EP1697367A1 - 6-(2-halogenophenyl)-triazolopyrimidines, procede pour leur production et leur utilisation pour lutter contre des champignons nuisibles, ainsi qu'agents les contenant - Google Patents
6-(2-halogenophenyl)-triazolopyrimidines, procede pour leur production et leur utilisation pour lutter contre des champignons nuisibles, ainsi qu'agents les contenantInfo
- Publication number
- EP1697367A1 EP1697367A1 EP04803941A EP04803941A EP1697367A1 EP 1697367 A1 EP1697367 A1 EP 1697367A1 EP 04803941 A EP04803941 A EP 04803941A EP 04803941 A EP04803941 A EP 04803941A EP 1697367 A1 EP1697367 A1 EP 1697367A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- formula
- compounds
- hydrogen
- cyano
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 title claims 2
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- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 245
- 239000001257 hydrogen Substances 0.000 claims abstract description 245
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 163
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 143
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 82
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 33
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 31
- 150000002367 halogens Chemical class 0.000 claims abstract description 24
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- 125000001424 substituent group Chemical group 0.000 claims abstract description 13
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- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 9
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- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 5
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 5
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
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- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 3
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- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- XRJLAOUDSILTFT-UHFFFAOYSA-N pyroquilon Chemical compound O=C1CCC2=CC=CC3=C2N1CC3 XRJLAOUDSILTFT-UHFFFAOYSA-N 0.000 description 1
- 150000004040 pyrrolidinones Chemical class 0.000 description 1
- WRPIRSINYZBGPK-UHFFFAOYSA-N quinoxyfen Chemical compound C1=CC(F)=CC=C1OC1=CC=NC2=CC(Cl)=CC(Cl)=C12 WRPIRSINYZBGPK-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Chemical group 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- MXMXHPPIGKYTAR-UHFFFAOYSA-N silthiofam Chemical compound CC=1SC([Si](C)(C)C)=C(C(=O)NCC=C)C=1C MXMXHPPIGKYTAR-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- PUYXTUJWRLOUCW-UHFFFAOYSA-N spiroxamine Chemical compound O1C(CN(CC)CCC)COC11CCC(C(C)(C)C)CC1 PUYXTUJWRLOUCW-UHFFFAOYSA-N 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000021012 strawberries Nutrition 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 150000003447 sulfenic acid derivatives Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LITQZINTSYBKIU-UHFFFAOYSA-F tetracopper;hexahydroxide;sulfate Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Cu+2].[Cu+2].[Cu+2].[Cu+2].[O-]S([O-])(=O)=O LITQZINTSYBKIU-UHFFFAOYSA-F 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- WOSNCVAPUOFXEH-UHFFFAOYSA-N thifluzamide Chemical compound S1C(C)=NC(C(F)(F)F)=C1C(=O)NC1=C(Br)C=C(OC(F)(F)F)C=C1Br WOSNCVAPUOFXEH-UHFFFAOYSA-N 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical compound COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- VJQYLJSMBWXGDV-UHFFFAOYSA-N tiadinil Chemical compound N1=NSC(C(=O)NC=2C=C(Cl)C(C)=CC=2)=C1C VJQYLJSMBWXGDV-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 235000014101 wine Nutrition 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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 substituted triazolopyrimidines of the formula I.
- R 1, R 2 independently of one another are hydrogen, C 8 alkyl, C r C 8 haloalkyl, C 3 -C 8 - cycloalkyl, C 3 -C 8 halocycloalkyl, C 2 -C 8 alkenyl, C 2 - C 8 haloalkenyl, C 3 -C 6 cycloalkenyl, C 3 -C 6 halocycloalkenyl, C 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl or phenyl, naphthyl, or a five- or six-membered saturated, partial unsaturated or aromatic heterocycle containing one to four heteroatoms from the group O, N or S,
- R 1 and R 2 can also form, together with the nitrogen atom to which they are attached, a five- or six-membered heterocyclyl or heteroaryl which is bonded via N and one to three further heteroatoms from the group O, N and S as ring member contain and / or one or more substituents from the group halogen, C r C 6 alkyl, CC 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 - haloalkenyl, -C 6 -alkoxy, C 6 Halogeno-alkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -haloalkenyloxy, C 1 -C 6 -alkylene and oxy-C 3 -C 3 -alkyienoxy;
- R 1 and / or R 2 may carry one to four identical or different groups R a :
- R a is halogen, cyano, nitro, hydroxy, CC 6 alkyl, CC 6 haloalkyl, CC 6 - alkylcarbonyl, C 3 -C 6 cycloalkyl, C r C 6 alkoxy, C Ce haloalkoxy, C
- A is hydrogen, hydroxy, d-C ⁇ -alkyl, C r C 8 alkoxy, CRCE haloalkoxy, CrC ⁇ -alkylamino or di- (CC 8 alkyl) amino;
- L 3 is hydrogen, halogen, cyano, nitro, C ⁇ -C 4 haloalkyl, CC 6 alkoxy, C r C 6 - alkoxycarbonyl;
- the invention relates to processes and intermediates for the preparation of these compounds, compositions containing them and their use for controlling phytopathogenic harmful fungi.
- EP-A 71 792, EP-A 550 113, 5-chloro-6-phenyl-7-amino-triazolopyrimidines are generally known.
- WO 03/080615 generally proposes 6-phenyltriazolopyrimidines whose phenyl group can carry an alkylamide group in the para position. These compounds are known for controlling harmful fungi.
- the compounds according to the invention differ from those described in WO 03/080615 by the position of the alkylamide group as substituent of the 6-phenyl ring.
- the object of the present invention is to provide compounds with improved activity and / or broadened spectrum of activity.
- the compounds of the invention can be obtained in various ways.
