Browse > Article

Development of new agrochemicals by qnantitative structure-activity relationship (QSAR) methodology. II. The linear free energy relationship (LFER) and descriptors  

Sung, Nack-Do (Division of Applied Biology & Chemistry, College of Agriculture & Life Sciences, Chungnam National University)
Publication Information
The Korean Journal of Pesticide Science / v.6, no.4, 2002 , pp. 231-243 More about this Journal
Abstract
Starting with linear free energy relationships (LFER), drug design to mimic of the activated complexes at transition state, and hydrolysis mechanisms to control the potency and residual properties of pesticides were introduced and summarized for the necessity. In order to understand the searching or development of new agrochemicals by two dimensional quantitative structure-activity relationship (2D QSAR) methodology, a series of the various descriptors, steric constants, electronic constants including quantum pharmacological parameters and hydrophobic constants were classified and discussed for results of the several studied cases. In addition, the processes of development of new agrochemicals by QSAR techniques were introduced simply.
Keywords
LFER; Physicochemical descriptors; Quantum pharmacology; Electronic parameters; Steric parameters; Hydrophobic parameters; DSP (dual substituent parameter); Development process;
Citations & Related Records
연도 인용수 순위
  • Reference
1 Schloss, J. V. (1988) Significance of slow binding enzyme inhibition and its relationship to reaction intermediate analogs, Acc. Chem. Res. 21:348-353
2 성낙도 (2002a) 정량적인 구조-활성상관 (QSAR) 기법에 의한 새로운 농약의 개발. I. 기본개념과 QSAR기법의 유형. 한국농약과학회지 6(3):166-174
3 Craig, P. N. (1971) Interdependence between physical parameters and selection of substituent groups for correlation studies, J. Med. Chem. 14:680-684
4 Dugas, H. (1989) Bioorganic Chemistry, Ch.3, pp.128. Springer-Verlag, New York
5 Fujita, T. (1983) Substitution effects in the partition coefficient of disubstituted benzenes: Bidirectional Hammett-type relationships. pp. 75 -113, Vol. 14, In Progress in Physical Organic Chemistry (ed. Taft. R. W.). John Wiley & Sons., ronto
6 Fujita, T., T. Nishioka and M. Nakajima (1977) Hydrogenbonding parameter and its significance in quantitative structure-activity studies, J. Med. Chem., 20;1071-1081
7 Gallo, R. (1983) Treatment of steric effect, pp.115-163. Vo. 14., In Progress in Physical Organic Chemistry (ed. Taft. R. W.). John Wiley & Sons., Toronto
8 Johnson, C. D. (1980) The Hammett Equation. Cambridge University Press, Cambridge
9 Knipe A. C. (1987) Addition reactions: Polar addition, Ch. 13. pp. 309 & pp. 400., In Organic Reaction Mechanisms 1984 (Knipe, A. C. and W. E. Watts ed.). John Wiley & Sons, Toronto
10 Richards, W. G. (1972) Quantum Pharmacology, Ch. 11., Butterworths. London, Boston
11 Shorter, J. (1981) Nucleophilic aliphatic substitution. Ch. 9. p.344. In Organic Reaction Mechanisms 1979 (Knipe, A. C. and W. E. Watts ed.). John Wiley & Sons, Toronto
12 Wells, P. R. (1963) Linear free energy relationships, Chem. Rev. 63;171-219
13 성낙도 (2002b) 살충제, O,O-diethyl-O-(1-phenyl-3-trifluo-romethylpyrazol-5-yl) phospho-rothioate(Flupyrazofos)의 가수분해 반응 메카니즘. 한국농약학회지 6(3):218-223
14 Wexler, R. R., W. J. Greenlee, J. D. Irvin, M. R. Goldberg, K. Prendergast, R. D. Smith and P. B. Tinmlermans (1996) Nonpeptide angiotensin II receptor antagonists: The next generation in antihypertensive theraphy, J. Med. Chem. 39:625-656
15 성닥도 (1989c) 왜, m-methyl 치환 살충제들은 강한 살충작용을 나타낼까? Phenyl N-methylcarbamate와 m-xylyl-N-methylcarbamate 유도체들에 관하여 . 한국농화학회지 32(2):170-177
16 성낙도, 박현주, 박승희, 변종영 (1991) Benzotriazole계 유도체의 제초활성과 분자설계. 한국농화학회지 34(3):287-294
17 Shorter, J. (1982) Nucleophilic aliphatic substitution. Ch 9. p. 344. In Organic Reaction Mechanisms 1981 (Knipe, A. C. and W. E. Watts ed.). John Wiley & Sons, Toronto
18 Fleming, I. (1976) Frontier Orbitals and Organic Chemical Reactions, Ch. 3., p.37. John Wiely & Sons, Toronto
19 Chapman, N. B. and J. Shorter (1978) Correlation Analysis in Chemistry: Recent Advances. Plenum Press, New York and London
20 Hansch, C. and A. Leo (1995b) Exploring QSAR: Fundamentals and Applications in Chemistry and Biology. ACS Professional Reference Book, American Chemistry Society, Washington, DC
21 Shorter, J. (1987) Nucleophilic aliphatic substitution. Ch. 10. p.319, In Organic Reaction Mechanisms 1984 (Knipe, A C. and W. E. Watts ed.). John Wiley & Sons, Toronto
22 성낙도 (1989a) 1-(phenoxymethyl)benzotriazole 유도체 중 methylene 양성자의 chemical shift에 관한 자유에너지 관계의 조성과 용매 의존성. 대한화학회지 33(5):538-544
