TWI223650B - A process for the preparation of chiral imidazolinone herbicides - Google Patents
A process for the preparation of chiral imidazolinone herbicides Download PDFInfo
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- TWI223650B TWI223650B TW089108313A TW89108313A TWI223650B TW I223650 B TWI223650 B TW I223650B TW 089108313 A TW089108313 A TW 089108313A TW 89108313 A TW89108313 A TW 89108313A TW I223650 B TWI223650 B TW I223650B
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- Taiwan
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- 238000000034 method Methods 0.000 title claims abstract description 35
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 239000004009 herbicide Substances 0.000 title claims abstract description 6
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 title claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 17
- 239000002904 solvent Substances 0.000 claims abstract description 13
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 238000009835 boiling Methods 0.000 claims abstract 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 11
- 239000002585 base Substances 0.000 claims description 11
- -1 4-isopropylmethyl-5-ketonicotinic acid Chemical compound 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 7
- 230000002363 herbicidal effect Effects 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 4
- 229930195733 hydrocarbon Chemical class 0.000 claims description 4
- 150000002430 hydrocarbons Chemical class 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 229960003512 nicotinic acid Drugs 0.000 claims description 3
- 235000001968 nicotinic acid Nutrition 0.000 claims description 3
- 239000011664 nicotinic acid Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000005690 diesters Chemical class 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 150000002170 ethers Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 2
- DCKOJKCSWDKXIF-UHFFFAOYSA-N 4-methyl-4-propan-2-yl-1h-imidazol-5-one Chemical compound CC(C)C1(C)N=CNC1=O DCKOJKCSWDKXIF-UHFFFAOYSA-N 0.000 claims 2
- 150000001340 alkali metals Chemical class 0.000 claims 2
- 150000004703 alkoxides Chemical class 0.000 claims 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims 2
- 235000021314 Palmitic acid Nutrition 0.000 claims 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical group CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 235000021478 household food Nutrition 0.000 claims 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- YCPQUHCGFDFLSI-ZCFIWIBFSA-N (2r)-2-amino-2,3-dimethylbutanamide Chemical compound CC(C)[C@@](C)(N)C(N)=O YCPQUHCGFDFLSI-ZCFIWIBFSA-N 0.000 abstract description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 239000011260 aqueous acid Substances 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-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
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000004445 quantitative analysis Methods 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- CABMTIJINOIHOD-QGZVFWFLSA-N (R)-imazaquin Chemical compound N1C(=O)[C@](C(C)C)(C)N=C1C1=NC2=CC=CC=C2C=C1C(O)=O CABMTIJINOIHOD-QGZVFWFLSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- PDQRQJVPEFGVRK-UHFFFAOYSA-N 2,1,3-benzothiadiazole Chemical class C1=CC=CC2=NSN=C21 PDQRQJVPEFGVRK-UHFFFAOYSA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- IWTBVKIGCDZRPL-LURJTMIESA-N 3-Methylbutanol Natural products CC[C@H](C)CCO IWTBVKIGCDZRPL-LURJTMIESA-N 0.000 description 1
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 1
- HINMGNHBDCADKG-UHFFFAOYSA-N 5-propan-2-yl-1h-imidazole Chemical compound CC(C)C1=CNC=N1 HINMGNHBDCADKG-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
