Classifications

• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
  • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
  • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
  • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
  • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D231/18—One oxygen or sulfur atom
  • C07D231/20—One oxygen atom attached in position 3 or 5

Definitions

• the present invention relates to cycloalkyl-substituted benzoylpyrazoles of the formula I.
• R2 is hydrogen, C ⁇ -0 6 -alkyl, C ⁇ -C 6 -alkoxy, C ⁇ -C 6 -alkyl thio, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, halogen, nitro, -S (0 ) n R 8 , -S0 2 OR 9 , -S0 2 NR 9 R 10 , -NR 10 SO 2 R 1: L , -NR ⁇ COR 11 , -PO (OR 12 ) (OR 13 ),;
• R 3 is hydrogen, halogen, C; ⁇ .-C 6 alkyl, Ci-C ⁇ -halo- alkyl, Ci-COE-alkoxy, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl;
• R 4 , R 5 hydrogen, nitro, halogen, cyano, rhodano,
• C ⁇ -C6 alkyl, Ci-C ⁇ -haloalkyl, C 3 -C 6 cycloalkyl, C 2 -C 6 alkenyl, C 4 -C 6 cycloalkenyl, C 2 -C 6 alkynyl, C ⁇ -C 6 - Alkylthio, -C-C 6 -haloalkoxy, -COR 12 , -C0 2 R 12 , -COSR 12 , -CONR 12 R 13 , -C (R 14 ) NR 15 ,
• -P0 (0R 12 ) (OR 13 ), -C -C alkyl, which carries a radical from the following group: -COR 12 , -CO 2 R 12 , -COSR 12 , -C0NR 12 R 13 or -C (R 14 ) NR 15 ; Heterocyclyl, heterocyclic -CC 4 -alkyl, phenyl, phenyl -CC 4 -alkyl, hetaryl or hetaryl -CC 4 -alkyl, where the latter six radicals may be substituted; or
• R 4 and R 5 form a screened lonely C 2 -C 6 -alkanediyl chain which is mono- to tetrasubstituted by C ⁇ -C4 ⁇ alkyl may be substituted and / or by oxygen or sulfur or an optionally C ⁇ -C 4 alkyl substituted nitrogen interrupted can be;
• R 6 is hydrogen, halogen, Ci-C ⁇ -alkyl, Ci-C ⁇ -alkoxy, C 3 -C 8 cycloalkyl;
• R 7 cyclic ring system with 3 - 14 ring atoms, which is optionally substituted by Ci-C ⁇ -alkyl, Ci-C ⁇ - alkoxy, Ci-C ⁇ -haloalkyl, Ci-C ⁇ -haloalkoxy, halogen; or Ci-C ⁇ -alkyl which is substituted by a cyclic ring system;
• n 0, 1 or 2;
• R 8 C ⁇ -C 6 -alkyl, C 6 haloalkyl, C! -C 6 alkoxy- C 2 -C 6 al yl, C 3 -C 6 alkenyl or C 3 -C 6 alkynyl;
• R 9 is hydrogen, Ci-C ⁇ -alkyl, C ⁇ -C 6 haloalkyl, C ⁇ -C 6 -alkoxy-C 2 -C 6 alkyl, C 3 -C 6 alkenyl or C 3 -C 6 alkynyl;
• R 10 is hydrogen or -CC 6 alkyl
• R 12 is hydrogen, Ci-C ⁇ -alkyl, C 3 -C 6 cycloalkyl,
• Ci-C ⁇ -haloalkyl C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, penyl or benzyl, where the latter two radicals can be partially or completely halogenated and / or carry one to three radicals from the following group can:
• R 13 is hydrogen, Ci-C ⁇ -alkyl, C 3 -C 6 -Al enyl or C 3 -C 6 ⁇ alkynyl; or
• R 12 and R 13 together form a C 2 -C 6 -alkanediyl chain which is mono- to tetrasubstituted by C ⁇ -C4 alkyl may be substituted and / or interrupted by oxygen or sulfur or an optionally C ⁇ -C4 ⁇ alkyl substituted nitrogen can be;
• R 14 is hydrogen, Ci-C ⁇ - alkyl, Ci-C ⁇ -haloalkyl,
• R 15 C ⁇ -C 6 -alkyl, C 6 haloalkyl, C 3 -C 6 cycloalkyl,
• the invention also relates to processes for the preparation of compounds of the formula I, compositions which contain them, and to the use of the compounds of the formula I and compositions containing them for controlling harmful plants.
