含有单氟烯烃酰胺接头的邻氨基苯甲酸二酰胺作为潜在的昆虫 RyR 激活剂：设计、合成、生物评价和计算研究,Journal of Agricultural and Food Chemistry

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含有单氟烯烃酰胺接头的邻氨基苯甲酸二酰胺作为潜在的昆虫 RyR 激活剂：设计、合成、生物评价和计算研究
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2023-02-03 , DOI: 10.1021/acs.jafc.2c07680
Guantian Yang ₁ , Cong Zhou ₁ , Yutong Wang ₁ , Yuxin Li ₂ , Yucheng Gu ₃ , Zhong Li ₁ , Jiagao Cheng ₁ , Xiaoyong Xu ₁

Affiliation

为了开发具有新化学型的邻氨基苯甲酸二酰胺，设计并合成了一系列具有丙烯酰胺连接体的邻氨基苯甲酸二酰胺。初步生物测定结果表明，具有单氟烯烃酰胺接头（Z-异构体）的化合物对鳞翅目害虫表现出良好的杀幼虫活性。化合物A23对Mythimna separata和Plutella xylostella的LC ₅₀值分别为1.44和3.48 mg·L ^–1，而对氯虫苯甲酰胺的LC 50 值分别为0.08和0.06 mg·L ^–1。化合物A23对耐药菌株和易感菌株也表现出相同水平的致死效力草地贪夜蛾50 mg·L ^–1。化合物A23在试验幼虫中表现出与氯虫苯甲酰胺相似的症状。进行比较分子场分析以证明构效关系。中枢神经元钙成像实验表明，单氟烯烃化合物是潜在的兰尼碱受体 (RyR) 激活剂，可激活内质网和细胞膜中的钙通道。分子对接表明A23与小菜蛾RyR的结合能力优于氯虫苯甲酰胺。A23与小菜蛾RyR的MM|GBSA dG结合值为117.611 kcal·mol ^–1. 首次将单氟烯烃引入邻氨基苯甲酸二酰胺杀虫剂中，为昆虫 RyR 激活剂带来了新的化学型。探索了氟烯烃作为杀虫剂片段的可行性。

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Anthranilic Diamides Containing Monofluoroalkene Amide Linkers as Potential Insect RyR Activators: Design, Synthesis, Bio-evaluation, and Computational Study

In order to develop anthranilic diamides with novel chemotypes, a series of anthranilic diamides with acrylamide linkers were designed and synthesized. The results of preliminary bioassays indicated that compounds with a monofluoroalkene amide linker (Z-isomer) exhibited good larvicidal activity against lepidopteran pests. The LC₅₀ values of compound A23 against Mythimna separata and Plutella xylostella were 1.44 and 3.48 mg·L^–1, respectively, while those of chlorantraniliprole were 0.08 and 0.06 mg·L^–1, respectively. Compound A23 also exhibited the same level of lethal potency against resistant and susceptible strains of Spodoptera frugiperda at 50 mg·L^–1. Compound A23 exhibited similar symptoms as chlorantraniliprole in test larvae. Comparative molecular field analysis was conducted to demonstrate the structure–activity relationship. Central neuron calcium imaging experiments indicated that monofluoroalkene compounds were potential ryanodine receptor (RyR) activators and activated calcium channels in both the endoplasmic reticulum and the cell membrane. Molecular docking suggested that A23 had a better binding potency to P. xylostella RyR than chlorantraniliprole. The MM|GBSA dG bind value of A23 with P. xylostella RyR was 117.611 kcal·mol^–1. Monofluoroalkene was introduced into anthranilic diamide insecticides for the first time and brought a novel chemotype for insect RyR activators. The feasibility of fluoroalkenes as insecticide fragments was explored.

更新日期：2023-02-03

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