WO2020128511A1 - Encapsulated pesticide - Google Patents

Encapsulated pesticide Download PDF

Info

Publication number
WO2020128511A1
WO2020128511A1 PCT/GB2019/053659 GB2019053659W WO2020128511A1 WO 2020128511 A1 WO2020128511 A1 WO 2020128511A1 GB 2019053659 W GB2019053659 W GB 2019053659W WO 2020128511 A1 WO2020128511 A1 WO 2020128511A1
Authority
WO
WIPO (PCT)
Prior art keywords
product
pesticide
biopolymer
surfactant
solution
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/GB2019/053659
Other languages
French (fr)
Inventor
Graham HAIGH
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.)
Pangaea Agrochemicals Ltd
Original Assignee
Pangaea Agrochemicals Ltd
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 CN201980090968.9A priority Critical patent/CN113473862B/en
Priority to CR20210391A priority patent/CR20210391A/en
Priority to AU2019409025A priority patent/AU2019409025B2/en
Priority to US17/414,289 priority patent/US20220071202A1/en
Priority to KR1020217022468A priority patent/KR102918251B1/en
Priority to PH1/2021/551727A priority patent/PH12021551727A1/en
Priority to MX2021007407A priority patent/MX2021007407A/en
Priority to CA3124041A priority patent/CA3124041A1/en
Priority to MYPI2021003447A priority patent/MY207908A/en
Application filed by Pangaea Agrochemicals Ltd filed Critical Pangaea Agrochemicals Ltd
Priority to IL284105A priority patent/IL284105B2/en
Priority to JP2021536391A priority patent/JP7475066B2/en
Priority to BR112021012147-1A priority patent/BR112021012147B1/en
Priority to EP19839120.3A priority patent/EP3897155A1/en
Publication of WO2020128511A1 publication Critical patent/WO2020128511A1/en
Anticipated expiration legal-status Critical
Priority to CONC2021/0009336A priority patent/CO2021009336A2/en
Priority to ZA2021/05017A priority patent/ZA202105017B/en
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
    • 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
    • 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
    • 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
    • A01N25/30—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 characterised by the surfactants
    • 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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
    • B01J13/02—Making microcapsules or microballoons
    • B01J13/04—Making microcapsules or microballoons by physical processes, e.g. drying, spraying

