WO2000059910A2 - Tricyclic pyrazolone derivatives - Google Patents

Tricyclic pyrazolone derivatives Download PDF

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WO2000059910A2
WO2000059910A2 PCT/EP2000/002564 EP0002564W WO0059910A2 WO 2000059910 A2 WO2000059910 A2 WO 2000059910A2 EP 0002564 W EP0002564 W EP 0002564W WO 0059910 A2 WO0059910 A2 WO 0059910A2
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alkyl
alkoxy
cyano
hydrogen
halogen
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PCT/EP2000/002564
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German (de)
French (fr)
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WO2000059910A3 (en
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Klaus Langemann
Ernst Baumann
Wolfgang Von Deyn
Steffen Kudis
Guido Mayer
Ulf Misslitz
Ulf Neidlein
Matthias Witschel
Thorsten Volk
Martina Otten
Karl-Otto Westphalen
Helmut Walter
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Basf Aktiengesellschaft
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Priority to AU42901/00A priority Critical patent/AU4290100A/en
Publication of WO2000059910A2 publication Critical patent/WO2000059910A2/en
Publication of WO2000059910A3 publication Critical patent/WO2000059910A3/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Definitions

  • the present invention relates to new tricyclic pyrazolone derivatives with herbicidal activity, processes for the preparation of the tricyclic pyrazolone derivatives, agents which contain them and the use of these derivatives or agents comprising weeds for combating weeds.
  • Herbicidal tricyclic pyrazolone derivatives are known from the literature, for example from WO 97/19087.
  • the task was to find new tricyclic pyrazolone derivatives with improved properties.
  • R 1 is hydrogen, C * ⁇ -C 6 -alkyl, C 6 haloalkyl,
  • R 2 is hydrogen, -CC 6 -alkyl, -C-C 6 -alkoxy, -C-C 6 -haloalkyl, -C-C 6 -haloalkoxy, optionally with
  • R 3 , R 4 are hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio,
  • C ⁇ -C6 haloalkylthio C ⁇ -C 6 alkylsulfinyl, C ⁇ -C 6 -Halo- alkylsulfinyl, C ⁇ -C 6 alkylsulfonyl, C ⁇ -C 6 haloalkyl sulfonyl, NR 7 R 8, C 2 -C 6 - Alkoxyalkyl, -CC 6 alkoxy carbonyl, -C 6 -alkyicarbonyl, halogen, cyano, nitro, optionally with C ⁇ -C 3 alkyl, halogen, cyano or
  • R 5 is hydrogen or C 1 -C 4 alkyl
  • R 6 is hydrogen, -CC 6 alkyl or halogen
  • R 7 is hydrogen or iC 6 alkyl
  • R 8 Ci-C 6 alkyl or -CC 6 alkoxy
  • R 9 is a residue Ha or Ilb
  • i4 -CC 6 alkyl C 3 -C 6 alkenyl, C 3 -C 6 alkynyl or C 3 -C 6 cycloalkyl, where the four radicals mentioned can be partially or completely halogenated and / or one to three of the can carry the following groups: cyano, C 4 alkoxy, C 1 -C 4 haloalkoxy, C ⁇ -C 4 alkylthio, C ⁇ -C4-haloalkylthio, C ⁇ -C 4 alkyl carbonyl, C 1 -C 4 -Alkoxycarbonyl or -CC 4 -haloalkoxycarbonyl;
  • Ris. R16 is hydrogen, hydroxy, C ⁇ -C east -alkyl, C 6 alkoxy, Ci-C ⁇ alkylthio, phenyl, phenyl-C 1 -C 4 alkyl or phenoxy, where the three last-mentioned substituents partially or fully halogenated can be and / or may carry one to three of the following radicals: nitro, cyano, C 4 alkyl, halo-Ci-C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 -haloalkoxy or Ci -C 4 alkoxycarbonyl;
  • R 17 is hydrogen, -CC 6 alkyl, C 3 -C 6 alkenyl,
  • herbicidal compositions which contain the compounds I and have a very good herbicidal action.
  • processes for the preparation of these compositions and processes for controlling unwanted vegetation using the compounds I have been found.
  • the compounds of the formula I can contain one or more centers of chirality and are then present as enantiomers or mixtures of diastereomers.
  • the invention relates both to the pure enantiomers or diastereomers and to their mixtures.
  • the compounds of the formula I can also be present in the form of their agriculturally useful salts, the type of salt generally not being important. 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 ⁇ - be hydroxy-C ⁇ -C alkyl, C ⁇ -C4-alkoxy-C ⁇ -C4-alkyl, hydroxy-C ⁇ -C4-alkoxy-C ⁇ -C replaced 4 alkyl, phenyl or benzyl C 4 alkyl can, preferably ammonium, dimethylammonium, diisopropylammonium, tetramethylammonium, tetrabutylammonium, 2- (2-hydroxy-eth-1-oxy) eth-1-ylammonium, di (2-hydroxyeth-1-yl) ammonium, trimethylbenzylammonium, further phosphonium ions, sulfon
  • 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.
  • Ilb also represent the tautomeric forms Ilb 'and Ilb' '.
  • C 1 -C 4 alkyl and the alkyl parts of phenyl -C 1 -C 4 alkyl and heterocyclyl -C 1 -C 4 alkyl: for example methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2nd -Methylpropyl or 1, 1-dimethylethyl;
  • Ci-C ⁇ - alkyl as well as the alkyl parts of C * ⁇ -C 6 -alkoxyimino-C ⁇ -C 6 - alkyl, N-C ⁇ -C 6 -alkoxy-N-C ⁇ -C 6 -alkylamino, N (C 1 - C 6 -alkoxy) -N- (C ⁇ -C 6 -alkyl) -aminocarbonyl, N- (C 3 -C 6 -alkenyl) -N- (Ci-C ⁇ -alkyl) -aminocarbonyl, (C 3 -C 6 -alkynyl) -N- (Ci-C ⁇ - alkyl) -aminocarbonyl, N- (Ci-C ⁇ - alkyl) -N-phenyla-minocarbonyl, N- (Ci-C ⁇ -alkyl) -N -heterocyclylaminocarbonyl, phenyl
  • C 1 -C 4 -alkyl as mentioned above, and for example pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2, 2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-dimethylpropyl, 1,2 -Dirnethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1,3-dimethylbutyl, 2, 2-dimethylbutyl, 2, 3-dimethylbutyl , 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1-ethyl-l-methylpropyl or 1-ethyl-3-methylpropyl;
  • C 1 -C 4 -haloalkyl a C ⁇ -C 4 -alkyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and / or iodine, eg chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl , Chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2, 2-difluoroethyl, 2, 2, 2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro -2, 2-difluoroethyl, 2, 2-dichloro-2-fluoroethyl, 2, 2, 2-trichloroethyl, pentafluoroethyl, 2-fluoroprop
  • -C-C 4 alkoxy for example methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1, 1-dimethylethoxy;
  • N-C 1 -C 6 -alkoxy and the alkoxy parts of N-C 1 -C 6 -alkoxyamino, di- (C 1 -C 6 -alkoxy) methyl, (C 1 -C 6 -alkoxy) (C 1 -C 6 -alkylthio) - methyl , -CC 6 alkoxyimino -C 6 alkyl, N -C -C 6 alkoxy- N-Ci-C ⁇ -alkylamino, N- (-C 6 alkoxy) -N- (Ci-C ⁇ -alkyl) -amino-carbonyl, N- (C 3 -C 6 -alkenyl) -N- (Ci-Ce-alkoxy) -aminocarbonyl and N- (C 3 -C 6 -alkynyl) -N- (Ci-C ⁇ -alkoxy) -aminocarbonyl:
  • C ⁇ -C 4 -haloalkoxy a -CC alkoxy, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2nd -Fluoroethoxy, 2-chloroethoxy, 2-bromomethoxy, 2-iodoethoxy, 2, 2-difluoroethoxy, 2, 2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2, 2-difluoroethoxy, 2,2 -Dichloro-2-fluoroethoxy, 2,2, 2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy, 3-ch
  • Ci-C ß -haloalkoxy -C-C4-haloalkoxy, as mentioned above, and for example 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or dodecafluorohexoxy;
  • C 1 -C 4 ⁇ alkylthio for example methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio or 1, 1-dimethylethylthio;
  • Ci-C ⁇ - alkylthio and the alkylthio parts of C ⁇ -C 6 -alkylthiocarbonyl, di- (C ⁇ -C 6 -alkylthio) methyl and (C ⁇ -C 6 -alkoxy) (Ci-C ⁇ -alkylthio) methyl: C ⁇ -C 4- alkylthio, as mentioned above, and for example pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2, 2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1, 1-dimethylpropylthio, 1 , 2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio,
  • C 1 -C 4 haloalkylthio a C 1 -C 4 -alkylthio radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, bromodifluoromethylthio , 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2, 2-difluoroethylthio, 2, 2, 2-trifluoroethylthio, 2,2,2-trichloroethylthio, 2-chloro-2-fluoroethylthio, 2 -Chlor-2,2-difluoroethylthio, 2, 2-dichloro-2-fluoroethylthio, pentafluoroe
  • methylsulfinyl ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl or 1, 1- Dimethylethylsulfinyl;
  • C ⁇ ⁇ C4-haloalkylsulfinyl which is C ⁇ ⁇ C4-alkylsulfinyl as mentioned above partially or fully substituted by fluorine, chlorine, bromine and / or iodine, eg fluoromethylsulfinyl, ethylsulfinyl difluoro, trifluoromethyl - sulfinyl, chlorodifluoromethylsulfinyl, Bromdifluormethylsulfi- nyl, 2-fluoroethylsulfinyl, 2-chloroethylsulfinyl, 2-bromoethylsulfinyl, 2-iodoethylsulfinyl, 2,2-difluoroethylsulfinyl, 2,2, 2-trifluoroethylsulfinyl, 2,2, 2-trichloroethylsulfinyl
  • C * ⁇ -C 4 -haloalkylsulfonyl a C 1 -C 4 -alkylsulfonyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and / or iodine, eg fluoromethylsulfonyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, Chlordifluormethylsulfonyl, Bromdifluormethylsulfo - nyl, 2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl, 2, 2-difluoroethylsulfonyl, 2, 2, 2-trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfony
  • Ci-C ⁇ -haloalkylsulfonyl C ⁇ -C 4 -haloalkylsulfonyl as mentioned above, and 5-fluoropentylsulfonyl, 5-chloropentylsulfonyl, 5-bromopentylsulfonyl, 5-iodopentylsulfonyl, 6-fluorhexylsulfonyl, 6-bromhexyl-sulfonyl-hexylsulfonyl; Ci-C ⁇ -alkylamino: e.g.
  • Di- (-C-alkyl) amino e.g. 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-methylpropyl) amino , N- (1, 1-dimethylethyl) -N-methylamino, N-ethyl-N-
  • Di- (CI-C ⁇ alkyl) amino di- (C 1 -C 4 alkyl) amino as mentioned above, and also N, N-dipentylamino, N, N-dihexylamino, N-methyl-N-pentylamino, N -Ethyl-N-pentylamino, N-methyl-N-hexylamino or N-ethyl-N-hexylamino.
  • C 1 -C 4 -alkylcarbonyl for example methylcarbonyl, ethylcarbonyl, propylcarbonyl, 1-methylethylcarbonyl, butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl or 1, 1-dimethylethylcarbonyl;
  • Ci-C ⁇ alkylcarbonyl 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-Dirnethylpropylcarbonyl,
  • C ⁇ -C4-haloalkylcarbonyl a C1-C4 alkylcarbonyl as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and / or iodine, ie, for example chloroacetyl, dichloroacetyl, trichloroacetyl, fluoroacetyl, difluoroacetyl, trifluoroacetyl , Chlorofluoroacetyl, dichlorofluoracetyl, chlorodifluoroacetyl, 2-fluoroethylcarbonyl, 2-chloroethylcarbonyl, 2-bromoethylcarbonyl, 2-iodoethylcarbonyl, 2, 2-difluoroethylcarbonyl, 2,2, 2-trifluoroethylcarbonyl, 2-chloro-2-fluoroethylcarbonyl, 2 Chloro-2,2-difluor
  • Ci-C ö -haloalkylcarbonyl a C ⁇ -C 4 -haloalkylcarbonyl radical as mentioned above, and 5-fluoropentylcarbonyl, 5-chloropentylcarbonyl, 5-bromopentylcarbonyl, perfluoropentylcarbonyl, 6-fluorhexylcarbonyl, 6 -chlorohexylcarbonyl, 6-bromo-hexylcarbonyl or perfluorohexylcarbonyl;
  • C 1 -C 4 alkoxycarbonyl and the alkoxycarbonyl parts of di- (-C 4 -alkyl) amino -CC-C 4 -alkoxycarbonyl, ie for example methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, 1-methylethoxycarbonyl, butoxycarbonyl, 1st -Methylpropoxycarbonyl, 2-methyl-propoxycarbonyl or 1, 1-Dirnethylethoxycarbonyl; (Ci-Cg-alkoxy) carbonyl: (-C ⁇ C -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,
  • C ⁇ -C4-haloalkoxycarbonyl a C ⁇ -C4-alkoxycarbonyl as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and / or iodine, eg Fluormethoxycarbonyl, Difluormethoxycarbonyl, xycarbonyl Trifluormetho-, Chlordifluormethoxycarbonyl, bromodifluoromethoxy carbonyl, 2-fluoroethoxycarbonyl, 2-chloroethoxycarbonyl,
  • C 1 -C 6 haloalkoxycarbonyl a C 1 -C 4 haloalkoxycarbonyl radical as mentioned above, and 5-fluoropentoxycarbonyl, 5 -chloropentoxycarbonyl, 5-bromopentoxycarbonyl, 6 -fluoro-hexoxycarbonyl, 6-chlorohexoxycarbonyl or 6-bromohexoxycarbonyl or ;
  • (-C-C 4 ⁇ alkyl) carbonyloxy acetyloxy, ethylcarbonyloxy, ' propyl - carbonyloxy, 1-methylethylcarbonyloxy, butylcarbonyloxy, 1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy or 1, 1-dimethylethylcarbonyloxy;
  • (-C-C 4 alkylamino) carbonyl for example methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl, 1-methylethylaminocarbonyl, B tylaminocarbonyl, 1-methylpropylaminocarbonyl, 2-methylpropylaminocarbonyl or 1, 1-dirnethylethylaminocarbonyl;
  • (Ci-C ⁇ -alkylamino) carbonyl (-C-C-alkylamino) carbonyl, as mentioned above, and e.g. Pentylaminocarbonyl, 1-methyl-b tylaminocarbonyl, 2-methylb tylaminocarbonyl, 3-methylbutylaminocarbonyl, 2, 2-dimethylpropylaminocarbonyl, 1-ethylpropylaminocarbonyl, hexylaminocarbonyl, 1, 1-dimethylpropyla- minocarbonyl, 1,2-dimethylpropamin Methylpentylaminocarbonyl, 2-methylpentylaminocarbonyl, 3-methylpentylaminocarbonyl, 4-methylpentylaminocarbonyl, 1, 1-dimethylbutylaminocarbonyl, 1, 2-dimethylbutylaminocarbonyl, 1, 3-dimethylbutylaminocarbonyl, 2, 2-dimethylbutylamino
  • Di- (-C-alkyl) aminocarbonyl e.g. N, N-dimethylaminocarbonyl, N, N-diethylaminocarbonyl, N, N-di- (1-methylethyl) aminocarbonyl, N, N-dipropylaminocarbonyl, N, N-dibutylaminocarbonyl, N, N-di- (1-methylpropyl) -aminocarbonyl, N, N-di- (2-methyl-propyl) -aminocarbonyl, N, N-di- (1, 1-dimethylethyl) -aminocarbonyl, N-ethyl-N-methylaminocarbonyl, N-methyl-N-propyla - minocarbonyl, N-methyl-N- (1-methylethyl) aminocarbonyl, NB - tyl-N-methylaminocarbonyl, N-methyl-N- (1-methylpropy
  • Di- (Ci-C ⁇ -alkyl) -aminocarbonyl di- (-C-C 4 -alkyl) -amino-carbonyl, as mentioned above, and for example N-methyl-N-pentylaminocarbonyl, N-methyl-N- (1- methylbutyl) aminocarbonyl, N-methyl-N- (2-methylb tyl) aminocarbonyl, N-methyl-N- (3-methylbutyl) aminocarbonyl, N-methyl-N- (2,2-dimethylpropyl) aminocarbonyl, N-methyl-N- (1-ethylpropyl) aminocarbonyl, N-methyl-N-hexylaminocarbonyl, N-methyl-N- (1,1-dimethylpropyl) aminocarbonyl, N-methyl-N- (1,2 dimethylpropyl) aminocarbonyl, N-methyl-N- (1-methylpentyl) aminocarbonyl, N-methyl-N- (2-methylp
  • Di- (Ci-C ⁇ -alkyl) -ammothiocarbonyl e.g. N, N-dimethylaminothiocarbonyl, N, N-diethylaminothiocarbonyl, N, N-di- (1-methylethyl) ammothiocarbonyl, N, N-dipropylaminothiocarbonyl, N, N-dibutylaminothiocarbonyl, N, N-di- (1-methylpropyl) -amino-thiocarbonyl, N, N-di- (2-methylpropyl) -aminothiocarbonyl, N, N-di- (1, 1-dimethylethyl) -aminothiocarbonyl, N-ethyl-N-methylaminothiocarbonyl, N-methyl-N -propylaminothiocarbonyl, N-methyl-N- (1-methylethyl) -amino
  • C 3 -C 6 alkenylaminocarbonyl N- (C 3 -C 6 alkenyl) -N- (C ⁇ -C 6 ) alkyl - aminocarbonyl, N- (C 3 -C ⁇ - alkenyl) -N- (C ⁇ -C 6- alkoxy) aminocarbonyl: for example prop-2-en-1-yl, but-1-en-4-yl, 1-methyl-prop-2-en-1-yl, 2-methyl-prop-2-ene -l-yl, 2-butene-l-yl, l-penten-3-yl, l-penten-4-yl, 2-penten-4-yl, 1-methyl-but-2-en-l-yl , 2-methyl-but-2-en-l-yl, 3-methyl-but-2-en-l-yl, l-methyl-but-3-en-l-yl, 2-methyl-but-3 -en-1-yl, 3-methyl-but-3-en-1-yl, 1, 1-d
  • C 3 -C 6 haloalkenyl a C 3 -C 6 alkenyl radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example 2-chloroallyl, 3-chlorallyl, 2, 3-dichlorallyl, 3, 3-dichlorallyl, 2,3,3-trichlorallyl, 2, 3-dichlorobut-2-enyl, 2-bromoallyl, 3-bromoallyl, 2, 3-dibromoallyl, 3, 3-dibromoallyl, 2, 3, 3-tribromoallyl or 2,3-dibromobut-2-enyl;
  • C 3 -C 6 alkynyl and the alkynyl parts of C 3 -C 6 alkynylcarbonyl, C 3 -C 6 alkynyloxy, C 3 -C6 alkynyloxycarbonyl, C 3 -C 6 alkynylaminocarbonyl, N- ( C 3 -C 6 alkynyl) -N- (-C-C 6 -alkyl) -aminocarbonyl, N- (C 3 -C 6 -alkynyl) -N- (-C-C 6 -alkoxy-aminocarbonyl: for example propargyl, but -l-in-3-yl, but-l-in-4-yl, but-2-in-l-yl, pent-l-in-3-yi, pent-l-in-4-yl, pent -1-in-5-yl, pent-2-in-1-yl, pent-2-in-4-yl, pent
  • CC ⁇ alkynyl and the alkynyl parts of C 6 -C 6 alkynylcarbonyl: CC 6 alkynyl, as mentioned above, and ethynyl;
  • C 3 -C 6 haloalkynyl a C 3 -C 6 alkynyl radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example 1,1-difluoroprop-2- in-l-yl, 3-iodo-prop-2-in-l-yl, 4-fluorobut-2-in-l-yl, 4-chlorobut-2-in-l-yl, 1, 1-difluorobut- 2-in-l-yl, 4-iodobut-3-in-l-yl, 5-fluoropent-3-in-l-yl, 5-iodo-pent-4-in-l-yl, 6- Fluoro-hex-4-in-1-yl or 6-iodo-hex-5-in-1-yl;
  • C 3 -C 6 cycloalkyl and the cycloalkyl parts of C 3 -C 6 cycloalkylcarbonyl: for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;
  • heterocyclyl and also heterocyclyl parts of heterocyclylcarbonyl, heterocyclyl-Ci-C ⁇ -alkyl, heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl, heterocyclylcarbonyl-Ci-C ö -alkyl, N- (C ⁇ -C 6 -alkyl) -l-, -aminocyyl : 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, ie, for example 5-link rings such as: Tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydrothien-2-yl, tetrahydrothien-3-yl, tetrahydropyrrol-2-yl, tetrahydropyrrol-3-yl, 2, 3-dihydrofuran-2-yl,
  • 6-link rings such as:
  • a bicyclic ring system can be formed with a fused-on phenyl ring or with a C 3 -C 6 carbocycle or with a further 5- to 6-membered heterocycle.
  • N-linked heterocyclyl a saturated, partially saturated or unsaturated 5- or 6-membered N-linked heterocyclic ring, the at least one nitrogen and optionally one to three identical or different hetero atoms, selected from the following group: oxygen, sulfur or nitrogen contains, e.g.
  • N-linked 5-membered rings such as:
  • 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-l, 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-d
  • Tricyclic pyrazolone derivatives of the formula III are preferred
  • Tricyclic pyrazolone derivatives of the formula IV are also preferred
  • the variables preferably have the following meanings, in each case individually or in combination:
  • R 1 is hydrogen, C ⁇ -C 6 -alkyl, -C-C 6 -haloalkyl, Ci-C ⁇ -alkoxy, C ⁇ -C 6 -alkylthio, C ⁇ -C 6 -alkylsulfonyl, halogen, cyano or nitro;
  • R 2 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkyl, Ci-C ß -haloalkoxy, optionally with C 1 -C 3 -alkyl, halogen, cyano, nitro or Ci -C 3 -alkyl-sulfonyl-substituted phenyl or phenylsulfonyl optionally substituted with -C-C 3 -alkyl, halogen, cyano or nitro;
  • R 3, R 4 are hydrogen, C 6 -alkyl, C 6 alkoxy, Ci-C6 alkyl - thio, C ⁇ -C 6 alkylsulfonyl, C 2 -C 6 alkoxyalkyl, C ⁇ -C 6 - Alkoxycarbonyl, C 1 -C 6 -alkylcarbonyl, halogen, optionally substituted with C 1 -
  • R5 is hydrogen
  • R6 is hydrogen, C ⁇ -C 3 alkyl or halogen
  • R 11 is hydrogen or C 1 -C 4 alkyl, such as methyl, ethyl or propyl or 1-methylethyl; preferably methyl, ethyl, propyl or 1-methylethyl; particularly preferably methyl or ethyl;
  • Ri is hydrogen or C 1 -C 4 alkyl, such as methyl, ethyl or propyl; preferably hydrogen or methyl; particularly preferably hydrogen;
  • C ⁇ -C 6 alkyl preferably C ⁇ -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C ⁇ alkynyl, C ⁇ -C 6 alkylcarbonyl, C ⁇ -C 6 -alkoxycarbonyl, C -C_ alkyl aminocarbonyl or N, N-di (Ci-C ⁇ alkyl) aminocarbonyl, WO at the alkyl or alkoxy radicals to be partially or fully halogenated and / or may carry one to three of the following groups: cyano, C -alkoxy, -alkylthio C or Ci-C 4 alkoxycarbonyl;
  • Phenylcarbonyl, phenoxycarbonyl, heterocyclyl, heterocyclyl -C-C 6 alkyl, heterocyclylcarbonyl -Ci-C ß -alkyl, heterocyclylcarbonyl or heterocyclyloxycarbonyl, where the phenyl or heterocyclyl radical of the 10 last-mentioned substituents can be partially or completely or halogenated may carry one to three of the following radicals: nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C ⁇ -C 4 -alkoxy or C 1 -C 4 -haloalkoxy;
  • Di- (-C 6 -alkyl) amino where the alkyl, cycloalkyl or alkoxy radicals mentioned can be partially or completely halogenated and / or can carry one to three of the following radicals: cyano, C 1 -C 4 - Alkoxycarbonyl, C 1 -C 4 -alkylaminocarbonyl, di- (C 1 -C 4 -alkyl) aminocarbonyl or C 3 -C ⁇ -cycloalkyl;
  • R 1 is methyl, ethyl, halogen, methoxy, methylthio, methylsulfonyl, nitro, cyano;
  • R 2 is methyl, ethyl, optionally with halogen, cyano,
  • R 3 , R 4 are hydrogen, Ci-C ⁇ -alkyl, Ci-C ⁇ -alkylcarbonyl, phenyl optionally substituted by halogen, cyano, nitro;
  • R 5 is hydrogen
  • R 6 is hydrogen, methyl, chlorine
  • Ro halogen OR- 3 , SR 13 , S0 2 R 14 , OS0 2 R 4 , NRi 7 R 8 , ONRiRi or N-linked heterocyclyl, which can be partially or completely halogenated and / or can carry one to three of the following radicals : Nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or Ci -C 4 haloalkoxy;
  • R 2 is hydrogen or C 1 -C 4 alkyl
  • Residual definitions R i to R i8 , X, 1 and n not only have a special meaning for the compounds according to the invention, not only in combination with one another, but also in isolation.
  • R i -R i8 , X, 1 and n have the meaning given above and h 1 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 tri - fluoroacetate etc.
  • halogen for example bromine or chlorine
  • hetaryl for example imidazolyl or pyridyl
  • carboxylate for example acetate or tri - fluoroacetate etc.
  • the activated benzoic acid Va can be used directly, as in the case of the benzoyl halides, or generated in situ, e.g. with dicyclohexylcarbodiimide, triphenylphosphine / azodicarboxylic acid ester, 2-pyridine disulfide / triphenylphosphine, carbonyldiimidazole etc.
  • auxiliary base it may be advantageous to carry out the acylation reaction in the presence of a base.
  • the reactants and the auxiliary base are expediently used in equimolar amounts.
  • a slight excess of the auxiliary base e.g. Under certain circumstances, 1.2 to 1.5 molar equivalents, based on Va or Vb, can be advantageous.
  • Tertiary alkyl amines, pyridine or alkali metal carbonates are suitable as auxiliary bases.
  • a solvent e.g. chlorinated hydrocarbons such as methylene chloride or 1, 2-dichloroethane, aromatic hydrocarbons such as toluene, xylene or chlorobenzene, ethers such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran or dioxane, polar aprotic solvents such as acetonitrile, dimethylformamide or dimethyl sulfoxide or ester such as ethyl acetate or mixtures thereof.
  • chlorinated hydrocarbons such as methylene chloride or 1, 2-dichloroethane
  • aromatic hydrocarbons such as toluene, xylene or chlorobenzene
  • ethers such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran
  • benzoyl halides are used as the activated carboxylic acid component, it may be expedient to cool the reaction mixture to 0-10 ° C. when this reactant is added. The mixture is then stirred at 20-100 ° C., preferably at 25-50 ° C., until the reaction is complete. The processing takes place in the usual way, e.g. the reaction mixture is poured onto water and the product of value is extracted. Methylene chloride, diethyl ether and ethyl acetate are particularly suitable as solvents for this. After drying the organic phase and removing the solvent, the crude ester can be used for the rearrangement without further purification.
  • the rearrangement of the esters to the compounds of the formula I is advantageously carried out at from 20 to 100 ° C. in a solvent and in the presence of a base and, if appropriate, using a cyano compound as a catalyst.
  • a solvent for example, acetonitrile, methylene chloride, 1, 2-dichloroethane, dioxane, ethyl acetate, toluene or mixtures thereof can be used as solvents.
  • Preferred solvents are acetonitrile and dioxane. 5
  • 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 10 ester.
  • Triethylamine or alkali carbonate are preferably used, preferably in a double equimolar ratio with respect to the ester.
  • Suitable cyano compounds are inorganic cyanides, such as sodium cyanide or potassium cyanide, and organic cyano compounds, such as acetone cyanohydrin or trimethylsilyl cyanide. They are used in an amount of 1 to 50 mole percent, based on the ester. Preferably acetone cyanohydrin or trimethylsilyl cyanide, e.g. in an amount of 5 to 15, preferably about 10 mol percent, based on the ester.
  • reaction mixture is e.g. with dilute mineral acid
  • organic solvent e.g. Extracted methylene chloride or ethyl acetate.
  • the organic extract can be mixed with 5-10% alkali carbonate solution, e.g. Sodium carbonate or potassium carbonate solution can be extracted.
  • alkali carbonate solution e.g. Sodium carbonate or potassium carbonate solution can be extracted.
  • Suitable halogenating agents are, for example, phosgene, diphosgene, triphosgene, thionyl chloride, oxalyl chloride, phosphorus oxychloride, phosphorus pentachloride, mesyl chloride, chloromethylene-N, N-dimethylammonium chloride, oxalyl bromide, phosphorus oxybromide etc.
  • L 2 stands for a nucleophilically displaceable leaving group, such as halogen, for. B. chlorine or bromine, hetaryl, e.g. B. imidazolyl, carboxylate, e.g. B. acetate, or sulfonate, e.g. B. mesylate or triflate etc.
  • halogen for. B. chlorine or bromine
  • hetaryl e.g. B. imidazolyl
  • carboxylate e.g. B. acetate
  • sulfonate e.g. B. mesylate or triflate etc.
  • the compounds of formula A ⁇ , Aß, A ⁇ or A ⁇ can be used directly, such as. B. in the case of carboxylic acid halides or generated in situ, for. B. activated carboxylic acids (with carboxylic acid and dicyclohexylcarbodiimide etc.).
  • Suitable oxidizing agents are m-chloroperbenzoic acid, peroxyacetic acid, trifluoroperoxyacetic acid, hydrogen peroxide, if appropriate in the presence of a catalyst such as tungstate.
  • the compounds of the formula V are prepared by oxidation of the compounds of the formula XIII using oxidizing agents:
  • Suitable oxidizing agents are, for example, m-chloroperbenzoic acid, peroxyacetic acid or hydrogen peroxide, if appropriate in the presence of a catalyst such as tungsten.
  • Compounds of the formula Xllla are prepared by dipolar cycloaddition of compounds of the formula XIV in the presence of an oxidizing agent (see, for example, Kim, JN et.al. Synth. Commun. 1990, 20, 1373; Hassner, A. et. Al. Synthesis 1989, 57; Kellabennani, AE et al. Tetrahedron 1995, 51, 10923),
  • T is C1-C 4 alkoxy and the remaining substituents have the meanings described above.
  • oxidizing agents come e.g. Chloramine T or sodium hypochlorite are used.
  • the oximes XIV are prepared using generally known methods from the aldehydes XVI (see March, J. Advanced Organic Chemistry, 4th Ed., Wiley and Sons 1992, pp. 906 ff.).
  • the hydrazone XV is represented by generally known methods from the aldehydes XVI (see March, J. Advanced Organic Chemistry, 4th Ed., Wiley, 1992, pp. 904 ff.).
  • Compounds of the formula XVI are prepared by nucleophilic aromatic substitution of compounds of the formula XVII with substituted allyl thiols in polar solvents in the presence of bases.
  • Tertiary amines such as triethylamine or pyridine or alkali metal carbonates such as lithium carbonate or sodium carbonate can be used as the base.
  • Methanol, ethanol, dimethylformamide or N-methyl-pyrrolidone are suitable as solvents.
  • aldehydes of the formula XVII are known from, for example, WO 98/31681.
  • step d) The acid from step d) (4.4 g, 16.3 mmol) was dissolved in 30 ml of glacial acetic acid and a spatula tip of sodium tungstate was added. Thereafter, perhydrol (4.16 g, 36.7 mmol) was added dropwise at 50 ° C. and the mixture was stirred at 50 ° C. for a further 4 h. The mixture was stirred into ice water and extracted with ethyl acetate. The organic phase was washed with water, dried over sodium sulfate and concentrated.
  • the compounds I and their agriculturally useful salts are suitable - both as isomer mixtures and in the form of the pure isomers - as herbicides.
  • the herbicidal compositions containing I control vegetation very well on non-cultivated areas, particularly when high amounts are applied. In crops such as wheat, rice, corn, soybeans and cotton, they act against weeds and grass weeds without significantly damaging the crop plants. This effect occurs especially at low application rates.
  • the compounds I or compositions containing them can also be used in a further number of crop plants for eliminating undesired plants.
  • the following crops are considered, for example:
  • the compounds I can also be used in crops which are tolerant to the action of herbicides by breeding, including genetic engineering methods.
  • the herbicidal compositions or the active compounds can be applied pre- or post-emergence. If the active ingredients are less compatible with certain crop plants, application techniques can be used in which the herbicidal compositions are sprayed with the aid of sprayers in such a way that the leaves of the sensitive crop plants are not hit, if possible, while the active ingredients are applied to the leaves underneath growing unwanted plants or the uncovered floor area (post-directed, lay-by).
  • the compounds I or the herbicidal compositions comprising them can be sprayed or atomized, for example in the form of directly sprayable aqueous solutions, powders, suspensions, including high-strength aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, sprays or granules , Dusting, scattering or pouring.
  • the application forms depend on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
  • Mineral oil fractions from medium to high boiling point such as kerosene or diesel oil, also coal tar oils as well as oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, alkylated benzenes or their derivatives, alcohols such as methanol, ethanol, propanol, butanol, cyclohexanol, ketones such as cyclohexanone or strongly polar solvents, e.g. B. amines such as N-methylpyrrolidone or water.
  • Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water.
  • the tricyclic pyrazolone derivatives as such or dissolved in an oil or solvent, can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers.
  • concentrates consisting of an active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil, which are suitable for dilution with water.
  • the surface-active substances are the alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic acids, for example lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa- , Hepta- and octadecanols 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 or nonylphenyl glycolphenyl, alkylphen -
  • Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
  • Granules e.g. Coated, impregnated and homogeneous granules can be produced by binding the active ingredients to solid carriers.
  • Solid carriers are mineral soils such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, Urea and vegetable products such as flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
  • the concentrations of the active ingredients I in the ready-to-use preparations can be varied over a wide range.
  • the formulations generally contain 0.001 to 98% by weight, preferably 0.01 to 95% by weight, of at least one active ingredient.
  • the active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).
  • the compounds I according to the invention can be formulated, for example, as follows:
  • Mixture in 20,000 parts by weight of water contains a spray mixture which contains 0.1% by weight of the active ingredient.
  • V 3 parts by weight of active ingredient No. 23.2 are mixed with 97 parts by weight of finely divided kaolin. In this way a dust is obtained which contains 3% by weight of the active ingredient.
  • VI 20 parts by weight of active ingredient No. 23.2 are intimately mixed with 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.
  • the active compound application rates are 0.001 to 3.0, preferably 0.01 to 1.0 kg / ha of active substance (see p.)
  • Plastic pots with loamy sand with about 3.0% humus as substrate served as culture vessels.
  • the seeds of the test plants were sown separately according to species.
  • the active ingredients suspended or emulsified in water were applied directly after sowing using finely distributing nozzles.
  • the containers were lightly sprinkled to promote germination and growth, and then covered with clear plastic covers until the plants had grown. This cover causes the test plants to germinate evenly, unless this was affected by the active ingredients.
  • test plants were first grown to a height of 3 to 15 cm, depending on the growth habit, and then treated with the active ingredients suspended or emulsified in water.
  • the test plants were either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days before the treatment.
  • the application rate for post-emergence treatment was 0.5 or 0.25 kg / ha a. S.
  • the plants were kept at temperatures of 10 - 25 ° C or 20 - 35 ° C depending on the species.
  • the trial period lasted 2 to 4 weeks. During this time, the plants were cared for and their response to each treatment was evaluated.
  • Evaluation was carried out on a scale from 0 to 100. 100 means no emergence of the plants or complete destruction of at least the aerial parts and 0 means no damage or normal growth.
  • the plants used in the greenhouse experiments are composed of the following types:
  • the compound 23.2 showed a very good effect against the undesirable plants of white goose foot, more curved backwards Foxtail, flea knotweed, black nightshade and honorary prize types.

