Diethyltoluamide - N,N,Dietiltoluamide - N,N-diethyl-m-toluamid
Rating : 7
Evaluation | N. Experts | Evaluation | N. Experts |
---|---|---|---|
1 | 6 | ||
2 | 7 | ||
3 | 8 | ||
4 | 9 | ||
5 | 10 |
10 pts from CarPas
Sign up to vote this object, vote his reviews and to contribute to Tiiips.Evaluate | Where is this found? |
"Diethyltoluamide studies" about Diethyltoluamide - N,N,Dietiltoluamide - N,N-diethyl-m-toluamid Review Consensus 10 by CarPas (5225 pt) | 2022-Aug-15 17:19 |
Read the full Tiiip | (Send your comment) |
Compendium of the most significant studies with reference to properties, intake, effects.
McMeniman CJ, Corfas RA, Matthews BJ, Ritchie SA, Vosshall LB. Multimodal integration of carbon dioxide and other sensory cues drives mosquito attraction to humans. Cell. 2014 Feb 27;156(5):1060-71. doi: 10.1016/j.cell.2013.12.044.
Abstract. Multiple sensory cues emanating from humans are thought to guide blood-feeding female mosquitoes to a host. To determine the relative contribution of carbon dioxide (CO2) detection to mosquito host-seeking behavior, we mutated the AaegGr3 gene, a subunit of the heteromeric CO2 receptor in Aedes aegypti mosquitoes....
Ditzen M, Pellegrino M, Vosshall LB. Insect odorant receptors are molecular targets of the insect repellent DEET. Science. 2008 Mar 28;319(5871):1838-42. doi: 10.1126/science.1153121.
Abstract. DEET (N,N-diethyl-meta-toluamide) is the world's most widely used topical insect repellent, with broad effectiveness against most insects. Its mechanism of action and molecular target remain unknown. Here, we show that DEET blocks electrophysiological responses of olfactory sensory neurons to attractive odors in Anopheles gambiae and Drosophila melanogaster. DEET inhibits behavioral attraction to food odors in Drosophila, and this inhibition requires the highly conserved olfactory co-receptor OR83b. DEET inhibits odor-evoked currents mediated by the insect odorant receptor complex, comprising a ligand-binding subunit and OR83b. We conclude that DEET masks host odor by inhibiting subsets of heteromeric insect odorant receptors that require the OR83b co-receptor. The identification of candidate molecular targets for the action of DEET may aid in the design of safer and more effective insect repellents.
Spencer TS, Hill JA, Feldmann RJ, Maibach HI. Evaporation of diethyltoluamide from human skin in vivo and in vitro. J Invest Dermatol. 1979 Jun;72(6):317-9. doi: 10.1111/1523-1747.ep12531755.
Abstract. Relative evaporation and penetration of the insect repellent, N,N-diethyl-m-toluamide, has been measured by 3 methods, 2 in vivo and 1 in vitro. The evaporation rate 30 min after application was found to be similar by all 3 methods. At an applied dose of 0.25 microgram/cm2, 9.6% in vivo and 9.7% in vitro evaporated from the skin in the first hour after application. Although the techniques used produced similar results in vivo and in vitro for diethyltoluamide, studies are being conducted to further elucidate kinetics of loss by evaporation.
Bernier UR, Furman KD, Kline DL, Allan SA, Barnard DR. Comparison of contact and spatial repellency of catnip oil and N,N-diethyl-3-methylbenzamide (deet) against mosquitoes. J Med Entomol. 2005 May;42(3):306-11. doi: 10.1603/0022-2585(2005)042[0306:cocasr]2.0.co;2.
Abstract. Nepetalactone, the primary component of catnip oil, was compared with the repellent N,N-diethyl-3-methylbenzamide (deet) for its ability to affect the host-seeking ability of Aedes aegypti (L.). A triple cage olfactometer was used to bioassay each substance and to assess its attraction inhibition (spatial repellent) attributes when combined with the following attractants: carbon dioxide, acetone, a blend of L-lactic acid and acetone, and human odors. Repellent tests were conducted with each substance against female Ae. aegypti, Anopheles albimanus Weidemann, and Anopheles quadrimaculatus Say. Catnip oil and deet were both weakly attractive to Ae. aegypti, catnip oil was the better spatial repellent, whereas deet was a more effective contact repellent in tests with all three species of mosquitoes.
Moreno-Gómez M, Bueno-Marí R, Carr BT, Bowman GR, Faherty GW, Gobbi C, Palm JM, Van Sloun P, Miranda MÁ. Two New Alternatives to the Conventional Arm-in-Cage Test for Assessing Topical Repellents. J Med Entomol. 2021 Jul 16;58(4):1826-1838. doi: 10.1093/jme/tjab050.
