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Synthesis, Characterization and Crystal Structure of N-(3-((2-Chlorothiazol-5-yl)methyl)-5-methyl-1,3,5-oxadiazinan-4-ylidene)nitramide
Corresponding Author(s) : Jian-Ling He
Asian Journal of Chemistry,
Vol. 27 No. 7 (2015): Vol 27 Issue 7, 2015
Abstract
N-(3-[(2-chlorothiazol-5-yl)methyl]-5-methyl-1,3,5-oxadiazinan-4-ylidene)nitramide (I), i.e., thiamethoxam, it is a broad-spectrum insecticide that effectively controls insects, being a second generation neonicotinoid compound belonging to the chemical subclass the thianicotinyls. It was prepared from 5-(chloromethyl)-2-(phenylthio)thiazole (1) via chlorination by Cl2/HCl system and then condensation by K2CO3/CsI. The product was characterized by NMR and LC-MS. The crystal structure of compound I was investigated using X-ray diffraction and SHELXTL-97 software. The result indicated that compound I crystallized in the monoclinic system, space group P 21/n with a = 6.488(13), b = 28.786 (6), c = 6.804(14) Å, V=1225.1 (5) Å3; Z4.
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- S. Al Zadjali, S. Morse, J. Chenoweth and M. Deadman, Sci. Total Environ., 476-477, 505 (2014); doi:10.1016/j.scitotenv.2013.12.040.
- J. Patil, J. Ashoka, M. Bheemanna and K. Narayana, J. Entomol. Res., 37, 207 (2013).
- Z. Yi-xuan and Z. Yi-bin, Shi Jie Nong Yao, 35, 23 (2013).
- P. Maienfisch, H. Huerlimann, A. Rindlisbacher, L. Gsell, H. Dettwiler, J. Haettenschwiler, E. Sieger and M. Walti, Pest Manage. Sci., 57, 165 (2001); doi:10.1002/1526-4998(200102)57:2<165::AID-PS289>3.0.CO;2-G.
- K.P. Yáñez, J.L. Bernal, M.J. Nozal, M.T. Martín and J. Bernal, J. Chromatogr. A, 1285, 110 (2013); doi:10.1016/j.chroma.2013.02.032.
- Y. Hao, S. Ke and Z. Min-heng, Nong Yao, 51, 850 (2012).
- H.-J. Kim, S. Liu, Y.-S. Keum and Q.X. Li, J. Agric. Food Chem., 51, 1823 (2003); doi:10.1021/jf0210472.
- Z. Chou, C. Shao-Ting and C. Zhu-Wei, Chem. Ind., 37, 24 (2006).
- S. Jian, Y. Shi-Feng and P. Feng-Mei, J. Qingdao Agric. Univ. (Nat. Sci.), 24, 310 (2007).
- T. Xian-Jian, Xian Dai Nong Yao, 5, 11 (2006).
- F.H. Allen, O. Kennard, D.G. Watson, L. Brammer, A.G. Orpen and R. Taylor, J. Chem. Soc., Perkin Trans. 2, S1 (1987); doi:10.1039/p298700000s1.
- J. Folkman, Sci. Am., 275, 150 (1996); doi:10.1038/scientificamerican0996-150.
- A.C.T. North, D.C. Phillips and F.S. Mathews, Acta Crystallogr. A, 24, 351 (1968); doi:10.1107/S0567739468000707.
- G.M. Sheldrick, Acta Crystallogr. A, 64, 112 (2008); doi:10.1107/S0108767307043930.
References
S. Al Zadjali, S. Morse, J. Chenoweth and M. Deadman, Sci. Total Environ., 476-477, 505 (2014); doi:10.1016/j.scitotenv.2013.12.040.
J. Patil, J. Ashoka, M. Bheemanna and K. Narayana, J. Entomol. Res., 37, 207 (2013).
Z. Yi-xuan and Z. Yi-bin, Shi Jie Nong Yao, 35, 23 (2013).
P. Maienfisch, H. Huerlimann, A. Rindlisbacher, L. Gsell, H. Dettwiler, J. Haettenschwiler, E. Sieger and M. Walti, Pest Manage. Sci., 57, 165 (2001); doi:10.1002/1526-4998(200102)57:2<165::AID-PS289>3.0.CO;2-G.
K.P. Yáñez, J.L. Bernal, M.J. Nozal, M.T. Martín and J. Bernal, J. Chromatogr. A, 1285, 110 (2013); doi:10.1016/j.chroma.2013.02.032.
Y. Hao, S. Ke and Z. Min-heng, Nong Yao, 51, 850 (2012).
H.-J. Kim, S. Liu, Y.-S. Keum and Q.X. Li, J. Agric. Food Chem., 51, 1823 (2003); doi:10.1021/jf0210472.
Z. Chou, C. Shao-Ting and C. Zhu-Wei, Chem. Ind., 37, 24 (2006).
S. Jian, Y. Shi-Feng and P. Feng-Mei, J. Qingdao Agric. Univ. (Nat. Sci.), 24, 310 (2007).
T. Xian-Jian, Xian Dai Nong Yao, 5, 11 (2006).
F.H. Allen, O. Kennard, D.G. Watson, L. Brammer, A.G. Orpen and R. Taylor, J. Chem. Soc., Perkin Trans. 2, S1 (1987); doi:10.1039/p298700000s1.
J. Folkman, Sci. Am., 275, 150 (1996); doi:10.1038/scientificamerican0996-150.
A.C.T. North, D.C. Phillips and F.S. Mathews, Acta Crystallogr. A, 24, 351 (1968); doi:10.1107/S0567739468000707.
G.M. Sheldrick, Acta Crystallogr. A, 64, 112 (2008); doi:10.1107/S0108767307043930.