Design of Novel Insect Anti Juvenile Hormones: Allylic Alcohol Derivatives

Three analogues of 3,3-dimethyl-2-propenol (dimethylallyl alcohol) were synthesized and found to possess anti juvenile hormone activity when assayed on lepidopterous insect species (particularly the tobacco hornworm, Manduca sexta). The most active compound of those described, 3,3-dichloro-2-propenyl hexanoate, caused precocious metamorphosis, inhibited juvenile hormone (JH) biosynthesis in vitro, and reduced JH titers in vivo.