Citation: Zhang Jingpeng, Yang Zhaokai, Qin Yaoguo, Yang Xinling. Design, Synthesis and Biological Activity of (E)-β-Farnesene Analogues Containing 1, 2, 3-Thiadiazole[J]. Chinese Journal of Organic Chemistry, ;2020, 40(9): 2971-2979. doi: 10.6023/cjoc202005075 shu

Design, Synthesis and Biological Activity of (E)-β-Farnesene Analogues Containing 1, 2, 3-Thiadiazole

a.
Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193
b.
Research Institute of Wood Industry, Chinese Academy of Forestry, Beijing 100091

Corresponding author: Yang Xinling, yangxl@cau.edu.cn
Received Date: 28 May 2020
Revised Date: 12 June 2020
Available Online: 30 June 2020
Fund Project: the National Key Research and Development Plan 2017YFD0200504Project supported by the National Key Research and Development Plan (No. 2017YFD0200504)

Figures(5)

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 15 EBF analogues were designed and synthesized by replacing unstable conjugated double bond of EBF with 1, 2, 3-thiadiazole. Their structures were confirmed by ¹H NMR, ¹³C NMR, IR and HRMS analysis. Repellent activity results indicated that analogues displayed better repellent activity against Myzus persicae (Sulzer). Among which compounds N-((E)-3, 7-dimethyl-2, 6-octadien-1-yl)-N-(2-naphthyl)-4-methyl-1, 2, 3-thiadiazole-5-carboxamide (8d), N-((E)-3, 7-dimethyl-2, 6-octadien-1-yl)-N-(4-methyl-pyridine-2-yl)-4-methyl-1, 2, 3-thiadiazole-5-carboxamide (8l) and N-((E)-3, 7-dimethyl-2, 6-octadien-1-yl)-N-(5-methyl-pyridine-2-yl)-4-methyl-1, 2, 3-thiadiazole-5-carboxamide (8m) exhibited excellent repellent activity of 63.1%, 61.3% and 63.4% respectively. The aphicidal bioassay results showed that most analogues exhibited considerable aphicidal activity against Myzus persicae. Especially, analogues N-((E)-3, 7-dimethyl-2, 6-octadien-1-yl)-N-(4-CN-phenyl)-4-methyl-1, 2, 3-thiadiazole-5-carboxamide (8b), N-((E)-3, 7-dimethyl-2, 6-octadien-1-yl)-N-(6-methyl-pyridine-2-yl)-4-methyl-1, 2, 3-thiadiazole-5-carboxamide (8g), N-((E)-3, 7-dimethyl-2, 6-octadien-1-yl)-N-(2-pyridyl)-4-methyl-1, 2, 3-thiadiazole-5-carboxamide (8j), N-((E)-3, 7-dimethyl-2, 6-octadien-1-yl)-N-(3-methyl-pyridine-2-yl)-4-methyl-1, 2, 3-thiadiazole-5-carboxamide (8k), 8l, 8m and N-((E)-3, 7-dimethyl-2, 6-octadien-1-yl)-N-(5-methyl-1, 3, 4-thiadiazole-2-yl)-4-methyl-1, 2, 3-thiadiazole-5-carboxamide (8o) exhibited high activity with LC₅₀ values of 10.2, 9.0, 25.1, 31.7, 8.4, 12.8 and 9.6 μg/mL, respectively, which were higher than the lead compound (E)-β-farnesene, but lower than commercial insecticide pymetrozine with LC₅₀ of 7.1 μg/mL.
- 1, 2, 3-thiadiazole,
- EBF analogues,
- synthesis,
- repellent activity,
- insecticidal activity
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