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WO2000059911A2 - Tricyclic cyclohexanedione derivatives - Google Patents

Tricyclic cyclohexanedione derivatives Download PDF

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Publication number
WO2000059911A2
WO2000059911A2 PCT/EP2000/002565 EP0002565W WO0059911A2 WO 2000059911 A2 WO2000059911 A2 WO 2000059911A2 EP 0002565 W EP0002565 W EP 0002565W WO 0059911 A2 WO0059911 A2 WO 0059911A2
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alkyl
alkoxy
halogen
cyano
hydrogen
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German (de)
French (fr)
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WO2000059911A3 (en
Inventor
Klaus Langemann
Ernst Baumann
Wolfgang Von Deyn
Steffen Kudis
Guido Mayer
Ulf Misslitz
Ulf Neidlein
Matthias Witschel
Thorsten Volk
Martina Otten
Karl-Otto Westphalen
Helmut Walter
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BASF SE
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BASF SE
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Publication of WO2000059911A3 publication Critical patent/WO2000059911A3/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Definitions

  • the present invention relates to new tricyclic cyclohexanedione derivatives with herbicidal activity, processes for the preparation of the tricyclic cyclohexanedione derivatives and intermediates for their preparation, compositions which contain them and the use of these derivatives or compositions comprising them for weed control.
  • Herbicidal tricyclic cyclohexanedione derivatives are known from the literature, for example from WO 97/19087.
  • the task was to find new tricyclic cyclohexanedione derivatives with improved properties.
  • R 1 is hydrogen, C ⁇ -C 6 -alkyl, C ⁇ -C 6 -haloalkyl,
  • R 2 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C ⁇ -C 6 -haloalkyl, C ⁇ -C 6 -haloalkoxy, optionally with C ⁇ -C 3 -alkyl, halogen, cyano, nitro or C ⁇ -C 3 alkyl- sulfonyl-substituted phenyl or phenylsulfonyl optionally substituted with C ⁇ -C-alkyl, halogen, cyano or nitro;
  • R 3 , R 4 are hydrogen, C -C 6 alkyl, C -C 6 haloalkyl,
  • R 5 is hydrogen or C -C alkyl
  • R 6 is hydrogen, C ⁇ -C ⁇ alkyl or halogen
  • R 7 is hydrogen or Cx-C 6 alkyl
  • R 8 is C ⁇ -C 6 alkyl or Cx -C 6 alkoxy
  • R 9 substituted (3-oxo-1-cyclohexen-2 -yl) carbonyl or substituted (1, 3-dioxo-2-cyclohexyl) methylidene;
  • herbicidal compositions which contain the compounds I and have a very good herbicidal action.
  • processes for the preparation of these compositions and processes for controlling unwanted vegetation using the compounds I have been found.
  • the 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, the alkaline earth metals, preferably calcium and magnesium, and the transition metals, preferably manganese, copper, zinc and iron, and ammonium, where one to four hydrogen atoms by C ⁇ - C 4 alkyl, hydroxy-C ⁇ -C4 alkyl, Cx-C4 alkoxy-C ⁇ -C 4 - lkyl, hydroxy-C ⁇ -C4-alkoxy-C ⁇ -C4 alkyl, substituted phenyl or benzyl can be, preferably ammonium, dirnethylammonium, diisopropylammonium, tetramethylammonium, tetrabutylammonium, 2 - (2-hydroxyeth-1-oxy) eth-1-ylammonium, di (2-hydroxyeth-1-yl) ammonium, tri-methylbenzylammonium , further phosphonium ions, s
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of C ⁇ -C 4 -alkanoic acids, preferably formate, Acetate, propionate and butyrate.
  • Heterocyclyl which can be partially or completely halogenated and / or can carry one to three of the following radicals: nitro, cyano, C ⁇ -C 4 alkyl, C ⁇ -C 4 haloalkyl, C ⁇ -C 4 alkoxy or C ⁇ - C 4 - haloalkoxy; Ri, R i5 hydrogen, C ⁇ -C 4 alkyl or C ⁇ -C 4 alkoxycarbonyl;
  • Ri 2 , R 14 , R 16 are hydrogen or C x -C 4 alkyl
  • R 3 is hydrogen, halogen, hydroxy, C ⁇ -C 6 alkyl
  • C ⁇ -C 6 -haloalkyl di- (C ⁇ -C 6 -alkoxy) -methyl, (C ⁇ -C ⁇ -alkoxy) - (C ⁇ -C 6 -alkylthio) -methyl, di- (C ⁇ -C 6 -alkylthio ) methyl, C ⁇ -C 6 alkoxy, C ⁇ -C 6 haloalkoxy, C ⁇ -C 6 alkylthio, C ⁇ -C 6 haloalkylthio, C ⁇ -C 6 alkylsulfinyl, C -C 6 haloalkylsulfinyl, C ⁇ -C 6 -alkylsulfonyl, C ⁇ -C 6 -haloalkyl-sulfonyl, C ⁇ -C ⁇ -alkoxycarbonyl, C ⁇ -C 6 -haloalkoxy-carbony1;
  • R 12 and R X3 or R 12 and R 16 together form a ⁇ bond or a C ⁇ -C 5 alkyl chain which can carry one to three radicals from the following group: halogen, cyano, C ⁇ -C 4 alkyl, C ⁇ - C 4 halo alkyl or C ⁇ -C 4 alkoxycarbonyl, from;
  • R i2 and R X6 together form a C ⁇ -C 4 alkyl chain which can carry one to three radicals from the following group: halogen, cyano, C ⁇ -C 4 alkyl, C ⁇ -C haloalkyl or C ⁇ -C 4 alkoxycarbonyl, out;
  • R X3 and R X4 together form a -0- (CH 2 ) p -0-, -O- (CH 2 ) P -S-, -S- (CH 2 ) P -S-, -0- (CH 2 ) g - or -S- (CH 2 ) q chain, which can be substituted by one to three radicals from the following group: halogen, cyano, C ⁇ -C 4 -alkyl, C ⁇ -C -haloalkyl or C ⁇ -C 4 - Alkoxycarbonyl;
  • R i3 and R i4 together with the carbon to which they are attached form a carbonyl group
  • R 17 C ⁇ -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 "haloalkynyl, C 3 -C 6 cycloalkyl,
  • C ⁇ -C 6 -alkoxyimino-C ⁇ -C 6 -alkyl where the alkyl, cycloalkyl or alkoxy radicals mentioned can be partially or completely halogenated and / or can carry one to three of the following groups: cyano, C ⁇ -C 4 alkoxy , C ⁇ -C 4 alkylthio, di- (C ⁇ -C 4 alkyl) amino,
  • C ⁇ -C 4 -alkylcarbonyl C ⁇ -C 4 -alkoxycarbonyl, C ⁇ -C -alkoxy-C ⁇ -C -alkoxycarbonyl, hydroxycarbonyl, C ⁇ -C 4 -alkylaminocarbonyl, di - (C x -C -alkyl) aminocarbonyl , Aminocarbonyl, C ⁇ -C 4 alkylcarbonyloxy or C 3 -C 6 cycloalkyl;
  • Heterocyclyl -C ⁇ -C 6 -alkenylcarbonyl where the phenyl or heterocyclyl radical of the 18 latter substituents can be partially or completely halogenated and / or can carry one to three of the following radicals: nitro, cyano, C ⁇ -C alkyl, C ⁇ -C 4 haloalkyl, C ⁇ -C 4 alkoxy or C ⁇ -C 4 haloalkoxy;
  • C 3 -C ⁇ cycloalkyl where the four radicals mentioned can be partially or completely halogenated and / or can carry one to three of the following groups: cyano, C ⁇ -C 4 alkoxy, C ⁇ -C 4 haloalkoxy, C ⁇ -C 4 alkylthio, C ⁇ -C 4 haloalkylthio, C ⁇ -C 4 alkylcarbonyl, C ⁇ -C alkoxycarbonyl or Cx -C 4 haloalkoxycarbonyl; Phenyl, phenyl-C -C -alkyl, heterocyclyl or heterocyclic-C C-C 4 -alkyl, where the phenyl or heterocyclyl radical of the four last-mentioned substituents can be partially or completely halogenated and / or one to three of the following Can carry leftovers:
  • Ri 9 , R 20 are hydrogen, hydroxy, C ⁇ -C 6 alkyl, C ⁇ -C 6 alkoxy, C ⁇ -C 6 alkylthio, phenyl, phenyl -C ⁇ -C alkyl or phenoxy, the three latter substituents being partially or completely may be halogenated and / or may carry one to three of the following radicals: nitro, cyano, C ⁇ -C4-alkyl, C ⁇ -C4 halo-alkyl, C ⁇ -C4-alkoxy, C ⁇ -C4-haloalkoxy or Cx -C alkoxycarbonyl;
  • R 21 is hydrogen, C ⁇ -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C & haloalkynyl, C 3 -C 6 -Cycloalkyl, C ⁇ -C 6 alkylcarbonyl, hydroxy, C ⁇ -C 6 alkoxy, C 3 -C 6 alkenyloxy, C 3 -C ⁇ alkynyloxy, amino, C ⁇ -C 6 alkylamino, di- (C ⁇ -C ⁇ - lkyl) amino or C ⁇ -C ⁇ alkylcarbonylamino, 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 ⁇ -C 4 alkoxycarbonyl , C ⁇ -C -alkylaminocarbonyl, di-
  • R 22 hydrogen f, C ⁇ - C 6 alkyl, C 3 -C 6 alkenyl or
  • Ha also represents the tautomeric forms Ha ', Ha''andHa''',
  • Ilb also represent the tautomeric forms Ilb ', Ilb''andIlb'''.
  • C ⁇ -C-alkyl and the alkyl parts of phenyl -C ⁇ -C 4 -alkyl and heterocyclyl -C ⁇ -C 4 -alkyl: for example methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl or 1 , 1-dimethylethyl;
  • C ⁇ -C 6 alkyl and the alkyl parts of C ⁇ -C6-alkoxyimino-C ⁇ -C 6 - alkyl, N-C ⁇ -C 6 -alkoxy-N-C ⁇ -C 6 -alkylamino, N (C ⁇ -C 6 -alk - oxy) -N- (C ⁇ -C 6 ⁇ alkyl) -aminocarbonyl, N- (C 3 -C 6 -alkenyl) -N- (C ⁇ -C 6 -alkyl) -aminocarbonyl, (C 3 -C 6 -Alkynyl) -N- (C ⁇ -C 6 ⁇ alkyl) -aminocarbonyl, N- (C ⁇ -C 6 -alkyl) -N-phenyla-minocarbonyl, N- (C ⁇ -C 6 -alkyl) -N-heterocyclylaminocarbonyl , Phenyl-
  • C ⁇ -C 4 -haloalkyl a C ⁇ -C-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
  • C ⁇ -C 6 -haloalkyl and the haloalkyl parts of N-C ⁇ -C 6 -haloalkylamino: C ⁇ -C 4 -haloalkyl, as mentioned above, and for example 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl, undecafluoropentyl , 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl or dodecafluorohexyl;
  • C ⁇ -C 4 alkoxy for example methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1, 1-dimethylethoxy;
  • N-C ⁇ -C 6 -alkoxy and the alkoxy parts of N-C ⁇ -C 6 -alkoxyamino, di- (C ⁇ -C 6 -alkoxy) methyl, (C ⁇ -C 6 -alkoxy) (C ⁇ -C 6 -alkylthio) - methyl , C ⁇ -C 6 -alkoxyimino-C ⁇ -C 6 -alkyl, N-C ⁇ -C 6 -alkoxy- N-C ⁇ -C 6 -alkylamino, N- (C ⁇ -C 6 ⁇ alkoxy) -N- (C ⁇ -C 6- alkyl) -amino-carbonyl, N- (C 3 -C 6 -alkenyl) -N- (C ⁇ -C 6 -alkoxy) -aminocarbonyl and N- (C 3 -C 6 -alkynyl) -N- (C ⁇ -C 6 -alkoxy) -amin
  • C ⁇ -C ⁇ -haloalkoxy C ⁇ -C 4 -haloalkoxy, as mentioned above, and for example 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorhexoxy, 6-chlorohexoxy, 6- Bromhexoxy, 6-iodohexoxy or dodecafluorohexoxy;
  • C ⁇ -C 4 alkylthio for example methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio or 1, 1-dimethylethylthio;
  • C ⁇ -C 6 -alkoxy C ⁇ -C ⁇ - alkylthio methyl: C ⁇ -C -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-methylpentylthio, 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,
  • C ⁇ -C 4 haloalkylthio a C ⁇ -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-tri- chloroethylthio, 2-chloro-2-fluoroethylthio,
  • C ⁇ -C 6 -haloalkylthio C ⁇ -C 4 -haloalkylthio, as mentioned above, and for example 5-fluoropentylthio, 5-chloropentylthio, 5-bromopentylthio, 5-iodopentylthio, undecafluoropentylthio, 6-fluorhexylthio, 6-chlorohexylthio, 6-bromohexylthio, 6-iodohexylthio or dodecafluorohexylthio;
  • C ⁇ -C 4 -haloalkylsulfinyl C ⁇ -C 4 ⁇ alkylsulfinyl, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example fluoromethylsulfinyl, difluoromethylsulfinyl, trifluoromethylsulfinyl, chlorodifluoromethylsulfinyl, bromodifluoromethylsulfinyl , 2-fluoroethylsulfinyl, 2-chloroethylsulfinyl, 2-bromoethylsulfinyl, 2-iodoethylsulfinyl, 2, 2-difluoroethylsulfinyl, 2, 2, 2-trifluoroethylsulfinyl, 2, 2, 2-trichloroethylsulfinyl,
  • 2-chloro-2-fluoroethylsulfinyl 2-chloro-2, 2-difluoroethylsulfinyl - nyl, 2, 2-dichloro-2-fluoroethylsulfinyl, pentafluoroethylsulfinyl nyl, 2-fluoropropylsulfinyl, 3-fluoropropylsulfinyl, 2-chloropropylsulfinyl, 3-chloropropylsulfinyl, 2-bromopropylsulfinyl, 3-bromopropylsulfinyl, 2, 2-difluoropropylsulfinyl, 2, 3-difluoropropylsulfinyl, 2, 3, 3-dichloromethyl 3-trifluoropropylsulfinyl, 3, 3, 3-trichloropropylsulfinyl, 2, 2, 3, 3, 3-
  • C ⁇ -C 6 -haloalkylsulfinyl C ⁇ -C 4 -haloalkylsulfinyl as mentioned above, as well as 5-fluoropentylsulfinyl, 5-chloropentylsulfinyl, 5-bromopen-ylsulfinyl, 5-iodopentylsulfinyl, undecafluoropentylsulfinyl, 6-fluorohexylsulfinyl, 6-chlorosulfinyl 6-bromohexyls finyl, 6-iodohexylsulfinyl or dodecafluorohexylsulfinyl;
  • C ⁇ -C 4 haloalkylsulfonyl a C ⁇ -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, chlorodifluoromethyldifluoromethyl, 2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl, 2, 2-difluoroethylsulfonyl, 2, 2, 2-trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl, 2-chloro-2, 2-difluoroethylsulfon
  • C ⁇ -C 6 -haloalkylsulfonyl C ⁇ -C -haloalkylsulfonyl as mentioned above, and 5-fluoropentylsulfonyl, 5-chloropentylsulfonyl, 5-bromopentylsulfonyl, 5-iodopentylsulfonyl, 6-fluorohexylsulfonyl, 6-bromhexylsulfonylylylsulfonyl;
  • C ⁇ -C 6 -alkylamino for example methylamino, ethylamino, propylamino, 1-methylethylamino, butylamino, 1-methylpropylamino, 2-methylpropylamino, 1, 1-dimethylethylamino, pentylamino,
  • Di- (C ⁇ -C 4 -alkyl) amino for example N, N-dimethylamino, N, N-diethylamino, 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, 1-dimethylethyl) amino, N-ethyl-N -methylamino, N-methyl-N-propylamino, N-methyl-N- (1-methylethyl) amino, N-butyl-N-methylamino, N-methyl-N- (1-methylpropyl) amino, N -Methyl-N- (2-methyl-propyl) amino, N- (1, 1-dimethylethyl) -N-methylamino, N-ethyl-N
  • Di- (C ⁇ -C 6 -alkyl) amino Di- (C ⁇ -C -alkyl) amino as mentioned above, and N, N-dipentylamino, N, N-dihexylamino, N-methyl-N-pentylamino, N-ethyl -N-pentylamino, N-methyl -N-hexylamino or N-ethyl-N-hexylamino.
  • C ⁇ -C 4 alkylcarbonyl for example methylcarbonyl, ethylcarbonyl, propylcarbonyl, 1-methylethylcarbonyl, butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl or 1, 1-dimethylethylcarbonyl;
  • C ⁇ -C 6 _ alkylcarbonyl C ⁇ -C 4 alkylcarbonyl, as mentioned above, and for example pentylcarbonyl, 1-methylbutylcarbonyl, 2-methylbutylcarbonyl, 3-methylbutylcarbonyl, 2,2-dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, hexylcarbonyl,
  • C ⁇ -C 4 haloalkylcarbonyl a C ⁇ -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, dichlorofluoracetyl, chlorodifluoroacetyl, 2-fluoroethylcarbonyl, 2-chloroethylcarbonyl, 2-bromoethylcarbonyl, 2-iodoethylcarbonyl, 2, 2-difluoroethylcarbonyl, 2,2, 2-trifluoroethylcarbonyl, 2-chloro-2-fluoroethylcarbonyl, 2- Chloro-2, 2-difluoroe
  • C ⁇ -C 6 -haloalkylcarbonyl a C ⁇ -C 4 -haloalkylcarbonyl radical as mentioned above, and 5-fluoropentylcarbonyl, 5-chloropentylcarbonyl, 5 -bromopentylcarbonyl, perfluoropentylcarbonyl, 6-fluorhexylcarbonyl, 6 -chlorohexylcarbonyl, 6-bromo- hexylcarbonyl or perfluorohexylcarbonyl;
  • C ⁇ -C 4 -alkoxycarbonyl and the alkoxycarbonyl parts of di- (C ⁇ -C 4 -alkyl) amino-C ⁇ -C 4 -alkoxycarbonyl, i.e. for example methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, 1-methylethoxycarbonyl, butoxycarbonyl, 1- Methylpropoxycarbonyl, 2-methylpropoxycarbonyl or 1, 1-dimethylethoxycarbonyl;
  • (C ⁇ -C 6 ⁇ alkoxy) carbonyl (C ⁇ -C 4 -alkoxy) carbonyl, as mentioned above, and for example pentoxycarbonyl, 1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 2, 2-dimethyl-propoxycarbonyl, 1- Ethylpropoxycarbonyl, Hexoxycarbonyl, 1, 1-Dirnethylpropoxycarbonyl, 1, 2-Dimethylpropoxycarbonyl, 1-Methylpentoxycarbonyl, 2-Methylpentoxycarbonyl, 3-Methyl-pentoxycarbonyl, 4-Methylpentoxycarbonyl, 1, 1-Dimethylbutoxycarbonyl, 1,2-Dimethylbutoxycarbonony1, 1 3-dimethylbutoxycarbonyl, 2, 2-dimethylbutoxycarbonyl, 2, 3-dimethylbutoxycarbonyl, 3, 3-dimethylbutoxycarbonyl, 1-ethylbutoxycarbonyl, 2-eth
  • C ⁇ -C 4 haloalkoxycarbonyl a C ⁇ -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, bromodifluoryl, bromodifluoro 2-fluoroethoxycarbonyl, 2-chloroethoxycarbonyl, 2-bromoethoxycarbonyl, 2-iodoethoxycarbonyl, 2, 2-difluoroethoxycarbonyl, 2,2, 2-trifluoroethoxycarbonyl, 2-chloro-2-fluoroethoxycarbonyl, 2-chloro-2, 2-difluoroethoxycarbonyl, 2,2-dichloro-2-fluoroethoxycarbonyl, 2,2,2-trichloroethoxycarbony
  • Cx-Cg-halooxycarbonyl a C ⁇ -C 4 halooxycarbonyl radical as mentioned above, and 5-fluoropentoxycarbonyl, 5-chloropentoxycarbonyl, 5-bromopentoxycarbonyl, 6-fluorohexoxycarbonyl, 6-chlorohexoxycarbonyl or 6-bromhexoxycarbonyl;
  • (C ⁇ -C 4 alkyl) carbonyloxy acetyloxy, ethylcarbonyloxy, propylcarbonyloxy, 1-methylethylcarbonyloxy, butylcarbonyloxy, 1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy or 1, 1-dimethylethylcarbonyloxy;
  • (C ⁇ -C 4 -alkylamino) carbonyl for example methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl, 1-methylethylaminocarbonyl, butylaminocarbonyl, 1-methylpropylaminocarbonyl, 2-methylpropylaminocarbonyl or 1, 1-dimethylethylaminocarbonyl;
  • (C ⁇ -C 6 -alkylamino) carbonyl (C ⁇ -C 4 -alkylamino) carbonyl, as mentioned above, and for example pentylaminocarbonyl, 1-methylbutylaminocarbonyl, 2-methylbutylaminocarbonyl, 3-methylbutylaminocarbonyl, 2, 2-dimethylpropylaminocarbonyl, 1-ethyl-propylaminocarbonyl, hexylaminocarbonyl, 1, 1-dimethylpropylaaminocarbonyl, 1, 2-dimethylpropylaminocarbonyl, 1-methylpentylaminocarbonyl, 2-methylpentylaminocarbonyl, 3-methylpentylaminocarbonyl, 4-methylpentylaminocarbonyl, 1, 1-dimethyl 1, 2-dimethylbutylaminocarbonyl, 1,3-dimethylbutylaminocarbonyl, 2, 2-dimethylbutylaminocarbonyl,
  • Di- (C ⁇ -C 4 -alkyl) -aminocarbonyl for example N, N-dimethylaminocarbonyl, N, N-diethylaminocarbonyl, N, N-di- (1-methylethyl) aminocarbonyl, N, N-dipropylaminocarbonyl, N, N -Dibutylaminocarbonyl, N, N-di- (1-methylpropyl) -aminocarbonyl, N, N-di- (2-methylpropyl) -aminocarbonyl, N, N-di- (1, 1-dimethylethyl) -aminocarbonyl, N -Ethyl-N-methylaminocarbonyl, N-methyl-N-propyla-minocarbonyl, N-methyl-N- (1-methylethyl) -aminocarbonyl, N-butyl-N-methylaminocarbonyl, N-methyl-N
  • Di- (C ⁇ -C 6 ⁇ alkyl) -aminocarbonyl Di- (C ⁇ -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-dimethyl-propyl) -aminocarbonyl, N- Methyl-N- (1-ethyl-propyl) -aminocarbonyl, N-methyl-N-hexylaminocarbonyl, N-methyl-N- (1, 1-dimethylpropyl) -aminocarbonyl, N-methyl-N-N-
  • Di- (C ⁇ -C 6 -alkyl) -aminothiocarbonyl e.g. N, N-dimethylamino-thiocarbonyl, N, N-diethylaminothiocarbonyl, N, N-di- (1-methylethyl) aminothiocarbonyl, N, N-dipropylaminothiocarbonyl, N, N -Dibutylaminothiocarbonyl, N, N-di- (1-methylpropyl) -amino-thiocarbonyl, N, N-di- (2-methylpropyl) -aminothiocarbonyl,
  • C ⁇ -C 4 -alkoxy-C ⁇ -C 4 -alkoxy C ⁇ -C 4 -alkoxy, and the alkoxyalkoxy parts of C ⁇ -C 4 -alkoxy-C ⁇ -C 4 -alkoxycarbonyl: C ⁇ -C 4 -alkoxy, as mentioned above, substituted C ⁇ -C 4 - Alkoxy, for example for Methoxymethoxy, ethoxymethoxy, propoxymethoxy, (1-methylethoxy) methoxy, butoxymethoxy, (l-methylpropoxy) methoxy, (2-methylpropoxy) methoxy, (1, 1-dimethylethoxy) methoxy, 2- (methoxy) ethoxy, 2- ( Ethoxy) ethoxy, 2- (propoxy) ethoxy, 2- (1-methylethoxy) ethoxy, 2- (butoxy) ethoxy, 2- (l-methylpropoxy) ethoxy, 2- (2-methylpropoxy) ethoxy, 2- ( 1,
  • C 3 -C 6 alkenyl and the alkenyl parts of C 3 -C 6 alkenylcarbonyl, C 3 -C 6 alkenyloxy, C 3 -C 6 alkenyloxycarbonyl, C 3 -C 6 alkenylaminocarbonyl, N- (C 3 -C 6 -Alkenyl) -N- (C ⁇ -C 6 ) alkylaminocarbonyl, N- (C 3 -C 6 -alkenyl) -N- (C ⁇ -C 6 -alkoxy) aminocarbonyl: eg prop-2-ene -l-yl, but-l-en-4-yl, 1-methyl-prop-2-en-l-yl, 2-methyl-prop-2-en-l-yl, 2-butene-l-yl , l-penten-3-yl, l-penten-4-yl, 2-penten-4-yl, 1-methyl-but-2-en-l-yl, 2-
  • 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-trichlorallyl, 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;
  • C 3 -C 6 alkynyl and the alkynyl parts of C 3 -Cg alkynylcarbonyl, C 3 -C 6 alkynyloxy, C 3 -C 6 alkynyloxycarbonyl, C 3 -C 6 alkynylaminocarbonyl, N- ( C 3 -C 6 alkynyl) -N- (C ⁇ -C 6 - alkyl) aminocarbonyl, N- (C 3 -C 6 -alkynyl) -N- (C ⁇ -C6 alkoxy aminocarbonyl: for example, propargyl, but- l-in-3-yl, but-l-in-4-yl, but-2-in-l-yl, pent-l-in-3-yl, pent-l-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
  • 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, for example 1,1-difluoroprop-2- in-l-yl, 3-iodo-prop-2-in-l-yl, 4-fluorobut-2-in-l-yl, 4-chlorobut-2-in-l-yl, 1, 1-difluorobut- 2-in-l-yl, 4-iodobut-3-in-l-yl, 5-fluoropent-3-in-l-yl, 5-iodo-pent-4-in-l-yl, 6- Fluoro-hex-4-in-1-yl or 6-iodo-hex-5-in-1-yl;
  • 6-link rings such as:
  • a bicyclic ring system can be formed with a fused-on phenyl ring or with a C 3 -C 6 carbocycle or with a further 5- to 6-membered heterocycle.
  • N-linked heterocyclyl a saturated, partially saturated or unsaturated 5- or 6-membered N-linked heterocyclic ring, the at least one nitrogen and optionally one to three identical or different hetero atoms, selected from the following group: oxygen, sulfur or nitrogen contains, e.g.
  • N-linked 5-membered rings such as: Tetrahydropyrrol-1-yl, 2,3-dihydro-lH-pyrrol-l-yl, 2,5-di-hydro-lH-pyrrol-1-yl, pyrrol-1-yl, tetrahydropyrazol-1-yl, tetrahydroisoxazole 2-yl, tetrahydroisothiazol-2-yl, tetrahydroimidazol-1-yl, tetrahydrooxazol-3-yl, tetrahydrothiazol-3-yl, 4,5-dihydro-lH-pyrazol-l-yl, 2,5- Dihydro-lH-pyrazol-l-yl, 2,3-dihydro-lH-pyrazol-l-yl, 2,5-dihydroisoxazol-2-yl, 2,3-dihydroisoxazol-2-yl, 2,5- Di
  • N-linked 6-membered rings such as:
  • Piperidin-1-yl 1, 2, 3, 4-tetrahydropyridin-l-yl, 1,2,5,6-tetrahydropyridin-1-yl, 1, 4-dihydropyridin-l-yl, 1,2- Dihydropyridin-1-yl, hexahydropyrimidin-1-yl, hexahydropyrazin-1-yl, hexahydropyridazin-1-yl, tetrahydro-1, 3-oxazin-3-yl, tetrahydro-1, 3-thiazin-3- yl, tetrahydro-1, 4-thiazin-4-yl, tetrahydro-1, 4-oxazin-4-yl, tetrahydro-1, 2-oxazin-2-yl, 2H-5,6-dihydro 1, 2-oxazin-2-yl, 2H-5, 6-dihydro-l, 2-thiazin-2-yl, 2H-3, 6-dihydr
  • Phthalimide tetrahydrophthalimide, succinimide, maleimide or glutarimide
  • Tricyclic cyclohexanedione derivatives of the formula III are preferred
  • Tricyclic cyclohexanedione derivatives of the formula IV are also preferred
  • the variables preferably have the following meanings, in each case individually or in combination: Ri is hydrogen, C ⁇ -C 6 -alkyl, C ⁇ -C 6 -haloalkyl,
  • R 2 is hydrogen, C ⁇ -C 6 alkyl, C ⁇ -C 6 alkoxy, C ⁇ -C 6 haloalkyl, C ⁇ -C ⁇ -haloalkoxy, optionally with C terrorism dilemma-C 3 alkyl, halogen, cyano, nitro or C ⁇ -C 3 alkyl sulfonyl substituted phenyl or phenyl sulfonyl optionally substituted with C ⁇ -C 3 alkyl, halogen, cyano or nitro;
  • R 3 , R 4 are hydrogen, C ⁇ -C 6 -alkyl, C ⁇ -C 6 -alkoxy, C ⁇ -C 6 -alkylthio, C ⁇ -C 6 -alkylsulfonyl, C 2 -C 6 -alkoxyalkyl, C ⁇ -C 6 -alkoxycarbonyl, C ⁇ -C ⁇ alkylcarbonyl, halogen, optionally with C ⁇ -C 3 alkyl, halogen, cyano or
  • R 5 is hydrogen
  • R 6 is hydrogen, C ⁇ -C 3 alkyl or halogen
  • N-linked heterocyclyl which can be partially or completely halogenated and / or can carry one to three of the following radicals: nitro, cyano, C ⁇ .C 4 alkyl, C ⁇ -C 4 haloalkyl, C ⁇ -C 4 alkoxy or C ⁇ -C 4 haloalkoxy; preferably hydroxy, mercapto, halogen, OR i "7 , SR i7 , S0 2 R i8 , OS0 2 R i8 , NR 2i R 22 , ONR 18 R i8 or N-linked heterocyclyl, which can be partially or completely halogenated and / or can carry one to three of the following radicals: nitro, cyano, C ⁇ -C 4 alkyl,
  • Ri, Ri 5 is hydrogen or C ⁇ -C 4 alkyl, such as methyl, ethyl or propyl; preferably hydrogen or methyl;
  • R i2 , R 4 , R i6 hydrogen or C ⁇ -C 4 alkyl, such as methyl, ethyl or propyl; preferably hydrogen or methyl;
  • R 3 is hydrogen, hydroxy, C ⁇ -C6-alkyl, di- (C ⁇ -C 6 -alk-oxy) -methyl, (C ⁇ -Ce -alkoxy) - (C ⁇ -C 6 -alkylthio) -methyl, di- (C ⁇ -C 6 -alkylthio) methyl, C ⁇ -C 6 alkylthio, Cx-C6 -Halogenalky1thio, C-C6 alkylsulfinyl, C ⁇ -C 6 "haloalkylsulfinyl, alkylsulfonyl or C ⁇ -C ⁇
  • Radicals can be substituted by one to three C ⁇ -C 4 alkyl radicals
  • R i2 and R 13 or R 12 and R i6 together form a ⁇ bond or a C 3 -C 5 alkyl chain which have up to three residues from the following
  • Group can carry: halogen, cyano, C ⁇ -C 4 alkyl, C ⁇ -C 4 haloalkyl or C ⁇ -C 4 alkoxycarbonyl, from;
  • Ri 2 and R 16 together form a C ⁇ -C 4 alkyl chain which can carry one to three radicals from the following group: halogen, cyano, C ⁇ -C 4 alkyl, C ⁇ -C 4 haloalkyl or C ⁇ -C 4 alkoxycarbonyl , out;
  • R 3 and Rl 4 together form a -0- (CH 2 ) p -0-, -0- (CH 2 ) p -S- or -S- (CH 2 ) P -S chain, which by one to three Residues from the following group can be substituted: halogen, cyano, C ⁇ -C 4 alkyl, C ⁇ -C 4 haloalkyl or C ⁇ - ⁇ alkoxycarbonyl; preferably R 13 and R i4 together form a -O- (CH) p -0-, -0- (CH 2 ) p -S- or -S- (CH 2 ) p -S chain, which is represented by one to three the radicals from the following groups can be substituted: Cx-C 4 haloalkyl or C ⁇ -C 4 alkoxycarbonyl;
  • R i3 and R i4 together with the carbon to which they are attached form a carbonyl group; C ⁇ -C ⁇ alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl,
  • C ⁇ -C 6 alkyl preferably C ⁇ -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C ⁇ -C 6 alkylcarbonyl, C ⁇ -C 6 alkoxycarbonyl, C ⁇ -C 6 alkylaminocarbonyl or N, N-di (C ⁇ -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 ⁇ -C 4 alkoxy, C ⁇ -C 4 alkylthio or C ⁇ -C 4 alkoxycarbonyl;
  • R 18 is C ⁇ -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 ⁇ -C 4 alkoxy, C ⁇ -C 4 alkylthio, C ⁇ -C alkylcarbonyl or C ⁇ -C 4 alkoxycarbonyl;
  • R i9 , R 20 hydroxy, C ⁇ -C 6 alkyl, C ⁇ -C 6 alkoxy, phenyl, phenyl -C ⁇ -C 4 alkyl or phenoxy, where the latter three substituents can be partially or completely halogenated and / or can carry one to three of the following radicals: nitro, cyano, C ⁇ -C 4 -alkyl, Cx -C 4 -haloalkyl, C ⁇ -C -alkoxy, C ⁇ -C 4 -haloalkoxy or Cx-C 4 -alkoxycarbonyl;
  • R 2i C ⁇ -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl,
  • Di- (C ⁇ -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 ⁇ -C -alkoxycarbonyl, C ⁇ -C 4 alkylaminocarbonyl, di- (C ⁇ -C 4 alkyl) aminocarbonyl or C 3 -C 6 cycloalkyl;
  • R 22 is C ⁇ -C ⁇ alkyl or C 3 -C 6 alkenyl
  • R is methyl, ethyl, halogen, methoxy, methylthio, methylsulfonyl, nitro, cyano;
  • R 2 is methyl, ethyl, optionally with halogen, cyano,
  • R 3 , R 4 are hydrogen, C ⁇ -C 6 -alkyl, C ⁇ -C 6 -alkylcarbonyl, phenyl optionally substituted by halogen, cyano, nitro,
  • R 5 is hydrogen
  • R 6 is hydrogen, methyl, chlorine
  • R i ° halogen OR i7 , SR 17 , S0 2 R l8 , OS0 2 R i8 , NR 2i R 22 , ONR l8 Ri 8 or N-linked heterocyclyl, which can be partially or completely halogenated and / or one to three of the can carry the following radicals: nitro, cyano, C ⁇ -C 4 alkyl, C ⁇ -C haloalkyl, C ⁇ -C alkoxy or C ⁇ -C 4 haloalkoxy;
  • R i5 hydrogen or C ⁇ -C 4 alkyl
  • R 12 , R i , R 6 are hydrogen or Cx-C 4 alkyl
  • R i3 hydrogen, hydroxy, C ⁇ -C 6 -alkyl, di - (C ⁇ -C 6 -alk-oxy) -methyl, (C ⁇ -C 6 -alkoxy) - (C ⁇ -C 6 -alkylthio) -methyl, di- (C ⁇ -C 6 alkylthio) methyl, C ⁇ -C 6 alkylthio,
  • Ri and R i6 together form a C ⁇ -C 4 alkyl chain which can carry one to three radicals from the following group: halogen, C ⁇ -C 4 alkyl or c ⁇ -C 4 haloalkyl;
  • R i2 and R 16 together form a methylene bridge which can carry one or two radicals from the following group: halogen, C ⁇ -C 2 alkyl or C ⁇ -C 2 haloalkyl;
  • R 13 and R i4 together with the carbon to which they are attached form a carbonyl group
  • the compounds of the formula Ia are also extremely preferred.
  • Li stands for a nucleophilically displaceable leaving group, such as halogen, for example bromine or chlorine, hetaryl, for example imidazolyl or pyridyl, carboxylate, for example acetate or trifluoroacetate etc.
  • halogen for example bromine or chlorine
  • hetaryl for example imidazolyl or pyridyl
  • carboxylate for example acetate or trifluoroacetate etc.
  • the activated benzoic acid Va can be used directly, as in the case of the benzoyl halides, or generated in situ, e.g. with dicyclohexylcarbodiimide, triphenylphosphine / azodicarboxylic acid ester, 2-pyridine disulfide / triphenylphosphine, carbonyldiimidazole etc.
  • auxiliary base it may be advantageous to carry out the acylation reaction in the presence of a base.
  • the reactants and the auxiliary base are expediently used in equimolar amounts.
  • a slight excess of the auxiliary base e.g. Under certain circumstances, 1.2 to 1.5 molar equivalents, based on Va or Vb, can be advantageous.
  • Suitable auxiliary bases are tertiary alkylammes, pyridine or alkali metal carbonates.
  • 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 become.
  • benzoyl halides are used as the activated carboxylic acid component, it may be expedient to cool the reaction mixture to 0-10 ° C. when this reactant is added. The mixture is then stirred at 20-100 ° C., preferably at 25-50 ° C., until the reaction is complete. The 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 the 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.
  • a solvent 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.
  • 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 mole percent, based on the ester. Preferably acetone cyanohydrin or trimethylsilyl cyanide, e.g. in an amount of 5 to 15, preferably about 10 mole percent, 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.
  • 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. B. chlorine or bromine, hetaryl, e.g. B. imidazolyl, carboxylate, e.g. B. acetate, or sulfonate, e.g. B. mesylate or triflate etc.
  • halogen for. B. chlorine or bromine
  • hetaryl e.g. B. imidazolyl
  • carboxylate e.g. B. acetate
  • sulfonate e.g. B. mesylate or triflate etc.
  • the compounds of formula A ⁇ , Aß, A ⁇ or A ⁇ can be used directly, such as. B. in the case of carboxylic acid halides or generated in situ, for. B. 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 compounds of the formula V are prepared by oxidation of the compounds of the formula XIII using oxidizing agents:
  • T is C ⁇ -C -alkoxy and the other substituents have the meaning described above.
  • Suitable oxidizing agents are, for example, m-chloroperbenzoic acid, peroxyacetic acid or hydrogen peroxide, if appropriate in the presence of a catalyst such as tungsten.
  • Compounds of the formula Xllla are prepared by dipolar cycloaddition of compounds of the formula XIV in the presence of an oxidizing agent (see, for example, Kim, JN et.al. Synth. Commun. 1990, 20, 1373; Hassner, A. et. Al. Synthesis 1989, 57; Kellabennani, AE et al. Tetrahedron 1995, 51, 10923),
  • T is C ⁇ -C -alkoxy and the other substituents have the meanings described above.
  • oxidizing agents come e.g. Chloramine T or sodium hypochlorite are used.
  • T is C ⁇ -C 4 alkoxy and the other substituents have the meaning described above.
  • the oximes XIV are prepared using generally known methods from the aldehydes XVI (see March, J. Advanced Organic Chemistry, 4th Ed., Wiley and Sons 1992, pp. 906 ff.).
  • T is C ⁇ -C -alkoxy and the other substituents have the meaning described above.
  • the hydrazone XV is represented by generally known methods from the aldehydes XVI (see March, J. Advanced Organic Chemistry, 4th Ed., Wiley, 1992, pp. 904 ff.).
  • T is C ⁇ -C 4 alkoxy and the other substituents have the meaning described above.
  • Compounds of the formula XVI are prepared by nucleophilic aromatic substitution of compounds of the formula XVII with substituted allyl thiols in polar solvents in the presence of bases.
  • Tertiary amines such as triethylamine or pydridine or alkali metal carbonates such as lithium carbonate or sodium carbonate can be used as bases.
  • Methanol, ethanol, dimethylformamide or N-methyl-pyrrolidone are suitable as solvents.
  • aldehydes of the formula XVII are known from, for example, WO 98/31681.
  • Hydroxylammonium chloride (4.48 g, 64.5) is added to a solution of the methyl ester from stage a) (15.85 g, 58.6 mmol) and Na CO 3 (3.5 g, 33 mmol) in ethanol (200 ml) mmol) was added and the mixture was stirred at RT over the weekend. Water (200 ml) is added and the mixture is stirred for a further hour before the mixture is concentrated on a rotary evaporator. The residue is taken up in water / ethyl acetate, the organic phase is dried over Na 2 S0 4 and the solvent is removed. The oxime is obtained quantitatively as a light syrup.
  • step d) The acid from step d) (4.4 g, 16.3 mmol) was dissolved in 30 ml of glacial acetic acid and a spatula tip of sodium tungstate was added. Thereafter, perhydrol (4.16 g, 36.7 mmol) was added dropwise at 50 ° C. and the mixture was stirred at 50 ° C. for a further 4 h. The mixture was stirred into ice water and extracted with ethyl acetate. The organic phase was washed with water, dried over sodium sulfate and concentrated.
  • the compounds I and their agriculturally useful salts are suitable - both as isomer mixtures and in the form of the pure isomers - as herbicides.
  • the I-containing 1C herbicides control vegetation very well on nonculture areas, especially at high application rates. In crops such as wheat, rice, maize, soybeans and cotton, they work against weeds and grass weeds without causing any significant damage to crops. This effect occurs especially at low application rates.
  • the compounds I or compositions containing them can also be used in a further number of crop plants for eliminating undesired plants.
  • the following are considered
  • Triticum aestivum Triticum durum, Vicia faba, Vitis vinifera, Zea mays.
  • the compounds I can also be used in crops which are tolerant by breeding including genetic engineering methods the 5 action of herbicides are used.
  • the herbicidal compositions or the active compounds can be applied in the pre-emergence or in the post-emergence. If the active ingredients are less compatible for certain crop plants, application techniques can be used in which the herbicidal compositions are sprayed with the aid of sprayers in such a way that the leaves of the sensitive crop plants are not hit wherever possible, while the active ingredients are applied to the leaves of undesirable plants growing below them or the uncovered floor area (post-directed, lay-by).
  • the compounds I or the herbicidal compositions comprising them can be sprayed or atomized, for example in the form of directly sprayable aqueous solutions, powders, suspensions, including high-strength aqueous, oily or other suspensions or dispersions, emulsions, old-dispersions, pastes, dusts, sprays or granules , Dusting, scattering or pouring.
  • the application forms depend on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, alkylated benzenes or their derivatives, alcohols such as methanol, ethanol, propanol, butanol, cyclohexanol, ketones such as cyclohexanone or strongly polar solvents, e.g. B. amines such as N-methylpyrrolidone or water.
  • mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives
  • Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water.
  • the tricyclic cyclohexanedione derivatives as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers.
  • concentrates consisting of an active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil, which are suitable for dilution with water.
  • the surface-active substances are the alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic acids, for example lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa- , Hepta and octadecanols and fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl or nonylphenol, alkylphenyl, arylphenyl,
  • Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
  • Granules e.g. Coated, impregnated and homogeneous granules can be produced by binding the active ingredients to solid carriers.
  • Solid carriers are mineral earths such as silica, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, Ammonium nitrate, ureas and vegetable products such as corn flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
  • mineral earths such as silica, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium s
  • the concentrations of the active ingredients I in the ready-to-use preparations can be varied over a wide range.
  • the formulations generally contain 0.001 to 98% by weight, preferably 0.01 to 95% by weight, of at least one active ingredient.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).
  • the compounds I according to the invention can be formulated, for example, as follows:
  • I 20 parts by weight of compound no. 49.1 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.
  • VIII 1 part by weight of compound 49.1 is dissolved in a mixture consisting of 80 parts by weight of cyclohexanone and 20
  • Wettol ® EM 31 non-ionic emulsifier based on ethoxylated castor oil. A stable emulsion concentrate is obtained.
  • the tricyclic cyclohexanedione derivatives can be mixed with numerous representatives of other herbicidal or growth-regulating active compound groups and applied together.
  • the active compound application rates are 0.001 to 3.0, preferably 0.01 to 1.0 kg / ha of active substance (see also)
  • Plastic pots with loamy sand with about 3.0% humus served as the 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 clear plastic hoods until the plants had grown. This cover causes the test plants to germinate evenly, provided that this has not been impaired by the active ingredients.
  • test plants were first grown to a height of 3 to 15 cm, depending on the growth habit, and then treated with the active ingredients suspended or emulsified in water.
  • the test plants were either sown directly and grown in the same containers or they were first grown separately as seedlings and transplanted into the test containers a few days before the treatment.
  • the application rate for post-emergence treatment was 0.5 or 0.25 kg / ha a. S.
  • the plants were kept at temperatures of 10 - 25 ° C or 20 - 35 ° C depending on the species.
  • the trial period lasted 2 to 4 weeks. During this time, the plants were cared for and their response to each treatment was evaluated.
  • Evaluation was carried out on a scale from 0 to 100. 100 means no emergence of the plants or complete destruction of at least the aerial parts and 0 means no damage or normal growth.
  • the plants used in the greenhouse experiments are composed of the following types:

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Abstract

The invention relates to tricyclic cyclohexanedione derivatives of formula (I) in which the substituents have the following meaning: R1 is hydrogen, C¿1?-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, halogen, cyano or nitro; X is O or NR?2; R2¿ is hydrogen, C¿1?-C6 alkyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 haloalkoxy, phenyl that is optionally substituted with C1-C3 alkyl, halogen, cyano, nitro or C1-C3 alkylsulfonyl or phenylsulfonyl that is optionally substituted with C1-C3 alkyl, halogen, cyano or nitro; R?3, R4¿ is hydrogen, C¿1?-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, NR?7R8, C¿2-C6 alkoxyalkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylcarbonyl, halogen, cyano, nitro, phenyl that is optionally substituted with C1-C3 alkyl, halogen, cyano or nitro; R5 is hydrogen or C¿1?-C4 alkyl; R?6¿ is hydrogen, C¿1?-C6 alkyl or halogen; R?7¿ is hydrogen or C¿1?-C6 alkyl; R?8 is C¿1-C6 alkyl or C1-C6 alkoxy; 1 is 0, 1 or 2; n is 1 or 2; R9 is substituted (3-oxo-1-cyclohexene-2-yl)carbonyl or substituted (1,3-dioxo-2-cyclohexyl)methylidene. The invention also relates to the agriculturally useful salts of the compounds (I), to methods for producing said tricyclic cyclohexanedione derivatives and to the intermediates for their production. The invention encompasses agents containing the inventive compounds and the use of said derivatives or of agents containing them for weed control.

