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WO2003010145A1 - 4-hydroxy-quinolones substituees par biphenyle et leur utilisation comme pesticides et herbicides - Google Patents

4-hydroxy-quinolones substituees par biphenyle et leur utilisation comme pesticides et herbicides Download PDF

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Publication number
WO2003010145A1
WO2003010145A1 PCT/EP2002/007570 EP0207570W WO03010145A1 WO 2003010145 A1 WO2003010145 A1 WO 2003010145A1 EP 0207570 W EP0207570 W EP 0207570W WO 03010145 A1 WO03010145 A1 WO 03010145A1
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WO
WIPO (PCT)
Prior art keywords
alkyl
alkoxy
chlorine
fluorine
formula
Prior art date
Application number
PCT/EP2002/007570
Other languages
German (de)
English (en)
Inventor
Reiner Fischer
Astrid Ullmann
Karl-Heinz Kuck
Stefan Hillebrand
Axel Trautwein
Jörg KONZE
Ulrike Wachendorff-Neumann
Astrid Mauler-Machnik
Christoph Erdelen
Original Assignee
Bayer Cropscience Ag
Lubos-Erdelen, Angelika
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Bayer Cropscience Ag, Lubos-Erdelen, Angelika filed Critical Bayer Cropscience Ag
Priority to BR0211343-0A priority Critical patent/BR0211343A/pt
Priority to MXPA04000579A priority patent/MXPA04000579A/es
Priority to EP02754845A priority patent/EP1412333A1/fr
Priority to KR10-2003-7017189A priority patent/KR20040031710A/ko
Priority to JP2003515504A priority patent/JP2005500339A/ja
Publication of WO2003010145A1 publication Critical patent/WO2003010145A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • 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
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/53—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
    • C07C233/55—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a carbon atom of an unsaturated carbon skeleton
    • 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
    • C07D401/12—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 linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to new biphenyl-substituted 4-hydroxy-quinolones, several processes for their preparation and their use as pesticides, microbicides and herbicides.
  • W represents hydrogen, alkyl, halogen, haloalkyl or alkoxy
  • X represents halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyano
  • Y stands for optionally substituted aryl or hetaryl
  • Z represents hydrogen, halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or
  • n stands for the numbers 0-2
  • E represents a metal ion or an ammonium ion
  • M oxygen or sulfur
  • R.1 represents alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl or cycloalkyl optionally substituted by halogen, alkyl or alkoxy, in which one or more methylene groups can be replaced by heteroatoms, each optionally substituted phenyl,
  • Phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl, R2 represents alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl, which is optionally substituted by halogen, or cycloalkyl, phenyl or benzyl which is optionally substituted,
  • R ⁇ , R4 and R ⁇ independently of one another for each, if appropriate
  • R6 and R? independently of one another represent hydrogen, in each case optionally substituted by halogen, alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, optionally substituted phenyl, optionally substituted benzyl, or together with the N atom to which they are attached, for one optionally substituted by oxygen or sulfur interrupted ring.
  • the compounds of the formula (I) can be present in different compositions as geometric and / or optical isomers or isomer mixtures, which can optionally be separated in a customary manner. Both the pure isomers and the isomer mixtures, their preparation and use, and agents containing them are the subject of the present invention. For the sake of simplicity, however, the following always refers to compounds of the formula (I), although both the pure compounds and, if appropriate, mixtures with different proportions of isomeric compounds can be meant.
  • A, B, C, D, E, L, M, W, X, Y, Z, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 have the meanings given above.
  • A, B, C, D, W, X, Y and Z have the meanings given above, if
  • R 8 represents alkyl (preferably C 1 -C 6 -alkyl)
  • Rl has the meaning given above
  • R 2 and M have the meanings given above,
  • R 3 has the meaning given above
  • Me for a mono- or divalent metal preferably an alkali or alkaline earth metal such as lithium, sodium, potassium, magnesium or calcium
  • an alkali or alkaline earth metal such as lithium, sodium, potassium, magnesium or calcium
  • Ri i, R12 ? R13 independently of one another represent hydrogen or alkyl (preferably Ci-Cg-alkyl),
  • the compounds according to the invention are generally defined by the formula (I).
  • W preferably represents hydrogen, Cj-Cg alkyl, fluorine, chlorine, bromine, C ⁇ -C 4 haloalkyl or C j -C 6 - alkoxy,
  • X preferably represents fluorine, chlorine, bromine, CJ-C ⁇ -alkyl, Cj-C-i-haloalkyl, Cj-Cg-alkoxy, C ⁇ -C4-haloalkoxy or cyano,
  • Y preferably represents one of the radicals
  • V 1 preferably represents hydrogen, halogen, Cj-Cg alkoxy,
  • V 3 preferably represents hydrogen, fluorine, chlorine, methyl or methoxy
  • Z preferably represents hydrogen, fluorine, chlorine, bromine, Ci-Cg-alkyl, C j -C -
  • Haloalkyl Ci-Cg-alkoxy, C, -C 4 -haloalkoxy or cyano
  • A, B, C and D preferably each independently represent hydrogen, C r C 6 alkyl, fluorine, chlorine, bromine, iodine, C r C 6 alkoxy, C r C 4 haloalkyl,
  • Cj -C-C 4 haloalkoxy C j -C 4 alkyl-S (O) n -, cyano, nitro or for each optionally by Cj-C 4 - alkyl, fluorine, chlorine, bromine, Cj-C 4 alkoxy, C j - C2-haloalkyl, Cj-C2-haloalkoxy, cyano or nitro substituted phenyl, phenoxy or phenylthio,
  • n preferably represents the numbers 0-2,
  • G preferably represents hydrogen (a) or one of the groups
  • E represents a metal ion or an ammonium ion
  • M represents oxygen or sulfur
  • Rl preferably represents in each case optionally substituted by halogen C 1 -C 20 -alkyl, C 2 -C 2 o-alkenyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkylthio- C 1 -C 6 -alkyl, poly Cj-Cg-alkoxy-Ci-Cg-alkyl or optionally substituted by halogen, Ci-Cg-alkyl or Cj-Cg-alkoxy substituted Cß-Cg-cycloalkyl, in which one or more (preferably one or two) ring members not directly adjacent are replaced by oxygen and / or sulfur,
  • Ci-Cg-alkylsulfonyl substituted phenyl Ci-Cg-alkylsulfonyl substituted phenyl
  • phenyl-Ci-Cg-alkyl optionally substituted by halogen, nitro, cyano, Cj-Cg-alkyl, Ci-Cg-alkoxy, Ci-Cg-haloalkyl or Ci-Cg-haloalkoxy,
  • hetaryl optionally substituted by halogen, C 1 -C 6 -alkyl or trifluoromethyl (for example pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl),
  • phenoxy-Ci-Cg-alkyl optionally substituted by halogen or Ci-Cg-alkyl or
  • hetaryloxy-Ci-Cg-alkyl optionally substituted by halogen, amino or Cj-Cg-alkyl (for example pyridyloxy-Ci-Cg-alkyl, pyrimidyloxy-C j- Cg-alkyl or thiazolyloxy-C j - Coe-alkyl)
  • R 2 preferably represents in each case optionally substituted by halogen Ci - C 2 o-alkyl, C 2 -C 2 o-alkenyl, -C-C 8 alkoxy-C 2 -C 8 alkyl, poly-Ci -Cg-alk- oxy-C 2 -Cg-alkyl, for C3-Cg-cycloalkyl which is optionally substituted by halogen, Cj-Cg-alkyl or Ci-Cg-alkoxy or
  • Ci-Cg-alkyl for each optionally substituted by halogen, cyano, nitro, Ci-Cg-alkyl, Ci-Cg-alkoxy, Ci-Cg-haloalkyl or Ci-Cg-haloalkoxy
  • R 3 preferably represents Ci-Cg-alkyl optionally substituted by halogen or in each case optionally substituted by halogen, Ci-Cg-alkyl, Ci-Cg-alkoxy, Ci -C_ ⁇ .-haloalkyl, Ci-C4-haloalkoxy, cyano or nitro
  • R 4 and R5 are preferably, independently of one another, each optionally substituted by halogen C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylamino, di- (C 1 -C 6 -alkyl) amino, Ci-Cg- Alkylthio, C 2 -Cg alkenylthio, C3-
  • halogen also as a substituent, such as in haloalkyl, represents fluorine, chlorine, bromine and iodine, in particular fluorine and chlorine.
