WO2024077353A1 - Composition herbicide - Google Patents

Composition herbicide Download PDF

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Publication number
WO2024077353A1
WO2024077353A1 PCT/AU2023/051009 AU2023051009W WO2024077353A1 WO 2024077353 A1 WO2024077353 A1 WO 2024077353A1 AU 2023051009 W AU2023051009 W AU 2023051009W WO 2024077353 A1 WO2024077353 A1 WO 2024077353A1
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WO
WIPO (PCT)
Prior art keywords
herbicide composition
herbicide
composition
salt
nonanoate
Prior art date
Application number
PCT/AU2023/051009
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English (en)
Inventor
Peter Vaughan
Original Assignee
Nontox Pty Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from AU2022902988A external-priority patent/AU2022902988A0/en
Application filed by Nontox Pty Ltd filed Critical Nontox Pty Ltd
Publication of WO2024077353A1 publication Critical patent/WO2024077353A1/fr

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Classifications

    • 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
    • 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
    • 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
    • A01N37/02—Saturated carboxylic acids or thio analogues thereof; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P3/00—Fungicides

Definitions

  • the present disclosure generally relates to herbicide compositions comprising nonanoic acid or any ester of salt thereof, which can be used to control unwanted vegetation, fungi or algae.
  • the present disclosure also relates to processes for preparing the herbicide compositions.
  • the present disclosure also relates to methods of controlling unwanted vegetation, fungi or algae using the herbicide compositions.
  • the present disclosure also relates to kits comprising the herbicide compositions.
  • Nonanoic acid is a naturally-occurring water insoluble, saturated fatty acid with nine carbon atoms.
  • Nonanoic acid is an effective non-selective herbicide and works by stripping the waxy cuticle of the plant, causing cell disruption, cell leakage, and death by desiccation.
  • nonanoic acid based herbicide formulations which are typically provided as emulsifiable concentrates having a high concentration of nonanoic acid (e.g. 525 g/L nonanoic acid). These concentrates are diluted with water prior to spray application to weed.
  • nonanoic acid e.g. 525 g/L nonanoic acid
  • these concentrates are diluted with water prior to spray application to weed.
  • one of the major problems with these emulsifiable concentrates is that they are highly acidic, corrosive to equipment, and is a skin and eye irritant in both concentrate and diluted forms, making it difficult to handle.
  • the present disclosure is based, in part, on the finding that herbicide compositions comprising a nonanoate salt as the herbicide (e.g. a conjugate salt of nonanoic acid) and polar solvents display good non-selective activity against a broad spectrum of plants yet is comparatively less-toxic and easier to handle compared to other commercial formulations.
  • a nonanoate salt e.g. a conjugate salt of nonanoic acid
  • polar solvents display good non-selective activity against a broad spectrum of plants yet is comparatively less-toxic and easier to handle compared to other commercial formulations.
  • certain polar solvents not only improve the solubility of the nonanoate salt and as a result can provide herbicide compositions having high nonanoate salt loadings (e.g. 200 g/L or more), and surprisingly the herbicide compositions remain pourable and of a desirable lower viscosity, making it easy to handle and use as a herbicide.
  • the present disclosure provides a herbicide composition comprising a nonanoate salt and a polar solvent.
  • the herbicide composition may also comprise an aqueous liquid carrier.
  • the herbicide composition may be of lower viscosity, for example may have a dynamic viscosity of less than about 500 mPa.s when measured using a rotational viscometer at 20 rpm and at a temperature of 20°C.
  • a herbicide composition comprising: a) a nonanoate salt; b) a polar solvent; and c) an aqueous liquid carrier, wherein the herbicide composition has a dynamic viscosity of less than about 500 mPa.s when measured using a rotational viscometer at 20 rpm and at a temperature of 20°C.
  • a herbicide composition consisting of a) a nonanoate salt; b) a polar solvent; c) an aqueous liquid carrier; and d) optionally one or more herbicidally or agriculturally acceptable additives/excipients, wherein the herbicide composition has a dynamic viscosity of less than about 500 mPa.s when measured using a rotational viscometer at 20 rpm and at a temperature of 20°C.
  • a herbicide formulation comprising a diluted herbicide composition as defined above.
  • a process of preparing a herbicide composition as defined above comprising mixing together nonanoic acid, a polar solvent, an alkali reactant, and an aqueous liquid carrier and optionally one or more herbicidally or agriculturally acceptable additives/excipients under conditions effective to form the herbicide composition, wherein the nonanoic acid reacts with the alkali reactant upon mixing the to form a nonanoate salt.
  • a herbicidally effective amount of the herbicide composition defined above or the herbicide formulation defined above comprising applying a herbicidally effective amount of the herbicide composition defined above or the herbicide formulation defined above to an area affected or likely to be affected by the unwanted vegetation, fungi or algae.
