KR101931846B1 - Stable formulations containing fumed aluminum oxide - Google Patents

Stable formulations containing fumed aluminum oxide Download PDF

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KR101931846B1
KR101931846B1 KR1020147013034A KR20147013034A KR101931846B1 KR 101931846 B1 KR101931846 B1 KR 101931846B1 KR 1020147013034 A KR1020147013034 A KR 1020147013034A KR 20147013034 A KR20147013034 A KR 20147013034A KR 101931846 B1 KR101931846 B1 KR 101931846B1
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composition
atrazine
methyl
rti
suspension concentrate
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KR1020147013034A
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KR20140079483A (en
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티모시 마틴
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에프엠씨 코포레이션
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    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/661,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
    • A01N43/681,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms directly attached to ring carbon atoms
    • A01N43/70Diamino—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
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72Biocides, 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
    • A01N43/80Biocides, 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
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90Biocides, 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

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

Abstract

The present invention provides novel herbicidal suspension emulsions or aqueous suspension concentrate compositions containing herbicidal active agents with excellent chemical and physical stability as well as excellent redispersibility properties and fumed alumina as stabilizers.

Description

[0001] STABLE FORMULATIONS CONTAINING FUMED ALUMINUM OXIDE [0002]

The present invention relates to the field of agrochemical formulations.

In order to efficiently remove or control unwanted plants, it is desirable to use effective chemical agents of herbicides. Compositions containing two or more herbicides are desirable for special applications for agriculture and related efforts since they extend the spectrum or range of unwanted plant species that are killed or controlled.

Since it is desirable to have a composition having the above-mentioned characteristics, it is useful to use a combination of herbicides that promote the control of multiple weeds by applying a single herbicide. Combinations of insecticides are known and are available as a mixed solution of active ingredients in commercially available formulations thereof. One method of making such a composition is referred to as "tank mixing ", and its commercially available form of constituent is mixed with a certain amount of water by the user. Tank mixing allows end-users to purchase more than one commercially available formulation, store it, calculate the exact amount of each active ingredient, quantify and mix the amount of each active ingredient, and dispose of multiple containers when they are empty . Tank mixing of two or three different commercial formulations often results in physical instability causing precipitation, aggregation, phase separation, etc. of the active ingredients, thus providing a non-uniform distribution of active ingredients. While it is advantageous to combine the active ingredients into one preparation, it is often more complicated due to the very different physical properties of the active ingredients, with chemical and physical stability being a problem.

The present invention provides novel herbicidal suspoemulsions or aqueous suspension concentrate compositions containing fumed alumina as a herbicidally active agent and stabilizer with excellent chemical and physical stability as well as excellent redispersion properties .

The present invention provides novel herbicidal suspension emulsions or aqueous suspension concentrate compositions containing herbicidal active agents and fumed alumina as stabilizers, with excellent chemical and physical stability as well as excellent redispersion characteristics.

In one embodiment, the present invention provides a herbicide composition comprising atrazine, pyroxasulfone, and fluthiacet-methyl, which have excellent chemical and physical stability as well as excellent redispersion characteristics To a novel aqueous suspension emulsifier composition.

Specifically, the aqueous suspension emulsifier composition of the present invention comprises:

i) an aqueous suspension concentrate composition comprising a piroxysulfone and atrazine;

ii) an aqueous emulsion composition containing fluthiacet-methyl; And

iii) Fumed alumina.