  • W is particularly preferably are hydrogen, C 4 - alkyl, fluorine, chlorine, tri- fluoromethyl or C ⁇ -C 4 alkoxy,
  • X particularly preferably represents fluorine, chlorine, C1-C4 alkyl, C] -C -alkoxy, C 2 haloalkyl, C ⁇ -C 2 -haloalkoxy or cyano,
  • V 1 particularly preferably represents hydrogen, fluorine, chlorine, bromine, C Cg-alkyl, C r C 4 -alkoxy, C r C 4 -alkylthio, C r C 2 -haloalkyl, C r C 2 -haloalkoxy, nitro , Cyano or phenyl,
  • V 2 particularly preferably represents hydrogen, fluorine, chlorine, C j - - alkyl, Cj-C 4 - alkoxy, C ⁇ -C 2 haloalkyl or C ⁇ -C 2 haloalkoxy,
  • Z particularly preferably represents hydrogen, fluorine, chlorine, C -alkyl, Cj-C 2 -
  • Haloalkyl Cj-C 4 alkoxy or C 1 -C 2 haloalkoxy
  • A, B, C and D particularly preferably each independently represent hydrogen, C r C 4 alkyl, fluorine, chlorine, bromine, iodine, C r C 4 alkoxy, C r C 2 -
  • G particularly preferably represents hydrogen (a) or one of the groups
  • E represents a metal ion or an ammonium ion
  • L represents oxygen or sulfur
  • M oxygen or sulfur
  • R particularly preferably represents C 1 -C 5 -alkyl, C -C 5 -g alkenyl, C - which is optionally mono- to pentas substituted by fluorine or chlorine -
  • phenyl which is optionally mono- to disubstituted by fluorine, chlorine, bromine, cyano, nitro, C 4 -C 4 -alkyl, C 4 -C 4 alkoxy, trifluoromethyl or trifluoromethoxy,
  • R 2 particularly preferably represents C 1 -C 3 -alkyl which is optionally mono- to trisubstituted by fluorine, C 2 -C 8 -alkenyl or C 1 -C 4 -alkoxy-C 2 -C 4 ⁇ alkyl,
  • each phenyl or benzyl optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C1-C4-alkyl, C1-C3-alkoxy, trifluoromethyl or trifluoromethoxy,
  • R 3 particularly preferably represents Ci-Cg-alkyl which is optionally substituted three times by fluorine or is optionally substituted once to twice by fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro phenyl,
  • R 5 stands especially for C j -C alkyl. C j -C 4 alkoxy or C 1 -C alkylthio,
  • R 6 particularly preferably represents hydrogen, Ci-Cg-alkyl, C3-Cg-cycloalkyl, C ⁇ -Cg-alkoxy, C3-Cg-alkenyl, C ⁇ -Cg-alkoxy-C ⁇ -Cg-alkyl, for optionally single to triple by fluorine, chlorine, bromine, trifluoromethyl, Cj-C 4 - alkyl or C 4 - alkoxy-substituted phenyl, represents optionally mono- to disubstituted by fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl or methoxy-substituted benzyl, R 7 particularly preferably represents hydrogen, Cj-Cg-alkyl or C ß- Cg-alkenyl,
  • R 6 and R 7 together particularly preferably represent a C 4 -C 5 alkylene radical which may be substituted by methyl or ethyl and in which a methylene group may have been replaced by oxygen or sulfur.
  • halogen also as a substituent such as in haloalkyl, for fluorine, chlorine, bromine and iodine, especially for fluorine and chlorine, especially for fluorine.
  • W very particularly preferably represents hydrogen, chlorine, methyl, ethyl or methoxy
  • Trifluoromethoxy or cyano (highlighted for chlorine, methyl, ethyl, n-propyl or trifluoromethyl),
  • V 2 very particularly preferably represents hydrogen, fluorine, chlorine, methyl, methoxy or trifluoromethyl
  • Z very particularly preferably represents hydrogen, fluorine, chlorine, methyl, ethyl, methoxy or trifluoromethyl (highlighted for hydrogen, fluorine, chlorine or methyl),
  • A, B, C and D very particularly preferably each independently
  • Hydrogen methyl, ethyl, propyl, isopropyl, tert-butyl, fluorine, chlorine, bromine, iodine, methoxy, ethoxy, isopropoxy, tert-butoxy, trifluoromethyl,
  • G particularly preferably represents hydrogen (a) or one of the groups
  • E represents a metal ion or an ammonium ion
  • L represents oxygen or sulfur
  • M oxygen or sulfur
  • R very particularly preferably represents C 1 -C 4 -alkyl, C 1 -C 4 -alkenyl which is optionally mono- to trisubstituted by fluorine or chlorine,
  • phenyl optionally substituted simply by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, isopropyl, tert-butyl, methoxy, trifluoromethyl or trifluoromethoxy,
  • R 2 very particularly preferably represents C 1 -C 14 -alkyl, C 2 -C] 4-alkenyl or C 1 -C 4 -alkoxy-C 2 -C 3 -alkyl, cyclobutyl, cyclopentyl or cyclohexyl which is optionally mono- to trisubstituted by fluorine,
  • phenyl or benzyl optionally substituted in each case by fluorine, chlorine, cyano, nitro, methyl, ethyl, isopropyl, tert-butyl, methoxy, trifluoromethyl or trifluoromethoxy,
  • R 3 very particularly preferably represents methyl, ethyl which is optionally triple-substituted by fluorine or optionally monosubstituted by fluorine, chlorine
  • R 4 very particularly preferably represents -C4 ⁇ alkyl, -C -C4-alkoxy, C1 -C4- alkylamino, di- (C ⁇ -C4-alkyl) amino, C ⁇ -C4-alkylthio or each optionally simply by fluorine, chlorine , Bromine, nitro, cyano, -C 2 -C alkoxy, trifluoromethoxy or C1 -C3 alkyl substituted phenyl, phenoxy or phenylthio,
  • R 7 very particularly preferably represents hydrogen, C j -C 4 - alkyl or C 3 -C 4 - alkenyl,
  • R 6 and R 7 very particularly preferably represent a C5-Cg-alkylene radical in which a methylene group is optionally replaced by oxygen or sulfur.
  • X particularly preferably represents chlorine, methyl, ethyl, n-propyl or trifluoromethyl
  • V 1 particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, tert-butyl, methoxy, trifluoromethyl or trifluoromethoxy,
  • V 2 particularly preferably represents hydrogen, fluorine, chlorine, methyl, methoxy or trifluoromethyl
  • Z particularly preferably represents hydrogen, chlorine or methyl
  • B and C particularly preferably independently of one another each represent hydrogen, methyl, methoxy, fluorine, chlorine, bromine, iodine or trifluoromethyl,
  • D particularly preferably represents hydrogen or methoxy, with the proviso that at least two of the radicals A, B, C or D represent hydrogen,
  • G particularly preferably represents hydrogen (a) or one of the groups
  • M oxygen or sulfur
  • R particularly preferably represents C 1 -C 6 -alkyl, C 2 -C 4 -alkenyl, methoxymethyl, ethoxymethyl, ethylthiomethyl or in each case cyclopropyl, cyclopentyl or cyclohexyl which is simply substituted by fluorine, chlorine, methyl, ethyl or methoxy,
  • phenyl optionally substituted simply by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, isopropyl, tert-butyl, methoxy, trifluoromethyl or trifluoromethoxy,
  • R ⁇ particularly preferably represents Ci-Cg-alkyl, C 2 -C4-alkenyl or methoxyethyl, ethoxyethyl, propoxyethyl, iso-propoxyethyl, cyclopentyl or cyclohexyl,
  • W stands for hydrogen or methyl
  • X stands for chlorine, methyl or trifluoromethyl
  • V 1 stands for hydrogen, methyl, chlorine, fluorine, trifluoromethyl or trifluoromethoxy
  • V 2 stands for hydrogen, chlorine or trifluoromethyl
  • G stands for hydrogen (a) or for one of the groups
  • M stands for oxygen or sulfur
  • R 1 stands for Cj-Cg-alkyl, for chlorine-substituted phenyl or for chlorine-substituted pyridyl,
  • R 2 stands for Cj-Cg-alkyl, phenyl or benzyl.
