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Synthesis, Crystal Structure and Biological Activity of 4-Cyclopropyl-3-[(3-fluorobenzyl)thio]-5-methyl-4H-1,2,4-triazole Monohydrate
Corresponding Author(s) : Hong-Ke Wu
Asian Journal of Chemistry,
Vol. 25 No. 15 (2013): Vol 25 Issue 15
Abstract
The compound 4-cyclopropyl-3-[(3-fluorobenzyl)thio]-5-methyl-4H-1,2,4-triazole monohydrate (C13H14N3SF·H2O) were synthesized and recrystallized from ethanol. The compound was characterized by 1H NMR, elemental analyses and X-ray diffraction. The compound crystallized in the orthorhombic space group Pbca with a = 10.513(2), b = 8.4646(17), c = 30.965(6) Å, a = 90, b = 90, g =90º, V = 2755.6(10) Å3, Z = 8 and R = 0.0510 for 2542 observed reflections with I > 2s(I). X-ray analysis reveals that not only intermolecular O–H···N interactions, but also C-H···p stacking interactions exist in the adjacent molecules. The biological activities results showed that it exhibited significant herbicidal activity against Brassica napus.
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- (a) X.H. Liu, C.X. Tan and J.Q. Weng, Asian J. Chem., 23, 4064 (2011); (b) X.H. Liu, C.X. Tan and J.Q. Weng, Phosphorus Sulfur Silicon Rel. Elem., 186, 552 (2011); (c) J.Y. Dong, X.L. Feng and Z.H. Zhang, Asian J. Chem., 24, 5286 (2012); (d) J.Y. Tong, Y.X. Shi, X.H. Liu, N.B. Sun and B.J. Li, Chin. J. Org. Chem., 32, 2373 (2012); (e) X.H. Liu, W.G. Zhao, B.L. Wang and Z.M. Li, Res. Chem. Intermed., 38, 1999 (2012); (f). N.B. Sun, J.Z. Jin, C. Lei and W. Ke, Asian J. Chem., 25, 4067 (2013).
- (a) Y.L. Xue, Y.G. Zhang and X.H. Liu, Asian J. Chem., 24, 3016 (2012); (b) P.Q. Chen, C.X. Tan, J.Q. Weng and X.H. Liu, Asian J. Chem., 24, 2808 (2012); (c) Y.L. Xue, Y.G. Zhang and X.H. Liu, Asian J. Chem., 24, 1571 (2012); (d) Y.L. Xue, Y.G. Zhang and X.H. Liu, Asian J. Chem., 24, 5087 (2012).
- (a) R.J.R. Rao,A.K.S.B. Rao, K. Swapna, B.B. Rani and Y.L.N. Murthy, Asian J. Chem., 24, 1837 (2012); (b) S.A. Zabin, Asian J. Chem., 23, 4067 (2011); (c) F.M. A. Altalbawy and E.S.S. Darwish, Asian J. Chem., 23, 2951 (2011); (d) J. Salimon, N. Salih, H. Ibraheem and E. Yousif, Asian J. Chem., 22, 5289 (2010); (e) R.J. Singh and D.K. Singh, Asian J. Chem., 22, 2659 (2010).
- (a) A. Hasan, M.N. Akhtar and S. Gapil, Asian J. Chem., 24, 1837 (2012); (b) W. Chen, F. Xiang, J. Fu, Q.F. Zeng and H.L. Zhu, Asian J. Chem., 23, 602 (2011); (c) F.M.A. Altalbawy, G.G. Mohamed and M.I.A. Mohamed, Asian J. Chem., 22, 7291 (2010).
- Z.Y. Li, Y. Cao, P. Zhan, C. Pannecouque, J. Balzarini, E. De Clercq and X.Y. Liu, Lett. Drug Des. Discov., 10, 27 (2013).
- S. Baytas, E. Kapcak, T. Coban and H. Ozbilge, Turkish J. Chem., 36, 867 (2012).
- R.J. Singh and D.K. Singh, Asian J. Chem., 22, 2664 (2010).
- (a) X.H. Liu, J.Q. Weng, C.X. Tan, L. Pan, B.L. Wang and Z.M. Li, Asian J. Chem., 23, 4031 (2011); (b) X.H. Liu, P.Q. Chen, B.L. Wang, Y.H. Li, S.H. Wang and Z.M. Li, Bioorg. Med. Chem. Lett., 17, 3784 (2007).
