Pyrethroid compound as well as preparation method and application thereof

A technology for pyrethroids and compounds is applied in the field of pyrethroid compounds, which can solve the problems of obvious irritation to humans and animals and high toxicity, and achieve the effects of easy industrialization, improved quality and simple technology.

Inactive Publication Date: 2013-03-20
BESTCHEN GUIYANG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In 1980, U.S. Patent US4183948 replaced a chlorine in the part of permethrin with trifluoromethyl, that is, 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2 - When dimethylcyclopropane carboxylic acid is used as the acid part of pyrethroid, its cis-body has excellent insecticidal effect, but it has high toxicity and is obviously irritating and harmful to humans and animals, so it is not suitable for household hygiene drugs

Method used

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  • Pyrethroid compound as well as preparation method and application thereof
  • Pyrethroid compound as well as preparation method and application thereof
  • Pyrethroid compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation Embodiment 1

[0044] Preparation Example 1: Resolution of trans-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid

[0045] In a 500ml four-necked bottle, put 200ml of water, 24.0g of sodium carbonate, racemic trans-3-(2-chloro-3,3,3-trifluoroallyl)-2,2-dimethyl 50.0g of cyclopropane carboxylic acid, stir to dissolve, control the temperature at 20-25°C, add dropwise a solution of 21.0g of D-phenylglycine ethyl ester hydrochloride dissolved in 100ml of water, add dropwise for 1 hour, keep stirring for 1 hour, at this time A white solid was precipitated, filtered by suction, washed with 100 ml of water, and dried by suction. The obtained solid was added to 100ml of 5% hydrochloric acid and stirred to precipitate crystals, filtered by suction, washed with 100ml of water, and dried to obtain trans-dex-3-(2-chloro-3,3,3-trifluoro-1-propenyl )-2,2-dimethylcyclopropanecarboxylic acid 20.0g, dextrorotatory effective body ee value 96%.

preparation Embodiment 2

[0046] Preparation Example 2: Chloroacylation of trans-dex-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid

[0047] In a 500ml four-necked bottle, put the trans-dex-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl obtained in Preparation Example 1 Cyclopropanecarboxylic acid 121.2g, (0.5mol, ee value 96%), dissolved in 200ml toluene, stirred evenly, heated to 40-60°C, added SOCl dropwise 2 72g, (0.6mol), dripped within 2 hours, then raised the temperature to 65°C, and kept the temperature for 1 hour. Heating to 80°C under 0.08MPa negative pressure to remove solvent toluene, then rectifying under 0.09MPa negative pressure, collecting fractions at 70-75°C to obtain trans-dex-3-(2-chloro-3,3,3 -Trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid chloride 123.6g, content 95.2%, yield 90.5%, dextro-trans effective body ee value 96%.

preparation Embodiment 3

[0048] Preparation Example 3: 1-ethynyl-2-methyl-2-pentenyl-(trans-dextrorotatory)-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-di Synthesis of Methylcyclopropane Carboxylate.

[0049] In a 1000ml four-neck flask, put 500g of toluene, 56g of 1-ethynyl-2-methylpenten-2-ol (0.45mol), and 50.0 of pyridine, stir evenly, cool down to 5°C, and prepare dropwise Trans-dex-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid chloride 123.6g (0.45mol) obtained in Example 2 , added dropwise for 2 hours, the dropwise addition was completed, and the reaction was completed at 20° C. for 6 hours. Add 300ml of 5% hydrochloric acid to wash once, add 300ml of water to wash twice, and remove the solvent from the reaction solution under a negative pressure of 0.09MPa. 1-Ethynyl-2-methyl-2-pentenyl-(trans-dextro)-3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2- Dimethylcyclopropane carboxylate, compound (A), has a weight of 153.0 g, a content of 97.0%, and a yield of 95...

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Abstract

The invention discloses a pyrethroid compound as well as a preparation method and an application thereof, and provides a preparation method of the pyrethroid compound 1-acetenyl-2-methyl-2-pentenyl-(trans-dextrorotation)-3-(2-chlorine-3,3,3-trifluoro-1-propenyl)-2, 2-dimethylcyclopropane carboxylic ester, and an application thereof in the aspect of preventing and treating sanitary insect pests. The compound is prepared from trans-dextrorotation-3-(2-chlorine-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropane carboxylic ester and 1-acetenyl-2-methyl-amylene-2-alcohol in an esterifying manner, is one of pyrethroids, and belongs to synthetic organic pesticides. The pyrethroid compound is simple in technique and easy to industrially popularize; the product is used for exterminating family health pests and mosquitoes, flies, german cockroach and the like, has efficient and low-toxicity effects, and is a new pesticide researched for preventing the sanitary insect pests from generating drug resistance on pyrethroid drugs.

Description

technical field [0001] The invention relates to a pyrethroid compound, in particular to a single optically active pyrethroid compound, as well as its preparation method and application. Background technique [0002] Insecticide is a kind of commodity with clear purpose. It is mainly used in two fields of agriculture and household sanitation. Household insecticide not only requires high insecticidal activity, but also requires low toxicity and environmental friendliness. [0003] Pyrethroid compounds—cyclopropane carboxylate products have high insecticidal activity and have been widely used to control pests. In 1986, Zhongxi Pharmaceutical Factory successfully developed a new type of sanitary drug - Zhongxi Aerosolthrin, namely Chlorempenthrin, English name: Chlorempenthrin, chemical name: 1-ethynyl-2-methylpent-2-enyl (RS) -2,2-Dimethyl-3-(2,2-dichlorovinyl)cyclopropanecarboxylate, with trans-permethrinyl chloride and 1-ethynyl-2-methyl-pentene-2 Obtained from the esterifi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/747C07C67/14A01N53/10A01P7/04
Inventor 李国江杨书翰冯顺平杨再勇
Owner BESTCHEN GUIYANG
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