Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (8): 1883-1889.DOI: 10.6023/cjoc201603021 Previous Articles     Next Articles



张景朋a, 秦耀果a, 李文浩a, 凌云a, 杨立波b, 宋敦伦b, 杨新玲a   

  1. a 中国农业大学理学院应用化学系 北京 100193;
    b 中国农业大学植物保护学院昆虫学系 北京 100193
  • 收稿日期:2016-03-14 修回日期:2016-04-07 发布日期:2016-04-20
  • 通讯作者: 杨新玲
  • 基金资助:

    国家重点自然科学基金(No. 21132003)资助项目.

Design, Synthesis and Repellent Activity of (E)-β-Farnesene Analogues Containing Benzene Ring with Different Substitutions

Zhang Jingpenga, Qin Yaoguoa, Li Wenhaoa, Ling Yuna, Yang Libob, Song Dunlunb, Yang Xinlinga   

  1. a Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193;
    b Department of Entomology, College of Plant Protection, China Agricultural University, Beijing 100193
  • Received:2016-03-14 Revised:2016-04-07 Published:2016-04-20
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21132003).

In order to discover novel compounds with high-activity to control aphid, aphid alarm pheromone (E)-β-farnesene (EBF) was chosen as lead compound and a series of substituted EBF analogues were designed by replacing unstable conjugated double bond of EBF with different substitutions benzene ring. An N-alkylation route was optimized by using aniline and (E)-1-chloro-3,7-dimethyl-2,6-octadiene. Nineteen EBF analogues were synthesized with yields of 39%~83% in this optimization reaction condition. Their structures were confirmed by 1H NMR, 13C NMR and HRMS analysis. Bioassay showed that the title compounds demonstrated repellent activity against Myzus persicae (Sulzer). In particular, 4d, 4h and 4k exhibited excellent repellent activity of 56.3%, 58.3% and 50.3% respectively. The performed structure-activity relationship indicated that introduction of halogen group at the 4 position of phenyl ring displayed relatively higher activity.

Key words: EBF analogues, benzene ring, N-alkylation, repellent activity, structure-activity relationship