Accession Number:

ADA529318

Title:

Novel Carboxamides as Potential Mosquito Repellents

Descriptive Note:

Journal article

Corporate Author:

AGRICULTURAL RESEARCH SERVICE GAINESVILLE FL CENTER FOR MEDICAL AGRICULTURAL AND VETERINARY ENTOMOLOGY

Personal Author(s):

• Katritzky, Alan R.
• Wang, Zuoquan
• Slavov, Svetoslav
• Dobchev, Dimitar A.
• Hall, C. D.
• Tsikolia, Maia
• Bernier, Ulrich R.
• Elejalde, Natasha M.
• Clark, Gary G.
• Linthicum, Kenneth J.

Report Date:

2010-09-01

Pagination or Media Count:

16.0

Abstract:

A model was developed using 167 carboxamide derivatives, from the United States Department of Agriculture archival database, that were tested as arthropod repellents over the past 60 yr. An artificial neural network employing CODESSA PRO descriptors was used to construct a quantitative structure-activity relationship model for prediction of novel mosquito repellents. By correlating the structure of these carboxamides with complete protection time, a measure of repellency based on duration, 34 carboxamides were predicted as candidate mosquito repellents. There were four additional compounds selected on the basis of their structural similarity to those predicted. The compounds were synthesized either by reaction of 1-acylbenzotriazoles with secondary amines or by reaction of acid chlorides with secondary amines in the presence of sodium hydride. The biological efficacy was assessed by duration of repellency on cloth at two dosages 25 and 2.5 molcm2 and by the minimum effective dosage to prevent Aedes aegypti L. Diptera Culicidae bites. One compound, E-N-cyclohexyl-N-ethyl-2-hexenamide, was superior to N,N-diethyl-3-methylbenzamide deet at both the high dosage 22 d versus 7 d for deet and low dosage 5 d versus 2.5 d for deet. Only one of the carboxamides, hexahydro-1-1-oxohexyl-1H-azepine, had a minimum effective dosage that was equivalent or slightly better than that of deet 0.033 molcm2 versus 0.047 molcm2.

Descriptors:

• *CULICIDAE
• *PHYSICOCHEMICAL PROPERTIES
• *INSECT REPELLENTS
• MOLECULAR STRUCTURE
• LONG RANGE(TIME)
• TEST METHODS
• QUANTITATIVE ANALYSIS
• TABLES(DATA)

Subject Categories:

• Agricultural Chemistry
• Biology

Distribution Statement:

APPROVED FOR PUBLIC RELEASE