DD239792A5 - Verfahren zur herstellung von substituierten und unsubstituierten 2-carbamoyl-nikotin- und 3-chinolincarbocyclischen saeuren - Google Patents
Verfahren zur herstellung von substituierten und unsubstituierten 2-carbamoyl-nikotin- und 3-chinolincarbocyclischen saeuren Download PDFInfo
- Publication number
- DD239792A5 DD239792A5 DD85283625A DD28362585A DD239792A5 DD 239792 A5 DD239792 A5 DD 239792A5 DD 85283625 A DD85283625 A DD 85283625A DD 28362585 A DD28362585 A DD 28362585A DD 239792 A5 DD239792 A5 DD 239792A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- alkyl
- acid
- alkoxy
- hydrogen
- halogen
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 20
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Chemical compound CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 title 1
- DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical class C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 claims abstract description 17
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 claims description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
- -1 C 1 -C 4 -AHCyItHiO Chemical group 0.000 claims description 17
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 15
- 150000003512 tertiary amines Chemical class 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 235000001968 nicotinic acid Nutrition 0.000 claims description 8
- 150000007524 organic acids Chemical class 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 229960003512 nicotinic acid Drugs 0.000 claims description 7
- 239000011664 nicotinic acid Substances 0.000 claims description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 125000005219 aminonitrile group Chemical group 0.000 claims description 5
- 150000008064 anhydrides Chemical class 0.000 claims description 5
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- GPHQHTOMRSGBNZ-UHFFFAOYSA-N pyridine-4-carbonitrile Chemical compound N#CC1=CC=NC=C1 GPHQHTOMRSGBNZ-UHFFFAOYSA-N 0.000 claims 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 12
- 230000000694 effects Effects 0.000 description 10
- 230000003197 catalytic effect Effects 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 7
- 230000002363 herbicidal effect Effects 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- DIABIDLZBNRSPR-UHFFFAOYSA-N 2-carbamoylpyridine-3-carboxylic acid Chemical compound NC(=O)C1=NC=CC=C1C(O)=O DIABIDLZBNRSPR-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 244000025254 Cannabis sativa Species 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- CAOHBROWLMCZRP-UHFFFAOYSA-N 2-amino-2,3-dimethylbutanenitrile Chemical compound CC(C)C(C)(N)C#N CAOHBROWLMCZRP-UHFFFAOYSA-N 0.000 description 2
- PBHUSRBVKLAGGU-UHFFFAOYSA-N 2-carbamoylquinoline-3-carboxylic acid Chemical class C1=CC=C2C=C(C(O)=O)C(C(=O)N)=NC2=C1 PBHUSRBVKLAGGU-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- 244000281762 Chenopodium ambrosioides Species 0.000 description 2
- 244000058871 Echinochloa crus-galli Species 0.000 description 2
- 241000508725 Elymus repens Species 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 229910004373 HOAc Inorganic materials 0.000 description 2
- 244000020551 Helianthus annuus Species 0.000 description 2
- 235000003222 Helianthus annuus Nutrition 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 241001506766 Xanthium Species 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- GJAWHXHKYYXBSV-UHFFFAOYSA-N quinolinic acid Chemical compound OC(=O)C1=CC=CN=C1C(O)=O GJAWHXHKYYXBSV-UHFFFAOYSA-N 0.000 description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 1
- CLQMBPJKHLGMQK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)nicotinic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC=CC=C1C(O)=O CLQMBPJKHLGMQK-UHFFFAOYSA-N 0.000 description 1
- JRYYVMDEUJQWRO-UHFFFAOYSA-N 2-methylnicotinamide Chemical compound CC1=NC=CC=C1C(N)=O JRYYVMDEUJQWRO-UHFFFAOYSA-N 0.000 description 1
- NMWDYLYNWRFEMR-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1.CC1=CC=CC=N1 NMWDYLYNWRFEMR-UHFFFAOYSA-N 0.000 description 1
- CEZISCZZZSXYSP-UHFFFAOYSA-N 4-methylpyridine;toluene Chemical compound CC1=CC=CC=C1.CC1=CC=NC=C1 CEZISCZZZSXYSP-UHFFFAOYSA-N 0.000 description 1
- 235000003129 Ambrosia artemisiifolia var elatior Nutrition 0.000 description 1
