Dimethylfuran-lactone pheromone from males of Galerucella calmariensis and Galerucella pusilla.
Male Galerucella calmariensis and Galerucella pusilla (Coleoptera: Chrysomelidae) emit an aggregation pheromone while feeding on host foliage. Isolation of the compound from collected volatiles was guided by comparisons of gas chromatograms of extracts from males and females and by gas chromatography-electroantennographic detection. The compound was identified by a combination of spectrometric methods and microchemical tests as the novel dimethylfuran lactone, 12,13-dimethyl-5,14-dioxabicyclo[9.2.1]tetradeca-1(13),11-dien-4-one. The structure was confirmed by synthesis, and the synthetic compound attracted males and females of both species in field bioassays. These beetles were previously introduced into North America as biological control agents for the invasive wetland weed, purple loosestrife Lythrum salicaria, and the pheromone could become a tool for monitoring populations. A new method is described for distinguishing the two species based on the tibial spurs of the males.
Bartelt
Robert J
RJ
USDA, Agricultural Research Service, National Center for Agricultural Utilization Research, IL 61604, USA. bartelrj@ncaur.usda.gov
Cossé
Allard A
AA
Zilkowski
Bruce W
BW
Weisleder
David
D
Grode
Stephen H
SH
Wiedenmann
Robert N
RN
Post
Susan L
SL
D000818:Animals; D001517:Coleoptera / Q000737:chemistry* / Q000187:drug effects; D005260:Female; D005663:Furans / Q000737:chemistry*; D006865:Hydrogenation; D007783:Lactones / Q000737:chemistry*; D008297:Male; D013058:Mass Spectrometry; D008832:Microchemistry; D019906:Nuclear Magnetic Resonance, Biomolecular; D009822:Oils, Volatile / Q000032:analysis; D010675:Pheromones / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D013056:Spectrophotometry, Ultraviolet
D005663:Furans; D007783:Lactones; D009822:Oils, Volatile; D010675:Pheromones; C515369:dimethylfuran-lactone