Definitions

  • the present invention relates to a method for encapsulating a pesticide, and in particular to a method which avoids the need for forming an emulsion. It also relates to an encapsulated pesticide formed according to the method, and to methods of using the pesticide with or without an adjuvant. More particularly it relates to a pesticide which is a herbicide.
  • Herbicides are commonly used in agriculture to improve the productivity and quality of the grown product.
  • the global market for herbicides is estimated to reach $31.5 billion by 2020.
  • Asia-Pacific is the dominant market accounting for two fifth of herbicide use, whereas North America region equates to one-third of global revenue generated by the herbicide market.
  • EP 1 499 183 B2 discloses a method for preventing or reducing resistance to a pesticide of a substrate pest, which method comprises administering to the substrate or the pest a metabolic enzyme inhibitor (such as piperonyl butoxide - PBO) and (substantially simultaneously) a pesticide (such as a pyrethroid insecticide) encapsulated in a degradable capsule.
  • a metabolic enzyme inhibitor such as piperonyl butoxide - PBO
  • a pesticide such as a pyrethroid insecticide
  • the capsule prevents an effective dose of the pesticide from being absorbed by the pest until the inhibitor has had time to begin its inhibiting effect on the substrate.
  • the formulation used in this case is Karate Zeon® which is a PVA-encapsulated insecticide (lambda-cyhalothrin) produced by Syngenta.
  • EP 0427991 A1 (Sumitomo Chemical Co.) discloses an insecticidal and/or acaricidal and/or nematicidal composition which is a mixture of an encapsulated part which is formed of water-insoluble microcapsules and a flowable part which is emulsified or suspended in water.
  • US 2015/320036 A1 discloses a process for obtaining biopolymeric nanoparticles containing Azadirachta indica A.
  • Juss (Neem), which comprises, in Phase I, preparing an aqueous emulsion of Neem oil and extracts, in Phase II, preparing a biopolymer solution in organic solvent, followed by mixture of both Phases I and II, and, in Phase III, preparing an aqueous emulsion of a surfactant and adding it to the Phase I and II mixture, affording a nanoparticle suspension which is stabilized.
  • Biopolymeric nanoparticles and powder microparticles obtained are also described.
  • US 2016/0330952 A1 discloses methods for the encapsulation of volatile organic compounds by formation of stable emulsions of the volatile organic compound that are mixed with encapsulating polymer solutions and then formed into ultrafme fibers.
  • the ultrafme fibers containing the encapsulated volatile organic compounds can be formed into a variety of formats for use to preserve perishable products.
  • a method for encapsulating a pesticide including the steps of combining a pesticide in solution with a first biopolymer and a second biopolymer and a surfactant.
  • the method includes the steps of: (a) mixing the first biopolymer and the second biopolymer in solution,
  • step (b) adding the product of step (a) to a solution of pesticide
  • step (c) adding the surfactant to the product of step (b).
  • the first biopolymer is an alginate
  • the second biopolymer is a pectin
  • the surfactant is a cocoamine surfactant
  • the inventive method is able to produce an encapsulated pesticide without needing to produce an emulsion (either oil-in-water or water-in-oil). This has substantial advantages both environmentally (avoiding the need to use organic solvents) and commercially (because expensive washing steps are not needed).
  • the process can be performed in a single vessel, avoiding the need for centrifugation or filtering steps.
  • the product also has suitable pesticide release properties.
  • the first biopolymer is preferably an alginate with a viscosity from 4 to 100 centipoise (for e.g. a 1 w/v % solution).
  • a viscosity from 4 to 100 centipoise for e.g. a 1 w/v % solution.
  • the use of a low viscosity alginate ensures that the resulting product has suitable rheological properties for application to plants (for example).
  • calcium ions may be added as it is believed (without wishing to be constrained by theory) that these can result in a more stable encapsulated product.
  • the use of hard water is believed to provide a sufficient level of calcium ions.
  • Figure l is a schematic diagram illustrating the preparation of microcapsules via the Emulsion-gelation method.
  • Figure 2 is a graph showing the cumulative glyphosate release over time from capsules encapsulated in accordance with the invention.
  • Glacial acetic acid Glacial acetic acid (Fisher Scientific; A/0360/PB17).
  • chitosan where 1 % solution was prepared in 1 % (v/v) acetic acid, which was also prepared in distilled water.
  • the mixed coating solutions were prepared by stirring the required w/w ratios of the individual coating solutions for 5 min prior to the addition of glyphosate salt to ensure homogeneous mixture.
  • the resultant solution was added dropwise to a stirred 250 ml breaker containing sunflower oil (100 ml) to form an emulsion using a homogeniser (IKA) at 1000 rpm with blade diameter 27 mm.
  • IKA homogeniser
  • Step two Premix B In a clean stainless-steel mixing vessel with suitable extraction, mixing and temperature, add 267 Kilograms Glyphosate-Isopropylammonium salt 620 g/kg (to give 122 g/1 approx.)
  • Premix A 40 Kilograms
  • the ee for the capsules were determined via thoroughly grinding the capsules (100 mg) periodically for 1 min after intervals of 15 min over 1 h using a mortar and pestle in an aqueous solution of potassium dihydrogen phosphite buffer (5ml). ⁇ After 1 h, the ground mixtures were filtered (0.45 pm) and samples were run by
  • Capsules to be tested were placed in a dialysis tube (lg in 50ml water) and mixed at 150rpm at 25°C and 35% humidity. Capsules were then sampled at different times to analyse glyphosate release using HPLC.

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Environmental Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • Wood Science & Technology (AREA)
  • Pest Control & Pesticides (AREA)
  • Chemical & Material Sciences (AREA)
  • Toxicology (AREA)
  • Organic Chemistry (AREA)
  • Dispersion Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

A method for encapsulating a pesticide(for example glyphosate) includes the steps of (a) mixing a first biopolymer which is an alginate with a viscosity from 4 to 100 centipoise (a 1% aqueous solution at 20 centigrade) and a second biopolymer in solution, (b) adding the product of step (a) to a solution of pesticide, and (c) adding a surfactant to the product of step (b).

