WO2013059288A1 - Formulations stables contenant de l'oxyde d'aluminium fumé - Google Patents

Formulations stables contenant de l'oxyde d'aluminium fumé Download PDF

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Publication number
WO2013059288A1
WO2013059288A1 PCT/US2012/060571 US2012060571W WO2013059288A1 WO 2013059288 A1 WO2013059288 A1 WO 2013059288A1 US 2012060571 W US2012060571 W US 2012060571W WO 2013059288 A1 WO2013059288 A1 WO 2013059288A1
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WO
WIPO (PCT)
Prior art keywords
composition
agent
grams
suspoemulsion
atrazine
Prior art date
Application number
PCT/US2012/060571
Other languages
English (en)
Inventor
Timothy Martin
Original Assignee
Fmc Corporation
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 Fmc Corporation filed Critical Fmc Corporation
Priority to JP2014537170A priority Critical patent/JP5964441B2/ja
Priority to KR1020147013034A priority patent/KR101931846B1/ko
Priority to CA2852240A priority patent/CA2852240A1/fr
Priority to MX2014004697A priority patent/MX351568B/es
Priority to AU2012326246A priority patent/AU2012326246B2/en
Priority to CN201280051258.3A priority patent/CN103957718B/zh
Priority to US14/351,974 priority patent/US8962525B2/en
Publication of WO2013059288A1 publication Critical patent/WO2013059288A1/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
    • A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
    • A01N43/68—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms directly attached to ring carbon atoms
    • A01N43/70—Diamino—1,3,5—triazines with only one oxygen, sulfur or halogen atom or only one cyano, thiocyano (—SCN), cyanato (—OCN) or azido (—N3) group directly attached to a ring carbon atom
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Definitions