- they are prepared by reacting 5-aminotriazole of the formula II with correspondingly substituted phenylmalonates of the formula III in which R is alkyl, preferably d-C ⁇ -alkyl, in particular methyl or ethyl.
- This reaction is usually carried out at temperatures of from 80 ° C. to 250 ° C., preferably from 120 ° C. to 180 ° C., without solvent or in an inert organic solvent in the presence of a base [cf. EP-A 770 615] or in the presence of acetic acid under the conditions described in Adv. Het. Chem. Vol. 57, p. 81ff. (1993) known conditions.
- Suitable solvents are aliphatic hydrocarbons, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons, ethers, Nitriles, ketones, alcohols, and N-methylpyrrolidone, dimethyl sulfoxide, dimethylformamide and dimethylacetamide.
- the reaction is particularly preferably carried out without a solvent or in chlorobenzene, xylene, dimethyl sulfoxide, N-methylpyrrolidone. It is also possible to use mixtures of the solvents mentioned.
- Suitable bases are generally inorganic compounds, such as alkali metal and alkaline earth metal hydroxides, alkali metal and alkaline earth metal oxides, alkali metal and alkaline earth metal hydrides, alkali metal amides, alkali metal and alkaline earth metal carbonates and alkali metal hydrogencarbonates, organometallic compounds, in particular alkali metal alkyls, alkyl magnesium halides, and alkali metal and alkaline earth metal alkoxides and dimethoxy magnesium.
- organometallic compounds in particular alkali metal alkyls, alkyl magnesium halides, and alkali metal and alkaline earth metal alkoxides and dimethoxy magnesium.
- organic bases eg tertiary amines such as trimethylamine, triethylamine, tri-isopropylamine, tributylamine and N-methylpiperidine, N-methylmorpholine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethyl-aminopyridine and bicyclic amines into consideration.
- tertiary amines such as tri-isopropylamine, tributylamine, N-methylmorpholine or N-methylpiperidine.
- the bases are generally used in catalytic amounts, but they can also be used equimolar, in excess or optionally as a solvent.
- the starting materials are generally reacted with one another in equimolar amounts. It may be advantageous for the yield to use the base and the malonate III in an excess based on the triazole.
- Phenylmalonates of the formula III are advantageously obtained from the reaction of correspondingly substituted bromobenzenes with dialkylmalonates under Cu (I) catalysis [cf. Chemistry Letters, pp. 367-370, 1981; EP-A 10 02788].
- the dihydroxytriazolopyrimidines of the formula IV are converted under the conditions known from WO-A 94/20501 into the dihalopyrimidines of the formula V in which Y is a halogen atom, preferably a bromine or a chlorine atom, in particular a chlorine atom.
- the halogenating agent [HAL] used is advantageously a chlorinating agent or a brominating agent such as phosphorus oxybromide or phosphorus oxychloride, optionally in the presence of a solvent.
- This reaction is usually carried out at 0 ° C to 150 ° C, preferably at 80 ° C to 125 ° C, performed [see. EP-A 770 615].
- This reaction is advantageously carried out at 0 ° C to 70 ° C, preferably 10 ° C to 35 ° C, preferably in the presence of an inert solvent such as ethers, eg. As dioxane, diethyl ether or especially tetrahydrofuran, halogenated hydrocarbons such as dichloromethane and aromatic hydrocarbons such as toluene [cp. WO-A 98/46608].
- ethers eg. As dioxane, diethyl ether or especially tetrahydrofuran, halogenated hydrocarbons such as dichloromethane and aromatic hydrocarbons such as toluene [cp. WO-A 98/46608].
- a base such as tertiary amines, for example triethylamine or inorganic bases, such as potassium carbonate is preferred; Excess amine of the formula VI can also serve as a base.
- the reaction temperature is usually 0 to 120.degree. C., preferably 10 to 40.degree. C. [cf. J. Heterocycl. Chem., Vol. 12, pp. 861-863 (1975)].
- Suitable solvents include ethers, such as dioxane, diethyl ether and, preferably, tetrahydrofuran, alcohols, such as methanol or ethanol, halogenated hydrocarbons, such as dichloromethane, and aromatic hydrocarbons, such as toluene or acetonitrile.
- ethers such as dioxane, diethyl ether and, preferably, tetrahydrofuran
- alcohols such as methanol or ethanol
- halogenated hydrocarbons such as dichloromethane
- aromatic hydrocarbons such as toluene or acetonitrile.
- the 5-alkyl-7-hydroxy-6-phenyltriazolopyrimidines IVa are obtained.
- X 1 is CC 4 -alkyl or C 1 -C 4 -haloalkyl.
- the 5-methyl-7-hydroxy-6-phenyltriazolopyrimidines are obtained [see. Chem. Pharm. Bull., 9, 801, (1961)].
- the preparation of the starting compounds IIIa is advantageously carried out under the conditions described in EP-A 10 02 788.
- the 5-alkyl-7-hydroxy-6-phenyltriazolopyrimidines thus obtained are reacted with halogenating agents [HAL] under the conditions described above to give the 7-halotriazolopyrimidines of the formula Va in which Y represents a halogen atom.
- halogenating agents such as phosphorus oxybromide, phosphorus oxychloride, thionyl chloride, thionyl bromide or sulfuryl chloride.
- the reaction may be carried out neat or in the presence of a solvent. Typical reaction temperatures are from 0 to 150 ° C or preferably from 80 to 125 ° C.
- compounds of the formula I in which X is C 4 -alkyl may alternatively be prepared from compounds I in which X is halogen, in particular chlorine, and malonates of the formula VIII are prepared.
- the subsequent saponification of the ester IX is carried out under generally customary conditions, depending on the various structural elements, the alkaline or acidic saponification of the compounds IX may be advantageous. Under the conditions of the ester saponification, the decarboxylation to I can already take place completely or partially.
