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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) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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