GB2615815A - Herbicidal composition comprising fluroxypyr ester and use of the same - Google Patents

Herbicidal composition comprising fluroxypyr ester and use of the same Download PDF

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GB2615815A
GB2615815A GB2202319.6A GB202202319A GB2615815A GB 2615815 A GB2615815 A GB 2615815A GB 202202319 A GB202202319 A GB 202202319A GB 2615815 A GB2615815 A GB 2615815A
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Prior art keywords
ester
fluroxypyr
composition according
general formula
alkenylamide
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GB2615815B (en
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Timothy Bristow James
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Rotam Agrochem International Co Ltd
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Rotam Agrochem International Co Ltd
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    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/34—Nitriles
    • 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
    • A01P13/00—Herbicides; Algicides
    • 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
    • A01P13/00—Herbicides; Algicides
    • A01P13/02—Herbicides; Algicides selective

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

Abstract

Herbicidal emulsifiable concentrate comprising fluroxypyr and alkenylamide solvent Herbicidal composition comprising (1) fluroxypyr or a salt or ester thereof; (2) at least one organic solvent of formula (I), wherein n is from 2 to 20 and (3) at least one emulsifier. The herbicidal ester may be an ester (e.g. fluroxypyr methylheptyl ester) or an alkoxyalkyl ester (e.g. 2-butoxyethyl ester). Preferably, n is 7-9, most preferably the alkenylamide solvent is N,N-dimethyl-9-decenamide. Component (1) may be present in the composition at 100 g/L to 600 g.L-1. The alkenylamide may be present at 200-600 g/L. The emulsifier may be present at 100-200 g.L-1. The composition may comprise a further herbicide, e.g. 2-4D, cyhalofop-butyl. Also claimed is a method for controlling plant growth at a locus, the method comprising applying to the locus a composition described supra. Further claimed is the use of a compound of general formula (I) in which n is from 2 to 20 to stabilise fluroxypyr or a salt or ester thereof in an emulsifiable concentrate.

Description

Intellectual Property Office Application No G1322023196 RTM Date:27 June 2022 The following terms are registered trade marks and should be read as such wherever they occur in this document: Starane Intellectual Property Office is an operating name of the Patent Office www.gov.uk/ipo
HERBICIDAL COMPOSITION COMPRISING FLUROXYPYR ESTER AND USE OF
THE SAME
The present invention relates to a fluroxypyr ester herbicidal composition. The invention further relates to the use of the composition in the control of unwanted plant growth.
Agrochemically active compounds, such as herbicides, pesticides or microbicides, are usually combined with carriers and one or more adjuvants to make a formulated product, which is then provided to end users. On the one hand, the adjuvants and carriers used in such formulations increase the cost of the product and can make the product less suitable for the environment. On the other hand, these ingredients generally make a positive contribution to the properties and effectivenss of the final product. Organic solvents commonly used in formulated agricultural products, in particular hydrocarbon solvents, are examples of carriers with the aforementioned characteristics, that is have a positive effect on the properties of the formulations in which they are employed, but can have an adverse effect on the environment. Due to environmental pressures and policy restrictions, formulators are now seeking to prepare formulated agricultural products that contain little or no petroleum hydrocarbon solvents or chlorinated hydrocarbon solvents, while still achieving the same effects as provided by such solvents in the formulations.
