Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Ester doai
Patent
1996-11-01
2000-08-22
Shippen, Michael L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Ester doai
514461, 514464, 549447, 549500, 560124, A01N 5300
Patent
active
061073393
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to novel derivatives of esters of carboxylic acids, processes for manufacturing the same, and insecticides and insect proofing agents containing the same.
BACKGROUND ART
Compounds of a natural and a synthetic pyrethroid series are widely used in the fields of agricultural use as well as home use, because they have a high insecticidal and insect proofing effect on insects and are safe to mammals. However, these activities are not entirely satisfactory to some fields. For example, aerosol spray insecticides for home use are required to contain an active ingredient having both a fast-acting property and a lethal effect, but up to now there have been no practical pyrethroids having the above property and effect at the same time. Therefore, pyrethroid having an excellent fast-acting property and fine lethal effect have been used mixed with each other. Further, in the case of a certain kind of injurious insect in an agricultural field, its resistance to pyrethroid seriously threatens to develop. Because of the above noted background, novel insecticides and insect proofing agents which are much more useful are strongly desired.
DISCLOSURE OF THE INVENTION
The present invention is made to develop a novel compound which can provide a solution to the problems the insecticides and insect proofing agents currently in use have, that is, a novel compound which has a fast-acting property and a lethal effect at the same time, and is high in safety and excellent in every point; to provide a process for manufacturing the same; and to provide insecticides and insect proofing agents which contain the same as an effective ingredient.
After concentrating their energy on this study to achieve the above objects, the present inventors have found novel derivatives of esters of carboxylic acids represented by the following general formula I: ##STR3## wherein: R.sub.1 is an alkyl group having a chain or branched chain of 1 to 4 carbon atoms; and IV; ##STR4##
wherein: consisting of hydrogen, fluorine, chlorine atoms or methyl group; or methylthio groups; or chain; and confirmed that the compounds can be put to practical use, and thus perfected the present invention.
In other words, the present invention of in a first embodiment relates to novel derivatives of esters of carboxylic acids represented by the general formula I. Though there exists optical or geometrical isomers based on the steric structures of the portions of cyclopropanecarboxylic acid and alcohol among esters represented by the general formula I, all such esters are also included by the present invention.
The typical examples of novel derivatives of esters of carboxylic acids represented by the general formula I are as follows, but they are not intended to limit the present invention.
5-propargyl-2-furylmethyl 2,2-dimethyl-3-(3-methoxy-3-oxo-1-propenyl)cyclopropanecarboxylate ##STR5## (2) Compound 2
5-propargyl-2-methyl-3-furylmethyl 2,2-dimethyl-3-(3-methoxy-3-oxo-1-propenyl)cyclopropanecarboxylate ##STR6## (3) Compound 3
2-methyl-3-propargyl-4-oxo-2-cyclopentene-1-yl 2,2-dimethyl-3-(3-methoxy-3-oxo-1-propenyl) cyclopropanecarboxylate ##STR7## (4) Compound 4
4-propargylbenzyl 2,2-dimethyl-3-(3-methoxy-3-oxo-1-propenyl) cyclopropanecarboxylate ##STR8## (5) Compound 5
2,6-dimethyl-4-propargylbenzyl 2,2-dimethyl-3-(3-methoxy-3-oxo-1-propenyl)cyclopropanecarboxylate ##STR9## (6) Compound 6
4-methoxymethylbenzyl 2,2-dimethyl-3-(3-methoxy-3-oxo-1-propenyl)cyclopropanecarboxylate ##STR10## (7) Compound 7
2-fluoro-5-trifluoromethyl-.alpha.-ethynylbenzyl 2,2-dimethyl-3-(3-methoxy-3-oxo-1-propenyl) cyclopropanecarboxylate ##STR11## (8) Compound 8
2-methyl-3-propargyl-4-methylidene-2-cyclopentene-1-yl 2,2-dimethyl-3-(3-ethoxy-3-oxo-1-propenyl)cyclopropanecarboxylate ##STR12## (9) Compound 9
2,6-difluoro-4-methylthiobenzyl 2,2-dimethyl-3-(3-isopropoxy-3-oxo-1-propenyl)cyclopropanecarboxylate ##STR13## (10) Compound 10
2-chloro-4,5-methylenedioxy-.alpha.-ethynylbenzyl 2,2-dimethyl-3-(3-n-butoxy-3-oxo-1-propenyl) cyclopropanecarbo
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Katsuda Yoshio
Minamite Yoshihiro
Nakayama Koji
Dainihon Jochugiku Co., Ltd.
Shippen Michael L.
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