JP3968012B2 - 除草活性を持った５−ベンジルオキシメチル−１，２−イソオキサゾリン誘導体 - Google Patents
除草活性を持った５−ベンジルオキシメチル−１，２−イソオキサゾリン誘導体 Download PDFInfo
- Publication number
- JP3968012B2 JP3968012B2 JP2002524317A JP2002524317A JP3968012B2 JP 3968012 B2 JP3968012 B2 JP 3968012B2 JP 2002524317 A JP2002524317 A JP 2002524317A JP 2002524317 A JP2002524317 A JP 2002524317A JP 3968012 B2 JP3968012 B2 JP 3968012B2
- Authority
- JP
- Japan
- Prior art keywords
- isoxazoline
- methyl
- oxymethyl
- difluorobenzyl
- fluorobenzyl
- 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
- WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical class C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 title claims description 94
- 230000002363 herbicidal effect Effects 0.000 title claims description 39
- -1 2-methylthiophen - 5-yl Chemical group 0.000 claims description 92
- 150000001875 compounds Chemical class 0.000 claims description 60
- 125000006508 2,6-difluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C(F)=C1[H])C([H])([H])* 0.000 claims description 31
- 240000007594 Oryza sativa Species 0.000 claims description 29
- 235000007164 Oryza sativa Nutrition 0.000 claims description 24
- 235000009566 rice Nutrition 0.000 claims description 23
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 21
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims description 19
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
- 241000196324 Embryophyta Species 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 244000058871 Echinochloa crus-galli Species 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 4
- 241001408202 Sagittaria pygmaea Species 0.000 claims description 4
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- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 4
- BYDRTKVGBRTTIT-UHFFFAOYSA-N 2-methylprop-2-en-1-ol Chemical compound CC(=C)CO BYDRTKVGBRTTIT-UHFFFAOYSA-N 0.000 claims description 3
- 235000003990 Monochoria hastata Nutrition 0.000 claims description 3
- 235000011999 Panicum crusgalli Nutrition 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 claims description 2
- 238000006736 Huisgen cycloaddition reaction Methods 0.000 claims description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- 150000004703 alkoxides Chemical class 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 claims description 2
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 claims description 2
- 229910000103 lithium hydride Inorganic materials 0.000 claims description 2
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 claims description 2
- 229910052987 metal hydride Inorganic materials 0.000 claims description 2
- 150000004681 metal hydrides Chemical class 0.000 claims description 2
- 125000005948 methanesulfonyloxy group Chemical group 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 claims description 2
- 241000169139 Monochoria Species 0.000 claims 2
- 150000007529 inorganic bases Chemical class 0.000 claims 1
- 238000002360 preparation method Methods 0.000 description 30
- VAUMDUIUEPIGHM-UHFFFAOYSA-N 5-Methyl-2-thiophenecarboxaldehyde Chemical compound CC1=CC=C(C=O)S1 VAUMDUIUEPIGHM-UHFFFAOYSA-N 0.000 description 24
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 20
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- 239000004009 herbicide Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- MJXRENZUAQXZGJ-UHFFFAOYSA-N 2-(chloromethyl)-1,3-difluorobenzene Chemical compound FC1=CC=CC(F)=C1CCl MJXRENZUAQXZGJ-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- XBDXMDVEZLOGMC-UHFFFAOYSA-N 1-(chloromethyl)-3-fluorobenzene Chemical compound FC1=CC=CC(CCl)=C1 XBDXMDVEZLOGMC-UHFFFAOYSA-N 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- BSQKBHXYEKVKMN-UHFFFAOYSA-N 3-methylthiophene-2-carbaldehyde Chemical compound CC=1C=CSC=1C=O BSQKBHXYEKVKMN-UHFFFAOYSA-N 0.000 description 4
