TY - JOUR
T1 - Identification and synthesis of a Female-produced sex pheromone for the cerambycid beetle prionus californicus
AU - Rodstein, Joshua
AU - McElfresh, J. Steven
AU - Barbour, James D.
AU - Ray, Ann M.
AU - Hanks, Lawrence M.
AU - Millar, Jocelyn G.
N1 - Funding Information:
Acknowledgements We thank Wittko Francke for valuable discussions with regard to mass spectral interpretation, Ian Wright, Ian Swift, and David Stives for technical assistance, and Michael Long and the Los Angeles County Department of Parks and Recreation for permission to conduct research at Placerita Canyon Natural Area. This project was supported by the USDA Western Regional IPM Center, awards #2003-51120-02098 and #2007-34103-18495, and the National Research Initiative of the USDA Cooperative State Research, Education and Extension Service, grant number #2006-35302-17457 (to JGM, JDB, LMH), and the Alphawood Foundation (to LMH).
PY - 2009/5
Y1 - 2009/5
N2 - Females of the large cerambycid beetle Prionus californicus produce a powerful sex pheromone that attracts males. The pheromone was adsorbed on solid phase microextraction (SPME) fibers inserted into the ovipositor sheath and analyzed by coupled gas chromatography-electroantennogram detection and GC-mass spectrometry. The pheromone was identified as an isomer of 3,5- dimethyldodecanoic acid by a combination of retention index comparisons and mass spectral interpretation. The mass spectrum was misleading because it exhibited enlarged fragment ions that were not representative of branch points or other obvious stabilizing structural elements. The structure was verified by synthesis of 3,5-dimethyldodecanoic acid as a mixture of all four possible isomers, and this mixture was highly attractive to male beetles in field bioassays. The SPME extracts also contained several other compounds that were tentatively identified as chain-extended homologs of the main pheromone component. This pheromone should prove useful for sampling and management of the beetle, which is an important pest of hops, and an occasional pest in a variety of orchard crops. Although this is the first female-produced pheromone to be identified from the Cerambycidae, there is considerable evidence for pheromone production by females of other species in the subfamily Prioninae. Thus, this pheromone and the associated methodology used in its identification should be useful in the identification of female-produced attractant pheromones from other members of the subfamily.
AB - Females of the large cerambycid beetle Prionus californicus produce a powerful sex pheromone that attracts males. The pheromone was adsorbed on solid phase microextraction (SPME) fibers inserted into the ovipositor sheath and analyzed by coupled gas chromatography-electroantennogram detection and GC-mass spectrometry. The pheromone was identified as an isomer of 3,5- dimethyldodecanoic acid by a combination of retention index comparisons and mass spectral interpretation. The mass spectrum was misleading because it exhibited enlarged fragment ions that were not representative of branch points or other obvious stabilizing structural elements. The structure was verified by synthesis of 3,5-dimethyldodecanoic acid as a mixture of all four possible isomers, and this mixture was highly attractive to male beetles in field bioassays. The SPME extracts also contained several other compounds that were tentatively identified as chain-extended homologs of the main pheromone component. This pheromone should prove useful for sampling and management of the beetle, which is an important pest of hops, and an occasional pest in a variety of orchard crops. Although this is the first female-produced pheromone to be identified from the Cerambycidae, there is considerable evidence for pheromone production by females of other species in the subfamily Prioninae. Thus, this pheromone and the associated methodology used in its identification should be useful in the identification of female-produced attractant pheromones from other members of the subfamily.
KW - 3,5-dimethyldodecanoic acid
KW - 3,5-dimethylpentadecanoic acid
KW - 3,5-dimethyltridecanoic acid
KW - Cerambycidae
KW - Coleoptera
KW - Prioninae
UR - http://www.scopus.com/inward/record.url?scp=67349131279&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=67349131279&partnerID=8YFLogxK
U2 - 10.1007/s10886-009-9623-7
DO - 10.1007/s10886-009-9623-7
M3 - Article
C2 - 19396491
AN - SCOPUS:67349131279
VL - 35
SP - 590
EP - 600
JO - Journal of Chemical Ecology
JF - Journal of Chemical Ecology
SN - 0098-0331
IS - 5
ER -