Another embodiment of the present invention is a compound of formula

i) forming an aqueous suspension concentrate composition comprising a piroxysulfone and atrazine;

ii) forming an aqueous emulsion composition containing fluthiacet-methyl;

iii) blending together the suspension concentrate and the aqueous emulsion composition, and

iv) adding fumed alumina and blending the mixture to form a homogeneous mixture
≪ / RTI >

Another embodiment of the present invention is a compound of formula

i) forming an aqueous suspension concentrate composition containing a pyroxysulfone, atrazine and fumed alumina;

ii) forming an aqueous emulsion composition containing fluthiacet-methyl;

iii) blending together the suspension concentrate and the emulsion composition to form a homogeneous mixture
≪ / RTI >

Another embodiment of the present invention is a compound of formula

i) agricultural active ingredients comprising fluthiacet-methyl, atrazine and pyroxysulfone;

ii) a surfactant component comprising an acrylic graft copolymer and a polyalkylene oxide block copolymer;

iii) defoamer;

iv) biocides;

v) pH adjusting agents;

vi) cryoprotectants; And

vii) Fumed alumina
≪ / RTI >

Surprisingly, it has been found that the addition of fumed alumina to a suspension emulsifier or suspension concentrate composition provides unexpected physical and chemical stability to the composition. Other stabilizers, such as, for example, fumed silica, when used in the suspension emulsifiers or suspension concentrate compositions of the present invention, provide good chemical stability but lack physical stability (e.g., after 24 hours a precipitate forms at room temperature, Difficult to redistribute). Fumed alumina is added to the present suspension emulsifier or suspension concentrate composition to provide a chemically and physically stable composition. In the preparation of the suspension emulsifier composition, the fumed alumina may 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.

In one embodiment of the invention, the suspension emulsifier composition is formed by combining the suspension concentrate composition with an aqueous emulsion composition. Suspended concentrate (SC) is a preparation in which a solid active ingredient is suspended in a liquid carrier. The aqueous suspension concentrate portion of the suspension emulsifier further comprises a surfactant component, a pH adjuster (optional), a cryoprotectant, a defoamer, and an antimicrobial (biocidal) formulation. Atrazine is present in an amount of from 40 wt% to 55 wt%, preferably from 44 wt% to 51 wt%, of all components in the SC composition. The pyroxenes are present in amounts of from 5% to about 7% by weight of all components in the SC composition. The surfactant component is composed of two or more surfactants; Alkyl EO / PO copolymers and acrylic graft copolymers. The alkyl EO / PO copolymer is preferably a TERGITOL XD surfactant, available, for example, from Dow Chemicals and is present in an amount ranging from 2 wt% to 3 wt% of all components in the SC composition % ≪ / RTI > The acrylic graft copolymer is preferably a TERSPERSE 占 2500 dispersant, available, for example, from Huntsman Performance Products, and contains from 3% to 4% by weight of all components in the SC composition, ≪ / RTI > The pH controlling agent is preferably an acid, for example glacial acetic acid, and is present in an amount of 0 to 0.13% by weight of all components in the SC composition. The cryoprotectant is preferably propylene glycol and is present in an amount of 5 wt% to 10 wt%, preferably 6 wt%, of all components in the SC composition. The antifoaming agent is preferably a silicone emulsion and is, for example, a DOWCORNING 占 AF emulsion, available from the Dow Chemical Company, containing from 0.05% to 0.5% by weight of all components in the SC composition, Preferably in an amount of 0.1% by weight. The biocide is preferably selected from the group consisting of, for example, KATHON (R) CG or LEGEND (R) MK or Thor Specialties, Inc., available from Dow Chemical Company. ) And is present in an amount of 0.05 wt.% To 0.5 wt.%, Preferably 0.1 wt.% Of all components in the SC composition. The stabilizing component is preferably a fumed alumina as an acidic aqueous dispersion, for example AERODISP (R) W 630, available from Evonik Industries, And is present in an amount of from 0.5% to 2% by weight. The SC composition comprises a thickener, for example, magnesium aluminum silicate [ (Veegum: < / RTI > magnesium aluminum silicate from R.T. Vanderbilt Company).

