Mannich反应合成噻虫胺与噻虫嗪中间体的应用研究  

Study on the Application of Mannich Reaction to Synthesize the Intermediates of Clothianidin and Thiamethoxam

作　　者：魏义兰 常晓龙 周国娥[1] Wei Yi-lan;Chang Xiao-long;Zhou Guo-e(Hunan Chemical Vocational Technology College,College of Chemical Engineering,Zhuzhou Hunan 412000,China;Xinjiang Chemical Design Research Institute,Wulumuqi Xinjiang 830006,China)

机构地区：[1]湖南化工职业技术学院化学工程学院,湖南株洲412000 [2]新疆化工设计研究院有限责任公司,新疆乌鲁木齐830006

出　　处：《江西化工》2023年第4期21-24,共4页Jiangxi Chemical Industry

基　　金：湖南省教学厅科学研究项目(19C0643)。

摘　　要：为提高第2代新烟碱类杀虫剂噻虫胺与噻虫嗪的产品纯度,降低其在工业生产中的废水排放量,对噻虫胺中间体1,5-二甲基-2-硝基亚胺基-全氢-1,3,5-三嗪和噻虫嗪中间体3-甲基-4-硝基亚胺四氢-1,3,5-噁二嗪的反应机理进行研究。发现噻虫胺中间体1,5-二甲基-2-硝基亚胺基-全氢-1,3,5-三嗪的合成在碱性条件下进行,而噻虫嗪中间体3-甲基-4-硝基亚胺四氢-1,3,5-噁二嗪的合成既可在酸性也可在碱性条件下进行,酸性条件下产品收率更高,且都符合Mannich反应机理。Mannich反应在有机化学合成,特别是在药物合成方面具有非常重要的地位,展望了其在农药合成领域的发展趋势。In order to improve the purity of the products of the second generation of new nicotinic insecticides,clothianidin and thiamethoxam,and reduce their wastewater discharge in industrial production.The reaction mechanism of 3-methyl-4-nitroimino-tetrahydro-1,3,5-oxadiazine,the intermediate of thiamethoxam,and 1,5-dimethyl-2-nitroiminoperhydro-1,3,5-triazine,the intermediate of thiamethoxam,was studied.It was found that the synthesis of clothianidin intermediate 1,5-dimethyl-2-nitroimino-allhydro-1,3,5-triazine was carried out under alkaline conditions,while the synthesis of thiamethoxam intermediate 3-methyl-4-nitroiminothetrahydro-1,3,5-oxadiazine could be carried out under both acidic and alkaline conditions,and the product yield was higher under acidic conditions,and both conformed to the Mannich reaction mechanism.Mannich reaction plays a very important role in organic chemical synthesis,especially in drug synthesis.Its development trend in the field of pesticide synthesis is prospected.

关 键 词：3-甲基-4-硝基亚胺四氢-1 3 5-噁二嗪 1 5-二甲基-2-硝基亚胺基-全氢-1 3 5-三嗪 曼尼希反应 反应机理 

分 类 号：TQ453.2[化学工程—农药化工]