Identification and synthesis of the sex pheromone of the Madeira mealybug, Phenacoccus madeirensis Green.
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.
Ho
Hsiao-Yung
HY
Institute of Cellular and Organismic Biology, Academia Sinica, Taipei, Taiwan, 11526, Republic of China. shine@gate.sinica.edu.tw
Su
Yu-Ting
YT
Ko
Chi-Hung
CH
Tsai
Ming-Yu
MY
D000818:Animals; D002087:Butyrates / Q000138:chemical synthesis / Q000302:isolation & purification / Q000494:pharmacology*; D005260:Female; D008401:Gas Chromatography-Mass Spectrometry; D006430:Hemiptera / Q000502:physiology*; D008297:Male; D008968:Molecular Conformation; D012724:Sex Attractants / Q000138:chemical synthesis / Q000302:isolation & purification / Q000494:pharmacology*; D012726:Sexual Behavior, Animal / Q000187:drug effects; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis / Q000302:isolation & purification / Q000494:pharmacology*
C488424:2-isopropenyl-5-methyl-4-hexenyl 2-methylbutanoate; D002087:Butyrates; D012724:Sex Attractants; D013729:Terpenes; C543647:chrysanthemyl 2-methylbutanoate