Cyclohexenonquinolinoyl-derivatives as herbicidal agents

A cyclohexenonequinolinoyl compound of the formula I

• where:
• R1 is hydrogen, nitro, halogen, cyano, C1–C6-alkyl, C1–C6-haloalkyl, C1–C6-alkoxyiminomethyl, C1–C6-alkoxy, C1–C6-haloalkoxy, C1–C6-alkylthio, C1–C6-haloalkylthio, C1–C6-alkylsulfinyl, C1–C6-haloalkylsulfinyl, C1–C6-alkylsulfonyl, C1–C6-haloalkylsulfonyl, aminosulfonyl, N—(C1–C6-alkyl)aminosulfonyl, N, N-di-(C1–C6-alkyl) aminosulfonyl N—(C1–C6-alkylsulfonyl)amino, N—(C1–C6-haloalkylsulfonyl)amino, N—(C1–C6-alkyl)-N-(C1–C6-alkylsulfonyl)amino, N—(C1–C6-alkyl)-N-(C1–C6-haloalkylsulfonyl)amino, phenoxy, or phenylthio the four last-mentioned radicals may be partially or fully halogenated and/or may carry one to two of the following substituents:
• nitro, cyano, C1–C4-alkyl, C1–C4-haloalkyl, C1–C4-alkoxy or C1–C4-haloalkoxy;
• R2, R3 are hydrogen, C1–C6-alkyl, C1–C6-haloalkyl or halogen;
• R4 is a compound IIa or IIb
• where
• R5 is halogen, OR7, SR7, SOR8, SO2R8, OSO2R8, POR8R9, OPR8R9, OPOR8R9, OPSR8R9, NR10R11, ONR11R12
• R6 is nitro, halogen, cyano, C1–C6-alkyl, C1–C6-haloalkyl, di-(C1–C6-alkoxy)methyl, di-(C1–C6-alkylthio)methyl, (C1–C6-alkoxy)(C1–C6-alkylthio)methyl, hydroxyl, C1–C6-alkoxy, C1–C6-haloalkoxy, C1–C6-alkoxycarbonyloxy, C1–C6-alkylthio, C1–C6-haloalkylthio, C1–C6-alkylsulfinyl, C1–C6-haloalkylsulfinyl, C1–C6-alkylsulfonyl, C1–C6-haloalkylsulfonyl, C1–C6-alkylcarbonyl, C1–C6-haloalkylcarbonyl, C1–C6-alkoxycarbonyl or C1–C6-haloalkoxycarbonyl;
• or
• two radicals, which are linked to the same carbon, together form an —O—(CH2)m—O—, —O—(CH2)m—S—, —S—(CH2)m—S—, —O—(CH2)n— or —S—(CH2)n chain which is unsubstituted or substituted by one to three radicals from the following group:
• halogen, cyano, C1–C4-alkyl, C1–C4-haloalkyl or C1–C4alkoxycarbonyl;
• or
• two radicals, which are linked to the same carbon, together form a —(CH2)p chain which possibly is interrupted by oxygen or sulfur and/or is unsubstituted or substituted by one to four radicals from the following group:
• halogen, cyano, C1–C4-alkyl, C1–C4-haloalkyl or C1–C4alkoxycarbonyl;
• or
• two radicals, which are linked to the same carbon, together form a methylidene group which is unsubstituted or substituted by one or two radicals from the following group:
• halogen, hydroxyl, formyl, cyano, C1–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 or C1–C6-haloalkylsulfonyl;
• or
• two radicals, which are linked to the same carbon, together with this carbon form a carbonyl group;
• or
• two radicals, which are linked to different carbons, together form a —(CH2)n chain which is unsubstituted or substituted by one to three radicals from the following group:
• halogen, C1–C6-alkyl, C1–C6-alkoxy, hydroxyl or C1–C6-alkoxycarbonyl;
