DE3051172C2 - - Google Patents
Info
- Publication number
- DE3051172C2 DE3051172C2 DE3051172A DE3051172A DE3051172C2 DE 3051172 C2 DE3051172 C2 DE 3051172C2 DE 3051172 A DE3051172 A DE 3051172A DE 3051172 A DE3051172 A DE 3051172A DE 3051172 C2 DE3051172 C2 DE 3051172C2
- Authority
- DE
- Germany
- Prior art keywords
- compound
- formula
- ether
- compounds
- mixture
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 11
- 230000002363 herbicidal effect Effects 0.000 claims description 8
- VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 229960000990 monobenzone Drugs 0.000 claims description 4
- -1 Heterocyclic ether compound Chemical class 0.000 claims description 3
- 229940053200 antiepileptics fatty acid derivative Drugs 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 239000013078 crystal Substances 0.000 description 7
- 239000004009 herbicide Substances 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 235000011181 potassium carbonates Nutrition 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 150000007529 inorganic bases Chemical class 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 150000007530 organic bases Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- CQWFZBPLGQDNQW-UHFFFAOYSA-N 4-quinolin-2-yloxyphenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(C=CC=C2)C2=N1 CQWFZBPLGQDNQW-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- YGHJGQYNECSZDY-LLVKDONJSA-N methyl (2r)-2-[4-(6-chloroquinoxalin-2-yl)oxyphenoxy]propanoate Chemical compound C1=CC(O[C@H](C)C(=O)OC)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 YGHJGQYNECSZDY-LLVKDONJSA-N 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- JLJCUGQBTWIIKL-UHFFFAOYSA-N 2-(4-phenylmethoxyphenoxy)quinoline Chemical compound C=1C=C(OC=2N=C3C=CC=CC3=CC=2)C=CC=1OCC1=CC=CC=C1 JLJCUGQBTWIIKL-UHFFFAOYSA-N 0.000 description 1
- ZEDHSSVDQTYBRV-UHFFFAOYSA-N 2-bromo-n,n-dimethylpropanamide Chemical compound CC(Br)C(=O)N(C)C ZEDHSSVDQTYBRV-UHFFFAOYSA-N 0.000 description 1
- QQEWXGTYYUSXII-UHFFFAOYSA-N 2-chloro-6-fluoroquinoxaline Chemical compound N1=C(Cl)C=NC2=CC(F)=CC=C21 QQEWXGTYYUSXII-UHFFFAOYSA-N 0.000 description 1
- OFUFXTHGZWIDDB-UHFFFAOYSA-N 2-chloroquinoline Chemical compound C1=CC=CC2=NC(Cl)=CC=C21 OFUFXTHGZWIDDB-UHFFFAOYSA-N 0.000 description 1
- BSDZLWKEACOABU-UHFFFAOYSA-N 2-phenoxyquinoxaline Chemical compound C=1N=C2C=CC=CC2=NC=1OC1=CC=CC=C1 BSDZLWKEACOABU-UHFFFAOYSA-N 0.000 description 1
- MNYCPGVPVPAADT-UHFFFAOYSA-N 4-(6-fluoroquinoxalin-2-yl)oxyphenol Chemical compound C1=CC(O)=CC=C1OC1=CN=C(C=C(F)C=C2)C2=N1 MNYCPGVPVPAADT-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241001148683 Zostera marina Species 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006264 debenzylation reaction Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- ARFLASKVLJTEJD-UHFFFAOYSA-N ethyl 2-bromopropanoate Chemical compound CCOC(=O)C(C)Br ARFLASKVLJTEJD-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 238000003898 horticulture Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- LPEKGGXMPWTOCB-VKHMYHEASA-N methyl (S)-lactate Chemical compound COC(=O)[C@H](C)O LPEKGGXMPWTOCB-VKHMYHEASA-N 0.000 description 1
- ACEONLNNWKIPTM-UHFFFAOYSA-N methyl 2-bromopropanoate Chemical compound COC(=O)C(C)Br ACEONLNNWKIPTM-UHFFFAOYSA-N 0.000 description 1
