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EP1084116A1 - Cyclohexenondioxothio chromanoyl derivatives - Google Patents

Cyclohexenondioxothio chromanoyl derivatives

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Publication number
EP1084116A1
EP1084116A1 EP99923435A EP99923435A EP1084116A1 EP 1084116 A1 EP1084116 A1 EP 1084116A1 EP 99923435 A EP99923435 A EP 99923435A EP 99923435 A EP99923435 A EP 99923435A EP 1084116 A1 EP1084116 A1 EP 1084116A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
alkoxy
radicals
methyl
aminocarbonyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP99923435A
Other languages
German (de)
French (fr)
Inventor
Matthias Witschel
Klaus Langemann
Wolfgang Von Deyn
Ulf Misslitz
Ernst Baumann
Stefan Engel
Guido Mayer
Ulf Neidlein
Oliver Wagner
Roland Götz
Martina Otten
Karl-Otto Westphalen
Helmut Walter
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
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Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Publication of EP1084116A1 publication Critical patent/EP1084116A1/en
Withdrawn legal-status Critical Current

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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
    • C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
    • A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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    • A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
    • A01N43/18—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with sulfur as the ring hetero atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • A—HUMAN NECESSITIES
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    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
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    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
    • C07D339/08—Six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/08—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing alicyclic rings

Definitions

  • the present invention relates to new cyclohexenone dioxothio-chromanoyl derivatives of the formula I,
  • R 1 is hydrogen, nitro, halogen, cyano, -CC 6 alkyl
  • Ci-C ß -haloalkyl Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, C ⁇ -C 6 alkylthio, C ⁇ -C 6 -haloalkylthio, C ⁇ -C 6 alkylsulfinyl, Ci-C ⁇ -haloalkylsulfinyl, Ci -C ⁇ alkyl sulfonyl, -C-C 6 haloalkylsulfonyl, aminosulfonyl, N- (Ci-Ce-alkyl) -aminosulfonyl, N, N-di- (C ⁇ -C 6 alkyl) - aminosulfonyl, N- (Ci -Cg-alkylsulfonyl) -amino, N- (Ci-Cg-haloalkylsulfonyl) -amino, N- (Ci-Cg-alkyl) -
  • R 2 Ci-Cg-alkyl, -CC 6 -haloalkyl, C ⁇ -Cg-alkoxy or Ci-C ⁇ -haloalkoxy;
  • R 3 is hydrogen, Ci-Cg-alkyl or halogen
  • R 4 , R 5 are hydrogen, nitro, halogen, cyano, C ⁇ -Cg-alkyl,
  • Ci-C ß -haloalkyl Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, C ⁇ -C 6 -alkylthio, C ⁇ -C 6 -haloalkylthio, Ci-Cg-alkylsulfinyl, C ⁇ -Cg-haloalkylsulfinyl, C] _ -Cg-alkyl-sulfonyl, Ci-Cg-haloalkylsulfonyl, N-Ci-Cg-alkylamino, N-Ci-Cg-haloalkylamino, N, N-Di - (Ci-Cg -alkyl) amino, N-Ci- Cg-alkoxyamino, N- (Ci -Cg-alkoxy) -N- (-C-C 6 - alkyl) amino, 1-tetrahydropyrrolyl, 1-piperidinyl, 4-morpholinyl or 1-
  • R 4 and R 5 together form a -0- (CH 2 ) m -0-, -O- (CH 2 ) m -S -,
  • R 4 and R 5 together form a - (CH 2 ) p chain, which can be interrupted by oxygen or sulfur and / or can be substituted by one to four radicals from the following group:
  • R 4 and R 5 together form a methylidene group, which can be substituted by one or two radicals from the following group:
  • Halogen hydroxy, formyl, cyano, C ⁇ -Cg-alkyl, C ⁇ -C 6 -haloalkyl, C ⁇ -C 5 -alkoxy, Ci-Cg-haloalkoxy, Ci-Cg-alkylthio, Ci-Cg-haloalkylthio, Ci-Cg- Alkylsulfinyl, Ci-Cg-haloalkylsulfinyl, Ci-Cg-alkylsulfonyl or Ci-Cg-haloalkylsulfonyl;
  • R 7 is a compound Ha or Ilb
  • R 9 nitro, halogen, cyano, Ci-Cg-alkyl, C ⁇ -C 6 -haloalkyl, di- (Ci-Cg-alkoxy) -methyl, di- (Ci-Cg-alkylthio) -methyl, (Ci-C - Alkoxy) (Ci-Cg-alkylthio) methyl, hydroxy, Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, C -Cg-alkylthio, Ci-Cg-haloalkylthio, Ci-Cg-alkylsulfinyl, Ci-Cg-
  • Haloalkylsulfinyl Ci-Cg-alkylsulfonyl, Ci-Cg-haloalkylsulfonyl, Ci-Cg-alkylcarbonyl, Ci-Cg-haloalkylcarbonyl, Ci-Cg-alkoxycarbonyl or Ci-Cg-haloalkoxycarbonyl;
  • R 9 which are bonded to the same carbon, together form a -0- (CH 2 ) m -0-, -0- (CH 2 ) m -S-, -S- (CH 2 ) m -S- or -0- (CH) n chain, which can be substituted by one to three radicals from the following group: halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C -C 4 alkoxycarbonyl ;
  • R 9 radicals which are bonded to the same carbon together form a - (CH 2 ) p chain which can be interrupted by oxygen or sulfur and / or can be substituted by one to four radicals from the following group:
  • R 9 radicals which are bonded to the same carbon together form a methylidene group which can be substituted by one or two radicals from the following group: halogen, hydroxy, formyl, cyano, Ci-Cg-alkyl,
  • Ci-Cg-haloalkyl Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, Ci-Cg-alkylthio, Ci-Cg-haloalkylthio, Ci-Cg-alkyl- sulfinyl, Ci-Cg-haloalkylsulfinyl, Ci-Cg-alkylsulfonyl, Ci-Cg-haloalkylsulfonyl;
  • R 9 radicals which are bonded to different carbons together form a - (CH 2 ) n ⁇ chain, which can be substituted by one to three radicals from the following group:
  • Phenylaminocarbonyl N- (Ci-Cg-Alkyl) -N- (phenyl) -aminocarbonyl, Heterocyclylaminocarbonyl, N- (Ci-Cg-Alkyl) - N- (heterocyclyl) -aminocarbonyl, Phenyl-C -C 6 -alkenyl - carbonyl or heterocyclyl-C 2 -Cg-alkenylcarbonyl, where the phenyl and heterocyclyl radicals of the last 18 substituents can be partially or completely halogenated and / or can carry one to three of the following radicals: nitro, cyano, C 1 -C 4 - Alkyl, -CC 4 -haloalkyl, -C-C 4 ⁇ alkoxy or -C-C 4 ⁇ haloalkoxy;
  • R 11 , R 12 Ci-Cg-alkyl, C 3 -Cg-alkenyl, C 3 -Cg-haloalkenyl,
  • Di- (Ci-Cg-haloalkyl) amino where the alkyl, cycloalkyl and alkoxy radicals mentioned can be partially or completely halogenated and / or can carry one to three of the following groups: cyano, C 1 -C 4 -alkoxy, C ⁇ - C 4 -Alkylthio, di- (-C 4 -alkyl) - amino, -C-C 4 -alkylcarbonyl, C ⁇ -C 4 -alkoxycarbonyl, C ⁇ -C 4 -alkoxy-C ⁇ -C 4 -alkoxycarbonyl, di- (C ⁇ ⁇ C 4 -alkyl) -ami - no -C-C 4 alkoxycarbonyl, hydroxycarbonyl, -C-C 4 ⁇ alkyl-aminocarbonyl, di- (C -C 4 -alkyl) -aminocarbonyl, aminocarbonyl, C ⁇ -C 4 -Al
  • R 13 Ci - Cg alkyl, C 3 - Cg alkenyl, C 3 - Cg - haloalkenyl,
  • Ci-Cg alkyl C 3 -Cg alkenyl, C 3 -C 6 alkynyl or Ci-Cg alkylcarbonyl;
  • the invention also relates to processes for the preparation of compounds of the formula I, compositions which contain them and the use of these derivatives or compositions containing them for controlling harmful plants.
  • herbicidal compositions which contain the compounds I and have a very good herbicidal action. Processes for the preparation of these agents and processes for Control of undesired plant growth with the compounds I found.
  • the compounds of the formula I can contain one or more chiral centers and are then present as enantiomers or diastereomer mixtures.
  • 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. In general, the salts of those cations or the acid addition salts of those acids whose cations or anions do not adversely affect the herbicidal activity of the compounds I
  • the cations used are, in particular, ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium and magnesium, and of the transition metals, preferably manganese, copper, zinc and iron, and ammonium, where if desired one to four hydrogen atoms by C ⁇ - C 4 alkyl, hydroxy -CC 4 alkyl, Ci-C 4 alkoxy-C 1 -C 4 alkyl, hydroxy-Ci-C 4 alkoxy-C 1 -C 4 alkyl, phenyl or Benzyl can be replaced, preferably ammonium, dimethylammonium, diisopropylammonium, tetramethylammonium, tetrabutylammonium, 2 - (2-hydroxyeth-1-oxy) eth-1-ylammonium, di (2-hydroxyeth-l-yl) ammonium, trimethyl - Benzylammonium, 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 1 -C 4 -alkanoic acids, preferably formate, acylate , Propionate and butyrate.
  • C 1 -C 4 alkyl for example methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl or 1, 1-dimethylethyl;
  • Ci-Cg-alkyl as well as the alkyl parts of -C-Cg-alkoxyimino-C ⁇ -Cg-alkyl, N- (Ci-Cg-alkylamino) -imino-Ci-Cg-alkyl, N- (di-Ci-Cg- alkylamino) imino-Ci-Cg-alkyl, N (Ci-Cg-alkoxy) -N- (Ci-Cg-alkyl) aminocarbonyl, N- (C 3 -Cg-alkenyl) -N- (Ci-Cg- alkyl) -aminocarbonyl, (C 3 -Cg-alkynyl) -N- (Ci-Cg-alkyl) -aminocarbonyl, N- (Ci-Cg-alkyl) -N-phenylaminocarbonyl, N- (Ci-Cg-alkyl) -
  • C ⁇ ⁇ C 4 -haloalkyl a C ⁇ -C4 alkyl group such as overall Nannt above which is partially or fully substituted by fluorine, chlorine, bromine and / or iodine, eg chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, Trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorofluoromethyl, 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,
  • Ci-Cg-haloalkyl, and the haloalkyl parts of NC -Cg-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 eg methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1, 1-dimethylethoxy;
  • Ci-Cg-haloalkoxy C ⁇ -C4-haloalkoxy, as mentioned above, and e.g. 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy;
  • C 1 -C 4 -Alkylthio for example methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio or 1, 1-dimethylethylthio;
  • Ci-Cg-alkylthio and the alkylthio parts of Ci-Cg-alkylthio-carbonyl, di- (-C-Cg-alkylthio) methyl and
  • C ⁇ -C4 ⁇ haloalkylthio a C ⁇ -C4-alkylthio, as mentioned above, which is partially or fully substituted by fluorine, chlorine, bromine and / or iodine, eg fluorine - methylthio, difluoromethylthio, trifluoromethylthio, difluoromethylthio chlorine, 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-chloro-2, 2-di-fluoroethylthio, 2, 2-dichloro-2-fluoroethylthio, pentafluoro
  • Ci-Cg-haloalkylthio -C-C 4 -haloalkylthio, as mentioned above, and, for example, 5-fluoropentylthio, 5-chloropentylthio, 5-bromotylthio, 5-iodopentylthio, undecafluoropentylthio, 6-fluorhexylthio, 6-chlorohexylthio, 6-bromohexylthio, 6-iodohexylthio or dodecafluorohexylthio;
  • Ci-Cg-haloalkylsulfinyl a Ci-Cg-alkylsulfinyl radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example fluoromethylsulfinyl, difluoromethylsulfinyl, trifluoromethylsulfinyl, chlorodifluoromethylsulfinyl, bromodifluoromethylsulfonyl 2-fluoroethylsulfinyl, 2-chloroethylsulfinyl, 2-bromoethylsulfinyl, 2-iodoethylsulfinyl, 2, 2-difluoroethylsulfinyl, 2,2, 2-trifluoroethylsulfinyl, 2,2, 2-trichloroethylsulfinyl, 2-chloro-2-fluoroe
  • Ci-Cg-haloalkylsulfonyl and the haloalkyl radicals of N- (Ci-Cg-haloalkylsulfonyl) amino and N- (Ci-Cg-alkyl) -N- (Ci-Cg-haloalkylsulfonyl) amino: a Ci-Cg-alkylsulfonyl -
  • the rest as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example fluoromethylsulfonyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, 2-fluoroethylsulfonyl, 2-chloroethyl-sulfonyl, 2-chloroethylsulfonyl 2-io
  • Ci-Cg-alkylamino and the alkylamino residues of N- (C ⁇ ⁇ Cg-
  • Alkylamino -imino-Ci-Cg-alkyl, e.g. Methylamino, ethylamino, propylamino, 1-methylethylamino, butylamino, 1-methylpropylamino, 2-methylpropylamino, 1, 1-dimethylethylamino, pentylamino, 1-methylbutylamino, 2-methylbutylamino, 3-methylbutylamino, 2, 2-dimethylpropylamino 1-ethylpropylamino, hexylamino, 1, 1-dimethylpropylamino, 1, 2-dimethylpropylamino, 1-methylpentylamino, 2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino, 1, 1-dimethylbutylamino, 1, 2- Dimethylbutylamino, 1, 3-dimethylbutylamino, 2, 2-dimethylbutylamino, 2, 3-d
  • C 1 -C 4 -alkylamino) sulfonyl for example methylaminosulfonyl, ethylaminosulfonyl, propylaminosulfonyl, 1-methylethylaminosulfonyl, butylaminosulfonyl, 1-methylpropylaminosulfonyl, 2-methylpropylaminosulfonyl or 1, 1-dirnethylethylamino sulfonyl
  • (Ci-Cg-alkylamino) sulfonyl (C 1 -C 4 -alkylanu.no) sulfonyl, as mentioned above, and for example pentylaminosulfonyl, 1-methylbutylaminosulfonyl, 2-methylbutylaminosulfonyl, 3-methylbutylaminosulfonyl, 2, 2- Dimethylpropylaminosulfonyl, 1-ethylpropylaminosulfonyl, hexylaminosulfonyl, 1, 1-dimethylpropylaminosulfonyl, 1, 2-dimethylpropylaminosulfonyl, 1-methylpentylaminosulfonyl, 2-methylpentylaminosulfonyl, 3-methylpentyl, 1-methylpentyl, 1-methylpentyl, 4-methyl-4-nylsulfonyl butylaminosulfonyl, 1, 2-
  • Di- (Ci-Cg-alkyl) -aminosulfonyl Di- (-C-C 4 ⁇ alkyl) -aminosulfonyl, as mentioned above, and for example N-methyl-N-pentylaminosulfonyl, N-methyl-N- (1- methylbutyl) -aminosulfonyl, N-methyl-N- (2-methylbutyl) -aminosulfonyl, N-methyl-N- (3-methylbutyl) -aminosulfonyl, N-methyl-N- (2,2-dimethylpropyl) -aminosulfonyl, N -Methyl-N- (1-ethyl-propyl) -aminosulfonyl, N-methyl-N-hexylaminosulfonyl, N-methyl-N- (1, 1-dimethylpropyl) -aminosulfonyl, N-methyl- N- N- (1, 2- di
  • N- (1-methylethyl) -N- (2-methylpropyl) amino N- (1, 1-dimethylethyl) -N- (1-methylethyl) amino, N-butyl-N- (1-methylpropyl) - amino, N-butyl-N- (2-methylpropyl) amino, N-butyl-N- (1, 1-dimethylethyl) amino, N- (1-methylpropyl) -N- (2-methylpropyl) amino, N- (1, 1-dimethylethyl) -N- (1-methylpropyl) amino or N- (1, 1-dimethylethyl) -N- (2-methylpropyl) amino;
  • C 1 -C 4 -alkylcarbonyl for example methylcarbonyl, ethylcarbonyl, propylcarbonyl, 1-methylethylcarbonyl, butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl or 1, 1-dimethylethylcarbonyl;
  • Ci-Cg-alkylcarbonyl and the alkylcarbonyl radicals of
  • C 1 -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 -Dimethylpropylcarbonyl, 1-methylpentylcarbonyl, 2-methylpentylcarbonyl, 3-methylpentylcarbonyl, 4-methylpentylcarbonyl, 1, 1-dimethylbutylcarbonyl, 1, 2-dimethylbutylcarbonyl, 1, 3-dimethylbutylcarbonyl, 2, 2, -dimethylbutyl - carbonyl, 2, 3-dimethylbutylcarbonyl, 3, 3-dimethylbutylcarbonyl, 1-ethylbutylcarbonyl, 2-ethylbutylcarbonyl
  • C 1 -C 2 -alkylcarbonyl C 1 -C 6 -alkylcarbonyl, as mentioned above, and heptylcarbonyl, octylcarbonyl, pentadecylcarbonyl or heptadecylcarbonyl;
  • Ci-Cg-haloalkylcarbonyl a Ci-Cg-alkylcarbonyl radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, e.g. Chloroacetyl, dichloroacetyl, trichloroacetyl, fluoroacetyl,
  • alkoxycarbonyl parts of di- (C 4 -C 4 alkyl) amino-C 4 -C 4 alkoxycarbonyl, for example methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, 1-methylethoxycarbonyl, butoxycarbonyl, 1- Methylpropoxycarbonyl, 2-methylpropoxycarbonyl or 1, 1-dimethylethyloxycarbonyl;
  • (Ci-Cg-alkoxy) carbonyl (-C-C 4 alkoxy) carbonyl, as mentioned above, and for example pentoxycarbonyl, 1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 2, 2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl , Hexoxycarbonyl, 1, 1-dimethylpropoxycarbonyl, 1, 2-dimethylpropoxycarbonyl,
  • Ci-Cg-haloalkoxycarbonyl a -CC 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, bromodifluoro- methoxycarbonyl, 2-fluoroethoxycarbonyl, 2-chloroethoxycarbonyl, 2-bromoethoxycarbonyl, 2-iodoethoxycarbonyl, 2,2-di-fluoroethoxycarbonyl, 2, 2, 2-trifluoroethoxycarbonyl, 2-chloro-2-fluoroethoxycarbonyl, 2-chloro-2, 2-difluoroethoxycarbonyl, 2, 2-dichloro-2-fluoroethoxycarbonyl, 2,2, 2-trichloroethoxy
  • (-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, ethyl - aminocarbonyl, propylaminocarbonyl, 1-methylethylaminocarbonyl, butylaminocarbonyl, 1-methylpropylaminocarbonyl, 2-methylpropylaminocarbonyl or 1, 1-dimethylethylaminocarbonyl;
  • (Ci-Cg-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-dirnethylpropyl - aminocarbonyl, 1, 2-dimethylpropylaminocarbonyl, 1-methylpentylaminocarbonyl, 2-methylpentylaminocarbonyl, 3-methylpentylaminocarbonyl, 4-methylpentylaminocarbonyl, 1,1-diyl , 2-Dimethylbutylaminocarbonyl, 1, 3-Dimethylbutylaminocarbonyl, 2, 2-Dirnethylb tylamin
  • Di- (-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, -Di- (1-methylpropyl) -aminocarbonyl, N, N-di- (2-methylpropyl) -aminocarbonyl, N, N-di- (1, 1-dimethylethyl) -aminocarbo- nyl, N-ethyl-N-methylaminocarbonyl, N-methyl-N-propylamino-carbonyl, N-methyl-N- (1-methylethyl) -aminocarbonyl, N-butyl-N-methylaminocarbonyl, N-methyl
  • Di- (Ci-Cg-alkyl) -aminocarbonyl Di- (-C-C 4 -alkyl) -aminocarbonyl, as mentioned above, as well as, for example, N-methyl-N-pentylaminocarbonyl, N-methyl-N- (1-methylbutyl) -aminocarbonyl, N-methyl-N- (2-methylbutyl) -aminocarbonyl, N-methyl-N- (3-methylbutyl) -aminocarbonyl, N-methyl-N- (2, 2-dimethylpropyl) -aminocarbonyl, N-methyl -N- (1-ethyl-propyl) -aminocarbonyl, N-methyl-N-hexylaminocarbonyl, N-methyl-N- (1, 1-dimethylpropyl) -aminocarbonyl, N-methyl-N- (1,2-dimethylpropyl) aminocarbonyl, N-methyl
  • 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-trimethylpropyl) aminocarbonyl, N-methyl- N- N-methyl
  • Di- (Ci-Cg-alkyl) -aminothiocarbonyl e.g. N, -dimethylamino-thiocarbonyl, N, N-diethylaminothiocarbonyl, N, N-di- (1-methyl-ethyl) aminothiocarbonyl, N, N-dipropylaminothiocarbonyl,
  • N, N-dibutylaminothiocarbonyl N, N-di- (1-methylpropyl) aminothiocarbonyl, N, N-di- (2-methylpropyl) aminothiocarbonyl, N, N-di- (1, 1-dimethylethyl) aminothiocarbonyl, N-ethyl-N-methylaminothiocarbonyl, N-methyl-N-propylaminothiocarbonyl, N-methyl-N- (1-methylethyl) aminothiocarbonyl, N-butyl-N-methylaminothiocarbonyl, N-methyl-N- (1-methyl - propyl) -aminothiocarbonyl, N-methyl-N- (2-methylpropyl) -aminothiocarbonyl, N- (1, 1-dimethylethyl) -N-methylaminothio-carbonyl, N-ethyl-N-propylaminothiocarbony
  • 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) aminothiocarbonyl, N-methyl-N- (1-ethyl-2-methylpropyl) aminothiocarbonyl, N-ethyl-N-pentylaminothiocarbonyl, N- Ethyl-N- (1-methylbutyl) amino hiocarbonyl, N-ethyl-N- (2-methylbutyl) aminothiocarbonyl, N-ethyl-N- (3-methylbutyl) aminothiocarbonyl, N-ethyl-N- (2, 2-dimethyl-propyl) -aminothiocarbonyl, N-e
  • C 1 -C 4 -alkoxy-C 4 -alkoxy C 1 -C 4 -alkoxy, and the alkoxyalkoxy parts of C 1 -C 4 -alkoxy-C 4 -C 4 -alkoxycarbonyl: C 1 -C 4 -alkoxy, as mentioned above, substituted -CC 4 - Alkoxy, e.g.
  • C 3 -Cg alkenyl and the alkenyl parts of C 3 -Cg alkenylcarbonyl, C 3 -Cg alkenyloxy, C -Cg alkenyloxycarbonyl, C 3 -Cg alkenylaminocarbonyl, N- (C -Cg alkenyl) - N- (Ci-Cg) alkyl-aminocarbonyl, N- (C 3 -Cg-alkenyl) -N- (Ci-Cg-alkoxy) aminocarbonyl: e.g.
  • C 2 -Cg alkenyl and the alkenyl parts of C 2 -Cg alkenylcarbonyl, phenyl-C -Cg alkenylcarbonyl and heterocyclyl-C -Cg alkenylcarbonyl: C 3 -Cg alkenyl, as mentioned above, and ethenyl;
  • C -Cg haloalkenyl a C -Cg 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-dichloroallyl, 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 -Cg alkynyl, and the alkynyl parts of C 3 -Cg alkynylcarbonyl, C 3 -Cg alkynyloxy, C 3 -Cg alkynyloxycarbonyl, C 3 -Cg alkynylaminocarbonyl, N- (
  • C 3 -Cg haloalkynyl a C 3 -Cg 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-1-yl, 4-iodo-but-3-in-1-yl, 5-fluoropent-3-in-1-yl, 5-iodo-pent-4-in-1-yl, 6-fluorine hex-4-in-l-yl or 6-iodo-hex-5-in-l-yl;
  • C 3 -Cg cycloalkyl and the cycloalkyl parts of C 3 -Cg cycloalkylcarbonyl: for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;
  • heterocyclyl and also heterocyclyl parts of heterocyclylcarbonyl, heterocyclyl-Ci-Cg-alkyl, heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl, heterocyclylcarbonyl-Ci-Cg-alkyl, N- (Ci-Cg-alkylclycylyl) -N- (hetero- minocarbonyl: a saturated, partially saturated or unsaturated 5- or 6-membered, C-bonded, heterocyclic ring which contains one to four identical or different heteroatoms selected from the following group: oxygen, sulfur or nitrogen, so for example 5-membered rings with one heteroatom:
  • 5-membered rings with 2 heteroatoms such as: tetrahydropyrazole-3-yl, tetrahydropyrazol-4-yl, tetrahydroisoxazol-3-yl, tetrahydroisoxazol-4-yl, tetrahydroisoxazol-5-yl, 1,2-oxathiolane -yl, 1,2-oxathiolan-4-yl, 1,2-oxathiolan-5-yl, tetrahydroisothiazol-3-yl, tetrahydroisothiazol-4-yl, tetrahydroisothiazol-5-yl, 1,2-dithiolane -3- yl, 1,2-dithiolan-4-yl, tetrahydroimidazol-2-yl, tetrahydroimidazol-4-yl, tetrahydrooxazol-2-yl, tetrahydroo
  • 5-membered rings with 3 heteroatoms such as: 1, 2, 3- ⁇ 2 -oxadiazo-lin-4-yl, 1, 2, 3- ⁇ 2 -oxadiazolin-5-yl, 1, 2, 4- ⁇ 4 - Oxadiazo-lin-3-yl, 1, 2, 4- ⁇ 4 -oxadiazolin-5-yl, 1, 2, 4- ⁇ 2 -Oxadiazo-lin-3-yl, 1, 2, 4- ⁇ 2 -oxadiazolin -5-yl, 1, 2, 4- ⁇ 3 -Oxadiazo-lin-3-yl, 1, 2, 4- ⁇ 3 -Oxadiazolin-5-yl, 1, 3, 4- ⁇ 2 -Oxadiazo- lin- 2-yl, 1, 3, 4- ⁇ 2 -oxadiazolin-5-yl, 1, 3, 4- ⁇ 3 -oxadiazolin-2-yl, 1, 3, 4- ⁇ 3 -oxadiazolin-2-yl, 1, 3, 4- ⁇ 3 -oxadiazolin-2-yl, 1, 3, 4-o
  • 6-membered rings with a heteroatom such as:
  • 6-membered rings with two heteroatoms such as: 1, 3-dioxan-2-yl,
  • 6-membered rings with 3 heteroatoms such as: 1, 3, 5-triazin-2-yl, l, 2,4-triazin-3-yl, 1, 2, 4-triazin-5-yl or 1,2,4 -Triazine-6-yl;
  • 6-membered rings with 4 heteroatoms such as: l, 2,4,5-tetrazin-3-yl;
  • a bicyclic ring system can be formed with a fused-on phenyl ring or with a C 3 -Cg 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:
  • 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-di
  • Phthalimide tetrahydrophthalimide, succinimide, maleimide or glutarimide
  • the variables preferably have the following meanings, in each case individually or in combination:
  • R 1 nitro, halogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl,
  • R 3 is hydrogen
  • R 4 , R 5 are hydrogen, halogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, Ci-Cg-alkylthio,
  • Ci-Cg-haloalkylthio Ci-Cg-alkylsulfonyl or Ci-Cg-haloalkylsulfonyl;
  • R 4 and R 5 together form a -0- (CH 2 ) m -0-, -0- (CH 2 ) m -S-,
  • -S- (CH) m -S- or -0- (CH 2 ) n chain which can be substituted by one to three radicals from the following group: halogen, cyano, C 1 -C 4 alkyl, C 1 - C 4 haloalkyl or C 1 -C 4 alkoxycarbonyl;
  • R 4 and R 5 together form a - (CH 2 ) p chain, which can be interrupted by oxygen or sulfur and / or can be substituted by one to four radicals from the following group:
  • R 4 and R 5 together form a methylidene group, which can be substituted by one or two radicals from the following group:
  • R 7 is a compound Ha or Ilb
  • R 8 halogen, OR 10 , SR 10 , S0 2 R 1: L ⁇ OS0 2 R 1: L , OPOR 11 R 12 , OPSR 11 R 12 ,
  • NR 13 R 14 ONR 1 R 14 , N-linked heterocyclyl or 0- (N-linked heterocyclyl), where the heterocyclyl radical of the latter two substituents can be partially or completely halogenated and / or can carry one to three of the following radicals :
  • R 9 halogen, cyano, Ci-Cg-alkyl, Ci-Cg-haloalkyl, di- (Ci-Cg-alkoxy) -methyl, di- (Ci-Cg-alkylthio) -methyl,
  • Ci-Cg-alkoxy (Ci-Cg-alkoxy) (Ci-Cg-alkylthio) methyl, hydroxy, Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, Ci-Cg-alkylthio, Ci-Cg-haloalkylthio, Ci-Cg-alkylsulfonyl, C ⁇ ⁇ Cg-haloalkylsulfonyl, Ci-Cg-alkylcarbonyl, Ci-Cg-haloalkylcarbonyl, Ci-Cg-alkoxycarbonyl or Ci-Cg-haloalkoxycarbonyl;
  • radicals R 9 which are bonded to the same carbon, together form a -0- (CH 2 ) m -0-, -0- (CH) m -S -, -S- (CH 2 ) m -S- or -0- (CH 2) n chain which may be substituted from the following group by one to three radicals: halogen, cyano, C 4 alkyl, Ci -C4 haloalkyl or
  • R 9 radicals which are bonded to the same carbon together form a - (CH 2 ) p chain which can be interrupted by oxygen or sulfur and / or can be substituted by one to four radicals from the following group: halogen, cyano , -C-C4 alkyl, C 1 -C 4 haloalkyl or
  • R 9 radicals which are bonded to different carbons, together form a - (CH) n chain, which can be substituted by one to three radicals from the following group: halogen, Ci-Cg-alkyl, Ci-Cg -alkoxy, Hydroxy or
  • R 10 Ci-Cg-alkyl, C 3 -Cg-alkenyl, C 3 -Cg-haloalkenyl,
  • R 11 , R 12 Ci-Cg-alkyl, C 3 -Cg-alkenyl, C 3 -C 6 -haloalkenyl, C -Cg-cycloalkyl, hydroxy, Ci-Cg-alkoxy or di- (Ci-Cg-haloalkyl) amino , the said
  • Alkyl, cycloalkyl and alkoxy radicals can be partially or completely halogenated and / or can carry one to three of the following groups: cyano, C 4 -C 4 -alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylcarbonyl, C 1 -C 4 alkoxycarbonyl, hydroxycarbonyl,
  • Phenyl and the heterocyclyl radical of the lastmentioned substituents may be partially or fully halogenated and / or may carry one to three of the following radicals: nitro, cyano, C 4 -alkyl, C 4 haloalkyl,
  • R 13 Ci-Cg-alkyl, C 3 -C -alkenyl, C 3 -Cg-haloalkenyl,
  • R 14 Ci-Cg-alkyl or C 3 -Cg-alkenyl
  • R 1 is halogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkoxy, Ci-Cg-alkylthio or Ci-Cg-alkylsulfonyl; in particular halogen such as chlorine or bromine, -CC 5 alkyl such as methyl or ethyl or Ci-Cg-alkoxy such as methoxy or ethoxy; particularly preferably chlorine, methyl or methoxy;
  • R 3 is hydrogen
  • R, R 5 is hydrogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkoxy or Ci-Cg-haloalkoxy, especially hydrogen, Ci-Cg-alkyl or Ci-Cg-alkoxy; particularly preferably hydrogen or Ci-Cg-alkyl such as
  • R 4 and R 5 together form a -0- (CH 2 ) m -0-, -0- (CH 2 ) m -S- or -S- (CH) m -S chain, which consists of one to three radicals can be substituted from the following group: C 1 -C 4 alkyl or C 1 -C 4 haloalkyl; or
  • R 4 and R 5 together form a - (CH) p chain, which can be substituted by one to four radicals from the following group:
  • Halogen C 1 -C 4 alkyl or C 1 -C 4 haloalkyl
  • R 4 and R 5 together form a methylidene group, which can be substituted by one or two radicals from the following group:
  • R 7 is a compound Ha or Ilb
  • R8 halogen, OR 10 , SR 10 , S0 2 R 1: L ⁇ OS0 2 R 11 , NR 13 R 14 , ONR 1 R 14 ,
  • R 9 halogen, cyano, Ci-Cg-alkyl, Ci-Cg-haloalkyl,
  • R 11 , R 12 Ci-Cg-alkyl, C 3 -Cg-alkenyl, C 3 -Cg-haloalkenyl, C 3 -Cg-cycloalkyl, hydroxy, Ci-Cg-alkoxy or di- (Ci-Cg-haloalkyl) amino , where the alkyl, cycloalkyl and alkoxy radicals mentioned can be partially or completely halogenated and / or can carry one to three of the following groups: cyano, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 - Alkyl carbonyl, -C 4 alkoxycarbonyl, hydroxycarbonyl, di (-C 4 alkyl) aminocarbonyl, -C 4 alkylcarbonyloxy or C 3 -Cg cycloalkyl; Phenyl, heterocyclyl, phenyl-Ci-Cg-alkyl, heterocyclyl-C
  • R 13 Ci-Cg alkyl, C 3 -Cg alkenyl, C 3 -Cg haloalkenyl,
  • R 14 Ci-Cg alkyl or C 3 -C alkenyl
  • R 4 is hydrogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkoxy or Ci-Cg-haloalkoxy; particularly preferably hydrogen, Ci-Cg-alkyl such as methyl or ethyl or Ci-Cg-alkoxy such as methoxy or ethoxy;
  • R 5 is hydrogen or C 1 -C 6 -alkyl; particularly preferably hydrogen or methyl;
  • R 4 and R 5 together form a -0- (CH 2 ) 2 -0-, -0- (CH 2 ) 3 -0-,
  • R 4 and R 5 together form a methylidene group which can be substituted by a radical from the following group:
  • Halogen such as chlorine or bromine
  • Ci-Cg-alkyl such as methyl or ethyl
  • Ci-Cg-haloalkyl such as chloromethyl, fluoromethyl, dichloromethyl, difluoromethyl or trifluoromethyl
  • Ci-Cg-alkoxy such as methoxy or ethoxy.
  • R 4 is hydrogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkoxy or Ci-Cg-haloalkoxy; particularly preferably hydrogen, Ci-Cg-alkyl such as methyl or ethyl or Ci-Cg-alkoxy such as methoxy or ethoxy;
  • R 5 is hydrogen or Ci-Cg-alkyl; particularly preferably hydrogen or methyl;
  • R 9 nitro, halogen, cyano, Ci-Cg-alkyl, Ci-Cg-haloalkyl, di- (Ci-Cg-alkoxy) -methyl, di- (Ci-Cg-alkylthio) -methyl, (Ci-Cg-alkoxy ) (Ci-Cg-alkylthio) methyl, hydroxy, Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, Ci-Cg-alkylthio, Ci-Cg-haloalkylthio, Ci-Cg-alkylsulfinyl, Ci-Cg-haloalkylsufinyl, Ci -C -alkylsulfonyl, Ci-Cg-haloalkylsulfonyl, Ci-Cg-alkylcarbonyl, Ci-Cg-haloalkylcarbonyl, Ci-Cg-alkoxycarbonyl or Ci-Cg-halo
  • R 9 radicals which are bonded to the same carbon together form a -0- (CH 2 ) m -0-, -0- (CH 2 ) m - S -, - S - (CH 2 ) m - S - or -0- (CH 2 ) n chain, which can be substituted by one to three radicals from the following group: halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or
  • radicals R which are bonded to the same carbon form a - (CH 2 ) p chain which can be interrupted by oxygen or sulfur and / or can be substituted by one to four radicals from the following group: halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 alkoxycarbonyl;
  • R 9 nitro, halogen, cyano, Ci-Cg-alkyl, Ci-Cg-haloalkyl,
  • R 8 NR 13 R 14 or N-bonded heterocyclyl which may be partially or fully halogenated and / or may carry one to three of the following radicals: nitro, cyano, C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or Ci -C 4 haloalkoxy;
  • Heterocyclyl radical can be partially or completely halogenated and / or can carry one to three of the following radicals:
  • the compounds of the formula Ia are also particularly preferred.
  • R 1 is halogen or C 1 -C 6 -alkyl; especially chlorine, bromine or C 1 -C 4 alkyl; particularly preferably chlorine or methyl;
  • R 3 is hydrogen
  • R 4 is hydrogen, Ci-Cg alkyl or Ci - C ⁇ alkoxy; in particular Ci-Cg-alkyl or Ci-Cg-alkoxy; particularly preferably methyl or methoxy;
  • R 5 is hydrogen or Ci-Cg alkyl: in particular hydrogen or methyl
  • R 8 halogen, OR 10 , SR 10 , SO 2 R 11 , NR 13 R 14 or N-linked
  • Heterocyclyl where the heterocyclyl radical may be partially or fully halogeninstrument and / or may carry one to three of the following radicals: nitro, cyano, C 4 alkyl, C 1 -C 4 haloalkyl,
  • R 9 Ci-C-alkyl, such as methyl or ethyl; especially methyl;
  • R 13 Ci-Cg-alkyl, such as methyl or ethyl
  • R 14 Ci-Cg alkoxy, such as methoxy or ethoxy
  • R 8 halogen, OR 10 , SR 10 , S0 2 R 1X , NR 13 R 14 , 4 -morpholinyl,
  • Table 1 :
  • the compounds of the formulas Ia7 and Ib7 in particular the compounds Ia7.1 to Ia7.342 and the compounds Ib7.1 to Ib7.342, which differ from the compounds Ial.l to Ial.342 or Ibl.l to Ibl.342 differ in that (R 9 ) q means "6-methyl".
  • the compounds IalO and IblO in particular the compounds IalO.l to IalO.456 and IblO.l to IblO.456, which differ from the compounds Ia9.1 to Ia9.456 or Ib9.1 to Ib9.456 that R 1 represents chlorine is extremely preferred.
  • the compounds Iall and Ibll in particular the compounds Iall.l to Iall.456 and Ibll.l to Ibll.456, which differ from the compounds Ia9.1 to Ia9.456 or Ib9.1 to Ib9.456 differ in that R 1 is methoxy, extremely preferred.
  • the compounds Ia in particular the compounds Ial to Iall, and the embodiments mentioned in each case are also extremely preferred.
  • cyclohexenone dioxothiochromanoyl derivatives of the formula I can be obtained in various ways, for example by the following processes:
  • halogenating agents examples include phosgene, diphosgene, triphosgene, thionyl chloride, oxalyl chloride, phosphorus oxychloride, phosphorus pentachloride, mesyl chloride, chloromethylene-N, N-dimethylammonium chloride, oxylyl bromide, phosphorus oxybromide etc.
  • the output connections are usually used in an equimolar ratio. However, it can also be advantageous to use one or the other component in excess.
  • solvents examples include chlorinated hydrocarbons such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons e.g. Toluene, xylene or chlorobenzene, polar aprotic solvents, such as acetonitrile, dimethylformamide or dimethyl sulfoxide, or mixtures thereof.
  • chlorinated hydrocarbons such as methylene chloride or 1,2-dichloroethane
  • aromatic hydrocarbons e.g. Toluene, xylene or chlorobenzene
  • polar aprotic solvents such as acetonitrile, dimethylformamide or dimethyl sulfoxide, or mixtures thereof.
  • the reaction can also be carried out in bulk.
  • reaction temperature is in the range from 0 ° C. to the boiling point of the reaction mixture.
  • the product can be worked up in a manner known per se.
  • L 1 stands for a nucleophilically displaceable leaving group, such as halogen, e.g. B. chlorine or bromine, hetaryl, e.g. B. imidazolyl, carboxylate, e.g. B. acetate, or sulfonate, e.g. B. mesylate or triflate etc.
  • halogen e.g. 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 IV ⁇ , IVß, IV ⁇ or IV ⁇ 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.).
  • the starting compounds are generally used in an equimolar ratio. However, it can also be advantageous to use one or the other component in excess.
  • the reactants and the base are expediently used in equimolar amounts.
  • An excess of the base e.g. 1.5 to 3 molar equivalents can be advantageous under certain circumstances.
  • Suitable bases are tertiary alkyl amines such as triethylamine, aromatic amines such as pyridine, alkali metal carbonates, e.g. Sodium carbonate or potassium carbonate, alkali metal hydrogen carbonates, such as sodium hydrogen carbonate and potassium hydrogen carbonate, alkali metal alcoholates such as sodium methoxide,
  • Sodium ethanolate, potassium tert. butanolate or alkali metal hydrides e.g. Sodium hydride.
  • Triethylamine or pyridine are preferably used.
  • solvents examples include chlorinated hydrocarbons such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons e.g. Toluene, xylene or chlorobenzene, ethers such as diethyl ether, methyl tert. -butyl ether, tetrahydrofuran or dioxane, polar aprotic solvents such as acetonitrile, dimethylformamide or dimethyl sulfoxide or
  • Esters such as ethyl acetate, or mixtures thereof.
  • reaction temperature is in the range from 0 ° C. to the boiling point of the reaction mixture.
  • the product can be worked up in a manner known per se.
  • HPOR 1 L R 12 v ⁇ heterocyclyl or or 0- (N-linked heterocyclyl))
  • the starting compounds are generally used in an equimolar ratio. However, it can also be advantageous to use one or the other component in excess.
  • the reactants and the base are expediently used in equimolar amounts.
  • Suitable bases are tertiary alkyl amines, such as tertiary
  • Alkyl amines such as pyridine, alkali metal carbonates, e.g. Sodium carbonate or potassium carbonate, alkali metal bicarbonates such as sodium bicarbonate and potassium bicarbonate, alkali metal alcoholates such as sodium methoxide, sodium methoxide, potassium tert. butanolate or alkali metal hydrides, e.g. Sodium hydride. Sodium hydroxide or potassium tert are preferably used. -butylate.
  • solvents examples include chlorinated hydrocarbons, such as methylene chloride or 1,2-dichloroethane, aromatic
  • Hydrocarbons for example 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 mixtures thereof.
  • the reaction temperature is in the range from 0 ° C. to the boiling point of the reaction mixture.
  • the product can be worked up in a manner known per se.
  • Suitable oxidizing agents are m-chloroperbenzoic acid, peroxyacetic acid, trifluoroperoxyacetic acid, hydrogen peroxide, if appropriate in the presence of a catalyst such as tungstate.
  • the starting compounds are generally used in an equimolar ratio. However, it can also be advantageous to use one or the other component in excess.
  • solvents examples include chlorinated hydrocarbons such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons e.g. Toluene, xylene or chlorobenzene, ethers such as diethyl ether, methyl tert. -butyl ether, tetrahydrofuran or dioxane, polar aprotic solvents such as acetonitrile, dimethylformamide or esters such as ethyl acetate, or mixtures thereof.
  • chlorinated hydrocarbons such as methylene chloride or 1,2-dichloroethane
  • aromatic hydrocarbons e.g. Toluene, xylene or chlorobenzene
  • ethers such as diethyl ether, methyl tert. -butyl ether, tetrahydrofuran or dioxane
  • polar aprotic solvents such as acetonitrile, dimethylformamide or est
  • reaction temperature is in the range from 0 ° C. to the boiling point of the reaction mixture.
  • the product can be worked up in a manner known per se.
  • compounds la, Ib or mixtures thereof can be formed.
  • the latter can be separated using classic separation methods, e.g. Crystallization, chromatography, etc., are separated.
  • cyclohexanedione derivatives of the formula III are known or can be prepared by processes known per se (e.g.
  • L 2 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 Vlla benzoic acid 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. 1.2 to 1.5 molar equivalents, based on VII, can be advantageous under certain circumstances.
  • Tertiary alkyl amines, pyridine or alkali metal carbonates are suitable as auxiliary bases.
  • solvents which can be used are 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, tetra- hydrofuran or dioxane, polar aprotic solvents such as acetonitrile, dimethylformamide or dimethyl sulfoxide or esters such as ethyl acetate or mixtures thereof.
  • 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 rearrangement without further purification.
  • the rearrangement of the esters to the compounds of the formula III 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 catalyst.
  • solvent e.g. Acetonitrile, methylene chloride, 1, 2-dichloroethane, dioxane, ethyl acetate, toluene or mixtures thereof can be used.
  • 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 10 mol percent, based on the ester.
  • the reaction mixture is acidified, for example with dilute mineral acid, such as 5% hydrochloric acid or sulfuric acid, and extracted with an organic solvent, for example methylene chloride or ethyl acetate.
  • the organic extract can contain 5-10% Alkali carbonate solution, for example sodium carbonate or potassium carbonate solution.
  • the aqueous phase is acidified and the precipitate that forms is filtered off with suction and / or extracted with methylene chloride or ethyl acetate, dried and concentrated.
  • halogenating reagents such as thionyl chloride, 10 thionyl bromide, phosgene, diphosgene, triphosgene, oxalyl chloride, oxalyl bromide.
  • the benzoic acids of the formula VIIIb can be prepared in a known manner from the corresponding esters by acidic or basic hydrolysis.
  • Step d) 4, 4, 8-trimethyl-l, l-dioxothiochroman-7-carboxylic acid
  • the compounds of formula I and their agriculturally useful salts are suitable both as isomer mixtures and in the form of the pure isomers - as herbicides.
  • the herbicidal compositions which contain compounds of the formula I control vegetation very well on non-cultivated areas, especially when high amounts are applied. In crops such as wheat, rice, corn, soybeans and cotton, they act against weeds and grass weeds without significantly damaging the crop plants. This effect occurs above all at low application rates.
  • the compounds of the formula I or herbicidal compositions comprising them can also be used in a further number of crop plants for eliminating undesired plants.
  • the following crops are considered, for example:
  • Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarle, Seeale Solanum tuberosum, sorghum bicolor (see vulgar), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.
  • the compounds of the formula I can also be used in crops which are tolerant to the action of herbicides by breeding, including genetic engineering methods.
  • the compounds of the formula I or the herbicidal compositions comprising them can be used, for example, in the form of directly sprayable aqueous solutions, powders, suspensions, including high-strength aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, Scattering agents or granules can be applied by spraying, atomizing, 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.
  • the herbicidal compositions comprise a herbicidally effective amount of at least one compound of the formula I or an agriculturally useful salt of I and auxiliaries customary for the formulation of crop protection agents.
  • Mineral oil fractions of medium to high boiling point such as kerosene and diesel oil, also coal tarols and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Paraffin, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes or their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, strongly polar solvents, e.g. Amines such as N-methylpyrrolidone and water.
  • Paraffin tetrahydronaphthalene
  • alkylated naphthalenes and their derivatives alkylated benzenes or their derivatives
  • alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol
  • ketones such as cyclohexan
  • Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water.
  • the cyclohexenone dioxothiochromanoyl derivatives of the formula I 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 can also consist of active substance, wetting, adhesive,
  • Dispersants or emulsifiers and possibly solvents or oil existing concentrates are prepared which are suitable for dilution with water.
  • the surface-active substances are the alkali, alkaline earth, 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 sulfated hexa-, hepta- and octadecanols as well as fatty alcohol glycol ether, 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, phenyl or nonyl phenyl Tributy
  • Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
  • Granules e.g. Coated, impregnated and homogeneous granules can be produced by binding the active ingredients to solid carriers.
  • Solid carriers are mineral soils such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, Ammonium nitrate, ureas and vegetable products such as corn flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
  • concentrations of the compounds of the formula I in the ready-to-use preparations can be varied within a wide range.
  • the formulations contain from about 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 application rates of the compound of the formula I are, depending on the control target, the season, the target plants and the growth stage, 0.001 to 3.0, preferably 0.01 to 1.0 kg / ha of active substance (a.S.).
