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ARS Home » Pacific West Area » Albany, California » Western Regional Research Center » Bioproducts Research » Research » Publications at this Location » Publication #365093

Research Project: Bioproducts from Agricultural Feedstocks

Location: Bioproducts Research

Title: Ketalization of 2-Heptanone to prolong its activity as mite repellant for the protection of honey bees

Author
item BORRIES, FREDERIC - Rochester Institute Of Technology
item KUDLA, AMBER - Rochester Institute Of Technology
item KIM, SEOHYUN - Rochester Institute Of Technology
item ALLSTON, THOMAS - Rochester Institute Of Technology
item EDDINGSAAS, NATHAN - Rochester Institute Of Technology
item Shey, Justin
item Orts, William - Bill
item Klamczynski, Artur
item Glenn, Gregory - Greg
item MIRI, MASSOUD - Rochester Institute Of Technology

Submitted to: Journal of the Science of Food and Agriculture
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 6/13/2019
Publication Date: 7/1/2019
Citation: Borries, F.A., Kudla, A.M., Kim, S., Allston, T.D., Eddingsaas, N.C., Shey, J., Orts, W.J., Klamczynski, A.P., Glenn, G.M., Miri, M.J. 2019. Ketalization of 2-Heptanone to prolong its activity as mite repellant for the protection of honey bees. 99(14):6267-6277. Journal of the Science of Food and Agriculture. https://doi.org/10.1002/jsfa.9900.
DOI: https://doi.org/10.1002/jsfa.9900

Interpretive Summary: 2-Heptanone is a natural chemical produced by honeybees that can repel parasitic mites but it is difficult to release slowly over time due to its volatility. Scientists at the Rochester Institute of Technology in collaboration with USDA-ARS scientists in Albany, CA successfully synthesized a chemical derivative of 2-heptanone that was non-volatile and degraded slowly into 2-heptanone over time resulting in a slow-release system. This research could help in the development of a safe, pesticide-free control system for parasitic mites in honeybees.

Technical Abstract: 2-Heptanone is a volatile liquid known to be effective in protecting honey bees from parasitic mite infestations in hives. The goal of this investigation was to show that chemical derivatives of 2-heptanone would release the ketone for a significantly longer time than it takes for the pure ketone to evaporate and preferably for as long as two brood cycles of a honey bee (42 days). A liquid ketal of 2-heptanone with glycerol (Glyc-Ket) and solid ketals of the ketone with polyvinyl alcohol (PVAl-Ket), containing different amounts of the ketone, were synthesized. The fully resolved 1H and 13C NMR spectra of the ketals are discussed. In case of the polymer, also Differential Scanning Calorimetry (DSC) of a ketal has been compared to the unketalized polyvinyl alcohol. The length of time by which 2-heptanone was released by the ketals was determined by GC-MS of the headspace. In case of Glyc-Ket, also the concentration of the 2-heptanone in the liquid phase was monitored by 1H NMR spectroscopy. The deketalization was pH dependent, ranging for the Glyc-Ket between 2.0 and 2.5 and for the PVAl-Ket between 2.0 and 3.5.