2D-QSAR and HQSAR Analysis on the Herbicidal Activity of New Cyclohexanedione Derivatives

새로운 Cyclohexanedione계 유도체의 제초활성에 관한 2D-QSAR 및 HQSAR 분석

  • Kim, Yong-Chul (Division of Bayer Cror Science Ltd.) ;
  • Hwang, Tae-Yeon (Division of Applied Biology & Chemistry, College of Agriculture and Life Sciences, Chungnam National University) ;
  • Sung, Nack-Do (Division of Applied Biology & Chemistry, College of Agriculture and Life Sciences, Chungnam National University`)
  • 김용철 ((주)바이엘 크롭사이언스) ;
  • 황태연 (충남대학교 농업생명과학대학 응용생물화학부) ;
  • 성낙도 (충남대학교 농업생명과학대학 응용생물화학부)
  • Published : 2008.03.31


QSARs (Quantitative structure-activity relationships) between a series of new cyclohexanedione derivatives (5-benzofuryl-2-[1-(alkoxyimino)-alkyl]-3-hydroxycyclohex-2-en-1-ones) and their herbicidal activity against Rice plant (Oryza sativa L.) and Barnyard grass (Echinochloa crus-galli.) were discussed quantitatively using 2D-QSAR and holographic (H) QSAR methods. Generally, the HQSAR models have better predictability and fitness than the 2D-QSAR models. The herbicidal activities against Barnyard grass with 2D-QSAR II model were dependent upon Balaban indice (BI) of molecule and hydrophobicity of $R_1$ and $R_3$ group. And also, the $R_3=ethyl$ group, according to the information of the optimized HQSAR IV model, was more contribute to the herbicidal activities against Rice plant, while the 5-(cyclohex-3-enyl)-2,3-dihydrobenzofuran ring part was not contribute to the herbicidal activities against two plants.


2D-QSAR;HQSAR;Cyclohexanediones;5-benzofuryl-2-[1-(alkoxyimino)alkyl]-3-hydroxycyclohex-2-en-1-ones;Herbicidal activity;Rice Plant;Barnyard grass


  1. Amit, S., Corwin. N., Mani, V. S., Richard, J. A. and Malcolm, D. D. (2004) Use of Resistant ACCase Mutants To Screen for Novel Inhibitors against Resistant and Susceptible Forms of ACCase from Grass Weeds., J. Agric. Food Chem. 52:5144-5150. https://doi.org/10.1021/jf034738m
  2. Burton, J. D., J. W. Gronwald, R. A. Keith, D. A. Somers, B. G. Gegenbach and D. L. Wyse (1991) Kinetics of inhibition of acetyl-coenzyme A carboxylase by sethoxydim and haloxyfop., Pestic Biochem Physiol. 39:100-109 https://doi.org/10.1016/0048-3575(91)90130-E
  3. Hanch, C. (1976) The structure of medicinal chemistry. J. Med. Chem. 19:1-6 https://doi.org/10.1021/jm00223a001
  4. Harwood, J. L. (1988) Fatty acid metabolism., Annu Rev Plant Physiol. 39:101-138 https://doi.org/10.1146/annurev.pp.39.060188.000533
  5. Lowis, D. R. (1997) HQSAR. A new, highly prediction QSAR technique. Tripos Technical Notes, Vol. 1. (5):1-10
  6. Sung, N. D., J. H. Song and D. J. Jeon (2001) Structure and herbicidal activity relationship of the 2,3-dihydro-2,3,4,6,7- pentamethylBenzeofuran-5-yl substituents in 5-benzofuryl-2- 2-(alkoxyimino)-alkyl-3-hydroxycyclohex-2-en-1-ones. Kor. J. Pest. Sci. 5(3):12-14
  7. Sung, N. D., J. H. Song and H. R. Kim (2000) Structure activity relationship on the herbicidal activity of the 2,3-dihydro- 2,2,4,6,7-pentamethylbenzo-furan-5-yl substituents in 5- benzofuryl-2-1-(alkoxyimino)alkyl-3-hydroxycyclohex-2-en-1-one derivatives. Kor. J. Pestic. Sci. 4(3):47-51
  8. Myung, P. K. and N. D. Sung (2007) 2D-QSAR and HQSAR of the inhibition of Calineurin-NFAT signaling by blocking protein-protein interaction with N-(4-oxo-1(4H)- naphthalenylbenzenesulfonamide analogues. Arch. Pharm. Res. 30:976-983 https://doi.org/10.1007/BF02993966
  9. Tripos, Sybyl (2007) Molecular Modeling and QSAR Software on CD-ROM (Ver. 7.3), Tripos Associates, Inc., 1699 S. Hanley Road, Suite 303, St. Louis, MO. 63144-2913, U.S.A., http://www.tripos.com/bookshelf/qsar/
  10. TSAR (Ver. 3.3) (2000) Proprietary Software, Oxford Molecular Ltd
  11. Kim, Y. C. (2004) Analyses of 2D-QSAR and HQSAR on the herbicidal activity of new cyclohexanone derivatives. A Thesis for the Degree of Master in Agricultural Sciences, Chungnam National University
  12. Kubinyi, H. (1990) The Free-Wilson method and its relationship to the extrathermodynamic approach. Vol. 4. pp. 589-638., In Comprehensive Medicinal Chemistry, (Hansch, C. ed.) Pergamom Press. New York
  13. Mager, P. P. (1998) Multivatiate Chemometrics in QSAR: A Dialogue. Letchworth, Hertfordshire, England, Wiley
  14. Zhang, X. Q. and S. B. Powles (2006) The molecular bases for resistance to acetyl co-enzyme A carboxylase (ACCase) inhibiting herbicides in two target-based resistant biotypes of annual ryegrass (Lolium rigidum)., Planta. 223:550-557 https://doi.org/10.1007/s00425-005-0095-x
  15. SAS (2002) Statistics & Analysis Software on CD-ROM (Ver. 9.1), SAS Institute Inc., Cary, NC, 27513 U.S.A., http://www.sas.com/software/
  16. Devin, M. D. and R. H. Shimabukuro (1994) Resistance to acetyl coenzyme A carboxylase inhibiting herbicides. pp 141-169. In Powles SB, Holtum JAM (eds) Herbicide resistance in plants: biology and biochemistry., Lewis Publishers, Boca Raton
  17. Broka, J. B. and M. Randie (1996) Application of String Comparison Techniques in QSAR studies. J. Com. Chem. 7:176-188
  18. Heritage, T. W. and D. R. Lowis (1999) Molecular hologram QSAR. Ch. 4., In Rational drug design: Novel Methodology and Practical Applications (ed. Parrill, A. L. and M. R.), ACS Symposium Series 719, ACS. Washington, DC
  19. Konishi, T. and Y. Sasaki (1994) Compartimentalization of two forms of acetyl-CoA carboxylase in plants and the origin of their tolerance towards herbicides., Proc Natl Acad Sci USA. 91:3598-3601
  20. Stahle, L. and S. Wold (1988) Multivariate data analysis and experimental design in biomedical research, Progr. Med. Chem. 25:292-338
  21. White, G. M., S. R. Moss and A. Karp (2005) Differences in the molecular basis of resistance to the cyclohexanedione herbicide sethoxydim in Lolium multiflorum., Weed Research. 45:440-448 https://doi.org/10.1111/j.1365-3180.2005.00478.x