JP5031376B2 - マメ科植物の根粒形成因子として有用な合成化合物及びその調製方法 - Google Patents
マメ科植物の根粒形成因子として有用な合成化合物及びその調製方法 Download PDFInfo
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- JP5031376B2 JP5031376B2 JP2006546134A JP2006546134A JP5031376B2 JP 5031376 B2 JP5031376 B2 JP 5031376B2 JP 2006546134 A JP2006546134 A JP 2006546134A JP 2006546134 A JP2006546134 A JP 2006546134A JP 5031376 B2 JP5031376 B2 JP 5031376B2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pretreatment Of Seeds And Plants (AREA)
- Fertilizers (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Steroid Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0315543A FR2864538B1 (fr) | 2003-12-30 | 2003-12-30 | Composes synthetiques utiles comme facteurs de nodulation des plantes legumineuses et procedes de preparation de tels composes |
| FR0315543 | 2003-12-30 | ||
| PCT/EP2004/014909 WO2005063784A1 (en) | 2003-12-30 | 2004-12-22 | Synthetic compounds useful as nodulation agents of leguminous plants and preparation processes thereof |
Publications (2)
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| JP2007517002A JP2007517002A (ja) | 2007-06-28 |
| JP5031376B2 true JP5031376B2 (ja) | 2012-09-19 |
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| JP2006546134A Expired - Fee Related JP5031376B2 (ja) | 2003-12-30 | 2004-12-22 | マメ科植物の根粒形成因子として有用な合成化合物及びその調製方法 |
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| EP (1) | EP1701967B1 (https=) |
| JP (1) | JP5031376B2 (https=) |
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| CN (1) | CN100549020C (https=) |
| AP (1) | AP2328A (https=) |
| AR (2) | AR047174A1 (https=) |
| AT (1) | ATE504593T1 (https=) |
| AU (1) | AU2004309089B2 (https=) |
| BR (1) | BRPI0417892B1 (https=) |
| CA (1) | CA2540074C (https=) |
| DE (1) | DE602004032175D1 (https=) |
| EA (1) | EA009557B1 (https=) |
| ES (1) | ES2364556T3 (https=) |
| FR (1) | FR2864538B1 (https=) |
| IL (1) | IL175658A (https=) |
| IN (1) | IN2006DE01668A (https=) |
| MA (1) | MA28296A1 (https=) |
| MX (1) | MX258070B (https=) |
| NZ (1) | NZ546188A (https=) |
| OA (1) | OA13354A (https=) |
| PL (1) | PL1701967T3 (https=) |
| PT (1) | PT1701967E (https=) |
| WO (1) | WO2005063784A1 (https=) |
| ZA (1) | ZA200605258B (https=) |
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| CA2644172A1 (en) | 2006-04-07 | 2007-10-18 | E.I. Du Pont De Nemours And Company | Processes for chemical synthesis of lipochitooligosaccharides |
| TWI421030B (zh) * | 2006-12-12 | 2014-01-01 | Bayer Cropscience Ag | 包括用作豆科植物生結瘤劑（ｎｏｄｕｌａｔｉｏｎ ａｇｅｎｔ）之合成化合物及殺真菌劑化合物之農藥組合物 |
| TWI462698B (zh) * | 2006-12-12 | 2014-12-01 | Bayer Cropscience Ag | 包括作為豆科植物生結瘤劑（ｎｏｄｕｌａｔｉｏｎ ａｇｅｎｔ）之合成化合物及殺昆蟲劑化合物之農藥組合物 |
| US8357631B2 (en) | 2007-01-09 | 2013-01-22 | Novozymes Bioag, Inc. | Lipo-chitooligosaccharide combination compositions for enhanced plant growth and yield |
| WO2009049747A2 (en) * | 2007-10-16 | 2009-04-23 | Merck Patent Gmbh | Lipo-chitooligosaccharide and flavonoid combination for enhanced plant growth and yield |
| WO2010049751A1 (en) | 2008-10-29 | 2010-05-06 | Institut National De La Recherche Agronomique | Lipochitooligosaccharides stimulating arbuscular mycorrhizal symbiosis |
| WO2010125065A2 (en) * | 2009-04-28 | 2010-11-04 | Bayer Cropscience Ag | Compositions comprising a strigolactone compound and a chito-oligosaccharide compound for enhanced plant growth and yield |
| EP2683239A1 (en) * | 2011-03-10 | 2014-01-15 | Bayer Intellectual Property GmbH | Use of lipochito-oligosaccharide compounds for safeguarding seed safety of treated seeds |
| WO2012135704A1 (en) | 2011-03-31 | 2012-10-04 | Novozymes Biologicials, Inc | Competitive and effective bradyrhizobium japonicum strains |
| AR090026A1 (es) | 2011-09-08 | 2014-10-15 | Novozymes Bioag As | Metodos y composiciones para tratamiento de semillas |
| ES2970761T3 (es) | 2011-09-14 | 2024-05-30 | Novozymes Bioag As | Uso de lipoquitooligosacáridos y/o quitooligosacáridos en combinación con microorganismos solubilizadores de fosfato para potenciar el crecimiento de las plantas |
| RU2564844C1 (ru) | 2011-09-23 | 2015-10-10 | Новозимс Биоаг А/С | Хитоолигосахариды и способы их применения для усиления роста растений |
| UA123664C2 (uk) | 2011-09-23 | 2021-05-12 | Новозаймс Біоаг А/С | Комбінації ліпохітоолігосахаридів і способи для застосування при стимулюванні росту рослин |
| CA2849899A1 (en) | 2011-09-23 | 2013-03-28 | Novozymes Bioag A/S | Chitooligosaccharides and methods for use in enhancing soybean growth |
| AU2012312006B2 (en) | 2011-09-23 | 2015-10-29 | Novozymes Bioag A/S | Chitooligosaccharides and methods for use in enhancing corn growth |
| RU2646138C1 (ru) | 2011-12-16 | 2018-03-01 | Новозимс Биоаг А/С | Способ обработки семени растения |
