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WO2001000607A1 - Derives cyclohexenone d'acide benzoique en tant qu'herbicides - Google Patents

Derives cyclohexenone d'acide benzoique en tant qu'herbicides Download PDF

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Publication number
WO2001000607A1
WO2001000607A1 PCT/EP2000/005790 EP0005790W WO0100607A1 WO 2001000607 A1 WO2001000607 A1 WO 2001000607A1 EP 0005790 W EP0005790 W EP 0005790W WO 0100607 A1 WO0100607 A1 WO 0100607A1
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alkyl
alkoxy
phenyl
aminocarbonyl
methyl
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PCT/EP2000/005790
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German (de)
English (en)
Inventor
Klaus Langemann
Ernst Baumann
Wolfgang Von Deyn
Steffen Kudis
Guido Mayer
Ulf Misslitz
Ulf Neidlein
Matthias Witschel
Norbert Götz
Martina Otten
Karl-Otto Westphalen
Helmut Walter
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Basf Aktiengesellschaft
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Priority to AU59771/00A priority Critical patent/AU5977100A/en
Publication of WO2001000607A1 publication Critical patent/WO2001000607A1/fr

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    • 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
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/12—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings condensed with a carbocyclic ring
    • 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
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A01N43/38—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings condensed with carbocyclic rings
    • 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
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/72—Benzo[c]thiophenes; Hydrogenated benzo[c]thiophenes

