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Pine-feeding bark beetles (Coleoptera: Scolytidae) interact chemically with their host pines (Coniferales: Pinaceae) via the behavioral, physiological, and biochemical effects of one class of isoprenoids, the monoterpenes and their derivatives. Pine monoterpenes occur in the oleoresin and function as behaviorally active kairomones for pine bark beetles and their predators, presenting a classic example of tritrophic chemical communication. The monoterpenes are also essential co-attractants for pine bark beetle aggregation pheromones. Ironically, pine monoterpenes are also toxic physiologically to bark beetles at high vapor concentrations and are considered an important component of the defense of pines. Research over the last 30 years has demonstrated that some bark beetle aggregation pheromones arise through oxygenation of monoterpenes, linking pheromone biosynthesis to the host pines. Over the last 10 years, however, several frequently occurring oxygenated monoterpene pheromone components (e.g., ipsenol, ipsdienol and frontalin) have also been shown to arise through highly regulated de novo pathways in the beetles (reviewed in Seybold and Tittiger, 2003). The most interesting nexus between these insects and their plant hosts involves the latestage reactions in the monoterpenoid biosynthetic pathway, during which isomeric dimethylallyl diphosphate and isopentenyl diphosphate are ultimately elaborated to stereospecific monoterpenes in the trees and to hydroxylated monoterpenes or bicyclic acetals in the insects. There is signal stereospecificity in both production of and response to the monoterpenoid aggregation pheromones of bark beetles and in response to the monoterpenes of the pines. In the California fivespined ips, Ips paraconfusus, we Dedicated to Professor David L. Wood on the occasion of his 75th birthdayÓ Springer Science+Business Media B.V. 2006have discovered a number of cytochome P450 genes that have expression patterns indicating that they may be involved in detoxifying monoterpene secondary metabolites and/or biosynthesizing pheromone components. Both processes result in the production of oxygenated monoterpenes, likely with varying degrees of stereospecificity. A behavioral analysis of the stereospecific response of I. paraconfusus to its pheromone is providing new insights into the development of an efficacious bait for the detection of this polyphagous insect in areas outside the western United States. In contrast, a Eurasian species that has arrived in California, the Mediterranean pine engraver, Orthotomicus (Ips) erosus, utilizes both a monoterpenoid (ipsdienol) and a hemiterpenoid (2-methyl-3-buten-2-ol) in its pheromone blend. The stereospecificity of the response of O. erosus to the monoterpenoid appears to be the key factor to the improved potency of the attractant bait for this invasive species.

This review summarizes the literature related to the chemical ecology of the Cerambycidae and provides a brief overview of cerambycid biology, ecology, economic significance, and management. Beetles in the family Cerambycidae have assumed increasing prominence as pests of forest and shade trees, shrubs, and raw wood products, and as vectors of tree diseases. Exotic species associated with solid wood packing materials have been notable tree killers in North American urban and peri-urban forests. In forested ecosystems native species respond to disturbances such as fires and windstorms, and initiate the biodeterioration of woody tissue. Eggs are laid by females, on or through the bark surface of stem and branch tissue of moribund, recently killed or decomposing woody plants; larval cerambycids (roundheaded woodborers) typically feed in the phloem and later in the xylem. Females will also, in some cases, select living hosts, e.g. adult conifer and angiosperm trees, for oviposition. Research on the chemical ecology of over 70 species has revealed many examples of attractive kairomones (such as floral volatiles, smoke volatiles, trunk and leaf volatiles, and bark beetle pheromones), repellents and deterrents, oviposition stimulants, short-and long-range sex pheromones, and defensive substances. Emerging generalities are that attractants tend to be monoterpenoids and phenolic esters; oviposition stimulants are monoterpenoids and flavanoids; short-range sex pheromones are femaleproduced, methyl-branched cuticular hydrocarbons; and long-range sex pheromones are male-produced α-hydroxy ketones and (α,β)-diols ranging in length from 6 to 10 carbons. The latter compounds appear to originate from glands in the male thorax; putative defensive substances originate from metasternal secretory pores or mandibular glands. In one unusual case, a flightless, subterranean female that attacks sugar cane produces a sex pheromone that is derived from the amino acid isoleucine. With significantly more than 35,000 species of Cerambycidae worldwide, these generalities will be subject to change as more species are examined.

Thirty-five populations ofIps pini (Say) and one population each ofIps avulsus (Eichhoff) andIps bonanseai (Hopkins) were analyzed for the enantiomeric composition of ipsdienol (2-methyl-6-methylene-2,7-octadien-4-ol). Populations ofI. pini occur as at least two distinct regional pheromone variants: New York type [32%-(-) to 56%-(-)-ipsdienol] and California type [94%-(-) to 98%-(-)-ipsdienol]. A third phenotype may occur in southeastern British Columbia, Idaho, and Montana [91%-(-) to 95%-(-)], possibly indicating a zone of hybridization. Populations of the New York type occur in southwestern British Columbia, Alberta, Saskatchewan, Minnesota, and Wisconsin suggesting a continuum through the Canadian provinces and Lake States. The presence of the New York type in western Canada is likely linked to the Quaternary history of the transcontinentally distributed host,Pinus banksiana Lamb. MaleI. avulsus [∼25%-(-)] and maleI. bonanseai [-29%-(-)] both produce ipsdienol, but not ipsenol. Production of ipsdienol by maleI. pini was evaluated in six differentPinus spp. hosts. Following transfer of maleI. pini to hosts other than the host of origin, the percentage of the (-)-enantiomer of ipsdienol declined when compared to production in the host of origin.