银锭夜蛾性信息素拮抗剂的合成及活性研究

Synthesis and Activity of Sex Pheromone Antagonist of Macdunnoughia crassisigna Warren

银锭夜蛾Macdunnoughia crassisigna Warren是豆类作物和十字花科蔬菜上重要的食叶性害虫。因其具有暴食性,迁飞性等特点,逐渐成为东北、华北地区重要的农业害虫。由于缺乏有效的绿色防控技术,目前化学农药仍是防控银锭夜蛾有效的方法之一。为提高银锭夜蛾的防治效果,以银锭夜蛾性信息素主要成分顺−7−十二碳烯乙酸酯(Z7−12:Ac)、顺−9−十四碳烯乙酸酯(Z9−14:Ac)为母体结构,通过酯化反应得到结构新颖的类似物14个,结构经GC−MS、1 H NMR、13C NMR和HR−MS确证。触角电生理试验(EAG)表明,有11个类似物具有较好的EAG反应。EAG抑制试验发现,类似物4、13和14具有明显的抑制效果。在100μg剂量下,类似物4对Z7−12:Ac的抑制率达50.2%。风洞试验表明,当添加1500μg的类似物4时,对银锭夜蛾的干扰尤为显著,没有成虫到达诱芯。田间试验表明,类似物4具有潜在的抑制活性,当添加150、1500μg的类似物4时,平均诱捕量与性信息素存在显著性差异,抑制率分别为56.90%、59.34%。研究结果有助于揭示性信息素拮抗剂对银锭夜蛾种内化学通讯调控方式,为银锭夜蛾绿色防控技术提供新的思路与手段。

Macdunnoughia crassisigna Warren is an important leaf-eating lepidopteran insect pest on legume crops and cruciferous vegetables.Being voracious and migratory,M.crassisigna has become an important agricultural pest in the Northeast China and North China.Due to the lack of effective green management technology,chemical pesticides are still one of the effective methods to control M.crassisigna.In order to improve the control of M.crassisigna,fourteen novel sex pheromone analogues were designed and synthesized by esterification reaction,based on the structure of sex pheromone components(Z7-12:Ac and Z9-14:Ac).All compounds were confirmed by Gas Chromatography-Mass Spectrometry(GC-MS),nuclear magnetic resonance(NMR)and high-resolution mass spectrometry(HRMS).Direct EAG activity tests on the antennae of M.crassisigna revealed that 11 analogues elicited high EAG responses.The EAG inhibition tests found that sex pheromone analogs 4,13 and 14 had obvious inhibitory effects.At a dose of 100μg,the inhibition rate of analog 4 on Z7-12:Ac reached 50.2%.The wind tunnel test results showed that when analog 4 was added at 1500μg,no males reached the wind tunnel lures.Field test results indicated that analog 4 showed strong inhibitory activity when added at different doses.When analog 4 was added at 150μg or 1500μg,the average trapping catches were significantly lower than SP,resulting in inhibition rates of 56.9%and 59.3%,respectively.The results are helpful to reveal the regulation of sex pheromone antagonists on the intra-species chemical communication of M.crassisigna,and provide new ideas and means for green management of M.crassisigna.