- the decarboxylation is usually carried out at temperatures of 20 ° C to 180 ° C, preferably 50 ° C to 120 ° C, in an inert solvent, optionally in the presence of an acid.
- Suitable acids are hydrochloric acid, sulfuric acid, phosphoric acid, formic acid, acetic acid, p-toluenesulfonic acid.
- Suitable solvents are water, aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert.
- M is a valence Y metal ion, such as B, Zn or Sn, and X "is C 1 -C 3 alkyl, for example, by the following methods: J. Chem. Soc., Perkin Trans., 1, 1187 (1994), ibid. 1, 2345 (1996); WO-A 99/41255; Aust. J. Chem., Vol. 43, 733 (1990); J. Org. Chem., Vol. 43, 358 (1978); Chem. Soc. Chem. Commun., 866 (1979); Tetrahedron Lett, Vol. 34, 8267 (1993); ibid., Vol. 33, 413 (1992).
- the reaction mixtures are worked up in conventional, e.g. by mixing with water, separation of the phases and optionally chromatographic purification of the crude products.
- the intermediate and end products are z.T. in the form of colorless or pale brownish, viscous oils, which are freed or purified under reduced pressure and at moderately elevated temperature from volatile constituents. If the intermediate and end products are obtained as solids, the purification can also be carried out by recrystallization or trituration.
- Halogen fluorine, chlorine, bromine and iodine
- Alkyl saturated, straight-chain or branched hydrocarbon radicals having 1 to 4, 6 or 8 carbon atoms, for example CC 6 -alkyl, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methyl-propyl, 2-methylpropyl, 1,1- Dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2- Methyl pentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethyl butylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl
- Haloalkyl straight-chain or branched alkyl groups having 1 to 2, 4 or 6 carbon atoms (as mentioned above), wherein in these groups partially or completely the hydrogen atoms may be replaced by halogen atoms as mentioned above: in particular CC 2 -haloalkyl such as chloromethyl, bromomethyl , Dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 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-trichloroeth
- Alkenyl unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 4, 6 or 8 carbon atoms and one or two double bonds in any position, for example C 2 -C 6 alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl , 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2 Pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2 -butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl
- Haloalkenyl unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 8 carbon atoms and one or two double bonds in any position (as mentioned above), wherein in these groups, the hydrogen atoms partially or completely replaced by halogen atoms as mentioned above, in particular fluorine, chlorine and bromine could be;
- Alkynyl straight-chain or branched hydrocarbon groups having 2 to 4, 6 or 8 carbon atoms and one or two triple bonds in any position, for example C 2 -C 6 alkynyl such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl , 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2 Methyl 3-butynyl,
- Cycloalkyl mono- or bicyclic, saturated hydrocarbon groups having 3 to 6 or 8 carbon ring members, for example C 3 -C 8 -cycloalkyl, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl; 5- to 10-membered saturated, partially unsaturated or aromatic heterocycle containing one to four heteroatoms from the group O, N or S: - 5- or 6-membered heterocyclyl containing one to three nitrogen atoms and / or an oxygen or sulfur atom or a or two oxygen and / or sulfur atoms, for example 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isox
- 5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom 5-membered heteroaryl groups which contain, in addition to carbon atoms, one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom as ring members may, for example, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5 Oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, and 1,3,4-triazol-2-yl; 6-membered heteroaryl containing one to three or one to four nitrogen atoms: 6-membered ring heteroaryl groups which, in addition to carbon atoms, may contain one to three or one to four nitrogen atoms as
- Alkylene divalent linear chains of 3 to 5 CH 2 groups, eg CH 2 , CH 2 CH 2 , CH 2 CH 2 CH 2 , CH 2 CH 2 CH 2 CH 2 and CH 2 CH 2 CH 2 CH 2 CH 2 ;
- Oxyalkylene divalent unbranched chains of 2 to 4 CH 2 groups, wherein a valence is bonded to the skeleton via an oxygen atom, for example OCH 2 CH 2 , OCH 2 CH 2 CH 2 and OCH 2 CH 2 CH 2 CH 2 ;
- Oxyalkylenoxy divalent unbranched chains of 1 to 3 CH 2 groups, both valences being bonded to the skeleton via an oxygen atom, eg OCH 2 O, OCH 2 CH 2 O and OCH 2 CH 2 CH 2 O;
- R 1 is dd-alkyl, C 2 -C 6 -alkenyl or CC 8 -haloalkyl.
- R 1 is a group A: FF (CH '2,)' q-CHR 3 - AZ 'Z wherein
- Z 1 is hydrogen, fluorine or C 1 -C 6 -fluoroalkyl
- Z 2 is hydrogen or fluorine, or Z and Z 2 together form a double bond
- q is 0 or 1
- R 3 is hydrogen or methyl
- R 1 is C 3 -C 6 -cycloalkyl, which may be substituted by CC 4 alkyl.
- R 1 and / or R 2 contain haloalkyl or haloalkenyl groups with chiral centers, the (S) - isomers are preferred for these groups. In the case of halogen-free alkyl or alkenyl groups with chiral centers in R 1 or R 2 , the (R) -configured isomers are preferred.
- R 1 and R 2 together with the nitrogen atom to which they are attached form a piperidinyl, morpholinyl or thio morpholinyl, in particular a piperidinyl ring which is optionally substituted by one to three halogen, dC 4 -alkyl or dC 4 -haloalkyl.
- Particularly preferred are the compounds in which R 1 and R 2 together with the nitrogen atom to which they are attached form a 4-methylpiperidine ring.
- a further preferred subject of the invention are compounds I in which R and R 2 together with the nitrogen atom to which they are attached form a pyrazole ring which is optionally substituted by one or two groups halogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkyl.
