AU2001286294B2 - Herbicidal 5-benzyloxymethyl-1,2-isoxazoline derivatives - Google Patents
Herbicidal 5-benzyloxymethyl-1,2-isoxazoline derivatives Download PDFInfo
- Publication number
- AU2001286294B2 AU2001286294B2 AU2001286294A AU2001286294A AU2001286294B2 AU 2001286294 B2 AU2001286294 B2 AU 2001286294B2 AU 2001286294 A AU2001286294 A AU 2001286294A AU 2001286294 A AU2001286294 A AU 2001286294A AU 2001286294 B2 AU2001286294 B2 AU 2001286294B2
- Authority
- AU
- Australia
- Prior art keywords
- isoxazoline
- methyl
- oxymethyl
- fluorobenzyl
- difluorobenzyl
- 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.)
- Ceased
Links
- WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical class C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 title claims description 85
- 230000002363 herbicidal effect Effects 0.000 title claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 62
- -1 sodium alkoxide Chemical class 0.000 claims description 32
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- 239000000203 mixture Substances 0.000 claims description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 19
- 235000007164 Oryza sativa Nutrition 0.000 claims description 19
- 241000196324 Embryophyta Species 0.000 claims description 16
- 235000009566 rice Nutrition 0.000 claims description 16
- 239000004009 herbicide Substances 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims description 9
- 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
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- 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
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- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
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- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 claims description 6
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 4
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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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR2000-52917 | 2000-09-07 | ||
| 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 (2)
| Publication Number | Publication Date |
|---|---|
| AU2001286294A1 AU2001286294A1 (en) | 2002-06-13 |
| AU2001286294B2 true AU2001286294B2 (en) | 2004-04-08 |
Family
ID=19687824
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2001286294A Ceased AU2001286294B2 (en) | 2000-09-07 | 2001-09-05 | Herbicidal 5-benzyloxymethyl-1,2-isoxazoline derivatives |
| AU8629401A Pending AU8629401A (en) | 2000-09-07 | 2001-09-05 | Herbicidal 5-benzyloxymethyl-1,2-isoxazoline derivatives |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU8629401A Pending AU8629401A (en) | 2000-09-07 | 2001-09-05 | Herbicidal 5-benzyloxymethyl-1,2-isoxazoline derivatives |
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) |
Families Citing this family (16)
| 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 |
| CA2848695A1 (en) | 2011-09-13 | 2013-03-21 | Monsanto Technology Llc | Methods and composition for weed control comprising inhibiting ppg oxidase |
| WO2013040049A1 (en) | 2011-09-13 | 2013-03-21 | Monsanto Technology Llc | Methods and compositions for weed control |
| CN103958539B (zh) | 2011-09-13 | 2019-12-17 | 孟山都技术公司 | 用于杂草控制的方法和组合物 |
| 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 |
| US10568328B2 (en) | 2013-03-15 | 2020-02-25 | Monsanto Technology Llc | Methods and compositions for weed control |
| 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 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4983210A (en) * | 1988-03-23 | 1991-01-08 | Basf Aktiengesellschaft | Isoxazolines, their preparation and their use |
| US5262388A (en) * | 1991-05-20 | 1993-11-16 | Shell Research Limited | Herbicidal compounds |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4983210A (en) * | 1988-03-23 | 1991-01-08 | Basf Aktiengesellschaft | Isoxazolines, their preparation and their use |
| US5262388A (en) * | 1991-05-20 | 1993-11-16 | Shell Research Limited | Herbicidal compounds |
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 |
| JP3968012B2 (ja) | 2007-08-29 |
| US6838416B2 (en) | 2005-01-04 |
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| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |