Repellent activities of stereoisomers of p-menthane-3,8-diols against Anopheles gambiae (Diptera: Culicidae).
Four stereoisomers of p-menthane-3,8-diol, which make up the natural product obtained from Eucalyptus citriodora, were synthesized through stereoselective procedures. Repellency assays showed that all the four were equally active against Anopheles gambiae s.s. Racemic blends and the diastereoisomeric mixture of all the four isomers were also equally repellent. 1-alpha-terpeneol, with a single hydroxyl function at C-8 and unsaturation at C-8, and menthol, with a single hydroxyl function at C-3, were not repellent. The practical implication of these results is discussed.
D000818:Animals; D000852:Anopheles / Q000187:drug effects* / Q000502:physiology; D000081005:Cyclohexane Monoterpenes; D005052:Eucalyptus / Q000737:chemistry; D005260:Female; D007302:Insect Repellents / Q000737:chemistry / Q000494:pharmacology*; D008610:Menthol / Q000031:analogs & derivatives / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D009032:Mosquito Control / Q000379:methods*; D018515:Plant Leaves / Q000737:chemistry; D013237:Stereoisomerism
D000081005:Cyclohexane Monoterpenes; D007302:Insect Repellents; D008610:Menthol; C005804:terpin