Definitions

  • the present invention relates to cyclohexenone derivatives of bicyclic benzoic acids which have a fused, saturated heterocycle in the 2,3-position, processes for the preparation of such cyclohexenone derivatives, agents which contain such compounds, and the use of the cyclohexenone derivatives or agents containing them for controlling harmful plants.
  • WO 97/09324 discloses cyclohexane-1,3-diones with herbicidal action which have a benzo-condensed position in the 2 position
  • Sulfur heterocycle e.g. have a thiochroman or a benzodihydrothiophene radical which is bonded via a carbonyl group.
  • Herbicides are known from WO 97/08164 which have a cyclohexenone radical which is substituted in the 2-position by a bicyclic arylcarbonyl radical.
  • arylcarbonyl radicals are benzocondensed lactones such as benzfuranone, benzopyranone, lactams such as benzopyrrolidone and benzopyrimidone, 5 2,3-benzo-4, 5-dihydrothiophene dioxide and 2,3-benzo-4,5,6, 7-tetra - called hydrothiepindioxid.
  • the present invention is therefore based on the object of providing new compounds with herbicidal activity which preferably have a higher activity than the herbicidal substances of the prior art and / or a better selectivity towards harmful plants.
  • the present invention relates to cyclohexenone derivatives 5 of bicyclic benzoic acids of the general formula I,
  • X represents 0, S, SO, S0 2 , NR 1 or N-NR 1 R 17 ,
  • R 1 is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylsulfonyl, C 1 -C 6 - Haloalkyl sulfonyl, C 1 -C 6 alkoxy-C 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl, C 1 -C 6 alkylcarbonyl-C 1 -C 6 - alkyl, C 1 -C 6 alkylcarbonyl-C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkylcarbonyloxy-C 1 -C 6 alkyl,
  • heterocyclyl heterocyclylsulfonyl, heterocyclylcarbonyl, heterocyclyl-C 1 -C 6 -alkyl, heterocyclylcarbonyl-C 1 -C 6 -alkyl or heterocyclylcarbonyloxy-C 1 -C 6 -alkyl
  • phenyl, heterocyclyl and cycloalkyl radicals of the aforementioned groups optionally one, two, three or four substituents selected from C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 alkylcarbonyl, C 1 -C 4 -haloalkylcarbonyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 nalkylsulfonyl -Haloge-, nitro, hydroxy or cyano wear and / or can be partially or fully halogenated;
  • R 2 for halogen, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 alkylsulfonyl or C 1 - C 6 haloalkylsulfonyl;
  • R 3 represents hydrogen, halogen, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl, and
  • R 5 , R 9 independently of one another are hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxycarbonyl;
  • R 6 , R 8 , R 10 independently of one another are hydrogen or C 1 -C 4 alkyl
  • R 7 is hydrogen, halogen, hydroxy, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, di- (C 1 -C 6 alkoxy) methyl, (C 1 -C 6 alkoxy) - (C 1 -C 6 alkylthio) methyl, di (C 1 -C 6 alkylthio) methyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylthio, C 1 - C 6 haloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 alkylsulfonyl, C 1 -C 6 haloalkylsulfonyl, C 1 -C 6 alkoxycarbonyl, C 1 -C 6 haloalkoxycarbonyl;
  • R 6 and R 10 together form a C 1 -C 4 alkyl chain which can carry one or two radicals from the following group: halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 alkoxycarbonyl; or
  • R 7 and R 8 together form an -O- (CH 2 ) p -O-, -O- (CH 2 ) p -S-,
  • R 7 and R 8 together with the carbon to which they are attached form a carbonyl group
  • R 11 is C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl,
  • R 12 is C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl or
  • C 3 -C 6 cycloalkyl where the four radicals mentioned can be partially or completely halogenated and / or can carry one, two or three of the following groups: cyano, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy , C 1 -C 4 alkylthio, C 1 -C 4 haloalkylthio, C 1 -C 4 alkylcarbonyl, C 1 -C 4 alkoxycarbonyl or C 1 -C 4 haloalkoxycarbonyl,
  • R 13 , R 14 independently of one another are hydrogen, hydroxy, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylthio, phenyl, phenyl-C 1 -C 4 -alkyl or phenoxy, where the three latter substituents can be partially or completely halogenated and / or can carry one, two or three of the following radicals: nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 - Alkoxy, C 1 -C 4 haloalkoxy or C 1 -C 4 alkoxycarbonyl;
  • R 15 is hydrogen, C 1 -C 6 alkyl, C 3 -C 6 alkenyl,
  • R 16 , R 17 independently of one another are hydrogen, C 1 -C 6 alkyl, C 3 -C 6 alkenyl or C 3 -C 6 alkynyl;
  • herbicidal compositions which contain cyclohexenone derivatives of the formula I and have a very good herbicidal action.
  • the compounds of the formula I can contain one or more centers of chirality and are then present as enantiomers or mixtures of diastereomers.
  • the invention relates 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. Generally they come
  • the cations used are, in particular, ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium and magnesium, and of the transition metals, preferably manganese, copper, zinc and iron, and ammonium, with one to four hydrogen atoms here if desired through C 1 -C 4 -alkyl, hydroxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, hydroxy-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, Phenyl or benzyl can be replaced, preferably ammonium, dimethylammonium, diisopropylammonium, tetramethylammonium, tetrabutylammonium, 2- (2
  • 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 1 -C 4 -alkane acids, preferably formate, acetate Propionate and butyrate.
  • Ilb also represent the tautomeric forms Ilb ', Ilb''andIlb'''.
  • N alkyl — N — heterocyclylaminocarbonyl, phenylalkyl, heterocyclylalkyl, phenylcarbonylalkyl, heterocyclylcarbonylalkyl, alkoxyalkoxycarbonyl,
  • N — alkynyl — N — alkoxyaminocarbonyl, alkenyl, alkynyl, haloalkenyl, haloalkynyl, alkenyloxy, alkynyloxy, alkanediyl, alkenediyl, alkadienediyl or alkynediyl parts can be straight-chain or branched.
  • halogenated substituents preferably carry one to five same or different halogen atoms. Halogen is fluorine, chlorine, bromine or iodine.
  • C 1 -C 4 alkyl for example methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl or 1, 1-dimethylethyl;
  • C 1 -C 6 alkyl and the alkyl parts of C 1 -C 6 alkylamino, di- (C 1 -C 6 alkyl) amino, N- (C 1 -C 6 alkoxy) -N- (C 1 -C 6 alkyl) amino, N (C 1 -C 6 alkoxy) -N- (C 1 -C 6 alkyl) aminocarbonyl, N- (C 3 -C 6 alkenyl) -N- (C 1 -C 6 alkyl) aminocarbonyl, N- (C 3 -C 6 alkynyl) —N— (C 1 -C 6 alkyl) aminocarbonyl, N— (C 1 -C 6 alkyl) —N— phenylaminocarbonyl, N— (C 1 -C 6 alkyl) —N — heterocyclylaminocarbonyl: C 1 -C 4 alkyl, as mentioned above, and for example pentyl, 1
  • C 1 -C 4 haloalkyl a C 1 -C 4 alkyl radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example 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-fluoropropyl, 3-fluoropropyl,
  • C 1 -C 6 haloalkyl and also the haloalkyl parts of NC 1 -C 6 haloalkylamino: C 1 -C 4 haloalkyl, as mentioned above, and, for example, 5-fluoropentyl,
  • C 1 -C 4 -alkoxy for example methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or
