Claims for Patent: 5,703,017

Summary for Patent: 5,703,017

Title:	3-(Het) arylcarboxylic acid derivatives, their preparation and intermediates for their preparation
Abstract:	3-(Het)arylcarboxylic acid derivatives of the formula I ##STR1## where R is formyl, CO.sub.2 H or a radical hydrolyzable to COOH and the other substituents have the following meanings: R.sup.2 and R.sup.3 are each halogen, alkyl, haloalkyl, alkoxy, haloalkoxy or alkylthio; X is nitrogen or CR.sup.14, where R.sup.14 is hydrogen or, together with R.sup.3, forms an alkylene or alkenylene chain, in each of which a methylene group is replaced by oxygen; R.sup.4 is phenyl or naphthyl, each of which is unsubstituted or substituted or an unsubstituted or substituted five-membered or six-membered heteroaromatic structure containing one to three nitrogen atoms or one sulfur or oxygen atom; R.sup.5 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, haloalkyl, alkoxyalkyl, alkylthioalkyl or phenyl; R.sup.6 is C.sub.1 -C.sub.8 -alkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl or C.sub.3 -C.sub.4 -cyclo-alkyl, each of which may be mono- or polysubstituted; Y is sulfur, oxygen or a single bond; and Z is sulfur or oxygen; with the proviso that R.sup.6 is not unsubstituted C.sub.1 -C.sub.4 -alkyl when R.sup.4 is unsubstituted phenyl, Z is oxygen and simultaneously R.sup.5 is methyl or hydrogen.
Inventor(s):	Baumann; Ernst (Dudenhofen, DE), Rheinheimer; Joachim (Ludwigshafen, DE), Vogelbacher; Uwe Josef (Ludwigshafen, DE), Bratz; Matthias (Speyer, DE), Theobald; Hans (Limburgerhof, DE), Gerber; Matthias (Limburgerhof, DE), Westphalen; Karl-Otto (Speyer, DE), Walter; Helmut (Obrigheim, DE), Rademacher; Wilhelm (Limburgerhof, DE)
Assignee:	BASF Aktiengesellschaft (Ludwigshafen, DE)
Application Number:	08/537,843
Patent Claims:	1. A 3-(het)arylcarboxylic acid derivative of the formula I ##STR15## where R is formyl, CO.sub.2 H or a radical hydrolyzable to COOH and R.sub.2 is halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -alkylthio; X is nitrogen or CR.sup.14, where R.sup.14 is hydrogen or, together with R.sup.3, forms a 3-membered or 4-membered alkylene or alkenylene chain, in each of which a methylene group is replaced by oxygen; R.sup.3 is halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -alkylthio or R.sup.3 is linked to R.sup.14 as stated above to form a 5-membered or 6-membered ring; R.sup.4 is phenyl or naphthyl which may be substituted by one or more, in particular one to three, of the following radicals: halogen, nitro, cyano, hydroxyl, mercapto, amino, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkylamino, di-C.sub.1 -C.sub.4 -alkylamino, C.sub.1 -C.sub.4 -alkylcarbonyl or C.sub.1 -C.sub.4 -alkoxycarbonyl; a five-membered or six-membered heteroaromatic structure which contains one to three nitrogen atoms and/or one sulfur or oxygen atom and may carry one or more of the following radicals: halogen, nitro, cyano, hydroxyl, mercapto, amino, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkylamino, C.sub.1 -C.sub.4 -dialkylamino, C.sub.1 -C.sub.4 -alkylcarbonyl, C.sub.1 -C.sub.4 -alkoxycarbonyl or phenyl; R.sup.5 is hydrogen, C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxyalkyl, C.sub.1 -C.sub.4 -alkylthioalkyl or phenyl; R.sup.6 is C.sub.1 -C.sub.8 -alkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl or C.sub.3 -C.sub.8 -cycloalkyl, it being possible for these radicals to be mono- or polysubstituted in each case by: halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkoxy, C.sub.3 -C.sub.6 -alkenyloxy, C.sub.3 -C.sub.6 -alkynyloxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylcarbonyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.1 -C.sub.4 -alkylamino, di-C.sub.1 -C.sub.4 -alkylamino, phenyl or phenyl or phenoxy which is mono- or polysubstituted, for example mono- to trisubstituted, by halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -alkylthio; Y is sulfur or oxygen or a single bond; and Z is sulfur or oxygen; with the proviso that R.sup.6 is not unsubstituted C.sub.1 -C.sub.4 -alkyl when R.sup.4 is unsubstituted phenyl, Z is oxygen and simultaneously R.sup.5 is methyl or hydrogen. 