|CHALAIRE, KATELYN - Department Of Defense|
|Linthicum, Kenneth - Ken|
|COY, MONIQUE - Former ARS Employee|
|SWALE, DANIEL - University Of Florida|
|BLOOMQUIST, JEFFREY - University Of Florida|
Submitted to: Meeting Abstract
Publication Type: Abstract Only
Publication Acceptance Date: 1/22/2013
Publication Date: 2/24/2013
Citation: Tsikolia, M., Bernier, U.R., Agramonte, N.M., Tabanca, N., Wedge, D.E., Chalaire, K.C., Becnel, J.J., Clark, G.G., Linthicum, K., Coy, M.R., Swale, D., Bloomquist, J.R. 2013. Trifluoromethylphenyl amides as novel insecticides and fungicides. Abstract for the American Mosquito Control Association Meeting in Atlantic City, NJ on February 24 - 28, 2013. pgs.30-31.
Technical Abstract: Because of increased resistance to insecticides in arthropods, it is necessary to identify new chemicals that may have novel modes of action. Following an extensive literature search for compounds with insecticidal and mosquito repellent activity, we have designed and synthesized a set of 20 trifluoromethylphenyl amides. These compounds were evaluated for toxicity against Aedes aegypti larvae and adults, for repellency against female Ae. aegypti and Anopheles albimanus, and for fungicidal activity against fungal species. Selected compounds were evaluated for toxicity against Drosophila melanogaster and, unlike fipronil, showed full activity against a resistant strain having an altered gamma-aminobutyric acid (GABA) receptor. The most potent compounds from this initial evaluation were used to design and synthesize 14 additional derivatives. From the bioassays of these amides, 2 compounds, N-(3-(trifluoromethyl)phenyl)acetamide and N-(2,6-dicholaro-4-(trifluoromethyl)phenyl)-2,2,3,3,3-pentafluoropropanamide, repelled Ae. aegypti at lower concentration than DEET. These same 2 compounds and 2-cholor-N-(2,6-dichloro-4-(trifluoromethyl)phenyl) acetamide exhibited comparable fungicidal activity to the standards, azoxystrobin and captan, against Phomopsis viticola and Colletotrichum acutatum fungi. In the future, we plan to conduct a QSPR study using the insecticidal activity of all 34 trifluoromethylphenyl amides as the properties for input into the model.