SK282475B6 - Spôsob potlačovania rastu nežiaducich rastlín, 2,6-substituované pyridíny, spôsoby ich výroby, použitie a herbicídny prostriedok na ich báze - Google Patents
Spôsob potlačovania rastu nežiaducich rastlín, 2,6-substituované pyridíny, spôsoby ich výroby, použitie a herbicídny prostriedok na ich báze Download PDFInfo
- Publication number
- SK282475B6 SK282475B6 SK1184-95A SK118495A SK282475B6 SK 282475 B6 SK282475 B6 SK 282475B6 SK 118495 A SK118495 A SK 118495A SK 282475 B6 SK282475 B6 SK 282475B6
- Authority
- SK
- Slovakia
- Prior art keywords
- yloxy
- ethyl
- yioxy
- methyl
- chloropyrid
- Prior art date
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- 150000003222 pyridines Chemical class 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 title claims description 27
- 230000002363 herbicidal effect Effects 0.000 title claims description 21
- 206010053759 Growth retardation Diseases 0.000 title 1
- -1 2-chloropyrid-4-yl Chemical group 0.000 claims description 60
- 150000001875 compounds Chemical class 0.000 claims description 47
- 239000000203 mixture Substances 0.000 claims description 36
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 36
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 229910052751 metal Inorganic materials 0.000 claims description 12
- 239000002184 metal Substances 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- 150000003573 thiols Chemical class 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 230000012010 growth Effects 0.000 claims description 9
- 125000001188 haloalkyl group Chemical group 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000004094 surface-active agent Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- ZDDBCRDVANWNLT-UHFFFAOYSA-N 2,6-bis[(6-bromopyridin-2-yl)sulfanyl]pyridine Chemical compound BrC1=CC=CC(SC=2N=C(SC=3N=C(Br)C=CC=3)C=CC=2)=N1 ZDDBCRDVANWNLT-UHFFFAOYSA-N 0.000 claims description 2
- PXUNAIDRXQGFII-UHFFFAOYSA-N 2-(6-methoxypyridin-2-yl)sulfanyl-1,3-thiazole Chemical compound COC1=CC=CC(SC=2SC=CN=2)=N1 PXUNAIDRXQGFII-UHFFFAOYSA-N 0.000 claims description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
- AHDUXCOSCVKGQJ-UHFFFAOYSA-N 2-methoxy-6-(1h-1,2,4-triazol-5-ylsulfanyl)pyridine Chemical compound COC1=CC=CC(SC=2NN=CN=2)=N1 AHDUXCOSCVKGQJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 5
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 2
- VPUAYOJTHRDUTK-UHFFFAOYSA-N 1-ethylpyrrole Chemical compound CCN1C=CC=C1 VPUAYOJTHRDUTK-UHFFFAOYSA-N 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 230000008635 plant growth Effects 0.000 claims 1
- 239000003495 polar organic solvent Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- DRTZAIDVOGUYSP-UHFFFAOYSA-N pyridin-1-ium;chloride;hydrochloride Chemical compound Cl.Cl.C1=CC=NC=C1 DRTZAIDVOGUYSP-UHFFFAOYSA-N 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 239000004009 herbicide Substances 0.000 abstract description 3
- 239000003921 oil Substances 0.000 description 61
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 28
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 22
- 239000002904 solvent Substances 0.000 description 18
- 238000012360 testing method Methods 0.000 description 18
- 239000000243 solution Substances 0.000 description 15
- 241000196324 Embryophyta Species 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 239000002689 soil Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 11
- 239000000741 silica gel Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 238000003818 flash chromatography Methods 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 239000000969 carrier Substances 0.000 description 8
- 239000000284 extract Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
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- 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 5