- SHIYFJVPSJMNJE-UHFFFAOYSA-N N1=C(C=CC=C1)CC1=CC=CC=2C3=CC=CC=C3CC1=2 Chemical compound N1=C(C=CC=C1)CC1=CC=CC=2C3=CC=CC=C3CC1=2 SHIYFJVPSJMNJE-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 239000002027 dichloromethane extract Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical group [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- VRAOQOFWZFIOSZ-UHFFFAOYSA-N osmium potassium Chemical group [K].[Os] VRAOQOFWZFIOSZ-UHFFFAOYSA-N 0.000 description 1
- 229940097411 palm acid Drugs 0.000 description 1
- XDRYMKDFEDOLFX-UHFFFAOYSA-N pentamidine Chemical compound C1=CC(C(=N)N)=CC=C1OCCCCCOC1=CC=C(C(N)=N)C=C1 XDRYMKDFEDOLFX-UHFFFAOYSA-N 0.000 description 1
- 229960004448 pentamidine Drugs 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- DYVOLUUJJDFBFC-UHFFFAOYSA-N tripotassium butan-1-olate Chemical compound [K+].[K+].[K+].CCCC[O-].CCCC[O-].CCCC[O-] DYVOLUUJJDFBFC-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/06—Nitrogen directly attached to an aromatic ring system
-
- 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)
- 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)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/303,967 US5973154A (en) | 1999-05-03 | 1999-05-03 | Process for the preparation of chiral imidazolinone herbicides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI223650B true TWI223650B (en) | 2004-11-11 |
Family
ID=23174474
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW089108313A TWI223650B (en) | 1999-05-03 | 2000-05-02 | A process for the preparation of chiral imidazolinone herbicides |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US5973154A (OSRAM) |
| EP (1) | EP1050533A1 (OSRAM) |
| JP (1) | JP2000319276A (OSRAM) |
| KR (1) | KR20010029680A (OSRAM) |
| CN (1) | CN1272496A (OSRAM) |
| AR (1) | AR025522A1 (OSRAM) |
| AU (1) | AU3024300A (OSRAM) |
| BR (1) | BR0002073A (OSRAM) |
| CA (1) | CA2307391C (OSRAM) |
| HU (1) | HUP0001710A3 (OSRAM) |
| IL (1) | IL135795A (OSRAM) |
| IN (1) | IN187740B (OSRAM) |
| MX (1) | MXPA00004111A (OSRAM) |
| NZ (1) | NZ504204A (OSRAM) |
| PL (1) | PL339971A1 (OSRAM) |
| SK (1) | SK6002000A3 (OSRAM) |
| TW (1) | TWI223650B (OSRAM) |
| ZA (1) | ZA200002131B (OSRAM) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2313322T5 (es) | 2004-04-01 | 2017-09-06 | Basf Agrochemical Products, B.V. | Mezclas herbicidas que actúan sinérgicamente |
| EP1976383A2 (en) * | 2005-12-23 | 2008-10-08 | Basf Se | A method for controlling aquatic weeds |
| EP1965641B1 (en) * | 2005-12-23 | 2009-10-07 | Basf Se | A method of controlling the aquatic weed hydrilla verticillata |
| US9210930B2 (en) * | 2005-12-23 | 2015-12-15 | Basf Se | Control of submerged aquatic vegetation |
| MX2008012191A (es) * | 2006-04-07 | 2008-10-02 | Basf Se | Mezcla herbicida, que comprende un herbicida de imidazolinona y un adyuvante. |
| HUE037228T2 (hu) | 2008-06-18 | 2018-08-28 | Basf Se | Aminopiralidot és imazamoxot tartalmazó háromkomponensû herbicid készítmények |
| WO2010054952A1 (en) * | 2008-11-13 | 2010-05-20 | Basf Se | 2-[(1-cyanopropyl)carbamoyl]-5-chloromethyl nicotinic acids and the use thereof in manufacturing herbicidal imidazolinones |
| WO2010055042A1 (en) * | 2008-11-13 | 2010-05-20 | Basf Se | 2-[(1-cyanopropyl)carbamoyl]-5-methoxymethyl nicotinic acids and the use thereof in manufacturing herbicidal imidazolinones |
| CN102245578B (zh) * | 2008-11-13 | 2015-01-07 | 巴斯夫欧洲公司 | 制备5-氯甲基-2,3-吡啶二甲酸酐的方法 |
| WO2010132873A2 (en) * | 2009-05-15 | 2010-11-18 | Northwestern University | Chiral pyrrolidine core compounds en route to inhibitors of nitric oxide synthase |
| US20130157856A1 (en) | 2010-08-24 | 2013-06-20 | Basf Se | Agrochemical Mixtures for Increasing the Health of a Plant |
| HUE034959T2 (en) | 2011-12-05 | 2018-05-02 | Basf Agrochemical Products Bv | Procedure for controlling undesirable vegetation with imazamox and adjuvants in herbicide-resistant crops |
| WO2018091964A1 (en) | 2016-11-21 | 2018-05-24 | Adama Agan Ltd. | Process for preparing methoxy methyl pyridine dicarboxylate |
| WO2020126578A1 (en) | 2018-12-18 | 2020-06-25 | Basf Agrochemical Products B.V. | Herbicidal combinations |
