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有机化学
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有机化学 ›› 2007, Vol. 27 ›› Issue (10): 1268-1272. 上一篇    下一篇

研究论文

4,5-二氢咪唑并[1,2-b]-1',2',4'-三唑-4-酮衍生物的合成与杀菌活性

付伯桥，袁菊珍，丁明武*   

  1. (华中师范大学农药与化学生物学教育部重点实验室 武汉 430079)
  • 收稿日期:2006-09-13 修回日期:2007-01-31 发布日期:2007-09-28
  • 通讯作者: 丁明武

Synthesis and Fungicidal Activities of 4,5-Dihydroimidazo[1,2-b]- 1',2',4'-triazol-4-ones

FU Bo-Qiao,YUAN Ju-Zhen,DING Ming-Wu*   

  1. (Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, Central China Normal Univer-sity,
    Wuhan 430079)
  • Received:2006-09-13 Revised:2007-01-31 Published:2007-09-28
  • Contact: DING Ming-Wu

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应用芳基异氰酸酯与烯基膦亚胺1的氮杂Wittig反应, 得到的碳二亚胺2, 再与水合肼作用得到氨基咪唑啉酮衍生物4. 而后用4与芳基异氰酸酯(或酰氯)、三苯基膦、六氯乙烷和三乙胺“一锅”反应, 得到4,5-二氢咪唑并[1,2-b]-1',2',4'-三唑-4-酮衍生物6或7. 探讨了所合成新型稠杂环化合物的生物活性, 结果表明部分化合物表现出良好的杀菌活性. 如7c在50 mg/L浓度时, 对棉花枯萎菌、稻瘟菌、黄瓜灰霉菌和油菜菌核菌的抑制率均达100%.

关键词: 4,5-二氢咪唑并[1,2-b]-1',2',4'-三唑-4-酮, 氮杂Wittig反应, 杀菌活性, 碳二亚胺

The carbodiimides 2, obtained from aza-Wittig reactions of vinyl iminophosphorane 1 with aromatic isocyanates, reacted with hydrazine to give 1-amino-2-arylamino-4-arylidene-4,5-dihy-dro-imidazol- 5-ones (4). One-pot reactions of 4 with isocyanates (or acyl chlorides), triphenyl phosphine, hexachloroethane and triethylamine produced 2-anilino (or methyl)-5-arylidene-1-aryl-4,5-dihydroimidazo[1,2-b]- 1',2',4'-triazol-4-ones 6 (or 7) in good yields. The biological activities of the new heterocycles synthesized were investigated and the results showed that some of the compounds exhibited good fungicidal activities. For example, 7c exhibited 100% inhibition against Fusarium oxysporum, Pyricularia oryzae, Botrytis Cinerea Pers., and Sclerotinia sclerotiorum de Bary at 50 mg/L.

Key words: aza-Wittig reaction, carbodiimide, fungicidal activity, 4,5-dihydroimidazo[1,2-b]-1',2',4'-triazol-4-one