Carboxylic acid derivatives, their production and use

A compound of formula I

• where R is a group —(CO)—R1
• where R1 is:
• a) a radical
• where m is 0 or 1 and R7 and R8, which can be identical or different, have the following meanings:
• hydrogen, C1-C8-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C3-C8-cycloalkyl, it being possible for these alkyl, cycloalkyl, alkenyl and alkynyl groups each to carry one to five halogen atoms, and/or one or two of the following groups:
• C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-haloalkoxy, C3-C6-alkenyloxy, C3-C6-alkenlthio, C3-C6-alkynyloxy, C3-C6-alkynylthio, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, C3-C6-alkenylcarbonyl, C3-C6-alkynylcarbonyl, C3-C6-alkenyloxycarbonyl and C3-C6-alkynyloxycarbonyl, phenyl, unsubstituted or substituted one or more times, by halogen, nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkylthio, di-C1-C4-alkylamino,
• R7 and R8 are furthermore phenyl which is unsubstituted or substituted by one or more of the following radicals:
• halogen, nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkylthio, or R7 and R8 together form a C4-C7-alkylene chain which is closed to form a ring and may contain a hetero atom selected from the group of oxygen, sulfur or nitrogen;
• b) a group
• in which k assumes the values 0, 1 and 2, p assumes the values 1, 2, 3 and 4, and
• R9 is C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-alkenyl, C3-C6-alkynyl or phenyl which is unsubstituted or substituted by one or more of the following radicals:
• halogen, nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkylthio;
• c) a radical —OR10 where R10 is:
• hydrogen, an ammonium ion, the cation of an alkali metal, the cation of an alkaline earth metal or a tertiary C1-C4-alkyl ammonium;
• C3-C8-cycloalkyl, which can carry one to three C1-C4-alkyl groups;
• C1-C8-alkyl which can carry one to five halogen atoms and/or one of the following radicals:
• C1-C4-alkoxy, C1-C4-alkylthio, cyano, C1-C4-alkylcarbonyl, C3-C8-cycloalkyl, C1-C4-alkoxycarbonyl, phenyl, phenoxy or phenylcarbonyl, it being possible for the aromatic radicals in turn each to carry one to five halogen atoms and/or one to three of the following radicals:
• nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and/or C1-C4-alkylthio;
• a C1-C8-alkyl group which can carry one to five halogen atoms and carries a 5-membered heteroaromatic system consisting of one to three nitrogen atoms and two to four carbon atoms, or a 5-membered heteroaromatic system consisting of one nitrogen atom, one oxygen or sulfur atom, and three carbon atoms wherein said 5-membered heteroaromatic system consisting of one to three nitrogen atoms and two to four carbon atoms can carry one to four halogen atoms and/or one or two of the following radicals:
• nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, phenyl, C1-C4-haloalkoxy and/or C1-C4-alkylthio;
• a C2-C6-alkyl group which carries in position 2 one of the following radicals:
• C1-C4-alkoxyimino, C3-C6-alkynyloxyimino, C3-C6-haloalkenyloxyimino or benzyloxyimino;
• a C3-C6-alkenyl or a C3-C6-alkynyl group, it being possible for these groups in turn to carry one to five halogen atoms;
• R10 is furthermore a phenyl radical which can carry one to five halogen atoms and/or one to three of the following radicals:
• nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and/or C1-C4-alkylthio;
• a 5-membered heteroaromatic system which is linked via a nitrogen atom and consists of one to three nitrogen atoms and which can carry one or two halogen atoms and/or one or two of the following radicals:
• C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, phenyl, C1-C4-haloalkoxy or C1-C4-alkylthio;
• R10 is furthermore a group
• where R11 and R12, which can be identical or different, are:
• C1-C8-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C3-C8-cycloalkyl, it being possible for these radicals to carry a C1-C4-alkoxy, C1-C4-alkylthio and/or a phenyl radical which is unsubstituted or substituted by one or more of the following radicals:
• halogen, nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkylthio;
• phenyl which is unsubstituted or substituted by one or more of the following radicals:
• halogen, nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkylthio, or R11 and R12 together form a C3-C12-alkylene chain which may carry one to three C1-C4-alkyl groups and optionally contains a hetero atom from the group of oxygen, sulfur and nitrogen;
• d) a radical
• where R13 is:
• C1-C4-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C3-C8-cycloalkyl, it being possible for these radicals to carry a C1-C4-alkoxy-, C1-C4-alkylthio- and/or phenyl radical;
• phenyl which is unsubstituted or substituted by one or more of the following:
• halogen, nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkylthio;
• or
• e) a radical
• where R13 has the abovementioned meaning;
• R2 is halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkylthio;
• X is nitrogen or CR14, where R14 is hydrogen or C1-5-alkyl, or CR14 forms together with CR3 a 5- or 6-membered alkylene or alkenylene ring which can be substituted by one or two C1-4-alkyl groups and in which in each case one methylene group can be replaced by oxygen, sulfur, —NH or —NC1-4-alkyl;
• R3 is halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, —NH—O—C1-4-alkyl, C1-C4-alkylthio or CR3 is linked to CR14 as indicated above to form a 5- or 6-membered ring;
• R4 and R5, which may be identical or different, are:
• phenyl or naphthyl, each of which can be substituted by one or more of the following radicals:
• halogen, nitro, cyano, hydroxyl, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, phenoxy, C1-C4-alkylthio, amino, C1-C4-alkylamino or C1-C4-dialkylamino;
• or phenyl or naphthyl which are connected together in ortho positions by a direct linkage, a methylene, ethylene or ethenylene group, an oxygen or sulfur atom or SO2, NH or N-alkyl group, or C3-C7-cyloalkyl;
• R6 is C1-C10-alkyl, C3-C10-alkenyl or C3-C10-alkynyl, the radicals each being substituted one or more times by hydroxyl, mercapto, carboxyl, sulfonyl, guanidino, or
• where Ry and Rz are, independently of one another, hydrogen or C1-C5-alkyl;
• and
• Z is sulfur or oxygen.