- SUYPCAPCUOHMFB-UHFFFAOYSA-N n,n-dimethyl-2-(4-quinolin-2-yloxyphenoxy)propanamide Chemical compound C1=CC(OC(C)C(=O)N(C)C)=CC=C1OC1=CC=C(C=CC=C2)C2=N1 SUYPCAPCUOHMFB-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- GHKGUEZUGFJUEJ-UHFFFAOYSA-M potassium;4-methylbenzenesulfonate Chemical compound [K+].CC1=CC=C(S([O-])(=O)=O)C=C1 GHKGUEZUGFJUEJ-UHFFFAOYSA-M 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
-
- 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
- A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines 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 carbon atoms of the hetero ring
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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP54020164A JPS6033389B2 (ja) | 1979-02-22 | 1979-02-22 | 複素環エ−テル系フェノシキ脂肪酸誘導体、その製造法および該誘導体を含有する除草剤 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3051172C2 true DE3051172C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1993-01-28 |
Family
ID=12019508
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3051251A Expired - Lifetime DE3051251C2 (de) | 1979-02-22 | 1980-02-08 | Herbizide Mittel, enthaltend Phenoxyfettsäurederivate vom Typ heterocyclischer Ether |
| DE19803004770 Granted DE3004770A1 (de) | 1979-02-22 | 1980-02-08 | Phenoxyfettsaeurederivate vom typ heterocyclischer aether und herbizide mittel mit einem gehalt derselben |
| DE3051172A Expired - Lifetime DE3051172C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-02-22 | 1980-02-08 |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3051251A Expired - Lifetime DE3051251C2 (de) | 1979-02-22 | 1980-02-08 | Herbizide Mittel, enthaltend Phenoxyfettsäurederivate vom Typ heterocyclischer Ether |
| DE19803004770 Granted DE3004770A1 (de) | 1979-02-22 | 1980-02-08 | Phenoxyfettsaeurederivate vom typ heterocyclischer aether und herbizide mittel mit einem gehalt derselben |
Country Status (23)
Families Citing this family (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ194196A (en) * | 1979-07-17 | 1983-07-15 | Ici Australia Ltd | -(quinoxalin-2-yl(oxy or thio) phen (oxy or ylthio)-alkanoic acid derivatives or precursors |
| US4738710A (en) * | 1979-11-19 | 1988-04-19 | Ici Australia Limited | Herbicidal alkane carboxylic acid derivatives |
| AU541697B2 (en) * | 1979-11-19 | 1985-01-17 | Ici Australia Limited | Quinoline derivatives |
| US4609396A (en) * | 1980-06-23 | 1986-09-02 | E. I. Du Pont De Nemours And Company | Quinoxalinyloxy ethers as selective weed control agents |
| CA1317299C (en) * | 1980-06-23 | 1993-05-04 | Maged Mohamed Fawzi | Quinoxalinyloxy ethers as selective weed control agents |
| NZ197420A (en) * | 1980-07-01 | 1984-04-27 | Ici Australia Ltd | -(quinazolin-(2-or 4-)(oxy,ylthio or amino)phen(oxy or ylthio)alkanoic acid derivatives |
| NZ197419A (en) * | 1980-07-01 | 1984-08-24 | Ici Australia Ltd | Omega-(cinnolin-(2 or 3-)yl(oxy,thio or amino)phen-(oxy or ylthio))alkanoic acid derivatives |
| EP0048539B1 (en) * | 1980-07-01 | 1985-08-28 | Ici Australia Limited | Isoquinolyloxy(amino)phenoxyalkane carboxylic acid derivatives, process for their synthesis, herbicidal compositions containing them and their use as herbicides |
| US6197728B1 (en) | 1980-08-06 | 2001-03-06 | Nissan Chemical Industries Ltd. | Quinoxaline derivatives and herbicidal composition |
