Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1995-10-19
1997-12-30
Clardy, S. Mark
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
504228, 504230, 504239, 504240, 504241, 504242, 504243, 544219, 544235, 544242, 544253, 544319, 546340, 546341, 548204, 548248, 5483415, 5483761, 549 79, 549498, 549499, 562426, 562470, 568 41, 568425, 568496, A01N 4354, A01N 4366, C07D23960, C07D25130, C07D40912, C07D40112, C07D40512, C07C 69734
Patent
active
057030170
DESCRIPTION:
BRIEF SUMMARY
This application has been filed under 35 USC 371 as a national stage application of PCT/EP94/01141, filed Apr. 13, 1994.
BACKGROUND OF THE INVENTION
3-(het)arylcarboxylic acid derivatives of the general formula I ##STR2## where R is formyl, CO.sub.2 H or a radical hydrolyzable to COOH, and the other substituents have the following meanings: C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -alkylthio; 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; 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; 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; 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; -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; when R.sup.4 is unsubstituted phenyl, Z is oxygen and simultaneously R.sup.5 is methyl or hydrogen.
The prior art, eg. EP-A 347 811, EP-A 400 741, EP-A 409 368, EP-A 481 512, EP-A 517 215, Chemical Abstracts, 119, No. 139 254e (1993), and the prior German application P 41 42 570 (EP-A-548 710), describes similar carboxylic acid derivatives, including 3-alkoxy derivatives but not those which carry a het(aryl) radical in the 3 position.
SUMMARY OF THE INVENTION
Since the herbicidal and/or bioregulatory action and selectivity of the known compounds is not always satisfactory, it is an object of the present invention to provide compounds having better selectivity and/or better biological activity.
We have found that this object is achieved and that the 3-(het)arylcarboxylic acid derivatives defined at the outset have excellent herbicidal and plant growth-regulating properties. Furthermore, the compounds I have good pharmacological efficacy, particularly in the cardiovascular sector.
The preparation of the novel compounds starts from the epoxides IV, which are obtained in a generally known manner, as described, for example, in J. March, Advanced Organic Chemistry, 2nd ed., 1983, page 862 and page 750, from the aldehydes or ketones II or the olefins III: ##STR3##
3-(Het)arylcarboxylic acid derivatives of the general formula VI can be prepared by reacting the epoxide of the general formula IV (for example, with R=ROOR.sup.10) with alcohols or thiols of the general formula V, where R.sup.6 and Z have the meanings stated in claim 1. ##STR4##
For this purpose, compounds of t
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patent: 5270289 (1993-12-01), Harde et al.
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Chemical Abstracts vol. 119, 1993, No. 13, Ab 119:139254e.
Chemical Abstracts, vol. 85, No. 5, Aug. 2, 1976, Ab:85:32649a.
Agr. Biol. Chem. 40(5),933-1000,1976, On the Sterochemistry . . . Kogure et al.
Advanced Organic Chem., Third Ed., Jerry March 1985, pp. 750, 863.
Bul.Chem Soc. of Japan, vol. 49(1), 341-342,1976, Photochemical Reaction . . . Chung et al.
Baumann Ernst
Bratz Matthias
Gerber Matthias
Rademacher Wilhelm
Rheinheimer Joachim
BASF - Aktiengesellschaft
Clardy S. Mark
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