Investigations into carbamate insecticide selectivity: I: Evaluation of potential selectophores

In an effort to improve the generally unfavorable mouse/housefly toxicity ratio of most carbamate insecticides, potential selectophores (nitrile, carbamoyl oxime, carboxylic ester, or amide) were incorporated into a series of phenyl N-methylcarbamates. In addition to the insect and mouse toxicity determinations, the anticholinesterase activity of these compounds was determined for purified housefly head acetylcholinesterase and bovine erythrocyte acetylcholinesterase. The presence of these functional groups, in general, did not give enhanced selectivity ratios and, in one case, (o-N-methylcarbamoyloxyiminomethylphenyl N-methylcarbamate), a very unfavorable selectivity ratio of <0.03 was obtained. A mechanism implicating a Beckmann rearrangement is advanced to rationalize the high rodenticidal activity of this molecule. In general, the carbamates showed poor insecticidal activity when applied alone to the housefly, but, when the flies were pretreated with piperonyl butoxide, the compounds were quite toxic. Finally, an explanation is derived which seeks to justify the inability of these potential selectophores to improve the mouse/housefly toxidity ratio.