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.
作者
徐仁乐
韩旭
常美悦
谷世豪
李健
XU Renle;HAN Xu;CHANG Meiyue;GU Shihao;LI Jian(College of Forestry,Northwest A&F University,Yangling 712100,China)
出处
《林产化学与工业》
CAS
CSCD
北大核心
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)。
关键词
脱氢枞酸
1
2
4-三唑
杀虫活性
dehydroabietic acid
1,2,4-triazole
insecticidal activity