Description

Tricyclische CyclohexandionderivateTricyclic cyclohexanedione derivatives

Beschreibungdescription

Die vorliegende Erfindung betrifft neue tricyclische Cyclohexandionderivate mit herbizider Wirkung, Verfahren zur Herstellung der tricyclischen Cyclohexandionderivate sowie Zwischenprodukte zu deren Herstellung, Mittel, welche diese enthalten sowie die Verwendung dieser Derivate oder sie enthaltender Mittel zur Unkrautbekämpfung.The present invention relates to new tricyclic cyclohexanedione derivatives with herbicidal activity, processes for the preparation of the tricyclic cyclohexanedione derivatives and intermediates for their preparation, compositions which contain them and the use of these derivatives or compositions comprising them for weed control.

Aus der Literatur sind herbizidwirksame tricyclische Cyclohexandionderivate bekannt, beispielsweise aus WO 97/19087.Herbicidal tricyclic cyclohexanedione derivatives are known from the literature, for example from WO 97/19087.

Die herbiziden Eigenschaften der bekannten Verbindungen sowie die Verträglichkeit gegenüber Kulturpflanzen können jedoch nur bedingt befriedigen.However, the herbicidal properties of the known compounds and the compatibility with crop plants can only satisfy to a limited extent.

Die Aufgabe bestand darin neue tricyclische Cyclohexandionderivate mit verbesserten Eigenschaften zu finden.The task was to find new tricyclic cyclohexanedione derivatives with improved properties.

Es wurden nun neue tricyclische Cyclohexandionderivate der Formel I gefundenNew tricyclic cyclohexanedione derivatives of the formula I have now been found

Figure imgf000003_0001
Figure imgf000003_0001

wobei die Variablen folgende Bedeutung haben:where the variables have the following meaning:

R1 Wasserstoff, Cχ-C6-Alkyl, Cι-C6-Haloalkyl,R 1 is hydrogen, Cχ-C 6 -alkyl, Cι-C 6 -haloalkyl,

Cχ-C6-Alkoxy, Cι-C6-Haloalkoxy, Cι-C6 -Alkylthio, Cι-C6-Haloalkylthio, Cι-C6 -Alkylsulfinyl, Cχ-C6-Halo- alkylsulfinyl, Cχ-Cβ -Alkylsulfonyl, Cι-C6-Haloalkylsulfonyl, Halogen, Cyano- oder Nitro;Cχ-C 6 -alkoxy, Cι-C 6 -haloalkoxy, Cι-C 6 -alkylthio, Cι-C 6 -haloalkylthio, Cι-C 6 -alkylsulfinyl, Cχ-C 6 -haloalkylsulfinyl, Cχ-Cβ -alkylsulfonyl, -CC 6 haloalkylsulfonyl, halogen, cyano- or nitro;

X 0 oder NR2;X 0 or NR 2 ;

R2 Wasserstoff, Cι-C6-Alkyl, Cι-C6-Alkoxy, Cχ-C6-Halo- alkyl, Cχ-C6 -Haloalkoxy, gegebenenfalls mit Cχ-C3-Alkyl, Halogen, Cyano, Nitro oder Cχ-C3-Alkyl- sulfonyl substituiertes Phenyl oder gegebenenfalls mit Cχ-C -Alkyl, Halogen, Cyano oder Nitro substituiertes Phenylsulfonyl;R 2 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, Cχ-C 6 -haloalkyl, Cχ-C 6 -haloalkoxy, optionally with Cχ-C 3 -alkyl, halogen, cyano, nitro or Cχ -C 3 alkyl- sulfonyl-substituted phenyl or phenylsulfonyl optionally substituted with Cχ-C-alkyl, halogen, cyano or nitro;

R3, R4 Wasserstoff, C -C6-Alkyl, C -C6-Haloalkyl,R 3 , R 4 are hydrogen, C -C 6 alkyl, C -C 6 haloalkyl,

C -C6-Alkoxy, Cχ-Cδ -Haloalkoxy, Cχ-C6 -Alkylthio, Cχ-C6 -Haloalkylthio, Cχ-Cβ -Alkylsulfinyl, Cχ-C6-Halo- alkylsulfinyl, Cχ-C6 -Alkylsulfonyl, Cχ-C6-Haloalkylsulfonyl, NR7R8, C2-C6-Alkoxyalkyl, Cχ-C6 -Alkoxy- carbonyl, Cx-Cβ-Alkylcarbonyl, Halogen, Cyano, Nitro, gegebenenfalls mit Cχ-C3-Alkyl, Halogen, Cyano oder Nitro substituiertes Phenyl ,-C -C 6 alkoxy, Cχ-Cδ-haloalkoxy, Cχ-C 6 -alkylthio, Cχ-C 6 -haloalkylthio, Cχ-Cβ -alkylsulfinyl, Cχ-C 6 -haloalkylsulfinyl, Cχ-C 6 -alkylsulfonyl, Cχ -C 6 haloalkylsulfonyl, NR 7 R 8 , C 2 -C 6 alkoxyalkyl, Cχ-C 6 alkoxycarbonyl, Cx-Cβ-alkylcarbonyl, halogen, cyano, nitro, optionally with Cχ-C 3 alkyl, halogen , Cyano or nitro substituted phenyl,

R5 Wasserstoff oder C -C -Alkyl;R 5 is hydrogen or C -C alkyl;

R6 Wasserstoff, Cχ-Cδ -Alkyl oder Halogen;R 6 is hydrogen, Cχ-C δ alkyl or halogen;

R7 Wasserstoff oder Cx-C6-Alkyl;R 7 is hydrogen or Cx-C 6 alkyl;

R8 Cχ-C6 -Alkyl oder Cx -C6-Alkoxy;R 8 is Cχ-C 6 alkyl or Cx -C 6 alkoxy;

1 0, 1 oder 2;1 0, 1 or 2;

n 1 oder 2;n 1 or 2;

R9 substituiertes (3 -Oxo-1-cyclohexen-2 -yl) carbonyl oder substituiertes (1, 3 -Dioxo-2 -cyclohexyl) -methyliden;R 9 substituted (3-oxo-1-cyclohexen-2 -yl) carbonyl or substituted (1, 3-dioxo-2-cyclohexyl) methylidene;

sowie landwirtschaftlich brauchbare Salze der Verbindungen I.as well as agriculturally useful salts of the compounds I.

Ferner wurden herbizide Mittel gefunden, die die Verbindungen 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 Verbindungen I gefunden.Furthermore, herbicidal compositions have been found which contain the compounds I and have a very good herbicidal action. In addition, processes for the preparation of these compositions and processes for controlling unwanted vegetation using the compounds I have been found.

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.Salts of those cations or the acid addition salts of those acids whose cations, or anions, the do not adversely affect the herbicidal activity of the compounds I.

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 gewünschtenfalls ein bis vier Wasserstoffatome durch Cχ-C4-Alkyl, Hydroxy-Cχ-C4-alkyl, Cx -C4 -Alkoxy-Cχ-C4- lkyl, Hydro- xy-Cχ-C4-alkoxy-Cχ-C4-alkyl, Phenyl oder Benzyl ersetzt sein können, vorzugsweise Ammonium, Dirnethylammonium, Diisopropyl- ammonium, Tetramethylammonium, Tetrabutylammonium, 2 - (2-Hydroxy- eth-1-oxy) eth-1-ylammonium, Di (2 -hydroxyeth- 1-yl) ammonium, Tri - methylbenzylammonium, des weiteren Phosphoniumionen, Sulfonium- ionen, vorzugsweise Tri (Cχ-C4-alkyl) sulfonium und Sulfoxonium- ionen, vorzugsweise Tri (Cχ-C-alkyl) sulfoxonium, in Betracht.The cations used are in particular ions of the alkali metals, preferably lithium, sodium and potassium, the alkaline earth metals, preferably calcium and magnesium, and the transition metals, preferably manganese, copper, zinc and iron, and ammonium, where one to four hydrogen atoms by Cχ- C 4 alkyl, hydroxy-Cχ-C4 alkyl, Cx-C4 alkoxy-Cχ-C 4 - lkyl, hydroxy-Cχ-C4-alkoxy-Cχ-C4 alkyl, substituted phenyl or benzyl can be, preferably ammonium, dirnethylammonium, diisopropylammonium, tetramethylammonium, tetrabutylammonium, 2 - (2-hydroxyeth-1-oxy) eth-1-ylammonium, di (2-hydroxyeth-1-yl) ammonium, tri-methylbenzylammonium , further phosphonium ions, sulfonium ions, preferably tri (Cχ-C 4 -alkyl) sulfonium and sulfoxonium ions, preferably tri (Cχ-C-alkyl) sulfoxonium, into consideration.

Anionen von brauchbaren Säureadditionsalzen sind in erster Linie Chlorid, Bromid, Fluorid, Hydrogensulfat, Sulfat, Dihydrogen- phosphat, Hydrogenphosphat, Nitrat, Hydrogencarbonat, Carbonat, Hexafluorosilikat, Hexafluoro osphat, Benzoat sowie die Anionen von Cχ-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 Cχ-C 4 -alkanoic acids, preferably formate, Acetate, propionate and butyrate.

Hervorzuheben sind die erfindungsgemäßen Verbindungen der Formel I, wobei R9 für den Rest Ha oder IlbThe compounds of the formula I according to the invention are to be emphasized, where R 9 for the radical Ha or IIb

Figure imgf000005_0001
Figure imgf000005_0001

Ha IlbHa Ilb

steht, wobei die Variablen folgende Bedeutung haben:stands, whereby the variables have the following meaning:

Rl° Hydroxy, Mercapto, Halogen, ORl"7 , SRi"7 , SORi8, S02R18 ,Rl ° hydroxy, mercapto, halogen, OR l "7 , SR i" 7 , SOR i8 , S0 2 R 18 ,

OS02R18 , P (0) Rl9R20 , OP (0) R19R20 , P (S) R19R20 , OP (S) R19R20 ' NR21R22 , ONR18R18 oder N-gebundenesOS0 2 R 18 , P (0) R 19 R 20 , OP (0) R 19 R 20 , P (S) R 19 R 20 , OP (S) R 19 R 20 ' NR 21 R 22 , ONR 18 R 18 or N-linked

Heterocyclyl, das partiell oder vollständig haloge- niert sein kann und/oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, Cχ-C4 -Alkyl , Cχ -C4 -Halogenalkyl , Cχ -C4 -Alkoxy oder Cχ -C4 - Halogen - alkoxy; Ri , Ri5 Wasserstoff, Cχ-C4-Alkyl oder Cχ-C4-Alkoxycarbonyl;Heterocyclyl, which can be partially or completely halogenated and / or can carry one to three of the following radicals: nitro, cyano, Cχ-C 4 alkyl, Cχ -C 4 haloalkyl, Cχ -C 4 alkoxy or Cχ - C 4 - haloalkoxy; Ri, R i5 hydrogen, Cχ-C 4 alkyl or Cχ-C 4 alkoxycarbonyl;

Ri2, R14, R16 Wasserstoff oder Cx-C4-Alkyl;Ri 2 , R 14 , R 16 are hydrogen or C x -C 4 alkyl;

R3 Wasserstoff, Halogen, Hydroxy, Cχ-C6 -Alkyl,R 3 is hydrogen, halogen, hydroxy, Cχ-C 6 alkyl,

Cχ-C6-Halogenalkyl, Di- (Cχ-C6-alk- oxy) -methyl, (Cχ-Cδ -Alkoxy) - (Cχ-C6 -alkylthio) -methyl, Di- (Cχ-C6-alkylthio) methyl, Cχ-C6-Alkoxy, Cχ-C6-Halogenalkoxy, Cχ-C6 -Alkylthio, Cχ-C6 -Halogen- alkylthio, Cχ-C6 -Alkylsulfinyl, C -C6-Halogenalkyl- sulfinyl, Cχ-C6 -Alkylsulfonyl, Cχ-C6-Halogenalkyl- sulfonyl, Cχ-Cδ -Alkoxycarbonyl, Cχ-C6-Halogenalkoxy- carbony1;Cχ-C 6 -haloalkyl, di- (Cχ-C 6 -alkoxy) -methyl, (Cχ-Cδ -alkoxy) - (Cχ-C 6 -alkylthio) -methyl, di- (Cχ-C 6 -alkylthio ) methyl, Cχ-C 6 alkoxy, Cχ-C 6 haloalkoxy, Cχ-C 6 alkylthio, Cχ-C 6 haloalkylthio, Cχ-C 6 alkylsulfinyl, C -C 6 haloalkylsulfinyl, Cχ -C 6 -alkylsulfonyl, Cχ-C 6 -haloalkyl-sulfonyl, Cχ-C δ -alkoxycarbonyl, Cχ-C 6 -haloalkoxy-carbony1;

l,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 bis drei Cχ-C -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 last six radicals can be substituted by one to three Cχ-C-alkyl radicals;

oderor

R12 und RX3 oder R12 und R16 bilden gemeinsam eine π-Bindung oder eine Cχ-C5-Alkylkette, die einen bis drei Reste aus folgender Gruppe tragen kann: Halogen, Cyano, Cχ-C4-Alkyl, Cχ-C4 -Halogen- alkyl oder Cχ-C4 -Alkoxycarbonyl, aus;R 12 and R X3 or R 12 and R 16 together form a π bond or a Cχ-C 5 alkyl chain which can carry one to three radicals from the following group: halogen, cyano, Cχ-C 4 alkyl, Cχ- C 4 halo alkyl or Cχ-C 4 alkoxycarbonyl, from;

oderor

Ri2 und RX6 bilden gemeinsam eine Cχ-C4-Alkylkette, die einen bis drei Reste aus folgender Gruppe tragen kann: Halogen, Cyano, Cχ-C4 -Alkyl, Cχ-C -Halogenalkyl oder Cχ-C4 -Alkoxycarbonyl, aus;R i2 and R X6 together form a Cχ-C 4 alkyl chain which can carry one to three radicals from the following group: halogen, cyano, Cχ-C 4 alkyl, Cχ-C haloalkyl or Cχ-C 4 alkoxycarbonyl, out;

RX3 und RX4 bilden gemeinsam eine -0- (CH2)p-0- , -O- (CH2)P-S- , -S- (CH2)P-S- , -0-(CH2)g- oder -S- (CH2) q-Kette, die durch einen bis drei Reste aus folgender Gruppe substituiert sein kann: Halogen, Cyano, Cχ-C4 -Alkyl, Cχ-C -Halogenalkyl oder Cχ-C4 -Alkoxycarbonyl;R X3 and R X4 together form a -0- (CH 2 ) p -0-, -O- (CH 2 ) P -S-, -S- (CH 2 ) P -S-, -0- (CH 2 ) g - or -S- (CH 2 ) q chain, which can be substituted by one to three radicals from the following group: halogen, cyano, Cχ-C 4 -alkyl, Cχ-C -haloalkyl or Cχ-C 4 - Alkoxycarbonyl;

oderor

Ri3 und Ri4 bilden gemeinsam mit dem Kohlenstoff, an dem sie gebunden sind eine Carbonylgruppe aus;R i3 and R i4 together with the carbon to which they are attached form a carbonyl group;

R17 Cχ-C6 -Alkyl, C3-C6-Alkenyl, C3-C6-Halogenalkenyl, C3-C6-Alkinyl, C3-C6"Halogenalkinyl, C3-C6-Cycloalkyl,R 17 Cχ-C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 "haloalkynyl, C 3 -C 6 cycloalkyl,

Cχ-C6-Alkylcarbonyl, C2-C6-Alkenylcarbonyl, C2-C6-Al- kinyl carbonyl, C3-C6-Cycloalkyl carbonyl, Cχ-C6-Alk- oxycarbonyl, C3 -Cδ-Alkenyloxycarbonyl, C3 -C6-Alkiny1- oxycarbonyl, Cχ-C6-Alkylthiocarbonyl, Cχ-C6-Alkyl- aminocarbonyl , C3 -C6 -Alkenylaminocarbonyl , C3 -CÖ -Alkinylaminocarbony1 , N, N-Di (Cx -C6 -alkyl) amino- carbonyl, N- (C3-C6-Alkenyl) -N- (C -C6- alkyl) -amino- carbonyl, N- (C3-C6-Alkinyl) -N- (Cχ-C6 -alkyl) -amino- carbonyl, N- (Cχ-Cδ -Alkoxy) -N- (Cχ-C6-alkyl) -amino- carbonyl, N- (C3 -C6-Alkenyl) -N- (Cχ-C6- alkoxy) -amino- carbonyl, N- (C3 -C6 -Alkiny1) -N- (Cχ-C6-alkoxy) -amino- carbonyl, Di- (Cχ-C6-alkyl) -aminothiocarbonyl,Cχ-C 6 -alkylcarbonyl, C 2 -C 6 -alkenylcarbonyl, C 2 -C 6 -alkynylcarbonyl, C 3 -C 6 -cycloalkyl carbonyl, Cχ-C 6 -alk- oxycarbonyl, C 3 -C δ- alkenyloxycarbonyl, C 3 -C 6 -alkiny1- oxycarbonyl, Cχ-C 6 -alkylthiocarbonyl, Cχ-C 6 -alkyl-aminocarbonyl, C 3 -C 6 -alkenylaminocarbonyl, C 3 -C Ö - Alkynylaminocarbony1, N, N-di (Cx -C 6 alkyl) aminocarbonyl, N- (C 3 -C 6 alkenyl) -N- (C -C 6 alkyl) aminocarbonyl, N- (C 3 -C 6 -alkynyl) -N- (Cχ-C 6 -alkyl) -amino-carbonyl, N- (Cχ-C δ -alkoxy) -N- (Cχ-C 6 -alkyl) -amino-carbonyl, N - (C 3 -C 6 -Alkenyl) -N- (Cχ-C 6 -alkoxy) -amino-carbonyl, N- (C 3 -C 6 -alkiny1) -N- (Cχ-C 6 -alkoxy) -amino - carbonyl, di- (Cχ-C 6 -alkyl) -aminothiocarbonyl,

Cχ-C6-Alkoxyimino-Cχ-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, Cχ-C4 -Alkoxy, Cχ-C4 -Alkylthio, Di- (Cχ-C4- alkyl) amino,Cχ-C 6 -alkoxyimino-Cχ-C 6 -alkyl, where the alkyl, cycloalkyl or alkoxy radicals mentioned can be partially or completely halogenated and / or can carry one to three of the following groups: cyano, Cχ-C 4 alkoxy , Cχ-C 4 alkylthio, di- (Cχ-C 4 alkyl) amino,

Cχ-C4-Alkylcarbonyl, Cχ-C4 -Alkoxycarbonyl, Cχ-C -Alk- oxy-Cχ-C -alkoxycarbonyl, Hydroxycarbonyl , Cχ-C4-Al- kylaminocarbonyl, Di - (Cx-C -Alkyl) aminocarbonyl, Aminocarbonyl , Cχ-C4-Alkylcarbonyloxy oder C3-C6-Cycloalkyl;Cχ-C 4 -alkylcarbonyl, Cχ-C 4 -alkoxycarbonyl, Cχ-C -alkoxy-Cχ-C -alkoxycarbonyl, hydroxycarbonyl, Cχ-C 4 -alkylaminocarbonyl, di - (C x -C -alkyl) aminocarbonyl , Aminocarbonyl, Cχ-C 4 alkylcarbonyloxy or C 3 -C 6 cycloalkyl;

Phenyl, Phenyl -Cχ-C6-alkyl, Phenylcarbonyl -Phenyl, phenyl -Cχ-C 6 -alkyl, phenylcarbonyl -

Cχ-C6-alkyl, Phenylcarbonyl, Phenoxycarbonyl , Phen- oxythiocarbonyl , Phenylaminocarbonyl , N- (Cχ-C6-Alkyl) -N-phenylaminocarbonyl ,Cχ-C 6 alkyl, phenylcarbonyl, phenoxycarbonyl, phenoxythiocarbonyl, phenylaminocarbonyl, N- (Cχ-C 6 alkyl) -N-phenylaminocarbonyl,

Phenyl -C2-C6-alkenylcarbonyl, Heterocyclyl, Hetero- cyclyl -Cx -Cδ -alkyl , Heterocyclylcarbonyl -Cx -C6 -alkyl, Heterocyclylcarbonyl , Heterocyclyloxycarbonyl , Heterocyclyloxythiocarbonyl, Heterocyclylaminocarbo- nyl, N- (Cχ-C6-Alkyl) -N-heterocyclylaminocarbonyl oderPhenyl C 2 -C 6 alkenylcarbonyl, heterocyclyl, heterocyclyl -Cx δ -C alkyl, heterocyclylcarbonyl C x -C 6 -alkyl, heterocyclylcarbonyl, heterocyclyloxycarbonyl, Heterocyclyloxythiocarbonyl, Heterocyclylaminocarbo- nyl, N- (Cχ-C 6 -Alkyl) -N-heterocyclylaminocarbonyl or

Heterocyclyl -Cχ-C6-alkenylcarbonyl, wobei der Phenyl - oder der Heterocyclyl -Rest der 18 letztgenannten Sübstituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, Cχ-C -Alkyl, Cχ-C4-Ha- logenalkyl, Cχ-C4 -Alkoxy oder Cχ-C4-Halogenalkoxy;Heterocyclyl -Cχ-C 6 -alkenylcarbonyl, where the phenyl or heterocyclyl radical of the 18 latter substituents can be partially or completely halogenated and / or can carry one to three of the following radicals: nitro, cyano, Cχ-C alkyl, Cχ-C 4 haloalkyl, Cχ-C 4 alkoxy or Cχ-C 4 haloalkoxy;

Cχ-C6 -Alkyl, C3-C6-Alkenyl, C3-C6-Alkinyl oderCχ-C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl or

C3-CÖ -Cycloalkyl, wobei die vier genannten Reste par- tiell oder vollständig halogeniert sein können und/ oder eine bis drei der folgenden Gruppen tragen können: Cyano, Cχ-C4 -Alkoxy, Cχ-C4-Halogenalkoxy, Cχ-C4 -Alkylthio, Cχ-C4-Halogenalkylthio, Cχ-C4-Alkyl- carbonyl, Cχ-C -Alkoxycarbonyl oder Cx -C4-Halogenalk- oxycarbonyl ; Phenyl, Phenyl -C -C -alkyl, Heterocyclyl oder Hetero- cyclyl-Cχ-C4-alkyl, wobei der Phenyl- oder der Hete- rocyclylrest der vier letztgenannten Substituenten partiell oder vollständig halogeniert sein kann und/ oder einen bis drei der folgenden Reste tragen kann:C 3 -C Ö cycloalkyl, where the four radicals mentioned can be partially or completely halogenated and / or can carry one to three of the following groups: cyano, Cχ-C 4 alkoxy, Cχ-C 4 haloalkoxy, Cχ -C 4 alkylthio, Cχ-C 4 haloalkylthio, Cχ-C 4 alkylcarbonyl, Cχ-C alkoxycarbonyl or Cx -C 4 haloalkoxycarbonyl; Phenyl, phenyl-C -C -alkyl, heterocyclyl or heterocyclic-C C-C 4 -alkyl, where the phenyl or heterocyclyl radical of the four last-mentioned substituents can be partially or completely halogenated and / or one to three of the following Can carry leftovers:

Nitro, Cyano, Cχ-C4 -Alkyl, Cχ-C4-Halogenalkyl, Cχ-C -Alkoxy, Cχ-C4 -Halogenalkoxy oder Cχ-C4-Alkoxy- carbonyl ;Nitro, cyano, Cχ-C 4 alkyl, Cχ-C 4 haloalkyl, Cχ-C alkoxy, Cχ-C 4 haloalkoxy or Cχ-C 4 alkoxycarbonyl;

Ri9, R20 Wasserstoff, Hydroxy, Cχ-C6-Alkyl, Cχ-C6-Alkoxy, Cχ-C6-Alkylthio, Phenyl, Phenyl -Cχ-C -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, Cχ-C4-Alkyl, Cχ-C4 -Halogen- alkyl, Cχ-C4 -Alkoxy, Cχ-C4-Halogenalkoxy oder Cx-C -Alkoxycarbonyl ;Ri 9 , R 20 are hydrogen, hydroxy, Cχ-C 6 alkyl, Cχ-C 6 alkoxy, Cχ-C 6 alkylthio, phenyl, phenyl -Cχ-C alkyl or phenoxy, the three latter substituents being partially or completely may be halogenated and / or may carry one to three of the following radicals: nitro, cyano, Cχ-C4-alkyl, Cχ-C4 halo-alkyl, Cχ-C4-alkoxy, Cχ-C4-haloalkoxy or Cx -C alkoxycarbonyl;

R21 Wasserstoff, Cχ-C6-Alkyl, C3-C6-Alkenyl, C3-C6-Halogenalkenyl, C3-C6 -Alkinyl, C3 -C& -Halogen- alkinyl, C3-C6-Cycloalkyl, Cχ-C6-Alkylcarbonyl, Hydroxy, Cχ-C6-Alkoxy, C3-C6-Alkenyloxy, C3 -Cζ -Alkinyloxy, Amino, Cχ-C6-Alkylamino, Di- (Cχ-Cδ- lkyl) amino oder Cχ-Cδ-Alkylcarbonylamino, wobei die genannten Alkyl-, Cycloalkyl- oder Alkoxy- reste partiell oder vollständig halogeniert sein können und/oder einen bis drei der folgenden Reste tragen können: Cyano, Cχ-C4 -Alkoxycarbonyl, Cχ-C -Alkylaminocarbonyl, Di- (Cx -C4-alkyl) amino- carbonyl oder C3 -Cβ -Cycloalkyl;R 21 is hydrogen, Cχ-C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C & haloalkynyl, C 3 -C 6 -Cycloalkyl, Cχ-C 6 alkylcarbonyl, hydroxy, Cχ-C 6 alkoxy, C 3 -C 6 alkenyloxy, C 3 -Cζ alkynyloxy, amino, Cχ-C 6 alkylamino, di- (Cχ-C δ - lkyl) amino or Cχ-C δ alkylcarbonylamino, 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, Cχ-C 4 alkoxycarbonyl , Cχ-C -alkylaminocarbonyl, di- (Cx -C 4 alkyl) amino carbonyl or C 3 -Cβ cycloalkyl;

Phenyl, Phenyl -Cχ-C4- alkyl, Phenylcarbonyl, Heterocyclyl, Heterocyclyl -Cχ-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, Cχ-C -Alkyl, Cχ-C4-Halogenalkyl, Cχ-C4 -Alkoxy oder Cχ-C -Halogenalkoxy;Phenyl, phenyl -Cχ-C 4 -alkyl, phenylcarbonyl, heterocyclyl, heterocyclyl -Cχ-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 to three which may carry the following radicals: nitro, cyano, Cχ-C alkyl, Cχ-C 4 haloalkyl, Cχ-C 4 alkoxy or Cχ-C haloalkoxy;

R22 Wasserstof f , Cχ - C6 -Alkyl , C3 -C6 -Alkenyl oderR 22 hydrogen f, Cχ - C 6 alkyl, C 3 -C 6 alkenyl or

C3 -C6 -Alkinyl ;C 3 -C 6 alkynyl;

p 2 , 3 oder 4 ;p 2, 3 or 4;

q 1 , 2 , 3 , 4 oder 5 . Im Falle von R10 = Hydroxy oder Mercapto {Y = 0, S} steht Ha auch stellvertretend für die tautomeren Formen Ha' , Ha' ' und Ha' ' ' ,q 1, 2, 3, 4 or 5. In the case of R 10 = hydroxy or mercapto {Y = 0, S}, Ha also represents the tautomeric forms Ha ', Ha''andHa''',

Figure imgf000009_0001
bzw. Ilb auch stellvertretend für die tautomeren Formen Ilb' , Ilb' ' und Ilb' ' ' .
Figure imgf000009_0001
and Ilb also represent the tautomeric forms Ilb ', Ilb''andIlb'''.

Figure imgf000009_0002
Figure imgf000009_0002

Die für die Substituenten Ri-R22 oder als Reste an Phenyl-, Heterocyclyl- und N-Heterocyclyl -Resten genannten organischen Molekülteile stellen Sammelbegriffe für individuelle Aufzählungen der einzelnen Gruppenmitglieder dar. Sämtliche Kohlenwasserstof f - ketten, also alle Alkyl-, Halogenalkyl-, Alkoxy-, Halogenalkoxy-, Alkylthio-, Halogenalkylthio-, Alkylsulfinyl-, Halogenalkyl- sulfinyl-, Alkylsulfonyl-, Halogenalkylsulfonyl-, N-Alkylamino- , N,N-Dialkylamino- , N-Halogenalkylamino- , N-Alkoxyamino- , N-Alko- xy-N-alkylamino- , Alkylcarbonyl-, Halogenalkylcarbonyl-, Alkoxy- carbonyl-, Halogenalkoxycarbonyl- , Alkylthiocarbonyl - , Alkyl - carbonyloxy-, Alkylaminocarbonyl-, Dialkylaminocarbonyl-, Dialkylaminothiocarbonyl - , Dialkoxymethyl - , Dialkylthiomethyl - , (Alkoxy) (alkylthio) methyl- , Alkoxyiminoalkyl- , Phenylalkenylcar- bonyl- , Heterocyclylalkenylcarbonyl- , N-Alkoxy-N-alkylaminocarbo- nyl-, N-Alkyl-N-phenylaminocarbonyl-, N-Alkyl-N-heterocyclylami- nocarbonyl-, Phenylalkyl-, Heterocyclylalkyl-, Phenylcarbonylal- kyl-, Heterocyclylcarbonylalkyl-, Alkoxyalkoxycarbonyl-, Alkenyl- carbonyl-, Alkenyloxycarbonyl- , Alkenylaminocarbonyl-, N-Alkenyl- N-alkylaminocarbonyl-, N-Alkenyl-N-alkoxyaminocarbonyl-, Alkinyl - carbonyl-, Alkinyloxycarbonyl- , Alkinylaminocarbonyl-, N-Alkinyl- N-alkylaminocarbonyl-, N-Alkinyl-N-alkoxyaminocarbonyl- , Alkenyl-, Alkinyl-, Halogenalkenyl-, Halogenalkinyl-, Alkenyloxy, Alkinyloxy- , Alkandiyl, Alkendiyl, Alkadiendiyl und Alkindiyl- Teile 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.The organic parts of the molecule mentioned for the substituents Ri-R 22 or as residues on phenyl, heterocyclyl and N-heterocyclyl residues are collective terms for individual lists of the individual group members. All hydrocarbon chains, that is to say all alkyl, haloalkyl, Alkoxy, haloalkoxy, Alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, N-alkylamino, N, N-dialkylamino, N-haloalkylamino, N-alkoxyamino, N-alkoxy-N- alkylamino-, alkylcarbonyl-, haloalkylcarbonyl-, alkoxycarbonyl-, haloalkoxycarbonyl-, alkylthiocarbonyl-, alkyl- carbonyloxy-, alkylaminocarbonyl-, dialkylaminocarbonyl-, dialkylaminothiocarbonyl-, dialkoxymethyl-, dialkylthiomethyl-, (alkoxy )-, alkylthio-, alkylthio-, alkylthio -, Phenylalkenylcarbonyl, heterocyclylalkenylcarbonyl, N-alkoxy-N-alkylaminocarbonyl, N-alkyl-N-phenylaminocarbonyl, N-alkyl-N-heterocyclylamine-nocarbonyl, phenylalkyl, heterocyclylalkyl, phenylcarbonylalkyl -, heterocyclylcarbonylalkyl-, alkoxyalkoxycarbonyl-, alkenylcarbonyl-, alkenyloxycarbonyl-, alkenylaminocarbonyl-, N-alkenyl- N-alkylaminocarbonyl-, N-alkenyl-N-alkoxyaminocarbonyl-, alkynylcarbonyl-, alkynyloxycarbonyl-, alkynylaminocarbonyl Alkynyl-N-alkylamine Ocarbonyl, N-alkynyl-N-alkoxyaminocarbonyl, alkenyl, alkynyl, haloalkenyl, haloalkynyl, alkenyloxy, alkynyloxy, alkanediyl, alkenediyl, alkadienediyl and alkynediyl parts can be straight-chain or branched. Unless stated otherwise, halogenated substituents preferably carry one to five identical or different halogen atoms. Halogen is fluorine, chlorine, bromine or iodine.

