WO2020102232A1 - Encapsulation of cyclohexanediones process and product - Google Patents

Encapsulation of cyclohexanediones process and product Download PDF

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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
Application number
PCT/US2019/060981
Other languages
English (en)
French (fr)
Inventor
Hong Zhang
Rachel Louise BRANAGHAN
Sarah Jane MAUDE
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Arysta LifeScience Inc
Original Assignee
Arysta LifeScience Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to AU2019378776A priority Critical patent/AU2019378776B2/en
Priority to JP2021524423A priority patent/JP2022506820A/ja
Priority to PE2021000703A priority patent/PE20211200A1/es
Priority to UAA202103140A priority patent/UA129424C2/uk
Priority to CA3119291A priority patent/CA3119291A1/en
Priority to CN201980074191.7A priority patent/CN112996389A/zh
Priority to EP19884308.8A priority patent/EP3879981B1/en
Priority to PL19884308.8T priority patent/PL3879981T3/pl
Priority to CR20210245A priority patent/CR20210245A/es
Priority to MX2021005571A priority patent/MX2021005571A/es
Priority to EA202191202A priority patent/EA202191202A1/ru
Priority to MYPI2021002618A priority patent/MY203998A/en
Application filed by Arysta LifeScience Inc filed Critical Arysta LifeScience Inc
Priority to US17/291,508 priority patent/US12414563B2/en
Publication of WO2020102232A1 publication Critical patent/WO2020102232A1/en
Priority to PH12021551051A priority patent/PH12021551051A1/en
Priority to CONC2021/0006095A priority patent/CO2021006095A2/es
Priority to ZA2021/03218A priority patent/ZA202103218B/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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)
PCT/US2019/060981 2018-11-13 2019-11-12 Encapsulation of cyclohexanediones process and product Ceased WO2020102232A1 (en)

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)

* Cited by examiner, † Cited by third party
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

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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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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
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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
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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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Publication number Priority date Publication date Assignee Title
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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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