• Herbicidal active ingredients from the class of benzoylpyrazoles are known from EP-A 282 944; WO 98/42677; WO 98/45273; WO98 / 50366; WO 98/52926; WO 98/56766; US 5,807,806.
• compositions which comprise the compounds I.
• processes for the preparation of these compositions and processes for controlling or reducing undesired plant growth with the compounds I were found.
• the present invention also relates to stereoisomers of the compounds of the formula I. Both pure stereoisomers and mixtures thereof are covered.
• the compounds of the formula I contain a carbon-carbon double bond and are therefore present as E isomers or Z isomers or as E / Z isomer mixtures.
• the compounds of the formula I can furthermore contain further carbon or carbon-nitrogen double bonds.
• the invention relates to both the pure geometric isomers and mixtures thereof.
• the compounds of the formula I can also 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 tautomers or as a mixture of tamers.
• the tautomeric forms result in particular from the hydroxy substituent on Pyrazole.
• the compounds can be referred to both as 5-hydroxypyrazoles or as 5-oxopyrazolines.
• 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.
• 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 are suitable.
• the cations used are in particular ions of the alkali metals, preferably lithium, sodium and potassium, the alkaline earth metals, preferably calcium and magnesium, and the transition metals, preferably manganese, copper, zinc and iron, and ammonium, where one to four hydrogen atoms by C ⁇ - C 4 alkyl or hydroxy -CC 4 alkyl and / or a phenyl or benzyl can be replaced, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri (C ⁇ -C 4 alkyl) - sulfonium and sulfoxonium ions, preferably tri (-C 4 alkyl) sulfoxonium, into consideration.
• the alkali metals preferably lithium, sodium and potassium
• the alkaline earth metals preferably calcium and magnesium
• Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of C 1 -C 4 -alkane acids, preferably formate, acetate Propionate and butyrate.
• the organic molecule parts mentioned for the substituents R i -R 16 represent collective terms for individual lists of the individual group members. All hydrocarbon chains, that is to say all alkyl, haloalkyl, cycloalkyl, alkoxyalkyl, alkoxy, haloalkoxy, cycloalkoxy, Alkyl hio, alkylsulfonyl, haloalkylsulfonyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, alkenyl, cycloalkenyl, alkynyl, alkenyloxy, alkynyloxy parts can be straight-chain or branched. Unless otherwise stated, halogenated substituents preferably have one to five identical or different halogen atoms. Halogen is fluorine, chlorine, bromine or iodine.