An aqueous emulsion (EW) is a preparation in which droplets of a water-insoluble phase (oil or water-insoluble solvent) are uniformly distributed in water. The EW portion of the suspension emulsifier composition of the present invention further comprises a water insoluble solvent, a surfactant component, a pH adjuster, a cryoprotectant, a defoamer, and an antimicrobial agent (biocide). The fluthiacet-methyl is present in an amount of 1 wt% to 2 wt% of all components in the EW composition. The solvent is preferably an aromatic solvent such as Aromatic 200 or Aromatic 200 ND available from ExxonMobil < (R) > Chemicals, from 45% to 50% of all components in the EW composition By weight. The surfactant component is composed of two or more surfactants; Nonionic polymeric surfactants and polyalkylene oxide block copolymers. The nonionic polymeric surfactant is preferably Atlox 4914, available from Crodia Crop Care, for example, from 4 wt% to 5 wt% of all components in the EW composition % ≪ / RTI > The polyalkylene oxide block copolymer is preferably, for example, Atlas (R) G-5000 available from Crodia CropCare, and contains 4.5 wt% to 5.5 wt% of all components in the EW composition Lt; / RTI > The pH adjusting agent is preferably an acid, for example glacial acetic acid, and is present in an amount of 0.01% to 0.1% by weight of all components in the EW composition. The cryoprotectant is preferably propylene glycol and is present in an amount of 5 wt% to 10 wt%, preferably 6 wt%, of all components in the EW composition. The defoamer is preferably a silicone emulsion, for example a Dow Corning (registered trademark) AF emulsion, available from Dow Chemical Company, containing 0.05% by weight to 0.5% by weight, preferably 0.1% by weight Lt; / RTI > The biocide is preferably, for example, Cartis TM CG or Legacy TM MK from Dow Chemical Company or Actide (TM) MV from Tor Specialty Chemicals, Lt; / RTI > by weight of all components in the EW composition.

In another embodiment of the present invention, an aqueous suspension concentrate is formed using fumed alumina as the stabilizer. The aqueous suspension concentrate composition comprises an active ingredient comprising fluthiacet-methyl, pyroxysulfone and atrazine; A surfactant component comprising an acrylic graft copolymer and a polyalkylene oxide copolymer; Defoamer; Biocides; pH adjusting agents; Antifreeze agents; And stabilizers. The fluticaset-methyl is present in an amount of 0.1% to 0.2% by weight of all components in the SC composition. The pyroxenes are present in amounts of from 5% to 7% by weight of all components in the SC composition. Atrazine is present in an amount of from 40% to 45% by weight of all components in the SC composition. The surfactant component is composed of an acrylic graft copolymer and a polyalkylene oxide block copolymer. The acrylic graft copolymer is preferably a Terps (R) 2500 dispersant available, for example, from Huntsman Performance Products, and is present in an amount of 2.5 wt% to 3.0 wt% of all components in the SC composition. The polyalkylene oxide block copolymer is preferably, for example, Atlas G-5000 available from Crodia Crop Care and is present in an amount of from 2.5% to 2.75% by weight of all components in the SC composition do. The pH adjusting agent is preferably an acid, for example glacial acetic acid, and is present in an amount of 0.01% to 0.1% by weight of all components in the SC composition. The cryoprotectant is preferably propylene glycol and is present in an amount of 5 wt% to 10 wt%, preferably 5.5 wt% to 6 wt% of all components in the SC composition. The defoamer is preferably a silicone emulsion, for example a Dow Corning (registered trademark) AF emulsion, available from Dow Chemical Company, and is present in an amount of 0.05% to 0.1% by weight of all components in the SC composition. The biocide is preferably selected, for example, from Carton (registered trademark CG) or Legend (registered trademark) MK from Dow Chemical Company or Actide (registered trademark) MV from Tor Specialty Chemicals , And 0.01% to 0.1% by weight of all components in the total composition. The stabilizing component is preferably a fumed alumina as an acidic aqueous dispersion, for example Aerodisup (R) W 630 available from Econonic Industries, and is present in an amount ranging from 0.5% to 2% by weight % ≪ / RTI >

The weight ratio of fluthiacet-methyl to pyroxhosphone to atrazine can vary widely, but is generally in the range of 1: 33: 284 to 1: 40: 325.

Certain embodiments of the present invention are methods for controlling unwanted plants, comprising applying an insecticidally effective amount of a composition of the present invention to an area where an unwanted plant is required to be controlled.

