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有机化学
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有机化学 ›› 2008, Vol. 28 ›› Issue (04): 617-621. 上一篇    下一篇

研究论文

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

康铁牛a，凌云a，芮昌辉b，杨新玲*,a，范贤林b，陈馥衡a   

  1. (a中国农业大学理学院应用化学系 北京 100094)
    (b中国农业科学院植物保护研究所 北京 100094)
  • 收稿日期:2007-04-18 修回日期:2007-08-24 发布日期:2008-04-17
  • 通讯作者: 杨新玲

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

KANG Tie-Niua,LING Yuna,RUI Chang-Huib,YANG Xin-Ling*,a
FAN Xian-Linb,CHEN Fu-Henga   

  1. (a Department of Applied Chemistry, China Agricultural University, Beijing 100094)
    (b Institute of Plant Protection, Chinese Academy of Agricultural Sciences, Beijing 100094)
  • Received:2007-04-18 Revised:2007-08-24 Published:2008-04-17
  • Contact: YANG Xin-Ling

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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1H NMR, 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(1000 μg/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62.5 μg/mL)下对蚜虫的生物活性反而高于对照药剂.

关键词: 五元杂环, EBF类似物, 合成, 生物活性

In order to find novel leading compounds used to control aphids, eight E-β-farnesene (EBF) analogues were synthesized from the skeletal structure of EBF, the main component of aphid alarm phero-mones, where the conjugate double bond was superseded by nitrogen heterocyclic compounds such as N-nitroimidazolidin-2-imine, thiazolidine-2-thione, oxazolidin-2-one, etc.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 1000 µg/mL.

Key words: EBF analogue, azaheterocycle, synthesis, biological activity