| US5364831A (en) * | 1980-08-06 | 1994-11-15 | Nissan Chemical Industries Ltd. | Quinoxaline derivatives and herbicidal composition |
| EP0046468A1 (en) * | 1980-08-21 | 1982-03-03 | Nissan Chemical Industries Ltd. | Quinoxaline derivatives and herbicidal composition |
| DE3170423D1 (en) * | 1980-11-26 | 1985-06-13 | Hoffmann La Roche | Oxime esters, processes for their preparation, their use and compositions containing these esters |
| NZ199342A (en) * | 1981-01-12 | 1985-08-16 | Ici Australia Ltd | Quinoxaline derivatives and herbicides |
| US4391628A (en) * | 1981-02-16 | 1983-07-05 | Ciba-Geigy Corporation | 2-[4-(6-Haloquinoxalinyl-2-oxy)phenoxy]propionic acid esters |
| NZ200031A (en) * | 1981-04-02 | 1984-11-09 | Ici Australia Ltd | Quinoline derivatives and herbicidal compositions containing such |
| AU590676B2 (en) * | 1981-04-02 | 1989-11-09 | Ici Australia Limited | Herbicidal quinoline derivatives |
| IL67463A (en) * | 1981-12-17 | 1985-12-31 | Du Pont | 2-alkoxyethoxyethyl 2-(4-(6-halo-2-quinoxy alinyloxy)phenoxy)propanoates and herbicidal compositions containing them |
| JPS5929604A (ja) * | 1982-08-13 | 1984-02-16 | Nissan Chem Ind Ltd | 水性懸濁除草組成物 |
| EP0305593A3 (de) | 1983-12-06 | 1989-10-11 | Ciba-Geigy Ag | Neue Zwischenprodukte für 2-Pyridinyloxyphenoxypropionsäure-cyanamide |
| EP0159290A1 (de) * | 1984-03-28 | 1985-10-23 | Ciba-Geigy Ag | Verwendung von Chinolinderivaten zum Schützen von Kulturpflanzen |
| NO174506B (no) * | 1984-10-30 | 1994-02-07 | Usv Pharma Corp | Analogifremgangsmaate ved fremstilling av terapeutisk aktive forbindelser |
| JPS62190172A (ja) * | 1986-02-14 | 1987-08-20 | Teijin Ltd | フエノキシ脂肪族カルボン酸誘導体および除草剤 |
| US4976772A (en) * | 1986-08-29 | 1990-12-11 | The Dow Chemical Company | 4-((aryloxy)phenoxy)alkenol as intermediates and herbicides |
| US4900354A (en) * | 1986-08-29 | 1990-02-13 | The Dow Chemical Company | (Quinolinyl and quinoxalinyloxy)phenoxy alkenols and their use as post emergent herbicides |
| EP0270378A3 (en) * | 1986-12-05 | 1988-09-07 | E.I. Du Pont De Nemours And Company | Herbicidal aryloxybenzeneacetic acid derivatives |
| ATE93857T1 (de) * | 1988-01-06 | 1993-09-15 | Uniroyal Chem Co Inc | Herbizide heterozyklisch-alkylenchinoxalinyloxyphenoxy propansaeureester. |
| US5319102A (en) * | 1988-01-06 | 1994-06-07 | Uniroyal Chemical Company, Inc. | Heterocyclic-alkylene quinoxalinyloxyphenoxypropanoate herbicides |
| US5120348A (en) * | 1988-01-06 | 1992-06-09 | Uniroyal Chemical Company, Inc. | Heterocyclic-alkylene quinoxalinyloxyphenoxypropanoate herbicides |
| DE3806294A1 (de) * | 1988-02-27 | 1989-09-07 | Hoechst Ag | Herbizide mittel in form von waessrigen mikroemulsionen |
| US4897481A (en) * | 1988-05-31 | 1990-01-30 | The Dow Chemical Company | Process for the minimization of racemization in the preparation of optically active ((aryloxy)phenoxy)propionate herbicides |
| DE3902439A1 (de) * | 1989-01-27 | 1990-08-02 | Basf Ag | Pflanzenschuetzende mittel auf basis von 1-aryl- bzw. 1-hetarylimidazolcarbonsaeureestern |
| DE3907938A1 (de) * | 1989-03-11 | 1990-09-13 | Basf Ag | 2,3-substituierte 1,8-naphthyridine, verfahren zu ihrer herstellung und ihre verwendung als antidots |
| DE4042098C2 (de) * | 1990-12-28 | 1993-10-07 | Hoechst Ag | Verfahren zur Herstellung optisch aktiver Chinoxalinyloxy-phenoxypropionsäureester |
