Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (1): 229-235.DOI: 10.6023/cjoc202206008 Previous Articles     Next Articles



孙昌兴, 张福豪, 张欢, 李鹏辉, 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:2022-06-07 修回日期:2022-07-11 发布日期:2022-09-01
  • 通讯作者: 姜林
  • 基金资助:

Design, Synthesis, Fungicidal Activity and Molecular Docking Study of Novel 2-(1-Methyl-1H-pyrazol-4-yl)pyrimidine-4-carboxamides

Changxing Sun, Fuhao Zhang, Huan Zhang, Penghui Li, Lin Jiang()   

  1. College of Chemistry and Material Science, Shandong Agricultural University, Tai'an, Shandong 271018
  • Received:2022-06-07 Revised:2022-07-11 Published:2022-09-01
  • Contact: Lin Jiang
  • Supported by:
    Natural Science Foundation of Shandong Province(ZR2020MB110)

Abstract In order to develop novel pyrimidine fungicides, thirteen 2-(1-methyl-1H-pyrazol-4-yl) pyrimidine-4-carboxami- des were synthesized from 2-chloropyrimidine-4-carboxylic acid, 1-methyl-4-pyrazole borate pinacol ester, substituted anilines or substituted benzylamines as starting materials. The structures of target compounds were characterized by 1H NMR, 13C NMR, IR, HRMS, and the crystal structure of N-benzyl-2-(1-methyl-1H-pyrazol-4-yl)pyrimidine-4-carboxamide (4h) was also determined by X-ray diffraction method. The preliminary fungicidal activities against three plant fungi were evaluated, and the results showed that at a dosage of 100 mg/L, N-(4-methyl)phenyl-2-(1-methyl-1H-pyrazol-4-yl)pyrimidine-4-carboxamide (4f) and N-(4-chlorobenzyl)-2-(1-methyl-1H-pyrazol-4-yl)pyrimidine-4-carboxamide (4j) possessed relatively high activities against Rhizoctonia solani with inhibitory rates of 85.3% and 79.1%, respectively. Molecular docking study showed that 4f can form two hydrogen bonds and one cation-π interaction with succinate dehydrogenase.

Key words: pyrimidine, carboxamide, succinate dehydrogenase (SDHI), fungicidal activity, molecular docking