RO94658B - Procedeu de preparare a unui derivat de n-(3-clor-4-izopropil-fenil)-carboxamida - Google Patents
Procedeu de preparare a unui derivat de n-(3-clor-4-izopropil-fenil)-carboxamidaInfo
- Publication number
- RO94658B RO94658B RO123442A RO12344286A RO94658B RO 94658 B RO94658 B RO 94658B RO 123442 A RO123442 A RO 123442A RO 12344286 A RO12344286 A RO 12344286A RO 94658 B RO94658 B RO 94658B
- Authority
- RO
- Romania
- Prior art keywords
- chloro
- reaction
- preparation
- hydroxide
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title abstract 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 abstract 1
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 abstract 1
- RROSMHZQLKYMGM-UHFFFAOYSA-N 3-chloro-4-propan-2-ylaniline Chemical compound CC(C)C1=CC=C(N)C=C1Cl RROSMHZQLKYMGM-UHFFFAOYSA-N 0.000 abstract 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 abstract 1
- 229940117389 dichlorobenzene Drugs 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 230000002363 herbicidal effect Effects 0.000 abstract 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- SIAITKXDBJNXPH-UHFFFAOYSA-N n-(3-chloro-4-propan-2-ylphenyl)formamide Chemical class CC(C)C1=CC=C(NC=O)C=C1Cl SIAITKXDBJNXPH-UHFFFAOYSA-N 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 abstract 1
- 235000017557 sodium bicarbonate Nutrition 0.000 abstract 1
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract 1
- JBJWASZNUJCEKT-UHFFFAOYSA-M sodium;hydroxide;hydrate Chemical compound O.[OH-].[Na+] JBJWASZNUJCEKT-UHFFFAOYSA-M 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- 239000008096 xylene Substances 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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
-
- 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)
- 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
Inventia se refera la un procedeu de preparare a unui derivat de N-(3-clor-4-izopropilfenil)-carboxamida, cu actiune erbicida selectiva, cu formula generala I (vezi formula în pag.1 a descrierii) în care R reprezinta o grupa 1-metilbutil, 1-metilciclopropil sau ciclopropil, prin tratarea 3-clor-4-izopropilianilinei cu un derivat de acid carboxilic cu formula generala II 8vezi formula în pag.1 a descrierii) în care R are semnificatiile de la formula I, iar X reprezinta halogen, atunci cînd n=1, si oxigen, atunci cînd n=2, reactia avînd loc într-un solvent inert ales dintre benzen, toluen, xilen, clorbenzen, diclorbenzen, acetona, metiletilcetona, acetonitril, propionitril, eter etilic, tetrahidrofuran, dioxan, dimetilformamida, dimetilsulfoxid si hexametilfosforamida, în prezenta unui agent de neutralizare a acidului rezultat din reactie, ales dintre trietilamina, piridina, dimetilanilina, 1,8-diazabiciclo-(5,4,0)-7-undecena, carbonat de potasiu, carbonat de sodiu, hidroxid de sodiu, hidroxid de potasiu si bicarbonat de sodiu, la temperaturi cuprinse între 0 degree C si temperatura de reflux a amestecului de reactie.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11208785 | 1985-05-27 | ||
| JP11659185A JPH064575B2 (ja) | 1985-05-31 | 1985-05-31 | N−(3−クロロ−4−イソプロピルフエニル)シクロプロパンカルボン酸アミド誘導体および選択性殺草剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RO94658A RO94658A (ro) | 1988-06-30 |
| RO94658B true RO94658B (ro) | 1988-07-01 |
Family
ID=26451325
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RO123442A RO94658B (ro) | 1985-05-27 | 1986-05-26 | Procedeu de preparare a unui derivat de n-(3-clor-4-izopropil-fenil)-carboxamida |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4749812A (ro) |
