新型银锭夜蛾性信息素类似物的合成及初步活性

Synthesis and Preliminary Activities of Novel Sex Pheromone Analogs of Macdunnoughia crassisigna Warren

昆虫性信息素具有微量、高效、绿色等优点,利用性信息素防治害虫具有良好的应用前景。但随着对性信息素的研究不断深入,性信息素田间释放速率较快、易分解等问题日益凸显。为提高性信息素对银锭夜蛾的防治效果,以银锭夜蛾性信息素主要成分顺-7-十二碳烯乙酸酯(Z7-12:Ac)为母体结构,通过醇与酰氯或酸酐的反应,合成结构稳定且新颖的6种性信息素类似物,包括顺-7-十二碳烯-2,2-二氟代乙酸酯(Y1),顺-7-十二碳烯-2,2,2-三氟乙酸酯(Y2),顺-7-十二碳烯-2,2,3,3,3-五氟丙酸酯(Y3),顺-7-十二碳烯-2,2,2-三氟甲磺酸酯(Y4),顺-7-十二碳烯-2-溴丙酸酯(Y5),顺-7-十二碳烯-3-甲硫基丙酸酯(Y6),其结构经核磁共振(NMR)和高分辨质谱(HR-MS)表征。室内生物活性研究表明:所有的性信息素类似物在触角电生理试验(EAG)中均表现出一定的生物活性,其中Y1具有较好的剂量-效应关系,在浓度10μg时EAG直接刺激响应值为2.07 mV。

Sex pheromones have the advantage of microscale,high efficiency,green,and the use of insect sex pheromones to control pests have a good application prospect.However,with the deepening of research on sex pheromones,the problem of rapid release rate and easy decomposition of sex pheromone in the field has become increasingly prominent.In order to improve the control effect of sex pheromone on Macdunnoughia crassisigna Warren,six novel and stable pheromone analogues were synthesized by the reaction of alcohol with acyl chloride or anhydride,used cis-7-dodecene acetate(Z7-12:Ac),the main component of the sex pheromone of Macdunnoughia crassisigna Warren,as the parent structure,including cis-7-dodecen-1-yl-2,2-difluoroacetate(Y1),cis-7-dodecen-1-yl-2,2,2-trifluoroacetate(Y2),cis-7-dodecen-1-yl-2,2,3,3,3-pentafluoropropanoate(Y3),cis-7-dodecen-1-yl-trifluoromethanesulfonate(Y4),cis-7-dodecen-1-yl-2-bromopropanoate(Y5),cis-7-dodecen-1-yl-3-(methylthio)propanoate(Y6).The structures are characterized by NMR and HR-MS.Laboratory bioactivity studies have shown that all sex pheromone analogs exhibit some biological activities in the electrophysiological test(EAG).Among them,the analog Y1 has a good dose-effect relationship,and the direct stimulation response value of EAG is 2.07 mV at a concentration of 10μg.This research will help to screen and trap the better pheromone analogs of Macdunnoughia crassisigna Warren,and provide new ideas for the green control of Macdunnoughia crassisigna Warren.