Patent GB-913383-A (GB)
Title: New carbamic acid derivatives and process for their manufacture
IPC: C07C275/36
Filed: 1960-07-29
Abstract: Compounds of the formula <FORM:0913383/IV (b)/1> in which R is H or an alkyl group of 1-4 carbon atoms, R1 and R2 each represents H, halogen, or an alkyl, trifluoromethyl, or alkoxy group, X is O or S, and n is 1, 2, or 3, are employed as active ingredients in herbicides.  Compounds of the general formula in which R is H or 1-4 C alkyl; X is O or S; R1 and R2 are H or halogen; and in which when X = oxygen, R1 and R2 may further represent alkoxy or trifluoromethyl, are claimed as new compounds.  The compounds may be obtained by various methods including the reaction of appropriate secondary amines with phenoxy phenyl isocyanates, carbamic chlorides or carbamic esters, and the reaction of appropriate phenoxy phenylamines with N-disubstituted carbamic chlorides or esters or with urea and secondary amines.  The compounds N - 4 - (phenoxy)-, N-4-(p-chlorophenoxy)-, N-4-(o, m, and p-cresoxy)-, N-4-(phenylthio)-, and N-4-(p-chlorophenylthio)-phenyl-N1.N1-dimethyl urea, and N-4-(phenoxy) - phenyl-N1-monomethyl urea are specifically claimed.  Many other compounds of the stated formula which may be used in herbicidal preparations are described. Specification 536,011 is referred to.ALSO:Compositions for controlling the growth of plants or killing weeds comprise as herbicide a compound of the formula <FORM:0913383/VI/1> where R is H or a C1-4 alkyl group, R1 and R2 each represents H or halogen or an alkyl, trifluormethyl or alkoxy group, X represents oxygen or sulphur, and n is 1, 2, or 3, in admixture with a solid or liquid carrier, an emulsifying agent, a dispersing agent, a fertilizer, or another herbicide or a pest combating agent.  Many compounds of the stated formula are mentioned, including N-4-(phenoxy)-, N-4-(p-chlorophenoxy) -, N - 4 - (o, m, and p - cresoxy) -, and N - 4 - (m - xylene oxy) - phenyl-N.N1 - dimethyl urea, N - 4 - (p - chlorophenylthio) - phenyl - N.N1 - dimethyl urea, and N-4 - (phenoxy) - 3 - trifluoromethylphenyl-N.N1-dimethyl urea. For making dusting powders solid carriers such as talcum, kaolin, bentonite, calcium carbonate or phosphate, carbon, cork meal, or wood meal may be used.  Liquid preparations may contain mineral oil fractions, kerosene, tar oils, vegetable or animal oils, hydrocarbons, chlorinated hydrocarbons, alcohols, and ketones. Aqueous preparations may be obtained by the addition of water to emulsion concentrates, pastes, or wettable powders. Anionic, cationic, or non-ionic dispersing agents may be used. Other weed-killing agents which may be present in the compositions include aryl-alkyl ureas, halogenated carboxylic acids and esters or amides of these, borax and other inorganic salts.  Calcium cyanamide, urea, or other fertilizers may be included. Chlorinated hydrocarbons or phosphoric esters may be present as pesticides.  Other optional ingredients include dodecyl hexamethylene imine, ethylene dipyridinium dibromide, carbamates, 2-chlorobenzthiazole, maleic hydrazide, pentachlorophenol, naphthylphthalamic acid, methyl isothiocyanate, and condensation products of ethylene oxide with soya bean fatty acid. Specification 536,011 is referred to.