Benzazolonylcarbonylcyclohexenones and their use ss herbicides

A cyclohexenone derivative of a benzazolone of the formula I

• 92
• in which A, R1, R2, R3 and Hex are as defined below:
• A is O, S, SO, SO2 or NR6;
• R1 is halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-hydroxyalkyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-haloalkoxy-C1-C4-alkyl, C1-C4-haloalkylthio-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl, C1-C4-alkylsulfonyl-C1-C4-alkyl, C1-C4-haloalkylsulfonyl-C1-C4-alkyl, C1-C4-alkoxy, C1-C4-hydroxyalkoxy, C1-C4-haloalkoxy, C1-C4-alkoxy-C1-C4-alkoxy, C1-C4-haloalkoxy-C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl;
• R2 is hydroxyl, nitro, amino, C1-C6-alkylamino, di(C1-C6-alkyl)amino, cyano, CHO, C1-C6-alkoxy, C1-C6-alkyl, C1-C6-hydroxyalkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-haloalkoxy-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C1-C6-haloalkoxy-C2-C6-alkenyl, C1-C6-alkoxy-C2-C6-alkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-haloalkoxy-C2-C6-alkynyl, C1-C6-alkoxy-C2-C6-alkynyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, (C1-C6-alkyl)carbonyl, C1-C6-haloalkylcarbonyl, hydroxycarbonyl-C1-C4-alkyl, C1-C6-alkoxycarbonyl-C1-C6-alkyl,
• a radical of the formula C(O)OR4, CON(R5)2 or C(═NOR4a)R4b, aryl, aryl-C1-C4-alkyl, arylsulfonyl, arylcarbonyl, C3-C6-cycloalkyl, C3-C6-cycloalkenyl, 3-, 4-, 5-, 6- or 7-membered heterocyclyl, 3-, 4-, 5-, 6- or 7-membered heterocyclyl-C1-C6-alkyl, where each aryl, cycloalkyl, cycloalkenyl and each heterocyclyl radical may be unsubstituted or may carry one, two, three or four substituents, in each case selected from the group consisting of halogen, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy;
• R3 is hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-haloalkoxy-C1-C4-alkyl or halogen;
• in which
• R4 is C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-haloalkoxy-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C1-C6-haloalkoxy-C2-C6-alkenyl, C1-C6-alkoxy-C2-C6-alkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-haloalkoxy-C2-C6-alkynyl, C1-C6-alkoxy-C2-C6-alkynyl;
• R4a, R4b independently of one another may have the meanings mentioned for R4, and R4b may be hydrogen;
• R5 independently of one another are hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, (C1-C6-haloalkoxy)-C1-C6-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C1-C6-haloalkyl-C2-C6-alkenyl, C1-C6-haloalkoxy-C2-C6-alkenyl, C1-C6-alkoxy-C2-C6-alkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C1-C6-haloalkyl-C2-C6-alkynyl, C1-C6-haloalkoxy-C2-C6-alkynyl, C1-C6-alkoxy-C2-C6-alkynyl, or together form a 3- to 7-membered heterocycle which may be partially or fully halogenated and/or may carry one, two or three substituents selected from the group consisting of C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy;
• R6 is hydrogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-haloalkoxy-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkyl;
• and
• Hex is substituted (3-oxo-1-cyclohexen-2-yl)carbonyl of the formula IIa or substituted (1,3-dioxo-2-cyclohexyl)methylidene of the formula IIb,
• 93
• in which the variables R7 to R13 are as defined below:
• R7 is hydroxyl, mercapto, halogen, OR14, SR14, SOR15, SO2R15, OSO2R15, P(O)R16R17, OP(O)R16R17, P(S)R16R17, OP(S)R16R17, NR18R19, ONR18R19 or N-bonded heterocyclyl which may be partially or fully halogenated and/or may carry one to three of the following radicals:
• nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
• R8, R12 independently of one another are hydrogen, C1-C4-alkyl or C1-C4-alkoxycarbonyl;
• R9, R11, R13 independently of one another are hydrogen or C1-C4-alkyl;
• R10 is hydrogen, halogen, hydroxyl, C1-C6-alkyl, C1-C6-haloalkyl, di-(C1-C6-alkoxy)-methyl, (C1-C6-alkoxy)-(C1-C6-alkylthio)methyl, di-(C1-C6-alkylthio)methyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-C6-haloalkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-haloalkylsulfonyl, C1-C6-alkoxycarbonyl, C1-C6-haloalkoxycarbonyl;
• is 1,3-dioxolan-2-yl, 1,3-dioxan-2-yl, 1,3-oxathiolan-2-yl, 1,3-oxathian-2-yl, 1,3-dithiolan-2-yl or 1,3-dithian-2-yl, where the six lastmentioned radicals may be substituted by one to three C1-C4-alkyl radicals;
• or
• R9 and R11 or R11 and R13 together form a n bond or a C1-C5-alkylene chain which may carry one, two or three radicals from the following group:
• halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxycarbonyl;