| EP3897139A1 (en) | 2018-12-18 | 2021-10-27 | BASF Agrochemical Products B.V. | Herbicidal combinations |
| EA202191655A1 (ru) | 2018-12-18 | 2021-11-01 | Басф Агрокемикэл Продактс Б.В. | Гербицидные комбинации |
| EP3897141A1 (en) | 2018-12-18 | 2021-10-27 | BASF Agrochemical Products B.V. | Herbicidal combinations |
| EP3897151A1 (en) | 2018-12-18 | 2021-10-27 | BASF Agrochemical Products B.V. | Herbicidal composition |
| EP3897138A1 (en) | 2018-12-18 | 2021-10-27 | BASF Agrochemical Products B.V. | Herbicidal combinations |
| RU2707043C1 (ru) * | 2019-03-25 | 2019-11-21 | Акционерное общество "Щелково Агрохим" | Способ получения гербицида имазамокса |
| CN113061125B (zh) * | 2019-12-13 | 2022-11-01 | 沈阳中化农药化工研发有限公司 | 一种咪唑啉酮化合物的制备方法 |
| CN113620928A (zh) * | 2021-08-16 | 2021-11-09 | 辽宁先达农业科学有限公司 | 一种甲氧咪草烟钠盐的合成方法 |
| CN118019453A (zh) | 2021-09-28 | 2024-05-10 | 巴斯夫农业化学品有限公司 | 用于控制马唐属草的甲氧咪草烟和草甘膦 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4683324A (en) * | 1982-05-25 | 1987-07-28 | American Cyanamid Company | Process for the resolution of certain racemic amino nitriles |
| DE3420271C2 (de) * | 1983-06-02 | 1994-05-26 | American Cyanamid Co | (2-Imidazolin-2-yl)thieno- und -furo[2,3-b] und [3,2-b] Pyridine und ein Verfahren zur Herstellung derselben, sowie die Verwendung dieser Verbindungen als herbizide Mittel |
| EP0233150B1 (de) * | 1986-02-10 | 1992-11-11 | Ciba-Geigy Ag | Verfahren zur Herstellung von 2-(Imidazolin-2-yl)-pyridin- und -chinolin-3-carbonsäuren |
| EP0296109A3 (de) * | 1987-06-18 | 1989-12-20 | Ciba-Geigy Ag | 2-(Imidazolin-2-yl)nicotinsäurederivate |
| US4925944A (en) * | 1989-03-21 | 1990-05-15 | American Cyanamid Company | Process for the preparation of o-carboxypyridyl- and o-carboxyquinolylimidazolinones |
-
1999
- 1999-05-03 US US09/303,967 patent/US5973154A/en not_active Expired - Fee Related
-
2000
- 2000-04-24 IL IL13579500A patent/IL135795A/en active IP Right Grant
- 2000-04-25 JP JP2000123949A patent/JP2000319276A/ja not_active Withdrawn
- 2000-04-26 SK SK600-2000A patent/SK6002000A3/sk unknown
- 2000-04-27 CN CN00108177A patent/CN1272496A/zh active Pending
- 2000-04-27 NZ NZ504204A patent/NZ504204A/en unknown
- 2000-04-27 MX MXPA00004111A patent/MXPA00004111A/es unknown
- 2000-04-28 EP EP00303585A patent/EP1050533A1/en not_active Ceased
- 2000-04-28 PL PL00339971A patent/PL339971A1/xx not_active Application Discontinuation
- 2000-05-01 KR KR1020000023246A patent/KR20010029680A/ko not_active Ceased
- 2000-05-01 IN IN257CA2000 patent/IN187740B/en unknown
- 2000-05-01 CA CA002307391A patent/CA2307391C/en not_active Expired - Fee Related
- 2000-05-02 ZA ZA200002131A patent/ZA200002131B/xx unknown
- 2000-05-02 AU AU30243/00A patent/AU3024300A/en not_active Abandoned
- 2000-05-02 BR BR0002073-7A patent/BR0002073A/pt not_active Application Discontinuation
- 2000-05-02 HU HU0001710A patent/HUP0001710A3/hu unknown
- 2000-05-02 AR ARP000102094A patent/AR025522A1/es unknown
- 2000-05-02 TW TW089108313A patent/TWI223650B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| US5973154A (en) | 1999-10-26 |
| AU3024300A (en) | 2000-11-09 |
| CA2307391C (en) | 2008-07-08 |
| IL135795A0 (en) | 2001-05-20 |
| ZA200002131B (en) | 2000-11-07 |
| IL135795A (en) | 2004-05-12 |
| HU0001710D0 (en) | 2000-06-28 |
| CA2307391A1 (en) | 2000-11-03 |
| JP2000319276A (ja) | 2000-11-21 |
| KR20010029680A (ko) | 2001-04-06 |
| PL339971A1 (en) | 2000-11-06 |
| MXPA00004111A (es) | 2002-07-22 |
| SK6002000A3 (en) | 2000-12-11 |
| AR025522A1 (es) | 2002-12-04 |
| CN1272496A (zh) | 2000-11-08 |
| HUP0001710A2 (hu) | 2001-05-28 |
| IN187740B (OSRAM) | 2002-06-15 |
| HUP0001710A3 (en) | 2002-12-28 |
| BR0002073A (pt) | 2001-01-02 |
| NZ504204A (en) | 2001-09-28 |
| EP1050533A1 (en) | 2000-11-08 |
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| MM4A | Annulment or lapse of patent due to non-payment of fees |