HU184202B - Selective herbicide composition containing 3-/methoxy-carbonyl-mino/-phenyl ester of n-ethyl-carbamidic acid and process for preparing 3-/methoxy-carbonyl-amino/-phenyl ester of n-ethyl-n-phenyl-carbamidic acid - Google Patents
Selective herbicide composition containing 3-/methoxy-carbonyl-mino/-phenyl ester of n-ethyl-carbamidic acid and process for preparing 3-/methoxy-carbonyl-amino/-phenyl ester of n-ethyl-n-phenyl-carbamidic acid Download PDFInfo
- Publication number
- HU184202B HU184202B HU79SCHE677A HUSC000677A HU184202B HU 184202 B HU184202 B HU 184202B HU 79SCHE677 A HU79SCHE677 A HU 79SCHE677A HU SC000677 A HUSC000677 A HU SC000677A HU 184202 B HU184202 B HU 184202B
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- HU
- Hungary
- Prior art keywords
- ethyl
- carbonyl
- methoxy
- phenyl
- phenyl ester
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- 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
- A01N47/22—O-Aryl or S-Aryl esters thereof
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- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
A találmány tárgya új eljárás az N-etil-N-fenil-karbamidsav-[3-(metoxi-karbonil-amino)-fenil]-észter előállítására.The present invention relates to a novel process for the preparation of N-ethyl-N-phenylcarbamic acid [3- (methoxycarbonylamino) phenyl] ester.
Szelektív herbicid hatású fenil-karbamidsav-származékokat tartalmazó szerek már ismertek (1 567 151 sz. 5 német szövetségi köztársaságbeli szabadalmi leírás).Agents containing phenylcarbamic acid derivatives having a selective herbicidal action are already known (German Patent No. 1,567,151).
A fenil-karbamidsav-származékokat klór-hangyasav-3(metoxi-karbonil-amino)-fenilészterek aminokkal való reagáltatásával (164 323 számú magyar szabadalmi leírás) vagy N-hidroxi-fenil-karbamidsavészterek megfelelően helyettesített karbamidsav-kloridokkal való reagáltatásával (154 047 számú magyar szabadalmi leírás) állítják elő.Phenylcarbamic acid derivatives are reacted with chloroformic acid 3- (methoxycarbonylamino) phenyl esters with amines (U.S. Patent No. 164,323) or by reacting N-hydroxyphenylcarbamic acid esters with appropriately substituted carbamic acid chlorides (No. 154,047). Hungarian Patent Specification).
A találmány feladata új eljárás kidolgozása az (I) képletű N-etil-N-fenil-karbamidsav- [3-(metoxi-karbonilamino)-fenil]-észter előállítására. Ez a vegyület szelektív herbicid szerek hatóanyagaként alkalmazható.It is an object of the present invention to provide a novel process for the preparation of N-ethyl-N-phenylcarbamic acid [3- (methoxycarbonylamino) phenyl] ester of formula (I). This compound is useful as an active ingredient in selective herbicides.
A találmány értelmében úgy járunk el, hogy (II) képletű N-etil-N-fenil-karbamidsav-3-nitro-fenil-észtert katalitikusán - például nikkel alkalmazásával metanolban — a megfelelő aminná hidrogénezünk, majd valamely savakceptor - például egy szervetlen bázis, így nátriumhidroxid, nátrium-karbonát vagy kálium-karbonát, vagy egy tercier szerves bázis, így például trietil-amin — jelenlétében (III) képletű klór-hangyasav-metil-észterrel reagáltatjuk és a kapott terméket a szokásos módon elkülönítjük.According to the invention, the N-ethyl-N-phenylcarbamic acid 3-nitrophenyl ester of formula (II) is catalytically hydrogenated, for example using nickel in methanol, to the corresponding amine, followed by an acid acceptor such as an inorganic base Thus, in the presence of sodium hydroxide, sodium carbonate or potassium carbonate or a tertiary organic base such as triethylamine, the methyl ester of chloroformate (III) is isolated and the product is isolated in the usual manner.
