Crystal Structures Vibrational Spectra and Fungicidal Activity of 15-Diaryl-3-oxypyrazoles

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.