2006 Annual Report 1.What major problem or issue is being resolved and how are you resolving it (summarize project aims and objectives)? How serious is the problem? Why does it matter? Natural attractants (pheromones and host-related volatiles) will be chemically and behaviorally characterized and evaluated for practical potential in insect management. The project focuses on agriculturally important insect species for which such information is lacking or incomplete. Most of the target species belong to the large, important beetle family, Chrysomelidae, and include both pests and beneficial species: Diorhabda elongata is an introduced biocontrol agent for the invasive weedy tree, saltcedar. Galerucella calmariensis and G. pusilla are introduced biocontrol agents for the invasive wetlands weed, purple loosestrife. Flea beetles of the genera, Phyllotreta, Altica, and Epitrix are pests of crucifers and other crops, while Aphthona flea beetles are valued biocontrol agents of the weed, leafy spurge. Pheromones within the Chrysomelidae are chemically diverse but are so far very incompletely known. New synthetic methods will also be developed for pheromones of Carpophilus sap beetles, which are worldwide pests of fruits and grains. Research methodology will include: collection of airborne volatile chemicals from the insects and their hosts; chemical analysis of these; evaluation of the ability of the insect antennae to sense the compounds (using "electroantennograms"); chemical synthesis of active compounds; and characterization of their behavioral activity under field conditions. The research will lead to new practical tools for monitoring the seasonal timing, dispersal characteristics, and other population parameters for both beneficial and harmful species and for manipulating these species in ways advantageous to agriculture. Finally, the research will continue to add to the basic knowledge of beetle chemical ecology. The new information will be of value to land managers, farmers, and other scientists. This CRIS research project is aligned with National Program 304 "Crop Protection and Quarantine." Specifically, this project is relevant to Component 2 (biology of pests and natural enemies), Component 4 (pest exclusion and quarantine), Component 5 (pest control technologies), Component 6 (integrated pest management), and Component 9 (basic biology of biocontrol agents). 2.List by year the currently approved milestones (indicators of research progress) The project milestones are organized as laboratory work (mostly done in-house by project staff) and field work (often done in collaboration with other scientists). They are further subdivided with respect to insect species/groups. The project plan has considerable inherent flexibility. The activities for any one year depend to a great extent on the progress from the previous year, the availability of particular insect species during a given year, satisfactory coordination with field collaborators, reassessment of project priorities, and other factors. Objective 1 - Laboratory research: Year 2005-2006 (FY 06) - 1.1 Attractant studies and development of laboratory bioassay for Diorhabda elongata. Year 2005-2008 (FY 08) - 1.2 Attractant studies and pheromone synthesis for Galerucella spp. Year 2005-2010 (FY 10) - 1.3 Attractant studies on flea beetle species. Year 2005-2006 (FY 06) - 1.4 Complete development of synthesis of Carpophilus spp. pheromones. Objective 2 - Field research: Year 2005-2006 (FY 06) - 2.1 Development of field trapping system for Diorhabda elongata. Year 2005-2009 (FY 09) - 2.2 Trap monitoring system for Galerucella spp. Year 2005-2010 (FY 10) - 2.3 Trapping system for flea beetle species. 4a.List the single most significant research accomplishment during FY 2006. An improved synthetic method for nitidulid beetle pheromones was completed (NP304 Crop Protection and Quarantine, Component 5 - Pest Control Technologies): Nitidulid beetles remain significant pests of a variety of ripe/harvested fruits and grains worldwide. The pheromones (previously discovered at NCAUR) have been commercialized, but the original synthesis has been rather complicated and costly. The new method, using dimethylhydrazone phosphonates as key intermediates, has a smaller number of steps, improved yields, and better product purities than the original method. The new method is expected to lower pheromone cost and lead to better availability of the compounds. 