• C 2 -C 4 alkyl ethyl, n-propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl or 1, 1-dimethylethyl;
• C 2 -C 6 alkyl and the alkyl parts of, for example, -C 6 alkoxy-C 2 -C 6 alkyl: C 2 -C 4 alkyl, as mentioned above, and pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2, 2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1,3-dimethylbutyl, 2, 2-dimethylbutyl, 2, 3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-tri- methylpropyl, 1-ethyl-l-methylpropyl or l-ethyl-3-methyl
• Ci-Ce-alkyl as well as the alkyl parts of, for example, Ci-C ⁇ -alkoxy-Ci-Ce alkyl and -CC 6 alkylcarbonyl: C 2 -C 6 alkyl, as mentioned above, and methyl;
• C ⁇ ⁇ C 4 -haloalkyl a C ⁇ -C 4 -alkyl radical as mentioned above which, chlorine, bromine / or iodine partially or fully substituted by fluorine, and is substituted, 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 and the alkoxy parts of -C -C 4 alkoxycarbonyl: methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1, 1-dimethylethoxy; Ci-C ⁇ -alkoxy, and the alkoxy parts of -C-C6-alkoxy-C ⁇ -C6 _ alkyl, C ⁇ -C 6 -alkoxy-C 2 -C 6 -alkyl and C ⁇ -C 6 ⁇ alkoxycarbonyl: C 1 -C 4 - Alkoxy as mentioned above, and 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,
• C ⁇ -C 4 -haloalkoxy a C ⁇ -C 4 alkoxy radical as mentioned above which is partially or fully substituted by fluorine, iodine, chlorine, bromine and / or substituted, eg fluoromethoxy,
• Ci-C ⁇ -haloalkoxy C ⁇ -C 4 -haloalkoxy, as mentioned above, as well as, for example, 5-fluoropentoxy, 5-chloropentoxy, 5-bromogenoxy, 5-iodopentoxy, undecafluoropentoxy, 6-fluorohexoxy, 6-chlorohexoxy, 6- Bromhexoxy, 6-iodohexoxy or dodecafluorhexoxy;
• Ci-C ⁇ - alkylthio e.g. methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1, 1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3- Methylbutylthio, 2, 2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1, 1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1, 1-dimethylbutylthio, 1, 2-dimethylbutylthio, 1, 3-dimethylbutylthio, 2, 2-dimethylbutylthio, 2, 3-dimethylbutylthio
• Ci-C ⁇ -haloalkylsulfonyl a -CC 6 alkylsulfonyl, as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, that is fluoromethylsulfonyl, difluoromethylsulfonyl, trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl, bromodifonyl 2-fluoroethylsulfonyl, 2-chloroethylsulfonyl, 2-bromoethylsulfonyl, 2-iodoethylsulfonyl, 2, 2-difluoroethylsulfonyl, 2, 2, 2-trifluoroethylsulfonyl, 2,2, 2-trichloroethylsulfonyl, 2-chloro-2-fluoroethylsulfonyl
• C 3 -C 6 alkenyl prop-1-en-l-yl, prop-2-en-l-yl, 1-methylethenyl, buten-1-yl, buten-2-yl, buten-3- yl, 1-methyl-prop-1-en-l-yl, 2-methyl-prop-l-en-l-yl, l-methyl-prop-2-en- 1-yl, 2-methyl-prop-2-en-l-yl, penten-1-yl, penten-2-yl, penten-3-yl, penten-4-yl, 1-methyl-but-l- en-l-yl, 2-methyl-but-1-en-l-yl, 3-methyl-but-l-en-l-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
• C 3 -C 6 alkenyloxy e.g. B. Prop-1-en-l-yloxy, prop-2-en-l-yloxy, 1-methylethenyloxy, buten-1-yloxy, buten-2-yloxy, buten-3-yl-oxy, 1-methyl-prop- l-en-l-yloxy, 2-methyl-prop-l-en-l-yloxy, l-methyl-prop-2-en-l-yloxy, 2-methyl-prop-2-en-l-yloxy, Penten-1-yloxy, penten-2-yloxy, penten-3-yloxy, penten-4-yl - oxy, 1-methyl-but-l-en-l-yloxy, 2-methyl-but-l-en- l-yloxy,