| AU5686794A (en) * | 1992-12-15 | 1994-07-04 | Du Pont Merck Pharmaceutical Company, The | (2-quinoxalinyloxy)phenoxypropanoic acids and related derivatives as anticancer agents |
| DE4318092C1 (de) * | 1993-06-01 | 1995-01-12 | Basf Ag | Verfahren zur Herstellung von (R)- oder (S)-2-(4-Alkanoylphenoxy)- und (R)- oder (S)-2-(4-Aroylphenoxy)-propionsäureestern |
| US5637553A (en) * | 1994-08-19 | 1997-06-10 | Platte Chemical Company | Herbicide and fertilizer composition and method of using same |
| US5541152A (en) * | 1994-08-19 | 1996-07-30 | Platte Chemical Company | Herbicide and fertilizer composition and method of using same |
| AU742672B2 (en) * | 1997-07-11 | 2002-01-10 | Nissan Chemical Industries Ltd. | Aqueous suspension-type pesticide composition |
| AU2001245353A1 (en) * | 2000-02-29 | 2001-09-12 | Cor Therapeutics, Inc. | Benzamides and related inhibitors of factor xa |
| HUP0401562A2 (hu) * | 2001-07-31 | 2004-12-28 | Wayne State University | Kinolinszármazékok és alkalmazásuk tumorellenes szerekként és ezeket tartalmazó gyógyászati készítmények |
| JP2003128501A (ja) * | 2001-10-18 | 2003-05-08 | Nissan Chem Ind Ltd | 農薬乳剤組成物 |
| UA79293C2 (en) * | 2002-07-03 | 2007-06-11 | Univ Wayne State | 4-(7'-halo-2-quino (xa-) linyloxy)phenoxy propionic acid derivatives as antineoplastic agents |
| US7470788B2 (en) * | 2005-09-07 | 2008-12-30 | Wayne State University | Antitumor agents |
| US8183379B2 (en) * | 2005-09-07 | 2012-05-22 | Wayne State University | Antitumor agents |
| JO2685B1 (en) * | 2006-12-06 | 2013-03-03 | جانسين فارماسوتيكا ان في | Quinoline antibacterial derivatives |
| EP2052607A1 (de) | 2007-10-24 | 2009-04-29 | Bayer CropScience AG | Herbizid-Kombination |
| DE102008037622A1 (de) | 2008-08-14 | 2010-02-25 | Bayer Cropscience Ag | Herbizid-Kombination mit Dimethoxytriazinyl-substituierten Difluormethansulfonylaniliden |
| CN106632007B (zh) * | 2016-12-15 | 2019-12-31 | 三峡大学 | 吡啶-3-基芳氧基苯氧基烷酸酯化合物及其应用 |
| CN106699648B (zh) * | 2016-12-15 | 2019-10-08 | 三峡大学 | 2-（4-芳氧基苯氧基）烷酸萘酯化合物及其应用 |
| CN106632293B (zh) * | 2016-12-15 | 2019-02-26 | 三峡大学 | 具有生物活性的芳氧苯氧烷酸衍生物及其制备方法 |
| CN115322159B (zh) * | 2022-06-17 | 2024-01-30 | 聊城大学 | (r)-2-[4-((喹唑啉-4-酮)-2-氧基)苯氧基]丙酸酯衍生物及其应用 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2609461A1 (de) * | 1976-03-08 | 1977-09-22 | Hoechst Ag | Phenoxy-phenoxy-alkancarbonsaeurederivate |
| GB1491274A (en) * | 1974-10-17 | 1977-11-09 | Ishihara Mining & Chemical Co | Substituted(pyridyl-2-oxy)phenoxy alkane carboxylic acid derivatives and their use as herbicides |
| US4130431A (en) * | 1976-07-05 | 1978-12-19 | Kansai Paint Co., Ltd. | Metal surface treatment liquid and rust preventive paint |
| EP0000176A1 (de) * | 1977-06-29 | 1979-01-10 | Ciba-Geigy Ag | Pyridyloxy-phenoxy-alkancarbonsäurederivate, Verfahren zu deren Herstellung, und deren Verwendung als Herbizide oder als pflanzenwachstumsregulierende Mittel |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL260074A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1960-01-14 | |||
| NL297470A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1962-09-05 | |||
| US3415878A (en) * | 1962-09-10 | 1968-12-10 | Geigy Chem Corp | Process for the production of alkali metal salts of nitrilo triacetic acid |
| US3472848A (en) * | 1966-11-17 | 1969-10-14 | Merck & Co Inc | 3-hydroxy and 3-mercapto-pyrazinoyl-guanidines,corresponding ethers and thioethers and processes for their preparation |
