GB771333A — Improvements relating to halogen substituted diphenyl urea and thiourea compounds and their use

USPTO Abstract

The invention comprises polyhalogen substituted phenyl ureas and thioureas of the formula <FORM:0771333/IV(b)/1> in which the benzene rings may contain further substituents, e.g. two further halogens but no water-solubilizing groups; and methods for preparing them by reaction of halogen-o-hydroxy-amino compounds with compounds introducing halogen-phenyl-carbamyl or thiocarbamyl radicals into the amino group. In examples, N-3 : 4-dichlorophenyl-N1-21-hydroxy-41-chlorophenyl urea is obtained from 3 : 4-dichlorobenzoic azide and the corresponding phenol; N-3 : 4-dichlorophenyl-N1-21-hydroxy-51 -chlorophenylurea is obtained from 3 : 4-dichlorophenylurea and the corresponding phenol; N - 3 : 4 - dichlorophenyl - N1 - 21 - hydroxy - 41 : 51 - dichlorophenyl urea is obtained from 3 : 4-dichlorophenylcarbamic acid phenyl ester and the corresponding phenol; N-4-chlorophenyl - N1 - 21 - hydroxy - 41 : 51 - dichlorophenylthiourea is obtained from 4-chlorophenyl isothiocyanate and the corresponding phenol; similar compounds containing bromine in the phenol molecule (Example (7)), and a trifluoromethyl group as in the formul (Examples (8) and (9)) are described; a table of the properties of a number of other similar products is given. Other methods of introducing the halogen phenyl carbamyl or thiocarbamyl radicle into the amino group include reaction of other substituted phenyl ureido compounds with suitable o-amino-hydroxy phenyl compounds; and a list of suitable phenyl iso and isothiocyanates for reacting with the amino group of the o-hydroxy amino compounds includes 4-bromophenyl, 4 - fluorophenyl -, dibromo and fluoro - chloro - isocyanates, and similar isothiocyanates.ALSO:As germicidal components of cleansing compositions, use is made of polyhalogen diphenyl ureas or thioureas of the formula <FORM:0771333/III/1> or <FORM:0771333/III/2> which may contain further substituents (see Group IV(b)). In an example, soap flakes are made up with N - 3:4 - dichlorophenyl - N1 - 21 - hydroxy - 41:51 - dichlorophenyl or - 31:41:51 - trichlorophenyl urea and perfume. These ureas may be included also in compositions containing non-ionic or anionic synthetic detergents.ALSO:A germicidal composition comprises polyhalogen phenyl ureas or thioureas of the formula <FORM:0771333/VI/1> which may contain further substituents (see Group IV(b)) in admixture with a cleansing agent such as soap or shampoo or incorporated in a cosmetic. In examples, (1) soap flakes are made up with N - 3 : 4 - dichlorophenyl N1 - 21 - hydroxy - 41 : 51 -dichlorophenyl or - 31 : 41 : 51 - tri-chlorophenyl - urea, and perfume, and pressed; and (2) a non ionogenic or anion active synthetic washing agent composition containing 10 per cent of one of these ureas, may give a 1 per cent aqueous cleansing solution suitable for linen.