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Relationships of Pesticide Octanol/Water Partition Coefficients to Their Physicochemical Properties

  • Fernando Sicbaldi
  • Attilio A. M. Del Re
Part of the Reviews of Environmental Contamination and Toxicology book series (RECT, volume 133)

Abstract

Chemodynamic theories estimate the fate, distribution, bioaccumulation potential, and approximate residence time of pollutants in the environment, all on the grounds of physicochemical properties. Mathematical models have been developed to use chemodynamic theories for prediction purposes (Mackay and Pater son 1981). Most of these models require input data on the physical and chemical properties of the compounds investigated.

Keywords

High Performance Liquid Chromatography Partition Coefficient Shake Flask Canonical Correlation Canonical Correlation Analysis 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. Agrochemicals handbook (1987) Royal Society of Chemistry, Nottingham, England.Google Scholar
  2. Berendsen GE, de Galan L (1980) Role of the chain length of chemically bonded phases and the retention mechanism in rever sed-phase liquid chromatography. J Chromatogr 196: 21–37.CrossRefGoogle Scholar
  3. Bowman BT, Sans WW (1983) Determination of octanol-water partitioning coefficient (Kow) of 61 organophosphorous and carbamate insecticides and their relationship to respective water solubility (S) values. J Environ Sci Hlth B18: (6): 667–683.CrossRefGoogle Scholar
  4. Briggs GG (1969) Molecular structure of herbicides and their sorption by soil. Nature (London) 223: 1288.CrossRefGoogle Scholar
  5. Briggs GG (1981) Theoretical and experimental relationships between soil adsorption, octanol-water partition coefficient, water solubilities, bioconcentration factors, and the Parachor. J Agrie Food Chem 29: 1050–1059.CrossRefGoogle Scholar
  6. Briggs GG, Bromilow RH, Evans AA (1982) Relationship between lipophilicity and root uptake and translocation of non-ionized chemical by barley. Pestic Sci 13: 495–504.CrossRefGoogle Scholar
  7. Brooke DN, Dobbs AJ, Williams N (1986) Octanol:water partition coefficient (P): Measurement, estimation, and interpretation, particularly for chemicals with P 105. Ecotoxicol Environ Saf 11: 251–260.PubMedCrossRefGoogle Scholar
  8. Bruggeman WA, van der Steen J, Hutzinger O (1982) Reversed-phase thin-layer chromatography of polynuclear aromatic hydrocarbons and chlorinated biphenyls. Relationship with hydrophobicity as measured by aqueous solubility and octanol-water partition coefficient. J Chromatogr 238: 335–346.Google Scholar
  9. Chessels M, Hawker DW, Connel DW (1991) Critical evaluation of the measurement of the 1-octanol/water partition coefficient of hydrophobic compounds. Chemosphere 22: 1175–1190.CrossRefGoogle Scholar
  10. Chiou CT, Freed VH, Schmedding DW, Kohnert RL (1977) Partition coefficient and bioaccumulation of selected organic chemicals. Environ Sci Technol 11: 475–478CrossRefGoogle Scholar
  11. Coy DW, Kew GA, Mullins ME, Piserchia PW (1986) Determining uncertainty in physical parameter measurements by Monte Carlo simulation. In: Garner WY, Honeycutt RC, Nigg HN (eds) Evaluation of pesticides in ground water. ACS, Washington, DC, pp 42–60.Google Scholar
  12. Cramer DR (1980) BC(DEF) parameters. 1. The intrinsic dimensionality of intermolecular interactions in the liquid state. J Am Chem Soc 102: 1837–1849.CrossRefGoogle Scholar
  13. de Bruijn J, Bussers F, Seinen W, Hermens JLM (1989) Determination of octanol/ water partition coefficients for hydrophobic organic chemicals with the “slow- stirring” method. J Environ Toxic Chem 8: 499–512.CrossRefGoogle Scholar
  14. de Bruijn J, Hermens JLM (1991) Uptake and elimination kinetics of organophophorous pesticides in the guppy ( Poecilia reticulata ): Correlations with the octanol/water partition coefficient. J Environ Toxic Chem 10: 791–804.Google Scholar
  15. de Kock AC, Lord DA (1987) A simple procedure for determining octanol-water partition coefficents using reverse phase high performance liquid chromatography ( RP-HPLC ). Chemosphere 16: 133–142.Google Scholar