• C 3 -C 6 alkynyl prop-1-in-1-yl, prop-2-in-1-yl, but-1-in-1-yl, but-1-in-3-yl, but- l-in-4-yl, but-2-in-l-yl, pent-1-in-l-yl, pent-l-in-3-yl, pent-l-in-4-yl, pent l-in-5-yl, pent-2-in-l-yl, pent-2-in-4-yl, pent-2-in-5-yl, 3-methyl-but-l-in-3- yl, 3-methyl-but-l-in-4-yl, hex-1-in-l-yl, hex-l-in-3-yl, hex-l-in-4-yl, hex-l- in-5-yl, hex-1-in-6-yl, hex-2-in-1-yl, hex-2-in-4-yl, hex
• C 2 -C 6 alkynyl C 3 -C 6 alkynyl, as mentioned above, and ethynyl:
• Cs-C ⁇ -alkynyloxy for example prop-1-in-1-yloxy, prop-2-in-1-yloxy, but-1-in-1-yloxy, but-1-in-3-yloxy, but-1 -in-4-yloxy, but-2-in-1-yloxy, pent-1-in-1-yloxy, pent-1-in-3-yloxy, pent-1-in-4-yloxy, pent-1 -in-5-yloxy, pent-2-in-1-yloxy, pent-2-in-4-yloxy, pent-2-in-5-yloxy, 3-methyl-but-l-in-3-yloxy , 3-methyl-but-1-in-4-yloxy, hex-1-in-1-yloxy, hex-1-in-3-yloxy, hex-1-in-4-yloxy, hex-1-in -5-yloxy, hex-1-in-6-yloxy, hex-2-in-1-yloxy,
• C 3 -C 6 cycloalkyl cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;
• C 3 -C 6 cycloalkoxy cyclopropoxy, cyclobutoxy, cyclopentoxy or cycloexoxy;
• C 3 -C 6 cycloalkenyl cyclopropen-1-yl, cyclobuten-1-yl, cyclobutenen-3-yl, cyclopenten-1-yl, cyclopenten-3-yl, cyclohexen-1-yl, cyclohexene 3-yl or cyclohexen-4-yl;
• Hetaryl, as well as the hetaryl residues in hetaryloxy and hetaryl -CC-C 4 ⁇ alkyl aromatic mono- or polycyclic residues which, in addition to carbon ring members, also contain one to four nitrogen atoms or one to three nitrogen atoms and one oxygen or one sulfur atom or one oxygen or one May contain sulfur atom, for example 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5 -Isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1
• C 2 -C 6 alkanediyl for example ethane-1, 2-diyl, propane-1, 3-diyl, butane-1, 4-diyl, pentane-1, 5-diyl or hexane-1, 6-diyl;
• C 3 -C 8 cycloalkyl in particular C 3 -C6 cycloalkyl as mentioned above, furthermore
• Carbocyclic bi- or tricyclic ring systems are for example adamantyl, norbornyl, camphyl or camphenyl.
• the bi- or tricyclic ring systems can optionally be substituted by Ci-C ⁇ -alkyl, Ci-C ⁇ -alkoxy,
• Ci-C ⁇ -haloalkyl, -CC 6 -haloalkoxy or halogen be substituted one or more times.
• Ci-C ⁇ -alkyl which is substituted by a cyclic ring system with 3 - 14 ring atoms: a straight-chain or branched Ci-C ⁇ -alkyl group which is characterized by the aforementioned C 3 -C 6 cycloalkyl, C 3 -C 6 - Cycloalkenyl groups or carbocyclic or heterocyclic ring systems with up to 14 ring atoms is substituted. Examples include: cyclopropyl-methyl, 1-cyclopropyl-ethyl, 2-cyclopropyl-ethyl,
• ring systems optionally may be prepared by C ⁇ -C ö -alkyl, C 6 alkoxy, C ⁇ -C6-halo-alkyl, C ⁇ -C -haloalkoxy or halogen or mono- 6 be substituted multiple times.
• All phenyl, hetaryl and heterocyclyl rings are preferably unsubstituted or carry one to three halogen atoms and / or one or two radicals from the following group: nitro, cyano, methyl, trifluoromethyl, methoxy, trifluoromethoxy or methoxycarbonyl.
