SU520911A3 - Способ получени цианфенилкарбонатов - Google Patents
Способ получени цианфенилкарбонатовInfo
- Publication number
- SU520911A3 SU520911A3 SU1961001A SU1961001A SU520911A3 SU 520911 A3 SU520911 A3 SU 520911A3 SU 1961001 A SU1961001 A SU 1961001A SU 1961001 A SU1961001 A SU 1961001A SU 520911 A3 SU520911 A3 SU 520911A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- general formula
- producing
- cyanophenyl
- carbonates
- base
- Prior art date
Links
- JUUJGJKBAHKKSW-UHFFFAOYSA-N (2-cyanophenyl) hydrogen carbonate Chemical class OC(=O)OC1=CC=CC=C1C#N JUUJGJKBAHKKSW-UHFFFAOYSA-N 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 2
- -1 S cycloaliphatic Chemical group 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 150000002923 oximes Chemical class 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LSURXQXLLYDSFZ-UHFFFAOYSA-N (4-cyano-2,6-diiodophenyl) carbonochloridate Chemical compound IC1=C(C(=CC(=C1)C#N)I)OC(=O)Cl LSURXQXLLYDSFZ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
- C07C249/12—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reactions not involving the formation of oxyimino groups
-
- 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
- A01N47/02—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 no bond to a nitrogen atom
- A01N47/06—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 no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/62—Oximes having oxygen atoms of oxyimino groups esterified
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/62—Oximes having oxygen atoms of oxyimino groups esterified
- C07C251/64—Oximes having oxygen atoms of oxyimino groups esterified by carboxylic acids
- C07C251/68—Oximes having oxygen atoms of oxyimino groups esterified by carboxylic acids with at least one of the esterifying carboxyl groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
(54) СПОСОБ ПОЛУЧЕНИЯ ЦИАНФЕНИЛКАРБОНАТОВ
зил, фенилэтил, замещенный на низший алкил , например метил, этил, на галоген, например хлор или бром, или на низший алкоксил , например метоксил или этоксил.
Полученные цианфенилкарбонаты эффективны при борьбе с сх)рн ками тюю проса в посевах риса и злаковых культур. Они не фитотоксичны дл культурных растений.
Форма применени гербицидных препаратов обычна : дусты, гранулы, растворы, эмульсии или суспензии с добавкой жидких и/или твердых носителей или разбавителей, смачивателей , адгезивов. эмульгаторов и/или диспергаторов .
Пример. JL35,6 г (0,366 моль) 3,5-дийо -4-оксибензонитрила суспендируют в растворе, содержащем 26 мл фосгена в 5ОО мл уксусного эфира, при размешивании и О - 5 С добавл ют по капл м раствор, содержащий 46,5 мл N, N-диметиланилида в 50О мл уксусного эфира, нагревают 15 мин до 45 С, перемешивают при этой температуре ЗО мин, охлаждают до комнарной температуры, фильтруют, выливают фильтрат на лед, при О С промьшают органичеокую фазу разбавленной сол ной кис;1сгой и водой, сушат сульфатом магни , упаривают в вакууме, перекристаллизовьшают остаток из 5ОО мл пентана и получают 122,7 г (78%) 2,6-дийод-4-цианфениловохх) эфира хлормуравьиной кислоты, т. пл. 154-157 С.
Раствор 17,8 г 2,6-дийод-4-цианфенилового эфира хлормуравьиной кислоты в 5О мл ТГФ приливают по капл м при перемешивании и 18-2О С в раствор, содержащий 3,48 г (0,О4 моль) метилэтилкетоксима и 5,6 мл триэтиламива в 5 О мл ТГФ, перемешивают 3 час при комнатной температуре, выливают на лед, при О С промывают органическую фазу разбавленным раствором едкого натра и водой, сушат сульфатом магни , упаривают в вакууме, перекристаллизовываюг остаток из пентана и получают 15,0 г (77%) 1-этилэтилиденамино- (2,6-дийо/Ь4-циа№фенил )-карбоиата, т. пл. 107-1О8 С (разл.).
В таблиде приведены соединени , полученные аналогичным образом.
s с ю
ф
S
ж
ч
И
ю
S
о
а
а
ID
0)
s
ч о
§
о.
