Steric, electronic, and polar parameters that affect the toxic actions of O-alkyl, O-phenyl phosphonothionate insecticides

Add time:07/12/2019    Source:sciencedirect.com

The toxic action of a series of O-alkyl, O-substituted-phenyl alkyl- and aryl-phosphonates and phosphonothionates have been evaluated by correlating the linear free energy parameters for steric (Es), electronic (σ), and polar (σ∗) effects with topical LD50 to the house fly and oral LD50 to the white mouse. In molecules free from major steric interactions with the reactive P atom, variations in these linear free energy parameters account for >90% of the variations in the LD50 values, and the degree of correlation with LD50 is at least as precise as that with the biomolecular rate constants for inhibition of the target-site enzyme acetylcholinesterase. The value of correlations of linear free energy parameters with LD50 in understanding quantitative structure-activity relationships is illustrated.

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