WO2020102232A1 - Encapsulation of cyclohexanediones process and product - Google Patents
Encapsulation of cyclohexanediones process and product Download PDFInfo
- Publication number
- WO2020102232A1 WO2020102232A1 PCT/US2019/060981 US2019060981W WO2020102232A1 WO 2020102232 A1 WO2020102232 A1 WO 2020102232A1 US 2019060981 W US2019060981 W US 2019060981W WO 2020102232 A1 WO2020102232 A1 WO 2020102232A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- composition
- oil
- cyclohexanediones
- encapsulated
- crop
- 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
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
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen
- A01N35/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen containing a carbon-to-nitrogen double bond
-
- 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
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
- A01N25/10—Macromolecular compounds
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/22—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing ingredients stabilising the active ingredients
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/26—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests in coated particulate form
- A01N25/28—Microcapsules or nanocapsules
Definitions
- the field of art to which this invention generally pertains is products and methods of making products which are useful in fungicidal, insecticidal and herbicidal compositions.
- a composition particularly adapted for herbicidal use including one or more biopolymer containing micro-capsules containing one or more cyclohexanediones encapsulated therein, resulting in enhanced chemical stability and dispersibility of the encapsulated cyclohexanediones for such use.
- Additional embodiments include, the composition described above where the cyclohexanedione comprises Clethodim; the composition described above where the biopolymer comprises polysaccharide and/or cellulose; the composition described above where the polysaccharide comprises Inulin; the composition described above including one or more surfactants; the composition described above where the cyclohexanediones are present in the micro-capsules in an amount of 1% to 70% by weight; the composition described above made by complex coacervation; the composition described above where the composition optionally contains one or more natural gum, starch, protein, alcohol, water soluble polymer, and/or an oil; the composition described above where the alcohol comprises Sorbitol; the composition described above where the natural gum comprises Gum Arabic; the composition described above where the surfactant comprises one or more polyalkylene oxide block copolymers; a water dispersion containing the composition described above; and an oil dispersion containing the composition described above; the composition described above where the oil comprises vegetable oil
- composition described above where the polyoxyethylene sorbitan is a monolaurate, monostearate, tristearate, and/or trioleate.
- a method of controlling insects and/or weeds comprising applying the composition described above is also described.
- Additional embodiments described include the method described above where the applying step is performed post-emergently after the crop breaks ground; and the method described above where the applying step is performed pre- emergently before the crop breaks ground.
- Clethodim for example
- microcapsules are formed through conventional complex coacervation techniques.
- this encapsulation technology and one or more appropriate surfactants, the new delivery system demonstrates many advantages, including the following to name just a few:
- the oil phase acts as a built-in adjuvant for improving bio efficacy for oil dispersions.
- composition materials are first hydrated and thoroughly mixed (1).
- the solutions are prepared by dispersing the composition materials in a concentration from 2% to 50% by weight based on their molecular weights and the desired viscosity of the final solutions, i.e. balanced viscosity for product handling and minimized phase separation.
- the solutions are gently stirred and stored, for example, overnight to ensure complete hydration of the biopolymers (2). Heat may be applied to enhance dissolving if necessary.
- the biopolymer solution or a mixture of biopolymer solutions are mixed in a beaker with appropriate surfactants (3).
- a Clethodim solution in a concentration from 50% to 80% is then metered into the breaker (4) and
- micro-emulsion mixture is further spray-dried (6) with an air flow whose inlet temperature is from 110 °C to 120 °C.
- the microcapsule powder is collected and analyzed.
- the microcapsule powder can be further made into an Oil Dispersion by suspending the powder into one or more selected oils in a concentration from 20% to 90% under agitation.
- one or more surfactants including dispersants, emulsifiers, rheology aids are added into the Oil Dispersion to stabilize the mixture.
- the oil dispersion is analyzed below.
