脱氢枞基1,2,4-三唑席夫碱类衍生物的合成及杀虫活性研究  

Synthesis and Insecticidal Activity of Dehydroabietyl-1,2,4-triazole Schiff Base Derivatives

作　　者：徐仁乐 韩旭 常美悦 谷世豪 李健[1] XU Renle;HAN Xu;CHANG Meiyue;GU Shihao;LI Jian(College of Forestry,Northwest A&F University,Yangling 712100,China)

机构地区：[1]西北农林科技大学林学院,陕西杨陵712100

出　　处：《林产化学与工业》2024年第6期129-139,共11页Chemistry and Industry of Forest Products

基　　金：国家自然科学基金资助项目(32371815)。

摘　　要：基于脱氢枞酸羧基改性,设计合成2个系列脱氢枞基1,2,4-三唑席夫碱类衍生物,所有目标化合物均经过红外光谱(FT-IR)、核磁共振氢谱(1 H NMR)、核磁共振碳谱(^(13)C NMR)和高分辨质谱验证。采用“浸虫法”和“叶片浸渍法”分别评估该类化合物对孑孓和玉米黏虫的杀灭活性,结果表明:改性修饰后的脱氢枞基1,2,4-三唑衍生物具有较好的杀孑孓效果。其中化合物3g、3i、3j、4b和4c在48 h内对孑孓具有较好的杀灭效果(校正死亡率均超过90%),与阳性对照呋虫胺基本相当(96.67%)。通过量子化学计算对目标化合物的活性部位进行分析,结果表明:杀虫活性与目标化合物的最低未占据轨道(LUMO)和分子静电势(ESP)之间存在一定的关系,含吸电子基团(F、Cl和Br)的化合物表现出更好的杀虫活性。Two Series dehydroabietyl-1,2,4-triazole Schiff base derivatives were designed and synthesized based on the modification of the carboxyl group of dehydroabietic acid.All target compounds were verified by FT-IR,1 H NMR,^(13)C NMR and LC-MS.The insecticidal activities of these compounds against Culex asiatica and Mythimna separate were evaluated through insect soaking method and leaf soaking method,respectively.The results showed that the modified dehydroabietyl-1,2,4-triazole derivatives had good insecticidal effects.Among them,compounds 3g,3i,3j,4b and 4c had a relatively good killing effect on C.asiatica within 48 hours(the corrected mortality rate all exceeded 90%),which was basically equivalent to the positive control dinotefuran(96.67%).The analysis of the active site of the target compounds by quantum chemical calculations showed that there was a certain relationship between insecticidal activity and the lowest unoccupied molecular orbital(LUMO)and molecular electrostatic potential(ESP)of the target compound.Particularly,the compounds containing electron withdrawing groups(F,Cl,and Br)exhibited better insecticidal activity.

关 键 词：脱氢枞酸 1 2 4-三唑 杀虫活性 

分 类 号：TQ35[化学工程] O626[理学—有机化学]