IL103461A - 2-(Halomethyl.) nicotinic esters and 2-(halogethyl) benzoic esters useful as intermediates in the preparation of herbicidal compounds - Google Patents
2-(Halomethyl.) nicotinic esters and 2-(halogethyl) benzoic esters useful as intermediates in the preparation of herbicidal compoundsInfo
- Publication number
- IL103461A IL103461A IL10346188A IL10346188A IL103461A IL 103461 A IL103461 A IL 103461A IL 10346188 A IL10346188 A IL 10346188A IL 10346188 A IL10346188 A IL 10346188A IL 103461 A IL103461 A IL 103461A
- Authority
- IL
- Israel
- Prior art keywords
- preparation
- formula
- esters
- intermediates
- compounds
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 18
- 150000002148 esters Chemical class 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title abstract description 15
- 239000000543 intermediate Substances 0.000 title abstract description 7
- 230000002363 herbicidal effect Effects 0.000 title description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 title description 2
- -1 benzoic ester Chemical class 0.000 claims description 3
- 238000000034 method Methods 0.000 abstract description 11
- 239000003795 chemical substances by application Substances 0.000 abstract description 4
- 230000003647 oxidation Effects 0.000 abstract description 2
- 238000007254 oxidation reaction Methods 0.000 abstract description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 1
- VIAIZAVDGKSNBY-UHFFFAOYSA-N 2-[[(1-amino-2,3-dimethyl-1-oxobutan-2-yl)amino]methyl]benzoic acid Chemical compound CC(C)C(C)(C(N)=O)NCC1=CC=CC=C1C(O)=O VIAIZAVDGKSNBY-UHFFFAOYSA-N 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000004970 halomethyl group Chemical group 0.000 description 4
- 235000001968 nicotinic acid Nutrition 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000010586 diagram Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 239000011664 nicotinic acid Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- YCPQUHCGFDFLSI-UHFFFAOYSA-N 2-amino-2,3-dimethylbutanamide Chemical compound CC(C)C(C)(N)C(N)=O YCPQUHCGFDFLSI-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 150000001204 N-oxides Chemical class 0.000 description 2
- WFAULHLDTDDABL-UHFFFAOYSA-N Proxazole citrate Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C=1C=CC=CC=1C(CC)C1=NOC(CCN(CC)CC)=N1 WFAULHLDTDDABL-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- ZYZMTJQOPHVEAX-UHFFFAOYSA-N ethyl 2-(chloromethyl)-5-ethylpyridine-3-carboxylate Chemical compound CCOC(=O)C1=CC(CC)=CN=C1CCl ZYZMTJQOPHVEAX-UHFFFAOYSA-N 0.000 description 2
- 229940064982 ethylnicotinate Drugs 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- VBTQNRFWXBXZQR-UHFFFAOYSA-N n-bromoacetamide Chemical compound CC(=O)NBr VBTQNRFWXBXZQR-UHFFFAOYSA-N 0.000 description 2
- 229960003512 nicotinic acid Drugs 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- YCPQUHCGFDFLSI-LURJTMIESA-N (2s)-2-amino-2,3-dimethylbutanamide Chemical compound CC(C)[C@](C)(N)C(N)=O YCPQUHCGFDFLSI-LURJTMIESA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- VSGNJFMJPJJRTQ-UHFFFAOYSA-N 2-(4,5-dihydroimidazol-1-yl)benzoic acid Chemical class OC(=O)C1=CC=CC=C1N1C=NCC1 VSGNJFMJPJJRTQ-UHFFFAOYSA-N 0.000 description 1
- GMLDCZYTIPCVMO-UHFFFAOYSA-N 2-methylidenebutanal Chemical compound CCC(=C)C=O GMLDCZYTIPCVMO-UHFFFAOYSA-N 0.000 description 1
- HNTZKNJGAFJMHQ-UHFFFAOYSA-N 2-methylpyridine-3-carboxylic acid Chemical compound CC1=NC=CC=C1C(O)=O HNTZKNJGAFJMHQ-UHFFFAOYSA-N 0.000 description 1
