Predicting mosquito repellent potency of N,N-diethyl-m-toluamide (DEET) analogs from molecular electronic properties.

Abstract

Specific molecular electronic properties of 30 N,N-diethyl-m-toluamide (DEET) analogs demonstrate functional dependence with their reported duration of protection against mosquito bites, thus providing predictors of insect repellent efficacy. No single electronic property is sufficient to predict repellent efficacy as measured by protection time, rather a set of specific electronic properties is required. Thus, the values of the van der Waals surface electrostatic potential by the amide nitrogen and oxygen atoms, the atomic charge at the amide nitrogen atom, and the dipole moment must all be in optimal ranges for potent repellency. The electronic properties were calculated using the AM1 semi-empirical quantum chemical method using commercial software. These easily calculable predictors of repellent efficacy should be useful in predicting the relative efficacy of newly designed compounds, thus guiding the selection of new repellents for testing.

Prevention of arthropod-related disease

“…Although field trials remain the gold standard for evaluation of any new repellent, arm box studies and in vitro predictive values such as the van der Waals surface electrostatic potential, the atomic charge at the amide nitrogen atom, and the dipole moment are useful to identify new agents for field testing. 38 One-piperidinecarboxylic acid, 2-(2-hydroxyethyl)-, 1-methylpropylester (KBR 3023, Picaridin, Bayrepel½Bayer AG, Leverkusen, and Autan ½SC Johnson) was as effective as deet in field trials against a variety of mosquitoes in Queensland, Australia, 39 and Africa. 40 Preventing disease from ticks and mites…”

Essential oils and their components as an alternative in the control of mosquito vectors of disease

“…El momento dipolar es un indicador de la lipofilia y la hidrofobia (128) y se lo ha asociado con la actividad repelente (129). Por otra parte, se ha demostrado que los repelentes más eficaces poseen un punto de ebullición y una presión de vapor que les permite tener mayor tiempo de contacto con los mosquitos (127).…”

Behavioral Responses and Bioefficacy of Some Aromatic Amides Against Aedes aegypti

“…However, the adverse effects related to the use of DEET, such as its skin irritancy, disagreeable cosmetic effects, penetration through skin, central nervous system disturbances in prolonged use, and other adverse reactions in children and adult. In addition, DEET is a plasticizer that reacts with certain plastics and synthetic rubber (Windheuser et al 1982, Ma et al 1999, Wang et al 2006, Innocent et al 2008. The alternative dimethylphthalate also had to be replaced in India because of its low efÞcacy .…”