EP1001938A1 - 2-benzoyl-cylcohexane-1,3-dione a usage d'herbicide - Google Patents

2-benzoyl-cylcohexane-1,3-dione a usage d'herbicide

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Publication number
EP1001938A1
EP1001938A1 EP98942611A EP98942611A EP1001938A1 EP 1001938 A1 EP1001938 A1 EP 1001938A1 EP 98942611 A EP98942611 A EP 98942611A EP 98942611 A EP98942611 A EP 98942611A EP 1001938 A1 EP1001938 A1 EP 1001938A1
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EP
European Patent Office
Prior art keywords
alkyl
formula
cyclohexane
methyl
hydrogen
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.)
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Application number
EP98942611A
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German (de)
English (en)
Inventor
Stefan Engel
Joachim Rheinheimer
Ernst Baumann
Wolfgang Von Deyn
Regina Luise Hill
Guido Mayer
Ulf Misslitz
Oliver Wagner
Matthias Witschel
Martina Otten
Helmut Walter
Karl-Otto Westphalen
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BASF SE
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BASF SE
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Application filed by BASF SE filed Critical BASF SE
Priority to EP10184196A priority Critical patent/EP2343276A1/fr
Publication of EP1001938A1 publication Critical patent/EP1001938A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/20—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
    • C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
    • C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
    • C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D305/04—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D305/06—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D307/28—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms

Definitions

  • the present invention relates to substituted 2-benzoyl-cyclohexane-1,3-diones of the formula I.
  • R 1 , R 2 are hydrogen, mercapto, nitro, halogen, cyano, rhodano, Ci-Cg-alkyl, Ci-C ⁇ -haloalkyl, Ci-Cg-alkoxy,
  • R 3 are hydrogen, C 5 -alkyl, C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 5 alkynyl, P enyl or Phe nyl-Ci-C ⁇ alkyl; wherein the alkyl radicals mentioned can be partially or completely halogenated and / or can carry one to three of the following groups:
  • n 0, 1 or 2;
  • Q is an optionally substituted cyclohexane-1, 3-dione ring linked in the 2-position;
  • X 1 is a straight-chain or branched Ci-Cg-alkylene, one
  • Oxygen or sulfur is interrupted and the alkyl, alkenyl or alkynyl radicals mentioned can be partially halogenated and / or can carry one to three of the following groups:
  • R 4 is hydrogen, -CC 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, phenyl, phenyl-C 1 -C 6 -alkyl, the alkyl, alkenyl or alkynyl radicals mentioned being partially or completely halogenated can be and / or can be substituted by one or more of the following radicals:
  • heterocyclic or heteroaromatic group may be partially or completely halogenated and / or may be substituted by R 5 ;
  • R 5 is hydrogen, hydroxy, mercapto, amino, cyano, nitro, formyl, C ⁇ -C 4 -alkylamino, C ⁇ -C 4 -dialkylamino, C ⁇ -C 4 -alkoxycarbonyl, C ⁇ -C 4 -alkylcarbonyl, C ⁇ -C 4 -alkyl - carbonyloxy, C 1 -C 4 -alkyl, C 4 haloalkyl, C ⁇ -C -alkylthio, C ⁇ -C4-haloalkylthio, C ⁇ -C 4 -alkoxy, halo-C 4 alkoxy, wherein in all cases the alkyl radicals are each substituted by one or more of the following radicals could be:
  • the invention relates to processes and intermediates for the preparation of compounds of the formula I, compositions which contain them, and the use of the compounds of the formula I and compositions containing them for controlling harmful plants.
  • 2-Benzoylcyclohexan-1,3-diones are known from the literature, for example from EP-A 278 742, EP-A 298 680, EP-A 320 864 and WO 96/14285.
  • herbicidal compositions which contain the compounds I and have a very good herbicidal action.
  • processes for the preparation of these compositions and processes for controlling unwanted vegetation using the compounds I have been found.
  • the present invention also relates to stereoisomers of the compounds of the formula I. Both pure stereoisomers and mixtures thereof are covered.
  • the compounds of the formula I can contain one or more centers of chirality and are then in the form of
  • Enantiomers or mixtures of diastereomers relate both to the pure enantiomers or diastereomers and to their mixtures.
  • the compounds of the formula I can also be present in the form of their agriculturally useful salts, the type of salt generally not being important. In general, the salts of those cations or the acid addition salts of those acids, the cations or anions of which do not adversely affect the herbicidal activity of the compounds I come into consideration.
  • alkali metals preferably lithium, sodium and potassium
  • the alkaline earth metals preferably calcium and magnesium
  • the transition metals preferably manganese, copper, zinc and iron, and ammonium
  • one to four hydrogen atoms by C ⁇ -C-alkyl or hydroxy -CC-C-alkyl and / or a phenyl or benzyl can be replaced, preferably diisopropylammonium
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of C ⁇ -C 4 -alkanoic acids, preferably formate, acylate , Propionate and butyrate.
