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United States Department of Agriculture

Agricultural Research Service

Research Project: BITING ARTHROPODS: INTEGRATED PEST MANAGEMENT

Location: Mosquito and Fly Research Unit

Title: Structure-activity relationship in 34 trifluoromethylphenyl amides against Aedes aegypti

Authors
item Tsikolia, Maia
item Bernier, Ulrich
item Agramonte, Natasha
item Coy, Monique
item Alden, Estep -
item Becnel, James
item Clark, Gary
item Linthicum, Kenneth

Submitted to: Meeting Abstract
Publication Type: Abstract Only
Publication Acceptance Date: August 14, 2014
Publication Date: N/A

Technical Abstract: As part of our mission to discover new mosquito insecticides, 34 trifluoromethylphenyl amides were designed and synthesized. These compounds have trifluoromethyl- groups located in the ortho-, meta- or para- positions on the phenyl ring and have various substituents attached to the carbonyl carbon, e.g. 2,6-dinitrophenyl, 2-methylphenyl, trifluoromethyl, pentafluoroethyl, 2-chloroethyl, 3-pentyl or n-alkyl (pentyl, hexyl, heptyl, nonyl and decyl) groups. These compounds were evaluated for toxicity against Ae. aegypti larvae and adult female and for repellency against adult female Ae. aegypti. The most active compounds were those that had either halogenated moiety in the ortho- position to the amide group, or those with halogenated moiety attached to the carbonyl carbon. The presence of a 2,6-dichloro group increased larvicidal and repellent activity of para- substituted trifluoromethylphenyl amides when the trifluoromethyl- or aromatic group (2,6-dinitrophenyl or 2-methylphenyl) was attached to the carbonyl carbon. Larvicidal and repellent activity decreased when an alkyl group such as 3-pentyl or n-pentyl was attached to the carbonyl carbon. In ortho- and meta- trifluoromethyl, and, also, 2,6-dichloro- para- trifluoromethyl amides, the repellent activity increased when either trifluoromethyl or pentafluoroethyl group was attached to the amide carbon. Repellency decreased when the n-alkyl group (hexyl, heptyl, nonyl or decyl) or aromatic group (2,6-dinitrophenyl or 2-methylphenyl) was attached to the amide carbon. These structure-activity trends are being used for the design of novel mosquito insecticides and repellents. We are currently designing, synthesizing and bioassayng a new generation of compounds. Data generated from these new compounds will be used to produce a quantitative structure–activity relationship model (QSAR) for these compounds.

Last Modified: 12/19/2014
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