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Synthesis and Antifungal Activities of Novel Fluorine-Containing Triazole Compounds
Corresponding Author(s) : Zhi-Wei Zhai
Asian Journal of Chemistry,
Vol. 27 No. 1 (2015): Vol 27 Issue 1
Abstract
A series of novel triazole compounds containing fluorinated arylphenyl ether group were designed and synthesized. Al1 the new compounds were identified by IR, 1H NMR and elemental analysis. Their in vitro antifungal activities against five common pathogens were evaluated by mycelial growth rate method. The preliminary bioassay indicated that all the target compounds possess some fungicidal activities against Gibberella zeae, Alternaria solani, Fusarium oxysporum, Physalospora pircola and Cercospora arachidicola. In particular, compound 5e exhibited excellent antifungal activities, its inhibition rates against all selective tested pathogens reached more than 90 % at 50 μg/mL.
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- K. Shiokawa, S. Tsuboi, S. Kagabu and K. Moriya, EP 192060 (1986).
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References
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L.Z. Xu, Y.W. Huang, G.P. Yu, G.D. Si and Q. Zhu, Struct. Chem., 17, 235 (2006); doi:10.1007/s11224-006-9050-0.
G.L. Almajan, S.F. Barbuceanu, G. Bancescu, I. Saramet, G. Saramet and C. Draghici, Eur. J. Med. Chem., 45, 6139 (2010); doi:10.1016/j.ejmech.2010.10.007.
X.H. Sun, Y. Bai, Y.F. Liu, B. Chen and Y.Q. Jia, Chem. J. Chinese Univ., 32, 1312 (2011).
Y.M. Sun, F.Y. Dong, Z.H. Li, Q. Yang and F.S. Su, Chinese Agric. Sci. Bull., 28, 257 (2012).
J.H. Parsons and P.J. West, Pesticidal 1,2,4-Triazole Compounds, U.S. Patent 4414221 (1981).
Y.M. Ma, R.H. Liu, X.Y. Gong, Z. Li, Q.C. Huang, H.S. Wang and G.H. Song, J. Agric. Food Chem., 54, 7724 (2006); doi:10.1021/jf0609328.
D. Mares, C. Romagnoli, E. Andreotti, M. Manfrini and C.B. Vicentini, J. Agric. Food Chem., 52, 2003 (2004); doi:10.1021/jf030695y.
Y.P. Hou, J. Sun, Z.H. Pang, P.-C. Lv, D.-D. Li, L. Yan, H.-J. Zhang, E.X. Zheng, J. Zhao and H.-L. Zhu, Bioorg. Med. Chem., 19, 5948 (2011); doi:10.1016/j.bmc.2011.08.063.
G.R. Jadhav, M.U. Shaikh, R.P. Kale, M.R. Shiradkar and C.H. Gill, Eur. J. Med. Chem., 44, 2930 (2009); doi:10.1016/j.ejmech.2008.12.001.
N.B. Patel, I.H. Khan and S.D. Rajani, Eur. J. Med. Chem., 45, 4293 (2010); doi:10.1016/j.ejmech.2010.06.031.
H.Y. Mao, H. Song and D.Q. Shi, J. Heterocycl. Chem., 49, 511 (2012); doi:10.1002/jhet.783.
G. Klopman and D. Ptchelintsev, J. Comput. Aided Mol. Des., 7, 349 (1993); doi:10.1007/BF00125508.
P.A. Worthington, Pestic. Sci., 31, 457 (1991); doi:10.1002/ps.2780310405.
S. Reinhard, Zesz. Probl. Postepow Nauk Roln, 371, 33 (1988).
16 K. Sztanke, T. Tuzimski, J. Rzymowska, K. Pasternak and M. Kandefer-Szerszeń, Eur. J. Med. Chem., 43, 404 (2008); doi:10.1016/j.ejmech.2007.03.033.
A. Hubele and P. Riebli, U.S. Patent 5266585 (1993).
A. Hubele and P. Riebli, GB 2098607 (1982).
T. Billard and B.R. Langlois, J. Org. Chem., 67, 997 (2002); doi:10.1021/jo016265t.
G. Meazza, F. Rama, F. Bettarini, P. Piccardi, P. Massardo and V. Caprioli, Pestic. Sci., 35, 137 (1992); doi:10.1002/ps.2780350207.
F. Rama, G. Meazza, F. Bettarini, P. Piccardi, P. Massardo and V. Caprioli, Pestic. Sci., 35, 145 (1992); doi:10.1002/ps.2780350208.
X.H. Qian, X.Y. Xu, Z.B. Li, Z. Li and G.H. Song, J. Fluor. Chem., 125, 1609 (2004); doi:10.1016/j.jfluchem.2004.09.002.
X.H. Qian, Z. Liu, Z.B. Li, Z. Li and G.H. Song, J. Agric. Food Chem., 49, 5279 (2001); doi:10.1021/jf010632k.
K. Shiokawa, S. Tsuboi, S. Kagabu and K. Moriya, EP 192060 (1986).
E.P. Kohler and H.M. Chadwell, Org. Synth., 2, 1 (1922); doi:10.15227/orgsyn.002.0001.
R.M. Cowper and L.H. Davidson, Org. Synth. Collect., 2, 480 (1943).
C.Q. Sheng, Y. Chen, W.N. Zhang and Y.L. Song, Chin. J. Med Chem., 12, 344 (2002).
J.X. Wang, West China J. Pharm. Sci., 20, 241 (2005).
Y. Wang, A.X. Hu, P. Chen and M. Chen, Agrochemicals, 45, 397 (2006).
J.L. Sun and W. Mu, Pesticide Science Experimental Techniques and Guidance; Chemical Industry Press: Beijing, China, p. 228 (2009).