Radioisotope carbon-14 labelled pesticide chlopyrifos, and synthetic method thereof

Abstract

The invention belongs to the field of radiochemical synthesis, and more specifically relates to radioisotope carbon-14 labelled pesticide chlopyrifos, and a synthesis method thereof. The synthesis method comprises following steps: a metal organic reagent is reacted with [14C] carbon dioxide so as to obtain 5-benzyloxy[carbonyl-14C] pentanoic acid; amidation, debenzylation, and cyclization reactionare adopted so as to realize conversion into [carbonyl-2, 6-14C2] glutarimide; aromatization, chlorination, and hydrolysis are adopted, and an obtained hydrolysate and diethyl thiophosphoryl chlorideare subjected to nucleophilic substitution so as to obtain the carbon-14 labelled pesticide chlopyrifos. The synthetic method is capable of avoiding defects in the prior art; the reaction raw materials are easily available; the reaction conditions are mild; production cost is low; the obtained carbon-14 labelled pesticide chlopyrifos can be taken as a radioactive tracer, can be used in tracing ofpollution evolution rules such as migration conversion, metabolism degradation, and absorption enrichment of chlopyrifos in the environment and in vivo, and can be used for providing technical support for comprehensive evaluation of the biological safety of chlopyrifos; and in addition, the synthesis method is capable of providing reference for preparation of building blocks containing C-14.

Description

technical field [0001] The invention belongs to the field of radiochemical synthesis, and in particular relates to a radioactive isotope carbon-14 labeled insecticide chlorpyrifos and a synthesis method thereof. Background technique [0002] Chlorpyrifos (Chlorpyrifos; O,O-diethyl-O-(3,5,6-trichloro-2-pyridyl)phosphorothioate) belongs to the acetylcholinesterase inhibitors, is the current organophosphorus insecticides The pesticide species with the broadest market prospect and the greatest potential. It is a high-efficiency and low-toxic insecticide first discovered by Dow Chemical Company in 1962. It has stomach poisoning, contact killing, and fumigation effects, and has good control effects on various chewing and piercing mouthparts pests on various crops. . Currently, chlorpyrifos is considered to be the best choice to replace five highly toxic organophosphorus pesticides, methamidophos, parathion, methyl parathion and monocrotophos. In the more than 50 years since the...

AI Technical Summary

Problems solved by technology

[0008] The main technical defects and deficiencies in the synthesis method of carbon-14 labeling chlorpyrifos in the literature are as follows: use highly poisonous potassium cyanide / sodium and chlorine in the reaction; when intermediate 12 is converted into [1,5- 14 C 2 ] glutaronitrile (5) requires high temperature and high pressure reaction conditions (280 ° C); 14 C] cyanide is a synthetic radioisotope raw material; thus the synthetic raw material of this method is difficult to obtain, the synthetic risk is large, and the synthetic cost is high

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