Description

Encapsulated pesticide
The present invention relates to a method for encapsulating a pesticide, and in particular to a method which avoids the need for forming an emulsion. It also relates to an encapsulated pesticide formed according to the method, and to methods of using the pesticide with or without an adjuvant. More particularly it relates to a pesticide which is a herbicide.
Herbicides are commonly used in agriculture to improve the productivity and quality of the grown product. The global market for herbicides is estimated to reach $31.5 billion by 2020. Asia-Pacific is the dominant market accounting for two fifth of herbicide use, whereas North America region equates to one-third of global revenue generated by the herbicide market.
At present, the most widely used herbicide in the world is glyphosate, which has global sales amounting to more than $10 billion per year due to low cost production and low
environmental impact.
As a result of the prolonged use of herbicides, weeds are becoming resistant and this is increasing exponentially with over 217 weed species presently resistant around the world. In most cases, it is estimated that weed resistance will emerge within three years on a piece of land which has been treated with a given herbicide.
Current solutions are either to develop novel herbicides or switch from glyphosate-ready to glufosinate-ready crops. Both alternatives are expensive and there are no guarantees that the weed will not become resistant after 3-5 years. In case of the herbicide glufosinate, weed- resistance has already been reported. The first cases of weed-resistance were reported in 2009 and increasing use of the herbicide is likely to result in widespread resistance.
Other alternatives are to use higher dosages of glyphosate, which could be detrimental to the environment or in extreme circumstances manual removal of the weeds, which is labour intensive. Both alternatives lead to higher costs or danger of ruining the fertile land.
EP 1 499 183 B2 (Rothamsted Research Institute Limited et al.) discloses a method for preventing or reducing resistance to a pesticide of a substrate pest, which method comprises administering to the substrate or the pest a metabolic enzyme inhibitor (such as piperonyl butoxide - PBO) and (substantially simultaneously) a pesticide (such as a pyrethroid insecticide) encapsulated in a degradable capsule. The capsule prevents an effective dose of the pesticide from being absorbed by the pest until the inhibitor has had time to begin its inhibiting effect on the substrate. The formulation used in this case is Karate Zeon® which is a PVA-encapsulated insecticide (lambda-cyhalothrin) produced by Syngenta.
EP 0427991 A1 (Sumitomo Chemical Co.) discloses an insecticidal and/or acaricidal and/or nematicidal composition which is a mixture of an encapsulated part which is formed of water-insoluble microcapsules and a flowable part which is emulsified or suspended in water.
US 2015/320036 A1 discloses a process for obtaining biopolymeric nanoparticles containing Azadirachta indica A. Juss (Neem), which comprises, in Phase I, preparing an aqueous emulsion of Neem oil and extracts, in Phase II, preparing a biopolymer solution in organic solvent, followed by mixture of both Phases I and II, and, in Phase III, preparing an aqueous emulsion of a surfactant and adding it to the Phase I and II mixture, affording a nanoparticle suspension which is stabilized. Biopolymeric nanoparticles and powder microparticles obtained are also described.
US 2016/0330952 A1 discloses methods for the encapsulation of volatile organic compounds by formation of stable emulsions of the volatile organic compound that are mixed with encapsulating polymer solutions and then formed into ultrafme fibers. The ultrafme fibers containing the encapsulated volatile organic compounds can be formed into a variety of formats for use to preserve perishable products.
The present applicant has filed International Patent Application No. PCT/GB2018/051864 (unpublished at the date of filing the present application) which seeks to provide an improved encapsulated pesticide. The present application seeks to provide yet a further improvement, and in particular an improved method which is commercially suitable for industrial production of the encapsulated pesticide.
In accordance with a first aspect of the present invention, there is provided a method for encapsulating a pesticide, including the steps of combining a pesticide in solution with a first biopolymer and a second biopolymer and a surfactant. Preferably, the method includes the steps of: (a) mixing the first biopolymer and the second biopolymer in solution,
(b) adding the product of step (a) to a solution of pesticide, and
(c) adding the surfactant to the product of step (b).
In a particularly preferred embodiment, the first biopolymer is an alginate, the second biopolymer is a pectin and the surfactant is a cocoamine surfactant.
It has been discovered that the inventive method is able to produce an encapsulated pesticide without needing to produce an emulsion (either oil-in-water or water-in-oil). This has substantial advantages both environmentally (avoiding the need to use organic solvents) and commercially (because expensive washing steps are not needed). In addition, the process can be performed in a single vessel, avoiding the need for centrifugation or filtering steps. The product also has suitable pesticide release properties.
The first biopolymer is preferably an alginate with a viscosity from 4 to 100 centipoise (for e.g. a 1 w/v % solution). The use of a low viscosity alginate ensures that the resulting product has suitable rheological properties for application to plants (for example).
In a preferred embodiment, calcium ions may be added as it is believed (without wishing to be constrained by theory) that these can result in a more stable encapsulated product. The use of hard water is believed to provide a sufficient level of calcium ions.
A number of preferred embodiments of the invention will now be described with reference to and as illustrated in the accompanying drawings, in which:
Figure l is a schematic diagram illustrating the preparation of microcapsules via the Emulsion-gelation method; and
