Synthesis, Crystal Structure and Biological Activity of N-(2,6-Difluorobenzoyl)-N’-[5-(4-trifluoromethylphenyl)-1,3,4-thiadiazol-2-yl]urea
邵 宇;杨 平;李世荣;王发松;胡卫兵
湖北民族学院
Synthesis, Crystal Structure and Biological Activity of N-(2,6-Difluorobenzoyl)-N΄[5-(4-trifluoromethyl- phenyl)-1,3,4-thiadiazol-2-yl]ure
SHAO Yu; YANG Ping; LI Shi-Rong;;WANG Fa-Song HU Wei-Bing
Key Laboratory of Biological Resources Protection and Utilization of Hubei Province, School of Chemical and Environmental Engineering, Hubei University for Nationalities, Enshi
摘要The title compound N-(2,6-difluorobenzoyl)-N΄-[5-(4-trifluoromethylphenyl)-1,3,4- thiadiazol-2-yl]urea (C17H9F5N4O2S, Mr= 428.34) has been synthesized by the reaction of 2-amino-5-(4-trifluoromethylphenyl)-1,3,4-thiadiazole with 2,6-difluorobenzoyl isocyanate, and its crystal structure was determined by single-crystal X-ray diffraction. The crystal belongs to monoclinic, space group P21/n with a = 10.7316(13), b = 10.5617(13), c = 16.037(2) Å,b= 106.408(2)°, V = 1743.6(4) Å3, Z = 4, Dc= 1.632 g/cm3, μ = 0.260 mm-1, F(000) = 864, the final R = 0.0599 and wR= 0.1420 for 3467 observed reflections with I > 2s(I). The urea group, which adopts a planar configuration mediated by the intramolecular N–H···O hydrogen bond, is nearly coplanar with the thiadiazole and 4-trifluoromethylbenzene rings. The title compound was found to exhibit good fungicidal activity against Rhizoctonia solani and Botrytis cinerea.
The title compound N-(2,6-difluorobenzoyl)-N΄-[5-(4-trifluoromethylphenyl)-1,3,4- thiadiazol-2-yl]urea (C17H9F5N4O2S, Mr= 428.34) has been synthesized by the reaction of 2-amino-5-(4-trifluoromethylphenyl)-1,3,4-thiadiazole with 2,6-difluorobenzoyl isocyanate, and its crystal structure was determined by single-crystal X-ray diffraction. The crystal belongs to monoclinic, space group P21/n with a = 10.7316(13), b = 10.5617(13), c = 16.037(2) Å,b= 106.408(2)°, V = 1743.6(4) Å3, Z = 4, Dc= 1.632 g/cm3, μ = 0.260 mm-1, F(000) = 864, the final R = 0.0599 and wR= 0.1420 for 3467 observed reflections with I > 2s(I). The urea group, which adopts a planar configuration mediated by the intramolecular N–H···O hydrogen bond, is nearly coplanar with the thiadiazole and 4-trifluoromethylbenzene rings. The title compound was found to exhibit good fungicidal activity against Rhizoctonia solani and Botrytis cinerea.
2011, Vol. 30 
