WO2023023813A1 - Amélioration apportée à des formulations de concentré en suspension - Google Patents

Amélioration apportée à des formulations de concentré en suspension Download PDF

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Publication number
WO2023023813A1
WO2023023813A1 PCT/AU2022/051041 AU2022051041W WO2023023813A1 WO 2023023813 A1 WO2023023813 A1 WO 2023023813A1 AU 2022051041 W AU2022051041 W AU 2022051041W WO 2023023813 A1 WO2023023813 A1 WO 2023023813A1
Authority
WO
WIPO (PCT)
Prior art keywords
formulation
epoxiconazole
particle size
size distribution
less
Prior art date
Application number
PCT/AU2022/051041
Other languages
English (en)
Inventor
Andrew HORSFIELD
Peter Vaughan
Original Assignee
Adama Australia Pty Limited
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
Application filed by Adama Australia Pty Limited filed Critical Adama Australia Pty Limited
Priority to AU2022333660A priority Critical patent/AU2022333660A1/en
Publication of WO2023023813A1 publication Critical patent/WO2023023813A1/fr

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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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • 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
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P3/00—Fungicides

Definitions

  • the invention relates to suspension concentrate formulations.
  • the invention also relates to highly loaded epoxiconazole formulations incorporating the suspension concentrate aspect of the invention.
  • a suspension concentrate is commonly used for formulations where one or more of the active ingredients is sparingly soluble in water or in organic solvents.
  • An SC is a dispersion of small particles. Generally, the particles have a diameter in the range 0.4-12 pm. Particles may be attracted to each other, causing flocculation or settling, making the SC unstable.
  • Epoxiconazole (1- ⁇ [3-(2-chlorophenyl)-2-(4-fluorophenyl)oxiran-2"yl]methyl ⁇ -lH-l,2,4-triazole) is a triazole fungicide that inhibits sterol biosynthesis in ascomycete, basidiomycete and deuteromycete fungi.
  • Major use crops for epoxiconazole include cereals, bananas and sugar beet.
  • Epoxiconazole is marketed as both a solo formulation and mixtures in a range of formulation types e.g. emulsifiable concentrates (EC), suspension concentrates (SC), suspoemulsions (SE) and water dispersible granules (WG).
  • the surfactant component disclosed is a comb-graft copolymer surfactant having a poly-methacrylate backbone and pendant polyoxyethylene moieties attached to the backbone, such as that available as Atlox®4913.
  • This component is combined with a second surfactant being either an ethoxylated or a propoxylated fatty alcohol surfactant comprising a fatty alcohol from 12 to 20 carbon atoms, such as that available as Antarox ®65A9P.
  • the particle size distribution disclosed in 2020317060 was Dv (50): 2.07 to 2.14 and Dv (90): 6.01 to 6.10 pm.
  • this invention provides a stable SC formulation which includes an active ingredient which has a particle size distribution in the range Dv (50): more than 4 and less than 5.5 pm and Dv (90): more than 8 and less than 9.8 pm.
  • the particle size distribution may be that measurable prior to and/or after accelerated stability testing.
  • the active ingredient may be chosen from a wide range, not limited to the agrichemical field. However, for the sake of illustration, the disclosure below will describe the invention as applicable to the agrichemical field.
  • the formulation of the invention may include more than one active ingredient.
  • the particle size distribution of the formulation of the invention is within acceptable limits for agricultural chemical products under the APVMA guidelines, referred to in more detail below.
  • the acceptable limits are range Dv (50): less than 5.50 pm and Dv (90): less than 10.0 pm.
  • the particle size distribution relevant to the invention may be regarded as a selection from the acceptable limits. Both the Dv (50) and the Dv (90) distributions are towards the upper end of the acceptable limits.
  • Having a higher particle size distribution has the advantage of requiring less milling of the tech form of the active ingredient, which fine milling is currently required to achieve the initial fine particle size distribution required with existing formulations with of 400 g/L or more.
  • first aspect of the invention is given in the second aspect of the invention - a highly loaded epoxiconazole formulation (see below). It is anticipated that the stable SC formulation of the invention is applicable to many other agricultural formulations.
  • the stable SC formulation of the invention may include other components, including but not limited to dispersants, wetting agents, humectants, rheology modifiers, preservatives and antifoam agents. The choice of these may be made according to the characteristics of the active ingredient/s.
  • the invention provides a stable, highly loaded epoxiconazole SC formulation, wherein the loading of epoxiconazole is more than 400 ai g/L and wherein the particle size distribution of epoxiconazole is in the range Dv (50): more than 4 and less than 5.5 pm and Dv (90): more than 8 and less than 9.8 pm.
  • the formulation contains about 500 ai g/L or more of epoxiconazole.
  • the formulation has a dispersant, being triethanolamine compound with polyoxyethylene tristyrylphenyl ether phosphate-based dispersant, available as Soprophor® FL, for example.
  • a dispersant may be present in a quantity in excess of about 40 g/L or at least about 50 g/L.
  • the formulation includes an ethoxylated isodecyl alcohol wetting agent with a short carbon chain length of 9 to 11 carbon atoms, such as available as Rhodasurf® 860/P, for example.
  • This novel dispersant and surfactant combination provides a high quality alternative option to existing highly loaded epoxiconazole formulations and creates a more shelf stable formulation that is not prone to excessive particle size growth during long term storage.
  • the epoxiconazole formulation may also include all or some of a humectant, a rheology modifier, a preservative and an antifoaming agent.
