Toluamides—

Repellents are materials that affect insects and other organisms by dismpting 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/,A/-diethyl-y -toluamide [134-62-3] (DEBT), systematically named A/jAZ-diediji-S-methylbenzamide (1). 

EPA JV,IV-Diethyl-m-toluamide (DEFT), Pesticide Registration Standard, U.S. EPA, Washington, D.C., 1980. 

A uV-Diethyl-m-toluamide (DEET) is the active ingredient in many insect-repellent preparations. Plow might you synthesize this substance from m-bromotoluene ... 

The lithio derivative of Ar,Ar-dicthyl-2-toluamide 1 adds to each enantiomerically pure glycer-aldehyde acetonide 4-methoxybenzyl imine [(7 )-2 or (S)-2] to provide only one diastereomer exclusively or (3/ ,TA)-3, respectively]. The moderate yield (50%) is due. in part,... 

As a part of the total synthesis of (+ )-corydalic acid methyl ester (12), a reaction of a cyclic enolate with an imine has been applied. The 2-toluamide enolate 9, which in this case is substituted at the methyl group, adds stereospecifically to imine 10, affording mainly tram-iso-quinolone 11 with a d.r. (transjds) > 95 525. 

A derivative of benzylhydrazine, procarbazine (8), exhibits antineoplastic activity. In an interesting insertion-type sequence, reaction of the p-toluamide (5) with ethyl azodicarboxylate leads directly to the substituted hydrazine (6). It is not unlikely that the first mole of the diazo compound... 

Additions of stabilized carbanions to imines and hydrazones, respectively, have been used to initiate domino 1,2-addition/cyclization reactions. Thus, as described by Benetti and coworkers, 2-subshtuted 3-nitropyrrolidines are accessible via a nitro-Mannich (aza-Henry)/SN-type process [165]. Enders research group established a 1,2-addition/lactamization sequence using their well-known SAMP/ RAMP-hydrazones 2-308 and lithiated o-toluamides 2-307 as substrates to afford the lactams 2-309 in excellent diastereoselectivity (Scheme 2.72) [166]. These compounds can be further transformed into valuable, almost enantiopure, dihydro-2H-isoquinolin-l-ones, as well as dihydro- and tetrahydroisoquinolines. 

Fenvalerate toxicity is antagonized by atropine sulfate or methocarbamol, which may be effective in treating severe cases of poisoning (Hiromori et al. 1986). Conversely, some compounds exacerbate the toxicity of fenvalerate and interfere with a desired use. Domestic cats (Felis domes-ticus) treated with Fendeet (an aerosol mixture of fenvalerate and A-A-diethyl-m-toluamide) to control fleas and ticks sometimes show signs of toxicosis, such as tremors, hypersalivation, ataxia, vomiting, depression, and seizures. Signs usually appeared within hours of topical application, and females and juveniles seem to be the most sensitive groups. The demonstrated ability of N-N-diethyl-m-toluamide to enhance the dermal absorption of fenvalerate is the probable cause of toxicosis (Dorman et al. 1990). 

Topical aerosol treatment of fenvalerate plus Deet (N-N-diethyl-m-toluamide) to control fleas and ticks... 

Dorman, D.C., W.B. Buck, H.L. Trammel, R.D. Jones, and V.R. Beasley. 1990. Fenvalerate/AQV-diethyl-m-toluamide (Deet) toxicosis in two cats. Jour. Amer. Veterin. Med. Assoc. 196 100-102. 

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