State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), College of Chemistry, Nankai University, Tianjin 300071, China; College of Horticulture and Landscape Architecture, Tianjin Agricultural University, Tianjin 300384, China.
State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), College of Chemistry, Nankai University, Tianjin 300071, China.
Bioorg Med Chem. 2018 Jul 23;26(12):3541-3550. doi: 10.1016/j.bmc.2018.05.028. Epub 2018 May 19.
A series of novel anthranilic diamides derivatives (7a-s) containing halogen, trifluoromethyl group and cyano group were designed, synthesized, and characterized by melting point, H NMR, C NMR and elemental analyses. The bioactivity revealed that most of them showed moderate to excellent activities against oriental armyworm (Mythimna separata) and diamondback moth (Plutella xylostella). Above all, the larvicidal activity of 7o against oriental armyworm was 100% and 40% at 0.25 and 0.1 mg L, comparable to that of the standard chlorantraniliprole (100%, 0.25 mg L and 20%, 0.1 mg L). What is more, 7o against diamondback moth displayed 90% insecticidal activity at 0.01 mg L, superior to chlorantraniliprole (45%, 0.01 mg L). The experiments 7o on the American cockroach (Periplaneta Americana) heart beating rates (Dorsal vessel) and contractile force were compared with chlorantraniliprole. In addition, 7o could affect the calcium homeostasis in the central neurons of the third larvae of oriental armyworm, which revealed that the ryanodine receptor is the potential target of 7o. The density functional theory (DFT) calculation results revealed the amide bridge, the benzene ring of anthraniloyl moiety and pyrazole ring might play an important role in the insecticidal activity through hydrophobic interactions and π-π conjugations.
一系列新型邻苯二甲酰亚胺二酰胺衍生物（7a-s）被设计、合成并通过熔点、1H NMR、13C NMR 和元素分析进行了表征。生物活性测试表明，它们中的大多数对东方粘虫（Mythimna separata）和小菜蛾（Plutella xylostella）表现出中等至优异的活性。尤其是，7o 对东方粘虫的杀虫活性在 0.25 和 0.1 mg/L 时达到 100%和 40%，与标准氯虫苯甲酰胺（100%，0.25 mg/L 和 20%，0.1 mg/L）相当。更重要的是，7o 对小菜蛾在 0.01 mg/L 时表现出 90%的杀虫活性，优于氯虫苯甲酰胺（45%，0.01 mg/L）。实验中，7o 对美洲大蠊（Periplaneta Americana）的心率（背血管）和收缩力与氯虫苯甲酰胺进行了比较。此外，7o 可以影响东方粘虫幼虫 3 龄中枢神经元的钙稳态，这表明肌醇 1,4,5-三磷酸受体是 7o 的潜在靶标。密度泛函理论（DFT）计算结果表明，酰胺桥、邻苯二甲酰亚胺部分的苯环和吡唑环可能通过疏水相互作用和π-π共轭在杀虫活性中发挥重要作用。