- 235000007320 Avena fatua Nutrition 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 241000217446 Calystegia sepium Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 235000000509 Chenopodium ambrosioides Nutrition 0.000 description 1
- 235000005490 Chenopodium botrys Nutrition 0.000 description 1
- 241000207892 Convolvulus Species 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 241000209219 Hordeum Species 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 244000286695 Melinis minutiflora var. inermis Species 0.000 description 1
- 241000209094 Oryza Species 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 235000005373 Uvularia sessilifolia Nutrition 0.000 description 1
- 235000002096 Vicia faba var. equina Nutrition 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000007244 Zea mays Nutrition 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 235000003484 annual ragweed Nutrition 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 235000006263 bur ragweed Nutrition 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 235000003488 common ragweed Nutrition 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 244000013123 dwarf bean Species 0.000 description 1
- 235000005489 dwarf bean Nutrition 0.000 description 1
- MCQOWYALZVKMAR-UHFFFAOYSA-N furo[3,4-b]pyridine-5,7-dione Chemical compound C1=CC=C2C(=O)OC(=O)C2=N1 MCQOWYALZVKMAR-UHFFFAOYSA-N 0.000 description 1
- NLVZUORLSQCGFQ-UHFFFAOYSA-N furo[3,4-b]quinoline-1,3-dione Chemical compound C1=CC=C2C=C3C(=O)OC(=O)C3=NC2=C1 NLVZUORLSQCGFQ-UHFFFAOYSA-N 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 230000001795 light effect Effects 0.000 description 1
- 230000036244 malformation Effects 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 150000002814 niacins Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- VPODXHOUBDCEHN-UHFFFAOYSA-N pyridine-3-carbonyl pyridine-3-carboxylate Chemical compound C=1C=CN=CC=1C(=O)OC(=O)C1=CC=CN=C1 VPODXHOUBDCEHN-UHFFFAOYSA-N 0.000 description 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical class C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 description 1
- 235000009736 ragweed Nutrition 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Quinoline Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/677,647 US4782157A (en) | 1984-12-03 | 1984-12-03 | Preparation of substituted and unsubstituted 2-carbamoyl nicotinic and 3-quinolinecarboxylic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD239792A5 true DD239792A5 (de) | 1986-10-08 |
Family
ID=24719581
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD85283625A DD239792A5 (de) | 1984-12-03 | 1985-12-03 | Verfahren zur herstellung von substituierten und unsubstituierten 2-carbamoyl-nikotin- und 3-chinolincarbocyclischen saeuren |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4782157A (da) |
| EP (1) | EP0184027B1 (da) |
| JP (1) | JPH0764818B2 (da) |
| KR (1) | KR930001408B1 (da) |
| AT (1) | ATE50247T1 (da) |
| AU (1) | AU576407B2 (da) |
| BR (1) | BR8506021A (da) |
| CA (1) | CA1332606C (da) |
| DD (1) | DD239792A5 (da) |
| DE (1) | DE3542739C2 (da) |
| DK (1) | DK163184C (da) |
| ES (1) | ES8701728A1 (da) |
| HU (1) | HU199421B (da) |
| IE (1) | IE58643B1 (da) |
| IL (1) | IL77092A (da) |
| ZA (1) | ZA859223B (da) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4709036A (en) * | 1985-06-13 | 1987-11-24 | American Cyanamid Company | Process for the preparation of herbicidal 2-(4,4-disubstituted-5-oxo-2-imidazolin-2-yl)benzoic, nicotinic and quinoline-3-carboxylic acids, esters and salts |
| JP2572139B2 (ja) * | 1990-01-25 | 1997-01-16 | 旭化成工業株式会社 | 磁気抵抗センサー |
| US5250694A (en) * | 1992-08-26 | 1993-10-05 | American Cyanamid Company | Process for the preparation of 2,3-pyridine-dicarboxylic acids from 3-(2-imidazolin-2-yl)picolinic acids |
| US6339158B1 (en) | 1999-05-03 | 2002-01-15 | American Cyanamid Co. | Process for the preparation of chiral nicotinic, quinolinic or benzoic acid imidazolinone herbicides |
| BRPI0921883A2 (pt) | 2008-11-13 | 2020-08-04 | Basf Se | composto, processos para preparar um composto e para a fabricação de um composto, e, uso de um composto |
| MX2011004938A (es) * | 2008-11-13 | 2011-06-06 | Basf Se | Proceso para fabricar bromuros de 3-piridilmetilamonio sustituido. |
| EP2358678B1 (en) | 2008-11-13 | 2015-01-14 | Basf Se | Process for manufacturing 5-chloromethyl-2,3-pyridine dicarboxylic acid anhydrides |