- Haloalkyl in particular by 3,5-dimethyl or 3,5-di- (trifluoromethyl) is substituted.
- R 2 is hydrogen or methyl; or R 1 and R 2 together are - (CH 2 ) 2 CH (CH 3 ) (CH 2 ) 2-, - (CH 2 ) 2 CH (CF 3 ) (CH 2 ) 2 - or - (CH 2 ) 2 O (CH2) 2 - mean.
- X is halogen, CC-alkyl, cyano or C 1 -C 4 -alkoxy, such as chlorine, methyl, cyano, methoxy or ethoxy, especially chlorine or methyl, in particular chlorine.
- shark is in particular chlorine or fluorine.
- compounds I are preferred in which L 1 is C 2 -alkoxy, such as methoxy; cyano; Halomethyl, such as trifluoromethyl or dd-alkoxycarbonyl, such as methoxycarbonyl means.
- L 2 and L 3 particularly preferably mean hydrogen.
- L 2 CC 2 alkoxy such as methoxy
- cyano such as cyano
- Halomethyl such as trifluoromethyl or dC 4 alkoxycarbonyl, such as methoxycarbonyl.
- L 1 and L 3 are hydrogen.
- a preferred embodiment of the invention relates to compounds of the formula 1.1:
- GC 2 -C 6 -alkyl in particular ethyl, n- and i-propyl, n-, sec-, tert-butyl, and CC 4 -alkoxymethyl, in particular ethoxymethyl, or C 3 -C 6 -cycloalkyl, in particular cyclopentyl or cyclohexyl ;
- R 2 is hydrogen or methyl;
- X is chlorine, methyl, cyano, methoxy or ethoxy.
- a further preferred embodiment of the invention relates to compounds in which R 1 and R 2 together with the nitrogen atom to which they are attached form a five- or six-membered heterocyclyl or heteroaryl which is bonded via N and another heteroatom from the group O , N and S as a ring member and / or one or more substituents selected from the group halogen, CC 6 alkyl, d-Ce-haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 haloalkenyl, dC 6 alkoxy CRCE haloalkoxy C_-C 6 alkenyloxy, C 3 -C 6 haloalkenyloxy, -C 6 alkylene and oxy-dC 3, - may bear alkyleneoxy.
- These compounds correspond in particular to formula I.2,
- D together with the nitrogen atom forms a five- or six-membered heterocyclyl or heteroaryl which is bonded via N and contains a further heteroatom from the group O, N and S as ring member and / or one or more substituents from the group halogen, dC 4 - Alkyl, CC 4 alkoxy and dC 2 haloalkyl; and
- X is chlorine, methyl, cyano, methoxy or ethoxy.
- Another preferred embodiment of the invention relates to compounds of the formula I.3.
- Y is hydrogen or C 1 -C 4 -alkyl, in particular methyl and ethyl, and X is chlorine, methyl, cyano, methoxy or ethoxy.
- Table 84 Compounds of the formula I in which X is methoxy, Hal fluorine, L 1 and L 2 are hydrogen, L 3 is methoxycarbonyl and the combination of R 1 and R 2 for a compound corresponds in each case to one row of Table A.
- Table 85 Compounds of the formula I in which X is chlorine, Hal chlorine, L 1 and L 2 are hydrogen, L 3 is fluorine and the combination of R 1 and R 2 for a compound corresponds in each case to one row of Table A.
- Table 86 Compounds of the formula I in which X is cyano, Hal is chlorine, L 1 and L 2 are hydrogen, L 3 is fluorine and the combination of R 1 and R 2 for a compound corresponds in each case to one row of Table A.
- Table 87 Compounds of the formula I in which X is methyl, Hal is chlorine, L 1 and L 2 are hydrogen, L 3 is fluorine and the combination of R 1 and R 2 for each compound corresponds to one row of Table A.
- Table 88 Compounds of the formula I in which X is methoxy, Hal is chlorine, L 1 and L 2 are hydrogen, L 3 is fluorine and the combination of R 1 and R 2 for a compound corresponds in each case to one row of Table A.
- Table 90 Compounds of the formula I in which X is cyano, Hal is chlorine, L 1 and L 2 are hydrogen, L 3 is chlorine and the combination of R 1 and R 2 for a compound corresponds in each case to one row of Table A.
- Table 91 Compounds of the formula I in which X is cyano, Hal is chlorine, L 1 and L 2 are hydrogen, L 3 is chlorine and the combination of R 1 and R 2 for a compound corresponds in each case to one row of Table A.
- Table 107 Compounds of the formula I in which X is methyl, Hal fluorine, L 1 cyano, L 2 is hydrogen, L 3 is fluorine and the combination of R 1 and R 2 for a compound corresponds in each case to one row of Table A.
- Table 108 Compounds of the formula I in which X is methoxy, Hal fluorine, L 1 cyano, L 2 is hydrogen, L 3 is fluorine and the combination of R 1 and R 2 for a compound corresponds in each case to one row of Table A.
- Table 109 Compounds of the formula I in which X is chlorine, Hal fluorine, L 1 cyano, L 2 is hydrogen, L 3 is chlorine and the combination of R 1 and R 2 for a compound corresponds in each case to one row of Table A.
- Table 110 Compounds of the formula I in which X is cyano, Hal fluorine, L 1 cyano, L 2 is hydrogen, L 3 is chlorine and the combination of R 1 and R 2 for a compound corresponds in each case to one row of Table A.
- Table 112 Compounds of the formula I in which X is methoxy, Hal fluorine, L 1 cyano, L z is hydrogen, L 3 is chlorine and the combination of R 1 and R 2 for a compound corresponds in each case to one row of Table A.