Abstract. ... This study's main goal was to assess alternative laboratory methods for evaluating topical mosquito repellents that use mosquito landing rates more representative of those in the field. The study took place at three European testing labs using 30 study participants per test and the mosquito, Aedes albopictus (Skuse, 1894, Diptera: Culicidae). ...
Merel S, Nikiforov AI, Snyder SA. Potential analytical interferences and seasonal variability in diethyltoluamide environmental monitoring programs. Chemosphere. 2015 May;127:238-45. doi: 10.1016/j.chemosphere.2015.02.025.
Abstract. ...the present study investigates potential interferences affecting the detection and quantification of DEET then the geographical and seasonal variations of DEET concentrations. To examine potential analytical interferences, DEET was analyzed in five geographically-diverse wastewater effluents using both gas chromatography and liquid chromatography coupled to mass spectrometric detectors. ...
Roberts JR, Reigart JR. Does anything beat DEET? Pediatr Ann. 2004 Jul;33(7):443-53.
Abstract. In comparison trials, DEET is more effective than any other insect repellent. Despite some reports of serious adverse events, when comparing the thousands of other reports of exposure and millions of past users, DEET has a good safety record. The appropriate and safest concentration to use on children remains unclear, however. Due to potential absorption through the skin, prudence would dictate that the lowest effective concentration for the time period of exposure be used. Because research has shown that solvents with less skin permeation may be used as an alternative to the ethanol used in some commercial DEET preparations, manufacturers could develop products that are less likely to be absorbed. Pediatricians should be familiar with the duration of action of various formulations of DEET and the efficacy (and in some cases lack of efficacy) of other products in order to advise patients on safe but effective methods of insect control.
Pollack RJ, Kiszewski AE, Spielman A. Repelling mosquitoes. N Engl J Med. 2002 Jul 4;347(1):2-3. doi: 10.1056/NEJM200207043470102.
Abstract. ... Consumers face a bewildering array of “repellent” formulations that contain diverse active ingredients and are sold in packages that bear extraordinary claims. What “works”? What is “safe”? How do “natural” products compare with “synthetic” preparations? How can one make an informed decision about what to purchase?...
Sfara V, Zerba EN, Alzogaray RA. Toxicity of pyrethroids and repellency of diethyltoluamide in two deltamethrin-resistant colonies of Triatoma infestans Klug, 1834 (Hemiptera: Reduviidae). Mem Inst Oswaldo Cruz. 2006 Feb;101(1):89-94. doi: 10.1590/s0074-02762006000100017.
Abstract. The aim of the currrent investigation was to evaluate (a) the toxicity of three pyrethroids (deltamethrin, lambda-cyhalothrin, and tetramethrin); (b) the effect of these insecticides on the locomotor activity; and (c) the repellent effect of N,N-diethyl-m-toluamide (DEET) on two deltamethrin-resistant strains of Triatoma infestans from Argentina (El Chorro and La Toma), and one susceptible strain. The resistance ratios (RRs) obtained for the La Toma strain were: > 10,769, 50.7, and > 5.2 for deltamethrin, lambda-cyhalothrin, and tetramethrin respectively. The RRs for the El Chorro strain were: > 10,769, 85.8, and > 5.2 for deltamethrin, lambda-cyhalothrin, and tetramethrin respectively. The hyperactivity usually caused by the three pyrethroids was in both the deltamethrin-resistant strains compared to the susceptible reference strain. No differences were observed in the repellent effect of DEET between the three groups. These results indicate that the deltamethrin-resistant insects have a cross resistance to lambda-cyhalothrin and tetramethrin, and are also resistant to the first symptom of pyrethroid poisoning (hyperactivity). However, the sensorial process related to DEET repellency does not appear to be altered.
Sign up to vote this object, vote his reviews and to contribute to Tiiips.EvaluateClose | (0 comments) |
"Descrizione" about Diethyltoluamide - N,N,Dietiltoluamide - N,N-diethyl-m-toluamid Review Consensus 10 by CarPas (5225 pt) | 2022-Aug-24 11:58 |
Read the full Tiiip | (Send your comment) |
N,N,Diethyltoluamide (DEET) is a chemical compound derived from toluic acid. It was given the acronym DEET in 1957 by the Committee on Insecticide Terminology of the Entomological Society of America for brevity.
It appears as an oily yellowish liquid, stable, hydrolyses slowly in water. Incompatible with strong oxidising agents, strong acids, strong bases. Flammable.
What it is used for and where
Insect repellent. There are currently more than 100 products worldwide that contain a concentration of between 4% and 100% DEET. The EU Biocides Directive 528/2012, considers repellents to be biocidal products.
Medical
The most commonly used insect and tick repellents on the market are DEET (N,N,Diethyltoluamide), IR3535 (Ethyl Butylacetylaminopropionate) a derivative of β-alanine and Icaridin (Picaridin). IR3535 has a lower level of toxicity and is as effective as DEET. Icaridin has the same efficacy as DEET, but has a lower level of toxicity and a longer duration of protection. A natural product, clove essential oil has shown good repellency, but requires relatively high dosages to cause high effects.
