Molecular Holographic Quantitative Structure-Activity Relationship (HQSAR) for the Fungicidal Activities of New Novel 2-Alkoxyphenyl-3-phenylthioisoindoline-1-one Derivatives

새로운 2-Alkoxyphenyl-3-phenylthioisoindoline-1-one 유도체들의 살균활성에 관한 분자 홀로그래피적인 정량적 구조와 활성과의 관계

  • Sung, Nack-Do (Division of Applied Biologies and Chemistry, College of Agriculture and Life Science, Chungnam National University) ;
  • Yoon, Tae-Yong (Research Institute, Dong-bang Agro Corporation) ;
  • Jung, Hoon-Sung (Division of Applied Biologies and Chemistry, College of Agriculture and Life Science, Chungnam National University)
  • 성낙도 (충남대학교 농업생명과학대학 응용생물화학부) ;
  • 윤태용 (동방아그로(주) 연구소) ;
  • 정훈성 (충남대학교 농업생명과학대학 응용생물화학부)
  • Published : 2005.06.30


The fungicidal activities against resistance phytophthora blight (RPC; 95CC7303) and sensitive phytophthora blight (Phytopthora capsici) (SPC; 95CC7105) by new 2-alkoxyphenyl-3-phenylthioisoindoline-1-one derivatives (A & B) were studied using molecular holographic quantitative structure activity relationships (HQSAR) methodology. Based on the results, the statistical results of the two best HQSAR models, RI-B for RPC and SII-A for SPC exhibited the best predictability and fitness for the fungicidal activities based on the cross-validated value ($q^2=0.806{\sim}0.865$) and non cross-validated value ($r^2_{ncv.}=0.921{\sim}0.952$, respectively. The quality of the model for SPC was slightly than that of RPC. From the based graphical analyses of atomic contribution maps, it was confirmed that the novel selective character for fungicidal activities against RPC depends upon the 2-fluoro-4-chloro-5-alkoxyanilino group.


  1. Boger, P. and K. Wakabayashi (1990) Peroxidizing Herbicides, Springer-Verlag Berline Hidelberg. Germany
  2. Fujita, T. (2002) In Agrochemical Discovery, Insect, Weed and Fungal control: Similarities in bioanalogous structural transfonnation patterns, Ch.15, (ed. Baker, D. R and N. K. Umetsu) ACS Symposium Series No. 774., American Chemical Society, Washington, DC
  3. Hamper, B. C., K. L. Leschinsky, S. S. Massey, C. L. Bell, L. H. Brannigan and S. D. Prosch (1995) Synthesis and herbicidal activity of 3-aryl-5-(haloalkyl)-4isoxazolecarboxamides and thier derivatives. J. Agric. Food Chem., 43:219-228
  4. Heritage, T. W. and D. R Lowis (1999) In Rational drug design; Novel Methodology and Practical Applications: Molecular hologram QSAR. Ch. 4., (ed. Parrill, A. L. and Reddy, M. R), ACS Symposium Series 719, American Chemical Society. Washington, DC
  5. Joo, G. J. (2005) Production of an anti-fungal substance for biological control of Phytophthora capsici causing phytophthora blight in red-peppers by Streptomyces halstedii. Biotechnology Letters. 27:201-205
  6. Kubiny, H., Felkers, G. and Martin, Y. C. (1998) 3DQSAR in Drug Design. Dordrecht. Kluwer, Academic press
  7. Lowis, D. R (1997) HQSAR. A new, highly prediction QSAR technique. Tripos Technical Notes, Vol. 1., No. 5
  8. Mager, P. P. (1988) Multivariate Chemometrics in QSAR: A Dialogue. Letchworth, Hertfordshire, England, Wiley
  9. Pallett, K. E. (1997) Herbicide target sites, recent trends and new challenges. Proceeding of Brighton Crop Protection Conference-Weeds, 575-578
  10. Stahle, L. and S. Wold (1988) Multivariate data analysis and experimental design in biomedical research, Progr. Med. Chem. 25:292-338
  11. Theodoridis, G., J. T. Bahr, F. W. Hotzman, S. Sehgel and D. P. Suarez (2000) New geration of protoxinhibiting herbicides, Crop Protection, 19:533-535
  12. Tong, W. D., R. Lowis, R. Perkins, Y. Chen, W. J. Welsh, D. W. Goddette, T. W. Heritage and D. M. Sheehan (1998) Evaluation of quantitative structureactivity relationship methods for large-scale prediction of chemicals binding to the estrogen receptor. J. Chem. Inf. Comput. Sci., 38:669-677
  13. Tripos Associates, Inc., 1699 S. Hanley Road, Suite 303, St. Louis, MO. 63144-2913, U.SA,
  14. 성낙도, 송종환, 박경용 (2004a) 비교분자 유사성 지수분석(CoMSIA) 방법에 따른 1-(5-methyl-3-phenylisoxazolin-5-yl)methoxy-2-chloro-4-fluorobenzene 유도체들의 Protox 저해활성에 관한 이해. 한국응용생명화학회지, 47(4):414-421
  15. 성낙도, 송종환, 박경용 (2004b) 비교 분자장 분석(CoMFA) 방법에 따른 1-(5-methyl-3-phenylisoxazolin-5-yl)methoxy-2-chloro-4-fluorobenzene 유도체들의 Protox 저해활성에 관한 이해. 한국농약과학회지, 8(3):151-161
  16. 성낙도, 송종환, 박경용 (2004c) 홀로그램(H) QSAR 방법에 따른 1-(5-methyl-3-phenylisoxazolin-5-yl)methoxy2-chloro-4-fluorobenzene 유도체들의 Protox 저해활성에 관한 이해. 한국응용생명화학회지, 47(3):351-356
  17. 성낙도, 윤태용, 송종환, 정훈성 (2005a) 상이한 정렬에 따른 비교 분자장 분석(CoMFA) 방법을 이용한 새로운 2-alkoxyphenyl-3-phenylthioisoindoline-l-one 유도체들의 살균활성에 관한 3차원적인 정량적 구조와 활성과의 관계. 한국응용생명화학회지, 48(1): 82-88
  18. 성낙도, 윤태용, 송종환, 정훈성 (2005b) 상이한 정렬에 따른 비교분자 유사성 지수분석 (CoMSIA) 방법을 이용한 새로운 2-alkoxyphenyl-3-phenylthioisoindoline-1-one 유도체들의 살균활성에 관한 3차원적인 정량적 구조와 활성과의 관계. 한국농약과학회지, 9(1):26-34