с
15, ,
Claims (1)
- Формула изобре н иСпособ получени цианфенилкарбона-гов обшей формулыBl(J ir-o-(io-o/Егде 5 и 1, - одинаковые или различные моно- или полизамещенные алифатические, Ю циклоалифатические, ароматические или арилалифатические углеводородные радикалы, или R - водород;X и У - одинаковые или различные галогены , отличающийс тем, что 15 галогензамещенный оксибензонитрил общей формулыСиНОгде X и У имеют выщеуказанные значени ,16подвергаюг взаимодействию с фосгеном при О-5 С в присутствии основани с дальнейщей обработкой образовавшегос эфира хлирмуравьиной кислогы общей формулыCi-CO-0где X и У - как указано вьше, обрабатьшают оксимом общей формулыКК; j if-oH/кгде R и Rj имеют указанные выше значени , в среде органического расгворител в присутствии основани с последующим выделением целевого продукта.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2210540A DE2210540C2 (de) | 1972-03-02 | 1972-03-02 | Cyanphenylcarbonate, Verfahren zu deren Herstellung sowie diese enthaltende herbizide Mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU520911A3 true SU520911A3 (ru) | 1976-07-05 |
Family
ID=5837941
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1890214A SU503483A3 (ru) | 1972-03-02 | 1973-03-02 | Гербицидна смесь |
| SU1961001A SU520911A3 (ru) | 1972-03-02 | 1973-09-10 | Способ получени цианфенилкарбонатов |
| SU731961001D SU520921A3 (ru) | 1972-03-02 | 1973-09-10 | Вулканизуема резинова смесь |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1890214A SU503483A3 (ru) | 1972-03-02 | 1973-03-02 | Гербицидна смесь |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU731961001D SU520921A3 (ru) | 1972-03-02 | 1973-09-10 | Вулканизуема резинова смесь |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US3895046A (ru) |
| JP (1) | JPS535733B2 (ru) |
| KR (1) | KR790000143B1 (ru) |
| AT (1) | AT321640B (ru) |
| AU (1) | AU470414B2 (ru) |
| BE (1) | BE796222A (ru) |
| CA (1) | CA993880A (ru) |
| CH (1) | CH588809A5 (ru) |
| CS (1) | CS168628B2 (ru) |
| DD (1) | DD107380A5 (ru) |
| DE (1) | DE2210540C2 (ru) |
| DK (1) | DK136419C (ru) |
| ES (1) | ES411617A1 (ru) |
| FI (1) | FI57099C (ru) |
| FR (1) | FR2174232B1 (ru) |
| GB (1) | GB1435351A (ru) |
| HU (1) | HU168566B (ru) |
| IL (1) | IL41663A (ru) |
| IT (1) | IT981071B (ru) |
| LU (1) | LU67127A1 (ru) |
| NL (1) | NL7302943A (ru) |
| PL (1) | PL91658B1 (ru) |
| RO (3) | RO62615A2 (ru) |
| SE (1) | SE396948B (ru) |
| SU (3) | SU503483A3 (ru) |
| TR (1) | TR18355A (ru) |
| ZA (1) | ZA731481B (ru) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1516404A (en) * | 1975-04-22 | 1978-07-05 | Fujisawa Pharmaceutical Co | Carbonic acid esters and the preparation thereof |
| US3957990A (en) * | 1975-03-05 | 1976-05-18 | Morton-Norwich Products, Inc. | Oxime carbamates |
| US4014915A (en) * | 1975-04-22 | 1977-03-29 | Fujisawa Pharmaceutical Co., Ltd. | Oxime carbonates |
| US4353735A (en) * | 1978-08-31 | 1982-10-12 | Ciba-Geigy Corporation | Oxime derivatives for protecting plant crops |
| US4488898A (en) * | 1978-08-31 | 1984-12-18 | Ciba-Geigy Corporation | Oxime derivatives for protecting plant crops |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT287683B (de) * | 1968-04-17 | 1971-02-10 | Boehringer Sohn Ingelheim | Verfahren zur Herstellung von neuen Kohlensäuremischestern |
| DE1809385A1 (de) * | 1968-11-16 | 1970-06-11 | Bayer Ag | Oxim-O-kohlensaeure-phenylester sowie Verfahren zu ihrer Herstellung |
-
1972
- 1972-03-02 DE DE2210540A patent/DE2210540C2/de not_active Expired
-
1973
- 1973-01-24 TR TR18355A patent/TR18355A/xx unknown
- 1973-02-06 CH CH169373A patent/CH588809A5/xx not_active IP Right Cessation
- 1973-02-08 DK DK68873A patent/DK136419C/da active
- 1973-02-13 CS CS1049A patent/CS168628B2/cs unknown
- 1973-02-14 ES ES411617A patent/ES411617A1/es not_active Expired
- 1973-02-19 DD DD168928A patent/DD107380A5/xx unknown
- 1973-02-23 FI FI558/73A patent/FI57099C/fi active
- 1973-02-26 GB GB933973A patent/GB1435351A/en not_active Expired
- 1973-02-26 US US335662A patent/US3895046A/en not_active Expired - Lifetime
- 1973-02-26 AU AU52604/73A patent/AU470414B2/en not_active Expired
- 1973-02-26 AT AT169173A patent/AT321640B/de not_active IP Right Cessation
- 1973-02-28 LU LU67127A patent/LU67127A1/xx unknown
- 1973-02-28 KR KR7300330A patent/KR790000143B1/ko not_active Expired
- 1973-03-01 HU HUSC426A patent/HU168566B/hu unknown
- 1973-03-01 RO RO74036A patent/RO62615A2/ro unknown
- 1973-03-01 RO RO7383545A patent/RO68498A/ro unknown
- 1973-03-01 SE SE7302902A patent/SE396948B/xx unknown
- 1973-03-01 RO RO7383546A patent/RO68499A/ro unknown
- 1973-03-01 FR FR7307317A patent/FR2174232B1/fr not_active Expired
- 1973-03-02 PL PL1973161032A patent/PL91658B1/pl unknown
- 1973-03-02 IL IL41663A patent/IL41663A/xx unknown
- 1973-03-02 CA CA165,132A patent/CA993880A/en not_active Expired
- 1973-03-02 SU SU1890214A patent/SU503483A3/ru active
- 1973-03-02 ZA ZA731481A patent/ZA731481B/xx unknown
- 1973-03-02 IT IT21127/73A patent/IT981071B/it active
- 1973-03-02 BE BE128327A patent/BE796222A/xx unknown
- 1973-03-02 NL NL7302943A patent/NL7302943A/xx not_active Application Discontinuation
- 1973-03-02 JP JP2500273A patent/JPS535733B2/ja not_active Expired
- 1973-09-10 SU SU1961001A patent/SU520911A3/ru active
- 1973-09-10 SU SU731961001D patent/SU520921A3/ru active
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