WO2001000607A1 - Cyclohexenone derivatives of bicyclic benzoic acids as herbicides - Google Patents

Cyclohexenone derivatives of bicyclic benzoic acids as herbicides Download PDF

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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)
French (fr)
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/en

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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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Abstract

The invention relates to cyclohexenone derivatives of bicyclic benzoic acids of the general formula (I), wherein X, R?2 and R3¿ are defined as indicated in claim 1. The invention also relates to herbicidal agents that contain the cyclohexenone derivatives of formula (I), to a method of producing said agents and to a method of combating undesired plant growth using the cyclohexenone derivatives of formula (I).

Description

CYCLOHEXENONDERIVATE VON BICYCLISCHEN BENZOESÄUREN ALS HERBIZIDECYCLOHEXENONE DERIVATIVES OF BICYCLIC BENZOIC ACIDS AS HERBICIDES
5 Beschreibung5 Description
Die vorliegende Erfindung betrifft Cyclohexenon-Derivate von bi- cyclischen Benzoesäuren, die in 2,3-Position einen anellierten, gesättigten Heterocyclus aufweisen, Verfahren zur Herstellung 0 derartiger Cyclohexenon-Derivate, Mittel, die derartige Verbindungen enthalten, sowie die Verwendung der Cyclohexenon-Derivate oder Mittel, die diese enthalten, zur Schadpflanzenbekämpfung.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.
Aus der WO 97/09324 sind Cyclohexan-1, 3-dione mit Herbizid-Wir- 5 kung bekannt, die in der 2-Position einen benzokondensiertenWO 97/09324 discloses cyclohexane-1,3-diones with herbicidal action which have a benzo-condensed position in the 2 position
Schwefel-Heterocyclus, z.B. einen Thiochroman- oder einen Benzo- dihydrothiophen-Rest aufweisen, der über eine Carbonylgruppe gebunden ist.Sulfur heterocycle, e.g. have a thiochroman or a benzodihydrothiophene radical which is bonded via a carbonyl group.
0 Aus der WO 97/08164 sind Herbizide bekannt, die einen Cyclohexe- nonrest aufweisen, der in der 2-Position mit einem bicyclischen Arylcarbonylrest substituiert ist. Als Beispiele für Arylcarbo- nylreste werden benzokondensierte Lactone wie Benzfuranon, Benzo- pyranon, Lactame wie Benzopyrrolidon und Benzopyrimidon, 5 2,3-Benzo-4, 5-dihydrothiophendioxid und 2,3-Benzo-4,5,6, 7-tetra- hydrothiepindioxid genannt.Herbicides are known from WO 97/08164 which have a cyclohexenone radical which is substituted in the 2-position by a bicyclic arylcarbonyl radical. Examples of 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.
Die herbiziden Eigenschaften der aus den genannten Druckschriften bekannten Verbindungen sowie deren Verträglichkeiten gegenüber 0 Kulturpflanzen vermögen jedoch nur bedingt die Anforderungen an Herbizide zu befriedigen.However, the herbicidal properties of the compounds known from the publications mentioned and their compatibility with crop plants are only able to meet the requirements for herbicides to a limited extent.
Der vorliegenden Erfindung liegt somit die Aufgabe zugrunde neue Verbindungen mit herbizider Wirkung bereitzustellen, die vorzugs- 5 weise eine höhere Wirksamkeit als die herbiziden Substanzen des Standes der Technik und/oder eine bessere Selektivität gegenüber Schadpflanzen aufweisen.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.
Es wurde nun überraschenderweise gefunden, dass diese Aufgabe 0 durch die nachstehend definierten Cyclohexenon-Derivate von bicyclischen Benzoesäuren, die in 2,3-Position einen anellierten, gesättigten Heterocyclus aufweisen, gelöst wird.It has now surprisingly been found that this problem is solved by the cyclohexenone derivatives of bicyclic benzoic acids defined below which have a fused, saturated heterocycle in the 2,3-position.
Demnach betrifft die vorliegende Erfindung Cyclohexenon-Derivate 5 von bicyclischen Benzoesäuren der allgemeinen Formel I,
Figure imgf000003_0001
Accordingly, the present invention relates to cyclohexenone derivatives 5 of bicyclic benzoic acids of the general formula I,
Figure imgf000003_0001
worinwherein
X für 0, S , SO , S02 , N-R1 oder N-NR1R17 steht,X represents 0, S, SO, S0 2 , NR 1 or N-NR 1 R 17 ,
R1 Wasserstoff , C1-C6-Alkyl , C1-C6-Halogenalkyl , C1-C6-Alkoxy, C1-C6-Halogenalkoxy, C1-C6-Alkylsulfonyl , C1-C6-Halogenalkyl- sulfonyl , C1-C6-Alkoxy-C1-C6-alkyl , C1-C6-Alkylcarbonyl , C1-C6-Halogenalkylcarbonyl , C1-C6-Alkylcarbonyl-C1-C6-alkyl , C1-C6-Alkylcarbonyl-C1-C6-alkylcarbonyl , C1-C6-Alkylcarbony- loxy-C1-C6-alkyl ,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,
C3-C6-Cycloalkyl , C3-C6-Cycloalkoxy, C3-C6-Cycloalkylcarbonyl , C3-C6-Cycloalkyl-C1-C6-alkyl , C3-C6-Cycloalkoxy-C1-C6-alkyl ,C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkoxy, C 3 -C 6 cycloalkylcarbonyl, C 3 -C 6 cycloalkyl-C 1 -C 6 alkyl, C 3 -C 6 cycloalkoxy-C 1 -C 6 alkyl,
C3-C6-Cycloalkylcarbonyl-C1-C6-alkyl , C3-C6-Cycloalkoxycarbo- nyl-C1-C6-alkyl , C3-C6-Cycloalkylcarbonyloxy-C1-C6-alkyl , C3-C6-Cycloalkylsulfonyl ,C 3 -C 6 cycloalkylcarbonyl-C 1 -C 6 alkyl, C 3 -C 6 cycloalkoxycarbonyl-C 1 -C 6 alkyl, C 3 -C 6 cycloalkylcarbonyloxy-C 1 -C 6 alkyl, C 3 -C 6 cycloalkylsulfonyl,
Phenyl , Phenylsulfonyl , Phenylcarbonyl , Phenyl-C1-C6-alkyl , Phenyl-C1-C6-alkylcarbonyl , Phenoxy-C1-C6 -alkyl , Phenylcarbo- nyl-C1-C6-alkyl , Phenoxycarbonyl-C1-C6-alkyl oder Phenylcarbo- nyloxy-C1-C6-alkyl bedeuten ,Phenyl, phenylsulfonyl, phenylcarbonyl, phenyl-C 1 -C 6 -alkyl, phenyl-C 1 -C 6 -alkylcarbonyl, phenoxy-C 1 -C 6 -alkyl, phenylcarbonyl-C 1 -C 6 -alkyl, phenoxycarbonyl- C 1 -C 6 alkyl or phenylcarbonyloxy-C 1 -C 6 alkyl,
Heterocyclyl , Heterocyclylsulfonyl , Heterocyclylcarbonyl , Heterocyclyl-C1-C6-alkyl , Heterocyclylcarbonyl-C1-C6-alkyl oder Heterocyclylcarbonyloxy-C1-C6-alkyl bedeuten,Are heterocyclyl, heterocyclylsulfonyl, heterocyclylcarbonyl, heterocyclyl-C 1 -C 6 -alkyl, heterocyclylcarbonyl-C 1 -C 6 -alkyl or heterocyclylcarbonyloxy-C 1 -C 6 -alkyl,
wobei die Phenyl-, Heterocyclyl- und Cycloalkylreste der vorgenannten Gruppen gegebenenfalls eine, zwei, drei oder vier Substituenten ausgewählt unter C1-C4-Alkyl, C1-C4-Halogenal- kyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy, C1-C4-Alkylcarbonyl, C1-C4-Halogenalkylcarbonyl, C1-C4-Alkylsulfonyl, C1-C4-Haloge- nalkylsulfonyl, Nitro, Hydroxy oder Cyano tragen und/oder teilweise oder vollständig halogeniert sein können;where the 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;
R2 für Halogen, C1-C6-Alkylthio, C1-C6-Halogenalkylthio, C1-C6-Alkylsulfinyl, C1-C6-Halogenalkylsulfinyl, C1-C6-Alkyl- sulfonyl oder C1-C6-Halogenalkylsulfonyl; R3 für Wasserstoff, Halogen, C1-C6-Alkyl oder C1-C6-Halogenalkyl, undR 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
Hex für substituiertes (3-Oxo-l-cyclohexen-2-yl)carbonyl der Formel Ha oder für substituiertesHex for substituted (3-oxo-l-cyclohexen-2-yl) carbonyl of the formula Ha or for substituted
( l,3-Dioxo-2-cyclohexyl)methyliden der Formel Ilb(1,3-Dioxo-2-cyclohexyl) methylidene of the formula IIb
Figure imgf000004_0001
Figure imgf000004_0001
stehen, wobei die Variablen R4 bis R10 folgende Bedeutung haben:stand, whereby the variables R 4 to R 10 have the following meaning:
R4 Hydroxy, Mercapto, Halogen, OR11, SR11, SOR12, S02R12,R 4 hydroxy, mercapto, halogen, OR 11 , SR 11 , SOR 12 , S0 2 R 12 ,
OSO2R12, P(O)R13R14, OP(0)R13R14, P(S)R13R14, OP(S)R13R14' NR15R16, ONR15R16 oder N-gebundenes Heterocyclyl, das partiell oder vollständig halogeniert sein kann und/oder einen, zwei oder drei der folgenden Reste tragen kann: Nitro, Cyano, Cι_C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy oder C1-C4-Halogenalkoxy;OSO 2 R 12 , P (O) R 13 R 14 , OP (0) R 13 R 14 , P (S) R 13 R 14 , OP (S) R 13 R 14 'NR 15 R 16 , ONR 15 R 16 or may carry N-linked heterocyclyl, which may be partially or fully halogenated and / or one, two or three of the following radicals: nitro, cyano, Cι_C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 - Alkoxy or C 1 -C 4 haloalkoxy;
R5, R9 unabhängig voneinander Wasserstoff, C1-C4-Alkyl oder C1-C4-Alkoxycarbonyl;R 5 , R 9 independently of one another are hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxycarbonyl;
R6, R8, R10 unabhängig voneinander Wasserstoff oder C1-C4-Alkyl;R 6 , R 8 , R 10 independently of one another are hydrogen or C 1 -C 4 alkyl;
R7 Wasserstoff, Halogen, Hydroxy, C1-C6-Alkyl, C1-C6-Halogenalkyl, Di-(C1-C6-alkoxy)-methyl, ( C1-C6-Alkoxy) -( C1-C6-alkylthio) -methyl, Di-(C1-C6-alkylthio)methyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy, C1-C6-Alkylthio, C1-C6-Halogenalkylthio, C1-C6-Alkylsulfinyl , C1-C6-Halogenalkylsulfinyl, C1-C6-Alkylsulfonyl, C1-C6-Halogenalkylsulfonyl, C1-C6-Alkoxycarbonyl, C1-C6-Halogenalkoxycarbonyl;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;
1, 3-Dioxolan-2-yl, 1, 3-Dioxan-2-yl, 1, 3-Oxathiolan-2-yl, 1 , 3-Oxathian-2-yl, l,3-Dithiolan-2-yl oder l,3-Dithian-2-yl, wobei die sechs letztgenannten Reste durch einen bis drei C1-C4-Alkylreste substituiert sein können; oder R6 und R8 oder R8 und R10 bilden gemeinsam eine π-Bindung oder eine Ci-Cs-Alkylkette, die einen zwei oder drei Reste aus folgender Gruppe tragen kann: Halogen, Cyano, C1-C -Alkyl, C1-C4-Halogenalkyl oder C1-C4-Alkoxycarbonyl; oder1,3-dioxolan-2-yl, 1,3-dioxan-2-yl, 1,3-oxathiolan-2-yl, 1,3-oxathian-2-yl, 1,3-dithiolan-2-yl or l, 3-dithian-2-yl, where the six latter radicals can be substituted by one to three C 1 -C 4 alkyl radicals; or R 6 and R 8 or R 8 and R 10 together form a π bond or a Ci-Cs-alkyl chain, which can carry one or two radicals from the following group: halogen, cyano, C 1 -C alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 alkoxycarbonyl; or
R6 und R10 bilden gemeinsam eine C1-C4-Alkylkette, die einen zwei oder drei Reste aus folgender Gruppe tragen kann: Halogen, Cyano, C1-C4-Alkyl, C1-C4-Halogenalkyl oder C1-C4-Alkoxycarbonyl; oderR 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
R7 und R8 bilden gemeinsam eine -O-(CH2)p-O-, -O-(CH2)p-S-,R 7 and R 8 together form an -O- (CH 2 ) p -O-, -O- (CH 2 ) p -S-,
-S-(CH2)P-S-, -O-(CH2)q- oder -S-(CH2)q-Kette, worin p für 2, 3, 4 oder 5 und q für 2, 3, 4, 5 oder 6 stehen, und die durch einen, zwei oder drei Reste aus folgender Gruppe substituiert sein kann: Halogen, Cyano, C1-C4-Alkyl, C1-C4-Halogenalkyl oder C1-C4-Alkoxycarbonyl; oder-S- (CH 2 ) P -S-, -O- (CH 2 ) q - or -S- (CH 2 ) q chain, in which p is 2, 3, 4 or 5 and q is 2, 3, 4, 5 or 6, and which can be substituted by one, two or 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
R7 und R8 bilden gemeinsam mit dem Kohlenstoff, an dem sie gebun- den sind, eine Carbonylgruppe ;R 7 and R 8 together with the carbon to which they are attached form a carbonyl group;
und worin die Variablen R11 bis R17 die folgenden Bedeutungen haben:and in which the variables R 11 to R 17 have the following meanings:
R11 C1-C6-Alkyl, C3-C6-Alkenyl, C3-C6-Halogenalkenyl,R 11 is C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl,
C3-C6-Alkinyl, C3-C6-Halogenalkinyl, C3-C6-Cycloalkyl, C1-C6-Alkylcarbonyl, C2-C6-Alkenylcarbonyl, C2-C6-Alkinylcarbonyl, C3-C6-Cycloalkylcarbonyl, C1-C6-Alkoxycarbonyl , C3-C6-Alkenyloxycarbonyl , C3-C6-Alkinyloxycarbonyl, C1-C6-Alkylthiocarbonyl, C1-C6-Alkylaminocarbonyl, C3-C6-Alkenylaminocarbonyl ,C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkylcarbonyl, C 2 -C 6 alkenylcarbonyl, C 2 -C 6 alkynylcarbonyl, C 3 -C 6 cycloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 3 -C 6 alkenyloxycarbonyl, C 3 -C 6 alkynyloxycarbonyl, C 1 -C 6 alkylthiocarbonyl, C 1 -C 6 alkylaminocarbonyl, C 3 -C 6- alkenylaminocarbonyl,
C3-C6-Alkinylaminocarbonyl , ,N-Di( C1-C6-alkyl )aminocarbonyl,C 3 -C 6 alkynylaminocarbonyl,, N-di (C 1 -C 6 alkyl) aminocarbonyl,
N-(C3-C6-Alkenyl) -N-( C1-C6-alkyl)-aminocarbonyl, N- (C3-C6-Alkinyl ) -N- ( C1-C6-al yl) -aminocarbonyl, N-( C1-C6-Alkoxy) -N- ( C1-C6-alkyl) -aminocarbonyl , N- (C3-C6-Alkenyl ) -N- ( C1-C6-alkoxy) -aminocarbonyl, N-(C3-C6-Alkinyl) -N-( C1-C6-alkoxy) -aminocarbonyl, Di-(C1-C6-alkyl)-aminothiocarbonyl, C1-C6-Alkoxyimino-C1-C6-alkyl, wobei die genannten Alkyl-, Cycloalkyl- oder Alkoxyreste partiell oder vollständig halogeniert sein können und/oder eine, zwei oder drei der folgenden Gruppen tragen können: Cyano, C1-C4-Alkoxy, C1-C4-Alkylthio, Di-(C1-C4-alkyl)amino, C1-C4-Alkylcarbonyl, C1-C4-Alkoxycarbonyl,N- (C 3 -C 6 -alkenyl) -N- (C 1 -C 6 -alkyl) -aminocarbonyl, N- (C 3 -C 6 -alkynyl) -N- (C 1 -C 6 -al yl) -aminocarbonyl, N- (C 1 -C 6 -alkoxy) -N- (C 1 -C 6 -alkyl) -aminocarbonyl, N- (C 3 -C 6 -alkenyl) -N- (C 1 -C 6 - alkoxy) -aminocarbonyl, N- (C 3 -C 6 -alkynyl) -N- (C 1 -C 6 -alkoxy) -aminocarbonyl, di- (C 1 -C 6 -alkyl) -aminothiocarbonyl, C 1 -C 6 -Alkoxyimino-C 1 -C 6 -alkyl, where the alkyl, cycloalkyl or alkoxy 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 alkylthio, di- (C 1 -C 4 alkyl) amino, C 1 -C 4 alkylcarbonyl, C 1 -C 4 alkoxycarbonyl,
C1-C4-Alkoxy-C1-C-alkoxycarbonyl, Hydroxycarbonyl, C1-C4-Alkylaminocarbo ( C1-C4-Alkyl ) aminocarbonyl , Aminocarbonyl , C!-C -Alkylcarbonyloxy oder C3-C6-Cycloalkyl ;C 1 -C 4 alkoxy-C 1 -C alkoxycarbonyl, hydroxycarbonyl, C 1 -C 4 alkylaminocarbo (C 1 -C 4 alkyl) aminocarbonyl, Aminocarbonyl, C ! -C -alkylcarbonyloxy or C 3 -C 6 cycloalkyl;
Phenyl , Phenyl-C1-C6-alkyl , Phenylcarbonyl-C1-C6-alkyl , Phenylcarbonyl , Phenoxycarbonyl , Phenoxythiocarbonyl ,Phenyl, phenyl-C 1 -C 6 -alkyl, phenylcarbonyl-C 1 -C 6 -alkyl, phenylcarbonyl, phenoxycarbonyl, phenoxythiocarbonyl,
Phenylaminocarbonyl ,Phenylaminocarbonyl,
N- ( C1-C6-Alkyl ) -N-phenylaminocarbonyl , Phenyl-C2-C6-alkenylcarbonyl , Heterocyclyl , Heterocyclyl-C1-C6-alkyl , Heterocyclylcarbonyl-C1-C6-alkyl , Heterocyclylcarbonyl,N- (C 1 -C 6 -alkyl) -N-phenylaminocarbonyl, phenyl-C 2 -C 6 -alkenylcarbonyl, heterocyclyl, heterocyclyl-C 1 -C 6 -alkyl, heterocyclylcarbonyl-C 1 -C 6 -alkyl, heterocyclylcarbonyl,
Heterocyclyloxycarbonyl , Heterocyclyloxythiocarbonyl , Heterocyclylaminocarbonyl ,Heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl, heterocyclylaminocarbonyl,
N- ( C1-C6-Alkyl ) -N-heterocyclylaminocarbonyl oder Hetero- cyclyl-C -C6-alkenylcarbonyl , wobei der Phenyl- oder der Heterocyclyl-Rest der 18 letztgenannten Substituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann : Nitro , Cyano , C1-C4-Alkyl , C1-C4-Halogenalkyl, C1-C4-Alkoxy oder C1-C4-Halogenalkoxy;N- (C 1 -C 6 -alkyl) -N-heterocyclylaminocarbonyl or heterocyclyl-C -C 6 -alkenylcarbonyl, where the phenyl or heterocyclyl radical of the latter 18 substituents can be partially or completely halogenated and / or one can carry up to 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;
R12 C1-C6-Alkyl, C3-C6-Alkenyl, C3-C6-Alkinyl oderR 12 is C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl or
C3-C6-Cycloalkyl, wobei die vier genannten Reste partiell oder vollständig halogeniert sein können und/oder eine, zwei oder drei der folgenden Gruppen tragen können: Cyano, C1-C4-Alkoxy, C1-C4-Halogenalkoxy, C1-C4-Alkylthio, C1-C4-Halogenalkylthio, C1-C4-Alkylcarbonyl, C1-C4-Alkoxycarbonyl oder C1-C4-Halogenalkoxycarbonyl,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,
Phenyl, Phenyl-C1-C4-alkyl, Heterocyclyl oder Heterocy- clyl-C1-C4-alkyl, wobei der Phenyl- oder der Heterocy- clylrest der vier letztgenannten Substituenten partiell oder vollständig halogeniert sein kann und/oder einen, zwei oder drei der folgenden Reste tragen kann: Nitro, Cyano, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy , C1-C4-Halogenalkoxy oder C1-C4-Alkoxycarbonyl;Phenyl, phenyl-C 1 -C 4 -alkyl, heterocyclyl or heterocyclic-C 1 -C 4 -alkyl, where the phenyl or heterocyclic radical of the four last-mentioned substituents can be partially or completely halogenated and / or one, can carry 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;
R13, R14 unabhängig voneinander Wasserstoff, Hydroxy, C1-C6-Alkyl, C1-C6-Alkoxy, C1-C6-Alkylthio, Phenyl, Phenyl-C1-C4-alkyl oder Phenoxy, wobei die drei letztgenannten Substituenten partiell oder vollständig halogeniert sein können und/ oder einen, zwei oder drei der folgenden Reste tragen können: Nitro, Cyano, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy oder C1-C4-Alkoxy- carbonyl; R15 Wasserstoff, C1-C6-Alkyl, C3-C6-Alkenyl,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,
C3-C6-Halogenalkenyl, C3-C6-Alkinyl, C3-C6-Halogenalkinyl, C3-C6-Cycloalkyl, C1-C6-Alkylcarbonyl, Hydroxy, C1-C6-Alkoxy, C3-C6-Alkenyloxy, C3-C6-Alkinyloxy, Amino, C1-C6-Alkyla ino, Di- (C1-C6-alkyl) amino oder C1-C6-Alkylcarbonylamino, wobei die genannten Alkyl-, Cycloalkyl- oder Alkoxyreste partiell oder vollständig halogeniert sein können und/oder einen, zwei oder drei der folgenden Reste tragen können: Cyano, C1-C4-Alkoxycarbonyl, C1-C4-Alkylaminocarbonyl,C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkylcarbonyl, hydroxy, C 1 -C 6 alkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy, amino, C 1 -C 6 alkylla ino, di (C 1 -C 6 alkyl) amino or C 1 -C 6 alkylcarbonylamino, where the mentioned alkyl, cycloalkyl or alkoxy radicals can be partially or completely halogenated and / or can carry one, two or three of the following radicals: cyano, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkylaminocarbonyl,
Di- (C1-C4-alkyl) aminocarbonyl oder C3-C6-Cycloalkyl,Di- (C 1 -C 4 alkyl) aminocarbonyl or C 3 -C 6 cycloalkyl,
Phenyl, Phenyl-C1-C4-alkyl, Phenylcarbonyl, Heterocyclyl, Heterocycly-C1-C4-alkyl oder Heterocyclylcarbonyl, wobei der Phenyl- oder Heterocyclyl-Rest der sechs letztgenannten Substituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy oder C1-C4-Halogenalkoxy;Phenyl, phenyl-C 1 -C 4 -alkyl, phenylcarbonyl, heterocyclyl, heterocycly-C 1 -C 4 -alkyl or heterocyclylcarbonyl, where the phenyl or heterocyclyl radical of the six last-mentioned substituents can be partially or completely halogenated and / or one can carry up to 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;
R16,R17 unabhängig voneinander Wasserstoff, C1-C6-Alkyl, C3-C6-Alkenyl oder C3-C6-Alkinyl bedeuten;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;
sowie deren landwirtschaftlich brauchbaren Salze.and their agriculturally useful salts.
Ferner wurden herbizide Mittel gefunden, die Cyclohexenon-Derivate der Formel I enthalten und eine sehr gute herbizide Wirkung besitzen. Außerdem wurden Verfahren zur Herstellung dieser Mittel und Verfahren zur Bekämpfung von unerwünschtem Pflanzenwuchs mit den Cyclohexenon-Derivaten der Formel I gefunden.In addition, herbicidal compositions have been found which contain cyclohexenone derivatives of the formula I and have a very good herbicidal action. We have also found processes for the preparation of these compositions and processes for controlling undesirable vegetation using the cyclohexenone derivatives of the formula I.
Die Verbindungen der Formel I können je nach Substitutionsmuster ein oder mehrere Chiralitätszentren enthalten und liegen dann als Enantiomeren oder Diastereomerengemische vor. Gegenstand der Er- findung sind sowohl die reinen Enantiomeren oder Diastereomeren als auch deren Gemische.Depending on the substitution pattern, 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.
Die Verbindungen der Formel I können auch in Form ihrer landwirtschaftlich brauchbaren Salze vorliegen, wobei es auf die Art des Salzes in der Regel nicht ankommt. Im Allgemeinen kommen dieThe 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
Salze derjenigen Kationen oder die Säureadditionssalze derjenigen Säuren in Betracht, deren Kationen, beziehungsweise Anionen, die herbizide Wirkung der Verbindungen I nicht negativ beeinträchtigen. Es kommen als Kationen insbesondere Ionen der Alkalimetalle, vorzugsweise Lithium, Natrium und Kalium, der Erdalkalimetalle, vorzugsweise Calcium und Magnesium, und der Übergangsmetalle, vorzugsweise Mangan, Kupfer, Zink und Eisen, sowie Ammonium, wobei hier gewunschtenfalls ein bis vier Wasserstoffatome durch C1-C4—Alkyl, Hydroxy-C1-C4—alkyl, C1-C4-Alkoxy-C1-C4-alkyl, Hydroxy-C1-C4-alkoxy-C1-C4-alkyl, Phenyl oder Benzyl ersetzt sein können, vorzugsweise Ammonium, Dimethylammonium, Diisopropylammonium, Tetramethylammonium, Tetrabutylammonium, 2- ( 2-Hydroxyeth-l-oxy)eth-l-ylammonium,Salts of those cations or the acid addition salts of those acids whose cations or anions do not adversely affect the herbicidal activity of the compounds I. 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-hydroxyeth-l-oxy) eth-l-ylammonium,
Di( 2-hydroxyeth-l-yl)ammonium, Trimethylbenzylammonium, des weiteren Phosphoniumionen, Sulfoniumionen, vorzugsweise Tri(C1—C4—alkyl) sulfonium und Sulfoxoniumionen, vorzugsweise Tri( C1-C4—alkyl )sulfoxonium, in Betracht.Di (2-hydroxyeth-l-yl) ammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri (C 1 -C 4 alkyl) sulfonium and sulfoxonium ions, preferably tri (C 1 -C 4 alkyl) sulfoxonium, into consideration ,
Anionen von brauchbaren Säureadditionsalzen sind in erster Linie Chlorid, Bromid, Fluorid, Hydrogensulfat, Sulfat, Dihydrogenphosphat, Hydrogenphosphat, Nitrat, Hydrogencarbonat, Carbonat, Hexafluorosilikat, Hexafluorophosphat, Benzoat sowie die Anionen von C1-C4—Alkansäuren, vorzugsweise Formiat, Acetat, Propionat und Butyrat.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.
Im Falle von R4 = Hydroxy oder Mercapto {Y = 0, S} steht Ha auch stellvertretend für die tautomeren Formen IIa', IIa' ' und IIa' ' ' .In the case of R 4 = hydroxy or mercapto {Y = 0, S}, Ha also represents the tautomeric forms IIa ', IIa''andIIa'''.
Figure imgf000008_0001
beziehungsweise Ilb auch stellvertretend für die tautomeren Formen Ilb', Ilb'' und Ilb'''.
Figure imgf000009_0001
Figure imgf000008_0001
and Ilb also represent the tautomeric forms Ilb ', Ilb''andIlb'''.
Figure imgf000009_0001
Die für die Substituenten R1 bis R16 oder als Reste an Phenyl— und Heterocyclyl—Resten genannten organischen Molekülteile stellen Sammelbegriffe für individuelle Aufzählungen der einzelnen Gruppenmitglieder dar. Sämtliche Kohlenwasserstoffketten, also alle Alkyl—, Halogenalkyl—, Alkoxy—, Halogenalkoxy—, Alkylthio—, Halogenalkylthio—, Alkylsulfinyl—, Halogenalkylsulfinyl—, Alkylsulfonyl—, Halogenalkylsulfonyl—, N-Alkylamino-, N,N-Dialkylamino-, N-Halogenalkylamino-, N-Alkoxyamino- , N-Alkoxy-N-alkylamino-, N-Alkylcarbonylamino-, Alkylcarbonyl—, Halogenalkylcarbonyl, Alkoxycarbonyl—, Halogenalkoxycarbonyl, Alkylthiocarbonyl-, Alkylcarbonyloxy—, Alkylaminocarbonyl—, Dialkylaminocarbonyl—, Dialkylaminothiocarbonyl-, Alkoxyalkyl—, Alkoxyiminoalkyl- , Phenylalkylcarbonyl , Heterocyclylalkylcarbonyl, Phenylalkenylcarbonyl-,The organic parts of the molecule mentioned for the substituents R 1 to R 16 or as residues on phenyl and heterocyclyl residues are collective terms for individual lists of the individual group members. All hydrocarbon chains, ie all alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio -, haloalkylthio—, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, N-alkylamino, N, N-dialkylamino, N-haloalkylamino, N-alkoxyamino, N-alkoxy-N-alkylamino, N- Alkylcarbonylamino, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, alkylthiocarbonyl, alkylcarbonyloxy, alkylaminocarbonyl, dialkylaminocarbonyl, dialkylaminothiocarbonyl, alkoxyalkyl, alkoxyiminoalkyl, phenylalkylcarbonyl, heterocyclyalkylcarbonyl, carbonyl
Heterocyclylalkenylcarbonyl- , N—Alkoxy—N—alkylaminocarbonyl—, N—Alkyl—N—phenylaminocarbonyl—,Heterocyclylalkenylcarbonyl-, N-alkoxy-N-alkylaminocarbonyl, N-alkyl-N-phenylaminocarbonyl,
N—Alkyl—N—heterocyclylaminocarbonyl—, Phenylalkyl—, Heterocyclylalkyl—, Phenylcarbonylalkyl—, Heterocyclylcarbonylalkyl—, Alkoxyalkoxycarbonyl—,N — alkyl — N — heterocyclylaminocarbonyl, phenylalkyl, heterocyclylalkyl, phenylcarbonylalkyl, heterocyclylcarbonylalkyl, alkoxyalkoxycarbonyl,
Alkenylcarbonyl—, Alkenyloxycarbonyl—, Alkenylaminocarbonyl—, N—Alkenyl—N—alkylaminocarbonyl—,Alkenylcarbonyl—, alkenyloxycarbonyl—, alkenylaminocarbonyl—, N — alkenyl — N — alkylaminocarbonyl—,
N—Alkenyl—N—alkoxyaminocarbonyl—, Alkinylcarbonyl—, Alkinyloxycarbonyl—, Alkinylaminocarbonyl—, N—Alkinyl—N—alkylaminocarbonyl—,N — alkenyl — N — alkoxyaminocarbonyl—, alkynylcarbonyl, alkynyloxycarbonyl, alkynylaminocarbonyl, N — alkynyl — N — alkylaminocarbonyl,
N—Alkinyl—N—alkoxyaminocarbonyl—, Alkenyl—, Alkinyl—, Halogenalkenyl—, Halogenalkinyl—, Alkenyloxy-, Alkinyloxy, Alkandiyl-, Alkendiyl-, Alkadiendiyl- oder Alkindiyl— eile können geradkettig oder verzweigt sein. Sofern nicht anders angegeben tragen halogenierte Substituenten vorzugsweise ein bis fünf gleiche oder verschiedene Halogenatome. Die Bedeutung Halogen steht jeweils für Fluor, Chlor, Brom oder Iod.N — alkynyl — N — alkoxyaminocarbonyl, alkenyl, alkynyl, haloalkenyl, haloalkynyl, alkenyloxy, alkynyloxy, alkanediyl, alkenediyl, alkadienediyl or alkynediyl parts can be straight-chain or branched. Unless otherwise stated, halogenated substituents preferably carry one to five same or different halogen atoms. Halogen is fluorine, chlorine, bromine or iodine.
Ferner bedeuten beispielsweise:Furthermore, for example:
— C1-C4—Alkyl: z.B. Methyl, Ethyl, Propyl, 1-Methylethyl, Butyl, 1—Methylpropyl, 2—Methylpropyl oder 1, 1—Dimethylethyl;C 1 -C 4 alkyl: for example methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl or 1, 1-dimethylethyl;
— C1-C6—Alkyl, sowie die Alkylteile von C1-C6—Alkylamino, Di- (C1-C6-alkyl )amino , N- (C1-C6-Alkoxy) -N- (C1-C6-alkyl ) amino , N(C1-C6—Alkoxy)—N-(C1—C6—alkyl)—aminocarbonyl, N-(C3-C6-Alkenyl)-N-(C1-C6-alkyl)-aminocarbonyl, N- ( C3-C6-Alkinyl )—N—(C1-C6-alkyl )—aminocarbonyl , N—(C1-C6—Alkyl )—N—phenylaminocarbonyl, N—(C1-C6—Alkyl)—N—heterocyclylaminocarbonyl: C1-C4—Alkyl, wie voranstehend genannt, sowie z.B. Pentyl, 1—Methylbutyl, 2-Methylbutyl, 3-Methylbutyl, 2,2-Dimethylpropyl, 1—Ethylpropyl, Hexyl, 1 , 1—Dimethylpropyl , 1 , 2—Dimethylpropyl, 1—Methylpentyl, 2—Methylpentyl, 3—Methylpentyl, 4—Methylpentyl, 1, 1—Dimethylbutyl, 1,2—Dimethylbutyl,- 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 — methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2- Dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1,2-dimethylbutyl,
1 , 3—Dimethylbutyl , 2, 2-Dimethylbutyl, 2 , 3—Dimethylbutyl , 3,3-Dimethylbutyl, 1-Ethylbutyl , 2-Ethylbutyl, 1,1, 2—Trimethylpropyl , 1—Ethyl—1—methylpropyl oder 1—Ethyl—3—methylpropyl ;1, 3-dimethylbutyl, 2, 2-dimethylbutyl, 2, 3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1, 2-trimethylpropyl, 1-ethyl-1-methylpropyl or 1- Ethyl-3-methylpropyl;
— C1-C4—Halogenalkyl: einen C1-C4—Alkylrest , wie vorstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder Iod substituiert ist, also z.B. Chlormethyl, Dichlormethyl, Trichlormethyl, Fluormethyl, Difluormethyl, Trifluormethyl, Chlorfluormethyl, Dichlorfluormethyl,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,
Chlordifluormethyl, 2-Fluorethyl, 2-Chlorethyl, 2-Bromethyl, 2-Iodethyl, 2,2-Difluorethyl, 2 ,2 , 2-Trifluorethyl, 2-Chlor-2-fluorethyl , 2-Chlor-2 , 2-difluorethyl , 2 , 2-Dichlor-2-fluorethyl , 2,2, 2-Trichlorethyl , Pentafluorethyl, 2-Fluorpropyl, 3-Fluorpropyl,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,
2,2-Difluorpropyl, 2, 3-Difluorpropyl, 2-Chlorpropyl, 3-Chlorpropyl, 2 , 3-Dichlorpropyl, 2-Brompropyl, 3-Brompropyl, 3,3, 3-Trifluorpropyl , 3,3, 3-Trichlorpropyl, 2,2,3,3, 3-Pentafluorpropyl , Heptafluorpropyl , l-(Fluormethyl)-2-fluorethyl, l-(Chlormethyl )-2-chlorethyl, 1- (Brommethyl) -2-bromethyl, 4-Fluorbutyl, 4-Chlorbutyl, 4-Brombutyl oder Nonafluorbutyl;2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3, 3-trifluoropropyl, 3,3, 3-trichloropropyl, 2,2,3,3, 3-pentafluoropropyl, heptafluoropropyl, l- (fluoromethyl) -2-fluoroethyl, l- (chloromethyl) -2-chloroethyl, 1- (bromomethyl) -2-bromethyl, 4-fluorobutyl, 4- Chlorobutyl, 4-bromobutyl or nonafluorobutyl;
— C1-C6—Halogenalkyl, sowie die Halogenalkylteile von N-C1-C6-Halogenalkylamino: C1-C4—Halogenalkyl, wie voranstehend genannt, sowie z.B. 5—Fluorpentyl,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,
5—Chlorpentyl , 5—Brompen l odpentyl, Undecafluorpentyl, 6—Fluorhexyl, 6-Chlorhexyl, 6—Bromhexyl, 6—Iodhexyl oder Dodecafluorhexyl ;5 — chloropentyl, 5 — bromophenodpentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl or dodecafluorohexyl;
— C1—C4— lkoxy: z.B. Methoxy, Ethoxy, Propoxy, 1—Methylethoxy, Butoxy, 1—Methylpropoxy, 2—Methylpropoxy oderC 1 -C 4 -alkoxy: for example methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or
1 , 1—Dirnethylethoxy,1, 1-dirnethylethoxy,
— C1-C6—Alkoxy, sowie die Alkoxyteile von N-C1-C6-Alkoxyamino, N- ( C1-C6-Alkoxy) -N- (C1-C6-alkyl ) amino, C1-C6—Alkoxyimino—C1-C6—alkyl,- C 1 -C 6 alkoxy, and the alkoxy parts of NC 1 -C 6 alkoxyamino, N- (C 1 -C 6 alkoxy) -N- (C 1 -C 6 alkyl) amino, C 1 -C 6 -alkoxyimino-C 1 -C 6 -alkyl,
N—(C1-C6—Alkoxy)—N—(C1-C6—alkyl)—aminocarbonyl,N— (C 1 -C 6 alkoxy) —N— (C 1 -C 6 alkyl) aminocarbonyl,
N—(C3—C6—Alkenyl)—N—(C1-C6—alkoxy)—aminocarbonyl undN - (C 3 -C 6 alkenyl) - N - (C 1 -C 6 alkoxy) aminocarbonyl and
N—(C3—C6—Alkinyl)—N—(C1-C6—alkoxy)—aminocarbonyl: C1-C4—Alkoxy, wie voranstehend genannt, sowie z.B. Pentoxy, 1—Methylbutoxy, 2—Methylbutoxy, 3—Methylbutoxy, 1 , 1—Dimethylpropoxy, 1 , 2—Dimethylpropoxy,N— (C 3 -C 6 -alkynyl) —N— (C 1 -C 6 -alkoxy) -aminocarbonyl: C 1 -C 4 -alkoxy, as mentioned above, and also, for example, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1, 1-dimethylpropoxy, 1, 2-dimethylpropoxy,
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-Ethylbutoxy, 1, 1 , 2-Trimethylpropoxy, 1, 2 , 2-Trimethylpropoxy, 1-Ethyl-l-methylpropoxy oder 1-Ethyl—2-methylpropoxy;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-ethylbutoxy, 1, 1, 2-trimethylpropoxy, 1, 2, 2-trimethylpropoxy, 1-ethyl-l-methylpropoxy or 1-ethyl— 2-methylpropoxy;
— C1-C4—Halogenalkoxy: einen C1—C4—Alkoxyrest, wie voranstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder Iod substituiert ist, also z.B. Fluormethoxy, Difluormethoxy, Trifluormethoxy, Chlordifluormethoxy, Bromdifluormethoxy, 2—Fluorethoxy, 2-Chlorethoxy, 2—Bromethoxy, 2—Iodethoxy, 2 ,2—Difluorethoxy, 2,2, 2—Trifluorethoxy, 2—Chlor—2—fluorethoxy, 2-Chlor-2 , 2-difluorethoxy, 2 , 2-Di-chlor-2-fluorethoxy, 2,2,2—Trichlorethoxy, Pentafluorethoxy, 2—Fluorpropoxy, 3—Fluorpropoxy, 2-Chlorpropoxy, 3—Chlorpropoxy, 2—Brompropoxy, 3—Brompropoxy, 2,2—Difluorpropoxy, 2 , 3—Difluorpropoxy, 2 , 3—Dichlorpropoxy, 3,3, 3—Trifluorpropoxy, 3, 3 , 3-Trichlorpropoxy, 2,2,3,3, 3—Pentafluorpropoxy, Heptafluorpropoxy, 1—(Fluormethyl)—2—fluorethoxy, 1—(Chlormethyl)—2—chlorethoxy, 1—(Brommethyl)—2—bromethoxy, 4—Fluorbutoxy, 4—Chlorbutoxy, 4—Brombutoxy oder Nonafluorbutoxy;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-bromopropoxy, 3-bromopropoxy, 2,2-difluoropropoxy , 2,3-difluoropropoxy, 2,3-dichloropropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy, 1- (fluoromethyl) -2 -Fluoroethoxy, 1- (chloromethyl) -2-chloroethoxy, 1- (bromomethyl) -2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy;
— C1-C6—Halogenalkoxy: C1-C4—Halogenalkoxy, wie voranstehend genannt, sowie z.B. 5—Fluorpentoxy, 5—Chlorpentoxy, 5—Brompentoxy, 5—Iodpentoxy, Undecafluorpentoxy, 6—Fluorhexoxy, 6—Chlorhexoxy, 6—Bromhexoxy, 6—lodhexoxy oder Dodecafluor exoxy;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;
— C1-C4—Alkylthio (C1-C4-Alkylsulfanyl: C1-C4-Alkyl-S- ) : z.B. Methylthio, Ethylthio, Propylthio, 1—Methylethylthio,C 1 -C 4 alkylthio (C 1 -C 4 alkylsulfanyl: C 1 -C 4 alkyl-S-): for example methylthio, ethylthio, propylthio, 1-methylethylthio,
Butylthio, 1—Methylpropylthio, 2—Methylpropylthio oder 1, 1—Dimethylethylthio;Butylthio, 1-methylpropylthio, 2-methylpropylthio or 1, 1-dimethylethylthio;
— C1-C6—Alkylthio, sowie die Alkylthioteile von C1-C6-Alkylthiocarbonyl: C1-C4—Alkylthio, wie voranstehend genannt, sowie z.B. 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—Dimethylbutylthio, 1 , 2—Dimethylbutylthio, 1 , 3—Dimethylbutylthio, 2 , 2—Dimethylbutylthio, 2 , 3—Dimethylbutylthio, 3 , 3—Dimethylbutylthio, 1-Ethylbutylthio, 2-Ethylbutylthio, 1, 1, 2—Trimethylpropylthio, 1,2,2— rimethylpropylthio,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-ethylbutylthio, 1, 1, 2-trimethylpropylthio, 1,2,2-rimethylpropylthio,
1—Ethyl—1—methylpropylthio oder 1—Ethyl—2—methylpropylthio;1-ethyl-1-methylpropylthio or 1-ethyl-2-methylpropylthio;
— C1-C4—Halogenalkylthio: einen C1-C4—Alkylthiorest, wie voranstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder Iod substituiert ist, also z.B. Fluormethylthio, Difluormethylthio, Trifluormethylthio, Chlordifluormethylthio, Bromdifluormethylthio, 2—Fluorethylthio, 2—Chlorethylthio, 2—Bromethylthio, 2—Iodethylthio, 2 , 2—Difluorethylthio, 2, 2, 2-Trifluorethylthio, 2 , 2, 2-Trichlorethylthio,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-Chlor-2-fluorethylthio, 2-Chlor-2 , 2-difluorethylthio, 2 , 2—Dichlor—2—fluorethylthio, Pentafluorethylthio, 2—Fluorpropylthio, 3—Fluorpropylthio, 2—Chlorpropylthio, 3—Chlorpropylthio, 2—Brompropylthio, 3—Brompropylthio, 2 , 2—Difluorpropylthio, 2, 3—Difluorpropylthio,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,
2 , 3—Dichlorpropylthio, 3,3, 3—Trifluorpropylthio, 3,3, 3—Tri-chlorpropylthio, 2,2,3,3, 3—Pentafluorpropylthio, Heptafluorpropylthio, 1—(Fluormethyl)—2—fluorethylthio, 1—(Chlormethyl)—2—chlorethylthio, 1—(Brommethyl)—2—bromethylthio, 4—Fluorbutylthio,2,3-dichloropropylthio, 3,3,3-trifluoropropylthio, 3,3,3-tri-chloropropylthio, 2,2,3,3,3-pentafluoropropylthio, heptafluoropropylthio, 1- (fluoromethyl) -2-fluoroethylthio, 1- (Chloromethyl) -2-chloroethylthio, 1- (bromomethyl) -2-bromethylthio, 4-fluorobutylthio,
4—Chlorbutylthio, 4—Brombutylthio oder Nonafluorbutylthio;4 — chlorobutylthio, 4 — bromobutylthio or nonafluorobutylthio;
C1-C6-Halogenalkylthio: C1-C4-Halogenalkylthio, wie vorstehend genannt, sowie 5—Fluorpentylthio, 5—Chlorpentylthio, 5—Brompentylthio, 5—Iodpentylthio, Undecafluorpentylthio, 6—Fluorhexylthio, 6—Chlorhexylthio, 6—Bromhexylthio, 6—Iodhexylthio oder Dodecafluorhexylthio;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;
- C1-C4-Alkylsulfinyl ( C1-C4-Alkyl-S(=0)-) : z.B. Methylsulfinyl , Ethylsulfinyl, Propylsulfinyl, 1—Methylethylsulfinyl,C 1 -C 4 -alkylsulfinyl (C 1 -C 4 -alkyl-S (= 0) -): for example methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl,
Butylsulfinyl, 1—Methylpropylsulfinyl, 2—Methylpropylsulfinyl oder 1, 1—Dimethylethylsulfinyl;Butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl or 1, 1-dimethylethylsulfinyl;
C1-C6-Alkylsulfinyl: C1-C4-Alkylsulfinyl, wie vorstehend genannt, sowie 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,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—Ethylbutylsulfinyl , 2-Ethylbutylsulfinyl, 1, 1, 2-Trimethylpropylsulfinyl,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,
1,2, 2—Trimethylpropylsulfinyl , 1—Ethyl—1—methylpropylsulfinyl oder 1—Ethyl—2—methylpropylsulfinyl;1,2, 2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl or 1-ethyl-2-methylpropylsulfinyl;
— C1—C4—Halogenalkylsulfinyl: C1-C4—Alkylsulfinylrest, wie voranstehend genannt, der partiell oder vollständig durch- C 1 -C 4 -Halogenalkylsulfinyl: C 1 -C 4 -Alkylsulfinylrest, as mentioned above, the partially or completely by
Fluor, Chlor, Brom und/oder Iod substituiert ist, also z.B.Fluorine, chlorine, bromine and / or iodine is substituted, e.g.
