有机化学 ›› 2015, Vol. 35 ›› Issue (2): 411-421.DOI: 10.6023/cjoc201409043 上一篇    下一篇

研究论文

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).

通过酰氯制备异硫氰酸酯, 与5-(4-氨基苄基)-2,4-咪唑啉二酮反应合成了含2,4-咪唑啉二酮的N-苯甲酰基-N'-苯基硫脲, 然后在三乙胺存在下再与溴丙酮发生碱催化缩合反应以中等以上收率合成了新型含2,4-咪唑啉二酮的4-甲基- 3-苯基-2-酰亚胺噻唑啉, 它们的化学结构经1H NMR, IR, HR-ESI-MS和化合物3g4g的X-ray单晶衍射表征, 硫脲与溴丙酮的反应机理通过化合物3g4g的晶体结构得到进一步确证. 初步生物活性测定结果表明: 部分目标化合物对供试昆虫及菌种显现出良好的抑制活性, 如在200 mg/L浓度下化合物3i4q对小菜蛾的死亡率分别为86%和100%, 在50 mg/L浓度下化合物4n对油菜菌核菌的抑制率为82.6%, 而它们对油菜和稗草显示出微弱但并不特征的除草活性.

关键词: 2,4-咪唑啉二酮, 4-甲基-3-苯基-2-酰亚胺噻唑啉, 杀菌活性, 杀虫活性

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