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Synthesis and biological evaluation of arylpyrazoles as fungicides against phytopathogenic fungi

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Abstract

3-phenol-1H-pyrazoles (2), 4-halogeno-3-phenol-1H-pyrazoles (3) and 2-(1-phenol-1H-pyrazol-5-yl)phenols (4) were prepared by the condensation of (E)-3-(dimethylamino)-1-phenylprop-2-en-1-ones and hydrazine hydrate or phenylhydrazine in good yields. They were evaluated against five phytopathogens fungi, namely Cytospora sp., Colletotrichum gloeosporioides, Botrytis cinerea, Alternaria solani and Fusarium solani in vitro. Most of the above-mentioned compounds exhibited activities. For example, 4-chloro-2-(1H-pyrazol-3-yl)phenol (3k) and 4-bromo-3-phenol-1H-pyrazole (3b) showed good and broad-spectrum antifungal properties against Cytospora sp., C. gloeosporioides, Botrytis cinerea, Alternaria solani and F. Solani with \(\hbox {IC}_{50}\) values ranging from 4.66 to 12.47 \(\upmu \)g/mL. The results showed that pyrazoles with one aryl group at 3-position (2 and 3) exhibited better antibacterial activity than those with two aryl substituents (4). In addition, the existence of an electron-withdrawing group, a substituent on the ortho-position of phenol ring or a halogen atom at the 4-position of the pyrazole enhanced the antifungal activity of pyrazoles 2 and 3.

Graphical Abstract

A series of arylpyrazole derivatives was facilely prepared and was evaluated against five phytopathogens fungi including Cytospora sp., Colletotrichum gloeosporioides, Botrytis cinerea, Alternaria solani, and Fusarium solani in vitro. Most of those compounds exhibited remarkable antifungal activities and were superior to the positive control hymexazol.

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Acknowledgements

This research was supported by the National Natural Science Foundation of China (No: 21542002) and also supported by the Fundamental Research Funds for the Central Universities (NO. 2016CBY002).

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Authors and Affiliations

  1. Key Laboratory of the Ministry of Education for Medicinal Resources and Natural Pharmaceutical Chemistry, National Engineering Laboratory for Resource Development of Endangered Crude Drugs in Northwest of China, and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi’an, 710062, People’s Republic of China

    Jin Zhang, Ju-Fang Peng, Tao Wang, Yang Kang, Sisi Jing & Zun-Ting Zhang

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  1. Jin Zhang
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  2. Ju-Fang Peng
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  3. Tao Wang
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  4. Yang Kang
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  6. Zun-Ting Zhang
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Correspondence to Zun-Ting Zhang.

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Zhang, J., Peng, JF., Wang, T. et al. Synthesis and biological evaluation of arylpyrazoles as fungicides against phytopathogenic fungi. Mol Divers 21, 317–323 (2017). https://doi.org/10.1007/s11030-017-9727-x

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