  • variable Q representing a cyclohexane-1,3-dione ring of the formula II linked in the 2-position
  • R 6 , R 7 , R 9 and R u represent hydrogen or C- L -C 4 alkyl
  • R8 represents hydrogen, -CC 4 -alkyl or C 3 -C -cycloalkyI, where the latter two groups can carry one to three of the following substituents: halogen, -C-C 4 -alkylthio or -C-C 4 -alkoxy;
  • Rio f ur are hydrogen, C 4 alkyl or Cj-Ce-alkoxycarbonyl
  • R 8 and R 11 together form a ⁇ bond or a three- to six-membered carbocyclic ring
  • iji stands for a nucleophilically exchangeable leaving group, such as halogen z. B. bromine, chlorine, hetaryl, e.g. B. imidazolyl, pyridyl, carboxylate, e.g. B. acetate, trifluoroacetate etc.
  • the activated carboxylic acid can be used directly, as in the case of the carboxylic acid halides or generated in situ, e.g. B. with dicyclohexylcarbodiimide, triphenylphosphine / azodicarboxylic acid ester, 2-pyridine disulfide / triphenylphosphine, carbonyldiimidazole Etc.
  • auxiliary base it may be advantageous to carry out the acylation reaction in the presence of a base.
  • the reactants and the auxiliary base are expediently used in equimolar amounts.
  • a small excess of the auxiliary base z. B. 1.2 to 1.5 molar equivalents, based on II, may be advantageous under certain circumstances.
  • Tertiary alkyl amines, pyridine or alkali metal carbonates are suitable as auxiliary bases.
  • a solvent for. B. chlorinated hydrocarbons such as methylene chloride, 1, 2-dichloroethane, aromatic hydrocarbons such as toluene, xylene, chlorobenzene, ethers such as diethyl ether, methyl tert. butyl ether, tetrahydrofuran, dioxane, polar aprotic solvents such as acetonitrile, dimethylformamide, dimethyl sulfoxide or esters such as ethyl acetate or mixtures thereof can be used.
  • chlorinated hydrocarbons such as methylene chloride, 1, 2-dichloroethane, aromatic hydrocarbons such as toluene, xylene, chlorobenzene, ethers such as diethyl ether, methyl tert. butyl ether, tetrahydrofuran
  • carboxylic acid halides are used as the activated carboxylic acid component, it may be expedient to cool the reaction mixture to 0-10 ° C. when this reactant is added. The mixture is then stirred at 20-100 ° C., preferably at 25-50 ° C., until the reaction is complete. The workup is carried out in the usual manner, for. B. the reaction mixture is poured onto water, the product of value extracted. Methylene chloride, diethyl ether and ethyl acetate are particularly suitable as solvents for this. After drying the organic phase and removing the solvent, the crude enol ester of formula IV is preferably purified by chromatography. However, it is also possible to use the crude enol ester of the formula IV for rearrangement without further purification.
  • the rearrangement of the enol esters of the formula IV to the compounds of the formula I is advantageously carried out at from 20 to 40 ° C. in a solvent and in the presence of a base and, if appropriate, in the presence of a cyano compound.
  • acetonitrile methylene chloride, 1, 2-dichloroethane, dioxane, ethyl acetate, toluene or mixtures thereof.
  • Preferred solvents are acetonitrile and dioxane.
  • Suitable bases are tertiary amines such as triethylamine, pyridine or alkali carbonates such as sodium carbonate, potassium carbonate, which are preferably used in an equimolar amount or up to a fourfold excess, based on the ester.
  • Inorganic cyanides such as sodium cyanide, potassium cyanide and organic cyano compounds such as acetone cyanohydrin and trimethylsilycyanide are suitable as cyano compounds. They are used in an amount of 1 to 50 mole percent, based on the ester. Acetone cyanohydrin or trimethylsilyl cyanide, e.g. B. in an amount of 5 to 15, preferably 10 mol percent, based on the ester. 0
  • Alkali carbonates such as potassium carbonate, in acetonitrile or dioxane are particularly preferably used.
  • the processing can be carried out in a manner known per se.
  • the reaction mixture is e.g. B. acidified with dilute mineral acid, such as 5% hydrochloric acid or sulfuric acid, with an organic solvent, e.g. B. extracted methylene chloride, ethyl acetate.
  • the organic extract can with 5 - 10% alkali Q carbonate solution, e.g. B. sodium carbonate, potassium carbonate solution.
  • the aqueous phase is acidified and the precipitate formed is suction filtered and / or extracted with methylene chloride or ethyl acetate, dried and concentrated.