  • kits comprising: a) the herbicide compositions as defined above or the herbicide formulation as defined above; and b) a spray applicator.
  • a) the herbicide compositions as defined above or the herbicide formulation as defined above may also apply to the processes, methods, and/or kits described herein. Any embodiment herein shall be taken to apply mutatis mutandis to any other embodiment unless specifically stated. It will also be appreciated that other aspects, embodiments and examples of the herbicide composition or formulation, processes, methods, and/or kits are described herein.
  • certain features that are, for clarity, described herein in the context of separate embodiments may also be provided in combination in a single embodiment.
  • various features that are, for brevity, described in the context of a single embodiment may also be provided separately or in any sub-combination.
  • composition and “formulation” as used herein are intended to encompass a product comprising the specified ingredients in the specified amounts, as well as any product which results, directly or indirectly, from combination of the specified ingredients in the specified amounts.
  • control or “control”, “modifying” or “modification” and variations thereof, refer to intervention designed to alter the natural course of plant growth including plant death, desecration, retardation, dwarfing, leaf burn, undermining of plant structure or cellular destruction.
  • substantially free generally refers to the absence of that compound or component in the herbicide composition, other than any trace amounts or impurities that may be present, for example this may be an amount by weight % in the total herbicide composition of less than about 1%, 0.1%, 0.01%, 0.001%, or 0.0001%.
  • a "herbicidally effective amount” means the quantity of one or more components in the disclosed herbicide compositions that is capable of producing a controlling or modifying effect on the growth of plants.
  • plant refers to all physical parts of a plant including seeds, seedlings, saplings, roots, tubers, stems, stalks, foliage and fruits.
  • the present disclosure generally relates to herbicide compositions comprising a nonanoate salt and polar solvent.
  • the herbicide composition comprises a nonanoate salt.
  • Nonanoic acid also called pelargonic acid
  • Nonanoic acid is a naturally-occurring water insoluble, saturated fatty acid with nine carbon atoms.
  • Nonanoic acid is an effective non-selective herbicide and works by stripping the waxy cuticle of the plant, causing cell disruption, cell leakage, and death by desiccation.
  • Nonanoic acid has the following structure:
  • Salts of nonanoic acid also function effectively as a non-selective herbicide, and is also substantially water soluble, non-toxic and biodegradable.
  • Salts of nonanoic acid are called nonanoate salts and can be prepared by mixing a suitable base/alkali reactant (e.g. ammonium hydroxide, potassium hydroxide, sodium hydroxide and the like) with nonanoic acid to form the conjugate salt.
  • a suitable base/alkali reactant e.g. ammonium hydroxide, potassium hydroxide, sodium hydroxide and the like
  • ammonium hydroxide (NH4OH) and nonanoic acid can be mixed under suitable conditions to form ammonium nonanoate, which is an effective water soluble broad-spectrum contact herbicide.
  • Ammonium nonanoate has the following structure:
  • nonanoate salts other than ammonium nonanoate can be easily prepared by selecting a suitable alkali reactant as described herein.
  • the concentration of nonanoate salt in the herbicide composition can vary, provided the composition remains of a suitable lower viscosity and is pourable.
  • the concentration of nonanoate salt in the herbicide composition (in g/L) is at least about 200, 225, 250, 275, 300, 325, 350, 375, 400, 425, 450, 475, 500, 525, 550, 575 or 600.
  • the concentration of nonanoate salt in the herbicide composition (in g/L) is less than about 600, 575, 550, 525, 500, 475, 450, 425, 400, 375, 350, 325, 300 or 200.
  • the concentration of nonanoate salt may be in a range provided by any two of these upper and/or lower values, for example the concentration of nonanoate salt in the herbicide composition (in g/L) may be between about 200 to about 600, between about 300 to about 600, or between about 350 to about 500. In one embodiment, the concentration of nonanoate salt in the herbicide composition (in g/L) may be about 440. [0039] The concentration of nonanoate salt in the herbicide composition may also be provided as the nonanoic acid equivalent concentration. For example, a herbicide composition containing about 440 g/L of ammonium nonanoate has a nonanoic acid equivalent concentration of about 400 g/L of nonanoic acid. The person skilled in the art can readily ascertain the nonanoic acid equivalent concentration.
  • the nonanoic equivalent concentration in the herbicide composition (in g/L) is at least about 150, 175, 200, 225, 250, 275, 300, 325, 350, 375, 400, 425, 450, 450, 475, 500, 525, or 550. In one embodiment, the nonanoic equivalent concentration in the herbicide composition (in g/L) is less than about 550, 525, 500, 475, 450, 425, 400, 375, 350, 325, 300, 275, 250, 175 or 150.