  • cyclohexenone dioxothiochromanoyl derivatives of the formula I can be mixed with numerous representatives of other herbicidal or growth-regulating active compound groups and applied together.
  • pyrazoles Derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and their derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides and uracils.
  • Plastic flower pots with loamy sand with about 3.0% humus as substrate served as culture vessels.
  • the seeds of the test plants were sown separately according to species.
  • the active ingredients suspended or emulsified in water were applied directly after sowing using finely distributing nozzles.
  • the tubes were lightly sprinkled to promote germination and growth, and then covered with 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 For the purpose of post-emergence treatment, the test plants, depending on the growth habit, were first grown to a height of 3 to 15 cm and only 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. (active substance).
  • the plants were kept in a species-specific manner at temperatures of 10 to 25 ° C and 20 to 35 ° C.
  • the trial period lasted 2 to 4 weeks. During this time, the plants were cared for and their response to each treatment was evaluated.
  • 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 cyclohexenondioxothiochromanoyl derivatives of formula (I) wherein the variables have the following meanings: X is oxygen, sulphur, S=O, S(=O)2, CR4R5, C=O or C=NR6; R1 is hydrogen, nitro, halogen, cyano, alkyl, alkyl halide, alkoxy, halogenalkoxy, alkylthio, halogenalkylthio, alkylsulfinyl, halogenalkylsulfinyl, alkylsulfonyl, halogenalkylsulfonyl, optionally substituted aminosulfonyl or optionally substituted sulfonylamino; R2 is alkyl, alkyl halide, alkoxy or halogenalkoxy; R3 is hydrogen, alkyl or halogen; and R4, R5 are hydrogen, nitro, halogen, cyano, alkyl, alkyl halide, alkoxy, halogenalkoxy, alkylthio, halogenalkylthio, alkylsulfinyl, halogenalkylsulfinyl, alkylsulfonyl, halogenalkylsulfonyl or substituted amino; or R?4 and R5¿ together form a chain which can be substituted and/or interrupted by oxygen or sulphur; or an optionally substituted methylide group; l is 0 to 4; R7 is substituted (3-oxo-1-cyclohexen-2-yl)-carbonyl or substituted (1,3-dioxo-2-cyclohexyl-methylides. The invention also relates to the agriculturally usable salts of said derivatives, to methods for producing the derivatives, to substances containing them, and to the use of the derivatives or substances containing them for combating undesirable plants.

Description

Cyclo exenondioxot iochromanoyl-DerivateCyclo exenondioxot iochromanoyl derivatives
Beschreibungdescription
Die vorliegende Erfindung betrifft neue Cyclohexenondioxothio- chromanoyl -Derivate der Formel I,The present invention relates to new cyclohexenone dioxothio-chromanoyl derivatives of the formula I,
in der die Variablen folgende Bedeutung haben:in which the variables have the following meaning:
X Sauerstoff, Schwefel, S=0, S(=0)2, CR4R5, C=0 oderX oxygen, sulfur, S = 0, S (= 0) 2 , CR 4 R 5 , C = 0 or
C=NR6;C = NR 6 ;
R1 Wasserstoff, Nitro, Halogen, Cyano, Cι-C6-Alkyl,R 1 is hydrogen, nitro, halogen, cyano, -CC 6 alkyl,
Ci-Cß-Halogenalkyl, Ci-Cg-Alkoxy, Ci-Cg-Halogenalkoxy, Cι-C6-Alkylthio, Cι-C6-Halogenalkylthio, Cι-C6-Alkyl- sulfinyl, Ci-Cδ-Halogenalkylsulfinyl, Ci-Cδ-Alkyl- sulfonyl, Cι-C6-Halogenalkylsulfonyl, Aminosulfonyl, N- (Ci-Ce-Alkyl) -aminosulfonyl, N, N-Di- (Cι-C6-alkyl) - aminosulfonyl, N- (Ci-Cg-Alkylsulfonyl) -amino, N- (Ci-Cg-Halogenalkylsulfonyl) -amino, N- (Ci-Cg-Alkyl) - N- (Cι-C6-alkylsulfonyl) -amino oder N- (Ci-Cg-Alkyl) -N- (Ci-Cß-Halogenalkylsulfonyl) -amino;Ci-C ß -haloalkyl, Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, Cι-C 6 alkylthio, Cι-C 6 -haloalkylthio, Cι-C 6 alkylsulfinyl, Ci-C δ -haloalkylsulfinyl, Ci -C δ alkyl sulfonyl, -C-C 6 haloalkylsulfonyl, aminosulfonyl, N- (Ci-Ce-alkyl) -aminosulfonyl, N, N-di- (Cι-C 6 alkyl) - aminosulfonyl, N- (Ci -Cg-alkylsulfonyl) -amino, N- (Ci-Cg-haloalkylsulfonyl) -amino, N- (Ci-Cg-alkyl) - N- (-Cι-C 6 -alkylsulfonyl) -amino or N- (Ci-Cg- Alkyl) -N- (Ci-C ß -haloalkylsulfonyl) amino;
R2 Ci-Cg-Alkyl, Cι-C6 -Halogenalkyl, Cχ-Cg-Alkoxy oder Ci- Cζ -Halogenalkoxy;R 2 Ci-Cg-alkyl, -CC 6 -haloalkyl, Cχ-Cg-alkoxy or Ci-Cζ -haloalkoxy;
R3 Wasserstoff, Ci-Cg-Alkyl oder Halogen;R 3 is hydrogen, Ci-Cg-alkyl or halogen;
R4,R5 Wasserstoff, Nitro, Halogen, Cyano, Cχ-Cg-Alkyl,R 4 , R 5 are hydrogen, nitro, halogen, cyano, Cχ-Cg-alkyl,
Ci-Cß-Halogenalkyl, Ci-Cg-Alkoxy, Ci-Cg-Halogenalkoxy, Cι-C6-Alkylthio, Cι-C6-Halogenalkylthio, Ci-Cg-Alkyl- sulfinyl, Cχ-Cg-Halogenalkylsulfinyl, C]_-Cg-Alkyl- sulfonyl, Ci-Cg-Halogenalkylsulfonyl, N-Ci-Cg-Alkyl- amino, N-Ci-Cg-Halogenalkylamino, N, N-Di - (Ci-Cg -alkyl) amino, N-Ci-Cg-Alkoxyamino, N- (Ci -Cg-Alkoxy) -N- (Cι-C6- alkyl) amino, 1-Tetrahydropyrrolyl, 1-Piperidinyl, 4 -Morpholinyl oder 1-Hexahydropyrazinyl;Ci-C ß -haloalkyl, Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, Cι-C 6 -alkylthio, Cι-C 6 -haloalkylthio, Ci-Cg-alkylsulfinyl, Cχ-Cg-haloalkylsulfinyl, C] _ -Cg-alkyl-sulfonyl, Ci-Cg-haloalkylsulfonyl, N-Ci-Cg-alkylamino, N-Ci-Cg-haloalkylamino, N, N-Di - (Ci-Cg -alkyl) amino, N-Ci- Cg-alkoxyamino, N- (Ci -Cg-alkoxy) -N- (-C-C 6 - alkyl) amino, 1-tetrahydropyrrolyl, 1-piperidinyl, 4-morpholinyl or 1-hexahydropyrazinyl;
oder R4 und R5 bilden gemeinsam eine -0- (CH2) m-0- , -O- (CH2)m-S - ,or R 4 and R 5 together form a -0- (CH 2 ) m -0-, -O- (CH 2 ) m -S -,
-S-(CH )m-S- oder -0- (CH ) n-Kette, die durch einen bis drei Reste aus folgender Gruppe substituiert sein kann: Halogen, Cyano, Cι-C -Alkyl, Cι-C -Halogenalkyl oder Cι-C -Alkoxycarbonyl;-S- (CH) m -S- or -0- (CH) n chain, which can be substituted by one to three radicals from the following group: halogen, cyano, C 1 -C 4 -alkyl, C 1 -C 6 -haloalkyl or -C -alkoxycarbonyl;
oderor
R4 und R5 bilden gemeinsam eine - (CH2)p-Kette, die durch Sauer- stoff oder Schwefel unterbrochen sein kann und/oder durch einen bis vier Reste aus folgender Gruppe substituiert sein kann:R 4 and R 5 together form a - (CH 2 ) p chain, which can be interrupted by oxygen or sulfur and / or can be substituted by one to four radicals from the following group:
Halogen, Cyano, Cχ-C4-Alkyl, C1-C4 -Halogenalkyl oder C_.-C4-Alkoxycarbonyl ;Halogen, cyano, Cχ-C 4 alkyl, C 1 -C 4 haloalkyl or C_ . -C 4 alkoxycarbonyl;
oderor
R4 und R5 bilden gemeinsam eine Methylidengruppe, die durch einen bis zwei Reste aus folgender Gruppe substituiert sein kann:R 4 and R 5 together form a methylidene group, which can be substituted by one or two radicals from the following group:
Halogen, Hydroxy, Formyl, Cyano, Cχ-Cg-Alkyl, Cι-C6-Halogenalkyl, Cι-C5-Alkoxy, Ci-Cg-Halogenalkoxy, Ci-Cg-Alkylthio, Ci-Cg-Halogenalkylthio, Ci-Cg-Alkyl- sulfinyl, Ci-Cg-Halogenalkylsulfinyl , Ci-Cg-Alkyl- sulfonyl oder Ci-Cg-Halogenalkylsulfonyl ;Halogen, hydroxy, formyl, cyano, Cχ-Cg-alkyl, Cι-C 6 -haloalkyl, Cι-C 5 -alkoxy, Ci-Cg-haloalkoxy, Ci-Cg-alkylthio, Ci-Cg-haloalkylthio, Ci-Cg- Alkylsulfinyl, Ci-Cg-haloalkylsulfinyl, Ci-Cg-alkylsulfonyl or Ci-Cg-haloalkylsulfonyl;
R6 Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, Ci-Cg-Alkoxy oder Ci-Cg-Halogenalkoxy;R 6 Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkoxy or Ci-Cg-haloalkoxy;
1 0 bis 4;1 0 to 4;
m 2 bis 4;m 2 to 4;
n 1 bis 5;n 1 to 5;
p 2 bis 5;p 2 to 5;
R7 eine Verbindung Ha oder IlbR 7 is a compound Ha or Ilb
wobei R8 Halogen, OR10, SR10, SOR11- S02R11- OS02R11, POR^R12, in which R8 halogen, OR 10 , SR 10 , SOR 11 - S0 2 R 11 - OS0 2 R 11 , POR ^ R 12 ,
OPOR^R12, OPSR11R12, NR13R14, ONR1Ri4 , N-gebundenes Heterocyclyl oder 0- (N-gebundenes Heterocyclyl) , wobei der Heterocyclyl -Rest der beiden letztgenannten Substi- tuenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann:OPOR ^ R 12 , OPSR 11 R 12 , NR 13 R 14 , ONR 1 R i4 , N-linked heterocyclyl or 0- (N-linked heterocyclyl), the heterocyclyl radical of the latter two substituents being partially or completely halogenated can and / or can carry one to three of the following residues:
Nitro, Cyano, C1-C4 -Alkyl, C1-C4 -Halogenalkyl, C1-C4-AI- koxy oder C1-C4 -Halogenalkoxy;Nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 AI koxy or C 1 -C 4 haloalkoxy;
R9 Nitro, Halogen, Cyano, Ci-Cg-Alkyl, Cι-C6-Halogenalkyl, Di- (Ci-Cg-alkoxy) -methyl, Di- (Ci-Cg-alkylthio) -methyl, (Ci-C -Alkoxy) (Ci-Cg-alkylthio) -methyl, Hydroxy, Ci-Cg-Alkoxy, Ci-Cg-Halogenalkoxy, C -Cg-Alkylthio, Ci-Cg-Halogenalkylthio, Ci-Cg-Alkylsulfinyl, Ci-Cg-R 9 nitro, halogen, cyano, Ci-Cg-alkyl, Cι-C 6 -haloalkyl, di- (Ci-Cg-alkoxy) -methyl, di- (Ci-Cg-alkylthio) -methyl, (Ci-C - Alkoxy) (Ci-Cg-alkylthio) methyl, hydroxy, Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, C -Cg-alkylthio, Ci-Cg-haloalkylthio, Ci-Cg-alkylsulfinyl, Ci-Cg-
Halogenalkylsulfinyl, Ci-Cg-Alkylsulfonyl, Ci-Cg- Halogenalkylsulfonyl, Ci-Cg-Alkylcarbonyl, Cι~Cg-Halo- genalkylcarbonyl, Ci-Cg-Alkoxycarbonyl oder Ci-Cg-Halo- genalkoxycarbonyl ;Haloalkylsulfinyl, Ci-Cg-alkylsulfonyl, Ci-Cg-haloalkylsulfonyl, Ci-Cg-alkylcarbonyl, Ci-Cg-haloalkylcarbonyl, Ci-Cg-alkoxycarbonyl or Ci-Cg-haloalkoxycarbonyl;
oderor
zwei Reste R9 , die am gleichen Kohlenstoff gebunden sind, bilden gemeinsam eine -0- (CH2)m-0- , -0- (CH2)m-S- , -S-(CH2)m-S- oder -0- (CH ) n-Kette, die durch einen bis drei Reste aus folgender Gruppe substituiert sein kann: Halogen, Cyano, C1-C4 -Alkyl, C1-C4 -Halogenalkyl oder C -C4 -Alkoxycarbonyl ;two radicals R 9 , which are bonded to the same carbon, together form a -0- (CH 2 ) m -0-, -0- (CH 2 ) m -S-, -S- (CH 2 ) m -S- or -0- (CH) n chain, which can be substituted by one to three radicals from the following group: halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C -C 4 alkoxycarbonyl ;
oderor
zwei Reste R9 , die am gleichen Kohlenstoff gebunden sind, bilden gemeinsam eine - (CH2)p-Kette, die durch Sauerstoff oder Schwefel unterbrochen sein kann und/oder durch einen bis vier Reste aus folgender Gruppe substituiert sein kann:two R 9 radicals which are bonded to the same carbon together form a - (CH 2 ) p chain which can be interrupted by oxygen or sulfur and / or can be substituted by one to four radicals from the following group:
Halogen, Cyano, C1-C4 -Alkyl, C1-C4 -Halogenalkyl oder Ci -C4 -Alkoxycarbonyl ;Halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or Ci -C 4 alkoxycarbonyl;
oderor
zwei Reste R9 , die am gleichen Kohlenstoff gebunden sind, bilden gemeinsam eine Methylidengruppe, die durch einen bis zwei Reste aus folgender Gruppe substituiert sein kann: Halogen, Hydroxy, Formyl, Cyano, Ci-Cg-Alkyl,two R 9 radicals which are bonded to the same carbon together form a methylidene group which can be substituted by one or two radicals from the following group: halogen, hydroxy, formyl, cyano, Ci-Cg-alkyl,
Ci-Cg-Halogenalkyl, Ci-Cg-Alkoxy, Ci-Cg-Halogenalkoxy, Ci-Cg-Alkylthio, Ci-Cg-Halogenalkylthio, Ci-Cg-Alkyl- sulfinyl, Ci-Cg-Halogenalkylsulfinyl , Ci-Cg-Alkyl- sulfonyl, Ci-Cg-Halogenalkylsulfonyl;Ci-Cg-haloalkyl, Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, Ci-Cg-alkylthio, Ci-Cg-haloalkylthio, Ci-Cg-alkyl- sulfinyl, Ci-Cg-haloalkylsulfinyl, Ci-Cg-alkylsulfonyl, Ci-Cg-haloalkylsulfonyl;
oderor
zwei Reste R9 , die am gleichen Kohlenstoff gebunden sind, bilden gemeinsam mit diesem Kohlenstoff eine Carbonylgruppe aus;two radicals R 9 which are bonded to the same carbon form a carbonyl group together with this carbon;
oderor
zwei Reste R9 , die an verschiedenen Kohlenstoffen gebunden sind, bilden gemeinsam eine - (CH2)n~Kette, die durch einen bis drei Reste aus folgender Gruppe substituiert sein kann:two R 9 radicals which are bonded to different carbons together form a - (CH 2 ) n ~ chain, which can be substituted by one to three radicals from the following group:
Halogen, Cχ-Cg -Alkyl, Ci-Cg -Alkoxy, Hydroxy oder Ci-Cg -Alkoxycarbonyl ;Halogen, Cχ-Cg alkyl, Ci-Cg alkoxy, hydroxy or Ci-Cg alkoxycarbonyl;
R10 Cι-C6-Alkyl, C3-C6-Alkenyl, C3-Cg-Halogenalkenyl , C -Cg-Alkinyl, C3-Cg-Halogenalkinyl, C3-Cg-Cycloalkyl,R 10 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -Cg haloalkenyl, C -Cg alkynyl, C 3 -Cg haloalkynyl, C 3 -Cg cycloalkyl,
Cι-C2o-Alkylcarbonyl, C -Cg-Alkenylcarbonyl, C -Cg-Alki- nylcarbonyl, C -Cg-Cycloalkylcarbonyl, Ci-Cg-Alkoxy- carbonyl, C3-Cg-Alkenyloxycarbonyl, C -Cg-Alkinyloxy- carbonyl, Ci-Cg-Alkylthiocarbonyl, Ci-Cg-Alkylamino- carbonyl, C -Cg-Alkenylaminocarbonyl, C3-Cg-Alkinylami- nocarbonyl, N,N-Di- (Cι~Cg-alkyl) -aminocarbonyl, N- (C3-Cg-Alkenyl) -N- (Ci-Cg-alkyl) -aminocarbonyl, N- (C3-Cg-Alkinyl) -N- (Ci-Cg-alkyl) -aminocarbonyl, N- (Ci-Cg-Alkoxy) -N- (Ci-Cg-alkyl) -aminocarbonyl, N- (C3-Cg-Alkenyl) -N- (Cι~Cg-alkoxy) -aminocarbonyl,C 1 -C 2 -alkylcarbonyl, C -Cg-alkenylcarbonyl, C-Cg-alkynylcarbonyl, C-Cg-cycloalkylcarbonyl, Ci-Cg-alkoxycarbonyl, C 3 -Cg-alkenyloxycarbonyl, C -Cg-alkynyloxycarbonyl , Ci-Cg-alkylthiocarbonyl, Ci-Cg-alkylamino-carbonyl, C -Cg-alkenylaminocarbonyl, C 3 -Cg-alkynylaminocarbonyl, N, N-di- (Cι ~ Cg-alkyl) -aminocarbonyl, N- (C 3 -Cg-alkenyl) -N- (Ci-Cg-alkyl) -aminocarbonyl, N- (C 3 -Cg-alkynyl) -N- (Ci-Cg-alkyl) -aminocarbonyl, N- (Ci-Cg-alkoxy ) -N- (Ci-Cg-alkyl) -aminocarbonyl, N- (C 3 -Cg-alkenyl) -N- (-Cι ~ Cg-alkoxy) -aminocarbonyl,
N- (C3-Cg-Alkinyl) -N- (Ci-Cg-alkoxy) -aminocarbonyl, Di- (Ci-Cg-alkyl) -aminothiocarbonyl, Ci-Cg-Alkylcarbo- nyl-Ci-Cg-alkyl, Cι-Cg-Alkoxyimino-Cι-Cg-alkyl, N- (Ci-Cg-Alkylamino) -imino-Ci-Cg-alkyl oder N,N-Di- (Ci-Cg-alkylamino) -imino-Ci-Cg-alkyl, wobei die genannten Alkyl-, Cycloalkyl- und Alkoxyreste partiell oder vollständig halogeniert sein können und/oder eine bis drei der folgenden Gruppen tragen können: Cyano, Cι-C4-Alkoxy, Cι-C4-Alkylthio, Di- (Cι-C4-alkyl) - amino, Cι-C4-Alkylcarbonyl, Cι-C4-Alkoxycarbonyl , Cι-C4-Alkoxy-Cι-C4-alkoxycarbonyl , Di- (Cι-C4-alkyl) - amino-Cι-C4-alkoxycarbonyl , Hydroxycarbonyl , Cι-C4-Alkylaminocarbonyl, Di- (Cι-C4~alkyl) -aminocarbonyl, Aminocarbonyl, Cι-C4-Alkylcarbonyloxy oder C3-Cg-Cycloalkyl; Phenyl, Heterocyclyl, Phenyl-Ci-Cg-alkyl, Heterocy- clyl-Ci-Cg-alkyl, Phenylcarbonyl-Ci-Cg-alkyl, Heterocy- clylcarbonyl-Ci-Cg-alkyl, Phenylcarbonyl, Heterocyclyl - carbonyl, Phenoxycarbonyl, Phenyloxythiocarbonyl, Hete- rocyclyloxycarbonyl, Heterocyclyloxythiocarbonyl,N- (C 3 -Cg-alkynyl) -N- (Ci-Cg-alkoxy) -aminocarbonyl, di- (Ci-Cg-alkyl) -aminothiocarbonyl, Ci-Cg-alkylcarbonyl-Ci-Cg-alkyl, Cι -Cg-Alkoxyimino-Cι-Cg-alkyl, N- (Ci-Cg-alkylamino) -imino-Ci-Cg-alkyl or N, N-Di- (Ci-Cg-alkylamino) -imino-Ci-Cg-alkyl , where the alkyl, cycloalkyl and alkoxy radicals mentioned can be partially or completely halogenated and / or can carry one to three of the following groups: cyano, C 4 -C 4 -alkoxy, C 1 -C 4 -alkylthio, di- (Cι- C 4 -alkyl) - amino, -C-C 4 alkylcarbonyl, -C-C 4 -alkoxycarbonyl, Cι-C 4 -alkoxy-Cι-C 4 -alkoxycarbonyl, di- (-C-C 4 -alkyl) - amino-Cι -C 4 -alkoxycarbonyl, hydroxycarbonyl, -C-C 4 -alkylaminocarbonyl, di- (-C-C 4 ~ alkyl) -aminocarbonyl, aminocarbonyl, Cι-C 4 -alkylcarbonyloxy or C 3 -Cg-cycloalkyl; Phenyl, heterocyclyl, phenyl-Ci-Cg-alkyl, heterocyclyl-Ci-Cg-alkyl, phenylcarbonyl-Ci-Cg-alkyl, heterocyclylcarbonyl-Ci-Cg-alkyl, phenylcarbonyl, heterocyclyl - carbonyl, phenoxycarbonyl, phenyloxythiocarbonyl, Heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl,
Phenylaminocarbonyl, N- (Ci-Cg-Alkyl) -N- (phenyl) -aminocarbonyl, Heterocyclylaminocarbonyl, N- (Ci-Cg-Alkyl) - N- (heterocyclyl) -aminocarbonyl , Phenyl-C -C6-alkenyl - carbonyl oder Heterocyclyl-C2-Cg-alkenylcarbonyl, wobei der Phenyl- und der Heterocyclyl-Rest der 18 letztgenannten Substituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, Cι-C4-Alkyl, Cι-C4-Halogenalkyl, Cι-C4~Alkoxy oder Cι-C4~Halogenalkoxy;Phenylaminocarbonyl, N- (Ci-Cg-Alkyl) -N- (phenyl) -aminocarbonyl, Heterocyclylaminocarbonyl, N- (Ci-Cg-Alkyl) - N- (heterocyclyl) -aminocarbonyl, Phenyl-C -C 6 -alkenyl - carbonyl or heterocyclyl-C 2 -Cg-alkenylcarbonyl, where the phenyl and heterocyclyl radicals of the last 18 substituents can be partially or completely halogenated and / or can carry one to three of the following radicals: nitro, cyano, C 1 -C 4 - Alkyl, -CC 4 -haloalkyl, -C-C 4 ~ alkoxy or -C-C 4 ~ haloalkoxy;
R11, R12 Ci-Cg-Alkyl, C3-Cg-Alkenyl, C3-Cg-Halogenalkenyl,R 11 , R 12 Ci-Cg-alkyl, C 3 -Cg-alkenyl, C 3 -Cg-haloalkenyl,
C3-Cg-Alkinyl, C3-Cg-Halogenalkinyl , C3-C6-Cycloalkyl , Hydroxy, Ci-Cg-Alkoxy, Amino, Ci-Cg-Alkylamino, Ci-Cg-Halogenalkylamino, Di- (Ci-Cg-alkyl) amino,C 3 -Cg alkynyl, C 3 -Cg haloalkynyl, C 3 -C 6 cycloalkyl, hydroxy, Ci-Cg-alkoxy, amino, Ci-Cg-alkylamino, Ci-Cg-haloalkylamino, di- (Ci-Cg alkyl) amino,
Di- (Ci-Cg-Halogenalkyl) amino, wobei die genannten Alkyl-, Cycloalkyl- und Alkoxyreste partiell oder vollständig halogeniert sein können und/oder eine bis drei der folgenden Gruppen tragen können: Cyano, Cι-C4-Alkoxy, Cι-C4-Alkylthio, Di- (Cι-C4-alkyl) - amino, Cι-C4-Alkylcarbonyl, Cι-C4-Alkoxycarbonyl, Cι-C4-Alkoxy-Cι-C4-alkoxycarbonyl , Di- (Cι~C4-alkyl) -ami - no-Cι-C4-alkoxycarbonyl, Hydroxycarbonyl , Cι-C4~Alkyl- aminocarbonyl , Di- (C -C4-alkyl) -aminocarbonyl, Amino- carbonyl, Cι-C4-Alkylcarbonyloxy oder C3-Cg-Cycloalkyl;Di- (Ci-Cg-haloalkyl) amino, where the alkyl, cycloalkyl and alkoxy radicals mentioned can be partially or completely halogenated and / or can carry one to three of the following groups: cyano, C 1 -C 4 -alkoxy, Cι- C 4 -Alkylthio, di- (-C 4 -alkyl) - amino, -C-C 4 -alkylcarbonyl, Cι-C 4 -alkoxycarbonyl, Cι-C 4 -alkoxy-Cι-C 4 -alkoxycarbonyl, di- (Cι ~ C 4 -alkyl) -ami - no -C-C 4 alkoxycarbonyl, hydroxycarbonyl, -C-C 4 ~ alkyl-aminocarbonyl, di- (C -C 4 -alkyl) -aminocarbonyl, aminocarbonyl, Cι-C 4 -Alkylcarbonyloxy or C 3 -Cg cycloalkyl;
Phenyl, Heterocyclyl, Phenyl-Ci-Cg-alkyl, Heterocy- clyl-Ci-Cg-alkyl, Phenoxy, Heterocyclyloxy, wobei der Phenyl- und der Heterocyclyl-Rest der letztgenannten Substituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann:Phenyl, heterocyclyl, phenyl-Ci-Cg-alkyl, heterocyclyl-Ci-Cg-alkyl, phenoxy, heterocyclyloxy, where the phenyl and the heterocyclyl radical of the latter substituents can be partially or completely halogenated and / or one to three of the following leftovers:
Nitro, Cyano, Cι-C4-Alkyl, Cι-C4-Halogenalkyl, Cι-C4-Alkoxy oder Cι-C4-Halogenalkoxy;Nitro, cyano, C 4 -alkyl, C 4 haloalkyl, Cι-C 4 alkoxy or Cι-C 4 haloalkoxy;
R13 Ci - Cg -Alkyl , C3 - Cg -Alkenyl , C3 - Cg - Halogenalkenyl ,R 13 Ci - Cg alkyl, C 3 - Cg alkenyl, C 3 - Cg - haloalkenyl,
C3 -Cg -Alkinyl , C3 - Cg - Halogenalkinyl , C3 - Cg - Cycloalkyl , Hydroxy, Ci - Cg -Alkoxy, C3 - Cg -Alkenyloxy, C3 - Cg -Alkinyl - oxy, Amino , Ci - Cg -Alkylamino , Di - (Ci - Cg -Alkyl ) - amino oder Ci - Cg -Alkylcarbonylamino , wobei die genannten Alkyl-, Cycloalkyl- und Alkoxyreste partiell oder vollständig halogeniert sein können und/oder einen bis drei Reste der folgenden Gruppe tragen können: Cyano, Cι-C -Alkoxy, C1-C4 -Alkylthio, Di - (Cι-C4-alkyl) - amino, Cι-C4-Alkylcarbonyl , C1-C4 -Alkoxycarbonyl, Ci -C4-Alkoxy-C1-C4 -alkoxycarbonyl, Di- (Ci -C4 -alkyl) -amino-C1-C4-alkoxycarbonyl , Hydroxycarbonyl , Ci-C4-Alkyl - aminocarbonyl, Di- (C1-C4-alkyl) -aminocarbonyl, Aminocarbonyl, Cι-C4-Alkylcarbonyloxy oder C3 -Cg -Cycloalkyl;C 3 -Cg alkynyl, C 3 - Cg - haloalkynyl, C 3 - Cg - cycloalkyl, hydroxy, Ci - Cg -alkoxy, C 3 - Cg -alkenyloxy, C 3 - Cg -alkynyloxy-oxy, amino, Ci - Cg -Alkylamino, Di - (Ci - Cg -Alkyl) - amino or Ci - Cg -Alkylcarbonylamino, where the said Alkyl, cycloalkyl and alkoxy radicals can be partially or completely halogenated and / or can carry one to three radicals from the following group: cyano, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, di - (C 1 -C 4 - alkyl) - amino, -CC 4 alkylcarbonyl, C 1 -C 4 alkoxycarbonyl, Ci -C 4 alkoxy-C 1 -C 4 alkoxycarbonyl, di- (Ci -C 4 alkyl) amino-C 1 -C 4 alkoxycarbonyl, hydroxycarbonyl, Ci-C 4 alkyl aminocarbonyl, di (C 1 -C 4 alkyl) aminocarbonyl, aminocarbonyl, C 1 -C 4 alkylcarbonyloxy or C 3 -Cg cycloalkyl;
Phenyl, Heterocyclyl, Phenyl -Ci-Cg- alkyl oder Heterocyclyl -Ci-Cg -alkyl , wobei der Phenyl- oder Heterocyclyl-Rest der vier letztgenannten Substituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann:Phenyl, heterocyclyl, phenyl -Ci-Cg-alkyl or heterocyclyl -Ci-Cg -alkyl, where the phenyl or heterocyclyl radical of the four last-mentioned substituents can be partially or completely halogenated and / or can carry one to three of the following radicals:
Nitro, Cyano, C -C4-Alkyl, Ci -C4 -Halogenalkyl, C1-C4-Alkoxy oder C1-C4 -Halogenalkoxy;Nitro, cyano, C -C 4 alkyl, Ci -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy;
Ri Ci-Cg -Alkyl, C3-Cg-Alkenyl, C3 -C6-Alkinyl oder Ci-Cg-Alkylcarbonyl;Ri Ci-Cg alkyl, C 3 -Cg alkenyl, C 3 -C 6 alkynyl or Ci-Cg alkylcarbonyl;
q 0 bis 6q 0 to 6
sowie deren landwirtschaftlich brauchbaren Salze.and their agriculturally useful salts.
Außerdem betrifft die Erfindung Verfahren zur Herstellung von Verbindungen der Formel I, Mittel welche diese enthalten sowie die Verwendung dieser Derivate oder diese enthaltende Mittel zur Schadpflanzenbekämpfung.The invention also relates to processes for the preparation of compounds of the formula I, compositions which contain them and the use of these derivatives or compositions containing them for controlling harmful plants.
Aus der Literatur, beispielsweise aus DE-A 19 532 311 und WO 97/08164 sind Dioxothiochroman-Derivate, die mit einem gegebenenfalls substituierten (1 -Hydroxy- 3 -oxo-cyclohex-l-en-2-yl) car- bonyl-Rest verknüpft sind, bekannt. Die herbiziden Eigenschaften der bisher bekannten Verbindungen sowie die Verträglichkeiten gegenüber Kulturpflanzen können jedoch nur bedingt befriedigen. Es lag daher dieser Erfindung die Aufgabe zugrunde, neue, biologisch, insbesondere herbizid wirksame, Verbindungen mit verbesserten Eigenschaften zu finden.From the literature, for example from DE-A 19 532 311 and WO 97/08164, there are dioxothiochroman derivatives which are substituted with an optionally substituted (1-hydroxy-3-oxo-cyclohex-l-en-2-yl) carbonyl Rest are known. However, the herbicidal properties of the compounds known hitherto and the tolerances to crop plants can only satisfy to a limited extent. It was therefore the object of this invention to find new, biologically, in particular herbicidally active, compounds with improved properties.
Demgemäß wurden die Cyclohexenondioxothiochromanoyl-Derivate der Formel I sowie deren herbizide Wirkung gefunden.Accordingly, the cyclohexenone dioxothiochromanoyl derivatives of the formula I and their herbicidal activity have been found.
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. Processes for the preparation of these agents and processes for Control of undesired plant growth with the compounds I found.
Die Verbindungen der Formel I können je nach Substitutionsmuster ein oder mehrere Chiralitatszentren enthalten und liegen dann als Enantiomeren oder Diastereomerengemische vor. Gegenstand der Erfindung 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 chiral centers and are then present as enantiomers or diastereomer mixtures. 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 die Salze derjenigen Kationen oder die Säureadditionssalze derjenigen Säuren in Betracht, deren Kationen, beziehungsweise Anionen, die herbizide Wirkung der Verbindungen I nicht negativ beeinträchtigen.The compounds of the formula I can also be present in the form of their agriculturally useful salts, the type of salt generally not being important. In general, the salts of those cations or the acid addition salts of those acids whose cations or anions 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 Cι-C4-Alkyl, Hydroxy-Cι-C4-alkyl , Ci-C4 -Alkoxy-C1-C4- alkyl, Hydro- xy-Ci-C4 -alkoxy-C1-C4-alkyl, Phenyl oder Benzyl ersetzt sein kön- nen, vorzugsweise Ammonium, Dimethylammonium, Diisopropylammoni- um, Tetramethylammonium, Tetrabutylammonium, 2 - (2 -Hydroxyeth-1- oxy) eth-1-ylammonium, Di (2-hydroxyeth-l-yl) ammonium, Trimethyl- benzylammonium, des weiteren Phosphoniumionen, Sulfoniumionen, vorzugsweise Tri (Cι-C4-alkyl) sulfonium und Sulfoxoniumionen, vorzugsweise Tri (Cι-C4-alkyl) sulfoxonium, in Betracht.The cations used are, in particular, ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium and magnesium, and of the transition metals, preferably manganese, copper, zinc and iron, and ammonium, where if desired one to four hydrogen atoms by Cι- C 4 alkyl, hydroxy -CC 4 alkyl, Ci-C 4 alkoxy-C 1 -C 4 alkyl, hydroxy-Ci-C 4 alkoxy-C 1 -C 4 alkyl, phenyl or Benzyl can be replaced, preferably ammonium, dimethylammonium, diisopropylammonium, tetramethylammonium, tetrabutylammonium, 2 - (2-hydroxyeth-1-oxy) eth-1-ylammonium, di (2-hydroxyeth-l-yl) ammonium, trimethyl - Benzylammonium, further phosphonium ions, sulfonium ions, preferably tri (-C 4 alkyl) sulfonium and sulfoxonium ions, preferably tri (-C 4 alkyl) sulfoxonium, into consideration.
Anionen von brauchbaren Säureadditionsalzen sind in erster Linie Chlorid, Bromid, Fluorid, Hydrogensulfat, Sulfat, Dihydrogen- phosphat, Hydrogenphosphat, Nitrat, Hydrogencarbonat, Carbonat, Hexafluorosilikat, Hexafluorophosphat, Benzoat sowie die Anionen von Cι-C4-Alkansäuren, vorzugsweise Formiat, Acetat, Propionat und Butyrat.Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of C 1 -C 4 -alkanoic acids, preferably formate, acylate , Propionate and butyrate.
