State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Guiyang, China.
College of Chemistry and Chemical Engineering, Anshun University, Anshun, China.
Pest Manag Sci. 2022 Nov;78(11):4983-4993. doi: 10.1002/ps.7121. Epub 2022 Aug 29.
In our previous work, we applied a new synthetic strategy to design and synthesize a series of imidazopyridine mesoionic derivatives with an ester group. The newly synthesized compounds had excellent insecticidal activity against aphids; however, insecticidal activity against planthoppers was less than satisfactory. In the present study, we designed and synthesized a series of novel imidazopyridine mesoionic compounds, containing an amido group, and these compounds were found to have improved insecticidal activity against planthoppers.
The bioassay results demonstrated that most of the target compounds had moderate-to-good insecticidal activity against Sogatella furcifera, and some exhibited good-to-excellent insecticidal activity against Aphis craccivora. Among them, compound C6 had the highest insecticidal activity against S. furcifera and A. craccivora, with LC values of 10.5 and 2.09 μg mL , respectively. Proteomic results suggested that the differentially expressed proteins mainly were enriched in the nervous system-related pathways after compound C6 treatment. Enzymatic assay results showed that compound C6 and triflumezopyrim had a certain inhibitory effect on acetylcholinesterase. Molecular docking and real-time quantitative PCR results indicated that compound C6 not only may act on the nicotinic acetylcholine receptor, but also may interact with the α4 and β1 subunits of this receptor.
The results reported here contribute to the development of new mesoionic insecticides and further our understanding of the mode-of-action of imidazopyridine mesoionic derivatives. © 2022 Society of Chemical Industry.
在我们之前的工作中，我们应用了一种新的合成策略来设计和合成一系列含有酯基的咪唑并吡啶杂环化合物。新合成的化合物对蚜虫具有优异的杀虫活性，但对飞虱的杀虫活性不尽如人意。在本研究中，我们设计并合成了一系列新型的含有酰胺基的咪唑并吡啶杂环化合物，发现它们对飞虱具有改善的杀虫活性。
生物测定结果表明，大多数目标化合物对褐飞虱具有中等至良好的杀虫活性，有些对桃蚜具有良好至优异的杀虫活性。其中，化合物 C6 对褐飞虱和桃蚜的杀虫活性最高，LC 值分别为 10.5 和 2.09μg/mL。蛋白质组学结果表明，化合物 C6 处理后差异表达的蛋白质主要富集在神经系统相关途径中。酶活性测定结果表明，化合物 C6 和三氟咪啶磺隆对乙酰胆碱酯酶具有一定的抑制作用。分子对接和实时定量 PCR 结果表明，化合物 C6 不仅可能作用于烟碱型乙酰胆碱受体，还可能与该受体的α4 和β1 亚基相互作用。
本研究结果为新型杂环杀虫剂的开发提供了依据，并进一步了解了咪唑并吡啶杂环衍生物的作用模式。© 2022 英国化学学会。
