Abstract
Acute 12 h and 24 h lethal toxicity (12 h-LC 50 and 24 h-LC 50) of 31 substituted phenols to Rana japonica tadpoles was determined. Results indicate that toxicity of phenols to tadpoles varied only slightly with length of exposure and the 12-h test could serve as surrogate of the 24-h test. A mechanism-based quantitative structure–activity relationship (QSAR) method was employed and 1-octanol/water partition coefficient (log K ow)-dependent models were developed to study different modes of toxic action. Most phenols elicited their response via a polar narcotic mechanism and an excellent log K ow-dependent model was obtained. Soft electrophilicity and pro-electrophilicity were observed for some phenols and a good log K ow-dependent model was also achieved. Additionally, the significant dissociation of carboxyl on benzoic acid derivatives sharply reduced their toxicity. A statistically robust QSAR model was developed for all studied compounds with the combined application of log K ow, energy of lowest unoccupied orbital ( E lumo), heat of formation (HOF) and the first-order path molecular connectivity dices ( 1χ p ) .
Published Version
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