Browse > Article
http://dx.doi.org/10.5012/bkcs.2012.33.8.2627

Design, Synthesis and Antifungal Activities of Novel Strobilurin Derivatives Containing Pyrimidine Moieties  

Zhang, Xiang (Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences)
Gao, Yong-Xin (Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences)
Liu, Hui-Jun (Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences)
Guo, Bao-Yuan (Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences)
Wang, Hui-Li (Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences)
Publication Information
Bulletin of the Korean Chemical Society / v.33, no.8, 2012 , pp. 2627-2634 More about this Journal
Abstract
Strobilurins are one of the most important classes of agricultural fungicides. To discover new strobilurin derivatives with high activity against resistant pathogens, a series of novel ${\beta}$-methoxyacrylate analogues were designed and synthesized by integrating substituted pyrimidine with a strobilurin pharmacophore. The compounds were confirmed and characterized by infrared, $^1H$ nuclear magnetic resonance, elemental analysis and mass spectroscopy. The bioassays indicated that most of the compounds (1a-1h) exhibited potent antifungal activities against Colletotrichum orbiculare, Botrytis cinerea Pers and Phytophthora capsici Leonian at the concentration of 50 ${\mu}g/mL$. Exhilaratingly, compound 1d (R=3-trifluoromethylphenyl) showed better antifungal activity against all the tested fungi than the commercial strobilurin fungicide azoxystrobin.
Keywords
Synthesis; Strobilurin derivatives; Antifungal activities; Pyrimidine;
Citations & Related Records
Times Cited By KSCI : 1  (Citation Analysis)
Times Cited By Web Of Science : 0  (Related Records In Web of Science)
연도 인용수 순위
1 Clough, J. M.; Godfrey Christopher, R. A.; Streeting, I. T.; Cheetham, R. EP 0382375, 1990.
2 Sauter, H.; Steglich, W.; Anke, T. Angew. Chem. Int. Ed. 1999, 38, 1328.   DOI   ScienceOn
3 Kim J. H.; Chan, K. L.; Mahoney, N.; Campbell, B. C. Ann. Clin. Microbiol. Antimicrob. 2011, 10, 23.   DOI
4 Li, M.; Liu, C. L.; Li, L.; Yang, H.; Li, Z. N.; Zhang, H. Pest Manag. Sci. 2010, 66, 107.   DOI
5 Li, Y. H.; Liu, R.; Yan, Z. W.; Zhang, X. N.; Zhu, H. J. Bull. Korean Chem. Soc. 2010, 31, 3341.   DOI   ScienceOn
6 Nagata, T.; Masuda, K.; Maeno, S.; Miura, I. Pest Manage. Sci. 2004, 60, 399.   DOI
7 Rune, R.; Eva, A.; Jonas, U.; Thomas, L.; Lena, R.; Tjeerd, B. Bioorg. Med. Chem. Lett. 2004, 14, 4449.   DOI
8 Suzuki, K.; Okawara, T.; Higashijima, T.; Yokomizo, K.; Mizushima, T.; Otsuka, M. Bioorg. Med. Chem. Lett. 2005, 15, 2065.   DOI
9 Mai, A.; Artico, M.; Rotili, D.; Tarantino, D.; Clotet-Codina, I.; Armand-Ugón, M.; Ragno, R.; Simeoni, S.; Sbardella, G.; Nawrozkij, M. B.; Samuele, A.; Maga, G.; Est, J. J. Med. Chem. 2007, 50, 5412.   DOI