- 239000004480 active ingredient Substances 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 150000002367 halogens Chemical group 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- OHBIPNNTWKNAGC-UHFFFAOYSA-N 2,6-dibromo-4-methylpyridine Chemical compound CC1=CC(Br)=NC(Br)=C1 OHBIPNNTWKNAGC-UHFFFAOYSA-N 0.000 description 3
- FEYDZHNIIMENOB-UHFFFAOYSA-N 2,6-dibromopyridine Chemical compound BrC1=CC=CC(Br)=N1 FEYDZHNIIMENOB-UHFFFAOYSA-N 0.000 description 3
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
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- 238000004458 analytical method Methods 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
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- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
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- VBEHFOMFHUQAOW-UHFFFAOYSA-N 2-chloro-1h-pyridin-4-one Chemical compound OC1=CC=NC(Cl)=C1 VBEHFOMFHUQAOW-UHFFFAOYSA-N 0.000 description 2
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- ABYCTYJDRLQBMT-UHFFFAOYSA-N 6-bromo-4-methylpyridin-2-amine Chemical compound CC1=CC(N)=NC(Br)=C1 ABYCTYJDRLQBMT-UHFFFAOYSA-N 0.000 description 2
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- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
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- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
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- 241000894007 species Species 0.000 description 1
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- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
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- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical class OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/69—Two or more oxygen atoms
-
- 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
-
- 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
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
-
- 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
- C07D401/14—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 three or more hetero rings
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)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP93105006 | 1993-03-26 | ||
| PCT/EP1994/000969 WO1994022833A1 (en) | 1993-03-26 | 1994-03-25 | Herbicidal heterocyclic-substituted pyridines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK118495A3 SK118495A3 (en) | 1996-06-05 |
| SK282475B6 true SK282475B6 (sk) | 2002-02-05 |
Family
ID=8212745
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1184-95A SK282475B6 (sk) | 1993-03-26 | 1994-03-25 | Spôsob potlačovania rastu nežiaducich rastlín, 2,6-substituované pyridíny, spôsoby ich výroby, použitie a herbicídny prostriedok na ich báze |
Country Status (23)
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1168718C (zh) * | 1995-06-28 | 2004-09-29 | 辛甄塔有限公司 | 2-(6-取代吡啶-2-基氧甲基)苯乙酸酯的制备方法 |
| US5710106A (en) * | 1996-02-22 | 1998-01-20 | American Cyanamid Company | Substituted pyridine herbicidal agents |
| US5677303A (en) * | 1996-06-20 | 1997-10-14 | American Cyanamid Company | Enolethers and their use as a fungicide |
| ATE243208T1 (de) * | 1996-07-30 | 2003-07-15 | Basf Ag | Trisubstitierte pyridinverbindungen zur anwendung als herbizide |
| ES2185041T3 (es) * | 1996-07-30 | 2003-04-16 | Basf Ag | Mezclas herbicidas. |
| ATE323696T1 (de) * | 1996-07-30 | 2006-05-15 | Herbizid wirsame substituierte pyridin-derivate | |
| US5977026A (en) * | 1996-07-30 | 1999-11-02 | American Cyanamid | Herbicidal mixtures |
| US5922738A (en) * | 1996-07-30 | 1999-07-13 | American Cyanamid Company | Heteroarylpyridine herbicides |
| US5981437A (en) * | 1996-07-30 | 1999-11-09 | American Cyanamid Company | Herbicidal substituted pyridine compounds |
