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WO2018195582A1 - Formulation herbicide - Google Patents

Formulation herbicide Download PDF

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Publication number
WO2018195582A1
WO2018195582A1 PCT/AU2018/000060 AU2018000060W WO2018195582A1 WO 2018195582 A1 WO2018195582 A1 WO 2018195582A1 AU 2018000060 W AU2018000060 W AU 2018000060W WO 2018195582 A1 WO2018195582 A1 WO 2018195582A1
Authority
WO
WIPO (PCT)
Prior art keywords
formulation
imazapic
hexazinone
unwanted vegetation
effective amount
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/AU2018/000060
Other languages
English (en)
Inventor
Andrew HORSFIELD
Peter Henry VAUGHAN
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.)
Adama Australia Pty Ltd
Original Assignee
Adama Australia Pty 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 claimed from AU2017901511A external-priority patent/AU2017901511A0/en
Application filed by Adama Australia Pty Ltd filed Critical Adama Australia Pty Ltd
Priority to AU2018259149A priority Critical patent/AU2018259149B2/en
Publication of WO2018195582A1 publication Critical patent/WO2018195582A1/fr
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
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles

Definitions

  • the invention described herein relates to an herbicidal formulation.
  • the invention is directed to a formulation for an herbicide which includes as active ingredients imazapic (5-methyl-2-(4-methyl-5-oxo-4-propan-2-yl- 1 H-imidazol-2-yl) pyridine-3-carboxylic acid) and hexazinone (3-cyclohexyl-6-(dimethylamino)-l-methyl- 1 ,3,5-triazine-2,4-dione).
  • Agricultural chemical products such as herbicides can undergo chemical and physical changes during storage.
  • the rate at which these changes occur may depend on the nature of the components, the formulation type, the packaging and, notably, the storage conditions, including temperature, light and humidity.
  • the product may remain fit for use as long as these changes have no adverse effects on application, biological performance, and the safety of operators, consumers and environment. However, in some cases degradation of the active ingredient may occur, reducing efficacy and/or shelf life.
  • SL formulations for herbicides available on the market include propylene carbonate and water, which react to produce small amounts of carbon dioxide on storage, or may contain flammable solvents such as methanol.
  • the emission of C0 2 results in the need to use a vented cap to prevent swelling of the storage containers and possible leakage of contents. It has also been found that, with the emission of C0 2; crystals may form in the soluble concentrate.
  • the flammability creates greater risk for production, transport, storage and application of the herbicide. It is an aim of the invention to provide a formulation which overcomes or ameliorates one or more of the disadvantages or problems described above, or which at least provides a useful choice.
  • SL soluble concentrate
  • the formulation of the invention may include about 2% to 3% of imazapic. Accordingly, the effective amount of imazapic may be about 22.5 to 27.5 g/L, and preferably about 25 g/L.
  • the formulation may include 12% to 13% hexazinone. Accordingly, the effective amount of hexazinone may be about 1 18 - 132 g/L and preferably about 125 g/L.
  • the formulation of the invention contains imazapic: hexazinone in the ratio range of 1 : 4 to 1 : 5.
  • Other ratio ranges may also be applicable, particularly if the formulation of the invention contains one or more further active ingredients.
  • the formulation may have a ratio of 1 :2 in those circumstances.
  • the solvent may be any suitable solvent but is preferably an N-alklyenepyrrolidine solvent. It may include an effective amount of l-methylpyrrolidin-2-one. The solvent may include an effective amount of l -butylpyrrolidin-2-one. The solvent may include a combination of l-methylpyrrolidin-2-one and l-butylpyrrolidin-2-one. In particular, the formulation may include 10% to 11% l-methylpyiTolidin-2-one, and 19% to 20% 1- butylpyrrolidin-2-one.
  • the herbicidal formulation of the invention is in the form of a soluble concentrate (SL).
  • SL soluble concentrate
  • Herbicides in the form of powder or granules require handling before mixing with water until the solids dissolve before use. As herbicides can often contain toxic substances, the manual handling of herbicides in these circumstances can present a health and safety hazard, and lead to spillage and contamination.
  • SL formulations typically only require dilution before use, and can be safer to use.