Diethyltoluamide was developed by the US Army as a repellent for the mosquito vector of yellow fever (Aedes aegypti), malaria (Anopheles gambiae), dengue (Aedes aegypti) and chikungunya (Aedes aegypti, Aedes albopictus), in 1946 and placed on the market in 1957. It was re-registered in 1998 with the US EPA (Health and Environmental Protection Agency set up by President Richard Nixon in 1970 and very strict about product registration requirements). In 1999, insect olfactory receptors were identified and research into the molecular targets of DEET began (1). Insects use odour receptors, ionotropic receptors and gustatory receptors to smell the target. Some gustatory receptors detect carbon dioxide emitted by the body via the respiratory system, others are attracted to a broad spectrum of odourants. However, it is believed that there are many different sensory signals from humans that guide female mosquitoes as they feed on blood, an essential protein source for egg development.
Many scientific studies have used the mosquitoes Culex quinquefasciatus and Drosophila (also known as fruit flies) to understand the mechanism by which DEET disturbs the receptors of these insects, a mechanism that is still not fully elucidated.
Advantages and disadvantages of DEET
DEET repels insects, it is non-toxic, but some precautions must be taken to ensure repellency:
Alternatives to DEET
Nepeta cataria also called catnip, has shown some efficacy as a spatial repellent but less effective than DEET as a contact repellent (2).
VUAA1, a chemical compound that functions as a co-receptor ion channel agonist of the insect odour receptor (3).
Repellents of natural and plant origin such as Icaridin (picaridin;1-(1-Methylpropoxycarbonyl)-2-(2-hydroxyethyl)piperidine) and cinnamon oil have shown repellency almost equal to DEET, while margosa extract (Azadirachta indica (A.Juss., Sapindales: Meliaceae) has slightly lower efficacy (4). Other repellents: lemon eucalyptus oil, citronella oil, catnip oil and 2-undecanone, para-menthane-3,8-diol (distilled from Eucalyptus citriodora), geraniol.
Other uses
Used in pharmaceutical intermediates, anhydrides and salts. Compounds labelled with isotopes.
Solvent for dissolving plastics, synthetic fabrics such as rayon, spandex and painted surfaces.
For more information:
Typical commercial product characteristics N,N-Diethyl-m-toluamide/DEET
Appearance | Colorless or light yellow transparent liquid |
Boiling Point | 297.5±0.0°C at 760 mmHg |
Melting Point | -45ºC |
Flash Point | 141.7±13.3°C |
Density | 1.0±0.1 g/cm3 |
PSA | 20.31000 |
Vapor Pressure | 0.0±0.6 mmHg at 25°C |
Refraction Index | 1.517 |
LogP | 1.96 |
Acidity | 0.4ml (0.01NnaOH)/g 0.025mgNaOH/g |
Specific Gravity | 0.996-1.002 |
Water | ≤0.5% |
o-DEET | ≤0.30% |
p-DEET | ≤0.40% |
Diethyl amine,PPM | ≤10 |
Diethyl benzamide | ≤0.70% |
Trimethyl biphenyls | ≤1% |
N-Ethyl toluamide | ≤1.0% |
Safety |
Price
250 mg €45.50
Synonyms
References______________________________________________________________________
(1) Vosshall LB, Amrein H, Morozov PS, Rzhetsky A, Axel R. A spatial map of olfactory receptor expression in the Drosophila antenna. Cell. 1999 Mar 5;96(5):725-36. doi: 10.1016/s0092-8674(00)80582-6.
(2) Bernier UR, Furman KD, Kline DL, Allan SA, Barnard DR. Comparison of contact and spatial repellency of catnip oil and N,N-diethyl-3-methylbenzamide (deet) against mosquitoes. J Med Entomol. 2005 May;42(3):306-11. doi: 10.1603/0022-2585(2005)042[0306:cocasr]2.0.co;2.
(3) Rinker, D. C., Jones, P. L., Pitts, R. J., Rutzler, M., Camp, G., Sun, L., ... & Zwiebel, L. J. (2012). Novel high‐throughput screens of Anopheles gambiae odorant receptors reveal candidate behaviour‐modifying chemicals for mosquitoes. Physiological Entomology, 37(1), 33-41.
(4) Krüger A, Schmolz E, Vander Pan A. Methods for Testing Repellents Against Bed Bugs (Hemiptera: Cimicidae). J Econ Entomol. 2021 Feb 9;114(1):265-273. doi: 10.1093/jee/toaa304.
Sign up to vote this object, vote his reviews and to contribute to Tiiips.EvaluateClose | (0 comments) |
Read other Tiiips about this object in __Italiano (2)
Component type:   Chemical Main substances:   Toluic acid Last update:   2022-08-29 18:55:39 | Chemical Risk:   Irritant |