As used herein, unless otherwise indicated, the term "insecticide" refers to an insecticide that inhibits or kills undesirable plants such as, but not limited to, noxious or annoying weeds, leafy plants, grass, Molecule or combination of molecules, and may be used for crop protection, building protection and grass protection. The term "herbicidal amount" refers to an amount of a herbicide effective to eliminate, destroy, or prevent an observable herbicidal effect on unwanted plant growth, such as unwanted plant necrosis, killing, growth inhibition, reproductive inhibition, proliferation inhibition, And the amount required to exhibit the effect of reducing.

As used herein, the terms "ambient temperature" and "room temperature" refer to any suitable temperature that is generally found in a laboratory or other workplace, and is generally from about 15 ° C to about 30 ° C.

As used herein, "weight percent of ingredients in the composition" includes weight percentages of all liquid and solid ingredients in the composition.

The methods and compositions of the present invention are further exemplified by the following examples. The embodiments are merely illustrative of the invention and should not be construed as limiting, as further modifications of the disclosed invention will be apparent to those skilled in the art. All such modifications are contemplated as falling within the scope of the invention as defined in the claims.

Example 1

Preparation of concentrates for suspension emulsifiers of atrazine, pyroxysulfone and fluthiacet-methyl using fumed alumina as a stabilizer

Step A: Preparation of atrazine / pyroxysulfone suspension concentrate (SC)

A mixture of 179.90 grams of deionized water, 0.10 grams of glacial acetic acid, 36.00 grams of polyethylene glycol, 0.60 grams of defoamer (Dow TM Antifoam AF from Dow Chemical Company), 0.60 grams of preservative [from The Dow Chemical Company 14.10 g of an alkyl EO / PO copolymer nonionic surfactant (Tergitol (registered trademark) XD from The Dow Chemical Company), 20.10 g of an acrylic graft copolymer surfactant [ Terpospus TM G-2500 available from Huntsman Performance Products), 7.80 g of an aqueous dispersion of fumed alumina (Aerodisp < / RTI &gt; W 630 from Ebonic Industries, (L) were added to the beaker and blended for 5 minutes at 4500 rpm with a Silverson homogenizer. The mixture was transferred to an Eiger grinder and milled at 3000 rpm for 15 minutes to achieve a particle size of D90 &lt; 3 mu m.

Step B: Fluticaset-methyl water emulsion (EW)

12.36 g (99.1% purity) of fluthiacet-methyl and 47.50 g of a nonionic polymeric surfactant (Atlox.RTM. 4914 from Crodia CropCare) were dissolved in 475.00 g of aromatic naphthalene depleted solvent Aromatic 200 ND from Mobil Chemicals). The mixture was stirred and heated to about &lt; RTI ID = 0.0 &gt; 65 C &lt; / RTI &gt; This solution was mixed with 0.50 g of glacial acetic acid, 60.00 g of propylene glycol, 50.00 g of polyalkylene oxide block copolymer (Atlas G5000 from Crodia CropCare) in 353.00 g of deionized water, 0.50 g of defoamer [ Dow (TM) Antifoam AF from The Dow Chemical Company] and 1.00 g of preservative (Carton (R) CG / ICP from The Dow Chemical Company). This mixture was homogenized by a Silverton homogenizer until a homogeneous mixture was formed.

Step C: Formation of a suspension emulsifier concentrate (SE)

A suspension emulsifier concentrate was formed by combining 367.82 g of atrazine / piroxysulfone SC from Step A with 51.84 g of fluthiacet-methyl EW from Step B and 4.67 g of deionized water. The resulting composition was stirred until a homogeneous mixture was obtained. The resulting suspension emulsifier concentrate composition was uniformly dispensed into 8 oz glass bottles, sealed, and stored for 2 weeks at an elevated temperature of 54 캜 for stability testing. Analysis by High Performance Liquid Chromatography (HPLC) showed that after two weeks at elevated temperature: Initial analysis - atrazine 42.33%; 5.35% of the Pirox private phone; 0.1% fluthiacet-methyl; Elevated temperature - atrazine 42.48%; 5.4% of the Pirox private phone; 0.1% fluthiacet-methyl; The composition was found to be chemically stable.

