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Design, synthesis, and insecticidal evaluation of novel anthranilic diamides of N-pyridylpyrazole derivatives containing 3-thioethers
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2021-12-03 , DOI: 10.1002/jhet.4422
Pengwei Sun 1 , Ze Zhang 1 , Linshan Li 1 , Xinyao Wang 1 , Lixia Xiong 1 , Na Yang 1 , Yuxin Li 1 , Zhengming Li 1
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2021-12-03 , DOI: 10.1002/jhet.4422
Pengwei Sun 1 , Ze Zhang 1 , Linshan Li 1 , Xinyao Wang 1 , Lixia Xiong 1 , Na Yang 1 , Yuxin Li 1 , Zhengming Li 1
Affiliation
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Thioether and its derivatives are important active pharmacophores, widely adopted in the molecular design of agrochemicals. The introduction of thioether into drug intermediate is important to improve the liposolubility, hydrophobicity, and bioactivity of molecules. For development of novel insecticides targeting at ryanodine receptor (RyR), a series of anthranilic diamides of N-pyridylpyrazole derivatives containing 3-thioether were designed and synthesized. The structures of these compounds were verified using 1H NMR, 13C NMR, and HRMS. Their insecticidal activities against Mythimna separata (M. separata, oriental armyworms) and Plutella xylostella (P. xylostella, diamondback moths) were evaluated and the preliminary structure–activity relationship (SAR) was discussed, among which 9f, 9g exhibited favorable insecticidal activities against M. separata at 5 mg/L (9f, 50%; 9g, 40%). In addition, insecticidal activity of the intermediate 8 indicated that bromomethyl group at 3-position of pyrazole moiety has an important impact for retaining insecticidal activity. Calcium imaging experiment and molecular docking were carried out to elaborate insecticidal mechanism from the perspective of experiment and molecular simulation, respectively.
中文翻译：
含有 3-硫醚的 N-吡啶基吡唑衍生物的新型邻氨基苯甲酸二酰胺的设计、合成和杀虫评价
硫醚及其衍生物是重要的活性药效团，广泛应用于农用化学品的分子设计。将硫醚引入药物中间体对于提高分子的脂溶性、疏水性和生物活性具有重要意义。为了开发针对兰尼碱受体（RyR）的新型杀虫剂，设计并合成了一系列含有3-硫醚的N-吡啶基吡唑衍生物邻氨基苯甲酸二酰胺。使用1 H NMR、13 C NMR 和 HRMS验证这些化合物的结构。它们对Mythimna separata ( M. separata , oriental粘虫) 和Plutella xylostella ( P. xylostella )的杀虫活性, 小菜蛾) 进行了评价并讨论了初步的构效关系 (SAR), 其中9f , 9g在 5 mg/L ( 9f , 50%; 9g , 40%)对M. separata表现出良好的杀虫活性。此外，中间体8的杀虫活性表明吡唑部分3位溴甲基对保持杀虫活性有重要影响。钙成像实验和分子对接分别从实验和分子模拟的角度阐述了杀虫机理。
更新日期：2021-12-03
中文翻译：
含有 3-硫醚的 N-吡啶基吡唑衍生物的新型邻氨基苯甲酸二酰胺的设计、合成和杀虫评价
硫醚及其衍生物是重要的活性药效团，广泛应用于农用化学品的分子设计。将硫醚引入药物中间体对于提高分子的脂溶性、疏水性和生物活性具有重要意义。为了开发针对兰尼碱受体（RyR）的新型杀虫剂，设计并合成了一系列含有3-硫醚的N-吡啶基吡唑衍生物邻氨基苯甲酸二酰胺。使用1 H NMR、13 C NMR 和 HRMS验证这些化合物的结构。它们对Mythimna separata ( M. separata , oriental粘虫) 和Plutella xylostella ( P. xylostella )的杀虫活性, 小菜蛾) 进行了评价并讨论了初步的构效关系 (SAR), 其中9f , 9g在 5 mg/L ( 9f , 50%; 9g , 40%)对M. separata表现出良好的杀虫活性。此外，中间体8的杀虫活性表明吡唑部分3位溴甲基对保持杀虫活性有重要影响。钙成像实验和分子对接分别从实验和分子模拟的角度阐述了杀虫机理。
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