Ferner bedeuten beispielsweise:Furthermore, for example:

Cχ-C -Alkyl, sowie die Alkylteile von Phenyl -Cχ-C4-alkyl und Heterocyclyl -Cχ-C4-alkyl: z.B. Methyl, Ethyl, Propyl, 1-Methylethyl, Butyl, 1-Methylpropyl, 2-Methylpropyl oder 1, 1-Dimethylethyl;Cχ-C-alkyl, and the alkyl parts of phenyl -Cχ-C 4 -alkyl and heterocyclyl -Cχ-C 4 -alkyl: for example methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl or 1 , 1-dimethylethyl;

Cχ-C6-Alkyl, sowie die Alkylteile von Cχ-C6-Alkoxyimino-Cχ-C6- alkyl, N-Cχ-C6-Alkoxy-N-Cχ-C6-alkylamino, N(Cχ-C6-Alk- oxy) -N- (Cχ-C6~alkyl) -aminocarbonyl, N- (C3-C6-Al- kenyl) -N- (Cχ-C6-alkyl) -aminocarbonyl, (C3-C6-Alki- nyl) -N- (Cχ-C6~alkyl) -aminocarbonyl, N- (Cχ-C6-Alkyl) -N-phenyla- minocarbonyl, N- (Cχ-C6-Alkyl) -N-heterocyclylaminocarbonyl , Phenyl-Cχ-C6-alkyl, Heterocyclyl-Cχ-C6-alkyl, Phenylcarbo- nyl-Cχ-C6-alkyl, Heterocyclylcarbonyl-Cχ-C6-alkyl : Cχ-C4-Alkyl, wie voranstehend genannt, sowie z.B. Pentyl, 1-Methylbutyl, 2-Methylbutyl, 3-Methylbutyl, 2, 2-Dimethyl- propyl, 1-Ethylpropyl, Hexyl, 1, 1-Dirnethylpropyl, 1,2-Dimethylpropyl, 1-Methylpentyl, 2-Methylpentyl, 3-Methyl- pentyl, 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-Tri- methylpropyl, 1-Ethyl-l-methylpropyl oder l-Ethyl-3-methyl- propyl ;Cχ-C 6 alkyl, and the alkyl parts of Cχ-C6-alkoxyimino-Cχ-C 6 - alkyl, N-Cχ-C 6 -alkoxy-N-Cχ-C 6 -alkylamino, N (Cχ-C 6 -alk - oxy) -N- (Cχ-C 6 ~ alkyl) -aminocarbonyl, N- (C 3 -C 6 -alkenyl) -N- (Cχ-C 6 -alkyl) -aminocarbonyl, (C 3 -C 6 -Alkynyl) -N- (Cχ-C 6 ~ alkyl) -aminocarbonyl, N- (Cχ-C 6 -alkyl) -N-phenyla-minocarbonyl, N- (Cχ-C 6 -alkyl) -N-heterocyclylaminocarbonyl , Phenyl-Cχ-C 6 -alkyl, heterocyclyl-Cχ-C 6 -alkyl, phenylcarbonyl-Cχ-C 6 -alkyl, heterocyclylcarbonyl-Cχ-C 6 -alkyl: Cχ-C 4 -alkyl, as mentioned above, as well as, 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-tri- methylpropyl, 1-ethyl-l-methylpropyl or l-ethyl-3-methylpropyl;

Cχ-C4-Halogenalkyl: einen Cχ-C-Alkylrest, wie vorstehend ge- nannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder Iod substituiert ist, also z.B. Chlormethyl, Dichlormethyl, Trichlormethyl, Fluormethyl, Difluormethyl, Trifluormethyl, Chlorfluormethyl, Dichlorfluormethyl, Chlor- difluormethyl, 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, Pentafluor- ethyl, 2-Fluorpropyl, 3-Fluorpropyl, 2, 2-Difluorpropyl, 2, 3-Difluorpropyl, 2-Chlorpropyl, 3-Chlorpropyl, 2,3-Dichlor- propyl, 2-Brompropyl, 3-Brompropyl, 3, 3, 3-Trifluorpropyl,Cχ-C 4 -haloalkyl: a Cχ-C-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, 2, 2-difluoropropyl, 2,3-difluoropropyl, 2nd Chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3, 3, 3-trifluoropropyl,

3, 3, 3-Trichlorpropyl, 2, 2, 3 , 3, 3-Pentafluorpropyl, Heptafluorpropyl, 1- (Fluormethyl) -2-fluorethyl, 1- (Chlormethyl) -2- chlorethyl, 1- (Brommethyl) -2-bromethyl, 4-Fluorbutyl, 4-Chlorbutyl, 4-Brombutyl oder Nonafluorbutyl;3, 3, 3-trichloropropyl, 2, 2, 3, 3, 3-pentafluoropropyl, heptafluoropropyl, 1- (fluoromethyl) -2-fluoroethyl, 1- (chloromethyl) -2-chloroethyl, 1- (bromomethyl) -2- bromethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl;

Cχ-C6-Halogenalkyl, sowie die Halogenalkylteile von N-Cχ-C6-Halogenalkylamino: Cχ-C4-Halogenalkyl, wie voranstehend genannt, sowie z.B. 5-Fluorpentyl, 5-Chlorpentyl, 5-Brompentyl, 5-Iodpentyl, Undecafluorpentyl, 6-Fluorhexyl, 6-Chlorhexyl, 6-Bromhexyl, 6-Iodhexyl oder Dodecafluorhexyl;Cχ-C 6 -haloalkyl, and the haloalkyl parts of N-Cχ-C 6 -haloalkylamino: Cχ-C 4 -haloalkyl, as mentioned above, and for example 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl, undecafluoropentyl , 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl or dodecafluorohexyl;

Cχ-C4-Alkoxy: z.B. Methoxy, Ethoxy, Propoxy, 1-Methylethoxy, Butoxy, 1-Methylpropoxy, 2-Methylpropoxy oder 1, 1-Dimethyl- ethoxy;Cχ-C 4 alkoxy: for example methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1, 1-dimethylethoxy;

Cχ-C6-Alkoxy, sowie die Alkoxyteile von N-Cχ-C6-Alkoxyamino, Di- (Cχ-C6 -alkoxy)methyl, (Cχ-C6 -Alkoxy) (Cχ-C6 -alkylthio) - methyl, Cχ-C6-Alkoxyimino-Cχ-C6-alkyl, N-Cχ-C6-Alkoxy- N-Cχ-C6-alkylamino, N- (Cχ-C6~Alkoxy) -N- (Cχ-C6-alkyl) -amino- carbonyl, N- (C3-C6~Alkenyl) -N- (Cχ-C6-alkoxy) -aminocarbonyl und N- (C3-C6-Alkinyl) -N- (Cχ-C6-alkoxy) -aminocarbonyl : Cχ-C4-Alkoxy, wie voranstehend genannt, sowie z.B. Pentoxy, 1-Methylbutoxy, 2-Methylbutoxy, 3-Methylbutoxy, 1, 1-Dimethyl- propoxy, 1, 2-Dimethylpropoxy, 2, 2-Dimethylpropoxy, 1-Ethyl- propoxy, Hexoxy, 1-Methylpentoxy, 2-Methylpentoxy, 3-Methyl- pentoxy, 4-Methylpentoxy, 1, 1-Dirnethylbutoxy, 1, 2-Dimethyl- butoxy, 1, 3-Dirnethylbutoxy, 2, 2-Dirnethylbutoxy, 2, 3-Dimethyl- butoxy, 3, 3-Dimethylbutoxy, 1-Ethylbutoxy, 2-Ethylbutoxy, 1,1, 2-Trimethylpropoxy, 1,2, 2-Trimethylpropoxy, 1-Ethyl-l-methylpropoxy oder l-Ethyl-2-methylpropoxy; Cχ-C4-Halogenalkoxy: einen Cχ-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, Bromdi- fluormethoxy, 2-Fluorethoxy, 2-Chlorethoxy, 2-Brommethoxy, 2-lodethoxy, 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-Chlor- propoxy, 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-Fluor- butoxy, 4-Chlorbutoxy, 4-Brombutoxy oder Nonafluorbutoxy;Cχ-C 6 -alkoxy, and the alkoxy parts of N-Cχ-C 6 -alkoxyamino, di- (Cχ-C 6 -alkoxy) methyl, (Cχ-C 6 -alkoxy) (Cχ-C 6 -alkylthio) - methyl , Cχ-C 6 -alkoxyimino-Cχ-C 6 -alkyl, N-Cχ-C 6 -alkoxy- N-Cχ-C 6 -alkylamino, N- (Cχ-C 6 ~ alkoxy) -N- (Cχ-C 6- alkyl) -amino-carbonyl, N- (C 3 -C 6 -alkenyl) -N- (Cχ-C 6 -alkoxy) -aminocarbonyl and N- (C 3 -C 6 -alkynyl) -N- (Cχ -C 6 -alkoxy) -aminocarbonyl: Cχ-C 4 -alkoxy, as mentioned above, and for example pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1, 1-dimethylpropoxy, 1, 2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethyl-propoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3- Dirnethylbutoxy, 2, 2-Dirnethylbutoxy, 2, 3-Dimethylbutoxy, 3, 3-Dimethylbutoxy, 1-Ethylbutoxy, 2-Ethylbutoxy, 1,1, 2-Trimethylpropoxy, 1,2, 2-Trimethylpropoxy, 1-Ethyl l-methylpropoxy or l-ethyl-2-methylpropoxy; Cχ-C 4 haloalkoxy: a Cχ-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, bromodi-fluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromomethoxy, 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- Difluorpropoxy, 2, 3-Difluorpropoxy, 2, 3-Dichlorpropoxy, 3, 3, 3-Trifluorpropoxy, 3,3,3-Trichlorpropoxy, 2, 2, 3, 3, 3-Pentafluorpropoxy, Heptafluorpropoxy, 1- (fluoromethyl) - 2-fluoroethoxy, 1- (chloromethyl) -2-chloroethoxy, 1- (bromomethyl) -2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy;

Cχ-Cδ-Halogenalkoxy: Cχ-C4-Halogenalkoxy, wie voranstehend genannt, sowie z.B. 5-Fluorpentoxy, 5-Chlorpentoxy, 5-Brompent- oxy, 5-Iodpentoxy, Undecafluorpentoxy, 6-Fluorhexoxy, 6-Chlorhexoxy, 6-Bromhexoxy, 6-Iodhexoxy oder Dodecafluorhex- oxy;Cχ-C δ -haloalkoxy: Cχ-C 4 -haloalkoxy, as mentioned above, and for example 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorhexoxy, 6-chlorohexoxy, 6- Bromhexoxy, 6-iodohexoxy or dodecafluorohexoxy;

Cχ-C4-Alkylthio: z.B. Methylthio, Ethylthio, Propylthio, 1-Methylethylthio, Butylthio, 1-Methylpropylthio, 2-Methyl- propylthio oder 1, 1-Dimethylethylthio;Cχ-C 4 alkylthio: for example methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio or 1, 1-dimethylethylthio;

Cχ-C6-Alkylthio, sowie die Alkylthioteile von Cx -Ce ~Alkylthio- carbonyl, Di- (Cχ-C6-alkylthio) methyl undCχ-C 6 -Alkylthio, and the alkylthio parts of Cx -Ce ~ alkylthio-carbonyl, di- (Cχ-C 6 -alkylthio) methyl and

(Cχ-C6 -Alkoxy) (Cχ-Cδ-alkylthio) methyl: Cχ-C -Alkylthio, wie voranstehend genannt, sowie z.B. Pentylthio, 1-Methylbutyl- thio, 2-Methylbutylthio, 3-Methylbutylthio, 2 , 2-Dimethyl- propylthio, 1-Ethylpropylthio, Hexylthio, 1, 1-Dimethylpropyl- thio, 1,2-Dimethylpropylthio, 1-Methylpentylthio, 2-Methyl- pentylthio, 3-Methylpentylthio, 4-Methylpentylthio, 1, 1-Dimethylbutylthio, 1, 2-Dimethylbutylthio, 1, 3-Dimethyl- butylthio, 2, 2-Dimethylbutylthio, 2 , 3-Dimethylbutylthio, 3, 3-Dimethylbutylthio, 1-Ethylbutylthio, 2-Ethylbutylthio, 1, 1, 2-Trimethylpropylthio, 1,2, 2-Trimethylpropylthio, 1-Ethyl-l-methylpropylthio oder l-Ethyl-2-methylpropylthio;(Cχ-C 6 -alkoxy) (Cχ-C δ- alkylthio) methyl: Cχ-C -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-methylpentylthio, 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-trimethylpropylthio, 1-ethyl-l-methylpropylthio or l-ethyl-2-methylpropylthio;

Cχ-C4-Halogenalkylthio: einen Cχ-C4-Alkylthiorest, wie voranstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder Iod substituiert ist, also z.B. Fluor- methylthio, Difluormethylthio, Trifluormethylthio, Chlor- difluormethylthio, Bromdifluormethylthio, 2-Fluorethylthio, 2-Chlorethylthio, 2-Bromethylthio, 2-Iodethylthio, 2, 2-Difluorethylthio, 2 , 2 , 2-Trifluorethylthio, 2,2,2-Tri- chlorethylthio, 2-Chlor-2-fluorethylthio,Cχ-C 4 haloalkylthio: a Cχ-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-tri- chloroethylthio, 2-chloro-2-fluoroethylthio,

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-Difluorpropyl - thio, 2 , 3-Dichlorpropylthio, 3 , 3 , 3-Trifluorpropylthio, 3,3, 3-Trichlorpropylthio, 2 , 2, 3 , 3 , 3-Pentafluorpropylthio, Heptafluorpropylthio, 1- (Fluormethyl) -2-fluorethylthio, 1- (Chlormethyl) -2-chlorethylthio, 1- (Brommethyl) -2-bromethyl- thio, 4-Fluorbutylthio, 4-Chlorbutylthio, 4-Brombutylthio oder Nonafluorbutylthio;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-dichloropropylthio, 3, 3, 3-trifluoropropylthio, 3,3, 3-trichloropropylthio, 2, 2, 3, 3, 3-pentafluoropropylthio, heptafluoropropylthio ) -2-fluoroethylthio, 1- (chloromethyl) -2-chloroethylthio, 1- (bromomethyl) -2-bromomethylthio, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio or nonafluorobutylthio;

Cχ-C6-Halogenalkylthio: Cχ-C4-Halogenalkylthio, wie voranstehend genannt, sowie z.B. 5-Fluorpentylthio, 5-Chlorpen- tylthio, 5-Brompentylthio, 5-Iodpentylthio, Undecafluorpen- tylthio, 6-Fluorhexylthio, 6-Chlorhexylthio, 6-Bromhexylthio, 6-Iodhexylthio oder Dodecaflu.orhexylth.io;Cχ-C 6 -haloalkylthio: Cχ-C 4 -haloalkylthio, as mentioned above, and for example 5-fluoropentylthio, 5-chloropentylthio, 5-bromopentylthio, 5-iodopentylthio, undecafluoropentylthio, 6-fluorhexylthio, 6-chlorohexylthio, 6-bromohexylthio, 6-iodohexylthio or dodecafluorohexylthio;

Cχ-C4-Alkylsulfinyl (Cχ-C4-Alkyl-S (=0) -) : z.B. Methylsulfinyl, Ethylsulfinyl, Propylsulfinyl, 1-Methylethylsulfinyl, Butyl- sulfinyl, 1-Methylpropylsulfinyl, 2-Methylpropylsulfinyl oder 1, 1-Dimethylethylsulfinyl;Cχ-C 4 -alkylsulfinyl (Cχ-C 4 -alkyl-S (= 0) -): e.g. methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl or 1, 1-dimethylethylsulfinyl ;

C -C6-Alkylsufinyl (Cχ-C6-Alkyl-S (=0) - ) : Cχ-C4-Alkylsulfinyl, wie vorausstehend genannt, sowie Pentylsulfinyl, 1-Methylbu- tylsulfinyl, 2-Methylbutyisulfinyl, 3-Methylbutylsulfinyl, 2, 2-Dimethylpropylsulfinyl, 1-Ethylpropylsulfinyl, 1,1-Dime- thylpropylsulfinyl, 1, 2-Dimethylpropylsulfinyl, Hexylsulfi- nyl, 1-Methylpentylsulfinyl, 2-Methylpentylsulfinyl, 3-Me- thylpentylsulfinyl, 4-Methylpentylεulfinyl, 1, 1-Dimethylbu- tylsulfinyl, 1, 2-Dimethylbutylsulfinyl, 1, 3-Dimethylbutylsul- finyl, 2, 2-Dimethylbutylsulfinyl, 2 , 3-Dimethylbutylsulfinyl, 3,3-Dimethylbutylsulfinyl, 1-Ethylbutylsulfinyl, 2-Ethylbu- tylsulfinyl, 1, 1, 2-Trimethylpropylsulfinyl, 1,2, 2-Trimethyl- propylsulfinyl, 1-Ethyl-l-methylpropylsulfinyl oder l-Ethyl-2-methylpropylsulfinyl ;C -C 6 -alkylsufinyl (Cχ-C 6 -alkyl-S (= 0) -): Cχ-C 4 -alkylsulfinyl, as mentioned above, and pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutysulfinyl, 3-methylbutylsulfinyl, 2, 2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, 1,1-dimethylpropylsulfinyl, 1, 2-dimethylpropylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylεulfinyl Dimethylbutylsulfinyl, 1, 2-dimethylbutylsulfinyl, 1, 3-dimethylbutylsulfinyl, 2, 2-dimethylbutylsulfinyl, 2, 3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl 2-trimethylpropylsulfinyl, 1,2, 2-trimethylpropylsulfinyl, 1-ethyl-l-methylpropylsulfinyl or l-ethyl-2-methylpropylsulfinyl;

Cχ-C4-Halogenalkylsulfinyl: Cχ-C4~Alkylsulfinylrest, wie voranstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder Iod substituiert ist, also z.B. Fluormethylsulfinyl, Difluormethylsulfinyl, Trifluormethyl- sulfinyl, Chlordifluormethylsulfinyl, Bromdifluormethylsulfi- nyl, 2-Fluorethylsulfinyl, 2-Chlorethylsulfinyl, 2-Bromethyl- sulfinyl, 2-Iodethylsulfinyl, 2, 2-Difluorethylsulfinyl, 2, 2, 2-Trifluorethylsulfinyl, 2, 2, 2-Trichlorethylsulfinyl,Cχ-C 4 -haloalkylsulfinyl: Cχ-C 4 ~ alkylsulfinyl, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example fluoromethylsulfinyl, difluoromethylsulfinyl, trifluoromethylsulfinyl, chlorodifluoromethylsulfinyl, bromodifluoromethylsulfinyl , 2-fluoroethylsulfinyl, 2-chloroethylsulfinyl, 2-bromoethylsulfinyl, 2-iodoethylsulfinyl, 2, 2-difluoroethylsulfinyl, 2, 2, 2-trifluoroethylsulfinyl, 2, 2, 2-trichloroethylsulfinyl,

2-Chlor-2-fluorethylsulfinyl , 2-Chlor-2 , 2-difluorethylsulfi - nyl, 2, 2-Dichlor-2-fluorethylsulfinyl, Pentafluorethylsulfi- nyl, 2-Fluorpropylsulfinyl, 3-Fluorpropylsulfinyl, 2-Chlor- propylsulfinyl, 3-Chlorpropylsulfinyl, 2-Brompropylsulfinyl, 3-Brompropylsulfinyl, 2, 2-Difluorpropylsulfinyl, 2, 3-Difluorpropylsulfinyl, 2, 3-Dichlorpropylsulfinyl, 3, 3, 3-Trifluorpro- pylsulfinyl, 3, 3, 3-Trichlorpropylsulfinyl, 2, 2, 3, 3, 3-Penta- fluorpropylsulfinyl, Heptafluorpropylsulfinyl, 1- (Fluormethyl) -2-fluorethylsulfinyl, 1- (Chlormethyl) -2-chlorethyl- sulfinyl, 1- (Brommethyl) -2-bromethylsulfinyl, 4-Fluorbutyl- sulfinyl, 4-Chlorbutylsulfinyl, 4-Brombutylsulfinyl oder No- nafluorbutylsulfinyl;2-chloro-2-fluoroethylsulfinyl, 2-chloro-2, 2-difluoroethylsulfinyl - nyl, 2, 2-dichloro-2-fluoroethylsulfinyl, pentafluoroethylsulfinyl nyl, 2-fluoropropylsulfinyl, 3-fluoropropylsulfinyl, 2-chloropropylsulfinyl, 3-chloropropylsulfinyl, 2-bromopropylsulfinyl, 3-bromopropylsulfinyl, 2, 2-difluoropropylsulfinyl, 2, 3-difluoropropylsulfinyl, 2, 3, 3-dichloromethyl 3-trifluoropropylsulfinyl, 3, 3, 3-trichloropropylsulfinyl, 2, 2, 3, 3, 3-pentafluoropropylsulfinyl, heptafluoropropylsulfinyl, 1- (fluoromethyl) -2-fluoroethylsulfinyl, 1- (chloromethyl) -2-chloroethyl- sulfinyl, 1- (bromomethyl) -2-bromethylsulfinyl, 4-fluorobutylsulfinyl, 4-chlorobutylsulfinyl, 4-bromobutylsulfinyl or nonafluorobutylsulfinyl;

Cχ-C6-Halogenalkylsulfinyl: Cχ-C4-Halogenalkylsulfinyl wie voranstehend genannt, sowie 5-Fluorpentylsulfinyl, 5-Chlor- pentylsulfinyl, 5-Brompen-ylsulfinyl, 5-Iodpentylsulfinyl, Undecafluorpentylsulfinyl, 6-Fluorhexylsulfinyl, 6-Chlorhe- xylsulfinyl, 6-Bromhexyls finyl, 6-Iodhexylsulfinyl oder Do- decafluorhexylsulfinyl;Cχ-C 6 -haloalkylsulfinyl: Cχ-C 4 -haloalkylsulfinyl as mentioned above, as well as 5-fluoropentylsulfinyl, 5-chloropentylsulfinyl, 5-bromopen-ylsulfinyl, 5-iodopentylsulfinyl, undecafluoropentylsulfinyl, 6-fluorohexylsulfinyl, 6-chlorosulfinyl 6-bromohexyls finyl, 6-iodohexylsulfinyl or dodecafluorohexylsulfinyl;

Cχ-C4-Alkylsulfonyl (Cχ-C4-Alkyl-S (=0) 2-) : z.B. Methyl- sulfonyl, Ethylsulfonyl, Propylsulfonyl, 1-Methylethyl- sulfonyl, Butylsulfonyl, I-Methylpropylsulfonyl, 2-Methyl- propylsulfonyl oder 1, 1-Dimethylethylsulfonyl;Cχ-C 4 -alkylsulfonyl (Cχ-C 4 -alkyl-S (= 0) 2 -): e.g. methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, I-methylpropylsulfonyl, 2-methylpropylsulfonyl or 1, 1-dimethylethylsulfonyl;

Cχ-C6 -Alkylsulfonyl (Cχ-C6 -Alkyl -S (=0) 2- ) : Cχ-C4 -Alkylsulfonyl wie voranstehend genannt, sowie Pentylsulfonyl, 1-Methyl- butylsulfonyl, 2-Methylb tylsulfonyl, 3-Methylbutylsulfonyl, 1, 1-Dimethylpropylsulfonyl, 1, 2-Dimethylpropylsulfonyl, 2, 2-Dimethylpropylsulfonyl, 1-Ethylpropylsulfonyl, Hexyl- sulfonyl, 1-Methylpentylsulfonyl, 2-Methylpentylsulfonyl, 3-Methylpentylsulfonyl, 4-Methylpentylsulfonyl, 1, 1-Dimethyl- butylsulfonyl, 1, 2-Dimethylbutylsulfonyl, 1 , 3-Dimethylbutyl - sulfonyl, 2, 2-Dimethylbucylsulfonyl, 2, 3-Dimethylbutyl - sulfonyl, 3 , 3-Dimethylbutylsulfonyl, 1-Ethylbutylsulfonyl, 2-Ethylbutylsulfonyl, 1,1, 2-Trimethylpropylsulfonyl, 1,2, 2-Trimethylpropylsulfonyl, 1-Ethyl-l-methylpropylsulfonyl oder l-Ethyl-2-methylpropylsulfonyl;Cχ-C 6 -alkylsulfonyl (Cχ-C 6 -alkyl -S (= 0) 2 -): Cχ-C 4 -alkylsulfonyl as mentioned above, and pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylb tylsulfonyl, 3-methylbutylsulfonyl , 1, 1-dimethylpropylsulfonyl, 1, 2-dimethylpropylsulfonyl, 2, 2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 4-methylpentylsulfonyl, 4-methylpentylsulfonyl , 1, 2-dimethylbutylsulfonyl, 1, 3-dimethylbutylsulfonyl, 2, 2-dimethylbucylsulfonyl, 2, 3-dimethylbutylsulfonyl, 3, 3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonylprop. 1,1 , 1,2, 2-trimethylpropylsulfonyl, 1-ethyl-l-methylpropylsulfonyl or l-ethyl-2-methylpropylsulfonyl;

Cχ-C4-Halogenalkylsulfonyl: einen Cχ-C4-Alkylsulfonylrest, wie voranstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder Iod substituiert ist, also z.B. Fluormethylsulfonyl, Difluormethylsulfonyl, Trifluormethylsulfonyl, Chlordifluormethylsulfonyl, Bromdifluormethylsulfo- nyl, 2-Fluorethylsulfonyl, 2-Chlorethylsulfonyl, 2-Bromethyl- sulfonyl, 2-Iodethylsulfonyl, 2, 2-Difluorethylsulfonyl, 2, 2, 2-Trifluorethylsulfonyl, 2-Chlor-2-fluorethylsulfonyl, 2-Chlor-2 , 2-difluorethylsulfonyl , 2 , 2-Dichlor-2-fluorethyl - sulfonyl, 2 , 2, 2-Trichlorethylsulfonyl, Pentafluorethyl- sulfonyl, 2-Fluorpropylsulfonyl, 3-Fluorpropylsulfonyl, 2-Chlorpropylsulfonyl, 3-Chlorpropylsulfonyl, 2-Brompropyl- sulfonyl, 3-Brompropylsulfonyl, 2 , 2-Difluorpropylsulfonyl, 2, 3-Difluorpropylsulfonyl, 2 , 3-Dichlorpropylsulfonyl, 3, 3, 3-Trifluorpropylsulfonyl, 3 , 3 , 3-Trichlorpropylsulfonyl,Cχ-C 4 haloalkylsulfonyl: a Cχ-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, chlorodifluoromethyldifluoromethyl, 2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl, 2, 2-difluoroethylsulfonyl, 2, 2, 2-trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl, 2-chloro-2, 2-difluoroethylsulfonyl, 2,2-dichloro-2-fluoroethylsulfonyl, 2,2,2-trichloroethylsulfonyl, pentafluoroethyl sulfonyl, 2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl, 2-chloropropylsulfonyl, 3-chloropropylsulfonyl, 2-bromopropylsulfonyl, 3-bromopropylsulfonyl, 2, 2-difluoropropylsulfonyl, 2, 3-difluoronyl, 3-sulfonyl, 3-sulfonyl, 3-sulfonyl, 3-trifluoropropylsulfonyl, 3, 3, 3-trichloropropylsulfonyl,

2,2,3,3, 3-Pentafluorpropylsulfonyl, Heptafluorpropylsulfonyl, 1- (Fluormethyl)-2-fluorethylsulfonyl, 1- (Chlormethyl) -2-chlo- rethylsulfonyl, 1- (Brommethyl) -2-bromethylsulfonyl, 4-Fluor- butylsulfonyl, 4-Chlorbutylsulfonyl, 4-Brombutylsulfonyl oder Nonafluorbutylsulfonyl ;2,2,3,3, 3-pentafluoropropylsulfonyl, heptafluoropropylsulfonyl, 1- (fluoromethyl) -2-fluoroethylsulfonyl, 1- (chloromethyl) -2-chloroethylsulfonyl, 1- (bromomethyl) -2-bromomethylsulfonyl, 4-fluoro- butylsulfonyl, 4-chlorobutylsulfonyl, 4-bromobutylsulfonyl or nonafluorobutylsulfonyl;

Cχ-C6-Halogenalkylsulfonyl: Cχ-C -Halogenalkylsulfonyl wie voranstehend genannt, sowie 5-Fluorpentylsulfonyl, 5-Chlor- pentylsulfonyl, 5-Brompentylsulfonyl, 5-Iodpentylsulfonyl, 6-Fluorhexylsulfonyl, 6-Bromhexylsulfonyl, 6-Iodhexylsulfonyl oder Dodecafluorhexylsulfonyl ;Cχ-C 6 -haloalkylsulfonyl: Cχ-C -haloalkylsulfonyl as mentioned above, and 5-fluoropentylsulfonyl, 5-chloropentylsulfonyl, 5-bromopentylsulfonyl, 5-iodopentylsulfonyl, 6-fluorohexylsulfonyl, 6-bromhexylsulfonylylylsulfonyl;

Cχ-C6-Alkylamino: z.B. Methylamino, Ethylamino, Propylamino, 1-Methylethylamino, Butylamino, 1-Methylpropylamino, 2-Methylpropylamino, 1, 1-Dimethylethylamino, Pentylamino,Cχ-C 6 -alkylamino: for example methylamino, ethylamino, propylamino, 1-methylethylamino, butylamino, 1-methylpropylamino, 2-methylpropylamino, 1, 1-dimethylethylamino, pentylamino,

1-Methylbutylamino, 2-Methylbutylamino, 3-Methylbutylamino, 2, 2-Dirnethylpropylamino, 1-Ethylpropylamino, Hexylamino, 1, 1-Dirnethylpropylamino, 1, 2-Dimethylpropylamino, 1-Methyl - pentylamino, 2-Methylpentylamino, 3-Methylpentylamino, 4-Methylpentylamino, 1, 1-Dimethylbutylamino, 1, 2-Dimethyl- butylamino, 1, 3-Dimethylbutylamino, 2, 2-Dimethylbutylamino, 2 , 3-Dimethylbutylamino, 3 , 3-Dimethylbutylamino, 1-Ethylbutyl - amino, 2-Ethylbutylamino, 1, 1, 2-Trimethylpropylamino, 1,2, 2-Trimethylpropylamino, 1-Ethyl-l-methylpropylamino oder l-Ethyl-2-methylpropylamino;1-Methylbutylamino, 2-Methylbutylamino, 3-Methylbutylamino, 2, 2-Dirnethylpropylamino, 1-Ethylpropylamino, Hexylamino, 1, 1-Dirnethylpropylamino, 1, 2-Dimethylpropylamino, 1-Methyl - pentylamino, 2-Methylpentylamino 4-methylpentylamino, 1, 1-dimethylbutylamino, 1, 2-dimethylbutylamino, 1, 3-dimethylbutylamino, 2, 2-dimethylbutylamino, 2, 3-dimethylbutylamino, 3, 3-dimethylbutylamino, 1-ethylbutylamino, 2- Ethyl butylamino, 1, 1, 2-trimethylpropylamino, 1,2, 2-trimethylpropylamino, 1-ethyl-l-methylpropylamino or l-ethyl-2-methylpropylamino;

Di- (Cχ-C4-alkyl) amino: z.B. N,N-Dimethylamino, N,N-Diethyl- amino, 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, 1-dimethylethyl) - amino, N-Ethyl-N-methylamino, N-Methyl-N-propylamino, N-Me- thyl-N- (1-methylethyl) amino, N-Butyl-N-methylamino, N-Me- thyl-N- (1-methylpropyl) amino, N-Methyl-N- (2-methyl- propyl ) amino, N- (1, 1-Dimethylethyl) -N-methylamino, N-Ethyl-N- propylamino, N-Ethyl-N- (1-methylethyl) amino, N-Butyl-N-ethyl- amino, N-Ethyl-N- (1-methylpropyl) amino, N-Ethyl-N- (2-methylpropyl) amino, N-Ethyl-N- (1, 1-dimethylethyl) amino, N-(1-Me- thylethyl) -N-propylamino, N-Butyl-N-propylamino, N-(1-Methyl- propyl ) -N-propylamino, N- (2-Methylpropyl) -N-propylamino, 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-Dimethyl- ethyl) -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;Di- (Cχ-C 4 -alkyl) amino: for example N, N-dimethylamino, N, N-diethylamino, 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, 1-dimethylethyl) amino, N-ethyl-N -methylamino, N-methyl-N-propylamino, N-methyl-N- (1-methylethyl) amino, N-butyl-N-methylamino, N-methyl-N- (1-methylpropyl) amino, N -Methyl-N- (2-methyl-propyl) amino, N- (1, 1-dimethylethyl) -N-methylamino, N-ethyl-N-propylamino, N-ethyl-N- (1-methylethyl) amino, N -Butyl-N-ethyl-amino, N-ethyl-N- (1-methylpropyl) amino, N-ethyl-N- (2-methylpropyl) amino, N-ethyl-N- (1, 1-dimethylethyl) amino, N- (1-methylethyl) -N-propylamino, N-butyl-N-propylamino, N- (1-methylpropyl) -N-propylamino, N- (2-methylpropyl) -N-propylamino, 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-dimethyl- ethyl) -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- (Cχ-C6 -alkyl) amino: Di- (Cχ-C -alkyl) amino wie voranstehend genannt, sowie N,N-Dipentylamino, N,N-Dihexylamino, N-Methyl- N-pentylamino, N-Ethyl-N-pentylamino, N-Methyl -N-hexylamino oder N-Ethyl-N-hexylamino.Di- (Cχ-C 6 -alkyl) amino: Di- (Cχ-C -alkyl) amino as mentioned above, and N, N-dipentylamino, N, N-dihexylamino, N-methyl-N-pentylamino, N-ethyl -N-pentylamino, N-methyl -N-hexylamino or N-ethyl-N-hexylamino.

Cχ-C4-Alkylcarbonyl: z.B. Methylcarbonyl, Ethylcarbonyl, Propylcarbonyl, 1-Methylethylcarbonyl, Butylcarbonyl, 1-Methylpropylcarbonyl, 2-Methylpropylcarbonyl oder 1 , 1-Dimethylethylcarbonyl;Cχ-C 4 alkylcarbonyl: for example methylcarbonyl, ethylcarbonyl, propylcarbonyl, 1-methylethylcarbonyl, butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl or 1, 1-dimethylethylcarbonyl;

Cχ-C6 _Alkylcarbonyl: Cχ-C4-Alkylcarbonyl, wie voranstehend genannt, sowie z.B. Pentylcarbonyl, 1-Methylbutylcarbonyl, 2-Methylbutylcarbonyl, 3-Methylbutylcarbonyl, 2,2-Dimethyl- propylcarbonyl , 1-Ethylpropylcarbonyl, Hexylcarbonyl,Cχ-C 6 _ alkylcarbonyl: Cχ-C 4 alkylcarbonyl, as mentioned above, and for example pentylcarbonyl, 1-methylbutylcarbonyl, 2-methylbutylcarbonyl, 3-methylbutylcarbonyl, 2,2-dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, hexylcarbonyl,

1 , 1-Dimethylpropylcarbonyl , 1, 2-Dirnethylpropylcarbonyl, 1-Methylpentylcarbonyl, 2-Methylpentylcarbonyl, 3-Methyl- pentylcarbonyl , 4-Methylpentylcarbonyl, 1, 1-Dimethylbutyl- carbonyl , 1 , 2-Dimethylbutylcarbonyl , 1 , 3-Dimethylbutyl - carbonyl , 2,2, -Dimethylbutylcarbonyl, 2 , 3-Dimethylbutyl- carbonyl, 3, 3-Dimethylbutylcarbonyl, 1-Ethylbutylcarbonyl, 2-Ethylbutylcarbonyl , 1,1, 2-Trimethylpropylcarbonyl, 1,2, 2-Trimethylpropylcarbonyl, 1-Ethyl-l-methylpropylcarbonyl oder l-Ethyl-2-methylpropylcarbonyl;1, 1-dimethylpropylcarbonyl, 1, 2-dimethylpropylcarbonyl, 1-methylpentylcarbonyl, 2-methylpentylcarbonyl, 3-methylpentylcarbonyl, 4-methylpentylcarbonyl, 1, 1-dimethylbutylcarbonyl, 1, 2-dimethylbutylcarbonyl, 1, 3-dimethylbutyl - carbonyl, 2,2, -dimethylbutylcarbonyl, 2, 3-dimethylbutylcarbonyl, 3, 3-dimethylbutylcarbonyl, 1-ethylbutylcarbonyl, 2-ethylbutylcarbonyl, 1,1, 2-trimethylpropylcarbonyl, 1,2, 2-trimethylpropylcarbonyl, 1-ethyl -l-methylpropylcarbonyl or l-ethyl-2-methylpropylcarbonyl;

Cχ-C4-Halogenalkylcarbonyl: einen Cχ-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, Dichlorfluo- racetyl, Chlordifluoracetyl, 2-Fluorethylcarbonyl, 2-Chlor- ethylcarbonyl, 2-Bromethylcarbonyl, 2-Iodethylcarbonyl, 2 , 2-Difluorethylcarbonyl , 2,2, 2-Trifluorethylcarbonyl, 2-Chlor-2-fluorethylcarbonyl, 2-Chlor-2, 2-difluorethylcarbo- nyl, 2, 2-Dichlor-2-fluorethylcarbonyl, 2, 2, 2-Trichlorethyl- carbonyl, Pentafluorethylcarbonyl, 2-Fluorpropylcarbonyl, 3-Fluorpropylcarbonyl, 2, 2-Difluorpropylcarbonyl, 2,3-Diflu- orpropylcarbonyl, 2-Chlorpropylcarbonyl, 3-Chlorpropylcarbo- nyl, 2, 3-Dichlorpropylcarbonyl, 2-Brompropylcarbonyl, 3-Brom- propylcarbonyl, 3, 3, 3-Trifluorpropylcarbonyl, 3,3, 3-Trichlor- propylcarbonyl, 2, 2, 3, 3, 3-Pentafluorpropylcarbonyl, Heptafluorpropylcarbonyl, 1- (Fluormethyl) -2-fluorethylcarbonyl, 1- (Chlormethyl) -2-chlorethylcarbonyl, 1- (Brommethyl) -2-brome- thylcarbonyl, 4-Fluorbutylcarbonyl, 4-Chlorbutylcarbonyl, 4-Brombutylcarbonyl oder Nonafluorbutylcarbonyl ;Cχ-C 4 haloalkylcarbonyl: a Cχ-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, dichlorofluoracetyl, chlorodifluoroacetyl, 2-fluoroethylcarbonyl, 2-chloroethylcarbonyl, 2-bromoethylcarbonyl, 2-iodoethylcarbonyl, 2, 2-difluoroethylcarbonyl, 2,2, 2-trifluoroethylcarbonyl, 2-chloro-2-fluoroethylcarbonyl, 2- Chloro-2, 2-difluoroethylcarbonyl, 2, 2-dichloro-2-fluoroethylcarbonyl, 2, 2, 2-trichloroethylcarbonyl, pentafluoroethylcarbonyl, 2-fluoropropylcarbonyl, 3-fluoropropylcarbonyl, 2, 2-difluoropropylcarbonyl, 2,3- Difluoropropylcarbonyl, 2-chloropropylcarbonyl, 3-chloropropylcarbonyl, 2, 3-dichloropropylcarbonyl, 2-bromopropylcarbonyl, 3-bromopropylcarbonyl, 3, 3, 3-trifluoropropylcarbonyl, 3,3, 3-trichloropropylcarbonyl, 2, 2, 3, 3, 3-pentafluoropropylcarbonyl, heptafluoropropylcarbonyl, 1- (Fl uormethyl) -2-fluoroethylcarbonyl, 1- (chloromethyl) -2-chloroethylcarbonyl, 1- (bromomethyl) -2-bromomethylcarbonyl, 4-fluorobutylcarbonyl, 4-chlorobutylcarbonyl, 4-bromobutylcarbonyl or nonafluorobutylcarbonyl;

- Cχ-C6-Halogenalkylcarbonyl : einen Cχ-C4-Halogenalkylcarbonyl- rest wie voranstehend genannt, sowie 5-Fluorpentylcarbonyl, 5-Chlorpentylcarbonyl, 5 -Brompentylcarbonyl, Perfluorpentyl - carbonyl, 6-Fluorhexylcarbonyl, 6 -Chlorhexylcarbonyl, 6-Brom- hexylcarbonyl oder Perfluorhexylcarbonyl;Cχ-C 6 -haloalkylcarbonyl: a Cχ-C 4 -haloalkylcarbonyl radical as mentioned above, and 5-fluoropentylcarbonyl, 5-chloropentylcarbonyl, 5 -bromopentylcarbonyl, perfluoropentylcarbonyl, 6-fluorhexylcarbonyl, 6 -chlorohexylcarbonyl, 6-bromo- hexylcarbonyl or perfluorohexylcarbonyl;

Cχ-C4-Alkoxycarbonyl, sowie die Alkoxycarbonylteile von Di- (Cχ-C4-alkyl) amino-Cχ-C4-alkoxycarbonyl, also z.B. Methoxy- carbonyl, Ethoxycarbonyl, Propoxycarbonyl , 1-Methylethoxy- carbonyl, Butoxycarbonyl , 1-Methylpropoxycarbonyl, 2-Methyl- propoxycarbonyl oder 1, 1-Dimethylethoxycarbonyl;Cχ-C 4 -alkoxycarbonyl, and the alkoxycarbonyl parts of di- (Cχ-C 4 -alkyl) amino-Cχ-C 4 -alkoxycarbonyl, i.e. for example methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, 1-methylethoxycarbonyl, butoxycarbonyl, 1- Methylpropoxycarbonyl, 2-methylpropoxycarbonyl or 1, 1-dimethylethoxycarbonyl;

(Cχ-C6~Alkoxy) carbonyl : (Cχ-C4-Alkoxy) carbonyl, wie vorstehend genannt, sowie z.B. Pentoxycarbonyl , 1-Methylbutoxycarbonyl, 2-Methylbutoxycarbonyl, 3-Methylbutoxycarbonyl, 2 , 2-Dimethyl- propoxycarbonyl, 1-Ethylpropoxycarbonyl, Hexoxycarbonyl, 1, 1-Dirnethylpropoxycarbonyl, 1, 2-Dimethylpropoxycarbonyl, 1-Methylpentoxycarbonyl, 2-Methylpentoxycarbonyl, 3-Methyl- pentoxycarbonyl, 4-Methylpentoxycarbonyl, 1, 1-Dimethylbutoxy- carbonyl , 1,2-Dimethylbutoxycarbony1, 1,3-Dimethylbutoxycar- bonyl, 2, 2-Dimethylbutoxycarbonyl, 2, 3-Dimethylbutoxycarbo- nyl, 3, 3-Dimethylbutoxycarbonyl, 1-Ethylbutoxycarbonyl, 2-Ethylbutoxycarbonyl, 1,1, 2-Trimethylpropoxycarbonyl,(Cχ-C 6 ~ alkoxy) carbonyl: (Cχ-C 4 -alkoxy) carbonyl, as mentioned above, and for example pentoxycarbonyl, 1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 2, 2-dimethyl-propoxycarbonyl, 1- Ethylpropoxycarbonyl, Hexoxycarbonyl, 1, 1-Dirnethylpropoxycarbonyl, 1, 2-Dimethylpropoxycarbonyl, 1-Methylpentoxycarbonyl, 2-Methylpentoxycarbonyl, 3-Methyl-pentoxycarbonyl, 4-Methylpentoxycarbonyl, 1, 1-Dimethylbutoxycarbonyl, 1,2-Dimethylbutoxycarbonony1, 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-propoxycar- bonyl oder l-Ethyl-2-methyl-propoxycarbonyl;1,2, 2-trimethylpropoxycarbonyl, 1-ethyl-l-methyl-propoxycarbonyl or l-ethyl-2-methyl-propoxycarbonyl;

Cχ-C4-Halogenalkoxycarbonyl : einen Cχ-C4-Alkoxycarbonylrest, wie voranstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder Iod substituiert ist, also z.B. Fluormethoxycarbonyl, Difluormethoxycarbonyl, Trifluormetho- xycarbonyl, Chlordifluormethoxycarbonyl, Bromdifluormethoxycarbonyl, 2-Fluorethoxycarbonyl, 2-Chlorethoxycarbonyl, 2-Bromethoxycarbonyl, 2-Iodethoxycarbonyl, 2, 2-Difluorethoxy- carbonyl , 2,2, 2-Trifluorethoxycarbonyl , 2-Chlor- 2-fluorethoxycarbonyl, 2-Chlor-2 , 2-difluorethoxycarbonyl, 2, 2-Dichlor-2-fluorethoxycarbonyl, 2,2, 2-Trichlorethoxycarbo- nyl, Pentafluorethoxycarbonyl, 2-Fluorpropoxycarbonyl, 3-Flu- orpropoxycarbonyl, 2-Chlorpropoxycarbonyl, 3-Chlorpropoxycar- bonyl, 2-Brompropoxycarbonyl, 3-Brompropoxycarbonyl, 2,2-Di- fluorpropoxycarbonyl, 2, 3-Difluorpropoxycarbonyl, 2,3-Di- chlorpropoxycarbonyl , 3, 3, 3-Trifluorpropoxycarbonyl,Cχ-C 4 haloalkoxycarbonyl: a Cχ-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, bromodifluoryl, bromodifluoro 2-fluoroethoxycarbonyl, 2-chloroethoxycarbonyl, 2-bromoethoxycarbonyl, 2-iodoethoxycarbonyl, 2, 2-difluoroethoxycarbonyl, 2,2, 2-trifluoroethoxycarbonyl, 2-chloro-2-fluoroethoxycarbonyl, 2-chloro-2, 2-difluoroethoxycarbonyl, 2,2-dichloro-2-fluoroethoxycarbonyl, 2,2,2-trichloroethoxycarbonyl, pentafluoroethoxycarbonyl, 2-fluoropropoxycarbonyl, 3-fluoropropoxycarbonyl, 2-chloropropoxycarbonyl, 3-chloropropoxycarbonyl, 2-bromopropoxycarbonyl, 3-bromopropoxycarbonyl, 2,2-di-fluoropropoxycarbonyl, 2, 3-difluoropropoxycarbonyl, 2,3-dichloropropoxycarbonyl, 3, 3, 3-trifluoropropoxycarbonyl,

