Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Ester doai
Patent
1986-09-16
1989-07-04
Robinson, Allen J.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Ester doai
A01N 3734
Patent
active
048451266
DESCRIPTION:
BRIEF SUMMARY
CROSS REFERENCE TO RELATED APPLICATIONS
This application is a national phase of PCT/HU86/00004 and is related to PCT/HU 86/00003, filed 16 January 198 and based upon Hungarian 158/85 of 16 January 1985 and 74/86 of 8 January 1986.
FIELD OF THE INVENTION
This invention relates to insecticidal compositions comprising more than one pyrethroid active ingredient of the Formula /I/ ##STR2## the use thereof, the active ingredients and a process for the preparation of the same.
BACKGROUND OF THE INVENTION
In the present specification the spatial configuration of the substituents related to the chiral carbon atom denoted with ".alpha." is characterized by "S" and "R", respectively. The designations "cis" and "trans", respectively, mark the position of the substituents attached to carbon atom "3" of the cyclopropane ring related to the spatial configuration of the substituents of carbon atom "1". The absolute spatial configuraton of the substituent attached to carbon atom "1" is denoted with the prefix "1R" and "1S", respectively.
In the present specification the various enantiomers and enantiomer-pairs are designated with the following abbreviations:
It is known that pyrethroids of the Formula /I/ (known under the generic name "cypermethrin") belong to the valuable family of synthetic pyrethroids and are useful as insecticide (Hungarian Pat. No. 170,866). These compounds may be prepared by reacting m-phenoxy-benzaldehyde cyanohydrine with the corresponding cyclopropane carboxylic acid chloride in the presence of a base [Pestic. Sci. 6, 537, . . . 1975]. The product thus obtained consists of eight stereoisomers i.e. of a mixture of four enantiomer-pairs. If a 60:40 mixture of the corresponding trans and cis cyclopropane carboxylic acid chlorides is used, the mixture contains 18-19% of enantiomer-pair Ia, 21-22% of enantiomer-pair Ic, 26-27% of enantiomer-pair Ib and 33-34% of enantiomer-pair Id.
According to prior art the steroisomers of cypermethrin show different biological activity. It is generally accepted that the activity of molecules comprising cis cyclopropane carboxylic acids is superior to that of the corresponding trans derivatives [Pest. Sci. 7, 273, 1976].
In the comparative biological tests of various pyrethroids [Pest. Sci. 9, 112-116 1978] the cis and trans stereoisomers--including the cypermethrin stereoisomer-pairs--were evaluated together.
The comparative tests were carried out on Musca domestica L. and Phaedon cochleariae Fab species. Concerning the chloro derivatives from the trans isoomers activity data of 1RtransS Ig and 1RtransR were disclosed. The said data show that--while the 1RtransS isomer possesses a strong activity--the 1RtransR isomer is considerably less active [according to the test the activity related to bioresmetrine 100 amounts to 1400 and 81, respectively, on Musca domestica and to 2200 and 110, respectively, on Phaedon cochleariae]. It was disclosed further that the activity of a mixture of both tested isomers was lower than the calculated value. Thus the isomers showed an antagonism rather than the expected synergism and the rate of antagonism amounted to 1.42 and 1.46 on house fly and mustard beetle, respectively.
As a result of the said test and publications the trans isomers and mixtures thereof were pushed to the background of biological interest and research was focused to active cis derivatives and mixtures thereof. This lead to the development of alphamethrin (isomer mixture of 1RcisS and 1ScisR Ia) of the chloro derivatives) and decamethrin [comprising the 1RcisS isomer (If) of the bromo derivatives].
Similar data were set forth for the bromo derivative; on mustard beetle the rate of antagonism amounts to 1.48.
DESCRIPTION OF INVENTION
According to an aspect of the present invention there is provided a synergistic insecticidal composition containing more than one active ingredients and being harmless to environment characterized by comprising in an amount of from 0.001 to 99% by weight of a synthetic pyrethroid of the Formula /I/--namely substantially only t
REFERENCES:
patent: 4024163 (1977-05-01), Elliott et al.
patent: 4031239 (1977-06-01), Schrider
patent: 4181735 (1980-01-01), Smolikowski et al.
patent: 4404223 (1983-09-01), Matthewson
patent: 4524150 (1985-06-01), Adalsteinsson
Bertok Bela
Botar Sandor
Gajari Antal
Hegedus Agnes
Hidasi Gyorgy
Chinoin Gyogyszer - es Vegyeszeti Termekek Gyara Rt.
Dubno Herbert
Myers Jonathan
Robinson Allen J.
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