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有机化学
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有机化学 ›› 2004, Vol. 24 ›› Issue (11): 1413-1416. 上一篇    下一篇

研究论文

2-烷硫基-4-芳基亚甲基-5-氢-1-苯氨基-1H-咪唑啉-5-酮的合成与杀菌活性

陈云峰, 黄年玉, 丁明武*   

  1. 华中师范大学化学学院 教育部农药与化学生物学重点实验室 武汉 430079
  • 收稿日期:2004-02-27 修回日期:2004-04-19 接受日期:2004-05-11 发布日期:2022-09-21
  • 通讯作者: * E-mail: ding5229@yahoo.com.cn
  • 基金资助:
    国家重点基础研究发展规划(Nos. 2003CB114400, 2003CB114406)及国家自然科学基金(No. 20102001)资助项目.

Synthesis and Fungicidal Activities of 2-Alkylthio-4-arylmethylene-5- hydro-1-phenylamino-1H-imidazol-5-ones

CHEN Yun-Feng, HUANG Nian-Yu, DING Ming-Wu*   

  1. Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, Collegeof Chemistry, Central China Normal University, Wuhan 430079
  • Received:2004-02-27 Revised:2004-04-19 Accepted:2004-05-11 Published:2022-09-21

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应用CS2与烯基膦亚胺1的氮杂Wittig反应,得到的异硫氰酸酯2再与苯肼作用得到氨基硫脲3,而后用3与卤代烷在K2CO3的作用下反应直接得到2-烷硫基-4-芳基亚甲基-5-氢-1-苯氨基-1H-咪唑啉-5-酮衍生物4.探讨了反应的条件以及合成的新型杂环化合物的生物活性,结果表明部分化合物表现出较好的杀菌活性.如4e在50 mg/L浓度时,对黄瓜灰霉菌的抑制率为87%.

关键词: 咪唑啉酮, 氮杂Wittig反应, 异硫氰酸酯, 合成, 杀菌活性

Isothiocyanates (2), obtained fromaza-Wittig reaction of vinyliminophosphoranes (1) with CS2, reacted with phenylhydrazine to give thiosemicarbazides (3).2-Alkylthio-4-arylmethylene-5-hydro-1-phenylamino-1H-imidazol-5-ones (4) were directly prepared by reaction of 3 with alkyl halide in the presence of K2CO3. The reaction conditions for cyclization and biological activities of the new heterocycles synthesized were investigated. The results showed that some of the compounds exhibited good fungicidal activities. For example, 4e exhibited 87% inhibition of Botrytis Cinerea Pers. in 50 mg/L.

Key words: 1H-imidazol-5-one, aza-Wittig reaction, isothiocyanate, synthesis, fungicidal activity