Novel Nitrophenyl Substituted Anthranilic Diamide Derivatives: Design, Synthesis, Selectivity, and Antiresistance,Journal of Agricultural and Food Chemistry

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Novel Nitrophenyl Substituted Anthranilic Diamide Derivatives: Design, Synthesis, Selectivity, and Antiresistance
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2023-11-08 , DOI: 10.1021/acs.jafc.3c03067
Pengwei Sun ₁ , Ze Zhang ₁ , Jiahui Zhao ₂ , Hongyuan Zhang ₁ , Lianyun Lin ₂ , Xinyao Wang ₁ , Linshan Li ₁ , Peng Cao ₃ , Zhongwen Wang ₁ , Zhengming Li ₁ , Zhiguang Yuchi ₂ , Yuxin Li _{1,

4}

Affiliation

Diamide insecticides have gained popularity due to their high efficacy and low toxicity to nontarget organisms. However, diamide-associated resistance has emerged recently, causing a significant reduction in their potency, thereby hindering sustainable agricultural development. Here, we explored novel diamide insecticide analogs and, using a structure-based approach, rationally designed and synthesized 28 nitrophenyl substituted anthranilic diamides. Most of the compounds showed moderate to good activity against Mythimna separata, Plutella xylostella, and Spodoptera frugiperda. Among them, compounds Ia and Im showed extraordinarily high activity and their mode of action was verified on isolated neurons. Additionally, Im exhibited over 10-fold greater potency than chlorantraniliprole in a HEK293 cell line stably expressing S. frugiperda ryanodine receptors (SfRyRs) containing the resistance mutations, G4891E and I4734M. The binding modes of Im in the SfRyRs were predicted using in silico molecular docking analysis. Our novel nitrophenyl substituted anthranilic diamide derivatives provide valuable insights for the design of insecticidal RyR-targeting compounds to effectively control both wild type and diamide insecticide-resistant lepidopteran pests.

中文翻译：

新型硝基苯基取代的邻氨基苯甲酸二酰胺衍生物：设计、合成、选择性和抗耐药性

二酰胺杀虫剂由于其高效且对非目标生物低毒而受到欢迎。然而，最近出现了与二酰胺相关的抗性，导致其效力显着降低，从而阻碍了农业的可持续发展。在这里，我们探索了新型二酰胺杀虫剂类似物，并采用基于结构的方法，合理设计并合成了28个硝基苯基取代的邻氨基苯甲二酰胺。大多数化合物对粘虫、小菜蛾和草地贪夜蛾表现出中等至良好的活性。其中，化合物Ia和Im表现出极高的活性，并且它们的作用模式在分离的神经元上得到了验证。此外，在稳定表达含有抗性突变 G4891E 和 I4734M 的草地贪夜蛾兰尼碱受体 ( Sf RyRs)的 HEK293 细胞系中，Im的效力比氯虫苯甲酰胺高 10 倍以上。使用计算机分子对接分析预测Im在Sf RyR 中的结合模式。我们的新型硝基苯基取代的邻氨基苯甲酸二酰胺衍生物为杀虫 RyR 靶向化合物的设计提供了宝贵的见解，以有效控制野生型和对二酰胺杀虫剂具有抗性的鳞翅目害虫。

更新日期：2023-11-08

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