Visual inspection of the suspension emulsifier concentrate composition for the second week showed no phase separation or settling, indicating that the composition is physically stable.

Example  2

Manufacture of atrazine / pyroxysulfone suspension concentrate (SC) and fluticaset-methyl emulsion (EW) using fumed alumina as stabilizer

In a similar manner to Example 1, Step A, additional SC compositions were prepared containing atrazine and pyroxysulfone. In a similar manner as in Step B of Example 1, additional EW compositions containing fluthiacet-methyl were prepared. Additional SC compositions are summarized in Table 2A below; Table 2B summarizes additional EW compositions.

[Table 2A]

Figure 112014045532413-pct00001

[Table 2B]

Figure 112014045532413-pct00002

Example  3

Preparation of concentrates for suspension emulsifiers of atrazine, pyroxysulfone and fluthiacet-methyl using fumed alumina as a stabilizer

Step A: Preparation of atrazine / pyroxysulfone suspension concentrate (SC)

(Dow TM Antifoam AF from The Dow Chemical Company), 6.9 grams of preservative (available from Thorpe Specialty Chemicals, Inc.), 2.3 grams of deionized water, 7.7 grams of glacial acetic acid, 463.0 grams of polyethylene glycol, 7.7 grams of defoamer 181.4 g of an alkyl EO / PO copolymer nonionic surfactant (Tergitol (registered trademark) XD from The Dow Chemical Company), 258.5 g of an acrylic graft copolymer A mixture of surfactant [Terpspus (R) G-2500 from Huntsman Performance Products) was added to the slurry tank and mixed until homogeneous. (480.0 g, 99.3% purity) and atrazine (3.862.0 kg, 97.0% purity) were added in portions to the tank such that each addition was thoroughly mixed before the next portion was added. The mixture was transferred to a grinding mill, milled and maintained at a temperature below 30 DEG C until a particle size of D90 < 3 mu m was obtained. The ground mixture was transferred to a blending tank and 138.9 grams of an aqueous dispersion of fumed alumina (Aerodisup (registered trademark) W 630 from Ebornic Industries) was added. The mixture was stirred for 1 hour to obtain 6.79 kg of a suspension concentrate.

Step B: Fluticaset-methyl water emulsion (EW)

141.4 g of fluthiacet-methyl (99.1% purity) and 544.5 g of a non-ionic polymeric surfactant (Atlox.RTM. 4914 from Crodia CropCare) were dissolved in 5.4446 kg of an aromatic naphthalene deterioration solvent Aromatic &lt; / RTI &gt; 200 ND from Sigma) to produce an organic phase. The mixture was stirred by an in-line homogenizer in a 15 L jacketed vessel and heated to about 55 DEG C to form a solution. 5.7 g of glacial acetic acid, 687.7 g of propylene glycol, 573.1 g of polyalkylene oxide block copolymer (Atlas G5000 from Crodia CropCare), 5.70 g of defoamer (Dow from the Dow Chemical Company Trademark) Antifoam AF] and 4.0492 kg of deionized water to a mixing vessel and heated to 55 [deg.] C until a homogeneous mixture was obtained. The warm organic phase was added to the aqueous phase via the recycle line of the in-line homogenizer. Once the addition was complete, the homogenization was continued until a particle size of less than 3 [mu] m was achieved in D90. The mixture was cooled to room temperature and 10.3 grams of preservative (Acticide (TM) MV from Torpreztz Inc.) was added and stirred until a homogeneous mixture of about 11.2 kg was obtained.

Step C: Suspension emulsifier concentrate (SE) formulation

6.658 kg of atrazine / piroxysulfone SC from Step A were combined with 941.0 g of fluthiacet-methyl EW from Step B and 186.0 g of deionized water to form a suspension emulsifier concentrate. The resulting composition was stirred until a homogeneous mixture of 7.77 kg was obtained. These suspension emulsifier preparations were stored in separate sealed glass containers.