  • suitable components are propylene glycol as humectant, Rheozan® as rheology modifier, Nipacide® BIT 20 as preservative and Gensil® 030 as antifoaming agent.
  • the viscosity of the formulation is more than about 600 and at least 1000 cps.
  • this embodiment may have nil visible retained material on a 38pm sieve after production and ⁇ 0.05% retained material after accelerated stability testing.
  • This embodiment may also have improved pourability and ⁇ 2% residue and ⁇ 0.1% rinsed residue prior to and after accelerated stability testing.
  • Epoxiconazole was sourced as in Table 2 below: Table 2: Active Ingredient
  • Table 3 Details of the other components are in Table 3: Table 3: Other Components To prepare the formulation, by way of example, the following method and the sequence of operations were followed. The formulation was prepared in a batch process.
  • the specimens remained in their containers and were stored in an air-conditioned facility at approximately 21 °C for the period prior to ambient temperature and elevated temperature storage.
  • the sample designated for elevated temperature storage was placed into a thermostatically controlled oven (VWR Mini Incubator: SNR 0811V1169), heated to 54 ⁇ 2 °C, for a period of 14 days. At the end of this period, the sample was removed from the oven and placed into a desiccation chamber to allow cooling to ambience.
  • VWR Mini Incubator SNR 0811V1169
  • the remaining AD-AU-2006 SC formulation sample (Time Zero sample T01) was stored at air-conditioned ambient temperatures ( ⁇ 21 °C) in a locked cabinet for the duration of the elevated temperature storage period.
  • AD-AU-2006 SC was prepared for low temperature stability testing by placing 100 mL of the formulated product into a 100 mL ASTM D96 graduated centrifuge tube and storing it in a refrigerated cabinet (Esatto Model EBF93W: SNR 5G386) at a temperature of 0 °C ⁇ 2 °C for a total of 7 days. Description of Methods Used
  • the pH value of a 1% v/v dilution of the formulation is determined by means of a pH meter and electrode system.
  • the viscosity of the formulation is measured in a standard measuring system using a Brookfield RV Viscometer.
  • the suspension concentrate is allowed to stand for a definite time and the amount remaining in the container after a standardized pouring procedure is determined.
  • the container is rinsed and the amount then remaining is determined.
  • the method is broadly similar to that used to determine suspensibility (CIPAC MT 184), except that the preparation of the suspension of known concentration employs only one inversion and a 5 min standing time. The top 9/10 ⁇ 5 are the drawn off and the remaining l/10 th is then assayed chemically and the spontaneity of dispersion calculated.
  • a suspension of known concentration in CIPAC Standard Water is prepared, placed in a prescribed measuring cylinder at a constant temperature, and allowed to remain undisturbed for a specific time (30 minutes). The top 9/10 ⁇ 5 are then drawn off and the remaining 1/10 ⁇ is then assayed chemically and the suspensibility calculated.
  • a sample of the formulation is dispersed in water and the suspension formed is transferred to a sieve and washed. The amount of the material retained on the sieve is determined by drying and weighing.
  • a representative sample of the formulation is dispersed in water, and then passed through the beam of a laser.
  • the light scattered by the dispersed particles is measured by a multielement detector.
  • Numerical values relating to the scattering pattern are calculated using an appropriate optical model and mathematical procedure to yield a volumetric particle size distribution.
  • the sample is diluted in a measuring cylinder of standard dimensions which is inverted 30 times and the amount of foam created and remaining after certain times is measured.
  • a sample is maintained at 0 ⁇ 2 °C for 7 days and the nature and quantity of any separated material retained following wet sieving through a 75 pm sieve is determined.
  • Epoxiconazole content is determined by reversed phase high performance liquid chromatography using UV detection and external standardisation.
  • a sample of the product in a container of the same material and construction to that of the marketed product is weighed and then maintained at 54 C for a period of 14 days. Any loss or gain in weight is recorded and the container examined, recording observations of any significant interaction with the formulation.
  • Table 4 below shows analysis at Time Zero
  • Table 5 shows the results of the accelerated stability sample
  • Table 6 shows the result of the cold temperature stability test.
  • the formulation was stable at low temperature.
  • Trial 1 field trial was conducted at Bannockburn, Victoria, to evaluate AD-AU-2006 on stripe rust (Puccinia striiformisf.sp. tritici) in wheat cv. Trojan.
  • AD-AU-2006 was applied twice at 65 and 125 mL/ha as a broadcast application in 125 L/ha volume at BBCH 33 and 39-41.
  • Soprano® 500 was included as the standard fungicide at equivalent epoxiconazole doses.
  • AD-AU-2006 provided similar control and yield improvement compared to the standard formulation, Soprano® 500.
  • Table 7 Stripe rust severity at Bannockburn, Victoria.
  • AD-AU-2006 was applied twice at 65 and 125 mL/ha as a broadcast application in 100 L/ha volume at BBCH 32 and 39.
  • Soprano® 500 was included as the standard fungicide at equivalent epoxiconazole doses.
  • AD-AU-2006 provided similar or superior control of Septoria tritici blotch compared to the standard formulation, Soprano® 500.
  • AD-AU-2006 was applied six times at 75 and 150 mL/ha using a backpack mister.
  • Soprano® was included as the standard fungicide at equivalent epoxiconazole doses.
  • AD-AU-2006 and Soprano® were both tank mixed with Biopest® Oil at 5 L/ha.
  • Solo Biopest® Oil at 5 L/ha was also applied for comparison
  • AD-AU-2006 provided similar or superior control of Yellow Sigatoka compared to the standard formulation, Soprano®.
  • the invention is able to provide an SC formulation containing an active ingredient by choosing large particle size distribution - a counter-intuitive concept to avoid or reduce flocculation - resulting in enhanced stability.