| GB2317384B (en) * | 1996-09-19 | 2000-05-17 | American Cyanamid Co | Heteroarylpyridine herbicides |
| US5851952A (en) * | 1997-11-07 | 1998-12-22 | American Cyanamid Company | Herbicidal thienyloxyazines |
| EP1028959B1 (en) * | 1997-11-07 | 2007-06-27 | Basf Aktiengesellschaft | Herbicidal furanyl- and thienyloxyazines |
| US6121202A (en) * | 1997-11-07 | 2000-09-19 | American Cyanamid Company | Thienyloxypyridines and-pyrimidines useful as herbicidal agents |
| US5985796A (en) * | 1998-01-22 | 1999-11-16 | American Cyanamid Company | Herbicidal mixtures |
| CA2270843A1 (en) * | 1998-05-05 | 1999-11-05 | American Cyanamid Company | Herbicidal pyridine compounds |
| US6130188A (en) | 1998-05-05 | 2000-10-10 | American Cyanamid Company | Herbicidal pyridine compounds |
| EP0955292A1 (en) * | 1998-05-05 | 1999-11-10 | American Cyanamid Company | Herbicidal 2-(cycloalk(en)yloxy)-6-(hetero)aryloxy(thio)pyridines |
| JP2003514814A (ja) * | 1999-11-12 | 2003-04-22 | ビーエーエスエフ アクチェンゲゼルシャフト | 除草剤２−アリールオキシ−６−フルオロアルキルチオアルキル（アルケニル）オキシ−ピリジン |
| US6534447B1 (en) | 1999-11-12 | 2003-03-18 | Basf Aktiengesellschaft | Herbicidal pyridine compounds |
| CA2326020A1 (en) * | 1999-11-17 | 2001-05-17 | Basf Corporation | Herbicidal 2-aryloxy-4-methyl-6-pyrazol-1-yl-pyridines |
| EP1351571A2 (de) * | 1999-11-17 | 2003-10-15 | Bayer CropScience AG | Selektive herbizide auf basis von 2,6-disubstituierten pyridin-derivaten |
| US6448204B1 (en) | 1999-11-17 | 2002-09-10 | Basf Aktiengesellschaft | Herbicidal 2-aryloxy-4-methyl-6-pyrazol-1-yl-pyridines |
| US6528456B2 (en) | 1999-12-08 | 2003-03-04 | Basf Aktiengesellschaft | Herbicidal 2-pyrazolyl-6-aryloxypyri(mi)dines |
| EP1427719B1 (de) * | 2001-09-07 | 2005-11-02 | Basf Aktiengesellschaft | 4-alkylsubstituierte thienyloxy-pyrididne als herbizide |
| KR100641908B1 (ko) * | 2002-05-02 | 2006-11-02 | 주식회사 엘지생명과학 | 피리딘 유도체, 그의 제조방법, 및 제초제 중간체로서의용도 |
| DE102005014638A1 (de) * | 2005-03-31 | 2006-10-05 | Bayer Cropscience Gmbh | Substituierte Pyrazolyloxyphenylderivate als Herbizide |
| TWI471095B (zh) * | 2009-12-21 | 2015-02-01 | Nippon Soda Co | 環胺化合物及殺蟎劑 |
| AR081721A1 (es) | 2010-02-25 | 2012-10-17 | Nippon Soda Co | Compuesto de amina ciclica y acaricida |
| JP6303250B2 (ja) | 2012-12-21 | 2018-04-04 | 石原産業株式会社 | 有害生物防除剤 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3535328A (en) * | 1967-09-01 | 1970-10-20 | Exxon Research Engineering Co | Certain substituted aminothioethoxy pyridines |
| US3687959A (en) * | 1970-05-28 | 1972-08-29 | Exxon Research Engineering Co | Alkaryl-alkoxy, aryl-amido derivatives of pyridine |
| DK154074C (da) * | 1974-10-17 | 1989-02-27 | Ishihara Sangyo Kaisha | Alfa-(4-(5 eller 3,5 substitueret pyridyl-2-oxy)-phenoxy)-alkan-carboxylsyrer eller derivater deraf til anvendelse som herbicider, herbicidt middel samt fremgangsmaader til bekaempelse af ukrudt |
| CH620339A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1976-03-05 | 1980-11-28 | Ciba Geigy Ag | |
| DE2711655A1 (de) * | 1977-03-17 | 1978-09-21 | Basf Ag | Pyridinyl-aminoalkylaether |
| DE2862492D1 (en) * | 1977-08-12 | 1988-09-01 | Ici Plc | Herbicidal halogenomethyl--pyridyloxy-phenoxy-alkanecarboxylic acids and derivatives, and processes of controlling unwanted plants therewith |
| US4325729A (en) * | 1977-12-13 | 1982-04-20 | Ciba-Geigy Corporation | Herbicidal and plant growth regulating pyridyloxy-phenoxy-propionic acid derivatives |
| EP0003313B1 (de) * | 1978-01-27 | 1981-01-07 | Ciba-Geigy Ag | Neue Pyridyloxy-phenoxy-alpha-propionsäure-aminoalkyl-ester mit herbizider Wirkung,ihre Herstellung, sie enthaltende Mittel und deren Verwendung |
| JPS55139361A (en) * | 1979-04-19 | 1980-10-31 | Ishihara Sangyo Kaisha Ltd | Preparation of 4-(pyridyl-2-oxy)phenoxyalkane-carboxylic acid or its derivative |
