3D-QSAR-Based Molecular Design to Discover Ultrahigh Active N-Phenylpyrazoles as Insecticide Candidates

粘虫 菜蛾 小菜蛾 效力 数量结构-活动关系 化学 立体化学 兰尼定受体 行动方式 受体 生物 幼虫 生物化学 体外 植物
作者
Jinzhou Ren,Xia Ji,Gao Wei,Zhenwu Yu,Kun Li,Lixia Xiong,Na Yang,Yuxin Li,Zhengming Li,Zhijin Fan
出处
期刊:Journal of Agricultural and Food Chemistry [American Chemical Society]
卷期号:71 (10): 4258-4271 被引量:8
标识
DOI:10.1021/acs.jafc.2c08719
摘要

Three-dimensional quantitative structure-activity relationship (3D-QSAR) is one of the most important and effective tools to direct molecular design in new pesticide development. Chlorantraniliprole is an anthranilic diamide ryanodine receptor (RyR) agonist with ultrahigh activity, high selectivity, and mammalian safety. To continue our studies on new insecticide development, here, we designed new insecticidal N-phenylpyrazoles by using 3D-QSAR of chlorantraniliprole analogues as a guide. Most of the target compounds synthesized exhibited medium to excellent activity against Mythimna separata, Plutella xylostella, and Spodoptera frugiperda. Compounds III b and III y showed similar activity against M. separata as chlorantraniliprole (LC50 values: 0.21, 0.25, and 0.16 μg mL-1 respectively). Compounds III b exhibited a 3-fold higher potency against P. xylostella than chlorantraniliprole. For S. frugiperda, the potency of III a and III b was 2.9 and 2.0 times higher than that of the positive control, respectively. The mode of action of the title compounds was validated by calcium imaging experiments and molecular docking using their target RyRs. III b can dock well with mutated P. xylostella RyRs, implying a potentially lower cross-resistance risk as compared with commercial RyR agonists. Density functional theory calculations suggested the feasibility of higher potency with the structural modifications. Compound III b was found to be an ultrahigh active insecticidal candidate with a broad spectrum for integrated pest management.
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