Citation: Zhang Jingpeng, Qin Yaoguo, Li Xinlu, Song Dunlun, Liu Junjie, Yang Xinling. Design, Synthesis and Biological Activity of (E)-β-Farnesene Analogues Containing Imidogen[J]. Chinese Journal of Organic Chemistry, ;2017, 37(4): 987-995. doi: 10.6023/cjoc201611028 shu

Design, Synthesis and Biological Activity of (E)-β-Farnesene Analogues Containing Imidogen

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: 22 November 2016
Revised Date: 18 December 2016

Fund Project: the National Natural Science Foundation of China 21132003

Figures(4)

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 EBF analogues containing imidogen were designed by replacing unstable conjugated double bonds of EBF with different aromatic ring. Nineteen EBF analogues were synthesized via two reaction routes of N-alkylation and reductive amination. Their structures were confirmed by ¹H NMR, ¹³C NMR, IR and HRMS analysis. The bioassay and structure-activity relationship analysis were carried out. The result indicated that title compounds containing benzene or pyridine displayed obvious repellent activity against Myzus persicae (Sulzer). Especially, compounds 3g, 3l and 3m exhibited excellent repellent activity of 62.0%, 62.5% and 64.6% respectively. Moreover, the title compounds containing 1, 3, 4-thiadiazole ring showed certain insecticidal activity against M. persicae. In particular, the mortality rate of compounds 3i, 3l, 3r and 3s were 70.7%, 72.6%, 70.4% and 75.5% at a concentration of 200 μg/mL, which were higher than the lead EBF. However, compound 3a, in which the conjugated double bonds were replaced with butyl, showed obviously neither repellent nor aphicidal activity.
- EBF analogues,
- imidogen,
- synthesis,
- repellent activity,
- insecticidal activity,
- structure-activity relationship
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