Comparative properties of N-acetyl derivatives of oxime N-methylcarbamates and aryl N-methylcarbamates as insecticides and acetylcholinesterase inhibitors

N-acylation of aryl N-methylcarbamates is known to reduce their mammalian toxicity considerably without adversely affecting their insecticidal activity. It has now been found that N-acylation of several insecticidal oxime carbamates results in loss of toxicity both to insects and mammals. Kinetic data for base-catalysed solvolysis and inhibition of acetylcholinesterase, together with published work on metabolism, are combined to provide a rationale for this unexpected observation and to account for the selective toxicity of aryl N-acetyl-N-methylcarbamates.