title: Dihydronepetalactones deter feeding activity by mosquitoes, stable flies, and deer ticks.
abstract: The essential oil of catmint, Nepeta cataria L., contains nepetalactones, that, on hydrogenation, yield the corresponding dihydronepetalactone (DHN) diastereomers. The DHN diastereomer (4R,4aR,7S,7aS)-4,7-dimethylhexahydrocyclopenta[c]pyran-1(3H)-one, DHN 1) was evaluated as mosquito repellent, as was the mixture of diastereomers {mostly (4S,4aR,7S,7aR)-4,7-dimethylhexahydrocyclopenta[c]pyran-1(3H)-one, DHN 2} present after hydrogenation of catmint oil itself. The repellency of these materials to Aedes aegypti L. and Anopheles albimanus Wiedemann mosquitoes was tested in vitro and found to be comparable to that obtained with the well-known insect repellent active ingredient N,N-diethyl-3-methylbenzamide (DEET). DHN 1 and DHN 2 also repelled the stable fly, Stomoxys calcitrans L., in this study. DHN 1, DHN 2, and p-menthane-3,8-diol (PMD), another natural monoterpenoid repellent, gave comparable levels of repellency against An. albimanus and S. calcitrans. Laboratory testing of DHN 1 and DHN 2 using human subjects with An. albimanus mosquitoes was carried out. Both DHN 1 and DHN 2 at 10% (wt:vol) conferred complete protection from bites for significant periods of time (3.5 and 5 h, respectively), with DHN2 conferring protection statistically equivalent to DEET. The DHN 1 and DHN 2 diastereomers were also efficaceous against black-legged tick (Ixodes scapularis Say) nymphs.
authors: Central Research & Development, E. I. DuPont de Nemours and Company, Wilmington, DE 19880-0328, USA.
authors: John E
authors: JE
authors: Feaster
authors: Mark A
authors: MA
authors: Scialdone
authors: Robin G
authors: RG
authors: Todd
authors: Yamaira I
authors: YI
authors: Gonzalez
authors: Joseph P
authors: JP
authors: Foster
authors: David L
authors: DL
authors: Hallahan
mesh_terms: D000330:Aedes / Q000187:drug effects* / Q000502:physiology; D000818:Animals; D000852:Anopheles / Q000187:drug effects* / Q000502:physiology; D000081004:Cyclopentane Monoterpenes; D003517:Cyclopentanes / Q000494:pharmacology*; D005247:Feeding Behavior / Q000187:drug effects; D006801:Humans; D007299:Insect Bites and Stings / Q000517:prevention & control; D007300:Insect Control / Q000379:methods*; D007302:Insect Repellents / Q000494:pharmacology*; D018884:Ixodes / Q000187:drug effects* / Q000502:physiology; D009117:Muscidae / Q000187:drug effects* / Q000502:physiology; D011753:Pyrones / Q000494:pharmacology*
chemical_list: D000081004:Cyclopentane Monoterpenes; D003517:Cyclopentanes; D007302:Insect Repellents; D011753:Pyrones; C543438:dihydronepetalactone; C115644:nepetalactone