Patent GB-769613-A (GB)
Title: New n-(carbamyl) amides and compositions containing the same
Inventor: GERJOVICH HENRY JOHN
IPC: C07C275/50
Filed: 1955-03-15
Abstract: The invention comprises compounds of the formul <FORM:0769613/IV(b)/1> and <FORM:0769613/IV(b)/2> wherein A and R are the same or different and are a hydrogen or halogen atom or the group R1 or OR11, where R1 is an alkyl group of less than 5 carbon atoms and R11 is an alkyl or alkenyl group of less than 5 carbon atoms, E is a halogen atom or the group R1 or OR11 as hereinbefore defined, n is 1 or 2, L, M and Q each are a hydrogen atom, a formyl radical, or an aliphatic hydrocarbon radical of less than 5 carbon atoms, with the proviso that one and only one of L, M and Q is formyl, and at least one but not more than two of L, M and Q is an aliphatic hydrocarbon radical; and X, Y and Z each represent a hydrogen atom, an alkanoyl or alkenoyl radical of 2-4 carbon atoms inclusive, or an aliphatic hydrocarbon radical of less than 5 carbon atoms, with the proviso that one and only one of X, Y and Z is alkanoyl or alkenoyl, and at least one but not more than two of X, Y and Z is an aliphatic hydrocarbon radical.  The alkanoyl substituent may be substituted, especially with halogen to give radicals such as mono-, di-, or tri-chloroacetyl.  The compounds may be prepared by reacting an amide with an isocyanate or carbamyl halide, preferably in an inert solvent such as xylene, toluene or dioxane at a temperature of about 15 DEG to 75 DEG  C. and using a slight excess of amide.  Compounds specifically described are N(carbanilyl)-or -(o-, m-, or p-chlorocarbanilyl)- or -(3 : 4-dichlorocarbanilyl)- or -(2 : 4 : 5-trichlorocarbanilyl)- or -(p-bromocarbanilyl)- or -(m- or p-methylcarbonilyl)- or -(3 : 4-dimethylcarbanilyl)- or -(p-isopropyl- or -sec.-butyl-carbanilyl)-or -(3- or 4-chloro-3- or -4-methyl-carbanilyl)- or -(3-chloro-4-methoxy-carbanilyl)- or -(4-allyloxy - 3 - chlorocarbanilyl) - or - (p - chloro - N1 - methylcarbanilyl) - N - methylformamide, N - (m- or p-chlorocarbanilyl)- or -(3 : 4-dichloro- or 2 : 4 : 5 - trichloro - carbanilyl) - N - methylacetamide, N - (p - chloro - carbanilyl) - N - methylpropionamide, N - (3 : 4 - dichlorocarbanilyl) - N - methylbutyramide, N - (p - chlorocarbanilyl) - N - methylisobutyramide, N - (p - chlorocarbanilyl) - N - methyl - a  : a : a  - trichloroacetamide, N - (3 : 4 - dichlorocarbanilyl) - N - methylacrylamide, N - (4 - chloro - or 3 : 4 - dichlorocarbanilyl) - N - ethylformamide, N - (4 - chloro - or 3 : 4 - dichlorocarbanilyl)- or -(carbanilyl)-N-isopropylformamide, N - (3 : 4 - dichlorocarbanilyl) - N - butylformamide, N - (p - chlorocarbanilyl) - N - ethylacetamide, N - (methyl - or dimethyl - carbamyl) - 3 : 4 - dichloroformanilide, N - (methylcarbamyl) - p - chloroacetanilide, N - (methyl - or ethyl- or dimethyl - carbamyl)-formanilide, p-chloro - N - (ethyl - or dimethyl - carbamyl) formanilide and 3-methyl- or 3-chloro-4-methyl - N - (methylcarbamyl) formanilide.  The compounds are used in herbicidal compositions (see Group VI).  In examples: (1) 3 : 4-dichlorophenyl isocyanate or p-chlorophenyl isocyanate and N-methylformamide were reacted to give N-(3 : 4-dichlorocarbanilyl)-N-methylformamide and N-(p-chlorocarbanilyl-N-methylformamide; (2) methyl isocyanate and 3 : 4-dichloroformanilide were reacted to give N-(methylcarbamyl) - 3 : 4 - dichloroformanilide. 3 : 4-dichlorophenyl isocyanate was prepared by reacting 3 : 4-dichloroaniline and phosgene in a xylene solution.ALSO:Herbicidal compositions comprise at least one compound of formula:- <FORM:0769613/VI/1> wherein A and R are the same or different and are a hydrogen or halogen atom or the group R1 or OR11 where R1 is an alkyl group of less than 5 carbon atoms and R11 is an alkyl or alkenyl group of less than 5 carbon atoms, E is a halogen atom or the group R1 or OR11 as hereinbefore defined, n is 1 or 2, L, M and Q each are a hydrogen atom, a formyl radical, or an aliphatic hydrocarbon radical of less than 5 carbon atoms, with the proviso that one and only one of L, M and Q is formyl, and at least one but not more than two of L, M and Q is an aliphatic hydrocarbon radical; and X, Y and Z each represent a hydrogen atom, an alkanoyl or alkenoyl radical of 2-4 carbon atoms inclusive, or an aliphatic hydrocarbon radical of less than 5 carbon atoms, with the proviso that one and only one of X, Y and Z is alkanoyl or alkenoyl and at least one but not more than two of X, Y and Z is an aliphatic hydrocarbon radical (see Group IV(b)), together with an inert diluent.  Many compounds are specified, for example, N-(carbanilyl)-N-methylformamide, N - (p - chloro- or - bromo- or - methyl - carbanilyl) - N - methylformamide, N - (p-chlorocarbanilyl) - N - methylpropion amide, N - (p - chlorocarbanilyl) - N - methyl - a : a : a  - trichloroacetamide, N - (3:4 -dichlorocarbanilyl) - N - butylformamide, N - (methylcarbamyl) formanilide and N - (methylcarbamyl) - p - chloroacetanilide.  Specified solid diluents are talcs, natural clays, pyrophyllite, diatomaceous earth, dextrin, gelatin and walnut shell, wheat, redwood, soya bean and cottonseed flours.  Specified liquid diluents are kerosene, cottonseed oil, alkylated naphthalenes, dimethyformamide and cresols.  Specified surface active and/or dispersing agents used in the compositions are sodium and potassium oleates, morpholine and dimethylamine oleates, sulphonated fish or castor or petroleum oils or acyclic hydrocarbons, sodium lignin sulphonate, alkylnaphthalene sodium sulphonate, sodium salts of sulphonate condensation products of naphthalene and formaldehyde, sodium lauryl sulphate, sodium disulphonate of dibutyl phenylphenol, disodium monolauryl phosphate, sorbitol laurate, pentaerythritol or glycerol monostearate, diglycol oleate, polyethylene oxides, ethylene oxide condensation products with stearyl alcohol or octylphenol, polyvinyl alcohols, methyl cellulose, acetate of polyamines from the reductive amination of ethylene/carbon monoxide polymers, laurylamine hydrochloride, laurylpyridinium bromide, stearyl trimethylammonium bromide, cetyldimethylbenzyl ammonium chloride and lauryldimethylamine oxide.