Fluormethylsulfinyl, Difluormethylsulfinyl ,Fluoromethylsulfinyl, difluoromethylsulfinyl,
Trifluormethylsulfinyl , Chlordifluormethylsulfinyl,Trifluoromethylsulfinyl, chlorodifluoromethylsulfinyl,
Bromdifluormethylsulfinyl , 2—Fluorethylsulfinyl , 2—Chlorethylsulfinyl, 2-Bromethylsulfinyl,Bromodifluoromethylsulfinyl, 2 — fluoroethylsulfinyl, 2 — chloroethylsulfinyl, 2-bromoethylsulfinyl,
2—Iodethylsulfinyl , 2 , 2-Difluorethylsulfinyl ,2-iodoethylsulfinyl, 2, 2-difluoroethylsulfinyl,
2,2, 2-Trifluorethylsulfinyl , 2,2, 2-Trichlorethylsulfinyl ,2,2,2-trifluoroethylsulfinyl, 2,2,2-trichloroethylsulfinyl,
2-Chlor-2-fluorethylsulfinyl,2-chloro-2-fluorethylsulfinyl,
2—Chlor—2 , 2—difluorethylsulfinyl, 2, 2—Dichlor—2—fluorethylsulfinyl, Pentafluorethylsulfinyl,2-chloro-2,2-difluoroethylsulfinyl, 2,2-dichloro-2-fluoroethylsulfinyl, pentafluoroethylsulfinyl,
2—Fluorpropylsulfinyl , 3—Fluorpropylsulfinyl ,2 — fluoropropylsulfinyl, 3 — fluoropropylsulfinyl,
2—Chlorpropylsulfinyl , 3—Chlorpropylsulfinyl,2-chloropropylsulfinyl, 3-chloropropylsulfinyl,
2—Brompropylsulfinyl , 3—Brompropylsulfinyl ,2-bromopropylsulfinyl, 3-bromopropylsulfinyl,
2 , 2—Difluorpropylsulfinyl, 2 , 3—Difluorpropylsulfinyl, 2, 3—Dichlorpropylsulfinyl, 3 , 3, 3—Trifluorpropylsulfinyl,2, 2-difluoropropylsulfinyl, 2, 3-difluoropropylsulfinyl, 2, 3-dichloropropylsulfinyl, 3, 3, 3-trifluoropropylsulfinyl,
3,3, 3—Trichlorpropylsulfinyl,3,3,3-trichloropropylsulfinyl,
2,2,3,3, 3—Pentafluorpropylsulfinyl , Heptafluorpropylsulfinyl ,2,2,3,3, 3-pentafluoropropylsulfinyl, heptafluoropropylsulfinyl,
1—(Fluormethyl )—2—fluorethylsulfinyl,1- (fluoromethyl) -2-fluoroethylsulfinyl,
1—(Chlormethyl)—2-chlorethylsulfinyl, 1—(Brommethyl)—2—bromethylsulfinyl, 4—Fluorbutylsulfinyl, 4—Chlorbutylsulfinyl, 4—Brombutylsulfinyl oder Nonafluorbutylsulfinyl ;1- (chloromethyl) -2-chloroethylsulfinyl, 1- (bromomethyl) -2-bromomethylsulfinyl, 4-fluorobutylsulfinyl, 4-chlorobutylsulfinyl, 4-bromobutylsulfinyl or nonafluorobutylsulfinyl;
C1-C6-Halogenalkylsulfinyl : C1-C4-Halogenalkylsulfinyl, wie vorstehend genannt, sowie 5—Fluorpentylsulfinyl, 5—Chlorpentylsulfinyl , 5—Brompentylsulfinyl , 5—Iodpentylsulfinyl, Undecafluorpentylsulfinyl , 6—Fluorhexylsulfinyl , 6—Chlorhexylsulfinyl , 6—Bromhexylsulfinyl, 6—Iodhexylsulfinyl oder Dodecafluorhexylsulfinyl;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;
- C1-C4-Alkylsulfonyl (C1-C4-Alkyl-S (=O) 2-) : z.B. Methylsulfonyl, Ethylsulfonyl, Propylsulfonyl,C 1 -C 4 alkylsulfonyl (C 1 -C 4 alkyl-S (= O) 2 -): for example methylsulfonyl, ethylsulfonyl, propylsulfonyl,
1—Methylethylsulfonyl, Butylsulfonyl, 1—Methylpropylsulfonyl, 2—Methylpropylsulfonyl oder 1, 1—Dimethylethylsulfonyl;1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl or 1,1-dimethylethylsulfonyl;
C1-C6-Alkylsulfonyl: C1-C4-Alkylsulfonyl, wie vorstehend genannt, sowie Pentylsulfonyl, 1—Methylbutylsulfonyl, 2—Methylbutylsulfonyl , 3—Methylbutylsulfonyl , 1, 1—Dimethylpropylsulfonyl, 1, 2—Dimethylpropylsulfonyl, 2 , 2—Dimethylpropylsulfonyl , 1—Ethylpropylsulfonyl , Hexylsulfonyl , 1—Methylpentylsulfonyl , 2—Methylpentylsulfonyl , 3—Methylpentylsulfonyl , 4— ethylpentylsulfonyl , 1 , 1—Dimethylbutylsulfonyl, 1, 2—Dimethylbutylsulfonyl, 1 , 3—Dimethylbutylsulfonyl, 2 , 2—Dimethylbutylsulfonyl , 2 , 3—Dimethylbutylsulfonyl, 3 , 3—Dimethylbutylsulfonyl, 1—Ethylbutylsulfonyl, 2—Ethylbutylsulfonyl , 1,1, 2-Trimethylpropylsulfonyl, 1,2, 2—Trimethylpropylsulfonyl , 1—Ethyl—1—methylpropylsulfonyl oder 1—Ethyl—2—methylpropylsulfonyl;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-sulfylylsulfonyl, 1, 2-dimethylbutyl, 2-sulfylylsulfonyl, 1 , 3-dimethylbutylsulfonyl, 3, 3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1, 2-trimethylpropylsulfonyl, 1,2, 2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfylylonyl or 1-methyl ;
— C1-C4—Halogenalkylsulfonyl : einen C1-C4—Alkylsulfonylrest, wie voranstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder Iod substituiert ist, also z.B. Fluormethylsulfonyl, Difluormethylsulfonyl,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,
Trifluormethylsulfonyl, Chlordifluormethylsulfonyl, Bromdifluormethylsulfonyl , 2—Fluorethylsulfonyl , 2—Chlorethylsulfonyl, 2—Bromethylsulfonyl, 2—Iodethylsulfonyl , 2 , 2—Difluorethylsulfonyl , 2, 2, 2-Trifluorethylsulfonyl, 2-Chlor-2-fluorethylsulfonyl, 2-Chlor-2 , 2-difluorethylsulfonyl , 2 , 2—Dichlor—2—fluorethylsulfonyl ,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—Trichlorethylsulfonyl , Pentafluorethylsulfonyl, 2—Fluorpropylsulfonyl , 3—Fluorpropylsulfonyl , 2—Chlorpropylsulfonyl, 3—Chlorpropylsulfonyl, 2—Brompropylsulfonyl, 3—Brompropylsulfonyl, 2 , 2—Difluorpropylsulfonyl fluorpropylsulfonyl , 2 , 3—Dichlorpropylsulfonyl, 3,3, 3—Trifluorpropylsulfonyl , 3,3, 3—Trichlorpropylsulfonyl ,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,
2,2,3,3, 3—Pentafluorpropylsulfonyl, Heptafluorpropylsulfonyl , 1—( Fluormethyl )—2—fluorethylsulfonyl , 1—( Chlormethyl )—2—chlorethylsulfonyl ,2,2,3,3, 3-pentafluoropropylsulfonyl, heptafluoropropylsulfonyl, 1- (fluoromethyl) -2-fluoroethylsulfonyl, 1- (chloromethyl) -2-chloroethylsulfonyl,
1—( Brommethyl )—2— romethylsulfonyl , 4—Fluorbutylsulfonyl , 4—Chlorbutylsulfonyl, 4—Brombutylsulfonyl oder Nonafluorbutylsulfonyl;1- (bromomethyl) -2-romethylsulfonyl, 4-fluorobutylsulfonyl, 4-chlorobutylsulfonyl, 4-bromobutylsulfonyl or nonafluorobutylsulfonyl;
- C1-C6-Halogenalkylsulfonyl: C1-C4-Halogenalkylsulfonyl , wie vorstehend genannt, sowie 5—Fluorpentylsulfonyl,C 1 -C 6 haloalkylsulfonyl: C 1 -C 4 haloalkylsulfonyl, as mentioned above, and 5-fluoropentylsulfonyl,
5—Chlorpentylsulfonyl , 5—Brompentylsulfonyl ,5 — chloropentylsulfonyl, 5 — bromopentylsulfonyl,
5—Iodpentylsulfonyl , 6—Fluorhexylsulfonyl,5 — iodopentylsulfonyl, 6 — fluorohexylsulfonyl,
6—Bromhexylsulfonyl, 6—Iodhexylsulfonyl oder Dodecafluorhexylsulfonyl;6-bromohexylsulfonyl, 6-iodohexylsulfonyl or dodecafluorohexylsulfonyl;
— C1-C6-Alkylamino: Methylamino, Ethylamino, Propylamino, 1-Methylethylamino, Butylamino, 1-Methylpropylamino, 2-Methylpropylamino, 1, 1-Dimethylethylamino, Pentylamino, 1-Methylbutylamino, 2-Methylbutylamino, 3-Methylbutylamino, 2, 2-Dimethylpropylamino, 1-Ethylpropylamino, Hexylamino, 1 , 1-Dimethylpropylamino, 1 , 2-Dimethylpropylamino, 1-Methylpentylamino, 2-Methylpentylamino, 3-Methylpentylamino, 4-Methylpentylamino, 1, 1-Dimethylbutylamino, 1, 2-Dimethylbutylamino, 1, 3-Dimethylbutylamino, 2, 2-Dimethylbutylamino, 2 , 3-Dimethylbutylamino, 3 , 3-Dimethylbutylamino, 1-Ethylbutylamino, 2-Ethylbutylamino, 1,1, 2-Trimethylpropylamino, 1,2, 2-Trimethylpropylamino, 1-Ethyl-l-methylpropylamino oder l-Ethyl-2-methylpropylamino;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-dimethylbutylamino, 1-ethylbutylamino, 2-ethylbutylamino, 1,1, 2-trimethylpropylamino, 1,2, 2-trimethylpropylamino, 1 -Ethyl-l-methylpropylamino or l-ethyl-2-methylpropylamino;
Di- (C1-C4-alkyl) amino: z.B. N,N-Dimethylamino,Di- (C 1 -C 4 alkyl) amino: for example N, N-dimethylamino,
N,N-Di-ethylamino, N,N-Dipropylamino,N, N-di-ethylamino, N, N-dipropylamino,
N,N-Di—( 1-methylethyl) amino, N,N-Dibutylamino, N,N-Di-( 1-methylpropyl) amino, N,N-Di-( 2-methylpropyl) amino,N, N-di- (1-methylethyl) amino, N, N-dibutylamino, N, N-di- (1-methylpropyl) amino, N, N-di- (2-methylpropyl) amino,
N, -Di- ( 1 , 1—dimethylethyl ) amino, N-Ethyl-N—methylamino,N, -Di- (1, 1-dimethylethyl) amino, N-ethyl-N-methylamino,
N-Methyl-N-propylamino, N-Methyl-N- ( 1-methylethyl ) amino,N-methyl-N-propylamino, N-methyl-N- (1-methylethyl) amino,
N-Butyl-N-methylamino, N-Methyl-N- ( 1-methylpropyl )amino,N-butyl-N-methylamino, N-methyl-N- (1-methylpropyl) amino,
N-Methyl-N- ( 2-methylpropyl ) amino, N-( 1 , l-Di-methylethyl)-N-methylamino, N-Ethyl-N-propylamino,N-methyl-N- (2-methylpropyl) amino, N- (1, l-dimethylethyl) -N-methylamino, N-ethyl-N-propylamino,
N-Ethyl-N- ( 1-methylethyl ) amino, N-Butyl-N-ethylamino,N-ethyl-N- (1-methylethyl) amino, N-butyl-N-ethylamino,
N-Ethyl-N- ( 1-methylpropyl ) amino,N-ethyl-N- (1-methylpropyl) amino,
N-Ethyl-N-( 2-methylpropyl ) amino,N-ethyl-N- (2-methylpropyl) amino,
N-Ethyl-N- ( 1 , 1-dimethylethyl ) amino, N-( l-Methylethyl)-N-propylamino, N-Butyl-N-propylamino,N-ethyl-N- (1,1-dimethylethyl) amino, N- (l-methylethyl) -N-propylamino, N-butyl-N-propylamino,
N- ( 1-Methylpropyl ) -N-propylamino,N- (1-methylpropyl) -N-propylamino,
N- ( 2-Methylpropyl ) -N-prop l i N- ( 1 , 1-Dimethylethyl ) -N-propylamino, N-Butyl-N- ( 1-methylethyl ) amino, N-( 1-Methylethyl) -N-( 1-methylpropyl ) amino, N-( l-Methylethyl)-N-( 2-methylpropyl ) amino, N- ( 1 , 1-Dimethylethyl ) -N- ( 1-methylethyl ) amino, N-Butyl-N-( 1-methylpropyl)—amino, N-Butyl-N- ( 2-methylpropyl) amino, N-Butyl-N-( 1 , 1—dimethylethyl ) amino, N- ( 1-Methylpropyl ) -N- ( 2-methylpropyl )—amino, N-( 1 , 1-Dimethylethyl )-N-( 1-methylpropyl)—amino oder N-( 1 , 1-Dimethylethyl )-N-( 2-methylpropyl ) amino;N- (2-methylpropyl) -N-prop li N- (1, 1-dimethylethyl) -N-propylamino, N-butyl-N- (1-methylethyl) amino, N- (1-methylethyl) -N- (1-methylpropyl) amino, N- (l-methylethyl ) -N- (2-methylpropyl) amino, N- (1, 1-dimethylethyl) -N- (1-methylethyl) amino, N-butyl-N- (1-methylpropyl) amino, N-butyl-N- (2-methylpropyl) amino, N-butyl-N- (1,1-dimethylethyl) amino, N- (1-methylpropyl) -N- (2-methylpropyl) amino, N- (1,1-dimethylethyl) - N- (1-methylpropyl) amino or N- (1, 1-dimethylethyl) -N- (2-methylpropyl) amino;
Di- (C1-C6-alkyl) amino: Di- (C1-C4-alkyl ) amino wie voranstehend genannt, sowie N,N-Dipentylamino, N,N-Dihexylamino, N-Methyl-N-pentylamino, N-Ethyl-N-pentylamino,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,
N-Methyl-N-hexylamino oder N-Ethyl-N-hexylamino;N-methyl-N-hexylamino or N-ethyl-N-hexylamino;
— C1-C4—Alkylcarbonyl: z.B. Methylcarbonyl, Ethylcarbonyl, Propylcarbonyl, 1—Methylethylcarbonyl, Butylcarbonyl, 1—Methylpropylcarbonyl, 2—Methylpropylcarbonyl oder 1 , 1—Dimethylethylcarbonyl ;C 1 -C 4 alkylcarbonyl: for example methylcarbonyl, ethylcarbonyl, propylcarbonyl, 1-methylethylcarbonyl, butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl or 1, 1-dimethylethylcarbonyl;
— C1-C6—Alkylcarbonyl, sowie die Alkylcarbonylreste von C1-C6-Alkylcarbonyl-C1-C6-alkyl , C1-C6-Alkylcarbonylanu.no : C1-C4—Alkylcarbonyl, wie voranstehend genannt, sowie z.B.- C 1 -C 6 -alkylcarbonyl, and the alkylcarbonyl radicals of C 1 -C 6 -alkylcarbonyl-C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonylanu.no: C 1 -C 4 -alkylcarbonyl, as mentioned above , as well as, for example
Pentylcarbonyl, 1—Methylbutylcarbonyl, 2-Methylbutylcarbonyl,Pentylcarbonyl, 1-methylbutylcarbonyl, 2-methylbutylcarbonyl,
3—Methylbutylcarbonyl , 2 , 2-Dimethylpropylcarbonyl ,3 — methylbutylcarbonyl, 2, 2-dimethylpropylcarbonyl,
1—Ethylpropylcarbonyl , Hexylcarbonyl ,1 — ethylpropylcarbonyl, hexylcarbonyl,
1 , 1—Dimethylpropylcarbonyl, 1 , 2—Dimethylpropylcarbonyl, 1—Methylpentylcarbonyl, 2—Methylpentylcarbonyl, 3—Methylpentylcarbonyl, 4—Methylpentylcarbonyl, 1 , 1—Dimethylbutylcarbonyl , 1 , 2—Dimethylbutylcarbonyl , 1 , 3—Dimethylbutylcarbonyl, 2,2 ,—Dimethylbutylcarbonyl, 2 , 3—Dimethylbutylcarbonyl , 3 , 3—Dimethylbutylcarbonyl , 1—Ethylbutylcarbonyl, 2—Ethylbutylcarbonyl,1, 1-Dimethylpropylcarbonyl, 1, 2-Dimethylpropylcarbonyl, 1-Methylpentylcarbonyl, 2-Methylpentylcarbonyl, 3-Methylpentylcarbonyl, 4-Methylpentylcarbonyl, 1, 1-Dimethylbutylcarbonyl, 1, 2-Dimethylbutylcarbonyl, 1, 3-Dimethylbutylcarbonyl, 2,2, —Dimethylbutylcarbonyl, 2, 3 — dimethylbutylcarbonyl, 3, 3 — dimethylbutylcarbonyl, 1 — ethylbutylcarbonyl, 2 — ethylbutylcarbonyl,
1,1, 2—Trimethylpropylcarbonyl , 1,2, 2—Trimethylpropylcarbonyl , 1—Ethyl—1—methylpropylcarbonyl oder 1—Ethyl—2—methylpropylcarbonyl ;1,1,2-trimethylpropylcarbonyl, 1,2,2-trimethylpropylcarbonyl, 1-ethyl-1-methylpropylcarbonyl or 1-ethyl-2-methylpropylcarbonyl;
— C1-C4—Halogenalkylcarbonyl: einen C1-C4—Alkylcarbonylrest, wie vorstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder Iod substituiert ist, also z.B. Chloracetyl, Dichloracetyl, Trichloracetyl, Fluoracetyl, Difluoracetyl, Trifluoracetyl, Chlorfluoracetyl, Dichlor-fluoracetyl, Chlordifluoracetyl,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,
2—Fluorethylcarbonyl , 2-Chlorethylcarbonyl , 2—Bromethylcarbonyl , 2—I arbonyl , 2 , 2—Difluorethylcarbonyl , 2,2, 2—Trifluorethylcarbonyl ,2-fluoroethylcarbonyl, 2-chloroethylcarbonyl, 2-bromoethylcarbonyl, 2-I arbonyl, 2,2-difluoroethylcarbonyl, 2,2,2-trifluoroethylcarbonyl,
2—Chlor—2—fluorethylcarbonyl ,2 — chlorine — 2-fluoroethylcarbonyl,
2-Chlor—2 , 2—difluorethylcarbonyl ,2-chloro-2,2-difluoroethylcarbonyl,
2 , 2—Dichlor—2—fluorethylcarbonyl , 2, 2 , 2—Trichlorethylcarbonyl, Pentafluorethylcarbonyl,2,2-dichloro-2-fluoroethylcarbonyl, 2,2,2-trichloro-ethylcarbonyl, pentafluoroethylcarbonyl,
2—Fluorpropylcarbonyl, 3—Fluorpropylcarbonyl,2 — fluoropropylcarbonyl, 3 — fluoropropylcarbonyl,
2 , 2—Difluorpropylcarbonyl , 2 , 3—Di-fluorpropylcarbonyl ,2,2-difluoropropylcarbonyl, 2,3-di-fluoropropylcarbonyl,
2—Chlorpropylcarbonyl, 3—Chlorpropylcarbonyl ,2 — chloropropylcarbonyl, 3 — chloropropylcarbonyl,
2 , 3—Dichlorpropylcarbonyl , 2—Brompropylcarbonyl , 3—Brompropylcarbonyl, 3, 3 , 3—Trifluorpropylcarbonyl,2, 3-dichloropropylcarbonyl, 2-bromopropylcarbonyl, 3-bromopropylcarbonyl, 3, 3, 3-trifluoropropylcarbonyl,
3,3, 3—Trichlorpropylcarbonyl ,3,3,3-trichloropropylcarbonyl,
2,2,3,3, 3—Pentafluorpropylcarbonyl , Heptafluorpropylcarbonyl,2,2,3,3, 3-pentafluoropropylcarbonyl, heptafluoropropylcarbonyl,
1—( Fluormethyl )—2—fluorethylcarbonyl ,1- (fluoromethyl) -2-fluoroethylcarbonyl,
1—(Chlormethyl)—2—chlorethylcarbonyl, 1—(Brommethyl)—2—bromethylcarbonyl, 4—Fluorbutylcarbonyl,1- (chloromethyl) -2-chloroethylcarbonyl, 1- (bromomethyl) -2-bromethylcarbonyl, 4-fluorobutylcarbonyl,
4—Chlorbutylcarbonyl, 4—Bro butylcarbonyl oder4 — chlorobutylcarbonyl, 4 — bro butylcarbonyl or
Nonafluorbutylcarbonyl ;Nonafluorobutylcarbonyl;
C1-C6-Halogenalkylcarbonyl: einen C1-C4-Halogenalkylcarbonylrest wie voranstehend genannt, sowie 5-Fluorpentylcarbonyl , 5-Chlorpentylcarbonyl , 5-Brompentylcarbonyl , Perfluorpentylcarbonyl , 6-Fluorhexylcarbonyl , 6-Chlorhexylcarbonyl, 6-Bromhexylcarbonyl oder Perfluorhexylcarbonyl;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;
C1-C4—Alkoxycarbonyl : z.B. Methoxycarbonyl, Ethoxycarbonyl, Propoxycarbonyl, 1—Methylethoxycarbonyl, Butoxycarbonyl, 1—Methylpropoxycarbonyl, 2—Methylpropoxycarbonyl oder 1 , 1—Dimethylethoxycarbonyl;C 1 -C 4 alkoxycarbonyl: for example methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, 1-methylethoxycarbonyl, butoxycarbonyl, 1-methylpropoxycarbonyl, 2-methylpropoxycarbonyl or 1, 1-dimethylethoxycarbonyl;
C1-C6-Alkoxycarbonyl: C1-C4—Alkoxycarbonyl, wie vorstehend genannt, sowie z.B. Pentoxycarbonyl, 1-Methylbutoxycarbonyl,C 1 -C 6 alkoxycarbonyl: C 1 -C 4 alkoxycarbonyl, as mentioned above, and also, for example, pentoxycarbonyl, 1-methylbutoxycarbonyl,
2-Methylbutoxycarbonyl, 3-Methylbutoxycarbonyl,2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl,
2, 2-Dimethylpropoxycarbonyl, 1-Ethylpropoxycarbonyl, Hexoxycarbonyl, 1, 1-Dimethylpropoxycarbonyl,2, 2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, hexoxycarbonyl, 1, 1-dimethylpropoxycarbonyl,
1 , 2-Dimethylpropoxycarbonyl , 1-Methylpentoxycarbonyl , 2-Methylpentoxycarbonyl, 3-Methylpentoxycarbonyl, 4-Methylpentoxycarbonyl, 1 , 1-Dimethylbutoxycarbonyl, 1 , 2-Dimethylbutoxycarbonyl, 1 , 3-Dimethylbutoxycarbonyl, 2,2-Dimethylbutoxycarbonyl, 2 , 3-Dimethylbutoxycarbonyl, 3 , 3-Dimethylbutoxycarbonyl , 1-Ethylbutoxycarbonyl , 2-Ethylbutoxycarbonyl , 1,1, 2-Trimethylpropoxycarbonyl , 1,2, 2-Trimethylpropoxycarbonyl , 1-Ethyl-l-methyl-propoxycarbonyl oder l-Ethyl-2-methyl-propoxycarbonyl; — C1-C4—Halogenalkoxycarbonyl: einen C1-C4—Alkoxycarbonylrest , wie voranstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder Iod substituiert ist, also z.B. Fluormethoxycarbonyl, Difluormethoxycarbonyl, Trifluormethoxycarbonyl, Chlordifluormethoxycarbonyl, Bromdifluormethoxycarbonyl , 2—Fluorethoxycarbonyl , 2—Chlorethoxycarbonyl, 2—Bromethoxycarbonyl, 2—Iodethoxycarbonyl , 2 , 2—Difluorethoxycarbonyl , 2,2, 2— rifluorethoxycarbonyl, 2—Chlor—2—fluorethoxycarbonyl, 2—Chlor—2 , 2—difluorethoxycarbonyl, 2 , 2—Dichlor—2—fluorethoxycarbonyl ,1, 2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1, 1-dimethylbutoxycarbonyl, 1, 2-dimethylbutoxycarbonyl, 1, 3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl, 2, 3- Dimethylbutoxycarbonyl, 3, 3-dimethylbutoxycarbonyl, 1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl, 1,1, 2-trimethylpropoxycarbonyl, 1,2, 2-trimethylpropoxycarbonyl, 1-ethyl-l-methyl-propoxycarbonyl or l-ethyl-2-methyl- propoxycarbonyl; 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 fluoromethoxycarbonyl, difluoromethoxycarbonyl, trifluoromethoxycarbonyl, chlorodifluoromethoxycarbonyl, bromodifluoromethoxycarbonyl , 2-fluoroethoxycarbonyl, 2-chloroethoxycarbonyl, 2-bromoethoxycarbonyl, 2-iodoethoxycarbonyl, 2, 2-difluoroethoxycarbonyl, 2,2, 2-rifluoroethoxycarbonyl, 2-chloro-2-fluoroethoxycarbonyl, 2-chloro-2,2, -ifluoroethoxycarbonyl, 2 , 2-dichloro-2-fluoroethoxycarbonyl,
2,2, 2—Trichlorethoxycarbonyl, Pentafluorethoxycarbonyl, 2—Fluorpropoxycarbonyl, 3—Fluorpropoxycarbonyl, 2—Chlorpropoxycarbonyl , 3—Chlorpropoxycarbonyl , 2—Brompropoxycarbonyl, 3—Brompropoxycarbonyl,2,2,2-trichloroethoxycarbonyl, pentafluoroethoxycarbonyl, 2-fluoropropoxycarbonyl, 3-fluoropropoxycarbonyl, 2-chloropropoxycarbonyl, 3-chloropropoxycarbonyl, 2-bromopropoxycarbonyl, 3-bromopropoxycarbonyl,
2 , 2—Difluorpropoxycarbonyl , 2 , 3—Difluorpropoxycarbonyl, 2 , 3—Dichlorpropoxycarbonyl , 3,3, 3— rifluorpropoxycarbonyl , 3,3, 3—Trichlorpropoxycarbonyl, 2,2,3,3, 3—Pentafluorpropoxycarbonyl, Heptafluorpropoxycarbonyl,2,2-difluoropropoxycarbonyl, 2,3-difluoropropoxycarbonyl, 2,3-dichloropropoxycarbonyl, 3,3,3-rifluoropropoxycarbonyl, 3,3,3-trichloropropoxycarbonyl, 2,2,3,3,3, 3-pentafluoropropoxycarbonyl, heptafluoropropoxycarbonyl,
1—( Fluormethyl )—2—fluorethoxycarbonyl,1- (fluoromethyl) -2-fluoroethoxycarbonyl,
1—(Chlormethyl)—2—chlorethoxycarbonyl,1- (chloromethyl) -2-chloroethoxycarbonyl,
1—( Brommethyl )—2— romethoxycarbonyl , 4—Fluorbutoxycarbonyl ,1- (bromomethyl) -2- romethoxycarbonyl, 4-fluorobutoxycarbonyl,
4—Chlorbutoxycarbonyl, 4—Brombutoxycarbonyl oder 4—Iodbutoxycarbonyl;4-chlorobutoxycarbonyl, 4-bromobutoxycarbonyl or 4-iodobutoxycarbonyl;
C1-C6-Halogenalkoxycarbonyl: einen C1-C4-Halogenalkoxycarbo- nylrest wie voranstehend genannt, sowie 5-Fluorpentoxycarbonyl , 5-Chlorpentoxycarbonyl, 5-Brompentoxycarbonyl, 6-Fluorhexoxycarbonyl,C 1 -C 6 haloalkoxycarbonyl: a C 1 -C 4 haloalkoxycarbonyl radical as mentioned above, and 5-fluoropentoxycarbonyl, 5-chloropentoxycarbonyl, 5-bromopentoxycarbonyl, 6-fluorohexoxycarbonyl,
6-Chlorhexoxycarbonyl oder 6-Bromhexoxycarbonyl;6-chlorohexoxycarbonyl or 6-bromohexoxycarbonyl;
— (C1-C4—Alkyl )carbonyloxy: Acetyloxy, Ethylcarbonyloxy, Propylcarbonyloxy, 1—Methylethylcarbonyloxy, Butylcarbonyloxy, 1—Methylpropylcarbonyloxy,- (C 1 -C 4 alkyl) carbonyloxy: acetyloxy, ethylcarbonyloxy, propylcarbonyloxy, 1 — methylethylcarbonyloxy, butylcarbonyloxy, 1 — methylpropylcarbonyloxy,
2— ethylpropylcarbonyloxy oder 1, 1—Dimethylethylcarbonyloxy;2- ethylpropylcarbonyloxy or 1,1-dimethylethylcarbonyloxy;
— (C1-C4— lkylamino)carbonyl: z.B. Methylaminocarbonyl, Ethylaminocarbonyl , Propylaminocarbonyl , 1— ethylethylaminocarbonyl, Butylaminocarbonyl,- (C 1 -C 4 -alkylamino) carbonyl: for example methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl, 1-ethylethylaminocarbonyl, butylaminocarbonyl,
1—Methylpropylaminocarbonyl, 2—Methylpropylaminocarbonyl oder 1, 1—Dimethylethylaminocarbonyl;1-methylpropylaminocarbonyl, 2-methylpropylaminocarbonyl or 1,1-dimethylethylaminocarbonyl;
— (C1-C6—Alkylamino)carbonyl: (C1-C4—Alkylamino)carbonyl, wie vorstehend genannt, sowie z.B. Pentylaminocarbonyl,- (C 1 -C 6 alkylamino) carbonyl: (C 1 -C 4 alkylamino) carbonyl, as mentioned above, and for example pentylaminocarbonyl,
1-Methylbutylaminocarbonyl, 2-Methylbutylaminocarbonyl, 3-Methylbutylaminocarbon Dimethylpropylaminocarbonyl, 1-Ethylpropylaminocarbonyl , Hexylaminocarbonyl ,1-methylbutylaminocarbonyl, 2-methylbutylaminocarbonyl, 3-methylbutylaminocarbon dimethylpropylaminocarbonyl, 1-ethylpropylaminocarbonyl, hexylaminocarbonyl,
1, 1-Dimethylpropylaminocarbonyl,1, 1-dimethylpropylaminocarbonyl,
1 , 2-Dimethylpropylaminocarbonyl , 1-Methylpentylaminocarbonyl ,1, 2-dimethylpropylaminocarbonyl, 1-methylpentylaminocarbonyl,
2-Methylpentylaminocarbonyl , 3-Methylpentylaminocarbonyl , 4-Methylpentylaminocarbonyl, 1, 1-Dimethylbutylaminocarbonyl,2-methylpentylaminocarbonyl, 3-methylpentylaminocarbonyl, 4-methylpentylaminocarbonyl, 1, 1-dimethylbutylaminocarbonyl,
1 , 2-Dimethylbutylaminocarbonyl ,1, 2-dimethylbutylaminocarbonyl,
1 , 3-Dimethylbutylaminocarbonyl ,1, 3-dimethylbutylaminocarbonyl,
2, 2-Dimethylbutylaminocarbonyl,2,2-dimethylbutylaminocarbonyl,
2 , 3-Dimethylbutylaminocarbonyl , 3, 3-Dimethylbutylaminocarbonyl, 1-Ethylbutylaminocarbonyl,2, 3-dimethylbutylaminocarbonyl, 3, 3-dimethylbutylaminocarbonyl, 1-ethylbutylaminocarbonyl,
2-Ethylbutylaminocarbonyl ,2-ethylbutylaminocarbonyl,
1,1, 2-Trimethylpropylaminocarbonyl ,1,1,2-trimethylpropylaminocarbonyl,
1,2, 2-Trimethylpropylaminocarbonyl ,1,2,2-trimethylpropylaminocarbonyl,
1-Ethyl-l-methylpropylaminocarbonyl oder l-Ethyl-2-methylpropylaminocarbonyl ;1-ethyl-l-methylpropylaminocarbonyl or l-ethyl-2-methylpropylaminocarbonyl;
Di- (C1-C4-alkyl)—aminocarbonyl : z.B.Di (C 1 -C 4 alkyl) aminocarbonyl: e.g.