10 Li, H. C.; Liu, C. L.; Chai, B. S.; Li, M.; Li, Z. N.; Yang, J. C. Nat. Prod. Commun. 2009, 4, 1209.
11 Li, H. C.; Chai, B. S.; Li, Z. N.; Yang, J. C.; Liu, C. L. Chin. Chem. Lett. 2009, 20, 1287.   DOI
12 Li, M.; Liu, C. L.; Yang, J. C.; Zhang, J. B.; Li, Z. N.; Zhang, H. J. Agric. Food Chem. 2010, 58, 2664.   DOI
13 Chai, B. S.; Liu, C. L.; Li, H. C.; He, X. M.; Luo, Y. M.; Huang, G.; Zhang, H.; Chang, J. B. Pest Manag. Sci. 2010, 66, 1208.   DOI
14 Jones, J. D.; DeBoos, G. A.; Wilkinson, P.; Cox, B. G.; Fielden, J. M. US Patent 5760250, 1998.
15 Chuan, Y. M.; Wang, C.; Peng, Y. G. Chin. J. Synth. Chem. 2007, 15, 798.
16 Huchel, U.; Schmidt, C.; Schmidt, R. Tetrahedron Lett. 1995, 36, 9457.   DOI
17 David, D. D.; Gary, B. P. US Patent 6372751 B1, 2002.
18 Castelhano, A.; McKibben, B.; Steinig, A.; Collington, E. US Patent 162764 A1, 2003.
19 Inoue, K.; Tsurumi, T.; Ishii, H.; Park, P.; Ikeda, K. FEMS Microbiol Lett. 2012, 326, 83.   DOI
20 Bartlett, D. W.; Clough, J. M.; Godwin, J. R.; Hall, A. A.; Hamer, M.; Parr-Dobrzanski, B. Pestic. Manage. Sci. 2002, 58, 649.   DOI   ScienceOn
21 Beautement, K.; Clough, J. M.; de Fraine, P. J.; Godfrey, C. R. A. Pestic. Sci. 1991, 31, 499.   DOI   ScienceOn
22 Zhao, P. L.; Wang, L.; Zhu, X. L.; Huang, X. Q.; Zhan, C. G.; Wu, J. W.; Yang, G. F. J. Am. Chem. Soc. 2010, 132, 185.   DOI
23 Zhao, P. L.; Wang, F.; Zhang, M. Z.; Liu, Z. M.; Huang, W.; Yang, G. F. J. Agric. Food Chem. 2008, 56, 10767.   DOI   ScienceOn
24 Zhao, P. L.; Liu, C. L.; Huang, W.; Wang, Y. Z.; Yang, G. F. J. Agric. Food Chem. 2007, 55, 5697.   DOI   ScienceOn
25 Huang, W.; Zhao, P. L.; Liu, C. L.; Chen, Q.; Liu, Z. M.; Yang, G. F. J. Agric. Food Chem. 2007, 55, 3004.   DOI   ScienceOn
26 Gisi, U.; Sierotzki, H.; Cook, A.; McCaffery, A. Pest Manage. Sci. 2002, 58, 859.   DOI
27 Iwata, S.; Lee, J. W.; Okada, K.; Lee, J. K.; Iwata, M.; Rasmussen, B.; Link, T. A.; Ramaswamy, S.; Jap, B. K. Science 1998, 281, 64.   DOI
28 Becker, W. F.; Jagow, V. G.; Anke, T.; Steglich, W. FEBS Lett. 1981, 132, 329.   DOI
29 Luo, Y. P.; Li, Y. X.; Zhao, P. L.; Huang, W.; Yang, G. F. Sci. China 2006, 1, 20.
30 Fisher, N.; Meunier, B. Pestic. Manage. Sci. 2005, 61, 973.   DOI
31 Li, Y.; Liu, J.; Zhang, H. Q.; Yang, X. P.; Liu, Z. J. Bioorg. Med. Chem. Lett. 2006, 16, 2278.   DOI
32 Li, Y.; Zhang, H. Q.; Liu, J.; Yang, X. P.; Liu, Z. J. J. Agric. Food Chem. 2006, 54, 3636.   DOI
33 Chen, H.; Taylor, J. L.; Abrams, S. R. Bioorg. Med. Chem. Lett. 2007, 17, 1979.   DOI
34 Anke, T.; Oberwinkler, F.; Steglich, W.; Schramm, G. J. Antibiot. 1977, 30, 806.   DOI
35 Aspinall, I. H.; Worthington, P. A. Pestic. Sci. 1999, 55, 197.