WO2018149754A1 - Pyridine compounds - Google Patents
Pyridine compounds Download PDFInfo
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- WO2018149754A1 WO2018149754A1 PCT/EP2018/053332 EP2018053332W WO2018149754A1 WO 2018149754 A1 WO2018149754 A1 WO 2018149754A1 EP 2018053332 W EP2018053332 W EP 2018053332W WO 2018149754 A1 WO2018149754 A1 WO 2018149754A1
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- 0 *C(F)=C([N+]([O-])=O)S Chemical compound *C(F)=C([N+]([O-])=O)S 0.000 description 14
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
Definitions
- the present invention relates to the use of pyridine compounds and the N-oxides and the salts thereof for combating phytopathogenic fungi, and to the novel compound and methods for combating phytopathogenic fungi and to seeds coated with at least one such compound.
- the invention also relates to to compositions comprising at least one compound I .
- the fungicidal activity of the known fungicidal compounds is unsatisfactory. Based on this, it was an object of the present invention to provide compounds having improved activity and/or a broader activity spectrum against phytopathogenic harmful fungi.
- R 1 is in each case independently selected from H, halogen, OH, CN, NO2, SH, NH2, NH(Ci- C 4 -alkyl), N(Ci-C 4 -alkyl) 2 , NH-S0 2 -R x , Ci-C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, Ci-C 6 - alkoxy, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the het- eroaryl contains one, two or three heteroatoms selected from N, O and S; wherein
- R x is Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl, unsubstituted aryl or aryl that is substituted with substituents R x1 independently selected from Ci-C 4 -alkyl, halogen, OH, CN, Ci-C 4 -halogenalkyl, Ci-C 4 -alkoxy and Ci-C 4 -halogenalkoxy;
- R 1 wherein the acyclic moieties of R 1 are unsubstituted or substituted with groups R 1a which independently of one another are selected from:
- R 1a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C 4 - halogenalkoxy, Ci-C6-alkylthio, aryl and phenoxy, wherein the aryl and phenoxy group is unsubstituted or substituted with substituents R 11a selected from the group consisting of halogen, OH, Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl, Ci-C 4 -alkoxy and Ci-C 4 -halogenalkoxy;
- R 1 wherein the carbocyclic, heteroaryl and aryl moieties of R 1 are unsubstituted or substituted with groups R 1b which independently of one another are selected from: R 1 b halogen, OH, CN , Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C 4 -halogenalkyl, C 3 -C 6 -cycloalkyl, C3-C6-halogencycloalkyl, Ci-C 4 -halogenalkoxy and Ci-C6-alkylthio;
- heteroaryl is in each case independently selected from H, halogen, OH, CN, NO2, SH, NH2, NH(Ci- C 4 -alkyl), N(Ci-C 4 -alkyl) 2 , NH-S0 2 -R x , Ci-C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, Ci-C 6 - alkoxy, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; wherein R x is as defined above;
- R 2 wherein the acyclic moieties of R 2 are unsubstituted or substituted with groups R 2a which independently of one another are selected from:
- R 2a halogen, OH, CN , Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci- C 4 -halogenalkoxy, Ci-C6-alkylthio, aryl and phenoxy, wherein the aryl and phe- noxy group is unsubstituted or substituted with substituents R 22a selected from the group consisting of halogen, OH , Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl, C1-C4- alkoxy and Ci-C 4 -halogenalkoxy;
- R 2 wherein the carbocyclic, heteroaryl and aryl moieties of R 2 are unsubstituted or substituted with groups R 2b which independently of one another are selected from:
- R 2b halogen, OH, CN , Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C 4 -halogenalkyl, C 3 -C 6 -cyclo- alkyl, C3-C6-halogencycloalkyl, Ci-C 4 -halogenalkoxy and Ci-C6-alkylthio;
- halogen is in each case independently selected from halogen, OH , CN, NO2, SH, NH2, NH(Ci-C 4 -alkyl), N(Ci-C 4 -alkyl) 2 , N H(C 2 -C 4 -alkenyl), N(C 2 -C 4 -alkenyl) 2 , N H(C 2 -C 4 -al- kynyl), N(C 2 -C 4 -alkynyl) 2 , N H(C 3 -C 6 -cycloalkyl), N(C 3 -C 6 -cycloalkyl) 2 , N(Ci-C 4 -alkyl)(C 2 - C 4 -alkenyl), N(Ci-C 4 -alkyl)(C 2 -C 4 -alkynyl), N(Ci-C 4 -alkyl)(C 3 -C 6 -cycloalkyl), N(C 2
- R Y is Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6- alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, phenyl and phenyl-Ci-C6-alkyl; wherein the phenyl groups are unsubstituted or or carry one, two, three, four or five substituents selected from the group consisting of CN, halogen, OH , Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl, Ci-C 4 -alkoxy and C1-C4- halogenalkoxy;
- R 3 wherein the acyclic moieties of R 3 are unsubstituted or substituted with groups R 3a which independently of one another are selected from:
- R 3a halogen, OH, CN , Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4- halogenalkoxy, Ci-C6-alkylthio, aryl and phenoxy; wherein the aryl and phenoxy group is unsubstituted or substituted with substituent R 31a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
- R 3 wherein the carbocyclic, heteroaryl and aryl moieties of R 3 are unsubstituted or substituted with groups R 3b which independently of one another are selected from:
- R 3b halogen, OH, CN, Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C 4 -halogenalkyl, C 3 -C 6 -cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio;
- R 4 is in each case independently selected from halogen, OH, CN, NO2, SH, NH2,
- R Y is Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6- alkynyl, C2-C6-halogenalkynyl, C 3 -C6-cycloalkyl, C 3 -C6-halogencycloalkyl, phenyl and phenyl-Ci-C6-alkyl; wherein the phenyl groups are unsubstituted or or carry one, two, three, four or five substituents selected from the group consisting of CN, halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and C1-C4- halogenalkoxy;
- R 4 wherein the acyclic moieties of R 4 are unsubstituted or substituted with groups R 4a which independently of one another are selected from:
- R 4a halogen, OH, CN, d-Ce-alkoxy, C 3 -C6-cycloalkyl, C 3 -C6-halogencycloalkyl, C1-C4- halogenalkoxy, Ci-C6-alkylthio, aryl and phenoxy; wherein the aryl and phenoxy group is unsubstituted or substituted with substituent R 41a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
- R 4 wherein the carbocyclic, heteroaryl and aryl moieties of R 4 are unsubstituted or substituted with groups R 4b which independently of one another are selected from:
- R 4b halogen, OH, CN, Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C 4 -halogenalkyl, C 3 -C 6 -cycloalkyl, C 3 -C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio;
- R 34 wherein the acyclic moieties of R 34 are unsubstituted or substituted with identical or different groups R 34a which independently of one another are selected from:
- R 34a halogen, OH, CN, d-Ce-alkoxy, Cs-Ce-cycloalkyl, Cs-Ce-halogencycloal- kyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, aryl and phenoxy; wherein the aryl and phenoxy group is unsubstituted or substituted with R 341a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogen- alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy, CN, C3-C6-cycloalkyl, C3-C6- halogencycloalkyl, Ci-C4-alkylthio;
- R 34 wherein the carbocyclic, heterocyclic, heteroaryl and aryl moieties of R 34 are unsubstituted or substituted with identical or different groups R 34b which independently of one another are selected from:
- R 34b halogen, OH, CN, Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C 4 -halogenalkyl, Cs-Ce- cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, and Ci-C6-al- kylthio;
- R 6 together with the carbon atoms to which they are bound form a phenyl or five- or six membered heteroaryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S, and wherein the phenyl or heteroaryl is substituted with (R 56 ) 0 , wherein
- o 0, 1 , 2 or 3;
- R' and R" are independently selected from H , Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl or aryl; wherein the heterocycle or heteroaryl contains one, two or three heteroatoms selected from N, O and S, and wherein R' and R" are independently unsubstituted or substituted with R'" which is independently selected from halogen, OH , CN, N0 2 , SH, NH 2 , NH(Ci-C 4 -alkyl), N(Ci-C 4 -alkyl) 2 , NH-SO2- R x , Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogen
- R 56 wherein the acyclic moieties of R 56 are not further substituted or carry 1 , 2, 3 or up to the maximum possible number of identical or different groups R 56a which independently of one another are selected from:
- R 56a halogen, OH, CN , Ci-C 6 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 3 -C 6 - halogencycloalkyl, C3-C6-halogencycloalkenyl, Ci-C 4 -halogenalkoxy, Ci-C6-al- kylthio, five- or six-membered heteroaryl, phenyl and phenoxy; wherein the heteroaryl, phenyl and phenoxy group is unsubstituted or unsubstituted or substituted with R 561a selected from the group consisting of halogen, OH, Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl, Ci-C 4 -alkoxy and Ci-C 4 -halogenalkoxy;
- R 56 wherein the carbocyclic, phenyl, heterocyclic and heteroaryl moieties of R 56 are unsubstituted or substituted with identical or different groups R 56b which independently of one another are selected from:
- R 56b halogen, OH, CN , Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C 4 -halogenalkyl, C 3 -C 6 -cycloalkyl, C3-C6-halogencycloalkyl, Ci-C 4 -halogenalkoxy, and Ci-C6-alkylthio; is O or S;
- p 0, 1 or 2;
- R 7a , R 8a halogen, OH , CN , N0 2 , SH , N H 2 , N H(Ci-C 4 -alkyl), N(Ci-C 4 -alkyl) 2 , N
- n 0, 1 , 2;
- R 7 and R 8 are independently not further substituted or carry 1 , 2, 3, 4, 5 or up to the maximum number of identical or different groups R 7b or R 8b , respectively, which independently of one another are selected from:
- R 7b , R 8b halogen, OH , CN , N0 2 , SH , N H 2 , N H(Ci-C 4 -alkyl), N (Ci-C 4 -alkyl) 2 , N
- R x and n is as defined above;
- R 8 together with the carbon atom to which they are bound form a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle; wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, wherein the heteroatom N may carry one substituent selected from Ci-C4-alkyl, Ci-C4-halogenalkyl and S02Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted with one, two or three substituents selected from CN, C1-C4- alkyl, halogen, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy; and wherein the heteroatom S may be in the form of its oxide SO or SO2, and wherein the carbocycle or heterocycle is unsubstituted or carries one, two, three or four substituents R 78
- R 9 is in each case independently selected from H, OH, CN, SH, NH 2 , NH(Ci-C 4 -alkyl), N(Ci- C 4 -alkyl) 2 , NH-S0 2 -R x , Ci-C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, Ci-C 6 -alkoxy, C 3 -C 6 -cy- cloalkyl, saturated or partially unsaturated three-, four-, five-, six-, seven, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl and aryl;
- R x is as defined above;
- R 9 wherein the acyclic moieties of R 9 are unsubstituted or carry 1 , 2, 3 or up to the maximum possible number of identical or different groups R 9a which independently of one another are selected from:
- R 9a halogen, OH, CN , d-Ce-alkoxy, Cs-Ce-cycloalkyl, Cs-Ce-halogencycloalkyl, Ci- C4-halogenalkoxy, Ci-C6-alkylthio, aryl and phenoxy, wherein the aryl and phenyl group is unsubstituted or unsubstituted or substituted with R 9a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy, CN, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-al- kylthio;
- R 9 wherein the carbocyclic, heterocyclic, heteroaryl and aryl moieties of R 9 are unsubstituted or substituted with identical or different groups R 9b which independently of one another are selected from:
- R 9b halogen, OH, CN , Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C 4 -halogenalkyl, Cs-Ce-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, and Ci-C6-alkylthio; and the N-oxides and the agriculturally acceptable salts of the compounds of formula I for combating phytopathogenic fungi.
- the numbering of the ring members in the compounds of the present invention is as given in formula I above:
- the numbering of the ring members and substituents in the compounds of the present invention is as given in formula I above.
- intermediates IV can be accessed by starting from compounds of the formula VI and VII upon treatment with NaH in apolar or dipolar aprotic solvents at room temperature. Subsequent reduction e.g. with Fe in AcOH gives intermediates IV (see: Bioorganic & Medicinal Chemistr 15(17), 5912-5949; 2007).
- the N-oxides may be prepared from the inventive compounds according to conventional oxida- tion methods, e. g. by treating compounds I with an organic peracid such as metachloroper- benzoic acid (cf. WO 03/64572 or J. Med. Chem. 38(1 1 ), 1892-903, 1995); or with inorganic oxidizing agents such as hydrogen peroxide (cf. J. Heterocyc. Chem. 18(7), 1305-8, 1981 ) or ox- one (cf. J. Am. Chem. Soc. 123(25), 5962-5973, 2001 ).
- the oxidation may lead to pure mono- N-oxides or to a mixture of different N-oxides, which can be separated by conventional methods such as chromatography.
- C n -C m indicates the number of carbon atoms possible in each case in the substituent or substituent moiety in question.
- halogen refers to fluorine, chlorine, bromine and iodine.
- Ci-C6-alkyl refers to a straight-chained or branched saturated hydrocarbon group having 1 to 6 carbon atoms, e.g. methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 -methylpropyl, 2- methylpropyl, 1 ,1 -dimethylethyl, pentyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dime- thylpropyl, 1 -ethylpropyl, 1 ,1 -dimethylpropyl, 1 ,2-dimethylpropyl, hexyl, 1 -methylpentyl, 2- methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 ,1 -dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3-dimethyl- butyl, 2,2-dimethylbutyl
- C2-C4-alkyl refers to a straight-chained or branched alkyl group having 2 to 4 carbon atoms, such as ethyl, propyl (n-propyl), 1 -methylethyl (iso-propoyl), butyl, 1 -methylpropyl (sec- butyl), 2-methylpropyl (iso-butyl), 1 ,1 -dimethylethyl (tert. -butyl).
- Ci-C6-halogenalkyl refers to an alkyl group having 1 or 6 carbon atoms as defined above, wherein some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above.
- Examples are "Ci-C2-halogenalkyl” groups such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlor- ofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1 -chloroethyl, 1 -bromoethyl, 1 -fluoro- ethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro- 2,2-difluoroethyl, 2,2-dichloro-2-fluoroe
- Ci-C6-hydroxyalkyl refers to an alkyl group having 1 or 6 carbon atoms as defined above, wherein some or all of the hydrogen atoms in these groups may be replaced by OH groups.
- Ci-C4-alkoxy-Ci-C4-alkyl refers to alkyl having 1 to 4 carbon atoms (as defined above), whereAccording to one hydrogen atom of the alkyl radical is replaced by a Ci-C4-alkoxy group (as defined above).
- Ci-C4-alkoxy-Ci-C4-alkyl refers to alkyl having 1 to 4 carbon atoms (as defined above), whereAccording to one hydrogen atom of the alkyl radi- cal is replaced by a Ci-C6-alkoxy group (as defined above).
- C2-C6-alkenyl refers to a straight-chain or branched unsaturated hydrocarbon radical having 2 to 6 carbon atoms and a double bond in any position.
- Examples are “C2-C4-alkenyl” groups, such as ethenyl, 1 -propenyl, 2-propenyl (allyl), 1 -methylethenyl, 1 -butenyl, 2-butenyl, 3-butenyl, 1 -methyl-1 -propenyl, 2-methyl-1 -propenyl, 1 -methyl-2-propenyl, 2-methyl-2-propenyl.
- C2-C6-alkynyl refers to a straight-chain or branched unsaturated hydrocarbon radical having 2 to 6 carbon atoms and containing at least one triple bond.
- Examples are "C2-C4-al- kynyl” groups, such as ethynyl, prop-1 -ynyl, prop-2-ynyl (propargyl), but-1 -ynyl, but-2-ynyl, but- 3-ynyl, 1 -methyl-prop-2-ynyl.
- Ci-C6-alkoxy refers to a straight-chain or branched alkyl group having 1 to 6 carbon atoms which is bonded via an oxygen, at any position in the alkyl group.
- Examples are “C1-C4- alkoxy” groups, such as methoxy, ethoxy, n-propoxy, 1 -methylethoxy, butoxy, 1 -methyhprop- oxy, 2-methylpropoxy or 1 ,1 -dimethylethoxy.
- Ci-C6-halogenalkoxy refers to a Ci-C6-alkoxy radical as defined above, wherein some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as men- tioned above.
- Ci-C4-halogenalkoxy groups, such as OCH2F, OCHF2, OCF3, OCH2CI, OCHCI2, OCCI3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chlorothoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoro- ethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2- trichloroethoxy, OC2F5, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy,
- 2,3-difluoro-"propoxy 2 chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3 bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH2-C2F5, OCF2-C2F5, 1 -fluo- romethyl-2-fluoroethoxy, 1 -chloromethyl-2-chloroethoxy, 1 -bromomethyl-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy.
- C2-C6-alkenyloxy refers to a straight-chain or branched alkenyl group having 2 to 6 carbon atoms which is bonded via an oxygen, at any position in the alkenyl group. Examples are “C2-C4-alkenyloxy” groups.
- C2-C6-alkynyloxy refers to a straight-chain or branched alkynyl group having 2 to 6 carbon atoms which is bonded via an oxygen, at any position in the alkynyl group. Examples are “C2-C4-alkynyloxy” groups.
- C3-C6-cycloalkyl refers to monocyclic saturated hydrocarbon radicals having 3 to 6 carbon ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl. Accordingly, a saturated three-, four-, five-, six-, seven-, eight-, nine or ten-membered carbocyclyl or carbo- cycle is a "C3-Cio-cycloalkyl".
- C3-C6-cycloalkenyl refers to a monocyclic partially unsaturated 3-, 4- 5- or 6-mem- bered carbocycle having 3 to 6 carbon ring members and at least one double bond, such as cy- clopentenyl, cyclopentadienyl, cyclohexadienyl. Accordingly, a partially unsaturated three-, four- , five-, six-, seven-, eight-, nine or ten-membered carbocyclyl or carbocycle is a "C3-Cio-cycloal- kenyl".
- C3-C8-cycloalkyl-Ci-C4-alkyl refers to alkyl having 1 to 4 carbon atoms (as defined above), whereAccording to one hydrogen atom of the alkyl radical is replaced by a cycloalkyl radical having 3 to 8 carbon atoms (as defined above).
- Ci-C6-alkylthio refers to straight-chain or branched alkyl groups having 1 to 6 carbon atoms (as defined above) bonded via a sulfur atom. Accordingly, the term “Ci- C6-halogenalkylthio” as used herein refers to straight-chain or branched halogenalkyi group hav- ing 1 to 6 carbon atoms (as defined above) bonded through a sulfur atom, at any position in the halogenalkyi group.
- the number of valence of carbon is 4, that of nitrogen is 3.
- saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine or ten- membered heterocyclyl or heterocycle, wherein the heterocyclyl or heterocycle contains 1 , 2, 3 or 4 heteroatoms selected from N, O and S is to be understood as meaning both saturated and partially unsaturated heterocycles, wherein the ring member atoms of the heterocycle include besides carbon atoms 1 , 2, 3 or 4 heteroatoms independently selected from the group of O, N and S.
- saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine or ten- membered heterocyclyl or heterocycle, wherein the heterocyclyl or heterocycle contains 1 , 2, 3 or 4 heteroatoms selected from N, O and S is to be understood as meaning both saturated and partially unsaturated heterocycles, wherein the ring member atoms of the heterocycle include besides carbon atoms 1 , 2, 3 or 4 heteroatoms independently selected from the group of O, N and
- a 3- or 4-membered saturated heterocycle which contains 1 or 2 heteroatoms from the group consisting of O, N and S as ring members such as oxirane, aziridine, thiirane, oxetane, azet- idine, thiethane, [1 ,2]dioxetane, [1 ,2]dithietane, [1 ,2]diazetidine; and
- a 5- or 6-membered saturated or partially unsaturated heterocycle which contains 1 , 2 or 3 heteroatoms from the group consisting of O, N and S as ring members such as 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isox- azolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazoli- dinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazoli- dinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imi
- a 7-membered saturated or partially unsaturated heterocycle such as tetra- and hexahydroaze- pinyl, such as 2,3,4, 5-tetrahydro[1 H]azepin-1 -,-2-,-3-,-4-,-5-,-6- or-7-yl, 3,4,5,6-tetrahy- dro[2H]azepin-2-,-3-,-4-,-5-,-6- or-7-yl, 2,3,4,7-tetrahydro[1 H]azepin-1 -,-2-,-3-,-4-,-5-,-6- or-7-yl, 2,3,6,7-tetrahydro[1 H]azepin-1 -,-2-,-3-,-4-,-5-,-6- or-7-yl, hexahydroazepin-1 -,-2-,-3- or-4-yl, tetra- and hexahydrooxepinyl such as 2,3,4,5-tetrahydr
- 5-or 6-membered heteroaryl or “5-or 6-membered heteroaromatic” refers to aromatic ring systems incuding besides carbon atoms, 1 , 2, 3 or 4 heteroatoms independently selected from the group consisting of N, O and S, for example,
- a 5-membered heteroaryl such as pyrrol-1 -yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan- 2-yl, furan-3-yl, pyrazol-1 -yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1 -yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-
- a 6-membered heteroaryl such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyri- dazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl.
- Agriculturally acceptable salts of the inventive compounds encompass especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the fungicidal action of said compounds.
- Suitable cations are thus in particular the ions of the alkali metals, preferably sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, of the transition metals, preferably manga- nese, copper, zinc and iron, and also the ammonium ion which, if desired, may carry one to four Ci-C4-alkyl substituents and/or one phenyl or benzyl substituent, preferably diisopropylammo- nium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C4-alkyl)sulfonium, and s
- Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogensulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting such inventive compound with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
- the inventive compounds can be present in atropisomers arising from restricted rotation about a single bond of asymmetric groups. They also form part of the subject matter of the present invention.
- the compounds of formula I and their N-oxides may have one or more centers of chirality, in which case they are present as pure enantiomers or pure di- astereomers or as enantiomer or diastereomer mixtures. Both, the pure enantiomers or dia- stereomers and their mixtures are subject matter of the present invention.
- R 1 is in each case independently selected from hydrogen, halogen, OH, CN, N0 2 , SH, NH 2 , NH(Ci-C 4 -alkyl), N(Ci-C 4 -alkyl) 2 , NH-S0 2 -R x , Ci-C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C6-alkynyl, Ci-C6-alkoxy, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl;
- heteroaryl contains one, two or three heteroatoms selected from N, O and S; and wherein
- R x is Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl, unsubstituted aryl or aryl that is substituted with one, two, three, four or five substituents R x1 independently selected from Ci-C 4 -alkyl, halogen, OH, CN, Ci-C 4 -halogenalkyl, Ci-C 4 -alkoxy and Ci-C 4 -halogenalkoxy;
- R 1 wherein the acyclic moieties of R 1 are unsubstituted or substituted with identical or different groups R 1a which independently of one another are selected from:
- R 1a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalky, Ci-C 4 -halogen- alkoxy, Ci-C6-alkylthio, aryl and phenoxy, wherein the aryl and phenoxy group is unsubstituted or unsubstituted or substituted with R 11a selected from the group consisting of halogen, OH, Ci- C 4 -alkyl, Ci-C 4 -halogenalkyl, Ci-C 4 -alkoxy and Ci-C 4 -halogenalkoxy;
- R 1 wherein the carbocyclic, heteroaryl and aryl moieties of R 1 are unsubstituted or substituted with identical or different groups R 1b which independently of one another are selected from:
- R 1b halogen, OH, CN, Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C 4 -halogenalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 - halogencycloalkyl, Ci-C 4 -halogenalkoxy and Ci-C6-alkylthio.
- R 1 is H, halogen or Ci-C6-alkyl, in particular H, CH3, Et, F, CI, more specifically H, CH3, F or CI most preferred H, F or CI.
- R 1 is hydrogen
- R 1 is halogen, in particular Br, F or CI, more specifically F or CI.
- R 1 is F
- R 1 is CI
- R 1 is Br.
- R 1 is OH
- R 1 is CN
- R 1 is N0 2 .
- R 1 is SH.
- R 1 is NH 2 , NH(Ci-C 4 -alkyl), N(Ci-C 4 -alkyl) 2 or NH-S0 2 -R x , wherein R x is Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl, unsubstituted aryl or aryl that is substituted with one, two, three, four or five substituents R x1 independently selected from Ci-C 4 -al- kyl, halogen, OH, CN, Ci-C 4 -halogenalkyl, Ci-C 4 -alkoxy, or Ci-C 4 -halogenalkoxy.
- Ci-C4-alkyl such as NHCH3 and N(CH3)2.
- R x is Ci-C4-alkyl, and phenyl that is substituted with one CH3, more specifically S02-R x is CH3 and tosyl group ("Ts").
- R 1 is Ci-C6-alkyl, in particular Ci-C4-alkyl,
- R 1 is Ci-C6-halogenalkyl, in particular C1-C4- halogenalkyl, such as CF 3 , CHF 2 , CH 2 F, CCI 3 , CHCI2, CH 2 CI, CF3CH2, CCI3CH2 or CF 2 CHF 2 .
- R 1 is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C 2 -C 4 -alkynyl or C 2 -C 4 -halogenalkynyl, such as C ⁇ CH, C ⁇ CCI, C ⁇ CF. CH 2 C ⁇ CH, CH 2 C ⁇ CCI, or CH 2 C ⁇ CF.
- R 1 is Ci-C6-alkoxy, in particular Ci-C4-alkoxy, more specifically Ci-C2-alkoxy such as OCH3 or OCH2CH3.
- R 1 is Ci-C6-halogenalkoxy, in particular Ci- C4-halogenalkoxy, more specifically Ci-C2-halogenalkoxy such as OCF3, OCHF2, OCH2F, OCCI3, OCHC or OCH2CI, in particular OCF 3 , OCHF 2 , OCCI 3 or OCHCI 2 .
- R 1 is C3-C6-cycloalkyl, in particular cyclopro- pyl.
- R 1 is C3-C6-cycloalkyl, for example cyclopro- pyl, substituted with one, two, three or up to the maximum possible number of identical or different groups R 1b as defined and preferably herein.
- R 1 is C3-C6-halogencycloalkyl.
- R 1 is fully or partially halogenated cyclopropyl.
- R 1 is unsubstituted aryl or aryl that is substituted with one, two, three or four R 1b , as defined herein.
- R 1 is unsubstituted phenyl or phenyl that is substituted with one, two, three or four R 1b , as defined herein.
- R 1 is unsubstituted 5- or 6-membered heteroaryl. According to still a further embodiment, R 1 is 5- or 6-membered heteroaryl that is substituted with one, two or three R 1b , as defined herein.
- R 1 is in each case independently selected from hydrogen, halogen, OH, CN, N0 2 , SH, NH 2 , NH(Ci-C 4 -alkyl), N(Ci-C 4 -alkyl) 2 , NH-S0 2 -R x , Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy and C3-C6-cycloalkyl; wherein the acyclic moieties of R 1 are not further substituted or carry one, two, three, four or five identical or different groups R 1a as defined below and wherein the carbocyclic, heteroaryl and aryl moieties of R 1 are not further substituted or carry one, two, three, four or five identical or different groups R 1b as defined below.
- R 1 is independently selected from hydrogen, halogen, OH, Ci-C6-alkyl, Ci-C6-halogenalkyl, Ci-C6-alkoxy and Ci-C6-halogenalkoxy, in particular independently selected from H, F, CI, Br, CN, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, C1-C4- alkoxy and Ci-C4-halogenalkoxy.
- R 1a are the possible substituents for the acyclic moieties of R 1 .
- R 1a is independently selected from halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, aryl and phe- noxy, wherein the aryl and phenoxy group is unsubstituted or unsubstituted or substituted with R 11a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, C1-C4- alkoxy and Ci-C4-halogenalkoxy, in particular selected from halogen, Ci-C2-alkyl, Ci-C2-halo- genalkyl, Ci-C2-alkoxy and Ci-C2-halogenalkoxy, more specifically selected from halogen, such as F, CI and Br.
- halogen such as F, CI and Br.
- R 1a is independently selected from halogen, OH, CN, Ci-C2-alkoxy, C3- C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C2-halogenalkoxy. Specifically, R 1a is
- R 1a is independently selected from halogen, such as F, CI, Br and I, more specifically F, CI and Br.
- R 1a is independently selected from OH, C3- C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C2-halogenalkoxy. Specifically, R 1a is
- R 1a is independently selected from aryl and phenoxy, wherein the aryl and phenoxy group is unsubstituted or substituted with R 11a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci- C4-halogenalkoxy, in particular selected from halogen, Ci-C2-alkyl, Ci-C2-halogenalkyl, C1-C2- alkoxy and Ci-C2-halogenalkoxy, more specifically selected from halogen, such as F, CI and Br.
- R 11a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci- C4-halogenalkoxy, in particular selected from halogen, Ci-C2-alkyl, Ci-C2-halogenalkyl, C1-C2- alkoxy and Ci-C2-
- R 1b are the possible substituents for the carbocyclic, heteroaryl and aryl moieties of R 1 .
- R 1b according to the invention is independently selected from halogen, OH, CN, Ci-C4-alkyl, Ci- C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C4-halogen- alkoxy.
- R 1b is independently selected from halogen, CN, C1-C2- alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and C1-C2- halogenalkoxy.
- R 1b is independently selected from F, CI, Br, OH, CN, CH3, OCH3, CHF2, OCHF2, cyclopropyl, 1 -F-cyclopropyl, 1 -CI-cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1 -C - cyclopropyl, OCF 3 , and OCHF 2 .
- R 1b is independently selected from halogen, Ci- C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and C1-C2- halogenalkoxy.
- R 1b is independently selected from halogen, CN, OH, CH3, CHF2, OCHF2, OCF3, OCH3, cyclopropyl, 1 -F-cyclopropyl, 1 -CI-cyclopropyl, 1 ,1 -F 2 -cyclopropyl, 1 ,1 -C - cyclopropyl and halogenmethoxy, more specifically independently selected from F, CI, OH, CH3, OCH3, CHF 2 , OCH3, cyclopropyl, 1 -F-cyclopropyl, 1 -CI-cyclopropyl, 1 ,1 -F 2 -cyclopropyl, 1 ,1 -C - cyclopropyl, OCHF2 and OCF3.
- R x in the substituent NH-S02-R X is in each case independently selected from Ci-C4-alkyl, C1-C4- halogenalkyl, unsubstituted aryl and aryl that is substituted with one, two, three, four or five substituents R x1 independently selected from Ci-C4-alkyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy.
- R x is in each case independently selected from Ci-C4-alkyl, halogen, OH, CN and phenyl that is substituted with one, two or three R x1 independently selected from Ci-C2-alkyl, more specifically R x is in each case independently selected from Ci-C4-alkyl and phenyl that is substituted with one CH3, more specifically S02-R x is the tosyl group ("Ts").
- R 1 Particularly preferred embodiments of R 1 according to the invention are in Table P1 below, wherein each line of lines P1 -1 to P1 -16 corresponds to one particular embodiment of the invention. Thereby, for every R 1 that is present in the inventive compounds, these specific
- Ts stands for the tosylgroup S02-(p-CH3)phenyl.
- R 2 is in each case independently selected from hydrogen, halogen, OH, CN, N0 2 , SH, NH 2 , NH(Ci-C 4 -alkyl), N(Ci-C 4 -alkyl) 2 , NH-S0 2 -R x , Ci-C 6 -alkyl, C 2 -C 6 -alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl;
- heteroaryl contains one, two or three heteroatoms selected from N, O and S; and wherein
- R x is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted with one, two, three, four or five substituents R x2 independently selected from Ci-C4-alkyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
- R 2 wherein the acyclic moieties of R 2 are unsubstituted or substituted with identical or different groups R 2a which independently of one another are selected from:
- R 2a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalky, Ci-C4-halogen- alkoxy, Ci-C6-alkylthio, aryl and phenoxy, wherein the aryl and phenoxy group is unsubstituted or substituted with R 21a selected from the group consisting of halogen, OH, Ci-C4-alkyl, C1-C4- halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
- R 2 wherein the carbocyclic, heteroaryl and aryl moieties of R 2 are unsubstituted or substituted with identical or different groups R 2b which independently of one another are selected from:
- R 2b halogen, OH, CN, Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C 4 -halogenalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 - halogencycloalky, Ci-C4-halogenalkoxy and Ci-C6-alkylthio.
- R 2 is H, halogen or Ci-C6-alkyl, in particular H, CH3, Et, F, CI, more specifically H, CH3, F or CI most preferred H, F or CI.
- R 2 is halogen, in particular Br, F or CI, more specifically F or CI.
- R 2 is F
- R 2 is CI
- R 2 is Br
- R 2 is hydrogen
- R 2 is OH
- R 2 is CN
- R 2 is N0 2 .
- R 2 is SH.
- R 2 is NH 2 , NH(Ci-C 4 -alkyl), N(Ci-C 4 -alkyl) 2 or NH-S0 2 -R x , wherein R x is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted with one, two, three, four or five substituents R x2 independently selected from Ci-C4-alkyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy, or Ci-C4-halogenalkoxy.
- Ci-C4-alkyl such as NHCH3 and N(CH3) 2 .
- R x is Ci-C4-alkyl, and phenyl that is substituted with one CH3, more specifically S0 2 -R x is CH3 and tosyl group ("Ts").
- R 2 is Ci-C6-alkyl, in particular Ci-C4-alkyl, such as CH 3 or CH 2 CH 3 .
- R 2 is Ci-C6-halogenalkyl, in particular C1-C4- halogenalkyl, such as CF 3 , CHF 2 , CH 2 F, CCI 3 , CHCI 2 , CH 2 CI, CF 3 CH 2 , CCI 3 CH 2 or CF 2 CHF 2 .
- R 2 is C 2 -C6-alkynyl or C 2 -C6-halogenalkynyl, in particular C 2 -C 4 -alkynyl or C 2 -C 4 -halogenalkynyl, such as C ⁇ CH, C ⁇ CCI, C ⁇ CF. CH 2 C ⁇ CH, CH 2 C ⁇ CCI, or CH 2 C ⁇ CF.
- R 2 is Ci-C6-alkoxy, in particular Ci-C4-alkoxy, more specifically Ci-C2-alkoxy such as OCH3 or OCH2CH3.
- R 2 is Ci-C6-halogenalkoxy, in particular Ci- C4-halogenalkoxy, more specifically Ci-C2-halogenalkoxy such as OCF3, OCHF2, OCH2F, OCCIs, OCHC or OCH2CI, in particular OCF 3 , OCHF 2 , OCCI 3 or OCHCI 2 .
- R 2 is C3-C6-cycloalkyl, in particular cyclopropyl.
- R 2 is C3-C6-cycloalkyl, for example cyclopropyl, substituted with one, two, three or up to the maximum possible number of identical or different groups R 2b as defined and preferably herein.
- R 2 is C3-C6-halogencycloalkyl.
- R 2 is fully or partially halogenated cyclopropyl.
- R 2 is unsubstituted aryl or aryl that is substituted with one, two, three or four R 2b , as defined herein.
- R 2 is unsubstituted phenyl or phenyl that is substituted with one, two, three or four R 2b , as defined herein.
- R 2 is unsubstituted 5- or 6-membered heteroaryl. According to still a further embodiment, R 2 is 5- or 6-membered heteroaryl that is substituted with one, two or three R 2b , as defined herein.
- R 2 is in each case independently selected from hydrogen, halogen, OH, CN, N0 2 , SH, NH 2 , NH(Ci-C 4 -alkyl), N(Ci-C 4 -alkyl) 2 , NH-S0 2 -R x , Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy and C3-C6-cycloalkyl; wherein the acyclic moieties of R 2 are not further substituted or carry one, two, three, four or five identical or different groups R 2a as defined below and wherein the cycloalkyl moieties of R 2 are not further substituted or carry one, two, three, four or five identical or different groups R 2b as defined below.
- R 2 is independently selected from hydrogen, halogen, OH, Ci-C6-alkyl, Ci-C6-halogenalkyl, Ci-C6-alkoxy and Ci-C6-halogenalkoxy, in particular independently selected from H, F, CI, Br, CN, OH, Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl, C1-C4- alkoxy and Ci-C 4 -halogenalkoxy.
- R 2a are the possible substituents for the acyclic moieties of R 2 .
- R 2a is independently selected from halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalky, Ci-C 4 -halogenalkoxy, Ci-C6-alkylthio, aryl and phenoxy, wherein the aryl and phenoxy group is unsubstituted or substituted with R 22a selected from the group consisting of halogen, OH, Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl, Ci-C 4 -alkoxy and C1-C4- halogenalkoxy, in particular selected from halogen, Ci-C2-alkyl, Ci-C2-halogenalkyl, C1-C2- alkoxy and Ci-C2-halogenalkoxy, more specifically selected from halogen, such as F, CI and Br.
- halogen such as F, CI and Br.
- R 2a is independently selected from halogen, OH, CN, C1-C2- alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalky and Ci-C2-halogenalkoxy.
- R 2a is independently selected from F, CI, OH, CN, Ci-C2-alkoxy, cyclopropyl, 1 -F-cyclopropyl, 1 -CI- cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1 -Cl2-cyclopropyl and Ci-C2-halogenalkoxy.
- R 2a is independently selected from halogen, such as F, CI, Br and I, more specifically F, CI and Br.
- R 2a is independently selected from OH, C3- C6-cycloalkyl, C3-C6-halogencycloalky and Ci-C2-halogenalkoxy. Specifically, R 2a is
- R 2a is independently selected from aryl and phenoxy, wherein the aryl and phenoxy group is unsubstituted or substituted with R 22a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci- C4-halogenalkoxy, in particular selected from halogen, Ci-C2-alkyl, Ci-C2-halogenalkyl, C1-C2- alkoxy and Ci-C2-halogenalkoxy, more specifically selected from halogen, such as F, CI and Br.
- R 22a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci- C4-halogenalkoxy, in particular selected from halogen, Ci-C2-alkyl, Ci-C2-halogenalkyl, C1-C2- alkoxy and Ci-C2-
- R 2b are the possible substituents for the carbocyclic, heteroaryl and aryl moieties of R 2 .
- R 2b according to the invention is independently selected from halogen, OH, CN, Ci-C4-alkyl, Ci- C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalky and Ci-C4-halogen- alkoxy.
- R 2b is independently selected from halogen, CN, C1-C2- alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and C1-C2- halogenalkoxy.
- R 2b is independently selected from F, CI, Br, OH, CN, CH3, OCH3, CHF2, OCHF2, cyclopropyl, 1 -F-cyclopropyl, 1 -CI-cyclopropyl 1 ,1 -F2-cyclopropyl, 1 ,1 -C - cyclopropyl, OCF3, and OCHF2.
- R 2b is independently selected from halogen, Ci- C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and C1-C2- halogenalkoxy.
- R 2b is independently selected from halogen, OH, CH3, OCH3, CN, CHF2, OCHF2, OCF3, OCH3 cyclopropyl, 1 -F-cyclopropyl, 1 -CI-cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1 -Cl2-cyclopropyl and halogenmethoxy, more specifically independently selected from F, CI, OH, CH3, OCH3, CHF2, OCH3, cyclopropyl, 1 -F-cyclopropyl, 1 -CI-cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1 -CI 2 -cyclopropyl, OCHF 2 and OCF 3 .
- R 2 according to the invention are in Table P2 below, wherein each line of lines P2-1 to P2-16 corresponds to one particular embodiment of the invention. Thereby, for every R 2 that is present in the inventive compounds, these specific
- Ts stands for the tosylgroup S02-(p-CH3)phenyl.
- R 3 is in each case independently selected from halogen, OH , CN , NO2, SH , N H2, N H(Ci-C 4 - alkyl), N(Ci-C 4 -alkyl) 2 , N H(C 2 -C 4 -alkenyl), N(C 2 -C 4 -alkenyl) 2 , N H(C 2 -C 4 -alkynyl), N(C 2 -C 4 - alkynyl) 2 , N H(C 3 -C 6 -cycloalkyl), N(C 3 -C 6 -cycloalkyl) 2 , N(C2-C 4 -alkyl)(C2-C 4 -alkenyl), N(C 2 -C 4 - alkyl)(C 2 -C 4 -alkynyl), N(C2-C 4 -alkyl)(C 3 -C6-cycloalkyl), N(C2-C 4 -alken
- heteroaryl contains one, two or three heteroatoms selected from N , O and S;
- R x is as defined above;
- R Y is Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6- alkynyl, C2-C6-halogenalkynyl, C 3 -C6-cycloalkyl, C 3 -C6-halogencycloalkyl; phenyl and phenyl-Ci-C6-alkyl; wherein the phenyl group is unsubstituted or substituted with substituents selected from the group consisting of halogen, CN , OH , C1-C6- alkyl, Ci-C6-halogenalkyl, Ci-C6-alkoxy and Ci-C6-halogenalkoxy; wherein the acyclic moieties of R 3 are unsubstituted or substituted with groups R 3a which independently of one another are selected from:
- R 3a halogen, OH , CN , Ci-C6-alkoxy, C 3 -C6-cycloalkyl, C 3 -C6-halogencycloalkyl, C1-C4- halogenalkoxy, Ci-C6-alkylthio, aryl and phenoxy, wherein the aryl and phenoxy group is unsubstituted or substituted with substituents R 31 a selected from the group consisting of halogen, OH , Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl, Ci-C 4 -alkoxy and Ci-C 4 -halogenalkoxy;
- R 3b halogen, OH , CN , Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C 4 -halogenalkyl, C 3 -C 6 -cyclo- alkyl, C 3 -C6-halogencycloalkyl, Ci-C 4 -halogenalkoxy and Ci-C6-alkylthio.
- R 3 is selected from the group consisting of halogen, CN , Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6- halogenalkynyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, C 3 -C6-cycloalkyl, C 3 -C6-halogencycloalkyl, and OR Y .
- R 3 is halogen, in particular F, CI, Br or I, more specifically F, CI or Br, in particular F or CI.
- R 3 is F.
- R 3 is CI.
- R 3 is Br.
- R 3 is OH.
- R 3 is CN.
- R 3 is N0 2 .
- R 3 is SH.
- R 3 is NH 2 .
- R 3 is , NH(C
- R 3 is , N(Ci- NH(C 2 H 5 ) 2 .
- R 3 is , NH(C
- R 3 is , NH(C3-C6-cycloalkyl), in particular NH(C 3 H 7 ), NH(C 4 H 9 ).
- R 3 is , N(C3-C6-cycloalkyl) 2 , in particular N(C 3 H 7 ) 2 , N(C 4 H 9 ) 2 .
- R 3 is N(Ci-C4-alkyl)(C 2 -C4-alkynyl), in particular N(CH 3 )(C ⁇ CH), N(CH 3 )(CH 2 C ⁇ CH), N(C 2 H 5 )(C ⁇ CH), N(C 2 H 5 )(CH 2 C ⁇ CH).
- R 3 is N(Ci-C4-alkyl)(C 3 -C6-cycloalkyl), in particular N(CH 3 )(C 3 H 7 ), N(CH 3 )(C 4 H 9 ), N(C 2 H 5 )(C 3 H 7 ), N(CH 3 )(C 4 H 9 ).
- R 3 is N(C2-C 4 -alkynyl)(C3-C6-cycloalkyl), in particular N(C ⁇ CH)(C 3 H 7 ), N(CH 2 C ⁇ CH)(C 4 H 9 ), N(C ⁇ CH)(C 3 H 7 ), N(CH 2 C ⁇ CH)(C 4 H 9 ).
- R 3 is NH-S0 2 -R x such as NH-S0 2 -CH 3 , NH-S0 2 -CH 2 -CH 3 , NH-S0 2 -CF 3 , NH-S0 2 -Ts.
- R 3 is S(0)n-C 2 -C6-alkenyl such as
- R 3 is Ci-C6-alkyl, in particular Ci-C4-alkyl, such as CH3. or C2H5, in particular CH3 or CH2CH3.
- R 3 is Ci-C6-halogenalkyl, in particular C1-C4- halogenalkyl, such as CF 3 , CCI 3 , FCH 2 , CICH 2 , F 2 CH, CI 2 CH, CF3CH2, CCI3CH2 or CF 2 CHF 2 .
- R 3 is OR Y , wherein R Y is Ci-C6-alkyl, Ci- C6-halogenalkyl, C 2 -C6-alkenyl, C 2 -C6-halogenalkenyl, C 2 -C6-alkynyl, C 2 -C6-halogenalkynyl, C3- C6-cycloalkyl, C3-C6-halogencycloalkyl.
- R 3 is OR Y , wherein R Y is Ci-C6-alkyl, in particular Ci-C 4 -alkyl, more specifically Ci-C 2 -alkoxy. R 3 is such as OCH3 or OCH2CH3.
- R 3 is OR Y , wherein R Y is Ci-C6-halogen- alkyl, in particular Ci-C 4 -halogenalkyl, more specifically Ci-C2-halogenalkyl.
- R 3 is such as OCF3, OCHF2, OCH2F, OCCI3, OCHC or OCH2CI, in particular OCF 3 , OCHF 2 , OCCI 3 or OCHCI 2 .
- R 3 is OR Y , wherein R Y C2-C6-alkenyl, in particular C2-C 4 -alkenyl, more specifically Ci-C2-alkenyl.
- R 3 is OR Y , wherein R Y C 2 -C6-halogen- alkenyl, in particular C2-C 4 -halogenalkenyl, more specifically Ci-C2-halogenalkenyl.
- R 3 is OR Y , wherein R Y C2-C6-alkynyl, in particular C2-C6-alkynyl, in particular C2-C 4 -alkynyl, more specifically Ci-C2-alkynyl.
- R 3 is such as OC ⁇ CH,
- R 3 is OR Y , wherein R Y C2-C6-halogen- alkynyl, in particular C2-C6-halogenalkynyl, in particular C2-C 4 -halogenalkynyl, more specifically Ci-C 2 -halogenalkynyl.
- R 3 is such as OC ⁇ CCI, OCH 2 C ⁇ CCI, or OCCI 2 C ⁇ CCI.
- R 3 is is OR Y , wherein R Y C3-C6-cycloalkenyl, in particular cyclopropenyl.
- R 3 is C3-C6-cycloalkyl, in particular cyclopro- pyl.
- R 3 is C3-C6-halogencycloalkyl.
- R 3b is fully or partially halogenated cyclopropyl, such as 1 -F-cyclopropyl, 1 -CI- cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1 -Cl2-cyclopropyl .
- R 3 is phenyl-Ci-C6-alkyl, such as phenyl- CH2, wherein the phenyl moiety in each case is unsubstituted or substituted with one, two or three identical or different groups R 3b which independently of one another are selected from halogen, Ci-C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl and Ci-C2-halogenalkoxy, in particular F, CI, Br, CH 3 , OCH3, CF 3 and OCF 3 .
- R 3 is aryl, in particular phenyl, wherein the aryl or phenyl moiety in each case is unsubstituted or substituted with identical or different groups R 3b which independently of one another are selected from CN, halogen, Ci-C2-alkyl, Ci- C2-alkoxy, Ci-C2-halogenalkyl and Ci-C2-halogenalkoxy, in particular CN, F, CI, Br, CH3, OCH3, CHF2, OCHF2, CF3 and OCF3.
- R 3 is unsubstituted phenyl.
- R 3 is phenyl, that is substituted with one, two or three, in particular one, halogen, in particular selected from F, CI and Br, more specifically selected from F and CI.
- R 3 is a 5-membered heteroaryl such as pyr- rol-1 -yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1 -yl, pyrazol- 3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1 -yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2- yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, is
- R 3 is a 6-membered heteroaryl such as pyri- din-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, py- rimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl.
- R 3 is in each case independently selected from H, halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6- alkoxy, Ci-C6-halogenalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyl and C3-C6- halogencycloalkyl, wherein the acyclic moieties of R 3 are unsubstituted or substituted with iden- tical or different groups R 3a as defined and preferably defined herein, and wherein the carbocy-rod, phenyl and heteroaryl moieties of R 3 are unsubstituted or substituted with identical or different groups R 3b as defined and preferably defined herein.
- R 3 is in each case independently selected from H, halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6- alkoxy, Ci-C6-halogenalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyl and C3-C6- halogencycloalkyl, wherein the acyclic moieties of R 3 are unsubstituted or substituted with identical or different groups R 3a as defined and preferably defined herein, and wherein the cycloalkyi moieties of R 3 are unsubstituted or substituted with identical or different groups R 3b as defined and preferably defined herein.
- R 3a are the possible substituents for the acyclic moieties of R 3 .
- R 3a is independently selected from halogen, OH, CN, C1-C6- alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, aryl and phenoxy, wherein the aryl and phenyl group is unsubstituted or substituted with substitu- ents R 31a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy.
- R 3a is independently selected from halogen, Ci-C6-alkoxy, C3-C6- cycloalkyl, C3-C6-halogencycloalkyl and Ci-C4-halogenalkoxy.
- R 3a is independently selected from F, CI, Br, I , Ci-C2-alkoxy, cyclopropyl, 1 -F-cyclopropyl, 1 -CI-cyclopropyl, I -F2- cyclopropyl, 1 ,1 -Cl2-cyclopropyl and Ci-C2-halogenalkoxy.
- R 3a is independently halogen, in particular selected from F, CI, Br and I , more specifically F, CI and Br.
- R 3b are the possible substituents for the carbocyclic, heteroaryl and phenyl moieties of R 3 .
- R 3b according to the invention is independently selected from halogen, OH, CN , Ci-C4-alkyl, C1-C4- alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and d-Ce-alkylthio.
- R 3b is independently selected from halogen, CN, C1-C4- alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl and Ci-C4-halogenalkoxy, in particular halogen, C1-C4- alkyl and Ci-C4-alkoxy.
- R 3b is independently selected from F, CI, CN, CH3, OCH3 and halogenmethoxy.
- R 3 Particularly preferred embodiments of R 3 according to the invention are in Table P3 below, wherein each line of lines P3-1 to P3-42 corresponds to one particular embodiment of the invention, wherein P3-1 to P3-42 are also in any combination with one another a preferred embodiment of the present invention.
- the connection point to the carbon atom, to which R 3 is bound is marked with "#" in the drawings.
- R 4 is in each case independently selected from halogen, OH, CN, N0 2 , SH, NH 2 , NH(Ci-C 4 - alkyl), N(Ci-C 4 -alkyl) 2 , NH(C 2 -C 4 -alkenyl), N(C 2 -C 4 -alkenyl) 2 , NH(C 2 -C 4 -alkynyl), N(C 2 -C 4 - alkynyl) 2 , NH(C 3 -C 6 -cycloalkyl), N(C 3 -C 6 -cycloalkyl) 2 , N(C 2 -C 4 -alkyl)(C 2 -C 4 -alkenyl), N(C 2 -C 4 - alkyl)(C 2 -C 4 -alkynyl), N(C 2 -C 4 -cycloalkyl), N(C 2 -C 4 -alkyl)
- heteroaryl contains one, two or three heteroatoms selected from N, O and S;
- R x is as defined above;
- R Y is as defined above;
- R 4 wherein the acyclic moieties of R 4 are unsubstituted or substituted with groups R 4a which independently of one another are selected from:
- R 4a halogen, OH, CN, d-Ce-alkoxy, C 3 -C6-cycloalkyl, C 3 -C6-halogencycloalkyl, C1-C4- halogenalkoxy, Ci-C6-alkylthio, aryl and phenoxy, wherein the aryl and phenyl group is unsubstituted or substituted with substituents R 41a selected from the group consisting of halogen, OH, Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl, Ci-C 4 -alkoxy and Ci-C 4 -halogenalkoxy;
- R 4 wherein the carbocyclic, heteroaryl and aryl moieties of R 4 are unsubstituted or substituted with groups R 4b which independently of one another are selected from:
- R 4b halogen, OH, CN, Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C 4 -halogenalkyl, C 3 -C 6 -cycloalkyl, C3-C6-halogencycloalkyl, Ci-C 4 -halogenalkoxy and Ci-C6-alkylthio.
- R 4 is selected from the group consisting of halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6- halogenalkynyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy and OR Y .
- R 4 is secected from the group consisting of halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6- alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, Ci-C6-alkoxy, Ci-C6-halo- genalkoxy and OR Y .
- R 4 is halogen, in particular F, CI, Br or 1, more specifically F, CI or Br, in particular • F or CI.
- R 4 is F.
- R 4 is CI.
- R 4 is Br.
- R 4 is OH.
- R 4 is CN.
- R 4 is N0 2 .
- R 4 is SH.
- R 4 is NH 2 .
- R 4 is , NH(Ci-C 4 -alkyl), in particular NH(CH 3 ), NH(C 2 H 5 ).
- R 4 is , N(Ci-C 4 -alkyl) 2 , in particular NH(CH 3 ) 2 , NH(C 2 H 5 ) 2 .
- R 4 is , NH(C 2 -C 4 -alkynyl), in particular NH(C ⁇ CH), NH(CH 2 C ⁇ CH).
- R 4 is , NH(C 3 -C6-cycloalkyl), in particular NH(C 3 H 7 ), NH(C 4 H 9 ).
- R 4 is , N(C 3 -C6-cycloalkyl)2, in particular N(C 3 H 7 ) 2 , N(C 4 H 9 ) 2 .
- R 4 is N(Ci-C4-alkyl)(C 2 -C4-alkynyl), in particular N(CH 3 )(C ⁇ CH), N(CH 3 )(CH 2 C ⁇ CH), N(C 2 H 5 )(C ⁇ CH), N(C 2 H 5 )(CH 2 C ⁇ CH).
- R 4 is N(Ci-C4-alkyl)(C 3 -C6-cycloalkyl), in particular N(CH 3 )(C 3 H 7 ), N(CH 3 )(C 4 H 9 ), N(C 2 H 5 )(C 3 H 7 ), N(CH 3 )(C 4 H 9 ).
- R 4 is N(C 2 -C4-alkynyl)(C 3 -C6-cycloalkyl), in particular N(C ⁇ CH)(C 3 H 7 ), N(CH 2 C ⁇ CH)(C 4 H 9 ), N(C ⁇ CH)(C 3 H 7 ), N(CH 2 C ⁇ CH)(C 4 H 9 ).
- R 4 is NH-S0 2 -R x such as NH-S0 2 -CH 3 , NH-S0 2 -CH 2 -CH 3 , NH-S0 2 -CF 3 , NH-S0 2 -Ts.
- R 4 is S(0)n-C 2 -C6-alkenyl such as
- R 4 is Ci-C6-alkyl, in particular Ci-C4-alkyl, such as CH3. or C2H5, in particular CH3 or CH2CH3.
- R 4 is Ci-C6-halogenalkyl, in particular C1-C4- halogenalkyl, such as CF 3 , CCI 3 , FCH 2 , CICH 2 , F 2 CH, CI 2 CH, CF3CH2, CCI3CH2 or CF 2 CHF 2 .
- R 4 is C2-C6-alkynyl or C2-C6-halogen- alkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as C CH, CH2 C CH, C CCI, CH 2 C ⁇ CCI, or CCI 2 C ⁇ CCI.
- R 4 is OR Y , wherein R Y is Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl.
- R 4 is OR Y , wherein R Y is Ci-C6-alkyl, in particular Ci-C4-alkyl, more specifically Ci-C2-alkoxy. R 4 is such as OCH3 or OCH2CH3.
- R 4 is OR Y , wherein R Y is Ci-C6-halogen- alkyl, in particular Ci-C4-halogenalkyl, more specifically Ci-C2-halogenalkyl.
- R 4 is such as OCF3, OCHF2, OCH2F, OCCI3, OCHC or OCH2CI, in particular OCF 3 , OCHF 2 , OCCI 3 or OCHCI 2 .
- R 4 is OR Y , wherein R Y C2-C6-alkenyl, in particular C2-C4-alkenyl, more specifically Ci-C2-alkenyl.
- R 4 is OR Y , wherein R Y C2-C6-alkynyl, in particular C2-C6-alkynyl, in particular C2-C4-alkynyl, more specifically Ci-C2-alkynyl.
- R 4 is such as OC ⁇ CH, OC ⁇ CCI, OCH 2 C ⁇ CCI, or OCCI 2 C ⁇ CCI
- R 4 is OR Y , wherein R Y is C3-C6-cycloalkyl, in particular cyclopropyl.
- R 4 is OR Y , wherein R Y is C3-C6-halogencyclo- alkyl.
- R 1 is fully or partially halogenated cyclopropyl.
- R 4 is is OR Y , wherein R Y C3-C6-cycloalkenyl, in particular cyclopropenyl.
- R 4 is C3-C6-cycloalkyl, in particular cyclopropyl.
- R 4 is C3-C6-halogencycloalkyl.
- R 4b is fully or partially halogenated cyclopropyl, such as 1 -F-cyclopropyl, 1 -CI- cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1 -Cl2-cyclopropyl
- R 4 is phenyl-Ci-C6-alkyl, such as phenyl- CH2, wherein the phenyl moiety in each case is unsubstituted or substituted with one, two or three identical or different groups R 4b which independently of one another are selected from hal- ogen, Ci-C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl and Ci-C2-halogenalkoxy, in particular F, CI, Br, CH 3 , OCH3, CF 3 and OCF 3 .
- R 4 is aryl, in particular phenyl, wherein the aryl or phenyl moiety in each case is unsubstituted or substituted with identical or different groups R 4b which independently of one another are selected from CN, halogen, Ci-C2-alkyl, Ci- C2-alkoxy, Ci-C2-halogenalkyl and Ci-C2-halogenalkoxy, in particular CN, F, CI, Br, CH3, OCH3, CHF2, OCHF2, CF3 and OCF3.
- R 4 is unsubstituted phenyl.
- R 4 is phenyl, that is substituted with one, two or three, in particular one, halogen, in particular selected from F, CI and Br, more specifically selected from F and CI.
- R 4 is a 5-membered heteroaryl such as pyr- rol-1 -yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1 -yl, pyrazol- 3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1 -yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2- yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, is
- R 3 is a 6-membered heteroaryl such as pyri- din-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, py- rimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl.
- R 4 is in each case independently selected from H, halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6- alkoxy, Ci-C6-halogenalkoxy,C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyl and C3-C6- halogencycloalkyl, wherein the acyclic moieties of R 4 are unsubstituted or substituted with identical or different groups R 4a as defined and preferably defined herein, and wherein the carbocy- die, phenyl and heteroaryl moieties of R 4 are unsubstituted or substituted with identical or different groups R 4b as defined and preferably defined herein.
- R 4 is in each case independently selected from H, halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6- alkoxy, Ci-C6-halogenalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyl and C3-C6- halogencycloalkyl, wherein the acyclic moieties of R 4 are unsubstituted or substituted with iden- tical or different groups R 4a as defined and preferably defined herein, and wherein the cycloalkyi moieties of R 4 are unsubstituted or substituted with identical or different groups R 4b as defined and preferably defined herein.
- R 4a are the possible substituents for the acyclic moieties of R 3 .
- R 4a is independently selected from halogen, OH, CN, C1-C6- alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, aryl and phenoxy, wherein the aryl and phenyl group is unsubstituted or substituted with substituents R 41a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy.
- R 4a is independently selected from halogen, Ci-C6-alkoxy, C3-C6- cycloalkyi, C3-C6-halogencycloalkyl and Ci-C4-halogenalkoxy.
- R 4a is independently selected from F, CI, Br, I, Ci-C2-alkoxy, cyclopropyl, 1 -F-cyclopropyl, 1-CI-cyclopropyl, 1 , 1 -F2- cyclopropyl, 1 ,1 -Cl2-cyclopropyl and Ci-C2-halogenalkoxy.
- R 4a is independently halogen, in particular selected from F, CI, Br and I, more specifically F, CI and Br.
- R 4b are the possible substituents for the carbocyclic, heteroaryl and phenyl moieties of R 4 .
- R 4b according to the invention is independently selected from halogen, OH, CN, Ci-C4-alkyl, C1-C4- alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and d-Ce-alkylthio.
- R 4b is independently selected from halogen, CN, C1-C4- alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl and Ci-C4-halogenalkoxy, in particular halogen, C1-C4- alkyl and Ci-C4-alkoxy.
- R 4b is independently selected from F, CI, CN, CH3, OCH3 and halogenmethoxy.
- R 4 Particularly preferred embodiments of R 4 according to the invention are in Table P4 below, wherein each line of lines P4-1 to P4-42 corresponds to one particular embodiment of the inven- tion, wherein P4-1 to P4-42 are also in any combination with one another a preferred embodiment of the present invention.
- the connection point to the carbon atom, to which R 4 is bound is marked with "#" in the drawings.
- R N is the substituent of the heteroatom N that is contained in the heterocycle formed by R 3 and R 4 in some of the inventive compounds.
- R N is selected from Ci-C4-alkyl, Ci-C4-halogenalkyl and S02Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted with one, two or three substituents selected from Ci-C4-alkyl.
- R N is in each case independently selected from Ci-C2-alkyl, Ci-C2-halogenalkyl and S02Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted with one methyl substituents.
- R N is in each case independently selected from Ci-C2-alkyl, more particularly methyl. In one particular embodiment, R N is in each case independently selected from S02Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted with one methyl.
- R 3 and R 4 together with the carbon atoms to which they are bound form a saturated or partially unsaturated five-, six-or seven -membered carbo- and heterocycle that is unsubstituted or substituted.
- R 3 and R 4 form a 3-membered saturated carbocycle.
- the carbocycle is unsubstituted, i.e. it does not carry any substituent R 34 .
- it is substituted with R 34 .
- R 3 and R 4 form a 4-membered saturated carbocycle.
- the carbocycle is unsubstituted, i.e. it does not carry any substituent R 34 .
- R 34 is substituted with R 34 .
- R 3 and R 4 form a 5-membered saturated carbocycle.
- the carbocycle is unsubstituted, i.e. it does not carry any substituent R 34 .
- R 34 is substituted with R 34 .
- R 3 and R 4 form a 6-membered saturated carbocycle.
- the carbocycle is unsubstituted, i.e. it does not carry any substituent R 34 .
- R 34 is substituted with R 34 .
- R 3 and R 4 form a 7-membered saturated carbocycle.
- the carbocycle is unsubstituted, i.e. it does not carry any substituent R 34 .
- R 34 is substituted with R 34 .
- R 3 and R 4 form a 3-membered saturated heterocycle.
- the carbocycle is unsubstituted, i.e. it does not carry any substituent R 34 .
- R 34 is substituted with R 34 .
- R 3 and R 4 form a 4-membered saturated heterocycle.
- the carbocycle is unsubstituted, i.e. it does not carry any substituent R 34 .
- R 34 is substituted with R 34 .
- R 3 and R 4 form a 5-membered saturated heterocycle.
- the carbocycle is unsubstituted, i.e. it does not carry any substituent R 34 .
- R 34 it is substituted with R 34 .
- R 3 and R 4 form a 6-membered saturated heterocycle.
- the carbocycle is unsubstituted, i.e. it does not carry any substituent R 34 .
- R 34 is substituted with R 34 .
- R 3 and R 4 form a 7-membered saturated heterocycle.
- the carbocycle is unsubstituted, i.e. it does not carry any substituent R 34 .
- R 34 is substituted with R 34 .
- R 3 and R 4 form a 5-membered saturated heteroaryl.
- the heteroaryl is unsubstituted, i.e. it does not carry any substituent R 34 .
- R 34 is substituted with R 34 .
- R 3 and R 4 form a 6-membered heteroaryl.
- the heteroaryl is unsubstituted, i.e. it does not carry any substituent R 34 .
- R 34 is substituted with R 34 .
- R x is as defined above;
- R 34 wherein the acyclic moieties of R 34 are unsubstituted or substituted with identical or different groups R 34a which independently of one another are selected from:
- R 34a halogen, OH, CN, Ci-C 6 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -halogencycloalkyl, Ci-C 4 -halo- genalkoxy, Ci-C6-alkylthio, aryl and phenoxy, wherein the aryl group is unsubstituted or unsubstituted or substituted with R 341a selected from the group consisting of halogen, OH, Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl, Ci-C 4 -alkoxy, Ci-C 4 -halogenalkoxy, CN, C3-C6-cycloalkyl, C 3 -C6-halogency- cloalkyl, Ci-C 4 -alkylthio;
- R 34 wherein the carbocyclic, heterocyclic, heteroaryl and aryl of R 34 are unsubstituted or substituted with identical or different groups R 34b which independently of one another are selected from:
- R 34b halogen, OH, CN, Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C 4 -halogenalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 - halogencycloalkyl, Ci-C 4 -halogenalkoxy and Ci-C6-alkylthio.
- m is 1.
- m is 2 or 3. According to one specific embodiment thereof, m is 2. According to still another embodiment of formula I, m is 3.
- R 34 is halogen, Ci-C6-alkyl, Ci-C6-halogenalkyl, Ci- Ce-alkoxy or , Ci-C 6 -halogenalkoxy, in particular CH 3 , Et, CHF 2 , OCH 3 , OCHF 2 , OCF 3 , F, CI, more specifically H, CH 3 , F or CI most preferred F or CI.
- R 34 is halogen, in particular Br, F or CI, more specifically F or CI.
- R 34 is OH.
- R 34 is CN.
- R 34 is NH2, NH(Ci-C 4 -alkyl), N(Ci-C 4 -alkyl)2 or NH-S02-R X , wherein R x is Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl, unsubstituted aryl or aryl that is substituted with one, two, three, four or five substituents R x34 independently selected from C1-C4- alkyl.
- R 34 is Ci-C6-alkyl, in particular Ci-C 4 -alkyl, such as CH 3 .
- R 34 is Ci-C6-halogenalkyl, in particular C1-C4- halogenalkyl, such as CF 3 , CHF 2 , CH 2 F, CCI 3 , CHCI2 or CH 2 CI.
- R 34 is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C 2 -C 4 -alkynyl or C 2 -C 4 -halogenalkynyl, such as C ⁇ CH, CH 2 C ⁇ CH, C ⁇ C-CI, C ⁇ C- CH 3 , CH 2 C ⁇ CH, CH 2 C ⁇ CCI or CH 2 C ⁇ C-CH 3 .
- R 34 is Ci-C6-alkoxy, in particular Ci-C 4 - alkoxy, more specifically Ci-C2-alkoxy such as OCH3 or OCH2CH3.
- R 34 is Ci-C6-halogenalkoxy, in particular Ci- C 4 -halogenalkoxy, more specifically Ci-C2-halogenalkoxy such as OCF3, OCHF2, OCH2F, OCCIs, OCHC or OCH2CI, in particular OCF 3 , OCHF 2 , OCCI 3 or OCHCI 2 .
- R 34 is C3-C6-cycloalkyl, in particular cyclopro- pyl.
- R 34 is C3-C6-cycloalkyl, for example cyclopro- pyl, substituted with one, two, three or up to the maximum possible number of identical or different groups R 34b as defined and preferably herein.
- R 34 is C3-C6-halogencycloalkyl.
- R 34 is fully or partially halogenated cyclopropyl.
- R 34 is unsubstituted aryl or aryl that is substituted with one, two, three or four R 34b , as defined herein.
- R 34 is unsubstituted phenyl or phenyl that is substituted with one, two, three or four R 34b , as defined herein.
- R 34 is unsubstituted 5- or 6-membered heteroaryl. According to still a further embodiment, R 34 is 5- or 6-membered heteroaryl that is substituted with one, two or three R 34b , as defined herein.
- R 34 is in each case independently selected from halogen, OH, CN, N0 2 , SH, NH 2 , NH(Ci-C 4 -alkyl), N(Ci-C 4 -alkyl) 2 , NH-S0 2 -R x , Ci-C 6 -alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy and C3-C6-cycloalkyl; wherein the acyclic moieties of R 34 are not further substituted or carry one, two, three, four or five identical or different groups R 34a as defined below and wherein the carbocyclic, heterocyclic and heteroaryl moieties of R 34 are not further substituted or carry one, two, three, four or five identical or different groups R 34b as defined below.
- R 34 is independently selected from halogen, OH, Ci-C6-alkyl, Ci-C6-halogenalkyl, Ci-C6-alkoxy and Ci-C6-halogenalkoxy, in particular independently selected from F, CI, Br, CN, OH, Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl, Ci-C 4 -alkoxy and Ci-C 4 -halogenalkoxy.
- R 34a are the possible substituents for the acyclic moieties of R 34 .
- R 34a is independently selected from halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, aryl and phe- noxy, wherein the aryl and phenyl group is unsubstituted or unsubstituted or substituted with R 341a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, C1-C4- alkoxy, Ci-C4-halogenalkoxy, CN, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-alkylthio.
- R 34a is independently selected from halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, aryl and phe- noxy, wherein the aryl and phenyl group is unsubstituted or unsubstituted or substituted with R 341a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, C1-C4- alkoxy and Ci-C4-halogenalkoxy, in particular selected from halogen, Ci-C2-alkyl, Ci-C2-halo- genalkyl, Ci-C2-alkoxy, Ci-C2-halogenalkoxy, more specifically selected from halogen, such as F, CI and Br.
- halogen such as F, CI and Br.
- R 34a is independently selected from halogen, OH, CN, Ci-C2-alkoxy, C3- C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C2-halogenalkoxy. Specifically, R 34a is
- R 34a is independently selected from halogen, such as F, CI, Br and I, more specifically F, CI and Br.
- R 34a is independently selected from OH, C3- C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C2-halogenalkoxy. Specifically, R 34a is
- R 34b are the possible substituents for the carbocyclic, heterocyclic and heteroaryl moieties of R 34 .
- R 34b according to the invention is independently selected from halogen, OH, CN, Ci-C4-alkyl, Ci- C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C4-halogen- alkoxy.
- R 34b is independently selected from halogen, CN, C1-C2- alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalky and Ci-C2-hal- ogenalkoxy.
- R 34b is independently selected from F, CI, OH, CN, CH3, OCH3, cyclopropyl, 1 -F-cyclopropyl, 1 -CI-cyclopropyl, 1 ,1-F2-cyclopropyl, 1 ,1 -Cl2-cyclopropyl and halogenmethoxy.
- R 34b is independently selected from Ci-C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C2-halogen- alkoxy.
- R 34b is independently selected from OH, CH3, OCH3, cyclopropyl, 1 -F- cyclopropyl, 1 -CI-cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1 -Cl2-cyclopropyl and halogenmethoxy, more specifically independently selected from OH, CH3, OCH3, cyclopropyl, 1 -F-cyclopropyl, 1 - Cl-cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1 -Cl2-cyclopropyl cyclopropyl and OCHF2.
- R 5 and R 6 together with the carbon atoms to whi Och they are bound together form a phenyl or five- or six-membered heteroaryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; and wherein the heteroaryl carries zero, one, two, three or four substituents (R 56 ) 0 , wherein o is 0, 1 , 2 or 3; and
- R 56 are independently selected from halogen, OH, CN, N0 2 , SH, NH 2 , NH(Ci-C 4 -alkyl),
- R 56 wherein the acyclic moieties of R 56 are not further substituted or carry one, two, three or up to the maximum possible number of identical or different groups R 56a which independently of one another are selected from:
- R 56a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6-halogencyclo- alkyl, C3-C6-halogencycloalkenyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, five- or six-membered heteroaryl, phenyl and phenoxy, wherein the heteroaryl and phenyl group is unsubstituted or carries one, two, three, four or five substituents R 56a' selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
- R 56 wherein the carbocyclic, phenyl, heterocyclic and heteroaryl moieties of R 56 are not further substituted or carry one, two, three, four, five or up to the maximum number of identical or different groups R 56b which independently of one another are selected from:
- R 56b halogen, OH, CN, Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C 4 -halogenalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 - halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio.
- R 5 and R 6 together with the carbon atoms to which they are bound form phenyl; wherein the phenyl carries zero, one or two substituents (R 56 ) 0 , as defined and preferably defined herein, wherein o is 0, 1 or 2. According to one specific embodiment, o is 0. According to a further embodiment, o is 1 or 2. Particular embodiments thereof are listed in Table P56.
- R 5 and R 6 together with the carbon atoms to which they are bound form a five- or six-membered heteroaryl; wherein the heteroaryl contains one or two heteroatoms selected from N, O and S, and wherein the heteroaryl carries zero, one or two substit- uents (R 56 ) 0 , as defined and preferably defined herein, wherein o is 0, 1 or 2. According to one specific embodiment, o is 0. According to a further embodiment, o is 1 or 2. Particular embodiments thereof are listed in Table P56.
- R 5 and R 6 together with the carbon atoms to which they are bound form a five- or six-membered heteroaryl; wherein the heteroaryl contains one or two heteroatoms N, and wherein the heteroaryl carries zero, one or two substituents (R 56 ) 0 , as defined and preferably defined herein, wherein o is 0, 1 or 2. According to one specific embodiment, o is 0. According to a further embodiment, o is 1 or 2. Particular embodiments thereof are listed in Table P56.
- R 5 and R 6 together with the carbon atoms to which they are bound form a five- or six-membered heteroaryl; wherein the heteroaryl contains one or two heteroatoms selected from S and O, and wherein the heteroaryl carries zero, one or two substituents (R 56 ) 0 , as defined and preferably defined herein, wherein o is 0, 1 or 2. According to one specific embodiment, o is 0. According to a further embodiment, o is 1 or 2. Particular embodiments thereof are listed in Table P56.
- R 5 and R 6 together with the carbon atoms to which they are bound form a five- or six-membered heteroaryl; wherein the heteroaryl contains one heteroatom S, and wherein the heteroaryl carries zero, one or two substituents (R 56 ) 0 , as defined and preferably defined herein, wherein o is 0, 1 or 2. According to one specific embodiment, o is 0. According to a further embodiment, o is 1 or 2. Particular embodiments thereof are listed in Table P56.
- R 5 and R 6 together with the carbon atoms to which they are bound form a five- or six-membered heteroaryl; wherein the heteroaryl contains one heteroatom O, and wherein the heteroaryl carries zero, one or two substituents (R 56 ) 0 , as defined and preferably defined herein, wherein o is 0, 1 or 2. According to one specific embodiment, o is 0. According to a further embodiment, o is 1 or 2. Particular embodiments thereof are listed in Table P56.