  • C 1 -C 4 haloalkoxy a C 1 -C 4 alkoxy radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy , 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2, 2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2, 2-difluoroethoxy, 2 , 2-Di-chloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromoprop
  • C 1 -C 6 haloalkoxy C 1 -C 4 haloalkoxy, as mentioned above, and for example 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluoroexoxy;
  • C 1 -C 4 alkylthio (C 1 -C 4 alkylsulfanyl: C 1 -C 4 alkyl-S-): for example methylthio, ethylthio, propylthio, 1-methylethylthio,
  • C 1 -C 6 alkylthio and the alkylthio parts of C 1 -C 6 alkylthiocarbonyl: C 1 -C 4 alkylthio, as mentioned above, and for example pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2 , 2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1, 1-dimethylpropylthio, 1, 2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-ethylpentylthio, 4-methylpentylthio, 1, 1-dimethylbutylthiobutyl, 1, 2 , 1, 3-dimethylbutylthio, 2, 2-dimethylbutylthio, 2, 3-dimethylbutylthio, 3, 3-dimethylbutylthio, 1-ethylbutylthio, 2-eth
  • C 1 -C 4 -haloalkylthio a C 1 -C 4 -alkylthio radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio , 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2, 2-difluoroethylthio, 2, 2, 2-trifluoroethylthio, 2, 2, 2-trichloroethylthio,
  • 2-chloro-2-fluoroethylthio 2-chloro-2, 2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, pentafluoroethylthio, 2-fluoropropylthio, 3-fluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2-bromopropylthio, 3 — bromopropylthio, 2, 2 — difluoropropylthio, 2, 3 — difluoropropylthio,
  • C 1 -C 6 haloalkylthio C 1 -C 4 haloalkylthio, as mentioned above, and 5 — fluoropentylthio, 5 — chloropentylthio, 5 — bromopentylthio, 5 — iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio, 6-chlorohexylthio, 6-bromohexylthio, 6-iodohexylthio or dodecafluorohexylthio;
  • Butylsulfinyl 1-methylpropylsulfinyl, 2-methylpropylsulfinyl or 1, 1-dimethylethylsulfinyl;
  • C 1 -C 6 alkylsulfinyl C 1 -C 4 alkylsulfinyl, as mentioned above, and pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 2, 2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, 1, 1-dimethylpropylsulfinyl , 1,2-dimethylpropylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl,
  • 4-methylpentylsulfinyl 1, 1-dimethylbutylsulfinyl, 1, 2-dimethylbutylsulfinyl, 1, 3-dimethylbutylsulfinyl, 2, 2-dimethylbutylsulfinyl, 2, 3-dimethylbutylsulfinyl, 3, 3-dimethylbutylsulfinyl, 1-ethylbutylsulfyl, 1-ethylbutylsulfyl, 1, 2-trimethylpropylsulfinyl,
  • Fluorine, chlorine, bromine and / or iodine is substituted, e.g.
  • C 1 -C 6 haloalkylsulfinyl C 1 -C 4 haloalkylsulfinyl as mentioned above, as well as 5-fluoropentylsulfinyl, 5-chloropentylsulfinyl, 5-bromopentylsulfinyl, 5-iodopentylsulfinyl, undecafluoropentylsulfinyl, 6-fluorhexylsulfinyl, 6-chlorohexylsulfylsulfinyl , 6-iodohexylsulfinyl or dodecafluorohexylsulfinyl;
  • C 1 -C 6 alkylsulfonyl C 1 -C 4 alkylsulfonyl as mentioned above, and pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1, 1-dimethylpropylsulfonyl, 1, 2-dimethylpropylsulfonyl —Dimethylpropylsulfonyl, 1 — ethylpropylsulfonyl, hexylsulfonyl, 1 — methylpentylsulfonyl, 2 — methylpentylsulfonyl, 3 — methylpentylsulfonyl, 4— ethylpentylsulfonyl, 1, 1 — dimethylbutylsulfonyl, 1, 2-dimethylbutyl, 2-sulfylyl
  • C 1 -C 4 haloalkylsulfonyl a C 1 -C 4 alkylsulfonyl radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example fluoromethylsulfonyl, difluoromethylsulfonyl,
  • Trifluoromethylsulfonyl chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, 2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl, 2, 2-difluoroethylsulfonyl, 2, 2, 2-trifluoromethylsulfonyl, 2, 2-2-trifluoromethylsulfonyl 2-difluoroethylsulfonyl, 2,2-dichloro-2-fluoroethylsulfonyl,
  • 2,2,2-trichloroethylsulfonyl pentafluoroethylsulfonyl, 2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl, 2-chloropropylsulfonyl, 3-chloropropylsulfonyl, 2-bromopropylsulfonyl, 3-bromopropylsulfonyl, 2,2-propylsulphonylsulfonyl 2,3-dichloropropylsulfonyl, 3,3,3-trifluoropropylsulfonyl, 3,3,3-trichloropropylsulfonyl,
  • C 1 -C 6 haloalkylsulfonyl C 1 -C 4 haloalkylsulfonyl, as mentioned above, and 5-fluoropentylsulfonyl,
  • C 1 -C 6 alkylamino methylamino, ethylamino, propylamino, 1-methylethylamino, butylamino, 1-methylpropylamino, 2-methylpropylamino, 1, 1-dimethylethylamino, pentylamino, 1-methylbutylamino, 2-methylbutylamino, 3-methylbutylamino , 2-dimethylpropylamino, 1-ethylpropylamino, hexylamino, 1, 1-dimethylpropylamino, 1, 2-dimethylpropylamino, 1-methylpentylamino, 2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino, 1, 1-dimethylbutylaminobutylamino, 1, 2 , 1, 3-dimethylbutylamino, 2, 2-dimethylbutylamino, 2, 3-dimethylbutylamino, 3, 3-dimethylbutyla
  • N-methyl-N- (2-methylpropyl) amino N- (1, l-dimethylethyl) -N-methylamino, N-ethyl-N-propylamino,
  • Di- (C 1 -C 6 -alkyl) amino di- (C 1 -C 4 -alkyl) amino as mentioned above, and N, N-dipentylamino, N, N-dihexylamino, N-methyl-N-pentylamino, N-ethyl-N-pentylamino,
  • C 1 -C 4 alkylcarbonyl for example methylcarbonyl, ethylcarbonyl, propylcarbonyl, 1-methylethylcarbonyl, butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl or 1, 1-dimethylethylcarbonyl;
  • C 1 -C 4 haloalkylcarbonyl a C 1 -C 4 alkylcarbonyl radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example chloroacetyl, dichloroacetyl, trichloroacetyl, fluoroacetyl, difluoroacetyl , Trifluoroacetyl, chlorofluoroacetyl, dichlorofluoroacetyl, chlorodifluoroacetyl,
  • C 1 -C 6 haloalkylcarbonyl a C 1 -C 4 haloalkylcarbonyl radical as mentioned above, and 5-fluoropentylcarbonyl, 5-chloropentylcarbonyl, 5-bromopentylcarbonyl, perfluoropentylcarbonyl, 6-fluorhexylcarbonyl, 6-chlorohexylcarbonyl, 6-bromohexylcarbonyl or perfluorhexylcarbonyl;
  • C 1 -C 4 alkoxycarbonyl for example methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, 1-methylethoxycarbonyl, butoxycarbonyl, 1-methylpropoxycarbonyl, 2-methylpropoxycarbonyl or 1, 1-dimethylethoxycarbonyl;
  • C 1 -C 6 alkoxycarbonyl C 1 -C 4 alkoxycarbonyl, as mentioned above, and also, for example, pentoxycarbonyl, 1-methylbutoxycarbonyl,
  • C 1 -C 4 haloalkoxycarbonyl a C 1 -C 4 alkoxycarbonyl radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example fluo
  • 2,2,2-trichloroethoxycarbonyl pentafluoroethoxycarbonyl, 2-fluoropropoxycarbonyl, 3-fluoropropoxycarbonyl, 2-chloropropoxycarbonyl, 3-chloropropoxycarbonyl, 2-bromopropoxycarbonyl, 3-bromopropoxycarbonyl,
  • C 1 -C 6 haloalkoxycarbonyl a C 1 -C 4 haloalkoxycarbonyl radical as mentioned above, and 5-fluoropentoxycarbonyl, 5-chloropentoxycarbonyl, 5-bromopentoxycarbonyl, 6-fluorohexoxycarbonyl,
  • C 1 -C 4 alkyl carbonyloxy acetyloxy, ethylcarbonyloxy, propylcarbonyloxy, 1 — methylethylcarbonyloxy, butylcarbonyloxy, 1 — methylpropylcarbonyloxy,
  • C 1 -C 4 -alkylamino carbonyl for example methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl, 1-ethylethylaminocarbonyl, butylaminocarbonyl,
  • N, N-di- (1-methylethyl) aminocarbonyl N, N-dipropylaminocarbonyl, N, N-dibutylaminocarbonyl,
  • N-methyl-N-1-methylbutyl) aminocarbonyl N-methyl-N-2-methylbutyl) aminocarbonyl, N-methyl-N-3-methylbutyl) aminocarbonyl, N-methyl-N-2,2-dimethylpropyl ) —Aminocarbonyl, N-methyl-N-1-ethylpropyl) —aminocarbonyl,
