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Consumption and Metabolism of 1,2-Dimethoxy-4-(3-Fluoro-2-Propenyl)Benzene, a Fluorine Analog of Methyl Eugenol, in the Oriental Fruit Fly Bactrocera dorsalis (Hendel)

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Abstract

Methyl eugenol (ME) is a natural phenylpropanoid highly attractive to oriental fruit fly Bactrocera dorsalis (Hendel) males. The flies eagerly feed on ME and produce hydroxylated metabolites with both pheromonal and allomonal functions. Side-chain metabolic activation of ME has long been recognized as a primary reason for hepatocarcinogenicity of this compound on rodents. In an attempt to develop a safer alternative to ME for fruit fly management, we developed a fluorine analog 1,2-dimethoxy-4-(3-fluoro-2-propenyl)benzene (I), which, in earlier field tests, was as active to the oriental fruit fly as ME. Now we report that B. dorsalis males are not only attracted to, but also eagerly consume (up to ∼1 mg/insect) compound I, thus recognizing this fluorinated benzene as a close kin of the natural ME. The flies metabolized the fluorine analog I in a similar fashion producing mostly two hydroxylated products, 2-(3-fluoro-2-propenyl)-4,5-dimethoxyphenol (II) and (E)-coniferyl alcohol (III), which they stored in rectal glands. However, the introduction of the fluorine atom at the terminal carbon atom of the double bond favors the ring hydroxylation over a side-chain metabolic oxidation pathway, by which coniferyl alcohol is produced. It also appears that fluorination overall impedes the metabolism: at high feed rate (10 μl per 10 males), the flies consumed in total more fluorine analog I than ME but were unable to metabolize it as efficiently as ME.

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Acknowledgments

The authors thank Nikki Dees and Filadelfo Guzman for assistance in syntheses and analyses.

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Authors and Affiliations

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

    Ashot Khrimian

  2. Pacific Basin Agricultural Research Center, Pacific West Area, USDA-ARS, 920 Stainback Highway, Hilo, HI, 96720, USA

    Eric B. Jang, Janice Nagata & Lori Carvalho

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  1. Ashot Khrimian
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  2. Eric B. Jang
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  3. Janice Nagata
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  4. Lori Carvalho
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Correspondence to Ashot Khrimian.

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Khrimian, A., Jang, E.B., Nagata, J. et al. Consumption and Metabolism of 1,2-Dimethoxy-4-(3-Fluoro-2-Propenyl)Benzene, a Fluorine Analog of Methyl Eugenol, in the Oriental Fruit Fly Bactrocera dorsalis (Hendel). J Chem Ecol 32, 1513–1526 (2006). https://doi.org/10.1007/s10886-006-9066-3

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  • DOI: https://doi.org/10.1007/s10886-006-9066-3

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