  • the present invention relates to the field of agrochemical formulations.
  • compositions containing two or more herbicides are desirable in agricultural, specialty applications and related endeavors due to broadening the spectrum or range of unwanted plant species killed or controlled.
  • Tank mixing In which the ingredients in their commercially available form are mixed together by the user in a quantity of water. Tank mixes require the end user to purchase two or more commercial formulations, store them, calculate the correct amount of each active ingredient, measure those amounts into the mix and when empty, properly dispose of a number of containers.
  • Tank mixing two or three different commercial formulations often results in physical instabilities causing precipitation of active ingredients, flocculation, phase separation and the like, providing uneven distribution of the active ingredients.
  • Combining active ingredients into one formulation is beneficial but frequently more complex due to widely different physical properties of the active ingredients in which chemical and physical stability are problems.
  • the present invention relates to a novel aqueous suspoemulsion composition containing an herbicidal agent comprised of atrazine, pyroxasulfone and fluthiacet-methyl that has superior chemical and physical stability as well as superior re-dispersion.
  • Still another embodiment of the present invention is a process for the preparation of an aqueous suspoemulsion composition
  • a process for the preparation of an aqueous suspoemulsion composition comprising:
  • Another embodiment of the present invention is an aqueous suspension concentrate composition
  • aqueous suspension concentrate composition comprising:
  • an agriculturally active component comprising fluthiacet-methyl, atrazine and pyroxasulfone
  • a surfactant component comprising an acrylic graft copolymer and a
  • fumed alumina provides exceptional physical and chemical stability to the compositions.
  • Other stabilizing agents for example, fumed silica, when used in the present suspoemulsion or suspension concentrate compositions, provide good chemical stability but lack physical stability (e.g. precipitates form after 24 hours at room temperature, re-dispersion difficulties).
  • Adding fumed alumina to the present suspoemulsion or suspension concentrate compositions provides chemically and physically stable compositions.
  • fumed alumina can be added to the suspension concentrate composition portion, or may be added to the final formulation composition; preferably it is added to the suspension concentrate portion of the composition.
  • a suspoemulsion composition is formed by combining a suspension concentrate composition with an emulsion in water composition.
  • a suspension concentrate (SC) is a formulation in which a solid active ingredient(s) is suspended in a liquid carrier.
  • the aqueous suspension concentrate composition portion of the suspoemulsion further comprises a surfactant component, a pH adjuster (optional), an anti-freeze agent, an antifoam agent and an anti-microbial (biocide) agent.
  • Atrazine is present in an amount of from 40% to 55% by weight, preferably in an amount of from 44% to 51% by weight of all the components in the SC composition.
  • An emulsion in water is a formulation in which droplets of a non-water soluble phase (oil or non-water soluble solvent) is evenly distributed in water.
  • the EW portion of the suspoemulsion composition of the present invention further comprises a solvent that is not water soluble, a surfactant component, a pH adjuster, an anti-freeze agent, an antifoam agent and an anti-microbial (biocide) agent.
  • Fluthiacet- methyl is present in an amount of 1% to 2% by weight of all the components in the EW composition.
  • the solvent is preferably an aromatic solvent, for example, Aromatic 200 or Aromatic 200 ND, available from ExxonMobilTM Chemicals, and is present in an amount of from 45% to 50% by weight of all the components in the EW composition.
  • the surfactant component is comprised of at least two surfactants; a non-ionic polymeric surfactant and a polyalkylene oxide block copolymer.
  • the non-ionic polymeric surfactant is preferably, for example, AtloxTM 4914, available from Crodia Crop Care and is present in an amount of from 4% to 5% by weight of all the components in the EW composition.
  • polyalkylene oxide block copolymer is preferably, for example, AtlasTM G-5000, available from Crodia Crop Care and is present in amount of from 4.5% to 5.5% by weight of all the components in the EW composition.
  • the pH adjuster is preferably an acid, for example, glacial acetic acid, and is present in an amount of from 0.01% to 0.1 % by weight of all the components in the EW composition.
  • the anti-freeze agent is preferably propylene glycol and is present in an amount of from 5% to 10% by weight, preferably 6% by weight of all the components in the EW composition.
  • the antifoam agent is preferably a silicone emulsion, for example,
  • DOWCORNING ® AF Emulsion available from Dow ® Chemical Company and is present in an amount of 0.05% to 0.5% by weight, preferably 0.1% by weight of all the components in the EW composition.
  • the biocide is preferably, for example, KATHONTM CG or LEGEND ® MK both available from Dow ® Chemical Company or Acticide ® MV available from Thor Specialties, Inc. and is present in an amount of from 0.05% to 0.1% by weight of all the components in the EW composition.
  • an aqueous suspension concentrate is formed using fumed alumina as the stability agent.
  • the aqueous suspension concentrate composition comprises an active ingredient component comprising fluthiacet-methyl, pyroxasulfone and atrazine; a surfactant component comprising an acrylic graft copolymer and a polyalkylene oxide copolymer; an antifoam agent; a biocide; a pH adjusting agent; an antifreeze agent; and a stabilization agent.
  • Fluthiacet-methyl is present in an amount of from 0.1% to 0. 2% by weight of all the components in the SC composition.
  • Pyraxosulfone is present in an amount of from 5% to 7% by weight of all the components in the SC
  • the pH adjuster is preferably an acid, for example, glacial acetic acid, and is present in an amount of from 0.01% to 0.1% by weight of all the components in the SC composition.
  • the anti-freeze agent is preferably propylene glycol and is present in an amount of from 5% to 10% by weight, preferably 5.5% to 6% by weight of all the components in the SC composition.