3.3, 3-Trichlorpropoxycarbonyl, 2,2,3,3, 3-Pentafluorpropoxycarbonyl, Heptafluorpropoxycarbony1, 1- (Fluormethyl) -2-fluor- ethoxycarbonyl , 1- (Chlormethyl) -2-chlorethoxycarbonyl, 1- (Brommethyl) -2-bromethoxycarbonyl, 4-Fluorbutoxycarbonyl, 4-Chlorbutoxycarbonyl, 4-Brombutoxycarbonyl oder 4-Iodbutoxy- carbonyl ,-3.3, 3-trichloropropoxycarbonyl, 2,2,3,3, 3-pentafluoropropoxycarbonyl, heptafluoropropoxycarbony1, 1- (fluoromethyl) -2-fluoro- ethoxycarbonyl, 1- (chloromethyl) -2-chloroethoxycarbonyl, 1- (bromomethyl) -2-bromoethoxycarbonyl, 4-fluorobutoxycarbonyl, 4-chlorobutoxycarbonyl, 4-bromobutoxycarbonyl or 4-iodobutoxycarbonyl, -

Cx-Cg-Halogenoxycarbonyl: einen Cχ-C4-Halogenoxycarbonylrest wie voranstehend genannt, sowie 5-Fluorpentoxycarbonyl, 5-Chlorpentoxycarbonyl, 5-Brompentoxycarbonyl, 6-Fluorhexoxy- carbonyl , 6 -Chlorhexoxycarbonyl oder 6 -Bromhexoxycarbonyl;Cx-Cg-halooxycarbonyl: a Cχ-C 4 halooxycarbonyl radical as mentioned above, and 5-fluoropentoxycarbonyl, 5-chloropentoxycarbonyl, 5-bromopentoxycarbonyl, 6-fluorohexoxycarbonyl, 6-chlorohexoxycarbonyl or 6-bromhexoxycarbonyl;

(Cχ-C4-Alkyl)carbonyloxy: Acetyloxy, Ethylcarbonyloxy, Propyl- carbonyloxy, 1-Methylethylcarbonyloxy, Butylcarbonyloxy, 1-Methylpropylcarbonyloxy, 2-Methylpropylcarbonyloxy oder 1, 1-Dimethylethylcarbonyloxy;(Cχ-C 4 alkyl) carbonyloxy: acetyloxy, ethylcarbonyloxy, propylcarbonyloxy, 1-methylethylcarbonyloxy, butylcarbonyloxy, 1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy or 1, 1-dimethylethylcarbonyloxy;

(Cχ-C4-Alkylamino) carbonyl : z.B. Methylaminocarbonyl, Ethyl- aminocarbonyl, Propylaminocarbonyl, 1-Methylethylaminocarbo- nyl, Butylaminocarbonyl, 1-Methylpropylaminocarbonyl, 2-Me- thylpropylaminocarbonyl oder 1, 1-Dimethylethylaminocarbonyl;(Cχ-C 4 -alkylamino) carbonyl: for example methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl, 1-methylethylaminocarbonyl, butylaminocarbonyl, 1-methylpropylaminocarbonyl, 2-methylpropylaminocarbonyl or 1, 1-dimethylethylaminocarbonyl;

(Cχ-C6-Alkylamino) carbonyl : (Cχ-C4-Alkylamino) carbonyl, wie vorstehend genannt, sowie z.B. Pentylaminocarbonyl, 1-Methyl - butylaminocarbonyl, 2-Methylbutylaminocarbonyl, 3-Methylbu- tylaminocarbonyl, 2, 2-Dimethylpropylaminocarbonyl, 1-Ethyl- propylaminocarbonyl, Hexylaminocarbonyl, 1, 1-Dimethylpropyla- minocarbonyl , 1, 2-Dimethylpropylaminocarbonyl, 1-Methylpen- tylaminocarbonyl , 2-Methylpentylaminocarbonyl, 3-Methylpenty- laminocarbonyl , 4-Methylpentylaminocarbonyl, 1, 1-Dimethyl- butylaminocarbonyl , 1, 2-Dimethylbutylaminocarbonyl, 1,3-Di- methylbutylaminocarbonyl, 2 , 2-Dimethylbutylaminocarbonyl,(Cχ-C 6 -alkylamino) carbonyl: (Cχ-C 4 -alkylamino) carbonyl, as mentioned above, and for example pentylaminocarbonyl, 1-methylbutylaminocarbonyl, 2-methylbutylaminocarbonyl, 3-methylbutylaminocarbonyl, 2, 2-dimethylpropylaminocarbonyl, 1-ethyl-propylaminocarbonyl, hexylaminocarbonyl, 1, 1-dimethylpropylaaminocarbonyl, 1, 2-dimethylpropylaminocarbonyl, 1-methylpentylaminocarbonyl, 2-methylpentylaminocarbonyl, 3-methylpentylaminocarbonyl, 4-methylpentylaminocarbonyl, 1, 1-dimethyl 1, 2-dimethylbutylaminocarbonyl, 1,3-dimethylbutylaminocarbonyl, 2, 2-dimethylbutylaminocarbonyl,

2, 3-Dimethylbutylaminocarbonyl, 3, 3-Dimethylbutylaminocarbo- nyl, 1-Ethylbutylaminocarbonyl, 2-Ethylbutylaminocarbonyl, 1,1, 2-Trimethylpropylaminocarbonyl, 1, 2, 2-Trimethylpropylami- nocarbonyl, 1-Ethyl-l-methylpropylaminocarbonyl oder l-Ethyl-2-methylpropylaminocarbonyl;2, 3-dimethylbutylaminocarbonyl, 3, 3-dimethylbutylaminocarbonyl, 1-ethylbutylaminocarbonyl, 2-ethylbutylaminocarbonyl, 1,1, 2-trimethylpropylaminocarbonyl, 1, 2, 2-trimethylpropylaminocarbonyl, 1-ethyl-l-methyl-propylamine Ethyl 2-methylpropylaminocarbonyl;

Di- (Cχ-C4-alkyl) -aminocarbonyl: z.B. N,N-Dimethylaminocarbo- nyl, N,N-Diethylaminocarbonyl, N,N-Di- (1-methylethyl) aminocarbonyl, N,N-Dipropylaminocarbonyl, N,N-Dibutylaminocarbo- nyl, N,N-Di- (1-methylpropyl) -aminocarbonyl, N,N-Di- (2-methylpropyl) -aminocarbonyl, N,N-Di- (1, 1-dimethylethyl) -aminocarbonyl, N-Ethyl-N-methylaminocarbonyl, N-Methyl-N-propyla- minocarbonyl , N-Methyl-N- (1-methylethyl) -aminocarbonyl, N-Bu- tyl-N-methylaminocarbonyl, N-Methyl-N- (1-methylpropyl) -amino■ carbonyl , N-Methyl-N- (2-methylpropyl) -aminocarbonyl,Di- (Cχ-C 4 -alkyl) -aminocarbonyl: for example N, N-dimethylaminocarbonyl, N, N-diethylaminocarbonyl, N, N-di- (1-methylethyl) aminocarbonyl, N, N-dipropylaminocarbonyl, N, N -Dibutylaminocarbonyl, N, N-di- (1-methylpropyl) -aminocarbonyl, N, N-di- (2-methylpropyl) -aminocarbonyl, N, N-di- (1, 1-dimethylethyl) -aminocarbonyl, N -Ethyl-N-methylaminocarbonyl, N-methyl-N-propyla-minocarbonyl, N-methyl-N- (1-methylethyl) -aminocarbonyl, N-butyl-N-methylaminocarbonyl, N-methyl-N- (1- methylpropyl) amino ■ carbonyl, N-methyl-N- (2-methylpropyl) aminocarbonyl,

N- (1 , 1-Dimethylethyl) -N-methylaminocarbonyl, N-Ethyl-N-pro- pylaminocarbonyl , N-Ethyl-N- (1-methylethyl) -aminocarbonyl, N-Butyl-N-ethylaminocarbonyl, N-Ethyl-N- (1-methylpropyl) - aminocarbonyl, N-Ethyl-N- (2-methyIpropyl) -aminocarbonyl, N- Ethyl-N- (1 , 1-dimethylethyl ) -aminocarbonyl , N- ( 1-Methyl - ethyl) -N-propylaminocarbonyl , N-Butyl-N-propylaminocarbonyl , N- (1-Methylpropyl) -N-propylaminocarbonyl, N-(2-Methyl- propyl) -N-propylaminocarbonyl, N- (1, 1-Dimethylethyl) -N-propylaminocarbonyl, N-Butyl-N- (1-methylethyl) -aminocarbonyl, N- (1-Methylethyl) -N- (1-methylpropyl) -aminocarbonyl, N- (l-Methylethyl)-N- (2-methylpropyl) -aminocarbonyl, N- (1, 1-Dimethylethyl) -N- (1-methylethyl) -aminocarbonyl, N-Butyl-N- (1-methylpropyl) -aminocarbonyl, N-Butyl-N- (2-methyl- propyl) -aminocarbonyl, N-Butyl-N- (1, 1-dimethylethyl) -aminocarbonyl, N- (1-Methylpropyl) -N- (2-methylpropyl) -aminocarbonyl , N- ( 1, 1-Dimethylethyl) -N- ( 1-methylpropyl) -amino- carbonyl oder N- (1, 1-Dimethylethyl) -N- (2-methylpropyl) -aminocarbonyl ;N- (1, 1-dimethylethyl) -N-methylaminocarbonyl, N-ethyl-N-propylaminocarbonyl, N-ethyl-N- (1-methylethyl) aminocarbonyl, N-butyl-N-ethylaminocarbonyl, N-ethyl-N- (1-methylpropyl) - aminocarbonyl, N-ethyl-N- (2-methylpropyl) aminocarbonyl, N-ethyl-N- (1, 1-dimethylethyl) - aminocarbonyl, N- (1-methyl-ethyl) -N-propylaminocarbonyl, N-butyl-N-propylaminocarbonyl, N- (1-methylpropyl) -N-propylaminocarbonyl, N- (2-methylpropyl) -N-propylaminocarbonyl, N- (1, 1-dimethylethyl) -N-propylaminocarbonyl, N-butyl-N- (1-methylethyl) aminocarbonyl, N- (1-methylethyl) -N- (1-methylpropyl) aminocarbonyl, N- (l -Methylethyl) -N- (2-methylpropyl) aminocarbonyl, N- (1, 1-dimethylethyl) -N- (1-methylethyl) aminocarbonyl, N-butyl-N- (1-methylpropyl) aminocarbonyl, N- Butyl-N- (2-methylpropyl) aminocarbonyl, N-butyl-N- (1,1-dimethylethyl) aminocarbonyl, N- (1-methylpropyl) -N- (2-methylpropyl) aminocarbonyl, N- (1, 1-dimethylethyl) -N- (1-methylpropyl) aminocarbonyl or N- (1, 1-dimethylethyl) -N- (2-methylpropyl) aminocarbonyl;

Di- (Cχ-C6~alkyl) -aminocarbonyl: Di- (Cχ-C4-alkyl) -aminocarbonyl, wie voranstehend genannt, sowie z.B. 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-dimethyIpropyl) -aminocarbonyl, N-Methyl-N- (1-ethyl- propyl) -aminocarbonyl, N-Methyl-N-hexylaminocarbonyl, N-Me- thyl-N- (1 , 1-dimethylpropyl ) -aminocarbonyl , N-Methyl-N-Di- (Cχ-C 6 ~ alkyl) -aminocarbonyl: Di- (Cχ-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-dimethyl-propyl) -aminocarbonyl, N- Methyl-N- (1-ethyl-propyl) -aminocarbonyl, N-methyl-N-hexylaminocarbonyl, N-methyl-N- (1, 1-dimethylpropyl) -aminocarbonyl, N-methyl-N-

(1, 2-dimethyIpropyl) -aminocarbonyl, N-Methyl-N- (1-methyl - pentyl) -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-dimethylbutyl) -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-ethyl - butyl) -aminocarbonyl, N-Methyl-N- (2-ethylbutyl) -aminocarbonyl, N-Methyl-N- (1, 1, 2-trimethylpropyl) -aminocarbonyl, N-Methyl-N- (1,2, 2-trimethyIpropyl) -aminocarbonyl, N-Methyl- N- (1-ethyl-l-methyIpropyl) -aminocarbonyl , N-Methyl-N- (1- ethyl-2-methylpropyl) -aminocarbonyl, N-Ethyl-N-pentylamino- carbonyl, N-Ethyl-N- (1-methylbutyl) -aminocarbonyl, N-Ethyl- N- (2-methylbutyl) -aminocarbonyl, N-Ethyl-N- (3-methylbutyl) - aminocarbonyl, N-Ethyl-N- (2 ,2-dimethyIpropyl) -aminocarbonyl, N-Ethyl-N- (1-ethylpropyl) -aminocarbonyl, N-Ethyl-N-hexylami- nocarbonyl, N-Ethyl-N- (1, 1-dimethyIpropyl) -aminocarbonyl, N- Ethyl-N- (1,2-dimethyIpropyl) -aminocarbonyl, N-Ethyl-N-(1, 2-dimethylpropyl) aminocarbonyl, N-methyl-N- (1-methyl-pentyl) -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-dimethylbutyl) -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-trimethyIpropyl) aminocarbonyl, N-methyl- N- (1-ethyl-l-methyIpropyl) aminocarbonyl, N- Methyl-N- (1-ethyl-2-methylpropyl) aminocarbonyl, N-ethyl-N-pentylamino-carbonyl, N-ethyl-N- (1-methylbutyl) aminocarbonyl, N-ethyl-N- (2-methylbutyl ) -aminocarbonyl, N-ethyl-N- (3-methylbutyl) - aminocarbonyl, N-ethyl-N- (2nd , 2-dimethyl-propyl) -aminocarbonyl, N-ethyl-N- (1-ethyl-propyl) -aminocarbonyl, N-ethyl-N-hexylaminocarbonyl, N-ethyl-N- (1,1-dimethyl-propyl) -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-methylpentyi) -aminocarbonyl, N-Ethyl-N- (1, 1-di- methylbutyl) -aminocarbonyl, N-Ethyl-N- (1, 2-dimethylbutyl) - aminocarbonyl, N-Ethyl-N- (1, 3-dimethylbutyl) -aminocarbonyl, N-Ethyl-N- (2 , 2-dimethylbutyl) -aminocarbonyl, N-Ethyl-N- (2,3- dimethylbutyl) -aminocarbonyl, N-Ethyl-N- (3, 3-dimethylbutyl) - aminocarbonyl, N-Ethyl-N- (1-ethylbutyl) -aminocarbonyl, N- Ethyl-N- (2-ethylbutyl) -aminocarbonyl, N-Ethyl-N- (1, 1, 2-tri- methylpropyl) -aminocarbonyl, N-Ethyl-N- (1,2, 2-trimethyl- propyl) -aminocarbonyl, N-Ethyl-N- (1-ethyl-l-methyl- propyl) -aminocarbonyl, N-Ethyl-N- (l-ethyl-2-methyl- propyl) -aminocarbonyl, N-Propyl-N-pentylaminocarbonyl, N-Butyl-N-pentylaminocarbonyl, N, N-Dipentylaminocarbonyl, N-Propyl-N-hexylaminocarbonyl, N-Butyl-N-hexylaminocarbonyl, N-Pentyl-N-hexylaminocarbonyl oder N,N-Dihexylaminocarbonyl;(1-methylpentyl) aminocarbonyl, N-ethyl-N- (2-methylpentyl) aminocarbonyl, N-ethyl-N- (3-methylpentyl) aminocarbonyl, N- Ethyl-N- (4-methylpentyi) aminocarbonyl, N-ethyl-N- (1, 1-dimethylbutyl) aminocarbonyl, N-ethyl-N- (1, 2-dimethylbutyl) aminocarbonyl, N-ethyl N- (1,3-dimethylbutyl) -aminocarbonyl, N-ethyl-N- (2,2-dimethylbutyl) -aminocarbonyl, N-ethyl-N- (2,3-dimethylbutyl) -aminocarbonyl, N-ethyl-N- (3, 3-dimethylbutyl) aminocarbonyl, N-ethyl-N- (1-ethylbutyl) aminocarbonyl, N-ethyl-N- (2-ethylbutyl) aminocarbonyl, N-ethyl-N- (1, 1, 2 -trimethylpropyl) aminocarbonyl, N-ethyl-N- (1,2,2-trimethylpropyl) aminocarbonyl, N-ethyl-N- (1-ethyl-l-methylpropyl) aminocarbonyl, N- Ethyl-N- (l-ethyl-2-methyl-propyl) -aminocarbonyl, N-propyl-N-pentylaminocarbonyl, N-butyl-N-pentylaminocarbonyl, N, N-dipentylaminocarbonyl, N-propyl-N-hexylaminocarbonyl, N- Butyl-N-hexylaminocarbonyl, N-pentyl-N-hexylaminocarbonyl or N, N-dihexylaminocarbonyl;

Di- (Cχ-C6-alkyl) -aminothiocarbonyl : z.B. N,N-Dimethylamino- thiocarbonyl , N,N-Diethylaminothiocarbonyl, N,N-Di- (1-methylethyl) aminothiocarbonyl, N,N-Dipropylaminothiocarbonyl, N,N-Dibutylaminothiocarbonyl, N,N-Di- (1-methylpropyl) -amino- thiocarbonyl, N,N-Di- (2-methylpropyl) -aminothiocarbonyl,Di- (Cχ-C 6 -alkyl) -aminothiocarbonyl: e.g. N, N-dimethylamino-thiocarbonyl, N, N-diethylaminothiocarbonyl, N, N-di- (1-methylethyl) aminothiocarbonyl, N, N-dipropylaminothiocarbonyl, N, N -Dibutylaminothiocarbonyl, N, N-di- (1-methylpropyl) -amino-thiocarbonyl, N, N-di- (2-methylpropyl) -aminothiocarbonyl,

N,N-Di- (1, 1-dimethylethyl) -aminothiocarbonyl, N-Ethyl-N-me- thylaminothiocarbonyl, N-Methyl-N-propylaminothiocarbonyl, N- Methyl-N- (1-methylethyl) -aminothiocarbonyl, N-Butyl-N-methyl- aminothiocarbonyl, N-Methyl-N- (1-methylpropyl) -aminothio- carbonyl, N-Methyl-N- (2-methyIpropyl) -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-methyIpropyl) -aminothiocarbonyl, N-Ethyl-N- (2-me- thylpropyl) -aminothiocarbonyl, N-Ethyl-N- (1, 1-dimethyl - ethyl) -aminothiocarbonyl , N- (1-Methylethyl) -N-propylamino- thiocarbonyl, N-Butyl-N-propylaminothiocarbonyl, N-(1-Methyl- propyl) -N-propylaminothiocarbonyl, N- (2-Methylpropyl) -N-propylaminothiocarbonyl, N- (1, 1-Dimethylethyl) -N-propylamino- thiocarbonyl, 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-methyIpropyl) -aminothiocarbonyl, N-Butyl-N- (2-me- thylpropyl) -aminothiocarbonyl, N-Butyl-N- (1, 1-dimethyl - ethyl) -aminothiocarbonyl, N- (1-Methylpropyl) -N- (2-methyl- propyl) -aminothiocarbonyl, N- (1, 1-Dimethylethyl) -N- (1-methyl - propyl) -aminothiocarbonyl, N- (1, 1-Dimethylethyl) -N- (2-methylpropyl) -aminothiocarbonyl, N-Methyl-N-pentylaminothiocarbo- nyl, N-Methyl-N- (1-methylbutyl) -aminothiocarbonyl, N-Methyl-N- (2-methylbutyl) -aminothiocarbonyl, N-Methyl-N- (3-methylbutyl) -aminothiocarbonyl, N-Methyl-N- (2, 2-dimethyl- propyl) -aminothiocarbonyl, N-Methyl-N- (1-ethyIpropyl) -aminothiocarbonyl, N-Methyl-N-hexylaminothiocarbonyl, N-Methyl-N- (1, 1-dimethylpropyl) -aminothiocarbonyl, N-Methyl- N- (1, 2-dimethyIpropyl) -aminothiocarbonyl, N-Methyl-N- (1-methylpentyl) -aminothiocarbonyl, N-Methyl-N- (2-methyl - pentyl) -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-1-methyIpropyl) -aminothiocarbonyl, N-Methyl-N- (1-ethyl- 2-methylpropyl) -aminothiocarbonyl, N-Ethy1-N-pentylaminothio- carbonyl , N-Ethyl-N- ( 1-methylbutyl) -aminothiocarbonyl , N- Ethyl-N- (2-methylbutyl) -aminothiocarbonyl, N-Ethyl-N- (3- methylbutyl) -aminothiocarbonyl, N-Ethyl-N- (2 , 2-dimethyl- propyl) -aminothiocarbonyl, N-Ethyl-N- (1-ethylpropyl) -aminothiocarbonyl, N-Ethyl-N-hexylaminothiocarbonyl, N-Ethyl-N- (1, 1-dimethyIpropyl) -aminothiocarbonyl, N-Ethyl-N- (1,2- dimethylpropyl) -aminothiocarbonyl, N-Ethyl-N- (1-methyl - pentyl) -aminothiocarbonyl, N-Ethyl-N- (2-methylpentyl) -amino- thiocarbonyl, 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-dimethyl- butyl) -aminothiocarbonyl, N-Ethyl-N- (2, 2-dimethylbutyl) - aminothiocarbonyl, N-Ethyl-N- (2, 3-dimethylbutyl) -aminothiocarbonyl, N-Ethyl-N- (3 , 3-dimethylbutyl) -aminothiocarbonyl, 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-trimethyl- propyl) -aminothiocarbonyl, N-Ethyl-N- (1-ethyl-1-methylpropyl) -aminothiocarbonyl, N-Ethyl-N- (l-ethyl-2-methyl- propyl) -aminothiocarbonyl, N-Propyl-N-pentylaminothiocarbo- nyl, N-Butyl-N-pentylaminothiocarbonyl, N,N-Dipentylamino- thiocarbonyl , N-Propyl-N-hexylaminothiocarbonyl, N-Butyl- N-hexylaminothiocarbonyl , N-Pentyl-N-hexylaminothiocarbonyl oder N,N-Dihexylaminothiocarbonyl;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) -aminothio-carbonyl, 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-dimethyl-ethyl) -aminothiocarbonyl, N- (1-methylethyl) -N-propylamino-thiocarbonyl, N-butyl-N- propylaminothiocarbonyl, N- (1-methylpropyl) -N-propylaminothiocarbonyl, N- (2-methylpropyl) -N-propylaminothiocarbonyl, N- (1, 1-dimethylethyl) -N-propylamino-thiocarbonyl, 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-me- thylpropyl) aminothiocarbonyl, N-butyl-N- (1, 1-dimethyl-ethyl) -aminothiocarbonyl, N- (1-methylpropyl) -N- (2-methyl-propyl) -aminothiocarbonyl, N- (1, 1- Dimethylethyl) -N- (1-methyl-propyl) -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-dimethyl- propyl) aminothiocarbonyl, N-methyl-N- (1-ethyIpropyl) aminothiocarbonyl, N-methyl-N-hexylaminothiocarbonyl, N-methyl-N- (1, 1-dimethylpropyl) aminothiocarbonyl, N-methyl- N- ( 1,2-dimethyl-propyl) -aminothiocarbonyl, N-methyl-N- (1-methylpentyl) -aminothiocarbonyl, N-methyl-N- (2-methyl-pentyl) -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-1-methylpropyl) -a minothiocarbonyl, N-methyl-N- (1-ethyl-2-methylpropyl) aminothiocarbonyl, N-Ethy1-N-pentylaminothio-carbonyl, 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- (1, 1-dimethyIpropyl) -aminothiocarbonyl, N-ethyl-N- (1,2-dimethylpropyl) -aminothiocarbonyl, N-ethyl-N- (1-methyl-pentyl) aminothiocarbonyl, N-ethyl-N- (2-methylpentyl) amino-thiocarbonyl, 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-dimethylbutyl) - amine othiocarbonyl, 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-trimethyl-propyl) -aminothiocarbonyl, N-ethyl-N- (1-ethyl-1-methylpropyl) -aminothiocarbonyl, N-ethyl-N- (l-ethyl-2-methyl - propyl) aminothiocarbonyl, N-propyl-N-pentylaminothiocarbonyl, N-butyl-N-pentylaminothiocarbonyl, N, N-dipentylamino-thiocarbonyl, N-propyl-N-hexylaminothiocarbonyl, N-butyl-N-hexylaminothiocarbonyl, Pentyl-N-hexylaminothiocarbonyl or N, N-dihexylaminothiocarbonyl;

Cχ-C4-Alkoxy-Cχ-C4-alkoxy, sowie die Alkoxyalkoxyteile von Cχ-C4-Alkoxy-Cχ-C4-alkoxycarbonyl : durch Cχ-C4-Alkoxy, wie vorstehend genannt, substituiertes Cχ-C4-Alkoxy, also z.B. für Methoxymethoxy, Ethoxymethoxy, Propoxymethoxy, (1-Methyl- ethoxy)methoxy, Butoxymethoxy, (l-Methylpropoxy)methoxy, (2-Methylpropoxy)methoxy, (1, 1-Dimethylethoxy) methoxy, 2- (Methoxy) ethoxy, 2- (Ethoxy) ethoxy, 2- (Propoxy) ethoxy, 2- (1-Methylethoxy) ethoxy, 2- (Butoxy) ethoxy, 2-(l-Methyl- propoxy) ethoxy, 2- (2-Methylpropoxy) ethoxy, 2- (1, 1-Dimethyl- ethoxy) ethoxy, 2- (Methoxy) propoxy, 2- (Ethoxy) propoxy, 2- (Propoxy)propoxy, 2- (1-Methylethoxy)propoxy, 2- (Butoxy) -propoxy, 2- (1-Methylpropoxy) propoxy, 2-(2-Methyl- propoxy) ropoxy, 2- (1, i-Dimethylethoxy) propoxy,Cχ-C 4 -alkoxy-Cχ-C 4 -alkoxy, and the alkoxyalkoxy parts of Cχ-C 4 -alkoxy-Cχ-C 4 -alkoxycarbonyl: Cχ-C 4 -alkoxy, as mentioned above, substituted Cχ-C 4 - Alkoxy, for example for Methoxymethoxy, ethoxymethoxy, propoxymethoxy, (1-methylethoxy) methoxy, butoxymethoxy, (l-methylpropoxy) methoxy, (2-methylpropoxy) methoxy, (1, 1-dimethylethoxy) methoxy, 2- (methoxy) ethoxy, 2- ( Ethoxy) ethoxy, 2- (propoxy) ethoxy, 2- (1-methylethoxy) ethoxy, 2- (butoxy) ethoxy, 2- (l-methylpropoxy) ethoxy, 2- (2-methylpropoxy) ethoxy, 2- ( 1, 1-dimethylethoxy) ethoxy, 2- (methoxy) propoxy, 2- (ethoxy) propoxy, 2- (propoxy) propoxy, 2- (1-methylethoxy) propoxy, 2- (butoxy) propoxy, 2- (1-methylpropoxy) propoxy, 2- (2-methylpropoxy) ropoxy, 2- (1, i-dimethylethoxy) propoxy,

3- (Methoxy) -propoxy, 3- (Ethoxy) propoxy, 3- (Propoxy) propoxy, 3- (1-Methylethoxy) propoxy, 3- (Butoxy) propoxy, 3-(l-Methyl- propoxy) -propoxy, 3- (2-Methylpropoxy) propoxy, 3- (1, 1-Dimethylethoxy) propoxy, 2- (Methoxy)butoxy, 2- (Ethoxy)butoxy, 2- (Propoxy)butoxy, 2-(l-Methyl- ethoxy)butoxy, 2- (Butoxy) -butoxy, 2- (1-Methylpropoxy)butoxy, 2- (2-Methylpropoxy)butoxy, 2- (1, 1-Dimethylethoxy) butoxy, 3- (Methoxy)butoxy, 3- (Ethoxy) -butoxy, 3- (Propoxy) butoxy, 3- (1-Methylethoxy) butoxy, 3- (Butoxy)butoxy, 3-(l-Methyl- propoxy) butoxy, 3- (2-Methylpropoxy) butoxy, 3- (1, 1-Dimethyl- ethoxy)butoxy, 4- (Methoxy) -butoxy, 4- (Ethoxy)butoxy, 4- (Propoxy)butoxy, 4- (1-Methylethoxy)butoxy, 4- (Butoxy)butoxy, 4- (1-Methylpropoxy) butoxy, 4-(2-Methyl- propoxy)butoxy oder 4- (1, 1-Dimethylethoxy)butoxy;3- (methoxy) propoxy, 3- (ethoxy) propoxy, 3- (propoxy) propoxy, 3- (1-methylethoxy) propoxy, 3- (butoxy) propoxy, 3- (l-methylprooxy) propoxy, 3- (2-methylpropoxy) propoxy, 3- (1, 1-dimethylethoxy) propoxy, 2- (methoxy) butoxy, 2- (ethoxy) butoxy, 2- (propoxy) butoxy, 2- (l-methylethoxy) butoxy, 2- (butoxy) butoxy, 2- (1-methylpropoxy) butoxy, 2- (2-methylpropoxy) butoxy, 2- (1, 1-dimethylethoxy) butoxy, 3- (methoxy) butoxy, 3- (ethoxy ) -butoxy, 3- (propoxy) butoxy, 3- (1-methylethoxy) butoxy, 3- (butoxy) butoxy, 3- (l-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;

C3-C6-Alkenyl, sowie die Alkenylteile von C3-C6-Alkenyl- carbonyl, C3-C6-Alkenyloxy, C3-C6-Alkenyloxycarbonyl, C3-C6-Alkenylaminocarbonyl, N- (C3-C6-Alkenyl) -N- (Cχ-C6) alkylaminocarbonyl, N- (C3-C6-Alkenyl) -N- (Cχ-C6-alkoxy) amino- carbonyl: z.B. Prop-2-en-l-yl, But-l-en-4-yl, 1-Methyl- prop-2-en-l-yl, 2-Methyl-prop-2-en-l-yl, 2-Buten-l-yl, l-Penten-3-yl, l-Penten-4-yl, 2-Penten-4-yl, 1-Methyl- but-2-en-l-yl, 2-Methyl-but-2-en-l-yl, 3-Methyl- but-2-en-l-yl, l-Methyl-but-3-en-l-yl, 2-Methyl- but-3-en-l-yl, 3-Methyl-but-3-en-l-yl, 1, 1-Dimethyl- prop-2-en-l-yl, 1, 2-Dimethyl-prop-2-en-l-yl, 1-Ethyl- prop-2-en-l-yl, Hex-3-en-l-yl, Hex-4-en-l-yl, Hex-5-en-l-yl, l-Methyl-pent-3-en-l-yl, 2-Methyl-pent-3-en-l-yl, 3-Methyl- pent-3-en-l-yl, 4-Methyl-pent-3-en-l-yl, 1-Methyl- pent-4-en-l-yl, 2-Methyl-pent-4-en-l-yl, 3-Methyl- pent-4-en-l-yl, 4-Methyl-pent-4-en-l-yl, 1, 1-Dimethyl- but-2-en-l-yl, 1, l-Dimethyl-but-3-en-l-yl, 1, 2-Dimethyl- but-2-en-l-yl, 1, 2-Dimethyl-but-3-en-l-yl, 1, 3-Dimethyl- but-2-en-l-yl, 1, 3-Dimethyl-but-3-en-l-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-yl, l-Ethyl-but-3-en-l-yl, 2-Ethyl-but-2-en-l-yl, 2-Ethyl-but-3-en-l-yl , 1 , 1 , 2-Trimethyl-prop-2-en-l-yl , l-Ethyl-l-methyl-prop-2-en-l-yl oder l-Ethyl-2-methyl- prop-2-en-l-yl ;C 3 -C 6 alkenyl, and the alkenyl parts of C 3 -C 6 alkenylcarbonyl, C 3 -C 6 alkenyloxy, C 3 -C 6 alkenyloxycarbonyl, C 3 -C 6 alkenylaminocarbonyl, N- (C 3 -C 6 -Alkenyl) -N- (Cχ-C 6 ) alkylaminocarbonyl, N- (C 3 -C 6 -alkenyl) -N- (Cχ-C 6 -alkoxy) aminocarbonyl: eg prop-2-ene -l-yl, but-l-en-4-yl, 1-methyl-prop-2-en-l-yl, 2-methyl-prop-2-en-l-yl, 2-butene-l-yl , l-penten-3-yl, l-penten-4-yl, 2-penten-4-yl, 1-methyl-but-2-en-l-yl, 2-methyl-but-2-en-l -yl, 3-methyl-but-2-en-l-yl, l-methyl-but-3-en-l-yl, 2-methyl-but-3-en-l-yl, 3-methyl-but -3-en-1-yl, 1, 1-dimethyl-prop-2-en-1-yl, 1, 2-dimethyl-prop-2-en-1-yl, 1-ethyl-prop-2-ene -l-yl, hex-3-en-l-yl, hex-4-en-l-yl, hex-5-en-l-yl, l-methyl-pent-3-en-l-yl, 2 -Methyl-pent-3-en-l-yl, 3-methyl-pent-3-en-l-yl, 4-methyl-pent-3-en-l-yl, 1-methyl-pent-4-ene -l-yl, 2-methyl-pent-4-en-l-yl, 3-methyl-pent-4-en-l-yl, 4-methyl-pent-4-en-l-yl, 1, 1 -Dimethyl-but-2-en-1-yl, 1, l-dimethyl-but-3-en-1-yl, 1, 2-dimethyl-but-2-en-1-yl, 1, 2-di methyl-but-3-en-l-yl, 1, 3-dimethyl-but-2-en-l-yl, 1, 3-dimethyl-but-3-en-l-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-yl, l-ethyl-but-3-en-l-yl, 2-ethyl-but-2-en-l-yl, 2-ethyl-but-3-en-1-yl, 1, 1, 2-trimethyl-prop-2-en-1-yl, 1-ethyl-1-methyl-prop-2-en-1-yl or l-ethyl-2-methyl-prop-2-en-l-yl;

- C-C6-Alkenyl, sowie die Alkenylteile von C2-Ce-Alkenyl- carbonyl, Phenyl-C2-C6-alkenylcarbonyl und Heterocyclyl- C-C6-alkenylcarbonyl: C3-C6-Alkenyl, wie voranstehend genannt, sowie Ethenyl;- CC 6 -alkenyl, and the alkenyl parts of C 2 -C e -alkenylcarbonyl, phenyl-C 2 -C 6 -alkenylcarbonyl and heterocyclyl-CC 6 -alkenylcarbonyl: C 3 -C6-alkenyl, as mentioned above, and 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, 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;- 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-trichlorallyl, 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 C3-Cg-Alkinyl- carbonyl, C3-C6-Alkinyloxy, C3-C6-Alkinyloxycarbony, C3-C6-Al- kinylaminocarbonyl, N- (C3-C6-Alkinyl) -N- (Cχ-C6- alkyl) -aminocarbonyl, N- (C3-C6-Alkinyl) -N- (Cχ-C6-alkoxy- aminocarbonyl : z.B. Propargyl, But-l-in-3-yl, But-l-in-4-yl, But-2-in-l-yl, Pent-l-in-3-yl, Pent-l-in-4-yl, Pent-1-in- 5-yl, Pent-2-in-l-yl, Pent-2-in-4-yl, Pent-2-in-5-yl, 3-Me- thyl-but-l-in-3-yl, 3-Methyl-but-l-in-4-yl, Hex-l-in-3- yl, Hex-l-in-4-yl, Hex-l-in-5-yl, Hex-l-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-pent-l-in-3-yl, 3-Methyl-pent- l-in-4-yl, 3-Methyl-pent-l-in-5-yl, 4-Methyl-pent-2-in-4-yl oder 4-Methyl-pent-2-in-5-yl;C 3 -C 6 alkynyl, and the alkynyl parts of C 3 -Cg alkynylcarbonyl, C 3 -C 6 alkynyloxy, C 3 -C 6 alkynyloxycarbonyl, C 3 -C 6 alkynylaminocarbonyl, N- ( C 3 -C 6 alkynyl) -N- (Cχ-C 6 - alkyl) aminocarbonyl, N- (C 3 -C 6 -alkynyl) -N- (Cχ-C6 alkoxy aminocarbonyl: for example, propargyl, but- l-in-3-yl, but-l-in-4-yl, but-2-in-l-yl, pent-l-in-3-yl, pent-l-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-but-l-in 3-yl, 3-methyl-but-l-in-4-yl, hex-l-in-3-yl, hex-l-in-4-yl, hex-l-in-5-yl, hex l-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-pent-1-in-3-yl, 3-methyl-pent-1-in-4-yl, 3-methyl pent-l-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 -Ce-Alkinyl- carbonyl : C3-C6-Alkinyl, wie voranstehend genannt, sowie Ethinyl;C 2 -C 6 alkynyl, and the alkynyl parts of C -Ce 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-l-yl, 3-Iod-prop-2-in-l-yl, 4-Fluorbut-2-in-l-yl, 4-Chlorbut-2-in-l-yl, 1, 1-Difluorbut-2-in-l-yl, 4-Iod- but-3-in-l-yl, 5-Fluorpent-3-in-l-yl, 5-Iod-pent-4-in-l-yl, 6-Fluor-hex-4-in-l-yl oder 6-Iod-hex-5-in-l-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, for example 1,1-difluoroprop-2- in-l-yl, 3-iodo-prop-2-in-l-yl, 4-fluorobut-2-in-l-yl, 4-chlorobut-2-in-l-yl, 1, 1-difluorobut- 2-in-l-yl, 4-iodobut-3-in-l-yl, 5-fluoropent-3-in-l-yl, 5-iodo-pent-4-in-l-yl, 6- Fluoro-hex-4-in-1-yl or 6-iodo-hex-5-in-1-yl;

C3-C6-Cycloalkyl, sowie die Cycloalkylteile von C3-C6-Cyclo- alkylcarbonyl: z.B. Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl ; Heterocyclyl, sowie Heterocyclylteile von Heterocyclylcarbonyl, Heterocyclyl-Cχ-C6-alkyl, Heterocyclyloxycarbonyl, Heterocyclyloxythiocarbonyl , Heterocyclylcarbonyl-Cχ-C6-alkyl, N- (Cχ-C6-Alkyl) -N- (heterocyclyl) -aminocarbonyl, Heterocyclyl - aminocarbonyl: ein gesättigter, partiell gesättigter oder un- gesättiger 5- oder 6-gliedriger, C-gebundener, hetero- cyclischer Ring, der ein bis vier gleiche oder verschiedene Heteroatome, ausgewählt aus folgender Gruppe: Sauerstoff, Schwefel oder Stickstoff, enthält, also z.B. 5-gliedrige Ringe wie:C 3 -C 6 cycloalkyl, and the cycloalkyl parts of C 3 -C 6 cycloalkylcarbonyl: for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl; Heterocyclyl, and also heterocyclyl parts of heterocyclylcarbonyl, heterocyclyl-Cχ-C 6 -alkyl, heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl, heterocyclylcarbonyl-Cχ-C 6 -alkyl, N- (Cχ-C 6 -alkylcyl) -lyl-, - aminocarbonyl: a saturated, partially saturated or unsaturated 5- or 6-membered, C-linked, heterocyclic ring which contains one to four identical or different heteroatoms, selected from the following group: oxygen, sulfur or nitrogen, ie e.g. 5-link rings such as:

Tetrahydrofuran-2-yl, Tetrahydrofuran-3-yl, Tetrahydrothien- 2-yl, Tetrahydrothien-3-yl,Tetrahydropyrrol-2-yl, Tetrahydro- pyrrol-3-yl, 2, 3-Dihydrofuran-2-yl, 2 , 3-Dihydrofuran-3-yl, 2, 5-Dihydrofuran-2-yl, 2, 5-Dihydrofuran-3-yl, 4,5-Dihydro- furan-2-yl, 4, 5-Dihydrofuran-3-yl, 2, 3-Dihydrothien-2-yl, 2,3-Dihydrothien-3-yl, 2, 5-Dihydrothien-2-yl, 2,5-Dihydro- thien-3-yl, 4, 5-Dihydrothien-2-yl, 4, 5-Dihydrothien-3-yl,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, 4,5-dihydrofuran-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,

2 , 3-Dihydro-lH-pyrrol-2-yl , 2 , 3-Dihydro-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-dihydro-lH-pyrrol-3-yl, 2,5-dihydro-lH-pyrrol-2-yl, 2,5-dihydro-lH- pyrrol-3-yl,

4 , 5-Dihydro-lH-pyrrol-2-yl , 4 , 5-Dihydro-lH-pyrrol-3-yl ,4,5-dihydro-lH-pyrrol-2-yl, 4,5-dihydro-lH-pyrrol-3-yl,

3, 4-Dihydro-2H-pyrrol-2-yl , 3 , 4-Dihydro-2H-pyrrol-3-yl,3,4-dihydro-2H-pyrrol-2-yl, 3,4-dihydro-2H-pyrrol-3-yl,

3 , 4-Dihydro-5H-pyrrol-2-yl , 3 , -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, Tetrahy- droisoxazol-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, Tetrahydro- imidazol-4-yl, Tetrahydrooxazol-2-yl, Tetrahydrooxazol-4-yl, Tetrahydrooxazol-5-yl, Tetrahydrothiazol-2-yl, Tetrahydro- thiazol-4-yl, Tetrahydrothiazol-5-yl, 1, 3-Dioxolan-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,3, 4-dihydro-5H-pyrrol-2-yl, 3, -dihydro-5H-pyrrol-3-yl, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, pyrrol-2-yl, pyrrole -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 -yl, tetrahydrothiazol-5-yl, 1, 3-dioxolan-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,