Abstract

The invention relates to tricyclic pyrazolone derivatives of the formula (I) in which the variables have the following meaning: R1 is hydrogen, C¿1?-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, halogen, cyano or nitro; X is O or NR?2; R2¿ is hydrogen, C¿1?-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkyl, C1-C6-haloalkoxy, phenyl possibly substituted with C1-C3-alkyl, halogen, cyano, nitro or C1-C3-alkylsulfonyl, phenylsulfonyl possibly substituted with C1-C3-alkyl, halogen, cyano, nitro; R?3, R4¿ are hydrogen, C¿1?-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, NR?7R8, C¿2-C6-alkoxyalkyl, C1-C6-alkoxycarbonyl, C1-C6-alkylcarbonyl, halogen, cyano, nitro, phenyl possibly substituted with C1-C3-alkyl, halogen, cyano or nitro; R5 is hydrogen or C¿1?-C4-alkyl; R?6¿ is hydrogen, C¿1?-C6-alkyl or halogen; R?7¿ is hydrogen or C¿1?-C6-alkyl; R?8 is C¿1-C6-alkyl or C1-C6-alkoxy; l is 0, 1 or 2; n is 1 or 2; R9 is a rest of the formulas (IIa) or (IIb), in which the variables have the meanings stated in claim I. The invention also relates to methods for the preparation of said tricyclic pyrazolone derivatives, preparations containing same and the use of said derivatives or of preparations containing same as herbicides.

Description

Tricyclische PyrazolonderivateTricyclic pyrazolone derivatives
Beschreibungdescription
Die vorliegende Erfindung betrifft neue tricyclische Pyrazolonderivate mit herbizider Wirkung, Verfahren zur Herstellung der tricyclischen Pyrazolonderivate, Mittel welche diese enthalten sowie die Verwendung dieser Derivate oder sie enthaltender Mittel zur Unkrautbekämpfung .The present invention relates to new tricyclic pyrazolone derivatives with herbicidal activity, processes for the preparation of the tricyclic pyrazolone derivatives, agents which contain them and the use of these derivatives or agents comprising weeds for combating weeds.
Aus der Literatur sind herbizidwirksame tricyclische Pyrazolonderivate bekannt, beispielsweise aus WO 97/19087.Herbicidal tricyclic pyrazolone derivatives are known from the literature, for example from WO 97/19087.
Die herbiziden Eigenschaften der bekannten Verbindungen sowie die Verträglichkeit gegenüber Kulturpflanzen können jedoch nur bedingt befriedigen.However, the herbicidal properties of the known compounds and the compatibility with crop plants can only satisfy to a limited extent.
Die Aufgabe bestand darin neue tricyclische Pyrazolonderivate mit verbesserten Eigenschaften zu finden.The task was to find new tricyclic pyrazolone derivatives with improved properties.
Es wurden nun neue tricyclische Pyrazolonderivate der Formel I gefundenNew tricyclic pyrazolone derivatives of the formula I have now been found
Figure imgf000003_0001
Figure imgf000003_0001
wobei die Variablen folgende Bedeutung haben:where the variables have the following meaning:
R1 Wasserstoff, C*ι-C6-Alkyl, Cι-C6-Haloalkyl,R 1 is hydrogen, C * ι-C 6 -alkyl, C 6 haloalkyl,
Cι-C6-Alkoxy, Cι-C6-Haloalkoxy, Cι-C6-Alkylthio, Cι-C6-Haloalkylthio, Cι-C6-Alkylsulfinyl, C-χ-C6-Halo- alkylsulfinyl, Ci-Ce-Alkylsulfonyl, Ci-Cδ-Haloalkyl- sulfonyl, Halogen, Cyano- oder Nitro;C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulfinyl, C-χ-C 6 -haloalkylsulfinyl, Ci-Ce- Alkylsulfonyl, Ci-C δ -haloalkylsulfonyl, halogen, cyano- or nitro;
X 0 oder NR2;X 0 or NR 2 ;
R2 Wasserstoff, Cι-C6-Alkyl, Cι-C6-Alkoxy, Cι-C6-Halo- alkyl, Cι-C6-Haloalkoxy, gegebenenfalls mitR 2 is hydrogen, -CC 6 -alkyl, -C-C 6 -alkoxy, -C-C 6 -haloalkyl, -C-C 6 -haloalkoxy, optionally with
Cι-C3-Alkyl, Halogen, Cyano, Nitro oder Cχ-C3-Alkyl- sulfonyl substituiertes Phenyl oder gegebenenfalls mit Cχ-C3-Alkyl, Halogen, Cyano oder Nitro substituiertes Phenylsulfonyl;-C-C 3 alkyl, halogen, cyano, nitro or Cχ-C 3 alkyl sulfonyl substituted phenyl or optionally phenylsulfonyl substituted with Cχ-C 3 alkyl, halogen, cyano or nitro;
R3, R4 Wasserstoff, Cι-C6-Alkyl, Cι-C6-Haloalkyl, Cι-C6-Alkoxy, Cι-C6-Haloalkoxy, Cι-C6-Alkylthio,R 3 , R 4 are hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio,
Cι-C6-Haloalkylthio, Cι-C6-Alkylsulfinyl, Cι-C6-Halo- alkylsulfinyl, Cι-C6-Alkylsulfonyl, Cι-C6-Haloalkyl- sulfonyl, NR7R8, C2 -C6 -Alkoxyalkyl, Cι-C6-Alkoxy- carbonyl, Cι-C6-Alkyicarbonyl, Halogen, Cyano, Nitro, gegebenenfalls mit Cχ-C3 -Alkyl, Halogen, Cyano oder Cι-C6 haloalkylthio, Cι-C 6 alkylsulfinyl, Cι-C 6 -Halo- alkylsulfinyl, Cι-C 6 alkylsulfonyl, Cι-C 6 haloalkyl sulfonyl, NR 7 R 8, C 2 -C 6 - Alkoxyalkyl, -CC 6 alkoxy carbonyl, -C 6 -alkyicarbonyl, halogen, cyano, nitro, optionally with Cχ-C 3 alkyl, halogen, cyano or
Nitro substituiertes Phenyl;Nitro substituted phenyl;
R5 Wasserstoff oder C1-C4 -Alkyl;R 5 is hydrogen or C 1 -C 4 alkyl;
R6 Wasserstoff, Cι-C6-Alkyl oder Halogen;R 6 is hydrogen, -CC 6 alkyl or halogen;
R7 Wasserstoff oder i-C6-Alkyl;R 7 is hydrogen or iC 6 alkyl;
R8 Ci-C6 -Alkyl oder Cι-C6-Alkoxy;R 8 Ci-C 6 alkyl or -CC 6 alkoxy;
1 0, 1 oder 2;1 0, 1 or 2;
n 1 oder 2;n 1 or 2;
R9 ein Rest Ha oder Ilb,R 9 is a residue Ha or Ilb,
Figure imgf000004_0001
wobei die Variablen folgende Bedeutung haben:
Figure imgf000004_0001
where the variables have the following meaning:
Ri° Hydroxy, Mercapto , Halogen, OR13 , SR13 , SOR14 , S02R14 ,Ri ° Hydroxy, Mercapto, Halogen, OR 13 , SR 13 , SOR 14 , S0 2 R 14 ,
OS02R14 , P (0) Rl5R16 , OP (0) R15R16 , P (S) R15R16 , OP ( S) R15R16 , NR17R18 , ONR1 R14 oder N- gebundenes Heterocyclyl, das partiell oder vollständig haloge- niert sein kann und/oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, C1-C4-Alkyl, Cι-C4-Halogenalkyl, Cι-C4-Alkoxy oder Cι-C4-Halogenal- koxy; Wasserstoff, Cι-C6-Alkyl, Cι-C6-Halogenalkyl,OS0 2 R 14, P (0) (0) R 15 R 16, P (S) R 15 R 16, OP (S) R 15 R 16, NR 17 R 18 R l5 R 16, OP, ONR 1 R 14 or N-bonded heterocyclyl which may be partially or fully halogenated defined and / or may carry one to three of the following radicals: nitro, cyano, C 1 -C 4 -alkyl, C 4 haloalkyl, Cι-C 4 -Alkoxy or -CC 4 haloalkoxy; Are hydrogen, C 6 -alkyl, C 6 haloalkyl,
Ci-Cδ-Alkoxy oder Ci-Cδ-Halogenalkoxy;Ci-C δ alkoxy or Ci-C δ haloalkoxy;
Wasserstoff, Halogen, Ci-Cβ-Alkyl, Cι-C6-Halogenal- kyl, Ci-Cδ-Alkoxy, Cι*-C6-Halogenalkoxy, Ci-Cδ-Alkyl- thio oder Ci-Cß-Halogenalkylthio;Hydrogen, halogen, Ci-Cβ-alkyl, Cι-C 6 -Halogenal- -alkyl, Ci-C δ alkoxy, Cι * -C 6 haloalkoxy, Ci-C δ -alkylthio or C ß haloalkylthio;
Cx-Cδ-Alkyl, C3-C6-Alkenyl, C3-C6-Halogenalkenyl,Cx-C δ alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl,
C3-C6-Alkinyl, C3-C6-Halogenalkinyl, C3-C6-Cycloalkyl, Ci-Cδ-Alkylcarbonyl, C2-C6-Alkenylcarbonyl,C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, C 3 -C 6 cycloalkyl, Ci-C δ alkylcarbonyl, C 2 -C 6 alkenylcarbonyl,
C2-C6-Alkinylcarbonyl , C3-C6-Cycloalkylcarbonyl , Ci-Cö-Alkoxycarbonyl , C3-C6-Alkenyloxycarbonyl , C3-C6-Alkinyloxycarbonyl , Ci -C6 -Alkylthiocarbonyl , Ci-Cö-Alkylaminocarbonyl , C3-C6-Alkenylaminocarbonyl , C3-C6-Alkinylaminocarbonyl, N,N-Di- (Ci-Cδ *- alkyl) -aminocarbonyl, N- (C3-C6-Alkenyl) -N- (Cι-C6- alkyD-aminocarbonyl, N- (C3-C6-Alkinyl) -N- (Ci-Cε- alkyl) -aminocarbonyl, N- (Cι-C6 *-Alkoxy) -N- (Ci-Cö- alkyl) -aminocarbonyl, N- (C3-C6-Alkenyl) -N- (Ci-Cβ- alkoxy) -aminocarbonyl , N- (C3-C6-Alkinyl ) -N- (Ci-Cβ- alkoxy) -aminocarbonyl, Di- (Ci-Cβ-alkyl) -aminothio- carbonyl oder Cι-C6-Alkoxyimino-Cι-C6-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, C1-C4-Alkoxy, Cι-C4-Alkylthio, Di- (Cι~C4-alkyl) -amino, Cι-C4-Alkylcarbonyl, Cι-C4-Alkoxycarbonyl , Cι-C4-Alkoxy-Cι-C4-alkoxy- carbonyl, Hydroxycarbonyl, Cι-C4-Alkylaminocarbonyl, Di- (Cι-C4-alkyl) -aminocarbonyl, Aminocarbonyl,C 2 -C 6 alkynylcarbonyl, C 3 -C 6 cycloalkylcarbonyl, Ci-Cö-alkoxycarbonyl, C 3 -C 6 -alkenyloxycarbonyl, C 3 -C 6 -alkynyloxycarbonyl, Ci- 6- alkylthiocarbonyl, Ci-Cö-alkylaminocarbonyl , C 3 -C 6 alkenylaminocarbonyl, C 3 -C 6 alkynylaminocarbonyl, N, N-di- (Ci-C δ * - alkyl) -aminocarbonyl, N- (C 3 -C 6 alkenyl) -N- ( -C-C 6 - alkyD-aminocarbonyl, N- (C 3 -C 6 -alkynyl) -N- (Ci-Cε-alkyl) -aminocarbonyl, N- (Cι-C 6 * -alkoxy) -N- (Ci Cö-alkyl) -aminocarbonyl, N- (C 3 -C 6 -alkenyl) -N- (Ci-Cβ-alkoxy) -aminocarbonyl, N- (C 3 -C 6 -alkynyl) -N- (Ci-Cβ- alkoxy) -aminocarbonyl, di- (Ci-Cβ-alkyl) -aminothio-carbonyl or -CC 6 alkoxyimino -CC 6 -alkyl, where the alkyl, cycloalkyl and alkoxy radicals mentioned can be partially or completely halogenated and / or may carry one to three of the following groups: cyano, C 1 -C 4 -alkoxy, C 4 alkylthio, di (Cι ~ C4 alkyl) amino, Cι-C 4 alkylcarbonyl, Cι- C 4 alkoxycarbonyl, -CC 4 alkoxy -C-C 4 -alkoxy- carbonyl, hydroxycarbonyl, -C-C 4 -alkylaminocarbonyl, di- (-C-C 4 -alkyl) -aminocarbonyl, aminocarbonyl,
Cι-C -Alkylcarbonyloxy oder C3-C6-Cycloalkyl;-CC alkylcarbonyloxy or C 3 -C 6 cycloalkyl;
Phenyl, Phenyl-Ci-Cδ-alkyl, Phenylcarbo- nyl-Ci-Cβ-alkyl, Phenylcarbonyl , Phenoxycarbonyl , Phenyloxythiocarbonyl , Phenylaminocarbonyl,Phenyl, phenyl-Ci-C δ -alkyl, phenylcarbonyl-Ci-Cβ-alkyl, phenylcarbonyl, phenoxycarbonyl, phenyloxythiocarbonyl, phenylaminocarbonyl,
N- (Ci-Cβ-Alkyl) -N- (phenyl) -aminocarbonyl, Phenyl -C2-C6-alkenylcarbonyl , Heterocyclyl , Heterocy- clyl -Ci - Cζ -alkyl , Heterocyclylcarbonyl -Ci -Cß - alkyl , Heterocyclylcarbonyl, Heterocyclyloxycarbonyl, Hete- rocyclyloxythiocarbonyl , Heterocyclylaminocarbonyl,N- (Ci-Cβ-alkyl) -N- (phenyl) aminocarbonyl, phenyl -C 2 -C 6 alkenylcarbonyl, heterocyclyl, heterocyclyl -Ci - Cζ alkyl, heterocyclylcarbonyl -Ci -C ß - alkyl, heterocyclylcarbonyl , Heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl, heterocyclylaminocarbonyl,
N- (Ci-Cβ-Alkyl) -N- (heterocyclyl) -aminocarbonyl, oder Heterocyclyl-C-C6-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 tra- gen kann: Nitro, Cyano, Cι-C4-Alkyl, Cχ-C4-Halogen- alkyl, C1-C4-Alkoxy oder Cι-C-Halogenalkoxy;N- (Ci-Cβ-alkyl) -N- (heterocyclyl) aminocarbonyl, or heterocyclyl-CC 6 -alkenylcarbonyl, where the phenyl and the heterocyclyl radical of the 18 latter substituents can be partially or completely halogenated and / or one to three of the following residues can gen: nitro, cyano, C 4 alkyl, Cχ-C4 halo-alkyl, C 1 -C 4 alkoxy or Cι-C -haloalkoxy;
i4 Cι-C6-Alkyl, C3-C6-Alkenyl, C3-C6-Alkinyl oder C3-C6-Cycloalkyl, wobei die vier genannten Reste partiell oder vollständig halogeniert sein können und/ oder eine bis drei der folgenden Gruppen tragen können: Cyano, Cι-C4-Alkoxy, C1-C4 -Halogenalkoxy, Cι-C4-Alkylthio, Cι-C4-Halogenalkylthio, Cι-C4-Alkyl- carbonyl, C1-C4-Alkoxycarbonyl oder Cι-C4-Halogenal- koxycarbonyl;i4 -CC 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl or C 3 -C 6 cycloalkyl, where the four radicals mentioned can be partially or completely halogenated and / or one to three of the can carry the following groups: cyano, C 4 alkoxy, C 1 -C 4 haloalkoxy, Cι-C 4 alkylthio, Cι-C4-haloalkylthio, Cι-C 4 alkyl carbonyl, C 1 -C 4 -Alkoxycarbonyl or -CC 4 -haloalkoxycarbonyl;
Phenyl, Phenyl-Cι-C6-alkyl, Heterocyclyl oder Hetero- cyclyl-Ci-Cg-alkyl, wobei der Phenyl- und der Hetero- cyclyl-Rest der letztgenannten Substituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, C1-C -Alkyl, Cι-C4-Halogenalkyl, Cι-C4-Alkoxy, C1-C4-Halogenalkoxy oder C1-C4 -Alkoxycarbonyl;Phenyl, phenyl -CC 6 alkyl, heterocyclyl or heterocyclic-Ci-Cg-alkyl, where the phenyl and the heterocyclic radical of the latter substituents can be partially or completely halogenated and / or one to three of the may carry the following radicals: nitro, cyano, C 1 -C -alkyl, C 4 haloalkyl, Cι-C 4 alkoxy, C 1 -C 4 -haloalkoxy or C 1 -C 4 alkoxycarbonyl;
Ris. R16 Wasserstoff, Hydroxy, C^-CÖ -Alkyl, Cι-C6 -Alkoxy, Ci-Cδ-Alkylthio, Phenyl, Phenyl-C1-C4-alkyl oder Phenoxy, wobei die drei letztgenannten Substituenten partiell oder vollständig halogeniert sein können und/oder einen bis drei der folgenden Reste tragen können: Nitro, Cyano, Cι-C4-Alkyl, Ci-C4-Halogen- alkyl, C1-C4 -Alkoxy, C1-C4 -Halogenalkoxy oder Ci -C4 -Alkoxycarbonyl ;Ris. R16 is hydrogen, hydroxy, C ^ -C east -alkyl, C 6 alkoxy, Ci-C δ alkylthio, phenyl, phenyl-C 1 -C 4 alkyl or phenoxy, where the three last-mentioned substituents partially or fully halogenated can be and / or may carry one to three of the following radicals: nitro, cyano, C 4 alkyl, halo-Ci-C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 -haloalkoxy or Ci -C 4 alkoxycarbonyl;
R17 Wasserstoff, Cι-C6-Alkyl, C3-C6-Alkenyl,R 17 is hydrogen, -CC 6 alkyl, C 3 -C 6 alkenyl,
C3-C6-Halogenalkenyl, C3-C6-Alkinyl, C3-C6"Halogen- alkinyl, C3-C6-Cycloalkyl, C3.-C6-Alkylcarbonyl, Hydroxy, Cι-C6 -Alkoxy, C3-C6-Alkenyloxy, C3-C6-Alkinyloxy, Amino, Cι-C6-Alkylamino, Di- (C-i-Cβ-alkyl) -amino oder Ci-Cö-Alkylcarbonylamino, wobei die genannten Alkyl-, Cycloalkyl- und Alkoxy- reste partiell oder vollständig halogeniert sein können und/oder einen bis drei Reste der folgenden Gruppe tragen können: Cyano, C1-C4 -Alkoxycarbonyl, Cι-C4-Alkylaminocarbonyl, Di- (C3.-C4- alkyl) -aminocarbonyl oder C3 -C$ -Cycloalkyl ;C 3 -C 6 haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 "haloalkynyl, C 3 -C 6 cycloalkyl, C 3. -C 6 alkylcarbonyl, hydroxy, -C-C 6 - alkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy, amino, Cι-C 6 -alkylamino, di- (Ci-Cβ alkyl) amino or C ö alkylcarbonylamino wherein the alkyl mentioned -, 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 alkoxycarbonyl, C 1 -C 4 alkylaminocarbonyl, di (C 3. -C 4 alkyl) aminocarbonyl or C 3 -C $ cycloalkyl;
Phenyl, Phenyl -C1-C4-alkyl, Phenylcarbonyl, Heterocyclyl, Heterocyclyl -C1-C4-alkyl oder Heterocyclyl - carbonyl, wobei der Phenyl- oder Heterocyclyl -Rest der sechs letztgenannten Substituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, C1-C4 -Alkyl, Cι-C -Halogenalkyl, C3.-C4 -Alkoxy oder Ci -C4 -Halogenalkoxy;Phenyl, phenyl -C 1 -C4-alkyl, phenylcarbonyl, heterocyclyl, heterocyclyl -C1-C4-alkyl or heterocyclyl - carbonyl, where the phenyl or heterocyclyl radical of the latter six substituents can be partially or completely halogenated and / or one to can carry three of the following radicals: nitro, cyano, C 1 -C 4 -alkyl, C haloalkyl, C 3 -C 4 alkoxy or Ci-C4 haloalkoxy;
sowie landwirtschaftlich brauchbare Salze der Verbindungen I.as well as agriculturally useful salts of the compounds I.
Ferner wurden herbizide Mittel gefunden, die die Verbindungen I enthalten und eine sehr gute herbizide Wirkung besitzen. Außerdem wurden Verfahren zur Herstellung dieser Mittel und Verfahren zur Bekämpfung von unerwünschtem Pflanzenwuchs mit den Verbindungen I gefunden.Furthermore, herbicidal compositions have been found which contain the compounds I and have a very good herbicidal action. In addition, processes for the preparation of these compositions and processes for controlling unwanted vegetation using the compounds I have been found.
Die Verbindungen der Formel I können je nach Substitutionsmuster ein oder mehrere Chiralitätszentren enthalten und liegen dann als Enantiomeren oder Diastereomerengemische vor. Gegenstand der 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 centers of chirality and are then present as enantiomers or mixtures of diastereomers. The invention relates both to the pure enantiomers or diastereomers and to their mixtures.
Die Verbindungen der Formel I können auch in Form ihrer landwirt- schaftlich 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 beeinträch- tigen.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-C-alkyl, Cι-C4-Alkoxy-Cι-C4-alkyl, Hydro- xy-Cι-C4-alkoxy-Cι-C4-alkyl, Phenyl oder Benzyl ersetzt sein können, vorzugsweise Ammonium, Dimethylammonium, Diisopropyl- ammonium, Tetramethylammonium, Tetrabutylammonium, 2- (2 -Hydroxy- eth-1-oxy) eth-1-ylammonium, Di (2 -hydroxyeth-1-yl) ammonium, Tri- methylbenzylammonium, des weiteren Phosphoniumionen, Sulfonium- ionen, vorzugsweise Tri (Cι-C4-alkyl) sulfonium und Sulfoxonium- ionen, 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- be hydroxy-Cι-C alkyl, Cι-C4-alkoxy-Cι-C4-alkyl, hydroxy-Cι-C4-alkoxy-Cι-C replaced 4 alkyl, phenyl or benzyl C 4 alkyl can, preferably ammonium, dimethylammonium, diisopropylammonium, tetramethylammonium, tetrabutylammonium, 2- (2-hydroxy-eth-1-oxy) eth-1-ylammonium, di (2-hydroxyeth-1-yl) ammonium, trimethylbenzylammonium, 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. Im Falle von R10 = Hydroxy oder Mercapto {Y = O, S} steht Ha auch stellvertretend für die tautomeren Formen Ha' und Ha' ' ,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. In the case of R 10 = hydroxy or mercapto {Y = O, S}, Ha also represents the tautomeric forms Ha 'and Ha'',
Figure imgf000008_0001
Figure imgf000008_0001
Ha Ha' na' 'Ha Ha 'na'
bzw. Ilb auch stellvertretend für die tautomeren Formen Ilb' und Ilb' ' .and Ilb also represent the tautomeric forms Ilb 'and Ilb' '.
Figure imgf000008_0002
Figure imgf000008_0002
Ilb Ilb' Ilb' 'Ilb Ilb 'Ilb' '
Die für die Substituenten R1-R18 oder als Reste an Phenyl-, Heterocyclyl- und N-Heterocyclyl-Resten genannten organischen Molekülteile stellen Sammelbegriffe für individuelle Aufzählungen der einzelnen Gruppenmitglieder dar. Sämtliche Kohlenwasserstoff - ketten, also alle Alkyl-, Halogenalkyl-, Alkoxy-, Halogenalkoxy-, Alkylthio-, Halogenalkylthio-, Alkylsulfinyl-, Halogenalkyl - sulfinyl-, Alkylsulfonyl-, Halogenalkylsulfonyl-, N-Alkylamino- , N,N-Dialkylamino- , N-Halogenalkylarru.no- , N-Alkoxyamino- , N-Alko- xy-N-alkylamino- , Alkylcarbonyl- , Halogenalkylcarbonyl-, Alkoxycarbonyl-, Halogenalkoxycarbonyl - , Alkylthiocarbonyl- , Alkyl - carbonyloxy- , Alkylaminocarbonyl-, Dialkylaminocarbonyl-,The organic molecule parts mentioned for the substituents R 1 -R 18 or as residues on phenyl, heterocyclyl and N-heterocyclyl residues represent collective terms for individual lists of the individual group members. All hydrocarbon chains, that is to say all alkyl, haloalkyl, Alkoxy-, haloalkoxy-, alkylthio-, haloalkylthio-, alkylsulfinyl-, haloalkyl- sulfinyl-, alkylsulfonyl-, haloalkylsulfonyl-, N-alkylamino-, N, N-dialkylamino-, N-haloalkylarru.no-, N-alkoxyamino-, N-alkoxy-N-alkylamino, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, alkylthiocarbonyl, alkylcarbonyloxy, alkylaminocarbonyl, dialkylaminocarbonyl,
Dialkylaminothiocarbonyl - , Dialkoxymethyl- , Dialkylthiomethyl- , (Alkoxy) (alkylthio)methyl- , Alkoxyiminoalkyl - , Phenylalkenylcar- bonyl- , Heterocyclylalkenylcarbonyl- , N-Alkoxy-N-alkylaminocarbo- nyl-, N-Alkyl-N-phenylaminocarbonyl-, N-Alkyl-N-heterocyclylami- nocarbonyl-, Phenylalkyl-, Heterocyclylalkyl-, Phenylcarbonylal- kyl-, Heterocyclylcarbonylalkyl-, Alkoxyalkoxycarbonyl-, Alkenyl- carbonyl-, Alkenyloxycarbonyl-, Alkenylaminocarbonyl-, N-Alkenyl- N-alkylaminocarbonyl-, N-Alkenyl-N-alkoxyaminocarbonyl-, Alkinyl - carbonyl-, Alkinyloxycarbonyl-, Alkinylaminocarbonyl-, N-Alkinyl- N-alkylaminocarbonyl-, N-Alkinyl-N-alkoxyaminocarbonyl-,Dialkylaminothiocarbonyl, dialkoxymethyl, dialkylthiomethyl, (alkoxy) (alkylthio) methyl, alkoxyiminoalkyl, phenylalkenylcarbonyl, heterocyclylalkenylcarbonyl, N-alkoxy-N-alkylaminocarbonyl, N-alkyl-N-phenylaminocarbon -Alkyl-N-heterocyclylaminocarbonyl, phenylalkyl, heterocyclylalkyl, phenylcarbonylalkyl, heterocyclylcarbonylalkyl, alkoxyalkoxycarbonyl, alkenylcarbonyl, alkenyloxycarbonyl, alkenylaminocarbonyl, N-alkenylcarbonyl, N-alkylamin -N-alkoxyaminocarbonyl-, alkynyl-carbonyl-, alkynyloxycarbonyl-, alkynylaminocarbonyl-, N-alkynyl-N-alkylaminocarbonyl-, N-alkynyl-N-alkoxyaminocarbonyl-,
Alkenyl-, Alkinyl-, Halogenalkenyl-, Halogenalkinyl-, Alkenyloxy, Alkinyloxy-, Alkandiyl, Alkendiyl, Alkadiendiyl und Alkindiyl- Teile können geradkettig oder verzweigt sein. Sofern nicht anders angegeben tragen halogenierte Substituenten vorzugsweise ein bis fünf gleiche oder verschiedene Halogenatome. Die Bedeutung Halogen steht jeweils für Fluor, Chlor, Brom oder Iod.Alkenyl, alkynyl, haloalkenyl, haloalkynyl, alkenyloxy, alkynyloxy, alkanediyl, alkenediyl, alkadienediyl and alkynediyl Parts can be straight 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:
C1-C4-Alkyl, sowie die Alkylteile von Phenyl -C1-C4-alkyl und Heterocyclyl -C1-C4-alkyl: z.B. Methyl, Ethyl, Propyl, 1-Methylethyl, Butyl, 1-Methylpropyl, 2-Methylpropyl oder 1, 1-Dimethylethyl;C 1 -C 4 alkyl, and the alkyl parts of phenyl -C 1 -C 4 alkyl and heterocyclyl -C 1 -C 4 alkyl: for example methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2nd -Methylpropyl or 1, 1-dimethylethyl;
Ci-Cδ-Alkyl, sowie die Alkylteile von C*ι-C6-Alkoxyimino-Cι-C6- alkyl, N-Cι-C6-Alkoxy-N-Cι-C6-alkylamino, N(C1-C6-Alk- oxy) -N- (Cχ-C6-alkyl) -aminocarbonyl, N- (C3-C6-Al - kenyl)-N- (Ci-Cβ-alkyl) -aminocarbonyl, (C3-C6-Alki- nyl) -N- (Ci-Cδ-alkyl) -aminocarbonyl, N- (Ci-Cδ-Alkyl) -N-phenyla- minocarbonyl , N- (Ci-Cβ-Alkyl) -N-heterocyclylaminocarbonyl , Phenyl-Ci-Cg-alkyl, Heterocyclyl-Cι-C6-alkyl, Phenylcarbo- nyl-Cχ-C6-alkyl, Heterocyclylcarbonyl-Ci-Cδ-alkyl :Ci-C δ- alkyl, as well as the alkyl parts of C * ι-C 6 -alkoxyimino-Cι-C 6 - alkyl, N-Cι-C 6 -alkoxy-N-Cι-C 6 -alkylamino, N (C 1 - C 6 -alkoxy) -N- (Cχ-C 6 -alkyl) -aminocarbonyl, N- (C 3 -C 6 -alkenyl) -N- (Ci-Cβ-alkyl) -aminocarbonyl, (C 3 -C 6 -alkynyl) -N- (Ci-C δ- alkyl) -aminocarbonyl, N- (Ci-C δ- alkyl) -N-phenyla-minocarbonyl, N- (Ci-Cβ-alkyl) -N -heterocyclylaminocarbonyl, phenyl-Ci-Cg-alkyl, heterocyclyl -CC-C 6 -alkyl, phenylcarbonyl-C 6 -C 6 -alkyl, heterocyclylcarbonyl-Ci-C δ- 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-Dirnethylpropyl, 1-Methylpentyl , 2-Methylpentyl, 3-Methyl- pentyl, 4-Methylpentyl, 1, 1-Dimethylbutyl, 1, 2-Dimethylbutyl, 1,3-Dimethylbutyl, 2, 2-Dimethylbutyl, 2, 3-Dimethylbutyl, 3,3-Dimethylbutyl, 1-Ethylbutyl, 2-Ethylbutyl, 1,1,2-Tri- methylpropyl , 1-Ethyl-l-methylpropyl oder 1-Ethyl-3-methylpropyl;C 1 -C 4 -alkyl, as mentioned above, and for example pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2, 2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-dimethylpropyl, 1,2 -Dirnethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1,3-dimethylbutyl, 2, 2-dimethylbutyl, 2, 3-dimethylbutyl , 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1-ethyl-l-methylpropyl or 1-ethyl-3-methylpropyl;
C1-C4-Halogenalkyl: einen Cι-C4-Alkylrest, wie vorstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder Iod substituiert ist, also z.B. Chlormethyl, Dichlormethyl, Trichlormethyl, Fluormethyl, Difluormethyl, Trifluormethyl, Chlorfluormethyl, Dichlorfluormethyl, Chlor- difluormethyl, 2-Fluorethyl, 2-Chlorethyl, 2-Bromethyl, 2-Iodethyl, 2, 2-Difluorethyl, 2, 2, 2-Trifluorethyl, 2-Chlor-2-fluorethyl, 2-Chlor-2, 2-difluorethyl, 2, 2-Dichlor-2-fluorethyl, 2, 2, 2-Trichlorethyl, Pentafluor- ethyl, 2-Fluorpropyl, 3-Fluorpropyl, 2 , 2-Difluorpropyl,C 1 -C 4 -haloalkyl: a Cι-C 4 -alkyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and / or iodine, eg chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl , Chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2, 2-difluoroethyl, 2, 2, 2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro -2, 2-difluoroethyl, 2, 2-dichloro-2-fluoroethyl, 2, 2, 2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2, 2-difluoropropyl,
2, 3-Difluorpropyl, 2-Chlorpropyl, 3-Chlorpropyl, 2,3-Dichlor- propyl, 2-Brompropyl, 3-Brompropyl, 3, 3, 3-Trifluorpropyl, 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; Ci-Cδ-Halogenalkyl, sowie die Halogenalkylteile von N-Ci-Cβ-Halogenalkylamino: Cχ-C4-Halogenalkyl, wie voranstehend genannt, sowie z.B. 5-Fluorpentyl, 5-Chlorpentyl, 5-Brompentyl , 5-Iodpentyl, Undecafluorpentyl, 6-Fluorhexyl, 6-Chlorhexyl, 6-Bromhexyl, 6-Iodhexyl oder Dodecafluorhexyl;2, 3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3, 3, 3-trifluoropropyl, 3, 3, 3-trichloropropyl, 2, 2, 3, 3, 3-pentafluoropropyl, heptafluoropropyl, 1- (fluoromethyl) -2-fluoroethyl, 1- (chloromethyl) -2-chloroethyl, 1- (bromomethyl) -2-bromethyl, 4-fluorobutyl, 4-chlorobutyl, 4- Bromobutyl or nonafluorobutyl; Ci-C δ -haloalkyl, and the haloalkyl parts of N-Ci-Cβ-haloalkylamino: Cχ-C 4 -haloalkyl, as mentioned above, and for example 5-fluoropentyl, 5-chloropentyl, 5-bromopentyl, 5-iodopentyl, undecafluoropentyl, 6-fluorohexyl, 6-chlorohexyl, 6-bromohexyl, 6-iodohexyl or dodecafluorohexyl;
Cι-C4-Alkoxy: z.B. Methoxy, Ethoxy, Propoxy, 1-Methylethoxy, Butoxy, 1-Methylpropoxy, 2-Methylpropoxy oder 1, 1-Dimethyl- ethoxy;-C-C 4 alkoxy: for example methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1, 1-dimethylethoxy;