N, -Dimethylaminocarbonyl , N, N-Diethylaminocarbonyl ,N, -dimethylaminocarbonyl, N, N-diethylaminocarbonyl,
N,N-Di- ( 1-methylethyl ) aminocarbonyl, N,N—Dipropylaminocarbonyl, N,N-Dibutylaminocarbonyl,N, N-di- (1-methylethyl) aminocarbonyl, N, N-dipropylaminocarbonyl, N, N-dibutylaminocarbonyl,
N,N-Di-( 1-methylpropyl)—aminocarbonyl,N, N-di- (1-methylpropyl) aminocarbonyl,
N,N-Di-( 2-methylpropyl )—aminocarbonyl,N, N-di- (2-methylpropyl) aminocarbonyl,
N,N-Di-( 1, 1-dimethylethyl)—aminocarbonyl,N, N-di- (1,1-dimethylethyl) aminocarbonyl,
N-Ethyl-N-methylaminocarbonyl , N-Methyl-N-propylaminocarbonyl,N-ethyl-N-methylaminocarbonyl, N-methyl-N-propylaminocarbonyl,
N-Methyl-N- ( 1-methylethyl)—aminocarbonyl,N-methyl-N- (1-methylethyl) aminocarbonyl,
N-Butyl-N-methylaminocarbonyl,N-butyl-N-methylaminocarbonyl,
N-Methyl-N- ( 1-methylpropyl )—aminocarbonyl,N-methyl-N- (1-methylpropyl) aminocarbonyl,
N-Methyl-N- ( 2-methylpropyl )—aminocarbonyl , N- ( 1 , 1-Dimethylethyl ) -N-methylaminocarbonyl ,N-methyl-N- (2-methylpropyl) aminocarbonyl, N- (1, 1-dimethylethyl) -N-methylaminocarbonyl,
N-Ethyl-N-propylaminocarbonyl ,N-ethyl-N-propylaminocarbonyl,
N-Ethyl-N- ( 1-methylethyl )—aminocarbonyl ,N-ethyl-N- (1-methylethyl) aminocarbonyl,
N-Butyl-N-ethylaminocarbonyl,N-butyl-N-ethylaminocarbonyl,
N-Ethyl-N- ( 1-methylpropyl )—aminocarbonyl , N-Ethyl—N-(2-methylpropyl)—aminocarbonyl,N-ethyl-N- (1-methylpropyl) aminocarbonyl, N-ethyl-N- (2-methylpropyl) aminocarbonyl,
N-Ethyl-N- ( 1 , 1-dimethylethyl )—aminocarbonyl ,N-ethyl-N- (1,1-dimethylethyl) aminocarbonyl,
N- ( 1-Methylethyl ) -N-propylaminocarbonyl ,N- (1-methylethyl) -N-propylaminocarbonyl,
N-Butyl-N-propylaminocarbonyl,N-butyl-N-propylaminocarbonyl,
N- ( 1-Methylpropyl ) -N-propylaminocarbonyl , N- ( 2-Methylpropyl ) -N-propylaminocarbonyl ,N- (1-methylpropyl) -N-propylaminocarbonyl, N- (2-methylpropyl) -N-propylaminocarbonyl,
N- ( 1 , 1-Dimethylethyl ) -N-propylaminocarbonyl ,N- (1, 1-dimethylethyl) -N-propylaminocarbonyl,
N-Butyl-N—( 1-methylethyl )—aminocarbonyl ,N-butyl-N— (1-methylethyl) aminocarbonyl,
N- ( 1-Methylethyl) -N- ( 1-methylpropyl )—aminocarbonyl,N- (1-methylethyl) -N- (1-methylpropyl) aminocarbonyl,
N- ( 1-Methylethyl ) -N- ( 2-methylpropyl )—aminocarbonyl , N- ( 1 , 1-Dimethylethyl ) -N- ( 1-methylethyl )—aminocarbonyl ,N- (1-methylethyl) -N- (2-methylpropyl) aminocarbonyl, N- (1, 1-dimethylethyl) -N- (1-methylethyl) aminocarbonyl,
N-Butyl-N- ( 1-methylpropyl )—aminocarbonyl,N-butyl-N- (1-methylpropyl) aminocarbonyl,
N-Butyl—N- ( 2-methylpropy1 arbonyl , N-Butyl-N- ( 1 , 1-dimethylethyl )—aminocarbonyl ,N-butyl — N- (2-methylpropy1 arbonyl, N-butyl-N- (1,1-dimethylethyl) aminocarbonyl,
N- ( 1-Methylpropyl ) -N- ( 2-methylpropyl )—aminocarbonyl,N- (1-methylpropyl) -N- (2-methylpropyl) aminocarbonyl,
N- ( 1 , 1-Dimethylethyl ) -N- ( 1-methylpropyl )—aminocarbonyl oderN- (1, 1-dimethylethyl) -N- (1-methylpropyl) aminocarbonyl or
N-( 1, 1-Dimethylethyl )-N-( 2-methylpropyl)—aminocarbonyl;N- (1, 1-dimethylethyl) -N- (2-methylpropyl) aminocarbonyl;
Di—( C1-C6—alkyl )—aminocarbonyl :Di— (C 1 -C 6 alkyl) aminocarbonyl:
Di—(C1-C4—alkyl)—aminocarbonyl, wie voranstehend genannt, sowie z.B. N—Methyl—N—pentylaminocarbonyl,Di (C 1 -C 4 alkyl) aminocarbonyl, as mentioned above, and, for example, N-methyl-N-pentylaminocarbonyl,
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-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—Methyl—N—hexylaminocarbonyl ,N-methyl-N-hexylaminocarbonyl,
N-Methyl-N- 1 , 1-dimethylpropyl )—aminocarbonyl , N-Methyl-N- 1 , 2-dimethylpropyl )—aminocarbonyl , N-Methyl-N- 1-methylpentyl )—aminocarbonyl, N-Methyl-N- 2-methylpentyl)—aminocarbonyl, N-Methyl-N- 3-methylpentyl)—aminocarbonyl, N-Methyl-N- 4-methylpentyl)—aminocarbonyl, N-Methyl-N- 1 , 1-dimethylbutyl )—aminocarbonyl , N-Methyl-N- 1 , 2-dimethylbuty1)—aminocarbonyl, N-Methyl-N- 1 , 3-dimethylbutyl )—aminocarbonyl, N-Methyl-N- 2 , 2-dimethylbutyl )—aminocarbonyl , N-Methyl-N- 2 , 3-dimethylbutyl )—aminocarbonyl, N-Methyl-N- 3 , 3-dimethylbutyl )—aminocarbonyl , N-Methyl-N- 1-ethylbutyl )—aminocarbonyl, N-Methyl-N- 2-ethylbutyl )—aminocarbonyl , N-Methyl-N- 1,1, 2-trimethylpropyl )—aminocarbonyl , N-Methyl-N- 1,2, 2-trimethylpropyl )—aminocarbonyl , N-Methyl-N- 1-ethyl-l-methylpropyl )—aminocarbonyl , N-Methyl-N- l-ethyl-2-methylpropyl)—aminocarbonyl,N-methyl-N-1, 1-dimethylpropyl) aminocarbonyl, N-methyl-N-1,2-dimethylpropyl) aminocarbonyl, N-methyl-N-1-methylpentyl) aminocarbonyl, N-methyl-N-2 -methylpentyl) -aminocarbonyl, N-methyl-N-3-methylpentyl) -aminocarbonyl, N-methyl-N-4-methylpentyl) -aminocarbonyl, N-methyl-N-1, 1-dimethylbutyl) -aminocarbonyl, N-methyl -N- 1,2-dimethylbuty1) -aminocarbonyl, N-methyl-N-1,3-dimethylbutyl) -aminocarbonyl, N-methyl-N-2,2-dimethylbutyl) -aminocarbonyl, N-methyl-N-2, 3-dimethylbutyl) aminocarbonyl, N-methyl-N-3, 3-dimethylbutyl) aminocarbonyl, N-methyl-N-1-ethylbutyl) aminocarbonyl, N-methyl-N-2-ethylbutyl) aminocarbonyl, N- Methyl-N-1,1,2-trimethylpropyl) aminocarbonyl, N-methyl-N-1,2,2-trimethylpropyl) aminocarbonyl, N-methyl-N-1-ethyl-l-methylpropyl) aminocarbonyl, N Methyl-N-1-ethyl-2-methylpropyl) aminocarbonyl,
N—Ethyl—N—pentylaminocarbonyl,N-ethyl-N-pentylaminocarbonyl,
N-Ethyl-N- 1-methylbuty1 )—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-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—Ethyl—N—hexylaminocarbonyl,N-ethyl-N-hexylaminocarbonyl,
N-Ethyl-N- 1 , 1-dimethylpropyl )—aminocarbonyl , N-Ethyl-N- 1 , 2-dimethylpropyl )—aminocarbonyl , N-Ethyl-N- 1-methylpentyl)—aminocarbonyl, N-Ethyl-N- 2-methylpentyl )—aminocarbonyl , N-Ethyl-N- 3-methylpentyl)—aminocarbonyl, N-Ethyl-N- 4-methylpentyl)—aminocarbonyl, N-Ethyl-N- 1 , 1—dimethylbutyl )—aminocarbonyl, N-Ethyl-N- 1 , 2-dimethylb inocarbonyl, N—Ethyl—N—( 1 , 3-dimethylbutyl)—aminocarbonyl, N—Ethyl—N—( 2 , 2-dimethylbutyl)—aminocarbonyl, N—Ethyl——( 2 , 3-dimethylbutyl)—aminocarbonyl, N—Ethyl—N—( 3, 3-dimethylbutyl)—aminocarbonyl, N—Ethyl—N—( 1-ethylbutyl)—aminocarbonyl, N—Ethyl—N—( 2-ethylbuty1 )—aminocarbonyl , N—Ethyl—N—( 1,1, 2-trimethylpropyl)—aminocarbonyl, N—Ethyl—N—( 1,2, 2-trimethylpropyl )—aminocarbonyl , N—Ethyl——( 1-ethyl-l-methylpropyl)—aminocarbonyl, N—Ethyl—N—( l-ethyl-2-methylpropyl )—aminocarbonyl, N—Propyl—N—pentylaminocarbonyl,N-ethyl-N-1, 1-dimethylpropyl) aminocarbonyl, N-ethyl-N-1, 2-dimethylpropyl) aminocarbonyl, N-ethyl-N-1-methylpentyl) aminocarbonyl, N-ethyl-N-2 -methylpentyl) -aminocarbonyl, N-ethyl-N-3-methylpentyl) -aminocarbonyl, N-ethyl-N-4-methylpentyl) -aminocarbonyl, N-ethyl-N-1, 1-dimethylbutyl) -aminocarbonyl, N-ethyl -N- 1,2-dimethylb inocarbonyl, N — ethyl — N— (1,3-dimethylbutyl) aminocarbonyl, N — ethyl — N— (2,2-dimethylbutyl) aminocarbonyl, N — ethyl — (2,3-dimethylbutyl) aminocarbonyl, N-ethyl —N— (3,3-dimethylbutyl) —aminocarbonyl, N — ethyl — N— (1-ethylbutyl) —aminocarbonyl, N — ethyl — N— (2-ethylbuty1) —aminocarbonyl, N — ethyl — N— (1, 1,2-trimethylpropyl) -aminocarbonyl, N-ethyl-N— (1,2,2-trimethylpropyl) -aminocarbonyl, N-ethyl —— (1-ethyl-l-methylpropyl) -aminocarbonyl, N-ethyl-N— (l-ethyl-2-methylpropyl) aminocarbonyl, N-propyl-N-pentylaminocarbonyl,
N—Butyl—N—pentylaminocarbonyl, N,N—Dipentylaminocarbonyl, N—Propyl—N—hexylaminocarbonyl, N—Butyl—N—hexylaminocarbonyl, N—Pentyl——hexylaminocarbonyl oder N,N—Dihexylaminocarbonyl;N-butyl-N-pentylaminocarbonyl, N, N-dipentylaminocarbonyl, N-propyl-N-hexylaminocarbonyl, N-butyl-N-hexylaminocarbonyl, N-pentyl-hexylaminocarbonyl or N, N-dihexylaminocarbonyl;
Di-(C1-C6-alkyl)—aminothiocarbonyl: z.B.Di (C 1 -C 6 alkyl) aminothiocarbonyl: e.g.
N,N-Dimethylaminothiocarbonyl , N,N-Diethylaminothiocarbony1,N, N-dimethylaminothiocarbonyl, N, N-diethylaminothiocarbony1,
N, -Di- ( 1-methylethyl ) aminothiocarbonyl ,N, -Di- (1-methylethyl) aminothiocarbonyl,
N,N—Dipropylaminothiocarbonyl, ,N-Dibutylaminothiocarbony1, N,N-Di-( 1-methylpropyl)—aminothiocarbonyl, N, N-Di- ( 2-methylpropyl )—aminothiocarbonyl, N,N-Di-( 1, 1-dimethylethyl)—aminothiocarbonyl, N-Ethyl-N-methylaminothiocarbonyl, N-Methyl-N-propylaminothiocarbonyl, N-Methyl-N- ( 1-methylethyl )—aminothiocarbonyl , N-Butyl-N-methylaminothiocarbonyl, N-Methyl-N- ( 1-methylpropyl )—aminothiocarbonyl , N-Methyl-N- ( 2-methylpropyl )—aminothiocarbonyl , N- ( 1 , 1-Dimethylethyl ) -N-methylaminothiocarbonyl, N—Ethyl—N-propylaminothiocarbonyl ,N, N — Dipropylaminothiocarbonyl,, N-Dibutylaminothiocarbony1, N, N-Di- (1-methylpropyl) —aminothiocarbonyl, N, N-Di- (2-methylpropyl) —aminothiocarbonyl, N, N-Di- (1, 1- dimethylethyl) aminothiocarbonyl, N-ethyl-N-methylaminothiocarbonyl, N-methyl-N-propylaminothiocarbonyl, N-methyl-N- (1-methylethyl) -aminothiocarbonyl, N-butyl-N-methylaminothiocarbonyl, N-methyl-N- ( 1-methylpropyl) aminothiocarbonyl, N-methyl-N- (2-methylpropyl) aminothiocarbonyl, N- (1,1-dimethylethyl) -N-methylaminothiocarbonyl, N-ethyl-N-propylaminothiocarbonyl,
N-Ethyl-N- ( 1-methylethyl )—aminothiocarbonyl , N-Butyl-N-ethylaminothiocarbonyl, N-Ethyl-N- ( 1-methylpropyl )—aminothiocarbonyl , N—Ethyl—N—( 2—methylpropyl)—aminothiocarbonyl , N-Ethyl-N- ( 1, 1-dimethylethyl)—aminothiocarbonyl, N- ( 1-Methylethyl ) -N-propylaminothiocarbonyl , N-Butyl-N-propylaminothiocarbonyl, N- ( 1-Methylpropyl ) -N-propylaminothiocarbonyl , N- ( 2-Methylpropyl ) -N-propylaminothiocarbonyl , N- ( 1 , 1-Dimethylethyl ) -N-propylaminothiocarbonyl , N-Butyl-N—( 1-methylethyl )—aminothiocarbonyl , N- ( 1-Methylethyl ) -N- ( 1-methylpropyl )—aminothiocarbonyl, N- ( 1-Methylethyl ) -N- ( 2-methylpropyl )—aminothiocarbonyl , N- ( 1 , 1-Dimethylethyl ) -N- ( 1-methylethyl )-aminothiocarbonyl , N-Butyl-N-( 1-methylpropyl)—aminothiocarbonyl, N-Butyl—N-( 2-methylpropyl)—aminothiocarbonyl, N-Butyl—N- ( 1 , 1-dimethylet inothiocarbonyl, N-( 1-Methylpropyl) -N-( 2-methylpropyl )—aminothiocarbonyl , N- ( 1 , 1-Dimethylethyl ) -N- ( 1-methylpropyl )—aminothiocarbonyl , N- ( 1 , 1-Dimethylethyl ) -N- ( 2-methylpropyl )—aminothiocarbonyl , N—Methyl—N—pentylaminothiocarbonyl,N-ethyl-N- (1-methylethyl) aminothiocarbonyl, N-butyl-N-ethylaminothiocarbonyl, N-ethyl-N- (1-methylpropyl) aminothiocarbonyl, N-ethyl-N- (2-methylpropyl) aminothiocarbonyl, N-ethyl-N- (1, 1-dimethylethyl) aminothiocarbonyl, N- (1-methylethyl) -N-propylaminothiocarbonyl, N-butyl-N-propylaminothiocarbonyl, N- (1-methylpropyl) -N-propylaminothiocarbonyl, N- (2-methylpropyl) -N-propylaminothiocarbonyl, N- (1, 1-dimethylethyl) -N-propylaminothiocarbonyl, N-butyl-N- (1-methylethyl) -aminothiocarbonyl, N- (1-methylethyl) -N- (1 -methylpropyl) -aminothiocarbonyl, N- (1-methylethyl) -N- (2-methylpropyl) -aminothiocarbonyl, N- (1, 1-dimethylethyl) -N- (1-methylethyl) -aminothiocarbonyl, N-butyl-N- (1-methylpropyl) -aminothiocarbonyl, N-butyl-N- (2-methylpropyl) -aminothiocarbonyl, N-butyl-N- (1, 1-dimethylet inothiocarbonyl, N- (1-methylpropyl) -N- (2-methylpropyl) -aminothiocarbonyl, N- (1, 1-dimethylethyl) -N- (1-methylpropyl) -aminothiocarbonyl, N- (1, 1-dimethylethyl) -N- (2-methylpropyl) aminothiocarbonyl, N-methyl-N-pentylaminothiocarbonyl,
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 ,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,
N—Methyl—N—hexylaminothiocarbonyl,N-methyl-N-hexylaminothiocarbonyl,
N-Methyl-N- 1 , 1-dimethylpropy1 )—aminothiocarbonyl , N-Methyl-N- 1 , 2-dimethylpropyl)—aminothiocarbonyl, N-Methyl-N- 1-methylpentyl )—aminothiocarbonyl , N-Methyl-N- 2-methylpenty1 )—aminothiocarbonyl , N-Methyl-N- 3-methylpentyl )—aminothiocarbonyl , N-Methyl-N- 4-methylpentyl )—aminothiocarbonyl , N-Methyl-N- 1 , 1-dimethylbutyl )—aminothiocarbonyl , N-Methyl-N- 1 , 2-dimethylbutyl )—aminothiocarbonyl , N-Methyl-N- 1 , 3-dimethylbutyl )—aminothiocarbonyl , N-Methyl-N- 2 , 2-dimethylbutyl )—aminothiocarbonyl , N-Methyl-N- 2 , 3-dimethylbutyl )—aminothiocarbonyl , N-Methyl-N- 3 , 3-dimethylbutyl )—aminothiocarbonyl , N-Methyl-N- 1-ethylbutyl )—aminothiocarbonyl, N-Methyl-N- 2-ethylbutyl )—aminothiocarbonyl , N-Methyl-N→ thyl—N—( 1,1, 2-trimethylpropyl)—aminothiocarbonyl, N-Methyl-N- 1,2, 2-trimethylpropyl )—aminothiocarbonyl , N-Methyl-N- 1-ethyl-l-methylpropyl)—aminothiocarbonyl, N-Methyl-N- l-ethyl-2-methylpropyl )—aminothiocarbonyl ,N-methyl-N-1,1-dimethylpropy1) aminothiocarbonyl, N-methyl-N-1,2-dimethylpropyl) aminothiocarbonyl, N-methyl-N-1-methylpentyl) aminothiocarbonyl, N-methyl-N-2 -methylpenty1) -aminothiocarbonyl, N-methyl-N-3-methylpentyl) -aminothiocarbonyl, N-methyl-N-4-methylpentyl) -aminothiocarbonyl, N-methyl-N-1, 1-dimethylbutyl) -aminothiocarbonyl, N-methyl -N- 1,2-dimethylbutyl) aminothiocarbonyl, N-methyl-N-1,3-dimethylbutyl) aminothiocarbonyl, N-methyl-N-2,2-dimethylbutyl) aminothiocarbonyl, N-methyl-N-2, 3-dimethylbutyl) aminothiocarbonyl, N-methyl-N-3,3-dimethylbutyl) aminothiocarbonyl, N-methyl-N-1-ethylbutyl) aminothiocarbonyl, N-methyl-N-2-ethylbutyl) aminothiocarbonyl, N- Methyl-N → ethyl-N- (1,1,2-trimethylpropyl) aminothiocarbonyl, N-methyl-N-1,2,2-trimethylpropyl) aminothiocarbonyl, N-methyl-N-1-ethyl-l-methylpropyl ) —Aminothiocarbonyl, N-methyl-N-1-ethyl-2-methylpropyl) —aminothiocarbonyl,
N—Ethyl——pentylaminothiocarbonyl,N-ethyl - pentylaminothiocarbonyl,
N-Ethyl-N- 1-methylbutyl )—aminothiocarbonyl , N-Ethyl-N- 2-methylbutyl)—aminothiocarbonyl, N-Ethyl-N- 3-methylbutyl )—aminothiocarbonyl , N-Ethyl-N- 2 ,2-dimethylpropyl)—aminothiocarbonyl, N-Ethyl-N- 1-ethylpropyl )—aminothiocarbonyl,N-ethyl-N-1-methylbutyl) aminothiocarbonyl, N-ethyl-N-2-methylbutyl) aminothiocarbonyl, N-ethyl-N-3-methylbutyl) aminothiocarbonyl, N-ethyl-N-2, 2-dimethylpropyl ) —Aminothiocarbonyl, N-ethyl-N-1-ethylpropyl) —aminothiocarbonyl,
N—Ethyl—N—hexylaminothiocarbonyl,N-ethyl-N-hexylaminothiocarbonyl,
N-Ethyl-N- 1 , 1-dimethylpropyl)—aminothiocarbonyl, N-Ethyl-N- 1 , 2-dimethylpropyl )—aminothiocarbonyl , N-Ethyl-N— 1-methylpentyl)—aminothiocarbonyl, N-Ethyl-N- 2-methylpentyl )—aminothiocarbonyl , N-Ethyl-N- 3-methylpentyl)—aminothiocarbonyl, N-Ethyl-N- 4-methylpentyl )—aminothiocarbonyl , N-Ethyl-N- 1 , 1—dimethylbutyl)—aminothiocarbonyl , N-Ethyl-N- 1 , 2-dimethylbutyl )—aminothiocarbonyl , N-Ethyl-N- 1 , 3-dimethylbutyl )—aminothiocarbonyl, N-Ethyl-N- 2 , 2-dimethylbutyl )—aminothiocarbonyl , N-Ethyl-N- 2 , 3-dimethylbutyl )—aminothiocarbonyl , N-Ethyl-N- 3 , 3-dimethylb inothiocarbonyl , N—Ethyl—N—( 1-ethylbutyl )—aminothiocarbonyl, N—Ethyl—N—( 2-ethylbutyl )—aminothiocarbonyl , N—Ethyl—N—( 1,1, 2-trimethylpropyl )—aminothiocarbonyl , N—Ethyl—N—( 1, 2 , 2-trimethylpropyl )—aminothiocarbonyl, N—Ethyl—N—( 1-ethyl-l-methylpropyl )—aminothiocarbonyl, N—Ethyl—N—( l-ethyl-2-methylpropyl)—aminothiocarbonyl, N—Propyl—N—pentylaminothiocarbonyl, N—Butyl—N—pentylaminothiocarbonyl, N,N—Dipentylaminothiocarbonyl, N—Propyl—N—hexylaminothiocarbonyl , N—Butyl—N—hexylaminothiocarbonyl, N—Pentyl—N—hexylaminothiocarbonyl oder N,N—Dihexylaminothiocarbonyl;N-ethyl-N-1,1-dimethylpropyl) aminothiocarbonyl, N-ethyl-N-1,2-dimethylpropyl) aminothiocarbonyl, N-ethyl-N-1-methylpentyl) aminothiocarbonyl, N-ethyl-N-2 -methylpentyl) -aminothiocarbonyl, N-ethyl-N-3-methylpentyl) -aminothiocarbonyl, N-ethyl-N-4-methylpentyl) -aminothiocarbonyl, N-ethyl-N-1, 1-dimethylbutyl) -aminothiocarbonyl, N-ethyl -N- 1,2-dimethylbutyl) aminothiocarbonyl, N-ethyl-N-1,3-dimethylbutyl) aminothiocarbonyl, N-ethyl-N-2,2-dimethylbutyl) aminothiocarbonyl, N-ethyl-N-2, 3-dimethylbutyl) aminothiocarbonyl, N-ethyl-N-3, 3-dimethylb inothiocarbonyl, N — ethyl — N— (1-ethylbutyl) aminothiocarbonyl, N — ethyl — N— (2-ethylbutyl) aminothiocarbonyl, N — ethyl — N— (1,1, 2-trimethylpropyl) aminothiocarbonyl, N — ethyl— N— (1, 2, 2-trimethylpropyl) aminothiocarbonyl, N — ethyl — N— (1-ethyl-1-methylpropyl) aminothiocarbonyl, N — ethyl — N— (1-ethyl-2-methylpropyl) aminothiocarbonyl, N-propyl-N-pentylaminothiocarbonyl, N-butyl-N-pentylaminothiocarbonyl, N, N-dipentylaminothiocarbonyl, N-propyl-N-hexylaminothiocarbonyl, N-butyl-N-hexylaminothiocarbonyl, N-pentyl-N-hexylaminothiocarbonyl or n Dihexylaminothiocarbonyl;
C1-C6-Hydroxyalkyl: durch ein bis drei OH-Gruppen substituiertes C1-C6-Alkyl, z.B Hydroxymethyl , 1-Hydroxyethyl, 2-Hydro- xyethyl, 1, 2-Bishydroxyethyl, 1-Hydroxypropyl, 2-Hydroxypro- pyl, 3-Hydroxypropyl, 4-Hydroxybutyl, 2 , 2-Dimethyl-3-hydroxy- propyl ;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-C1-C6-alkyl: durch einen Phenylrest substituiertes C1-C6-Alkyl, z.B. Benzyl, 1-Phenylethyl und 2-Phenylethyl, wobei der Phenylrest in der angegebenen Weise teilweise oder vollständig halogeniert sein kann oder einen bis drei der für Phenyl oben angegebenen Substituenten aufweisen kann;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-C1-C6-alkyl steht dementsprechend für ein durch einen Heterocyclylrest substituiertes C1-C6-Alkyl;Heterocyclyl-C 1 -C 6 -alkyl accordingly represents a C 1 -C 6 -alkyl substituted by a heterocyclyl radical;
C1-C6-Alkoxy-C1-C6-alkyl: durch C1-C6-Alkoxy, wie vorstehend genannt, substituiertes C1-C6-Alkyl, also z.B. Methoxymethyl,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,
Ethoxymethyl, Propoxymethyl, ( l-Methylethoxy)methyl,Ethoxymethyl, propoxymethyl, (l-methylethoxy) methyl,
Butoxymethyl, ( l-Methylpropoxy)methyl,Butoxymethyl, (l-methylpropoxy) methyl,
(2-Methylpropoxy)-methyl, ( 1, 1-Dirnethylethoxy)methyl,(2-methylpropoxy) methyl, (1, 1-dimethylethoxy) methyl,
2-(Methoxy)ethyl, 2-(Ethoxy)ethyl, 2-(Propoxy)ethyl, 2-(l-Methylethoxy)ethyl, 2-(Butoxy)ethyl,2- (methoxy) ethyl, 2- (ethoxy) ethyl, 2- (propoxy) ethyl, 2- (l-methylethoxy) ethyl, 2- (butoxy) ethyl,
2-( 1-Methylpropoxy)ethyl, 2-( 2-Methylpropoxy) ethyl,2- (1-methylpropoxy) ethyl, 2- (2-methylpropoxy) ethyl,
2-( 1, 1-Dimethylethoxy)ethyl, 2- (Methoxy) -propyl,2- (1, 1-dimethylethoxy) ethyl, 2- (methoxy) propyl,
2- (Ethoxy)propyl , 2- ( Propoxy) propyl ,2- (ethoxy) propyl, 2- (propoxy) propyl,
2-( 1-Methylethoxy)—propyl, 2- (Butoxy)propyl, 2- ( 1-Methylpropoxy)propyl, 2- (2-Methylpropoxy)propyl,2- (1-methylethoxy) propyl, 2- (butoxy) propyl, 2- (1-methylpropoxy) propyl, 2- (2-methylpropoxy) propyl,
2-( 1, 1-Dimethylethoxy) ropyl, 3- (Methoxy)propyl,2- (1, 1-dimethylethoxy) ropyl, 3- (methoxy) propyl,
3- (Ethoxy)—propyl, 3- (Propoxy)propyl ,3- (ethoxy) propyl, 3- (propoxy) propyl,
3-( 1-Methylethoxy)propyl, 3-(Butoxy)propyl,3- (1-methylethoxy) propyl, 3- (butoxy) propyl,
3-( 1-Methylpropoxy)propyl, 3-( 2-Methylpropoxy)propyl, 3- ( 1, 1-Dimethylethoxy) propyl, 2- (Methoxy)butyl,3- (1-methylpropoxy) propyl, 3- (2-methylpropoxy) propyl, 3- (1, 1-dimethylethoxy) propyl, 2- (methoxy) butyl,
2-(Ethoxy)butyl, 2-(Prop—oxy)butyl, 2-( 1-Methylethoxy) utyl,2- (ethoxy) butyl, 2- (propoxy) butyl, 2- (1-methylethoxy) utyl,
2- ( Butoxy)butyl , 2-( 1-Me oxy)butyl , ( 2-Methylpropoxy)butyl, 2-( 1 , 1-Dimethylethoxy ) utyl, (Methoxy) butyl, 3- (Ethoxy) butyl, 3- (Propoxy) butyl, ( 1-Methylethoxy) butyl, 3- (Butoxy)—butyl, ( 1-Methylpropoxy ) utyl, 3-( 2-Methylpropoxy) butyl, ( 1 , 1-Dimethylethoxy) butyl, 4- (Methoxy) butyl, (Ethoxy)—butyl, 4- (Propoxy) butyl, 4- ( 1-Methylethoxy ) butyl, (Butoxy)—butyl, 4-( 1-Methylpropoxy)butyl, ( 2-Methylpropoxy)butyl oder 4-( 1, 1-Dimethylethoxy) butyl;2- (butoxy) butyl, 2- (1-Me oxy) butyl, (2-methylpropoxy) butyl, 2- (1, 1-dimethylethoxy) utyl, (methoxy) butyl, 3- (ethoxy) butyl, 3- (propoxy) butyl, (1-methylethoxy) butyl, 3- (butoxy) - butyl, (1-methylpropoxy) utyl, 3- (2-methylpropoxy) butyl, (1, 1-dimethylethoxy) butyl, 4- (methoxy) butyl, (ethoxy) butyl, 4- (propoxy) butyl, 4- ( 1-methylethoxy) butyl, (butoxy) butyl, 4- (1-methylpropoxy) butyl, (2-methylpropoxy) butyl or 4- (1, 1-dimethylethoxy) butyl;
C1-C6-Alkoxy-C1-C6-alkoxy, sowie die Alkoxyalkoxyteile von C1-C6—Alkoxy-C1-C6—alkoxycarbonyl : durch C1-C6-Alkoxy, wie vorstehend genannt, substituiertes C1-C6-Alkoxy, also z.B. fürC 1 -C 6 alkoxy-C 1 -C 6 alkoxy, and the alkoxyalkoxy parts of C 1 -C 6 alkoxy-C 1 -C 6 alkoxycarbonyl: substituted by C 1 -C 6 alkoxy, as mentioned above C 1 -C 6 alkoxy, for example for
Methoxymethoxy, Ethoxymethoxy, Propoxymethoxy,Methoxymethoxy, ethoxymethoxy, propoxymethoxy,
( 1—Methylethoxy)methoxy, Butoxymethoxy,(1-methylethoxy) methoxy, butoxymethoxy,
( 1—Methylpropoxy)methoxy, ( 2—Methylpropoxy)methoxy,(1-methylpropoxy) methoxy, (2-methylpropoxy) methoxy,
( 1 , 1—Dimethylethoxy)methoxy, 2- (Methoxy) ethoxy,(1,1-dimethylethoxy) methoxy, 2- (methoxy) ethoxy,
2- Ethoxy)ethoxy, 2- (Propoxy) ethoxy, 2- 1-Methylethoxy) ethoxy, 2- ( Butoxy) ethoxy, 2- 1-Methylpropoxy) ethoxy, 2-( 2-Methylpropoxy)ethoxy, 2- 1, 1-Dimethylethoxy) ethoxy, 2- (Methoxy) propoxy, 2- Ethoxy)propoxy, 2- ( ropoxy)propoxy, 2- 1-Methylethoxy) propoxy, 2- (Butoxy)—propoxy, 2- 1-Methylpropoxy)propoxy, 2-( 2-Methylpropoxy)propoxy, 2- 1 , 1-Dimethylethoxy) propoxy, 3- (Methoxy)—propoxy, 3- Ethoxy)propoxy, 3- ( Propoxy)propoxy, 3- 1-Methylethoxy) propoxy, 3- ( Butoxy) propoxy, 3- 1-Methylpropoxy)—propoxy, 3- ( 2-Methylpropoxy) propoxy, 3- 1 , 1-Dimethylethoxy) propoxy, 2- (Methoxy) butoxy, 2- Ethoxy)butoxy, 2- ( Propoxy)butoxy, 2- 1-Methylethoxy) butoxy, 2- (Butoxy)—butoxy, 2- 1-Methylpropoxy) butoxy, 2-( 2-Methylpropoxy) butoxy, 2- 1, 1-Dimethylethoxy) utoxy, 3- (Methoxy) butoxy, 3- Ethox )—butoxy, 3- ( Propoxy) butoxy, 3- 1-Methylethoxy) butoxy, 3- ( Butoxy) butoxy, 3- 1-Methylpropoxy) butoxy, 3- ( 2-Methylpropoxy) butoxy, 3- 1, 1-Dimethylethoxy) butoxy, 4- (Methoxy)—butoxy, 4- Ethoxy)butoxy, 4- ( Propoxy) butoxy, 4- 1-Methylethoxy) butoxy, 4- ( Butoxy) butoxy, 4- 1-Methylpropoxy) butoxy, 4- ( 2-Methylpropoxy) butoxy oder 4- 1 , 1-Dimethylethoxy) butoxy;2- ethoxy) ethoxy, 2- (propoxy) ethoxy, 2- 1-methylethoxy) ethoxy, 2- (butoxy) ethoxy, 2- 1-methylpropoxy) ethoxy, 2- (2-methylpropoxy) ethoxy, 2- 1, 1 -Dimethylethoxy) ethoxy, 2- (methoxy) propoxy, 2-ethoxy) propoxy, 2- (ropoxy) propoxy, 2- 1-methylethoxy) propoxy, 2- (butoxy) propoxy, 2- 1-methylpropoxy) propoxy, 2 - (2-methylpropoxy) propoxy, 2- 1, 1-dimethylethoxy) propoxy, 3- (methoxy) propoxy, 3-ethoxy) propoxy, 3- (propoxy) propoxy, 3- 1-methylethoxy) propoxy, 3- ( Butoxy) propoxy, 3- 1-methylpropoxy) —propoxy, 3- (2-methylpropoxy) propoxy, 3- 1, 1-dimethylethoxy) propoxy, 2- (methoxy) butoxy, 2-ethoxy) butoxy, 2- (propoxy) butoxy, 2- 1-methylethoxy) butoxy, 2- (butoxy) —butoxy, 2- 1-methylpropoxy) butoxy, 2- (2-methylpropoxy) butoxy, 2- 1, 1-dimethylethoxy) utoxy, 3- (methoxy) butoxy, 3-ethox) —butoxy, 3- (propoxy) butoxy, 3- 1-methylethoxy) butoxy, 3- (butoxy) butoxy, 3- 1-methylpropoxy) butoxy, 3- (2-methylpropoxy) butoxy, 3- 1, 1-dimethylethoxy) butoxy, 4- (methoxy ) —Butoxy, 4-ethoxy) butoxy, 4- (propoxy) butoxy, 4- 1-methylethoxy) butoxy, 4- (butoxy) butoxy, 4- 1-methylpropoxy) butoxy, 4- (2-methylpropoxy) butoxy or 4 - 1, 1-dimethylethoxy) butoxy;
C1-C6-Alkylcarbonyl-C1-C6-alkyl: Durch eine C1-C6-Alkylcarbonylgruppe substituiertes C1-C6-Alkyl, worin beide der C1-C6-Alkylgruppen ein oder mehrere Substituenten, ausgewählt unter C1-C4-Alkoxy und/oder Hydroxy aufweisen können: z.B. Acetylmethyl (=2-0xopropyl) , 2-(Acetyl)ethyl (=3-Oxo-n-butyl) , 3-0xo-n-pentyl, 1, l-Dimethyl-2-oxopropyl, 3-Hydroxy-2-oxopropyl oder 3-Hydroxy-2-oxobutyl .C 1 -C 6 alkylcarbonyl-C 1 -C 6 alkyl: C 1 -C 6 alkyl substituted by a C 1 -C 6 alkylcarbonyl group, wherein both of the C 1 -C 6 alkyl groups have one or more substituents selected may have C 1 -C 4 alkoxy and / or hydroxy: for example acetylmethyl (= 2-0xopropyl), 2- (acetyl) ethyl (= 3-oxo-n-butyl), 3-0xo-n-pentyl, 1, l-dimethyl-2-oxopropyl, 3-hydroxy-2-oxopropyl or 3-hydroxy-2-oxobutyl.