  • R 1 , R 2 hydrogen, mercapto, nitro, halogen, cyano, rhodano, Ci-Ce-alkyl, Ci-C ⁇ -haloalkyl, -C-C 6 alkoxy, C 2 -C 6 alkenyl, C 2 -C 6 -Alkynyl, -OR 3 , -OCOR 3 , -0S0 2 R 3 , 0 -S (0) n R 3 , -S0 2 OR 3 , -S0 2 N (R 3 ) 2 , -NR 3 S0 2 R 3 or -NR 3 COR 3 ;
  • R 3 are hydrogen, C 6 -alkyl, C 6 haloalkyl, C 2 -C 5 alkenyl, C 2 -C 6 -alkynyl, phenyl or 5 Phe nyl-Ci-C ⁇ alkyl; wherein said alkyl radicals can be partially or completely halogenated and / or one can carry up to three of the following groups:
  • n 0.1 or 2;
  • X 1 is a straight-chain or branched Ci-C ß -alkylene-, a
  • alkylene, alkenylene or alkynylene radicals mentioned can be partially halogenated and / or can carry one to three of the following groups:
  • R 4 is hydrogen, -CC 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, phenyl, phenyl-C 1 -C 6 -alkyl, the alkyl, alkenyl or alkynyl radicals mentioned being partially or completely halogenated can be and / or can be substituted by one or more of the following radicals:
  • Nitrogen, oxygen or sulfur, wherein said heterocyclic or heteroaromatic group may be partially or completely halogenated and / or may be substituted by R 3 ;
  • R 5 is hydrogen, hydroxy, mercapto, amino, cyano, nitro, formyl, C 1 -C 4 -alkylamino, C 1 -C 4 -dialkylamino, C ⁇ -C 4 -alkoxycarbonyl, C ⁇ -C 4 -alkylcarbonyl, C ⁇ -C 4 -alkyl - carbonyloxy, C ⁇ -C4-alkyl, C ⁇ -C4-haloalkyl, C ⁇ -C4 ⁇ alkyl thio, C ⁇ -C4-haloalkylthio, C ⁇ -C4-alkoxy, C ⁇ -C4-halo-alkoxy, wherein the alkyl radicals can in each case be substituted by one or more of the following radicals:
  • R 12 is hydroxy or a hydrolyzable residue.
  • hydrolyzable radicals are alkoxy, phenoxy, alkylthio, phenylthio radicals which can be substituted, halides, hetaryl radicals which are bonded via nitrogen, amino or imino radicals which can be substituted, etc.
  • L 1 is halogen, in particular chlorine or bromine.
  • halogenating reagents such as thionyl chloride, thionyl bromide, phosgene, diphosgene, triphosgene, oxalyl chloride and oxalyl bromide
  • the benzoic acid esters of the formula IIIc according to the invention can be obtained by various methods known from the literature (e.g. a. G. Dittus in Houben-Weyl, Methods of Organic Chemistry, Volume V / 3, Sauer- 'Stoff -educationen I, 4th Edition, p. 493 ff., Georg Thieme Verlag, 1965; b. TL Gilchrist, Heterocyclenchemie, 2nd ed., Verlag Chemie, 1995), as illustrated in the examples below.
  • L 2 is a suitable, nucleophilically exchangeable leaving group, such as halogen, for example bromine, chlorine, hetaryl, for example imidazolyl, pyridyl, carboxylate, for example acetate, trifluoroacetate, sulfonate, for example mesylate, Triflate etc.
  • halogen for example bromine, chlorine, hetaryl, for example imidazolyl, pyridyl, carboxylate, for example acetate, trifluoroacetate, sulfonate, for example mesylate, Triflate etc.
  • X 2 represents a straight-chain or branched alkylene, an alkenylene or an alkynylene chain with at least one and at most five carbon atoms,
  • alkylene, alkenylene or alkynylene radicals mentioned can be partially halogenated and / or can carry one to three of the following groups:
  • X 3 represents a straight-chain or branched alkylene, an alkenylene or an alkynylene chain with at most five carbon atoms,
  • alkylene, alkenylene or alkynylene radicals mentioned can be partially halogenated and / or can carry one to three of the following groups:
  • X 2 OX 3 form the variable X 1 .
  • the starting compounds are generally used in an equimolar ratio. However, it can also be advantageous to use one or the other component in excess.
  • auxiliary base it may be advantageous to carry out the reaction in the presence of a base.
  • the reactants and the auxiliary base are expediently used in equimolar amounts.
  • An excess of the auxiliary base e.g. 1.5 to 3 molar equivalents, based on Va, can be advantageous under certain circumstances.
  • Suitable auxiliary bases are tertiary alkyl amines such as triethylamine, pyridine, alkali metal carbonates, e.g. Sodium carbonate, potassium carbonate and alkali metal hydrides, e.g. Sodium hydride. Triethylamine, pyridine and potassium carbonate are preferably used.
  • solvents examples include chlorinated hydrocarbons such as methylene chloride, 1, 2-dichloroethane, aromatic hydrocarbons e.g. Toluene, xylene, chlorobenzene, ethers, such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran, dioxane, polar aprotic solvents, such as acetonitrile, dimethylformamide, dimethyl sulfoxide or esters, such as ethyl acetate, or mixtures thereof.
