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

Molecules

Xiaohui Xiong¹  Yi Li¹  Yuanyuan Liu²  Yihuang Xiong³ 

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

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

DOI  :  10.3390/molecules19011302

来源: DOAJ

【 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】

Unknown