3-(Het)aryloxy(thio)carboxylic acid derivatives, their preparati

Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing

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504239, 504242, 504243, 544216, 544217, 544218, 544219, 544302, 544314, 544318, 544319, 544335, H01N 4354, C07D23960, C07D23952, C07D33324

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056611064

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BRIEF SUMMARY
This application is a 371 of PCT/EP94/01156, filed Apr. 14, 1994.
The present invention relates to 3-(het)aryloxy(thio)carboxylic acid derivatives of the general formula I ##STR2## where R.sup.1 is atom, contains two or three nitrogen atoms and may carry one or two halogen atoms and/or one or two of the following radicals: -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy and/or C.sub.1 -C.sub.4 -alkylthio; ##STR3## where m is 0 or 1 and R.sup.7 and R.sup.8, which may be identical or different, have the following meanings: -alkynyl or C.sub.3 -C.sub.12 -cycloalkyl, where each of these radicals may carry one to five halogen atoms and/or one or two of the following groups: -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.6 -alkylcarbonyl, C.sub.3 -C.sub.6 -alkenylcarbonyl, C.sub.3 -C.sub.6 -alkynylcarbonyl, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.3 -C.sub.6 -alkenyloxycarbonyl, C.sub.3 -C.sub.6 -alkynyloxycarbonyl, di-C.sub.1 -C.sub.4 -alkylamino, cyclo-C.sub.1 -C.sub.6 -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; 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; -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; ##STR4## 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 -akylthio [sic], 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. metal cation, the ammonium cation or an organic ammonium ion; -C.sub.4 -alkyl radicals; and/or one of the following radicals: -C.sub.8 -alkylcarbonyl, C.sub.3 -C.sub.12 -cycloalkyl, C.sub.1 -C.sub.8 -alkoxycarbonyl, phenyl, phenoxy or phenylcarbonyl, where the aromatic radicals in turn may each carry one to five halogen atoms and/or one to three of the following radicals: -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy and/or C.sub.1 -C.sub.4 -alkylthio; 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, each of its structures may carry one to four halogen atoms and/or one or two of the following radicals: -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy and/or C.sub.1 -C.sub.4 -alkylthio; the 2 position: C.sub.1 -C.sub.6 -alkoxyimino, C.sub.3 -C.sub.6 -alkenyloxyimino, C.sub.3 -C.sub.6 -haloalkenyloxyimino or benzyloxyimino; groups in turn may carry one to five halogen atoms; the following radicals: -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy and/or C.sub.1 -C.sub.4 -alkylthio; atom, contains one to three nitrogen atoms and may carry one or two halogen atoms and/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 and/or C.sub.1 -C.sub.4 -alkylthio; ##STR5## where R.sup.11 and R.sup.12 may be identical or different and are each: C.sub.1 -C.sub.10 -alkyl, C.sub.3 -C.sub.6 -alkenyl, C.sub.3 -C.sub.6 -alkynyl or C.sub.3 -C.sub.7 -cycloalkyl, where these radicals may carry one C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkylthio and/or one phenyl radical; -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -alkylthio; which may carry one to three C.sub.1 -C.sub.4 -alkyl groups; ##STR6## 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

REFERENCES:
patent: 5270289 (1993-12-01), Harde et al.
J. March, Advanced Organic Chem. 2nd ed, 1983, p. 862 and 750.
Japanese Abstracts JP 3193765 (1991).
28 Heterocycles, vol. 119, 1993, p. 883.
Direct Enantiomeric . . . , Nishi et al., Chromatographia, vol. 35, No. 5/6, Mar. 1993.
Aust J. Chem, 1992, 45, 1833-1843, Brown et al.
Synthesis and Antihypertensive . . . , Chem. Pharm. Bull. 40(8) 2055-2061 (1992).
Advanced Organic Chemistry, Third Ed., Jerry March p. 862 and 750 (1983).

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