  • chlorinated hydrocarbons such as methylene chloride, 1, 2-dichloroethane
  • aromatic hydrocarbons e.g. Toluene, xylene, chlorobenzene
  • ethers such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran, dioxane
  • polar aprotic solvents such as acetonitrile
  • reaction temperature is in the range from 0 ° C. to the boiling point of the reaction mixture.
  • L 2 is a suitable, nucleophilically exchangeable leaving group, such as halogen, for example bromine, chlorine, hetaryl, for example imidazolyl, pyridyl, carboxylate, e.g. acetate, trifluoroacetate, sulfonate, e.g. mesylate, triflate etc.,
  • halogen for example bromine, chlorine, hetaryl, for example imidazolyl, pyridyl, carboxylate, e.g. acetate, trifluoroacetate, sulfonate, e.g. mesylate, triflate etc.
  • X 2 represents a straight-chain or branched alkylene, an alkenylene or an alkynylene chain with at least one and at most five carbon atoms,
  • alkylene, alkenylene or alkynylene radicals mentioned can be partially halogenated and / or can carry one to three of the following groups:
  • X 3 represents a straight-chain or branched alkylene, an alkenylene or an alkynylene chain with at most five carbon atoms,
  • alkylene, alkenylene or alkynylene radicals mentioned can be partially halogenated and / or can carry one to three of the following groups:
  • the starting compounds are generally used in an equimolar ratio. However, it can also be advantageous to use one or the other component in excess.
  • auxiliary base it may be advantageous to carry out the reaction in the presence of a base.
  • the reactants and the auxiliary base are expediently used in equimolar amounts.
  • An excess of the auxiliary base, for example 1.5 to 3 molar equivalents, based on VII, can be advantageous under certain circumstances.
  • Suitable auxiliary bases are tertiary alkyl amines such as triethylamine, pyridine, alkali metal carbonates, e.g. Sodium carbonate, potassium carbonate and alkali metal hydrides, e.g. Sodium hydride. Triethylamine, pyridine and potassium carbonate are preferably used.
  • suitable solvents are chlorinated hydrocarbons, such as methylene chloride, 1,2-dichloroethane, aromatic hydrocarbons, for example toluene, xylene, chlorobenzene, ethers, such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran, dioxane, polar aprotic solvents, such as acetonitrile, dimethylformamide, Dimethyl sulfoxide, or esters such as ethyl acetate, or overall ⁇ mix of these.
  • chlorinated hydrocarbons such as methylene chloride, 1,2-dichloroethane
  • aromatic hydrocarbons for example toluene, xylene, chlorobenzene
  • ethers such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran, dioxane
  • polar aprotic solvents such as acetonitrile,
  • reaction temperature is in the range from 0 ° C. to the boiling point of the reaction mixture.
  • heterocyclic or heteroaromatic group can be partially or completely halogenated and / or can be substituted by R 5 ,
  • the compounds of formula I according to the invention are to be emphasized, the group Het being a five- or six-membered, partially or completely saturated heterocyclic or a five- or six-membered heteroaromatic group having up to three heteroatoms selected from the group consisting of nitrogen, oxygen or sulfur , wherein the named heterocyclic or heteroaromatic group can be partially or completely halogenated and / or substituted by R 5 ;
  • R 5 is hydrogen, hydroxy, mercapto, amino, cyano, nitro, formyl, C ⁇ -C 4 -alkylamino, C ⁇ -C 4 -dialkylamino, C ⁇ -C-alkoxycarbonyl, C ⁇ -C-alkylcarbonyl, C ⁇ -C 4 -alkylcarbonyloxy , C ⁇ -C-alkyl, C ⁇ -C -haloalkyl, C ⁇ -C 4 -alkylthio, C ⁇ -C 4 -haloalkylthio, C ⁇ -C 4 -alkoxy, C ⁇ -C 4 -halo-aikoxy, the alkyl radicals in all Cases can each be substituted by one or more of the following radicals: Cyano, formyl, C ⁇ -C 4 -alkylamino, C ⁇ -C 4 -dialkylamino, C ⁇ -C 4 -alkoxycarbonyl, C ⁇ -C 4 -alkylcarbonyl,
  • the organic molecule parts mentioned for the substituents R 1 - R 12 or as residues on phenyl, hetaryl and heterocyclyl rings represent collective terms for individual lists of the individual group members.
  • halogenated substituents preferably carry one to five identical or different halogen atoms. Halogen is fluorine, chlorine, bromine or iodine.