  • the antifoam agent is preferably a silicone emulsion, for example, DOWCORNING ® AF Emulsion available from Dow ® Chemical Company and is present in an amount of 0.05% to 0.1% by weight of all the components in the SC composition.
  • the biocide is preferably, for example, KATHONTM CG or
  • LEGEND ® MK both available from Dow ® Chemical Company or Acticide ® MV available from Thor Specialties, Inc., and is present in an amount of from 0.01% by weight to 0.1% by weight of all components in the total composition.
  • the stabilization component is fumed alumina, preferably as an aqueous dispersion that is acidic, for example, AERODISP® W 630, available from Evonik Industries, and is present in an amount of from 0.5% to 2% by weight of all the components in the SC composition.
  • the weight ratio of fluthiacet-methyl to pyraxosulfone to atrazine can vary over a wide range but is usually in the range of 1:33:284 to 1:40:325.
  • a particular embodiment of the present invention is a method for the control of unwanted plants comprising applying a pesticidally effective amount of the composition of the present invention to an area where such control is desired.
  • ambient temperature and "room temperature” as utilized herein shall generally mean any suitable temperature found in a laboratory or other working quarter, and is generally neither below about 15° C nor above about 30° C.
  • by weight of components in the composition includes the wt % of all liquid and solid components in the composition.
  • a suspoemulsion concentrate was formed by combining 367.82 grams of atrazine/pyroxasulfone SC from Step A with 51.84 grams of the fluthiacet-methyl EW from Step B and 4.67 grams of deionized water. The resultant composition was stirred until a uniform mixture was obtained. The resultant suspoemulsion concentrate composition was evenly distributed into eight ounce glass jars, sealed and stored for stability testing either at an elevated temperature of 54° C for two weeks.
  • SC Atrazine/Pyroxasulfone Suspension Concentrate
  • EW Fluthiacet-methyl emulsion in Water
  • Tersp 2500 Tersperse® 2500 from Huntsman Performance Products
  • Thickener Veegum® Magnesium Aluminum Silicate from R.T. Vanderbilt Company Inc.
  • Atlox AtloxTM 4914 from Crodia Crop Care
  • Thickener Kelzan® ASX Xanthan Gum form CPKelco A Huber Company
  • Step A Atrazine/Pyroxasulfone Suspension Concentrate (SC)
  • Portion wise additions of pyroxasulfone (480.0 grams, 99.3% purity) and Atrazine (3.862.0 kilograms, 97.0% purity) were made to the tank allowing each addition to mix in thoroughly before adding the next portion.
  • the mixture was transferred to an attritor mill and milled, keeping the temperature at less than 30°C, until a particle size of D90 ⁇ 3 ⁇ was attained.
  • the milled mixture was transferred to a blending tank and 138.9 grams of an aqueous dispersion of fumed alumina (Aerodisp ® W630 from Evonic Industries) was added. The mixture was stirred for one hour to provide 6.79 kilograms of a suspension concentrate.
  • Step B Fluthiacet- methyl Emulsion in Water (EW)
  • An organic phase was prepared by adding 141.4 grams of fluthiacet-methyl (99.1% purity) and 544.5 grams of a nonionic polymeric surfactant (AtloxTM 4914 from Crodia Crop Care) to 5.4446 kilograms of an aromatic naphthalene depleted solvent (Aromatic 200 ND from ExxonMobil Chemicals). The mixture was stirred and heated to about 55°C, in a 15 liter jacketed vessel with an in-line homogenizer, forming a solution.
  • a nonionic polymeric surfactant AtloxTM 4914 from Crodia Crop Care
  • An aqueous phase was prepared by adding 5.7 grams of glacial acetic acid, 687.7 grams of propylene glycol, 573.1 grams of a polyalkylene oxide block copolymer (AtlasTM G5000 from Crodia Crop Care), 5.70 gram of anti foam agent (Dow ® Antifoam AF from The Dow Chemical Company) and 4.0492 kilograms of deionized water into a mixing vessel and heated at 55°C until a homogenous mixture was obtained.
  • the warm organic phase was added to the aqueous phase through the recirculation line of an in-line homogenizer. Once the addition was complete, the homogenization continued until a particle size of less than 3 microns at D90 was achieved.
  • the mixture was allowed to cool to room temperature and 10.3 grams of a preservative (Acticide ® MV from Thor Specialties, Inc.) was added and stirred until a uniform mixture, about 11.2 kilograms, was obtained.
  • a suspoemulsion concentrate was formed by combining 6.658 kiolgrams grams of atrazine/pyroxasulfone SC from Step A with 941.0 grams of the fluthiacet- methyl EW from Step B and 186.0 grams of deionized water. The resultant composition was stirred until a uniform mixture, 7.77 kilograms, was obtained. This suspoemulsion formulation was stored in separate sealed glass containers.
  • a suspoemulsion concentrate was formed by combining 449.3 grams of atrazine/pyroxasulfone SC from Step A with 50.8 grams of the fluthiacet-methyl EW from Step B and 4.67 grams of deionized water. The resultant composition was stirred until a uniform mixture was obtained. This suspoemulsion formulation was stored in separate sealed glass containers.
  • Example 3 and Example 4 were analyzed for physical and chemical stability at 24hours (Initial), Freeze/Thaw (F/T) cycle (three cycles of two days at minus 30°C/two days at room temperature) and 54°C for two weeks.
  • the suspoemulsion of Example 3 was also analyzed for physical and chemical stability at one and three months at 50°C and one month at room temperature. Sample viscosity (centipoise) was measured using a Brookfield RVT viscometer, spindle number 3, spindle speed of 50.
  • Particle size was measured using a particle size distribution analyzer (Horiba Particle Scattering Particle Size Distribution Analyzer LA-910) at D90 (90% of the particles were of the size reported in microns). Percent separation was measured visually by measuring the height of the separated layer and dividing that number by the total height of the container. Analysis for the active ingredients was performed by HPLC analysis on a % by weight basis. These data are summarized in Table 4B below. Table 4B
  • compositions are formed by the addition of fumed alumina to agricultural compositions such as suspoemulsion formulations and suspension concentrate formulations as compared to similar compositions employing commonly used stabilizers such as fumed silica.