A találmányt az alábbi példával szemléltetjük:The invention is illustrated by the following example:
PéldaExample
a) 46,0 g (0,16 mól) N-etil-N-fenil-karbamidsav-(3nitro-fenil)-észtert 400 ml tetrahidrofuránban 5 g Raneynikkellel 20-25 °C-on hidrogénezünk. A Raney-nikkel leszűrése után az oldatot csökkentett nyomáson bepároljuk, és a maradékot etil-acetát és pentán elegyéből átkristályosítjuk.a) N-Ethyl-N-phenylcarbamic acid (3-nitrophenyl) ester (46.0 g, 0.16 mol) was hydrogenated in 400 ml of tetrahydrofuran with 5 g of Raneynickel at 20-25 ° C. After filtration of Raney nickel, the solution was concentrated under reduced pressure and the residue was recrystallized from ethyl acetate / pentane.
Kitermelés: 25,4 g N-etü-N-fenü-karbamidsav-(3-amino-fenil)-észter (az elméleti érték 62 %-a).Yield: 25.4 g of N-ethyl-N-phenylcarbamic acid (3-aminophenyl) ester (62% of theory).
Olvadáspont: 68-70 °C.Melting point: 68-70 ° C.
b) 25 g (0,0975 mól) N-etil-N-fenil-karbamidsav-(3amino-fenil)-észtert kevés etil-acetátban feloldunk. 20 ml víz és 4,0 g (0,1 mól) magnézium-oxid hozzáadása után 10 keverés, valamint 10-15 °C-ra való hűtés közben 9,2 g (0,0975 mól) klór-hangyasav-metil-észtert csepegtetünk hozzá. Az elegyet 30 percig 15 °C-on tovább keverjük, majd a szerves fázist elkülönítjük, híg sósav-oldattal és vízzel mossuk, és magnézium-szulfáttal végzett szárítás 15 után csökkentett nyomáson bepároljuk. Az olajos maradékot izopropil-éter és pentán elegyéből kristályosítjuk. Kitermelés: 27,9 g N-etil-N-fenil-karbamidsav-[3-(met· oxi-karbonil-amino-fenil)-észter (az elméleti értéke 91 %-a).b) 25 g (0.0975 moles) of N-ethyl-N-phenylcarbamic acid (3-aminophenyl) ester are dissolved in a little ethyl acetate. After the addition of 20 ml of water and 4.0 g (0.1 mol) of magnesium oxide, 9.2 g (0.0975 mol) of methyl chloroformate were added with stirring and cooling to 10-15 ° C. drip it. After further stirring at 15 ° C for 30 minutes, the organic phase was separated, washed with dilute hydrochloric acid and water and, after drying over magnesium sulfate, concentrated under reduced pressure. The oily residue was crystallized from a mixture of isopropyl ether and pentane. Yield: 27.9 g of N-ethyl-N-phenylcarbamic acid 3- (methoxycarbonylaminophenyl) ester (91% of theory).
Olvadáspont: 110-110,5 °C.Melting point: 110-110.5 ° C.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2819748A DE2819748C2 (en) | 1978-05-02 | 1978-05-02 | N-Ethylcarbanilic acid (3-methoxycarbonylamino) phenyl ester, a process for the preparation of this compound and a selective herbicidal agent containing it |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU184202B true HU184202B (en) | 1984-07-30 |
Family
ID=6038754
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU79SCHE677A HU184202B (en) | 1978-05-02 | 1979-04-27 | Selective herbicide composition containing 3-/methoxy-carbonyl-mino/-phenyl ester of n-ethyl-carbamidic acid and process for preparing 3-/methoxy-carbonyl-amino/-phenyl ester of n-ethyl-n-phenyl-carbamidic acid |
Country Status (31)
| Country | Link |
|---|---|
| JP (1) | JPS54144338A (en) |
| AR (1) | AR222653A1 (en) |
| AT (1) | AT365895B (en) |
| AU (1) | AU522366B2 (en) |
| BE (1) | BE875991A (en) |
| BR (1) | BR7902627A (en) |
| CA (1) | CA1108639A (en) |
| CH (1) | CH639946A5 (en) |
| CS (1) | CS207787B2 (en) |
| DD (1) | DD143200A5 (en) |