Figure 2 is a graph showing the cumulative glyphosate release over time from capsules encapsulated in accordance with the invention.
Experimental
Materials All the chemicals were purchased from either Aldrich or Fisher Scientific, whereas the solvents were purchased from Fisher Scientific.
• Alginic acid sodium salt from brown algae (Aldrich; product number A0682).
• Pectin from citrius peel with galactaronic acid > 74 % (Aldrich; product number P9135).
• Chitosan from crab shell, with at least 85% deacylated (Aldrich; product number 48165).
• Gelatine from bovine skin with around 75 bloom (Aldrich).
• Calcium chloride anhydrous powder (Fisher Scientific; product number
1.02378.2500).
• Glacial acetic acid (Fisher Scientific; A/0360/PB17).
• Phosphoric acid (Aldrich; product number 79617).
• Glyphosate (99 %, Aldrich: product number 455251).
• The 67 % glyphosate isopropylammonium solution was supplied by Pangea
Chemicals.
• Isopropylamine (Aldrich: product number 471291).
• Sunflower oil (supermarket brand; ASDA).
COMPARATIVE EXAMPLE A
Emulsion-gelation method
• Aqueous solutions of 4 % (w/w) of coating materials were prepared in distilled water.
The only exception being chitosan where 1 % solution was prepared in 1 % (v/v) acetic acid, which was also prepared in distilled water. • For the formulations containing the mixed coatings; the mixed coating solutions were prepared by stirring the required w/w ratios of the individual coating solutions for 5 min prior to the addition of glyphosate salt to ensure homogeneous mixture.
• An aqueous solution of coating material (25 g) was mixed with aqueous solution of 67 % (w/w) glyphosate isopropylammonium solution (5 g) using a magnetic stirrer at 200 rpm for 2 min.
• The resultant solution was added dropwise to a stirred 250 ml breaker containing sunflower oil (100 ml) to form an emulsion using a homogeniser (IKA) at 1000 rpm with blade diameter 27 mm.
• After 30 min, calcium chloride (1 g) powder was added slowly over 10 min. Small portions of powder (0.1 g) was sprinkled using a stainless steel spatula to ensure the powder was evenly distributed over the reaction vessel. The calcium chloride reacts instantaneously when it comes in contact with the coating material.
• The resultant reaction mixture was further stirred for 30 min at 1000 rpm using a homogenizer. Observe formation of white capsules settling to the bottom of the breaker.
• The resultant reaction mixture was separated in two centrifuge tubes (50 ml) and centrifuged for 10 min at 3300 rpm.
• The supernatant was discarded.
• Hexane (50 ml) was added to each centrifuge tube (50 ml volume) and the suspension centrifuged for 10 min at 3300 rpm.
• The supernatant was decanted and the process was repeated once again.
• The microcapsules were placed under high vacuum overnight to remove remaining solvent residue. EXAMPLE B
Experimental preparation of Glyphosate 120 g/1 CS - lOOOLts
Step one: Premix A
In a stainless-steel ribbon blender, mix the following components: 30 Kilograms low viscosity sodium alginate (1% solution with a viscosity of less than 20 cps)
10 Kilograms pectin, specification of greater 74% Galacturonic acid which suggests the esterification is less than 26%
Mix the above for 30 minutes at a rate between 5 and 10 RPM
Step two: Premix B In a clean stainless-steel mixing vessel with suitable extraction, mixing and temperature, add 267 Kilograms Glyphosate-Isopropylammonium salt 620 g/kg (to give 122 g/1 approx.)
Warm and maintain the above 45 to 55°C
Start the propeller mixer at a speed to produce a vortex in the liquid.
Slowly add Premix A (40 Kilograms) into the vortex at a speed so no obvious lumps form. Once added, slow the mixer to a speed such that no additional air is added into the solution, remove the heat source and allow the product to stir whilst the temperature returns to ambient.
**** Sample liquid, all Premix A must have dissolved into the Glyphosate IPA Salt, this can take between 2 and 24 hours subject to Alginate / Pectin source. Step three: final product
Take 307 Kilograms of the product of Step 2
Maintain slow agitation, do not incorporate any air bubbles. Slowly add at a rate of 100 Kilograms / Hour 622.5 Kilograms WHO standard hard water (The calcium required comes from the water hardness)
Then add
160.0 Kilograms Surfactant LKD 1559 2.5 Kilograms Acid Blue 9 concentrate
0.1 Kilograms Citrus Burst WS
Total = 1092.1 Kilograms / 1000 Litres
RESULTS Capsule Characterisation
Encapsulation Efficiency (ee)
• The ee for the capsules were determined via thoroughly grinding the capsules (100 mg) periodically for 1 min after intervals of 15 min over 1 h using a mortar and pestle in an aqueous solution of potassium dihydrogen phosphite buffer (5ml). · After 1 h, the ground mixtures were filtered (0.45 pm) and samples were run by
HPLC to determine the glyphosate concentration. Each experiment was repeated three times for each capsule.
The results for the capsules of Comparative Example A and Example B are shown in Table 1 below:
Figure imgf000008_0001
Figure imgf000009_0001
Glyphosate Release Studies
These were carried out using HPLC. Capsules to be tested were placed in a dialysis tube (lg in 50ml water) and mixed at 150rpm at 25°C and 35% humidity. Capsules were then sampled at different times to analyse glyphosate release using HPLC.
The release profile for the capsules of Comparative Example A (labelled“Birmingham”) and Example B (labelled“AgroSmart capsules”) are shown in Figure 1 below. It can be seen that comparable release profiles are obtained despite the difference in encapsulation methods.
All optional and preferred features and modifications of the described embodiments and dependent claims are usable in all aspects of the invention taught herein. Furthermore, the individual features of the dependent claims, as well as all optional and preferred features and modifications of the described embodiments are combinable and interchangeable with one another.
The disclosures in UK patent application number 1821031.0 from which this application claims priority, and in the abstract accompanying this application are incorporated herein by reference.

