EA009557B1 - Синтетические соединения, пригодные в качестве агентов формирования клубеньков бобовых растений, и способы их получения - Google Patents
Синтетические соединения, пригодные в качестве агентов формирования клубеньков бобовых растений, и способы их получения Download PDFInfo
- Publication number
- EA009557B1 EA009557B1 EA200601260A EA200601260A EA009557B1 EA 009557 B1 EA009557 B1 EA 009557B1 EA 200601260 A EA200601260 A EA 200601260A EA 200601260 A EA200601260 A EA 200601260A EA 009557 B1 EA009557 B1 EA 009557B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- alkyl
- substituent selected
- fucosyl
- denote
- denotes
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 164
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- 238000002360 preparation method Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 14
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- 125000000217 alkyl group Chemical group 0.000 claims description 203
- 125000001424 substituent group Chemical group 0.000 claims description 169
- 229910052799 carbon Inorganic materials 0.000 claims description 165
- 229910052739 hydrogen Inorganic materials 0.000 claims description 161
- -1 methylfucosyl Chemical group 0.000 claims description 90
- 125000002446 fucosyl group Chemical group C1([C@@H](O)[C@H](O)[C@H](O)[C@@H](O1)C)* 0.000 claims description 88
- 125000004432 carbon atom Chemical group C* 0.000 claims description 80
- 229920006395 saturated elastomer Polymers 0.000 claims description 64
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 62
- 229910052757 nitrogen Inorganic materials 0.000 claims description 58
- 229910052717 sulfur Chemical group 0.000 claims description 57
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 56
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 56
- 125000005842 heteroatom Chemical group 0.000 claims description 56
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 52
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- 125000003118 aryl group Chemical group 0.000 claims description 31
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- 125000000089 arabinosyl group Chemical group C1([C@@H](O)[C@H](O)[C@H](O)CO1)* 0.000 claims description 28
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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 claims description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 12
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 12
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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)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Dentistry (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (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)
- Steroid Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Applications Claiming Priority (2)
| 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 |
| 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)
| Publication Number | Publication Date |
|---|---|
| EA200601260A1 EA200601260A1 (ru) | 2006-10-27 |
| EA009557B1 true EA009557B1 (ru) | 2008-02-28 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA200601260A EA009557B1 (ru) | 2003-12-30 | 2004-12-22 | Синтетические соединения, пригодные в качестве агентов формирования клубеньков бобовых растений, и способы их получения |
Country Status (25)
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|---|---|
| US (3) | US7619076B2 (https=) |
| EP (1) | EP1701967B1 (https=) |
| JP (1) | JP5031376B2 (https=) |
| KR (1) | KR101127785B1 (https=) |
| 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=) |
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Families Citing this family (66)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2348027B1 (en) | 2006-04-07 | 2013-10-23 | E. I. du Pont de Nemours and Company | 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 |
| RU2508631C2 (ru) | 2007-01-09 | 2014-03-10 | Новозаймс Байолоджиклз Холдинг А/С | Композиции на основе комбинации липо-хитоолигосахарида для усиления роста и урожайности растений |
| BRPI0817934B1 (pt) * | 2007-10-16 | 2017-03-21 | Merck Patent Ges Mit Beschränkter Haftung | composição e métodos para melhorar sinergicamente o rendimento de plantação compreendendo combinação de genisteína, daidzeína e lipo-quitooligossacarídeo de rhizobium leguminosarum " |
| WO2010049751A1 (en) | 2008-10-29 | 2010-05-06 | Institut National De La Recherche Agronomique | Lipochitooligosaccharides stimulating arbuscular mycorrhizal symbiosis |
| US9131685B2 (en) * | 2009-04-28 | 2015-09-15 | Bayer Cropscience Ag | Compositions comprising a strigolactone compound and a chito-oligosaccharide compound for enhanced plant growth and yield |
| BR112013022998A2 (pt) * | 2011-03-10 | 2018-07-03 | Bayer Ip Gmbh | método para aprimorar a germinação das sementes. |
| CN103648284B (zh) * | 2011-03-31 | 2016-09-21 | 诺维信生物股份有限公司 | 有竞争力且有效的大豆慢生根瘤菌菌株 |
| CA2847569C (en) | 2011-09-08 | 2020-05-19 | Novozymes Bioag A/S | Seed treatment methods and compositions comprising lipo-chitooligosaccharides |
