Quantitative structure-activity relationships for the acute toxicity of chlorobenzenes to Daphnia magna

The relationships between physical-chemical properties of aqueous solubility, octanol/water partition coefficient, vapor pressure, boiling and melting points and Henry's Law constant are discussed and illustrated for the chlorobenzenes. It is suggested that a critical review of such data is an essential component of quantitative structure-activity relationship (QSAR) development and can elucidate the potential for air/water and organism/water partitioning during bioas-says. Experimental 48-h EC50 data are reported for Daphnia magna in a closed system and relationships established between EC50, solubility and octanol/water partition coefficient. It is suggested that when presenting QSAR data, logarithmic plots should be prepared of the toxic concentration versus both solubility and octanol/water partition coefficient. The results indicate that in this case the toxic effect is nonspecific in nature and that the EC50 is controlled primarily by organism/water partitioning.

[1]  H. Könemann.  Quantitative structure-activity relationships in fish toxicity studies. Part 1: relationship for 50 industrial pollutants. , 1981, Toxicology.

[2]  G. LeBlanc.  Acute toxicity of priority pollutants to water flea (Daphnia magna) , 1980, Bulletin of environmental contamination and toxicology.

[3]  P. Gross,et al.  THE SOLUBILITIES OF CERTAIN SLIGHTLY SOLUBLE ORGANIC COMPOUNDS IN WATER , 1931 .

[4]  W. Shiu,et al.  Determination of air-water Henry's law constants for hydrophobic pollutants , 1979 .

[5]  Milton Manes,et al.  Partitioning of organic compounds in octanol-water systems , 1982 .

[6]  W. Shiu,et al.  Acute toxicity of fresh and weathered crude oils to , 1983 .

[7]  R. Koch.  Ökotoxikologische Stoffbewertung und strukturchemische Parameter , 1982 .

[8]  O. Hutzinger,et al.  Reversed-phase thin-layer chromatography of polynuclear aromatic hydrocarbons and chlorinated biphenyls , 1982 .

[9]  D. T. Boyles.  Toxicity of Hydrocarbons and Their Halogenated Derivatives in an Aqueous Environment , 1980 .

[10]  J. Carey,et al.  The environmental significance of surface films: Part 1—octanol-water partition coefficients for DDT and hexachlorobenzene , 1982 .

[11]  Gilman D. Veith,et al.  Structure–Toxicity Relationships for the Fathead Minnow, Pimephales promelas: Narcotic Industrial Chemicals , 1983 .

[12]  M. D'Amboise,et al.  Hydrophobicity and Retention in Reversed Phase Liquid Chromatography , 1982 .

[13]  Gilman D. Veith,et al.  A rapid method for estimating log P for organic chemicals , 1979 .

[14]  D. Crisp,et al.  Narcotic and toxic action of organic compounds on barnacle larvae , 1967 .

[15]  Guo-lan Huang,et al.  Determination and interpretation of hydrocarbon toxicity to ciliate protozoa , 1983 .

[16]  M. Vighi,et al.  Toxicity of selected chlorobenzenes to aquatic organisms , 1983 .

[17]  H. Könemann,et al.  Determination of log Poct values of chloro-substituted benzenes, toluenes and anilines by high-performance liquid chromatography on ODS-silica , 1979 .

[18]  W. F. Spencer,et al.  Hexachlorobenzene: Its Vapor Pressure and Vapor Phase Diffusion in Soil , 1980 .

[19]  D. H. Freeman,et al.  Determination of the solubility behavior of some polycyclic aromatic hydrocarbons in water , 1978 .

[20]  Sujit Banerjee,et al.  Water solubility and octanol/water partition coefficients of organics. Limitations of the solubility-partition coefficient correlation , 1980 .

[21]  Samuel H. Yalkowsky,et al.  Estimation of Entropies of Fusion of Organic Compounds , 1979 .

[22]  C. Tran,et al.  An approach to the prediction of retention times in liquid chromatography , 1981 .

[23]  W. Shiu,et al.  Vapor-pressure correlations for low-volatility environmental chemicals , 1982 .

[24]  D Mackay,et al.  Three-parameter equation describing the uptake of organic compounds by fish. , 1984, Environmental science & technology.

[25]  Samuel H. Yalkowsky,et al.  Relationships between aqueous solubility and octanol-water partition coefficients , 1980 .

[26]  H. Watarai,et al.  Determination of partition coefficients of halobenzenes in heptane/water and 1-octanol/water systems and comparison with the scaled particle calculation , 1982 .

[27]  C. Ruepert,et al.  Quantitative structure-activity relationships for polycyclic aromatic hydrocarbons: Correlation between molecular connectivity, physico-chemical properties, bioconcentration and toxicity in Daphnia pulex , 1984 .

[28]  L. J. Mullins,et al.  Some Physical Mechanisms in Narcosis. , 1954 .

[29]  K. Kaiser.  A non-linear function for the approximation of octanol/water partition coefficients of aromatic compounds with multiple chlorine substitution , 1983 .

[30]  W. Shiu,et al.  A predictive correlation for the acute toxicity of hydrocarbons and chlorinated hydrocarbons to the water flea () , 1983 .

[31]  W. Shiu,et al.  The Correlation of the Toxicity to Algae of Hydrocarbons and Halogenated Hydrocarbons with their Physical-Chemical Properties , 1980 .

[32]  L. Andrews,et al.  Cation Complexes of Compounds Containing Carbon-Carbon Double Bonds. VI. The Argentation of Substituted Benzenes , 1950 .

[33]  Yadu B. Tewari,et al.  AQUEOUS SOLUBILITIES, OCTANOL WATER PARTITION-COEFFICIENTS, AND ENTROPIES OF MELTING OF CHLORINATED BENZENES AND BIPHENYLS , 1984 .

[34]  John Ferguson,et al.  The Use of Chemical Potentials as Indices of Toxicity , 1939 .

[35]  K. Verschueren.  Handbook of environmental data on organic chemicals , 1977 .

[36]  Samuel H. Yalkowsky,et al.  Solubility and Partitioning. 3. The Solubility of Halobenzenes in Water , 1979 .

[37]  D Mackay,et al.  Correlation of bioconcentration factors. , 1982, Environmental science & technology.

[38]  R. D. Wauchope,et al.  Temperature dependence of solubilities in water and heats of fusion of solid aromatic hydrocarbons , 1972 .

[39]  W. Shiu,et al.  A critical review of Henry’s law constants for chemicals of environmental interest , 1981 .

[40]  C. L. De Ligny,et al.  CORRELATIONS BETWEEN LIQUID CHROMATOGRAPHIC CAPACITY RATIO DATA ON LICHROSORB RP-18 AND PARTITION COEFFICIENTS IN THE OCTANOL-WATER SYSTEM , 1982 .

[41]  A. Leo,et al.  Substituent constants for correlation analysis in chemistry and biology , 1979 .

[42]  B. McDuffie,et al.  Estimation of octanol/water partition coefficients for organic pollutants using reverse-phase HPLC , 1981 .