| US3582315A (en) * | 1968-03-22 | 1971-06-01 | Lilly Co Eli | Methods and compositions for inhibiting plant growth |
| US3752812A (en) * | 1970-02-05 | 1973-08-14 | Pfizer | 2-trifluoromethylquinoxalinedi n oxides |
| US3928608A (en) * | 1972-03-14 | 1975-12-23 | Ici Ltd | Certain quinoxaline N-oxides used to combat fungi |
| DE2223894C3 (de) * | 1972-05-17 | 1981-07-23 | Hoechst Ag, 6000 Frankfurt | Herbizide Mittel auf Basis von Phenoxycarbonsäurederivaten |
| US4115102A (en) * | 1974-10-17 | 1978-09-19 | Ishihara Sangyo Kaisha, Ltd. | Pyridyl compound, herbicidal composition containing the same and method of use thereof |
| DE2640730C2 (de) * | 1976-09-10 | 1983-08-25 | Hoechst Ag, 6230 Frankfurt | Benzoxazolyloxy- und Benzothiazolyloxy-phenoxy-Verbindungen und diese enthaltende herbizide Mittel |
| DE2967486D1 (en) * | 1978-03-01 | 1985-08-29 | Ici Plc | Mixtures of herbicidal pyridyloxyphenoxypropanoic acid derivatives with other herbicides, and processes of killing unwanted plants therewith |
| US4391628A (en) * | 1981-02-16 | 1983-07-05 | Ciba-Geigy Corporation | 2-[4-(6-Haloquinoxalinyl-2-oxy)phenoxy]propionic acid esters |
-
1979
- 1979-02-22 JP JP54020164A patent/JPS6033389B2/ja not_active Expired
-
1980
- 1980-01-29 US US06/116,381 patent/US4629493A/en not_active Expired - Lifetime
- 1980-01-31 IL IL59281A patent/IL59281A/xx unknown
- 1980-01-31 ZA ZA00800574A patent/ZA80574B/xx unknown
- 1980-02-07 GB GB8004144A patent/GB2042539B/en not_active Expired
- 1980-02-08 DE DE3051251A patent/DE3051251C2/de not_active Expired - Lifetime
- 1980-02-08 DE DE19803004770 patent/DE3004770A1/de active Granted
- 1980-02-08 DE DE3051172A patent/DE3051172C2/de not_active Expired - Lifetime
- 1980-02-13 NL NLAANVRAGE8000888,A patent/NL185280C/xx not_active IP Right Cessation
- 1980-02-14 CH CH1207/80A patent/CH647510A5/de not_active IP Right Cessation
- 1980-02-18 CA CA000345903A patent/CA1306259C/en not_active Expired - Lifetime
- 1980-02-18 FR FR8003505A patent/FR2449683A1/fr active Granted
- 1980-02-19 CS CS801157A patent/CS226009B2/cs unknown
- 1980-02-20 ES ES488795A patent/ES488795A0/es active Granted
- 1980-02-20 AU AU55729/80A patent/AU533042B2/en not_active Expired
- 1980-02-20 EG EG101/80A patent/EG14184A/xx active
- 1980-02-20 BE BE0/199466A patent/BE881815A/fr not_active IP Right Cessation
- 1980-02-20 PL PL1980222116A patent/PL128652B1/pl unknown
- 1980-02-20 AT AT0093280A patent/AT365407B/de not_active IP Right Cessation
- 1980-02-20 DD DD80219165A patent/DD151038A5/de not_active IP Right Cessation
- 1980-02-21 SU SU802883702A patent/SU1452455A3/ru active
- 1980-02-21 AR AR280042A patent/AR226300A1/es active
- 1980-02-21 SE SE8001368A patent/SE447108B/sv not_active IP Right Cessation
- 1980-02-22 BR BR8001061A patent/BR8001061A/pt not_active IP Right Cessation
- 1980-02-22 IT IT20112/80A patent/IT1195260B/it active
-
1983
- 1983-04-13 CA CA000425818A patent/CA1304377C/en not_active Expired - Lifetime
- 1983-07-26 GB GB08320051A patent/GB2126580B/en not_active Expired
-
1989
- 1989-06-02 NL NL8901398A patent/NL8901398A/nl active Search and Examination
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1491274A (en) * | 1974-10-17 | 1977-11-09 | Ishihara Mining & Chemical Co | Substituted(pyridyl-2-oxy)phenoxy alkane carboxylic acid derivatives and their use as herbicides |