C3—C6—Alkenyl , sowie die Alkenylteile von C3—C6—Alkenylcarbonyl, C3-C6-Alkenyloxy,C 3 -C 6 alkenyl, and the alkenyl parts of C 3 -C 6 alkenylcarbonyl, C 3 -C 6 alkenyloxy,
C3—C6—Alkenyloxycarbonyl, C3-C6—Alkenylaminocarbonyl , N—(C3-C6-Alkenyl)—N-(C1-C6-alkyl) aminocarbonyl, N—(C3—C6—Alkenyl)—N—(C1-C6—alkoxy) aminocarbonyl : z.B. Prop—2—en—1—yl, But—1—en—4—yl , 1—Methyl—prop—2—en—1—yl, 2—Methyl—prop—2-en—1—yl , 2-Buten—1—yl , 1-Penten—3—yl , 1—Penten—4—yl, 2—Penten—4—yl, 1—Methyl—but—2—en—1—yl , 2-Methyl-but-2-en-l-y1 , 3-Methy1-but—2-en-l-y1, l-Methyl-but-3-en-l-yl , 2-Methyl-but-3-en-l-yl , 3—Methyl—but—3—en—1—yl , 1 , 1—Dimethy1—prop—2—en—1—yl , 1, 2—Dimethy1—prop—2—en—1—yl, 1—Ethyl—prop—2—en—1—yl, Hex—3—en—1—yl , Hex—4—en—1—yl, Hex—5—en—1—yl , 1—Methy1—pent—3—en—1—yl, 2—Methyl—pent—3—en—1—yl , 3—Methy1—pent—3—en—1—yl, 4—Methyl—pent—3—en—1—yl , 1—Methyl—pent—4—en—1—yl, 2—Methyl—pent—4—en—1—yl , 3—Methyl—pent—4—en—1—yl , 4—Methyl—pent—4—en—1—yl ,C 3 -C 6 alkenyloxycarbonyl, C 3 -C 6 alkenylaminocarbonyl, N - (C 3 -C 6 alkenyl) -N- (C 1 -C 6 alkyl) aminocarbonyl, N - (C 3 -C 6 - Alkenyl) —N— (C 1 -C 6 alkoxy) aminocarbonyl: for example prop-2-ene-1-yl, but-1-ene-4-yl, 1-methyl-prop-2-ene-1-yl , 2-methyl-prop-2-ene-1-yl, 2-butene-1-yl, 1-pentene-3-yl, 1-pentene-4-yl, 2-pentene-4-yl, 1-methyl -But-2-en-1-yl, 2-methyl-but-2-en-l-y1, 3-methyl-but-2-en-l-y1, l-methyl-but-3-en-l -yl, 2-methyl-but-3-en-1-yl, 3-methyl-but-3-en-1-yl, 1, 1-dimethyl-prop-2-ene-1-yl, 1, 2 —Dimethy1-prop-2-en-1-yl, 1-ethyl-prop-2-en-1-yl, hex-3-en-1-yl, hex-4-en-1-yl, hex-5 -En-1-yl, 1-methyl-pent-3-en-1-yl, 2-methyl-pent-3-en-1-yl, 3-methyl-1-pent-3-en-1-yl, 4 - methyl-pent-3-ene-1-yl, 1-methyl-pent-4-ene-1-yl, 2-methyl-pent-4-ene-1-yl, 3 - methyl-pent-4-ene-1-yl, 4-methyl-pent-4-ene-1-yl,
1 , 1—Dimethy1—but—2—en—1—yl, 1 , 1—Dimethy1—but—3—en—1—yl , 1 , 2—Dimethy1—but—2-en—1—yl, 1 , 2—Dimethy1—but—3—en—1—yl, 1 , 3—Dimethy1—but—2—en—1—yl , 1 , 3—Dimethy1—but—3—en—1—yl , 2 , 2-Dimethyl-but-3-en-l-yl , 2 , 3-Dimethyl-but-2-en-l-yl, 2,3-Dimethyl-but-3-en-l-yl, 3 , 3-Dimethyl-but-2-en-l-yl, l-Ethyl-but-2-en-l-y1, 1-Ethyl-but-3-en-l-yl, 2-Ethyl-but-2-en-l-y1, 2-Ethyl-but-3-en-l-yl , 1,1, 2—Trimethyl—prop—2-en—1—yl , 1—Ethyl—1—methy1—prop—2—en—1—yl oder l-Ethyl-2-methyl-prop-2-en-l-yl ;1, 1-Dimethy1-but-2-en-1-yl, 1, 1-Dimethy1-but-3-en-1-yl, 1, 2-Dimethy1-but-2-en-1-yl, 1, 2 — Dimethy1 — but — 3 — en — 1 — yl, 1, 3 — Dimethy1 — but — 2 — en — 1 — yl, 1, 3 — Dimethy1 — but — 3 — en — 1 — yl, 2, 2- Dimethyl-but-3-en-l-yl, 2, 3-dimethyl-but-2-en-l-yl, 2,3-dimethyl-but-3-en-l-yl, 3, 3-dimethyl but-2-en-l-yl, l-ethyl-but-2-en-l-y1, 1-ethyl-but-3-en-l-yl, 2-ethyl-but-2-en-l- y1, 2-ethyl-but-3-en-l-yl, 1,1, 2-trimethyl-prop-2-ene-1-yl, 1-ethyl-1-methyl-1-prop-2-ene-1 - yl or l-ethyl-2-methyl-prop-2-en-l-yl;
C2—C6—Alkenyl, sowie die Alkenylteile von C2-C6—Alkenylcarbonyl, Phenyl—C2-C6—alkenylcarbonyl und Heterocyclyl—C2—C6—alkenylcarbonyl : C3—C6—Alkenyl, wie voranstehend genannt, sowie Ethenyl;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;
— C3—C6—Halogenalkenyl: einen C3—C6—Alkenylrest, wie vorstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder Iod substituiert ist, also z.B. 2—Chlorallyl, 3-Chlorallyl, 2,3-Dichlorallyl, 3 , 3-Dichlorallyl,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,
2,3,3-Tri-chlorallyl, 2, 3-Dichlorbut-2-enyl, 2-Bromallyl, 3—Bromallyl, 2 , 3—Dibromallyl, 3 , 3—Dibromallyl, 2, 3 , 3—Tribromallyl oder 2 , 3—Dibrombut—2—enyl;2,3,3-trichloroallyl, 2, 3-dichlorobut-2-enyl, 2-bromoallyl, 3-bromoallyl, 2, 3-dibromoallyl, 3, 3-dibromoallyl, 2, 3, 3-tribromoallyl or 2, 3-dibromobut-2-enyl;
— C3—C6—Alkinyl, sowie die Alkinylteile von- C 3 -C 6 alkynyl, and the alkynyl parts of
C3—C6—Alkinylcarbonyl, C3-C6-Alkinyloxy, C3—C6—Alkinyloxycar- bonyl, C3—C6—Alkinylamino , N—(C3-C6-Alkinyl)—N—(C1-C6—alkyl)—aminocarbonyl, N—(C3—C6—Alkinyl)—N—(C1-C6—alkoxy) aminocarbonyl : z.B. Propargyl, But—1—in—3—yl , But—1—in—4—yl, But—2—in—1—yl, Pent—1—in—3—yl, Pent—1—in—4—yl, Pent—1—in—5—yl, Pent—2—in—1—yl, Pent—2—in—4—yl, Pent—2—in—5—yl, 3-Methy1-but-l-in—3-y1, 3-Methyl-but-l-in-4-y1, Hex—1—in—3—yl , Hex—1—in—4—yl, Hex—1—in—5—yl, Hex—1—in—6—yl , Hex-2-in-l-yl , Hex-2-in-4-yl , Hex-2-in-5-yl , Hex-2-in-6-yl , Hex—3—in—1—yl , Hex—3—in—2—yl , 3—Methyl— ent—1—in—3—yl , 3—Methyl—pent—1—in—4—yl , 3—Methyl—pent—1—in—5—yl ,C 3 -C 6 alkynylcarbonyl, C 3 -C 6 alkynyloxy, C 3 -C 6 alkynyloxycarbonyl, C 3 -C 6 alkynylamino, N- (C 3 -C 6 alkynyl) —N— (C 1 -C 6 alkyl) aminocarbonyl, N— (C 3 -C 6 alkynyl) —N— (C 1 -C 6 alkoxy) aminocarbonyl : eg propargyl, but — 1 in 3 yl, but 1 in 4 yl, but 2 in 1 in yl, pent 1 in 3 yl, pent 1 in 4-yl, pent-1-in-5-yl, pent-2-in-1-yl, pent-2-in-4-yl, pent-2-in-5-yl, 3-methyl-1-but- l-in-3-y1, 3-methyl-but-l-in-4-y1, hex-1-in-3-yl, hex-1-in-4-yl, hex-1-in-5- yl, hex — 1-in-6-yl, hex-2-in-1-yl, hex-2-in-4-yl, hex-2-in-5-yl, hex-2-in-6- yl, hex — 3-in-1-yl, hex-3-in-2-yl, 3-methyl-ent-1-in-3-yl, 3-methyl-pent-1-in-4-yl, 3-methyl-pent-1-in-5-yl,
4—Methyl—pent—2—in—4—yl oder 4—Methyl—pent—2—in—5—yl ;4-methyl-pent-2-in-4-yl or 4-methyl-pent-2-in-5-yl;
— C2—C6—Alkinyl, sowie die Alkinylteile von- C 2 -C 6 alkynyl, and the alkynyl parts of
C—C6—Alkinylcarbonyl: C3—C6—Alkinyl, wie voranstehend genannt, sowie Ethinyl;C -C 6 alkynylcarbonyl: C 3 -C 6 alkynyl as mentioned above and ethynyl;
— C3—C6—Halogenalkinyl: einen C3-C6—Alkinylrest, wie vorstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder Iod substituiert ist, also z.B. 1, 1—Difluor—prop—2—in—1—yl, 3—Iod—prop—2-in—1—yl, 4-Fluorbut-2-in-l-yl , 4-Chlorbut-2-in-l-yl , 1 , 1—Difluorbut—2—in—1—yl , 4—Iod—but—3—in—1—yl , 5—Fluorpent—3—in—1—yl , 5—Iod—pent—4—in—1-yl, 6—Fluor—hex—4—in—1—yl oder 6—Iod—hex—5—in—1—yl;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;
C1-C6-Alkandiyl: Methandiyl, Ethan-1, 1-diyl, Ethan-1, 2-diyl, Propan-1, 1-diyl, Propan-1, 2-diyl, Propan-l,3-diyl, Propan-2, -diyl, Butan-1, 1-diyl, Butan-1, 2-diyl, Butan-l,3-diyl, Butan-1, 4-diyl, 2-Methyl-propan-l, 3-diyl, 2-Methyl-propan-l, 2-diyl, 2-Methyl-propan-l, 1-diyl, 1-Methyl-propan-l , 2-diyl, l-Methyl-propan-2 , 2-diyl, 1-Methyl-propan-l, 1-diyl, Pentan-1 , 1-diyl, Pentan-1, 2-diyl, Pentan-1, 3-diyl, Pentan-l,5-diyl, Pentan-2, 3-diyl, Pentan-2, 2-diyl, 1-Methyl-butan-l, 1-diyl, 1-Methyl-butan-l, 2-diyl, 1-Methyl-butan-l, 3-diyl, 1-Methyl-butan-l, 4-diyl, 2-Methyl-butan-l, 1-diyl, 2-Methyl-butan-l, 2-diyl, 2-Methyl-butan-l, 3-diyl, 2-Methyl-butan-l, 4-diyl, 2, 2-Dimethy1-propan-l, 1-diyl, 2,2-Dimethyl-propan-l , 3-diyl, 1, 1-Dimethyl-propan-l, 3-diyl, 1, 1-Dimethyl-propan-l, 2-diyl, 2 , 3-Dimethyl-propan-l , 3-diyl, 2, 3-Dimethy1-propan-l, 2-diyl, 1 ,3-Dimethyl-propan-l, 3-diyl, Hexan-1, 1-diyl, Hexan-1, 2-diyl, Hexan-1, 3-diyl, Hexan-1 , 4-diyl-, Hexan-1, 5-diyl, Hexan-l,6-diyl, Hexan-2 , 5-diyl, 1-Methyl-pentan-l , 1-diyl, 1-Methyl-pentan-l, 2-diyl, 1-Methyl-pentan-l, 3-diyl, 1-Methyl-pentan-l, 4-diyl, 1-Methyl-pentan-l, 5-diyl, 2-Methyl-pentan-l, 1-diyl hyl-pentan-l, 2-diyl, 2-Methyl-pentan-l, 3-diyl, 2-Methyl-pentan-l, 4-diyl, 2-Methyl-pentan-l, 5-diyl, 3-Methyl-pentan-l, 1-diyl, 3-Methyl-pentan-l , 2-diyl, 3-Methyl-pentan-l , 3-diyl, 3-Methyl-pentan-l , 4-diyl, 3-Methyl-pentan-l , 5-diyl, 1, 1-Dimethyl-butan-l, 2-diyl, 1, 1-Dimethyl-butan-l , 3-diyl, 1, 1-Dimethy1-butan-1, 4-diyl, 1, 2-Dimethyl-butan-l , 1-diyl, 1, 2-Dimethyl-butan-l, 2-diyl, 1, 2-Dimethyl-butan-l , 3-diyl, 1, 2-Dimethyl-butan-l, 4-diyl, 1 , 3-Dimethyl-butan-l, 1-diyl, 1, 3-Dimethyl-butan-l , 2-diyl, 1 , 3-Dimethyl-butan-l , 3-diyl, 1,3-Dimethyl-butan-l, 4-diyl, 1-Ethyl-butan-l, 1-diyl, 1-Ethyl-butan-l , 2-diyl, 1-Ethyl-butan-l , 3-diyl, 1-Ethyl-butan-l, 4-diyl, 2-Ethyl-butan-l , 1-diyl, 2-Ethyl-butan-l, 2-diyl, 2-Ethyl-butan-l, 3-diyl, 2-Ethyl-butan-l, 4-diyl, 2-Ethyl-butan-2 , 3-diyl, 2, 2-Dimethyl-butan-l, 1-diyl, 2 , 2-Dimethyl-butan-l , 3-diyl, 2 , 2-Dimethy1-butan—1, 4-diyl, 1-Isopropyl-propan-l, 1-diyl, 1-Isopropyl-propan-l, 2-diyl, 1-Isopropyl-propan-l, 3-diyl, 2-Isopropyl-propan-l , 1-diyl , 2-Isopropyl-propan-l , 2-diyl , 2-Isopropyl-propan-l, 3-diyl, 1,2, 3-Trimethyl-propan-l, 1-diyl, 1, 2 , 3-Trimethyl-propan-l, 2-diyl oder 1,2, 3-Trimethyl-propan-l, 3-diyl;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, pentane-1, 3-diyl, pentane-l, 5-diyl, pentane-2, 3-diyl , Pentane-2, 2-diyl, 1-methyl-butane-1, 1-diyl, 1-methyl-butane-1, 2-diyl, 1-methyl-butane-1, 3-diyl, 1-methyl-butane -l, 4-diyl, 2-methyl-butane-l, 1-diyl, 2-methyl-butane-l, 2-diyl, 2-methyl-butane-l, 3-diyl, 2-methyl-butane-l , 4-diyl, 2, 2-dimethy1-propane-l, 1-diyl, 2,2-dimethyl-propane-l, 3-diyl, 1, 1-dimethyl-propane-l, 3-diyl, 1, 1 -Dimethyl-propane-1,2-diyl, 2,3-dimethyl-propane-1,3-diyl, 2,3-dimethyl-propane-1,2-diyl, 1,3-dimethyl-propane-1,3 -diyl, hexane-1, 1-diyl, hexane-1, 2-diyl, hexane-1, 3-diyl, hexane-1, 4-diyl, hexane-1, 5-diyl, hex an-l, 6-diyl, hexane-2, 5-diyl, 1-methyl-pentane-l, 1-diyl, 1-methyl-pentane-l, 2-diyl, 1-methyl-pentane-l, 3- diyl, 1-methyl-pentane-l, 4-diyl, 1-methyl-pentane-l, 5-diyl, 2-methyl-pentane-l, 1-diyl-hyl-pentane-l, 2-diyl, 2-methyl-pentane-l, 3-diyl, 2-methyl-pentane-l, 4-diyl, 2-methyl-pentane-l, 5-diyl, 3-methyl-pentane-l, 1-diyl, 3- Methyl-pentane-l, 2-diyl, 3-methyl-pentane-l, 3-diyl, 3-methyl-pentane-l, 4-diyl, 3-methyl-pentane-l, 5-diyl, 1, 1- Dimethyl-butane-1,2-diyl, 1,1-dimethyl-butane-1,3-diyl, 1,1-dimethyl-butane-1,4-diyl, 1,2-dimethyl-butane-1,1 diyl, 1,2-dimethyl-butane-1,2-diyl, 1,2-dimethyl-butane-1,3-diyl, 1,2-dimethyl-butane-1,4-diyl, 1,3-dimethyl butane-l, 1-diyl, 1, 3-dimethyl-butane-l, 2-diyl, 1, 3-dimethyl-butane-l, 3-diyl, 1,3-dimethyl-butane-l, 4-diyl, 1-ethyl-butane-l, 1-diyl, 1-ethyl-butane-l, 2-diyl, 1-ethyl-butane-l, 3-diyl, 1-ethyl-butane-l, 4-diyl, 2- Ethyl-butane-l, 1-diyl, 2-ethyl-butane-l, 2-diyl, 2-ethyl-butane-l, 3-diyl, 2-ethyl-butane-l, 4-diyl, 2-ethyl- butane-2,3-diyl, 2,2-dimethyl-butane-1,1-diyl, 2,2-dimethyl-butane-1,3-diyl, 2,2-dimethyl-butane-1,4-diyl, 1-isopropyl-propane-l, 1-diyl, 1-isopropyl-propane-l, 2-diyl, 1-isopropyl-propane-l, 3-diyl, 2-isopropyl-prop an-l, 1-diyl, 2-isopropyl-propane-l, 2-diyl, 2-isopropyl-propane-l, 3-diyl, 1,2, 3-trimethyl-propane-l, 1-diyl, 1, 2,3-trimethyl-propane-1,2-diyl or 1,2,3-trimethyl-propane-1,3-diyl;
— C3—C6—Cycloalkyl, sowie die Cycloalkylteile von C3-C6-Cycloalkylamino und C3-C6-Cycloalkylcarbonyl: z.B. Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl;- 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, sowie Heterocyclylteile von Heterocyclyloxy, Heterocyclylcarbonyl , Heterocyclyl—C1—C4—alkyl, Heterocyclyl-C1-C6-alkyl, Heterocyclylsulfonyl oder Heterocyclyloxysulfonyl, Heterocyclyloxycarbonyl, Heterocyclyloxythiocarbonyl , Heterocyclyl-C2-C6-alkenylcarbonyl, Heterocyclylcarbonyl—C1-C6—alkyl , N—( C1-C6— lkyl )—N—( heterocyclyl )—aminocarbonyl , Heterocyclylaminocarbonyl: ein gesättigter, partiell gesättigter oder ungesättigter 5— oder 6— liedriger, heterocyclischer Ring, der ein, zwei, drei oder vier gleiche oder verschiedene Heteroatome, ausgewählt aus folgender Gruppe: Sauerstoff, Schwefel oder Stickstoff, enthält, also z.B. C-gebundene 5—gliedrige Ringe wie:- heterocyclyl, and Heterocyclylteile 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:
Tetrahydrofuran—2—yl , Tetrahydrofuran—3—yl , Tetrahydrothien—2—yl , Tetrahydrothien—3—yl , Tetrahydropyrrol—2—yl , Tetrahydropyrrol—3—yl , 2 , 3—Dihydrofuran—2—yl , 2 , 3—Dihydrofuran—3—yl, 2 , 5—Dihydrofuran—2—yl , 2 , 5—Dihydrofuran-3—yl, 4 , 5—Dihydrofuran—2—yl, drofuran—3—yl, 2 , 3—Dihydrothien—2—yl , 2 , 3—Dihydrothien—3—yl , 2 , 5—Dihydrothien—2—yl, 2 , 5—Dihydrothien—3—yl, 4 , 5—Dihydrothien—2—yl , 4 , 5—Dihydrothien—3—yl ,Tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydrothiene-2-yl, tetrahydrothiene-3-yl, tetrahydropyrrole-2-yl, tetrahydropyrrole-3-yl, 2,3-dihydrofuran-2-yl, 2,3- Dihydrofuran-3-yl, 2.5-dihydrofuran-2-yl, 2.5-dihydrofuran-3-yl, 4.5-dihydrofuran-2-yl, drofuran-3-yl, 2,3-dihydrothiene-2-yl, 2,3-dihydrothiene-3-yl, 2,5-dihydrothiene-2-yl, 2,5-dihydrothiene-3-yl, 4,5-dihydrothiene-2-yl, 4,5-dihydrothien-3-yl,
2 , 3-Dihydro-lH-pyrrol-2-yl , 2 , 3-Dihydrc—lH-pyrrol-3-yl, 2 , 5-Dihydro-lH-pyrrol-2-yl , 2 , 5-Dihydro-lH-pyrrol-3-yl ,2,3-dihydro-lH-pyrrol-2-yl, 2,3-dihydrc-lH-pyrrol-3-yl, 2,5-dihydro-lH-pyrrol-2-yl, 2,5-dihydro-lH- pyrrol-3-yl,
4 , 5—Dihydro—1H—pyrrol—2—yl, 4 , 5—Dihydro—1H—pyrrol—3—yl, 3 , 4-Dihydro-2H-pyrrol-2-yl , 3 , 4-Dihydro-2H-pyrrol-3-yl,4,5-dihydro-1H-pyrrole-2-yl, 4,5-dihydro-1H-pyrrole-3-yl, 3,4-dihydro-2H-pyrrol-2-yl, 3,4-dihydro-2H- pyrrol-3-yl,
3 , 4—Dihydro—5H—pyrrol—2—yl, 3 , 4—Dihydro—5H—pyrrol—3—yl, 2—Furyl, 3—Furyl, 2—Thienyl, 3—Thienyl, Pyrrol—2—yl, Pyrrol—3—yl, Tetrahydropyrazol—3—yl, Tetrahydropyrazol—4—yl, Tetrahydroisoxazol—3—yl , Tetrahydroisoxazol—4—yl , Tetrahydroisoxazol—5—yl, 1 , 2—Oxathiolan—3—yl, 1 , 2-Oxathiolan—4—yl , 1 , 2—Oxathiolan—5—yl , Tetrahydroisothiazol—3—yl , Tetrahydro-isothiazol—4—yl, Tetrahydroisothiazol—5—yl, 1, 2—Dithiolan—3—yl, 1 , 2—Dithiolan—4—yl , Tetrahydroimidazol—2—yl , Tetrahydroimidazol—4—yl , Tetrahydrooxazol—2—yl , Tetrahydrooxazol—4—yl , Tetrahydrooxazol—5—yl , Tetrahydrothiazol—2—yl , Tetrahydrothiazol—4—yl , Tetrahydrothiazol—5—yl, 1, 3—Dioxolan—2—yl,3,4-dihydro-5H-pyrrole-2-yl, 3,4-dihydro-5H-pyrrole-3-yl, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, pyrrole-2-yl, Pyrrole-3-yl, tetrahydropyrazole-3-yl, tetrahydropyrazole-4-yl, tetrahydroisoxazole-3-yl, tetrahydroisoxazole-4-yl, tetrahydroisoxazole-5-yl, 1,2-oxathiolane-2-yl, 1,1 Oxathiolane-4-yl, 1,2-oxathiolan-5-yl, tetrahydroisothiazole-3-yl, tetrahydro-isothiazole-4-yl, tetrahydroisothiazole-5-yl, 1,2-dithiolane-3-yl, 1,2- Dithiolan-4-yl, tetrahydroimidazole-2-yl, tetrahydroimidazole-4-yl, tetrahydrooxazole-2-yl, tetrahydrooxazole-4-yl, tetrahydrooxazole-5-yl, tetrahydrothiazol-2-yl, tetrahydrothiazole-2-yl, 5-yl, 1, 3-dioxolane-2-yl,
1 , 3—Dioxolan—4—yl , 1, 3-Oxathiolan—2—yl, 1, 3-Oxathiolan—4—yl, 1 , 3-Oxathiolan-5-yl , 1 , 3-Dithiolan-2-yl , 1, 3-Dithiolan-4-yl,1,3-dioxolane-4-yl, 1,3-oxathiolane-2-yl, 1,3-oxathiolane-4-yl, 1,3-oxathiolan-5-yl, 1,3-dithiolan-2-yl, 1, 3-dithiolan-4-yl,
4 , 5-Dihydro-lH-pyrazol-3-yl, 4 , 5-Dihydro-lH-pyrazol-4-yl, 4 , 5—Dihydro-IH—pyrazol-5— l , 2 , 5-Dihydro-lH—pyrazol—3—yl , 2,5-Dihydro-lH-pyrazol-4-yl, 2 , 5-Dihydro-lH-pyrazol-5-yl, 4 , 5—Dihydroisoxazol—3—yl , 4 , 5—Dihydroisoxazol—4—yl, 4 , 5—Dihydroisoxazol—5—yl, 2 , 5—Dihydroisoxazol—3—yl, 2 , 5—Dihydroisoxazol—4—yl , 2 , 5—Dihydroisoxazol—5—yl, 2 , 3—Dihydroisoxazol—3—yl, 2 , 3—Dihydroisoxazol—4—yl, 2,3—Dihydroisoxazol—5—yl, 4 , 5—Dihydroisothiazol—3—yl,4,5-dihydro-1H-pyrazol-3-yl, 4,5-dihydro-1H-pyrazol-4-yl, 4,5-dihydro-IH-pyrazol-5-1,5,5-dihydro-1H pyrazole-3-yl, 2,5-dihydro-lH-pyrazol-4-yl, 2,5-dihydro-lH-pyrazol-5-yl, 4,5-dihydroisoxazole-3-yl, 4,5-dihydroisoxazole 4-yl, 4,5-dihydroisoxazole-5-yl, 2,5-dihydroisoxazole-3-yl, 2,5-dihydroisoxazole-4-yl, 2,5-dihydroisoxazole-5-yl, 2,3-dihydroisoxazole 3-yl, 2,3-dihydroisoxazole-4-yl, 2,3-dihydroisoxazole-5-yl, 4,5-dihydroisothiazole-3-yl,
4 , 5-Dihydroisothiazol—4— l, 4 , 5-Dihydroisothiazol—5-yl, 2 , 5—Dihydroisothiazol—3—yl , 2 , 5—Dihydroisothiazol—4—yl, 2 , 5—Dihydroisothiazol—5—yl, 2 , 3—Dihydroisothiazol—3—yl, 2 , 3—Dihydroisothiazol—4—yl , 2 , 3—Dihydroisothiazol—5—yl , Δ-l,2-Dithiol-3-yl, Δ3-l , 2-Dithiol-4-yl ,4, 5-dihydroisothiazole-4, 1, 4, 5-dihydroisothiazole-5-yl, 2, 5-dihydroisothiazole-3-yl, 2, 5-dihydroisothiazole-4-yl, 2, 5-dihydroisothiazole-5-yl, 2,3-dihydroisothiazole-3-yl, 2,3-dihydroisothiazole-4-yl, 2,3-dihydroisothiazole-5-yl, Δ-1, 2-dithiol-3-yl, Δ 3 -l, 2-dithiol -4-yl,
Δ3-l , 2-Dithiol-5-yl , 4 , 5-Dihydrc—lH-imidazol-2-yl , 4 , 5—Dihydro—1H—imidazol—4—yl, 4 , 5—Dihydro—1H—imidazol—5—yl , 2 , 5—Dihydro-IH—imidazol—2-yl, 2 , 5—Dihydro-IH—imidazol—4—yl , 2 , 5—Dihydro—1H—imidazol—5—yl , 2 , 3—Dihydro—1H—imidazol—2—yl , 2 , 3—Dihydro—1H—imidazol—4—yl , 4 , 5—Dihydrooxazol—2—yl , 4 , 5—Dihydrooxazol—4—yl , 4 , 5—Dihydrooxazol—5—yl , 2 , 5—Dihydrooxazol—2—yl, 2 , 5—Dihydrooxazol—4—yl , 2 , 5—Dihydrooxazol—5—yl , 2 , 3—Dihydrooxazol—2—yl , 2 , 3—Dihydrooxazol—4—yl, 2 , 3—Dihydrooxazol—5—yl, 4 , 5—Dihydrothiazol—2—yl , 4 , 5—Dihydrothiazol—4—yl , 4 , 5—Dihydrothiazol—5—yl, 2 , 5—Dihydrothiazol—2—yl, 2 , 5—Dihydrothiazol—4—yl , drothiazol—5— l , 2 , 3—Dihydrothiazol—2—yl , 2 , 3—Dihydrothiazol—4—yl , 2,3-Dihydrothiazol-5-yl, 1, 3-Dioxol-2-yl, 1 , 3-Dioxol—4—yl , l,3-Dithiol-2-yl, l,3-Dithiol-4-yl, 1,3-Oxathiol-2-yl, 1, 3—Oxathiol—4—yl, 1, 3—Oxathiol—5—yl, Pyrazol—3—yl, Pyrazol—4—yl, Isoxazol—3—yl, Isoxazol—4—yl, Isoxazol—5—yl, Isothiazol—3—yl, Isothiazol—4—yl, Isothiazol—5—yl, Imidazol—2—yl, Imidazol—4—yl , Oxazol—2—yl, Oxazol—4—yl, Oxazol—5—yl, Thiazol—2—yl, Thiazol—4—yl, Thiazol—5—yl, 1,2, 3—Δ2-Oxadiazolin—4—yl , 1,2, 3—Δ2—Oxadiazolin—5—yl , l,2,4-Δ4-Oxadiazolin-3-yl, 1, 2 , 4-Δ4-Oxadiazolin-5-yl, 1,2, 4—Δ2-Oxadiazolin—3—yl , 1,2, 4—Δ2-Oxadiazolin—5—yl , 1,2, 4-Δ3-Oxadiazolin-3-yl, 1,2, 4-Δ3-Oxadiazolin-5-yl, 1,3, 4—Δ2-Oxadiazolin—2—yl , 1,3, 4—Δ2-Oxadiazolin—5—yl , 1,3, 4—Δ3—Oxadiazolin—2—yl, 1,3, 4-Oxadiazolin—2—yl , l,2,4-Δ4-Thiadiazolin-3-yl, 1, 2 , 4-Δ4-Thiadiazolin-5-yl,Δ 3- I, 2-dithiol-5-yl, 4,5-dihydrc-1H-imidazol-2-yl, 4,5-dihydro-1H-imidazole-4-yl, 4,5-dihydro-1H-imidazole -5-yl, 2.5-dihydro-IH-imidazole-2-yl, 2.5-dihydro-IH-imidazole-4-yl, 2.5-dihydro-1H-imidazole-5-yl, 2, 3 —Dihydro-1H-imidazole-2-yl, 2,3-dihydro-1H-imidazole-4-yl, 4,5-dihydrooxazole-2-yl, 4,5-dihydrooxazole-4-yl, 4,5-dihydrooxazole -5-yl, 2,5-dihydrooxazole-2-yl, 2,5-dihydrooxazole-4-yl, 2,5-dihydrooxazole-5-yl, 2,3-dihydrooxazole-2-yl, 2,3-dihydrooxazole -4-yl, 2,3-dihydrooxazole-5-yl, 4,5-dihydrothiazole-2-yl, 4,5-dihydrothiazole-4-yl, 4,5-dihydrothiazole-5-yl, 2,5-dihydrothiazole 2-yl, 2, 5-dihydrothiazole-4-yl, drothiazole-5-l, 2,3-dihydrothiazole-2-yl, 2,3-dihydrothiazol-4-yl, 2,3-dihydrothiazol-5-yl, 1,3-dioxol-2-yl, 1,3-dioxol-4-yl, 1,3-dithiol-2-yl, 1,3-dithiol-4-yl, 1,3-oxathiol-2-yl, 1,3-oxathiol-4-yl, 1,3-oxathiol-5-yl, Pyrazole-3-yl, pyrazole-4-yl, isoxazole-3-yl, isoxazole-4-yl, isoxazole-5-yl, isothiazole-3-yl, isothiazole-4-yl, isothiazole-5-yl, imidazole - 2-yl, imidazole-4-yl, oxazole-2-yl, oxazole-4-yl, oxazole-5-yl, thiazole-2-yl, thiazole-4-yl, thiazole-5-yl, 1,2, 3 — Δ 2 -oxadiazolin-4-yl, 1,2, 3 — Δ 2 -oxadiazolin-5-yl, l, 2,4-Δ 4 -oxadiazolin-3-yl, 1, 2, 4-Δ 4 - Oxadiazolin-5-yl, 1,2,4-Δ 2 oxadiazolin-3-yl, 1,2,4-Δ 2 oxadiazolin-5-yl, 1,2,4-Δ 3 oxadiazolin-3-yl , 1,2, 4-Δ 3 -oxadiazolin-5-yl, 1,3, 4-Δ 2 -oxadiazolin-2-yl, 1,3, 4-Δ 2 -oxadiazolin-5-yl, 1,3, 4-Δ 3 -oxadiazolin-2-yl, 1,3, 4-oxadiazolin-2-yl, 1,2,4-Δ 4 -thiiaziaz-3-yl, 1, 2, 4-Δ 4 -thiadiazolin-5-yl,
1.2, 4-Δ3-Thiadiazolin-3-yl, 1,2, 4-Δ3-Thiadiazolin-5-yl, 1,2, 4—Δ2-Thiadiazolin—3-yl , 1,2, 4—Δ2-Thiadiazolin—5—yl ,1.2, 4-Δ 3 -thiadiazolin-3-yl, 1,2, 4-Δ 3 -thiadiazolin-5-yl, 1,2, 4-Δ 2 -thiadiazolin-3-yl, 1,2, 4-Δ 2- thiadiazoline-5-yl,
1.3, 4-Δ2-Thiadiazolin-2-yl , 1,3, 4-Δ2-Thiadiazolin-5-yl, 1,3, 4—Δ3-Thiadiazolin—2—yl , 1,3, 4—Thiadiazolin-2-yl, l,3,2-Dioxathiolan-4-yl, 1, 2, 3-Δ2-Triazolin-4-yl, 1,2, 3-Δ2-Triazolin-5-yl , 1,2, 4-Δ2-Triazolin-3-yl , 1,2, 4-Δ2-Triazolin-5-yl , 1,2, 4-Δ3-Triazolin-3-yl , 1,2, 4—Δ3—Triazolin—5-yl , 1,2, 4—Δ1—Triazolin—2—yl , 1,2, 4-Triazolin-3-yl , 3H-1 , 2 , 4-Dithiazol-5-yl , 2H-l,3,4-Dithiazol-5-yl, 2H-1 , 3 , 4-Oxathiazol-5-yl, 1,2, 3-Oxadiazol—4—yl , 1,2, 3—Oxadiazol—5—yl, 1,2, 4-Oxadiazol—3—yl , 1,2, 4—Oxadiazol—5—yl, 1,3, 4-Oxadiazol-2—yl , 1,2, 3—Thiadiazol—4—yl , 1,2, 3—Thiadiazol-5—yl , 1,2, 4-Thiadiazol—3—yl, l,2,4-Thiadiazol-5-yl, 1,3, 4-Thiadiazolyl-2-yl, l,2,3-Triazol-4-yl, 1, 2 , 4-Triazol-3-yl, Tetrazol-5-yl;1.3, 4-Δ 2 -thiadiazolin-2-yl, 1,3, 4-Δ 2 -thiadiazolin-5-yl, 1,3, 4-Δ 3 -thiadiazolin-2-yl, 1,3, 4-thiadiazoline -2-yl, l, 3,2-dioxathiolan-4-yl, 1,2,3-Δ 2 -triazolin-4-yl, 1,2,3-Δ 2 -triazolin-5-yl, 1,2 , 4-Δ 2 -triazolin-3-yl, 1,2, 4-Δ 2 -triazolin-5-yl, 1,2, 4-Δ 3 -triazolin-3-yl, 1,2, 4-Δ 3 —Triazolin — 5-yl, 1,2, 4 — Δ 1 —Triazolin-2-yl, 1,2, 4-triazolin-3-yl, 3H-1, 2, 4-dithiazol-5-yl, 2H- l, 3,4-dithiazol-5-yl, 2H-1,3,4-oxathiazol-5-yl, 1,2,3-oxadiazole-4-yl, 1,2,3-oxadiazole-5-yl, 1,2,4-oxadiazole-3-yl, 1,2,4-oxadiazole-5-yl, 1,3,4-oxadiazol-2-yl, 1,2,3-thiadiazole-4-yl, 1,1 2,3-thiadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,3,4-thiadiazolyl-2-yl, 1,2. 3-triazol-4-yl, 1, 2, 4-triazol-3-yl, tetrazol-5-yl;
C-gebundene 6—gliedrige Ringe wie:C-linked 6-membered rings such as:
Tetrahydropyran—2—yl, Tetrahydropyran—3—yl,Tetrahydropyran-2-yl, tetrahydropyran-3-yl,
Tetrahydropyran—4—yl , Piperidin—2—yl, Piperidin—3—yl, Piperidin—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—2—yl , 1,2,3, 4—Tetrahydropyridin—6—yl , 1,2,3, 4—Tetrahydropyridin—5—yl , 1,2,3, 4—Tetrahydropyridin—4—yl, 1,2,3, 4—Tetrahydropyridi ,2,3, 4— etrahydropyridin—2—yl, 2H—5 , 6—Dihydropyran—2—yl, H—5 , 6—Dihydropyran—3—yl , 2H—5 , 6—Dihydropyran—4—yl, H—5 , 6—Dihydropyran—5—yl , 2H—5 , 6—Dihydropyran—6—yl , H—5, 6—Dihydrothiopyran—2—yl, 2H—5 , 6—Dihydrothiopyran—3—yl, H—5,6—Dihydrothiopyran—4—yl, 2H-5 , 6—Dihydrothiopyran—5—yl, H—5 , 6—Dihydrothiopyran—6—yl, 1,2,5, 6—Tetrahydropyridin—2—yl , 1,2,5, 6—Tetrahydropyridin—3—yl, 1,2,5, 6—Tetrahydropyridin—4—yl , 1,2,5, 6—Tetrahydropyridin—5—yl , 1,2,5, 6— etrahydropyridin—6—yl, 2,3,4, 5—Tetrahydropyridin—2—yl , 2,3,4, 5—Tetrahydropyridin—3—yl , 2,3,4, 5—Tetrahydropyridin—4—yl, 2,3,4, 5—Tetrahydropyridin—5—yl , 2,3,4,5-Tetrahydropyridin-6-yl, 4H-Pyran-2-yl, 4H-Pyran-3-yl, 4H—Pyran—4—yl, 4H—Thiopyran-2-yl, 4H—Thiopyran—3—yl, 4H—Thiopyran—4—yl, 1 , 4—Dihydropyridin—2—yl, 1 , 4—Dihydropyridin—3—yl , 1 , 4—Dihydropyridin—4—yl , 2H-Pyran-2-yl, 2H-Pyran-3-yl, 2H-Pyran-4-yl, 2H-Pyran-5-yl, 2H-Pyran-6-yl, 2H-Thiopyran-2-yl, 2H-Thiopyran-3-yl,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-2-yl, 1,2,3,4-tetrahydropyridine-6-yl, 1,2,3,4-tetrahydropyridine-5-yl, 1,2,3,4-tetrahydropyridine 4-yl, 1,2,3, 4-tetrahydropyridi , 2,3, 4-etrahydropyridine-2-yl, 2H-5, 6-dihydropyran-2-yl, H-5, 6-dihydropyran-3-yl, 2H-5, 6-dihydropyran-4-yl, H -5,6-dihydropyran-5-yl, 2H-5,6-dihydropyran-6-yl, H-5,6-dihydrothiopyran-2-yl, 2H-5,6-dihydrothiopyran-3-yl, H-5 , 6-dihydrothiopyran-4-yl, 2H-5, 6-dihydrothiopyran-5-yl, H-5, 6-dihydrothiopyran-6-yl, 1,2,5, 6-tetrahydropyridine-2-yl, 1,2 , 5, 6-tetrahydropyridine-3-yl, 1,2,5, 6-tetrahydropyridine-4-yl, 1,2,5, 6-tetrahydropyridine-5-yl, 1,2,5, 6-etrahydropyridine-6 -Yl, 2,3,4,5-tetrahydropyridine-2-yl, 2,3,4,5-tetrahydropyridine-3-yl, 2,3,4,5-tetrahydropyridine-4-yl, 2,3,4 , 5-tetrahydropyridine-5-yl, 2,3,4,5-tetrahydropyridin-6-yl, 4H-pyran-2-yl, 4H-pyran-3-yl, 4H-pyran-4-yl, 4H-thiopyran -2-yl, 4H-thiopyran-3-yl, 4H-thiopyran-4-yl, 1,4-dihydropyridine-2-yl, 1,4-dihydropyridine-3-yl, 1,4-dih ydropyridine-4-yl, 2H-pyran-2-yl, 2H-pyran-3-yl, 2H-pyran-4-yl, 2H-pyran-5-yl, 2H-pyran-6-yl, 2H-thiopyran 2-yl, 2H-thiopyran-3-yl,
2H-Thiopyran-4-yl, 2H-Thiopyran-5-yl, 2H-Thiopyran-6-yl, 1 , 2—Dihydropyridin—2—yl, 1 , 2—Dihydropyridin—3—yl , 1, 2—Dihydropyridin—4—yl, 1 , 2—Dihydropyridin—5—yl, 1 , 2—Dihydropyridin—6—yl , 3 , 4—Dihydropyridin—2—yl , 3,4—Dihydropyridin—3—yl, 3 , 4—Dihydropyridin—4—yl, 3 , 4—Dihydropyridin—5—yl, 3 , 4—Dihydropyridin—6—yl, 2 , 5—Dihydropyridin—2—yl , 2 , 5—Dihydropyridin—3—yl , 2 , 5—Dihydropyridin—4-yl, 2 , 5—Dihydropyridin—5—yl , 2 , 5—Dihydropyridin—6—yl, 2 , 3—Dihydropyridin—2—yl, 2 , 3—Dihydropyridin—3-yl, 2 , 3—Dihydropyridin—4—yl , 2 , 3—Dihydropyridin—5—yl , 2 , 3—Dihydropyridin—6—yl , Pyridin-2—yl, Pyridin—3—yl, Pyridin—4—yl, 1 , 3—Dioxan—2—yl , 1 , 3—Dioxan—4—yl , 1 , 3—Dioxan—5—yl , 1 , 4—Dioxan—2—yl , 1 , 3-Dithian-2-yl , 1, 3-Dithian-4-yl, 1 , 3-Dithian-5-yl , l,4-Dithian-2-yl, 1 , 3-Oxathian-2-yl, 1 , 3-Oxathian-4-yl, 1 , 3-Oxathian-5-yl , 1 , 3-Oxathian-6-yl , 1 , -Oxathian-2-yl , 1 , 4-Oxathian-3-yl , 1 , 2-Dithian-3-yl , 1, 2-Dithian-4-yl, Hexahydropyrimidin—2—yl, Hexahydropyrimidin—4—yl , Hexahydropyrimidin—5—yl, Hexahydropyrazin—2—yl , Hexahydropyridazin—3—yl, Hexahydropyridazin—4—yl,2H-thiopyran-4-yl, 2H-thiopyran-5-yl, 2H-thiopyran-6-yl, 1,2-dihydropyridine-2-yl, 1,2-dihydropyridine-3-yl, 1,2-dihydropyridine- 4-yl, 1,2-dihydropyridine-5-yl, 1,2-dihydropyridine-6-yl, 3,4-dihydropyridine-2-yl, 3,4-dihydropyridine-3-yl, 3,4-dihydropyridine 4-yl, 3,4-dihydropyridine-5-yl, 3,4-dihydropyridine-6-yl, 2,5-dihydropyridine-2-yl, 2,5-dihydropyridine-3-yl, 2,5-dihydropyridine- 4-yl, 2,5-dihydropyridine-5-yl, 2,5-dihydropyridine-6-yl, 2,3-dihydropyridine-2-yl, 2,3-dihydropyridine-3-yl, 2,3-dihydropyridine 4-yl, 2,3-dihydropyridine-5-yl, 2,3-dihydropyridine-6-yl, pyridin-2-yl, pyridine-3-yl, pyridine-4-yl, 1,3-dioxane-2- yl, 1, 3-dioxane-4-yl, 1, 3-dioxane-5-yl, 1, 4-dioxane-2-yl, 1, 3-dithian-2-yl, 1, 3-dithian-4- yl, 1, 3-dithian-5-yl, l, 4-dithian-2-yl, 1, 3-oxathian-2-yl, 1, 3-oxathian-4-yl, 1, 3-oxathian-5-yl, 1, 3-oxathian-6-yl, 1, -oxathian-2-yl, 1, 4-oxathian-3-yl, 1, 2-dithian-3-yl, 1, 2 -Dithian-4-yl, hexahydropyrimidine-2-yl, hexahydropyrimidine-4-yl, hexahydropyrimidine-5-yl, hexahydropyrazine-2-yl, hexahydropyridazine-3-yl, hexahydropyridazine-4-yl,
