Structure–activity relationships of larvicidal monoterpenes and derivatives against Aedes aegypti Linn

• Published in: Chemosphere (Oxford) 2011-06, Vol.84 (1), p.150-153
• Main Authors: Santos, Sandra R.L., Melo, Manuela A., Cardoso, Andrea Valença, Santos, Roseli L.C., de Sousa, Damião P., Cavalcanti, Sócrates C.H.
• Format: Article
• Language: English
• Subjects: Aedes - drug effects; Aedes aegypti; Animals; Biological and medical sciences; Chemosphere; Collection; Cyclohexenes - toxicity; Derivatives; Empirical analysis; Essential oil; Fundamental and applied biological sciences. Psychology; Hydrocarbons; Insecticides - chemistry; Insecticides - toxicity; Larva - drug effects; Larvicidal activity; Limonene; Lipophilicity; Medically important nuisances and vectors, pests of stored products and materials: population survey and control; Monoterpene; Monoterpenes - chemistry; Monoterpenes - toxicity; Polarity; Searching; Structure-Activity Relationship; Structure–activity relationships; Terpenes - toxicity; Vectors. Intermediate hosts
• ISSN: 0045-6535; 1879-1298
• DOI: 10.1016/j.chemosphere.2011.02.018

► Structure−activity of monoterpenes against Ae. aegypti larvae. ► Heteroatoms in the monoterpene structure decreases potency. ► Conjugated and exo double bonds appear to increase larvicidal potency. ► Hydroxyls in the cyclic structure resulted in decreased potency. ► Limonene exhibited the highest larvicidal activity. In the search for larvicidal compounds against Aedes aegypti L. (Diptera: Culicidae), a collection of monoterpenes were selected and evaluated. R- and S-limonene exhibited the highest larvicidal potency (LC50=27 and 30ppm, respectively), followed by γ-terpinene (LC50=56ppm) and RS-carvone (LC50=118ppm). Structural characteristics which may contribute to the understanding of the larvicidal activity of monoterpenes were empirically identified. The presence of heteroatoms in the basic hydrocarbon structure decreases larvicidal potency. Conjugated and exo double bonds appear to increase larvicidal potency. Replacement of double bonds by more reactive epoxides decreases the larvicidal potency. The presence of hydroxyls in the cyclic structure resulted in decreased potency, probably due to increased polarity indicanting that lipophilicity seems to play an important role in increasing the larvicidal potency in this set of compounds.