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Synthesis, antifungal activity and mechanism of action of novel chalcone derivatives containing 1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazole

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Abstract

A series of chalcone derivatives containing 1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazole was designed and synthesized. Structures of all compounds were characterized by 1H NMR, 13C NMR, 19F NMR, and HRMS. The biological activities of the compounds were determined with the mycelial growth rate method, and further studies showed that some compounds had good antifungal activities at the concentration of 100 μg/mL. The EC50 value of compound L31 was 15.9 μg/mL against Phomopsis sp., which were better than that of azoxystrobin (EC50 value was 69.4 μg/mL). In addition, the mechanism of action of compound L31 shown that compound can affect mycelial growth by disrupting membrane integrity against Phomopsis sp., and that the higher the concentration of the compound is, the greater the disruption of membrane integrity is.

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Acknowledgements

The authors gratefully acknowledge the National Nature Science Foundation of China (No. 32072446), the Science Foundation of Guizhou Province (No. 20192452), National Key Technology Research and Demonstration Project of Hubei Agricultural Science and Technology Innovation Center (No. 202062000000207), and Key Research and Development Program of China (No. 2019YFD1002000).

Funding

National Natural Science Foundation of China, No. 32072446,Wei Xue, Natural Science Foundation of Guizhou Province,20192452, Wei Xue, Hubei Agricultural Science and Technology Innovation Center, No. 202062000000207, Hua Wang, Hebei Provincial Key Research Projects, No. 2019YFD1002000, Hua Wang.

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  1. Wenliang Zhan and Ran Zhou have contributed equally to this work.

Authors and Affiliations

  1. State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering; Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education; Research and Development Center for Fine Chemicals, Guizhou University, Guiyang, 550025, People’s Republic of China

    Wenliang Zhan, Ran Zhou, Piao Mao, Chunmei Yuan, Tao Zhang, Yi Liu, Jiao Tian & Wei Xue

  2. Institute of Plant Protection and Soil Fertility, Hubei Academy of Agricultural Sciences, Wuhan, 430064, People’s Republic of China

    Hua Wang

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  1. Wenliang Zhan
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Zhan, W., Zhou, R., Mao, P. et al. Synthesis, antifungal activity and mechanism of action of novel chalcone derivatives containing 1,2,4-triazolo-[3,4-b]-1,3,4-thiadiazole. Mol Divers 28, 461–474 (2024). https://doi.org/10.1007/s11030-022-10593-4

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