Tetrahydro—1 , 3—oxazin—2-yl , Tetrahydro—1 , 3-oxazin-4—yl, Tetrahydro—1 , 3—oxazin—5—yl , Tetrahydro—1 , 3—oxazin—6—yl , Tetrahydro-1 , 3-thiazin-2-y1 , Tetrahydro-1 , 3-thiazin-4-y1 , Tetrahydro-1 , 3-thiazin-5-yl, Tetrahydro-1, 3-thiazin-6-yl, Tetrahydro-l,4-thiazin-2-yl, Tetrahydro-l,4-thiazin-3-yl, Tetrahydro-1 , 4-oxazin-2-yl , Tetrahydro-1 , 4-oxazin-3-yl , Tetrahydro-1 , 2-oxazin-3— ahydro—1 , 2-oxazin—4-yl, Tetrahydro—1 , 2—oxazin—5—yl, Tetrahydro—1 , 2—oxazin—6—yl, 2H—5 , 6—Dihydro—1,2—oxazin—3—yl,Tetrahydro — 1,3-oxazin-2-yl, tetrahydro — 1,3-oxazin-4-yl, tetrahydro — 1,3-oxazin-5-yl, tetrahydro — 1,3-oxazin-6-yl, tetrahydro- 1, 3-thiazin-2-y1, tetrahydro-1, 3-thiazin-4-y1, tetrahydro-1, 3-thiazin-5-yl, tetrahydro-1, 3-thiazin-6-yl, tetrahydro-l, 4-thiazin-2-yl, tetrahydro-l, 4-thiazin-3-yl, tetrahydro-1, 4-oxazin-2-yl, tetrahydro-1, 4-oxazin-3-yl, tetrahydro-1, 2- oxazin-3-ahydro-1, 2-oxazin-4-yl, Tetrahydro-1, 2-oxazin-5-yl, tetrahydro-1, 2-oxazin-6-yl, 2H-5, 6-dihydro-1,2-oxazin-3-yl,
2H-5 6—Dihydro—1,2—oxazin—4—yl, 2H-5 6—Dihydro—1,2—oxazin—5—yl , 2H-5 6—Dihydro—1,2—oxazin—6—yl , 2H-5 6—Dihydro—1,2—thiazin—3—yl, 2H-5 6—Dihydro—1,2—thiazin—4—yl , 2H-5 6—Dihydro—1,2—thiazin—5—y1 , 2H-5 6—Dihydro—1,2—thiazin—6—yl, 4H-5 6—Dihydro—1,2—oxazin—3—yl , 4H-5 6—Dihydro—1,2—oxazin—4—yl , 4H-5 6—Dihydro—1,2—oxazin—5—yl, 4H-5 6—Dihydro—1,2—oxazin—6—yl , 4H-5 6—Dihydro—1,2—thiazin—3—yl , 4H-5 6—Dihydro—1,2—thiazin—4—yl, 4H-5 6—Dihydro—1,2—thiazin—5—yl , 4H-5 6—Dihydro—1,2—thiazin—6—yl, 2H-3 6—Dihydro—1,2—oxazin—3—yl , 2H-3 6—Dihydro—1,2—oxazin—4—yl , 2H-3 6—Dihydro—1,2—oxazin—5—yl, 2H-3 6—Dihydro—1,2—oxazin—6—yl , 2H-3 6—Dihydro—1,2—thiazin—3—yl , 2H-3 6—Dihydro—1,2—thiazin—4—yl , 2H-3 6-Dihydro—1,2—thiazin—5—yl, 2H-3 6—Dihydro—1,2—thiazin—6—yl , 2H-3 4—Dihydro—1,2—oxazin—3—yl, 2H-3 4—Dihydro—1,2—oxazin—4—yl , 2H-3 4—Dihydro—1,2—oxazin—5—yl , 2H-3 4—Dihydro—1,2—oxazin—6—yl, 2H-3 4—Dihydro—1,2—thiazin—3—yl, 2H-3 4—Dihydro—1,2—thiazin—4—yl , 2H-3 4—Dihydro—1,2—thiazin—5—yl, 2H-3 4—Dihydro—1,2—thiazin—6—yl ,2H-5 6-dihydro-1,2-oxazin-4-yl, 2H-5 6-dihydro-1,2-oxazin-5-yl, 2H-5 6-dihydro-1,2-oxazin-6-yl , 2H-5 6-dihydro-1,2-thiazine-3-yl, 2H-5 6-dihydro-1,2-thiazine-4-yl, 2H-5 6-dihydro-1,2-thiazine-5 - y1, 2H-5 6-dihydro-1,2-thiazine-6-yl, 4H-5 6-dihydro-1,2-oxazine-3-yl, 4H-5 6-dihydro-1,2-oxazine-4 -Yl, 4H-5 6-dihydro-1,2-oxazin-5-yl, 4H-5 6-dihydro-1,2-oxazin-6-yl, 4H-5 6-dihydro-1,2-thiazine 3-yl, 4H-5 6-dihydro-1,2-thiazine-4-yl, 4H-5 6-dihydro-1,2-thiazine-5-yl, 4H-5 6-dihydro-1,2-thiazine -6-yl, 2H-3 6-dihydro-1,2-oxazine-3-yl, 2H-3 6-dihydro-1,2-oxazine-4-yl, 2H-3 6-dihydro-1,2- oxazin-5-yl, 2H-3 6-dihydro-1,2-oxazin-6-yl, 2H-3 6-dihydro-1,2-thiazine-3-yl, 2H-3 6-dihydro-1,2 Thiazine-4-yl, 2H-3 6-dihydro-1,2-thiazine-5-yl, 2H-3 6-dihydro-1,2-thiazine-6-yl, 2H-3 4-yl Dihydro-1,2-oxazin-3-yl, 2H-3 4-dihydro-1,2-oxazin-4-yl, 2H-3 4-dihydro-1,2-oxazin-5-yl, 2H-3 4 Dihydro-1,2-oxazin-6-yl, 2H-3 4-dihydro-1,2-thiazine-3-yl, 2H-3 4-dihydro-1,2-thiazine-4-yl, 2H-3 4-dihydro-1,2-thiazine-5-yl, 2H-3 4-dihydro-1,2-thiazine-6-yl,
2,3,4, 5—Tetrahydropyridazin—3—yl, 2,3,4, 5—Tetrahydropyridazin—4—yl , 2,3,4, 5—Tetrahydropyridazin—5—yl , 2,3,4, 5—Tetrahydropyridazin—6—yl, 3,4,5, 6—Tetrahydropyridazin—3—yl , 3,4,5, 6—Tetrahydropyridazin—4—yl , 1,2,5, 6—Tetrahydropyridazin—3—yl, 1,2,5, 6—Tetrahydropyridazin—4—yl, 1,2,5, 6—Tetrahydropyridazin—5—yl, 1,2,5, 6—Tetrahydropyridazin—6—yl, 1,2,3, 6—Tetrahydropyridazin—3—yl , 1,2,3, 6—Tetrahydropyridazin—4—yl, 4H—5 , 6—Dihydro—1 , 3—oxazin—2—yl, 4H—5 , 6—Dihydro—1 , 3-oxaz H—5 , 6—Dihydro—1, 3—oxazin—5—yl , H—5 , 6—Dihydro—1 , 3—oxazin—6—yl , H—5 , 6—Dihydro—1 , 3—thiazin—2—yl , H—5 , 6—Dihydro—1 , 3—thiazin—4—yl , H—5 , 6—Dihydro—1 , 3—thiazin—5—yl , H—5, 6—Dihydro—1,3—thiazin—6—yl, ,4, 5—6—Tetrahydropyrimidin—2—yl, ,4,5, 6—Tetrahydropyrimidin—4—yl, ,4,5, 6—Tetrahydropyrimidin—5—yl, ,4,5, 6—Tetrahydropyrimidin—6—yl, ,2,3, 4—Tetrahydropyrazin—2—yl , ,2,3, 4—Tetrahydropyrazin—5—yl , ,2,3, 4—Tetrahydropyrimidin—2—yl, ,2,3, 4—Tetrahydropyrimidin—4—yl, ,2,3, 4—Tetrahydropyrimidin—5—yl, ,2,3, 4—Tetrahydropyrimidin—6—yl , , 3-Dihydro-l , 4-thiazin-2-yl , 2 , 3-Dihydro-l , 4-thiazin-3 -yi, , 3-Dihydro-l , 4-thiazin-5-yl , 2 , 3-Dihydrc—l , 4-thiazin-6 -yi, H-l,2-0xazin-3-yl, 2H-1, 2-0xazin-4-yl, 2H-1, 2-Oxazin-5 -yi, H-l,2-Oxazin-6-yl, 2H-1, 2-Thiazin-3-yl, 2H-1, 2-Thiazin -4-yl , H-l,2-Thiazin-5-yl, 2H-1, 2-Thiazin-6-yl, 4H-l,2-Oxazin -3-yl, H-l,2-Oxazin-4-yl, 4H-1, 2-Oxazin-5-yl, 4H-1, 2-Oxazin-6 -yi, H-1 , 2-Thiazin-3-yl, 4H-1 , 2-Thiazin-4-yl, H-l,2-Thiazin-5-yl, 4H-l,2-Thiazin-6-yl, 6H-1, 2-Oxazin -3-yl, H-l,2-Oxazin-4-yl, 6H-l,2-Oxazin-5-yl, 6H-1, 2-Oxazin-6 -yi, H-1 , 2-Thiazin-3-yl, 6H-1 , 2-Thiazin-4-yl, 6H-l,2-Thiazin-5-yl, 6H-1, 2-Thiazin-6-yl, 2H-1, 3-Oxazin -2-yl, 2H-l,3-Oxazin-4-yl, 2H-1, 3-Oxazin-5-yl, 2H-1, 3-Oxazin-6 -yi, H-1 , 3-Thiazin-2-yl, 2H-1 , 3-Thiazin-4-yl, 2H-l,3-Thiazin-5-yl, 2H-1, 3-Thiazin-6-yl, 4H-1, 3-0xazin -2-yl, 4H-l,3-Oxazin-4-yl, 4H-1, 3-Oxazin-5-yl, 4H-1, 3-Oxazin-6 -yi, 4H-1 , 3-Thiazin-2-yl, 4H-1 , 3-Thiazin-4-yl, 4H-l,3-Thiazin-5-yl, 4H-1, 3-Thiazin-6-yl, 6H-1, 3-0xazin -2-yl, 6H-l,3-Oxazin-4-yl, 6H-1, 3-Oxazin-5-yl, 6H-1, 3-Oxazin-6 -yi, 6H-l,3-Thiazin-2-yl, 6H-1, 3-Thiazin-4-yl, 6H-1,3-Thia- zin-5-yl, 6H-1, 3-Thiazin-6-yl, 2H-l,4-Oxazin-2-yl, 2H-l,4-Oxazin-3-yl, 2H-1 , 4-Oxazin-5-yl, 2H-1, 4-Oxazin-6 -yi, 2H-1 , 4-Thiazin-2-yl, 2H-1 , 4-Thiazin-3-yl, 2H-l,4-Thiazin-5-yl, 2H-1 , 4-Thiazin-6-yl, 4H-1 , 4-Oxazin -2-yl, 4H-l,4-Oxazin-3-yl, 4H-1 , 4-Thiazin-2-yl, 4H-1,4-Thiazin -3-yl, 1, 4—Dihydropyridazin—3—yl, 1, 4—Dihydropyridazin—4—yl, 1 , 4—Dihydropyridazin—5—yl , 1, 4—Dihydropyridazin—6—yl , 1 , 4—Dihydropyrazin—2—yl, 1 , 2—Dihydropyrazin—2—yl , 1 , 2—Dihydropyrazin—3—yl, 1 , 2—Dihydropyrazin—5—yl, 1 , 2—Dihydropyrazin—6—yl, 1 , 4—Dihydropyrimidin—2—yl,2,3,4,5-tetrahydropyridazine-3-yl, 2,3,4,5-tetrahydropyridazine-4-yl, 2,3,4,5-tetrahydropyridazine-5-yl, 2,3,4,5- Tetrahydropyridazine-6-yl, 3,4,5,6-tetrahydropyridazine-3-yl, 3,4,5,6-tetrahydropyridazine-4-yl, 1,2,5,6-tetrahydropyridazine-3-yl, 1,1 2,5,6-tetrahydropyridazine-4-yl, 1,2,5,6-tetrahydropyridazine-5-yl 1,2,5,6-tetrahydropyridazine-6-yl 1,2,3,6-tetrahydropyridazine 3-yl, 1,2,3,6-tetrahydropyridazine-4-yl, 4H-5,6-dihydro-1,3-oxazin-2-yl, 4H-5,6-dihydro-1,3-oxaz H-5,6-dihydro-1,3-oxazin-5-yl, H-5,6-dihydro-1,3-oxazin-6-yl, H-5,6-dihydro-1,3-thiazine 2-yl, H-5,6-dihydro-1,3-thiazine-4-yl, H-5,6-dihydro-1,3-thiazine-5-yl, H-5,6-dihydro-1, 3-thiazine-6-yl,, 4, 5-6-tetrahydropyrimidine-2-yl,, 4.5, 6-tetrahydropyrimidine-4-yl,, 4.5, 6-tetrahydropyrimidine-5-yl,, 4, 5, 6-tetrahydropyrimidine-6-yl,, 2,3, 4-tetrahydropyrazine-2-yl,, 2,3, 4-tetrahydropyrazine-5-yl,, 2,3, 4-tetrahydropyrimidine-2-yl,, 2,3, 4-tetrahydropyrimidine-4-yl,, 2,3, 4-tetrahydropyrimidine-5-yl,, 2,3, 4-tetrahydropyrimidine-6-yl,, 3-dihydro-1,4-thiazin-2 -yl, 2, 3-dihydro-l, 4-thiazin-3-yi,, 3-dihydro-l, 4-thiazin-5-yl, 2, 3-dihydrc-l, 4-thiazin-6-yi, Hl, 2-0xazin-3-yl, 2H-1, 2-0xazin-4-yl, 2H-1, 2-Oxazin-5 -yi, Hl, 2-Oxazin-6-yl, 2H-1, 2- Thiazin-3-yl, 2H-1, 2-thiazin-4-yl, Hl, 2-thiazin-5-yl, 2H-1, 2-thiazin-6-yl, 4H-1, 2-O xazin -3-yl, Hl, 2-oxazin-4-yl, 4H-1, 2-oxazin-5-yl, 4H-1, 2-oxazin-6-yi, H-1, 2-thiazin-3- yl, 4H-1, 2-thiazin-4-yl, Hl, 2-thiazin-5-yl, 4H-l, 2-thiazin-6-yl, 6H-1, 2-oxazin -3-yl, Hl, 2-oxazin-4-yl, 6H-1, 2-oxazin-5-yl, 6H-1, 2-oxazin-6-yi, H-1, 2-thiazin-3-yl, 6H-1, 2- Thiazin-4-yl, 6H-l, 2-thiazin-5-yl, 6H-1, 2-thiazin-6-yl, 2H-1, 3-oxazin-2-yl, 2H-l, 3-oxazin- 4-yl, 2H-1, 3-oxazin-5-yl, 2H-1, 3-oxazin-6-yi, H-1, 3-thiazin-2-yl, 2H-1, 3-thiazin-4- yl, 2H-l, 3-thiazin-5-yl, 2H-1, 3-thiazin-6-yl, 4H-1, 3-0xazin -2-yl, 4H-l, 3-oxazin-4-yl, 4H-1, 3-oxazin-5-yl, 4H-1, 3-oxazin-6-yi, 4H-1, 3-thiazin-2-yl, 4H-1, 3-thiazin-4-yl, 4H- l, 3-thiazin-5-yl, 4H-1, 3-thiazin-6-yl, 6H-1, 3-0xazin -2-yl, 6H-l, 3-oxazin-4-yl, 6H-1, 3-oxazin-5-yl, 6H-1, 3-oxazin-6-yi, 6H-l, 3-thiazin-2-yl, 6H-1, 3-thiazin-4-yl, 6H-1,3- Thiazin-5-yl, 6H-1, 3-thiazin-6-yl, 2H-l, 4-oxazin-2-yl, 2H-l, 4-oxazin-3-yl, 2H-1, 4- Oxazin-5-yl, 2H-1, 4-oxazin-6-yi, 2H-1, 4-thiazin-2-yl, 2H-1, 4-thiazin-3-yl, 2H-l, 4-thiazine 5-yl, 2H-1, 4-thiazin-6-yl, 4H-1, 4-oxazin-2-yl, 4H-1, 4-oxazin-3-yl, 4H-1, 4-thiazin-2-yl, 4H- 1,4-thiazine -3-yl, 1,4-dihydropyridazine-3-yl, 1,4-dihydropyridazine-4-yl, 1,4-dihydropyridazine-5-yl, 1,4-dihydropyridazine-6-yl, 1,4-dihydropyrazine-2-yl, 1,2-dihydropyrazine-2-yl, 1,2-dihydropyrazine-3-yl, 1,2-dihydropyrazine-5-yl, 1,2-dihydropyrazine-6-yl, 1,4-dihydropyrimidine-2-yl,
1 , 4—Dihydropyrimidin—4—yl , 1 , 4—Dihydropyrimidin—5—yl, 1 , 4—Dihydropyrimidin—6—y Dihydropyrimidin—2—yl, 3 , 4—Dihydropyrimidin—4—yl, 3 , 4—Dihydropyrimidin—5—yl, 3 , 4—Dihydropyrimidin—6—yl, Pyridazin—3—yl, Pyridazin—4—yl, Pyrimidin—2—yl, Pyrimidin—4—yl , Pyrimidin—5—yl, Pyrazin—2—yl, 1,3,5-Triazin—2—yl, 1,2 ,4— riazin—3—yl, 1, 2 , 4—Triazin—5—yl, 1,2 ,4—Triazin—6—yl oder 1, 2, 4 , 5—Tetra-zin—3—yl;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-gebundene 5-gliedrige Ringe wie:N-linked 5-membered rings such as:
Tetrahydropyrrol—1—yl , 2 , 3—Dihydro—IH—pyrrol—1—yl , 2 , 5-Dihydro-lH-pyrrol-l-yl , Pyrrol-1-yl ,Tetrahydropyrrole-1-yl, 2,3-dihydro-IH-pyrrole-1-yl, 2,5-dihydro-1H-pyrrole-1-yl, pyrrole-1-yl,
Tetrahydropyrazol—1—yl , Tetrahydroisoxazol—2—yl , Tetrahydroisothiazol—2—yl, Tetrahydroimidazol—1—yl, Tetrahydrooxazol—3—yl , Tetrahydrothiazol—3—yl , 4 , 5—Dihydro—IH—pyrazol—1-yl, 2 , 5-Dihydro—IH—pyrazol-1—yl, 2, 3—Dihydro—IH—pyrazol—1—yl, 2 , 5—Dihydroisoxazol—2—yl, 2 , 3—Dihydroisoxazol—2—yl, 2 , 5—Dihydroisothiazol—2—yl , 2 , 3—Dihydroisoxazol—2—yl , 4 , 5—Dihydro—IH—imidazol—1—yl , 2 , 5-Dihydro—IH—imidazol-1—yl , 2 , 3—Dihydro-IH—imidazol—1—yl , 2 , 3—Dihydrooxazol—3—yl , 2 , 3—Dihydrothiazol—3—yl , Pyrazol—1—yl, Imidazol—1—yl, 1, 2,4—Δ-Oxadiazolin—2-yl, 1,2, 4—Δ2-Oxadiazolin—4—yl , 1,2, 4-Δ3-Oxadiazolin—2-yl , 1,3, 4—Δ2—Oxadiazolin—4—yl , 1,2, 4—Δ5—Thiadiazolin—2—yl , 1,2, 4-Δ3-Thiadiazolin-2-yl , 1,2, 4-Δ2-Thiadiazolin-4-yl , 1,3, 4-Δ2—Thiadiazolin—4—yl , 1,2, 3—Δ2—Triazolin—1—yl , l,2,4-Δ2-Triazolin-l-yl, 1, 2, 4-Δ2-Triazolin-4-yl, 1,2, 4-Δ3-Triazolin-l-yl , 1,2, 4-Δ1-Triazolin-4-yl , 1,2,3-Triazol-l-yl, 1, 2 , 4-Triazol-l-yl, Tetrazol-1-yl;Tetrahydropyrazole-1-yl, tetrahydroisoxazole-2-yl, tetrahydroisothiazole-2-yl, tetrahydroimidazole-1-yl, tetrahydrooxazole-3-yl, tetrahydrothiazole-3-yl, 4,5-pyl, dihydro-IH 2,5-dihydro-IH-pyrazol-1-yl, 2,3-dihydro-IH-pyrazol-1-yl, 2,5-dihydroisoxazole-2-yl, 2,3-dihydroisoxazole-2-yl, 2, 5-dihydroisothiazole-2-yl, 2,3-dihydroisoxazole-2-yl, 4,5-dihydro-IH-imidazole-1-yl, 2,5-dihydro-IH-imidazol-1-yl, 2,3- Dihydro-IH-imidazole-1-yl, 2,3-dihydrooxazole-3-yl, 2,3-dihydrothiazole-3-yl, pyrazole-1-yl, imidazole-1-yl, 1, 2,4-Δ- Oxadiazolin-2-yl, 1,2,4-Δ 2 oxadiazolin-4-yl, 1,2,4-Δ 3 oxadiazolin-2-yl, 1,3,4-Δ 2 oxadiazolin-4-yl , 1,2, 4-Δ 5 -thiadiazolin-2-yl, 1,2, 4-Δ 3 -thiadiazolin-2-yl, 1,2,4-Δ 2 -thiadiazolin-4-yl, 1,3, 4-Δ 2 -thiadiazolin-4-yl, 1,2, 3-Δ 2 -triazolin-1-yl, 1,2-2,4-Δ 2 -T riazolin-l-yl, 1, 2, 4-Δ 2 -triazolin-4-yl, 1,2, 4-Δ 3 -triazolin-l-yl, 1,2, 4-Δ 1 -triazolin-4-yl , 1,2,3-triazol-l-yl, 1,2,4-triazol-l-yl, tetrazol-1-yl;
N—gebundene 6—gliedrige Ringe wie:N-linked 6-membered rings such as:
Piperidin—1—yl , 1,2,3, 4—Tetrahydropyridin—1—yl ,Piperidine-1-yl, 1,2,3, 4-tetrahydropyridine-1-yl,
1,2,5, 6—Tetrahydropyridin-1-yl , 1 , 4—Dihydropyridin—1—yl ,1,2,5,6-tetrahydropyridin-1-yl, 1,4-dihydropyridin-1-yl,
1 , 2—Dihydropyridin—1—yl, Hexahydropyrimidin—1—yl ,1,2-dihydropyridine-1-yl, hexahydropyrimidine-1-yl,
Hexahydropyrazin—1—yl, Hexahydropyridazin—1—yl, Tetrahydro—1,3—oxazin—3—yl, Tetrahydro—1,3—thiazin—3—yl,Hexahydropyrazine-1-yl, hexahydropyridazine-1-yl, tetrahydro-1,3-oxazine-3-yl, tetrahydro-1,3-thiazine-3-yl,
Tetrahydro-1 , 4—thiazin—4—yl , Tetrahydro-1 , 4—oxazin—4—ylTetrahydro-1,4-thiazine-4-yl, tetrahydro-1,4-oxazin-4-yl
(Morpholinyl) , Tetrahydro—1 ,2—oxazin—2—yl,(Morpholinyl), tetrahydro-1, 2-oxazin-2-yl,
2H-5 , 6-Dihydro-l , 2-oxazin-2-yl,2H-5, 6-dihydro-l, 2-oxazin-2-yl,
2H-5 , 6-Dihydro-l , 2-thiazin-2-yl , 2H-3,6-Dihydro-l,2-oxazin-2-yl,2H-5, 6-dihydro-l, 2-thiazin-2-yl, 2H-3,6-dihydro-l, 2-oxazin-2-yl,
2H-3 , 6-Dihydro-l , 2-thiazin-2-yl ,2H-3, 6-dihydro-l, 2-thiazin-2-yl,
2H-3 , 4-Dihydro-l, 2-thiazin-2-yl,2H-3,4-dihydro-1,2-thiazin-2-yl
2,3,4, 5—Tetrahydropyridazin—2—yl ,2,3,4,5-tetrahydropyridazin-2-yl,
1,2,5, 6—Tetrahydropyridazin—1—yl, 1,2,5, 6—Tetrahydropyridazin—2—yl,1,2,5,6-tetrahydropyridazine-1-yl, 1,2,5,6-tetrahydropyridazine-2-yl
1,2,3, 6—Tetrahydropyridazin—1—yl,1,2,3,6-tetrahydropyridazin-1-yl
3,4,5, 6—Tetrahydropyrimid 1,2,3, 4—Tetrahydropyrazin—1—yl, 1,2,3, 4—Tetrahydropyrimidin—1—yl , 1,2,3, 4—Tetrahydropyrimidin—3—yl,3,4,5,6-tetrahydropyrimide 1,2,3,4-tetrahydropyrazine-1-yl, 1,2,3,4-tetrahydropyrimidine-1-yl, 1,2,3,4-tetrahydropyrimidine-3-yl,
2 , 3-Dihydro-l , 4-thiazin-4-yl, 2H-1 , 2-Oxazin-2-yl , 2H-l,2-Thiazin-2-yl, 4H-1 , 4-Oxazin-4-yl, 4H-1 , 4-Thiazin-4-yl , 1 , 4—Dihydropyridazin—1—yl , 1 , 4—Dihydropyrazin—1—yl, 1,2—Dihydropyrazin—1—yl, 1 , 4—Dihydropyrimidin—1—yl oder 3 , 4—Dihydropyrimidin—3—yl ;2, 3-dihydro-l, 4-thiazin-4-yl, 2H-1, 2-oxazin-2-yl, 2H-l, 2-thiazin-2-yl, 4H-1, 4-oxazin-4- yl, 4H-1,4-thiazin-4-yl, 1,4-dihydropyridazine-1-yl, 1,4-dihydropyrazine-1-yl, 1,2-dihydropyrazine-1-yl, 1,4-dihydropyrimidine 1-yl or 3,4-dihydropyrimidine-3-yl;
sowie N-gebundene cyclische Imide wie:as well as N-linked cyclic imides such as:
Phthalsäureimid, Tetrahydrophthalsäureimid, Succinimid, Maleinimid, Glutarimid, 5-0xo-triazolin-l-yl, 5-Oxo-l , 3 , 4-oxadiazolin-4-yl oder 2, 4-Dioxo-( lH,3H)-pyrimidin-3-yl;Phthalimide, tetrahydrophthalimide, succinimide, maleimide, glutarimide, 5-0xo-triazolin-l-yl, 5-oxo-l, 3, 4-oxadiazolin-4-yl or 2,4-dioxo (lH, 3H) pyrimidine 3-yl;
wobei mit einem ankondensierten Phenylring oder mit einem C3-C6-Carbocyclus oder einem weiteren 5- bis 6-gliedrigen Heterocyclus ein bicyclisches Ringsystem ausgebildet werden kann, unda 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
wobei gegebenenfalls der Schwefel der genannten Heterocyclen zu S=0 oder S(=0)2 oxidiert sein kann.where appropriate, the sulfur of the heterocycles mentioned can be oxidized to S = 0 or S (= 0) 2 .
Alle Phenylringe bzw. Heterocyclylreste sowie alleAll phenyl rings or heterocyclyl residues as well as all
Phenylkomponenten in Phenoxy, Phenylalkyl, Phenylcarbonylalkyl, Phenylcarbonyl, Phenylalkenylcarbonyl, Phenoxycarbonyl, Phenyloxythiocarbonyl, Phenylaminocarbonyl und N—Alkyl—N—phenylaminocarbonyl, Phenylsulfonyl oder Phenoxysulfonyl bzw. Heterocyclylkomponenten in Heterocyclyloxy, Heterocyclylalkyl , Heterocyclylcarbonylalkyl, Heterocyclylcarbonyl , Heterocyclyloxythiocarbonyl , Heterocyclylalkenylcarbonyl , Heterocyclyloxycarbonyl, Heterocyclylaminocarbonyl , N—Alkyl—N—heterocyclylaminocarbonyl , Heterocyclylsulfonyl oder Heterocyclyloxysulfonyl sind, soweit nicht anders angegeben, vorzugsweise unsubstituiert oder tragen ein, zwei oder drei Halogenatome und/oder eine Nitrogruppe, einen Cyanorest und/oder einen oder zwei Methyl—, Trifluormethyl—, Methoxy— oder Trifluormethoxysubstituenten.Phenyl moieties in phenoxy, phenylalkyl, Phenylcarbonylalkyl, phenylcarbonyl, Phenylalkenylcarbonyl, phenoxycarbonyl, Phenyloxythiocarbonyl, phenylaminocarbonyl and N-alkyl-N-phenylaminocarbonyl, phenylsulfonyl or phenoxysulfonyl or Heterocyclylkomponenten in heterocyclyloxy, heterocyclylalkyl, Heterocyclylcarbonylalkyl, heterocyclylcarbonyl, Heterocyclyloxythiocarbonyl, Heterocyclylalkenylcarbonyl, heterocyclyloxycarbonyl, Heterocyclylaminocarbonyl, N —Alkyl — N — heterocyclylaminocarbonyl, heterocyclylsulfonyl or heterocyclyloxysulfonyl, unless stated otherwise, are preferably unsubstituted or carry one, two or three halogen atoms and / or a nitro group, a cyano radical and / or one or two methyl, trifluoromethyl, methoxy or Trifluormethoxysubstituenten.
Im Hinblick auf die Verwendung der erfindungsgemäßen Verbindungen der Formel I als Herbizide haben die Variablen X, R1, R2, R3 und R17 vorzugsweise folgende Bedeutungen, und zwar jeweils für sich alleine oder in Kombination:With regard to the use of the compounds of the formula I according to the invention as herbicides, the variables X, R 1 , R 2 , R 3 and R 17 preferably have the following meanings, individually or in combination:
X 0, S, S02, N-R1 oder N-NR1R17; R1 Wasserstoff, C1-C6-Alkyl, C1-C6-Halogenalkyl, C1-C6-Alkoxy, C1-C6-Halogenalkoxy, C1-C6-Alkylsulfonyl, C1-C6-Halogenalkyl- sulfonyl, C1-C6-Alkylcarbonyl, C1-C6-Halogenalkylcarbonyl,X 0, S, 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 alkylcarbonyl, C 1 -C 6 haloalkylcarbonyl,
C3-C6-Cycloalkyl, Phenyl, Heterocyclyl, Phenylsulfonyl, Heterocyclylsulfonyl, Phenylcarbonyl, Heterocyclylcarbonyl, Phe- nyl-C1-C6-alkyl , Heterocyclyl-C1-C6-alkyl,C 3 -C 6 cycloalkyl, phenyl, heterocyclyl, phenylsulfonyl, heterocyclylsulfonyl, phenylcarbonyl, heterocyclylcarbonyl, phenyl-C 1 -C 6 -alkyl, heterocyclyl-C 1 -C 6 -alkyl,
wobei die Phenyl-, Heterocyclyl- und Cycloalkylreste der vor- genannten Gruppen gegebenenfalls in der oben beschriebenenwhere the phenyl, heterocyclyl and cycloalkyl radicals of the aforementioned groups optionally in the above described
Weise substituiert sein können und beispielsweise einen, zwei oder drei Substituenten ausgewählt unter Halogen, C1-C4-Alkyl, C1-C4-Alkoxy, C1-C4-Alkylcarbonyl , Nitro, Hydroxy oder Cyano vorzugsweise ausgewählt unter Halogen, C1-C4-Alkyl, Nitro oder Cyano, tragen; besonders bevorzugt sind die Phenyl, HeterocyclylCan be substituted and, for example, one, two or three substituents selected from 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
R2 Halogen, insbesondere Fluor oder Chlor, C1-C4-Alkylsulfonyl, C1-C4-Halogenalkylsulfonyl, insbesondere Methylsulfonyl;R 2 halogen, especially fluorine or chlorine, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkylsulfonyl, especially methylsulfonyl;
R3 Wasserstoff, Fluor oder Chlor, insbesondere Wasserstoff;R 3 is hydrogen, fluorine or chlorine, especially hydrogen;
R17 Wasserstoff oder C1-C4-Alkyl, insbesondere Wasserstoff oder Methyl.R 17 is hydrogen or C 1 -C 4 alkyl, in particular hydrogen or methyl.
Hex in Formel I steht vorzugsweise für einen Rest der Formel Ha.Hex in formula I preferably represents a radical of the formula Ha.
In R1 steht Heterocyclyl vorzugsweise für ungesättigtes, aromatisches Heterocyclyl, das insbesodere C-gebunden ist.In R 1 , heterocyclyl is preferably unsaturated, aromatic heterocyclyl, which is especially C-bonded.
Insbesondere steht R1 für C1-C4-Alkyl, C1-C4-Alkoxy, C3-C6-Cycloal- kyl, C1-C4-Alkylsulfonyl, Phenyl, Phenyl-C1-C4-alkyl oder Phenylsulfonyl, wobei der Phenylring der drei letztgenannten Gruppen in der oben beschriebenen weise substituiert und insbesondere in der 4-Position Halogen oder C1-C4-Alkyl aufweisen kann.In particular, 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.
Beispiele für besonders bevorzugte Reste R1 sind: Methyl, Ethyl, n-Propyl, Isopropyl, tert. -Butyl, Methoxy, Ethoxy, n-Propoxy, Isopropoxy, tert .-Butoxy, Cyclopropyl, Phenyl, 4-Methylphenyl, 4-Chlorphenyl, Benzyl, 1- und 2-Phenylethyl, Methyl, Ethylsulfo- nyl, Phenylsulfonyl, 4-Methylphenylsulfonyl und 4-Chlorphenylsul- fonyl.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.
In N-NR1R17 haben R1 und R17 vorzugsweise die folgenden Bedeutun- gen: R1 C1-C4-Alkyl, C1-C4-Alkoxy, C3-C6-Cycloalkyl, C1-C4-Alkylsulfo- nyl, Phenyl, Phenyl-C1-C4-alkyl oder Phenylsulfonyl, wobei der Phenylring der drei letztgenannten Gruppen in der 4-Position mit Halogen oder C1-C4-Alkyl substituiert sein kann,In N-NR 1 R 17 , 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,
R17 Wasserstoff oder C1-C4-Alkyl.R 17 is hydrogen or C 1 -C 4 alkyl.
Besonders bevorzugt steht NR1R17 für C1-C4-alkylamino, Di-C1-C4-al- kylamino, Phenyl-C1-C4-alkylamino.NR 1 R 17 particularly preferably represents C 1 -C 4 -alkylamino, di-C 1 -C 4 -alkylamino, phenyl-C 1 -C 4 -alkylamino.
Bevorzugt haben R4, R5, R6 , R7, R8, R9 und R10 die folgenden Bedeutungen:R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 preferably have the following meanings:
R4 Hydroxy, Mercapto, Halogen, OR11, SR11, S02R12, OS02R12, NR15R16 und N-gebundenes Stickstoff-Heterocyclyl das partiell oder vollständig halogeniert sein kann und/oder einen, zwei oder drei der folgenden Reste tragen kann: Nitro, Cyano, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy oder C1-C4-Halogenalkoxy; wobei R11, R12, R15 und R16 die zuvor angegebenen und insbesondere die im folgenden angegebenen Bedeutungen aufweisen; R4 steht insbesondere für Hydroxy, C1-C4-Alkylcarbonyloxy, C1-C4-Alkylamino, Di-C1-C4-Alkylamino, C1-C4-Alkyl- thio, N-(C1-C4-Alkyloxy)-N-(C1-C4-alkyl)amino, C1-C4-Alkylsulfonyloxy, Phenylthio, Phenylsulfonyl, Phenylsulfonyloxy und N-gebundenem Heterocyclyl, wobei die Phenylgruppe und die Heterocyclylgruppe der vier letztgenannten Substituenten mit Halogen, Nitro, Cyano oder C1-C4-Alkyl substituiert sein kann, dieR 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 1 -C 4 -alkylsulfonyloxy, phenylthio, phenylsulfonyl, phenylsulfonyloxy and N-linked heterocyclyl, where the phenyl group and the heterocyclyl group of the last four substituents with halogen, Nitro, cyano or C 1 -C 4 alkyl can be substituted, the
Phenylgruppe vorzugsweise in der 4-Position mit Halogen oder C1-C4-Alkyl substituiert sein kann; Beispiele für R4 sind Hydroxy, Acetyl, Methylsulfonyl, Methylsulfonyloxy, Phenylthio, 4-Methylphenylthio, 4-Chlorphenylthio, Phenylsulfonyl, 4-Methylphenylsul- fonyl, 4-Chlorphenylsulfonyl, Phenylsulfonyloxy, 4-Methylphenylsulfonyloxy, 4-Chlorphenylsulfonyloxy, Dimethylamino, Diethylamino, N-Methoxy-N-methylamino, N-Ethoxy-N-methylamino, N-Methoxy-N-ethylamino, N- Ethoxy-N-ethylamino, N-Morpholin, N-Pyrrolidin undPhenyl group can preferably be substituted in the 4-position with halogen or C 1 -C 4 alkyl; Examples of 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-morpholine, N-pyrrolidine and
N-Piperidin;N-piperidine;
R5, R9 Wasserstoff oder C1-C4-Alkyl, wie Methyl, Ethyl oder Propyl; insbesondere Wasserstoff oder Methyl; R6, R8, R10 Wasserstoff oder C1-C4-Alkyl, wie Methyl, Ethyl oder Propyl; insbesondere Wasserstoff oder Methyl;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;
R7 Wasserstoff, Hydroxy, C1-C6-Alkyl, Di-(C1-C6-alk- oxy)-methyl, (C1-C6-Alkoxy)-(C1-C6-alkylthio) -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,
Di-(C1-C6-alkylthio)methyl, C1-C6-Alkylthio, C1-C6-Halogenalkylthio, C1-C6-Alkylsulfinyl, C1-C6-Halogenalkylsulfinyl, C1-C6-Alkylsulfonyl oder C1-C6-Halogenalkylsulfonyl;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;
1, 3-Dioxolan-2-yl, 1, 3-Dioxan-2-yl , 1,3-Oxa- thiolan-2-yl, 1, 3-Oxathian-2-yl, 1, 3-Dithiolan-2-yl oder 1, 3-Dithian-2-yl, wobei die sechs letztgenannten Reste durch einen, zwei oder drei C1-C4-Alkylreste substituiert sein können;1,3-dioxolan-2-yl, 1,3-dioxan-2-yl, 1,3-oxathiolan-2-yl, 1,3-oxathian-2-yl, 1,3-dithiolan-2- yl or 1, 3-dithian-2-yl, where the six last-mentioned radicals can be substituted by one, two or three C 1 -C 4 -alkyl radicals;
insbesondere Wasserstoff, Hydroxy oder C1-C4-Alkyl, wie Methyl, Ethyl oder Propyl; oderin particular hydrogen, hydroxy or C 1 -C 4 alkyl, such as methyl, ethyl or propyl; or
R6 und R8 oder R8 und R10 bilden gemeinsam eine π-Bindung oder eine C3-C5-Alkylkette, die einen bis drei Reste aus folgender Gruppe tragen kann: Halogen, Cyano, C1-C4-Alkyl, C1-C4-Halogenalkyl oder C1-C4-Alkoxy- carbonyl; oderR 6 and R 8 or R 8 and R 10 together form a π 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
R6 und R10 oder R5 und R9 bilden gemeinsam eine C1-C4-Alkyl- kette, die einen bis drei Reste aus folgender Gruppe tragen kann: Halogen, Cyano, C1-C4-Alkyl, C1-C4-Halogenalkyl oder C1-C4-Alkoxycarbonyl; oderR 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
R7 und R8 bilden gemeinsam eine -O-(CH2)p-O-, -O-(CH2)p-S- oder -S-(CH2)p-S-Kette, die durch einen bis drei Reste aus folgender Gruppe substituiert sein kann: Halogen, Cyano, C1-C4-Alkyl, C1-C4-Halogenalkyl oder C1-C4-Alkoxycarbonyl; oderR 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
R7 und R8 bilden gemeinsam mit dem Kohlenstoff, an dem sie gebunden sind, eine Carbonylgruppe aus. Die Variable p steht vorzugsweise für 2 oder 3 und die Variable q vorzugsweise für 2, 3 oder 4.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.
