GB789445A - Carboxy-alkyl n-substituted phenyl carbamate and herbicidal compositions thereof - Google Patents
Carboxy-alkyl n-substituted phenyl carbamate and herbicidal compositions thereofInfo
- Publication number
- GB789445A GB789445A GB15520/54A GB1552054A GB789445A GB 789445 A GB789445 A GB 789445A GB 15520/54 A GB15520/54 A GB 15520/54A GB 1552054 A GB1552054 A GB 1552054A GB 789445 A GB789445 A GB 789445A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxy
- esters
- phenyl
- specified
- group
- 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
Links
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/20—N-Aryl derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises compounds having the formula: <FORM:0789445/IV (b)/1> wherein R is an alkylene or halogenated alkylene group, X is a hydrogen atom or an alkyl, cycloalkyl or phenyl group, Y is a halogen atom or an alkyl, alkoxy, cyano or nitro group, and n is 1-5, and esters, salts or amides thereof, Y also being hydrogen in the case of the aralkyl esters. The compounds are used in herbicidal compositions (see Group VI). The compounds are prepared by reacting a phenyl isocyanate with an ester of an hydroxy-aliphatic carboxylic acid, whereby compounds of the above formula wherein X is hydrogen are prepared, or by reaction of a phenyl amine, having at least one hydrogen atom linked to its nitrogen atom, with the haloformate of an ester of an hydroxy-aliphatic carboxylic acid. The phenyl isocyanates are prepared by reacting a phenyl amine with a carbonyl halide, preferably phosgene. The haloformates are prepared by reacting a carbonyl halide, such as phosgene or carbonyl bromide, with an hydroxy-aliphatic carboxylic acid ester, preferably by the method described in Specification 624,604. The free acids may be obtained from the ester products by hydrolysis and may be converted into salts of metals such as lithium, sodium, potassium, rubidium, caesium, strontium and barium, or salts of ammonia and amines such as mono- or tri-methylamine, diethylamine, mono- or triethanolamine and isopropanolamine. The amides are prepared by ammonolysis of the esters in known manner. Specified acids, which in the form of their esters may be used in the process of the invention, are glycollic, lactic, a -or b - or g -hydroxybutyric, a -hydroxy-b -chlorobutyric, b -chloro-lactic, acetonic, hydroxycaproic acids such as leucic, a -hydroxy-valeric, a - or b -hydroxy-isovaleric, a -hydroxy-caprylic, tetramethyl-hydracrylic and hydroxy-stearic acids. Specified esters are esters of lactic acid with alcohols having 1-30 carbon atoms, cyclohexyl lactate, benzyl lactate, 2-chloroethyl lactate, methyl and ethyl glycollates and ethyl a - hydroxy - isobutyrate. Specified primary amines are chloroanilines having 1-5 chlorine atoms and the corresponding bromine, fluorine and iodine compounds, mixed haloanilines such as chlorofluoroanilines, methylanilines having 1-5 methyl groups, ethyl- or propyl- or isopropyl-anilines, 4-methyl-5-ethylaniline, aminoanisoles, 2 : 5-dimethoxyaniline, polymethoxyanilines, 4 - amino - 3 - chloro - toluene, 2-amino - 4 - chlorotoluene and 2 - chloro - 5-methoxy-aniline. Specified secondary amines are diphenylamine and N-methyl-, ethyl-, propyl- or butyl-aniline. The secondary amines must be substituted in the nucleus as specified above except when the aryl esters are prepared. In examples: (1) m-chloroaniline was reacted in benzene solution with alpha-carbobutoxyethyl chloroformate to give alpha-carbobutoxyethyl 3-chlorophenylcarbamate which was hydrolysed with aqueous sodium hydroxide to give alpha-carboxyethyl 3-chlorophenyl carbamate; (2) 3-nitro- or methyl-phenyl isocyanate was reacted with n-butyl lactate to give alphacarbobutoxyethyl-3-nitro- or methylphenylcarbamate; (3) phenyl isocyanate and benzyl lactate were reacted to give alpha-carbobenzoxy-ethyl phenyl carbamate; (4) m-aminobenzonitrile or p-cresidine was reacted with