(2S,4E)-2-Hydroxy-4-octen-3-one, a Male-Produced Attractant Pheromone of the Cerambycid Beetle Tylonotus bimaculatus

We report the identification of a novel pheromone structure from males of the cerambycid beetle Tylonotus bimaculatus Haldeman (Cerambycinae: Hesperophanini), a species native to eastern North America. Volatiles collected from adult males contained (2S,4E)-2-hydroxyoct-4-en-3-one (71 %), (3R,4E)-3-h...

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Bibliographic Details
Published in:Journal of chemical ecology 2015-07, Vol.41 (7), p.670-677
Main Authors: Zou, Yunfan, Millar, Jocelyn G, Blackwood, J. Scott, Van Duzor, Ryan, Hanks, Lawrence M, Mongold-Diers, Judith A, Wong, Joseph C. H, Ray, Ann M
Format: Article
Language:English
Subjects:
adults
Agriculture
Animals
bioassays
Biochemistry
Biological Microscopy
Biomedical and Life Sciences
Cerambycidae
Chemical ecology
Chemosensory perception
Coleoptera - chemistry
Coleoptera - metabolism
Ecology
Entomology
Female
indigenous species
Insects
Ketones - analysis
Ketones - chemical synthesis
Ketones - metabolism
Life Sciences
Male
Males
Octanols - analysis
Octanols - chemical synthesis
Octanols - metabolism
Pheromones
Sex Attractants - analysis
Sex Attractants - chemical synthesis
Sex Attractants - metabolism
Volatile Organic Compounds - analysis
Volatile Organic Compounds - chemical synthesis
Volatile Organic Compounds - metabolism
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Summary:We report the identification of a novel pheromone structure from males of the cerambycid beetle Tylonotus bimaculatus Haldeman (Cerambycinae: Hesperophanini), a species native to eastern North America. Volatiles collected from adult males contained (2S,4E)-2-hydroxyoct-4-en-3-one (71 %), (3R,4E)-3-hydroxyoct-4-en-2-one (15 %), (E)-4-octen-2,3-dione (13 %), and 2,3-octanedione (1.5 %). Four independent field bioassays with synthetic compounds confirmed that adults of both sexes were attracted by the racemate of the major component, (E)-2-hydroxyoct-4-en-3-one. No other cerambycid species were attracted in significant numbers. Attraction of both sexes is consistent with the male-produced pheromones of many other species in the subfamily Cerambycinae, but T. bimaculatus is unusual in having a pheromone chemistry that is so far unique among species in that subfamily.
ISSN:0098-0331
1573-1561
DOI:10.1007/s10886-015-0603-9