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有机化学 ›› 2012, Vol. 32 ›› Issue (10): 1993-1998.DOI: 10.6023/cjoc201204026 上一篇    下一篇

研究简报

5-亚环己基-2-取代氨基咪唑啉酮类化合物的合成及其杀菌活性研究

雷建平, 韩金涛, 徐志红, 董宏波, 王明安   

  1. 中国农业大学应用化学系 北京 100193
  • 收稿日期:2012-04-25 修回日期:2012-05-30 发布日期:2012-06-06
  • 通讯作者: 王明安 E-mail:wangma@cau.edu.cn
  • 基金资助:

    国家“12×5”科技支撑计划(No. 2011BAE06B04)、国家自然科学基金(No. 21172254)和南开大学元素有机化学国家重点实验室开放基金(Nos. 0902, 201003)资助项目.

Synthesis and Fungicidal Activity of 5-Cyclohexylidene-2- aminoimidazolin-4-one Derivatives

Lei Jianping, Han Jintao, Xu Zhihong, Dong Hongbo, Wang Mingan   

  1. Department of Applied Chemistry, China Agricultural University, Beijing 100193
  • Received:2012-04-25 Revised:2012-05-30 Published:2012-06-06
  • Supported by:

    Project supported by the National Key Technologies R&D Program (No. 2011BAE06B04), the National Natural Science Foundation of China (No. 201172254) and the National Key Laboratory of Elemento-Organic Chemistry in Nankai University (Nos. 0902, 201003).

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以环己酮和2-硫代乙内酰脲为起始原料, 经Knoevenagel缩合反应制得5-亚环己基-2-硫代咪唑啉-4-酮(1), 化合物1在乙醇钠/乙醇体系中与碘甲烷反应得到5-亚环己基-2-甲硫基咪唑啉-4-酮(2), 化合物2再与相应的取代苯胺或苄胺在冰醋酸体系中回流制得目标化合物5-亚环己基-2-取代氨基咪唑啉酮3a～3r, 它们的化学结构经1H NMR, IR, MS和X-ray单晶衍射确证. 5-亚环己基-2-对氯苄氨基咪唑啉酮(3q): Mr＝335.83, C16H18ClN3O·CH4O, Monoclinic, P2(1)/n, ρ＝1.264 g/cm3, F(000)＝712, Z＝4, a＝0.59895(12) nm, b＝1.2161(2) nm, c＝2.4289(5) nm, β＝94.03(3)°. 初步生物活性测定结果表明: 在50 μg/mL浓度下, 部分目标化合物均对供试菌种显现出一定的抑制活性, 其中5-亚环己基-2-对氟苄氨基咪唑啉酮(3p)对油菜菌核的EC50为24.37 μg/mL, 3q对辣椒疫霉的EC50为28.68 μg/mL.

关键词: 5-亚环己基-2-氨基取代咪唑啉酮, 2-硫代乙内酰脲, Knoevenagel缩合反应, 杀菌活性

A series of new 5-cyclohexylidene-2-aminoimidazolin-4-one derivatives 3a～3r were synthesized via Knoevenagel condensation, methylation and substitution reaction using cyclohexanone and 2-thiohydantoin as starting material. Their structures of compounds 3a～3r were confirmed by 1 H NMR, IR, MS techniques and X-ray diffraction. 5-Cyclohexylidene- 2-p-chlorobenzylaminoimidazolin-4-one (3q): Mr＝335.83, C16H18ClN3O·CH4O, Monoclinic, P2(1)/n, ρ＝1.264 g/cm3, F(000)＝712, Z＝4, a＝0.59895(12) nm, b＝1.2161(2) nm, c＝2.4289(5) nm, β＝94.03(3)°. The preliminary bioassay shows that some of the compounds have certain fungicidal activities at the concentration of 50 μg/mL. The EC50 value of 5-cyclohexylidene-2-p-fluorobenzylaminoimidazolin-4-one (3p) against Sclerotinia scleotiorum is 24.37 μg/mL, and that of 3q against Phytophthora capsici is 28.68 μg/mL, respectively.

Key words: 5-cyclohexylidene-2-aminoimidazolin-4-one, 2-thiohydantoin, Knoevenagel reaction, fungicidal activity