Design, Synthesis and Biological Activity of N-Sulfonyl Aromatic Amide Derivatives

LIU Wen-Rui, HUA Xue-Wen*, ZHOU Sha, YUAN Feng-Ying, WANG Gui-Qing*, LIU Yi and XING Xiao-Ran

Chin. J. Struct. Chem. 2021, 40, 666-674  DOI: 10.14102/j.cnki.0254-5861.2011-2991

May 15, 2021

heterocyclic amide, synthesis, crystal structure, fungicidal activity, nematicidal activity

ABSTRACT

Fifteen novel N-sulfonyl aromatic amide derivatives were designed and synthesized, and the structures were characterized by 1H- and 13C-NMR, EA and HRMS. The crystal structures of compounds I-8 and I-9 were obtained from X-ray diffraction: I-8 is of triclinic system, Mr = 372.35, space group P21/n with a = 7.9151(10), b = 8.5637(11), c = 12.2022(15) Å, β = 86.865(2)º, V = 807.09(18) Å3, Z = 2, F(000) = 384, Dc = 1.532 g/cm3, the final R = 0.0408 and wR = 0.1068 for 2836 unique reflections with 2435 observed ones (I > 2σ(I)). I-9 belongs to triclinic system, Mr = 407.39, space group P21/n, with a = 8.4911(8), b = 8.6053(9), c = 14.5808(15) Å, β = 77.1190(10)º, V = 995.44(17) Å3, Z = 2, F(000) = 416, Dc = 1.359 g/cm3, the final R = 0.0567 and wR = 0.1779 for 3475 unique reflections with 2392 observed ones (I > 2σ(I)). The preliminary bioassay results indicated that the target compounds showed weak nematicidal activity, while compound I-5 displayed good fungicidal activity against Colletotrichum capsici with the inhibition rate of 61.7%.

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