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Procymidone hapten and synthetic method and application thereof

A synthesis method, the technology of procymidone, is applied in the direction of material inspection products, test food, instruments, etc., to achieve the effects of simple reaction operation, synthetic cost advantages, and easy control of reaction conditions.

Inactive Publication Date: 2019-07-02
SHENZHEN BIOEASY BIOTECHNOLOGY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, at present, there is no relevant report on procymidone hapten in China

Method used

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  • Procymidone hapten and synthetic method and application thereof
  • Procymidone hapten and synthetic method and application thereof
  • Procymidone hapten and synthetic method and application thereof

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preparation example Construction

[0041] In the second aspect, the present invention also provides a method for synthesizing the above-mentioned procymidone hapten, comprising the following steps:

[0042] S1, providing an intermediate A having the structural formula ;

[0043] S2, providing an intermediate B having the structural formula , wherein, n is the number of -CH2 groups, and n is an integer of 1-5;

[0044] S3, the intermediate A and intermediate B are reacted to obtain compound 5, and the compound 5 has the structural formula , wherein, n is the number of -CH2 groups, and n is an integer of 1-5;

[0045] S4, the compound 5 is subjected to a condensation reaction to obtain a compound 6, and the compound 6 has the structural formula , wherein, n is the number of -CH2 groups, and n is an integer of 1-5;

[0046] S5, subjecting the compound 6 to a hydrolysis reaction to obtain the procymidone hapten.

[0047] According to the structural characteristics of procymidone, the present invention ratio...

Embodiment 1

[0067] A synthetic method of procymidone hapten, comprising the steps of:

[0068] S1, providing intermediate A, which is 1,2-dimethyl-1,2-cyclopropane anhydride;

[0069] The preparation method of the intermediate A is:

[0070] (1) Add 100mL toluene to a 250mL three-necked flask, add 0.2mol sodium hydride in an ice-water bath, stir for 30 minutes, then slowly add 0.1mol α-methyl chloroacrylate and 0.12mol methyl methacrylate dropwise, and the addition is complete After the reaction at room temperature overnight, after the reaction is complete, add 10mL of ethanol, stir for 10-15min, then add 200mL of water, adjust the pH of the solution to 5-6 with dilute hydrochloric acid, extract with 200mL ethyl acetate, collect the ethyl acetate layer, acetic acid The ethyl ester layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then distilled under reduced pressure to remove toluene and ethyl acetate, and the residue was purified by distillation under redu...

Embodiment 2

[0080] A synthetic method of procymidone hapten, comprising the steps of:

[0081] S1, providing intermediate A, which is 1,2-dimethyl-1,2-cyclopropane anhydride;

[0082] The preparation method of the intermediate A is:

[0083] (1) Add 100mL of dichloromethane into a 250mL three-necked flask, add 0.5mol of sodium hydride in an ice-water bath, stir for 30min, then slowly add 0.1mol of α-methyl chloroacrylate and 0.1mol of methyl methacrylate dropwise, drop After the addition, react overnight at room temperature. After the reaction, add 20 mL of ethanol, stir for 10-15 minutes, add 200 mL of water, adjust the pH of the solution to 5-6 with dilute hydrochloric acid, extract with 200 mL of ethyl acetate, and collect the ethyl acetate layer , the ethyl acetate layer was washed with saturated brine, dried over anhydrous sodium sulfate, dichloromethane and ethyl acetate were removed by vacuum distillation, and the residue was purified by oil pump vacuum distillation to obtain 1,2-...

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Abstract

The invention discloses a procymidone hapten and a synthetic method and application thereof. The synthetic method comprises the following steps: (1) alpha-chloromethyl acrylate and methyl methacrylateare used as starting materials to synthesize 1,2-dimethyl-1,2-cyclopropane dicarboxylic methyl ester; 1,2-dimethyl-1,2-cyclopropane dicarboxylic methyl ester undergoes hydrolysis and intramolecular condensation to generate 1,2-dimethylcyclopropane-1,2-dicarboxylic acid anhydride; (2) 3-chloro-5-nitrophenol and a compound 3 are used as raw materials to synthesize an intermediate with an arm, and the intermediate is subjected to a reduction reaction to obtain an intermediate B; and (3) 1,2-dimethylcyclopropane-1,2-dicarboxylic acid anhydride and the intermediate B undergo two times of condensation reaction for cyclization and one time of hydrolysis reaction to obtain the final target product. In the invention, characteristic structure of procymidone is retained in the synthesized procymidone hapten such that the immunogenicity of the procymidone hapten is obviously enhanced, and the procymidone hapten also has a carboxyl group capable of coupling with a carrier, thus providing a foundation for subsequently building various immunoassay methods of procymidone.

Description

technical field [0001] The invention relates to the technical field of food safety detection, in particular to a procymidone hapten and its synthesis method and application. Background technique [0002] Procymidone, also known as Procymidone, Procymidone, Procymidone, etc., is a low-toxicity fungicide with protective and therapeutic effects, long-lasting effect, and resistance to rain; it can be used to control cucumbers Botrytis, eggplant, tomato, onion, etc., stem rot of lettuce, pepper, rape sclerotinia, etc., also used for antiseptic preservation of citrus, banana, apple, pear, peach and other fruits during storage. A small amount of pesticide residues will not cause acute poisoning, but long-term consumption of vegetables with excessive pesticide residues may have certain adverse effects on human health. Recently, the country has often exposed cases of excessive procymidone in leeks and garlic sprouts. [0003] Existing procymidone detection methods mainly include hig...

Claims

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Application Information

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IPC IPC(8): C07D209/52G01N33/531G01N33/02
CPCC07D209/52G01N33/02G01N33/531
Inventor 杨星星李细清付辉王西丽陈允玲黄永健王炳志马涛严义勇周巧妮
Owner SHENZHEN BIOEASY BIOTECHNOLOGY CO LTD
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