Crystal Structures, Vibrational Spectra, and Fungicidal Activity of 1,5-Diaryl-3-oxypyrazoles

Molecules

Yi Li²  Yuanyuan Liu³  Yihuang Xiong¹ 

[1] Department of Materials Science and Engineering, the Pennsylvania State University, University Park, Pennsylvania, PA 16802, USA; E-Mail:;College of Food Science and Light Industry, Nanjing University of Technology, Nanjing 211816, China; E-Mail:;Department of Chemical and Pharmaceutical Engineering, Southeast University ChengXian College, Nanjing 210088, China

关键词: 1;    5-diaryl-3-oxypyrazoles;    crystal structure;    fungicidal activity;    structure-activity relationship;   

DOI  :  10.3390/molecules19011302

来源: mdpi

【 摘 要 】

The aryloxypyrazole structure is present in a number of bioactive molecules. Four 1,5-diaryl-3-oxypyrazoles containing benzoyl (I), thiazolidinethione (II and III) or per-O-acetylated glucopyranosyl (IV) moieties were characterized by single-crystal X-ray diffraction. Compounds I and II crystallize in a triclinic P-1 system, whereas III and IV crystallize in an orthorhombic Pbca and a monoclinic P2₁ space groups, respectively. The dihedral angles between the two benzene rings of the pyrazole are 61.33° (I), 62.87° (II), 57.09° (III) and 70.25° (IV). The structures were stabilized by classical intra- (C-H···S for II and III, C-H···O for IV) and intermolecular (C-H···O for I and IV) H-bonds, as well as intermolecular C-H···π stacking interactions. The theoretical FTIR results showed good agreement with the experimental data. Compounds IV, II and III showed moderate fungicidal activity against Sclerotinia sclerotiorum and Gibberella zeae. The structure-activity relationships were discussed.

【 授权许可】

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