- R 5 and R 6 together with the carbon atoms to which they are bound form a five-membered heteroaryl; wherein the heteroaryl contains one or two
- heteroatoms selected from N, O and S, and wherein the heteroaryl carries zero, one or two substituents (R 56 ) 0 , as defined and preferably defined herein, wherein o is 0, 1 or 2. According to one specific embodiment, o is 0. According to a further embodiment, o is 1 or 2. Particular embodiments thereof are listed in Table P56.
- R 5 and R 6 together with the carbon atoms to which they are bound form a five-membered heteroaryl; wherein the heteroaryl contains one or two
- heteroaryl carries zero, one or two substituents (R 56 ) 0 , as defined and preferably defined herein, wherein o is 0, 1 or 2. According to one specific embodiment, o is 0. According to a further embodiment, o is 1 or 2. Particular embodiments thereof are listed in Table P56.
- R 5 and R 6 together with the carbon atoms to which they are bound form a five-membered heteroaryl; wherein the heteroaryl contains one or two
- heteroatoms selected from O and S and wherein the heteroaryl carries zero, one or two substituents (R 56 ) 0 , as defined and preferably defined herein, wherein o is 0, 1 or 2. According to one specific embodiment, o is 0. According to a further embodiment, o is 1 or 2. Particular embodiments thereof are listed in Table P56.
- R 5 and R 6 together with the carbon atoms to which they are bound form a five-membered heteroaryl; wherein the heteroaryl contains one heteroatom S, and wherein the heteroaryl carries zero, one or two substituents (R 56 ) 0 , as defined and preferably defined herein, wherein o is 0, 1 or 2. According to one specific embodiment, o is 0. According to a further embodiment, o is 1 or 2.
- R 5 and R 6 together with the carbon atoms to which they are bound form a five-membered heteroaryl; wherein the heteroaryl contains one heteroatom O, and wherein the heteroaryl carries zero, one or two substituents (R 56 ) 0 , as defined and preferably defined herein, wherein o is 0, 1 or 2. According to one specific embodiment, o is 0. According to a further embodiment, o is 1 or 2. Particular embodiments thereof are listed in Table P56.
- R 5 and R 6 together with the carbon atoms to which they are bound form a six-membered heteroaryl; wherein the heteroaryl contains one or two heteroatoms selected from N, O and S, and wherein the heteroaryl carries zero, one or two substituents (R 56 )o, as defined and preferably defined herein, wherein o is 0, 1 or 2. According to one specific embodiment, o is 0. According to a further embodiment, o is 1 or 2. Particular embodiments thereof are listed in Table P56.
- R 5 and R 6 together with the carbon atoms to which they are bound form a six-membered heteroaryl; wherein the heteroaryl contains one or two heteroatoms N, and wherein the heteroaryl carries zero, one or two substituents (R 56 ) 0 , as defined and preferably defined herein, wherein o is 0, 1 or 2. According to one specific embodiment, o is 0. According to a further embodiment, o is 1 or 2. Particular embodiments thereof are listed in Table P56.
- R 56 there can be zero, one, two or three R 56 present, namely for o is 0, 1 , 2 or 3.
- o 0.
- o is 1.
- o is 2 or 3. According to one specific embodiment thereof, o is 2, according to a further specific embodiment, o is 3.
- R 56 is halogen, in particular F, CI, Br or I, more specifically F, CI or Br, in particular F or CI.
- R 56 is F.
- R 56 is CI.
- R 56 is Br.
- R 56 is OH.
- R 56 is CN.
- R 56 is NO2.
- R 56 is SH.
- R 56 is NH2.
- R 56 is , NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, ,
- Ci-C 4 -alkyl is CH 3 , C 2 H 5 , n-propyl, i-pro- pyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
- R 56 is NH-S02-R X such as NH-SO2-CH3, NH-SO2-CH2-CH3, NH-SO2-CF3 or NH-SO2-TS.
- R 56 is Ci-C6-alkyl, in particular Ci-C4-alkyl, such as CH 3 , C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl., in particular CH 3 .
- R 56 is Ci-C6-halogenalkyl, in particular C1-C4- halogenalkyl, such as CF 3 , CCI 3 , FCH 2 , CICH 2 , F 2 CH, CI 2 CH, CF 3 CH 2 , CCI 3 CH 2 or CF 2 CHF 2 .
- R 56 is C 3 -C6-cycloalkyl, in particular cyclopro- pyl.
- R 56 is C 3 -C6-halogencycloalkyl.
- R 1 is fully or partially halogenated cyclopropyl.
- R 56 is C 2 -C6-alkynyl, in particular C 2 -C4-alkynyl, more specifically C 2 -C 3 -alkynyl, such as C ⁇ CH.
- R 56 is C 2 -C6-halogenalkynyl, in particular C 2 -C4-halogen- alkynyl, more specifically C 2 -C 3 -halogenalkynyl.
- R 56 is Ci-C6-alkoxy, in particular Ci-C4-alkoxy, more specifically Ci-C 2 -alkoxy such as OCH 3 or OCH 2 CH 3 .
- R 56 is Ci-C6-halogenalkoxy, in particular C1-C4- halogenalkoxy, more specifically Ci-C 2 -halogenalkoxy such as OCF 3 , OCHF 2 , OCH 2 F, OCCI 3 , OCHCI 2 , OCH 2 CI and OCF 2 CHF 2 , in particular OCF 3 , OCHF 2 and OCF 2 CHF 2 .
- R 56 is C 2 -C6-alkynyloxy, in particular C 2 - C4-alkynyloxy, more specifically Ci-C 2 -alkynyloxy such as OC CH
- R 56 is S(0) n -Ci-C6-alkyl, wherein alkyl is CH 3 , C 2 H 5 , n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl and n is 1 , 2 or 3.
- R 56 is S(0) n -Ci-C6-halogenalkyl, wherein halogenalkyl is CF 3 or CHF 2 and n is 1 , 2 or 3.
- R 56 is a partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered heterocycle, in particular three-, four-, five- or six-membered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the heterocycle is unsubstituted or substituted with substituents R 56b as defined below. According to one embodiment thereof, the heterocycle is unsubstituted.
- R 56 is a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered heterocycle, in particular three-, four-, five- or six-mem- bered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the heterocycle is unsubstituted or substituted with substituents R 56b as defined below. According to one embodiment thereof, the heterocycle is unsubstituted.
- the heterocycle contains preferably one, two or three, more specifically one or two heteroatoms selected from N, O and S. More specifically, the hetereocycle contains one heteroatom selected from N, O and S. In particular, the heterocycle contains one or two, in particular one O.
- R 56 is a 4-membered saturated heterocycle which contains 1 or 2 heteroatoms, in particular 1 heteroatom, from the group consisting of N, O and S, as ring members.
- the heterocycle contains one O as heteroatom.
- the formed heterocycle is oxetane.
- the heterocycle is unsubstituted, i.e. it does not carry any substituent R 56b . According to still another embodiment of formula I, it is substituted with R 56b .
- R 56 is a 5-membered saturated heterocycle which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S, as ring members.
- the heterocycle contains one O as heteroatom.
- the heterocycle is unsubstituted, i.e. it does not carry any substituent R 56b .
- it is substituted with R 56 .
- R 56 is a 6-membered saturated heterocycle which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S as ring members.
- the heterocycle is unsubstituted, i.e. it does not carry any substituent R 56b .
- R 56b it is substituted with R 56b .
- said 6-membered saturated heterocycle contains 1 or 2, in particular 1 , heteroatom(s) O. According to one
- the respective 6-membered heterocycle is unsubstituted, i.e. it does not carry any substituent R 56b . According to still another embodiment of formula I, it is substituted with R 56 .
- R 56 is phenyl-Ci-C6-alkyl, such as phenyl- CH2, wherein the phenyl moiety in each case is unsubstituted or substituted with one, two or three identical or different groups R 56b which independently of one another are selected from halogen, Ci-C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl and Ci-C2-halogenalkoxy, in particular CN, F, CI, Br, CH 3 , OCH 3 , CHF 2 , CF 3 OCHF 2 , and OCF 3 .
- R 56 is unsubstituted phenyl or phenyl that is substituted with one, two, three or four R 56b , as defined and preferably herein.
- R 56 is unsubstituted phenyl or phenyl that is substituted with one, two, three or four R 56b , as defined herein.
- R 56 is unsubstituted phenyl.
- R 56 is a 5-membered heteroaryl such as pyrrol-1 -yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1 -yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1 -yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isoxa
- R 56 is a 6-membered heteroaryl, such as pyr- idin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, py- rimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl.
- R 56 is in each case independently selected from halogen, CN, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyl, S(0) n -Ci-C6-alkyl, three-, four-, five- or six-membered saturated or partially unsaturated heterocycle, five- or six-membered heteroaryl and phenyl; wherein the heterocycle or heteroaryl contains one, two or three heteroatoms selected from N, O and S; and wherein the acyclic moieties of R 56 are not further substituted or carry one, two, three or up to the maximum possible number of identical or different groups R 56a as defined and preferably defined herein, and wherein the heterocyclic, alicyclic, phenyl and heteroaryl moieties of
- R 56 is in each case independently selected from halogen, CN, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, C3-C6- alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyl, S(0) n -Ci-C6-alkyl, three-, four-, five- or six-membered saturated or partially unsaturated heterocycle, five- or six-membered heteroaryl and phe- nyl; wherein the heterocycle or heteroaryl contains one, two or three heteroatoms selected from N, O and S; and wherein the acyclic moieties of R 56 are not further substituted or carry one, two, three or up to the maximum possible number of identical or different groups R 56a as defined and preferably defined herein, and wherein the heterocyclic, alipha-N-but
- the acyclic and cyclic moieties of R 56 are not further substituted, according to another embodiment, the acyclic moieties of R 56 carry one, two, three or four identical or different groups R 56a as defined and preferably defined herein.
- R 56 is in each case independently selected from halogen, CN, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyl and S(0) n -Ci-C6-alkyl, wherein the acyclic moieties of R 56 are not further substituted or carry one, two, three or up to the maximum possible number of identical or different groups R 56a as defined and preferably defined herein, and wherein the cycloalkyi moieties of R 56 are not further substituted or carry one, two, three, four, five or up to the maximum number of identical or different groups R 56b as defined and preferably defined herein.
- R 56 is in each case independently selected from halogen, CN, Ci-C6-alkyl, , Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, Ci-C6-halo- genalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyl and S(0) n -Ci-C6-alkyl, wherein the acyclic moieties of R 56 are not further substituted or carry one, two, three or up to the maximum possible number of identical or different groups R 56a as defined and preferably defined herein, and wherein the cycloalkyl moieties of R 56 are not further substituted or carry one, two, three, four, five or up to the maximum number of identical or different groups R 56b as defined and preferably defined herein.
- the acyclic and cyclic moieties of R 56 are not further substituted, according to another embodiment, the acyclic moieties of R 56 carry one, two, three or four identical or different groups R 56a as defined and preferably defined herein.
- R 56 is in each case independently selected from halo- gen, Ci-C6-alkyl and Ci-C6-alkoxy, wherein the acyclic moieties of R 56 are not further substituted or carry one, two, three or up to the maximum possible number of identical or different groups R 56a defined and preferably defined herein.
- R 56 is in each case independently selected from CN, halogen, Ci-C6-alkyl, Ci-C6-halogenalkyl, Ci-C6-alkoxy and Ci-C6-halogenalkoxy, wherein the acyclic moieties of R 56 are not further substituted or carry one, two, three or up to the maximum possible number of identical or different groups R 56a defined and preferably defined herein. Accordingto one specific embodiment, the acyclic and cyclic moieties of R 56 are not further substituted, according to another embodiment, the acyclic moieties of R 56 carry one, two, three or four identical or different groups R 56a as defined and preferably defined herein.
- R 56a are the possible substituents for the acyclic moieties of R 56 .
- R 56a is independently selected from halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6- halogencycloalkyl, C3-C6-halogencycloalkenyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, five- or six- membered heteroaryl, phenyl and phenoxy, wherein the heteroaryl and phenyl group is unsubstituted or carries one, two, three, four or five substituents R 56a' selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and C1-C4- halogenalkoxy.
- R 56a is independently selected from halogen, Ci-C6-alkoxy, C3- C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C4-halogenalkoxy. Specifically, R 56a is
- R 56a is independently halogen, in particular selected from F, CI, Br and I, more specifically F, CI and Br.
- R 56b are the possible substituents for the cycloalkyl, heterocyclyl, heteroaryl and phenyl moieties of R 56 .
- R 56b according to the invention is independently selected from halogen, OH, CN, C1-C4- alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4- halogenalkoxy and Ci-C6-alkylthio.
- R 56b is independently selected from halogen, CN, C1-C4- alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl and Ci-C4-halogenalkoxy, in particular halogen, C1-C4- alkyl and Ci-C4-alkoxy.
- R 56b is independently selected from F, CI, CN, CH 3 , OCH 3 and halogenmethoxy.
- R 5 and R 6 optionally substituted with (R 56 ) 0 , according to the invention are in Table P56 below, wherein each line of lines P56-1 to P56-82 corresponds to one particular embodiment of the invention, wherein P56-1 to P56-82 are also in any combination with one another a preferred embodiment of the present invention.
- the positions of the heteroaryls marked with "#" represents the connection points (carbon atoms 5' and 6' in formula I) with the remaining skeleton of the compounds of formula I:
- A is according to one embodiment O.
- A is according to one further embodiment S.
- B is according to one embodiment is -C(R 7 R 8 )-S-.
- B is according to one further embodiment C(R 7 R 8 )-S(0)-.
- B is according to one further embodiment C(R 7 R 8 )-S(0)2-.
- B is according to one further embodiment -C(R 7 R 8 )-0-.
- B is according to one further embodiment -C(R 7 R 8 )-NR 9 -.
- R x is as defined above;
- R 7 wherein the acyclic moieties of R 7 are independently not further substituted or carry one, two, three or up to the maximum possible number of identical or different groups R 7a , which independently of one another are selected from:
- R 7 wherein the carbocclic, heterocyclic, heteroaryl and aryl moieties of R 7 are independently unsubstituted or substituted with identical or different groups R 7b , which independently of one an- other are selected from:
- R 7 is selected from Ci-C6-alkyl, Ci-C6-halo- genalkyl, CN , C 2 -C6-alkenyl, C 2 -C6-halogenalkenyl, C 2 -C6-alkynyl, C 2 -C6-halogenalkynyl, C3-C6- cycloalkyl, C3-C6-halogencycloalkyl, Ci-C6-alkylaryl, Ci-C6-alkylheteroaryl, phenyl, pyridine, py- rimidine, thiophene, imidazole, triazol, oxadiazol wherein the acyclic moieties of R 7 are unsubstituted or substituted with identical or different groups R 7a as defined below and wherein wherein the carbocycle, heterocycle, heteroaryl and aryl moieties are unsubstituted or substituted with substituents R
- R 7 is H.
- R 7 is F
- R 7 is CI
- R 7 is Br.
- R 7 is OH.
- R 7 is CN
- R 7 is NO2.
- R 7 is SH.
- R 7 is Ci-C6-alkylthio, such as SCH3, SC2H5, Sn-propyl, Si-propyl, Sn-butyl, Si-butyl, Stert-butyl, Sn-pentyl, Si-pentyl, CH2SCH3 or
- R 7 is Ci-C6-halogenalkylthio, such as SCF3, SCCI3, CH2SCF3 or CH2SCF3.
- R 7 is selected from Ci-C6-alkyl, Ci-C6-halo- genalkyl, phenyl, halogenphenyl and three-, four-, five- or six-membered carbo- and heterocycle, wherein the carbo- and heterocycle is unsubstituted or is substituted with substituents R 7b as defined below. According to one embodiment thereof, the carbocycle is unsubstituted.
- R 7 is selected from Ci-C6-halogenalkyl, phenyl-Chb, halogenphenyl- CH2, phenyl, halogenphenyl and three-, four-, five- or six-membered carbo- and heterocycle, wherein the carbo- and heterocycle is unsubstituted or is substituted with substituents R 7b as defined below.
- R 7 is selected from Ci-C6-alkyl, Ci-C6-halo- genalkyl, phenyl, halogenphenyl and three-, four-, five- or six-membered carbo- and heterocycle, wherein the carbo- and heterocycle is unsubstituted or substituted withsubstituents R 7b as defined below. According to one embodiment thereof, the carbo- and heterocycle is unsubstituted.
- R 7 is selected from substituted Ci-C6-halogenalkyl, phenyl, halogenphenyl and three-, four-, five- or six-membered carbo- and heterocycle, wherein the carbo- and heterocycle is unsubstituted or substituted withsubstituents R 7b as defined below.
- R 7 is selected from Ci-C6-alkyl, Ci-C6-halogen- alkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloal- kyl, C3-C6-halogencycloalkyl, Ci-C6-alkylaryl, six-membered heteroaryl or aryl which is unsubstituted or substituted with halogen or Ci-C6-halogenalkyl, and wherein the acyclic moieties of R 7 are unsubstituted or substituted with identical or different groups R 7a as defined below and wherein wherein the carbocycle, heterocycle and heteroaryl and aryl moieties are unsubstituted or substituted with substituents R 7b as defined below.
- R 7 is selected from Ci-C6-alkyl, Ci-C6-halo- genalkyl, CN, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3-C6- cycloalkyl, C3-C6-halogencycloalkyl, Ci-C6-alkylaryl, phenyl, pyridine, pyrimidine, thiophene, im- idazole, triazol, oxadiazol wherein the acyclic moieties of R 7 are unsubstituted or substituted with identical or different groups R 7a as defined below and wherein wherein the carbocycle, heterocycle and heteroaryl and aryl moieties are unsubstituted or substituted with substituents R 7b as defined below.
- R 7 is Ci-C6-alkyl such as CH3, C2H5, n-pro- pyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
- R 7 is Ci-C6-alkyl such as CH3, C2H5, n-pro- pyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
- R 7 is Ci-C6-alkyl such as CH3.
- R 7 is Ci-C6-alkyl such as C2H5.
- R 7 is Ci-C6-alkyl such as CH3, C2H5, n-pro- pyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl which is substituted with at least one group R 7a , which independently of one another are selected from:
- R 7 is CH3 is substituted with at least one group R 7a , which independently of one another are selected from:
- R 7 is C2H5 is substituted with at least one group R 7a , which independently of one another are selected from:
- R 7 is CH2CN.
- R 7 is CH2OH.
- R 7 is Ci-C6-halogenalkyl, in particular C1-C4- halogenalkyl, more specifically Ci-C2-halogenalkyl, such as CF3, CC , FCH2, CICH2, F2CH, C CH, CF3CH2, CCI3CH2 or CF2CHF2.
- R 7 is CH2F.
- R 7 is CHF2.
- R 7 is CF3.
- R 7 is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as C CH, C C-CI, CH2- C ⁇ CH, CH 2 -C ⁇ CCI or CH 2 - C ⁇ C-CH 3 .
- R 7 is C2-C6-cycloalkynyl in particular C2-C4- cycloalkynyl, such as C C-cPr.
- R 7 is Ci-C6-alkoxy, in particular C1-C4- alkoxy, more specifically Ci-C2-alkoxy such as OCH3, CH2CH3 or CH2OCH3.
- R 7 is Ci-C6-alkyl-Ci-C6-alkoxy, in particular Ci-C4-alkyl-Ci-C4-alkoxy, more specifically Ci-C2-alkyl-Ci-C2-alkoxy, such as
- R 7 is C2-C6-alkynyloxy, in particular C2- C4-alkynyloxy, more specifically Ci-C2-alkynyloxy such as OC CH, OChbC CH or ChbOC CH
- R 7 is Ci-C6-halogenalkoxy, in particular Ci-C4-halogenalkoxy, more specifically Ci-C2-halogenalkoxy such as OCF3, OCHF2, OCH2F, OCCIs, OCHC or OCH2CI, in particular OCF 3 , OCHF 2 , OCCI 3 or OCHCI 2 .
- R 7 is Ci-C6-alkyl-Ci-C6-halogenalkoxy, in particular Ci-C4-alkyl-Ci-C4-halogenalkoxy, more specifically Ci-C2-alkyl-Ci-C2-halogenalkoxy such as CH2OCF3, CH2OCHF2, CH2OCH2F, CH2OCCI3, CH2OCHCI2 or CH2OCH2CI, in particular CH2OCF3, CH 2 OCHF 2 , CH2OCCI3 or CH2OCHCI2.
- alkyl is CH 3 , C 2 H 5 , n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
- R 7 is Ci-C6-alkyl-NH(Ci-C4-alkyl) or Ci- C6-alkyl-N(Ci-C 4 -alkyl)2, wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
- R 7 is Ci-C6-alkyl-S(0) n -Ci-C6-alkyl, wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl and n is 1 , 2 or 3.
- R 7 is Ci-C6-alkyl-S(0) n -Ci-C6- halogenalkyl, wherein halogenalkyl is CF3 or CHF2 and n is 1 , 2 or 3.
- R 7 is Ci-C6-alkyl-S(0) n -aryl, wherein the aryl or phenyl moiety in each case is unsubstituted or substituted with identical or different groups R 7b which independently of one another are selected from halogen, Ci-C2-alkyl, C1-C2- alkoxy, Ci-C2-halogenalkyl, Ci-C2-halogenalkoxy and S(0) n -Ci-C6-alkyl, in particular F, CI, Br, CH3, OCH3, CF3, CHF2, OCHF2, OCF3. According to one embodiment, R 7 is unsubstituted phenyl.
- R 7 is phenyl, that is substituted with one, two or three, in particular one, halogen, in particular selected from F, CI and Br, more specifically selected from F and CI.
- R 7 is Ci-C6-alkyl-NH-S02-R x wherein R x is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted with one, two, three, four or five substituents R x2 independently selected from Ci-C4-alkyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy, or Ci-C4-halogenalkoxy, such as CH2NHS02CF3 or
- R 7 is selected from Ci-C6-alkyl which is substituted, a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle, in particular three-, four-, five- or six-membered, wherein the carbocycle is unsubstituted or substituted with substituents R 7b as defined below.
- the car- bocycle is unsubstituted.
- R 7 is selected from Ci-C6-alkyl, especially CH2 which is substituted with a 3-membered saturated carbocycle.
- the carbocycle is unsubstituted, i.e. it does not carry any substituent R 7b .
- R 7b is substituted with R 7b .
- R 7 is selected from Ci-C6-alkyl, especially CH2 which is substituted with a 4-membered saturated carbocycle.
- the carbocycle is unsubstituted, i.e. it does not carry any substituent R 7b .
- R 7b is substituted with R 7b .
- R 7 is selected from Ci-C6-alkyl, especially with CH2 optionally substituted CH2 which is substituted with a 5-membered saturated carbocycle.
- the carbocycle is unsubstituted, i.e. it does not carry any substituent R 7b .
- R 7b is substituted with R 7b .
- R 7 is selected from Ci-C6-alkyl, especially CH2 which is substituted with a 6-membered saturated carbocycle.
- the carbocycle is unsubstituted, i.e. it does not carry any substituent R 7b .
- R 7b is substituted with R 7b .
- R 7 is Ci-C6-alkyl, especially CH2 substituted with a 4-membered saturated heterocyde which contains 1 or 2 heteroatoms, in particular 1 heteroatom, from the group consisting of N, O and S, as ring members.
- the heterocyde contains one O as heteroatom.
- the formed heterocyde is oxetane.
- the heterocyde is unsubstituted, i.e. it does not carry any substituent R 7b .
- it is substituted with R 7b .
- R 7 is Ci-C6-alkyl, especially CH2 substituted with a 5-membered saturated heterocyde which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S, as ring members.
- the heterocyde contains one O as heteroatom.
- the heterocyde is unsubstituted, i.e. it does not carry any substituent R 7b .
- it is substituted with R 7b .
- R 7 is Ci-C6-alkyl, especially CH2 subsitited by a 6-membered saturated heterocyde which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S as ring members.
- the heterocycle is unsubstituted, i.e. it does not carry any substituent R 7b .
- R 7b it is substituted with R 7b .
- said 6-membered saturated heterocycle contains 1 or 2, in particu- lar 1 , heteroatom(s) O.
- the respective 6-membered heterocycle is unsubstituted, i.e. it does not carry any substituent R 7b .
- it is substituted with R 7b .
- R 7 is a partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle, in particular three-, four-, five- or six-membered, wherein the carbocycle is unsubstituted or substituted with substituents R 7b as defined below. According to one embodiment thereof, the carbocycle is unsubstituted.
- R 7 is a partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, in particular three-, four-, five- or six-membered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the carbocycle and heterocycle are unsubstituted or substituted with substituents R 7b as defined below. According to one embodiment thereof, the carbocycle or heterocycle is unsubstituted.
- R 7 is a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, in particular three-, four-, five- or six-membered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the carbocycle and heterocycle are unsubstituted or substituted with substit- uents R 7b as defined below. According to one embodiment thereof, the carbocycle or heterocycle is unsubstituted.
- R 7 is a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle, in particular three-, four-, five- or six-membered, wherein the carbocycle is unsubstituted or substituted with substituents R 7b as defined below. According to one embodiment thereof, the carbocycle is unsubstituted.
- R 7 is a 3-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R 7b . According to still another embodiment of formula I, it is substituted with R 7b .
- R 7 is a 3-membered saturated carbocycle, which is
- R 7 is a 3-membered saturated carbocycle, which is substituted with halogen, more specifically by F, such as C3H3F2.
- R 7 is a 3-membered saturated carbocycle, which is substituted with halogen. More specifically by CI, such as C3H3CI2.
- R 7 is a 4-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R 7b . According to still another embodiment of formula I, it is substituted with R 7b .
- R 7 is a 5-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R 7b . According to still another embodiment of formula I, it is substituted with R 7b .
- R 7 is a 6-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R 7b . According to still another embodiment of formula I, it is substituted with R 7b .
- R 7 is a partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered heterocycle, in particular three-, four-, five- or six-membered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the heterocycle is unsubstituted or substituted with substituents R 7b as defined below. According to one embodiment thereof, the heterocycle is unsubstituted.
- R 7 is a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered heterocycle, in particular three-, four-, five- or six-mem- bered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the heterocycle is unsubstituted or substituted with substituents R 7b as defined below. According to one embodiment thereof, the heterocycle is unsubstituted.
- the heterocycle contains preferably one, two or three, more specifically one or two heteroatoms selected from N, O and S. More specifically, the hetereocycle contains one heteroatom selected from N, O and S. In particular, the heterocycle contains one or two, in particular one O.
- R 7 is a 4-membered saturated heterocycle which contains 1 or 2 heteroatoms, in particular 1 heteroatom, from the group consisting of N, O and S, as ring members.
- the heterocycle contains one O as heteroatom.
- the formed heterocycle is oxetane.
- the heterocycle is unsubstituted, i.e. it does not carry any substituent R 7b .
- it is substituted with R 7b .
- R 7 is a 5-membered saturated heterocycle which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S, as ring members.
- the heterocycle contains one O as heteroatom.
- the heterocycle is unsubstituted, i.e. it does not carry any substituent R 7b .
- it is substituted with R 7 .
- R 7 is a 6-membered saturated heterocycle which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S as ring members.
- the heterocycle is unsubstituted, i.e. it does not carry any substituent R 7b .
- it is substituted with R 7b .
- said 6-membered saturated heterocycle contains 1 or 2, in particular 1 , heteroatom(s) O.
- the respective 6-membered heterocycle is unsubstituted, i.e. it does not carry any substituent R 7b .
- R 7 is phenyl-Ci-C6-alkyl, such as phenyl- CH2, wherein the phenyl moiety in each case is unsubstituted or substituted with one, two or three identical or different groups R 7b which independently of one another are selected from CN, halogen, Ci-C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, Ci-C2-halogenalkoxy and S(0) n -Ci-C6- alkyl, in particular from CN, F, CI, Br, CH 3 , OCH 3 , CF 3 , CHF 2 , OCHF 2 , OCF 3 and S(0) 2 CH 3 .
- R 7 is aryl, in particular phenyl, wherein the aryl or phenyl moiety in each case is unsubstituted or substituted with identical or different groups R 7b which independently of one another are selected from from CN, halogen, Ci-C2-al- kyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, Ci-C2-halogenalkoxy and S(0) n -Ci-C6-alkyl, in particular from CN, F, CI, Br, CH 3 , OCH 3 , CF 3 , CHF 2 , OCHF 2 , OCF 3 .
- R 7 is unsubstituted phenyl.
- R 7 is phenyl, that is substituted with one, two or three, in particular one, halogen, in particular selected from F, CI and Br, more specifically selected from F and CI.
- R 7 is a 5-membered heteroaryl such as pyr- rol-1 -yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1 -yl, pyrazol- 3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1 -yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2- yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, is
- R 7 is a 6-membered heteroaryl, such as pyri- din-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, py- rimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl.
- R 7 Particularly preferred embodiments of R 7 according to the invention are in Table P7 below, wherein each line of lines P7-1 to P7-34 corresponds to one particular embodiment of the invention, wherein P7-1 to P7-34 are also in any combination with one another a preferred embodiment of the present invention.
- the connection point to the carbon atom, to which R 7 is bound is marked with "#" in the drawings.
- R x is as defined above;
- R 8 wherein the acyclic moieties of R 8 are independently not further substituted or carry one, two, three or up to the maximum possible number of identical or different groups R 8a , which independently of one another are selected from:
- alkyl 2 , NH-S0 2 -R x , Ci-C 6 -alkylthio, Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl, Ci-C 4 -alkoxy, Ci-C 4 -halo- genalkoxy, and S(0)n-Ci-C6-alkyl; and wherein R x , R' and R" are as defined above; n is 0, 1 , 2; and
- R 8 wherein the carbo-, heterocyclic, heteroaryl and phenyl moieties of R 8 are independently unsubstituted or substituted with identical or different groups R 8b , which independently of one another are selected from:
- R 8 is H.
- R 8 is F
- R 8 is CI
- R 8 is Br.
- R 8 is OH.
- R 8 is CN
- R 8 is NO2.
- R 8 is SH.
- R 8 is Ci-C6-alkylthio, such as SCH3, SC2H5, Sn-propyl, Si-propyl, Sn-butyl, Si-butyl, Stert-butyl, Sn-pentyl, Si-pentyl, CH2SCH3 or
- R 8 is Ci-C6-halogenalkylthio, such as SCF3, SCCI3, CH2SCF3 or CH2SCF3.
- R 8 is selected from Ci-C6-alkyl, Ci-C6-halo- genalkyl or Ci-C6-alkyl which is substituted, Ci-C6-halogenalkyl, phenyl, halogenphenyl and three-, four-, five- or six-membered carbo- and heterocycle, wherein the carbo- and heterocycle is unsubstituted or is substituted with substituents R 8b as defined below. According to one embodiment thereof, the carbocycle is unsubstituted.
- R 8 is selected from Ci-C6-halogenalkyl, phenyl-Chb, halogenphenyl-Chb, phenyl, halogenphenyl and three-, four-, five- or six-membered carbo- and heterocycle, wherein the carbo- and heterocycle is unsubstituted or is substituted with substituents R 8b as defined below.
- R 8 is selected from Ci-C6-alkyl, Ci-C6-halo- genalkyl or Ci-C6-alkyl which is substituted, Ci-C6-halogenalkyl, phenyl, halogenphenyl and three-, four-, five- or six-membered carbo- and heterocycle, wherein the carbo- and heterocycle is unsubstituted or substituted withsubstituents R 8b as defined below. According to one embodi- ment thereof, the carbo- and heterocycle is unsubstituted.
- R 8 is selected from substituted Ci-C6-halogenalkyl, phenyl, halogenphenyl and three-, four-, five- or six- membered carbo- and heterocycle, wherein the carbo- and heterocycle is unsubstituted or substituted withsubstituents R 8b as defined below.
- R 8 is selected from Ci-C6-alkyl, Ci-C6-halogen- alkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloal- kyl, C3-C6-halogencycloalkyl, Ci-C6-alkylaryl, six-membered heteroaryl or aryl which is unsubstituted or substituted with halogen or Ci-C6-halogenalkyl, and wherein the acyclic moieties of R 8 are unsubstituted or substituted with identical or different groups R 8a as defined below and wherein wherein the carbocycle, heterocycle and heteroaryl and aryl moieties are unsubstituted or substituted with substituents R 8b as defined below.
- R 8 is selected from Ci-C6-alkyl, Ci-C6-halo- genalkyl, CN, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3-C6- cycloalkyl, C3-C6-halogencycloalkyl, Ci-C6-alkylaryl, phenyl, pyridine, pyrimidine, thiophene, imidazole, triazol, oxadiazol wherein the acyclic moieties of R 8 are unsubstituted or substituted with identical or different groups R 8a as defined below and wherein wherein the carbocycle, heterocycle and heteroaryl and aryl moieties are unsubstituted or substituted with substituents R 8b as defined below.
- R 8 is Ci-C6-alkyl such as CH3, C2H5, n-pro- pyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
- R 8 is Ci-C6-alkyl such as CH3.
- R 8 is Ci-C6-alkyl such as C2H5.
- R 8 is Ci-C6-alkyl such as CH3, C2H5, n-pro- pyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl which is substituted with at least one group R 8a , which independently of one another are selected from:
- R 8 is C 2 H 5 is substituted with at least one group R 8a , which independently of one another are selected from:
- R 8 is CH 2 CN.
- R 8 is CH 2 OH.
- R 8 is Ci-C6-halogenalkyl, in particular Ci-C 4 - halogenalkyl, more specifically Ci-C 2 -halogenalkyl, such as CF3, CCI3, FCH 2 , CICH 2 , F 2 CH, CI 2 CH, CF 3 CH 2 , CCI 3 CH 2 or CF 2 CHF 2 .
- R 8 is CH 2 F.
- R 8 is CHF 2 .
- R 8 is CF3.
- R 8 is C2-C6-cycloalkynyl in particular C2-C4- cycloalkynyl, such as C C-cPr.
- R 8 is Ci-C6-alkoxy, in particular C1-C4- alkoxy, more specifically Ci-C2-alkoxy such as OCH3, CH2CH3 or CH2OCH3.
- R 8 is Ci-C6-alkyl-Ci-C6-alkoxy, in particular Ci-C4-alkyl-Ci-C4-alkoxy, more specifically Ci-C2-alkyl-Ci-C2-alkoxy, such as
- R 8 is C2-C6-alkynyloxy, in particular C2- C4-alkynyloxy, more specifically Ci-C2-alkynyloxy such as OC CH, OChbC CH or ChbOC CH
- R 8 is Ci-C6-halogenalkoxy, in particular Ci-C4-halogenalkoxy, more specifically Ci-C2-halogenalkoxy such as OCF3, OCHF2, OCH2F, OCCI3, OCHC or OCH2CI, in particular OCF 3 , OCHF 2 , OCCI 3 or OCHCI 2 .
- R 8 is Ci-C6-alkyl-Ci-C6-halogenalkoxy, in particular Ci-C4-alkyl-Ci-C4-halogenalkoxy, more specifically Ci-C2-alkyl-Ci-C2-halogenalkoxy such as CH2OCF3, CH2OCHF2, CH2OCH2F, CH2OCCI3, CH2OCHCI2 or CH2OCH2CI, in particular CH2OCF3, CH 2 OCHF 2 , CH2OCCI3 or CH2OCHCI2.
- R 8 is Ci-C6-alkyl-NH(Ci-C4-alkyl) orCi- C6-alkyl-N(Ci-C4-alkyl)2, wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
- R 8 is Ci-C6-alkylthio, in particular C1-C4- alkoxy, more specifically Ci-C3-alkylthio such as CH2SCH3 or CH2SCH2CH3.
- R 8 is Ci-C6-alkyl-S(0) n -Ci-C6-alkyl, wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl and n is 1 , 2 or 3.
- R 8 is Ci-C6-alkyl-S(0) n -Ci-C6- halogenalkyl, wherein halogenalkyl is CF3 or CHF2 and n is 1 , 2 or 3.
- R 8 is Ci-C6-alkyl-S(0) n -aryl, wherein the aryl or phenyl moiety in each case is unsubstituted or substituted with identical or different groups R 8b which independently of one another are selected from halogen, Ci-C2-alkyl, C1-C2- alkoxy, Ci-C2-halogenalkyl, Ci-C2-halogenalkoxy and S(0) n -Ci-C6-alkyl, in particular F, CI, Br, CH3, OCH3, CF3, CHF2, OCHF2, OCF3.
- R 8 is unsubstituted phenyl.
- R 8 is phenyl, that is substituted with one, two or three, in particular one, halogen, in particular selected from F, CI and Br, more specifically selected from F and CI.
- R 8 is Ci-C6-alkyl-NH-S02-R x wherein R x is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted with one, two, three, four or five substituents R x2 independently selected from Ci-C4-alkyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy, or Ci-C4-halogenalkoxy, such as ChbNHSC ⁇ CFs or
- R 8 is selected from Ci-C6-alkyl which is sub- stituted, a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle, in particular three-, four-, five- or six-membered, wherein the carbocycle is unsubstituted or substituted with substituents R 8b as defined below. According to one embodiment thereof, the carbocycle is unsubstituted.
- R 8 is selected from Ci-C6-alkyl, especially CH2 which is substi- tuted with a 3-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R 8b . According to still another embodiment of formula I, it is substituted with R 8b .
- R 8 is selected from Ci-C6-alkyl, especially CH2 which is substituted with a 4-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R 8b . According to still another embodiment of formula I, it is substituted with R 8b .
- R 8 is selected from Ci-C6-alkyl, especially CH2 which is substituted with a 5-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R 8b . According to still another embodiment of formula I, it is substituted with R 8b . According to one embodiment, R 8 is selected from Ci-C6-alkyl, especially Chb which is substituted with a 6-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R 8b . According to still another embodiment of formula I, it is substituted with R 8b .
- R 8 is Ci-C6-alkylheterocycle, especially CH2 substituted with a 4-membered saturated heterocyde which contains 1 or 2 heteroatoms, in particular 1 heteroatom, from the group consisting of N, O and S, as ring members.
- the heterocyde contains one O as heteroatom.
- the formed heterocyde is oxetane.
- the heterocyde is unsubstituted, i.e. it does not carry any substituent R 8b .
- it is substituted with R 8b .
- R 8 is Ci-C6-alkylheterocycle, especially CH2 substituted with a 5-membered saturated heterocyde which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S, as ring members.
- the heterocyde contains one O as heteroatom.
- the heterocyde is unsubstituted, i.e. it does not carry any substituent R 8b .
- it is substituted with R 8b .
- R 8 is Ci-C6-alkylheterocycle, especially CH2 subsitited by a 6-membered saturated heterocyde which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S as ring members.
- the heterocyde is unsubstituted, i.e. it does not carry any substituent R 8b .
- it is substituted with R 8b .
- said 6-membered saturated heterocyde contains 1 or 2, in particular 1 , heteroatom(s) O.
- the respective 6-membered heterocyde is unsubstituted, i.e. it does not carry any substituent R 8b .
- it is substituted with R 8b .
- R 8 is a partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle, in particular three-, four-, five- or six-membered, wherein the carbocycle is unsubstituted or substituted with substituents R 8b as defined below. According to one embodiment thereof, the carbocycle is unsubstituted.
- R 8 is a partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocyde, in particular three-, four-, five- or six-membered, wherein the heterocyde contains one, two, three or four heteroatoms selected from N, O and S, and wherein the carbocycle and heterocyde are unsubstituted or substituted with substituents R 8b as defined below. According to one embodiment thereof, the carbocycle or heterocyde is unsubstituted.
- R 8 is a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocyde, in particular three-, four-, five- or six-membered, wherein the heterocyde contains one, two, three or four heteroatoms selected from N, O and S, and wherein the carbocycle and heterocycle are unsubstituted or substituted with substit- uents R 8b as defined below. According to one embodiment thereof, the carbocycle or heterocycle is unsubstituted.
- R 8 is a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle, in particular three-, four-, five- or six-mem- bered, wherein the carbocycle is unsubstituted or substituted with substituents R 8b as defined below. According to one embodiment thereof, the carbocycle is unsubstituted.
- R 8 is a 3-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R 8b . According to still another embodiment of formula I, it is substituted with R 8b .
- R 8 is a 3-membered saturated carbocycle, which is
- R 8 is a 3-membered saturated carbocycle, which is substituted with halogen, more specifically by F, such as C3H3F2.
- R 8 is a 3-membered saturated carbocycle, which is substituted with halogen. More specifically by CI, such as C3H3CI2.
- R 8 is a 4-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R 8b . According to still another embodiment of formula I, it is substituted with R 8b .
- R 8 is a 5-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R 8b . According to still another embodiment of formula I, it is substituted with R 8b .
- R 8 is a 6-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R 8b . According to still another embodiment of formula I, it is substituted with R 8b .
- R 8 is a partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered heterocycle, in particular three-, four-, five- or six-membered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the heterocycle is unsubstituted or substituted with substituents R 8b as defined below. According to one embodiment thereof, the heterocycle is unsubstituted.
- R 8 is a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered heterocycle, in particular three-, four-, five- or six-membered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the heterocycle is unsubstituted or substituted with substituents R 8b as de- fined below. According to one embodiment thereof, the heterocycle is unsubstituted.
- the heterocycle contains preferably one, two or three, more specifically one or two heteroatoms selected from N, O and S. More specifically, the hetereocycle contains one heteroatom selected from N, O and S. In particular, the heterocycle contains one or two, in particular one O.
- R 8 is a 4-membered saturated heterocycle which contains 1 or 2 heteroatoms, in particular 1 heteroatom, from the group consisting of N, O and S, as ring members.
- the heterocycle contains one O as heteroatom.
- the formed heterocycle is oxetane.
- the heterocycle is unsubstituted, i.e. it does not carry any substituent R 8b .
- it is substituted with R 8b .
- R 8 is a 5-membered saturated heterocycle which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S, as ring members.
- the heterocycle contains one O as heteroa- torn.
- the heterocycle is unsubstituted, i.e. it does not carry any substituent R 8b .
- it is substituted with R 8b .
- R 8 is a 6-membered saturated heterocycle which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S as ring members.
- the heterocycle is unsubstituted, i.e. it does not carry any substituent R 8b .
- it is substituted with R 8b .
- said 6-membered saturated heterocycle contains 1 or 2, in particular 1 , heteroatom(s) O.
- the respective 6-membered heterocycle is unsubstituted, i.e. it does not carry any substituent R 8b .
- it is substituted with R 8b .
- R 8 is phenyl-Ci-C6-alkyl, such as phenyl- CH2, wherein the phenyl moiety in each case is unsubstituted or substituted with one, two or three identical or different groups R 8b which independently of one another are selected from CN, halogen, Ci-C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, Ci-C2-halogenalkoxy and S(0) n -Ci-C6- alkyl, in particular from CN, F, CI, Br, CH 3 , OCH 3 , CF 3 , CHF 2 , OCHF 2 , OCF 3 and S(0) 2 CH 3 .
- R 8 is aryl, in particular phenyl, wherein the aryl or phenyl moiety in each case is unsubstituted or substituted with identical or different groups R 8b which independently of one another are selected from CN, halogen, Ci-C2-alkyl, Ci- C2-alkoxy, Ci-C2-halogenalkyl, Ci-C2-halogenalkoxy and S(0) n -Ci-C6-alkyl, in particular from CN, F, CI, Br, CH 3 , OCH 3 , CF 3 , CHF 2 , OCHF 2 , OCF 3 .
- R 8 is unsubstituted phenyl.
- R 8 is phenyl, that is substituted with one, two or three, in particular one, halogen, in particular selected from F, CI and Br, more specifically selected from F and CI.
- R 8 is a 5-membered heteroaryl such as pyr- rol-1 -yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1 -yl, pyrazol- 3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1 -yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2- yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, is
- R 8 is a 6-membered heteroaryl, such as pyri- din-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, py- rimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl.
- R 8 is Ci-C6-alkyl, especially Chb subsitited by a 5-membered saturated heteroaryl which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S as ring members.
- the heteroaryl is unsubstituted, i.e. it does not carry any substituent R 8b .
- it is substituted with R 8b .
- R 8 is Ci-C6-alkyl, especially Chb subsitited by a 5-membered saturated heteroaryl which contains one N as ring member.
- the heteroaryl is unsubstituted, i.e. it does not carry any substituent R 8b . According to still another embodiment of formula I, it is substituted with R 8b .
- R 8 is Ci-C6-alkyl, especially Chb subsitited by a 5-membered saturated heteroaryl which contains two N as ring members.
- the heteroaryl is unsubstituted, i.e. it does not carry any substituent R 8b . According to still another embodiment of formula I, it is substituted with R 8b .
- R 8 is Ci-C6-alkyl, especially Chb subsitited by a 5-membered saturated heteroaryl which contains three N as ring members.
- the heteroaryl is unsubstituted, i.e. it does not carry any substituent R 8b .
- R 8b it is substituted with R 8b .
- said 5-membered saturated heterocycle contains 1 or 2, in particular 1 , heteroatom(s) O.
- R 8 is Ci-C6-alkyl, especially Chb subsitited by a 5-membered saturated heteroaryl which contains one S as ring member.
- the heteroaryl is unsubstituted, i.e. it does not carry any substituent R 8b . According to still another embodiment of formula I, it is substituted with R 8b .
- R 8 is Ci-C6-alkyl, especially Chb subsitited by a 5-membered saturated heteroaryl which contains one S and one N as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R 8b . According to still another embodiment of formula I, it is substituted with R 8b . According to a further specific embodiment of formula I, R 8 is Ci-C6-alkyl, especially Chb subsitited by a 5-membered saturated heteroaryl which contains one S and two N as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R 8b . According to still another embodiment of formula I, it is substituted with R 8b .
- R 8 is Ci-C6-alkyl, especially Chb subsitited by a 5-membered saturated heteroaryl which contains one oxygen and one N as ring members.
- the heteroaryl is unsubstituted, i.e. it does not carry any substituent R 8b .
- it is substituted with R 8 .
- R 8 is Ci-C6-alkyl, especially Chb subsitited by a 5-membered saturated heteroaryl which contains one oxygen and two N as ring members.
- the heteroaryl is unsubstituted, i.e. it does not carry any substituent R 8b .
- R 8b is substituted with R 8b .
- R 8 is Ci-C6-alkyl, especially Chb subsitited by a 6-membered saturated heteroaryl which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S as ring members.
- the heteroaryl is unsubstituted, i.e. it does not carry any substituent R 8b .
- it is substituted with R 8b .
- R 8 is Ci-C6-alkyl, especially Chb subsitited by a 6-membered saturated heteroaryl which one N as ring member.
- the heteroaryl is unsubstituted, i.e. it does not carry any substituent R 8b .
- it is substituted with R 8b .
- R 8 is Ci-C6-alkyl, especially Chb subsitited by a 6-membered saturated heteroaryl which two N as ring members.
- the heteroaryl is unsubstituted, i.e. it does not carry any substituent R 8b .
- it is substituted with R 8b .
- R 8 is Ci-C6-alkyl, especially Chb subsitited by a 10-membered saturated heteroaryl which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S as ring members.
- the heteroaryl is unsubstituted, i.e. it does not carry any substituent R 8b .
- R 8b it is substituted with R 8b .
- said 10-membered saturated heterocycle contains 1 or 2, in particular 1 , heteroatom(s) N.
- R 8 is Ci-C6-alkyl, especially Chb subsitited by a 10-membered saturated heteroaryl which one N as ring members.
- the heteroaryl is unsubstituted, i.e. it does not carry any substituent R 8b .
- it is substituted with R 8b .
- R 8 is Chb substituted with a 5-membered heteroaryl such as pyrrol-1 -yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1 -yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1 -yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isoxazol-4-yl
- R 8 is Chb substituted with a 6-membered heteroaryl, such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-
- R 8 is selected from Ci-C6-alkyl, Ci-C6-halogen- alkyl, CN, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, aryl, heteroaryl, three-, four-, five- or six-membered carbocycle and heterocycle, phenoxy, and C1-C6- alkyl substituted with CN, three-, four-, five- or six-membered carbocycle and heterocycle, aryl and heteroaryl; wherein the carbocycle and heterocycle is unsubstituted or carries one, two, three or four substituents R 8b as defined below.
- R 8 is selected from Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-al- kynyl, C2-C6-halogenalkynyl, aryl, heteroaryl, cypropropyl and Ci-C6-alkyl substituted with aryl and heteroaryl; wherein the aryl and heteroaryl are unsubstituted or carries one, two, three or four substituents R 8b as defined below.
- Particularly preferred embodiments of R 8 according to the invention are in Table P8 below, wherein each line of lines P8-1 to P8-182 corresponds to one particular embodiment of the invention, wherein P8-1 to P8-182 are also in any combination with one another a preferred embodiment of the present invention.
- R 7 , R 8 together with the carbon atom to which they are bound form a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- or heterocycle; wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, wherein the heteroatom N may carry one substituent R N selected from Ci-C4-alkyl, Ci-C4-halogenalkyl and S02Ph, wherein Ph is un- substituted phenyl or phenyl that is substituted with one, two or three substituents selected from CN, Ci-C4-alkyl, halogen, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy; and wherein the heteroatom S may be in the form of its oxide SO or SO2, and wherein the carbocy- cle or heterocycle is unsubstituted or carries
- R 7 and R 8 form a 3-membered saturated carbocycle.
- the carbocycle is unsubstituted, i.e. it does not carry any substituent R 8b .
- R 8b is substituted with R 8b .
- R 7 and R 8 form a 4-membered saturated carbocycle.
- the carbocycle is unsubstituted, i.e. it does not carry any substituent R 8b .
- R 8b is substituted with R 8b .
- R 7 and R 8 form a 5-membered saturated carbocycle.
- the carbocycle is unsubstituted, i.e. it does not carry any substituent R 8b .
- R 8b is substituted with R 8b .
- R 7 and R 8 form a 6-membered saturated carbocycle.
- the carbocycle is unsubstituted, i.e. it does not carry any substituent R 8b .
- R 8b is substituted with R 8b .
- R 7 and R 8 form a 7-membered saturated carbocycle.
- the carbocycle is unsubstituted, i.e. it does not carry any substituent R 8b .
- R 8b is substituted with R 8b .
- R 7 and R 8 together with the carbon atom to which they are bound form a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered heterocycle that is unsubstituted or substituted.
- the heterocycle formed by R 7 and R 8 is saturated.
- this saturated heterocycle is unsubstituted.
- the saturated heterocycle carries one, two, three or four substituents R 78 .
- said heterocycle is four- or six-membered.
- said heterocycle is four- or six-membered.
- the heterocycle formed by R 7 and R 8 contains one, two or three, more specifically one or two, heteroatoms selected from NH and NR N , wherein R N is as defined and preferably defined below, more particularly selected from Ci-C2-alkyl, Ci-C2-halo- genalkyl and S02Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted with one methyl.
- R N is as defined and preferably defined below, more particularly selected from Ci-C2-alkyl, Ci-C2-halo- genalkyl and S02Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted with one methyl.
- it contains one or two heteroatoms NH, in particular one NH.
- it contains one or two heteroatoms NR N , in particular one NR N , wherein R N in each case is as defined and preferably defined above.
- the heterocycle formed by R 7 and R 8 contains one or two heteroatoms O. In one embodiment thereof, it contains one heteroatom O. In another embodiment, it contains two heteroatoms O.
- the heterocycle formed by R 7 and R 8 is unsubstituted, i.e. it does not carry any substituent R 78 . According to a further embodiment, it carries one, two, three or four R 78 .
- the heterocycle contains one O as heteroatom.
- the formed heterocycle is oxetane.
- the heterocycle is unsubstituted, i.e. it does not carry any substituent R 78 .
- it carries one, two, three or four R 78 .
- the heterocycle is unsubstituted, i.e. it does not carry any substituent R 78 .
- it carries one, two, three or four R 78 .
- the heterocycle is unsubstituted, i.e. it does not carry any substituent R 78 .
- it carries one, two, three or four R 78 .
- said 6-membered saturated heterocycle contains 1 or 2 heteroatoms selected from NH and NR N .
- R 7 together with R 8 and with the carbon atom to which they are bound form a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle, in particular three-, four-, five- or six-membered carbocycle, more specifically five- or six-membered carbocycle, that is unsubstituted or carries one, two, three or four substituents R 78 as defined below.
- R 7 and R 8 form a cyclopropyl, that is unsubstituted or carries one, two, three or four substituents R 78 as defined below.
- R 7 and R 8 form a cyclobutyl, that is unsubstituted or carries one, two, three or four substituents R 78 as defined below.
- R 7 and R 8 form a cyclopentyl, that is unsubstituted or carries one, two, three or four substituents R 78 as defined below.
- R 7 and R 8 form a cyclohexyl, that is unsubstituted or carries one, two, three or four substituents R 78 as defined below.
- R 7 and R 8 form a cycloheptyl, that is unsubstituted or carries one, two, three or four substituents R 78 as defined below.
- R 78 are the possible substituents for the carbo- or heterocycle formed by R 7 and R 8 and are in- dependently selected from halogen, OH, CN, NO2, SH, NH 2 , d-Ce-alkyl, d-Ce-halogenalkyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, Ci-C6-alkylthio, Ci-C6-halogenalkylthio, Ci-C4-alkoxy-Ci-C4- alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or carry one, two, three, four or five substituents R 78a selected from the group consisting of halogen, OH, C1-C4- alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy; and wherein in each case one or two CH2 groups of the carbo- or heterocycle may
- R 78 is in each case independently selected from halogen, OH, CN, SH, Ci-C6-alkyl, Ci-C6-halogenalkyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy and Ci-C6-al- kylthio. In one further preferred embodiment, R 78 is in each case independently selected from halogen, Ci-C6-alkyl and Ci-C6-halogenalkyl. In one further particular embodiment, R 78 is in each case independently selected from Ci-C6-alkyl, such as methyl and ethyl.
- R N is the substituent of the heteroatom NR N that is contained in the heterocycle formed by R 7 and R 8 in some of the inventive compounds.
- R N is selected from Ci-C4-alkyl, Ci-C4-halogenalk and S02Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted with one, two or three substituents selected from Ci-C4-alkyl.
- R N is in each case independently selected from Ci-C2-alkyl, Ci-C2-halogenalkyl and S02Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted with one methyl substituents.
- R N is in each case independently selected from Ci-C2-alkyl, more particularly methyl. In one particular embodiment, R N is in each case independently selected from S02Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted with one methyl.
- R 7 , R 8 together with the carbon atom to which they are bound form a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- or heterocycle; wherein the carbocycle or heterocycle is unsubstituted or carries one, two, three or four substituents R 78 independently selected from hal- ogen, OH , CN, N0 2 , SH, NH 2 , Ci-C 6 -alkyl, Ci-C 6 -halogenalkyl, Ci-C 6 -alkoxy, Ci-C 6 -halogen- alkoxy, Ci-C6-alkylthio, Ci-C6-halogenalkylthio, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or carry one, two, three, four or five substituent
- R 7 , R 8 together with the carbon atom to which they are bound form a saturated or partially unsaturated four-, five-, six-membered carbo- or heterocycle; wherein the carbocycle or heterocycle is unsubstituted or carries one, two, three or four substituents R 78 independently selected from halogen, Ci-C6-alkyl, Ci-C6-halogenalkyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy.
- R x1 independently selected from Ci-C4-alkyl.
- R x is in each case independently selected from Ci-C4-alkyl and phenyl that is substituted with one, two or three R x1 independently selected from Ci-C2-alkyl, more specifically R x is in each case independently selected from Ci-C4-alkyl and phenyl that is substituted with one CH3.
- S0 2 -R is the tosyl group ("Ts").
- R 7a is in each case independently selected from halogen, OH, CN, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, heteroaryl, phenyl and halogenphenyl, wherein the halogenphenyl is substituted with halogen selected from the group consisting of F, CI and Br.
- R 7a is in each case independently selected from halogen, heteroaryl, phenyl and halogenphenyl, wherein the halogenphenyl is substituted with halogen selected from the group consisting of F, CI and Br, in particular selected from F and CI.
- R 7a is in each case independently selected from halogen, CN, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C 4 -halogenalkoxy, Ci-C6-alkylthio, phenyl, and heteroaryl; wherein the heteroaryl and phenyl is substituted with halogen selected from the group consisting of F, CI and Br or by Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl, Ci-C 4 -alkoxy and C1-C4- halogenalkoxy.
- R 7a is in each case independently selected from halogen heteroaryl and phenyl wherein the heteroaryl and phenyl is substituted with halogen selected from the group consisting of F, CI and Br, in particular selected from F and CI.
- R 7b is in each case independently selected from halogen, OH, CN, SH, Ci-C6-alkyl, Ci-C6-halogenalkyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy and Ci-C6-al- kylthio. In one further preferred embodiment, R 7b is in each case independently selected from halogen, Ci-C6-alkoxy, Ci-C6-halogenalkoxy and Ci-C6-halogenalkyl. In one further particular embodiment, R 7b is in each case independently selected from Ci-C6-alkyl, such as methyl and ethyl. In one further particular embodiment, R 7b is in each case independently selected from halogen, such as F, CI and Br.
- N(C( 0)Ci-C 4 -alkyl) 2 , NH-S0 2 -R x , d-Ce-alkylthio, Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl, Ci-C 4 - alkoxy, Ci-C 4 -halogenalkoxy and S(0) n -Ci-C6-alkyl; wherein n is 0, 1 and 2;
- R 8a is in each case independently selected from C1-C6- alkylthio, Ci-C 6 -halogenalkylthio, S(0) n -Ci-C 6 -alkyl, S(0) n -aryl, such as SCH 3 , S0 2 CH 3 , S0 2 Ph.
- R 8a is in each case independently selected from NH(Ci-C 4 -alkyl), N(Ci-C 4 -alkyl) 2 , NH-S0 2 -R x , such as NH(CH 3 ), N(CH 3 ) 2 or NHS0 2 CH 3 ,
- R 8a is in each case independently selected from C 3 -C6- cycloalkyl, C 3 -C6-halogencycloalkyl, such as cyclopropyl or fully or partially halogenated cyclo- propyl.
- R 8a is in each case independently selected from C1-C6- alkoxy, Ci-C 6 -halogenalkoxy, such as OCF 3 , OCHF 2 , OCH 2 F, OCCI 3 , OCHCI 2 or OCH 2 CI, in particular OCF 3 , OCHF 2 , OCCI 3 or OCHCI 2 .
- R 8a is in each case independently selected from aryl, wherein the aryl is substituted with halogen selected from the group consisting of F, CI, Br, CH 3 , CH F 2 , OCH 3 , OCH Fs, CN or S0 2 CH 3 .
- R 8 is unsubstituted 5- or 6-membered heteroaryl.
- R 8 is 5- or 6-membered heteroaryl substituted with halogen selected from the group consisting of F, CI, Br, CH 3 , CHF 2 , OCH 3 , OCHF 3 , CN or SO2CH3.
- R 8a is in each case independently selected from halo- gen, OH, CN, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and heterocycle, wherein the heretocy- clocycle is a satureated and contains one N as a ring member.
- R 8a is in each case independently selected from halogen, OH, CN, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, phenyl, aryl, and heteroaryl, wherein the aryl and heteroaryl are substituted from the group consisting of F, CI, Br, CH3, CHF2, OCH3, OCHF3, CN or SO2CH3.
- R 8a is in each case independently selected from halogen, phenyl, halogenphenyl and heteroaryl, wherein the
- halogenphenyl is substituted with halogen selected from the group consisting of F, CI and Br, in particular selected from F and CI.
- R 8a is in each case independently selected from halogen, CN, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C6-alkoxy, Ci-C4-halogenalkoxy, Ci- C6-alkylthio, Ci-C6-halogenalkylthio, phenyl, wherein the phenyl is substituted with halogen se- lected from the group consisting of F, CI and Br or by Ci-C4-alkyl, Ci-C4-halogenalkyl, C1-C4- alkoxy and Ci-C4-halogenalkoxy.
- R 8a is in each case independently selected from halogen and phenyl wherein the phenyl is substituted with halogen selected from the group consisting of F, CI and Br, in particular selected from F and CI.
- R 8b is in each case independently selected from halogen, OH, CN, SH , Ci-C6-alkyl, Ci-C6-halogenalkyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, C1-C6- alkylthio and S(0) n -Ci-C6-alkyl.
- R 8b is in each case independently selected from halogen, Ci-C6-alkoxy, Ci-C6-halogenalkyl, Ci-C6-halogen- alkoxy and S(0) n -Ci-C6-alkyl.
- R 8b is in each case independently selected from Ci-C6-alkyl, such as methyl and ethyl. According to one further particular embodiment, R 8b is in each case independently selected from halogen, such as F, CI and Br. According to one further particular embodiment, R 8b is in each case independently selected from Ci-C6-alkoxy, such as OCH3. According to one further particular embodiment, R 8b is in each case independently selected from Ci-C4-halogenalkoxy, such as OCHF2 and OCF3. According to one further particular embodiment, R 8b is in each case independently selected from S(0) n -Ci-C 6 -alkyl. such as SO2CH3.
- R 9 is in each case independently selected from H OH, CN, NO2, SH, NH 2 , NH(Ci-C 4 -alkyl), N(Ci-C 4 -alkyl) 2 , NH-S0 2 -R x , Ci-C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, Ci- C6-alkoxy, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; and wherein
- R x is Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl, unsubstituted aryl or aryl that is substituted with one, two, three, four or five substituents R x9 independently selected from Ci-C 4 -alkyl, halogen, OH, CN, Ci-C 4 -halogenalkyl, Ci-C 4 -alkoxy and Ci-C 4 -halogenalkoxy;
- R 9 wherein the acyclic moieties of R 9 are unsubstituted or substituted with identical or different groups R 9a which independently of one another are selected from:
- R 9a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalky, Ci-C 4 -halogen- alkoxy, Ci-C6-alkylthio, aryl and phenoxy, wherein the aryl and phenoxy group is unsubstituted or unsubstituted or substituted with R 9 a selected from the group consisting of halogen, OH, Ci- C 4 -alkyl, Ci-C 4 -halogenalkyl, Ci-C 4 -alkoxy and Ci-C 4 -halogenalkoxy;
- R 9 wherein the carbocyclic, heteroaryl and aryl moieties of R 9 are unsubstituted or substituted with identical or different groups R 9b which independently of one another are selected from:
- R 9 halogen, OH, CN, Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C 4 -halogenalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 - halogencycloalkyl, Ci-C 4 -halogenalkoxy and Ci-C6-alkylthio.
- R 9 is H or Ci-C6-alkyl, in particular H or CH3.
- R 9 is OH.
- R 9 is CN
- R 9 is SH.
- R 9 is NH2, NH(Ci-C 4 -alkyl), N(Ci-C 4 -alkyl)2 or NH-S02-R X , wherein R x is Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl, unsubstituted aryl or aryl that is substituted with one, two, three, four or five substituents R x9 independently selected from Ci-C 4 -al- kyl, halogen, OH, CN, Ci-C 4 -halogenalkyl, Ci-C 4 -alkoxy, or Ci-C 4 -halogenalkoxy.
- Ci-C 4 -alkyl such as NHCH3 and N(CH3)2.
- R x is Ci-C 4 -alkyl, and phenyl that is substituted with one CH3, more specifically S02-R x is CH3 and tosyl group ("Ts").
- R 9 is Ci-C6-alkyl, in particular Ci-C 4 -alkyl, such as CH 3 or CH 2 CH 3 .
- R 9 is Ci-C6-halogenalkyl, in particular C1-C4- halogenalkyl, such as CF 3 , CHF 2 , CH 2 F, CCI 3 , CHC , CH 2 CI, CF3CH2, CCI3CH2 or CF 2 CHF 2 .
- R 9 is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C 2 -C 4 -alkynyl or C 2 -C 4 -halogenalkynyl, such as C ⁇ CH, C ⁇ CCI, C ⁇ CF. CH 2 C ⁇ CH, CH 2 C ⁇ CCI, or CH 2 C ⁇ CF.
- R 9 is Ci-C6-alkoxy, in particular C1-C4- alkoxy, more specifically Ci-C2-alkoxy such as OCH3 or OCH2CH3.
- R 9 is Ci-C6-halogenalkoxy, in particular Ci- C 4 -halogenalkoxy, more specifically Ci-C2-halogenalkoxy such as OCF3, OCHF2, OCH2F, OCCI3, OCHC or OCH2CI, in particular OCF 3 , OCHF 2 , OCCI 3 or OCHCI 2 .
- R 9 is C3-C6-cycloalkyl, in particular cyclopro- pyl.
- R 9 is C3-C6-cycloalkyl, for example cyclopro- pyl, substituted with one, two, three or up to the maximum possible number of identical or different groups R 9 b as defined and preferably herein.
- R 9 is C3-C6-halogencycloalkyl.
- R 9 is fully or partially halogenated cyclopropyl.
- R 9 is unsubstituted aryl or aryl that is substituted with one, two, three or four R 9b , as defined herein.
- R 9 is unsubstituted phenyl or phenyl that is substituted with one, two, three or four R 9b , as defined herein.
- R 9 is unsubstituted 5- or 6-membered heteroaryl. According to still a further embodiment, R 9 is 5- or 6-membered heteroaryl that is substituted with one, two or three R 9b , as defined herein.
- R 9 is in each case independently selected from H, OH, CN, SH, NH 2 , NH(Ci-C 4 -alkyl), N(Ci-C 4 -alkyl) 2 , NH-S0 2 -R x , Ci-C 6 -alkyl, C 2 -C 6 - alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy and C3-C6-cycloalkyl; wherein the acyclic moieties of R 9 are not further substituted or carry one, two, three, four or five identical or different groups R 9a as defined below and wherein the carbocyclic, heteroaryl and aryl moieties of R 9 are not further substituted or carry one, two, three, four or five identical or different groups R 9b as defined below.
- R 9 is independently selected from H OH, Ci- C6-alkyl, Ci-C6-halogenalkyl, Ci-C6-alkoxy and Ci-C6-halogenalkoxy, in particular independently selected from H, CN, OH, Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl, Ci-C 4 -alkoxy and Ci-C 4 -halogen- alkoxy.
- R 9a are the possible substituents for the acyclic moieties of R 9 .
- R 9a according to the invention is independently selected from halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, aryl and phe- noxy, wherein the aryl and phenoxy group is unsubstituted or unsubstituted or substituted with R 9 a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, C1-C4- alkoxy and Ci-C4-halogenalkoxy, in particular selected from halogen, Ci-C2-alkyl, Ci-C2-halo- genalkyl, Ci-C2-alkoxy and Ci-C2-halogenalkoxy, more specifically selected from
- R 9a is independently selected from halogen, OH, CN, Ci-C2-alkoxy, C3- C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C2-halogenalkoxy. Specifically, R 9a is
- R 9a is independently selected from halogen, such as F, CI, Br and I, more specifically F, CI and Br.
- R 9a is independently selected from OH, C3- C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C2-halogenalkoxy. Specifically, R 9a is
- R 9a is independently selected from aryl and phenoxy, wherein the aryl and phenoxy group is unsubstituted or substituted with R 9a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci- C4-halogenalkoxy, in particular selected from halogen, Ci-C2-alkyl, Ci-C2-halogenalkyl, C1-C2- alkoxy and Ci-C2-halogenalkoxy, more specifically selected from halogen, such as F, CI and Br.
- R 9a is independently selected from aryl and phenoxy, wherein the aryl and phenoxy group is unsubstituted or substituted with R 9a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci- C4-halogenalkoxy, in particular
- R 9b are the possible substituents for the carbocyclic, heteroaryl and aryl moieties of R 9 .
- R 9b according to the invention is independently selected from halogen, OH, CN, Ci-C4-alkyl, Ci- C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C4-halogen- alkoxy.
- R 9b is independently selected from halogen, CN, C1-C2- alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and C1-C2- halogenalkoxy.
- R 9 b is independently selected from F, CI, Br, OH, CN, CH3, OCH3, CHF2, OCHF2, cyclopropyl, 1 -F-cyclopropyl, 1 -CI-cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1 -C - cyclopropyl, OCF 3 , and OCHF 2 .
- R 9b is independently selected from halogen, Ci- C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and C1-C2- halogenalkoxy.
- R 9 b is independently selected from halogen, CN, OH, CH3, CHF2, OCHF2, OCF3, OCH3, cyclopropyl, 1 -F-cyclopropyl, 1 -CI-cyclopropyl, 1 ,1 -F 2 -cyclopropyl, 1 ,1 -C - cyclopropyl and halogenmethoxy, more specifically independently selected from F, CI, OH, CH3, OCH3, CHF 2 , OCH3, cyclopropyl, 1 -F-cyclopropyl, 1 -CI-cyclopropyl, 1 ,1 -F 2 -cyclopropyl, 1 ,1 -C - cyclopropyl, OCHF2 and OCF3.
- R x in the substituent NH-S02-R X is in each case independently selected from Ci-C4-alkyl, C1-C4- halogenalkyl, unsubstituted aryl and aryl that is substituted with one, two, three, four or five substituents R x9 independently selected from Ci-C4-alkyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy.
- R x is in each case independently selected from Ci-C4-alkyl, halogen, OH, CN and phenyl that is substituted with one, two or three R x9 independently selected from Ci-C2-alkyl, more specifically R x is in each case independently selected from Ci-C4-alkyl and phenyl that is substituted with one CH3, more specifically S02-R : is the tosyl group ("Ts").
- R 9 Particularly preferred embodiments of R 9 according to the invention are in Table P9 below, wherein each line of lines P9-1 to P9-12 corresponds to one particular embodiment of the invention. Thereby, for every R 9 that is present in the inventive compounds, these specific
- Ts stands for the tosylgroup S02-(p-CH3)phenyl.
- the intention relates further to novel compouds of the formula I with the R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , A, B, R 7 , R 8 and R 9 as defined above, with the proviso that
- R 3 is OR Y , R Y is not C 2 -C 6 -alkyl; or
- R 56 is not NH2 und NH-SO2-R x .
- novel compounds of the formula I having R 1 , R 2 , R 4 , R 5 , R 6 , A, B, R 7 , R 8 and R 9 as defined above and
- R 3 is in each case independently selected from halogen, OH, CN, NO2, SH, NH2, NH(Ci-C 4 - alkyl), N(Ci-C 4 -alkyl) 2 , NH(C 2 -C 4 -alkenyl), N(C 2 -C 4 -alkenyl) 2 , NH(C 2 -C 4 -alkynyl), N(C 2 -C 4 - alkynyl) 2 , NH(C 3 -C 6 -cycloalkyl), N(C 3 -C 6 -cycloalkyl) 2 , N(Ci-C 4 -alkyl)(C 2 -C 4 -alkenyl), N(Ci- C 4 -alkyl)(C 2 -C 4 -alkynyl), N(Ci-C 4 -alkyl)(C 3 -C 6 -cycloalkyl), N(C2-C 4 -al
- R Y is Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6- halogenalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, phenyl and phenyl-Ci- C6-alkyl; wherein the phenyl groups are unsubstituted or or carry one, two, three, four or five substituents selected from the group consisting of CN, halogen, OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
- R 3 wherein the acyclic moieties of R 3 are unsubstituted or substituted with groups R 3a which independently of one another are selected from:
- R 3a halogen, OH, CN , Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4- halogenalkoxy, Ci-C6-alkylthio, aryl and phenoxy; wherein the aryl and phenoxy group is unsubstituted or substituted with substituent R 31a selected from the group consisting of halogen, OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
- R 3 wherein the carbocyclic, heteroaryl and aryl moieties of R 3 are unsubstituted or substituted with groups R 3b which independently of one another are selected from:
- R 3b halogen, OH, CN , Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C 4 -halogenalkyl, C 3 -C 6 -cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio.
- novel compounds of the formula I having R 1 , R 2 , R 4 , R 5 , R 6 , A, B, R 7 , R 8 and R 9 as defined above and
- R 3 is in each case independently selected from halogen, OH , CN, NO2, SH, NH2, NH(Ci-C4- alkyl), N(Ci-C 4 -alkyl) 2 , N H(C 2 -C 4 -alkenyl), N(C 2 -C 4 -alkenyl) 2 , N H(C 2 -C 4 -alkynyl), N(C 2 -C 4 - alkynyl) 2 , N H(C 3 -C 6 -cycloalkyl), N(C 3 -C 6 -cycloalkyl) 2 , N(Ci-C 4 -alkyl)(C2-C 4 -alkenyl), N(Ci- C 4 -alkyl)(C2-C 4 -alkynyl), N(Ci-C 4 -alkyl)(C 3 -C 6 -cycloalkyl), N(C2-C 4 -alkenyl)
- R 3 wherein the acyclic moieties of R 3 are unsubstituted or substituted with groups R 3a which independently of one another are selected from:
- R 3a halogen, OH, CN , Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4- halogenalkoxy, Ci-C6-alkylthio, aryl and phenoxy; wherein the aryl and phenoxy group is unsubstituted or substituted with substituent R 31a selected from the group consisting of halogen, OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
- R 3 wherein the carbocyclic, heteroaryl and aryl moieties of R 3 are unsubstituted or substituted with groups R 3b which independently of one another are selected from: R 3b halogen, OH , CN , Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C 4 -halogenalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 - halogencycloalkyl, Ci-C 4 -halogenalkoxy and Ci-C6-alkylthio.
- R 3b halogen, OH , CN , Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C 4 -halogenalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 - halogencycloalkyl, Ci-C 4 -halogenalkoxy and Ci-C6-alkylthio.
