Piperonyl ethers having juvenile hormone mimetic activity

#1. Field

#The present invention is concerned with piperonyl ethers that have juvenile hormone mimetic activity. More particularly, it is concerned with straight chain .omega.-monounsaturated alkenyl, .omega.-haloalkyl, .omega.-hydroxyalkyl, .omega.-epoxyalkyl, .omega.-alkoxyalkyl, .omega.-alkylthioalkyl, .omega.-acylalkyl and .omega.-carbamoylalkyl piperonyl ethers.

#2. Prior Art

#The compounds of the present invention may be more fully understood by reference to the following examples.

#Piperonol, 15.2 g. (0.1 mole), was dissolved in 200 ml. of dimethoxyethane. To this solution there was added 4.8 g. (0.1 mole) of sodium hydride. The resulting mixture was refluxed for 30 minutes after which 27.2 g. (0.1 mole) of 1,8-dibromooctane and a crystal of iodine were added. This mixture was then refluxed for 24 hours. At the end of this time, the mixture was cooled and mixed with an equal amount of water. Then a like amount of dichloromethane was added and the two layers were separated. The organic layer was dried and evaporated. The crude product obtained in this way was purified by passing through a silica gel chromatography column using a 5% ether in hexane eluent. In this way there was obtained 13 g. of oily 8-bromooctyl piperonyl ether. The NMR spectra was consistent with the assigned structure. An infrared spectra had strong adsorptions at 3.4, 3.5, 6.7, 6.95, 8.0, 9.1, 9.6, 10.7 and 12.3 microns. Analysis was as follows:

#Calculated Found ______________________________________ Br % 23.3 23.3 ______________________________________