Cι-C6-Alkoxy, sowie die Alkoxyteile von N-Cι-C6-Alkoxyamino, Di- (Cι-C6-alkoxy)methyl, (Cι-C6 -Alkoxy) (Ci-C6 -alkylthio) - methyl, Cι-C6-Alkoxyimino-Cι-C6-alkyl, N-Cι-C6-Alkoxy- N-Ci-Cδ-alkylamino, N- (Cι-C6-Alkoxy) -N- (Ci-Cβ-alkyl) -amino- carbonyl, N- (C3-C6-Alkenyl) -N- (Ci-Ce-alkoxy) -aminocarbonyl und N- (C3-C6~Alkinyl) -N- (Ci-Cδ-alkoxy) -aminocarbonyl : Cι-C4-Alkoxy, wie voranstehend genannt, sowie z.B. Pentoxy, 1-Methylbutoxy, 2-Methylbutoxy, 3-Methylbutoxy, 1, 1-Dimethyl- propoxy, 1, 2-Dimethylpropoxy, 2, 2-Dimethylpropoxy, 1-Ethyl- propoxy, Hexoxy, 1-Methylpentoxy, 2-Methylpentoxy, 3-Methyl- pentoxy, 4-Methylpentoxy, 1, 1-Dimethylbutoxy, 1,2-Dimethyl- butoxy, 1, 3-Dimethylbutoxy, 2, 2-Dimethylbutoxy, 2, 3-Dimethyl- butoxy, 3, 3-Dimethylbutoxy, 1-Ethylbutoxy, 2-Ethylbutoxy, 1,1, 2-Trimethylpropoxy, 1,2,2-Trimethylpropoxy, 1-Ethyl-l-methylpropoxy oder l-Ethyl-2-methylpropoxy;C 1 -C 6 -alkoxy, and the alkoxy parts of N-C 1 -C 6 -alkoxyamino, di- (C 1 -C 6 -alkoxy) methyl, (C 1 -C 6 -alkoxy) (C 1 -C 6 -alkylthio) - methyl , -CC 6 alkoxyimino -C 6 alkyl, N -C -C 6 alkoxy- N-Ci-C δ -alkylamino, N- (-C 6 alkoxy) -N- (Ci-Cβ -alkyl) -amino-carbonyl, N- (C 3 -C 6 -alkenyl) -N- (Ci-Ce-alkoxy) -aminocarbonyl and N- (C 3 -C 6 -alkynyl) -N- (Ci-C δ -alkoxy) -aminocarbonyl: -CC 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, 1, 1-dimethylbutoxy, 1,2-dimethylbutoxy, 1, 3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1- methylpropoxy or l-ethyl-2-methylpropoxy;
Cχ-C4-Halogenalkoxy: einen Cι-C-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, 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, l-(Chlor- methyl) -2-chlorethoxy, 1- (Brommethyl) -2-bromethoxy, 4-Fluor- butoxy, 4-Chlorbutoxy, 4-Brombutoxy oder Nonafluorbutoxy;Cχ-C 4 -haloalkoxy: a -CC alkoxy, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, bromodifluoromethoxy, 2nd -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 -Dichloro-2-fluoroethoxy, 2,2, 2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 2,2-difluoropropoxy , 2,3-difluoropropoxy, 2, 3-dichloropropoxy, 3, 3, 3-trifluoropropoxy, 3,3, 3-trichloropropoxy, 2, 2, 3, 3, 3-pentafluoropropoxy, heptafluoropropoxy, 1- (fluoromethyl) -2 -fluoroethoxy, l- (chloromethyl) -2-chloroethoxy, 1- (bromomethyl) -2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy;
Ci-Cß-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-C ß -haloalkoxy: -C-C4-haloalkoxy, as mentioned above, and for example 5-fluoropentoxy, 5-chloropentoxy, 5-bromopentoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6-bromohexoxy, 6-iodohexoxy or 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-Cδ-Alkylthio, sowie die Alkylthioteile von Cχ-C6-Alkylthiocarbonyl, Di- (Cι-C6-alkylthio) methyl und (Cχ-C6 -Alkoxy) (Ci-Cβ-alkylthio) methyl: Cι-C4-Alkylthio, wie voranstehend genannt, sowie z.B. Pentylthio, 1-Methylbutyl- thio, 2-Methylb tylthio, 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,Ci-C δ- alkylthio, and the alkylthio parts of Cχ-C 6 -alkylthiocarbonyl, di- (Cι-C 6 -alkylthio) methyl and (Cχ-C 6 -alkoxy) (Ci-Cβ-alkylthio) methyl: Cι-C 4- alkylthio, as mentioned above, and for example pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2, 2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1, 1-dimethylpropylthio, 1 , 2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio,
1,1-Dimethylbutylthio, 1, 2-Dimethylbutylthio, 1, 3-Dimethyl- butylthio, 2, 2-Dimethylb tylthio, 2 , 3-Dimethylbutylthio, 3,3-Dimethylbutylthio, 1-Ethylbutylthio, 2-Ethylb tylthio, 1, 1, 2-Trimethylpropylthio, 1,2, 2-Trimethylpropylthio, 1-Ethyl-l-methylpropylthio oder l-Ethyl-2-methylpropylthio;1,1-dimethylbutylthio, 1, 2-dimethylbutylthio, 1, 3-dimethylbutylthio, 2, 2-dimethylbutylthio, 2, 3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1, 1, 2-trimethylpropylthio, 1,2, 2-trimethylpropylthio, 1-ethyl-l-methylpropylthio or l-ethyl-2-methylpropylthio;
Cι-C4-Halogenalkylthio: einen Cι-C-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-difluorethylthio, 2 , 2-Dichlor-2-fluorethylthio, Pentafluorethylthio, 2-Fluorpropylthio, 3-Fluorpropylthio, 2-Chlorpropylthio, 3-Chlorpropylthio, 2-Brompropylthio, 3-Brompropylthio, 2, 2-Difluorpropylthio, 2, 3-Difluorpropyl- thio, 2,3-Dichlorpropylthio, 3, 3 , 3-Trifluorpropylthio, 3,3,3-Trichlorpropylthio, 2, 2 , 3 ,3, 3-Pentafluorpropylthio, Heptafluorpropylthio, 1- (Fluormethyl) -2-fluorethylthio, 1- (Chlormethyl) -2-chlorethylthio, 1- (Brommethyl) -2-bromethyl- thio, 4-Fluorbutylthio, 4-Chlorbutylthio, 4-Broιributylthio oder Nonafluorb tylthio;C 1 -C 4 haloalkylthio: a C 1 -C 4 -alkylthio radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, bromodifluoromethylthio , 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2, 2-difluoroethylthio, 2, 2, 2-trifluoroethylthio, 2,2,2-trichloroethylthio, 2-chloro-2-fluoroethylthio, 2 -Chlor-2,2-difluoroethylthio, 2, 2-dichloro-2-fluoroethylthio, pentafluoroethylthio, 2-fluoropropylthio, 3-fluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2-bromopropylthio, 3-bromopropylthio, 2, 2-difluor , 2, 3-difluoropropylthio, 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-bromomethylthio, 4-fluorobutylthio, 4-chlorobutylthio, 4-broιributylthio or the Nonafluorb tylthio;
Ci-Cö-Halogenalkylthio: Cι-C4-Halogenalkylthio, wie voranstehend genannt, sowie z.B. 5-Fluorpentylthio, 5-Chlorpen- tylthio, 5-Brompentylthio, 5-Iodpentylthio, Undecafluorpen- tylthio, 6-Fluorhexylthio, 6-Chlorhexylthio, 6-Bromhexylthio, 6-Iodhexylthio oder Dodecafluorhexylthio; Cι-C4-Alkylsulfinyl (Cι*-C4-Alkyl-S (=0) -) : z.B. Methylsulfinyl , Ethylsulfinyl, Propylsulfinyl, 1-Methylethylsulfinyl, Butyl- sulfinyl, 1-Methylpropylsulfinyl, 2-Methylpropylsulfinyl oder 1, 1-Dimethylethylsulfinyl;Ci-C ö -haloalkylthio: -C-C 4 -haloalkylthio, as mentioned above, and for example 5-fluoropentylthio, 5-chloropentylthio, 5-bromopentylthio, 5-iodopentylthio, undecafluoropentylthio, 6-fluorhexylthio, 6-chlorohexylthio, 6-bromohexylthio, 6-iodohexylthio or dodecafluorohexylthio; C 1 -C 4 -alkylsulfinyl (C 1 -C 4 -alkyl-S (= 0) -): e.g. methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl or 1, 1- Dimethylethylsulfinyl;
Cι-C6-Alkylsufinyl (Ci -C6 -Alkyl -S (=0) - ) : C1-C4 -Alkylsulfinyl , wie vorausstehend genannt, sowie Pentylsulfinyl, 1-Methylbu- tylsulfinyl, 2-Methylbutylsulfinyl, 3-Methylbutylsulfinyl, 2,2-Dimethylpropylsulfinyl, 1-Ethylpropylsulfinyl, 1,1-Dime- thylpropylsulfinyl, 1, 2-Dimethylpropylsulfinyl, Hexylsulfi- nyl, 1-Methylpentylsulfinyl, 2-Methylpentylsulfinyl, 3-Me- thylpentylsulfinyl, 4-Methylpentylsulfinyl, 1, 1-Dimethylbu- tylsulfinyl, 1 , 2-Dimethylbutylsulfinyl, 1, 3-Dimethylbutylsul- finyl, 2 , 2-Dimethylbutylsulfinyl, 2 , 3-Dimethylbutylsulfinyl, 3, 3-Dimethylbutylsulfinyl, 1-Ethylbutylsulfinyl, 2-Ethylbu- tylsulfinyl, 1, 1, 2-Trimethylpropylsulfinyl, 1, 2 , 2-Trimethyl- propylsulfinyl, 1-Ethyl-l-methylpropylsulfinyl oder l-Ethyl-2-methylpropylsulfinyl;C 1 -C 6 alkylsufinyl (Ci -C 6 alkyl -S (= 0) -): C 1 -C 4 alkylsulfinyl, as mentioned above, and pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl , 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, 1,1-dimethylpropylsulfinyl, 1, 2-dimethylpropylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl -Dimethylbutylsulfinyl, 1, 2-Dimethylbutylsulfinyl, 1, 3-Dimethylbutylsulfinyl, 2, 2-Dimethylbutylsulfinyl, 2, 3-Dimethylbutylsulfinyl, 3, 3-Dimethylbutylsulfinyl, 1-Ethylbutylsulfinyl, 1-Ethylbutyl , 2-trimethylpropylsulfinyl, 1, 2, 2-trimethylpropylsulfinyl, 1-ethyl-l-methylpropylsulfinyl or l-ethyl-2-methylpropylsulfinyl;
Cι~C4-Halogenalkylsulfinyl : Cι~C4-Alkylsulfinylrest, wie voranstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder Iod substituiert ist, also z.B. Fluormethylsulfinyl, Difluor ethylsulfinyl, 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-Difluorpropylsulfinyl, 2,3-Dichlorpropylsulfinyl, 3 , 3 , 3-Trifluorpropylsulfinyl, 3,3,3-Trichlorpropylsulfinyl, 2, 2, 3 , 3 , 3-Penta- fluorpropylsulfinyl, Heptafluorpropylsulfinyl, 1- (Fluormethyl) -2-fluorethylsulfinyl, 1- (Chlormethyl) -2-chlorethyl- sulfinyl, 1- (Brommethyl) -2-bromethylsulfinyl, 4-Fluorbutyl- sulfinyl, 4-Chlorbutylsulfinyl, 4-Brombutylsulfinyl oder No- nafluorbutylsulfinyl ;Cι ~ C4-haloalkylsulfinyl: which is Cι ~ C4-alkylsulfinyl as mentioned above partially or fully substituted by fluorine, chlorine, bromine and / or iodine, eg fluoromethylsulfinyl, ethylsulfinyl difluoro, trifluoromethyl - sulfinyl, chlorodifluoromethylsulfinyl, Bromdifluormethylsulfi- nyl, 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, pentafluoroethylsulfinyl, 2-fluoropropylsulfinyl, 3-fluoropropylsulfinyl, 2-chloropropylsulfinyl, 3-chloropropylsulfinyl, 2-bromopropylsulfinyl, 3- Bromopropylsulfinyl, 2, 2-difluoropropylsulfinyl, 2, 3-difluoropropylsulfinyl, 2,3-dichloropropylsulfinyl, 3, 3, 3-trifluoropropylsulfinyl, 3,3,3-trichloropropylsulfinyl, 2, 2, 3, 3, 3-pentafluoropropylsulfinyl Heptafluoropropylsulfinyl, 1- (fluoromethyl) -2-fluoroethylsu ifinyl, 1- (chloromethyl) -2-chloroethylsulfinyl, 1- (bromomethyl) -2-bromomethylsulfinyl, 4-fluorobutylsulfinyl, 4-chlorobutylsulfinyl, 4-bromobutylsulfinyl or nonafluorobutylsulfinyl;
Cι-C6-Halogenalkylsulfinyl: Cι-C4-Halogenalkylsulfinyl wie voranstehend genannt, sowie 5-Fluorpentylsulfinyl, 5-Chlor- pentylsulfinyl, 5-Brompentylsulfinyl, 5-Iodpentylsulfinyl, Undecafluorpentylsulfinyl, 6-Fluorhexylsulfinyl, 6-Chlorhe- xylsulfinyl, 6-Bromhexylsulfinyl, 6-Iodhexylsulfinyl oder Dodecafluorhexylsulfinyl; C1-C4-Alkyls lfonyl (Cι-C4-Alkyl-S (=0) 2-) : z.B. Methylsulfonyl, Ethylsulfonyl, Propylsulfonyl, 1-Methylethyl- sulfonyl, Butylsulfonyl, 1-Methylpropylsulfonyl, 2-Methyl- propylsulfonyl oder 1, 1-Dimethylethylsulfonyl;-C-C 6 -Halogenalkylsulfinyl: -C-C 4 -Halogenalkylsulfinyl as mentioned above, and 5-fluoropentylsulfinyl, 5-chloropentylsulfinyl, 5-bromopentylsulfinyl, 5-iodopentylsulfinyl, undecafluoropentylsulfinyl, 6-fluorhexylsulfinyl, 6-chloroheptyl, 6-chloroheptyl Bromhexylsulfinyl, 6-iodohexylsulfinyl or dodecafluorohexylsulfinyl; C 1 -C 4 alkylsfonyl (-C-C 4 alkyl-S (= 0) 2 -): for example methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl or 1, 1-dimethylethylsulfonyl;
Cι-C6-Alkylsulfonyl (Cι-C6-Alkyl-S (=0) 2- ) : C1.-C4-Alkylsulfonyl wie voranstehend genannt, sowie Pentylsulfonyl, 1-Methyl- butylsulfonyl, 2-Methylbutylsulfonyl, 3-Methylb tylsulfonyl, 1, 1-Dimethylpropylsulfonyl , 1, 2-Dimethylpropylsulfonyl , 2, 2-Dirnethylpropylsulfonyl, 1-Ethylpropylsulfonyl, Hexyl- sulfonyl, 1-Methylpentylsulfonyl, 2-Methylpentylsulfonyl, 3-Methylpentylsulfonyl, 4-Methylpentylsulfonyl, 1, 1-Dimethyl- butylsulfonyl, 1, 2-Dimethylbutylsulfonyl, 1, 3-Dimethylb tylsulfonyl, 2,2-Dimethylbutylsulfonyl, 2, 3-Dimethylb tyl- sulfonyl, 3 , 3-Dimethylbutylsulfonyl, 1-Ethylbutylsulfonyl, 2-Ethylbutylsulfonyl, 1, 1, 2-Trimethylpropylsulfonyl, 1,2,2-Trimethylpropylsulfonyl, 1-Ethyl-l-methylpropylsulfonyl oder l-Ethyl-2-methylpropylsulfonyl;C 1 -C 6 -alkylsulfonyl (C 1 -C 6 -alkyl-S (= 0) 2 -): C 1 -C 4 -alkylsulfonyl as mentioned above, and pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3- Methylb tylsulfonyl, 1, 1-Dimethylpropylsulfonyl, 1, 2-Dimethylpropylsulfonyl, 2, 2-Dirnethylpropylsulfonyl, 1-Ethylpropylsulfonyl, Hexylsulfonyl, 1-Methylpentylsulfonyl, 2-Methylpentylsulfonyl, 1-Methylpentylsethyl, 3-Methylpentylsyl - Butylsulfonyl, 1, 2-dimethylbutylsulfonyl, 1, 3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2, 3-dimethylbutylsulfonyl, 3, 3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl Trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-l-methylpropylsulfonyl or l-ethyl-2-methylpropylsulfonyl;
C*ι-C4-Halogenalkylsulfonyl: einen C1-C4-Alkylsulfonylrest, wie voranstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder Iod substituiert ist, also z.B. Fluormethylsulfonyl, Difluormethylsulfonyl, Trifluormethylsulfonyl, Chlordifluormethylsulfonyl, Bromdifluormethylsulfo- nyl, 2-Fluorethylsulfonyl, 2-Chlorethylsulfonyl, 2-Bromethyl- sulfonyl, 2-Iodethylsulfonyl, 2, 2-Difluorethylsulfonyl, 2, 2, 2-Trifluorethylsulfonyl, 2-Chlor-2-fluorethylsulfonyl, 2-Chlor-2,2-difluorethylsulfonyl, 2, 2-Dichlor-2-fluorethylsulfonyl, 2,2,2-Trichlorethylsulfonyl, Pentafluorethyl - sulfonyl, 2-Fluorpropylsulfonyl, 3-Fluorpropylsulfonyl,C * ι-C 4 -haloalkylsulfonyl: a C 1 -C 4 -alkylsulfonyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and / or iodine, eg fluoromethylsulfonyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, Chlordifluormethylsulfonyl, Bromdifluormethylsulfo - nyl, 2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl, 2, 2-difluoroethylsulfonyl, 2, 2, 2-trifluoroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl, 2-chloro-2,2 difluoroethylsulfonyl, 2,2-dichloro-2-fluoroethylsulfonyl, 2,2,2-trichloroethylsulfonyl, pentafluoroethylsulfonyl, 2-fluoropropylsulfonyl, 3-fluoropropylsulfonyl,
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 oder Nonafluorbutylsulfonyl;2-chloropropylsulfonyl, 3-chloropropylsulfonyl, 2-bromopropylsulfonyl, 3-bromopropylsulfonyl, 2, 2-difluoropropylsulfonyl, 2, 3-difluoropropylsulfonyl, 2, 3-dichloropropylsulfonyl, 3,3, 3-trifluoron Trichloropropylsulfonyl, 2, 2, 3, 3, 3-pentafluoropropylsulfonyl, heptafluoropropylsulfonyl, 1- (fluoromethyl) -2-fluoroethylsulfonyl, 1- (chloromethyl) -2-chloroethylsulfonyl, 1- (bromomethyl) -2-bromomethylsulfonyl, 4- Fluorobutylsulfonyl, 4-chlorobutylsulfonyl, 4-bromobutylsulfonyl or nonafluorobutylsulfonyl;
Ci-Cδ-Halogenalkylsulfonyl: Cι-C4-Halogenalkylsulfonyl wie voranstehend genannt, sowie 5-Fluorpentylsulfonyl, 5-Chlor- pentylsulfonyl, 5-Brompentylsulfonyl, 5-Iodpentylsulfonyl, 6-Fluorhexylsulfonyl, 6-Bromhexylsulfonyl, 6-Iodhexylsulfonyl oder Dodecafluorhexylsulfonyl; Ci-Cβ-Alkylamino: z.B. Methylamino, Ethylamino, Propylamino, 1-Methylethylamino, Butylamino, 1-Methylpropylamino, 2-Methylpropylamino, 1, 1-Dimethylethylamino, Pentylamino, 1-Methylbutylamino, 2-Methylbutylamino, 3-Methylbutylamino, 2, 2-Dirnethylpropylamino, 1-Ethylpropylamino, Hexylamino,Ci-C δ -haloalkylsulfonyl: Cι-C 4 -haloalkylsulfonyl as mentioned above, and 5-fluoropentylsulfonyl, 5-chloropentylsulfonyl, 5-bromopentylsulfonyl, 5-iodopentylsulfonyl, 6-fluorhexylsulfonyl, 6-bromhexyl-sulfonyl-hexylsulfonyl; Ci-Cβ-alkylamino: e.g. methylamino, ethylamino, propylamino, 1-methylethylamino, butylamino, 1-methylpropylamino, 2-methylpropylamino, 1, 1-dimethylethylamino, pentylamino, 1-methylbutylamino, 2-methylbutylamino, 3-methylbutylamino, 2 -Dirnethylpropylamino, 1-ethylpropylamino, hexylamino,
1, 1-Dimethylpropylamino, 1, 2-Dirnethylpropylamino, 1-Methyl- pentylamino, 2-Methylpentylamino, 3-Methylpentylamino, 4-Methylpentylamino, 1, 1-Dimethylbutylamino, 1, 2-Dimethyl- butylamino, 1, 3-Dimethylbutylamino, 2, 2-Dimethylbutylamino, 2, 3-Dimethylbutylamino, 3, 3-Dimethylbutylamino, 1-Ethylbutyl- amino, 2-Ethylbutylamino, 1, 1, 2-Trimethylpropylamino, 1,2,2-Trimethylpropylamino, 1-Ethyl-l-methylpropylamino oder l-Ethyl-2-methylpropylamino;1, 1-dimethylpropylamino, 1, 2-dirnethylpropylamino, 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;
Di- (Cι-C-alkyl) amino: z.B. N,N-Dimethylamino, N,N-Diethyl- amino, N,N-Dipropylamino, N,N-Di- (1-methylethyl) - amino, N,N-Dibutylamino, N,N-Di- (1-methylpropyl) amino, N,N-Di- (2-methylpropyl) amino, N,N-Di- (1, 1-dimethylethyl) - amino, N-Ethyl-N-methylamino, N-Methyl-N-propylamino, N-Me- thyl-N- (1-methylethyl) amino, N-Butyl-N-methylamino, N-Me- thyl-N- (1-methylpropyl) amino, N-Methyl-N- (2-methyl- propyl) amino, N- (1, 1-Dimethylethyl) -N-methylamino, N-Ethyl-N- propylamino, N-Ethyl-N- (1-methylethyl) amino, N-Butyl-N-ethyl- amino, N-Ethyl-N- (1-methylpropyl) amino, N-Ethyl-N- (2-methyl - propyl) amino, N-Ethyl-N- (1, 1-dimethylethyl) amino, N-(1-Me- thylethyl) -N-propylamino, N-B tyl-N-propylamino, N-(1-Methyl- propyl) -N-propylamino, N- (2-Methylpropyl) -N-propylamino, N- (1, 1-Dimethylethyl) -N-propylamino, N-Butyl-N- (1-methylethyl) amino, N- (1-Methylethyl) -N- (1-methylpropyl) amino, N- (l-Methylethyl)-N- (2-methylpropyl) amino, N- (1, 1-Dimethylethyl) -N- (1-methylethyl) amino, N-Butyl-N- (1-methylpropyl) - amino, N-Butyl-N- (2-methylpropyl) amino, N-Butyl-N- (1, 1-dimethylethyl) amino, N- (1-Methylpropyl) -N- (2-methylpropyl) -amino, N- (1, 1-Dimethylethyl) -N- (1-methylpropyl) -amino oder N- (1, 1-Dimethylethyl) -N- (2-methylpropyl) amino;Di- (-C-alkyl) amino: e.g. 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-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, NB tyl-N-propylamino, N- (1-methylpropyl) -N-propylamino, N- (2-methylpropyl) -N-propylamino, N- (1, 1-dimethylethyl) -N-propylamino, N-butyl-N- (1-methylethyl) amino, N- (1-methylethyl) -N- (1-methylpropyl) amino, N- (l-methylethyl) -N- (2-methylpropyl) amino, N- ( 1, 1-dimethylethyl) -N- (1-methylethyl) amino, N-butyl-N- (1-methylpr opyl) - 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-CÖ -alkyl) amino: Di- (C1-C4 -alkyl) amino wie voranstehend genannt, sowie N,N-Dipentylamino, N,N-Dihexylamino, N-Methyl- N-pentylamino, N-Ethyl-N-pentylamino, N-Methyl-N-hexylamino oder N-Ethyl-N-hexylamino.Di- (CI-C Ö alkyl) amino: di- (C 1 -C 4 alkyl) amino as mentioned above, and also N, N-dipentylamino, N, N-dihexylamino, 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; Ci-Cδ-Alkylcarbonyl: C1-C4-Alkylcarbonyl, wie voranstehend genannt, sowie z.B. Pentylcarbonyl, 1-Methylbutylcarbonyl, 2-Methylbutylcarbonyl, 3-Methylbutylcarbonyl, 2 , 2-Dimethyl- propylcarbonyl, 1-Ethylpropylcarbonyl, Hexylcarbonyl, 1, 1-Dimethylpropylcarbonyl , 1, 2-Dirnethylpropylcarbonyl,C 1 -C 4 -alkylcarbonyl: for example methylcarbonyl, ethylcarbonyl, propylcarbonyl, 1-methylethylcarbonyl, butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl or 1, 1-dimethylethylcarbonyl; Ci-C δ alkylcarbonyl: 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-Dirnethylpropylcarbonyl,
1-Methylpentylcarbonyl, 2-Methylpentylcarbonyl, 3-Methyl - pentylcarbonyl, 4-Methylpentylcarbonyl, 1, 1-Dimethylbutyl- carbonyl, 1, 2-Dimethylbutylcarbonyl, 1, 3-Dimethylbutyl- carbonyl, 2 , 2 , -Dimethylbutylcarbonyl, 2, 3-Dimethylbutyl- carbonyl, 3 , 3-Dimethylbutylcarbonyl, 1-Ethylbutylcarbonyl, 2-Ethylb tylcarbonyl , 1,1, 2-Trimethylpropylcarbonyl, 1,2, 2-Trimethylpropylcarbonyl , 1-Ethyl-l-methylpropylcarbonyl oder l-Ethyl-2-methylpropylcarbonyl ,-1-methylpentylcarbonyl, 2-methylpentylcarbonyl, 3-methylpentylcarbonyl, 4-methylpentylcarbonyl, 1, 1-dimethylbutylcarbonyl, 1, 2-dimethylbutylcarbonyl, 1, 3-dimethylbutylcarbonyl, 2, 2, -dimethylbutylcarbonyl, 2, 3 -Dimethylbutylcarbonyl, 3, 3-dimethylbutylcarbonyl, 1-ethylbutylcarbonyl, 2-ethylbutylcarbonyl, 1,1, 2-trimethylpropylcarbonyl, 1,2, 2-trimethylpropylcarbonyl, 1-ethyl-l-methylpropylcarbonyl or l-ethyl-2- methylpropylcarbonyl, -
Cι-C4-Halogenalkylcarbonyl: einen C1-C4-Alkylcarbonylrest, wie vorstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder Iod substituiert ist, also z.B. Chloracetyl, Dichloracetyl, Trichloracetyl, Fluoracetyl, Difluoracetyl, Trifluoracetyl, Chlorfluoracetyl, 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, Cι-C4-haloalkylcarbonyl: a C1-C4 alkylcarbonyl as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and / or iodine, ie, for example chloroacetyl, dichloroacetyl, trichloroacetyl, fluoroacetyl, difluoroacetyl, trifluoroacetyl , Chlorofluoroacetyl, dichlorofluoracetyl, chlorodifluoroacetyl, 2-fluoroethylcarbonyl, 2-chloroethylcarbonyl, 2-bromoethylcarbonyl, 2-iodoethylcarbonyl, 2, 2-difluoroethylcarbonyl, 2,2, 2-trifluoroethylcarbonyl, 2-chloro-2-fluoroethylcarbonyl, 2 Chloro-2,2-difluoroethylcarbonyl, 2,2-dichloro-2-fluoroethylcarbonyl, 2,2,2-trichloroethylcarbonyl, pentafluoroethylcarbonyl, 2-fluoropropylcarbonyl,
3-Fluorpropylcarbonyl, 2 , 2-Difluorpropylcarbonyl, 2,3-Diflu- orpropylcarbonyl, 2-Chlorpropylcarbonyl, 3-Chlorpropylcarbo- nyl, 2,3-Dichlorpropylcarbonyl, 2-Brompropylcarbonyl, 3-Brom- propylcarbonyl, 3, 3, 3-Trifluorpropylcarbonyl, 3 , 3, 3-Trichlor- propylcarbonyl, 2, 2, 3, 3, 3-Pentafluorpropylcarbonyl, Heptafluorpropylcarbonyl, 1- (Fluormethyl) -2-fluorethylcarbonyl, 1- (Chlormethyl) -2-chlorethylcarbonyl, 1- (Brommethyl) -2-brome- thylcarbonyl , 4-Fluorbutylcarbonyl, 4-Chlorbutylcarbonyl, 4-Brombutylcarbonyl oder Nonafluorbutylcarbonyl;3-fluoropropylcarbonyl, 2, 2-difluoropropylcarbonyl, 2,3-difluoropropylcarbonyl, 2-chloropropylcarbonyl, 3-chloropropylcarbonyl, 2,3-dichloropropylcarbonyl, 2-bromopropylcarbonyl, 3-bromopropylcarbonyl, 3, 3, 3- Trifluoropropylcarbonyl, 3, 3, 3-trichloropropylcarbonyl, 2, 2, 3, 3, 3-pentafluoropropylcarbonyl, heptafluoropropylcarbonyl, 1- (fluoromethyl) -2-fluoroethylcarbonyl, 1- (chloromethyl) -2-chloroethylcarbonyl, 1- (bromomethyl ) -2-bromothylcarbonyl, 4-fluorobutylcarbonyl, 4-chlorobutylcarbonyl, 4-bromobutylcarbonyl or nonafluorobutylcarbonyl;
Ci-Cö-Halogenalkylcarbonyl: einen Cι-C4-Halogenalkylcarbonyl- rest wie voranstehend genannt, sowie 5-Fluorpentylcarbonyl, 5-Chlorpentylcarbonyl, 5 -Brompentylcarbonyl, Perfluorpentyl- carbonyl, 6-Fluorhexylcarbonyl, 6 -Chlorhexylcarbonyl, 6-Brom- hexylcarbonyl oder Perfluorhexylcarbonyl;Ci-C ö -haloalkylcarbonyl: a Cι-C 4 -haloalkylcarbonyl radical as mentioned above, and 5-fluoropentylcarbonyl, 5-chloropentylcarbonyl, 5-bromopentylcarbonyl, perfluoropentylcarbonyl, 6-fluorhexylcarbonyl, 6 -chlorohexylcarbonyl, 6-bromo-hexylcarbonyl or perfluorohexylcarbonyl;
C1-C4-Alkoxycarbonyl, sowie die Alkoxycarbonylteile von Di- (Cι-C4-alkyl)amino-Cι-C4-alkoxycarbonyl, also z.B. Methoxy- carbonyl, Ethoxycarbonyl, Propoxycarbonyl , 1-Methylethoxy- carbonyl, Butoxycarbonyl , 1-Methylpropoxycarbonyl, 2-Methyl- propoxycarbonyl oder 1, 1-Dirnethylethoxycarbonyl; (Ci-Cg-Alkoxy) carbonyl: (Cι~C -Alkoxy) carbonyl , wie vorstehend genannt, sowie z.B. Pentoxycarbonyl, 1-Methylbutoxycarbonyl, 2-Methylbutoxycarbonyl, 3-Methylbutoxycarbonyl, 2 , 2-Dimethyl- propoxycarbonyl , 1-Ethylpropoxycarbonyl, Hexoxycarbonyl , 1 , 1-Dimethylpropoxycarbonyl , 1 , 2-Dimethylpropoxycarbonyl ,C 1 -C 4 alkoxycarbonyl, and the alkoxycarbonyl parts of di- (-C 4 -alkyl) amino -CC-C 4 -alkoxycarbonyl, ie for example methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, 1-methylethoxycarbonyl, butoxycarbonyl, 1st -Methylpropoxycarbonyl, 2-methyl-propoxycarbonyl or 1, 1-Dirnethylethoxycarbonyl; (Ci-Cg-alkoxy) carbonyl: (-C ~ C -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-Dimethylbutoxycarbonyl, 1, 3-Dimethylbutoxycar- 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-propoxycar- bonyl oder l-Ethyl-2-methyl-propoxycarbonyl;1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1, 1-dimethylbutoxycarbonyl, 1, 2-dimethylbutoxycarbonyl, 1, 3-dimethylbutoxycarbonyl, 2, 2-dimethylbutoxycarbonyl, 2, 3- Dimethylbutoxycarbonyl, 3, 3-dimethylbutoxycarbonyl, 1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl, 1,1, 2-trimethylpropoxycarbonyl, 1,2, 2-trimethylpropoxycarbonyl, 1-ethyl-l-methyl-propoxycarbonyl or l-ethyl- 2-methyl-propoxycarbonyl;
Cι-C4-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, Trifluormetho- xycarbonyl, Chlordifluormethoxycarbonyl, Bromdifluormethoxy- carbonyl, 2-Fluorethoxycarbonyl, 2-Chlorethoxycarbonyl, Cι-C4-haloalkoxycarbonyl: a Cι-C4-alkoxycarbonyl as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and / or iodine, eg Fluormethoxycarbonyl, Difluormethoxycarbonyl, xycarbonyl Trifluormetho-, Chlordifluormethoxycarbonyl, bromodifluoromethoxy carbonyl, 2-fluoroethoxycarbonyl, 2-chloroethoxycarbonyl,
2-Bromethoxycarbonyl, 2-Iodethoxycarbonyl, 2, 2-Difluorethoxy- carbonyl, 2, 2, 2-Trifluorethoxycarbonyl, 2-Chlor-2-bromoethoxycarbonyl, 2-iodoethoxycarbonyl, 2, 2-difluoroethoxycarbonyl, 2, 2, 2-trifluoroethoxycarbonyl, 2-chloro
2-fluorethoxycarbonyl, 2-Chlor-2, 2-difluorethoxycarbonyl,2-fluoroethoxycarbonyl, 2-chloro-2, 2-difluoroethoxycarbonyl,
2, 2-Dichlor-2-fluorethoxycarbonyl, 2,2, 2-Trichlorethoxycarbo- nyl, Pentafluorethoxycarbonyl, 2-Fluorpropoxycarbonyl, 3-Flu- orpropoxycarbonyl , 2-Chlorpropoxycarbonyl, 3-Chlorpropoxycar- bonyl, 2-Brompropoxycarbonyl, 3-Brompropoxycarbonyl, 2,2-Di- fluorpropoxycarbonyl, 2, 3-Difluorpropoxycarbonyl, 2,3-Di- chlorpropoxycarbonyl , 3,3, 3-Trifluorpropoxycarbonyl , 3 , 3 , 3-Trichlorpropoxycarbonyl, 2, 2, 3, 3 , 3-Pentafluorpropoxycarbonyl, Heptafluorpropoxycarbonyl, 1- (Fluormethyl) -2-fluorethoxycarbonyl , 1- (Chlormethyl) -2-chlorethoxycarbonyl , 1- (Brommethyl) -2-bromethoxycarbonyl , 4-Fluorbutoxycarbonyl , 4-Chlorbutoxycarbonyl, 4-Brombutoxycarbonyl oder 4-Iodbutoxy- carbonyl;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 or 4-iodobutoxycarbonyl;
