Synthesis method of radioisotope carbon-14 labeled imidacloprid

A technology of radioisotope and synthesis method, applied in the field of radiochemical synthesis, can solve the problem that the labeling synthesis method has not been publicly reported, and achieve the effects of simple and easy synthesis technical route, high radiochemical purity and mild reaction conditions

Inactive Publication Date: 2019-07-02
上海启甄环境科技有限公司
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Problems solved by technology

[0003] Internationally, the synthesis of carbon-14-labeled imidacloprid is mainly completed by Bayer in Germany. The labeling site is the methylene group and the carbon atom at the 2-position of the imidazoline ring in the imidacloprid molecule. However, the labeling synthesis method has not been publicly reported for reasons of confidentiality.

Method used

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  • Synthesis method of radioisotope carbon-14 labeled imidacloprid
  • Synthesis method of radioisotope carbon-14 labeled imidacloprid
  • Synthesis method of radioisotope carbon-14 labeled imidacloprid

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[0021] The following examples are given to illustrate the present invention. The implementation examples are only used to further illustrate the present invention, and do not represent the protection scope of the present invention. Non-essential modifications and adjustments made by others according to the present invention still belong to the protection scope of the present invention.

[0022] At room temperature and under the protection of argon, add anhydrous lithium chloride (420 mg) into the reaction flask, heat with a heat gun, and repeat the vacuum-filling operation 5 times to thoroughly dry the lithium chloride. Add magnesium chips (480 mg), replace with argon three times, add anhydrous THF (10 mL), and stir until lithium chloride is completely dissolved. Add diisobutylaluminum hydride (1 M, 160 μL) and stir at room temperature for 5 min. Cool down to 0°C, slowly add 2-chloro-5-bromopyridine (1.540 g) anhydrous THF solution (10 mL) dropwise, and continue stirring unti...

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Abstract

The invention belongs to the field of radiochemical synthesis, and specifically relates to a synthesis method of the radioisotope carbon-14 labeled imidacloprid (1-(6-chloro-3-pyridyl[<14>C]methyl)-N-nitroimidazole-2-imine). The method has the following characteristics: carbon-14 labeled barium carbonate is used as the radioisotope raw material, 6-chloro-pyridine-3-[<14>C]formic acid is obtained by the reaction of an organometallic reagent and [<14>C] carbon dioxide, then 6-chloro-pyridine-3-[<14>C]formic acid is subjected to reactions of reduction, bromination and condensation to obtain the methylene carbon-14 labeled imidacloprid, and the total number of reaction steps are four. The radioisotope C-14 labeled imidacloprid prepared by the method has high specific activity and radiochemicalpurity, and can be used as a radioactive tracer for the study of metabolic residues of imidacloprid in plants and animals and the study of the environmental behavior of imidacloprid in soil and water. At the same time, the method establishes a preparation method of some synthetic blocks containing carbon-14.

Description

technical field [0001] The invention belongs to the field of radiochemical synthesis, in particular to a radioactive isotope carbon-14 labeled imidacloprid (1-(6-chloro-3-pyridine [ 14 C] methyl)- N - the synthetic method of nitroimidazole-2-imine). Background technique [0002] Imidacloprid (Imidacloprid; 1-(6-chloro-3-pyridylmethyl)- N -Nitroimidazole-2-imine) is a high-efficiency nicotinic systemic insecticide developed and listed by Bayer Company of Germany in 1991. It acts on the nicotinic acid acetylcholinesterase receptor of pests and has high efficiency and broad spectrum. , low toxicity, safety and high selectivity. It has passed the registration test requirements of hundreds of crops in more than 120 countries and has been used in agricultural production for 25 years. As the consumption of imidacloprid continues to increase, the possible problems of food safety, environmental pollution and human health have attracted more and more attention from researchers a...

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/06
CPCC07B2200/05C07D401/06
Inventor 杨征敏叶庆富许亚军张贵华李霄
Owner 上海启甄环境科技有限公司
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