  • N-ethyl-N-1-methylbutyl) -aminocarbonyl N-ethyl-N-2-methylbutyl) -aminocarbonyl, N-ethyl-N-3-methylbutyl) -aminocarbonyl, N-ethyl-N-2,2-dimethylpropyl ) —Aminocarbonyl, N-ethyl-N-1-ethylpropyl) —aminocarbonyl,
  • N-butyl-N-pentylaminocarbonyl N, N-dipentylaminocarbonyl, N-propyl-N-hexylaminocarbonyl, N-butyl-N-hexylaminocarbonyl, N-pentyl-hexylaminocarbonyl or N, N-dihexylaminocarbonyl;
  • N-methyl-N-1-methylbutyl) aminothiocarbonyl N-methyl-N-2-methylbutyl) aminothiocarbonyl, N-methyl-N-3-methylbutyl) aminothiocarbonyl, N-methyl-N-2, 2-dimethylpropy1 ) —Aminothiocarbonyl, N-methyl-N-1-ethylpropyl) —aminothiocarbonyl,
  • C 1 -C 6 hydroxyalkyl C 1 -C 6 alkyl substituted by one to three OH groups, for example hydroxymethyl, 1-hydroxyethyl, 2-hydroxyethyl, 1, 2-bishydroxyethyl, 1-hydroxypropyl, 2-hydroxypro - pyl, 3-hydroxypropyl, 4-hydroxybutyl, 2, 2-dimethyl-3-hydroxypropyl;
  • Phenyl-C 1 -C 6 alkyl substituted by a phenyl C 1 -C 6 -alkyl, for example benzyl, 1-phenylethyl and 2-phenylethyl, wherein the phenyl radical in the indicated manner may be partially or fully halogenated or one to three which may have substituents given above for phenyl;
  • Heterocyclyl-C 1 -C 6 -alkyl accordingly represents a C 1 -C 6 -alkyl substituted by a heterocyclyl radical
  • C 1 -C 6 alkoxy-C 1 -C 6 -alkyl C 1 -C 6 -alkoxy as mentioned above, substituted C 1 -C 6 alkyl, eg methoxymethyl,
  • C 1 -C 6 alkoxy-C 1 -C 6 alkoxy substituted by C 1 -C 6 alkoxy, as mentioned above C 1 -C 6 alkoxy, for example for
  • C 2 -C 6 alkenyl and the alkenyl portions of C 2 -C 6 alkenylcarbonyl, phenyl C 2 -C 6 alkenylcarbonyl and heterocyclyl C 2 -C 6 alkenylcarbonyl: C 3 -C 6 alkenyl as above called, as well as ethenyl;
  • C 3 -C 6 haloalkenyl a C 3 -C 6 alkenyl radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example 2-chloroallyl, 3-chloroallyl, 2 , 3-dichlorallyl, 3, 3-dichlorallyl,
  • C -C 6 alkynylcarbonyl C 3 -C 6 alkynyl as mentioned above and ethynyl;
  • C 3 -C 6 haloalkynyl a C 3 -C 6 alkynyl radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, that is to say, for example, 1,1-difluoroprop-2 -In-1-yl, 3-iodine-prop-2-in-1-yl, 4-fluorobut-2-in-l-yl, 4-chlorobut-2-in-l-yl, 1, 1-difluorobut —2-in-1-yl, 4-iodine-but-3-in-1-yl, 5-fluoropent — 3-in-1-yl, 5-iodine-pent-4-in-1-yl, 6 —Fluorine-hex-4-in-1-yl or 6-iodine-hex-5-in-1-yl;
  • C 1 -C 6 alkanediyl methanediyl, ethane-1, 1-diyl, ethane-1, 2-diyl, propane-1, 1-diyl, propane-1, 2-diyl, propane-l, 3-diyl, Propane-2, -diyl, butane-1, 1-diyl, butane-1, 2-diyl, butane-l, 3-diyl, butane-1, 4-diyl, 2-methyl-propane-l, 3-diyl , 2-methyl-propane-l, 2-diyl, 2-methyl-propane-l, 1-diyl, 1-methyl-propane-l, 2-diyl, l-methyl-propane-2, 2-diyl, 1 -Methyl-propane-l, 1-diyl, pentane-1, 1-diyl, pentane-1, 2-diyl, pentan
  • C 3 -C 6 cycloalkyl as well as the cycloalkyl parts of C 3 -C 6 cycloalkylamino and C 3 -C 6 cycloalkylcarbonyl: for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;
  • heterocyclyl and Heterocyclylmaschine of heterocyclyloxy, heterocyclylcarbonyl, heterocyclyl-C 1 -C 4 -alkyl, heterocyclyl-C 1 -C 6 alkyl, heterocyclylsulfonyl or Heterocyclyloxysulfonyl, heterocyclyloxycarbonyl, Heterocyclyloxythiocarbonyl, heterocyclyl-C 2 -C 6 alkenylcarbonyl, heterocyclylcarbonyl C 1 -C 6 alkyl, N— (C 1 -C 6 alkyl) —N— (heterocyclyl) aminocarbonyl, heterocyclylaminocarbonyl: a saturated, partially saturated or unsaturated 5- or 6- membered heterocyclic ring which comprises a contains two, three or four identical or different heteroatoms, selected from the following group: oxygen, sulfur or nitrogen, for example contains C-linked 5-membered rings such as:
  • Tetrahydropyran-4-yl piperidine-2-yl, piperidine-3-yl, piperidine-4-yl, tetrahydrothiopyran-2-yl, tetrahydrothiopyran-3-yl, tetrahydrothiopyran-4-yl, 2H-3, 4-dihydropyran 6-yl, 2H-3,4, -dihydropyran-5-yl, 2H-3,4, -dihydropyran-4-yl, 2H-3,4, -dihydropyran-3-yl, 2H-3,4, -dihydropyran-2- yl, 2H-3,4-dihydropyran-6-yl, 2H-3,4, -dihydrothiopyran-5-yl, 2H-3,4, -dihydrothiopyran-4-yl, 2H-3,4, -dihydropyran-3-yl, 2H-3,4-dihydropyran
  • 1,4-dihydropyrimidine-4-yl 1,4-dihydropyrimidine-5-yl, 1,4-dihydropyrimidine-6-y dihydropyrimidine-2-yl, 3,4-dihydropyrimidine-4-yl, 3,4-dihydropyrimidine-5-yl, 3,4-dihydropyrimidine-6-yl, pyridazine-3-yl, pyridazine-4-yl, pyrimidine-2-yl, pyrimidine- 4-yl, pyrimidine-5-yl, pyrazine-2-yl, 1,3,5-triazine-2-yl, 1,2, 4-riazine-3-yl, 1, 2, 4-triazine-5 - yl, 1,2, 4-triazine-6-yl or 1, 2, 4, 5-tetrazine-3-yl;
  • N-linked 5-membered rings such as:
  • N-linked 6-membered rings such as:
  • N-linked cyclic imides such as:
  • a bicyclic ring system can be formed with a fused-on phenyl ring or with a C 3 -C 6 carbocycle or a further 5- to 6-membered heterocycle, and
  • variables X, R 1 , R 2 , R 3 and R 17 preferably have the following meanings, individually or in combination:
  • R 1 is hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkylsulfonyl, C 1 -C 6 - Haloalkyl sulfonyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl,
  • C 3 -C 6 cycloalkyl phenyl, heterocyclyl, phenylsulfonyl, heterocyclylsulfonyl, phenylcarbonyl, heterocyclylcarbonyl, phenyl-C 1 -C 6 -alkyl, heterocyclyl-C 1 -C 6 -alkyl,
  • halogen C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylcarbonyl, nitro, hydroxy or cyano, preferably selected from halogen, C 1 -C 4 alkyl, nitro or cyano; phenyl and heterocyclyl are particularly preferred
  • R 2 halogen, especially fluorine or chlorine, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, especially methylsulfonyl;
  • R 3 is hydrogen, fluorine or chlorine, especially hydrogen
  • R 17 is hydrogen or C 1 -C 4 alkyl, in particular hydrogen or methyl.
  • Hex in formula I preferably represents a radical of the formula Ha.
  • heterocyclyl is preferably unsaturated, aromatic heterocyclyl, which is especially C-bonded.
  • R 1 is C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 3 -C 6 cycloalkyl, C 1 -C 4 alkylsulfonyl, phenyl, phenyl-C 1 -C 4 alkyl or phenylsulfonyl, where the phenyl ring of the three latter groups can be substituted in the manner described above and in particular in the 4-position can have halogen or C 1 -C 4 -alkyl.
  • R 1 examples of particularly preferred radicals R 1 are: methyl, ethyl, n-propyl, isopropyl, tert. -Butyl, methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, cyclopropyl, phenyl, 4-methylphenyl, 4-chlorophenyl, benzyl, 1- and 2-phenylethyl, methyl, ethylsulfonyl, phenylsulfonyl, 4-methylphenylsulfonyl and 4-chlorophenylsulfonyl.
  • R 1 and R 17 preferably have the following meanings: R 1 C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 3 -C 6 cycloalkyl, C 1 -C 4 alkylsulfonyl, phenyl, phenyl-C 1 -C 4 alkyl or phenylsulfonyl, where the phenyl ring of the last three groups mentioned can be substituted in the 4-position with halogen or C 1 -C 4 alkyl,
  • R 17 is hydrogen or C 1 -C 4 alkyl.
  • NR 1 R 17 particularly preferably represents C 1 -C 4 -alkylamino, di-C 1 -C 4 -alkylamino, phenyl-C 1 -C 4 -alkylamino.
  • R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 preferably have the following meanings:
  • R 4 hydroxy, mercapto, halogen, OR 11 , SR 11 , S0 2 R 12 , OS0 2 R 12 , NR 15 R 16 and N-linked nitrogen heterocyclyl which can be partially or completely halogenated and / or one, two or three of the following radicals: nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy; wherein R 11 , R 12 , R 15 and R 16 have the meanings given above and in particular the meanings given below; R 4 stands in particular for hydroxy, C 1 -C 4 alkylcarbonyloxy, C 1 -C 4 alkylamino, di-C 1 -C 4 alkylamino, C 1 -C 4 alkylthio, N- (C 1 -C 4- alkyloxy) -N- (C 1 -C 4 -alkyl) amino, C
  • Phenyl group can preferably be substituted in the 4-position with halogen or C 1 -C 4 alkyl;
  • R 4 are hydroxyl, acetyl, methylsulfonyl, methylsulfonyloxy, phenylthio, 4-methylphenylthio, 4-chlorophenylthio, phenylsulfonyl, 4-methylphenylsulfonyl, 4-chlorophenylsulfonyl, phenylsulfonyloxy, 4-methylphenylsulfonyloxy, 4-methylphenylamino, 4-chlorophenylamino, 4-chlorophenylamino, 4-methylphenylamino, 4-chlorophenylamino -Methoxy-N-methylamino, N-ethoxy-N-methylamino, N-methoxy-N-ethylamino, N-ethoxy-N-ethylamino, N-
  • R 5 , R 9 are hydrogen or C 1 -C 4 alkyl, such as methyl, ethyl or propyl; especially hydrogen or methyl;
  • R 6 , R 8 , R 10 are hydrogen or C 1 -C 4 alkyl, such as methyl, ethyl or propyl; especially hydrogen or methyl;
  • R 7 is hydrogen, hydroxy, C 1 -C 6 -alkyl, di- (C 1 -C 6 -alkoxy) -methyl, (C 1 -C 6 -alkoxy) - (C 1 -C 6 -alkylthio) - methyl,
  • C 1 -C 6 alkylthio Di (C 1 -C 6 alkylthio) methyl, C 1 -C 6 alkylthio, C 1 -C 6 haloalkylthio, C 1 -C 6 alkylsulfinyl, C 1 -C 6 haloalkylsulfinyl, C 1 -C 6 Alkylsulfonyl or C 1 -C 6 haloalkylsulfonyl;
  • R 6 and R 8 or R 8 and R 10 together form a ⁇ bond or a C 3 -C 5 alkyl chain which can carry one to three radicals from the following group: halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 alkoxycarbonyl; or
  • R 6 and R 10 or R 5 and R 9 together form a C 1 -C 4 alkyl chain which can carry one to three radicals from the following group: halogen, cyano, C 1 -C 4 alkyl, C 1 - C 4 haloalkyl or C 1 -C 4 alkoxycarbonyl; or
  • R 7 and R 8 together form a -O- (CH 2 ) p -O-, -O- (CH 2 ) p -S- or -S- (CH 2 ) p -S chain, which is represented by one to three Radicals from the following group can be substituted: halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 alkoxycarbonyl; or
  • R 7 and R 8 together with the carbon to which they are attached form a carbonyl group.
  • the variable p is preferably 2 or 3 and the variable q is preferably 2, 3 or 4.
  • heterocyclyl preferably represents saturated, N-bonded heterocyclyl, in particular monocyclic, 5- or 6-ring heterocyclyl, which optionally contains a further hetero atom, for example oxygen or sulfur, imino or C 1 -C 6 -alkylimino in the ring having.
  • Preferred meanings for R 11 to R 16 are:
  • R 11 is C 1 -C 6 alkyl, C 3 -C 5 alkenyl, C 3 -C 6 haloalkenyl,
  • C 1 -C 6 -alkyl in particular C 1 -C 6 -alkyl, C 3 -C 6 -alkenyl, C 3 -C 6 -alkynyl, C 1 -C 6 -alkylcarbonyl, C 1 -C 6 -alkoxycarbonyl, C 1 -C 6 -alkylaminocarbonyl or N, -Di (C 1 -C 6 alkyl) aminocarbonyl, where the alkyl or alkoxy radicals mentioned can be partially or completely halogenated and / or can carry one to three of the following groups: cyano, C 1 -C 4 alkoxy , C 1 -C 4 alkylthio or C 1 -C 4 alkoxycarbonyl;
  • R 12 is C 1 -C 6 alkyl, C 3 -C 6 alkenyl or C 3 -C 6 cycloalkyl, where the three radicals mentioned can be partially or completely halogenated and / or can carry one to three of the following groups: cyano , C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylcarbonyl or C 1 -C 4 alkoxycarbonyl;
  • R 13 , R 14 hydroxy, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, phenyl, phenyl-C 1 -C 4 alkyl or phenoxy, where the latter three substituents can be partially or completely halogenated and / or may carry one to three of the following radicals: nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 halo-alkyl, C 1 -C 4 alkoxy, C 1 -C 4 -haloalkoxy or C 1 -C 4 alkoxycarbonyl;
  • R 15 is C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkoxy, C 3 -C 6 alkenyloxy or
  • Di- (C 1 -C 6 alkyl) amino where the alkyl, cycloalkyl or alkoxy radicals mentioned can be partially or completely halogenated and / or can carry one to three of the following radicals: cyano, C 1 -C 4 Alkoxycarbonyl, C 1 -C 4 alkylaminocarbonyl, di (C 1 -C 4 alkyl) aminocarbonyl or C 3 -C 6 cycloalkyl;
  • R 16 is C 1 -C 6 alkyl or C 3 -C 6 alkenyl
  • R 5 , R 9 are hydrogen or C 1 -C 4 alkyl
  • R 6 , R 8 , R 10 are hydrogen or C 1 -C 4 alkyl
  • R 7 is hydrogen, hydroxy, C 1 -C 6 alkyl, in particular C 1 -C 4 alkyl, di- (C 1 -C 6 alkoxy) methyl,
  • R 5 and R 9 or R 6 and R 10 together form a C 1 -C 4 alkyl chain which can carry one to three radicals from the following group: halogen, C 1 -C 4 alkyl or C 1 -C 4 -Haloalkyl; in particular R 6 and R 10 together form a methylene or an ethylene bridge which can carry one or two radicals from the following group: halogen, C 1 -C 2 alkyl or C 1 -C 2 haloalkyl; or
  • R 7 and R 8 together with the carbon to which they are attached form a carbonyl group.
  • R 5 , R 6 , R 7 , R 8 , R 9 and R 10 independently of one another represent hydrogen or C 1 -C 4 alkyl
  • R 7 can also represent hydroxy, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, haloalkoxy or haloalkylthio, or
  • R 7 and R 8 together with the carbon atom to which they are attached are also a carbonyl group, a 1, 3-dioxolane, 1, 3-dithiolane, 1, 3-oxothiolane, 1,3-oxothiane,
  • R 11 and R 12 can mean 1,3-dithiolane or a 1,3-dithiane ring, the 2-position of the six rings mentioned being identical to the carbon atom to which R 11 and R 12 are bonded, and / or R 5 and R 9 or R 6 and R 10 can also mean a C 1 -C 4 alkylene chain, or
  • R 6 and R 8 or R 8 and R 9 together can form a ⁇ bond.
  • R 4 and X have the meaning given in one row of Table A (compounds III to 1.1.135).
  • R 4 and X have the meaning given in one row of Table A (compounds 1.2.1 to 1.2.135).
  • R 4 and X have the meaning given in one row of Table A (compounds 1.3.1 to 1.3.135).
  • R 4 and X have the meaning given in one row of Table A (compounds 1.4.1 to 1.4.135).
  • R 4 and X have the meaning given in one row of Table A (compounds 1.5.1 to 1.5.135).
  • R 4 and X have the meaning given in one row of Table A (compounds 1.6.1 to 1.6.135).
  • R 4 and X have the meaning given in one row of Table A (compounds 1.7.1 to 1.7.135).
  • R 4 and X have the meaning given in one row of Table A (compounds 1.1.8 to 1.8.135).
  • R 4 and X have the meaning given in one row of Table A (compounds 1.9.1 to 1.9.135).
  • R 4 and X have the meaning given in one row of Table A (compounds 1.10.1 to 1.10.135).
  • R 4 and X have the meaning given in one row of Table A (compounds 1.11.1 to 1.11.135).
  • R 4 and X have the meaning given in one row of Table A (compounds 1.12.1 to 1.12.135).
  • R 4 and X have the meaning given in one row of Table A (compounds 1.13.1 to 1.13.135).
  • R 4 and X have the meaning given in one row of Table A (compounds 1.14.1 to 1.14.135).
  • R 4 and X have the meaning given in one row of Table A (compounds 1.15.1 to 1.15.135).
  • R 4 and X have the meaning given in one row of Table A (compounds 1.16.1 to 1.15.135).
  • R 4 and X have the meaning given in one row of Table A (compounds 1.17.1 to 1.17.135).
  • R 4 and X have the meaning given in one row of Table A (compounds 1.18.1 to 1.18.135).
