Department of Applied Chemistry, College of Science, China Agricultural University, Key Laboratory of Pesticide Chemistry and Application, Ministry of Agriculture, Beijing 100193, People's Republic of China.
J Agric Food Chem. 2011 Mar 23;59(6):2456-61. doi: 10.1021/jf104712c. Epub 2011 Feb 22.
(E)-β-farnesene is a strong and efficient alarm pheromone in most aphid species. However, applications in agriculture are prevented by its relatively high volatility, its susceptibility to oxidation and its complex and expensive synthesis. To develop novel compounds for aphid control, we have designed and synthesized analogues of (E)-β-farnesene, containing a pyrazole moiety present in several insecticides. Their structures have been confirmed by 1H NMR, elemental analysis, high-resolution mass spectroscopy and IR. Binding activities to three odorant-binding proteins (OBPs) of the pea aphid Acythosiphon pisum have been evaluated and correlated with their structures with reference to (E)-β-farnesene. Several derivatives were shown both to bind to A. pisum OBPs with a specificity similar to that of (E)-β-farnesene and to have aphicidal activity comparable to that of thiacloprid, a commercial insecticide. The compounds synthesized in this work represent new potential agents for aphid population control and provide guidelines to design analogues of (E)-β-farnesene endowed with both insecticidal and repellent activity for aphids.
(E)-β-法呢烯是大多数蚜虫物种的强烈有效的报警信息素。然而，由于其相对较高的挥发性、易氧化性以及复杂和昂贵的合成，其在农业中的应用受到了限制。为了开发新型的蚜虫控制化合物，我们设计并合成了(E)-β-法呢烯的类似物，其中包含几种杀虫剂中存在的吡唑部分。它们的结构通过 1H NMR、元素分析、高分辨率质谱和 IR 得到了确认。评估了它们与豌豆蚜 Acythosiphon pisum 的三种气味结合蛋白（OBP）的结合活性，并参考(E)-β-法呢烯对其结构进行了相关性分析。结果表明，几种衍生物均与 A. pisum OBP 具有相似的结合特异性，并且具有与噻虫啉相当的杀虫活性，噻虫啉是一种商业杀虫剂。本工作中合成的化合物代表了新的潜在的蚜虫种群控制剂，并为设计具有杀虫和驱避活性的(E)-β-法呢烯类似物提供了指导。
