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

doi:10.6023/cjoc201906017

Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (12): 3574-3582.DOI: 10.6023/cjoc201906017 Previous Articles Next Articles

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

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

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).

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Abstract

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

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Geng Rui, Zhao Yu, Li Yihao, Liu Xinlei, Wang Ming'an. Synthesis and Fungicidal Activity of Novel Pyrazole-4-carbox-amide Compounds Containing Tertiary Alcohol Moiety[J]. Chinese Journal of Organic Chemistry, 2019, 39(12): 3574-3582.

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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

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

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