2. A 3-(het)arylcarboxylic acid derivative of the general formula I as claimed in claim 1, where R is ##STR16## where R.sup.1 has the following meanings: a) hydrogen; b) a succinylimidoxy group; c) a 5-membered heteroaromatic structure which is bonded via a nitrogen atom, contains two or three nitrogen atoms and may carry one or two halogen atoms or one or two of the following radicals: C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -alkylthio; d) a radical ##STR17## where m is 0 or 1 and R.sup.7 and R.sup.8, which may be identical or different, have the following meanings: hydrogen; C.sub.1 -C.sub.8 -alkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl or C.sub.3 -C.sub.8 -cycloalkyl, where each of these radicals may carry one to five halogen atoms or one or two of the following groups: C.sub.1 -C.sub.4 -alkoxy, C.sub.3 -C.sub.6 -alkenyloxy, C.sub.3 -C.sub.6 -alkynyloxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.3 -C.sub.6 -alkenylthio, C.sub.3 -C.sub.6 -alkynylthio, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylcarbonyl, C.sub.3 -C.sub.6 -alkenylcarbonyl, C.sub.3 -C.sub.6 -alkynylcarbonyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, C.sub.3 -C.sub.6 -alkenyloxycarbonyl, C.sub.3 -C.sub.6 -alkynyloxycarbonyl, di-C.sub.1 -C.sub.4 -alkylamino, C.sub.3 -C.sub.8 -cycloalkyl, phenyl or phenyl which is monosubstituted or polysubstituted by halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy or c.sub.1 --C.sub.4 -alkylthio; phenyl which may be substituted by one or more of the following radicals: halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -alkylthio; R.sup.7 and R.sup.8 together form a cyclic, optionally substituted C.sub.4 -C.sub.7 -alkylene chain or together form a cyclic, optionally substituted C.sub.3 -C.sub.6 -alkylene chain containing a heteroatom selected from the group consisting of oxygen, sulfur and nitrogen; e) R.sup.1 is furthermore a group ##STR18## where R.sup.9 is C.sub.1 -C.sub.4 -alkyl, phenyl or phenyl which is monosubstituted or polysubstituted by halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -alkylthio, or C.sub.1 -C.sub.4 -haloalkyl, C.sub.3 -C.sub.6 -alkenyl or C.sub.3 -C.sub.6 -alkynyl, p may be 1, 2, 3 or 4 and k may be 0, 1 or 2; f) a radical OR.sup.10, where R.sup.10 is: i) hydrogen, an alkali metal cation, one equivalent of an alkaline earth metal cation, the ammonium cation or an organic ammonium ion; ii) C.sub.3 -C.sub.8 -cycloalkyl Which may carry one to three C.sub.1 -C.sub.4 -alkyl radicals; iii)C.sub.1 -C.sub.8 -alkyl which may carry one to five halogen atoms or one of the following radicals: C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, cyano, C.sub.1 -C.sub.4 -alkylcarbonyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, phenyl, phenoxy or phenylcarbonyl, where the aromatic radicals in turn may each carry one to five halogen atoms or one to three of the following radicals: nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -alkylthio; iv) C.sub.1 -C.sub.8 -alkyl which may carry one to five halogen atoms and carries one of the following radicals: a 5-membered heteroaromatic structure containing one to three nitrogen atoms or a 5-membered heteroaromatic structure containing one nitrogen atom and one oxygen or sulfur atom, which may carry one to four halogen atoms or one or two of the following radicals: nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -alkylthio; v) C.sub.2 -C.sub.6 -alkyl which carries one of the following radicals in the 2 position: C.sub.1 -C.sub.4 -alkoxyimino, C.sub.3 -C.sub.6 -alkenyloxyimino, C.sub.3 -C.sub.6 -haloalkenyloxyimino or benzyloxyimino; vi) C.sub.3 -C.sub.6 -alkenyl or C.sub.3 -C.sub.6 -alkynyl, where these groups in turn may carry one to five halogen atoms; vii)phenyl which may carry one to five halogen atoms or one to three of the following radicals: nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -alkylthio; viii) a 5-membered heteroaromatic structure which has bonded via a nitrogen atom, contains one to three nitrogen atoms and may carry one or two halogen atoms or one or two of the following radicals: nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -alkylthio; ix) R.sup.10 is furthermore a group ##STR19## where R.sup.11 and R.sup.12 , may be identical or different and are each: C.sub.1 -C.sub.8 -alkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl or C.sub.3 -C.sub.8 -cycloalkyl, where these radicals may carry one C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkylthio or one phenyl radical; phenyl which may be substituted by one or