新型含N-COCF_(3)硫亚胺取代的手性双酰胺类化合物的合成与生物活性研究  

Synthesis and Insecticidal Activities of Novel Optically Active Dicarboxamides Containing N-Trifluoroacetyl Sulfulimiyl Substituents

作　　者：周莎[1] 王目阔 谢伟彬 周沙 熊丽霞[1] 赵毓[1] 李正名[1] Zhou Sha;Wang Mukuo;Xie Weibin;Zhou Shaa;Xiong Lixia;Zhao Yu;Li Zhengming(National Pesticidal Engineering Centre(Tianjin),State Key Laboratory of Elemento-organic Chemistry,College of Chemistry,Nankai University,Tianjin 300071;State Key Laboratory of Medicinal Chemical Biology,Tianjin Key Laboratory of Molecular Drug Research,College of Pharmacy,Nankai University,Tianjin 300353)

机构地区：[1]南开大学化学学院元素有机化学国家重点实验室农药国家工程中心(天津),天津300071 [2]南开大学药学院药物化学生物学重点实验室天津市药物分子研究重点实验室,天津300353

出　　处：《有机化学》2021年第9期3532-3538,共7页Chinese Journal of Organic Chemistry

基　　金：国家重点研发计划(No.2018YFD0200100);国家自然科学基金(No.21602118)资助项目.

摘　　要：邻苯二甲酰胺类化合物是一类作用于鱼尼丁受体的特殊杀虫剂,它具有高效、低毒、作用机制独特、对环境友好、对哺乳动物十分安全等优异的特点.为了探索新颖的结构,设计合成了一系列碳硫双手性N-COCF_(3)硫亚胺类化合物,并通过熔点、^(1)H NMR、高分辨率质谱(HRMS)和比旋光度进行了化合物表征.同时也探索了这些结构对东方粘虫的活性并总结了其构效关系.初步的生测结果表明,某些化合物对东方粘虫显示出良好的杀虫活性.这些异构体的杀虫活性顺序为(S_(c),R_(s))≥(S_(c),S_(s)).值得一提的是,在苯胺部分中含有2-CH_(3)-4-Cl的化合物比具有3-CF_(3)的化合物具有更好的生物活性.该研究为进一步研究含有硫亚胺结构的邻苯二甲酰胺类化合物提供了重要信息.Dicarboxamide is a class of special insecticide targeting at Ryanodine Receptor(RyR)with potent activity,new mode of action and eco-friendly characteristics in modern pest control.To explore new structures acting on RyR,a series of new dual chiral N-COCF_(3) sulfiliminyl derivatives were designed,synthesized,and characterized by melting point,^(1)H NMR,high-resolution mass spectrometry(HRMS)and optical polarimeter.Their insecticidal activity against oriental armyworm(Pseudaletia separata Walker)were evaluated and the structure-activity relationship were summarized.The bioactivity revealed that some compounds showed favourable insecticidal activities against oriental armyworm.The sequence of these isomers’insecticidal activity was(S_(c),R_(s))≥(S_(c),S_(s)).It was worth noting that compounds containing 2-CH_(3)-4-Cl in the anilide moiety gave better activity than the compounds with 3-CF_(3).The study provided some important information for the further research of sulfiliminyl dicarboxamides.

关 键 词：手性 硫亚胺 生物活性 鱼尼丁受体 邻苯二甲酰胺类 

分 类 号：TQ453.2[化学工程—农药化工]