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合成、杀虫评价及含硫部分新型邻苯二甲酰胺衍生物作为潜在的兰尼碱受体激活剂的作用模式。

Synthesis, insecticidal evaluation and mode of action of novel anthranilic diamide derivatives containing sulfur moiety as potential ryanodine receptor activators.

机构信息

College of Chinese Materia Medica, Tianjin University of Traditional Chinese Medicine, Tianjin 300193, China.

College of Horticulture and Landscape Architecture, Tianjin Agricultural University, Tianjin 300384, China.

出版信息

Bioorg Med Chem. 2019 Mar 1;27(5):769-776. doi: 10.1016/j.bmc.2019.01.009. Epub 2019 Jan 16.

DOI:10.1016/j.bmc.2019.01.009
PMID:30679133
Abstract

Anthranilic diamide insecticide could control lepidopteran pests by selectively binding and activating insect ryanodine receptors (RyRs), and the unique mode of action is different from other conventional insecticides. In order to discover new anthranilic diamide insecticide as ryanodine receptors activators, a series of 11 novel anthranilic diamides derivatives (Ia-k) were synthesized and confirmed by melting point, H NMR, C NMR and elemental analyses. The preliminary bioactivity revealed that most title compounds showed moderate to remarkable activities against oriental armyworm (Mythimna separata) and diamondback moth (Plutella xylostella). Especially, compounds Ia and If, which exhibited 100% larvicidal activity against oriental armyworm at 1.0 mg L, and comparable to that of chlorantraniliprole (100% at 1 mg L). If displayed 60% insecticidal activity against diamondback moth at 0.01 mg L, better than chlorantraniliprole (45% at 0.01 mg L). The preliminary structure activity relationships were discussed. In addition, the calcium imaging experiment indicated that the insect ryanodine receptor is the potential target of If.

摘要

邻苯二甲酰胺类杀虫剂可以通过选择性结合和激活昆虫肌浆网钙释放通道(RyRs)来控制鳞翅目害虫,其独特的作用方式与其他常规杀虫剂不同。为了发现新型邻苯二甲酰胺类杀虫剂作为肌浆网钙释放通道激活剂,我们合成了一系列 11 种新型邻苯二甲酰胺类衍生物(Ia-k),并通过熔点、1H NMR、13C NMR 和元素分析进行了确证。初步的生物活性测试表明,大多数标题化合物对东方粘虫(Mythimna separata)和小菜蛾(Plutella xylostella)表现出中等至显著的活性。特别是化合物 Ia 和 If,它们对东方粘虫的杀虫活性达到 100%(在 1.0mg/L 时),与氯虫苯甲酰胺(在 1mg/L 时为 100%)相当。If 对小菜蛾的杀虫活性为 60%(在 0.01mg/L 时),优于氯虫苯甲酰胺(在 0.01mg/L 时为 45%)。我们还讨论了初步的构效关系。此外,钙成像实验表明,肌浆网钙释放通道是 If 的潜在靶标。

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