- WXYKQNAKEPRCGF-UHFFFAOYSA-N 2-methylquinoline-3-carboxylic acid Chemical compound C1=CC=C2C=C(C(O)=O)C(C)=NC2=C1 WXYKQNAKEPRCGF-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- GEHMBYLTCISYNY-UHFFFAOYSA-N Ammonium sulfamate Chemical compound [NH4+].NS([O-])(=O)=O GEHMBYLTCISYNY-UHFFFAOYSA-N 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- GPDFVBIDCBPHSW-UHFFFAOYSA-N ethyl 2,4-dichloro-3-oxobutanoate Chemical compound CCOC(=O)C(Cl)C(=O)CCl GPDFVBIDCBPHSW-UHFFFAOYSA-N 0.000 description 1
- FYNOJJRGRJQERN-UHFFFAOYSA-N ethyl 2-(chloromethyl)quinoline-3-carboxylate Chemical compound C1=CC=C2N=C(CCl)C(C(=O)OCC)=CC2=C1 FYNOJJRGRJQERN-UHFFFAOYSA-N 0.000 description 1
- XBMKYXSDMNCNOA-UHFFFAOYSA-N ethyl 2-[[(1-amino-2,3-dimethyl-1-oxobutan-2-yl)amino]methyl]-5-ethylpyridine-3-carboxylate Chemical compound CCOC(=O)C1=CC(CC)=CN=C1CNC(C)(C(C)C)C(N)=O XBMKYXSDMNCNOA-UHFFFAOYSA-N 0.000 description 1
- TZORNSWZUZDUCU-UHFFFAOYSA-N ethyl 2-methylpyridine-3-carboxylate Chemical compound CCOC(=O)C1=CC=CN=C1C TZORNSWZUZDUCU-UHFFFAOYSA-N 0.000 description 1
- MHYCRLGKOZWVEF-UHFFFAOYSA-N ethyl acetate;hydrate Chemical compound O.CCOC(C)=O MHYCRLGKOZWVEF-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 150000002814 niacins Chemical class 0.000 description 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
- C07C237/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- 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)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/148,743 US4861887A (en) | 1988-01-27 | 1988-01-27 | Herbicidal o-(substituted, aminomethylbenzoic, nicotinic and quinoline-3-carboxylic acids, esters, and salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL103461A true IL103461A (en) | 1994-06-24 |
Family
ID=22527159
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL10346188A IL103461A (en) | 1988-01-27 | 1988-11-29 | 2-(Halomethyl.) nicotinic esters and 2-(halogethyl) benzoic esters useful as intermediates in the preparation of herbicidal compounds |
| IL88536A IL88536A (en) | 1988-01-27 | 1988-11-29 | Process for the preparation of herbicidal o-carboxylaryl- imidazolinones, and novel intermediates thereof |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL88536A IL88536A (en) | 1988-01-27 | 1988-11-29 | Process for the preparation of herbicidal o-carboxylaryl- imidazolinones, and novel intermediates thereof |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4861887A (da) |
| EP (1) | EP0325730B1 (da) |
| JP (1) | JP2825517B2 (da) |
| KR (1) | KR0130975B1 (da) |
| AT (1) | ATE107288T1 (da) |
| AU (1) | AU618062B2 (da) |
| BR (1) | BR8900317A (da) |
| CA (1) | CA1338248C (da) |
| DE (1) | DE3850240T2 (da) |
| DK (3) | DK34089A (da) |
| ES (1) | ES2054777T3 (da) |
| HU (1) | HU205915B (da) |
| IE (1) | IE64510B1 (da) |
| IL (2) | IL103461A (da) |
| ZA (1) | ZA89643B (da) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5322948A (en) * | 1989-08-31 | 1994-06-21 | Hoechst Celanese Corporation | Process for preparing pyridinecarboxylic acid derivatives |
| US5062881A (en) * | 1989-12-20 | 1991-11-05 | American Cyanamid Company | 2-(1-substituted-2-imidazolin-2-yl)benzoic and nicotinic acids and a method for their preparation |
| ATE166350T1 (de) * | 1989-12-27 | 1998-06-15 | American Cyanamid Co | Alkylester von 5-heterocyclische-pyridin-2,3- dicarbonsäuren und 5-heterocyclische-2-(2- imidazolin-2-yl)pyridinen und verfahren zu ihrer herstellung |
| KR920003063B1 (ko) * | 1990-02-28 | 1992-04-13 | 재단법인 한국화학연구소 | 신규한2-(2-이미다졸린-2-일)-3-(아미노옥소아세틸)-피리딘유도체와그염 |
| US5108485A (en) * | 1990-08-31 | 1992-04-28 | American Cyanamid Company | Herbicidal 2-(2-imidazolin-2-yl)-benzazoles |