- novel compounds of the formula I having R 1 , R2, R 3 , R 5 , R 6 , A, B, R 7 , R 8 and R 9 as defined above and
- R 4 is in each case independently selected from halogen, OH , CN , NO2, SH , N H 2 , N H(Ci-C 4 - alkyl), N(Ci-C 4 -alkyl) 2 , N H(C 2 -C 4 -alkenyl), N (C 2 -C 4 -alkenyl) 2 , N H(C 2 -C 4 -alkynyl), N (C 2 -C 4 - alkynyl) 2 , N H(C 3 -C 6 -cycloalkyl), N (C 3 -C 6 -cycloalkyl) 2 , N(Ci-C 4 -alkyl)(C 2 -C 4 -alkenyl), N (Ci- C 4 -alkyl)(C 2 -C 4 -alkynyl), N (Ci-C 4 -alkyl)(C 3 -C 6 -cycloalkyl), N (C 2
- R Y is Ci-C6-alkyl, Ci-C6-halogenalkyl, C 2 -C6-alkenyl, C 2 -C6-halogenalkenyl, C 2 -C6- alkynyl, C 2 -C6-halogenalkynyl, C 3 -C6-cycloalkyl, C 3 -C6-halogencycloalkyl, phenyl and phenyl-Ci-C6-alkyl; wherein the phenyl groups are unsubstituted or or carry one, two, three, four or five substituents selected from the group consisting of CN , halogen, OH , Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl, Ci-C 4 -alkoxy and Ci-C 4 - halogenalkoxy;
- R 4 wherein the acyclic moieties of R 4 are unsubstituted or substituted with groups R 4a which independently of one another are selected from:
- R 4a halogen, OH , CN , d-Ce-alkoxy, C 3 -C6-cycloalkyl, C 3 -C6-halogencycloalkyl, Ci-C 4 - halogenalkoxy, Ci-C6-alkylthio, phenoxy; wherein the phenoxy group is unsubstituted or substituted with substituent R 41 a selected from the group consisting of halogen, OH , Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl, Ci-C 4 -alkoxy and Ci-C 4 -halogen- alkoxy;
- R 4 wherein the carbocyclic, heteroaryl and aryl moieties of R 4 are unsubstituted or substituted with groups R 4b which independently of one another are selected from:
- R 4b halogen, OH , CN , Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C 4 -halogenalkyl, C 3 -C 6 -cycloalkyl, C 3 -C6-halogencycloalkyl, Ci-C 4 -halogenalkoxy and Ci-C6-alkylthio.
- novel compounds of the formula I having R 1 , R2, R 3 , R 5 , R 6 , A, B, R 7 , R 8 and R 9 as defined above and
- R 4 is in each case independently selected from halogen, OH , CN , N0 2 , SH , N H 2 , N H(Ci-C 4 - alkyl), N(Ci-C 4 -alkyl) 2 , N H(C 2 -C 4 -alkenyl), N (C 2 -C 4 -alkenyl) 2 , N H(C 2 -C 4 -alkynyl), N (C 2 -C 4 - alkynyl) 2 , N H(C 3 -C 6 -cycloalkyl), N (C 3 -C 6 -cycloalkyl) 2 , N(Ci-C 4 -alkyl)(C 2 -C 4 -alkenyl), N (Ci- C 4 -alkyl)(C 2 -C 4 -alkynyl), N (Ci-C 4 -alkyl)(C 3 -C 6 -cycloalkyl), N
- R Y is Ci-C6-alkyl, Ci-C6-halogenalkyl, C 2 -C6-alkenyl, C 2 -C6-halogenalkenyl, C 2 -C6- alkynyl, C 2 -C6-halogenalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, phenyl and phenyl-Ci-C6-alkyl; wherein the phenyl groups are unsubstituted or or carry one, two, three, four or five substituents selected from the group consisting of CN, halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and C1-C4- halogenalkoxy;
- R 4 wherein the acyclic moieties of R 4 are unsubstituted or substituted with groups R 4a which independently of one another are selected from:
- R 4a halogen, OH, CN, d-Ce-alkoxy, Cs-Ce-cycloalkyl, Cs-Ce-halogencycloalkyl, C1-C4- halogenalkoxy, Ci-C6-alkylthio, aryl and phenoxy; wherein the aryl and phenoxy group is unsubstituted or substituted with substituent R 41a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
- R 4 wherein the carbocyclic, heteroaryl and aryl moieties of R 4 are unsubstituted or substituted with groups R 4b which independently of one another are selected from:
- R 4b halogen, OH, CN, Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C 4 -halogenalkyl, C 3 -C 6 -cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio.
- novel compounds of the formula I having R 1 , R 2 , R 3 , R 4 , A, B, R 7 , R 8 and R 9 as defined above and
- R 5 , R 6 together with the carbon atoms to which they are bound form a phenyl or five- or six membered heteroaryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S, and wherein the phenyl or heteroaryl is substituted with (R 56 ) 0 , wherein
- o 0, 1 , 2 or 3;
- R' and R" are independently selected from H , Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl or aryl; wherein the heterocycle or heteroaryl contains one, two or three heteroatoms selected from N, O and S, and wherein R' and R" are independently unsubstituted or substituted with R'" which is independently selected from halogen, OH , CN, N0 2 , SH, NH 2 , NH(Ci-C 4 -alkyl), N(Ci-C 4 -alkyl) 2 , NH-SO2- R x , Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogen
- R 56 wherein the acyclic moieties of R 56 are not further substituted or carry 1 , 2, 3 or up to the maximum possible number of identical or different groups R 56a which independently of one another are selected from:
- R 56a halogen, OH, CN , Ci-C 6 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 3 -C 6 - halogencycloalkyl, C3-C6-halogencycloalkenyl, Ci-C 4 -halogenalkoxy, Ci-C6-al- kylthio, five- or six-membered heteroaryl, phenyl and phenoxy; wherein the heteroaryl, phenyl and phenoxy group is unsubstituted or unsubstituted or substituted with R 561a selected from the group consisting of halogen, OH, Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl, Ci-C 4 -alkoxy and Ci-C 4 -halogenalkoxy;
- R 56 wherein the carbocyclic, phenyl, heterocyclic and heteroaryl moieties of R 56 are unsubstituted or substituted with identical or different groups R 56b which independently of one another are selected from:
- R 56b halogen, OH, CN , Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C 4 -halogenalkyl, C 3 -C 6 -cycloalkyl, C3-C6-halogencycloalkyl, Ci-C 4 -halogenalkoxy, and Ci-C6-alkylthio.
- the novel compounds of the formula I having R 1 , R 2 , R 3 , R 4 , A, B, R 7 , R 8 and R 9 as defined above and
- R 5 , R 6 together with the carbon atoms to which they are bound form a phenyl or five- or six membered heteroaryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S, and wherein the phenyl or heteroaryl is substituted with (R 56 ) 0 , wherein
- o 0, 1 , 2 or 3;
- R' and R" are independently selected from H , Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl or aryl; wherein the heterocycle or heteroaryl contains one, two or three heteroatoms selected from N , O and S, and wherein R' and R" are independently unsubstituted or substituted with R'" which is independently selected from halogen, OH , CN , N0 2 , SH , N H 2 , N H(Ci-C 4 -alkyl), N(Ci-C 4 -alkyl) 2 , N H-SO2- R x , d-Ce-alkyl, d-Ce-halogenalkyl, C 2 -C 6 -alkenyl
- R 56 wherein the acyclic moieties of R 56 are not further substituted or carry 1 , 2, 3 or up to the maximum possible number of identical or different groups R 56a which independently of one another are selected from:
- R 56a halogen, OH , CN , Ci-C 6 -alkoxy, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 3 -C 6 - halogencycloalkyl, C3-C6-halogencycloalkenyl, Ci-C 4 -halogenalkoxy, Ci-C6-al- kylthio, five- or six-membered heteroaryl, phenyl and phenoxy; wherein the het- eroaryl, phenyl and phenoxy group is unsubstituted or unsubstituted or substituted with R 561 a selected from the group consisting of halogen, OH , Ci-C 4 -alkyl, Ci-C 4 -halogenalkyl, Ci-C 4 -alkoxy and Ci-C 4 -halogenalkoxy;
- R 56 wherein the carbocyclic, phenyl, heterocyclic and heteroaryl moieties of R 56 are unsubstituted or substituted with identical or different groups R 56b which independently of one another are selected from:
- R 56b halogen, OH , CN , Ci-C 4 -alkyl, Ci-C 4 -alkoxy, Ci-C 4 -halogenalkyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 - halogencycloalkyl, Ci-C 4 -halogenalkoxy, and Ci-C6-alkylthio.
- Particular embodiments of the compounds I are the following compounds: l-A, l-B, l-C, l-D, l-E, l-F, l-G.
- substituents B, R 4 , R 3 are independently as defined in claim 1 or preferably defined below:
- Preferred embodiments of the present invention are the following compounds I.A-1 , I.A-2, I.A-3, I.A-4J.A-5, I.A-6, I.A-7, l-A-8; I.B-1 , I.B-2, I.B-3, I.B-4, I.B-5, I.B-6, I.B-7, I.B-8; I.C-1 , I.C-2, I.C-3, I.C-4 I.C-5, I.C-6, I.C-7, I.C-8; I.D-1 , I.D-2, I.D-3, I.D-4, I.D-5, I.D-6, I.D-7, I.D-8; I.E-1 , I.E-2, I.E- 3, I.E-4, I.E-5, I.E-6, I.E-7, I.E-8; I.F-1 , I.F-2, I.F-3, I.F-4, I.F-5, I.F-6, I.F-7, I.
- Table 1-1 Compounds of the formula I.A-1, I.B-1, I.C-1, I.D-1, I.E-1, I.F-1, I.G-1 in which R 3 is CH3 and the meaning for the combination of R 4 , R 7 and R 8 for each individual compound corresponds in each case to one line of Table A (compounds I.A-1.1-1.A-1 to I.
- A-1.1-1.A-450 com- pounds I.B-1.1-1.A-1 to I.B-1.1-1.A-450, compounds I.C-1.1-1.A-1 to I.C-1.1-1.A-450, compounds I.D-1.1-1.A-1 to I.D-1.1-1.A-450, compounds I.E-1.1-1.A-1 to I.E-1.1-1.A-450, compounds I.F-1.1-1.A-1 to I.F-1.1-1.A-450, compounds I.G-1.1-1.A-1 to I.G-1.1-1.A-450).
- Table 1-2 Compounds of the formula I.A-1, I.B-1, I.C-1, I.D-1, I.E-1, I.F-1, I.G-1 in which R 3 is CH2F and the meaning for the combination of R 4 , R 7 and R 8 for each individual compound corre- sponds in each case to one line of Table A (compounds I.A-1.1-2.A-1 to I.A-1.1-2.A-450, compounds I.B-1.1-2.A-1 to I.B-1.1-2.
- A-450 compounds I.C-1.1-2.A-1 to I.C-1.1-2.A-450, compounds I.D-1.1-2.A-1 to I.D-1.1-2.A 50, compounds I.E-1.1-2.A-1 to I.E-1.1-2. A-450, compounds I.F-1.1-2.A-1 to I.F-1.1-2.A-450, compounds I.G-1.1-2.A-1 to I.G-1.1-2.A-450).
- Table 1-3 Compounds of the formula I.A-1, I.B-1, I.C-1, I.D-1, I.E-1, I.F-1, I.G-1 in which R 3 is CHF2 and the meaning for the combination of R 4 , R 7 and R 8 for each individual compound corresponds in each case to one line of Table A (compounds I.A-1.1-3.A-1 to I.A-1.1-3.A-450, compounds I.B-1.1-3.A-1 to I.B-1.1-3.A-450, compounds I.C-1.1-3.A-1 to I.C-1.1-3.A-450, compounds I.D-1.1-3.A-1 to I.D-1.1-3.A-450, compounds I.E-1.1-3.A-1 to I.E-1.1-3.A-450, com- pounds I.F-1.1-3.A-1 to I.F-1.1-3.A-450, compounds I.G-1.1 -3.A-1 to I.G-1.1-3.A-450).
- Table 1-4 Compounds of the formula I.A-1, I.B-1, I.C-1, I.D-1, I.E-1, I.F-1, I.G-1 in which R 3 is CF3 and the meaning for the combination of R 4 , R 7 and R 8 for each individual compound corresponds in each case to one line of Table A (compounds I.A-1.1-4.A-1 to I.A-1.1-4.A-450, compounds I.B-1.1-4.A-1 to I.B-1.1-4.A-450, compounds I.C-1.1-4.A-1 to I.C-1.1-4.A-450, com- pounds I.D-1.1-4.A-1 to I.D-1.1-4.A-450, compounds I.E-1.1-4.A-1 to I.E-1.1-4. A-450, compounds I.F-1.1-4.A-1 to I.F-1.1-4.A-450, compounds I.G-1.1-4.A-1 to I.G-1.1-4.A-450).
- Table 1-5 Compounds of the formula I.A-1, I.B-1, I.C-1, I.D-1, I.E-1, I.F-1, I.G-1 in which R 3 is CI and the meaning for the combination of R 4 , R 7 and R 8 for each individual compound corresponds in each case to one line of Table A (compounds I.A-1.1-5.A-1 to I.A-1.1-5.A-450, com- pounds I.B-1.1-5.A-1 to I.B-1.1-5.A-450, compounds I.C-1.1-5.A-1 to I.C-1.1-5.A-450, compounds I.D-1.1-5.A-1 to I.D-1.1-5.A-450, compounds I.E-1.1-5.A-1 to I.E-1.1-5.A-450, compounds I.F-1.1-5.A-1 to I.F-1.1-5.A-450, compounds I.G-1.1-5.A-1 to I.G-1.1-5.A-450).
- Table 1-6 Compounds of the formula I.A-1, I.B-1, I.C-1, I.D-1, I.E-1, I.F-1, I.G-1 in which R 3 is OCH3 and the meaning for the combination of R 4 , R 7 and R 8 for each individual compound corre- sponds in each case to one line of Table A (compounds I.A-1.1-6.A-1 to I.A-1.1-6.A-450, compounds I.B-1.1-6.A-1 to I.B-1.1-6.A-450, compounds I.C-1.1-6.A-1 to I.C-1.1-6.A-450, compounds I.D-1.1-6.A-1 to I.D-1.1-6.A-450, compounds I.E-1.1-6.A-1 to I.E-1.1-6.A-450, compounds I.F-1.1-6.A-1 to I.F-1.1-6.A-450, compounds I.G-1.1-6.A-1 to I.G-1.1-6.A-450).
- Table 2-1 Compounds of the formula I.A-2, I.B-2, I.C-2, I.D-2, I.E-2, I.F-2, I.G-2 in which R 3 is CH3 and the meaning for the combination of R 4 , R 7 and R 8 for each individual compound corresponds in each case to one line of Table A (compounds I.A-2.2-1.A-1 to I.A-2.2-1.A-450, compounds I.B-2.2-1.A-1 to I.B-2.2-1.A-450, compounds I.C-2.2-1.A-1 to I.C-2.2-1.A-450, compounds I.D-2.2-1.A-1 to I.D-2.2-1.A-450, compounds I.E-2.2-1.A-1 to I.E-2.2-1.A-450, compounds I.F-2.2-1.A-1 to I.F-2.2-1.A-450, compounds I.G-2.2-1.A-1 to I.G-2.2-1.A-450).
- Table 2-2 Compounds of the formula I.A-2, I.B-2, I.C-2, I.D-2, I.E-2, I.F-2, I.G-2 in which R 3 is CH2F and the meaning for the combination of R 4 , R 7 and R 8 for each individual compound corresponds in each case to one line of Table A (compounds I.A-2.2-2.A-1 to I.A-2.2-2.A-450, compounds I.B-2.2-2.A-1 to I.B-2.2-2. A-450, compounds I.C-2.2-2.A-1 to I.C-2.2-2.A-450, compounds I.D-2.2-2.A-1 to I.D-2.2-2.A-450, compounds I.E-2.2-2.A-1 to I.E-2.2-2. A-450, com- pounds I.F-2.2-2.A-1 to I.F-2.2-2.A-450, compounds I.G-2.2-2.A-1 to I.G-2.2-2.A-450).
- Table 2-3 Compounds of the formula I.A-2, I.B-2, I.C-2, I.D-2, I.E-2, I.F-2, I.G-2 in which R 3 is CHF2 and the meaning for the combination of R 4 , R 7 and R 8 for each individual compound corresponds in each case to one line of Table A (compounds I.A-2.2-3.A-1 to I.A-2.2-3.A-450, compounds I.B-2.2-3.A-1 to I.B-2.2-3.A-450, compounds I.C-2.2-3.A-1 to I.C-2.2-3.A-450, com- pounds I.D-2.2-3.A-1 to I.D-2.2-3.A-450, compounds I.E-2.2-3.A-1 to I.E-2.2-3. A-450, compounds I.F-2.2-3.A-1 to I.F-2.2-3.A-450, compounds I.G-2.2-3.A-1 to I.G-2.2-3.A-450).
- Table 2-4 Compounds of the formula I.A-2, I.B-2, I.C-2, I.D-2, I.E-2, I.F-2, I.G-2 in which R 3 is CF3 and the meaning for the combination of R 4 , R 7 and R 8 for each individual compound corresponds in each case to one line of Table A (compounds I.A-2.2-4.A-1 to I.A-2.2-4.A-450, compounds I.B-2.2-4.A-1 to I. B-2.2-4. A-450, compounds I.C-2.2-4.A-1 to I.C-2.2-4.A-450, compounds I.D-2.2-4.A-1 to I.D-2.2-4.A-450, compounds I.E-2.2-4.A-1 to I. E-2.2-4. A-450, com- pounds I.F-2.2-4.A-1 to I.F-2.2-4.A-450, compounds I.G-2.2-4.A-1 to I.G-2.2-4.A-450).
- Table 2-5 Compounds of the formula I.A-2, I. B-2, I.C-2, I.D-2, I. E-2, I.F-2, I.G-2 in which R 3 is CI and the meaning for the combination of R 4 , R 7 and R 8 for each individual compound corresponds in each case to one line of Table A (compounds I.A-2.2-5.A-1 to I.A-2.2-5.A-450, compounds I.B-2.2-5.A-1 to I.B-2.2-5.A-450, compounds I.C-2.2-5.A-1 to I.C-2.2-5.A-450, com- pounds I.D-2.2-5.A-1 to I.D-2.2-5.A-450, compounds I.E-2.2-5.A-1 to I.E-2.2-5.A-450, compounds I.F-2.2-5.A-1 to I.F-2.2-5.A-450, compounds I.G-2.2-5.A-1 to I.G-2.2-5.A-450).
- Table 2-6 Compounds of the formula I.A-2, I. B-2, I.C-2, I.D-2, I. E-2, I.F-2, I.G-2 in which R 3 is OCH3 and the meaning for the combination of R 4 , R 7 and R 8 for each individual compound corresponds in each case to one line of Table A (compounds I.A-2.2-6.A-1 to I.A-2.2-6.A-450, com- pounds I.B-2.2-6.A-1 to I.B-2.2-6.A-450, compounds I.C-2.2-6.A-1 to I.C-2.2-6.A-450, compounds I.D-2.2-6.A-1 to I.D-2.2-6.A-450, compounds I.E-2.2-6.A-1 to I.E-2.2-6.A-450, compounds I.F-2.2-6.A-1 to I.F-2.2-6.A-450, compounds I.G-2.2-6.A-1 to I.G-2.2-6.A-450).
- Table 3-1 Compounds of the formula I.A-3, I.B-3, I.C-3, I.D-3, I.E-3, I.F-3, I.G-3 in which R 3 is CH3 and the meaning for the combination of R 4 , R 7 and R 8 for each individual compound corre- sponds in each case to one line of Table A (compounds I.A-3.3-1 .A-1 to I.A-3.3-1.A-450, compounds I.B-3.3-1.A-1 to I.B-3.3-1 .A-450, compounds I.C-3.3-1 .A-1 to I.C-3.3-1 .A-450, compounds I.D-3.3-1 .A-1 to I.D-3.3-1 .A-450, compounds I.E-3.3-1.A-1 to I.E-3.3-1 .A-450, compounds I.F-3.3-1 .A-1 to I.F-3.3-1.A-450, compounds I.G-3.3-1.A-1 to I.G-3.3-1.A-450).
- Table 3-2 Compounds of the formula I.A-3, I.B-3, I.C-3, I.D-3, I.E-3, I.F-3, I.G-3 in which R 3 is CH2F and the meaning for the combination of R 4 , R 7 and R 8 for each individual compound corresponds in each case to one line of Table A (compounds I.A-3.3-2.A-1 to I.A-3.3-2.A-450, compounds I.B-3.3-2.A-1 to I.B-3.3-2.A-450, compounds I.C-3.3-2.A-1 to I.C-3.3-2.A-450, compounds I.D-3.3-2.A-1 to I.D-3.3-2.
- A-450 compounds I.E-3.3-2.A-1 to I.E-3.3-2.A-450, compounds I.F-3.3-2.A-1 to I.F-3.3-2. A-450, compounds I.G-3.3-2.A-1 to I.G-3.3-2.A-450).
- Table 3-3 Compounds of the formula I.A-3, I.B-3, I.C-3, I.D-3, I.E-3, I.F-3, I.G-3 in which R 3 is CHF2 and the meaning for the combination of R 4 , R 7 and R 8 for each individual compound corresponds in each case to one line of Table A (compounds I.A-3.3-3.A-1 to I.A-3.3-3.A-450, compounds I.B-3.3-3.A-1 to I.B-3.3-3.A-450, compounds I.C-3.3-3.A-1 to I.C-3.3-3.A-450, compounds I.D-3.3-3.A-1 to I.D-3.3-3.
- Table 3-4 Compounds of the formula I.A-3, I.B-3, I.C-3, I.D-3, I.E-3, I.F-3, I.G-3 in which R 3 is CF3 and the meaning for the combination of R 4 , R 7 and R 8 for each individual compound corresponds in each case to one line of Table A (compounds I.A-3.3-4.A-1 to I.A-3.3-4.A-450, compounds I.B-3.3-4.A-1 to I.B-3.3-4.A-450, compounds I.C-3.3-4.A-1 to I.C-3.3-4.A-450, com- pounds I.D-3.3-4.A-1 to I.D-3.3-4.
- A-450 compounds I.E-3.3-4.A-1 to I.E-3.3-4.A-450, compounds I.F-3.3-4.A-1 to I.F-3.3-4. A-450, compounds I.G-3.3-4.A-1 to I.G-3.3-4.A-450).
- Table 3-5 Compounds of the formula I.A-3, I.B-3, I.C-3, I.D-3, I.E-3, I.F-3, I.G-3 in which R 3 is CI and the meaning for the combination of R 4 , R 7 and R 8 for each individual compound corresponds in each case to one line of Table A (compounds I.A-3.3-5.A-1 to I.A-3.3-5.A-450, compounds I.B-3.3-5.A-1 to I.B-3.3-5.A-450, compounds I.C-3.3-5.A-1 to I.C-3.3-5.A-450, compounds I.D-3.3-5.A-1 to I.D-3.3-5.A-450, compounds I.E-3.3-5.A-1 to I.E-3.3-5.A-450, com- pounds I.F-3.3-5.A-1 to I.F-3.3-5.A-450, compounds I.G-3.3-5.A-1 to I.G-3.3-5.A-450).
- Table 3-6 Compounds of the formula I.A-3, I.B-3, I.C-3, I.D-3, I.E-3, I.F-3, I.G-3 in which R 3 is OCH3 and the meaning for the combination of R 4 , R 7 and R 8 for each individual compound corresponds in each case to one line of Table A (compounds I.A-3.3-6.A-1 to I.A-3.3-6.A-450, compounds I.B-3.3-6.A-1 to I.B-3.3-6.A-450, compounds I.C-3.3-6.A-1 to I.C-3.3-6.A-450, com- pounds I.D-3.3-6.A-1 to I.D-3.3-6.
- Table 4-1 Compounds of the formula I.A-4, I.B-4, I.C-4, I.D-4, I.E-4, I.F-4, I.G-4 in which R 3 is CH3 and the meaning for the combination of R 4 , R 7 and R 8 for each individual compound corre- sponds in each case to one line of Table A (compounds I.A-4.4-1 .A-1 to I.A-4.4-1.A-450, compounds I.B-4.4-1.A-1 to I.B-4.4-1 .A-450, compounds I.C-4.4-1 .A-1 to I.C-4.4-1 .A-450, compounds I.D-4.4-1 .A-1 to I.D-4.4-1 .A-450, compounds I.E-4.4-1.A-1 to I.E-4.4-1 .A-450, compounds I.F-4.4-1 .A-1 to I.F-4.4-1.A-450, compounds I.G-4.4-1.A-1 to I.G-4.4-1.A-450).
- Table 4-2 Compounds of the formula I.A-4, I.B-4, I.C-4, I.D-4, I.E-4, I.F-4, I.G-4 in which R 3 is CH2F and the meaning for the combination of R 4 , R 7 and R 8 for each individual compound corresponds in each case to one line of Table A (compounds I.A-4.4-2.A-1 to I.A-4.4-2.A-450, compounds I.B-4.4-2.A-1 to I.B-4.4-2. A-450, compounds I.C-4.4-2.A-1 to I.C-4.4-2.A-450, compounds I.D-4.4-2.A-1 to I.D-4.4-2.A-450, compounds I.E-4.4-2.A-1 to I.E-4.4-2. A-450, compounds I.F-4.4-2.A-1 to I.F-4.4-2.A-450, compounds I.G-4.4-2.A-1 to I.G-4.4-2.A-450).
- Table 4-3 Compounds of the formula I.A-4, I.B-4, I.C-4, I.D-4, I.E-4, I.F-4, I.G-4 in which R 3 is CHF2 and the meaning for the combination of R 4 , R 7 and R 8 for each individual compound corresponds in each case to one line of Table A (compounds I.A-4.4-3.A-1 to I.A-4.4-3.A-450, compounds I.B-4.4-3.A-1 to I.B-4.4-3.A-450, compounds I.C-4.4-3.A-1 to I.C-4.4-3.A-450, compounds I.D-4.4-3.A-1 to I.D-4.4-3.A-450, compounds I.E-4.4-3.A-1 to I.E-4.4-3. A-450, com- pounds I.F-4.4-3.A-1 to I.F-4.4-3.A-450, compounds I.G-4.4-3.A-1 to I.G-4.4-3.A-450).
- Table 4-4 Compounds of the formula I.A-4, I.B-4, I.C-4, I.D-4, I.E-4, I.F-4, I.G-4 in which R 3 is CF3 and the meaning for the combination of R 4 , R 7 and R 8 for each individual compound corresponds in each case to one line of Table A (compounds I.A-4.4-4.A-1 to I.A-4.4-4.A-450, compounds I.B-4.4-4.A-1 to I.B-4.4-4.
- A-450 compounds I.C-4.4-4.A-1 to I.C-4.4-4.A-450, com- pounds I.D-4.4-4.A-1 to I.D-4.4-4.A-450, compounds I.E-4.4-4.A-1 to I.E-4.4-4. A-450, compounds I.F-4.4-4.A-1 to I.F-4.4-4.A-450, compounds I.G-4.4-4.A-1 to I.G-4.4-4.A-450).
- Table 4-5 Compounds of the formula I.A-4, I.B-4, I.C-4, I.D-4, I.E-4, I.F-4, I.G-4 in which R 3 is CI and the meaning for the combination of R 4 , R 7 and R 8 for each individual compound corresponds in each case to one line of Table A (compounds I.A-4.4-5.A-1 to I.A-4.4-5.A-450, com- pounds I.B-4.4-5.A-1 to I.B-4.4-5.A-450, compounds I.C-4.4-5.A-1 to I.C-4.4-5.A-450, compounds I.D-4.4-5.A-1 to I.D-4.4-5.A-450, compounds I.E-4.4-5.A-1 to I.E-4.4-5.A-450, compounds I.F-4.4-5.A-1 to I.F-4.4-5.A-450, compounds I.G-4.4-5.A-1 to I.G-4.4-5.A-450).
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Abstract
The present invention relates to use of the compounds of formula (I) wherein the variables are defined as given in the description and claims. The invention further relates to he novel compounds and composition for compounds of formula (I).
Description
Pyridine compounds
Description
The present invention relates to the use of pyridine compounds and the N-oxides and the salts thereof for combating phytopathogenic fungi, and to the novel compound and methods for combating phytopathogenic fungi and to seeds coated with at least one such compound. The invention also relates to to compositions comprising at least one compound I .
In many cases, in particular at low application rates, the fungicidal activity of the known fungicidal compounds is unsatisfactory. Based on this, it was an object of the present invention to provide compounds having improved activity and/or a broader activity spectrum against phytopathogenic harmful fungi.
Surprisingly, this object is achieved by the use of the inventive pyridine compounds of formula I having favorable fungicidal activity against phytopathogenic fungi.
Accordingly, the present invention relates to Use of compounds of formula I
wherein
R1 is in each case independently selected from H, halogen, OH, CN, NO2, SH, NH2, NH(Ci- C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6- alkoxy, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the het- eroaryl contains one, two or three heteroatoms selected from N, O and S; wherein
Rx is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted with substituents Rx1 independently selected from Ci-C4-alkyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the acyclic moieties of R1 are unsubstituted or substituted with groups R1a which independently of one another are selected from:
R1a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4- halogenalkoxy, Ci-C6-alkylthio, aryl and phenoxy, wherein the aryl and phenoxy group is unsubstituted or substituted with substituents R11a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the carbocyclic, heteroaryl and aryl moieties of R1 are unsubstituted or substituted with groups R1b which independently of one another are selected from:
R1 b halogen, OH, CN , Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio;
is in each case independently selected from H, halogen, OH, CN, NO2, SH, NH2, NH(Ci- C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6- alkoxy, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; wherein Rx is as defined above;
wherein the acyclic moieties of R2 are unsubstituted or substituted with groups R2a which independently of one another are selected from:
R2a halogen, OH, CN , Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci- C4-halogenalkoxy, Ci-C6-alkylthio, aryl and phenoxy, wherein the aryl and phe- noxy group is unsubstituted or substituted with substituents R22a selected from the group consisting of halogen, OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, C1-C4- alkoxy and Ci-C4-halogenalkoxy;
wherein the carbocyclic, heteroaryl and aryl moieties of R2 are unsubstituted or substituted with groups R2b which independently of one another are selected from:
R2b halogen, OH, CN , Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cyclo- alkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio;
is in each case independently selected from halogen, OH , CN, NO2, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, N H(C2-C4-alkenyl), N(C2-C4-alkenyl)2, N H(C2-C4-al- kynyl), N(C2-C4-alkynyl)2, N H(C3-C6-cycloalkyl), N(C3-C6-cycloalkyl)2, N(Ci-C4-alkyl)(C2- C4-alkenyl), N(Ci-C4-alkyl)(C2-C4-alkynyl), N(Ci-C4-alkyl)(C3-C6-cycloalkyl), N(C2-C4- alkenyl)(C2-C4-alkynyl), N(C2-C4-alkenyl)(C3-C6-cycloalkyl), N(C2-C4-alkynyl)(C3-C6-cyclo- alkyl), NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, S(0)n-Ci-C6-alkyl, S(0)n- aryl, Ci-C6-cycloalkylthio, S(0)n-C2-C6-alkenyl, S(0)n-C2-C6-alkynyl, CH(=0), C(=0)Ci- Ce-alkyl, C(=0)C2-C6-alkenyl, C(=0)C2-C6-alkynyl, C(=0)C3-C6-cycloalkyl, C(=0)N H(Ci- Ce-alkyl), CH(=S), C(=S)Ci-C6-alkyl, C(=S)C2-C6-alkenyl, C(=S)C2-C6-alkynyl, C(=S)C3- Ce-cycloalkyl, C(=S)N H(Ci-C6-alkyl), Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2- C6-alkynyl, ORY, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; wherein Rx and n is as defined above;
RY is Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6- alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, phenyl and phenyl-Ci-C6-alkyl; wherein the phenyl groups are unsubstituted or or carry one, two, three, four or five substituents selected from the group consisting of CN, halogen, OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and C1-C4- halogenalkoxy;
wherein the acyclic moieties of R3 are unsubstituted or substituted with groups R3a which independently of one another are selected from:
R3a halogen, OH, CN , Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4-
halogenalkoxy, Ci-C6-alkylthio, aryl and phenoxy; wherein the aryl and phenoxy group is unsubstituted or substituted with substituent R31a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the carbocyclic, heteroaryl and aryl moieties of R3 are unsubstituted or substituted with groups R3b which independently of one another are selected from:
R3b halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio;
R4 is in each case independently selected from halogen, OH, CN, NO2, SH, NH2,
NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH(C2-C4-alkenyl), N(C2-C4-alkenyl)2, NH(C2-C4-al- kynyl), N(C2-C4-alkynyl)2, NH(C3-C6-cycloalkyl), N(C3-C6-cycloalkyl)2, N(Ci-C4-alkyl)(C2- C4-alkenyl), N(Ci-C4-alkyl)(C2-C4-alkynyl), N(Ci-C4-alkyl)(C3-C6-cycloalkyl), N(C2-C4- alkenyl)(C2-C4-alkynyl), N(C2-C4-alkenyl)(C3-C6-cycloalkyl), N(C2-C4-alkynyl)(C3-C6-cyclo- alkyl), NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, S(0)n-Ci-C6-alkyl, S(0)n- aryl, Ci-C6-cycloalkylthio, S(0)n-C2-C6-alkenyl, S(0)n-C2-C6-alkynyl, CH(=0), C(=0)Ci- Ce-alkyl, C(=0)C2-C6-alkenyl, C(=0)C2-C6-alkynyl, C(=0)C3-C6-cycloalkyl, C(=0)NH(Ci- Ce-alkyl), CH(=S), C(=S)Ci-C6-alkyl, C(=S)C2-C6-alkenyl, C(=S)C2-C6-alkynyl, C(=S)C3- Ce-cycloalkyl, C(=S)NH(Ci-C6-alkyl), Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2- C6-alkynyl, ORY, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; wherein Rx and n is as defined above;
RY is Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6- alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, phenyl and phenyl-Ci-C6-alkyl; wherein the phenyl groups are unsubstituted or or carry one, two, three, four or five substituents selected from the group consisting of CN, halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and C1-C4- halogenalkoxy;
wherein the acyclic moieties of R4 are unsubstituted or substituted with groups R4a which independently of one another are selected from:
R4a halogen, OH, CN, d-Ce-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4- halogenalkoxy, Ci-C6-alkylthio, aryl and phenoxy; wherein the aryl and phenoxy group is unsubstituted or substituted with substituent R41a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the carbocyclic, heteroaryl and aryl moieties of R4 are unsubstituted or substituted with groups R4b which independently of one another are selected from:
R4b halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio;
R3, R4 together with the carbon atoms to which they are bound form a five- , six-, or seven- membered carbo-, heterocyclic or heteroaromatic ring; wherein the heterocyclic or het- eroaromatic ring contains 1 , 2, 3 or 4 heteroatoms selected from N, O and S; wherein N may carry one substituent RN selected from Ci-C4-alkyl, Ci-C4-halogenalkyl and S02Ph,
wherein Ph is unsubstituted or substituted with substituents selected from Ci-C4-alkyl, halogen, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy, and CN; and wherein S may be in the form of its oxide SO or SO2; and wherein in each case one or two CH2 groups of the carbo- or heterocycle may be replaced by a group independently selected from C(=0) and C(=S); and wherein the carbo-, heterocyclic or heteroaromatic ring is substituent by (R34)m, wherein m is 0, 1 , 2, 3 or 4;
R34 is in each case independently selected from halogen, OH, CN, NO2, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, Ci-C6-alkoxy, C3-C6-cycloalkyl, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl and aryl; wherein the heterocycle and heteroaryl contains 1 , 2 or 3 heteroatoms selected from N, O and S; and wherein in each case one or two CH2 groups of the carbo- or heterocycle may be replaced by a group independently selected from C(=0) and C(=S); and wherein Rx is as defined above;
wherein the acyclic moieties of R34 are unsubstituted or substituted with identical or different groups R34a which independently of one another are selected from:
R34a halogen, OH, CN, d-Ce-alkoxy, Cs-Ce-cycloalkyl, Cs-Ce-halogencycloal- kyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, aryl and phenoxy; wherein the aryl and phenoxy group is unsubstituted or substituted with R341a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogen- alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy, CN, C3-C6-cycloalkyl, C3-C6- halogencycloalkyl, Ci-C4-alkylthio;
wherein the carbocyclic, heterocyclic, heteroaryl and aryl moieties of R34 are unsubstituted or substituted with identical or different groups R34b which independently of one another are selected from:
R34b halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, Cs-Ce- cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, and Ci-C6-al- kylthio;
, R6 together with the carbon atoms to which they are bound form a phenyl or five- or six membered heteroaryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S, and wherein the phenyl or heteroaryl is substituted with (R56)0, wherein
o is 0, 1 , 2 or 3; and
R56 are independently selected from halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-al- kyl), N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, CH(=0), C(=0)Ci-C6-alkyl, C(=0)NH(Ci-C6-alkyl), CR'=NOR", Ci-C6-alkyl, Ci-C6- halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, S(0)n- Ci-C6-alkyl, three-, four-, five- or six-membered saturated or partially unsaturated
heterocycle, five- or six-membered heteroaryl and phenyl; wherein the heterocy- cle or heteroaryl contains one, two or three heteroatoms selected from N, O and S; wherein n and Rx are as defined above;
wherein R' and R" are independently selected from H , Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl or aryl; wherein the heterocycle or heteroaryl contains one, two or three heteroatoms selected from N, O and S, and wherein R' and R" are independently unsubstituted or substituted with R'" which is independently selected from halogen, OH , CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH-SO2- Rx, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6- alkynyl, C2-C6-halogenalkynyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, C3-C6-cycloal- kyl, C3-C6-halogencycloalkyl and phenyl; wherein Rx is defined above; and
wherein the acyclic moieties of R56 are not further substituted or carry 1 , 2, 3 or up to the maximum possible number of identical or different groups R56a which independently of one another are selected from:
R56a halogen, OH, CN , Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6- halogencycloalkyl, C3-C6-halogencycloalkenyl, Ci-C4-halogenalkoxy, Ci-C6-al- kylthio, five- or six-membered heteroaryl, phenyl and phenoxy; wherein the heteroaryl, phenyl and phenoxy group is unsubstituted or unsubstituted or substituted with R561a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the carbocyclic, phenyl, heterocyclic and heteroaryl moieties of R56 are unsubstituted or substituted with identical or different groups R56b which independently of one another are selected from:
R56b halogen, OH, CN , Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, and Ci-C6-alkylthio; is O or S;
is -C(R7R8)-S(0)p-, -C(R7R8)-0-, -C(R7R8)-NR9-, -C(R7R8)-C(=0)-, -C(R7R8)-C(=S)- or - C(R7)=N-; wherein
p is 0, 1 or 2; and
, R8 are independently selected from hydrogen, halogen, OH, CN, NO2, SH, Ci-C6-alkylthio, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6- alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, Ci-C6-alkoxy, C1-C6- halogenalkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, CH(=0), C(=0)Ci-C6-alkyl,
C(=0)0(Ci-C6-alkyl), C(=0)N H(Ci-C6-alkyl), C(=0)N(Ci-C6-alkyl)2, CR'=NOR", a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, a five- or six-membered heteroaryl or aryl; wherein in
each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(=0) and C(=S), and wherein the heterocycle and the heteroaryl contain independently one, two, three or four heteroatoms selected from N , O and S; and wherein Rx, R', R" and R'" are as defined above; wherein the acyclic moieties of R7 and R8 are independently not further substituted or carry 1 , 2, 3 or up to the maximum possible number of identical or different groups R7a or R8a, respectively, which independently of one another are selected from:
C4-alkyl), N (C(=0)Ci-C4-alkyl)2, N H-S02-Rx, d-C6-alkoxy, C3-C6-cycloalkyl, C3- C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, Ci-C6-halogen- alkylthio, S(0)n-Ci-C6-alkyl, S(0)n-aryl, CH(=0), C(=0)Ci-C6-alkyl,
Ce-alkyl), C(=0)N H(Ci-C6-alkyl), C(=0)N(Ci-C6-alkyl)2, CR'=NOR", a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-mem- bered carbocycle or heterocycle, aryl, phenoxy, a five-, six- or ten-membered heteroaryl; wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(=0) and C(=S); wherein the heterocycle and the heteroaryl contain independently 1 , 2, 3 or 4 heteroatoms selected from N , O and S; wherein the carbocyclic, heterocyclic, aryl and phenyl groups are independently unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH , CN , N02, SH , N H2, N H(Ci-C4-alkyl), N(Ci-C4-alkyl)2, N H(C(=0)Ci-C4-alkyl), N
alkyl)2, N H-S02-Rx, Ci-C6-alkylthio, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy, and S(0)n-Ci-C6-alkyl; and wherein Rx, R', R" and R'" are as defined above;
n is 0, 1 , 2;
wherein the carbocyclic, heterocyclic, heteroaryl and aryl moieties of R7 and R8 are independently not further substituted or carry 1 , 2, 3, 4, 5 or up to the maximum number of identical or different groups R7b or R8b, respectively, which independently of one another are selected from:
C4-alkyl), N (C(=0)Ci-C4-alkyl)2, N H-S02-Rx, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-hal- ogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci- Ce-alkylthio, Ci-C6-halogenalkylthio, S(0)n-Ci-C6-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or substituted with substituents selected from the group consisting of halogen, OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
and wherein Rx and n is as defined above; or
, R8 together with the carbon atom to which they are bound form a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or
heterocycle; wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, wherein the heteroatom N may carry one substituent selected from Ci-C4-alkyl, Ci-C4-halogenalkyl and S02Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted with one, two or three substituents selected from CN, C1-C4- alkyl, halogen, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy; and wherein the heteroatom S may be in the form of its oxide SO or SO2, and wherein the carbocycle or heterocycle is unsubstituted or carries one, two, three or four substituents R78 independently selected from halogen, OH, CN, NO2, SH, NH2, d-Ce-alkyl, d-Ce-halogen- alkyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, Ci-C6-alkylthio, Ci-C6-halogenalkylthio, C1-C4- alkoxy-Ci-C4-alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or carry one, two, three, four or five substituents R78a selected from the group consisting of CN, halogen, OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy; and wherein in each case one or two CH2 groups of the carbo- or heterocycle may be replaced by a group independently selected from C(=0) and C(=S); and
R9 is in each case independently selected from H, OH, CN, SH, NH2, NH(Ci-C4-alkyl), N(Ci- C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, C3-C6-cy- cloalkyl, saturated or partially unsaturated three-, four-, five-, six-, seven, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl and aryl;
wherein the heterocycle and heteroaryl contains 1 , 2 or 3 heteroatoms selected from N, O and S; and wherein in each case one or two CH2 groups of the carbo- or heterocycle may be replaced by a group independently selected from C(=0) and C(=S); and wherein
Rx is as defined above;
wherein the acyclic moieties of R9 are unsubstituted or carry 1 , 2, 3 or up to the maximum possible number of identical or different groups R9a which independently of one another are selected from:
R9a halogen, OH, CN , d-Ce-alkoxy, Cs-Ce-cycloalkyl, Cs-Ce-halogencycloalkyl, Ci- C4-halogenalkoxy, Ci-C6-alkylthio, aryl and phenoxy, wherein the aryl and phenyl group is unsubstituted or unsubstituted or substituted with R9a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy, CN, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-al- kylthio;
wherein the carbocyclic, heterocyclic, heteroaryl and aryl moieties of R9 are unsubstituted or substituted with identical or different groups R9b which independently of one another are selected from:
R9b halogen, OH, CN , Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, Cs-Ce-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, and Ci-C6-alkylthio; and the N-oxides and the agriculturally acceptable salts of the compounds of formula I for combating phytopathogenic fungi.
The numbering of the ring members in the compounds of the present invention is as given in formula I above:
The numbering of the ring members and substituents in the compounds of the present invention is as given in formula I above.
A skilled person will realize that compounds of formula I can be accessed via intermediates of type IV. Those intermediates can be synthesized e.g. by combining compounds of the formula II and III upon treatment with a base like DBU or K2CO3 or others at room temperature, cooling or gentle heating (see: Bioorganic & Medicinal Chemistry, 15(17), 5912-5949; 2007 or Tetrahedron Letters 51 (14). 1852-1855; 2010).
IV
X = SH, OH, NH2
Alternatively, intermediates IV can be accessed by starting from compounds of the formula VI and VII upon treatment with NaH in apolar or dipolar aprotic solvents at room temperature. Subsequent reduction e.g. with Fe in AcOH gives intermediates IV (see: Bioorganic & Medicinal Chemistr 15(17), 5912-5949; 2007).
X = SH, OH, NH2
Intermediates of type IV can be coupled with bromopyridines of type V, e.g. with K2CO3 and Cul/tmeda in toluene upon heating to gives target compounds I (see: PCT Int. Appl., 2007089034, 09 Aug 2007 or JP,2017-001998.A).
IV V
X = S, O, NH
For X = S, compounds can be treated with mCPBA in CH2CI2 at room temperature to yield the respective sulfoxides and sulfones (see: JP, 2017-001998.A).
The conversion of carbonyl derivatives into the respective thiocarbonyl analogs can be conducted upon treatment with Lawesson's reagent in THF (see: Monatshefte fuer Chemie, 1 19(12), 1439- 44;
For X = N H2, compounds of type VIII can be converted with esters of type IX in EtOH at 0 °C to yield intermediates X (see: European Journal of Medicinal Chemistry, 124, 31 1 -325; 2016).
Coupling of intermediates X with bromopyridines V, e.g. with K2CO3 and Cul/tmeda in toluene upon heating gives target compounds I (see: PCT Int. Appl., 2007089034, 09 Aug 2007 or JP
X V
The N-oxides may be prepared from the inventive compounds according to conventional oxida- tion methods, e. g. by treating compounds I with an organic peracid such as metachloroper- benzoic acid (cf. WO 03/64572 or J. Med. Chem. 38(1 1 ), 1892-903, 1995); or with inorganic oxidizing agents such as hydrogen peroxide (cf. J. Heterocyc. Chem. 18(7), 1305-8, 1981 ) or ox- one (cf. J. Am. Chem. Soc. 123(25), 5962-5973, 2001 ). The oxidation may lead to pure mono- N-oxides or to a mixture of different N-oxides, which can be separated by conventional methods such as chromatography.
In the following, the intermediate compounds are further described. A skilled person will readily understand that the preferences for the substituents, also in particular the ones given in the tables below for the respective substituents, given herein in connection with compounds I apply for the intermediates accordingly. Thereby, the substituents in each case have independently of each other or more preferably in combination the meanings as defined herein.
If the synthesis yields mixtures of isomers, a separation is generally not necessarily required since in some cases the individual isomers can be interconverted during work-up for use or during application (e. g. under the action of light, acids or bases). Such conversions may also take place after use, e. g. in the treatment of plants in the treated plant, or in the harmful fungus to be
controlled.
In the definitions of the variables given above, collective terms are used which are generally representative for the substituents in question. The term "Cn-Cm" indicates the number of carbon atoms possible in each case in the substituent or substituent moiety in question.
The term "halogen" refers to fluorine, chlorine, bromine and iodine.
The term "Ci-C6-alkyl" refers to a straight-chained or branched saturated hydrocarbon group having 1 to 6 carbon atoms, e.g. methyl, ethyl, propyl, 1 -methylethyl, butyl, 1 -methylpropyl, 2- methylpropyl, 1 ,1 -dimethylethyl, pentyl, 1 -methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dime- thylpropyl, 1 -ethylpropyl, 1 ,1 -dimethylpropyl, 1 ,2-dimethylpropyl, hexyl, 1 -methylpentyl, 2- methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 ,1 -dimethylbutyl, 1 ,2-dimethylbutyl, 1 ,3-dimethyl- butyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1 -ethylbutyl, 2-ethylbutyl, 1 ,1 ,2-tri- methylpropyl, 1 ,2,2-trimethylpropyl, 1 -ethyl-1 -methylpropyl and 1 -ethyl-2-methylpropyl. Likewise, the term "C2-C4-alkyl" refers to a straight-chained or branched alkyl group having 2 to 4 carbon atoms, such as ethyl, propyl (n-propyl), 1 -methylethyl (iso-propoyl), butyl, 1 -methylpropyl (sec- butyl), 2-methylpropyl (iso-butyl), 1 ,1 -dimethylethyl (tert. -butyl).
The term "Ci-C6-halogenalkyl" refers to an alkyl group having 1 or 6 carbon atoms as defined above, wherein some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above. Examples are "Ci-C2-halogenalkyl" groups such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlor- ofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1 -chloroethyl, 1 -bromoethyl, 1 -fluoro- ethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro- 2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl or pentafluoroethyl.
The term "Ci-C6-hydroxyalkyl" refers to an alkyl group having 1 or 6 carbon atoms as defined above, wherein some or all of the hydrogen atoms in these groups may be replaced by OH groups.
The term "Ci-C4-alkoxy-Ci-C4-alkyl" refers to alkyl having 1 to 4 carbon atoms (as defined above), whereAccording to one hydrogen atom of the alkyl radical is replaced by a Ci-C4-alkoxy group (as defined above). Likewise, the term "Ci-C6-alkoxy-Ci-C4-alkyl" refers to alkyl having 1 to 4 carbon atoms (as defined above), whereAccording to one hydrogen atom of the alkyl radi- cal is replaced by a Ci-C6-alkoxy group (as defined above).
The term "C2-C6-alkenyl" refers to a straight-chain or branched unsaturated hydrocarbon radical having 2 to 6 carbon atoms and a double bond in any position. Examples are "C2-C4-alkenyl" groups, such as ethenyl, 1 -propenyl, 2-propenyl (allyl), 1 -methylethenyl, 1 -butenyl, 2-butenyl, 3-butenyl, 1 -methyl-1 -propenyl, 2-methyl-1 -propenyl, 1 -methyl-2-propenyl, 2-methyl-2-propenyl. The term "C2-C6-alkynyl" refers to a straight-chain or branched unsaturated hydrocarbon radical having 2 to 6 carbon atoms and containing at least one triple bond. Examples are "C2-C4-al- kynyl" groups, such as ethynyl, prop-1 -ynyl, prop-2-ynyl (propargyl), but-1 -ynyl, but-2-ynyl, but- 3-ynyl, 1 -methyl-prop-2-ynyl.
The term "Ci-C6-alkoxy" refers to a straight-chain or branched alkyl group having 1 to 6 carbon atoms which is bonded via an oxygen, at any position in the alkyl group. Examples are "C1-C4-
alkoxy" groups, such as methoxy, ethoxy, n-propoxy, 1 -methylethoxy, butoxy, 1 -methyhprop- oxy, 2-methylpropoxy or 1 ,1 -dimethylethoxy.
The term "Ci-C6-halogenalkoxy" refers to a Ci-C6-alkoxy radical as defined above, wherein some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as men- tioned above. Examples are "Ci-C4-halogenalkoxy" groups, such as OCH2F, OCHF2, OCF3, OCH2CI, OCHCI2, OCCI3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chlorothoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoro- ethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2- trichloroethoxy, OC2F5, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy,
2,3-difluoro-"propoxy, 2 chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3 bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH2-C2F5, OCF2-C2F5, 1 -fluo- romethyl-2-fluoroethoxy, 1 -chloromethyl-2-chloroethoxy, 1 -bromomethyl-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy.
The term "C2-C6-alkenyloxy" refers to a straight-chain or branched alkenyl group having 2 to 6 carbon atoms which is bonded via an oxygen, at any position in the alkenyl group. Examples are "C2-C4-alkenyloxy" groups.
The term "C2-C6-alkynyloxy" refers to a straight-chain or branched alkynyl group having 2 to 6 carbon atoms which is bonded via an oxygen, at any position in the alkynyl group. Examples are "C2-C4-alkynyloxy" groups.
The term "C3-C6-cycloalkyl" refers to monocyclic saturated hydrocarbon radicals having 3 to 6 carbon ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl. Accordingly, a saturated three-, four-, five-, six-, seven-, eight-, nine or ten-membered carbocyclyl or carbo- cycle is a "C3-Cio-cycloalkyl".
The term "C3-C6-cycloalkenyl" refers to a monocyclic partially unsaturated 3-, 4- 5- or 6-mem- bered carbocycle having 3 to 6 carbon ring members and at least one double bond, such as cy- clopentenyl, cyclopentadienyl, cyclohexadienyl. Accordingly, a partially unsaturated three-, four- , five-, six-, seven-, eight-, nine or ten-membered carbocyclyl or carbocycle is a "C3-Cio-cycloal- kenyl".
The term "C3-C8-cycloalkyl-Ci-C4-alkyl" refers to alkyl having 1 to 4 carbon atoms (as defined above), whereAccording to one hydrogen atom of the alkyl radical is replaced by a cycloalkyl radical having 3 to 8 carbon atoms (as defined above).
The term "Ci-C6-alkylthio" as used herein refers to straight-chain or branched alkyl groups having 1 to 6 carbon atoms (as defined above) bonded via a sulfur atom. Accordingly, the term "Ci- C6-halogenalkylthio" as used herein refers to straight-chain or branched halogenalkyi group hav- ing 1 to 6 carbon atoms (as defined above) bonded through a sulfur atom, at any position in the halogenalkyi group.
The term "C(=0)-Ci-C6-alkyl" refers to a radical which is attached through the carbon atom of the group C(=0) as indicated by the number valence of the carbon atom. The number of valence of carbon is 4, that of nitrogen is 3. Likewise the following terms are to be construed: NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH(C3-C6-cycloalkyl), N(C3-C6-cycloalkyl)2, C(=0)-NH(Ci-C6- alkyl), C(=0)-N(Ci-C6-alkyl)2.
The term "saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine or ten- membered heterocyclyl or heterocycle, wherein the heterocyclyl or heterocycle contains 1 , 2, 3 or 4 heteroatoms selected from N, O and S" is to be understood as meaning both saturated and partially unsaturated heterocycles, wherein the ring member atoms of the heterocycle include besides carbon atoms 1 , 2, 3 or 4 heteroatoms independently selected from the group of O, N and S. For example:
a 3- or 4-membered saturated heterocycle which contains 1 or 2 heteroatoms from the group consisting of O, N and S as ring members such as oxirane, aziridine, thiirane, oxetane, azet- idine, thiethane, [1 ,2]dioxetane, [1 ,2]dithietane, [1 ,2]diazetidine; and
a 5- or 6-membered saturated or partially unsaturated heterocycle which contains 1 , 2 or 3 heteroatoms from the group consisting of O, N and S as ring members such as 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isox- azolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazoli- dinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazoli- dinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl,
1 ,2,4-oxadiazolidin-3-yl, 1 ,2,4-oxadiazolidin-5-yl, 1 ,2,4-thiadiazolidin-3-yl, 1 ,2,4-thiadiazolidin-5- yl, 1 ,2,4-triazolidin-3-yl, 1 ,3,4-oxadiazolidin-2-yl, 1 ,3,4-thiadiazolidin-2-yl, 1 ,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien- 2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin- 3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxa- zolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5- yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4- yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-dihydropyra- zol-1 -yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropy- razol-5-yl, 3,4-dihydropyrazol-1 -yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydro- pyrazol-5-yl, 4,5-dihydropyrazol-1 -yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihy- dropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihy- drooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihy- drooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 2-piperidi- nyl, 3-piperidinyl, 4-piperidinyl, 1 ,3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hex- ahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, 1 ,3,5-hexahydrotriazin-2-yl and 1 ,2,4- hexahydrotriazin-3-yl and also the corresponding -ylidene radicals; and
a 7-membered saturated or partially unsaturated heterocycle such as tetra- and hexahydroaze- pinyl, such as 2,3,4, 5-tetrahydro[1 H]azepin-1 -,-2-,-3-,-4-,-5-,-6- or-7-yl, 3,4,5,6-tetrahy- dro[2H]azepin-2-,-3-,-4-,-5-,-6- or-7-yl, 2,3,4,7-tetrahydro[1 H]azepin-1 -,-2-,-3-,-4-,-5-,-6- or-7-yl, 2,3,6,7-tetrahydro[1 H]azepin-1 -,-2-,-3-,-4-,-5-,-6- or-7-yl, hexahydroazepin-1 -,-2-,-3- or-4-yl, tetra- and hexahydrooxepinyl such as 2,3,4,5-tetrahydro[1 H]oxepin-2-,-3-,-4-,-5-,-6- or-7-yl, 2,3,4,7-tetrahydro[1 H]oxepin-2-,-3-,-4-,-5-,-6- or-7-yl, 2,3,6,7-tetrahydro[1 H]oxepin-2-, -3-,-4-,-5- ,-6- or-7-yl, hexahydroazepin-1 -,-2-, -3- or-4-yl, tetra- and hexahydro-1 ,3-diazepinyl, tetra- and hexahydro-1 ,4-diazepinyl, tetra- and hexahydro-1 ,3-oxazepinyl, tetra- and hexahydro-1 ,4-oxa- zepinyl, tetra- and hexahydro-1 ,3-dioxepinyl, tetra- and hexahydro-1 ,4-dioxepinyl and the corresponding -ylidene radicals.
The term "substituted" refers to substitued with 1 , 2, 3 or up to the maximum possible number of substituents.
The term "5-or 6-membered heteroaryl" or "5-or 6-membered heteroaromatic" refers to aromatic ring systems incuding besides carbon atoms, 1 , 2, 3 or 4 heteroatoms independently selected from the group consisting of N, O and S, for example,
a 5-membered heteroaryl such as pyrrol-1 -yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan- 2-yl, furan-3-yl, pyrazol-1 -yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1 -yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1 ,2,4-triazolyl-1 -yl, 1 ,2,4-triazol-3-yl 1 ,2,4-triazol-5-yl, 1 ,2,4-oxadiazol-3-yl, 1 ,2,4-oxadiazol-5-yl and 1 ,2,4-thiadiazol-3-yl, 1 ,2,4-thiadiazol-5-yl; or
a 6-membered heteroaryl, such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyri- dazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl.
Agriculturally acceptable salts of the inventive compounds encompass especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, have no adverse effect on the fungicidal action of said compounds. Suitable cations are thus in particular the ions of the alkali metals, preferably sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, of the transition metals, preferably manga- nese, copper, zinc and iron, and also the ammonium ion which, if desired, may carry one to four Ci-C4-alkyl substituents and/or one phenyl or benzyl substituent, preferably diisopropylammo- nium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(Ci-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sulfoxonium. Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogensulfate, sulfate, dihydrogenphosphate, hydrogenphosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting such inventive compound with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid. The inventive compounds can be present in atropisomers arising from restricted rotation about a single bond of asymmetric groups. They also form part of the subject matter of the present invention.
Depending on the substitution pattern, the compounds of formula I and their N-oxides may have one or more centers of chirality, in which case they are present as pure enantiomers or pure di- astereomers or as enantiomer or diastereomer mixtures. Both, the pure enantiomers or dia- stereomers and their mixtures are subject matter of the present invention.
In the following, particular embodiments of the inventive compounds are described. Therein, specific meanings of the respective substituents are further detained, wherein the meanings are in each case on their own but also in any combination with one another, particular embodiments of the present invention.
Furthermore, in respect of the variables, generally, the embodiments of the compounds I also
apply to the intermediates.
R1 according to the invention is in each case independently selected from hydrogen, halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl;
wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; and wherein
Rx is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted with one, two, three, four or five substituents Rx1 independently selected from Ci-C4-alkyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the acyclic moieties of R1 are unsubstituted or substituted with identical or different groups R1a which independently of one another are selected from:
R1a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalky, Ci-C4-halogen- alkoxy, Ci-C6-alkylthio, aryl and phenoxy, wherein the aryl and phenoxy group is unsubstituted or unsubstituted or substituted with R11a selected from the group consisting of halogen, OH, Ci- C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the carbocyclic, heteroaryl and aryl moieties of R1 are unsubstituted or substituted with identical or different groups R1b which independently of one another are selected from:
R1b halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6- halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio.
For every R1 that is present in the inventive compounds, the following embodiments and preferences apply independently of the meaning of any other R1 that may be present in the ring.
According to one embodiment of formula I, R1 is H, halogen or Ci-C6-alkyl, in particular H, CH3, Et, F, CI, more specifically H, CH3, F or CI most preferred H, F or CI.
According to another embodiment of formula I, R1 is hydrogen.
According to still another embodiment of formula I, R1 is halogen, in particular Br, F or CI, more specifically F or CI.
According to another embodiment of formula I, R1 is F
According to another embodiment of formula I, R1 is CI
According to another embodiment of formula I, R1 is Br.
According to still another embodiment of formula I, R1 is OH.
According to still another embodiment of formula I, R1 is CN.
According to still another embodiment of formula I, R1 is N02.
According to still another embodiment of formula I, R1 is SH.
According to still another embodiment of formula I R1 is NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2 or NH-S02-Rx, wherein Rx is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted with one, two, three, four or five substituents Rx1 independently selected from Ci-C4-al- kyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy, or Ci-C4-halogenalkoxy. In particular
Ci-C4-alkyl, such as NHCH3 and N(CH3)2. In particular Rx is Ci-C4-alkyl, and phenyl that is substituted with one CH3, more specifically S02-Rx is CH3 and tosyl group ("Ts").
According to still another embodiment of formula I, R1 is Ci-C6-halogenalkyl, in particular C1-C4- halogenalkyl, such as CF3, CHF2, CH2F, CCI3, CHCI2, CH2CI, CF3CH2, CCI3CH2 or CF2CHF2.
According to still another embodiment of formula I, R1 is C2-C6-alkenyl or C2-C6-halogenalkenyl, in particular C2-C4-alkenyl or C2-C4-halogenalkenyl, such as CH=CH2, C(CH3)=CH2, CH=CCI2, CH=CF2, CCI=CCI2, CF=CF2, CH=CH2, CH2CH=CCI2, CH2CH=CF2, CH2CCI=CCI2, CH2CF=CF2, CCI2CH=CCI2, CF2CH=CF2, CCI2CCI=CCI2, or CF2CF=CF2.
According to still another embodiment of formula I, R1 is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as C≡CH, C≡CCI, C≡CF. CH2C≡CH, CH2C≡CCI, or CH2C≡CF.
According to still another embodiment of formula I, R1 is Ci-C6-alkoxy, in particular Ci-C4-alkoxy, more specifically Ci-C2-alkoxy such as OCH3 or OCH2CH3.
According to still another embodiment of formula I, R1 is Ci-C6-halogenalkoxy, in particular Ci- C4-halogenalkoxy, more specifically Ci-C2-halogenalkoxy such as OCF3, OCHF2, OCH2F, OCCI3, OCHC or OCH2CI, in particular OCF3, OCHF2, OCCI3 or OCHCI2.
According to still another embodiment of formula I R1 is C3-C6-cycloalkyl, in particular cyclopro- pyl.
According to still another embodiment of formula I, R1 is C3-C6-cycloalkyl, for example cyclopro- pyl, substituted with one, two, three or up to the maximum possible number of identical or different groups R1b as defined and preferably herein.
According to still another embodiment of formula I, R1 is C3-C6-halogencycloalkyl. In a special embodiment R1 is fully or partially halogenated cyclopropyl.
According to still another embodiment of formula I, R1 is unsubstituted aryl or aryl that is substituted with one, two, three or four R1b, as defined herein. In particular, R1 is unsubstituted phenyl or phenyl that is substituted with one, two, three or four R1b, as defined herein.
According to still another embodiment of formula I, R1 is unsubstituted 5- or 6-membered heteroaryl. According to still a further embodiment, R1 is 5- or 6-membered heteroaryl that is substituted with one, two or three R1b, as defined herein.
According to still another embodiment of formula l,R1 is in each case independently selected from hydrogen, halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy and C3-C6-cycloalkyl; wherein the acyclic moieties of R1 are not further substituted or carry one, two, three, four or five identical or different groups R1a as defined below and wherein the carbocyclic, heteroaryl and aryl moieties of R1 are not further substituted or carry one, two, three, four or five identical or different groups R1b as defined below.
According to still another embodiment of formula I, R1 is independently selected from hydrogen, halogen, OH, Ci-C6-alkyl, Ci-C6-halogenalkyl, Ci-C6-alkoxy and Ci-C6-halogenalkoxy, in particular independently selected from H, F, CI, Br, CN, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, C1-C4- alkoxy and Ci-C4-halogenalkoxy.
R1a are the possible substituents for the acyclic moieties of R1.
R1a according to the invention is independently selected from halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, aryl and phe- noxy, wherein the aryl and phenoxy group is unsubstituted or unsubstituted or substituted with R11a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, C1-C4- alkoxy and Ci-C4-halogenalkoxy, in particular selected from halogen, Ci-C2-alkyl, Ci-C2-halo- genalkyl, Ci-C2-alkoxy and Ci-C2-halogenalkoxy, more specifically selected from halogen, such as F, CI and Br.
In to one embodiment R1a is independently selected from halogen, OH, CN, Ci-C2-alkoxy, C3- C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C2-halogenalkoxy. Specifically, R1a is
independently selected from F, CI, OH, CN, Ci-C2-alkoxy, cyclopropyl, 1 -F-cyclopropyl, 1 -CI- cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1 -Cl2-cyclopropyl and Ci-C2-halogenalkoxy.
According to one embodiment R1a is independently selected from halogen, such as F, CI, Br and I, more specifically F, CI and Br.
According to still another embodiment of formula I, R1a is independently selected from OH, C3- C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C2-halogenalkoxy. Specifically, R1a is
independently selected from OH, cyclopropyl and Ci-C2-halogenalkoxy.
According to still another embodiment of formula I, R1a is independently selected from aryl and phenoxy, wherein the aryl and phenoxy group is unsubstituted or substituted with R11a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci- C4-halogenalkoxy, in particular selected from halogen, Ci-C2-alkyl, Ci-C2-halogenalkyl, C1-C2- alkoxy and Ci-C2-halogenalkoxy, more specifically selected from halogen, such as F, CI and Br.
R1b are the possible substituents for the carbocyclic, heteroaryl and aryl moieties of R1.
R1b according to the invention is independently selected from halogen, OH, CN, Ci-C4-alkyl, Ci- C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C4-halogen- alkoxy.
According to one embodiment thereof R1b is independently selected from halogen, CN, C1-C2- alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and C1-C2- halogenalkoxy. Specifically, R1b is independently selected from F, CI, Br, OH, CN, CH3, OCH3, CHF2, OCHF2, cyclopropyl, 1 -F-cyclopropyl, 1 -CI-cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1 -C - cyclopropyl, OCF3, and OCHF2.
According to still another embodiment thereof R1b is independently selected from halogen, Ci- C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and C1-C2- halogenalkoxy. Specifically, R1b is independently selected from halogen, CN, OH, CH3, CHF2, OCHF2, OCF3, OCH3, cyclopropyl, 1 -F-cyclopropyl, 1 -CI-cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1 -C - cyclopropyl and halogenmethoxy, more specifically independently selected from F, CI, OH, CH3, OCH3, CHF2, OCH3, cyclopropyl, 1 -F-cyclopropyl, 1 -CI-cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1 -C -
cyclopropyl, OCHF2 and OCF3.
Rx in the substituent NH-S02-RX is in each case independently selected from Ci-C4-alkyl, C1-C4- halogenalkyl, unsubstituted aryl and aryl that is substituted with one, two, three, four or five substituents Rx1 independently selected from Ci-C4-alkyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy. In particular, Rx is in each case independently selected from Ci-C4-alkyl, halogen, OH, CN and phenyl that is substituted with one, two or three Rx1 independently selected from Ci-C2-alkyl, more specifically Rx is in each case independently selected from Ci-C4-alkyl and phenyl that is substituted with one CH3, more specifically S02-Rx is the tosyl group ("Ts").
Particularly preferred embodiments of R1 according to the invention are in Table P1 below, wherein each line of lines P1 -1 to P1 -16 corresponds to one particular embodiment of the invention. Thereby, for every R1 that is present in the inventive compounds, these specific
embodiments and preferences apply independently of the meaning of any other R1 that may be present in the ring:
Table P1 :
"Ts" in the table stands for the tosylgroup S02-(p-CH3)phenyl.
R2 according to the invention is in each case independently selected from hydrogen, halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl;
wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; and wherein
Rx is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted with one, two, three, four or five substituents Rx2 independently selected from Ci-C4-alkyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the acyclic moieties of R2 are unsubstituted or substituted with identical or different groups R2a which independently of one another are selected from:
R2a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalky, Ci-C4-halogen- alkoxy, Ci-C6-alkylthio, aryl and phenoxy, wherein the aryl and phenoxy group is unsubstituted
or substituted with R21a selected from the group consisting of halogen, OH, Ci-C4-alkyl, C1-C4- halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the carbocyclic, heteroaryl and aryl moieties of R2 are unsubstituted or substituted with identical or different groups R2b which independently of one another are selected from:
R2b halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6- halogencycloalky, Ci-C4-halogenalkoxy and Ci-C6-alkylthio.
For every R2 that is present in the inventive compounds, the following embodiments and preferences apply independently of the meaning of the other R2 that may be present in the ring.
According to one embodiment of formula I, R2 is H, halogen or Ci-C6-alkyl, in particular H, CH3, Et, F, CI, more specifically H, CH3, F or CI most preferred H, F or CI.
According to another of formula I, R2 is halogen, in particular Br, F or CI, more specifically F or CI.
According to another embodiment of formula I, R2 is F
According to another embodiment of formula I, R2 is CI
According to another embodiment of formula I, R2 is Br.
According to still another embodiment of formula I, R2 is hydrogen
According to still another embodiment of formula I, R2 is OH.
According to still another embodiment of formula I, R2 is CN.
According to still another embodiment of formula I, R2 is N02.
According to still another embodiment of formula I, R2 is SH.
In a further specific embodiment R2 is NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2 or NH-S02-Rx, wherein Rx is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted with one, two, three, four or five substituents Rx2 independently selected from Ci-C4-alkyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy, or Ci-C4-halogenalkoxy. In particular Ci-C4-alkyl, such as NHCH3 and N(CH3)2. In particular Rx is Ci-C4-alkyl, and phenyl that is substituted with one CH3, more specifically S02-Rx is CH3 and tosyl group ("Ts").
According to still another embodiment of formula I, R2 is Ci-C6-alkyl, in particular Ci-C4-alkyl, such as CH3 or CH2CH3.
According to still another embodiment of formula I, R2 is Ci-C6-halogenalkyl, in particular C1-C4- halogenalkyl, such as CF3, CHF2, CH2F, CCI3, CHCI2, CH2CI, CF3CH2, CCI3CH2 or CF2CHF2.
According to still a further embodiment, R2 is C2-C6-alkenyl or C2-C6-halogenalkenyl, in particular C2-C4-alkenyl or C2-C4-halogenalkenyl, such as CH=CH2, CH=CCI2, CH=CF2, CCI=CCI2, CF=CF2, CH=CH2, CH2CH=CCI2, CH2CH=CF2, CH2CCI=CCI2, CH2CF=CF2, CCI2CH=CCI2, CF2CH=CF2, CCI2CCI=CCI2, or CF2CF=CF2.
According to still a further embodiment, R2 is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as C≡CH, C≡CCI, C≡CF. CH2C≡CH, CH2C≡CCI, or CH2C≡CF.
According to still another embodiment of formula I, R2 is Ci-C6-alkoxy, in particular Ci-C4-alkoxy, more specifically Ci-C2-alkoxy such as OCH3 or OCH2CH3.
According to still another embodiment of formula I, R2 is Ci-C6-halogenalkoxy, in particular Ci- C4-halogenalkoxy, more specifically Ci-C2-halogenalkoxy such as OCF3, OCHF2, OCH2F, OCCIs, OCHC or OCH2CI, in particular OCF3, OCHF2, OCCI3 or OCHCI2.
In a further specific embodiment R2 is C3-C6-cycloalkyl, in particular cyclopropyl.
In a further specific embodiment, R2 is C3-C6-cycloalkyl, for example cyclopropyl, substituted with one, two, three or up to the maximum possible number of identical or different groups R2b as defined and preferably herein.
According to still another embodiment of formula I, R2 is C3-C6-halogencycloalkyl. In a special embodiment R2 is fully or partially halogenated cyclopropyl.
According to still another embodiment of formula I, R2 is unsubstituted aryl or aryl that is substituted with one, two, three or four R2b, as defined herein. In particular, R2 is unsubstituted phenyl or phenyl that is substituted with one, two, three or four R2b, as defined herein.
According to still another embodiment of formula I, R2 is unsubstituted 5- or 6-membered heteroaryl. According to still a further embodiment, R2 is 5- or 6-membered heteroaryl that is substituted with one, two or three R2b, as defined herein.
According to still another embodiment of formula I, R2 is in each case independently selected from hydrogen, halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy and C3-C6-cycloalkyl; wherein the acyclic moieties of R2 are not further substituted or carry one, two, three, four or five identical or different groups R2a as defined below and wherein the cycloalkyl moieties of R2 are not further substituted or carry one, two, three, four or five identical or different groups R2b as defined below.
According to still another embodiment of formula I, R2 is independently selected from hydrogen, halogen, OH, Ci-C6-alkyl, Ci-C6-halogenalkyl, Ci-C6-alkoxy and Ci-C6-halogenalkoxy, in particular independently selected from H, F, CI, Br, CN, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, C1-C4- alkoxy and Ci-C4-halogenalkoxy.
R2a are the possible substituents for the acyclic moieties of R2.
R2a according to the invention is independently selected from halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalky, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, aryl and phenoxy, wherein the aryl and phenoxy group is unsubstituted or substituted with R22a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and C1-C4- halogenalkoxy, in particular selected from halogen, Ci-C2-alkyl, Ci-C2-halogenalkyl, C1-C2- alkoxy and Ci-C2-halogenalkoxy, more specifically selected from halogen, such as F, CI and Br. According to one embodiment R2a is independently selected from halogen, OH, CN, C1-C2- alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalky and Ci-C2-halogenalkoxy. Specifically, R2a is independently selected from F, CI, OH, CN, Ci-C2-alkoxy, cyclopropyl, 1 -F-cyclopropyl, 1 -CI- cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1 -Cl2-cyclopropyl and Ci-C2-halogenalkoxy.
