Repellency of some phenylphenols and related compounds to house flies.
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Seven novel oxazolidines from 5-methyl-4-hexenal were synthesized, characterized, and evaluated in a cloth test system as mosquito repellents. These heterocycles were a homologous series of 3-alkanoyl-2-(4'-methyl-3'-pentenyl)oxazolidines, with substituents at N-3 ranging from acetyl to n-nonanoyl groups. Carbon-13 NMR spectroscopy at 100.6 MHz revealed that these molecules existed in deuterochloroform solution as unequal mixtures of cis (syn)- and trans (anti)-rotational isomers. At 25 degrees C, this isomerism at the amide group resulted in two detectable 13C signals for all assigned carbon atoms, except for the methyl carbons of the isopentenyl side chain. Differences in 13C chemical shifts for the methyl group at N-3 were observed up to the n-butanoyl homologue. The 13C signal assignments were aided by the distortionless enhancement by polarization transfer (DEPT) spectral editing technique. Two-dimensional carbon-hydrogen chemical shift correlation experiments aided in partially interpreting the complex proton spectra of these molecules. Repellent activity of the acetyl, trideuteroacetyl, and propionyl derivatives was observed in bioassays with three mosquito species, but the long-chain homologues were practically ineffective as mosquito repellents.
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Essential oils of six plants growing in Kenya were screened for repellent activities against Anopheles gambiae sensu stricto. The oils of Conyza newii (Compositeae) and Plectranthus marrubioides (Labiateae) were the most repellent (RD50=8.9 x 10(-5) mg cm(-2), 95% CI) followed by Lippia javanica (Verbenaceae), Lippia ukambensis (Verbenaceae), Tetradenia riparia, (Iboza multiflora) (Labiateae) and Tarchonanthus camphoratus (Compositeae). Eight constituents of the different oils (perillyl alcohol, cis-verbenol, cis-carveol, geraniol, citronellal, perillaldehyde, caryophyllene oxide and a sesquiterpene alcohol) exhibited relatively high repellency. Four synthetic blends of the major components (present in > or = 1.5%) of the essential oils were found to exhibit comparable repellent activity to the parent oils.
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A plant-derived mosquito repellent, based on the oil of Eucalyptus maculata var. citriodora Hook, was evaluated against the biting midge Culicoides imicola Kieffer. Suction black light-traps covered with repellent-impregnated polyester mesh and deployed near horses attracted large numbers of C. imicola, which were seen near the treated net within a few minutes of the start of the experiment. Initial collections in the traps were approximately 3 times as large as those in control traps with untreated mesh. Numbers collected in treated traps were similar to untreated control traps after 4 h. Traps with mesh treated with DEET or another plant-derived (Meliaceae) proprietary product, AG1000, acted as repellents relative to the control. The differential activity of repellents against blood-feeding Diptera is discussed.
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