Predicting the toxicity of substituted phenols to aquatic species and its changes in the stream and effluent waters

Abstract

The changes in the acute toxicity of 16 phenols toward Selenastrum capricornutum and Daphnia magna were examined as a function of their physical/chemical properties. The results demonstrated that phenols with a higher octanol-water partition coefficient (K-ow) had a higher toxicity toward aquatic organisms. The toxicity of phenols was closely related to the log K-ow values, with correlation coefficients of 0.93 (except for the nitrophenols) and 0.89 for S. capricornutum and D. magna, respectively. The changes in the phenols toxicities in the site waters (i.e., stream and effluent waters) were investigated by calculating the water effect ratios (WER) from the results of the toxicity tests in the site waters using D. magna. The results showed that the degree of ionization for each phenolic compound was altered by the differences in the dissociation constant (pK(a)), and the change in the toxicity could be predicted. Therefore, the WER should be considered when the toxicity of phenolic compounds is estimated in site waters. The quantitative structure-activity relationships (QSAR) study showed that the toxicity of the phenols to D. magna could be predicted by the hydrophobicity (log K-ow) alone and by combining the log K-ow with pK(a), while the toxicity to S. capricornutum was predicted by a combination of hydrophobicity (log K-ow) and E-LUMO (or pK(a)).