Abstract

L'invention concerne de nouvelles compositions herbicides d'une suspo-émulsion aqueuse ou d'un concentré de suspension aqueuse contenant un agent actif herbicide et de l'alumine fumée comme agent stabilisant, et qui présentent une stabilité chimique et physique supérieure ainsi que des propriétés supérieures de redispersion.
PCT/US2012/060571 2011-10-18 2012-10-17 Formulations stables contenant de l'oxyde d'aluminium fumé WO2013059288A1 (fr)

Priority Applications (7)

Application Number Priority Date Filing Date Title
JP2014537170A JP5964441B2 (ja) 2011-10-18 2012-10-17 フュームド酸化アルミニウムを含む安定な調合物
KR1020147013034A KR101931846B1 (ko) 2011-10-18 2012-10-17 흄드 산화 알루미늄을 함유하는 안정한 제제
CA2852240A CA2852240A1 (fr) 2011-10-18 2012-10-17 Formulations stables contenant de l'oxyde d'aluminium fume
MX2014004697A MX351568B (es) 2011-10-18 2012-10-17 Formulaciones estables que contienen oxido de aluminio ahumado.
AU2012326246A AU2012326246B2 (en) 2011-10-18 2012-10-17 Stable formulations containing fumed aluminum oxide
CN201280051258.3A CN103957718B (zh) 2011-10-18 2012-10-17 包含气相氧化铝(fumed aluminum oxide)的稳定制剂
US14/351,974 US8962525B2 (en) 2011-10-18 2012-10-17 Stable formulations containing fumed aluminum oxide

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201161548273P 2011-10-18 2011-10-18
US61/548,273 2011-10-18

Publications (1)

Publication Number Publication Date
WO2013059288A1 true WO2013059288A1 (fr) 2013-04-25

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Application Number Title Priority Date Filing Date
PCT/US2012/060571 WO2013059288A1 (fr) 2011-10-18 2012-10-17 Formulations stables contenant de l'oxyde d'aluminium fumé

Country Status (7)

Country Link
JP (1) JP5964441B2 (fr)
KR (1) KR101931846B1 (fr)
CN (1) CN103957718B (fr)
AU (1) AU2012326246B2 (fr)
CA (1) CA2852240A1 (fr)
MX (1) MX351568B (fr)
WO (1) WO2013059288A1 (fr)

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CN104094945A (zh) * 2014-06-25 2014-10-15 广东中迅农科股份有限公司 一种玉米田除草剂
CN106028810A (zh) * 2014-02-28 2016-10-12 组合化学工业株式会社 茎叶处理用农药组合物
WO2019072602A1 (fr) * 2017-10-09 2019-04-18 Basf Se Nouvelles compositions agrochimiques pesticides

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CN106259362A (zh) * 2015-06-09 2017-01-04 江苏龙灯化学有限公司 一种增效除草组合物
CN111132804A (zh) 2017-08-31 2020-05-08 川崎重工业株式会社 把持装置
CN107509733A (zh) * 2017-09-12 2017-12-26 河南省农业科学院植物保护研究所 一种含有莠去津和砜吡草唑的玉米田除草组合物

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CN106028810A (zh) * 2014-02-28 2016-10-12 组合化学工业株式会社 茎叶处理用农药组合物
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CN104094945A (zh) * 2014-06-25 2014-10-15 广东中迅农科股份有限公司 一种玉米田除草剂
WO2019072602A1 (fr) * 2017-10-09 2019-04-18 Basf Se Nouvelles compositions agrochimiques pesticides
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CN111200934B (zh) * 2017-10-09 2022-12-20 巴斯夫欧洲公司 新型农业化学农药组合物

Also Published As

Publication number Publication date
CN103957718A (zh) 2014-07-30
KR101931846B1 (ko) 2018-12-21
MX351568B (es) 2017-10-19
CN103957718B (zh) 2017-10-24
JP2014530252A (ja) 2014-11-17
AU2012326246A1 (en) 2014-05-01
AU2012326246B2 (en) 2015-09-17
KR20140079483A (ko) 2014-06-26
CA2852240A1 (fr) 2013-04-25
MX2014004697A (es) 2014-10-17
JP5964441B2 (ja) 2016-08-03

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