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Method for synthesizing chiral (R, S) fluvalinate and application of chiral (R, S) fluvalinate to control of bee mites

A technology of cyflumethrin and a synthesis method is applied in the field of synthesis of chiral compounds, and can solve the problems of the intermediate S-cyanohydrin with numerous procedures, complicated operation, low ee%, etc., and achieves less dosage, simple operation, The effect of avoiding pollution

Active Publication Date: 2012-01-18
四川彭山汪氏动物保健有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The present invention aims to solve the problems of the preparation of the intermediate S-cyanohydrin in the traditional process of synthesizing chiral (R,S) fluvalinate with many steps, complicated operation and low ee%

Method used

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  • Method for synthesizing chiral (R, S) fluvalinate and application of chiral (R, S) fluvalinate to control of bee mites

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1 Preparation of Chiral (R,S) Fluvalinate

[0026] First add 0.5g (1.88mmol) of S-cyanohydrin acetate to the Erlenmeyer flask, then add 87ul (0.94mmol) of BuOH, 0.05mg of Candida antarctica lipase (NOVO 435) and 10ml of isopropyl ether, place in Shake in a shaker at 10°C for 72h. Then the reaction solution was concentrated and dried, dissolved with 20ml of mixed solution (composed of 6ml of water, 14ml of methanol, and 6ml of benzene), separated and removed from the lower layer solution, and mixed with 10ml of benzene and methanol (volume ratio of benzene and methanol was 7 :3) Extract twice, evaporate part of the methanol, add EA to remove the water layer, and dry the EA layer to obtain 0.06 g of S-cyanohydrin.

[0027] Dissolve 1.31g (0.00444mol) chrysanthemic acid with appropriate amount of EA first, then add the mixed solution into 1.0g (0.00444mol) cyanohydrin and stir in ice bath. Then add 0.90g (0.00444mol) DCC and 0.05g (0.00444mol×10%) DMAP successiv...

Embodiment 2

[0028] Example 2 Preparation of Chiral (R,S) Fluvalinate

[0029] First add 0.5g (1.88mmol) of S-cyanohydrin acetate to the Erlenmeyer flask, then add 87ul (0.94mmol) of BuOH, 0.05g of lipase PS and 10ml of isopropyl ether, and shake in a shaker at 35°C for 5h . Then the reaction solution was concentrated and dried, dissolved with 20ml of mixed solution (composed of 6ml of water, 14ml of methanol, and 6ml of benzene), separated and removed from the lower layer solution, and mixed with 10ml of benzene and methanol (volume ratio of benzene and methanol was 7 :3) Extract twice, evaporate part of the methanol, add EA to remove the water layer, and dry the EA layer to obtain 0.04 g of S-cyanohydrin.

[0030] Dissolve 0.65g (0.00222mol) chrysanthemic acid with appropriate amount of EA first, then add the mixed solution to 0.5g (0.00222mol) cyanohydrin and stir in ice bath. Add 0.4g (0.00222mol) DCC and 0.03g (0.00233mol×10%) DMAP successively and stir in an ice bath for 4h. Fil...

Embodiment 3

[0031] Example 3 Preparation of Chiral (R,S) Fluvalinate

[0032] First add 0.5g (1.88mmol) of S-cyanohydrin acetate to the Erlenmeyer flask, then add 87ul (0.94mmol) of BuOH, 0.005g of Candida antarctica lipase (NOVO 435) and 10ml of isopropyl ether, place in Shake in a shaker at 20°C for 48h. Then the reaction solution was concentrated and dried, dissolved in 20ml of a mixed solution (composed of 6ml of water, 14ml of methanol, and 6ml of benzene), and separated to remove the lower layer solution. ， Extract twice with 10 ml of a mixture of benzene and methanol (volume ratio of benzene and methanol is 7:3), distill off part of the methanol, add EA to remove the water layer, dry the EA layer and concentrate to obtain 0.06 g of S-cyanohydrin.

[0033] Dissolve 1.31g (0.00444mol) chrysanthemic acid with an appropriate amount of benzene, then add the mixed solution to 1.0g (0.00444mol) cyanohydrin and stir in a water bath at 20°C. Then add 0.90g (0.00444mol) DCC and 0.05g (0....

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Abstract

The invention discloses an application of a chiral (R, S) fluvalinate to the control of bee mites, and belongs to the field of the synthesis of chiral compounds. The method comprises the following steps of: a, catalyzing S-cyanohydrin acetate by using lipase in an organic system, and stirring for 5 to 72h at the temperature of between 10 and 35 DEG C to obtain S-cyanohydrin; and b, condensing the S-cyanohydrin and R-chrysanthemic acid at the temperature of between 0 and 20 DEG C in an nonpolar organic system by a dicyclohexylcarbodiimide (DDC) method and an acyl chloride method to obtain the chiral (R, S) fluvalinate. The chiral (R, S) fluvalinate prepared by the method is applied to killing of the bee mites in honeycombs, the method for synthesizing the chiral (R, S) fluvalinate is simple and high in yield, the effect of controlling the bee mites is remarkable, the using amount of pesticides is small, and the environmental pollution caused by useless antipodes can be avoided.

Description

technical field [0001] The invention belongs to the field of synthesis of chiral compounds, and in particular relates to a synthesis method of chiral (R, S) fluvalinate and its application in preventing and controlling bee mites. Background technique [0002] The common name of fluvalinate is Fluvalinate, also known as Mavrik, Mapolik, etc. Pyrethroid insecticides belonging to the class of non-cyclopropane carboxylic acids, containing two isomeric components, namely (RS)-α-cyano-3-phenoxybenzyl N-(2-chloro-α, α-α-Trifluoro-p-tolyl)-D-(R)valine ester, the active ingredient of which is (S)-α-cyano-3-phenoxybenzyl N-(2-chloro- α,α-α-trifluoro-p-tolyl)-D(R)-valine, referred to as (R,S)fluvalinate. [0003] Fluvalinate is mainly used in the control of major pests including Lepidoptera, Coleoptera, Homoptera, Diptera and Thysanoptera on cotton, fruit trees, vegetables, corn, tea, tobacco and other crops. Pests such as housefly, Culex palustris, German cockroach, etc. are also e...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P13/00A01N37/44A01P7/02
Inventor 陆群敖绍川伍金元姚佳
Owner 四川彭山汪氏动物保健有限责任公司