Fluroxypyr (2-[(4-amino-3,5-dichloro-6-fluoro-2-pyridinyl)oxy]acefic acid) is a known highly effective herbicide. Fluroxypyr has the following formula:
CI NH2
OH
CI -2 -
Fluroxypyr is available in the free acid form or, alternatively, as a salt or an ester. Fluroxypyr methylheptyl ester is commercially available as a formulated product sold (RI to) under the name Staranein. (trademark of Dow AgroSciences). It is known to formulate fluroxypyr or salts or esters thereof as an emulsifiable concentrate, for example with a concentration of 200 g acid equivalent/liter, in an aromatic solvent. In view of various economic and environmental factors, there is a need for a formulation having a high concentration of fluroxypyr. For example, it is desirable to provide high-strength formulations to reduce the transportation and storage costs of the product. In addition, there is a need to reduce the amount of packaging materials that must be processed and used to contain the product. Further, there is a need to reduce the amount of organic solvents released into the environment upon use of the formulation. To be usable and effective, high-strength formulations should be stable and maintain their potency after prolonged storage and transportation. Furthermore, the high-strength formulation should be a uniform liquid that is stable at ambient temperature and below. In particular, a high-strength formulation should not produce crystals and precipitates under low temperature or extremely low temperature conditions.
A major limitation of the known aromatic hydrocarbon-based fluroxypyr ester emulsifiable concentrates (EC) is the limited stability thereof at low temperatures when high concentrations of the fluroxypyr active component are employed. Although chlorinated solvents or methylpyrrolidone solvents can be used to prepare a relatively high concentration of an emulsifiable concentrate formulation, these solvents have unfavorable environmental impacts. Furthermore, these solvents do not provide adequate stability of the EC formulation at low temperatures.
Attempts to address this technical problem are known in the art. In order to prepare a low-temperature stable and high-strength fluroxypyr ester emulsifiable concentrate, CN101453892 A discloses the use of an N,N dimethyl octanamide/capramide solvent to prepare a high-strength fluroxypyr methylheptyl ester emulsifiable concentrate. The data presented suggest the EC formulation does not crystallize when stored at -5°C for 2 to 3 weeks, but produces a small amount of crystals while stored at -9.9°C for 3-4 months. It can be concluded therefrom that under extreme environmental conditions of very low temperature, such as -18°C, a higher rate of crystalisation of the active ingredient would occur. This is undesirable for manufacturers, distributors and end users of the product. -j -
There is still a need to solve the problem of storage stability of a high-strength fluroxypyr ester preparation at low temperatures.
It has surprisingly been found that a stable, high-strength fluroxypyr ester emulsifiable concentrate (EC) that exhibits a high level of stability under extremely low temperature conditions can be prepared using as an organic solvent certain alkenylamides. It has been found by testing the formulation in a wide range of fields that the formulation exhbifis an equivalent activity against broad-spectrum broadleaf weeds to the known fluroxypyr formulations based on petroleum hydrocarbon solvents.
In a first aspect, the present invention provides a herbicidal composition comprising: (1) fluroxypyr or a salt or ester thereof; (2) at least one organic solvent of formula (I) wherein n is from 2 to 20; and (3) at least one emulsifier. 15 The composition of the present invention is an emulsifiable concentrate formulation, able to contain fluroxypyr or a salt or ester thereof in high concentrations, while maintaining a high stability, in particular at low temperatures, especially temperatures significantly below 0°C. It has been found that the composition remains stable, without fluroxypyr crystallising out of solution, at sub-zero temperatures, for example temperatures as low as -18°C.
The composition comprises fluroxypyr. The fluroxypyr may be present in the composition in the form of the free acid, as a salt of fluroxypyr, an ester of fluroxypyr or a mixture thereof. Suitable salts of fluroxypyr are alkali metal salts and the ammonium salt. -4 -
Preferably the composition comprises one or more fluroxypyr esters. Suitable esters of fluroxypyr include ester groups of the general formula (II): in which Ri is an alkyl group having from 1 to 12 carbon atoms, more preferably from 2 to 10 carbon atoms; and ester groups of the general formula: -R2 -0 -R3 in which R2 is an alkyl group having from 1 to 6 carbon atoms, more preferably from 2 to 5 carbon atoms and IR3 is an alkyl group having from 1 to 6 carbon atoms, more preferably from 2 to 5 carbon atoms.
R1 in the ester groups of formula (II) may be straight chain or branched. Similarly, in the ester groups of formula (Ill) R2 and/or IR3 may be straight chain or branched.