Reference Example A

Preparation of a concentrate formulation of a suspension emulsifier of atrazine, pyroxysulfone and fluthiacet-methyl using fumed silica as stabilizer

Step A: Preparation of atrazine / pyroxysulfone suspension concentrate (SC)

0.50 g of polyethylene glycol, 0.50 g of defoamer (Dow TM Antifoam AF from The Dow Chemical Company), 0.75 g of preservative (carton from The Dow Chemical Company) (Trade name: CG / ICP), 11.75 g of an alkyl EO / PO copolymer nonionic surfactant (Tergitol (registered trademark) XD from The Dow Chemical Company), 16.75 g of an acrylic graft copolymer surfactant Terpospus TM G-2500 from Performance Products), 2.50 g of an aqueous dispersion of fumed silica (Aerodisup.RTM. W 7512 S from Econonic Industries, a commonly used emulsion stabilizer) A mixture of 25.75 g of pyroxylsulfone (99.3% purity) and 222.50 g of atrazine (97.0% purity) was added to a 1 L beaker and blended by Silverton homogenizer at 4500 rpm for 5 minutes. The mixture was transferred to an Eiger mill and milled at 3000 rpm for 15 minutes to achieve a particle size of D90 < 3 [mu] m.

Step B: Fluticaset-methyl water emulsion (EW)

18.54 g (99.1% purity) of flutiacet-methyl and 71.25 g of a nonionic polymeric surfactant (Atlox.RTM. 4914 from Crodia CropCare) were dissolved in 712.Og of an aromatic naphthalene deterioration solvent (ExxonMobil Chemical Aromatic &lt; / RTI &gt; 200 ND from &lt; RTI ID = The mixture was stirred and heated to about &lt; RTI ID = 0.0 &gt; 65 C &lt; / RTI &gt; This solution was mixed with 0.75 g of glacial acetic acid, 90.00 g of propylene glycol, 75.00 g of polyalkylene oxide block copolymer (Atlas G5000 from Crodia CropCare) in 527.61 g of deionized water, 0.75 g of defoamer [ Dow (TM) Antifoam AF from Dow Chemical Company] and 2.25 g of preservative (Carton (R) CG / ICP from The Dow Chemical Company). This mixture was homogenized by a Silverton homogenizer until a homogeneous mixture was formed.

Step C: Formation of a suspension emulsifier concentrate (SE)

449.3 g of atrazine / piroxysulfone SC from Step A were combined with 50.8 g of fluthiacet-methyl EW from Step B and 4.67 g of deionized water to form a suspension emulsifier concentrate. The resulting composition was stirred until a homogeneous mixture was obtained. These suspension emulsifier preparations were stored in separate sealed glass containers.

Example 4

Preparation of aqueous suspension concentrates of atrazine, pyroxysulfone and fluthiacet-methyl using fumed alumina as stabilizer

308.72 grams of deionized water, 0.72 grams of glacial acetic acid, 46.88 grams of polyethylene glycol, 0.72 grams of defoamer (Dow TM Antifoam AF from The Dow Chemical Company), 0.72 grams of preservative (available from Thorpe Specialty Chemicals Inc.) 22.96 g of an acrylic graft copolymer surfactant (Terps (registered trademark) G-2500 available from Huntsman Performance Products, Inc.), 20.88 g of a polyalkylene oxide block copolymer [ Atlas G5000 from Crodia Crop Care), 12.32 g of an aqueous dispersion of fumed silica (Aerodisp (registered trademark) W 7512 S from Ebonic Industries, a commonly used emulsion stabilizer), 42.56 (99.3% purity), 342.40 g of atrazine (97.0% purity) and 1.20 g of fluthiacet-methyl (99.1% purity) was added to a 2 L beaker and heated at 4500 rpm Books were blended by a Silverson homogenizer. The mixture was transferred to an Eiger mill and ground until a particle size of D90 < 3 [mu] m was achieved. These SC preparations were stored in separate sealed glass containers.

