Browse > Article
http://dx.doi.org/10.5012/bkcs.2010.31.11.3341

Synthesis, Crystal Structure and Fungicidal Activities of New Type Oxazolidinone-Based Strobilurin Analogues  

Li, Yuhao (Department of Applied Chemistry, College of Science, Nanjing University of Technology)
Liu, Rui (Department of Applied Chemistry, College of Science, Nanjing University of Technology)
Yan, Zhangwei (Department of Applied Chemistry, College of Science, Nanjing University of Technology)
Zhang, Xiangning (Jiangsu Pesticide Research Institute Co. Ltd.)
Zhu, Hongjun (Department of Applied Chemistry, College of Science, Nanjing University of Technology)
Publication Information
Abstract
A series of oxazolidinone-based strobilurin analogues were efficiently synthesized by the reaction of 3-(2-bromomethylphenyl) oxazolidin-2-one with 1-substituted phenyl-2H-pyrazolin-3-one. Their structures were confirmed and characterized by $^1H$-NMR, $^{13}C$-NMR, elemental analysis, and mass spectroscopy. In addition, the crystal structure of the target compound 3-(2-((1-phenyl-2H-pyrazol-3-yloxy)methyl)phenyl) oxazolidin-2-one was determined by single crystal X-ray diffraction. The bioassay results of these compounds indicated that some of the oxazolidin-2-one derivatives containing N-substituted phenyl 2H-pyrazol ring exhibited potential in vivo fungicidal activities against M. grisea at the dosage of $1\;g\;L^{-1}$.
Keywords
Strobilurin fungicide; Oxazolidinone; Synthesis; X-ray diffraction; Structure-activity relationships;
Citations & Related Records
Times Cited By KSCI : 1  (Citation Analysis)
Times Cited By Web Of Science : 2  (Related Records In Web of Science)
Times Cited By SCOPUS : 6
연도 인용수 순위
1 Michael, E.; Augustyniak, E. D.; Cochran, J. L. E.; Fang, X. Q.; David, S. G.; David, R. J. J. Med. Chem. 2007, 50, 6367.   DOI   ScienceOn
2 Koenig, H.; Goetz, N.; Klein, U.; Eller, K. WO 9703969, 1997.
3 Fancher, L. W.; Gless, R. D. Tetrahedron Lett. 1988, 29, 5095.   DOI   ScienceOn
4 Morita, Y.; Ishigaki, T.; Kawamura, K.; Iseki, K. Synthesis 2007, 16, 2517.
5 Gurdere, M. B.; Budak, Y.; Ceylan, M. Asian J. Chem. 2008, 20, 1425.
6 Martins, A. M.; Rory, N. G. S.; Jose, N. R. J.; Antonio, E. J.; Alicia G. B.; Antonio, R. M. F.; Vicente, J. A. ChemMedChem. 2009, 4, 78.   DOI   ScienceOn
7 Sheldrick, G. M. SHELXL-97, Program for the Refinement of Crystal Structures, University of Gottingen, 1997.
8 Jarosław, W.; Ewa, K.; Janusz, J. S.; Zbigniew, J. B. Pest Manag. Sci. 2001, 57, 625.   DOI   ScienceOn
9 Huang, W.; Zhao, P.-L.; Liu, G.-L.; Chen, Q.; Liu, Z.-M.; Yang, G.-f. J. Agric. Food Chem. 2007, 55, 3004.   DOI   ScienceOn
10 Mueller, B.; Koenig, H.; Kirstgen, R.; Oberdorf, K.; Roehl, F.; Goetz, N.; Sauter, H.; Lorenz, G.; Ammermann, E. DE 4423612 1996.
11 Li, Y.; Zhang, H.-Q.; Liu, J.; Yang, X.-P.; Liu, Z.-J. J. Agric. Food Chem. 2006, 54, 3636.   DOI   ScienceOn
12 Zhao, P.-L.; Liu, G.-L.; Huang, W.; Wang, Y.-Z.; Yang, G.-F. J. Agric. Food Chem. 2007, 55, 5697.   DOI   ScienceOn
13 Liu, A.-P.; Wang, X.-G.; Ou, X.-M.; Huang, Z.-M.; Chen, C.; Liu, S.-D.; Huang, L.; Liu, X.-P.; Zhang, C.-L.; Zheng, Y.-Q.; Ren, Y.-G.; He, L.; Yao, J.-R. J. Agric. Food Chem. 2008, 56, 6562.   DOI   ScienceOn
14 Tu, S.; Xu, L. H.; Ye, L.-L.; Wang, X.; Sha, Y.; Xiao, Z.-Y. J. Agric. Food Chem. 2008, 56, 5247.   DOI   ScienceOn
15 Hwang, I.-C.; Kim, J.-K.; Kim, H.-H.; Kyung, S.-H. Bull. Korean Chem. Soc. 2009, 30, 1475.   과학기술학회마을   DOI   ScienceOn
16 Stefan, H.; Kai, S.; Harald, K.; Uwe, C. Plant Physiol. 2002, 130, 120.   DOI   ScienceOn
17 Josep, V. M.; Celia, S. P.; Consuelo, A.; Antonio, A.; Antonio, A. F. J. Agric. Food Chem. 2008, 56, 7682.   DOI   ScienceOn
18 Zhang, Z.-L.; Huang, L.; Shulmeister, V. M.; Chi, Y.; Kim, K. K.; Hung, L. W.; Croftsk, A. R.; Berry, E. A.; Kim, S. H. Science 1998, 281, 64.   DOI   ScienceOn
19 Ulrich, G.; Helge, S.; Alison, C.; Alan, M. Pest Manag. Science 2002, 58, 859.
20 Zappia, G.; Menendez, P.; Delle, M. G.; Misiti, D.; Nevola, L.; Botta, B. Mini-Rev. Med. Chem. 2007, 7, 389.   DOI   ScienceOn
21 Zappia, G.; Cancelliere, G.; Gacs, B. E.; Delle, M. G.; Misiti, D.; Nevola, L.; Botta, B. Curr. Org. Syn. 2007, 4, 238.   DOI   ScienceOn
22 Renslo, A. R.; Luehr, G. W.; Gordeev, M. F. Bioorg. Med. Chem. 2006, 14, 4227.   DOI   ScienceOn
23 Mukhtar, T. A.; Wright, G. D. Chem. Rev. 2002, 105, 529.   DOI   ScienceOn
24 Wenderoth, B.; Rentzea, C.; Ammermann, E.; Pommer, E. H.; Steglich, W.; Anke, T. DE 3623921 1988.
25 Takase, A.; Kai, H.; Nishida, K.; Masui, M. EP 535928 1993.
26 Heinemann, U.; Gayer, H.; Gerdes, P.; Krueger, B. W.; Gallenkamp, B.; Stelzer, U.; Marhold, A.; Tiemann, R.; Stefan, D.; Gerd, H.; Stenzel, K. DE 19602095 1997.