GB769613A - New n-(carbamyl) amides and compositions containing the same - Google Patents

New n-(carbamyl) amides and compositions containing the same

Info

Publication number
GB769613A
GB769613A GB760555A GB760555A GB769613A GB 769613 A GB769613 A GB 769613A GB 760555 A GB760555 A GB 760555A GB 760555 A GB760555 A GB 760555A GB 769613 A GB769613 A GB 769613A
Authority
GB
United Kingdom
Prior art keywords
carbon atoms
methyl
chlorocarbanilyl
carbanilyl
chloro
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB760555A
Inventor
Henry John Gerjovich
Rayner Selby Johnson
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co
Priority to GB760555A priority Critical patent/GB769613A/en
Publication of GB769613A publication Critical patent/GB769613A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/46Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylureas
    • C07C275/48Y being a hydrogen or a carbon atom
    • C07C275/50Y being a hydrogen or an acyclic carbon atom

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.
GB760555A 1955-03-15 1955-03-15 New n-(carbamyl) amides and compositions containing the same Expired GB769613A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB760555A GB769613A (en) 1955-03-15 1955-03-15 New n-(carbamyl) amides and compositions containing the same

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB760555A GB769613A (en) 1955-03-15 1955-03-15 New n-(carbamyl) amides and compositions containing the same

Publications (1)

Publication Number Publication Date
GB769613A true GB769613A (en) 1957-03-13

Family

ID=9836334

Family Applications (1)

Application Number Title Priority Date Filing Date
GB760555A Expired GB769613A (en) 1955-03-15 1955-03-15 New n-(carbamyl) amides and compositions containing the same

Country Status (1)

Country Link
GB (1) GB769613A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2361358A1 (en) * 1975-09-05 1978-03-10 Sandoz Sa NEW DERIVATIVES OF PHENYLURA THAT CAN BE USED FOR THE CONTROL AGAINST UNWANTED VEGETATION, AND THEIR PREPARATION

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2361358A1 (en) * 1975-09-05 1978-03-10 Sandoz Sa NEW DERIVATIVES OF PHENYLURA THAT CAN BE USED FOR THE CONTROL AGAINST UNWANTED VEGETATION, AND THEIR PREPARATION

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