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A novel chemical modification of thiomethrin and its preparation method and application

A technology of chemical modification and thiomethrin, applied in chemical instruments and methods, preparation of organic compounds, botany equipment and methods, etc., can solve human and animal health threats, adverse effects on children's health, interference with biological functions, etc. problems, achieve good application prospects, solve the problem of drug resistance, and improve the effect of metabolic stability

Active Publication Date: 2021-05-28
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, more and more studies have found that pyrethroids can interfere with the normal function of organisms and pose a considerable threat to human and animal health
Studies have shown that long-term exposure to pyrethroid-containing environments will have adverse effects on the health of humans, especially children
Moreover, with the long-term single use of some traditional pyrethroid insecticides in large quantities, pests such as mosquitoes and flies have produced obvious drug resistance to pesticides, so a new type of structure that improves metabolic stability and reduces environmental toxicity is needed. pesticide compound

Method used

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  • A novel chemical modification of thiomethrin and its preparation method and application
  • A novel chemical modification of thiomethrin and its preparation method and application
  • A novel chemical modification of thiomethrin and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Embodiment 1 Preparation of Novel Thiolthrin Chemical Modification (LCA-COS-01)

[0037] 1. The preparation of novel thiothrin chemical modification (LCA-COS-01), comprising the following steps:

[0038] (1) First weigh 200mg (0.824mmol) of permethrin in a 50mL round-bottomed flask, and under nitrogen protection, use a syringe to measure 15mL of ultra-dry anhydrous dichloromethane in the flask and stir After it is completely dissolved, add 0.210mL (2.473mmol) of oxalyl chloride three times the amount, stir for about 30min, then add 0.1mL of anhydrous grade N,N-dimethylformamide (DMF) with a 1mL syringe , the reaction will produce a large number of bubbles, and then react at room temperature for 1h;

[0039] (2) The reaction-activated product in the round-bottomed flask after the reaction for 1h is rotary-evaporated and dried in a vacuum rotary evaporator, and during the operation, the external air is reduced as far as possible from entering the round-bottomed flask, an...

Embodiment 2

[0045] Embodiment 2 Preparation of Novel Thiolthrin Chemical Modification (LCA-COS-02)

[0046] 1. The preparation of novel thiothrin chemical modification (LCA-COS-02), comprising the following steps:

[0047] (1) First weigh 200mg (0.824mmol) of permethrin in a 50mL round-bottomed flask, and under nitrogen protection, use a syringe to measure 15mL of ultra-dry anhydrous dichloromethane in the flask and stir After it is completely dissolved, add 0.210mL (2.473mmol) of oxalyl chloride three times the amount, stir for about 30min, then add 0.1mL of anhydrous grade N,N-dimethylformamide (DMF) with a 1mL syringe , the reaction will produce a large number of bubbles, and then react at room temperature for 1 hour;

[0048] (2) The reaction-activated product in the round-bottomed flask after the reaction for 1h is rotary-evaporated and dried in a vacuum rotary evaporator, and during the operation, the outside air is reduced as far as possible from entering the round-bottomed flask,...

Embodiment 3

[0054] Embodiment 3 Preparation of Novel Thiolthrin Chemical Modification (LCA-COS-03)

[0055] 1. The preparation of novel thiothrin chemical modification (LCA-COS-03), comprising the following steps:

[0056] (1) First weigh 200mg (0.824mmol) of permethrin in a 50mL round-bottomed flask, and under nitrogen protection, use a syringe to measure 15mL of ultra-dry anhydrous dichloromethane in the flask and stir After it is completely dissolved, add 0.210mL (2.473mmol) of oxalyl chloride three times the amount, stir for about 30min, then add 0.1mL of anhydrous grade N,N-dimethylformamide (DMF) with a 1mL syringe , the reaction will produce a large number of bubbles, and then react at room temperature for 1 hour;

[0057] (2) The product activated in the previous step in the round-bottomed flask after the reaction for 1 h is dried by rotary evaporation in a vacuum rotary evaporator, and during the operation, reduce the external air from entering the round-bottomed flask as much a...

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Abstract

The invention discloses a novel thiomethrin chemical modification and its preparation method and application. The present invention mainly transforms a terminal chlorine atom and an ester group on the transfluthrin, replaces a terminal chlorine atom with a trifluoromethyl group, and replaces the ester group with a thiol ester group structure, A series of novel thiomethrin compound structures containing a thiol structure are formed. These novel thiomethrin chemical modifications can improve metabolic stability and reduce environmental toxicity, and have certain insecticidal effects on larvae. Phenethrin is basically at the same concentration level, showing a mosquito-killing effect similar to that of bifenthrin, and can effectively solve the serious problem of outstanding resistance to existing pyrethroid insecticides. In addition, the invention has the advantages of simple reaction process, few reaction steps, high synthesis yield, short reaction cycle, good repeatability and the like.

Description

technical field [0001] The invention belongs to the technical field of pesticides for structure modification of medicine small molecules. More specifically, it relates to a novel thiomethrin chemical modification and its preparation method and application. Background technique [0002] The hot and humid environment in summer brings good conditions for the breeding and infestation of mosquitoes. Mosquitoes, as one of the "four pests", have brought great distress to people's daily life. Not only the buzzing of mosquitoes will affect people's daily rest, work and study, but also people are usually indoors or outdoors. It is easy to be bitten by adult female mosquitoes, which can easily cause skin redness, swelling, pain and discomfort. A more serious problem is that mosquitoes can transmit as many as 80 kinds of diseases such as dengue fever, Japanese encephalitis, yellow fever, malaria and filariasis. Therefore, killing mosquitoes and avoiding mosquitoes is an important mea...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C327/24C07D307/38C07D333/18C07C61/40C07C51/60A01N53/06A01N53/04A01N53/08A01P7/04A01P17/00
Inventor 赵肃清张炳杰高美婷梁汉英方颖琳冯冬燕钟颖颖江政云杨洋朱秋雁洪为谦
Owner GUANGDONG UNIV OF TECH
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