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Cycloprothrin optical activity isomer, preparation method and uses

A technology of promethrin and its isomers, which is applied in the field of photoactive isomers, preparation and application of promethrin, can solve the problems of low activity and phytotoxicity, so as to improve drug efficacy and save raw materials , Improve the effect of economic and social benefits

Inactive Publication Date: 2007-05-30
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In terms of biological activity, some chiral forms show high insecticidal, acaricidal, bactericidal or herbicidal activities, while their enantiomers show low activity or phytotoxicity.

Method used

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  • Cycloprothrin optical activity isomer, preparation method and uses
  • Cycloprothrin optical activity isomer, preparation method and uses
  • Cycloprothrin optical activity isomer, preparation method and uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Example 1 Preparation of chiral 1-(4-ethoxyphenyl)-2,2-dichlorocyclopropane-1-carboxylic acid

[0037] Under the reaction conditions of 40°C, the racemic 1-(4-ethoxyphenyl)-2,2-dichlorocyclopropane-1-carboxylic acid (3.0g) was mixed with S-(-)-α -Methylbenzylamine (1.5 mL) or R-(+)-α-methylbenzylamine (1.5 mL) was reacted in a solvent of ethyl acetate (25 mL). The reaction continued for about 4 days, and the carboxylic acid amine salt crystals were obtained by filtration. The obtained crystals were crystallized several times in ethyl acetate at room temperature (15-25° C.), and finally needle-shaped crystals were obtained. The crystals were dissolved in ethanol, and 1N dilute hydrochloric acid was added thereto. After a period of time, R-(-)-1-(4-ethoxyphenyl)-2,2-dichlorocyclopropane-1-carboxylic acid [α] D 22.6 =-67.3580 (C.1.0, CHCl 3 , 589nm) or crystals of S-(+)-1-(4-ethoxyphenyl)-2,2-dichlorocyclopropane-1-carboxylic acid [α] D 24.3 =66.5620 (C.1.0, CHCl 3...

Embodiment 2

[0038] Embodiment 2 prepares S-(-)-2-hydroxyl-2-(3-phenoxyphenyl) acetonitrile

[0039] Racemic acetylated 2-hydroxy-2-(3-phenoxyphenyl)acetonitrile (38 mg, 0.14 mmol), butanol (12 mg), and lipase from Pseudomonas sp. (4 mg) were dissolved in isopropyl ether ( 3ml), stirred under the condition of 35°C, followed by dot plate, and after about 8 hours, the lipase was filtered off. After separation by column chromatography, S-(-)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrile was obtained with a yield of 80%. 1 HNMR (CDCl 3 , 300MHz) δ=7.43-7.04(m, 9H), 6.38(s, 1H), 2.16(s, 3H).[α] D 27.8 =-20.3475 (C.0.8, CHCl 3 , 589nm), ee=96%.

Embodiment 3

[0040] Embodiment 3 prepares R-(+)-2-hydroxyl-2-(3-phenoxyphenyl) acetonitrile

[0041] Extract (R)-alcohol nitrilase (400mg) from bitter almond, 10mL of 0.1M citrate buffer solution with pH=5.4, potassium cyanide (98mg), glacial acetic acid (120mg) and 3-phenoxyphenyl Formaldehyde (198mg, 1mmol), dissolved in 10mL of isopropyl ether, was reacted for 3 days at a reaction temperature of 0°C, and R-(+)-2-hydroxyl-2-(3-phenoxyphenyl) was isolated Acetonitrile, 78% yield. 1 H NMR (CDCl 3 , 300MHz) δ=7.43-7.04(m, 9H), 6.38(s, 1H), 2.16(s, 3H).[α] D 25.8 =22.3475 (C.1.0, CHCl 3 , 589nm), ee=93%.

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Abstract

The invention discloses a cyanoethylmethrin photoactive isomer, making method and utility with structural formula on the right, which is characterized by the following: simplifying the making method; improving quantity grade of insecticidal activity of alfalfa aphid 2-year middle larva obviously.

Description

technical field [0001] The present invention relates to various photoactive isomers of promethrin, preparation method and insecticidal application containing these photoactive isomers. Background technique [0002] In 1978, Cycloprothrin was invented by the Commonwealth Scientific and Industrial Research Organization (CSIRO) of the Australian National Research Organization, and a new pyrethroid developed by Nippon Kayaku Corporation under the experimental code NK-8116 pesticides. The trade name of promethrin raceme is Cyclosal, which is a low-toxicity, high-efficiency, broad-spectrum pyrethroid insecticide. The drug has low toxicity to fish and mammals, and has no phytotoxicity to many crops under the recommended dosage. As a kind of contact insecticide, the racemate of promethrin has medium persistent effect and has some special activities, such as avoidance and antifeedant. Since 1979, the results of a large number of tests in many countries have shown that the drug has...

Claims

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Application Information

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IPC IPC(8): C07C255/39A01N53/06A01P7/00A01P5/00
Inventor 姜标汪桦
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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