- X.H. Liu, P.Q. Chen, B.L. Wang, W.L. Dong, Y.H. Li, X.Q. Xie and Z.M. Li, Chem. Biol. Drug Des., 75, 228 (2010).
- B.C. Gerwick, L.C. Mireles and R.J. Eilers, Weed Technol., 7, 519 (1993).
- G.M. Sheldrick, SHELXS97 and SHELXL97, University of Göttingen, Germany (1997).
- Wilson, A. J. International Table for X-ray Crystallograghy, Vol C, Kluwer Academic Publisher, Dordrecht, 1992, Tables 6.1.1.4 (500) and 4.2.6.8 (219)
References
(a) X.H. Liu, C.X. Tan and J.Q. Weng, Asian J. Chem., 23, 4064 (2011); (b) X.H. Liu, C.X. Tan and J.Q. Weng, Phosphorus Sulfur Silicon Rel. Elem., 186, 552 (2011); (c) J.Y. Dong, X.L. Feng and Z.H. Zhang, Asian J. Chem., 24, 5286 (2012); (d) J.Y. Tong, Y.X. Shi, X.H. Liu, N.B. Sun and B.J. Li, Chin. J. Org. Chem., 32, 2373 (2012); (e) X.H. Liu, W.G. Zhao, B.L. Wang and Z.M. Li, Res. Chem. Intermed., 38, 1999 (2012); (f). N.B. Sun, J.Z. Jin, C. Lei and W. Ke, Asian J. Chem., 25, 4067 (2013).
(a) Y.L. Xue, Y.G. Zhang and X.H. Liu, Asian J. Chem., 24, 3016 (2012); (b) P.Q. Chen, C.X. Tan, J.Q. Weng and X.H. Liu, Asian J. Chem., 24, 2808 (2012); (c) Y.L. Xue, Y.G. Zhang and X.H. Liu, Asian J. Chem., 24, 1571 (2012); (d) Y.L. Xue, Y.G. Zhang and X.H. Liu, Asian J. Chem., 24, 5087 (2012).
(a) R.J.R. Rao,A.K.S.B. Rao, K. Swapna, B.B. Rani and Y.L.N. Murthy, Asian J. Chem., 24, 1837 (2012); (b) S.A. Zabin, Asian J. Chem., 23, 4067 (2011); (c) F.M. A. Altalbawy and E.S.S. Darwish, Asian J. Chem., 23, 2951 (2011); (d) J. Salimon, N. Salih, H. Ibraheem and E. Yousif, Asian J. Chem., 22, 5289 (2010); (e) R.J. Singh and D.K. Singh, Asian J. Chem., 22, 2659 (2010).
(a) A. Hasan, M.N. Akhtar and S. Gapil, Asian J. Chem., 24, 1837 (2012); (b) W. Chen, F. Xiang, J. Fu, Q.F. Zeng and H.L. Zhu, Asian J. Chem., 23, 602 (2011); (c) F.M.A. Altalbawy, G.G. Mohamed and M.I.A. Mohamed, Asian J. Chem., 22, 7291 (2010).
Z.Y. Li, Y. Cao, P. Zhan, C. Pannecouque, J. Balzarini, E. De Clercq and X.Y. Liu, Lett. Drug Des. Discov., 10, 27 (2013).
S. Baytas, E. Kapcak, T. Coban and H. Ozbilge, Turkish J. Chem., 36, 867 (2012).
R.J. Singh and D.K. Singh, Asian J. Chem., 22, 2664 (2010).
(a) X.H. Liu, J.Q. Weng, C.X. Tan, L. Pan, B.L. Wang and Z.M. Li, Asian J. Chem., 23, 4031 (2011); (b) X.H. Liu, P.Q. Chen, B.L. Wang, Y.H. Li, S.H. Wang and Z.M. Li, Bioorg. Med. Chem. Lett., 17, 3784 (2007).
X.H. Liu, P.Q. Chen, B.L. Wang, W.L. Dong, Y.H. Li, X.Q. Xie and Z.M. Li, Chem. Biol. Drug Des., 75, 228 (2010).
B.C. Gerwick, L.C. Mireles and R.J. Eilers, Weed Technol., 7, 519 (1993).
G.M. Sheldrick, SHELXS97 and SHELXL97, University of Göttingen, Germany (1997).
Wilson, A. J. International Table for X-ray Crystallograghy, Vol C, Kluwer Academic Publisher, Dordrecht, 1992, Tables 6.1.1.4 (500) and 4.2.6.8 (219)