AT342616B - Verfahren zur herstellung von neuen substituierten carbamoylimidazolderivaten - Google Patents
Verfahren zur herstellung von neuen substituierten carbamoylimidazolderivatenInfo
- Publication number
- AT342616B AT342616B AT844574A AT844574A AT342616B AT 342616 B AT342616 B AT 342616B AT 844574 A AT844574 A AT 844574A AT 844574 A AT844574 A AT 844574A AT 342616 B AT342616 B AT 342616B
- Authority
- AT
- Austria
- Prior art keywords
- sep
- reacted
- isocyanate
- benzimidazole
- methyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 12
- NMIZONYLXCOHEF-UHFFFAOYSA-N 1h-imidazole-2-carboxamide Chemical class NC(=O)C1=NC=CN1 NMIZONYLXCOHEF-UHFFFAOYSA-N 0.000 title 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 5
- FFYTTYVSDVWNMY-UHFFFAOYSA-N 2-Methyl-5-nitroimidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1 FFYTTYVSDVWNMY-UHFFFAOYSA-N 0.000 claims 4
- ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 claims 3
- MFUVCHZWGSJKEQ-UHFFFAOYSA-N 3,4-dichlorphenylisocyanate Chemical compound ClC1=CC=C(N=C=O)C=C1Cl MFUVCHZWGSJKEQ-UHFFFAOYSA-N 0.000 claims 3
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 claims 3
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 claims 3
- -1 (4'-chlorophenyl) -carbamoyl- Chemical group 0.000 claims 2
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims 2
- LDZYRENCLPUXAX-UHFFFAOYSA-N 2-methyl-1h-benzimidazole Chemical compound C1=CC=C2NC(C)=NC2=C1 LDZYRENCLPUXAX-UHFFFAOYSA-N 0.000 claims 1
- IDSPMEZZVFVWEV-UHFFFAOYSA-N 2-methyl-n-phenylbenzimidazole-1-carboxamide Chemical compound CC1=NC2=CC=CC=C2N1C(=O)NC1=CC=CC=C1 IDSPMEZZVFVWEV-UHFFFAOYSA-N 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
- C07D233/91—Nitro radicals
- C07D233/92—Nitro radicals attached in position 4 or 5
-
- 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
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/08—Radicals containing only hydrogen and carbon atoms
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
<Desc/Clms Page number 1> EMI1.1 EMI1.2 EMI1.3 EMI1.4 EMI1.5 <Desc/Clms Page number 2> EMI2.1 <Desc/Clms Page number 3> EMI3.1 **WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
Claims (1)
- EMI3.2 <tb> <tb> furVerbindung <SEP> Schmelzpunkt <SEP> Ausbeute <tb> 1-Phenylcarbamoyl-2-methylbenzimidazol <SEP> 130 <SEP> - <SEP> 1320C <SEP> 85, <SEP> 2% <tb> 1- <SEP> (4'-Chlorphenyl)-carbamoyl- <tb> -2-methylbenzimidazol <SEP> 162-164 C <SEP> 90, <SEP> 5% <tb> 1- <SEP> (3',4'-Dichlorphenyl)- <tb> - <SEP> carbamoyl-2-methyl- <SEP> <tb> benzimidazol <SEP> 171-174 C <SEP> 91, <SEP> 8% <tb> l-Cyclohexylcarbamoyl-2- <tb> - <SEP> methylbenzimidazol <SEP> 127 <SEP> - <SEP> 1290C <SEP> 88, <SEP> 5% <tb> EMI3.3 <Desc/Clms Page number 4> EMI4.1 EMI4.2 EMI4.3 EMI4.4 :Siedepunkt des Lösungsmittels, gegebenenfalls in Gegenwart eines tertiären Amins, als Katalysator umsetzt.2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, dass man 2-Methylimidazol mit Cy- clohexylisocyanat umsetzt.3. Verfahren nach Anspruch 1, dadurch gekennzeiohnet, daBman2-MethyllmldazolmitPhe- nylisocyanatumsetzt. EMI4.5 4-Chlorphenylisocyanat umsetzt.5. Verfahren nach Anspruch 1, dad ur ch gekennzeichnet, dass man 2-Methylimidazol mit 3,4- - Dichlorphenylisocyanat umsetzt.6. Verfahren nach Anspruch 1, dadurch gekennzeichnet, dass man 2-Methyl-5-nitroimidazol mit Cyclohexylisocyanat umsetzt.7. Verfahren nach Anspruch 1, dadurch gekennzeichnet, dass man 2-Methyl-5-nitroimidazol mit Phenylisocyanat umsetzt.8. Verfahren nach Anspruch 1, dadurch gekennzeichnet, dass man 2-Methyl-5-nitroimidazol mit 4-Chlorphenylisocyanat umsetzt.9. Verfahren nach Anspruch 1, dadurch gekennzeichnet, dass man 2-Methyl-5-nitroimidazol mit 3, 4-Dichlorphenylisocyanat umsetzt.10. Verfahren nach Anspruch 1, dadurch gekennzeichnet, dass man Benzimidazol mit Cyclohexylisocyanat umsetzt.11. Verfahren nach Anspruch 1, dadurch gekennzeichnet, dass man Benzimida zol mit Phenylisocyanat umsetzt.12. Verfahren nach Anspruch 1, dadurch gekennzeichnet, dass man Benzimidazol mit 4-Chlorphenylisocyanat umsetzt.13. Verfahren nach Anspruch 1, dadurch gekennzeichnet, dass man Benzimidazol mit 3,4-Di- chlorphenylisocyanat umsetzt.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUNE489A HU164653B (de) | 1971-07-23 | 1971-07-23 | |
| AT580373A AT325889B (de) | 1973-07-02 | 1973-07-02 | Herbizides und fungizides mittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| ATA844574A ATA844574A (de) | 1977-08-15 |
| AT342616B true AT342616B (de) | 1978-04-10 |
Family
ID=25602516
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT844574A AT342616B (de) | 1971-07-23 | 1973-07-02 | Verfahren zur herstellung von neuen substituierten carbamoylimidazolderivaten |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT342616B (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0193307A3 (en) * | 1985-02-25 | 1987-02-04 | Imperial Chemical Industries Plc | Process for the extraction of metal values and novel metal extractants |
-
1973
- 1973-07-02 AT AT844574A patent/AT342616B/de not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0193307A3 (en) * | 1985-02-25 | 1987-02-04 | Imperial Chemical Industries Plc | Process for the extraction of metal values and novel metal extractants |
Also Published As
| Publication number | Publication date |
|---|---|
| ATA844574A (de) | 1977-08-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ELJ | Ceased due to non-payment of the annual fee |