ES476140A1 - Herbicidally active chloracetanilides, a process for their manufacture and their use - Google Patents
Herbicidally active chloracetanilides, a process for their manufacture and their useInfo
- Publication number
- ES476140A1 ES476140A1 ES476140A ES476140A ES476140A1 ES 476140 A1 ES476140 A1 ES 476140A1 ES 476140 A ES476140 A ES 476140A ES 476140 A ES476140 A ES 476140A ES 476140 A1 ES476140 A1 ES 476140A1
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- general formula
- formula
- optionally
- halogen
- 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
- 238000000034 method Methods 0.000 title abstract 3
- VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical class ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 3
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 150000002431 hydrogen Chemical class 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001448 anilines Chemical class 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
- A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (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
Procedimiento para la preparación de cloroacetanilidas de la fórmula general I **fórmula** en la que R1,R2 y R3 son iguales o distintos y representan hidrógeno, alcohilo C1-C4, halógeno o trifluorometilo, R4 representa alcohilo C1-C6, y n representa los número 1, 2 ó 3, ó en donde R1 y R2 son iguales o distintos y significan alcohilo C1-C4, R3 significa hidrógeno, R4 significa alcohilo C1-C4 y n significa los números 1 ó 2, caracterizado porque se hacen reaccionar anilinas de la fórmula general **fórmula** con compuestos de la fórmula general X-CH2CH2-(OCH2CH2)n-OR4 III en una proporción ponderal molar de preferiblemente 2:1 hasta 3:1, llevándose a cabo la reacción, en el caso de que X sea= hidroxilo, bajo presión eventualmente con adición de agua y de un catalizador, preferiblemente de un catalizador de níquel, y en el caso de que X sea=halógeno o el grupo 4-CH3.C6H4-SO2-O, a temperaturas de 20 a 200ºC eventualmente con utilización de un disolvente inerte, y los productos de reacción formados de la fórmula general. **fórmula** se hacen reaccionar con cloruro de cloroacetilo en proporciones ponderales equimolares, preferiblemente con un exceso de cloruro de cloroacetilo, en presencia de un aceptador de ácidos y eventualmente de un disolvente orgánico a temperaturas de -10º a 105ºC para formar los deseados productos del procedimiento, y éstos se aislan de modo en si conocido, teniendo R1,R2,R3,R4 y n los significados arriba expuestos.Process for the preparation of chloroacetanilides of the general formula I **formula** in which R1, R2 and R3 are the same or different and represent hydrogen, C1-C4 alkyl, halogen or trifluoromethyl, R4 represents C1-C6 alkyl, and n represents the numbers 1, 2 or 3, or where R1 and R2 are the same or different and mean C1-C4 alkyl, R3 means hydrogen, R4 means C1-C4 alkyl and n means the numbers 1 or 2, characterized in that anilines of the general formula **formula** with compounds of the general formula X-CH2CH2-(OCH2CH2)n-OR4 III in a molar weight ratio of preferably 2:1 to 3:1, the reaction being carried out, in the case of that X is= hydroxyl, under pressure, optionally with the addition of water and a catalyst, preferably a nickel catalyst, and in the case that X is=halogen or the group 4-CH3.C6H4-SO2-O, at temperatures from 20 to 200°C, optionally using an inert solvent, and the reaction products formed from the general formula. **formula** are reacted with chloroacetyl chloride in equimolar weight proportions, preferably with an excess of chloroacetyl chloride, in the presence of an acid acceptor and optionally an organic solvent at temperatures from -10º to 105ºC to form the desired products of the process, and these are isolated in a manner known per se, R 1 , R 2 , R 3 , R 4 and n having the meanings stated above.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782803662 DE2803662A1 (en) | 1978-01-25 | 1978-01-25 | CHLORACETANILIDES, METHOD FOR PRODUCING THESE COMPOUNDS AND HERBICIDES CONTAINING THEM |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES476140A1 true ES476140A1 (en) | 1979-05-01 |
