Citation: 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 shu

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

Zhang Jingpeng ^a ,
Qin Yaoguo ^a ,
Li Wenhao ^a ,
Ling Yun ^a ,
Yang Libo ^b ,
Song Dunlun ^b ,
Yang Xinling ^a,*,,

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

Corresponding author: Yang Xinling, yangxl@cau.edu.cn
Received Date: 14 March 2016
Revised Date: 7 April 2016

Fund Project: Project supported by the National Natural Science Foundation of China No. 21132003

Figures(2)

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.
- EBF analogues,
- benzene ring,
- N-alkylation,
- repellent activity,
- structure-activity relationship
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