BACKGROUND: Feeding deterrent activity of synthetic halogen lactones against larvae and adults of the lesser mealworm, Alphitobius diaperinus Panzer, in laboratory choice and no-choice tests was studied. The compounds were synthesised from racemic and enantiomerically enriched (ee = 91-98%) cis- and trans-piperitols, which were obtained from (±)-piperitone. RESULTS: Structure-activity relationship studies identified several synthetic halolactones with a very strong feeding deterrent activity. The most active were the enantiomeric chlorolactones with chiral centre configurations (1S,4S,5R,6R) and (1R,4R,5S,6S) and their racemic mixture. The racemic bromo- and iodolactones obtained from cis-piperitol and saturated lactones with a chiral centre configuration (1R,4S,6R) were also very good antifeedants in comparison with piperitone. Most of the studied compounds were better antifeedants against adults than against larvae-among the 21 compounds, only one bromolactone with a chiral centre configuration (1S,4R,5R,6R) was a weaker deterrent for adults. CONCLUSION: Chemical transformation of the piperitone molecule by the introduction of a lactone function and a halogen atom strongly changed its antifeedant properties against the lesser mealworm. Optimum activity is dependent on the presence of a chlorine atom at C-5 of the cyclohexane ring. The activity of bromo- and iodolactones depended strongly on the chiral centre configuration and the halogen substituent.
BACKGROUND: Feeding deterrent activity of synthetic halogenlactones against larvae and adults of the lesser mealworm, Alphitobius diaperinus Panzer, in laboratory choice and no-choice tests was studied. The compounds were synthesised from racemic and enantiomerically enriched (ee = 91-98%) cis- and trans-piperitols, which were obtained from (±)-piperitone. RESULTS: Structure-activity relationship studies identified several synthetic halolactones with a very strong feeding deterrent activity. The most active were the enantiomeric chlorolactones with chiral centre configurations (1S,4S,5R,6R) and (1R,4R,5S,6S) and their racemic mixture. The racemic bromo- and iodolactones obtained from cis-piperitol and saturated lactones with a chiral centre configuration (1R,4S,6R) were also very good antifeedants in comparison with piperitone. Most of the studied compounds were better antifeedants against adults than against larvae-among the 21 compounds, only one bromolactone with a chiral centre configuration (1S,4R,5R,6R) was a weaker deterrent for adults. CONCLUSION: Chemical transformation of the piperitone molecule by the introduction of a lactone function and a halogen atom strongly changed its antifeedant properties against the lesser mealworm. Optimum activity is dependent on the presence of a chlorine atom at C-5 of the cyclohexane ring. The activity of bromo- and iodolactones depended strongly on the chiral centre configuration and the halogen substituent.