| DE2609461A1 (de) * | 1976-03-08 | 1977-09-22 | Hoechst Ag | Phenoxy-phenoxy-alkancarbonsaeurederivate |
| US4130431A (en) * | 1976-07-05 | 1978-12-19 | Kansai Paint Co., Ltd. | Metal surface treatment liquid and rust preventive paint |
| EP0000176A1 (de) * | 1977-06-29 | 1979-01-10 | Ciba-Geigy Ag | Pyridyloxy-phenoxy-alkancarbonsäurederivate, Verfahren zu deren Herstellung, und deren Verwendung als Herbizide oder als pflanzenwachstumsregulierende Mittel |
Non-Patent Citations (1)
| Title |
|---|
| J. Chem. Soc., Perkin I, 1974, S. 129-132 * |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3051172C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| DE2732846C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| DE69133039T2 (de) | Zwischenprodukte für herbizide Carboxamidderivate | |
| DD141403A5 (de) | Herbizide mittel | |
| DD249175A5 (de) | Insektizide mittel | |
| DE3941966A1 (de) | Halogenierte olefine, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel | |
| EP0118854B1 (de) | Chinoloncarbonsäure enthaltende bakterizide Mittel | |
| DE2652384A1 (de) | Neue herbizid wirksame, kernsubstituierte phenoxy-phenoxy-alkancarbonsaeurederivate und deren verwendung zur bekaempfung von ungraesern | |
| EP0125506A1 (de) | 5-(2,6-Dichlor-4-trifluormethyl-phenoxy)-2-nitrobenzaldehyd-diacetacylal | |
| DE69612611T2 (de) | Triazin-derivate | |
| CH630883A5 (en) | Process for the preparation of phenoxyalkanoic acid derivatives, and their use as herbicides | |
| DD209718A5 (de) | Schaedlingsbekaempfungsmittel | |
| EP0121727B1 (de) | Bakterizide Mittel auf Chinoloncarbonsäure-Basis | |
| EP0029542A2 (de) | Hydroxybutyl-imidazol-Derivate, Verfahren zu ihrer Herstellung, zu letzterer benötigte Zwischenprodukte sowie ihre Verwendung als Fungizide | |
| EP0068260A2 (de) | Substituierte Phenoxypropionate, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide | |
| EP0003297B1 (de) | Neue Phenoxy-alkyl-oxazoline, deren Herstellung, sie enthaltende herbizide Mittel und deren Verwendung | |
| DE2732442A1 (de) | Neue phenoxy-phenoxy-alkancarbonsaeurederivate | |
| DE3139457A1 (de) | Neue substituierte benzanilidether, verfahren zu ihrer herstellung, ihre verwendung als fungizide und zwischenprodukte hierfuer | |
| EP0161455A1 (de) | Beta-naphthylalkylamine | |
| DD254733A5 (de) | Verfahren zur herstellung von phenoxyalkanoltriazolverbindungen | |
| EP0254150A1 (de) | Decahydronapht-2-yl-alkylamine | |
| DE2855422A1 (de) | Insektizide phenylcyclopropancarbonsaeureester | |
| DE2533886A1 (de) | Spirolacton-derivate, verfahren zu deren herstellung und deren anwendung als fungicide | |
| DE2912052C2 (de) | Verfahren zur Herstellung von 2-[4-(2- Thienylcarbonyl)-phenyl]-propionsäure | |
| EP0170047B1 (de) | Verfahren zur Herstellung von Milchsäuresilylestern |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| Q172 | Divided out of (supplement): |
Ref country code: DE Ref document number: 3004770 |
|
| 8110 | Request for examination paragraph 44 | ||
| AC | Divided out of |
Ref country code: DE Ref document number: 3004770 Format of ref document f/p: P |
|
| D2 | Grant after examination | ||
| AC | Divided out of |
Ref country code: DE Ref document number: 3004770 Format of ref document f/p: P |
|
| 8364 | No opposition during term of opposition |