Synthesis, Crystal Structure and Biological Activity of 1-(β-D-Glucopyranosyl)-3-amino-5-methyl-1H-1,2,4-triazole

The title compound 1-(beta-D-glucopyranosyl)-3-amino-5-methyl-1H-1,2,4-triazole was synthesized and characterized by IR, H-1-NMR and elemental analysis. Its single crystals of 2H(2)O adduct suitable for X-ray analysis were obtained by the slow evaporation of a H2O solution and its structure was determined by single-crystal X-ray diffraction. The crystal belongs to orthorhombic, space group P2(1)2(1)2(1) with a = 7.7490(15), b = 10.424(2), c = 17.447(4) angstrom, V = 1409.3(5) angstrom(3), Z = 4, C9H20N4O7, M-r = 296.29, D-c = 1.396 g/cm(3), mu = 0.120 mm(-1), S = 1.007, F(000) = 632, R = 0.0686 and wR = 0.1560 for 1217 observed reflections with I > 2 sigma(I). The title molecules are linked through intermolecular hydrogen bonds to form two 1-D chain structures, and such adjacent chains are further linked by intermolecular hydrogen bonds and H2O bridges to form a 3-D supramolecular network structure. The preliminary bioassay results showed that the title compound exhibits fungicidal activities against Gibberella zeae and Colletotrichum orbiculare.