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为了发现控制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,引入不同类型的芳香环(叔丁基)替代EBF结构中不稳定的共轭双键,设计了一系列含亚胺基EBF类似物.采用N-烷基化反应和还原胺化反应两种路线合成了19个目标化合物.所有化合物结构均通过~1HNMR、~(13)CNMR、IR及HRMS确证.对目标物进行了生物活性测试并探讨了结构活性关系,结果表明:含苯环或吡啶环的化合物对桃蚜具有较好的驱避活性,其中以3g、3l和3m最为显著,驱避率分别为62.0%、62.5%和64.6%;含1,3,4-噻二唑等杂环的化合物对桃蚜具有一定的杀虫活性,在200μg/m L浓度下化合物3i、3l、3r和3s的致死率分别为70.7%、72.6%、70.4%和75.5%,显著高于先导EBF;而含叔丁基的非环EBF类似物的驱避和杀蚜活性均不明显.
In order to find out a new type of highly active compound to control aphids, the aphid alarm pheromone (E) -β-farnesene (EBF) was used as a precursor to introduce different types of aromatic rings (tert-butyl) , A series of imine-based EBF analogues were designed and 19 target compounds were synthesized by N-alkylation and reductive amination reactions.All the structures were characterized by ~ 1H NMR, ~ (13) CNMR, IR And HRMS confirmation.The biological activity of the target was tested and the structure activity relationship was explored.The results showed that the compound containing benzene ring or pyridine ring had good repellent activity against Myzus persicae and the most significant was 3g, 3l and 3m , The repellent rates were 62.0%, 62.5% and 64.6%, respectively. The compounds containing 1,3,4-thiadiazole and other heterocycles had certain insecticidal activities against Myzus persicae. Under the concentration of 200μg / mL, the compounds 3i, The lethal rates of 3l, 3r and 3s were 70.7%, 72.6%, 70.4% and 75.5%, respectively, which were significantly higher than that of leading EBF. However, the repellent and aphid-killing activities of tert-butyl non-cyclic EBF analogues were not obvious.