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II type pyrethroid universal hapten compound and synthetic method thereof

A technology for pyrethroids and synthetic methods, which is applied in the fields of chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of many hapten synthesis steps and harsh synthesis conditions, and achieve a simple, fast, and universal synthesis method Strong performance and simple operation steps

Inactive Publication Date: 2009-04-15
INST OF OIL CROPS RES CHINESE ACAD OF AGRI SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There have been some reports on type II pyrethroid hapten compounds and synthetic methods, but these haptens usually have more synthesis steps or harsh synthesis conditions. For example, the hapten reported by John H. Skerritt research group in Australia in 1998 needs to go through 4 steps of reaction Synthesis, the hapten reported by the research group of Professor Bruce D Hammock in the United States in 2005 needs to be synthesized through a two-step reaction under harsh conditions, and the hapten disclosed in the invention patent of Zhu Guonian et al.

Method used

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  • II type pyrethroid universal hapten compound and synthetic method thereof
  • II type pyrethroid universal hapten compound and synthetic method thereof
  • II type pyrethroid universal hapten compound and synthetic method thereof

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Effect test

Embodiment 1

[0024] 1) Dissolve 1.31 g (8 mmol) of succinoyl chloride in 5 mL of dichloromethane to make a 1.6 mol / L solution, and cool to -2°C.

[0025] 2) Dissolve 1.26g (5mmol) of α-cyano-m-phenoxybenzyl alcohol in 5mL of dichloromethane to make a 1mol / L solution, cool to -2°C and slowly add to the reaction flask dropwise, while adding 0.1mL (7mmol) triethylamine, stirring reaction 2 hours after finishing dropwise, reaction temperature is-2 ℃, the raw material triethylamine of reaction: α-cyano m-phenoxybenzyl alcohol: the mol ratio of succinoyl chloride is 1.4:1:1.6. After the reaction, the product α-cyano (3-phenoxyphenyl) methyl-4-chloro-4-carbonyl butyrate mass spectrum molecular ion peak M=343 was measured by gas chromatography-mass spectrometry, and the product It is consistent with the theoretical value of the target compound, which proves that the type II pyrethroid general hapten is successfully synthesized, and the light yellow liquid obtained by purification by vacuum fracti...

Embodiment 2

[0027] 1) Dissolve 0.66 g (4 mmol) of succinoyl chloride in 5 mL of dichloromethane to make a 0.8 mol / L solution, and cool to 4°C.

[0028] 2) Dissolve 0.63g (2.5mmol) of α-cyano-m-phenoxybenzyl alcohol in 3mL of dichloromethane to make a 0.83mol / L solution, cool to 4°C and slowly add it dropwise to the reaction flask, while dropping Add 0.025mL (1.7mmol) triethylamine, stir and react for 1.8 hours after the dropwise addition, the reaction temperature is 4°C, the mol ratio of reaction raw materials triethylamine: α-cyano-phenoxybenzyl alcohol: succinoyl chloride is 0.7:1:1.6. After the reaction, the product α-cyano (3-phenoxyphenyl) methyl-4-chloro-4-carbonyl butyrate mass spectrum molecular ion peak M=343 was measured by gas chromatography-mass spectrometry, and the product It is consistent with the theoretical value of the target compound, which proves that the type II pyrethroid general hapten was successfully synthesized, and the light yellow liquid was purified by vacuum...

Embodiment 3

[0030] 1) Dissolve 0.41 g (2.5 mmol) of succinoyl chloride in 5 mL of dichloromethane to make a 2 mol / L solution, and cool to 0°C.

[0031] 2) Dissolve 0.63g (2.5mmol) of α-cyano-m-phenoxybenzyl alcohol in 3mL of dichloromethane to make a 0.83mol / L solution, cool to 0°C and slowly add to the reaction flask dropwise, while dropping Add 0.025mL triethylamine, stir and react for 2 hours after the dropwise addition, the reaction temperature is 0°C, the molar ratio of the reaction raw materials triethylamine: α-cyano-m-phenoxybenzyl alcohol: succinoyl chloride is 0.7: 1: 1. After the reaction, the product α-cyano (3-phenoxyphenyl) methyl-4-chloro-4-carbonyl butyrate mass spectrum molecular ion peak M=343 was measured by gas chromatography-mass spectrometry, and the product It is consistent with the theoretical value of the target compound, which proves that the type II pyrethroid general hapten was successfully synthesized, and the light yellow liquid was purified by the method of...

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Abstract

The invention relates to a II type pyrethroid general hapten compound applied to the pesticide artificial antigen and antibody preparation field and a synthesizing method thereof. The compound is alpha-cyan (3-phenoxyl phenyl) methyl-4-chlorine-4-carbonyl butyric ester, wherein, alpha-cyano inter phenoxy benzene methanol and succinimide chloride are main raw materials which are respectively dissolved in methylene dichloride; then alpha-cyano inter phenoxy benzene methanol solution is slowly dropped into succinimide chloride solution; simultaneously, triethylamine is added to have a hybrid reaction; through decompression, fractionation and purification after the reaction, the compound is obtained. The invention is easy to realize a covalent binding between hapten and carrier protein, therefore a chemical reaction between terminal acyl chloride structure (-COCl) and amino of carrier protein (-NH2) occurs to prepare artificial antigen; through one step to synthesize hapten compound, the II type pyrethroid general hapten compound applied to the pesticide artificial antigen and antibody preparation field and the synthesizing method thereof have simple operating procedures, simple, convenient and fast synthesizing method.

Description

technical field [0001] The invention relates to selection of a type II pyrethroid general hapten compound used in the field of pesticide artificial antigen and antibody preparation and a synthesis method thereof. Background technique [0002] The problem of pesticide residues has become a hot issue of general concern in today's society. Pyrethroid pesticides are one of the three major categories of insecticides, which have the characteristics of broad insecticidal spectrum, moderate toxicity, and accumulation. With the prohibition or restriction of highly toxic organophosphorus and carbamate pesticides, the use of pyrethroid pesticides has become more and more widespread, and the problem of such pesticide residues has also become increasingly apparent. The problem of excessive pyrethroid pesticide residues is the most common problem in the export trade of agricultural products such as tea in my country. Therefore, monitoring pyrethroid pesticide residues is of great signif...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/38C07C253/30
Inventor 李培武张奇张文谢立华丁小霞姜俊陈小媚
Owner INST OF OIL CROPS RES CHINESE ACAD OF AGRI SCI