| DE (1) | DE2819748C2 (en) |
| EG (1) | EG13834A (en) |
| ES (1) | ES478923A1 (en) |
| FI (1) | FI790909A (en) |
| FR (1) | FR2424905A1 (en) |
| GB (1) | GB2020283B (en) |
| GR (1) | GR73571B (en) |
| HU (1) | HU184202B (en) |
| IL (1) | IL57073A (en) |
| IN (1) | IN150828B (en) |
| IT (1) | IT1166730B (en) |
| MX (1) | MX5787E (en) |
| NL (1) | NL7901680A (en) |
| PH (1) | PH14259A (en) |
| PL (1) | PL116642B1 (en) |
| PT (1) | PT69398A (en) |
| RO (3) | RO78022A (en) |
| SE (1) | SE7902441L (en) |
| SU (1) | SU852167A3 (en) |
| TR (1) | TR20603A (en) |
| YU (1) | YU40364B (en) |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1567151C3 (en) * | 1965-04-09 | 1974-02-21 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | Diurethanes, processes for the preparation of these compounds and herbicidal compositions containing them |
| US3535101A (en) * | 1966-09-07 | 1970-10-20 | Schering Ag | Herbicide and algicide means |
| US3901936A (en) * | 1966-10-15 | 1975-08-26 | Schering Ag | Process for the preparation of n-carbamoyloxyphenyl carbamates |
| JPS5140073A (en) * | 1974-06-28 | 1976-04-03 | Siemens Ag | SHIRIKONNODOOPINGUHOHO |
| DE2557552C2 (en) * | 1975-12-18 | 1984-12-20 | Schering AG, 1000 Berlin und 4709 Bergkamen | Diurethanes and herbicidal agents containing these compounds as active ingredients |
-
1978
- 1978-05-02 DE DE2819748A patent/DE2819748C2/en not_active Expired
-
1979
- 1979-03-02 NL NL7901680A patent/NL7901680A/en not_active Application Discontinuation
- 1979-03-16 FI FI790909A patent/FI790909A/en not_active Application Discontinuation
- 1979-03-19 SE SE7902441A patent/SE7902441L/en unknown
- 1979-03-19 YU YU667/79A patent/YU40364B/en unknown
- 1979-03-23 ES ES478923A patent/ES478923A1/en not_active Expired
- 1979-03-27 PT PT69398A patent/PT69398A/en unknown
- 1979-03-29 IN IN208/DEL/79A patent/IN150828B/en unknown
- 1979-04-06 IT IT21636/79A patent/IT1166730B/en active
- 1979-04-07 GR GR58833A patent/GR73571B/el unknown
- 1979-04-15 IL IL7957073A patent/IL57073A/en unknown
- 1979-04-18 AR AR276229A patent/AR222653A1/en active
- 1979-04-20 CS CS792753A patent/CS207787B2/en unknown
- 1979-04-23 GB GB7914092A patent/GB2020283B/en not_active Expired
- 1979-04-25 CA CA326,275A patent/CA1108639A/en not_active Expired
- 1979-04-25 DD DD79212488A patent/DD143200A5/en unknown
- 1979-04-26 MX MX797937U patent/MX5787E/en unknown
- 1979-04-27 HU HU79SCHE677A patent/HU184202B/en unknown
- 1979-04-27 SU SU792757223A patent/SU852167A3/en active
- 1979-04-30 TR TR20603A patent/TR20603A/en unknown
- 1979-04-30 CH CH405879A patent/CH639946A5/en not_active IP Right Cessation
- 1979-04-30 BR BR7902627A patent/BR7902627A/en unknown
- 1979-04-30 RO RO7987405A patent/RO78022A/en unknown
- 1979-04-30 RO RO79104234A patent/RO80177A/en unknown
- 1979-04-30 PH PH22442A patent/PH14259A/en unknown
- 1979-04-30 AT AT0323279A patent/AT365895B/en not_active IP Right Cessation
- 1979-04-30 PL PL1979215274A patent/PL116642B1/en unknown
- 1979-05-01 AU AU46578/79A patent/AU522366B2/en not_active Ceased
- 1979-05-01 JP JP5256679A patent/JPS54144338A/en active Pending
- 1979-05-02 FR FR7911009A patent/FR2424905A1/en active Granted
- 1979-05-02 BE BE0/194952A patent/BE875991A/en not_active IP Right Cessation
- 1979-05-02 EG EG254/79A patent/EG13834A/en active
- 1979-05-30 RO RO79104223A patent/RO80176A/en unknown
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