Abstract
In order to find amide compounds with desired antifungal activity, 16 nicotinamide derivatives containing diphenylamine moieties were prepared by condensation of 2-chloronicotinic acid with substituted N1-phenylbenzene-1,2-diamines based on the structure of fungicide boscalid. The structures of the synthesized compounds were characterized by 1H NMR, 13C NMR, ESI-MS, and elemental analysis. Among the compounds screened, compound 3a had high inhibitory effects against Rhizoctonia solani in vitro and in vivo, which slightly exceeded boscalid. The study of the structure-activity relationship provides important information for further structural optimization. Molecular docking offered a reasonable explanation to guarantee its fungicidal activity against R. solani. These results could provide a benchmark for understanding the antifungal activity against the phytopathogenic fungus R. solani and prompt us to develop more potent fungicides.
Graphical abstract
Sixteen nicotinamide derivatives containing diphenylamine moieties were prepared based on the structure of fungicide boscalid. Thereinto, compound 3a showed high antifungal activity against Rhizoctonia solani. Structure-activity relationship study provided important information for further structural optimization. Molecular docking offered a reasonable explanation to guarantee its fungicidal activity.
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Acknowledgements
This work was supported by the Natural Science Research Key Project of the Universities of Anhui Province, China (Grant No. KJ2020A0334). University-level key projects of Anhui University of science and technology (Grant No. QN2019107). The Collaborative Innovation Project of Colleges and Universities of Anhui Province (Grant No. GXXT-2020-058).
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Yan, Z., Liu, S., Qiu, L. et al. Design, synthesis, and antifungal activity of nicotinamide derivatives containing diphenylamine moieties. J Chem Sci 134, 87 (2022). https://doi.org/10.1007/s12039-022-02081-x
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DOI: https://doi.org/10.1007/s12039-022-02081-x