- Table 113 Compounds of the formula I in which X is chlorine, Hal fluorine, L 1 cyano, L 2 is hydrogen, L 3 is cyano and the combination of R 1 and R 2 for each compound corresponds to one row of Table A.
- Table 114 Compounds of the formula I in which X is chlorine, Hal fluorine, L 1 cyano, L 2 is hydrogen, L 3 is cyano and the combination of R 1 and R 2 for each compound corresponds to one row of Table A.
- Table 130 Compounds of the formula I in which X is cyano, Hal is chlorine, L 1 is cyano, L 2 is hydrogen, L 3 is chlorine and the combination of R 1 and R 2 for each compound corresponds to one row of Table A.
- Table 131 Compounds of the formula I in which X is methyl, Hal is chlorine, L 1 is cyano, L 2 is hydrogen, L 3 is chlorine and the combination of R 1 and R 2 for each compound corresponds to one row of Table A.
- Table 132 Compounds of the formula I in which X is methoxy, Hal is chlorine, L 1 is cyano, L 2 is hydrogen, L 3 is chlorine and the combination of R 1 and R 2 for a compound corresponds in each case to one row of Table A.
- Table 133 Compounds of the formula I in which X is chlorine, Hal chlorine, L 1 cyano, L 2 is hydrogen, L 3 is cyano and the combination of R 1 and R 2 for a compound corresponds in each case to one row of Table A.
- Table 134 Compounds of the formula I in which X is cyano, Hal is chlorine, L 1 is cyano, L 2 is hydrogen, L 3 is cyano and the combination of R 1 and R 2 for a compound corresponds in each case to one row of Table A.
- Table 135 Compounds of the formula I in which X is methyl, Hal is chlorine, L 1 is cyano, L 2 is hydrogen, L 3 is cyano and the combination of R 1 and R 2 for each compound corresponds to one row of Table A.
- Table 136 Compounds of the formula I in which X is methoxy, Hal is chlorine, L 1 is cyano, L 2 is hydrogen, L 3 is cyano and the combination of R 1 and R 2 for each compound corresponds to one row of Table A.
- Table 137 Compounds of the formula I in which X is methoxy, Hal is chlorine, L 1 is cyano, L 2 is hydrogen, L 3 is cyano and the combination of R 1 and R 2 for each compound corresponds to one row of Table A.
- Table 153 Compounds of the formula I in which X corresponds to chlorine, Hal fluorine, L 1 methoxy, L 2 hydrogen, L 3 cyano and the combination of R and R 2 for a compound corresponds in each case to one row of Table A.
- Table 154 Compounds of the formula I in which X is cyano, Hal fluorine, L 1 methoxy, L 2 is hydrogen, L 3 is cyano and the combination of R 1 and R 2 for a compound corresponds in each case to one row of Table A.
- Table 155 Compounds of the formula I in which X is methyl, Hal fluorine, L 1 methoxy, L 2 is hydrogen, L 3 is cyano and the combination of R 1 and R 2 for a compound corresponds in each case to one row of Table A.
- Table 156 Compounds of the formula I in which X is methoxy, Hal fluorine, L 1 methoxy, L 2 is hydrogen, L 3 is cyano and the combination of R 1 and R 2 for a compound corresponds in each case to one row of Table A.
- Table 157 Compounds of the formula I in which X is chlorine, Hal fluorine, L 1 methoxy, L 2 is hydrogen, L 3 is methoxy and the combination of R 1 and R 2 for each compound corresponds to one row of Table A.
- Table 158 Compounds of the formula I in which X is cyano, Hal fluorine, L 1 methoxy, L 2 is hydrogen, L 3 is methoxy and the combination of R 1 and R 2 for a compound corresponds in each case to one row of Table A.
- Table 159 Compounds of the formula I in which X is methyl, Hal fluorine, L 1 methoxy, L 2 is hydrogen, L 3 is methoxy and the combination of R and R 2 for a compound corresponds in each case to one row of Table A.
- Table 160 Compounds of the formula I in which X is methyl, Hal fluorine, L 1 methoxy, L 2 is hydrogen, L 3 is methoxy and the combination of R and R 2 for a compound corresponds in each case to one row of Table A.
- Table 176 Compounds of the formula I in which X is methoxy, Hal is chlorine, L 1 is methoxy, L 2 is hydrogen, L 3 is cyano and the combination of R 1 and R 2 for a compound corresponds in each case to one row of Table A.
- Table 177 Compounds of the formula I in which X is chlorine, Hal is chlorine, L is methoxy, L 2 is hydrogen, L 3 is methoxy and the combination of R 1 and R 2 for each compound corresponds to one row of Table A.
- Table 178 Compounds of the formula I in which X is cyano, Hal is chlorine, L 1 is methoxy, L 2 is hydrogen, L 3 is methoxy and the combination of R and R 2 for a compound corresponds in each case to one row of Table A.
- Table 180 Compounds of the formula I in which X is methoxy, Hal is chlorine, L 1 is methoxy, L 2 is hydrogen, L 3 is methoxy and the combination of R 1 and R 2 for each compound corresponds to one row of Table A.
- Table 181 Compounds of the formula I in which X is chlorine, Hal chlorine, L 1 methoxy, L 2 is hydrogen, L 3 is methoxycarbonyl and the combination of R 1 and R 2 for a compound corresponds in each case to one row of Table A.
- Table 182 Compounds of the formula I in which X is cyano, Hal is chlorine, L 1 is methoxy, L 2 is hydrogen, L 3 is methoxycarbonyl and the combination of R 1 and R 2 for each compound corresponds to one row of Table A.
- Table 183 Compounds of the formula I in which X is cyano, Hal is chlorine, L 1 is methoxy, L 2 is hydrogen, L 3 is methoxycarbonyl and the combination of R 1 and R 2 for each compound corresponds to one row of Table A.