- the commercial EC product contains 120 g/L of Clethodim
- the water based dispersions can contain functional materials such as: Cyclohexanediones such as Clethodim, Polysaccharides such as Inulin, Natural gums such as Gum Arabic,
- Polysaccharides such as maltodextrin, starches and polysaccharides such as Waxy Maize Starch, proteins such as Whey Protein, Sugar Alcohols such as Sorbitol and Mannitol, Polysaccharide starches, Cyclic oligosaccharide such as Cyclodextrin; conventional surfactants such as Polyoxyethylene (20) sorbitan monolaurate, Alkylated vinyl- pyrrolidone polymer, Isopropyl alcohol, EO/PO (ethylene oxide/propylene oxide) block copolymer, Anionic polymeric dispersant
- Polyalkylene oxide block copolymer Polyalkylene oxide block copolymer, nonionic block copolymer , Butyl block copolymer, and Polyvinylpyrrolidone Water soluble polymer.
- the oil based dispersions can also contain functional materials such as: conventional surfactants such as EO/PO (ethylene oxide/propylene oxide) block copolymer, Polyalkylene oxide block copolymer, EO/PO block copolymer, nonionic block copolymer, Butyl block copolymer, Polyvinylpyrrolidone Water soluble polymer, anionic polymeric dispersant, cetyl ether phosphate, oleyl ether phosphate, polyoxyethylene (5) oleyl mono/di-phosphate, polyoxyethylene (3) oleyl mono/di-phosphate, sodium dioctyl- sulfosuccinate, polyoxyethylene (40) sorbitol hexaoleate, ethoxylated castor oil and rapeseed oil fatty acid methyl ester.
- conventional surfactants such as EO/PO (ethylene oxide/propylene oxide) block copolymer, Polyalkylene oxide block copolymer, EO
Landscapes
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicinal Preparation (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2021524423A JP2022506820A (ja) | 2018-11-13 | 2019-11-12 | シクロヘキサンジオン封入プロセス及び製品 |
| PE2021000703A PE20211200A1 (es) | 2018-11-13 | 2019-11-12 | Proceso de encapsulacion de ciclohexanodionas y producto |
| UAA202103140A UA129424C2 (uk) | 2018-11-13 | 2019-11-12 | Спосіб і продукт інкапсуляції циклогександіонів |
| CA3119291A CA3119291A1 (en) | 2018-11-13 | 2019-11-12 | Encapsulation of cyclohexanediones process and product |
| CN201980074191.7A CN112996389A (zh) | 2018-11-13 | 2019-11-12 | 环己二酮胶囊包封方法和产品 |
| EP19884308.8A EP3879981B1 (en) | 2018-11-13 | 2019-11-12 | Encapsulation of clethodim, process and product |
| PL19884308.8T PL3879981T3 (pl) | 2018-11-13 | 2019-11-12 | Proces i produkt enkapsulacji kletodymu |
| MX2021005571A MX2021005571A (es) | 2018-11-13 | 2019-11-12 | Proceso de encapsulacion de ciclohexanodionas y producto. |
| CR20210245A CR20210245A (es) | 2018-11-13 | 2019-11-12 | Proceso de encapsulación de ciclohexanodionas y producto |
| AU2019378776A AU2019378776B2 (en) | 2018-11-13 | 2019-11-12 | Encapsulation of cyclohexanediones process and product |
| MYPI2021002618A MY203998A (en) | 2018-11-13 | 2019-11-12 | Encapsulation of cyclohexanediones process and product |
| EA202191202A EA202191202A1 (ru) | 2018-11-13 | 2019-11-12 | Процесс и продукт инкапсуляции циклогександионов |
| US17/291,508 US12414563B2 (en) | 2018-11-13 | 2019-11-12 | Encapsulation of cyclohexanediones process and product |
| PH12021551051A PH12021551051A1 (en) | 2018-11-13 | 2021-05-06 | Encapsulation of cyclohexanediones process and product |
| CONC2021/0006095A CO2021006095A2 (es) | 2018-11-13 | 2021-05-11 | Proceso de encapsulación de ciclohexanodionas y producto |