  • C ⁇ -C-alkyl as well as the alkyl parts of C ⁇ -C 4 -alkylcarbonyl: methyl, ethyl, n-propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1, 1-dimethylethyl;
  • C ⁇ -C 5 alkyl and the alkyl parts of C ⁇ -C 3 alkoxy-C -C 6 alkyl and C ⁇ -C 6 alkylcarbonyl: C ⁇ -C 4 alkyl, as mentioned above, and pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2, 2-dimethylpropyl, 1-ethylpropyl, hexyl,
  • C ⁇ -C 4 haloalkyl a C ⁇ -C 4 ⁇ alkyl radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, that is, for. B. chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2, 2-difluoroethyl, 2, 2, 2- Trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2, 2-difluoroethyl, 2, 2-dichloro-2-fluoroethyl, 2, 2, 2-trichloroethyl, pentafluoroethyl, 2-fluoroprop
  • C ⁇ -C 6 -alkoxy and the alkoxy parts of C ⁇ -C 6 -alkoxy-C ⁇ -C 6 -alkyl, C ⁇ -C 6 -alkoxy-C -C 6 -alkyl, C -C 4 -alkoxy- xy- C 2 -C 6 alkoxycarbonyl and C ⁇ -C 6 alkoxycarbonyl: C -C 4 alkoxy as mentioned above, and pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methoxylbutoxy, 1, 1-dimethylpropoxy,
  • 1,2-dirnethylpropoxy 2, 2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1, 1-dimethylbutoxy, 1, 2-dimethylbutoxy, 1, 3- Dimethylbutoxy, 2, 2-dimethylbutoxy, 2, 3-dimethylbutoxy, 3, 3-dimethylbutoxy, 1-ethylbutoxy, 2- ⁇ thylbutoxy, 1,1,2-trimethylpropoxy, 1, 2, 2-trimethylpropoxy, 1-ethyl- l-methyl propoxy and l-ethyl-2-methyl propoxy;
  • C ⁇ -C 4 haloalkoxy a C ⁇ -C 4 alkoxy radical as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, that is, for.
  • Ci-C ß- alkylsulfonyl C ⁇ -C 4 -alkylsulfonyl as mentioned above, and pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 2, 2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl Dimethylpropylsulfony, 1, 2-dimethylpropyl
  • C ⁇ -C 6 haloalkylsulfonyl a C ⁇ -C 6 alkylsulfonyl radical as mentioned above, which is partially or completely by
  • Fluorine, chlorine, bromine and / or iodine is substituted, ie fluoromethylsulfonyl, difluoromethylslfonyl, trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, 2-fluoroethylisulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-sulfonyl, 2 Difluoroethylsulfonyl,
  • C ⁇ -C 4 alkyliminooxy methyliminooxy, ethyliminooxy, 1-propyliminooxy, 2-propyliminooxy, 1-butyliminooxy and 2- butyliminooxyox
  • C 3 -C 6 alkenyl prop-1-en-l-yl, prop-2-en-l-yl, 1-methyl-ethenyl, buten-1-yl, buten-2-yl, buten-3- yl, 1-methyl-prop-1-en-l-yl, 2-methyl-prop-l-en-l-yl, l-methyl-prop-2-en- 1-yl, 2-methyl-prop- 2-en-l-yl, penten-1-yl, penten-2-yl, penten-3-yl, penten-4-yl, 1-methyl-but-1-en-l-yl, 2-methyl but-1-en-l-yl, 3-methyl-but-l-en-l-yl, 1-me yl-but-2-en-l-yl, 2-methyl-but-2-en-l -yl, 3-methyl- but-2-en-l-yl, 1-methyl-but-3-en-l-yl, 2-methyl-but-3-en-l-yl, 3-methyl-
  • C 2 -C 6 alkenyl C 3 -Cg alkenyl as mentioned above, and ethenyl;
  • C 3 -C 6 alkynyl prop-1-in-1-yl, prop-2-in-1-yl, but-1-in-1-yl, but-1-in-3-yl, but- l-in-4-yl, but-2-in-l-yl, pent-1-in-l-yl, pent-l-in-3-yl, pent-l-in-4-yl, pent l-in-5-yl, pent-2-in-l-yl, pent-2-in-4-yl, pent-2-in-5-yl, 3-methyl-but-l-in-3- yl, 3-methyl-but-l-in-4-yl, hex-1-in-l-yl, hex-l-in-3-yl, hex-l-in-4-yl, hex-l- in-5-yl, hex-1-in-6-yl, hex-2-in-1-yl, hex-2-in-4-yl, hex
  • C 2 -C 6 alkynyl C 3 -Ce alkynyl, as mentioned above, and ethynyl:
  • C -C6 cycloalkyl cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl
  • C 6 -C 6 -cycloalkenyl cyclobuten-1-yl, cyclobuten-3-yl, cyclopenten-1-yl, cyclopenten-3-yl, cyclopenten-4-yl, cyclohexen-1-yl, cyclohexen-3 -yl and cyclohexen-4-yl
  • C 6 -C 6 -cycloalkenyl cyclobuten-1-yl, cyclobuten-3-yl, cyclopenten-1-yl, cyclopenten-3-yl, cyclopenten-4-yl, cyclohexen-1-yl, cyclohexen-3 -yl and cyclohexen-4-yl
  • Heterocyclyl, and also the heteroclyl radicals in heterocyclyloxy three- to seven-membered, saturated or partially unsaturated mono- or polycyclic heterocycles which contain one to three heteroatoms selected from a group consisting of oxygen, nitrogen and sulfur, such as oxiranyl, 2-tetrahydrofuranyl, 3- Tetrahydrofuranyl, 2-tetrahydro-thienyl, 3-tetrahydrothienyl, 2-pyrrolidinyI, 3-pyrroiidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-isothiazolidinyl 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidiny
  • All phenyl, hetaryl and heterocyclyl rings are preferably unsubstituted or carry one to three halogen atoms and / or one or two radicals from the following group: nitro, cyano, methyl, trifluoromethyl, methoxy, trifluoromethoxy or methoxycarbonyl.