According to one embodiment R2a is independently selected from halogen, such as F, CI, Br and I, more specifically F, CI and Br.
According to still another embodiment of formula I, R2a is independently selected from OH, C3- C6-cycloalkyl, C3-C6-halogencycloalky and Ci-C2-halogenalkoxy. Specifically, R2a is
independently selected from OH, cyclopropyl and Ci-C2-halogenalkoxy.
According to still another embodiment of formula I, R2a is independently selected from aryl and phenoxy, wherein the aryl and phenoxy group is unsubstituted or substituted with R22a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci- C4-halogenalkoxy, in particular selected from halogen, Ci-C2-alkyl, Ci-C2-halogenalkyl, C1-C2- alkoxy and Ci-C2-halogenalkoxy, more specifically selected from halogen, such as F, CI and Br.
R2b are the possible substituents for the carbocyclic, heteroaryl and aryl moieties of R2.
R2b according to the invention is independently selected from halogen, OH, CN, Ci-C4-alkyl, Ci- C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalky and Ci-C4-halogen- alkoxy.
According to one embodiment thereof R2b is independently selected from halogen, CN, C1-C2- alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and C1-C2- halogenalkoxy. Specifically, R2b is independently selected from F, CI, Br, OH, CN, CH3, OCH3, CHF2, OCHF2, cyclopropyl, 1 -F-cyclopropyl, 1 -CI-cyclopropyl 1 ,1 -F2-cyclopropyl, 1 ,1 -C - cyclopropyl, OCF3, and OCHF2.
According to still another embodiment thereof R2b is independently selected from halogen, Ci- C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and C1-C2- halogenalkoxy. Specifically, R2b is independently selected from halogen, OH, CH3, OCH3, CN, CHF2, OCHF2, OCF3, OCH3 cyclopropyl, 1 -F-cyclopropyl, 1 -CI-cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1 -Cl2-cyclopropyl and halogenmethoxy, more specifically independently selected from F, CI, OH, CH3, OCH3, CHF2, OCH3, cyclopropyl, 1 -F-cyclopropyl, 1 -CI-cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1 -CI2-cyclopropyl, OCHF2 and OCF3.
Particularly preferred embodiments of R2 according to the invention are in Table P2 below, wherein each line of lines P2-1 to P2-16 corresponds to one particular embodiment of the invention. Thereby, for every R2 that is present in the inventive compounds, these specific
embodiments and preferences apply independently of the meaning of any other R2 that may be present in the ring:
Table P2:
"Ts" in the table stands for the tosylgroup S02-(p-CH3)phenyl.
R3 is in each case independently selected from halogen, OH , CN , NO2, SH , N H2, N H(Ci-C4- alkyl), N(Ci-C4-alkyl)2, N H(C2-C4-alkenyl), N(C2-C4-alkenyl)2, N H(C2-C4-alkynyl), N(C2-C4- alkynyl)2, N H(C3-C6-cycloalkyl), N(C3-C6-cycloalkyl)2, N(C2-C4-alkyl)(C2-C4-alkenyl), N(C2-C4- alkyl)(C2-C4-alkynyl), N(C2-C4-alkyl)(C3-C6-cycloalkyl), N(C2-C4-alkenyl)(C2-C4-alkynyl), N(C2-C4- alkenyl)(C3-C6-cycloalkyl), N(C2-C4-alkynyl)(C3-C6-cycloalkyl), N H(C(=0)Ci-C4-alkyl),
N(C(=0)Ci-C4-alkyl)2, N H-S02-Rx, S(0)n-Ci-C6-alkyl, S(0)n-aryl, Ci-C6-cycloalkylthio, S(0)n-C2- Ce-alkenyl, S(0)n-C2-C6-alkynyl, CH(=0), C(=0)Ci-C6-alkyl, C(=0)C2-C6-alkenyl, C(=0)C2-C6- alkynyl, C(=0)C3-C6-cycloalkyl, C(=0)N H(Ci-C6-alkyl), CH(=S), C(=S)Ci-C6-alkyl, C(=S)C2-C6- alkenyl, C(=S)C2-C6-alkynyl, C(=S)C3-C6-cycloalkyl, C(=S)N H(Ci-C6-alkyl), Ci-C6-alkyl, C2-C6- alkenyl, C2-C6-alkynyl, ORY, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl;
wherein the heteroaryl contains one, two or three heteroatoms selected from N , O and S;
wherein
Rx is as defined above;
RY is Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6- alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl; phenyl and phenyl-Ci-C6-alkyl; wherein the phenyl group is unsubstituted or substituted with substituents selected from the group consisting of halogen, CN , OH , C1-C6- alkyl, Ci-C6-halogenalkyl, Ci-C6-alkoxy and Ci-C6-halogenalkoxy; wherein the acyclic moieties of R3 are unsubstituted or substituted with groups R3a which independently of one another are selected from:
R3a halogen, OH , CN , Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4- halogenalkoxy, Ci-C6-alkylthio, aryl and phenoxy, wherein the aryl and phenoxy group is unsubstituted or substituted with substituents R31 a selected from the group consisting of halogen, OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the carbocycle, heteroaryl and aryl moieties of R3 are unsubstituted or
substituted with groups R3b which independently of one another are selected from:
R3b halogen, OH , CN , Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cyclo- alkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio.
According to one embodiment of formula I, R3 is selected from the group consisting of halogen, CN , Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6- halogenalkynyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, and ORY.
According to still another embodiment of formula I, R3 is halogen, in particular F, CI, Br or I, more specifically F, CI or Br, in particular F or CI.
According to still another embodiment of formula I , R3 is F.
According to still another embodiment of formula I , R3 is CI.
According to still another embodiment of formula I , R3 is Br.
According to still another embodiment of formula I , R3 is OH.
According to still another embodiment of formula I , R3 is CN.
According to still another embodiment of formula I , R3 is N02.
According to still another embodiment of formula I , R3 is SH.
According to still another embodiment of formula I , R3 is NH2.
According to still another embodiment of formula I , R3 is , NH(C
NH(C2H5).
According to still another embodiment of formula I , R3 is , N(Ci- NH(C2H5)2.
According to still another embodiment of formula I , R3 is , NH(C
NH(CH=CH2), NH(CH2CH=CH2).
According to still another embodiment of formula I, R3 is , N(C2-C4--alkenyl)2, in particular N(CH=CH2)2, N(CH2CH=CH2)2.
According to still another embodiment of formula I, R3 is , NH(C2-C4-alkynyl), in particular NH(C= CH), NH(CH2C≡CH).
According to still another embodiment of formula I, R3 is , N(C2-C4-alkynyl)2, in particular N(C= CH)2, N(CH2C≡CH)2.
According to still another embodiment of formula I, R3 is , NH(C3-C6-cycloalkyl), in particular NH(C3H7), NH(C4H9).
According to still another embodiment of formula I, R3 is , N(C3-C6-cycloalkyl)2, in particular N(C3H7)2, N(C4H9)2.
According to still another embodiment of formula I, R3 is N(Ci-C4-alkyl)(C2-C4-alkenyl), in particular N(CH3)(CH=CH2), N(CH3)(CH2CH=CH2), N(C2H5)(CH=CH2), N(C2H5)(CH2CH=CH2).
According to still another embodiment of formula I, R3 is N(Ci-C4-alkyl)(C2-C4-alkynyl), in particular N(CH3)(C≡CH), N(CH3)(CH2C≡CH), N(C2H5)(C≡CH), N(C2H5)(CH2C≡CH).
According to still another embodiment of formula I, R3 is N(Ci-C4-alkyl)(C3-C6-cycloalkyl), in particular N(CH3)(C3H7), N(CH3)(C4H9), N(C2H5)(C3H7), N(CH3)(C4H9).
According to still another embodiment of formula I, R3 is N(C2-C4-alkenyl)(C2-C4-alkynyl), in particular N(CH=CH2)(C≡CH), N(CH2CH=CH2)(CH2C≡CH), N(CH=CH2)(C≡CH),
N(CH2CH=CH2)(CH2C≡CH).
According to still another embodiment of formula I, R3 is N(C2-C4-alkenyl)(C3-C6-cycloalkyl), in
particular N(CH=CH2)(C3H7), N(CH2CH=CH2)(C4H9), N(CH=CH2)(C3H7), N(CH2CH=CH2)(C4H9).
According to still another embodiment of formula I, R3 is N(C2-C4-alkynyl)(C3-C6-cycloalkyl), in particular N(C≡CH)(C3H7), N(CH2C≡CH)(C4H9), N(C≡CH)(C3H7), N(CH2C≡CH)(C4H9).
According to still another embodiment of formula I, R3 is , NH(C(=0)(Ci-C4-alkyl), in particular NH(C(=0)(CH3), NH(C(=0)(C2H5).
According to still another embodiment of formula I, R3 is N(C(=0)(Ci-C4-alkyl)2, in particular N(C(=0)(CH3)2, N(C(=0)(C2H5)2.
According to a further specific embodiment of formula I, R3 is NH-S02-Rx such as NH-S02-CH3, NH-S02-CH2-CH3, NH-S02-CF3, NH-S02-Ts.
According to still another embodiment of formula I, R3 is S(0)n-Ci-C6-alkyl such as SCH3, S(=0) CH3, S(0)2CH3.
According to still another embodiment of formula I, R3 is S(0)n-aryl such as S-phenyl, S(=0) phenyl, S(0)2phenyl.
According to still another embodiment of formula I, R3 is S(0)n-C2-C6-alkenyl such as
SCH=CH2, S(=0)CH=CH2, S(0)2CH=CH2, SCH2CH=CH2, S(=0)CH2CH=CH2,
S(0)2CH2CH=CH2 .
According to still another embodiment of formula I, R3 is S(0)n-C2-C6-alkynyl such as SC CH, S(=0)C≡CH, S(0)2C≡CH, SCH2C≡CH, S(=0)CH2C≡CH, S(0)2CH2C≡CH.
According to a further specific embodiment of formula I, R3 is CH(=0).
According to a further specific embodiment of formula I, R3 is C(=0)Ci-C6-alkyl, C(=0)0(Ci-C6- alkyl) or C(=0)NH(Ci-C6-alkyl), wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
According to a further specific embodiment of formula I, R3 is C(=0)C2-C6-alkenyl, C(=0)0(C2- Ce-alkenyl) or C(=0)NH(C2-C6-alkenyl), wherein alkenyl is CH=CH2, CH2CH=CH2.
According to a further specific embodiment of formula I, R3 is C(=0)C2-C6-alkynyl, C(=0)0(C2- Ce-alkynyl) or C(=0)NH(C2-C6-alkynyl), wherein alkynyl is C≡CH, CH2C≡CH.
According to a further specific embodiment of formula I, R3 is C(=0)C3-C6-cycloalkyl,
C(=0)0(C3-C6-cycloalkyl) or C(=0)NH(C3-C6-cycloalkyl), wherein cycloalkyl is cyclopropyl (C3H7) or cyclobutyl (C4H9).
According to a further specific embodiment of formula I, R3 is CH(=S).
According to a further specific embodiment of formula I, R3 is C(=S)Ci-C6-alkyl, wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
According to a further specific embodiment of formula I, R3 is C(=S)C2-C6-alkenyl, wherein alkenyl is CH=CH2, CH2CH=CH2.
According to a further specific embodiment of formula I, R3 is C(=S)C2-C6-alkynyl, wherein alkynyl is C≡CH, CH2C≡CH.
According to a further specific embodiment of formula I, R3 is C(=S)C3-C6-cycloalkyl, wherein cycloalkyl is cyclopropyl (C3H7) or cyclobutyl (C4Hg).
According to a further specific embodiment of formula I, R3 is C(=S)NHCi-C6-alkyl, wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
According to still another embodiment of formula I, R3 is Ci-C6-alkyl, in particular Ci-C4-alkyl, such as CH3. or C2H5, in particular CH3 or CH2CH3.
According to still another embodiment of formula I, R3 is Ci-C6-halogenalkyl, in particular C1-C4- halogenalkyl, such as CF3, CCI3, FCH2, CICH2, F2CH, CI2CH, CF3CH2, CCI3CH2 or CF2CHF2. According to still a further embodiment of formula I, R3 is C2-C6-alkenyl, in particular C2-C4-alk- enyl, such as CH=CH2, C(CH3)=CH2, CH2CH=CH2.
According to a further specific embodiment of formula I, R3 is C2-C6-halogenalkenyl, in particular C2-C4-halogenalkenyl, more specifically C2-C3-halogenalkenyl such as CH=CHF, CH=CHCI, CH=CF2, CH=CCI2, CH2CH=CHF, CH2CH=CHCI, CH2CH=CF2, CH2CH=CCI2, CF2CH=CF2, CCI2CH=CCI2, CF2CF=CF2, CCI2CCI=CCI2.
According to still a further embodiment of formula I, R3 is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as C CH, CH2C=CH, C=CCI,
CH2C≡CCI, or CCI2C≡CCI.
According to a further specific embodiment of formula I , R3 is ORY, wherein RY is Ci-C6-alkyl, Ci- C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3- C6-cycloalkyl, C3-C6-halogencycloalkyl.
According to a further specific embodiment of formula I, R3 is ORY, wherein RY is Ci-C6-alkyl, in particular Ci-C4-alkyl, more specifically Ci-C2-alkoxy. R3 is such as OCH3 or OCH2CH3.
According to a further specific embodiment of formula I, R3 is ORY, wherein RY is Ci-C6-halogen- alkyl, in particular Ci-C4-halogenalkyl, more specifically Ci-C2-halogenalkyl. R3 is such as OCF3, OCHF2, OCH2F, OCCI3, OCHC or OCH2CI, in particular OCF3, OCHF2, OCCI3 or OCHCI2.
According to a further specific embodiment of formula I, R3 is ORY, wherein RY C2-C6-alkenyl, in particular C2-C4-alkenyl, more specifically Ci-C2-alkenyl. R3 is such as OCH=CH2,
OCH2CH=CH2.
According to a further specific embodiment of formula I, R3 is ORY, wherein RY C2-C6-halogen- alkenyl, in particular C2-C4-halogenalkenyl, more specifically Ci-C2-halogenalkenyl.
According to a further specific embodiment of formula I, R3 is ORY, wherein RY C2-C6-alkynyl, in particular C2-C6-alkynyl, in particular C2-C4-alkynyl, more specifically Ci-C2-alkynyl. R3 is such as OC≡CH,
According to a further specific embodiment of formula I, R3 is ORY, wherein RY C2-C6-halogen- alkynyl, in particular C2-C6-halogenalkynyl, in particular C2-C4-halogenalkynyl, more specifically Ci-C2-halogenalkynyl. R3 is such as OC≡CCI, OCH2C≡CCI, or OCCI2C≡CCI.
According to still another embodiment of formula I, R3 is is ORY, wherein RY C3-C6-cycloalkenyl, in particular cyclopropenyl.
According to still another embodiment of formula I, R3 is C3-C6-cycloalkyl, in particular cyclopro- pyl.
According to still another embodiment of formula I, R3 is C3-C6-halogencycloalkyl. In a special
embodiment R3b is fully or partially halogenated cyclopropyl, such as 1 -F-cyclopropyl, 1 -CI- cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1 -Cl2-cyclopropyl .
According to still another embodiment of formula I, R3 is phenyl-Ci-C6-alkyl, such as phenyl- CH2, wherein the phenyl moiety in each case is unsubstituted or substituted with one, two or three identical or different groups R3b which independently of one another are selected from halogen, Ci-C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl and Ci-C2-halogenalkoxy, in particular F, CI, Br, CH3, OCH3, CF3 and OCF3.
According to still another embodiment of formula I, R3 is aryl, in particular phenyl, wherein the aryl or phenyl moiety in each case is unsubstituted or substituted with identical or different groups R3b which independently of one another are selected from CN, halogen, Ci-C2-alkyl, Ci- C2-alkoxy, Ci-C2-halogenalkyl and Ci-C2-halogenalkoxy, in particular CN, F, CI, Br, CH3, OCH3, CHF2, OCHF2, CF3 and OCF3. According to one embodiment, R3 is unsubstituted phenyl. According to another embodiment, R3 is phenyl, that is substituted with one, two or three, in particular one, halogen, in particular selected from F, CI and Br, more specifically selected from F and CI.
According to still another embodiment of formula I, R3 is a 5-membered heteroaryl such as pyr- rol-1 -yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1 -yl, pyrazol- 3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1 -yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2- yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1 ,2,4-triazolyl-1 -yl, 1 ,2,4-triazol-3-yl 1 ,2,4-triazol-5-yl, 1 ,2,4-oxadiazol-3-yl, 1 ,2,4-oxadiazol-5-yl and 1 ,2,4-thiadiazol-3-yl, 1 ,2,4-thia- diazol-5-yl.
According to still another embodiment of formula I, R3 is a 6-membered heteroaryl such as pyri- din-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, py- rimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl.
According to still another embodiment of formula I, R3 is in each case independently selected from H, halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6- alkoxy, Ci-C6-halogenalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyl and C3-C6- halogencycloalkyl, wherein the acyclic moieties of R3 are unsubstituted or substituted with iden- tical or different groups R3a as defined and preferably defined herein, and wherein the carbocy- clic, phenyl and heteroaryl moieties of R3 are unsubstituted or substituted with identical or different groups R3b as defined and preferably defined herein.
According to still another embodiment of formula I, R3 is in each case independently selected from H, halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6- alkoxy, Ci-C6-halogenalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyl and C3-C6- halogencycloalkyl,, wherein the acyclic moieties of R3 are unsubstituted or substituted with identical or different groups R3a as defined and preferably defined herein, and wherein the cycloalkyi moieties of R3 are unsubstituted or substituted with identical or different groups R3b as defined and preferably defined herein.
R3a are the possible substituents for the acyclic moieties of R3.
According to one embodiment R3a is independently selected from halogen, OH, CN, C1-C6-
alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, aryl and phenoxy, wherein the aryl and phenyl group is unsubstituted or substituted with substitu- ents R31a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy.
According to one embodiment R3a is independently selected from halogen, Ci-C6-alkoxy, C3-C6- cycloalkyl, C3-C6-halogencycloalkyl and Ci-C4-halogenalkoxy. Specifically, R3a is independently selected from F, CI, Br, I , Ci-C2-alkoxy, cyclopropyl, 1 -F-cyclopropyl, 1 -CI-cyclopropyl, I -F2- cyclopropyl, 1 ,1 -Cl2-cyclopropyl and Ci-C2-halogenalkoxy.
According to still another embodiment of formula I , R3a is independently halogen, in particular selected from F, CI, Br and I , more specifically F, CI and Br.
R3b are the possible substituents for the carbocyclic, heteroaryl and phenyl moieties of R3. R3b according to the invention is independently selected from halogen, OH, CN , Ci-C4-alkyl, C1-C4- alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and d-Ce-alkylthio.
According to one embodiment thereof R3b is independently selected from halogen, CN, C1-C4- alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl and Ci-C4-halogenalkoxy, in particular halogen, C1-C4- alkyl and Ci-C4-alkoxy. Specifically, R3b is independently selected from F, CI, CN, CH3, OCH3 and halogenmethoxy.
Particularly preferred embodiments of R3 according to the invention are in Table P3 below, wherein each line of lines P3-1 to P3-42 corresponds to one particular embodiment of the invention, wherein P3-1 to P3-42 are also in any combination with one another a preferred embodiment of the present invention. The connection point to the carbon atom, to which R3 is bound is marked with "#" in the drawings. Table P3:
No. R3 No. R3
P3-1 CH3 P3-12 CH=CH2
P3-2 CH2F P3-13 CH2CH=CH2
P3-3 CHF2 P3-14 C≡CH
P3-4 CF3 P3-15 CH2C≡CH
P3-5 C2H5 P3-16 CH2CH2CH(CH3)2
P3-6 CH(CH3)2 P3-17 OH
P3-7 CH2CH2CH3 P3-18 OCH3
P3-8 CH2CH2CH2CH3 P3-19 OCHF2
P3-9 CH2CH(CH3)2 P3-20 OC2H5
P3-10 C(CH3)3 P3-21 CN
P3-1 1 CH2CH2CH2CH2CH3 P3-22 F
R4 is in each case independently selected from halogen, OH, CN, N02, SH, NH2, NH(Ci-C4- alkyl), N(Ci-C4-alkyl)2, NH(C2-C4-alkenyl), N(C2-C4-alkenyl)2, NH(C2-C4-alkynyl), N(C2-C4- alkynyl)2, NH(C3-C6-cycloalkyl), N(C3-C6-cycloalkyl)2, N(C2-C4-alkyl)(C2-C4-alkenyl), N(C2-C4- alkyl)(C2-C4-alkynyl), N(C2-C4-alkyl)(C3-C6-cycloalkyl), N(C2-C4-alkenyl)(C2-C4-alkynyl), N(C2-C4- alkenyl)(C3-C6-cycloalkyl), N(C2-C4-alkynyl)(C3-C6-cycloalkyl), NH(C(=0)Ci-C4-alkyl),
N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, S(0)n-Ci-C6-alkyl, S(0)n-aryl, Ci-C6-cycloalkylthio, S(0)n-C2- Ce-alkenyl, S(0)n-C2-C6-alkynyl, CH(=0), C(=0)Ci-C6-alkyl, C(=0)C2-C6-alkenyl, C(=0)C2-C6- alkynyl, C(=0)C3-C6-cyclpalkyl, C(=0)NH(Ci-C6-alkyl), CH(=S), C(=S)Ci-C6-alkyl, C(=S)C2-C6- alkenyl, C(=S)C2-C6-alkynyl, C(=S)C3-C6-cyclpalkyl, C(=S)NH(Ci-C6-alkyl), Ci-Ce-alkyI, C2-C6- alkenyl, C2-C6-alkynyl, ORY, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl;
wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S;
wherein
Rx is as defined above;
RY is as defined above;
wherein the acyclic moieties of R4 are unsubstituted or substituted with groups R4a which independently of one another are selected from:
R4a halogen, OH, CN, d-Ce-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4- halogenalkoxy, Ci-C6-alkylthio, aryl and phenoxy, wherein the aryl and phenyl group is unsubstituted or substituted with substituents R41a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the carbocyclic, heteroaryl and aryl moieties of R4 are unsubstituted or
substituted with groups R4b which independently of one another are selected from:
R4b halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio.
According to one embodiment of formula I, R4 is selected from the group consisting of halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6- halogenalkynyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy and ORY.
R4 is secected from the group consisting of halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6- alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, Ci-C6-alkoxy, Ci-C6-halo- genalkoxy and ORY.
According to still another embodiment ol formula 1, R4 is halogen, in particular F, CI, Br or 1, more specifically F, CI or Br, in particular• F or CI.
According to still another embodiment ol formula 1 , R4 is F.
According to still another embodiment ol formula 1 , R4 is CI.
According to still another embodiment ol formula 1 , R4 is Br.
According to still another embodiment ol formula 1 , R4 is OH.
According to still another embodiment o1 formula 1 , R4 is CN.
According to still another embodiment ol formula 1 , R4 is N02.
According to still another embodiment ol formula 1 , R4 is SH.
According to still another embodiment ol formula 1 , R4 is NH2.
According to still another embodiment o1 formula 1 , R4 is , NH(Ci-C4-alkyl), in particular NH(CH3), NH(C2H5).
According to still another embodiment ol formula 1 , R4 is , N(Ci-C4-alkyl)2, in particular NH(CH3)2, NH(C2H5)2.
According to still another embodiment ol formula 1 , R4 is , NH(C2-C4-alkenyl), in particular NH(CH=CH2), NH(CH2CH=CH2).
According to still another embodiment ol formula 1 , R4 is , N(C2-C4--alkenyl)2, in particular N(CH=CH2)2, N(CH2CH=CH2)2.
According to still another embodiment ol formula 1 , R4 is , NH(C2-C4-alkynyl), in particular NH(C≡ CH), NH(CH2C≡CH).
According to still another embodiment ol formula 1 , R4 is , N(C2-C4-alkynyl)2, in particular N(C= CH)2, N(CH2C≡CH)2.
According to still another embodiment ol formula 1 , R4 is , NH(C3-C6-cycloalkyl), in particular NH(C3H7), NH(C4H9).
According to still another embodiment ol formula 1 , R4 is , N(C3-C6-cycloalkyl)2, in particular N(C3H7)2, N(C4H9)2.
According to still another embodiment ol formula 1 , R4 is N(Ci-C4-alkyl)(C2-C4-alkenyl), in
particular N(CH3)(CH=CH2), N(CH3)(CH2CH=CH2), N(C2H5)(CH=CH2), N(C2H5)(CH2CH=CH2).
According to still another embodiment of formula I, R4 is N(Ci-C4-alkyl)(C2-C4-alkynyl), in particular N(CH3)(C≡CH), N(CH3)(CH2C≡CH), N(C2H5)(C≡CH), N(C2H5)(CH2C≡CH).
According to still another embodiment of formula I, R4 is N(Ci-C4-alkyl)(C3-C6-cycloalkyl), in particular N(CH3)(C3H7), N(CH3)(C4H9), N(C2H5)(C3H7), N(CH3)(C4H9).
According to still another embodiment of formula I, R4 is N(C2-C4-alkenyl)(C2-C4-alkynyl), in particular N(CH=CH2)(C≡CH), N(CH2CH=CH2)(CH2C≡CH), N(CH=CH2)(C≡CH),
N(CH2CH=CH2)(CH2C≡CH).
According to still another embodiment of formula I, R4 is N(C2-C4-alkenyl)(C3-C6-cycloalkyl), in particular N(CH=CH2)(C3H7), N(CH2CH=CH2)(C4H9), N(CH=CH2)(C3H7), N(CH2CH=CH2)(C4H9).
According to still another embodiment of formula I, R4 is N(C2-C4-alkynyl)(C3-C6-cycloalkyl), in particular N(C≡CH)(C3H7), N(CH2C≡CH)(C4H9), N(C≡CH)(C3H7), N(CH2C≡CH)(C4H9).
According to still another embodiment of formula I, R4 is , NH(C(=0)(Ci-C4-alkyl), in particular NH(C(=0)(CH3), NH(C(=0)(C2H5).
According to still another embodiment of formula I, R4 is N(C(=0)(Ci-C4-alkyl)2, in particular N(C(=0)(CH3)2, N(C(=0)(C2H5)2.
According to a further specific embodiment of formula I, R4 is NH-S02-Rx such as NH-S02-CH3, NH-S02-CH2-CH3, NH-S02-CF3, NH-S02-Ts.
According to still another embodiment of formula I, R4 is S(0)n-Ci-C6-alkyl such as SCH3, S(=0) CH3, S(0)2CH3.
According to still another embodiment of formula I, R4 is S(0)n-aryl such as S-phenyl, S(=0) phenyl, S(0)2phenyl.
According to still another embodiment of formula I, R4 is S(0)n-C2-C6-alkenyl such as
SCH=CH2, S(=0)CH=CH2, S(0)2CH=CH2, SCH2CH=CH2, S(=0)CH2CH=CH2,
S(0)2CH2CH=CH2 .
According to still another embodiment of formula I, R4 is S(0)n-C2-C6-alkynyl such as SC CH, S(=0)C≡CH, S(0)2C≡CH, SCH2C≡CH, S(=0)CH2C≡CH, S(0)2CH2C≡CH.
According to a further specific embodiment of formula I, R4 is CH(=0).
According to a further specific embodiment of formula I, R4 is C(=0)Ci-C6-alkyl, C(=0)0(Ci-C6- alkyl) or C(=0)NH(Ci-C6-alkyl), wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
According to a further specific embodiment of formula I, R4 is C(=0)C2-C6-alkenyl, C(=0)0(C2- Ce-alkenyl) or C(=0)NH(C2-C6-alkenyl), wherein alkenyl is CH=CH2, C(CH3)=CH2, CH2CH=CH2.
According to a further specific embodiment of formula I, R4 is C(=0)C2-C6-alkynyl, C(=0)0(C2- Ce-alkynyl) or C(=0)NH(C2-C6-alkynyl), wherein alkynyl is C≡CH, CH2C≡CH,
According to a further specific embodiment of formula I, R4 is C(=0)C3-C6-cycloalkyl,
C(=0)0(C3-C6-cycloalkyl) or C(=0)NH(C3-C6-cycloalkyl), wherein cycloalkyl is cyclopropyl (C3H7) or cyclobutyl (C4H9).
According to a further specific embodiment of formula I , R4 is CH(=S).
According to a further specific embodiment of formula I , R4 is C(=S)Ci-C6-alkyl, wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
According to a further specific embodiment of formula I , R4 is C(=S)C2-C6-alkenyl, wherein alkenyl is CH=CH2, CH2CH=CH2.
According to a further specific embodiment of formula I , R4 is C(=S)C2-C6-alkynyl, wherein al- kynyl is C≡CH, CH2C≡CH.
According to a further specific embodiment of formula I , R4 is C(=S)C3-C6-cycloalkyl, wherein cycloalkyl is cyclopropyl (C3H7) or cyclobutyl (C4H9).
According to a further specific embodiment of formula I, R4 is C(=S)NHCi-C6-alkyl, wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
According to still another embodiment of formula I, R4 is Ci-C6-alkyl, in particular Ci-C4-alkyl, such as CH3. or C2H5, in particular CH3 or CH2CH3.
According to still another embodiment of formula I, R4 is Ci-C6-halogenalkyl, in particular C1-C4- halogenalkyl, such as CF3, CCI3, FCH2, CICH2, F2CH, CI2CH, CF3CH2, CCI3CH2 or CF2CHF2. According to still a further embodiment of formula I, R4 is C2-C6-alkenyl, in particular C2-C4-alk- enyl, such as CH=CH2.
According to a further specific embodiment of formula I, R4 is C2-C6-halogenalkenyl, in particular C2-C4-halogenalkenyl, more specifically C2-C3-halogenalkenyl such as CH=CHF, CH=CHCI, CH=CF2, CH=CCI2, CH2CH=CHF, CH2CH=CHCI, CH2CH=CF2, CH2CH=CCI2, CF2CH=CF2, CCI2CH=CCI2, CF2CF=CF2, CCI2CCI=CCI2.
According to still a further embodiment of formula I, R4 is C2-C6-alkynyl or C2-C6-halogen- alkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as C CH, CH2 C CH, C CCI, CH2C≡CCI, or CCI2C≡CCI.
According to a further specific embodiment of formula I, R4 is ORY, wherein RY is Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl.
According to a further specific embodiment of formula I, R4 is ORY, wherein RY is Ci-C6-alkyl, in particular Ci-C4-alkyl, more specifically Ci-C2-alkoxy. R4 is such as OCH3 or OCH2CH3.
According to a further specific embodiment of formula I, R4 is ORY, wherein RY is Ci-C6-halogen- alkyl, in particular Ci-C4-halogenalkyl, more specifically Ci-C2-halogenalkyl. R4 is such as OCF3, OCHF2, OCH2F, OCCI3, OCHC or OCH2CI, in particular OCF3, OCHF2, OCCI3 or OCHCI2.
According to a further specific embodiment of formula I, R4 is ORY, wherein RY C2-C6-alkenyl, in particular C2-C4-alkenyl, more specifically Ci-C2-alkenyl. R4 is such as OCH=CH2,
OCH2CH=CH2.
According to a further specific embodiment of formula I, R4 is ORY, wherein RY C2-C6-alkynyl, in particular C2-C6-alkynyl, in particular C2-C4-alkynyl, more specifically Ci-C2-alkynyl. R4 is such as OC≡CH, OC≡CCI, OCH2C≡CCI, or OCCI2C≡CCI
According to still another embodiment of formula I R4 is ORY, wherein RY is C3-C6-cycloalkyl, in particular cyclopropyl.
According to still another embodiment of formula I, R4 is ORY, wherein RY is C3-C6-halogencyclo- alkyl. In a special embodiment R1 is fully or partially halogenated cyclopropyl.
According to still another embodiment of formula I, R4 is is ORY, wherein RY C3-C6-cycloalkenyl, in particular cyclopropenyl.
According to still another embodiment of formula I, R4 is C3-C6-cycloalkyl, in particular cyclopropyl.
According to still another embodiment of formula I, R4 is C3-C6-halogencycloalkyl. In a special embodiment R4b is fully or partially halogenated cyclopropyl, such as 1 -F-cyclopropyl, 1 -CI- cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1 -Cl2-cyclopropyl
According to still another embodiment of formula I, R4 is phenyl-Ci-C6-alkyl, such as phenyl- CH2, wherein the phenyl moiety in each case is unsubstituted or substituted with one, two or three identical or different groups R4b which independently of one another are selected from hal- ogen, Ci-C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl and Ci-C2-halogenalkoxy, in particular F, CI, Br, CH3, OCH3, CF3 and OCF3.
According to still another embodiment of formula I, R4 is aryl, in particular phenyl, wherein the aryl or phenyl moiety in each case is unsubstituted or substituted with identical or different groups R4b which independently of one another are selected from CN, halogen, Ci-C2-alkyl, Ci- C2-alkoxy, Ci-C2-halogenalkyl and Ci-C2-halogenalkoxy, in particular CN, F, CI, Br, CH3, OCH3, CHF2, OCHF2, CF3 and OCF3. According to one embodiment, R4 is unsubstituted phenyl. According to another embodiment, R4 is phenyl, that is substituted with one, two or three, in particular one, halogen, in particular selected from F, CI and Br, more specifically selected from F and CI.
According to still another embodiment of formula I, R4 is a 5-membered heteroaryl such as pyr- rol-1 -yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1 -yl, pyrazol- 3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1 -yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2- yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1 ,2,4-triazolyl-1 -yl, 1 ,2,4-triazol-3-yl 1 ,2,4-triazol-5-yl, 1 ,2,4-oxadiazol-3-yl, 1 ,2,4-oxadiazol-5-yl and 1 ,2,4-thiadiazol-3-yl, 1 ,2,4-thia- diazol-5-yl.
According to still another embodiment of formula I, R3 is a 6-membered heteroaryl such as pyri- din-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, py- rimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl.
According to still another embodiment of formula I, R4 is in each case independently selected from H, halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6- alkoxy, Ci-C6-halogenalkoxy,C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyl and C3-C6- halogencycloalkyl, wherein the acyclic moieties of R4 are unsubstituted or substituted with identical or different groups R4a as defined and preferably defined herein, and wherein the carbocy- die, phenyl and heteroaryl moieties of R4 are unsubstituted or substituted with identical or different groups R4b as defined and preferably defined herein.
According to still another embodiment of formula I, R4 is in each case independently selected from H, halogen, CN, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6- alkoxy, Ci-C6-halogenalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyl and C3-C6- halogencycloalkyl, wherein the acyclic moieties of R4 are unsubstituted or substituted with iden- tical or different groups R4a as defined and preferably defined herein, and wherein the cycloalkyi moieties of R4 are unsubstituted or substituted with identical or different groups R4b as defined and preferably defined herein.
R4a are the possible substituents for the acyclic moieties of R3.
According to one embodiment R4a is independently selected from halogen, OH, CN, C1-C6- alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, aryl and phenoxy, wherein the aryl and phenyl group is unsubstituted or substituted with substituents R41a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy.
According to one embodiment R4a is independently selected from halogen, Ci-C6-alkoxy, C3-C6- cycloalkyi, C3-C6-halogencycloalkyl and Ci-C4-halogenalkoxy. Specifically, R4a is independently selected from F, CI, Br, I, Ci-C2-alkoxy, cyclopropyl, 1 -F-cyclopropyl, 1-CI-cyclopropyl, 1 , 1 -F2- cyclopropyl, 1 ,1 -Cl2-cyclopropyl and Ci-C2-halogenalkoxy.
According to still another embodiment of formula I, R4a is independently halogen, in particular selected from F, CI, Br and I, more specifically F, CI and Br.
R4b are the possible substituents for the carbocyclic, heteroaryl and phenyl moieties of R4. R4b according to the invention is independently selected from halogen, OH, CN, Ci-C4-alkyl, C1-C4- alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and d-Ce-alkylthio.
According to one embodiment thereof R4b is independently selected from halogen, CN, C1-C4- alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl and Ci-C4-halogenalkoxy, in particular halogen, C1-C4- alkyl and Ci-C4-alkoxy. Specifically, R4b is independently selected from F, CI, CN, CH3, OCH3 and halogenmethoxy.
Particularly preferred embodiments of R4 according to the invention are in Table P4 below, wherein each line of lines P4-1 to P4-42 corresponds to one particular embodiment of the inven- tion, wherein P4-1 to P4-42 are also in any combination with one another a preferred embodiment of the present invention. The connection point to the carbon atom, to which R4 is bound is marked with "#" in the drawings.
Table P4:
No. R4
P4-1 CH3
P4-2 CH2F
P4-3 CHF2
P4-4 CF3
P4-36 S-CHs
P4-37
P4-38
P4-39
P4-40
P4-41
P4-42 •o
According to still another embodiment of formula I, R3, R4 together with the carbon atoms to which they are bound form a five- , six-, or seven- membered carbo-, heterocyclic or heteroaromatic ring; wherein the heterocyclic or heteroaromatic ring contains 1 , 2, 3 or 4 heteroatoms selected from N, O and S, wherein N may carry one substituent RN selected from Ci-C4-alkyl, Ci- C4-halogenalkyl and S02Ph, wherein Ph is unsubstituted or substituted with substituents selected from Ci-C4-alkyl, halogen, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy, and CN; and wherein S may be in the form of its oxide SO or SO2; and wherein in each case one or two CH2 groups of the carbo- or heterocycle may be replaced by a group independently selected from C(=0) and C(=S); and wherein the carbo-, heterocyclic or heteroaromatic ring is substituent by (R34)m wherein m is 0, 1 , 2, 3 or 4;
RN is the substituent of the heteroatom N that is contained in the heterocycle formed by R3 and R4 in some of the inventive compounds. RN is selected from Ci-C4-alkyl, Ci-C4-halogenalkyl and S02Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted with one, two or three substituents selected from Ci-C4-alkyl. In one preferred embodiment, RN is in each case independently selected from Ci-C2-alkyl, Ci-C2-halogenalkyl and S02Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted with one methyl substituents. In one particular embodiment, RN is in each case independently selected from Ci-C2-alkyl, more particularly methyl. In one particular embodiment, RN is in each case independently selected from S02Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted with one methyl.
According to still another embodiment of formula I, R3 and R4 together with the carbon atoms to which they are bound form a saturated or partially unsaturated five-, six-or seven -membered carbo- and heterocycle that is unsubstituted or substituted.
According to one embodiment, R3 and R4 form a 3-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R34. According to still another embodiment of formula I, it is substituted with R34.
According to one embodiment, R3 and R4 form a 4-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R34. According to still another embodiment of formula I, it is substituted with R34.
According to one embodiment, R3 and R4 form a 5-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R34. According to still another embodiment of formula I, it is substituted with R34.
According to one embodiment, R3 and R4 form a 6-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R34. According to still another embodiment of formula I, it is substituted with R34.
According to one embodiment, R3 and R4 form a 7-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R34. According to still another embodiment of formula I, it is substituted with R34.
According to one embodiment, R3 and R4 form a 3-membered saturated heterocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R34. According to still another embodiment of formula I, it is substituted with R34.
According to one embodiment, R3 and R4 form a 4-membered saturated heterocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R34. According to still another embodiment of formula I, it is substituted with R34.
According to one embodiment, R3 and R4 form a 5-membered saturated heterocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R34. According to still another embodiment of formula I, it is substituted with R34.
According to one embodiment, R3 and R4 form a 6-membered saturated heterocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R34. According to still another embodiment of formula I, it is substituted with R34.
According to one embodiment, R3 and R4 form a 7-membered saturated heterocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R34. According to still another embodiment of formula I, it is substituted with R34.
According to one embodiment, R3 and R4 form a 5-membered saturated heteroaryl. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R34. According to still another embodiment of formula I, it is substituted with R34.
According to one embodiment, R3 and R4 form a 6-membered heteroaryl. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R34. According to still another embodiment of formula I, it is substituted with R34.
R34 according to the invention is in each case independently selected from halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, Ci-C6-alkoxy, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl and aryl;
wherein the heterocycle and heteroaryl contains one, two or three heteroatoms selected from N, O and S; and wherein in each case one or two CH2 groups of the carbo- or heterocycle may be replaced by a group independently selected from C(=0) and C(=S); and wherein
Rx is as defined above;
wherein the acyclic moieties of R34 are unsubstituted or substituted with identical or different groups R34a which independently of one another are selected from:
R34a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halo- genalkoxy, Ci-C6-alkylthio, aryl and phenoxy, wherein the aryl group is unsubstituted or unsubstituted or substituted with R341a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy, CN, C3-C6-cycloalkyl, C3-C6-halogency- cloalkyl, Ci-C4-alkylthio;
wherein the carbocyclic, heterocyclic, heteroaryl and aryl of R34 are unsubstituted or substituted with identical or different groups R34b which independently of one another are selected from:
R34b halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6- halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio.
For every R34 that is present in the inventive compounds, the following embodiments and preferences apply independently of the meaning of any other R34 that may be present in the ring.
According to one embodiment of formula I, wherein m is 0, 1 , 2, 3 or 4.
According to still another embodiment of formula l,m is 0.
According to still another embodiment of formula I, m is 1.
According to still another embodiment of formula I, m is 2 or 3. According to one specific embodiment thereof, m is 2. According to still another embodiment of formula I, m is 3.
According to one embodiment of formula I, R34 is halogen, Ci-C6-alkyl, Ci-C6-halogenalkyl, Ci- Ce-alkoxy or , Ci-C6-halogenalkoxy, in particular CH3, Et, CHF2, OCH3, OCHF2, OCF3, F, CI, more specifically H, CH3, F or CI most preferred F or CI.
According to still another embodiment of formula I, R34 is halogen, in particular Br, F or CI, more specifically F or CI.
According to still another embodiment of formula I, R34 is OH.
According to still another embodiment of formula I, R34 is CN.
According to still another embodiment of formula I R34 is NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2 or NH-S02-RX, wherein Rx is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted with one, two, three, four or five substituents Rx34 independently selected from C1-C4- alkyl.
According to still another embodiment of formula I, R34 is Ci-C6-alkyl, in particular Ci-C4-alkyl, such as CH3.
According to still another embodiment of formula I, R34 is Ci-C6-halogenalkyl, in particular C1-C4- halogenalkyl, such as CF3, CHF2, CH2F, CCI3, CHCI2 or CH2CI.
According to still another embodiment of formula I, R34 is C2-C6-alkenyl or C2-C6-halogenalkenyl, in particular C2-C4-alkenyl or C2-C4-halogenalkenyl, such as CH=CH2, C(CH3)=CH2,
CH2CH=CH2, CH=CHF, CH=CHCI, CH=CF2, CH=CCI2, CF=CF2, CCI=CCI2, CH2CH=CHF, CH2CH=CHCI, CH2CH=CF2, CH2CH=CCI2, CH2CF=CF2, CH2CCI=CCI2, CF2CF=CF2 or
CCI2CCI=CCI2.
According to still another embodiment of formula I, R34 is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as C≡CH, CH2C≡CH, C≡C-CI, C≡C- CH3, CH2C≡CH, CH2C≡CCI or CH2C≡C-CH3.
According to still another embodiment of formula I, R34 is Ci-C6-alkoxy, in particular Ci-C4- alkoxy, more specifically Ci-C2-alkoxy such as OCH3 or OCH2CH3.
According to still another embodiment of formula I, R34 is Ci-C6-halogenalkoxy, in particular Ci- C4-halogenalkoxy, more specifically Ci-C2-halogenalkoxy such as OCF3, OCHF2, OCH2F, OCCIs, OCHC or OCH2CI, in particular OCF3, OCHF2, OCCI3 or OCHCI2.
According to still another embodiment of formula I R34 is C3-C6-cycloalkyl, in particular cyclopro- pyl.
According to still another embodiment of formula I, R34 is C3-C6-cycloalkyl, for example cyclopro- pyl, substituted with one, two, three or up to the maximum possible number of identical or different groups R34b as defined and preferably herein.
According to still another embodiment of formula I, R34 is C3-C6-halogencycloalkyl. In a special embodiment R34 is fully or partially halogenated cyclopropyl.
According to still another embodiment of formula I, R34 is unsubstituted aryl or aryl that is substituted with one, two, three or four R34b, as defined herein. In particular, R34 is unsubstituted phenyl or phenyl that is substituted with one, two, three or four R34b, as defined herein.
According to still another embodiment of formula I, R34 is unsubstituted 5- or 6-membered heteroaryl. According to still a further embodiment, R34 is 5- or 6-membered heteroaryl that is substituted with one, two or three R34b, as defined herein.
According to still another embodiment of formula I, R34 is in each case independently selected from halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy and C3-C6-cycloalkyl; wherein the acyclic moieties of R34 are not further substituted or carry one, two, three, four or five identical or different groups R34a as defined below and wherein the carbocyclic, heterocyclic and heteroaryl moieties of R34 are not further substituted or carry one, two, three, four or five identical or different groups R34b as defined below.
According to still another embodiment of formula I, R34 is independently selected from halogen, OH, Ci-C6-alkyl, Ci-C6-halogenalkyl, Ci-C6-alkoxy and Ci-C6-halogenalkoxy, in particular independently selected from F, CI, Br, CN, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy.
R34a are the possible substituents for the acyclic moieties of R34.
R34a according to the invention is independently selected from halogen, OH, CN, Ci-C6-alkoxy,
C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, aryl and phe- noxy, wherein the aryl and phenyl group is unsubstituted or unsubstituted or substituted with R341a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, C1-C4- alkoxy, Ci-C4-halogenalkoxy, CN, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-alkylthio. R34a according to the invention is independently selected from halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, aryl and phe- noxy, wherein the aryl and phenyl group is unsubstituted or unsubstituted or substituted with R341a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, C1-C4- alkoxy and Ci-C4-halogenalkoxy, in particular selected from halogen, Ci-C2-alkyl, Ci-C2-halo- genalkyl, Ci-C2-alkoxy, Ci-C2-halogenalkoxy, more specifically selected from halogen, such as F, CI and Br.
In to one embodiment R34a is independently selected from halogen, OH, CN, Ci-C2-alkoxy, C3- C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C2-halogenalkoxy. Specifically, R34a is
independently selected from F, CI, OH, CN, Ci-C2-alkoxy, cyclopropyl, 1 -F-cyclopropyl, 1 -CI- cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1 -Cl2-cyclopropyl and Ci-C2-halogenalkoxy.
According to one embodiment R34a is independently selected from halogen, such as F, CI, Br and I, more specifically F, CI and Br.
According to still another embodiment of formula I, R34a is independently selected from OH, C3- C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C2-halogenalkoxy. Specifically, R34a is
independently selected from OH, cyclopropyl and Ci-C2-halogenalkoxy.
R34b are the possible substituents for the carbocyclic, heterocyclic and heteroaryl moieties of R34.
R34b according to the invention is independently selected from halogen, OH, CN, Ci-C4-alkyl, Ci- C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C4-halogen- alkoxy.
According to one embodiment thereof R34b is independently selected from halogen, CN, C1-C2- alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalky and Ci-C2-hal- ogenalkoxy. Specifically, R34b is independently selected from F, CI, OH, CN, CH3, OCH3, cyclopropyl, 1 -F-cyclopropyl, 1 -CI-cyclopropyl, 1 ,1-F2-cyclopropyl, 1 ,1 -Cl2-cyclopropyl and halogenmethoxy.
According to still another embodiment thereof R34b is independently selected from Ci-C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C2-halogen- alkoxy. Specifically, R34b is independently selected from OH, CH3, OCH3, cyclopropyl, 1 -F- cyclopropyl, 1 -CI-cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1 -Cl2-cyclopropyl and halogenmethoxy, more specifically independently selected from OH, CH3, OCH3, cyclopropyl, 1 -F-cyclopropyl, 1 - Cl-cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1 -Cl2-cyclopropyl cyclopropyl and OCHF2.
Particularly preferred embodiments of combinations of R3 and R4 according to the invention are in Table P35 below, wherein each line of lines P34-1 to P34-272 corresponds to one particular embodiment of the invention, wherein P34-1 to P34-272 are also in any combination with one another a preferred embodiment of the present invention. The carbon atom, to which R3 bound is marked with * in the drawings and the carbon atom, to which R4 is bound is marked with # in
line R3 R4
P34-90 CH2F OCH2F
P34-91 CH2F OCHF2
P34-92 CH2F OCFs
P34-93 CH2F cPr
P34-94 CH2F C≡CH
P34-95 CH2F CN
P34-96 CH2F S-CHs
P34-97 CHF2 F
P34-98 CHF2 CI
P34-99 CHF2 Br
P34-100 CHF2 CHs
P34-101 CHF2 CH2CHs
P34-102 CHF2 CH2F
P34-103 CHF2 CHF2
P34-104 CHF2 CFs
P34-105 CHF2 OCHs
P34-106 CHF2 OCH2F
P34-107 CHF2 OCHF2
P34-108 CHF2 OCFs
P34-109 CHF2 cPr
P34-1 10 CHF2 C≡CH
P34-1 1 1 CHF2 CN
P34-1 12 CHF2 S-CHs
P34-1 13 CFs F
P34-1 14 CFs CI
P34-1 15 CFs Br
P34-1 16 CFs CHs
P34-1 17 CFs CH2CHs
P34-1 18 CFs CH2F
R5 and R6 together with the carbon atoms to whi Och they are bound together form a phenyl or five- or six-membered heteroaryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; and wherein the heteroaryl carries zero, one, two, three or four substituents (R56)0, wherein o is 0, 1 , 2 or 3; and
R56 are independently selected from halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl),
N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, CH(=0), C(=0)Ci-C6- alkyl, C(=0)NH(Ci-C6-alkyl), CR'=NOR", Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6- alkynyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C3-C6-cycloal-
kyl, C3-C6-cycloalkenyl, S(0)n-Ci-C6-alkyl, three-, four-, five- or six-membered saturated or partially unsaturated heterocycle, five- or six-membered heteroaryl and phenyl; wherein the hetero- cycle or heteroaryl contains one, two or three heteroatoms selected from N, O and S; wherein n, Rx, R' and R" are as defined above.
and wherein the acyclic moieties of R56 are not further substituted or carry one, two, three or up to the maximum possible number of identical or different groups R56a which independently of one another are selected from:
R56a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6-halogencyclo- alkyl, C3-C6-halogencycloalkenyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, five- or six-membered heteroaryl, phenyl and phenoxy, wherein the heteroaryl and phenyl group is unsubstituted or carries one, two, three, four or five substituents R56a' selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the carbocyclic, phenyl, heterocyclic and heteroaryl moieties of R56 are not further substituted or carry one, two, three, four, five or up to the maximum number of identical or different groups R56b which independently of one another are selected from:
R56b halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6- halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio.According to one embodiment, R5 and R6 together with the carbon atoms to which they are bound form phenyl; wherein the phenyl carries zero, one or two substituents (R56)0, as defined and preferably defined herein, wherein o is 0, 1 or 2. According to one specific embodiment, o is 0. According to a further embodiment, o is 1 or 2. Particular embodiments thereof are listed in Table P56.
According to one embodiment, R5 and R6 together with the carbon atoms to which they are bound form a five- or six-membered heteroaryl; wherein the heteroaryl contains one or two heteroatoms selected from N, O and S, and wherein the heteroaryl carries zero, one or two substit- uents (R56)0, as defined and preferably defined herein, wherein o is 0, 1 or 2. According to one specific embodiment, o is 0. According to a further embodiment, o is 1 or 2. Particular embodiments thereof are listed in Table P56.
According to a further embodiment, R5 and R6 together with the carbon atoms to which they are bound form a five- or six-membered heteroaryl; wherein the heteroaryl contains one or two heteroatoms N, and wherein the heteroaryl carries zero, one or two substituents (R56)0, as defined and preferably defined herein, wherein o is 0, 1 or 2. According to one specific embodiment, o is 0. According to a further embodiment, o is 1 or 2. Particular embodiments thereof are listed in Table P56.
According to a further embodiment, R5 and R6 together with the carbon atoms to which they are bound form a five- or six-membered heteroaryl; wherein the heteroaryl contains one or two heteroatoms selected from S and O, and wherein the heteroaryl carries zero, one or two substituents (R56)0, as defined and preferably defined herein, wherein o is 0, 1 or 2. According to one specific embodiment, o is 0. According to a further embodiment, o is 1 or 2. Particular embodiments thereof are listed in Table P56.
According to a further embodiment, R5 and R6 together with the carbon atoms to which they are bound form a five- or six-membered heteroaryl; wherein the heteroaryl contains one heteroatom
S, and wherein the heteroaryl carries zero, one or two substituents (R56)0, as defined and preferably defined herein, wherein o is 0, 1 or 2. According to one specific embodiment, o is 0. According to a further embodiment, o is 1 or 2. Particular embodiments thereof are listed in Table P56.
According to a further embodiment, R5 and R6 together with the carbon atoms to which they are bound form a five- or six-membered heteroaryl; wherein the heteroaryl contains one heteroatom O, and wherein the heteroaryl carries zero, one or two substituents (R56)0, as defined and preferably defined herein, wherein o is 0, 1 or 2. According to one specific embodiment, o is 0. According to a further embodiment, o is 1 or 2. Particular embodiments thereof are listed in Table P56.
According to one embodiment, R5 and R6 together with the carbon atoms to which they are bound form a five-membered heteroaryl; wherein the heteroaryl contains one or two
heteroatoms selected from N, O and S, and wherein the heteroaryl carries zero, one or two substituents (R56)0, as defined and preferably defined herein, wherein o is 0, 1 or 2. According to one specific embodiment, o is 0. According to a further embodiment, o is 1 or 2. Particular embodiments thereof are listed in Table P56.
According to one embodiment, R5 and R6 together with the carbon atoms to which they are bound form a five-membered heteroaryl; wherein the heteroaryl contains one or two
heteroatoms N, and wherein the heteroaryl carries zero, one or two substituents (R56)0, as defined and preferably defined herein, wherein o is 0, 1 or 2. According to one specific embodiment, o is 0. According to a further embodiment, o is 1 or 2. Particular embodiments thereof are listed in Table P56.
According to one embodiment, R5 and R6 together with the carbon atoms to which they are bound form a five-membered heteroaryl; wherein the heteroaryl contains one or two
heteroatoms selected from O and S, and wherein the heteroaryl carries zero, one or two substituents (R56)0, as defined and preferably defined herein, wherein o is 0, 1 or 2. According to one specific embodiment, o is 0. According to a further embodiment, o is 1 or 2. Particular embodiments thereof are listed in Table P56.
According to one embodiment, R5 and R6 together with the carbon atoms to which they are bound form a five-membered heteroaryl; wherein the heteroaryl contains one heteroatom S, and wherein the heteroaryl carries zero, one or two substituents (R56)0, as defined and preferably defined herein, wherein o is 0, 1 or 2. According to one specific embodiment, o is 0. According to a further embodiment, o is 1 or 2.
According to one embodiment, R5 and R6 together with the carbon atoms to which they are bound form a five-membered heteroaryl; wherein the heteroaryl contains one heteroatom O, and wherein the heteroaryl carries zero, one or two substituents (R56)0, as defined and preferably defined herein, wherein o is 0, 1 or 2. According to one specific embodiment, o is 0. According to a further embodiment, o is 1 or 2. Particular embodiments thereof are listed in Table P56.
According to a further embodiment, R5 and R6 together with the carbon atoms to which they are bound form a six-membered heteroaryl; wherein the heteroaryl contains one or two heteroatoms selected from N, O and S, and wherein the heteroaryl carries zero, one or two substituents
(R56)o, as defined and preferably defined herein, wherein o is 0, 1 or 2. According to one specific embodiment, o is 0. According to a further embodiment, o is 1 or 2. Particular embodiments thereof are listed in Table P56.
According to a further embodiment, R5 and R6 together with the carbon atoms to which they are bound form a six-membered heteroaryl; wherein the heteroaryl contains one or two heteroatoms N, and wherein the heteroaryl carries zero, one or two substituents (R56)0, as defined and preferably defined herein, wherein o is 0, 1 or 2. According to one specific embodiment, o is 0. According to a further embodiment, o is 1 or 2. Particular embodiments thereof are listed in Table P56.
According to the invention, there can be zero, one, two or three R56 present, namely for o is 0, 1 , 2 or 3.
According to one embodiment, o is 0.
According to a further embodiment, o is 1.
According to a further embodiment, o is 2 or 3. According to one specific embodiment thereof, o is 2, according to a further specific embodiment, o is 3.
For every R56 that is present in the inventive compounds, the following embodiments and preferences apply independently of the meaning of any other R56 that may be present in the ring. Furthermore, the particular embodiments and preferences given herein for R56 apply independently for each of o=1 , o=2 and o=3.
According to one specific embodiment, R56 is halogen, in particular F, CI, Br or I, more specifically F, CI or Br, in particular F or CI.
According to still another embodiment of formula I, R56 is F.
According to still another embodiment of formula I, R56 is CI.
According to still another embodiment of formula I, R56 is Br.
According to a further specific embodiment, R56 is OH.
According to a further specific embodiment, R56 is CN.
According to a further specific embodiment, R56 is NO2.
According to still another embodiment of formula I, R56 is SH.
According to still another embodiment of formula I, R56 is NH2.
According to still another embodiment of formula I, R56 is , NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, ,
NH(C(=0)(Ci-C4-alkyl), N(C(=0)(Ci-C4-alkyl)2, wherein Ci-C4-alkyl is CH3, C2H5, n-propyl, i-pro- pyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
According to a further specific embodiment of formula I, R56 is NH-S02-RX such as NH-SO2-CH3, NH-SO2-CH2-CH3, NH-SO2-CF3 or NH-SO2-TS.
According to a further specific embodiment of formula I, R56 is CH(=0), C(=0)Ci-C6-alkyl,
C(=0)0(Ci-C6-alkyl) or C(=0)NH(Ci-C6-alkyl), wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n- butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
According to a further specific embodiment of formula I, R56 is CR =NOR such as C(CH3)=NOCH3, C(CH3)=NOCH2CH3 or C(CH3)=NOCF3.
According to a further specific embodiment, R56 is Ci-C6-alkyl, in particular Ci-C4-alkyl, such as CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl., in particular CH3. According to a further specific embodiment, R56 is Ci-C6-halogenalkyl, in particular C1-C4- halogenalkyl, such as CF3, CCI3, FCH2, CICH2, F2CH, CI2CH, CF3CH2, CCI3CH2 or CF2CHF2. According to still a further embodiment, R56 is C2-C6-alkenyl, in particular C2-C4-alkenyl, such as CH=CH2 or CH2 CH=CH2.
According to still another embodiment of formula I R56 is C3-C6-cycloalkyl, in particular cyclopro- pyl.
According to still another embodiment of formula I, R56 is C3-C6-halogencycloalkyl. In a special embodiment R1 is fully or partially halogenated cyclopropyl.
According to still a further embodiment, R56 is C3-C6-cycloalkyl-C2-C6-alkenyl, in particular C3-C6- cycloalkyl-C2-C4-alkenyl, more specifically C3-C6-cycloalkyl-C2-C3-alkenyl, such as C3H5- CH=CH2.
According to a further specific embodiment, R56 is C2-C6-halogenalkenyl, in particular C2-C4-hal- ogenalkenyl, more specifically C2-C3-halogenalkenyl such as CH=CHF, CH=CHCI, CH=CF2, CH=CCI2, CH2CH=CHF, CH2CH=CHCI, CH2CH=CF2, CH2CH=CCI2. CH2CF=CF2,
CH2CCI=CCI2. CF2CF=CF2 or CCI2CCI=CCI2.
According to still a further embodiment, R56 is C2-C6-alkynyl, in particular C2-C4-alkynyl, more specifically C2-C3-alkynyl, such as C≡CH.
According to still a further embodiment, R56 is C2-C6-halogenalkynyl, in particular C2-C4-halogen- alkynyl, more specifically C2-C3-halogenalkynyl.
According to a further specific embodiment, R56 is Ci-C6-alkoxy, in particular Ci-C4-alkoxy, more specifically Ci-C2-alkoxy such as OCH3 or OCH2CH3.
According to a further specific embodiment, R56 is Ci-C6-halogenalkoxy, in particular C1-C4- halogenalkoxy, more specifically Ci-C2-halogenalkoxy such as OCF3, OCHF2, OCH2F, OCCI3, OCHCI2, OCH2CI and OCF2CHF2, in particular OCF3, OCHF2 and OCF2CHF2.
According to a further specific embodiment of formula I, R56 is C2-C6-alkenyloxy, in particular C2- C4-alkenyloxy, more specifically Ci-C2-alkenyloxy such as OCH=CH2, OCH2CH=CH2.
According to a further specific embodiment of formula I, R56 is C2-C6-alkynyloxy, in particular C2- C4-alkynyloxy, more specifically Ci-C2-alkynyloxy such as OC CH
According to a further specific embodiment of formula I, R56 is S(0)n-Ci-C6-alkyl, wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl and n is 1 , 2 or 3. According to a further specific embodiment of formula I, R56 is S(0)n-Ci-C6-halogenalkyl, wherein halogenalkyl is CF3 or CHF2 and n is 1 , 2 or 3.
According to still another embodiment of formula I, R56 is a partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered heterocycle, in particular three-, four-, five- or six-membered, wherein the heterocycle contains one, two, three or four heteroatoms selected
from N, O and S, and wherein the heterocycle is unsubstituted or substituted with substituents R56b as defined below. According to one embodiment thereof, the heterocycle is unsubstituted.
According to still another embodiment of formula I, R56 is a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered heterocycle, in particular three-, four-, five- or six-mem- bered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the heterocycle is unsubstituted or substituted with substituents R56b as defined below. According to one embodiment thereof, the heterocycle is unsubstituted.
According to still another embodiment of formula I, in the embodiments of R56 described above, the heterocycle contains preferably one, two or three, more specifically one or two heteroatoms selected from N, O and S. More specifically, the hetereocycle contains one heteroatom selected from N, O and S. In particular, the heterocycle contains one or two, in particular one O.
According to one embodiment, R56 is a 4-membered saturated heterocycle which contains 1 or 2 heteroatoms, in particular 1 heteroatom, from the group consisting of N, O and S, as ring members. According to one embodiment, the heterocycle contains one O as heteroatom. For example, the formed heterocycle is oxetane. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R56b. According to still another embodiment of formula I, it is substituted with R56b.
According to still another embodiment of formula I, R56 is a 5-membered saturated heterocycle which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S, as ring members. According to one embodiment, the heterocycle contains one O as heteroatom. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R56b. According to still another embodiment of formula I, it is substituted with R56 .
According to still another embodiment of formula I, R56 is a 6-membered saturated heterocycle which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S as ring members. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R56b. According to still another embodiment of formula I, it is substituted with R56b. According to one specific embodiment thereof, said 6-membered saturated heterocycle contains 1 or 2, in particular 1 , heteroatom(s) O. According to one
embodiment thereof, the respective 6-membered heterocycle is unsubstituted, i.e. it does not carry any substituent R56b. According to still another embodiment of formula I, it is substituted with R56 .
According to still another embodiment of formula I, R56 is phenyl-Ci-C6-alkyl, such as phenyl- CH2, wherein the phenyl moiety in each case is unsubstituted or substituted with one, two or three identical or different groups R56b which independently of one another are selected from halogen, Ci-C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl and Ci-C2-halogenalkoxy, in particular CN, F, CI, Br, CH3, OCH3, CHF2, CF3 OCHF2, and OCF3.
According to still a further specific embodiment, R56 is unsubstituted phenyl or phenyl that is substituted with one, two, three or four R56b, as defined and preferably herein. In particular, R56 is unsubstituted phenyl or phenyl that is substituted with one, two, three or four R56b, as defined herein. In one embodiment R56 is unsubstituted phenyl.
According to still another embodiment of formula I, R56 is a 5-membered heteroaryl such as pyrrol-1 -yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1 -yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1 -yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1 ,2,4-triazolyl-1 -yl, 1 ,2,4- triazol-3-yl 1 ,2,4-triazol-5-yl, 1 ,2,4-oxadiazol-3-yl, 1 ,2,4-oxadiazol-5-yl and 1 ,2,4-thiadiazol-3-yl, 1 ,2,4-thiadiazol-5-yl.
According to still another embodiment of formula I, R56 is a 6-membered heteroaryl, such as pyr- idin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, py- rimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl.
According to one further embodiment, R56 is in each case independently selected from halogen, CN, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyl, S(0)n-Ci-C6-alkyl, three-, four-, five- or six-membered saturated or partially unsaturated heterocycle, five- or six-membered heteroaryl and phenyl; wherein the heterocycle or heteroaryl contains one, two or three heteroatoms selected from N, O and S; and wherein the acyclic moieties of R56 are not further substituted or carry one, two, three or up to the maximum possible number of identical or different groups R56a as defined and preferably defined herein, and wherein the heterocyclic, alicyclic, phenyl and heteroaryl moieties of R56 are not further substituted or carry one, two, three, four, five or up to the maximum number of identical or different groups R56b as defined and preferably defined herein.
According to one further embodiment, R56 is in each case independently selected from halogen, CN, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, C3-C6- alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyl, S(0)n-Ci-C6-alkyl, three-, four-, five- or six-membered saturated or partially unsaturated heterocycle, five- or six-membered heteroaryl and phe- nyl; wherein the heterocycle or heteroaryl contains one, two or three heteroatoms selected from N, O and S; and wherein the acyclic moieties of R56 are not further substituted or carry one, two, three or up to the maximum possible number of identical or different groups R56a as defined and preferably defined herein, and wherein the heterocyclic, alicyclic, phenyl and heteroaryl moieties of R56 are not further substituted or carry one, two, three, four, five or up to the maximum num- ber of identical or different groups R56b as defined and preferably defined herein. Accordingto one specific embodiment, the acyclic and cyclic moieties of R56 are not further substituted, according to another embodiment, the acyclic moieties of R56 carry one, two, three or four identical or different groups R56a as defined and preferably defined herein.
According to a further embodiment, R56 is in each case independently selected from halogen, CN, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyl and S(0)n-Ci-C6-alkyl, wherein the acyclic moieties of R56 are not further substituted or carry one, two, three or up to the maximum possible number of identical or different groups R56a as defined and preferably defined herein, and wherein the cycloalkyi moieties of R56 are not further substituted or carry one, two, three, four, five or up to the maximum number of identical or different groups R56b as defined and preferably defined herein.
According to a further embodiment, R56 is in each case independently selected from halogen, CN, Ci-C6-alkyl, , Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, Ci-C6-halo- genalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkyl and S(0)n-Ci-C6-alkyl, wherein
the acyclic moieties of R56 are not further substituted or carry one, two, three or up to the maximum possible number of identical or different groups R56a as defined and preferably defined herein, and wherein the cycloalkyl moieties of R56 are not further substituted or carry one, two, three, four, five or up to the maximum number of identical or different groups R56b as defined and preferably defined herein. Accordingto one specific embodiment, the acyclic and cyclic moieties of R56 are not further substituted, according to another embodiment, the acyclic moieties of R56 carry one, two, three or four identical or different groups R56a as defined and preferably defined herein.
According to still a further embodiment, R56 is in each case independently selected from halo- gen, Ci-C6-alkyl and Ci-C6-alkoxy, wherein the acyclic moieties of R56 are not further substituted or carry one, two, three or up to the maximum possible number of identical or different groups R56a defined and preferably defined herein.
According to still a further embodiment, R56 is in each case independently selected from CN, halogen, Ci-C6-alkyl, Ci-C6-halogenalkyl, Ci-C6-alkoxy and Ci-C6-halogenalkoxy, wherein the acyclic moieties of R56 are not further substituted or carry one, two, three or up to the maximum possible number of identical or different groups R56a defined and preferably defined herein. Accordingto one specific embodiment, the acyclic and cyclic moieties of R56 are not further substituted, according to another embodiment, the acyclic moieties of R56 carry one, two, three or four identical or different groups R56a as defined and preferably defined herein.
R56a are the possible substituents for the acyclic moieties of R56. R56a is independently selected from halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6- halogencycloalkyl, C3-C6-halogencycloalkenyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, five- or six- membered heteroaryl, phenyl and phenoxy, wherein the heteroaryl and phenyl group is unsubstituted or carries one, two, three, four or five substituents R56a' selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and C1-C4- halogenalkoxy.
According to one embodiment R56a is independently selected from halogen, Ci-C6-alkoxy, C3- C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C4-halogenalkoxy. Specifically, R56a is
independently selected from F, CI, Br, I, Ci-C2-alkoxy, cyclopropyl, 1 -F-cyclopropyl, 1 -CI- cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1 -Cl2-cyclopropyl and Ci-C2-halogenalkoxy.
According to a further embodiment, R56a is independently halogen, in particular selected from F, CI, Br and I, more specifically F, CI and Br.
R56b are the possible substituents for the cycloalkyl, heterocyclyl, heteroaryl and phenyl moieties of R56. R56b according to the invention is independently selected from halogen, OH, CN, C1-C4- alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4- halogenalkoxy and Ci-C6-alkylthio.
According to one embodiment thereof R56b is independently selected from halogen, CN, C1-C4- alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl and Ci-C4-halogenalkoxy, in particular halogen, C1-C4- alkyl and Ci-C4-alkoxy. Specifically, R56b is independently selected from F, CI, CN, CH3, OCH3 and halogenmethoxy.
Particularly preferred embodiments of R5 and R6, optionally substituted with (R56)0, according to
the invention are in Table P56 below, wherein each line of lines P56-1 to P56-82 corresponds to one particular embodiment of the invention, wherein P56-1 to P56-82 are also in any combination with one another a preferred embodiment of the present invention. Thereby, the positions of the heteroaryls marked with "#" represents the connection points (carbon atoms 5' and 6' in formula I) with the remaining skeleton of the compounds of formula I:
Table P56:
A is according to one embodiment O.
A is according to one further embodiment S. B is according to one embodiment is -C(R7R8)-S-.
B is according to one further embodiment C(R7R8)-S(0)-.
B is according to one further embodiment C(R7R8)-S(0)2-.
B is according to one further embodiment -C(R7R8)-0-.
B is according to one further embodiment -C(R7R8)-NR9-.
B is according to one further embodiment -C(R7R8)-C(=0)-.
B is according to one further embodiment -C(R7R8)-C(=S)-.
B is according to one further embodiment C(R7)=N-.
R7 is independently selected from H, halogen, OH, CN, N02, SH, d-Ce-alkylthio, NH2, NH(Ci- C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-hal- ogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, C2-C6- alkenyloxy, C2-C6-alkynyloxy, CH(=0), C(=0)Ci-C6-alkyl, C(=0)0(Ci-C6-alkyl), C(=0)N H(Ci-C6- alkyl), C(=0)N(Ci-C6-alkyl)2, CR -NOR", a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, a five- or six-membered heteroaryl, aryl and phenoxy; wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(=0) and C(=S), and wherein the heterocycle and the heteroaryl contain independently one, two, three or four heteroatoms selected from N, O and S; and wherein R' and R" are independently selected from H, Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl or aryl; and wherein R' and R" are independently unsubstituted or substituted with R'" which is independently selected from halogen, OH, CN , N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci- C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2- C6-alkynyl, C2-C6-halogenalkynyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, C3-C6-cycloalkyl, C3-C6- halogencycloalkyl and phenyl;
wherein Rx is as defined above;
wherein the acyclic moieties of R7 are independently not further substituted or carry one, two, three or up to the maximum possible number of identical or different groups R7a, which independently of one another are selected from:
R7a halogen, OH , CN, N02, SH, NH2, N H(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkoxy, Ci-C4-halogenalkoxy, C3-C6-cycloalkyl, C3-C6- halogencycloalkyl, Ci-C6-alkylthio, Ci-C6-halogenalkylthio, S(0)n-Ci-C6-alkyl, S(0)n-aryl, CH(=0), C(=0)Ci-C6-alkyl, C(=0)0(Ci-C6-alkyl), C(=0)N H(Ci-C6-alkyl), C(=0)N(Ci-C6-alkyl)2, CR'=NOR", a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- or heterocycle, an aryl, phenoxy and a five-, six- or ten-membered heteroaryl, wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(=0) and C(=S), and wherein the heterocycle and the heteroaryl contains independently one, two, three or four heteroatoms selected from N, O and S; wherein the carbo-, heterocyclic, heteroaryl and phenyl groups are independently un- substituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH , CN, N02, SH, NH2, N H(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkylthio, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-
alkoxy, Ci-C4-halogenalkoxy, and S(0)n-Ci-C6-alkyl; and wherein Rx, R' and R" are as defined above; n is 0, 1 , 2; and
wherein the carbocclic, heterocyclic, heteroaryl and aryl moieties of R7 are independently unsubstituted or substituted with identical or different groups R7b, which independently of one an- other are selected from:
R7b halogen, OH , CN , N02, SH , N H2, N H(Ci-C4-alkyl), N (Ci-C4-alkyl)2, N H(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, N H-S02-Rx, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloal- kyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, Ci-C6-halogenalkylthio, S(0)n-Ci-C6-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy; and wherein Rx and n are as defined above.