  • Saturated or unsaturated hydrocarbon radicals such as alkyl or alkenyl can also be used in connection with heteroatoms, e.g. in alkoxy, where possible, be straight-chain or branched.
  • optionally substituted radicals can be mono- or polysubstituted, and in the case of multiple substitutions the substituents can be the same or different.
  • A, B, C, D, W, X, Y, Z and R & have the meanings given above,
  • acylanthranilic acid esters of the formula (II) are obtained, for example, if anthranilic acid derivatives of the formula (XV)
  • W, X, Y and Z have the meanings given above and
  • A, B, C, D, W, X, Y and Z have the meanings given above,
  • A, B, C, D, W, X, Y and Z have the meanings given above,
  • W, X, Y and Z have the meanings given above and
  • the compounds of formula (XVI) are known. They can be prepared using methods known in principle (WO 99/43 649, WO 99/48 869 and WO 99/55 673).
  • halogenating agents for example thionyl chloride, thionyl bromide, oxalyl chloride, phosgene, phosphorus trichloride, phosphorus tribromide or phosphorus pentachloride
  • a diluent for example optionally chlorinated aluminum phatic or aromatic hydrocarbons such as toluene or methylene chloride
  • Y represents optionally substituted phenyl or hetaryl
  • the process (A) is characterized in that compounds of the formula (II) in which A, B, C, D, W, X, Y, Z and R ⁇ have the meanings given above, in the presence of a base of an intramolecular Subject to condensation.
  • All inert organic solvents can be used as diluents in process (A) according to the invention.
  • Hydrocarbons such as toluene and xylene, preferably ethers, such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycol dimethyl ether, and also polar solvents, such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methylpyrrolidone, and alcohols, such as methanol, ethanol, are preferably usable.
  • All conventional proton acceptors can be used as the base (deprotonating agent) when carrying out process (A) according to the invention.
  • reaction temperatures can be varied within a substantial range. In general, temperatures between -78 ° C and 250 ° C, preferably between -20 ° C and 150 ° C. Process (A) according to the invention is generally carried out under normal pressure.
  • reaction components of the formula (II) and the deprotonating bases are generally employed in approximately double equimolar amounts. However, it is also possible to use one or the other component in a larger excess (up to 3 moles).
  • All solvents which are inert towards the acid halides can be used as diluents in the process (B- ⁇ ) according to the invention.
  • Hydrocarbons such as gasoline, benzene, toluene, xylene and tetralin, preferably halogen hydrocarbons, such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, ketones, such as acetone and methylisopropyl ketone, furthermore ethers, such as diethyl ether, tetrahydrofuran and Dioxane, in addition carboxylic acid esters such as ethyl acetate, nitriles such as acetonitrile and also strongly polar solvents such as dimethylformamide, dimethyl sulfoxide and sulfolane. If the hydrolysis stability of the acid halide permits, the reaction can also be carried out in the presence of water.
  • Process (B- ⁇ ) all usual acid acceptors into consideration.
  • Tertiary amines such as triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecene (DBU), diazabicyclonones (DBN), Hunig base and N, N-dimethylaniline, and also alkaline earth metal oxides, such as magnesium oxide and calcium oxide, are also preferably used Alkali and alkaline earth metal carbonates, such as sodium carbonate, potassium carbonate and calcium carbonate as well as alkali hydroxides such as sodium hydroxide and potassium hydroxide.
  • reaction temperatures in the inventive process (B- ⁇ ) can be varied within a substantial range. Generally one works at
  • the starting materials of the formula (I-a) and the carboxylic acid halide of the formula (III) are generally in each case used in approximately equivalent amounts. However, it is also possible to use the carboxylic acid halide in a larger excess (up to 5 mol). The processing takes place according to usual methods.
  • Process (B- ⁇ ) is characterized in that compounds of the formula (I-a) are reacted with carboxylic anhydrides of the formula (IV), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • the acid binders which are optionally added in process (B- ⁇ ) are preferably those acid binders which are also preferred when using acid halides.
  • the reaction temperatures can be varied within a substantial range in the process (B- ⁇ ) according to the invention. In general, temperatures between -20 ° C and + 150 ° C, preferably between 0 ° C and 100 ° C.
  • the starting materials of the formula (I-a) and the carboxylic anhydride of the formula (IV) are generally used in approximately equivalent amounts in each case. However, it is also possible to use the carboxylic anhydride in a larger excess (up to 5 mol). The processing takes place according to usual methods.
  • the general procedure is to remove diluent and excess carboxylic anhydride and the carboxylic acid formed by distillation or by washing with an organic solvent or with water.
  • Suitable acid binders for the reaction according to process (C) according to the invention are all customary acid acceptors.
  • Tertiary amines such as triethylamine, pyridine, DABCO, DBU, DBA, Hunig base and N, N-dimethylaniline, furthermore alkaline earth metal oxides, such as magnesium and calcium oxide, and also alkali and alkaline earth metal carbonates, such as sodium carbonate, are preferably usable.
  • Diluents which can be used in process (C) according to the invention are all inert to the chloroformates or chloroformates
  • Hydrocarbons are preferably usable, such as gasoline, benzene, toluene, xylene and tetralin, furthermore halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, also ketones such as acetone and methylisopropyl ketone, furthermore ethers such as diethyl ether, tetrahydrofuran and dioxane, in addition carboxylic acid ester , such as ethyl acetate, nitriles such as acetonitrile and also strongly polar solvents, such as
  • reaction temperatures can be varied within a substantial range when carrying out process (C) according to the invention. If you work in the presence of a diluent and an acid binder, they are
  • Reaction temperatures generally between -20 ° C and + 100 ° C, preferably between 0 ° C and 50 ° C.
  • the starting materials of the formula (I-a) and the corresponding chloroformic acid ester or chloroformic acid thiolester of the formula (V) are generally in each case used in approximately equivalent amounts. However, it is also possible to use one or the other component in a larger excess (up to 2 mol).
  • the processing takes place according to usual methods. The general procedure is to remove the precipitated salts and to concentrate the remaining reaction mixture by stripping off the diluent.
  • Process (D) is characterized in that compounds of the formula (Ia) are in each case reacted with compounds of the formula (VI) in the presence of a diluent and, if appropriate, in the presence of an acid binder.
  • a diluent in the presence of a diluent and, if appropriate, in the presence of an acid binder.
  • about 1 mol of chloromothio formate or chlorodithio formate of formula (VI) is reacted at 0 to 120 ° C., preferably at 20 to 60 ° C., per mole of starting compound of the formula (Ia).
  • Possible diluents added are all inert polar organic solvents, such as nitriles, ethers, esters, amides, sulfones, sulfoxides, but also haloalkanes.
  • Acetonitrile, ethyl acetate, dimethyl sulfoxide, tetrahydrofuran, dimethylformamide or methylene chloride are preferably used.
  • the addition of strong deprotonating agents such as e.g. Sodium hydride or potassium tert-butoxide is the enolate salt of the compound (I-a), the further addition of acid binders can be dispensed with.
  • customary inorganic or organic bases are suitable, for example sodium hydroxide, sodium carbonate, potassium carbonate, pyridine, triethylamine.
  • the reaction can be carried out at atmospheric pressure or under elevated pressure, preferably at atmospheric pressure.
  • the processing takes place according to usual methods.
  • Process (E) is characterized in that compounds of the formula (Ia) are in each case reacted with sulfonyl chlorides of the formula (VII), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • sulfonyl chlorides of the formula (VII) if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • about 1 mol of sulfonic acid chloride of the formula (VII) is reacted per mole of starting compound of the formula (Ia) at -20 to 150 ° C., preferably at 20 to 70 ° C.
  • Possible diluents added are all inert polar organic solvents such as esters, ethers, amides, nitriles, sulfones, sulfoxides or halogenated hydrocarbons such as methylene chloride.
  • Acetonitrile, ethyl acetate, dimethyl sulfoxide, tetrahydrofuran, dimethylformamide, methylene chloride are preferably used.
