Browse > Article

Comparative Molecular Field Analyses on the Herbicidal Activities of New 5-benzofuryl-2-[1-(alkoxyimino)alkyl]-3-hydroxycyclohex-2-en-1-one Derivatives  

Chung, Ki-Sung (Korea Research Association of Agrochemicals)
Jang, Seok-Chan (Division of Applied Biology and Chemistry, College of Agriculture and Life Science, Chungnam National University)
Choi, Kyung-Seob (Division of Applied Biology and Chemistry, College of Agriculture and Life Science, Chungnam National University)
Sung, Nack-Do (Division of Applied Biology and Chemistry, College of Agriculture and Life Science, Chungnam National University)
Publication Information
Applied Biological Chemistry / v.49, no.3, 2006 , pp. 238-242 More about this Journal
Abstract
The herbicidal activities against the pre-emergence of rice plant (Oryza sativa L.) and barnyard grass (Echinochloa crus-gall) with changing substituents $(R_1-R_4)$ of new 5-benzofuryl-2-[1-(alkoxyimino) alkyl]-3-hydroxycyclohex-2-en-1-one derivatives as substrate molecules were studied quantitatively using comparative molecular field analyses (CoMFA). The optimized CoMFA models (rice plant: A5 & barnyard grass: B3) were derived from atom based fit alignment and a combination of CoMFA fields. The two models for herbicidal activity against two plants showed the best predictability and fitness ($q^2$>0.6 & ${r^2}_{ncv.}$>0.94) for the herbicidal activities. Also, CoMFA-HINT contour maps showed that the selective herbicidal activity between rice plant and barnyard grass depends on the hydrophobicity of $R_2\;and\;R_3$ groups in molecule. Therefore, it is expected that the herbicidal activity against barnyard grass will be improved by the introduction of the steric bulk small and hydrophobic group.
Keywords
5-benzofuryl-2-[1-(alkoxyimino)alkyl]-3-hydroxycyclohex-2-en-1-ones; Echinochloa crus-galli; postemergence herbicidal activity; CoMFA model;
Citations & Related Records
Times Cited By KSCI : 1  (Citation Analysis)
연도 인용수 순위
1 Lichtenthaler, H. K. (1990) Mode of action of herbicides affecting acetyl-CoA carboxylase and fatty acid biosynthesis. Z. Naturforsch., C: J. Biosci. 45C, 521-528
2 Tripos, Sybyl (2001) In Molecular Modeling and QSAR software on CD-Rom (Ver. 7.1), Tripos Associates, Inc., Suite 303, St. Louis, MO
3 Sung, N. D., Song, J. H. and Kim, K. M. (2000) Structure activity-relationships on the herbicidal activity of the 2,3- dihydro-2-ethyl-2,4,6,7-tetramethylbenzofuran-5-yl substituents in 5-benzofurl-2-[1-(alkoxyimino)alkyl]-3-hydroxycyclohex-2- en-1-one derivatives. Kor. J. Pestic. Sci. 4, 34-39
4 Sung, N. D., Song, J. H. and Kim, K. M. (2000) Structure activity-relationships on the herbicidal activity of the 2,3-dihydro-2,2,4,6,7-pentamethylbenzofuran-5-yl substituents in 5-benzofuryl-2-[1-(alkoxyimino)alkyl]-3-hydroxycyclohex-2-en-1-one derivatives. Kor. J. Pestic. Sci. 4, 47-51
5 Kellogg, G. E., Semus, S. F. and Abraham, D. J. (1991) HINT:A new method of empirical hydophobic field calculation for CoMFA. J. Comput.-Aided Mol. Des. 5, 545-552   DOI
6 Cocker, K. M., Coleman, J. O. D., Blair, A. M., Clarke, J. H. and Moss, S. R. (2000) Biochemical mechanisms of crossresistance to aryloxyphenoxypropionate and cyclohexanedione herbicides in populations of Avena spp. Weed Res. 40, 323-334   DOI   ScienceOn
7 Hoppe, H. H. (1980) Changes in membrane permeability, carbohydrate content, lipid content, and lipid composition in root tips from Zea mays after treatment with diclofop-methyl. Z. Pflanzenphysiol. Bd. 100S, 414-426
8 Kuk, Y. I., Jingrui, W., Jeffrey, F. D. and Kriton, K. H. (1999) Mechanism of Fenoxaprop Resistance in an Accession of Smooth Crabgrass (Digitaria ischaemum) Pesti. Biochem. physiol. 64, 112-123   DOI   ScienceOn
9 White, G. M., Moss, S. R. and Karp, A. (2005) Differences in the molecular basis of resistance to the cyclohexanedione herbicide sethoxydim in Lolium multiflorum. Weed Res. 45, 440-448   DOI   ScienceOn
10 Kubinyi, H (1993): 3D QSAR Drug Design, Theory, Methos and Applications, ESCOM. Leiden
11 Robert, D. C., Peter, C. F. (2004) Statistical variation in progressive scrambling. J. Comp.-Aided Mol. Des. 18, 563-576   DOI
12 Web, S. R. and Hall, J. C. (2000) Monoclonal-based ELISA for the identification of herbicidal cyclohexanedione analogues that inhibit graminaceous acetyl coenzyme-A carboxylase. J. Agric. Food Chem. 48, 1210-1218   DOI   ScienceOn
13 Jung, K. S. (2004) 3D-QSAR of ACCase II inhibiting herbicidal agent by cyclohexanedione derivatives using CoMFA and CoMSIA. M.Sc. Degree Thesis. Graduate School, Chungnam National University, Daejeon, Korea
14 Cramer, R. D., Bunce, J. D. and Patterson, D. E. (1988) Crossvalidation, Bootstrapping, and partial least squares compared with multiple regression in conventional QSAR studies. Quant. Struct. Act. Relat. 7, 18-25   DOI
15 Seng, T. W., Skillman, T. R., Yang, N. and Hammond, C.(2003), Cyclohexanedione hrerbicides are inhibitors of rat heart acetyl-CoA carboxylase. Bioorg. Med. Chem. 13, 3237-3242   DOI   ScienceOn
16 Cramer, R. D., Patterson, D. E. and Bunce, J. D. (1988) Comparative molecular field analysis (CoMFA), 1. Effect of shape on the binding of steroids to carrier proteins, J. Am. Chem. Soc. 110, 5959-5967   DOI   ScienceOn
17 Boger, P. and Wakabayashi, K. (2002) In Herbicide classes in development, Springer-Verlag, Berlin
18 Sung, N. D., Jung, K. S., Jung, H. S. and Chung, Y. H. (2006) Comparative molecular similarity analysis (CoMSIA) on the herbicidal activities of new 5-benzofuryl-2-[1-(alkoxyimino) alkyl]-3-hydroxycyclo-hex-2-en-1-one derivatives. Kor. J. Pestic. Sci. 10, 7-14   과학기술학회마을