4, 5-Dihydro-lH-pyrazol-3-yl, 4, 5-Dihydro-lH-pyrazol-4-yl, 4, 5-Dihydro-lH-pyrazol-5-yl, 2, 5-Dihydro-lH-pyrazol-3-yl, 2, 5-Dihydro-lH-pyrazol-4-yl, 2, 5-Dihydro-lH-pyrazol-5-yl,4,5-dihydro-lH-pyrazol-3-yl, 4,5-dihydro-lH-pyrazol-4-yl, 4,5-dihydro-lH-pyrazol-5-yl, 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-Dihy- droisoxazol-5-yl, 2, 5-Dihydroisoxazol-3-yl, 2, 5-Dihydroisoxa- zol-4-yl, 2, 5-Dihydroisoxazol-5-yl, 2, 3-Dihydroisoxazol-3-yl, 2, 3-Dihydroisoxazol-4-yl, 2, 3-Dihydroisoxazol-5-yl, 4,5-Dihy- droisothiazol-3-yl, 4 , 5-Dihydroisothiazol-4-yl, 4,5-Dihydro- isothiazol-5-yl, 2, 5-Dihydroisothiazol-3-yl, 2, 5-Dihydroiso- thiazol-4-yl, 2, 5-Dihydroisothiazol-5-yl, 2, 3-Dihydroisothia- zol-3-yl, 2, 3-Dihydroisothiazol-4-yl, 2 , 3-Dihydroisothiazol- 5-yl, Δ3-l,2-Dithiol-3-yl, Δ3-l, 2-Dithiol-4-yl, Δ3-1,2-Di- thiol-5-yl, 4, 5-Dihydro-lH-imidazol-2-yl, 4 , 5-Dihydro-lH-imi- dazol-4-yl, 4, 5-Dihydro-lH-imidazol-5-yl, 2 , 5-Dihydro-lH-imi- dazol-2-yl, 2, 5-Dihydro-lH-imidazol-4-yl, 2 , 5-Dihydro-lH-imi- dazol-5-yl, 2, 3-Dihydro-lH-imidazol-2-yl, 2 , 3-Dihydro-lH-imi- dazol-4-yl, 4 , 5-Dihydrooxazol-2-yl, 4, 5-Dihydrooxazol-4-yl, 4, 5-Dihydrooxazol-5-yl, 2 , 5-Dihydrooxazol-2-yl, 2,5-Dihydro- oxazol-4-yl, 2, 5-Dihydrooxazol-5-yl, 2, 3-Dihydrooxazol-2-yl, 2, 3-Dihydrooxazol-4-yl, 2 , 3-Dihydrooxazol-5-yl, 4,5-Dihydro- thiazol-2-yl, 4 , 5-Dihydrothiazol-4-yl, 4 , 5-Dihydrothia- zol-5-yl, 2, 5-Dihydrothiazol-2-yl, 2, 5-Dihydrothiazol-4-yl, 2, 5-Dihydrothiazol-5-yl, 2, 3-Dihydrothiazol-2-yl, 2,3-Dihy- drothiazol-4-yl, 2, 3-Dihydrothiazol-5-yl, 1, 3-Dioxol-2-yl, l,3-Dioxol-4-yl, 1, 3-Dithiol-2-yl, 1 , 3-Dithiol-4-yl, 1,3-Oxa- thiol-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-Δ-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-Δ-Thiadiazolin-3-yl, 1, 2, 4-Δ4-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, 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 , l,2,4-Δ3-Triazolin-5-yl, 1, 2, 4-Δi-Triazolin-2-yl, 1,2,4-Tri- azolin-3-yl, 3H-1, 2 , 4-Dithiazol-5-yl, 2H-1, 3, 4-Dithiazol-5- yi, 2H-l,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, l,2,3-Thiadiazol-4-yl, 1, 2, 3-Thiadiazol-5-yl, l,2,4-Thiadiazol-3-yl, 1, 2, 4-Thiadiazol-5-yl, 1,3,4-Thia- diazolyl-2-yl, 1, 2, 3-Triazol-4-yl, 1, 2,4-Triazol-3-yl, Tetrazol-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-dihy- droisothiazol-3-yl, 4,5-dihydroisothiazol-4-yl, 4,5-dihydro-isothiazol-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 3 -l, 2-dithiol -3-yl, Δ 3 -l, 2-dithiol-4-yl, Δ 3 -1,2-di- thiol-5-yl, 4,5-dihydro-lH-imidazol-2-yl, 4,5-dihydro-lH-imidazol-4-yl, 4,5-dihydro-lH-imidazol-5-yl, 2,5-dihydro-lH-imidazol-2-yl, 2,5-dihydro-lH-imidazol-4-yl, 2,5-dihydro-lH-imidazol-5-yl, 2,3- Dihydro-lH-imidazol-2-yl, 2,3-dihydro-lH-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-dihydro-thiazol-2-yl, 4,5-dihydrothiazol-4-yl, 4,5-dihydrothiazol-5- yl, 2,5-dihydrothiazol-2-yl, 2,5-dihydrothiazol-4-yl, 2,5-dihydrothiazol-5-yl, 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, 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, pyrazol-3-yl, pyrazol-4-yl, isoxazole 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-Δ 2 -oxadiazolin-4-yl, 1,2, 3-Δ 2 -oxadiazolin-5-yl, l, 2,4-Δ-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, l, 2,4-Δ-thiadiazolin-3-yl, 1, 2, 4-Δ 4 -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 -Thiadiazolin-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-thiadiazolin-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, l, 2,4-Δ 3 -triazolin-5-yl, 1, 2, 4-Δ i -triazolin-2-yl, 1,2,4-triazolin-3-yl, 3H-1, 2, 4-dithiazol-5-yl, 2H-1, 3, 4 -Dithiazol-5-yi, 2H-l, 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, l, 2,3-thiadiazol-4-yl, 1,2,3 Thiadiazol-5-yl, l, 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,

6-gliedrige Ringe wie:6-link rings such as:

Tetrahydropyran-2-yl, Tetrahydropyran-3-yl, Tetrahydro- pyran-4-yl, Piperidin-2-yl, Piperidin-3-yl, Piperidin-4-yl, Tetrahydrothiopyran-2-yl, Tetrahydrothiopyran-3-yl, Tetra- hydrothiopyran-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,Tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, tetrahydrothiopyran-2-yl, tetrahydrothiopyran-3-yl, Tetrahedral hydrothiopyran-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-Tetrahydropyridin-3-yl, 1, 2 , 3 , 4-Tetrahydropyri- din-2-yl, 2H-5, 6-Dihydropyran-2-yl, 2H-5, 6-Dihydropyran-3-yl, 2H-5, 6-Dihydropyran-4-yl, 2H-5, 6-Dihydropyran-5-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-tetrahydropyridin-3-yl, 1, 2, 3, 4-tetrahydropyridin-2-yl, 2H-5, 6-dihydropyran-2-yl, 2H-5, 6-dihydropyran-3-yl, 2H-5, 6-dihydropyran-4-yl, 2H-5, 6-dihydropyran-5-yl,

2H-5,6-Dihydropyran-6-yl, 2H-5, 6-Dihydrothiopyran-2-yl, 2H-5,6-Dihydrothiopyran-3-yl, 2H-5, β-Dihydrothiopyran-4-yl, 2H-5, 6-Dihydrothiopyran-5-yl , 2H-5, 6-Dihydrothiopyran-6-yl, 1,2,5, 6-Tetrahydropyridin-2-yl, 1,2,5, 6-Tetrahydropyridin-3- yl, l,2,5,6-Tetrahydropyridin-4-yl, 1, 2 , 5, 6-Tetrahydropyri- din-5-yl, 1, 2, 5, 6-Tetrahydropyridin-6-yl, 2, 3 , 4 , 5-Tetrahydro- pyridin-2-yl, 2 , 3, 4, 5-Tetrahydropyridin-3-yl, 2 , 3, 4, 5-Tetra- hydropyridin-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,2H-5,6-dihydropyran-6-yl, 2H-5, 6-dihydrothiopyran-2-yl, 2H-5,6-dihydrothiopyran-3-yl, 2H-5, β-dihydrothiopyran-4-yl, 2H- 5, 6-dihydrothiopyran-5-yl, 2H-5, 6-dihydrothiopyran-6-yl, 1,2,5, 6-tetrahydropyridin-2-yl, 1,2,5, 6-tetrahydropyridin-3-yl, l, 2,5,6-tetrahydropyridin-4-yl, 1, 2, 5, 6-tetrahydropyridin-5-yl, 1, 2, 5, 6-tetrahydropyridin-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-Dihydropyri- din-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-Thiopy- ran-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,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, 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,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,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, l,4-Dioxan-2-yl, 1, 3-Dithian-2-yl, 1, 3-Dithian-4-yl, l,3-Dithian-5-yl, 1, 4-Dithian-2-yl, 1, 3-Oxathian-2-yl, l,3-Oxathian-4-yl, 1, 3-Oxathian-5-yl, 1, 3-Oxathian-6-yl, l,4-Oxathian-2-yl, 1, 4-Oxathian-3-yl, 1, 2-Dithian-3-yl,Pyridin-4-yl, 1, 3-dioxan-2-yl, 1, 3-dioxan-4-yl, 1,3-dioxan-5-yl, l, 4-dioxan-2-yl, 1, 3- Dithian-2-yl, 1,3-dithian-4-yl, 1,3-dithian-5-yl, 1,4-dithian-2-yl, 1,3-oxathian-2-yl, 1,3- Oxathian-4-yl, 1, 3-oxathian-5-yl, 1, 3-oxathian-6-yl, l, 4-oxathian-2-yl, 1, 4-oxathian-3-yl, 1, 2- Dithian-3-yl,

1, 2-Dithian-4-yl, Hexahydropyrimidin-2-yl, Hexahydropyrimi- din-4-yl, Hexahydropyrimidin-5-yl, Hexahydropyrazin-2-yl, Hexahydropyridazin-3-yl, Hexahydropyridazin-4-yl, Tetra- hydro-1, 3-oxazin-2-yl, Tetrahydro-1, 3-oxazin-4-yl, Tetra- hydro-1, 3-oxazin-5-yl, Tetrahydro-1, 3-oxazin-6-yl, Tetra- hydro-1, 3-thiazin-2-yl, Tetrahydro-1, 3-thiazin-4-yl, Tetra- hydro-1, 3-thiazin-5-yl, Tetrahydro-1, 3-thiazin-6-yl, Tetra- hydro-1, 4-thiazin-2-yl, Tetrahydro-1, 4-thiazin-3-yl, Tetra- hydro-1, 4-oxazin-2-yl, Tetrahydro-1, 4-oxazin-3-yl, Tetra- hydro-1, 2-oxazin-3-yl, Tetrahydro-1, 2-oxazin-4-yl, Tetra- hydro-1, 2-oxazin-5-yl, Tetrahydro-1, 2-oxazin-6-yl, 2H-5,6-Di- hydro-1, 2-oxazin-3-yl, 2H-5, 6-Dihydro-l, 2-oxazin-4-yl, 2H-5,6-Dihydro-l,2-oxazin-5-yl, 2H-5, 6-Dihydro-l, 2-oxa- zin-6-yl, 2H-5, 6-Dihydro-l, 2-thiazin-3-yl, 2H-5,6-Di- hydro-1, 2-thiazin-4-yl, 2H-5, 6-Dihydro-l, 2-thiazin-5-yl, 2H-5, 6-Dihydro-l, 2-thiazin-6-yl, 4H-5, 6-Dihydro-l, 2-oxa- zin-3-yl, 4H-5, 6-Dihydro-l, 2-oxazin-4-yl, 4H-5, 6-Dihydro-1, 2-dithian-4-yl, hexahydropyrimidin-2-yl, hexahydropyrimidine-4-yl, hexahydropyrimidin-5-yl, hexahydropyrazin-2-yl, hexahydropyridazin-3-yl, hexahydropyridazin-4-yl, tetra- hydro-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-yl, tetrahydro-1,3-thiazin-4-yl, tetrahydro-1,3-thiazin-5-yl, tetrahydro-1,3-thiazin-6- yl, tetra hydro-1,4-thiazin-2-yl, tetrahydro-1,4-thiazin-3-yl, tetrahydro-1,4-oxazin-2-yl, tetrahydro-1,4-oxazin-3-yl, Tetrahydro-1,2-oxazin-3-yl, tetrahydro-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-l, 2-oxazin-4-yl, 2H-5,6-dihydro-l, 2-oxazin-5-yl, 2H-5, 6-dihydro-l, 2-oxazin-6-yl, 2H-5, 6-dihydro-l, 2-thiazin-3-yl, 2H-5, 6-di-hydro-1, 2-thiazin-4-yl, 2H-5, 6-dihydro-l, 2-thiazin-5-yl, 2H-5, 6-dihydro-l, 2-thiazin-6- yl, 4H-5, 6-dihydro-l, 2-oxazin-3-yl, 4H-5, 6-dihydro-l, 2-oxazin-4-yl, 4H-5, 6-dihydro-

1, 2-oxazin-5-yl, 4H-5, 6-Dihydro-l, 2-oxazin-6-yl, 4H-5,6-Di- hydro-1, 2-thiazin-3-yl, 4H-5, 6-Dihydro-l, 2-thiazin-4-yl, 4H-5,6-Dihydro-l,2-thiazin-5-yl, 4H-5, 6-Dihydro-l, 2-thia- zin-6-yl, 2H-3, 6-Dihydro-l, 2-oxazin-3-yl, 2H-3 , 6-Dihydro- l,2-oxazin-4-yl, 2H-3, 6-Dihydro-l, 2-oxazin-5-yl, 2H-3,6-Di- hydro-1, 2-oxazin-6-yl, 2H-3, 6-Dihydro-l, 2-thiazin-3-yl, 2H-3 , 6-Dihydro-l , 2-thiazin-4-yl, 2H-3 , 6-Dihydro-l , 2-thia- zin-5-yl, 2H-3, 6-Dihydro-l, 2-thiazin-6-yl, 2H-3 , 4-Dihydro- l,2-oxazin-3-yl, 2H-3 , 4-Dihydro-l, 2-oxazin-4-yl, 2H-3,4-Di- hydro-1, 2-oxazin-5-yl, 2H-3, 4-Dihydro-l, 2-oxazin-6-yl,1, 2-oxazin-5-yl, 4H-5, 6-dihydro-l, 2-oxazin-6-yl, 4H-5,6-dihydro-1, 2-thiazin-3-yl, 4H- 5, 6-dihydro-l, 2-thiazin-4-yl, 4H-5,6-dihydro-l, 2-thiazin-5-yl, 4H-5, 6-dihydro-l, 2-thiazine 6-yl, 2H-3, 6-dihydro-l, 2-oxazin-3-yl, 2H-3, 6-dihydro-l, 2-oxazin-4-yl, 2H-3, 6-dihydro-l, 2-oxazin-5-yl, 2H-3,6-dihydro-1, 2-oxazin-6-yl, 2H-3, 6-dihydro-l, 2-thiazin-3-yl, 2H-3, 6-dihydro-l, 2-thiazin-4-yl, 2H-3, 6-dihydro-l, 2-thiazin-5-yl, 2H-3, 6-dihydro-l, 2-thiazin-6- yl, 2H-3,4-dihydro-l, 2-oxazin-3-yl, 2H-3,4, 4-dihydro-l, 2-oxazin-4-yl, 2H-3,4-dihydro-1, 2-oxazin-5-yl, 2H-3, 4-dihydro-l, 2-oxazin-6-yl,

2H-3 , 4-Dihydro-l , 2-thiazin-3-yl, 2H-3 , 4-Dihydro-l , 2-thia- zin-4-yl, 2H-3, 4-Dihydro-l, 2-thiazin-5-yl, 2H-3 , 4-Dihydro- 1, 2-thiazin-6-yl, 2,3,4, 5-Tetrahydropyridazin-3-yl, 2,3,4, 5-Tetrahydropyridazin-4-yl, 2,3,4, 5-Tetrahydropyrida- zin-5-yl, 2 , 3 , 4, 5-Tetrahydropyridazin-6-yl, 3 , 4 , 5, 6-Tetrahy- dropyridazin-3-yl, 3,4,5, 6-Tetrahydropyridazin-4-yl, 1,2,5, 6-Tetrahydropyridazin-3-yl, 1,2,5, 6-Tetrahydropyrida- zin-4-yl, 1, 2, 5, 6-Tetrahydropyridazin-5-yl, 1, 2 , 5, 6-Tetrahy- dropyridazin-6-yl, 1,2,3,6-Tetrahydropyridazin-3-yl, 1,2, 3, 6-Tetrahydropyridazin-4-yl, 4H-5, 6-Dihydro-l, 3-oxa- zin-2-yl, 4H-5, 6-Dihydro-l, 3-oxazin-4-yl, 4H-5,6-Di- hydro-1, 3-oxazin-5-yl, 4H-5, 6-Dihydro-l, 3-oxazin-6-yl, 4H-5 , 6-Dihydro-l , 3-thiazin-2-yl, 4H-5 , 6-Dihydro-l , 3-thia- zin-4-yl, 4H-5, 6-Dihydro-l, 3-thiazin-5-yl, 4H-5, 6-Dihydro- l,3-thiazin-6-yl, 3, 4, 5-6-Tetrahydropyrimidin-2-yl,2H-3,4-dihydro-1,2-thiazin-3-yl, 2H-3,4,4-dihydro-1,2-thiazin-4-yl, 2H-3,4-dihydro-1,2 thiazin-5-yl, 2H-3,4,4-dihydro-1,2-thiazin-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-l, 3-oxazin-2-yl, 4H-5, 6-dihydro-l, 3-oxazin-4-yl, 4H-5,6-dihydro-1, 3-oxazin-5-yl, 4H-5, 6-dihydro-l, 3-oxazin-6-yl, 4H-5, 6-dihydro-l, 3-thiazin-2-yl, 4H-5, 6- Dihydro-l, 3-thiazin-4-yl, 4H-5, 6-dihydro-l, 3-thiazin-5-yl, 4H-5, 6-dihydro-l, 3-thiazin-6-yl, 3, 4, 5-6-tetrahydropyrimidin-2-yl,

3,4,5, 6-Tetrahydropyrimidin-4-yl , 3,4,5, 6-Tetrahydro- pyrimidin-5-yl, 3, 4, 5, 6-Tetrahydropyrimidin-6-yl, 1,2,3,4-Te- trahydropyrazin-2-yl, 1,2,3, 4-Tetrahydropyrazin-5-yl, 1,2,3, 4-Tetrahydropyrimidin-2-yl , 1,2,3, 4-Tetrahydropyrimi- din-4-yl, 1, 2, 3, 4-Tetrahydropyrimidin-5-yl, 1, 2 , 3, 4-Tetra- hydropyrimidin-6-yl, 2, 3-Dihydro-l, 4-thiazin-2-yl, 2,3-Di- hydro-l,4-thiazin-3-yl, 2, 3-Dihydro-l, 4-thiazin-5-yl, 2,3-Di- hydro-l,4-thiazin-6-yl, 2H-1, 2-Oxazin-3-yl, 2H-1, 2-Oxazin-4- yl, 2H-l,2-Oxazin-5-yl, 2H-1, 2-Oxazin-6-yl, 2H-1, 2-Thiazin-3- yl, 2H-l,2-Thiazin-4-yl, 2H-1, 2-Thiazin-5-yl, 2H-1,2-Thiazin- 6-yl, 4H-l,2-Oxazin-3-yl, 4H-1, 2-Oxazin-4-yl, 4H-1, 2-Oxazin- 5-yl, 4H-l,2-Oxazin-6-yl, 4H-1, 2-Thiazin-3-yl, 4H-1,2-Thia- zin-4-yl, 4H-1, 2-Thiazin-5-yl, 4H-1, 2-Thiazin-6-yl, 6H-l,2-Oxazin-3-yl, 6H-1, 2-Oxazin-4-yl, 6H-1, 2-Oxazin-5-yl, 6H-l,2-Oxazin-6-yl, 6H-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-yl, 2H-l,3-Thiazin-2-yl, 2H-1, 3-Thiazin-4-yl, 2H-1, 3-Thiazin-5- yl, 2H-l,3-Thiazin-6-yl, 4K-1, 3-Oxazin-2-yl, 4H-1, 3-Oxazin- 4-yl, 4H-l,3-Oxazin-5-yl, 4H-1, 3-Oxazin-6-yl, 4H-1, 3-Thiazin- 2-yl, 4H-l,3-Thiazin-4-yl, 4H-1, 3-Thiazin-5-yl, 4H-1,3-Thia- zin-6-yl, 6H-1, 3-Oxazin-2-yl, 6H-1, 3-Oxazin-4-yl, 6H-l,3-Oxa- zin-5-yl, 6H-1, 3-Oxazin-6-yl, 6H-1, 3-Thiazin-2-yl, 6H-l,3-Oxazin-4-yl, 6H-1, 3-Oxazin-5-yl, 6H-1, 3-Thiazin-6-yl, 2H-l,4-Oxazin-2-yl, 2H-1, 4-Oxazin-3-yl, 2H-1, 4-Oxazin-5-yl, 2H-l,4-Oxazin-6-yl, 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-Di- hydropyridazin-5-yl, 1, 4-Dihydropyridazin-6-yl, 1,4-Dihydro- pyrazin-2-yl, 1, 2-Dihydropyrazin-2-yl, 1, 2-Dihydropyrazin- 3-yl, l,2-Dihydropyrazin-5-yl, 1, 2-Dihydropyrazin-6-yl,3,4,5, 6-tetrahydropyrimidin-4-yl, 3,4,5, 6-tetrahydropyrimidin-5-yl, 3, 4, 5, 6-tetrahydropyrimidin-6-yl, 1,2,3, 4-tetrahydropyrazin-2-yl, 1,2,3, 4-tetrahydropyrazin-5-yl, 1,2,3, 4-tetrahydropyrimidin-2-yl, 1,2,3, 4-tetrahydropyrimididine 4-yl, 1, 2, 3, 4-tetrahydropyrimidin-5-yl, 1, 2, 3, 4-tetrahydropyrimidin-6-yl, 2, 3-dihydro-l, 4-thiazin-2-yl, 2,3-di-hydro-l, 4-thiazin-3-yl, 2,3-dihydro-l, 4-thiazin-5-yl, 2,3-di-hydro-l, 4-thiazin-6- yl, 2H-1, 2-oxazin-3-yl, 2H-1, 2-oxazin-4- yl, 2H-l, 2-oxazin-5-yl, 2H-1, 2-oxazin-6-yl, 2H-1, 2-thiazin-3-yl, 2H-1, 2-thiazin-4-yl, 2H-1, 2-thiazin-5-yl, 2H-1,2-thiazine-6-yl, 4H- l, 2-oxazin-3-yl, 4H-1, 2-oxazin-4-yl, 4H-1, 2-oxazin-5-yl, 4H-l, 2-oxazin-6-yl, 4H-1, 2-thiazin-3-yl, 4H-1,2-thia zin-4-yl, 4H-1, 2-thiazin-5-yl, 4H-1, 2-thiazin-6-yl, 6H-1, 2-oxazin-3-yl, 6H-1, 2-oxazin- 4-yl, 6H-1, 2-oxazin-5-yl, 6H-l, 2-oxazin-6-yl, 6H-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-yl, 2H-1, 3-thiazin-2-yl, 2H-1, 3-thiazin-4-yl, 2H- 1, 3-thiazin-5- yl, 2H-l, 3-thiazin-6-yl, 4K-1, 3-oxazin-2-yl, 4H-1, 3-oxazin-4-yl, 4H-l, 3-oxazin-5-yl, 4H-1, 3-oxazin-6-yl, 4H-1, 3-thiazin- 2-yl, 4H-l, 3-thiazin-4-yl, 4H-1, 3- Thiazin-5-yl, 4H-1,3-thiazin-6-yl, 6H-1, 3-oxazin-2-yl, 6H-1, 3-oxazin-4-yl, 6H-l, 3- Oxazine-5-yl, 6H-1,3-oxazin-6-yl, 6H-1,3-thiazin-2-yl, 6H-1,3-oxazin-4-yl, 6H-1,3- Oxazin-5-yl, 6H-1, 3-thiazin-6-yl, 2H-l, 4-oxazin-2-yl, 2H-1, 4-oxazin-3-yl, 2H-1, 4-oxazin- 5-yl, 2H-l, 4-oxazin-6-yl, 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-dihyd ropyridazin-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, 1, 4-Dihydropyrimidin-4-yl, 1,4-Di- hydropyrimidin-5-yl, 1, 4-Dihydropyrimidin-6-yl, 3,4-Dihydro- pyrimidin-2-yl, 3, 4-Dihydropyrimidin-4-yl, 3, 4-Dihydropyrimi- din-5-yl oder 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-Triazin-3-yl, 1,2, 4-Triazin-5-yl, 1, 2, 4-Triazin-6-yl, 1, 2, 4, δ-Tetra- zin-S-yl;1,4-dihydropyrimidin-2-yl, 1,4-dihydropyrimidin-4-yl, 1,4-dihydropyrimidin-5-yl, 1,4-dihydropyrimidin-6-yl, 3,4-dihydropyrimidin- 2-yl, 3,4-dihydropyrimidin-4-yl, 3,4-dihydropyrimidin-5-yl or 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-triazin-3-yl, 1,2, 4-triazin-5-yl, 1, 2, 4-triazin-6-yl, 1, 2, 4, δ-tetrazin-S-yl;

wobei ggf. 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 ;

und wobei mit einem ankondensierten Phenylring oder mit einem C3-C6-Carbocyclus oder mit einem weiteren 5- bis 6-gliedrigen Heterocyclus ein bicyclisches Ringsystem ausgebildet werden kann.and a bicyclic ring system can be formed with a fused-on phenyl ring or with a C 3 -C 6 carbocycle or with a further 5- to 6-membered heterocycle.

N-gebundenes Heterocyclyl: ein gesättigter, partiell gesättigter oder ungesättigter 5- oder 6-gliedriger N-gebundener heterocyclischer Ring, der mindestens einen Stickstoff und gegebenenfalls ein bis drei gleiche oder verschiedene Hetero- atome, ausgewählt aus folgender Gruppe: Sauerstoff, Schwefel oder Stickstoff enthält, also z.B.N-linked heterocyclyl: a saturated, partially saturated or unsaturated 5- or 6-membered N-linked heterocyclic ring, the at least one nitrogen and optionally one to three identical or different hetero atoms, selected from the following group: oxygen, sulfur or nitrogen contains, e.g.

N-gebundene 5-gliedrige Ringe wie: Tetrahydropyrrol-1-yl, 2, 3-Dihydro-lH-pyrrol-l-yl, 2,5-Di- hydro-lH-pyrrol-1-yl, Pyrrol-1-yl, Tetrahydropyrazol-1-yl, Tetrahydroisoxazol-2-yl, Tetrahydroisothiazol-2-yl, Tetra- hydroimidazol-1-yl, Tetrahydrooxazol-3-yl, Tetrahydrothia- zol-3-yl, 4, 5-Dihydro-lH-pyrazol-l-yl, 2, 5-Dihydro-lH-pyra- zol-l-yl, 2,3-Dihydro-lH-pyrazol-l-yl, 2, 5-Dihydroisoxazol- 2-yl, 2 , 3-Dihydroisoxazol-2-yl, 2 , 5-Dihydroisothiazol-2-yl, 2 , 3-Dihydroisoxazol-2-yl , 4 , 5-Dihydro-lH-imidazol-l-yl , 2, 5-Dihydro-lH-imidazol-l-yl, 2, 3-Dihydro-lH-imidazol-l-yl, 2, 3-Dihydrooxazol-3-yl, 2 , 3-Dihydrothiazol-3-yl, Pyrazol-1- yl, Imidazol-1-yl, 1, 2 , -Δ4-0xadiazolin-2-yl, 1, 2, 4-Δ2-Oxa- diazolin-4-yl, 1, 2, 4-Δ3-Oxadiazolin-2-yl, 1, 3, 4-Δ2-Oxadiazo- lin-4-yl, 1, 2 , 4-Δ5-Thiadiazolin-2-yl, 1, 2, 4-Δ3-Thiadiazo- lin-2-yl, 1, 2, 4-Δ2-Thiadiazolin-4-yl, 1, 3, 4-Δ2-Thiadiazo- lin-4-yl, 1, 2, 3-Δ2-Triazolin-l-yl, 1, 2 , 4-Δ2-Triazolin-l-yl, l,2,4-Δ2-Triazolin-4-yl, 1 , 2 , -Δ3-Triazolin-l-yl, 1,2,4-Δ1- Triazolin-4-yl, 1, 2, 3-Triazol-l-yl, 1, 2, -Triazol-l-yl, Tetrazol-1-yl;N-linked 5-membered rings such as: Tetrahydropyrrol-1-yl, 2,3-dihydro-lH-pyrrol-l-yl, 2,5-di-hydro-lH-pyrrol-1-yl, pyrrol-1-yl, tetrahydropyrazol-1-yl, tetrahydroisoxazole 2-yl, tetrahydroisothiazol-2-yl, tetrahydroimidazol-1-yl, tetrahydrooxazol-3-yl, tetrahydrothiazol-3-yl, 4,5-dihydro-lH-pyrazol-l-yl, 2,5- Dihydro-lH-pyrazol-l-yl, 2,3-dihydro-lH-pyrazol-l-yl, 2,5-dihydroisoxazol-2-yl, 2,3-dihydroisoxazol-2-yl, 2,5- Dihydroisothiazol-2-yl, 2,3-dihydroisoxazol-2-yl, 4,5-dihydro-lH-imidazol-l-yl, 2,5-dihydro-lH-imidazol-l-yl, 2,3-dihydro lH-imidazol-l-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrothiazol-3-yl, pyrazol-1-yl, imidazol-1-yl, 1,2, -Δ 4 -xadiazolin- 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 -thiadiazo-lin-2-yl, 1, 2, 4-Δ 2 -thiadiazolin-4-yl, 1, 3, 4-Δ 2 -thiadiazo-lin-4-yl, 1, 2, 3-Δ 2 -triazolin-l-yl, 1, 2, 4-Δ 2 -triazolin-l-yl, 1, 2 , 4-Δ 2 -triazolin-4-yl, 1, 2, -Δ 3- triazolin-l-yl, 1,2,4-Δ 1 - triazolin-4-yl, 1, 2, 3-triazol-l-yl, 1, 2, -triazol-l-yl, tetrazol-1- yl;

sowie N-gebundene 6-gliedrige Ringe wie:as well as N-linked 6-membered rings such as:

Piperidin-1-yl, 1, 2, 3 , 4-Tetrahydropyridin-l-yl, 1,2,5,6-Te- trahydropyridin-1-yl, 1, 4-Dihydropyridin-l-yl, 1,2-Dihydro- pyridin-1-yl, Hexahydropyrimidin-1-yl, Hexahydropyrazin-1-yl, Hexahydropyridazin-1-yl, Tetrahydro-1, 3-oxazin-3-yl, Tetra- hydro-1, 3-thiazin-3-yl, Tetrahydro-1, 4-thiazin-4-yl, Tetra- hydro-1, 4-oxazin-4-yl, Tetrahydro-1, 2-oxazin-2-yl, 2H-5,6-Di- hydro-1, 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-3,4-Dihydro-oxazin-2-yl, 2H-3, 4-Dihydro-l, 2-thiazin- 2-yl, 2, 3, 4, 5-Tetrahydropyridazin-2-yl, 1, 2 , 5, 6-Tetrahydropy- ridazin-l-yl, 1,2, 5, 6-Tetrahydropyridazin-2-yl, 1,2,3,6-Te- trahydropyridazin-1-yl , 3,4,5, 6-Tetrahydropyrimidin-3-yl, 1,2,3, 4-Tetrahydropyrazin-l-yl , 1,2,3, 4-Tetrahydro- pyrimidin-1-yl, 1,2, 3 , 4-Tetrahydropyrimidin-3-yl, 2,3-Dih- dro-l,4-thiazin-4-yl, 2H-1, 2-Oxazin-2-yl, 2H-1, 2-Thiazin- 2-yl, 4H-l,4-Oxazin-4-yl, 4H-1, 4-Thiazin-4-yl, 1, 4-Dihydropy- ridazin-l-yl, 1,4-Dihydropyrazin-l-yl, 1, 2-Dihydropyra- zin-l-yl, 1, 4-Dihydropyrimidin-l-yl oder 3, 4-Dihydropyrimi- din-3-yl, sowie N-gebundene cyclische Imide wie:Piperidin-1-yl, 1, 2, 3, 4-tetrahydropyridin-l-yl, 1,2,5,6-tetrahydropyridin-1-yl, 1, 4-dihydropyridin-l-yl, 1,2- Dihydropyridin-1-yl, hexahydropyrimidin-1-yl, hexahydropyrazin-1-yl, hexahydropyridazin-1-yl, tetrahydro-1, 3-oxazin-3-yl, tetrahydro-1, 3-thiazin-3- yl, tetrahydro-1, 4-thiazin-4-yl, tetrahydro-1, 4-oxazin-4-yl, tetrahydro-1, 2-oxazin-2-yl, 2H-5,6-dihydro 1, 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-thiazine-2-yl, 2H-3,4-dihydro-oxazin-2-yl, 2H-3,4, 4-dihydro-l, 2-thiazine-2-yl, 2, 3, 4, 5-tetrahydropyridazin-2-yl, 1, 2, 5, 6-tetrahydropyridazin-l-yl, 1,2, 5, 6-tetrahydropyridazin-2-yl, 1,2,3,6-te- trahydropyridazin-1-yl, 3,4,5, 6-tetrahydropyrimidin-3-yl, 1,2,3, 4-tetrahydropyrazin-l-yl, 1,2,3, 4-tetrahydropyrimidin-1-yl, 1,2,3,4-tetrahydropyrimidin-3-yl, 2,3-dihydro-l, 4-thiazin-4-yl, 2H-1,2,2-oxazin-2-yl, 2H-1,2 Thiazin-2-yl, 4H-l, 4-oxazin-4-yl, 4H-1, 4-thiazin-4-yl, 1, 4-dihydropyrid azin-l-yl, 1,4-dihydropyrazine-l-yl, 1,2-dihydropyrazine-l-yl, 1,4-dihydropyrimidin-l-yl or 3,4-dihydropyrimidine-3-yl, as well as N-linked cyclic imides such as:

Phthalsäureimid, Tetrahydrophthalsäureimid, Succinimid, Ma- leinimid oder Glutarimid;Phthalimide, tetrahydrophthalimide, succinimide, maleimide or glutarimide;

Alle Phenylringe bzw. Heterocyclylreste sowie alle Phenylkompo- nenten in Phenyl-alkyl, Phenylcarbonyl-alkyl, Phenylcarbonyl,All phenyl rings or heterocyclyl residues and all phenyl components in phenyl-alkyl, phenylcarbonyl-alkyl, phenylcarbonyl,

Phenylalkylcarbonyl, Phenylalkenylcarbonyl, Phenoxycarbonyl, Phe- nyloxythiocarbonyl, Phenylaminocarbonyl, N-Alkyl-N-phenylamino- carbonyl, Phenylsulfonyl und Phenoxysulfonyl bzw. alle Heterocyc- lylkomponenten in Heterocyclyl-alkyl, Heterocyclylcarbonyl-alkyl, Heterocyclylcarbonyl , Heterocyclylalkylcarbonyl , Heterocyclylal - kenylcarbonyl , Heterocyclyloxycarbonyl , Heterocyclyloxythiocarbo - nyl, Heterocyclylaminocarbonyl, N-Alkyl-N-heterocyclylaminocarbonyl, Heterocyclylsulfonyl und Heterocyclyloxysulfonyl sind, soweit nicht anders angegeben, vorzugsweise unsubstituiert oder tragen ein bis drei Haloger-atome und/oder eine Nitrogruppe, einen Cyanorest und/oder einen oder zwei Methyl-, Trifluormethyl-, Methoxy- oder Trifluormethoxysubstituenten.Phenylalkylcarbonyl, phenylalkenylcarbonyl, phenoxycarbonyl, phenyloxythiocarbonyl, phenylaminocarbonyl, N-alkyl-N-phenylamino carbonyl, phenylsulfonyl or phenoxysulfonyl and all heterocycles in lylkomponenten heterocyclyl alkyl, heterocyclylcarbonyl-alkyl, heterocyclylcarbonyl, heterocyclylalkylcarbonyl, Heterocyclylal - kenylcarbonyl, heterocyclyloxycarbonyl, Heterocyclyloxythiocarbo - nyl, N-alkyl-N-heterocyclylaminocarbonyl, and heterocyclylsulfonyl Heterocyclyloxysulfonyl Heterocyclylaminocarbonyl are, as far as not stated otherwise, preferably unsubstituted or carry one to three halogen atoms and / or a nitro group, a cyano radical and / or one or two methyl, trifluoromethyl, methoxy or trifluoromethoxy substituents.

Die erfindungsgemäßen Verbindungen der Formel I mit R9 = Ha werden als Verbindungen der Formel la sowie Verbindungen der Formel I mit R9 = Ilb als Ib bezeichnet.The compounds of the formula I according to the invention with R 9 = Ha are referred to as compounds of the formula Ia and compounds of the formula I with R 9 = Ilb as Ib.

Bevorzugt sind tricyclische Cyclohexandionderivate der Formel IIITricyclic cyclohexanedione derivatives of the formula III are preferred

Figure imgf000030_0001
Figure imgf000030_0001

in der die Substituenten die oben angegebenen Bedeutungen haben.in which the substituents have the meanings given above.

Bevorzugt sind auch tricyclische Cyclohexandionderivate der Formel IVTricyclic cyclohexanedione derivatives of the formula IV are also preferred

Figure imgf000030_0002
Figure imgf000030_0002

in der die Substituenten die oben angegebenen Bedeutungen haben.in which the substituents have the meanings given above.

In Hinblick auf die Verwendung der erfindungsgemäßen Verbindungen der Formeln I, III bzw. IV als Herbizide haben die Variablen vorzugsweise folgende Bedeutungen, und zwar jeweils für sich al- lein oder in Kombination: Ri Wasserstoff, Cχ-C6 -Alkyl, Cχ-C6-Haloalkyl,With regard to the use of the compounds of the formulas I, III or IV according to the invention as herbicides, the variables preferably have the following meanings, in each case individually or in combination: Ri is hydrogen, Cχ-C 6 -alkyl, Cχ-C 6 -haloalkyl,

Cχ-C6-Alkoxy, Cχ-C6 -Alkylthio, Cχ-C6 -Alkylsulfonyl, Halogen, Cyano oder Nitro;Cχ-C 6 alkoxy, Cχ-C 6 alkylthio, Cχ-C 6 alkylsulfonyl, halogen, cyano or nitro;

R2 Wasserstoff, Cχ-C6 -Alkyl, Cχ-C6-Alkoxy, Cχ-C6-Halo- alkyl, Cχ-Cδ -Haloalkoxy, gegebenenfalls mit Cχ-C3 -Alkyl, Halogen, Cyano, Nitro oder Cχ-C3-Alkyl- sulfonyl substituiertes Phenyl oder gegebenenfalls mit Cχ-C3 -Alkyl, Halogen, Cyano oder Nitro substi- tuiertes Phenylsulfonyl;R 2 is hydrogen, Cχ-C 6 alkyl, Cχ-C 6 alkoxy, Cχ-C 6 haloalkyl, Cχ-C δ -haloalkoxy, optionally with C gegebenenfalls-C 3 alkyl, halogen, cyano, nitro or Cχ -C 3 alkyl sulfonyl substituted phenyl or phenyl sulfonyl optionally substituted with Cχ-C 3 alkyl, halogen, cyano or nitro;

R3, R4 Wasserstoff, Cχ-C6 -Alkyl, Cχ-C6 -Alkoxy, Cχ-C6-Alkylthio, Cχ-C6-Alkylsulfonyl, C2-C6-Alkoxyalkyl, Cχ-C6 -Alkoxycarbonyl, Cχ-Cδ-Alkylcarbonyl, Halogen, gegebenenfalls mit Cχ-C3 -Alkyl, Halogen, Cyano oderR 3 , R 4 are hydrogen, Cχ-C 6 -alkyl, Cχ-C 6 -alkoxy, Cχ-C 6 -alkylthio, Cχ-C 6 -alkylsulfonyl, C 2 -C 6 -alkoxyalkyl, Cχ-C 6 -alkoxycarbonyl, Cχ-C δ alkylcarbonyl, halogen, optionally with Cχ-C 3 alkyl, halogen, cyano or

Nitro substituiertes Phenyl;Nitro substituted phenyl;

R5 Wasserstoff;R 5 is hydrogen;

R6 Wasserstoff, Cχ-C3 -Alkyl oder Halogen,-R 6 is hydrogen, Cχ-C 3 alkyl or halogen,

n 1 oder 2.n 1 or 2.

