文献类型： 外文期刊

第一作者： Liu Min

作者： Liu Min;Xiao Yumei;Zhao Fenghai;Qin Zhaohai;Yang Dongyan;Su Wangcang

作者机构：

关键词： bioisosterism; 5-nitroimine-1,2,4 triazoline; insecticidal activity; fungicidal activity; molecular docking

期刊名称：CHINESE JOURNAL OF ORGANIC CHEMISTRY （ 影响因子：1.9； 五年影响因子：1.3 ）

ISSN： 0253-2786

年卷期： 2023 年 43 卷 8 期

页码：

收录情况： SCI

摘要： Olefin-imidacloprid is a highly active metabolite of imidacloprid. To solve the problem of high bee toxicity of olefin-imidacloprid, according to the bioisosterism, a series of novel olefin-imidacloprid mimics containing 1,3-disubstituted1,2,4-triazoline were designed and synthesized. The insecticidal activity of these compounds against A. craccivora, Nilaparvata lugens and F. occidentalis and in vitro antifungal activity were determined. The results showed that these compounds showed certain insecticidal activity at 400 mu g/mL and 100% lethal rate was obtained from compound II-7 at 100 mu g/mL against F. occidentalis. The toxicity of some compounds to bees was predicted by admetSAR, and they showed low level of toxicity. On the other hand, the target compounds showed different degrees of antifungal activity against 9 plant pathogenic fungi at the concentration of 50 mu g/mL. Compound I-15 exhibited the highest activity with the inhibition rate higher or equal to hymexazol against five pathogens. The structure-activity relationship analysis showed that the compounds bearing alkyl substituent at site 3 in triazoline unit displayed higher insecticidal activity than that of an aryl substitution, meanwhile, the more lipophilic groups, the higher fungicidal activity. The substitution of pyridine ring or thiazole ring at site 1 in triazoline unit had little effect on their antifungal activity. The molecular docking results showed that the binding pattern of compound II-7 to acetylcholine binding protein (AChBP) was similar to that of imidacloprid (IMI), indicating that these compounds also had the potential to bind to AChBP, which provided a new reference for further molecular optimization.

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