Die für die Substituenten Ri-R14 oder als Reste an Phenyl- und Heterocyclyl-Resten genannten organischen Molekülteile stellen Sammelbegriffe für individuelle Aufzählungen der einzelnen Gruppenmitglieder dar. Sämtliche Kohlenwasserstoffketten, also alle Alkyl-, Halogenalkyl-, Alkoxy-, Halogenalkoxy-, Alkylthio-, Halogenalkylthio-, Alkylsulfinyl-, Halogenalkylsulfinyl-, Alkyl - sulfonyl-, Halogenalkylsulfonyl-, N-Alkylaminosulfonyl- , N,N- Dialkylaminosulfonyl- , N-Alkylamino- , N,N-Dialkylamino- , N-Halo- genalkylamino- , N-Alkoxyamino- , N-Alkoxy-N-alkylamino- , N-Alkyl- carbonylamino- , N-Alkylsulfonylamino- , N-Halogenalkylsulfonyla- mino- , N-Alkyl-N-alkylsulfonylamino- , N-Alkyl-N-halogenalkylsul - fonylamino-, Alkylcarbonyl-, Halogenalkylcarbonyl-, Alkoxycarbonyl-, Halogenalkoxycarbonyl- , Alkylthiocarbonyl- , Alkyl - carbonyloxy- , Alkylaminocarbonyl-, Dialkylaminocarbonyl-, Dial- kylaminothiocarbonyl - , Alkoxyalkyl-, Dialkoxymethyl- , Dialkyl- thiomethyl-, (Alkoxy) (alkylthio) methyl - , Alkylcarbonylalkyl- , Alkoxyiminoalkyl - , N- (Alkylamino) -iminoalkyl - , N- (Dialkyl - amino) -iminoalkyl - , Phenylalkenylcarbonyl - , Heterocyclylalkenyl - carbonyl-, N-Alkoxy-N-alkylaminocarbonyl-, N-Alkyl-N-phenylaminocarbonyl-, N-Alkyl-N-heterocyclylaminocarbonyl-, Phenylalkyl-, Heterocyclylalkyl- , Phenylcarbonylalkyl- , Heterocyclylcarbonylal - kyl-, Dialkylaminoalkoxycarbonyl-, Alkoxyalkoxycarbonyl-, Alkenylcarbonyl-, Alkenyloxycarbonyl-, Alkenylaminocarbonyl-, N- Alkenyl-N-alkylaminocarbonyl- , N-Alkenyl-N-alkoxyaminocarbonyl-, Alkinylcarbonyl-, Alkinyloxycarbonyl-, Alkinylaminocarbonyl-, N- Alkinyl-N-alkylaminocarbonyl- , N-Alkinyl-N-alkoxyaminocarbonyl- , Alkenyl-, Alkinyl-, Halogenalkenyl-, Halogenalkinyl-, Alkenyloxy, Alkinyloxy und Alkoxyalkoxy-Teile können geradkettig oder ver- zweigt 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 molecule parts mentioned for the substituents R i -R 14 or as residues on phenyl and heterocyclyl residues represent collective terms for individual lists of the individual group members. All hydrocarbon chains, ie all alkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio -, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkyl - sulfonyl, haloalkylsulfonyl, N-alkylaminosulfonyl, N, N-dialkylaminosulfonyl, N-alkylamino, N, N-dialkylamino, N-haloalkylamino, N-alkoxyamino, N-alkoxy-N-alkylamino, N-alkyl carbonylamino, N-alkylsulfonylamino, N-haloalkylsulfonylamino, N-alkyl-N-alkylsulfonylamino, N-alkyl-N-haloalkylsulfonylylamino, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, alkylthiocarbonyl, Alkyl - carbonyloxy, alkylaminocarbonyl, dialkylaminocarbonyl, dialkylaminothiocarbonyl, alkoxyalkyl, dialkoxymethyl, dialkylthiomethyl, (alkoxy) (alkylthio) methyl, alkylcarbonylalkyl, alkoxyiminoalkyl,, N- (alkylamino) iminoalkyl - , N- (dialkyl-amino) -iminoalkyl -, phenylalkenylcarbonyl -, heterocyclylalkenyl - carbonyl-, N-alkoxy-N-alkylaminocarbonyl-, N-alkyl-N-phenylaminocarbonyl-, N-alkyl-N-heterocyclylaminocarbonyl-, phenylalkyl-, Heterocyclylalkyl, phenylcarbonylalkyl, heterocyclylcarbonylalkyl, dialkylaminoalkoxycarbonyl, alkoxyalkoxycarbonyl, alkenylcarbonyl, alkenyloxycarbonyl, alkenylaminocarbonyl, N-alkenyl-N-alkylaminocarbonyl, N-alkenylcarbonyl, N-alkoxycarbonyl Nyloxycarbonyl, alkynylaminocarbonyl, N-alkynyl-N-alkylaminocarbonyl, N-alkynyl-N-alkoxyaminocarbonyl, alkenyl, alkynyl, haloalkenyl, haloalkynyl, alkenyloxy, alkynyloxy and alkoxyalkoxy 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:
Cι-C4-Alkyl: z.B. Methyl, Ethyl, Propyl, 1-Methylethyl , Butyl, 1-Methylpropyl, 2-Methylpropyl oder 1, 1-Dirnethylethyl ;C 1 -C 4 alkyl: for example methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl or 1, 1-dimethylethyl;
- Ci-Cg-Alkyl, sowie die Alkylteile von Cι-Cg-Alkoxyimino-Cι-Cg- alkyl, N- (Ci-Cg-Alkylamino) -imino-Ci-Cg-alkyl , N- (Di-Ci-Cg- alkylamino) -imino-Ci-Cg-alkyl , N (Ci-Cg-Alkoxy) -N- (Ci-Cg- alkyl) -aminocarbonyl, N- (C3-Cg-Alkenyl) -N- (Ci-Cg-alkyl) -aminocarbonyl, (C3-Cg-Alkinyl) -N- (Ci-Cg-alkyl) -aminocarbonyl, N- (Ci-Cg-Alkyl) -N-phenylaminocarbonyl, N- (Ci-Cg-Alkyl) -N- heterocyclylaminocarbonyl, Phenyl-Ci-Cg-alkyl, N- (Ci-Cg- Alkyl) -N- (Ci-Cg-alkylsulfonyl) -amino, N- (Ci-Cg-Alkyl) -N- (Ci-Cg-halogenalkylsulfonyl) -amino, Heterocyclyl-Ci-Cg-alkyl, Phenylcarbonyl-Ci-Cg-alkyl , Heterocyclylcarbonyl-Ci-Cg-alkyl : Cι-C4-Alkyl, wie voranstehend genannt, sowie z.B. Pentyl, 1-Methylbutyl, 2-Methylbutyl , 3-Methylbutyl , 2, 2-Dimethyl- propyl, 1-Ethylpropyl, Hexyl, 1, 1-Dimethylpropyl, 1,2-Dime- thylpropyl, 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 oder 1-Ethyl-3-methyl - propyl ;- Ci-Cg-alkyl, as well as the alkyl parts of -C-Cg-alkoxyimino-Cι-Cg-alkyl, N- (Ci-Cg-alkylamino) -imino-Ci-Cg-alkyl, N- (di-Ci-Cg- alkylamino) imino-Ci-Cg-alkyl, N (Ci-Cg-alkoxy) -N- (Ci-Cg-alkyl) aminocarbonyl, N- (C 3 -Cg-alkenyl) -N- (Ci-Cg- alkyl) -aminocarbonyl, (C 3 -Cg-alkynyl) -N- (Ci-Cg-alkyl) -aminocarbonyl, N- (Ci-Cg-alkyl) -N-phenylaminocarbonyl, N- (Ci-Cg-alkyl) - N- heterocyclylaminocarbonyl, phenyl-Ci-Cg-alkyl, N- (Ci-Cg-alkyl) -N- (Ci-Cg-alkylsulfonyl) -amino, N- (Ci-Cg-alkyl) -N- (Ci-Cg haloalkylsulfonyl) amino, heterocyclyl-Ci-Cg-alkyl, phenylcarbonyl-Ci-Cg-alkyl, heterocyclylcarbonyl-Ci-Cg-alkyl: -C-C 4 alkyl, as mentioned above, and for example pentyl, 1-methylbutyl, 2nd -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-di methylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-tri- methylpropyl, 1-ethyl-l-methylpropyl or 1-ethyl-3-methylpropyl;
Cι~C4-Halogenalkyl : einen Cι-C4-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, Pentafluorethyl, 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,Cι ~ C 4 -haloalkyl: a Cι-C4 alkyl group such as overall Nannt above which is partially or fully substituted by fluorine, chlorine, bromine and / or iodine, eg chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, Trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorofluoromethyl, 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, 2- 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;
Ci-Cg-Halogenalkyl, sowie die Halogenalkylteile von N-C -Cg-Halogenalkylamino: Cι-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;Ci-Cg-haloalkyl, and the haloalkyl parts of NC -Cg-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;
Cι~C4-Alkoxy: z.B. Methoxy, Ethoxy, Propoxy, 1-Methylethoxy, Butoxy, 1-Methylpropoxy, 2-Methylpropoxy oder 1, 1-Dimethyl- ethoxy;Cι ~ C 4 alkoxy: eg methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1, 1-dimethylethoxy;
Ci-Cg-Alkoxy, sowie die Alkoxyteile von N-Ci-Cg-Alkoxyamino, Di- (Ci-Cg-alkoxy) methyl, (Ci-Cg-Alkoxy) (Ci-Cg-alkylthio) - methyl, Cι-Cg-Alkoxyimino-Cι-Cg-alkyl, N- (Ci-Cg-Alkoxy) -N- (Ci-Cg-alkyl) -aminocarbonyl, N- (C3-Cg-Alkenyl) -N- (Ci-Cg-alk- oxy) -aminocarbonyl und N- (C3-Cg-Alkinyl) -N- (Cι~Cg-alkoxy) - aminocarbonyl: Cι-C4-Alkoxy, wie voranstehend genannt, sowie z.B. Pentoxy, 1-Methylbutoxy, 2-Methylbutoxy, 3-Methylbutoxy, 1, 1-Dimethylpropoxy, 1, 2-Dimethylpropoxy, 2 , 2-Dimethylprop- oxy, 1-Ethylpropoxy, Hexoxy, 1-Methylpentoxy, 2-Methyl- pentoxy, 3-Methylpentoxy, 4-Methylpentoxy, 1, 1-Dimethyl- butoxy, 1, 2-Dimethylbutoxy, 1, 3-Dimethylbutoxy, 2, 2-Dimethyl- butoxy, 2 , 3-Dimethylbutoxy, 3 , 3-Dimethylbutoxy, 1-Ethyl- butoxy, 2-Ethylbutoxy, 1, 1, 2-Trimethylpropoxy, 1,2,2-Tri- methylpropoxy, 1-Ethyl-l-methylpropoxy oder l-Ethyl-2-methyl- propoxy; Cι-C4-Halogenalkoxy: einen Cι-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-Iodethoxy, 2 , 2-Difluorethoxy, 2 , 2 , 2-Trifluorethoxy, 2-Chlor-2-fluorethoxy, 2-Chlor-2, 2-difluorethoxy, 2,2-Di- chlor-2-fluorethoxy, 2 , 2 , 2-Trichlorethoxy, Pentafluorethoxy, 2-Fluorpropoxy, 3-Fluorpropoxy, 2-Chlorpropoxy, 3-Chlor- propoxy, 2-Brompropoxy, 3-Brompropoxy, 2, 2-Difluorpropoxy,Ci-Cg-alkoxy, and the alkoxy parts of N-Ci-Cg-alkoxyamino, di- (Ci-Cg-alkoxy) methyl, (Ci-Cg-alkoxy) (Ci-Cg-alkylthio) - methyl, Cι-Cg- Alkoxyimino-Cι-Cg-alkyl, N- (Ci-Cg-alkoxy) -N- (Ci-Cg-alkyl) -aminocarbonyl, N- (C 3 -Cg-alkenyl) -N- (Ci-Cg-alk- oxy) -aminocarbonyl and N- (C 3 -Cg-alkynyl) -N- (Cι ~ Cg-alkoxy) - aminocarbonyl: Cι-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-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1st , 1-dimethylbutoxy, 1, 2-dimethylbutoxy, 1, 3-dimethylbutoxy, 2, 2-dimethylbutoxy, 2, 3-dimethylbutoxy, 3, 3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1 , 1, 2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-l-methylpropoxy or l-ethyl-2-methylpropoxy; Cι-C 4 -haloalkoxy: a Cι-C4-alkoxy as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and / or iodine, ie, for example fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, Bromdi- 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- Difluoropropoxy,
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;2, 3-difluoropropoxy, 2, 3-dichloropropoxy, 3, 3, 3-trifluoropropoxy, 3, 3, 3-trichloropropoxy, 2, 2, 3, 3, 3-pentafluoropropoxy, heptafluoropropoxy, 1- (fluoromethyl) -2- fluoroethoxy, 1- (chloromethyl) -2-chloroethoxy, 1- (bromomethyl) -2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy;
Ci-Cg-Halogenalkoxy: Cι-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;Ci-Cg-haloalkoxy: Cι-C4-haloalkoxy, as mentioned above, and e.g. 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy;
Cι-C4-Alkylthio: z.B. Methylthio, Ethylthio, Propylthio, 1-Methylethylthio, Butylthio, 1-Methylpropylthio, 2-Methyl- propylthio oder 1, 1-Dimethylethylthio;C 1 -C 4 -Alkylthio: for example methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio or 1, 1-dimethylethylthio;
Ci-Cg-Alkylthio, sowie die Alkylthioteile von Ci-Cg-Alkylthio- carbonyl, Di- (Cι-Cg-alkylthio)methyl undCi-Cg-alkylthio, and the alkylthio parts of Ci-Cg-alkylthio-carbonyl, di- (-C-Cg-alkylthio) methyl and
(Ci-Cg-Alkoxy) (Cι-Cg-alkylthio)methyl: Cι-C4-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,(Ci-Cg-alkoxy) (-C-Cg-alkylthio) methyl: -C-C 4 alkylthio, as mentioned above, and for example pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2, 2-dimethyl - propylthio, 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 oder l-Ethyl-2-methylpropylthio;3, 3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1, 2-trimethylpropylthio, 1,2, 2-trimethylpropylthio, 1-ethyl-l-methylpropylthio or l-ethyl-2-methylpropylthio;
Cι-C4~Halogenalkylthio: einen Cι-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, 2-Chlor-2 , 2-di- fluorethylthio, 2 , 2-Dichlor-2-fluorethylthio, Pentafluor- ethylthio, 2-Fluorpropylthio, 3-Fluorpropylthio, 2-Chlor- propylthio, 3-Chlorpropylthio, 2-Brompropylthio, 3-Brom- propylthio, 2, 2-Difluorpropylthio, 2 , 3-Difluorpropylthio, Cι-C4 ~ haloalkylthio: a Cι-C4-alkylthio, as mentioned above, which is partially or fully substituted by fluorine, chlorine, bromine and / or iodine, eg fluorine - methylthio, difluoromethylthio, trifluoromethylthio, difluoromethylthio chlorine, 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-chloro-2, 2-di-fluoroethylthio, 2, 2-dichloro-2-fluoroethylthio, pentafluoroethylthio, 2-fluoropropylthio, 3-fluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2-bromopropylthio, 3-bromopropylthio, 2, 2-difluoropropylthio, 2, 3-difluoropropylthio,
2, 3-Dichlorpropylthio, 3 , 3 , 3-Trifluorpropylthio, 3,3,3-Trich- lorpropylthio, 2, 2, 3, 3 , 3-Pentafluorpropylthio, Heptafluor- propylthio, 1- (Fluormethyl) -2-fluorethylthio, 1- (Chlormethyl) -2-chlorethylthio, 1- (Brommethyl) -2-bromethylthio, 4-Fluorbutylthio, 4-Chlorbutylthio, 4-Brombutylthio oder Nonafluorbutylthio;2, 3-dichloropropylthio, 3, 3, 3-trifluoropropylthio, 3,3,3-trichloropropylthio, 2, 2, 3, 3, 3-pentafluoropropylthio, heptafluoropropylthio, 1- (fluoromethyl) -2-fluoroethylthio, 1- (chloromethyl) -2-chloroethylthio, 1- (bromomethyl) -2-bromethylthio, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio or nonafluorobutylthio;
Ci-Cg-Halogenalkylthio: Cι-C4-Halogenalkylthio, wie voranstehend genannt, sowie z.B. 5-Fluorpentylthio, 5-Chlorpen- tylthio, 5-Brompe tylthio, 5-Iodpentylthio, Undecafluorpen- tylthio, 6-Fluorhexylthio, 6-Chlorhexylthio, 6-Bromhexylthio, 6-Iodhexylthio oder Dodecafluorhexylthio;Ci-Cg-haloalkylthio: -C-C 4 -haloalkylthio, as mentioned above, and, for example, 5-fluoropentylthio, 5-chloropentylthio, 5-bromotylthio, 5-iodopentylthio, undecafluoropentylthio, 6-fluorhexylthio, 6-chlorohexylthio, 6-bromohexylthio, 6-iodohexylthio or dodecafluorohexylthio;
Ci-Cg-Alkylsulfinyl (Ci-Cg-Alkyl-S (=0) -) : z.B. Methylsulfinyl , Ethylsulfinyl, Propylsulfinyl, 1-Methylethylsulfinyl, Butyl- sulfinyl, 1-Methylpropylsulfinyl, 2-Methylpropylsulfinyl, 1, 1-Dimethylethylsulfinyl, Pentylsulfinyl, 1-Methylbutylsul- finyl, 2-Methylbutylsulfinyl, 3-Methylbutylsulfinyl, 2,2-Di- methylpropylsulfinyl, 1-Ethylpropylsulfinyl, 1, 1-Dimethylpro- pylsulfinyl, 1, 2-Dimethylpropylsulfinyl, Hexylsulfinyl,Ci-Cg-alkylsulfinyl (Ci-Cg-alkyl-S (= 0) -): e.g. Methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1, 1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfylsulfyl methylpropylsulfinyl, 1-ethylpropylsulfinyl, 1, 1-dimethylpropylsulfinyl, 1, 2-dimethylpropylsulfinyl, hexylsulfinyl,
1-Methylpentylsulfinyl, 2-Methylpentylsulfinyl, 3-Methylpen- tylsulfinyl, 4-Methylpentylsulfinyl, 1, 1-Dimethylbutylsulfi- nyl, 1, 2-Dimethylbutylsulfinyl, 1, 3-Dimethylbutylsulfinyl, 2 , 2-Dimethylbutylsulfinyl, 2, 3-Dimethylbutylsulfinyl, 3,3-Di- methylbutylsulfinyl, 1-Ethylbutylsulfinyl, 2-Ethylbutylsulfi - nyl, 1, 1, 2-Trimethylpropylsulfinyl, 1, 2 , 2-Trimethylpropylsul - finyl, 1-Ethyl-l-methylpropylsulfinyl oder l-Ethyl-2-methyl- propy1sulfinyl;1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1, 1-dimethylbutylsulfinyl, 1, 2-dimethylbutylsulfinyl, 1, 3-dimethylbutylsulfinyl, 2, 2-dimethylbutylsulfinyl, 2, 3-dimethyl 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1, 1, 2-trimethylpropylsulfinyl, 1, 2, 2-trimethylpropylsulfonyl, 1-ethyl-l-methylpropylsulfinyl or l-ethyl-2- methyl propyl sulfinyl;
Ci-Cg-Halogenalkylsulfinyl : ein Ci-Cg-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 , 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-Difluor- propylsulfinyl, 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, Nona- fluorbutylsulfinyl, 5-Fluorpentylsulfinyl, 5-Chlorpentylsul- finyl, 5-Brompentylsulfinyl, 5-Iodpentylsulfinyl, Undeca- fluorpentylsulfinyl, 6-Fluorhexylsulfinyl, 6-Chlorhexyl- sulfinyl, 6-Bromhexylsulfinyl, 6-Iodhexylsulfinyl oder Dodecafluorhexylsulfinyl;Ci-Cg-haloalkylsulfinyl: a Ci-Cg-alkylsulfinyl radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example fluoromethylsulfinyl, difluoromethylsulfinyl, trifluoromethylsulfinyl, chlorodifluoromethylsulfinyl, bromodifluoromethylsulfonyl 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, 2, 2-dichloro-2-fluoroethylsulfinyl, pentafluoromethylsulfinyl, 2-fluoropropylsulfinyl, 3-fluoropropylsulfinyl, 2-chloropropylsulfinyl, 3-chloropropylsulfinyl, 2-bromopropylsulfinyl, 3-bromopropylsulfinyl, 3-bromopropylsulfinyl 2,2-difluoropropylsulfinyl, 2,3-difluoro propylsulfinyl, 2, 3-dichloropropylsulfinyl, 3, 3, 3-trifluoropropylsulfinyl, 3, 3, 3-trichloropropylsulfinyl, 2, 2, 3, 3, 3-pentafluoropropylsulfinyl, heptafluoropropylsulfinyl, 1- (fluoromethyl) -2- fluoroethylsulfinyl, 1- (chloromethyl) -2-chloroethylsulfinyl, 1- (bromomethyl) -2-bromomethylsulfinyl, 4-fluorobutylsulfinyl, 4-chlorobutylsulfinyl, 4-bromobutylsulfinyl, non-fluorobutylsulfinyl, 5-fluoropentylsulfinyl, 5-chloropentylsulfinyl finyl, 5-bromopentylsulfinyl, 5-iodopentylsulfinyl, undecafluoropentylsulfinyl, 6-fluorohexylsulfinyl, 6-chlorohexylsulfinyl, 6-bromohexylsulfinyl, 6-iodohexylsulfinyl or dodecafluorohexylsulfinyl;
Ci-Cg-Alkylsulfonyl (Ci-Cg-Alkyl-S (=0) 2-) , sowie die Alkyl - sulfonylreste von N- (Ci-Cg-Alkylsulfonyl) -amino und N- (Cι~Cg- Alkyl) -N- (Ci-Cg-alkylsulfonyl) -amino: z.B. Methylsulfonyl ,Ci-Cg-alkylsulfonyl (Ci-Cg-alkyl-S (= 0) 2 -), as well as the alkyl - sulfonyl residues of N- (Ci-Cg-alkylsulfonyl) amino and N- (Cι ~ Cg-alkyl) -N - (Ci-Cg-alkylsulfonyl) amino: for example methylsulfonyl,
Ethylsulfonyl, Propylsulfonyl , 1-Methylethylsulfonyl, Butyl - sulfonyl, 1-Methylpropylsulfonyl, 2-Methylpropylsulfonyl, 1, 1-Dimethylethylsulfonyl, Pentylsulfonyl , 1-Methylbutyl- sulfonyl, 2-Methylbutylsulfonyl, 3-Methylbutylsulfonyl, 1, 1-Dimethylpropylsulfonyl, 1, 2-Dimethylpropylsulfonyl,Ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, 1, 1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 1-methylbutylsulfonyl, 3-methylbutylsulfonyl, 3-methylbutylsulfonyl, 3-methylbutylsulfonyl, 3-methylbutylsulfonyl, 3-methylbutylsulfonyl, 3-methylbutylsulfonyl, 3-methylbutylsulfonyl, 3-methylbutylsulfonyl, 3-methylbutylsulfonyl, 3-methylbutylsulfonyl, 3-methylbutylyl, 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-Dimethylbutylsulfonyl, 2 , 3-Dimethylbutylsulfonyl, 3 , 3-Dimethylbutylsulfonyl, 1-Ethylbutylsulfonyl, 2-Ethylbutylsulfonyl , 1,1, 2-Trimethylpropylsulfonyl , 1,2, 2-Trimethylpropylsulfonyl , 1-Ethyl-l-methylpropylsulfonyl oder l-Ethyl-2-methylpropylsulfonyl ;2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1, 1-dimethylbutylsulfonyl, 1, 2-dimethylbutylsulfonyl, 1, 2-dimethylbutylsulfonyl sulfonyl, 2, 2-dimethylbutylsulfonyl, 2, 3-dimethylbutylsulfonyl, 3, 3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1, 2-trimethylpropylsulfonyl, 1,2, 2-trimethylpropylsulfonyl, 1,2 methylpropylsulfonyl or l-ethyl-2-methylpropylsulfonyl;
Ci-Cg-Halogenalkylsulfonyl, sowie die Halogenalkylreste von N- (Ci-Cg-Halogenalkylsulfonyl) -amino und N- (Ci-Cg-Alkyl) -N- (Ci-Cg-halogenalkylsulfonyl) -amino: einen Ci-Cg-Alkylsulfonyl- rest, wie voranstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder Iod substituiert ist, also z.B. Fluormethylsulfonyl, Difluormethylsulfonyl, Trifluor- methylsulfonyl, Chlordifluormethylsulfonyl, Bromdifluormethylsulfonyl, 2-Fluorethylsulfonyl, 2-Chlorethylsulfonyl, 2-Bromethylsulfonyl, 2-Iodethylsulfonyl, 2, 2-Difluorethylsul- fonyl, 2 , 2, 2-Trifluorethylsulfonyl, 2-Chlor-2-fluorethylsul- fonyl, 2-Chlor-2,2-difluorethylsulfonyl, 2 , 2-Dichlor-2-fluorethylsulfonyl , 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, 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, Nonafluorbutylsulfonyl, 5-Fluorpentylsulfonyl, 5-Chlorpenty1 - sulfonyl, 5-Brompentylsulfonyl , 5-Iodpentylsulfonyl, 6-Fluor- hexylsulfonyl, 6-Bromhexylsulfonyl, 6-Iodhexylsulfonyl oder Dodecafluorhexylsulfonyl ;Ci-Cg-haloalkylsulfonyl, and the haloalkyl radicals of N- (Ci-Cg-haloalkylsulfonyl) amino and N- (Ci-Cg-alkyl) -N- (Ci-Cg-haloalkylsulfonyl) amino: a Ci-Cg-alkylsulfonyl - The rest, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example fluoromethylsulfonyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifluoromethylsulfonyl, 2-fluoroethylsulfonyl, 2-chloroethyl-sulfonyl, 2-chloroethylsulfonyl 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, pentafluoroethylsulfonyl, 2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl, 2-chloropropylsulfonyl, 3-chloropropylsulfonyl, 2-bromopropylsulfonyl, 3-bromopropylsulfonyl, 2, 2-propylsulfonyl, 2, 2-propylsulfonyl 2, 3-dichloropropylsulfonyl, 3,3, 3-trifluoropropylsulfone yl, 3,3, 3-trichloropropylsulfonyl, 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, nonafluorobutylsulfonyl, 5-fluoropentylsulfonyl, 5-chloropentylsulfonyl, 5-bromopentylsulfonyl, 5-iodopentylsulfonyl, 6-fluoro-hexylsulfonylylodonylodonyl, 6-fluorosulfonylodonyl;
- Ci-Cg-Alkylamino, sowie die Alkylaminoreste von N- (Cι~Cg-- Ci-Cg-alkylamino, and the alkylamino residues of N- (Cι ~ Cg-
Alkylamino) -imino-Ci-Cg-alkyl, also z.B. Methylamino, Ethyl - amino, Propylamino, 1-Methylethylamino, Butylamino, 1-Methyl - propylamino, 2-Methylpropylamino, 1, 1-Dimethylethylamino, Pentylamino, 1-Methylbutylamino, 2-Methylbutylamino, 3-Methylbutylamino, 2, 2-Dimethylpropylamino, 1-Ethylpropyl- amino, Hexylamino, 1, 1-Dimethylpropylamino, 1, 2-Dimethyl- propylamino, 1-Methylpentylamino, 2-Methylpentylamino, 3-Methylpentylamino, 4-Methylpentylamino, 1, 1-Dimethylbutyl- amino, 1, 2-Dimethylbutylamino, 1, 3-Dimethylbutylamino, 2, 2-Dimethylbutylamino, 2, 3-Dimethylbutylamino, 3 , 3-Dimethyl- butylamino, 1-Ethylbutylamino, 2-Ethylbutylamino, 1,1,2-Tri- methylpropylamino, 1,2, 2-Trimethylpropylamino, 1-Ethyl-l-methylpropylamino oder l-Ethyl-2-methylpropylamino;Alkylamino) -imino-Ci-Cg-alkyl, e.g. Methylamino, ethylamino, propylamino, 1-methylethylamino, butylamino, 1-methylpropylamino, 2-methylpropylamino, 1, 1-dimethylethylamino, pentylamino, 1-methylbutylamino, 2-methylbutylamino, 3-methylbutylamino, 2, 2-dimethylpropylamino 1-ethylpropylamino, hexylamino, 1, 1-dimethylpropylamino, 1, 2-dimethylpropylamino, 1-methylpentylamino, 2-methylpentylamino, 3-methylpentylamino, 4-methylpentylamino, 1, 1-dimethylbutylamino, 1, 2- Dimethylbutylamino, 1, 3-dimethylbutylamino, 2, 2-dimethylbutylamino, 2, 3-dimethylbutylamino, 3, 3-dimethylbutylamino, 1-ethylbutylamino, 2-ethylbutylamino, 1,1,2-trimethylpropylamino, 1,2, 2-trimethylpropylamino, 1-ethyl-l-methylpropylamino or l-ethyl-2-methylpropylamino;
- (Cι-C4-Alkylamino) sulfonyl: z.B. Methylaminosulfonyl, Ethyl - aminosulfonyl, Propylaminosulfonyl , 1-Methylethylaminosulfonyl, Butylaminosulfonyl, 1-Methylpropylaminosulfonyl, 2-Methylpropylaminosulfonyl oder 1, 1-Dirnethylethylamino- sulfonyl;- (C 1 -C 4 -alkylamino) sulfonyl: for example methylaminosulfonyl, ethylaminosulfonyl, propylaminosulfonyl, 1-methylethylaminosulfonyl, butylaminosulfonyl, 1-methylpropylaminosulfonyl, 2-methylpropylaminosulfonyl or 1, 1-dirnethylethylamino sulfonyl
(Ci-Cg-Alkylamino) sulfonyl : (C1-C4-Alkylanu.no) sulfonyl, wie vorstehend genannt, sowie z.B. Pentylaminosulfonyl, 1-Methyl- butylaminosulfonyl, 2-Methylbutylaminosulfonyl, 3-Methylbuty- laminosulfonyl, 2, 2-Dimethylpropylaminosulfonyl, 1-Ethylpro- pylaminosulfonyl, Hexylaminosulfonyl, 1, 1-Dimethylpropylami- nosulfonyl, 1, 2-Dimethylpropylaminosulfonyl, 1-Methylpentyl- aminosulfonyl, 2-Methylpentylaminosulfonyl, 3-Methylpentyl - ciminosulfonyl, 4-Methylpentylaminosulfonyl, 1, 1-Dimethyl- butylaminosulfonyl, 1, 2-Dimethylbutylaminosulfonyl, 1,3-Di- methylbutylaminosulfonyl, 2 , 2-Dimethylbutylaminosulfonyl ,(Ci-Cg-alkylamino) sulfonyl: (C 1 -C 4 -alkylanu.no) sulfonyl, as mentioned above, and for example pentylaminosulfonyl, 1-methylbutylaminosulfonyl, 2-methylbutylaminosulfonyl, 3-methylbutylaminosulfonyl, 2, 2- Dimethylpropylaminosulfonyl, 1-ethylpropylaminosulfonyl, hexylaminosulfonyl, 1, 1-dimethylpropylaminosulfonyl, 1, 2-dimethylpropylaminosulfonyl, 1-methylpentylaminosulfonyl, 2-methylpentylaminosulfonyl, 3-methylpentyl, 1-methylpentyl, 1-methylpentyl, 4-methyl-4-nylsulfonyl butylaminosulfonyl, 1, 2-dimethylbutylaminosulfonyl, 1,3-dimethylbutylaminosulfonyl, 2, 2-dimethylbutylaminosulfonyl,
2 , 3-Dimethylbutylaminosulfonyl , 3 , 3-Dimethylbutylaminosulfo- nyl , 1-Ethylbutylaminosulfonyl, 2-Ethylbutylaminosulfonyl, 1,1, 2-Trimethylpropylaminosulfonyl, 1,2, 2-Trimethylpropyl - aminosulfonyl, 1-Ethyl-l-methylpropylaminosulfonyl oder l-Ethyl-2-methylpropylaminosulfonyl ; Di- (Cι-C4-alkyl) -aminosulfonyl: z.B. N, N-Dimethylaminosulfo- nyl, N,N-Diethylaminosulfonyl, N, N-Di- (1-methylethyl) aminosulfonyl, N,N-Dipropylaminosulfonyl, N, N-Dibutylaminosulfo- nyl, N, N-Di- (1-methylpropyl) -aminosulfonyl, N, N-Di- (2-methyl - propyl) -aminosulfonyl, N, N-Di- (1, 1-dimethylethyl) -aminosulfonyl, N-Ethyl-N-methylaminosulfonyl, N-Methyl-N-propyl - aminosulfonyl, N-Methyl-N- (1-methylethyl) -aminosulfonyl, N-Butyl-N-methylaminosulfonyl , N-Methyl-N- ( 1-methyl - propyl) -aminosulfonyl, N-Methyl-N- (2-methylpropyl) -amino- sulfonyl , N- (1 , 1-Dimethylethyl) -N-methylaminosulfonyl , N-Ethyl-N-propylaminosulfonyl, N-Ethyl-N- (1-methylethyl) -aminosulfonyl , N-Butyl-N-ethylaminosulfonyl, N- Ethyl-N- (1-methylpropyl) -aminosulfonyl , N-Ethyl-N- (2-methyl - propyl) -aminosulfonyl, N-Ethyl-N- (1, 1-dimethylethyl) -amino- sulfonyl, N- (1-Methylethyl) -N-propylaminosulfonyl, N-Butyl- N-propylaminosulfonyl , N- (1-Methylpropyl) -N-propylamino- sulfonyl, N- (2-Methylpropyl) -N-propylaminosulfonyl, N- (1, 1-Dimethylethyl) -N-propylaminosulfonyl , N-Butyl-N- ( 1-methylethyl) -aminosulfonyl, N- (1-Methylethyl) -N- (1-methyl - propyl) -aminosulfonyl, N- (1-Methylethyl) -N- (2-methyl - propyl) -aminosulfonyl, N- (1, 1-Dimethylethyl) -N- (1-methylethyl) -aminosulfonyl, N-Butyl-N- (1-methylpropyl) -aminosulfonyl, N-Butyl-N- (2-methylpropyl) -aminosulfonyl, N- Butyl-N- (1, 1-dimethylethyl) -aminosulfonyl, N- (1-Methyl- propyl) -N- (2-methylpropyl) -aminosulfonyl, N- (1, 1-Dimethylethyl) -N- (1-methylpropyl) -aminosulfonyl oder N- (1, 1-Dimethylethyl) -N- (2-methylpropyl) -aminosulfonyl;2, 3-dimethylbutylaminosulfonyl, 3, 3-dimethylbutylaminosulfonyl, 1-ethylbutylaminosulfonyl, 2-ethylbutylaminosulfonyl, 1,1, 2-trimethylpropylaminosulfonyl, 1,2, 2-trimethylpropylaminosulfonyl, 1-ethyl-l-methyl-1-methylpropyl Ethyl 2-methylpropylaminosulfonyl; Di- (-C-C 4 -alkyl) -aminosulfonyl: for example N, N-dimethylaminosulfonyl, N, N-diethylaminosulfonyl, N, N-di- (1-methylethyl) aminosulfonyl, N, N-dipropylaminosulfonyl, N, N -Dibutylaminosulfonyl, N, N-Di- (1-methylpropyl) -aminosulfonyl, N, N-Di- (2-methyl-propyl) -aminosulfonyl, N, N-Di- (1, 1-dimethylethyl) -aminosulfonyl , N-ethyl-N-methylaminosulfonyl, N-methyl-N-propylaminosulfonyl, N-methyl-N- (1-methylethyl) aminosulfonyl, N-butyl-N-methylaminosulfonyl, N-methyl-N- (1- methyl-propyl) -aminosulfonyl, N-methyl-N- (2-methylpropyl) -aminosulfonyl, N- (1, 1-dimethylethyl) -N-methylaminosulfonyl, N-ethyl-N-propylaminosulfonyl, N-ethyl-N - (1-Methylethyl) aminosulfonyl, N-butyl-N-ethylaminosulfonyl, N-ethyl-N- (1-methylpropyl) aminosulfonyl, N-ethyl-N- (2-methylpropyl) aminosulfonyl, N-ethyl -N- (1, 1-dimethylethyl) -aminosulfonyl, N- (1-methylethyl) -N-propylaminosulfonyl, N-butyl-N-propylaminosulfonyl, N- (1-methylpropyl) -N-propylaminosulfonyl, N - (2-methylprop yl) -N-propylaminosulfonyl, N- (1, 1-dimethylethyl) -N-propylaminosulfonyl, N-butyl-N- (1-methylethyl) -aminosulfonyl, N- (1-methylethyl) -N- (1-methyl - propyl) aminosulfonyl, N- (1-methylethyl) -N- (2-methylpropyl) aminosulfonyl, N- (1, 1-dimethylethyl) -N- (1-methylethyl) aminosulfonyl, N-butyl-N - (1-methylpropyl) aminosulfonyl, N-butyl-N- (2-methylpropyl) aminosulfonyl, N-butyl-N- (1, 1-dimethylethyl) aminosulfonyl, N- (1-methylpropyl) -N - (2-methylpropyl) aminosulfonyl, N- (1, 1-dimethylethyl) -N- (1-methylpropyl) aminosulfonyl or N- (1, 1-dimethylethyl) -N- (2-methylpropyl) aminosulfonyl;
Di- (Ci-Cg-alkyl) -aminosulfonyl : Di- (Cι-C4~alkyl) -amino- sulfonyl, wie voranstehend genannt, sowie z.B. N-Methyl- N-pentylaminosulfonyl, N-Methyl-N- (1-methylbutyl) -aminosulfonyl, N-Methyl-N- (2-methylbutyl) -aminosulfonyl, N- Methyl-N- (3-methylbutyl) -aminosulfonyl, N-Methyl-N- (2, 2-dimethylpropyl) -aminosulfonyl, N-Methyl-N- (1-ethyl- propyl) -aminosulfonyl, N-Methyl-N-hexylaminosulfonyl, N- Methyl-N- (1 , 1-dimethylpropyl) -aminosulfonyl , N-Methyl- N- (1, 2-dimethylpropyl) -aminosulfonyl, N-Methyl-N- (1-methyl - pentyl) -aminosulfonyl, N-Methyl-N- (2-methylpentyl) -aminosulfonyl, N-Methyl-N- (3-methylpentyl) -aminosulfonyl, N- Methyl-N- (4-methylpentyl) -aminosulfonyl, N-Methyl-N-Di- (Ci-Cg-alkyl) -aminosulfonyl: Di- (-C-C 4 ~ alkyl) -aminosulfonyl, as mentioned above, and for example N-methyl-N-pentylaminosulfonyl, N-methyl-N- (1- methylbutyl) -aminosulfonyl, N-methyl-N- (2-methylbutyl) -aminosulfonyl, N-methyl-N- (3-methylbutyl) -aminosulfonyl, N-methyl-N- (2,2-dimethylpropyl) -aminosulfonyl, N -Methyl-N- (1-ethyl-propyl) -aminosulfonyl, N-methyl-N-hexylaminosulfonyl, N-methyl-N- (1, 1-dimethylpropyl) -aminosulfonyl, N-methyl- N- (1, 2- dimethylpropyl) aminosulfonyl, N-methyl-N- (1-methylpentyl) aminosulfonyl, N-methyl-N- (2-methylpentyl) aminosulfonyl, N-methyl-N- (3-methylpentyl) aminosulfonyl, N - Methyl-N- (4-methylpentyl) aminosulfonyl, N-methyl-N-
(1, 1-dimethylbutyl) -aminosulfonyl, N-Methyl-N- (1, 2-dimethyl- butyl) -aminosulfonyl, N-Methyl-N- (1, 3-dimethylbutyl) -aminosulfonyl, N-Methyl-N- (2, 2-dimethylbutyl) -aminosulfonyl, N- Methyl-N- (2, 3-dimethylbutyl) -aminosulfonyl, N-Methyl-N- (3, 3-dimethylbutyl) -aminosulfonyl, N-Methyl-N- (1-ethyl- butyl) -aminosulfonyl, N-Methyl-N- (2-ethylbutyl) -aminosulfonyl, N-Methyl-N- (1, 1, 2-trimethylpropyl) -aminosulfonyl. N-Methyl-N- (1,2, 2-trimethylpropyl) -aminosulfonyl, N- Methyl-N- (1-ethyl-l-methylpropyl) -aminosulfonyl, N-Methyl-N- (l-ethyl-2-methylpropyl) -aminosulfonyl, N-Ethyl-N-pentylaminosulfonyl, N-Ethyl-N- (1-methylbutyl) -aminosulfonyl, N- Ethyl-N- (2-methylbutyl) -aminosulfonyl, N-Ethyl-N- (3-methyl - butyl) -aminosulfonyl, N-Ethyl-N- (2, 2-dimethylpropyl) -aminosulfonyl, N-Ethyl-N- (1-ethylpropyl) -aminosulfonyl, N-Ethyl- N-hexylaminosulfonyl , N-Ethyl-N- ( 1 , 1-dimethylpropyl) -amino- sulfonyl, N-Ethyl-N- (1, 2-dimethylpropyl) -aminosulfonyl, N- Ethyl-N- (1-methylpentyl) -aminosulfonyl, N-Ethyl-N- (2-methyl - pentyl) -aminosulfonyl , N-Ethyl-N- (3-methylpentyl) -amino- sulfonyl, N-Ethyl-N- (4-methylpentyl) -aminosulfonyl, N- Ethyl-N- (1, 1-dimethylbutyl) -aminosulfonyl, N- Ethyl-N- (1,2-dimethylbutyl) -aminosulfonyl, N- Ethyl-N- (1, 3-dimethylbutyl) -aminosulfonyl, N- Ethyl-N- (2, 2-dimethylbutyl) -aminosulfonyl, N- Ethyl-N- (2,3-dimethylb tyl) -aminosulfonyl , N- Ethyl-N- (3 , 3-dimethylbutyl) -aminosulfonyl, N- Ethyl-N- (1-ethylbutyl) -aminosulfonyl, N-Ethyl-N- (2-ethyl- butyl) -aminosulfonyl, N-Ethyl-N- (1, 1, 2-trimethyl - propyl) -aminosulfonyl, N-Ethyl-N- (1,2, 2-trimethyl - propyl) -aminosulfonyl , N-Ethyl-N- ( 1-ethyl-l-methyl - propyl) -aminosulfonyl, N-Ethyl-N- (l-ethyl-2-methylpropyl) -aminosulfonyl, N-Propyl-N-pentylaminosulfonyl, N-Butyl-N-pentylaminosulfonyl, N,N-Dipentylaminosulfonyl,(1, 1-dimethylbutyl) aminosulfonyl, N-methyl-N- (1, 2-dimethylbutyl) aminosulfonyl, N-methyl-N- (1, 3-dimethylbutyl) aminosulfonyl, N-methyl-N- (2, 2-dimethylbutyl) aminosulfonyl, N-methyl-N- (2, 3-dimethylbutyl) aminosulfonyl, N-methyl-N- (3, 3-dimethylbutyl) aminosulfonyl, N-methyl-N- (1 -ethyl-butyl) -aminosulfonyl, N-methyl-N- (2-ethylbutyl) -aminosulfonyl, N-methyl-N- (1, 1, 2-trimethylpropyl) -aminosulfonyl. N-methyl-N- (1,2,2-trimethylpropyl) aminosulfonyl, N-methyl-N- (1-ethyl-l-methylpropyl) aminosulfonyl, N-methyl-N- (l-ethyl-2-methylpropyl ) -aminosulfonyl, N-ethyl-N-pentylaminosulfonyl, N-ethyl-N- (1-methylbutyl) -aminosulfonyl, N-ethyl-N- (2-methylbutyl) -aminosulfonyl, N-ethyl-N- (3-methyl - butyl) -aminosulfonyl, N-ethyl-N- (2,2-dimethylpropyl) -aminosulfonyl, N-ethyl-N- (1-ethylpropyl) -aminosulfonyl, N-ethyl-N-hexylaminosulfonyl, N-ethyl-N- (1, 1-dimethylpropyl) aminosulfonyl, N-ethyl-N- (1, 2-dimethylpropyl) aminosulfonyl, N-ethyl-N- (1-methylpentyl) aminosulfonyl, N-ethyl-N- (2nd -methyl-pentyl) -aminosulfonyl, N-ethyl-N- (3-methylpentyl) -aminosulfonyl, N-ethyl-N- (4-methylpentyl) -aminosulfonyl, N-ethyl-N- (1, 1-dimethylbutyl ) -aminosulfonyl, N-ethyl-N- (1,2-dimethylbutyl) -aminosulfonyl, N-ethyl-N- (1,3-dimethylbutyl) -aminosulfonyl, N-ethyl-N- (2,2-dimethylbutyl) - aminosulfonyl, N-ethyl-N- (2,3-dimethylb tyl) aminosulfonyl, N-ethyl-N- (3, 3-dime thylbutyl) -aminosulfonyl, N-ethyl-N- (1-ethylbutyl) -aminosulfonyl, N-ethyl-N- (2-ethyl-butyl) -aminosulfonyl, N-ethyl-N- (1, 1, 2-trimethyl - propyl) aminosulfonyl, N-ethyl-N- (1,2,2-trimethyl-propyl) -aminosulfonyl, N-ethyl-N- (1-ethyl-l-methyl-propyl) -aminosulfonyl, N-ethyl-N - (l-ethyl-2-methylpropyl) aminosulfonyl, N-propyl-N-pentylaminosulfonyl, N-butyl-N-pentylaminosulfonyl, N, N-dipentylaminosulfonyl,
N-Propyl-N-hexylaminosulfonyl , N-Butyl-N-hexylaminosulfonyl , N-Pentyl-N-hexylaminosulfonyl oder N,N-Dihexylaminosulfonyl;N-propyl-N-hexylaminosulfonyl, N-butyl-N-hexylaminosulfonyl, N-pentyl-N-hexylaminosulfonyl or N, N-dihexylaminosulfonyl;
Di- (Cι-C4~alkyl) amino, sowie die Dialkylaminoreste von Di- (Cι-C4-alkyl) amino-Cι-C4-alkoxycarbonyl und N- (Di-Cι-C4- alkylamino) -imino-Ci-Cg-alkyl, z.B. 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,Di- (-C 4 ~ alkyl) amino, and the dialkylamino residues of di- (-C 4 -C alkyl) amino -C -C 4 -alkoxycarbonyl and N- (Di-Cι-C 4 - alkylamino) -imino- Ci-Cg-alkyl, 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-ethy- lamino, N-Ethyl-N- (1-methylpropyl) amino, N-Ethyl-N- (2-methyl - propyl) 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-methyl - ethyl) amino, N- (1-Methylethyl) -N- (1-methylpropyl) amino,N-methyl-N- (1-methylethyl) amino, N-butyl-N-methylamino, N-methyl-N- (1-methylpropyl) amino, N-methyl-N- (2-methylpropyl) amino, N - (1, 1-Dimethylethyl) -N-methylamino, N-ethyl-N-propylamino, N-ethyl-N- (1-methylethyl) amino, N-butyl-N-ethylamino, 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-methyl-ethyl) amino, N- (1-methylethyl) -N- (1-methylpropyl) amino,
N- (1-Methylethyl) -N- (2-methylpropyl) amino, N- (1, 1-Dimethylethyl) -N- (1-methylethyl) amino, N-Butyl-N- (1-methylpropyl) - amino, N-Butyl-N- (2-methylpropyl) amino, N-Butyl-N- (1 , 1-dime- thylethyl) amino, N- (1-Methylpropyl) -N- (2-methylpropyl) -amino, N- (1, 1-Dimethylethyl) -N- (1-methylpropyl) -amino oder N- (1, 1-Dimethylethyl) -N- (2-methylpropyl) amino;N- (1-methylethyl) -N- (2-methylpropyl) amino, N- (1, 1-dimethylethyl) -N- (1-methylethyl) amino, N-butyl-N- (1-methylpropyl) - amino, N-butyl-N- (2-methylpropyl) amino, N-butyl-N- (1, 1-dimethylethyl) amino, N- (1-methylpropyl) -N- (2-methylpropyl) amino, N- (1, 1-dimethylethyl) -N- (1-methylpropyl) amino or N- (1, 1-dimethylethyl) -N- (2-methylpropyl) amino;
Di- (Ci-Cg-alkyl) amino, sowie die Dialkylaminoreste von Di- (Ci-Cg- alkyl) amino- imino-Ci-Cg- alkyl : Di- (C1-C4-alkyl) amino wie voranstehend genannt, sowie N,N-Dipentylamino, N,N-Di- hexylamino, N-Methyl-N-pentylamino, N-Ethyl -N-pentylamino, N-Methyl-N-hexylamino oder N-Ethyl -N-hexylamino.Di- (Ci-Cg-alkyl) amino, as well as the dialkylamino residues of di- (Ci-Cg-alkyl) amino-imino-Ci-Cg-alkyl: di- (C 1 -C 4 -alkyl) amino as mentioned above, and N, N-dipentylamino, N, N-di-hexylamino, N-methyl-N-pentylamino, N-ethyl -N-pentylamino, N-methyl-N-hexylamino or N-ethyl -N-hexylamino.