Example 5

Physical and chemical stability data

A suspension of 1.0 g (1%) or 3.0 g (3%) from Example 3 and Reference Example A added to 99.0 ml or 97.0 ml of water having a hardness of 20 ppm or 500 ppm in a 100 ml Nessler tube A dilute material dispersion study was conducted using an emulsifier concentrate composition. The Nestler tube was sealed with a rubber stopper, and the contents were mixed by inverting the tube 10 times below. The resulting test sample was maintained at ambient temperature. Reproducibility of formulation The formulation was run for 24 hours and the number of reversals required to produce a homogeneous mixture was recorded. Table 4A below summarizes the redistributed data.

[Table 4A]

The resampling data from Example 3 and Reference Example A

Figure 112014045532413-pct00003

The suspension and emulsion concentrate compositions of Example 3 and Example 4 were tested for physical and chemical stability at 24 hours (initial), in a freeze / thaw cycle (at -30 ° C for 2 days / room temperature for 2 Day), and 54 [deg.] C for 2 weeks. The suspension emulsifier of Example 3 was also analyzed for physical and chemical stability at 50 占 폚 for 1 month and 3 months for 1 month at room temperature. The sample viscosity (centipoise (cp)) was measured using a Brookfield RVT viscometer (spindle speed of spindle number 3, 50). The particle size was measured in D90 (90% of the particles reported in micrometer size) using a particle size distribution analyzer (Horiba Particle Scattering Particle Size Distribution Analyzer LA-910). The separation rate (%) was visually determined by measuring the height of the separated layer and dividing the number by the total height of the container. Analysis of active ingredients was performed by HPLC analysis on a weight percent basis. This data is summarized in Table 4B below.

[Table 4B]

Figure 112017074599792-pct00005

As can be seen from the data provided above, the physically and chemically stable compositions can be prepared by mixing the fumed alumina with an agricultural composition such as a suspension emulsifier preparation and a suspension concentrate To the formulation.

While the invention has been described with emphasis on preferred embodiments, it will be apparent to those skilled in the art that changes in the preferred apparatus and method may be employed and that the invention may be practiced otherwise than specifically described herein. Accordingly, the invention also includes all modifications embraced within the spirit and scope of the invention as defined by the following claims.

Claims (7)

i) an aqueous suspension concentrate composition containing pyroxasulfone and atrazine;
ii) an aqueous emulsion composition containing fluthiacet-methyl; And
iii) Fumed alumina
&Lt; / RTI &gt; wherein the composition is a suspoemulsion concentrate composition.
The method according to claim 1,
Wherein the aqueous suspension concentrate further comprises at least one selected from the group consisting of a surfactant component, a pH adjuster, a cryoprotectant, a defoamer, a thickener, and an antimicrobial agent.
The method according to claim 1,
Wherein the aqueous emulsion concentrate further comprises at least one selected from the group consisting of a surfactant component, a pH adjuster, a cryoprotectant, a defoaming agent, a thickener, and an antimicrobial agent.
The method according to claim 1,
Wherein the weight ratio of flutia set-methyl to pyroxhosphone to atrazine is 1: 33: 284 to 1: 40: 325.
i) forming an aqueous suspension concentrate composition comprising a piroxysulfone and atrazine;
ii) forming an aqueous emulsion composition containing fluthiacet-methyl;
iii) blending together the suspension concentrate and the emulsion composition, and
iv) adding fumed alumina and blending the mixture to form a homogeneous mixture
&Lt; / RTI &gt;
i) forming an aqueous suspension concentrate composition comprising a pyroxylsulfone and atrazine, and a fumed alumina;
ii) forming an aqueous emulsion composition containing fluthiacet-methyl;
iii) blending together the suspension concentrate and the emulsion composition to form a homogeneous mixture
&Lt; / RTI &gt;
i) agricultural active ingredients containing fluthiacet-methyl, atrazine and pyroxysulfone;
ii) a surfactant component containing an acrylic graft copolymer and a polyalkylene oxide block copolymer;
iii) defoamer;
iv) biocides;
v) pH adjusting agents;
vi) cryoprotectants; And
vii) Fumed alumina
&Lt; / RTI &gt;
KR1020147013034A 2011-10-18 2012-10-17 Stable formulations containing fumed aluminum oxide KR101931846B1 (en)

