AbstractA new series of substituted 2‐anilino‐3‐methylbutyrates has been prepared; bioassay data for these compounds onHeliothis virescens, Musca domestica, Aphis fabaeandTetranychus urticaeare presented and discussed. Some unexpected relationships were observed between the nature of the substituents and the biological activity. Increases in foliar stability were noted with certain substitution patterns. Both α‐cyano‐3‐phenoxybenzyl 3‐methyl‐2‐(α, α, α,2‐tetrafluoro‐p‐toluidino)butyrate and the corresponding 2‐(2‐chloro‐α, α, α‐trifluoro‐p‐toluidino)‐3‐methylbutyrate showed good stability in air and light, and exhibited biological activities of a similar nature and potency to those of previously known synthetic pyrethroids. Esters of the (R)‐2‐ anilino‐3‐methylbutyric acids are far more active than those prepared from the (S)‐enantiomers. The (R)‐configuration at C‐2 in these acids is sterically equivalent to the active absolute configuration at the chiral carbon α to the carboxylate group in both the permethrin and the fenvalerate types of pyrethroids. A new class of insecticidal 2‐(isoindolin‐2‐yl)alkanoates is also reported. In this series the most biologically active analogue was α‐cyano‐3‐phenoxybenzyl 3‐methyl‐2‐(4,5,6,7‐tetrafluoroisoindolin‐2‐yl)butyrate. These esters were considerably less stable than the anilino analogues on exposure to air and light.

Henrick, C. A., Garcia, B. A., Staal, G. B., Cerf, D. C., Anderson, R. J., Gill, K., Chinn, H. R., Labovitz, J. N., Leippe, M. M., Woo, S. L., Carney, R. L., Gordon, D. C., & Kohn, G. K. (1980). 2‐anilino‐3‐methylbutyrates and 2‐(isoindolin‐2‐yl)‐3‐methylbutyrates, two novel groups of synthetic pyrethroid esters not containing a cyclopropane ring. Pesticide Science, 11(2), 224–241. Portico.