有机化学 ›› 2019, Vol. 39 ›› Issue (12): 3574-3582.DOI: 10.6023/cjoc201906017 上一篇    下一篇

研究简报

含叔醇结构的新型吡唑-4-甲酰胺类化合物的合成及杀菌活性

耿瑞, 赵宇, 李益豪, 刘鑫磊, 王明安   

  1. 中国农业大学应用化学系 北京 100193
  • 收稿日期:2019-06-17 修回日期:2019-07-08 发布日期:2019-08-01
  • 通讯作者: 王明安 E-mail:wangma@cau.edu.cn
  • 基金资助:
    国家自然科学基金(No.21772229)资助项目.

Synthesis and Fungicidal Activity of Novel Pyrazole-4-carbox-amide Compounds Containing Tertiary Alcohol Moiety

Geng Rui, Zhao Yu, Li Yihao, Liu Xinlei, Wang Ming'an   

  1. Department of Applied Chemistry, China Agricultural University, Beijing 100193
  • Received:2019-06-17 Revised:2019-07-08 Published:2019-08-01
  • Supported by:
    Project supported by the National Natural Science Foundation of China (No. 21772229).

在吡唑环的3位引入叔醇结构,设计合成了一系列新颖的吡唑-4-甲酰胺类化合物,其结构经1H NMR,13C NMR,HR-ESI-MS和X射线衍射表征确证.生物活性测试结果显示,部分化合物在100μg/mL时对瓜果腐霉菌和辣椒疫霉菌等测试植物病原菌显示了一定的杀菌活性,如N-(2-氟苯基)-3-(1-羟基环己基)-1,5-二甲基-1H-吡唑-4-甲酰胺(B1)和N-(噻唑-2-基)-3-(1-羟基环己基)-1,5-二甲基-1H-吡唑-4-甲酰胺(B10)对瓜果腐霉菌的EC50分别为76.3和71.9μg/mL,化合物B10对辣椒疫霉菌的EC50分别为85.4μg/mL.

关键词: 吡唑-4-甲酰胺, 叔醇, 合成, 杀菌活性

A series of novel pyrazole-4-carboxamide compounds were designed and synthesized through introducing a tertiary alcohol moiety into the C-3 position of the pyrazole ring based on the chracteristics of pyrazole-4-carboxamide fungicides and natural products with a tertiary alcohol moiety. Their structures were characterized by 1H NMR, 13C NMR, HR-ESI-MS data and X-ray diffraction. The preliminary bioassay results indicated that some of these compounds exhibit certain fungicidal activities against tested phytopathogens at the concentration of 100 µg/mL. N-(2-Fluorophenyl)-3-(1-hydroxycyclohexyl)-1,5-dimethyl-1H-pyrazole-4-carboxamide (B1) and N-(thiazol-2-yl)-3-(1-hydroxycyclohexyl)-1,5-dimethyl-1H-pyrazole-4-carbo-xamide (B10) have EC50 values of 76.3 and 71.9 µg/mL against Pythium aphanidermatum. B10 has an EC50 value of 85.4 µg/mL against Phytophthora capsici, respectively.

Key words: pyrazole-4-carboxamide, tertiary alcohol moiety, synthesis, fungicidal activity