Cι-C4-Alkylcarbonyl: z.B. Methylcarbonyl, Ethylcarbonyl, Propylcarbonyl, 1-Methylethylcarbonyl, Butylcarbonyl, 1-Methylpropylcarbonyl, 2-Methylpropylcarbonyl oder 1 , 1-Dimethylethylcarbonyl ;C 1 -C 4 -alkylcarbonyl: for example methylcarbonyl, ethylcarbonyl, propylcarbonyl, 1-methylethylcarbonyl, butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl or 1, 1-dimethylethylcarbonyl;
Ci-Cg-Alkylcarbonyl, sowie die Alkylcarbonylreste vonCi-Cg-alkylcarbonyl, and the alkylcarbonyl radicals of
Ci -Cg -Alkylcarbonylamino, Cι-Cg-Alkylcarbonyl-Cι-Cg-alkyl :Ci -Cg -alkylcarbonylamino, -C-Cg-alkylcarbonyl-Cι-Cg-alkyl:
Cι-C4-Alkylcarbonyl, wie voranstehend genannt, sowie z.B. Pentylcarbonyl, 1-Methylbutylcarbonyl, 2-Methylbutylcarbonyl, 3-Methylbutylcarbonyl, 2, 2-Dimethylpropylcarbonyl, 1-Ethyl- propylcarbonyl, Hexylcarbonyl, 1, 1-Dimethylpropylcarbonyl, 1, 2-Dimethylpropylcarbonyl, 1-Methylpentylcarbonyl, 2-Methyl- pentylcarbonyl, 3-Methylpe tylcarbonyl, 4-Methylpentyl - carbonyl, 1, 1-Dimethylbutylcarbonyl, 1, 2-Dimethylbutyl - carbonyl, 1, 3-Dimethylbutylcarbonyl, 2 , 2 , -Dimethylbutyl - carbonyl, 2 , 3-Dimethylbutylcarbonyl, 3 , 3-Dimethylbutyl - carbonyl, 1-Ethylbutylcarbonyl, 2-Ethylbutylcarbonyl, 1,1, 2-Trimethylpropylcarbonyl , 1,2, 2-Trimethylpropylcarbonyl , 1-Ethyl-l-methylpropylcarbonyl oder l-Ethyl-2-methylpropyl- carbonyl ;C 1 -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 -Dimethylpropylcarbonyl, 1-methylpentylcarbonyl, 2-methylpentylcarbonyl, 3-methylpentylcarbonyl, 4-methylpentylcarbonyl, 1, 1-dimethylbutylcarbonyl, 1, 2-dimethylbutylcarbonyl, 1, 3-dimethylbutylcarbonyl, 2, 2, -dimethylbutyl - carbonyl, 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;
Cι-C2o-Alkylcarbonyl : Ci-Cg-Alkylcarbonyl, wie voranstehend genannt, sowie Heptylcarbonyl, Octylcarbonyl, Pentadecylcar- bonyl oder Heptadecylcarbonyl;C 1 -C 2 -alkylcarbonyl: C 1 -C 6 -alkylcarbonyl, as mentioned above, and heptylcarbonyl, octylcarbonyl, pentadecylcarbonyl or heptadecylcarbonyl;
Ci-Cg-Halogenalkylcarbonyl : einen Ci-Cg-Alkylcarbonylrest, wie vorstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder Iod substituiert ist, also z.B. Chloracetyl, Dichloracetyl, Trichloracetyl, Fluoracetyl,Ci-Cg-haloalkylcarbonyl: a Ci-Cg-alkylcarbonyl radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, e.g. Chloroacetyl, dichloroacetyl, trichloroacetyl, fluoroacetyl,
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-difluorethylcarbonyl, 2, 2-Dichlor-2-fluorethylcarbonyl, 2 , 2 , 2-Trichlorethyl - carbonyl, Pentafluorethylcarbonyl, 2-Fluorpropylcarbonyl, 3-Fluorpropylcarbonyl, 2 , 2-Difluorpropylcarbonyl, 2,3-Di- fluorpropylcarbonyl, 2-Chlorpropylcarbonyl, 3-Chlorpropylcar- bonyl, 2 , 3-Dichlorpropylcarbonyl, 2-Brompropylcarbonyl, 3-Brompropylcarbonyl, 3,3, 3-Trifluorpropylcarbonyl, 3 , 3 , 3-Trichlorpropylcarbonyl, 2 , 2 , 3 , 3 , 3-Pentafluorpropylcarbonyl, Heptafluorpropylcarbonyl, 1- (Fluormethyl) -2-fluorethylcarbonyl, 1- (Chlormethyl) -2-chlorethylcarbonyl, 1- (Brommethyl) -2-bromethylcarbonyl, 4-Fluorbutylcarbonyl, 4-Chlor- butylcarbonyl, 4-Brombutylcarbonyl , Nonafluorbutylcarbonyl , 5-Fluorpentylcarbonyl, 5 -Chlorpentylcarbonyl , 5 -Brompentyl - carbonyl, Perfluorpentylcarbonyl, 6-Fluorhexylcarbonyl, 6-Chlorhexylcarbonyl, 6 -Bromhexylcarbonyl oder Perfluorhexyl - carbonyl ;Difluoroacetyl, trifluoroacetyl, chlorofluoroacetyl, dichlorofluoracetyl, chlorodifluoroacetyl, 2-fluoroethylcarbonyl, 2-chloroethylcarbonyl, 2-bromoethylcarbonyl, 2-iodoethylcarbonyl, 2, 2-difluoroethylcarbonyl, 2,2, 2-trifluoroethylcarbonyl, 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-di-fluoropropylcarbonyl, 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- (fluoromethyl) -2-fluoroethylcarbonyl, 1- (chloromethyl) -2-chloroethylcarbonyl, 1- (bromomethyl) -2- bromethylcarbonyl, 4-fluorobutylcarbonyl, 4-chlorobutylcarbonyl, 4-bromobutylcarbonyl, nonafluorobutylcarbonyl, 5-fluoropentylcarbonyl, 5-chloropentylcarbonyl, 5-bromopentyl-carbonyl, perfluoropentylcarbonyl, 6-fluorohexylcarbonyl, 6-chlorohexylcarbonyl, 6-bromofluorocarbonyl, 6-bromofluoromethyl,
- Cι-C4-Alkoxycarbonyl, sowie die Alkoxycarbonylteile von Di- (Cι-C4-alkyl) amino-Cι-C4-alkoxycarbonyl, z.B. Methoxy- carbonyl, Ethoxycarbonyl, Propoxycarbonyl , 1-Methylethoxy- carbonyl, Butoxycarbonyl, 1-Methylpropoxycarbonyl, 2-Methyl - propoxycarbonyl oder 1, 1-Dirnethylethoxycarbonyl;- C 1 -C 4 alkoxycarbonyl, and the alkoxycarbonyl parts of di- (C 4 -C 4 alkyl) amino-C 4 -C 4 alkoxycarbonyl, for example methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, 1-methylethoxycarbonyl, butoxycarbonyl, 1- Methylpropoxycarbonyl, 2-methylpropoxycarbonyl or 1, 1-dimethylethyloxycarbonyl;
(Ci-Cg-Alkoxy) carbonyl: (Cι-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,(Ci-Cg-alkoxy) carbonyl: (-C-C 4 alkoxy) carbonyl, as mentioned above, and for example pentoxycarbonyl, 1-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 2, 2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl , Hexoxycarbonyl, 1, 1-dimethylpropoxycarbonyl, 1, 2-dimethylpropoxycarbonyl,
1-Methylpentoxycarbonyl, 2-Methylpentoxycarbonyl, 3-Methyl- pentoxycarbonyl , 4-Methylpentoxycarbonyl, 1, 1-Dimethylbutoxy- carbonyl , 1,2-Dirnethylbutoxycarbony1 , 1,3-Dirnethylbutoxycar- bonyl, 2 , 2-Dimethylbutoxycarbonyl, 2 , 3-Dimethylbutoxycarbo- nyl, 3 , 3-Dimethylbutoxycarbonyl, 1-Ethylbutoxycarbonyl, 2-Ethylbutoxycarbonyl, 1, 1, 2-Trimethylpropoxycarbonyl, 1,2, 2-Trimethylpropoxycarbonyl , 1-Ethyl-l-methyl-propoxy- carbonyl oder 1-Ethyl-2-methyl-propoxycarbonyl;1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1, 1-dimethylbutoxycarbonyl, 1,2-dirnethylbutoxycarbony1, 1,3-dirnethylbutoxycarbonyl, 2, 2-dimethylbutoxycarbonyl, 2, 3- Dimethylbutoxycarbonyl, 3, 3-dimethylbutoxycarbonyl, 1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl, 1, 1, 2-trimethylpropoxycarbonyl, 1,2, 2-trimethylpropoxycarbonyl, 1-ethyl-l-methyl-propoxycarbonyl or 1-ethyl- 2-methyl-propoxycarbonyl;
- Ci-Cg-Halogenalkoxycarbonyl : einen Cι-C4-Alkoxycarbonylrest, wie voranstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder Iod substituiert ist, also z.B. Fluormethoxycarbonyl, Difluormethoxycarbonyl, Trifluor- methoxycarbonyl , Chlordifluormethoxycarbonyl, Bromdifluor- methoxycarbonyl , 2-Fluorethoxycarbonyl, 2-Chlorethoxycar- bonyl, 2-Bromethoxycarbonyl, 2-Iodethoxycarbonyl, 2,2-Di- fluorethoxycarbonyl, 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-Dich- lorpropoxycarbonyl, 3 , 3 , 3-Trifluorpropoxycarbonyl, 3,3,3-Tri- chlorpropoxycarbonyl, 2,2,3,3, 3-Pentafluorpropoxycarbonyl, Heptafluorpropoxycarbonyl, 1- (Fluormethyl) -2-fluorethoxycar- bonyl , 1- (Chlormethyl) -2-chlorethoxycarbonyl, 1- (Brommethyl) - 2-bromethoxycarbonyl, 4-Fluorbutoxycarbonyl, 4-Chlorbutoxy- carbonyl, 4-Brombutoxycarbonyl, 4-Iodbutoxycarbonyl, 5 -Fluor- pentoxycarbonyl , 5 -Chlorpentoxycarbonyl , 5 -Brompentoxycarbo- nyl, 6 -Fluorhexoxycarbonyl, 6 -Chlorhexoxycarbonyl oder 6 -Bromhexoxycarbonyl ;- Ci-Cg-haloalkoxycarbonyl: a -CC 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, bromodifluoro- methoxycarbonyl, 2-fluoroethoxycarbonyl, 2-chloroethoxycarbonyl, 2-bromoethoxycarbonyl, 2-iodoethoxycarbonyl, 2,2-di-fluoroethoxycarbonyl, 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-trichloropropoxycarbonyl, 2,2,3,3, 3-pentafluoropropoxycarbonyl, heptafluoropropoxycarbonyl, 1- (Fluoromethyl) -2-fluoroethoxycarbonyl, 1- (chloromethyl) -2-chloroethoxycarbonyl, 1- (bromomethyl) - 2-bromethoxycarbonyl, 4-fluorobutoxycarbonyl, 4-chlorobutoxycarbonyl, 4-bromobutoxycarbonyl, 4-iodobutoxycarbonyl, 5 - Fluoropentoxycarbonyl, 5-chloropentoxycarbonyl, 5 -bromopentoxycarbonyl, 6 -fluorhexoxycarbonyl, 6 -chlorohexoxycarbonyl or 6 -bromhexoxycarbonyl;
(Cι-C4-Alkyl) carbonyloxy: Acetyloxy, Ethylcarbonyloxy, Propyl- carbonyloxy, 1-Methylethylcarbonyloxy, Butylcarbonyloxy, 1-Methylpropylcarbonyloxy, 2-Methylpropylcarbonyloxy oder 1, 1-Dimethylethylcarbonyloxy;(-C-C 4 alkyl) carbonyloxy: acetyloxy, ethylcarbonyloxy, propylcarbonyloxy, 1-methylethylcarbonyloxy, butylcarbonyloxy, 1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy or 1, 1-dimethylethylcarbonyloxy;
(Cι-C4-Alkylamino) carbonyl: z.B. Methylaminocarbonyl, Ethyl - aminocarbonyl, Propylaminocarbonyl, 1-Methylethylaminocarbo- nyl, Butylaminocarbonyl, 1-Methylpropylaminocarbonyl, 2-Methylpropylaminocarbonyl oder 1, 1-Dimethylethylamino- carbonyl ;(-C-C 4 alkylamino) carbonyl: for example methylaminocarbonyl, ethyl - aminocarbonyl, propylaminocarbonyl, 1-methylethylaminocarbonyl, butylaminocarbonyl, 1-methylpropylaminocarbonyl, 2-methylpropylaminocarbonyl or 1, 1-dimethylethylaminocarbonyl;
(Ci-Cg-Alkylamino) carbonyl : (Cι-C4-Alkylamino) carbonyl, wie vorstehend genannt, sowie z.B. Pentylaminocarbonyl, 1-Methyl- butylaminocarbonyl, 2-Methylbutylaminocarbonyl, 3-Methyl- butylaminocarbonyl, 2, 2-Dimethylpropylaminocarbonyl, 1-Ethyl- propylaminocarbonyl, Hexylaminocarbonyl, 1, 1-Dirnethylpropyl - aminocarbonyl, 1, 2-Dimethylpropylaminocarbonyl, 1-Methylpen- tylaminocarbonyl, 2-Methylpentylaminocarbonyl, 3-Methyl- pentylaminocarbonyl, 4-Methylpentylaminocarbonyl, 1,1-Di- methylbutylaminocarbonyl , 1 , 2-Dimethylbutylaminocarbonyl , 1, 3-Dimethylbutylaminocarbonyl, 2, 2-Dirnethylb tylamino- carbonyl, 2 , 3-Dimethylbutylaminocarbonyl, 3 , 3-Dimethylbutyl - aminocarbonyl, 1-Ethylbutylaminocarbonyl, 2-Ethylbutylamino- carbonyl, 1, 1, 2-Trimethylpropylaminocarbonyl, 1,2,2-Tri- methylpropylaminocarbonyl , 1-Ethyl-l-methylpropylamino- carbonyl oder l-Ethyl-2-methylpropylaminocarbonyl;(Ci-Cg-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-dirnethylpropyl - aminocarbonyl, 1, 2-dimethylpropylaminocarbonyl, 1-methylpentylaminocarbonyl, 2-methylpentylaminocarbonyl, 3-methylpentylaminocarbonyl, 4-methylpentylaminocarbonyl, 1,1-diyl , 2-Dimethylbutylaminocarbonyl, 1, 3-Dimethylbutylaminocarbonyl, 2, 2-Dirnethylb tylaminocarbonyl, 2, 3-Dimethylbutylaminocarbonyl, 3, 3-Dimethylbutyl - aminocarbonyl, 1-Ethylbutylaminocarbonyl, 2-Ethylbutylamino-carbonyl Trimethylpropylaminocarbonyl, 1,2,2-trimethylpropylaminocarbonyl, 1-ethyl-l-methylpropylaminocarbonyl or l-ethyl-2-methylpropylaminocarbonyl;
Di- (Cι-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, -Di- (1-methylpropyl) -aminocarbonyl, N, N-Di- (2-methyl - propyl) -aminocarbonyl , N, N-Di- (1 , 1-dimethylethyl) -aminocarbo- nyl, N-Ethyl-N-methylaminocarbonyl, N-Methyl-N-propylamino- carbonyl, 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-methylpropyl) -aminocarbonyl, N-Ethyl-N- (1, 1-dimethylethyl) -aminocarbonyl, N-(1-Methyl- ethyl) -N-propylaminocarbonyl , N-B tyl-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- (1-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) -amino- carbonyl, N- (1-Methylpropyl) -N- (2-methylpropyl) -aminocarbonyl , N- (1 , 1-Dimethylethyl) -N- ( 1-me hylpropyl) -amino- carbonyl oder N- (1, 1-Dimethylethyl) -N- (2-methylpropyl) -aminocarbonyl ;Di- (-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, -Di- (1-methylpropyl) -aminocarbonyl, N, N-di- (2-methylpropyl) -aminocarbonyl, N, N-di- (1, 1-dimethylethyl) -aminocarbo- nyl, N-ethyl-N-methylaminocarbonyl, N-methyl-N-propylamino-carbonyl, 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-methylpropyl) aminocarbonyl, N-ethyl-N- (1, 1-dimethylethyl) aminocarbonyl, N- (1-methylethyl) - N-propylaminocarbonyl, NB tyl-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- (1-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-me hylpropyl) amino carbonyl or N- (1, 1-dimethylethyl) -N- (2-methylpropyl) aminocarbonyl;
Di- (Ci-Cg-alkyl) -aminocarbonyl : Di- (Cι-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-dimethylpropyl) -aminocarbonyl, N-Methyl-N- (1-ethyl- propyl) -aminocarbonyl , N-Methyl-N-hexylaminocarbonyl , N-Methyl-N- (1, 1-dimethylpropyl) -aminocarbonyl, N-Methyl-N- (1,2-dimethylpropyl) -aminocarbonyl , N-Methyl-N- (1-methyl - pentyl) -aminocarbonyl, N-Methyl-N- (2-methylpentyl) -amino- carbonyl, N-Methyl-N- (3-methylpentyl) -aminocarbonyl,Di- (Ci-Cg-alkyl) -aminocarbonyl: Di- (-C-C 4 -alkyl) -aminocarbonyl, as mentioned above, as well as, for example, N-methyl-N-pentylaminocarbonyl, N-methyl-N- (1-methylbutyl) -aminocarbonyl, N-methyl-N- (2-methylbutyl) -aminocarbonyl, N-methyl-N- (3-methylbutyl) -aminocarbonyl, N-methyl-N- (2, 2-dimethylpropyl) -aminocarbonyl, N-methyl -N- (1-ethyl-propyl) -aminocarbonyl, N-methyl-N-hexylaminocarbonyl, N-methyl-N- (1, 1-dimethylpropyl) -aminocarbonyl, N-methyl-N- (1,2-dimethylpropyl) aminocarbonyl, N-methyl-N- (1-methylpentyl) aminocarbonyl, N-methyl-N- (2-methylpentyl) aminocarbonyl, N-methyl-N- (3-methylpentyl) aminocarbonyl,
N-Methyl-N- (4-methylpentyl) -aminocarbonyl, N-Methyl-N- (1, 1-dimethylbutyl) -aminocarbonyl, N-Methyl-N- (1, 2-dimethyl- butyl) -aminocarbonyl, N-Methyl-N- (1,3-dimethylbutyl) -amino- carbonyl, 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-trimethylpropyl) -aminocarbonyl, N-Methyl- N- (1-ethyl-l-methylpropyl) -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-dimethylpropyl) -aminocarbonyl, N-Ethyl-N- ( 1-ethylpropyl) -aminocarbonyl , N-Ethyl-N-hexylami - nocarbonyl , N-Ethyl-N- ( 1 , 1-dimethylpropyl) -aminocarbonyl , N-Ethyl-N- (1 , 2-dimethylpropyl) -aminocarbonyl, N-Ethyl-N- (1-methylpentyl) -aminocarbonyl, N-Ethyl-N- (2-methylpentyl) - aminocarbonyl, N-Ethyl-N- (3-methylpentyl) -aminocarbonyl, N-Ethyl-N- (4-methylpentyl) -aminocarbonyl, N-Ethyl-N- (1, 1-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 ;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-trimethylpropyl) aminocarbonyl, N-methyl- N- (1-ethyl-l-methylpropyl) 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-dimethylpropyl) aminocarbonyl, N-ethyl-N- (1-ethylpropyl) aminocarbonyl, N- Ethyl-N-hexylamino-nocarbonyl, N-ethyl-N- (1,1-dimethylpropyl) aminocarbonyl, N-ethyl l-N- (1,2-dimethylpropyl) aminocarbonyl, N-ethyl-N- (1-methylpentyl) aminocarbonyl, N-ethyl-N- (2-methylpentyl) aminocarbonyl, N-ethyl-N- (3-methylpentyl) aminocarbonyl, N-ethyl-N- (4-methylpentyl) aminocarbonyl, N-ethyl-N- (1,1-dimethylbutyl) aminocarbonyl, N-ethyl-N- (1,2-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-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 or N, N-dihexylaminocarbonyl;
Di- (Ci-Cg-alkyl) -aminothiocarbonyl : z.B. N, -Dimethylamino- thiocarbonyl , N,N-Diethylaminothiocarbonyl, N, N-Di- (1-methyl - ethyl) aminothiocarbonyl, N,N-Dipropylaminothiocarbonyl,Di- (Ci-Cg-alkyl) -aminothiocarbonyl: e.g. N, -dimethylamino-thiocarbonyl, N, N-diethylaminothiocarbonyl, N, N-di- (1-methyl-ethyl) aminothiocarbonyl, N, N-dipropylaminothiocarbonyl,
N,N-Dibutylaminothiocarbonyl, N,N-Di- (1-methylpropyl) -aminothiocarbonyl, N,N-Di- (2-methylpropyl) -aminothiocarbonyl, N, N-Di- (1, 1-dimethylethyl) -aminothiocarbonyl , N-Ethyl- N-methylaminothiocarbonyl , N-Methyl-N-propylaminothio- carbonyl, N-Methyl-N- (1-methylethyl) -aminothiocarbonyl, N-Butyl-N-methylaminothiocarbonyl , N-Methyl-N- (1-methyl - propyl) -aminothiocarbonyl, N-Methyl-N- (2-methylpropyl) -aminothiocarbonyl , N- (1 , 1-Dimethylethyl ) -N-methylaminothio- carbonyl, N-Ethyl-N-propylaminothiocarbonyl, N-Ethyl-N- (1-methylethyl) -aminothiocarbonyl, N-Butyl-N-ethylaminothiocarbonyl , N-Ethyl-N- (1-methylpropyl) -aminothiocarbonyl , N-Ethyl-N- (2-methylpropyl) -aminothiocarbonyl, N-Ethyl-N- (1, 1-dimethylethyl) -aminothiocarbonyl, N- (1-Methylethyl) - N-propylaminothiocarbonyl , N-Butyl-N-propylaminothiocarbonyl , N- (1-Methylpropyl) -N-propylaminothiocarbonyl, N-(2-Methyl- propyl) -N-propylaminothiocarbonyl, N- (1, 1-Dimethylethyl) - N-propylaminothiocarbonyl, N-Butyl-N- (1-methylethyl) -aminothiocarbonyl , N- (1-Methylethyl) -N- (1-methylpropyl) -aminothio- carbonyl, N- (1-Methylethyl) -N- (2-methylpropyl) -aminothio- carbonyl, N- (1, 1-Dimethylethyl) -N- (1-methylethyl) -aminothiocarbonyl , N-Butyl-N- (1-methylpropyl) -aminothiocarbonyl , N-Butyl-N- (2-methylpropyl) -aminothiocarbonyl, N-Butyl-N- (1, 1-dimethylethyl) -aminothiocarbonyl, N- (1-Methylpropyl) - N- (2-methylpropyl) -aminothiocarbonyl, N- (1, 1-Dimethyl- ethyl) -N- (1-methylpropyl) -aminothiocarbonyl, N- (1, 1-Dimethylethyl) -N- (2-methylpropyl) -aminothiocarbonyl, N-Methyl-N-pen- tylaminothiocarbonyl , N-Methyl-N- ( 1-methylbutyl) -aminothio - carbonyl, N-Methyl-N- (2-methylbutyl) -aminothiocarbonyl, N-Methyl-N- (3-methylbutyl) -aminothiocarbonyl, N-Methyl-N- (2, 2-dimethylpropyl) -aminothiocarbonyl, N-Methyl-N- (1-ethyl- propyl) -aminothiocarbonyl , N-Methyl-N-hexylaminothiocarbonyl , N-Methyl-N- (1, 1-dimethylpropyl) -aminothiocarbonyl, N-Methyl- N- (1, 2-dimethylpropyl) -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-dimethyl- butyl) -aminothiocarbonyl, N-Methyl-N- (2, 3-dimethylbutyl) - aminothiocarbonyl, N-Methyl-N- (3 , 3-dimethylbutyl) -aminothio- carbonyl, N-Methyl-N- (1-ethylbutyl) -aminothiocarbonyl, N-N, N-dibutylaminothiocarbonyl, N, N-di- (1-methylpropyl) aminothiocarbonyl, N, N-di- (2-methylpropyl) aminothiocarbonyl, N, N-di- (1, 1-dimethylethyl) aminothiocarbonyl, N-ethyl-N-methylaminothiocarbonyl, N-methyl-N-propylaminothiocarbonyl, N-methyl-N- (1-methylethyl) aminothiocarbonyl, N-butyl-N-methylaminothiocarbonyl, N-methyl-N- (1-methyl - propyl) -aminothiocarbonyl, N-methyl-N- (2-methylpropyl) -aminothiocarbonyl, N- (1, 1-dimethylethyl) -N-methylaminothio-carbonyl, N-ethyl-N-propylaminothiocarbonyl, N-ethyl-N- (1-methylethyl) aminothiocarbonyl, N-butyl-N-ethylaminothiocarbonyl, N-ethyl-N- (1-methylpropyl) aminothiocarbonyl, N-ethyl-N- (2-methylpropyl) aminothiocarbonyl, N-ethyl-N- (1, 1-dimethylethyl) aminothiocarbonyl, N- (1-methylethyl) - N-propylaminothiocarbonyl, N-butyl-N-propylaminothiocarbonyl, N- (1-methylpropyl) -N-propylaminothiocarbonyl, N- (2-methylpropyl ) -N-propylaminothiocarbonyl, N- (1, 1-dimethylethyl) - N-propylaminothiocarbonyl, N-butyl-N- (1-methylethyl) aminothiocarbonyl, N- (1-methylethyl) -N- (1-methylpropyl) aminothiocarbonyl, N- (1-methylethyl) -N- (2-methylpropyl) aminothiocarbonyl, N- (1, 1-dimethylethyl) -N- (1-methylethyl) aminothiocarbonyl, N-butyl-N- (1-methylpropyl) aminothiocarbonyl, N-butyl-N- (2-methylpropyl) aminothiocarbonyl, N-butyl- N- (1, 1-dimethylethyl) aminothiocarbonyl, N- (1-methylpropyl) - N- (2-methylpropyl) aminothiocarbonyl, N- (1, 1-dimethylethyl) -N- (1-methylpropyl) - aminothiocarbonyl, N- (1, 1-dimethylethyl) -N- (2-methylpropyl) aminothiocarbonyl, N-methyl-N-pentylaminothiocarbonyl, N-methyl-N- (1-methylbutyl) aminothio - carbonyl, N-methyl-N- (2-methylbutyl) aminothiocarbonyl, N-methyl-N- (3-methylbutyl) aminothiocarbonyl, N-methyl-N- (2, 2-dimethylpropyl) aminothiocarbonyl, N-methyl N- (1-ethylpropyl) aminothiocarbonyl, N-methyl-N-hexylaminothiocarbonyl, N-methyl-N- (1, 1-dimethylpropyl) aminothiocarbonyl, N-methyl- N- (1, 2-dimethylpropyl) - aminothiocarbonyl, N-methyl-N- (1-methylpentyl) aminothiocarbonyl, N-methyl-N- (2-methylpentyl) 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- (3rd , 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) -aminothiocarbonyl, N-Methyl-N- (1-ethyl- 2-methylpropyl) -aminothiocarbonyl, N-Ethyl-N-pentylaminothio- carbonyl , N-Ethyl-N- (1-methylbutyl) -amino hiocarbonyl , 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) -amino- thiocarbonyl, N-Ethyl-N-hexylaminothiocarbonyl, N-Ethyl-N- (1, 1-dimethylpropyl) -aminothiocarbonyl, N-Ethyl-N- (1,2- dimethylpropyl) -aminothiocarbonyl, N-Ethyl-N- (1-methyl - pentyl) -aminothiocarbonyl, N-Ethyl-N- (2-methylpentyl) -aminothiocarbonyl , N-Ethyl-N- (3-methylpentyl) -aminothiocarbonyl , N-Ethyl-N- (4-methylpentyl) -aminothiocarbonyl, N-Ethyl-N- (1, 1-dimethylbutyl) -aminothiocarbonyl, N-Ethyl-N- (1,2- dimethylbutyl) -aminothiocarbonyl, N-Ethyl-N- (1, 3-dimethylbutyl) -aminothiocarbonyl, N-Ethyl-N- (2, 2-dimethylbutyl) - aminothiocarbonyl, N-Ethyl-N- (2, 3-dimethylbutyl) -aminothio- carbonyl, 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-trimethyl - propyl) -aminothiocarbonyl , N-Ethyl-N- (1,2, 2-trimethyl - propyl) -aminothiocarbonyl , N-Ethyl-N- (1-ethyl-l-methyl - propyl) -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; Cι-C4-Alkoxy-Cι-C4-alkyl: durch Cι-C -Alkoxy, wie vorstehend genannt, substituiertes Cι-C4-Alkyl, also z.B. für Methoxy- methyl, Ethoxymethyl, Propoxymethyl, (1-Methylethoxy) methyl, Butoxymethyl, ( 1-Methylpropoxy) methyl , (2-Methylpropoxy) - methyl, (1 , 1-Dimethylethoxy) methyl , 2- (Methoxy) ethyl ,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) aminothiocarbonyl, N-methyl-N- (1-ethyl-2-methylpropyl) aminothiocarbonyl, N-ethyl-N-pentylaminothiocarbonyl, N- Ethyl-N- (1-methylbutyl) amino hiocarbonyl, 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) -amino-thiocarbonyl, N-ethyl-N-hexylaminothiocarbonyl, N-ethyl-N- (1, 1-dimethylpropyl) -aminothiocarbonyl, N -Ethyl-N- (1,2-dimethylpropyl) aminothiocarbonyl, N-ethyl-N- (1-methyl-pentyl) -aminothiocarbonyl, N-ethyl-N- (2-methylpentyl) aminothiocarbonyl, N-ethyl-N - (3-methylpentyl) aminothiocarbonyl, N-ethyl-N- (4-methylpentyl) aminothiocarbonyl, N-ethyl-N- (1, 1-dimethylbutyl) aminothiocarbonyl, N-ethyl-N- (1,2- dimethylbutyl) aminot hiocarbonyl, N-ethyl-N- (1, 3-dimethylbutyl) aminothiocarbonyl, N-ethyl-N- (2, 2-dimethylbutyl) - aminothiocarbonyl, N-ethyl-N- (2, 3-dimethylbutyl) aminothio- carbonyl, 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-trimethyl-propyl) aminothiocarbonyl, N-ethyl-N- (1,2, 2-trimethyl-propyl) aminothiocarbonyl, N-ethyl-N- (1-ethyl-l-methyl - propyl) -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 or N, N-dihexylaminothiocarbonyl; C 1 -C 4 -alkoxy-C 4 -alkyl: C 1 -C 4 -alkoxy, as mentioned above, substituted C 1 -C 4 -alkyl, for example for methoxymethyl, ethoxymethyl, propoxymethyl, (1-methylethoxy) methyl , Butoxymethyl, (1-methylpropoxy) methyl, (2-methylpropoxy) methyl, (1, 1-dimethylethoxy) methyl, 2- (methoxy) ethyl,
2- (Ethoxy) ethyl, 2- (Propoxy) ethyl , 2- (1-Methylethoxy) ethyl, 2- (Butoxy) ethyl, 2- (1-Methylpropoxy) ethyl , 2-(2-Methyl- propoxy) ethyl , 2- (1, 1-Dimethylethoxy) ethyl, 2- (Methoxy) - propyl, 2- (Ethoxy) propyl, 2- (Propoxy) propyl, 2-(l-Methyl- ethoxy) -propyl, 2- (Butoxy) propyl, 2- (1-Methylpropoxy) propyl, 2- (2-Methylpropoxy) propyl, 2- (1, 1-Dimethylethoxy) propyl, 3- (Methoxy) propyl, 3- (Ethoxy) -propyl, 3- (Propoxy) propyl, 3- (1-Methylethoxy) propyl, 3- (Butoxy) propyl, 3-(l-Methyl- propoxy) propyl, 3- (2-Methylpropoxy) propyl, 3- (1, 1-Dimethyl - ethoxy) propyl, 2- (Methoxy) butyl, 2- (Ethoxy) butyl, 2- (Propoxy) butyl, 2- (1-Methylethoxy) butyl, 2- (Butoxy) butyl , 2- (1-Methylpropoxy) butyl, 2- (2-Methylpropoxy) butyl, 2- (1, 1-Dimethylethoxy) butyl, 3- (Methoxy) butyl, 3- (Ethoxy) butyl, 3- (Propoxy) butyl, 3- (1-Methylethoxy) butyl, 3- (Butoxy) -butyl, 3- (1-Methylpropoxy) butyl, 3-(2-Methyl- propoxy) butyl , 3- (1, 1-Dimethylethoxy) butyl, 4- (Methoxy) butyl, 4- (Ethoxy) -butyl, 4- (Propoxy) butyl , 4- (1-Methylethoxy) butyl, 4- (Butoxy) -butyl, 4- (1-Methylpropoxy) butyl, 4-(2-Methyl- propoxy) butyl oder 4- (1, 1-Dimethylethoxy) butyl;2- (ethoxy) ethyl, 2- (propoxy) ethyl, 2- (1-methylethoxy) ethyl, 2- (butoxy) ethyl, 2- (1-methylpropoxy) ethyl, 2- (2-methylprooxy) ethyl, 2- (1, 1-dimethylethoxy) ethyl, 2- (methoxy) propyl, 2- (ethoxy) propyl, 2- (propoxy) propyl, 2- (l-methylethoxy) propyl, 2- (butoxy) propyl, 2- (1-methylpropoxy) propyl, 2- (2-methylpropoxy) propyl, 2- (1, 1-dimethylethoxy) propyl, 3- (methoxy) propyl, 3- (ethoxy) propyl, 3- (propoxy ) propyl, 3- (1-methylethoxy) propyl, 3- (butoxy) propyl, 3- (l-methylpropoxy) propyl, 3- (2-methylpropoxy) propyl, 3- (1, 1-dimethylethoxy) propyl, 2- (methoxy) butyl, 2- (ethoxy) butyl, 2- (propoxy) butyl, 2- (1-methylethoxy) butyl, 2- (butoxy) butyl, 2- (1-methylpropoxy) butyl, 2- (2-methylpropoxy) butyl, 2- (1, 1-dimethylethoxy) butyl, 3- (methoxy) butyl, 3- (ethoxy) butyl, 3- (propoxy) butyl, 3- (1-methylethoxy) butyl, 3- (Butoxy) butyl, 3- (1-methylpropoxy) butyl, 3- (2-methylpropoxy) butyl, 3- (1, 1-dimethylethoxy) butyl, 4- (methoxy) butyl, 4- (Ethoxy) butyl, 4- (propoxy) butyl, 4- (1-methylethoxy) butyl, 4- (butoxy) butyl, 4- (1-methylpropoxy) butyl, 4- (2-methylpropoxy) butyl or 4- (1, 1-dimethylethoxy) butyl;
Cι-C4-Alkoxy-Cι-C4-alkoxy, sowie die Alkoxyalkoxyteile von Cι-C4-Alkoxy-Cι-C4-alkoxycarbonyl : durch Cι-C4-Alkoxy, wie vorstehend genannt, substituiertes Cι-C4-Alkoxy, also z.B. für Methoxymethoxy, Ethoxymethoxy, Propoxymethoxy, (1-Methyl- ethoxy) methoxy, Butoxymethoxy, (1-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) propoxy, 2- (1, 1-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;C 1 -C 4 -alkoxy-C 4 -alkoxy, and the alkoxyalkoxy parts of C 1 -C 4 -alkoxy-C 4 -C 4 -alkoxycarbonyl: C 1 -C 4 -alkoxy, as mentioned above, substituted -CC 4 - Alkoxy, e.g. for methoxymethoxy, ethoxymethoxy, propoxymethoxy, (1-methylethoxy) methoxy, butoxymethoxy, (1-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-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-methylpropoxy) propoxy, 2- (1, 1-dimethylethoxy) propoxy, 3- (methoxy) propoxy, 3- (ethoxy) propoxy, 3 - (Propoxy) propoxy, 3- (1-methylethoxy) propoxy, 3- (butoxy) propoxy, 3- (1-methylpropoxy) propoxy, 3- (2-methylpropoxy) propoxy, 3- (1, 1- Dimethylethoxy) propoxy , 2- (methoxy) butoxy, 2- (ethoxy) butoxy, 2- (propoxy) butoxy, 2- (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-methyl- propoxy) 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-methylprooxy) butoxy or 4- (1, 1-dimethylethoxy) butoxy;
C3-Cg-Alkenyl, sowie die Alkenylteile von C3-Cg-Alkenyl- carbonyl, C3-Cg-Alkenyloxy, C -Cg-Alkenyloxycarbonyl, C3-Cg-Alkenylaminocarbonyl, N- (C -Cg-Alkenyl) -N- (Ci-Cg) alkyl - aminocarbonyl, N- (C3-Cg-Alkenyl) -N- (Ci-Cg-alkoxy) aminocarbonyl : 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, 1-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, 1-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 1-Ethyl-2-methyl- prop-2-en-l-yl;C 3 -Cg alkenyl, and the alkenyl parts of C 3 -Cg alkenylcarbonyl, C 3 -Cg alkenyloxy, C -Cg alkenyloxycarbonyl, C 3 -Cg alkenylaminocarbonyl, N- (C -Cg alkenyl) - N- (Ci-Cg) alkyl-aminocarbonyl, N- (C 3 -Cg-alkenyl) -N- (Ci-Cg-alkoxy) aminocarbonyl: e.g. 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-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, 1-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, 1-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 or 1-ethyl-2-methyl-prop- 2-en-l-yl;
C2-Cg-Alkenyl, sowie die Alkenylteile von C2-Cg-Alkenyl- carbonyl, Phenyl-C -Cg-alkenylcarbonyl und Heterocyclyl- C -Cg-alkenylcarbonyl : C3-Cg-Alkenyl, wie voranstehend genannt, sowie Ethenyl;C 2 -Cg alkenyl, and the alkenyl parts of C 2 -Cg alkenylcarbonyl, phenyl-C -Cg alkenylcarbonyl and heterocyclyl-C -Cg alkenylcarbonyl: C 3 -Cg alkenyl, as mentioned above, and ethenyl;
C -Cg-Halogenalkenyl : einen C -Cg-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 -Cg-Alkinyl, sowie die Alkinylteile von C3-Cg-Alkinyl- carbonyl, C3 -Cg-Alkinyloxy, C3-Cg-Alkinyloxycarbony, C3-Cg-Alkinylaminocarbonyl , N- (C3-Cg-Alkinyl) -N- (Ci-Cg- alkyl) -aminocarbonyl, N- (C -Cg-Alkinyl) -N- (Ci-Cg-alkoxy) amino- carbonyl: z.B. Propargyl , But-l-in-3-yl , But-l-in-4-yl ,C -Cg haloalkenyl: a C -Cg 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-dichloroallyl, 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 -Cg alkynyl, and the alkynyl parts of C 3 -Cg alkynylcarbonyl, C 3 -Cg alkynyloxy, C 3 -Cg alkynyloxycarbonyl, C 3 -Cg alkynylaminocarbonyl, N- (C 3 -Cg alkynyl) -N- (Ci-Cg-alkyl) -aminocarbonyl, N- (C-Cg-alkynyl) -N- (Ci-Cg-alkoxy) aminocarbonyl: eg 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-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-But-2-in-1-yl, pent-1-in-3-yl, pent-1-in-4-yl, pent-1-in-5-yl, pent-2-in-1-yl, Pent-2-yn-4-yl, pent-2-yn-5-yl, 3-methyl-but-l-yn-3-yl, 3-methyl-but-l-yn-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;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 or 4-methyl-pent-2-in-5-yl;
C2-Cg-Alkinyl, sowie die Alkinylteile von C -Cg-Alkinyl- carbonyl : C3-Cg-Alkinyl, wie voranstehend genannt, sowie Ethinyl;C 2 -Cg alkynyl, and the alkynyl parts of C -Cg alkynylcarbonyl: C 3 -Cg alkynyl, as mentioned above, and ethynyl;
C3-Cg-Halogenalkinyl : einen C3-Cg-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 -Cg haloalkynyl: a C 3 -Cg 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-1-yl, 4-iodo-but-3-in-1-yl, 5-fluoropent-3-in-1-yl, 5-iodo-pent-4-in-1-yl, 6-fluorine hex-4-in-l-yl or 6-iodo-hex-5-in-l-yl;
C3-Cg-Cycloalkyl, sowie die Cycloalkylteile von C3-Cg-Cyclo- alkylcarbonyl : z.B. Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl;C 3 -Cg cycloalkyl, and the cycloalkyl parts of C 3 -Cg cycloalkylcarbonyl: for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;
Heterocyclyl, sowie Heterocyclylteile von Heterocyclylcarbo- nyl, Heterocyclyl-Ci-Cg-alkyl, Heterocyclyloxycarbonyl, Hete- rocyclyloxythiocarbonyl , Heterocyclylcarbonyl-Ci-Cg-alkyl , N- (Ci-Cg-Alkyl) -N- (heterocyclyl) -aminocarbonyl, Heterocyclyla- minocarbonyl : 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 mit einem Heteroatom:Heterocyclyl, and also heterocyclyl parts of heterocyclylcarbonyl, heterocyclyl-Ci-Cg-alkyl, heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl, heterocyclylcarbonyl-Ci-Cg-alkyl, N- (Ci-Cg-alkylclycylyl) -N- (hetero- minocarbonyl: a saturated, partially saturated or unsaturated 5- or 6-membered, C-bonded, heterocyclic ring which contains one to four identical or different heteroatoms selected from the following group: oxygen, sulfur or nitrogen, so for example 5-membered rings with one heteroatom:
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-dihydro- thien-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, 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 ,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, 3,4-dihydro-2H-pyrrol-2-yl, 3, 4-dihydro-2H-pyrrol-3-yl,
3 , 4-Dihydro-5H-pyrrol-2-yl, 3 , 4-Dihydro-5H-pyrrol-3-yl , 2-Furyl, 3-Furyl, 2-Thienyl, 3-Thienyl, Pyrrol-2-yl oder Pyrrol-3-yl;3, 4-dihydro-5H-pyrrol-2-yl, 3, 4-dihydro-5H-pyrrol-3-yl, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, pyrrol-2-yl or Pyrrol-3-yl;
5-gliedrige Ringe mit 2 Heteroatomen wie: Tetrahydropyra- zol-3-yl, Tetrahydropyrazol-4-yl, Tetrahydroisoxazol-3-yl , Tetrahydroisoxazol-4-yl, Tetrahydroisoxazol-5-yl, 1,2-Oxa- thiolan-3-yl, 1, 2-Oxathiolan-4-yl , 1 , 2-Oxathiolan-5-yl, Te- trahydroisothiazol-3-yl, Tetrahydroisothiazol-4-yl, Tetrahy- droisothiazol-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,5-membered rings with 2 heteroatoms such as: tetrahydropyrazole-3-yl, tetrahydropyrazol-4-yl, tetrahydroisoxazol-3-yl, tetrahydroisoxazol-4-yl, tetrahydroisoxazol-5-yl, 1,2-oxathiolane -yl, 1,2-oxathiolan-4-yl, 1,2-oxathiolan-5-yl, tetrahydroisothiazol-3-yl, tetrahydroisothiazol-4-yl, tetrahydroisothiazol-5-yl, 1,2-dithiolane -3- yl, 1,2-dithiolan-4-yl, tetrahydroimidazol-2-yl, tetrahydroimidazol-4-yl, tetrahydrooxazol-2-yl, tetrahydrooxazol-4-yl, tetrahydrooxazol-5-yl, tetrahydr -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,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,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-Dihydroi - sothiazol-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 oder Thiazol-5-yl;2, 5-dihydro-1H-pyrazol-4-yl, 2, 5-dihydro-1H-pyrazol-5-yl, 4, 5-dihydroisoxazol-3-yl, 4, 5-dihydroisoxazol-4-yl, 4, 5-dihydroisoxazol-5-yl, 2,5-dihydroisoxazol-3-yl, 2,5-dihydroisoxazol-4-yl, 2,5-dihydroisoxazol-5-yl, 2,3-dihydroisoxazol-3- yl, 2, 3-dihydroisoxazol-4-yl, 2, 3-dihydroisoxazol-5-yl, 4,5-dihydroisothiazol-3-yl, 4, 5-dihydroisothiazol-4-yl, 4, 5-dihydroi - sothiazol-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-imi-dazol-4-yl, 4,5-dihydro-lH-imidazole -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-dihydrooxa zol-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, 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 or thiazol-5-yl;
5-gliedrige Ringe mit 3 Heteroatomen wie: 1, 2, 3-Δ2-Oxadiazo- lin-4-yl, 1, 2 , 3-Δ2-Oxadiazolin-5-yl , 1, 2 , 4-Δ4-Oxadiazo- lin-3-yl, 1, 2 , 4-Δ4-Oxadiazolin-5-yl, 1, 2 , 4-Δ2-Oxadiazo- lin-3-yl, 1, 2 , 4-Δ2-Oxadiazolin-5-yl, 1, 2 , 4-Δ3-Oxadiazo- lin-3-yl, 1, 2, 4-Δ3-Oxadiazolin-5-yl, 1, 3 , 4-Δ2-Oxadiazo- lin-2-yl, 1, 3 , 4-Δ2-Oxadiazolin-5-yl , 1, 3 , 4-Δ3-Oxadiazo- lin-2-yl, 1, 3 , 4-Oxadiazolin-2-yl, 1, 2 , 4-Δ -Thiadiazolin-3-yl, 1,2, 4-Δ-Thiadiazolin-5-yl , 1,2, 4-Δ3-Thiadiazolin-3-yl , 1,2, 4-Δ3-Thiadiazolin-5-yl , 1,2, 4-Δ2-Thiadiazolin-3-yl , l,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 , 1,3, 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 , l,2,4-Δ3-Triazolin-3-yl, 1, 2 , 4-Δ3-Triazolin-5-yl, l,2,4-Δ1-Triazolin-2-yl, 1, 2, 4-Triazolin-3-yl, 3H-1,2,4-Di- thiazol-5-yl, 2H-1, 3 , 4-Dithiazol-5- yl, 2H-l,3,4-Oxathiazol-5-yl, 1, 2 , 3-Oxadiazol-4-yl,5-membered rings with 3 heteroatoms such as: 1, 2, 3-Δ 2 -oxadiazo-lin-4-yl, 1, 2, 3-Δ 2 -oxadiazolin-5-yl, 1, 2, 4-Δ 4 - Oxadiazo-lin-3-yl, 1, 2, 4-Δ 4 -oxadiazolin-5-yl, 1, 2, 4-Δ 2 -Oxadiazo-lin-3-yl, 1, 2, 4-Δ 2 -oxadiazolin -5-yl, 1, 2, 4-Δ 3 -Oxadiazo-lin-3-yl, 1, 2, 4-Δ 3 -Oxadiazolin-5-yl, 1, 3, 4-Δ 2 -Oxadiazo- lin- 2-yl, 1, 3, 4-Δ 2 -oxadiazolin-5-yl, 1, 3, 4-Δ 3 -oxadiazolin-2-yl, 1, 3, 4-oxadiazolin-2-yl, 1, 2, 4-Δ-thiadiazolin-3-yl, 1,2, 4-Δ-thiadiazolin-5-yl, 1,2, 4-Δ 3 -thiadiazolin-3-yl, 1,2, 4-Δ 3 - Thiadiazolin-5-yl, 1,2, 4-Δ 2 -thiiaziaz-3-yl, l, 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, 1,3, 2-dioxathiolane -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, l, 2,4-Δ 3 -Triazolin-yl-3, 1, 2, 4-Δ 3 -Triazolin-yl-5, l, 2.4 -Δ 1 -triazolin-2-yl, 1, 2, 4-triazolin-3-yl, 3H-1,2,4-di-thiazol-5-yl, 2H-1, 3, 4-dithiazol-5-yl, 2H-l, 3,4-oxathiazole 5-yl, 1, 2, 3-oxadiazol-4-yl,
1,2, 3-Oxadiazol-5-yl, 1,2, 4-Oxadiazol-3-yl, 1,2, 4,-Oxadiazol-5-yl, 1, 3 , 4-Oxadiazol-2-yl, 1 , 2 , 3-Thiadiazol-4-yl , 1,2 , 3-Thiadiazol-5-yl , 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 oder 1, 2 , 4-Triazol-3-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, 1st , 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 or 1, 2, 4-triazol-3-yl;
5-gliedrige Ringe mit 4 Heteroatomen wie: Tetrazol-5-yl,5-membered rings with 4 heteroatoms such as: tetrazol-5-yl,
6-gliedrige Ringe mit einem Heteroatom wie:6-membered rings with a heteroatom 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 , 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-5 , 6-Dihydropyran-6-yl , 2H-5 , 6-Dihydrothiopyran-2-yl , 2H-5, 6-Dihydrothiopyran-3-yl, 2H-5, 6-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, 1,2, 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, 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 , 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 oder Pyridin-4-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, 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, 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- 5, 6-dihydropyran-6-yl, 2H-5, 6-dihydrothiopyran-2-yl, 2H-5, 6-dihydrothiopyran-3-yl, 2H-5, 6-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, 1,2, 5, 6-tetrahydropyridin-4-yl, 1, 2, 5, 6-tetrahydropyri - din-5-yl, 1, 2, 5, 6-tetrahydropyridin-6-yl, 2, 3, 4, 5-tetrahydropyridin-2-yl, 2, 3, 4, 5-tetrahydropyridin-3-yl, 2, 3, 4, 5-tetrahydropyridin-4-yl, 2,3,4, 5-tetrahydropyridin-5-yl, 2, 3,4, 5-tetrahydropyridin-6-yl, 4H-pyran-2- yl, 4H-pyran-3-yl, 4H-pyran-4-yl, 4H-thiopyran-2-yl, 4H-thiopyran-3-yl, 4H-thiopyran-4-yl, 1, 4-dihydropyridin-2- yl, 1,4-dihydropyridin-3-yl, 1,4-dihydropyridin-4-yl, 2H-pyran-2-yl, 2H-pyran-3-yl, 2H-pyran-4-yl, 2H- Pyran-5-yl, 2H-pyran-6-yl, 2H-thiopyran-2-yl, 2H-thiopyran-3-yl, 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-dihydropyridi n-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 or pyridin-4-yl;
6-gliedrige Ringe mit zwei Heteroatomen wie: 1, 3-Dioxan-2-yl,6-membered rings with two heteroatoms such as: 1, 3-dioxan-2-yl,
1, 3-Dioxan-4-yl, 1,3-Dioxan-1,3-dioxan-4-yl, 1,3-dioxane
5-yl, 1, 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 ,5-yl, 1,4-dioxan-2-yl, 1,3-dithian-2-yl, 1,3-dithian-4-yl, 1,3-dithian-5-yl, 1,4-dithiane 2-yl, 1, 3-oxathian-2-yl,
1, 3-Oxathian-4-yl, 1, 3-Oxathian-5-yl , 1, 3-Oxathian-6-yl, 1, 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-l,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- l,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- 1, 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 , 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,1, 3-oxathian-4-yl, 1, 3-oxathian-5-yl, 1, 3-oxathian-6-yl, 1, 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, tetrahydro-1, 3-oxazin-2-yl, tetrahydro-1, 3-oxazin-4-yl, tetrahydro-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-l, 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-dihydro-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-oxazine-3-yl, 4H-5, 6-dihydro-l, 2- oxazin-4-yl, 4H-5, 6-dihydro-l, 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-thiazin-6-yl, 2H-3, 6-dihydro-l, 2-oxazin-3-yl, 2H-3, 6-dihydro-1, 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-dihydro-l, 2-oxazin-4- yl, 2H-3,4-dihydro-1, 2-oxazin-5-yl, 2H-3,4, 4-dihydro-l, 2-oxazin-6-yl, 2H-3,4, 4-dihydro-l, 2-thiazin-3-yl, 2H-3, 4-dihydro-l, 2-thiazin-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- 1, 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,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-1,3-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-tetrahydropyrazin-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 ,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-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-dihydro-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-1, 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-thiazin-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-1, 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, 4H-1, 3-Oxazin-2-yl, 4H-1, 3-0xazin- 4-yl, 4H-1, 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 ,6H-1, 2-oxazin-3-yl, 6H-1, 2-oxazin-4-yl, 6H-1, 2-oxazin-5-yl, 6H-1, 2-oxazin-6-yl, 6H- 1, 2-thiazin-3-yl, 6H-1, 2-thiazin-4-yl, 6H-1, 2-thiazin-5-yl, 6H-1, 2-thiazin-6-yl, 2H-1, 3-oxazin-2-yl, 2H-1, 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, 4H-1, 3-oxazin- 2-yl, 4H-1, 3-0xazin-4-yl, 4H-1, 3-oxazin-5-yl, 4H-1, 3-oxazin-6-yl, 4H-1, 3-thiazine 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-oxazin-5-yl, 6H-1, 3-oxazin-6-yl, 6H-1, 3-thiazine 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, 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 oder Pyrazin-2-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-1, 4-oxazin-3-yl, 4H-1, 4-thiazin-2-yl, 4H-1, 4-thiazin-3-yl, 1,4-dihydropyridazin-3-yl, 1,4-dihydropyridazin-4-yl, 1,4-dihydropyridazin-5-yl, 1,4-dihydropyridazin-6-yl, 1,4-dihydropyrazine-2-yl, 1,2-dihydropyrazine-2-yl, 1,2-dihydropyrazine-3-yl, 1,2-dihydropyrazine-5-yl, 1,2-dihydropyrazine-6- yl, 1,4-dihydropyrimidin-2-yl, 1,4-dihydropyrimidin-4-yl, 1,4-dihydropyrimidin-5-yl, 1,4-dihydropyrimidin-6-yl, 3,4-dihydro- pyrimidin-2-yl, 3,4-dihydropyrimidin-4-yl, 3,4-dihydropyrimi-din-5-yl or 3,4,4-dihydropyrimidin-6-yl, pyridazin-3-yl, pyridazin-4-yl, Pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl or pyrazin-2-yl;
6-gliedrige Ringe mit 3 Heteroatomen wie: 1, 3 , 5-Triazin-2-yl, l,2,4-Triazin-3-yl, 1, 2, 4-Triazin-5-yl oder 1,2,4-Tri- azin-6-yl;6-membered rings with 3 heteroatoms such as: 1, 3, 5-triazin-2-yl, l, 2,4-triazin-3-yl, 1, 2, 4-triazin-5-yl or 1,2,4 -Triazine-6-yl;
6-gliedrige Ringe mit 4 Heteroatomen wie: l,2,4,5-Tetrazin-3-yl;6-membered rings with 4 heteroatoms such as: l, 2,4,5-tetrazin-3-yl;
wobei ggf. der Schwefel der genannten Heterocyclen zu S=0 oder S(=0)2 oxidiert sein kannwhere 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-Cg-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 -Cg 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: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,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 , 4-Δ -Oxadiazolin-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, 4-Δ3-Triazolin-l-yl, 1,2, 4-Δ1- Triazolin-4-yl, 1, 2 , 3-Triazol-l-yl , 1, 2 , 4-Triazol-l-yl , Tetrazol-1-yl;Tetrahydroisoxazol-2-yl, tetrahydroisothiazol-2-yl, tetrahydroimidazol-1-yl, tetrahydrooxazol-3-yl, tetrahydrothia zol-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, 4-Δ-oxadiazolin-2-yl, 1, 2, 4-Δ 2 -oxadiazolin-4-yl, 1, 2, 4 -Δ 3 -oxadiazolin-2-yl, 1, 3, 4-Δ 2 -oxadiazo-lin-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, l, 2,4-Δ 2 -triazolin-4-yl, 1, 2, 4-Δ 3 -triazolin-l-yl , 1,2,4-Δ 1 - triazolin-4-yl, 1,2,3-triazol-l-yl, 1,2,4-triazol-l-yl, tetrazol-1-yl;
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- oxazin-2-yl, 2H-3 , 4-Dihydro-l, 2-thiazin-2-yl, 2 , 3 , 4 , 5-Tetra- hydropyridazin-2-yl , 1,2,5, 6-Tetrahydropyridazin-l-yl , 1,2,5, 6-Tetrahydropyridazin-2-yl, 1,2,3, 6-Tetrahydropyrida- zin-l-yl, 3 , 4 , 5 , 6-Tetrahydropyrimidin-3-yl, 1, 2 , 3 , 4-Tetrahy- dropyrazin-1-yl, 1, 2, 3 , 4-Tetrahydropyrimidin-l-yl,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-oxazin-2-yl, 2H-3,4, 4-dihydro-l, 2-thiazin-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-tetrahydropyridazin-l-yl, 3, 4, 5, 6-tetrahydropyrimidin-3-yl, 1, 2, 3, 4-tetrahydropyrazin-1-yl, 1, 2, 3, 4-tetrahydropyrimidin-l-yl,
1,2,3, 4-Tetrahydropyrimidin-3-yl, 2 , 3-Dihdro-l, 4-thiazin- 4-yl, 2H-l,2-Oxazin-2-yl, 2H-1, 2-Thiazin-2-yl , 4H-l,4-Oxa- zin-4-yl, 4H-1, 4-Thiazin-4-yl, 1, 4-Dihydropyridazin-l-yl, 1, 4-Dihydropyrazin-l-yl, 1, 2-Dihydropyrazin-l-yl, 1,4-Dihy- dropyrimidin-1-yl oder 3 , 4-Dihydropyrimidin-3-yl, sowie N-gebundene cyclische Imide wie:1,2,3,4-tetrahydropyrimidin-3-yl, 2,3-dihdro-1,4-thiazine-4-yl, 2H-1,2-oxazin-2-yl, 2H-1,2-thiazine 2-yl, 4H-l, 4-oxazine-4-yl, 4H-1,4, thiazin-4-yl, 1,4-dihydropyridazin-l-yl, 1,4-dihydropyrazine-l-yl, 1, 2-dihydropyrazin-l-yl, 1,4-dihydropyrimidin-1-yl or 3, 4-dihydropyrimidin-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-Ci-Cg-alkyl, Phenylcarbonyl-Ci-Cg-alkyl, Phenyl - carbonyl, Phenylalkenylcarbonyl, Phenoxycarbonyl, Phenylamino- carbonyl und N- (Ci-Cg-Alkyl) -N-phenylaminocarbonyl bzw. Heterocyc- lylkomponenten in Heterocyclyl-Ci-Cg-alkyl, Heterocyclylcarbonyl- Ci-Cg-alkyl, Heterocyclylcarbonyl, Heterocyclylalkenylcarbonyl, Heterocyclyloxycarbonyl, Heterocyclylaminocarbonyl und N(Cι-Cg-Alkyl) -N-heterocyclylaminocarbonyl sind, soweit nicht an- ders angegeben, vorzugsweise unsubstituiert oder tragen ein bis drei Halogenatome und/oder eine Nitrogruppe, einen Cyanorest und/ oder einen oder zwei Methyl-, Trifluormethyl-, Methoxy- oder Tri- fluormethoxysubstituenten.All phenyl rings or heterocyclyl residues and all phenyl components in phenyl-Ci-Cg-alkyl, phenylcarbonyl-Ci-Cg-alkyl, phenyl-carbonyl, phenylalkenylcarbonyl, phenoxycarbonyl, phenylamino-carbonyl and N- (Ci-Cg-alkyl) -N -phenylaminocarbonyl or heterocyclyl components in heterocyclyl-Ci-Cg-alkyl, heterocyclylcarbonyl-Ci-Cg-alkyl, heterocyclylcarbonyl, heterocyclylalkenylcarbonyl, heterocyclyloxycarbonyl, heterocyclylaminocarbonyl and N (Cι -Noc-heterocyl) are not otherwise specified, 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 R7 = Ha werden als Verbindungen der Formel la sowie Verbindungen der Formel I mit R7 = Ilb als Ib bezeichnet.The compounds of the formula I according to the invention with R 7 = Ha are referred to as compounds of the formula Ia and compounds of the formula I with R 7 = Ilb as Ib.
