Abstract
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.
Highlights
Since the discovery of the fungicide pyraclostrobin by BASF scientists [1,2,3], aryloxypyrazoles have attracted enormous attention due to their diverse bioactivities in fungicide [4,5], insecticide [6], and herbicide [7]
We have devoted considerable effort to develop this series of fungicide, and found several 1,5-diaryl-3-oxypyrazoles containing alkyloxyacetate, heterocycle, glucopyranosyl or benzoyl moieties with fungicidal activity [8,9,10,11,12]
We report the crystal structures and FTIR spectra of four 1,5-diaryl-3-oxypyrazoles bearing benzoyl (I), thiazolidinethione (II and III) or per-O-acetylated glucopyranosyl (IV) moieties (Figure 1)
Summary
Since the discovery of the fungicide pyraclostrobin by BASF scientists [1,2,3], aryloxypyrazoles have attracted enormous attention due to their diverse bioactivities in fungicide [4,5], insecticide [6], and herbicide [7]. We have devoted considerable effort to develop this series of fungicide, and found several 1,5-diaryl-3-oxypyrazoles containing alkyloxyacetate, heterocycle, glucopyranosyl or benzoyl moieties with fungicidal activity [8,9,10,11,12]. Their detailed structural properties and structure-activity relationship have not been reported. We report the crystal structures and FTIR spectra of four 1,5-diaryl-3-oxypyrazoles bearing benzoyl (I), thiazolidinethione (II and III) or per-O-acetylated glucopyranosyl (IV) moieties (Figure 1) Their in vitro fungicidal activity against Sclerotinia sclerotiorum and Gibberella zeae has been investigated, and their structure-activity relationshipe were discussed
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