| IE913517A1 (en) * | 1991-04-29 | 1992-11-04 | Hoechst Celanese Corp | Process for preparing pyridinecarboxylic acid derivatives |
| JP2001081080A (ja) * | 1999-09-14 | 2001-03-27 | Nissan Chem Ind Ltd | ４（５）−クロロメチル−２−フェニル−１，２，３−トリアゾール誘導体の製造法 |
| AU2011236155B2 (en) | 2010-04-06 | 2014-01-16 | Nippon Soda Co., Ltd. | Nitrogen-containing heterocyclic compound and method for producing same |
| AU2014201036B2 (en) * | 2010-04-06 | 2015-07-16 | Nippon Soda Co., Ltd | Nitrogen-containing heterocyclic compound and method for producing same |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| YU204274A (en) * | 1973-07-24 | 1982-06-30 | Hoechst Ag | Process for preparing new dibenzoxepin derivatives |
| US4188487A (en) * | 1977-08-08 | 1980-02-12 | American Cyanamid Company | Imidazolinyl benzoic acids, esters and salts and their use as herbicidal agents |
| US4297128A (en) * | 1978-06-09 | 1981-10-27 | American Cyanamid Co. | Use of imidazolinyl benzoates as herbicidal agents |
| IL62794A0 (en) * | 1980-06-02 | 1981-07-31 | American Cyanamid Co | Substituted nicotinic acid esters and salts thereof and their use as herbicidal agents |
| 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 |
| HU191626B (en) * | 1982-05-25 | 1987-03-30 | American Cyanamid Co | Process for preparing 2-/5,5-disubstituted-4-oxo-2-imidazolin-2-il/-benzoic acid, -nicotinic acid and -quinoline-3-carboxylic acid derivatives |
| DE3345901A1 (de) * | 1983-12-20 | 1985-06-27 | Hoechst Ag, 6230 Frankfurt | 1-acylimidazolinone, verfahren zu ihrer herstellung und ihre verwendung in der landwirtschaft |
| EP0158000B1 (en) * | 1984-02-10 | 1991-06-19 | American Cyanamid Company | Regio and optical isomers of imidazolinyl toluic acids, esters and salts, their method of preparation and their use as herbicidal agents |
| 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 |
| EP0261705A1 (en) * | 1986-08-25 | 1988-03-30 | Shell Internationale Researchmaatschappij B.V. | Herbicidal imidazolinyl benzoic acids and derivatives |
| US4689425A (en) * | 1986-11-06 | 1987-08-25 | Stauffer Chemical Company | Photochlorination of aromatic compounds in the side chain |
-
1988
- 1988-01-27 US US07/148,743 patent/US4861887A/en not_active Expired - Lifetime
- 1988-11-29 EP EP88119865A patent/EP0325730B1/en not_active Expired - Lifetime
- 1988-11-29 ES ES88119865T patent/ES2054777T3/es not_active Expired - Lifetime
- 1988-11-29 IL IL10346188A patent/IL103461A/en not_active IP Right Cessation
- 1988-11-29 IL IL88536A patent/IL88536A/xx not_active IP Right Cessation
- 1988-11-29 AT AT88119865T patent/ATE107288T1/de not_active IP Right Cessation
- 1988-11-29 DE DE3850240T patent/DE3850240T2/de not_active Expired - Fee Related
-
1989
- 1989-01-24 JP JP1013331A patent/JP2825517B2/ja not_active Expired - Lifetime
- 1989-01-25 HU HU89316A patent/HU205915B/hu not_active IP Right Cessation
- 1989-01-25 AU AU28787/89A patent/AU618062B2/en not_active Ceased
- 1989-01-25 CA CA000589101A patent/CA1338248C/en not_active Expired - Fee Related
- 1989-01-26 BR BR898900317A patent/BR8900317A/pt not_active IP Right Cessation
- 1989-01-26 ZA ZA89643A patent/ZA89643B/xx unknown
- 1989-01-26 KR KR1019890000811A patent/KR0130975B1/ko not_active Expired - Fee Related
- 1989-01-26 IE IE23189A patent/IE64510B1/en not_active IP Right Cessation
- 1989-01-26 DK DK034089A patent/DK34089A/da not_active Application Discontinuation
-
1993
- 1993-05-04 DK DK050793A patent/DK50793A/da unknown
- 1993-05-04 DK DK93506A patent/DK50693D0/da not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0325730A3 (en) | 1991-02-13 |
