Crystal structures, vibrational spectra, and fungicidal activity of 1,5-diaryl-3-oxypyrazoles.
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.
College of Food Science and Light Industry, Nanjing University of Technology, Nanjing 211816, China. liynj2012@njut.edu.cn.
Yi
Y
Li
Department of Chemical and Pharmaceutical Engineering, Southeast University ChengXian College, Nanjing 210088, China. liuyuanyuan@cxxy.seu.edu.cn.
Yuanyuan
Y
Liu
Department of Materials Science and Engineering, the Pennsylvania State University, University Park, Pennsylvania, PA 16802, USA. yyx5048@psu.edu.
Yihuang
Y
Xiong
College of Food Science and Light Industry, Nanjing University of Technology, Nanjing 211816, China. xxh@njut.edu.cn.
Xiaohui
X
Xiong
D000935:Antifungal Agents / Q000737:chemistry* / Q000494:pharmacology*; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D011720:Pyrazoles / Q000737:chemistry* / Q000494:pharmacology*; D017550:Spectroscopy, Fourier Transform Infrared; D014961:X-Ray Diffraction
D000935:Antifungal Agents; D011720:Pyrazoles; C031280:pyrazole