In Hinblick auf die Verwendung der erfindungsgemäßen Verbindungen der Formel I als Herbizide haben die Variablen vorzugsweise folgende Bedeutungen, und zwar jeweils für sich allein oder in Kombination:With regard to the use of the compounds of the formula I according to the invention as herbicides, the variables preferably have the following meanings, in each case individually or in combination:
X S(=0)2 oder CRR5;XS (= 0) 2 or CRR 5 ;
R1 Nitro, Halogen, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl ,R 1 nitro, halogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl,
Ci-Cg-Alkoxy, Ci-Cg-Halogenalkoxy, Ci-Cg-Alkylthio, Ci-Cg-Halogenalkylthio, Ci-Cg-Alkylsulfonyl oder Ci-Cg-Halogenalkylsulfonyl;Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, Ci-Cg-alkylthio, Ci-Cg-haloalkylthio, Ci-Cg-alkylsulfonyl or Ci-Cg-haloalkylsulfonyl;
R3 Wasserstoff;R 3 is hydrogen;
R4,R5 Wasserstoff, Halogen, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, Ci-Cg-Alkoxy, Ci-Cg-Halogenalkoxy, Ci-Cg-Alkylthio,R 4 , R 5 are hydrogen, halogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, Ci-Cg-alkylthio,
Ci-Cg-Halogenalkylthio, Ci-Cg-Alkylsulfonyl oder Ci-Cg-Halogenalkylsulfonyl ;Ci-Cg-haloalkylthio, Ci-Cg-alkylsulfonyl or Ci-Cg-haloalkylsulfonyl;
oderor
R4 und R5 bilden gemeinsam eine -0- (CH2)m-0- , -0- (CH2)m-S- ,R 4 and R 5 together form a -0- (CH 2 ) m -0-, -0- (CH 2 ) m -S-,
-S-(CH )m-S- oder -0- (CH2) n-Kette, die durch einen bis drei Reste aus folgender Gruppe substituiert sein kann: Halogen, Cyano, C1-C4 -Alkyl, C1-C4-Halogenalkyl oder C1-C4 -Alkoxycarbonyl;-S- (CH) m -S- or -0- (CH 2 ) n chain, which can be substituted by one to three radicals from the following group: halogen, cyano, C 1 -C 4 alkyl, C 1 - C 4 haloalkyl or C 1 -C 4 alkoxycarbonyl;
oderor
R4 und R5 bilden gemeinsam eine - (CH2)p-Kette, die durch Sauer- stoff oder Schwefel unterbrochen sein kann und/oder durch einen bis vier Reste aus folgender Gruppe substituiert sein kann:R 4 and R 5 together form a - (CH 2 ) p chain, which can be interrupted by oxygen or sulfur and / or can be substituted by one to four radicals from the following group:
Halogen, Cyano, C1-C4 -Alkyl, Ci -C4 -Halogenalkyl oder Ci -C4 -Alkoxycarbonyl ;Halogen, cyano, C 1 -C 4 alkyl, Ci -C 4 haloalkyl or Ci -C 4 alkoxycarbonyl;
oder R4 und R5 bilden gemeinsam eine Methylidengruppe, die durch einen bis zwei Reste aus folgender Gruppe substituiert sein kann:or R 4 and R 5 together form a methylidene group, which can be substituted by one or two radicals from the following group:
Halogen, Cyano, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, Ci-Cg-Alkoxy oder Ci-Cg-Halogenalkoxy;Halogen, cyano, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkoxy or Ci-Cg-haloalkoxy;
1 0;1 0;
m 2 bis 4;m 2 to 4;
n 1 bis 5 ;n 1 to 5;
p 2 bis 5;p 2 to 5;
R7 eine Verbindung Ha oder IlbR 7 is a compound Ha or Ilb
wobei in which
R8 Halogen, OR10, SR10, S02R1:L< OS02R1:L, OPOR11R12, OPSR11R12,R 8 halogen, OR 10 , SR 10 , S0 2 R 1: L <OS0 2 R 1: L , OPOR 11 R 12 , OPSR 11 R 12 ,
NR13R14, ONR1 R14, N-gebundenes Heterocyclyl oder 0- (N- gebundenes Heterocyclyl), wobei der Heterocyclyl-Rest der beiden letztgenannten Substituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann:NR 13 R 14 , ONR 1 R 14 , N-linked heterocyclyl or 0- (N-linked heterocyclyl), where the heterocyclyl radical of the latter two substituents can be partially or completely halogenated and / or can carry one to three of the following radicals :
Nitro, Cyano, Cι-C4-Alkyl, C1-C4 -Halogenalkyl, Cι-C4-Alkoxy oder C1-C4 -Halogenalkoxy;Nitro, cyano, C 4 alkyl, C 1 -C 4 haloalkyl, Cι-C 4 -alkoxy or C 1 -C 4 -haloalkoxy;
R9 Halogen, Cyano, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, Di- (Ci-Cg- alkoxy) -methyl, Di- (Ci-Cg- alkylthio) -methyl,R 9 halogen, cyano, Ci-Cg-alkyl, Ci-Cg-haloalkyl, di- (Ci-Cg-alkoxy) -methyl, di- (Ci-Cg-alkylthio) -methyl,
(Ci-Cg-Alkoxy) (Ci-Cg-alkylthio) -methyl, Hydroxy, Ci-Cg-Alkoxy, Ci-Cg-Halogenalkoxy, Ci-Cg-Alkylthio, Ci-Cg-Halogenalkylthio, Ci-Cg-Alkylsulfonyl, Cι~Cg- Halogenalkylsulfonyl, Ci-Cg-Alkylcarbonyl, Ci-Cg-Halo- genalkylcarbonyl, Ci-Cg-Alkoxycarbonyl oder Ci-Cg-Halo- genalkoxycarbonyl ;(Ci-Cg-alkoxy) (Ci-Cg-alkylthio) methyl, hydroxy, Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, Ci-Cg-alkylthio, Ci-Cg-haloalkylthio, Ci-Cg-alkylsulfonyl, Cι ~ Cg-haloalkylsulfonyl, Ci-Cg-alkylcarbonyl, Ci-Cg-haloalkylcarbonyl, Ci-Cg-alkoxycarbonyl or Ci-Cg-haloalkoxycarbonyl;
oder zwei Reste R9 , die am gleichen Kohlenstoff gebunden sind, bilden gemeinsam eine -0- (CH2) m-0- , -0- (CH )m-S - , -S-(CH2)m-S- oder -0- (CH2) n-Kette, die durch einen bis drei Reste aus folgender Gruppe substituiert sein kann: Halogen, Cyano, Cι-C4-Alkyl, Ci -C4-Halogenalkyl oderor two radicals R 9 , which are bonded to the same carbon, together form a -0- (CH 2 ) m -0-, -0- (CH) m -S -, -S- (CH 2 ) m -S- or -0- (CH 2) n chain which may be substituted from the following group by one to three radicals: halogen, cyano, C 4 alkyl, Ci -C4 haloalkyl or
Ci -C4 -Alkoxycarbonyl ;Ci -C 4 alkoxycarbonyl;
oderor
zwei Reste R9, die am gleichen Kohlenstoff gebunden sind, bilden gemeinsam eine - (CH2) p-Kette, die durch Sauerstoff oder Schwefel unterbrochen sein kann und/oder durch einen bis vier Reste aus folgender Gruppe substituiert sein kann: Halogen, Cyano, Cι-C4-Alkyl, C1-C4 -Halogenalkyl odertwo R 9 radicals which are bonded to the same carbon together form a - (CH 2 ) p chain which can be interrupted by oxygen or sulfur and / or can be substituted by one to four radicals from the following group: halogen, cyano , -C-C4 alkyl, C 1 -C 4 haloalkyl or
Ci -C4 -Alkoxycarbonyl ;Ci -C 4 alkoxycarbonyl;
oderor
zwei Reste R9, die am gleichen Kohlenstoff gebunden sind, bilden gemeinsam mit diesem Kohlenstoff eine Carbonylgruppe aus;two radicals R 9 which are bonded to the same carbon form a carbonyl group together with this carbon;
oderor
zwei Reste R9 , die an verschiedenen Kohlenstoffen gebunden sind, bilden gemeinsam eine - (CH ) n-Kette, die durch einen bis drei Reste aus folgender Gruppe substituiert sein kann: Halogen, Ci-Cg-Alkyl, Ci-Cg -Alkoxy, Hydroxy odertwo R 9 radicals, which are bonded to different carbons, together form a - (CH) n chain, which can be substituted by one to three radicals from the following group: halogen, Ci-Cg-alkyl, Ci-Cg -alkoxy, Hydroxy or
Ci -Cg -Alkoxycarbonyl ;Ci -Cg alkoxycarbonyl;
R10 Ci-Cg-Alkyl, C3-Cg-Alkenyl, C3-Cg-Halogenalkenyl,R 10 Ci-Cg-alkyl, C 3 -Cg-alkenyl, C 3 -Cg-haloalkenyl,
C3-Cg-Alkinyl, Cι-C20-Alkylcarbonyl, C2-Cg-Alkenyl- carbonyl, C -Cg-Cycloalkylcarbonyl, Ci-Cg-Alkoxy- carbonyl, C3-Cg-Alkenyloxycarbonyl , C3-Cg-Alkinyloxy- carbonyl, Ci-Cg-Alkylthiocarbonyl, Ci-Cg-Alkylamino carbonyl, C3-Cg-Alkenylaminocarbonyl, C3-Cg-Alkinylami nocarbonyl, N,N-Di- (Ci-Cg-alkyl) -aminocarbonyl, N- (C3-Cg-Alkenyl) -N- (Ci-Cg-alkyl) -aminocarbonyl , N- (C3-Cg-Alkinyl) -N- (Ci-Cg-alkyl) -aminocarbonyl, N- (Ci-Cg-Alkoxy) -N- (Ci-Cg-alkyl) -aminocarbonyl , N- (C3-Cg-Alkenyl) -N- (Ci-Cg-alkoxy) -aminocarbonyl, N- (C3-Cg-Alkinyl) -N- (Ci-Cg-alkoxy) -aminocarbonyl, Di- (Ci-Cg-alkyl) -aminothiocarbonyl, Ci-Cg-Alkylcarbo- nyl-Ci-Cg-alkyl , Cι-Cg-Alkoxyimino-Cι-Cg-alkyl , N- (Ci-Cg-Alkylamino) -imino-Ci-Cg-alkyl oder N,N-Di- (Ci-Cg-alkylamino) -imino-Ci-Cg-alkyl, wobei die genannten Alkyl-, Cycloalkyl- und Alkoxyreste partiell oder vollständig halogeniert sein können und/oder eine bis drei der folgenden Gruppen tragen können: Cyano, Cι-C4-Alkoxy, Cι-C4-Alkylthio, Cι-C4~Alkyl- carbonyl, Cι-C4-Alkoxycarbonyl, Hydroxycarbonyl , Di- (Cι-C4~alkyl) -aminocarbonyl, Cι-C4~Alkylcarbonyloxy oder C3-Cg-Cycloalkyl;C 3 -Cg-alkynyl, -C-C 20 alkylcarbonyl, C 2 -Cg-alkenylcarbonyl, C -Cg-cycloalkylcarbonyl, Ci-Cg-alkoxycarbonyl, C 3 -Cg-alkenyloxycarbonyl, C 3 -Cg-alkynyloxy - carbonyl, Ci-Cg-alkylthiocarbonyl, Ci-Cg-alkylamino carbonyl, C 3 -Cg-alkenylaminocarbonyl, C 3 -Cg-alkynylaminocarbonyl, N, N-di- (Ci-Cg-alkyl) -aminocarbonyl, N- ( C 3 -Cg-alkenyl) -N- (Ci-Cg-alkyl) -aminocarbonyl, N- (C 3 -Cg-alkynyl) -N- (Ci-Cg-alkyl) -aminocarbonyl, N- (Ci-Cg- Alkoxy) -N- (Ci-Cg-alkyl) -aminocarbonyl, N- (C 3 -Cg-alkenyl) -N- (Ci-Cg-alkoxy) -aminocarbonyl, N- (C 3 -Cg-alkynyl) -N - (Ci-Cg-alkoxy) -aminocarbonyl, di- (Ci-Cg-alkyl) -aminothiocarbonyl, Ci-Cg-alkylcarbonyl-Ci-Cg-alkyl, -C-Cg-alkoxyimino-Cι-Cg-alkyl, N - (Ci-Cg-Alkylamino) -imino-Ci-Cg-alkyl or N, N-Di- (Ci-Cg-alkylamino) -imino-Ci-Cg-alkyl, where the alkyl, cycloalkyl and alkoxy radicals mentioned can be partially or completely halogenated and / or can carry one to three of the following groups: Cyano, -C 4 alkoxy, -C 4 alkylthio, -C 4 ~ alkylcarbonyl, -C 4 alkoxycarbonyl, hydroxycarbonyl, di- (-C 4 ~ alkyl) -aminocarbonyl, -C-C 4 ~ alkylcarbonyloxy or C 3 -Cg cycloalkyl;
Phenyl, Heterocyclyl, Phenyl-Ci-Cg-alkyl , Heterocy- clyl-Ci-Cg-alkyl, Phenylcarbonyl-Ci-Cg-alkyl , Heterocy- clylcarbonyl-Ci-Cg-alkyl, Phenylcarbonyl, Heterocyclylcarbonyl, Phenoxycarbonyl, Phenyloxythiocarbonyl, Hete- rocyclyloxycarbonyl, Heterocyclyloxythiocarbonyl, Phe- nyl-C-Cg-alkenylcarbonyl oder Heterocyclyl-C2-Cg-alke- nylcarbonyl, wobei der Phenyl- und 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, Cι-C4-Alkyl, Cι-C4-Halogenalkyl ,Phenyl, heterocyclyl, phenyl-Ci-Cg-alkyl, heterocyclyl-Ci-Cg-alkyl, phenylcarbonyl-Ci-Cg-alkyl, heterocyclylcarbonyl-Ci-Cg-alkyl, phenylcarbonyl, heterocyclylcarbonyl, phenoxycarbonyl, phenyloxythiocarbonyl, hetero rocyclyloxycarbonyl, heterocyclyloxythiocarbonyl, phenyl-C-Cg-alkenylcarbonyl or heterocyclyl-C 2 -Cg-alkenylcarbonyl, where the phenyl and heterocyclyl radicals of the 14 latter substituents can be partially or completely halogenated and / or one to three may carry the following radicals: nitro, cyano, C 4 -alkyl, C 4 haloalkyl,
Cι-C4-Alkoxy oder Cι~C4-Halogenalkoxy;Cι-C 4 alkoxy or Cι ~ C 4 haloalkoxy;
R11, R12 Ci-Cg-Alkyl, C3-Cg-Alkenyl, C3-C6-Halogenalkenyl, C -Cg-Cycloalkyl, Hydroxy, Ci-Cg-Alkoxy oder Di- (Ci-Cg-Halogenalkyl) amino, wobei die genanntenR 11 , R 12 Ci-Cg-alkyl, C 3 -Cg-alkenyl, C 3 -C 6 -haloalkenyl, C -Cg-cycloalkyl, hydroxy, Ci-Cg-alkoxy or di- (Ci-Cg-haloalkyl) amino , the said
Alkyl-, Cycloalkyl- und Alkoxyreste partiell oder vollständig halogeniert sein können und/oder eine bis drei der folgenden Gruppen tragen können: Cyano, Cι-C4-Alkoxy, Cι-C4-Alkylthio, Cι-C4-Alkyl- carbonyl, Cι-C4-Alkoxycarbonyl, Hydroxycarbonyl,Alkyl, cycloalkyl and alkoxy radicals can be partially or completely halogenated and / or can carry one to three of the following groups: cyano, C 4 -C 4 -alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylcarbonyl, C 1 -C 4 alkoxycarbonyl, hydroxycarbonyl,
Di- (Cι-C4-alkyl) -aminocarbonyl, Cι-C4~Alkylcarbonyloxy oder C3-Cg-Cycloalkyl;Di- (-C 4 alkyl) aminocarbonyl, -C 4 ~ alkylcarbonyloxy or C 3 -Cg cycloalkyl;
Phenyl, Heterocyclyl, Phenyl-Ci-Cg-alkyl, Heterocy- clyl-Ci-Cg-alkyl, Phenoxy, Heterocyclyloxy, wobei derPhenyl, heterocyclyl, phenyl-Ci-Cg-alkyl, heterocyclyl-Ci-Cg-alkyl, phenoxy, heterocyclyloxy, where the
Phenyl- und der Heterocyclyl-Rest der letztgenannten Substituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, Cι-C4-Alkyl, Cι-C4-Halogenalkyl,Phenyl and the heterocyclyl radical of the lastmentioned substituents may be partially or fully halogenated and / or may carry one to three of the following radicals: nitro, cyano, C 4 -alkyl, C 4 haloalkyl,
Cι-C4~Alkoxy oder Cι-C4-Halogenalkoxy;-C-C 4 ~ alkoxy or -C-C 4 haloalkoxy;
R13 Ci-Cg-Alkyl, C3 -C -Alkenyl, C3 -Cg-Halogenalkenyl ,R 13 Ci-Cg-alkyl, C 3 -C -alkenyl, C 3 -Cg-haloalkenyl,
C3 -C -Cycloalkyl, Ci-C -Alkoxy, C3 -Cg-Alkenyloxy oder Di- (Ci-Cg-Alkyl) -amino, wobei die genannten Alkyl-, Cycloalkyl- und Alkoxyreste partiell oder vollständig halogeniert sein können und/oder einen bis drei Reste der folgenden Gruppe tragen können: Cyano, Cι-C4-Alkoxy, C1-C4 -Alkylthio, Cι-C4-Alkyl- carbonyl, Ci -C4 -Alkoxycarbonyl , Hydroxycarbonyl,C 3 -C cycloalkyl, Ci-C-alkoxy, C 3 -Cg-alkenyloxy or di- (Ci-Cg-alkyl) amino, where the alkyl, Cycloalkyl and alkoxy radicals may be partially or fully halogenated and / or may carry one to three radicals of the following group: cyano, C 4 alkoxy, C 1 -C 4 alkylthio, Cι-C 4 alkyl carbonyl, C -C 4 alkoxycarbonyl, hydroxycarbonyl,
Di- (C1-C4- alkyl) -aminocarbonyl, C1-C4 -Alkylcarbonyloxy oder C3 -Cg-Cycloalkyl;Di (C 1 -C 4 alkyl) aminocarbonyl, C 1 -C 4 alkylcarbonyloxy or C 3 -Cg cycloalkyl;
Phenyl, Heterocyclyl, Phenyl -Ci-Cg- alkyl oder Hetero- cyclyl-Ci-Cg- alkyl, wobei der Phenyl- oder Heterocyclyl-Rest der vier letztgenannten Substituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, C1-C4-Alkyl, C1-C4 -Halogenalkyl, C1-C4-Alkoxy oder C1-C4 -Halogenalkoxy;Phenyl, heterocyclyl, phenyl-Ci-Cg-alkyl or heterocyclic-Ci-Cg-alkyl, where the phenyl or heterocyclyl radical of the four last-mentioned substituents can be partially or completely halogenated and / or carry one to three of the following radicals can: nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy;
R14 Ci-Cg-Alkyl oder C3-Cg-Alkenyl;R 14 Ci-Cg-alkyl or C 3 -Cg-alkenyl;
q 0 bis 6q 0 to 6
Besonders bevorzugt sind Verbindungen der Formel I, wobei die Variablen folgende Bedeutungen haben, und zwar für sich allein oder in Kombination:Compounds of the formula I are particularly preferred, the variables having the following meanings, individually or in combination:
X S(=0) oder CR4R5,XS (= 0) or CR 4 R 5 ,
R1 Halogen, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, Ci-Cg-Alkoxy, Ci-Cg-Alkylthio oder Ci-Cg-Alkylsulfonyl; insbesondere Halogen wie Chlor oder Brom, Cι-C5 -Alkyl wie Methyl oder Ethyl oder Ci-Cg-Alkoxy wie Methoxy oder Ethoxy; besonders bevorzugt Chlor, Methyl oder Methoxy;R 1 is halogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkoxy, Ci-Cg-alkylthio or Ci-Cg-alkylsulfonyl; in particular halogen such as chlorine or bromine, -CC 5 alkyl such as methyl or ethyl or Ci-Cg-alkoxy such as methoxy or ethoxy; particularly preferably chlorine, methyl or methoxy;
R3 Wasserstoff;R 3 is hydrogen;
R ,R5 Wasserstoff, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, Ci-Cg-Alkoxy oder Ci-Cg-Halogenalkoxy, insbesondere Wasserstoff, Ci-Cg-Alkyl oder Ci-Cg-Al- koxy; besonders bevorzugt Wasserstoff oder Ci-Cg-Alkyl wieR, R 5 is hydrogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkoxy or Ci-Cg-haloalkoxy, especially hydrogen, Ci-Cg-alkyl or Ci-Cg-alkoxy; particularly preferably hydrogen or Ci-Cg-alkyl such as
Methyl oder Ethyl; oderMethyl or ethyl; or
R4 und R5 bilden gemeinsam eine -0- (CH2)m-0- , -0-(CH2)m-S- oder -S- (CH )m-S-Kette, die durch einen bis drei Reste aus folgender Gruppe substituiert sein kann: C1-C4 -Alkyl oder C1-C4 -Halogenalkyl; oderR 4 and R 5 together form a -0- (CH 2 ) m -0-, -0- (CH 2 ) m -S- or -S- (CH) m -S chain, which consists of one to three radicals can be substituted from the following group: C 1 -C 4 alkyl or C 1 -C 4 haloalkyl; or
R4 und R5 bilden gemeinsam eine - (CH ) p-Kette, die durch einen bis vier Reste aus folgender Gruppe substituiert sein kann:R 4 and R 5 together form a - (CH) p chain, which can be substituted by one to four radicals from the following group:
Halogen, C1-C4 -Alkyl oder C1-C4 -Halogenalkyl; oderHalogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl; or
R4 und R5 bilden gemeinsam eine Methylidengruppe, die durch einen bis zwei Reste aus folgender Gruppe substituiert sein kann:R 4 and R 5 together form a methylidene group, which can be substituted by one or two radicals from the following group:
Halogen, Cyano, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, Ci-Cg-Alkoxy oder Ci-Cg-Halogenalkoxy;Halogen, cyano, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkoxy or Ci-Cg-haloalkoxy;
1 0;1 0;
m 2 bis 4; insbesondere 2 oder 3m 2 to 4; especially 2 or 3
p 2 bis 5;p 2 to 5;
R7 eine Verbindung Ha oder IlbR 7 is a compound Ha or Ilb
wobei in which
R8 Halogen, OR10, SR10, S02R1:L< OS02R11, NR13R14, ONR1R14,R8 halogen, OR 10 , SR 10 , S0 2 R 1: L <OS0 2 R 11 , NR 13 R 14 , ONR 1 R 14 ,
N-gebundenes Heterocyclyl oder 0- (N-gebundenes Heterocyclyl) , wobei der Heterocyclyl-Rest der beiden letzt- genannten Substituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann:N-linked heterocyclyl or 0- (N-linked heterocyclyl), where the heterocyclyl radical of the latter two substituents can be partially or completely halogenated and / or can carry one to three of the following radicals:
Nitro, Cyano, Cι-C4-Alkyl, C1-C4 -Halogenalkyl, C1-C4-AI- koxy oder C1-C4 -Halogenalkoxy;Nitro, cyano, C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 -alkoxy -AI- or C 1 -C 4 -haloalkoxy;
R9 Halogen, Cyano, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl,R 9 halogen, cyano, Ci-Cg-alkyl, Ci-Cg-haloalkyl,
Di- (Ci-Cg-alkoxy) -methyl, Di- (Cχ-Cg-alkylthio) -methyl, (Ci-Cg -Alkoxy) (Ci-Cg-alkylthio) -methyl, Hydroxy, Ci-Cg-Alkoxy, Ci-Cg-Halogenalkoxy, Ci-Cg-Alkylthio oder Ci-Cg-Halogenalkylthio, oderDi- (Ci-Cg-alkoxy) methyl, di- (Cχ-Cg-alkylthio) methyl, (Ci-Cg-alkoxy) (Ci-Cg-alkylthio) methyl, hydroxy, Ci-Cg-alkoxy, Ci -Cg-haloalkoxy, Ci-Cg-alkylthio or Ci-Cg-haloalkylthio, or
zwei Reste R9 , die am gleichen Kohlenstoff gebunden sind, bilden gemeinsam mit diesem Kohlenstoff eine Carbonylgruppe aus ;two radicals R 9 which are bonded to the same carbon form a carbonyl group together with this carbon;
Rio Ci-Cg-Alkyl, C3-Cg-Alkenyl, C3-Cg-Halogenalkenyl,Rio Ci-Cg-alkyl, C 3 -Cg-alkenyl, C 3 -Cg-haloalkenyl,
C3-Cg-Alkinyl, Cι-C20-Alkylcarbonyl , C3-Cg-Cycloalkyl- carbonyl, Ci-Cg-Alkoxycarbonyl, C3-Cg-Alkenyloxy- carbonyl, Ci-Cg-Alkylaminocarbonyl, C3-Cg-Alkenylamino- carbonyl, N,N-Di- (Ci-Cg-alkyl) -aminocarbonyl, N- (C3-Cg-Alkenyl) -N- (Ci-Cg-alkyl) -aminocarbonyl, N- (Ci-Cg-Alkoxy) -N- (Ci-Cg-alkyl) -aminocarbonyl, N- (C3-Cg-Alkenyl) -N- (Ci-Cg-alkoxy) -aminocarbonyl, Di- (Ci-Cg-alkyl) -aminothiocarbonyl oder Ci-Cg-Alkylcar- bonyl-Ci-Cg-alkyl, wobei die genannten Alkyl-, Cycloalkyl- und Alkoxyreste partiell oder vollständig halogeniert sein können und/oder eine bis drei der folgenden Gruppen tragen können: Cyano, Cι-C4-Alkoxy, Cι-C4-Alkylthio, Cι-C4-Alkyl- carbonyl, Cι-C4-Alkoxycarbonyl, Hydroxycarbonyl, Di- (Cι-C4-alkyl) -aminocarbonyl, Cι-C4-Alkylcarbonyloxy oder C3-Cg-Cycloalkyl;C 3 -Cg-alkynyl, -C-C 20 alkylcarbonyl, C 3 -Cg-cycloalkylcarbonyl, Ci-Cg-alkoxycarbonyl, C 3 -Cg-alkenyloxycarbonyl, Ci-Cg-alkylaminocarbonyl, C 3 -Cg-alkenylamino - carbonyl, N, N-di- (Ci-Cg-alkyl) -aminocarbonyl, N- (C 3 -Cg-alkenyl) -N- (Ci-Cg-alkyl) -aminocarbonyl, N- (Ci-Cg-alkoxy ) -N- (Ci-Cg-alkyl) -aminocarbonyl, N- (C 3 -Cg-alkenyl) -N- (Ci-Cg-alkoxy) -aminocarbonyl, di- (Ci-Cg-alkyl) -aminothiocarbonyl or Ci -Cg-alkylcarbonyl-Ci-Cg-alkyl, where the alkyl, cycloalkyl and alkoxy radicals mentioned can be partially or completely halogenated and / or can carry one to three of the following groups: cyano, -CC 4 -alkoxy, Cι-C 4 alkylthio, Cι-C 4 alkyl carbonyl, Cι-C 4 -alkoxycarbonyl, hydroxycarbonyl, di- (Cι-C4 alkyl) aminocarbonyl, Cι-C 4 alkylcarbonyloxy or C 3 -Cg- Cycloalkyl;
Phenyl, Heterocyclyl, Phenyl-Ci-Cg-alkyl, Heterocy- clyl-Ci-Cg-alkyl, Phenylcarbonyl-Ci-Cg-alkyl , Heterocy- clylcarbonyl-Ci-Cg-alkyl, Phenylcarbonyl, Heterocyclylcarbonyl, Phenoxycarbonyl, Phenyloxythiocarbonyl, Hete- rocyclyloxycarbonyl oder Heterocyclyloxythiocarbonyl, wobei der Phenyl- und der Heterocyclyl-Rest der 12 letztgenannten Substituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, Cι-C4-Alkyl, Cι-C4-Halogenalkyl , Cι-C4-Alkoxy oder Cι-C4~Halogenalkoxy;Phenyl, heterocyclyl, phenyl-Ci-Cg-alkyl, heterocyclyl-Ci-Cg-alkyl, phenylcarbonyl-Ci-Cg-alkyl, heterocyclylcarbonyl-Ci-Cg-alkyl, phenylcarbonyl, heterocyclylcarbonyl, phenoxycarbonyl, phenyloxythiocarbonyl, hetero rocyclyloxycarbonyl or heterocyclyloxythiocarbonyl, where the phenyl and heterocyclyl radicals of the last 12 substituents can be partially or completely halogenated and / or can carry one to three of the following radicals: nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 -Halogenalkyl, -CC 4 alkoxy or -CC 4 ~ haloalkoxy;
R11, R12 Ci-Cg-Alkyl, C3-Cg-Alkenyl , C3-Cg-Halogenalkenyl , C3-Cg-Cycloalkyl, Hydroxy, Ci-Cg-Alkoxy oder Di- (Ci-Cg-Halogenalkyl) amino, wobei die genannten Alkyl-, Cycloalkyl- und Alkoxyreste partiell oder vollständig halogeniert sein können und/oder eine bis drei der folgenden Gruppen tragen können: Cyano, Cι-C4-Alkoxy, Cι-C4-Alkylthio, Cι~C4-Alkyl- carbonyl, Cι-C4-Alkoxycarbonyl , Hydroxycarbonyl, Di- (Cι-C4-alkyl) -aminocarbonyl, Cι-C4-Alkylcarbonyloxy oder C3-Cg-Cycloalkyl; Phenyl, Heterocyclyl, Phenyl-Ci-Cg-alkyl , Heterocy- clyl-Ci-Cg-alkyl, Phenoxy, Heterocyclyloxy, wobei der Phenyl- und der Heterocyclyl-Rest der letztgenannten Substituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann:R 11 , R 12 Ci-Cg-alkyl, C 3 -Cg-alkenyl, C 3 -Cg-haloalkenyl, C 3 -Cg-cycloalkyl, hydroxy, Ci-Cg-alkoxy or di- (Ci-Cg-haloalkyl) amino , where the alkyl, cycloalkyl and alkoxy radicals mentioned can be partially or completely halogenated and / or can carry one to three of the following groups: cyano, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 - Alkyl carbonyl, -C 4 alkoxycarbonyl, hydroxycarbonyl, di (-C 4 alkyl) aminocarbonyl, -C 4 alkylcarbonyloxy or C 3 -Cg cycloalkyl; Phenyl, heterocyclyl, phenyl-Ci-Cg-alkyl, heterocyclyl-Ci-Cg-alkyl, phenoxy, heterocyclyloxy, where the phenyl and the heterocyclyl radical of the latter substituents can be partially or completely halogenated and / or one to three of the following leftovers:
Nitro, Cyano, Cι-C4~Alkyl, Cι-C4-Halogenalkyl, Cι-C4~Alkoxy oder C -C4-Halogenalkoxy;Nitro, cyano, C ~ 4 alkyl, Cι-C4-haloalkyl, Cι-C4 ~ alkoxy or C -C 4 -haloalkoxy;
R13 Ci-Cg -Alkyl, C3 -Cg-Alkenyl , C3 -Cg-Halogenalkenyl ,R 13 Ci-Cg alkyl, C 3 -Cg alkenyl, C 3 -Cg haloalkenyl,
C3-Cg -Cycloalkyl, Ci-Cg -Alkoxy, C -Cg-Alkenyloxy oder Di- (Ci-Cg-Alkyl) -amino, wobei die genannten Alkyl-, Cycloalkyl- und Alkoxyreste partiell oder vollständig halogeniert sein können und/oder einen bis drei Reste der folgenden Gruppe tragen können: Cyano, Cι-C -Alkoxy, Cι-C -Alkylthio, Cι-C -Alkyl- carbonyl, C1-C4 -Alkoxycarbonyl, Hydroxycarbonyl, Di- (C1-C4-alkyl) -aminocarbonyl, Cι-C4-Alkylcarbonyloxy oder C3 -Cg-Cycloalkyl;C 3 -Cg -cycloalkyl, Ci-Cg -alkoxy, C -Cg-alkenyloxy or di- (Ci-Cg-alkyl) -amino, where the alkyl, cycloalkyl and alkoxy radicals mentioned can be partially or completely halogenated and / or can carry one to three radicals of the following group: cyano, -C -alkoxy, -C -CC-alkylthio, -C -C-alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl, hydroxycarbonyl, di- (C1-C4-alkyl ) -aminocarbonyl, -C-C 4 alkylcarbonyloxy or C 3 -Cg cycloalkyl;
Phenyl, Heterocyclyl, Phenyl -Ci-Cg-alkyl oder Heterocyclyl -Ci-C -alkyl, wobei der Phenyl- oder Heterocyclyl-Rest der vier letztgenannten Substituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, Cι-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4 -Alkoxy oder C1-C4 -Halogenalkoxy;Phenyl, heterocyclyl, phenyl -Ci-Cg-alkyl or heterocyclyl -Ci-C -alkyl, where the phenyl or heterocyclyl radical of the four last-mentioned substituents can be partially or completely halogenated and / or can carry one to three of the following radicals: nitro, cyano, C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 -haloalkoxy;
R14 Ci-Cg -Alkyl oder C3 -C -Alkenyl;R 14 Ci-Cg alkyl or C 3 -C alkenyl;
q 0 bis 6q 0 to 6
Insbesondere bevorzugt sind Verbindungen der Formel I, wobeiCompounds of formula I are particularly preferred, wherein
R4 Wasserstoff, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, Ci-Cg-Alkoxy oder Ci-Cg-Halogenalkoxy; besonders bevorzugt Wasserstoff, Ci-Cg-Alkyl wie Methyl oder Ethyl oder Ci-Cg-Alkoxy wie Methoxy oder Ethoxy;R 4 is hydrogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkoxy or Ci-Cg-haloalkoxy; particularly preferably hydrogen, Ci-Cg-alkyl such as methyl or ethyl or Ci-Cg-alkoxy such as methoxy or ethoxy;
R5 Wasserstoff oder Ci -Cg-Alkyl; besonders bevorzugt Wasserstoff oder Methyl;R 5 is hydrogen or C 1 -C 6 -alkyl; particularly preferably hydrogen or methyl;
bedeutenmean
oder R4 und R5 bilden gemeinsam eine -0- (CH2) 2-0- , -0- (CH2) 3-0- ,or R 4 and R 5 together form a -0- (CH 2 ) 2 -0-, -0- (CH 2 ) 3 -0-,
-0- (CH2)2-S-, -0- (CH2.3-S-, -S- (CH2)2-S-, -S- (CH2)3-S-, -(CH2)2-- -(CH2.4 oder - (CH ) 5 -Kette, die durch einen bis drei Cι-C4-Alkyl oder C1-C4 -Halogenalkyl -Reste sub- stituiert sein kann;-0- (CH 2 ) 2 -S-, -0- (CH2. 3 -S-, -S- (CH 2 ) 2 -S-, -S- (CH 2 ) 3 -S-, - (CH 2 ) 2 - - (CH 2 .4 or - (CH) 5 chain, which can be substituted by one to three -CC 4 alkyl or C 1 -C 4 haloalkyl radicals;
oderor
R4 und R5 bilden gemeinsam eine Methylidengruppe, die durch einen Rest der folgenden Gruppe substituiert sein kann:R 4 and R 5 together form a methylidene group which can be substituted by a radical from the following group:
Halogen wie Chlor oder Brom, Ci-Cg-Alkyl wie Methyl oder Ethyl, Ci-Cg-Halogenalkyl wie Chlormethyl, Fluor- methyl, Dichlormethyl, Difluormethyl oder Trifluormethyl , Ci-Cg -Alkoxy wie Methoxy oder Ethoxy.Halogen such as chlorine or bromine, Ci-Cg-alkyl such as methyl or ethyl, Ci-Cg-haloalkyl such as chloromethyl, fluoromethyl, dichloromethyl, difluoromethyl or trifluoromethyl, Ci-Cg-alkoxy such as methoxy or ethoxy.
Insbesonderst bevorzugt sind die Verbindungen der Formel I, wobeiThe compounds of the formula I are particularly preferred, where
R4 Wasserstoff, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, Ci-Cg-Alkoxy oder Ci-Cg-Halogenalkoxy; besonders bevorzugt Wasserstoff, Ci-Cg-Alkyl wie Methyl oder Ethyl oder Ci-Cg-Alkoxy wie Methoxy oder Ethoxy;R 4 is hydrogen, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkoxy or Ci-Cg-haloalkoxy; particularly preferably hydrogen, Ci-Cg-alkyl such as methyl or ethyl or Ci-Cg-alkoxy such as methoxy or ethoxy;
R5 Wasserstoff oder Ci-Cg-Alkyl; besonders bevorzugt Wasserstoff oder Methyl;R 5 is hydrogen or Ci-Cg-alkyl; particularly preferably hydrogen or methyl;
bedeuten.mean.
Ebenso insbesondere bevorzugt sind Verbindungen der Formel I, wobeiLikewise particularly preferred are compounds of formula I, wherein
R9 Nitro, Halogen, Cyano, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, Di- (Ci-Cg-alkoxy) -methyl, Di- (Ci-Cg-alkylthio) -methyl, (Ci-Cg -Alkoxy) (Ci-Cg-alkylthio) -methyl, Hydroxy, Ci-Cg-Alkoxy, Ci-Cg-Halogenalkoxy, Ci-Cg-Alkylthio, Ci-Cg-Halogenalkylthio, Ci-Cg -Alkylsulfinyl, Ci-Cg-Halogenalkylsufinyl , Ci-C -Alkylsulfonyl, Ci-Cg-Halogenalkylsulfonyl, Ci-Cg-Alkylcarbonyl, Ci-Cg-Halogenalkylcarbonyl, Ci-Cg -Alkoxycarbonyl oder Ci-Cg-Halogenalkoxycarbonyl ;R 9 nitro, halogen, cyano, Ci-Cg-alkyl, Ci-Cg-haloalkyl, di- (Ci-Cg-alkoxy) -methyl, di- (Ci-Cg-alkylthio) -methyl, (Ci-Cg-alkoxy ) (Ci-Cg-alkylthio) methyl, hydroxy, Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, Ci-Cg-alkylthio, Ci-Cg-haloalkylthio, Ci-Cg-alkylsulfinyl, Ci-Cg-haloalkylsufinyl, Ci -C -alkylsulfonyl, Ci-Cg-haloalkylsulfonyl, Ci-Cg-alkylcarbonyl, Ci-Cg-haloalkylcarbonyl, Ci-Cg -alkoxycarbonyl or Ci-Cg-haloalkoxycarbonyl;
bedeutetmeans
oder zwei Reste R9, die am gleichen Kohlenstoff gebunden sind, bilden gemeinsam eine -0- (CH2)m-0- , -0- (CH2)m- S - , - S - (CH2) m- S - oder -0- (CH2) n-Kette, die durch einen bis drei Reste aus folgender Gruppe substituiert sein kann: Halogen, Cyano, C1-C4 -Alkyl, C1-C4 -Halogenalkyl oderor two R 9 radicals which are bonded to the same carbon together form a -0- (CH 2 ) m -0-, -0- (CH 2 ) m - S -, - S - (CH 2 ) m - S - or -0- (CH 2 ) n chain, which can be substituted by one to three radicals from the following group: halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or
Ci -C4 -Alkoxycarbonyl ;Ci -C 4 alkoxycarbonyl;
oderor
zwei Reste R , die am gleichen Kohlenstoff gebunden sind, bilden eine - (CH2)p-Kette, die durch Sauerstoff oder Schwefel unterbrochen sein kann und/oder durch einen bis vier Reste aus folgender Gruppe substituiert sein kann: Halogen, Cyano, Cι-C4-Alkyl, C1-C4 -Halogenalkyl oder C1-C4 -Alkoxycarbonyl;two radicals R which are bonded to the same carbon form a - (CH 2 ) p chain which can be interrupted by oxygen or sulfur and / or can be substituted by one to four radicals from the following group: halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 alkoxycarbonyl;
oderor
zwei Reste R9 , die am gleichen Kohlenstoff gebunden sind, bilden gemeinsam mit diesem Kohlenstoff eine Carbonylgruppe aus .two radicals R 9 , which are bonded to the same carbon, form a carbonyl group together with this carbon.
Insbesonderst bevorzugt sind Verbindungen der Formel I, wobeiCompounds of the formula I are particularly preferred, where
R9 Nitro, Halogen, Cyano, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl,R 9 nitro, halogen, cyano, Ci-Cg-alkyl, Ci-Cg-haloalkyl,
Di- (Ci-Cg-alkoxy) -methyl, Di- (Ci-Cg-alkylthio) -methyl, (Ci-Cg-Alkoxy) (Ci-Cg-alkylthio) -methyl, Hydroxy, Ci-Cg-Alkoxy, Ci-Cg-Halogenalkoxy, Ci-Cg-Alkylthio, Ci-Cg-Halogenalkylthio, Ci-C -Alkylsulfinyl, Ci-Cg-Halo- genalkylsufinyl, Ci-Cg -Alkylsulfonyl, Ci-Cg-Halogenalkylsulfonyl, Ci-Cg-Alkylcarbonyl, Ci-Cg-Halogenalkylcarbonyl, Ci-Cg -Alkoxycarbonyl oder Ci-Cg-Halogenalk- oxycarbonyl ;Di- (Ci-Cg-alkoxy) -methyl, di- (Ci-Cg-alkylthio) -methyl, (Ci-Cg-alkoxy) (Ci-Cg-alkylthio) -methyl, hydroxy, Ci-Cg-alkoxy, Ci -Cg-haloalkoxy, Ci-Cg-alkylthio, Ci-Cg-haloalkylthio, Ci-C-alkylsulfinyl, Ci-Cg-haloalkylsufinyl, Ci-Cg-alkylsulfonyl, Ci-Cg-haloalkylsulfonyl, Ci-Cg-alkylcarbonyl, Ci -Cg-haloalkylcarbonyl, Ci-Cg -alkoxycarbonyl or Ci-Cg-haloalkoxycarbonyl;
bedeutetmeans
oderor
zwei Reste R9 , die am gleichen Kohlenstoff gebunden sind, bilden gemeinsam mit diesem Kohlenstoff eine Carbonylgruppe aus .two radicals R 9 , which are bonded to the same carbon, form a carbonyl group together with this carbon.
Ebenso insbesondere bevorzugt sind die Verbindungen der Formel I, wobei R8 NR13R14 oder N-gebundenes Heterocyclyl, das partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, Cι-C4-Alkyl, C1-C4 -Halogenalkyl, C1-C4 -Alkoxy oder Ci -C4-Halogenalkoxy;Likewise particularly preferred are the compounds of formula I, wherein R 8 NR 13 R 14 or N-bonded heterocyclyl which may be partially or fully halogenated and / or may carry one to three of the following radicals: nitro, cyano, C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or Ci -C 4 haloalkoxy;
bedeutet.means.
Ebenso besonders bevorzugt sind die Verbindungen der Formel I, wobeiLikewise particularly preferred are the compounds of formula I, wherein
R8 SR10, NR13R14 oder N-gebundenes Heterocyclyl, wobei derR 8 SR 10 , NR 13 R 14 or N-linked heterocyclyl, the
Heterocyclyl-Rest partiell oder vollständig halogeni- siert sein kann und/oder einen bis drei der folgenden Reste tragen kann:Heterocyclyl radical can be partially or completely halogenated and / or can carry one to three of the following radicals:
Nitro, Cyano, Cι-C4-Alkyl, C1-C4 -Halogenalkyl, C1-C4 -Alkoxy oder C1-C4 -Halogenalkoxy;Nitro, cyano, C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 -haloalkoxy;
Insbesonderst bevorzugt sind Verbindungen der Formel I, wobeiCompounds of the formula I are particularly preferred, where
R8 NR13R14 oder Tetrahydropyrrol -1-yl , 2 , 3 -Dihydro-lH-pyr- rol-l-yl, 2,5-Dihydro-lH-pyrrol-l-yl, Pyrrol-1-yl, Te- trahydropyrazol-1-yl, Tetrahydroisoxazol-2 -yl, Tetrahy- drothiazol-2 -yl, Tetrahydroimidazol-1-yl, Tetrahydroo- xazol-3-yl, Tetrahydrothiazol-3 -yl, Pyrazol-1-yl, Imi- dazol-1-yl, 1, 2, 4 -Triazol -1-yl, Tetrazol - 1 -yl , Piperi- din-l-yl, Hexahydropyrimidin-1-yl, Hexahydropyra- zin-l-yl, Tetrahydro-1, 4-oxazin-4 -yl, Tetrahy- dro-1, 2 -oxazin-2 -yl, Succinimid, Maleinimid oder Gluta- rimid, wobei die genannten Heterocyclen partiell oder vollständig halogeniert sein können und/oder einen bis drei der folgenden Reste tragen können: Nitro, Cyano, Cι-C4-Alkyl, wie Methyl oder Ethyl, C1-C4 -Halogenalkyl wie Chlormethyl, Difluormethyl oder Trifluormethyl, C1-C4 -Alkoxy wie Methoxy oder Ethoxy oder C1-C4 -Halogenalkoxy wie Difluormethoxy oder Tri- fluormethoxy;R 8 NR 13 R 14 or tetrahydropyrrole -1-yl, 2,3-dihydro-lH-pyrrole-l-yl, 2,5-dihydro-lH-pyrrole-l-yl, pyrrol-1-yl, Te - trahydropyrazol-1-yl, tetrahydroisoxazol-2 -yl, tetrahydrothiazol-2 -yl, tetrahydroimidazol-1-yl, tetrahydrooxazol-3-yl, tetrahydrothiazol-3 -yl, pyrazol-1-yl, imidazole -1-yl, 1, 2, 4 -triazole -1-yl, tetrazole-1 -yl, piperidine-l-yl, hexahydropyrimidin-1-yl, hexahydropyrazine-l-yl, tetrahydro-1, 4 -oxazin-4 -yl, tetrahydro-1, 2 -oxazin-2 -yl, succinimide, maleimide or glutarimide, where the heterocycles mentioned can be partially or completely halogenated and / or can carry one to three of the following radicals : Nitro, cyano, -CC 4 alkyl, such as methyl or ethyl, C 1 -C 4 haloalkyl such as chloromethyl, difluoromethyl or trifluoromethyl, C 1 -C 4 alkoxy such as methoxy or ethoxy or C 1 -C 4 haloalkoxy such as difluoromethoxy or trifluoromethoxy;
Weiterhin insbesonderst bevorzugt sind die Verbindungen der For- mel la.The compounds of the formula Ia are also particularly preferred.