Claims

1. A method for encapsulating a pesticide, including the steps of
(a) mixing a first biopolymer which is an alginate with a viscosity from 4 to 100 centipoise (a 1% aqueous solution at 20 centigrade) and a second biopolymer in solution, (b) adding the product of step (a) to a solution of pesticide, and
(c) adding a surfactant to the product of step (b).
2. A method as claimed in claim 1, wherein the second biopolymer is a pectin or chitosan.
3. A method as claimed in claim 2, wherein the pectin is a citrus pectin.
4. A method as claimed in claim 2 or 3, wherein the pectin is in the form of an ester.
5. A method as claimed in claim 4, wherein the degree of esterification up to 30%.
6. A method as claimed in any preceding claim, wherein the surfactant is a cocoamine surfactant.
7. A method as claimed in any preceding claim, wherein the amount of surfactant is from 3% to 30%
8. A method as claimed in claim 7, wherein the amount of surfactant is about 16%.
9. A method as claimed in any preceding claim, wherein the ratio of the first to the second biopolymer is from 9: 1 to 1 :9.
10. A method as claimed in claim 9, wherein the ratio of the first to the second biopolymer is about 3: 1.
11. A method as claimed in any preceding claim, wherein in step (b) the product is stirred at a rate of stirring from 500 to 3000 RPM.
12. A method as claimed in claim 11, wherein the product is continuously stirred from 30 minutes to 24 hours.
13. A method as claimed in claim 11 or 12, wherein the product is stirred or agitated under a blanket of inert gas, optionally nitrogen.
14. A method as claimed in any of claims 11 to 13, wherein the product is stirred with a propeller, an anchor, a dissolver, a paddle, a swivel, a beater and turbine, a four-bladed impeller or a gate mixer.
15. A method as claimed in any preceding claim, wherein the pesticide is glyphosate, glufosinate, or any water-soluble pesticide.
16. A method as claimed in claim 15, wherein the pesticide is glyphosate in the form of a salt of ammonium, diammonium, dimethylammonium, isopropylammonium, potassium or sesquisodium.
17. A method as claimed in any preceding claim, wherein step (b) is carried out at a temperature from 40°C to 60°C.
18. A method as claimed in any preceding claim which is carried out in aqueous solution.
19. A method as claimed in any preceding claim, wherein the pesticide is provided in the form of a 62% solution in water.
20. A method as claimed in any preceding claim which is carried out as a continuous process or as a batch process.
21. A method as claimed in any preceding claim in which the amount of pesticide in the final product is from 0.2 w/v % to 40 w/v %.
22. An encapsulated pesticide obtainable or obtained by a method as claimed in any preceding claim.
23. An encapsulated pesticide as claimed in claim 22 with an activity of 0.36 w/v %, 0.72 w/v %, 12 w/v % or 18 w/v %.
24. A method of applying the product of claim 22 or 23 to a plant including the step of applying the product together with an adjuvant.
25. A method as claimed in claim 24, wherein the adjuvant is PBO.
26. A method of applying the product of claim 22 or 23 to a plant including the step of applying the product in the absence of an adjuvant.
PCT/GB2019/053659 2018-12-21 2019-12-20 Encapsulated pesticide Ceased WO2020128511A1 (en)

Priority Applications (15)

Application Number Priority Date Filing Date Title
MYPI2021003447A MY207908A (en) 2018-12-21 2019-12-20 Encapsulated pesticide
AU2019409025A AU2019409025B2 (en) 2018-12-21 2019-12-20 Encapsulated pesticide
IL284105A IL284105B2 (en) 2018-12-21 2019-12-20 Pesticides in capsules
KR1020217022468A KR102918251B1 (en) 2018-12-21 2019-12-20 encapsulated pesticides
PH1/2021/551727A PH12021551727A1 (en) 2018-12-21 2019-12-20 Encapsulated pesticide
MX2021007407A MX2021007407A (en) 2018-12-21 2019-12-20 Encapsulated pesticide.
CA3124041A CA3124041A1 (en) 2018-12-21 2019-12-20 Encapsulated pesticide
CN201980090968.9A CN113473862B (en) 2018-12-21 2019-12-20 Encapsulated Pesticides
US17/414,289 US20220071202A1 (en) 2018-12-21 2019-12-20 Encapsulated pesticide
CR20210391A CR20210391A (en) 2018-12-21 2019-12-20 Encapsulated pesticide
JP2021536391A JP7475066B2 (en) 2018-12-21 2019-12-20 Encapsulated Pesticides
BR112021012147-1A BR112021012147B1 (en) 2018-12-21 2019-12-20 METHOD FOR ENCAPSULATING A PESTICIDE AND METHODS FOR APPLYING AN ENCAPSULATED PESTICIDE TO A PLANT
EP19839120.3A EP3897155A1 (en) 2018-12-21 2019-12-20 Encapsulated pesticide
CONC2021/0009336A CO2021009336A2 (en) 2018-12-21 2021-07-16 Encapsulated pesticide
ZA2021/05017A ZA202105017B (en) 2018-12-21 2021-07-16 Encapsulated pesticide

