Journal of Chemical Ecology (2009) 35, 209-218

Ashot Khrimian, Matthew S. Siderhurst, Grant T. McQuate, Nicanor J. Liquido, Janice Nagata, Lori Carvalho, Filadelfo Guzman and Eric B. Jang (2009)
Ring-fluorinated analog of methyl eugenol: Attractiveness to and metabolism in the Oriental fruit fly, Bactrocera dorsalis (Hendel)
Journal of Chemical Ecology 35 (2), 209-218
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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Link to article at publishers website
Database assignments for author(s): Ashot Khrimian, Matthew Samuel Siderhurst, Grant T. McQuate, Eric B. Jang

Research topic(s) for pests/diseases/weeds:
pheromones/attractants/traps

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Pest and/or beneficial records:

Beneficial	Pest/Disease/Weed	Crop/Product	Country	Quarant.
	Bactrocera dorsalis