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Ring-Fluorinated Analog of Methyl Eugenol: Attractiveness to and Metabolism in the Oriental Fruit Fly, Bactrocera Dorsalis (Hendel)

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Abstract

Oriental fruit fly, Bactrocera dorsalis (Hendel), males are highly attracted to the natural phenylpropanoid methyl eugenol (ME). They compulsively feed on ME and metabolize it to ring and side-chain hydroxylated compounds that have both pheromonal and allomonal functions. Side-chain metabolic activation of ME leading to (E)-coniferyl alcohol has long been recognized as a primary reason for hepatocarcinogenicity of this compound in rodents. Earlier, we demonstrated that introduction of a fluorine atom at the terminal carbon of the ME side chain significantly depressed metabolism and specifically reduced formation of coniferyl alcohol but had little effect on field attractiveness to B. dorsalis. In the current paper, we demonstrate that fluorination of ME at the 4 position of the aromatic ring blocks metabolic ring-hydroxylation but overall enhances side-chain metabolism by increasing production of fluorinated (E)-coniferyl alcohol. In laboratory experiments, oriental fruit fly males were attracted to and readily consumed 1,2-dimethoxy-4-fluoro-5-(2-propenyl)benzene (I) at rates similar to ME but metabolized it faster. Flies that consumed the fluorine analog were as healthy post feeding as ones fed on methyl eugenol. In field trials, the fluorine analog I was ∼50% less attractive to male B. dorsalis than ME.

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Notes

  1. Mention of commercial products does not constitute an endorsement by USDA.

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Acknowledgments

We thank Peter Bianchi, Taina Burke, Sarah Marshall, Rachel Morton, Charmaine Sylva, and Judy Yoshimoto for technical assistance with the field bioassays.

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Authors and Affiliations

  1. Invasive Insect Biocontrol and Behavior Laboratory, Beltsville Agricultural Research Center, USDA-ARS, Bldg. 007, Rm. 301, 10300 Baltimore Avenue, Beltsville, MD, 20705, USA

    Ashot Khrimian & Filadelfo Guzman

  2. Eastern Mennonite University, 1200 Park Road, Harrisonburg, VA, 22802, USA

    Matthew S. Siderhurst

  3. Pacific Basin Agricultural Research Center, Pacific West Area, USDA-ARS, 64 Nowelo St, Hilo, HI, 96720, USA

    Grant T. Mcquate, Janice Nagata, Lori Carvalho & Eric B. Jang

  4. Plant Epidemiology and Risk Analysis Laboratory, USDA-APHIS-PPQ, Center for Plant Health Science and Technology, Prince Kuhio Federal Building, Room 8-109, 300 Ala Moana Blvd, Honolulu, HI, 96850, USA

    Nicanor J. Liquido

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  1. Ashot Khrimian
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  2. Matthew S. Siderhurst
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  3. Grant T. Mcquate
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  4. Nicanor J. Liquido
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  5. Janice Nagata
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Correspondence to Ashot Khrimian.

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Khrimian, A., Siderhurst, M.S., Mcquate, G.T. et al. Ring-Fluorinated Analog of Methyl Eugenol: Attractiveness to and Metabolism in the Oriental Fruit Fly, Bactrocera Dorsalis (Hendel). J Chem Ecol 35, 209–218 (2009). https://doi.org/10.1007/s10886-008-9581-5

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  • DOI: https://doi.org/10.1007/s10886-008-9581-5

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