Isoxazolyl- and isoxazolinyl-substituted benzoylcyclohexanediones, process for their preparation and their use as herbicides and plant growth regulators

An isoxazolyl- or isoxazolinyl-substituted benzoylcyclohexanedione of the formula (I),

• in which
• A is a saturated or mono- or polyunsaturated hydrocarbon chain comprising one to eight carbon atoms as chain members, which is optionally substituted by one or more radicals from the group consisting of halogen, C1-C6-alkyl, C1-C6-alkoxy and hydroxyl and which is optionally interrupted by one or two divalent radicals from the group consisting of oxygen, sulfur and carbonyl;
• R1 is OR11, SR11, SOR11, SO2R11, CO2R8, CONR8R9, N(R8)COR9, N(R8)SO2R9, N(R8)—CO—X, P(O)R8R9, cyano, nitro, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, phenyl, phenoxy, phenylthio, heteroaryl, heteroaryloxy, heterocyclyl or heterocyclyloxy, where the nine last-mentioned radicals are optionally mono- or polysubstituted, or
• A and R1 together form a radical of the group consisting of heteroaryl and heterocyclyl, where these two mentioned radicals are optionally mono- or polysubstituted;
• Ra, Rb, Rc independently of one another are hydrogen, optionally mono- or polysubstituted C1-C9-alkyl, OR11, SR11, SOR11, SO2R11, CONH2, CONR8R9,11, cyano, nitro, halogen or the group A—R1, or
• Ra and Rc together form a bond;
• R2, is R3, R4 and R5 independently of one another are hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, aryl, arylalkyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocyclylalkyl, hydroxyl, alkoxy, cycloalkoxy, aryloxy, heteroaryloxy, heterocyclyloxy, alkylthio, arylthio, heteroarylthio, heterocyclylthio, heterocyclylalkylthio, amino, mono- or dialkylamino, mono- or diarylamino, N-alkyl-N-arylamino, cycloalkylamino, alkylsulfonyl, arylsulfonyl, alkylsulfinyl, aminosulfonyl, mono- or dialkylaminosulfonyl, mono- or diarylaminosulfonyl, N-alkyl-N-arylaminosulfonyl, N-alkyl-N-heteroarylaminosulfonyl, alkylsulfonylamino, cycloalkylsulfonylamino, arylsulfonylamino, heteroarylsulfonylamino, cycloalkylsulfonyl-N-alkylamino, arylsulfonyl-N-alkylamino, heteroarylsulfonyl-N-alkylamino, heterocyclylsulfonyl-N-alkylamino, alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, arylalkylcarbonyl, heteroarylcarbonyl, heterocyclylcarbonyl, carboxyl, alkoxycarbonyl, aryloxycarbonyl, arylalkoxycarbonyl, alkylcarbonyloxy, arylcarbonyloxy, arylalkylcarbonyloxy, aminocarbonyl, mono- or dialkylaminocarbonyl, N-alkyl-N-arylaminocarbonyl, N-alkyl-N-heteroarylaminocarbonyl, N-alkyl-N-arylaminocarbonyloxy, aminocarbonylamino, mono- or dialkylaminocarbonylamino, mono- or diarylaminocarbonylamino, mono- or diheteroarylaminocarbonylamino, N-alkyl-N-arylaminocarbonylamino, mono- or dialkylcarbonylamino, mono- or diarylcarbonylamino, alkylcarbonyl-N-arylamino, arylcarbonyl-N-alkylamino, alkoxycarbonyloxy, cycloalkoxycarbonyloxy, aryloxycarbonyloxy, arylalkoxycarbonyloxy, alkoxycarbonylamino, cycloalkoxycarbonylamino, aryloxycarbonylamino, alkoxycarbonyl-N-alkylamino, formyl, halogen, haloalkyl, haloalkenyl, haloalkynyl, haloalkoxy, haloalkenyloxy, haloalkynyloxy, haloalkylthio, haloalkenylthio, haloalkynylthio, haloalkylamino, haloalkenylamino, haloalkynylamino, haloalkylsulfonyl, haloalkenylsulfonyl, haloalkynylsulfonyl, haloalkylsulfinyl, haloalkenylsulfinyl, haloalkynylsulfinyl, haloalkylcarbonyl, haloalkenylcarbonyl, haloalkynylcarbonyl, haloalkoxycarbonyl, haloalkenyloxycarbonyl, haloalkynyloxycarbonyl, haloalkylaminocarbonyl, haloalkenylaminocarbonyl, haloalkynylaminocarbonyl, haloalkoxycarbonylamino, haloalkylaminocarbonylamino, cyano, nitro, arylalkoxyalkoxy or alkoxyalkoxyalkoxy;
• R6 is OR10, alkylthio, haloalkylthio, alkenylthio, haloalkenylthio, alkynylthio, haloalkynylthio, alkylsulfinyl, haloalkylsulfinyl, alkenylsulfinyl, haloalkenyisulfinyl, alkynylsulfinyl, haloalkynylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkenylsulfonyl, haloalkenylsulfonyl, alkynylsulfonyl, haloalkynylsulfonyl, optionally substituted phenylthio, cyano, cyanato, thiocyanato or halogen;
• R7 is hydrogen, tetrahydropyran-3-yl, tetrahydropyran4-yl, tetrahydrothiopyran-3-yl, alkyl, cycloalkyl, alkoxy, alkoxyalkyl, alkylcarbonyl, alkoxycarbonyl, alkylthio, phenyl, where the eight last-mentioned groups are optionally substituted by one or more, identical or different radicals from the group consisting of halogen, alkylthio and alkyloxy, or
• two radicals R7 bonded to a common carbon atom form a chain from the group consisting of OCH2CH2O, OCH2CH2CH2O, SCH2CH2S and SCH2CH2CH2S, this optionally being substituted by one to four methyl groups, or
• two radicals R7 bonded to directly adjacent carbon atoms form a bond or, with the carbon atoms carrying them, form a 3- to 6-membered ring optionally substituted by one or more, identical or different radicals from the group consisting of halogen, alkyl, alkylthio and alkoxy;
• R8 and R9 independently of one another are hydrogen, alkyl, alkyloxy, alkoxy, alkenyl, alkenyloxy, alkynyl, haloalkyl, cycloalkyl, cyanoalkyl, haloalkenyl, haloalkynyl, optionally substituted aryl or optionally substituted arylalkyl, or
• R8 and R9, together with the atom bonding them, form a 5- or 6-membered saturated, partially or completely unsaturated ring, which optionally contains one or two further heteratoms from the group consisting of oxygen and nitrogen and which is optionally substituted by one to three radicals from the group consisting of halogen, alkyl and oxo;
• R10 is hydrogen, alkyl, haloalkyl, alkoxyalkyl, formyl, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylsulfonyl, haloalkylsulfonyl, benzoyl or phenylsulfonyl, the two last-mentioned groups optionally being substituted by one or more, identical or different radicals from the group consisting of alkyl, haloalkyl, alkoxy, haloalkoxy, halogen, cyano and nitro;
• R11 is R10, alkenyl, alkynyl, cycloalkyl, cycloalkenyl or cycloalkylalkyl;
• X is a radical from the group consisting of heteroaryl and heterocyclyl;
• Y is a divalent radical from the group consisting of O, S, N—H, N-alkyl, CHR7 and C(R7)2;
• Z is a divalent radical from the group consisting of O, S, SO, SO2, N—H, N-alkyl, CHR7 and C(R7)2;
• v is 0 or 1;
• w is 0,1,2,3 or 4,
• with the proviso that at least two radicals from R2, R3, R4 and R5 are hydrogen.