Ebenso insbesonderst bevorzugt sind die Verbindungen der Formel la, wobei die Variablen folgende Bedeutungen haben und zwar für sich allein oder in Kombination:The compounds of the formula Ia are also particularly preferred, the variables having the following meanings, either individually or in combination:
X S(=0)2 oder CRR5; R1 Halogen oder Ci -Cg-Alkyl; insbesondere Chlor, Brom oder C1-C4 -Alkyl; besonders bevorzugt Chlor oder Methyl;XS (= 0) 2 or CRR 5 ; R 1 is halogen or C 1 -C 6 -alkyl; especially chlorine, bromine or C 1 -C 4 alkyl; particularly preferably chlorine or methyl;
R3 Wasserstoff;R 3 is hydrogen;
R4 Wasserstoff, Ci-Cg -Alkyl oder Ci - Cβ -Alkoxy; insbesondere Ci-Cg-Alkyl oder Ci-Cg-Alkoxy; besonders bevorzugt Methyl oder Methoxy;R 4 is hydrogen, Ci-Cg alkyl or Ci - Cβ alkoxy; in particular Ci-Cg-alkyl or Ci-Cg-alkoxy; particularly preferably methyl or methoxy;
R5 Wasserstoff oder Ci-Cg -Alkyl: insbesondere Wasserstoff oder Methyl;R 5 is hydrogen or Ci-Cg alkyl: in particular hydrogen or methyl;
0;0;
R8 Halogen, OR10, SR10, SO2R11, NR13Rl4 oder N-gebundenesR 8 halogen, OR 10 , SR 10 , SO 2 R 11 , NR 13 R 14 or N-linked
Heterocyclyl, wobei der Heterocyclyl-Rest partiell oder vollständig halogenisiert sein kann und/oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, Cι-C4-Alkyl, C1-C4 -Halogenalkyl,Heterocyclyl, where the heterocyclyl radical may be partially or fully halogenisiert and / or may carry one to three of the following radicals: nitro, cyano, C 4 alkyl, C 1 -C 4 haloalkyl,
C1-C4 -Alkoxy oder C1-C4 -Halogenalkoxy;C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy;
R9 Ci-C -Alkyl, wie Methyl oder Ethyl; insbesondere Methyl;R 9 Ci-C-alkyl, such as methyl or ethyl; especially methyl;
oderor
zwei Reste R9 , die am gleichen Kohlenstoff gebunden sind, bilden gemeinsam mit diesem Kohlenstoff eine Carbonylgruppe aus;two radicals R 9 which are bonded to the same carbon form a carbonyl group together with this carbon;
R10 Ci-Cg -Alkyl, C3-Cg-Alkenyl oder C3 -Cg-Halogenalkenyl , wobei der Alkyl -Rest partiell oder vollständig halogeniert sein kann und/oder eine bis drei der folgenden Gruppen tragen kann:R 10 Ci-Cg alkyl, C 3 -Cg alkenyl or C 3 -Cg haloalkenyl, where the alkyl radical can be partially or completely halogenated and / or can carry one to three of the following groups:
Cι-C4-Alkoxy, Cι-C4-Alkylcarbonyl oder Cι-C4-Alkoxy- carbonyl ;C 1 -C 4 alkoxy, C 1 -C 4 alkylcarbonyl or C 1 -C 4 alkoxy carbonyl;
Phenyl, Heterocyclyl, Phenyl -Ci-Cg- alkyl, Heterocy- clyl-Ci-Cg- alkyl oder Phenylcarbonyl, wobei die fünf letztgenannten Reste partiell oder vollständig halogeniert sein können und/oder einen bis drei der folgenden Reste tragen können:Phenyl, heterocyclyl, phenyl-Ci-Cg-alkyl, heterocyclyl-Ci-Cg-alkyl or phenylcarbonyl, where the five latter radicals can be partially or completely halogenated and / or can carry one to three of the following radicals:
Nitro, C1-C4 -Alkyl, C1-C4 -Halogenalkyl oder C1-C4-Alkoxy; R11 Ci-Cg-Alkyl, C3 -Cg-Alkenyl oder C3 -Cg-Halogenalkenyl , wobei der Alkyl -Rest partiell oder vollständig halogeniert sein kann und/oder eine bis drei der folgenden Gruppen tragen kann: Cι-C4-Alkoxy, C1-C4 -Alkylcarbonyl oder C1-C4 -Alkoxycarbonyl ;Nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 alkoxy; R 11 Ci-Cg-alkyl, C 3 -Cg-alkenyl or C 3 -Cg-haloalkenyl, where the alkyl radical can be partially or completely halogenated and / or can carry one to three of the following groups: -C-C 4 - Alkoxy, C1-C4 alkylcarbonyl or C 1 -C 4 alkoxycarbonyl;
Phenyl, Heterocyclyl, Phenyl -Ci-Cg- alkyl, Heterocy- clyl-Ci-Cg-alkyl oder Phenylcarbonyl, wobei die fünf letztgenannten Reste partiell oder vollständig halogeniert sein können und/oder einen bis drei der folgenden Reste tragen können:Phenyl, heterocyclyl, phenyl-Ci-Cg-alkyl, heterocyclyl-Ci-Cg-alkyl or phenylcarbonyl, where the five latter radicals can be partially or completely halogenated and / or can carry one to three of the following radicals:
Nitro, C1-C4 -Alkyl, C1-C4 -Halogenalkyl oder Ci -C4-Alkoxy; insbesondere Ci-Cg-Alkyl oder Phenyl, das partiell oder vollständig halogenisiert sein kann;Nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or Ci -C 4 alkoxy; in particular Ci-Cg-alkyl or phenyl, which can be partially or fully halogenated;
R13 Ci-Cg-Alkyl, wie Methyl oder Ethyl;R 13 Ci-Cg-alkyl, such as methyl or ethyl;
R14 Ci-Cg -Alkoxy, wie Methoxy oder Ethoxy;R 14 Ci-Cg alkoxy, such as methoxy or ethoxy;
q 0 bis 6;q 0 to 6;
Besonders bevorzugt sind die Verbindungen der Formel la, wobei:The compounds of the formula Ia are particularly preferred, where:
R8 Halogen, OR10, SR10, S02R1X, NR13R14, 4 -Morpholinyl,R 8 halogen, OR 10 , SR 10 , S0 2 R 1X , NR 13 R 14 , 4 -morpholinyl,
2 -Tetrahydroisoxazolyl, 1-Pyrrolidinyl oder2-tetrahydroisoxazolyl, 1-pyrrolidinyl or
1- (1,2,4-Triazolyl) ;1- (1,2,4-triazolyl);
bedeutet.means.
Außerordentlich bevorzugt sind die Verbindungen der Formel Ial und Ibl (≡ I mit X = CR4R5 und 1, q = 0) , insbesondere die Verbindungen Ial.l bis Ial.342 und die Verbindungen Ibl.l bis Ibl.342, wobei die Restedefinitionen R1 bis R9 , 1 und q nicht nur in Kombination miteinander, sondern auch jeweils für sich allein betrachtet für die erfindungsgemäßen Verbindungen eine besondere Bedeutung haben. Tabelle 1:The compounds of the formula Ial and Ibl (≡ I with X = CR 4 R 5 and 1, q = 0) are particularly preferred, in particular the compounds Ial.l to Ial.342 and the compounds Ibl.l to Ibl.342, where the radical definitions R 1 to R 9 , 1 and q are of particular importance not only in combination with one another, but also in isolation for the compounds according to the invention. Table 1:
0 0
Desweiteren sind folgende Cyclohexenondioxothiochromanoyl -Derivate der Formel I außerordentlich bevorzugt:The following cyclohexenone dioxothiochromanoyl derivatives of the formula I are also extremely preferred:
Die Verbindungen der Formel Ia2 und Ib2 , insbesondere die Verbindungen Ia2.1 bis Ia2.342 und die Verbindungen Ib2.1 bis Ib2.342, die sich von den Verbindungen lal.l bis Ial.342 bzw. Ibl.l bis Ibl.342 dadurch unterscheiden, daß (R9)g "5,5-Dimethyl" bedeutet. The compounds of the formula Ia2 and Ib2, in particular the compounds Ia2.1 to Ia2.342 and the compounds Ib2.1 to Ib2.342, which differ from the compounds Ial.l to Ial.342 or Ibl.l to Ibl.342 distinguish in that (R 9 ) g means "5,5-dimethyl".
Ia2 Ib2Ia2 Ib2
Die Verbindungen der Formel Ia3 und Ib3, insbesondere die Verbindungen Ia3.1 bis Ia3.342 und die Verbindungen Ib3.1 bisThe compounds of the formula Ia3 and Ib3, in particular the compounds Ia3.1 to Ia3.342 and the compounds Ib3.1 to
Ib3.342, die sich von den Verbindungen lal.l bis Ial.342 bzw. Ibl.l bis Ibl.342 dadurch unterscheiden, daß R9 g "5 -Methyl" bedeutet.Ib3.342, which differ from the compounds Ial.l to Ial.342 or Ibl.l to Ibl.342 in that R 9 g means "5-methyl".
Ia3 Ib3Ia3 Ib3
Die Verbindungen der Formel Ia4 und Ib4, insbesondere die Verbindungen Ia4.1 bis Ia4.342 und die Verbindungen Ib4.1 bis Ib4.342, die sich von den Verbindungen lal.l bis Ial.342 bzw. Ibl.l bis Ibl.342 dadurch unterscheiden, daß (R9 q) "4 , 4-Dimethyl" bedeutet.The compounds of the formulas Ia4 and Ib4, in particular the compounds Ia4.1 to Ia4.342 and the compounds Ib4.1 to Ib4.342, which differ from the compounds Ial.l to Ial.342 or Ibl.l to Ibl.342 distinguish in that (R 9 q ) means "4, 4-dimethyl".
Ia4 Ib4Ia4 Ib4
Die Verbindungen der Formel Ia5 und Ib5, insbesondere die Verbindungen Ia5.1 bis Ia5.342 und die Verbindungen Ib5.1 bis Ib5.342, die sich von den Verbindungen lal.l bis Ial.342 bzw. Ibl.l bis Ibl.342 dadurch unterscheiden, daß (R9)q "6, 6 -Dimethyl" bedeutet. The compounds of the formula Ia5 and Ib5, in particular the compounds Ia5.1 to Ia5.342 and the compounds Ib5.1 to Ib5.342, which differ from the compounds Ial.l to Ial.342 or Ibl.l to Ibl.342 distinguish in that (R 9 ) q means "6, 6 -dimethyl".
Ia5 Ib5Ia5 Ib5
Die Verbindungen der Formel Ia6 und Ib6, insbesondere die Verbindungen Iaβ.l bis Ia6.342 und die Verbindungen Ibβ.l bisThe compounds of the formula Ia6 and Ib6, in particular the compounds Iaβ.l to Ia6.342 and the compounds Ibβ.l to
Ib6.342, die sich von den Verbindungen lal.l bis Ial.342 bzw. Ibl.l bis Ibl.342 dadurch unterscheiden, daß (R9)q "4,4,6,6 -Tetramethyl -5 -oxo" bedeutet.Ib6.342, which differ from the compounds Ial.l to Ial.342 or Ibl.l to Ibl.342 in that (R 9 ) q means "4,4,6,6-tetramethyl -5-oxo" .
Ia6 Ib6Ia6 Ib6
Die Verbindungen der Formel Ia7 und Ib7, insbesondere die Verbindungen Ia7.1 bis Ia7.342 und die Verbindungen Ib7.1 bis Ib7.342, die sich von den Verbindungen lal.l bis Ial.342 bzw. Ibl.l bis Ibl.342 dadurch unterscheiden, daß (R9)q "6-Methyl" bedeutet.The compounds of the formulas Ia7 and Ib7, in particular the compounds Ia7.1 to Ia7.342 and the compounds Ib7.1 to Ib7.342, which differ from the compounds Ial.l to Ial.342 or Ibl.l to Ibl.342 differ in that (R 9 ) q means "6-methyl".
Ia7 Ib7Ia7 Ib7
Die Verbindungen der Formel Ia8 und Ib8, insbesondere die Verbindungen Ia8.1 bis Ia8.342 und die Verbindungen Ibδ.l bis Ib8.342, die sich von den Verbindungen lal.l bis Ial.342 bzw. Ibl.l bis Ibl.342 dadurch unterscheiden, daß (R9)q " 5 -Hydroxy- 4 , 4,6, 6 - tetramethyl" bedeutet. la. Ib8The compounds of the formula Ia8 and Ib8, in particular the compounds Ia8.1 to Ia8.342 and the compounds Ibδ.l to Ib8.342, which differ from the compounds Ial.l to Ial.342 or Ibl.l to Ibl.342 distinguish in that (R 9 ) q means "5-hydroxy-4, 4,6, 6 - tetramethyl". la. Ib8
Ebenso außerordentlich bevorzugt sind die Verbindungen der Formel Ia9 und Ib9 (≡ I mit X = S02 , R1 = CH3 , R3 = H und 1 = 0), insbesondere die Verbindungen Ia9.1 bis Ia9.456 und Ib9.1 bis Ib9.456, wobei die Restedefinitionen R1 bis R9, 1 und q nicht nur in Kombination miteinander, sondern auch jeweils für sich allein betrachtet für die erfindungsgemäßen Verbindungen eine besondere Bedeutung haben. Also particularly preferred are the compounds of the formulas Ia9 and Ib9 (≡ I with X = S0 2 , R 1 = CH 3 , R 3 = H and 1 = 0), in particular the compounds Ia9.1 to Ia9.456 and Ib9.1 to Ib9.456, where the radical definitions R 1 to R 9 , 1 and q are of particular importance not only in combination with one another, but also in isolation for the compounds according to the invention.
Ia9 Ib9Ia9 Ib9
Tabelle 2Table 2
Desweiteren sind die Verbindungen IalO und IblO, insbesondere die Verbindungen IalO.l bis IalO.456 und IblO.l bis IblO.456, die sich von den Verbindungen Ia9.1 bis Ia9.456 bzw. Ib9.1 bis Ib9.456 dadurch unterscheiden, daß R1 für Chlor steht, außerordentlich bevorzugt. Furthermore, the compounds IalO and IblO, in particular the compounds IalO.l to IalO.456 and IblO.l to IblO.456, which differ from the compounds Ia9.1 to Ia9.456 or Ib9.1 to Ib9.456 that R 1 represents chlorine is extremely preferred.
IalO IblO Ebenso sind die Verbindungen lall und Ibll, insbesondere die Verbindungen Iall.l bis lall.456 und Ibll.l bis Ibll.456, die sich von den Verbindungen Ia9.1 bis Ia9.456 bzw. Ib9.1 bis Ib9.456 dadurch unterscheiden, daß R1 für Methoxy steht, außerordentlich bevorzugt.IalO IblO Likewise, the compounds Iall and Ibll, in particular the compounds Iall.l to Iall.456 and Ibll.l to Ibll.456, which differ from the compounds Ia9.1 to Ia9.456 or Ib9.1 to Ib9.456 differ in that R 1 is methoxy, extremely preferred.
lall Ibll Illl
Weiterhin außerordentlich bevorzugt sind die Verbindungen la, insbesondere die Verbindungen Ial bis lall, sowie die jeweils ge- nannten Ausführungsformen.The compounds Ia, in particular the compounds Ial to Iall, and the embodiments mentioned in each case are also extremely preferred.
Die Cyclohexenondioxothiochromanoyl -Derivate der Formel I sind auf verschiedene Art und Weise erhältlich, beispielsweise nach folgenden Verfahren:The cyclohexenone dioxothiochromanoyl derivatives of the formula I can be obtained in various ways, for example by the following processes:
A. Darstellung von Verbindungen der Formel I mit R8 = Halogen durch Umsetzung von Cyclohexandion-Derivaten der Formel III mit Halogenierungsmitteln:A. Preparation of compounds of the formula I with R 8 = halogen by reacting cyclohexanedione derivatives of the formula III with halogenating agents:
Halogenierungs ■ la und/oder Ib mittel (mit R8 = Halogen)Halogenation ■ la and / or Ib medium (with R 8 = halogen)
Als Halogenierungsmittel eignen sich beispielsweise Phosgen, Diphosgen, Triphosgen, Thionylchlorid, Oxalylchlorid, Phosphoroxychlorid, Phosphorpentachlorid, Mesylchlorid, Chlormethylen-N, N-dimethylammoniumchlorid, Oxylylbromid, Phosphoroxybromid etc. Examples of suitable halogenating agents are phosgene, diphosgene, triphosgene, thionyl chloride, oxalyl chloride, phosphorus oxychloride, phosphorus pentachloride, mesyl chloride, chloromethylene-N, N-dimethylammonium chloride, oxylyl bromide, phosphorus oxybromide etc.
Die AusgangsVerbindungen werden in der Regel im äquimolaren Verhältnis eingesetzt. Es kann aber auch von Vorteil sein, die eine oder andere Komponente im Überschuß einzusetzen.The output connections are usually used in an equimolar ratio. However, it can also be advantageous to use one or the other component in excess.
Als Lösungsmittel kommen z.B. chlorierte Kohlenwasserstoffe, wie Methylenchlorid oder 1, 2 -Dichlorethan, aromatische Kohlenwasserstoffe, z.B. Toluol, Xylol oder Chlorbenzol, polare aprotische Lösungsmittel, wie Acetonitril, Dimethylform- amid oder Dimethylsulfoxid oder Gemische hiervon in Betracht. Die Reaktion kann auch in Substanz durchgeführt werden.Examples of solvents are chlorinated hydrocarbons such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons e.g. Toluene, xylene or chlorobenzene, polar aprotic solvents, such as acetonitrile, dimethylformamide or dimethyl sulfoxide, or mixtures thereof. The reaction can also be carried out in bulk.
In der Regel liegt die Reaktionstemperatur im Bereich von 0°C bis zur Höhe des Siedepunktes des Reaktionsgemisches.As a rule, the reaction temperature is in the range from 0 ° C. to the boiling point of the reaction mixture.
Die Aufarbeitung kann in an sich bekannter Weise zum Produkt hin erfolgen.The product can be worked up in a manner known per se.
Darstellung von Verbindungen der Formel I mit R8 = OR10, OSO2R11, OPORι:LR12 oder OPSR11R12 durch Umsetzung von Cyclohe- xandion-Derivaten der Formel III mit Alkylierungs - , Sulfony- lierungs- bzw. Phosphonylierungsmitteln IVα, IVß, IVγ bzw. IVδ.Preparation of compounds of the formula I with R 8 = OR 10 , OSO 2 R 11 , OPOR ι: L R 12 or OPSR 11 R 12 by reacting cyclohexanedione derivatives of the formula III with alkylation, sulfonation or Phosphonylating agents IVα, IVß, IVγ and IVδ.
l-RlO IVα l -R lO IVα
R12 R 12
III oder Ll-PSRllRl2 ιvδ III or L l -PSR ll R l2 ιvδ
L1 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. Die Verbindungen der Formel IVα, IVß, IVγ oder IVδ können direkt eingesetzt werden wie z. B. im Fall der Carbonsäurehalogenide oder in situ erzeugt werden, z. B. aktivierte Carbon- säuren (mit Carbonsäure und Dicyclohexylcarbodiimid etc.) .L 1 stands for a nucleophilically displaceable leaving group, such as halogen, e.g. B. chlorine or bromine, hetaryl, e.g. B. imidazolyl, carboxylate, e.g. B. acetate, or sulfonate, e.g. B. mesylate or triflate etc. The compounds of formula IVα, IVß, IVγ or IVδ 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.).
Die Ausgangsverbindungen werden in der Regel im äquimolaren Verhältnis eingesetzt. Es kann aber auch von Vorteil sein, die eine oder andere Komponente im Überschuß einzusetzen.The starting compounds are generally used in an equimolar ratio. However, it can also be advantageous to use one or the other component in excess.
Gegebenenfalls kann es von Vorteil sein, die Umsetzungen in Gegenwart einer Base durchzuführen. Die Reaktanden und die Base werden dabei zweckmäßigerweise in äquimolaren Mengen eingesetzt. Ein Überschuß der Base z.B. 1,5 bis 3 Moläquivalente kann unter Umständen vorteilhaft sein.It may be advantageous to carry out the reactions in the presence of a base. The reactants and the base are expediently used in equimolar amounts. An excess of the base e.g. 1.5 to 3 molar equivalents can be advantageous under certain circumstances.
Als Basen eignen sich tertiäre Alkylamine, wie Triethylamin, aromatische Amine, wie Pyridin, Alkalimetallcarbonate, z.B. Natriumcarbonat oder Kaliumcarbonat, Alkalimetallhydrogen- carbonate, wie Natriumhydrogencarbonat und Kaliu hydrogen- carbonat, Alkalimetallalkoholate wie Natriummethanolat,Suitable bases are tertiary alkyl amines such as triethylamine, aromatic amines such as pyridine, alkali metal carbonates, e.g. Sodium carbonate or potassium carbonate, alkali metal hydrogen carbonates, such as sodium hydrogen carbonate and potassium hydrogen carbonate, alkali metal alcoholates such as sodium methoxide,
Natriumethanolat, Kalium- tert. -butanolat oder Alkalimetallhydride, z.B. Natriumhydrid. Bevorzugt verwendet werden Triethylamin oder Pyridin.Sodium ethanolate, potassium tert. butanolate or alkali metal hydrides, e.g. Sodium hydride. Triethylamine or pyridine are preferably used.
Als Lösungsmittel kommen z.B. chlorierte Kohlenwasserstoffe, wie Methylenchlorid oder 1, 2 -Dichlorethan, aromatische Kohlenwasserstoffe, z.B. Toluol, Xylol oder Chlorbenzol, Ether, wie Diethylether, Methyl- tert . -butylether, Tetrahydro- furan oder Dioxan, polare aprotische Lösungsmittel, wie Acetonitril, Dimethylformamid oder Dimethylsulfoxid oderExamples of solvents are chlorinated hydrocarbons such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons e.g. Toluene, xylene or chlorobenzene, ethers such as diethyl ether, methyl tert. -butyl ether, tetrahydrofuran or dioxane, polar aprotic solvents such as acetonitrile, dimethylformamide or dimethyl sulfoxide or
Ester, wie Essigsäureethylester, oder Gemische hiervon in Betracht.Esters, such as ethyl acetate, or mixtures thereof.
In der Regel liegt die Reaktionstemperatur im Bereich von 0°C bis zur Höhe des Siedepunktes des Reaktionsgemisches.As a rule, the reaction temperature is in the range from 0 ° C. to the boiling point of the reaction mixture.
Die Aufarbeitung kann in an sich bekannter Weise zum Produkt hin erfolgen.The product can be worked up in a manner known per se.
Darstellung von Verbindungen der Formel I mit R8 = OR10, SR10, POR1:LR12, NR13R14, ONR14R14, N-gebundenes Heterocyclyl oder O- (N-gebundenes Heterocyclyl) durch Umsetzung von Verbindungen der Formel I mit R8 = Halogen, OS02R1:L (Iα) mit Verbindungen der Formel Vα, Vß, Vγ, Vδ, Vε, Vη oder Vθ, gegebenenfalls in Gegenwart einer Base oder unter vorangehender Salzbildung. HÖR 1100 V Vαα oder la und/oder Ib (mit + R8 = OR10 SR10 i Ü Z n. OSO*», H HSSHR.1O0 V Vßß→— P∞llR». «. oder 0NRiR14 N-gebundenesRepresentation of compounds of formula I with R 8 = OR 10 , SR 10 , POR 1: L R 12 , NR 13 R 14 , ONR 14 R 14 , N-linked heterocyclyl or O- (N-linked heterocyclyl) by reacting compounds of the formula I with R 8 = halogen, OS0 2 R 1: L (Iα) with compounds of the formula Vα, Vß, Vγ, Vδ, Vε, Vη or Vθ, optionally in the presence of a base or with previous salt formation. HÖR 1100 V Vαα or la and / or Ib (with + R 8 = OR 10 SR 10 i Ü Z n . OSO * », H HSSHR. 1O0 VV ß ß → - P∞ ll R » . « . Or 0NR i R 14 N-linked
HPOR1:LR12 vγ Heterocyclyl oder oder 0- (N-gebundenes Heterocyclyl) )HPOR 1: L R 12 vγ heterocyclyl or or 0- (N-linked heterocyclyl))
HNR13R14 vδ oderHNR 13 R 14 vδ or
HONR14R14 vε oderHONR 14 R 14 vε or
H (N- gebundenes Vη Heterocyclyl ) oderH (N-linked Vη heterocyclyl) or
HO (N-gebundenes Vθ Heterocyclyl)HO (N-linked Vθ heterocyclyl)
Die Ausgangsverbindungen werden in der Regel im äquimolaren Verhältnis eingesetzt. Es kann aber auch von Vorteil sein, die eine oder andere Komponente im Überschuß einzusetzen.The starting compounds are generally used in an equimolar ratio. However, it can also be advantageous to use one or the other component in excess.
Gegebenenfalls kann es von Vorteil sein, die Umsetzungen in Gegenwart einer Base durchzuführen. Die Reaktanden und die Base werden dabei zweckmäßigerweise in äquimolaren Mengen eingesetzt. Ein Überschuß der Base z.B. 1,5 bis 3 Moläquivalente, bezogen auf la und/oder Ib (mit R8 = Halogen) kann unter Umständen vorteilhaft sein.It may be advantageous to carry out the reactions in the presence of a base. The reactants and the base are expediently used in equimolar amounts. An excess of the base, for example 1.5 to 3 molar equivalents, based on la and / or Ib (with R 8 = halogen) can be advantageous under certain circumstances.
Als Basen eignen sich tertiäre Alkylamine, wie tertiäreSuitable bases are tertiary alkyl amines, such as tertiary
Alkylamine, wie Pyridin, Alkalimetallcarbonate, z.B. Natrium- carbonat oder Kaliumcarbonat, Alkalimetallhydrogencarbonate, wie Natriumhydrogencarbonat und Kaliumhydrogencarbonat, Alkalimetallalkoholate wie Natriummethanolat, Natrium- methanolat, Kalium- tert. -butanolat oder Alkalimetallhydride, z.B. Natriumhydrid. Bevorzugt verwendet werden Natriumhydroxid oder Kalium- tert . -butylat.Alkyl amines such as pyridine, alkali metal carbonates, e.g. Sodium carbonate or potassium carbonate, alkali metal bicarbonates such as sodium bicarbonate and potassium bicarbonate, alkali metal alcoholates such as sodium methoxide, sodium methoxide, potassium tert. butanolate or alkali metal hydrides, e.g. Sodium hydride. Sodium hydroxide or potassium tert are preferably used. -butylate.
Als Lösungsmittel kommen z.B. chlorierte Kohlenwasserstoffe, wie Methylenchlorid oder 1, 2 -Dichlorethan, aromatischeExamples of solvents are chlorinated hydrocarbons, such as methylene chloride or 1,2-dichloroethane, aromatic
Kohlenwasserstoffe, z.B. Toluol, Xylol oder Chlorbenzol, Ether, wie Diethylether, Methyl- tert . -butylether, Tetrahydro- furan oder Dioxan, polare aprotische Lösungsmittel, wie Acetonitril, Dimethylformamid oder Dimethylsulfoxid oder Ge- mische hiervon in Betracht. In der Regel liegt die Reaktionstemperatur im Bereich von 0°C bis zur Höhe des Siedepunktes des Reaktionsgemisches.Hydrocarbons, for example 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 mixtures thereof. As a rule, the reaction temperature is in the range from 0 ° C. to the boiling point of the reaction mixture.
Die Aufarbeitung kann in an sich bekannter Weise zum Produkt hin erfolgen.The product can be worked up in a manner known per se.
D. Darstellung von Verbindungen der Formel I mit R8 = SOR11, S02Rι:L durch Umsetzung von Verbindungen der Formel I mit R8 = SR11 (Iß) mit einem Oxidationsmittel .D. Preparation of compounds of the formula I with R 8 = SOR 11 , S0 2 R ι: L by reacting compounds of the formula I with R 8 = SR 11 (Iß) with an oxidizing agent.
la und/oder Ib Oxidationsmittel Ia und/oder Ib l a and / o d er Ib oxidizing agent Ia and / or Ib
(mit R8 = SR11) ► (mit R8 = SORll, SOaR11)(with R 8 = SR 11 ) ► (with R 8 = SOR ll , SOaR 11 )
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 Ausgangsverbindungen werden in der Regel im äquimolaren Verhältnis eingesetzt. Es kann aber auch von Vorteil sein, die eine oder andere Komponente im Überschuß einzusetzen.The starting compounds are generally used in an equimolar ratio. However, it can also be advantageous to use one or the other component in excess.
Als Lösungsmittel kommen z.B. chlorierte Kohlenwasserstoffe, wie Methylenchlorid oder 1, 2-Dichlorethan, aromatische Kohlenwasserstoffe, z.B. Toluol, Xylol oder Chlorbenzol, Ether, wie Diethylether, Methyl-tert. -butylether, Tetrahydro- furan oder Dioxan, polare aprotische Lösungsmittel, wie Acetonitril, Dimethylformamid oder Ester, wie Essigsäure- ethylester, oder Gemische hiervon in Betracht.Examples of solvents are chlorinated hydrocarbons such as methylene chloride or 1,2-dichloroethane, aromatic hydrocarbons e.g. Toluene, xylene or chlorobenzene, ethers such as diethyl ether, methyl tert. -butyl ether, tetrahydrofuran or dioxane, polar aprotic solvents such as acetonitrile, dimethylformamide or esters such as ethyl acetate, or mixtures thereof.
In der Regel liegt die Reaktionstemperatur im Bereich von 0°C bis zur Höhe des Siedepunktes des Reaktionsgemisches.As a rule, the reaction temperature is in the range from 0 ° C. to the boiling point of the reaction mixture.
Die Aufarbeitung kann in an sich bekannter Weise zum Produkt hin erfolgen.The product can be worked up in a manner known per se.
In Abhängigkeit von den Reaktionsbedinungen können die Verbindun- gen la, Ib oder Gemische hiervon gebildet werden. Letztere können durch klassische Trennmethoden, wie z.B. Kristallisation, Chromatographie etc., getrennt werden.Depending on the reaction conditions, compounds la, Ib or mixtures thereof can be formed. The latter can be separated using classic separation methods, e.g. Crystallization, chromatography, etc., are separated.
Die Cyclohexandion-Derivate der Formel III sind bekannt oder kön- nen nach an sich bekannten Verfahren hergestellt werden (z.B.The cyclohexanedione derivatives of the formula III are known or can be prepared by processes known per se (e.g.
DE 19 532 311) . Beispielsweise durch Umsetzung von Cyclohexanonen der Formel VI mit einer aktivierten Benzoesäure Vlla oder einer Benzoesaure VIIb, die vorzugsweise in situ aktiviert wird, zu dem Acylierungsprodukt und anschließende Umlagerung.DE 19 532 311). For example, by reacting cyclohexanones of the formula VI with an activated benzoic acid Vlla or one Benzoic acid VIIb, which is preferably activated in situ, to the acylation product and subsequent rearrangement.
VI VIIaVI VIIa
IIIIII
L2 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.L 2 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 Benzoesaure Vlla kann direkt eingesetzt werden, wie im Fall der Benzoylhalogenide oder in situ erzeugt werden, z.B. mit Dicyclohexylcarbodiimid, Triphenylphosphin/Azodicarbon- säureester, 2-Pyridindisulfid/Triphenylphosphin, Carbonyldi- imidazol etc.The activated Vlla benzoic acid 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 Acylierungsreaktion in Gegenwart einer Base auszuführen. Die Reaktanden und die Hilfsbase werden dabei zweckmäßigerweise in äquimolaren Mengen eingesetzt. Ein geringer Überschuß der Hilfsbase z.B. 1,2 bis 1,5 Moläquivalente, bezogen auf VII, 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. 1.2 to 1.5 molar equivalents, based on VII, can be advantageous under certain circumstances.
Als Hilfsbasen eignen sich tertiäre Alkylamine, Pyridin oder Alkalimetallcarbonate. Als Lösungsmittel können z.B. chlorierte Kohlenwasserstoffe, wie Methylenchlorid oder 1, 2-Dichlorethan, aromatische Kohlenwasserstoffe, wie Toluol, Xylol oder Chlorbenzol, Ether, wie Diethylether, Methyl-tert . -butylether, Tetra- hydrofuran oder Dioxan, polare aprotische Lösungsmittel, wie Acetonitril, Dimethylformamid oder Dimethylsulfoxid oder Ester wie Essigsäureethylester oder Gemische hiervon verwendet werden.Tertiary alkyl amines, pyridine or alkali metal carbonates are suitable as auxiliary bases. Examples of solvents which can be used are 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, tetra- hydrofuran or dioxane, polar aprotic solvents such as acetonitrile, dimethylformamide or dimethyl sulfoxide or esters such as ethyl acetate or mixtures thereof.
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 Umlagerung 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 rearrangement without further purification.
Die Umlagerung der Ester zu den Verbindungen der Formel III erfolgt zweckmäßigerweise bei Temperaturen von 20 bis 100°C in einem Lösungsmittel und in Gegenwart einer Base sowie gegebenenfalls mit Hilfe einer Cyanoverbindung als Katalysator.The rearrangement of the esters to the compounds of the formula III 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 catalyst.
Als Lösungsmittel können z.B. Acetonitril, Methylenchlorid, 1, 2-Dichlorethan, Dioxan, Essigsäureethylester, Toluol oder Gemische hiervon verwendet werden. Bevorzugte Lösungsmittel sind Acetonitril und Dioxan.As a solvent e.g. Acetonitrile, methylene chloride, 1, 2-dichloroethane, dioxane, ethyl acetate, toluene or mixtures thereof can be used. Preferred solvents are acetonitrile and dioxane.
Geeignete Basen sind tertiäre Amine wie Triethylamin, aromatische Amine wie Pyridin oder Alkalicarbonate, wie Natriumcarbonat oder Kaliumcarbonat, die vorzugsweise in äquimolarer Menge oder bis zu einem vierfachen Überschuß, bezogen auf den Ester, eingesetzt werden. Bevorzugt werden Triethylamin oder Alkalicarbonat verwendet, vorzugsweise in doppelt äquimolaren Verhältnis in Bezug auf den Ester.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 Natrium- cyanid 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 Tri- methylsilylcyanid, z.B. in einer Menge von 5 bis 15, vorzugsweise 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 10 mol 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 Kaliumcarbonat- lösung extrahiert werden. Die wäßrige Phase wird angesäuert und der sich bildende Niederschlag abgesaugt und/oder mit Methylenchlorid oder Essigsäureethylester extrahiert, getrocknet und ein- 5 geengt.Working up can be carried out in a manner known per se. The reaction mixture is acidified, for example with dilute mineral acid, such as 5% hydrochloric acid or sulfuric acid, and extracted with an organic solvent, for example methylene chloride or ethyl acetate. The organic extract can contain 5-10% Alkali carbonate solution, for example sodium carbonate or potassium carbonate solution. The aqueous phase is acidified and the precipitate that forms is filtered off with suction and / or extracted with methylene chloride or ethyl acetate, dried and concentrated.
Die Benzoylhalogenide der Formel Vlla (mit L2 = CI, Br) können auf an sich bekannte Art und Weise durch Umsetzung der Benzoesäuren der Formel Vllb mit Halogenierungsreagentien wie Thionylchlorid, 10 Thionylbromid, Phosgen, Diphosgen, Triphosgen, Oxalylchlorid, Oxalylbromid hergestellt werden.The benzoyl halides of the formula VIIa (with L 2 = CI, Br) can be prepared in a manner known per se by reacting the benzoic acids of the formula VIIb with halogenating reagents such as thionyl chloride, 10 thionyl bromide, phosgene, diphosgene, triphosgene, oxalyl chloride, oxalyl bromide.
Die Benzoesäuren der Formel Vllb können in bekannter Weise durch saure oder basische Hydrolyse aus den entsprechenden Estern her- 15 gestellt werden.The benzoic acids of the formula VIIIb can be prepared in a known manner from the corresponding esters by acidic or basic hydrolysis.
Herstellungsbeispiele :Manufacturing examples:
1- Chlor -2 - (8 -chlor-4 , 4-dimethyl-l, l-dioxothiochroman-7 -yl) -carbo- 20 nyl-cyclohex-l-en-3 -on (Verbindung 3.2)1- chlorine -2 - (8-chloro-4, 4-dimethyl-l, l-dioxothiochroman-7 -yl) -carbo- 20 nyl-cyclohex-l-en-3 -one (compound 3.2)
Stufe a) 3 - (3-Methyl-2-butenylthio) -2-chlor-benzoesäuremethyl- esterStep a) 3 - (3-methyl-2-butenylthio) -2-chloro-benzoic acid methyl ester
25 Zu 80.3 g (0.27 mol) 3-Thio-2-chlor-benzoesäuremethylester in25 To 80.3 g (0.27 mol) of methyl 3-thio-2-chloro-benzoate in
500 ml Aceton wurden 37.2 g (0.27 mol) Kaliumcarbonat gegeben und 40.2 g (0.27 mol) 3-Methyl -2 -butenylbromid getropft und 3 Stunden bei Raumtemperatur gerührt. Nach Abdestillieren des Lösungsmittels wurde der Rückstand in Wasser/Essigsäureethylester aufgenom-37.2 g (0.27 mol) of potassium carbonate were added to 500 ml of acetone and 40.2 g (0.27 mol) of 3-methyl-2-butenyl bromide were added dropwise and the mixture was stirred at room temperature for 3 hours. After the solvent had been distilled off, the residue was taken up in water / ethyl acetate.
30 men, die organische Phase getrocknet, abfiltriert und eingeengt. Das zurückbleibende braune Öl wurde über Kieselgel mit Essigsäu- reethylester/Cyclohexan chromatographiert . Ausbeute : 63.4 g (86.9%) gelbes Öl. iH-NMR (CDC13, δ in ppm) : 7.52 (d, 1H) ; 7.32 (d , lH) ; 7 . 26 ( t , lH30 men, the organic phase dried, filtered off and concentrated. The remaining brown oil was chromatographed on silica gel with ethyl acetate / cyclohexane. Yield: 63.4 g (86.9%) yellow oil. iH NMR (CDC1 3 , δ in ppm): 7.52 (d, 1H); 7.32 (d, 1H); 7. 26 (t, lH
35 5.26 (m,lH); 3.90 ( S , 3H) , 3 . 49 (d , 2H35 5.26 (m, 1H); 3.90 (S, 3H), 3. 49 (d. 2H
2.60 (s,3H); 1.70 ( s , 3H) ; 1 . 59 ( s , 3H2.60 (s, 3H); 1.70 (s, 3H); 1 . 59 (s, 3H
Stufe b) 8-Chlor-4 , 4-dimethylthiochroman-7-carbonsäuremethylesterStep b) 8-chloro-4, 4-dimethylthiochroman-7-carboxylic acid methyl ester
40 63.4 g (0.234 mol) 3- (3-Methyl -2 -butenylthio) -2-chlor-benzoesäu- remethylester wurden in 600 ml Methylenchlorid gelöst und bei 0°C 94 g (0.94 mol) konz . Schwefelsäure zugetropft. Nach 30 Minuten Rühren wurde diese Lösung auf Eiswasser gegeben, die organische Phase abgetrennt, getrocknet und eingeengt. Das entstandene40 63.4 g (0.234 mol) of 3- (3-methyl -2-butenylthio) -2-chloro-benzoate were dissolved in 600 ml of methylene chloride and 94 g (0.94 mol) of conc. Added dropwise sulfuric acid. After stirring for 30 minutes, this solution was poured onto ice water, the organic phase was separated off, dried and concentrated. The resulting
45 orange Öl (57.1 g) wurde ohne weitere Reinigung in der nächsten Stufe eingesetzt. !H-NMR ( CDC13 , δ in ppm) : 7 . 40 ( d, lH) ; 7 . 32 ( d , 1H) ; 3 . 90 ( s , 3H) ;45 orange oil (57.1 g) was used in the next step without further purification. ! H NMR (CDC1 3 , δ in ppm): 7. 40 (d, 1H); 7. 32 (d, 1H); 3rd 90 (s, 3H);
3 . 05 (m, 2H) ; 1 . 98 (m, lH) ; 1 . 32 ( s , 6H) .3rd 05 (m, 2H); 1 . 98 (m, 1H); 1 . 32 (s, 6H).
Stufe c) 8-Chlor-4, 4-dimethylthiochroman-7-carbonsäureStep c) 8-chloro-4, 4-dimethylthiochroman-7-carboxylic acid
53.1 g des rohen 8-Chlor-4 , 4-dimethylthiochroman-7-carbonsäure- methylester wurden in 500 ml eines 1 : 1 Wasser/Methanol -Gemisches vorgelegt und 11.8 g (0.29 mol) Natriumhydroxid zugegeben. Die Lösung wurde dann drei Stunden unter Rückfluß erhitzt. Nach Abkühlen wurde das organische Lösungsmittel entfernt, der Rückstand mit 200 ml Wasser verdünnt und unter Kühlung mit konz . Salzsäure sauer gestellt. Der ausgefallene Niederschlag wird abgesaugt, mit Essigsäure und Wasser gewaschen und getrocknet. Ausbeute: 27.1 g Schmelzpunkt: 227°C53.1 g of the crude 8-chloro-4, 4-dimethylthiochroman-7-carboxylic acid methyl ester were placed in 500 ml of a 1: 1 water / methanol mixture and 11.8 g (0.29 mol) sodium hydroxide were added. The solution was then refluxed for three hours. After cooling, the organic solvent was removed, the residue was diluted with 200 ml of water and cooled with conc. Hydrochloric acid acidified. The precipitate is filtered off, washed with acetic acid and water and dried. Yield: 27.1 g melting point: 227 ° C
Stufe d) 8-Chlor-4 , 4-dimethyl-l, l-dioxothiochroman-7-carbonsäureStep d) 8-chloro-4, 4-dimethyl-l, l-dioxothiochroman-7-carboxylic acid
27.1 g (0.106 mol) 8-Chlor-4 , 4-dimethylthiochroman-7-carbonsäure wurden in 200 ml Essigsäure gelöst und eine Spatelspitze Natriumwolframat zugegeben. Bei 50-60°C wurden 26.3 g (0.23 mol) 30%-iges Wasserstoffperoxid zugetropft, zwei Stunden bei 50°C nachgerührt, in Eiswasser eingerührt, die ausgefallenen weißen Nadeln abfiltriert, mit Wasser gewaschen und getrocknet. Ausbeute: 26.0 g (85.3%) Schmelzpunkt: 252°C27.1 g (0.106 mol) of 8-chloro-4, 4-dimethylthiochroman-7-carboxylic acid were dissolved in 200 ml of acetic acid and a spatula tip of sodium tungstate was added. 26.3 g (0.23 mol) of 30% hydrogen peroxide were added dropwise at 50-60 ° C., the mixture was stirred at 50 ° C. for two hours, stirred into ice water, the precipitated white needles were filtered off, washed with water and dried. Yield: 26.0 g (85.3%) melting point: 252 ° C
Stufe e) 8-Chlor-4, 4-dimethyl-l, l-dioxothiochroman-7 -carbonsäu- rechloridStep e) 8-chloro-4, 4-dimethyl-l, l-dioxothiochroman-7-carboxylic acid chloride
26.0 g (0.09 mol) 8-Chlor-4 , 4-dimethyl-l, 1-dioxothio- chroman-7-carbonsäure wurden in 200 ml Toluol gelöst und drei Tropfen Dimethylformamid zugegeben. Nach Zutropfen von 11.8 g (0.099 mol) Thionylchlorid wurde drei Stunden zum Rückfluß er- hitzt und dann das Lösungsmittel entfernt. Man erhielt ein farbloses Öl (Ausbeute 27.5 g) , das direkt weiter eingesetzt wurde.26.0 g (0.09 mol) of 8-chloro-4, 4-dimethyl-l, 1-dioxothio-chroman-7-carboxylic acid were dissolved in 200 ml of toluene and three drops of dimethylformamide were added. After the dropwise addition of 11.8 g (0.099 mol) of thionyl chloride, the mixture was heated under reflux for three hours and then the solvent was removed. A colorless oil was obtained (yield 27.5 g), which was used directly.
Stufe f) 2- (8-Chlor-4, 4-dimethyl-l, l-dioxothiochroman-7-yl) -car- bonyl-1, 3-cyclohexandionStep f) 2- (8-chloro-4, 4-dimethyl-l, l-dioxothiochroman-7-yl) carbonyl-1, 3-cyclohexanedione
7.8 g (0.07 mol) Cyclohexan-1, 3-dion und 21.2 g (0.07 mol) Triethylamin wurden in 50 ml Acetonitril gelöst und 20.0 g (0.07 mol) 8-Chlor-4, 4-dimethyl-l, l-dioxothiochroman-7-carbonsäure- chlorid in 200 ml Acetonitril zugetropft. Nach zwei Stunden Rüh- ren bei Raumtemperatur wurden 0.5 ml Trimethylsilylcyanid zugetropft, drei Stunden auf 40 °C erwärmt, das Lösungsmittel entfernt, der Rückstand in 2%-iger Natriumhydrogencarbonat-Lösung aufgenommen und jeweils einmal mit Essigsäureethylester bzw. Diethylether extrahiert. Die Wasserphase wurde dann mit konz . Salzsäure auf pH 3 gestellt, der Niederschlag abfiltriert, mit Wasser gewaschen und getrocknet. Ausbeute: 20.3 g (80.3 %) cremefarbene Kristalle Schmelzpunkt: 165°C7.8 g (0.07 mol) of cyclohexane-1, 3-dione and 21.2 g (0.07 mol) of triethylamine were dissolved in 50 ml of acetonitrile and 20.0 g (0.07 mol) of 8-chloro-4, 4-dimethyl-l, l-dioxothiochroman 7-carboxylic acid chloride added dropwise in 200 ml of acetonitrile. After stirring for two hours at room temperature, 0.5 ml of trimethylsilyl cyanide was added dropwise, the mixture was warmed to 40 ° C. for three hours, the solvent was removed and the residue in 2% sodium hydrogen carbonate solution added and extracted once each with ethyl acetate or diethyl ether. The water phase was then concentrated. Hydrochloric acid adjusted to pH 3, the precipitate filtered off, washed with water and dried. Yield: 20.3 g (80.3%) of cream-colored crystals. Melting point: 165 ° C.