  • the variables preferably have the following meanings, in each case individually or in combination: R 1 nitro, halogen, cyano, rhodano, Cx-Cg-alkyl, C ⁇ -Cg-halogeno-alkyl, C ⁇ -C 6 -alkoxy-C ⁇ -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, -OR 3 or -S (0) n R 3 ; particularly preferably nitro, halogen such as fluorine, chlorine or bromine, C ⁇ -C 6 haloalkyl, -OR 3 or -S0 2 R 3 ;
  • R 2 is hydrogen, nitro, halogen, cyano, rhodano, Ci-C ⁇ -alkyl, C ⁇ -C 6 -haloalkyl, C ⁇ -C 6 -alkoxy-Ci-C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 - C 6 alkynyl, -OR 3 or -S (0) n R 3 ; particularly preferably hydrogen, nitro, halogen such as fluorine, chlorine or bromine, C ⁇ -Cg-alkyl, C -C 6 haloalkyl, -OR 3 or -S0 2 R 3 ;
  • R 3 is hydrogen, C ⁇ -C 6 alkyl, C ⁇ -C 6 haloalkyl, C 2 -Cg alkenyl, C 2 -Cg alyl, phenyl or Pher_yl-C ⁇ -Cg-alkyl; particularly preferably hydrogen, C ⁇ -C 4 alkyl, C ⁇ -C haloalkyl, C 2 -C 3 alkenyl, C 2 -C 3 alkynyl or phenyl; wherein the alkyl radicals mentioned can be partially or completely halogenated and / or can carry one to three of the following groups:
  • X 1 is a straight-chain or branched C ⁇ -C 4 alkylene, a C 2 -C 4 alkenylene or a C 2 -C 4 alkynylene chain, particularly preferably an ethylene, propylene, propenylene or propinylene chain, which is represented by a Heteroatom selected from the group
  • alkylene, alkenylene or alkynylene radicals mentioned can be partially halogenated and / or can carry one to three of the following groups:
  • R 4 is hydrogen, C 1 -C 6 -alkyl or C ⁇ -C 6 -haloalkyl; particularly preferably hydrogen, methyl, ethyl or trifluoromethyl;
  • R 5 is hydrogen, hydroxy, mercapto, amino, cyano, nitro, formyl, C ⁇ -C 4 -alkylamino, C ⁇ -C 4 -dialkyiamino, C ⁇ -C 4 -alkoxycarbonyl, C ⁇ -C 4 -alkylcarbonyl, C ⁇ -C -alkylcarbonyloxy, C ⁇ -C 4 -alkyl, C ⁇ -C 4 -haloalkyl, C ⁇ -C 4 -alkylthio, C ⁇ -C 4 -haloalkylthio, C ⁇ -C 4 -alkoxy, C ⁇ -C 4 -haloalkoxy, the alkyl radicals in each case by one or more of the following groups may be substituted:
  • R 6 , R 7 , R 9 , R 11 are hydrogen or C x -C alkyl; particularly preferably hydrogen, methyl or ethyl;
  • R S is hydrogen, C ⁇ -C alkyl, C 3 -C 4 cycloalkyl, the latter two groups optionally being able to carry one to three of the following substituents: halogen, C ⁇ -C 4 alkoxy or C ⁇ -C alkylthio;
  • R 10 is hydrogen, C ⁇ -C 4 alkyl or C ⁇ -C 4 alkoxycarbonyl; particularly preferably hydrogen, methyl or methoxycarbonyl.
  • R 8 and R 11 form a ⁇ bond, so that a double bond system is formed.
  • the compounds of the formula Ia are particularly preferred, where R 1 is bonded in position 2 and R 2 is bonded in position 4 of the phenyl ring.
  • Group can be partially or completely halogenated and / or substituted by R 5 ;
  • the compounds of formula la according to the invention are extremely preferred, in which the substituents R 1 , R 2 and X 1 have the meaning given above and Het for a five- or six-membered, partially or completely saturated, heterocyclic group or a five- or six-membered heteroaromatic group with up to three heteroatoms, particularly preferably with one or two heteroatoms selected from the following three groups:
  • heterocyclic or heteroaromatic group may be partially or completely halogenated and / or may be substituted by R 5 ;
  • the bridge link X 1 is linked at the left end to the central phenyl ring and at the right end to Het.
  • Methylsulfonyl, R 6 , R 7 , R 8 , R 9 , R 10 and R : ⁇ is hydrogen and the substituents X 1 and Het correspond to one row of Table A for each individual compound.
