Articles

Synthesis and Fungicidal Activities of Nucleoside Compounds Containing Substituted Benzoyl Thiourea

  • Miao Hongjian ,
  • Zhang Jiwei ,
  • Yuan Huizhu ,
  • Li Ying ,
  • Xu Yan ,
  • Li Hui ,
  • Yang Xinling ,
  • Ling Yun
Expand
  • a Key Laboratory of Pesticide Chemistry and Application, Ministry of Agriculture, Department of Applied Chemistry,College of Science, China Agricultural University, Beijing 100193;
    b Institute of Plant Protection, Chinese Academy of Agricultural Sciences, Beijing 100193

Received date: 2011-10-11

  Revised date: 2011-11-26

  Online published: 2012-01-10

Supported by

Project supported by the National Natural Science Foundation of China (No. 21072222), the National Basic Research Program of China (973 Program) (No. 2010CB126104), and the National “Twelfth Five-Year” Plan for Science & Technology Support (No. 2011BAE06B05-5).

Abstract

To find new fungicidal lead compounds, based on the catalytic mechanism of chitin synthase, a series of novel nucleoside compounds containing thiourea were designed via the method of linking active sub-structures, in which the thiourea with high fungicidal activity was combined to the uridine part of polyoxins and nikkomycins. The target compounds were synthesized from uridine in 5 steps. Their structures were confirmed by IR, 1H NMR spectra and elemental analysis. The preliminary bioassay results indicated that some compounds showed obvious inhibition effects against Phomopsisasparagi bubak, especially, and the fungicidal activity of 6m (97.2%) at 50 μg/mL is similar to that (100%) of polyoxin B.

Cite this article

Miao Hongjian , Zhang Jiwei , Yuan Huizhu , Li Ying , Xu Yan , Li Hui , Yang Xinling , Ling Yun . Synthesis and Fungicidal Activities of Nucleoside Compounds Containing Substituted Benzoyl Thiourea[J]. Chinese Journal of Organic Chemistry, 2012 , 32(05) : 915 -921 . DOI: 10.6023/cjoc1110111

References

[1] Gooday, G. W. In The Biochemistry of Cell Walls and Membranes inFungi, Eds.: Goosey, M.; Kuhn, P.; Trinci, A. P., Springer-Verlag,Berlin, 1989, pp. 61~76.  

[2] Grosscurt, A. C.; Tipker, J. Pestic. Biochem. Physiol. 1980, 13, 249.  

[3] (a) Isono, K.; Nagatsu, J.; Kawashiwa, Y.; Suzuki, S. Agric. Biol.Chem. 1965, 29, 848.(b) Isono, K.; Asahi, K.; Suzuki, S. J. Am. Chem. Soc. 1969, 91,7490.(c) Isono, K.; Suzuki, S. Heterocycles 1979, 13, 333.  

[4] (a) Dähn, J.; Hagenmaier, H.; Höhner, H.; König, W. A.; Wolf, G.;Zähner, H. Arch. Microbiol. 1976, 107, 143.(b) Hagenmaier, H.; Keckeisen, A.; Zähner, H.; König, W. A. LiebigsAnn. Chem. 1979, 10, 1494.(c) König, W. A.; Hass, W.; Dehler, W.; Fiedler, H. P.; Zähner, H.Liebigs Ann. Chem. 1980, 4, 622.

[5] Khare, R. K.; Becker, J. M.; Naider, F. R. J. Med. Chem. 1988, 31,650.  

[6] Ephraim, C. Pest Manage. Sci. 2001, 57, 946.  

[7] (a) Hori, M.; Misato, T. Agric. Biol. Chem. 1974, 38, 691.(b) Hori, M.; Misato, T. Agric. Biol. Chem. 1974, 38, 699.(c) Wang, R.; Steensma, D. H.; Takaoka, Y.; Yun, J. W.; KaJimoto,T.; Wong, C. H. Bioorg. Med. Chem. 1997, 237, 476.

[8] Obi, K.; Uda, J.; Matsuda, A. Bioorg. Med. Chem. Lett. 2000, 10,1451.  

[9] Preeti, M. C.; Sunita, R. D. Bioorg. Med. Chem. 2009, 17, 2433.  

[10] (a) Li, Y.; Li, B.-J.; Ling, Y.; Miao, H.-J.; Yang, X.-L. J. Agric.Food Chem. 2010, 58, 3037.(b) Li, Y.; Li, B.-J.; Ling, Y.; Miao, H.-J.; Yang, X.-L. Chin. J. Org.Chem. 2011, 31, 1411 (in Chinese).(李映, 李宝聚, 凌云, 苗宏健, 杨新玲, 有机化学, 2011, 31,1411.)

[11] (a) Krishnamurthy, R. Pestic. Sci. 1998, 52, 145.(b) Julio, J. C. J. Inorg. Biochem. 2005, 99, 1558.(c) Zhou, W.-Q. Ph.D Dissertation, Nanjing University of Scienceand Technology, Nanjing, 2004 (in Chinese).(周为群, 博士论文, 南京理工大学, 南京, 2004.)  

[12] Andrej, B.; Stanislav, G. Tetrahedron 2008, 64, 9093.  

[13] Zhang, Z.-W. J. Central China Normal Univ. (Nat. Sci. ) 2007, 41,88 (in Chinese).(张正文, 华中师范大学学报(自然科学版), 2007, 41, 88. )

[14] Chen, N.-C. Bioassay of Pesticides, Beijing Agricultural UniversityPress, Beijing, 1991, p. 161 (in Chinese).(陈年春, 农药生物测定技术, 北京农业大学出版社, 北京,1991, p. 161.)
Outlines

/