Chin. J. Org. Chem. ›› 2008, Vol. 28 ›› Issue (04): 617-621. Previous Articles     Next Articles

Original Articles

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

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from the skeletal structure of EBF, the main component of aphid alarm phero-mones, where the conjugate double bond was superseded by nitrogen heterocyclic compounds such as N-nitroimidazolidin-2-imine, thiazolidine-2-thione, oxazolidin-2-one, etc.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