四唑虫酰胺及其关键中间体的合成方法综述

A Review on Synthetic Methods of Tetraniliprole and Key Intermediates

综述了由拜耳作物科学公司开发的新型双酰胺类杀虫剂四唑虫酰胺(Tetraniliprole)的合成方法,主要包括缩合法、胺解法和环化法等3种方法,且对这些方法所涉及的关键中间体的合成也进行了简要概述。其中,缩合法,特别是以关键中间体N,3-二甲基-2-氨基-5-氰基苯甲酰胺和1-(3-氯吡啶-2-基)-3-(5-三氟甲基-2H-四氮唑-2-亚甲基)吡唑-5-甲酸在碱和甲磺酰氯作用下直接合成四唑虫酰胺的合成路线,具有原料易得、产率高和易于操作等优点,可能是目前制备四唑虫酰胺的最佳合成工艺。

Synthetic methods of tetraniliprole developed by Bayer CropScience as the new bisamide insecticide were reviewed,including three methods:condensation,aminolysis and cyclization,and the synthesis of key intermediates involved in these methods was also briefly summarized.Among them,the condensation method,especially the route of the key intermediates N,3-dimethyl-2-amino-5-cyanobenzamide and 1-(3-chloropyridin-2-yl)-3-(5-Trifluoromethyl-2H-tetrazolium-2-methylene)pyrazole-5-carboxylic acid under the action of alkali and methanesulfonyl chloride,had the advantages of easy availability of raw materials,high yield and easy operation,which may be the best synthetic process for preparing tetrazolidene at present.