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| Synthesis,X-ray Structure aSynthesis,X-ray Structure and Bioactivity of N-4-Methyl-1,2,3-thiadiazole-5-carbonyl-N′-3,5- dichloro-4-(1,1,2,2-tetrafluoroethoxyl)phenyl Urea | |
| 引用本文： | GUO Dan-Dan,WANG Dun,FAN Zhi-Jin,LI Juan-Juan,SONG Hai-Bin,FAN Qian. Synthesis,X-ray Structure aSynthesis,X-ray Structure and Bioactivity of N-4-Methyl-1,2,3-thiadiazole-5-carbonyl-N′-3,5- dichloro-4-(1,1,2,2-tetrafluoroethoxyl)phenyl Urea[J]. 结构化学, 2012, 31(12) |
| 作者姓名： | GUO Dan-Dan WANG Dun FAN Zhi-Jin LI Juan-Juan SONG Hai-Bin FAN Qian |
| 基金项目： | This study was funded in part by grants from the National Natural Science Foundation of China，the Natural Science Foundation of Tianjin，thc National Kcy Project for Basic Research，the National Key Tcchnology Research and Development Program，the Foundation of Achievements Transformation and Spreading of Tianjin Agricultural Science and Technology，Tianjin Key Technology Research and Dcvcloprncnt Program (11ZCGYNC0010 |
| 摘 要： | The title compound N-4-methyl-1,2,3-thiadiazole-5-carbonyl-N?-3,5-dichloro-4- (1,1,2,2- tetrafluoroethoxyl)phenyl urea (C13H8Cl2F4N4O3S, Mr = 447.19) has been synthesized from 4-methyl- 1,2,3-thiadiazole-5-carbonyl chloride as the starting material, and its structure was characterized by proton Nuclear Magnetic Resonance (1H NMR), Infra Red Spectroscopy (IR), high-resolution mass spectroscopy (HRMS), and single-crystal X-ray diffraction. The crystal of the title compound belongs to triclinic, space group P with a = 6.0780(8), b = 11.3760(14), c = 12.1440(18) , α = 96.887(7), β = 91.027(12), γ = 104.252(13)°, Z = 2, V = 806.98(19) ·3, Dc = 1.840 g/cm3, μ = 0.601 mm-1, F(000) = 448, R = 0.0450 and wR = 0.0869. X-ray analysis indicates that the 1,2,3-thiadiazole ring is not coplanar with the phenyl ring, and the dihedral angle is 33.57°. Two intermolecular hydrogen bonds N(2)-H…O(1), S(1)…H-C(11), and three weak intermolecular interactions, C(11)…O(1), N(1)…O(2) and S…O(1), are observed. The bioassay results indicate that the title compound has good insecticidal activity against Culex pipiens pallens and good induction activity for tobacco against tobacco mosaic virus which is equal to that of TDL. |
| 关 键 词： | 生物活性 噻二唑 苯基脲 羰基 合成 结构 抗烟草花叶病毒 单晶X-射线衍射 |
Synthesis, X-ray Structure and Bioactivity of N-4-Methyl-1,2,3-thiadiazole-5-carbonyl-N'-3,5- dichloro-4-(1,1,2,2-tetrafluoroethoxyl)phenyl Urea |
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| Affiliation: | 1. State Key Laboratory of Elemento Organic Chemistry, Nankai University, Tianjin 300071, China 2. Sichuan Functional Heterocyclic Compounds Engineering Technology Research Center, Lier Chemicals Co., Ltd., No. 97 Mianxingdonglu, Mianyang, Sichuan 621000, China 3. The Ural Federal University Named after the First President ofRussia B. N. Yeltsin, Yeltsin UrFU 620002, Ekaterinburg, Russia |
| Abstract: | The title compound N-4-methyl-1,2,3-thiadiazole-5-carbonyl-N?-3,5-dichloro-4- (1,1,2,2- tetrafluoroethoxyl)phenyl urea (C13H8Cl2F4N4O3S, Mr = 447.19) has been synthesized from 4-methyl- 1,2,3-thiadiazole-5-carbonyl chloride as the starting material, and its structure was characterized by proton Nuclear Magnetic Resonance (1H NMR), Infra Red Spectroscopy (IR), high-resolution mass spectroscopy (HRMS), and single-crystal X-ray diffraction. The crystal of the title compound belongs to triclinic, space group P with a = 6.0780(8), b = 11.3760(14), c = 12.1440(18) , α = 96.887(7), β = 91.027(12), γ = 104.252(13)°, Z = 2, V = 806.98(19) ·3, Dc = 1.840 g/cm3, μ = 0.601 mm-1, F(000) = 448, R = 0.0450 and wR = 0.0869. X-ray analysis indicates that the 1,2,3-thiadiazole ring is not coplanar with the phenyl ring, and the dihedral angle is 33.57°. Two intermolecular hydrogen bonds N(2)-H…O(1), S(1)…H-C(11), and three weak intermolecular interactions, C(11)…O(1), N(1)…O(2) and S…O(1), are observed. The bioassay results indicate that the title compound has good insecticidal activity against Culex pipiens pallens and good induction activity for tobacco against tobacco mosaic virus which is equal to that of TDL. |
| Keywords: | crystal structure 1 2 3-thiadiazole synthesis biological activity |
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