  • Table 6 Compounds 6.1-6.920 compounds of the general formula Ib, in which R 1 is methyl, R 2 trifluoromethyl, R 6 , R 7 , R 8 , R 9 , R 10 and R 11 is hydrogen and the substituents X 1 and Het correspond to one row of Table A for each individual compound.
  • Methyls lfonyl, R 6 , R 7 , R 10 and R 11 is hydrogen, R 8 and R 9 is methyl and the substituents X 1 and Het correspond to one row of Table A for each individual compound.
  • Table 12 Compounds 12.1-12.920 compounds of the general formula Ib, in which R 1 is methyl, R 2 trifluoromethyl, R 6 , R 7 , R 10 and R 11 is hydrogen, R 8 and R 9 is methyl and the substituents X 1 and Het correspond to one row of Table A for each individual connection.
  • Methylsulfonyl, R 6 , R 7 , R 8 and R 9 is hydrogen, R 10 and R 11 is methyl and the substituents ⁇ i and Het correspond to one row of Table A for each individual compound.
  • Table 25 Compounds 25.1-25.920 compounds of the general formula Ib, in which R 1 is methylsulfonyl, R 6 , R 7 , R 8 , R i ° and R 11 is hydrogen, R 9 is methyl, the substituents X 1 and Het for each individual Connection correspond to one row of Table A each.
  • Chlorine, R 6 , R 7 , R 9 and R 10 are hydrogen, R 8 and R 11 together form a methylene group and the substituents X x and Het correspond to one row of Table A for each individual compound.
  • the compounds I and their agriculturally useful salts are suitable - both as isomer mixtures and in the form of the pure isomers - as herbicides.
  • the herbicidal compositions containing I control vegetation very well on non-cultivated areas, particularly when high amounts are applied. In crops such as wheat, rice, corn, soybeans and cotton, they act against weeds and grass weeds without significantly damaging the crop plants. This effect occurs especially at low application rates.
  • the compounds I or compositions containing them can also be used in a further number of crop plants for eliminating undesired plants.
  • the following crops are considered, for example:
  • the compounds I can also be used in crops which are tolerant to the action of herbicides by breeding, including genetic engineering methods.
  • the herbicidal compositions or the active compounds can be applied pre- or post-emergence. If the active ingredients are less compatible with certain crop plants, application techniques can be used in which the herbicidal compositions are sprayed with the aid of sprayers in such a way that the leaves of the sensitive crop plants are not hit as far as possible, while the active ingredients are applied to the leaves of undesirable plants growing below them or the uncovered floor area (post directed, lay-by).
  • the compounds I or the herbicidal compositions comprising them can be sprayed or atomized, for example in the form of directly sprayable aqueous solutions, powders, suspensions, including high-strength aqueous, oily or other suspensions or dispersions, emulsions, old-dispersions, pastes, dusts, sprays or granules , Dusting, scattering or pouring.
  • the application forms depend on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, also coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, alkylated benzenes or their derivatives, alcohols such as methanol, ethanol, propanol, butanol, cyclohexanol, ketones such as cyclohexanone or strongly polar solvents, e.g. Amines such as N-methylpyrrolidone or water.
  • mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, also coal tar oils and oils of vegetable or animal origin
  • aliphatic, cyclic and aromatic hydrocarbons e.g. Paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, alkylated
  • Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water.
  • the substituted 2-benzoylcyclohexane-1, 3-diones as such or dissolved in an oil or solvent can be homogenized in water using wetting agents, adhesives, dispersants or emulsifiers.
  • concentrates consisting of an active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil, which are suitable for dilution with water.
  • the surface-active substances are the alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic acids, for example lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa- , Hepta and octadecanols and fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl or nonylphenol ether, alkylphenyl, aryl pheny
  • Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
  • Granules e.g. Coated, impregnated and homogeneous granules can be produced by binding the active ingredients to solid carriers.
  • Solid carriers are mineral earths such as silica, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, Ammonium nitrate, ureas and vegetable products such as corn flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
  • mineral earths such as silica, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium s
  • the concentration of the active ingredients I in the ready-to-use preparations can be varied over a wide range.
  • the formulations generally contain 0.001 to 98% by weight, preferably 0.01 to 95% by weight, of at least one active ingredient.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).
  • the compounds I according to the invention can be formulated, for example, as follows:
  • V 3 parts by weight of compound I are mixed with 97 parts by weight of finely divided kaolin. In this way, a dusting agent is obtained which contains 3% by weight of the active ingredient.
  • the substituted 2-benzoylcyclohexane-1,3-diones can be mixed with numerous representatives of other herbicidal or growth-regulating active compound groups and applied together.