• the variables preferably have the following meanings, in each case individually or in combination with one another: Ri is nitro, halogen, cyano, thiocyanato, Ci-C ⁇ -alkyl, C 6 haloalkyl, C ⁇ -C 6 -alkoxy-C ⁇ -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 -Alkynyl, -OR 6 or -S (0) n R 8 ; in particular nitro, fluorine, chlorine, bromine, methyl, ethyl, methoxy; preferably chlorine, methyl or methoxy.
• R2 is hydrogen, nitro, halogen, cyano, thiocyanato, C ⁇ -C 6 -alkyl, C 6 haloalkyl, Ci-C ⁇ -alcohol xy-C ⁇ -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, -OR 6 or particularly preferably hydrogen, nitro, halogen, such as fluorine, chlorine or bromine, Ci-C ⁇ -alkyl, Ci-C ⁇ -haloalkyl, -OR 6 or -S0R 8 ; in particular nitro, halo such as fluorine, chlorine or bromine, C ⁇ -C 6 -alkyl, C 6 haloalkyl, -OR 6, or S0 2 R 8; preferably -S0 2 -R 8 , where R 8 is Ci-C ⁇ -alkyl, especially methyl or ethyl.
• the substituent R 2 is preferably in the 4- or 5-position of the phen
• R 3 is hydrogen, halogen, Ci-C ⁇ -alkyl, -C-C 6 haloalkyl, Ci-C ⁇ -alkoxy, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl; particularly preferably hydrogen, halogen such as
• R 4 is hydrogen, nitro, halogen, cyano, rhodano,
• R6 is hydrogen, methyl; especially hydrogen.
• R 7 cyclopropyl, cyclopentyl, cyclohexyl, adamantyl,
• Ci-C ⁇ -alkyl especially methyl.
• R 8 Ci-C ö alkyl, especially methyl, ethyl
• R 9 is hydrogen, -CC 6 alkyl
• R 12 is hydrogen, Ci-C ⁇ -alkyl
• R 3 is hydrogen, C ⁇ -C 6 alkyl
• R 14 is hydrogen, -CC 6 alkyl
• Ri5 hydrogen, C ⁇ -C 6 alkyl, -CC 6 alkoxy.
• R 16 hydroxy.
• R 1 -R 15 each independently have the following meanings:
• R 4 is hydrogen
• R 5 is hydrogen
• R 6 is hydrogen
• R 7 cyclopropyl, cyclopentyl, adamantyl, norbornyl, camphyl or camphenyl, which are unsubstituted or mono- or disubstituted by methyl.
• R 1 -C 6 alkyl; Halogen; C ⁇ -C 6 alkoxy.
• R 2 Ci-C ß- alkylsulfonyl; where R 2 is preferably in the para position to the pyrazolylcarbonyl group on the phenyl ring.
• R 5 hydrogen or -CC 6 alkyl
• R 7 cyclopropyl, cyclopentyl.
• R 16 hydroxy or phenylsulfonyloxy
• Preferred embodiments are the following compounds of the formulas Ial-Ia6:
• compounds Ia2 in particular the compounds Ia2.001-Ia2.018, which differ from the corresponding compounds Ial .001-Ial .018 in that R 5 in formula I is methoxy:
• compounds Ia3 in particular the compounds Ia3.001-la3.018, which differ from the corresponding compounds Ial .001-Ial.018 in that R 5 in formula I is methyl:
• compounds Ia6 in particular the compounds Ia6.001-Ia6.018, which differ from the corresponding compounds Ial .001-Ial.018 in that R 5 in formula I is i-propyl:
• the compounds of the formula I are essentially prepared by the processes described in WO 98/50366.
• R 7 with a carboxylic acid III or an activated derivative thereof
• variables R 1 to R 5 have the meanings given in claim 1 and L 1 represents hydroxyl or a nucleophilically displaceable leaving group (for example halogen, anhydride), acylated and the acylation product rearranged to the compounds I, if appropriate in the presence of a catalyst.
• L 1 represents hydroxyl or a nucleophilically displaceable leaving group (for example halogen, anhydride), acylated and the acylation product rearranged to the compounds I, if appropriate in the presence of a catalyst.