Preferred ester groups are those of formula (II), especially in which R1 is an alkyl group having from 3 to 9 carbon atoms.
Esters of fluroxypyr may be suitable for the present invention include, for example, 2-butoxy-1-methylethyl ester, 2-butoxyethyl ester, butyl ester, 2-methylpropyl ester, 2-ethylhexyl ester, 1-decyl ester, 1-butoxy-2-propyl ester, methylheptyl ester, and 1-butoxy2-butyl ester. Fluroxypyr methylheptyl ester is a particularly preferred ester for use in the composition of the present invention.
As discussed hereinbefore, an advantage of the composition of the present invention is that it can contain the fluroxypyr compound in a high concentration and the formulation remain stable. The fluroxypyr compound may be present in the composition in an amount of from 100 g/L based on the fluroxypyr acid equivalent, preferably from 150 g/L, more preferably from 180 g/L, still more preferably from 200 g/L, more preferably still from 220 g/L, especially from 250 g/L, more especially from 275 g/L, in particular from 280 g/L, more particularly from 300 g/L. The fluroxypyr compound may be present in the composition in an amount of up to 600 g/L based on the fluroxypyr acid equivalent, preferably up to 550 g/L, more preferably up to 500 g/L, still more preferably up to 450 -5 -g/L, more preferably still up to 400 g/L, especially up to 380 g/L, more especially up to 375 g/L, in particular up to 350 g/L.
In one embodiment, the fluroxypyr compound is an ester of fluroxypyr, preferably fluroxypyr methylheptyl ester, and is present in the composition in an amount of from 300 to 600 g/L, more preferably from 400 to 500 g/L.
The composition further comprises, as a solvent, an alkenylamide of the general formula (I): () in which n is from 2 to 20.
Preferably, the solvent is an alkenylamide of the general formula (I) in which n is 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 15 or 18. More preferably n is from 5 to 12, still more preferably from 6 to 11, more preferably still from 7 to 10, especially 7, 8 or 9. In one preferred embodiment, n is 7.
Most preferably, the organic solvent of formula (I) is N,N-dimethy1-9-decenamide, with a CAS number of 1356964-77-6.
The alkenylamides of the general formula (I) are available commercially. For example, N,N-dimethy1-9-decenamide can be obtained commercially under various trade names, such as Hallcomide 1025 or Steposol® MET-10U (Stepan Company).
The alkenylamide of the general formula (1) is present as a solvent in a sufficient amount to dissolve the required amount of fluroxypyr compound. The alkenylamide of the general formula (I) may be present in an amount of from 50 g/L, preferably from 100 g/L, more preferably from 150 g/L, still more preferably from 200 g/L, more preferably still from 225 g/L, especially from 250 g/L, more especially from 275 g/L, in particular from 300 g/L. The alkenylamide of the general formula (1) may be present in the composition in an amount of up to 850 g/L, preferably up to 800 g/L, more preferably up to 750 g/L, -6 -still more preferably up to 700 g/L, more preferably still up to 650 g/L, especially up to 600 g/L, more especially up to 550 g/L, in particular up to 500 g/L. In one embodiment, the alkenylamide of the general formula (I) is present in the composition in an amount of from 200 to 600 g/L, preferably from 300 to 500 g/L.
