Organic compounds -- part of the class 532-570 series – Organic compounds – Nitriles
Patent
1995-11-17
1999-03-23
Powers, Fiona T.
Organic compounds -- part of the class 532-570 series
Organic compounds
Nitriles
514521, C07C25541
Patent
active
058862072
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/CN95/00002 filed Jan. 4, 1995.
FIELD OF THE INVENTION
The present invention relates to a pyrethroidal pesticide, more particularly, to the Flubrocythrinate optically active compound, their preparations and uses.
BACKGROUND OF THE INVENTION
A new compound of the following structural formula I has been disclosed in Chinese Patent NO. CN 91107318.3 (applicant: Shanghai Zhong Xi Pharmaceutical Co., Ltd.) ##STR1##
The compound of formula I has the common name Flubrocythrinate, and its chemical name is .alpha.-cyano-3-(4-bromophenoxy) benzyl-2-(4-difluoromethoxyphenyl)-3-methylbutyrate.
Flubrocythrinate possesses relatively high insecticidal and miticidal activities and excellent efficacy in comparison with ordinary pyrethroidal pesticides known in prior art, Flubrocythrinate also shows low toxicities towards human and animals and low toxicities towards beneficial insects and animals, in other words, said compound possesses very high insecticidal and miticidal activities and selectivities.
The inventor of the present invention has made efforts in increasing the efficacy and decreasing the dosage of the compound described above. The inventor notes that there are two chiral carbons in the structure formula of compound I, it consists of four optically active isomers. The inventor found, that the efficacy illustrated by an insecticidal and miticidal agents using the racemic form of the compound I as the active ingredient is lower than that using a specific optically active isomer. The dosage of the racemic form of the compound I used is greater than that of a single optically active isomer used, therefore increasing the environmental pollution.
OBJECTION OF THE INVENTION
An aim of the present invention is to provide a powerful insecticidal and miticidal optically active isomeric compound of formula I.
A further objection of the present invention is to provide method for the preparation of some optically active isomers of compound I.
A still further objection of the present invention is to provide applications of said optically active isomers to insecticides and miticides.
SUMMARY OF THE INVENTION
The objections described above are realized on the basis of following conceptions:
The compound Flubrocythrinate possesses four optically active isomers:
1. (S)-.alpha.-Cyano-3-(4-bromophenoxy)benzyl-(S)-2-(4-difluoromethoxyphenyl) -3-methylbutyrate (Ia): ##STR2##
2. (R)-.alpha.-Cyano-3-(4-bromophenoxy)benzyl-(S)-2-(4-difluoromethoxyphenyl) -3-methylbutyrate (Ib): ##STR3##
3. (S)-.alpha.-Cyano-3-(4-bromophenoxy)benzyl)-(R)-2-(4-difluoromethoxyphenyl )-3-methylbutyrate (Ic): ##STR4##
4. (R)-.alpha.-Cyano-3-(4-bromophenoxy)benzyl (R)-2-(4-difluoromethoxyphenyl)-3-methylbutyrate (Id): ##STR5##
Among these four optically active isomers, the compound Ia, Ib or the racemic mixture of (S,S)-(Ia) and (R,R)-(Id) (this racemic mixture is thereafter referred to A), or the mixture of the isomers thereof possesses apparent pesticidal and miticidal activities: ##STR6##
The optically active isomer Ia possesses the strongest pesticidal and insecticidal activities.
The preparative method involved in the present invention includes the following steps:
Reaction equations: ##STR7##
1. Preparation of the compound of formula Ia:
(1) Preparation of (S)-2-(4-difluoromethoxyphenyl)-3-methylbutyric acid:
1 part of 2-(4-difluoromethoxyphenyl)-3-methylbutyric acid is dissolved in 1-5 parts (by weight) of solvent comprising an organic solvent such as an aliphatic alcohol, an aromatic hydrocarbon, a keton, a halogenated hydrocarbon, an ether, an ester, or an aliphatic hydrocarbon, etc. After the dissolution is completed, 1-3 moles of resolving agent, an optically active organic base such as 1-(4-nitrophenyl)-2-dimethylamino-1,3-propanediol, quinine, substituted .alpha.-aminoethylbenzene and the like, is added. The mixture thus obtained is stirred at -50.degree. C. to 200.degree. C., preferably at 0.degree. C. to reflux temperature of the solvent, for 0.1-100 hours, preferably for 1-10 hours. After the reactio
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English translation of Chinese patent 1063681, Aug. 19, 1992.
Jin Weigao
Sun Guanhe
Xie Hongyue
Zuo Lin
Powers Fiona T.
Shanghai Zhongxi Pharmaceutical Co. Ltd.
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