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有机化学.pdfVIP

2007 年第 27 卷 有 机 化 学 Vol. 27, 2007 第 10 期, 1268～1272 Chinese Journal of Organic Chemistry No. 10, 1268～1272 ·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 (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) 摘要 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 (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; 碳二亚胺; 杀菌活性 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* (Key Laboratory of Pesticide Chemical Biology of Ministry of Education, Central China Normal University, Wuhan 430079) Abstract The carbodiimides 2, obtained from aza-Wittig reactions of vinyl iminophosphorane 1 with aro- matic isocyanates, reacted with hydrazine to give 1-amino-2-arylamino-4-arylidene-4,5-dihydro-imidazol- 5-ones (4). One-pot reactions of 4 with isocyanates (or acyl chlorides), triphenyl phosphine, hexachloro- ethane 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 c