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

Abstract

L'invention concerne une formulation de suspension concentrée stable qui comprend un principe actif qui a une distribution granulométrique dans la plage Dv (50) supérieure à 4 et inférieur à 5,5 μm et Dv (90) supérieure à 8 et inférieure à 9,8 µm. L'invention concerne également une formulation de suspension concentrée d'époxiconazole hautement chargée stable, la charge d'époxiconazole étant supérieure à 400 ai g/L et la distribution granulométrique étant conforme à la plage susmentionnée.
PCT/AU2022/051041 2021-08-25 2022-08-25 Amélioration apportée à des formulations de concentré en suspension WO2023023813A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2022333660A AU2022333660A1 (en) 2021-08-25 2022-08-25 Improvement to suspension concentrate formulations

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
AU2021221775A AU2021221775A1 (en) 2021-08-25 2021-08-25 Improvement to Suspension Concentrate Formulations
AU2021221775 2021-08-25

Publications (1)

Publication Number Publication Date
WO2023023813A1 true WO2023023813A1 (fr) 2023-03-02

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PCT/AU2022/051041 WO2023023813A1 (fr) 2021-08-25 2022-08-25 Amélioration apportée à des formulations de concentré en suspension

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AU (2) AU2021221775A1 (fr)
WO (1) WO2023023813A1 (fr)

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999048359A1 (fr) * 1998-03-20 1999-09-30 Dow Agrosciences Llc Adjuvants pesticides
EP1023832A1 (fr) * 1999-01-29 2000-08-02 American Cyanamid Company Suspension aqueuse concentrée
US20140364308A1 (en) * 2011-12-27 2014-12-11 Sumitomo Chemical Company, Limited Microcapsule containing fungicidal active ingredient
CN109526948A (zh) * 2018-12-28 2019-03-29 苏州佳辉化工有限公司 一种杀菌剂及其制备方法
WO2021012012A1 (fr) * 2019-07-24 2021-01-28 Eureka! Agresearch Pty Ltd Composition fongicide
WO2021127126A1 (fr) * 2019-12-19 2021-06-24 Fmc Corporation Compositions de concentré de suspension de diamide

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999048359A1 (fr) * 1998-03-20 1999-09-30 Dow Agrosciences Llc Adjuvants pesticides
EP1023832A1 (fr) * 1999-01-29 2000-08-02 American Cyanamid Company Suspension aqueuse concentrée
US20140364308A1 (en) * 2011-12-27 2014-12-11 Sumitomo Chemical Company, Limited Microcapsule containing fungicidal active ingredient
CN109526948A (zh) * 2018-12-28 2019-03-29 苏州佳辉化工有限公司 一种杀菌剂及其制备方法
WO2021012012A1 (fr) * 2019-07-24 2021-01-28 Eureka! Agresearch Pty Ltd Composition fongicide
WO2021127126A1 (fr) * 2019-12-19 2021-06-24 Fmc Corporation Compositions de concentré de suspension de diamide

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AU2022333660A1 (en) 2024-04-04
AU2021221775A1 (en) 2023-03-16

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