  • the enolate salt of the compound (I-a) is prepared by adding strong deprotonating agents (such as sodium hydride or potassium tert-butoxide), further addition of acid binders can be avoided.
  • strong deprotonating agents such as sodium hydride or potassium tert-butoxide
  • customary inorganic or organic bases are suitable, for example sodium hydroxide, sodium carbonate, potassium carbonate, pyridine, triethylamine.
  • the reaction can be carried out at atmospheric pressure or under elevated pressure, preferably at atmospheric pressure.
  • the processing takes place according to usual methods.
  • Process (F) according to the invention is characterized in that compounds of the formula (I-a) are each reacted with phosphorus compounds of the formula (VIII), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
  • the production process (F) is carried out to obtain compounds of the formula
  • Possible inerting agents added are all inert, polar organic solvents, such as ethers, amides, nitriles, alcohols, sulfides,
  • Acetonitrile, dimethyl sulfoxide, tetrahydrofuran, dimethylformamide, methylene chloride are preferably used.
  • Possible inorganic binders which may be added are conventional inorganic or organic bases, such as hydroxides, carbonates or amines. Examples include sodium hydroxide, sodium carbonate, potassium carbonate, pyridine, triethylamine.
  • the reaction can be carried out under normal pressure or under elevated pressure, preferably under normal pressure.
  • the processing takes place according to the usual methods of organic chemistry.
  • the end products obtained are preferably purified by crystallization, chromatographic purification or by so-called “distillation", i.e. Removal of the volatile
  • Process (G) is characterized in that compounds of the formula (I-a) are reacted with metal hydroxides or metal alkoxides of the formula (IX) or amines of the formula (X), if appropriate in the presence of a diluent.
  • Diluents which can be used in process (G) according to the invention are preferably ethers such as tetrahydrofuran, dioxane, diethyl ether or alcohols such as methanol, ethanol, isopropanol, but also water.
  • Process (G) according to the invention is generally carried out under normal pressure.
  • the reaction temperatures are generally between -20 ° C and 100 ° C, preferably between 0 ° C and 50 ° C.
  • the process (H) according to the invention is characterized in that compounds of the formula (Ia) in each case with (H- ⁇ ) compounds of the formula (XI), if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst or (H-ß) with compounds of the formula (XII) optionally in
  • Possible diluents added are all inert organic solvents, such as nitriles, esters, ethers, amides, nitriles, sulfones, sulfoxides.
  • catalysts can be added to accelerate the reaction.
  • Organic tin compounds such as e.g. Dibutyltin dilaurate can be used. It is preferably carried out at normal pressure.
  • the enolate salt of the compound (I-a) is prepared by adding strong deprotonating agents (such as sodium hydride or potassium tert-butoxide), the further addition of acid binders can be dispensed with.
  • strong deprotonating agents such as sodium hydride or potassium tert-butoxide
  • customary inorganic or organic bases are suitable, for example sodium hydroxide, sodium carbonate, potassium carbonate, triethylamine or pyridine.
  • Palladium (0) complexes are suitable as catalysts for carrying out process (I) according to the invention.
  • tetrakis (triphenylphosphine) palladium is used.
  • Palladium (II) compounds such as bis (triphenylphosphine) palladium (II) chloride are also suitable.
  • Inorganic or organic bases are suitable as acid acceptors for carrying out process (I) according to the invention.
  • These preferably include alkaline earth metal or alkali metal hydroxides, acetates, carbonates or hydrogen carbonates, such as, for example, sodium, potassium, barium or ammonium hydroxide,
  • Cesium fluoride and tertiary amines such as trimethylamine, triethylamine, tributylamine, N, N-dimethylaniline, N, N-dimethylbenzylamine, pyridine, N-methylpiperidine, N-methylmorpholine, N, N-dimethylamino pyridine, diazabicyclooctane (DABCO), diazabicyclonones (DBN) or diazabicyclonecene (DBU).
  • DABCO diazabicyclooctane
  • DBN diazabicyclonones
  • DBU diazabicyclonecene
  • Suitable diluents for carrying out process (I) according to the invention are water, organic solvents and any mixtures thereof.
  • organic solvents are: aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, methylene chloride, chloroform, carbon tetrachloride, dichloro, trichloroethane or carbon tetrachloride; Ethers, such as diethyl, diisopropyl, methyl tert-butyl, methyl tert-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxy
  • reaction temperature in process (I) according to the invention can be varied within a substantial range. In general, temperatures between 0 ° C and + 180 ° C, preferably between 50 ° C and + 150 ° C.
  • boronic acid of the formula (XIV) and compounds of the formulas (I-a) to (I-g) are used in a molar ratio of 1: 1 to 3: 1, preferably 1: 1 to 2: 1.
  • the catalyst is generally used from 0.0005 to 0.5 mol, preferably 0.001 mol to 0.1 mol, per mol of the compounds (I-a) to (I-g).
  • the base is generally used in excess.
  • the active substances are suitable for controlling animal pests, especially insects, Arachnids and nematodes found in agriculture, in forests, in the protection of stocks and materials, and in the hygiene sector. They can preferably be used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the pests mentioned above include:
  • Thysanura e.g. Lepisma saccharina.
  • Orthoptera e.g. Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp., Schistocerca gregaria.
  • Phthiraptera for example Pediculus humanus corporis, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp ..
  • Thysanoptera for example Hercinothrips femoralis, Thrips tabaci, Thrips palmi, Frankliniella accidentalis.
  • Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis,
  • Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis,
  • Phylloc spp. Mamestra brassicae, Panolis flammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionellaanaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaella
  • Anthonomus spp. Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Agribiole spp., Tenebrio molitor. Conoderas spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica, Lissorhoptrus oryzophilus.
  • Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
  • Drosophila melanogaster Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tabanus spp.
  • Tannia spp. Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa, Hylemyia spp., Liriomyza spp ..
  • the plant-parasitic nematodes include, for example, Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Tripusichpp. Spp., Xiphinema spp. ,
  • the compounds according to the invention can also be used in certain concentrations or application rates as herbicides and microbicides, for example as fungicides, antifungal agents and bactericides. If appropriate, they can also be used as intermediates or precursors for the synthesis of further active compounds.
  • plants and parts of plants can be treated.
  • Plants are understood here to mean all plants and plant populations, such as desired and unwanted wild plants or crop plants (including naturally occurring crop plants).
  • Cultivated plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights.
  • Parts and organs of the plants such as sprout, leaf, flower and root, are to be understood, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and
  • the treatment of the plants and parts of plants with the active compounds according to the invention is carried out directly or by acting on their surroundings, living space or storage space according to the customary treatment methods, e.g. by diving,
  • the active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble solvents.
  • Che powder, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances as well as fine encapsulation in polymeric substances.
  • formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is liquid solvents and / or solid
  • Carriers where appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • water is used as an extender, e.g. also organic
  • Solvents are used as auxiliary solvents.
  • the following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g.
  • Petroleum fractions mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • alcohols such as butanol or glycol and their ethers and esters
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • Ammonium salts and natural rock meals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock meals, such as highly disperse silica, aluminum oxide and
  • Silicates as solid carriers for granules are possible: eg broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems ;
  • Possible emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid Esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates;
  • Possible dispersants are: eg lignin sulfite waste liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order, for example, to spread the spectrum of activity or to prevent the development of resistance.
  • fungicides bactericides
  • acaricides nematicides or insecticides
  • synergistic effects are obtained, i.e. the effectiveness of the mixture is greater than the effectiveness of the individual components.
