Kinetics and mechanism of the nucleophilic displacement reactions of chloroacetanilide herbicides: investigation of alpha-substituent effects.

The ease with which alpha-chloroacetanilide herbicides undergo displacement reactions with strong nucleophiles, and their recalcitrance toward weak ones, is intimately related to their herbicidal properties and environmental chemistry. In this study, we investigate the kinetics and mechanisms of nucleophilic substitution reactions of propachlor and alachlor in aqueous solution. The role played by the alpha-amide group was examined by including several structurally related analogs of propachlor possessing modified alpha substituents.