State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, P. R. China.
Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University, Tianjin 300071, P. R. China.
J Agric Food Chem. 2024 Apr 10;72(14):8072-8080. doi: 10.1021/acs.jafc.3c08759. Epub 2024 Mar 28.
To increase the structural diversity of insecticides and meet the needs of effective integrated insect management, the structure of chlorantraniliprole was modified based on a previously established three-dimensional quantitative structure-activity relationship (3D-QSAR) model. The pyridinyl moiety in the structure of chlorantraniliprole was replaced with a 4-fluorophenyl group. Further modifications of this 4-fluorophenyl group by introducing a halogen atom at position 2 and an electron-withdrawing group (e.g., iodine, cyano, and trifluoromethyl) at position 5 led to 34 compounds with good insecticidal efficacy against , , and . Among them, compound against showed potency comparable to that of chlorantraniliprole. against displayed a 4.5 times higher potency than chlorantraniliprole. In addition, and chlorantraniliprole exhibited comparable potencies against . Transcriptome analysis showed that the molecular target of compound is the ryanodine receptor. Molecular docking was further performed to verify the mode of action and insecticidal activity against resistant .
为了增加杀虫剂的结构多样性并满足有效综合虫害管理的需求，基于先前建立的三维定量构效关系（3D-QSAR）模型，对氯虫苯甲酰胺的结构进行了修饰。在氯虫苯甲酰胺的结构中，用 4-氟苯基取代了吡啶基部分。通过在 4-氟苯基的 2 位引入卤素原子和 5 位引入吸电子基团（如碘、氰基和三氟甲基），进一步修饰这个 4-氟苯基，得到了 34 种对 、 、 具有良好杀虫活性的化合物。其中，化合物 对 的杀虫活性与氯虫苯甲酰胺相当。化合物 对 的杀虫活性比氯虫苯甲酰胺高 4.5 倍。此外，化合物 对 的杀虫活性与氯虫苯甲酰胺相当，而对 的杀虫活性则比氯虫苯甲酰胺高 4.5 倍。转录组分析表明，化合物 的分子靶标是肌醇 1,4,5-三磷酸受体。进一步进行分子对接以验证其对抗性 的作用方式和杀虫活性。
