3-Arylisothiazoles and their use as herbicides

A 3-arylisothiazole of the formula I

• 78
• in which the variables X, Q, R1, R2, R3, R4, R5 are as defined below:
• X is a chemical bond, a methylene, 1,2-ethylene, propane-1,3-diyl, ethene-1,2-diyl or ethyne-1,2-diyl chain or an oxymethylene or thiamethylene chain which is attached to the phenyl ring via the heteroatom, where all chains may be unsubstituted or may carry one or two substituents, in each case selected from the group consisting of cyano, carboxyl, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, (C1-C4-alkoxy)carbonyl, di(C1-C4-alkyl)amino and phenyl;
• R1 is C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkylsulfinyl, C1-C4-haloalkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl, C1-C4-alkylsulfonyloxy or C1-C4-haloalkylsulfonyloxy;
• R2 is hydrogen, halogen, amino, cyano, nitro, C1-C4-alkyl or C1-C4-haloalkyl;
• R3 is hydrogen or halogen;
• R4 is hydrogen, cyano, nitro, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy or C1-C4-haloalkoxy;
• R5 is hydrogen, nitro, cyano, halogen, halosulfonyl, —O—Y—R7, —O—CO—Y—R7, —N(Y—R7)(Z—R8), —N(Y—R7)—SO2—Z—R8, —N(SO2—Y—R7)(SO2—Z—R8), —N(Y—R7)—CO—Z—R8, —N(Y—R7)(O—Z—R8), —S—Y—R7, —SO—Z—R7, —SO2—Y—R7, —SO2—O—Y—R7, —SO2—N(Y—R7)(Z—R8), —CO—Y—R7, —C(═NOR9)—Y—R7, C(═NOR9)—O—Y—R7, —CO—O—Y—R7, —CO—S—Y—R7, —CO—N(Y—R7)(Z—R8), —CO—N(Y—R7)(O—Z—R8) or —PO(O—Y—R7)2;
• Q is nitrogen or a group C—R6 in which R6 is hydrogen;
• or
• R4 and X—R5 or X—R5 and R6 are a 3- or 4-membered chain whose chain members may, in addition to carbon, include 1, 2 or 3 heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur and which may be unsubstituted or may for its part carry one, two or three substituents, and whose members may also include one or two not adjacent carbonyl, thiocarbonyl or sulfonyl groups,
• where at least one of the variables R3, R4 and/or the group X—R5 is different from hydrogen and where the variables Y, Z, R7, R8 and R9 are as defined below:
• Y, Z independently of one another are:
• a chemical bond, a methylene or ethylene group which may be unsubstituted or may carry one or two substituents, in each case selected from the group consisting of carboxyl, C1-C4-alkyl, C1-C4-haloalkyl, (C1-C4-alkoxy)carbonyl and phenyl;
• R7, R8 independently of one another are:
• hydrogen, C1-C6-haloalkyl, C1-C4-alkoxy-C1-C4-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, —CH(R10)(R11), —C(R10)(R11)—NO2, —C(R10)(R11)—CN, —C(R10)(R11)-halogen, —C(R10)(R11)—OR12, —C(R10)(R11)—N(R12)R13, —C(R10)(R11)—N(R12)—OR13, —C(R10)(R11)—SR12, —C(R10)(R11)—SO—R12, —C(R10)(R11)—SO2—R12, —C(R10)(R11)—SO2—OR12, —C(R10)(R11)—SO2—N(R12)R13, —C(R10)(R11)—CO—R12, —C(R10)(R11)—C(═NOR14)—R12, —C(R10)(R11)—CO—OR12, —C(R10)(R11)—CO—SR12, —C(R10)(R11)—CO—N(R12)R13, —C(R10)(R11)—CO—N(R12)—OR13, —C(R10)(R11)—PO(OR12)2, C3-C8-cycloalkyl which may contain a carbonyl or thiocarbonyl ring member, phenyl or 3-, 4-, 5-, 6- or 7-membered heterocyclyl which may contain a carbonyl or thiocarbonyl ring member, where each cycloalkyl, the phenyl and each heterocyclyl ring may be unsubstituted or may carry one, two, three or four substituents, in each case selected from the group consisting of cyano, nitro, amino, hydroxyl, carboxyl, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl, (C1-C4-alkyl)carbonyl, (C1-C4-haloalkyl)carbonyl, (C1-C4-alkyl)carbonyloxy, (C1-C4-haloalkyl)carbonyloxy, (C1-C4-alkoxy)carbonyl and di(C1-C4-alkyl)amino;
• R9 is hydrogen, C1-C6-alkyl, C1-C4-alkoxycarbonyl-C1-C4-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, phenyl or phenyl-C1-C4-alkyl;
• where the variables R10 to R14 are as defined below:
• R10, R11 independently of one another are hydrogen, C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl, (C1-C4-alkoxy)carbonyl-C1-C4-alkyl or phenyl-C1-C4-alkyl, where the phenyl ring may be unsubstituted or may carry one to three substituents, in each case selected from the group consisting of cyano, nitro, carboxyl, halogen, C1-C4-alkyl, C1-C4-haloalkyl and (C1-C4-alkoxy)carbonyl;
• R12, R13 independently of one another are hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C4-alkoxy-C1-C4-alkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, C3-C8-cycloalkyl-C1-C4-alkyl, phenyl, phenyl-C1-C4-alkyl, 3- to 7-membered heterocyclyl or heterocyclyl-C1-C4-alkyl, where each cycloalkyl and each heterocyclyl ring may contain a carbonyl or thiocarbonyl ring member, and where each cycloalkyl, the phenyl and each heterocyclyl ring may be unsubstituted or may carry one, two, three or four substituents, in each case selected from the group consisting of cyano, nitro, amino, hydroxyl, carboxyl, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl, (C1-C4-alkyl)carbonyl, (C1-C4-haloalkyl)carbonyl, (C1-C4-alkyl)carbonyloxy, (C1-C4-haloalkyl)carbonyloxy, (C1-C4-alkoxy)carbonyl and di(C1-C4-alkyl)amino;
• R14 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C8-cycloalkyl, phenyl or phenyl-C1-C4-alkyl;
• and the agriculturally useful salts of I.