| WO2013107785A1 (en) | 2012-01-21 | 2013-07-25 | Bayer Intellectual Property Gmbh | Use of host defense inducers for controlling bacterial harmful organisms in useful plants |
| WO2013139949A1 (en) | 2012-03-23 | 2013-09-26 | Bayer Intellectual Property Gmbh | Compositions comprising a strigolactame compound for enhanced plant growth and yield |
| AR091104A1 (es) | 2012-05-22 | 2015-01-14 | Bayer Cropscience Ag | Combinaciones de compuestos activos que comprenden un derivado lipo-quitooligosacarido y un compuesto nematicida, insecticida o fungicida |
| FR2991682A1 (fr) * | 2012-06-12 | 2013-12-13 | Centre Nat Rech Scient | Procedes de preparation de lipochito-oligosaccharides et de leurs precurseurs |
| FR2994793A1 (fr) | 2012-08-30 | 2014-03-07 | Agronomique Inst Nat Rech | Utilisation d'un recepteur kinase a motifs lysm pour ameliorer la reponse des plantes aux lipochitooligosaccharides. |
| WO2014049546A2 (en) | 2012-09-27 | 2014-04-03 | Institut National De La Recherche Agronomique | Compositions and methods for enhancing plant growth and development |
| US9365464B2 (en) | 2012-11-16 | 2016-06-14 | Novozymes Bioag A/S | Microbial strains, compositions, and methods for increasing available phosphate for plants |
| CA2904328A1 (en) * | 2013-03-06 | 2014-09-12 | E. I. Du Pont De Nemours And Company | Synthetic lipochitooligosaccharide analogs for enhancing plant performance |
| US20160024108A1 (en) | 2013-03-12 | 2016-01-28 | Bayer Cropscience Aktiengesellschaft | Use of dithiine-tetracarboximides for controlling bacterial harmful organisms in useful plants |
| WO2014160827A1 (en) | 2013-03-28 | 2014-10-02 | Novozymes Bioag A/S | Compositions and methods for enhancing microbial stability |
| WO2015048627A1 (en) | 2013-09-30 | 2015-04-02 | Bayer Cropscience Lp, A Delaware Limited Partnership | Streptomyces microflavus strains and methods of their use for the treatment and prevention of citrus greening disease |
| UA119331C2 (uk) | 2013-11-08 | 2019-06-10 | Новозімес Біоаґ А/С | Композиції та способи для обробки від шкідників |
| WO2015077278A1 (en) | 2013-11-20 | 2015-05-28 | Novozymes Bioag A/S | Compositions and methods comprising chromobacterium for controlling plant nematode pests and plant insect pests |
| CN106660967A (zh) | 2014-01-24 | 2017-05-10 | 西纳福克斯股份有限公司 | (杂)芳基1，3‑偶极化合物与(杂)环炔的环加成方法 |
| WO2015112013A1 (en) * | 2014-01-24 | 2015-07-30 | Synaffix B.V. | Process for the attachment of a galnac moiety comprising a (hetero)aryl group to a glcnac moiety, and product obtained thereby |
| WO2015112016A1 (en) | 2014-01-24 | 2015-07-30 | Synaffix B.V. | Process for the cycloaddition of a halogenated 1,3-dipole compound with a (hetero)cycloalkyne |
| WO2015134256A1 (en) | 2014-02-28 | 2015-09-11 | E. I. Du Pont De Nemours And Company | Combinatorial libraries |
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| US11472981B2 (en) | 2015-09-11 | 2022-10-18 | Novozymes Bioag A/S | Stable inoculant compositions and methods for producing same |
| JP2019503714A (ja) | 2015-12-28 | 2019-02-14 | ノボザイムス バイオアーゲー アクティーゼルスカブ | 安定した接種組成物およびその製造方法 |
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| US11089776B2 (en) | 2017-02-28 | 2021-08-17 | Monsanto Technology Llc | Containerized liquid formulations |
| WO2018159393A1 (ja) * | 2017-03-01 | 2018-09-07 | 花王株式会社 | マメ科植物生育促進剤 |
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| EP3818829A3 (en) | 2019-10-16 | 2021-07-21 | Monsanto Technology LLC | Granular nematicide compositions |
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| WO2021101937A1 (en) | 2019-11-20 | 2021-05-27 | Novozymes Bioag A/S | Pseudomonas isolates and uses thereof |
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| CN114075254B (zh) * | 2020-08-21 | 2024-01-30 | 佛山市海力盈生物科技有限公司 | 一类壳寡糖衍生物杀线剂及其制备方法和应用 |
| WO2022125639A1 (en) | 2020-12-08 | 2022-06-16 | Monsanto Technology Llc | Modified plant-associated bacteria and methods of their use |
| CN119859078B (zh) * | 2025-01-23 | 2025-07-18 | 江西瑞博特生物科技有限公司 | 一种氨基酸硒叶面肥及其制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| FR2660658A1 (fr) * | 1990-04-06 | 1991-10-11 | Centre Nat Rech Scient | Substances de structure oligosaccharidique propres a jouer le role de signaux symbiotiques plantes-specifiques, leurs procedes de production et leurs applications. |
| US5175149A (en) * | 1991-10-04 | 1992-12-29 | The University Of Tennessee Research Corporation | Pentasaccharide phytohormones and methods for their use |
| FR2692896B1 (fr) * | 1992-06-29 | 1994-09-09 | Institut Rech Agronomique | Signaux de nodulation de rhizobiaceae à large spectre d'hôte. |
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