alpha-carbobutoxyethyl chloroformate to give alpha-carbobutoxyethyl 3 - cyanophenyl - or 2 - methoxy-5-methylphenyl-carbamate.ALSO:Herbicidal compositions comprise compounds having the formula <FORM:0789445/VI/1> wherein R is an alkylene or halogenated alkylene group, X is a hydrogen atom or an alkyl, cycloalkyl or phenyl group, Y is a halogen atom or an alkyl, alkoxy, cyano or nitro group and n is 1-5, and esters, salts and amides thereof, Y also being hydrogen in the case of the aralkyl esters (see Group IV (b), dissolved in an inert solvent or dispersed in a solid carrier. Specified solvents are xylene, toluene, gasoline, kerosine, methanol, ethanol, ethers and ketones. Certain of the salts are water-soluble. Inorganic silicates are specified as solid carriers. Specification 624,604, [Group IV (b)], is referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US789445XA | 1953-05-26 | 1953-05-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB789445A true GB789445A (en) | 1958-01-22 |
Family
ID=22147163
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB15520/54A Expired GB789445A (en) | 1953-05-26 | 1954-05-26 | Carboxy-alkyl n-substituted phenyl carbamate and herbicidal compositions thereof |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB789445A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1297093B (en) * | 1959-11-17 | 1969-06-12 | Rhone Poulenc Sa | Carbamic acid esters and their use as herbicides |
JP2020529405A (en) * | 2017-07-31 | 2020-10-08 | ノッドセラ リミテッド | Selective NLRP3 inflammasome inhibitor |
-
1954
- 1954-05-26 GB GB15520/54A patent/GB789445A/en not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1297093B (en) * | 1959-11-17 | 1969-06-12 | Rhone Poulenc Sa | Carbamic acid esters and their use as herbicides |
JP2020529405A (en) * | 2017-07-31 | 2020-10-08 | ノッドセラ リミテッド | Selective NLRP3 inflammasome inhibitor |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
GB1353179A (en) | Hydantoin derivatives processes for producing them and compositions containing them | |
GB780193A (en) | Phenthiazine derivatives and processes for the preparation | |
GB953519A (en) | A process for the production of dithiazine compounds | |
GB1094205A (en) | Process for the preparation of amino-acid surface active agents | |
GB789445A (en) | Carboxy-alkyl n-substituted phenyl carbamate and herbicidal compositions thereof | |
GB849794A (en) | Mixtures of urea derivatives and phenyl carbamic acid esters suitable as herbicidal compositions | |
GB1121110A (en) | Carbamoyloximes | |
GB872313A (en) | Fluorine-containing derivatives of 1,3,5-triazine | |
GB1256530A (en) | ||
GB1080807A (en) | Heterocyclic amino-isobutyl compounds | |
US3683026A (en) | Trisubstituted hydrazines | |
GB1047061A (en) | Polymers and a process for the preparation thereof | |
GB1141183A (en) | Aliphatic mercaptoanilides and their use as herbicides | |
GB1138530A (en) | 2-phenylamino-2-oxazolines and their production | |
GB1055786A (en) | Urea derivatives | |
JPS5626873A (en) | Novel nnaminoalkylindole derivative* its manufacture and gastroointestinal tract movement trouble treating drug containing it | |
GB1071507A (en) | Substituted ureas and herbicidal compositions containing them | |
US2467893A (en) | Piperazine carboxamides and method of preparing same | |
GB1018308A (en) | Novel dichlorophenyl-substituted amides,thioamides,imidates and amidines,and herbicidal compositions containing them | |
GB567353A (en) | Improvements in the manufacture of tetrazole compounds | |
GB847205A (en) | A process for the manufacture of ethylenimine derivatives and novel ethylenimine derivatives | |
GB1384486A (en) | N-alkyl-n-o-tolylanthranilonitriles and their use in the preparation of 5-alkyl-10-amino-dihydrodibenzoazepines | |
GB1064525A (en) | Process of preparing new isophthalic acid derivatives | |
DE1130803B (en) | Process for the production of ketourethanes | |
GB920755A (en) | Basically substituted phenyl-thiocarbamic acid-s-esters |