Benzoyl derivatives, process for their preparation and their use as herbicides and plant growth regulators

A compound of the formula (I)

• in which
• Q is a radical of the formula (II), (III) or (IV)
• R1, R2, R3 independently of one another are hydrogen, hydroxyl, thio, amino, cyano, nitro, halogen or an unsubstituted or substituted hydrocarbon radical which may or may not contain one or more additional, identical or different, heteroatoms selected from the group consisting of oxygen, sulfur, nitrogen, fluorine, chlorine, bromine and iodine;
• R4 is hydrogen, cyano, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxylcarbonyl, phenyl, where the six last-mentioned groups are unsubstituted or substituted by one or more identical or different radicals selected from the group consisting of halogen, nitro, cyano, alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy and alkylthio;
• R5 is heteroaryl, heterocyclyl or aryl which is unsubstituted or mono- or polysubstituted by identical or different radicals, or is a radical selected from the group consisting of —O—N═CRlRm, —P(═O)(ORi)(Rj), —P(═O)(ORj)(ORk) or
• or, if E is a bond and l is zero and Q is other than a radical formula II where G1-G2 is NR0COR″, then R5 is also hydroxyl,
• A is a divalent unit selected from the group consisting of O, S, SO, and SO2;
• B is a chain which has two carbon atoms, which is saturated or contains one or more multiple bonds and which is unsubstituted or substituted by alkyl, haloalkyl, alkoxy, haloalkoxy or by an unsubstituted or alkyl-, haloalkyl-, alkoxy-, haloalkoxy-, halogen-, cyano- or nitro-substituted phenyl radical;
• E is a bond, a one- to six-membered chain which is saturated or contains one or more multiple bonds and which consists of divalent units selected from the group consisting of C, CRc, CRcRd, N, NRc, S, SO, SO2, O and CO;
• X is a divalent unit selected from the group consisting of O, S and NRe;
• R6 is alklylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, cyano, cyanato, thiocyanato, halogen or ORf;
• Y is a divalent unit selected from the group consisting of O, S, NH, N-alkyl or CHR7;
• R7 is hydrogen, tetrahydropyran-3-yl, tetrahydropyran-4-yl, tetrahydrothiopyran-3-yl, alkyl, cycloalkyl, alkoxy, alkoxyalkyl, alkylcarbonyl, alkoxycarbonyl, alkylthio, phenyl, where the hydrocarbon moiety of the eight last-mentioned radicals is unsubstituted or substituted by one or more identical or different radicals selected from the group consisting of halogen, alkylthio and alkyloxy, or
• two radicals R7 which are attached to a joint carbon atom form a chain selected from the group consisting of OCH2CH2O, OCH2CH2CH2O, SCH2CH2S and SCH2CH2CH2S, this chain being unsubstiuted or substituted by one to four methyl groups, or
• two radicals R7 which are attached to directly adjacent carbon atoms form a bond or together with the carbon atoms that carry them form an unsubstituted or substituted 3- to 6-membered ring;
• Z is a bond, a divalent unit selected from the group consisting of O, S, SO, SO2, NH, N-alkyl or CHR7, where Y and Z shoul not simultaneously be a divalent unit which contains an oxygen, nitrogen or sulfur atom as chain member;
• G1-G2 is a divalent unit selected from the group consisting of OCR9, SCR9 and NR10COR11, where the attachment to the ring system is to be carried out such that the carbon atom of this divalent unit is in each case attached to the carbon atom of the ring system via a double bond;
• R8 is hydrogen, alkyl or alkoxycarbonyl;
• R9 is hydrogen, alkyl, cycloalkyl, haloalkyl or halocycloalkyl;
• R10 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, benzyl, where the six last-mentioned groups are unsubstituted or substituted by one or more identical or different radicals selected from the group consisting of halogen, cyano, nitro and alkoxy;
• R11 is hydrogen, formyl, alkyl, haloalkyl, alkoxyalkyl or a group L-R12;
• L is a divalent unit selected from the group consisting of SO2, CO, CHRgCO or CRgRh;