| IE890231L (en) | 1989-07-27 |
| IE64510B1 (en) | 1995-08-09 |
| US4861887A (en) | 1989-08-29 |
| EP0325730B1 (en) | 1994-06-15 |
| DK50793D0 (da) | 1993-05-04 |
| KR0130975B1 (ko) | 1998-04-16 |
| IL88536A (en) | 1993-02-21 |
| DK50693A (da) | 1993-05-04 |
| DK50793A (da) | 1993-05-04 |
| JPH01224364A (ja) | 1989-09-07 |
| KR890011873A (ko) | 1989-08-23 |
| EP0325730A2 (en) | 1989-08-02 |
| ES2054777T3 (es) | 1994-08-16 |
| DK34089D0 (da) | 1989-01-26 |
| ZA89643B (en) | 1989-10-25 |
| ATE107288T1 (de) | 1994-07-15 |
| DE3850240D1 (de) | 1994-07-21 |
| IL88536A0 (en) | 1989-06-30 |
| HUT50133A (en) | 1989-12-28 |
| DK34089A (da) | 1989-07-28 |
| BR8900317A (pt) | 1989-09-19 |
| HU205915B (en) | 1992-07-28 |
| CA1338248C (en) | 1996-04-16 |
| DE3850240T2 (de) | 1995-02-02 |
| JP2825517B2 (ja) | 1998-11-18 |
| DK50693D0 (da) | 1993-05-04 |
| AU2878789A (en) | 1989-07-27 |
| AU618062B2 (en) | 1991-12-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0806414B1 (en) | Intermediates for herbicidal carboxamide derivatives | |
| US6441190B1 (en) | Process of the preparation of chiral nicotinic, quinolinic or benzoic acid imidazolinone herbicides | |
| IL135795A (en) | Process for the preparation of chiral imidazolinone herbicides | |
| IL103461A (en) | 2-(Halomethyl.) nicotinic esters and 2-(halogethyl) benzoic esters useful as intermediates in the preparation of herbicidal compounds | |
| EP0095105B1 (en) | Process for the preparation of 2-(5,5-disubstituted-4-oxo-2-imidazolin-2-yl)-nicotinic acids, quinoline-3-carboxylic acids, and benzoic acids | |
| JPH0762003B2 (ja) | ５−オキソ−イミダゾリニル安息香酸類、ニコチン酸類及びキノリンカルボン酸類の製造法 | |
| HU195953B (en) | Process for producing occasionally substituted 2-carbamoyl-nicotinic acids, -3-quinolinecarboxylic acids and occasionally their optical isomers | |
| EP0142718B1 (en) | Preparation of substituted and unsubstituted 2-((1-carbamoyl-1,2-dimethylpropyl)-carbamoyl)-3-quinolinecarboxylic, nicotinic and benzoic acids | |
| KR930001408B1 (ko) | 치환 및 비치환 2-카르바모일 니코틴산 및 3-퀴놀린 카르복실산의 제조방법 | |
| US4959476A (en) | Method for the preparation of herbicidal O-carboxyarylimidazolinones | |
| EP0388620B1 (en) | Process for the preparation of o-carboxypyridyl- and o-carboxyquinolylimidazolinones | |
| US5103009A (en) | Method for the preparation of herbicidal intermediates | |
| US4645836A (en) | Process for the preparation of 6,7-dihydroxy-4-alkyl-2(1H) quinazolinone-1-propionic acids | |
| US5034532A (en) | Method for the preparation of quinolyl and pyridyl substituted imidazolinones | |
| KR0134906B1 (ko) | 제초제로서 유용한 o-카르복시아릴이미다졸리논 화합물의 중간체 및 그 제조방법 | |
| RU2228929C2 (ru) | Способ получения 3s-3-амино-3-пиридилпропионовой кислоты и ее производных и промежуточное вещество | |
| EP0145334A2 (en) | Benzaldehyde derivative and process for its preparation | |
| US4904816A (en) | Process for the manufacture of anilinofumarate via chloromaleate or chlorofumarate or mixtures thereof | |
| KR900003391B1 (ko) | 2-(5,5-디치환-4-옥소-2-이미다졸린-2-일)니코틴산 및 퀴놀린-3-카복실산류의 제법 | |
| US5001254A (en) | Novel method for the preparation of quinoline-2,3-dicarboxylic | |
| KR860000782B1 (ko) | 퀴놀린 카르복실산 유도체의 제조방법 | |
| KR870001043B1 (ko) | 2-아닐리노니코틴산의 아실옥시알킬 에스테르의 제조방법 | |
| US4526975A (en) | 2-Amino-4-(4-pyridinyl)benzoic acids | |
| NZ202320A (en) | Anthraniloyloxyalkanoates and pharmaceutical compositions containing such | |
| KR20050108739A (ko) | E형의 2-벤조일-3-디메틸아미노아크릴레이트 유도체의 제조방법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RH1 | Patent not in force |