According to one embodiment of formula I, R7 is independently selected from CN , Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C3-C6-cycloalkenyl, C2-C6-alkynyl, C2- Ce-halogenalkynyl, C3-C6-cycloalkynyl, CH(=0), C(=0)Ci-C6-alkyl, C(=0)0(Ci-C6-alkyl),
CR'=NOR" , C3-C6-halogencycloalkyl, a saturated three-, four-, five-, six-, membered carbo- or heterocycle, a five- or six-membered heteroaryl, aryl and Ci-C6-alkyl substituted with CN , C1-C6- alkoxy, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, S(0)n-Ci-C6-alkyl, S(0)n-Ci-C6-halogenalkyl, N H- S02-Rx, N(Ci-C6-alkyl)2, CH(=0), C(=0)Ci-C6-alkyl, C(=0)0(Ci-C6-alkyl), a saturated three-, four-, five-, six-, membered carbo- or heterocycle, aryl; wherein Rx, R' and R" are defined below; and wherein the acyclic moieties of R7 are unsubstituted or substituted with identical or different groups R7a as defined below and wherein wherein the carbo-, heterocycle and heteroaryl and aryl moieties are unsubstituted or substituted with substituents R7b as defined below.
According to one embodiment of formula I, R7 is selected from Ci-C6-alkyl, C2-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C3-C6-cycloalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, Cs-Ce-cycloalkynyl, CH(=0), C(=0)C2-C6-alkyl, C(=0)0(C2-C6-alkyl), CR'=NOR", C3-C6-cycloal- kyl, C3-C6-halogencycloalkyl, Ci-C6-alkyl-five- and six-membered heteroaryl or aryl; wherein the aryl is unsubstituted or substituted with halogen or Ci-C6-halogenalkyl; wherein R' and R" are defined below; and wherein the acyclic moieties of R7 are unsubstituted or substituted with iden- tical or different groups R7a as defined below and wherein wherein the carbocycle, heterocycle and heteroaryl and aryl moieties are unsubstituted or substituted with substituents R7b as defined below.
According to one embodiment of formula I, R7 is selected from Ci-C6-alkyl substituted with CN , d-Ce-alkoxy, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, S(0)n-Ci-C6-alkyl, N H-S02-Rx, N(Ci-C6-al- kyl)2, CH(=0), C(=0)Ci-C6-alkyl, C(=0)0(Ci-C6-alkyl), a saturated three-, four-, five-, six-, membered carbo- or heterocycle, aryl; wherein Rx is defined below; and wherein the acyclic moieties of R7 are unsubstituted or substituted with identical or different groups R7a as defined below and wherein wherein the carbocycle, heterocycle and heteroaryl and aryl moieties are unsubstituted or substituted with substituents R7b as defined below.
According to still another embodiment of formula I, R7 is selected from Ci-C6-alkyl, Ci-C6-halo- genalkyl, CN , C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3-C6-
cycloalkyl, C3-C6-halogencycloalkyl, Ci-C6-alkylaryl, Ci-C6-alkylheteroaryl, phenyl, pyridine, py- rimidine, thiophene, imidazole, triazol, oxadiazol wherein the acyclic moieties of R7 are unsubstituted or substituted with identical or different groups R7a as defined below and wherein wherein the carbocycle, heterocycle, heteroaryl and aryl moieties are unsubstituted or substituted with substituents R7b as defined below.
According to still another embodiment of formula I, R7 is H.
According to another embodiment of formula I, R7 is F
According to another embodiment of formula I, R7 is CI
According to another embodiment of formula I, R7 is Br.
According to still another embodiment of formula I, R7 is OH.
According to still another embodiment of formula I, R7 is CN.
According to still another embodiment of formula I, R7 is NO2.
According to still another embodiment of formula I, R7 is SH.
According to still another embodiment of formula I, R7 is Ci-C6-alkylthio, such as SCH3, SC2H5, Sn-propyl, Si-propyl, Sn-butyl, Si-butyl, Stert-butyl, Sn-pentyl, Si-pentyl, CH2SCH3 or
According to still another embodiment of formula I, R7 is Ci-C6-halogenalkylthio, such as SCF3, SCCI3, CH2SCF3 or CH2SCF3.
According to still another embodiment of formula I, R7 is selected from Ci-C6-alkyl, Ci-C6-halo- genalkyl, phenyl, halogenphenyl and three-, four-, five- or six-membered carbo- and heterocycle, wherein the carbo- and heterocycle is unsubstituted or is substituted with substituents R7b as defined below. According to one embodiment thereof, the carbocycle is unsubstituted. In a particular embodiment, R7 is selected from Ci-C6-halogenalkyl, phenyl-Chb, halogenphenyl- CH2, phenyl, halogenphenyl and three-, four-, five- or six-membered carbo- and heterocycle, wherein the carbo- and heterocycle is unsubstituted or is substituted with substituents R7b as defined below.
According to still another embodiment of formula I, R7 is selected from Ci-C6-alkyl, Ci-C6-halo- genalkyl, phenyl, halogenphenyl and three-, four-, five- or six-membered carbo- and heterocycle, wherein the carbo- and heterocycle is unsubstituted or substituted withsubstituents R7b as defined below. According to one embodiment thereof, the carbo- and heterocycle is unsubstituted. In a particular embodiment, R7 is selected from substituted Ci-C6-halogenalkyl, phenyl, halogenphenyl and three-, four-, five- or six-membered carbo- and heterocycle, wherein the carbo- and heterocycle is unsubstituted or substituted withsubstituents R7b as defined below.
According to another embodiment of formula I, R7 is selected from Ci-C6-alkyl, Ci-C6-halogen- alkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloal- kyl, C3-C6-halogencycloalkyl, Ci-C6-alkylaryl, six-membered heteroaryl or aryl which is unsubstituted or substituted with halogen or Ci-C6-halogenalkyl, and wherein the acyclic moieties of R7 are unsubstituted or substituted with identical or different groups R7a as defined below and wherein wherein the carbocycle, heterocycle and heteroaryl and aryl moieties are unsubstituted
or substituted with substituents R7b as defined below.
According to still another embodiment of formula I, R7 is selected from Ci-C6-alkyl, Ci-C6-halo- genalkyl, CN, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3-C6- cycloalkyl, C3-C6-halogencycloalkyl, Ci-C6-alkylaryl, phenyl, pyridine, pyrimidine, thiophene, im- idazole, triazol, oxadiazol wherein the acyclic moieties of R7 are unsubstituted or substituted with identical or different groups R7a as defined below and wherein wherein the carbocycle, heterocycle and heteroaryl and aryl moieties are unsubstituted or substituted with substituents R7b as defined below.
According to still another embodiment of formula I, R7 is Ci-C6-alkyl such as CH3, C2H5, n-pro- pyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
According to still another embodiment of formula I, R7 is Ci-C6-alkyl such as CH3, C2H5, n-pro- pyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
According to still another embodiment of formula I, R7 is Ci-C6-alkyl such as CH3.
According to still another embodiment of formula I, R7 is Ci-C6-alkyl such as C2H5.
According to still another embodiment of formula I, R7 is Ci-C6-alkyl such as CH3, C2H5, n-pro- pyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl which is substituted with at least one group R7a, which independently of one another are selected from:
R7a halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkoxy, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, Ci-C6- halogenalkylthio, S(0)n-Ci-C6-alkyl, S(0)n-aryl, CH(=0), C(=0)Ci-C6-alkyl, C(=0)0(Ci-C6-alkyl), C(=0)NH(Ci-C6-alkyl), C(=0)N(Ci-C6-alkyl)2, CR'=NOR", a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, a five- or six-membered heteroaryl, an aryl or phenoxy, wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(=0) and C(=S), and wherein the heterocycle and heteroaryl contains independently one, two, three or four heteroatoms selected from N, O and S; wherein the carbocyclic, heterocyclic, heteroaryl and phenyl groups are independently unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH, CN, NO2, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkylthio, Ci- C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy, and S(0)n-Ci-C6-alkyl.
According to still another embodiment of formula I, R7 is CH3 is substituted with at least one group R7a, which independently of one another are selected from:
R7a halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkoxy, Ci-C4-halogenalkoxy, d-Ce-alkylthio, Ci-C6- halogenalkylthio, S(0)n-Ci-C6-alkyl, S(0)n-aryl, CH(=0), C(=0)Ci-C6-alkyl, C(=0)0(Ci-C6-alkyl), C(=0)NH(Ci-C6-alkyl), C(=0)N(Ci-C6-alkyl)2, CR'=NOR", a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, a five- or six-membered heteroaryl an aryl or phenoxy, wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(=0) and C(=S), and wherein the heterocycle and heteroaryl contains independently one, two, three or four heteroatoms selected from N, O and S; wherein the carbocyclic, heterocyclic, heteroaryl and phenyl groups are independently unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH, CN, NO2, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkylthio, Ci-
C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy, and S(0)n-Ci-C6-alkyl.
According to still another embodiment of formula I , R7 is C2H5 is substituted with at least one group R7a, which independently of one another are selected from:
R7a halogen, OH, CN, N02, SH, NH2, N H(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkoxy, Ci-C4-halogenalkoxy, d-C6-alkylthio, Ci-C6- halogenalkylthio, S(0)n-Ci-C6-alkyl, S(0)n-aryl, CH(=0), C(=0)Ci-C6-alkyl, C(=0)0(Ci-C6-alkyl), C(=0)NH(Ci-C6-alkyl), C(=0)N(Ci-C6-alkyl)2, CR'=NOR"a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, a five- or six-membered heteroaryl an aryl or phenoxy, wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(=0) and C(=S), and wherein the heterocycle and heteroaryl contains independently one, two, three or four heteroatoms selected from N, O and S; wherein the carbocyclic, heterocyclic, heteroaryl and phenyl groups are independently unsubstituted or carry one, two, three, four or five substit- uents selected from the group consisting of halogen, OH, CN, NO2, SH, NH2, N H(Ci-C4-alkyl), N(Ci-C4-alkyl)2, N H(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkylthio, Ci- C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy, and S(0)n-Ci-C6-alkyl.
According to still another embodiment of formula I , R7 is CH2CN.
According to still another embodiment of formula I , R7 is CH2OH.
According to still another embodiment of formula I , R7 is Ci-C6-halogenalkyl, in particular C1-C4- halogenalkyl, more specifically Ci-C2-halogenalkyl, such as CF3, CC , FCH2, CICH2, F2CH, C CH, CF3CH2, CCI3CH2 or CF2CHF2.
According to still another embodiment of formula I , R7 is CH2F.
According to still another embodiment of formula I , R7 is CHF2.
According to still another embodiment of formula I , R7 is CF3.
According to still a further embodiment of formula I , R7 is C2-C6-alkenyl, in particular C2-C4-alk- enyl, such as CH=CH2, CH2CH=CH2 or C(CH3)C=CH2.
According to a further specific embodiment of formula I , R7 is C2-C6-halogenalkenyl, in particular C2-C4-halogenalkenyl, more specifically C2-C3-halogenalkenyl such as CH=CHF, CH=CHCI, CH=CF2, CH=CCI2, CF=CF2, CCI=CCI2, CH2CH=CHF, CH2CH=CHCI, CH2CH=CF2,
CH2CH=CCI2, CH2CF=CF2, CH2CCI=CCI2, CF2CF=CF2 or CCI2CCI=CCI2.
According to still a further embodiment of formula I , R7 is C2-C6-cycloalkenyl, in particular C2-C4- cycloalkenyl, such as CH=CH2-cPr.
According to still a further embodiment of formula I , R7 is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as C CH, C C-CI,
CH2- C≡CH, CH2-C≡CCI or CH2- C≡C-CH3.
According to still a further embodiment of formula I , R7 is C2-C6-cycloalkynyl in particular C2-C4- cycloalkynyl, such as C C-cPr.
According to a further specific embodiment of formula I , R7 is Ci-C6-alkoxy, in particular C1-C4- alkoxy, more specifically Ci-C2-alkoxy such as OCH3, CH2CH3 or CH2OCH3.
According to a further specific embodiment of formula I , R7 is Ci-C6-alkyl-Ci-C6-alkoxy, in
particular Ci-C4-alkyl-Ci-C4-alkoxy, more specifically Ci-C2-alkyl-Ci-C2-alkoxy, such as
According to a further specific embodiment of formula I, R7 is C2-C6-alkenyloxy, in particular C2- C4-alkenyloxy, more specifically Ci-C2-alkenyloxy such as OCH=CH2, OCH2CH=CH2
OC(CH3)CH=CH2, CH2OCH=CH2, or CH2OCH2CH=CH2.
According to a further specific embodiment of formula I, R7 is C2-C6-alkynyloxy, in particular C2- C4-alkynyloxy, more specifically Ci-C2-alkynyloxy such as OC CH, OChbC CH or ChbOC CH
According to a further specific embodiment of formula I, R7 is Ci-C6-halogenalkoxy, in particular Ci-C4-halogenalkoxy, more specifically Ci-C2-halogenalkoxy such as OCF3, OCHF2, OCH2F, OCCIs, OCHC or OCH2CI, in particular OCF3, OCHF2, OCCI3 or OCHCI2.
According to a further specific embodiment of formula I, R7 is Ci-C6-alkyl-Ci-C6-halogenalkoxy, in particular Ci-C4-alkyl-Ci-C4-halogenalkoxy, more specifically Ci-C2-alkyl-Ci-C2-halogenalkoxy such as CH2OCF3, CH2OCHF2, CH2OCH2F, CH2OCCI3, CH2OCHCI2 or CH2OCH2CI, in particular CH2OCF3, CH2OCHF2, CH2OCCI3 or CH2OCHCI2.
According to a further specific embodiment of formula I, R7 is CH(=0), C(=0)Ci-C6-alkyl,
C(=0)0(Ci-C6-alkyl), C(=0)N H(Ci-C6-alkyl) or C(=0)N(Ci-C6-alkyl)2, wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
According to a further specific embodiment of formula I, R7 is Ci-C4-alkyl-CH(=0), Ci-C4-alkyl- C(=0)Ci-C6-alkyl, Ci-C4-alkyl-C(=0)0(Ci-C6-alkyl), Ci-C4-alkyl-C(=0)NH(Ci-C6-alkyl) or Ci-C4- alkyl-C(=0)N(Ci-C6-alkyl)2, especially CH2CH(=0), CH2C(=0)Ci-C6-alkyl, CH2C(=0)0(Ci-C6- alkyl), CH2C(=0)NH(Ci-C6-alkyl) or CH2C(=0)N(Ci-C6-alkyl)2 wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
According to a further specific embodiment of formula I, R7 is CR'=NOR" such as
C(CH3)=NOCH3, C(CH3)=NOCH2CH3 or C(CH3)=NOCF3.
According to a further specific embodiment of formula I, R7 is Ci-C6-alkyl-NH(Ci-C4-alkyl) or Ci- C6-alkyl-N(Ci-C4-alkyl)2, wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
According to a further specific embodiment of formula I, R7 is Ci-C6-alkyl-S(0)n-Ci-C6-alkyl, wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl and n is 1 , 2 or 3.
According to a further specific embodiment of formula I, R7 is Ci-C6-alkyl-S(0)n-Ci-C6- halogenalkyl, wherein halogenalkyl is CF3 or CHF2 and n is 1 , 2 or 3.
According to a further specific embodiment of formula I, R7 is Ci-C6-alkyl-S(0)n-aryl, wherein the aryl or phenyl moiety in each case is unsubstituted or substituted with identical or different groups R7b which independently of one another are selected from halogen, Ci-C2-alkyl, C1-C2- alkoxy, Ci-C2-halogenalkyl, Ci-C2-halogenalkoxy and S(0)n-Ci-C6-alkyl, in particular F, CI, Br, CH3, OCH3, CF3, CHF2, OCHF2, OCF3. According to one embodiment, R7 is unsubstituted phenyl. According to another embodiment, R7 is phenyl, that is substituted with one, two or three, in particular one, halogen, in particular selected from F, CI and Br, more specifically selected from F and CI.
According to a further specific embodiment of formula I , R7 is Ci-C6-alkyl-NH-S02-Rx wherein Rx is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted with one, two, three, four or five substituents Rx2 independently selected from Ci-C4-alkyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy, or Ci-C4-halogenalkoxy, such as CH2NHS02CF3 or
According to still another embodiment of formula I , R7 is selected from Ci-C6-alkyl which is substituted, a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle, in particular three-, four-, five- or six-membered, wherein the carbocycle is unsubstituted or substituted with substituents R7b as defined below. According to one embodiment thereof, the car- bocycle is unsubstituted.
According to one embodiment, R7 is selected from Ci-C6-alkyl, especially CH2 which is substituted with a 3-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I , it is substituted with R7b.
According to one embodiment, R7 is selected from Ci-C6-alkyl, especially CH2 which is substituted with a 4-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I, it is substituted with R7b.
According to one embodiment, R7 is selected from Ci-C6-alkyl, especially with CH2 optionally substituted CH2 which is substituted with a 5-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I , it is substituted with R7b.
According to one embodiment, R7 is selected from Ci-C6-alkyl, especially CH2 which is substituted with a 6-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I , it is substituted with R7b.
According to a further specific embodiment of formula I , R7 is Ci-C6-alkyl, especially CH2 substituted with a 4-membered saturated heterocyde which contains 1 or 2 heteroatoms, in particular 1 heteroatom, from the group consisting of N, O and S, as ring members. According to one embodiment, the heterocyde contains one O as heteroatom. For example, the formed heterocyde is oxetane. According to one embodiment thereof, the heterocyde is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I , it is substituted with R7b.
According to a further specific embodiment of formula I , R7 is Ci-C6-alkyl, especially CH2 substituted with a 5-membered saturated heterocyde which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S, as ring members. According to one embodiment, the heterocyde contains one O as heteroatom. According to one embodiment thereof, the heterocyde is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I , it is substituted with R7b.
According to a further specific embodiment of formula I , R7 is Ci-C6-alkyl, especially CH2 subsitited by a 6-membered saturated heterocyde which contains 1 , 2 or 3, in particular 1 or 2,
heteroatoms from the group consisting of N, O and S as ring members. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I, it is substituted with R7b. According to one specific embodiment thereof, said 6-membered saturated heterocycle contains 1 or 2, in particu- lar 1 , heteroatom(s) O. According to one embodiment thereof, the respective 6-membered heterocycle is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I, it is substituted with R7b.
According to a further specific embodiment of formula I, R7 is Ci-C6-alkyl, especially Chb substituted with a 5-membered saturated heterocycle which contains one N as ring member and optionally one or two groups Chb are replaced by C(=0).
According to still another embodiment of formula I, R7 is a partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle, in particular three-, four-, five- or six-membered, wherein the carbocycle is unsubstituted or substituted with substituents R7b as defined below. According to one embodiment thereof, the carbocycle is unsubstituted.
According to still another embodiment of formula I, R7 is a partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, in particular three-, four-, five- or six-membered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the carbocycle and heterocycle are unsubstituted or substituted with substituents R7b as defined below. According to one embodiment thereof, the carbocycle or heterocycle is unsubstituted.
According to still a further embodiment, R7 is a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, in particular three-, four-, five- or six-membered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the carbocycle and heterocycle are unsubstituted or substituted with substit- uents R7b as defined below. According to one embodiment thereof, the carbocycle or heterocycle is unsubstituted.
According to still another embodiment of formula I, R7 is a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle, in particular three-, four-, five- or six-membered, wherein the carbocycle is unsubstituted or substituted with substituents R7b as defined below. According to one embodiment thereof, the carbocycle is unsubstituted.
According to one embodiment, R7 is a 3-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I, it is substituted with R7b.
According to one embodiment, R7 is a 3-membered saturated carbocycle, which is
unsubstituted such as cyclopropyl
According to one embodiment, R7 is a 3-membered saturated carbocycle, which is substituted with halogen, more specifically by F, such as C3H3F2.
According to one embodiment, R7 is a 3-membered saturated carbocycle, which is substituted with halogen. More specifically by CI, such as C3H3CI2.
According to one embodiment, R7 is a 4-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R7b.
According to still another embodiment of formula I, it is substituted with R7b.
According to one embodiment, R7 is a 5-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I, it is substituted with R7b.
According to one embodiment, R7 is a 6-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I, it is substituted with R7b.
According to still another embodiment of formula I, R7 is a partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered heterocycle, in particular three-, four-, five- or six-membered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the heterocycle is unsubstituted or substituted with substituents R7b as defined below. According to one embodiment thereof, the heterocycle is unsubstituted.
According to still another embodiment of formula I, R7 is a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered heterocycle, in particular three-, four-, five- or six-mem- bered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the heterocycle is unsubstituted or substituted with substituents R7b as defined below. According to one embodiment thereof, the heterocycle is unsubstituted.
According to still another embodiment of formula I, in the embodiments of R7 described above, the heterocycle contains preferably one, two or three, more specifically one or two heteroatoms selected from N, O and S. More specifically, the hetereocycle contains one heteroatom selected from N, O and S. In particular, the heterocycle contains one or two, in particular one O.
According to one embodiment, R7 is a 4-membered saturated heterocycle which contains 1 or 2 heteroatoms, in particular 1 heteroatom, from the group consisting of N, O and S, as ring members. According to one embodiment, the heterocycle contains one O as heteroatom. For exam- pie, the formed heterocycle is oxetane. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I, it is substituted with R7b.
According to still another embodiment of formula I, R7 is a 5-membered saturated heterocycle which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S, as ring members. According to one embodiment, the heterocycle contains one O as heteroatom. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I, it is substituted with R7 .
According to still another embodiment of formula I, R7 is a 6-membered saturated heterocycle which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S as ring members. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I, it is substituted with R7b. According to one specific embodiment thereof, said 6-membered saturated heterocycle contains 1 or 2, in particular 1 , heteroatom(s) O. According to one embodiment thereof, the respective 6-membered heterocycle is unsubstituted, i.e. it does not carry any substituent R7b. According to still another embodiment of formula I, it is substituted with R7b.
According to still another embodiment of formula I, R7 is phenyl-Ci-C6-alkyl, such as phenyl- CH2, wherein the phenyl moiety in each case is unsubstituted or substituted with one, two or three identical or different groups R7b which independently of one another are selected from CN, halogen, Ci-C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, Ci-C2-halogenalkoxy and S(0)n-Ci-C6- alkyl, in particular from CN, F, CI, Br, CH3, OCH3, CF3, CHF2, OCHF2, OCF3 and S(0)2CH3.
According to still another embodiment of formula I, R7 is aryl, in particular phenyl, wherein the aryl or phenyl moiety in each case is unsubstituted or substituted with identical or different groups R7b which independently of one another are selected from from CN, halogen, Ci-C2-al- kyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, Ci-C2-halogenalkoxy and S(0)n-Ci-C6-alkyl, in particular from CN, F, CI, Br, CH3, OCH3, CF3, CHF2, OCHF2, OCF3. According to one embodiment, R7 is unsubstituted phenyl. According to another embodiment, R7 is phenyl, that is substituted with one, two or three, in particular one, halogen, in particular selected from F, CI and Br, more specifically selected from F and CI.
According to still another embodiment of formula I, R7 is a 5-membered heteroaryl such as pyr- rol-1 -yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1 -yl, pyrazol- 3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1 -yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2- yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1 ,2,4-triazolyl-1 -yl, 1 ,2,4-triazol-3-yl 1 ,2,4-triazol-5-yl, 1 ,2,4-oxadiazol-3-yl, 1 ,2,4-oxadiazol-5-yl and 1 ,2,4-thiadiazol-3-yl, 1 ,2,4-thia- diazol-5-yl.
According to still another embodiment of formula I, R7 is a 6-membered heteroaryl, such as pyri- din-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, py- rimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl.
Particularly preferred embodiments of R7 according to the invention are in Table P7 below, wherein each line of lines P7-1 to P7-34 corresponds to one particular embodiment of the invention, wherein P7-1 to P7-34 are also in any combination with one another a preferred embodiment of the present invention. The connection point to the carbon atom, to which R7 is bound is marked with "#" in the drawings.
Table P7 (py = pyridyl):
No. R7 No. R7
P7-1 H P7-9 CH2CH(CH3)2
P7-2 CHs P7-10 C(CH3)3
P7-3 C2H5 P7-1 1 CH2CH2CH2CH2CH3
P7-4 ISO-C3H7 P7-12 CH2CH2CH(CH3)2
P7-5 CH2CH2CH3 P7-13 CF3
P7-6 CN P7-14 CHF2
P7-7 CH(CH3)2 P7-15 CHC
P7-8 CH2CH2CH2CH3 P7-16 CH2F
R8 is independently selected from H, halogen, OH, CN, N02, SH, d-Ce-alkylthio, NH2, NH(Ci- C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-Ce-alkyI, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-hal- ogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, C2-C6- alkenyloxy, C2-C6-alkynyloxy, CH(=0), C(=0)Ci-C6-alkyl, C(=0)0(Ci-C6-alkyl), C(=0)N H(Ci-C6- alkyl), C(=0)N(Ci-C6-alkyl)2, CR -NOR", a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, a five- or six-membered heteroaryl, aryl and phenoxy; wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(=0) and C(=S), and wherein the heterocycle and heteroaryl contain independently one, two, three or four heteroa- toms selected from N , O and S; and wherein R' and R" are independently selected from H , Ci- C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl
or aryl; and wherein R' and R" are independently unsubstituted or substituted with R'" which is independently selected from halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, d-Ce-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, C3-C6-cycloalkyl, C3-C6-halogency- cloalkyl and phenyl;
wherein Rx is as defined above;
wherein the acyclic moieties of R8 are independently not further substituted or carry one, two, three or up to the maximum possible number of identical or different groups R8a, which independently of one another are selected from:
R8a halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkoxy, Ci-C4-halogenalkoxy, C3-C6-cycloalkyl, C3-C6- halogencycloalkyl, Ci-C6-alkylthio, Ci-C6-halogenalkylthio, S(0)n-Ci-C6-alkyl, S(0)n-aryl, CH(=0), C(=0)Ci-C6-alkyl, C(=0)0(Ci-C6-alkyl), C(=0)NH(Ci-C6-alkyl), C(=0)N(Ci-C6-alkyl)2, CR'=NOR", a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- or heterocycle, a five-, six- or ten-membered heteroaryl, aryl or phenoxy, wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(=0) and C(=S), and wherein the heterocycle and heteroaryl contains independently one, two, three or four heteroatoms selected from N, O and S; wherein the carbo-, heterocyclic, heteroaryl and phenyl groups are independently unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4-alkyl),
alkyl)2, NH-S02-Rx, Ci-C6-alkylthio, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halo- genalkoxy, and S(0)n-Ci-C6-alkyl; and wherein Rx, R' and R" are as defined above; n is 0, 1 , 2; and
wherein the carbo-, heterocyclic, heteroaryl and phenyl moieties of R8 are independently unsubstituted or substituted with identical or different groups R8b, which independently of one another are selected from:
R8b halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloal- kyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, Ci-C6-halogenalkylthio,
S(0)n-Ci-C6-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy; and wherein Rx and n are as defined above.
According to one embodiment of formula I, R8 is selected from CN, Ci-C6-alkyl, Ci-C6-halogen- alkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C3-C6-cycloalkenyl, C2-C6-alkynyl, C2-C6-halogen- alkynyl, C3-C6-cycloalkynyl, CH(=0), C(=0)Ci-C6-alkyl, C(=0)0(Ci-C6-alkyl), CR'=NOR", C3-C6- halogencycloalkyl, a saturated three-, four-, five-, six-, membered carbo- or heterocycle, a five- or six-membered heteroaryl, aryl and phenoxy; and Ci-C6-alkyl substituted with CN, C1-C6- alkoxy, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, S(0)n-Ci-C6-alkyl, S(0)n-Ci-C6-halogenalkyl, NH- S02-Rx, N(Ci-C6-alkyl)2, CH(=0), C(=0)Ci-C6-alkyl, C(=0)0(Ci-C6-alkyl), a saturated three-, four-, five-, six-, membered carbo- or heterocycle, aryl; wherein Rx, R' and R" are defined below; and wherein the acyclic moieties of R8 are unsubstituted or substituted with identical or different
groups R8a as defined below and wherein wherein the carbo-, heterocycle and heteroaryl and aryl moieties are unsubstituted or substituted with substituents R8b as defined below.
According to one embodiment of formula I, R8 is selected from Ci-C6-alkyl, C2-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C3-C6-cycloalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, Cs-Ce-cycloalkynyl, CH(=0), C(=0)C2-C6-alkyl, C(=0)0(C2-C6-alkyl), CR'=NOR", C3-C6-cycloal- kyl, C3-C6-halogencycloalkyl, Ci-C6-alkyl-five- and six-membered heteroaryl ,a five- or six-mem- bered heteroaryl, aryl aryl and phenoxy, which is unsubstituted or substituted with halogen or Ci-C6-halogenalkyl; wherein R' and R" are defined below; and wherein the acyclic moieties of R3 are unsubstituted or substituted with identical or different groups R8a as defined below and wherein wherein the carbocycle, heterocycle and heteroaryl and aryl moieties are unsubstituted or substituted with substituents R8b as defined below.
According to one embodiment of formula I, R8 is selected from Ci-C6-alkyl substituted with CN, d-Ce-alkoxy, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, S(0)n-Ci-C6-alkyl, NH-S02-Rx, N(Ci-C6-al- kyl)2, CH(=0), C(=0)Ci-C6-alkyl, C(=0)0(Ci-C6-alkyl), a saturated three-, four-, five-, six-, mem- bered carbo- or heterocycle, aryl; wherein Rx is defined below; and wherein the acyclic moieties of R8 are unsubstituted or substituted with identical or different groups R8a as defined below and wherein wherein the carbocycle, heterocycle and heteroaryl and aryl moieties are unsubstituted or substituted with substituents R8b as defined below.
According to still another embodiment of formula I, R8 is H.
According to another embodiment of formula I, R8 is F
According to another embodiment of formula I, R8 is CI
According to another embodiment of formula I, R8 is Br.
According to still another embodiment of formula I, R8 is OH.
According to still another embodiment of formula I, R8 is CN.
According to still another embodiment of formula I, R8 is NO2.
According to still another embodiment of formula I, R8 is SH.
According to still another embodiment of formula I, R8 is Ci-C6-alkylthio, such as SCH3, SC2H5, Sn-propyl, Si-propyl, Sn-butyl, Si-butyl, Stert-butyl, Sn-pentyl, Si-pentyl, CH2SCH3 or
According to still another embodiment of formula I, R8 is Ci-C6-halogenalkylthio, such as SCF3, SCCI3, CH2SCF3 or CH2SCF3.
According to still another embodiment of formula I, R8 is selected from Ci-C6-alkyl, Ci-C6-halo- genalkyl or Ci-C6-alkyl which is substituted, Ci-C6-halogenalkyl, phenyl, halogenphenyl and three-, four-, five- or six-membered carbo- and heterocycle, wherein the carbo- and heterocycle is unsubstituted or is substituted with substituents R8b as defined below. According to one embodiment thereof, the carbocycle is unsubstituted. In a particular embodiment, R8 is selected from Ci-C6-halogenalkyl, phenyl-Chb, halogenphenyl-Chb, phenyl, halogenphenyl and three-, four-, five- or six-membered carbo- and heterocycle, wherein the carbo- and heterocycle is unsubstituted or is substituted with substituents R8b as defined below.
According to still another embodiment of formula I, R8 is selected from Ci-C6-alkyl, Ci-C6-halo- genalkyl or Ci-C6-alkyl which is substituted, Ci-C6-halogenalkyl, phenyl, halogenphenyl and three-, four-, five- or six-membered carbo- and heterocycle, wherein the carbo- and heterocycle is unsubstituted or substituted withsubstituents R8b as defined below. According to one embodi- ment thereof, the carbo- and heterocycle is unsubstituted. In a particular embodiment, R8 is selected from substituted Ci-C6-halogenalkyl, phenyl, halogenphenyl and three-, four-, five- or six- membered carbo- and heterocycle, wherein the carbo- and heterocycle is unsubstituted or substituted withsubstituents R8b as defined below.
According to another embodiment of formula I, R8 is selected from Ci-C6-alkyl, Ci-C6-halogen- alkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloal- kyl, C3-C6-halogencycloalkyl, Ci-C6-alkylaryl, six-membered heteroaryl or aryl which is unsubstituted or substituted with halogen or Ci-C6-halogenalkyl, and wherein the acyclic moieties of R8 are unsubstituted or substituted with identical or different groups R8a as defined below and wherein wherein the carbocycle, heterocycle and heteroaryl and aryl moieties are unsubstituted or substituted with substituents R8b as defined below.
According to still another embodiment of formula I, R8 is selected from Ci-C6-alkyl, Ci-C6-halo- genalkyl, CN, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, C3-C6- cycloalkyl, C3-C6-halogencycloalkyl, Ci-C6-alkylaryl, phenyl, pyridine, pyrimidine, thiophene, imidazole, triazol, oxadiazol wherein the acyclic moieties of R8 are unsubstituted or substituted with identical or different groups R8a as defined below and wherein wherein the carbocycle, heterocycle and heteroaryl and aryl moieties are unsubstituted or substituted with substituents R8b as defined below.
According to still another embodiment of formula I, R8 is Ci-C6-alkyl such as CH3, C2H5, n-pro- pyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
According to still another embodiment of formula I, R8 is Ci-C6-alkyl such as CH3.
According to still another embodiment of formula I, R8 is Ci-C6-alkyl such as C2H5.
According to still another embodiment of formula I, R8 is Ci-C6-alkyl such as CH3, C2H5, n-pro- pyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl which is substituted with at least one group R8a, which independently of one another are selected from:
R8a halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkoxy, Ci-C4-halogenalkoxy, d-Ce-alkylthio, Ci-C6- halogenalkylthio, S(0)n-Ci-C6-alkyl, S(0)n-aryl, CH(=0), C(=0)Ci-C6-alkyl, C(=0)0(Ci-C6-alkyl), C(=0)NH(Ci-C6-alkyl), C(=0)N(Ci-C6-alkyl)2, CR'=NOR" a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, five-, six- or ten-membered heteroaryl, aryl or phenoxy, wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(=0) and C(=S), and wherein the heterocycle and heteroaryl contains independently one, two, three or four heteroatoms selected from N, O and S; wherein the carbocyclic, heterocyclic, heteroaryl, aryl and phenyl groups are independently unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH, CN, NO2, SH, NH2, NH(Ci-C4- alkyl), N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkylthio, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy, and S(0)n-Ci-C6-alkyl.
According to still another embodiment of formula I, R8 is CH3 is substituted with at least one group R8a, which independently of one another are selected from:
R8a halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkoxy, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, Ci-C6- halogenalkylthio, S(0)n-Ci-C6-alkyl, S(0)n-aryl, CH(=0), C(=0)Ci-C6-alkyl, C(=0)0(Ci-C6-alkyl), C(=0)NH(Ci-C6-alkyl), C(=0)N(Ci-C6-alkyl)2, CR'=NOR", a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, five-, six- or ten-membered heteroaryl, an aryl or phenoxy, wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(=0) and C(=S), and wherein the heterocycle and heteroaryl contains independently one, two, three or four heteroatoms selected from N, O and S; wherein the carbocyclic, heterocyclic, heteroaryl, heteroaryl and phenyl groups are independently unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, Ci- C6-alkylthio, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy, and S(0)n-Ci- Ce-alkyl.
According to still another embodiment of formula I, R8 is C2H5 is substituted with at least one group R8a, which independently of one another are selected from:
R8a halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, d-C6-alkoxy, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, Ci-C6- halogenalkylthio, S(0)n-Ci-C6-alkyl, S(0)n-aryl, CH(=0), C(=0)Ci-C6-alkyl, C(=0)0(Ci-C6-alkyl), C(=0)NH(Ci-C6-alkyl), C(=0)N(Ci-C6-alkyl)2, CR'=NOR"a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, five-, six- or ten-membered heteroaryl, phenyl or phenoxy; wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(=0) and C(=S), and wherein the heterocycle and heteroaryl contains independently one, two, three or four heteroatoms selected from N, O and S; wherein the carbocyclic, heterocyclic, heteroaryl, aryl and phenyl groups are independently unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH, CN, N02, SH, NH2, NH(Ci- C4-alkyl), N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-al- kylthio, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy, and S(0)n-Ci-C6- alkyl.
According to still another embodiment of formula I, R8 is CH2CN.
According to still another embodiment of formula I, R8 is CH2OH.
According to still another embodiment of formula I, R8 is Ci-C6-halogenalkyl, in particular Ci-C4- halogenalkyl, more specifically Ci-C2-halogenalkyl, such as CF3, CCI3, FCH2, CICH2, F2CH, CI2CH, CF3CH2, CCI3CH2 or CF2CHF2.
According to still another embodiment of formula I, R8 is CH2F.
According to still another embodiment of formula I, R8 is CHF2.
According to still another embodiment of formula I, R8 is CF3.
According to still a further embodiment of formula I, R8 is C2-C6-alkenyl, in particular C2-C4-alk- enyl, such as CH=CH2, CH2CH=CH2 or C(CH3)C=CH2.
According to a further specific embodiment of formula I, R8 is C2-C6-halogenalkenyl, in particular C2-C4-halogenalkenyl, more specifically C2-C3-halogenalkenyl such as CH=CHF, CH=CHCI, CH=CF2, CH=CCI2, CF=CF2, CCI=CCI2, CH2CH=CHF, CH2CH=CHCI, CH2CH=CF2,
CH2CH=CCI2, CH2CF=CF2, CH2CCI=CCI2, CF2CF=CF2 or CCI2CCI=CCI2.
According to still a further embodiment of formula I, R8 is C2-C6-cycloalkenyl, in particular C2-C4- cycloalkenyl, such as CH=CH2-cPr.
According to still a further embodiment of formula I, R8 is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as C CH, C=C-CI,
CH2- C≡CH, CH2-C≡CCI or CH2- C≡C-CH3.
According to still a further embodiment of formula I, R8 is C2-C6-cycloalkynyl in particular C2-C4- cycloalkynyl, such as C C-cPr.
According to a further specific embodiment of formula I, R8 is Ci-C6-alkoxy, in particular C1-C4- alkoxy, more specifically Ci-C2-alkoxy such as OCH3, CH2CH3 or CH2OCH3.
According to a further specific embodiment of formula I, R8 is Ci-C6-alkyl-Ci-C6-alkoxy, in particular Ci-C4-alkyl-Ci-C4-alkoxy, more specifically Ci-C2-alkyl-Ci-C2-alkoxy, such as
According to a further specific embodiment of formula I, R8 is C2-C6-alkenyloxy, in particular C2- C4-alkenyloxy, more specifically Ci-C2-alkenyloxy such as OCH=CH2, OCH2CH=CH2
OC(CH3)CH=CH2, CH2OCH=CH2, or CH2OCH2CH=CH2.
According to a further specific embodiment of formula I, R8 is C2-C6-alkynyloxy, in particular C2- C4-alkynyloxy, more specifically Ci-C2-alkynyloxy such as OC CH, OChbC CH or ChbOC CH
According to a further specific embodiment of formula I, R8 is Ci-C6-halogenalkoxy, in particular Ci-C4-halogenalkoxy, more specifically Ci-C2-halogenalkoxy such as OCF3, OCHF2, OCH2F, OCCI3, OCHC or OCH2CI, in particular OCF3, OCHF2, OCCI3 or OCHCI2.
According to a further specific embodiment of formula I, R8 is Ci-C6-alkyl-Ci-C6-halogenalkoxy, in particular Ci-C4-alkyl-Ci-C4-halogenalkoxy, more specifically Ci-C2-alkyl-Ci-C2-halogenalkoxy such as CH2OCF3, CH2OCHF2, CH2OCH2F, CH2OCCI3, CH2OCHCI2 or CH2OCH2CI, in particular CH2OCF3, CH2OCHF2, CH2OCCI3 or CH2OCHCI2.
According to a further specific embodiment of formula I, R8 is CH(=0), C(=0)Ci-C6-alkyl, C(=0)0(Ci-C6-alkyl), C(=0)NH(Ci-C6-alkyl) or C(=0)N(Ci-C6-alkyl)2, wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
According to a further specific embodiment of formula I, R8 is Ci-C4-alkyl-CH(=0), Ci-C4-alkyl- C(=0)Ci-C6-alkyl, Ci-C4-alkyl-C(=0)0(Ci-C6-alkyl), Ci-C4-alkyl-C(=0)NH(Ci-C6-alkyl) or Ci-C4- alkyl-C(=0)N(Ci-C6-alkyl)2, especially CH2CH(=0), CH2C(=0)Ci-C6-alkyl, CH2C(=0)0(Ci-C6- alkyl), CH2C(=0)NH(Ci-C6-alkyl) or CH2C(=0)N(Ci-C6-alkyl)2 wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
According to a further specific embodiment of formula I, R8 is CR'=NOR" such as
C(CH3)=NOCH3, C(CH3)=NOCH2CH3 or C(CH3)=NOCF3.
According to a further specific embodiment of formula I, R8 is Ci-C6-alkyl-NH(Ci-C4-alkyl) orCi- C6-alkyl-N(Ci-C4-alkyl)2, wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.
According to a further specific embodiment of formula I, R8 is Ci-C6-alkylthio, in particular C1-C4- alkoxy, more specifically Ci-C3-alkylthio such as CH2SCH3 or CH2SCH2CH3.
According to a further specific embodiment of formula I, R8 is Ci-C6-alkyl-S(0)n-Ci-C6-alkyl, wherein alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl and n is 1 , 2 or 3.
According to a further specific embodiment of formula I, R8 is Ci-C6-alkyl-S(0)n-Ci-C6- halogenalkyl, wherein halogenalkyl is CF3 or CHF2 and n is 1 , 2 or 3.
According to a further specific embodiment of formula I, R8 is Ci-C6-alkyl-S(0)n-aryl, wherein the aryl or phenyl moiety in each case is unsubstituted or substituted with identical or different groups R8b which independently of one another are selected from halogen, Ci-C2-alkyl, C1-C2- alkoxy, Ci-C2-halogenalkyl, Ci-C2-halogenalkoxy and S(0)n-Ci-C6-alkyl, in particular F, CI, Br, CH3, OCH3, CF3, CHF2, OCHF2, OCF3. According to one embodiment, R8 is unsubstituted phenyl. According to another embodiment, R8 is phenyl, that is substituted with one, two or three, in particular one, halogen, in particular selected from F, CI and Br, more specifically selected from F and CI.
According to a further specific embodiment of formula I, R8 is Ci-C6-alkyl-NH-S02-Rx wherein Rx is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted with one, two, three, four or five substituents Rx2 independently selected from Ci-C4-alkyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy, or Ci-C4-halogenalkoxy, such as ChbNHSC^CFs or
According to still another embodiment of formula I, R8 is selected from Ci-C6-alkyl which is sub- stituted, a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle, in particular three-, four-, five- or six-membered, wherein the carbocycle is unsubstituted or substituted with substituents R8b as defined below. According to one embodiment thereof, the carbocycle is unsubstituted.
According to one embodiment, R8 is selected from Ci-C6-alkyl, especially CH2 which is substi- tuted with a 3-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b.
According to one embodiment, R8 is selected from Ci-C6-alkyl, especially CH2 which is substituted with a 4-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b.
According to one embodiment, R8 is selected from Ci-C6-alkyl, especially CH2 which is substituted with a 5-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b.
According to one embodiment, R8 is selected from Ci-C6-alkyl, especially Chb which is substituted with a 6-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b.
According to a further specific embodiment of formula I, R8 is Ci-C6-alkylheterocycle, especially CH2 substituted with a 4-membered saturated heterocyde which contains 1 or 2 heteroatoms, in particular 1 heteroatom, from the group consisting of N, O and S, as ring members. According to one embodiment, the heterocyde contains one O as heteroatom. For example, the formed heterocyde is oxetane. According to one embodiment thereof, the heterocyde is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b.
According to a further specific embodiment of formula I, R8 is Ci-C6-alkylheterocycle, especially CH2 substituted with a 5-membered saturated heterocyde which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S, as ring members. According to one embodiment, the heterocyde contains one O as heteroatom. According to one embodiment thereof, the heterocyde is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b.
According to a further specific embodiment of formula I, R8 is Ci-C6-alkylheterocycle, especially CH2 subsitited by a 6-membered saturated heterocyde which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S as ring members. According to one embodiment thereof, the heterocyde is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b. According to one specific embodiment thereof, said 6-membered saturated heterocyde contains 1 or 2, in particular 1 , heteroatom(s) O. According to one embodiment thereof, the respective 6-membered heterocyde is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b.
According to a further specific embodiment of formula I, R8 is Ci-C6-alkylheterocycle, especially CH2 substituted with a 5-membered saturated heterocyde which contains one N as ring member and optionally one or two groups CH2 are replaced by C(=0).
According to still another embodiment of formula I, R8 is a partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle, in particular three-, four-, five- or six-membered, wherein the carbocycle is unsubstituted or substituted with substituents R8b as defined below. According to one embodiment thereof, the carbocycle is unsubstituted.
According to still another embodiment of formula I, R8 is a partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocyde, in particular three-, four-, five- or six-membered, wherein the heterocyde contains one, two, three or four heteroatoms selected from N, O and S, and wherein the carbocycle and heterocyde are unsubstituted or substituted with substituents R8b as defined below. According to one embodiment thereof, the carbocycle or heterocyde is unsubstituted.
According to still a further embodiment, R8 is a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocyde, in particular three-, four-, five- or six-membered, wherein the heterocyde contains one, two, three or four heteroatoms selected from N, O
and S, and wherein the carbocycle and heterocycle are unsubstituted or substituted with substit- uents R8b as defined below. According to one embodiment thereof, the carbocycle or heterocycle is unsubstituted.
According to still another embodiment of formula I, R8 is a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle, in particular three-, four-, five- or six-mem- bered, wherein the carbocycle is unsubstituted or substituted with substituents R8b as defined below. According to one embodiment thereof, the carbocycle is unsubstituted.
According to one embodiment, R8 is a 3-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b.
According to one embodiment, R8 is a 3-membered saturated carbocycle, which is
unsubstituted such as cyclopropyl.
According to one embodiment, R8 is a 3-membered saturated carbocycle, which is substituted with halogen, more specifically by F, such as C3H3F2.
According to one embodiment, R8 is a 3-membered saturated carbocycle, which is substituted with halogen. More specifically by CI, such as C3H3CI2.
According to one embodiment, R8 is a 4-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b.
According to one embodiment, R8 is a 5-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b.
According to one embodiment, R8 is a 6-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b.
According to still another embodiment of formula I, R8 is a partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered heterocycle, in particular three-, four-, five- or six-membered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the heterocycle is unsubstituted or substituted with substituents R8b as defined below. According to one embodiment thereof, the heterocycle is unsubstituted.
According to still another embodiment of formula I, R8 is a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered heterocycle, in particular three-, four-, five- or six-membered, wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, and wherein the heterocycle is unsubstituted or substituted with substituents R8b as de- fined below. According to one embodiment thereof, the heterocycle is unsubstituted.
According to still another embodiment of formula I, in the embodiments of R8 described above, the heterocycle contains preferably one, two or three, more specifically one or two heteroatoms selected from N, O and S. More specifically, the hetereocycle contains one heteroatom selected from N, O and S. In particular, the heterocycle contains one or two, in particular one O.
According to one embodiment, R8 is a 4-membered saturated heterocycle which contains 1 or 2 heteroatoms, in particular 1 heteroatom, from the group consisting of N, O and S, as ring members. According to one embodiment, the heterocycle contains one O as heteroatom. For example, the formed heterocycle is oxetane. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b.
According to still another embodiment of formula I, R8 is a 5-membered saturated heterocycle which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S, as ring members. According to one embodiment, the heterocycle contains one O as heteroa- torn. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b.
According to still another embodiment of formula I, R8 is a 6-membered saturated heterocycle which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S as ring members. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b. According to one specific embodiment thereof, said 6-membered saturated heterocycle contains 1 or 2, in particular 1 , heteroatom(s) O. According to one embodiment thereof, the respective 6-membered heterocycle is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b.
According to still another embodiment of formula I, R8 is phenyl-Ci-C6-alkyl, such as phenyl- CH2, wherein the phenyl moiety in each case is unsubstituted or substituted with one, two or three identical or different groups R8b which independently of one another are selected from CN, halogen, Ci-C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, Ci-C2-halogenalkoxy and S(0)n-Ci-C6- alkyl, in particular from CN, F, CI, Br, CH3, OCH3, CF3, CHF2, OCHF2, OCF3 and S(0)2CH3.
According to still another embodiment of formula I, R8 is aryl, in particular phenyl, wherein the aryl or phenyl moiety in each case is unsubstituted or substituted with identical or different groups R8b which independently of one another are selected from CN, halogen, Ci-C2-alkyl, Ci- C2-alkoxy, Ci-C2-halogenalkyl, Ci-C2-halogenalkoxy and S(0)n-Ci-C6-alkyl, in particular from CN, F, CI, Br, CH3, OCH3, CF3, CHF2, OCHF2, OCF3. According to one embodiment, R8 is unsubstituted phenyl. According to another embodiment, R8 is phenyl, that is substituted with one, two or three, in particular one, halogen, in particular selected from F, CI and Br, more specifically selected from F and CI.
According to still another embodiment of formula I, R8 is a 5-membered heteroaryl such as pyr- rol-1 -yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1 -yl, pyrazol- 3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1 -yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2- yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1 ,2,4-triazolyl-1 -yl, 1 ,2,4-triazol-3-yl 1 ,2,4-triazol-5-yl, 1 ,2,4-oxadiazol-3-yl, 1 ,2,4-oxadiazol-5-yl and 1 ,2,4-thiadiazol-3-yl, 1 ,2,4-thia- diazol-5-yl.
According to still another embodiment of formula I, R8 is a 6-membered heteroaryl, such as pyri-
din-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, py- rimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl.
According to a further specific embodiment of formula I, R8 is Ci-C6-alkyl, especially Chb subsitited by a 5-membered saturated heteroaryl which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b.
According to a further specific embodiment of formula I, R8 is Ci-C6-alkyl, especially Chb subsitited by a 5-membered saturated heteroaryl which contains one N as ring member.
According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b.
According to a further specific embodiment of formula I, R8 is Ci-C6-alkyl, especially Chb subsitited by a 5-membered saturated heteroaryl which contains two N as ring members.
According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b.
According to a further specific embodiment of formula I, R8 is Ci-C6-alkyl, especially Chb subsitited by a 5-membered saturated heteroaryl which contains three N as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b. According to one specific embodiment thereof, said 5-membered saturated heterocycle contains 1 or 2, in particular 1 , heteroatom(s) O.
According to a further specific embodiment of formula I, R8 is Ci-C6-alkyl, especially Chb subsitited by a 5-membered saturated heteroaryl which contains one S as ring member.
According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b.
According to a further specific embodiment of formula I, R8 is Ci-C6-alkyl, especially Chb subsitited by a 5-membered saturated heteroaryl which contains one S and one N as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b. According to a further specific embodiment of formula I, R8 is Ci-C6-alkyl, especially Chb subsitited by a 5-membered saturated heteroaryl which contains one S and two N as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b.
According to a further specific embodiment of formula I, R8 is Ci-C6-alkyl, especially Chb subsitited by a 5-membered saturated heteroaryl which contains one oxygen and one N as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8 .
According to a further specific embodiment of formula I, R8 is Ci-C6-alkyl, especially Chb subsitited by a 5-membered saturated heteroaryl which contains one oxygen and two N as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not
carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b.
According to a further specific embodiment of formula I, R8 is Ci-C6-alkyl, especially Chb subsitited by a 6-membered saturated heteroaryl which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b.
According to a further specific embodiment of formula I, R8 is Ci-C6-alkyl, especially Chb subsitited by a 6-membered saturated heteroaryl which one N as ring member. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b.
According to a further specific embodiment of formula I, R8 is Ci-C6-alkyl, especially Chb subsitited by a 6-membered saturated heteroaryl which two N as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b.
According to a further specific embodiment of formula I, R8 is Ci-C6-alkyl, especially Chb subsitited by a 10-membered saturated heteroaryl which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of N, O and S as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b. According to one specific embodiment thereof, said 10-membered saturated heterocycle contains 1 or 2, in particular 1 , heteroatom(s) N.
According to a further specific embodiment of formula I, R8 is Ci-C6-alkyl, especially Chb subsitited by a 10-membered saturated heteroaryl which one N as ring members. According to one embodiment thereof, the heteroaryl is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b.
According to still another embodiment of formula I, R8 is Chb substituted with a 5-membered heteroaryl such as pyrrol-1 -yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1 -yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1 -yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1 ,2,4-triazolyl-
1 - yl, 1 ,2,4-triazol-3-yl 1 ,2,4-triazol-5-yl, 1 ,2,4-oxadiazol-3-yl, 1 ,2,4-oxadiazol-5-yl and 1 ,2,4- thiadiazol-3-yl, 1 ,2,4-thiadiazol-5-yl.
According to still another embodiment of formula I, R8 is Chb substituted with a 6-membered heteroaryl, such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-
2- yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl and 1 ,3,5-triazin-2-yl and 1 ,2,4-triazin-3-yl.
According to a further particular embodiment, R8 is selected from Ci-C6-alkyl, Ci-C6-halogen- alkyl, CN, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, aryl, heteroaryl, three-, four-, five- or six-membered carbocycle and heterocycle, phenoxy, and C1-C6- alkyl substituted with CN, three-, four-, five- or six-membered carbocycle and heterocycle, aryl and heteroaryl; wherein the carbocycle and heterocycle is unsubstituted or carries one, two,
three or four substituents R8b as defined below. According to one embodiment thereof, the car- bocycle, heterocycle, heteroaryl and aryl are unsubstituted. In a particular embodiment, R8 is selected from Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-al- kynyl, C2-C6-halogenalkynyl, aryl, heteroaryl, cypropropyl and Ci-C6-alkyl substituted with aryl and heteroaryl; wherein the aryl and heteroaryl are unsubstituted or carries one, two, three or four substituents R8b as defined below.Particularly preferred embodiments of R8 according to the invention are in Table P8 below, wherein each line of lines P8-1 to P8-182 corresponds to one particular embodiment of the invention, wherein P8-1 to P8-182 are also in any combination with one another a preferred embodiment of the present invention. The connection point to the carbon atom, to which R8 is bound is marked with "#" in the drawings.
According to still another embodiment of formula I, R7, R8 together with the carbon atom to which they are bound form a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- or heterocycle; wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, wherein the heteroatom N may carry one substituent RN selected from Ci-C4-alkyl, Ci-C4-halogenalkyl and S02Ph, wherein Ph is un- substituted phenyl or phenyl that is substituted with one, two or three substituents selected from CN, Ci-C4-alkyl, halogen, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy; and wherein the heteroatom S may be in the form of its oxide SO or SO2, and wherein the carbocy- cle or heterocycle is unsubstituted or carries one, two, three or four substituents R78 independently selected from halogen, OH, CN, NO2, SH, NH2, d-Ce-alkyl, d-Ce-halogenalkyl, Ci- C6-alkoxy, Ci-C6-halogenalkoxy, Ci-C6-alkylthio, Ci-C6-halogenalkylthio, Ci-C4-alkoxy-Ci-C4- alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or carry one, two, three, four or five substituents R78a selected from the group consisting of CN, halogen, OH, Ci-
C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy; and wherein in each case one or two CH2 groups of the carbo- or heterocycle may be replaced by a group independently selected from C(=0) and C(=S).
According to one embodiment, R7 and R8 form a 3-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b.
According to one embodiment, R7 and R8 form a 4-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b.
According to one embodiment, R7 and R8 form a 5-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b.
According to one embodiment, R7 and R8 form a 6-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b.
According to one embodiment, R7 and R8 form a 7-membered saturated carbocycle. According to one embodiment thereof, the carbocycle is unsubstituted, i.e. it does not carry any substituent R8b. According to still another embodiment of formula I, it is substituted with R8b.
According to one embodiment, R7 and R8 together with the carbon atom to which they are bound form a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered heterocycle that is unsubstituted or substituted. According to a further embodiment, the heterocycle formed by R7 and R8 is saturated.
According to a further embodiment, the heterocycle formed by R7 and R8 is a saturated unsubstituted or substituted heterocycle, wherein the heterocycle contains one, two or three, more particularly one or two, specifically one, heteroatom(s) selected from NH, NRN, O, S, S(=0) and S(=0)2, wherein RN is defined and preferably defined above. According to one embodiment, this saturated heterocycle is unsubstituted. According to a further embodiment, the saturated heterocycle carries one, two, three or four substituents R78. In one further particular embodiment, said heterocycle is four- or six-membered.
According to a further embodiment, the unsubstituted or substituted and saturated or partially unsaturated heterocycle is three-, four-, five- or six-membered and contains one, two or three, more particularly one or two, heteroatoms selected from NH, NRN, O, S, S(=0) and S(=0)2, wherein RN is as defined above or preferably selected from Ci-C2-alkyl, Ci-C2-halogenalkyl and S02Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted with one Ci-C2-alkyl. In one further particular embodiment, said heterocycle is four- or six-membered.
According to a further embodiment, the heterocycle formed by R7 and R8 contains one, two or three, more specifically one or two, heteroatoms selected from NH and NRN, wherein RN is as defined and preferably defined below, more particularly selected from Ci-C2-alkyl, Ci-C2-halo- genalkyl and S02Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted with one methyl. In one embodiment thereof, it contains one or two heteroatoms NH, in particular one NH. In another embodiment, it contains one or two heteroatoms NRN, in particular one NRN,
wherein RN in each case is as defined and preferably defined above.
According to a further embodiment, the heterocycle formed by R7 and R8 contains one, two or three, more specifically one or two, in particular one, heteroatom(s) selected from S, S(=0) and S(=0)2. In one embodiment thereof, it contains one or two heteroatoms S, in particular one S. In another embodiment, it contains one or two heteroatoms S(=0), in particular one S(=0). In still another embodiment, it contains one or two heteroatoms S(=0)2, in particular one S(=0)2.
According to a further embodiment, the heterocycle formed by R7 and R8 contains one or two heteroatoms O. In one embodiment thereof, it contains one heteroatom O. In another embodiment, it contains two heteroatoms O.
According to a further embodiment, the heterocycle formed by R7 and R8 is unsubstituted, i.e. it does not carry any substituent R78. According to a further embodiment, it carries one, two, three or four R78.
According to one particular embodiment, R7 and R8 together form a 4-membered saturated heterocycle which contains 1 or 2 heteroatoms, in particular 1 heteroatom, from the group consist- ing of NH, NRN, O, S, S(=0) and S(=0)2, as ring members, wherein RN is defined and preferably defined above. In one embodiment, the heterocycle contains one O as heteroatom. For example, the formed heterocycle is oxetane. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R78. According to a further embodiment, it carries one, two, three or four R78.
According to a further particular embodiment, R7 and R8 together form a 5-membered saturated heterocycle which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of NH, NRN, O, S, S(=0) and S(=0)2, as ring members, wherein RN is as defined and preferably defined above. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R78. According to a further embodiment, it carries one, two, three or four R78.
According to a further particular embodiment, R7 and R8 together form a 6-membered saturated heterocycle which contains 1 , 2 or 3, in particular 1 or 2, heteroatoms from the group consisting of NH, NRN, O, S, S(=0) and S(=0)2, as ring members, wherein RN is as defined and preferably defined below. According to one embodiment thereof, the heterocycle is unsubstituted, i.e. it does not carry any substituent R78. According to a further embodiment, it carries one, two, three or four R78. According to one specific embodiment thereof, said 6-membered saturated heterocycle contains 1 or 2 heteroatoms selected from NH and NRN. According to a further specific embodiment thereof, said 6-membered saturated heterocycle contains 1 or 2 heteroatoms O. According to a further specific embodiment thereof, said 6-membered saturated heterocycle contains 1 or 2 heteroatoms selected from S, S(=0) and S(=0)2. According to one embodiment thereof, the respective 6-membered heterocycle is unsubstituted, i.e. it does not carry any substituent R78. According to a further embodiment, it carries one, two, three or four R78.
According to one further embodiment R7 together with R8 and with the carbon atom to which they are bound form a saturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle, in particular three-, four-, five- or six-membered carbocycle, more specifically five- or six-membered carbocycle, that is unsubstituted or carries one, two, three or four substituents R78 as defined below. According to one embodiment thereof, R7 and R8 form a cyclopropyl, that
is unsubstituted or carries one, two, three or four substituents R78 as defined below. According to a further embodiment thereof, R7 and R8 form a cyclobutyl, that is unsubstituted or carries one, two, three or four substituents R78 as defined below. According to still a further embodiment thereof, R7 and R8 form a cyclopentyl, that is unsubstituted or carries one, two, three or four substituents R78 as defined below. According to still a further embodiment thereof, R7 and R8 form a cyclohexyl, that is unsubstituted or carries one, two, three or four substituents R78 as defined below. According to still a further embodiment thereof, R7 and R8 form a cycloheptyl, that is unsubstituted or carries one, two, three or four substituents R78 as defined below.
R78 are the possible substituents for the carbo- or heterocycle formed by R7 and R8 and are in- dependently selected from halogen, OH, CN, NO2, SH, NH2, d-Ce-alkyl, d-Ce-halogenalkyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, Ci-C6-alkylthio, Ci-C6-halogenalkylthio, Ci-C4-alkoxy-Ci-C4- alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or carry one, two, three, four or five substituents R78a selected from the group consisting of halogen, OH, C1-C4- alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy; and wherein in each case one or two CH2 groups of the carbo- or heterocycle may be replaced by a group independently selected from C(=0) and C(=S).
In one preferred embodiment, R78 is in each case independently selected from halogen, OH, CN, SH, Ci-C6-alkyl, Ci-C6-halogenalkyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy and Ci-C6-al- kylthio. In one further preferred embodiment, R78 is in each case independently selected from halogen, Ci-C6-alkyl and Ci-C6-halogenalkyl. In one further particular embodiment, R78 is in each case independently selected from Ci-C6-alkyl, such as methyl and ethyl.
RN is the substituent of the heteroatom NRN that is contained in the heterocycle formed by R7 and R8 in some of the inventive compounds. RN is selected from Ci-C4-alkyl, Ci-C4-halogenalk and S02Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted with one, two or three substituents selected from Ci-C4-alkyl. In one preferred embodiment, RN is in each case independently selected from Ci-C2-alkyl, Ci-C2-halogenalkyl and S02Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted with one methyl substituents. In one particular embodiment, RN is in each case independently selected from Ci-C2-alkyl, more particularly methyl. In one particular embodiment, RN is in each case independently selected from S02Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted with one methyl.
According to still another embodiment of formula I, R7, R8 together with the carbon atom to which they are bound form a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- or heterocycle; wherein the carbocycle or heterocycle is unsubstituted or carries one, two, three or four substituents R78 independently selected from hal- ogen, OH , CN, N02, SH, NH2, Ci-C6-alkyl, Ci-C6-halogenalkyl, Ci-C6-alkoxy, Ci-C6-halogen- alkoxy, Ci-C6-alkylthio, Ci-C6-halogenalkylthio, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or carry one, two, three, four or five substituents R78a selected from the group consisting of CN, halogen, OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy.
According to still another embodiment of formula I, R7, R8 together with the carbon atom to which they are bound form a saturated or partially unsaturated four-, five-, six-membered carbo- or heterocycle; wherein the carbocycle or heterocycle is unsubstituted or carries one, two, three
or four substituents R78 independently selected from halogen, Ci-C6-alkyl, Ci-C6-halogenalkyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy.
Particularly preferred embodiments of combinations of R7 and R8 according to the invention are in Table P78 below, wherein each line of lines P78-1 to P78-204 corresponds to one particular embodiment of the invention, wherein P8-1 to P78-204 are also in any combination with one another a preferred embodiment of the present invention. The carbon atom, to which R7 and R8 are bound is marked with * in the drawings.
Table P78
halogenalkyl, unsubstituted aryl and aryl that is substituted with one, two, three, four or five substituents Rx1 independently selected from Ci-C4-alkyl. In particular, Rx is in each case independently selected from Ci-C4-alkyl and phenyl that is substituted with one, two or three Rx1 independently selected from Ci-C2-alkyl, more specifically Rx is in each case independently
selected from Ci-C4-alkyl and phenyl that is substituted with one CH3., more specifically S02-R: is the tosyl group ("Ts").
R7a are the possible substituents for the the acyclic moieties of R7 and the R7a are in each case independently selected from halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6- halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, Ci-C6-halogenalkylthio, S(0)n-Ci-C6- alkyl, S(0)n-Ci-C6-halogenalkyl, S(0)n-aryl, CH(=0), C(=0)Ci-C6-alkyl, C(=0)OCi-C6-alkyl, C(=0)NHCi-C6-alkyl, C(=0)N(Ci-C6-alkyl)2, CR'=NOR", a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, five-, six- or ten-membered heteroaryl, aryl and phenoxy; wherein in each case one or two CH2 groups of the carbocycle and heterocycle may be replaced by a group independently selected from C(=0) and C(=S); wherein the heterocycle and heteroaryl contain independently one, two, three or four heteroatoms selected from N, O and S; wherein the carbocyclic, heterocyclic, phenyl and heteroaryl groups are independently unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH, CN, N02, SH, NH2, NH(Ci-C4- alkyl), N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkylthio, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy and S(0)n-Ci-C6-alkyl; wherein n is 0, 1 and 2;
In one preferred embodiment, R7a is in each case independently selected from halogen, OH, CN, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, heteroaryl, phenyl and halogenphenyl, wherein the halogenphenyl is substituted with halogen selected from the group consisting of F, CI and Br. In one further preferred embodiment, R7a is in each case independently selected from halogen, heteroaryl, phenyl and halogenphenyl, wherein the halogenphenyl is substituted with halogen selected from the group consisting of F, CI and Br, in particular selected from F and CI.
In one further preferred embodiment, R7a is in each case independently selected from halogen, CN, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, phenyl, and heteroaryl; wherein the heteroaryl and phenyl is substituted with halogen selected from the group consisting of F, CI and Br or by Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and C1-C4- halogenalkoxy. In one further preferred embodiment, R7a is in each case independently selected from halogen heteroaryl and phenyl wherein the heteroaryl and phenyl is substituted with halogen selected from the group consisting of F, CI and Br, in particular selected from F and CI. R7b are the possible substituents for the carbocycle, heterocycle, heteroaryl and aryl moieties are independently selected from halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-al- kyl)2, NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, Ci-C4-alkyl, Ci-C4-alkoxy, C1-C4- halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, Ci-C6-halogenalkylthio, S(0)n-Ci-C6-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or substituted with substituents selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy and Ci-C4-halogen- alkoxy.
In one preferred embodiment, R7b is in each case independently selected from halogen, OH, CN, SH, Ci-C6-alkyl, Ci-C6-halogenalkyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy and Ci-C6-al- kylthio. In one further preferred embodiment, R7b is in each case independently selected from halogen, Ci-C6-alkoxy, Ci-C6-halogenalkoxy and Ci-C6-halogenalkyl. In one further particular
embodiment, R7b is in each case independently selected from Ci-C6-alkyl, such as methyl and ethyl. In one further particular embodiment, R7b is in each case independently selected from halogen, such as F, CI and Br.
R8a are the possible substituents for the the acyclic moieties of R8 and the R8a are in each case independently selected from halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6- halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, Ci-C6-halogenalkylthio, S(0)n-C-i-C6- alkyl, S(0)n-aryl, CH(=0), C(=0)Ci-C6-alkyl, C(=0)0(Ci-C6-alkyl), C(=0)NH(Ci-C6-alkyl), CR'=NOR", a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle, five-, six- or ten-membered heteroaryl, aryl, phenoxy; wherein in each case one or two CH2 groups of the carbocycle and heterocycle may be replaced by a group independently selected from C(=0) and C(=S); wherein the heterocycle and heteroaryl contain independently one, two, three or four heteroatoms selected from N, O and S; wherein the carbocyclic, heterocyclic, phenyl and heteroaryl groups are independently unsubsti- tuted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4-alkyl),
N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, d-Ce-alkylthio, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4- alkoxy, Ci-C4-halogenalkoxy and S(0)n-Ci-C6-alkyl; wherein n is 0, 1 and 2;
According to one preferred embodiment, R8a is in each case independently selected from halo- gen, OH, CN, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, CH(=0), C(=0)Ci-C6-alkyl,
C(=0)0(Ci-C6-alkyl), C(=0)NH(Ci-C6-alkyl) and CR'=NOR".
According to one preferred embodiment, R8a is in each case independently selected from OH, CN, CH(=0), C(=0)Ci-C6-alkyl, C(=0)0(Ci-C6-alkyl), C(=0)NH(Ci-C6-alkyl) such as CN, CHO, C(0)0(CH3) ,C02NH(CH3), C02N(CH3)2 or NHS02CF3.
According to one preferred embodiment, R8a is in each case independently selected from C1-C6- alkylthio, Ci-C6-halogenalkylthio, S(0)n-Ci-C6-alkyl, S(0)n-aryl, such as SCH3, S02CH3, S02Ph.
According to one preferred embodiment, R8a is in each case independently selected from NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, such as NH(CH3), N(CH3)2 or NHS02CH3,
NHS02CF3.
According to one preferred embodiment, R8a is in each case independently selected from C3-C6- cycloalkyl, C3-C6-halogencycloalkyl, such as cyclopropyl or fully or partially halogenated cyclo- propyl.
According to one preferred embodiment, R8a is in each case independently selected from C1-C6- alkoxy, Ci-C6-halogenalkoxy, such as OCF3, OCHF2, OCH2F, OCCI3, OCHCI2 or OCH2CI, in particular OCF3, OCHF2, OCCI3 or OCHCI2.
According to one preferred embodiment, R8a is in each case independently selected from heter- ocarbocycle, wherein the heretocyclocycle is a satureated, two CH2 groups are replaced by C(=0) and contains one N as a ring member.
According to one preferred embodiment, R8a is in each case independently selected from aryl, wherein the aryl is substituted with halogen selected from the group consisting of F, CI, Br, CH3, CH F2, OCH3, OCH Fs, CN or S02CH3.
According to one prefer embodiment, R8 is unsubstituted 5- or 6-membered heteroaryl.
According to still a further embodiment, R8 is 5- or 6-membered heteroaryl substituted with halogen selected from the group consisting of F, CI, Br, CH3, CHF2, OCH3, OCHF3, CN or SO2CH3.
According to one preferred embodiment, R8a is in each case independently selected from halo- gen, OH, CN, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and heterocycle, wherein the heretocy- clocycle is a satureated and contains one N as a ring member.
According to one preferred embodiment, R8a is in each case independently selected from halogen, OH, CN, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and heterocycle, wherein the heretocy- clocycle is a satureated, one CH2 group is replaced by C(=0) and contains one N as a ring member.
According to one preferred embodiment, R8a is in each case independently selected from halogen, OH, CN, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and heterocycle, wherein the heretocy- clocycle is a satureated, two CH2 groups are replaced by C(=0) and contains one N as a ring member.
According to one preferred embodiment, R8a is in each case independently selected from halogen, OH, CN, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, phenyl, aryl, and heteroaryl, wherein the aryl and heteroaryl are substituted from the group consisting of F, CI, Br, CH3, CHF2, OCH3, OCHF3, CN or SO2CH3. According to one further preferred embodiment, R8a is in each case independently selected from halogen, phenyl, halogenphenyl and heteroaryl, wherein the
halogenphenyl is substituted with halogen selected from the group consisting of F, CI and Br, in particular selected from F and CI.
According to one further preferred embodiment, R8a is in each case independently selected from halogen, CN, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C6-alkoxy, Ci-C4-halogenalkoxy, Ci- C6-alkylthio, Ci-C6-halogenalkylthio, phenyl, wherein the phenyl is substituted with halogen se- lected from the group consisting of F, CI and Br or by Ci-C4-alkyl, Ci-C4-halogenalkyl, C1-C4- alkoxy and Ci-C4-halogenalkoxy. According to one further preferred embodiment, R8a is in each case independently selected from halogen and phenyl wherein the phenyl is substituted with halogen selected from the group consisting of F, CI and Br, in particular selected from F and CI.
R8b are the possible substituents for the carbocycle, heterocycle, heteroaryl and aryl moieties and are independently selected from halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4- alkyl)2, N H(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, Ci-C4-alkyl, Ci-C4-alkoxy, Ci- C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-al- kylthio, Ci-C6-halogenalkylthio, S(0)n-Ci-C6-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and phe- noxy, wherein the phenyl groups are unsubstituted or substituted with substituents selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci- C4-halogenalkoxy.
According to one preferred embodiment, R8b is in each case independently selected from halogen, OH, CN, SH , Ci-C6-alkyl, Ci-C6-halogenalkyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, C1-C6- alkylthio and S(0)n-Ci-C6-alkyl. According to one further preferred embodiment, R8b is in each case independently selected from halogen, Ci-C6-alkoxy, Ci-C6-halogenalkyl, Ci-C6-halogen- alkoxy and S(0)n-Ci-C6-alkyl. According to one further particular embodiment, R8b is in each
case independently selected from Ci-C6-alkyl, such as methyl and ethyl. According to one further particular embodiment, R8b is in each case independently selected from halogen, such as F, CI and Br. According to one further particular embodiment, R8b is in each case independently selected from Ci-C6-alkoxy, such as OCH3. According to one further particular embodiment, R8b is in each case independently selected from Ci-C4-halogenalkoxy, such as OCHF2 and OCF3. According to one further particular embodiment, R8b is in each case independently selected from S(0)n-Ci-C6-alkyl. such as SO2CH3.
R9 according to the invention is in each case independently selected from H OH, CN, NO2, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci- C6-alkoxy, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; and wherein
Rx is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted with one, two, three, four or five substituents Rx9 independently selected from Ci-C4-alkyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the acyclic moieties of R9 are unsubstituted or substituted with identical or different groups R9a which independently of one another are selected from:
R9a halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalky, Ci-C4-halogen- alkoxy, Ci-C6-alkylthio, aryl and phenoxy, wherein the aryl and phenoxy group is unsubstituted or unsubstituted or substituted with R9 a selected from the group consisting of halogen, OH, Ci- C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the carbocyclic, heteroaryl and aryl moieties of R9 are unsubstituted or substituted with identical or different groups R9b which independently of one another are selected from:
R9 halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6- halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio.