  16. de Wolf W, de Bruijn JHM, Seinen W, Hermens JLM (1992) Influence of biotransformation on the relationship between bioconcentration factors, and octanol- water partition coefficents. Environ Sei Technol 26: 1197–1201.Google Scholar
  17. Doucette JW, Andren AW (1987) Correlation of octanol/water partition coeffi-cients and total molecular surface area for highly hydrophobic aromatic compounds. Environ Sei Technol 21: 821–824.CrossRefGoogle Scholar
  18. Dubelman S, Bremer MJ (1983) Determination of the octanol/water partition coefficient of MAPC products. Rept No MSL-3219, Monsanto Co, Agricultural Res Div, St. Louis, MO.Google Scholar
  19. Ellgehausen H, D’Hondt C, Fuerer R (1981) Reversed-phase chromatography as a general method for determining octan-l-ol/water partition coefficients. Pestic Sei 12: 219–227.CrossRefGoogle Scholar
  20. Ellgehausen H, Guth JA, Esser HO (1978) International congress on pesticide chemistry, 4th ed, v32, IUP AC, Zurich.Google Scholar
  21. Felsot A, Dham PA (1979) Sorption of organophosphorous and carbamate insecticides by soil. J Agrie Food Chem 27: 557–563.CrossRefGoogle Scholar
  22. Fujita T, Iwasa J, Hansch C (1964) A new substituent constant, TT, derived from partition coefficients. J Am Chem Soc 86: 5175–5180.Google Scholar
  23. Fürer R, Geiger M (1977) A simple method of determining the aqueous solubility of organic substances. Pestic Sei 8: 337–344.CrossRefGoogle Scholar
  24. Glass ADM (1975) Inhibition of phosphate uptake in barley roots by hydroxy- benzoic acids. Phytochemistry 14: 2127–2130.CrossRefGoogle Scholar
  25. Green G, Karichoff SW (1990) Pesticide in the soil environment: Processes impacts and modelling. In: Cheng H (ed), SSSA book series, vol 2. Madison, WI, pp 431–432.Google Scholar
  26. Hansch C, Leo A (1979) Subsituent constants for correlation analysis in chemistry and biology. Wiley-Inter science, New York.Google Scholar
  27. Harnisch M, Mockel H J, Schulze G (1983) Relationship between log Pow shake-flask values and capacity factors derived from reversed-phase high-performance liquid chromatography for n-alkylbenzenes and some OECD substances. J Chromatogr 282: 315–332.CrossRefGoogle Scholar
  28. Isnard P, Lambert S (1988) Estimating bioconcentration factors from octanol-water partition coefficient and aqueous solubility. Chemosphere 17: 21–34.CrossRefGoogle Scholar
  29. Kanazawa J (1981) Measurement of the bioconcentration factors of pesticides by freshwater fish and their correlation with physicochemical properties or acute toxicities. Pestic Sei 12: 417–424.CrossRefGoogle Scholar
  30. Kenaga EE, Goring CAI (1980) Relationship between water solubility, soil sorption, octanol-water partitioning, and concentration of chemicals in Biota. In: Eaton JG, Parrish PR, Hendricks AC (eds) Aquatic toxicology. ASTM, STP 707, Philadelphia, PA, pp 78–115.Google Scholar
  31. Kier LB, Hall LH (1986) Molecular connectivity in structure-activity analysis. Research Studies Press Ltd, Letchworth, Hertfordshire, England.Google Scholar
  32. Klein W, Kordel W, Weiß M, Poremski HJ (1988) Updating of the OECD test guideline 107 “partition coefficient n-octanol/water”: OECD laboratory inter- comparison test on the HPLC method. Chemosphere 17: 361–386.Google Scholar
  33. Konemann H, Zelle HR, Busser F, Hammers HE (1979) Determination of log Poct values of chloro-substituted benzenes, toluenes and anilines by high performance liquid chromatography on ODS-silica. J Chromatogr 178: 559–565.CrossRefGoogle Scholar
  34. Leo A, Hansch C, Elkins D (1971) Partition coefficient and their uses. Chem Rev 71: 525–616.CrossRefGoogle Scholar
  35. Mackay D, Paterson S (1981) Calculating fugacity. Environ Sci Technol 15: 1006–1014.CrossRefGoogle Scholar
  36. Mallhot H, Peters RH (1988) Empirical relationships between the 1-octanol/water partition coefficient and nine physicochemical properties. Environ Sci Technol 22: 1479–1488.CrossRefGoogle Scholar
  37. Mardia KV, Kent JT, Bibby JM (1989) Multivariate analysis, 7th ed. Harcourt Brace Jovanovich, Academic Press Ltd, London, pp 282–299.Google Scholar