  • the formulation of the invention has a pH balance of less than 7.
  • the formulation of the invention may include one or more buffering agents.
  • a buffering agent may be potassium dihydrogen phosphate.
  • a buffering agent may be acetic acid.
  • the formulation may include 1% to 2% of potassium dihydrogen phosphate.
  • the formulation may further include 1 to 2% of acetic acid.
  • the formulation may further include water, such as 50% to 60% deionised water.
  • a method for controlling unwanted vegetation comprises applying an effective amount of a formulation as described above to the unwanted vegetation, to parts of the unwanted vegetation, to seeds of the unwanted vegetation or to the area on which the unwanted vegetation grows.
  • the method of the invention is used to control unwanted vegetation in sugarcane and other crops.
  • the method may also be used to manage unwanted vegetation, especially weeds, in other situations.
  • An example is weed management in industrial settings, such as wastelands, around buildings, along fence lines and along railway lines.
  • Table 1 Imazapic - Hexazinone co-formulation
  • the formulation can be manufactured in two parts (Part I and Part II).
  • an imazapic ammonium salt solution is prepared.
  • the constituents of the imazapic ammonium salt solution are provided in Table 2 below.
  • the imazapic ammonium salt solution is prepared using a suitable vessel equipped with a stirrer, by first adding Part A of the water and then whilst stirring adding the urea. Whilst continuing to stir, monopotassium phosphate is added, followed by imazapic technical.
  • ammonia solution is then charged and stirring is continued until all of the imazapic has completely reacted and dissolved. Whilst the ammonia solution is nominally 28%, the concentration can vary from 10 - 35%. The quantity required for a complete reaction (dissolution) of the imazapic technical is adjusted. Excess ammonia solution, as indicated by neat pH at this point which must not exceed 9.0, should be avoided.
  • Citric acid is then carefully added until the neat pH is brought into the range 7.0 - 7.5.
  • the imazapic ammonium salt solution (Part I) is put aside and ready for subsequent addition to the hexazinone solution (Part II), prepared as set out below.
  • Part II a hexazinone solution is prepared and subsequently combined with the imazapic ammonium salt solution prepared in Part I above.
  • the constituents of the hexazinone solution are provided in Table 3 below.
  • the hexazinone solution is prepared in a suitable vessel equipped with a stirrer, by first adding Part B of the water. Whilst stirring, NMP is added, followed by Genagen NBP. As stirring continues, hexazinone technical is added. Stirring is continued for a further 30 minutes until hexazinone technical is completely dissolved. Whilst continuing to stir, the previously prepared imazapic ammonium salt solution (Part I) is charged and combined with the hexazinone solution (Part II). Stirring is continued for a further 10 minutes. The content of the active ingredients is tested and can be adjusted as required. The formulation is a clear pale yellow liquid having a pH balance of less than 7. The pH balance of a tested formulation sample (1% v/v dilution) was 6.73.
  • the content of the imazapic ranges between 22.5 to 27.5 g/L
  • the content of Hexazinone ranges between 118 - 132 g/L.
  • Testing revealed the content of the active ingredients for the formulation produced using the above method was 26.5 g/L for imazapic, and 127 g/L for hexazinone.
  • the formulation according to the present invention can be stored in a standard high density polyethylene (HDPE) capped bottle, without the need for venting.
  • HDPE high density polyethylene
  • the sample was then placed into a thermostatically controlled oven (VWR Mini Incubator: SNR 0811 VI 169, sourced from VWR, now Avantor of Radford, PA, USA) and 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 0811 VI 169, sourced from VWR, now Avantor of Radford, PA, USA
  • Imazapic and hexazinone were determined by reversed phase, high performance liquid chromatography (HPLC), using UV detection and external standardisation.
  • the formulation described above can be stored in a standard HDPE bottle without any ventilation. Test results show that the formulation will remain stable for extended periods of storage without C0 2 emission.
  • the herbicide formulation of the invention provides a combination of imazapic and hexazinone which exhibits stability and which can be stored in standard packaging without the need for packaging ventilation.

