EPOXIDIZED HYDROCARBON ACID ESTERS HAVING JUVENILE HORMONE ACTIVITY

摘要

A process is disclosed herein for the preparation of hydrocarbon acid esters of formula, IN WHICH R1 and R2 are alkyl groups containing two to four carbon atoms or R1 and R2 together are a polymethylene group containing four to five carbon atoms forming a cyclopentane or cyclohexane ring, R3, R4 and R5 are alkyl groups containing 1 - 2 carbon atoms and Z1 and Z2 together are a carbon-carbon double bond or an epoxide; whereby the appropriate ketone of formula R1R2C = O is condensed with the ylid generated from either 4-oxopentyl-1-triphenylphosphonium iodide ethylene ketal or 4-oxohexyl-1-triphenylphosphonium iodide ethylene ketal, followed by acid treatment to remove the ketal, and yield the appropriate ketonic intermediate, which is treated successively with either of the preceding ylids and then acid treatment to yield a ketone of formula R1R2C = CHCH2CH2CR3 = CHCH2CH2COR4; the last said compound is then treated with the anion prepared from a dialkylcarbomethoxymethyl or a dialkylcarboethoxymethyl phosphonate to yield the hydrocarbon acid esters of the above formula in which Z1 and Z2 together are a carbon-carbon double bond, said last compounds are oxidized to yield the hydrocarbon acid esters of the above formula in which Z1 and Z2 together are an epoxide. The hydrocarbon acid esters of this invention are useful for the control of insect populations and methods for their formulation and use for this purpose are given.