Allethrin

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Abstract
Synthetic work leading to the commercial preparation of allethrin (the ester of (±)‐cis‐trans‐3‐isobutenyl‐2 : 2‐dimethylcyclopropane‐1‐carboxylic acid [(±)‐cis‐trans‐chrys‐anthemic acid] with (±)‐2‐allyl‐3‐methylcyclopent‐2‐en‐4‐ol‐1‐one [(±)‐allethrolone]} is reviewed briefly. The relative insecticidal activity and abundance of the eight isomeric esters present in allethrin are deduced and the most effective is shown to be (+)‐allethronyl (+)‐trans‐chrysanthemate. The effect of various changes in the molecule of allethrin on insecticidal activity is described. The biological action of allethrin appears to be of a similar nature to that of the natural pyrethrins, and is associated with the particular stereochemical conformation in which the various parts of the molecule are held with respect to each other and with the chemical and physical properties of the groups so positioned. Although allethrin is inferior to the natural pyrethrins against most species of insects and by most methods of application, it is highly biologically active and, unlike many modern synthetic insecticides, has, so far, been found harmless to mammals.

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