新型含硫醚、亚砜和砜的间双酰胺化合物的设计、合成和杀虫活性

    Design, synthesis and insecticidal activity of novel m-diamides containing sulfide, sulfoxide and sulfone

    • 摘要: 随着杀虫剂的出现和大量使用,害虫对杀虫剂的抗药性增强,为开发高效、低毒、环境友好型杀虫剂应对害虫耐药性威胁,采用活性亚结构拼接法,以环丙氟虫胺为先导化合物,设计并合成了18个含硫醚、亚砜和砜的新型间二酰胺类化合物,所有化合物均采用核磁共振氢谱 (1H NMR) 和高分辨质谱 (HRMS) 进行表征,并选取了部分代表性化合物通过核磁共振碳谱 (13C NMR) 表征进一步确证其结构。生物测定试验结果表明,大多数目标化合物对褐飞虱 (Nilaparvata lugens) 表现出优异的杀虫活性,尤其是12d在100 mg/L下对褐飞虱的杀虫活性为87.32%。部分化合物对朱砂叶螨 (Tetranychus cinnabarinus) 表现出较好的杀螨活性,其中10f在10 mg/L下对朱砂叶螨的杀螨活性高达100.00%。此外,根据生测活性初步讨论了构效关系。

       

      Abstract: With the emergence and widespread use of insecticides, the resistance of pests to insecticides has increased. To develop efficient, low toxicity, and environmentally friendly insecticides to address the threat of pest resistance, this work adopts the method of active substructures splicing and uses cyproflanilide as the lead compound to design and synthesize 18 novel m-diamide compounds containing thioether, sulfoxide, and sulfone. All compounds were characterized by 1H NMR and HRMS and some representative compounds were selected for 13C NMR characterization to further confirm their structures. Most target compounds exhibited excellent insecticidal activity against Nilaparvata lugens, especially 12d at 100 mg/L showing 87.32% activity against N. lugens. At the same time, some compounds also showed good activity against Tetranychus cinnabarinus, among which 10f showed 100.00% activity against T. cinnabarinus at a concentration of 10 mg/L. Based on the bioassay activity, preliminary structure-activity relationships were also discussed.

       

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