Regioselective Synthesis, Crystal Structure and Biological Activity of Novel 2-Phenylsulfonylhydrazono-3-(3-trifluoromethylphenyl)-2(3H)-thiazoline Derivatives  

作　　者：陈伟 王浩安 魏巍 李玉新 华学文 宋海斌 于淑晶 李正名 

机构地区：[1]State Key Laboratory of Elemento-organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University [2]Tianjin Nankai High School

出　　处：《Chinese Journal of Structural Chemistry》2015年第4期503-509,共7页结构化学（英文）

基　　金：supported by the National Natural Science Foundation of China(No.21272129);the National Key Technologies R&D Program(2011BAE06B05)

摘　　要：The title compounds 2-phenylsulfonylhydrazono-3-（3-trifluoromethylphenyl）-2（3H）- thiazoline derivatives were designed and synthesized via the reaction of thiosemicarbazides with chloroacetaldehyde, and their chemical structures were characterized by ^1H NMR, ^13C NMR, elemental analysis and MS. Furthermore, 4a was characterized by single-crystal X-ray diffraction. The target compound 4a （C16H12F3N302S2, Mr = 399.41） crystallized in monoclinic system, P21/c space group with a = 7.7457（4）, b = 13.5850（7）, c = 16.5455（10） A, β= 99.698（2）°, V= 1656.30（16） A3, Dc = 1.602 g/cm^3, Z = 4, F（000） = 816, λ = 0.71070 A,μ（MoKa） = 0.370 mm^-1, R = 0.072 and wR = 0.0867. The crystal structure of 4a revealed the cyclization of thiosemicarbazide moiety with chloroacetaldehyde at the N（l） position. The title compounds exhibited good insecticidal activity against spider mite （Tetranychus cinnabarinus Boisduval） and favorable fungicidal activity against Corynespora cassiicola.The title compounds 2-phenylsulfonylhydrazono-3-（3-trifluoromethylphenyl）-2（3H）- thiazoline derivatives were designed and synthesized via the reaction of thiosemicarbazides with chloroacetaldehyde, and their chemical structures were characterized by ^1H NMR, ^13C NMR, elemental analysis and MS. Furthermore, 4a was characterized by single-crystal X-ray diffraction. The target compound 4a （C16H12F3N302S2, Mr = 399.41） crystallized in monoclinic system, P21/c space group with a = 7.7457（4）, b = 13.5850（7）, c = 16.5455（10） A, β= 99.698（2）°, V= 1656.30（16） A3, Dc = 1.602 g/cm^3, Z = 4, F（000） = 816, λ = 0.71070 A,μ（MoKa） = 0.370 mm^-1, R = 0.072 and wR = 0.0867. The crystal structure of 4a revealed the cyclization of thiosemicarbazide moiety with chloroacetaldehyde at the N（l） position. The title compounds exhibited good insecticidal activity against spider mite （Tetranychus cinnabarinus Boisduval） and favorable fungicidal activity against Corynespora cassiicola.

关 键 词：2（3H）-thiazoline regioselective cyclization insecticidal activity fungicidal activity 

分 类 号：O626[理学—有机化学]