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Novel Fluorinated Aniline Anthranilic Diamides Improved Insecticidal Activity Targeting the Ryanodine Receptor
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2022-08-19 , DOI: 10.1021/acs.jafc.2c03134
Jinzhou Ren 1, 2 , Haolin Yuan 1, 2 , Xiaoyu Liu 1, 2 , Zhenwu Yu 1, 2 , Fanfei Meng 1, 2 , Lixia Xiong 1, 2 , Na Yang 1, 2 , Yuxin Li 1, 2 , Zhengming Li 1, 2 , Zhijin Fan 1, 2
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2022-08-19 , DOI: 10.1021/acs.jafc.2c03134
Jinzhou Ren 1, 2 , Haolin Yuan 1, 2 , Xiaoyu Liu 1, 2 , Zhenwu Yu 1, 2 , Fanfei Meng 1, 2 , Lixia Xiong 1, 2 , Na Yang 1, 2 , Yuxin Li 1, 2 , Zhengming Li 1, 2 , Zhijin Fan 1, 2
Affiliation
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The diamide insecticides show exceptional activity against Lepidoptera insects via activation of ryanodine receptors (RyRs). In the present study, a series of anthranilic diamides containing a fluoroaniline moiety were designed, synthesized, and evaluated for insecticidal potency. Most titled compounds exerted moderate to remarkably high activity against Mythimna separata, Plutella xylostella, and Spodoptera frugiperda. The insecticidal activity of compound II l and II ac against M. separata was 26.7 and 26.7% at 0.1 mg L–1, respectively, equivalent to that of chlorantraniliprole (0.1 mg L–1, 30.0%). Compounds II l, II y, and II z exhibited 8.0-, 1.8-, and 4.7-fold higher potency than chlorantraniliprole against P. xylostella, respectively, as compared with their LC50s. Compounds II k and II aa showed good insecticidal activity against S. frugiperda with LC50 of 0.56 and 0.46 mg L–1, respectively, comparable to that of the commercial insecticide chlorantraniliprole with LC50 of 0.31 mg L–1. Calcium imaging experiments indicated RyRs as the action target. Molecular docking suggested a higher binding energy of 8.647 kcal/mol between II l and the M. separata RyR than the 7.820 kcal/mol between chlorantraniliprole and the M. separata RyR. Meanwhile, the docking results of II l with mutated P. xylostella RyR at site G4946E showed that II l could have a good inhibition effect on the resistant P. xylostella. The density functional theory calculations suggested the importance of the fluoroaniline moiety in potency. Those novel anthranilic diamides containing a fluorinated aniline moiety are good insecticidal candidates.
中文翻译：
新型氟化苯胺邻氨基苯甲酸二酰胺提高了针对瑞安定受体的杀虫活性
二酰胺类杀虫剂通过激活兰尼碱受体 (RyRs)对鳞翅目昆虫表现出非凡的活性。在本研究中，设计、合成了一系列含有氟苯胺部分的邻氨基苯甲酸二酰胺，并对其杀虫效力进行了评估。大多数标题化合物对Mythimna separata、Plutella xylostella和Spodoptera frugiperda具有中等至非常高的活性。化合物II l和II ac在 0.1 mg L -1时对M. separata的杀虫活性分别为26.7% 和 26.7% ，相当于氯虫苯甲酰胺（0.1 mg L -1, 30.0%)。与 LC 50 s相比，化合物II l、II y和II z分别比氯虫苯甲酰胺对小菜蛾的效力高 8.0 倍、1.8 倍和 4.7 倍。化合物II k和II aa对S. frugiperda表现出良好的杀虫活性，LC 50分别为 0.56 和 0.46 mg L -1，与商业杀虫剂氯虫苯甲酰胺的 LC 50为 0.31 mg L -1相当. 钙成像实验表明 RyRs 是作用靶点。分子对接表明IIl和M. separata RyR之间的结合能为8.647 kcal/mol，高于氯虫苯甲酰胺和M. separata RyR之间的7.820 kcal/mol 。同时， IIl与突变小菜蛾RyR在G4946E位点的对接结果表明，IIl对抗性小菜蛾具有良好的抑制作用。密度泛函理论计算表明氟苯胺部分在效力中的重要性。那些含有氟化苯胺部分的新型邻氨基苯甲酸二酰胺是很好的杀虫候选物。
更新日期：2022-08-19
中文翻译：
新型氟化苯胺邻氨基苯甲酸二酰胺提高了针对瑞安定受体的杀虫活性
二酰胺类杀虫剂通过激活兰尼碱受体 (RyRs)对鳞翅目昆虫表现出非凡的活性。在本研究中，设计、合成了一系列含有氟苯胺部分的邻氨基苯甲酸二酰胺，并对其杀虫效力进行了评估。大多数标题化合物对Mythimna separata、Plutella xylostella和Spodoptera frugiperda具有中等至非常高的活性。化合物II l和II ac在 0.1 mg L -1时对M. separata的杀虫活性分别为26.7% 和 26.7% ，相当于氯虫苯甲酰胺（0.1 mg L -1, 30.0%)。与 LC 50 s相比，化合物II l、II y和II z分别比氯虫苯甲酰胺对小菜蛾的效力高 8.0 倍、1.8 倍和 4.7 倍。化合物II k和II aa对S. frugiperda表现出良好的杀虫活性，LC 50分别为 0.56 和 0.46 mg L -1，与商业杀虫剂氯虫苯甲酰胺的 LC 50为 0.31 mg L -1相当. 钙成像实验表明 RyRs 是作用靶点。分子对接表明IIl和M. separata RyR之间的结合能为8.647 kcal/mol，高于氯虫苯甲酰胺和M. separata RyR之间的7.820 kcal/mol 。同时， IIl与突变小菜蛾RyR在G4946E位点的对接结果表明，IIl对抗性小菜蛾具有良好的抑制作用。密度泛函理论计算表明氟苯胺部分在效力中的重要性。那些含有氟化苯胺部分的新型邻氨基苯甲酸二酰胺是很好的杀虫候选物。
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