Browse > Article

Holographic Quantitative Structure-Activity Relationship (HQSAR) Analyses for the Herbicidal Activities of New Novel 2-(4-chloro-5-(2-chloroallyloxy)-2-fluorophenyl)-3-thioalkoxy-2,3,4,5,6,7-hexahydroisoindol-1-one Derivatives  

Sung, Nack-Do (Division of Applied Biologies and Chemistry, College of Agriculture and Life Science, Chungnam National University)
Song, Jong-Hwan (Cytosine Laboratory, Korea Research Institute of Chemical Technology)
Kang, Eun-Kyu (Division of Applied Biologies and Chemistry, College of Agriculture and Life Science, Chungnam National University)
Jung, Hoon-Sung (Division of Applied Biologies and Chemistry, College of Agriculture and Life Science, Chungnam National University)
Publication Information
The Korean Journal of Pesticide Science / v.9, no.3, 2005 , pp. 199-204 More about this Journal
Abstract
The herbicidal activities against barnyardgrass (Echinochloa crus-galli) by R-groups on the hexahydroisoindol-1-one ring of new 2-(4-chloro-5-(2-chloroallyloxy)-2-fluorophenyl) -3-thioalkoxy-2,3,4,5,6,7-hexahydroisoindol-1-one derivatives were studied using molecular holographic quantitative structure-activity relationships (HQSAR) methodology. Based on the results, the statistical results of the optimised HQSAR model (I-2) exhibited the best predictability and fitness for the herbicidal activities based on the cross-validated value ($r^2_{cv.}$ or $q^2=0.714$) and non-cross-validated value ($r^2_{ncv.}=0.922$), respectively. From the based graphical analyses of atomic contribution maps, herbicidal activities against barnyardgrass were confirmed depends upon the C4-C6 atoms of hexahydroisoindoline-l-one ring, carbon atom of ortho-position and meta-methyl group of 3-tolylthio substituent (8).
Keywords
2-(4-chloro-5-(2-chloroallyloxy)-2-fluorophenyl)-3-thioalkoxy-2,3,4,5,6,7-hexa-hydroisoindol-1-one; barnyard-grass (Echinochloa crus-galli); herbicidal activity; HQSAR model;
Citations & Related Records
연도 인용수 순위
  • Reference
1 Boger, P. and K. Wakabayashi (1999) Peroxidizing Herbicides, Springer-Verlag Berine, Heidelberg Germany
2 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. Reddy), ACS Symposium Series 719, American Chemical Society. Washington, DC
3 Lin, X., Z. Yang and L. Wang (2003) Three-dimensional quantitative structure-activity relationship study for phenylsulfonyl carboxylates using CoMFA and CoMSIA. Chemosphere. 53:945-952   DOI   ScienceOn
4 Tripos, Sybyl (2001) Molecular Modeling and QSAR Software on CD-Rom (Ver. 7.0), Tripos Associates, Inc., 1699 S. Hanley Road, Suite 303, St. Louis, MO. 63144-2913, U.S.A., http://www.tripos.com/Bookshelf/qsar/
5 Zhang, L., J. Wan and G. Yang, (2004) A DFT-based QSARs study of protoporphyrinogen oxidase inhibitors: phenyl triazolinones. Bioorg. Med Chem. 12: 6183-6191   DOI   ScienceOn
6 강은규 (2002) 2-(5-alkoxyphenyl)-3-phenylthioisoindoline-1-one 유도체들의 제초활성에 관한 3-thioalkoxy group의 효과. 석사학위논문, 충남대학교 대학원
7 Wan, J., G. Yang and C. G. Zhan (2004) Quantitative Structure-Activity Relationship for Cyclic Imide Derivatives of Protoporphyrinogen Oxidase Inhibitors: A Study of Quantum Chemical Descriptors from Density Fuctional Theory. J. Chem. Inf. Comput. Sci. 44:2099-2105   DOI   PUBMED
8 Fujita, T. (2002) : Similarities in bioanalogous structural transformation patterns, Ch.15, (ed. Baker, D. R. and N. K. Umetsu), In Agrochemical Discovery, Insect, Weed, and Fungal control ACS Symposium Series No. 774., American Chemical Society, Washington, DC
9 성낙도, 송종환, 박경용 (2004a) 비교분자 유사성 지수 분석 (CoMSIA) 방법에 따른 1-(5-methyl-3-phenyliso xazolin-5-yl)methoxy-2-chloro-4-fluorobenzene 유도체 들의 Protox 저해활성에 관한 이해. 한국응용생명화학회지, 47(4): 414-421
10 성낙도, 윤태용, 송종환, (2005) 새로운 2-alkoxyphenyl-3-phenylthioisoindoline-1-one 유도체들의 살균활성에 관한 분자 홀로그래피적인 정량적 구조와 활성과의 관계. 한국농약과학회지. 9(2):146-152
11 Kubiny, H., G. Felkers and Y. C. Martin (1998) 3D-QSAR in Drug Design. Dordrecht. Kluwer, Academic
12 Beale, S. I. and J. D. Weinstein (1990) Biosynthesis of Heme and Chlorophylls, H. A. Dailey ed., McGraw-Hill, New York, pp.287-391
13 Stahle, L. and S. Wold (1988) Multivariate data analysis and experimental design in biomedical research, Progr. Med Chem. 25:292-338
14 Theodoridis, G., J. T. Bahr, F. W. Hotzman, S. Sehgel and D. P. Suarez (2000) New geration of protox-inhibiting herbicides, Crop Protection, 19:533-535   DOI   ScienceOn
15 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 structure-activity relationship methods for large-scale prediction of chemicals binding to the estrogen receptor. J. Chem. Inf. Comput. Sci., 38:669-677   DOI   PUBMED
16 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
17 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)4-isoxazolecarboxamides and thier derivatives. J. Agric. Food Chem., 43:219-228   DOI   ScienceOn
18 성낙도, 송종환, 박경용 (2004c) 홀로그램(H) QSAR 방법에 따른 1-(5-methyl-3-phenylisoxazolin-5-yl)methoxy-2-chloro-4-fluorobenzene 유도체들의 Protox 저해 활성에 관한 이해. 한국응용생명화학회지, 47(3): 351-356
19 Hiraki, M., S. Ohki, Y. Sato, J. Jablonkai, P. Boger and K. Wakabayashi (2001) Protoporphyringen-IX oxidase inhibitors: Bioactivation of thiadiazolidines. Pesticide Biochem. and Physiology, 70:159-167   DOI   ScienceOn
20 Murata, S., Y. Kimura, T. Mabuchi and Y. Miura (2004) Accumulation of protoporphyrinogen IX prior to protoporphyrin IX in intact plants treated with ptotoporphyrinogen IX oxidase-inhibiting herbicides. J. Pestic. Sci., 29:195-199   DOI   ScienceOn
21 Lowis, D. R. (1997) HQSAR. A new, highly prediction QSAR technique. Tripos Technical Notes, Vol. 1., No.5
22 Mager, P. P. (1988) Multivariate Chemometrics in QSAR: A Dialogue. Letchworth, Hertfordshire, England, Wiley