Ro Hydroxy, Mercapto, Halogen, OR"7, SR1 , SORi8, S02Ri8, OS02Ri8, OP(0)Ri9R20, OP(S)Ri9R20< NR2R22, ORi8Ri8 oderRo Hydroxy, Mercapto, Halogen, OR "7 , SR 1 , SORi 8 , S0 2 Ri 8 , OS0 2 R i8 , OP (0) R i9 R 20 , OP (S) R i9 R 20 <NR 2 R 22 , OR i8 R i8 or

N-gebundenes Heterocyclyl, das partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, Cχ.C4-Alkyl, Cχ-C4-Halogenalkyl, Cχ-C4-Alkoxy oder Cχ-C4 -Halogenalkoxy; bevorzugt Hydroxy, Mercapto, Halogen, ORi"7, SRi7, S02Ri8, OS02Ri8, NR2iR22, ONR18Ri8 oder N-gebundenes Heterocyclyl, das partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, Cχ-C4-Alkyl,N-linked heterocyclyl, which can be partially or completely halogenated and / or can carry one to three of the following radicals: nitro, cyano, Cχ.C 4 alkyl, Cχ-C 4 haloalkyl, Cχ-C 4 alkoxy or Cχ -C 4 haloalkoxy; preferably hydroxy, mercapto, halogen, OR i "7 , SR i7 , S0 2 R i8 , OS0 2 R i8 , NR 2i R 22 , ONR 18 R i8 or N-linked heterocyclyl, which can be partially or completely halogenated and / or can carry one to three of the following radicals: nitro, cyano, Cχ-C 4 alkyl,

Cχ-C4-Halogenalkyl, Cχ-C4-Alkoxy oder Cχ-C4-Halogenalkoxy;Cχ-C 4 haloalkyl, Cχ-C 4 alkoxy or Cχ-C 4 haloalkoxy;

Ri, Ri5 Wasserstoff oder Cχ-C4 -Alkyl, wie Methyl, Ethyl oder Propyl; bevorzugt Wasserstoff oder Methyl;Ri, Ri 5 is hydrogen or Cχ-C 4 alkyl, such as methyl, ethyl or propyl; preferably hydrogen or methyl;

Ri2, R4, Ri6 Wasserstoff oder Cχ-C4 -Alkyl, wie Methyl, Ethyl oder Propyl ; bevorzugt Wasserstoff oder Methyl; R3 Wasserstoff, Hydroxy, Cχ-C6 -Alkyl, Di- (Cχ-C6-alk- oxy) -methyl, (Cχ-Ce -Alkoxy) - (Cχ-C6 -alkylthio) -methyl, Di- (Cχ-C6-alkylthio)methyl, Cχ-C6 -Alkylthio, Cx -C6 -Halogenalky1thio, C -C6-Alkylsulfinyl, Cχ-C6"Halogenalkylsulfinyl, Cχ-Cδ -Alkylsulfonyl oderR i2 , R 4 , R i6 hydrogen or Cχ-C 4 alkyl, such as methyl, ethyl or propyl; preferably hydrogen or methyl; R 3 is hydrogen, hydroxy, Cχ-C6-alkyl, di- (Cχ-C 6 -alk-oxy) -methyl, (Cχ-Ce -alkoxy) - (Cχ-C 6 -alkylthio) -methyl, di- (Cχ -C 6 -alkylthio) methyl, Cχ-C 6 alkylthio, Cx-C6 -Halogenalky1thio, C-C6 alkylsulfinyl, Cχ-C 6 "haloalkylsulfinyl, alkylsulfonyl or Cχ-C δ

Cχ-C6-Halogenalkylsulfonyl;Cχ-C 6 haloalkylsulfonyl;

l,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 letztgenannten1,3-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, the latter six

Reste durch einen bis drei Cχ-C4-Alkylreste substituiert sein können;Radicals can be substituted by one to three Cχ-C 4 alkyl radicals;

bevorzugt Wasserstoff, Hydroxy oder Cχ-C4 -Alkyl, wie Methyl, Ethyl oder Propyl;preferably hydrogen, hydroxy or Cχ-C 4 alkyl, such as methyl, ethyl or propyl;

oderor

Ri2 und R13 oder R12 und Ri6 bilden gemeinsam eine π-Bindung oder eine C3 -C5 -Alkylkette, die eien bis drei Reste aus folgenderR i2 and R 13 or R 12 and R i6 together form a π bond or a C 3 -C 5 alkyl chain which have up to three residues from the following

Gruppe tragen kan: Halogen, Cyano, Cχ -C4 -Alkyl , Cχ -C4 -Halogenalkyl oder Cχ -C4 -Alkoxycarbonyl , aus ;Group can carry: halogen, cyano, Cχ -C 4 alkyl, Cχ -C 4 haloalkyl or Cχ -C 4 alkoxycarbonyl, from;

oderor

Ri2 und R16 bilden gemeinsam eine Cχ-C4-Alkylkette, die eine bis drei Reste aus folgender Gruppe tragen kann: Halogen, Cyano, Cχ-C4-Alkyl, Cχ-C4-Halogenalkyl oder Cχ-C4 -Alkoxycarbonyl, aus;Ri 2 and R 16 together form a Cχ-C 4 alkyl chain which can carry one to three radicals from the following group: halogen, cyano, Cχ-C 4 alkyl, Cχ-C 4 haloalkyl or Cχ-C 4 alkoxycarbonyl , out;

oderor

R3 und Rl4 bilden gemeinsam eine -0- (CH2)p-0- , -0-(CH2)p-S- oder -S- (CH2)P-S-Kette, die durch einen bis drei Reste aus folgender Gruppe substituiert sein kann: Halogen, Cyano, Cχ-C4-Alkyl, Cχ-C4-Halogenalkyl oder Cχ- ι -Alkoxycarbonyl; bevorzugt bilden R13 und Ri4 gemeinsam eine -O- (CH )p-0- , -0-(CH2)p-S- oder -S- (CH2)p-S-Kette, die durch einen bis drei der Reste aus folgender Gruppen substituiert sein kann: Cx-C4-Halogen- alkyl oder Cχ-C4 -Alkoxycarbonyl;R 3 and Rl 4 together form a -0- (CH 2 ) p -0-, -0- (CH 2 ) p -S- or -S- (CH 2 ) P -S chain, which by one to three Residues from the following group can be substituted: halogen, cyano, Cχ-C 4 alkyl, Cχ-C 4 haloalkyl or Cχ- ι alkoxycarbonyl; preferably R 13 and R i4 together form a -O- (CH) p -0-, -0- (CH 2 ) p -S- or -S- (CH 2 ) p -S chain, which is represented by one to three the radicals from the following groups can be substituted: Cx-C 4 haloalkyl or Cχ-C 4 alkoxycarbonyl;

oderor

Ri3 und Ri4 bilden gemeinsam mit dem Kohlenstoff, an dem sie gebunden sind, eine Carbonylgruppe aus; Cχ-Cε -Alkyl, C3-C6-Alkenyl, C3-C6-Halogenalkenyl,R i3 and R i4 together with the carbon to which they are attached form a carbonyl group; Cχ-Cε alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl,

C3-C6 -Alkinyl, Cχ-Ce -Alkylcarbonyl, C2-C6-Alkenylcarbonyl , C3 -C5 -Cycloalkylcarbony1, Cx -C6 -Alkoxycarbonyl , C3-C6 -Alkenyloxycarbonyl, C3 -C6 -Alkinyloxycarbonyl, Cχ-C6-Alkylthiocarbonyl, Cχ-C6 -Alkylaminocarbonyl,C 3 -C 6 alkynyl, Cχ-Ce alkylcarbonyl, C 2 -C 6 alkenylcarbonyl, C 3 -C 5 cycloalkylcarbonyl1, Cx -C 6 alkoxycarbonyl, C 3 -C 6 alkenyloxycarbonyl, C 3 -C 6 -Alkynyloxycarbonyl, Cχ-C 6 -alkylthiocarbonyl, Cχ-C 6 -alkylaminocarbonyl,

C3 -C6 -Alkenylaminocarbonyl , C3- C -Alkinylaminocarbonyl , N,N-Di (Cχ-C6 -alkyl) aminocarbonyl, N- (C3-C6 -Alkenyl) -N- (Cχ-C6-alkyl) -aminocarbonyl, N- (C3-C6 -Alkinyl) -N- (Cχ-C6-alkyl) -aminocarbonyl, N- (Cχ-C6-Alk- oxy) -N- (Cχ-C6-alkyl) -aminocarbonyl, N- (C3-C6-Alkenyl) -N- (Cχ-C6 -alkoxy) -aminocarbonyl, N- (C3-Cδ-Alkin- yl) -N- (Cχ-C6-alkoxy) -aminocarbonyl, Di- (Cχ-C6-alk- yl) -aminothiocarbonyl, Cx -C6-Alkoxyimino-Cχ-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, Cχ-C4-Alkoxy, Cχ-C4 -Alkylthio, Di- (Cχ-C4 -alkyl) - amino, Cχ-C4 -Alkylcarbonyl, Cχ-C4 -Alkoxycarbonyl, Hydroxy- carbonyl, Cχ-C4 -Alkylaminocarbonyl, Di- (Cχ-C4 -Alkyl) amino- carbonyl, Cχ-C4-Aikylcarbonyloxy oder C3 -C6-Cycloalkyl,-C 3 -C 6 alkenylaminocarbonyl, C 3 - C alkynylaminocarbonyl, N, N-di (Cχ-C 6 -alkyl) aminocarbonyl, N- (C 3 -C 6 -alkenyl) -N- (Cχ-C 6 - alkyl) -aminocarbonyl, N- (C 3 -C 6 -alkynyl) -N- (Cχ-C 6 -alkyl) -aminocarbonyl, N- (Cχ-C 6 -alkoxy) -N- (Cχ-C 6 -alkyl) -aminocarbonyl, N- (C 3 -C 6 -alkenyl) -N- (Cχ-C 6 -alkoxy) -aminocarbonyl, N- (C 3 -C δ -alkynyl-yl) -N- (Cχ- C 6 -alkoxy) -aminocarbonyl, di- (Cχ-C 6 -alk- yl) -aminothiocarbonyl, Cx -C 6 -alkoxyimino-Cχ-C 6 -alkyl, where the alkyl, cycloalkyl or alkoxy radicals mentioned partially or completely can be halogenated and / or can carry one to three of the following groups: cyano, Cχ-C 4 -alkoxy, Cχ-C 4 -alkylthio, di- (Cχ-C 4 -alkyl) - amino, Cχ-C 4 -alkylcarbonyl , Cχ-C 4 -alkoxycarbonyl, hydroxycarbonyl, Cχ-C 4 -alkylaminocarbonyl, di- (Cχ-C 4 -alkyl) amino-carbonyl, Cχ-C 4 -alkylcarbonyloxy or C 3 -C 6 -cycloalkyl, -

Phenyl, Phenyl -Cχ-C6 -alkyl, Phenylcarbonyl-Cχ-C6-alkyl, Phenylcarbonyl, Phenoxycarbonyl, Phenoxythiocarbonyl, Phenyl -C2-C6-alkenylcarbonyl, Heterocyclyl, Heterocy- clyl-Cχ-C6-alkyl, Heterocyclylcarbonyl -Cχ-C6- alkyl, Heterocyclylcarbonyl, Heterocyclyloxycarbonyl, Heterocyclyloxythiocarbonyl oder Heterocyclyl -Cχ-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, Cχ-C4 -Alkyl, Cχ-C4-Halogenalkyl, Cχ-C4-Alkoxy oder Cχ-C4 -Halogenalkoxy;Phenyl, phenyl -Cχ-C 6 -alkyl, phenylcarbonyl-Cχ-C 6 -alkyl, phenylcarbonyl, phenoxycarbonyl, phenoxythiocarbonyl, phenyl -C 2 -C 6 -alkenylcarbonyl, heterocyclyl, heterocyclyl-Cχ-C 6 -alkyl, heterocyclylcarbonyl -Cχ-C 6 - alkyl, heterocyclylcarbonyl, heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl or heterocyclyl -Cχ-C 6 -alkenylcarbonyl, where the phenyl or the heterocyclyl radical of the latter 14 substituents can be partially or completely halogenated and / or one to three of the following Residues can carry: nitro, cyano, Cχ-C 4 alkyl, Cχ-C 4 haloalkyl, Cχ-C 4 alkoxy or Cχ-C 4 haloalkoxy;

bevorzugt Cχ-C6 -Alkyl, C3-C6 -Alkenyl, C3-C6 -Alkinyl, Cχ-C6 -Alkylcarbonyl, Cχ-C6 -Alkoxycarbonyl, Cχ-C6-Alkylaminocarbonyl oder N,N-Di (Cχ-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, Cχ-C4-Alkoxy, Cχ-C4 -Alkylthio oder Cχ-C4-Alkoxycarbonyl;preferably Cχ-C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, Cχ-C 6 alkylcarbonyl, Cχ-C 6 alkoxycarbonyl, Cχ-C 6 alkylaminocarbonyl or N, N-di (Cχ-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, Cχ-C 4 alkoxy, Cχ-C 4 alkylthio or Cχ-C 4 alkoxycarbonyl;

Phenyl, Phenyl -Cχ-C6-alkyl, Phenylcarbonyl-Cχ-C6-alkyl, Phenylcarbonyl, Phenoxycarbonyl, Heterocyclyl-, Heterocyclyl -Cχ-C6-alkyl, Heterocyclylcarbonyl -Cχ-Cδ- alkyl, Hete- rocyclylcarbonyl oder Heterocyclyloxycarbonyl, 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, Cχ-C4 -Alkyl, Cχ-C4-Halogenalkyl, Cχ-C4 -Alkoxy oder Cχ-C4 -Halogenalkoxy,-Phenyl, phenyl -Cχ-C 6 -alkyl, phenylcarbonyl-Cχ-C 6 -alkyl, phenylcarbonyl, phenoxycarbonyl, heterocyclyl-, heterocyclyl -Cχ-C 6 -alkyl, heterocyclylcarbonyl -Cχ-C δ - alkyl, heterocyclylcarbonyl or heterocyclyloxycarbonyl , wherein the phenyl or heterocyclyl radical of the 10 last-mentioned substituents are partially or completely halogenated can or / or can carry one to three of the following radicals: nitro, cyano, Cχ-C 4 -alkyl, Cχ-C 4 -haloalkyl, Cχ-C 4 -alkoxy or Cχ-C 4 -haloalkoxy, -

R18 Cχ-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, Cχ-C4 -Alkoxy, Cχ-C4-Alkylthio, Cχ-C -Alkylcarbonyl oder Cχ-C4 -Alkoxycarbonyl;R 18 is Cχ-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, Cχ-C 4 alkoxy, Cχ-C 4 alkylthio, Cχ-C alkylcarbonyl or Cχ-C 4 alkoxycarbonyl;

Phenyl, Phenyl -Cχ-C4-alkyl, Heterocyclyl oder Heterocy- clyl-Cχ-C4-alkyl, wobei der Phenyl- oder der Heterocy- clylrest der vier letztgenannten Substituenten partiell oder vollstänig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, Cχ-C4-Alkyl, Cχ-C4-Halogenalkyl, Cχ-C -Alkoxy, Cχ-C4 -Halogenalkoxy oder Cχ-C4 -Alkoxycarbonyl;Phenyl, phenyl -Cχ-C 4 -alkyl, heterocyclyl or heterocyclyl-Cχ-C 4 -alkyl, where the phenyl or the heterocyclyl radical of the four last-mentioned substituents can be partially or completely halogenated and / or one to three of the can carry the following radicals: nitro, cyano, Cχ-C 4 -alkyl, Cχ-C 4 -haloalkyl, Cχ-C -alkoxy, Cχ-C 4 -haloalkoxy or Cχ-C 4 -alkoxycarbonyl;

Ri9, R20 Hydroxy, Cχ-C6 -Alkyl, Cχ-C6 -Alkoxy, Phenyl, Phe- nyl -Cχ-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, Cχ-C4 -Alkyl, Cx -C4-Halogen- alkyl, Cχ-C -Alkoxy, Cχ-C4-Halogenalkoxy oder Cx-C4 -Alkoxycarbonyl;R i9 , R 20 hydroxy, Cχ-C 6 alkyl, Cχ-C 6 alkoxy, phenyl, phenyl -Cχ-C 4 alkyl or phenoxy, where the latter three substituents can be partially or completely halogenated and / or can carry one to three of the following radicals: nitro, cyano, Cχ-C 4 -alkyl, Cx -C 4 -haloalkyl, Cχ-C -alkoxy, Cχ-C 4 -haloalkoxy or Cx-C 4 -alkoxycarbonyl;

R2i Cχ-C6-Alkyl, C3-C6 -Alkenyl, C3 -C6-Halogenalkenyl,R 2i Cχ-C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl,

C3-C6 -Cycloalkyl, Cχ-C6 -Alkoxy, C3-C6-Alkenyloxy oderC 3 -C 6 cycloalkyl, Cχ-C 6 alkoxy, C 3 -C 6 alkenyloxy or

Di- (Cχ-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, Cχ-C -Alkoxycarbonyl, Cχ-C4 -Alkylaminocarbonyl, Di- (Cχ-C4 -alkyl) aminocarbonyl oder C3-C6-Cycloalkyl;Di- (Cχ-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, Cχ-C -alkoxycarbonyl, Cχ-C 4 alkylaminocarbonyl, di- (Cχ-C 4 alkyl) aminocarbonyl or C 3 -C 6 cycloalkyl;

Phenyl, Phenyl -Cχ-C4-alkyl, Phenylcarbonyl, Heterocyclyl, Heterocycly-Cχ-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, Cχ-C4-Alkyl, Cx -C4-Halogen- alkyl, Cχ-C4 -Alkoxy oder Cχ-C4 -Halogenalkoxy;Phenyl, phenyl -Cχ-C 4 -alkyl, phenylcarbonyl, heterocyclyl, heterocycly-Cχ-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 to three which may carry the following radicals: nitro, cyano, Cχ-C 4 alkyl, Cx -C 4 haloalkyl, Cχ-C 4 alkoxy or Cχ-C 4 haloalkoxy;

R22 Cχ-Cδ -Alkyl oder C3 -C6-Alkenyl;R 22 is Cχ-C δ alkyl or C 3 -C 6 alkenyl;

p 2, 3 oder 4. Außerordentlich bevorzugt sind die Verbindungen der Formeln I, III bzw. IV mitp 2, 3 or 4. The compounds of the formulas I, III and IV are extraordinarily preferred

R Methyl, Ethyl, Halogen, Methoxy, Methylthio, Methyl - sulfonyl, Nitro, Cyano;R is methyl, ethyl, halogen, methoxy, methylthio, methylsulfonyl, nitro, cyano;

R2 Methyl, Ethyl, gegebenenfalls mit Halogen, Cyano,R 2 is methyl, ethyl, optionally with halogen, cyano,

Nitro substituiertes Phenyl oder gegebenenfalls mit Halogen, Cyano, Nitro substituiertes Phenylsulfonyl;Nitro substituted phenyl or phenylsulfonyl optionally substituted with halogen, cyano, nitro;

R3, R4 Wasserstoff, Cχ-C6-Alkyl, Cχ-C6 -Alkylcarbonyl, gegebenenfalls durch Halogen, Cyano, Nitro substituiertes Phenyl,-R 3 , R 4 are hydrogen, Cχ-C 6 -alkyl, Cχ-C 6 -alkylcarbonyl, phenyl optionally substituted by halogen, cyano, nitro,

R5 Wasserstoff;R 5 is hydrogen;

R6 Wasserstoff, Methyl, Chlor;R 6 is hydrogen, methyl, chlorine;

n 1.n 1.

Ebenso außerordentlich bevorzugt sind die Verbindungen der Formel I, III bzw. IV mitThe compounds of the formula I, III or IV are also extremely preferred

Ri° Hydroxy;Ri ° hydroxy;

Ebenso außerordentlich bevorzugt sind die Verbindungen der Formel I, III bzw. IV mitThe compounds of the formula I, III or IV are also extremely preferred

Ri° Halogen, ORi7, SR17, S02Rl8, OS02Ri8, NR2iR22, ONRl8Ri8 oder N-gebundenes Heterocyclyl, das partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, Cχ-C4 -Alkyl, Cχ-C -Halogenalkyl, Cχ-C -Alkoxy oder Cχ-C4 -Halogenalkoxy;R i ° halogen, OR i7 , SR 17 , S0 2 R l8 , OS0 2 R i8 , NR 2i R 22 , ONR l8 Ri 8 or N-linked heterocyclyl, which can be partially or completely halogenated and / or one to three of the can carry the following radicals: nitro, cyano, Cχ-C 4 alkyl, Cχ-C haloalkyl, Cχ-C alkoxy or Cχ-C 4 haloalkoxy;

Ebenso außerordentlich bevorzugt sind die Verbindungen der Formel I, III bzw. IV mitThe compounds of the formula I, III or IV are also extremely preferred

RU, Ri5 Wasserstoff oder Cχ-C4 -Alkyl;RU, R i5 hydrogen or Cχ-C 4 alkyl;

R12, Ri , R6 Wasserstoff oder Cx-C4 -Alkyl;R 12 , R i , R 6 are hydrogen or Cx-C 4 alkyl;

Ri3 Wasserstoff, Hydroxy, Cχ-C6-Alkyl, Di - (Cχ-C6-alk- oxy) -methyl, (Cχ-C6 -Alkoxy) - (Cχ-C6-alkylthio) -methyl, Di- (Cχ-C6-alkylthio) -methyl, Cχ-C6-Alkylthio,R i3 hydrogen, hydroxy, Cχ-C 6 -alkyl, di - (Cχ-C 6 -alk-oxy) -methyl, (Cχ-C 6 -alkoxy) - (Cχ-C 6 -alkylthio) -methyl, di- (Cχ-C 6 alkylthio) methyl, Cχ-C 6 alkylthio,

Cχ-C6-Halogenalkylthio, Cχ-Cδ -Alkylsulfonyl oder Cx -C6 -Halogenalkyisulfonyl ; insbesondere Wasserstoff, Hydroxy oder Cx -C6-Alkyl ,-Cχ-C 6 haloalkylthio, Cχ-C δ alkylsulfonyl or Cx -C 6 haloalkyl sulfonyl; especially hydrogen, hydroxy or Cx -C 6 alkyl,

oderor

Ri und Ri6 bilden gemeinsam eine Cχ-C4-Alkylkette, die einen bis drei Reste aus folgender Gruppe tragen kann: Halogen, Cχ-C4 -Alkyl oder cχ-C4-Halogenalkyl;Ri and R i6 together form a Cχ-C 4 alkyl chain which can carry one to three radicals from the following group: halogen, Cχ-C 4 alkyl or cχ-C 4 haloalkyl;

insbesondere bilden Ri2 und R16 gemeinsam eine Methylenbrücke aus, die einen oder zwei Reste aus folgender Gruppe tragen kann: Halogen, Cχ-C2-Alkyl oder Cχ-C2-Halogenalkyl;in particular R i2 and R 16 together form a methylene bridge which can carry one or two radicals from the following group: halogen, Cχ-C 2 alkyl or Cχ-C 2 haloalkyl;

oderor

R13 und Ri4 bilden gemeinsam mit dem Kohlenstoff, an dem sie gebunden sind, eine Carbonylgruppe aus;R 13 and R i4 together with the carbon to which they are attached form a carbonyl group;

Ebenso außerordentlich bevorzugt sind die Verbindungen der For- mel Ia.The compounds of the formula Ia are also extremely preferred.

Außerordentlichst bevorzugt sind die Verbindungen der Formel I, III bzw. IV mit R6, Ri°=0H und n=l, insbesondere die Verbindungen III 1 bis III 24 und IV 1 bis IV 24, wobei die Restedefinitionen Ri bis R22, X, 1 und n nicht nur in Kombination miteinander, sondern auch jeweils für sich alleine betrachtet für die erfindungs- gemäßen Verbindungen eine besondere Bedeutung haben. Most preferred are the compounds of the formula I, III or IV with R 6 , R i ° = 0H and n = 1, in particular the compounds III 1 to III 24 and IV 1 to IV 24, the radical definitions R i to R 22 , X, 1 and n not only in combination with one another, but also, viewed individually, are of particular importance for the compounds according to the invention.

Tabelle ATable A

Figure imgf000037_0001
Figure imgf000038_0001
Figure imgf000037_0001
Figure imgf000038_0001

Tabelle 1: Verbindungen III 1.1 - III 1.60Table 1: Compounds III 1.1 - III 1.60

Figure imgf000039_0001
Figure imgf000039_0001

Verbindungen der allgemeinen Formel III 1, in der die Substituenten R1, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle A entsprechen.Compounds of the general formula III 1 in which the substituents R 1 , R 3 and R 6 correspond to one row of Table A for each individual compound.

Tabelle 2: Verbindungen III 2.1 - III 2.60Table 2: Compounds III 2.1 - III 2.60

Figure imgf000039_0002
Figure imgf000039_0002

Verbindungen der allgemeinen Formel III 2, in der die Substituenten R1, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle A entsprechen.Compounds of the general formula III 2 in which the substituents R 1 , R 3 and R 6 correspond to one row of Table A for each individual compound.

Tabelle 3: Verbindungen III 3.1 - III 3.60Table 3: Compounds III 3.1 - III 3.60

Figure imgf000039_0003
Figure imgf000039_0003

Verbindungen der allgemeinen Formel III 3, in der die Substituenten R1, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle A entsprechen. Tabelle 4: Verbindungen III 4.1 - III 4.60Compounds of the general formula III 3 in which the substituents R 1 , R 3 and R 6 correspond to one row of Table A for each individual compound. Table 4: Compounds III 4.1 - III 4.60

Figure imgf000040_0001
Figure imgf000040_0001

Verbindungen der allgemeinen Formel III 4, in der die Substituenten R1, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle A entsprechen.Compounds of the general formula III 4, in which the substituents R 1 , R 3 and R 6 correspond to one row of Table A for each individual compound.

Tabelle 5: Verbindungen III 5.1 - III 5.60Table 5: Compounds III 5.1 - III 5.60

Figure imgf000040_0002
Figure imgf000040_0002

Verbindungen der allgemeinen Formel III 5, in der die Substituenten R1, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle A entsprechen.Compounds of the general formula III 5, in which the substituents R 1 , R 3 and R 6 correspond to one row of Table A for each individual compound.

Tabelle 6: Verbindungen III 6.1 - III 6.60Table 6: Compounds III 6.1 - III 6.60

Figure imgf000040_0003
Figure imgf000040_0003

Verbindungen der allgemeinen Formel III 6, in der die Substituenten R1, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle A entsprechen. Tabelle 7: Verbindungen III 7.1 - III 7.60Compounds of the general formula III 6, in which the substituents R 1 , R 3 and R 6 correspond to one row of Table A for each individual compound. Table 7: Compounds III 7.1 - III 7.60

Figure imgf000041_0001
Figure imgf000041_0001

Verbindungen der allgemeinen Formel III 7, in der die Substituenten R , R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle A entsprechen.Compounds of the general formula III 7, in which the substituents R, R 3 and R 6 correspond to one row of Table A for each individual compound.

Tabelle 8: Verbindungen III 8.1 - III 8.60Table 8: Compounds III 8.1 - III 8.60

Figure imgf000041_0002
Figure imgf000041_0002

Verbindungen der allgemeinen Formel III 8, in der die Substituenten R1, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle A entsprechen.Compounds of the general formula III 8, in which the substituents R 1 , R 3 and R 6 correspond to one row of Table A for each individual compound.

Tabelle 9: Verbindungen III 9.1 - III 9.60Table 9: Compounds III 9.1 - III 9.60

Figure imgf000041_0003
Figure imgf000041_0003

Verbindungen der allgemeinen Formel III 9, in der die Substituenten R1, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle A entsprechen. Tabelle 10: Verbindungen III 10.1 - III 10.60Compounds of the general formula III 9, in which the substituents R 1 , R 3 and R 6 correspond to one row of Table A for each individual compound. Table 10: Compounds III 10.1 - III 10.60

Figure imgf000042_0001
Figure imgf000042_0001

Verbindungen der allgemeinen Formel III 10, in der die Substituenten R1, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle A entsprechen.Compounds of the general formula III 10, in which the substituents R 1 , R 3 and R 6 correspond to one row of Table A for each individual compound.

Tabelle 11: Verbindungen III 11.1 - III 11.60Table 11: Compounds III 11.1 - III 11.60

Figure imgf000042_0002
Figure imgf000042_0002

Verbindungen der allgemeinen Formel III 11, in der die Substituenten R1, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle A entsprechen.Compounds of the general formula III 11, in which the substituents R 1 , R 3 and R 6 correspond to one row of Table A for each individual compound.

Tabelle 12: Verbindungen III 12.1 - III 12.60Table 12: Compounds III 12.1 - III 12.60

Figure imgf000042_0003
Figure imgf000042_0003

Verbindungen der allgemeinen Formel III 12, in der die Substituenten R1, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle A entsprechen. Tabelle 13: Verbindungen III 13.1 - III 13.60Compounds of the general formula III 12 in which the substituents R 1 , R 3 and R 6 correspond to one row of Table A for each individual compound. Table 13: Compounds III 13.1 - III 13.60

Figure imgf000043_0001
Figure imgf000043_0001

Verbindungen der allgemeinen Formel III 13, in der die Substituenten R1, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle A entsprechen.Compounds of the general formula III 13 in which the substituents R 1 , R 3 and R 6 correspond to one row of Table A for each individual compound.

Tabelle 14: Verbindungen III 14.1 - III 14.60Table 14: Compounds III 14.1 - III 14.60

Figure imgf000043_0002
Figure imgf000043_0002

Verbindungen der allgemeinen Formel III 14, in der die Substituenten R1, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle A entsprechen.Compounds of the general formula III 14 in which the substituents R 1 , R 3 and R 6 correspond to one row of Table A for each individual compound.

Tabelle 15: Verbindungen III 15.1 - III 15.60Table 15: Compounds III 15.1 - III 15.60

Figure imgf000043_0003
Figure imgf000043_0003

Verbindungen der allgemeinen Formel III 15, in der die Substituenten R1, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle A entsprechen. Tabelle 16: Verbindungen III 16.1 - III 16.60Compounds of the general formula III 15, in which the substituents R 1 , R 3 and R 6 correspond to one row of Table A for each individual compound. Table 16: Compounds III 16.1 - III 16.60

Figure imgf000044_0001
Figure imgf000044_0001

Verbindungen der allgemeinen Formel III 16, in der die Substituenten R1, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle A entsprechen.Compounds of the general formula III 16, in which the substituents R 1 , R 3 and R 6 correspond to one row of Table A for each individual compound.

Tabelle 17: Verbindungen III 17.1 - III 17.60Table 17: Compounds III 17.1 - III 17.60

Figure imgf000044_0002
Figure imgf000044_0002

Verbindungen der allgemeinen Formel III 17, in der die Substituenten R1, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle A entsprechen.Compounds of the general formula III 17, in which the substituents R 1 , R 3 and R 6 correspond to one row of Table A for each individual compound.

Tabelle 18: Verbindungen III 18.1 - III 18.60Table 18: Compounds III 18.1 - III 18.60

Figure imgf000044_0003
Figure imgf000044_0003

Verbindungen der allgemeinen Formel III 18, in der die Substituenten R1, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle A entsprechen. Tabelle 19: Verbindungen III 19.1 - III 19.60Compounds of the general formula III 18, in which the substituents R 1 , R 3 and R 6 correspond to one row of Table A for each individual compound. Table 19: Compounds III 19.1 - III 19.60

Figure imgf000045_0001
Figure imgf000045_0001

Verbindungen der allgemeinen Formel III 19, in der die Substituenten R1, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle A entsprechen.Compounds of the general formula III 19, in which the substituents R 1 , R 3 and R 6 correspond to one row of Table A for each individual compound.

Tabelle 20: Verbindungen III 20.1 - III 20.60Table 20: Compounds III 20.1 - III 20.60

Figure imgf000045_0002
Figure imgf000045_0002

Verbindungen der allgemeinen Formel III 20, in der die Substituenten R1, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle A entsprechen.Compounds of the general formula III 20 in which the substituents R 1 , R 3 and R 6 correspond to one row of Table A for each individual compound.

Tabelle 21: Verbindungen III 21.1 - III 21.60Table 21: Compounds III 21.1 - III 21.60

Figure imgf000045_0003
Figure imgf000045_0003

Verbindungen der allgemeinen Formel III 21, in der die Substituenten R1, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle A entsprechen. Tabelle 22: Verbindungen III 22.1 - III 22.60Compounds of the general formula III 21 in which the substituents R 1 , R 3 and R 6 correspond to one row of Table A for each individual compound. Table 22: Compounds III 22.1 - III 22.60

Figure imgf000046_0001
Figure imgf000046_0001

Verbindungen der allgemeinen Formel III 22, in der die Substituenten R , R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle A entsprechen.Compounds of the general formula III 22 in which the substituents R, R 3 and R 6 correspond to one row of Table A for each individual compound.

Tabelle 23: Verbindungen III 23.1 - III 23.60Table 23: Compounds III 23.1 - III 23.60

Figure imgf000046_0002
Figure imgf000046_0002

Verbindungen der allgemeinen Formel III 23, in der die Substituenten R1, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle A entsprechen.Compounds of the general formula III 23 in which the substituents R 1 , R 3 and R 6 correspond to one row of Table A for each individual compound.

Tabelle 24: Verbindungen III 24.1 - III 24.60Table 24: Compounds III 24.1 - III 24.60

(4(4th

Figure imgf000046_0003
Figure imgf000046_0003

Verbindungen der allgemeinen Formel III 24, in der die Substituenten R1, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle A entsprechen. Tabelle BCompounds of the general formula III 24 in which the substituents R 1 , R 3 and R 6 correspond to one row of Table A for each individual compound. Table B

Figure imgf000047_0001
Figure imgf000048_0001
Figure imgf000049_0001
Figure imgf000050_0001
Figure imgf000051_0001
Figure imgf000052_0001
Figure imgf000053_0001
Figure imgf000054_0001
Tabelle 25: Verbindungen IV 1.1 - IV 1.300
Figure imgf000047_0001
Figure imgf000048_0001
Figure imgf000049_0001
Figure imgf000050_0001
Figure imgf000051_0001
Figure imgf000052_0001
Figure imgf000053_0001
Figure imgf000054_0001
Table 25: Compounds IV 1.1 - IV 1.300

Figure imgf000055_0001
Figure imgf000055_0001

Verbindungen der allgemeinen Formel IV 1, in der die Substituenten Rl, R2, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle B entsprechen.Compounds of the general formula IV 1, in which the substituents Rl, R 2 , R 3 and R 6 correspond to one row of Table B for each individual compound.

Tabelle 26: Verbindungen IV 2.1 - IV 2.300Table 26: Compounds IV 2.1 - IV 2.300

Figure imgf000055_0002
Figure imgf000055_0002

Verbindungen der allgemeinen Formel IV 2, in der die Substituenten R1, R2, R3 und R6 für jede einzelne Verbindung je- weils einer Zeile der Tabelle B entsprechen.Compounds of the general formula IV 2, in which the substituents R 1 , R 2 , R 3 and R 6 correspond to one row of Table B for each individual compound.

Tabelle 27: Verbindungen IV 3.1 - IV 3.300Table 27: Compounds IV 3.1 - IV 3.300

Figure imgf000055_0003
Figure imgf000055_0003

Verbindungen der allgemeinen Formel IV 3 , in der die Substituenten R1, R2, R3 und R6 für jede einzelne Verbindung je- weils einer Zeile der Tabelle B entsprechen. Tabelle 28: Verbindungen IV 4.1 - IV 4.300Compounds of the general formula IV 3 in which the substituents R 1 , R 2 , R 3 and R 6 correspond to one row of Table B for each individual compound. Table 28: Compounds IV 4.1 - IV 4,300

Figure imgf000056_0001
Figure imgf000056_0001

Verbindungen der allgemeinen Formel IV 4, in der die Substituenten Rx, R2, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle B entsprechen.Compounds of the general formula IV 4, in which the substituents R x , R 2 , R 3 and R 6 correspond to one row of Table B for each individual compound.

Tabelle 29: Verbindungen IV 5.1 - IV 5.300Table 29: Compounds IV 5.1 - IV 5.300

Figure imgf000056_0002
Figure imgf000056_0002

Verbindungen der allgemeinen Formel IV 5, in der die Substituenten R1, R2, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle B entsprechen.Compounds of the general formula IV 5 in which the substituents R 1 , R 2 , R 3 and R 6 correspond to one row of Table B for each individual compound.

Tabelle 30: Verbindungen IV 6.1 - IV 6.300Table 30: Compounds IV 6.1 - IV 6.300

Figure imgf000056_0003
Figure imgf000056_0003

Verbindungen der allgemeinen Formel IV 6, in der die Substituenten R1, R2, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle B entsprechen. Tabelle 31: Verbindungen IV 7.1 - IV 7.300Compounds of the general formula IV 6, in which the substituents R 1 , R 2 , R 3 and R 6 correspond to one row of Table B for each individual compound. Table 31: Compounds IV 7.1 - IV 7.300

Figure imgf000057_0001
Figure imgf000057_0001

Verbindungen der allgemeinen Formel IV 7, in der die Substituenten R1, R2, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle B entsprechen.Compounds of the general formula IV 7, in which the substituents R 1 , R 2 , R 3 and R 6 correspond to one row of Table B for each individual compound.

Tabelle 32: Verbindungen IV 8.1 - IV 8.300Table 32: Compounds IV 8.1 - IV 8.300

Figure imgf000057_0002
Figure imgf000057_0002

Verbindungen der allgemeinen Formel IV 8, in der die Substituenten R1, R2, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle B entsprechen.Compounds of the general formula IV 8, in which the substituents R 1 , R 2 , R 3 and R 6 correspond to one row of Table B for each individual compound.

Tabelle 33: Verbindungen IV 9.1 - IV 9.300Table 33: Compounds IV 9.1 - IV 9.300

Figure imgf000057_0003
Figure imgf000057_0003

Verbindungen der allgemeinen Formel IV 9, in der die Substituenten R1, R2, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle B entsprechen. Tabelle 34: Verbindungen IV 10.1 - IV 10.300Compounds of the general formula IV 9, in which the substituents R 1 , R 2 , R 3 and R 6 correspond to one row of Table B for each individual compound. Table 34: Compounds IV 10.1 - IV 10.300

Figure imgf000058_0001
Figure imgf000058_0001

Verbindungen der allgemeinen Formel IV 10, in der die Substituenten Ri, R2, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle B entsprechen.Compounds of the general formula IV 10, in which the substituents R i , R 2 , R 3 and R 6 correspond to one row of Table B for each individual compound.

Tabelle 35: Verbindungen IV 11.1 - IV 11.300Table 35: Compounds IV 11.1 - IV 11.300

Figure imgf000058_0002
Figure imgf000058_0002

Verbindungen der allgemeinen Formel IV 11, in der die Substituenten R1, R2, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle B entsprechen.Compounds of the general formula IV 11 in which the substituents R 1 , R 2 , R 3 and R 6 correspond to one row of Table B for each individual compound.

Tabelle 36: Verbindungen IV 12.1 - IV 12.300Table 36: Compounds IV 12.1 - IV 12.300

Figure imgf000058_0003
Figure imgf000058_0003

Verbindungen der allgemeinen Formel IV 12, in der die Substituenten R1, R2, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle B entsprechen. Tabelle 37: Verbindungen IV 13.1 - IV 13.300Compounds of the general formula IV 12, in which the substituents R 1 , R 2 , R 3 and R 6 correspond to one row of Table B for each individual compound. Table 37: Compounds IV 13.1 - IV 13.300

Figure imgf000059_0001
Figure imgf000059_0001

Verbindungen der allgemeinen Formel IV 13, in der die Substituenten R1, R2, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle B entsprechen.Compounds of the general formula IV 13, in which the substituents R 1 , R 2 , R 3 and R 6 correspond to one row of Table B for each individual compound.

Tabelle 38: Verbindungen IV 14.1 - IV 14.300Table 38: Compounds IV 14.1 - IV 14.300

Figure imgf000059_0002
Figure imgf000059_0002

Verbindungen der allgemeinen Formel IV 14, in der die Substituenten R1, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle B entsprechen.Compounds of the general formula IV 14 in which the substituents R 1 , R 3 and R 6 correspond to one row of Table B for each individual compound.

Tabelle 39: Verbindungen IV 15.1 - IV 15.300Table 39: Compounds IV 15.1 - IV 15.300

Figure imgf000059_0003
Figure imgf000059_0003

Verbindungen der allgemeinen Formel IV 15, in der die Substituenten R1, R2, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle B entsprechen. Tabelle 40: Verbindungen IV 16.1 - IV 16.300Compounds of the general formula IV 15, in which the substituents R 1 , R 2 , R 3 and R 6 correspond to one row of Table B for each individual compound. Table 40: Compounds IV 16.1 - IV 16.300

Figure imgf000060_0001
Figure imgf000060_0001

Verbindungen der allgemeinen Formel IV 16, in der die Substituenten R1, R2, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle B entsprechen.Compounds of the general formula IV 16, in which the substituents R 1 , R 2 , R 3 and R 6 correspond to one row of Table B for each individual compound.

Tabelle 41: Verbindungen IV 17.1 - IV 17.300Table 41: Compounds IV 17.1 - IV 17.300

Figure imgf000060_0002
Figure imgf000060_0002

Verbindungen der allgemeinen Formel IV 17, in der die Substituenten R1, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle B entsprechen.Compounds of the general formula IV 17, in which the substituents R 1 , R 3 and R 6 correspond to one row of Table B for each individual compound.

Tabelle 42: Verbindungen IV 18.1 - IV 18.300Table 42: Compounds IV 18.1 - IV 18.300

Figure imgf000060_0003
Figure imgf000060_0003

Verbindungen der allgemeinen Formel IV 18, in der die Substituenten R1, R2, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle B entsprechen. Tabelle 43: Verbindungen IV 19.1 - IV 19.300Compounds of the general formula IV 18, in which the substituents R 1 , R 2 , R 3 and R 6 correspond to one row of Table B for each individual compound. Table 43: Compounds IV 19.1 - IV 19.300

Figure imgf000061_0001
Figure imgf000061_0001

Verbindungen der allgemeinen Formel IV 19, in der die Substituenten R1, R2, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle B entsprechen.Compounds of the general formula IV 19, in which the substituents R 1 , R 2 , R 3 and R 6 correspond to one row of Table B for each individual compound.

Tabelle 44: Verbindungen IV 20.1 - IV 20.300Table 44: Compounds IV 20.1 - IV 20.300

Figure imgf000061_0002
Figure imgf000061_0002

Verbindungen der allgemeinen Formel IV 20, in der die Substituenten R1, R2, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle B entsprechen.Compounds of the general formula IV 20, in which the substituents R 1 , R 2 , R 3 and R 6 correspond to one row of Table B for each individual compound.