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB1821031.0A GB2586771A (en) 2018-12-21 2018-12-21 Encapsulated pesticide
GB1821031.0 2018-12-21

Publications (1)

Publication Number Publication Date
WO2020128511A1 true WO2020128511A1 (en) 2020-06-25

Family

ID=65364450

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB2019/053659 Ceased WO2020128511A1 (en) 2018-12-21 2019-12-20 Encapsulated pesticide

Country Status (18)

Country Link
US (1) US20220071202A1 (en)
EP (1) EP3897155A1 (en)
JP (1) JP7475066B2 (en)
KR (1) KR102918251B1 (en)
CN (1) CN113473862B (en)
AU (1) AU2019409025B2 (en)
CA (1) CA3124041A1 (en)
CO (1) CO2021009336A2 (en)
CR (1) CR20210391A (en)
EC (1) ECSP21053984A (en)
GB (1) GB2586771A (en)
IL (1) IL284105B2 (en)
MA (1) MA54535A (en)
MX (1) MX2021007407A (en)
MY (1) MY207908A (en)
PH (1) PH12021551727A1 (en)
WO (1) WO2020128511A1 (en)
ZA (1) ZA202105017B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022118019A1 (en) 2020-12-01 2022-06-09 Pangaea Agrochemicals Limited Reduced surfactant pesticide formulations
IT202100002042A1 (en) 2021-02-01 2022-08-01 Ndg Natural Dev Group S R L HERBICIDAL COMPOSITION

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0427991A1 (en) 1989-11-10 1991-05-22 Sumitomo Chemical Company, Limited Improved pesticidal composition
US20070141165A1 (en) * 2004-08-11 2007-06-21 Yukiko Takakura Method for Manufacturing Microcapsules Containing Capsinoid
EP1499183B2 (en) 2002-04-29 2012-08-01 Rothamsted Research Limited Compositions and methods for preventing or reducing resistance ofinsects to insecticides
US20150320036A1 (en) 2013-01-25 2015-11-12 Fundação Universidade Federal De São Carlos Process for obtaining biopolymeric nanoparticles containing azadirachta indica a. juss. (neem.) oil and extracts, biopolymeric nanoparticles, and powder microparticles
US20160330952A1 (en) 2014-01-15 2016-11-17 University Of Guelph Encapsulation and controlled release of volatile organic compounds
WO2019008341A1 (en) * 2017-07-04 2019-01-10 Pangaea Agrochemicals Limited Encapsulated pesticide

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5750468A (en) * 1995-04-10 1998-05-12 Monsanto Company Glyphosate formulations containing etheramine surfactants
ITMI20010347A1 (en) * 2001-02-21 2002-08-21 Grisotech S A IMMUNOGLOBULIN AND POLYSACCHARID COMPLEXES FOR ORAL ABSORPTION ETRANS-MUCOSAL
NO20021592D0 (en) * 2002-04-04 2002-04-04 Fmc Biopolymer As Polysaccharide Capsules and Method of Preparation thereof
JP2007223907A (en) * 2006-02-21 2007-09-06 Sumika Enviro-Science Co Ltd Microcapsule formulation and method for producing the same
EP2487192B1 (en) * 2006-03-30 2021-03-03 FMC Corporation Microencapsulation of clomazone by means of a refined process and specific microcapsules produced thereof
EP1844653B1 (en) * 2006-03-30 2017-07-26 GAT Microencapsulation GmbH Novel agrochemical formulations containing microcapsules
US8822381B2 (en) * 2008-12-31 2014-09-02 Marrone Bio Innovations, Inc. Uses of thaxtomin and thaxtomin compositions as herbicides
WO2010117740A2 (en) * 2009-03-28 2010-10-14 Tyratech, Inc. Enhanced formulations, compositions and methods for pest control
UA107670C2 (en) * 2009-08-07 2015-02-10 Dow Agrosciences Llc Meso-sized capsules useful for the delivery of agricultural chemicals
ES2386177B1 (en) * 2010-09-21 2013-09-23 Lipotec, S.A. NANOCAPSULES CONTAINING MICROEMULSIONS
TWI556737B (en) * 2011-02-11 2016-11-11 陶氏農業科學公司 Improved insecticide formulations
CN103340197B (en) * 2013-07-24 2015-05-27 中国农业大学 Slow/controlled-release microcapsule pesticide and preparation method thereof
US10307723B2 (en) * 2014-11-07 2019-06-04 Basf Se Process for preparing microcapsules having a polyurea shell and a lipophilic core material
KR20170078805A (en) * 2014-11-07 2017-07-07 바스프 에스이 Microcapsules comprising hydroxyalkyl cellulose
WO2016108234A1 (en) * 2014-12-30 2016-07-07 Yissum Research Develoment Company Of The Hebrew University Of Jerusalem Ltd. Liquid-core capsules comprising non-crosslinked alginate

