Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Minimum Structural Requirements for Fungicidal Evaluation of N-Phenyl-O-phenylthionocarbamates against the Capsicum Phytophthora Blight (Phyophthora capsici) Based on the 3D-QSARs

  • Soung, Min-Gyu (Department of Applied Biology and Chemistry, College of Agriculture and Life Science, Chungnam National University) ;
  • Jang, Seok-Chan (Department of Applied Biology and Chemistry, College of Agriculture and Life Science, Chungnam National University) ;
  • Sung, Nack-Do (Department of Applied Biology and Chemistry, College of Agriculture and Life Science, Chungnam National University)
  • Received : 2010.03.23
  • Accepted : 2010.09.15
  • Published : 2010.11.20
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Abstract

In this study, the 3D-QSARs (three-dimensional quantitative structure-activity relationships: CoMFA and CoMSIA) between structural changes of N-phenyl-O-phenylthionocarbamate analogues (1-30) and their fungicidal activities against the capsicum phytophthora (Phyophthora capsici) fungi were analyzed, then considered quantitatively in terms of minimum structural requirements for fungicidal evaluation. The statistical qualities ($r^2_{cv.}$ = 0.510 and $r^2_{ncv.}$ = 0.948) of the optimal CoMFA 1 model are improved over the other models in the conditions of field combinations, and the two alignments. In the optimal CoMFA 1 model, relative contribution percentages of the CoMFA field were: steric field, 52.3%; electrostatic field, 37.8%; hydrophobic field, 9.9%. Results were similar for the CoMFA 2 model. Therefore, the steric field of the analogues had the highest contribution ratio for fungicidal activity. Specifically, with the contour map of steric fields, the fungicidal activity increased when bulky steric Y-substituents were introduced to the meta-position on the N-phenyl ring and small steric Y-subsituents were introduced to its para-position.

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References

  1. Hutson, D. H.; Roberts, T. R. Insecticides, In Progress in Pesticide Biochemistry and Toxicology; Wiley: Chichester, 1987; Vol. 5.
  2. Cremlyn, R. J. In Agrochemicals Preparation and Mode of Action Synthetic Insecticides II, Organophosphorus and Carbamate Compounds; John Wiley & Sons: UK, 1991; Ch. 6.
  3. Hwang, B. K.; Kim, C. H. Plant. Dis. 1995, 79, 221. https://doi.org/10.1094/PD-79-0221
  4. Parra, G.; Ristaino, J. B. Plant. Dis. 2001, 85, 1069. https://doi.org/10.1094/PDIS.2001.85.10.1069
  5. Georgakopoulos, D. G.; Fiddaman, P.; Leifert, C.; Malathrakis, N. E. J. Appl. Mircobiol. 2002, 92, 1078. https://doi.org/10.1063/1.1487918
  6. Cvitanich, C.; Judelson, H. S. Curr. Genet. 2003, 42, 228.
  7. Lee, H. B.; Kim, Y.; Kim, J. C.; Choi, G. J.; Park, S. H.; Kim, C. J.; Jung, H. S. J. App. Micro. 2005, 99, 836. https://doi.org/10.1111/j.1365-2672.2005.02684.x
  8. Park, S. Y.; Oh, H. K. Bull. Korean Chem. Soc. 2009, 30, 749. https://doi.org/10.5012/bkcs.2009.30.3.749
  9. Silva, D.; Norberto, F.; Santos, S.; Herves, P. J. Phy. Org. Chem. 2009, 22, 221. https://doi.org/10.1002/poc.1458
  10. Liu, D. Y.; Niu, J. B.; Zhao, L. N. Jangxi Shifan daxue Xuebao, Ziran kexueban 2007, 31, 566.
  11. Min, K. J. Kor. J. Env. Hlth. Soc. 1991, 17, 104.
  12. Choi, S. L.; Choi, Y. S.; Kim, Y. K.; Sung, N. D.; Kho, C. W.; Park, B. C.; Kim, E. M.; Lee, J. H.; Kim, K. M.; Kim, M. Y.; Myung, P. K. Arch. Pharm. Res. 2006, 29, 224. https://doi.org/10.1007/BF02969398
  13. Sung, N. D.; Myung, P. K.; Seong, M. G.; Yu, S. J.; Choi, S. L. Agri. Chem. Biotech. 2003, 46, 137.
  14. Albores-Velasco, M.; Thorne, J.; Wain, R. L. J. Agri. Food Chem. 1995, 43, 2260. https://doi.org/10.1021/jf00056a054
  15. Kochansky, J.; Cohen, C. F. J. Agri. Entomol. 1990, 7, 293.
  16. Martha, A. V.; John, T.; Ralph, L. W. J. Agric. Food Chem. 1995, 43, 2260. https://doi.org/10.1021/jf00056a054
  17. Sung, N. D.; Soung, M. G.; You, J. W.; Jang, S. C. Korean J. Pesticide Sci. 2006, 10, 157.
  18. Kubiny, H. 3D-QSAR in Drug Design: Theory, Methods and Applications; ESCOM: Leiden, 1993.
  19. Jang, S. C. Msc. Thesis, Graduate School of Chungnam National University, Korea, 2007.
  20. Tripos, S. Molecular modeling and QSAR software on CD-Rom (Ver.8.0); Tripos Associates, Inc., 1699 S. Hanley Road, Suit 303, St. Louis, MO. 63144-2913, U.S.A.
  21. Soung, M. G.; Lee, Y. J.; Sung, N. D. Bull. Korean Chem. Soc. 2009, 30, 613. https://doi.org/10.5012/bkcs.2009.30.3.613
  22. Soung, M. G.; Kil, M. J.; Sung, N. D. Bull. Korean Chem. Soc. 2009, 30, 2749. https://doi.org/10.5012/bkcs.2009.30.11.2749
  23. Clark, M.; Crammer, R. D., III.; Van Opdenbosh, N. J. Comput. Chem. 1989, 10, 982. https://doi.org/10.1002/jcc.540100804
  24. Murthy, V. S.; Kulkarni, V. M. Bioorg. Med. Chem. 2002, 10, 2267. https://doi.org/10.1016/S0968-0896(02)00056-1
  25. Dunn, W. J.; Wold, S.; Edlund, U.; Hellberg, S.; Gasteiger, J. Quant. Struct. Act. Relat. Chem. Bio. 1984, 3, 31.
  26. Crammer, R. D., III.; Bunce, J. D.; Patterson, D. E. Quant. Struct. Act. Relat. 1998, 7, 18.
  27. Kellogg, G. E.; Semus, S. F.; Abraham, D. J. J. Comput.-Aided Mol. Des. 1991, 5, 545. https://doi.org/10.1007/BF00135313
  28. Kang, K. Y.; Park, K. H.; Kang, J. K.; Leoniden, T.; Yang, D. H. N-2-Chloro-4-nitrophenylbenzenesulfonamide Derivatives Compounds Having Antifungal Activities against Phytopathogens and Method for Using Thereof. PA. KR 10-0538460. 2005.