Cyclohexenonedioxothiochromanoyl derivatives

A cyclohexenonedioxothiochromanoyl derivative of the formula I

• where:
• X is oxygen, sulfur, S═O, S(═O)2, CR4R5, C═O or C═NR6;
• R1 is hydrogen, nitro, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haoalkylthio, 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 or N—(C1-C6-alkyl)-N—(C1-C6-haloalkylsulfonyl)amino;
• R2 is C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy;
• R3 is hydrogen, C1-C6-alkyl or halogen;
• R4, R5 are hydrogen, nitro, halogen, 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, C1-C6-haloalkylsulfonyl, N—C1-C6-alkylamino, N—C1-C6-haloalkylamino, N,N-di-(C1-C6-alkyl)amino, N—C1-C6-alkoxyamino, N—(C1-C6-alkoxy)-N—(C1-C6-alkyl)amino, 1-tetrahydropyrrolyl, 1-piperidinyl, 4-morpholinyl or 1-hexahydropyrazinyl;
• or
• R4 and R5 together form an —O—(CH2)m—O—, —O—(CH2)m—S—, —S—(CH2)m—S— or —O—(CH2)n— chain which may be substituted by one to three radicals selected from the following group:
• halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxycarbonyl;
• or
• R4 and R5 together form a —(CH2)p— chain which may be interrupted by oxygen or sulfur and/or may be substituted by one to four radicals selected from the following group:
• halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxycarbonyl;
• or
• R4 and R5 together form a methylidene group which may be substituted by one to two radicals selected from the following group:
• halogen, cyano, hydroxyl, formyl, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C1-C6-alkylsulfinyl, C1-6-haloalkylsulfinyl, C1-C6-alkylsulfonyl or C1-C6-haloalkylsulfonyl;
• R6 is C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy;
• l is 0 to 4;
• m is 2 to 4;
• n is 1 to 5;
• p is 2 to 5;
• R7 is a compound IIa or IIb
• where
• R8 is halogen, OR10, SR10, SOR11, SO2R11, OSO2R11, POR11R12, OPOR11R12, OPSR11R12, NR13R14, ONR14R14, N-bonded heterocyclyl or O—(N-bonded heterocyclyl), where the heterocyclyl radical of the two 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;
• R9 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-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 radical R9 which are attached to the same carbon together form an —O—(CH2)m—O—, —O—(CH2)m—S—, —S—(CH2)m—S— or —O—(CH2)n— chain which may be substituted by one to three radicals selected from the following group:
• halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxycarbonyl;
• or
• two radicals R9 which are attached to the same carbon together form a —(CH2)p— chain which may be interrupted by oxygen or sulfur and/or may be substituted by one to four radicals selected from the following group:
• halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxycarbonyl;
• or
• two radicals R9 which are attached to the same carbon together form a methylidene group which may be substituted by one to two radicals selected 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, C1-C6-haloalkylsulfonyl;
• or
• two radicals R9 which are attached to the same carbon together with this carbon form a carbonyl group;
• or
• two radicals R9 which are attached to different carbons together form a —(CH2)n— chain which may be substituted by one to three radicals selected from the following group:
• halogen, C1-C6-alkyl, C1-C6-alkoxy, hydroxyl or C1-C6-alkoxycarbonyl;
• R10 is C1-C6-alkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkynyl, C3-C6-haloalkynyl, C3-C6-cycloalkyl, C1-C20-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—(C1C6-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, where the abovementioned alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and/or may 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;
• is phenyl, heterocyclyl, phenyl-C1-C6-alkyl, heterocyclyl-C1-C6-alkyl, phenylcarbonyl-C1-C6-alkyl, heterocyclylcarbonyl-C1-C6-alkyl, phenylcarbonyl, heterocyclylcarbonyl, phenoxycarbonyl, phenyloxythiocarbonyl, heterocyclyloxycarbonyl, heterocyclyloxythiocarbonyl, phenylaminocarbonyl, N—(C1-C6-alkyl)-N-(phenyl)aminocarbonyl, heterocyclylaminocarbonyl, N—(C1-C6-alkyl)-N-(heterocyclyl)aminocarbonyl, phenyl-C2-C6-alkenylcarbonyl or heterocyclyl-C2-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;
• R11, R12 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-C6-alkyl)amino or di-(C1-C6-haloalkyl)amino, where the abovementioned alkyl, cycloalkyl and alkoxy radicals may be partially or fully halogenated and/or may 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;
• are phenyl, heterocyclyl, phenyl-C1-C6-alkyl, heterocyclyl-C1-C6-alkyl, phenoxy, heterocyclyloxy, where the phenyl and the heterocyclyl radical of the 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;
• R13 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 selected 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;
• is phenyl, heterocyclyl, phenyl-C1-C6-alkyl or heterocyclyl-C1-C6-alkyl, where the phenyl or heterocyclyl radical of the four 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;
• R14 is C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl or C1-C6-alkylcarbonyl;
• q is 0 to 6
• and agriculturally useful salts thereof.