Stufe g) l-Chlor-2- (8-chlor-4, 4-dimethyl-l, 1-dioxothio- chroman-7-yl) -carbonyl-cyclohex-l-en-3-on (Verbin- düng 3.2)Stage g) l-chloro-2- (8-chloro-4, 4-dimethyl-l, 1-dioxothio-chroman-7-yl) -carbonyl-cyclohex-l-en-3-one (compound 3.2)
2.0 g (5.2 mmol) 2- (8-Chlor-4 , 4-dimethyl-l, 1-dioxothio- chroman-7 -yl) -carbonyl-1, 3-cyclohexandion wurden in 30 ml Methylenchlorid gelöst, 2.2 g (17.3 mmol) Oxalylchlorid und 2 Tropfen Dimethylformamid zugegeben. Nach 1 Stunde Rühren bei 25°C wurde das Lösungsmittel entfernt. Man erhielt 2.1 g farblose Kristalle.2.0 g (5.2 mmol) 2- (8-chloro-4, 4-dimethyl-l, 1-dioxothio-chroman-7 -yl) -carbonyl-1, 3-cyclohexanedione were dissolved in 30 ml methylene chloride, 2.2 g (17.3 mmol) of oxalyl chloride and 2 drops of dimethylformamide were added. After stirring at 25 ° C for 1 hour, the solvent was removed. 2.1 g of colorless crystals were obtained.
2- (8-Chlor-4 , 4-dimethyl-l, l-dioxothiochroman-7 -yl) -carbonyl-1- (4- chlorphenylthio) -cyclohex-l-en-3-on (Verbindung 3.6)2- (8-chloro-4, 4-dimethyl-l, l-dioxothiochroman-7 -yl) carbonyl-1- (4-chlorophenylthio) cyclohex-l-en-3-one (compound 3.6)
0.8 g (2 mmol) l-Chlor-2- (8-chlor-4 , 4-dimethyl-l, 1-dioxothio- chroman-7 -yl) -carbonyl-cyclohex-l-en-3-on wurden in 10 ml Tetra- hydrofuran gelöst, 0.29 g (2 mmol) 4-Chlorthiophenol und 0.22 g (2.2 mmol) Triethylamin zugetropft. Nach 2 Stunden Rühren bei 25°C wurde in Wasser eingerührt, mit Essigsäureethylester extrahiert, die organischen Phasen mit IN Salzsäure extrahiert, getrocknet und das Lösungsmittel entfernt. Man erhielt 0.9 g beiger Kristalle.0.8 g (2 mmol) l-chloro-2- (8-chloro-4, 4-dimethyl-l, 1-dioxothio-chroman-7-yl) -carbonyl-cyclohex-l-en-3-one were obtained in 10 ml tetrahydrofuran dissolved, 0.29 g (2 mmol) 4-chlorothiophenol and 0.22 g (2.2 mmol) triethylamine added dropwise. After stirring at 25 ° C. for 2 hours, the mixture was stirred into water, extracted with ethyl acetate, the organic phases were extracted with 1N hydrochloric acid, dried and the solvent was removed. 0.9 g of beige crystals were obtained.
2- (8-Chlor-4 , 4-dimethyl-l, l-dioxothiochroman-7 -yl) -carbonyl-1- (4- chlorphenylsulfonyl) -cyclohex-l-en-3-on (Verbindung 3.4)2- (8-chloro-4, 4-dimethyl-l, l-dioxothiochroman-7 -yl) carbonyl-1- (4-chlorophenylsulfonyl) cyclohex-l-en-3-one (compound 3.4)
0.5 g (0.98 mmol) 2- (8-Chlor-4 , 4-dimethyl-l, 1-dioxothio- chroman-7 -yl) -carbonyl-1- (4-chlorphenylthio) -cyclohex-l-en-3-on wurden in 20 ml Methylenchlorid gelöst und 0.68 g (2.16 mmol)0.5 g (0.98 mmol) 2- (8-chloro-4, 4-dimethyl-l, 1-dioxothio-chroman-7 -yl) -carbonyl-1- (4-chlorophenylthio) -cyclohex-l-en-3- on were dissolved in 20 ml of methylene chloride and 0.68 g (2.16 mmol)
3-Chlorperbenzoesäure (55%-ig) zugegeben. Nach 16 Stunden Rühren bei 25°C wurde mit weiterem Methylenchlorid verdünnt, mit Natriumhydrogensulfit-Lösung und Natriumhydrogencarbonat-Lösung gewaschen, getrocknet und das Lösungsmittel entfernt. Man erhielt 0.5 g cremefarbene Kristalle.3-Chloroperbenzoic acid (55%) added. After stirring at 25 ° C. for 16 hours, the mixture was diluted with further methylene chloride, washed with sodium bisulfite solution and sodium hydrogen carbonate solution, dried and the solvent was removed. 0.5 g of cream-colored crystals were obtained.
2- (8-Chlor-4, 4-dimethyl-l, l-dioxothiochroman-7 -yl) -carbonyl-1- phenylthio-cyclohex-l-en-3-on (Verbindung 3.7)2- (8-chloro-4, 4-dimethyl-l, l-dioxothiochroman-7 -yl) carbonyl-1-phenylthio-cyclohex-l-en-3-one (compound 3.7)
0.7 g (1.75 mmol) l-Chlor-2- (8-chlor-4 , 4-dimethyl-l, 1-dioxothio- chroman-7 -yl) -carbonyl-cyclohex-l-en-3-on wurden in 10 ml Tetra- hydrofuran gelöst, 0.19 g (1.75 mmol) Thiophenol und 0.19 g (1.92 mmol) Triethylamin zugetropft. Nach 2 Stunden Rühren bei 25°C wurde in Wasser eingerührt, mit Essigsäureethylester extrahiert, die organischen Phasen mit IN Salzsäure extrahiert, getrocknet und eingeengt. Man erhielt 0.8 g beiger Kristalle. 50.7 g (1.75 mmol) l-chloro-2- (8-chloro-4, 4-dimethyl-l, 1-dioxothio-chroman-7-yl) -carbonyl-cyclohex-l-en-3-one were obtained in 10 ml tetrahydrofuran dissolved, 0.19 g (1.75 mmol) thiophenol and 0.19 g (1.92 mmol) of triethylamine was added dropwise. After stirring at 25 ° C. for 2 hours, the mixture was stirred into water, extracted with ethyl acetate, the organic phases were extracted with 1N hydrochloric acid, dried and concentrated. 0.8 g of beige crystals were obtained. 5
2- (8-Chlor-4 , 4-dimethyl-l, l-dioxothiochroman-7 -yl) -carbonyl-1- phenylsulfonyl-cyclohex-l-en-3-on (Verbindung 3.5)2- (8-chloro-4, 4-dimethyl-l, l-dioxothiochroman-7 -yl) carbonyl-1-phenylsulfonyl-cyclohex-l-en-3-one (compound 3.5)
0.4 g (0.84 mmol) 2- (8-Chlor-4 , 4-dimethyl-l, 1-dioxothio- 10 chroman-7-yl) -carbonyl-l-phenylthio-cyclohex-l-en-3-on wurden in 20 ml Methylenchlorid gelöst und 0.66 g (2.16 mmol) 3-Chlorper- benzoesäure (55%-ig) zugegeben. Nach 16 Stunden Rühren bei 25°C wurde mit weiterem Methylenchlorid verdünnt, mit Natriumhydrogensulfit-Lösung und Natriumhydrogencarbonat-Lösung gewaschen, ge- 15 trocknet und das Lösungsmittel entfernt. Man erhielt 0.4 g cremefarbene Kristalle.0.4 g (0.84 mmol) of 2- (8-chloro-4, 4-dimethyl-l, 1-dioxothio-10 chroman-7-yl) -carbonyl-l-phenylthio-cyclohex-l-en-3-one were added in 20 ml methylene chloride dissolved and 0.66 g (2.16 mmol) 3-chloroperbenzoic acid (55%) added. After stirring at 25 ° C. for 16 hours, the mixture was diluted with further methylene chloride, washed with sodium hydrogen sulfite solution and sodium hydrogen carbonate solution, dried and the solvent was removed. 0.4 g of cream-colored crystals were obtained.
2- (8-Chlor-4, 4-dimethyl-l, l-dioxothiochroman-7 -yl) -carbonyl-1- ethylthio-cyclohex-l-en-3-on (Verbindung 3.8)2- (8-chloro-4, 4-dimethyl-l, l-dioxothiochroman-7 -yl) carbonyl-1-ethylthio-cyclohex-l-en-3-one (compound 3.8)
2020th
0.7 g (1.75 mmol) l-Chlor-2- (8-chlor-4 , 4-dimethyl-l, 1-dioxothio- chroman-7 -yl) -carbonyl-cyclohex-l-en-3-on wird in 20 ml Tetrahy- drofuran gelöst, 0.11 g (1.75 mmol) Ethanthiol und 0.19 g (1.92 mmol) Triethylamin zugetropft. Nach 2 Stunden Rühren bei 25°C0.7 g (1.75 mmol) l-chloro-2- (8-chloro-4, 4-dimethyl-l, 1-dioxothio-chroman-7 -yl) -carbonyl-cyclohex-l-en-3-one becomes in 20 ml of tetrahydrofuran dissolved, 0.11 g (1.75 mmol) of ethanethiol and 0.19 g (1.92 mmol) of triethylamine added dropwise. After stirring for 2 hours at 25 ° C
25 wurde in Wasser eingerührt, mit Essigsäureethylester extrahiert, die organischen Phasen mit IN Salzsäure extrahiert, getrocknet und das Lösungsmittel entfernt. Man erhielt 0.4 g beiger Kristalle.25 was stirred into water, extracted with ethyl acetate, the organic phases extracted with 1N hydrochloric acid, dried and the solvent removed. 0.4 g of beige crystals were obtained.
30 2- (8-Chlor-4 , 4-dimethyl-l, l-dioxothiochroman-7 -yl) -carbo- nyl-l-ethylsulfonyl-cyclohex-l-en-3-on (Verbindung 3.9)30 2- (8-chloro-4, 4-dimethyl-l, l-dioxothiochroman-7 -yl) -carbonyl-l-ethylsulfonyl-cyclohex-l-en-3-one (compound 3.9)
0.2 g (0.47 mmol) 2- (8-Chlor-4 , 4-dimethyl-l, 1-dioxothio- chroman-7-yl) -carbonyl) -l-ethylthio-cyclohex-l-en-3-on wurden in0.2 g (0.47 mmol) of 2- (8-chloro-4, 4-dimethyl-l, 1-dioxothio-chroman-7-yl) -carbonyl) -l-ethylthio-cyclohex-l-en-3-one were added in
35 20 ml Methylenchlorid gelöst und 0.37 g (1.17 mmol) 3-Chlorper- benzoesäure (55%-ig) zugegeben. Nach 16 Stunden Rühren bei 25°C wurde mit weiterem Methylenchlorid verdünnt, mit Natriumhydrogensulfit-Lösung und Natriumhydrogencarbonat-Lösung gewaschen, getrocknet und das Lösungsmittel entfernt. Man erhielt 0.17 g cre-35 20 ml methylene chloride dissolved and 0.37 g (1.17 mmol) 3-chloroperbenzoic acid (55%) added. After stirring at 25 ° C. for 16 hours, the mixture was diluted with further methylene chloride, washed with sodium bisulfite solution and sodium hydrogen carbonate solution, dried and the solvent was removed. 0.17 g of cre-
40 mefarbene Kristalle.40 sea-colored crystals.
2- (8-Chlor-4 , 4-dimethyl-l, l-dioxothiochroman-7 -yl) -carbonyl-1- (N, O-dimethylhydroxylamino) -cyclohex-l-en-3-on (Verbindung 3.10)2- (8-chloro-4, 4-dimethyl-l, l-dioxothiochroman-7 -yl) carbonyl-1- (N, O-dimethylhydroxylamino) cyclohex-l-en-3-one (compound 3.10)
5 0.5 g (1.25 mmol) l-Chlor-2- (8-chlor-4 , 4-dimethyl-l, 1-dioxothio- chroman-7 -yl) -carbonyl-cyclohex-l-en-3-on wurden in 10 ml Tetra- hydrofuran gelöst, 0.13 g (1.37 mmol) N,0-Dimethylhydroxylaminhy- drochlorid und 0.28 g (2.74 mmol) Triethylamin zugetropft. Nach 25 Stunden Rühren bei 25°C wurde in Wasser eingerührt, mit Essigsäureethylester extrahiert, die organischen Phasen mit IN Salzsäure extrahiert, getrocknet und das Lösungsmittel entfernt. Man 5 erhielt 0.4 g beiger Kristalle.5 0.5 g (1.25 mmol) l-chloro-2- (8-chloro-4, 4-dimethyl-l, 1-dioxothio-chroman-7 -yl) -carbonyl-cyclohex-l-en-3-one were added in 10 ml tetrahydrofuran dissolved, 0.13 g (1.37 mmol) N, 0-dimethylhydroxylamine hy drochloride and 0.28 g (2.74 mmol) of triethylamine were added dropwise. After stirring at 25 ° C. for 25 hours, the mixture was stirred into water, extracted with ethyl acetate, the organic phases were extracted with 1N hydrochloric acid, dried and the solvent was removed. 5 g of 0.4 g of beige crystals were obtained.
1- (Phenylcarbonyloxy) -2- (4, 4 , 8 - trimethyl-1, l-dioxothiochro- man-7 -yl) -carbonyl-cyclohex-l-en-3 -on (Verbindung 3.22)1- (phenylcarbonyloxy) -2- (4, 4, 8 - trimethyl-1, l-dioxothiochro-man-7 -yl) carbonyl-cyclohex-l-en-3 -one (compound 3.22)
10 Stufe a) 3 - (3-Methyl -2 -butenylthio) -2-methyl -benzoesäuremethyl- ester10 stage a) 3 - (3-methyl -2-butenylthio) -2-methyl-benzoic acid methyl ester
Zu 50 g (0.275 mol) 3-Thio-2-methyl -benzoesäuremethylester in 250 ml Aceton wurden 37.9 g (0.27 mol) Kaliumcarbonat und 43.5 g37.9 g (0.27 mol) of potassium carbonate and 43.5 g were added to 50 g (0.275 mol) of methyl 3-thio-2-methylbenzoate in 250 ml of acetone
15 (0.275 mol) 3-Methyl -2 -butenylbromid getropft und zehn Stunden bei Raumtemperatur gerührt. Nach Abdestillieren des Lösungsmittels wurde der Rückstand in Wasser/Essigsäureethylester aufgenommen, die organische Phase getrocknet, abfiltriert und eingeengt. Ausbeute : 67.9 g (98.9%) gelbes Öl.15 (0.275 mol) of 3-methyl -2-butenyl bromide were added dropwise and the mixture was stirred at room temperature for ten hours. After the solvent had been distilled off, the residue was taken up in water / ethyl acetate, the organic phase was dried, filtered off and concentrated. Yield: 67.9 g (98.9%) yellow oil.
20 !H-NMR (CDC13, δ in ppm) : 7.63 (d,lH); 7.41 (d,lH); 7.16 (t.lH);20 ! H NMR (CDC1 3 , δ in ppm): 7.63 (d, 1H); 7.41 (d, lH); 7.16 (t.lH);
5.25 (m,lH); 3.90 (s,3H), 3.49 (d,2H); 2.60 (s,3H); 1.70 (s,3H); 1.56 (s,3H).5.25 (m, lH); 3.90 (s, 3H), 3.49 (d, 2H); 2.60 (s, 3H); 1.70 (s, 3H); 1.56 (s, 3H).
Stufe b) 4, 4 , 8 -Trimethylthiochroman-7-carbonsäuremethylesterStep b) 4, 4, 8 -trimethylthiochroman-7-carboxylic acid methyl ester
2525
67.9 g (0.27 mol) 3- (3 -Methyl -2 -butenylthio) -2 -methylbenzoesäure- methylester wurden in 600 ml Methylenchlorid gelöst, 206,4 g (1,09 mol) Titantetrachlorid in 600 ml Methylenchlorid bei -5 bis 0°C zugetropft und drei Stunden bei 0°C nachgerührt. Anschließend67.9 g (0.27 mol) of methyl 3- (3-methyl-2-butenylthio) -2-methylbenzoate were dissolved in 600 ml of methylene chloride, 206.4 g (1.09 mol) of titanium tetrachloride in 600 ml of methylene chloride at -5 to 0 ° C added dropwise and stirred at 0 ° C for three hours. Subsequently
30 wurde die Mischung in 1.5 kg Eis und 500 ml gesättigte Ammoniumchlorid-Lösung eingerührt, die organische Phase abgetrennt, getrocknet, und das Lösungsmittel entfernt. Man erhielt 62.9 g eines gelben Öls, das direkt weiter eingesetzt wurde. Zur Produkt - Charakterisierung wurde eine Probe an Kieselgel (Eluent: Cyclohe-The mixture was stirred into 1.5 kg of ice and 500 ml of saturated ammonium chloride solution, the organic phase was separated off, dried and the solvent was removed. 62.9 g of a yellow oil were obtained, which was used directly. A sample of silica gel (eluent: cyclohe-
35 xan/Essigsäureethylester = 10/1) chromatographiert . Schmelzpunkt: 63°C35 xan / ethyl acetate = 10/1) chromatographed. Melting point: 63 ° C
Stufe c) 4 , 4, 8 -Trimethylthiochroman-7-carbonsäureStep c) 4, 4, 8 -trimethylthiochroman-7-carboxylic acid
40 62.9 g 4 , 4 , 8 -Trimethylthiochroman-7-carbonsäuremethylester wurden in 600 ml eines 1 : 1 Wasser/Methanol -Gemisches vorgelegt und 15.1 g (0.377 mol) Natriumhydroxid zugegeben. Die Lösung wurde dann drei Stunden zum Rückfluß erhitzt, das organische Lösungsmittel entfernt, 200 ml Wasser zugegeben und unter Kühlung mit40 62.9 g of 4, 4, 8 -trimethylthiochroman-7-carboxylic acid methyl ester were placed in 600 ml of a 1: 1 water / methanol mixture and 15.1 g (0.377 mol) of sodium hydroxide were added. The solution was then refluxed for three hours, the organic solvent was removed, 200 ml of water were added and the mixture was cooled with
45 konz . Salzsäure sauer gestellt. Der ausgefallene Niederschlag wurde abgesaugt, mit Wasser gewaschen und getrocknet. Ausbeute: 57.2 g Schmelzpunkt: 212°C45 conc. Hydrochloric acid acidified. The precipitate was filtered off, washed with water and dried. Yield: 57.2 g Melting point: 212 ° C
Stufe d) 4 , 4 , 8-Trimethyl-l, l-dioxothiochroman-7-carbonsäureStep d) 4, 4, 8-trimethyl-l, l-dioxothiochroman-7-carboxylic acid
5 57.2 g (0.24 mol) 4 , 4 , 8-Trimethylthiochroman-7-carbonsäure wurden in 500 ml Eisessig gelöst und eine Spatelspitze Natriumwolframat zugegeben. Bei 50 bis 60°C wurden 60.4 g (0.53 mol) 30 %iges Wasserstoffperoxid zugetropft, drei Stunden bei 50°C nachgerührt, in Eiswasser eingerührt und die ausgefallenen weißen Nadeln abfil- 10 triert, mit Wasser gewaschen und getrocknet. Ausbeute: 47.2 g (72.7 %) Schmelzpunkt: 280°C (Zersetzung)5 57.2 g (0.24 mol) of 4, 4, 8-trimethylthiochroman-7-carboxylic acid were dissolved in 500 ml of glacial acetic acid and a spatula tip of sodium tungstate was added. 60.4 g (0.53 mol) of 30% hydrogen peroxide were added dropwise at 50 to 60 ° C., the mixture was stirred at 50 ° C. for three hours, stirred into ice water and the precipitated white needles were filtered off, washed with water and dried. Yield: 47.2 g (72.7%) Melting point: 280 ° C (decomposition)
Stufe e) 4 , 4 , 8-Trimethyl-l, l-dioxothiochroman-7-carbonsäure- 15 ChloridStage e) 4, 4, 8-trimethyl-l, l-dioxothiochroman-7-carboxylic acid-15 chloride
20.0 g (0.075 mol) 4 , 4 , 8-Trimethyl-l , l-dioxothiochroman-7-carbon- säure wurden in 200 ml Toluol gelöst, drei Tropfen Dimethylform- amid sowie 10.7 g (0.09 mol) Thionylchlorid zugegeben. Nach drei 20 Stunden Erhitzen unter Rückfluß wurde das Lösungsmittel entfernt und das zurückbleibende farblose Öl (Ausbeute 21.3 g) direkt weiter eingesetzt.20.0 g (0.075 mol) of 4, 4, 8-trimethyl-l, l-dioxothiochroman-7-carboxylic acid were dissolved in 200 ml of toluene, three drops of dimethylformamide and 10.7 g (0.09 mol) of thionyl chloride were added. After three 20 hours of heating under reflux, the solvent was removed and the remaining colorless oil (yield 21.3 g) was used directly.
Stufe f) 2 - (4, 4, 8-Trimethyl-l, l-dioxothiochroman-7-yl) carbo- 25 nyl -1, 3 -cyclohexandionStep f) 2 - (4, 4, 8-trimethyl-l, l-dioxothiochroman-7-yl) carbo- 25 nyl -1, 3 -cyclohexanedione
2.1 g (19 mmol) 1, 3 -Cyclohexandion und 4.9 g (49 mmol) Triethylamin wurden in 50 ml Acetonitril gelöst und 5.0 g (19 mmol) 4,4, 8-Trimethyl-l, l-dioxothiochroman-7-carbonsäurechlorid in2.1 g (19 mmol) 1, 3 -cyclohexanedione and 4.9 g (49 mmol) triethylamine were dissolved in 50 ml acetonitrile and 5.0 g (19 mmol) 4,4, 8-trimethyl-l, l-dioxothiochroman-7-carboxylic acid chloride in
30 50 ml Acetonitril zugetropft. Nach vierzehn Stunden Rühren bei Raumtemperatur wurden 0,05 ml Trimethylsilylcyanid zugetropft, vier Stunden bei Raumtemperatur gerührt, das Lösungsmittel entfernt, der Rückstand in 2 %iger Natriumhydrogencarbonat -Lösung aufgenommen und je einmal mit Essigsäureethylester und Diethyle-30 50 ml of acetonitrile were added dropwise. After fourteen hours of stirring at room temperature, 0.05 ml of trimethylsilyl cyanide was added dropwise, the mixture was stirred at room temperature for four hours, the solvent was removed, the residue was taken up in 2% sodium hydrogen carbonate solution and each time with ethyl acetate and diethyl
35 ther extrahiert. Die Wasserphase wurde mit konz . Salzsäure auf pH 3 gestellt, der Niederschlag abfiltriert, mit Wasser gewaschen und getrocknet .35 ther extracted. The water phase was with conc. Hydrochloric acid adjusted to pH 3, the precipitate filtered off, washed with water and dried.
Ausbeute: 5.1 g (74 %) farblose Kristalle Schmelzpunkt: 165°CYield: 5.1 g (74%) of colorless crystals. Melting point: 165 ° C.
4040
Stufe g) 1- (Phenylcarbonyloxy) -2 - (4 , 4 , 8 - trimethyl-1, 1-dioxo- thiochroman-7 -yl) -carbonyl -cyclohex-1-en- 3 -on (Verbindung 3.22)Step g) 1- (phenylcarbonyloxy) -2 - (4, 4, 8 - trimethyl-1, 1-dioxothiochroman-7 -yl) carbonylcyclohex-1-ene-3 -one (compound 3.22)
5 0.8 g (2.2 mmol) 2 - (4 , 4 , 8 -Trimethyl - 1 , 1 -dioxothiochro- man-7 -yl) -carbonyl - 1, 3 -cyclohexandion wurden in 10 ml Methylenchlorid gelöst, 0.17 g (2.2 mmol) Pyridin und 0.31 g (2.2 mmol) Benzoylchlorid zugegeben. Nach zwei Stunden Rühren bei Raumtemperatur wurde Wasser hinzugefügt, die organische Phase abgetrennt, mit 2 N Salzsäure extrahiert und getrocknet. Anschließend wurde das Lösungsmittel abdestilliert und der Rückstand an Kieselgel chromatographiert .5 0.8 g (2.2 mmol) of 2 - (4, 4, 8 -trimethyl - 1, 1 -dioxothiochro-man-7 -yl) -carbonyl - 1, 3 -cyclohexanedione were dissolved in 10 ml of methylene chloride, 0.17 g (2.2 mmol ) Pyridine and 0.31 g (2.2 mmol) Benzoyl chloride added. After stirring at room temperature for two hours, water was added, the organic phase was separated off, extracted with 2N hydrochloric acid and dried. The solvent was then distilled off and the residue was chromatographed on silica gel.
Ausbeute: 0.35 g (47 %) farblose Kristalle Schmelzpunkt: 189°C (Zersetzung)Yield: 0.35 g (47%) of colorless crystals. Melting point: 189 ° C. (decomposition)
1- Chlor -2- [ (8-methyl-2,3-dihydro-l,l,4,4-tetraoxobenz [l,4]di- thiin-7-yl) -carbonyl] -4,4,6, 6 - tetramethyl - 1 -cyclohexen-3 , 5-dion (Verbindung 4.1)1- chlorine -2- [(8-methyl-2,3-dihydro-l, 1,4,4-tetraoxobenz [1,4, di] thiin-7-yl) carbonyl] -4,4,6, 6-tetramethyl-1-cyclohexene-3, 5-dione (compound 4.1)
Stufe a) 3- (2-Bromethylthio) -2-methyl -benzoesäuremethylesterStep a) 3- (2-bromoethylthio) -2-methylbenzoic acid methyl ester
Zu 40.0 g (0.22 mol) 3-Thio-2-methyl-benzoesäuremethylester in 500 ml Aceton wurden 30.3 g (0.22 mol) Kaliumcarbonat gegeben und 82.6 g (0.22 mol) 1, 2-Dibromethan getropft. Nach zehn Stunden Rühren bei Raumtemperatur wurde das Lösungsmittel abdestilliert, der Rückstand in Wasser/Essigsäureethylester aufgenommen, die or- ganische Phase getrocknet und eingeengt. Das zurückbleibende Öl wurde mit Essigsäureester/Cyclohexan = 1/10 über Kieselgel chromatographiert .30.3 g (0.22 mol) of potassium carbonate were added to 40.0 g (0.22 mol) of methyl 3-thio-2-methylbenzoate in 500 ml of acetone, and 82.6 g (0.22 mol) of 1,2-dibromoethane were added dropwise. After stirring for ten hours at room temperature, the solvent was distilled off, the residue was taken up in water / ethyl acetate, the organic phase was dried and concentrated. The remaining oil was chromatographed on silica gel with acetic acid ester / cyclohexane = 1/10.
Ausbeute : 42.7 g (67.2 %) farblose Kristalle. iH-NMR (CDC13, δ in ppm) : 7.68 (d,lH); 7.51 (d,lH); 7.20 (t,lH); 3.90 (s,3H), 3.41 (m,2H); 3.25 (m,2H);Yield: 42.7 g (67.2%) of colorless crystals. i H NMR (CDC1 3 , δ in ppm): 7.68 (d, lH); 7.51 (d, 1H); 7.20 (t, lH); 3.90 (s, 3H), 3.41 (m, 2H); 3.25 (m, 2H);
2.62 (s,3H) .2.62 (s, 3H).
Stufe b) 3- (2-Methylsulfonylthioethylthio) -2-methyl -benzoesäuremethylesterStep b) 3- (2-methylsulfonylthioethylthio) -2-methylbenzoic acid methyl ester
Zu 42.7 g (0.148 mol) 3- (2-Bromethylthio) -2-methyl -benzoesäuremethylester in 400 ml Ethanol wurden 33.2 g (0.22 mol) Kalium-Methylsulfonylthiolat gegeben und fünf Stunden unter Rückfluß erhitzt. Nach Entfernen des Lösungsmittel wurde der Rückstand in Wasser/Essigsäureethylester aufgenommen, getrocknet und eingeengt. Das zurückbleibende Öl wurde mit Essigsäureethylester/Cy- clohexan = 1/4 an Kieselgel chromatographiert. Ausbeute : 33.2 g (67.2 %) gelbes Öl. Schmelzpunkt: 55°C33.2 g (0.22 mol) of potassium methylsulfonylthiolate were added to 42.7 g (0.148 mol) of methyl 3- (2-bromoethylthio) -2-methylbenzoate in 400 ml of ethanol and the mixture was heated under reflux for five hours. After removal of the solvent, the residue was taken up in water / ethyl acetate, dried and concentrated. The remaining oil was chromatographed on silica gel with ethyl acetate / cyclohexane = 1/4. Yield: 33.2 g (67.2%) yellow oil. Melting point: 55 ° C
Stufe c) 8-Methyl-2 , 3-dihydro-benz [1, 4] dithiin -7-carbonsäure- methylesterStep c) 8-methyl-2, 3-dihydro-benz [1, 4] dithiine -7-carboxylic acid methyl ester
49.2 g (0.154 mol) 3- (2-Methylsulfonylthioethylthio) -2-methyl - benzoesäuremethylester wurden in 500 ml Methylenchlorid gelöst, 80.2 g (0.308 mol) Zinntetrachlorid zugegeben, drei Stunden unter Rückfluß erhitzt und zehn Stunden bei Raumtemperatur nachgerührt. Die Mischung wurde dann mit Wasser und gesättigter Natriumhydro- gencarbonatlösung gewaschen, die organische Phase abgetrennt, getrocknet und eingeengt. Das zurückbleibende Öl wurde mit Essig - säureethylester/Cyclohexan = 1/10 an Kieselgel chromatographiert. Ausbeute : 17.1 g (46.3 %) farblose Kristalle Schmelzpunkt: 57°C49.2 g (0.154 mol) of 3- (2-methylsulfonylthioethylthio) -2-methyl-benzoic acid methyl ester were dissolved in 500 ml of methylene chloride, 80.2 g (0.308 mol) of tin tetrachloride were added, the mixture was refluxed for three hours and stirred at room temperature for ten hours. The mixture was then washed with water and saturated sodium hydrogen carbonate solution, the organic phase was separated off, dried and concentrated. The remaining oil was chromatographed on silica gel with ethyl acetate / cyclohexane = 1/10. Yield: 17.1 g (46.3%) colorless crystals. Melting point: 57 ° C
Stufe d) 8-Methyl-2, 3-dihydro-benz [1, 4] dithiin -7-carbonsäureStep d) 8-methyl-2, 3-dihydro-benz [1, 4] dithiine -7-carboxylic acid
9.6 g (0.04 mol) 8-Methyl-2 , 3-dihydro-benz [1, 4] dithiin-7-carbon- säuremethylester wurden in 100 ml eines 1 : 1 Gemisches aus Wasser/Methanol vorgelegt und 2.4 g (0.06 mol) Natriumhydroxid zugegeben. Die Lösung wurde zwei Stunden unter Rückfluß erhitzt, dann das organische Lösungsmittel abdestilliert, 200 ml Wasser zugege- ben und unter Kühlung mit konz. Salzsäure sauer gestellt. Der ausgefallene Niederschlag wird abgesaugt, mit Wasser gewaschen und getrocknet.9.6 g (0.04 mol) of 8-methyl-2,3-dihydro-benz [1,4] dithiine-7-carboxylic acid methyl ester were placed in 100 ml of a 1: 1 mixture of water / methanol and 2.4 g (0.06 mol) Sodium hydroxide added. The solution was heated under reflux for two hours, then the organic solvent was distilled off, 200 ml of water were added and the mixture was cooled with conc. Hydrochloric acid acidified. The precipitate is filtered off, washed with water and dried.
Ausbeute: 8.1 g (89,6 %) farblose Kristalle Schmelzpunkt: 175°CYield: 8.1 g (89.6%) colorless crystals. Melting point: 175 ° C
Stufe e) 8-Methyl-2, 3-dihydro-l,l, 4, 4-tetraoxobenz [1,4] dithiin- 7-carbonsäureStep e) 8-methyl-2, 3-dihydro-l, 1,4, 4-tetraoxobenz [1,4] dithiine-7-carboxylic acid
19.4 g (0.086 mol) 8-Methyl-2 , 3-dihydro-benz [1, 4] dithiin- 7-carbonsäure wurden in 200 ml Essigsäure gelöst und eine Spatel - spitze Natriumwolframat zugegeben. Bei 50 - 60°C wurden dann hierzu 42.8 g (0.38 mol) 30 %iges Wasserstoffperoxid getropft.19.4 g (0.086 mol) of 8-methyl-2, 3-dihydro-benz [1, 4] dithiine-7-carboxylic acid were dissolved in 200 ml of acetic acid and a spatula-pointed sodium tungstate was added. 42.8 g (0.38 mol) of 30% hydrogen peroxide were then added dropwise at 50-60 ° C.
Nach fünf Stunden Rühren bei 50°C wurde abgekühlt, in Eiswasser eingerührt und die ausgefallenen weißen Nadeln abfiltriert, mit Wasser gewaschen und getrocknet.After stirring at 50 ° C. for five hours, the mixture was cooled, stirred into ice water and the precipitated white needles were filtered off, washed with water and dried.
Ausbeute: 21.7 g (87.2 %)Yield: 21.7 g (87.2%)
Schmelzpunkt: 282°CMelting point: 282 ° C
Stufe f) 8-Methyl-2,3-dihydro-l, 1, 4, 4-tetraoxobenz [1,4] dithiin- 7-carbonsäurechloridStep f) 8-methyl-2,3-dihydro-l, 1,4,4-tetraoxobenz [1,4] dithiine-7-carboxylic acid chloride
10.0 g (0.0345 mol) 8-Methyl-2 , 3-dihydro-l , 1, 4 , 4-tetraoxo- benz [1, 4] dithiin-7-carbonsäure wurden in 100 ml Toluol gelöst, zwei Tropfen Dimethylformamid und anschließend 4.5 g (0.038 mol) Thionylchlorid zugegeben. Nach vier Stunden Rühren unter Rückfluß wurde eingeengt. Das zurückbleibende farblose Öl (Ausbeute 10.6 g) konnte direkt weiter eingesetzt werden. Stufe g) 2- (8-Methyl-2 , 3-dihydro-l, 1, 4 , 4-tetraoxobenz [l,4]di- thiin-7-yl) -carbonyl -4, 4,6,6 -tetramethyl -5 -oxo-1, 3 -cyclohexandion10.0 g (0.0345 mol) of 8-methyl-2, 3-dihydro-l, 1, 4, 4-tetraoxobenzene [1, 4] dithiine-7-carboxylic acid were dissolved in 100 ml of toluene, two drops of dimethylformamide and then 4.5 g (0.038 mol) of thionyl chloride were added. After stirring under reflux for four hours, the mixture was concentrated. The remaining colorless oil (yield 10.6 g) could be used directly. Step g) 2- (8-methyl-2, 3-dihydro-l, 1, 4, 4-tetraoxobenz [1,4, di] thiin-7-yl) carbonyl -4, 4,6,6 -tetramethyl -5-oxo-1,3-cyclohexanedione
2.95 g (16.2 mmol) 4 , 4 , 6 , 6 -Tetramethyl -5 -oxo- 1 , 3 -cyclohexandion und 4.9 g (4.9 mmol) Triethylamin wurden in 50 ml Acetonitril gelöst und 5.0 g (16.2 mmol) 8-Methyl-2 , 3 -dihydro-1, 1, 4, 4 - tetra- oxobenz [1, 4] dithiin-7 -carbonsäurechlorid in 50 ml Acetonitril zugetropft. Nach vierzehn Stunden Rühren bei Raumtemperatur wurden 0,05 ml Trimethylsilylcyanid zugetropft, vier Stunden bei Raumtemperatur gerührt, das Lösungsmittel entfernt, der Rückstand in 2 %iger Natriumhydrogencarbonat -Lösung aufgenommen und je einmal mit Essigsäureethylester und Diethylether extrahiert. Die Wasserphase wurde mit konz . Salzsäure auf pH 3 gestellt, der Nieder- schlag abfiltriert, mit Wasser gewaschen und getrocknet. Ausbeute: 4.8 g (65 %) farblose Kristalle Schmelzpunkt: 146°C (Zersetzung)2.95 g (16.2 mmol) 4, 4, 6, 6 -tetramethyl -5-oxo- 1, 3 -cyclohexanedione and 4.9 g (4.9 mmol) triethylamine were dissolved in 50 ml acetonitrile and 5.0 g (16.2 mmol) 8-methyl- 2, 3 -dihydro-1, 1, 4, 4 - tetra-oxobenz [1, 4] dithiine-7-carboxylic acid chloride in 50 ml of acetonitrile was added dropwise. After fourteen hours of stirring at room temperature, 0.05 ml of trimethylsilyl cyanide was added dropwise, the mixture was stirred for four hours at room temperature, the solvent was removed, the residue was taken up in 2% sodium hydrogen carbonate solution and extracted once each with ethyl acetate and diethyl ether. The water phase was with conc. Hydrochloric acid adjusted to pH 3, the precipitate filtered off, washed with water and dried. Yield: 4.8 g (65%) colorless crystals Melting point: 146 ° C (decomposition)
Stufe h) l-Chlor-2- (8-methyl-2 , 3-dihydro-l, 1, 4 , 4-tetra- oxobenz [1,4] dithiin- 7 -yl) -carbonyl -4, 4,6, 6- tetramethyl- l-cyclohexen-3 , 5 -dion (Verbindung 4.1)Step h) 1-chloro-2- (8-methyl-2,3-dihydro-1,1,4,4-tetraoxobenz [1,4] dithiine-7-yl) carbonyl -4,4,6 , 6-tetramethyl-l-cyclohexene-3, 5-dione (compound 4.1)
0.5 g (1.1 mmol) 2 - (8-Methyl-2 , 3-dihydro-l, 1, 4 , 4-tetraoxo- benz [1,4] dithiin-7 -yl) -carbonyl -4, 4 , 6, 6- tetramethyl -1, 3, 5-cyclo- hexantrion wurden in 10 ml Methylenchlorid gelöst, 0.28 g0.5 g (1.1 mmol) 2 - (8-methyl-2, 3-dihydro-l, 1, 4, 4-tetraoxobenzene [1,4] dithiin-7-yl) -carbonyl -4, 4, 6, 6- tetramethyl -1, 3, 5-cyclohexantrione were dissolved in 10 ml methylene chloride, 0.28 g
(2.2 mmol) Oxalylchlorid und 2 Tropfen Dimethylformamid zugegeben. Nach einer Stunde Rühren bei 25°C wurde das Lösungsmittel ent ernt. Ausbeute: 0.3 g (58 %) farblose Kristalle (2.2 mmol) oxalyl chloride and 2 drops of dimethylformamide were added. After stirring for one hour at 25 ° C, the solvent was removed. Yield: 0.3 g (58%) colorless crystals
Tabelle 3Table 3
oO
IIII
Ό c siSi c si
O σ>O σ>
II XII X
1 co1 co
Die Verbindungen der Formel I und deren landwirtschaftlich brauchbaren Salze eignen sich sowohl als Isomerengemische als auch in Form der reinen Isomeren - als Herbizide. Die herbiziden Mittel, die Verbindungen der Formel I enthalten, bekämpfen Pflanzenwuchs auf Nichtkulturflächen sehr gut, besonders bei hohen Aufwandmengen. In Kulturen wie Weizen, Reis, Mais, Soja und Baumwolle wirken sie gegen Unkräuter und Schadgräser, ohne die Kulturpflanzen nennenswert zu schädigen. Dieser Effekt tritt vor al- lern bei niedrigen Aufwandmengen auf. The compounds of formula I and their agriculturally useful salts are suitable both as isomer mixtures and in the form of the pure isomers - as herbicides. The herbicidal compositions which contain compounds of the formula I control vegetation very well on non-cultivated areas, especially when high amounts are applied. In crops such as wheat, rice, corn, soybeans and cotton, they act against weeds and grass weeds without significantly damaging the crop plants. This effect occurs above all at low application rates.
In Abhängigkeit von der jeweiligen Applikationsmethode können die Verbindungen der Formel I bzw. sie enthaltenden herbiziden Mittel noch in einer weiteren Zahl von Kulturpflanzen zur Beseitigung unerwünschter Pflanzen eingesetzt werden. In Betracht kommen beispielsweise folgende Kulturen:Depending on the particular application method, the compounds of the formula I or herbicidal compositions comprising them can also be used in a further number of crop plants for eliminating undesired plants. The following crops are considered, for example:
Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica) , Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum,Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea libericaus), Cucumodison , Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum,
(Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium) , Helianthus annuus, Hevea brasiliensis, Hordeum vulgäre, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec, Manihot esculenta, Medicago sativa, Musa spec, Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Seeale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgäre), Theobroma cacao, Trifo- lium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera und Zea mays .(Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgäre, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersica, Musus spec, manus spec, Medicinal specimen, Malus spec. Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarle, Seeale Solanum tuberosum, sorghum bicolor (see vulgar), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.
Darüber hinaus können die Verbindungen der Formel I auch in Kul- turen, die durch Züchtung einschließlich gentechnischer Methoden gegen die Wirkung von Herbiziden tolerant sind, verwandt werden.In addition, the compounds of the formula I can also be used in crops which are tolerant to the action of herbicides by breeding, including genetic engineering methods.
Die Verbindungen der Formel 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, Öldispersionen, 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 of the formula I or the herbicidal compositions comprising them can be used, for example, in the form of directly sprayable aqueous solutions, powders, suspensions, including high-strength aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, Scattering agents or granules can be applied by spraying, atomizing, 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.
Die herbiziden Mittel enthalten eine herbizid wirksame Menge mindestens einer Verbindung der Formel I oder eines landwirtschaftlich brauchbaren Salzes von I und für die Formulierung von Pflan- zenschutzmitteln übliche Hilfsmittel.The herbicidal compositions comprise a herbicidally effective amount of at least one compound of the formula I or an agriculturally useful salt of I and auxiliaries customary for the formulation of crop protection agents.
Als inerte Hilfsstoffe kommen im Wesentlichen in Betracht:The following are essentially considered as inert auxiliaries:
Mineralölfraktionen von mittlerem bis hohem Siedepunkt wie Kerosin und Dieselöl, ferner Kohlenteerole sowie Öle pflanzlichen oder tierischen Ursprungs, aliphatische, cyclische und aromatische Kohlenwasserstoffe, z.B. Paraffin, Tetrahydronaphthalin, alkylierte Naphthaline und deren Derivate, alkylierte Benzole oder deren Derivate, Alkohole wie Methanol, Ethanol, Propanol, Butanol und Cyclohexanol, Ketone wie Cyclohexanon, stark polare Lösungsmittel, z.B. Amine wie N-Methylpyrrolidon und Wasser.Mineral oil fractions of medium to high boiling point such as kerosene and diesel oil, also coal tarols and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Paraffin, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes or their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, strongly polar solvents, e.g. Amines such as N-methylpyrrolidone and water.
Wäßrige Anwendungsformen können aus Emulsionskonzentraten, Suspensionen, Pasten, netzbaren Pulvern oder wasserdispergierbaren Granulaten durch Zusatz von Wasser bereitet werden. Zur Herstellung von Emulsionen, Pasten oder Öldispersionen können die Cyclohexenondioxothiochromanoyl-Derivate der Formel I 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-,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 oil dispersions, the cyclohexenone dioxothiochromanoyl derivatives of the formula I, 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 can also consist of active substance, wetting, adhesive,
Dispergier- oder Emulgiermittel und eventuell Lösungsmittel oder Öl bestehende Konzentrate hergestellt werden, die zur Verdünnung mit Wasser geeignet sind.Dispersants or emulsifiers and possibly solvents or oil existing concentrates are prepared which are suitable for dilution with water.
Als oberflächenaktive Stoffe (Adjuvantien) 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, Poly- oxyethylenoctylphenolether, ethoxyliertes Isooctyl-, Octyl- oder Nonylphenol, Alkylphenyl- , Tributylphenylpolyglykolether, Alkyl - arylpolyetheralkohole, Isocridecylalkohol , Fettalkoholethylen- oxid-Kondensate, ethoxyliertes Rizinusöl, Polyoxyethylen- oder Polyoxypropylenalkylether, Laurylalkoholpolyglykoletheracetat, Sorbitester, Lignin-Sulfitablaugen oder Methylcellulose in Betracht.The surface-active substances (adjuvants) are the alkali, alkaline earth, 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 sulfated hexa-, hepta- and octadecanols as well as fatty alcohol glycol ether, 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, phenyl or nonyl phenyl Tributylphenyl polyglycol ether, alkyl aryl polyether alcohols, isocridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene or Polyoxypropylene alkyl ether, lauryl alcohol polyglycol ether acetate, sorbitol ester, lignin sulfite waste 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 Kieselsäuren, Kieselgele, Silikate, Talkum, Kaolin, Kalkstein, Kalk, Kreide, Bolus, Löß, Ton, Dolomit, Diatomeenerde, Calcium- und Magnesiumsulfat, Magnesiumoxid, gemahlene Kunststoffe, Dünge- mittel, wie Ammoniumsulfat, Ammoniumphosphat, Ammoniumnitrat, Harnstoffe und pflanzliche Produkte wie Getreidemehl, Baumrinden-, Holz- und Nußschalenmehl, Cellulosepulver oder andere feste Trägerstoffe.Granules, e.g. Coated, impregnated and homogeneous granules can be produced by binding the active ingredients to solid carriers. Solid carriers are mineral soils such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, Ammonium nitrate, ureas and vegetable products such as corn flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
Die Konzentrationen der Verbindungen der Formel I in den anwendungsfertigen Zubereitungen können in weiten Bereichen variiert werden. Im allgemeinen enthalten die Formulierungen etwa von 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- Spektrum) eingesetzt.The concentrations of the compounds of the formula I in the ready-to-use preparations can be varied within a wide range. In general, the formulations contain from about 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 folgenden Formulierungsbeispiele verdeutlichen die Herstellung solcher Zubereitungen:The following formulation examples illustrate the preparation of such preparations:
I. 20 Gewichtsteile der Verbindung Nr. 3.1 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 Rizinusöl besteht. Durch Ausgießen und feines Verteilen der Lösung in 100000 Gewichtsteilen Wasser erhält man eine wäßrige Dispersion, die 0,02 Gew.-% des Wirkstoffs enthält.I. 20 parts by weight of compound no. 3.1 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 moles of ethylene oxide and 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight of calcium salt of dodecylbenzenesulfonic acid and 5 parts by weight of Addition product of 40 moles of ethylene oxide with 1 mole of castor oil. By pouring the solution into 100,000 parts by weight of water and finely distributing it therein, an aqueous dispersion is obtained which contains 0.02% by weight of the active ingredient.
II. 20 Gewichtsteile der Verbindung Nr. 3.2 werden in einer Mischung gelöst, die aus 40 Gewichtsteilen Cyclohexanon,II. 20 parts by weight of compound no. 3.2 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 Isooctyl- phenol und 10 Gewichtsteilen des Anlagerungsproduktes von 40 Mol Ethylenoxid an 1 Mol Rizinusöl besteht. Durch Ein- gießen und feines Verteilen der Lösung in 100000 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 moles of ethylene oxide and 1 mole of isooctylphenol and 10 parts by weight of the additive of 40 moles of ethylene oxide in 1 mole of castor oil. Through a- pouring and finely distributing the solution in 100,000 parts by weight of water gives an aqueous dispersion which contains 0.02% by weight of the active ingredient.