The composition of the present invention is an emulsifiable concentrate (EC) formulation, that is a liquid formulation that is readily able for form an emulsion when combined with water. The composition comprises one or more emulsifiers. Suitable emulsifiers for use in formulating an EC composition are known in the art and are commercially available. The emulsifier may be non-ionic, anionic or cationic. Emulsifiers commonly used in EC formulations known in the art are described in "McCutcheon's Detergents and Emulsifiers Annual" (MC Publishing Corp., Ridgewood, New Jersey, 1998) and "Encyclopedia of Surfactants"(Volumes I-III, Chemical publishing Co., New York, 1980-81) Suitable emulsifiers for use in the composition include alkyl sulfates, for example Is diethanolammonium lauryl sulfate; alkyl aryl sulfonates, for example calcium dodecylbenzene sulfonate; alkyl and/or arylalkyl phenol-alkylene oxide addition products, for example nonylphenol-C18 ethoxylate; alcohol-alkylene oxide addition products, for example tridecyl alcohol-C16 ethoxylate; soaps, for example sodium stearate; alkyl naphthalene sulfonates, for example sodium dibutylnaphthalene sulfonate; dialkyl esters of sulfosuccinates, for example sodium bis(2-ethylhexyl) sulfosuccinate; sorbitol esters, for example sorbitan oleate; quaternary amines, for example lauryl trimethyl ammonium chloride; polyethylene glycol esters of fatty acids, for example polyethyldiester stearate; block copolymers of ethylene oxide and propylene oxide; salts of monoalkyl or dialkyl phosphates; and mixtures thereof. The emulsifier may comprise a single emulsifier compound or a combination of two or more emulsifier compounds.
The emulsifier is present in the composition in a sufficient amount to form a stable emulsion upon combination with water. The emulsifier may be present in an amount of from 10 g/L, preferably from 20 g/L, more preferably from 25 g/L, still more preferably from 30 g/L, more preferably still from 35 g/L, especially from 40 g/L, more especially from 45 g/L, in particular from 50 g/L. The emulsifier may be present in the composition in an amount of up to 400 g/L, preferably up to 350 g/L, more preferably up to 300 g/L, still more preferably up to 275 g/L, more preferably still up to 250 g/L, especially up to 225 g/L, more especially up to 200 g/L, in particular up to 500 g/L. In one embodiment, -7 -the emulsifier is present in the composition in an amount of from 10 to 250 g/L, preferably from 50 to 200 g/L, more preferably from 100 to 200 g/L.
The composition may comprise one or more other herbicides, as required to provide the desired range of activity in controlling plant growth. Still further, the composition may comprise one or more other components as known in the art, such as dyes and any other additional ingredients providing functional utility, for example a stabilizer, a fragrance, a viscosity-lowering additive and/or a freezing-point depressant.
The additional herbicidal compounds should not have antagonistic effects on the activity of the fluroxypyr compound used in the present invention. Suitable herbicidal compounds include but are not limited to: 2,4-D, 2,4-MCPA, cyhalofop-butyl, ametryn, aminopyralid, asulam, atrazine, butafenacil, carfentrazone-ethyl, chlorflurenol, chlormequat, chlorpropham, chlorsulfuron, chlortoluron, cinosulfuron, clethodim, clopyralid, cyclosulfamuron, pyroxsulam, dicamba, dichlobenil, dichlorprop-P, diclosulam, diflufenican, diflufenzopyr, diuron, glyphosate, hexazinone, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, MCPA, metsulfuron-methyl, picloram, pyrithiobac-sodium, sethoxydim, sulfometuron, sulfosate, sulfosulfuron, tebuthiuron, terbacil, thiazopyr, thifensulfuron, triasulfuron, tribenuron and triclopyr.
The herbicidal composition of the present invention can be co-formulated with one or more other herbicides, tank mixed with one or more other herbicides, or applied successively with one or more other herbicide compositions.
Dyes can be used in a formulated composition as a marker. Generally speaking, preferred dyes can be any oil soluble dyes selected from the list of inerts exempt from tolerance approved by the EPA. Such dyes include, for example, D&C Red #17, D&C Violet #2 and D&C Green #6. Generally, the concentration of the dyes in the composition is sufficient to provide the required colouration, for example from 0.1 to 1.0 % by weight.
In a further aspect, the present invention provides a method for controlling plant growth at a locus, the method comprising applying to the locus a composition as herein before described. -8 -
In a still further aspect, the present invention provides the use of a composition as hereinbefore described in the control of plant growth at a locus.