4b.List other significant research accomplishment(s), if any. The host-plant related volatiles were intensively studied for two chrysomelid beetle species, Diorhabda elongata and Galerucella calmariensis (NP304 Crop Protection and Quarantine, Component 2 - Biology of Pests and Natural Enemies): It is now clear that effective synthetic lures for attracting various chrysomelid beetle species must include key compounds from the host plant as well as pheromones. Electrophysiology (the "electroantennogram" technique) was the method used to recognize the important chemicals in the complex plant-volatile mixtures. Use of lures including both pheromones and host volatiles will provide land managers the most potent detection/population-manipulation tools for these important biological control agents. 4c.List significant activities that support special target populations. None. 4d.Progress report. Our group made a concerted effort to begin studying attractants (in particular, a pheromone) for the emerald ash borer, Agrilus planipennis. The effort included making arrangements with the Animal and Plant Health Inspection Service-Plant Protection and Quarantine (APHIS-PPQ) scientists in Michigan to obtain live beetles during their annual flight season. So far, the APHIS-PPQ permits branch has denied us permission to work on the species in Peoria, but efforts continue to obtain permit. The range of the species has spread considerably in the U.S. during FY 2006, including into Illinois, and there remains a clear need for better monitoring/detection tools for this pest. 5.Describe the major accomplishments to date and their predicted or actual impact. Research on pheromones and other semiochemicals is supported under National Program 304. Specifically, this project is relevant to Component II (biology of pests and natural enemies), Component IV (pest exclusion and quarantine), Component V (pest control technologies), Component VI (integrated pest management), and Component IX (basic biology of biocontrol agents). A major part of the project deals with the pheromones of beetles in the family Chrysomelidae. This is a large and economically important family but is still rather poorly known with respect to pheromone chemistry and biology. The family contains serious crop pests, but it also contains important biological control agents for invasive weeds. In both cases, synthetic pheromones could become valuable tools for monitoring or manipulating the insects in ways that are advantageous to agriculture. Furthermore, the project is generating new basic information about the chemistry and biological function of the pheromones in this beetle family. During this project period, the male-produced aggregation pheromone of Galerucella calmariensis has been structurally identified, synthesized, and shown to be attractive in the field, and the further progress has been made on the pheromone and host-derived attractants for Diorhabda elongata. These beetle species are effective biological control agents for purple loosestrife and saltcedar, respectively, and the research is developing a scientific underpinning for future practical tools for the biocontrol program. Significant progress has also been made on a pest species, the eggplant flea beetle Epitrix fuscula. This species has had a devastating impact to organic farmers in the Peoria area, and the pheromone has potential in non-insecticidal pest management. An improved synthetic method has been developed for a series of pheromone components for nitidulid beetles of the genus, Carpophilus. 6.What science and/or technologies have been transferred and to whom? When is the science and/or technology likely to become available to the end-user (industry, farmer, other scientists)? What are the constraints, if known, to the adoption and durability of the technology products? The new synthetic method for the nitidulid beetle pheromones has been communicated to a current producer in the U.S. We continue to work with scientists and land managers regarding the effectiveness and practical use of attractant lures for biocontrol agents, including Diorhabda elongata and Galerucella spp. The technology is of definite interest to land managers and scientists, and it is gaining acceptance incrementally as improvements are made and practical experience is acquired. Other scientists, such as from the Hungarian Academy of Science, Budapest, Hungary, are using attractants developed for the Phyllotreta flea beetles and expanding this area of research to species in Europe. 