For every R9 that is present in the inventive compounds, the following embodiments and preferences apply independently of the meaning of any other R9 that may be present in the ring.
According to one embodiment of formula I, R9 is H or Ci-C6-alkyl, in particular H or CH3.
According to still another embodiment of formula I, R9 is OH.
According to still another embodiment of formula I, R9 is CN.
According to still another embodiment of formula I, R9 is SH.
According to still another embodiment of formula I R9 is NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2 or NH-S02-RX, wherein Rx is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted with one, two, three, four or five substituents Rx9 independently selected from Ci-C4-al- kyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy, or Ci-C4-halogenalkoxy. In particular Ci-C4-alkyl, such as NHCH3 and N(CH3)2. In particular Rx is Ci-C4-alkyl, and phenyl that is substituted with one CH3, more specifically S02-Rx is CH3 and tosyl group ("Ts").
According to still another embodiment of formula I, R9 is Ci-C6-alkyl, in particular Ci-C4-alkyl, such as CH3 or CH2CH3.
According to still another embodiment of formula I, R9 is Ci-C6-halogenalkyl, in particular C1-C4- halogenalkyl, such as CF3, CHF2, CH2F, CCI3, CHC , CH2CI, CF3CH2, CCI3CH2 or CF2CHF2.
According to still another embodiment of formula I, R9 is C2-C6-alkenyl or C2-C6-halogenalkenyl, in particular C2-C4-alkenyl or C2-C4-halogenalkenyl, such as CH=CH2, C(CH3)=CH2, CH=CCI2, CH=CF2, CCI=CCI2, CF=CF2, CH=CH2, CH2CH=CCI2, CH2CH=CF2, CH2CCI=CCI2, CH2CF=CF2, CCI2CH=CCI2, CF2CH=CF2, CCI2CCI=CCI2, or CF2CF=CF2.
According to still another embodiment of formula I, R9 is C2-C6-alkynyl or C2-C6-halogenalkynyl, in particular C2-C4-alkynyl or C2-C4-halogenalkynyl, such as C≡CH, C≡CCI, C≡CF. CH2C≡CH, CH2C≡CCI, or CH2C≡CF.
According to still another embodiment of formula I, R9 is Ci-C6-alkoxy, in particular C1-C4- alkoxy, more specifically Ci-C2-alkoxy such as OCH3 or OCH2CH3.
According to still another embodiment of formula I, R9 is Ci-C6-halogenalkoxy, in particular Ci- C4-halogenalkoxy, more specifically Ci-C2-halogenalkoxy such as OCF3, OCHF2, OCH2F, OCCI3, OCHC or OCH2CI, in particular OCF3, OCHF2, OCCI3 or OCHCI2.
According to still another embodiment of formula I R9 is C3-C6-cycloalkyl, in particular cyclopro- pyl.
According to still another embodiment of formula I, R9 is C3-C6-cycloalkyl, for example cyclopro- pyl, substituted with one, two, three or up to the maximum possible number of identical or different groups R9 b as defined and preferably herein.
According to still another embodiment of formula I, R9 is C3-C6-halogencycloalkyl. In a special embodiment R9 is fully or partially halogenated cyclopropyl.
According to still another embodiment of formula I, R9 is unsubstituted aryl or aryl that is substituted with one, two, three or four R9b, as defined herein. In particular, R9 is unsubstituted phenyl or phenyl that is substituted with one, two, three or four R9b, as defined herein.
According to still another embodiment of formula I, R9 is unsubstituted 5- or 6-membered heteroaryl. According to still a further embodiment, R9 is 5- or 6-membered heteroaryl that is substituted with one, two or three R9b, as defined herein.
According to still another embodiment of formula l,R9 is in each case independently selected from H, OH, CN, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, C2-C6- alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy and C3-C6-cycloalkyl; wherein the acyclic moieties of R9 are not further substituted or carry one, two, three, four or five identical or different groups R9a as defined below and wherein the carbocyclic, heteroaryl and aryl moieties of R9 are not further substituted or carry one, two, three, four or five identical or different groups R9b as defined below.
According to still another embodiment of formula I, R9 is independently selected from H OH, Ci- C6-alkyl, Ci-C6-halogenalkyl, Ci-C6-alkoxy and Ci-C6-halogenalkoxy, in particular independently selected from H, CN, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogen- alkoxy.
R9a are the possible substituents for the acyclic moieties of R9 .
R9a according to the invention is independently selected from halogen, OH, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, aryl and phe- noxy, wherein the aryl and phenoxy group is unsubstituted or unsubstituted or substituted with R9 a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, C1-C4- alkoxy and Ci-C4-halogenalkoxy, in particular selected from halogen, Ci-C2-alkyl, Ci-C2-halo- genalkyl, Ci-C2-alkoxy and Ci-C2-halogenalkoxy, more specifically selected from halogen, such as F, CI and Br.
In to one embodiment R9a is independently selected from halogen, OH, CN, Ci-C2-alkoxy, C3- C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C2-halogenalkoxy. Specifically, R9a is
independently selected from F, CI, OH, CN, Ci-C2-alkoxy, cyclopropyl, 1 -F-cyclopropyl, 1 -CI- cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1 -Cl2-cyclopropyl and Ci-C2-halogenalkoxy.
According to one embodiment R9a is independently selected from halogen, such as F, CI, Br and I, more specifically F, CI and Br.
According to still another embodiment of formula I, R9a is independently selected from OH, C3- C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C2-halogenalkoxy. Specifically, R9a is
independently selected from OH, cyclopropyl and Ci-C2-halogenalkoxy.
According to still another embodiment of formula I, R9a is independently selected from aryl and phenoxy, wherein the aryl and phenoxy group is unsubstituted or substituted with R9a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci- C4-halogenalkoxy, in particular selected from halogen, Ci-C2-alkyl, Ci-C2-halogenalkyl, C1-C2- alkoxy and Ci-C2-halogenalkoxy, more specifically selected from halogen, such as F, CI and Br.
R9b are the possible substituents for the carbocyclic, heteroaryl and aryl moieties of R9 .
R9b according to the invention is independently selected from halogen, OH, CN, Ci-C4-alkyl, Ci- C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and Ci-C4-halogen- alkoxy.
According to one embodiment thereof R9b is independently selected from halogen, CN, C1-C2- alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and C1-C2- halogenalkoxy. Specifically, R9 b is independently selected from F, CI, Br, OH, CN, CH3, OCH3, CHF2, OCHF2, cyclopropyl, 1 -F-cyclopropyl, 1 -CI-cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1 -C - cyclopropyl, OCF3, and OCHF2.
According to still another embodiment thereof R9b is independently selected from halogen, Ci- C2-alkyl, Ci-C2-alkoxy, Ci-C2-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl and C1-C2- halogenalkoxy. Specifically, R9 b is independently selected from halogen, CN, OH, CH3, CHF2, OCHF2, OCF3, OCH3, cyclopropyl, 1 -F-cyclopropyl, 1 -CI-cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1 -C - cyclopropyl and halogenmethoxy, more specifically independently selected from F, CI, OH, CH3, OCH3, CHF2, OCH3, cyclopropyl, 1 -F-cyclopropyl, 1 -CI-cyclopropyl, 1 ,1 -F2-cyclopropyl, 1 ,1 -C - cyclopropyl, OCHF2 and OCF3.
Rx in the substituent NH-S02-RX is in each case independently selected from Ci-C4-alkyl, C1-C4- halogenalkyl, unsubstituted aryl and aryl that is substituted with one, two, three, four or five substituents Rx9 independently selected from Ci-C4-alkyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy. In particular, Rx is in each case independently selected
from Ci-C4-alkyl, halogen, OH, CN and phenyl that is substituted with one, two or three Rx9 independently selected from Ci-C2-alkyl, more specifically Rx is in each case independently selected from Ci-C4-alkyl and phenyl that is substituted with one CH3, more specifically S02-R: is the tosyl group ("Ts").
Particularly preferred embodiments of R9 according to the invention are in Table P9 below, wherein each line of lines P9-1 to P9-12 corresponds to one particular embodiment of the invention. Thereby, for every R9 that is present in the inventive compounds, these specific
embodiments and preferences apply independently of the meaning of any other R9 that may be present in the ring:
Table P9:
"Ts" in the table stands for the tosylgroup S02-(p-CH3)phenyl.
The intention relates further to novel compouds of the formula I with the R1, R2, R3, R4, R5, R6, A, B, R7, R8 and R9 as defined above, with the proviso that
if R3 is ORY, RY is not C2-C6-alkyl; or
if R4 is C(=0)NH(Ci-C6-alkyl), R4a is not a substituted phenyl; or
if R5 and R6 form a phenyl, R56 is not NH2 und NH-SO2-Rx. According to one embodiment of the invention the novel compounds of the formula I having R1, R2, R4, R5, R6, A, B, R7, R8 and R9 as defined above and
R3 is in each case independently selected from halogen, OH, CN, NO2, SH, NH2, NH(Ci-C4- alkyl), N(Ci-C4-alkyl)2, NH(C2-C4-alkenyl), N(C2-C4-alkenyl)2, NH(C2-C4-alkynyl), N(C2-C4- alkynyl)2, NH(C3-C6-cycloalkyl), N(C3-C6-cycloalkyl)2, N(Ci-C4-alkyl)(C2-C4-alkenyl), N(Ci- C4-alkyl)(C2-C4-alkynyl), N(Ci-C4-alkyl)(C3-C6-cycloalkyl), N(C2-C4-alkenyl)(C2-C4-al- kynyl), N(C2-C4-alkenyl)(C3-C6-cycloalkyl), N(C2-C4-alkynyl)(C3-C6-cycloalkyl),
NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, S(0)n-Ci-C6-alkyl, S(0)n-aryl, d-Ce-cycloalkylthio, S(0)n-C2-C6-alkenyl, S(0)n-C2-C6-alkynyl, CH(=0), C(=0)Ci-C6-al- kyl, C(=0)C2-C6-alkenyl, C(=0)C2-C6-alkynyl, C(=0)C3-C6-cycloalkyl, C(=0)NH(Ci-C6- alkyl), CH(=S), C(=S)Ci-C6-alkyl, C(=S)C2-C6-alkenyl, C(=S)C2-C6-alkynyl, C(=S)C3-C6- cycloalkyl, C(=S)NH(Ci-C6-alkyl), Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-
alkynyl, ORY, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N , O and S; wherein Rx and n is as defined above;
RY is Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6- halogenalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, phenyl and phenyl-Ci- C6-alkyl; wherein the phenyl groups are unsubstituted or or carry one, two, three, four or five substituents selected from the group consisting of CN, halogen, OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the acyclic moieties of R3 are unsubstituted or substituted with groups R3a which independently of one another are selected from:
R3a halogen, OH, CN , Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4- halogenalkoxy, Ci-C6-alkylthio, aryl and phenoxy; wherein the aryl and phenoxy group is unsubstituted or substituted with substituent R31a selected from the group consisting of halogen, OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the carbocyclic, heteroaryl and aryl moieties of R3 are unsubstituted or substituted with groups R3b which independently of one another are selected from:
R3b halogen, OH, CN , Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio.
According to one further embodiment of the invention the novel compounds of the formula I having R1 , R2, R4, R5, R6, A, B, R7, R8 and R9 as defined above and
R3 is in each case independently selected from halogen, OH , CN, NO2, SH, NH2, NH(Ci-C4- alkyl), N(Ci-C4-alkyl)2, N H(C2-C4-alkenyl), N(C2-C4-alkenyl)2, N H(C2-C4-alkynyl), N(C2-C4- alkynyl)2, N H(C3-C6-cycloalkyl), N(C3-C6-cycloalkyl)2, N(Ci-C4-alkyl)(C2-C4-alkenyl), N(Ci- C4-alkyl)(C2-C4-alkynyl), N(Ci-C4-alkyl)(C3-C6-cycloalkyl), N(C2-C4-alkenyl)(C2-C4-al- kynyl), N(C2-C4-alkenyl)(C3-C6-cycloalkyl), N(C2-C4-alkynyl)(C3-C6-cycloalkyl),
NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, S(0)n-Ci-C6-alkyl, S(0)n-aryl, d-Ce-cycloalkylthio, S(0)n-C2-C6-alkenyl, S(0)n-C2-C6-alkynyl, CH(=0), C(=0)Ci-C6-al- kyl, C(=0)C2-C6-alkenyl, C(=0)C2-C6-alkynyl, C(=0)C3-C6-cycloalkyl, C(=0)N H(Ci-C6- alkyl), CH(=S), C(=S)Ci-C6-alkyl, C(=S)C2-C6-alkenyl, C(=S)C2-C6-alkynyl, C(=S)C3-C6- cycloalkyl, C(=S)N H(Ci-C6-alkyl), Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6- alkynyl, , C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; wherein Rx and n is as defined above;
wherein the acyclic moieties of R3 are unsubstituted or substituted with groups R3a which independently of one another are selected from:
R3a halogen, OH, CN , Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4- halogenalkoxy, Ci-C6-alkylthio, aryl and phenoxy; wherein the aryl and phenoxy group is unsubstituted or substituted with substituent R31a selected from the group consisting of halogen, OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the carbocyclic, heteroaryl and aryl moieties of R3 are unsubstituted or substituted with groups R3b which independently of one another are selected from:
R3b halogen, OH , CN , Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6- halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio.
According to one embodiment of the invention the novel compounds of the formula I having R1 , R2, R3, R5, R6, A, B, R7, R8 and R9 as defined above and
R4 is in each case independently selected from halogen, OH , CN , NO2, SH , N H2, N H(Ci-C4- alkyl), N(Ci-C4-alkyl)2, N H(C2-C4-alkenyl), N (C2-C4-alkenyl)2, N H(C2-C4-alkynyl), N (C2-C4- alkynyl)2, N H(C3-C6-cycloalkyl), N (C3-C6-cycloalkyl)2, N(Ci-C4-alkyl)(C2-C4-alkenyl), N (Ci- C4-alkyl)(C2-C4-alkynyl), N (Ci-C4-alkyl)(C3-C6-cycloalkyl), N (C2-C4-alkenyl)(C2-C4-al- kynyl), N(C2-C4-alkenyl)(C3-C6-cycloalkyl), N (C2-C4-alkynyl)(C3-C6-cycloalkyl),
N H(C(=0)Ci-C4-alkyl), N (C(=0)Ci-C4-alkyl)2, N H-S02-Rx, S(0)n-Ci-C6-alkyl, S(0)n-aryl, d-Ce-cycloalkylthio, S(0)n-C2-C6-alkenyl, S(0)n-C2-C6-alkynyl, CH(=0), C(=0)Ci-C6-al- kyl, C(=0)C2-C6-alkenyl, C(=0)C2-C6-alkynyl, C(=0)C3-C6-cycloalkyl, C(=0)N H(Ci-C6- alkyl), CH(=S), C(=S)Ci-C6-alkyl, C(=S)C2-C6-alkenyl, C(=S)C2-C6-alkynyl, C(=S)C3-C6- cycloalkyl, C(=S)N H(Ci-C6-alkyl), Ci-C6-alkyl, d-Ce-halogenalkyl, C2-C6-alkenyl, C2-C6- alkynyl, ORY, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N , O and S; wherein Rx and n is as defined above;
RY is Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6- alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, phenyl and phenyl-Ci-C6-alkyl; wherein the phenyl groups are unsubstituted or or carry one, two, three, four or five substituents selected from the group consisting of CN , halogen, OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4- halogenalkoxy;
wherein the acyclic moieties of R4 are unsubstituted or substituted with groups R4a which independently of one another are selected from:
R4a halogen, OH , CN , d-Ce-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4- halogenalkoxy, Ci-C6-alkylthio, phenoxy; wherein the phenoxy group is unsubstituted or substituted with substituent R41 a selected from the group consisting of halogen, OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogen- alkoxy;
wherein the carbocyclic, heteroaryl and aryl moieties of R4 are unsubstituted or substituted with groups R4b which independently of one another are selected from:
R4b halogen, OH , CN , Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio.
According to one embodiment of the invention the novel compounds of the formula I having R1 , R2, R3, R5, R6, A, B, R7, R8 and R9 as defined above and
R4 is in each case independently selected from halogen, OH , CN , N02, SH , N H2, N H(Ci-C4- alkyl), N(Ci-C4-alkyl)2, N H(C2-C4-alkenyl), N (C2-C4-alkenyl)2, N H(C2-C4-alkynyl), N (C2-C4- alkynyl)2, N H(C3-C6-cycloalkyl), N (C3-C6-cycloalkyl)2, N(Ci-C4-alkyl)(C2-C4-alkenyl), N (Ci- C4-alkyl)(C2-C4-alkynyl), N (Ci-C4-alkyl)(C3-C6-cycloalkyl), N (C2-C4-alkenyl)(C2-C4-al- kynyl), N(C2-C4-alkenyl)(C3-C6-cycloalkyl), N (C2-C4-alkynyl)(C3-C6-cycloalkyl),
NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, S(0)n-Ci-C6-alkyl, S(0)n-aryl, d-Ce-cycloalkylthio, S(0)n-C2-C6-alkenyl, S(0)n-C2-C6-alkynyl, CH(=0), C(=0)Ci-C6-al- kyl, C(=0)C2-C6-alkenyl, C(=0)C2-C6-alkynyl, C(=0)C3-C6-cycloalkyl, CH(=S),
Ce-alkyl, C(=S)C2-C6-alkenyl, C(=S)C2-C6-alkynyl, C(=S)C3-C6-cycloalkyl, C(=S)NH(Ci- Ce-alkyl), Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, ORY, C3-C6-cy- cloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; wherein Rx and n is as defined above;
RY is Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6- alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, phenyl and phenyl-Ci-C6-alkyl; wherein the phenyl groups are unsubstituted or or carry one, two, three, four or five substituents selected from the group consisting of CN, halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and C1-C4- halogenalkoxy;
wherein the acyclic moieties of R4 are unsubstituted or substituted with groups R4a which independently of one another are selected from:
R4a halogen, OH, CN, d-Ce-alkoxy, Cs-Ce-cycloalkyl, Cs-Ce-halogencycloalkyl, C1-C4- halogenalkoxy, Ci-C6-alkylthio, aryl and phenoxy; wherein the aryl and phenoxy group is unsubstituted or substituted with substituent R41a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the carbocyclic, heteroaryl and aryl moieties of R4 are unsubstituted or substituted with groups R4b which independently of one another are selected from:
R4b halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio.
According to one embodiment of the invention the novel compounds of the formula I having R1, R2, R3, R4, A, B, R7, R8 and R9 as defined above and
R5, R6 together with the carbon atoms to which they are bound form a phenyl or five- or six membered heteroaryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S, and wherein the phenyl or heteroaryl is substituted with (R56)0, wherein
o is 0, 1 , 2 or 3; and
R56 are independently selected from halogen, OH, CN, N02, SH, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, CH(=0),
Ce-alkyl, C(=0)NH(Ci-C6-alkyl), CR'=NOR", Ci-C6-alkyl, Ci-C6-halogenalkyl, C2- C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, S(0)n-Ci-C6-alkyl, three-, four-, five- or six-membered saturated or partially unsaturated heterocycle, five- or six-membered heteroaryl and phenyl; wherein the heterocycle or heteroaryl
contains one, two or three heteroatoms selected from N, O and S; wherein n and Rx are as defined above;
wherein R' and R" are independently selected from H , Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl or aryl; wherein the heterocycle or heteroaryl contains one, two or three heteroatoms selected from N, O and S, and wherein R' and R" are independently unsubstituted or substituted with R'" which is independently selected from halogen, OH , CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH-SO2- Rx, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6- alkynyl, C2-C6-halogenalkynyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, C3-C6-cycloal- kyl, C3-C6-halogencycloalkyl and phenyl; wherein Rx is defined above;
and
wherein the acyclic moieties of R56 are not further substituted or carry 1 , 2, 3 or up to the maximum possible number of identical or different groups R56a which independently of one another are selected from:
R56a halogen, OH, CN , Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6- halogencycloalkyl, C3-C6-halogencycloalkenyl, Ci-C4-halogenalkoxy, Ci-C6-al- kylthio, five- or six-membered heteroaryl, phenyl and phenoxy; wherein the heteroaryl, phenyl and phenoxy group is unsubstituted or unsubstituted or substituted with R561a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the carbocyclic, phenyl, heterocyclic and heteroaryl moieties of R56 are unsubstituted or substituted with identical or different groups R56b which independently of one another are selected from:
R56b halogen, OH, CN , Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, and Ci-C6-alkylthio. According to one embodiment of the invention the novel compounds of the formula I having R1 , R2, R3, R4, A, B, R7, R8 and R9 as defined above and
R5, R6 together with the carbon atoms to which they are bound form a phenyl or five- or six membered heteroaryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S, and wherein the phenyl or heteroaryl is substituted with (R56)0, wherein
o is 0, 1 , 2 or 3; and
R56 are independently selected from halogen, OH , CN, N02, SH, CH(=0), C(=0)Ci- Ce-alkyl, C(=0)N H(Ci-C6-alkyl), CR'=NOR", Ci-C6-alkyl, Ci-C6-halogenalkyl, C2- C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, S(0)n-Ci-C6-alkyl, three-, four-, five- or six-membered saturated or partially unsaturated heterocycle, five- or six-membered heteroaryl and phenyl; wherein the heterocycle or heteroaryl
contains one, two or three heteroatoms selected from N , O and S; wherein n and Rx are as defined above;
wherein R' and R" are independently selected from H , Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl or aryl; wherein the heterocycle or heteroaryl contains one, two or three heteroatoms selected from N , O and S, and wherein R' and R" are independently unsubstituted or substituted with R'" which is independently selected from halogen, OH , CN , N02, SH , N H2, N H(Ci-C4-alkyl), N(Ci-C4-alkyl)2, N H-SO2- Rx, d-Ce-alkyl, d-Ce-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6- alkynyl, C2-C6-halogenalkynyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, C3-C6-cycloal- kyl, C3-C6-halogencycloalkyl and phenyl; wherein Rx is defined above;
and
wherein the acyclic moieties of R56 are not further substituted or carry 1 , 2, 3 or up to the maximum possible number of identical or different groups R56a which independently of one another are selected from:
R56a halogen, OH , CN , Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6- halogencycloalkyl, C3-C6-halogencycloalkenyl, Ci-C4-halogenalkoxy, Ci-C6-al- kylthio, five- or six-membered heteroaryl, phenyl and phenoxy; wherein the het- eroaryl, phenyl and phenoxy group is unsubstituted or unsubstituted or substituted with R561 a selected from the group consisting of halogen, OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the carbocyclic, phenyl, heterocyclic and heteroaryl moieties of R56 are unsubstituted or substituted with identical or different groups R56b which independently of one another are selected from:
R56b halogen, OH , CN , Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6- halogencycloalkyl, Ci-C4-halogenalkoxy, and Ci-C6-alkylthio.
Particular embodiments of the compounds I are the following compounds: l-A, l-B, l-C, l-D, l-E, l-F, l-G. In these formulae, the substituents B, R4, R3 are independently as defined in claim 1 or preferably defined below:
Preferred embodiments of the present invention are the following compounds I.A-1 , I.A-2, I.A-3, I.A-4J.A-5, I.A-6, I.A-7, l-A-8; I.B-1 , I.B-2, I.B-3, I.B-4, I.B-5, I.B-6, I.B-7, I.B-8; I.C-1 , I.C-2, I.C-3, I.C-4 I.C-5, I.C-6, I.C-7, I.C-8; I.D-1 , I.D-2, I.D-3, I.D-4, I.D-5, I.D-6, I.D-7, I.D-8; I.E-1 , I.E-2, I.E- 3, I.E-4, I.E-5, I.E-6, I.E-7, I.E-8; I.F-1 , I.F-2, I.F-3, I.F-4, I.F-5, I.F-6, I.F-7, I.F-8; I.G-1 , I.G-2, I.G-3, I.G-4, I.G-5, I.G-6, I.G-7, I.G-8. In these formulae, the substituents R3, R4, R7 and R8 are independently as defined above or preferably defined herein:
I.F-4 I. G-4
I.F-5 I.G-5
I.G-6
I.F-7 I.G-7
I.F-8 I.G-8
Table 1-1 Compounds of the formula I.A-1, I.B-1, I.C-1, I.D-1, I.E-1, I.F-1, I.G-1 in which R3 is CH3 and the meaning for the combination of R4, R7 and R8 for each individual compound corresponds in each case to one line of Table A (compounds I.A-1.1-1.A-1 to I. A-1.1-1.A-450, com- pounds I.B-1.1-1.A-1 to I.B-1.1-1.A-450, compounds I.C-1.1-1.A-1 to I.C-1.1-1.A-450, compounds I.D-1.1-1.A-1 to I.D-1.1-1.A-450, compounds I.E-1.1-1.A-1 to I.E-1.1-1.A-450, compounds I.F-1.1-1.A-1 to I.F-1.1-1.A-450, compounds I.G-1.1-1.A-1 to I.G-1.1-1.A-450).
Table 1-2 Compounds of the formula I.A-1, I.B-1, I.C-1, I.D-1, I.E-1, I.F-1, I.G-1 in which R3 is CH2F and the meaning for the combination of R4, R7 and R8 for each individual compound corre- sponds in each case to one line of Table A (compounds I.A-1.1-2.A-1 to I.A-1.1-2.A-450, compounds I.B-1.1-2.A-1 to I.B-1.1-2. A-450, compounds I.C-1.1-2.A-1 to I.C-1.1-2.A-450, compounds I.D-1.1-2.A-1 to I.D-1.1-2.A 50, compounds I.E-1.1-2.A-1 to I.E-1.1-2. A-450, compounds I.F-1.1-2.A-1 to I.F-1.1-2.A-450, compounds I.G-1.1-2.A-1 to I.G-1.1-2.A-450).
Table 1-3 Compounds of the formula I.A-1, I.B-1, I.C-1, I.D-1, I.E-1, I.F-1, I.G-1 in which R3 is
CHF2 and the meaning for the combination of R4, R7and R8for each individual compound corresponds in each case to one line of Table A (compounds I.A-1.1-3.A-1 to I.A-1.1-3.A-450, compounds I.B-1.1-3.A-1 to I.B-1.1-3.A-450, compounds I.C-1.1-3.A-1 to I.C-1.1-3.A-450, compounds I.D-1.1-3.A-1 to I.D-1.1-3.A-450, compounds I.E-1.1-3.A-1 to I.E-1.1-3.A-450, com- pounds I.F-1.1-3.A-1 to I.F-1.1-3.A-450, compounds I.G-1.1 -3.A-1 to I.G-1.1-3.A-450).
Table 1-4 Compounds of the formula I.A-1, I.B-1, I.C-1, I.D-1, I.E-1, I.F-1, I.G-1 in which R3 is CF3 and the meaning for the combination of R4, R7and R8for each individual compound corresponds in each case to one line of Table A (compounds I.A-1.1-4.A-1 to I.A-1.1-4.A-450, compounds I.B-1.1-4.A-1 to I.B-1.1-4.A-450, compounds I.C-1.1-4.A-1 to I.C-1.1-4.A-450, com- pounds I.D-1.1-4.A-1 to I.D-1.1-4.A-450, compounds I.E-1.1-4.A-1 to I.E-1.1-4. A-450, compounds I.F-1.1-4.A-1 to I.F-1.1-4.A-450, compounds I.G-1.1-4.A-1 to I.G-1.1-4.A-450).
Table 1-5 Compounds of the formula I.A-1, I.B-1, I.C-1, I.D-1, I.E-1, I.F-1, I.G-1 in which R3 is CI and the meaning for the combination of R4, R7and R8 for each individual compound corresponds in each case to one line of Table A (compounds I.A-1.1-5.A-1 to I.A-1.1-5.A-450, com- pounds I.B-1.1-5.A-1 to I.B-1.1-5.A-450, compounds I.C-1.1-5.A-1 to I.C-1.1-5.A-450, compounds I.D-1.1-5.A-1 to I.D-1.1-5.A-450, compounds I.E-1.1-5.A-1 to I.E-1.1-5.A-450, compounds I.F-1.1-5.A-1 to I.F-1.1-5.A-450, compounds I.G-1.1-5.A-1 to I.G-1.1-5.A-450).
Table 1-6 Compounds of the formula I.A-1, I.B-1, I.C-1, I.D-1, I.E-1, I.F-1, I.G-1 in which R3 is OCH3 and the meaning for the combination of R4, R7and R8for each individual compound corre- sponds in each case to one line of Table A (compounds I.A-1.1-6.A-1 to I.A-1.1-6.A-450, compounds I.B-1.1-6.A-1 to I.B-1.1-6.A-450, compounds I.C-1.1-6.A-1 to I.C-1.1-6.A-450, compounds I.D-1.1-6.A-1 to I.D-1.1-6.A-450, compounds I.E-1.1-6.A-1 to I.E-1.1-6.A-450, compounds I.F-1.1-6.A-1 to I.F-1.1-6.A-450, compounds I.G-1.1-6.A-1 to I.G-1.1-6.A-450).
Table 2-1 Compounds of the formula I.A-2, I.B-2, I.C-2, I.D-2, I.E-2, I.F-2, I.G-2 in which R3 is CH3 and the meaning for the combination of R4, R7and R8for each individual compound corresponds in each case to one line of Table A (compounds I.A-2.2-1.A-1 to I.A-2.2-1.A-450, compounds I.B-2.2-1.A-1 to I.B-2.2-1.A-450, compounds I.C-2.2-1.A-1 to I.C-2.2-1.A-450, compounds I.D-2.2-1.A-1 to I.D-2.2-1.A-450, compounds I.E-2.2-1.A-1 to I.E-2.2-1.A-450, compounds I.F-2.2-1.A-1 to I.F-2.2-1.A-450, compounds I.G-2.2-1.A-1 to I.G-2.2-1.A-450).
Table 2-2 Compounds of the formula I.A-2, I.B-2, I.C-2, I.D-2, I.E-2, I.F-2, I.G-2 in which R3 is CH2F and the meaning for the combination of R4, R7 and R8 for each individual compound corresponds in each case to one line of Table A (compounds I.A-2.2-2.A-1 to I.A-2.2-2.A-450, compounds I.B-2.2-2.A-1 to I.B-2.2-2. A-450, compounds I.C-2.2-2.A-1 to I.C-2.2-2.A-450, compounds I.D-2.2-2.A-1 to I.D-2.2-2.A-450, compounds I.E-2.2-2.A-1 to I.E-2.2-2. A-450, com- pounds I.F-2.2-2.A-1 to I.F-2.2-2.A-450, compounds I.G-2.2-2.A-1 to I.G-2.2-2.A-450).
Table 2-3 Compounds of the formula I.A-2, I.B-2, I.C-2, I.D-2, I.E-2, I.F-2, I.G-2 in which R3 is CHF2 and the meaning for the combination of R4, R7and R8for each individual compound corresponds in each case to one line of Table A (compounds I.A-2.2-3.A-1 to I.A-2.2-3.A-450, compounds I.B-2.2-3.A-1 to I.B-2.2-3.A-450, compounds I.C-2.2-3.A-1 to I.C-2.2-3.A-450, com- pounds I.D-2.2-3.A-1 to I.D-2.2-3.A-450, compounds I.E-2.2-3.A-1 to I.E-2.2-3. A-450, compounds I.F-2.2-3.A-1 to I.F-2.2-3.A-450, compounds I.G-2.2-3.A-1 to I.G-2.2-3.A-450).
Table 2-4 Compounds of the formula I.A-2, I.B-2, I.C-2, I.D-2, I.E-2, I.F-2, I.G-2 in which R3 is
CF3 and the meaning for the combination of R4, R7 and R8 for each individual compound corresponds in each case to one line of Table A (compounds I.A-2.2-4.A-1 to I.A-2.2-4.A-450, compounds I.B-2.2-4.A-1 to I. B-2.2-4. A-450, compounds I.C-2.2-4.A-1 to I.C-2.2-4.A-450, compounds I.D-2.2-4.A-1 to I.D-2.2-4.A-450, compounds I.E-2.2-4.A-1 to I. E-2.2-4. A-450, com- pounds I.F-2.2-4.A-1 to I.F-2.2-4.A-450, compounds I.G-2.2-4.A-1 to I.G-2.2-4.A-450).
Table 2-5 Compounds of the formula I.A-2, I. B-2, I.C-2, I.D-2, I. E-2, I.F-2, I.G-2 in which R3 is CI and the meaning for the combination of R4, R7 and R8 for each individual compound corresponds in each case to one line of Table A (compounds I.A-2.2-5.A-1 to I.A-2.2-5.A-450, compounds I.B-2.2-5.A-1 to I.B-2.2-5.A-450, compounds I.C-2.2-5.A-1 to I.C-2.2-5.A-450, com- pounds I.D-2.2-5.A-1 to I.D-2.2-5.A-450, compounds I.E-2.2-5.A-1 to I.E-2.2-5.A-450, compounds I.F-2.2-5.A-1 to I.F-2.2-5.A-450, compounds I.G-2.2-5.A-1 to I.G-2.2-5.A-450).
Table 2-6 Compounds of the formula I.A-2, I. B-2, I.C-2, I.D-2, I. E-2, I.F-2, I.G-2 in which R3 is OCH3 and the meaning for the combination of R4, R7 and R8for each individual compound corresponds in each case to one line of Table A (compounds I.A-2.2-6.A-1 to I.A-2.2-6.A-450, com- pounds I.B-2.2-6.A-1 to I.B-2.2-6.A-450, compounds I.C-2.2-6.A-1 to I.C-2.2-6.A-450, compounds I.D-2.2-6.A-1 to I.D-2.2-6.A-450, compounds I.E-2.2-6.A-1 to I.E-2.2-6.A-450, compounds I.F-2.2-6.A-1 to I.F-2.2-6.A-450, compounds I.G-2.2-6.A-1 to I.G-2.2-6.A-450).
Table 3-1 Compounds of the formula I.A-3, I.B-3, I.C-3, I.D-3, I.E-3, I.F-3, I.G-3 in which R3 is CH3 and the meaning for the combination of R4, R7 and R8 for each individual compound corre- sponds in each case to one line of Table A (compounds I.A-3.3-1 .A-1 to I.A-3.3-1.A-450, compounds I.B-3.3-1.A-1 to I.B-3.3-1 .A-450, compounds I.C-3.3-1 .A-1 to I.C-3.3-1 .A-450, compounds I.D-3.3-1 .A-1 to I.D-3.3-1 .A-450, compounds I.E-3.3-1.A-1 to I.E-3.3-1 .A-450, compounds I.F-3.3-1 .A-1 to I.F-3.3-1.A-450, compounds I.G-3.3-1.A-1 to I.G-3.3-1.A-450).
Table 3-2 Compounds of the formula I.A-3, I.B-3, I.C-3, I.D-3, I.E-3, I.F-3, I.G-3 in which R3 is CH2F and the meaning for the combination of R4, R7 and R8 for each individual compound corresponds in each case to one line of Table A (compounds I.A-3.3-2.A-1 to I.A-3.3-2.A-450, compounds I.B-3.3-2.A-1 to I.B-3.3-2.A-450, compounds I.C-3.3-2.A-1 to I.C-3.3-2.A-450, compounds I.D-3.3-2.A-1 to I.D-3.3-2. A-450, compounds I.E-3.3-2.A-1 to I.E-3.3-2.A-450, compounds I.F-3.3-2.A-1 to I.F-3.3-2. A-450, compounds I.G-3.3-2.A-1 to I.G-3.3-2.A-450).
Table 3-3 Compounds of the formula I.A-3, I.B-3, I.C-3, I.D-3, I.E-3, I.F-3, I.G-3 in which R3 is CHF2 and the meaning for the combination of R4, R7 and R8for each individual compound corresponds in each case to one line of Table A (compounds I.A-3.3-3.A-1 to I.A-3.3-3.A-450, compounds I.B-3.3-3.A-1 to I.B-3.3-3.A-450, compounds I.C-3.3-3.A-1 to I.C-3.3-3.A-450, compounds I.D-3.3-3.A-1 to I.D-3.3-3. A-450, compounds I.E-3.3-3.A-1 to I.E-3.3-3.A-450, com- pounds I.F-3.3-3.A-1 to I.F-3.3-3.A-450, compounds I.G-3.3-3.A-1 to I.G-3.3-3.A-450).
Table 3-4 Compounds of the formula I.A-3, I.B-3, I.C-3, I.D-3, I.E-3, I.F-3, I.G-3 in which R3 is CF3 and the meaning for the combination of R4, R7 and R8for each individual compound corresponds in each case to one line of Table A (compounds I.A-3.3-4.A-1 to I.A-3.3-4.A-450, compounds I.B-3.3-4.A-1 to I.B-3.3-4.A-450, compounds I.C-3.3-4.A-1 to I.C-3.3-4.A-450, com- pounds I.D-3.3-4.A-1 to I.D-3.3-4. A-450, compounds I.E-3.3-4.A-1 to I.E-3.3-4.A-450, compounds I.F-3.3-4.A-1 to I.F-3.3-4. A-450, compounds I.G-3.3-4.A-1 to I.G-3.3-4.A-450).
Table 3-5 Compounds of the formula I.A-3, I.B-3, I.C-3, I.D-3, I.E-3, I.F-3, I.G-3 in which R3 is
CI and the meaning for the combination of R4, R7 and R8 for each individual compound corresponds in each case to one line of Table A (compounds I.A-3.3-5.A-1 to I.A-3.3-5.A-450, compounds I.B-3.3-5.A-1 to I.B-3.3-5.A-450, compounds I.C-3.3-5.A-1 to I.C-3.3-5.A-450, compounds I.D-3.3-5.A-1 to I.D-3.3-5.A-450, compounds I.E-3.3-5.A-1 to I.E-3.3-5.A-450, com- pounds I.F-3.3-5.A-1 to I.F-3.3-5.A-450, compounds I.G-3.3-5.A-1 to I.G-3.3-5.A-450).
Table 3-6 Compounds of the formula I.A-3, I.B-3, I.C-3, I.D-3, I.E-3, I.F-3, I.G-3 in which R3 is OCH3 and the meaning for the combination of R4, R7 and R8 for each individual compound corresponds in each case to one line of Table A (compounds I.A-3.3-6.A-1 to I.A-3.3-6.A-450, compounds I.B-3.3-6.A-1 to I.B-3.3-6.A-450, compounds I.C-3.3-6.A-1 to I.C-3.3-6.A-450, com- pounds I.D-3.3-6.A-1 to I.D-3.3-6. A-450, compounds I.E-3.3-6.A-1 to I.E-3.3-6.A-450, compounds I.F-3.3-6.A-1 to I.F-3.3-6.A-450, compounds I.G-3.3-6.A-1 to I.G-3.3-6.A-450).
Table 4-1 Compounds of the formula I.A-4, I.B-4, I.C-4, I.D-4, I.E-4, I.F-4, I.G-4 in which R3 is CH3 and the meaning for the combination of R4, R7 and R8for each individual compound corre- sponds in each case to one line of Table A (compounds I.A-4.4-1 .A-1 to I.A-4.4-1.A-450, compounds I.B-4.4-1.A-1 to I.B-4.4-1 .A-450, compounds I.C-4.4-1 .A-1 to I.C-4.4-1 .A-450, compounds I.D-4.4-1 .A-1 to I.D-4.4-1 .A-450, compounds I.E-4.4-1.A-1 to I.E-4.4-1 .A-450, compounds I.F-4.4-1 .A-1 to I.F-4.4-1.A-450, compounds I.G-4.4-1.A-1 to I.G-4.4-1.A-450).
Table 4-2 Compounds of the formula I.A-4, I.B-4, I.C-4, I.D-4, I.E-4, I.F-4, I.G-4 in which R3 is CH2F and the meaning for the combination of R4, R7 and R8 for each individual compound corresponds in each case to one line of Table A (compounds I.A-4.4-2.A-1 to I.A-4.4-2.A-450, compounds I.B-4.4-2.A-1 to I.B-4.4-2. A-450, compounds I.C-4.4-2.A-1 to I.C-4.4-2.A-450, compounds I.D-4.4-2.A-1 to I.D-4.4-2.A-450, compounds I.E-4.4-2.A-1 to I.E-4.4-2. A-450, compounds I.F-4.4-2.A-1 to I.F-4.4-2.A-450, compounds I.G-4.4-2.A-1 to I.G-4.4-2.A-450).
Table 4-3 Compounds of the formula I.A-4, I.B-4, I.C-4, I.D-4, I.E-4, I.F-4, I.G-4 in which R3 is CHF2 and the meaning for the combination of R4, R7 and R8for each individual compound corresponds in each case to one line of Table A (compounds I.A-4.4-3.A-1 to I.A-4.4-3.A-450, compounds I.B-4.4-3.A-1 to I.B-4.4-3.A-450, compounds I.C-4.4-3.A-1 to I.C-4.4-3.A-450, compounds I.D-4.4-3.A-1 to I.D-4.4-3.A-450, compounds I.E-4.4-3.A-1 to I.E-4.4-3. A-450, com- pounds I.F-4.4-3.A-1 to I.F-4.4-3.A-450, compounds I.G-4.4-3.A-1 to I.G-4.4-3.A-450).
Table 4-4 Compounds of the formula I.A-4, I.B-4, I.C-4, I.D-4, I.E-4, I.F-4, I.G-4 in which R3 is CF3 and the meaning for the combination of R4, R7 and R8 for each individual compound corresponds in each case to one line of Table A (compounds I.A-4.4-4.A-1 to I.A-4.4-4.A-450, compounds I.B-4.4-4.A-1 to I.B-4.4-4. A-450, compounds I.C-4.4-4.A-1 to I.C-4.4-4.A-450, com- pounds I.D-4.4-4.A-1 to I.D-4.4-4.A-450, compounds I.E-4.4-4.A-1 to I.E-4.4-4. A-450, compounds I.F-4.4-4.A-1 to I.F-4.4-4.A-450, compounds I.G-4.4-4.A-1 to I.G-4.4-4.A-450).
Table 4-5 Compounds of the formula I.A-4, I.B-4, I.C-4, I.D-4, I.E-4, I.F-4, I.G-4 in which R3 is CI and the meaning for the combination of R4, R7 and R8 for each individual compound corresponds in each case to one line of Table A (compounds I.A-4.4-5.A-1 to I.A-4.4-5.A-450, com- pounds I.B-4.4-5.A-1 to I.B-4.4-5.A-450, compounds I.C-4.4-5.A-1 to I.C-4.4-5.A-450, compounds I.D-4.4-5.A-1 to I.D-4.4-5.A-450, compounds I.E-4.4-5.A-1 to I.E-4.4-5.A-450, compounds I.F-4.4-5.A-1 to I.F-4.4-5.A-450, compounds I.G-4.4-5.A-1 to I.G-4.4-5.A-450).
Table 4-6 Compounds of the formula I.A-4, I.B-4, I.C-4, I.D-4, I.E-4, I.F-4, I.G-4 in which R3 is OCH3 and the meaning for the combination of R4, R7 and R8for each individual compound corresponds in each case to one line of Table A (compounds I.A-4.4-6.A-1 to I.A-4.4-6.A-450, compounds I.B-4.4-6.A-1 to I.B-4.4-6.A-450, compounds I.C-4.4-6.A-1 to I.C-4.4-6.A-450, com- pounds I.D-4.4-6.A-1 to I.D-4.4-6.A-450, compounds I.E-4.4-6.A-1 to I.E-4.4-6.A-450, compounds I.F-4.4-6.A-1 to I.F-4.4-6.A-450, compounds I.G-4.4-6.A-1 to I.G-4.4-6.A-450).
Table 5-1 Compounds of the formula I.A-5, I.B-5, I.C-5, I.D-5, I.E-5, I.F-5, I.G-5 in which R3 is CH3 and the meaning for the combination of R4, R7 and R8 for each individual compound corresponds in each case to one line of Table A (compounds I.A-5.5-1 .A-1 to I.A-5.5-1.A-450, com- pounds I.B-5.5-1.A-1 to I.B-5.5-1 .A-450, compounds I.C-5.5-1 .A-1 to I.C-5.5-1 .A-450, compounds I.D-5.5-1 .A-1 to I.D-5.5-1 .A-450, compounds I.E-5.5-1.A-1 to I.E-5.5-1 .A-450, compounds I.F-5.5-1 .A-1 to I.F-5.5-1.A-450, compounds I.G-5.5-1.A-1 to I.G-5.5-1.A-450).
Table 5-2 Compounds of the formula I.A-5, I.B-5, I.C-5, I.D-5, I.E-5, I.F-5, I.G-5 in which R3 is CH2F and the meaning for the combination of R4, R7 and R8 for each individual compound corre- sponds in each case to one line of Table A (compounds I.A-5.5-2.A-1 to I.A-5.5-2.A-450, compounds I.B-5.5-2.A-1 to I.B-5.5-2.A-450, compounds I.C-5.5-2.A-1 to I.C-5.5-2.A-450, compounds I.D-5.5-2.A-1 to I.D-5.5-2. A-450, compounds I.E-5.5-2.A-1 to I.E-5.5-2.A-450, compounds I.F-5.5-2.A-1 to I.F-5.5-2.A-450, compounds I.G-5.5-2.A-1 to I.G-5.5-2.A-450).
Table 5-3 Compounds of the formula I.A-5, I.B-5, I.C-5, I.D-5, I.E-5, I.F-5, I.G-5 in which R3 is CHF2 and the meaning for the combination of R4, R7 and R8for each individual compound corresponds in each case to one line of Table A (compounds I.A-5.5-3.A-1 to I.A-5.5-3.A-450, compounds I.B-5.5-3.A-1 to I.B-5.5-3.A-450, compounds I.C-5.5-3.A-1 to I.C-5.5-3.A-450, compounds I.D-5.5-3.A-1 to I.D-5.5-3. A-450, compounds I.E-5.5-3.A-1 to I.E-5.5-3.A-450, compounds I.F-5.5-3.A-1 to I.F-5.5-3.A-450, compounds I.G-5.5-3.A-1 to I.G-5.5-3.A-450).
Table 5-4 Compounds of the formula I.A-5, I.B-5, I.C-5, I.D-5, I.E-5, I.F-5, I.G-5 in which R3 is CF3 and the meaning for the combination of R4, R7 and R8for each individual compound corresponds in each case to one line of Table A (compounds I.A-5.5-4.A-1 to I.A-5.5-4.A-450, compounds I.B-5.5-4.A-1 to I.B-5.5-4.A-450, compounds I.C-5.5-4.A-1 to I.C-5.5-4.A-450, compounds I.D-5.5-4.A-1 to I.D-5.5-4. A-450, compounds I.E-5.5-4.A-1 to I.E-5.5-4.A-450, com- pounds I.F-5.5-4.A-1 to I.F-5.5-4.A-450, compounds I.G-5.5-4.A-1 to I.G-5.5-4.A-450).
Table 5-5 Compounds of the formula I.A-5, I.B-5, I.C-5, I.D-5, I.E-5, I.F-5, I.G-5 in which R3 is CI and the meaning for the combination of R4, R7 and R8 for each individual compound corresponds in each case to one line of Table A (compounds I.A-5.5-5.A-1 to I.A-5.5-5.A-450, compounds I.B-5.5-5.A-1 to I.B-5.5-5.A-450, compounds I.C-5.5-5.A-1 to I.C-5.5-5.A-450, com- pounds I.D-5.5-5.A-1 to I.D-5.5-5. A-450, compounds I.E-5.5-5.A-1 to I.E-5.5-5.A-450, compounds I.F-5.5-5.A-1 to I.F-5.5-5.A-450, compounds I.G-5.5-5.A-1 to I.G-5.5-5.A-450).
Table 5-6 Compounds of the formula I.A-5, I.B-5, I.C-5, I.D-5, I.E-5, I.F-5, I.G-5 in which R3 is OCH3 and the meaning for the combination of R4, R7 and R8 for each individual compound corresponds in each case to one line of Table A (compounds I.A-5.5-6.A-1 to I.A-5.5-6.A-450, com- pounds I.B-5.5-6.A-1 to I.B-5.5-6.A-450, compounds I.C-5.5-6.A-1 to I.C-5.5-6.A-450, compounds I.D-5.5-6.A-1 to I.D-5.5-6. A-450, compounds I.E-5.5-6.A-1 to I.E-5.5-6.A-450, compounds I.F-5.5-6.A-1 to I.F-5.5-6.A-450, compounds I.G-5.5-6.A-1 to I.G-5.5-6.A-450).
Table 6-1 Compounds of the formula I.A-6, I.B-6, I.C-6, I.D-6, I.E-6, I.F-6, I.G-6 in which R3 is CH3 and the meaning for the combination of R4, R7 and R8 for each individual compound corresponds in each case to one line of Table A (compounds I.A-6.6-1 .A-1 to I.A-6.6-1.A-450, compounds I.B-6.6-1.A-1 to I.B-6.6-1 .A-450, compounds I.C-6.6-1 .A-1 to I.C-6.6-1 .A-450, com- pounds I.D-6.6-1 .A-1 to I.D-6.6-1 .A-450, compounds I.E-6.6-1.A-1 to I.E-6.6-1 .A-450, compounds I.F-6.6-1 .A-1 to I.F-6.6-1.A-450, compounds I.G-6.6-1.A-1 to I.G-6.6-1.A-450).
Table 6-2 Compounds of the formula I.A-6, I.B-6, I.C-6, I.D-6, I.E-6, I.F-6, I.G-6 in which R3 is CH2F and the meaning for the combination of R4, R7 and R8 for each individual compound corresponds in each case to one line of Table A (compounds I.A-6.6-2.A-1 to I.A-6.6-2.A-450, com- pounds I.B-6.6-2.A-1 to I.B-6.6-2. A-450, compounds I.C-6.6-2.A-1 to I.C-6.6-2.A-450, compounds I.D-6.6-2.A-1 to I.D-6.6-2. A-450, compounds I.E-6.6-2.A-1 to I.E-6.6-2.A-450, compounds I.F-6.6-2.A-1 to I.F-6.6-2.A-450, compounds I.G-6.6-2.A-1 to I.G-6.6-2.A-450).
Table 6-3 Compounds of the formula I.A-6, I.B-6, I.C-6, I.D-6, I.E-6, I.F-6, I.G-6 in which R3 is CHF2 and the meaning for the combination of R4, R7 and R8for each individual compound corre- sponds in each case to one line of Table A (compounds I.A-6.6-3.A-1 to I.A-6.6-3.A-450, compounds I.B-6.6-3.A-1 to I.B-6.6-3.A-450, compounds I.C-6.6-3.A-1 to I.C-6.6-3.A-450, compounds I.D-6.6-3.A-1 to I.D-6.6-3. A-450, compounds I.E-6.6-3.A-1 to I.E-6.6-3.A-450, compounds I.F-6.6-3.A-1 to I.F-6.6-3.A-450, compounds I.G-6.6-3.A-1 to I.G-6.6-3.A-450).
Table 6-4 Compounds of the formula I.A-6, I.B-6, I.C-6, I.D-6, I.E-6, I.F-6, I.G-6 in which R3 is CF3 and the meaning for the combination of R4, R7 and R8 for each individual compound corresponds in each case to one line of Table A (compounds I.A-6.6-4.A-1 to I.A-6.6-4.A-450, compounds I.B-6.6-4.A-1 to I.B-6.6-4.A-450, compounds I.C-6.6-4.A-1 to I.C-6.6-4.A-450, compounds I.D-6.6-4.A-1 to I.D-6.6-4. A-450, compounds I.E-6.6-4.A-1 to I.E-6.6-4.A-450, compounds I.F-6.6-4.A-1 to I.F-6.6-4.A-450, compounds I.G-6.6-4.A-1 to I.G-6.6-4.A-450).
Table 6-5 Compounds of the formula I.A-6, I.B-6, I.C-6, I.D-6, I.E-6, I.F-6, I.G-6 in which R3 is CI and the meaning for the combination of R4, R7 and R8 for each individual compound corresponds in each case to one line of Table A (compounds I.A-6.6-5.A-1 to I.A-6.6-5.A-450, compounds I.B-6.6-5.A-1 to I.B-6.6-5.A-450, compounds I.C-6.6-5.A-1 to I.C-6.6-5.A-450, compounds I.D-6.6-5.A-1 to I.D-6.6-5. A-450, compounds I.E-6.6-5.A-1 to I.E-6.6-5.A-450, com- pounds I.F-6.6-5.A-1 to I.F-6.6-5.A-450, compounds I.G-6.6-5.A-1 to I.G-6.6-5.A-450).
Table 6-6 Compounds of the formula I.A-6, I.B-6, I.C-6, I.D-6, I.E-6, I.F-6, I.G-6 in which R3 is OCH3 and the meaning for the combination of R4, R7 and R8for each individual compound corresponds in each case to one line of Table A (compounds I.A-6.6-6.A-1 to I.A-6.6-6.A-450, compounds I.B-6.6-6.A-1 to I.B-6.6-6.A-450, compounds I.C-6.6-6.A-1 to I.C-6.6-6.A-450, com- pounds I.D-6.6-6.A-1 to I.D-6.6-6. A-450, compounds I.E-6.6-6.A-1 to I.E-6.6-6.A-450, compounds I.F-6.6-6.A-1 to I.F-6.6-6.A-450, compounds I.G-6.6-6.A-1 to I.G-6.6-6.A-450).
Table 7-1 Compounds of the formula I.A-7, I.B-7, I.C-7, I.D-7, I.E-7, I.F-7, I.G-7 in which R3 is CH3 and the meaning for the combination of R4, R7 and R8 for each individual compound corresponds in each case to one line of Table A (compounds I.A-7.7-1 .A-1 to I.A-7.7-1.A-450, com- pounds I.B-7.7-1.A-1 to I.B-7.7-1 .A-450, compounds I.C-7.7-1 .A-1 to I.C-7.7-1 .A-450, compounds I.D-7.7-1 .A-1 to I.D-7.7-1 .A-450, compounds I.E-7.7-1.A-1 to I.E-7.7-1 .A-450, compounds I.F-7.7-1 .A-1 to I.F-7.7-1.A-450, compounds I.G-7.7-1.A-1 to I.G-7.7-1.A-450).
Table 7-2 Compounds of the formula I.A-7, I.B-7, I.C-7, I.D-7, I.E-7, I.F-7, I.G-7 in which R3 is CH2F and the meaning for the combination of R4, R7 and R8 for each individual compound corresponds in each case to one line of Table A (compounds I.A-7.7-2.A-1 to I.A-7.7-2.A-450, compounds I.B-7.7-2.A-1 to I.B-7.7-2.A-450, compounds I.C-7.7-2.A-1 to I.C-7.7-2.A-450, com- pounds I.D-7.7-2.A-1 to I.D-7.7-2. A-450, compounds I.E-7.7-2.A-1 to I.E-7.7-2.A-450, compounds I.F-7.7-2.A-1 to I.F-7.7-2.A-450, compounds I.G-7.7-2.A-1 to I.G-7.7-2.A-450).
Table 7-3 Compounds of the formula I.A-7, I.B-7, I.C-7, I.D-7, I.E-7, I.F-7, I.G-7 in which R3 is CHF2 and the meaning for the combination of R4, R7 and R8for each individual compound corresponds in each case to one line of Table A (compounds I.A-7.7-3.A-1 to I.A-7.7-3.A-450, com- pounds I.B-7.7-3.A-1 to I.B-7.7-3.A-450, compounds I.C-7.7-3.A-1 to I.C-7.7-3.A-450, compounds I.D-7.7-3.A-1 to I.D-7.7-3. A-450, compounds I.E-7.7-3.A-1 to I.E-7.7-3.A-450, compounds I.F-7.7-3.A-1 to I.F-7.7-3.A-450, compounds I.G-7.7-3.A-1 to I.G-7.7-3.A-450).
Table 7-4 Compounds of the formula I.A-7, I.B-7, I.C-7, I.D-7, I.E-7, I.F-7, I.G-7 in which R3 is CF3 and the meaning for the combination of R4, R7 and R8for each individual compound corre- sponds in each case to one line of Table A (compounds I.A-7.7-4.A-1 to I.A-7.7-4.A-450, compounds I.B-7.7-4.A-1 to I.B-7.7-4.A-450, compounds I.C-7.7-4.A-1 to I.C-7.7-4.A-450, compounds I.D-7.7-4.A-1 to I.D-7.7-4.A-450, compounds I.E-7.7-4.A-1 to I.E-7.7-4.A-450, compounds I.F-7.7-4.A-1 to I.F-7.7-4.A-450, compounds I.G-7.7-4.A-1 to I.G-7.7-4.A-450).
Table 7-5 Compounds of the formula I.A-7, I.B-7, I.C-7, I.D-7, I.E-7, I.F-7, I.G-7 in which R3 is CI and the meaning for the combination of R4, R7 and R8for each individual compound corresponds in each case to one line of Table A (compounds I.A-7.7-5.A-1 to I.A-7.7-5.A-450, compounds I.B-7.7-5.A-1 to I.B-7.7-5.A-450, compounds I.C-7.7-5.A-1 to I.C-7.7-5.A-450, compounds I.D-7.7-5.A-1 to I.D-7.7-5. A-450, compounds I.E-7.7-5.A-1 to I.E-7.7-5.A-450, compounds I.F-7.7-5.A-1 to I.F-7.7-5.A-450, compounds I.G-7.7-5.A-1 to I.G-7.7-5.A-450).
Table 7-6 Compounds of the formula I.A-7, I.B-7, I.C-7, I.D-7, I.E-7, I.F-7, I.G-7 in which R3 is OCH3 and the meaning for the combination of R4, R7 and R8for each individual compound corresponds in each case to one line of Table A (compounds I.A-7.7-6.A-1 to I.A-7.7-6.A-450, compounds I.B-7.7-6.A-1 to I.B-7.7-6.A-450, compounds I.C-7.7-6.A-1 to I.C-7.7-6.A-450, compounds I.D-7.7-6.A-1 to I.D-7.7-6. A-450, compounds I.E-7.7-6.A-1 to I.E-7.7-6.A-450, com- pounds I.F-7.7-6.A-1 to I.F-7.7-6.A-450, compounds I.G-7.7-6.A-1 to I.G-7.7-6.A-450).
Table 8-1 Compounds of the formula I.A-8, I.B-8, I.C-8, I.D-8, I.E-8, I.F-8, I.G-8 in which R3 is CH3 and the meaning for the combination of R4 and R7for each individual compound corresponds in each case to one line of Table A (compounds I.A-8.8-1 .A-1 to I.A-8.8-1.A-90, compounds I.B-8.8-1.A-1 to I.B-8.8-1 .A-90, compounds I.C-8.8-1.A-1 to I.C-8.8-1.A-90, compounds I.D-8.8-1 .A-1 to I.D-8.8-1 .A-90, compounds I.E-8.8-1 .A-1 to I.E-8.8-1.A-90, compounds I.F-8.8- 1 .A-1 to I.F-8.8-1 .A-90, compounds I.G-8.8-1.A-1 to I.G-8.8-1.A-90).
Table 8-2 Compounds of the formula I.A-8, I.B-8, I.C-8, I.D-8, I.E-8, I.F-8, I.G-8 in which R3 is CH2F and the meaning for the combination of R4 and R7 for each individual compound corresponds in each case to one line of Table A (compounds I.A-8.8-2.A-1 to I.A-8.8-2.A-90, com- pounds I.B-8.8-2.A-1 to I.B-8.8-2.A-90, compounds I.C-8.8-2.A-1 to I.C-8.8-2.A-90, compounds
1. D-8.8-2.A-1 to I.D-8.8-2.A-90, compounds I.E-8.8-2.A-1 to I.E-8.8-2.A-90, compounds I.F-8.8-
2. A-1 to I.F-8.8-2.A-90, compounds I.G-8.8-2.A-1 to I.G-8.8-2.A-90).
Table 8-3 Compounds of the formula I.A-8, I.B-8, I.C-8, I.D-8, I.E-8, I.F-8, I.G-8 in which R3 is CHF2 and the meaning for the combination of R4 and R7 for each individual compound corresponds in each case to one line of Table A (compounds I.A-8.8-3.A-1 to I.A-8.8-3.A-90, compounds I.B-8.8-3.A-1 to I.B-8.8-3.A-90, compounds I.C-8.8-3.A-1 to I.C-8.8-3.A-90, compounds I.D-8.8-3.A-1 to I.D-8.8-3.A-90, compounds I.E-8.8-3.A-1 to I.E-8.8-3.A-90, compounds I.F-8.8-
3. A-1 to I.F-8.8-3.A-90, compounds I.G-8.8-3.A-1 to I.G-8.8-3.A-90).
Table 8-4 Compounds of the formula I.A-8, I.B-8, I.C-8, I.D-8, I.E-8, I.F-8, I.G-8 in which R3 is CF3 and the meaning for the combination of R4 and R7 for each individual compound corresponds in each case to one line of Table A (compounds I.A-8.8-4.A-1 to I.A-8.8-4.A-90, com- pounds I.B-8.8-4.A-1 to I.B-8.8-4.A-90, compounds I.C-8.8-4.A-1 to I.C-8.8-4.A-90, compounds I.D-8.8-4.A-1 to I.D-8.8-4.A-90, compounds I.E-8.8-4.A-1 to I.E-8.8-4.A-90, compounds I.F-8.8-
4. A-1 to I.F-8.8-4.A-90, compounds I.G-8.8-4.A-1 to I.G-8.8-4.A-90).
Table 8-5 Compounds of the formula I.A-8, I.B-8, I.C-8, I.D-8, I.E-8, I.F-8, I.G-8 in which R3 is CI and the meaning for the combination of R4 and R7for each individual compound corresponds in each case to one line of Table A (compounds I.A-8.8-5.A-1 to I.A-8.8-5.A-90, compounds I.B- 8.8-5.A-1 to I.B-8.8-5.A-90, compounds I.C-8.8-5.A-1 to I.C-8.8-5.A-90, compounds I.D-8.8-5.A- 1 to I.D-8.8-5.A-90, compounds I.E-8.8-5.A-1 to I.E-8.8-5.A-90, compounds I.F-8.8-5.A-1 to I.F- 8.8-5.A-90, compounds I.G-8.8-5.A-1 to I.G-8.8-5.A-90).
Table 8-6 Compounds of the formula I.A-8, I.B-8, I.C-8, I.D-8, I.E-8, I.F-8, I.G-8 in which R3 is OCH3 and the meaning for the combination of R4 and R7for each individual compound corresponds in each case to one line of Table A (compounds I.A-8.8-6.A-1 to I.A-8.8-6.A-90, compounds I.B-8.8-6.A-1 to I.B-8.8-6.A-90, compounds I.C-8.8-6.A-1 to I.C-8.8-6.A-90, compounds I.D-8.8-6.A-1 to I.D-8.8-6.A-90, compounds I.E-8.8-6.A-1 to I.E-8.8-6.A-90, compounds I.F-8.8- 6.A-1 to I.F-8.8-6.A-90, compounds I.G-8.8-6.A-1 to I.G-8.8-6.A-90).
Table A
Preferred embodiments of the present invention are further the following compounds I.H-1 , I.H- 2, I.H-3, I.H-4J.H-5, I.H-6, I.H-7, l-H-8; compounds I.H-1 , I.H-2, I.H-3, I.H-4J.H-5, I.H-6, I.H-7, I- H-8; compounds 1.1-1 , I.I-2, 1.1-3, 1.1-4,1.1-5, 1.1-6, 1.1-7, 1-1-8; compounds I.J-1 , I.J-2, I.J-3, I.J-4,I.J- 5, I.J-6, I.J-7, l-J-8; compounds I.K-1 , I.K-2, I.K-3, I.K-4J.K-5, I.K-6, I.K-7, l-K-8; compounds I.L- 1 , I.L-2, I.L-3, I.L-4J.L-5, I.L-6, I.L-7, l-L-8; compounds I.M-1 , I.M-2, I.M-3, I.M-4,I.M-5, I.M-6, I.M-7, l-M-8; compounds I.N-1 , I.N-2, I.N-3, I.N-4J.N-5, I.N-6, I.N-7, l-N-8. In these formulae, the substituents R7 and R8 are independently as defined above or preferably defined herein:
I.H-8
I.H-6 I.H-7
I.I-8
1.1-6
I.J-8
I.J-6 I.J-7
Ι.Κ-8
I.K-6 I.K-7
I.L-8
I.L-6 I.L-7
I.M-8
I.M-6 I.M-7
I.N-8
I.N-6 I.N-7
Table 9-1 Compounds of the formula compounds I.H-1 , I.H-2, I.H-3, I.H-4J.H-5, I.H-6, I.H-7, I.H-8 in which the meaning for the combination of R7 and R8for each individual compound corresponds in each case to one line of Table B (compounds I.H-1.9-1.B-1 to I.H-1.9-1.B-75, com- pounds I.H-2.9-1 .B-1 to I.H-2.9-1 .B-75, compounds I.H-3.9-1.B-1 to I.H-3.9-1.B-75, compounds I.H-4.9-1 .B-1 to I.H-4.9-1 .B-75, compounds I.H-5.9-1 .B-1 to I.H-5.9-1 .B-75, compounds I.H-6.9- 1 .B-1 to I.H-6.9-1 .B-75, compounds I.H-7.9-1 .B-1 to I.H-7.9-1 .B-75, compounds I.H-8.9-1.B-1 to I.H-8.9-1 .B-75).
Table 9-2 Compounds of the formula compounds 1.1-1 , I.I-2, I.I-3, 1.1-4 , 1.1-5, 1.1-6, 1.1-7, 1.1-8 in which the meaning for the combination of R7 and R8for each individual compound corresponds in each case to one line of Table B (compounds 1.1-1 .9-2. B-1 to 1.1-1 .9-2. B-75, compounds l.l- 2.9-2. B-1 to I.I-2.9-2.B-75, compounds I.I-3.9-2.B-1 to I.I-3.9-2.B-75, compounds I.I-4.9-2.B-1 to I.I-4.9-2.B-75, compounds I.I-5.9-2.B-1 to I.I-5.9-2.B-75, compounds I.I-6.9-2.B-1 to I.I-6.9-2.B- 75, compounds I.I-7.9-2.B-1 to I.I-7.9-2.B-75, compounds I.I-8.9-2.B-1 to I.I-8.9-2.B-75).
Table 9-3 Compounds of the formula compounds I.J-1 , I.J-2, I.J-3, I.J-4,I.J-5, I.J-6, I.J-7, I.J-8 in which the meaning for the combination of R7 and R8for each individual compound corresponds in each case to one line of Table B (compounds I.J-1.9-3. B-1 to I.J-1.9-3. B-75, compounds I.J-2.9-3.B-1 to I.J-2.9-3.B-75, compounds I.J-3.9-3.B-1 to I.J-3.9-3.B-75, compounds I.J-4.9-3.B-1 to I.J-4.9-3. B-75, compounds I.J-5.9-3.B-1 to I.J-5.9-3. B-75, compounds I.J-6.9- 3. B-1 to I.J-6.9-3. B-75, compounds I.J-7.9-3.B-1 to I.J-7.9-3. B-75, compounds I.J-8.9-3.B-1 to I.J-8.9-3.B-75).
Table 9-4 Compounds of the formula compounds I.K-1 , I.K-2, I.K-3, I.K-4 .K-5, I.K-6, I.K-7, I.K-8 in which the meaning for the combination of R7and R8for each individual compound corresponds in each case to one line of Table B (compounds I.K-1.9-4. B-1 to I.K-1.9-4. B-75, compounds I.K-2.9-4. B-1 to I.K-2.9-4. B-75, compounds I.K-3.9-4. B-1 to I.K-3.9-4. B-75, compounds I.K-4.9-4.B-1 to I.K-4.9-4.B-75, compounds I.K-5.9-4.B-1 to I.K-5.9-4.B-75, compounds I.K-6.9-
4. B-1 to I.K-6.9-4.B-75, compounds I.K-7.9-4.B-1 to I.K-7.9-4.B-75, compounds I.K-8.9-4.B-1 to I.K-8.9-4.B-75).
Table 9-5 Compounds of the formula compounds I.L-1 , I.L-2, I.L-3, I.L-4J.L-5, I.L-6, I.L-7, I.L-8 in which the meaning for the combination of R7and R8for each individual compound corre- sponds in each case to one line of Table B (compounds I.L-1.9-5. B-1 to I.L-1.9-5. B-75, compounds I.L-2.9-5.B-1 to I.L-2.9-5. B-75, compounds I.L-3.9-5. B-1 to I.L-3.9-5.B-75, compounds I.L-4.9-5.B-1 to I.L-4.9-5.B-75, compounds I.L-5.9-5.B-1 to I.L-5.9-5.B-75, compounds I.L-6.9-
5. B-1 to I.L-6.9-5.B-75, compounds I.L-7.9-5.B-1 to I.L-7.9-5.B-75, compounds I.L-8.9-5.B-1 to I.L-8.9-5.B-75).
Table 9-6 Compounds of the formula compounds I.M-1, I.M-2, I.M-3, I.M-4,I.M-5, I.M-6, I.M-7, I.M-8 in which the meaning for the combination of R7and R8for each individual compound corresponds in each case to one line of Table B (compounds I.M-1.9-6. B-1 to I.M-1.9-6. B-75, compounds I.M-2.9-6. B-1 to I.M-2.9-6.B-75, compounds I.M-3.9-6. B-1 to I.M-3.9-6.B-75, compounds I.M-4.9-6.B-1 to I.M-4.9-6.B-75, compounds I.M-5.9-6.B-1 to I.M-5.9-6.B-75, com- pounds I.M-6.9-6. B-1 to I.M-6.9-6.B-75, compounds I.M-7.9-6.B-1 to I.M-7.9-6.B-75, compounds I.M-8.9-6.B-1 to I.M-8.9-6.B-75).
Table 9-7 Compounds of the formula compounds I.N-1, I.N-2, I.N-3, I.N-4J.N-5, I.N-6, I.N-7, I.N-8 in which the meaning for the combination of R7and R8for each individual compound corresponds in each case to one line of Table B (compounds I.N-1.9-7. B-1 to I.N-1.9-7. B-75, com- pounds I.N-2.9-7. B-1 to I.N-2.9-7. B-75, compounds I.N-3.9-7.B-1 to I.N-3.9-7.B-75, compounds I.N-4.9-7.B-1 to I.N-4.9-7.B-75, compounds I.N-5.9-7.B-1 to I.N-5.9-7.B-75, compounds I.N-6.9- 7.B-1 to I.N-6.9-7.B-75, compounds I.N-7.9-7.B-1 to I.N-7.9-7.B-75, compounds I.N-8.9-7.B-1 to I.N-8.9-7.B-75). Table B
The compounds I and the compositions according to the invention, respectively, are suitable as fungicides. They are distinguished by an outstanding effectiveness against a broad spectrum of phytopathogenic fungi, including soil-borne fungi, which derive especially from the classes of the Plasmodiophoromycetes, Peronosporomycetes (syn. Oomycetes), Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes (syn. Fungi imperfecti). Some are
systemically effective and they can be used in crop protection as foliar fungicides, fungicides for seed dressing and soil fungicides. Moreover, they are suitable for controlling harmful fungi, which inter alia occur in wood or roots of plants.
The compounds I and the compositions according to the invention are particularly important in the control of a multitude of phytopathogenic fungi on various cultivated plants, such as cereals, e. g. wheat, rye, barley, triticale, oats or rice; beet, e. g. sugar beet or fodder beet; fruits, such as pomes, stone fruits or soft fruits, e. g. apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, blackberries or gooseberries; leguminous plants, such as lentils, peas, alfalfa or soybeans; oil plants, such as rape, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palms, ground nuts or soybeans; cucurbits, such as squashes, cucumber or melons; fiber plants, such as cotton, flax, hemp or jute; citrus fruit, such as oranges, lemons, grapefruits or mandarins; vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, cucurbits or paprika; lauraceous plants, such as avocados, cinnamon or camphor; energy and raw material plants, such as corn, soybean, rape, sugar cane or oil palm; corn; tobacco; nuts; coffee; tea; bananas; vines (table grapes and grape juice grape vines); hop; turf; sweet leaf (also called Stevia); natural rubber plants or ornamental and forestry plants, such as flowers, shrubs, broad-leaved trees or evergreens, e. g. conifers; and on the plant propagation material, such as seeds, and the crop material of these plants.
Preferably, compounds I and compositions thereof, respectively are used for controlling a multitude of fungi on field crops, such as potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rape, legumes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.
The term "plant propagation material" is to be understood to denote all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e. g. pota- toes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants, including seedlings and young plants, which are to be transplanted after germination or after emergence from soil. These young plants may also be protected before transplantation by a total or partial treatment by immersion or pouring.
Preferably, treatment of plant propagation materials with compounds I and compositions thereof, respectively, is used for controlling a multitude of fungi on cereals, such as wheat, rye, barley and oats; rice, corn, cotton and soybeans.
The term "cultivated plants" is to be understood as including plants which have been modified by breeding, mutagenesis or genetic engineering including but not limiting to agricultural bi- otech products on the market or in development (cf. http://cera-gmc.org/, see GM crop database therein). Genetically modified plants are plants, which genetic material has been so modified by the use of recombinant DNA techniques that under natural circumstances cannot readily be obtained by cross breeding, mutations or natural recombination. Typically, one or more genes have been integrated into the genetic material of a genetically modified plant in order to improve certain properties of the plant. Such genetic modifications also include but are not limited to targeted post-translational modification of protein(s), oligo- or polypeptides e. g. by glycosylation or polymer additions such as prenylated, acetylated or farnesylated moieties or PEG moieties.
