Insecticidal and repellent properties of novel trifluoromethylphenyl amides II

This project focused on the design, synthesis, and testing of trifluoromethylphenyl amides (TFMPAs) as potential mosquitocides and repellents. Fourteen compounds were evaluated for toxicity against larvae and adults of Aedes aegypti. Several compounds were toxic against Aedes aegypti (larval, adult and feeding bioassays) and Drosophila melanogaster (glass-surface contact assay), but were much less toxic than fipronil, with toxicity ratios ranging from 100-fold in the larval assay to 100,000-fold for topical application to adult insects. In repellency bioassays to determine minimum effective dosage (MED), compound N-(2,6-dichloro-4(trifluoromethyl)phenyl)-2,2,3,3,3-pentafluoropropanamide (7b) repelled Ae. aegypti females at lower concentration, 0.017 (+/- 0.006) mu mol/cm(2), than N, N-diethyl-meta-toluamide (DEET) 0.026 (+/- 0.005) mu mol/cm(2). 2-Chloro-N-(3-(trifluoromethyl)phenyl)acetamide (6a) performed better than DEET against two species of mosquitoes: it repelled Ae. aegypti females at 0.013 (+/- 0.006) mu mol/cm(2) and Anopheles gambiae females (in a warm body repellent assay), at a standard exposure of 2 nmol/cm(2). These studies revealed novel active structures that could further lead to compounds with better repellent activity.