Monofluoro Analogs of Eugenol Methyl Ether as Novel Attractants for the Oriental Fruit Fly

Di- and Tri-fluorinated Analogs of Methyl Eugenol: Attraction to and Metabolism in the Oriental Fruit Fly, Bactrocera Dorsalis (Hendel)

“…In any case, a moderate (II) or poor (I) ability to attract flies in the field, and likely higher costs of syntheses, make trifluoroanalog I and difluoroanalog II unlikely replacements for ME as attractants for the Oriental fruit fly. Our field tests, however, showed good catches in traps baited with FME, confirming our earlier findings (Khrimian et al, 1994(Khrimian et al, , 2006(Khrimian et al, , 2009Liquido et al, 1998) that this compound is equally attractive to B. dorsalis and also a longer-lived lure.…”

“…In field tests, FME was as attractive to B. dorsalis males as ME (Khrimian et al, 1994), while RFME was ∼50% less attractive than ME (Khrimian et al, 2009). In tests, the release rates of RFME and ME were not different (Khrimian et al, 2009), whereas FME was more persistent than ME and, remarkably, about twice as active behaviorally as the corresponding Z isomer (Khrimian et al, 1994;Liquido et al, 1998). In laboratory experiments, both FME and RFME attracted, and were readily consumed by, B. dorsalis males at rates similar to that of ME (Khrimian et al, 2006(Khrimian et al, , 2009.…”

“…Metabolic activation of ME and production of 1′-hydroxy metabolites through enzymatic side-chain hydroxylation are thought to be primarily responsible for hepatotoxicity and carcinogenicity of this compound (Smith et al, 2002). The search for safer alternative attractants has led to the evaluation of a number of phenylpropanoids with structural similarities to ME (Metcalf et al, 1975;Mitchell et al, 1985;Khrimian et al, 1993Khrimian et al, , 1994Khrimian et al, , 2006Khrimian et al, , 2009Liquido et al, 1998).…”

Stereoselective synthesis of insect sex pheromone analogs having a fluorine atom on their double bonds

“…However, only a few analogs having a fluorine atom on their double bond have been reported [4][5][6].…”

Regiospecific synthesis of symmetrical (1E,3E) 2,3-difluoro-1,4-diphenyl-buta-1,3-dienes via palladium-catalyzed cross-coupling of (Z) 2-bromo-2-fluoroethenylbenzenes in presence of bis(pinacolato)diboron

“…For instance, several analogues of insect pheromones bearing [5,6] fluorine atom in vinylic positions have been synthesized and reported to be more potent attractors than their non-fluorinated counterpart. Analogues of retinal, bearing a fluorine atom in vinylic position are important tools for the study of the process of vision [7,8].…”