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Insecticidal and repellent properties of novel trifluoromethylphenyl amides III

Tsikolia, M., Bernier, Ulrich R., Agramonte, Natasha M., Estep, Alden S., Becnel, James J., Linthicum, Kenneth J., Bloomquist, Jeffrey R.
Pesticide biochemistry and physiology 2019
Aedes aegypti, adults, deet, females, fipronil, larvae, larvicides, lethal concentration 50, lethal dose 50, repellents
The adulticidal, larvicidal, and repellent activity of 18 trifluoromethylphenyl amides (TFMPAs) was determined against Aedes aegypti mosquitoes. The compounds studied are the third generation designed from active structures of the previous two generations. N-(3,5-Bis(trifluoromethyl)phenyl)-2-chloroacetamide (8f) and N-(3,5-bis(trifluoromethyl)phenyl)-2,2,3,3,3-pentafluoropropanamide (8h) were most active against 1st stage Ae. aegypti larvae with LC50 values of 125 and 2.53 μM; for comparative purposes, the published LC50 for fipronil is 0.014 μM. Compound 8h was the most toxic against adult female Ae. aegypti with an LD50 = 2.12 nmol/mg, followed by 8f, and N-(3,5-bis(trifluoromethyl)phenyl)-2,2,2-trifluoroacetamide (8g) with LD50 values of 4.27 and 4.73 nmol/mg, respectively, although these compounds were significantly less toxic than fipronil against adult female Ae. aegypti. Compounds N-(2-(trifluoromethyl)phenyl)butyramide (9c), N-(2-(trifluoromethyl)phenyl)pentanamide (9d) and N-(2-(trifluoromethyl)phenyl)hex-5-enamide (9e) were the best repellents for female Ae. aegypti, with minimum effective dosages (MEDs) of 0.026, 0.052, and 0.091 μmol/cm2, respectively, compared to DEET at 0.052 μmol/cm2. Out of 52 TFMPAs (total number of compounds from three generations of this research) compound 9c was the most active repellent along with two synthesized in our previous studies, 2-chloro-N-(3-(trifluoromethyl)phenyl)acetamide (6a) and 2,2,2-trifluoro-N-(2-(trifluoromethyl)phenyl)acetamide (4c).