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为了发现驱避蚜虫的新型高活性化合物,以蚜虫报警信息素(E)-β-farnesene(EBF)为先导,引入不同取代的苯环替代EBF结构中不稳定的共轭双键,设计了一系列含苯环的EBF类似物.优化了一条苯胺和香叶基氯反应的N-烷基化路线,在最优条件下以39%~83%的收率合成了19个目标化合物,所有化合物结构均通过1H NMR、13C NMR及HRMS确证.生物活性测试结果表明,部分化合物对桃蚜具有一定驱避活性,其中4d、4h和4k驱避率分别高达56.3%、58.3%和50.3%.目标化合物构效关系显示4-位卤素取代化合物活性较高.
In order to find out a new type of highly active compound that repels aphids, we introduce a different substituted benzene ring instead of the unstable conjugate double bond in the structure of EBF by aphid alarm pheromone (E) -β-farnesene (EBF) Series of EBF analogs containing benzene rings. An N-alkylation route of aniline and geranyl chloride was optimized. Twenty-nine target compounds were synthesized in yields of 39% -83% under optimum conditions. All the compounds The results of bioassay showed that some of the compounds had certain repellent activity against Myzus persicae and the repellents of 4d, 4h and 4k were 56.3%, 58.3% and 50.3%, respectively.The target compounds The structure-activity relationship shows that 4-position halogen substituted compounds are more active.