- 229940126062 Compound A Drugs 0.000 description 4
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- MOBRMRJUKNQBMY-UHFFFAOYSA-N 1-(chloromethyl)-2-fluorobenzene Chemical compound FC1=CC=CC=C1CCl MOBRMRJUKNQBMY-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- NQWNJWZLWMCDOJ-UHFFFAOYSA-N 3,5-dimethylthiophene-2-carbaldehyde Chemical compound CC1=CC(C)=C(C=O)S1 NQWNJWZLWMCDOJ-UHFFFAOYSA-N 0.000 description 3
- GFBVUFQNHLUCPX-UHFFFAOYSA-N 5-bromothiophene-2-carbaldehyde Chemical compound BrC1=CC=C(C=O)S1 GFBVUFQNHLUCPX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- 231100000674 Phytotoxicity Toxicity 0.000 description 3
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- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- BCZHCWCOQDRYGS-UHFFFAOYSA-N 3-bromothiophene-2-carbaldehyde Chemical compound BrC=1C=CSC=1C=O BCZHCWCOQDRYGS-UHFFFAOYSA-N 0.000 description 2
- PJOJWMNHMJFFCR-UHFFFAOYSA-N 3-chlorothiophene-2-carbaldehyde Chemical compound ClC=1C=CSC=1C=O PJOJWMNHMJFFCR-UHFFFAOYSA-N 0.000 description 2
- KGJDTMQUUPIAEF-UHFFFAOYSA-N 3-methoxythiophene-2-carbaldehyde Chemical compound COC=1C=CSC=1C=O KGJDTMQUUPIAEF-UHFFFAOYSA-N 0.000 description 2
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- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
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- VSIIXMUUUJUKCM-UHFFFAOYSA-D pentacalcium;fluoride;triphosphate Chemical compound [F-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O VSIIXMUUUJUKCM-UHFFFAOYSA-D 0.000 description 1
- WQIJVELWNBSHCE-UHFFFAOYSA-N phenyl naphthalene-1-sulfonate Chemical compound C=1C=CC2=CC=CC=C2C=1S(=O)(=O)OC1=CC=CC=C1 WQIJVELWNBSHCE-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- DOKHEARVIDLSFF-UHFFFAOYSA-N prop-1-en-1-ol Chemical compound CC=CO DOKHEARVIDLSFF-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000004563 wettable powder Substances 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
Landscapes
- 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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2000-0052917A KR100392072B1 (ko) | 2000-09-07 | 2000-09-07 | 제초활성을 갖는 5-벤질옥시메틸-1,2-이속사졸린 유도체화합물 |
| PCT/KR2001/001500 WO2002019825A1 (en) | 2000-09-07 | 2001-09-05 | Herbicidal 5-benzyloxymethyl-1,2-isoxazoline derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004508309A JP2004508309A (ja) | 2004-03-18 |
| JP2004508309A5 JP2004508309A5 (enExample) | 2005-04-07 |
| JP3968012B2 true JP3968012B2 (ja) | 2007-08-29 |
Family
ID=19687824
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002524317A Expired - Lifetime JP3968012B2 (ja) | 2000-09-07 | 2001-09-05 | 除草活性を持った５−ベンジルオキシメチル−１，２−イソオキサゾリン誘導体 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6838416B2 (enExample) |
| JP (1) | JP3968012B2 (enExample) |
| KR (1) | KR100392072B1 (enExample) |
| CN (1) | CN1303081C (enExample) |
| AU (2) | AU2001286294B2 (enExample) |
| WO (1) | WO2002019825A1 (enExample) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014151255A1 (en) | 2013-03-15 | 2014-09-25 | Monsanto Technology Llc | Methods and compositions for weed control |
| EP3296402A2 (en) | 2011-09-13 | 2018-03-21 | Monsanto Technology LLC | Methods and compositions for weed control |
| EP3434779A1 (en) | 2011-09-13 | 2019-01-30 | Monsanto Technology LLC | Methods and compositions for weed control |