Cι-C6-Halogenalkoxycarbonyl: einen Cι-C4-Halogenalkoxycarbo- nylrest wie voranstehend genannt, sowie 5-Fluorpentoxycarbo- nyl, 5 -Chlorpentoxycarbonyl, 5 -Brompentoxycarbonyl, 6 -Fluor- hexoxycarbonyl, 6-Chlorhexoxycarbonyl oder 6-Bromhexoxycarbo- nyl;C 1 -C 6 haloalkoxycarbonyl: a C 1 -C 4 haloalkoxycarbonyl radical as mentioned above, and 5-fluoropentoxycarbonyl, 5 -chloropentoxycarbonyl, 5-bromopentoxycarbonyl, 6 -fluoro-hexoxycarbonyl, 6-chlorohexoxycarbonyl or 6-bromohexoxycarbonyl or ;
(Cι-C4~Alkyl) carbonyloxy: Acetyloxy, Ethylcarbonyloxy, ' Propyl - carbonyloxy, 1-Methylethylcarbonyloxy, Butylcarbonyloxy, 1-Methylpropylcarbonyloxy, 2-Methylpropylcarbonyloxy oder 1, 1-Dimethylethylcarbonyloxy; (Cι-C4-Alkylamino) carbonyl : z.B. Methylaminocarbonyl , Ethyl- aminocarbonyl, Propylaminocarbonyl, 1-Methylethylaminocarbo- nyl, B tylaminocarbonyl, 1-Methylpropylaminocarbonyl, 2-Me- thylpropylaminocarbonyl oder 1, 1-Dirnethylethylaminocarbonyl;(-C-C 4 ~ alkyl) carbonyloxy: acetyloxy, ethylcarbonyloxy, ' propyl - carbonyloxy, 1-methylethylcarbonyloxy, butylcarbonyloxy, 1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy or 1, 1-dimethylethylcarbonyloxy; (-C-C 4 alkylamino) carbonyl: for example methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl, 1-methylethylaminocarbonyl, B tylaminocarbonyl, 1-methylpropylaminocarbonyl, 2-methylpropylaminocarbonyl or 1, 1-dirnethylethylaminocarbonyl;
(Ci-Cβ-Alkylamino) carbonyl: (Cι-C-Alkylamino) carbonyl, wie vorstehend genannt, sowie z.B. Pentylaminocarbonyl, 1-Methyl - b tylaminocarbonyl, 2-Methylb tylaminocarbonyl, 3-Methylbu- tylaminocarbonyl , 2 , 2-Dimethylpropylaminocarbonyl, 1-Ethyl- propylaminocarbonyl, Hexylaminocarbonyl, 1, 1-Dimethylpropyla- minocarbonyl , 1,2-Dimethylpropylaminocarbonyl, 1-Methylpen- tylaminocarbonyl , 2-Methylpentylaminocarbonyl, 3-Methylpenty- laminocarbonyl , 4-Methylpentylaminocarbonyl , 1, 1-Dimethyl - butylaminocarbonyl , 1 , 2-Dimethylbutylaminocarbonyl, 1 , 3-Di- methylb tylaminocarbonyl , 2 , 2-Dimethylbutylaminocarbonyl,(Ci-Cβ-alkylamino) carbonyl: (-C-C-alkylamino) carbonyl, as mentioned above, and e.g. Pentylaminocarbonyl, 1-methyl-b tylaminocarbonyl, 2-methylb tylaminocarbonyl, 3-methylbutylaminocarbonyl, 2, 2-dimethylpropylaminocarbonyl, 1-ethylpropylaminocarbonyl, hexylaminocarbonyl, 1, 1-dimethylpropyla- minocarbonyl, 1,2-dimethylpropamin Methylpentylaminocarbonyl, 2-methylpentylaminocarbonyl, 3-methylpentylaminocarbonyl, 4-methylpentylaminocarbonyl, 1, 1-dimethylbutylaminocarbonyl, 1, 2-dimethylbutylaminocarbonyl, 1, 3-dimethylbutylaminocarbonyl, 2, 2-dimethylbutylaminocarbonyl
2 , 3-Dimethylbutylaminocarbonyl , 3 , 3-Dimethylbutylaminocarbonyl, 1-Ethylbutylaminocarbonyl, 2-Ethylbutylaminocarbonyl, 1,1, 2-Trimethylpropylaminocarbonyl, 1,2, 2-Trimethylpropylami- nocarbonyl, 1-Ethyl-l-methylpropylaminocarbonyl oder l-Ethyl-2-methylpropylaminocarbonyl;2, 3-dimethylbutylaminocarbonyl, 3, 3-dimethylbutylaminocarbonyl, 1-ethylbutylaminocarbonyl, 2-ethylbutylaminocarbonyl, 1,1, 2-trimethylpropylaminocarbonyl, 1,2, 2-trimethylpropylaminocarbonyl, 1-ethyl-l-methylpropylaminocylyl 2-methylpropylaminocarbonyl;
Di- (Cι-C-alkyl) -aminocarbonyl: z.B. N,N-Dimethylaminocarbonyl, N,N-Diethylaminocarbonyl, N,N-Di- (1-methylethyl) aminocarbonyl, N,N-Dipropylaminocarbonyl, N,N-Dibutylaminocarbo- nyl, N,N-Di- (1-methylpropyl) -aminocarbonyl, N,N-Di- (2-methyl- propyl) -aminocarbonyl, N,N-Di- (1, 1-dimethylethyl) -aminocarbonyl, N-Ethyl-N-methylaminocarbonyl, N-Methyl-N-propyla- minocarbonyl , N-Methyl-N- (1-methylethyl) -aminocarbonyl , N-B - tyl-N-methylaminocarbonyl, N-Methyl-N- (1-methylpropyl) -amino- carbonyl, N-Methyl-N- (2-methylpropyl) -aminocarbonyl,Di- (-C-alkyl) aminocarbonyl: e.g. N, N-dimethylaminocarbonyl, N, N-diethylaminocarbonyl, N, N-di- (1-methylethyl) aminocarbonyl, N, N-dipropylaminocarbonyl, N, N-dibutylaminocarbonyl, N, N-di- (1-methylpropyl) -aminocarbonyl, N, N-di- (2-methyl-propyl) -aminocarbonyl, N, N-di- (1, 1-dimethylethyl) -aminocarbonyl, N-ethyl-N-methylaminocarbonyl, N-methyl-N-propyla - minocarbonyl, N-methyl-N- (1-methylethyl) aminocarbonyl, NB - tyl-N-methylaminocarbonyl, N-methyl-N- (1-methylpropyl) aminocarbonyl, N-methyl-N- (2- methylpropyl) aminocarbonyl,
N- (1 , 1-Dimethylethyl) -N-methylaminocarbonyl, N-Ethyl-N-pro- pylaminocarbonyl, N-Ethyl-N- (1-methylethyl) -aminocarbonyl , N-B tyl-N-ethylaminocarbonyl , N-Ethyl-N- (1-methylpropyl) - aminocarbonyl, N-Ethyl-N- (2-methylpropyl) -aminocarbonyl, N- Ethyl-N- (1, 1-dimethylethyl) -aminocarbonyl, N- (1-Methyl - ethyl) -N-propylaminocarbonyl, N-Butyl-N-propylaminocarbonyl , N- (1-Methylpropyl) -N-propylaminocarbonyl, N- (2-Methyl- propyl) -N-propyl minocarbonyl, N- (1 , 1-Dimethylethyl) -N-pro- pylaminocarbonyl, 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-methylpropyl) -amino- carbonyl oder N- (1, 1-Dimethylethyl) -N- (2-methylpropyl) -aminocarbonyl ;N- (1, 1-dimethylethyl) -N-methylaminocarbonyl, N-ethyl-N-propylaminocarbonyl, N-ethyl-N- (1-methylethyl) aminocarbonyl, NB tyl-N-ethylaminocarbonyl, N-ethyl-N - (1-methylpropyl) - aminocarbonyl, N-ethyl-N- (2-methylpropyl) aminocarbonyl, N-ethyl-N- (1, 1-dimethylethyl) aminocarbonyl, N- (1-methyl-ethyl) -N -propylaminocarbonyl, N-butyl-N-propylaminocarbonyl, N- (1-methylpropyl) -N-propylaminocarbonyl, N- (2-methylpropyl) -N-propylminocarbonyl, 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) -amino-carbonyl, N- (1-methylpropyl) -N- (2-methylpropyl) -aminocarbonyl, N- (1, 1-dimethylethyl) - N- (1-methylpropyl) amino carbonyl or N- (1, 1-dimethylethyl) -N- (2-methylpropyl) aminocarbonyl;
Di- (Ci-Cβ-alkyl) -aminocarbonyl: Di- (Cι-C4-alkyl) -amino- carbonyl, wie voranstehend genannt, sowie z.B. N-Methyl- N-pentylaminocarbonyl, N-Methyl-N- (1-methylbutyl) -aminocarbonyl, N-Methyl-N- (2-methylb tyl) -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) -aminocarbonyl, N-Methyl-N- (3-methylpentyl) -aminocarbonyl, N-Me- thyl-N- (4-methylpentyl) -aminocarbonyl, N-Methyl-N-Di- (Ci-Cβ-alkyl) -aminocarbonyl: di- (-C-C 4 -alkyl) -amino-carbonyl, as mentioned above, and for example N-methyl-N-pentylaminocarbonyl, N-methyl-N- (1- methylbutyl) aminocarbonyl, N-methyl-N- (2-methylb tyl) aminocarbonyl, N-methyl-N- (3-methylbutyl) aminocarbonyl, N-methyl-N- (2,2-dimethylpropyl) aminocarbonyl, N-methyl-N- (1-ethylpropyl) aminocarbonyl, N-methyl-N-hexylaminocarbonyl, N-methyl-N- (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- b tyl) -aminocarbonyl, N-Methyl-N- (1, 3-dimethylb tyl) -aminocarbonyl , N-Methyl-N- (2 , 2-dimethylbutyl) -aminocarbonyl , N-Me- thyl-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-methylb tyl) -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- dimethylb tyl) -aminocarbonyl, N-Ethyl-N- (3 , 3-dimethylbutyl) - aminocarbonyl, N-Ethyl-N- (1-ethylbutyl) -aminocarbonyl, N- Ethyl-N- (2-ethylbutyl) -aminocarbonyl, N-Ethyl-N- (1, 1, 2-tri- methylpropyl) -aminocarbonyl, N-Ethyl-N- (1,2, 2-trimethyl - propyl) -aminocarbonyl, N-Ethyl-N- (1-ethyl-l-methyl- propyl) -aminocarbonyl, N-Ethyl-N- (l-ethyl-2-methyl- propyl) -aminocarbonyl, N-Propyl-N-pentylaminocarbonyl, N-Butyl-N-pentylaminocarbonyl, N,N-Dipentylaminocarbonyl, N-Propyl-N-hexylaminocarbonyl , N-Butyl-N-hexylaminocarbonyl , N-Pentyl-N-hexylaminocarbonyl oder N,N-Dihexylaminocarbonyl;(1, 1-dimethylbutyl) aminocarbonyl, N-methyl-N- (1, 2-dimethyl-butyl) aminocarbonyl, N-methyl-N- (1, 3-dimethylbutyl) aminocarbonyl, N-methyl- N- (2, 2-dimethylbutyl) aminocarbonyl, N-methyl-N- (2, 3-dimethylbutyl) aminocarbonyl, N-methyl-N- (3, 3-dimethylbutyl) aminocarbonyl, N-methyl- N- (1-ethyl-butyl) aminocarbonyl, N-methyl-N- (2-ethylbutyl) aminocarbonyl, N-methyl-N- (1, 1, 2-trimethylpropyl) aminocarbonyl, N-methyl-N- (1, 2, 2-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-methylb tyl) 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-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-dimethyl-butyl) -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-Cβ-alkyl) -ammothiocarbonyl: z.B. N,N-Dimethylamino- thiocarbonyl, N,N-Diethylaminothiocarbonyl, N,N-Di- (1-methylethyl) ammothiocarbonyl, N,N-Dipropylaminothiocarbonyl , N,N-Dibutylaminothiocarbonyl, N,N-Di- (1-methylpropyl) -amino- thiocarbonyl, N,N-Di- (2-methylpropyl) -aminothiocarbonyl, N,N-Di- (1, 1-dimethylethyl) -aminothiocarbonyl, N-Ethyl-N-me- thylaminothiocarbonyl, N-Methyl-N-propylaminothiocarbonyl, N- Methyl-N- (1-methylethyl) -aminothiocarbonyl, N-B tyl-N-methyl - aminothiocarbonyl, N-Methyl-N- (1-methylpropyl) -aminothiocarbonyl , N-Methyl-N- (2-methylpropyl) -aminothiocarbonyl , N- (1, 1-Dimethylethyl) -N-methylaminothiocarbonyl, N-Ethyl- N-propylaminothiocarbonyl, N-Ethyl-N- (1-methylethyl) -aminothiocarbonyl , N-Butyl-N-ethylaminothiocarbonyl, N- Ethyl-N- (1-methylpropyl) -aminothiocarbonyl, N-Ethyl-N- (2-me- thylpropyl) -aminothiocarbonyl , N-Ethyl-N- (1, 1-dimethyl - ethyl) -aminothiocarbonyl , N- (1-Methylethyl) -N-propylamino- thiocarbonyl, N-Butyl-N-propylaminothiocarbonyl, N-(1-Methyl- propyl) -N-propylaminothiocarbonyl, N- (2-Methylpropyl) -N-propylaminothiocarbonyl , N- (1, 1-Dimethylethyl) -N-propylamino- thiocarbonyl, N-Butyl-N- (1-methylethyl) -aminothiocarbonyl , N- (1-Methylethyl) -N- (1-methylpropyl) -aminothiocarbonyl, N- (1-Methylethyl) -N- (2-methylpropyl) -aminothiocarbonyl,Di- (Ci-Cβ-alkyl) -ammothiocarbonyl: e.g. N, N-dimethylaminothiocarbonyl, N, N-diethylaminothiocarbonyl, N, N-di- (1-methylethyl) ammothiocarbonyl, N, N-dipropylaminothiocarbonyl, N, N-dibutylaminothiocarbonyl, N, N-di- (1-methylpropyl) -amino-thiocarbonyl, N, N-di- (2-methylpropyl) -aminothiocarbonyl, N, N-di- (1, 1-dimethylethyl) -aminothiocarbonyl, N-ethyl-N-methylaminothiocarbonyl, N-methyl-N -propylaminothiocarbonyl, N-methyl-N- (1-methylethyl) -aminothiocarbonyl, NB tyl-N-methyl - aminothiocarbonyl, N-methyl-N- (1-methylpropyl) -aminothiocarbonyl, N-methyl-N- (2-methylpropyl ) -aminothiocarbonyl, N- (1, 1-dimethylethyl) -N-methylaminothiocarbonyl, N-ethyl-N-propylaminothiocarbonyl, N-ethyl-N- (1-methylethyl) -aminothiocarbonyl, N-butyl-N-ethylaminothiocarbonyl, N- Ethyl-N- (1-methylpropyl) aminothiocarbonyl, N-ethyl-N- (2-methylpropyl) aminothiocarbonyl, N-ethyl-N- (1, 1-dimethyl-ethyl) -aminothiocarbonyl, N- (1 -Methylethyl) -N-propylamino-thiocarbonyl, N-butyl-N-propylaminothiocarbonyl, N- (1-methyl-propyl) - N-propylaminothiocarbonyl, N- (2-methylpropyl) -N-propylaminothiocarbonyl, N- (1, 1-dimethylethyl) -N-propylamino-thiocarbonyl, N-butyl-N- (1-methylethyl) aminothiocarbonyl, N- (1 -Methylethyl) -N- (1-methylpropyl) aminothiocarbonyl, N- (1-methylethyl) -N- (2-methylpropyl) aminothiocarbonyl,
N- (1, 1-Dimethylethyl) -N- (1-methylethyl) -aminothiocarbonyl, N- Butyl-N- (1-methylpropyl) -aminothiocarbonyl , N-Butyl-N- (2-me- thylpropyl) -aminothiocarbonyl, N-Butyl-N- (1, 1-dimethyl - ethyl) -aminothiocarbonyl, N- (1-Methylpropyl ) -N- (2-methyl- propyl) -aminothiocarbonyl, N- (1, 1-Dimethylethyl) -N- (1-methyl- propyl) -aminothiocarbonyl, N- (1, 1-Dimethylethyl) -N- (2-methyl- propyl) -aminothiocarbonyl , N-Methyl-N-pentylaminothiocarbo- nyl, N-Methyl-N- (1-methylbutyl) -aminothiocarbonyl, N-Methyl-N- (2-methylbutyl) -aminothiocarbonyl, N-Methyl-N- (3-me- thylbutyl) -aminothiocarbonyl , N-Methyl-N- (2 , 2-dimethyl - propyl) -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-methyl- pentyl) -aminothiocarbonyl, N-Methyl-N- (3-methylpentyl) -amino- thiocarbonyl, N-Methyl-N- (4-methylpentyl) -aminothiocarbonyl, N-Methyl-N- (1, 1-dimethylbutyl) -aminothiocarbonyl, N-Methyl- N- (1, 2-dimethylbutyl) -aminothiocarbonyl, N-Methyl-N- (1,3- dimethylbutyl) -aminothiocarbonyl, N-Methyl-N- (2 , 2-dimethylbutyl) -aminothiocarbonyl , N-Methyl-N- (2 , 3-dimethylbutyl) - aminothiocarbonyl, N-Methyl-N- (3 , 3-dimethylbutyl) -aminothio- carbonyl , N-Methyl-N- (1-e hylbutyl) -aminothiocarbonyl , N-Me- thyl-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) -aminothiocarbonyl, N- Ethyl-N- (2-methylbutyl) -aminothiocarbonyl, N-Ethyl-N- (3- methylbutyl) -aminothiocarbonyl, N-Ethyl-N- (2 , 2-dimethyl- propyl) -aminothiocarbonyl, N-Ethyl-N- (1-ethylpropyl) -aminothiocarbonyl , N-Ethyl-N-hexylaminothiocarbonyl, N-Ethyl-N- (1, 1-dimethylpropyl) -aminothiocarbonyl, N-Ethyl-N- (1,2- dimethylpropyl) -aminothiocarbonyl, N-Ethyl-N- (1-methyl- pentyl) -aminothiocarbonyl, N-Ethyl-N- (2-methylpentyl) -amino- thiocarbonyl, N-Ethyl-N- (3-methylpentyl) -aminothiocarbonyl, N-Ethyl-N- (4-methylpentyl) -aminothiocarbonyl, N-Ethyl-N- (1, 1-dimethylbutyl) -aminothiocarbonyl, N-Ethyl-N- (1, 2- dimethylb tyl) -aminothiocarbonyl, N-Ethyl-N- (1, 3-dimethylbutyl) -aminothiocarbonyl, N-Ethyl-N- (2, 2-dimethylbutyl) - aminothiocarbonyl, N-Ethyl-N- (2 , 3-dimethylbutyl) -aminothiocarbonyl, N-Ethyl-N- (3, 3-dimethylbutyl) -aminothiocarbonyl, N- Ethyl-N- (1-ethylb tyl) -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;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-methyl-propyl) -aminothiocarbonyl, N- (1, 1-dimethylethyl) -N- (2-methyl-propyl) -aminothiocarbonyl, N-methyl-N-pentylaminothiocarbonyl, N-methyl-N- (1 -methylbutyl) -aminothiocarbonyl, N-methyl-N- (2-methylbutyl) -aminothiocarbonyl, N-methyl-N- (3-methylbutyl) -aminothiocarbonyl, N-methyl-N- (2, 2-dimethyl-propyl ) -aminothiocarbonyl, N-methyl-N- (1-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) - aminothiocarbon yl, N-methyl-N- (4-methylpentyl) aminothiocarbonyl, N-methyl-N- (1, 1-dimethylbutyl) aminothiocarbonyl, N-methyl-N- (1, 2-dimethylbutyl) aminothiocarbonyl, N- Methyl-N- (1,3-dimethylbutyl) aminothiocarbonyl, N-methyl-N- (2, 2-dimethylbutyl) aminothiocarbonyl, N-methyl-N- (2, 3-dimethylbutyl) aminothiocarbonyl, N-methyl N- (3, 3-dimethylbutyl) aminothio- carbonyl, N-methyl-N- (1-e hylbutyl) 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-pentylaminothiocarbonyl, N-ethyl-N- (1-methylbutyl) aminothiocarbonyl, N-ethyl-N- (2-methylbutyl) aminothiocarbonyl, N-ethyl -N- (3-methylbutyl) aminothiocarbonyl, N-ethyl-N- (2,2-dimethylpropyl) aminothiocarbonyl, N-ethyl-N- (1-ethylpropyl) aminothiocarbonyl, N-ethyl-N-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) -amino-thiocarbonyl, N-ethyl-N- (3-methylpentyl) -aminothiocarbonyl, N-ethyl-N- (4-methylpentyl) -aminothiocarbonyl, N-ethyl-N- ( 1, 1-dimethylbutyl ) -aminothiocarbonyl, N-ethyl-N- (1, 2-dimethylb tyl) -aminothiocarbonyl, N-ethyl-N- (1, 3-dimethylbutyl) -aminothiocarbonyl, N-ethyl-N- (2, 2-dimethylbutyl) aminothiocarbonyl, N-ethyl-N- (2, 3-dimethylbutyl) -aminothiocarbonyl, N-ethyl-N- (3, 3-dimethylbutyl) -aminothiocarbonyl, N-ethyl-N- (1-ethylb tyl) -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- pentylaminothiocarbonyl, N-butyl-N-pentylaminothiocarbonyl, N, N-dipentylamino-thiocarbonyl, N-propyl-N-hexylaminothiocarbonyl, N-butyl-N-hexylaminothiocarbonyl, N-pentyl-N-hexylaminothiocarbonyl or N, N
Cχ-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, (l-Methylpropoxy)methoxy, (2-Methylpropoxy)methoxy, (1, l-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,Cχ-C 4 -alkoxy-C 4 ~ alkoxy, and the alkoxyalkoxy parts of -C-C 4 alkoxy-Cι-C 4 -alkoxycarbonyl: by -C ~ C 4 -alkoxy, as mentioned above, substituted -CC 4 - Alkoxy, e.g. for methoxymethoxy, ethoxymethoxy, propoxymethoxy, (1-methylethoxy) methoxy, butoxymethoxy, (l-methylpropoxy) methoxy, (2-methylpropoxy) methoxy, (1, l-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- (propoxy) propoxy, 2- (1-methylethoxy) propoxy,
2- (Butoxy) -propoxy, 2- (1-Methylpropoxy) propoxy, 2- (2-Methyl - propoxy) propoxy, 2- (1, 1-Dimethylethoxy) 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-(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,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-methylpropoxy) butoxy, 3- (2-methylpropoxy) butoxy, 3- (1, 1-dimethylethoxy) butoxy, 4- (methoxy) butoxy, 4- (ethoxy) butoxy, 4- (propoxy) butoxy, 4- (1-methylethoxy) butoxy,
4- (Butoxy) butoxy, 4- (1-Methylpropoxy) butoxy, 4-(2-Methyl- propoxy)butoxy oder 4- (1, 1-Dimethylethoxy)butoxy;4- (butoxy) butoxy, 4- (1-methylpropoxy) butoxy, 4- (2-methylpropoxy) butoxy or 4- (1, 1-dimethylethoxy) butoxy;
C3-C6-Alkenyl, sowie die Alkenylteile von C3-C6-Alkenyl- carbonyl, C3-C6"Alkenyloxy, C3-C6-Alkenyloxycarbonyl,C 3 -C 6 alkenyl, and the alkenyl parts of C 3 -C 6 alkenylcarbonyl, C 3 -C 6 "alkenyloxy, C 3 -C 6 alkenyloxycarbonyl,
C3-C6-Alkenylaminocarbonyl, N- (C3-C6-Alkenyl) -N- (Cι-C6) alkyl - aminocarbonyl, N- (C3-Cδ-Alkenyl) -N- (Cι-C6-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, l-Methyl-but-3-en-l-yl, 2-Methyl- but-3-en-l-yl, 3-Methyl-but-3-en-l-yl, 1, 1-Dimethyl- prop-2-en-l-yl, 1, 2-Dimethyl-prop-2-en-l-yl, 1-Ethyl- prop-2-en-l-yl, Hex-3-en-l-yl, Hex-4-en-l-yl, Hex-5-en-l-yl, l-Methyl-pent-3-en-l-yl, 2-Methyl-pent-3-en-l-yl, 3-Methyl- pent-3-en-l-yl, 4-Methyl-pent-3-en-l-yl, 1-Methyl- pent-4-en-l-yl, 2-Methyl-pent-4-en-l-yl, 3-Methyl- pent-4-en-l-yl, 4-Methyl-pent-4-en-l-yl, 1, 1-Dimethyl- but-2-en-l-yl, 1, l-Dimethyl-but-3-en-l-yl, 1, 2-Dimethyl- but-2-en-l-yl, 1, 2-Dimethyl-but-3-en-l-yl, 1, 3-Dimethyl- but-2-en-l-yl, 1, 3-Dimethyl-but-3-en-l-yl, 2, 2-Dimethyl- but-3-en-l-yl, 2, 3-Dimethyl-but-2-en-l-yl, 2, 3-Dimethyl- but-3-en-l-yl, 3, 3-Dimethyl-but-2-en-l-yl, l-Ethyl-but-2- en-l-yl, l-Ethyl-but-3-en-l-yl, 2-Ethyl-but-2-en-l-yl, 2-Ethyl-but-3-en-l-yl, 1, 1, 2-Trimethyl-prop-2-en-l-yl, l-Ethyl-l-methyl-prop-2-en-l-yl oder l-Ethyl-2-methyl- prop-2-en-l-yl ;C 3 -C 6 alkenylaminocarbonyl, N- (C 3 -C 6 alkenyl) -N- (Cι-C 6 ) alkyl - aminocarbonyl, N- (C 3 -C δ- alkenyl) -N- (Cι-C 6- alkoxy) aminocarbonyl: for example prop-2-en-1-yl, but-1-en-4-yl, 1-methyl-prop-2-en-1-yl, 2-methyl-prop-2-ene -l-yl, 2-butene-l-yl, l-penten-3-yl, l-penten-4-yl, 2-penten-4-yl, 1-methyl-but-2-en-l-yl , 2-methyl-but-2-en-l-yl, 3-methyl-but-2-en-l-yl, l-methyl-but-3-en-l-yl, 2-methyl-but-3 -en-1-yl, 3-methyl-but-3-en-1-yl, 1, 1-dimethyl-prop-2-en-1-yl, 1, 2-dimethyl-prop-2-en-1 -yl, 1-ethyl-prop-2-en-1-yl, hex-3-en-1-yl, hex-4-en-1-yl, hex-5-en-1-yl, 1-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-1-yl, 2-methyl-pent-4-en-1-yl, 3-methyl-pent-4-en-1-yl, 4-methyl-pent -4-en-1-yl, 1, 1-dimethyl-but-2-en-1-yl, 1, l-dimethyl-but-3-en-1-yl, 1, 2-dimethyl-but-2 -en-1-yl, 1, 2-dimethyl-but-3-en-1-yl, 1, 3-dimethyl-but-2-en-1-yl, 1, 3-dimethyl-but-3-ene -l-yl, 2,2-dimethylbut-3-en-l-yl, 2,3-dimethyl -but-2-en-1-yl, 2, 3-dimethyl-but-3-en-1-yl, 3, 3-dimethyl-but-2-en-1-yl, 1-ethyl-but-2 - en-1-yl, 1-ethyl-but-3-en-1-yl, 2-ethyl-but-2-en-1-yl, 2-ethyl-but-3-en-1-yl, 1 , 1, 2-Trimethyl-prop-2-en-l-yl, l-ethyl-l-methyl-prop-2-en-l-yl or l-ethyl-2-methyl-prop-2-en-l -yl;
- C2-C6-Alkenyl, sowie die Alkenylteile von C2-C6-Alkenyl- carbonyl, Phenyl-C2-C6-alkenylcarbonyl und Heterocyclyl- C-C6 _alkenylcarbonyl : C3-C6~Alkenyl, wie voranstehend genannt, sowie Ethenyl;- C 2 -C 6 alkenyl, and the alkenyl parts of C 2 -C 6 alkenylcarbonyl, phenyl-C 2 -C 6 -alkenylcarbonyl and heterocyclyl- CC 6 _ alkenylcarbonyl: C 3 -C 6 ~ alkenyl, as above called, as well as ethenyl;
- C3-C6-Halogenalkenyl: einen C3-C6-Alkenylrest, wie vorstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder Iod substituiert ist, also z.B. 2-Chlorallyl, 3-Chlorallyl, 2, 3-Dichlorallyl, 3, 3-Dichlorallyl, 2,3,3-Tri- chlorallyl, 2, 3-Dichlorbut-2-enyl, 2-Bromallyl, 3-Bromallyl, 2, 3-Dibromallyl, 3, 3-Dibromallyl, 2 , 3, 3-Tribromallyl oder 2 , 3-Dibrombut-2-enyl ;C 3 -C 6 haloalkenyl: a C 3 -C 6 alkenyl radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example 2-chloroallyl, 3-chlorallyl, 2, 3-dichlorallyl, 3, 3-dichlorallyl, 2,3,3-trichlorallyl, 2, 3-dichlorobut-2-enyl, 2-bromoallyl, 3-bromoallyl, 2, 3-dibromoallyl, 3, 3-dibromoallyl, 2, 3, 3-tribromoallyl or 2,3-dibromobut-2-enyl;
C3-C6-Alkinyl, sowie die Alkinylteile von C3-C6-Alkinyl- carbonyl, C3-C6-Alkinyloxy, C3-C6-Alkinyloxycarbony, C3-C6-Al- kinylaminocarbonyl, N- (C3-C6-Alkinyl) -N- (Cι-C6- alkyl) -aminocarbonyl, N- (C3-C6-Alkinyl) -N- (Cι-C6-alkoxy- aminocarbonyl: z.B. Propargyl, But-l-in-3-yl, But-l-in-4-yl, But-2-in-l-yl, Pent-l-in-3-yi, Pent-l-in-4-yl, Pent-1-in- 5-yl, Pent-2-in-l-yl, Pent-2-in-4-yl, Pent-2-in-5-yl, 3-Me- thyl-but-l-in-3-yl, 3-Methyl-but-l-in-4-yl, Hex-l-in-3- yl, Hex-l-in-4-yl, Hex-l-in-5-yl, Hex-l-in-6-yl, Hex-2-in-l- yl, Hex-2-in-4-yl, Hex-2-in-5-yl, Hex-2-in-6-yl, Hex-3-in-C 3 -C 6 alkynyl, and the alkynyl parts of C 3 -C 6 alkynylcarbonyl, C 3 -C 6 alkynyloxy, C 3 -C6 alkynyloxycarbonyl, C 3 -C 6 alkynylaminocarbonyl, N- ( C 3 -C 6 alkynyl) -N- (-C-C 6 -alkyl) -aminocarbonyl, N- (C 3 -C 6 -alkynyl) -N- (-C-C 6 -alkoxy-aminocarbonyl: for example propargyl, but -l-in-3-yl, but-l-in-4-yl, but-2-in-l-yl, pent-l-in-3-yi, pent-l-in-4-yl, pent -1-in-5-yl, pent-2-in-1-yl, pent-2-in-4-yl, pent-2-in-5-yl, 3-methyl-but-l-in -3-yl, 3-methyl-but-l-in-4-yl, hex-l-in-3-yl, hex-l-in-4-yl, hex-l-in-5-yl, hex -l-in-6-yl, hex-2-in-1-yl, hex-2-in-4-yl, hex-2-in-5-yl, hex-2-in-6-yl, hex -3-in
1-yl, Hex-3-in-2-yl, 3-Methyl-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;
C-Cδ-Alkinyl, sowie die Alkinylteile von C -C6~Alkinyl- carbonyl: C-C6-Alkinyl, wie voranstehend genannt, sowie Ethinyl;CC δ alkynyl, and the alkynyl parts of C 6 -C 6 alkynylcarbonyl: CC 6 alkynyl, as mentioned above, and ethynyl;
C3-C6-Halogenalkinyl: einen C3-C6-Alkinylrest, wie vorstehend genannt, der partiell oder vollständig durch Fluor, Chlor, Brom und/oder Iod substituiert ist, also z.B. 1,1-Difluor- prop-2-in-l-yl, 3-Iod-prop-2-in-l-yl, 4-Fluorbut-2-in-l-yl, 4-Chlorbut-2-in-l-yl, 1, 1-Difluorbut-2-in-l-yl, 4-Iod- but-3-in-l-yl, 5-Fluorpent-3-in-l-yl, 5-Iod-pent-4-in-l-yl, 6-Fluor-hex-4-in-l-yl oder 6-Iod-hex-5-in-l-yl;C 3 -C 6 haloalkynyl: a C 3 -C 6 alkynyl radical, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, for example 1,1-difluoroprop-2- in-l-yl, 3-iodo-prop-2-in-l-yl, 4-fluorobut-2-in-l-yl, 4-chlorobut-2-in-l-yl, 1, 1-difluorobut- 2-in-l-yl, 4-iodobut-3-in-l-yl, 5-fluoropent-3-in-l-yl, 5-iodo-pent-4-in-l-yl, 6- Fluoro-hex-4-in-1-yl or 6-iodo-hex-5-in-1-yl;
C3-C6-Cycloalkyl, sowie die Cycloalkylteile von C3-C6-Cyclo- alkylcarbonyl : z.B. Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl ;C 3 -C 6 cycloalkyl, and the cycloalkyl parts of C 3 -C 6 cycloalkylcarbonyl: for example cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;
Heterocyclyl, sowie Heterocyclylteile von Heterocyclylcarbonyl, Heterocyclyl-Ci-Cε-alkyl, Heterocyclyloxycarbonyl, Heterocyclyloxythiocarbonyl, Heterocyclylcarbonyl-Ci-Cö-alkyl, N- (Cχ-C6-Alkyl) -N- (heterocyclyl) -aminocarbonyl, Heterocyclyl - aminocarbonyl: ein gesättigter, partiell gesättigter oder un- gesättiger 5- oder 6-gliedriger, C-gebundener, hetero- cyclischer Ring, der ein bis vier gleiche oder verschiedene Heteroatome, ausgewählt aus folgender Gruppe: Sauerstoff, Schwefel oder Stickstoff, enthält, also z.B. 5-gliedrige Ringe wie: 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, 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,Heterocyclyl, and also heterocyclyl parts of heterocyclylcarbonyl, heterocyclyl-Ci-Cε-alkyl, heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl, heterocyclylcarbonyl-Ci-C ö -alkyl, N- (Cχ-C 6 -alkyl) -l-, -aminocyyl : 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, ie, for example 5-link rings such as: Tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydrothien-2-yl, tetrahydrothien-3-yl, tetrahydropyrrol-2-yl, tetrahydropyrrol-3-yl, 2, 3-dihydrofuran-2-yl, 2, 3-dihydrofuran-3-yl, 2,5-dihydrofuran-2-yl, 2,5-dihydrofuran-3-yl, 4,5-dihydrofuran-2-yl, 4,5-dihydrofuran-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,5-dihydrothien-2-yl, 2,5-dihydrothien-3-yl, 4,5-dihydrothien-2- yl, 4,5-dihydrothien-3-yl, 2,3-dihydro-lH-pyrrol-2-yl, 2,3-dihydro-lH-pyrrol-3-yl, 2,5-dihydro-lH-pyrrole 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, Pyrrol-3-yl, Tetrahydropyrazol-3-yl, Tetrahydropyrazol-4-yl, Tetrahydroisoxazol-3-yl, Tetrahydroisoxazol-4-yl, Tetrahy- droisoxazol-5-yl, 1, 2-Oxathiolan-3-yl, 1, 2-Oxathiolan-4-yl, 1, 2-Oxathiolan-5-yl, Tetrahydroisothiazol-3-yl, Tetrahydro- isothiazol-4-yl, Tetrahydroisothiazol-5-yl, 1, 2-Dithiolan-3- yl, 1, 2-Dithiolan-4-yl, Tetrahydroimidazol-2-yl, Tetrahydro- imidazol-4-yl, Tetrahydrooxazol-2-yl, Tetrahydrooxazol-4-yl, Tetrahydrooxazol-5-yl, Tetrahydrothiazol-2-yl, Tetrahydro- thiazol-4-yl, Tetrahydrothiazol-5-yl, 1, 3-Dioxolan-2-yl, l,3-Dioxolan-4-yl, 1, 3-Oxathiolan-2-yl, 1, 3-Oxathiolan-4-yl, l,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,3,4-dihydro-2H-pyrrol-2-yl, 3,4-dihydro-2H-pyrrol-3-yl, 3,4-dihydro-5H-pyrrol-2-yl, 3,4-dihydro-5H- pyrrol-3-yl, 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, pyrrol-2-yl, pyrrol-3-yl, tetrahydropyrazol-3-yl, tetrahydropyrazol-4-yl, tetrahydroisoxazol-3- yl, tetrahydroisoxazol-4-yl, tetrahydroisoxazol-5-yl, 1, 2-oxathiolan-3-yl, 1, 2-oxathiolan-4-yl, 1, 2-oxathiolan-5-yl, tetrahydroisothiazol-3- yl, tetrahydro-isothiazol-4-yl, tetrahydroisothiazol-5-yl, 1, 2-dithiolan-3-yl, 1, 2-dithiolan-4-yl, tetrahydroimidazol-2-yl, 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 3-dioxolan-4-yl, 1,3-oxathiolan-2-yl, 1,3-oxathiolan-4-yl, 1,3-oxathiolan-5-yl, 1,3-dithiolan-2-yl, 1,1 3-dithiolan-4-yl, 4,5-dihydro-lH-pyrazol-3-yl, 4,5-dihydro-lH-pyrazol-4-yl,
