Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (2): 650-656.DOI: 10.6023/cjoc202307029 Previous Articles     Next Articles


李鹏辉, 谢青洋, 万福贤, 张元红, 姜林*()   

  1. 山东农业大学化学与材料科学学院 山东泰安 271018
  • 收稿日期:2023-07-31 修回日期:2022-09-17 发布日期:2023-10-12
  • 作者简介:
  • 基金资助:

Synthesis and Fungicidal Activity of Novel Substituted Pyrimidine-5-carboxamides Bearing Cyclopropyl Moiety

Penghui Li, Qingyang Xie, Fuxian Wan, Yuanhong Zhang, Lin Jiang()   

  1. College of Chemistry and Material Science, Shandong Agricultural University, Tai'an, Shandong 271018
  • Received:2023-07-31 Revised:2022-09-17 Published:2023-10-12
  • Contact: E-mail:
  • About author:
    These authors contributed equally to this work.
  • Supported by:
    Natural Science Foundation of Shandong Province(ZR2020MB110)

In order to develop novel pyrimidine compounds with excellent fungicidal activity, thirteen N-substituted phenyl-2- cyclopropyl-4-methylpyrimidine-5-carboxamides and three analogues without cyclopropyl moiety were designed and synthesized by means of the active substructure splicing method. The structures of target compounds were characterized by1H nuclear magnetic resonance (1H NMR), 13C nuclear magnetic resonance (13C NMR), infrared spectrometry (IR) and high-resolution mass spectra (HRMS). The preliminary fungicidal activities against plant fungi were evaluated, and the result revealed that some compounds exhibited high activity at a concentration of 100 mg/L. For example, N-(4-chlorophenyl)- 2-cyclopropyl-4-methylpyrimidine-5-carboxamide(4e), N-(4-brorophenyl)-2-cyclopropyl-4-methylpyrimidine-5-carboxamide (4h) and N-(3,4-dichlorophenyl)-2-cyclopropyl-4-methylpyrimidine-5-carboxamide(4k) showed inhibitory rates of 87.9%, 84.4% and 85.2% against Botrytis cinerea, respectively, and 4k showed inhibitory rate of 84.6% against Sclerotinia sclerotiorum. Further bioassay indicated that 4k possessed a lower effective concentration value of 4.67 mg/L, which meant that its activity was comparable to that of cyprodimol and was higher than that of boscalid. A bioactivity comparison between target compounds and the analogues without cyclopropyl moiety, demonstrated that the intrduction of cyclopropyl to the pyrimidine ring is beneficial for improving the fungicidal activity.

Key words: pyrimidine, cyclopropyl, amide, synthesis, fungicidal activity