In use, the composition of the present invention is combined with water to form an emulsion. The composition readily forms an emulsion when combined with water and techniques for forming the emulsion are known in the art. Typically, the resulting mixture is applied to the target plants or the locus by spraying. Generally, the diluted composition contains from 0.0001 to 5.0 % by weight of the fluroxypyr compound. The composition may be applied to a range of crops to control unwanted plant growth, for example cereals, ranges and pastures.
In a further aspect, the present invention provides a herbicidal emulsion formulation comprising a composition as hereinbefore described in combination with water.
As described above, the composition of the present invention is stable for prolonged periods of time under a range of conditions. In particular, the composition is stable at low temperatures, more particularly temperatures below zero, such as temperatures down to -18°C and below, with the fluroxypyr compound remaining in solution and not crystalising out of the formulation.
In a further aspect, the present invention provides the use of an alkenylamide of the general formula (I): in which n is from 2 to 20, to stabilise fluroxypyr or a salt or ester thereof in an emulsifiable concentrate (EC) formulation.
Embodiments of the present invention will now be described, for illustration purposes only, by way of the following working examples. -9 -
Unless otherwise indicated, percentages are percent by weight.
EXAMPLES
Example 1 -Fluroxypyr methylheptyl ester 600 q/L EC An emulsifiable concentrate (EC) formulation was prepared by combining and mixing the following components to form a uniform liquid composition: Fluroxypyr methylheptyl ester 600 g/L N, N-dimethy1-9-decenamide (Steposole MET-10U, Stepan) 400 g/L Calcium dodecylbenzene sulfonate 80 g/L Example 2 -Fluroxypyr methylheptyl ester 480 g/L EC An emulsifiable concentrate (EC) formulation was prepared by combining and mixing the following components to form a uniform liquid composition: Fluroxypyr methylheptyl ester 480 g/L N, N-dimethy1-9-decenamide (Hallcomide 1025, Stepan) 404 g/L Polyethylene tristyrylphenol phosphate 13 g/L Tensiofix N9811HF (OmniChem, NV) 78.5 g/L Ethoxylated tristyrylphenol 78.6 g/L -10 -Example 3 -Fluroxypyr butyl ester 300 g/L EC An emulsifiable concentrate (EC) formulation was prepared by combining and mixing the following components to form a uniform liquid composition: Fluroxypyr butyl ester 300 g/L N,N-dimethy-11-dodecenylamide 600 g/L Castor oil ethoxylate 100 g/L Calcium dodecylbenzene sulfonate 80 g/L Example 4 -Fluroxypyr ethylhexyl ester 500 q/L EC An emulsifiable concentrate (EC) formulation was prepared by combining and mixing the following components to form a uniform liquid composition: Fluroxypyr ethylhexyl ester 500 g/L N,N-dimethy1-7-octenylamide 300 g/L Methyl oleate 200 g/L Sorbitan oleate 50 g/L EO-PO block copolymer 30 g/L Example 5 -Fluroxypyr methylheptyl ester + cyhalofop-butyl (350 + 150) g/L EC An emulsifiable concentrate (EC) formulation was prepared by combining and mixing the following components to form a uniform liquid composition: Fluroxypyr methylheptyl ester 350 g/L Cyhalofop-butyl 150 g/L N,N-dimethy1-8-nonenylamide 400 g/L Polyethyldiester stearate 50 g/L Diethanolammonium lauryl sulfate 100 g/L Polyethylene tristyrylphenol phosphate 30 g/L Comparative Example 1 -Fluroxypyr methylheptyl ester 600 q/L EC An emulsifiable concentrate (EC) formulation was prepared by combining and mixing the following components to form a uniform liquid composition: Fluroxypyr methylheptyl ester 600 g/L Aromatic hydrocarbon solvent 400 g/L Calcium dodecylbenzene sulfonate 80 g/L -12 -Comparative Example 2 -Fluroxypyr methylheptyl ester 480 g/L EC An emulsifiable concentrate (EC) formulation was prepared by combining and mixing the following components to form a uniform liquid composition: Fluroxypyr methylheptyl ester 480 g/L N-octyl pyrrolidone 404 g/L Polyethylene tristyrylphenol phosphate 13 g/L Tensiofix N9811HF (OmniChem, nv) 78.5 g/L Ethoxylated tristyrylphenol 78.6 g/L Comparative Example 3 -Fluroxypyr butyl ester 300 g/L EC An emulsifiable concentrate (EC) formulation was prepared by combining and mixing the following components to form a uniform liquid composition: Fluroxypyr