  • the nonanoic equivalent concentration in the herbicide composition may be in a range provided by any two of these upper and/or lower values, for example the nonanoic equivalent concentration in the herbicide composition (in g/L) may be between about 250 to about 550, or between about 350 to about 450. In one embodiment, the concentration of nonanoate salt in the herbicide composition (in g/L) may be about 400.
  • the concentration of nonanoate salt in the herbicide composition may also be provided as a % w/w of the total weight of the composition.
  • a herbicide composition containing about 440 g/L ammonium nonanoate has a nonanoate salt concentration of about 44% w/w of the total weight of the composition.
  • the nonanoic acid equivalent concentration is about 40% w/w of the total weight of the composition.
  • the concentration of nonanoate salt in the herbicide composition is at least about 20, 22.5, 25, 27.5, 30, 32.5, 35, 37.5, 40, 42.5, 45, 47.5, 50, 52.5, 55, 57.5 or 60. In one embodiment, the concentration of nonanoate salt in the herbicide composition (in % w/w of the total composition) is less than about 60, 57.5, 55, 52.5, 50, 47.5, 45, 42.5, 40, 37.5, 35, 32.5, 30, 27.5, 25, 22.5 or 20.
  • the concentration of nonanoate salt may be in a range provided by any two of these upper and/or lower values, for example the concentration of nonanoate salt in the herbicide composition (in % w/w of the total composition) may be between about 30 to about 60, or between about 35 to about 50. In one embodiment, the concentration of nonanoate salt in the herbicide composition (in % w/w of the total composition) may be about 44.
  • the nonanoic equivalent concentration in the herbicide composition (in % w/w of the total composition) is at least about 15, 17.5, 20, 22.5, 25, 27.5, 30, 32.5, 35, 37.5, 40, 42.5, 45, 47.5, 50, 52.5, or 55. In one embodiment, the nonanoic equivalent concentration in the herbicide composition (in % w/w of the total composition) is less than about 50, 47.5, 45, 42.5, 40, 37.5, 35, 32.5, 30, 27.5, 25, 22.5, 201, 17.5 or 15.
  • the nonanoic equivalent concentration in the herbicide composition may be in a range provided by any two of these upper and/or lower values, for example the nonanoic equivalent concentration in the herbicide composition (in % w/w of the total composition) may be between about 25 to about 55, or between about 35 to about 45. In one embodiment, the nonanoic equivalent concentration in the herbicide composition (in % w/w of the total composition) may be about 400.
  • the nonanoate salt may be any herbicidally effective salt of nonanoic acid.
  • the nonanoate salt may be selected from the group consisting of an ammonium salt, a sodium salt, a potassium salt a calcium salt, a cadmium salt or a zinc salt of nonanoic acid.
  • the nonanoate salt is ammonium nonanoate.
  • Ammonium nonanoate can be prepared by mixing nonanoic acid with ammonium hydroxide (e.g. a source of ammonium cation). Ammonium nonanoate is the conjugate salt of nonanoic acid.
  • the herbicide compositions described herein may have a less acidic pH (i.e. more alkaline pH) compared to nonanoic acid containing herbicide formulations/concentrates, which are highly acidic, corrosive to equipment, a skin irritant and serious eye irritant both as the concentrate and also in its diluted form.
  • the herbicide composition has a pH of between about 5 to about 10.
  • the herbicide composition has a pH of at least about 5, 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 9.5 or 10.
  • the pH of the herbicide composition may be a range provided by any two of these values, for example the herbicide composition may have a pH of between about 7 to about 9.
  • the pH of the herbicide composition may be between about 7.5 to about 8.5.
  • the herbicide composition comprises a polar solvent.
  • solvent has its general meaning understood in the art, for instance a material that dissolves another substance.
  • the solvent is typically a liquid.
  • polar solvent refers to a solvent that contains a partial positive and partial negative charge (i.e. has a dipole moment).
  • a solvents polarity can readily be determined by its dielectric constant, which measured the solvent’ s tendency to partly cancel the field strength of the electric field of a charge particle immersed in it.
  • the higher the dielectric constant the more polar the solvent is.
  • the dielectric constant can be measured using various testing protocols, including according to ASTM D924.
  • the polar solvent has a dielectric constant of at least 5, preferably at least 10, more preferably at least 15, and even more preferably at least 20, for example between about 5 to about 80, between about 10 to about 80, between about 15 to about 80, or between about 20 to about 80.
  • Any suitable polar solvent can be used provided it can solubilise to some degree the nonanoate salt in the aqueous liquid carrier.
  • the polar solvent is a hydrotrope.
  • a “hydrotrope” is a solvent that solubilises compounds in aqueous solutions by means other than micellar solubilisation.
  • hydrotropes comprise a hydrophilic part and a hydrophobic part (similar to surfactants), but the hydrophobic part is generally too small to cause spontaneous self-aggregation. Additionally, hydrotropes do not have a critical concentration above which self-aggregation spontaneously starts to occur.
