含1,3,4-噁二唑片段的胡椒碱类衍生物合成及杀螨活性  

Synthesis and acaricidal activity of piperine derivatives containing the 1,3,4-oxadiazole fragment

作　　者：李绍晨 王燕燕 方珊珊 王振 徐晖 吕敏 LI Shaochen;WANG Yanyan;FANG Shanshan;WANG Zhen;XU Hui;LYU Min(College of Plant Protection,Northwest A&F University,Yangling 712100,Shaanxi Province,China)

机构地区：[1]西北农林科技大学植物保护学院,陕西杨凌712100

出　　处：《农药学学报》2023年第5期1057-1067,共11页Chinese Journal of Pesticide Science

基　　金：国家自然科学基金(31872013).

摘　　要：为了开发基于天然产物的新型杀螨剂,以胡椒碱为先导化合物,设计并合成了26个含1,3,4-噁二唑杂环的胡椒碱类衍生物8a~8z,并经核磁共振氢谱(或碳谱)、红外光谱和高分辨质谱确证其结构。化合物8g通过X-射线单晶衍射确定其空间构型。采用玻片浸渍法测定了系列化合物对朱砂叶螨Tetranychus cinnabarinus Boisduval雌成螨的触杀活性。结果表明:化合物8m(LC_(50):0.41 mg/mL)、8r(LC_(50):0.36 mg/mL)及8u(LC_(50):0.32 mg/mL)表现出良好的杀螨活性,其活性分别为胡椒碱(LC_(50):15.64 mg/mL)的38.1、43.4及48.9倍,且化合物8u在0.3 mg/mL质量浓度下对朱砂叶螨有较好的室内防治效果,施药后第5天的防治效果为61.8%。构效关系分析发现:在胡椒碱C2位引入1,3,4-噁二唑杂环有利于提高其杀螨活性,且杀螨活性与噁二唑苯环上的取代基密切相关。To discovery novel acaricides based on natural products,twenty-six piperine derivatives containing 1,3,4-oxadiazoles(8a-8z)were designed and synthesized using piperine as a lead compound.Their structures were well characterized by 1H NMR(13C NMR),IR and HRMS.The steric configuration of compound 8g was confirmed by single crystal X-ray diffraction analysis.Their acaricidal activities were tested against female adults of Tetranychus cinnabarinus Boisduval by slide-dipping method.Compounds 8m(LC_(50):0.41 mg/mL),8r(LC_(50):0.36 mg/mL)and 8u(LC_(50):0.32 mg/mL)showed potent acaricidal activities which were 38.1,43.4 and 48.9 folds of that of its precursor piperine(LC_(50):15.64 mg/mL).Moreover,compound 8u also showed good control effects on T.cinnabarinus in the greenhouse,and its control efficiency was 61.8%on the 5th day after treatment at 0.3 mg/mL.The SARs analysis showed that introduction of 1,3,4-oxadiazoles on the C2 position of piperine was beneficial to the acaricidal activity,and the acaricidal activity was also related with the substituents on the phenyl of 1,3,4-oxadiazoles.

关 键 词：1 3 4-噁二唑 胡椒碱 天然产物 杀螨活性 朱砂叶螨 构效关系 

分 类 号：O626.24[理学—有机化学] TQ454.2[理学—化学]