Tabelle 45: Verbindungen IV 21.1 - IV 21.300Table 45: Compounds IV 21.1 - IV 21.300

(4(4th

Figure imgf000061_0003
Figure imgf000061_0003

Verbindungen der allgemeinen Formel IV 21, in der die Substituenten R1, R2, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle B entsprechen. Tabelle 46: Verbindungen IV 22.1 - IV 22.300Compounds of the general formula IV 21, in which the substituents R 1 , R 2 , R 3 and R 6 correspond to one row of Table B for each individual compound. Table 46: Compounds IV 22.1 - IV 22.300

Figure imgf000062_0001
Figure imgf000062_0001

Verbindungen der allgemeinen Formel IV 22, in der die Substituenten R1, R2, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle B entsprechen.Compounds of the general formula IV 22 in which the substituents R 1 , R 2 , R 3 and R 6 correspond to one row of Table B for each individual compound.

Tabelle 47: Verbindungen IV 23.1 - IV 23.300Table 47: Compounds IV 23.1 - IV 23.300

Figure imgf000062_0002
Figure imgf000062_0002

Verbindungen der allgemeinen Formel IV 23, in der die Substituenten R1, R2, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle B entsprechen.Compounds of the general formula IV 23, in which the substituents R 1 , R 2 , R 3 and R 6 correspond to one row of Table B for each individual compound.

Tabelle 48: Verbindungen IV 24.1 - IV 24.300Table 48: Compounds IV 24.1 - IV 24.300

Verbindungen der allgemeinen Formel IV 24, in der die Substituenten R1, R2, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle B entsprechen. Darstellung von Verbindungen der Formel I mit Ri°=Hydroxy durch Umsetzung einer aktivierten Carbonsäure Va oder einer Carbonsäure Vb, die vorzugsweise in situ aktiviert wird, mit einem Cyclohexandion der Formel XII zu dem Acylierungsprodukt und anschließende Umlagerung.Compounds of the general formula IV 24, in which the substituents R 1 , R 2 , R 3 and R 6 correspond to one row of Table B for each individual compound. Preparation of compounds of the formula I with R i ° = hydroxy by reacting an activated carboxylic acid Va or a carboxylic acid Vb, which is preferably activated in situ, with a cyclohexanedione of the formula XII to give the acylation product and subsequent rearrangement.

Figure imgf000063_0001
Figure imgf000063_0001

XIIXII

Figure imgf000063_0002
Figure imgf000063_0002

I (mi t Ri° = OH) Li steht für eine nucleophil verdrängbare Abgangsgruppe, wie Halogen z.B. Brom oder Chlor, Hetaryl, z.B. Imidazolyl oder Pyridyl, Carboxylat, z.B. Acetat oder Trifluoracetat etc.I (with Ri ° = OH) Li stands for a nucleophilically displaceable leaving group, such as halogen, for example bromine or chlorine, hetaryl, for example imidazolyl or pyridyl, carboxylate, for example acetate or trifluoroacetate etc.

Die aktivierte Benzoesäure Va kann direkt eingesetzt werden, wie im Fall der Benzoylhalogenide oder in situ erzeugt werden, z.B. mit Dicyclohexylcarbodiimid, Triphenylphosphin/Azo- dicarbonsäureester, 2-Pyridindisulfid/Triphenylphosphin, Carbonyldiimidazol etc.The activated benzoic acid Va can be used directly, as in the case of the benzoyl halides, or generated in situ, e.g. with dicyclohexylcarbodiimide, triphenylphosphine / azodicarboxylic acid ester, 2-pyridine disulfide / triphenylphosphine, carbonyldiimidazole etc.

Gegebenenfalls kann es von Vorteil sein, die Acylierungsreak- tion 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 Va bzw. Vb, 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 Va or Vb, can be advantageous.

Als Hilfsbasen eignen sich tertiäre Alkylamme, Pyridin oder Alkalimetallcarbonate. Als Lösungsmittel können z.B. chlo- rierte Kohlenwasserstoffe, wie Methylenchlorid oderSuitable auxiliary bases are tertiary alkylammes, pyridine or alkali metal carbonates. As a solvent e.g. chlorinated hydrocarbons, such as methylene chloride or

1, 2-Dichlorethan, aromatische Kohlenwasserstoffe, wie Toluol, Xylol oder Chlorbenzol, Ether, wie Diethylether, Methyl- tert .-butylether, Tetrahydrofuran oder Dioxan, polare aprotische Lösungsmittel, wie Acetonitril, Dimethylformamid oder Dimethylsulfoxid oder Ester wie Essigsäureethylester oder Gemische hiervon verwendet werden.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 become.

Werden Benzoylhalogenide als aktivierte Carbonsäurekomponente eingesetzt, so kann es zweckmäßig sein, bei Zugabe dieses Reaktionspartners die Reaktionsmischung auf 0-10°C abzukühlen. Anschließend rührt man bei 20 - 100°C, vorzugsweise bei 25 - 50°C, bis die Umsetzung vollständig ist. Die Aufarbeitung erfolgt in üblicher Weise, z.B. wird das Reaktionsgemisch auf Wasser gegossen, 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 Ümlagerung eingesetzt werden.If benzoyl halides are used as the activated carboxylic acid component, it may be expedient to cool the reaction mixture to 0-10 ° C. when this reactant is added. The mixture is then stirred at 20-100 ° C., preferably at 25-50 ° C., until the reaction is complete. The 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 the rearrangement without further purification.

Die ümlagerung 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. Als Lösungsmittel können z.B. Acetonitril, Methylenchlorid, 1, 2-Dichlorethan, Dioxan, Essigsäureethylester, Toluol oder Gemische hiervon verwendet werden. Bevorzugte Lösungsmittel sind Acetonitril und Dioxan.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. 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.

Geeignete Basen sind tertiäre Amine wie Triethylamin, aromatische Amine wie Pyridin oder Alkalicarbonate, wie Natrium- carbonat 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.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 Natriumcyanid oder Kaliumcyanid und organische Cyanoverbindungen, wie Acetoncyanhydrin oder Trimethylsilylcyanid in Betracht. Sie werden in einer Menge von 1 bis 50 Molprozent, bezogen auf den Ester, eingesetzt. Vorzugsweise werden Acetoncyanhydrin oder Trimethylsilylcyanid, z.B. in einer Menge von 5 bis 15, vorzugsweise etwa 10 Molprozent, 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 mole percent, based on the ester. Preferably acetone cyanohydrin or trimethylsilyl cyanide, e.g. in an amount of 5 to 15, preferably about 10 mole percent, 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 Alkalicarbonatlösung, 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.

Darstellung von Verbindungen der Formel I mit R10 = Halogen durch Umsetzung von tricyclischen Cyclohexandionderivaten derRepresentation of compounds of formula I with R 10 = halogen by reaction of tricyclic cyclohexanedione derivatives

Formel I (mit R10 = Hydroxy) mit Halogenierungsmitteln:Formula I (with R 10 = hydroxy) with halogenating agents:

Figure imgf000065_0001
Figure imgf000065_0001

I (mit Rl° = OH) Als Halogenierungsmittel eignen sich beispielsweise Phosgen, Diphosgen, Triphosgen, Thionylchlorid, Oxalylchlorid, Phosphoroxychlorid, Phosphorpentachlorid, Mesylchlorid, Chlormethylen-N,N-dimethylammoniumchlorid, Oxalylbromid, Phosphoroxybromid etc.I (with R l ° = OH) 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.

Darstellung von Verbindungen der Formel I mit R10 = ORi7, OS02Ri8, OPORi9R20 oder OPSRi9R20 durch Umsetzung von tricyclischen Cyclohexandionderivaten der Formel I (mit R10 = Hydroxy) mit Alkylierungs- , Sulfonylierungs- bzw. Phosphonylierungs- mitteln Aα, Aß, Aγ bzw. Aδ.Preparation of compounds of the formula I with R 10 = OR i7 , OS0 2 R i8 , OPORi 9 R 20 or OPSR i9 R 20 by reacting tricyclic cyclohexanedione derivatives of the formula I (with R 10 = hydroxy) with alkylation, sulfonylation or Phosphonylating agents Aα, Aß, Aγ and Aδ.

Figure imgf000066_0001
Figure imgf000066_0001

L2 - PSRi9R20 Aδ L 2 - PSRi 9 R 2 0 Aδ

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. B. chlorine or bromine, hetaryl, e.g. B. imidazolyl, carboxylate, e.g. B. acetate, or sulfonate, e.g. B. mesylate or triflate etc.

Die Verbindungen der Formel Aα, Aß, Aγ oder Aδ können direkt eingesetzt werden wie z. B. im Fall der Carbonsaurehalogenide oder in situ erzeugt werden, z. B. aktivierte Carbonsäuren (mit Carbonsäure und Dicyclohexylcarbodiimid etc.).The compounds of formula Aα, Aß, Aγ or Aδ can be used directly, such as. B. in the case of carboxylic acid halides or generated in situ, for. B. activated carboxylic acids (with carboxylic acid and dicyclohexylcarbodiimide etc.).

D. Darstellung von Verbindungen der Formel I mit R10 = ORi"7, SRi?, PORi9R20, NR2iR22, ONR18Ri8 oder N-gebundenes Heterocyclyl durch Umsetzung von Verbindungen der Formel I mit Ri0 = Halogen, OS02R 8 mit Verbindungen der Formel Bα, Bß, Bγ, Bδ, Bε oder Bη, gegebenenfalls in Gegenwart einer Base oder unter voran- gehender Salzbildung. HORl"7 Bα oder la und/oder Ib (mit la und/oder Ib R17 = 0RI7, SRi7,D. Preparation of compounds of the formula I with R 10 = OR i "7 , SR i?, POR i9 R 20 , NR 2i R 22 , ONR 18 R i8 or N-linked heterocyclyl by reacting compounds of the formula I with R i0 = Halogen, OS0 2 R 8 with compounds of the formula Bα, Bß, Bγ, Bδ, Bε or Bη, optionally in the presence of a base or with previous salt formation. HOR l "7 Bα or la and / or Ib (with la and / or Ib R 17 = 0RI 7 , SRi 7 ,

PO 19R20 , NR21R22 , (mit Ri° = Halogen, HSRi7 Bß OS02R18) oder ONRiδRis oder N- gebundenesPO 19R20, NR 21 R 22, (with R i ° = halogen, HSRi 7 Bß OS0 2 R 18 ) or ONRiδRis or N-bound

HPORl9R20 Bγ Heterocyclyl ) oderHPOR 19 R 20 Bγ heterocyclyl) or

HNR lR22 Bδ oderHNR lR 22 Bδ or

HONRlSRl8 Bε oderHONR l SRl 8 Bε or

H (N-gebundenes Bη Heterocyclyl)H (N-linked Bη heterocyclyl)

Darstellung von Verbindungen der Formel I mit R10 = SORi8, SO2RI8 durch Umsetzung von Verbindungen der Formel I mit Rio - 5R18 mj_t einem Oxidationsmittel .Representation of compounds of formula I with R 10 = SOR i8 , SO 2 RI 8 by reaction of compounds of formula I with Rio - 5R18 m j_ t an oxidizing agent.

la und/oder Ib Oxidationsmittel la und/oder Ib (mit Ri° = SR8) (mit Rl° = SORi8, S02R18)la and / or Ib oxidizing agent la and / or Ib (with R i ° = SR 8 ) (with R l ° = SOR i8 , S0 2 R 18 )

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.

Die Herstellung der Verbindungen der Formel V erfolgt durch Oxi- dation der Verbindungen der Formel XIII mit Oxidationsmitteln:The compounds of the formula V are prepared by oxidation of the compounds of the formula XIII using oxidizing agents:

Figure imgf000067_0001
wobei T Cχ-C -Alkoxy bedeutet und die übrigen Substituenten die oben beschriebene Bedeutung haben.
Figure imgf000067_0001
where T is Cχ-C -alkoxy and the other substituents have the meaning described above.

Als Oxidationsmittel eignen sich bspw. m-Chlorperbenzoesäure, Peroxyessigsäure oder Wasserstoffperoxid, ggf. in Gegenwart eines Katalysators wie Wolframat. Die Darstellung von Verbindungen der Formel Xllla erfolgt durch dipolare Cycloaddition von Verbindungen der Formel XIV in Gegenwart eines Oxidationsmittels (s. z.B. Kim, J.N. et.al. Synth. Commun. 1990, 20, 1373; Hassner, A. et. al. Synthesis 1989, 57; Kellabennani, A.E. et. al . Tetrahedron 1995, 51, 10923),Suitable oxidizing agents are, for example, m-chloroperbenzoic acid, peroxyacetic acid or hydrogen peroxide, if appropriate in the presence of a catalyst such as tungsten. Compounds of the formula Xllla are prepared by dipolar cycloaddition of compounds of the formula XIV in the presence of an oxidizing agent (see, for example, Kim, JN et.al. Synth. Commun. 1990, 20, 1373; Hassner, A. et. Al. Synthesis 1989, 57; Kellabennani, AE et al. Tetrahedron 1995, 51, 10923),

Figure imgf000068_0001
XIV Xllla
Figure imgf000068_0001
XIV Xllla

wobei T Cχ-C -Alkoxy bedeutet und die übrigen Substituenten die oben beschriebenen Bedeutungen haben.where T is Cχ-C -alkoxy and the other substituents have the meanings described above.

Als Oxidationsmittel kommen z.B. Chloramin T oder Natriumhypo- chlorit zur Anwendung.As oxidizing agents come e.g. Chloramine T or sodium hypochlorite are used.

Die Darstellung von Verbindungen der Formel Xlllb erfolgt durch Cycloaddition von Verbindungen der Formel XV (s. z.B. Bishop, J.E. et. al. J. Chem. Soc. Perk. Trans. 1, 1995, 2551; Shimizu, T. et. al. Bull, Chem. Soc. Jpn. 1980, 53, 429; Grigg, R. et. al. Tetrahedron 1987, 43, 5873),Compounds of the formula X11b are prepared by cycloaddition of compounds of the formula XV (see, for example, Bishop, JE et. Al. J. Chem. Soc. Perk. Trans. 1, 1995, 2551; Shimizu, T. et. Al. Bull, Chem. Soc. Jpn. 1980, 53, 429; Grigg, R. et. Al. Tetrahedron 1987, 43, 5873),

Figure imgf000068_0002
Figure imgf000068_0002

XIIlb

Figure imgf000068_0003
XIIlb
Figure imgf000068_0003

worin T Cχ-C4 -Alkoxy bedeutet und die übrigen Substituenten die oben beschriebene Bedeutung haben.wherein T is Cχ-C 4 alkoxy and the other substituents have the meaning described above.

Die Darstellung der Oxime XIV erfolgt nach allgemein bekannten Methoden aus den Aldehyden XVI (s. March, J. Advanced Organic Chemistry, 4. Ed., Wiley and Sons 1992, S. 906 ff.).

Figure imgf000069_0001
The oximes XIV are prepared using generally known methods from the aldehydes XVI (see March, J. Advanced Organic Chemistry, 4th Ed., Wiley and Sons 1992, pp. 906 ff.).
Figure imgf000069_0001

worin T Cχ-C -Alkoxy bedeutet und die übrigen Substituenten die oben beschriebene Bedeutung haben.wherein T is Cχ-C -alkoxy and the other substituents have the meaning described above.

Die Darstellung der Hydrazone XV erfolgt nach allgemein bekannten Methoden aus den Aldehyden XVI (s. March, J. Advanced Organic Chemistry, 4. Ed., Wiley, 1992, S. 904 ff.).The hydrazone XV is represented by generally known methods from the aldehydes XVI (see March, J. Advanced Organic Chemistry, 4th Ed., Wiley, 1992, pp. 904 ff.).

Figure imgf000069_0002
Figure imgf000069_0002

worin T Cχ-C4 -Alkoxy bedeutet und die übrigen Substituenten die oben beschriebene Bedeutung haben.wherein T is Cχ-C 4 alkoxy and the other substituents have the meaning described above.

Die Darstellung von Verbindungen der Formel XVI erfolgt durch nu- kleophile aromatische Substitution von Verbindungen der Formel XVII mit substituierten Allylthiolen in polaren Lösungsmitteln in Gegenwart von Basen. Als Basen können tertiäre Amine wie Triethylamin oder Pydridin oder Alkalimetallcarbonate wie Lithium- carbonat oder Natriumcarbonat eingesetzt werden.

Figure imgf000070_0001
Compounds of the formula XVI are prepared by nucleophilic aromatic substitution of compounds of the formula XVII with substituted allyl thiols in polar solvents in the presence of bases. Tertiary amines such as triethylamine or pydridine or alkali metal carbonates such as lithium carbonate or sodium carbonate can be used as bases.
Figure imgf000070_0001

Als Lösungsmittel eignen sich Methanol, Ethanol, Dimethylformamid oder N-Methyl-pyrrolidon.Methanol, ethanol, dimethylformamide or N-methyl-pyrrolidone are suitable as solvents.

Die Aldehyde der Formel XVII sind bekannt aus beispielsweise der WO 98/31681. The aldehydes of the formula XVII are known from, for example, WO 98/31681.

Herstellung der AusgangsεtoffeProduction of the starting materials

a) Synthese von 2-Chlor-3 -formyl -4-allylthio-benzoesäure- methylestera) Synthesis of 2-chloro-3-formyl -4-allylthio-benzoic acid methyl ester

Zu einer Lösung aus Li2C03 (8,8 g, 119 mmol) undTo a solution of Li 2 CO 3 (8.8 g, 119 mmol) and

2 -Chlor -3 -formyl -4 -methylsulfonyl -benzoesäuremethylester2 -Chlor -3 -formyl -4 -methylsulfonyl -benzoic acid methyl ester

(30 g, 108,5 mmol) in EtOH (300 ml) wird Allylthiol (11,5 g, 108,5 mmol) getropft und das Gemisch 12 h unter(30 g, 108.5 mmol) in EtOH (300 ml), allyl thiol (11.5 g, 108.5 mmol) is added dropwise and the mixture under for 12 h

Rückfluß erhitzt. Man engt am Rotationsverdampfer ein, nimmt den Rückstand in Wasser/Ethylacetat auf, wäscht die organische Phase mit Wasser, trocknet über Na S04 und entfernt das Lösungsmittel. Der braune Rückstand wird an Kieselgel mit Cyclohexan/Ethylacetat (4 : 1) als Eluent chromatografiert .Reflux heated. It is concentrated on a rotary evaporator, the residue is taken up in water / ethyl acetate, the organic phase is washed with water, dried over Na S0 4 and the solvent is removed. The brown residue is chromatographed on silica gel with cyclohexane / ethyl acetate (4: 1) as the eluent.

Ausbeute: 16,8 g (57 %) gelbes ÖlYield: 16.8 g (57%) yellow oil

iHNMR δ 10,7 (s, 1H) , 7,86 (d, 1H) , 7,30 (d, 1H) , i HNMR δ 10.7 (s, 1H), 7.86 (d, 1H), 7.30 (d, 1H),

5,90 (m, 1H) , 5,33 (m, 2H) , 3,95 (s, 3H) , 3,63 (d, 2H) .5.90 (m, 1H), 5.33 (m, 2H), 3.95 (s, 3H), 3.63 (d, 2H).

b) Synthese von 2 -Chlor - 3 -hydroxyiminomethyl - 4 - allylthio- benzoesäuremethylesterb) Synthesis of 2-chloro-3-hydroxyiminomethyl-4-allylthio-benzoic acid methyl ester

Zu einer Lösung des Methylesters aus Stufe a) (15,85 g, 58,6 mmol) und Na C03 (3,5 g, 33 mmol) in Ethanol (200 ml) wird Hydroxylammoniumchlorid (4,48 g, 64,5 mmol) zugesetzt und der Ansatz übers Wochenende bei RT gerührt. Man gibt Wasser (200 ml) zu und rührt eine weitere Stunde bevor das Gemisch am Rotationsverdampfer eingeengt wird. Der Rückstand wird in Wasser/Ethylacetat aufgenommen, die organische Phase über Na2S04 getrocknet und das Lösungsmittel entfernt. Man erhält das Oxim quantitativ als hel- len Sirup.Hydroxylammonium chloride (4.48 g, 64.5) is added to a solution of the methyl ester from stage a) (15.85 g, 58.6 mmol) and Na CO 3 (3.5 g, 33 mmol) in ethanol (200 ml) mmol) was added and the mixture was stirred at RT over the weekend. Water (200 ml) is added and the mixture is stirred for a further hour before the mixture is concentrated on a rotary evaporator. The residue is taken up in water / ethyl acetate, the organic phase is dried over Na 2 S0 4 and the solvent is removed. The oxime is obtained quantitatively as a light syrup.

iHNMR δ 8,51 (s, 1H) , 8,39 (s, 1H) , 7,73 (d, 1H) , 7,28 (s, 1H) , 5,88 (m, 1H) , 5,25 (m, 2H) , 3,93 (s, 3H) , 3,60 i HNMR δ 8.51 (s, 1H), 8.39 (s, 1H), 7.73 (d, 1H), 7.28 (s, 1H), 5.88 (m, 1H), 5, 25 (m, 2H), 3.93 (s, 3H), 3.60

(d, 2H) Herstellung der Zwischenprodukte(d, 2H) Manufacture of intermediates

c) Synthese von 9 -Chlor -4H- thiochromano [4, 3 -c] isoxazolin- 8- carbonsäuremethylesterc) Synthesis of 9-chloro-4H-thiochromano [4, 3-c] isoxazoline-8-carboxylic acid methyl ester

Zu einer Lösung der Verbindung aus Stufe b) (16,3 g, 57 mmol) und einer Spatelspitze NaOAc in CH2C1 (300 ml) wird eine wäßrige NaOCI-Lsg. (12,5 %, 40,8 g, 68,4 mmol) getropft und der Ansatz 6 h unter Rückfluß erhitzt. Nach dem Erkalten trennt man die organische Phase ab, wäscht mit Wasser, trocknet über Na2S0 und entfernt das Lösungsmittel. Die säulenchromatografische Reinigung des Rückstandes liefert das Produkt in Form farbloser Kristalle.To a solution of the compound from step b) (16.3 g, 57 mmol) and a spatula tip of NaOAc in CH 2 C1 (300 ml), an aqueous NaOCI solution. (12.5%, 40.8 g, 68.4 mmol) were added dropwise and the mixture was heated under reflux for 6 h. After cooling, the organic phase is separated off, washed with water, dried over Na 2 S0 and the solvent is removed. Column chromatographic purification of the residue gives the product in the form of colorless crystals.

Ausbeute: 8,4 g (52 %)Yield: 8.4 g (52%)

iHNMR δ 7,57 (d, 1H) , 7,17 (d, 1H) , 4,64 (t, 1H) , 4,28 (t, 1H) , 3,93 (s, 3H) , 3,72 (m, 2H) , 3,30 (t, 1H) , 3,10 (m, 1H) . i HNMR δ 7.57 (d, 1H), 7.17 (d, 1H), 4.64 (t, 1H), 4.28 (t, 1H), 3.93 (s, 3H), 3, 72 (m, 2H), 3.30 (t, 1H), 3.10 (m, 1H).

d) Synthese von 9-Chlor-4H- thiochromano [4, 3 -c] isoxazolin- 8- carbonsäured) Synthesis of 9-chloro-4H-thiochromano [4, 3-c] isoxazoline-8-carboxylic acid

Der Methylester aus Stufe c) (7,3 g, 25,7 mmol) in 200 ml Methanol und 200 ml Wasser wurde mit NaOH (1,56 g, 39 mmol) versetzt und 4 h unter Rückfluß erhitzt. Das Methanol wurde entfernt und die wäßrige Phase mit Ether extrahiert. Dann säuerte man mit HC1 (konz . ) an, extra- hierte mit Ethylacetat, trocknete über Na S04 und entfernte das Solvens.The methyl ester from step c) (7.3 g, 25.7 mmol) in 200 ml of methanol and 200 ml of water was mixed with NaOH (1.56 g, 39 mmol) and heated under reflux for 4 h. The methanol was removed and the aqueous phase extracted with ether. Then acidified with HC1 (conc.), Extracted with ethyl acetate, dried over Na S0 4 and the solvent was removed.

Ausbeute: 6,75 g (97 %)Yield: 6.75 g (97%)

HNMR (DMSO) δ 7,62 (d, 1H) , 7,38 (d, 1H) , 9,56 (dd, 1H) ,HNMR (DMSO) δ 7.62 (d, 1H), 7.38 (d, 1H), 9.56 (dd, 1H),

4,20 (dd, 1H) , 3,80 (m, 1H) , 3,32 (m, 2H) .4.20 (dd, 1H), 3.80 (m, 1H), 3.32 (m, 2H).

e) Synthese von 9-Chlor-5, 5-dioxo-4H- thiochromano [4, 3 -c] - isoxazolin- 8 - carbonsäuree) Synthesis of 9-chloro-5, 5-dioxo-4H-thiochromano [4, 3-c] - isoxazoline-8-carboxylic acid

Die Säure aus Stufe d) (4,4 g, 16,3 mmol) wurde in 30 ml Eisessig gelöst und mit einer Spatelspitze Natriumwolframat versetzt. Danach tropfte man bei 50°C Perhydrol (4,16 g, 36,7 mmol) zu und rührte weitere 4 h bei 50°C. Man rührte in Eiswasser ein und extrahierte mit Ethyl- acetat. Die organische Phase wurde mit Wasser gewaschen, über Natriumsulfat getrocknet und eingeengt.The acid from step d) (4.4 g, 16.3 mmol) was dissolved in 30 ml of glacial acetic acid and a spatula tip of sodium tungstate was added. Thereafter, perhydrol (4.16 g, 36.7 mmol) was added dropwise at 50 ° C. and the mixture was stirred at 50 ° C. for a further 4 h. The mixture was stirred into ice water and extracted with ethyl acetate. The organic phase was washed with water, dried over sodium sulfate and concentrated.

Ausbeute: 64 % (3,15 g) Schmp.: 225-227°C.Yield: 64% (3.15 g) mp: 225-227 ° C.

III Herstellung der EndprodukteIII Manufacture of the end products

f ) 2 - { (9 -Chlor -5, 5-dioxo-4H- thiochromano [4 , 3 -c] isoxazolin- 8 -yl) -carbonyl} - 1 -hydroxy-cyclohex-1-en-3 -onf) 2 - {(9-Chloro -5, 5-dioxo-4H-thiochromano [4, 3-c] isoxazolin-8 -yl) -carbonyl} - 1 -hydroxy-cyclohex-1-en-3 -one

Zu einer Lösung aus der Säure aus Stufe e) (0,37 g, 1,2 mmol) und 1, 3 -Cyclohexandion (0,14 g, 1,2 mmol) in 20 ml Acetonitril gab man 0,25 g (1,2 mmol) N,N-Dicyclo- hexylcarbodiimid und rührte bei Raumtemperatur über Nacht. Dann versetzte man mit Triethylamin (0,25 g, 2,5 mmol) und 0,2 ml Trimethylsilylcyanid und rührte weitere 3 h bei Raumtemperatur. Man fügte je 50 ml Ethyl - acetat und 2 Teile Sodalösung zu und filtrierte vom Feststoff. Die wäßrige Phase wird mit Ξther extrahiert und dann mit HCl (konz.) auf pH3 eingestellt. Man saugte die sich bildenden Kristalle ab.To a solution of the acid from stage e) (0.37 g, 1.2 mmol) and 1,3-cyclohexanedione (0.14 g, 1.2 mmol) in 20 ml acetonitrile was added 0.25 g (1st , 2 mmol) N, N-dicyclohexylcarbodiimide and stirred at room temperature overnight. Triethylamine (0.25 g, 2.5 mmol) and 0.2 ml of trimethylsilyl cyanide were then added and the mixture was stirred at room temperature for a further 3 h. 50 ml each of ethyl acetate and 2 parts of sodium carbonate solution were added and the solid was filtered off. The aqueous phase is extracted with ether and then adjusted to pH 3 with HCl (conc.). The crystals formed were suctioned off.

Ausbeute: 0,2 g, Schmp.: 220°C.Yield: 0.2 g, mp: 220 ° C.

Tabelle 49Table 49

Figure imgf000073_0001
Figure imgf000073_0001

Figure imgf000073_0002
Figure imgf000074_0001
Figure imgf000073_0002
Figure imgf000074_0001

Die Verbindungen I und deren landwirtschaftlich brauchbaren Salze eignen sich - sowohl als Isomerengemische als auch in Form der reinen Isomeren - als Herbizide. Die I enthaltenden herbiziden 1C Mittel bekämpfen Pflanzenwuchs auf Nichtkulturflächen sehr gut, besonders bei hohen Aufwandmengen. In Kulturen wie Weizen, Reis, Mais, Soja und Baumwolle wirken sie gegen Unkräuter und Schad- gräser, ohne die Kulturpflanzen nennenswert zu schädigen. Dieser Effekt tritt vor allem bei niedrigen Aufwandmengen auf.The compounds I and their agriculturally useful salts are suitable - both as isomer mixtures and in the form of the pure isomers - as herbicides. The I-containing 1C herbicides control vegetation very well on nonculture areas, especially at high application rates. In crops such as wheat, rice, maize, soybeans and cotton, they work against weeds and grass weeds without causing any significant damage to crops. This effect occurs especially at low application rates.

1515

In Abhängigkeit von der jeweiligen Applikationsmethode können die Verbindungen I bzw. sie enthaltende Mittel noch in einer weiteren Zahl von Kulturpflanzen zur Beseitigung unerwünschter Pflanzen eingesetzt werden. In Betracht kommen beispielsweise folgendeDepending on the particular application method, the compounds I or compositions containing them can also be used in a further number of crop plants for eliminating undesired plants. For example, the following are considered

20 Kulturen:20 cultures:

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 li on, 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 li on, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea libericaus), Cucumodison dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum,

30 (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.ru- stica) , Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylestre, Ricinus communis, Saccharum officinarum, Seeale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgäre) , Theobroma cacao, Trifolium pratense,30 (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgäre, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopentaici, Manus spec , Nicotiana tabacum (N.ru- stica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylestre, Ricinus communis, Saccharum officinarum, Seeale cereale, Solanum tuberosum, Sorghum bicolor (see vulgar), Theobroma cacao, Trifolium pratense,

40 Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera, Zea mays .40 Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera, Zea mays.

Darüber hinaus können die Verbindungen I auch in Kulturen, die durch Züchtung einschließlich gentechnischer Methoden gegen die 5 Wirkung von Herbiziden tolerant sind, verwandt werden. Die Applikation der herbiziden Mittel bzw. der Wirkstoffe kann im Vorauflauf- oder im Nachauflauf erfahren erfolgen. Sind die Wirkstoffe für gewisse Kulturpflanzen weniger verträglich, so können Ausbringungstechniken angewandt werden, bei welchen die herbiziden Mittel mit Hilfe der Spritzgeräte so gespritzt werden, daß die Blätter der empfindlichen Kulturpflanzen nach Möglichkeit nicht getroffen werden, während die Wirkstoffe auf die Blätter darunter wachsender unerwünschter Pflanzen oder die unbedeckte Bodenfläche gelangen (post-directed, lay-by) .Moreover, the compounds I can also be used in crops which are tolerant by breeding including genetic engineering methods the 5 action of herbicides are used. The herbicidal compositions or the active compounds can be applied in the pre-emergence or in the post-emergence. If the active ingredients are less compatible for certain crop plants, application techniques can be used in which the herbicidal compositions are sprayed with the aid of sprayers in such a way that the leaves of the sensitive crop plants are not hit wherever possible, while the active ingredients are applied to the leaves of undesirable plants growing below them or the uncovered floor area (post-directed, lay-by).

Die Verbindungen I bzw. die sie enthaltenden herbiziden Mittel können beispielsweise in Form von direkt versprühbaren wäßrigen Lösungen, Pulvern, Suspensionen, auch hochprozentigen wäßrigen, öligen oder sonstigen Suspensionen oder Dispersionen, Emulsionen, Oldispersionen, Pasten, Stäubemitteln, Streumitteln oder Granulaten durch Versprühen, Vernebeln, Verstäuben, Verstreuen oder Gießen angewendet werden. Die Anwendungsformen richten sich nach den Verwendungszwecken; sie sollten in jedem Fall möglichst die feinste Verteilung der erfindungsgemäßen Wirkstoffe gewährleisten.The compounds I or the herbicidal compositions comprising them can be sprayed or atomized, for example in the form of directly sprayable aqueous solutions, powders, suspensions, including high-strength aqueous, oily or other suspensions or dispersions, emulsions, old-dispersions, pastes, dusts, sprays or granules , Dusting, scattering or pouring. The application forms depend on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.

Als inerte Zusatzstoffe kommen im Wesentlichen in Betracht: Mineralölfraktionen von mittlerem bis hohem Siedepunkt, wie Kero- sin oder Dieselöl, ferner Kohlenteeröle sowie Öle pflanzlichen oder tierischen Ursprungs, aliphatische, cyclische und aroma- tische Kohlenwasserstoffe, z.B. Paraffin, Tetrahydronaphthalin, alkylierte Naphthaline oder deren Derivate, alkylierte Benzole oder deren Derivate, Alkohole wie Methanol, Ethanol, Propanol, Butanol, Cyclohexanol, Ketone wie Cyclohexanon oder stark polare Lösungsmittel, z. B. Amine wie N-Methylpyrrolidon oder Wasser.The following are essentially considered as inert additives: mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, alkylated benzenes or their derivatives, alcohols such as methanol, ethanol, propanol, butanol, cyclohexanol, ketones such as cyclohexanone or strongly polar solvents, e.g. B. amines such as N-methylpyrrolidone or water.

Wäßrige Anwendungsformen können aus Emulsionskonzentraten, Suspensionen, Pasten, netzbaren Pulvern oder wasserdispergier- baren Granulaten durch Zusatz von Wasser bereitet werden. Zur Herstellung von Emulsionen, Pasten oder Oldispersionen können die tricyclischen Cyclohexandionderivate als solche oder in einem Öl oder Lösungsmittel gelöst, mittels Netz-, Haft-, Dispergier- oder Emulgiermittel in Wasser homogenisiert werden. Es können aber auch aus wirksamer Substanz, Netz-, Haft-, Dispergier- oder Emulgiermittel und eventuell Lösungsmittel oder Öl bestehende Konzentrate hergestellt werden, die zur Verdünnung mit Wasser geeignet sind.Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water. To prepare emulsions, pastes or old dispersions, the tricyclic cyclohexanedione derivatives as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers. However, it is also possible to prepare concentrates consisting of an active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil, which are suitable for dilution with water.

Als oberflächenaktive Stoffe kommen die Alkali-, Erdalkali-, Ammoniumsalze von aromatischen Sulfonsäuren, z.B. Lignin-, Phenol-, Naphthalin- und Dibutylnaphthalinsulfonsäure, sowie von Fettsäuren, Alkyl- und Alkylarylsulfonaten, Alkyl-, Laurylether- und Fettalkoholsulfaten, sowie Salze sulfatierter Hexa-, Hepta- und Octadecanolen sowie von Fettalkoholglykolether , Kondensationsprodukte von sulfoniertem Naphthalin und seiner Derivate mit Formaldehyd, Kondensationsprodukte des Naphthalins bzw. der Naphthalinsulfonsäuren mit Phenol und Formaldehyd, Polyoxy- ethylenoctylphenolether, ethoxyliertes Isooctyl-, Octyl- oder Nonylphenol, Alkylphenyl-, Tributylphenylpolyglykolether, Alkyl - arylpolyetheralkohole, Isotridecylalkohol, Fettalkoholethyleno- xid-Kondensate, ethoxyliertes Rizinusöl, Polyoxyethylenalkylether oder Polyoxypropylenalkylether, Laurylalkoholpolyglykolether- acetat, Sorbitester, Lignin-Sulfitablaugen oder Methylcellulose in Betracht.The surface-active substances are the alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic acids, for example lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa- , Hepta and octadecanols and fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl or nonylphenol, alkylphenyl, arylphenyl, arylphenyl, arylphenyl, arylphenyl, arylphenyl, arylphenyl, arylphenyl, arylphenyl, arylphenyl, arylphenyl, arylphenyl, arylphenol, Isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ether or polyoxypropylene alkyl ether, lauryl alcohol polyglycol ether acetate, sorbitol ester, lignin sulfite liquor or methyl cellulose.

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 Kiesel - säuren, 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 earths such as silica, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, Ammonium nitrate, ureas and vegetable products such as corn flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.

Die Konzentrationen der Wirkstoffe I 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 Wirkstoffs. Die Wirkstoffe werden dabei in einer Reinheit von 90% bis 100%, vorzugsweise 95% bis 100% (nach NMR-Sektrum) eingesetzt.The concentrations of the active ingredients I in the ready-to-use preparations can be varied over a wide range. The formulations generally contain 0.001 to 98% by weight, preferably 0.01 to 95% by weight, of at least one active ingredient. The active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).

Die erfindungsgemäßen Verbindungen I können beispielsweise wie folgt formuliert werden:The compounds I according to the invention can be formulated, for example, as follows:

I 20 Gewichtsteile der Verbindung Nr. 49.1 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. 49.1 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 out and finely distributing the solution in 100,000 parts by weight of water an aqueous dispersion is obtained which contains 0.02% by weight of the active ingredient.

II 20 Gewichtsteile der Verbindung Nr. 49.1 werden in einer Mischung gelöst, die aus 40 Gewichtsteilen Cyclohexanon,II 20 parts by weight of compound no. 49.1 are dissolved in a mixture consisting of 40 parts by weight of cyclohexanone,

30 Gewichtsteilen Isobutanol, 20 Gewichtsteilen des Anlage- rungsproduktes von 7 Mol Ethylenoxid an 1 Mol Isooctylphenol und 10 Gewichtsteilen des Anlagerungsproduktes von 40 Mol Ethylenoxid an 1 Mol Ricinusöl besteht. Durch Eingießen und feines Verteilen der Lösung in 100 000 Gewichtsteilen Wasser erhält man eine wäßrige Dispersion, die 0,02 Gew. % des Wirkstoffs enthält.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 and 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active ingredient.

III 20 Gewichtsteile des Wirkstoffs Nr. 49.1 werden in einer Mischung gelöst, die aus 25 Gewichtsteilen Cyclohexanon,III 20 parts by weight of active ingredient No. 49.1 are dissolved in a mixture consisting of 25 parts by weight of cyclohexanone,

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 in 100 000 Gewichts - teilen Wasser erhält man eine wäßrige Dispersion, die 0,02 Gew. % des Wirkstoffs enthält.65 parts by weight of a mineral oil fraction from the boiling point 210 to 280 ° C and 10 parts by weight of the adduct of 40 moles of ethylene oxide with 1 mole of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which contains 0.02% by weight of the active ingredient.

IV 20 Gewichtsteile des Wirkstoffs Nr. 49.1 werden mitIV 20 parts by weight of active ingredient No. 49.1 are with

3 Gewichtsteilen des Natriumsalzes der Diisobutylnapht alin- sulfonsäure, 17 Gewichtsteilen des Natriumsalzes einer3 parts by weight of the sodium salt of diisobutylnaphthenesulfonic acid, 17 parts by weight of the sodium salt

Ligninsulfonsäure aus einer Sulfit-Ablauge und 60 Gewichtsteilen pulverförmigen Kieselsäuregel gut vermischt und in einer Hammermühle vermählen. Durch feines Verteilen der Mischung in 20 000 Gewichtsteilen Wasser enthält man eine Spritzbrühe, die 0,1 Gew. % des Wirkstoffs enthält.Lignin sulfonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel mixed well 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. 49.1 werden mitV 3 parts by weight of active ingredient no. 49.1 are added

97 Gewichtsteilen feinteiligem Kaolin vermischt. Man erhält auf diese Weise ein Stäubemittel, das 3 Gew. % des Wirk- Stoffs enthält.97 parts by weight of finely divided kaolin mixed. In this way a dust is obtained which contains 3% by weight of the active ingredient.

VI 20 Gewichtsteile des Wirkstoffs Nr. 49.1 werden mitVI 20 parts by weight of active ingredient No. 49.1 are with

2 Gewichtsteilen Calciumsalz der Dodecylbenzolsulfonsäure, 8 Gewichtsteilen Fettalkohol-polyglykolether, 2 Gewichts- teilen Natriumsalz eines Phenol-Harnstoff-Formaldehyd-Kondensates und 68 Gewichtsteilen eines paraffinischen Mineralöls innig vermischt. Man erhält eine stabile ölige Dispersion.2 parts by weight of calcium salt of dodecylbenzenesulfonic acid, 8 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 49.1 wird in einer Mischung gelöst, die aus 70 Gewichtsteilen Cyclohexanon, 20 Gewichtsteilen ethoxyliertem Isooctylphenol und 10 Gewichtsteilen ethoxyliertem Rizinusöl besteht. Man erhält ein stabiles Emulsionskonzentrat.VII 1 part by weight of compound 49.1 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 there is ethoxylated castor oil. A stable emulsion concentrate is obtained.

VIII 1 Gewichtsteil der Verbindung 49.1 wird in einer Mischung gelöst, die aus 80 Gewichπsteilen Cyclohexanon und 20VIII 1 part by weight of compound 49.1 is dissolved in a mixture consisting of 80 parts by weight of cyclohexanone and 20

Gewichtsteilen Wettol ® EM 31 (nicht ionischer Emulgator auf der Basis von ethoxyliertem Ricinusöl) . Man erhält ein stabiles Emulsionskonzentrat.Parts by weight Wettol ® EM 31 (non-ionic emulsifier based on ethoxylated castor oil). A stable emulsion concentrate is obtained.