• the compounds I can be in the form of their agriculturally useful salts, the type of salt generally not being important. Usually the salts of such bases will be considered which do not adversely affect the herbicidal activity of I.
• Particularly suitable basic salts are those of the alkali metals, preferably the lithium, sodium and potassium salts, those of the alkaline earth metals, preferably calcium, magnesium and barium salts and those of the transition metals, preferably manganese, copper, zinc and iron salts, ammonium salts , and ammonium salts which can carry one to four C ⁇ -C 4 alkyl, hydroxy-C ⁇ -C 4 alkyl substituents, a phenyl or benzyl substituent, preferably diethylammonium, diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium -, And trimethyl (2-hydroxyethyl) ammonium salts, the phosphonium salts, the sulfonium salts, preferably tri- (C 4 -C 4 -alkyl) sulfonium salts, and the sulfoxonium salts, preferably tri- (
• the compounds I and their agriculturally useful salts are suitable - both as isomer mixtures and in the form of the pure isomers - as herbicides. They can also be used as growth regulators for plants (harmful plants, crops and useful plants).
• the herbicidal compositions containing the compounds I control vegetation on nonculture areas very good, especially with high application rates. 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 substances are less compatible for certain crop plants, application techniques can be used in which the herbicidal compositions are sprayed with the aid of sprayers in such a way that the leaves of the sensitive crop plants are not struck wherever possible, while the active compounds grow more rapidly on the leaves below 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, old-dispersions, pastes, dusts, sprays or granules , Dusting, scattering or pouring.
• the application forms depend on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.
• mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, also coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, alkylated benzenes or their derivatives, alcohols such as methanol, ethanol, propanol, butanol, cyclohexanol, ketones such as cyclohexanone or strongly polar solvents, e.g. B. amines such as N-methylpyrrolidone or water.
• mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, also coal tar oils and oils of vegetable or animal origin
• aliphatic, cyclic and aromatic hydrocarbons e.g. Paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, al
• Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water.
• the compounds I 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 octylp enol ether, ethoxylated isooctyl, octyl or nonylphenol, alkylphenol, alkylphenol
• 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, Urine and vegetable products such as cereal 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:
• I 20 parts by weight of a compound I are dissolved in a mixture consisting of 80 parts by weight of alkylated benzene, 10 parts by weight of the adduct of 8 to 10 mol of ethylene oxide and 1 mol of oleic acid-N-monoethanolamide, 5 parts by weight of calcium salt of dodecylbenzenesulfonic acid and 5 parts by weight of the adduct of 40 Moles of ethylene oxide to 1 mole of castor oil.
• aqueous dispersion is obtained which contains 0.02% by weight of the active ingredient.
• V 3 parts by weight of an active ingredient of the formula I 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 a compound I 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.
• 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 come as mixing partners -l, 3-cyclohexanediones, hetaryl aryl ketones, benzylisoxazolidinones, meta-CF3-phenyl derivatives, carbamates, quinoline carboxylic acid 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, urine substances, 3-
• the active compound application rates are 0.001 to 3.0, preferably 0.01 to 1.0 kg / ha of active substance (see also)
• Plastic pots with loamy sand with about 3.0% humus as substrate served as culture vessels.
• the seeds of the test plants were sown separately according to 2 types.
• the active ingredients suspended or emulsified in water were applied directly after sowing using finely distributing nozzles.
• the tubes were lightly sprinkled to promote "germination and growth, and then covered with transparent plastic hoods until the plants had grown. This cover causes the test plants to germinate evenly, unless this was affected by the active ingredients.
• test plants were first grown to a height of 3 to 15 cm 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 trial period lasted 2 to 4 weeks. During this time, the plants were cared for and their response to each treatment was evaluated.
• Evaluation is based 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 preferably composed of the following types:

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  • 2000-06-23 EP EP00945814A patent/EP1194407A2/de not_active Withdrawn
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