Synthesis, Crystal Structure and Anti-fungal/Anti-oomycete  Activity of New Pyrazole-benzene Carboxamide Derivatives

YANG Zi-Hui, LIU Qing-Song, SUN Yue, SUN Xue-Bao and GU Wen*

Chin. J. Struct. Chem. 2022, 41, 2203253-2203259  DOI: 10.14102/j.cnki.0254-5861.2011-3360

March 15, 2022

pyrazole-benzene carboxamide, crystal structure, antifungal activity, anti-oomycete activity

ABSTRACT

Four novel pyrazole-benzene carboxamide derivatives 2a~2d were synthesized and characterized by NMR, HRMS spectral method and X-ray diffraction analysis, and were further conducted for screening the anti-fungal/anti-oomycete activity. Compound 2d crystallizes as monoclinic space group P21/c with a = 42.260(4), b = 5.3751(4), c = 8.0129(9) Å, β = 92.958(10)°, V = 1817.7(3) Å3, Z = 4, Mr = 385.41, Dc = 1.408 Mg/m3, S = 1.087, m = 0.773 mm-1, F(000) = 808, the final R = 0.0763 and wR = 0.2136 for 2657 observed reflections (I > 2σ(I)). The preliminary antifungal assay indicates that the title compounds show fair to excellent anti- fungal/anti-oomycete activity toward four plant fungi and two crop oomycetes. Among them, compound 2b exhibits the strongest in vitro anti-B. cinerea effects (EC50 = 1.61 mg/L). In vivo test presents compound 2b displays considerable protective and curative effects to tomato fruits infected by B. cinerea. These results indicate that compound 2b would be potential fungicides leads for further development.



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