4, 5-Dihydro-lH-pyrazol-5-yl, 2, 5-Dihydro-lH-pyrazol-3-yl, 2, 5-Dihydro-lH-pyrazol-4-yl, 2 , 5-Dihydro-lH-pyrazol-5-yl,4,5-dihydro-lH-pyrazol-5-yl, 2,5-dihydro-lH-pyrazol-3-yl, 2,5-dihydro-lH-pyrazol-4-yl, 2,5-dihydro-lH- pyrazol-5-yl,
4, 5-Dihydroisoxazol-3-yl, 4, 5-Dihydroisoxazol-4-yl, 4,5-Dihy- droisoxazol-5-yl, 2, 5-Dihydroisoxazol-3-yl, 2, 5-Dihydroisoxa- zol-4-yl, 2, 5-Dihydroisoxazol-5-yl, 2, 3-Dihydroisoxazol-3-yl, 2, 3-Dihydroisoxazol-4-yl, 2, 3-Dihydroisoxazol-5-yl, 4,5-Dihy- droisothiazol-3-yl, 4, 5-Dihydroisothiazol-4-yl, 4,5-Dihydro- isothiazol-5-yl, 2, 5-Dihydroisothiazol-3-yl, 2, 5-Dihydroiso- thiazol-4-yl, 2, 5-Dihydroisothiazol-5-yl, 2 , 3-Dihydroisothia- zol-3-yl, 2, 3-Dihydroisothiazol-4-yl, 2, 3-Dihydroisothiazol- 5-yl, Δ3-l,2-Dithiol-3-yl, Δ3-l, 2-Dithiol-4-yl, Δ3-1,2-Di- thiol-5-yl, 4, 5-Dihydro-lH-imidazol-2-yl, 4, 5-Dihydro-lH-imi- dazol-4-yl, 4, 5-Dihydro-lH-imidazol-5-yl, 2, 5-Dihydro-lH-imi- dazol-2-yl, 2, 5-Dihydro-lH-imidazol-4-yl, 2 , 5-Dihydro-lH-imi- dazol-5-yl, 2, 3-Dihydro-lH-imidazol-2-yl, 2 , 3-Dihydro-lH-imi- dazol-4-yl, 4, 5-Dihydrooxazol-2-yl, 4, 5-Dihydrooxazol-4-yl, 4, 5-Dihydrooxazol-5-yl, 2, 5-Dihydrooxazol-2-yl, 2,5-Dihydro- oxazol-4-yl, 2, 5-Dihydrooxazol-5-yl, 2, 3-Dihydrooxazol-2-yl, 2,3-Dihydrooxazol-4-yl, 2, 3-Dihydrooxazol-5-yl, 4,5-Dihydro- thiazol-2-yl, 4, 5-Dihydrothiazol-4-yl, 4, 5-Dihydrothia- zol-5-yl, 2,5-Dihydrothiazol-2-yl, 2, 5-Dihydrothiazol-4-yl, 2,5-Dihydrothiazol-5-yl, 2, 3-Dihydrothiazol-2-yl, 2,3-Dihy- drothiazol-4-yl, 2, 3-Dihydrothiazol-5-yl, 1, 3-Dioxol-2-yl, l,3-Dioxol-4-yl, 1, 3-Dithiol-2-yl, 1, 3-Dithiol-4-yl, 1,3-Oxa- thiol-2-yl, 1, 3-Oxathiol-4-yl, 1, 3-Oxathiol-5-yl, Pyrazol-3- yl, Pyrazol-4-yl, Isoxazol-3-yl, Isoxazol-4-yl, lsoxazol-5- yl, Isothiazol-3-yl, Isothiazol-4-yl, Isothiazol-5-yl, Imidazol-2-yl, Imidazol-4-yl, Oxazol-2-yl, Oxazol-4-yl, Oxazol-5-yl, Thiazol-2-yl, Thiazol-4-yl, Thiazol-5-yl,4,5-dihydroisoxazol-3-yl, 4,5-dihydroisoxazol-4-yl, 4,5-dihydroisoxazol-5-yl, 2,5-dihydroisoxazol-3-yl, 2,5-dihydroisoxazol- 4-yl, 2,5-dihydroisoxazol-5-yl, 2,3-dihydroisoxazol-3-yl, 2,3-dihydroisoxazol-4-yl, 2,3-dihydroisoxazol-5-yl, 4,5-dihy- droisothiazol-3-yl, 4,5-dihydroisothiazol-4-yl, 4,5-dihydro-isothiazol-5-yl, 2,5-dihydroisothiazol-3-yl, 2,5-dihydroisothiazol-4-yl, 2, 5-dihydroisothiazol-5-yl, 2, 3-dihydroisothiazol-3-yl, 2, 3-dihydroisothiazol-4-yl, 2, 3-dihydroisothiazol-5-yl, Δ 3 -l, 2-dithiol -3-yl, Δ 3 -l, 2-dithiol-4-yl, Δ 3 -1,2-di-thiol-5-yl, 4, 5-dihydro-1H-imidazol-2-yl, 4, 5 Dihydro-lH-imidazol-4-yl, 4,5-dihydro-lH-imidazol-5-yl, 2,5-dihydro-lH-imidazol-2-yl, 2,5-dihydro-lH imidazol-4-yl, 2,5-dihydro-lH-imidazol-5-yl, 2,3-dihydro-lH-imidazol-2-yl, 2,3-dihydro-lH-imidazol-4 -yl, 4,5-dihydrooxazol-2-yl, 4,5-dihydrooxazol-4-yl, 4,5-dihydrooxazol-5-yl, 2,5-dihydrooxazol-2-yl, 2,5-dihydrooxazole -4-yl, 2,5-dihydrooxazol-5-yl, 2nd , 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-dihy- drothiazol-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, oxazole 2-yl, oxazol-4-yl, oxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl,
1.2, 3-Δ2-0xadiazolin-4-yl , 1,2, 3-Δ2-0xadiazolin-5-yl , 1,2, 4-Δ-Oxadiazolin-3-yl , 1,2, 4-Δ-Oxadiazolin-5-yl , l,2,4-Δ2-0xadiazolin-3-yl, 1, 2 , 4-Δ2-0xadiazolin-5-yl, 1,2, 4-Δ3-Oxadiazolin-3-yl , 1,2 , 4-Δ3-Oxadiazolin-5-yl , 1,3, 4-Δ2-Oxadiazolin-2-yl , 1,3, 4-Δ2-θxadiazolin-5-yl,1.2, 3-Δ 2 -0xadiazolin-4-yl, 1,2, 3-Δ 2 -0xadiazolin-5-yl, 1,2, 4-Δ-oxadiazolin-3-yl, 1,2, 4-Δ- Oxadiazolin-5-yl, l, 2,4-Δ 2 -0xadiazolin-3-yl, 1, 2, 4-Δ 2 -0xadiazolin-5-yl, 1,2, 4-Δ 3 -oxadiazolin-3-yl , 1,2, 4-Δ 3 -oxadiazolin-5-yl, 1,3, 4-Δ 2 -oxadiazolin-2-yl, 1,3, 4-Δ 2 -θxadiazolin-5-yl,
1.3, 4-Δ3-Oxadiazolin-2-yl , 1,3, 4-Oxadiazolin-2-yl , 1,2, 4-Δ4-Thiadiazolin-3-yl , 1,2, 4-Δ-Thiadiazolin-5-yl, l,2,4-Δ3-Thiadiazolin-3-yl, 1, 2, 4-Δ3-Thiadiazolin-5-yl, 1,2, 4-Δ2-τhiadiazolin-3-yl , 1,2, 4-Δ2-Thiadiazolin-5-yl , l,3,4-Δ2-τhiadiazolin-2-yl, 1, 3, 4-Δ2-Thiadiazolin-5-yl, 1,3, 4-Δ3-Thiadiazolin-2-yl , 1,3, 4-Thiadiazolin-2-yl, l,3,2-Dioxathiolan-4-yl, 1, 2 , 3-Δ2-Triazolin-4-yl, l,2,3-Δ2-Triazolin-5-yl, 1, 2, 4-Δ2-Triazolin-3-yl, 1,2, 4-Δ2-Triazolin-5-yl , 1,2, 4-Δ3-Triazolin-3-yl , l,2,4-Δ3-Triazolin-5-yl, 1, 2 , 4-Δ1-Triazolin-2-yl, 1,2,4-Tri- azolin-3-yl, 3H-1, 2,4-Dithiazol-5-yl, 2H-1, 3, 4-Dithiazol-5- yl, 2H-l,3,4-Oxathiazol-5-yl, 1, 2, 3-Oxadiazol-4-yl, l,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, 1,2, 4-Triazol-3-yl, Tetrazol-5-yl,1.3, 4-Δ 3 -oxadiazolin-2-yl, 1,3, 4-oxadiazolin-2-yl, 1,2, 4-Δ 4 -thiiaziaz-3-yl, 1,2, 4-Δ-thiadiazolin- 5-yl, l, 2,4-Δ 3 -thiadiazolin-3-yl, 1, 2, 4-Δ 3 -thiadiazolin-5-yl, 1,2, 4-Δ 2 -τhiadiazolin-3-yl, 1st , 2, 4-Δ 2 -Thiadiazolin-5-yl, l, 3,4-Δ 2 -τhiadiazolin-2-yl, 1, 3, 4-Δ 2 -Thiadiazolin-5-yl, 1,3, 4- Δ 3 -thiadiazolin-2-yl, 1,3, 4-thiadiazolin-2-yl, l, 3,2-dioxathiolan-4-yl, 1, 2, 3-Δ 2 -triazolin-4-yl, l, 2,3-Δ 2 -triazolin-5-yl, 1, 2, 4-Δ 2 -triazolin-3-yl, 1,2, 4-Δ 2 -triazolin-5-yl, 1,2, 4-Δ 3- triazolin-3-yl, l, 2,4-Δ 3 -triazolin-5-yl, 1, 2, 4-Δ 1 -triazolin-2-yl, 1,2,4-triazolin-3- yl, 3H-1, 2,4-dithiazol-5-yl, 2H-1, 3, 4-dithiazol-5- yl, 2H-l, 3,4-oxathiazol-5-yl, 1, 2, 3- Oxadiazol-4-yl, l, 2,3-oxadiazol-5-yl, 1,2,4-oxadiazol-3-yl, 1,2,4, -oxadiazol-5-yl, 1,3,4-oxadiazole -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-thiazedia-2-yl, 1,2,3-triazol-4-yl, 1,2,4-triazol-3-yl, Te trazol-5-yl,
6-gliedrige Ringe wie:6-link rings such as:
Tetrahydropyran-2-yl, Tetrahydropyran-3-yl, Tetrahydro- pyran-4-yl, Piperidin-2-yl, Piperidin-3-yl, Piperidin-4-yl, Tetrahydrothiopyran-2-yl, Tetrahydrothiopyran-3-yl, Tetra- hydrothiopyran-4-yl, 2H-3 , 4-Dihydropyran-6-yl , 2H-3 , 4-Dihydropyran-5-yl , 2H-3 , 4-Dihydropyran-4-yl , 2H-3 , 4-Dihydropyran-3-yl , 2H-3 , -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, l,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, , 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, l,2-Dihydropyridin-3-yl, 1, 2-Dihydropyridin-4-yl, l,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,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, -dihydropyran-2-yl, 2H-3,4-dihydropyran-6-yl, 2H-3,4-dihydrothiopyran-5-yl, 2H-3, 4-dihydrothiopyran-4 -yl, 2H-3,4,4-dihydropyran-3-yl, 2H-3,4,4-dihydropyran-2-yl, 1,2,3,4-tetrahydropyridin-6-yl, 1,2,3,4-tetrahydropyridine -5-yl, 1,2,3, 4-tetrahydropyridin-4-yl, l, 2,3,4-tetrahydropyridin-3-yl, 1, 2, 3, 4-tetrahydropyridin-2-yl, 2H -5, 6-dihydropyran-2-yl, 2H-5, 6-dihydropyran-3-yl, 2H-5, 6-dihydropyran-4-yl, 2H-5, 6-dihydropyran-5-yl, 2H-5 , 6-dihydropyran-6-yl, 2H-5, 6-dihydrothiopyran-2-yl, 2H-5, 6-dihydrothiopyran-3-yl, 2H-5, 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,, 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-dihydropyridine-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-dihydropyridine -6-yl, 3,4-dihydropyridin-2-yl, 3,4-dihydr opyridin-3-yl, 3,4-dihydropyridin-4-yl, 3,4-dihydropyridin-5-yl, 3,4-dihydropyridin-6-yl, 2,5-dihydropyridin-2-yl, 2,5- Dihydropyridin-3-yl, 2,5-dihydropyridin-4-yl,
2, 5-Dihydropyridin-5-yl, 2, 5-Dihydropyridin-6-yl, 2, 3-Dihydropyridin-2-yl, 2, 3-Dihydropyridin-3-yl, 2, 3-Dihydropyridin-4-yl, 2, 3-Dihydropyridin-5-yl, 2,3-Dihydropyridin-6-yl, Pyridin-2-yl, Pyridin-3-yl, Pyridin-4-yl, 1, 3-Dioxan-2-yl, 1, 3-Dioxan-4-yl, 1,3-Dioxan-2, 5-dihydropyridin-5-yl, 2, 5-dihydropyridin-6-yl, 2, 3-dihydropyridin-2-yl, 2, 3-dihydropyridin-3-yl, 2, 3-dihydropyridin-4-yl, 2, 3-dihydropyridin-5-yl, 2,3-dihydropyridin-6-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, 1, 3-dioxan-2-yl, 1, 3-dioxan-4-yl, 1,3-dioxane
5-yl, l,4-Dioxan-2-yl, 1, 3-Dithian-2-yl, 1, 3-Dithian-4-yl, l,3-Dithian-5-yl, 1, 4-Dithian-2-yl, 1, 3-Oxathian-2-yl, l,3-Oxathian-4-yl, 1, 3-Oxathian-5-yl, 1, 3-Oxathian-6-yl, l,4-Oxathian-2-yl, 1, 4-Oxathian-3-yl, 1, 2-Dithian-3-yl, 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-l,3-thiazin-2-yl, Tetrahydro-1, 3-thiazin-4-yl, Tetra- hydro-1, 3-thiazin-5-yl, Tetrahydro-1, 3-thiazin-6-yl, Tetra- hydro-1, 4-thiazin-2-yl, Tetrahydro-1, 4-thiazin-3-yl, Tetra- hydro-1, 4-oxazin-2-yl, Tetrahydro-1, 4-oxazin-3-yl, Tetra- hydro-l,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-l,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-l,2-thiazin-3-yl, 4H-5, 6-Dihydro-l, 2-thiazin-4-yl, 4H-5 , 6-Dihydro-l , 2-thiazin-5-yl, 4H-5 , 6-Dihydro-l , 2-thia- zin-6-yl, 2H-3, 6-Dihydro-l, 2-oxazin-3-yl, 2H-3, 6-Dihydro- l,2-oxazin-4-yl, 2H-3, 6-Dihydro-l, 2-oxazin-5-yl, 2H-3,6-Di- hydro-1, 2-oxazin-6-yl, 2H-3, 6-Dihydro-l, 2-thiazin-3-yl,5-yl, l, 4-dioxan-2-yl, 1, 3-dithian-2-yl, 1, 3-dithian-4-yl, l, 3-dithian-5-yl, 1, 4-dithian 2-yl, 1, 3-oxathian-2-yl, l, 3-oxathian-4-yl, 1, 3-oxathian-5-yl, 1, 3-oxathian-6-yl, l, 4-oxathian 2-yl, 1,4-oxathian-3-yl, 1,2-dithian-3-yl, 1,2-dithian-4-yl, hexahydropyrimidin-2-yl, hexahydropyrimi-din-4-yl, hexahydropyrimidine 5-yl, hexahydropyrazin-2-yl, hexahydropyridazin-3-yl, hexahydropyridazin-4-yl, tetrahydro-1, 3-oxazin-2-yl, tetrahydro-1, 3-oxazin-4-yl, tetra- hydro-1, 3-oxazin-5-yl, tetrahydro-1, 3-oxazin-6-yl, tetrahydro-l, 3-thiazin-2-yl, tetrahydro-1, 3-thiazin-4-yl, Tetrahydro-1,3-thiazin-5-yl, tetrahydro-1,3-thiazin-6-yl, tetrahydro-1,4-thiazin-2-yl, tetrahydro-1,4-thiazin-3- yl, tetrahydro-1, 4-oxazin-2-yl, tetrahydro-1, 4-oxazin-3-yl, tetrahydro-l, 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-oxazin-6-yl, 2H-5, 6-dihydro-l, 2-thiazin-3-yl, 2H-5,6-dihydro-l, 2-thiazine 4-yl, 2H-5, 6-dihydro-l, 2-thiazin-5-yl, 2H-5,6-dihydro-l, 2-thiazin-6-yl, 4H-5, 6-dihydro-l, 2-oxazin-3-yl, 4H-5, 6-dihydro-l, 2-oxazin-4-yl, 4H-5, 6-dihydro-l, 2-oxazin-5-yl, 4H-5, 6-dihydro-l, 2-oxazin-6-yl, 4H-5,6-di- hydro-l, 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-l, 2-oxazin- 4-yl, 2H-3, 6-dihydro-l, 2-oxazin-5-yl, 2H-3,6-dihydro-1, 2-oxazin-6-yl, 2H-3, 6-dihydro- l, 2-thiazin-3-yl,
2H-3 , 6-Dihydro-l , 2-thiazin-4-yl, 2H-3 , 6-Dihydro-l , 2-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- l,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,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-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-thiazin-4-yl, 2H-3,4, 4-dihydro-l, 2-thiazin-5-yl, 2H-3,4, 4-dihydro-l, 2-thiazine 6-yl, 2,3,4, 5-tetrahydropyridazin-3-yl, 2,3,4, 5-tetrahydropyridazin-4-yl, 2,3,4, 5-tetrahydropyridazin-5-yl, 2, 3, 4, 5-tetrahydropyridazin-6-yl, 3, 4, 5, 6-tetrahydropyridazin-3-yl, 3, 4, 5, 6-tetrahydropyridazin-4-yl,
1, 2, 5, 6-Tetrahydropyridazin-3-yl, 1,2 , 5, 6-Tetrahydropyrida- zin-4-yl, 1, 2 , 5, 6-Tetrahydropyridazin-5-yl, 1, 2 , 5, 6-Tetrahy- dropyridazin-6-yl , 1,2,3, 6-Tetrahydropyridazin-3-yl, 1, 2, 3, 6-Tetrahydropyridazin-4-yl, 4H-5, 6-Dihydro-l, 3-oxa- zin-2-yl, 4H-5, 6-Dihydro-l, 3-oxazin-4-yl, 4H-5,6-Di- hydro-1, 3-oxazin-5-yl, 4H-5, 6-Dihydro-l, 3-oxazin-6-yl, 4H-5 , 6-Dihydro-l , 3-thiazin-2-yl, 4H-5 , 6-Dihydro-l , 3-thia- zin-4-yl, 4H-5, 6-Dihydro-l, 3-thiazin-5-yl, 4H-5, 6-Dihydro- l,3-thiazin-6-yl, 3,4, 5-6-Tetrahydropyrimidin-2-yl, 3,4, 5,6-Tetrahydropyrimidin-4-yl, 3, 4, 5, 6-Tetrahydro- pyrimidin-5-yl, 3, 4, 5, 6-Tetrahydropyrimidin-6-yl, 1,2,3,4-Te- trahydropyrazin-2-yl, 1,2,3, 4-Tetrahydropyrazin-5-yl, 1,2,3, 4-Tetrahydropyrimidin-2-yl, 1,2,3, 4-Tetrahydropyrimi - din-4-yl, 1, 2, 3, 4-Tetrahydropyrimidin-5-yl, 1, 2, 3,4-Tetra- hydropyrimidin-6-yl, 2, 3-Dihydro-l, 4-thiazin-2-yl, 2,3-Di- hydro-l,4-thiazin-3-yl, 2, 3-Dihydro-l, 4-thiazin-5-yl, 2,3-Di- hydro-l,4-thiazin-6-yl, 2H-l,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-l,2-Oxazin-4-yl, 4H-1, 2-Oxazin- 5-yl, 4H-l,2-Oxazin-6-yl, 4H-1, 2-Thiazin-3-yl, 4H-1,2-Thia- zin-4-yl, 4H-1, 2-Thiazin-5-yl, 4H-1, 2-Thiazin-6-yl, 6H-l,2-Oxazin-3-yl, 6H-1, 2-Oxazin-4-yl, 6H-1, 2-Oxazin-5-yl, 6H-l,2-Oxazin-6-yl, 6H-l,2-Thiazin-3-yl, 6H-1, 2-Thiazin-4-yl, 6H-l,2-Thiazin-5-yl, 6H-1, 2-Thiazin-6-yl, 2H-1, 3-Oxazin-2-yl, 2H-l,3-Oxazin-4-yl, 2H-1, 3-Oxazin-5-yl, 2H-1, 3-Oxazin-6-yl, 2H-l,3-Thiazin-2-yl, 2H-1, 3-Thiazin-4-yl, 2H-1, 3-Thiazin-5- yl, 2H-l,3-Thiazin-6-yl, 4H-1, 3-Oxazin-2-yl, 4H-1, 3-Oxazin- 4-yl, 4H-l,3-Oxazin-5-yl, 4H-1, 3-Oxazin-6-yl, 4H-1,3-Thiazin- 2-yl, 4H-l,3-Thiazin-4-yl, 4H-1, 3-Thiazin-5-yl, 4H-1,3-Thia- zin-6-yl, 6H-l,3-Oxazin-2-yl, 6H-1, 3-Oxazin-4-yl, 6H-l,3-Oxa- zin-5-yl, 6H-1, 3-Oxazin-6-yl, 6H-1, 3-Thiazin-2-yl, 6H-l,3-Oxazin-4-yl, 6H-1, 3-Oxazin-5-yl, 6H-1, 3-Thiazin-6-yl, 2H-l,4-Oxazin-2-yl, 2H-1, 4-Oxazin-3-yl, 2H-1, 4-Oxazin-5-yl, 2H-l,4-Oxazin-6-yl, 2H-1, -Thiazin-2-yl, 2H-1, 4-Thiazin-3-yl, 2H-l,4-Thiazin-5-yl, 2H-1, 4-Thiazin-6-yl, 4H-1, 4-Oxazin-2-yl, 4H-l,4-Oxazin-3-yl, 4H-1, 4-Thiazin-2-yl, 4H-1, 4-Thiazin-3-yl, 1, 4-Dihydropyridazin-3-yl, 1, 4-Dihydropyridazin-4-yl, 1,4-Di- hydropyridazin-5-yl, 1, 4-Dihydropyridazin-6-yl, 1,4-Dihydro- pyrazin-2-yl, 1, 2-Dihydropyrazin-2-yl, 1, 2-Dihydropyrazin- 3-yl, l,2-Dihydropyrazin-5-yl, 1, 2-Dihydropyrazin-6-yl, 1, 4-Dihydropyrimidin-2-yl, 1, 4-Dihydropyrimidin-4-yl, 1,4-Di- hydropyrimidin-5-yl, 1, 4-Dihydropyrimidin-6-yl, 3,4-Dihydro- pyrimidin-2-yl , 3 , 4-Dihydropyrimidin-4-yl , 3 , 4-Dihydropyrimi - din-5-yl oder 3, 4-Dihydropyrimidin-6-yl, Pyridazin-3-yl, Pyridazin-4-yl, Pyrimidin-2-yl, Pyrimidin-4-yl, Pyrimidin-5- yl, Pyrazin-2-yl, 1, 3, 5-Triazin-2-yl, 1, 2 , 4-Triazin-3-yl, l,2,4-Triazin-5-yl, 1,2, 4-Triazin-6-yl, 1, 2, 4, 5-Tetra- zin-3-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- oxazine-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-thiazine-4- yl, 4H-5, 6-dihydro-l, 3-thiazin-5-yl, 4H-5, 6-dihydro-l, 3-thiazin-6-yl, 3,4, 5-6-tetrahydropyrimidin-2- yl, 3,4, 5,6-tetrahydropyrimidin-4-yl, 3, 4, 5, 6-tetrahydropyrimidin-5-yl, 3, 4, 5, 6-tetrahydropyrimidin-6-yl, 1,2, 3,4-tetrahydropyrazin-2-yl, 1,2,3, 4-tetrahydropyrazin-5-yl, 1,2,3, 4-tetrahydropyrimidin-2-yl, 1,2,3, 4-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-di-hydro-l, 4-thiazine 6-yl, 2H-1, 2-oxazin-3-yl, 2H-1, 2-oxazin-4-yl, 2H-1, 2-oxazin-5-yl, 2H-1, 2-oxazin-6-yl, 2H- 1, 2-thiazin-3-yl, 2H-1, 2-thiazin-4-yl, 2H-1, 2-thiazin-5-yl, 2H-1, 2-thiazine-6-yl, 4H-1, 2-oxazin-3-yl, 4H-l, 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-l, 2-thiazine 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-l, 3-oxazin-4-yl, 2H-1, 3-oxazin-5-yl, 2H-1, 3-oxazin-6-yl, 2H-l, 3-thiazin-2-yl, 2H-1, 3-thiazin-4-yl, 2H-1, 3-thiazin-5- yl, 2H-1, 3-thiazin-6-yl, 4H-1, 3-oxazin-2-yl, 4H- 1, 3-oxazin-4-yl, 4H-l, 3-oxazin-5-yl, 4H-1, 3-oxazin-6-yl, 4H-1,3-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-1, 3-oxazin-5-yl, 6H-1, 3-oxazin-6-yl, 6H-1, 3-thiazin-2-yl, 6H-l, 3-oxazin-4-yl, 6H-1, 3-oxazin-5-yl, 6H-1, 3-thiazin-6-yl, 2H-l, 4-oxazin-2-yl, 2H- 1, 4-oxazin-3-yl, 2H-1, 4-oxazin-5-yl, 2H-1, 4-oxazin-6-yl, 2H-1, -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-oxazine -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, l, 2-dihydropyrazin-5-yl, 1, 2-dihydropyrazin-6-yl, 1, 4-dihydropyrimidin-2-yl, 1, 4-dihydropyrimidin-4-yl, 1,4-dihydropyrimidine -5-yl, 1,4-dihydropyrimidin-6-yl, 3,4-dihydropyrimidin-2-yl, 3,4-dihydropyrimidin-4-yl, 3,4-dihydropyrimi-din-5-yl or 3rd , 4-dihydropyrimidin-6-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl, 1, 3, 5 -Triazin-2-yl, 1, 2, 4-triazin-3-yl, l, 2,4-triazin-5-yl, 1,2, 4-triazin-6-yl, 1, 2, 4, 5 -Tetrazin- 3-yl;
wobei ggf. der Schwefel der genannten Heterocyclen zu S=0 oder S(=0)2 oxidiert sein kann;where appropriate the sulfur of the heterocycles mentioned can be oxidized to S = 0 or S (= 0) 2 ;
und wobei mit einem ankondensierten Phenylring oder mit einem C3-C6-Carbocyclus oder mit einem weiteren 5- bis 6-gliedrigen Heterocyclus ein bicyclisches Ringsystem ausgebildet werden kann.and a bicyclic ring system can be formed with a fused-on phenyl ring or with a C 3 -C 6 carbocycle or with a further 5- to 6-membered heterocycle.
N-gebundenes Heterocyclyl: ein gesättigter, partiell gesättigter oder ungesättigter 5- oder 6-gliedriger N-gebundener heterocyclischer Ring, der mindestens einen Stickstoff und gegebenenfalls ein bis drei gleiche oder verschiedene Hetero- atome, ausgewählt aus folgender Gruppe: Sauerstoff, Schwefel oder Stickstoff enthält, also z.B.N-linked heterocyclyl: a saturated, partially saturated or unsaturated 5- or 6-membered N-linked heterocyclic ring, the at least one nitrogen and optionally one to three identical or different hetero atoms, selected from the following group: oxygen, sulfur or nitrogen contains, e.g.
N-gebundene 5-gliedrige Ringe wie: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, 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-θxa- diazolin-4-yl, 1, 2, 4-Δ3-Oxadiazolin-2-yl, 1, 3,4-Δ-θxadiazo- 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-τhiadiazo- 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;Tetrahydropyrrol-1-yl, 2,3-dihydro-lH-pyrrol-l-yl, 2,5-di-hydro-lH-pyrrol-1-yl, pyrrol-1-yl, tetrahydropyrazol-1-yl, tetrahydroisoxazole 2-yl, tetrahydroisothiazol-2-yl, tetrahydroimidazol-1-yl, tetrahydrooxazol-3-yl, tetrahydrothiazol-3-yl, 4,5-dihydro-lH-pyrazol-l-yl, 2,5- Dihydro-lH-pyrazol-l-yl, 2,3-dihydro-lH-pyrazol-l-yl, 2,5-dihydroisoxazol-2-yl, 2,3-dihydroisoxazol-2-yl, 2,5- Dihydroisothiazol-2-yl, 2,3-dihydroisoxazol-2-yl, 4,5-dihydro-lH-imidazol-l-yl, 2,5-dihydro-lH-imidazol-l-yl, 2,3-dihydro 1H-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 -θxadiazolin-4-yl, 1, 2, 4-Δ 3 -oxadiazolin-2-yl, 1, 3,4-Δ-θxadiazo- 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 -τhiadiazo-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-l,3-thiazin-3-yl, Tetrahydro-1, 4-thiazin-4-yl, Tetra- hydro-1, 4-oxazin-4-yl, Tetrahydro-1, 2-oxazin-2-yl, 2H-5,6-Di- hydro-1, 2-oxazin-2-yl, 2H-5, 6-Dihydro-l, 2-thiazin-2-yl, 2H-3,6-Dihydro-l,2-oxazin-2-yl, 2H-3, 6-Dihydro-l, 2-thiazin- 2-yl, 2H-3,4-Dihydro-oxazin-2-yl, 2H-3, 4-Dihydro-l, 2-thiazin- 2-yl, 2,3,4, 5-Tetrahydropyridazin-2-yl, 1,2, 5, 6-Tetrahydropy- ridazin-1-yl, 1, 2, 5, 6-Tetrahydropyridazin-2-yl, 1,2,3,6-Te- trahydropyridazin-1-yl , 3,4,5, 6-Tetrahydropyrimidin-3-yl, 1,2,3, 4-Tetrahydropyrazin-l-yl , 1,2,3, 4-Tetrahydro- pyrimidin-1-yl, 1, 2 ,3, 4-Tetrahydropyrimidin-3-yl, 2,3-Dih- dro-l,4-thiazin-4-yl, 2H-1, 2-Oxazin-2-yl, 2H-1, 2-Thiazin- 2-yl, 4H-l,4-Oxazin-4-yl, 4H-1, 4-Thiazin-4-yl, 1, 4-Dihydropy- ridazin-1-yl, 1, 4-Dihydropyrazin-l-yl, 1, 2-Dihydropyra- zin-l-yl, 1,4-Dihydropyrimidin-l-yl oder 3, 4-Dihydropyrimi- din-3-yl, sowie N-gebundene cyclische Imide wie: Phthalsäureimid, Tetrahydrophthalsäureimid, Succinimid, Ma- leinimid oder Glutarimid;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-l, 3-thiazin-3- yl, tetrahydro-1, 4-thiazin-4-yl, tetrahydro-1, 4-oxazin-4-yl, tetrahydro-1, 2-oxazin-2-yl, 2H-5,6-dihydro 1, 2-oxazin-2-yl, 2H-5, 6-dihydro-l, 2-thiazin-2-yl, 2H-3,6-dihydro-l, 2-oxazin-2-yl, 2H-3, 6-dihydro-l, 2-thiazine-2-yl, 2H-3,4-dihydro-oxazin-2-yl, 2H-3,4, 4-dihydro-l, 2-thiazine-2-yl, 2,3, 4, 5-tetrahydropyridazin-2-yl, 1,2, 5, 6-tetrahydropyridazin-1-yl, 1, 2, 5, 6-tetrahydropyridazin-2-yl, 1,2,3,6-te- trahydropyridazin-1-yl, 3,4,5, 6-tetrahydropyrimidin-3-yl, 1,2,3, 4-tetrahydropyrazin-l-yl, 1,2,3, 4-tetrahydropyrimidin-1-yl, 1, 2, 3, 4-tetrahydropyrimidin-3-yl, 2,3-dihydro-l, 4-thiazin-4-yl, 2H-1, 2-oxazin-2-yl, 2H-1, 2- Thiazin-2-yl, 4H-l, 4-oxazin-4-yl, 4H-1, 4-thiazin-4-yl, 1, 4-dihydropyridazin-1-yl, 1, 4-dihydropyrazine-l-yl, 1, 2-dihydropyrazine-l-yl, 1,4-dihydropyrimidin-l-yl or 3, 4-dihydropyrimidine-3-yl, and N-linked cyclic imides such as: phthalimide, tetrahydrophthalimide, succinimide, maleimide or glutarimide;
Alle Phenylringe bzw. Heterocyclylreste sowie alle Phenylkompo- nenten in Phenyl-alkyl, Phenylcarbonyl-alkyl, Phenylcarbonyl , Phenylalkylcarbonyl, Phenylalkenylcarbonyl, Phenoxycarbonyl, Phe- nyloxythiocarbonyl, Phenylammocarbonyl, N-Alkyl-N-phenylaminocarbonyl, Phenylsulfonyl und Phenoxysulfonyl bzw. alle Heterocyc- lylkomponenten in Heterocyclyl-alkyl, Heterocyclylcarbonyl-alkyl, Heterocyclylcarbonyl, Heterocyclylalkylcarbonyl, Heterocyclylal- kenylcarbonyl, Heterocyclyloxycarbonyl , Heterocyclyloxythiocarbo- nyl, Heterocyclylaminocarbonyl , N-Alkyl-N-heterocyclylaminocarbo- nyl, Heterocyclylsulfonyl und Heterocyclyloxysulfonyl sind, soweit nicht anders angegeben, vorzugsweise unsubstituiert oder tragen ein bis drei Halogenatome und/oder eine Nitrogruppe, einen Cyanorest und/oder einen oder zwei Methyl-, Trifluormethyl-, Methoxy- oder Trifluormethoxysubstituenten. Die erfindungsgemäßen Verbindungen der Formel I mit R9 = Ha werden als Verbindungen der Formel Ia sowie Verbindungen der Formel I mit R9 = Ilb als Ib bezeichnet.All phenyl rings or heterocyclyl radicals and all components in Phenylkompo- phenyl-alkyl, phenylcarbonyl-alkyl, phenylcarbonyl, phenylalkylcarbonyl, Phenylalkenylcarbonyl, phenoxycarbonyl, Phe nyloxythiocarbonyl, Phenylammocarbonyl, N-alkyl-N-phenylaminocarbonyl, phenylsulfonyl and phenoxysulfonyl or all heterocycles lylkomponenten in heterocyclyl-alkyl, heterocyclylcarbonyl-alkyl, heterocyclylcarbonyl, heterocyclylalkylcarbonyl, heterocyclylalkenylcarbonyl, heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl, heterocyclylaminoclyloxy, heterocyclyloxy-nylcynyl, n-alkyl-nyl-heterocyl, up to three halogen atoms and / or a nitro group, a cyano radical and / or one or two methyl, trifluoromethyl, methoxy or trifluoromethoxy substituents. The compounds of the formula I according to the invention with R 9 = Ha are referred to as compounds of the formula Ia and compounds of the formula I with R 9 = Ilb as Ib.
Bevorzugt sind tricyclische Pyrazolonderivate der Formel IIITricyclic pyrazolone derivatives of the formula III are preferred
Figure imgf000029_0001
Figure imgf000029_0001
in der die Substituenten die oben angegebenen Bedeutungen haben.in which the substituents have the meanings given above.
Bevorzugt sind auch tricyclische Pyrazolonderivate der Formel IVTricyclic pyrazolone derivatives of the formula IV are also preferred
Figure imgf000029_0002
Figure imgf000029_0002
in der die Substituenten die oben angegebenen Bedeutungen haben.in which the substituents have the meanings given above.
In Hinblick auf die Verwendung der erfindungsgemäßen Verbindungen der Formeln I, III bzw. IV als Herbizide haben die Variablen vorzugsweise folgende Bedeutungen, und zwar jeweils für sich allein oder in Kombination:With regard to the use of the compounds of the formulas I, III and IV according to the invention as herbicides, the variables preferably have the following meanings, in each case individually or in combination:
R1 Wasserstoff, Cχ-C6 -Alkyl, Cι-C6-Haloalkyl, Ci-Cδ-Alkoxy, Cι-C6-Alkylthio, Cι-C6-Alkylsulfonyl, Halogen, Cyano oder Nitro;R 1 is hydrogen, Cχ-C 6 -alkyl, -C-C 6 -haloalkyl, Ci-C δ -alkoxy, Cι-C 6 -alkylthio, Cι-C 6 -alkylsulfonyl, halogen, cyano or nitro;
R2 Wasserstoff, Cι-C6 -Alkyl, Cι-C6 -Alkoxy, Cι-C6-Halo- alkyl, Ci-Cß-Haloalkoxy, gegebenenfalls mit Cι-C3 -Alkyl, Halogen, Cyano, Nitro oder Ci-C3 -Alkyl- sulfonyl substituiertes Phenyl oder gegebenenfalls mit Cι-C3 -Alkyl, Halogen, Cyano oder Nitro substituiertes Phenylsulfonyl; R3, R4 Wasserstoff, Cι-C6 -Alkyl, Cι-C6 -Alkoxy, Ci -C6 -Alkyl - thio, Cι-C6-Alkylsulfonyl, C2-C6-Alkoxyalkyl, Cι-C6 -Alkoxycarbonyl, Cι-C6-Alkylcarbonyl, Halogen, gegebenenfalls mit Cι-C3 -Alkyl, Halogen, Cyano oder Nitro substituiertes Phenyl;R 2 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkyl, Ci-C ß -haloalkoxy, optionally with C 1 -C 3 -alkyl, halogen, cyano, nitro or Ci -C 3 -alkyl-sulfonyl-substituted phenyl or phenylsulfonyl optionally substituted with -C-C 3 -alkyl, halogen, cyano or nitro; R 3, R 4 are hydrogen, C 6 -alkyl, C 6 alkoxy, Ci-C6 alkyl - thio, Cι-C 6 alkylsulfonyl, C 2 -C 6 alkoxyalkyl, Cι-C 6 - Alkoxycarbonyl, C 1 -C 6 -alkylcarbonyl, halogen, optionally substituted with C 1 -C 3 -alkyl, halogen, cyano or nitro;
R5 Wasserstoff;R5 is hydrogen;
R6 Wasserstoff, Cχ-C3-Alkyl oder Halogen;R6 is hydrogen, Cχ-C 3 alkyl or halogen;
n 1 oder 2.n 1 or 2.