7.List your most important publications in the popular press and presentations to organizations and articles written about your work. (NOTE: List your peer reviewed publications below). J. Grossman, Conference Notes: ESA 2005 Annual Meeting Highlights (section on NCAUR Flea Beetle Aggregation Pheromone Research), The IPM Practitioner (Bio-Integral Resource Center, Berkeley, CA), Volume 28, (Number 1 & 2, January/February), page 13, 2006. R. J. Bartelt, "Male-produced aggregation pheromone in Galerucella beetles," Illinois Natural History Reports, Spring, 2006. Review Publications Petroski, R.J., Bartelt, R.J. 2006. Preparation of Carpophilus lugubris (Coleoptera: Nitidulidae) aggregation pheromone by direct aldehyde homologation [abstract]. First European Chemistry Congress. Paper No. N-PO-130, p. 337. Bartelt, R.J., Cosse, A.A., Zilkowski, B.W., Weisleder, D., Grode, S.H., Wiedenmann, R.N., Post, S.L. 2006. Dimethylfuran-lactone pheromone from males of Galerucella calmariensis and Galerucella pusilla (Coleoptera: Chrysomelidae). Journal of Chemical Ecology 32(3):693-712. Petroski, R.J., Bartelt, R.J. 2006. New phosphonate reagents for aldehyde homologation [abstract]. American Chemical Society National Meeting. Paper No. 539. Cosse, A.A., Bartelt, R.J., Zilkowski, B.W., Bean, D. 2005. Pheromone components and general green leaf attractants for Diorhabda sp. (Coleoptera: Chrysomelidae): Stimuli quantitation and electrophysiological dose-response study [abstract]. National Entomological Society of America Annual Meeting. Paper No. 364. Bosma, W.B., Bartelt, R.J., Momany, F.A. 2006. Determination of the preferred conformation of the bicyclic Galerucella pheromone using density functional theory optimization and calculations of chemical shifts. Journal of Organic Chemistry. 71(13):4748-4758. Zilkowski, B.W., Cosse, A.A., Bartelt, R.J. 2005. Identification and attractiveness of (2E,4E,6Z)-2,4,6-nonatrienal, the major component of the male-produced aggregation pheromone of the eggplant flea beetle (Epitrix fuscula) [abstract]. Entomological Society of America Annual Meeting. Paper No. 0074. Panizzi, A.R., Berhow, M.A., Bartelt, R.J. 2004. Oviposition of the southern green stink bug, Nezara viridula (L.) on artificial substrates conditioned by chemical extracts from soybean plants [abstract]. XX Brazilian Congress of Entomology, Program and Abstracts. p. 104. Toth, M., Csonka, E., Bartelt, R.J., Cosse, A.A., Zilkowski, B.W., Muto, S., Mori, K. 2005. Pheromonal activity of compounds identified from male Phyllotreta cruciferae: Field tests of racemic mixtures, pure enantiomers, and combinations with allyl isothiocyanate. Journal of Chemical Ecology. 31(11):2705-2720. Bartelt, R.J., Cosse, A.A., Zilkowski, B.W., Weisleder, D., Grode, S.H., Wiedenmann, R.N., Post, S.L. 2005. Male-produced aggregation pheromone of Galerucella calmariensis and G. pusilla [abstract]. National Entomological Society of America Proceedings. Paper No. D0363. Petroski, R.J. 2004. Preparation and deprotection of aldehyde dimethylhydrazones [abstract]. American Chemical Society. Division of Agricultural and Food Chemistry. Paper No. 84. Petroski, R.J., Cosse, A.A., Bartelt, R.J., Zilkowski, B.W. 2005. Practical syntheses of selected insect pheromones. In: Petroski, R.J., Tellez, M.R., Behle, R.W., editors. Semiochemicals in Pest and Weed Control. American Chemical Society, Washington, DC. p. 29-43. Csonka, E., Bartelt, R.J., Cosse, A.A., Zilkowski, B.W., Ujvary, I., Toth, M. 2006. Similarities and differences in pheromonal and host-plant related chemical communication of flea beetles Phyllotreta cruciferae Goeze and Phyllotreta vittula Redtenbacher (Coleoptera, Chrysomelidae) [abstract]. International Society of Chemical Ecology Meeting. Poster No. S5-P28, p. 211. Petroski, R.J. 2006. Preparation and deprotection of aldehyde dimethylhydrazones. Synthetic Communications. 36(12):1727-1734. Petroski, R.J. 2004. Deprotection of aldehyde dimethylhydrazones with glyoxylic acid. American Chemical Society Abstracts. Paper No. 397; p. 184.