- the compounds I are suitable as fungicides. They are distinguished by outstanding activity against a broad spectrum of phytopathogenic fungi, in particular from the classes of the Ascomycetes, Deuteromycetes, Oomycetes and Bassidiomycetes. They are in part systemically effective and can be used in crop protection as foliar and soil fungicides.
- the compounds I are also suitable for controlling harmful fungi such as Pecilomyces variotii in the protection of materials (for example wood, paper, paint dispersions, fibers or fabrics) and in the protection of stored products.
- harmful fungi such as Pecilomyces variotii in the protection of materials (for example wood, paper, paint dispersions, fibers or fabrics) and in the protection of stored products.
- the compounds I are used by treating the fungi or the plants, seeds, materials or the soil to be protected against fungal attack with a fungicidally effective amount of the active ingredients.
- the application can be done both before and after the infection of the materials, plants or seeds by the fungi.
- the fungicidal compositions generally contain between 0.1 and 95, preferably between 0.5 and 90 wt .-% of active ingredient.
- the application rates in the application in crop protection depending on the nature of the desired effect between 0.01 and 2.0 kg of active ingredient per ha.
- amounts of active ingredient of 1 to 1000 g / 100 kg of seed preferably 1 to 200 g / 100 kg, in particular 5 to 100 g / 100 kg are used.
- the application rate of active ingredient depends on the type of application and the desired effect. Usual application rates are, for example, 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active ingredient per cubic meter of material treated in the material protection.
- the compounds I can be converted into the usual formulations, e.g. Solutions, emulsions, suspensions, dusts, powders, pastes and granules.
- the application form depends on the respective purpose; It should in any case ensure a fine and uniform distribution of the compound according to the invention.
- the formulations are prepared in a known manner, e.g. by stretching the active ingredient with solvents and / or carriers, if desired using emulsifiers and dispersants.
- Suitable solvents / auxiliaries are essentially: water, aromatic solvents (eg Solvesso products, xylene), paraffins (eg petroleum fractions), alcohols (eg methanol, butanol, pentanol, benzyl alcohol), ketones (eg cyclohexanone, gamma Butyrolactone), pyrrolidones (NMP, NOP), acetates (glycol diacetate), glycols, dimethyl fatty acid amides, fatty acids and fatty acid esters.
- aromatic solvents eg Solvesso products, xylene
- paraffins eg petroleum fractions
- alcohols eg methanol, butanol, pentanol, benzyl alcohol
- ketones eg cyclohe
- solvent mixtures may also be used, - carriers such as ground natural minerals (for example kaolins, clays, talc, chalk) and ground synthetic minerals (for example finely divided silica, silicates); Emulsifiers, such as nonionic and anionic emulsifiers (for example, polyoxyethylene fatty alcohol ethers, alkyl sulfonates and arylsulfonates) and dispersants, such as lignin-sulphite liquors and methylcellulose.
- ground natural minerals for example kaolins, clays, talc, chalk
- ground synthetic minerals for example finely divided silica, silicates
- Emulsifiers such as nonionic and anionic emulsifiers (for example, polyoxyethylene fatty alcohol ethers, alkyl sulfonates and arylsulfonates)
- dispersants such as lignin-sulphite liquors and methylcellulose.
- the surface-active substances used are alkali metal, alkaline earth metal, ammonium salts of lignin sulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid, alkylarylsulfonates, alkyl sulfates, alkyl sulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, and condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde , Condensation products of naphthalene or naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene lenoctylphenolether, ethoxylated isooctylphenol, octylphenol, nonylphenol, Alkylphe- nolpolyglykolet er, Tributyl
- mineral oil fractions of medium to high boiling point such as kerosine or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, strong polar solvents, e.g. Dimethylsulfoxide, N-methylpyrrolidone or water into consideration.
- mineral oil fractions of medium to high boiling point such as kerosine or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivative
- Powders, dispersants and dusts may be prepared by mixing or co-grinding the active substances with a solid carrier.
- Granules e.g. Coated, impregnated and homogeneous granules can be prepared by binding the active compounds to solid carriers.
- Solid carriers are e.g. Mineral earths, such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulphate, magnesium oxide, ground plastics, fertilizers, e.g. Ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder and other solid carriers.
- Mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulphate, magnesium oxide, ground plastics
- the formulations generally contain between 0.01 and 95% by weight, preferably between 0.1 and 90% by weight of the active ingredient.
- the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum).
- formulations are: 1. Products for dilution in water
- a compound of the invention 10 parts by weight of a compound of the invention are dissolved in water or a water-soluble solvent. Alternatively, wetting agents or other adjuvants are added. When diluted in water, the active ingredient dissolves.
- a compound according to the invention 40 parts by weight of a compound according to the invention are dissolved in xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5%).
- This mixture is introduced by means of an emulsifier (Ultraturax) in water and brought to a homogeneous emulsion. Dilution in water results in an emulsion.
- Agitator ball mill to a fine suspension of active ingredient crushed. Dilution in water results in a stable suspension of the active ingredient.
- Water-dispersible and Water-soluble Granules 50 parts by weight of a compound according to the invention are finely ground with the addition of dispersants and wetting agents and prepared by means of industrial equipment (for example extrusion, spray tower, fluidized bed) as water-dispersible or water-soluble granules. Dilution in water results in a stable dispersion or solution of the active ingredient.
- WP, SP Water-dispersible and Water-Soluble Powders (WP, SP) 75 parts by weight of a compound according to the invention are ground in a rotor-stator mill with the addition of dispersants and wetting agents and silica gel. Dilution in water results in a stable dispersion or solution of the active substance.