  • Debacarb dichlorophene, diclobutrazole, diclofluanide, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomorph, diniconazole,
  • Mancopper Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metomeclam, Metsulfovax,
  • Oxadixyl Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,
  • Tebuconazole Tebuconazole, tecloftalam, tecnazene, Tetcyclacis, tetraconazole, thiabendazole, Thicyofen, Thifluzamide, thiophanate-methyl, thiram, Tioxymid, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, Triazbutil, triazoxide, Trichlamid, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole,
  • Methantetrathiol sodium salt Methyl 1 - (2,3-dihydro-2,2-dimethyl-1 H-inden-1-yl) - 1 H-imidazole-5-carboxylate, methyl-N- (2,6-dimethylphenyl) -N- (5-isoxazolylcarbonyl) -DL-alaninate, methyl-N- (chloroacetyl) -N- (2,6-dimethylphenyl) -DL-alaninate, N- (2,3-dichloro-4-hydroxyphenyl) - 1 -methyl- cyclohexanecarboxamide. N- (2,6-dimethylphenyl) -2-methoxy-N- (tettahydro-2-oxo-3-furanyl) acetamide 5
  • Azamethiphos Azinphos A, Azinphos M, Azocyclotin, Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillus thuringiensis, Baculoviruses, Beauveria bassiana, Beauveria tenella, Bendiocarb, Benfuracarb, Bensultap, Benzoximate, Betacyfluthrin, Bifenazate, Bifenthrin, Bioethanomifhrin, Bethanomifhrin, Bethinomethrin
  • Fenamiphos Fenazaquin, Fenbutatin oxide, Fenitrothion, Fenothiocarb, Fenoxacrim, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fenvalerate, Fipronil, Fluazinam, Fluazuron, Flubrocythrinate, Flucycloxuron, Flutinoxuron, Fluutinoxin, Fluutinoxin
  • Halofenozide HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene, Imidacloprid, indoxacarb, isazofos, isofenphos, isoxathion, ivermectin,
  • Mecarbam Metaldehyde, Methamidophos, Metharhizin anisopliae, Metharhizin flavoviride, Methidathion, Methiocarb, Methoprene, Methomyl, Methoxyfenozide, Metolcarb, Metoxadiazone, Mevinphos, Milbemectin, Milbemycin, Monocrotophos,
  • Paecilomyces fumosoroseus Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos A, Pirimiphos M, Profenofos, Promecarb, Propargite, Propoxur, Prothiofos, Prothrohrinos, Pothrohrinos, Pothrohrine, Pothrohrinate , Pyridaben, pyridathione, pyrimidifen, pyriproxyfen,
  • the active compounds according to the invention can furthermore be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists.
  • Synergists are compounds through which the action of the active ingredients is increased without the added synergist itself having to be active.
  • the active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges.
  • the active substance concentration of the use forms can be from 0.0000001 to 95% by weight of active substance, preferably between 0.0001 and 1% by weight.
  • the application takes place in a customary manner adapted to the application forms.
  • Active ingredient characterized by an excellent residual effect on wood and clay as well as a good alkali stability on limed substrates.
  • plants and their parts can be treated according to the invention.
  • transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods are treated.
  • Organisms and their parts treated.
  • the term “parts” or “parts of plants” or “plant parts” was explained above.
  • Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention.
  • Plant varieties are plants with new properties ("traits") that are characterized by both conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, bio and genotypes.
  • the treatment according to the invention can also cause superadditive (“synergistic") effects.
  • superadditive for example, reduced application rates and / or widening of the spectrum of action and / or an increase in the action of the substances and agents which can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to
  • Dryness or against water or soil salt content increased flowering performance, easier harvesting, acceleration of ripening, higher harvest yields, higher quality and / or higher nutritional value of the harvested products, higher storability and / or workability of the harvested products, which go beyond the effects that are actually to be expected ,
  • the preferred transgenic (genetically engineered) plants or plant cultivars to be treated according to the invention include all plants which have received genetic material through the genetic engineering modification, which gives these plants particularly advantageous, valuable properties (“traits”).
  • the traits are particularly emphasized as the increased defense of the plants against insects by toxins which arise in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (for example by the genes Cry ⁇ A (a), CryIA (b), Cry ⁇ A (c), CryllA, CrylllA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants (hereinafter "Bt plants”).
  • the properties (“traits”) also emphasize the increased defense of plants against fungi, bacteria and viruses by systemic acquirers
  • Pneumonyssus spp. Stemostoma spp., Varroa spp ..
  • the active compounds of the formula (I) according to the invention are also suitable for controlling arthropods which are used in agricultural animals, e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as e.g. Dogs, cats, house birds, aquarium fish and so-called experimental animals, such as Infest hamsters, guinea pigs, rats and mice. By fighting these arthropods, deaths and
  • the active compounds according to the invention are used in the veterinary sector in a known manner by enteral administration in the form of, for example, tablets, Capsules, watering, drenching, granules, pastes, boluses, the feed-through method, of suppositories, by parenteral administration, such as by injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, by nasal application, by dermal Application in the form of, for example, diving or bathing (dipping), spraying (spray), pouring on (pour-on and spot-on), des
  • Hymenoptera such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur.
  • Termites like Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes fiavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus.
  • Bristle tails such as Lepisma saccharina.
  • the active substances can be used as such, in the form of concentrates or generally customary formulations such as powders, granules, solutions, suspensions, emulsions or pastes.
  • the formulations mentioned can be prepared in a manner known per se, for example by mixing the active ingredients with at least one solvent or diluent, emulsifier, dispersant and / or binder or fixative, water repellants, optionally siccatives and UV stabilizers and added - if necessary dyes and pigments and other processing aids.
  • the insecticidal compositions or concentrates used to protect wood and wood-based materials contain the active ingredient according to the invention in a concentration of 0.0001 to 95% by weight, in particular 0.001 to 60% by weight.
  • organic-chemical solvent or solvent mixture and / or an oily or oily or low-volatility organic-chemical solvent or solvent mixture and / or a polar organic-chemical solvent or solvent mixture and / or water and optionally an emulsifier and / or wetting agents.
  • the organic chemical solvents used are preferably oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C., preferably above 45 ° C.
  • Corresponding mineral oils or their aromatic fractions or mineral oil-containing solvent mixtures, preferably white spirit, petroleum and / or alkylbenzene, are used as such low-volatility, water-insoluble, oily and oily solvents.
  • part of the organic chemical solvent or solvent mixture or an aliphatic polar organic chemical solvent or solvent mixture is replaced.
  • Aliphatic organochemical solvents containing hydroxyl and / or ester and / or ether groups, such as, for example, glycol ethers, esters or the like, are preferably used.
  • the known organic-chemical binders are the water-thinnable and / or synthetic resins which are soluble or dispersible or emulsifiable in the organic-chemical solvents used and / or binding drying oils, in particular binders consisting of or containing an acrylate resin, a vinyl resin, for example polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene-coumarone resin, silicone resin, drying vegetable and / or drying oils and / or physically drying binders based on a Natural and / or synthetic resin used.
  • binders consisting of or containing an acrylate resin, a vinyl resin, for example polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene-coumarone resin
  • the synthetic resin used as a binder can be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances up to 10% by weight can also be used as binders. In addition, known dyes, pigments, water-repellants, odor correctors and inhibitors or anticorrosive agents and the like can be used.
  • At least one alkyd resin or modified alkyd resin and / or a drying vegetable oil is preferably contained in the agent or in the concentrate as the organic chemical binder.
  • Alkyd resins having an oil content of more than 45% by weight, preferably 50 to, are preferred according to the invention
  • binder mentioned can be replaced by a fixing agent (mixture) or a plasticizer (mixture). These additives are intended to prevent volatilization of the active ingredients and crystallization or precipitation. They preferably replace 0.01 to 30% of the binder (based on 100% of the binder used).
  • the plasticizers come from the chemical classes of phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate, phosphoric acid esters such as tributyl phosphate, adipic acid esters such as di- (2-ethylhexyl) adipate, stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, higher glycerol glycerol or glycerol ether - Kolether, glycerol ester and p-toluenesulfonic acid ester.
  • phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate
  • phosphoric acid esters such as tributyl phosphate
  • adipic acid esters such as di- (2-ethylhexyl) adipate
  • Fixing agents are chemically based on polyvinyl alkyl ethers such as e.g. Polyvinyl methyl ether or ketones such as benzophenone, ethylene benzophenone.
  • Water is also particularly suitable as a solvent or diluent, if appropriate in a mixture with one or more of the above-mentioned organic chemical solvents or diluents, emulsifiers and dispersants.
  • a particularly effective wood protection is achieved by industrial impregnation processes, e.g. vacuum, double vacuum or pressure processes.
  • the ready-to-use compositions can optionally contain further insecticides and, if appropriate, one or more fungicides.
  • insecticides and fungicides mentioned in WO 94/29 268 are preferably suitable as additional admixing partners.
  • the compounds mentioned in this document are an integral part of the present application.