| EP (1) | EP0205271B1 (ro) |
| AU (1) | AU594342B2 (ro) |
| DE (1) | DE3661997D1 (ro) |
| HU (1) | HU198008B (ro) |
| NZ (1) | NZ216253A (ro) |
| RO (1) | RO94658B (ro) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4716175A (en) * | 1987-02-24 | 1987-12-29 | Warner-Lambert Company | Saturated fatty acid amides as inhibitors of acyl-CoA:cholesterol acyltransferase |
| DE3814505A1 (de) * | 1988-04-29 | 1989-11-09 | Bayer Ag | Substituierte cycloalkyl- bzw. heterocyclyl-carbonsaeureanilide |
| US5461027A (en) * | 1989-01-24 | 1995-10-24 | Griffin Corporation | Microencapsulated pendimethalin and method of making and using same |
| US5270154A (en) * | 1992-01-31 | 1993-12-14 | Fuji Hunt Photographic Chemicals Inc. | Method of making flowable alkaline thiosulfate/alkaline sulfite and the product thereof |
| EP2052606A1 (de) | 2007-10-24 | 2009-04-29 | Bayer CropScience AG | Herbizid-Kombination |
| DE102008037620A1 (de) | 2008-08-14 | 2010-02-18 | Bayer Crop Science Ag | Herbizid-Kombination mit Dimethoxytriazinyl-substituierten Difluormethansulfonylaniliden |
| HUE034803T2 (en) | 2010-10-15 | 2018-02-28 | Bayer Ip Gmbh | Use of ALS inhibitor herbicides to control undesirable vegetation in ALS inhibitor herbicide-tolerant beta vulgaris plants |
| EA029716B1 (ru) | 2011-05-04 | 2018-05-31 | Байер Интеллектчуал Проперти Гмбх | Применение гербицидов ингибиторов als для борьбы с нежелательными растениями среди растений brassica, таких как b. napus, толерантных к гербицидам ингибиторов als |
| RS57806B2 (sr) | 2012-12-13 | 2022-07-29 | Bayer Cropscience Ag | Upotreba als inhibitora herbicida za kontrolu neželjene vegetacije kod beta vulgaris biljaka tolerantnih na als inhibitore herbicida |
| AR127377A1 (es) | 2021-10-15 | 2024-01-17 | Kws Saat Se & Co Kgaa | Mutantes de beta vulgaris tolerantes a herbicidas inhibidores de als |
Family Cites Families (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2655445A (en) * | 1949-12-06 | 1953-10-13 | Du Pont | 3-(halophenyl)-1-methyl-1-(methyl or ethyl) ureas and herbicidal compositions and methods employing same |
| US2655444A (en) * | 1952-02-14 | 1953-10-13 | Du Pont | 3-(halophenyl)-1, 1-dialkyl ureas and weed control compositions and methods |
| NL95401C (ro) * | 1954-07-06 | |||
| GB793513A (en) * | 1954-09-09 | 1958-04-16 | May & Baker Ltd | Process for the preparation of ª†-4-chloro-2-methylphenoxybutyric acid and derivatives thereof |
| US2756135A (en) * | 1955-07-13 | 1956-07-24 | Du Pont | 1-methyl-3-(2-benzothiazolyl)-ureas and their use as herbicides |
| US2960534A (en) * | 1957-06-11 | 1960-11-15 | Hoechst Ag | Nu-(chlorosubstituted aryl)-nu' methoxy-nu' methyl ureas |
| US3816092A (en) * | 1958-02-13 | 1974-06-11 | Rohm & Haas | Herbicidal 3,1-dichloroanilides |
| DK100668A (ro) * | 1958-03-24 | |||
| NL120013C (ro) * | 1958-04-14 | |||
| US3249633A (en) * | 1958-07-23 | 1966-05-03 | Union Carbide Corp | Acrylic acid ester synthesis |
| US3277107A (en) * | 1962-03-16 | 1966-10-04 | Gulf Oil Corp | Cyclopropanecarboxamide and cyclopropanethiocarboxamide derivatives |
| NL291363A (ro) * | 1962-04-10 | |||
| US3201466A (en) * | 1963-03-08 | 1965-08-17 | Gulf Oil Corp | Substituted cyclopropanecarboxanilide herbicides |
| NL123536C (ro) * | 1963-07-09 | |||
| DE1189312B (de) * | 1963-12-06 | 1965-03-18 | Schering Ag | Mittel mit selektiver herbizider Wirkung |
