Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (10): 1993-1998.DOI: 10.6023/cjoc201204026 Previous Articles     Next Articles



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
  • 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).

A series of new 5-cyclohexylidene-2-aminoimidazolin-4-one derivatives 3a3r were synthesized via Knoevenagel condensation, methylation and substitution reaction using cyclohexanone and 2-thiohydantoin as starting material. Their structures of compounds 3a3r 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