| ZA2021/03218A ZA202103218B (en) | 2018-11-13 | 2021-05-12 | Encapsulation of cyclohexanediones process and product |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201862760565P | 2018-11-13 | 2018-11-13 | |
| US62/760,565 | 2018-11-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2020102232A1 true WO2020102232A1 (en) | 2020-05-22 |
Family
ID=70730819
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US2019/060981 Ceased WO2020102232A1 (en) | 2018-11-13 | 2019-11-12 | Encapsulation of cyclohexanediones process and product |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US12414563B2 (enExample) |
| EP (1) | EP3879981B1 (enExample) |
| JP (1) | JP2022506820A (enExample) |
| CN (1) | CN112996389A (enExample) |
| AR (1) | AR117050A1 (enExample) |
| AU (1) | AU2019378776B2 (enExample) |
| CA (1) | CA3119291A1 (enExample) |
| CL (1) | CL2021001231A1 (enExample) |
| CO (1) | CO2021006095A2 (enExample) |
| CR (1) | CR20210245A (enExample) |
| EA (1) | EA202191202A1 (enExample) |
| EC (1) | ECSP21034011A (enExample) |
| MX (1) | MX2021005571A (enExample) |
| MY (1) | MY203998A (enExample) |
| NI (1) | NI202100037A (enExample) |
| PE (1) | PE20211200A1 (enExample) |
| PH (1) | PH12021551051A1 (enExample) |
| PL (1) | PL3879981T3 (enExample) |
| UA (1) | UA129424C2 (enExample) |
| WO (1) | WO2020102232A1 (enExample) |
| ZA (1) | ZA202103218B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2020408324B2 (en) * | 2019-12-18 | 2026-06-18 | Sumitomo Chemical Company, Limited | Agricultural compositions and methods of use thereof |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2026098876A1 (en) * | 2024-11-05 | 2026-05-15 | Syngenta Crop Protection Ag | Agrochemical composition for precision application |
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| US4952722A (en) * | 1982-02-12 | 1990-08-28 | Ici Australia Limited | Compounds and compositions |
| US5922357A (en) * | 1994-03-28 | 1999-07-13 | University Of Nottingham | Polymer microspheres and a method of production thereof |
| CN101396018A (zh) * | 2008-09-05 | 2009-04-01 | 河北科技大学 | 除草剂稀禾定的脲醛树脂微胶囊剂及其制备方法 |
| CN101427672A (zh) | 2008-12-16 | 2009-05-13 | 冯薇 | 除草剂稀禾定的微胶囊水悬剂及其制备方法 |
| US20100248963A1 (en) * | 2009-02-13 | 2010-09-30 | Monsanto Technology Llc | Encapsulation of Herbicides to Reduce Crop Injury |
| CN101990890A (zh) | 2010-11-16 | 2011-03-30 | 北京颖新泰康国际贸易有限公司 | 环己烯酮型除草剂微胶囊及其制备方法 |
| US20110301036A1 (en) * | 2010-06-07 | 2011-12-08 | Dow Agrosciences Llc | Microcapsule suspensions including high levels of agriculturally active ingredients |
| CN102388864A (zh) * | 2011-09-20 | 2012-03-28 | 中国科学院化学研究所 | 一种农药微胶囊及其制备方法 |
| WO2012080208A1 (en) * | 2010-12-14 | 2012-06-21 | Lamberti Spa | Agrochemical oil dispersion |
| WO2013158620A1 (en) | 2012-04-16 | 2013-10-24 | North Carolina State University | Nanotechnology system for agricultural applications |
| US20140080712A1 (en) | 2012-09-17 | 2014-03-20 | Agrofresh Inc. | Compositions and methods for double encapsulation of a volatile compound |
| US20180139956A1 (en) * | 2015-05-20 | 2018-05-24 | Ishihara Sangyo Kaisha, Ltd. | Microcapsule suspension |
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-
2019
- 2019-11-12 CN CN201980074191.7A patent/CN112996389A/zh active Pending
- 2019-11-12 UA UAA202103140A patent/UA129424C2/uk unknown
- 2019-11-12 CA CA3119291A patent/CA3119291A1/en active Pending
- 2019-11-12 PE PE2021000703A patent/PE20211200A1/es unknown
- 2019-11-12 EA EA202191202A patent/EA202191202A1/ru unknown
- 2019-11-12 MX MX2021005571A patent/MX2021005571A/es unknown
