N-Diethyl-3-Methylbenzamide

DEET was discovered by researchers at the U.S. Department of Agriculture and patented by the U.S. Army in 1946 

N diethyl 3 methyl benzamide. Red atom is oxygen white atoms are hydrogen black atoms are carbon and blue atom is nitrogen. Gray stick indicates a double bond striped sticks show a benzene ring. 

DEET is made commercially by treating m-toluic acid (C6H4CH3C00H) with thionyl chloride (S0C12). The product of this reaction, m-toluoyl chloride (C6H4CH3C00C1) is then treated with diethylamine (C2H5)2NH) to obtain N.N-diethyl- 

Environmental Protection Agency (EPA) has estimated that more than two hundred million people around the 

The mechanism hy which DEET repels insects is not completely understood. Current theories suggest that the compound blocks receptors on a mosquito s antennae that help it to locate carbon dioxide and lactic acid, given off in skin perspiration and the breath. Lacking these chemical clues, insects are unable to locate their prey (humans and other animals). 

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Repellents are materials that affect insects and other organisms by disrupting their natural behavior of bloodseeking through biting of humans and animals, and are the first line of defense that can be readily used for this purpose (1). The best overall standard repellent is A/,N-diethyl-m-toluamide [134-62-3] (DEET), systematically named N,N-diethyl-3-methylbenzamide (1). 

CHEMICAL NAME = N,N-diethyl-3-methylbenzamide CAS NUMBER = 134-62-3 MOLECULAR FORMULA = C12H17NO MOLAR MASS =191.3 g/mol... 

Synonyms Detamide Autan I-Delphene Meta-delphene Black Flag Tabarad Delphene Dielt-amide Flypel Muskol Naugatuck Det Off 612 Plus Jungle plus Pellit BETA DET N,N-Diethyl-3-methylbenzamide N,N-Diethyl-m-toluamide Chemical/Pharmaceutical/Other Class Methyl benzamide repellent Chemical Structure ... 

Qiu H., H. W. Jun, and J. W. McCall. Pharmacokinetics, formulation, and safety of insect repellent N,N diethyl 3 methylbenzamide (DEET) a review. Journal of the American MoAquito Control AAAociation. March 1998 12 27. Also available online at http //www.ncbi.nlm.nih.go v/entrez/query.fcgi cmd= Retrieve db=PubMed list uids=9826i685 dopt=Citation (accessed on October 7, 2005). 

C9H12O2, Mr 152.19, oil, [0] +39.3° (CHCI3). A dialdehyde from the leaves of Vitex rotundifolia, Verben-aceae, with insecticidal activity. The leaves are traditionally used in Japan as a mosquito repellant. R. has the same activity against Ae[Pg.559]

CAS 134-62-3 EINECS/ELINCS 205-149-7 Synonyms Benzamide, N,N-diethyl-3-methyl DEET Delphene m-Delphene DET N,N-Diethyl-3-methylbenzamide Diethyl-m-toluamide N,N-Diethyltoluamide N,N-Diethyl-m-toluamide Metadelphene 3-Methyl-N,N-diethylbenzamide m-Toluic acid diethylamide... 

A,N-Diethyl-3-methylbenzamide (also called A/,A-diethyl-m-toluamide, or DEBT) is used in many insect repellants. Write its structure. 

Although it is not typically considered as an agricultural chemical, N,N-diethyl-3-methylbenzamide (DEBT) remains as an important insect repellent, especially for mosquitoes. About 200 million people use it every year and over 8 billion doses have been applied over the past 50 years [43]. Estimates are that DEBT is used by approximately 30% of the United States population [44]. 

U. Bernier, K. D. Furman, D. L. Kline, S. A. Allan, and D. R. Barnard, Comparison of contact and spatial repellency of catnip oil and N, N-diethyl-3-methylbenzamide (deet) against mosquitoes. Journal of... 

A preferred insect repellent is liquid A,A-diethyl-m-toluamide (A,Af-diethyl-3-methylbenzamide) for indoor or outdoor use. Other such chemicals include dimeth-ylphthalate, 2-ethyl-l,3-hexanediol, stabilene, indalone, di-Bu-phthalate, citronyl, alicyclic piperidines, permethrin, di-Bu-succinate, hexahydrodibenzofuran carboxaldehyde-butadiene-furfural copolymer, f-Bu-A,A-dimethyldithiocarbamate, 2-hydroxyethyl n-octyl sulfide, pyrethrins, diazinon (0,0-diethyl-0-[4-methyl-6-(propan-2-yl)pyrimidin-2-yl]-phosphorothioate), flMcar (2-methyl-2-(methylthio)-propanal-0-((methylamino)carbonyl)-oxime), pine oil, and anthrahydroquinones... 

Figure 4 Full-scan PrepStation-GC-MS of 50 ml of Meuse River water (B) without and (A) with spiking with 37 micropollutants at the 0.18 ig/L level 100 (ll out of the 300 il extract were injected. The inserts show the reconstructed-ion chromatograms of two characteristic masses of 1,3-dichlorobenzene (C), 2-methylthlobenzothlazole (D), and Musk G and T (E). Compounds detected (0.2 to 430 ng/1) in the nonspiked river water 2. 1,3-dichlorobenzene 2. 1.4-dichlorobenzene 2", 1,2 dichlorobenzene 3, acetophenone 4, decamethyl cyclopentasiloxane 6, naphthalene 10, isoquinoline 11, 2-methyl-qulnoline) 12, 2,4,7,9-tetramethyl-5-decyne-4,7-diol 13, dibenzofuran 14, tiiisobutyl phosphate 15, N,N liethyl-3-methylbenzamide 16, 2,2,4-trimethylpentane 1,3-dioldi-isobutyrate 17, diethyl phthalate 18, 2-methylthiobenzothiazole 20, tetraacetylethylene-diamlne 21, tributyl phosphate 22, ethyl citrate 23, desethylatrazine 25, simazine 26, atrazine 27, tris(2-chloroethyl)phosphate 28, 7V-butylbenzenesulfonamide 30, tris(2-chloroisopropyl)phosphate 31, Musk G 33, Musk T, (From Ref. 65.)...

Murphy, E. J., Booth, J. C., Davrazou, F., Port, A. M., and Jones, D. N. Interactions of Anopheles gambiae odorant-binding proteins with a human-derived repellent Implications for the mode of action of AAf-diethyl-3-methylbenzamide (DEET). J Biol Chem 288,4475-4485 (2013). 

By the alkylation of N-benzoyl uracil with the chiral 2-trityloxy-oxirane was obtained glycoside-like derivative N-[l-(2-hydroxy-3-trityloxy-propyl)-2-oxo-l,2-dihydroxypyrimidin-4-yl]-N-methylbenzamide as a single isomer. From N-[1-(2-hydroxy-3-trityloxy-propyl)-2-oxo-l,2-dihydroxypyrimidin-4-yl]-N-methylbenzamide and toluene-(4-sulfomethyl)phosphonic acid diethyl ester was prepared [2-[(benzoylmethylamino)-2-oxo-2H-pyrimidin-l-yl]-l-trityloxymethylethoxymethyljphosphonic acid diethyl ester. As a result of... 

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