| DE2949728A1 (de) * | 1979-12-11 | 1981-06-19 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von optisch aktiven 2-phenoxypropionsaeuren |
| IL64220A (en) * | 1980-11-21 | 1985-06-30 | May & Baker Ltd | Nicotinamide derivatives,their preparation and their use as herbicides |
| US4493730A (en) * | 1982-09-10 | 1985-01-15 | Ishihara Sangyo Kaisha, Ltd. | Phenoxypyridine useful as a herbicide |
| CA1215067A (en) * | 1982-10-18 | 1986-12-09 | Sudarshan K. Malhotra | 2-(6-phenoxy-3-nitro-2-pyridinoxy)-propionate compounds |
| EP0180188B1 (en) * | 1984-10-30 | 1992-04-15 | Otsuka Pharmaceutical Co., Ltd. | A composition for increasing the anti-cancer activity of an anti-cancer compound |
| JP2531952B2 (ja) * | 1987-04-06 | 1996-09-04 | 大塚製薬株式会社 | フオスホリラ−ゼ阻害剤 |
| US5185025A (en) * | 1988-11-21 | 1993-02-09 | Monsanto Company | Substituted pyrazoles and their use as herbicides |
| TW231258B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1992-05-27 | 1994-10-01 | Shell Internat Res Schappej B V |
-
1994
- 1994-03-24 IL IL10910494A patent/IL109104A/en active IP Right Grant
- 1994-03-25 WO PCT/EP1994/000969 patent/WO1994022833A1/en not_active Application Discontinuation
- 1994-03-25 ES ES94913064T patent/ES2111925T3/es not_active Expired - Lifetime
- 1994-03-25 MD MD96-0282A patent/MD1761B2/ro not_active Application Discontinuation
- 1994-03-25 AU AU65365/94A patent/AU696016B2/en not_active Ceased
- 1994-03-25 ZA ZA942126A patent/ZA942126B/xx unknown
- 1994-03-25 HU HU9501921A patent/HU217518B/hu not_active IP Right Cessation
- 1994-03-25 JP JP6521658A patent/JPH08508277A/ja active Pending
- 1994-03-25 CN CN94192038A patent/CN1083433C/zh not_active Expired - Fee Related
- 1994-03-25 EP EP94913064A patent/EP0690846B1/en not_active Expired - Lifetime
- 1994-03-25 UA UA95094238A patent/UA58478C2/uk unknown
- 1994-03-25 AT AT94913064T patent/ATE161831T1/de not_active IP Right Cessation
- 1994-03-25 TJ TJ96000356A patent/TJ247B/xx unknown
- 1994-03-25 CZ CZ952483A patent/CZ248395A3/cs unknown
- 1994-03-25 DK DK94913064.5T patent/DK0690846T3/da active
- 1994-03-25 DE DE69407770T patent/DE69407770T2/de not_active Expired - Fee Related
- 1994-03-25 BR BR9405910A patent/BR9405910A/pt not_active IP Right Cessation
- 1994-03-25 KR KR1019950704084A patent/KR100316679B1/ko not_active Expired - Fee Related
- 1994-03-25 RU RU95117980A patent/RU2140739C1/ru not_active IP Right Cessation
- 1994-03-25 US US08/525,690 patent/US5840654A/en not_active Expired - Lifetime
- 1994-03-25 SK SK1184-95A patent/SK282475B6/sk unknown
- 1994-03-30 TW TW083102793A patent/TW261513B/zh active
-
1998
- 1998-02-20 GR GR980400365T patent/GR3026187T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0690846A1 (en) | 1996-01-10 |
| HUT73165A (en) | 1996-06-28 |
| CZ248395A3 (en) | 1996-03-13 |
| US5840654A (en) | 1998-11-24 |
| DE69407770D1 (de) | 1998-02-12 |
| UA58478C2 (uk) | 2003-08-15 |
| TJ247B (en) | 1999-12-23 |
| ZA942126B (en) | 1994-11-10 |
| RU2140739C1 (ru) | 1999-11-10 |
| DK0690846T3 (da) | 1998-03-16 |
| IL109104A0 (en) | 1994-06-24 |
| ES2111925T3 (es) | 1998-03-16 |
| IL109104A (en) | 1998-08-16 |
| CN1122596A (zh) | 1996-05-15 |
| KR100316679B1 (ko) | 2002-05-30 |
| MD960282A (en) | 1999-01-31 |
| HU217518B (hu) | 2000-02-28 |
| AU6536594A (en) | 1994-10-24 |
| GR3026187T3 (en) | 1998-05-29 |
| TW261513B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1995-11-01 |
| SK118495A3 (en) | 1996-06-05 |
| MD1761B2 (ro) | 2001-10-31 |
| AU696016B2 (en) | 1998-08-27 |
| BR9405910A (pt) | 1995-12-26 |
| CN1083433C (zh) | 2002-04-24 |
| KR960701018A (ko) | 1996-02-24 |
| DE69407770T2 (de) | 1998-04-16 |
| EP0690846B1 (en) | 1998-01-07 |
| HU9501921D0 (en) | 1995-09-28 |
| ATE161831T1 (de) | 1998-01-15 |
| JPH08508277A (ja) | 1996-09-03 |
| WO1994022833A1 (en) | 1994-10-13 |
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