- 2019-11-12 AU AU2019378776A patent/AU2019378776B2/en active Active
- 2019-11-12 US US17/291,508 patent/US12414563B2/en active Active
- 2019-11-12 AR ARP190103315A patent/AR117050A1/es active IP Right Grant
- 2019-11-12 CR CR20210245A patent/CR20210245A/es unknown
- 2019-11-12 PL PL19884308.8T patent/PL3879981T3/pl unknown
- 2019-11-12 WO PCT/US2019/060981 patent/WO2020102232A1/en not_active Ceased
- 2019-11-12 JP JP2021524423A patent/JP2022506820A/ja active Pending
- 2019-11-12 MY MYPI2021002618A patent/MY203998A/en unknown
- 2019-11-12 EP EP19884308.8A patent/EP3879981B1/en active Active
-
2021
- 2021-05-06 PH PH12021551051A patent/PH12021551051A1/en unknown
- 2021-05-11 CL CL2021001231A patent/CL2021001231A1/es unknown
- 2021-05-11 CO CONC2021/0006095A patent/CO2021006095A2/es unknown
- 2021-05-12 ZA ZA2021/03218A patent/ZA202103218B/en unknown
- 2021-05-12 NI NI202100037A patent/NI202100037A/es unknown
- 2021-05-12 EC ECSENADI202134011A patent/ECSP21034011A/es unknown
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| US4952722A (en) * | 1982-02-12 | 1990-08-28 | Ici Australia Limited | Compounds and compositions |
| US5922357A (en) * | 1994-03-28 | 1999-07-13 | University Of Nottingham | Polymer microspheres and a method of production thereof |
| CN101396018A (zh) * | 2008-09-05 | 2009-04-01 | 河北科技大学 | 除草剂稀禾定的脲醛树脂微胶囊剂及其制备方法 |
| CN101427672A (zh) | 2008-12-16 | 2009-05-13 | 冯薇 | 除草剂稀禾定的微胶囊水悬剂及其制备方法 |
| US20100248963A1 (en) * | 2009-02-13 | 2010-09-30 | Monsanto Technology Llc | Encapsulation of Herbicides to Reduce Crop Injury |
| US20110301036A1 (en) * | 2010-06-07 | 2011-12-08 | Dow Agrosciences Llc | Microcapsule suspensions including high levels of agriculturally active ingredients |
| CN101990890A (zh) | 2010-11-16 | 2011-03-30 | 北京颖新泰康国际贸易有限公司 | 环己烯酮型除草剂微胶囊及其制备方法 |
| WO2012080208A1 (en) * | 2010-12-14 | 2012-06-21 | Lamberti Spa | Agrochemical oil dispersion |
| CN102388864A (zh) * | 2011-09-20 | 2012-03-28 | 中国科学院化学研究所 | 一种农药微胶囊及其制备方法 |
| WO2013158620A1 (en) | 2012-04-16 | 2013-10-24 | North Carolina State University | Nanotechnology system for agricultural applications |
| US20140080712A1 (en) | 2012-09-17 | 2014-03-20 | Agrofresh Inc. | Compositions and methods for double encapsulation of a volatile compound |
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| Title |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2020408324B2 (en) * | 2019-12-18 | 2026-06-18 | Sumitomo Chemical Company, Limited | Agricultural compositions and methods of use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| EP3879981A4 (en) | 2021-12-15 |
| ECSP21034011A (es) | 2021-06-30 |
| ZA202103218B (en) | 2024-10-30 |
| EP3879981B1 (en) | 2024-07-24 |
| CA3119291A1 (en) | 2020-05-22 |
| EA202191202A1 (ru) | 2021-07-27 |
| CN112996389A (zh) | 2021-06-18 |
| CO2021006095A2 (es) | 2021-10-29 |
| NI202100037A (es) | 2021-10-01 |
| EP3879981A1 (en) | 2021-09-22 |
| US20220000105A1 (en) | 2022-01-06 |
| CR20210245A (es) | 2021-07-07 |
| MY203998A (en) | 2024-07-30 |
| UA129424C2 (uk) | 2025-04-23 |
| US12414563B2 (en) | 2025-09-16 |
| PL3879981T3 (pl) | 2024-12-16 |
| AU2019378776B2 (en) | 2025-02-20 |
| CL2021001231A1 (es) | 2021-11-19 |
| PE20211200A1 (es) | 2021-07-01 |
| AU2019378776A1 (en) | 2021-06-03 |
| MX2021005571A (es) | 2021-07-06 |
| JP2022506820A (ja) | 2022-01-17 |
| PH12021551051A1 (en) | 2021-12-13 |
| AR117050A1 (es) | 2021-07-07 |
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