- H dusts (DP) 5 parts by weight of a compound according to the invention are finely ground and intimately mixed with 95% finely divided kaolin. This gives a dust.
- a compound according to the invention 0.5 parts by weight of a compound according to the invention are finely ground and combined with 95.5% excipients. Common methods are the extrusion, the Spray drying or the fluidized bed. This gives granules for direct application.
- ULV solutions 10 parts by weight of a compound of the invention are dissolved in an organic solvent e.g. Xylene dissolved. This gives you a product for direct application.
- organic solvent e.g. Xylene dissolved.
- the active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, e.g. in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, litter, granules by spraying, misting, dusting, scattering or pouring.
- the forms of application depend entirely on the intended use; In any case, they should ensure as far as possible the finest distribution of the active compounds according to the invention.
- Aqueous application forms can be prepared from emulsion concentrates, pastes or wettable powders (wettable powders, oil dispersions) by adding water.
- the substances as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetter, tackifier, dispersant or emulgent. But it can also be made of effective substance wetting, adhesion, dispersing or emulsifying and possibly solvent or oil concentrates, which are suitable for dilution with water.
- the active compound concentrations in the ready-to-use preparations can be varied within wide ranges. In general, they are between 0.0001 and 10%, preferably between 0.01 and 1%.
- the active ingredients can also be used with great success in the ultra-low-volume (ULV) process, it being possible to apply formulations containing more than 95% by weight of active ingredient or even the active ingredient without additives.
- UUV ultra-low-volume
- wetting agents for example with herbicides, insecticides, growth regulators, fungicides or else with fertilizers.
- fertilizers When mixing the compounds I or the agents containing them in the application form as fungicides with other fungicides is obtained in many cases, an enlargement of the fungicidal spectrum of activity.
- Acylalanines such as benalaxyl, metalaxyl, ofurace, oxadixyl;
- Amine derivatives such as aldimorph, dodine, dodemorph, fenpropimorph, fenpropidin, guazatine, iminoctadine, spiroxamine, tridemorph;
- Anilinopyrimidines such as pyrimethanil, mepanipyrim or cyrodinyl;
- antibiotics such as cycloheximide, griseofulvin, kasugamycin, natamycin, polyoxin or streptomycin;
- Azoles such as bitertanol, bromoconazole, cyproconazole, difenoconazole, dinitroconazole, enilconazole, epoxiconazole, fenbuconazole, fluquiconazole, flusilazole, flutriafol, hexaconazole, imazalil, metconazole, myclobutanil, penconazole, propiconazole, prochlorazole, prothioconazole, tebuconazole, triadimefon, triadimol, triflumizole , Triticonazole;
- Dicarboximides such as iprodione, myclozoline, procymidone, vinclozolin;
- Dithiocarbamates such as Ferbam, Nabam, Maneb, Mancozeb, Metam, Metiram, Propineb, Polycarbamate, Thiram, Ziram, Zineb;
- Heterocyclic compounds such as anilazine, benomyl, boscalid, carbendazim, carboxaldine, oxycarboxine, cyazofamide, dazomet, dithianone, famoxadone, fenamidone, fenarimol, fuberidazole, flutolanil, furametpyr, isoprothiolane, mepronil, nuarimol, probenazole, proquinazide, pyrifenox, pyroquilone, Quinoxyfen, silthiofam, thiabenazole, thifluzamide, thiophanate-methyl, tiadinil, tricyclazole, triforine;
- Copper fungicides such as Bordeaux broth, copper acetate, copper oxychloride, basic copper sulfate;
- Nitrophenyl derivatives such as binapacryl, dinocap, dinobutone, nitrophthalic-isopropyl;
- Phenylpyrroles such as fenpiclonil or fludioxonil; • sulfur;
- fungicides such as acibenzolar-S-methyl, benthiavalicarb, carpropamide, chlorotrilone, cyflufenamid, cymoxanil, dazomet, diclomethine, diclocymet, diethofencarb, edifenphos, ethaboxam, fenhexamide, fentin acetate, fenoxanil, ferimzone, fluazinam, fosetyl, Fosetyl-aluminum, iprovalicarb, hexachlorobenzene, metrafenone, pencycuron, propamocarb, phthalide, toloclofos-methyl, quintozene, zoxamide; Strobilurins such as azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin, pyr
- Sulfenic acid derivatives such as captafol, captan, dichlofluanid, folpet, tolylfluanid;
- Cinnamic acid amides and analogues such as dimethomorph, flumetover or flumorph.
- the aqueous phase was extracted with methylene chloride, the aqueous phase was filtered off, the filter residue was dissolved in tetrahydrofuran. Both the combined organic phases were dried and freed from the solvents. The residue obtained was 2.0 g of the title compound as a beige solid, which was used without further purification in the next reaction.
- the active compounds were separately prepared as a stock solution with 25 mg of active ingredient, which with a mixture of acetone and / or D SO and the emulsifier Uniperol® EL (wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) in the volume ratio solvent Emulsifier from 99 to 1 ad 10 ml was filled. It was then made up to 100 ml with water. This stock solution was diluted with the described solvent-emulsifier-water mixture to the drug concentration given below.
- Uniperol® EL wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols
- Paprika seedlings of the cultivar "Neusiedler Ideal Elite” were sprayed to drip point with an aqueous suspension in the concentration of active compound stated below, after 2-3 leaves had developed well.
- the treated plants were inoculated with a spore suspension of Botrytis cinerea containing 1.7 ⁇ 10 6 spores / ml in a 2% aqueous biomalt solution.
- the test plants were placed in a climatic chamber at 22 to 24 ° C, darkness and high humidity. After 5 days, the extent of fungal attack on the leaves could be determined visually in%.