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0427991A1 (en) 1989-11-10 1991-05-22 Sumitomo Chemical Company, Limited Improved pesticidal composition
EP1499183B2 (en) 2002-04-29 2012-08-01 Rothamsted Research Limited Compositions and methods for preventing or reducing resistance ofinsects to insecticides
US20070141165A1 (en) * 2004-08-11 2007-06-21 Yukiko Takakura Method for Manufacturing Microcapsules Containing Capsinoid
US20150320036A1 (en) 2013-01-25 2015-11-12 Fundação Universidade Federal De São Carlos Process for obtaining biopolymeric nanoparticles containing azadirachta indica a. juss. (neem.) oil and extracts, biopolymeric nanoparticles, and powder microparticles
US20160330952A1 (en) 2014-01-15 2016-11-17 University Of Guelph Encapsulation and controlled release of volatile organic compounds
WO2019008341A1 (en) * 2017-07-04 2019-01-10 Pangaea Agrochemicals Limited Encapsulated pesticide

Non-Patent Citations (8)

* Cited by examiner, † Cited by third party
Title
CINTIA RODRIGUES MARUYAMA ET AL: "Nanoparticles Based on Chitosan as Carriers for the Combined Herbicides Imazapic and Imazapyr", SCIENTIFIC REPORTS, vol. 6, no. 1, 27 January 2016 (2016-01-27), XP055672457, DOI: 10.1038/srep19768 *
GERMÃ N A ISLAN ET AL: "Studies of Ciprofloxacin Encapsulation on Alginate/Pectin Matrixes and Its Relationship with Biodisponibility", APPLIED BIOCHEMISTRY AND BIOTECHNOLOGY ; PART A: ENZYME ENGINEERING AND BIOTECHNOLOGY, HUMANA PRESS INC, NEW YORK, vol. 167, no. 5, 28 February 2012 (2012-02-28), pages 1408 - 1420, XP035087998, ISSN: 1559-0291, DOI: 10.1007/S12010-012-9610-2 *
GERSTL Z ET AL: "Controlled release of pesticides into water from clay -polymer formulations", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, AMERICAN CHEMICAL SOCIETY, BOOKS AND JOURNALS DIVISION, US, vol. 46, 1 September 1998 (1998-09-01), pages 3803 - 3809, XP002205376, ISSN: 0021-8561, DOI: 10.1021/JF980184P *
LOCATELLI GABRIEL OLIVO ET AL: "Development ofTrichodermasp. formulations in encapsulated granules (CG) and evaluation of conidia shelf-life", BIOLOGICAL CONTROL, vol. 117, 1 September 2017 (2017-09-01), pages 21 - 29, XP085318454, ISSN: 1049-9644, DOI: 10.1016/J.BIOCONTROL.2017.08.020 *
M. D. LOPEZ ET AL: "Development of Formulations to Improve the Controlled-Release of Linalool to Be Applied As an Insecticide", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, vol. 60, no. 5, 27 January 2012 (2012-01-27), US, pages 1187 - 1192, XP055672458, ISSN: 0021-8561, DOI: 10.1021/jf204242x *
MARIANA DOS SANTOS SILVA ET AL: "Paraquat-loaded alginate/chitosan nanoparticles: Preparation, characterization and soil sorption studies", JOURNAL OF HAZARDOUS MATERIALS, vol. 190, no. 1-3, 1 June 2011 (2011-06-01), AMSTERDAM, NL, pages 366 - 374, XP055672453, ISSN: 0304-3894, DOI: 10.1016/j.jhazmat.2011.03.057 *
RAMIN KHAKSAR ET AL: "Nisin-loaded alginate-high methoxy pectin microparticles: preparation and physicochemical characterisation", INTERNATIONAL JOURNAL OF FOOD SCIENCE AND TECHNOLOGY., vol. 49, no. 9, 17 March 2014 (2014-03-17), GB, pages 2076 - 2082, XP055672450, ISSN: 0950-5423, DOI: 10.1111/ijfs.12516 *
See also references of EP3897155A1