• R12 is alkyl, haloalkyl, alkoxy, haloalkoxy, alkylamino, dialkylamino, cycloalkyl or is phenyl which is unsubstituted or substituted by one or more identical or different radicals selected from the group consisting of cyano, nitro, alkyl, alkoxy, haloalkyl and haloalkoxy;
• Rc and Rd independently of one another are hydrogen, halogen, nitro, cyano, alkyl, haloalkyl, cycloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, haloalkylcarbonylamino, alkylcarbonyl-N-alkylamino, alkylsulfonyl, alkylsulfinyl, alkylsulfonylamino, haloalkylsulfonyl, haloalkylsulfinyl, alkylsulfonylamino and alkylsulfonyl-N-alkylamino;
• Re is hydrogen, formyl, alkyl, cycloalkyl, alkenyl, alkynyl, alkylcarbonyl and alkylsulfonyl, where the hydrocarbon moiety of the six last-mentioned radicals may be unsubstituted or substituted by one or more identical or different radicals selected from the group consisting of halogen, nitro, cyano, alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy and alkylthio;
• Rf is hydrogen, alkyl, haloalkyl, alkoxyalkyl, formyl, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylsulfonyl, haloalkylsulfonyl, benzoyl or phenylsulfonyl, where the aromatic moiety of the two last-mentioned radicals is unsubstituted or substituted by one or more identical or different radicals selected from the group consisting of alkyl, haloalkyl, alkoxy, haloalkoxy, halogen, cyano and nitro;
• Rg and Rh independently of one another are hydrogen or alkyl;
• Ri and Rk independently of one another are hydrogen or Rj;
• Rj is alkyl, alkenyl, haloalkyl, haloalkenyl, phenyl, benzyl, where these six abovementioned radicals are unsubstittded or substituted by one or more identical or different radicals selected from the group consisting of halogen, cyano, nitro, (C1-C4)-alkyl, (C1-C4)-alkoxy, halogen-(C1-C4)-alkyl or halo-(C1-C4)-alkoxy;
• Rl and Rm independently of one another are hydrogen or alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl or haloalkynyl which is substituted by one or more identical or different radicals R1, or
• Rl and Rm together with the carbon atom to which they are attached form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated ring which may or may not contain one to three heteroatoms selected from the group consisting of oxygen, sulfur and nitrogen and which is unsubstituted or substituted by one or more identical or different radicals R1;
• R10 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, phenyl, benzyl, where the six last-mentioned groups are unsubstituted or substituted by one or more identical or different radicals selected from the group consisting of halogen, cyano, nitro and alkoxy;
• R11 is hydrogen, formyl, alkyl, haloalkyl, alkoxyalkyl or a group L-R12;
• L is a divalent unit selected from the group consisting of SO2, CO, CHRgCO or CRgRh;
• R12 is alkyl, haloalkyl, alkoxy, haloalkoxy, alkylamino, dialkylamino, cycloalkyl or is phenyl which is unsubstituted or substituted by one or more identical or different radicals selected from the group consisting of cyano, nitro, alkyl, alkoxy, haloalkyl and haloalkoxy;
• Rc and Rd independently of one another are hydrogen, halogen, nitro, cyano, alkyl, haloalkyl, cycloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylcardonyl, haloalkylcarbonyl, alkoxycarbonyl, haloalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, haloalkylcarbonylamino, alkylcarbonyl-N-alkylamino, alkylsulfonyl, alkylsulfinyl, alkylsulfonylamino, haloalkylsulfonyl, haloalkylsulfinyl, alkylsulfonylamino and alkylsulfonyl-N-alkylamino;
• l is 0 or 1;
• m is 0, 1 or 2;
• n is 0, 1, 2 or 3;
• v is 1 or 2;
• w is 0, 1, 2, 3 or 4,
• with the proviso that
• d) the compound 4-[2-tetrahydrofuryl]methyloxy-5,8-dimethyl-6-[(2,6-dioxocyclohexyl)carbonyl]-1,2,3,4-tetrahydro-1λ6-thiochromene-1,1-dione is not embraced by the above definition and
• e) in R5 aryl is not phenyl if E is methylene and G1 in G1-G2 is sulfur.