  • R 4 and X have the meaning given in one row of Table A (compounds 1.19.1 to 1.19.135).
  • R 4 and X have the meaning given in one row of Table A (compounds 1.20.1 to 1.20.135).
  • R 4 and X have the meaning given in one row of Table A (compounds 1.21.1 to 1.21.135).
  • L 1 stands for a nucleophilically displaceable leaving group, such as halogen, for example bromine or chlorine, N-linked aromatic heterocyclic, for example imidazolyl or pyridyl, carboxylate, for example acetate or trifluoroacetate etc.
  • halogen for example bromine or chlorine
  • N-linked aromatic heterocyclic for example imidazolyl or pyridyl
  • carboxylate for example acetate or trifluoroacetate etc.
  • the activated carboxylic acid IVb can be used directly, as in the case of the benzoyl halides, or can be generated in situ from the carboxylic acid IVa, for example with carbodiimides such as ethyl- (3 '-dimethyl-laminopropyl) carbodiimide, dicyclohexylcarbodiimide, triphenylphosphine / azodicarboxylic acid ester, 2 —Pyridine disulfide / triphenylphosphine, carbonyldiimidazole etc.
  • carbodiimides such as ethyl- (3 '-dimethyl-laminopropyl) carbodiimide, 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 slight excess of the auxiliary base e.g. Under certain circumstances, 1.2 to 1.5 molar equivalents, based on IVa or IVb, can be advantageous.
  • Tertiary alkyl amines, pyridine or alkali metal carbonates are suitable as auxiliary bases.
  • a solvent e.g. chlorinated hydrocarbons such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons such as toluene, xylene or chlorobenzene, ethers such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran or dioxane, polar aprotic solvents such as acetonitrile, dimethylformamide or dimethyl sulfoxide or Esters such as ethyl acetate or mixtures thereof can be used.
  • chlorinated hydrocarbons such as methylene chloride or 1,2-dichloroethane
  • aromatic hydrocarbons such as toluene, xylene or chlorobenzene
  • ethers such as diethyl ether, methyl tert-butyl ether, tetrahydr
  • halides are used as the activated carboxylic acid component, it may be expedient to cool the reaction mixture to about 0 to 10 ° C. when this reaction partner is added. The mixture is then stirred at 20 to 100 ° C, preferably at 25 to 50 ° C, until the reaction is complete. The processing takes place in the usual way, e.g. the reaction mixture is poured onto water and the product of value is 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 ester can be used for rearrangement without further purification.
  • the rearrangement of the esters to the compounds of the formula I is advantageously carried out at from 20 to 100 ° C. in a solvent and in the presence of a base and, if appropriate, using a cyano compound as a catalyst.
  • acetonitrile, methylene chloride, 1,2-dichloroethane, dioxane, ethyl acetate, toluene or mixtures thereof can be used as solvents.
  • Preferred solvents are acetonitrile and dioxane.
  • Suitable bases are tertiary amines such as triethylamine, aromatic amines such as pyridine or alkali carbonates such as sodium carbonate or potassium carbonate, which are preferably used in an equimolar amount or up to a fourfold excess, based on the ester.
  • Triethylamine or alkali carbonate are preferably used, preferably in a double equimolar ratio with respect to the ester.
  • Inorganic cyanides such as sodium cyanide or potassium cyanide and organic cyano compounds such as acetone cyanohydrin or trimethylsilyl cyanide are suitable as cyano compounds. They are used in an amount of 1 to 50 mol%, based on the ester. Preferably acetone cyanohydrin or trimethylsilyl cyanide, e.g. in an amount of 5 to 15, preferably about 10 mol%, based on the ester.
  • the reaction mixture is e.g. acidified with dilute mineral acid such as 5% hydrochloric acid or sulfuric acid, with an organic solvent, e.g. Extracted methylene chloride or ethyl acetate.
  • the organic extract can be mixed with 5-10% alkali carbonate solution, e.g. Sodium carbonate or potassium carbonate solution can be extracted.
  • the aqueous phase is acidified and the precipitate formed is suction filtered and / or extracted with methylene chloride or ethyl acetate, dried and concentrated.
  • acylation of the carboxylic acid IVa or IVb and the subsequent rearrangement to the compound I can also be carried out as a "one-pot reaction", i.e. can be carried out without isolation of the ester.
  • Suitable halogenating agents are, for example, phosgene, diphosgene, triphosgene, thionyl chloride, oxalyl chloride, phosphorus oxychloride, phosphorus pentachloride, mesyl chloride, chloromethylene-N, N-dimethylammonium chloride, oxalyl bromide, phosphorus oxybromide, etc.
  • L 2 stands for a nucleophilically displaceable leaving group, such as halogen, for example chlorine or bromine, hetaryl, for example imidazolyl, carboxylate, for example acetate, or sulfonate, for example mesylate or triflate etc.
  • halogen for example chlorine or bromine
  • hetaryl for example imidazolyl
  • carboxylate for example acetate
  • sulfonate for example mesylate or triflate etc.
  • the compounds of the formula V ⁇ , Vß, V ⁇ or V ⁇ can be used directly, e.g. in the case of carboxylic acid halides or generated in situ, e.g. activated carboxylic acids (with carboxylic acid and dicyclohexylcarbodiimide etc.).
  • Suitable oxidizing agents are m-chloroperbenzoic acid, peroxyacetic acid, trifluoroperoxyacetic acid, hydrogen peroxide, if appropriate in the presence of a catalyst such as tungstate.
  • 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.
  • reactants and the base are expediently used in equimolar amounts.
  • Suitable bases are tertiary alkylamines, such as triethylamine, aromatic amines, such as pyridine, alkali metal carbonates, for example sodium carbonate or potassium carbonate, and metal hydrogen carbonates, such as Sodium bicarbonate and potassium bicarbonate, alkali metal alcoholates such as sodium methoxide, sodium ethanolate, potassium tert-butoxide or alkali metal hydrides, for example sodium hydride. Triethylamine or pyridine are preferably used.
  • solvents examples include chlorinated hydrocarbons such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons e.g. Toluene, xylene or chlorobenzene, ethers such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran or dioxane, polar aprotic solvents such as acetonitrile, dimethylformamide or dimethyl sulfoxide or esters such as ethyl acetate, or mixtures thereof.
  • chlorinated hydrocarbons such as methylene chloride or 1,2-dichloroethane
  • aromatic hydrocarbons e.g. Toluene, xylene or chlorobenzene
  • ethers such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran or dioxane
  • polar aprotic solvents such as acetonitrile, dimethyl
  • reaction temperature is in the range from 0 ° C. to the boiling point of the reaction mixture.
  • the product can be worked up in a manner known per se.
  • compounds Ia, Ib or mixtures thereof can be formed in processes B to D.
  • the latter can be separated using classic separation methods, e.g. Crystallization, chromatography, etc., are separated.
  • cyclohexanediones of the formula III used as starting materials are known or can be prepared by processes known per se (e.g. EP-A 71 707, EP-A 142 741, EP-A 243 313, US 4,249,937, WO 92/13821).
