Novel carboxylic acid derivatives, their preparation and use

A carboxylic acid derivative of the formula I

• where R is formyl, tetrazole [sic], nitrile [sic], a COOH group or a radical which can be hydrolyzed to COOH, and the other substituents have the following meanings:
• R2 hydrogen, hydroxyl, NH2, NH(C1-C4-alkyl), N(C1-C4-alkyl)2, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkylthio;
• X 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 a methylene group can be replaced by oxygen, sulfur, —NH or —NC1-4-alkyl;
• R3 hydrogen, hydroxyl, NH2, NH(C1-C4-Alkyl), N(C1-C4-alkyl)2, 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 give a 5- or 6-membered ring;
• R4 and R5 (which can be identical or different):
• phenyl or naphthyl, 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-di-alkylamino;
• or
• phenyl or naphthyl, which are connected together in the ortho positions via a direct linkage, a methylene, ethylene or ethenylene group, an oxygen or sulfur atom or an SO2, NH or N-alkyl group
• or C3-C7-cycloalkyl;
• R6 hydrogen, C1-C8-alkyl, C3-C6-alkenyl, C3-C5-alkynyl or C3-C8-cycloalkyl, where each of these radicals can be substituted one or more times by:
• halogen, nitro, cyano, C1-C4-alkoxy, C3-C6-alkenyloxy, C3-C5-alkynyloxy, C1-C4-alkylthio, C1-C4-haloalkoxy, C1-C4-alkylcarbonyl, C1-C4-alkoxycarbonyl, C3-8-alkylcarbonylalkyl, C1-C4-alkylamino, di-C1-C4-alkylamino, phenyl or phenyl or phenoxy which is substituted one or more times, eg. one to three times, by halogen, nitro, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy or C1-C4-alkylthio;
• phenyl or naphthyl, each of which can be substituted by one or more of the following radicals:
• halogen, nitro, cyano, hydroxyl, amino, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, phenoxy, C1-C4-alkylthio, C1-C4-alkylamino, C1-C4-dialkylamino or dioxomethylene [sic] or dioxoethylene [sic];
• a five- or six-membered heteroaromatic moiety containing one to three nitrogen atoms and/or one sulfur or oxygen atom, which can carry one to four halogen atoms and/or one or two of the following radicals:
• C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, phenyl, phenoxy or phenylcarbonyl, it being possible for the phenyl radicals in turn to carry one to five halogen atoms and/or one to three of the following radicals:
• C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy and/or C1-C4-alkylthio;
• with the proviso that R6 can be hydrogen only when Z is not a single bond;
• Y sulfur or oxygen or a single bond;
• Z sulfur, oxygen, —SO—, —SO2— or a single bond.