  • Insecticides such as chloropyriphos, phoxime, silafluofin, alphamethrin, cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron, transfluthron, trifluoropuron, methifluoropuron, methifluoropuron, methifluoropuron
  • fungicides such as epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, imazalil, dichlorofluoride, tolylfluanid, 3-iodo-2-propynylbutylcarbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro - octylisothiazolin-3-one.
  • the compounds according to the invention can be used to protect objects, in particular ship hulls, sieves, nets, structures, quay systems and signaling systems which come into contact with sea or brackish water.
  • heavy metals such as e.g. in bis (trialkyltin) sulfides, tri-n-butyltin laurate, tri - «- butyltin chloride, copper (I) oxide, triethyltin chloride, tri - « - butyl (2-phenyl-4-chlorophenoxy) tin, tributyltin oxide, molybdenum disulfide , Antimony oxide, polymeric butyl titanate, phenyl- (bispyridine) - bismuth chloride, tri-w-butyltin fluoride, manganese ethylene bisthiocarbamate, zinc dimethyldithiocarbamate, zinc ethylene bisthiocarbamate, zinc and copper salts of 2-pyridinethiol-1-oxide, bisdimethyldihamidoxydiaminodiimidoxydiamidoxydiamidoxydiamidoxy
  • the ready-to-use antifouling paints may also contain other active ingredients, preferably algicides, fungicides, herbicides, molluscicides or other antifouling active ingredients.
  • Suitable combination partners for the antifouling agents according to the invention are preferably:
  • Algicides like 2-tert-butylamino-4-cyclopropylamino-6-methylthio-l, 3,5-triazine, dichlorophene, diuron, endothal, fentin acetate, isoproturon, methabenzthiazuron, oxyfluorfen, quinoclamine and terbutryn;
  • Fentin acetate, metaldehyde, methiocarb, niclosamide, thiodicarb and trimethacarb; or conventional antifouling agents such as
  • the antifouling agents used contain the active compound according to the invention of the compounds according to the invention in a concentration of 0.001 to 50% by weight, in particular of 0.01 to 20% by weight.
  • antifouling agents according to the invention furthermore contain the usual constituents as described, for example, in Ungerer, Chem. Ind. 1985, 37, 730-732 and Williams, Antifouling Marine Coatings, Noyes, Park Ridge, 1973.
  • antifouling paints contain in particular binders.
  • Examples of recognized binders are polyvinyl chloride in a solvent system, chlorinated rubber in a solvent system, acrylic resins in one
  • Solvent system in particular in an aqueous system, vinyl chloride / vinyl acetate copolymer systems in the form of aqueous dispersions or in the form of organic solvent systems, butadiene / styrene / acrylonitrile rubbers, drying oils, such as linseed oil, resin esters or modified hard resins in combination with tar or bitumen, Asphalt as well as epoxy compounds, small amounts of chlorinated rubber, chlorinated polypropylene and vinyl resins.
  • Paints may also contain inorganic pigments, organic pigments or dyes, which are preferably insoluble in sea water. Furthermore, paints can contain materials such as rosin in order to be controlled
  • the paints may also contain plasticizers, modifiers that affect the rheological properties, and other conventional ingredients.
  • the compounds according to the invention or the abovementioned mixtures can also be incorporated into self-polishing antifouling systems.
  • the active ingredients are also suitable for controlling animal pests, in particular insects, arachnids and mites, which live in closed spaces such as apartments, factory halls, offices, vehicle cabins, etc. occurrence.
  • animal pests in particular insects, arachnids and mites, which live in closed spaces such as apartments, factory halls, offices, vehicle cabins, etc. occurrence.
  • insects in particular insects, arachnids and mites
  • they can be used alone or in combination with other active ingredients and auxiliaries in household insecticide products. They are effective against sensitive and resistant species and against all stages of development.
  • insects in particular insects, arachnids and mites, which live in closed spaces such as apartments, factory halls, offices, vehicle cabins, etc. occurrence.
  • auxiliaries in household insecticide products. They are effective against sensitive and resistant species and against all stages of development.
  • Sco ⁇ ionidea for example Buthus occitanus.
  • Acarina for example, Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus for Dermatophagoides for Dermatophisides.
  • Opiliones e.g. Pseudosco ⁇ iones chelifer, Pseudosco ⁇ iones cheiridium, Opiliones phalangium.
  • Diplopoda e.g. Blaniulus guttulatus, Polydesmus spp ..
  • Psocoptera for example Lepinatus spp., Liposcelis spp.
  • Coleptera for example Anthrenus spp., Attagenus spp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp., Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae, Sitophilus zeamais, Stegobium paniceum.
  • Aedes aegypti Aedes albopictus, Aedes taeniorhynchus, Anopheles spp., Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Drosophila domppis, Musanncaestpp., Musanncaotpp , Simulium spp., Stomoxys calcitrans, Tipula paludosa.
  • Lepidoptera e.g. Achroia grisella, Galleria mellonella, Plodia inte ⁇ unctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.
  • Ctenocephalides canis Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.
  • Hymenoptera e.g. Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.
  • the application in the field of household insecticides is carried out alone or in combination with other suitable active compounds such as phosphoric acid esters, carbamates, pyrethroids, growth regulators or active compounds from other known classes of insecticides. They are used in aerosols, sprayless spray agents, e.g. pump and atomizer sprays, automatic fog machines, foggels, foams, gels, vaporization products with vaporization plates made of cellulose or plastic, liquid vaporizers, gel and membrane vaporizers, propeller-driven vaporizers, energy-free or passive vaporization systems, Moth papers, moth bags and
  • suitable active compounds such as phosphoric acid esters, carbamates, pyrethroids, growth regulators or active compounds from other known classes of insecticides. They are used in aerosols, sprayless spray agents, e.g. pump and atomizer sprays, automatic fog machines, foggels, foams, gels, vaporization products with vaporization plates made of cellulose or plastic, liquid vaporizer
  • Moth angels as granules or dusts, in litter edema or bait stations.
  • the active compounds according to the invention can also be used as defoliants, desiccants, haulm killers and in particular as weed killers. Weeds in the broadest sense are all plants that grow in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
  • the active compounds according to the invention can e.g. can be used in the following plants:
  • Lepidium Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenus Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.
  • Apera Avena, Brachiaria, Bromus, Cenchras, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Sagaria, Setaria, Rottboell.
  • the active compounds according to the invention are suitable for combating total weeds, e.g. on industrial and track systems and on paths and squares with and without tree cover.
  • the active compounds according to the invention for weed control in permanent crops e.g. Forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture land and for selective purposes Weed control can be used in annual crops.
  • the compounds of formula (I) according to the invention show strong herbicidal activity and a broad spectrum of activity when used on the soil and on above-ground parts of plants. To a certain extent, they are also suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops, both in the pre-emergence and in the post-emergence process.
  • the active compounds according to the invention can be used in certain concentrations or
  • Application rates can also be used to control animal pests and fungal or bacterial plant diseases. They can be if used as intermediate or Vo ⁇ rodukte for the synthesis of other active ingredients.
  • the active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances.
  • formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, ie liquid solvents and / or solid carriers, optionally using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents.
  • organic solvents can also be used as auxiliary solvents.
  • auxiliary solvents e.g. organic solvents
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, e.g.
  • Petroleum fractions mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • alcohols such as butanol or glycol and their ethers and esters
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • Possible solid carriers are: e.g. Ammonium salts and natural rock powders, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates, are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite,
  • Possible emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersing agents are, for example, lignin sulfite waste liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids, can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight
  • Active ingredient preferably between 0.5 and 90%.
  • the active compounds according to the invention can also be used in a mixture with known herbicides and / or with substances which improve crop tolerance (“safeners”) for weed control, finished formulations or tank mixes being possible. Mixtures are therefore also possible possible with weed control agents which contain one or more known herbicides and a safener.
  • safeners substances which improve crop tolerance
  • herbicides are suitable for the mixtures, for example Acetochlor, Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ametryne, Amicarbazone, Amidochlor, Amidosulfuron, Anilofos, Asulam, Atrazme, Azafenidin, Azimsulfuron, Beflubutamid, Benazolin (-ethyl), Benfureson -methyl), bentazone, benzfendizone, benzobicyclone, benzofenap, benzoylprop (-ethyl), bialaphos, bifenox, bispyribac (-sodium), bromobutide, bromofenoxime,
  • the active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the usual way, e.g. by pouring, spraying,
  • the active compounds according to the invention can be applied both before and after emergence of the plants. They can also be worked into the soil before sowing.
