Tricyclic benzoylcyclohexanedione derivatives

A tricyclic benzoylcyclohexanedione derivative of the formula I

• where:
• X is oxygen, sulfur, S═O, or S(═O)2;
• Y together with the two carbon atoms to which it is attached forms a saturated, partially saturated or unsaturated 5-membered heterocycle which contains one to three identical or different heteroatoms selected from the following group:
• oxygen, sulfur or nitrogen;
• R1, R2 are hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy;
• R3 is halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy;
• R4 is 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, 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;
• R5 is hydrogen, C1-C6-alkyl or halogen;
• m is 0, 1 or 2;
• R9 is a radical IIa or IIb
• where:
• R10 is hydroxyl, mercapto, halogen, OR17, SR17, SOR18, SO2R18, OSO2R18, NR19R20 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;
• R11, R15 are hydrogen, C1-C4-alkyl or C1-C4-alkoxycarbonyl;
• R12, R14, R16 are hydrogen or C1-C4-alkyl;
• R13 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, C3-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 last-mentioned radicals may be substituted by one to three C1-C4-alkyl radicals;
• or
• R12 and R13 or R13 and R16 together form a π-bond or a C1-C5-alkyl chain which may carry one to three radicals from the following group:
• halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxycarbonyl;
• or
• R12 and R16 together form a C1-C4-alkyl chain which may carry one to three radicals from the following group:
• halogen, cyano, C3-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxycarbonyl;
• R13 and R14 together form a —O—(CH2)p—O—, —O—(CH2)p—S—, —S—(CH2)p—S—, —O—(CH2)q— or —S—(CH2)q— chain which may be substituted by one to three radicals from the following group:
• halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxycarbonyl;
• or
• R13 and R14 together with the carbon to which they are attached form a carbonyl group;
• R17 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—(C1-C6-alkoxy)-aminocarbonyl, di-(C1-C6-alkyl)-aminothiocarbonyl, C1-C6-alkoxyimino-C1-C6-alkyl, where the alkyl, cycloalkyl or alkoxy radicals mentioned 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, 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 or the heterocyclyl radical of the 18 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;
• R18 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 to 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 or the heterocyclyl radical of the four 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, C1-C4-haloalkoxy or C1-C4-alkoxycarbonyl;
• R19 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 to three of the following radicals:
• cyano, C1C4-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 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;
• R20 is hydrogen, C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl;
• p is 2, 3 or 4;
• q is 1, 2, 3, 4 or 5;
• and their agriculturally useful salts.