李益豪, 许磊川, 张倩, 马好运, 安鑫鲲, 王明安. 含稠杂环结构的螺环丁烯内酯类化合物的合成及杀菌活性[J]. 农药学学报, 2022, 24(5): 1152-1161. DOI: 10.16801/j.issn.1008-7303.2022.0077
    引用本文: 李益豪, 许磊川, 张倩, 马好运, 安鑫鲲, 王明安. 含稠杂环结构的螺环丁烯内酯类化合物的合成及杀菌活性[J]. 农药学学报, 2022, 24(5): 1152-1161. DOI: 10.16801/j.issn.1008-7303.2022.0077
    LI Yihao, XU Leichuan, ZHANG Qian, MA Haoyun, AN Xinkun, WANG Mingan. Synthesis and fungicidal activities of spirocyclic butenolide derivatives containing fused heterocyclic moiety[J]. Chinese Journal of Pesticide Science, 2022, 24(5): 1152-1161. DOI: 10.16801/j.issn.1008-7303.2022.0077
    Citation: LI Yihao, XU Leichuan, ZHANG Qian, MA Haoyun, AN Xinkun, WANG Mingan. Synthesis and fungicidal activities of spirocyclic butenolide derivatives containing fused heterocyclic moiety[J]. Chinese Journal of Pesticide Science, 2022, 24(5): 1152-1161. DOI: 10.16801/j.issn.1008-7303.2022.0077

    含稠杂环结构的螺环丁烯内酯类化合物的合成及杀菌活性

    Synthesis and fungicidal activities of spirocyclic butenolide derivatives containing fused heterocyclic moiety

    • 摘要: 为了发现更高杀菌活性的螺环丁烯内酯类化合物并分析该类化合物的构效关系,设计并合成了一系列未见文献报道的含咪唑并噻唑、咪唑并噻嗪和咪唑并噻嗪酮等稠杂环结构的螺环丁烯内酯类化合物,其结构通过核磁共振氢谱 (1H NMR)、碳谱 (13C NMR)及高分辨质谱 (HRMS)确证。离体杀菌活性测试结果表明,化合物 5f6f 对油菜菌核病菌的EC50值分别为33.2和29.8 mg/L,优于对照药剂咪唑菌酮(46.8 mg/L),化合物 7b7e 对辣椒疫霉的EC50值分别为45.8和43.5 mg/L,优于咪唑菌酮(50.7 mg/L),与先导化合物相比,其杀菌活性高于2-甲硫基衍生物,低于2-芳氨基衍生物,表明稠杂环的引入可以提高化合物的杀菌活性,而结构中的NH片段对杀菌活性具有关键作用。

       

      Abstract: In order to find compounds with higher fungicidal activity and analyze the structure-activity relationship of spirocyclic butenolide compounds, a series of novel spirocyclic butenolide derivatives containing fused heterocyclic moiety such as imidazo2,1-bthiazol-5(6H)-one, imidazo2,1-b1,3thiazin-3(2H)-one and imidazo 2,1-b1,3thiazine-3,6(2H,7H)-dione were designed and synthesized using spirocyclic butenolide as the orientation structure. Their structures were characterized by 1H NMR, 13C NMR and HRMS spectral data. The in vitro fungicidal activity evaluation results showed that the EC50 values of compounds 5f and 6f against Sclerotinia sclerotiorum were 33.2 and 29.8 mg/L, respectively, which were better than that of the commercial fungicide fenamidone (46.8 mg/L). While the EC50 values of compounds 7b and 7e against Phytophthora capsici were 45.8 and 43.5 mg/L, which were also better than that of fenamidone (50.7 mg/L). Comparison with lead compounds, their fungicidal activities were higher than that of 2-methylthio analogues and lower than that of 2-arylamino analogues, which indicated that introduction of the fused heterocyclic moiety can improve the fungicidal activities, and the NH group in the structure play a key role in the fungicidal activity.

       

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