• R7 is C1–C6-alkyl, C3–C1-alkenyl, C3–C6-haloalkenyl, C3–C6-alkynyl, C3–C6-haloalkynyl, C3–C6-cyloalkyl, C1–C20-alkylcarbonyl, C2–C6-alkenylcarbonyl, C2–C6-alkynylcarbonyl, C3–C6-cyloalkylcarbonyl, C1–C6-alkoxycarbonyl, C3–C6-alkenyloxycarbonyl, C3–C6-alkynyloxycarbonyl, (C1–C20-alkylthio)carbonyl, 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–C6alkynyl)-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-alkylcarbonyl-C1–C6-alkyl, C1–C6-alkoxyimino-C1–C6-alkyl, N—(C1–C6-alkylamino) imino-C1–C6-alkyl or N,N-di-(C1–C6-alkylamino)imino-C1–C6-alkyl, it being possible for the above-mentioned alkyl, cycloalkyl and alkoxy radicals to be partially or fully halogenated and/or to carry one to 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, di-(C1–C4-alkyl)amino-C1–C4-alkoxycarbonyl, hydroxycarbonyl, C1–C4-alkylaminocarbonyl, di-(C1–C4-alkyl)aminocarbonyl, aminocarbonyl, C1–C4-alkylcarbonyloxy or C3–C6-cycloalkyl;
• phenyl, phenyl-C1–C6-alkyl, phenylcarbonyl-C1–C6-alkyl, phenylcarbonyl, phenoxycarbonyl, phenoxythiocarbonyl, phenoxy-C1–C1-alkylcarbonyl, phenylaminocarbonyl, N—(C1–C6-alkyl)-N-(phenyl)aminocarbonyl, or phenyl-C2–C8-alkenylcarbonyl, the phenyl radical of the 10 last-mentioned 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-halogenalkyl, C1–C4-alkoxy or C1–C4-haloalkoxy;
• R8,R9 are C1–C6-alkyl, C3–C6-alkenyl, C3–C6-haloalkenyl, C3–C6-alkynyl, C3–C6-haloalkynyl, C3–C6-cycloalkyl, hydroxyl, C1–C6-alkoxy, amino, C1–C6-alkylamino, C1–C6-haloalkylamino, di-(C1–C8-alkyl)amino or di-(C1–C6-haloalkyl)amino, it being possible for the abovementioned alkyl, cycloalkyl and alkoxy radicals to be partially or fully halogenated and/or to carry one to 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, di-(C1–C4-alkyl)amino-C1–C4-alkoxycarbonyl, hydroxycarbonyl, C1–C4-alkylaminocarbonyl, di-(C1–C4alkyl)aminocarbonyl, aminocarbonyl, C1–C4-alkylcarbonyloxy or C3–C6-cycloalkyl;
• phenyl, phenyl-C1–C-alkyl, phenoxy, the phenyl radical of the last-mentioned 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;
• R10 is C1–C6-alkyl, C3–C6-alkenyl, C3–C6-haloalkenyl, C3–C6-alkynyl, C3–C6-haloalkynyl, C3–C6-cycloalkyl, 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 abovementioned alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and/or may carry one to three radicals from the following group:
• cyano, C1–C4-alkoxy, C1–C4-alkylthio, di-(C1–C4-alkyl)amino, C1–C4-alkylcarbonyl, C1–C4-alkoxycarbonyl, C1–C4-alkoxy-C1–C4-alkoxycarbonyl, di-(C1–C4-alkyl)amino-C1–C4-alkoxycarbonyl, hydroxycarbonyl, C1–C4-alkylaminocarbonyl, di-(C1–C4-alkyl)aminocarbonyl, aminocarbonyl, C1–C4-alkylcarbonyloxy or C3–C6-cycloalkyl;
• phenyl, or phenyl-C1–C6-alkyl, where the phenyl radical of the two last-mentioned 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;
• R11,R12 are C1–C6-alkyl, C3–C6-alkenyl, C3–C6-alkynyl or C1–C6-alkylcarbonyl;
• l is 0 to 6;
• m is 2 to 4;
• n is 1 to 5;
• p is 2 to 5;
• and their agriculturally useful salts.