23 Isaacs, N. S. (1987) Physical Organic Chemistry, Ch. 4, Longman Scientific & Technical, New York, U.S.A.
24 Spilllane, W. J. (1987) Reactions of acids and their derivatives. etc., Ch. 2. p.46, In Organic Reaction Mechanisms 1984 (Knipe, A. C. and W. E. Watts ed.). John Wiley & Sons, Toronto
25 성낙도, 이광재, 김용집, 김대황 (1996) 제초성 Flaza sulfuron의 Smile 자리옮김 반응. 한국농화학회지 39(1):455-462
26 Gallop, M. A., R. W. Barrett, W. J. Dower., S. P. A. Fodor and E. M. Gardn (1994)Applications of combinatorial technologies to drug discovery. I. Back ground and peptide combinatorial libraries, J. Med. Chem. 37:1233-1251
27 Kansy, M. (1996) Molecular properties, Ch.2., In Structure-Property Correlations in Drug Research (ed. Waterbeernd, H. V. D.). Academic Press, R. G. Landes Co. Austin
28 성낙도, 박승희 (1983) Dimethyl-2,2-dichlorovinylphosphate(DDVP)의 분해반응에 관한 연구. 한국농화학회지 26(2):125-131
29 Cox, R. A. (1987) Carbocation, Ch. 9. pp. 292, In Organic Reaction Mechanisms 1984 (Knipe, A. C. and W. E. Watts ed.). John Wiley & Sons, Toronto
30 Kubinyi, H. (1988) Free Wilson analysis. Theory,applications and its relationship to Hausch analysis, Quant. Sruct.-Act. Relat. 7:121-133
31 성낙도, 박승희, 명평근, 전용구, 이천배 (1986) 살충성 O,O-diethylphenylphosphate유도체의 형태와 반응성에 관한 분자 괘도론적 연구. 한국식물보호학회지 24(4):231-238
32 Leo, A., C. Hausch and P. Y. C. Jow (1976) Dependence of hydrophobicity of a polar molecules on their molecular volume, J. Med. Chem. 19:611-615
33 성낙도, 권기성, 김태린 (1989d) Strylylphenylsulfone 유도체의 가수분해 반응 메카니즘과 반응속도론. 대한화학회지 33:120-126
34 Hansch, C. and T. Fujita (1964) Rho-sigma-pi analysis. A method for the correlation of biological activity and chemical structure, J. Am. Chem. Soc. 86:1616-1626
35 Swain, C. G. and E. C. Lupton, Jr. (1968) Field and resonance components of substituent effects, J. Am. Chem. Soc. 90:4328-4337
36 Dunn, W. J. III (1977) Molar refractivity as an independent variable in quantitative structure-activity studies. Eur. J. Med. Chem. 12;109-127
37 Lowry, T. H. and K. S. Richardson (1981) Mechanism and Theory in Organic Chemistry, Ch. 7, pp.508, Harper & Row Pub., New Yark
38 CMC (1996) Computational medicinal chemistry; CMC modeling guid, computer aided molecular design, QSAR. Faculty of pharmacy Utecht university; www.cmc.pharma.un.nl, Netherland
39 Wohl, A. J. (1971) A molecular orbital approach to quantitative drug design, Ch.4, pp.381-449. Vol. 3., In Drug Design (ed. E. J. Ariens), Academic Press, New York and London
40 Hansch, C. and A. J. Leo (1979) Substituent Constants for Correlation Analysis in Chemistry and Biology. John Wiely & Sons, New York
41 Taft, R. W. Jr (1965) Steric Effects in Organic Chemistry (ed. Newman, M. S.). pp.556-675, Wiley & Sons, New York