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Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3111761B1 (en) 2014-02-28 2024-05-01 Kumiai Chemical Industry Co., Ltd. Agrochemical composition for foliage treatment
CN104094945A (en) * 2014-06-25 2014-10-15 广东中迅农科股份有限公司 Herbicide for corn field
CN106259362A (en) * 2015-06-09 2017-01-04 江苏龙灯化学有限公司 A kind of Synergistic herbicide compositions
KR20200045523A (en) 2017-08-31 2020-05-04 카와사키 주코교 카부시키 카이샤 Gripping device
CN107509733A (en) * 2017-09-12 2017-12-26 河南省农业科学院植物保护研究所 A kind of cornfield weeding composition containing atrazine and sulfone pyrrole grass azoles
CN111200934B (en) * 2017-10-09 2022-12-20 巴斯夫欧洲公司 Novel agrochemical pesticide composition

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2240691C2 (en) 1996-09-23 2004-11-27 Байер Акциенгезелльшафт Herbicide agent based on arylsulfonylaminocarbonyltriazolinones
WO2006027198A1 (en) 2004-09-06 2006-03-16 Basf Aktiengesellschaft (hetero)cyclylcarboxamides for controlling pathogenic fungi
US20100210704A1 (en) 2007-10-18 2010-08-19 Kumiai Chemical Industry Co., Ltd. 3-alkoxy-1-phenylpyrazole derivatives and pesticides
EA201001430A1 (en) 2008-03-11 2011-04-29 Басф Се HERBICIDE COMPOSITIONS CONTAINING PYROXASSULPHONE

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU774112B2 (en) * 2000-03-14 2004-06-17 Sumitomo Chemical Company, Limited Aqueous pesticidal composition
UA78071C2 (en) * 2002-08-07 2007-02-15 Kumiai Chemical Industry Co Herbicidal composition
JP4752182B2 (en) * 2004-03-01 2011-08-17 住友化学株式会社 Insect growth regulator
CN101232885A (en) * 2005-01-25 2008-07-30 神经能质公司 Substituted pyridazinyl- and pyrimidinyl-quinolin-4-ylamine analogues
US20060270559A1 (en) * 2005-05-26 2006-11-30 Nippon Soda Co., Ltd. Method of producing suspended agricultural chemical composition
TW201433263A (en) * 2005-07-04 2014-09-01 Sumitomo Chemical Co Method for producing pesticidal composition and method for controlling weeds
US8110530B2 (en) * 2006-12-21 2012-02-07 Kumiai Chemical Industry Co., Ltd. Herbicidal composition
MX2010011981A (en) * 2008-05-21 2010-12-07 Basf Se Herbicidal composition comprising glyphosate, glufosinate or their salts.

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
RU2240691C2 (en) 1996-09-23 2004-11-27 Байер Акциенгезелльшафт Herbicide agent based on arylsulfonylaminocarbonyltriazolinones
WO2006027198A1 (en) 2004-09-06 2006-03-16 Basf Aktiengesellschaft (hetero)cyclylcarboxamides for controlling pathogenic fungi
US20100210704A1 (en) 2007-10-18 2010-08-19 Kumiai Chemical Industry Co., Ltd. 3-alkoxy-1-phenylpyrazole derivatives and pesticides
EA201001430A1 (en) 2008-03-11 2011-04-29 Басф Се HERBICIDE COMPOSITIONS CONTAINING PYROXASSULPHONE

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WO2013059288A1 (en) 2013-04-25
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CA2852240A1 (en) 2013-04-25

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