Patent GB-834358-A (GB)
Title: N-monoaryl substituted carbamic acid 2, 4, 5-trichlorophenyl esters
IPC: D06M16/00
Filed: 1957-12-02
Abstract: An agent for combatting fungi contains a compound of the formula <FORM:0834358/III/1> where X is hydrogen, chlorine, methyl or a nitro group, together with an inert diluent or carrier.  The active compounds may be used as paint additives, e.g. for preventing growth on hulls of ships.ALSO:The invention comprises N-aryl carbamic acid 2:4:5-trichlorophenyl esters of the general formula <FORM:0834358/IV (b)/1> where X is hydrogen, chlorine or a methyl or nitro group.  The esters may be prepared by (a) treating an aromatic isocyanate with the chlorophenol, (b) treating an aromatic amine with the chloroformic ester of the chlorophenol, (c) treating a chloroformic anilide with the chlorophenol, or (d) treating an aromatic amine with the carbonic ester of the chlorophenol.  The compounds are found to be useful as fungicides (see Group VI).  In examples: (1) N-phenyl carbamic acid 2:4:5-trichlorophenyl ester is prepared from phenyl isocyanate and 2:4:5-trichlorophenol; (2) the N-m-tolyl compound is prepared from m-toluidine and chloroformic acid 2:4:5-trichlorphenyl ester; (3) the N-phenyl compound is prepared from chloroformic acid anilide and 2:4:5-trichlorophenol; (4) the N-phenyl compound is prepared from aniline and the carbonic acid ester of 2:4:5-trichlorophenol.ALSO:An agent for combating fungi suitable as a paint additive contains a compound of the formula <FORM:0834358/IV (a)/1> where X is hydrogen, chlorine, methyl or a nitro group, together with an inert diluent or carrier.  In Example 10 a mixture of air-drying oil-modified alkyd resin pigments and fillers is mixed with 8% by weight of N-p-tolyl carbamic acid 2,4,5-trichlorophenyl ester and the mixture ground and its consistency made suitable for a paint.ALSO:Fungicidal compositions comprise as active ingredient an N-monoaryl carbamic acid 2 : 4 : 5 trichlorophenyl ester of the general formula <FORM:0834358/VI/1> where X is hydrogen or chlorine or a methyl or nitro group together with an inert diluent or carrier. The composition may contain up to 95% by weight of the active ingredient, the p  remainder being solvents, sellers or other carriers.  The compounds are found to be particularly useful for combating slime-forming fungi in systems carrying aqueous organic substances, the activity of the N-phenyl compound is still noticeable at dilutions of upwards of 1 : 40,000, and the compounds may also be used for protecting wood, textiles, fur and paper, preparing antimykotic soaps and as an additive to paints. In the examples: (5) an emulsion is prepared using the N-phenyl compound with an alkyl polyethylene glycol and methanol; a spraying powder is prepared using kaolin and a mixture of fatty acids containing 8-20 carbon atoms and polyethyleneglycol sorbite oleate together with (6) the N-phenyl compound and (7) the N-p-nitrophenyl compound; (8) a powder is prepared using the N-phenyl compound together with kaolin and talc; (9) an emulsion concentrate is prepared using the N-phenyl compound together with cyclohexanone, xylene, a tallolester of oxethylene sorbite combined with a sulphonate and a hydrophillic oxethylene alkyl phenol: (11) an aerosol is prepared using the N-phenyl compound together with a deodorant, acetone, difluorodichloromethane, monofluorotrichloromethane and a mixture of propane and butane.