Rio Hydroxy, Mercapto, Halogen, OR13, SR13, SOR14, S02R14,Rio Hydroxy, Mercapto, Halogen, OR 13 , SR 13 , SOR 14 , S0 2 R 14 ,
OS02R14, OP(0)R15R16, OP(S)R15R16- N lRl8, ONR14R14 oder N- gebundenes Heterocyclyl, das 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 Ci -C4-Halogenalkoxy; bevorzugt Hydroxy, Mercapto, Halogen, OR13, SR13, S0R14, OS02R14, NR17R18, ONR1R14 oder N-gebundenes Heterocyclyl, das partiell oder vollständig halogeniert sein kann und/ oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, Cι-C -Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy oder C1-C4-Halogenalkoxy;OS0 2 R 14 , OP (0) R 15 R 16 , OP (S) R 15 R 16 - N 1 R 18 , ONR 14 R 14 or N-linked heterocyclyl, which can be partially or completely halogenated and / or one to can carry three of the following radicals: nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or Ci -C 4 haloalkoxy; preferably hydroxy, mercapto, halogen, OR 13 , SR 13 , S0R 14 , OS0 2 R 14 , NR 17 R 18 , ONR 1 R 14 or N-linked heterocyclyl, which can be partially or completely halogenated and / or one to three of the can carry the following radicals: nitro, cyano, -CC alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy;
R11 Wasserstoff oder C1-C4 -Alkyl, wie Methyl, Ethyl oder Propyl oder 1-Methylethyl; bevorzugt Methyl, Ethyl, Propyl oder 1-Methylethyl; insbesondere bevorzugt Methyl oder Ethyl;R 11 is hydrogen or C 1 -C 4 alkyl, such as methyl, ethyl or propyl or 1-methylethyl; preferably methyl, ethyl, propyl or 1-methylethyl; particularly preferably methyl or ethyl;
Ri Wasserstoff oder C1-C4 -Alkyl, wie Methyl, Ethyl oder Propyl; bevorzugt Wasserstoff oder Methyl; insbesondere bevorzugt Wasserstoff;Ri is hydrogen or C 1 -C 4 alkyl, such as methyl, ethyl or propyl; preferably hydrogen or methyl; particularly preferably hydrogen;
Ri3 Cι-C6-Alkyl, C3-C6 -Alkenyl, C3 -C6 -Halogenalkenyl, R i3 -CC 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl,
C3-C6 -Alkinyl, Ci-Cδ-Alkylcarbonyl, C -C6-Alkenylcarbonyl,C 3 -C 6 alkynyl, Ci-C δ alkylcarbonyl, C -C 6 alkenylcarbonyl,
C3-Cδ -Cycloalkylcarbonyl, Ci -C6 -Alkoxycarbonyl,C 3 -C δ cycloalkylcarbonyl, Ci -C 6 alkoxycarbonyl,
C3- ζ-Alkenyloxycarbonyl, C3 -Ce -Alkinyloxycarbonyl, Ci-Cβ-Alkylthiocarbonyl, Ci-Cβ-Alkylaminocarbonyl,C 3 - ζ-alkenyloxycarbonyl, C 3 -Ce alkynyloxycarbonyl, Ci-Cβ-alkylthiocarbonyl, Ci-Cβ-alkylaminocarbonyl,
C3-Cδ -Alkenylaminocarbonyl, C3-Cδ -Alkinylaminocarbonyl, N,N-Di (Cι-C6 -alkyl) aminocarbonyl, N- (C3-Cδ-Alkenyl) -N- (Ci-Cε-alkyl) -aminocarbonyl, N- (C3-C6-Alkin- yl) -N- (Ci-Cβ-alkyl) -aminocarbonyl, N- (Ci-Cβ-Alk- oxy) -N- (Ci-Cβ-alkyl) -aminocarbonyl, N- (C3-Cδ -Alkenyl) -N- (Cι-C6 -alkoxy) -aminocarbonyl, N- (C3-C6-Alkin- yl) -N- (Cι-C6-alkoxy) -aminocarbonyl, Di- (Ci-Cβ-alk- yl) -aminothiocarbonyl, Cχ-C6-Alkoxyimino-Cι-C6-alkyl, wobei die genannten Alkyl-, Cycloalkyl- oder Alkoxyreste partiell oder vollständig halogeniert sein können und/ oder eine bis drei der folgenden Gruppen tragen können: Cyano, C1-C4-Alkoxy, Cι-C4-Alkylthio, Di- (Cι-C4-alkyl) - amino, Cι-C4-Alkylcarbonyl, C1-C4 -Alkoxycarbonyl, Hydroxy- carbonyl, Cι-C4-Alkylaminocarbonyl, Di- (C1-C4 -Alkyl) aminocarbonyl, Cι-C -Alkylcarbonyloxy oder C3 -C6-Cycloalkyl;C 3 -C δ- alkenylaminocarbonyl, C 3 -C δ -alkynylaminocarbonyl, N, N-di (Cι-C 6 -alkyl) aminocarbonyl, N- (C 3 -C δ- alkenyl) -N- (Ci-Cε- alkyl) -aminocarbonyl, N- (C 3 -C 6 -alkynyl) -N- (Ci-Cβ-alkyl) -aminocarbonyl, N- (Ci-Cβ-alkoxy) -N- (Ci-Cβ- alkyl) -aminocarbonyl, N- (C 3 -C δ- alkenyl) -N- (-C-C 6 -alkoxy) -aminocarbonyl, N- (C 3 -C 6 -alkynyl-yl) -N- (Cι-C 6- alkoxy) -aminocarbonyl, di- (Ci-Cβ-alk- yl) -aminothiocarbonyl, Cχ-C6-alkoxyimino-Cι-C 6 alkyl, where the alkyl, cycloalkyl or alkoxy radicals mentioned can be partially or completely halogenated and / or can carry one to three of the following groups: cyano, C 1 -C 4 -alkoxy, -C-C 4 -alkylthio, di- (-C-C 4 -alkyl) - amino, Cι-C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl, hydroxycarbonyl, Cι-C 4 - Alkylaminocarbonyl, di (C 1 -C 4 alkyl) aminocarbonyl, C 1 -C 4 alkylcarbonyloxy or C 3 -C 6 cycloalkyl;
Phenyl, Phenyl -Cι-C6 -alkyl, Phenylcarbonyl -CI-CÖ -alkyl,Phenyl, phenyl -Cι-C 6 alkyl, phenylcarbonyl -C I -C Ö alkyl,
Phenylcarbonyl, Phenoxycarbony1, Phenoxythiocarbonyl, Phenyl -C2 -C6 -alkenylcarbonyl, Heterocyclyl, Heterocy- clyl-Ci-Cö-alkyl, Heterocyclylcarbonyl -Cι-C6-alkyl, Heterocyclylcarbonyl, Heterocyclyloxycarbonyl, Heterocyclylo- xythiocarbonyl oder Heterocyclyl -Cι-C6-alkenylcarbonyl, wobei der Phenyl- oder der Heterocyclyl -Rest der 14 letztgenannten Substituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, C1-C4 -Alkyl, C1-C4-Halogenalkyl, C1-C4 -Alkoxy oder C1-C4 -Halogenalkoxy;Phenylcarbonyl, Phenoxycarbony1, Phenoxythiocarbonyl, Phenyl -C 2 -C 6 -alkenylcarbonyl, Heterocyclyl, Heterocyclyl-Ci-C ö -alkyl, Heterocyclylcarbonyl -Cι-C 6 -alkyl, Heterocyclylcarbonyl, Heterocyclyloxycarbonyl, Heterocyclylyl- xythocyclylyl- C 6 -alkenylcarbonyl, where the phenyl or the heterocyclyl radical of the 14 latter substituents can be partially or completely halogenated and / or can carry one to three of the following radicals: nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy;
bevorzugt Cι-C6 -Alkyl, C3-C6 -Alkenyl, C3-Cβ -Alkinyl, Cι-C6-Alkylcarbonyl, Cχ-C6 -Alkoxycarbonyl, Ci -C_ -Alkyl- aminocarbonyl oder N,N-Di (Ci-Cδ -alkyl) aminocarbonyl, wo- bei die genannten Alkyl- oder Alkoxyreste partiell oder vollständig halogeniert sein können und/oder eine bis drei der folgenden Gruppen tragen können: Cyano, Cι-C -Alkoxy, Cι-C -Alkylthio oder Ci-C4-Alkoxycarbonyl;preferably Cι-C 6 alkyl, C 3 -C 6 alkenyl, C 3 -Cβ alkynyl, Cι-C 6 alkylcarbonyl, Cχ-C 6 -alkoxycarbonyl, C -C_ alkyl aminocarbonyl or N, N-di (Ci-C δ alkyl) aminocarbonyl, WO at the alkyl or alkoxy radicals to be partially or fully halogenated and / or may carry one to three of the following groups: cyano, C -alkoxy, -alkylthio C or Ci-C 4 alkoxycarbonyl;
Phenyl, Phenyl -Ci-Cδ-alkyl, Phenylcarbonyl -Ci-Cβ-alkyl,Phenyl, phenyl-Ci-Cδ-alkyl, phenylcarbonyl-Ci-Cβ-alkyl,
Phenylcarbonyl, Phenoxycarbonyl, Heterocyclyl, Heterocyclyl-Cι-C6-alkyl, Heterocyclylcarbonyl -Ci-Cß-alkyl, Heterocyclylcarbonyl oder Heterocyclyloxycarbonyl, wobei der Phenyl- oder der Heterocyclyl -Rest der 10 letztgenannten Substituenten partiell oder vollständig halogeniert sein kann oder/oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, C1-C4 -Alkyl, C1-C4 -Halogenalkyl, Cι-C4-Alkoxy oder C1-C4 -Halogenalkoxy;Phenylcarbonyl, phenoxycarbonyl, heterocyclyl, heterocyclyl -C-C 6 alkyl, heterocyclylcarbonyl -Ci-C ß -alkyl, heterocyclylcarbonyl or heterocyclyloxycarbonyl, where the phenyl or heterocyclyl radical of the 10 last-mentioned substituents can be partially or completely or halogenated may carry one to three of the following radicals: nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, Cι-C 4 -alkoxy or C 1 -C 4 -haloalkoxy;
Ci-Cβ -Alkyl, C3-Cδ-Alkenyl oder C3-C6-Cycloalkyl, wobei die drei genannten Reste partiell oder vollständig halogeniert sein können und/oder eine bis drei der folgenden Gruppen tragen können: Cyano, C1-C4 -Alkoxy, Cχ-C4-Alkyl- thio, Cι-C4-Alkylcarbonyl oder C1-C4 -Alkoxycarbonyl; Phenyl, Phenyl -C1-C4 -alkyl, Heterocyclyl oder Heterocyclyl -C1-C4-alkyl, wobei der Phenyl- oder der Heterocy- clylrest der vier letztgenannten Substituenten partiell oder vollstänig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, Cι-C4-Alkyl, C1-C4-Halogenalkyl, Cι-C4-Alkoxy, C1-C4 -Halogenalkoxy oder C1-C4 -Alkoxycarbonyl;Ci-Cβ-alkyl, C 3 -Cδ-alkenyl or C 3 -C6-cycloalkyl, where the three radicals mentioned can be partially or completely halogenated and / or can carry one to three of the following groups: cyano, C 1 -C 4 -Alkoxy, Cχ-C 4 alkyl thio, -CC 4 -alkylcarbonyl or C 1 -C 4 alkoxycarbonyl; Phenyl, phenyl-C 1 -C 4 -alkyl, heterocyclyl or heterocyclyl-C 1 -C 4 -alkyl, where the phenyl or heterocyclic radical of the four last-mentioned substituents can be partially or completely halogenated and / or one to three of the following can carry radicals: nitro, cyano, C 4 alkyl, C 1 -C 4 haloalkyl, Cι-C 4 alkoxy, C 1 -C 4 -haloalkoxy or C 1 -C 4 alkoxycarbonyl;
R15, R16 Hydroxy, Cι-C6-Alkyl, C-x-Cö-Alkoxy, Phenyl, Phe- nyl -C1-C4-alkyl oder Phenoxy, wobei die drei letztgenannten Substituenten partiell oder vollständig halogeniert sein können und/oder einen bis drei der folgenden Reste tragen können: Nitro, Cyano, C1-C4 -Alkyl, C1-C4-Halogenalkyl, C1-C4 -Alkoxy, C1-C4-Halogenalkoxy oder Ci-C4-Alkoxycarbonyl;R 15 , R 16 hydroxy, -CC 6 alkyl, CxC ö alkoxy, phenyl, phenyl -C 1 -C 4 alkyl or phenoxy, where the latter three substituents can be partially or completely halogenated and / or one can carry up to three of the following radicals: nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy or Ci-C 4 alkoxycarbonyl ;
Ri7 Cι-C6-Alkyl, C3-C6-Alkenyl, C3-C6-Halogenalkenyl,Ri 7 Cι-C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl,
C3-C6 -Cycloalkyl, Cχ-C6 -Alkoxy, C3-C6-Alkenyloxy oderC 3 -C 6 cycloalkyl, Cχ-C 6 alkoxy, C 3 -C 6 alkenyloxy or
Di- (Cι-C6 -alkyl) amino, wobei die genannten Alkyl - , Cyclo- alkyl- oder Alkoxyreste partiell oder vollständig halogeniert sein können und/oder einen bis drei der folgenden Reste tragen können: Cyano, C1-C4 -Alkoxycarbonyl, Cι-C4-Alkylaminocarbonyl, Di- (C1-C4-alkyl) aminocarbonyl oder C3-Cβ-Cycloalkyl;Di- (-C 6 -alkyl) amino, where the alkyl, cycloalkyl or alkoxy radicals mentioned can be partially or completely halogenated and / or can carry one to three of the following radicals: cyano, C 1 -C 4 - Alkoxycarbonyl, C 1 -C 4 -alkylaminocarbonyl, di- (C 1 -C 4 -alkyl) aminocarbonyl or C 3 -Cβ-cycloalkyl;
Phenyl, Phenyl -Ci-C -alkyl, Phenylcarbonyl, Heterocyclyl, Heterocycly-Cι-C4-alkyl oder Heterocyclylcarbonyl, wobei der Phenyl- oder Heterocyclyl-Rest der sechs letztgenannten Substituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, C1-C -Alkyl, C1-C4-Halogenalkyl, Cι-C4-Alkoxy oder C -C -Halogenalkoxy,-Phenyl, phenyl-C 1 -C 4 -alkyl, phenylcarbonyl, heterocyclyl, heterocycly-C 1 -C 4 -alkyl or heterocyclylcarbonyl, where the phenyl or heterocyclyl radical of the six latter substituents can be partially or completely halogenated and / or one to three of the can carry the following radicals: nitro, cyano, C 1 -C alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C -C haloalkoxy,
iβ Cι-C6 -Alkyl oder C3-C6-Alkenyl.i β -CC 6 alkyl or C 3 -C 6 alkenyl.
Außerordentlich bevorzugt sind die Verbindungen der Formeln I, III bzw. IV mitThe compounds of the formulas I, III and IV are extraordinarily preferred
R1 Methyl, Ethyl, Halogen, Methoxy, Methylthio, Methyl - sulfonyl, Nitro, Cyano;R 1 is methyl, ethyl, halogen, methoxy, methylthio, methylsulfonyl, nitro, cyano;
R2 Methyl, Ethyl, gegebenenfalls mit Halogen, Cyano,R 2 is methyl, ethyl, optionally with halogen, cyano,
Nitro substituiertes Phenyl oder gegebenenfalls mit Halogen, Cyano, Nitro substituiertes Phenylsulfonyl; R3, R4 Wasserstoff, Ci-Cβ-Alkyl, Ci-Cβ-Alkylcarbonyl, gegebenenfalls durch Halogen, Cyano, Nitro substituiertes Phenyl;Nitro substituted phenyl or phenylsulfonyl optionally substituted with halogen, cyano, nitro; R 3 , R 4 are hydrogen, Ci-Cβ-alkyl, Ci-Cβ-alkylcarbonyl, phenyl optionally substituted by halogen, cyano, nitro;
R5 Wasserstoff;R 5 is hydrogen;
R6 Wasserstoff, Methyl, Chlor;R 6 is hydrogen, methyl, chlorine;
nn
Ebenso außerordentlich bevorzugt sind die Verbindungen der Formel I, III bzw. IV mitThe compounds of the formula I, III or IV are also extremely preferred
Rio Hydroxy;Rio Hydroxy;
Ebenso außerordentlich bevorzugt sind die Verbindungen der Formel I, III bzw. IV mitThe compounds of the formula I, III or IV are also extremely preferred
Ro Halogen, OR-3, SR13, S02R14, OS02R4, NRi7R8, ONRiRi 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, Cι-C -Alkoxy oder Ci -C4 -Halogenalkoxy;Ro halogen, OR- 3 , SR 13 , S0 2 R 14 , OS0 2 R 4 , NRi 7 R 8 , ONRiRi or N-linked heterocyclyl, which can be partially or completely halogenated and / or can carry one to three of the following radicals : Nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or Ci -C 4 haloalkoxy;
Ebenso außerordentlich bevorzugt sind die Verbindungen der Formel I, III bzw. IV mitThe compounds of the formula I, III or IV are also extremely preferred
RU Cx-C4-Alkyl;RU C x -C 4 alkyl;
R2 Wasserstoff oder C1-C4 -Alkyl;R 2 is hydrogen or C 1 -C 4 alkyl;
Außerordentlichst bevorzugt sind die Verbindungen der Formel I, III bzw. IV mit R6=H, R10=OH und n=l, insbesondere die Verbindungen III 1 bis III 11 und IV 1 bis IV 11, wobei dieExtremely preferred are the compounds of the formula I, III or IV with R 6 = H, R 10 = OH and n = 1, in particular the compounds III 1 to III 11 and IV 1 to IV 11, where the
Restedefinitionen Ri bis Ri8, X, 1 und n nicht nur in Kombination miteinander, sondern auch jeweils für sich alleine betrachtet für die erfindungsgemäßen Verbindungen eine besondere Bedeutung haben. Tabelle AResidual definitions R i to R i8 , X, 1 and n not only have a special meaning for the compounds according to the invention, not only in combination with one another, but also in isolation. Table A
Figure imgf000034_0001
Figure imgf000035_0001
Figure imgf000034_0001
Figure imgf000035_0001
Tabelle 1: Verbindungen III 1.1 - III 1.60Table 1: Compounds III 1.1 - III 1.60
Figure imgf000036_0001
Figure imgf000036_0001
Verbindungen der allgemeinen Formel III 1, in der die Substituenten R1, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle A entsprechen.Compounds of the general formula III 1 in which the substituents R 1 , R 3 and R 6 correspond to one row of Table A for each individual compound.
Tabelle 2: Verbindungen III 2.1 - III 2.60Table 2: Compounds III 2.1 - III 2.60
Figure imgf000036_0002
Figure imgf000036_0002
Verbindungen der allgemeinen Formel III 2, in der die Substituenten R1, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle A entsprechen.Compounds of the general formula III 2 in which the substituents R 1 , R 3 and R 6 correspond to one row of Table A for each individual compound.
Tabelle 3: Verbindungen III 3.1 - III 3.60Table 3: Compounds III 3.1 - III 3.60
Figure imgf000036_0003
Figure imgf000036_0003
Verbindungen der allgemeinen Formel III 3, in der die Substituenten R1, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle A entsprechen. Tabelle 4: Verbindungen III 4.1 - III 4.60Compounds of the general formula III 3 in which the substituents R 1 , R 3 and R 6 correspond to one row of Table A for each individual compound. Table 4: Compounds III 4.1 - III 4.60
Figure imgf000037_0001
Figure imgf000037_0001
Verbindungen der allgemeinen Formel III 4, in der die Substituenten R1, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle A entsprechen.Compounds of the general formula III 4, in which the substituents R 1 , R 3 and R 6 correspond to one row of Table A for each individual compound.
Tabelle 5: Verbindungen III 5.1 - III 5.60Table 5: Compounds III 5.1 - III 5.60
Figure imgf000037_0002
Figure imgf000037_0002
Verbindungen der allgemeinen Formel III 5, in der die Substituenten R1, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle A entsprechen.Compounds of the general formula III 5, in which the substituents R 1 , R 3 and R 6 correspond to one row of Table A for each individual compound.
Tabelle 6: Verbindungen III 6.1 - III 6.60Table 6: Compounds III 6.1 - III 6.60
Figure imgf000037_0003
Figure imgf000037_0003
Verbindungen der allgemeinen Formel III 6, in der die Substituenten R1, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle A entsprechen. Tabelle 7: Verbindungen III 7.1 - III 7.60Compounds of the general formula III 6, in which the substituents R 1 , R 3 and R 6 correspond to one row of Table A for each individual compound. Table 7: Compounds III 7.1 - III 7.60
Figure imgf000038_0001
Figure imgf000038_0001
Verbindungen der allgemeinen Formel III 7, in der die Substituenten R1, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle A entsprechen.Compounds of the general formula III 7, in which the substituents R 1 , R 3 and R 6 correspond to one row of Table A for each individual compound.
Tabelle 8: Verbindungen III 8.1 - III 8.60Table 8: Compounds III 8.1 - III 8.60
Figure imgf000038_0002
Figure imgf000038_0002
Verbindungen der allgemeinen Formel III 8, in der die Substituenten R1, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle A entsprechen.Compounds of the general formula III 8, in which the substituents R 1 , R 3 and R 6 correspond to one row of Table A for each individual compound.
Tabelle 9: Verbindungen III 9.1 - III 9.60Table 9: Compounds III 9.1 - III 9.60
Figure imgf000038_0003
Figure imgf000038_0003
Verbindungen der allgemeinen Formel III 9, in der die Substituenten R1, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle A entsprechen. Tabelle 10: Verbindungen III 10.1 - III 10.60Compounds of the general formula III 9, in which the substituents R 1 , R 3 and R 6 correspond to one row of Table A for each individual compound. Table 10: Compounds III 10.1 - III 10.60
Figure imgf000039_0001
Figure imgf000039_0001
Verbindungen der allgemeinen Formel III 10, in der die Substituenten R1, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle A entsprechen.Compounds of the general formula III 10, in which the substituents R 1 , R 3 and R 6 correspond to one row of Table A for each individual compound.
Tabelle 11: Verbindungen III 11.1 - III 11.60Table 11: Compounds III 11.1 - III 11.60
Figure imgf000039_0002
Figure imgf000039_0002
Verbindungen der allgemeinen Formel III 11, in der die Substituenten R1, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle A entsprechen. Compounds of the general formula III 11, in which the substituents R 1 , R 3 and R 6 correspond to one row of Table A for each individual compound.
Tabelle BTable B
Figure imgf000040_0001
Figure imgf000041_0001
Figure imgf000042_0001
Figure imgf000043_0001
Figure imgf000044_0001
Figure imgf000045_0001
Figure imgf000046_0001
Figure imgf000047_0001
Tabelle 12: Verbindungen IV 1.1 - IV 1.300
Figure imgf000040_0001
Figure imgf000041_0001
Figure imgf000042_0001
Figure imgf000043_0001
Figure imgf000044_0001
Figure imgf000045_0001
Figure imgf000046_0001
Figure imgf000047_0001
Table 12: Compounds IV 1.1 - IV 1.300
Figure imgf000048_0001
Figure imgf000048_0001
Verbindungen der allgemeinen Formel IV 1, in der die Substituenten Ri, R2, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle B entsprechen.Compounds of the general formula IV 1, in which the substituents R i , R 2 , R 3 and R 6 correspond to one row of Table B for each individual compound.
Tabelle 13: Verbindungen IV 2.1 - IV 2.300Table 13: Compounds IV 2.1 - IV 2.300
Figure imgf000048_0002
Figure imgf000048_0002
Verbindungen der allgemeinen Formel IV 2, in der die Substituenten R1, R2, R3 und R6 für jede einzelne Verbindung je- weils einer Zeile der Tabelle B entsprechen.Compounds of the general formula IV 2, in which the substituents R 1 , R 2 , R 3 and R 6 correspond to one row of Table B for each individual compound.
Tabelle 14: Verbindungen IV 3.1 - IV 3.300Table 14: Compounds IV 3.1 - IV 3.300
Figure imgf000048_0003
Figure imgf000048_0003
Verbindungen der allgemeinen Formel IV 3, in der die Substituenten R1, R2, R3 und R6 für jede einzelne Verbindung je- weils einer Zeile der Tabelle B entsprechen. Tabelle 15: Verbindungen IV 4.1 - IV 4.300Compounds of the general formula IV 3 in which the substituents R 1 , R 2 , R 3 and R 6 correspond to one row of Table B for each individual compound. Table 15: Compounds IV 4.1 - IV 4.300
Figure imgf000049_0001
Figure imgf000049_0001
Verbindungen der allgemeinen Formel IV 4, in der die Substituenten R , R2, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle B entsprechen.Compounds of the general formula IV 4, in which the substituents R, R 2 , R 3 and R 6 correspond to one row of Table B for each individual compound.
Tabelle 16: Verbindungen IV 5.1 - IV 5.300Table 16: Compounds IV 5.1 - IV 5.300
Figure imgf000049_0002
Figure imgf000049_0002
Verbindungen der allgemeinen Formel IV 5, in der die Substituenten R1, R2, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle B entsprechen.Compounds of the general formula IV 5 in which the substituents R 1 , R 2 , R 3 and R 6 correspond to one row of Table B for each individual compound.
Tabelle 17: Verbindungen IV 6.1 - IV 6.300Table 17: Compounds IV 6.1 - IV 6.300
Figure imgf000049_0003
Figure imgf000049_0003
Verbindungen der allgemeinen Formel IV 6, in der die Substituenten R1, R2, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle B entsprechen. Tabelle 18 : Verbindungen IV 7 . 1 - IV 7 . 300Compounds of the general formula IV 6, in which the substituents R 1 , R 2 , R 3 and R 6 correspond to one row of Table B for each individual compound. Table 18: Compounds IV 7. 1 - IV 7. 300
Figure imgf000050_0001
Figure imgf000050_0001
Verbindungen der allgemeinen Formel IV 7 , in der die Substituenten R1, R2, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle B entsprechen.Compounds of the general formula IV 7, in which the substituents R 1 , R 2 , R 3 and R 6 correspond to one row of Table B for each individual compound.
Tabelle 19: Verbindungen IV 8.1 - IV 8.300Table 19: Compounds IV 8.1 - IV 8.300
Figure imgf000050_0002
Figure imgf000050_0002
Verbindungen der allgemeinen Formel IV 8, in der die Substituenten R1, R2, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle B entsprechen.Compounds of the general formula IV 8, in which the substituents R 1 , R 2 , R 3 and R 6 correspond to one row of Table B for each individual compound.
Tabelle 20: Verbindungen IV 9.1 - IV 9.300Table 20: Compounds IV 9.1 - IV 9.300
Figure imgf000050_0003
Figure imgf000050_0003
Verbindungen der allgemeinen Formel IV 9, in der die Substituenten R1, R2, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle B entsprechen. Tabelle 21: Verbindungen IV 10.1 - IV 10.300Compounds of the general formula IV 9, in which the substituents R 1 , R 2 , R 3 and R 6 correspond to one row of Table B for each individual compound. Table 21: Compounds IV 10.1 - IV 10.300
Figure imgf000051_0001
Figure imgf000051_0001
Verbindungen der allgemeinen Formel IV 10, in der die Substituenten R1, R2, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle B entsprechen.Compounds of the general formula IV 10, in which the substituents R 1 , R 2 , R 3 and R 6 correspond to one row of Table B for each individual compound.
Tabelle 22: Verbindungen IV 11.1 - IV 11.300Table 22: Compounds IV 11.1 - IV 11.300
Figure imgf000051_0002
Figure imgf000051_0002
Verbindungen der allgemeinen Formel IV 11, in der die Substituenten R1, R2, R3 und R6 für jede einzelne Verbindung jeweils einer Zeile der Tabelle B entsprechen. Compounds of the general formula IV 11 in which the substituents R 1 , R 2 , R 3 and R 6 correspond to one row of Table B for each individual compound.
Darstellung von Verbindungen der Formel I mit R10=Hydroxy durch Umsetzung einer aktivierten Carbonsäure Va oder einer Carbonsäure Vb, die vorzugsweise in situ aktiviert wird, mit einem Pyrazolon der Formel XII zu einem Acylierungsprodukt und anschließende Umlagerung.Preparation of compounds of the formula I with R 10 = hydroxy by reacting an activated carboxylic acid Va or a carboxylic acid Vb, which is preferably activated in situ, with a pyrazolone of the formula XII to give an acylation product and subsequent rearrangement.
Figure imgf000052_0001
Figure imgf000052_0001
Figure imgf000052_0002
Figure imgf000052_0002
I (mit Rl° = OH) wobei die Reste Ri-Ri8, X, 1 und n die oben angegebene Bedeutung haben und h1 für eine nucleophil verdrängbare Abgangs- gruppe, wie Halogen z.B. Brom oder Chlor, Hetaryl, z.B. Imidazolyl oder Pyridyl, Carboxylat, z.B. Acetat oder Tri- fluoracetat etc. steht.I (with Rl ° = OH) where the radicals R i -R i8 , X, 1 and n have the meaning given above and h 1 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 tri - fluoroacetate etc.
Die aktivierte Benzoesäure Va kann direkt eingesetzt werden, wie im Fall der Benzoylhalogenide oder in situ erzeugt werden, z.B. mit Dicyclohexylcarbodiimid, Triphenylphosphin/Azo- dicarbonsäureester, 2-Pyridindisulfid/Triphenylphosphin, Carbonyldiimidazol etc.The activated benzoic acid Va can be used directly, as in the case of the benzoyl halides, or generated in situ, e.g. with dicyclohexylcarbodiimide, triphenylphosphine / azodicarboxylic acid ester, 2-pyridine disulfide / triphenylphosphine, carbonyldiimidazole etc.
Gegebenenfalls kann es von Vorteil sein, die Acylierungsreak- tion in Gegenwart einer Base auszuführen. Die Reaktanden und die Hilfsbase werden dabei zweckmäßigerweise in äquimolaren Mengen eingesetzt. Ein geringer Überschuß der Hilfsbase z.B. 1,2 bis 1,5 Moläquivalente, bezogen auf Va bzw. Vb, kann unter Umständen vorteilhaft sein.It may be advantageous to carry out the acylation reaction in the presence of a base. The reactants and the auxiliary base are expediently used in equimolar amounts. A slight excess of the auxiliary base e.g. Under certain circumstances, 1.2 to 1.5 molar equivalents, based on Va or Vb, can be advantageous.
Als Hilfsbasen eignen sich tertiäre 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, Tetrahydrofuran oder Dioxan, polare aprotische Lösungsmittel, wie Acetonitril, Dimethylformamid oder Dimethylsulfoxid oder Ester wie Essigsäureethylester oder Gemische hiervon verwendet werden.Tertiary alkyl amines, pyridine or alkali metal carbonates are suitable as auxiliary bases. As a solvent e.g. chlorinated hydrocarbons such as methylene chloride or 1, 2-dichloroethane, aromatic hydrocarbons such as toluene, xylene or chlorobenzene, ethers such as diethyl ether, methyl tert-butyl ether, tetrahydrofuran or dioxane, polar aprotic solvents such as acetonitrile, dimethylformamide or dimethyl sulfoxide or ester such as ethyl acetate or mixtures thereof.
Werden Benzoylhalogenide als aktivierte Carbons urekomponente 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 Aufarbei- tung erfolgt in üblicher Weise, z.B. wird das Reaktionsgemisch auf Wasser gegossen, das Wertprodukt extrahiert. Als Lösungsmittel eignen sich hierfür besonders Methylenchlorid, Diethylether und Essigsäureethylester. Nach Trocknen der organischen Phase und Entfernen des Lösungsmittels kann der rohe Ester ohne weitere Reinigung zur Ümlagerung eingesetzt werden.If benzoyl halides are used as the activated carboxylic acid component, it may be expedient to cool the reaction mixture to 0-10 ° C. when this reactant is added. The mixture is then stirred at 20-100 ° C., preferably at 25-50 ° C., until the reaction is complete. The processing takes place in the usual way, e.g. the reaction mixture is poured onto water and the product of value is extracted. Methylene chloride, diethyl ether and ethyl acetate are particularly suitable as solvents for this. After drying the organic phase and removing the solvent, the crude ester can be used for the rearrangement without further purification.
Die ümlagerung der Ester zu den Verbindungen der Formel I erfolgt zweckmäßigerweise bei Temperaturen von 20 bis 100°C in einem Lösungsmittel und in Gegenwart einer Base sowie gegebenenfalls mit Hilfe einer Cyanoverbindung als Katalysator. Als Lösungsmittel können z.B. Acetonitril, Methylenchlorid, 1, 2-Dichlorethan, Dioxan, Essigsäureethylester, Toluol oder Gemische hiervon verwendet werden. Bevorzugte Lösungsmittel sind Acetonitril und Dioxan. 5The rearrangement of the esters to the compounds of the formula I is advantageously carried out at from 20 to 100 ° C. in a solvent and in the presence of a base and, if appropriate, using a cyano compound as a catalyst. For example, acetonitrile, methylene chloride, 1, 2-dichloroethane, dioxane, ethyl acetate, toluene or mixtures thereof can be used as solvents. Preferred solvents are acetonitrile and dioxane. 5
Geeignete Basen sind tertiäre Amine wie Triethylamin, aromatische Amine wie Pyridin oder Alkalicarbonate, wie Natrium- carbonat oder Kaliumcarbonat, die vorzugsweise in äquimolarer Menge oder bis zu einem vierfachen Überschuß, bezogen auf den 10 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 10 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 15 Natriumcyanid oder Kaliumcyanid und organische Cyanoverbindungen, wie Acetoncyanhydrin oder Trimethylsilylcyanid in Betracht. Sie werden in einer Menge von 1 bis 50 Molprozent, bezogen auf den Ester, eingesetzt. Vorzugsweise werden Acetoncyanhydrin oder Trimethylsilylcyanid, z.B. in einer 20 Menge von 5 bis 15, vorzugsweise etwa 10 Molprozent, bezogen auf den Ester, eingesetzt.Suitable cyano compounds are inorganic cyanides, such as sodium cyanide or potassium cyanide, and organic cyano compounds, such as acetone cyanohydrin or trimethylsilyl cyanide. They are used in an amount of 1 to 50 mole percent, based on the ester. Preferably acetone cyanohydrin or trimethylsilyl cyanide, e.g. in an amount of 5 to 15, preferably about 10 mol percent, based on the ester.
Die Aufarbeitung kann in an sich bekannter Weise erfolgen. Das Reaktionsgemisch wird z.B. mit verdünnter Mineralsäure,Working up can be carried out in a manner known per se. The reaction mixture is e.g. with dilute mineral acid,
25 wie 5 %ige Salzsäure oder Schwefelsäure, angesäuert, mit einem organischen Lösungsmittel, z.B. Methylenchlorid oder Essigsäureethylester extrahiert. Der organische Extrakt kann mit 5-10%iger Alkalicarbonatlösung, z.B. Natriumcarbonat- oder Kaliumcarbonatlösung extrahiert werden. Die wäßrige25 such as 5% hydrochloric acid or sulfuric acid, acidified with an organic solvent, e.g. Extracted methylene chloride or ethyl acetate. The organic extract can be mixed with 5-10% alkali carbonate solution, e.g. Sodium carbonate or potassium carbonate solution can be extracted. The watery
30 Phase wird angesäuert und der sich bildende Niederschlag abgesaugt und/oder mit Methylenchlorid oder Essigsäureethylester extrahiert, getrocknet und eingeengt.30 phase is acidified and the precipitate formed is suction filtered and / or extracted with methylene chloride or ethyl acetate, dried and concentrated.