III. 20 Gewichtsteile der Verbindung Nr. 3.4 werden in einer Mischung gelöst, die aus 25 Gewichtsteilen Cyclohexanon, 65 Gewichtsteilen einer Mineralölfraktion vom Siedepunkt 210 bis 280°C und 10 Gewichtsteilen des Anlagerungs- produktes von 40 Mol Ethylenoxid an 1 Mol Ricinusöl be- steht. Durch Eingießen und feines Verteilen der Lösung in 100000 Gewichtsteilen Wasser erhält man eine wäßrige Dispersion, die 0,02 Gew.-% des Wirkstoffs enthält.III. 20 parts by weight of compound no. 3.4 are dissolved in a mixture consisting of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction with a boiling point of 210 to 280 ° C. and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. 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.
IV. 20 Gewichtsteile der Verbindung Nr. 3.8 werden mit 3 Gewichtsteilen des Natriumsalzes der Diisobutylnaphthalin- sulfonsäure, 17 Gewichtsteilen des Natriumsalzes einer Ligninsulfonsäure aus einer Sulfit-Ablauge und 60 Gewichtsteilen pulverförmigem Kieselsäuregel gut vermischt und in einer Hammermühle vermählen. Durch feines Verteilen der Mischung in 20000 Gewichtsteilen Wasser erhält man eine Spritzbrühe, die 0,1 Gew.-% des Wirkstoffs enthält.IV. 20 parts by weight of compound no. 3.8 are mixed well with 3 parts by weight of the sodium salt of diisobutylnaphthalenesulfonic acid, 17 parts by weight of the sodium salt of lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel and ground in a hammer mill. By finely distributing the mixture in 20,000 parts by weight of water, a spray liquor is obtained which contains 0.1% by weight of the active ingredient.
V. 3 Gewichtsteile der Verbindung Nr. 3.9 werden mitV. 3 parts by weight of compound no. 3.9 are with
97 Gewichtsteilen feinteiligem Kaolin vermischt. Man erhält auf diese Weise ein Stäubemittel, das 3 Gew.-% des Wirkstoffs 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 der Verbindung Nr. 3.18 werden mitVI. 20 parts by weight of compound no. 3.18 are with
2 Gewichtsteilen Calciumsalz der Dodecylbenzolsulfonsäure, 8 Gewichtsteilen Fettalkoholpolyglykolether, 2 Gewichtsteilen 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 Nr. 3.23 wird in einer Mischung gelöst, die aus 70 Gewichtsteilen Cyclohexanon, 20 Gewichtsteilen ethoxyliertem Isooctylphenol undVII. 1 part by weight of compound no. 3.23 is dissolved in a mixture consisting of 70 parts by weight of cyclohexanone, 20 parts by weight of ethoxylated isooctylphenol and
10 Gewichtsteilen ethoxyliertem Rizinusöl besteht. Man er- hält ein stabiles Emulsionskonzentrat.There are 10 parts by weight of ethoxylated castor oil. A stable emulsion concentrate is obtained.
VIII. 1 Gewichtsteil der Verbindung Nr. 4.1 wird in einer Mischung gelöst, die aus 80 Gewichtsteilen Cyclohexanon und 20 Gewichtsteilen WettolR EM 31 (- nichtionischer Emulgator auf der Basis von ethoxyliertem Rizinusöl) besteht. Man erhält ein stabiles Emulsionskonzentrat. Die Applikation der Verbindungen der Formel I bzw. der herbiziden Mittel kann im Vorauflauf- oder im Nachauflaufverfahren 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) .VIII. 1 part by weight of compound no. 4.1 is dissolved in a mixture consisting of 80 parts by weight of cyclohexanone and 20 parts by weight of Wettol R EM 31 (nonionic emulsifier based on ethoxylated castor oil). A stable emulsion concentrate is obtained. The compounds of the formula I or the herbicidal compositions can be applied pre- or 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 Aufwandmengen an Verbindung der Formel I 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.).The application rates of the compound of the formula I are, depending on the control target, the season, the target plants and the growth stage, 0.001 to 3.0, preferably 0.01 to 1.0 kg / ha of active substance (a.S.).
Zur Verbreiterung des WirkungsSpektrums und zur Erzielung synergistischer Effekte können die Cyclohexenondioxothiochromanoyl-De- rivate der Formel I mit zahlreichen Vertretern anderer herbizider oder wachstumsregulierender Wirkstoffgruppen gemischt und gemeinsam ausgebracht werden. Beispielsweise kommen als Mischungspartner 1, 2 , 4-Thiadiazole, 1, 3 , 4-Thiadiazole, Amide, Aminophosphor- säure und deren Derivate, Aminotriazole, Anilide, Aryloxy-/Hete- roaryloxyalkansäuren und deren Derivate, Benzoesaure und deren Derivate, Benzothiadiazinone, 2-Aroyl-l, 3-cyclohexandione, Hete- roaryl-Aryl-Ketone, Benzylisoxazolidinone, meta-CF3-Phenyl- derivate, Carbamate, Chinolincarbonsäure und deren Derivate, Chloracetanilide, Cyclohexenonoximetherderivate, Diazine, Dichlorpropionsäure und deren Derivate, Dihydrobenzofurane, Dihydrofuran-3-one, Dinitroaniline, Dinitrophenole, Diphenyl- ether, Dipyridyle, Halogencarbonsäuren und deren Derivate, Harnstoffe, 3-Phenyluracile, Imidazole, Imidazolinone, N-Phe- nyl-3, 4, 5, 6-tetrahydrophthalimide, Oxadiazole, Oxirane, Phenole, Aryloxy- und Heteroaryloxyphenoxypropionsäureester, Phenylessig- säure und deren Derivate, 2-Phenylpropionsäure und derenIn order to broaden the spectrum of activity and to achieve synergistic effects, the cyclohexenone dioxothiochromanoyl derivatives of the formula I can be mixed with numerous representatives of other herbicidal or growth-regulating active compound groups and applied together. For example, 1, 2, 4-thiadiazoles, 1, 3, 4-thiadiazoles, amides, aminophosphoric acid and their derivatives, aminotriazoles, anilides, aryloxy- / heteroaryloxyalkanoic acids and their derivatives, benzoic acid and their derivatives, benzothiadiazinones, 2-aroyl-l, 3-cyclohexanediones, heteroaryl aryl ketones, benzylisoxazolidinones, meta-CF 3 phenyl derivatives, carbamates, quinolinecarboxylic acids and their derivatives, chloroacetanilides, cyclohexenone oxime ether derivatives, diazines, dichloropropane hydrofluoric acid and their derivatives -3-one, dinitroaniline, dinitrophenols, diphenyl ether, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3, 4, 5, 6-tetrahydrophthalimides, oxadiazoles, oxiranes, Phenols, aryloxy- and heteroaryloxyphenoxypropionic acid esters, phenylacetic acid and its derivatives, 2-phenylpropionic acid and their
Derivate, Pyrazole, Phenylpyrazole, Pyridazine, Pyridincarbon- säure und deren Derivate, Pyrimidylether, Sulfonamide, Sulfonyl - harnstoffe, Triazine, Triazinone, Triazolinone, Triazolcarboxa- mide und Uracile in Betracht.Derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and their derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides and uracils.
Außerdem kann es von Nutzen sein, die Verbindungen der Formel 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 of the formula 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. It can non-phytotoxic oils and oil concentrates can also be added.
AnwendungsbeispieleExamples of use
Die herbizide Wirkung der Cyclohexenondioxothiochromanoyl-Deri - vate der Formel I ließ sich durch die folgenden Gewächshaus - versuche zeigen:The herbicidal activity of the cyclohexenone dioxothiochromanoyl derivatives of the formula I was demonstrated by the following greenhouse tests:
Als Kulturgefäße dienten Plastikblumentöpfe mit lehmigem Sand mit etwa 3,0 % Humus als Substrat. Die Samen der Testpflanzen wurden nach Arten getrennt eingesät.Plastic flower pots with loamy sand with about 3.0% humus as substrate served as culture vessels. The seeds of the test plants were sown separately according to species.
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 erst dann mit den in Wasser suspendierten oder emul- gierten 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. (aktive Substanz).For the purpose of post-emergence treatment, the test plants, depending on the growth habit, were first grown to a height of 3 to 15 cm and only 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. (active substance).
Die Pflanzen wurden artenspezifisch bei Temperaturen von 10 bis 25°C bzw. 20 bis 35°C gehalten. Die Versuchsperiode erstreckte sich über 2 bis 4 Wochen. Während dieser Zeit wurden die Pflanzen gepflegt, und ihre Reaktion auf die einzelnen Behandlungen wurde ausgewertet.The plants were kept in a species-specific manner at temperatures of 10 to 25 ° C and 20 to 35 ° C. The trial period lasted 2 to 4 weeks. During this time, the plants were cared for and their response to each treatment was evaluated.
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:
Bei Aufwandmengen von 0.5 bzw. 0.25 kg/ha zeigten die Verbindungen 3.2 und 4.1 im Nachauflauf eine sehr gute Wirkung gegen die oben genannten Schadpflanzen. At application rates of 0.5 and 0.25 kg / ha, the compounds 3.2 and 4.1 showed a very good effect against the above-mentioned harmful plants in the post-emergence.

Claims

Patentansprüche claims
1. Cyclohexenondioxothiochromanoyl-Derivate der Formel I1. Cyclohexenone dioxothiochromanoyl derivatives of the formula I.
in der die Variablen folgende Bedeutungen haben:in which the variables have the following meanings:
X Sauerstoff, Schwefel, S=0, S(=0)2, CR4R5, C=0 oder C=NR6;X is oxygen, sulfur, S = 0, S (= 0) 2 , CR 4 R 5 , C = 0 or C = NR 6 ;
R1 Wasserstoff, Nitro, Halogen, Cyano, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, Ci-Cg-Alkoxy, Ci-Cg-Halogenalkoxy, Ci-Cg-Alkylthio, Ci-Cg-Halogenalkylthio, Ci-Cg-Alkylsulfinyl, Ci-Cg-Halogenalkylsulfinyl ,R 1 is hydrogen, nitro, halogen, cyano, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, Ci-Cg-alkylthio, Ci-Cg-haloalkylthio, Ci-Cg- Alkylsulfinyl, Ci-Cg-haloalkylsulfinyl,
Ci-Cg-Alkylsulfonyl , Ci-Cg-Halogenalkylsulfonyl , Aminosulfonyl, N- (Ci-Cg-Alkyl) -aminosulfonyl, N,N-Di- (Ci-Cg-alkyl) -aminosulfonyl, N- (Ci-Cg-Alkyl - sulfonyl) -amino, N- (Ci-Cg-Halogenalkylsulfonyl) - amino, N- (Ci-Cg-Alkyl) -N- (Ci-Cg-alkylsulfonyl) - amino oder N- (Ci-Cg-Alkyl) -N- (Ci-Cg-Halogenalkylsulfonyl) -amino;Ci-Cg-alkylsulfonyl, Ci-Cg-haloalkylsulfonyl, aminosulfonyl, N- (Ci-Cg-alkyl) -aminosulfonyl, N, N-Di- (Ci-Cg-alkyl) -aminosulfonyl, N- (Ci-Cg-alkyl - sulfonyl) amino, N- (Ci-Cg-haloalkylsulfonyl) - amino, N- (Ci-Cg-alkyl) -N- (Ci-Cg-alkylsulfonyl) - amino or N- (Ci-Cg-alkyl) - N- (Ci-Cg-haloalkylsulfonyl) amino;
R2 Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, Ci-Cg-Alkoxy oder Ci-Cg-Halogenalkoxy;R 2 Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkoxy or Ci-Cg-haloalkoxy;
R3 Wasserstoff, Ci-Cg-Alkyl oder Halogen;R 3 is hydrogen, Ci-Cg-alkyl or halogen;
R4,R5 Wasserstoff, Nitro, Halogen, Cyano, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, Ci-Cg-Alkoxy, Ci-Cg-Halogenalkoxy, Ci-Cg-Alkylthio, Ci-Cg-Halogenalkylthio, Ci-Cg-Alkylsulfinyl, Ci-Cg-Halogenalkylsulfinyl , Ci-Cg-Alkylsulfonyl , Ci-Cg-Halogenalkylsulfonyl , N-Ci -Cg -Alkylamino, N-Ci -Cg -Halogenalkylamino, N, N-Di- (Ci-Cg-alkyl) -amino, N-Ci-Cg-Alkoxyamino,R 4 , R 5 are hydrogen, nitro, halogen, cyano, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, Ci-Cg-alkylthio, Ci-Cg-haloalkylthio, Ci -Cg-alkylsulfinyl, Ci-Cg-haloalkylsulfinyl, Ci-Cg-alkylsulfonyl, Ci-Cg-haloalkylsulfonyl, N-Ci -Cg -alkylamino, N-Ci -Cg -haloalkylamino, N, N-di- (Ci-Cg- alkyl) amino, N-Ci-Cg-alkoxyamino,
N- (Ci-Cg -Alkoxy) -N- (Ci-Cg- alkyl) amino, 1-Tetrahy- dropyrrolyl, 1-Piperidinyl, 4 -Morpholinyl oder 1 -Hexahydropyrazinyl ;N- (Ci-Cg-alkoxy) -N- (Ci-Cg-alkyl) amino, 1-tetrahydropyrrolyl, 1-piperidinyl, 4-morpholinyl or 1-hexahydropyrazinyl;
oder R4 und R5 bilden gemeinsam eine -0- (CH2)m-0- , -0- (CH2)m-S- , -S-(CH2)m-S- oder -0- (CH ) n-Kette, die durch einen bis drei Reste aus folgender Gruppe substituiert sein kann: Halogen, Cyano, C1-C4 -Alkyl, C1-C4 -Halogenalkyl oder C1-C4 -Alkoxycarbonyl;or R 4 and R 5 together form a -0- (CH 2 ) m -0-, -0- (CH 2 ) m -S-, -S- (CH 2 ) m -S- or -0- (CH) n chain, which can be substituted by one to three radicals from the following group: halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 alkoxycarbonyl;
oderor
R4 und R5 bilden gemeinsam eine - (CH ) p-Kette, die durchR 4 and R 5 together form a - (CH) p chain through
Sauerstoff oder Schwefel unterbrochen sein kann und/oder durch einen bis vier Reste aus folgender Gruppe substituiert sein kann: Halogen, Cyano, C -C4-Alkyl, C -C4 -Halogenalkyl oder Ci -C4 -Alkoxycarbonyl ;Oxygen or sulfur may be interrupted and / or may be substituted by one to four radicals from the following group: halogen, cyano, C -C 4 alkyl, C -C 4 haloalkyl or Ci -C 4 alkoxycarbonyl;
oderor
R4 und R5 bilden gemeinsam eine Methylidengruppe, die durch einen bis zwei Reste aus folgender Gruppe substituiert sein kann:R 4 and R 5 together form a methylidene group, which can be substituted by one or two radicals from the following group:
Halogen, Cyano, Hydroxy, Formyl, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, Ci-Cg-Alkoxy, Ci-Cg-Halogenalkoxy, Ci-Cg-Alkylthio, Ci-Cg-Halogenalkylthio, Ci-Cg-Alkylsulfinyl, Ci-Cg-Halogenalkylsulfinyl ,Halogen, cyano, hydroxy, formyl, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, Ci-Cg-alkylthio, Ci-Cg-haloalkylthio, Ci-Cg-alkylsulfinyl, Ci-Cg-haloalkylsulfinyl,
Ci-Cg-Alkylsulfonyl oder Ci-Cg-Halogenalkylsulfonyl;Ci-Cg-alkylsulfonyl or Ci-Cg-haloalkylsulfonyl;
R6 Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, Ci-Cg-Alkoxy oder Ci-Cg-Halogenalkoxy;R 6 Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkoxy or Ci-Cg-haloalkoxy;
1 0 bis 4;1 0 to 4;
m 2 bis 4;m 2 to 4;
n 1 bis 5;n 1 to 5;
p 2 bis 5;p 2 to 5;
R7 eine Verbindung Ha oder IlbR 7 is a compound Ha or Ilb
wobei in which
R8 Halogen, OR10, SR10, SOR11, S02R1:L, OS02Rι:L, P0R1;R12,R8 halogen, OR 10 , SR 10 , SOR 11 , S0 2 R 1: L , OS0 2 R ι: L , P0R 1; R 12 ,
OPOR1:LR12, OPSR1:LR12, NR13R14, ONR14R14, N-gebundenes Heterocyclyl oder 0- (N-gebundenes Heterocyclyl) , wobei der Heterocyclyl-Rest der beiden letztgenannten Substituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, Cι-C4-Alkyl, C1-C -Halogenalkyl ,OPOR 1: L R 12 , OPSR 1: L R 12 , NR 13 R 14 , ONR 14 R 14 , N-linked heterocyclyl or 0- (N-linked heterocyclyl), the heterocyclyl radical of the latter two substituents being partial or complete can be halogenated and / or can carry one to three of the following radicals: nitro, cyano, C 1 -C 4 alkyl, C 1 -C haloalkyl,
Cι-C4-Alkoxy oder C1-C4 -Halogenalkoxy;Cι-C 4 -alkoxy or C 1 -C 4 -haloalkoxy;
R9 Nitro, Halogen, Cyano, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, Di- (Ci-Cg-alkoxy) -methyl, Di- (C -Cg-alkyl- thio) -methyl, (Ci-Cg-Alkoxy) (Ci-Cg-alkylthio) - methyl, Hydroxy, Ci-Cg-Alkoxy, Ci-Cg-Halogenalkoxy, Ci-Cg-Alkylthio, Ci-Cg-Halogenalkylthio, C -C6- Alkylsulfinyl, Ci-Cg-Halogenalkylsulfinyl , Cι~Cg- Alkylsulfonyl , Ci-Cg-Halogenalkylsulfonyl , Cι~Cg- Alkylcarbonyl, Ci-Cg-Halogenalkylcarbonyl, Cι~Cg-R 9 nitro, halogen, cyano, Ci-Cg-alkyl, Ci-Cg-haloalkyl, di- (Ci-Cg-alkoxy) -methyl, di- (C -Cg-alkyl-thio) -methyl, (Ci-Cg -Alkoxy) (Ci-Cg-alkylthio) - methyl, hydroxy, Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, Ci-Cg-alkylthio, Ci-Cg-haloalkylthio, C -C 6 - alkylsulfinyl, Ci-Cg- Halogenalkylsulfinyl, Cι ~ Cg- alkylsulfonyl, Ci-Cg-haloalkylsulfonyl, Cι ~ Cg- alkylcarbonyl, Ci-Cg-haloalkylcarbonyl, Cι ~ Cg-
Alkoxycarbonyl oder Ci-Cg-Halogenalkoxycarbonyl;Alkoxycarbonyl or Ci-Cg-haloalkoxycarbonyl;
oderor
zwei Reste R9 , die am gleichen Kohlenstoff gebunden sind, bilden gemeinsam eine -0- (CH )m-0- , -0- (CH2)m-S- , -S- (CH2)m-S- oder -0- (CH2) n _Kette, die durch einen bis drei Reste aus folgender Gruppe substituiert sein kann: Halogen, Cyano, C1-C4-Alkyl, C1-C4-Halogenalkyl oder C1-C4 -Alkoxycarbonyl;two radicals R 9 , which are bonded to the same carbon, together form a -0- (CH) m -0-, -0- (CH 2 ) m -S-, -S- (CH 2 ) mS- or -0 - (CH 2 ) n _ chain, which can be substituted by one to three radicals from the following group: halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 alkoxycarbonyl;
oderor
zwei Reste R9 , die am gleichen Kohlenstoff gebunden sind, bilden gemeinsam eine - (CH2) -Kette, die durch Sauerstoff oder Schwefel unterbrochen sein kann und/ oder durch einen bis vier Reste aus folgender Gruppe substituiert sein kann: Halogen, Cyano, C1-C4 -Alkyl, Ci -C4 -Halogenalkyl oder C1-C4 -Alkoxycarbonyl;two R 9 radicals which are bonded to the same carbon together form a - (CH 2 ) chain which can be interrupted by oxygen or sulfur and / or can be substituted by one to four radicals from the following group: halogen, cyano, C 1 -C 4 alkyl, Ci -C 4 haloalkyl or C 1 -C 4 alkoxycarbonyl;
oderor
zwei Reste R9 , die am gleichen Kohlenstoff gebunden sind, bilden gemeinsam eine Methylidengruppe, die durch einen bis zwei Reste aus folgender Gruppe substituiert sein kann:two radicals R 9 , which are bonded to the same carbon, together form a methylidene group which is formed by one or two radicals from the following group can be substituted:
Halogen, Hydroxy, Formyl , Cyano, Ci-Cg-Alkyl, Ci-Cg-Halogenalkyl, Ci-Cg-Alkoxy, Ci-Cg-Halogen- alkoxy, Ci-Cg-Alkylthio, Ci-Cg-Halogenalkylthio,Halogen, hydroxy, formyl, cyano, Ci-Cg-alkyl, Ci-Cg-haloalkyl, Ci-Cg-alkoxy, Ci-Cg-haloalkoxy, Ci-Cg-alkylthio, Ci-Cg-haloalkylthio,
Ci-Cg-Alkylsulfinyl, Ci-Cg-Halogenalkylsulfinyl , Ci-Cg-Alkylsulfonyl Ci-Cg-Halogenalkylsulfonyl ;Ci-Cg-alkylsulfinyl, Ci-Cg-haloalkylsulfinyl, Ci-Cg-alkylsulfonyl Ci-Cg-haloalkylsulfonyl;
oderor
zwei Reste R9 , die am gleichen Kohlenstoff gebunden sind, bilden gemeinsam mit diesem Kohlenstoff eine Carbonylgruppe aus ;two radicals R 9 which are bonded to the same carbon form a carbonyl group together with this carbon;
oderor
zwei Reste R9 , die an verschiedenen Kohlenstoffen gebunden sind, bilden gemeinsam eine - (CH2)n-Kette, die durch einen bis drei Reste aus folgender Gruppe substituiert sein kann:two R 9 radicals which are bonded to different carbons together form a - (CH 2 ) n chain which can be substituted by one to three radicals from the following group:
Halogen, Ci-Cg-Alkyl, Ci-Cg -Alkoxy, Hydroxy oder Ci-Cg-Alkoxycarbonyl ;Halogen, Ci-Cg-alkyl, Ci-Cg-alkoxy, hydroxy or Ci-Cg-alkoxycarbonyl;
Rio Ci-Cg-Alkyl, C3-Cg-Alkenyl, C3-Cg-Halogenalkenyl, C -Cg-Alkinyl, C3-Cg-Halogenalkinyl , C3-Cg-Cyclo- alkyl, Cι-C2o-Alkylcarbonyl, C2-Cg-Alkenylcarbonyl , C2-Cg-Alkinylcarbonyl , C3-Cg-Cycloalkylcarbonyl , Ci-Cg-Alkoxycarbonyl , C -Cg-Alkenyloxycarbonyl , C3-Cg-Alkinyloxycarbonyl, Ci-Cg-Alkylthiocarbonyl, Ci-Cg-Alkylaminocarbonyl, C-Cg-Alkenylaminocarbo- nyl, C3-Cg-Alkinylaminocarbonyl, N,N-Di- (Ci-Cg-alkyl) -aminocarbonyl, N- (C3-Cg-Alkenyl) -N- (Ci-Cg-alkyl) -aminocarbonyl, N- (C3-Cg-Alkinyl) -N- (Ci-Cg-alkyl) -aminocarbonyl, N- (Ci-Cg-Alkoxy) -N- (Ci-Cg-alkyl) -aminocarbonyl,Rio Ci-Cg-alkyl, C 3 -Cg-alkenyl, C 3 -Cg-haloalkenyl, C -Cg-alkynyl, C 3 -Cg-haloalkynyl, C 3 -Cg-cycloalkyl, -C-C 2 o-alkylcarbonyl , C 2 -Cg-alkenylcarbonyl, C 2 -Cg-alkynylcarbonyl, C 3 -Cg-cycloalkylcarbonyl, Ci-Cg-alkoxycarbonyl, C-Cg-alkenyloxycarbonyl, C 3 -Cg-alkynyloxycarbonyl, Ci-Cg-alkylthiocarbonyl, Ci-Cg -Alkylaminocarbonyl, C-Cg-Alkenylaminocarbonyl, C 3 -Cg-Alkynylaminocarbonyl, N, N-Di- (Ci-Cg-alkyl) -aminocarbonyl, N- (C 3 -Cg-Alkenyl) -N- (Ci- Cg-alkyl) -aminocarbonyl, N- (C 3 -Cg-alkynyl) -N- (Ci-Cg-alkyl) -aminocarbonyl, N- (Ci-Cg-alkoxy) -N- (Ci-Cg-alkyl) - aminocarbonyl,
N- (C -Cg-Alkenyl) -N- (Ci-Cg-alkoxy) -aminocarbonyl, N- (C -Cg-Alkinyl) -N- (Ci-Cg-alkoxy) -aminocarbonyl, Di- (Ci-Cg-alkyl) -aminothiocarbonyl , Cι~Cg-Alkylcar- bonyl-Ci-Cg-alkyl , Cι-Cg-Alkoxyimino-Cι-Cg-alkyl , N- (Ci-Cg-Alkylamino) -imino-Ci-Cg-alkyl oderN- (C -Cg-alkenyl) -N- (Ci-Cg-alkoxy) -aminocarbonyl, N- (C-Cg-alkynyl) -N- (Ci-Cg-alkoxy) -aminocarbonyl, di- (Ci-Cg -alkyl) -aminothiocarbonyl, Cι-Cg-alkylcarbonyl-Ci-Cg-alkyl, Cι-Cg-alkoxyimino-Cι-Cg-alkyl, N- (Ci-Cg-alkylamino) -imino-Ci-Cg-alkyl or
N, N-Di- (Ci-Cg-alkylamino) -imino-Ci-Cg-alkyl , wobei die genannten Alkyl-, Cycloalkyl- und Alkoxyreste partiell oder vollständig halogeniert sein können und/oder eine bis drei der folgenden Gruppen tra- gen können: Cyano, Cι-C4~Alkoxy, Cι-C4-Alkylthio, Di- (C1-C4- alkyl) -amino, Cι-C4~Alkylcarbonyl, Cι~C4-Alkoxy- carbonyl , Cι-C4-Alkoxy-Cι-C4~alkoxycarbonyl , Di- (Cι~C4-alkyl) -amino-Cι-C4-alkoxycarbonyl , Hydroxycarbonyl, Cι-C4-Alkylaminocarbonyl,N, N-Di- (Ci-Cg-alkylamino) -imino-Ci-Cg-alkyl, where the alkyl, cycloalkyl and alkoxy radicals mentioned can be partially or completely halogenated and / or carry one to three of the following groups can: Cyano, C ~ 4 alkoxy, Cι-C 4 -alkylthio, di (C 1 -C 4 - alkyl) amino, Cι-C ~ 4 alkylcarbonyl, Cι ~ C 4 alkoxy carbonyl, Cι-C 4 -Alkoxy-C 4 -alkoxycarbonyl, di- (C 1 -C 4 -alkyl) amino-C 1 -C 4 -alkoxycarbonyl, hydroxycarbonyl, C 1 -C 4 -alkylaminocarbonyl,
Di- (Cι~C4-alkyl) -aminocarbonyl , Aminocarbonyl , Cι-C4-Alkylcarbonyloxy oder C3-Cg-Cycloalkyl;Di (C 1 -C 4 -alkyl) aminocarbonyl, aminocarbonyl, C 1 -C 4 alkylcarbonyloxy or C 3 -Cg cycloalkyl;
Phenyl, Heterocyclyl, Phenyl-Ci-Cg-alkyl, Heterocy- clyl-C -Cg-alkyl, Phenylcarbonyl-Ci-Cg-alkyl , Hete- rocyclylcarbonyl-Cι-C5-alkyl, Phenylcarbonyl, Heterocyclylcarbonyl, Phenoxycarbonyl, Phenyloxythiocarbonyl, Heterocyclyloxycarbonyl, Heterocyclyl - oxythiocarbonyl, Phenylaminocarbonyl, N-(C ~Cg- Alkyl) -N- (phenyl) -aminocarbonyl , Heterocyclylami - nocarbonyl, N- (Ci-Cg-Alkyl) -N- (heterocyclyl) -aminocarbonyl, Phenyl-C2-Cg-alkenylcarbonyl oder Hetero- cyclyl-C2-Cg-alkenylcarbonyl, wobei der Phenyl- und der Heterocyclyl-Rest der 18 letztgenannten Sub- stituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann:Phenyl, heterocyclyl, phenyl-Ci-Cg-alkyl, heterocyclyl-C -Cg-alkyl, phenylcarbonyl-Ci-Cg-alkyl, heterocyclylcarbonyl-Cι-C 5 alkyl, phenylcarbonyl, heterocyclylcarbonyl, phenoxycarbonyl, phenyloxythiocarbonl, heterocycylyl , Heterocyclyl-oxythiocarbonyl, phenylaminocarbonyl, N- (C ~ Cg-alkyl) -N- (phenyl) -aminocarbonyl, heterocyclylami-nocarbonyl, N- (Ci-Cg-alkyl) -N- (heterocyclyl) -aminocarbonyl, phenyl-C 2 -Cg-alkenylcarbonyl or hetero-cyclyl-C 2 -Cg-alkenylcarbonyl, where the phenyl and heterocyclyl radicals of the 18 latter substituents can be partially or completely halogenated and / or can carry one to three of the following radicals:
Nitro, Cyano, Cι-C4~Alkyl, Cι-C4-Halogenalkyl, Cι~C4-Alkoxy oder Cι~C4-Halogenalkoxy;Nitro, cyano, C ~ 4 alkyl, Cι-C4 haloalkyl, Cι ~ C4 alkoxy or Cι ~ C 4 haloalkoxy;
R11, R12 Ci-Cg-Alkyl, C3-Cg-Alkenyl, C3-Cg-Halogenalkenyl, C3-Cg-Alkinyl, C3-Cg-Halogenalkinyl, C3-Cg-Cyclo- alkyl, Hydroxy, Ci-Cg-Alkoxy, Amino, C -Cg-Alkyl- amino, Ci-Cg-Halogenalkylamino, Di-(Cι~Cg- alkyDamino oder Di- (Ci-Cg-Halogenalkyl) amino, wobei die genannten Alkyl-, Cycloalkyl- und Alkoxyreste partiell oder vollständig halogeniert sein können und/oder eine bis drei der folgenden Gruppen tragen können: Cyano, Cι-C4-Alkoxy, Cι-C4-Alkylthio, Di- (C1-C4- alkyl) -amino, Cι-C4-Alkylcarbonyl, Cι-C4-Alkoxy- carbonyl , Cι-C4-Alkoxy-Cι-C4-alkoxycarbonyl, Di- (Cι~C4-alkyl) -amino-Cι-C4-alkoxycarbonyl, Hydroxycarbonyl , Cι-C4-Alkylaminocarbonyl , Di- (Cι~C4-alkyl) -aminocarbonyl, Aminocarbonyl,R 11 , R 12 Ci-Cg-alkyl, C 3 -Cg-alkenyl, C 3 -Cg-haloalkenyl, C 3 -Cg-alkynyl, C 3 -Cg-haloalkynyl, C 3 -Cg-cycloalkyl, hydroxy, Ci-Cg-alkoxy, amino, C -Cg-alkylamino, Ci-Cg-haloalkylamino, di- (Cι ~ Cg-alkyDamino or di- (Ci-Cg-haloalkyl) amino, the said alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and / or may carry one to three of the following groups: cyano, C 4 -alkoxy, C 4 alkylthio, di (C 1 -C 4 - alkyl) amino, Cι-C4-alkylcarbonyl, Cι-C 4 alkoxy carbonyl, Cι-C4-alkoxy-Cι-C4-alkoxycarbonyl, di (Cι ~ C4 alkyl) amino-Cι-C4-alkoxycarbonyl, Hydroxycarbonyl, C 1 -C 4 alkylaminocarbonyl, di (C 1 -C 4 alkyl) aminocarbonyl, aminocarbonyl,
Cι-C4-Alkylcarbonyloxy oder C3-Cg-Cycloalkyl;C 1 -C 4 -alkylcarbonyloxy or C 3 -Cg-cycloalkyl;
Phenyl, Heterocyclyl, Phenyl-Ci-Cg-alkyl , Heterocy- clyl-Ci-Cg-alkyl, Phenoxy, Heterocyclyloxy, wobei der Phenyl- und der Heterocyclyl-Rest der letztge- nannten Substituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann:Phenyl, heterocyclyl, phenyl-Ci-Cg-alkyl, heterocyclyl-Ci-Cg-alkyl, phenoxy, heterocyclyloxy, the phenyl and heterocyclyl radicals being the last mentioned substituents can be partially or completely halogenated and / or can carry one to three of the following radicals:
Nitro, Cyano, C -C4-Alkyl, Cι-C4-Halogenalkyl , Cι-C4-Alkoxy oder Cι~C4-Halogenalkoxy;Nitro, cyano, C -C 4 -alkyl, C 4 haloalkyl, Cι-C 4 alkoxy or Cι ~ C 4 haloalkoxy;
R13 Ci-C -Alkyl, C3-Cg-Alkenyl, C3 -Cg-Halogenalkenyl , C -Cg-Alkinyl, C3 -Cg-Halogenalkinyl , C3-Cg-Cyclo- alkyl, Hydroxy, Ci-Cg-Alkoxy, C3 -Cg-Alkenyloxy, C3-Cg-Alkinyloxy, Amino, Ci-Cg -Alkylamino,R 13 Ci-C-alkyl, C 3 -Cg alkenyl, C 3 -Cg haloalkenyl, C -Cg alkynyl, C 3 -Cg haloalkynyl, C 3 -Cg cycloalkyl, hydroxy, Ci-Cg- Alkoxy, C 3 -Cg-alkenyloxy, C 3 -Cg-alkynyloxy, amino, Ci-Cg -alkylamino,
Di- (Ci-Cg -Alkyl) -amino oder C -Cg-Alkylcarbonyl- amino, wobei die genannten Alkyl-, Cycloalkyl- und Alkoxyreste partiell oder vollständig halogeniert sein können und/oder einen bis drei Reste der fol- genden Gruppe tragen können:Di- (Ci-Cg-alkyl) -amino or C -Cg-alkylcarbonylamino, where the alkyl, cycloalkyl and alkoxy radicals mentioned can be partially or completely halogenated and / or can carry one to three radicals from the following group :
Cyano, Cι-C4-Alkoxy, C1-C4 -Alkylthio,Cyano, -CC 4 alkoxy, C 1 -C 4 alkylthio,
Di- (Cι-C4-alkyl) -amino, C1-C4 -Alkylcarbonyl ,Di- (Cι-C4 alkyl) amino, C 1 -C 4 alkylcarbonyl,
Ci -C4 -Alkoxycarbonyl , Ci -C4 -Alkoxy-C -C4 - alkoxy- carbonyl, Di- (C1-C4- alkyl) - amino -C1-C4- alkoxy- carbonyl, Hydroxycarbonyl, C1-C4-Alkylamino- carbonyl, Di- (C1-C4- alkyl) -aminocarbonyl, Aminocarbonyl, Cι-C4-Alkylcarbonyloxy oder C3-Cg-Cyclo- alkyl ;Ci -C 4 alkoxycarbonyl, Ci -C 4 alkoxy-C -C 4 alkoxycarbonyl, di- (C 1 -C 4 alkyl) - amino -C 1 -C 4 alkoxycarbonyl, hydroxycarbonyl, C 1 -C 4 alkylamino carbonyl, di (C 1 -C 4 alkyl) aminocarbonyl, aminocarbonyl, C 1 -C 4 alkylcarbonyloxy or C 3 -Cg cycloalkyl;
Phenyl, Heterocyclyl, Phenyl -Ci-Cg- alkyl oder Hete- rocyclyl-C -Cg- alkyl, wobei der Phenyl- oder Heterocyclyl-Rest der vier letztgenannten Substituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann:Phenyl, heterocyclyl, phenyl-Ci-Cg-alkyl or heterocyclyl-C-Cg-alkyl, where the phenyl or heterocyclyl radical of the four last-mentioned substituents can be partially or completely halogenated and / or carry one to three of the following radicals can:
Nitro, Cyano, C1-C4 -Alkyl, C1-C4-Halogenalkyl, Cι-C4-Alkoxy oder C1-C4 -Halogenalkoxy;Nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, Cι-C 4 -alkoxy or C 1 -C 4 -haloalkoxy;
Rl4 Ci-Cg-Alkyl, C3-Cg-Alkenyl, C3 -Cg -Alkinyl oder Ci-Cg-Alkylcarbonyl;Rl 4 Ci-Cg-alkyl, C 3 -Cg-alkenyl, C 3 -Cg -alkynyl or Ci-Cg-alkylcarbonyl;
q 0 bis 6q 0 to 6
sowie deren landwirtschaftlich brauchbaren Salze.and their agriculturally useful salts.
2. Cyclohexenondioxothiochromanoyl-Derivate der Formel I, gemäß Anspruch 1, wobei2. Cyclohexenone dioxothiochromanoyl derivatives of formula I, according to claim 1, wherein
R9 Nitro, Halogen, Cyano, Ci-Cg-Alkyl, Ci-Cg-Halogen- alkyl, Di - (Ci-Cg-alkoxy) -methyl , Di - (Ci-Cg-alkyl - thio) -methyl, (Ci-Cg-Alkoxy) (Ci -Cg -alkylthio) -methyl, Hydroxy, Ci-Cg -Alkoxy, Ci-Cg-Halogenalkoxy, Ci-Cg-Alkylthio, Ci-Cg-Halogenalkylthio, Ci-Cg-Al- kylsulfinyl, Ci -Cg -Halogenalkylsulfinyl, Ci-Cg-Al- kylsulfonyl, Ci -Cg -Halogenalkylsulfonyl, C -Cg-Al- kylcarbonyl, Ci-Cg-Halogenalkylcarbonyl, Ci-Cg-Alk- oxycarbonyl oder Ci-Cg-Halogenalkoxycarbonyl;R 9 nitro, halogen, cyano, Ci-Cg-alkyl, Ci-Cg-halogeno-alkyl, di - (Ci-Cg-alkoxy) -methyl, di - (Ci-Cg-alkyl - thio) -methyl, (Ci -Cg-alkoxy) (Ci -Cg -alkylthio) -methyl, hydroxy, Ci-Cg -alkoxy, Ci-Cg-haloalkoxy, Ci-Cg-alkylthio, Ci-Cg-haloalkylthio, Ci-Cg-alkylsulfinyl, Ci-Cg -haloalkylsulfinyl, Ci-Cg-alkylsulfonyl, Ci-Cg -haloalkylsulfonyl, C -Cg-alkylcarbonyl, Ci- Cg-haloalkylcarbonyl, Ci-Cg-alkoxycarbonyl or Ci-Cg-haloalkoxycarbonyl;
bedeutetmeans
oderor
zwei Reste R9 , die am gleichen Kohlenstoff gebunden sind, bilden gemeinsam eine -0- (CH2)m-0- , -0- (CH2) m- S - , -S- (CH2.m-S- oder -0- (CH2) n-Kette, die durch einen bis drei Reste aus folgender Gruppe substituiert sein kann:two radicals R 9 which are bonded to the same carbon together form a -0- (CH 2 ) m -0-, -0- (CH 2 ) m - S -, -S- (CH 2. m -S- or -0- (CH 2 ) n chain, which can be substituted by one to three radicals from the following group:
Halogen, Cyano, Cι-C4-Alkyl, C -C4 -Halogenalkyl oder C1-C4 -Alkoxycarbonyl;Halogen, cyano, -CC 4 alkyl, C -C 4 haloalkyl or C 1 -C 4 alkoxycarbonyl;
oderor
zwei Reste R9, die am gleichen Kohlenstoff gebunden sind, bilden eine - (CH2)p-Kette, die durch Sauerstoff oder Schwefel unterbrochen sein kann und/oder durch einen bis vier Reste aus folgender Gruppe substituiert sein kann:two R 9 radicals which are bonded to the same carbon form a - (CH 2 ) p chain which can be interrupted by oxygen or sulfur and / or can be substituted by one to four radicals from the following group:
Halogen, Cyano, C1-C4-Alkyl, C1-C4-Halogenalkyl oder C1-C4 -Alkoxycarbonyl ;Halogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or C 1 -C 4 alkoxycarbonyl;
oderor
zwei Reste R9 , die am gleichen Kohlenstoff gebunden sind, bilden gemeinsam mit diesem Kohlenstoff eine Carbonylgruppe aus .two radicals R 9 , which are bonded to the same carbon, form a carbonyl group together with this carbon.
3. Verfahren zur Herstellung von Verbindungen der Formel I gemäß den Ansprüchen 1 oder 2 mit R8 = Halogen, dadurch gekenn¬ zeichnet, daß man ein Cyclohexandion-Derivat der Formel III,3. A process for the preparation of compounds of formula I according to claims 1 or 2 with R 8 = halogen, characterized ¬ characterized in that a cyclohexanedione derivative of the formula III,
wobei die Variablen R1 bis R9, X, 1, q die in den Ansprüchen 1 oder 2 genannte Bedeutung haben, mit einem Halogenierungs- mittel umsetzt. where the variables R 1 to R 9 , X, 1, q have the meaning given in claims 1 or 2, are reacted with a halogenating agent.
4. Verfahren zur Herstellung von Verbindungen der Formel I gemäß den Ansprüchen 1 oder 2 mit R8 = OR10, OS02Rn, OPOR^R12 oder OPSRι:LR12 dadurch gekennzeichnet, daß man ein Cyclohexandion- Derivat der Formel III,4. A process for the preparation of compounds of formula I according to claims 1 or 2 with R 8 = OR 10 , OS0 2 R n , OPOR ^ R 12 or OPSR ι: L R 12, characterized in that a cyclohexanedione derivative of the formula III,
wobei die Variablen R1 bis R9, X, 1, q die in den Ansprüchen 1 oder 2 genannte Bedeutung haben, mit einer Verbindung der Formel IVα, IVß, IVγ oder IVδ,where the variables R 1 to R 9 , X, 1, q have the meaning given in claims 1 or 2, with a compound of the formula IVα, IVß, IVγ or IVδ,
Li - R" L1 - S02R11 L1 - POR11R12 L^ PSRUR12 Li - R "L 1 - S0 2 R 11 L 1 - POR 11 R 12 L ^ PSR U R 12
wobei die Variablen R10 bis R12 die in den Ansprüchen 1 oder 2 genannte Bedeutung haben und L1 für eine nucleophil verdräng- bare Abgangsgruppe steht, umsetzt.where the variables R 10 to R 12 have the meaning given in claims 1 or 2 and L 1 represents a nucleophilically displaceable leaving group.
5. Verfahren zur Herstellung von Verbindungen der Formel I gemäß den Ansprüchen 1 oder 2 mit R8 = OR10, SR10, POR1:LR12, NR13R14, ONR14R14, N-gebundenes Heterocyclyl oder 0 (N-gebundenes Heterocyclyl) , dadurch gekennzeichnet, daß man eine Verbindung der Formel Iα (≡ I mit R8 = Halogen, OS0R1:L) ,5. A process for the preparation of compounds of formula I according to claims 1 or 2 with R 8 = OR 10 , SR 10 , POR 1: L R 12 , NR 13 R 14 , ONR 14 R 14 , N-linked heterocyclyl or 0 ( N-linked heterocyclyl), characterized in that a compound of the formula Iα (≡ I with R 8 = halogen, OS0R 1: L ),
gen, OSO2R11 gen, OSO 2 R 11
wobei die Variablen R1 bis R3, R9 und R11, X, 1, q die in den Ansprüchen 1 oder 2 genannte Bedeutung haben, mit einer Verbindung der Formel Vα, Vß, Vγ, vδ, Vε, Vη oder Vθ, HORl° HSRl° HPOR11R12 HNRl3Rl HONRl Rl« vα vß vγ Vδ vεwhere the variables R 1 to R 3 , R 9 and R 11 , X, 1, q have the meaning given in claims 1 or 2, with a compound of the formula Vα, Vß, Vγ, vδ, Vε, Vη or Vθ, HORl ° HSR l ° HPOR 11 R 12 HNR l3 R l HONR l R l «vα vß vγ Vδ vε
H (N-gebundenes HO (N-gebundenes Heterocyclyl) Heterocyclyl)H (N-linked HO (N-linked heterocyclyl) heterocyclyl)
Vη Vθ,Vη Vθ,
wobei die Variablen R10 bis R14 die in den Ansprüchen 1 oder 2 genannte Bedeutung haben, gegebenenfalls in Gegenwart einer Base umsetzt.where the variables R 10 to R 14 have the meaning given in claims 1 or 2, optionally in the presence of a base.
6. Verfahren zur Herstellung von Verbindungen der Formel I gemäß den Ansprüchen 1 oder 2 mit R8 = SOR11, S02Rn, dadurch gekennzeichnet, daß man eine Verbindung der Formel Iß (≡ I mit R8 = SR10) ,6. A process for the preparation of compounds of the formula I according to claims 1 or 2 with R 8 = SOR 11 , S0 2 R n , characterized in that a compound of the formula Iß (≡ I with R 8 = SR 10 ),
wobei die Variablen R1 bis R3, R9 , R°, X, 1, q die in den Ansprüchen 1 oder 2 genannte Bedeutung haben, mit einem Oxidationsmittel umsetzt. wherein the variables R 1 to R 3 , R 9 , R °, X, 1, q have the meaning given in claims 1 or 2, reacted with an oxidizing agent.
7. Mittel, enthaltend eine herbizid wirksame Menge mindestens eines Cyclohexenondioxothiochromanoyl-Derivates der Formel I oder eines landwirtschaftlich brauchbaren Salzes von I gemäß den Ansprüchen 1 oder 2, und für die Formulierung von Pflanzenschutzmitteln übliche Hilfsmittel.7. Agent containing a herbicidally effective amount of at least one cyclohexenone dioxothiochromanoyl derivative of the formula I or an agriculturally useful salt of I according to claims 1 or 2, and auxiliaries customary for the formulation of crop protection agents.
8. Verfahren zur Herstellung von Mitteln gemäß Anspruch 7, dadurch gekennzeichnet, daß man eine herbizid wirksame Menge mindestens eines Cyclohexenondioxothiochromanoyl-Derivates der Formel I oder eines landwirtschaftlich brauchbaren Salzes von I gemäß den Ansprüchen 1 oder 2 und für die Formulierung von Pflanzenschutzmitteln übliche Hilfsmittel mischt.8. A process for the preparation of compositions according to claim 7, characterized in that mixing a herbicidally effective amount of at least one cyclohexenone dioxothiochromanoyl derivative of the formula I or an agriculturally useful salt of I according to claims 1 or 2 and auxiliaries customary for the formulation of crop protection agents .
9. Verfahren zur Bekämpfung von unerwünschtem Pflanzenwuchs, dadurch gekennzeichnet, daß man eine herbizid wirksame Menge mindestens eines Cyclohexenondioxothiochromanoyl-Derivates der Formel I oder eines landwirtschaftlich brauchbaren Salzes 9. A method for controlling unwanted vegetation, characterized in that a herbicidally effective amount of at least one cyclohexenone dioxothiochromanoyl derivative of the formula I or an agriculturally useful salt
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CN1235898C (en) 2006-01-11
JP2002513788A (en) 2002-05-14
AU4032099A (en) 1999-11-23
WO1999057111A1 (en) 1999-11-11
AU764645B2 (en) 2003-08-28
AR016246A1 (en) 2001-06-20
TW585860B (en) 2004-05-01
WO1999057111A9 (en) 2001-03-01
CN1307572A (en) 2001-08-08
US6440899B1 (en) 2002-08-27
IL139276A0 (en) 2001-11-25
CA2330585A1 (en) 1999-11-11

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