  • alkylating agents V ⁇ , sulfonylating agents Vß, phosphonizing agents V ⁇ and V ⁇ , and the compounds Vl ⁇ , Vlß, Vl ⁇ , Vl ⁇ and Vl ⁇ are also known or can be prepared by known processes.
  • the carboxylic acids of the general formula IVa or their activated derivatives IVb can be prepared in analogy to known processes.
  • the carboxylic acids IVa and their activated derivatives IVb are new and also the subject of the present invention.
  • Alkali metal hydroxides such as sodium hydroxide or potassium hydroxide, alkali metal carbonates such as sodium carbonate or potassium carbonate or acetates such as sodium acetate are suitable as the base.
  • Suitable bases are e.g. Alkali metal carbonates such as sodium carbonate or potassium carbonate, alkali metal hydrogen carbonates such as sodium hydrogen carbonate or tertiary amines such as e.g. Triethylamine or pyridine.
  • Suitable oxidizing agents are, for example, m-chloroperbenzoic acid, peroxyacetic acid, trifluoroperoxyacetic acid, hydrogen peroxide, optionally in the presence of a catalyst such as tungsten, halogens or oxygen, preferably in the presence of photosensitizers.
  • a catalyst such as tungsten, halogens or oxygen, preferably in the presence of photosensitizers.
  • Suitable auxiliary bases are, for example, alkali metal carbonates such as sodium carbonate or potassium carbonate, tertiary amines such as e.g. Triethylamine or pyridine, alkali metal hydrides such as e.g. Sodium hydride or potassium hydride or sterically demanding alcohols such as e.g. Potassium tert-butoxide.
  • alkali metal carbonates such as sodium carbonate or potassium carbonate
  • tertiary amines such as e.g. Triethylamine or pyridine
  • alkali metal hydrides such as e.g. Sodium hydride or potassium hydride
  • sterically demanding alcohols such as e.g. Potassium tert-butoxide.
  • Suitable halogenating agents are chlorine, bromine, N-chloramine, N-chlorosuccinimide and N-bromosuccinimide.
  • the reaction is preferably carried out in the presence of a radical initiator.
  • a radical initiator benzoyl peroxide or azobisisobutyronitrile, among others, are suitable.
  • suitable radiation sources such as UV-Hg low-pressure or Hg high-pressure lamps and / or with heating without carrying out an external radical starter.
  • Table 1 below also lists further cyclohexenone derivatives of the formula Ia, which were prepared in an analogous manner starting from precursor 1, 2, 3 and 4.
  • the compounds of formula 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 which contain compounds of the formula I control vegetation very well on non-cultivated areas, especially 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 above all at low application rates.
  • the compounds of the formula I or herbicidal compositions comprising them can also be used in a further number of crop plants for eliminating undesired plants.
  • the following crops are considered, for example:
  • Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarle, Seeale Solanum tuberosum, Sorghum bicolor (see vulgar), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.
  • the compounds Ia or Ib 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 substances are less compatible for certain crop plants, application techniques can be used in which the herbicidal compositions are sprayed with the aid of the spray
  • 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 soils such as silicas, 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, Urea and vegetable products such as flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
  • the concentrations of the active ingredients Ia or Ib in the ready-to-use preparations can be varied within 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 substance.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).
  • the compounds Ia or Ib according to the invention can be formulated, for example, as follows:
  • I 20 parts by weight of compound no. 4 are dissolved in a mixture consisting of 80 parts by weight of alkylated benzene, 10 parts by weight of the adduct of 8 to 10 mol of ethylene oxide and 1 mol of oleic acid-N-monoethanolamide, 5 parts by weight of calcium salt of dodecylbenzenesulfonic acid and 5 parts by weight of the adduct of 40 moles of ethylene oxide to 1 mole of castor oil.
  • aqueous dispersion is obtained which contains 0.02% by weight of the active ingredient.
  • V 3 parts by weight of active ingredient No. 4 are mixed with 97 parts by weight of finely divided kaolin. In this way, a dust is obtained which contains 3% by weight of the active ingredient.
  • the cyclohexenone derivatives as s Ia or Ib 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, benzothiadiazinones come as mixing partners , 2-aroyl-l, 3-cyclohexanediones, hetaryl aryl ketones, benzylisoxazolidinones, meta-CF 3 phenyl derivatives, carbamates, quinolinecarboxylic acid and their derivatives, chloroacetanilides, cyclohexane-1, 3-dione derivatives, diazines, dichloropropionic acid and their derivatives,
  • the compounds Ia or Ib may also be useful to apply the compounds Ia or Ib, alone or in combination with other herbicides, mixed with other crop protection agents, for example with agents for controlling pests or phytopathogenic fungi or bacteria.
  • the miscibility with mineral salt solutions which are used to remedy nutritional and trace element deficiencies.
  • Non-phytotoxic oils and oil concentrates can also be added.
  • the active compound application rates are 0.001 to 3, preferably 0.01 to 1.0 kg / ha of active substance (see p.).
  • the herbicidal activity of the cyclohexenone derivatives as s of the formula ia or Ib was demonstrated by greenhouse tests: Plastic pots with loamy sand with about 3.0% humus as substrate served as culture vessels. The seeds of the test plants were sown separately according to species.
  • 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 causes the test plants to germinate evenly, unless this was affected by the active ingredients.
  • test plants were each 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 application rate for post-emergence treatment was 0.5, 0.25 and 0.125 kg / ha of active substance.
  • the plants were kept in a species-specific manner at temperatures of 10 to 25 25 ° C and 20 to 35 ° C.
  • the trial period lasted 2 to 4 weeks. During this time, the plants were cared for and their response to each treatment was evaluated.
  • the compound from example no. 14 showed a very good herbicidal activity against POLPE, CHEAL and PHBPU and a good herbicidal activity against ABUTH at post-emergence application and application rates of 0.5 kg / ha aS. At application rates of 0.25 kg / ha aS, the compound from Example 14 showed good to very good herbicidal activity against ABUTH, POLPE, CHEAL and PHPBU. A high selectivity for wheat (TRZAS, no damage) was observed at both application rates.
  • the compound from Example 23 showed a very good herbicidal activity against ABUTH, CHEAL and POLPE and a good activity against ECHCG with simultaneous high selectivity towards wheat (TRZAS.) With post-emergence application and application rates of 0.25 or 0.5 kg / ha aS ).

