新型含氮五元杂环E-β-法尼烯类似物的合成及生物活性研究

Synthesis of E-β-Farnesene Analogues Containing Five-Membered Azaheterocycles and Their Biological Activity

为了寻求新型蚜虫防治先导化合物,以蚜虫报警信息素的主要成分E-β-法尼烯(E-β-farnesene,简称EBF)的骨架结构为母体,分别用N-氰基-亚胺基-1,3-噻唑烷、2-噻唑硫酮、2-羰基-1,3-噁唑烷、1-取代-2-硝基亚胺基-1,3-咪唑烷等含氮五元杂环取代EBF中的共轭双键,设计合成了8个未见文献报道的EBF类似物,其结构均经1HNMR,IR和元素分析确证,并分析比较了不同类型杂环的化学反应和生物活性差异.初步生物活性试验结果表明,目标化合物对蚜虫具有一定的生物活性,其中4e在5个测试浓度下的活性均优于对照药剂;有意思的现象是,一些在高浓度(1000μg/mL)下活性低于对照药剂噻虫啉的目标物(如4a～4c,4f～4h),在低浓度(如62.5μg/mL)下对蚜虫的生物活性反而高于对照药剂.

In order to find novel leading compounds used to control aphids, eight E-fl-farnesene （EBF） analogues were synthesized from the skeletal structure of EBF, the main component of aphid alarm pheromones, where the conjugate double bond was superseded by nitrogen heterocyclic compounds such as N-nitroimidazolidin-2-imine, thiazolidine-2-thione, oxazolidin-2-one, etc. The structures of all the target compounds were confirmed by ^1H NMR, IR spectra and elemental analysis, and the different reaction and biological activities of these compounds were also discussed. The results of biological tests indicated that most compounds showed insecticidal activity against Lipaphis erysimi, especially the inhibition rate of 4e was higher than that of thiacloprid at testing five concentrations. The interesting phenomenon is that at a lower concentration （e.g. 62.5 μg/mL）, the inhibition rate of most compounds is better than that of thiacloprid despite that they are worse than thiacloprid at 1000μg/mL.