Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2021 Nov;25(4):2379-2388.
doi: 10.1007/s11030-020-10127-w. Epub 2020 Jul 30.

Synthesis of pyrazole-4-carboxamides as potential fungicide candidates

Cuntao Dong #  1 , Wei Gao #  1 , Xiaotian Li  1 , Susu Sun  1 , Jingqian Huo  1 , Yanen Wang  1 , Da Ren  1 , Jinlin Zhang  2 , Lai Chen  3
Affiliations

Synthesis of pyrazole-4-carboxamides as potential fungicide candidates

Cuntao Dong et al. Mol Divers. 2021 Nov.

Abstract

A series of novel pyrazole-4-carboxamides were rationally designed, synthesized, and their structures were characterized by 1H NMR, 13C NMR and HRMS. Preliminary bioassay showed that four compounds 8g, 8j, 8o and 8s exhibited more than 90% and even completed inhibition against Alternaria solani at 100 μg/mL; and 8d displayed 100% inhibition against Fusarium oxysporum at the same concentration. Moreover, 8j exhibited good in vitro fungicidal activity against A. solani with EC50 value of 3.06 μg/mL, and it also displayed completed in vivo protective antifungal activity against A. solani on tomato at 10 mg/L, as boscalid did. The molecular docking results indicated that 8j exhibited the high affinity with SDH protein by H-bond and π-π stacking interactions, which may explain the reasons for its good activities. These data support that compound 8j could be used as a fungicide candidate for further study. A practical method for the synthesis of pyrazole-4-carboxamides were provided and evaluation of their antifungal activities.

Keywords: Fungicidal activity; Molecular docking; Pyrazole carboxamide; Succinate dehydrogenase inhibitor; Synthesis.

PubMed Disclaimer

References

    1. Lamberth C (2018) Agrochemical lead optimization by scaffold hopping. Pest Manage Sci 74(2):282–292. https://doi.org/10.1002/ps.4755 - DOI
    1. Chen L, Wu Q, Fan Z, Li H, Li J, Hu W, Liu X, Belskaya NP, Glukhareva T, Zhao B (2018) Design, synthesis and biological evaluation of isothiazole based 1,2,4-trizaole derivatives. Chin J Chem 36(8):731–736. https://doi.org/10.1002/cjoc.201700765 - DOI
    1. Bardas GA, Veloukas T, Koutita O, Karaoglanidis GS (2010) Multiple resistance of Botrytis cinerea from kiwi fruit to SDHIs, QoIs and fungicides of other chemical groups. Pest Manag Sci 66(9):967–973. https://doi.org/10.1002/ps.1968 - DOI - PubMed
    1. He L, Cui K, Song Y, Mu W, Liu F (2018) High-efficiency control of gray mold by the novel SDHI fungicide benzovindiflupyr combined with a reasonable application approach of dipping flower. J Agric Food Chem 66(26):6692–6698. https://doi.org/10.1021/acs.jafc.8b01936 - DOI - PubMed
    1. Ishii H, Zhen F, Hu M, Li X, Schnabel G (2016) Efficacy of SDHI fungicides, including benzovindiflupyr, against Colletotrichum species. Pest Manage Sci 72(10):1844–1853. https://doi.org/10.1002/ps.4216 - DOI

MeSH terms

Supplementary concepts

LinkOut - more resources