butyl ester 300 g/L Cyclohexanone 600 g/L Castor oil ethoxylate 100 g/L Calcium dodecylbenzene sulfonate 80 g/L -13 -Comparative Example 4 -Fluroxypyr ethylhexyl ester 500 g/L EC An emulsifiable concentrate (EC) formulation was prepared by combining and mixing the following components to form a uniform liquid composition: Fluroxypyr ethylhexyl ester 500 g/L Methyl oleate 500 g/L Sorbitan oleate 50 g/L EO-PO block copolymer 30 g/L Comparative Example 5 -Fluroxypyr methylheptyl ester + cyhalofop-butyl (350 + 150) g/L EC An emulsifiable concentrate (EC) formulation was prepared by combining and mixing the following components to form a uniform liquid composition: Fluroxypyr methylheptyl ester 350 g/L Cyhalofop-butyl 150 g/L Aromatic hydrocarbon solvent 400 g/L Polyethyldiester stearate 50 g/L Diethanolammonium lauryl sulfate 100 g/L -14 -Polyethylene tristyrylphenol phosphate 30 g/L Comparative Example 6-CN101453892 A Example 1 Example 1 of CN101453892 A was repeated to prepare a fluroxypyr methylheptyl ester 480 g/L EC formulation. An emulsifiable concentrate (EC) formulation was prepared by combining and mixing the following components to form a uniform liquid composition: Fluroxypyr methylheptyl ester 480 g/L Mixture of N,N-dimethyl octanamide/capramide 404 g/L Polyethylene tristyrylphenol phosphate 13 g/L Tensiofix N9811HF (OmniChem, nv) 78.5 g/L Ethoxylated tristyrylphenol 78.6 g/L Low-temperature Stability The compostions of Examples 1 to 5 and Comparative Example 1 to 6 were tested for their low temperature storage stability.
Samples of each composition were placed in storage at 0°C, -5°C, -10°C and -18°C. The stability of each of the samples was observed after 1 month and 2 months.
The results of the observatons are shown in Table 1 below.
Table 1
Sample 0°C -5°C -10°C -18°C 1 month 2 months 1 month 2 months 1 month 2 months 1 month 2 months Example 1 No No No No No No No No crystallization crystallization crystallization crystallization crystallization crystallization crystallization crystallization Example 2 No No No No No No No No crystallization crystallization crystallization crystallization crystallization crystallization crystallization crystallization Example 3 No No No No No No No No crystallization crystallization crystallization crystallization crystallization crystallization crystallization crystallization Example 4 No No No No No No No No crystallization crystallization crystallization crystallization crystallization crystallization crystallization crystallization Example 5 No No No No No No No No crystallization crystallization crystallization crystallization crystallization crystallization crystallization crystallization -16 -Comparative No No A very small A small More crystals More crystals More crystals More crystals Example 1 crystallization crystallization amount of amount of crystals crystals Comparative No No A very small A small More crystals More crystals More crystals More crystals Example 2 crystallization crystallization amount of amount of crystals crystals Comparative No No A very small A small More crystals More crystals More crystals More crystals Example 3 crystallization crystallization amount of amount of crystals crystals Comparative No No A very small A small More crystals More crystals More crystals More crystals Example 4 crystallization crystallization amount of amount of crystals crystals Comparative No No A very small A small More crystals More crystals More crystals More crystals Example 5 crystallization crystallization amount of amount of crystals crystals -17 -A very small A small Comparative No No No No Example 6 crystallization crystallization crystallization crystallization amount of amount of More crystals More crystals crystals crystals From a review of the results presented in Table 1 above, it can be seen that the emulsifiable concentrate (EC) composition of the present invention, employing an alkenylamide of the general formula (I) exhibited a very high stability during long term storage at very low temperatures. In particular, the composition remained clear and uniform, with no crystallisation of the active fluroxypyr compound being observable. In contrast, the comparative EC compositions employing solvents known in the art exhibited very poor stability, especially after storage at temperatures of -10°C and below.