| FR1497868A (fr) * | 1965-10-28 | 1967-10-13 | Sandoz Sa | Procédé de lutte sélective contre les plantes adventices dans les cultures de céréales |
| FR1497867A (fr) * | 1965-10-28 | 1967-10-13 | Sandoz Sa | Procédé de lutte sélective contre les plantes adventices dans les cultures de carottes |
| NL131196C (ro) * | 1966-07-16 | |||
| GB1164160A (en) * | 1966-12-30 | 1969-09-17 | Shell Int Research | N,N-Disubstituted Amino Acid Derivatives and their use as Herbicides |
| DE1913850A1 (de) * | 1969-03-19 | 1970-10-01 | Basf Ag | Herbizid |
| US3784635A (en) * | 1969-04-25 | 1974-01-08 | Mobil Oil Corp | Substituted phenoxybenzoic acids and esters thereof |
| IL36218A0 (en) * | 1970-02-27 | 1971-04-28 | Ciba Geigy Ag | 4-isopropylphenylureas,their manufacture and use in combating pests |
| FR2104706B1 (ro) * | 1970-08-06 | 1974-03-22 | Pepro | |
| CA985523A (en) * | 1971-06-30 | 1976-03-16 | American Cyanamid Company | Inhibiting plant bud growth |
| DE2223894C3 (de) * | 1972-05-17 | 1981-07-23 | Hoechst Ag, 6000 Frankfurt | Herbizide Mittel auf Basis von Phenoxycarbonsäurederivaten |
| DE2249547A1 (de) * | 1972-10-10 | 1974-04-18 | Bayer Ag | Carbonsaeure-(3-halogen-4-alkyl-anilide), verfahren zu ihrer herstellung sowie ihre verwendung als herbizide |
| ZA744908B (en) * | 1973-09-17 | 1975-08-27 | American Cyanamid Co | Catalytic dehydrogenation process for the preparation of 3,5-disubstituted pyrazoles |
| OA05625A (fr) * | 1976-04-07 | 1981-04-30 | Du Pont | N-(hétérocyclique aminocarbonyl) aryl sulfonamides herbicides, compositions les contenant et procédés les utilisant . |
| CA1087186A (en) * | 1977-01-21 | 1980-10-07 | Kurt H. G. Pilgram | Cycloalkane-carboxanilides |
| US4166735A (en) * | 1977-01-21 | 1979-09-04 | Shell Oil Company | Cycloalkanecarboxanilide derivative herbicides |
| JPS56135456A (en) * | 1980-03-27 | 1981-10-22 | Sumitomo Chem Co Ltd | Substituted phenylurea derivative, its preparation and herbicide containing the same as active constituent |
| JPS5781449A (en) * | 1980-11-10 | 1982-05-21 | Sumitomo Chem Co Ltd | Cyclopropanecarboxamide derivative, its preparation and herbicide containinig said derivative as active component |
| US4517387A (en) * | 1982-09-30 | 1985-05-14 | Mitsui Petrochemical Industries, Ltd. | Process for production of 2,2-bis(4-hydroxyphenyl) propane |
| JPS59193806A (ja) * | 1983-04-19 | 1984-11-02 | Mitsui Toatsu Chem Inc | 選択性殺草剤 |
| JPS6023357A (ja) * | 1983-07-19 | 1985-02-05 | Mitsui Toatsu Chem Inc | 2−メチル−4′−イソプロピル−2−ペンテノイルアニリドおよび選択性殺草剤 |
-
1986
- 1986-05-21 NZ NZ216253A patent/NZ216253A/xx unknown
- 1986-05-21 US US06/865,437 patent/US4749812A/en not_active Expired - Fee Related
- 1986-05-23 DE DE8686303956T patent/DE3661997D1/de not_active Expired
- 1986-05-23 EP EP86303956A patent/EP0205271B1/en not_active Expired
- 1986-05-23 HU HU862206A patent/HU198008B/hu not_active IP Right Cessation
- 1986-05-23 AU AU57877/86A patent/AU594342B2/en not_active Ceased
- 1986-05-26 RO RO123442A patent/RO94658B/ro unknown
Also Published As
| Publication number | Publication date |
|---|---|
| RO94658A (ro) | 1988-06-30 |
| NZ216253A (en) | 1989-07-27 |
| US4749812A (en) | 1988-06-07 |
| HU198008B (en) | 1989-07-28 |
| AU5787786A (en) | 1986-12-04 |
| DE3661997D1 (en) | 1989-03-09 |
| AU594342B2 (en) | 1990-03-08 |
| EP0205271B1 (en) | 1989-02-01 |
| HUT44003A (en) | 1988-01-28 |
| EP0205271A1 (en) | 1986-12-17 |
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