In R4 steht Heterocyclyl vorzugsweise für gesättigtes, N-gebunde- nes Heterocyclyl, insbesondere monocyclisches, 5- oder 6-Ring- Heterocyclyl, das gegebenenfalls ein weiteres Hetroatom, z.B. Sauerstoff oder Schwefel, Imino oder C1-C6-Alkylimino im Ring aufweist. Bevorzugte Bedeutungen für R11 bis R16 sind:In R 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:
R11 C1-C6-Alkyl, C3-C5-Alkenyl, C3-C6-Halogenalkenyl,R 11 is C 1 -C 6 alkyl, C 3 -C 5 alkenyl, C 3 -C 6 haloalkenyl,
C3-C6-Alkinyl, C1-C6-Alkylcarbonyl, C2-C6-Alkenylcarbonyl, C3-C6-Cycloalkylcarbonyl, C1-C6-Alkoxycarbonyl,C 3 -C 6 alkynyl, C 1 -C 6 alkylcarbonyl, C 2 -C 6 alkenylcarbonyl, C 3 -C 6 cycloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl,
C -C6-Alkenyloxycarbonyl , C3-C6-Alkinyloxycarbonyl , C1-C6-Alkylthiocarbonyl, C1-C6-Alkylaminocarbonyl, C3-C6-Alkenylaminocarbonyl , C3-C6-Alkinylaminocarbonyl , N , N-Di ( C1-C6-alkyl ) aminocarbonyl , N- ( C3-C6-Alken- yl)-N-(C1-C6-alkyl) -aminocarbonyl, N-(C3-C6-Alkin- yl ) -N- ( C1-C6-alkyl ) -aminocarbonyl , N- ( C1-C6-Alk- oxy) -N- ( C1-C6-alkyl ) -aminocarbonyl , N- ( C3-C6-Alken- yl ) -N- ( C1-C6-alkoxy) -aminocarbonyl , N- ( C3-C6-Alkin- yl ) -N- ( C1-C6-alkoxy) -aminocarbonyl , Di- ( C1-C6-alk- yl) -aminothiocarbonyl, C1-C6-Alkoxyimino-C1-C6-alkyl, wobei die genannten Alkyl-, Cycloalkyl- oder Alkoxyreste partiell oder vollständig halogeniert sein können und/ oder eine bis drei der folgenden Gruppen tragen können: Cyano, C1-C4-Alkoxy, C1-C4-Alkylthio, Di- (C1-C4-alkyl ) - amino, C1-C4-Alkylcarbonyl, C1-C4-Alkoxycarbonyl, Hydroxy- carbonyl, C1-C4-Alkylaminocarbonyl, Di- (C1-C4-Alkyl) aminocarbonyl, C1-C4-Alkylcarbonyloxy oder C3-C6-Cycloalkyl;C -C 6 alkenyloxycarbonyl, C 3 -C 6 alkynyloxycarbonyl, C 1 -C 6 alkylthiocarbonyl, C 1 -C 6 alkylaminocarbonyl, C 3 -C 6 alkenylaminocarbonyl, C 3 -C 6 alkynylaminocarbonyl, N, N -Di (C 1 -C 6 alkyl) aminocarbonyl, N- (C 3 -C 6 alkene-yl) -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 -alkoxy) -N- (C 1 -C 6 -alkyl) -aminocarbonyl, N- ( C 3 -C 6 -alken-yl) -N- (C 1 -C 6 -alkoxy) -aminocarbonyl, N- (C 3 -C 6 -alkynyl-yl) -N- (C 1 -C 6 -alkoxy) -aminocarbonyl, di- (C 1 -C 6 -alk- yl) -aminothiocarbonyl, C 1 -C 6 -alkoxyimino-C 1 -C 6 -alkyl, where the alkyl, cycloalkyl or alkoxy radicals mentioned are partially or completely halogenated can and / or can carry one to three of the following groups: cyano, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, di (C 1 -C 4 alkyl) amino, C 1 -C 4 -Alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl, hydroxycarbonyl, C 1 -C 4 -alkylaminocarbonyl, di- (C 1 -C 4 alkyl) aminocarbonyl, C 1 -C 4 alkylcarbonyloxy or C 3 -C 6 cycloalkyl;
Phenyl, Phenyl-C1-C6-alkyl, Phenylcarbonyl-C1-C6-alkyl, Phenylcarbonyl, Phenoxycarbonyl, Phenoxythiocarbonyl , Phenyl-C2-C6-alkenylcarbonyl, Heterocyclyl, Heterocy- clyl-C1-C6-alkyl, Heterocyclylcarbonyl-C1-C6-alkyl, Hete- rocyclylcarbonyl, Heterocyclyloxycarbonyl, Heterocyclylo- xythiocarbonyl oder Heterocyclyl-C1-C6-alkenylcarbonyl, wobei der Phenyl- oder der Heterocyclyl-Rest der 14 letztgenannten Substituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy oder C1-C4-Halogenalkoxy;Phenyl, phenyl-C 1 -C 6 -alkyl, phenylcarbonyl-C 1 -C 6 -alkyl, phenylcarbonyl, phenoxycarbonyl, phenoxythiocarbonyl, phenyl-C 2 -C 6 -alkenylcarbonyl, heterocyclyl, heterocyclic-C 1 -C 6 - alkyl, heterocyclylcarbonyl-C 1 -C 6 -alkyl, heterocyclylcarbonyl, heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl or heterocyclyl-C 1 -C 6 -alkenylcarbonyl, where the phenyl or heterocyclyl radical of the 14 last-mentioned substituents be partially or completely can and / or can carry one to 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;
insbesondere C1-C6-Alkyl, C3-C6-Alkenyl, C3-C6-Alkinyl, C1-C6-Alkylcarbonyl, C1-C6-Alkoxycarbonyl, C1-C6-Alkyl- aminocarbonyl oder N, -Di (C1-C6-alkyl) aminocarbonyl, wobei die genannten Alkyl- oder Alkoxyreste partiell oder vollständig halogeniert sein können und/oder eine bis drei der folgenden Gruppen tragen können: Cyano, C1-C4-Alkoxy, C1-C4-Alkylthio oder C1-C4-Alkoxycarbonyl;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;
Phenyl, Phenyl-C1-C6-alkyl, Phenylcarbonyl-C1-C6-alkyl, Phenylcarbonyl, Phenoxycarbonyl, Heterocyclyl, Heterocy- clyl-C1-C6-alkyl, Heterocyclylcarbonyl-C1-C6-alkyl, Hete- rocyclylcarbonyl ode cyclyloxycarbonyl, wobei der Phenyl- oder der Heterocyclyl-Rest der 10 letztgenannten Substituenten partiell oder vollständig halogeniert sein kann oder/oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy oder C1-C4-Halogenalkoxy;Phenyl, phenyl-C 1 -C 6 -alkyl, phenylcarbonyl-C 1 -C 6 -alkyl, phenylcarbonyl, phenoxycarbonyl, heterocyclyl, heterocyclic-C 1 -C 6 -alkyl, heterocyclylcarbonyl-C 1 -C 6 -alkyl, Heterocyclylcarbonyl or cyclyloxycarbonyl, the Phenyl or the heterocyclyl radical of the 10 latter substituents can be partially or completely halogenated or / and can carry one to 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;
R12 C1-C6-Alkyl, C3-C6-Alkenyl oder C3-C6-Cycloalkyl, wobei die drei genannten Reste partiell oder vollständig halogeniert sein können und/oder eine bis drei der folgenden Gruppen tragen können: Cyano, C1-C4-Alkoxy, C1-C4-Alkyl- thio, C1-C4-Alkylcarbonyl oder C1-C4-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;
Phenyl, Phenyl-C1-C4-alkyl, Heterocyclyl oder Heterocy- clyl-C1-C4-alkyl, wobei der Phenyl- oder der Heterocy- clylrest der vier letztgenannten Substituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy oder C1-C4-Alkoxycarbonyl;Phenyl, phenyl-C 1 -C 4 -alkyl, heterocyclyl or heterocyclic-C 1 -C 4 -alkyl, where the phenyl or heterocyclic radical of the four last-mentioned substituents can be partially or completely halogenated and / or one to can carry 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 ;
R13, R14 Hydroxy, C1-C6-Alkyl, C1-C6-Alkoxy, Phenyl, Phe- nyl-C1-C4-alkyl oder Phenoxy, wobei die drei letztgenannten Substituenten partiell oder vollständig halogeniert sein können und/oder einen bis drei der folgenden Reste tragen können: Nitro, Cyano, C1-C4-Alkyl, C1-C4-Halogen- alkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy oder C1-C4-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;
R15 C1-C6-Alkyl, C3-C6-Alkenyl, C3-C6-Halogenalkenyl, C3-C6-Cycloalkyl, C1-C6-Alkoxy, C3-C6-Alkenyloxy oderR 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- (C1-C6-alkyl) amino, wobei die genannten Alkyl-, Cyclo- alkyl- oder Alkoxyreste partiell oder vollständig halogeniert sein können und/oder einen bis drei der folgenden Reste tragen können: Cyano, C1-C4-Alkoxycarbonyl, C1-C4-Alkylaminocarbonyl, Di- (C1-C4-alkyl) aminocarbonyl oder C3-C6-Cycloalkyl;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;
Phenyl, Phenyl-C1-C4-alkyl, Phenylcarbonyl, Heterocyclyl, Heterocyclyl-C1-C4-alkyl oder Heterocyclylcarbonyl, wobei der Phenyl- oder Heterocyclyl-Rest der sechs letztgenannten Substituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, C1-C4-Alkyl, C1-C4-Halogen- alkyl, C1-C4-Alkoxy oder C1-C4-Halogenalkoxy;Phenyl, phenyl-C 1 -C 4 -alkyl, phenylcarbonyl, heterocyclyl, heterocyclyl-C 1 -C 4 -alkyl or heterocyclylcarbonyl, where the phenyl or heterocyclyl radical of the latter six substituents can be partially or completely halogenated and / or one 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 or C 1 -C 4 -haloalkoxy;
R16 C1-C6-Alkyl oder C3-C6-Alkenyl , Außerordentlich bevorzugt sind die Verbindungen der Formel I, worin die Variablen in Formel Ha oder Ilb unabhängig voneinander oder in Kombination miteinander die folgenden Bedeutungen haben:R 16 is C 1 -C 6 alkyl or C 3 -C 6 alkenyl, Extraordinary preference is given to the compounds of the formula I in which the variables in the formula Ha or IIb have the following meanings, independently of one another or in combination with one another:
R5, R9 Wasserstoff oder C1-C4-Alkyl;R 5 , R 9 are hydrogen or C 1 -C 4 alkyl;
R6, R8, R10 Wasserstoff oder C1-C4-Alkyl;R 6 , R 8 , R 10 are hydrogen or C 1 -C 4 alkyl;
R7 Wasserstoff, Hydroxy, C1-C6-Alkyl, insbesondere C1-C4-Alkyl, Di-(C1-C6-alkoxy) -methyl,R 7 is hydrogen, hydroxy, C 1 -C 6 alkyl, in particular C 1 -C 4 alkyl, di- (C 1 -C 6 alkoxy) methyl,
( C1-C6-Alkoxy ) - (C1-C5-alkylthio ) -methyl , Di- ( C1-C6-alkylthio ) -methyl , C1-C6-Alkylthio, C1-C6-Halogenalkylthio, C1-C6-Alkylsulfonyl oder C1-C6-Halogenalkylsulfonyl ; insbesondere Wasserstoff, Hydroxy oder C1-C6-Alkyl; oder(C 1 -C 6 alkoxy) - (C 1 -C 5 alkylthio) methyl, di (C 1 -C 6 alkylthio) methyl, C 1 -C 6 alkylthio, C 1 -C 6 - Haloalkylthio, C 1 -C 6 alkylsulfonyl or C 1 -C 6 haloalkylsulfonyl; in particular hydrogen, hydroxy or C 1 -C 6 alkyl; or
R5 und R9 oder R6 und R10 bilden gemeinsam eine C1-C4-Alkyl- kette, die einen bis drei Reste aus folgender Gruppe tragen kann: Halogen, C1-C4-Alkyl oder C1-C4-Halogen- alkyl; insbesondere bilden R6 und R10 gemeinsam eine Methylen- oder eine Ethylenbrücke aus, die einen oder zwei Reste aus folgender Gruppe tragen kann: Halogen, C1-C2-Alkyl oder C1-C2-Halogenalkyl; oderR 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
R7 und R8 bilden gemeinsam mit dem Kohlenstoff, an dem sie gebunden sind, eine Carbonylgruppe aus.R 7 and R 8 together with the carbon to which they are attached form a carbonyl group.
Ganz außerordentlich bevorzugt sind Verbindungen der Formel I, worinCompounds of the formula I in which
R5, R6, R7, R8, R9 und R10 unabhängig voneinander für Wasserstoff oder C1-C4-Alkyl stehen,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,
R7 auch für Hydroxy, C1-C4-Alkoxy, C1-C4-Alkylthio, Halogenalkoxy oder Halogenalkylthio stehen kann, oderR 7 can also represent hydroxy, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, haloalkoxy or haloalkylthio, or
R7 und R8 zusammen mit dem Kohlenstoffatom, an das sie gebunden sind auch eine Carbonylgruppe, einen 1, 3-Dioxolan-, 1 , 3-Dithiolan-, 1, 3-Oxothiolan-, 1,3-Oxothian-,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,
1, 3-Dithiolan- oder einen 1, 3-Dithian-Ring bedeuten können, wobei die 2-Position der sechs genannten Ringe mit dem C-Atom identisch ist, an das R11 und R12 gebunden sind, und/oder R5 und R9 oder R6 und R10 auch eine C1-C4-Alkylenkette bedeuten können, oderCan 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
R6 und R8 oder R8 und R9 gemeinsam eine π-Bindung ausbilden können. R 6 and R 8 or R 8 and R 9 together can form a π bond.
Ganz ausserordentlich bevorzugt sind Verbindungen der allgemeinen Formel I .1Compounds of the general formula I .1 are very particularly preferred
Figure imgf000042_0001
Figure imgf000042_0001
worin R4 und X die in jeweils einer Zeile von Tabelle A angegebene Bedeutung haben (Verbindungen I.l.l bis 1.1.135).wherein R 4 and X have the meaning given in one row of Table A (compounds III to 1.1.135).
Tabelle ATable A
Figure imgf000042_0002
Figure imgf000042_0002
Figure imgf000043_0001
Figure imgf000043_0001
Figure imgf000044_0001
Figure imgf000044_0001
Figure imgf000045_0001
Figure imgf000045_0001
Ganz ausserordentlich bevorzugt sind auch Verbindungen der allgemeinen Formel 1.2
Figure imgf000046_0001
Compounds of the general formula 1.2 are also extremely preferred
Figure imgf000046_0001
worin R4 und X die in jeweils einer Zeile von Tabelle A angegebene Bedeutung haben (Verbindungen 1.2.1 bis 1.2.135).wherein R 4 and X have the meaning given in one row of Table A (compounds 1.2.1 to 1.2.135).
Ganz ausserordentlich bevorzugt sind auch Verbindungen der allgemeinen Formel 1.3Compounds of the general formula 1.3 are also extremely preferred
Figure imgf000046_0002
Figure imgf000046_0002
worin R4 und X die in jeweils einer Zeile von Tabelle A angegebene Bedeutung haben (Verbindungen 1.3.1 bis 1.3.135).wherein R 4 and X have the meaning given in one row of Table A (compounds 1.3.1 to 1.3.135).
Ganz ausserordentlich bevorzugt sind auch Verbindungen der allgemeinen Formel 1.4Compounds of the general formula 1.4 are also extremely preferred
Figure imgf000046_0003
Figure imgf000046_0003
worin R4 und X die in jeweils einer Zeile von Tabelle A angegebene Bedeutung haben (Verbindungen 1.4.1 bis 1.4.135).wherein R 4 and X have the meaning given in one row of Table A (compounds 1.4.1 to 1.4.135).
Ganz ausserordentlich bevorzugt sind auch Verbindungen der allgemeinen Formel 1.5
Figure imgf000047_0001
Compounds of the general formula 1.5 are also extremely preferred
Figure imgf000047_0001
worin R4 und X die in jeweils einer Zeile von Tabelle A angegebene Bedeutung haben (Verbindungen 1.5.1 bis 1.5.135).wherein R 4 and X have the meaning given in one row of Table A (compounds 1.5.1 to 1.5.135).
Ganz ausserordentlich bevorzugt sind auch Verbindungen der allgemeinen Formel 1.6Compounds of the general formula 1.6 are also extremely preferred
Figure imgf000047_0002
Figure imgf000047_0002
worin R4 und X die in jeweils einer Zeile von Tabelle A angegebene Bedeutung haben (Verbindungen 1.6.1 bis 1.6.135).wherein R 4 and X have the meaning given in one row of Table A (compounds 1.6.1 to 1.6.135).
Ganz ausserordentlich bevorzugt sind auch Verbindungen der allgemeinen Formel 1.7Compounds of the general formula 1.7 are also extremely preferred
Figure imgf000047_0003
Figure imgf000047_0003
worin R4 und X die in jeweils einer Zeile von Tabelle A angegebene Bedeutung haben (Verbindungen 1.7.1 bis 1.7.135).wherein R 4 and X have the meaning given in one row of Table A (compounds 1.7.1 to 1.7.135).
Ganz ausserordentlich bevorzugt sind Verbindungen der allgemeinen Formel 1.8
Figure imgf000048_0001
Compounds of the general formula 1.8 are very particularly preferred
Figure imgf000048_0001
worin R4 und X die in jeweils einer Zeile von Tabelle A angegebene Bedeutung haben (Verbindungen 1.1.8 bis 1.8.135).wherein R 4 and X have the meaning given in one row of Table A (compounds 1.1.8 to 1.8.135).
Ganz ausserordentlich bevorzugt sind auch Verbindungen der allgemeinen Formel 1.9Compounds of the general formula 1.9 are also extremely preferred
Figure imgf000048_0002
Figure imgf000048_0002
worin R4 und X die in jeweils einer Zeile von Tabelle A angegebene Bedeutung haben (Verbindungen 1.9.1 bis 1.9.135).wherein R 4 and X have the meaning given in one row of Table A (compounds 1.9.1 to 1.9.135).
Ganz ausserordentlich bevorzugt sind auch Verbindungen der allgemeinen Formel 1.10Compounds of the general formula 1.10 are also extremely preferred
Figure imgf000048_0003
Figure imgf000048_0003
worin R4 und X die in jeweils einer Zeile von Tabelle A angegebene Bedeutung haben (Verbindungen 1.10.1 bis 1.10.135).wherein R 4 and X have the meaning given in one row of Table A (compounds 1.10.1 to 1.10.135).
Ganz ausserordentlich bevorzugt sind auch Verbindungen der allgemeinen Formel 1.11Compounds of the general formula 1.11 are also extremely preferred
*
Figure imgf000049_0001
*
Figure imgf000049_0001
worin R4 und X die in jeweils einer Zeile von Tabelle A angegebene Bedeutung haben (Verbindungen 1.11.1 bis 1.11.135).wherein R 4 and X have the meaning given in one row of Table A (compounds 1.11.1 to 1.11.135).
Ganz ausserordentlich bevorzugt sind auch Verbindungen der allgemeinen Formel 1.12Compounds of the general formula 1.12 are also extremely preferred
Figure imgf000049_0002
Figure imgf000049_0002
worin R4 und X die in jeweils einer Zeile von Tabelle A angegebene Bedeutung haben (Verbindungen 1.12.1 bis 1.12.135).wherein R 4 and X have the meaning given in one row of Table A (compounds 1.12.1 to 1.12.135).
Ganz ausserordentlich bevorzugt sind auch Verbindungen der allgemeinen Formel 1.13Compounds of the general formula 1.13 are also extremely preferred
Figure imgf000049_0003
Figure imgf000049_0003
worin R4 und X die in jeweils einer Zeile von Tabelle A angegebene Bedeutung haben (Verbindungen 1.13.1 bis 1.13.135).wherein R 4 and X have the meaning given in one row of Table A (compounds 1.13.1 to 1.13.135).
Ganz ausserordentlich bevorzugt sind auch Verbindungen der allgemeinen Formel 1.14
Figure imgf000050_0001
Compounds of the general formula 1.14 are also extremely preferred
Figure imgf000050_0001
worin R4 und X die in jeweils einer Zeile von Tabelle A angegebene Bedeutung haben (Verbindungen 1.14.1 bis 1.14.135).wherein R 4 and X have the meaning given in one row of Table A (compounds 1.14.1 to 1.14.135).
Ganz ausserordentlich bevorzugt sind Verbindungen der allgemeinen Formel 1.15Compounds of the general formula 1.15 are very particularly preferred
Figure imgf000050_0002
Figure imgf000050_0002
worin R4 und X die in jeweils einer Zeile von Tabelle A angegebene Bedeutung haben (Verbindungen 1.15.1 bis 1.15.135).wherein R 4 and X have the meaning given in one row of Table A (compounds 1.15.1 to 1.15.135).
Ganz ausserordentlich bevorzugt sind auch Verbindungen der allgemeinen Formel 1.16Compounds of the general formula 1.16 are also extremely preferred
Figure imgf000050_0003
Figure imgf000050_0003
worin R4 und X die in jeweils einer Zeile von Tabelle A angegebene Bedeutung haben (Verbindungen 1.16.1 bis 1.15.135).wherein R 4 and X have the meaning given in one row of Table A (compounds 1.16.1 to 1.15.135).
Ganz ausserordentlich bevorzugt sind auch Verbindungen der allgemeinen Formel 1.17
Figure imgf000051_0001
Compounds of the general formula 1.17 are also extremely preferred
Figure imgf000051_0001
worin R4 und X die in jeweils einer Zeile von Tabelle A angegebene Bedeutung haben (Verbindungen 1.17.1 bis 1.17.135).wherein R 4 and X have the meaning given in one row of Table A (compounds 1.17.1 to 1.17.135).
Ganz ausserordentlich bevorzugt sind auch Verbindungen der allgemeinen Formel 1.18Compounds of the general formula 1.18 are also extremely preferred
Figure imgf000051_0002
Figure imgf000051_0002
worin R4 und X die in jeweils einer Zeile von Tabelle A angegebene Bedeutung haben (Verbindungen 1.18.1 bis 1.18.135).wherein R 4 and X have the meaning given in one row of Table A (compounds 1.18.1 to 1.18.135).
Ganz ausserordentlich bevorzugt sind auch Verbindungen der allgemeinen Formel 1.19Compounds of the general formula 1.19 are also extremely preferred
Figure imgf000051_0003
Figure imgf000051_0003
worin R4 und X die in jeweils einer Zeile von Tabelle A angegebene Bedeutung haben (Verbindungen 1.19.1 bis 1.19.135).wherein R 4 and X have the meaning given in one row of Table A (compounds 1.19.1 to 1.19.135).
Ganz ausserordentlich bevorzugt sind auch Verbindungen der allgemeinen Formel 1.20
Figure imgf000052_0001
Compounds of the general formula 1.20 are also extremely preferred
Figure imgf000052_0001
worin R4 und X die in jeweils einer Zeile von Tabelle A angegebene Bedeutung haben (Verbindungen 1.20.1 bis 1.20.135).wherein R 4 and X have the meaning given in one row of Table A (compounds 1.20.1 to 1.20.135).
Ganz ausserordentlich bevorzugt sind auch Verbindungen der allgemeinen Formel 1.21Compounds of the general formula 1.21 are also extremely preferred
Figure imgf000052_0002
Figure imgf000052_0002
worin R4 und X die in jeweils einer Zeile von Tabelle A angegebene Bedeutung haben (Verbindungen 1.21.1 bis 1.21.135).wherein R 4 and X have the meaning given in one row of Table A (compounds 1.21.1 to 1.21.135).
s-/ Die Herstellung von Verbindungen der Formel I, worin R4 für Hydroxy steht, erfolgt durch Umsetzung einer aktivierten Carbonsäure IVb oder einer Carbonsäure IVa, die vorzugsweise in situ aktiviert wird, mit einem Cyclohexan-l,3-dion der Formel III zu dem Acylierungsprodukt und anschließende Umlagerung.s / Compounds of the formula I in which R 4 is hydroxy are prepared by reacting an activated carboxylic acid IVb or a carboxylic acid IVa, which is preferably activated in situ, with a cyclohexane-1,3-dione of the formula III to give the acylation product and subsequent relocation.
Figure imgf000053_0001
Figure imgf000053_0001
L1 steht für eine nucleophil verdrängbare Abgangsgruppe, wie Halogen z.B. Brom oder Chlor, N-gebundenes, aromatisches Heterocy- clyl, z.B. Imidazolyl oder Pyridyl, Carboxylat, z.B. Acetat oder Trifluoracetat etc. Die aktivierte Carbonsäure IVb kann direkt eingesetzt werden, wie im Fall der Benzoylhalogenide, oder in situ aus der Carbonsäure IVa erzeugt werden, z.B. mit Carbodiimiden wie Ethyl- (3 ' -dimethy- laminopropyl)carbodiimid, Dicyclohexylcarbodiimid, Triphenyl- phosphin/Azodicarbonsäureester, 2—Pyridindisulfid/Triphenyl- phosphin, Carbonyldiimidazol etc.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. 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.
Gegebenenfalls kann es von Vorteil sein, die Acylierungsreaktion in Gegenwart einer Base auszuführen. Die Reaktanden und die Hilfsbase werden dabei zweckmäßigerweise in äquimolaren Mengen eingesetzt. Ein geringer Überschuß der Hilfsbase z.B. 1,2 bis 1,5 Moläquivalente, bezogen auf IVa bzw. IVb, kann unter Umständen vorteilhaft sein.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.
Als Hilfsbasen eignen sich tertiäre Alkylamine, Pyridin oder Alkalimetallcarbonate. Als Lösungsmittel können z.B. chlorierte Kohlenwasserstoffe, wie Methylenchlorid oder 1, 2—Dichlorethan, aromatische Kohlenwasserstoffe, wie Toluol, Xylol oder Chlorbenzol, Ether, wie Diethylether , Methyl—tert—butylether, Tetra- hydrofuran oder Dioxan, polare aprotische Lösungsmittel, wie Acetonitril, Dimethylformamid oder Dimethylsulfoxid oder Ester wie Essigsäureethylester oder Gemische hiervon verwendet werden.Tertiary alkyl amines, pyridine or alkali metal carbonates are suitable as auxiliary bases. As 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.
Werden Halogenide als aktivierte Carbonsäurekomponente einge- setzt, so kann es zweckmäßig sein, bei Zugabe dieses Reaktionspartners die Reaktionsmischung auf etwa 0 bis 10°C abzukühlen. Anschließend rührt man bei 20 bis 100°C, vorzugsweise bei 25 bis 50°C, bis die Umsetzung vollständig ist. Die Aufarbeitung erfolgt in üblicher Weise, z.B. wird das Reaktionsgemisch auf Wasser ge- gössen, das Wertprodukt extrahiert. Als Lösungsmittel eignen sich hierfür besonders Methylenchlorid, Diethylether und Essigsäureethylester. Nach Trocknen der organischen Phase und Entfernen des Lösungsmittels kann der rohe Ester ohne weitere Reinigung zur Um- lagerung eingesetzt werden.If 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.
Die Umlagerung der Ester zu den Verbindungen der Formel I erfolgt zweckmäßigerweise bei Temperaturen von 20 bis 100°C in einem Lösungsmittel und in Gegenwart einer Base sowie gegebenenfalls mit Hilfe einer Cyanoverbindung als Katalysator.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.
Als Lösungsmittel können z.B. Acetonitril, Methylenchlorid, 1, 2—Dichlorethan, Dioxan, Essigsäureethylester, Toluol oder Gemische hiervon verwendet werden. Bevorzugte Lösungsmittel sind Acetonitril und Dioxan. Geeignete Basen sind tertiäre Amine wie Triethylamin, aromatische Amine wie Pyridin oder Alkalicarbonate, wie Natriumcarbonat oder Kaliumcarbonat, die vorzugsweise in äquimolarer Menge oder bis zu einem vierfachen Überschuß, bezogen auf den Ester, eingesetzt werden. Bevorzugt werden Triethylamin oder Alkalicarbonat verwendet, vorzugsweise in doppelt äquimolaren Verhältnis in Bezug auf den Ester.For example, 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.
Als Cyanoverbindungen kommen anorganische Cyanide, wie Natriu - cyanid oder Kaliumcyanid und organische Cyanoverbindungen, wie Acetoncyanhydrin oder Trimethylsilylcyanid in Betracht. Sie werden in einer Menge von 1 bis 50 Mol%, bezogen auf den Ester, eingesetzt. Vorzugsweise werden Acetoncyanhydrin oder Trimethylsilylcyanid, z.B. in einer Menge von 5 bis 15, vorzugsweise etwa 10 Mol%, bezogen auf den Ester, eingesetzt.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.
Die Aufarbeitung kann in an sich bekannter Weise erfolgen. Das Reaktionsgemisch wird z.B. mit verdünnter Mineralsäure, wie 5%ige Salzsäure oder Schwefelsäure, angesäuert, mit einem organischen Lösungsmittel, z.B. Methylenchlorid oder Essigsäureethylester extrahiert. Der organische Extrakt kann mit 5—10%iger Alkali- carbonatlösung, z.B. Natriumcarbonat— oder Kaliumcarbonatlösung extrahiert werden. Die wäßrige Phase wird angesäuert und der sich bildende Niederschlag abgesaugt und/oder mit Methylenchlorid oder Essigsäureethylester extrahiert, getrocknet und eingeengt.Working up can be carried out in a manner known per se. 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.
Die Acylierung der Carbonsäure IVa bzw. IVb und die nachfolgende Umlagerung zur Verbindung I kann auch als "Eintopfreaktion" , d.h. ohne Isolierung des Esters durchgeführt werden.The 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.
B, Die Darstellung von Verbindungen der Formel I mit R4 = Halogen erfolgt durch Umsetzung von Cyclohexenon-Derivaten der Formel I (mit R4 = Hydroxy) mit Halogenierungsmitteln:B, Compounds of the formula I with R 4 = halogen are prepared by reacting cyclohexenone derivatives of the formula I (with R 4 = hydroxy) with halogenating agents:
Figure imgf000055_0001
Figure imgf000055_0001
Hier und im folgenden steht "la" für eine Verbindung der allgemeinen Formel I, worin Hex für einen Rest der allgemeinen Formel Ha steht und "lb" entsprechend für eine Verbindung der allgemeinen Formel I, worin Hex für einen Rest Ilb steht. Als Halogenierungsmittel eignen sich beispielsweise Phosgen, Diphosgen, Triphosgen, Thionylchlorid, Oxalylchlorid, Phosphoroxychlorid, Phosphorpentachlorid, Mesylchlorid, Chlormethylen-N, N-dimethylammoniumchlorid, Oxalylbromid , Phosphoroxybromid etc .Here and below, "la" stands for a compound of the general formula I in which hex represents a radical of the general formula Ha and "lb" correspondingly for a compound of the general formula I in which hex represents a radical Ilb. 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.
Die Darstellung von Verbindungen der Formel I mit R4 = OR11, OS02R12, OPOR13R14 oder OPSR13R14 erfolgt durch Umsetzung von Cyclohexenon-Derivaten der Formel I (mit R4 = Hydroxy) mit Al- kylierungs-, Sulfonylierungs- bzw. Phosphonylierungsmitteln Vα, Vß, Vγ beziehungsweise Vδ.Compounds of the formula I with R 4 = OR 11 , OS0 2 R 12 , OPOR 13 R 14 or OPSR 13 R 14 are prepared by reacting cyclohexenone derivatives of the formula I (with R 4 = hydroxy) with alkylation , Sulfonylating or phosphonylating agents Vα, Vß, Vγ or Vδ.
Figure imgf000056_0001
Figure imgf000056_0001
L2 steht für eine nucleophil verdrängbare Abgangsgruppe, wie Halogen, z.B. Chlor oder Brom, Hetaryl, z.B. Imidazolyl, Carboxylat, z.B. Acetat, oder Sulfonat, z.B. Mesylat oder Triflat 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.
Die Verbindungen der Formel Vα, Vß, Vγ oder Vδ können direkt eingesetzt werden wie z.B. im Fall der Carbonsäurehalogenide oder in situ erzeugt werden, z.B. aktivierte Carbonsäuren (mit Carbonsäure und Dicyclohexylcarbodiimid etc.).The compounds of the formula Vα, Vß, Vγ or Vδ 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.).
Die Darstellung von Verbindungen der Formel I mit R4 = OR11, SR11, POR13R14, NR15R16, ONR15R16 oder N-gebundenes Heterocyclyl erfolgt durch Umsetzung von Verbindungen der Formel I mit R4 = Halogen, OSO2R12 mit Verbindungen der Formel Vlα, Vlß, Vlγ, Vlδ, Vlε oder Vlη, gegebenenfalls in Gegenwart einer Base oder unter vorangehender Salzbildung.
Figure imgf000057_0001
Compounds of the formula I with R 4 = OR 11 , SR 11 , POR 13 R 14 , NR 15 R 16 , ONR 15 R 16 or N-linked heterocyclyl are prepared by reacting compounds of the formula I with R 4 = halogen, OSO 2 R 12 with compounds of the formula Vlα, Vlß, Vlγ, Vlδ, Vlε or Vlη, optionally in the presence of a base or with prior salt formation.
Figure imgf000057_0001
Die Darstellung von Verbindungen der Formel I mit R4 = SOR12, S02R12 erfolgt beispielsweise durch Umsetzung von Verbindungen der Formel I mit R4 = SR12 mit einem Oxidationsmittel .Compounds of the formula I with R 4 = SOR 12 , S0 2 R 12 are prepared, for example, by reacting compounds of the formula I with R 4 = SR 12 with an oxidizing agent.
Figure imgf000057_0002
Figure imgf000057_0002
Als Oxidationsmittel kommen beispielsweise m-Chlorperbenzoe- säure, Peroxyessigsäure, Trifluorperoxyessigsäure, Wasserstoffperoxid, ggf. in Gegenwart eines Katalysators wie Wol- framat, in Betracht.Examples of suitable oxidizing agents are m-chloroperbenzoic acid, peroxyacetic acid, trifluoroperoxyacetic acid, hydrogen peroxide, if appropriate in the presence of a catalyst such as tungstate.
Für die unter den Punkten B bis E genannten Reaktionen gelten folgende Bedingungen:The following conditions apply to the reactions mentioned under points B to E:
Die Ausgangsverbindungen werden in der Regel im äquimolaren Verhältnis eingesetzt. Es kann aber auch von Vorteil sein, die eine oder andere Komponente im Überschuß einzusetzen.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.
Gegebenenfalls kann es von Vorteil sein, die Umsetzungen in Gegenwart einer Base durchzuführen. Die Reaktanden und die Base werden dabei zweckmäßigerweise in äquimolaren Mengen eingesetzt.It may be advantageous to carry out the reactions in the presence of a base. The reactants and the base are expediently used in equimolar amounts.
Im Hinblick auf die Verfahren C und D kann es unter Umständen vorteilhaft sein, ein Überschuß der Base z.B. 1,5 bis 3 Moläquivalente jeweils bezogen auf das Edukt einzusetzen.With regard to processes C and D it may be advantageous to use an excess of the base e.g. Use 1.5 to 3 molar equivalents each based on the starting material.
Als Basen eignen sich tertiäre Alkylamine, wie Triethylamin, aromatische Amine, wie Pyridin, Alkalimetallcarbonate, z.B. Natriumcarbonat oder Kaliumcarbonat, i etallhydrogencarbonate, wie Natriumhydrogencarbonat und Kaliumhydrogencarbonat , Alkalimetall- alkoholate wie Natriummethanolat, Natriumethanolat , Kalium-tert- butanolat oder Alkalimetallhydride, z.B. Natriumhydrid. Bevorzugt verwendet werden Triethylamin oder Pyridin.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.
Als Lösungsmittel kommen z.B. chlorierte Kohlenwasserstoffe, wie Methylenchlorid oder 1 ,2—Dichlorethan, aromatische Kohlenwasserstoffe, z.B. Toluol, Xylol oder Chlorbenzol, Ether, wie Diethylether, Methyl—tert—butylether, Tetrahydrofuran oder Dioxan, polare aprotische Lösungsmittel, wie Acetonitril, Dimethylform- amid oder Dimethylsulfoxid oder Ester, wie Essigsäureethylester, oder Gemische hiervon in Betracht.Examples of solvents are 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.
In der Regel liegt die Reaktionstemperatur im Bereich von 0°C bis zur Höhe des Siedepunktes des Reaktionsgemisches.As a rule, the reaction temperature is in the range from 0 ° C. to the boiling point of the reaction mixture.
Die Aufarbeitung kann in an sich bekannter Weise zum Produkt hin erfolgen.The product can be worked up in a manner known per se.
In Abhängigkeit von den Reaktionsbedingungen können bei den Verfahren B bis D die Verbindungen Ia, Ib oder Gemische hiervon gebildet werden. Letztere können durch klassische Trennmethoden, wie z.B. Kristallisation, Chromatographie etc., getrennt werden.Depending on the reaction conditions, 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.
Die als Ausgangsmaterialien verwendeten Cyclohexandione der Formel III sind bekannt oder können nach an sich bekannten Verfahren hergestellt werden (z.B. EP-A 71 707, EP-A 142 741, EP-A 243 313, US 4,249,937, WO 92/13821).The 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).
Die Alkylierungsmittel Vα, Sulfonylierungsmittel Vß, Phosphonylie- rungsmittel Vγ beziehungsweise Vδ, sowie die Verbindungen Vlα, Vlß, Vlγ, Vlδ und Vlε sind ebenfalls bekannt oder können nach bekannten Verfahren hergestellt werden.The alkylating agents Vα, sulfonylating agents Vß, phosphonizing agents Vγ and Vδ, and the compounds Vlα, Vlß, Vlγ, Vlδ and Vlε are also known or can be prepared by known processes.
Die Carbonsäuren der allgemeinen Formel IVa beziehungsweise ihre aktivierten Derivate IVb lassen sich in Analogie zu bekannten Verfahren herstellen. Die Carbonsäuren IVa und ihre aktivierten Derivate IVb sind neu und ebenfalls Gegenstand der vorliegenden Erfindung.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.
