GB728098A - Improvements relating to salicylanilides and their use - Google Patents

Abstract

The invention comprises salicylanilides of the formula <FORM:0728098/IV (b)/1> wherein R represents an alkyl radical with from 4-12 carbon atoms; Hal represents halogen; X represents hydrogen or alkyl; Y represents hydrogen or halogen, and Z represents hydrogen, halogen or the trifluoro-methyl group. These compounds may be prepared by reacting 5-alkyl-2-hydroxybenzoic acids, their acid halides or 2-acyloxy analogues (in which the alkyl group contains from 4-12 carbon atoms, and which can be substituted in the 3-position by another alkyl group), with 4-halogen-1-amino benzene compounds (which may be further substituted by a trifluoromethyl group in the 3-position or by a further halogen preferably ortho to the 4-halogen atom), and then saponifying any acyloxy group present under mild conditions. The compounds may be prepared by heating the appropriate o-hydroxybenzoic acid with the halogen aniline in an organic solvent (toluene, chlorobenzene, nitrobenzene) with a dehydrating agent (phosphorus tri-chloride, thionyl chloride or aluminium chloride). In an example 5-tert.-amylsalicylic acid and p-chloraniline are boiled in chlorobenzene with aluminium chloride and phosphorus trichloride, mixture neutralized and solvent steam-distilled leaving 5-tert.-amylsalicylic acid-41-chloranilide. Numerous other salicylanilides are listed, derived from 5-tert.-butyl-, 5-tert.-amyl-, 5-iso-octyl-, and 3 : 5-ditert.-amyl-salicylic acid; 5-tert.-butyl- and 5-n-amyl-o-cresotic acid; and 3 : 4-dichloro-; 3 : 4 : 5-trichloro-; 3-trifluoromethyl-4-chloro; 2 : 4 : 5 - trichloro-; 2 : 4 - dibromo-; p-chloro- and p-bromo-aniline.ALSO:Salicylanilides of the general formula <FORM:0728098/VI/1> (wherein R is an alkyl radical containing from 4-12 carbon atoms; Hal is halogen; X is hydrogen or alkyl; Y is hydrogen or halogen; and Z is hydrogen, halogen or the trifluoromethyl group) are used for proofing organic materials against fungi and rot, or as disinfectants and fungicides. They can be used alone or with auxiliary agents such as wetting or cleaning agents, or in organic solution, in particular with fungistatic agents, e.g. copper and mercury compounds. Many salicylanilides are specified (see Group IV (b)).