Identification and Synthesis of a Female-Produced Sex Pheromone for the Cerambycid Beetle Prionus Californicus

• Published in: Journal of chemical ecology 2009-05, Vol.35 (5), p.590-600
• Main Authors: Rodstein, Joshua, McElfresh, J. Steven, Barbour, James D, Ray, Ann M, Hanks, Lawrence M, Millar, Jocelyn G
• Format: Article
• Language: English
• Subjects: Agriculture; Animal and plant ecology; Animal, plant and microbial ecology; Animals; antennae; Autoecology; Bioassays; Biochemistry; Biological and medical sciences; Biological Microscopy; Biomedical and Life Sciences; Cerambycidae; Chemical ecology; chemical structure; Chemical synthesis; Coleoptera - chemistry; Control; Decanoic Acids - analysis; Decanoic Acids - chemical synthesis; Decanoic Acids - isolation & purification; Ecology; electroantennography; electrophysiology; Entomology; Female; females; Fibers; Fundamental and applied biological sciences. Psychology; Gas chromatography; Gas Chromatography-Mass Spectrometry; Hops; Insects; Integrated pest control; Isomerism; isomers; Life Sciences; Mass spectrometry; Pests; Pheromones; Phytopathology. Animal pests. Plant and forest protection; Prionus; Prionus californicus; Protozoa. Invertebrata; Protozoa. Invertebrates; sex attractants; Sex Attractants - analysis; Sex Attractants - chemical synthesis; Sex Attractants - isolation & purification; sex pheromones; Solid Phase Microextraction; synthesis
• ISSN: 0098-0331; 1573-1561
• DOI: 10.1007/s10886-009-9623-7

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.