Chinese Journal of Organic Chemistry >
Design, Synthesis and Repellent Activity of (E)-β-Farnesene Analogues Containing Benzene Ring with Different Substitutions
Received date: 2016-03-14
Revised date: 2016-04-07
Online 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.
Zhang Jingpeng , Qin Yaoguo , Li Wenhao , Ling Yun , Yang Libo , Song Dunlun , Yang Xinling . Design, Synthesis and Repellent Activity of (E)-β-Farnesene Analogues Containing Benzene Ring with Different Substitutions[J]. Chinese Journal of Organic Chemistry, 2016 , 36(8) : 1883 -1889 . DOI: 10.6023/cjoc201603021
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