  • the amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general, the application rates are between 1 g and 10 kg of active ingredient per hectare of soil, preferably between 5 g and 5 kg per ha.
  • Fungicides can be used in crop protection to combat Plasmodiophoromyces, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
  • Erwinia species such as, for example, Erwinia amylovora
  • Pythium species such as, for example, Pythium ultimum
  • Phytophthora species such as, for example, Phytophthora infestans
  • Bremia species such as, for example, Bremia lactucae
  • Peronospora species such as, for example, Peronospora pisi or P. brassicae;
  • Erysiphe species such as, for example, Erysiphe graminis
  • Sphaerotheca species such as, for example, Sphaerotheca fuliginea
  • Podosphaera species such as, for example, Podosphaera leucotricha
  • Venturia species such as, for example, Venturia inaequalis
  • Pyrenophora species such as, for example, Pyrenophora teres or P. graminea
  • Drechslera (Conidial form: Drechslera, Syn: Helminthosporium);
  • Cochliobolus species such as, for example, Cochliobolus sativus
  • Drechslera (Conidial form: Drechslera, Syn: Helminthosporium);
  • Uromyces species such as, for example, Uromyces appendicularus
  • Puccinia species such as, for example, Puccinia recondita
  • Sclerotinia species such as, for example, Sclerotinia sclerotiorum
  • Tilletia species such as, for example, Tilletia caries
  • Ustilago species such as, for example, Ustilago nuda or Ustilago avenae;
  • Pellicularia species such as, for example, Pellicularia sasakii;
  • Pyricularia species such as, for example, Pyricularia oryzae
  • Fusarium species such as, for example, Fusarium culmorum
  • Septoria species such as, for example, Septoria nodorum
  • Cercospora species such as, for example, Cercospora canescens
  • the active compounds according to the invention also have a strong strengthening effect in plants. They are therefore suitable for mobilizing the plant's own defenses against attack by unwanted microorganisms.
  • Plant-strengthening (resistance-inducing) substances are to be understood in the present context as those substances which are able to stimulate the defense system of plants in such a way that the treated plants develop extensive resistance to these microorganisms when subsequently inoculated with undesirable microorganisms.
  • Undesired microorganisms are to be understood in the present case as phytopathogenic fungi, bacteria and viruses.
  • the substances according to the invention can therefore be used to protect plants against attack by the named pathogens within a certain period of time after the treatment.
  • the active compounds according to the invention are also suitable for increasing the crop yield. They are also less toxic and have good plant tolerance.
  • the active compounds according to the invention can also be used in certain concentrations and application rates as herbicides, for influencing plant growth, and for controlling animal pests. If appropriate, they can also be used as intermediates and products for the synthesis of further active ingredients.
  • Altemaria such as Altemaria tenuis
  • Altemaria tenuis such as Altemaria tenuis
  • Lentinus such as Lentinus tigrinus
  • Penicillium such as Penicillium glaucum
  • Polyporus such as Polyporus versicolor
  • Sclerophoma such as Sclerophoma pityophila
  • Escherichia such as Escherichia coli
  • Pseudomonas such as Pseudomonas aeruginosa
  • Staphylococcus such as Staphylococcus aureus.
  • formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • water e.g. organic solvents can also be used as auxiliary solvents.
  • aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic
  • Hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic table hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, alcohols, such as butanol or glycol, and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
  • Liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide.
  • solid carriers for example, natural rock powders, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates.
  • Possible solid carriers for granules are: eg broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules made from inorganic and organic flours as well as granules made from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks.
  • emulsifiers and / or foaming agents come in
  • nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates.
  • Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • the active compounds according to the invention can also be used in a mixture with known fungicides, bactericides, acaricides, nematicides or insecticides, in order, for example, to spread the spectrum of activity or to prevent the development of resistance.
  • fungicides bactericides
  • acaricides nematicides or insecticides
  • synergistic effects are obtained, i.e. the effectiveness of the mixture is greater than the effectiveness of the individual components.
  • Debacarb dichlorophene, diclobutrazole, diclofluanid, diclomezin, dicloran, diethofencarb, difenoconazole, dimethirimol, dimethomo ⁇ h, diniconazole, diniconazol-M, dinocap, diphenylamine, dipyrithione, ditalimfos, dithianonodol, dithianonodol, dithianonodol, dithianon, dithianon, dithianon, dithianon, dithianon, dithianon, dithianon, dithianon, dithianon, dithianon, dithianon, dithianon, dithianon, dithianon, dithianon, dithianon, dithianon, dithianon, dithianon, dithianon, dithianon, dithianon, dithianon, dithianon, dithianon, dit
  • Imazalil Imibenconazol, Iminoctadin, Iminoctadmealbesilat, Iminoctadinetriacetat, Iodocarb, Ipconazol, Iprobefos (IBP), Iprodione, Irumamycin, Isoprothiolan, Isovaledione,
  • Mancopper Mancozeb, Maneb, Meferimzone, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, Methfuroxam, Metiram, Metomeclam, Metsulfovax, Mildiomycin, Myclobutanil, Myclozolin,
  • Oxadixyl Oxamocarb, Oxolinicacid, Oxycarboxim, Oxyfenthiin,
  • Tridemo ⁇ h Trifloxystrobin, triflumizole, triforin, triticonazole,
  • Fenamiphos fenazaquin, fenbutatin oxide, fenitrothion, fenothiocarb, fenoxacrim
  • Fenoxycarb fenpropathrin, fenpyrad, fenpyrithrin, fenpyroximate, fenvalerate, fipronil, fluazinam, fluazuron, flubrocythrinate, flucycloxuron, flucythrinate, flufenoxuron, flumethrin, flutenzine, fluvalinate, fonophan, furosfiazarbof, fosarbiazil
  • Halofenozide HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene,
  • Triarathenes triazamates, triazophos, triazuron, trichlophenidines, trichlorfon, triflumuron, trimethacarb,
  • the compounds of formula (I) according to the invention also have very good antifungal effects. They have a very broad antimycotic spectrum of activity, in particular against dermatophytes and sprout fungi, mold and diphasic fungi (for example against Candida species such as Candida albicans, Candida glabrata) as well as Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and Aspergillusophieston fumigatus fumigatus like Trichophyton mentagrophytes,
  • Microsporon species such as Microsporon canis and audouinii.
  • the list of these fungi in no way represents a limitation of the detectable mycotic spectrum, but is only of an explanatory nature.
  • the active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules. They are used in the usual way, e.g. by pouring, spraying, spraying, scattering, dusting, foaming, brushing, etc. It is also possible to use the
  • the application rates can be varied within a relatively wide range, depending on the type of application.
  • the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 10 and 1,000 g / ha. In the case of seed treatment, the active compound application rates are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed. In the treatment of the soil, the active compound application rates are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.
  • the mixture is stirred under reflux for 1 day.
  • the solvent is distilled off and the residue is dissolved in dichloromethane and washed with 0.5 N sodium hydroxide solution.
  • Solvent 7 parts by weight of dimethylformamide emulsifier: 2 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Vessels are filled with sand, active ingredient solution, Meloidogyne incognita egg larva suspension and lettuce seeds.
  • the lettuce seeds germinate and the plantlets develop.
  • the galls develop at the roots.
  • the nematicidal effect is determined in% using the formation of bile. 100% means that no galls were found; 0% means that the number of galls on the treated plants corresponds to that of the untreated control.
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with larvae of the horseradish leaf beetle (Phaedon cochleariae) while the leaves are still moist.
  • Solvent 7 parts by weight of dimethylformamide emulsifier: 2 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted to the desired concentration with water containing emulsifier.
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with caterpillars of the cockroach (Plutella xylostella) while the leaves are still moist.
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted to the desired concentration with water containing emulsifier.
  • Cabbage leaves (Brassica oleracea) are treated by dipping into the preparation of active ingredient of the desired concentration and with caterpillars of the army worm
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted to the desired concentration with water containing emulsifier.