Plants that have been modified by breeding, mutagenesis or genetic engineering, e. g. have
been rendered tolerant to applications of specific classes of herbicides, such as auxin herbicides such as dicamba or 2,4-D; bleacher herbicides such as hydroxylphenylpyruvate dioxygen- ase (HPPD) inhibitors or phytoene desaturase (PDS) inhibitors; acetolactate synthase (ALS) inhibitors such as sulfonyl ureas or imidazolinones; enolpyruvylshikimate-3-phosphate synthase (EPSPS) inhibitors, such as glyphosate; glutamine synthetase (GS) inhibitors such as glufosinate; protoporphyrinogen-IX oxidase inhibitors; lipid biosynthesis inhibitors such as acetyl CoA carboxylase (ACCase) inhibitors; or oxynil (i. e. bromoxynil or ioxynil) herbicides as a result of conventional methods of breeding or genetic engineering. Furthermore, plants have been made resistant to multiple classes of herbicides through multiple genetic modifications, such as resistance to both glyphosate and glufosinate or to both glyphosate and a herbicide from another class such as ALS inhibitors, HPPD inhibitors, auxin herbicides, or ACCase inhibitors. These herbicide resistance technologies are e. g. described in Pest Managem. Sci. 61 , 2005, 246; 61 , 2005, 258; 61 , 2005, 277; 61 , 2005, 269; 61 , 2005, 286; 64, 2008, 326; 64, 2008, 332; Weed Sci. 57, 2009, 108; Austral. J. Agricult. Res. 58, 2007, 708; Science 316, 2007, 1 185; and references quoted therein. Several cultivated plants have been rendered tolerant to herbicides by conventional methods of breeding (mutagenesis), e. g. Clearfield® summer rape (Canola, BASF SE, Germany) being tolerant to imidazolinones, e. g. imazamox, or ExpressSun® sunflowers (DuPont, USA) being tolerant to sulfonyl ureas, e. g. tribenuron. Genetic engineering methods have been used to render cultivated plants such as soybean, cotton, corn, beets and rape, tolerant to herbicides such as glyphosate and glufosinate, some of which are commercially available under the trade names RoundupReady® (glyphosate-tolerant, Monsanto, U.S.A.), Cul- tivance® (imidazolinone tolerant, BASF SE, Germany) and LibertyLink® (glufosinate-tolerant, Bayer CropScience, Germany).
Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more insecticidal proteins, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as δ-endotoxins, e. g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl ) or Cry9c; vegetative insecticidal proteins (VIP), e. g. VIP1 , VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, e. g. Photorhabdus spp. or Xenorhabdus spp.; toxins produced by animals, such as scor- pion toxins, arachnid toxins, wasp toxins, or other insect-specific neurotoxins; toxins produced by fungi, such Streptomycetes toxins, plant lectins, such as pea or barley lectins; agglutinins; proteinase inhibitors, such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolism enzymes, such as 3-hydroxysteroid oxidase, ecdyster- oid-IDP-glycosyl-transferase, cholesterol oxidases, ecdysone inhibitors or HMG-CoA-reductase; ion channel blockers, such as blockers of sodium or calcium channels; juvenile hormone esterase; diuretic hormone receptors (helicokinin receptors); stilbene synthase, bibenzyl synthase, chitinases or glucanases. In the context of the present invention these insecticidal proteins or toxins are to be understood expressly also as pre-toxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by a new combination of protein domains, (see, e. g. WO 02/015701 ). Further examples of such toxins or genetically modified plants capable of synthesizing such toxins are disclosed, e. g., in EP-A 374 753, WO 93/007278,
WO 95/34656, EP-A 427 529, EP-A 451 878, WO 03/18810 und WO 03/52073. The methods for producing such genetically modified plants are generally known to the person skilled in the
art and are described, e. g. in the publications mentioned above. These insecticidal proteins contained in the genetically modified plants impart to the plants producing these proteins tolerance to harmful pests from all taxonomic groups of arthropods, especially to beetles (Coelop- tera), two-winged insects (Diptera), and moths (Lepidoptera) and to nematodes (Nematoda). Genetically modified plants capable to synthesize one or more insecticidal proteins are, e. g., described in the publications mentioned above, and some of which are commercially available such as YieldGard® (corn cultivars producing the CrylAb toxin), YieldGard® Plus (corn cultivars producing CrylAb and Cry3Bb1 toxins), Starlink® (corn cultivars producing the Cry9c toxin), Herculex® RW (corn cultivars producing Cry34Ab1 , Cry35Ab1 and the enzyme phosphinothri- cin-N-acetyltransferase [PAT]); NuCOTN® 33B (cotton cultivars producing the CrylAc toxin), Bollgard® I (cotton cultivars producing the CrylAc toxin), Bollgard® II (cotton cultivars producing CrylAc and Cry2Ab2 toxins); VIPCOT® (cotton cultivars producing a VIP-toxin); NewLeaf® (potato cultivars producing the Cry3A toxin); Bt-Xtra®, NatureGard®, KnockOut®, BiteGard®, Pro- tecta®, Bt1 1 (e. g. Agrisure® CB) and Bt176 from Syngenta Seeds SAS, France, (corn cultivars producing the CrylAb toxin and PAT enyzme), MIR604 from Syngenta Seeds SAS, France (corn cultivars producing a modified version of the Cry3A toxin, c.f. WO 03/018810), MON 863 from Monsanto Europe S.A., Belgium (corn cultivars producing the Cry3Bb1 toxin), IPC 531 from Monsanto Europe S.A., Belgium (cotton cultivars producing a modified version of the CrylAc toxin) and 1507 from Pioneer Overseas Corporation, Belgium (corn cultivars producing the Cry1 F toxin and PAT enzyme).
Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the resistance or tolerance of those plants to bacterial, viral or fungal pathogens. Examples of such proteins are the so-called "path- ogenesis-related proteins" (PR proteins, see, e. g. EP-A 392 225), plant disease resistance genes (e. g. potato cultivars, which express resistance genes acting against Phytophthora in- festans derived from the Mexican wild potato Solanum bulbocastanum) or T4-lysozym (e. g. potato cultivars capable of synthesizing these proteins with increased resistance against bacteria such as Erwinia amylvora). The methods for producing such genetically modified plants are generally known to the person skilled in the art and are described, e. g. in the publications men- tioned above.
Furthermore, plants are also covered that are by the use of recombinant DNA techniques capable to synthesize one or more proteins to increase the productivity (e. g. bio mass production, grain yield, starch content, oil content or protein content), tolerance to drought, salinity or other growth-limiting environmental factors or tolerance to pests and fungal, bacterial or viral pathogens of those plants.
Furthermore, plants are also covered that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve human or animal nutrition, e. g. oil crops that produce health-promoting long-chain omega-3 fatty acids or unsaturated omega-9 fatty acids (e. g. Nexera® rape, DOW Agro Sci- ences, Canada).
Furthermore, plants are also covered that contain by the use of recombinant DNA techniques a modified amount of substances of content or new substances of content, specifically to improve raw material production, e. g. potatoes that produce increased amounts of amylopectin (e. g. Amflora® potato, BASF SE, Germany).
The compounds I and compositions thereof, respectively, are particularly suitable for controlling the following plant diseases:
Albugo spp. (white rust) on ornamentals, vegetables (e. g. A. Candida) and sunflowers (e. g. A. tragopogonis); Altemaria spp. (Alternaria leaf spot) on vegetables, rape (A. brassicola or brassi- cae), sugar beets (A. tenuis), fruits, rice, soybeans, potatoes (e. g. A. solani or A. altemata), tomatoes (e. g. A. solani or A. altemata) and wheat; Aphanomyces spp. on sugar beets and vegetables; Ascochyta spp. on cereals and vegetables, e. g. A. tritici (anthracnose) on wheat and A. hordei on barley; Bipolaris and Drechslera spp. (teleomorph: Cochliobolus spp.), e. g. Southern leaf blight (D. maydis) or Northern leaf blight (B. zeicola) on corn, e. g. spot blotch (B. sorokin- iana) on cereals and e. g. B. oryzae on rice and turfs; Blumeria (formerly Erysiphe) graminis
(powdery mildew) on cereals (e. g. on wheat or barley); Botrytis cinerea (teleomorph: Botryotinia fuckeliana: grey mold) on fruits and berries (e. g. strawberries), vegetables (e. g. lettuce, carrots, celery and cabbages), rape, flowers, vines, forestry plants and wheat; Bremia lactucae (downy mildew) on lettuce; Ceratocystis (syn. Ophiostoma) spp. (rot or wilt) on broad-leaved trees and evergreens, e. g. C. ulmi (Dutch elm disease) on elms; Cercospora spp. (Cercospora leaf spots) on corn (e. g. Gray leaf spot: C. zeae-maydis), rice, sugar beets (e. g. C. beticola), sugar cane, vegetables, coffee, soybeans (e. g. C. sojina or C. kikuchii) and rice; Cladosporium spp. on tomatoes (e. g. C. fulvum: leaf mold) and cereals, e. g. C. herbarum (black ear) on wheat; Claviceps purpurea (ergot) on cereals; Cochliobolus (anamorph: Helminthosporium of Bipolaris) spp. (leaf spots) on corn (C. carbonum), cereals (e. g. C. sativus, anamorph: B. soro- kiniana) and rice (e. g. C. miyabeanus, anamorph: H. oryzae); Colletotrichum (teleomorph: Glo- merella) spp. (anthracnose) on cotton (e. g. C. gossypii), corn (e. g. C. graminicola: Anthracnose stalk rot), soft fruits, potatoes (e. g. C. coccodes: black dot), beans (e. g. C. lindemuthi- anum) and soybeans (e. g. C. truncatum or C. gloeosporioides); Corticium spp., e. g. C. sasakii (sheath blight) on rice; Corynespora cassiicola (leaf spots) on soybeans and ornamentals; Cy- cloconium spp., e. g. C. oleaginum on olive trees; Cylindrocarpon spp. (e. g. fruit tree canker or young vine decline, teleomorph: Nectria or Neonectria spp.) on fruit trees, vines (e. g. C. lirio- dendri, teleomorph: Neonectria liriodendri: Black Foot Disease) and ornamentals; Dematophora (teleomorph: Rosellinia) necatrix (root and stem rot) on soybeans; Diaporthe spp., e. g. D.
phaseolorum (damping off) on soybeans; Drechslera (syn. Helminthosporium, teleomorph: Pyr- enophora) spp. on corn, cereals, such as barley (e. g. D. teres, net blotch) and wheat (e. g. D. tritici-repentis: tan spot), rice and turf; Esca (dieback, apoplexy) on vines, caused by Formiti- poria (syn. Phellinus) punctata, F. mediterranea, Phaeomoniella chlamydospora (earlier Phaeo- acremonium chlamydosporum), Phaeoacremonium aleophilum and/or Botryosphaeria obtusa; Elsinoe spp. on pome fruits (£. pyri), soft fruits (£. veneta: anthracnose) and vines (£. ampelina: anthracnose); Entyloma oryzae (leaf smut) on rice; Epicoccum spp. (black mold) on wheat; Erysiphe spp. (powdery mildew) on sugar beets (£. betae), vegetables (e. g. E. pisi), such as cucurbits (e. g. E. cichoracearum), cabbages, rape (e. g. E. cruciferarum); Eutypa lata (Eutypa canker or dieback, anamorph: Cytosporina lata, syn. Libertella blepharis) on fruit trees, vines and ornamental woods; Exserohilum (syn. Helminthosporium) spp. on corn (e. g. E. turcicum); Fusarium (teleomorph: Gibberella) spp. (wilt, root or stem rot) on various plants, such as F. gra- minearum or F. culmorum (root rot, scab or head blight) on cereals (e. g. wheat or barley), F. oxysporum on tomatoes, F. solani (f. sp. glycines now syn. F. virguliforme ) and F. tucumaniae and F. brasiliense each causing sudden death syndrome on soybeans, and F. verticillioides on
corn; Gaeumannomyces graminis (take-all) on cereals (e. g. wheat or barley) and corn; Gibber- ella spp. on cereals (e. g. G. zeae) and rice (e. g. G. fujikuroi: Bakanae disease); Glomerella cingulata on vines, pome fruits and other plants and G. gossypii on cotton; Grainstaining complex on rice; Guignardia bidwellii (black rot) on vines; Gymnosporangium spp. on rosaceous plants and junipers, e. g. G. sabinae (rust) on pears; Helminthosporium spp. (syn. Drechslera, teleomorph: Cochliobolus) on corn, cereals and rice; Hemileia spp., e. g. H. vastatrix (coffee leaf rust) on coffee; Isariopsis clavispora (syn. Cladosporium vitis) on vines; Macrophomina phaseolina (syn. phaseoli) (root and stem rot) on soybeans and cotton; Microdochium (syn. Fusarium) nivale (pink snow mold) on cereals (e. g. wheat or barley); Microsphaera diffusa (powdery mildew) on soybeans; Monilinia spp., e. g. M. laxa, M. fructicola and M. fructigena (bloom and twig blight, brown rot) on stone fruits and other rosaceous plants; Mycosphaerella spp. on cereals, bananas, soft fruits and ground nuts, such as e. g. M. graminicola (anamorph: Septoria tritici, Septoria blotch) on wheat or M. fijiensis (black Sigatoka disease) on bananas; Peronospora spp. (downy mildew) on cabbage (e. g. P. brassicae), rape (e. g. P. parasitica), onions (e. g. P. destructor), tobacco (P. tabacina) and soybeans (e. g. P. manshurica);
Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans; Phialophora spp. e. g. on vines (e. g. P. tracheiphila and P. tetraspora) and soybeans (e. g. P. gregata: stem rot); Phoma lingam (root and stem rot) on rape and cabbage and P. betae (root rot, leaf spot and damping-off) on sugar beets; Phomopsis spp. on sunflowers, vines (e. g. P. viticola: can and leaf spot) and soybeans (e. g. stem rot: P. phaseoli, teleomorph: Diaporthe phaseolorum); Phy- soderma maydis (brown spots) on corn; Phytophthora spp. (wilt, root, leaf, fruit and stem root) on various plants, such as paprika and cucurbits (e. g. P. capsici), soybeans (e. g. P.
megasperma, syn. P. sojae), potatoes and tomatoes (e. g. P. infestans: late blight) and broad- leaved trees (e. g. P. ramorum: sudden oak death); Plasmodiophora brassicae (club root) on cabbage, rape, radish and other plants; Plasmopara spp., e. g. P. viticola (grapevine downy mildew) on vines and P. halstedii on sunflowers; Podosphaera spp. (powdery mildew) on rosaceous plants, hop, pome and soft fruits, e. g. P. leucotricha on apples; Polymyxa spp., e. g. on cereals, such as barley and wheat (P. graminis) and sugar beets (P. betae) and thereby transmitted viral diseases; Pseudocercosporella herpotrichoides (eyespot, teleomorph: Tapesia yal- lundae) on cereals, e. g. wheat or barley; Pseudoperonospora (downy mildew) on various plants, e. g. P. cubensis on cucurbits or P. humili on hop; Pseudopezicula tracheiphila (red fire disease or .rotbrenner', anamorph: Phialophora) on vines; Puccinia spp. (rusts) on various plants, e. g. P. triticina (brown or leaf rust), P. striiformis (stripe or yellow rust), P. hordei (dwarf rust), P. graminis (stem or black rust) or P. recondita (brown or leaf rust) on cereals, such as e. g. wheat, barley or rye, P. kuehnii (orange rust) on sugar cane and P. asparagi on asparagus; Pyrenophora (anamorph: Drechslera) tritici-repentis (tan spot) on wheat or P. feres (net blotch) on barley; Pyricularia spp., e. g. P. oryzae (teleomorph: Magnaporthe grisea, rice blast) on rice and P. grisea on turf and cereals; Pythium spp. (damping-off) on turf, rice, corn, wheat, cotton, rape, sunflowers, soybeans, sugar beets, vegetables and various other plants (e. g. P. ultimum or P. aphanidermatum); Ramularia spp., e. g. R. collo-cygni (Ramularia leaf spots, Physiological leaf spots) on barley and R. beticola on sugar beets; Rhizoctonia spp. on cotton, rice, potatoes, turf, corn, rape, potatoes, sugar beets, vegetables and various other plants, e. g. R. solani (root and stem rot) on soybeans, R. solani (sheath blight) on rice or R. cerealis (Rhizoctonia spring blight) on wheat or barley; Rhizopus stolonifer (black mold, soft rot) on strawberries, carrots,
cabbage, vines and tomatoes; Rhynchosporium secalis (scald) on barley, rye and triticale; Saro- cladium oryzae and S. attenuatum (sheath rot) on rice; Sclerotinia spp. (stem rot or white mold) on vegetables and field crops, such as rape, sunflowers (e. g. S. sclerotiorum) and soybeans (e. g. S. rolfsii or S. sclerotiorum); Septoria spp. on various plants, e. g. S. glycines (brown spot) on soybeans, S. tritici (Septoria blotch) on wheat and S. (syn. Stagonospora) nodorum
(Stagonospora blotch) on cereals; Uncinula (syn. Erysiphe) necator (powdery mildew, ana- morph: Oidium tuckeri) on vines; Setospaeria spp. (leaf blight) on corn (e. g. S. turcicum, syn. Helminthosporium turcicum) and turf; Sphacelotheca spp. (smut) on corn, (e. g. S. reiliana: head smut), sorghum und sugar cane; Sphaerotheca fuliginea (powdery mildew) on cucurbits; Spongospora subterranea (powdery scab) on potatoes and thereby transmitted viral diseases; Stagonospora spp. on cereals, e. g. S. nodorum (Stagonospora blotch, teleomorph: Lepto- sphaeria [syn. Phaeosphaeria] nodorum) on wheat; Synchytrium endobioticum on potatoes (potato wart disease); Taphrina spp., e. g. T. deformans (leaf curl disease) on peaches and T. pruni (plum pocket) on plums; Thielaviopsis spp. (black root rot) on tobacco, pome fruits, vegetables, soybeans and cotton, e. g. T. basicola (syn. Chalara elegans); Tilletia spp. (common bunt or stinking smut) on cereals, such as e. g. T. tritici (syn. T. caries, wheat bunt) and T. controversa (dwarf bunt) on wheat; Typhula incarnata (grey snow mold) on barley or wheat; Urocystis spp., e. g. U. occulta (stem smut) on rye; Uromyces spp. (rust) on vegetables, such as beans (e. g. U. appendiculatus, syn. U. phaseoli) and sugar beets (e. g. U. betae); Ustilago spp. (loose smut) on cereals (e. g. U. nuda and U. avaenae), corn (e. g. U. maydis: corn smut) and sugar cane; Venturia spp. (scab) on apples (e. g. V. inaequalis) and pears; and Verticillium spp. (wilt) on various plants, such as fruits and ornamentals, vines, soft fruits, vegetables and field crops, e. g. V. dahliae on strawberries, rape, potatoes and tomatoes.
The compounds I and compositions thereof, respectively, are also suitable for controlling harmful fungi in the protection of stored products or harvest and in the protection of materials.
The term "protection of materials" is to be understood to denote the protection of technical and non-living materials, such as adhesives, glues, wood, paper and paperboard, textiles, leather, paint dispersions, plastics, cooling lubricants, fiber or fabrics, against the infestation and destruction by harmful microorganisms, such as fungi and bacteria. As to the protection of wood and other materials, the particular attention is paid to the following harmful fungi: Ascomycetes such as Ophiostoma spp., Ceratocystis spp., Aureobasidium pullulans, Sclerophoma spp., Chaetomium spp., Humicola spp., Petriella spp., Trichurus spp.; Basidiomycetes such as Coni- ophora spp., Coriolus spp., Gloeophyllum spp., Lentinus spp., Pleurotus spp., Poria spp., Ser- pula spp. and Tyromyces spp., Deuteromycetes such as Aspergillus spp., Cladosporium spp., Penicillium spp., Trichoderma spp., Alternaria spp., Paecilomyces spp. and Zygomycetes such as Mucor spp., and in addition in the protection of stored products and harvest the following yeast fungi are worthy of note: Candida spp. and Saccharomyces cerevisae.
The method of treatment according to the invention can also be used in the field of protecting stored products or harvest against attack of fungi and microorganisms. According to the pre- sent invention, the term "stored products" is understood to denote natural substances of plant or animal origin and their processed forms, which have been taken from the natural life cycle and for which long-term protection is desired. Stored products of crop plant origin, such as plants or parts thereof, for example stalks, leafs, tubers, seeds, fruits or grains, can be protected in the freshly harvested state or in processed form, such as pre-dried, moistened, comminuted,
ground, pressed or roasted, which process is also known as post-harvest treatment. Also falling under the definition of stored products is timber, whether in the form of crude timber, such as construction timber, electricity pylons and barriers, or in the form of finished articles, such as furniture or objects made from wood. Stored products of animal origin are hides, leather, furs, hairs and the like. The combinations according the present invention can prevent disadvantageous effects such as decay, discoloration or mold. Preferably "stored products" is understood to denote natural substances of plant origin and their processed forms, more preferably fruits and their processed forms, such as pomes, stone fruits, soft fruits and citrus fruits and their processed forms.
The compounds I and compositions thereof, respectively, may be used for improving the health of a plant. The invention also relates to a method for improving plant health by treating a plant, its propagation material and/or the locus where the plant is growing or is to grow with an effective amount of compounds I and compositions thereof, respectively.
The term "plant health" is to be understood to denote a condition of the plant and/or its prod- ucts which is determined by several indicators alone or in combination with each other such as yield (e. g. increased biomass and/or increased content of valuable ingredients), plant vigor (e. g. improved plant growth and/or greener leaves ("greening effect")), quality (e. g. improved content or composition of certain ingredients) and tolerance to abiotic and/or biotic stress. The above identified indicators for the health condition of a plant may be interdependent or may re- suit from each other.
The compounds of formula I can be present in different crystal modifications whose biological activity may differ. They are likewise subject matter of the present invention.
The compounds I are employed as such or in form of compositions by treating the fungi or the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms to be protected from fungal attack with a fungicidally effective amount of the active substances. The application can be carried out both before and after the infection of the plants, plant propagation materials, such as seeds, soil, surfaces, materials or rooms by the fungi.
Plant propagation materials may be treated with compounds I as such or a composition comprising at least one compound I prophylactically either at or before planting or transplanting.
The invention also relates to agrochemical compositions comprising an auxiliary and at least one compound I according to the invention.
An agrochemical composition comprises a fungicidally effective amount of a compound I. The term "effective amount" denotes an amount of the composition or of the compounds I, which is sufficient for controlling harmful fungi on cultivated plants or in the protection of materi- als and which does not result in a substantial damage to the treated plants. Such an amount can vary in a broad range and is dependent on various factors, such as the fungal species to be controlled, the treated cultivated plant or material, the climatic conditions and the specific compound I used.
The compounds I, their N-oxides and salts can be converted into customary types of agro- chemical compositions, e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof. Examples for composition types are suspensions (e. g. SC, OD, FS), emulsifiable concentrates (e. g. EC), emulsions (e. g. EW, EO, ES, ME), capsules (e. g. CS, ZC), pastes, pastilles, wettable powders or dusts (e. g. WP, SP, WS, DP, DS), pressings (e. g. BR, TB, DT), granules (e. g. WG, SG, GR, FG, GG, MG), insecticidal
articles (e. g. LN), as well as gel formulations for the treatment of plant propagation materials such as seeds (e. g. GF). These and further compositions types are defined in the "Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 6th Ed. May 2008, CropLife International.
The compositions are prepared in a known manner, such as described by Mollet and Grube- mann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.
Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, disper- sants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimulants, compatibil- izers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifiers and binders.
Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e. g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin, tetrahydronaphthalene, alkyl- ated naphthalenes; alcohols, e. g. ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; glycols; DMSO; ketones, e. g. cyclohexanone; esters, e. g. lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e. g. N-methyl pyrrolidone, fatty acid dimethyl amides; and mixtures thereof.
Suitable solid carriers or fillers are mineral earths, e. g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, e. g. cellulose, starch; fertilizers, e. g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e. g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon's, Vol.1 : Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylaryl sulfonates, diphenyl sulfonates, alpha-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkyl naphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.
Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide. Exam-
pies of N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar- based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpoly- glucosides. Examples of polymeric surfactants are home- or copolymers of vinyl pyrrolidone, vi- nyl alcohols, or vinyl acetate.
Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetains and imidazolines. Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene ox- ide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of poly- acrylic acid or polyacid comb polymers. Examples of polybases are polyvinyl amines or polyethylene amines.
Suitable adjuvants are compounds, which have a negligible or even no pesticidal activity themselves, and which improve the biological performance of the compound I on the target. Examples are surfactants, mineral or vegetable oils, and other auxiliaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.
Suitable thickeners are polysaccharides (e. g. xanthan gum, carboxymethyl cellulose), inor- ganic clays (organically modified or unmodified), polycarboxylates, and silicates.
Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazoli- nones and benzisothiazolinones.
Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids. Suitable colorants (e. g. in red, blue, or green) are pigments of low water solubility and water-soluble dyes. Examples are inorganic colorants (e. g. iron oxide, titan oxide, iron hexacy- anoferrate) and organic colorants (e. g. alizarin-, azo- and phthalocyanine colorants).
Suitable tackifiers or binders are polyvinyl pyrrolidones, polyvinyl acetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, and cellulose ethers.
Examples for composition types and their preparation are:
i) Water-soluble concentrates (SL, LS)
10-60 wt% of a compound I and 5-15 wt% wetting agent (e. g. alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (e. g. alcohols) ad 100 wt%. The active sub- stance dissolves upon dilution with water.
ii) Dispersible concentrates (DC)
5-25 wt% of a compound I and 1 -10 wt% dispersant (e. g. polyvinyl pyrrolidone) are dissolved in organic solvent (e. g. cyclohexanone) ad 100 wt%. Dilution with water gives a dispersion.
iii) Emulsifiable concentrates (EC)
15-70 wt% of a compound I and 5-10 wt% emulsifiers (e. g. calcium dodecylbenzenesul- fonate and castor oil ethoxylate) are dissolved in water-insoluble organic solvent (e. g. aromatic hydrocarbon) ad 100 wt%. Dilution with water gives an emulsion,
iv) Emulsions (EW, EO, ES)
5-40 wt% of a compound I and 1 -10 wt% emulsifiers (e. g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40 wt% water-insoluble organic solvent (e. g. aromatic hydrocarbon). This mixture is introduced into water ad 100 wt% by means of an emulsifying machine and made into a homogeneous emulsion. Dilution with water gives an emulsion. v) Suspensions (SC, OD, FS)
In an agitated ball mill, 20-60 wt% of a compound I are comminuted with addition of 2-10 wt% dispersants and wetting agents (e. g. sodium lignosulfonate and alcohol ethoxylate), 0.1 - 2 wt% thickener (e. g. xanthan gum) and water ad 100 wt% to give a fine active substance suspension. Dilution with water gives a stable suspension of the active substance. For FS type composition up to 40 wt% binder (e. g. polyvinyl alcohol) is added.
vi) Water-dispersible granules and water-soluble granules (WG, SG)
50-80 wt% of a compound I are ground finely with addition of dispersants and wetting agents (e. g. sodium lignosulfonate and alcohol ethoxylate) ad 100 wt% and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.
vii) Water-dispersible powders and water-soluble powders (WP, SP, WS)
50-80 wt% of a compound I are ground in a rotor-stator mill with addition of 1 -5 wt% dispersants (e. g. sodium lignosulfonate), 1 -3 wt% wetting agents (e. g. alcohol ethoxylate) and solid carrier (e. g. silica gel) ad 100 wt%. Dilution with water gives a stable dispersion or solution of the active substance.
viii) Gel (GW, GF)
In an agitated ball mill, 5-25 wt% of a compound I are comminuted with addition of 3-10 wt% dispersants (e. g. sodium lignosulfonate), 1 -5 wt% thickener (e. g. carboxymethyl cellulose) and water ad 100 wt% to give a fine suspension of the active substance. Dilution with water gives a stable suspension of the active substance.
ix) Microemulsion (ME)
5-20 wt% of a compound I are added to 5-30 wt% organic solvent blend (e. g. fatty acid dimethyl amide and cyclohexanone), 10-25 wt% surfactant blend (e. g. alcohol ethoxylate and ar- ylphenol ethoxylate), and water ad 100 %. This mixture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion.
x) Microcapsules (CS)
An oil phase comprising 5-50 wt% of a compound I, 0-40 wt% water insoluble organic solvent (e. g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e. g. methylmethacrylate, methacrylic acid and a di- or triacrylate) are dispersed into an aqueous solution of a protective colloid (e. g. polyvinyl alcohol). Radical polymerization results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase comprising 5-50 wt% of a compound I according to the invention, 0-40 wt% water insoluble organic solvent (e. g. aromatic hydrocarbon), and an isocya- nate monomer (e. g. diphenylmethene-4,4'-diisocyanatae) are dispersed into an aqueous solu- tion of a protective colloid (e. g. polyvinyl alcohol). The addition of a polyamine (e. g. hexameth- ylenediamine) results in the formation of polyurea microcapsules. The monomers amount to 1 - 10 wt%. The wt% relate to the total CS composition.
xi) Dustable powders (DP, DS)
1 -10 wt% of a compound I are ground finely and mixed intimately with solid carrier (e. g.
finely divided kaolin) ad 100 wt%.
xii) Granules (GR, FG)
0.5-30 wt% of a compound I is ground finely and associated with solid carrier (e. g. silicate) ad 100 wt%. Granulation is achieved by extrusion, spray-drying or fluidized bed.
xiii) Ultra-low volume liquids (UL)
1 -50 wt% of a compound I are dissolved in organic solvent (e. g. aromatic hydrocarbon) ad 100 wt%.
The compositions types i) to xiii) may optionally comprise further auxiliaries, such as 0.1 -1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1 -1 wt% anti-foaming agents, and 0.1 -1 wt% colorants.
The agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, more preferably between 1 and 70%, and in particular between 10 and 60%, by weight of active substance. The active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
For the purposes of treatment of plant propagation materials, particularly seeds, solutions for seed treatment (LS), Suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC), and gels (GF) are usually employed. The com- positions in question give, after two-to-tenfold dilution, active substance concentrations of from 0.01 to 60% by weight, preferably from 0.1 to 40%, in the ready-to-use preparations. Application can be carried out before or during sowing. Methods for applying compound I and compositions thereof, respectively, onto plant propagation material, especially seeds, include dressing, coating, pelleting, dusting, and soaking as well as in-furrow application methods. Preferably, com- pound I or the compositions thereof, respectively, are applied on to the plant propagation material by a method such that germination is not induced, e. g. by seed dressing, pelleting, coating and dusting.
When employed in plant protection, the amounts of active substances applied are, depend- ing on the kind of effect desired, from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 0.9 kg per ha, and in particular from 0.1 to 0.75 kg per ha.
In treatment of plant propagation materials such as seeds, e. g. by dusting, coating or drenching seed, amounts of active substance of from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g, per 100 kilogram of plant propagation material (preferably seeds) are generally required.
When used in the protection of materials or stored products, the amount of active substance applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material.
Various types of oils, wetters, adjuvants, fertilizer, or micronutrients, and further pesticides (e. g. herbicides, insecticides, fungicides, growth regulators, safeners, biopesticides) may be added to the active substances or the compositions comprising them as premix or, if appropriate not until immediately prior to use (tank mix). These agents can be admixed with the compositions according to the invention in a weight ratio of 1 :100 to 100:1 , preferably 1 :10 to 10:1.
A pesticide is generally a chemical or biological agent (such as pestidal active ingredient, compound, composition, virus, bacterium, antimicrobial or disinfectant) that through its effect deters, incapacitates, kills or otherwise discourages pests. Target pests can include insects, plant pathogens, weeds, mollusks, birds, mammals, fish, nematodes (roundworms), and mi- crobes that destroy property, cause nuisance, spread disease or are vectors for disease. The term "pesticide" includes also plant growth regulators that alter the expected growth, flowering, or reproduction rate of plants; defoliants that cause leaves or other foliage to drop from a plant, usually to facilitate harvest; desiccants that promote drying of living tissues, such as unwanted plant tops; plant activators that activate plant physiology for defense of against certain pests; safeners that reduce unwanted herbicidal action of pesticides on crop plants; and plant growth promoters that affect plant physiology e.g. to increase plant growth, biomass, yield or any other quality parameter of the harvestable goods of a crop plant.
Biopesticides have been defined as a form of pesticides based on microorganisms (bacteria, fungi, viruses, nematodes, etc.) or natural products (compounds, such as metabolites, proteins, or extracts from biological or other natural sources) (U.S. Environmental Protection Agency: http://www.epa.gov/pesticides/biopesticides/). Biopesticides fall into two major classes, microbial and biochemical pesticides:
(1 ) Microbial pesticides consist of bacteria, fungi or viruses (and often include the metabolites that bacteria and fungi produce). Entomopathogenic nematodes are also classified as microbial pesticides, even though they are multi-cellular.
(2) Biochemical pesticides are naturally occurring substances that control pests or provide other crop protection uses as defined below, but are relatively non-toxic to mammals.
The user applies the composition according to the invention usually from a predosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the agro- chemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained. Usually, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.
According to one embodiment, individual components of the composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank or any other kind of vessel used for applications (e. g. seed treater drums, seed pelleting machinery, knapsack sprayer) and further auxiliaries may be added, if appropriate.
When living microorganisms, such as microbial pesticides from groups L1 ), L3) and L5), form part of such kit, it must be taken care that choice and amounts of the components (e. g. chemical pesticides) and of the further auxiliaries should not influence the viability of the microbial pesticides in the composition mixed by the user. Especially for bactericides and solvents, compatibility with the respective microbial pesticide has to be taken into account.
Consequently, one embodiment of the invention is a kit for preparing a usable pesticidal composition, the kit comprising a) a composition comprising component 1 ) as defined herein and at least one auxiliary; and b) a composition comprising component 2) as defined herein and at least one auxiliary; and optionally c) a composition comprising at least one auxiliary and optionally a further active component 3) as defined herein.
Mixing the compounds I or the compositions comprising them in the use form as fungicides
with other fungicides results in many cases in an expansion of the fungicidal spectrum of activity being obtained or in a prevention of fungicide resistance development. Furthermore, in many cases, synergistic effects are obtained.
The following list of pesticides II (e. g. pesticidally-active substances and biopesticides), in conjunction with which the compounds I can be used, is intended to illustrate the possible combinations but does not limit them:
A) Respiration inhibitors
Inhibitors of complex III at Q0 site: azoxystrobin (A.1 .1 ), coumethoxystrobin (A.1 .2), coumoxystrobin (A.1.3), dimoxystrobin (A.1 .4), enestroburin (A.1.5), fenaminstrobin (A.1 .6), fenoxystrobin/flufenoxystrobin (A.1 .7), fluoxastrobin (A.1 .8), kresoxim-methyl (A.1.9), man- destrobin (A.1 .10), metominostrobin (A.1.1 1 ), orysastrobin (A.1 .12), picoxystrobin (A.1.13), pyraclostrobin (A.1.14), pyrametostrobin (A.1 .15), pyraoxystrobin (A.1.16), trifloxystrobin (A.1.17), 2-(2-(3-(2,6-dichlorophenyl)-1 -methyl-allylideneaminooxymethyl)-phenyl)-2-meth- oxyimino-N-methyl-acetamide (A.1.18), pyribencarb (A.1 .19), triclopyricarb/chlorodincarb (A.1.20), famoxadone (A.1 .21 ), fenamidone (A.1 .21 ), methyl-A/-[2-[(1 ,4-dimethyl-5-phenyl- pyrazol-3-yl)oxylmethyl]phenyl]-N-methoxy-carbamate (A.1.22), 1 -[3-chloro-2-[[1 -(4-chloro- phenyl)-1 H-pyrazol-3-yl]oxymethyl]phenyl]-4-methyl-tetrazol-5-one (A.1.23), 1 -[3-bromo-2- [[1 -(4-chlorophenyl)pyrazol-3-yl]oxymethyl]phenyl]-4-methyl-tetrazol-5-one (A.1.24), 1 -[2-[[1 - (4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one (A.1.25), 1 -[2-[[1 -(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-fluoro-phenyl]-4-methyl-tetrazol-5-one
(A.1.26), 1 -[2-[[1 -(2,4-dichlorophenyl)pyrazol-3-yl]oxymethyl]-3-fluoro-phenyl]-4-methyl-te- trazol-5-one (A.1 .27), 1 -[3-cyclopropyl-2-[[2-methyl-4-(1 -methylpyrazol-3-yl)phenoxy]me- thyl]phenyl]-4-methyl-tetrazol-5-one (A.1 .30), 1 -[3-(difluoromethoxy)-2-[[2-methyl-4- (1 -methylpyrazol-3-yl)phenoxy]methyl]phenyl]-4-methyl-tetrazol-5-one (A.1 .31 ), 1 -methyl-4- [3-rnethyl-2-[[2-methyl-4-(1 -methylpyrazol-3-yl)phenoxy]methyl]phenyl]tetrazol-5-one
(A.1.32), (Z,2E)-5-[1 -(2,4-dichlorophenyl)pyrazol-3-yl]-oxy-2-methoxyimino-/V,3-dimethyl- pent-3-enamide (A.1 .34), (Z,2£)-5-[1 -(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-A/,3- dimethyl-pent-3-enamide (A.1.35), pyriminostrobin (A.1.36), bifujunzhi (A.1 .37), 2-(ortho- ((2,5-dimethylphenyl-oxymethylen)phenyl)-3-methoxy-acrylic acid methylester (A.1.38); - inhibitors of complex III at Q, site: cyazofamid (A.2.1 ), amisulbrom (A.2.2),
[(6SJR,8R)-8-benzyl-3-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-di- oxo-1 ,5-dioxonan-7-yl] 2-methylpropanoate (A.2.3), fenpicoxamid (A.2.4);
- inhibitors of complex II: benodanil (A.3.1 ), benzovindiflupyr (A.3.2), bixafen (A.3.3), boscalid (A.3.4), carboxin (A.3.5), fenfuram (A.3.6), fluopyram (A.3.7), flutolanil (A.3.8), fluxapyroxad (A.3.9), furametpyr (A.3.10), isofetamid (A.3.1 1 ), isopyrazam (A.3.12), mepronil (A.3.13), ox- ycarboxin (A.3.14), penflufen (A.3.15), penthiopyrad (A.3.16), pydiflumetofen (A.3.17), pyra- ziflumid (A.3.18), sedaxane (A.3.19), tecloftalam (A.3.20), thifluzamide (A.3.21 ), 3-(difluoro- methyl)-1 -methyl-N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide (A.3.22), 3-(trifluoro- methyl)-1 -methyl-N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide (A.3.23), 1 ,3-dime- thyl-N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide (A.3.24), 3-(trifluoromethyl)-1 ,5-di- methyl-N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide (A.3.25), 1 ,3,5-trimethyl-N- (1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide (A.3.26), 3-(difluoromethyl)-1 ,5-dimethyl- N-(1 ,1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide (A.3.27), 3-(difluoromethyl)-N-(7-fluoro-
1 ,1 ,3-trimethyl-indan-4-yl)-1 -methyl-pyrazole-4-carboxamide (A.3.28), N-[(5-chloro-2-isopro- pyl-phenyl)methyl]-N-cyclopropyl-5-fluoro-1 ,3-dimethyl-pyrazole-4-carboxamide (A.3.29), methyl (E)-2-[2-[(5-cyano-2-methyl-phenoxy)methyl]phenyl]-3-methoxy-prop-2-enoate (A.3.30), N-[(5-chloro-2-isopropyl-phenyl)methyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1 - methyl-pyrazole-4-carboxamide (A.3.31 ), 2-(difluoromethyl)-N-(1 ,1 ,3-trimethyl-indan-4-yl)pyr- idine-3-carboxamide (A.3.32), 2-(difluoromethyl)-N-[(3R)-1 ,1 ,3-trimethylindan-4-yl]pyridine-3- carboxamide (A.3.33), 2-(difluoromethyl)-N-(3-ethyl-1 ,1 -dimethyl-indan-4-yl)pyridine-3-car- boxamide (A.3.34), 2-(difluoromethyl)-N-[(3R)-3-ethyl-1 ,1 -dimethyl-indan-4-yl]pyridine-3-car- boxamide (A.3.35), 2-(difluoromethyl)-N-(1 ,1 -dimethyl-3-propyl-indan-4-yl)pyridine-3-carbox- amide (A.3.36), 2-(difluoromethyl)-N-[(3R)-1 ,1 -dimethyl-3-propyl-indan-4-yl]pyridine-3-car- boxamide (A.3.37), 2-(difluoromethyl)-N-(3-isobutyl-1 ,1 -dimethyl-indan-4-yl)pyridine-3-car- boxamide (A.3.38), 2-(difluoromethyl)-N-[(3R)-3-isobutyl-1 ,1 -dimethyl-indan-4-yl]pyridine-3- carboxamide (A.3.39);
- other respiration inhibitors: diflumetorim (A.4.1 ); nitrophenyl derivates: binapacryl (A.4.2), di- nobuton (A.4.3), dinocap (A.4.4), fluazinam (A.4.5), meptyldinocap (A.4.6), ferimzone
(A.4.7); organometal compounds: fentin salts, e. g. fentin-acetate (A.4.8), fentin chloride (A.4.9) or fentin hydroxide (A.4.10); ametoctradin (A.4.1 1 ); silthiofam (A.4.12);
B) Sterol biosynthesis inhibitors (SBI fungicides)
- C14 demethylase inhibitors: triazoles: azaconazole (B.1.1 ), bitertanol (B.1.2), bromucona- zole (B.1 .3), cyproconazole (B.1 .4), difenoconazole (B.1 .5), diniconazole (B.1 .6), dinicona- zole-M (B.1.7), epoxiconazole (B.1 .8), fenbuconazole (B.1 .9), fluquinconazole (B.1 .10), flusi- lazole (B.1 .1 1 ), flutriafol (B.1.12), hexaconazole (B.1.13), imibenconazole (B.1.14), ipcona- zole (B.1 .15), metconazole (B.1.17), myclobutanil (B.1.18), oxpoconazole (B.1 .19), paclobu- trazole (B.1.20), penconazole (B.1.21 ), propiconazole (B.1 .22), prothioconazole (B.1.23), simeconazole (B.1.24), tebuconazole (B.1.25), tetraconazole (B.1.26), triadimefon (B.1.27), triadimenol (B.1.28), triticonazole (B.1 .29), uniconazole (B.1.30), ipfentrifluconazole, (B.1 .37), mefentrifluconazole (B.1.38), 2-(chloromethyl)-2-methyl-5-(p-tolylmethyl)-1 -(1 ,2,4- triazol-1 -ylmethyl)cyclopentanol (B.1.43); imidazoles: imazalil (B.1.44), pefurazoate (B.1.45), prochloraz (B.1.46), triflumizol (B.1 .47); pyrimidines, pyridines and piperazines: fenarimol (B.1.49), pyrifenox (B.1 .50), triforine (B.1 .51 ), [3-(4-chloro-2-fluoro-phenyl)-5-(2,4-difluoro- phenyl)isoxazol-4-yl]-(3-pyridyl)methanol (B.1 .52);
- Delta14-reductase inhibitors: aldimorph (B.2.1 ), dodemorph (B.2.2), dodemorph-acetate (B.2.3), fenpropimorph (B.2.4), tridemorph (B.2.5), fenpropidin (B.2.6), piperalin (B.2.7), spi- roxamine (B.2.8);
- Inhibitors of 3-keto reductase: fenhexamid (B.3.1 );
- Other Sterol biosynthesis inhibitors: chlorphenomizole (B.4.1 );
C) Nucleic acid synthesis inhibitors
- phenylamides or acyl amino acid fungicides: benalaxyl (C.1.1 ), benalaxyl-M (C.1 .2), kiralaxyl (C.1 .3), metalaxyl (C.1.4), metalaxyl-M (C.1 .5), ofurace (C.1 .6), oxadixyl (C.1 .7);
- other nucleic acid synthesis inhibitors: hymexazole (C.2.1 ), octhilinone (C.2.2), oxolinic acid (C.2.3), bupirimate (C.2.4), 5-fluorocytosine (C.2.5), 5-fluoro-2-(p-tolylmethoxy)pyrimidin- 4-amine (C.2.6), 5-fluoro-2-(4-fluorophenylmethoxy)pyrimidin-4-amine (C.2.7), 5-fluoro- 2-(4-chlorophenylmethoxy)pyrimidin-4 amine (C.2.8);
D) Inhibitors of cell division and cytoskeleton
- tubulin inhibitors: benomyl (D.1.1 ), carbendazim (D.1.2), fuberidazole (D1.3), thiabendazole (D.1 .4), thiophanate-methyl (D.1.5), 3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyri- dazine (D.1.6), 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine (D.1 .7), N-eth- yl-2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]butanamide (D.1.8), N-ethyl-2-[(3-ethynyl-8-methyl- 6-quinolyl)oxy]-2-methylsulfanyl-acetamide (D.1.9), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]- N-(2-fluoroethyl)butanamide (D.1.10), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroeth- yl)-2-methoxy-acetamide (D.1 .1 1 ), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-propyl-butanam- ide (D.1 .12), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methoxy-N-propyl-acetamide (D.1.13), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methylsulfanyl-N-propyl-acetamide (D.1.14), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)-2-methylsulfanyl-acetamide (D.1 .15), 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine (D.1 .16);
- other cell division inhibitors: diethofencarb (D.2.1 ), ethaboxam (D.2.2), pencycuron (D.2.3), fluopicolide (D.2.4), zoxamide (D.2.5), metrafenone (D.2.6), pyriofenone (D.2.7);
E) Inhibitors of amino acid and protein synthesis
- methionine synthesis inhibitors: cyprodinil (E.1 .1 ), mepanipyrim (E.1 .2), pyrimethanil (E.1.3);
- protein synthesis inhibitors: blasticidin-S (E.2.1 ), kasugamycin (E.2.2), kasugamycin hydro- chloride-hydrate (E.2.3), mildiomycin (E.2.4), streptomycin (E.2.5), oxytetracyclin (E.2.6);
F) Signal transduction inhibitors
- MAP / histidine kinase inhibitors: fluoroimid (F.1 .1 ), iprodione (F.1 .2), procymidone (F.1 .3), vinclozolin (F.1 .4), fludioxonil (F.1.5);
- G protein inhibitors: quinoxyfen (F.2.1 );
G) Lipid and membrane synthesis inhibitors
- Phospholipid biosynthesis inhibitors: edifenphos (G.1.1 ), iprobenfos (G.1 .2), pyrazophos (G.1.3), isoprothiolane (G.1 .4);
- lipid peroxidation: dicloran (G.2.1 ), quintozene (G.2.2), tecnazene (G.2.3), tolclofos-methyl (G.2.4), biphenyl (G.2.5), chloroneb (G.2.6), etridiazole (G.2.7);
- phospholipid biosynthesis and cell wall deposition: dimethomorph (G.3.1 ), flumorph (G.3.2), mandipropamid (G.3.3), pyrimorph (G.3.4), benthiavalicarb (G.3.5), iprovalicarb (G.3.6), valifenalate (G.3.7);
- compounds affecting cell membrane permeability and fatty acides: propamocarb (G.4.1 );
- inhibitors of oxysterol binding protein: oxathiapiprolin (G.5.1 ), 2-{3-[2-(1 -{[3,5-bis(difluorome- thyl-1 H-pyrazol-1 -yl]acetyl}piperidin-4-yl)-1 ,3-thiazol-4-yl]-4,5-dihydro-1 ,2-oxazol-5-yl}phenyl methanesulfonate (G.5.2), 2-{3-[2-(1 -{[3,5-bis(difluoromethyl)-1 H-pyrazol-1 -yl]acetyl}piperi- din-4-yl) 1 ,3-thiazol-4-yl]-4,5-dihydro-1 ,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate
(G.5.3), 4-[1 -[2-[3-(difluoromethyl)-5-methyl-pyrazol-1 -yl]acetyl]-4-piperidyl]-N-tetralin-1 -yl- pyridine-2-carboxamide (G.5.4), 4-[1 -[2-[3,5-bis(difluoromethyl)pyrazol-1 -yl]acetyl]-4-pi- peridyl]-N-tetralin-1 -yl-pyridine-2-carboxamide (G.5.5), 4-[1 -[2-[3-(difluoromethyl)-5-(trifluoro- methyl)pyrazol-1 -yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.6), 4-[1 - [2-[5-cyclopropyl-3-(difluoromethyl)pyrazol-1 -yl]acetyl]-4-piperidyl]-N-tetralin-1 -yl-pyridine-2- carboxamide (G.5.7), 4-[1 -[2-[5-methyl-3-(trifluoromethyl)pyrazol-1 -yl]acetyl]-4-piperidyl]-N- tetralin-1 -yl-pyridine-2-carboxamide (G.5.8), 4-[1 -[2-[5-(difluoromethyl)-3-(trifluoromethyl)py- razol-1 -yl]acetyl]-4-piperidyl]-N-tetralin-1 -yl-pyridine-2-carboxamide (G.5.9), 4-[1 -[2-[3,5- bis(trifluoromethyl)pyrazol-1 -yl]acetyl]-4-piperidyl]-N-tetralin-1 -yl-pyridine-2-carboxamide
(G.5.10), (4-[1 -[2-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1 -yl]acetyl]-4-piperidyl]-N-tetralin- 1 -yl-pyridine-2-carboxamide (G.5.1 1 );
H) Inhibitors with Multi Site Action
- inorganic active substances: Bordeaux mixture (H.1.1 ), copper (H.1 .2), copper acetate
(H.1 .3), copper hydroxide (H.1 .4), copper oxychloride (H.1 .5), basic copper sulfate (H.1 .6), sulfur (H.1.7);
- thio- and dithiocarbamates: ferbam (H.2.1 ), mancozeb (H.2.2), maneb (H.2.3), metam
(H.2.4), metiram (H.2.5), propineb (H.2.6), thiram (H.2.7), zineb (H.2.8), ziram (H.2.9);
- organochlorine compounds: anilazine (H.3.1 ), chlorothalonil (H.3.2), captafol (H.3.3), captan (H.3.4), folpet (H.3.5), dichlofluanid (H.3.6), dichlorophen (H.3.7), hexachlorobenzene
(H.3.8), pentachlorphenole (H.3.9) and its salts, phthalide (H.3.10), tolylfluanid (H.3.1 1 );
- guanidines and others: guanidine (H.4.1 ), dodine (H.4.2), dodine free base (H.4.3),
guazatine (H.4.4), guazatine-acetate (H.4.5), iminoctadine (H.4.6), iminoctadine-triacetate (H.4.7), iminoctadine-tris(albesilate) (H.4.8), dithianon (H.4.9), 2,6-dimethyl-1 H,5H- [1 ,4]dithiino[2,3-c:5,6-c']dipyrrole-1 ,3,5,7(2H,6H)-tetraone (H.4.10);
I) Cell wall synthesis inhibitors
- inhibitors of glucan synthesis: validamycin (1.1.1 ), polyoxin B (1.1 .2);
- melanin synthesis inhibitors: pyroquilon (1.2.1 ), tricyclazole (1.2.2), carpropamid (1.2.3), dicy- clomet (I.2.4), fenoxanil (I.2.5);
J) Plant defence inducers
- acibenzolar-S-methyl (J.1.1 ), probenazole (J.1 .2), isotianil (J.1 .3), tiadinil (J.1 .4), prohexadi- one-calcium (J.1 .5); phosphonates: fosetyl (J.1 .6), fosetyl-aluminum (J.1 .7), phosphorous acid and its salts (J.1 .8), calcium phosphonate (J.1 .1 1 ), potassium phosphonate (J.1.12), potassium or sodium bicarbonate (J.1.9), 4-cyclopropyl-N-(2,4-dimethoxyphenyl)thiadiazole- 5-carboxamide (J.1 .10);
K) Unknown mode of action
- bronopol (K.1.1 ), chinomethionat (K.1 .2), cyflufenamid (K.1 .3), cymoxanil (K.1.4), dazomet (K.1.5), debacarb (K.1.6), diclocymet (K.1.7), diclomezine (K.1 .8), difenzoquat (K.1.9), difen- zoquat-methylsulfate (K.1 .10), diphenylamin (K.1 .1 1 ), fenitropan (K.1 .12), fenpyrazamine (K.1.13), flumetover (K.1 .14), flusulfamide (K.1 .15), flutianil (K.1 .16), harpin (K.1 .17), metha- sulfocarb (K.1.18), nitrapyrin (K.1.19), nitrothal-isopropyl (K.1.20), tolprocarb (K.1.21 ), oxin- copper (K.1 .22), proquinazid (K.1.23), tebufloquin (K.1 .24), tecloftalam (K.1.25), triazoxide (K.1.26), N'-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl formamidine (K.1.27), N'-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-eth- yl-N-methyl formamidine (K.1 .28), N'-[4-[[3-[(4-chlorophenyl)methyl]-1 ,2,4-thiadiazol-5-yl]- oxy]-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine (K.1 .29), N'-(5-bromo-6-indan-2- yloxy-2-methyl-3-pyridyl)-N-ethyl-N-methyl-formamidine (K.1 .30), N'-[5-bromo-6-[1 -(3,5-diflu- orophenyl)ethoxy]-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.31 ), N'-[5-bromo- 6-(4-isopropylcyclohexoxy)-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.32), N'-[5-bromo-2-methyl-6-(1 -phenylethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.33), N'-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methyl formamidine (K.1.34), N'-(5-difluoromethyl-2-methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl- N-methyl formamidine (K.1.35), 2-(4-chloro-phenyl)-N-[4-(3,4-dimethoxy-phenyl)-isoxazol- 5-yl]-2-prop-2-ynyloxy-acetamide (K.1.36), 3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin-
3-yl]-pyridine (pyrisoxazole) (K.1 .37), 3-[5-(4-methylphenyl)-2,3-dimethyl-isoxazolidin-3 yl]- pyridine (K.1 .38), 5-chloro-1 -(4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1 H-benzoimidazole (K.1.39), ethyl (Z)-3-amino-2-cyano-3-phenyl-prop-2-enoate (K.1.40), picarbutrazox (K.1.41 ), pentyl N-[6-[[(Z)-[(1 -methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carba- mate (K.1.42), but-3-ynyl N-[6-[[(Z)-[(1 -methyltetrazol-5-yl)-phenyl-methylene]amino]oxyme- thyl]-2-pyridyl]carbamate (K.1 .43), 2-[2-[(7,8-difluoro-2-methyl-3-quinolyl)oxy]-6-fluoro-phe- nyl]propan-2-ol (K.1 .44), 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phen-yl]propan-2-ol (K.1.45), quinofumelin (K.1 .47), 9-fluoro-2,2-dimethyl-5-(3-quinolyl)-3H-1 ,4-benzoxazepine (K.1.49), 2-(6-benzyl-2-pyridyl)quinazoline (K.1 .50), 2-[6-(3-fluoro-4-methoxy-phenyl)-5-me- thyl-2-pyridyl]quinazoline (K.1 .51 ), dichlobentiazox (K.1 .52), N'-(2,5-dimethyl-4-phenoxy- phenyl)-N-ethyl-N-methyl-formamidine (K.1 .53);
Biopesticides
L1 ) Microbial pesticides with fungicidal, bactericidal, viricidal and/or plant defense activator activity: Ampelomyces quisqualis, Aspergillus flavus, Aureobasidium pullulans, Bacillus altitudinis, B. amyloliquefaciens, B. megaterium, B. mojavensis, B. mycoides, B. pu- milus, B. simplex, B. solisalsi, B. subtilis, B. subtilis var. amyloliquefaciens, Candida oleophila, C. saitoana, Clavibacter michiganensis (bacteriophages), Coniothyrium mini- tans, Cryphonectria parasitica, Cryptococcus albidus, Dilophosphora alopecuri, Fusarium oxysporum, Clonostachys rosea f. catenulate (also named Gliocladium ca- tenulatum), Gliocladium roseum, Lysobacter antibioticus, L. enzymogenes, Metschni- kowia fructicola, Microdochium dimerum, Microsphaeropsis ochracea, Muscodor albus, Paenibacillus alvei, Paenibacillus polymyxa, Pantoea vagans, Penicillium bilaiae, Phle- biopsis gigantea, Pseudomonas sp., Pseudomonas chloraphis, Pseudozyma floccu- losa, Pichia anomala, Pythium oligandrum, Sphaerodes mycoparasitica, Streptomyces griseoviridis, S. lydicus, S. violaceusniger, Talaromyces flavus, Trichoderma asperel- loides, T. asperellum, T. atroviride, T. fertile, T. gamsii, T. harmatum, T. harzianum, T. polysporum, T. stromaticum, T. virens, T. viride, Typhula phacorrhiza, Ulocladium oudemansii, Verticillium dahlia, zucchini yellow mosaic virus (avirulent strain);
L2) Biochemical pesticides with fungicidal, bactericidal, viricidal and/or plant defense activator activity: harpin protein, Reynoutria sachalinensis extract;
L3) Microbial pesticides with insecticidal, acaricidal, molluscidal and/or nematicidal activity:
Agrobacterium radiobacter, Bacillus cereus, B. firmus, B. thuringiensis, B. thuringiensis ssp. aizawai, B. t. ssp. israelensis, B. t. ssp. galleriae, B. t. ssp. kurstaki, B. t. ssp. fe- nebrionis, Beauveria bassiana, B. brongniartii, Burkholderia spp., Chromobacterium subtsugae, Cydia pomonella granulovirus (CpGV), Cryptophlebia leucotreta granulovi- rus (CrleGV), Flavobacterium spp., Helicoverpa armigera nucleopolyhedrovirus (HearNPV), Helicoverpa zea nucleopolyhedrovirus (HzNPV), Helicoverpa zea single capsid nucleopolyhedrovirus (HzSNPV), Heterorhabditis bacteriophora, Isaria fumoso- rosea, Lecanicillium longisporum, L. muscarium, Metarhizium anisopliae, Metarhizium anisopliae var. anisopliae, M. anisopliae var. acridum, Nomuraea rileyi, Paecilomyces fumosoroseus, P. lilacinus, Paenibacillus popilliae, Pasteuria spp., P. nishizawae, P. penetrans, P. ramosa, P. thornea, P. usgae, Pseudomonas fluorescens, Spodoptera littoralis nucleopolyhedrovirus (SpliNPV), Steinernema carpocapsae, S. feltiae, S. kraussei, Streptomyces galbus, S. microflavus;
L4) Biochemical pesticides with insecticidal, acaricidal, molluscidal, pheromone and/or ne- maticidal activity: L-carvone, citral, (E,Z)-7,9-dodecadien-1 -yl acetate, ethyl formate, (E,Z)-2,4-ethyl decadienoate (pear ester), (Z,Z,E)-7,1 1 ,13-hexadecatrienal, heptyl bu- tyrate, isopropyl myristate, lavanulyl senecioate, cis-jasmone, 2-methyl 1 -butanol, methyl eugenol, methyl jasmonate, (E,Z)-2,13-octadecadien-1 -ol, (E,Z)-2,13-octadeca- dien-1 -ol acetate, (E,Z)-3,13-octadecadien-1 -ol, R-1 -octen-3-ol, pentatermanone, (E,Z,Z)-3,8,1 1 -tetradecatrienyl acetate, (Z,E)-9,12-tetradecadien-1 -yl acetate, Z-7- tetradecen-2-one, Z-9-tetradecen-1 -yl acetate, Z-1 1 -tetradecenal, Z-1 1 -tetradecen-1 -ol, extract of Chenopodium ambrosiodes, Neem oil, Quillay extract;
L5) Microbial pesticides with plant stress reducing, plant growth regulator, plant growth promoting and/or yield enhancing activity: Azospirillum amazonense, A. brasilense, A. lipoferum, A. irakense, A. halopraeferens, Bradyrhizobium spp., B. elkanii, B. japoni- cum, B. liaoningense, B. lupini, Delftia acidovorans, Glomus intraradices, Mesorhizo- bium spp., Rhizobium leguminosarum bv. phaseoli, R. I. bv. trifolii, R. I. bv. viciae, R. tropici, Sinorhizobium meliloti;
M) Growth regulators
abscisic acid (M.1.1 ), amidochlor, ancymidol, 6-benzylaminopurine, brassinolide, butralin, chlormequat, chlormequat chloride, choline chloride, cyclanilide, daminozide, dikegulac, dime- thipin, 2,6-dimethylpuridine, ethephon, flumetralin, flurprimidol, fluthiacet, forchlorfenuron, gib- berellic acid, inabenfide, indole-3-acetic acid , maleic hydrazide, mefluidide, mepiquat, mepiquat chloride, naphthaleneacetic acid, N-6-benzyladenine, paclobutrazol, prohexadione, prohexadi- one-calcium, prohydrojasmon, thidiazuron, triapenthenol, tributyl phosphorotrithioate,
2,3,5-tri-iodobenzoic acid , trinexapac-ethyl and uniconazole;
N) Herbicides from classes N.1 to N.15
N.1 Lipid biosynthesis inhibitors: alloxydim, alloxydim-sodium, butroxydim, clethodim,
clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop- methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P, fenoxaprop-P-ethyl, fluazifop, fluazifop- butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P- methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, sethoxydim, tepra- loxydim, tralkoxydim, 4-(4'-chloro-4-cyclo-,propyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-5-hydroxy- 2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337-72-6); 4-(2',4'-dichloro-4-cyclopro- pyl[1 ,1 '-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS 1312337- 45-3); 4-(4'-chloro-4-ethyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-py- ran-3(6H)-one (CAS 1033757-93-5); 4-(2',4'-Dichloro-4-ethyl[1 ,1 '-biphenyl]-3-yl)-2,2,6,6-tet- ramethyl-2H-pyran-3,5(4H,6H)-dione (CAS 1312340-84-3); 5-(acetyloxy)-4-(4'-chloro-4-cy- clopropyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312337-48-6); 5-(acetyloxy)-4-(2',4'-dichloro-4-cyclopropyl- [1 ,1 '-biphenyl]-3-yl)-3,6-dihy- dro-2,2,6,6-tetramethyl-2H-pyran-3-one; 5-(acetyloxy)-4-(4'-chloro-4-ethyl-2'-fluoro[1 ,1 '-bi- phenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS 1312340-82-1 ); 5-(acet- yloxy)-4-(2',4'-dichloro-4-ethyl[1 ,1 '-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-
3- one (CAS 1033760-55-2); 4-(4'-chloro-4-cyclopropyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)-5,6-dihy- dro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1312337-51 -1 );
4- (2',4'-dichloro -4-cyclopropyl- [1 ,1 '-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-
2H-pyran-3-yl carbonic acid methyl ester; 4-(4'-chloro-4-ethyl-2'-fluoro[1 ,1 '-biphenyl]-3-yl)- 5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonic acid methyl ester (CAS 1312340-83-2); 4-(2',4'-dichloro-4-ethyh[1 ,1 '-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl- 5-0X0-2 H-pyran-3-yl carbonic acid methyl ester (CAS 1033760-58-5); benfuresate, butylate, cycloate, dalapon, dimepiperate, EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, thiobencarb, tiocarbazil, triallate and vernolate; N.2 ALS inhibitors: amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethamet- sulfuron-methyl, ethoxysulfuron, flazasulfuron, flucetosulfuron, flupyrsulfuron, flupyrsulfuron- methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosulfu- ron, iodosulfuron-methyl-sodium, iofensulfuron, iofensulfuron-sodium, mesosulfuron, met- azosulfuron, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron, pyrazosul- furon-ethyl, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron, thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfu- ron, triflusulfuron-methyl, tritosulfuron, imazamethabenz, imazamethabenz-methyl, imaza- mox, imazapic, imazapyr, imazaquin, imazethapyr; cloransulam, cloransulam-methyl, di- closulam, flumetsulam, florasulam, metosulam, penoxsulam, pyrimisulfan and pyroxsulam; bispyribac, bispyribac-sodium, pyribenzoxim, pyriftalid, pyriminobac, pyriminobac-methyl, py- rithiobac, pyrithiobac-sodium, 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]- benzoic acid-1 -methyhethyl ester (CAS 420138-41 -6), 4-[[[2-[(4,6-dimethoxy-2-pyrimidi- nyl)oxy]phenyl]-"methyl]amino]-benzoic acid propyl ester (CAS 420138-40-5), N-(4-bromo- phenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzenemethanamine (CAS 420138-01 -8); flu- carbazone, flucarbazone-sodium, propoxycarbazone, propoxycarbazone-sodium, thien- carbazone, thiencarbazone-methyl; triafamone;
N.3 Photosynthesis inhibitors: amicarbazone; chlorotriazine; ametryn, atrazine, chloridazone, cyanazine, desmetryn, dimethametryn,hexazinone, metribuzin, prometon, prometryn, pro- pazine, simazine, simetryn, terbumeton, terbuthylazin, terbutryn, trietazin; chlorobromuron, chlorotoluron, chloroxuron, dimefuron, diuron, fluometuron, isoproturon, isouron, linuron, metamitron, methabenzthiazuron, metobenzuron, metoxuron, monolinuron, neburon, sidu- ron, tebuthiuron, thiadiazuron, desmedipham, karbutilat, phenmedipham, phenmedipham- ethyl, bromofenoxim, bromoxynil and its salts and esters, ioxynil and its salts and esters, bromacil, lenacil, terbacil, bentazon, bentazon-sodium, pyridate, pyridafol, pentanochlor, pro- panil; diquat, diquat-dibromide, paraquat, paraquat-dichloride, paraquat-dimetilsulfate;
N.4 protoporphyrinogen-IX oxidase inhibitors: acifluorfen, acifluorfen-sodium, azafenidin, ben- carbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlor- methoxyfen, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, flumiclorac, flumiclorac-pen- tyl, flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet-methyl, fomesafen, halosafen, lactofen, oxadiargyl, oxadiazon, oxyfluorfen, pentoxazone, profluazol, pyraclonil, pyraflufen, pyraflufen-ethyl, saflufenacil, sulfentrazone, thidiazimin, tiafenacil, trifludimoxazin, ethyl [3-[2-chloro-4-fluoro-5-(1 -methyl-6-trifluoromethyl-2,4-dioxo-1 ,2,3,4-tetrahydropyrim- idin-3-yl)phenoxy]-2-pyridyloxy]acetate (CAS 353292-31 -6), N-ethyl-3-(2,6-dichloro-4-tri- fluoro-methylphenoxy)-5-methyl-1 H-pyrazole-1 -carboxamide (CAS 452098-92-9), N tetrahy- drofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1 H-pyrazole-1 -carboxamide
(CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethyhphenoxy)-5-methyl-1 H- pyrazole-1 -carboxamide (CAS 452099-05-7), N tetrahydro-"furfuryl-3-(2-chloro-6-fluoro-4- trifluoro-,methylphenoxy)-5-methyl-1 H-pyrazole-1 -carboxamide (CAS 452100-03-7), 3-[7- fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1 ,4]oxazin-6-yl]-1 ,5-dimethyl-6-thioxo- [1 ,3,5]triazinan-2,4-dione (CAS 451484-50-7), 2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihy- dro-2H-benzo[1 ,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1 ,3-dione (CAS 13001 18-96-0), 1 -methyl-6-trifluoro^methyl-3-(2,2,7-tri-fluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-ben- zo[1 ,4]oxazin-6-yl)-1 H-pyrimidine-2,4-dione (CAS 13041 13-05-0), methyl (E)-4-[2-chloro- 5-[4-chloro-5-(difluoromethoxy)-1 H-methyl-pyrazol-3-yl]-4-fluoro-phenoxy]-3-methoxy-but- 2-enoate (CAS 948893-00-3), 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1 H-benzimidazol-4-yl]- 1 -methyl-6-(trifluoromethyl)-1 H-pyrimidine-2,4-dione (CAS 212754-02-4);
N.5 Bleacher herbicides: beflubutamid, diflufenican, fluridone, flurochloridone, flurtamone,
norflurazon, picolinafen, 4-(3-trifluoromethyhphenoxy)-2-(4-trifluoromethylphenyl)-,pyrimi- dine (CAS 180608-33-7); benzobicyclon, benzofenap, bicyclopyrone, clomazone, fenquintri- one, isoxaflutole, mesotrione, pyrasulfotole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltri- one, tembotrione, tolpyralate, topramezone; aclonifen, amitrole, flumeturon;
N.6 EPSP synthase inhibitors: glyphosate, glyphosate-isopropylammonium, glyposate-potas- sium, glyphosate-trimesium (sulfosate);
N.7 Glutamine synthase inhibitors: bilanaphos (bialaphos), bilanaphos-sodium, glufosinate, glufosinate-P, glufosinate-ammonium;
N.8 DHP synthase inhibitors: asulam;
N.9 Mitosis inhibitors: benfluralin, butralin, dinitramine, ethalfluralin, fluchloralin, oryzalin, pendi- methalin, prodiamine, trifluralin; amiprophos, amiprophos-methyl, butamiphos; chlorthal, chlorthal-dimethyl, dithiopyr, thiazopyr, propyzamide, tebutam; carbetamide, chlorpropham, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, propham;
N.10 VLCFA inhibitors: acetochlor, alachlor, butachlor, dimethachlor, dimethenamid, dimethena- mid-P, metazachlor, metolachlor, metolachlor-S, pethoxamid, pretilachlor, propachlor, prop- isochlor, thenylchlor, flufenacet, mefenacet, diphenamid, naproanilide, napropamide, napro- pamide-M, fentrazamide, anilofos, cafenstrole, fenoxasulfone, ipfencarbazone, piperophos, pyroxasulfone, isoxazoline compounds of the formulae 11.1 , II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9
II.6 II.7
II.8 ii.g
N.1 1 Cellulose biosynthesis inhibitors: chlorthiamid, dichlobenil, flupoxam, indaziflam, isoxaben, triaziflam, 1 -cyclohexyl-5-pentafluorphenyloxy-14-[1 ,2,4,6]thiatriazin-3-ylamine (CAS
175899-01 -1 );
N.12 Decoupler herbicides: dinoseb, dinoterb, DNOC and its salts;
N.13 Auxinic herbicides: 2,4-D and its salts and esters, clacyfos, 2,4-DB and its salts and esters, aminocyclopyrachlor and its salts and esters, aminopyralid and its salts such as amino- pyralid-dimethylammonium, aminopyralid-tris(2-hydroxypropyl)ammonium and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, clopyralid and its salts and esters, dicamba and its salts and esters, dichlorprop and its salts and esters, dichlorprop-P and its salts and esters, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, halauxifen and its salts and esters (CAS 943832-60-8); MCPA and its salts and esters, MCPA-thioethyl, MCPB and its salts and esters, mecoprop and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, quinclorac, quin- merac, TBA (2,3,6) and its salts and esters, triclopyr and its salts and esters, 4-amino-
3- chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylic acid, benzyl
4- amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropyridine-2-carboxylate (CAS 1390661 -72-9);
N.14 Auxin transport inhibitors: diflufenzopyr, diflufenzopyr-sodium, naptalam and naptalam-so- dium;
N.15 Other herbicides: bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, cyclopyrimorate (CAS 499223-49-3) and its salts and esters, dalapon, dazomet, difenzoquat, difenzoquat-metilsulfate, dimethipin, DSMA, dymron, endothal and its salts, etobenzanid, flurenol, flurenol-butyl, flurprimidol, fosamine, fosamine-ammonium, indanofan, maleic hydra- zide, mefluidide, metam, methiozolin (CAS 403640-27-7), methyl azide, methyl bromide, me- thyl-dymron, methyl iodide, MSMA, oleic acid, oxaziclomefone, pelargonic acid, pyributicarb, quinoclamine, tridiphane;
O) Insecticides from classes 0.1 to 0.29
0.1 Acetylcholine esterase (AChE) inhibitors: aldicarb, alanycarb, bendiocarb, benfuracarb, bu- tocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb,
propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate; acephate, aza- methiphos, azinphos-ethyl, azinphosmethyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/ DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O-(methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosa- lone, phosmet, phosphamidon, phoxim, pirimiphos- methyl, profenofos, propetamphos, pro- thiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, vamidothion;
0.2 GABA-gated chloride channel antagonists: endosulfan, chlordane; ethiprole, fipronil,
flufiprole, pyrafluprole, pyriprole;
0.3 Sodium channel modulators: acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cylclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha- cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin, del- tamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, heptafluthrin, imiprothrin, meperfluthrin, metofluthrin, momfluorothrin, permethrin, phenothrin, prallethrin, profluthrin, pyrethrin (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethylfluthrin, tetramethrin, tralomethrin and trans- fluthrin; DDT, methoxychlor;
0.4 Nicotinic acetylcholine receptor agonists (nAChR): acetamiprid, clothianidin, cycloxaprid, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam; (2E)-1 -[(6-chloropyridin-3- yl)methyl]-N'-nitro-2-pentylidenehydrazinecarboximidamide; 1 -[(6-chloropyridin-3-yl)methyl]- 7-methyl-8-nitro-5-propoxy-1 ,2,3,5,6,7-hexahydroimidazo[1 ,2-a]pyridine; nicotine;
0.5 Nicotinic acetylcholine receptor allosteric activators: spinosad, spinetoram;
0.6 Chloride channel activators: abamectin, emamectin benzoate, ivermectin, lepimectin, milbe- mectin;
0.7 Juvenile hormone mimics: hydroprene, kinoprene, methoprene; fenoxycarb, pyriproxyfen; 0.8 miscellaneous non-specific (multi-site) inhibitors: methyl bromide and other alkyl halides; chloropicrin, sulfuryl fluoride, borax, tartar emetic;
0.9 Selective homopteran feeding blockers: pymetrozine, flonicamid;
0.10 Mite growth inhibitors: clofentezine, hexythiazox, diflovidazin; etoxazole;
0.1 1 Microbial disruptors of insect midgut membranes: Bacillus thuringiensis, Bacillus sphaeri- cus and the insecticdal proteins they produce: Bacillus thuringiensis subsp. israelensis, Bacillus sphaericus, Bacillus thuringiensis subsp. aizawai, Bacillus thuringiensis subsp.
