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Molecules 2014, 19(1), 1302-1316; doi:10.3390/molecules19011302

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

2,* , 3
1 College of Food Science and Light Industry, Nanjing University of Technology, Nanjing 211816, China 2 Department of Chemical and Pharmaceutical Engineering, Southeast University ChengXian College, Nanjing 210088, China 3 Department of Materials Science and Engineering, the Pennsylvania State University, University Park, Pennsylvania, PA 16802, USA
* Authors to whom correspondence should be addressed.
Received: 4 November 2013 / Revised: 9 January 2014 / Accepted: 14 January 2014 / Published: 21 January 2014
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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.
Keywords: 1,5-diaryl-3-oxypyrazoles; crystal structure; fungicidal activity; structure-activity relationship 1,5-diaryl-3-oxypyrazoles; crystal structure; fungicidal activity; structure-activity relationship
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Li, Y.; Liu, Y.; Xiong, Y.; Xiong, X. Crystal Structures, Vibrational Spectra, and Fungicidal Activity of 1,5-Diaryl-3-oxypyrazoles. Molecules 2014, 19, 1302-1316.

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