more of the following radicals: halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -alkylthio; or R.sup.11 and R.sup.12 together form a C.sub.3 -C.sub.12 -alkylene chain which may carry one to three C.sub.1 -C.sub.4 -alkyl groups; g) or R.sup.1 forms a radical ##STR20## where R.sup.13 is: C.sub.1 -C.sub.4 -alkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl or C.sub.3 -C.sub.8 -cycloalkyl, where these radicals may carry one C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkylthio or one phenyl radical; phenyl which may be substituted by one to five halogen atoms or one to three of the following radicals: nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -alkylthio. 3. A 3-arylcarboxylic acid derivative of the formula I as claimed in claim 1, in which R.sup.4 is phenyl which may be substituted as stated in claim 1, and the remaining substituents have the meanings stated in claim 1. 4. A 3-arylcarboxylic acid derivative of the formula I as claimed in claim 1, in which Z is oxygen, R.sup.4 is phenyl which may be substituted as stated in claim 1, R.sup.5 is methyl, X is CH, R.sup.2 and R.sup.3 are each methoxy and Y, R.sup.1 and R.sup.6 have the meanings stated in claim 1. 5. A 3-hetarylcarboxylic acid derivative of the formula I as claimed in claim 1, in which R.sup.4 is a five- or six-membered heteroaromatic structure as claimed in claim 1 and the remaining substituents have the meanings stated in claim 1. 6. A 3-hetarylcarboxylic acid derivative of the formula I as claimed in claim 1, in which Z is oxygen, R.sup.4 is a five- or six-membered heteroaromatic structure as claimed in claim 1, R.sup.5 is methyl, X is CH, R.sup.2 and R.sup.3 are methoxy and Y, R.sup.1 and R.sup.6 have the meanings stated in claim 1. 7. A herbicide containing a compound of the formula I as claimed in claim 1 and conventional inert additives. 8. A method for controlling undesirable plant growth, wherein a herbicidal amount of a compound of the formula I as claimed in claim 1 is allowed to act on the plants or on their habitat. 9. An agent for influencing plant growth, containing a compound of the formula I as claimed in claim 1 and conventional inert additives. 10. A method for regulating plant growth, wherein a bioregulatory amount of a compound of the formula I as claimed in claim 1 is allowed to act on the plants or on their habitat. 11. A 3-(het)arylcarboxylic acid derivative of the formula VI ##STR21## where R, R.sup.4, R.sup.5, R.sup.6 and Z have the meanings stated in claim 1, with the proviso that R.sup.6 is not unsubstituted alkyl when R.sup.4 is unsubstituted phenyl or 4-isobutylphenyl, Z is oxygen and R.sup.5 is simultaneously methyl or hydrogen. 12. A process for the preparation of a 3-(het)arylcarboxylic acid derivative of the formula VI ##STR22## wherein an epoxide of the formula IV ##STR23## where R, R.sup.4 and R.sup.5 have the meanings stated in claim 1, is reacted with a compound of the formula V where R.sup.6 and Z have the meanings stated in claim 1, with the proviso that R.sup.6 is not unsubstituted alkyl when R.sup.4 is unsubstituted phenyl or 4-isobutylphenyl, Z is oxygen and R.sup.5 is simultaneously methyl or hydrogen, if required in an inert solvent or with the addition of a suitable catalyst. 13. A process for the preparation of 3-(het)arylcarboxylic acid derivatives of the formula I as claimed in claim 1, where is oxygen wherein the 3-het(aryl)carboxylic acid derivative of the formula VI ##STR24## where the substituents have the meanings stated in claim 1, is reacted with a pyrimidyl or triazinyl derivative of the formula VII ##STR25## where R.sup.15 is halogen or R.sup.16 SO.sub.2 -- and R.sup.16 is C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl or phenyl, in an inert solvent in the presence of a base. 14. A process for the preparation of a 3-het(aryl)carboxylic acid derivative of the formula I as claimed in claim 1, where Y is sulfur, wherein a 3-het(aryl)carboxylic acid derivative of the formula VIII ##STR26## where the substituents have the meanings stated in claim 12, is reacted with a pyrimidyl--or triazinylthiol of the formula IX ##STR27## where R.sup.2, R.sup.3 and X have the meanings stated in claim 1, with the proviso that R.sup.6 is not unsubstituted alkyl when R.sup.4 is unsubstituted phenyl or 4-isobutylphenyl, Z is oxygen and R.sup.5 is simultaneously methyl or hydrogen.