Landscapes

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

Abstract

L'invention concerne une formulation herbicide qui comprend de l'hexazinone et de l'imazapic, ces derniers sous la forme de l'urée ou du sel d'ammonium ou d'une de leurs combinaisons. La formulation est un concentré soluble (SL) et comprend également un solvant. La formulation est sensiblement exempte de carbonate d'alkylène et de méthanol.
PCT/AU2018/000060 2017-04-26 2018-04-24 Formulation herbicide Ceased WO2018195582A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU2018259149A AU2018259149B2 (en) 2017-04-26 2018-04-24 Herbicidal formulation

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
AU2017901511 2017-04-26
AU2017901511A AU2017901511A0 (en) 2017-04-26 Herbicidal Formulation

Publications (1)

Publication Number Publication Date
WO2018195582A1 true WO2018195582A1 (fr) 2018-11-01

Family

ID=63917782

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/AU2018/000060 Ceased WO2018195582A1 (fr) 2017-04-26 2018-04-24 Formulation herbicide

Country Status (3)

Country Link
AR (1) AR111415A1 (fr)
AU (1) AU2018259149B2 (fr)
WO (1) WO2018195582A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109738558A (zh) * 2019-01-10 2019-05-10 黄志勇 花生仁中甲咪唑烟酸残留量的定量测定方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009054823A2 (fr) * 2007-10-23 2009-04-30 E. I. Du Pont De Nemours And Company Mélange d'herbicides, procédé pour lutter contre la végétation indésirable et utilisation des herbicides
WO2015078243A1 (fr) * 2013-11-28 2015-06-04 Rotam Agrochem International Company Limited Compositions herbicides comprenant un herbicide à base de triazinone et un herbicide inhibiteur de l'als, et utilisations de celles-ci
US20160213000A1 (en) * 2013-09-26 2016-07-28 Basf Agrochemical Products B.V. Method for Controlling Weeds in Sugar Cane Plantations
US20160270401A1 (en) * 2013-02-22 2016-09-22 Ishihara Sangyo Kaisha, Ltd. Herbicidal composition

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009054823A2 (fr) * 2007-10-23 2009-04-30 E. I. Du Pont De Nemours And Company Mélange d'herbicides, procédé pour lutter contre la végétation indésirable et utilisation des herbicides
US20160270401A1 (en) * 2013-02-22 2016-09-22 Ishihara Sangyo Kaisha, Ltd. Herbicidal composition
US20160213000A1 (en) * 2013-09-26 2016-07-28 Basf Agrochemical Products B.V. Method for Controlling Weeds in Sugar Cane Plantations
WO2015078243A1 (fr) * 2013-11-28 2015-06-04 Rotam Agrochem International Company Limited Compositions herbicides comprenant un herbicide à base de triazinone et un herbicide inhibiteur de l'als, et utilisations de celles-ci

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
ADAMA AUSTRALIA PTY LIMITED: "BOBCAT I-MAXX HERBICIDE, Soluble Concentrate", AUSTRALIAN PESTICIDES AND VETERINARY MEDICINES AUTHORITY, 10 February 2015 (2015-02-10), XP055526767 *
FARMOZ PTY LIMITED: "Application Summary for Application No 61461, Bobcat i- MAXX Herbicide", AUSTRALIAN PESTICIDES & VETERINARY MEDICINES AUTHORITY (APVMA), 27 March 2014 (2014-03-27), XP055526776, Retrieved from the Internet <URL:http://archive.apvma.gov.au/application_summaries/61461.pdf> *

Also Published As

Publication number Publication date
AU2018259149A1 (en) 2019-12-19
AR111415A1 (es) 2019-07-10
AU2018259149B2 (en) 2024-06-13

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