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| CA2849901A1 (en) | 2011-09-23 | 2013-03-28 | Novozymes Bioag A/S | Chitooligosaccharides and methods for use in enhancing corn growth |
| EP2747568B1 (en) | 2011-09-23 | 2019-05-22 | Novozymes Bioag A/S | Combinations of lipo-chitooligosaccharides and methods for use in enhancing plant growth |
| CN105746517A (zh) | 2011-09-23 | 2016-07-13 | 诺维信生物农业公司 | 用于增强大豆生长的壳寡糖和方法 |
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| RU2646138C1 (ru) | 2011-12-16 | 2018-03-01 | Новозимс Биоаг А/С | Способ обработки семени растения |
| JP6456145B2 (ja) | 2012-01-21 | 2019-01-23 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | 有用な植物における細菌性有害微生物を防除するための宿主防御誘発物質の使用 |
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| 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 |
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| JP2016510073A (ja) | 2013-03-12 | 2016-04-04 | 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 | 有用植物において細菌性有害生物を防除するためのジチイン−テトラカルボキシイミドの使用 |
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| US11168085B2 (en) | 2014-01-24 | 2021-11-09 | Synaffix B.V. | Process for the cycloaddition of a hetero(aryl) 1,3-dipole compound with a (hetero)cycloalkyne |
| US10266502B2 (en) | 2014-01-24 | 2019-04-23 | Synaffix B.V. | Process for the cycloaddition of a halogenated 1,3-dipole compound with a (hetero)cycloalkyne |
| EP3097200A1 (en) * | 2014-01-24 | 2016-11-30 | SynAffix B.V. | Process for the attachment of a galnac moiety comprising a (hetero)aryl group to a glcnac moiety, and product obtained thereby |
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| US20170027167A1 (en) | 2014-03-05 | 2017-02-02 | Novozymes Bioag A/S | Formulations comprising polymeric xyloglucan as a carrier for agriculturally beneficial agents |
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| MX2018007932A (es) | 2015-12-28 | 2019-02-26 | Novozymes Bioag As | Composiciones de inoculante estables y metodos para producir las mismas. |
| CA3025912A1 (en) | 2016-05-31 | 2017-12-07 | Novozymes Bioag A/S | Stable liquid inoculant compositions and coated plant propagation materials comprising same |
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| BR112019012319A2 (pt) | 2016-12-20 | 2019-11-19 | Novozymes Bioag As | composição inoculante, métodos, material de propagação de planta revestido, e, kit. |
| CA3048994A1 (en) | 2017-01-03 | 2018-07-12 | Monsanto Technology Llc | Microbial compositions and methods |
| CA3048997A1 (en) | 2017-01-03 | 2018-07-12 | Monsanto Technology Llc | Microbial compositions and methods |
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| BR112019013816A2 (pt) | 2017-01-05 | 2020-01-21 | Novozymes Bioag As | cepa microbiana isolada, cultura de lysinibacillus sphaericus, composição inoculante, material de propagação de planta revestido, kit, e, métodos para tratar uma semente de planta e para aprimorar o rendimento da plantação |
| 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 |
| BR122023022721A2 (pt) | 2017-03-24 | 2023-12-26 | Novozymes Bioag A/S | Composição que compreende quantidades sinergicamente eficazes de yersinia entomophaga, ou um filtrado isento de células da mesma, e um inseticida químico; e método |
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| WO2019217255A1 (en) | 2018-05-07 | 2019-11-14 | Novozymes Bioag A/S | Microbacterium isolates and uses thereof |
| MX2021004792A (es) | 2018-11-01 | 2021-06-08 | Monsanto Technology Llc | Tratador de semillas. |
| WO2020263812A1 (en) | 2019-06-24 | 2020-12-30 | Auburn University | A bacillus strain and methods of its use for plant growth promotion |
| JP7513291B2 (ja) | 2019-06-24 | 2024-07-09 | 国立研究開発法人農業・食品産業技術総合研究機構 | エルウィニア属分離株およびその利用 |
| EP3818829A3 (en) | 2019-10-16 | 2021-07-21 | Monsanto Technology LLC | Granular nematicide compositions |
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| US12364266B2 (en) | 2019-11-20 | 2025-07-22 | Novozymes Bioag A/S | Pseudomonas isolates and uses thereof |
| CA3158954A1 (en) | 2019-11-22 | 2021-05-27 | Novozymes Bioag A/S | Paenibacillus isolates and uses thereof |
| 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 |
|---|---|---|---|---|
| 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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-
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Non-Patent Citations (3)
| Title |
|---|
| CARDENAS, LUIS ET AL.: "Isolation, chemical structures and biological activity of the lipo-chitin oligosaccharide nodulation signals from Rhizobium etli", PLANT MOLECULAR BIOLOGY, 29(3), 453-64 CODEN: PMBIDB; ISSN: 0167-4412, 1995, XP009035996 * |
| ROBINA I. ET AL.: "Synthesis and conformational analysis of a lipotetrasaccharide related to the nodulation factor of Rhizobium bacteria", TETRAHEDRON: ASYMMETRY, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 8, no. 8, 24 April 1997 (1997-04-24), pages 1207-1224, XP004059913, ISSN: 0957-4166 * |
| ROBINA, INMACULADA ET AL.: "Fatty acylamino-trisaccharides. Synthesis and some stereochemical properties", TETRAHEDRON, 52(32), 10771-10784 CODEN: TETRAB; ISSN: 0040-4020, 1996, XP002294810 * |
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