Novel Anthranilic Diamide Scaffolds Containing N-Substituted Phenylpyrazole as Potential Ryanodine Receptor Activators

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• 作者：Jing-Bo Liu ; Yu-Xin Li ; Xiu-Lan Zhang ; Xue-Wen Hua ; Chang-Chun Wu ; Wei Wei ; Ying-Ying Wan ; Dan-Dan Cheng ; Li-Xia Xiong ; Na Yang ; Hai-Bin Song ; Zheng-Ming Li
• 刊名：Journal of Agricultural and Food Chemistry
• 出版年：2016
• 出版时间：May 11, 2016
• 年：2016
• 卷：64
• 期：18
• 页码：3697-3704
• 全文大小：488K
• 年卷期：0
• ISSN：1520-5118

文摘

To discover potent insecticides targeting ryanodine receptors (RyRs), a series of novel anthranilic diamides analogues (12a–12u) containing N-substituted phenylpyrazole were designed and synthesized. These compounds were characterized by ¹H NMR, ¹³C NMR, and HRMS, and the structure of compound 12u was confirmed by X-ray diffraction. Their insecticidal activities indicated that these compounds displayed moderate to excellent activities. In particular, 12i showed 100 and 37% larvicidal activities against oriental armyworm (Mythimna separata) at 0.25 and 0.05 mg L^–1, equivalent to that of chlorantraniliprole (100%, 0.25 mg L^–1; and 33%, 0.05 mg L^–1). The activity of 12i against diamondback moth (Plutella xylostella) was 95% at 0.05 mg L^–1, whereas the control was 100% at 0.05 mg L^–1. The calcium-imaging technique experiment results showed that the effects of 12i on the intracellular calcium ion concentration ([Ca²⁺]_i) in neurons were concentration-dependent. After the central neurons of Helicoverpa armigera were dyed by loading with fluo-5N and treated with 12i, the free calcium released in endoplasmic reticulum indicated the target of compound 12i is RyRs or IP₃Rs. The activation of RyRs by natural ryanodine completely blocked the calcium release induced by 12i, which indicated that RyRs in the central neurons of H. armigera third-instar larvae is the possible target of compound 12i.