B. Darstellung von Verbindungen der Formel I mit R10 = Halogen 35 durch Umsetzung von tricyclischen Pyrazolonderivaten der Formel I (mit Ri° = Hydroxy) mit Halogenierungsmitteln:B. Preparation of Compounds of Formula I with R 10 = Halogen 35 by Reaction of Tricyclic Pyrazolone Derivatives of Formula I (with R i ° = Hydroxy) with Halogenating Agents:
4 *0 u I iaa uunndd//ooddeerr I ibb (mit Rl 0 = HalQ a gPen))4 * 0 u I iaa uundndd // ooddeerr I ibb (with Rl 0 = HalQ a g P en))
Figure imgf000054_0001
Figure imgf000054_0001
45 I (mit Rl° = OH) Als Halogenierungsmittel eignen sich beispielsweise Phosgen, Diphosgen, Triphosgen, Thionylchlorid, Oxalylchlorid, Phosphoroxychlorid, Phosphorpentachlorid, Mesylchlorid, Chlormethylen-N,N-dimethylammoniumchlorid, Oxalylbromid, Phosphoroxybromid etc.45 I (with R l ° = OH) Suitable halogenating agents are, for example, phosgene, diphosgene, triphosgene, thionyl chloride, oxalyl chloride, phosphorus oxychloride, phosphorus pentachloride, mesyl chloride, chloromethylene-N, N-dimethylammonium chloride, oxalyl bromide, phosphorus oxybromide etc.
Darstellung von Verbindungen der Formel I mit Ri0 = OR23, OS02R14, OPORi5Ri6 oder OPSRi5R6 durch Umsetzung von tricyclischen Pyrazolonderivaten der Formel I (mit R10 = Hydroxy) mit Alkylierungs- , Sulfonylierungs- bzw. Phosphonylierungsmitteln Preparation of compounds of the formula I with R i0 = OR 23 , OS0 2 R 14 , OPOR i5 R i6 or OPSR i5 R 6 by reacting tricyclic pyrazolone derivatives of the formula I (with R 10 = hydroxy) with alkylation, sulfonylation or Phosphonylating agents
Ri6 R i6
Figure imgf000055_0001
Figure imgf000055_0001
L2 - pSR15R16 Aδ L 2 - p SR 15 R 16 Aδ
L2 steht für eine nucleophil verdrängbare Abgangsgruppe, wie Halogen, z. B. Chlor oder Brom, Hetaryl, z. B. Imidazolyl, Carboxylat, z. B. Acetat, oder Sulfonat, z. B. Mesylat oder Triflat etc.L 2 stands for a nucleophilically displaceable leaving group, such as halogen, for. B. chlorine or bromine, hetaryl, e.g. B. imidazolyl, carboxylate, e.g. B. acetate, or sulfonate, e.g. B. mesylate or triflate etc.
Die Verbindungen der Formel Aα, Aß, Aγ oder Aδ können direkt eingesetzt werden wie z. B. im Fall der Carbonsäurehalogenide oder in situ erzeugt werden, z. B. aktivierte Carbonsäuren (mit Carbonsäure und Dicyclohexylcarbodiimid etc.).The compounds of formula Aα, Aß, Aγ or Aδ can be used directly, such as. B. in the case of carboxylic acid halides or generated in situ, for. B. activated carboxylic acids (with carboxylic acid and dicyclohexylcarbodiimide etc.).
Darstellung von Verbindungen der Formel I mit R10 = ORi3, SR13, PORi5R16, NRi7Ri8, ONRi4Ri4 oder N-gebundenes Heterocyclyl durch Umsetzung von Verbindungen der Formel I mit Ri0 = Halogen, OSO2R14 mit Verbindungen der Formel Bα, Bß, Bγ, Bδ, Bε oder Bη, gegebenenfalls in Gegenwart einer Base oder unter voran- gehender Salzbildung. HORl*3 Bα oder Ia und/oder Ib (mitPreparation of compounds of the formula I with R 10 = OR i3 , SR 13 , POR i5 R 16 , NR i7 R i8 , ONR i4 R i4 or N-linked heterocyclyl by reacting compounds of the formula I with R i0 = halogen, OSO 2 R 14 with compounds of the formula Bα, Bß, Bγ, Bδ, Bε or Bη, optionally in the presence of a base or with previous salt formation. HORl * 3 Bα or Ia and / or Ib (with
Ia und/oder Ib Ro = ORi-3, SRI*3, (mit Ri° = Halogen, ^ HSRl*3 PORlSRl6, NR7Rl8, OS02R14 ) oder ONRi4Ri oder N-gebundenesIa and / or Ib Ro = OR i - 3 , SR I * 3 , (with R i ° = halogen, ^ HSR l * 3 POR lS R l6 , NR 7 R l8 , OS0 2 R 14 ) or ONR i4 R i or N-linked
HPOR15Rl6 Bγ Heterocyclyl) oderHPOR 15 R 16 Bγ heterocyclyl) or
HNRl7Rl8 Bδ oderHNR l7 R l8 Bδ or
HONRl R14 Bε oderHONR l R 14 Bε or
H (N-gebundenes Bη Heterocyclyl)H (N-linked Bη heterocyclyl)
Darstellung von Verbindungen der Formel I mit Ri0 = SOR14, S02R14 durch Umsetzung von Verbindungen der Formel I mit Ro = SRi4 mit einem Oxidationsmittel.Representation of compounds of formula I with R i0 = SOR 14 , S0 2 R 14 by reacting compounds of formula I with Ro = SR i4 with an oxidizing agent.
Ia und/oder Ib Oxidationsmittel Ia und/oder Ib (mit o = SRi4) (mit Rl° = SORI4, S02Ri4)Ia and / or Ib oxidizing agent Ia and / or Ib (with o = SR i4 ) (with R l ° = SOR I4 , S0 2 R i4 )
Als Oxidationsmittel kommen beispielsweise m-Chlorperbenzoe- säure, Peroxyessigsäure, Trifluorperoxyessigsäure, Wasserstoffperoxid, ggf. in Gegenwart eines Katalysators wie Wol- framat, in Betracht.Examples of suitable oxidizing agents are m-chloroperbenzoic acid, peroxyacetic acid, trifluoroperoxyacetic acid, hydrogen peroxide, if appropriate in the presence of a catalyst such as tungstate.
Die Herstellung der Verbindungen der Formel V erfolgt durch Oxi- dation der Verbindungen der Formel XIII mit Oxidationsmitteln:The compounds of the formula V are prepared by oxidation of the compounds of the formula XIII using oxidizing agents:
Figure imgf000056_0001
wobei T C1-C4 -Alkoxy bedeutet und die übrigen Substituenten die oben beschriebene Bedeutung haben.
Figure imgf000056_0001
where TC 1 -C 4 alkoxy and the other substituents have the meaning described above.
Als Oxidationsmittel eignen sich bspw. m-Chlorperbenzoesäure, Peroxyessigsäure oder Wasserstoffperoxid, ggf. in Gegenwart eines Katalysators wie Wolframat. Die Darstellung von Verbindungen der Formel Xllla erfolgt durch dipolare Cycloaddition von Verbindungen der Formel XIV in Gegenwart eines Oxidationsmittels (s. z.B. Kim, J.N. et.al. Synth. Commun. 1990, 20, 1373; Hassner, A. et. al. Synthesis 1989, 57; Kellabennani, A.E. et. al . Tetrahedron 1995, 51, 10923),Suitable oxidizing agents are, for example, m-chloroperbenzoic acid, peroxyacetic acid or hydrogen peroxide, if appropriate in the presence of a catalyst such as tungsten. Compounds of the formula Xllla are prepared by dipolar cycloaddition of compounds of the formula XIV in the presence of an oxidizing agent (see, for example, Kim, JN et.al. Synth. Commun. 1990, 20, 1373; Hassner, A. et. Al. Synthesis 1989, 57; Kellabennani, AE et al. Tetrahedron 1995, 51, 10923),
Figure imgf000057_0001
XIV Xllla
Figure imgf000057_0001
XIV Xllla
wobei T C1-C4 -Alkoxy bedeutet und die übrigen Substituenten die oben beschriebenen Bedeutungen haben.wherein T is C1-C 4 alkoxy and the remaining substituents have the meanings described above.
Als Oxidationsmittel kommen z.B. Chloramin T oder Natriumhypo- chlorit zur Anwendung.As oxidizing agents come e.g. Chloramine T or sodium hypochlorite are used.
Die Darstellung von Verbindungen der Formel Xlllb erfolgt durch Cycloaddition von Verbindungen der Formel XV (s. z.B. Bishop, J.E. et. al. J. Chem. Soc. Perk. Trans. 1, 1995, 2551; Shimizu, T. et. al. Bull, Chem. Soc. Jpn. 1980, 53, 429; Grigg, R. et. al. Tetrahedron 1987, 43, 5873),Compounds of the formula X11b are prepared by cycloaddition of compounds of the formula XV (see, for example, Bishop, JE et. Al. J. Chem. Soc. Perk. Trans. 1, 1995, 2551; Shimizu, T. et. Al. Bull, Chem. Soc. Jpn. 1980, 53, 429; Grigg, R. et. Al. Tetrahedron 1987, 43, 5873),
Figure imgf000057_0002
Figure imgf000057_0002
worin T C1-C4 -Alkoxy bedeutet und die übrigen Substituenten die oben beschriebene Bedeutung haben.wherein TC 1 -C 4 alkoxy and the other substituents have the meaning described above.
Die Darstellung der Oxime XIV erfolgt nach allgemein bekannten Methoden aus den Aldehyden XVI (s. March, J. Advanced Organic Chemistry, 4. Ed., Wiley and Sons 1992, S. 906 ff.).
Figure imgf000058_0001
The oximes XIV are prepared using generally known methods from the aldehydes XVI (see March, J. Advanced Organic Chemistry, 4th Ed., Wiley and Sons 1992, pp. 906 ff.).
Figure imgf000058_0001
worin T C1-C4 -Alkoxy bedeutet und die übrigen Substituenten die oben beschriebene Bedeutung haben.wherein TC 1 -C 4 alkoxy and the other substituents have the meaning described above.
Die Darstellung der Hydrazone XV erfolgt nach allgemein bekannten Methoden aus den Aldehyden XVI (s. March, J. Advanced Organic Chemistry, 4. Ed., Wiley, 1992, S. 904 ff.).The hydrazone XV is represented by generally known methods from the aldehydes XVI (see March, J. Advanced Organic Chemistry, 4th Ed., Wiley, 1992, pp. 904 ff.).
Figure imgf000058_0002
Figure imgf000058_0002
worin T C1-C4 -Alkoxy bedeutet und die übrigen Substituenten die oben beschriebene Bedeutung haben.wherein TC 1 -C 4 alkoxy and the other substituents have the meaning described above.
Die Darstellung von Verbindungen der Formel XVI erfolgt durch nu- kleophile aromatische Substitution von Verbindungen der Formel XVII mit substituierten Allylthiolen in polaren Lösungsmitteln in Gegenwart von Basen. Als Base können tertiäre Amine wie Triethylamin oder Pyridin oder Alkalimetallcarbonate wie Lithiumcarbonat oder Natriumcarbonat eingesetzt werden.
Figure imgf000059_0001
Compounds of the formula XVI are prepared by nucleophilic aromatic substitution of compounds of the formula XVII with substituted allyl thiols in polar solvents in the presence of bases. Tertiary amines such as triethylamine or pyridine or alkali metal carbonates such as lithium carbonate or sodium carbonate can be used as the base.
Figure imgf000059_0001
Als Lösungsmittel eignen sich Methanol, Ethanol, Dimethylformamid oder N-Methyl-pyrrolidon.Methanol, ethanol, dimethylformamide or N-methyl-pyrrolidone are suitable as solvents.
Die Aldehyde der Formel XVII sind bekannt aus beispielsweise der WO 98/31681. The aldehydes of the formula XVII are known from, for example, WO 98/31681.
Herstellung der AusgangsstoffeProduction of raw materials
a) Synthese von 2-Chlor-3-formyl-4 -allylthio-benzoesäure- methylestera) Synthesis of 2-chloro-3-formyl-4 -allylthio-benzoic acid methyl ester
Zu einer Lösung aus Li2C03 (8,8 g, 119 mmol) undTo a solution of Li 2 CO 3 (8.8 g, 119 mmol) and
2 -Chlor - 3 - formyl - 4 -methylsulfonyl -benzoesäuremethylester2-Chloro-3-formyl-4-methylsulfonyl-benzoic acid methyl ester
(30 g, 108,5 mmol) in EtOH (300 ml) wird Allylthiol (11,5 g, 108,5 mmol) getropft und das Gemisch 12 h unter Rückfluß erhitzt. Man engt am Rotationsverdampfer ein, nimmt den Rückstand in Wasser/Ethylacetat auf, wäscht die organische Phase mit Wasser, trocknet über a2Sθ4 und entfernt das Lösungsmittel. Der braune Rückstand wird an Kieselgel mit Cyclohexan/Ethylacetat (4 : 1) als Eluent chromatografiert .(30 g, 108.5 mmol) in EtOH (300 ml), allyl thiol (11.5 g, 108.5 mmol) is added dropwise and the mixture is heated under reflux for 12 h. It is concentrated on a rotary evaporator, the residue is taken up in water / ethyl acetate, the organic phase is washed with water, dried over a 2 SO 4 and the solvent is removed. The brown residue is chromatographed on silica gel with cyclohexane / ethyl acetate (4: 1) as the eluent.
Ausbeute: 16,8 g (57 %) gelbes ÖlYield: 16.8 g (57%) yellow oil
HNMR δ 10,7 (s, 1H) , 7,86 (d, 1H) , 7,30 (d, 1H) ,HNMR δ 10.7 (s, 1H), 7.86 (d, 1H), 7.30 (d, 1H),
5,90 (m, 1H) , 5,33 (m, 2H) , 3,95 (s, 3H) , 3,63 (d, 2H) .5.90 (m, 1H), 5.33 (m, 2H), 3.95 (s, 3H), 3.63 (d, 2H).
b) Synthese von 2-Chlor-3-hydroxyiminomethyl-4-allylthio- benzoesäuremethylesterb) Synthesis of 2-chloro-3-hydroxyiminomethyl-4-allylthio-benzoic acid methyl ester
Zu einer Lösung aus 2-Chlor-3-formyl-4-allylthio-benzoe- säuremethylester (15,85 g, 58,6 mmol) und Na2C03 (3,5 g, 33 mmol) in Ethanol (200 ml) wird Hydroxylammoniumchlorid (4,48 g, 64,5 mmol) zugesetzt und der Ansatz übers Wo- chenende bei RT gerührt. Man gibt Wasser (200 ml) zu und rührt eine weitere Stunde bevor das Gemisch am Rotations- verdampfer eingeengt wird. Der Rückstand wird in Wasser/ Ethylacetat aufgenommen, die organische Phase über Na2S04 getrocknet und das Lösungsmittel entfernt. Man erhält das Oxim quantitativ als hellen Sirup.To a solution of 2-chloro-3-formyl-4-allylthio-benzoic acid methyl ester (15.85 g, 58.6 mmol) and Na 2 CO 3 (3.5 g, 33 mmol) in ethanol (200 ml) hydroxylammonium chloride (4.48 g, 64.5 mmol) is added and the mixture is stirred at RT over the weekend. Water (200 ml) is added and the mixture is stirred for a further hour before the mixture is concentrated on a rotary evaporator. The residue is taken up in water / ethyl acetate, the organic phase is dried over Na 2 S0 4 and the solvent is removed. The oxime is obtained quantitatively as a light syrup.
IHNMR δ 8,51 (s, 1H) , 8,39 (s, 1H) , 7,73 (d, 1H) , 7,28 (s, 1H), 5,88 (m, 1H) , 5,25 (m, 2H) , 3,93 (s, 3H) , 3,60 I HNMR δ 8.51 (s, 1H), 8.39 (s, 1H), 7.73 (d, 1H), 7.28 (s, 1H), 5.88 (m, 1H), 5, 25 (m, 2H), 3.93 (s, 3H), 3.60
(d, 2H) . Herstellung der Zwischenprodukte(d, 2H). Manufacture of intermediates
c) Synthese von 9-Chlor-4H- thiochromano [4, 3 -c] isoxazolin-8- carbonsäuremethylesterc) Synthesis of 9-chloro-4H-thiochromano [4, 3-c] isoxazoline-8-carboxylic acid methyl ester
Zu einer Lösung der Verbindung 2-Chlor-3-hydroxyimino- methyl-4-allylthiobenzoesäuremethylester (16,3 g, 57 mmol) und einer Spatelspitze NaOAc in CH2C12 (300 ml) wird eine wäßrige NaOCl-Lsg. (12,5 %, 40,8 g, 68,4 mmol) getropft und der Ansatz 6 h unter Rückfluß erhitzt. Nach dem Erkalten trennt man die organische Phase ab, wäscht mit Wasser, trocknet über Na2SÜ4 und entfernt das Lösungsmittel. Die säulenchromatografische Reinigung des Rückstandes liefert das Produkt in Form farbloser Kri- stalle.To a solution of the compound 2-chloro-3-hydroxyimino-methyl-4-allylthiobenzoic acid methyl ester (16.3 g, 57 mmol) and a spatula tip of NaOAc in CH 2 C1 2 (300 ml), an aqueous NaOCl solution. (12.5%, 40.8 g, 68.4 mmol) were added dropwise and the mixture was heated under reflux for 6 h. After cooling, the organic phase is separated off, washed with water, dried over Na 2 SÜ 4 and the solvent is removed. Column chromatographic purification of the residue gives the product in the form of colorless crystals.
Ausbeute: 8,4 g (52 %)Yield: 8.4 g (52%)
IHNMR δ 7,57 (d, 1H) , 7,17 (d, 1H) , 4,64 (t, 1H) , 4,28 (t, 1H), 3,93 (s, 3H) , 3,72 (m, 2H) , 3,30 (t, 1H) , I HNMR δ 7.57 (d, 1H), 7.17 (d, 1H), 4.64 (t, 1H), 4.28 (t, 1H), 3.93 (s, 3H), 3, 72 (m, 2H), 3.30 (t, 1H),
3,10 (m, 1H) .3.10 (m, 1H).
d) Synthese von 9-Chlor-4H- thiochromano [4, 3 -c] isoxazolin- 8- carbonsäured) Synthesis of 9-chloro-4H-thiochromano [4, 3-c] isoxazoline-8-carboxylic acid
Der Methylester aus Stufe c) (7,3 g, 25,7 mmol) in 200 ml Methanol und 200 ml Wasser wurde mit NaOH (1,56 g, 39 mmol) versetzt und 4 h unter Rückfluß erhitzt. Das Methanol wurde entfernt und die wäßrige Phase mit Ether ex- trahiert. Dann säuerte man mit HC1 (konz . ) an, extrahierte mit Ethylacetat, trocknete über Na2S04 und entfernte das Solvens.The methyl ester from step c) (7.3 g, 25.7 mmol) in 200 ml of methanol and 200 ml of water was mixed with NaOH (1.56 g, 39 mmol) and heated under reflux for 4 h. The methanol was removed and the aqueous phase was extracted with ether. Then acidified with HC1 (conc.), Extracted with ethyl acetate, dried over Na 2 S0 4 and the solvent removed.
Ausbeute: 6,75 g (97 %)Yield: 6.75 g (97%)
iHNMR (DMSO) δ 7,62 (d, 1H) , 7,38 (d, 1H) , 9,56 (dd, 1H) , 4,20 (dd, 1H), 3,80 (m, 1H) , 3,32 (m, 2H) . i HNMR (DMSO) δ 7.62 (d, 1H), 7.38 (d, 1H), 9.56 (dd, 1H), 4.20 (dd, 1H), 3.80 (m, 1H) , 3.32 (m, 2H).
e) 9-Chlor-5, 5 -dioxo-4H- thiochromano [4,3-c] isoxazolin- 8- carbonsäuree) 9-chloro-5, 5-dioxo-4H-thiochromano [4,3-c] isoxazoline-8-carboxylic acid
Die Säure aus Stufe d) (4,4 g, 16,3 mmol) wurde in 30 ml Eisessig gelöst und mit einer Spatelspitze Natriumwolframat versetzt. Danach tropfte man bei 50°C Perhydrol (4,16 g, 36,7 mmol) zu und rührte weitere 4 h bei 50°C. Man rührte in Eiswasser ein und extrahierte mit Ethyl- acetat. Die organische Phase wurde mit Wasser gewaschen, über Natriumsulfat getrocknet und eingeengt.The acid from step d) (4.4 g, 16.3 mmol) was dissolved in 30 ml of glacial acetic acid and a spatula tip of sodium tungstate was added. Thereafter, perhydrol (4.16 g, 36.7 mmol) was added dropwise at 50 ° C. and the mixture was stirred at 50 ° C. for a further 4 h. The mixture was stirred into ice water and extracted with ethyl acetate. The organic phase was washed with water, dried over sodium sulfate and concentrated.
Ausbeute: 64 % (3,15 g) Schmp.: 225-227°C.Yield: 64% (3.15 g) mp: 225-227 ° C.
III Herstellung der EndprodukteIII Manufacture of the end products
f) 4- { (9 -Chlor-5, 5 -dioxo-4H- thiochromano [4, 3-c] isoxa- zolin-8-yl) -carbonyl} -5 -hydroxy- 1-methyl -pyrazolf) 4- {(9-Chloro-5, 5-dioxo-4H-thiochromano [4, 3-c] isoxazolin-8-yl) -carbonyl} -5-hydroxy-1-methyl-pyrazole
Die Säure aus Stufe e) (0,8 g, 2,7 mmol) und 5 -Hydroxy- 1-methylpyrazol (0,26 g, 2,7 mmol) in 25 ml Acetonitril wurden mit N,N-Dicyclohexylcarbodiimid (0,55 g, 2,7 mmol) versetzt und bei Raumtemperatur über Nacht gerührt. Man fügte je 50 ml Ethylacetat und 2 % Sodalösung zu, trocknete die organische Phase über Natriumsulfat und entfernte das Solvens. Der Rückstand wurde über Kieselgel gereinigt. Das O-acylierte Produkt wurde in Dioxan mit Kaliumcarbonat (0,17 g, 1,2 mmol) für 6 h am Rückfluß erhitzt. Man fügte je 50 ml Ethylacetat und Wasser zu und wusch die wäßrige Phase mit Ether. Dann stellte man den pH auf 3-4 ein und saugte die sich bildenden Kristalle ab.The acid from stage e) (0.8 g, 2.7 mmol) and 5-hydroxy-1-methylpyrazole (0.26 g, 2.7 mmol) in 25 ml acetonitrile were treated with N, N-dicyclohexylcarbodiimide (0, 55 g, 2.7 mmol) were added and the mixture was stirred at room temperature overnight. 50 ml each of ethyl acetate and 2% sodium carbonate solution were added, the organic phase was dried over sodium sulfate and the solvent was removed. The residue was purified on silica gel. The O-acylated product was refluxed in dioxane with potassium carbonate (0.17 g, 1.2 mmol) for 6 h. 50 ml each of ethyl acetate and water were added and the aqueous phase was washed with ether. Then the pH was adjusted to 3-4 and the crystals formed were suctioned off.
Ausbeute: 0,12 g, 39% Schmp.: 248-249°C.Yield: 0.12 g, 39% mp: 248-249 ° C.
Tabelle 23Table 23
Figure imgf000062_0001
Figure imgf000062_0001
Figure imgf000062_0002
Die Verbindungen I und deren landwirtschaftlich brauchbaren Salze eignen sich - sowohl als Isomerengemische als auch in Form der reinen Isomeren - als Herbizide. Die I enthaltenden herbiziden Mittel bekämpfen Pflanzenwuchs auf Nichtkulturflächen sehr gut, besonders bei hohen Aufwandmengen. In Kulturen wie Weizen, Reis, Mais, Soja und Baumwolle wirken sie gegen Unkräuter und Schadgräser, ohne die Kulturpflanzen nennenswert zu schädigen. Dieser Effekt tritt vor allem bei niedrigen Aufwandmengen auf.
Figure imgf000062_0002
The compounds I and their agriculturally useful salts are suitable - both as isomer mixtures and in the form of the pure isomers - as herbicides. The herbicidal compositions containing I control vegetation very well on non-cultivated areas, particularly when high amounts are applied. In crops such as wheat, rice, corn, soybeans and cotton, they act against weeds and grass weeds without significantly damaging the crop plants. This effect occurs especially at low application rates.
In Abhängigkeit von der jeweiligen Applikationsmethode können die Verbindungen I bzw. sie enthaltende Mittel noch in einer weiteren Zahl von Kulturpflanzen zur Beseitigung unerwünschter Pflanzen eingesetzt werden. In Betracht kommen beispielsweise folgende Kulturen:Depending on the particular application method, the compounds I or compositions containing them can also be used in a further number of crop plants for eliminating undesired plants. 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, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium) , Helianthus annuus, Hevea brasiliensis, Hordeum vulgäre, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec, Manihot esculenta, Medicago sativa, Musa spec, Nicotiana tabacum (N.ru- stica) , Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylestre, Ricinus communis, Saccharum officinarum, Seeale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgäre), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera, Zea mays.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 vulgare, Humulus lupulus, Ipomoealumisisumisum , 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 sylestre, Ricinus communis, Saccharum officinarum, Seeale cereale, Solanum tuberosum, Sorghum bicolor (see vulgar), Theobroma cacao, Trifolium prate nse, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera, Zea mays.
Darüber hinaus können die Verbindungen I auch in Kulturen, die durch Züchtung einschließlich gentechnischer Methoden gegen die Wirkung von Herbiziden tolerant sind, verwandt werden.In addition, the compounds I can also be used in crops which are tolerant to the action of herbicides by breeding, including genetic engineering methods.
Die Applikation der herbiziden Mittel bzw. der Wirkstoffe kann im Vorauflauf- oder im Nachauflaufverfahren erfolgen. Sind die 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) .The herbicidal compositions or the active compounds can be applied pre- or post-emergence. If the active ingredients are less compatible with certain crop plants, application techniques can be used in which the herbicidal compositions are sprayed with the aid of sprayers in such a way that the leaves of the sensitive crop plants are not hit, if possible, while the active ingredients are applied to the leaves underneath growing unwanted plants or the uncovered floor area (post-directed, lay-by).
Die Verbindungen I bzw. die sie enthaltenden herbiziden Mittel können beispielsweise in Form von direkt versprühbaren wäßrigen Lösungen, Pulvern, Suspensionen, auch hochprozentigen wäßrigen, öligen oder sonstigen Suspensionen oder Dispersionen, Emulsionen, 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 I or the herbicidal compositions comprising them can be sprayed or atomized, for example in the form of directly sprayable aqueous solutions, powders, suspensions, including high-strength aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, sprays or granules , Dusting, scattering or pouring. The application forms depend on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
Als inerte Zusatzstoffe kommen im Wesentlichen in Betracht:The following are essentially considered as inert additives:
Mineralölfraktionen von mittlerem bis hohem Siedepunkt, wie Kero- sin oder Dieselöl, ferner Kohlenteeröle sowie Öle pflanzlichen oder tierischen Ursprungs, aliphatische, cyclische und aromatische Kohlenwasserstoffe, z.B. Paraffin, Tetrahydronaphthalin, al- kylierte Naphthaline oder deren Derivate, alkylierte Benzole oder deren Derivate, Alkohole wie Methanol, Ethanol, Propanol, Butanol, Cyclohexanol, Ketone wie Cyclohexanon oder stark polare Lösungsmittel, z. B. Amine wie N-Methylpyrrolidon oder Wasser.Mineral oil fractions from medium to high boiling point, such as kerosene or diesel oil, also coal tar oils as well as oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, alkylated benzenes or their derivatives, alcohols such as methanol, ethanol, propanol, butanol, cyclohexanol, ketones such as cyclohexanone or strongly polar solvents, e.g. B. amines such as N-methylpyrrolidone or water.
Wäßrige Anwendungsformen können aus Emulsionskonzentraten, Suspensionen, Pasten, netzbaren Pulvern oder wasserdispergierbaren Granulaten durch Zusatz von Wasser bereitet werden. Zur Herstellung von Emulsionen, Pasten oder Öldispersionen können die tricyclischen Pyrazolonderivate als solche oder in einem Öl oder Lösungsmittel gelöst, mittels Netz-, Haft-, Dispergier- oder Emulgiermittel in Wasser homogenisiert werden. Es können aber auch aus wirksamer Substanz, Netz-, Haft-, Dispergier- oder Emulgiermittel und eventuell Lösungsmittel oder Öl bestehende Konzentrate hergestellt werden, die zur Verdünnung mit Wasser geeignet sind.Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water. To prepare emulsions, pastes or oil dispersions, the tricyclic pyrazolone derivatives, as such or dissolved in an oil or solvent, can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers. However, it is also possible to prepare concentrates consisting of an active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil, which are suitable for dilution with water.
Als oberflächenaktive Stoffe kommen die Alkali-, Erdalkali-, Ammoniumsalze von aromatischen Sulfonsäuren, z.B. Lignin-, Phenol-, Naphthalin- und Dibutylnaphthalinsulfonsäure, sowie von Fettsäuren, Alkyl- und Alkylarylsulfonaten, Alkyl-, Laurylether- und Fettalkoholsulfaten, sowie Salze sulfatierter Hexa-, Hepta- und Octadecanolen sowie von Fettalkoholglykolether, Kondensationsprodukte von sulfoniertem Naphthalin und seiner Derivate mit Formaldehyd, Kondensationsprodukte des Naphthalins bzw. der Naphthalinsulfonsäuren mit Phenol und Formaldehyd, Polyoxy- ethylenoctylphenolether, ethoxyliertes Isooctyl-, Octyl- oder Nonylphenol, Alkylphenyl-, Tributylphenylpolyglykolether, Alkyl- arylpolyetheralkohole, Isotridecylalkohol, Fettalkoholethylen- oxid-Kondensate, ethoxyliertes Rizinusöl, Polyoxyethylenalkyl- ether oder Polyoxypropylenalkylether, Laurylalkoholpolyglykol- etheracetat, Sorbitester, Lignin-Sulfitablaugen oder Methyl - cellulose in Betracht.The surface-active substances are the alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic acids, for example lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa- , Hepta- and octadecanols 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 or nonylphenyl glycolphenyl, alkylphen - aryl polyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ether or polyoxypropylene alkyl ether, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignin sulfite waste liquors 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, Düngemittel, wie Ammoniumsulfat, Ammoniumphosphat, Ammoniumnitrat, Harnstoffe und pflanzliche Produkte wie Getreidemehl, Baumrinden-, Holz- und Nußschalenmehl, Cellulosepulver oder andere feste Trägerstoffe.Granules, e.g. Coated, impregnated and homogeneous granules can be produced by binding the active ingredients to solid carriers. Solid carriers are mineral soils such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, Urea and vegetable products such as flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.
Die Konzentrationen der Wirkstoffe I in den anwendungsfertigen Zubereitungen können in weiten Bereichen variiert werden. Die Formulierungen enthalten im allgemeinen 0,001 bis 98 Gew.-%, vorzugsweise 0,01 bis 95 Gew.-%, mindestens eines Wirkstoffs. Die Wirkstoffe werden dabei in einer Reinheit von 90% bis 100%, vorzugsweise 95% bis 100% (nach NMR-Sektrum) eingesetzt.The concentrations of the active ingredients I in the ready-to-use preparations can be varied over a wide range. The formulations generally contain 0.001 to 98% by weight, preferably 0.01 to 95% by weight, of at least one active ingredient. The active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).
Die erfindungsgemäßen Verbindungen I können beispielsweise wie folgt formuliert werden:The compounds I according to the invention can be formulated, for example, as follows:
I 20 Gewichtsteile der Verbindung Nr. 23.2 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,I 20 parts by weight of compound no. 23.2 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 Gewichtsteilen Calciumsalz der Dodecylbenzolsulfonsäure und 5 Gewichtsteilen des Anlagerungsproduktes von 40 Mol Ethylenoxid an 1 Mol Ricinusöl besteht. Durch Ausgießen und feines Verteilen der Lösung in 100 000 Gewichtsteilen Wasser erhält man eine wäßrige Dispersion, die 0,02 Gew. % des Wirkstoffs enthält.5 parts by weight of calcium salt of dodecylbenzenesulfonic acid and 5 parts by weight of the adduct 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. 23.2 werden in einer Mischung gelöst, die aus 40 Gewichtsteilen Cyclohexanon, 30 Gewichtsteilen Isobutanol, 20 Gewichtsteilen des Anlage- rungsproduktes von 7 Mol Ethylenoxid an 1 Mol Isooctylphenol und 10 Gewichtsteilen des Anlagerungsproduktes von 40 Mol Ethylenoxid an 1 Mol Ricinusöl besteht. Durch Eingießen und feines Verteilen der Lösung in 100 000 Gewichtsteilen Wasser erhält man eine wäßrige Dispersion, die 0,02 Gew. % des Wirkstoffs enthält.II 20 parts by weight of compound no. 23.2 are dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 mol of ethylene oxide and 1 mol of isooctylphenol and 10 parts by weight of the adduct of 40 mol There is ethylene oxide in 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active ingredient.
III 20 Gewichtsteile des Wirkstoffs Nr. 23.2 werden in einer Mischung gelöst, die aus 25 Gewichtsteilen Cyclohexanon, 65 Gewichtsteilen einer Mineralölfraktion vom Siedepunkt 210 bis 280°C und 10 Gewichtsteilen des Anlagerungsproduktes von 40 Mol Ethylenoxid an 1 Mol Ricinusöl besteht. Durch Eingießen und feines Verteilen der Lösung in 100 000 Gewichtsteilen Wasser erhält man eine wäßrige Dispersion, die 0,02 Gew. % des Wirkstoffs enthält.III 20 parts by weight of active ingredient No. 23.2 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 des Wirkstoffs Nr. 23.2 werden mitIV 20 parts by weight of active ingredient No. 23.2 are with
3 Gewichtsteilen des Natriumsalzes der Diisobutylnaphthalin- sulfonsäure, 17 Gewichtsteilen des Natriumsalzes einer Ligninsulfonsäure aus einer Sulfit-Ablauge und 60 Gewichtsteilen pulverförmigen Kieselsäuregel gut vermischt und in einer Hammermühle vermählen. Durch feines Verteilen der3 parts by weight of the sodium salt of diisobutylnaphthalenesulphonic acid, 17 parts by weight of the sodium salt of lignosulphonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel are mixed well and ground in a hammer mill. By finely distributing the
Mischung in 20 000 Gewichtsteilen Wasser enthält man eine Spritzbrühe, die 0,1 Gew. % des Wirkstoffs enthält.Mixture in 20,000 parts by weight of water contains a spray mixture which contains 0.1% by weight of the active ingredient.
V 3 Gewichtsteile des Wirkstoffs Nr. 23.2 werden mit 97 Gewichtsteilen feinteiligem Kaolin vermischt. Man erhält auf diese Weise ein Stäubemittel, das 3 Gew. % des Wirkstoffs enthält.V 3 parts by weight of active ingredient No. 23.2 are mixed with 97 parts by weight of finely divided kaolin. In this way a dust is obtained which contains 3% by weight of the active ingredient.
VI 20 Gewichtsteile des Wirkstoffs Nr. 23.2 werden mit 2 Gewichtsteilen Calciumsalz der Dodecylbenzolsulfonsäure, 8 Gewichtsteilen Fettalkohol-polyglykolether, 2 Gewichtsteilen Natriumsalz eines Phenol-Harnstoff-Formaldehyd-Kondensates und 68 Gewichtsteilen eines paraffinischen Mineralöls innig vermischt. Man erhält eine stabile ölige Dispersion.VI 20 parts by weight of active ingredient No. 23.2 are intimately mixed with 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 23.2 wird in einer Mischung gelöst, die aus 70 Gewichtsteilen Cyclohexanon, 20 Gewichtsteilen ethoxyliertem Isooctylphenol und 10 Gewichtsteilen ethoxyliertem Rizinusöl besteht. Man erhält ein stabiles Emulsionskonzentrat.VII 1 part by weight of compound 23.2 is dissolved in a mixture consisting of 70 parts by weight of cyclohexanone, 20 parts by weight of ethoxylated isooctylphenol and 10 parts by weight of ethoxylated castor oil. A stable emulsion concentrate is obtained.
