Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (2): 411-421.DOI: 10.6023/cjoc201409043 Previous Articles     Next Articles

Articles

新型含2,4-咪唑啉二酮的4-甲基-3-苯基-2-酰亚胺噻唑啉的合成及生物活性

徐志红, 董宏波, 刘斌, 孔令青, 王明安   

  1. 中国农业大学应用化学系 北京 100193
  • 收稿日期:2014-09-26 修回日期:2014-10-22 出版日期:2015-02-25 发布日期:2014-10-30
  • 通讯作者: 王明安 E-mail:wangma@cau.edu.cn
  • 基金资助:

    “十二五”科技支撑计划(No. 2011BAE06B03)和国家自然科学基金(No. 21172254)资助项目.

Synthesis and Biological Activity of Novel 4-Methyl-3-substituted-phenyl-2-benzoylimine Thiazolines with Hydantion

Xu Zhihong, Dong Hongbo, Liu Bin, Kong Lingqing, Wang Mingan   

  1. Department of Applied Chemistry, China Agricultural University, Beijing 100193
  • Received:2014-09-26 Revised:2014-10-22 Online:2015-02-25 Published:2014-10-30
  • Supported by:

    Project supported by the National Key Technologies R & D Program (No. 2011BAE06B03) and the National Natural Science Foundation of China (No. 21172254).

Novel N-benzoyl-N'-phenylthioureas containing imidazolidine-2,4-dione were prepared from substituted benzoyl chlorides via isothiocyanate formation followed by treatment with 5-(4-aminophenyl/benzyl)imidazolidine-2,4-dione. The base-catalyzed condensation of thioureas with bromoacetone was carried out in the presence of triethylamine to afford the corresponding 4-methyl-3-substituted-phenyl-2-acylimine thiazolines in moderate to good yields. The corresponding thiazolines were characterized by IR, 1H NMR, HR-ESI-MS spectroscopic data and X-ray diffraction analyses, and the mechanism of thiourea reacting with bromoacetone was re-confirmed by the X-ray structures of compounds 3g and 4g. The thiazolines were evaluated their biological activities, and some of them exhibited significant activities such as compounds 3i and 4q having 82.6% and 100% mortality against P. xylostella at the concentration of 200 mg/L, 4n having 82.6% inhibitory rate against S. scleotiorum at 50 μg/mL, and slight but not significant herbicidal activities.

Key words: hydantoin, 4-methyl-3-phenyl-2-acylimine thiazoline, antifungal activity, insecticidal activity