Family
ID=6030587
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES476140A Expired ES476140A1 (en) | 1978-01-25 | 1978-12-19 | Herbicidally active chloracetanilides, a process for their manufacture and their use |
Country Status (37)
| Country | Link |
|---|---|
| JP (1) | JPS54106437A (en) |
| AR (1) | AR229464A1 (en) |
| AT (1) | AT363275B (en) |
| AU (1) | AU518222B2 (en) |
| BE (1) | BE873708A (en) |
| BG (1) | BG30163A3 (en) |
| BR (1) | BR7900426A (en) |
| CA (1) | CA1100996A (en) |
| CH (1) | CH640214A5 (en) |
| CS (1) | CS202520B2 (en) |
| DD (1) | DD141448A5 (en) |
| DE (1) | DE2803662A1 (en) |
| DK (1) | DK542378A (en) |
| EG (1) | EG13684A (en) |
| ES (1) | ES476140A1 (en) |
| FI (1) | FI790133A7 (en) |
| FR (1) | FR2415624A1 (en) |
| GB (1) | GB2013188B (en) |
| GR (1) | GR72999B (en) |
| HU (1) | HU176616B (en) |
| IE (1) | IE48057B1 (en) |
| IL (1) | IL56451A (en) |
| IN (1) | IN150409B (en) |
| IT (1) | IT1110982B (en) |
| LU (1) | LU80683A1 (en) |
| MX (1) | MX5406E (en) |
| NL (1) | NL7811673A (en) |
| NO (1) | NO150039C (en) |
| NZ (1) | NZ189424A (en) |
| PL (1) | PL112862B1 (en) |
| PT (1) | PT69111A (en) |
| RO (1) | RO76590A (en) |
| SE (1) | SE7900647L (en) |
| SU (2) | SU1149858A3 (en) |
| TR (1) | TR20274A (en) |
| YU (1) | YU304478A (en) |
| ZA (1) | ZA79319B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4731109A (en) * | 1980-03-25 | 1988-03-15 | Monsanto Company | Herbicidal 2-haloacetanilides |
| LU83232A1 (en) * | 1980-03-25 | 1981-10-30 | Monsanto Co | 2-HALOACETANILIDES HERBICIDES AND COMPOSITIONS CONTAINING THEM AS ACTIVE INGREDIENTS |
| EP0174278B1 (en) * | 1984-09-03 | 1989-04-19 | Ciba-Geigy Ag | N-(substituted-alkyl) dichloroacetamide derivatives |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3547620A (en) | 1969-01-23 | 1970-12-15 | Monsanto Co | N-(oxamethyl)alpha-halo-acetanilide herbicides |
| GB1407205A (en) * | 1971-09-17 | 1975-09-24 | Girling Ltd | Vehicle braking systems |
| JPS5614083B2 (en) * | 1972-02-07 | 1981-04-02 | ||
| DD112988A5 (en) * | 1972-06-06 | 1975-05-12 |
-
1978
- 1978-01-25 DE DE19782803662 patent/DE2803662A1/en not_active Withdrawn
- 1978-11-28 NL NL7811673A patent/NL7811673A/en not_active Application Discontinuation
- 1978-11-30 DK DK542378A patent/DK542378A/en not_active Application Discontinuation
- 1978-12-04 IN IN873/DEL/78A patent/IN150409B/en unknown
- 1978-12-15 AR AR274824A patent/AR229464A1/en active
- 1978-12-19 ES ES476140A patent/ES476140A1/en not_active Expired
- 1978-12-20 LU LU80683A patent/LU80683A1/en unknown
- 1978-12-22 YU YU03044/78A patent/YU304478A/en unknown
-
1979
- 1979-01-08 MX MX797634U patent/MX5406E/en unknown
- 1979-01-11 IT IT19218/79A patent/IT1110982B/en active
- 1979-01-11 BG BG042036A patent/BG30163A3/en unknown
- 1979-01-15 GB GB7901378A patent/GB2013188B/en not_active Expired
- 1979-01-16 FI FI790133A patent/FI790133A7/en unknown
- 1979-01-16 JP JP230079A patent/JPS54106437A/en active Granted
- 1979-01-18 CS CS79410A patent/CS202520B2/en unknown
- 1979-01-18 IL IL56451A patent/IL56451A/en unknown
- 1979-01-18 NZ NZ189424A patent/NZ189424A/en unknown
- 1979-01-19 CA CA319,949A patent/CA1100996A/en not_active Expired
- 1979-01-22 PT PT7969111A patent/PT69111A/en unknown
- 1979-01-23 EG EG45/79A patent/EG13684A/en active
- 1979-01-23 DD DD79210593A patent/DD141448A5/en unknown
- 1979-01-23 RO RO7996564A patent/RO76590A/en unknown
