ABSTRACT
Two compounds (trans-1R,3R-chrysanthemyl R-2-methylbutanoate and R-lavandulyl R-2-methylbutanoate) identified from aeration extracts of virgin female Madeira mealybug, Phenacoccus madeirensis Green (Hemiptera: Pseudococcidae), were synthesized and tested in field bioassays in northern Taiwan over a 1-mo period. In total, 1,492 male P. madeirensis were captured in sticky traps. Our results showed that 1 microg of synthetic trans-1R,3R-chrysanthemyl R-2-methylbutanoate released from a plastic tube dispenser was attractive to the mealybugs. Different stereoisomers of chrysanthemyl 2-methylbutanoate also were tested. The insect-produced stereoisomer was the most attractive of all the isomers tested, and the stereochemistry of the acid moiety proved to be more critical than that of the alcohol moiety. The minor component found in extracts, R-lavandulyl R-2-methylbutanoate, alone was not attractive to male Madeira mealybugs nor did it act synergistically or additively with the main component.
Subject(s)
Hemiptera/chemistry , Hemiptera/physiology , Sex Attractants/chemistry , Sex Attractants/pharmacology , Animals , Butyrates/chemistry , Butyrates/pharmacology , Female , Insect Control , Male , Stereoisomerism , Taiwan , Terpenes/chemistry , Terpenes/pharmacologyABSTRACT
Two components were identified from aeration extracts of the virgin female Madeira mealybug, Phenacoccus madeirensis as trans-(1R,3R)-chrysanthemyl (R)-2-methylbutanoate and (R)-lavandulyl (R)-2-methylbutanoate (with a ratio of 3:1) by a combination of gas chromatography retention time matches, mass spectrometry, and microchemical tests. The structures and chirality of the compounds were confirmed by comparing with synthetic compounds. The synthetic trans-(1R,3R)-chrysanthemyl (R)-2-methylbutanoate was highly attractive to males in laboratory bioassays; the synthetic (R)-lavandulyl (R)-2-methylbutanoate was weakly attractive. No synergistic effect was observed when the mixture of the two compounds was tested.