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022118019A1 (en) 2020-12-01 2022-06-09 Pangaea Agrochemicals Limited Reduced surfactant pesticide formulations
IT202100002042A1 (en) 2021-02-01 2022-08-01 Ndg Natural Dev Group S R L HERBICIDAL COMPOSITION

Also Published As

Publication number Publication date
CA3124041A1 (en) 2020-06-25
PH12021551727A1 (en) 2022-04-11
CN113473862A (en) 2021-10-01
ZA202105017B (en) 2025-05-28
CO2021009336A2 (en) 2021-10-29
KR20210123303A (en) 2021-10-13
CN113473862B (en) 2023-06-02
IL284105A (en) 2021-08-31
MX2021007407A (en) 2021-09-23
JP7475066B2 (en) 2024-04-26
IL284105B1 (en) 2024-07-01
CR20210391A (en) 2021-10-19
IL284105B2 (en) 2024-11-01
KR102918251B1 (en) 2026-01-26
EP3897155A1 (en) 2021-10-27
JP2022516034A (en) 2022-02-24
AU2019409025B2 (en) 2025-08-28
MA54535A (en) 2022-03-30
AU2019409025A1 (en) 2021-08-12
ECSP21053984A (en) 2021-09-30
MY207908A (en) 2025-03-27
GB2586771A (en) 2021-03-10
US20220071202A1 (en) 2022-03-10
BR112021012147A2 (en) 2021-09-28
GB201821031D0 (en) 2019-02-06

Similar Documents

Publication Publication Date Title
CN108935456A (en) A kind of pesticide synergistic agent and its application in Herbicidal combinations, Pesticidal combination and bactericidal composition
AU2019409025B2 (en) Encapsulated pesticide
AU2009230768A1 (en) Physical Mode of Action Pesticide
CN101416631A (en) Functional slow-release suspension seed-coating agents
EP1742728A1 (en) Microbial encapsulation
EP0719500B1 (en) Solid glyphosate formulations
CN102172250A (en) Preparation method and application of eauveria-spinosad suspending agent
CN114342951B (en) Composite nanoparticles that accelerate the degradation of pesticide residues and their preparation methods and applications
EP3648598A1 (en) Encapsulated pesticide
CN102204529A (en) Lythidathion microcapsule suspension and preparation method thereof
CN102630666B (en) Emulsion-in-water insecticide and production process thereof
CN110037014B (en) Compound synergist containing lecithin and D-limonene and preparation method and application thereof
RU2850828C2 (en) Encapsulated pesticide
CN107646838A (en) A kind of edible glue class pesticide spray assistant composition
BR112021012147B1 (en) METHOD FOR ENCAPSULATING A PESTICIDE AND METHODS FOR APPLYING AN ENCAPSULATED PESTICIDE TO A PLANT
CN107156158A (en) A kind of seed treatment compositions containing pyraclostrobin, fluopyram and ethiprole
CN104255746A (en) Botanical insecticide composition and preparation method thereof
CN106431735A (en) Insect-resistant quick-acting fruit tree complex leaf fertilizer and preparation method thereof
CN106577868A (en) Plant-sourced insect-resistant foliar fertilizer additive and preparation method thereof
WO2024149991A1 (en) Agrochemical compositions
FR2588442A1 (en) Rice seeds coated with algicide and process for growing rice
CN109874784A (en) A kind of preparation method of plant extract pesticide residue-free pesticide
GB2626306A (en) Agrochemical compositions
CN106565322A (en) Chelating plant source insect-damage-resistant leaf fertilizer and preparation method thereof
CN119073308A (en) A method for preparing chitosan oligosaccharide drug-loaded microcapsules

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 19839120

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 3124041

Country of ref document: CA

WWE Wipo information: entry into national phase

Ref document number: MX/A/2021/007407

Country of ref document: MX

ENP Entry into the national phase

Ref document number: 2021536391

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

REG Reference to national code

Ref country code: BR

Ref legal event code: B01A

Ref document number: 112021012147

Country of ref document: BR

WWE Wipo information: entry into national phase

Ref document number: NC2021/0009336

Country of ref document: CO

ENP Entry into the national phase

Ref document number: 2019839120

Country of ref document: EP

Effective date: 20210721

ENP Entry into the national phase

Ref document number: 2019409025

Country of ref document: AU

Date of ref document: 20191220

Kind code of ref document: A

ENP Entry into the national phase

Ref document number: 112021012147

Country of ref document: BR

Kind code of ref document: A2

Effective date: 20210618

WWP Wipo information: published in national office

Ref document number: MX/A/2021/007407

Country of ref document: MX

WWP Wipo information: published in national office

Ref document number: NC2021/0009336

Country of ref document: CO

WWG Wipo information: grant in national office

Ref document number: 2021121495

Country of ref document: RU

WWG Wipo information: grant in national office

Ref document number: MX/A/2021/007407

Country of ref document: MX