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
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Abstract

Dérivés cyclohexénone d'acides benzoïques bicycliques de formule générale (I) dans laquelle X, R2 et R3 possèdent la signification figurant dans la revendication 1. La présente invention concerne également des herbicides qui contiennent des dérivés de cyclohexénone de formule (I), des procédés de préparation de ces herbicides et des procédés de lutte contre les plantes nuisibles à l'aide desdits dérivés.
PCT/EP2000/005790 1999-06-25 2000-06-23 Derives cyclohexenone d'acide benzoique en tant qu'herbicides WO2001000607A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU59771/00A AU5977100A (en) 1999-06-25 2000-06-23 Cyclohexenone derivatives of bicyclic benzoic acids as herbicides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19929259.0 1999-06-25
DE1999129259 DE19929259A1 (de) 1999-06-25 1999-06-25 Cyclohexanon-Derivate von bicyclischen Benzoesäuren

Publications (1)

Publication Number Publication Date
WO2001000607A1 true WO2001000607A1 (fr) 2001-01-04

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PCT/EP2000/005790 WO2001000607A1 (fr) 1999-06-25 2000-06-23 Derives cyclohexenone d'acide benzoique en tant qu'herbicides

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Country Link
AU (1) AU5977100A (fr)
DE (1) DE19929259A1 (fr)
WO (1) WO2001000607A1 (fr)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4521241A (en) * 1983-09-19 1985-06-04 E. I. Du Pont De Nemours And Company Herbicidal benzenesulfonamides
EP0283261A2 (fr) * 1987-03-19 1988-09-21 Zeneca Limited Diones cycliques substituées, herbicides
US5480858A (en) * 1992-08-18 1996-01-02 Idemitsu Kosan Co., Ltd. Cyclohexanedione derivatives
US5518994A (en) * 1992-04-15 1996-05-21 Nissan Chemical Industries, Ltd. 2-arylaminopyrimidinone derivative, and herbicide and plant growth regulator
WO1997008164A1 (fr) * 1995-08-25 1997-03-06 E.I. Du Pont De Nemours And Company Herbicides bicycliques
WO1997009324A1 (fr) * 1995-09-01 1997-03-13 Basf Aktiengesellschaft Derives benzoyle 2-cyclohexane-1,3-dione

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4521241A (en) * 1983-09-19 1985-06-04 E. I. Du Pont De Nemours And Company Herbicidal benzenesulfonamides
EP0283261A2 (fr) * 1987-03-19 1988-09-21 Zeneca Limited Diones cycliques substituées, herbicides
US5518994A (en) * 1992-04-15 1996-05-21 Nissan Chemical Industries, Ltd. 2-arylaminopyrimidinone derivative, and herbicide and plant growth regulator
US5480858A (en) * 1992-08-18 1996-01-02 Idemitsu Kosan Co., Ltd. Cyclohexanedione derivatives
WO1997008164A1 (fr) * 1995-08-25 1997-03-06 E.I. Du Pont De Nemours And Company Herbicides bicycliques
WO1997009324A1 (fr) * 1995-09-01 1997-03-13 Basf Aktiengesellschaft Derives benzoyle 2-cyclohexane-1,3-dione

Also Published As

Publication number Publication date
DE19929259A1 (de) 2000-12-28
AU5977100A (en) 2001-01-31

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