Die Herstellung der Carbonsäuren der Formel IVa mit X = 0 (Verbindungen der Formel IVa.O) erfolgt durch Umsetzung der Verbindungen der Verbindungen der Formel V, worin die Reste L gleich oder verschieden sein können und für eine nucleophil verdrängbare Abgangsgruppefür Mesylat, Triflat oder Halogen, z.B. Brom stehen, und die Reste R2 und R3 die zuvor genannten Bedeutungen aufweisen, im wäßrigen alkalischen Milieu (siehe z.B. Kirmse et al. J. Am Chem. Soc. 1986, 108, 6045-6046):The carboxylic acids of the formula IVa with X = 0 (compounds of the formula IVa.O) are prepared by reacting the compounds of the compounds of the formula V, in which the radicals L can be the same or different and for a nucleophilically displaceable leaving group for mesylate, triflate or halogen , for example bromine, and the radicals R 2 and R 3 have the meanings given above, in an aqueous alkaline medium (see, for example, Kirmse et al. J. Am Chem. Soc. 1986, 108, 6045-6046):
Figure imgf000059_0001
Figure imgf000059_0001
Als Base kommen Alkalimetallhydroxide wie Natriumhydroxid oder Kaliumhydroxid, Alkalimetallcarbonate wie Natriumcarbonat oder Kaliumcarbonat oder Acetate wie Natriumacetat in Betracht.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.
Die Herstellung der Carbonsäuren der Formel IVa mit X = S (Verbindungen der Formel IVa.S) erfolgt durch Umsetzung der Verbindungen der Formel V, worin L gleich oder verschieden sein können und für eine nucleophil verdrängbare Abgangsgruppe wie Mesylat, Triflat oder Halogen, z.B. Brom stehen, und die Reste R2 und R3 die zuvor genannten Bedeutungen aufweisen, mit Schwefelwasserstoff oder seinen Alkali- oder Erdalkalimetallsalzen wie Natriumsulfid oder Natriumhydrogensulfid gegebenenfalls in Gegenwart ei- ner Base (siehe z.B. Lon-Tang et al. J. Org. Chem, 1984, 49, 1027-1030; Kreher et al. Chem. ber. 1991, 124, 645):The carboxylic acids of the formula IVa with X = S (compounds of the formula IVa.S) are prepared by reacting the compounds of the formula V, in which L can be the same or different and for a nucleophilically displaceable leaving group such as mesylate, triflate or halogen, for example bromine and the radicals R 2 and R 3 have the meanings given above, with hydrogen sulfide or its alkali metal or alkaline earth metal salts such as sodium sulfide or sodium hydrogen sulfide, if appropriate in the presence of a base (see, for example, Lon-Tang et al. J. Org. Chem. 1984, 49, 1027-1030; Kreher et al. Chem. Ber. 1991, 124, 645):
Figure imgf000059_0002
Figure imgf000059_0002
Als Base eignen sich z.B. Alkalimetallcarbonate wie Natriumcarbonat oder Kaliumcarbonat, Alkalimetallhydrogencarbonate wie Natri- umhydrogencarbonat oder tertiäre Amine wie z.B. Triethylamin oder Pyridin.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.
Die Herstellung der Carbonsäuren der Formel IVa mit X = S(O)n (Verbindungen der Formel IVa. SO) erfolgt durch Umsetzung der Verbindungen der Verbindungen der Formel IVa.S mit Oxidationsmit- teln:
Figure imgf000060_0001
The carboxylic acids of the formula IVa with X = S (O) n (compounds of the formula IVa. SO) are prepared by reacting the compounds of the compounds of the formula IVa.S with oxidizing agents:
Figure imgf000060_0001
Als Oxidationsmittel eignen sich beispielsweise m-Chlorperbenzoe- säure, Peroxyessigsäure, Trifluorperoxyessigsäure, Wasserstoffperoxid, gegebenenfalls in Gegenwart eines Katalysators wie Wolfra- mat, Halogene, oder Sauerstoff, vorzugsweise in Gegenwart von Photosensibilisatoren. Durch Wahl des Oxidationsmittels oder der Stöchiometrie der eingesetzten Reagenzien kann man Sulfoxide oder Sulfone gezielt herstellen (zur Oxidation von Thioethern zu Sul- foxiden und Sulfonen siehe auch J. March, Advanced Organic Che- mistry, 4th ed. Wiley 1992, S. 1201 ff u. dort zitierte Literatur) .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. By choosing the oxidizing agent or the stoichiometry of the reagents used, sulfoxides or sulfones can be produced specifically (for the oxidation of thioethers to sulfoxides and sulfones see also J. March, Advanced Organic Chemistry, 4th ed. Wiley 1992, p. 1201 ff and literature cited there).
Die Herstellung der Carbonsäuren der Formel IVa mit X = N-R1 (Verbindungen der Formel IVa.N) erfolgt durch Umsetzung der Verbindungen der Formel V, worin die Reste R1, R2 und R3 die zuvor genannten Bedeutungen aufweisen, mit primären Aminen oder primären Amiden, gegebenenfalls in Gegenwart einer Hilfsbase oder einem Überschuß des Amins (siehe beispielsweise US 4,652,573; Bornstein et al. Org. Synth. Coll Vol V, 1973, 1064; Kreher et al . Chem.- Ztg. 1988, 112, 85-92):The carboxylic acids of the formula IVa with X = NR 1 (compounds of the formula IVa.N) are prepared by reacting the compounds of the formula V, in which the radicals R 1 , R 2 and R 3 have the meanings given above, with primary amines or primary amides, optionally in the presence of an auxiliary base or an excess of the amine (see, for example, US 4,652,573; Bornstein et al. Org. Synth. Coll Vol V, 1973, 1064; Kreher et al. Chem. - Ztg. 1988, 112, 85- 92):
Figure imgf000060_0002
Figure imgf000060_0002
Als Hilfsbase eignen sich beispielsweise Alkalimetallcarbonate, wie Natriumcarbonat oder Kaliumcarbonat, tertiäre Amine wie z.B. Triethylamin oder Pyridin, Alkalimetallhydride wie z.B. Natrium- hydrid oder Kaliumhydrid oder sterisch anspruchsvolle Alkohole wie z.B. Kalium-tert-Butanolat .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.
Die Herstellung der Carbonsäuren der Formel IVa mit X = N-NR1R17 (Verbindungen der Formel iVa.NN) erfolgt anlog zur Herstellung von Verbindungen IVa.N durch Umsetzung der Verbindungen der Formel V, worin die Reste R1, R2 und R3 die zuvor genannten Bedeutun- gen aufweisen, mit primären Hydrazinen oder primären Hydraziden, gegebenenfalls in Gegenwart einer Hilfsbase oder einem Überschuß des Hydrazins:The carboxylic acids of the formula IVa with X = N-NR 1 R 17 (compounds of the formula iVa.NN) are prepared analogously to the preparation of compounds IVa.N by reacting the compounds of the formula V, in which the radicals R 1 , R 2 and R 3 has the meanings mentioned above have genes, with primary hydrazines or primary hydrazides, optionally in the presence of an auxiliary base or an excess of the hydrazine:
Figure imgf000061_0001
Figure imgf000061_0001
Die Herstellung von Verbindungen der Formel V kann in Analogie zu bekannten Verfahren erfolgen. Die Herstellung von Verbindungen der allgemeinen Formel V mit L = Halogen gelingt ausgehend von 2 , 3-Dimethylbenzoesäuren der Formel VI, worin R2 und R3 die zuvorgenannten Bedeutungen aufweisen beispielsweise durch radikalische Halogenierung der Methylgruppen in VI gemäß folgendem Schema.Compounds of the formula V can be prepared analogously to known processes. Compounds of the general formula V with L = halogen can be prepared starting from 2,3-dimethylbenzoic acids of the formula VI, in which R 2 and R 3 have the meanings given above, for example by radical halogenation of the methyl groups in VI according to the following scheme.
Figure imgf000061_0002
Figure imgf000061_0002
Als Halogenierungsmittel eignen sich beispielsweise Chlor, Brom, N-Chloramin, N-Chlorsuccinimid, N-Bromsuccinimid. Vorzugsweise erfolgt die Reaktion in Anwesenheit eines Radikalstarters. Im Hinblick auf die Radikalstarter kommen unter anderem Benzoylpero- xid oder Azobisisobutyronitril in Betracht. Es ist aber auch mög- lieh, die Reaktion unter Bestrahlung mit geeigneten Strahlungsquellen wie UV-Hg-Niederdruck- oder Hg-Hochdrucklampen und/oder unter Erwärmen durchzuführen ohne einen externen Radikalstarter durchzuführen. Verfahren zur Halogenierung von Verbindungen mit ortho-Xylolstruktur sind in der Literatur beschrieben (siehe z.B. Box et al, Heterocycles 1990, 31, 1261-1270; Röhrich et al. J. Org. Chem. 1992, 57, 2374; Hanack et al . Chem. Ber. 1992, 125; Hanack, ebenda 1243-1247).Examples of 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. With regard to the radical initiators, benzoyl peroxide or azobisisobutyronitrile, among others, are suitable. However, it is also possible to carry out the reaction under irradiation with 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. Methods for halogenating compounds with an ortho-xylene structure are described in the literature (see, for example, Box et al, Heterocycles 1990, 31, 1261-1270; Röhrich et al. J. Org. Chem. 1992, 57, 2374; Hanack et al. Chem. Ber. 1992, 125; Hanack, ibid. 1243-1247).
Die substituierten 2 , 3-Dimethylbenzoesäuren der Formel VI sind ihrerseits bekannt (siehe z.B. EP-A 894 792; Merchant et al. J. Am. Chem. Soc . 1964, 2258-2261 - auf diese Schriften wird hiermit in vollem Umfang Bezug genommen) oder können analog zu den dort beschriebenen Herstellungsverfahren hergestellt werden.The substituted 2,3-dimethylbenzoic acids of the formula VI are in turn known (see, for example, EP-A 894 792; Merchant et al. J. Am. Chem. Soc. 1964, 2258-2261 - reference is hereby made to these documents referred to in full) or can be produced analogously to the manufacturing processes described therein.
Die im folgenden angegebenen Beispiele dienen der Erläuterung der Erfindung.The examples given below serve to illustrate the invention.
Herstellungsbeispiele :Manufacturing examples:
1. Synthese der Vorprodukte1. Synthesis of the preliminary products
1.1 Synthese von 7-Sulfonylmethyl-l, 3-dihydrobenzo[c] thiophen- 4-carbonsäure1.1 Synthesis of 7-sulfonylmethyl-1,3-dihydrobenzo [c] thiophene-4-carboxylic acid
a) Brom-2 , 3-dimethyl-4-thiomethylbenzola) Bromo-2, 3-dimethyl-4-thiomethylbenzene
Zu einer Lösung aus 509 g (3,33 mol) 2 , 3-Dimethyl-l-thiome- thylbenzol in 3 1 Eisessig gab man innerhalb 3 h bei Raumtemperatur 592 g (3,69 mol) Brom und ließ noch 3 h nachreagieren. Der ausgefallene Feststoff wurde abgesaugt und verwor- fen. Das Filtrat versetzte man mit 300 g Natriumacetat und entfernte das Lösungsmittel. Der Rückstand wurde in Dichlor- methan aufgenommen und nacheinander zweimal mit Natriumhydro- gencarbonatlösung und einmal mit Kochsalzlösung gewaschen. Die organische Phase trocknete man über Natriumsulfat und entfernte anschließend das Lösungsmittel. Zurück blieb die Titelverbindung als farbloser Feststoff. Ausbeute: 530 g (69%).592 g (3.69 mol) of bromine were added to a solution of 509 g (3.33 mol) of 2, 3-dimethyl-l-thiomethylbenzene in 3 l of glacial acetic acid at room temperature in the course of 3 h and the mixture was left to react for a further 3 h. The precipitated solid was suctioned off and discarded. 300 g of sodium acetate were added to the filtrate and the solvent was removed. The residue was taken up in dichloromethane and washed successively twice with sodium hydrogen carbonate solution and once with brine. The organic phase was dried over sodium sulfate and then the solvent was removed. The title compound remained as a colorless solid. Yield: 530 g (69%).
!H-NMR (CDC13) δ: 7,22 (d, IH); 6,84 (d, IH) ; 2,24 (s, 3H); 2,20 (s, 3H); 2,18 (s, 3H). ! H NMR (CDC1 3 ) δ: 7.22 (d, IH); 6.84 (d, IH); 2.24 (s, 3H); 2.20 (s, 3H); 2.18 (s, 3H).
b) 2, 3-Dimethyl-4-thiomethylbenzoesäureb) 2,3-dimethyl-4-thiomethylbenzoic acid
106 g (4,4 mol) Magnesiumspäne in 100 ml THF wurden mit 1 ml 1, 2-Dibromethan und 11 g Bromethan in 20 ml THF angeätzt. Anschließend wurden bei Raumtemperatur 907 g (3,8 mol) des Produktes aus Stufe a) in 1,5 1 THF innerhalb von 1 3/4 h zugetropft und danach eine weitere Stunde unter Rückfluß erhitzt. Dann leitete man bei -10°C 1750 g Kohlendioxid als Gas ein und rührte die erhaltene Suspension über Nacht bei Raumtemperatur. Man rührte die so erhaltene Mischung in ein Gemisch aus 2,3 1 Wasser, 800 ml konz. Salzsäure und 1 kg Eis ein und saugte den entstehenden Niederschlag ab. Man wusch zweimal mit je 1 1 Petrolether nach und trocknete den so erhaltenen Feststoff im Vakuum. Ausbeute: 647 g (87%). Schmp. :210°C106 g (4.4 mol) of magnesium shavings in 100 ml of THF were etched with 1 ml of 1,2-dibromoethane and 11 g of bromoethane in 20 ml of THF. 907 g (3.8 mol) of the product from stage a) in 1.5 l of THF were then added dropwise at room temperature in the course of 1 3/4 hours and the mixture was then heated under reflux for a further hour. Then 1750 g of carbon dioxide were passed in as a gas at -10 ° C. and the suspension obtained was stirred overnight at room temperature. The mixture thus obtained was stirred in a mixture of 2.3 l of water, 800 ml of conc. Hydrochloric acid and 1 kg of ice and sucked off the resulting precipitate. It was washed twice with 1 liter of petroleum ether and the solid thus obtained was dried in vacuo. Yield: 647 g (87%). Mp: 210 ° C
c ) 2 , 3-Dimethyl-4-sulfonylmethylbenzoesäurec) 2, 3-Dimethyl-4-sulfonylmethylbenzoic acid
Zu einer Suspension von 65 g (330 mmol) des Produktes aus Stufe b) und 10 g (30 mmol) Natriumwolframatdihydrat in 550 ml Eisessig tropfte man 136 g (1,2 mol) Wasserstoffperoxid (30%ig) zu und rührte über Nacht nach. Man gab 500 ml Wasser zu und saugte den entstandenen Niederschlag ab. Ausbeute: 67 g (88%) . Schmp.: 220°C136 g (1.2 mol) of hydrogen peroxide (30%) were added dropwise to a suspension of 65 g (330 mmol) of the product from stage b) and 10 g (30 mmol) of sodium tungstate dihydrate in 550 ml of glacial acetic acid and the mixture was stirred overnight , 500 ml of water were added and the precipitate formed was filtered off with suction. Yield: 67 g (88%). Mp: 220 ° C
d) 2, 3-Bis (brommethyl) - -sulfonylmethylbenzoesäured) 2,3-bis (bromomethyl) -sulfonylmethylbenzoic acid
Zu einem Gemisch von 57 g (250 mmol) des Produktes aus Stufe c), 2 g konz. Schwefelsäure, 208 g (1,2 mol) Bromwasserstoff- säure (47%ig) und 600 ml Chlorbenzol gab man bei 70°C in Portionen 190 g (560 mmol) Wasserstoffperoxid (10%) und rührte noch 1 h nach. Man ließ erkalten und saugte den entstandenen Niederschlag ab. Anschließend wurde der Rückstand mit Petro- lether digeriert und getrocknet. Man erhielt so die Titelverbindung in einer Ausbeute von 79 g (82%). Schmp.: 167°CTo a mixture of 57 g (250 mmol) of the product from step c), 2 g of conc. Sulfuric acid, 208 g (1.2 mol) hydrobromic acid (47%) and 600 ml chlorobenzene were added in portions at 70 ° C in 190 g (560 mmol) hydrogen peroxide (10%) and stirring was continued for 1 h. The mixture was allowed to cool and the precipitate formed was filtered off with suction. The residue was then digested with petroleum ether and dried. The title compound was thus obtained in a yield of 79 g (82%). Mp: 167 ° C
e ) 7-Sulfonylmethyl-1 , 3-dihydrobenzo [ c ] thiophen-4-carbonsäure (Vorstufe 1)e) 7-sulfonylmethyl-1, 3-dihydrobenzo [c] thiophene-4-carboxylic acid (precursor 1)
Zu einer Lösung aus 0,8 g (2,1 mmol) des Produktes aus Stufe d) in 30 ml Ethanol, 15 ml THF und 1 , 5 ml Wasser gab man 80 mg (2,1 mmol) Natriumhydroxid und 0,4 g (5,1 mmol) Natriumsulfid (60-62%ig). Nach 2 h am Rückfluß wurde das Lösungsmittel entfernt, der Rückstand in Wasser aufgenommen und mit Salzsäure angesäuert. Hierbei fiel die Titelverbindung als Feststoff aus, der abgesaugt und getrocknet wurde. Ausbeute: 0,4 g (74%). Schmp.: 280-282°C80 mg (2.1 mmol) of sodium hydroxide and 0.4 g were added to a solution of 0.8 g (2.1 mmol) of the product from stage d) in 30 ml of ethanol, 15 ml of THF and 1.5 ml of water (5.1 mmol) sodium sulfide (60-62%). After 2 hours at reflux, the solvent was removed, the residue was taken up in water and acidified with hydrochloric acid. The title compound precipitated as a solid, which was filtered off and dried. Yield: 0.4 g (74%). Mp: 280-282 ° C
1.2 Synthese von 7-Sulfonylmethyl-1, 3-dihydrobenzo[c] furan-4- carbonsäure (Vorstufe 2)1.2 Synthesis of 7-sulfonylmethyl-1,3-dihydrobenzo [c] furan-4-carboxylic acid (precursor 2)
Ein Gemisch aus 182 g (472 mmol) des Produkts aus Stufe 1.1 d) , 38 g Natriumacetat und 2,8 1 Wasser wurde 5 h auf 90°C erhitzt. Man filtrierte heiß und ließ das Filtrat über Nacht bei Raumtemperatur stehen. Hierbei kristallisierte die Titelverbindung als Feststoff aus, der abgesaugt und getrocknet wurde. Ausbeute: 60 g (53%) . Schmp.: 245-250°CA mixture of 182 g (472 mmol) of the product from stage 1.1 d), 38 g of sodium acetate and 2.8 l of water was heated to 90 ° C. for 5 h. The mixture was filtered hot and the filtrate was left to stand at room temperature overnight. The title compound crystallized out as a solid, which was filtered off and dried. Yield: 60 g (53%). Mp: 245-250 ° C
1.3 In analoger Weise wurde ausgehend von 4-Chlor-2 , 3-dimethyl- benzoesäure die 7-Chlor-l, 3-dihydrobenzo[c ] furan-4-carbon- säure (Vorstufe 3; Verbindung IVa mit R2 = Chlor, R3 = H und x = 0) und ausgehend von 4-Fluor-2 , 3-dimethylbenzoesäure die 7-Fluor-l , 3-dihydro[c] furan-4-carbonsäure (Vorstufe 4; Verbindung IVa mit R2 = Fluor, R3 = H und x = 0) hergestellt.1.3 Starting from 4-chloro-2, 3-dimethylbenzoic acid, 7-chloro-1,3-dihydrobenzo [c] furan-4-carboxylic acid (precursor 3; compound IVa with R 2 = chlorine, R 3 = H and x = 0) and, starting from 4-fluoro-2,3-dimethylbenzoic acid, 7-fluoro-1,3-dihydro [c] furan-4-carboxylic acid (precursor 4; compound IVa with R 2 = fluorine , R 3 = H and x = 0).
2. Synthese der Endprodukte2. Synthesis of the end products
2.1 2-{ ( 7-Sulfonylmethyl-l, 3-dihydrobenzo[c ] furan-4-yl)' carbonyl}-l-hydroxy-cyclohex-l-en-3-on (Beispiel 1)2.1 2- {(7-sulfonylmethyl-l, 3-dihydrobenzo [c] furan-4-yl) 'carbonyl} -l-hydroxy-cyclohex-l-en-3-one (Example 1)
2,0 g (8,3 mmol) der Vorstufe 2, gelöst in 30 ml Acetonitril, wurden mit 0,9 g (8,3 mmol) Cyclohexan-1, 3-dion und 1,7 g (8,3 mmol) N,N-Dicyclohexylcarbodiimid versetzt und 3 h bei Raumtemperatur gerührt. Anschließend wurden 1,7 g (16,5 mmol) Triethylamin und 0,4 ml Trimethylsilylcyanid zugesetzt und weitere 4 h bei Raumtemperatur gerührt. Man fügte je 50 ml 2%ige Sodalösung und Ethylacetat zu und saugte den Niederschlag ab. Die alkalische wäßrige Phase wurde einmal mit Ether extrahiert und mit Salzsäure auf pH 4 eingestellt. Hierbei kristallisierte die Titelverbindung aus. Ausbeute: 1,4 g (50%). Schmp.: 155-156°C2.0 g (8.3 mmol) of precursor 2, dissolved in 30 ml of acetonitrile, were mixed with 0.9 g (8.3 mmol) of cyclohexane-1, 3-dione and 1.7 g (8.3 mmol) N, N-dicyclohexylcarbodiimide were added and the mixture was stirred at room temperature for 3 h. Then 1.7 g (16.5 mmol) of triethylamine and 0.4 ml of trimethylsilyl cyanide were added and the mixture was stirred for a further 4 h at room temperature. 50 ml of 2% sodium carbonate solution and ethyl acetate were added and the precipitate was filtered off with suction. The alkaline aqueous phase was extracted once with ether and adjusted to pH 4 with hydrochloric acid. The title compound crystallized out. Yield: 1.4 g (50%). Mp: 155-156 ° C
b) Synthese von 2-{ ( 7-Sulfonylmethyl-1, 3-dihydrobenzo[c ] furan- 4-yl)-carbonyl}.-l-chlorcyclohex-l-en-3-on (Beispiel 2)b) Synthesis of 2- {(7-sulfonylmethyl-1,3-dihydrobenzo [c] furan- 4-yl) carbonyl} .- l-chlorocyclohex-l-en-3-one (Example 2)
Zu einer Lösung aus 0,9 g (2,7 mmol) der Verbindung aus Beispiel 1 in 20 ml Dichlormethan und 3 Tropfen Dimethylformamid wurde 0,68 g (5,4 mmol) Oxalylchlorid getropft und der Ansatz wurde anschließend 2 h unter Rückfluß erhitzt. Man gab auf0.68 g (5.4 mmol) of oxalyl chloride was added dropwise to a solution of 0.9 g (2.7 mmol) of the compound from Example 1 in 20 ml of dichloromethane and 3 drops of dimethylformamide, and the mixture was then heated under reflux for 2 h , They gave up
Wasser, trocknete die organische Phase über Natriumsulfat und entfernte das Lösungsmittel. Hierbei fiel die Titelverbindung als gelber Feststoff an. Ausbeute: 0,9 g (94%) . Schmp.: 172-174°CWater, dried the organic phase over sodium sulfate and removed the solvent. The title compound was obtained as a yellow solid. Yield: 0.9 g (94%). Mp: 172-174 ° C
2.3 2-{ ( 7-Sulfonylmethyl-1, 3-dihydrobenzo[c ] furan-4-yl) - carbonyl}-l- (N-methoxy-N-methyl ) aminocyclohex-l-en-3-on (Beispiel 3)2.3 2- {(7-Sulfonylmethyl-1, 3-dihydrobenzo [c] furan-4-yl) carbonyl} -l- (N-methoxy-N-methyl) aminocyclohex-1-en-3-one (Example 3 )
82 mg (0,85 mmol) N,0-Dimethylhydroxylaminhydrochlorid in 10 ml Dimethylsulfoxid wurden mit 140 mg (1,69 mmol) Natriumhy- drogencarbonat versetzt. Anschließend gab man portionsweise 300 mg (0,85 mmol) der Verbindung aus Beispiel 2 zu und rührte weitere 2 h. Man gab auf Wasser und extrahierte mit Ethylacetat. Die organische Phase wurde über Natriumsulfat getrocknet und eingeengt. Der Rückstand wurde an Kieselgel mit Cyclohexan und Ethylacetat (2:3) als Eluent chromatogra- phiert. Nach Einengen des Eluats erhielt man die Titelverbindung als farblosen Feststoff. Ausbeute: 0,1 g (31%) .82 mg (0.85 mmol) of N, 0-dimethylhydroxylamine hydrochloride in 10 ml of dimethyl sulfoxide were treated with 140 mg (1.69 mmol) of sodium hy- bicarbonate added. Then 300 mg (0.85 mmol) of the compound from Example 2 were added in portions and the mixture was stirred for a further 2 h. The mixture was poured into water and extracted with ethyl acetate. The organic phase was dried over sodium sulfate and concentrated. The residue was chromatographed on silica gel with cyclohexane and ethyl acetate (2: 3) as the eluent. After concentration of the eluate, the title compound was obtained as a colorless solid. Yield: 0.1 g (31%).
1H-NMR (CDC13) δ: 7,85 (d, IH); 7,78 (d, IH); 5,50 (s, 2H); 5,40 (s, 2H); 3,28 (s, 3H); 3,18 (s, 3H); 3,02 (s, 3H); 2,50 (t, 2H); 2,42 (t, 2H); 2,12 (m, 2H). 1 H NMR (CDC1 3 ) δ: 7.85 (d, IH); 7.78 (d, IH); 5.50 (s, 2H); 5.40 (s, 2H); 3.28 (s. 3H); 3.18 (s, 3H); 3.02 (s, 3H); 2.50 (t, 2H); 2.42 (t, 2H); 2.12 (m, 2H).
2.4 2-{ ( 7-Sulfonylmethyl-l, 3-dihydrobenzo[ c ] thiophen-4-yl ) -carbo- nyl}-l-hydroxy-cyclohex-l-en-3-on (Beispiel 4)2.4 2- {(7-sulfonylmethyl-1,3-dihydrobenzo [c] thiophene-4-yl) carbonyl} -l-hydroxycyclohex-1-en-3-one (Example 4)
Ein Gemisch aus 0,7 g (2,7 mmol) der Vorstufe 1, 0,3 g (2,7 mmol) 1, 3-Cyclohexandion, 0,56 g (2,7 mmol) N,N-Dicyclohexyl- carbodiimid und 30 ml Acetonitril wurde über Nacht bei Raumtemperatur gerührt. Anschließend gab man 0,55 g (5,4 mmol) Triethylamin und 0,05 ml Trimethylsilylcyanid zu und rührte weitere 4 h. Man gab auf je 50 ml 2%ige Sodalösung und Ethylacetat und saugte den Niederschlag ab. Die wäßrige Phase wurde einmal mit Ether gewaschen und mit Salzsäure auf pH 4 eingestellt. Der gebildete Niederschlag wurde abgesaugt und getrocknet. Chromatographie an Kieselgel lieferte das Produkt.A mixture of 0.7 g (2.7 mmol) of precursor 1, 0.3 g (2.7 mmol) of 1,3-cyclohexanedione, 0.56 g (2.7 mmol) of N, N-dicyclohexylcarbodiimide and 30 ml of acetonitrile was stirred at room temperature overnight. Then 0.55 g (5.4 mmol) of triethylamine and 0.05 ml of trimethylsilyl cyanide were added and the mixture was stirred for a further 4 h. It was added to 50 ml of 2% sodium carbonate solution and ethyl acetate and the precipitate was filtered off with suction. The aqueous phase was washed once with ether and adjusted to pH 4 with hydrochloric acid. The precipitate formed was suction filtered and dried. Chromatography on silica gel provided the product.
Ausbeute: 170 mg (18%). Schmp.: 177-179°CYield: 170 mg (18%). Mp: 177-179 ° C
In der nachfolgenden Tabelle 1 sind neben den vorstehend beschriebenen Verbindungen der Beispiele 1, 2, 3 und 4 noch weitere Cyclohexenon-Derivate der Formel Ia aufgeführt, die auf analoge Weise ausgehend von Vorstufe 1, 2, 3 und 4 hergestellt wurden.In addition to the compounds of Examples 1, 2, 3 and 4 described above, 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.
Figure imgf000065_0001
Tabelle 1
Figure imgf000065_0001
Table 1
Figure imgf000066_0001
Figure imgf000066_0001
Figure imgf000067_0002
Figure imgf000067_0002
1-H-NMR-Daten: 1 H NMR data:
Verbindung aus Beispiel Nr. 12: 1,8 (m, 2H); 2,17 (d, 2H); 2,95 (t, 2H); 3,05 (s, 3H); 5,4 (s, 4H); 7,35 (m, 4H); 7,58 (d, IH); 7,89 (d, IH).Compound from Example No. 12: 1.8 (m, 2H); 2.17 (d. 2H); 2.95 (t, 2H); 3.05 (s. 3H); 5.4 (s, 4H); 7.35 (m. 4H); 7.58 (d, IH); 7.89 (d, IH).
Figure imgf000067_0001
Figure imgf000067_0001
Verbindung aus Beispiel Nr. 25: 1,7 ( , 2H); 1,91 (t, 2H); 2,2 (t, 2H); 2,92 (t, IH); 3,02 (t, IH);Compound from Example No. 25: 1.7 (, 2H); 1.91 (t, 2H); 2.2 (t, 2H); 2.92 (t, IH); 3.02 (t, IH);
3,22 (s, 3H); 3,26 (s, 3H); 5,1 (s, 2H); 5,5 (s, 2H); 7,25 (d, IH); 7,41 (d, IH).3.22 (s, 3H); 3.26 (s, 3H); 5.1 (s, 2H); 5.5 (s, 2H); 7.25 (d, IH); 7.41 (d, IH).
Verbindung aus Beispiel Nr. 30: 2,1 (m, 2H); 2,45 (dt, 4H); 3,15 (s, 3H); 3,24 (s, 3H); 5,15 (s, 2H);Compound from Example No. 30: 2.1 (m, 2H); 2.45 (dt, 4H); 3.15 (s, 3H); 3.24 (s, 3H); 5.15 (s. 2H);
5,45 (s, 2H); 6,98 (t, IH); 7,6 (q, IH).5.45 (s. 2H); 6.98 (t, IH); 7.6 (q, IH).
Verbindung aus Beispiel Nr. 31: 1,17 (s, 6H); 2,42 (t, 2H); 2,47 (t, 2H); 3,15 (s, 3H); 3,24 (s, 3H);Compound from Example No. 31: 1.17 (s, 6H); 2.42 (t, 2H); 2.47 (t, 2H); 3.15 (s, 3H); 3.24 (s, 3H);
5,14 (s, 2H); 5,42 (s, 2H); 6,98 (t, IH); 7,65 (q, IH) .5.14 (s, 2H); 5.42 (s, 2H); 6.98 (t, IH); 7.65 (q, IH).
Verbindung aus Beispiel Nr. 1,07 (s, 6H); 2,25 (s, 2H); 2,37 (s, 2H); 5,18 (s, 2H); 5,47 (s, 2H); 7,0Compound from Example No. 1.07 (s, 6H); 2.25 (s, 2H); 2.37 (s, 2H); 5.18 (s. 2H); 5.47 (s, 2H); 7.0
(t, IH); 7,4 (m, 5H); 7,59 (q, IH).(t, IH); 7.4 (m, 5H); 7.59 (q, IH).
Figure imgf000068_0001
Figure imgf000068_0001
Die Verbindungen der Formel I und deren landwirtschaftlich brauchbaren Salze eignen sich sowohl als Isomerengemische als auch in Form der reinen Isomeren - als Herbizide. Die herbiziden Mittel, die Verbindungen der Formel I enthalten, bekämpfen Pflanzenwuchs auf Nichtkulturflächen sehr gut, besonders bei hohen Aufwandmengen. In Kulturen wie Weizen, Reis, Mais, Soja und Baumwolle wirken sie gegen Unkräuter und Schadgräser, ohne die Kulturpflanzen nennenswert zu schädigen. Dieser Effekt tritt vor al- lern bei niedrigen Aufwandmengen auf.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.
In Abhängigkeit von der jeweiligen Applikationsmethode können die Verbindungen der Formel I bzw. sie enthaltenden herbiziden Mittel noch in einer weiteren Zahl von Kulturpflanzen zur Beseitigung unerwünschter Pflanzen eingesetzt werden. In Betracht kommen beispielsweise folgende Kulturen:Depending on the particular application method, 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:
Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec . altissima, Beta vulgaris spec . rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum,Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea libericaus), Cucumodison , Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum,
(Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium) , Helianthus annuus, Hevea brasiliensis , Hordeum vulgäre, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec, Manihot esculenta, Medicago sativa, Musa spec, 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 officinarum, Seeale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgäre), Theobroma cacao, Trifo- lium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera und Zea mays .(Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgäre, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersica, Musus spec, manus spec, Medicinal specimen, Malus spec. 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.
Darüber hinaus können die Verbindungen Ia bzw. Ib auch in Kultu- ren, die durch Züchtung einschließlich gentechnischer Methoden gegen die Wirkung von Herbiziden tolerant sind, verwandt werden.In addition, 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.
Die Applikation der herbiziden Mittel bzw. der Wirkstoffe kann im Vorauflauf- oder im Nachauflaufverfahren erfolgen. Sind die Wirk- Stoffe für gewisse Kulturpflanzen weniger verträglich, so können Ausbringungstechniken angewandt werden, bei welchen die herbiziden Mittel mit Hilfe der Spr e so gespritzt werden, daß
Figure imgf000070_0001
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
Figure imgf000070_0001
kylphenyl- , Tributylphenylpolyglykolether , Alkylarylpolyetheral- kohole, Isotridecylalkohol, Fettalkoholethylenoxid-Kondensate, ethoxyliertes Rizinusöl, Polyoxyethylenalkylether oder Polyoxy- propylenalkylether , Laurylalkoholpolyglykoletheracetat, Sorbite- ster, Lignin-Sulfitablaugen oder Methylcellulose in Betracht.kylphenyl, tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ether or polyoxypropylene alkyl ether, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignin sulfite waste liquor or methyl lignin.
Pulver-, Streu- und Stäubemittel können durch Mischen oder gemeinsames Vermählen der wirksamen Substanzen mit einem festen Trägerstoff hergestellt werden.Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
Granulate, z.B. Umhüllungs-, Imprägnierungs- und Homogengranulate können durch Bindung der Wirkstoffe an feste Trägerstoffe hergestellt werden. Feste Trägerstoffe sind Mineralerden wie Kieselsäuren, Kieselgele, Silikate, Talkum, Kaolin, Kalkstein, Kalk, Kreide, Bolus, Löß, Ton, Dolomit, Diatomeenerde, Calcium- und Magnesiumsulfat, Magnesiumoxid, gemahlene Kunststoffe, Düngemittel, wie Ammoniumsulfat, Ammoniumphosphat, Ammoniumnitrat, Harnstoffe und pflanzliche Produkte wie Getreidemehl, Baumrinden-, Holz- und Nußschalenmehl, Cellulosepulver oder andere feste Trägerstoffe.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.
Die Konzentrationen der Wirkstoffe Ia bzw. Ib in den anwendungsfertigen Zubereitungen können in weiten Bereichen variiert werden. Die Formulierungen enthalten im allgemeinen 0,001 bis 98 Gew.-%, vorzugsweise 0,01 bis 95 Gew.-%, mindestens eines Wirk- Stoffs. Die Wirkstoffe werden dabei in einer Reinheit von 90% bis 100%, vorzugsweise 95% bis 100% (nach NMR-Spektrum) eingesetzt.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).
Die erfindungsgemäßen Verbindungen Ia bzw. Ib können beispielsweise wie folgt formuliert werden:The compounds Ia or Ib according to the invention can be formulated, for example, as follows:
I 20 Gewichtsteile der Verbindung Nr. 4 werden in einer Mischung gelöst, die aus 80 Gewichtsteilen alkyliertem Benzol, 10 Gewichtsteilen des Anlagerungsproduktes von 8 bis 10 Mol Ethylenoxid an 1 Mol Ölsäure-N-monoethanolamid, 5 Gewichtsteilen Calciumsalz der Dodecylbenzolsulfonsäure und 5 Gewichtsteilen des Anlagerungsproduktes von 40 Mol Ethylenoxid an 1 Mol Ricinusöl besteht. Durch Ausgießen und feines Verteilen der Lösung in 100 000 Gewichtsteilen Wasser erhält man eine wäßrige Dispersion, die 0,02 Gew.-% des Wirkstoffs enthält.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. By pouring the solution into 100,000 parts by weight of water and finely distributing it therein, an aqueous dispersion is obtained which contains 0.02% by weight of the active ingredient.
II 20 Gewichtsteile der Verbindung Nr. 1 werden in einer Mischung gelöst, die aus 40 Gewichtsteilen Cyclohexanon, 30 Gewichtsteilen Isobutanol, 20 Gewichtsteilen des Anla- gerungsproduktes von 7 Mol Ethylenoxid an 1 Mol Isooctyl- phenol und 10 Gewichtsteilen des Anlagerungsproduktes von 40 Mol Ethylenoxid a Ricinusöl besteht. Durch Ein- gießen und feines Verteilen der Lösung in 100 000 Gewichtsteilen Wasser erhält man eine wäßrige Dispersion, die 0,02 Gew.-% des Wirkstoffs enthält.II 20 parts by weight of compound no. 1 are dissolved in a mixture which consists of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 mol of ethylene oxide and 1 mol of isooctylphenol and 10 parts by weight of the adduct of 40 mol of ethylene oxide a Castor oil is made up. Through a- pouring and finely distributing the solution in 100,000 parts by weight of water gives an aqueous dispersion which contains 0.02% by weight of the active ingredient.
III 20 Gewichtsteile des Wirkstoffs Nr. 1 werden in einer Mischung gelöst, die aus 25 Gewichtsteilen Cyclohexanon, 65 Gewichtsteilen einer Mineralölfraktion vom Siedepunkt 210 bis 280°C und 10 Gewichtsteilen des Anlagerungsproduktes von 40 Mol Ethylenoxid an 1 Mol Ricinusöl besteht. Durch Eingießen und feines Verteilen der Lösung inIII 20 parts by weight of active ingredient No. 1 are dissolved in a mixture consisting of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction with a boiling point of 210 to 280 ° C. and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. By pouring and finely distributing the solution in
100 000 Gewichtsteilen Wasser erhält man eine wäßrige Dispersion, die 0,02 Gew.-% des Wirkstoffs enthält.100,000 parts by weight of water give an aqueous dispersion which contains 0.02% by weight of the active ingredient.
IV 20 Gewichtsteile des Wirkstoffs Nr. 4 werden mit 3 Ge- wichtsteilen des Natriumsalzes der Diisobutylnaphthalin- sulfonsäure, 17 Gewichtsteilen des Natriumsalzes einer Ligninsulfonsäure aus einer Sulfit-Ablauge und 60 Gewichtsteilen pulverförmigem Kieselsäuregel gut vermischt und in einer Hammermühle vermählen. Durch feines Vertei- len der Mischung in 20 000 Gewichtsteilen Wasser erhält man eine Spritzbrühe, die 0,1 Gew.-% des Wirkstoffs enthält.IV 20 parts by weight of active ingredient No. 4 are mixed well with 3 parts by weight of the sodium salt of diisobutylnaphthalenesulphonic acid, 17 parts by weight of the sodium salt of lignosulphonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel and ground in a hammer mill. By finely distributing the mixture in 20,000 parts by weight of water, a spray liquor is obtained which contains 0.1% by weight of the active ingredient.
V 3 Gewichtsteile des Wirkstoffs Nr. 4 werden mit 97 Ge- wichtsteilen feinteiligem Kaolin vermischt. Man erhält auf diese Weise ein Stäubemittel, das 3 Gew.-% des Wirkstoffs enthält.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.
