Question

The active ingredient in some insect repellents is N,N-diethyl-m-toluamide. How does this
insect repellent work? Which carboxylic acid and amine would be released by the hydrolysis of
this amide? Is this important?

Answer 1

The hydrolysis of  N,N-diethyl-m-toluamide yields 3-methylbenzoic acid which easily biodegradable.

The insecticide repellent N,N-diethyl-m-toluamide is used to repel rather than kill insects. It functions by interfering with the ability of the insects to detect body heat and skin chemicals. In a nutshell, it confuses the receptors in the insect.

The hydrolysis of N,N-diethyl-m-toluamide  yields 3-methylbenzoic acid and diethylamine as the products. This is important because the 3-methylbenzoic acid is not an environmental concern since it is readily biodegradable and does not accumulate significantly in living organisms. It has also not been found to be mobile in soil and water. Environmental concerns are always a prime consideration in assessing chemicals for use.

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