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.
USDA, Agricultural Research Service, National Center for Agricultural Utilization Research, IL 61604, USA. bartelrj@ncaur.usda.gov
Robert J
RJ
Bartelt
Allard A
AA
Cossé
Bruce W
BW
Zilkowski
David
D
Weisleder
Stephen H
SH
Grode
Robert N
RN
Wiedenmann
Susan L
SL
Post
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