| EP3434780A1 (en) | 2011-09-13 | 2019-01-30 | Monsanto Technology LLC | Methods and compositions for weed control |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100392072B1 (ko) * | 2000-09-07 | 2003-07-22 | 한국화학연구원 | 제초활성을 갖는 5-벤질옥시메틸-1,2-이속사졸린 유도체화합물 |
| BR0309447A (pt) * | 2002-04-25 | 2005-02-09 | Basf Ag | Composto, agente, processos para a preparação dos mesmos, e para o combate do crescimento de plantas indesejadas, e, uso do composto |
| KR100814420B1 (ko) | 2007-06-22 | 2008-03-18 | (주)목우연구소 | 제초성 5-벤질옥시메틸-1,2-이속사졸린 유도체 화합물의용도 |
| US8445409B2 (en) * | 2007-06-22 | 2013-05-21 | Moghu Research Center Ltd. | Use of 5-benzyloxymethyl-1,2-isoxazoline derivatives as a herbicide |
| KR101093102B1 (ko) | 2011-10-04 | 2011-12-13 | (주)목우연구소 | 제초활성을 가지는 페닐이속사졸린계 화합물 및 이의 용도 |
| KR101201203B1 (ko) * | 2012-04-02 | 2012-11-15 | (주)목우연구소 | 고순도 메티오졸린의 공업적 제조방법 |
| JP6397820B2 (ja) * | 2012-09-25 | 2018-09-26 | バイエル・クロップサイエンス・アクチェンゲゼルシャフト | 除草活性と殺菌活性を示す３−ヘテロアリール−イソオキサゾリン−５−カルボキサミド類及び３−ヘテロアリール−イソオキサゾリン−５−チオアミド類 |
| KR101708208B1 (ko) | 2015-05-29 | 2017-02-21 | 한국화학연구원 | 광학활성 (s)-(4,5-다이하이드로이소옥사졸-5-일)카복실레이트 화합물과 이 화합물의 비대칭합성방법 |
| JP2021073168A (ja) * | 2018-03-08 | 2021-05-13 | 石原産業株式会社 | 除草組成物 |
| WO2019243101A1 (en) | 2018-06-20 | 2019-12-26 | Basf Se | Method for controlling herbicide resistant or tolerant weeds |
| KR20250020510A (ko) | 2022-06-10 | 2025-02-11 | 이시하라 산교 가부시끼가이샤 | 디플루오로부텐산아미드 화합물을 포함하는 제초 조성물 |
| KR20250097432A (ko) * | 2023-12-21 | 2025-06-30 | (주)목우연구소 | 1,3-다이플루오로-2-(((2-메틸알릴)옥시)메틸)벤젠을 중간체로 이용하는 고순도 메티오졸린의 제조방법 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3809765A1 (de) * | 1988-03-23 | 1989-10-05 | Basf Ag | Isoxazoline, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| GB9110858D0 (en) * | 1991-05-20 | 1991-07-10 | Shell Int Research | Herbicidal compounds |
| JPH09328477A (ja) * | 1996-06-10 | 1997-12-22 | Sankyo Co Ltd | 除草性イソオキサゾリン誘導体 |
| KR100392072B1 (ko) * | 2000-09-07 | 2003-07-22 | 한국화학연구원 | 제초활성을 갖는 5-벤질옥시메틸-1,2-이속사졸린 유도체화합물 |
-
2000
- 2000-09-07 KR KR10-2000-0052917A patent/KR100392072B1/ko not_active Expired - Lifetime
-
2001
- 2001-09-05 JP JP2002524317A patent/JP3968012B2/ja not_active Expired - Lifetime
- 2001-09-05 WO PCT/KR2001/001500 patent/WO2002019825A1/en not_active Ceased
- 2001-09-05 AU AU2001286294A patent/AU2001286294B2/en not_active Ceased
- 2001-09-05 AU AU8629401A patent/AU8629401A/xx active Pending
- 2001-09-05 US US10/363,808 patent/US6838416B2/en not_active Expired - Lifetime
- 2001-09-05 CN CNB01815140XA patent/CN1303081C/zh not_active Expired - Fee Related
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3296402A2 (en) | 2011-09-13 | 2018-03-21 | Monsanto Technology LLC | Methods and compositions for weed control |
| EP3434779A1 (en) | 2011-09-13 | 2019-01-30 | Monsanto Technology LLC | Methods and compositions for weed control |
| EP3434780A1 (en) | 2011-09-13 | 2019-01-30 | Monsanto Technology LLC | Methods and compositions for weed control |
| WO2014151255A1 (en) | 2013-03-15 | 2014-09-25 | Monsanto Technology Llc | Methods and compositions for weed control |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2002019825A1 (en) | 2002-03-14 |
| KR20020019750A (ko) | 2002-03-13 |
| JP2004508309A (ja) | 2004-03-18 |
| CN1303081C (zh) | 2007-03-07 |
| US20040023808A1 (en) | 2004-02-05 |
| AU8629401A (en) | 2002-03-22 |
| KR100392072B1 (ko) | 2003-07-22 |
| CN1452458A (zh) | 2003-10-29 |
| AU2001286294B2 (en) | 2004-04-08 |
| US6838416B2 (en) | 2005-01-04 |
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