  38. Miller MM, Ghodbane S, Wasik SP, Tewari YD, Martire DE (1984) Aqueous solubilities, octanol-water partition coefficients and entropies of melting of chlo-rinated benzenes and biphenyls. J Chem Eng Data 29: 184–190.CrossRefGoogle Scholar
  39. OECD Guidelines for testing of chemicals (1981) No 107, partition coefficient (n-octanol/water). Flask-shaking Method. Paris.Google Scholar
  40. OECD Guidelines for testing of chemicals (1989) No 117, partition coefficient (n-octanol/water). High performance liquid chromatography ( HPLC) method. Paris.Google Scholar
  41. Patil GS (1991) Correlation of aqueous solubility and octanol-water partition coeffi- cent based on molecular structure. Chemosphere 22: 723–738.CrossRefGoogle Scholar
  42. Poling SM, Hsu WJ, Yohoyama H (1975) Structure-activity relationships of chemical inducers of carotenoid biosynthesis. Phytochemistry 14: 1933–1938.CrossRefGoogle Scholar
  43. Pussemier L, Szabo G, Bulman RA (1990) Prediction of the soil adsorption coeffi-cient Koc for aromatic pollutants. Chemosphere 21: 1199–1212.CrossRefGoogle Scholar
  44. Rekker RF (1977) The hydrophobic fragmental constant. Its derivation and application, a means of characterizing membrane systems. Elsevier, Oxford.Google Scholar
  45. Sanborn JR, Metcalf RL, Bruce WN, Lu PY (1976) The fate of chlordane and toxaphene in a terrestrial-aquatic model ecosystem. Environ Entomol 5 (3): 533–538.Google Scholar
  46. SAS Institute Inc. (1985) SAS® user’s guide: Statistics, version 5 edition. Cary, NC.Google Scholar
  47. SAS Institute Inc. (1989) SAS/STAT® user’s guide, version 6, 4th ed, vol 1. Cary, NC.Google Scholar
  48. SAS Institute Inc. (1989) SAS/STAT® user’s guide, version 6, 4th ed, vol 2. Cary, NC.Google Scholar
  49. Shiu WY, Doucette W, Gobas FA, Andren A, Mackay D (1988) Physical-chemical properties of chlorinated dibenzo-B-dioxins. Environ Sci Technol 22: 651–658.CrossRefGoogle Scholar
  50. Shiu WY, Ma KC, Mackay D, Seiber JN, Wauchope RD (1990) Solubilities of pesticide chemicals in water. Part II: Data compilation. Rev Environ Contam Toxicol 116: 14–187.Google Scholar
  51. Snedecor GW, Cochran WG (1973) Statistical methods, 6th ed. Iowa State Univ Press, Ames, IA, pp 432–436.Google Scholar
  52. Suntio LR, Shiu WY, Mackay D, Seiber JN, Glotfelty D (1988) Critical review of Henry’s law constants for pesticides. Rev Environ Contam Toxicol 103: 1–59.CrossRefGoogle Scholar
  53. Thus JLG, Kraak JC (1985) Comparison of phenyl- and octadecyl-modified silica gel as stationary phase for the prediction of n-octanol-water partition coefficients by high-performance liquid chromatography. J Chromatogr 320: 271–279.CrossRefGoogle Scholar
  54. Verschueren K (1983) Handbook of environmental data on organic chemicals, 2nd ed. Van Nostrand Reinhold, New York.Google Scholar
  55. Wasik SP, Miller MM, Tewari YB, May WE, Sonnefeld WE, de Voe H, Zoller WH (1983) Determination of the vapor pressure, aqueous solubility, and octanol/water partition coefficient of hydrophobic substances by coupled generator column/liquid chromatographic methods. Residue Reviews 85: 29–42.Google Scholar
  56. Wauchope RD, Buttler TM, Hornsby AG, Augustjn Beckers PWM, Burt JP (1992) The SCS/ARS/CES pesticide properties database for environmental decisionmaking. Rev Environ Contam Toxicol 123: 1–155.PubMedCrossRefGoogle Scholar
  57. Woodburn KB, Doucette WJ, Andren AW (1984) Generator column determination of octanol/water partition coefficients for selected polychlorinated by phenils congeners. Environ Sei Technol 18: 457–459.CrossRefGoogle Scholar
  58. Worthing CR, ed (1987) The pesticide manual (a world compendium), 8th ed. British Crop Protection Council, Croydon, England.Google Scholar
  59. Worthing CR, Hance RJ, eds (1991) The pesticide manual (a world compendium), 9th ed. British Crop Protection Council, Croydon, England.Google Scholar

Copyright information

© Springer-Verlag New York, Inc. 1993

Authors and Affiliations

  • Fernando Sicbaldi
    • 1
  • Attilio A. M. Del Re
    • 1
  1. 1.Istituto di Chimica Agraria ed Ambientale, Facoltà di AgrariaUniversità Cattolica del Sacro CuorePiacenzaItaly

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