Synthesis and repellent efficacy of a new chiral piperidine analog: comparison with Deet and Bayrepel activity in human-volunteer laboratory assays against Aedes aegypti and Anopheles stephensi.
Optically active (1S,2'S)-2-methylpiperidinyl-3-cyclohexen-1-carboxamide (SS220) is a new synthetic arthropod repellent. A three-step synthesis based on a chiral Diels-Alder reaction and diastereomeric resolution of 2-methylpiperidine was developed to prepare the compound. Quantitative laboratory assays using human volunteers compared the effectiveness of SS220 with the commonly used repellents Deet and Bayrepel against Aedes aegypti (Linnaeus) and Anopheles stephensi Liston mosquitoes. In two experiments using Aedes aegypti, one using a single identical dose and one with varying doses used to develop a dose-response curve, SS220 was as effective as Deet and both compounds were more effective than Bayrepel. The three compounds were equally effective against An. stephensi. Based on the ease of its synthetic preparation and its repellent efficacy, we surmise that SS220 is a candidate to serve as a new and effective alternate repellent for protection against arthropod disease vectors.
Klun
Jerome A
JA
USDA-ARS, PSI, Chemicals Affecting Insect Behavior Laboratory, Beltsville, MD 20705, USA.
Khrimian
Ashot
A
Margaryan
Armenak
A
Kramer
Matthew
M
Debboun
Mustapha
M
D000330:Aedes / Q000187:drug effects / Q000502:physiology*; D000818:Animals; D000852:Anopheles / Q000187:drug effects / Q000502:physiology*; D003671:DEET / Q000633:toxicity*; D004305:Dose-Response Relationship, Drug; D006805:Human Experimentation; D006801:Humans; D007302:Insect Repellents / Q000494:pharmacology*; D010880:Piperidines / Q000633:toxicity*; D013237:Stereoisomerism
D007302:Insect Repellents; D010880:Piperidines; D003671:DEET; C483506:picaridin