Claims (19)

  1. -19 -CLAIMS A herbicidal composition comprising: (1) fluroxypyr or a salt or ester thereof; (2) at least one organic solvent of formula (I): wherein n is from 2 to 20; and (3) at least one emulsifier.
  2. 2. The herbicidal composition according to claim 1, wherein fluroxypyr is present in the composition in the form of the free acid, as a salt of fluroxypyr, an ester of fluroxypyr or a mixture thereof.
  3. 3. The herbicidal composition according to claim 2, wherein fluroxypyr is present in the composition as an ester comprising an ester group of the general formula (II): R1 (II) in which Ri is an alkyl group having from 1 to 12 carbon atoms, more preferably from 2 to 10 carbon atoms; or an ester group of the general formula (Ill): -R2 -0 R3 (Ill) -20 -in which R2 is an alkyl group having from 1 to 6 carbon atoms, more preferably from 2 to 5 carbon atoms and R3 is an alkyl group having from 1 to 6 carbon atoms, more preferably from 2 to 5 carbon atoms.
  4. 4. The herbicidal composition according to claim 3, wherein the ester of fluroxypyr is selected from 2-butoxy-1-methylethyl ester, 2-butoxyethyl ester, butyl ester, 2-methylpropyl ester, 2-ethylhexyl ester, 1-decyl ester, 1-butoxy-2-propyl ester, methylheptyl ester, and 1-butoxy-2-butyl ester, preferably fluroxypyr methylheptyl ester.
  5. 5. The herbicidal composition according to any preceding claim, wherein fluroxypyr compound is present in the composition in an amount of from 100 g/L to 600 g/L based on the fluroxypyr acid equivalent.
  6. 6. The herbicidal composition according to any preceding claim, wherein the solvent is an alkenylamide of the general formula (I) in which n is 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 15 or 18.
  7. 7. The herbicidal composition according to claim 6, wherein the solvent is an alkenylamide of the general formula (I) in which n is from 5 to 12, preferably from 6 to 11, more preferably from 7 to 10, especially 7, 8 or 9
  8. 8. The herbicidal composition according to claim 6, wherein the solvent is an alkenylamide of the general formula (I) in which n is 7, preferably N,N-dimethy1-9-decenamide. -21 -
  9. 9. The herbicidal composition according to any preceding claim, wherein the alkenylamide of the general formula (I) is present in the composition in an amount of from 200 to 600 g/L, preferably from 300 to 500 g/L.
  10. 10. The herbicidal composition according to any preceding claim, wherein the emulsifier is selected from alkyl sulfates, for example diethanolammonium lauryl sulfate; alkyl aryl sulfonates, for example calcium dodecylbenzene sulfonate; alkyl and/or arylalkyl phenol-alkylene oxide addition products, for example nonylphenol-C18 ethoxylate; alcohol-alkylene oxide addition products, for example tridecyl alcohol-Cis ethoxylate; soaps, for example sodium stearate; alkyl naphthalene sulfonates, for example sodium dibutylnaphthalene sulfonate; dialkyl esters of sulfosuccinates, for example sodium bis(2-ethylhexyl) sulfosuccinate; sorbitol esters, for example sorbitan oleate; quaternary amines, for example lauryl trimethyl ammonium chloride; polyethylene glycol esters of fatty acids, for example polyethyldiester stearate; block copolymers of ethylene oxide and propylene oxide; salts of monoalkyl or dialkyl phosphates; and mixtures thereof.