- Leaves of potted plants of the "Golden Queen" variety were sprayed to drip point with an aqueous suspension in the concentration of active compound specified below. The following day, the leaves were infected with an aqueous spore suspension of Alternana solani in 2% biomalt solution with a density of 0.17 x 10 6 spores / ml. Subsequently, the plants were placed in a water vapor-saturated chamber at temperatures between 20 and 22 ° C. After 5 days the disease had started The untreated but infected control plants developed so strongly that the infestation could be determined visually in%.
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- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10360047 | 2003-12-18 | ||
DE102004019458 | 2004-04-19 | ||
PCT/EP2004/014328 WO2005058907A1 (fr) | 2003-12-18 | 2004-12-16 | 6-(2-halogenophenyl)-triazolopyrimidines, procede pour leur production et leur utilisation pour lutter contre des champignons nuisibles, ainsi qu'agents les contenant |
Publications (1)
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EP1697367A1 true EP1697367A1 (fr) | 2006-09-06 |
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EP04803941A Withdrawn EP1697367A1 (fr) | 2003-12-18 | 2004-12-16 | 6-(2-halogenophenyl)-triazolopyrimidines, procede pour leur production et leur utilisation pour lutter contre des champignons nuisibles, ainsi qu'agents les contenant |
Country Status (15)
Country | Link |
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US (1) | US20070078149A1 (fr) |
EP (1) | EP1697367A1 (fr) |
JP (1) | JP2007514689A (fr) |
KR (1) | KR20060124641A (fr) |
AR (1) | AR046961A1 (fr) |
AU (1) | AU2004299258A1 (fr) |
BR (1) | BRPI0417740A (fr) |
CA (1) | CA2549169A1 (fr) |
CO (1) | CO5690646A2 (fr) |
CR (1) | CR8470A (fr) |
EA (1) | EA200601108A1 (fr) |
IL (1) | IL175395A0 (fr) |
PE (1) | PE20050813A1 (fr) |
TW (1) | TW200528457A (fr) |
WO (1) | WO2005058907A1 (fr) |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
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US5593996A (en) * | 1991-12-30 | 1997-01-14 | American Cyanamid Company | Triazolopyrimidine derivatives |
TW224044B (fr) * | 1991-12-30 | 1994-05-21 | Shell Internat Res Schappej B V | |
DE10063115A1 (de) * | 2000-12-18 | 2002-06-27 | Bayer Ag | Triazolopyrimidine |
EP1616870A1 (fr) * | 2001-07-05 | 2006-01-18 | Basf Aktiengesellschaft | Triazolopyrimidines fongicides, procédé pour leur preparation, leur usage pour combattre les champignons et agents les contenant |
KR20040105772A (ko) * | 2002-03-21 | 2004-12-16 | 바스프 악티엔게젤샤프트 | 살진균성 트리아졸로피리미딘, 이의 제조방법 및 유해진균 방제를 위한 이의 용도 및 상기 성분을 함유하는조성물 |
DE10218592A1 (de) * | 2002-04-26 | 2003-11-06 | Bayer Cropscience Ag | Triazolopyrimidine |
US7196106B2 (en) * | 2002-11-05 | 2007-03-27 | Merck & Co., Inc | Cyanothiophene derivatives, compositions containing such compounds and methods of use |
UA80304C2 (en) * | 2002-11-07 | 2007-09-10 | Basf Ag | Substituted 6-(2-halogenphenyl)triazolopyrimidines |
-
2004
- 2004-12-16 BR BRPI0417740-1A patent/BRPI0417740A/pt not_active IP Right Cessation
- 2004-12-16 AU AU2004299258A patent/AU2004299258A1/en not_active Abandoned
- 2004-12-16 US US10/580,416 patent/US20070078149A1/en not_active Abandoned
- 2004-12-16 EP EP04803941A patent/EP1697367A1/fr not_active Withdrawn
- 2004-12-16 CA CA002549169A patent/CA2549169A1/fr not_active Abandoned
- 2004-12-16 KR KR1020067011884A patent/KR20060124641A/ko not_active Withdrawn
- 2004-12-16 EA EA200601108A patent/EA200601108A1/ru unknown
- 2004-12-16 WO PCT/EP2004/014328 patent/WO2005058907A1/fr active Application Filing
- 2004-12-16 JP JP2006544335A patent/JP2007514689A/ja not_active Withdrawn
- 2004-12-17 AR ARP040104764A patent/AR046961A1/es unknown
- 2004-12-17 TW TW093139523A patent/TW200528457A/zh unknown
-
2005
- 2005-01-03 PE PE2005000009A patent/PE20050813A1/es not_active Application Discontinuation
-
2006
- 2006-05-02 IL IL175395A patent/IL175395A0/en unknown
- 2006-06-16 CO CO06059316A patent/CO5690646A2/es not_active Application Discontinuation
- 2006-06-21 CR CR8470A patent/CR8470A/es not_active Application Discontinuation
Non-Patent Citations (1)
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See references of WO2005058907A1 * |
Also Published As
Publication number | Publication date |
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KR20060124641A (ko) | 2006-12-05 |
CO5690646A2 (es) | 2006-10-31 |
AU2004299258A1 (en) | 2005-06-30 |
US20070078149A1 (en) | 2007-04-05 |
EA200601108A1 (ru) | 2006-12-29 |
TW200528457A (en) | 2005-09-01 |
CA2549169A1 (fr) | 2005-06-30 |
JP2007514689A (ja) | 2007-06-07 |
IL175395A0 (en) | 2006-09-05 |
AR046961A1 (es) | 2006-01-04 |
BRPI0417740A (pt) | 2007-04-03 |
WO2005058907A1 (fr) | 2005-06-30 |
CR8470A (es) | 2006-12-07 |
PE20050813A1 (es) | 2005-11-04 |
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