• or
• R9 and R13 together form a C1-C4-alkyl chain which may carry one, two or three radicals from the following group:
• halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxycarbonyl;
• or
• R10 and R11 together form a —O—(CH2)p—O—, —O—(CH2)p—S—, —S—(CH2)p—S—, —O—(CH2)q— or —S—(CH2)q— chain, in which p is 2, 3, 4 or 5 and q is 2, 3, 4, 5 or 6, which may be substituted by one, two or three radicals from the following group:
• halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxycarbonyl;
• or
• R10 and R11, together with the carbon to which they are attached, form a carbonyl group;
• where
• R14 is C1-C6-alkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkynyl, C3-C6-haloalkynyl, C3-C6-cycloalkyl, C1-C6-alkylcarbonyl, C2-C6-alkenylcarbonyl, C2-C6-alkynylcarbonyl, C3-C6-cycloalkylcarbonyl, C1-C6-alkoxycarbonyl, C3-C6-alkenyloxycarbonyl, C3-C6-alkynyloxycarbonyl, C1-C6-alkylthiocarbonyl, C1-C6-alkylaminocarbonyl, C3-C6-alkenylaminocarbonyl, C3-C6-alkynylaminocarbonyl, N,N-di(C1-C6-alkyl)aminocarbonyl, N-(C3-C6-alkenyl)-N-(C1-C6-alkyl) aminocarbonyl, N-(C3-C6-alkynyl)-N-(C1-C6-alkyl)aminocarbonyl, N-(C1-C6-alkoxy)-N-(C1-C6-alkyl)aminocarbonyl, N-(C3-C6-alkenyl)-N-(C1-C6-alkoxy)aminocarbonyl, N-(C3-C6-alkynyl)-N-(C1-C6-alkoxy)aminocarbonyl, di (C1-C6-alkyl) aminothiocarbonyl, C1-C6-alkoxyimino-C1-C6-alkyl, where the alkyl, cycloalkyl and alkoxy radicals mentioned may be. partially or fully halogenated and/or may carry one, two or three of the following groups:
• cyano, C1-C4-alkoxy, C1-C4-alkylthio, di(C1-C4-alkyl)amino, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, C1-C4-alkoxy-C1-C4-alkoxycarbonyl, hydroxycarbonyl, C1-C4-alkylaminocarbonyl, di(C1-C4-alkyl)aminocarbonyl, aminocarbonyl, C1-C4-alkylcarbonyloxy or C3-C6-cycloalkyl;
• is phenyl, phenyl-C1-C6-alkyl, phenylcarbonyl-C1-C6-alkyl, phenylcarbonyl, phenoxycarbonyl, phenoxythiocarbonyl, phenylaminocarbonyl, N-(C1-C6-alkyl)-N-phenylaminocarbonyl, phenyl-C2-C6-alkenylcarbonyl, heterocyclyl, heterocyclyl-C1-C6-alkyl, heterocyclylcarbonyl-C1-C6-alkyl, heterocyclylcarbonyl, heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl, heterocyclylaminocarbonyl, N-(C1-C6-alkyl)-N-heterocyclylaminocarbonyl, or heterocyclyl-C1-C6-alkenylcarbonyl, where the phenyl and the heterocyclyl radical of the 18 lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals:
• nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
• R15 is C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl or C3-C6-cycloalkyl, where the four radicals mentioned may be partially or fully halogenated and/or may carry one, two or three of the following groups:
• cyano, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl or C1-C4-haloalkoxycarbonyl;
• is phenyl, phenyl-C1-C4-alkyl, heterocyclyl or heterocyclyl-C1-C4-alkyl, where the phenyl and the heterocyclyl radical of the four lastmentioned substituents may be partially or fully halogenated and/or may carry one, two or three of the following radicals:
• nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkoxycarbonyl;
• R16, R17 independently of one another are hydrogen, hydroxyl, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkylthio, phenyl, phenyl-C1-C4-alkyl or phenoxy, where the three lastmentioned substituents may be partially or fully halogenated and/or may carry one, two or three of the following radicals:
• nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkoxycarbonyl;
• R18 is hydrogen, C1-C6-alkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkynyl, C3-C6-haloalkynyl, C3-C6-cycloalkyl, C1-C6-alkylcarbonyl, hydroxyl, C1-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, amino, C1-C6-alkylamino, di(C1-C6-alkyl)amino or C1-C6-alkylcarbonylamino, where the alkyl, cycloalkyl or alkoxy radicals mentioned may be partially or fully halogenated and/or may carry one, two or three of the following radicals:
• cyano, C1-C4-alkoxycarbonyl, C1-C4-alkylaminocarbonyl, di(C1-C4-alkyl)-aminocarbonyl or C3-C6-cycloalkyl;
• is phenyl, phenyl-C1-C4-alkyl, phenylcarbonyl, heterocyclyl, heterocyclyl-C1-C4-alkyl or heterocyclylcarbonyl, where the phenyl or heterocyclyl radical of the six lastmentioned substituents may be partially or fully halogenated and/or may carry one to three of the following radicals:
• nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
• R19 is hydrogen, C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl;
• and its agriculturally useful salts.