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    杨帅, 唐豪毅, 赵晨, 等. 含有伯酰胺和氰基的苯基噻唑衍生物的设计、合成及杀虫活性评价[J]. 华南农业大学学报, 2024, 45(3): 354-363. doi: 10.7671/j.issn.1001-411X.202308001
    引用本文: 杨帅, 唐豪毅, 赵晨, 等. 含有伯酰胺和氰基的苯基噻唑衍生物的设计、合成及杀虫活性评价[J]. 华南农业大学学报, 2024, 45(3): 354-363. doi: 10.7671/j.issn.1001-411X.202308001
    shu
    YANG Shuai, TANG Haoyi, ZHAO Chen, et al. Design, synthesis and evaluation of insecticidal activity of phenylthiazole derivative containing primary amide and cyanogroup[J]. Journal of South China Agricultural University, 2024, 45(3): 354-363. doi: 10.7671/j.issn.1001-411X.202308001
    Citation: YANG Shuai, TANG Haoyi, ZHAO Chen, et al. Design, synthesis and evaluation of insecticidal activity of phenylthiazole derivative containing primary amide and cyanogroup[J]. Journal of South China Agricultural University, 2024, 45(3): 354-363. doi: 10.7671/j.issn.1001-411X.202308001
    shu

    含有伯酰胺和氰基的苯基噻唑衍生物的设计、合成及杀虫活性评价

    Design, synthesis and evaluation of insecticidal activity of phenylthiazole derivative containing primary amide and cyanogroup

      摘要
    • 摘要:
      目的 噻唑是一类具有广泛生物活性的五元杂环化合物，本文设计并合成一系列含有伯酰胺及氰基的苯基噻唑衍生物，进一步挖掘噻唑骨架在防治鳞翅目害虫领域的潜力。
      方法 以不同取代基的苯甲酸为原料合成含有伯酰胺及氰基的噻唑衍生物，并经1H NMR、13C NMR和ESI-MS确证结构。采用浸液法测定目标化合物对小菜蛾Plutella xylostella的生物活性，并通过密度泛函理论(Density functional theory，DFT)计算从分子轨道层面解释该骨架具有杀虫活性的原因和差异。
      结果 经结构确证，合成了22个含有伯酰胺及氰基的噻唑衍生物，其中6个化合物(6d、7d、13a、13b、14a和14b)对小菜蛾表现出很好的杀虫活性(校正死亡率 > 50%)，尤其是化合物6d和7d，对小菜蛾的LC50达到了23.94和30.37 mg/L。构效关系表明，苯环仅取代4−CF3且5−位噻唑未取代时，表现出最优的杀虫活性。DFT计算结果表明，4−三氟甲基苯基噻唑既传递电子又接受电子，且化合物6d比7d具有更小的HOMO−LUMO间隙(ΔE)。
      结论 化合物6d可作为先导化合物进一步开发，本研究可为含有噻唑骨架杀虫剂的分子设计与优化提供有价值的线索。

       

      Abstract:
      Objective Thiazole is a class of five-membered heterocyclic compounds with a wide range of biological activities, which are widely used in the fields of medicine and agrochemicals. In this paper, we designed and synthesized a series of phenyl thiazole derivatives containing primary amide and cyanogroup to further explore the potential of thiazole scaffold in controlling Lepidoptera pests.
      Method The new thiazole derivatives containing primary amide and cyanogroup were synthesized from benzoic acid with different substituent, and the structures were confirmed by 1H NMR, 13C NMR and ESI-MS. The biological activities of target products against Plutella xylostella were determined by the leaf immersion method. The density functional theory (DFT) calculation was used to explain the reason and difference of insecticidal activity of this skeleton at the molecular orbital level.
      Result The results of structural verification showed 22 thiazole derivatives containing primary amide and cyanogroup were synthesized. Six compounds (6d, 7d, 13a, 13b, 14a and 14b) showed good insecticidal activities (mortality > 50%) against P. xylostella, especially the compounds of 6d and 7d with LC50 of 23.94 and 30.37 mg/L respectively. The structure-activity relationship showed the optimal insecticidal activity was demonstrated for benzene ring monosubstituted 4-CF3 and 5-position thiazole unsubstituted. The results of DFT calculation showed that 4-(trifluoromethyl) phenyl thiazole both delivered and received electrons, and the compound 6d has a smaller HOMO−LUMO gap (ΔE) than 7d.
      Conclusion The compound 6d can be further developed as a lead compound. This research provides a valuable clue for molecule design and optimization of insecticide containing thiazole scaffold.

       

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