  • 1, 2, 4-thiadiazoles, 1, 3, 4 -thiadiazoles, amides, aminophosphoric acid and their derivatives, aminotriazoles, anilides, (het) -aryloxyalkanoic acid and their derivatives, benzoic acid and their derivatives, benzothiadiazone come as mixing partners , 2-aroyl-1, 3 -cyclohexane ione, hetaryl aryl ketones, benzyl isooxazolidinones, meta-CF-phenyl derivatives, carbamates, quinoline carboxylic acid and their derivatives, chloroacetanilides, cyclohexane-1, 3-dione derivatives, diazines, dichloropropionic acid and their derivatives
  • the application rates of active ingredient are 0.001 to 3.0, preferably 0.01 to 1.0 kg / ha of active substance (as), depending on the control target, the season, the target plants and the growth stage.
  • Step b 2-Chloro-3 - [(1 -methylpyrazole -5 -yl) oxymethyl] -4 -methylsulfonyl -benzoic acid methyl ester
  • Step c 2 -Chlor -3 - [(1 -methylpyrazole -5 -yl) oxymethyl] -4 -methylsulfonyl -benzoic acid
  • Step d ⁇ 2-Chloro-3- [(1 -methylpyrazole-5-yl) oxymethyl] -4-methysulfonylphenyl ⁇ - ⁇ 5, 5-dimethyl-1,3-dioxocyclohex-2-yl ⁇ metha - non 45 1.0 g (2.9 mmol) 2-chloro-3 - [(1-methylpyrazole-5-yl) oxymethyl] -4-methylsulfonyl-benzoic acid, 0.4 g (2.9 mmol) dimedone and 0.72 g of N, N-dicyclohexylcarbodiimide are heated in 40 ml of acetonitrile at 40 ° C. for 4 h.
  • the active ingredients suspended or emulsified in water were applied directly after sowing using finely distributing nozzles.
  • the tubes were lightly sprinkled to promote germination and growth, and then covered with transparent plastic hoods until the plants had grown. This cover caused the test plants to germinate evenly, unless this was affected by the active compounds.
  • test plants were first grown to a height of 3 to 15 cm, depending on the growth habit, and then treated with the active ingredients suspended or emulsified in water.
  • the test plants were either sown directly and grown in the same containers or they were first grown separately as seedlings and transplanted into the test containers a few days before the treatment.
  • the plants were kept at temperatures of 10 - 25 ° C or 20 - 35 ° C depending on the species.
  • the trial period lasted 2 to 4 weeks. During this time, the plants were cared for and their response to each treatment was evaluated.
  • Evaluation was carried out on a scale from 0 to 100. 100 means no emergence of the plants or complete destruction of at least the aerial parts and 0 means no damage or normal growth.

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  • Chemical & Material Sciences (AREA)
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  • Life Sciences & Earth Sciences (AREA)
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  • Wood Science & Technology (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
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  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract

La présente invention concerne 2-benzoyl-cyclohexane-1,3-dione de formule (I), dans laquelle les substituents ont la signification indiquée dans la description, leurs sels utilisables sur le plan agricole, leur production et les produits intermédiaires utilisés pour obtenir les composés de formule (I), les agents contenant lesdits composés, l'utilisation de la formule (I), ainsi que les agents contenant lesdits composés pour la lutte antiparasitaire.
EP98942611A 1997-08-07 1998-08-05 2-benzoyl-cylcohexane-1,3-dione a usage d'herbicide Withdrawn EP1001938A1 (fr)

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EP10184196A EP2343276A1 (fr) 1997-08-07 1998-08-05 2-Benzoyl-cyclohexane-1,3-diones comme herbicides

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DE19734164 1997-08-07
DE19734164 1997-08-07
PCT/EP1998/004634 WO1999010327A1 (fr) 1997-08-07 1998-08-05 2-benzoyl-cylcohexane-1,3-dione a usage d'herbicide

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DE10136449A1 (de) * 2001-05-09 2002-11-14 Bayer Ag Substituierte Arylketone
RU2302411C2 (ru) * 2001-05-09 2007-07-10 Байер Кропсайенс Аг Замещенные арилкетоны и гербицидное средство на их основе
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CN105601548A (zh) * 2016-01-18 2016-05-25 黑龙江大学 苯甲酰类化合物、含有该化合物的组合物及其应用
CN108264484A (zh) * 2016-12-30 2018-07-10 浙江省化工研究院有限公司 一种带醚结构的取代的苯基酮类化合物、其制备方法及应用
CN112142671B (zh) * 2019-06-27 2024-01-16 东莞市东阳光农药研发有限公司 取代的苯甲酰-吡唑类化合物及其在农业中的应用
CN112174889B (zh) * 2019-07-03 2024-01-16 东莞市东阳光农药研发有限公司 取代的苯甲酰类化合物及其在农业中的应用
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AU9068498A (en) 1999-03-16
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JP2001514171A (ja) 2001-09-11
JP2011016803A (ja) 2011-01-27
US6432881B1 (en) 2002-08-13
EP2343276A1 (fr) 2011-07-13
JP4592183B2 (ja) 2010-12-01
CA2298462C (fr) 2008-02-12
AR016595A1 (es) 2001-07-25
ZA987057B (en) 2000-02-07

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