| EP2376472B1 (en) | 2008-12-09 | 2015-08-19 | Basf Se | Process for manufacturing 5-formyl-pyridine-2,3-dicarboxylic acid esters |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE441707C (de) * | 1924-12-28 | 1927-03-10 | Chemische Ind Ges | Verfahren zur Darstellung von gesaettigten und ungesaettigten Dialkylamiden der Pyridin-3-carbonsaeure |
| NL7714092A (nl) * | 1976-12-22 | 1978-06-26 | Monsanto Co | Werkwijze voor het bereiden van nieuwe ftalamine- en nicotinezuren. |
| JPS5724364A (en) * | 1980-06-02 | 1982-02-08 | American Cyanamid Co | 2-(2-imidazoline-2-yl)pyridines and quinolines, manufacture and intermediate and herbicidal use |
| US4638068A (en) * | 1981-04-09 | 1987-01-20 | American Cyanamid Company | 2-(2-imidazolin-2-yl)-pyridines and quinolines, process and intermediates for the preparation thereof, and use of said compounds as herbicidal agents |
| US4459409A (en) * | 1982-05-25 | 1984-07-10 | American Cyanamid Company | Process for the preparation of 2,3-quinolinedicarboxylic acids |
| US4460776A (en) * | 1982-05-25 | 1984-07-17 | American Cyanamid Company | Process for the preparation of 6-substituted-2,3-pyridinedicarboxylic acid diesters |
| DE3474020D1 (en) * | 1983-08-02 | 1988-10-20 | American Cyanamid Co | Imidazolidinones, and imidazolidinethiones, process for the preparation thereof, and use of said compounds as herbicidal agents |
| US4562257A (en) * | 1983-11-07 | 1985-12-31 | American Cyanamid Company | Preparation of substituted and unsubstituted 2-carbamoyl nicotinic and 3-quinolinecarboxylic acids |
| US4719303A (en) * | 1983-11-21 | 1988-01-12 | American Cyanamid Company | Preparation of substituted and unsubstituted 2-[(1-carbamoyl-1,2-dimethylpropyl)-carbamoyl]-3-quinolinecarboxylic, nicotinic and benzoic acids |
| EP0166907A3 (en) * | 1984-06-04 | 1988-09-14 | American Cyanamid Company | Herbicidal 2-(2-imidazolin-2-yl)-fluoroalkoxy-, alkenyloxy- and alkynyloxypyridines and quinolines |
-
1984
- 1984-12-03 US US06/677,647 patent/US4782157A/en not_active Expired - Lifetime
-
1985
- 1985-11-11 AT AT85114305T patent/ATE50247T1/de not_active IP Right Cessation
- 1985-11-11 EP EP85114305A patent/EP0184027B1/en not_active Expired - Lifetime
- 1985-11-18 IL IL77092A patent/IL77092A/xx not_active IP Right Cessation
- 1985-11-29 CA CA000496512A patent/CA1332606C/en not_active Expired - Lifetime
- 1985-12-02 BR BR8506021A patent/BR8506021A/pt not_active IP Right Cessation
- 1985-12-02 AU AU50553/85A patent/AU576407B2/en not_active Expired
- 1985-12-02 ZA ZA859223A patent/ZA859223B/xx unknown
- 1985-12-02 IE IE301985A patent/IE58643B1/en not_active IP Right Cessation
- 1985-12-02 JP JP60269533A patent/JPH0764818B2/ja not_active Expired - Lifetime
- 1985-12-02 KR KR1019850009011A patent/KR930001408B1/ko not_active Expired - Lifetime
- 1985-12-02 ES ES549485A patent/ES8701728A1/es not_active Expired
- 1985-12-02 HU HU854595A patent/HU199421B/hu unknown
- 1985-12-02 DK DK556885A patent/DK163184C/da not_active IP Right Cessation
- 1985-12-03 DE DE3542739A patent/DE3542739C2/de not_active Expired - Lifetime
- 1985-12-03 DD DD85283625A patent/DD239792A5/de unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE853019L (en) | 1986-06-03 |
| DK556885A (da) | 1986-06-04 |
| IL77092A0 (en) | 1986-04-29 |
| HUT41389A (en) | 1987-04-28 |
| IL77092A (en) | 1988-12-30 |
| JPH0764818B2 (ja) | 1995-07-12 |
| EP0184027A2 (en) | 1986-06-11 |
| EP0184027A3 (en) | 1987-02-25 |
| HU199421B (en) | 1990-02-28 |
| ES8701728A1 (es) | 1986-12-01 |
| AU5055385A (en) | 1986-06-12 |
| DE3542739A1 (de) | 1986-06-05 |
| DK556885D0 (da) | 1985-12-02 |
| AU576407B2 (en) | 1988-08-25 |
| ZA859223B (en) | 1986-08-27 |
| ES549485A0 (es) | 1986-12-01 |
| DK163184B (da) | 1992-02-03 |
| DK163184C (da) | 1992-06-29 |
| JPS61158966A (ja) | 1986-07-18 |
| EP0184027B1 (en) | 1990-02-07 |
| KR930001408B1 (ko) | 1993-02-27 |
| ATE50247T1 (de) | 1990-02-15 |
| DE3542739C2 (de) | 1997-12-11 |
| CA1332606C (en) | 1994-10-18 |
| KR860004881A (ko) | 1986-07-14 |
| BR8506021A (pt) | 1986-08-19 |
| US4782157A (en) | 1988-11-01 |
| IE58643B1 (en) | 1993-10-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A5 | Published as prov. exclusive patent | ||
| IF04 | In force in the year 2004 |
Expiry date: 20051204 |