42 Andrew, P. R. and D. A. Winkler (1984) The design and medical applications of transition state analogues, pp. 147., In Drug Design; Fact or Fantasy? (ed. Jolles, J. and K. R. H. Wooldbridge, ed.), Academic Press, London
43 Fujita, T. and T. Nishioka (1976) The analysis of the ortho effects. pp.49-89. Vol.12. In Progress Physical Organic Chemis$\sigma$y (ed. R. W. Taft), John Wiley & Sons., Toronto
44 Topliss, J. G. (1972) Utilization of operational schemes for analog synthesis in drug design., J. Med. Chem. 15:1006-1011
45 Westheimer, F. H. (1968) Pseudo-rotation in the hydrolysis of phosphate esters, Ace. Chem. Res. 1:70-78
46 Accelrys: $Cerius^2$ QSAR+, Insight II, Catalyst program package (Imagene). Molecula Simulations Inc. & www.sinica.edu.tw
47 Verloop, A., W. Hoogenstraaten and J. Tipker (1976) Development and application of new steric substituent parameters in drug design, Vol. 7., pp. 165-207. In Drug Design (ed. E. J. Ariens). Academic Press, New York
48 성낙도, 유성재, 최경섭, 권기성 (1998) 살충제, Buprofezin의 가수분해 반응 메카니즘. 한국농약과학회지 2(1):45-52
49 성낙도, 박천규, 박문규, 권기성, 김태린 (1985) 핵자기 공명 분광법에 의한 N-benzylidene aniline 유도체중 imidoyl proton의 chemical shift에 미치는 자유 에너지 관계. 대한화학회지 29(3):277-282
50 성낙도, 명평근, 이천배, 유병태 (1989b) 살충성, O,O-dimethylphenylphosphate 유도체들에 의한 acetyl-cholinesterase의 phosphorylation에 관한 양자 약리학적 연구.충남대 약학논문집 2:21-26
51 Charton, M. (1981) Electrical effect substituent constants for correlation analysis., pp.119-251. Vol. 13. In Progress in Physical Organic Chemistry. (ed. R. W.Taft), John Wiley & Sons. Inc., Toronto
52 Denney, R. C. (1969) Named Organic Reactions, pp.43, Butterworths & Co. Ltd., London
53 성낙도, 이찬복, 류재옥, 김대황 (1995a) 제초성 N-(2 ,6-dimethoxypyrimidin-2-yl)aminocarbonyl-2-치환(Z)-6-(1-hydroxy-2-fluoroethyl)benzenesulfonamide 유도체의 가수분해 반응에카니즘. 한국농화학회지 38(5):455-462
54 성낙도, 유성재, 전동주, 김대황 (1995b) Phenylvinyl sulfone 유도체의 제초활성. 한국농화학회지, 38:90-94
55 성낙도, 유성재, 강문성 (1997) 살충성 imidacloprid의 가수분해 반응 메카니즘. 한국농화학회지 40(1):53-57
56 Sung, N. D. (2000) Collected Works. Reaction Kinetics & Mechanism; Exploring QSARs. pp.305-640, OB Planning Co.
57 성낙도, 이숙주, 윤세중, 권기성, 김태린 (1988) N-($\rho$-chloro-benzoyl)-C-phenoxyimidoyl chloride 유도체 중 작용기들의 신축 흡수에 미치는 자유 에너지 관계. 대한화학회지 32(5):507-509
58 성낙도, 김현이, 박천규 (1994) 살충성 O,O-diethyl-$\alpha$-cyanobenzylideneaminooxyphos-phorothioate(Volaton)의 가수분해 반응메카니즘. 한국농화학회지 37(2):124-129
59 성낙도, 윤태용, 권기성, 김태린 (1990) 살충성 2-chloro-1-(2,4,5-trichlorophenyl)vinyldimet-hylphosphate(Gardona)의 가수분해 반응메카니즘. 대한화학회지 34(5):483-489
60 McCall, J. M. (1975) Liquid-liquid partition coefficients by high-pressure liquid chromatography, J. Med. Chem. 18:549-552
61 성낙도 (1984) 살충성, O,O-Diethylphenylphosphate 유도체들에 의한acetylcholinesterase의 phosphorylation에 미치는 자유에너지 관계. 충남대 농업과학연구 11(1):176-181
62 Tomlin, C. ed., (1997) The Pesticides Manual, (11th ed.), p.140, p.677 & p.1163, Crop Protection Publications, Surrey, U. K.