  11. 11. The herbicidal composition according to any preceding claim, wherein the emulsifier is present in the composition in an amount of from 10 to 250 g/L, preferably from 50 to 200 g/L, more preferably from 100 to 200 g/L.
  12. 12. The herbicidal composition according to any preceding claim, further comprising a herbicide selected from 2,4-D, 2,4-MCPA, cyhalofop-butyl, ametryn, aminopyralid, asulam, atrazine, butafenacil, carfentrazone-ethyl, chlorflurenol, chlormequat, chlorpropham, chlorsulfuron, chlortoluron, cinosulfuron, clethodim, clopyralid, cyclosulfamuron, pyroxsulam, dicamba, dichlobenil, dichlorprop-P, diclosulam, diflufenican, diflufenzopyr, diuron, glyphosate, hexazinone, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, MCPA, metsulfuron-methyl, picloram, pyrithiobac-sodium, sethoxydim, sulfometuron, sulfosate, sulfosulfuron, tebuthiuron, terbacil, thiazopyr, thifensulfuron, triasulfuron, tribenuron and triclopyr.-22 -
  13. 13. A herbicidal emulsion formulation comprising a composition according to any preceding claim in combination with water.
  14. 14. A method for controlling plant growth at a locus, the method comprising applying to the locus a composition according to any of claims 1 to 12 or a formulation according to claim 13.
  15. 15. Use of a composition according to any of claims 1 to 12 or a formulation according to claim 13in the control of plant growth at a locus.
  16. 16. Use of an alkenylamide of the general formula (I): in which n is from 2 to 20, to stabilise fluroxypyr or a salt or ester thereof in an emulsifiable concentrate (EC) formulation.
  17. 17. The use according to claim 16, wherein the alkenylamide is of the general formula (I) in which n is 3,4, 5, 6, 7, 8, 9, 10, 11, 12. 15 or 18.
  18. 18. The use according to claim 17, wherein the alkenylamide is of the general formula (I) in which n is from 5 to 12, preferably from 6 to 11, more preferably from 7 to 10, especially 7, 8 or 9.-23 -
  19. 19. The use according to claim 18, wherein the alkenylamide is of the general formula (1) in which n is 7, preferably N,N-dimethy1-9-decenamide.
GB2202319.6A 2022-02-21 2022-02-21 Herbicidal composition comprising fluroxypyr ester and use of the same Active GB2615815B (en)

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US20130210627A1 (en) * 2009-12-29 2013-08-15 Syngenta Crop Protection Llc Pesticidal composition
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CN112471144A (en) * 2020-12-28 2021-03-12 安徽兴隆化工有限公司 Processing technology of clodinafop-propargyl microemulsion
CN112715570A (en) * 2019-10-28 2021-04-30 海利尔药业集团股份有限公司 Herbicidal composition containing metolachlor and fluroxypyr
CN113880116A (en) * 2021-10-27 2022-01-04 利尔化学股份有限公司 Method for separating and refining fluorine-containing sodium chloride salt

Patent Citations (8)

* Cited by examiner, † Cited by third party
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US20080004182A1 (en) * 2006-06-29 2008-01-03 Dow Agrosciences Llc High-strength, low-temperature stable herbicidal formulations of fluroxypyr esters
US20090215797A1 (en) * 2008-02-26 2009-08-27 Dow Agrosciences Llc Stable emulsifiable concentrate formulation
US20130210627A1 (en) * 2009-12-29 2013-08-15 Syngenta Crop Protection Llc Pesticidal composition
US20180153160A1 (en) * 2015-05-07 2018-06-07 Nufarm Australia Limited Emulsifiable concentrate comprising picolinic acid herbicide
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