- 1979-01-23 PL PL1979212939A patent/PL112862B1/en unknown
- 1979-01-24 BR BR7900426A patent/BR7900426A/en unknown
- 1979-01-24 AT AT0050579A patent/AT363275B/en not_active IP Right Cessation
- 1979-01-24 AU AU43613/79A patent/AU518222B2/en not_active Ceased
- 1979-01-24 HU HU79SCHE671A patent/HU176616B/en unknown
- 1979-01-24 SE SE7900647A patent/SE7900647L/en not_active Application Discontinuation
- 1979-01-24 TR TR20274A patent/TR20274A/en unknown
- 1979-01-24 NO NO790230A patent/NO150039C/en unknown
- 1979-01-24 GR GR58173A patent/GR72999B/el unknown
- 1979-01-25 SU SU792715499A patent/SU1149858A3/en active
- 1979-01-25 BE BE0/193074A patent/BE873708A/en not_active IP Right Cessation
- 1979-01-25 ZA ZA79319A patent/ZA79319B/en unknown
- 1979-01-25 CH CH77479A patent/CH640214A5/en not_active IP Right Cessation
- 1979-01-25 FR FR7901877A patent/FR2415624A1/en active Granted
- 1979-01-25 SU SU792713492A patent/SU886736A3/en active
- 1979-01-30 IE IE127/79A patent/IE48057B1/en unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3784635A (en) | Substituted phenoxybenzoic acids and esters thereof | |
| ES483767A1 (en) | PROCEDURE FOR PRODUCING N-ARYLSULFONYL-L-ARGININAMIDES | |
| ES8500727A1 (en) | Phenylethylemine derivatires as growth stimulators. | |
| ES8301978A1 (en) | 2-Guanidino-4-heteroarylthiazoles and pharmaceutical compositions containing them. | |
| ES8307824A1 (en) | New cephem compounds and processes for preparation thereof. | |
| ES8301926A1 (en) | 9-Amino-1-hydroxyoctahydrobenzo(c)quinolines and derivatives thereof. | |
| ES476140A1 (en) | Herbicidally active chloracetanilides, a process for their manufacture and their use | |
| ES8305345A1 (en) | Carboxylic acid derivatives, their preparation and use as pharmaceuticals. | |
| US4002662A (en) | 2-Nitro-5-(cyano-trifluoromethyl-phenoxy)benzoic acids and esters | |
| ES8704468A1 (en) | PROCEDURE FOR PREPARING NEW 1,2,4-TRIAZOLE-CARBAMATES | |
| US3287411A (en) | Process of making aliphatic amines | |
| ES8103729A1 (en) | Benzimidazole derivatives, their use, and compositions containing these derivatives | |
| US3497555A (en) | Process of making aliphatic amines | |
| ES463971A1 (en) | IMPROVEMENTS IN OR RELATED TO ORGANIC COMPOUNDS. | |
| MX3394E (en) | PROCEDURE FOR PREPARING BENZOPHENONES | |
| ES470916A1 (en) | 4-Hydroxy-2-quinolinone-3-carboxylic acids, their preparation and pharmaceutical compositions containing them. | |
| ES8304978A1 (en) | Tryptamine derivatives of thienyloxypropanol amines, process for their preparation, pharmaceutical compositions containing them and preparation of the latter. | |
| GB1377352A (en) | 2-trifluoromethylimino derivatives of heterocyclic compounds with five-membered rings a process for their production and their use as fungicides insecticides or acaricides | |
| ES8602002A1 (en) | 4-Phenyl-tetrahydro-furano-pyridines, process for their preparation and pharmaceutical compositions. | |
| ES8301919A1 (en) | PROCEDURE FOR PREPARING DERIVATIVES OF INDANO | |
| ES8303333A1 (en) | PROCEDURE FOR PREPARING DERIVATIVES OF INDOL OR INDOLINA. | |
| JPS5289640A (en) | Guanidinobenzoic acid derivatives, and antiplasmin agents and remedies for pancreas diseases containing the said guanidinobensolc acid deriv atives | |
| ES8301957A1 (en) | Heterocyclic compounds, medicaments containing them and process for the preparation of these heterocyclic compounds and medicaments. | |
| ES8800181A1 (en) | Isocyanate compounds and their production. | |
| US3832378A (en) | Alpha-(chlorothio)isobutyronitrile,alpha-(chlorodithio)isobutyronitrile and their preparation;and preparation of alpha,alpha'-dithiobisisobutyronitrile |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FD1A | Patent lapsed |
Effective date: 19971001 |