Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1995-10-19
1997-08-26
Raymond, Richard L.
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
504239, 504242, 504243, 544216, 544217, 544218, 544219, 544302, 544314, 544318, 544319, 544335, H01N 4354, C07D23960, C07D23952, C07D33324
Patent
active
056611064
DESCRIPTION:
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
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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).
Baumann Ernst
Bratz Matthias
Gerber Matthias
Meyer Norbert
Rademacher Wilhelm
BASF - Aktiengesellschaft
Raymond Richard L.
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