Salicyl anilides

Very similar behaviour was found for salicylamide and salicyl-anilide (Schulman et al., 1973c) but 3- and 4-hydroxybenzoic acids showed no intra- or intermolecular phototautomerism, possibly because of the very short lifetimes of the Sj states involved. Also, the ionization sequences in the ground and lowest excited singlet states appear to be the same for these molecules and their methyl esters (Paul and Schulman, 1974). 

Salicylic anilide (SAN) has been investigated by Naboikin and co-workers (21). The spectral behavior of SAN is much more solvent dependent than that of MSA. 

Mildew. Mildew is the cause of rapid deterioration of cotton fabrics, particularly in the tropics. A variety of mildew-proofing chemicals are available, including salicyl anilide, pentachlorophenol, copper naphthenate, and copper 8-hydroxyquinolate. 

Many different protonophores, each with a different effectiveness, are available like 2,4-dinitrophenol (DNP) or 5-chloro-3-tert-butyl-2 -chloro-4 -nitro-salicyl-anilide (CCCP). Manipulation of the two components of the A/Ih can be effected with two potassium ionophores. Valinomycin increases the electrogenic permeability of a membrane for potassium and leads to the dissipation of the if a high concentration of potassium is present (more than 10 mM). Nigericin catalyzes an electroneutral potassium proton exchange and thus dissipates the A pH under the same conditions. In combination these two ionophores function as an uncoupler. 

As in the case of the membrane-active phenol derivatives (7.) the halogenation of salicylanilides or carbanilides increases the antimicrobial efficacy. The best results are obtained by means of di- to penta-chlorination or bromination, the halogen atoms being more or less evenly distributed on the two phenyl rings. On the other hand halogenated salicyl anilides have photosensitizing properties, which has reduced their practical importance. 

Salicyl-u-toluide has been prepared only by the action of phosphorus oxychloride upon a mixture of salicylic acid and o-toluidine. The useful methods of preparation of salicylanilide are by the interaction of salicylic acid and aniline in the presence of phosphorus trichloride, by heating phenyl salicylate and aniline, and from o-hydroxybenzamide and bromobenzene in the presence of small amounts of sodium acetate and metallic copper. A number of these and other anilides have been described. ... 

The fact that the presence of the hydroxy function originating from the salicylic acid is an essential requirement for cestodicidal and flukicidal activity, led Hoechst scientists to prepare a variety of 2,6-dihydroxybenzoic acid anilides. The most effective compound of the series were 4 -chloro/bromo-6-hydroxysalicy-lanilides (5a,b). Of these, the bromo analogue, called resorantel (terenol, 5b) was found to be more effective than the 4 -chloro analogue (5a) [12]. Resorantel was later... 

Salicylic acid (3) and aniline (4) are condensed in the presence of a catalyst at a raised temperature to salicylic acid anilide (2-hydroxy-N-phenylbenzamide). 

These toxic components of the coatings can be copper oxides (I), mercury, tin-bis(tributyl)oxide, barium metaborate, anilide of salicylic acid, phenols and their derivatives, compounds of aminoformic acids, etc. [87]. In the area of metal ion toxins copper protoxide, lead and tin derivatives have recently come into extensive use. 

Substances discovered by Gerhardt include cumene, cuminol as the aldehyde of cumic acid, and cymene, styrene, anilides, sulphanilic acid, acetanilide, and the anhydrides of monobasic organic acids (1852, see p. 454). He introduced the names phenol, borneol, and glucoside. After Laurent s work on phenol (see p. 389) Gerhardt prepared it by heating salicylic acid with lime and showed that it is not a true acid (acide phenisique) but is related to the alcohols. In his work on anilides he represented oxamide, which the discoverer Dumas had correctly formulated as an amide, + N H, as containing the imide group NH, viz. + = +... 

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