  • Cabbage leaves (Brassica oleracea) are treated by dipping into the preparation of active ingredient of the desired concentration and with caterpillars of the army worm
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
  • Emulsifier 2 parts by weight of alkylaryl polyglycol ether
  • Bean plants Phaseolus vulgaris
  • Tetranychus urticae which are heavily infested with all stages of the common spider mite (Tetranychus urticae), are immersed in an active ingredient preparation of the desired concentration.
  • the effect is determined in%. 100% means that all spider mites have been killed; 0% means that no spider mites have been killed.
  • Emulsifier 1 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.
  • Evaluation is carried out 7 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • dimethylacetamide emulsifier 1.0 part by weight of alkyl aryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • Evaluation is carried out 10 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • dimethylacetamide emulsifier 1.0 part by weight of alkyl aryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • Sphaerotheca fuliginea inoculated The plants are then placed in the greenhouse at about 23 ° C. and a relative atmospheric humidity of about 70%.
  • Evaluation is carried out 7 days after the inoculation. 0% means an efficiency that corresponds to that of the control, while an efficiency of 100% means that no infection is observed.
  • dimethylacetamide emulsifier 1.0 part by weight of alkyl aryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the concentrate is diluted with water to the desired concentration.
  • the plants are then placed in a greenhouse at approx. 21 ° C and a relative humidity of approx. 90%.
  • Botrytis test (bean) / protective
  • dimethylacetamide emulsifier 1.0 part by weight of alkyl aryl polyglycol ether

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
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  • Engineering & Computer Science (AREA)
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  • General Health & Medical Sciences (AREA)
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Abstract

La présente invention se rapporte à de nouvelles 4-hydroxy-quinolones, substituées par biphényle, de formule (I), dans laquelle A, B, C, D, G, W, X, Y et Z ont les significations indiquées dans la description, à plusieurs procédés de production desdites quinolones et à leur utilisation comme pesticides, microbicides et herbicides.
PCT/EP2002/007570 2001-07-20 2002-07-08 4-hydroxy-quinolones substituees par biphenyle et leur utilisation comme pesticides et herbicides WO2003010145A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
BR0211343-0A BR0211343A (pt) 2001-07-20 2002-07-08 4-hidróxi-quinolonas substituìdas por biefenila e aplicação das mesmas como composições praguicidas e herbicidas
MXPA04000579A MXPA04000579A (es) 2001-07-20 2002-07-08 4-hidroxi-quinolonas bifenilsubstituidas y su uso como agentes pesticidas y herbicidas.
EP02754845A EP1412333A1 (fr) 2001-07-20 2002-07-08 4-hydroxy-quinolones substituees par biphenyle et leur utilisation comme pesticides et herbicides
KR10-2003-7017189A KR20040031710A (ko) 2001-07-20 2002-07-08 비페닐-치환된 4-하이드록시-퀴놀론 및 살해충제 및제초제로서의 그의 용도
JP2003515504A JP2005500339A (ja) 2001-07-20 2002-07-08 ビフェニル置換４−ヒドロキシ−キノロン類ならびに農薬および除草剤としてのそれの使用

Applications Claiming Priority (2)

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DE10135466A DE10135466A1 (de) 2001-07-20 2001-07-20 Biphenylsubstituierte 4-Hydroxy-chinolone
DE10135466.5 2001-07-20

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WO2003010145A1 true WO2003010145A1 (fr) 2003-02-06

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EP (1) EP1412333A1 (fr)
JP (1) JP2005500339A (fr)
KR (1) KR20040031710A (fr)
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DE (1) DE10135466A1 (fr)
MX (1) MXPA04000579A (fr)
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WO2008009908A1 (fr) * 2006-07-20 2008-01-24 Syngenta Limited Dérivés de pyrido [2, 3-b] pyrazine utilisés comme composés herbicides
EP1981341A2 (fr) * 2006-01-30 2008-10-22 Merck and Co., Inc. Inhibiteurs de la synthase d'acides gras (fas)
US7446222B2 (en) 2002-11-01 2008-11-04 Glaxo Group Limited Phenyl compounds
WO2009090401A2 (fr) * 2008-01-17 2009-07-23 Syngenta Limited Composés herbicides
WO2009090402A2 (fr) * 2008-01-17 2009-07-23 Syngenta Limited Composés herbicides
WO2011058036A1 (fr) * 2009-11-13 2011-05-19 Basf Se Composés tricycliques ayant un effet herbicide
CN103508950A (zh) * 2012-06-25 2014-01-15 南开大学 含亚胺结构的4-羟基-2-喹啉酮类化合物及其制备和应用
US9000189B2 (en) 2006-12-04 2015-04-07 Bayer Cropscience Ag Biphenyl-substituted spirocyclic ketoenols
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EP1981341A4 (fr) * 2006-01-30 2011-01-05 Merck Sharp & Dohme Inhibiteurs de la synthase d'acides gras (fas)
EP1981341A2 (fr) * 2006-01-30 2008-10-22 Merck and Co., Inc. Inhibiteurs de la synthase d'acides gras (fas)
US8133847B2 (en) 2006-07-20 2012-03-13 Syngenta Limited Pyrido[2,3-B]pyrazine derivatives useful as herbicidal compounds
WO2008009908A1 (fr) * 2006-07-20 2008-01-24 Syngenta Limited Dérivés de pyrido [2, 3-b] pyrazine utilisés comme composés herbicides
EA016143B1 (ru) * 2006-07-20 2012-02-28 Зингента Лимитед ПРОИЗВОДНЫЕ ПИРИДО[2,3-b]ПИРАЗИНА, ПРИМЕНИМЫЕ В КАЧЕСТВЕ ГЕРБИЦИДНЫХ СОЕДИНЕНИЙ
US9000189B2 (en) 2006-12-04 2015-04-07 Bayer Cropscience Ag Biphenyl-substituted spirocyclic ketoenols
WO2009090402A3 (fr) * 2008-01-17 2010-06-24 Syngenta Limited Composés herbicides
US8557840B2 (en) 2008-01-17 2013-10-15 Syngenta Limited Herbicidal compounds
WO2009090401A3 (fr) * 2008-01-17 2010-09-10 Syngenta Limited Composés herbicides
WO2009090402A2 (fr) * 2008-01-17 2009-07-23 Syngenta Limited Composés herbicides
US8338598B2 (en) 2008-01-17 2012-12-25 Syngenta Limited Herbicidal pyrido[2,3-B]pyrazines and their use as herbicides
EA017629B1 (ru) * 2008-01-17 2013-01-30 Синджента Лимитед Гербицидные соединения
AU2009204688B2 (en) * 2008-01-17 2013-09-26 Syngenta Limited Herbicidal compounds
WO2009090401A2 (fr) * 2008-01-17 2009-07-23 Syngenta Limited Composés herbicides
EA018801B1 (ru) * 2008-01-17 2013-10-30 Синджента Лимитед Гербицидные соединения
US8987455B2 (en) 2008-01-17 2015-03-24 Syngenta Limited Herbicidal compounds
US8653078B2 (en) 2008-01-17 2014-02-18 Syngenta Limited Herbicidal pyrido[2,3-b]pyrazines
WO2011058036A1 (fr) * 2009-11-13 2011-05-19 Basf Se Composés tricycliques ayant un effet herbicide
CN103508950A (zh) * 2012-06-25 2014-01-15 南开大学 含亚胺结构的4-羟基-2-喹啉酮类化合物及其制备和应用
CN103508950B (zh) * 2012-06-25 2016-04-20 南开大学 含亚胺结构的4-羟基-2-喹啉酮类化合物及其制备和应用
CN113880840A (zh) * 2020-07-01 2022-01-04 海利尔药业集团股份有限公司 一种喹啉酚类衍生物或其作为农药可接受的盐、组合物及其用途
WO2022001047A1 (fr) * 2020-07-01 2022-01-06 海利尔药业集团股份有限公司 Dérivé de quinoléine phénol ou sel à activité pesticide acceptable de celui-ci, composition et utilisation associée

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EP1412333A1 (fr) 2004-04-28
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MXPA04000579A (es) 2004-04-20
KR20040031710A (ko) 2004-04-13
JP2005500339A (ja) 2005-01-06

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