VIII 1 Gewichtsteil der Verbindung 23.2 wird in einer Mischung gelöst, die aus 80 Gewichtsteilen Cyclohexanon und 20 Gewichtsteilen Wettol ® EM 31 (nicht ionischer Emulgator auf der Basis von ethoxyliertem Ricinusöl) . Man erhält ein stabiles Emulsionskonzentrat. Zur Verbreiterung des Wirkungsspektrums und zur Erzielung synergistischer Effekte können die tricyclischen Pyrazolonderivate mit zahlreichen Vertretern anderer herbizider oder Wachstums- regulierender Wirkstoffgruppen gemischt und gemeinsam ausgebracht werden. Beispielsweise kommen als MischungspartnerVIII 1 part by weight of compound 23.2 is dissolved in a mixture consisting of 80 parts by weight of cyclohexanone and 20 parts by weight of Wettol® EM 31 (non-ionic emulsifier based on ethoxylated castor oil). A stable emulsion concentrate is obtained. In order to broaden the spectrum of activity and to achieve synergistic effects, the tricyclic pyrazolone derivatives can be mixed with numerous representatives of other herbicidal or growth-regulating active ingredient groups and applied together. For example, come as a mixing partner
1, 2, 4-Thiadiazole, 1, 3 , 4-Thiadiazole, Amide, Aminophosphorsäure und deren Derivate, Aminotriazole, Anilide, (Het) -Aryloxyalkan- säure und deren Derivate, Benzoesäure und deren Derivate, Benzo- thiadiazinone, 2-Aroyl-l, 3-cyclohexandione, Hetaryl-Aryl-Ketone, Benzylisoxazolidmone, Meta-CF3-phenylderivate, Carbamate, Chino- lincarbonsäure und deren Derivate, Chloracetanilide, Cyclo- hexan-1, 3-dionderivate, Diazine, Dichlorpropionsäure und deren Derivate, Dihydrobenzofurane, Dihydrofuran-3-one, Dinitroaniline, Dinitrophenole, Diphenylether, Dipyridyle, Halogencarbonsäuren und deren Derivate, Harnstoffe, 3-Phenyluracile, Imidazole, Imidazolinone, N-Phenyl-3, 4, 5, 6-tetrahydrophthalimide, Oxadiazole, Oxirane, Phenole, Aryloxy- oder Heteroaryloxyphenoxy- propionsäureester, Phenylessigsäure und deren Derivate, Phenyl - propionsäure und deren Derivate, Pyrazole, Phenylpyrazole, Pyridazine, Pyridincarbonsäure und deren Derivate, Pyrimidyl- ether, Sulfonamide, Sulfonylharnstoffe, Triazine, Triazinone, Triazolinone, Triazolcarboxamide, Uracile in Betracht.1, 2, 4-thiadiazoles, 1, 3, 4-thiadiazoles, amides, aminophosphoric acid and their derivatives, aminotriazoles, anilides, (het) -aryloxyalkanoic acid and their derivatives, benzoic acid and their derivatives, benzothiadiazinones, 2-aroyl -l, 3-cyclohexanediones, hetaryl aryl ketones, benzylisoxazolidmones, meta-CF3-phenyl derivatives, carbamates, quinoline carboxylic acids and their derivatives, chloroacetanilides, cyclohexane-1, 3-dione derivatives, diazines, dichloropropionic acid and their derivatives, dihydrobenzene , Dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3, 4, 5, 6-tetrahydrophthalimides, oxadiazoles, oxiranes, pheniranes Aryloxy or heteroaryloxyphenoxy propionic acid esters, phenylacetic acid and its derivatives, phenyl propionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and their derivatives, pyrimidyl ether, sulfonamides, sulfonylurea e, triazines, triazinones, triazolinones, triazolecarboxamides, uraciles.
Außerdem kann es von Nutzen sein, die Verbindungen I allein oder in Kombination mit anderen herbiziden auch noch mit weiteren Pflanzenschutzmitteln gemischt, gemeinsam auszubringen, beispielsweise mit Mitteln zur Bekämpfung von Schädlingen oder phytopathogenen Pilzen bzw. Bakterien. Von Interesse ist ferner die Mischbarkeit mit Mineralsalzlösungen, welche zur Behebung von Ernahrungs- und Spurenelementmängeln eingesetzt werden. Es können auch nichtphytotoxische Öle und Ölkonzentrate zugesetzt werden.It may also be useful to apply the compounds I alone or in combination with other herbicides, mixed with other crop protection agents, for example with agents for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions, which are used to remedy nutritional and trace element deficiencies. Non-phytotoxic oils and oil concentrates can also be added.
Die Aufwandmengen an Wirkstoff betragen je nach Bekämpfungsziel, Jahreszeit, Zielpflanzen und WachstumsStadium 0.001 bis 3.0, vorzugsweise 0.01 bis 1.0 kg/ha aktive Substanz (a. S.)Depending on the target, the season, the target plants and the stage of growth, the active compound application rates are 0.001 to 3.0, preferably 0.01 to 1.0 kg / ha of active substance (see p.)
AnwendungsbeispieleExamples of use
Die herbizide Wirkung der tricyclischen Pyrazolonderivate der Formel I ließ sich durch Gewächshausversuche zeigen:The herbicidal activity of the tricyclic pyrazolone derivatives of the formula I was demonstrated by greenhouse experiments:
Als Kulturgefäße dienten Plastiktöpfe mit lehmigem Sand mit etwa 3,0% Humus als Substrat. Die Samen der Testpflanzen wurden nach Arten getrennt eingesät. Bei Vorauflaufbehandlung wurden die in Wasser suspendierten oder emulgierten Wirkstoffe direkt nach Einsaat mittels fein verteilender Düsen aufgebracht. Die Gefäße wurden leicht beregnet, um Keimung und Wachstum zu fördern, und anschließend mit durchsich- tigen Plastikhauben abgedeckt, bis die Pflanzen angewachsen waren. Diese Abdeckung bewirkt ein gleichmäßiges Keimen der Test- pflanzen, sofern dies nicht durch die Wirkstoffe beeinträchtigt wurde.Plastic pots with loamy sand with about 3.0% humus as substrate served as culture vessels. The seeds of the test plants were sown separately according to species. In pre-emergence treatment, the active ingredients suspended or emulsified in water were applied directly after sowing using finely distributing nozzles. The containers were lightly sprinkled to promote germination and growth, and then covered with clear plastic covers until the plants had grown. This cover causes the test plants to germinate evenly, unless this was affected by the active ingredients.
Zum Zweck der Nachauflaufbehandlung wurden die Testpflanzen je nach Wuchsform erst bis zu einer Wuchshöhe von 3 bis 15 cm angezogen und dann mit den in Wasser suspendierten oder emulgierten Wirkstoffen behandelt. Die Testpflanzen wurden dafür entweder direkt gesät und in den gleichen Gefäßen aufgezogen oder sie wur- den erst als Keimpflanzen getrennt angezogen und einige Tage vor der Behandlung in die Versuchsgefäße verpflanzt. Die Aufwandmenge für die Nachauflaufbehandlung betrug 0.5 bzw. 0. 25 kg/ha a. S.For the purpose of post-emergence treatment, the test plants were first grown to a height of 3 to 15 cm, depending on the growth habit, and then treated with the active ingredients suspended or emulsified in water. For this purpose, the test plants were either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days before the treatment. The application rate for post-emergence treatment was 0.5 or 0.25 kg / ha a. S.
Die Pflanzen wurden artenspezifisch bei Temperaturen von 10 - 25°C bzw. 20 - 35°C gehalten. Die Versuchsperiode erstreckte sich über 2 bis 4 Wochen. Während dieser Zeit wurden die Pflanzen gepflegt, und ihre Reaktion auf die einzelnen Behandlungen wurde ausgewertet.The plants were kept at temperatures of 10 - 25 ° C or 20 - 35 ° C depending on the species. The trial period lasted 2 to 4 weeks. During this time, the plants were cared for and their response to each treatment was evaluated.
Bewertet wurde nach einer Skala von 0 bis 100. Dabei bedeutet 100 kein Aufgang der Pflanzen bzw. völlige Zerstörung zumindest der oberirdischen Teile und 0 keine Schädigung oder normaler Wachstumsverlauf .Evaluation was carried out on a scale from 0 to 100. 100 means no emergence of the plants or complete destruction of at least the aerial parts and 0 means no damage or normal growth.
Die in den Gewächshausversuchen verwendeten Pflanzen setzten sich aus folgenden Arten zusammen:The plants used in the greenhouse experiments are composed of the following types:
Bavercode Deutscher Name Englischer Name CHEAL Weißer Gänsefuß lambsquarters (goosefoot)Bavercode German name English name CHEAL white goose foot lambsquarters (goosefoot)
AMARE Zurückgekrümmter redroot pigweed FuchsschwanzAMARE Curved redroot pigweed foxtail
POLPE Flohknöterich ladysthumbPOLPE knotweed ladysthumb
SOLNI Schwarzer Nachtblack nightshade schattenSOLNI Black night black nightshade shade
VERSS Ehrenpreisarten speedwellVERSS speedwell honorary prize types
Bei Aufwandmengen von 0,25 bzw. 0,5 kg/ha a.S. zeigte die Verbindung 23.2 im Nachauflaufverfahren eine sehr gute Wirkung gegen die unerwünschten Pflanzen weißer Gänsefuß, zurückgekrümmter Fuchsschwanz, Flohknöterich, schwarzer Nachtschatten und Ehrenpreisarten. At application rates of 0.25 or 0.5 kg / ha aS, the compound 23.2 showed a very good effect against the undesirable plants of white goose foot, more curved backwards Foxtail, flea knotweed, black nightshade and honorary prize types.

Claims

Patentansprücheclaims
1. Tricyclische Pyrazolonderivate der Formel I1. Tricyclic pyrazolone derivatives of the formula I.
Figure imgf000070_0001
Figure imgf000070_0001
in der die Substituenten folgende Bedeutung haben:in which the substituents have the following meaning:
R Wasserstoff, Cι-C6-Alkyl, Cι-C6-Haloalkyl,R is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl,
Cι-C6-Alkoxy, Ci-Ce-Haloalkoxy, Ci-Cδ-Alkylthio, Cι-C6-Haloalkylthio, Cι-C6-Alkylsulfinyl, Ci-Cβ-Haloalkylsulfinyl, Ci-Cβ-Alkylsulfonyl,Cι-C 6 alkoxy, Ci-Ce-haloalkoxy, Ci-C δ alkylthio, Cι-C 6 haloalkylthio, Cι-C 6 alkylsulfinyl, Ci-Cβ-haloalkylsulfinyl, Ci-Cβ alkylsulfonyl,
Cι-C6-Haloalkylsulfonyl, Halogen, Cyano- oder Nitro;-CC 6 haloalkylsulfonyl, halogen, cyano- or nitro;
X 0 oder NR2;X 0 or NR 2 ;
R2 Wasserstoff, Ci-Cδ-Alkyl, Cι-C6-Alkoxy,R 2 is hydrogen, Ci-C δ -alkyl, C 6 alkoxy,
Ci-Cδ-Haloalkyl, Ci-Cδ-Haloalkoxy, gegebenenfalls mit Cι-C3 -Alkyl, Halogen, Cyano, Nitro oder Cι-C3-Alkylsulfonyl substituiertes Phenyl oder gegebenenfalls mit Cι-C3 -Alkyl, Halogen, Cyano oder Nitro substituiertes Phenylsulfonyl;Ci-C δ- haloalkyl, Ci-C δ -haloalkoxy, optionally substituted with C 1 -C 3 alkyl, halogen, cyano, nitro or C 1 -C 3 alkylsulfonyl or optionally substituted with C 1 -C 3 alkyl, halogen, cyano or nitro substituted phenylsulfonyl;
R3, R4 Wasserstoff, Cι-C6-Alkyl, Cι-C6-Haloalkyl,R 3 , R 4 are hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl,
Cι-C6-Alkoxy, Ci-Cδ-Haloalkoxy, Cι-C6-Alkylthio, Cι-C6-Haloalkylthio, Cι-C6-Alkylsulfinyl,Cι-C 6 -alkoxy, C δ haloalkoxy, Cι-C 6 alkylthio, Cι-C 6 haloalkylthio, Cι-C 6 alkylsulfinyl,
Ci-Cβ-Haloalkylsulfinyl, Cι-C6-Alkylsulfonyl, Cχ-C6-Haloalkylsulfonyl, NR7R8, C2-C6-Alkoxy- alkyl, Cι-C6 -Alkoxycarbonyl, Ci-Cß-Alkylcarbonyl, Halogen, Cyano, Nitro, gegebenenfalls mit Cχ-C3 -Alkyl, Halogen, Cyano oder Nitro substituiertes Phenyl;Ci-Cβ-haloalkylsulfinyl, Cι-C 6 alkylsulfonyl, Cχ-C 6 -haloalkylsulfonyl, NR 7 R 8 , C 2 -C 6 alkoxyalkyl, Cι-C 6 alkoxycarbonyl, Ci-C ß -alkylcarbonyl, halogen , Cyano, nitro, optionally substituted with Cχ-C 3 alkyl, halogen, cyano or nitro;
R5 Wasserstoff oder Ci-C4-Alkyl;R 5 is hydrogen or Ci-C 4 alkyl;
R6 Wasserstoff, Cι-C6-Alkyl oder Halogen; R7 Wasserstof f oder Ci - Cβ -Alkyl ;R 6 is hydrogen, -CC 6 alkyl or halogen; R 7 is hydrogen or Ci - Cβ alkyl;
R8 Ci -Ce -Alkyl oder Cι -C6 -AlkoxyR 8 Ci -Ce alkyl or -C -C 6 alkoxy
1 0 , 1 oder 2 ;1 0, 1 or 2;
n 1 oder 2 ;n 1 or 2;
R9 ein Rest Ha oder Ilb ,R9 is a remainder Ha or Ilb,
Figure imgf000071_0001
lla Ilb wobei die Variablen folgende Bedeutung haben:
Figure imgf000071_0001
lla Ilb where the variables have the following meaning:
Rio Hydroxy, Mercapto, Halogen, ORi3, SRi3, SORi4,Rio Hydroxy, Mercapto, Halogen, OR i3 , SR i3 , SORi 4 ,
S02R14, OS02Rl4, P(0)Rl5Rl6, OP(0)Rl5Rl6, P(S)Rl5Rl6, OP(S)Ri5Ri6, NRi7R8, ONRi4Ri4 oder N-gebundenes Heterocyclyl, das partiell oder vollständig halo- geniert sein kann und/oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, C1-C4 -Alkyl, C1-C4 -Halogenalkyl, C1-C4 -Alkoxy oder Cι-C4-Ha- logenalkoxy;S0 2 R 14, OS0 2 R l4, P (0) R l5 R l6, OP (0) R l5 R l6, P (S) R l5 R l6, OP (S) R i5 R i6, NR i7 R 8 , ONR i4 R i4 or N-linked heterocyclyl, which can be partially or completely halogenated and / or can carry one to three of the following radicals: nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 - haloalkyl, C 1 -C 4 alkoxy or Cι-C logenalkoxy 4 -Ha-;
RU Wasserstoff, Ci-Cδ-Alkyl, Cι-C6-Halogenalkyl,RU is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl,
Ci-Cδ-Alkoxy oder Ci-Cβ-Halogenalkoxy;Ci-C δ alkoxy or Ci-Cβ-haloalkoxy;
Ri2 Wasserstoff, Halogen, Ci-Cδ-Alkyl, Ci-Cβ-Halogenal- kyl, Ci-Cδ-Alkoxy, Ci-Cδ-Halogenalkoxy, Cι-C6-Al- kylthio oder Ci-Cδ-Halogenalkylthio;Ri 2 is hydrogen, halogen, Ci-C δ- alkyl, Ci-Cβ-halo-alkyl, Ci-C δ- alkoxy, Ci-Cδ-haloalkoxy, Cι-C 6 -alkyl thio or Ci-C δ -haloalkylthio;
R3 Ci-Cδ-Alkyl, C3-C6-Alkenyl, C3-C6-Halogenalkenyl, C3-Cδ-Alkinyl, C3-Cδ-Halogenalkinyl, C3-Cδ-Cyclo- alkyl, Ci-Cδ-Alkylcarbonyl, C2-Cδ-Alkenylcarbonyl, C2-Cδ-Alkinylcarbonyl, C3-Cδ-Cycloalkylcarbonyl,R 3 Ci-C δ alkyl, C 3 -C 6 alkenyl, C 3 -C 6 haloalkenyl, C 3 -C δ alkynyl, C 3 -C δ haloalkynyl, C 3 -C δ cycloalkyl , Ci-C δ -alkylcarbonyl, C 2 -C δ- alkenylcarbonyl, C 2 -C δ -alkynylcarbonyl, C 3 -C δ -cycloalkylcarbonyl,
Ci-Cδ-Alkoxycarbonyl , C3-Cβ-Alkenyloxycarbonyl, C3-Cδ-Alkinyloxycarbonyl, Ci-Cδ -Alkylthiocarbonyl, Ci-Cβ-Alkylaminocarbonyl, C3-C6-Alkenylaminocarbo- nyl, C3-Cδ-Alkinylaminocarbonyl, N,N-Di- (Ci-Cδ- alkyl) -aminocarbonyl, N- (C3-Cδ-Alkenyl) -N- (Ci-Cδ- alkyl) -aminocarbonyl, N- (C3-Cδ-Alkinyl) -N- (Ci-Cβ- alkyl) -aminocarbonyl, N- (Ci-Cδ-Alkoxy) -N- (Ci-Cδ- alkyl) -aminocarbonyl, N- (C3-Cδ-Alkenyl) -N- (QL-CÖ- alkoxy) -aminocarbonyl , N- (C3-Cδ-Alkinyl ) -N- (Ci-Cδ- alkoxy) -aminocarbonyl , Di- (Ci-Cδ-alkyl) -aminothiocarbonyl oder Ci-Cδ-Alkoxyimino-Ci-Cδ-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, C1-C4-Alkylthio, Di- (Cι-C4-alkyl) -amino, Cι-C4-Alkylcarbonyl, Cι-C4-Alkoxycarbonyl, Cι-C4-Alkoxy-Cι-C4-alkoxy- carbonyl, Hydroxycarbonyl, Cι-C4-Alkylaminocarbo- nyl, Di- (Cι-C4-alkyl) -aminocarbonyl, Aminocarbonyl, Cι-C4-Alkylcarbonyloxy oder C3-Cδ-Cycloalkyl;Ci-C δ alkoxycarbonyl, C 3 -Cβ-alkenyloxycarbonyl, C 3 -C δ- alkynyloxycarbonyl, Ci-C δ- alkylthiocarbonyl, Ci-Cβ-alkylaminocarbonyl, C 3 -C 6 -alkenylaminocarbonyl, C 3 -C δ -Alkynylaminocarbonyl, N, N-di- (Ci-C δ -alkyl) -aminocarbonyl, N- (C 3 -Cδ-alkenyl) -N- (Ci-C δ -alkyl) -aminocarbonyl, N- (C 3 - C δ- alkynyl) -N- (Ci-Cβ-alkyl) -aminocarbonyl, N- (Ci-C δ- alkoxy) -N- (Ci-C δ - alkyl) -aminocarbonyl, N- (C 3 -C δ- alkenyl) -N- (Q L -C Ö - alkoxy) -aminocarbonyl, N- (C 3 -C δ- alkynyl) -N- (Ci-C δ - alkoxy) -aminocarbonyl, di- (Ci-C δ- alkyl) -aminothiocarbonyl or Ci-C δ -alkoxyimino-Ci-C δ -alkyl, where the alkyl, cycloalkyl and alkoxy radicals mentioned can be partially or completely halogenated and / or may carry one to three of the following groups: cyano, C 4 alkoxy, C 1 -C 4 alkylthio, di (Cι-C4 alkyl) amino, Cι-C 4 alkylcarbonyl, Cι- C 4 -alkoxycarbonyl, -C-C 4 -alkoxy-Cι-C 4 -alkoxy- carbonyl, hydroxycarbonyl, Cι-C 4 -alkylaminocarbonyl, di- (-C-C 4 alkyl) aminocarbonyl, aminocarbonyl, Cι-C 4- alkylcarbonyloxy or C 3 -C δ cycloalkyl;
Phenyl, Phenyl-Ci-Cδ-alkyl, Phenylcarbo- nyl-Ci-Cδ-alkyl, Phenylcarbonyl, Phenoxycarbonyl, Phenyloxythiocarbonyl , Phenylaminocarbonyl, N- (Cι-C6-Alkyl) -N- (phenyl) -aminocarbonyl, Phe- nyl-C2-Cδ-alkenylcarbonyl, Heterocyclyl, Heterocy- clyl-Ci-Cδ-alkyl, Heterocyclylcarbonyl -Ci-Cδ-alkyl,Phenyl, phenyl-Ci-C δ- alkyl, phenylcarbonyl-Ci-C δ- alkyl, phenylcarbonyl, phenoxycarbonyl, phenyloxythiocarbonyl, phenylaminocarbonyl, N- (-C 6 alkyl) -N- (phenyl) aminocarbonyl, Phe - nyl-C 2 -Cδ-alkenylcarbonyl, heterocyclyl, heterocyclyl-C δ -alkyl, heterocyclylcarbonyl-C -C alkyl δ,
Heterocyclylcarbonyl, Heterocyclyloxycarbonyl, Heterocyclyloxythiocarbonyl , Heterocyclylaminocarbo- nyl, N- (Ci-Cδ-Alkyl) -N- (heterocyclyl) -aminocarbonyl, oder Heterocyclyl-C2-Cδ-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, C1-C4-Alkyl, C1-C4-Halogenalkyl, C1-C4-Alkoxy oder Cι-C-Halogenalkoxy;Heterocyclylcarbonyl, heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl, heterocyclylaminocarbonyl, N- (Ci-Cδ-alkyl) -N- (heterocyclyl) -aminocarbonyl, or heterocyclyl-C 2 -C δ -alkenylcarbonyl, with the phenyl- and the residue being the phenyl- and the phenyl- the latter substituent can be partially or completely halogenated and / or can carry one to three of the following radicals: nitro, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or Cι- C-haloalkoxy;
Ci-Cδ-Alkyl, C3-C6-Alkenyl, C3-C6-Alkinyl oderCi-C δ alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl or
C3-C6-Cycloalkyl, wobei die vier genannten Reste partiell oder vollständig halogeniert sein können und/oder eine bis drei der folgenden Gruppen tragen können: Cyano, Cι~C4-Alkoxy, C1-C4 -Halogenalkoxy, Cι-C4-Alkylthio, Cι-C -Halogenalkylthio, Cι-C4-Alkylcarbonyl, C1-C4-Alkoxycarbonyl oder Cι-C4-Halogenalkoxycarbonyl;C 3 -C 6 -cycloalkyl, where the radicals mentioned four may be partially or fully halogenated and / or may carry one to three of the following groups: cyano, ~ C 4 alkoxy, C 1 -C 4 haloalkoxy, Cι- C 4 -alkylthio, -C-C -haloalkylthio, -C-C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl or Cι-C 4 -haloalkoxycarbonyl;
Phenyl, Phenyl-Ci-Cβ-alkyl, Heterocyclyl oder Hete- rocyclyl-Ci-Cβ-alkyl, wobei der Phenyl- und der He- terocyclyl-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-Halogen- alkyl, C1-C4-Alkoxy, Cι-C4-Halogenalkoxy oder C1-C4- Alkoxycarbonyl;Phenyl, phenyl-Ci-Cβ-alkyl, heterocyclyl or heterocyclyl-Ci-Cβ-alkyl, where the phenyl and heterocyclyl radicals of the latter substituents can be partially or completely halogenated and / or one to three of the following can carry radicals: nitro, cyano, C 4 -alkyl, halo-C 4 alkyl, C 1 -C 4 -alkoxy, C 4 -haloalkoxy or C 1 -C 4 - alkoxycarbonyl;
Rs, Riß Wasserstoff, Hydroxy, Cι-C6 -Alkyl, Cι-C6 -Alkoxy, Cι-C6-Alkylthio, Phenyl, Phenyl-C1-C4-alkyl oderRs, crack hydrogen, hydroxy, -C 6 alkyl, -C 6 alkoxy, -C 6 alkylthio, phenyl, phenyl-C 1 -C 4 -alkyl or
Phenoxy, wobei die drei letztgenannten Substituenten partiell oder vollständig halogeniert sein können und/oder einen bis drei der folgenden Reste tragen können: Nitro, Cyano, Cι-C4-Alkyl, C1-C4 -Halogenalkyl, Cι-C4-Alkoxy,Phenoxy, where the three last-mentioned substituents 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, Cι-C 4 alkoxy ,
C1-C4 -Halogenalkoxy oder C1-C4 -Alkoxycarbonyl;C 1 -C 4 haloalkoxy or C 1 -C 4 alkoxycarbonyl;
Ri Wasserstoff, Cι-C6-Alkyl, C3-C6 -Alkenyl,Ri hydrogen, -CC 6 alkyl, C 3 -C 6 alkenyl,
C3-Cδ-Halogenalkenyl, C3-C6 -Alkinyl, C3 -C6-Halogen- alkinyl, C3-Cδ -Cycloalkyl, Cι-C6-Alkylcarbonyl,C 3 -C δ haloalkenyl, C 3 -C 6 alkynyl, C 3 -C 6 haloalkynyl, C 3 -C δ cycloalkyl, C 1 -C 6 alkylcarbonyl,
Hydroxy, Ci-Cδ -Alkoxy, C3-Cδ-Alkenyloxy, C3-Cδ-Alkinyloxy, Amino, Ci-Cδ-Alkylamino, Di- (Ci-Cδ-alkyl) -amino oder Ci-Cδ-Alkylcarbonyl- 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, C1-C4-Alkoxycarbonyl, Cι-C -Alkylaminocarbonyl, Di- (C1-C4- alkyl) -aminocarbonyl oder C3 -C6-Cycloalkyl;Hydroxy, Ci-Cδ-alkoxy, C 3 -Cδ-alkenyloxy, C 3 -C δ- alkynyloxy, amino, Ci-C δ -alkylamino, di- (Ci-C δ -alkyl) -amino or Ci-C δ - 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, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkylaminocarbonyl, di - (C 1 -C 4 alkyl) aminocarbonyl or C 3 -C 6 cycloalkyl;
Phenyl, Phenyl -C1-C4-alkyl, Phenylcarbonyl, Heterocyclyl, Heterocyclyl-C1-C4-alkyl oder Heterocyclylcarbonyl, wobei der Phenyl- oder Heterocyclyl-Rest der sechs letztgenannten Substituenten partiell oder vollständig halogeniert sein kann und/oder einen bis drei der folgenden Reste tragen kann: Nitro, Cyano, Cι-C4-Alkyl, C1-C4 -Halogenalkyl, Cι-C -Alkoxy oder Ci-C -Halogenalkoxy;Phenyl, phenyl -C 1 -C4-alkyl, phenylcarbonyl, heterocyclyl, heterocyclyl-C 1 -C 4 -alkyl or heterocyclylcarbonyl, it being possible for the phenyl or heterocyclyl radical of the six latter substituents to be partially or completely halogenated and / or one to can carry three of the following radicals: nitro, cyano, C 4 alkyl, C 1 -C 4 haloalkyl, Cι-C alkoxy or Ci-C -haloalkoxy;
R18 Wasserstoff, Ci-Cδ-Alkyl oder C3-C6 -Alkenyl,R 18 is hydrogen, Ci-Cδ-alkyl or C 3 -C 6 alkenyl,
C3 -Cδ"Alkinyl;C 3 -C δ "alkynyl;
sowie deren landwirtschaftlich brauchbaren Salze.and their agriculturally useful salts.
2. Tricyclische Pyrazolonderivate der Formel III gemäß Anspruch 1
Figure imgf000074_0001
2. tricyclic pyrazolone derivatives of the formula III according to claim 1
Figure imgf000074_0001
in der die Substituenten die in Anspruch 1 angegebenen Bedeutungen haben.in which the substituents have the meanings given in claim 1.
3. Tricyclische Pyrazolonderivate der Formel III nach Anspruch 2, in der der Substituent R9 die in Anspruch 1 angegebene Be- deutung hat und die übrigen Substituenten die folgende Bedeutung haben:3. Tricyclic pyrazolone derivatives of the formula III according to claim 2, in which the substituent R 9 has the meaning given in claim 1 and the other substituents have the following meaning:
Rl Wasserstoff, Cι-C6 -Alkyl, Cι-C6-Haloalkyl, Ci-Cδ-Alkoxy, Cι-C6-Alkylthio, Cι-C6-Alkyl- sulfonyl, Halogen, Cyano- oder Nitro;R l are hydrogen, C 6 -alkyl, C 6 haloalkyl, Ci-C δ -alkoxy, C 6 alkylthio, Cι-C 6 alkyl sulfonyl, halogen, cyano or nitro;
R3, R4 Wasserstoff, Ci-Cβ-Alkyl, Ci-Cδ-Alkoxy, Cι-C6-Alkylthio, Cι-C6-Alkylsulfonyl, C2 -C6 -Alkoxyalkyl, Ci-Cδ -Alkoxycarbonyl, Ci-Cδ-Alkylcarbonyl, Halogen, gegebenenfalls mit Cι-C3 -Alkyl, Halogen, Cyano oder Nitro substituiertes Phenyl;R 3 , R 4 are hydrogen, Ci-Cβ-alkyl, Ci-C δ alkoxy, Cι-C 6 alkylthio, Cι-C 6 alkylsulfonyl, C 2 -C 6 alkoxyalkyl, Ci-C δ alkoxycarbonyl, Ci -C δ alkylcarbonyl, halogen, phenyl optionally substituted with C 1 -C 3 alkyl, halogen, cyano or nitro;
R5 Wasserstoff;R5 is hydrogen;
R6 Wasserstoff, Cι-C3-Alkyl oder Halogen;R 6 is hydrogen, -CC 3 -alkyl or halogen;
n 1 oder 2.n 1 or 2.
4. Tricyclische Pyrazolonderivate der Formel IV gemäß Anspruch 14. tricyclic pyrazolone derivatives of the formula IV according to claim 1
Figure imgf000074_0002
in der die Substituenten die in Anspruch 1 angegebenen Bedeutungen haben.
Figure imgf000074_0002
in which the substituents have the meanings given in claim 1.
5. Tricyclische Pyrazolonderivate der Formel IV nach Anspruch 4, in der der Substituent R9 die in Anspruch 1 angegebene Bedeutung hat und die übrigen Substituenten die folgende Bedeutung haben:5. Tricyclic pyrazolone derivatives of the formula IV according to claim 4, in which the substituent R 9 has the meaning given in claim 1 and the other substituents have the following meaning:
Ri Wasserstoff, Cι-C6 -Alkyl, Cι-C6-Haloalkyl, Ci-Cδ -Alkoxy, Cι-C6-Alkylthio, Cι-C6-Alkylsulfonyl, Halogen, Cyano oder Nitro;Ri are hydrogen, C 6 -alkyl, C 6 haloalkyl, Ci-C δ -alkoxy, C 6 alkylthio, Cι-C 6 alkylsulfonyl, halo, cyano or nitro;
R2 Wasserstoff, Cι-C6-Alkyl, Cι-C6-Alkoxy,R 2 is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy,
Ci-Cδ-Haloalkyl, Ci-Cδ-Haloalkoxy, gegebenenfalls mit Cι-C3 -Alkyl, Halogen, Cyano, Nitro oderCi-C δ- haloalkyl, Ci-Cδ-haloalkoxy, optionally with -C-C 3 alkyl, halogen, cyano, nitro or
Cι-C3-Alkylsulfonyl substituiertes Phenyl oder gegebenenfalls mit Cι-C3 -Alkyl, Halogen, Cyano oder Nitro substituiertes Phenylsulfonyl;C 1 -C 3 alkylsulfonyl substituted phenyl or phenylsulfonyl optionally substituted with C 1 -C 3 alkyl, halogen, cyano or nitro;
R3, R4 Wasserstoff, Cι-C6-Alkyl, Cι-C6 -Alkoxy,R 3 , R 4 are hydrogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy,
Cι-C6- lkylthio, Cι-C6-Alkylsulfonyl, C -Cδ -Alkoxyalkyl, Ci-Cδ-Alkoxycarbonyl, Ci-Cδ-Alkylcarbonyl, Halogen, gegebenenfalls mit Cι-C3 -Alkyl, Halogen, Cyano oder Nitro substi- tuiertes Phenyl;-C-C 6 - lkylthio, -C-C 6 alkylsulfonyl, C -C δ alkoxyalkyl, Ci-C δ alkoxycarbonyl, Ci-C δ alkylcarbonyl, halogen, optionally with Cι-C 3 alkyl, halogen, cyano or Nitro substituted phenyl;
R5 Wasserstoff;R 5 is hydrogen;
R6 Wasserstoff, Cι-C3-Alkyl oder Halogen;R 6 is hydrogen, -CC 3 -alkyl or halogen;
n 1 oder 2.n 1 or 2.
6. Verfahren zur Herstellung von Verbindungen der Formel I mit Rio = Hydroxy, gemäß Anspruch 1, dadurch gekennzeichnet, daß man ein Pyrazolon der Formel XII,6. A process for the preparation of compounds of the formula I with Rio = hydroxy, according to claim 1, characterized in that a pyrazolone of the formula XII,
Figure imgf000075_0001
Figure imgf000075_0001
wobei die Variablen R11 und R12 die in Anspruch 1 genannte Bedeutung haben, mit einer aktivierten Carbonsäure Va oder einer Carbonsäure Vb
Figure imgf000076_0001
where the variables R 11 and R 12 have the meaning given in claim 1, with an activated carboxylic acid Va or a carboxylic acid Vb
Figure imgf000076_0001
Va VbVa vb
wobei die Variablen R1 bis R6, X, 1 und n die unter Anspruch 1 genannte Bedeutung haben und Lx für eine nukleophil verdräng- bare Abgangsgruppe steht, acyliert und das Acylierungsprodukt ggf . in Gegenwart eines Katalysators zu den Verbindungen I mit Ri° = Hydroxy umlagert.where the variables R 1 to R 6 , X, 1 and n have the meaning given under claim 1 and L x stands for a nucleophilically displaceable leaving group, acylated and the acylation product if necessary. rearranged in the presence of a catalyst to give the compounds I with R i ° = hydroxy.
Herbizides Mittel, enthaltend mindestens ein tricyclisches Pyrazolonderivat der Formel I gemäß Anspruch 1 und übliche inerte Zusatzstoffe.Herbicidal agent containing at least one tricyclic pyrazolone derivative of the formula I according to claim 1 and customary inert additives.
8. Verfahren zur Bekämpfung unerwünschten Pflanzenwuchses, dadurch gekennzeichnet, daß man eine herbizid wirksame Menge eines tricyclischen Pyrazolonderivates der Formel I gemäß Anspruch 1 auf die Pflanzen oder deren Lebensraum einwirken läßt. 8. A method for controlling undesirable plant growth, characterized in that a herbicidally effective amount of a tricyclic pyrazolone derivative of the formula I according to claim 1 is allowed to act on the plants or their habitat.
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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0286346A2 (en) * 1987-04-09 1988-10-12 E.I. Du Pont De Nemours And Company Insecticidal substituted indazoles
EP0365201A1 (en) * 1988-10-11 1990-04-25 E.I. Du Pont De Nemours And Company Substituted indazoles as arthropodicides
WO1997019087A1 (en) * 1995-11-17 1997-05-29 E.I. Du Pont De Nemours And Company Tricyclic herbicidal heterocycles
WO1997042185A1 (en) * 1996-05-07 1997-11-13 E.I. Du Pont De Nemours And Company 1,2-benzoxathiin and thiepin 2,2-dioxide herbicides
WO1998028291A1 (en) * 1996-12-20 1998-07-02 E.I. Du Pont De Nemours And Company Substituted benzothiopyranes salts and their use as herbicides
EP0860441A1 (en) * 1997-02-24 1998-08-26 E.I. Du Pont De Nemours And Company Herbicidal derivatives of 1,4-dithiino(2,3c)benzothiopyran

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0286346A2 (en) * 1987-04-09 1988-10-12 E.I. Du Pont De Nemours And Company Insecticidal substituted indazoles
EP0365201A1 (en) * 1988-10-11 1990-04-25 E.I. Du Pont De Nemours And Company Substituted indazoles as arthropodicides
WO1997019087A1 (en) * 1995-11-17 1997-05-29 E.I. Du Pont De Nemours And Company Tricyclic herbicidal heterocycles
WO1997042185A1 (en) * 1996-05-07 1997-11-13 E.I. Du Pont De Nemours And Company 1,2-benzoxathiin and thiepin 2,2-dioxide herbicides
WO1998028291A1 (en) * 1996-12-20 1998-07-02 E.I. Du Pont De Nemours And Company Substituted benzothiopyranes salts and their use as herbicides
EP0860441A1 (en) * 1997-02-24 1998-08-26 E.I. Du Pont De Nemours And Company Herbicidal derivatives of 1,4-dithiino(2,3c)benzothiopyran

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