kurstaki, Bacillus thuringiensis subsp. tenebrionis, the Bt crop proteins: Cry1 Ab, Cry1 Ac, Cryl Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34/35Ab1 ;
0.12 Inhibitors of mitochondrial ATP synthase: diafenthiuron; azocyclotin, cyhexatin, fenbutatin oxide, propargite, tetradifon;
0.13 Uncouplers of oxidative phosphorylation via disruption of the proton gradient: chlorfenapyr, DNOC, sulfluramid;
0.14 Nicotinic acetylcholine receptor (nAChR) channel blockers: bensultap, cartap hydrochloride, thiocyclam, thiosultap sodium;
0.15 Inhibitors of the chitin biosynthesis type 0: bistrifluron, chlorfluazuron, diflubenzuron, flu- cycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron;
0.16 Inhibitors of the chitin biosynthesis type 1 : buprofezin;
0.17 Moulting disruptors: cyromazine;
0.18 Ecdyson receptor agonists: methoxyfenozide, tebufenozide, halofenozide, fufenozide, chromafenozide;
0.19 Octopamin receptor agonists: amitraz;
O.20 Mitochondrial complex III electron transport inhibitors: hydramethylnon, acequinocyl,
fluacrypyrim;
0.21 Mitochondrial complex I electron transport inhibitors: fenazaquin, fenpyroximate, pyrim- idifen, pyridaben, tebufenpyrad, tolfenpyrad; rotenone;
0.22 Voltage-dependent sodium channel blockers: indoxacarb, metaflumizone, 2-[2-(4-cyano- phenyl)-1 -[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]-hydrazinecar- boxamide, N-(3-chloro-2-methylphenyl)-2-[(4-chlorophenyl)-[4-[methyl(methylsulfonyl)- amino]phenyl]methylene]-hydrazinecarboxamide;
0.23 Inhibitors of the of acetyl CoA carboxylase: spirodiclofen, spiromesifen, spirotetramat; 0.24 Mitochondrial complex IV electron transport inhibitors: aluminium phosphide, calcium
phosphide, phosphine, zinc phosphide, cyanide;
0.25 Mitochondrial complex II electron transport inhibitors: cyenopyrafen, cyflumetofen;
0.26 Ryanodine receptor-modulators: flubendiamide, chlorantraniliprole, cyantraniliprole, cycla- niliprole, tetraniliprole; (R)-3-chloro-N1 -{2-methyl-4-[1 ,2,2,2 -tetrafluoro-l -(trifluoromethyl)- ethyl]phenyl}-N2-(1 -methyl-2-methylsulfonylethyl)phthalamide, (S)-3-chloro-N1 -{2-methyl-4- [1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]phenyl}-N2-(1 -methyl-2-methylsulfonylethyl)- phthalamide, methyl-2-[3,5-dibromo-2-({[3-bromo-1 -(3-chloropyridin-2-yl)-1 H-pyrazol-5-yl]- carbonyl}amino)benzoyl]-1 ,2-dimethylhydrazinecarboxylate; N-[4,6-dichloro-2-[(diethyl- lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole- 3-carboxamide; N-[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]- 2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[4-chloro-2-[(di-2-propyl- lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluorometh- yl)pyrazole-3-carboxamide; N-[4,6-dichloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carba- moyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[4,6-di- bromo-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluo- romethyl)pyrazole-3-carboxamide; N-[2-(5-amino-1 ,3,4-thiadiazol-2-yl)-4-chloro-6-meth- ylphenyl]-3-bromo-1 -(3-chloro-2-pyridinyl)-1 H-pyrazole-5-carboxamide; 3-chloro-1 -(3-chloro- 2-pyridinyl)-N-[2,4-dichloro-6-[[(1 -cyano-1 -methylethyl)amino]carbonyl]phenyl]-1 H-pyrazole- 5-carboxamide; 3-bromo-N-[2,4-dichloro-6-(methylcarbamoyl)phenyl]-1 -(3,5-dichloro-2-pyri- dyl)-1 H-pyrazole-5-carboxamide; N-[4-chloro-2-[[(1 ,1 -dimethylethyl)amino]carbonyl]-6-meth- ylphenyl]-1 -(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1 H-pyrazole-5-carboxamide; cyhalodi- amide;
0.27. insecticidal active compounds of unknown or uncertain mode of action: afidopyropen,
afoxolaner, azadirachtin, amidoflumet, benzoximate, bifenazate, broflanilide, bromopropy- late, chinomethionat, cryolite, dicloromezotiaz, dicofol, flufenerim, flometoquin, fluensulfone, fluhexafon, fluopyram, flupyradifurone, fluralaner, metoxadiazone, piperonyl butoxide, pyflu- bumide, pyridalyl, pyrifluquinazon, sulfoxaflor, tioxazafen, triflumezopyrim, 1 1 -(4-chloro- 2,6-dimethylphenyl)-12-hydroxy-1 ,4-dioxa-9-azadispiro[4.2.4.2]-tetradec-1 1 -en-10-one, 3-(4'-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1 -azaspiro[4.5]dec-3-en-2-one, 1 -[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)- zole-5-amine, Bacillus firmus; (E/Z)-N-[1 -[(6-chloro-3-pyndyl)methyl]-2-pyridylidene]-2,2,2-tri- fluoro-acetamide; (E/Z)-N-[1 -[(6-chloro-5-fluoro-3-pyndyl)methyl]-2-pyridylidene]-2,2,2-tri- fluoro-acetamide; (E/Z)-2,2,2-trifluoro-N-[1 -[(6-fluoro-3-pyridyl)methyl]-2-pyndylidene]acet- amide; (E/Z)-N-[1 -[(6-bromo-3-pyndyl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide; (E/Z)-N-[1 -[1 -(6-chloro-3-pyndyl)ethyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide; (E/Z)-N-[1 - [(6-chloro-3-pyndyl)methyl]-2-pyridylidene]-2,2-difluoro-acetamide; (E/Z)-2-chloro-N-[1 -[(6- chloro-3-pyridyl)methyl]-2-pyndylidene]-2,2-difluoro-acetamide; (E/Z)-N-[1 -[(2-chloropyrim- idin-5-yl)methyl]-2-pyridylidene]-2,2,2-trifluoro-acetamide; (E/Z)-N-[1 -[(6-chloro-3-pyridyl)me- thyl]-2-pyridylidene]-2,2,3,3,3-pentafluoro-propanamide.); N-[1 -[(6-chloro-3-pyridyl)methyl]-2- pyridylidene]-2,2,2-trifluoro-thioacetamide; N-[1 -[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]- 2,2,2-trifluoro-N'-isopropyl-acetamidine; fluazaindolizine; 4-[5-(3,5-dichlorophenyl)-5-(trifluo- romethyl)-4H-isoxazol-3-yl]-2-methyl-N-(1 -oxothietan-3-yl)benzamide; fluxametamide; 5-[3- [2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1 H-pyrazole; 3-(benzoylmethyla- mino)-N-[2-bromo-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)propyl]-6-(trifluoromethyl)^ nyl]-2-fluoro-benzamide; 3-(benzoylmethylamino)-2-fluoro-N-[2-iodo-4-[1 ,2,2,2-tetrafluoro-1 - (trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]-benzamide; N-[3-[[[2-iodo-4-[1 ,2,2,2-tetra- fluoro-1 -(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]amino]carbonyl]p
benzamide; N-[3-[[[2-bromo-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]-6-(trifluorome- thyl)phenyl]amino]carbonyl]-2-fluorophenyl]-4-fluoro-N-methyl-benzamide; 4-fluoro-N-[2- fluoro-3-[[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]-6-(trifluoromethyl)phe nyl]amino]carbonyl]phenyl]-N-methyl-benzamide; 3-fluoro-N-[2-fluoro-3-[[[2-iodo-4-[1 , 2,2,2- tetrafluoro-1 -(trifluoromethyl)ethyl]-6(trifluoromethyl)phenyl]amino]carbon
thyl-benzamide; 2-chloro-N-[3-[[[2-iodo-4-[1 ,2,2,2-tetrafluoro-1 -(trifluoromethyl)ethyl]-6-(tri- fluoromethyl)phenyl]amino]carbonyl]phenyl]-3-pyridinecarboxamide; 4-cyano-N-[2-cyano-5- [[2,6-dibromo-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)propyl]phenyl]carbamoyl]pheny ^ methyl-benzamide; 4-cyano-3-[(4-cyano-2-methyl-benzoyl)amino]-N-[2,6-dichloro-4- [1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)propyl]phenyl]-2-fluoro-benzamide; N-[5-[[2-chloro- 6-cyano-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)propyl]phenyl]carbamoyl]-2-cyano-phe- nyl]-4-cyano-2-methyl-benzamide; N-[5-[[2-bromo-6-chloro-4-[2,2,2-trifluoro-1 -hydroxy-1 -(tri- fluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzami N-[5- [[2-bromo-6-chloro-4-[1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)propyl]phenyl]carbamoyl]-2- cyano-phenyl]-4-cyano-2-methyl-benzamide; 4-cyano-N-[2-cyano-5-[[2,6-dichloro-4- [1 ,2,2,3,3,3-hexafluoro-1 -(trifluoromethyl)propyl]phenyl]carbamoyl]phenyl]-2-methyl-ben- zamide; 4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1 ,2,2,2-tetrafluoro-1 -(trifluorome- thyl)ethyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; N-[5-[[2-bromo-6-chloro-4-[1 , 2,2,2- tetrafluoro-1 -(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-m
zamide; 2-(1 ,3-dioxan-2-yl)-6-[2-(3-pyridinyl)-5-thiazolyl]-pyridine; 2-[6-[2-(5-fluoro-3-pyridi- nyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine; 2-[6-[2-(3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimi- dine; N-methylsulfonyl-6-[2-(3-pyndyl)thiazol-5-yl]pyridine-2-carboxamide; N-methylsulfonyl-
6- [2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide; N-ethyl-N-[4-methyl-2-(3-pyridyl)thiazol- 5-yl]-3-methylthio-propanamide; N-methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio- propanamide; N,2-dimethyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propanamide; N-ethyl-2-methyl-N-[4-methyl-2-(3-pyridyl)thiazol-5-yl]-3-methylthio-propanami N-[4- chloro-2-(3-pyridyl)thiazol-5-yl]-N-ethyl-2-methyl-3-methylthio-propanamide; N-[4-chloro-2- (3-pyridyl)thiazol-5-yl]-N,2-dimethyl-3-methylthio-propanamide; N-[4-chloro-2-(3-pyridyl)thia- zol-5-yl]-N-methyl-3-methylthio-propanamide; N-[4-chloro-2-(3-pyridyl)thiazol-5-yl]-N-ethyl-3- methylthio-propanamide; 1 -[(6-chloro-3-pyridinyl)methyl]-1 ,2,3,5,6,7-hexahydro-5-methoxy-
7- methyl-8-nitro-imidazo[1 ,2-a]pyridine; 1 -[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro-
1 ,2,3,5,6,7-hexahydroimidazo[1 ,2-a]pyridin-5-ol; 1-isopropyl-N,5-dimethyl-N-pyridazin-4-yl- pyrazole-4-carboxamide; 1 -(1 ,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyndazin-4-yl-pyrazole- 4-carboxamide; N,5-dimethyl-N-pyndazin-4-yl-1 -(2,2,2-trifluoro-1 -methyl-ethyl)pyrazole-4- carboxamide; 1 -[1 -(1 -cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4- carboxamide; N-ethyl-1 -(2-fluoro-1 -methyl-propyl)-5-methyl-N-pyridazin-4-yl-pyrazole-4-car- boxamide; 1 -(1 ,2-dimethylpropyl)-N,5-dimethyl-N-pyndazin-4-yl-pyrazole-4-carboxamide; 1 - [1 -(1 -cyanocyclopropyl)ethyl]-N,5-dimethyl-N-pyndazin-4-yl-pyrazole-4-carboxamide; N-me- thyl-1 -(2-fluoro-1 -methyl-propyl]-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; 1 -(4,4- difluorocyclohexyl)-N-ethyl-5-methyl-N-pyndazin-4-yl-pyrazole-4-carboxamide; 1 -(4,4-difluo- rocyclohexyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide, N-(1 -methylethyl)-2-(3- pyridinyl)-2H-indazole-4-carboxamide; N-cyclopropyl-2-(3-pyridinyl)-2H-indazole-4-carbox- amide; N-cyclohexyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide; 2-(3-pyridinyl)-N-(2,2,2-tri- fluoroethyl)-2H-indazole-4-carboxamide; 2-(3-pyridinyl)-N-[(tetrahydro-2-furanyl)methyl]-2H- indazole-5-carboxamide; methyl 2-[[2-(3-pyridinyl)-2H-indazol-5-yl]carbonyl]hydrazinecar- boxylate; N-[(2,2-difluorocyclopropyl)methyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamide; N- (2,2-difluoropropyl)-2-(3-pyridinyl)-2H-indazole-5-carboxamide; 2-(3-pyridinyl )-N-(2-pyrimidi- nylmethyl )-2H-indazole-5-carboxamide; N-[(5-methyl-2-pyrazinyl)methyl]-2-(3-pyridinyl)-2H- indazole-5-carboxamide, N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3,3,3-trifluoro- propylsulfanyl)propanamide; N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-N-ethyl-3-(3,3,3-trifluoro- propylsulfinyl)propanamide; N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-3-[(2,2-difluorocyclopro- pyl)methylsulfanyl]-N-ethyl-propanamide; N-[3-chloro-1 -(3-pyridyl)pyrazol-4-yl]-3-[(2,2-difluo- rocyclopropyl)methylsulfinyl]-N-ethyl-propanamide; sarolaner, lotilaner.
The active substances referred to as component 2, their preparation and their activity e. g. against harmful fungi is known (cf.: http://www.alanwood.net/pesticides/); these substances are commercially available. The compounds described by lUPAC nomenclature, their preparation and their pesticidal activity are also known (cf. Can. J. Plant Sci. 48(6), 587-94, 1968;
EP-A 141 317; EP-A 152 031 ; EP-A 226 917; EP-A 243 970; EP-A 256 503; EP-A 428 941 ; EP-A 532 022; EP-A 1 028 125; EP-A 1 035 122; EP-A 1 201 648; EP-A 1 122 244,
JP 2002316902; DE 19650197; DE 10021412; DE 102005009458; US 3,296,272;
US 3,325,503; WO 98/46608; WO 99/14187; WO 99/24413; WO 99/27783; WO 00/29404; WO 00/46148; WO 00/65913; WO 01/54501 ; WO 01/56358; WO 02/22583; WO 02/40431 ;
WO 03/10149; WO 03/1 1853; WO 03/14103; WO 03/16286; WO 03/53145; WO 03/61388; WO 03/66609; WO 03/74491 ; WO 04/49804; WO 04/83193; WO 05/120234; WO 05/123689; WO 05/123690; WO 05/63721 ; WO 05/87772; WO 05/87773; WO 06/15866; WO 06/87325; WO 06/87343; WO 07/82098; WO 07/90624, WO 10/139271 , WO 1 1/028657, WO 12/168188, WO 07/006670, WO 1 1/77514; WO 13/047749, WO 10/069882, WO 13/047441 , WO 03/16303, WO 09/90181 , WO 13/007767, WO 13/010862, WO 13/127704, WO 13/024009, WO 13/24010, WO 13/047441 , WO 13/162072, WO 13/092224, WO 1 1/135833, CN 1907024, CN 1456054, CN 103387541 , CN 1309897, WO 12/84812, CN 1907024, WO 09094442, WO 14/60177, WO 13/1 16251 , WO 08/013622, WO 15/65922, WO 94/01546, EP 2865265, WO 07/129454, WO 12/16551 1 , WO 1 1/081 174, WO 13/47441 ).
The present invention furthermore relates to agrochemical compositions comprising a mixture of at least one compound I (component 1 ) and at least one further active substance useful for plant protection, e. g. selected from the groups A) to O) (component 2), in particular one fur- ther fungicide, e. g. one or more fungicide from the groups A) to K), as described above, and if desired one suitable solvent or solid carrier. Those mixtures are of particular interest, since many of them at the same application rate show higher efficiencies against harmful fungi. Furthermore, combating harmful fungi with a mixture of compounds I and at least one fungicide from groups A) to K), as described above, is more efficient than combating those fungi with indi- vidual compounds I or individual fungicides from groups A) to K).
By applying compounds I together with at least one active substance from groups A) to O) a synergistic effect can be obtained, i.e. more then simple addition of the individual effects is obtained (synergistic mixtures).
This can be obtained by applying the compounds I and at least one further active substance simultaneously, either jointly (e. g. as tank-mix) or seperately, or in succession, wherein the time interval between the individual applications is selected to ensure that the active substance applied first still occurs at the site of action in a sufficient amount at the time of application of the further active substance(s). The order of application is not essential for working of the present invention.
When applying compound I and a pesticide II sequentially the time between both applications may vary e. g. between 2 hours to 7 days. Also a broader range is possible ranging from 0.25 hour to 30 days, preferably from 0.5 hour to 14 days, particularly from 1 hour to 7 days or from 1 .5 hours to 5 days, even more preferred from 2 hours to 1 day. In case of a mixture comprising a pesticide II selected from group L), it is preferred that the pesticide II is applied as last treat- ment.
According to the invention, the solid material (dry matter) of the biopesticides (with the exception of oils such as Neem oil) are considered as active components (e. g. to be obtained after drying or evaporation of the extraction or suspension medium in case of liquid formulations of the microbial pesticides).
In accordance with the present invention, the weight ratios and percentages used herein for a biological extract such as Quillay extract are based on the total weight of the dry content (solid material) of the respective extract(s).
The total weight ratios of compositions comprising at least one microbial pesticide in the form of viable microbial cells including dormant forms, can be determined using the amount of CFU
of the respective microorganism to calculate the total weight of the respective active component with the following equation that 1 x 1010 CFU equals one gram of total weight of the respective active component. Colony forming unit is measure of viable microbial cells, in particular fungal and bacterial cells. In addition, here "CFU" may also be understood as the number of (juvenile) individual nematodes in case of (entomopathogenic) nematode biopesticides, such as
Steinernema feltiae.
In the binary mixtures and compositions according to the invention the weight ratio of the component 1) and the component 2) generally depends from the properties of the active components used, usually it is in the range of from 1:10,000 to 10,000:1, often it is in the range of from 1 : 100 to 100:1, regularly in the range of from 1 :50 to 50: 1 , preferably in the range of from 1:20 to 20:1, more preferably in the range of from 1:10 to 10:1, even more preferably in the range of from 1:4 to 4:1 and in particular in the range of from 1:2 to 2:1.
According to further embodiments of the binary mixtures and compositions, the weight ratio of the component 1) and the component 2) usually is in the range of from 1000:1 to 1:1, often in the range of from 100: 1 to 1:1, regularly in the range of from 50:1 to 1:1, preferably in the range of from 20:1 to 1:1, more preferably in the range of from 10:1 to 1:1, even more preferably in the range of from 4:1 to 1:1 and in particular in the range of from 2:1 to 1:1.
According to further embodiments of the mixtures and compositions, the weight ratio of the component 1) and the component 2) usually is in the range of from 20,000:1 to 1:10, often in the range of from 10,000:1 to 1:1, regularly in the range of from 5,000:1 to 5:1, preferably in the range of from 5,000:1 to 10:1, more preferably in the range of from 2,000:1 to 30:1, even more preferably in the range of from 2,000:1 to 100:1 and in particular in the range of from 1,000:1 to 100:1.
According to a further embodiments of the binary mixtures and compositions, the weight ratio of the component 1) and the component 2) usually is in the range of from 1:1 to 1:1000, often in the range of from 1:1 to 1:100, regularly in the range of from 1:1 to 1:50, preferably in the range of from 1:1 to 1:20, more preferably in the range of from 1:1 to 1:10, even more preferably in the range of from 1:1 to 1:4 and in particular in the range of from 1:1 to 1:2.
According to further embodiments of the mixtures and compositions, the weight ratio of the component 1) and the component 2) usually is in the range of from 10:1 to 1:20,000, often in the range of from 1:1 to 1:10,000, regularly in the range of from 1:5 to 1:5,000, preferably in the range of from 1:10 to 1 :5,000, more preferably in the range of from 1 :30 to 1 :2,000, even more preferably in the range of from 1:100 to 1:2,000 to and in particular in the range of from 1:100 to 1:1,000.
In the ternary mixtures, i.e. compositions according to the invention comprising the component 1) and component 2) and a compound III (component 3), the weight ratio of component 1) and component 2) depends from the properties of the active substances used, usually it is in the range of from 1:100 to 100:1, regularly in the range of from 1:50 to 50:1, preferably in the range of from 1:20 to 20:1, more preferably in the range of from 1:10 to 10:1 and in particular in the range of from 1:4 to 4:1, and the weight ratio of component 1) and component 3) usually it is in the range of from 1:100 to 100:1, regularly in the range of from 1:50 to 50:1, preferably in the range of from 1:20 to 20:1, more preferably in the range of from 1:10 to 10:1 and in particular in the range of from 1 :4 to 4:1.
Any further active components are, if desired, added in a ratio of from 20:1 to 1 :20 to the
component 1 ).
These ratios are also suitable for inventive mixtures applied by seed treatment.
When mixtures comprising microbial pesticides are employed in crop protection, the applica- tion rates preferably range from about 1 x 106 to 5 x 1016 (or more) CFU/ha, preferably from about 1 x 108 to about 1 x 1013 CFU/ha, and even more preferably from about 1 x 103 to 5 x 1015 CFU/ha and particularly preferred even more preferably from 1 x 1012 to 5 x 1014 CFU/ha. In the case of (entomopathogenic) nematodes as microbial pesticides (e. g. Steinernema feltiae), the application rates preferably range inform about 1 x 105 to 1 x 1012 (or more), more preferably from 1 x 108 to 1 x 1011, even more preferably from 5 x 108 to 1 x 1010 individuals (e. g. in the form of eggs, juvenile or any other live stages, preferably in an infetive juvenile stage) per ha.
When mixtures comprising microbial pesticides are employed in seed treatment, the application rates with respect to plant propagation material preferably range from about 1 x 106 to 1 x 1012 (or more) CFU/seed. Preferably, the concentration is about 1 x 106 to about 1 x 103 CFU/seed. In the case of the microbial pesticides II, the application rates with respect to plant propagation material also preferably range from about 1 x 107 to 1 x 1014 (or more) CFU per 100 kg of seed, preferably from 1 x 103 to about 1 x 1012 CFU per 100 kg of seed.
Preference is also given to mixtures comprising as component 2) at least one active sub- stance selected from inhibitors of complex III at Q0 site in group A), more preferably selected from compounds (A.1 .1 ), (A.1 .4), (A.1 .8), (A.1 .9), (A.1.10), (A.1.12), (A.1 .13), (A.1.14), (A.1.17), (A.1.21 ), (A.1 .24), (A.1.25), (A.1.26), (A.1 .27), (A.1.30), (A.1 .31 ), (A.1 .32), (A.1.34) and
(A.1.35); particularly selected from (A.1.1 ), (A.1.4), (A.1.8), (A.1.9), (A.1.13), (A.1 .14), (A.1 .17), (A.1.24), (A.1.25), (A.1 .26), (A.1.27), (A.1.30), (A.1 .31 ), (A.1.32), (A.1 .34) and (A.1 .35).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from inhibitors of complex III at Q, site in group A), more preferably selected from compounds (A.2.1 ), (A.2.3) and (A.2.4); particularly selected from (A.2.3) and (A.2.4).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from inhibitors of complex II in group A), more preferably selected from com- pounds (A.3.2), (A.3.3), (A.3.4), (A.3.7), (A.3.9), (A.3.1 1 ), (A.3.12), (A.3.15), (A.3.16), (A.3.17), (A.3.18), (A.3.19), (A.3.20), (A.3.21 ), (A.3.22), (A.3.23), (A.3.24), (A.3.25), (A.3.27), (A.3.28), (A.3.29), (A.3.31 ), (A.3.32), (A.3.33), (A.3.34), (A.3.35), (A.3.36), (A.3.37), (A.3.38) and
(A.3.39); particularly selected from (A.3.2), (A.3.3), (A.3.4), (A.3.7), (A.3.9), (A.3.12), (A.3.15), (A.3.17), (A.3.19), (A.3.22), (A.3.23), (A.3.24), (A.3.25), (A.3.27), (A.3.29), (A.3.31 ), (A.3.32), (A.3.33), (A.3.34), (A.3.35), (A.3.36), (A.3.37), (A.3.38) and (A.3.39).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from other respiration nhibitors in group A), more preferably selected from compounds (A.4.5) and (A.4.1 1 ); in particular (A.4.1 1 ).
Preference is also given to mixtures comprising as component 2) at least one active sub- stance selected from C14 demethylase inhibitors in group B), more preferably selected from compounds (B.1 .4), (B.1.5), (B.1.8), (B.1.10), (B.1 .1 1 ), (B.1 .12), (B.1.13), (B.1 .17), (B.1.18), (B.1.21 ), (B.1 .22), (B.1.23), (B.1 .25), (B.1.26), (B.1.29), (B.1 .34), (B.1.37), (B.1 .38), (B.1.43) and (B.1.46); particularly selected from (B.1 .5), (B.1 .8), (B.1 .10), (B.1.17), (B.1.22), (B.1.23), (B.1.25), (B.1 .33), (B.1 .34), (B.1.37), (B.138), (B.1 .43) and (B.1.46).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from Delta14-reductase inhibitors in group B), more preferably selected from compounds (B.2.4), (B.2.5), (B.2.6) and (B.2.8); in particular (B.2.4).
Preference is also given to mixtures comprising as component 2) at least one active sub- stance selected from phenylamides and acyl amino acid fungicides in group C), more preferably selected from compounds (C.1.1 ), (C.1 .2), (C.1.4) and (C.1 .5); particularly selected from (C.1.1 ) and (C.1.4).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from other nucleic acid synthesis inhibitors in group C), more preferably se- lected from compounds (C.2.6),(C.2.7) and (C.2.8).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from group D), more preferably selected from compounds (D.1.1 ), (D.1 .2), (D.1 .5), (D.2.4) and (D.2.6); particularly selected from (D.1 .2), (D.1 .5) and (D.2.6).
Preference is also given to mixtures comprising as component 2) at least one active sub- stance selected from group E), more preferably selected from compounds (E.1 .1 ), (E.1 .3), (E.2.2) and (E.2.3); in particular (E.1 .3).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from group F), more preferably selected from compounds (F.1 .2), (F.1.4) and (F.1 .5).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from group G), more preferably selected from compounds (G.3.1 ), (G.3.3), (G.3.6), (G.5.1 ), (G.5.2), (G.5.3), (G.5.4), (G.5.5), G.5.6), G.5.7), (G.5.8), (G.5.9), (G.5.10) and (G.5.1 1 ); particularly selected from (G.3.1 ), (G.5.1 ), (G.5.2) and (G.5.3).
Preference is also given to mixtures comprising as component 2) at least one active sub- stance selected from group H), more preferably selected from compounds (H.2.2), (H.2.3),
(H.2.5), (H.2.7), (H.2.8), (H.3.2), (H.3.4), (H.3.5), (H.4.9) and (H.4.10); particularly selected from (H.2.2), (H.2.5), (H.3.2), (H.4.9) and (H.4.10).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from group I), more preferably selected from compounds (1.2.2) and (1.2.5).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from group J), more preferably selected from compounds (J.1.2), (J.1 .5), (J.1 .8), (J.1.1 1 ) and (J.1 .12); in particular (J.1 .5).
Preference is also given to mixtures comprising as component 2) at least one active substance selected from group K), more preferably selected from compounds (K.1 .41 ), (K.1.42), (K.1.44), (K.1.45), (K.1 .47) and (K.1 .49); particularly selected from (K.1.41 ), (K.1 .44), (K.1.45), (K.1.47) and (K.1 .49).
The biopesticides from group L1 ) and/or L2) may also have insecticidal, acaricidal, mollus- cidal, pheromone, nematicidal, plant stress reducing, plant growth regulator, plant growth pro- moting and/or yield enhancing activity. The biopesticides from group L3) and/or L4) may also have fungicidal, bactericidal, viricidal, plant defense activator, plant stress reducing, plant growth regulator, plant growth promoting and/or yield enhancing activity. The biopesticides from group L5) may also have fungicidal, bactericidal, viricidal, plant defense activator, insecticidal, acaricidal, molluscidal, pheromone and/or nematicidal activity.
Many of these biopesticides have been deposited under deposition numbers mentioned herein (the prefices such as ATCC or DSM refer to the acronym of the respective culture collection, for details see e. g. here: http://www. wfcc.info/ccinfo/collection/by_acronym/), are referred to in literature, registered and/or are commercially available: mixtures of Aureobasidium pullu- lans DSM 14940 and DSM 14941 isolated in 1989 in Konstanz, Germany (e. g. blastospores in Blossom Protect® from bio-ferm GmbH, Austria), Azospirillum brasilense Sp245 originally isolated in wheat reagion of South Brazil (Passo Fundo) at least prior to 1980 (BR 1 1005; e. g. GELFIX® Gramineas from BASF Agricultural Specialties Ltd., Brazil), A. brasilense strains Ab- V5 and Ab-V6 (e. g. in AzoMax from Novozymes BioAg Produtos papra Agricultura Ltda., Quat- tro Barras, Brazil or Simbiose-Maiz® from Simbiose-Agro, Brazil; Plant Soil 331 , 413-425,
2010), Bacillus amyloliquefaciens strain AP-188 (NRRL B-50615 and B-50331 ; US 8,445,255); B. amyloliquefaciens spp. plantarum D747 isolated from air in Kikugawa-shi, Japan
(US 20130236522 A1 ; FERM BP-8234; e. g. Double Nickel™ 55 WDG from Certis LLC, USA), B. amyloliquefaciens spp. plantarum FZB24 isolated from soil in Brandenburg, Germany (also called SB3615; DSM 96-2; J. Plant Dis. Prot. 105, 181-197, 1998; e. g. Taegro® from Novo- zyme Biologicals, Inc., USA), B. amyloliquefaciens ssp. plantarum FZB42 isolated from soil in Brandenburg, Germany (DSM 231 17; J. Plant Dis. Prot. 105, 181-197, 1998; e. g. RhizoVital® 42 from AbiTEP GmbH, Germany), B. amyloliquefaciens ssp. plantarum MBI600 isolated from faba bean in Sutton Bonington, Nottinghamshire, U.K. at least before 1988 (also called 1430; NRRL B-50595; US 2012/0149571 A1 ; e. g. Integral® from BASF Corp., USA), B. amyloliquefa- ciens spp. plantarum QST-713 isolated from peach orchard in 1995 in California, U.S.A. (NRRL B-21661 ; e. g. Serenade® MAX from Bayer Crop Science LP, USA), B. amyloliquefaciens spp. plantarum TJ1000 isolated in 1992 in South Dakoda, U.S.A. (also called 1 BE; ATCC BAA-390; CA 2471555 A1 ; e. g. QuickRoots™ from TJ Technologies, Watertown, SD, USA), B. firmus CNCM 1-1582, a variant of parental strain El P-N 1 (CNCM 1-1556) isolated from soil of central plain area of Israel (WO 2009/126473, US 6,406,690; e. g. Votivo® from Bayer CropScience LP, USA), B. pumilus GHA 180 isolated from apple tree rhizosphere in Mexico (IDAC 260707- 01 ; e. g. PRO-MIX® BX from Premier Horticulture, Quebec, Canada), B. pumilus INR-7 otherwise referred to as BU-F22 and BU-F33 isolated at least before 1993 from cucumber infested by Erwinia tracheiphila (NRRL B-50185, NRRL B-50153; US 8,445,255), B. pumilus KFP9F isolated from the rhizosphere of grasses in South Africa at least before 2008 (NRRL B-50754; WO 2014/029697; e. g. BAC-UP or FUSION-P from BASF Agricultural Specialities (Pty) Ltd., South Africa), B. pumilus QST 2808 was isolated from soil collected in Pohnpei, Federated States of Micronesia, in 1998 (NRRL B-30087; e. g. Sonata® or Ballad® Plus from Bayer Crop Science LP, USA), B. simplex ABU 288 (NRRL B-50304; US 8,445,255), B. subtilis FB17 also called UD 1022 or UD10-22 isolated from red beet roots in North America (ATCC PTA-1 1857; System. Appl. Microbiol. 27, 372-379, 2004; US 2010/0260735; WO 201 1/109395); B. thurin- giensis ssp. aizawai ABTS-1857 isolated from soil taken from a lawn in Ephraim, Wisconsin, U.S.A., in 1987 (also called ABG-6346; ATCC SD-1372; e. g. XenTari® from BioFa AG, Mun- singen, Germany), B. t. ssp. kurstaki ABTS-351 identical to HD-1 isolated in 1967 from diseased Pink Bollworm black larvae in Brownsville, Texas, U.S.A. (ATCC SD-1275; e. g. Dipel® DF from Valent Biosciences, IL, USA), B. t. ssp. kurstaki SB4 isolated from E. saccharina larval cadavers (NRRL B-50753; e. g. Beta Pro® from BASF Agricultural Specialities (Pty) Ltd., South Africa), B. t. ssp. tenebrionis NB-176-1 , a mutant of strain NB-125, a wild type strain isolated in
1982 from a dead pupa of the beetle Tenebrio molitor (DSM 5480; EP 585 215 B1 ; e. g. Novo- dor® from Valent Biosciences, Switzerland), Beauveria bassiana GHA (ATCC 74250; e. g. BotaniGard® 22WGP from Laverlam Int. Corp., USA), B. bassiana JW-1 (ATCC 74040; e. g. Naturalis® from CBC (Europe) S.r.l., Italy), B. bassiana PPRI 5339 isolated from the larva of the tortoise beetle Conchyloctenia punctata (NRRL 50757; e. g. Broad Band® from BASF Agricultural Specialities (Pty) Ltd., South Africa), Bradyrhizobium elkanii strains SEMIA 5019 (also called 29W) isolated in Rio de Janeiro, Brazil and SEMIA 587 isolated in 1967 in the State of Rio Grande do Sul, from an area previously inoculated with a North American isolate, and used in commercial inoculants since 1968 (Appl. Environ. Microbiol. 73(8), 2635, 2007; e. g. GELFIX 5 from BASF Agricultural Specialties Ltd., Brazil), B. japonicum 532c isolated from Wisconsin field in U.S.A. (Nitragin 61A152; Can. J. Plant. Sci. 70, 661 -666, 1990; e. g. in Rhizoflo®, Histick®, Hicoat® Super from BASF Agricultural Specialties Ltd., Canada), B. japonicum E-109 variant of strain USDA 138 (INTA E109, SEMIA 5085; Eur. J. Soil Biol. 45, 28-35, 2009; Biol. Fertil. Soils 47, 81-89, 201 1 ); B. japonicum strains deposited at SEMIA known from Appl. Envi- ron. Microbiol. 73(8), 2635, 2007: SEMIA 5079 isolated from soil in Cerrados region, Brazil by Embrapa-Cerrados used in commercial inoculants since 1992 (CPAC 15; e. g. GELFIX 5 or ADHERE 60 from BASF Agricultural Specialties Ltd., Brazil), B. japonicum SEMIA 5080 obtained under lab condtions by Embrapa-Cerrados in Brazil and used in commercial inoculants since 1992, being a natural variant of SEMIA 586 (CB1809) originally isolated in U.S.A. (CPAC 7; e. g. GELFIX 5 or ADHERE 60 from BASF Agricultural Specialties Ltd., Brazil); Burkholderia sp. A396 isolated from soil in Nikko, Japan, in 2008 (NRRL B-50319; WO 2013/032693; Marrone Bio Innovations, Inc., USA), Coniothyrium m/n/fans CON/M/91 -08 isolated from oilseed rape (WO 1996/021358; DSM 9660; e. g. Contans® WG, Intercept® WG from Bayer CropScience AG, Germany), harpin (alpha-beta) protein (Science 257, 85-88, 1992; e. g. Messenger™ or HARP-N-Tek from Plant Health Care pic, U.K.), Helicoverpa armigera nucleopolyhedrovirus (HearNPV) (J. Invertebrate Pathol. 107, 1 12-126, 201 1 ; e. g. Helicovex® from Adermatt Biocontrol, Switzerland; Diplomata® from Koppert, Brazil; Vivus® Max from AgBiTech Pty Ltd., Queensland, Australia), Helicoverpa zea single capsid nucleopolyhedrovirus (HzSNPV) (e. g. Gemstar® from Certis LLC, USA), Helicoverpa zea nucleopolyhedrovirus ABA-NPV-U (e. g. Heligen® from AgBiTech Pty Ltd., Queensland, Australia), Heterorhabditis bacteriophora (e. g. Nemasys® G from BASF Agricultural Specialities Limited, UK), Isaria fumosorosea Apopka-97 isolated from mealy bug on gynura in Apopka, Florida, U.S.A. (ATCC 20874; Biocontrol Science Technol. 22(7), 747-761 , 2012; e. g. PFR-97™ or PreFeRal® from Certis LLC, USA), Metarhi- zium anisopliae var. anisopliae F52 also called 275 or V275 isolated from codling moth in Aus- tria (DSM 3884, ATCC 90448; e. g. Met52® Novozymes Biologicals BioAg Group, Canada), Metschnikowia fructicola 277 isolated from grapes in the central part of Israel (US 6,994,849; NRRL Y-30752; e. g. formerly Shemer® from Agrogreen, Israel), Paecilomyces Hacinus 25'\ isolated from infected nematode eggs in the Philippines (AGAL 89/030550; W01991/02051 ; Crop Protection 27, 352-361 , 2008; e. g. BioAct®from Bayer CropScience AG, Germany and
MeloCon® from Certis, USA), Paenibacillus alvei NAS6G6 isolated from the rhizosphere of grasses in South Africa at least before 2008 (WO 2014/029697; NRRL B-50755; e.g. BAC-UP from BASF Agricultural Specialities (Pty) Ltd., South Africa), Pasteuria nishizawae Pn1 isolated from a soybean field in the mid-2000s in Illinois, U.S.A. (ATCC SD-5833; Federal Register 76(22), 5808, February 2, 201 1 ; e.g. Clariva™ PN from Syngenta Crop Protection, LLC, USA),
Penicillium bilaiae (also called P. bilaii) strains ATCC 18309 (= ATCC 74319), ATCC 20851 and/or ATCC 22348 (= ATCC 74318) originally isolated from soil in Alberta, Canada (Fertilizer Res. 39, 97-103, 1994; Can. J. Plant Sci. 78(1 ), 91 -102, 1998; US 5,026,417,
WO 1995/017806; e. g. Jump Start®, Provide® from Novozymes Biologicals BioAg Group, Can- ada), Reynoutria sachalinensis extract (EP 0307510 B1 ; e. g. Regalia® SC from Marrone Bioln- novations, Davis, CA, USA or Milsana® from BioFa AG, Germany), Steinernema carpocapsae (e. g. Millenium® from BASF Agricultural Specialities Limited, UK), S. feltiae (e. g. Nemashield® from BioWorks, Inc., USA; Nemasys® from BASF Agricultural Specialities Limited, UK), Strepto- myces microflavus NRRL B-50550 (WO 2014/124369; Bayer CropScience, Germany), Tricho- derma asperelloides JM41 R isolated in South Africa (NRRL 50759; also referred to as T. fertile; e. g. Trichoplus® from BASF Agricultural Specialities (Pty) Ltd., South Africa), T. harzianum l- 22 also called KRL-AG2 (ATCC 20847; BioControl 57, 687-696, 2012; e. g. Plantshield® from BioWorks Inc., USA or SabrEx™ from Advanced Biological Marketing Inc., Van Wert, OH, USA).
According to one embodiment of the inventive mixtures, the at least one pesticide II is selected from the groups L1 ) to L5):
L1 ) Microbial pesticides with fungicidal, bactericidal, viricidal and/or plant defense activator activity: Aureobasidium pullulans DSM 14940 and DSM 14941 (L1 .1 ), Bacillus amyloliquefa- ciens AP-188 (L.1 .2), B. amyloliquefaciens ssp. plantarum D747 (L.1.3), B. amyloliquefa- ciens ssp. plantarum FZB24 (L.1.4), B. amyloliquefaciens ssp. plantarum FZB42 (L.1.5), B. amyloliquefaciens ssp. plantarum MBI600 (L.1 .6), B. amyloliquefaciens ssp. plantarum QST-713 (L.1 .7), B. amyloliquefaciens ssp. plantarum TJ 1000 (L.1 .8), B. pum/'/us GB34 (L.1.9), B. pumilus GHA 180 (L.1 .10), B. pumilus INR-7 (L.1 .1 1 ), B. pumilus KFP9F
(L.1.12), B. pumilus QSJ 2808 (L.1 .13), B. simplex ABU 288 (L.1.14), B. subtilis FB17
(L.1 .15), Coniothyrium minitans CON/M/91 -08 (L.1 .16), Metschnikowia fructicola NRRL Y-30752 (L.1.17), Paenibacillus a/ve/' NAS6G6 (L.1.18), Penicillium bilaiae ATCC 22348 (L.1.19), P. bilaiae ATCC 20851 (L.1.20), Penicillium bilaiae ATCC 18309 (L.1.21 ), Strepto- myces microflavus NRRL B-50550 (L.1.22), Trichoderma asperelloides JM41 R (L.1.23), T. harzianum T-22 (L.1 .24);
L2) Biochemical pesticides with fungicidal, bactericidal, viricidal and/or plant defense activator activity: harpin protein (L.2.1 ), Reynoutria sachalinensis extract (L.2.2);
L3) Microbial pesticides with insecticidal, acaricidal, molluscidal and/or nematicidal activity: Bacillus firmus 1-1582 (L.3.1 ); B. thuringiensis ssp. aizawai ABTS-1857 (L.3.2), B. t. ssp.
/o/rsfa/ /ABTS-351 (L.3.3), B. t. ssp. kurstaki SB4 (L.3.4), B. t. ssp. tenebrionis NB-176-1
(L.3.5), Beauveria bassiana GHA (L.3.6), B. bassiana JW-1 (L.3.7), B. bassiana PPRI 5339 (L.3.8), Burkholderia sp. A396 (L.3.9), Helicoverpa armigera nucleopolyhedrovirus
(HearNPV) (L.3.10), Helicoverpa zea nucleopolyhedrovirus (HzNPV) ABA-NPV-U (L.3.1 1 ), Helicoverpa zea single capsid nucleopolyhedrovirus (HzSNPV) (L.3.12), Heterohabditis bacteriophora (L.3.13), Isaria fumosorosea Apopka-97 (L.3.14), Metarhizium anisopliae var. anisopliae F52 (L.3.15), Paecilomyces lilacinus 251 (L.3.16), Pasteuria nishizawae Pn1 (L.3.17), Steinernema carpocapsae (L.3.18), S. feltiae (L.3.19);
L4) Biochemical pesticides with insecticidal, acaricidal, molluscidal, pheromone and/or nematicidal activity: cis-jasmone (L.4.1 ), methyl jasmonate (L.4.2), Quillay extract (L.4.3);
L5) Microbial pesticides with plant stress reducing, plant growth regulator, plant growth promoting and/or yield enhancing activity: Azospirillum brasilense Ab-V5 and Ab-V6 (L.5.1 ), A. bra- s/'/ense Sp245 (L.5.2), Bradyrhizobium elkanii SEMA 587 (L.5.3), B. elkanii SEMA 5019 (L.5.4), B. japonicum 532c (L.5.5), B. japonicum E-109 (L.5.6), B. japonicum SEMIA 5079 (L.5.7), B. japonicum SEMIA 5080 (L.5.8).
The present invention furthermore relates to agrochemical compositions comprising a mixture of XXX (component 1 ) and at least one biopesticide selected from the group L)
(component 2), in particular at least one biopesticide selected from the groups L1 ) and L2), as described above, and if desired at least one suitable auxiliary.
The present invention furthermore relates to agrochemical compositions comprising a mixture of XXX (component 1 ) and at least one biopesticide selected from the group L)
(component 2), in particular at least one biopesticide selected from the groups L3) and L4), as described above, and if desired at least one suitable auxiliary.
Preference is also given to mixtures comprising as pesticide II (component 2) a biopesticide selected from the groups L1 ), L3) and L5), preferably selected from strains denoted above as (L.1.2), (L.1.3), (L.1.4), (L.1 .5), (L.1 .6), (L.1.7), (L.1.8), (L.1.10), (L.1 .1 1 ), (L.1.12), (L.1.13), (L.1.14), (L.1.15), (L.1 .17), (L.1 .18), (L.1.19), (L.1 .20), (L.1.21 ), (L.3.1 ); (L.3.9), (L.3.16), (L.3.17), (L.5.1 ), (L.5.2), (L.5.3), (L.5.4), (L.5.5), (L.5.6), (L.5.7), (L.5.8); (L.4.2), and (L.4.1 ); even more preferably selected from (L.1 .2), (L.1 .6), (L.1.7), (L.1.8), (L.1.1 1 ), (L.1 .12), (L.1.13), (L.1.14), (L.1.15), (L.1 .18), (L.1.19), (L.1 .20), (L.1.21 ), (L.3.1 ); (L.3.9), (L.3.16), (L.3.17), (L.5.1 ), (L.5.2), (L.5.5), (L.5.6); (L.4.2), and (L.4.1 ). These mixtures are particularly suitable for treatment of propagation materials, i. e. seed treatment purposes and likewise for soil treatment. These seed treatment mixtures are particularly suitable for crops such as cereals, corn and
leguminous plants such as soybean.
Preference is also given to mixtures comprising as pesticide II (component 2) a biopesticide selected from the groups L1 ), L3) and L5), preferably selected from strains denoted above as (L1.1 ), (L.1.2), (L.1 .3), (L.1 .6), (L.1 .7), (L.1.9), (L.1.1 1 ), (L.1 .12), (L.1.13), (L.1 .14), (L.1.15), (L.1.17), (L.1 .18), (L.1.22), (L.1 .23), (L.1.24), (L.2.2); (L.3.2), (L.3.3), (L.3.4), (L.3.5), (L.3.6), (L.3.7), (L.3.8), (L.3.10), (L.3.1 1 ), (L.3.12), (L.3.13), (L.3.14), (L.3.15), (L.3.18), (L.3.19); (L.4.2), even more preferably selected from (L.1.2), (L.1 .7), (L.1 .1 1 ), (L.1.13), (L.1 .14), (L.1.15), (L.1.18), (L.1 .23), (L.3.3), (L.3.4), (L.3.6), (L.3.7), (L.3.8), (L.3.10), (L.3.1 1 ), (L.3.12), (L.3.15), and (L.4.2). These mixtures are particularly suitable for foliar treatment. These mixtures for foliar treatment are particularly suitable for vegetables, fruits, vines, cereals, corn, leguminous crops such as soybeans.
The mixtures of active substances can be prepared as compositions comprising besides the active ingredients at least one inert ingredient (auxiliary) by usual means, e. g. by the means given for the compositions of compounds I. Concerning usual ingredients of such compositions reference is made to the explanations given for the compositions containing compounds I.
According to one embodiment, the microbial pesticides selected from groups L1 ), L3) and L5) embrace not only the isolated, pure cultures of the respective microorganism as defined herein, but also its cell-free extract, its suspensions in a whole broth culture or as a metabolite-
containing culture medium or a purified metabolite obtained from a whole broth culture of the microorganism.
When living microorganisms, such as pesticides II from groups L1 ), L3) and L5), form part of the compositions, such compositions can be prepared as compositions comprising besides the active ingredients at least one auxiliary by usual means (e. g. H.D. Burges: Formulation of Mico- bial Biopesticides, Springer, 1998). Suitable customary types of such compositions are suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof. Examples for composition types are suspensions, capsules, pastes, pastilles, wettable powders or dusts, pressings, granules, insecticidal articles, as well as gel formulations. Herein, it has to be taken into account that each formulation type or choice of auxiliary should not influence the viability of the microorganism during storage of the composition and when finally applied to the soil, plant or plant propagation material. Suitable formulations are e. g. mentioned in WO 2008/002371 , US 6955,912, US 5,422,107.
Synthesis example
HPLC-MS: HPLC-column Kinetex XB C18 1 ,7μ (50 x 2,1 mm); eluent: acetonitrile / water + 0.1 % TFA (5 gradient from 5:95 to 100 : 0 in 1.5 min at 60°C, flow gradient from 0.8 to 1.0 ml/min in 1 .5 min). MS: Quadrupol Electrospray lonisation, 80 V (positive mode).
Example 1 ) Synthesis of 4-(5,6-dimethyl-3-pyridyl)-2,2-dimethyl-1 ,4-benzothiazin-3-one
1 . Synthesis of 2,2-dimethyl-4/-/-1 ,4-benzothiazin-3-one
A mixture of 2-aminobenzenethiol (1 .000 g, 8.0 mmol), ethyl 2-bromo-2-methyl-propanoate (1 .714 g, 8.8 mmol), and K2C03 (1 .435 g, 10.4 mmol) in DMF (8 ml.) was stirred for 4 h at 120 °C. Water was added, the precipitate was filtered off, washed with water and diisopropyl ether and dried in vacuo to give the tittle compound (1.340 g, 87%) as a purple powder.
2. Synthesis of 4-(5,6-dimethyl-3-pyridyl)-2,2-dimethyl-1 ,4-benzothiazin-3-one
A mixture of 2,2-dimethyl-4H-1 ,4-benzothiazin-3-one (195 mg, 1 .0 mmol) in (H3C)2SO (4 ml.) was treated with K2C03 (172 mg, 1.2 mmol) and Cul (20 mg, 0.1 mmol) and stirred at 25 °C for 30 min. 5-Bromo-2,3-dimethyl-pyridine (250 mg, 1 .3 mmol) was added and the mixture was stirred for 5 h at 175 °C. Water was added and the the mixture was extracted with TBME three times. The combined organic phases were washed with water and brine, dried over Na2S04 and evaporated. Purification via column chromatography (gradient: n-heptane→ ethyl acetate) gave the tittle compound (104 mg, 34%) as a colorless oil.
With due modification of the starting compounds, the procedures shown in the synthesis exam- pies below were used to obtain further compounds I. The resulting compounds, together with physical data, are listed in Table I below.
Table I:
The positions of the heteroaryls given as "R5+R6" marked with "#" represents the connection points with the remaining skeleton of the compounds of formula
II. Biological trials
11.1 Green House
The spray solutions were prepared in several steps:
The stock solutions were prepared: a mixture of acetone and/or dimethylsulfoxide and the wetting agent/emulsifier Wettol, which is based on ethoxylated alkylphenoles, in a relation (volume) sol- vent-emulsifier of 99 to 1 was added to 25 mg of the compound to give a total of 5 ml.
Water was then added to total volume of 100 ml.
This stock solution was diluted with the described solvent-emulsifier-water mixture to the given concentration.
Example 1 - Preventative fungicidal control of Botrytis cinerea on leaves of green pepper
Young seedlings of green pepper were grown in pots to the 4 to 5 leaf stage. These plants were sprayed to run-off with an aqueous suspension, containing the concentration of active ingredient or their mixture mentioned in the table below. The next day the plants were inoculated with an aqueous biomalt or DOB solution containing the spore suspension of Botrytis cinerea. Then the plants were immediately transferred to a humid chamber. After 5 days at 22 to 24· C and a relative humidity close to 100 % the extent of fungal attack on the leaves was visually assessed as % diseased leaf area.
In this test, the samples which had been treated with 250 ppm of the active substance from example 1-1 showed up to at mostl 4 % growth of the pathogen whereas the untreated plants were 90% infected.
11.2 Microtest
The active compounds were formulated separately as a stock solution having a concentration of 10000 ppm in dimethyl sulfoxide.
Example 1 - Activity against the grey mold Botrytis cinerea in the microtiterplate test
The stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations. A spore suspension of Botrci cinerea in an aqueous biomalt or yeast-bactopeptone-sodiumacetate solution was then added. The plates were placed in a water vapor-saturated chamber at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm 7 days after the inoculation.
In this test, the samples which had been treated with 31 ppm of the active substance from 1-1 showed up to at most 5 % growth of the pathogen.
Example 2 - Activity against rice blast Pyricularia oryzae in the microtiterplate test
The stock solutions were mixed according to the ratio, pipetted onto a micro titer plate (MTP) and diluted with water to the stated concentrations. A spore suspension of Pyricularia oryzae in an aqueous biomalt or yeast-bactopeptone-glycerine solution was then added. The plates were placed in a water vapor-saturated chamber at a temperature of 18°C. Using an absorption photometer, the MTPs were measured at 405 nm 7 days after the inoculation
In this test, the samples which had been treated with 31 ppm of the active substance from 1-1 and I-2 respectively, showed up to at most 1 % growth of the pathogen.
The measured parameters were compared to the growth of the active compound-free control variant (100%) and the fungus-free and active compound-free blank value to determine the relative growth in % of the pathogens in the respective active compounds.
Claims
1 . Use of compounds of formula I
is in each case independently selected from H, halogen, OH, CN, NO2, SH, NH2, NH(Ci- C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6- alkoxy, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the het- eroaryl contains one, two or three heteroatoms selected from N, O and S; wherein
Rx is Ci-C4-alkyl, Ci-C4-halogenalkyl, unsubstituted aryl or aryl that is substituted with substituents Rx1 independently selected from Ci-C4-alkyl, halogen, OH, CN, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the acyclic moieties of R1 are unsubstituted or substituted with groups R1a which independently of one another are selected from:
R1a halogen, OH, CN , Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4- halogenalkoxy, Ci-C6-alkylthio, aryl and phenoxy, wherein the aryl and phenoxy group is unsubstituted or substituted with substituents R11a selected from the group consisting of halogen, OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the carbocyclic, heteroaryl and aryl moieties of R1 are unsubstituted or substituted with groups R1 b which independently of one another are selected from:
R1 b halogen, OH, CN , Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio; is in each case independently selected from H, halogen, OH, CN, NO2, SH, NH2, NH(Ci- C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6- alkoxy, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; wherein Rx is as defined above;
wherein the acyclic moieties of R2 are unsubstituted or substituted with groups R2a which independently of one another are selected from:
R2a halogen, OH, CN , Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci- C4-halogenalkoxy, Ci-C6-alkylthio, aryl and phenoxy, wherein the aryl and phenoxy group is unsubstituted or substituted with substituents R22a selected from
the group consisting of halogen, OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, C1-C4- alkoxy and Ci-C4-halogenalkoxy;
wherein the carbocyclic, heteroaryl and aryl moieties of R2 are unsubstituted or substituted with groups R2b which independently of one another are selected from:
R2b halogen, OH, CN , Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cyclo- alkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio;
is in each case independently selected from halogen, OH , CN, NO2, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, N H(C2-C4-alkenyl), N(C2-C4-alkenyl)2, N H(C2-C4-al- kynyl), N(C2-C4-alkynyl)2, N H(C3-C6-cycloalkyl), N(C3-C6-cycloalkyl)2, N(Ci-C4-alkyl)(C2- C4-alkenyl), N(Ci-C4-alkyl)(C2-C4-alkynyl), N(Ci-C4-alkyl)(C3-C6-cycloalkyl), N(C2-C4- alkenyl)(C2-C4-alkynyl), N(C2-C4-alkenyl)(C3-C6-cycloalkyl), N(C2-C4-alkynyl)(C3-C6-cyclo- alkyl), NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, S(0)n-Ci-C6-alkyl, S(0)n- aryl, d-Ce-cycloalkylthio, S(0)n-C2-C6-alkenyl, S(0)n-C2-C6-alkynyl, CH(=0), C(=0)Ci- Ce-alkyl, C(=0)C2-C6-alkenyl, C(=0)C2-C6-alkynyl, C(=0)C3-C6-cycloalkyl, C(=0)N H(Ci- Ce-alkyl), CH(=S), C(=S)Ci-C6-alkyl, C(=S)C2-C6-alkenyl, C(=S)C2-C6-alkynyl, C(=S)C3- Ce-cycloalkyl, C(=S)N H(Ci-C6-alkyl), Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2- C6-alkynyl, ORY, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; wherein Rx and n is as defined above;
RY is Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6- alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, phenyl and phenyl-Ci-C6-alkyl; wherein the phenyl groups are unsubstituted or or carry one, two, three, four or five substituents selected from the group consisting of CN, halogen, OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and C1-C4- halogenalkoxy;
wherein the acyclic moieties of R3 are unsubstituted or substituted with groups R3a which independently of one another are selected from:
R3a halogen, OH, CN , Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, C1-C4- halogenalkoxy, Ci-C6-alkylthio, aryl and phenoxy; wherein the aryl and phenoxy group is unsubstituted or substituted with substituent R31a selected from the group consisting of halogen, OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the carbocyclic, heteroaryl and aryl moieties of R3 are unsubstituted or substituted with groups R3b which independently of one another are selected from:
R3b halogen, OH, CN , Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio;
is in each case independently selected from halogen, OH , CN, NO2, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, N H(C2-C4-alkenyl), N(C2-C4-alkenyl)2, N H(C2-C4-al- kynyl), N(C2-C4-alkynyl)2, N H(C3-C6-cycloalkyl), N(C3-C6-cycloalkyl)2, N(Ci-C4-alkyl)(C2- C4-alkenyl), N(Ci-C4-alkyl)(C2-C4-alkynyl), N(Ci-C4-alkyl)(C3-C6-cycloalkyl), N(C2-C4-
alkenyl)(C2-C4-alkynyl), N(C2-C4-alkenyl)(C3-C6-cycloalkyl), N(C2-C4-alkynyl)(C3-C6-cyclo- alkyl), NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, S(0)n-Ci-C6-alkyl, S(0)n- aryl, Ci-C6-cycloalkylthio, S(0)n-C2-C6-alkenyl, S(0)n-C2-C6-alkynyl, CH(=0), C(=0)Ci- Ce-alkyl, C(=0)C2-C6-alkenyl, C(=0)C2-C6-alkynyl, C(=0)C3-C6-cycloalkyl, C(=0)NH(Ci- Ce-alkyl), CH(=S), C(=S)Ci-C6-alkyl, C(=S)C2-C6-alkenyl, C(=S)C2-C6-alkynyl, C(=S)C3-
Ce-cycloalkyl, C(=S)NH(Ci-C6-alkyl), Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2- C6-alkynyl, ORY, C3-C6-cycloalkyl, five- or six-membered heteroaryl and aryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; wherein Rx and n is as defined above;
RY is d-Ce-alkyl, C-i-Ce-halogenalkyl, C2-Ce-alkenyl, C2-C6-halogenalkenyl, C2-Ce- alkynyl, C2-C6-halogenalkynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, phenyl and phenyl-Ci-C6-alkyl; wherein the phenyl groups are unsubstituted or or carry one, two, three, four or five substituents selected from the group consisting of CN, halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4- halogenalkoxy;
wherein the acyclic moieties of R4 are unsubstituted or substituted with groups R4a which independently of one another are selected from:
R4a halogen, OH, CN, d-Ce-alkoxy, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4- halogenalkoxy, Ci-C6-alkylthio, aryl and phenoxy; wherein the aryl and phenoxy group is unsubstituted or substituted with substituent R41a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the carbocyclic, heteroaryl and aryl moieties of R4 are unsubstituted or substituted with groups R4b which independently of one another are selected from:
R4b halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl,
C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy and Ci-C6-alkylthio;
R3, R4 together with the carbon atoms to which they are bound form a five- , six-, or seven- membered carbo-, heterocyclic or heteroaromatic ring; wherein the heterocyclic or het- eroaromatic ring contains 1 , 2, 3 or 4 heteroatoms selected from N, O and S; wherein N may carry one substituent RN selected from Ci-C4-alkyl, Ci-C4-halogenalkyl and S02Ph, wherein Ph is unsubstituted or substituted with substituents selected from Ci-C4-alkyl, halogen, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy, and CN; and wherein S may be in the form of its oxide SO or S02; and wherein in each case one or two CH2 groups of the carbo- or heterocycle may be replaced by a group independently selected from C(=0) and C(=S); and wherein the carbo-, heterocyclic or heteroaromatic ring is substituent by (R34)m, wherein m is 0, 1 , 2, 3 or 4;
R34 is in each case independently selected from halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, Ci-C6-alkoxy, C3-C6-cycloalkyl, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl and aryl; wherein the heterocycle and heteroaryl contains 1 , 2 or 3 heteroatoms selected from N, O and S; and wherein in
each case one or two CH2 groups of the carbo- or heterocycle may be replaced by a group independently selected from C(=0) and C(=S); and wherein Rx is as defined above;
wherein the acyclic moieties of R34 are unsubstituted or substituted with identical or different groups R34a which independently of one another are selected from:
R34a halogen, OH, CN, d-Ce-alkoxy, Cs-Ce-cycloalkyl, Cs-Ce-halogencycloal- kyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, aryl and phenoxy; wherein the aryl and phenoxy group is unsubstituted or substituted with R341a selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogen- alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy, CN, C3-C6-cycloalkyl, C3-C6- halogencycloalkyl, Ci-C4-alkylthio;
wherein the carbocyclic, heterocyclic, heteroaryl and aryl moieties of R34 are unsubstituted or substituted with identical or different groups R34b which independently of one another are selected from:
R34b halogen, OH, CN, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, Cs-Ce- cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, and Ci-C6-al- kylthio;
, R6 together with the carbon atoms to which they are bound form a phenyl or five- or six membered heteroaryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S, and wherein the phenyl or heteroaryl is substituted with (R56)0, wherein
o is 0, 1 , 2 or 3; and
R56 are independently selected from halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-al- kyl), N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, CH(=0), C(=0)Ci-C6-alkyl, C(=0)NH(Ci-C6-alkyl), CR'=NOR", Ci-C6-alkyl, Ci-C6- halogenalkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, S(0)n- Ci-C6-alkyl, three-, four-, five- or six-membered saturated or partially unsaturated heterocycle, five- or six-membered heteroaryl and phenyl; wherein the heterocycle or heteroaryl contains one, two or three heteroatoms selected from N, O and S; wherein n and Rx are as defined above;
wherein R' and R" are independently selected from H, Ci-C4-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl or aryl; wherein the heterocycle or heteroaryl contains one, two or three heteroatoms selected from N, O and S, and wherein R' and R" are independently unsubstituted or substituted with R'" which is independently selected from halogen, OH, CN, N02, SH, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH-S02- Rx, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl, C2-C6-halogenalkenyl, C2-C6- alkynyl, C2-C6-halogenalkynyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, Cs-Ce-cycloalkyl, C3-C6-halogencycloalkyl and phenyl; wherein Rx is defined above;
and
wherein the acyclic moieties of R56 are not further substituted or carry 1 , 2, 3 or up to the maximum possible number of identical or different groups R56a which independently of one another are selected from:
R56a halogen, OH, CN , Ci-C6-alkoxy, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, C3-C6- halogencycloalkyl, C3-C6-halogencycloalkenyl, Ci-C4-halogenalkoxy, Ci-Ce-alkylthio, five- or six-membered heteroaryl, phenyl and phenoxy; wherein the het- eroaryl, phenyl and phenoxy group is unsubstituted or unsubstituted or substituted with R561a selected from the group consisting of halogen, OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
wherein the carbocyclic, phenyl, heterocyclic and heteroaryl moieties of R56 are unsubstituted or substituted with identical or different groups R56b which independently of one another are selected from:
R56b halogen, OH, CN , Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, and Ci-C6-alkylthio; is O or S;
is -C(R7R8)-S(0)p-, -C(R7R8)-0-, -C(R7R8)-NR9-, -C(R7R8)-C(=0)-, -C(R7R8)-C(=S)- or - C(R7)=N-; wherein
p is 0, 1 or 2; and
, R8 are independently selected from hydrogen, halogen, OH, CN, NO2, SH, Ci-C6-alkylthio, NH2, NH(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH-S02-Rx, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6- alkenyl, C2-C6-halogenalkenyl, C2-C6-alkynyl, C2-C6-halogenalkynyl, Ci-C6-alkoxy, C1-C6- halogenalkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, CH(=0), C(=0)Ci-C6-alkyl,
C(=0)0(Ci-C6-alkyl), C(=0)N H(Ci-C6-alkyl), C(=0)N(Ci-C6-alkyl)2, CR'=NOR", a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-mem- bered carbocycle or heterocycle, a five- or six-membered heteroaryl or aryl; wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(=0) and C(=S), and wherein the heterocycle and the heteroaryl contain independently one, two, three or four heteroatoms selected from N, O and S; and wherein Rx, R', R" and R'" are as defined above; wherein the acyclic moieties of R7 and R8 are independently not further substituted or carry 1 , 2, 3 or up to the maximum possible number of identical or different groups R7a or R8a, respectively, which independently of one another are selected from:
C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, d-C6-alkoxy, C3-C6-cycloalkyl, C3- C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci-C6-alkylthio, Ci-C6-halogen- alkylthio, S(0)n-Ci-C6-alkyl, S(0)n-aryl, CH(=0), C(=0)Ci-C6-alkyl,
Ce-alkyl), C(=0)N H(Ci-C6-alkyl), C(=0)N(Ci-C6-alkyl)2, CR'=NOR", a saturated or
partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-mem- bered carbocycle or heterocycle, aryl, phenoxy, a five-, six- or ten-membered het- eroaryl; wherein in each case one or two CH2 groups of the carbo- and heterocycle may be replaced by a group independently selected from C(=0) and C(=S); wherein the heterocycle and the heteroaryl contain independently 1 , 2, 3 or 4 het- eroatoms selected from N, O and S; wherein the carbocyclic, heterocyclic, aryl and phenyl groups are independently unsubstituted or carry one, two, three, four or five substituents selected from the group consisting of halogen, OH, CN, NO2, SH, NH2, N H(Ci-C4-alkyl), N(Ci-C4-alkyl)2, NH(C(=0)Ci-C4-alkyl),
alkyl)2, NH-S02-Rx, Ci-C6-alkylthio, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy, and S(0)n-Ci-C6-alkyl; and wherein Rx, R', R" and R'" are as defined above;
n is 0, 1 , 2;
wherein the carbocyclic, heterocyclic, heteroaryl and aryl moieties of R7 and R8 are independently not further substituted or carry 1 , 2, 3, 4, 5 or up to the maximum number of identical or different groups R7b or R8b, respectively, which independently of one another are selected from:
C4-alkyl), N(C(=0)Ci-C4-alkyl)2, NH-S02-Rx, Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-hal- ogenalkyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, Ci- Ce-alkylthio, Ci-C6-halogenalkylthio, S(0)n-Ci-C6-alkyl, Ci-C4-alkoxy-Ci-C4-alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or substituted with substituents selected from the group consisting of halogen, OH, Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy;
and wherein Rx and n is as defined above; or
, R8 together with the carbon atom to which they are bound form a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or heterocycle; wherein the heterocycle contains one, two, three or four heteroatoms selected from N, O and S, wherein the heteroatom N may carry one substituent selected from Ci-C4-alkyl, Ci-C4-halogenalkyl and S02Ph, wherein Ph is unsubstituted phenyl or phenyl that is substituted with one, two or three substituents selected from CN, C1-C4- alkyl, halogen, Ci-C4-halogenalkyl, Ci-C4-alkoxy and Ci-C4-halogenalkoxy; and wherein the heteroatom S may be in the form of its oxide SO or S02, and wherein the carbocycle or heterocycle is unsubstituted or carries one, two, three or four substituents R78 independently selected from halogen, OH, CN, N02, SH, NH2, d-Ce-alkyl, d-Ce-halogen- alkyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, Ci-C6-alkylthio, Ci-C6-halogenalkylthio, C1-C4- alkoxy-Ci-C4-alkyl, phenyl and phenoxy, wherein the phenyl groups are unsubstituted or carry one, two, three, four or five substituents R78a selected from the group consisting of CN, halogen, OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy; and wherein in each case one or two CH2 groups of the carbo- or heterocycle may be replaced by a group independently selected from C(=0) and C(=S); and
R9 is in each case independently selected from hydrogen, OH , CN , SH , N H2, N H(Ci-C4-al- kyl), N(Ci-C4-alkyl)2, N H-S02-Rx, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-C6-alkoxy, C3-C6-cycloalkyl, saturated or partially unsaturated three-, four-, five-, six-, seven, eight-, nine-, or ten-membered carbo- and heterocycle, five- or six-membered heteroaryl and aryl; wherein the heterocycle and heteroaryl contains 1 , 2 or 3 heteroatoms selected from N , O and S; and wherein in each case one or two CH2 groups of the carbo- or heterocycle may be replaced by a group independently selected from C(=0) and C(=S); and wherein
Rx is as defined above;
wherein the acyclic moieties of R9 are unsubstituted or carry 1 , 2, 3 or up to the maximum possible number of identical or different groups R9a which independently of one another are selected from:
R9a halogen, OH , CN , d-Ce-alkoxy, Cs-Ce-cycloalkyl, Cs-Ce-halogencycloalkyl, Ci- C4-halogenalkoxy, Ci-C6-alkylthio, aryl and phenoxy, wherein the aryl and phenyl group is unsubstituted or unsubstituted or substituted with R9a selected from the group consisting of halogen, OH , Ci-C4-alkyl, Ci-C4-halogenalkyl, Ci-C4-alkoxy, Ci-C4-halogenalkoxy, CN , C3-C6-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-al- kylthio;
wherein the carbocyclic, heterocyclic, heteroaryl and aryl moieties of R9 are unsubstituted or substituted with identical or different groups R9b which independently of one another are selected from:
R9b halogen, OH , CN , Ci-C4-alkyl, Ci-C4-alkoxy, Ci-C4-halogenalkyl, Cs-Ce-cycloalkyl, C3-C6-halogencycloalkyl, Ci-C4-halogenalkoxy, and Ci-C6-alkylthio; and the N-oxides and the agriculturally acceptable salts of the compounds of formula I for combating phytopathogenic fungi.
2. The use of claims 1 , wherein R1 and R2 are independently selected from H , halogen, and d-Ce-alkyl.
3. The use of any one of claims 1 to 2, wherein R3 and R4 are independently selected from CN , halogen, Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkynyl, ORY, C3-C6-cycloalkyl, Cs- Ce-halogencycloalkyl;
RY is Ci-C6-alkyl, Ci-C6-halogenalkyl, C2-C6-alkenyl or C2-C6-alkynyl.
4. The use of any one of claims 1 to 3, wherein R5 and R6 together with the carbon atoms to which they are bound form a phenyl, wherein the phenyl carries zero, one, two, three or four substituents (R56)0.
5. The use of any one of claims 1 to 3, wherein R7 and R8 together with the carbon atoms to which they are bound form a five-membered heteroaryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N , O and S, and wherein the heteroaryl carries zero, one, two, three or four substituents (R56)0.
6. The use of any one of claims 1 to 5, wherein R56 is in each case halogen, Ci-C6-alkyl, Ci-C6-halogenalkyl, Ci-C6-alkoxy, Ci-C6-halogenalkoxy, CN, C2-C6-alkenyl, C2-C6-al- kynyl, C3-C6-cycloalkyl, C3-C6-halogencycloalkyl.
7. The use of any one of claims 1 to 6, wherein A is O.
8. The use of any one of claims 1 to 7, wherein B is -C(R7R8)-S(0)p-, -C(R7R8)-0-; wherein p is 0, 1 or 2; and
R7, R8 are independently selected from hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6- alkynyl, a five- or six-membered heteroaryl or aryl; a saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine-, or ten-membered carbocycle or
heterocycle,
wherein the acyclic moieties of R7 and R8 are independently not further substituted or carry 1 , 2, 3 or up to the maximum possible number of identical or different groups R7a or R8a, respectively, which independently of one another are selected from:
R7a, R8a halogen, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl,
wherein the carbocyclic, heterocyclic, heteroaryl and aryl moieties of R7 and R8 are independently not further substituted or carry 1 , 2, 3, 4, 5 or up to the maximum number of identical or different groups R7b or R8b, respectively, which independently of one another are selected from:
R7b, R8b halogen, CN, Ci-C6-alkoxy, C3-C6-cycloalkyl;
9. Compounds of the formula I with the R1, R2, R3, R4, R5, R6, A, B, R7, R8 and R9 as defined in any one of claims 1 to 8, with the proviso that
if R3 is ORY, RY is not C2-C6-alkyl; or
if R4 is C(=0)NH(Ci-C6-alkyl), R4a is not a substituted phenyl; or
if R5 and R6 form a phenyl, R56 is not NH2 und NH-SO2-Rx.
10. A composition, comprising one compound of formula I, as defined in any of the claims 1 to 9, an N-oxide or an agriculturally acceptable salt thereof.
1 1 . The composition according to claim 10, comprising additionally a further active substance.
12. A use of a compound of the formula I, as defined in any of the claims 1 to 9, and of an agriculturally acceptable salt thereof and of the compositions, as defined in any of the claims 10 or 1 1 , for combating phytopathogenic fungi.
13. A method for combating phytopathogenic fungi, comprising treating the fungi or the materials, plants, the soil or seeds to be protected against fungal attack with an effective amount of at least one compound of formula I, as defined in any of the claims 1 to 9 or with a composition, as defined in any of the claims 10 or 1 1 .
14. Seed, coated with at least one compound of the formula I, as defined in any of the claims
1 to 9 or an agriculturally acceptable salt thereof or with a composition, as defined in any of the claims 10 or 1 1 , in an amount of from 0.1 to 10 kg per 100 kg of seed.
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US11425910B2 (en) | 2017-02-21 | 2022-08-30 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
US11839214B2 (en) | 2017-12-15 | 2023-12-12 | Basf Se | Fungicidal mixture comprising substituted pyridines |
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