WO2000059910A2 - Derives tricycliques de pyrazolone - Google Patents

Derives tricycliques de pyrazolone 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)
English (en)
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WO2000059910A3 (fr
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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/fr
Publication of WO2000059910A3 publication Critical patent/WO2000059910A3/fr

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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.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Dérivés tricycliques de pyrazolone de formule (I) dans laquelle R<1> représente hydrogène, alkyle C1-C6, haloalkyle C1-C6, alcoxy C1-C6, haloalcoxy C1-C6, alkylthio C1-C6, haloalkylthio C1-C6, alkylsulfinyle C1-C6, haloalkylsulfinyle C1-C6, alkylsulfonyle C1-C6, haloalkylsulfonyle C1-C6, halogène, cyano- ou nitro; X représente O ou NR<2>; R<2> représente hydrogène, alkyle C1-C6, alcoxy C1-C6, haloalkyle C1-C6, haloalcoxy C1-C6, phényle éventuellement substitué par alkyle C1-C3, halogène, cyano, nitro ou alkylsulfonyle C1-C3 ou phénylsulfonyle éventuellement substitué par alkyle C1-C3, halogène, cyano ou nitro; R<3> et R<4> représentent hydrogène, alkyle C1-C6, haloalkyle C1-C6, alcoxy C1-C6, haloalcoxy C1-C6, alkylthio C1-C6, haloalkylthio C1-C6, alkylsulfinyle C1-C6, haloalkylsulfinyle C1-C6, alkylsulfonyle C1-C6, haloalkylsulfonyle C1-C6, NR<7>R<8>, alcoxyalkyle C2-C6, alcoxycarbonyle C1-C6, alkylcarbonyle C1-C6, halogène, cyano, nitro, phényle éventuellement substitué par alkyle C1-C3, halogène, cyano ou nitro; R<5> représente hydrogène ou alkyle C1-C4; R<6> représente hydrogène, alkyle C1-C6 ou halogène; R<7> représente hydrogène ou alkyle C1-C6; R<8> représente alkyle C1-C6 ou alcoxy C1-C6; l représente 0, 1 ou 2; n représente 1 ou 2; R<9> représente un reste de formule (IIa) ou (IIb) dans lesquelles les variables possèdent la signification figurant à la revendication 1. La présente invention concerne encore un procédé de préparation desdits dérivés tricycliques de pyrazolone, des substances qui les contiennent ainsi que l'utilisation de ces dérivés ou des substances qui les contiennent pour la lutte contre les mauvaises herbes.
PCT/EP2000/002564 1999-04-01 2000-03-23 Derives tricycliques de pyrazolone WO2000059910A2 (fr)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0286346A2 (fr) * 1987-04-09 1988-10-12 E.I. Du Pont De Nemours And Company Indazoles substitués insecticides
EP0365201A1 (fr) * 1988-10-11 1990-04-25 E.I. Du Pont De Nemours And Company Indazoles substitués comme arthropodicides
WO1997019087A1 (fr) * 1995-11-17 1997-05-29 E.I. Du Pont De Nemours And Company Heterocycles herbicides tricycliques
WO1997042185A1 (fr) * 1996-05-07 1997-11-13 E.I. Du Pont De Nemours And Company Herbicides a base de 2,2-dioxydes de 1,2-benzoxathiine et de 1,2-thiepine
WO1998028291A1 (fr) * 1996-12-20 1998-07-02 E.I. Du Pont De Nemours And Company Sels de benzothiopyranes substitues et leur utilisation comme herbicide
EP0860441A1 (fr) * 1997-02-24 1998-08-26 E.I. Du Pont De Nemours And Company Dérivés de 1,4-dithiino(2,3c)benzothiopyran comme herbizides

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0286346A2 (fr) * 1987-04-09 1988-10-12 E.I. Du Pont De Nemours And Company Indazoles substitués insecticides
EP0365201A1 (fr) * 1988-10-11 1990-04-25 E.I. Du Pont De Nemours And Company Indazoles substitués comme arthropodicides
WO1997019087A1 (fr) * 1995-11-17 1997-05-29 E.I. Du Pont De Nemours And Company Heterocycles herbicides tricycliques
WO1997042185A1 (fr) * 1996-05-07 1997-11-13 E.I. Du Pont De Nemours And Company Herbicides a base de 2,2-dioxydes de 1,2-benzoxathiine et de 1,2-thiepine
WO1998028291A1 (fr) * 1996-12-20 1998-07-02 E.I. Du Pont De Nemours And Company Sels de benzothiopyranes substitues et leur utilisation comme herbicide
EP0860441A1 (fr) * 1997-02-24 1998-08-26 E.I. Du Pont De Nemours And Company Dérivés de 1,4-dithiino(2,3c)benzothiopyran comme herbizides

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