VI 20 Gewichtsteile des Wirkstoffs Nr. 4 werden mit 2 Ge- wichtsteilen Calciumsalz der Dodecylbenzolsulfonsäure, 8VI 20 parts by weight of active ingredient no. 4 are mixed with 2 parts by weight of calcium salt of dodecylbenzenesulfonic acid, 8
Gewichtsteilen Fettalkohol-polyglykolether, 2 Gewichtsteilen Natriumsalz eines Phenol-Harnstof -Formaldehyd- Kondesates und 68 Gewichtsteilen eines paraffinischen Mineralöls innig vermischt. Man erhält eine stabile ölige Dispersion.Parts by weight of fatty alcohol polyglycol ether, 2 parts by weight of sodium salt of a phenol-urea-formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil. A stable oily dispersion is obtained.
VII 1 Gewichtsteil der Verbindung Nr. 1 wird in einer Mischung gelöst, die aus 70 Gewichtsteilen Cyclohexanon, 20 Gewichtsteilen ethoxyliertem Isooctylphenol und 10 Ge- wichtsteilen ethoxyliertem Rizinusöl besteht. Man erhält ein stabiles Emulsionskonzentrat.VII 1 part by weight of compound no. 1 is dissolved in a mixture consisting of 70 parts by weight of cyclohexanone, 20 parts by weight of ethoxylated isooctylphenol and 10 parts by weight of ethoxylated castor oil. A stable emulsion concentrate is obtained.
VIII 1 Gewichtsteil der Verbindung Nr. 1 wird in einer Mischung gelöst, die aus 80 Gewichtsteilen Cyclohexanon und 20 Gewichtsteilen Wettol ® EM 31 (nicht ionischer Emul- gator auf der Basis von ethoxyliertem Ricinusöl). Man erhält ein stabiles Emulsionskonzentrat.VIII 1 part by weight of compound no. 1 is dissolved in a mixture which consists of 80 parts by weight of cyclohexanone and 20 parts by weight of Wettol® EM 31 (non-ionic emulsion). gator based on ethoxylated castor oil). A stable emulsion concentrate is obtained.
Zur Verbreiterung des WirkungsSpektrums und zur Erzielung syner- gistischer Effekte können die Cyclohexenonderivate als s Ia bzw. Ib mit zahlreichen Vertretern anderer herbizider oder wachstumsregulierender Wirkstoffgruppen gemischt und gemeinsam ausgebracht werden. Beispielsweise kommen als Mischungspartner 1,2, 4-Thiadia- zole, 1 , 3 , 4-Thiadiazole, Amide, Aminophosphorsäure und deren De- rivate, Aminotriazole, Anilide, ( Het) -Aryloxyalkansäure und deren Derivate, Benzoesäure und deren Derivate, Benzothiadiazinone, 2-Aroyl-l, 3-cyclohexandione, Hetaryl-Aryl-Ketone, Benzylisoxazo- lidinone, Meta-CF3-phenylderivate, Carbamate, Chinolincarbonsäure und deren Derivate, Chloracetanilide, Cyclohexan-1 , 3-dionderi- vate, Diazine, Dichlorpropionsäure und deren Derivate, Dihydro- benzofurane, Dihydrofuran-3-one, Dinitroaniline, Dinitrophenole, Diphenylether , Dipyridyle, Halogencarbonsäuren und deren Derivate, Harnstoffe, 3-Phenyluracile, Imidazole, Imidazolinone, N- Phenyl-3 , 4 , 5 , 6-tetrahydrophthalimide, Oxadiazole, Oxirane, Phe- nole, Aryloxy- oder Heteroaryloxyphenoxypropionsäureester , Pheny- lessigsäure und deren Derivate, Phenylpropionsäure und deren Derivate, Pyrazole, Phenylpyrazole, Pyridazine, Pyridincarbonsäure und deren Derivate, Pyri idylether , Sulfonamide, Sulfonylharn- stoffe, Triazine, Triazinone, Triazolinone, Triazolcarboxamide, Uracile in Betracht.In order to broaden the spectrum of activity and to achieve synergistic effects, 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. For example, 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, dihydrobenzofurans, dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3, 4, 5, 6-tetrahydrophthalide , Oxadiazoles, oxiranes, phenols, aryloxy- or heteroaryloxyphenoxypropionic acid esters, phenylacetic acid and its derivatives, phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and their der Derivatives, pyridyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides, uracils into consideration.
Außerdem kann es von Nutzen sein, die Verbindungen Ia bzw. Ib allein oder in Kombination mit anderen herbiziden auch noch mit weiteren Pflanzenschutzmitteln gemischt, gemeinsam auszubringen, beispielsweise mit Mitteln zur Bekämpfung von Schädlingen oder phytopathogenen Pilzen bzw. Bakterien. Von Interesse ist ferner die Mischbarkeit mit Mineralsalzlösungen, welche zur Behebung von Ernährungs- und Spurenelementmängeln eingesetzt werden. Es können auch nichtphytotoxische Öle und Ölkonzentrate zugesetzt werden. Die Aufwandmengen an Wirkstoff betragen je nach Bekämpfungsziel, Jahreszeit, Zielpflanzen und Wachstumsstadium 0,001 bis 3, vorzugsweise 0,01 bis 1,0 kg/ha aktive Substanz (a. S.).It 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. Also of interest is 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. Depending on the control target, the season, the target plants and the growth stage, the active compound application rates are 0.001 to 3, preferably 0.01 to 1.0 kg / ha of active substance (see p.).
Teil Bpart B
Anwendungsbeispieleapplications
Die herbizide Wirkung der Cyclohexenonderivate als s der Formel ia bzw. Ib ließ sich durch Gewächshausversuche zeigen: Als Kulturgefäße dienten Plastiktöpfe mit lehmigem Sand mit etwa 3,0% Humus als Substrat. Die Samen der Testpflanzen wurden nach Arten getrennt eingesät.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.
5 Bei Vorauflaufbehandlung wurden die in Wasser suspendierten oder emulgierten Wirkstoffe direkt nach Einsaat mittels fein verteilender Düsen aufgebracht. Die Gefäße wurden leicht beregnet, um Keimung und Wachstum zu fördern, und anschließend mit durchsichtigen Plastikhauben abgedeckt, bis die Pflanzen angewachsen wa- 10 ren. Diese Abdeckung bewirkt ein gleichmäßiges Keimen der Testpflanzen, sofern dies nicht durch die Wirkstoffe beeinträchtigt wurde .5 In pre-emergence treatment, 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.
Zum Zweck der Nachauflaufbehandlung wurden die Testpflanzen je 15 nach Wuchsform erst bis zu einer Wuchshöhe von 3 bis 15 cm angezogen und dann mit den in Wasser suspendierten oder emulgierten Wirkstoffen behandelt. Die Testpflanzen wurden dafür entweder direkt gesät und in den gleichen Gefäßen aufgezogen oder sie wurden erst als Keimpflanzen getrennt angezogen und einige Tage vor der 20 Behandlung in die Versuchsgefäße verpflanzt. Die Aufwandmenge für die Nachauflaufbehandlung betrug 0,5, 0,25 und 0,125 kg/ha aktive Substanz .For the purpose of post-emergence treatment, the 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. For this purpose, 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.
Die Pflanzen wurden artenspezifisch bei Temperaturen von 10 bis 25 25°C bzw. 20 bis 35°C gehalten. Die Versuchsperiode erstreckte sich über 2 bis 4 Wochen. Während dieser Zeit wurden die Pflanzen gepflegt, und ihre Reaktion auf die einzelnen Behandlungen wurde ausgewertet.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.
30 Bewertet wurde nach einer Skala von 0 bis 100. Dabei bedeutet 100 kein Aufgang der Pflanzen bzw. völlige Zerstörung zumindest der oberirdischen Teile und 0 keine Schädigung oder normaler Wach- stumsverlauf .30 was rated 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.
35 Die in den Gewächshausversuchen verwendeten Pflanzen setzten sich aus folgenden Arten zusammen:35 The plants used in the greenhouse experiments are composed of the following species:
Bayercode Deutscher Name Englischer NameBayercode German name English name
ZEAMX Mais cornZEAMX corn corn
40 ABUTH Chinesischer Hanf velvet leaf40 ABUTH Chinese hemp velvet leaf
CHEAL Weißer Gänsefuß lamb's quarters (goosefoot)CHEAL white goose foot lamb's quarters (goosefoot)
IPOSS Prunkwindearten morning gloryIPOSS morning glory
SOLNI Schwarzer Nachtschatten black nightshadeSOLNI black nightshade
POLPE Flohknöterich lady's thumbPOLPE Knotweed lady's thumb
45 ECHCG Hühnerhirse barnyard grass SINAL Weißer Senf white mustard45 ECHCG millet barnyard grass SINAL white mustard
PHBPU Purpurtrichterwinde co mon morninggloryPHBPU purple funnel winch co mon morningglory
Tabelle 1 Herbizide Aktivität bei Nachauflaufanwendung im Ge- wächshaus (Beispiel-Verbindung Nr .4 )Table 1 Herbicidal activity in post-emergence use in the greenhouse (example compound no. 4)
Aufwandmenge 0,25 0,125 (kg/ha a. S.)Application rate 0.25 0.125 (kg / ha a.s.)
Testpflanzentest plants
ZEAMX 0 0 ABUTH 98 98ZEAMX 0 0 ABUTH 98 98
POLPE 98 98POLPE 98 98
IPOSS 98 95IPOSS 98 95
SOLNI 100 98SOLNI 100 98
Tabelle 2 Herbizide Aktivität bei Nachauflaufanwendung im Ge- wächshaus (Beispiel-Verbindung Nr. 10)Table 2 Post-emergence herbicidal activity in the greenhouse (example compound no. 10)
Aufwandmenge 0,5 0,25 (kg/ha a. S.)Application rate 0.5 0.25 (kg / ha a.s.)
Testpflanzen ECHCG 95 90Test plants ECHCG 95 90
ABUTH 98 98ABUTH 98 98
CHEAL 95 95CHEAL 95 95
IPOSS 90 90IPOSS 90 90
SOLNI 100 98SOLNI 100 98
Tabelle 3 Herbizide Aktivität bei Nachauflaufanwendung im Ge wächshaus (Beispiel Nr .1)Table 3 Herbicidal activity in post-emergence use in the greenhouse (Example No. 1)
Aufwandmenge 0,5 0,25 (kg/ha a. S.Application rate 0.5 0.25 (kg / ha a.s.
Testpflanzen ZEAMX 0 0 CHEAL 98 98 ECHCG 100 100 ABUTH 100 100 SINAL 100 100 SOLNI 100 100Test plants ZEAMX 0 0 CHEAL 98 98 ECHCG 100 100 ABUTH 100 100 SINAL 100 100 SOLNI 100 100
Die Verbindung aus Beispiel Nr. 14 zeigte bei Nachauflaufanwen- düng und Aufwandmengen von 0,5 kg/ha a.S. eine sehr gute herbizide Aktivität gegen POLPE, CHEAL und PHBPU sowie eine gute herbizide Aktivität gegen ABUTH. Bei Aufwandmengen von 0,25 kg/ha a.S. zeigte die Verbindung aus Beispiel 14 eine gute bis sehr gute herbizide Aktivität gegen ABUTH, POLPE, CHEAL und PHPBU. Bei beiden Aufwandmengen wurde eine hohe Selektivität gegenüber Weizen (TRZAS, keine Schädigung) beobachtet. Die Verbindung aus Beispiel 23 zeigte bei Nachauflaufanwendung und Aufwandmengen von 0,25 bzw. 0,5 Kg/ha a.S. eine sehr gute herbizide Aktivität gegen ABUTH, CHEAL und POLPE sowie eine gute Aktivität gegen ECHCG bei gleichzeitig hoher Selektivität gegen- über Weizen (TRZAS). 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 ).

Claims

Patentansprüche claims
1. Cyclohexenon-Derivate von bicyclischen Benzoesäuren der allgemeinen Formel I,1. cyclohexenone derivatives of bicyclic benzoic acids of the general formula I,
Figure imgf000077_0001
Figure imgf000077_0001
worinwherein
X für 0 , S , SO , S02 , N-R1 oder N-NR1R17 steht ,X represents 0, S, SO, S0 2 , NR 1 or N-NR 1 R 17 ,
R1 Wasserstof f , C1-C6-Alkyl , C1-C6-Halogenalkyl , C1-C6-Alkoxy, C1-C6-Halogenalkoxy, C1-C6-Alkylsulf onyl , C1-C6-Halogenalkylsulf onyl , C1-C6-Alkoxy-C1-C6-alkyl , C1-C6-Alkylcarbonyl , C1-C6-Halogenalkylcarbonyl , C1-C6-Alkylcarbonyl-C1-C6-alkyl , C1-C6-Alkylcarbonyl-C1-C6-alkylcarbonyl , C1-C6-Alkylcarbonyloxy-C1-C6-alkyl ,R 1 hydrogen f, 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 -haloalkylsulfonyl, 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,
C3-C6-Cycloalkyl , C3-C6-Cycloalkoxy ,C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkoxy,
C3-C6-Cycloalkylcarbonyl , C3-C6-Cycloalkyl-C1-C6-alkyl , C3-C6-Cycloalkoxy-C1-C6-alkyl ,C 3 -C 6 cycloalkylcarbonyl, C 3 -C 6 cycloalkyl-C 1 -C 6 alkyl, C 3 -C 6 cycloalkoxy-C 1 -C 6 alkyl,
C3-Cg-Cycloalkylcarbonyl-C1-C6 -alkyl ,C 3 -Cg cycloalkylcarbonyl-C 1 -C 6 alkyl,
C3-C6-Cycloalkoxycarbonyl-C1-C6-alkyl ,C 3 -C 6 cycloalkoxycarbonyl-C 1 -C 6 alkyl,
Cs-Cg-Cycloalkylcarbonyloxy-C1-C6-alkyl ,Cs-Cg-cycloalkylcarbonyloxy-C 1 -C 6 alkyl,
C3-C6-Cycloalkylsulf onyl ,C 3 -C 6 cycloalkylsulfonyl,
Phenyl , Phenylsulfonyl , Phenylcarbonyl ,Phenyl, phenylsulfonyl, phenylcarbonyl,
Phenyl-C1-C6-alkyl , Phenyl-C1-C6-alkylcarbonyl ,Phenyl-C 1 -C 6 -alkyl, phenyl-C 1 -C 6 -alkylcarbonyl,
Phenoxy-C1-C6-alkyl , Phenylcarbonyl-C1-C6-alkyl ,Phenoxy-C 1 -C 6 alkyl, phenylcarbonyl-C 1 -C 6 alkyl,
Phenoxycarbonyl-C1-C6-alkyl , oder Phenylcarbonyloxy-C1-C6-alkyl bedeuten ,Are phenoxycarbonyl-C 1 -C 6 -alkyl or phenylcarbonyloxy-C 1 -C 6 -alkyl,
Heterocyclyl , Heterocyclylsulfonyl , Heterocyclylcarbonyl , Heterocyclyl-C1-C6-alkyl , Heterocyclylcarbonyl-C1-C6-alkyl oder Heterocyclylcarbonyloxy-C1-C6-alkyl bedeuten , wobei die Phenyl-, Heterocyclyl- und Cycloalkylreste der vorgenannten Gruppen gegebenenfalls eine, zwei, drei oder vier Substituenten ausgewählt unter C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy, C1-C4-Alkylcarbonyl, C1-C4-Halogenalkylcarbonyl, C1-C4-Alkylsulfonyl, C1-C4-Halogenalkylsulfonyl, Nitro, Hydroxy oder Cyano tragen und/oder teilweise oder vollständig halogeniert sein können;Are heterocyclyl, heterocyclylsulfonyl, heterocyclylcarbonyl, heterocyclyl-C 1 -C 6 -alkyl, heterocyclylcarbonyl-C 1 -C 6 -alkyl or heterocyclylcarbonyloxy-C 1 -C 6 -alkyl, where the phenyl, heterocyclyl and cycloalkyl radicals of the abovementioned groups are 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 haloalkylsulfonyl, nitro, hydroxy or cyano and / or partially or completely halogenated could be;
R2 Halogen, C1-C6-Alkylthio, C1-C6-Halogenalkylthio, C1-C6-Alkylsulfinyl, C1-C6-Halogenalkylsulfinyl, C1-C6-Alkylsulfonyl oder C1-C6-Halogenalkylsulfonyl ;R 2 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;
R3 für Wasserstoff , Halogen, C1-C6-Alkyl oder C1-C6-Halogenalkyl , undR 3 represents hydrogen, halogen, C 1 -C 6 alkyl or C 1 -C 6 haloalkyl, and
Hex für substituiertes ( 3-Oxo-l-cyclohexen-2-yl)carbonyl der Formel Ha oder für substituiertesHex for substituted (3-oxo-l-cyclohexen-2-yl) carbonyl of the formula Ha or for substituted
( 1 , 3-Dioxo-2-cyclohexyl)methyliden der Formel Ilb(1,3-Dioxo-2-cyclohexyl) methylidene of the formula IIb
Figure imgf000078_0001
stehen, wobei die Variablen R4 bis R10 folgende Bedeutung haben:
Figure imgf000078_0001
stand, whereby the variables R 4 to R 10 have the following meaning:
R4 Hydroxy, Mercapto, Halogen, OR11, SR11, SOR12, S02R12, OS02R12, P(0)R13R14, OP(0)R13R14, P(S)R13R14, OP(S)R13R14' NR15R16, ONR15R16 oder N-gebundenes Heterocyclyl, das partiell oder vollständig halogeniert sein kann und/oder einen, zwei oder drei der folgenden Reste tragen kann: Nitro, Cyano, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy oder C1-C4-Halogenalkoxy;R 4 hydroxy, mercapto, halogen, OR 11 , SR 11 , SOR 12 , S0 2 R 12 , OS0 2 R 12 , P (0) R 13 R 14 , OP (0) R 13 R 14 , P (S) R 13 R 14 , OP (S) R 13 R 14 'NR 15 R 16 , ONR 15 R 16 or N-linked heterocyclyl, which 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 or C 1 -C 4 haloalkoxy;
R5, R9 unabhängig voneinander Wasserstoff, C1-C4-Alkyl oder C1-C4-Alkoxycarbonyl ;R 5 , R 9 independently of one another are hydrogen, C 1 -C 4 -alkyl or C 1 -C 4 -alkoxycarbonyl;
R6, R8, R10 unabhängig voneinander Wasserstoff oder C1-C4 -Alkyl ; R7 Wasserstoff, Halogen, Hydroxy, C1-C6-Alkyl, C1-C6-Halogenalkyl, Di- (C1-C6-alkoxy) -methyl, (C1-C6-Alkoxy)-(C1-C6-alkylthio) -methyl, Di- (C1-C6-alkylthio)methyl, C1-C6-Alkoxy , C1-C6-Halogenalkoxy, C1-C6-Alkylthio, C1-C6-Halogenalkylthio, C1-C6-Alkylsulfinyl, C1-C6-Halogenalkylsulfinyl, C1-C6-Alkylsulfonyl, C1-C6-Halogenalkylsulfonyl , C1-C6-Alkoxycarbonyl , C1-C6-Halogenalkoxycarbonyl ;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;
1 , 3-Dioxolan-2-yl, 1 , 3-Dioxan-2-yl,1,3-dioxolan-2-yl, 1,3-dioxan-2-yl,
1 , 3-Oxathiolan-2-yl, 1,3 Oxathian-2-yl ,1, 3-oxathiolan-2-yl, 1,3 oxathian-2-yl,
1, 3-Dithiolan-2-yl oder 1, 3-Dithian-2-yl, wobei die sechs letztgenannten Reste durch einen bis drei C1-C4-Alkylreste substituiert sein können; oder1, 3-dithiolan-2-yl or 1, 3-dithian-2-yl, it being possible for the six latter radicals to be substituted by one to three C 1 -C 4 -alkyl radicals; or
R6 und R8 oder R8 und R10 bilden gemeinsam eine π-Bindung oder eine C1-C5-Alkylkette, die einen zwei oder drei Reste aus folgender Gruppe tragen kann: Halogen, Cyano, C1-C4-Alkyl, C1-C4-Halogenalkyl oder C1-C4-Alkoxy- carbonyl; oderR 6 and R 8 or R 8 and R 10 together form a π bond or a C 1 -C 5 alkyl chain which can carry two or 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
R6 und R10 bilden gemeinsam eine C1-C4-Alkylkette, die einen zwei oder drei Reste aus folgender Gruppe tragen kann: Halogen, Cyano, C1-C4-Alkyl, C1-C4-Halogenalkyl oder C1-C4-Alkoxycarbonyl; oderR 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
R7 und R8 bilden gemeinsam eine -O-(CH2)p-O-, -O- (CH2 )p-S- ,R 7 and R 8 together form an -O- (CH 2 ) p -O-, -O- (CH 2 ) p -S-,
-S-(CH2)p-S-, -O-(CH2)q- oder -S- (CH2 )q-Kette , worin p für 2, 3, 4 oder 5 und q für 2, 3, 4, 5 oder 6 stehen, und die durch einen, zwei oder drei Reste aus folgender Gruppe substituiert sein kann: Halogen, Cyano, C1-C4-Alkyl, C1-C4-Halogenalkyl oder C1-C4-Alkoxycarbonyl; oder-S- (CH 2 ) p -S-, -O- (CH 2 ) q - or -S- (CH 2 ) q chain, in which p is 2, 3, 4 or 5 and q is 2, 3, 4, 5 or 6, and which can be substituted by one, two or 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
R7 und R8 bilden gemeinsam mit dem Kohlenstoff, an dem sie gebunden sind, eine Carbonylgruppe;R 7 and R 8 together with the carbon to which they are attached form a carbonyl group;
und worin die Variablen R11 bis R17 die folgenden Bedeutungen haben:and in which the variables R 11 to R 17 have the following meanings:
R11 C3-C6-Alkyl, C3-C6-Alkenyl, C3-C6-Halogenalkenyl,R 11 is C 3 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl,
C3-C6-Alkinyl, C3-C6-Halogenalkinyl, C3-C6-Cycloalkyl, C1-C6-Alkylcarbonyl , C2-C6-Alkenylcarbonyl , C2-C6-Alkinylcarbonyl, C3-C6-Cycloalkylcarbonyl, C1-C6-Alkoxycarbonyl , C3-C6-Alkenyloxycarbonyl , C3-C6-Alkinylox l, C1-C6-Alkylthiocarbonyl, C1-C6-Alkylaminocarbonyl, C3-C6-Alkenylaminocarbonyl, C3-C6-Alkinylaminocarbonyl , , N-Di ( C1-C6-alkyl ) aminocarbonyl , N- ( C3-C6-Alkenyl ) -N- ( C1-C6-alkyl ) -aminocarbonyl , N- ( C3-C6-Alkinyl ) -N- ( C1-C6-alkyl ) -aminocarbonyl ,C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkylcarbonyl, C 2 -C 6 alkenylcarbonyl, C 2 -C 6 alkynylcarbonyl, C 3 -C 6 cycloalkylcarbonyl, C 1 -C 6 alkoxycarbonyl, C 3 -C 6 alkenyloxycarbonyl, C 3 -C 6 alkynyloxy, C 1 -C 6 alkylthiocarbonyl, C 1 -C 6 alkylaminocarbonyl, C 3 -C 6 alkenylaminocarbonyl, C 3 -C 6 alkynylaminocarbonyl,, N-di (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- (C1-C6-Alkoxy)-N-(C1-C6-alkyl) -aminocarbonyl, N- ( C3-C6-Alkenyl) -N- (C1-C6-alkoxy) -aminocarbonyl, N- (C3-C6-Alkinyl ) -N- ( C1-C6-alkoxy) -aminocarbonyl , Di- (C1-C6-alkyl) -aminothiocarbonyl, C1-C6-Alkoxyimino-C1-C6-alkyl, wobei die genanntenN- (C 1 -C 6 alkoxy) -N- (C 1 -C 6 alkyl) aminocarbonyl, N- (C 3 -C 6 alkenyl) -N- (C 1 -C 6 alkoxy) - aminocarbonyl, N- (C 3 -C 6 alkynyl) -N- (C 1 -C 6 alkoxy) aminocarbonyl, di- (C 1 -C 6 alkyl) aminothiocarbonyl, C 1 -C 6 alkoxyimino- C 1 -C 6 alkyl, the aforementioned
Alkyl-, Cycloalkyl- oder Alkoxyreste partiell oder vollständig halogeniert sein können und/oder eine, zwei oder drei der folgenden Gruppen tragen können: Cyano, C1-C4-Alkoxy, C1-C4-Alkylthio, Di- (C1-C4-alkyl) amino, C1-C4-Alkylcarbonyl , C1-C4-Alkoxycarbonyl , C1-C4-Alkoxy-C1-C4-alkoxycarbonyl , Hydroxycarbonyl , C1-C4-Alkylaminocarbonyl , Di- (C1-C4-Alkyl) aminocarbonyl, Aminocarbonyl, C1-C4-Alkylcarbonyloxy oder C3-C6-Cycloalkyl,Alkyl, cycloalkyl or alkoxy radicals 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 alkylthio, di- (C 1 -C 4 alkyl) amino, C 1 -C 4 alkylcarbonyl, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkoxy-C 1 -C 4 alkoxycarbonyl, hydroxycarbonyl, C 1 -C 4 alkylaminocarbonyl, Di (C 1 -C 4 alkyl) aminocarbonyl, aminocarbonyl, C 1 -C 4 alkylcarbonyloxy or C 3 -C 6 cycloalkyl,
Phenyl, Phenyl-C1-C6-alkyl,Phenyl, phenyl-C 1 -C 6 -alkyl,
Phenylcarbonyl-C1-C6-alkyl , Phenylcarbonyl , Phenoxycarbonyl , Phenoxythiocarbonyl , Phenylaminocarbonyl,Phenylcarbonyl-C 1 -C 6 -alkyl, phenylcarbonyl, phenoxycarbonyl, phenoxythiocarbonyl, phenylaminocarbonyl,
N- ( C1-C6-Alkyl ) -N-phenylaminocarbonyl , Phenyl-C2-C6-alkenylcarbonyl, Heterocyclyl, Heterocyclyl-C1-C6-alkyl , Heterocyclylcarbonyl-C1-C6-alkyl, Heterocyclylcarbonyl, Heterocyclyloxycarbonyl,N- (C 1 -C 6 alkyl) -N-phenylaminocarbonyl, phenyl-C 2 -C 6 -alkenylcarbonyl, heterocyclyl, heterocyclyl-C 1 -C 6 -alkyl, heterocyclylcarbonyl-C 1 -C 6 -alkyl, heterocyclylcarbonyl, heterocyclyloxycarbonyl,
Heterocyclyloxythiocarbonyl , Heterocyclylaminocarbonyl ,Heterocyclyloxythiocarbonyl, heterocyclylaminocarbonyl,
N-(C1-C6-Alkyl) -N-heterocyclylaminocarbonyl oder He- terocyclyl-C2-Cg-alkenylcarbonyl, wobei der Phenyl- oder der Heterocyclyl-Rest der 18 letztgenanntenN- (C 1 -C 6 -alkyl) -N-heterocyclylaminocarbonyl or heterocyclyl-C 2 -Cg-alkenylcarbonyl, the phenyl or heterocyclyl radical of the 18 latter
Substituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy oder C1-C4-Halogenalkoxy;Substituents can be partially or completely halogenated and / or can carry one to 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;
R12 C1-C6-Alkyl, C3-C6-Alkenyl, C3-C6-Alkinyl oderR 12 is C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl or
C3-C6-Cycloalkyl, wobei die vier genannten Reste partiell oder vollständig halogeniert sein können und/ oder eine, zwei oder drei der folgenden Gruppen tragen können: Cyano, C1-C4-Alkoxy, C1-C4-Halogenalkoxy, C1-C4-Alkyl hio, logenalkylthio, C1-C4-Alkylcarbonyl, C1-C4-Alkoxycarbonyl oder C1-C4-Halogenalkoxycarbonyl ,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 alkyl hio, logenalkylthio, C 1 -C 4 alkylcarbonyl, C 1 -C 4 alkoxycarbonyl or C 1 -C 4 haloalkoxycarbonyl,
Phenyl, Phenyl-C1-C4-alkyl, Heterocyclyl oder Hetero- cyclyl-C1-C4-alkyl, wobei der Phenyl- oder der Hete- rocyclylrest der vier letztgenannten Substituenten partiell oder vollständig halogeniert sein kann und/ oder einen, zwei oder drei der folgenden Reste tragen kann: Nitro, Cyano, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy oderPhenyl, phenyl-C 1 -C 4 -alkyl, heterocyclyl or heterocyclic-C 1 -C 4 -alkyl, where the phenyl or heterocyclyl radical of the four last-mentioned substituents can be partially or completely halogenated and / or one, can carry 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
Cx-C4-AIkoxycarbony1;Cx-C 4 alkoxycarbony1;
R13, R14 unabhängig voneinander Wasserstoff, Hydroxy, C1-C6-Alkyl, C1-C6-Alkoxy, C1-C6-Alkylthio, Phenyl, Phenyl-C1-C4-alkyl oder Phenoxy, wobei die drei letztgenannten Substituenten partiell oder vollständig halogeniert sein können und/oder einen, zwei oder drei der folgenden Reste tragen können: Nitro, Cyano, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy, C1-C4-Halogenalkoxy oder C1-C4-Alkoxycarbonyl;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;
R15 Wasserstoff, C1-C6-Alkyl, C3-C6-Alkenyl,R 15 is hydrogen, C 1 -C 6 alkyl, C 3 -C 6 alkenyl,
C3-C6-Halogenalkenyl , C3-C6-Alkinyl ,C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl,
C3-C6-Halogenalkinyl , C3-C6-Cycloalkyl , C1-C6-Alkylcarbonyl, Hydroxy, C1-C6-Alkoxy,C 3 -C 6 haloalkynyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkylcarbonyl, hydroxy, C 1 -C 6 alkoxy,
C3-C6-Alkenyloxy, C3-C6-Alkinyloxy, Amino, C1-C6-Alkylamino, Di- (C1-C6-alkyl) amino oder C1-C6-Alkylcarbonylamino, wobei die genannten Alkyl-, Cycloalkyl- oder Alkoxyreste partiell oder vollständig halogeniert sein können und/oder einen, zwei oder drei der folgenden Reste tragen können: Cyano, C1-C4-Alkoxycarbonyl, C1-C4-Alkylaminocarbonyl , Di- (C1-C4-alkyl) aminocarbonyl oder C3-C6-Cycloalkyl,C 3 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy, amino, C 1 -C 6 alkylamino, di (C 1 -C 6 alkyl) amino or C 1 -C 6 alkylcarbonylamino, where the said Alkyl, cycloalkyl or alkoxy radicals can be partially or completely halogenated and / or can carry one, two or 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,
Phenyl, Phenyl-C1-C4-alkyl , Phenylcarbonyl, Heterocyclyl, Heterocycly-C1-C4-alkyl oder Heterocyclylcarbonyl, wobei der Phenyl- oder Heterocyclyl-Rest der sechs letztgenannten Substituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy oder C1-C4-Halogenalkoxy; R16,R17 unabhängig voneinander Wasserstoff, C1-C6-Alkyl, C3-C6-Alkenyl oder C3-C6-Alkinyl;Phenyl, phenyl-C 1 -C 4 -alkyl, phenylcarbonyl, heterocyclyl, heterocycly-C 1 -C 4 -alkyl or heterocyclylcarbonyl, where the phenyl or heterocyclyl radical of the six latter substituents can be partially or completely halogenated and / or one can carry up to 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; 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;
sowie deren landwirtschaftlich brauchbaren Salze.and their agriculturally useful salts.
2. Cyclohexenonderivate nach Anspruch 1, worin R2 in Formel I für Halogen, C1-C4-Alkylsulfonyl oder C1-C4-Halogenalkylsulfo- nyl steht.2. Cyclohexenone derivatives according to claim 1, wherein R 2 in formula I is halogen, C 1 -C 4 alkylsulfonyl or C 1 -C 4 haloalkylsulfonyl.
3. Cyclohexenonderivate nach einem der vorhergehenden Ansprüche, worin X in Formel I für N-R1 steht, worin3. Cyclohexenone derivatives according to one of the preceding claims, wherein X in formula I is NR 1 , wherein
R1 C1-C4-Alkyl, C1-C4-Alkoxy, C3-C6-Cycloalkyl , C1-C4-Alkyl- sulfonyl, Phenyl, Phenyl-C1-C4-alkyl oder Phenylsulfonyl bedeutet, wobei der Phenylring der drei letztgenannten Gruppen in der 4-Position mit Halogen oder C1-C4-Alkyl substituiert sein kann.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 , wherein the phenyl ring of the latter three groups in the 4-position can be substituted with halogen or C 1 -C 4 alkyl.
4. Cyclohexenonderivate nach einem der Ansprüche 1 bis 3, worin X in Formel I für N-NRiR17 steht, worin4. Cyclohexenone derivatives according to any one of claims 1 to 3, wherein X in formula I is N-NRiR 17 , wherein
R1 C1-C4-Alkyl, C1-C4-Alkoxy, C3-C6-Cycloalkyl , C1-C4-Alkyl- sulfonyl, Phenyl, Phenyl-C1-C4-alkyl oder Phenylsulfonyl, wobei der Phenylring der drei letztgenannten Gruppen in der 4-Position mit Halogen oder C1-C4-Alkyl substituiert sein kann, undR 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, wherein the phenyl ring of the last three groups can be substituted in the 4-position with halogen or C 1 -C 4 alkyl, and
R17 Wasserstoff oder C1-C4-Alkyl bedeuten.R 17 is hydrogen or C 1 -C 4 alkyl.
5. Cyclohexenonderivate nach einem der vorhergehenden Ansprüche, worin Hex in Formel I für einen Rest der Formel Ha steht, worin R4 ausgewählt ist unter Hydroxy, Mercapto, Halogen, OR11, SR11, S02R12, OS02R12, NR15R16 und gegebenenfalls substituiertes, N-gebundenes Heterocyclyl mit den für R11, R12, R15 und R16 in Anspruch 1 angegebenen Bedeutungen.5. cyclohexenone derivatives according to any one of the preceding claims, wherein hex in formula I is a radical of the formula Ha, wherein R 4 is selected from hydroxy, mercapto, halogen, OR 11 , SR 11 , S0 2 R 12 , OS0 2 R 12 , NR 15 R 16 and optionally substituted, N-linked heterocyclyl with the meanings given for R 11 , R 12 , R 15 and R 16 in claim 1.
6. Cyclohexenonderivate nach Anspruch 5, wobei in Formel I Hex für einen Rest Ha steht und6. Cyclohexenone derivatives according to claim 5, wherein in formula I hex represents a radical Ha and
R4 ausgewählt ist unter Hydroxy, C1-C4-Alkylcarbonyloxy, C1-C4-Alkylamino, Di-C1-C4-Alkylamino, C1-C4-Alkyl-thio, N-(C1-C4-Alkyloxy)-N-(C1-C4-alkyl) amino, C1-C4-Alkylsulfonyloxy, Phenylthio, Phenylsulfonyl, Phenylsulfonyloxy und N-gebundenem Heterocyclyl, wobei die Phenylgruppe und die Heterocyclylgruppe der vier letztge- nannten Substituenten mit Halogen, Nitro, Cyano oder C1-C4-Alkyl substituiert sein kann.R 4 is selected from 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 1 -C 4 alkylsulfonyloxy, phenylthio, phenylsulfonyl, phenylsulfonyloxy and N-linked heterocyclyl, the phenyl group and the heterocyclyl group of the four last- mentioned substituents can be substituted with halogen, nitro, cyano or C 1 -C 4 alkyl.
7. Cyclohexenonderivate nach einem der vorhergehenden Ansprüche, worin in Formel Ha oder Ilb7. Cyclohexenone derivatives according to one of the preceding claims, wherein in the formula Ha or Ilb
R5, R6 , R7 , R8, R9 und R10 unabhängig voneinander für Wasserstoff oder C1-C4-Alkyl stehen,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,
R7 auch für Hydroxy, C1-C4-Alkoxy, C1-C4-Alkylthio, Halogenalkoxy oder Halogenalkylthio stehen kann, oderR 7 can also represent hydroxy, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, haloalkoxy or haloalkylthio, or
R7 und R8 zusammen mit dem Kohlenstoffatom, an das sie gebunden sind auch eine Carbonylgruppe, einen 1,3-Dioxo- lan-, 1 , 3-Dithiolan-, 1 , 3-0xothiolan-, 1 , 3-Oxothian-,R 7 and R 8 together with the carbon atom to which they are attached also form a carbonyl group, a 1,3-dioxolane, 1, 3-dithiolane, 1, 3-0xothiolane, 1, 3-oxothiane,
1 , 3-Dithiolan- oder einen 1 , 3-Dithian-Ring bedeuten können, wobei die 2-Position der sechs genannten Ringe mit dem C-Atom identisch ist, an das R11 und R12 gebunden sind,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,
R5 und R9 oder R6 und R10 auch eine C1-C4-Alkylenkette bedeuten können, oderR 5 and R 9 or R 6 and R 10 can also mean a C 1 -C 4 alkylene chain, or
R6 und R8 oder R8 und R9 gemeinsam eine π-Bindung ausbilden können.R 6 and R 8 or R 8 and R 9 together can form a π bond.
8. Bicyclische Benzoesäuren der allgemeinen Formel IVa8. Bicyclic benzoic acids of the general formula IVa
Figure imgf000083_0001
Figure imgf000083_0001
worin X, R2 und R3 die in Anspruch 1 angegebenen Bedeutungen aufweisen.wherein X, R 2 and R 3 have the meanings given in claim 1.
9. Mittel, enthaltend mindestens ein Cyclohexenon-Derivat der Formel I oder ein landwirtschaftlich brauchbares Salz von I gemäß einem der Ansprüche 1 bis 7, und übliche Hilfsmittel.9. Agent containing at least one cyclohexenone derivative of the formula I or an agriculturally useful salt of I according to any one of claims 1 to 7, and conventional auxiliaries.
10. Verfahren zur Bekämpfung von unerwünschtem Pflanzenwuchs, dadurch gekennzeichnet, daß man eine herbizid wirksame Menge mindestens eines Cyclohe rivates der Formel I oder eines landwirtschaftlich brauchbaren Salzes von I gemäß einem der Ansprüche 1 bis 7, auf Pflanzen, deren Lebensraum und/ oder auf Samen einwirken läßt.10. A method for controlling unwanted vegetation, characterized in that a herbicidally effective amount of at least one Cyclohe rivates of the formula I or of an agriculturally useful salt of I according to one of claims 1 to 7, on plants, their habitat and / or on seeds.
11. Verwendung von Cyclohexenon-Derivaten der Formel I oder deren landwirtschaftlich brauchbaren Salzen gemäß einem der Ansprüche 1 bis 7 als Herbizide. 11. Use of cyclohexenone derivatives of the formula I or their agriculturally useful salts according to one of claims 1 to 7 as herbicides.
PCT/EP2000/005790 1999-06-25 2000-06-23 Cyclohexenone derivatives of bicyclic benzoic acids as herbicides WO2001000607A1 (en)

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DE19929259.0 1999-06-25
DE1999129259 DE19929259A1 (en) 1999-06-25 1999-06-25 New cyclohexanone derivatives of bicyclic benzoic acids useful as herbicides

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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 (en) * 1987-03-19 1988-09-21 Zeneca Limited Herbicidal substituted cyclic diones
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 (en) * 1995-08-25 1997-03-06 E.I. Du Pont De Nemours And Company Bicyclic herbicides
WO1997009324A1 (en) * 1995-09-01 1997-03-13 Basf Aktiengesellschaft 2-cyclohexane-1,3-dione benzoyl derivatives

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 (en) * 1987-03-19 1988-09-21 Zeneca Limited Herbicidal substituted cyclic diones
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 (en) * 1995-08-25 1997-03-06 E.I. Du Pont De Nemours And Company Bicyclic herbicides
WO1997009324A1 (en) * 1995-09-01 1997-03-13 Basf Aktiengesellschaft 2-cyclohexane-1,3-dione benzoyl derivatives

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DE19929259A1 (en) 2000-12-28

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