Zur Verbreiterung des Wirkungsspektrums und zur Erzielung synergistischer Effekte können die tricyclischen Cyclohexandionderivate mit zahlreichen Vertretern anderer herbizider oder wachstumsregulierender Wirkstoffgruppen gemischt und gemeinsam ausgebracht werden. Beispielsweise kommen als Mischungspartner l, 2, 4-Thiadiazole, 1, 3, 4-Thiadiazole, Amide, Aminophosphorsäure und deren Derivate, Aminotriazole, Anilide, (Het) -Aryloxyalkansäure und deren Derivate, Benzoesäure und deren Derivate, Benzo- thiadiazinone, 2-Aroyl-l, 3-cyciohexandione, Hetaryl-Aryl-Ketone, Benzylisoxazolidinone, Meta-CF3-phenylderivate, Carbamate, Chino- lincarbonsäure und deren Derivate, Chloracetanilide, Cyclo- hexan-1, 3-dionderivate, Diazine, Dichlorpropionsäure und deren Derivate, Dihydrobenzofurane, Dihydrofuran-3-one, Dinitroaniline, Dinitrophenole, Diphenylether, Dipyridyle, Halogencarbonsäuren und deren Derivate, Harnstoffe, 3-Phenyluracile, Imidazole, Imidazolinone, N-Phenyl-3, 4 , 5, 6-tetrahydrophthalirrd.de,To broaden the spectrum of activity and to achieve synergistic effects, the tricyclic cyclohexanedione derivatives can be mixed with numerous representatives of other herbicidal or growth-regulating active compound groups and applied together. For example, the mixing partners 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, 2 -Aroyl-l, 3-cyciohexanediones, hetaryl aryl ketones, benzylisoxazolidinones, meta-CF3-phenyl derivatives, carbamates, quinoline carboxylic acids 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-tetrahydrophthalirrd.de,

Oxadiazole, Oxirane, Phenole, Aryloxy- oder Heteroaryloxyphenoxy- propionsäureester, Phenylessigsäure und deren Derivate, Phenyl - propionsäure und deren Derivate, Pyrazole, Phenylpyrazole, Pyridazine, Pyridincarbonsäure und deren Derivate, Pyrimidyl- ether, Sulfonamide, Sulfonylharnstoffe, Triazine, Triazinone, Triazolinone, Triazolcarboxamide, Uracile in Betracht.Oxadiazoles, oxiranes, phenols, aryloxy- or heteroaryloxyphenoxypropionic esters, phenylacetic acid and its derivatives, phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acids and their derivatives, pyrimidyl ethers, sulfonamides, sulfonylhiazolines, triazines Triazolcarboxamide, Uracile into consideration.

Außerdem kann es von Nutzen sein, die Verbindungen I 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.It may also be useful to apply the compounds I 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.

Die Aufwandmengen an Wirkstoff betragen je nach Bekämpfungsziel, Jahreszeit, Zielpflanzen und Wachstumsstadium 0.001 bis 3.0, vorzugsweise 0.01 bis 1.0 kg/ha aktive Substanz (a. S.)Depending on the control target, the season, the target plants and the growth stage, the active compound application rates are 0.001 to 3.0, preferably 0.01 to 1.0 kg / ha of active substance (see also)

Anwendungsbeispiele Die herbizide Wirkung der tricyclischen Cyclohexandionderivate der Formel I ließ sich durch Gewächshausversuche zeigen:Examples of use The herbicidal activity of the tricyclic cyclohexanedione derivatives of the formula I was demonstrated by greenhouse tests:

Als Kulturgefäße dienten Plastiktöpfe mit lehmigem Sand mit etwa 3,0% Humus als Substrat. Die Samen der Testpflanzen wurden nach Arten getrennt eingesät.Plastic pots with loamy sand with about 3.0% humus served as the culture vessels. The seeds of the test plants were sown separately according to species.

Bei Vorauflaufbehandlung wurden die in Wasser suspendierten oder emulgierten Wirkstoffe direkt nach Einsaat mittels fein vertei- lender Düsen aufgebracht. Die Gefäße wurden leicht beregnet, um Keimung und Wachstum zu fördern, und anschließend mit durchsichtigen Plastikhauben abgedeckt, bis die Pflanzen angewachsen waren. Diese Abdeckung bewirkt ein gleichmäßiges Keimen der Test- pflanzen, sofern dies nicht durch die Wirkstoffe beeinträchtigt wurde.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 clear plastic hoods until the plants had grown. This cover causes the test plants to germinate evenly, provided that this has not been impaired by the active ingredients.

Zum Zweck der Nachauflaufbehandlung wurden die Testpflanzen je 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 Behandlung in die Versuchsgefäße verpflanzt. Die Aufwandmenge für die Nachauflaufbehandlung betrug 0.5 bzw. 0. 25 kg/ha a. S.For the purpose of post-emergence treatment, the test plants were first grown to a height of 3 to 15 cm, depending on the growth habit, and then treated with the active ingredients suspended or emulsified in water. 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 or 0.25 kg / ha a. S.

Die Pflanzen wurden artenspezifisch bei Temperaturen von 10 - 25°C bzw. 20 - 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 at temperatures of 10 - 25 ° C or 20 - 35 ° C depending on the species. The trial period lasted 2 to 4 weeks. During this time, the plants were cared for and their response to each treatment was evaluated.

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 Wachstumsverlauf .Evaluation was carried out on a scale from 0 to 100. 100 means no emergence of the plants or complete destruction of at least the aerial parts and 0 means no damage or normal growth.

Die in den Gewächshausversuchen verwendeten Pflanzen setzten sich aus folgenden Arten zusammen:The plants used in the greenhouse experiments are composed of the following types:

Bavercode Deutscher Name Englischer NameBavercode German name English name

CHEAL Weißer Gänsefuß lambsquartersCHEAL White goose foot lambsquarters

(goosefoot)(goosefoot)

AMARE Zurückgekrümmter redroot pigweed FuchsschwanzAMARE Curved redroot pigweed foxtail

POLPE Flohknöterich ladysthumbPOLPE knotweed ladysthumb

SOLNI Schwarzer Nacht- black nightshade schatten VERSS Ehrenpreisarten speedwellSOLNI Black nightshade shadow VERSS speedwell speed awards

Bei Aufwandmengen von 0,25 bzv;. 0,5 kg/ha a.S. zeigte die Ver- bindung 49.1 im Nachauflaufverfahren eine sehr gute Wirkung gegen die unerwünschten Pflanzen weißer Gänsefuß, zurückgekrümmter Fuchsschwanz, Flohknöterich, Schwarzer Nachtschatten und Ehrenpreisarten. With application rates of 0.25 or; 0.5 kg / ha a.S. compound 49.1 showed a very good effect in the post-emergence process against the undesirable plants white goosefoot, bent back foxtail, flea knotweed, black nightshade and honorary price types.

Claims

Patentansprücheclaims 1. Tricyclische Cyclohexandionderivate der Formel I1. Tricyclic cyclohexanedione derivatives of the formula I.
Figure imgf000081_0001
Figure imgf000081_0001
 in der die Substituenten folgende Bedeutung haben:in which the substituents have the following meaning: Ri Wasserstoff, Cχ-C6-Alkyl, Cχ-C6-Haloalkyl,Ri is hydrogen, Cχ-C 6 -alkyl, Cχ-C 6 -haloalkyl, Cχ-C6 -Alkoxy, Cχ-C6 -Haloalkoxy, Cχ-C6 -Alkylthio, Cχ-C6 -Haloalkylthio, Cχ-C6 -Alkylsulfinyl, Cχ-C6-Haloalkylsulfinyl, Cχ-Cδ -Alkylsulfonyl,Cχ-C 6 -alkoxy, Cχ-C 6 -haloalkoxy, Cχ-C 6 -alkylthio, Cχ-C 6 -haloalkylthio, Cχ-C 6 -alkylsulfinyl, Cχ-C 6 -haloalkylsulfinyl, Cχ-C δ -alkylsulfonyl, Cχ-C6 -Haloalkylsulfonyl, Halogen, Cyano- oder Nitro;Cχ-C 6 haloalkylsulfonyl, halogen, cyano- or nitro; X 0 oder NR2;X 0 or NR 2 ; R2 Wasserstoff, Cχ-C6-Alkyl, Cχ-C6-Alkoxy,R 2 is hydrogen, Cχ-C 6 alkyl, Cχ-C 6 alkoxy, Cχ-C6-Haloalkyl, Cχ-Cδ -Haloalkoxy, gegebenenfalls mit Cχ-C3 -Alkyl, Halogen, Cyano, Nitro oder Cχ-C3 -Alkylsulfonyl substituiertes Phenyl oder gegebenenfalls mit Cχ-C3 -Alkyl, Halogen, Cyano oder Nitro substituiertes Phenylsulfonyl;Cχ-C 6 -haloalkyl, Cχ-C δ -haloalkoxy, optionally substituted with Cχ-C 3 alkyl, halogen, cyano, nitro or Cχ-C 3 alkylsulfonyl or optionally substituted with Cχ-C 3 alkyl, halogen, cyano or nitro substituted phenylsulfonyl; R3, R4 Wasserstoff, Cχ-C6-Alkyl, Cχ-C6-Haloalkyl,R 3 , R 4 are hydrogen, Cχ-C 6 alkyl, Cχ-C 6 haloalkyl, Cχ-C6-Alkoxy, Cχ-Ce -Haloalkoxy, Cχ-C6 -Alkylthio, Cχ-C6 -Haloalkylthio, Cχ-C6 -Alkylsulfinyl,Cχ-C 6 -alkoxy, Cχ-Ce -haloalkoxy, Cχ-C 6 -alkylthio, Cχ-C 6 -haloalkylthio, Cχ-C 6 -alkylsulfinyl, C - Cβ -Haloalkylsulfinyl, Cx-Cβ -Alkylsulfonyl, Cχ-C6 -Haloalkylsulfonyl, NR7R8, C2-C6-Alkoxy- alkyl, Cχ-Cδ -Alkoxycarbonyl, Cχ-C6-Alkylcarbonyl, Halogen, Cyano, Nitro, gegebenenfalls mit Cχ-C3-Alkyl, Halogen, Cyano oder Nitro substituiertes Phenyl;C - Cβ -haloalkylsulfinyl, Cx-Cβ -alkylsulfonyl, Cχ-C 6 -haloalkylsulfonyl, NR 7 R 8 , C 2 -C 6 -alkoxyalkyl, Cχ-C δ -alkoxycarbonyl, Cχ-C 6 -alkylcarbonyl, halogen, Cyano, nitro, optionally substituted with Cχ-C 3 alkyl, halogen, cyano or nitro; R5 Wasserstoff oder Cx -C -Alkyl;R 5 is hydrogen or Cx -C alkyl; R6 Wasserstoff, Cχ-C6 -Alkyl oder Halogen; R7 Wasserstoff oder Cx -C& -Alkyl ;R 6 is hydrogen, Cχ-C 6 alkyl or halogen; R 7 is hydrogen or Cx -C & alkyl; R8 Cχ-C6 -Alkyl oder Cχ-C6 -AlkoxyR 8 Cχ-C 6 alkyl or Cχ-C 6 alkoxy 1 0, 1 oder 2 ;1 0, 1 or 2; n 1 oder 2 ,-n 1 or 2, - R9 substituiertes (3 -Oxo-1-cyc lohexen -2 -yl) carbonyl oder substituiertes (1, 3 -Dioxo-2 -cyclohexyl) -methyl i den;R 9 substituted (3-oxo-1-cyclohexene -2 -yl) carbonyl or substituted (1, 3-dioxo-2-cyclohexyl) methyl i den; sowie landwirtschaftlich brauchbare Salze der Verbindungen I.as well as agriculturally useful salts of the compounds I. 2. Tricyclische Cyclohexandionderivate der Formel I gemäß Anspruch 1, in der R9 für den Rest Ha oder Ilb2. Tricyclic cyclohexanedione derivatives of the formula I according to claim 1, in which R 9 for the radical Ha or Ilb
Figure imgf000082_0001
Figure imgf000082_0001
 Ha ilbHa ilb steht, wobei die Variablen folgende Bedeutung haben:stands, whereby the variables have the following meaning: Rio Hydroxy, Mercapto, Halogen, ORi"7, SRi7, SORi8,R i o hydroxy, mercapto, halogen, OR i "7 , SR i7 , SOR i8 , S02Ri8, OS02R18, P(0)Rl9R °, OP(0)Rl9R °, P(S)Ri9R20, OP(S)R19R20< NR2iR22, ONRi8Ri8 oderS0 2 R i8 , OS0 2 R 18 , P (0) R l9 R °, OP (0) R l9 R °, P (S) R i9 R 20 , OP (S) R 19 R 20 <NR 2i R 22 , ONR i8 R i8 or N-gebundenes Heterocyclyl, das partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, Cχ-C4 -Alkyl, Cχ-C -Halogenalkyl, Cχ-C4-Alkoxy oder Cχ-C4- Halogenalkoxy ;N-linked heterocyclyl, which can be partially or completely halogenated and / or can carry one to three of the following radicals: nitro, cyano, Cχ-C 4 alkyl, Cχ-C haloalkyl, Cχ-C 4 alkoxy or Cχ- C 4 - haloalkoxy; Rll, Ri5 Wasserstoff, Cχ-C4-Alkyl oder Cχ-C4 -Alkoxycarbonyl ;R ll , R i5 hydrogen, Cχ-C 4 alkyl or Cχ-C 4 alkoxycarbonyl; Ri2, Ri4, i6 Wasserstoff oder Cx -C4- Alkyl;R i2 , R i4 , i6 hydrogen or Cx -C 4 alkyl; Ri3 Wasserstoff, Halogen, Hydroxy, Cχ-Cδ -Alkyl,R i3 hydrogen, halogen, hydroxy, Cχ-C δ alkyl, Cχ-C6-Halogenalkyl, Di- (Cχ-Ce- alkoxy) -methyl, (Cχ-C6 -Alkoxy) - (Cχ-C6-alkyl- thio) -methyl, Di- (Cχ-C6- alkylthio) methyl,Cχ-C 6 -haloalkyl, di- (Cχ-Ce- alkoxy) methyl, (Cχ-C6-alkoxy) - (Cχ-C6-alkylthio) methyl, di- (Cχ-C 6 - alkylthio) methyl , Cχ-C6 -Alkoxy, Cχ-Cδ -Halogenalkoxy, Cχ-C6 -Alkylthio, Cχ-C6-Halogenalkylthio, Cχ-C6-Alkyl- sulfinyl, Cχ-C6-Halogenalkylsulfinyl, Cχ-C6 -Alkylsulfonyl, Cχ-C6-Halogenalkylsulfonyl , C -C6 -Alkoxycarbonyl, Cχ-C6-Halogenalkoxycar- bonyl ,-Cχ-C 6 -alkoxy, Cχ-C δ -haloalkoxy, Cχ-C 6 -alkylthio, Cχ-C 6 -haloalkylthio, Cχ-C 6 -alkyl- sulfinyl, Cχ-C6-haloalkylsulfinyl, Cχ-C 6 -alkylsulfonyl, Cχ-C 6 -haloalkylsulfonyl, C -C 6 -alkoxycarbonyl, Cχ-C 6 -haloalkoxycarbonyl, - l,3-Dioxolan-2-yl, 1, 3 -Dioxan-2 -yl, 1,3-Oxa- thiolan-2-yl, 1,3 Oxathian-2 -yl, 1,3-Dithio- lan-2-yl oder 1, 3-Dithian-2 -yl, wobei die sechs letztgenannter- Reste durch einen bis drei Cχ-C -Alkylresce 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 -yl or 1, 3-dithian-2 -yl, where the six latter residues can be substituted by one to three Cχ-C-alkylresce; oderor Ri2 und R13 oder R13 und R16 bilden gemeinsam eine π-Bindung oder eine Cχ -Cs -Alkylkette, die einen bis drei Reste aus fol gender Gruppe tragen kann: Halogen, Cyano, Cχ -C4 -Alkyl , Cχ - C4 -Halogenalkyl oder Cχ - C -Alkoxycarbonyl , aus ;R i2 and R 13 or R 13 and R 16 together form a π bond or a Cχ -Cs alkyl chain which can carry one to three radicals from the following group: halogen, cyano, Cχ -C 4 alkyl, Cχ - C 4 haloalkyl or Cχ - C alkoxycarbonyl, from; oderor Ri2 und Ri6 bilden gemeinsam eine Cχ-C -Alkylkette, die einen bis drei Reste aus folgender Gruppe tragen kann: Halogen, Cyano, Cχ-C4-Alkyl, Cχ-C4-Halogenalkyl oder Cχ-C4-Alkoxy- carbonyl, aus;R i2 and R i6 together form a Cχ-C alkyl chain which can carry one to three radicals from the following group: halogen, cyano, Cχ-C 4 alkyl, Cχ-C 4 haloalkyl or Cχ-C 4 alkoxy- carbonyl, from; Ri3 und Ri4 bilden gemeinsam eine -0- (CH2)p-0- , -0- (CH2)p-S- , -S- (CH2)P-S- , -0-(CH )q- oder -S- (CH2) q-Kette, die durch einen bis drei Reste aus folgender Gruppe substituiert sein kann: Halogen, Cyano, Cχ-C -Alkyl, Cχ-C -Halogenalkyl oder Cχ-C -Alkoxycarbonyl;Ri 3 and R i4 together form a -0- (CH 2 ) p -0-, -0- (CH 2 ) p -S-, -S- (CH 2 ) P -S-, -0- (CH) q - or -S- (CH 2 ) q chain, which can be substituted by one to three radicals from the following group: halogen, cyano, Cχ-C alkyl, Cχ-C haloalkyl or Cχ-C alkoxycarbonyl; oderor Rl3 und Ri4 bilden gemeinsam mit dem Kohlenstoff, an dem sie gebunden sind eine Carbonylgruppe aus;Rl 3 and R i4 together with the carbon to which they are attached form a carbonyl group; Ri7 Cχ-C6-Alkyl, C3-C6 -Alkenyl, C3-C6-Halogenalkenyl,Ri 7 Cχ-C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C3-Cε-Alkinyl, C3-C6-Halogenalkinyl, C3-C6-Cyclo- alkyl, Cχ-C6 -Alkylcarbonyl, C2 -C6-Alkenyl- carbonyl, C2-C6-Alkinylcarbonyl, C3-C6-Cyclo- alkylcarbonyl , C -C6 -Alkoxycarbonyl , C3 -C6 -Alkenyloxycarbonyl , C -C6 -Alkinyloxy- carbonyl, Cχ-C6-Alkylthiocarbonyl, Cχ-Cδ -Alkylaminocarbonyl , C3 -C6 -Alkenylaminocarbonyl , C3-C6-Alkinylaminocarbonyl,C 3 -Cε alkynyl, C 3 -C6 haloalkynyl, C 3 -C6 cycloalkyl, Cχ-C 6 alkylcarbonyl, C 2 -C 6 alkenylcarbonyl, C 2 -C 6 alkynylcarbonyl, C 3 -C 6 -cycloalkylcarbonyl, C -C 6 -alkoxycarbonyl, C 3 -C 6 -alkenyloxycarbonyl, C -C 6 -alkynyloxycarbonyl, Cχ-C 6 -alkylthiocarbonyl, Cχ-C δ -alkylaminocarbonyl, C 3 -C 6- alkenylaminocarbonyl, C 3 -C 6 -alkynylaminocarbonyl, N,N-Di (Cχ-C6-alkyl) aminocarbonyl,N, N-di (Cχ-C 6 -alkyl) aminocarbonyl, N- (C3-C6 -Alkenyl) -N- (Cχ-C6-alkyl) -aminocarbonyl, N- (C3-C6- lkinyl) -N- (Cχ-Cδ- alkyl) -aminocarbonyl, N- (Cχ-C6-Alkoxy) -N- (Cχ-C6-alkyl) -aminocarbonyl, N- (C -C6- lkenyl) -N- (Cχ-Cg- alkoxy) -aminocarbonyl, N- (C3-C6 -Alkinyl) -N- (C -C6- alkoxy) -aminocarbonyl, 5 Di- (Cχ-C6- alkyl) -aminothiocarbonyl, Cχ-C6-Alko- xyimino-Cχ-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:N- (C 3 -C 6 alkenyl) -N- (Cχ-C 6 alkyl) aminocarbonyl, N- (C 3 -C 6 -alkynyl) -N- (Cχ-C δ -alkyl) -aminocarbonyl, N- (Cχ-C 6 -alkoxy) -N- (Cχ-C 6 -alkyl) -aminocarbonyl, N - (C -C 6 - lkenyl) -N- (Cχ-Cg-alkoxy) -aminocarbonyl, N- (C 3 -C 6 -alkynyl) -N- (C -C 6 - alkoxy) -aminocarbonyl, 5 di- (Cχ-C 6 -alkyl) -aminothiocarbonyl, Cχ-C 6 -alkoxyimino-Cχ-C 6 - alkyl, where the alkyl, cycloalkyl or alkoxy radicals mentioned can be partially or completely halogenated and / or one to three of the can carry the following groups: 10 Cyano, Cχ-C4 -Alkoxy, Cχ-C4 -Alkylthio,10 cyano, Cχ-C 4 alkoxy, Cχ-C 4 alkylthio, Di- (Cχ-C - alkyl) amino, Cχ-C4 -Alkylcarbonyl, Cx -C4 -Alkoxycarbonyl , Cx -C4 -Alkoxy-Cx -C -alkoxycarbonyl, Hydroxycarbonyl , Cχ-C4 -Alkylaminocarbonyl, Di- (Cχ-C -Alkyl) aminocarbonyl, Amino-Di- (Cχ-C - alkyl) amino, Cχ-C 4 -alkylcarbonyl, Cx -C 4 -alkoxycarbonyl, Cx -C 4 -alkoxy-Cx -C -alkoxycarbonyl, hydroxycarbonyl, Cχ-C 4 -alkylaminocarbonyl, di- ( Cχ-C-alkyl) aminocarbonyl, amino 15 carbonyl, Cχ-C4-Alkylcarbonyloxy oder15 carbonyl, Cχ-C 4 alkylcarbonyloxy or C3 -C6 -Cycloalkyl ;C 3 -C 6 cycloalkyl; Phenyl, Phenyl -Cχ-C6- alkyl, Phenylcarbonyl - Cx -C6 - alkyl , Phenylcarbony1 , Phenoxycarbonyl ,Phenyl, phenyl -Cχ-C 6 - alkyl, phenylcarbonyl - Cx -C 6 - alkyl, phenylcarbony1, phenoxycarbonyl, 20 Phenoxythiocarbonyl , Phenylaminocarbonyl,20 phenoxythiocarbonyl, phenylaminocarbonyl, N- (Cχ-C6-Alkyl) -N-phenylaminocarbonyl, Phenyl -C2-C6-alkenylcarbonyl, Heterocyclyl, Heterocyclyl -Cx- C6 -alkyl , Heterocyclylcarbonyl - Cx-Cß- alkyl, Heterocyclylcarbonyl, Heterocyclyl -N- (Cχ-C 6 -alkyl) -N-phenylaminocarbonyl, phenyl -C 2 -C 6 -alkenylcarbonyl, heterocyclyl, heterocyclyl -Cx- C 6 -alkyl, heterocyclylcarbonyl - Cx-C ß - alkyl, heterocyclylcarbonyl, heterocyclyl - 25 oxycarbonyl, Heterocyclyloxythiocarbonyl, Heterocyclylaminocarbonyl, N- (Cχ-C6-Alkyl) -N-hetero- cyclylaminocarbonyl oder Heterocy- clyl-Cχ-C6-alkenylcarbonyl, wobei der Phenyl - oder der Heterocyclyl -Rest der 18 letztgenannten25 oxycarbonyl, heterocyclyloxythiocarbonyl, heterocyclylaminocarbonyl, N- (Cχ-C 6 -alkyl) -N-heterocycliclaminocarbonyl or heterocyclyl-Cχ-C 6 -alkenylcarbonyl, the phenyl - or the heterocyclyl radical of the latter 18 30 Substituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, Cχ-C4-Alkyl, Cχ-C4-Halogenalkyl, Cχ-C -Alkoxy oder Cχ-C4 -Halogenalkoxy;30 substituents can be partially or completely halogenated and / or can carry one to three of the following radicals: nitro, cyano, Cχ-C 4 alkyl, Cχ-C 4 haloalkyl, Cχ-C alkoxy or Cχ-C 4 haloalkoxy ; 3535 Ri8 Cχ-C6-Alkyl, C3-C6 -Alkenyl, C3-C6 -Alkinyl oderR i8 Cχ-C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl or C3 - CQ -Cycloalkyl, wobei die vier genannten Reste partiell oder vollständig halogeniert sein können und/oder eine bis drei der folgenden GruppenC 3 -CQ cycloalkyl, where the four radicals mentioned can be partially or completely halogenated and / or one to three of the following groups 40 tragen können: Cyano, Cχ-C4 -Alkoxy,40 can wear: Cyano, Cχ-C 4 alkoxy, Cχ-C -Halogenalkoxy, Cχ-C -Alkylthio, Cx -C4 -Halogenalkylthio, Cx -C -Alkylcarbonyl , Cχ-C4 -Alkoxycarbonyl oder Cχ-C4-Halogenalkoxycar- bonyl ;Cχ-C -haloalkoxy, Cχ-C -alkylthio, Cx -C 4 -haloalkylthio, Cx-C -alkylcarbonyl, Cχ-C 4 -alkoxycarbonyl or Cχ-C 4 -haloalkoxycarbonyl; 45 Phenyl, Phenyl -Cχ-C -alkyl, Heterocyclyl oder He- terocyclyl-Cχ-C -alkyl, wobei der Phenyl- oder der Heterocyclylrest der vier letztgenannten Substituenten partiell oder vollständig haloge- niert sein kann und/oder einen bis drei der folgenden Reste tragen kann:45 Phenyl, phenyl -Cχ-C -alkyl, heterocyclyl or heterocyclyl-Cχ-C -alkyl, where the phenyl or heterocyclyl radical of the four last-mentioned substituents can be partially or completely halogenated and / or one to three of the following radicals can carry: Nitro, Cyano, Cχ-C4-Alkyl, Cχ-C4 -Halogenalkyl, Cχ-C4 -Alkoxy, C -C4 -Halogenalkoxy oder Cx -C4 -Alkoxycarbonyl ;Nitro, cyano, Cχ-C 4 alkyl, Cχ-C 4 haloalkyl, Cχ-C 4 alkoxy, C -C 4 haloalkoxy or Cx -C 4 alkoxycarbonyl; Ris>, R20 Wasserstoff, Hydroxy, Cχ-C6 -Alkyl, Cχ-C6 -Alkoxy, Cχ-C6 -Alkylthio, Phenyl, Phenyl -Cχ-C -alkyl oder Phenoxy, wobei die drei letztgenannten Substituenten partiell oder vollständig haloge- niert sein können und/oder einen bis drei der folgenden Reste tragen können: Nitro, Cyano, Cχ-C4 -Alkyl, Cχ-C4 -Halogenalkyl, Cχ-C4 -Alkoxy, Cχ-C4 -Halogenalkoxy oder Cχ-C -Alkoxycarbonyl ,-Ris>, R 20 is hydrogen, hydroxy, Cχ-C 6 alkyl, Cχ-C 6 alkoxy, Cχ-C 6 alkylthio, phenyl, phenyl -Cχ-C alkyl or phenoxy, the three latter substituents being partially or completely can be halogenated and / or can carry one to three of the following radicals: nitro, cyano, Cχ-C 4 alkyl, Cχ-C 4 haloalkyl, Cχ-C 4 alkoxy, Cχ-C 4 haloalkoxy or Cχ -C -alkoxycarbonyl, - R2i Wasserstoff, Cχ-C6-Alkyl, C3 -C6-Alkenyl,R 2i is hydrogen, Cχ-C 6 alkyl, C 3 -C 6 alkenyl, C3 -C6 -Halogenalkenyl , C3 -C6 -Alkinyl , C3 -C6 -Halogenalkinyl , C3 -Cε -Cycloalkyl , Cχ-C6 -Alkylcarbonyl, Hydroxy, Cχ-C6 -Alkoxy, C3-C6-Alkenyloxy, C3-Cδ-Alkinyloxy, Amino, Cχ-C6-Alkylamino, Di- (Cχ-C6 -alkyl) amino oderC 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, C 3 -Cε cycloalkyl, Cχ-C 6 alkylcarbonyl, hydroxy, Cχ-C 6 alkoxy, C 3 - C 6 alkenyloxy, C 3 -C δ alkynyloxy, amino, Cχ-C 6 alkylamino, di- (Cχ-C 6 alkyl) amino or Cχ-C6-Alkylcarbonylamino, wobei die genannten Alkyl-, Cycloalkyl- oder Alkoxyreste partiell oder vollständig halogeniert sein können und/ oder einen bis drei der folgenden Reste tragen können: Cyano, Cχ-C4 -Alkoxycarbonyl, Cχ-C4-Alkyl- aminocarbonyl , Di- <Cχ-C4 -alkyl ) aminocarbonyl oder C3 -C6-Cycloalkyl;Cχ-C 6 -alkylcarbonylamino, 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, Cχ-C 4 -alkoxycarbonyl, Cχ-C 4 -alkyl - aminocarbonyl, di- <Cχ-C 4 alkyl) aminocarbonyl or C 3 -C 6 cycloalkyl; Phenyl, Phenyl -Cx -C4 -alkyl, Phenylcarbonyl , Heterocyclyl, Heterocyclyl -Cχ-C -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 fol- genden Reste tragen kann:Phenyl, phenyl -Cx-C 4 -alkyl, phenylcarbonyl, heterocyclyl, heterocyclyl -Cχ-C -alkyl or heterocyclylcarbonyl, where the phenyl or heterocyclyl radical of the six latter substituents can be partially or completely halogenated and / or one to three of the can carry the following residues: Nitro, Cyano, Cχ-C4 -Alkyl, C -C4 -Halogenalkyl, Cχ-C -Alkoxy oder Cx -C4-Halogenalkoxy;Nitro, cyano, Cχ-C 4 alkyl, C -C 4 haloalkyl, Cχ-C alkoxy or Cx -C 4 haloalkoxy; R22 Wasserstoff, Cχ-C6-Alkyl, C3 -Cβ-Alkenyl oder C3-C6 -Alkinyl; p 2 , 3 oder 4 ;R 22 is hydrogen, Cχ-C 6 alkyl, C 3 -Cβ alkenyl or C 3 -C 6 alkynyl; p 2, 3 or 4; q 1 , 2 , 3 , 4 oder 5 .q 1, 2, 3, 4 or 5. 3. Tricyclische Cyclohexandionderivate der Formel III gemäß Anspruch 13. tricyclic cyclohexanedione derivatives of the formula III according to claim 1
Figure imgf000086_0001
Figure imgf000086_0001
 in der die Substituenten die in Anspruch 1 angegebenen Bedeutungen haben.in which the substituents have the meanings given in claim 1. 4. Tricyclische Cyclohexandionderivate der Formel III nach Anspruch 3, in der der Substituent R9 die in Anspruch 1 angegebene Bedeutung hat und die übrigen Substituenten die folgende Bedeutung haben:4. Tricyclic cyclohexanedione derivatives of the formula III according to claim 3, in which the substituent R 9 has the meaning given in claim 1 and the other substituents have the following meaning: Ri Wasserstoff, Cχ-C6-Alkyl, Cχ-C6-Haloalkyl,R i is hydrogen, Cχ-C 6 alkyl, Cχ-C 6 haloalkyl, Cχ-C6-Alkoxy, Cχ-C6 -Alkylthio, Cχ-C6 -Alkylsulfonyl, Halogen, Cyano- oder Nitro,-Cχ-C 6 -alkoxy, Cχ-C 6 -alkylthio, Cχ-C 6 -alkylsulfonyl, halogen, cyano- or nitro, - R3, R4 Wasserstoff, Cχ-C6-Alkyl, Cχ-C6 -Alkoxy, Cχ-C6 -Alkylthio, Cχ-C6 -Alkylsulfonyl,R 3 , R 4 are hydrogen, Cχ-C 6 -alkyl, Cχ-C 6 -alkoxy, Cχ-C 6 -alkylthio, Cχ-C 6 -alkylsulfonyl, C - Cζ -Alkoxyalkyl, 0χ -C6-Alkoxycarbonyl , Cχ-C6-Alkylcarbonyl, Halogen, gegebenenfalls mit Cχ-C3 -Alkyl, Halogen, Cyano oder Nitro substituiertes Phenyl;C - Cζ alkoxyalkyl, 0χ -C 6 alkoxycarbonyl, Cχ-C 6 alkylcarbonyl, halogen, optionally substituted with Cχ-C 3 alkyl, halogen, cyano or nitro; R5 Wasserstoff;R 5 is hydrogen; R6 Wasserstoff, Cχ-C3-Alkyl oder Halogen;R 6 is hydrogen, Cχ-C 3 alkyl or halogen; n 1 oder 2. Tricyclische Cyclohexandionderivate der Formel IV gemäß Anspruch 1n 1 or 2. Tricyclic cyclohexanedione derivatives of the formula IV according to Claim 1
Figure imgf000087_0001
Figure imgf000087_0001
 in der die Substituenten die in Anspruch 1 angegebenen Bedeutungen haben.in which the substituents have the meanings given in claim 1. Tricyclische Cyclohexandionderivate der Formel IV nach Anspruch 5, in der der Substituent R9 die in Anspruch 1 angegebene Bedeutung hat und die übrigen Substituenten die folgende Bedeutung haben:Tricyclic cyclohexanedione derivatives of the formula IV according to Claim 5, in which the substituent R 9 has the meaning given in Claim 1 and the other substituents have the following meaning: R1 Wasserstoff, Cχ-C6 -Alkyl, Cχ-C6-Haloalkyl,R 1 is hydrogen, Cχ-C 6 alkyl, Cχ-C 6 haloalkyl, Cχ-C6-Alkoxy, Cχ-C6-Alkylthio, Cχ-C6-Alkyl- sulfonyl, Halogen, Cyano oder Nitro;Cχ-C 6 alkoxy, Cχ-C 6 alkylthio, Cχ-C 6 alkyl sulfonyl, halogen, cyano or nitro; R2 Wasserstoff, Cχ-Cδ-Alkyl, Cχ-C6 -Alkoxy,R 2 is hydrogen, Cχ-C δ alkyl, Cχ-C 6 alkoxy, Cχ-Cδ-Haloalkyl, Cχ-C6 -Haloalkoxy, gegebenenfalls mit Cχ-C3-Alkyl, Halogen, Cyano, Nitro oder Cχ-C3 -Alkylsulfonyl substituiertes Phenyl oder gegebenenfalls mit Cχ-C3 -Alkyl, Halogen, Cyano oder Nitro substituiertes Phenylsulfonyl;Cχ-C δ- haloalkyl, Cχ-C 6 -haloalkoxy, optionally substituted with Cχ-C 3 alkyl, halogen, cyano, nitro or Cχ-C 3 alkylsulfonyl or optionally substituted with Cχ-C 3 alkyl, halogen, cyano or nitro substituted phenylsulfonyl; R3, R4 Wasserstoff, Cχ-C6 -Alkyl, Cχ-C6 -Alkoxy, Cχ-C6 -Alkylthio, Cχ-C6 -Alkylsulfonyl, C2 -Cδ -Alkoxyalkyl, Cx -C6-Alkoxycarbonyl , Cχ-C6-Alkylcarbonyl, Halogen, gegebenenfalls mitR 3 , R 4 are hydrogen, Cχ-C 6 -alkyl, Cχ-C 6 -alkoxy, Cχ-C 6 -alkylthio, Cχ-C 6 -alkylsulfonyl, C 2 -C δ -alkoxyalkyl, Cx -C 6 -alkoxycarbonyl, Cχ-C 6 alkylcarbonyl, halogen, optionally with Cχ-C3 -Alkyl, Halogen, Cyano oder Nitro substituiertes Phenyl;Cχ-C 3 alkyl, halogen, cyano or nitro substituted phenyl; R5 Wasserstoff ;R 5 is hydrogen; R6 Wasserstoff, Cχ-C3 -Alkyl oder Halogen;R 6 is hydrogen, Cχ-C 3 alkyl or halogen; n 1 oder 2. n 1 or 2. . Tricyclische Carbonsäurederivate der Formel V. Tricyclic carboxylic acid derivatives of the formula V
Figure imgf000088_0001
Figure imgf000088_0001
 in der T die folgende Bedeutung hat:where T has the following meaning: T Halogen, OH oder Cχ-C4 -AlkoxyT halogen, OH or Cχ-C 4 alkoxy und die übrigen Substituenten die in Anspruch 1 angegebene Bedeutung haben.and the other substituents have the meaning given in claim 1. 8. Tricyclische Carbonsäurederivate der Formel VI gemäß An- spruch 78. Tricyclic carboxylic acid derivatives of the formula VI according to claim 7
Figure imgf000088_0002
Figure imgf000088_0002
 in der T die folgende Bedeutung hat:where T has the following meaning: T Halogen, OH oder Cχ-C4 -AlkoxyT halogen, OH or Cχ-C 4 alkoxy und die übrigen Substituenten die in Anspruch 1 angegebene Bedeutung haben. and the other substituents have the meaning given in claim 1. 9. Tricyclische Carbonsäurederivate der Formel VII gemäß Anspruch 79. tricyclic carboxylic acid derivatives of the formula VII according to claim 7
Figure imgf000089_0001
Figure imgf000089_0001
 in der T die folgende Bedeutung hat:where T has the following meaning: 15 Halogen, OH oder Cχ-C4 -Alkoxy15 halogen, OH or Cχ-C 4 alkoxy und die übrigen Substituenten die in Anspruch 1 angegebene Bedeutung haben.and the other substituents have the meaning given in claim 1. 20 10. Verfahren zur Herstellung der tricyclischen Carbonsäurederivate VI gemäß Anspruch 8, dadurch gekennzeichnet, daß man die Verbindungen der Formel VIII in Gegenwart eines Oxida- tionsmittels zu den Verbindungen der Formel IX cyclisiert und anschließend oxidiert,10. A process for the preparation of the tricyclic carboxylic acid derivatives VI as claimed in claim 8, characterized in that the compounds of the formula VIII are cyclized in the presence of an oxidizing agent to give the compounds of the formula IX and then oxidized, 2525 :
Figure imgf000089_0002
:
Figure imgf000089_0002
 VIII IXVIII IX 3535 40 Oxidationsmittel40 oxidizing agents
Figure imgf000089_0003
Figure imgf000089_0003
 VIVI 45 wobei T Cχ-C -Alkoxy bedeutet45 where T is Cχ-C alkoxy und die übrigen Substituenten die in Anspruch 1 angegebene Bedeutung haben.and the other substituents have the meaning given in claim 1. 11. Verfahren zur Herstellung der tricyclischen Carbonsäurederivate VII gemäß Anspruch 9, dadurch gekennzeichnet, daß man die Verbindungen der Formel X in Gegenwart eines Oxidati- onsmittels zu den Verbindungen der Formel XI cyclisiert und anschließend oxidiert,11. A process for the preparation of the tricyclic carboxylic acid derivatives VII according to claim 9, characterized in that the compounds of the formula X are cyclized in the presence of an oxidizing agent to give the compounds of the formula XI and then oxidized,
Figure imgf000090_0001
Figure imgf000090_0001
 XIXI OxidationsmittelOxidizing agent
Figure imgf000090_0002
Figure imgf000090_0002
 VIIVII wobei T Cχ-C -Alkoxy bedeutetwhere T is Cχ-C alkoxy und die übrigen Substituenten die in Anspruch 1 angegebene Bedeutung haben.and the other substituents have the meaning given in claim 1. 12. Verfahren zur Herstellung von Verbindungen der Formel I mit R10=Hydroxy gemäß Anspruch 2, dadurch gekennzeichnet, daß man ein Cyclohexan-l,3-dion XII mit einer aktiven Carbonsäure Va oder einer Carbonsäure Vb,
Figure imgf000091_0001
12. A process for the preparation of compounds of formula I with R 10 = hydroxy according to claim 2, characterized in that a cyclohexane-1,3-dione XII with an active carboxylic acid Va or a carboxylic acid Vb,
Figure imgf000091_0001
 XII oderXII or
Figure imgf000091_0002
Figure imgf000091_0002
Figure imgf000091_0003
Figure imgf000091_0003
Figure imgf000091_0004
Figure imgf000091_0004
 I (mit Ri° = OH) wobei die Variablen R1 bis Ri6, X, 1 und n die unter Anspruch 1 genannte Bedeutung haben und L1 für eine nucleophil verdrängbare Abgangsgruppe steht, acyliert und das Acylierungsprodukt in Gegenwart eines Katalysators zu den Verbindungen I mit Ri° = Hydroxy umlagert. I (with Ri ° = OH), where the variables R 1 to R i6 , X, 1 and n have the meaning given in claim 1 and L 1 represents a nucleophilically displaceable leaving group, acylated and the acylation product in the presence of a catalyst to give the compounds I rearranged with R i ° = hydroxy. 13. Herbizides Mittel, enthaltend mindestens ein tricyclisches13. Herbicidal agent containing at least one tricyclic Cyclohexandionderivat der Formel I gemäß Anspruch 1 und übliche inerte Zusatzstoffe.Cyclohexanedione derivative of the formula I according to Claim 1 and customary inert additives. 14. Verfahren zur Bekämpfung unerwünschten Pflanzenwuchses, dadurch gekennzeichnet, daß man eine herbizid wirksame Menge eines tricyclischen Cyclohexandionderivates der Formel I gemäß Anspruch 1 auf die Pflanzen oder deren Lebensraum einwirken läßt. 14. A method for controlling undesirable plant growth, characterized in that a herbicidally effective amount of a tricyclic cyclohexanedione derivative of the formula I according to claim 1 is allowed to act on the plants or their habitat.
PCT/EP2000/002565 1999-04-01 2000-03-23 Tricyclic cyclohexanedione derivatives Ceased WO2000059911A2 (en)

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