  • the nonanoate salt is also referred to as a soap salt and has limited solubility in water, especially at high concentrations which can result in highly viscous composition having a paste like consistency. Such thick compositions are not readily pourable.
  • the present inventors have surprisingly identified that the use of certain polar solvents, including for example hydrotropes, not only improves the solubility of the nonanoate salt in the aqueous liquid carrier and as a result can provide herbicide compositions having high nonanoate salt loadings (e.g. 200 g/L or more), but despite this high nonanoate salt concentration, the herbicide compositions surprisingly remain pourable and of a desirable lower viscosity, making it easy to handle and use as a herbicide.
  • high nonanoate salt loadings e.g. 200 g/L or more
  • hydrotrope Any suitable hydrotrope can be used.
  • the hydrotrope may comprise amide functional groups, ester functional groups, ether functional groups, or alcohol functional groups, or a combination thereof.
  • the hydrotrope is an amide (including a lactamide or a cyclic amide such as a lactam), an alcohol, an esteramide, or a glycol, or a mixture thereof. In one embodiment, the hydrotrope is an esteramide.
  • esteramide refers to a solvent which comprises both at least one amide functional group and at least one ester functional group.
  • the esteramide is methyl 5-(dimethylamino)-2-methyl-5-oxopentanoate (which can be supplied as Rhodiasolv® PolarClean). This esteramide can also act as a crystal growth inhibitor and thus may improve the cold stability of the herbicide composition.
  • the hydrotrope is an amide.
  • the amide solvent is a lactamide.
  • the lactamide is 2-hydroxy-N,N- dimethylpropanamide (which can be supplied as Agnique® AMD 3L).
  • the amide solvent is a lactam (i.e. a cyclic amide).
  • the lactam is N-butyl-2-pyrrolidone (Genagen® NBP).
  • the hydrotrope is a glycol.
  • the glycol solvent is diethylene glycol.
  • the polar solvent is a bio-based solvent.
  • bio-based means that the solvent is derived in-part or in-full from a biological source as opposed to being synthetically derived. While not precluded from being used as a polar solvent in the present herbicide compositions, some synthetic polar solvents may be regarded as being more difficult to handle due to toxicity concerns. Therefore according to some embodiments or examples, using a bio-based polar solvent may provide additional advantages such as the provision of an easier to handle herbicide composition.
  • Agnique® AMD 3L can be regarded as a safe, polar solvent which is partially bio-based, being derived from lactic acid obtained from fermentation.
  • Rhodiasolv® PolarClean is also naturally derived as opposed to synthetic solvents.
  • the polar solvent is a polar aprotic solvent.
  • the polar aprotic solvent may be an esteramide as described herein, such as Rhodiasolv® PolarClean. Other polar aprotic solvents are also contemplated.
  • the polar solvent is a polar protic solvent.
  • the polar protic solvent is a lactamide as described herein, such as Agnique® AMD 3L. Other polar protic solvents are also contemplated.
  • the concentration of polar solvent in the herbicide composition may be in an amount effective to solubilise the nonanoate salt.
  • the concentration of the polar solvent in the herbicide composition (in g/L) is between about 50 to about 200. In one embodiment, the concentration of the polar solvent in the herbicide composition (in g/L) is at least about 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80, 85, 90, 95, 100, 105, 110, 115, 120, 130, 140, 150, 200, 250, 300, 350, 400, 450 or 500.
  • the concentration of the polar solvent in the herbicide composition is less than about 500, 450, 400, 350, 300, 250, 200, 150, 140, 130, 120, 115, 110, 105, 100, 95, 90, 85, 80, 75, 70, 65, 60, 55, 50, 45, 40, 35, 30, 25, 20, 15 or 10.
  • the concentration of the polar solvent may be in a range provided by any two of these upper and/or lower values, for example the concentration of the polar solvent in the herbicide composition (in g/L) may be between about 75 to about 150.
  • the concentration of polar solvent in the herbicide composition may also be provided as a % w/w of the total weight of the composition.
  • the concentration of polar solvent in the herbicide composition (in % w/w of the total weight of the composition) is between about 5 to about 20.
  • the concentration of polar solvent in the herbicide composition (in % w/w of the total weight of the composition) is at least about 1, 1.5, 2, 2.5, 3, 3.5, 4, 4.5, 5, 5.5, 6, 6.5, 7, 7.5, 8, 8.5, 9, 9.5, 10, 10.5, 11, 11.5, 12, 13, 14, 15, 20, 25, 30, 35, 40, 45 or 50.
  • the concentration of the polar solvent in the herbicide composition (in g/L) is less than about 50, 45, 40, 35, 30, 25, 20, 15, 14, 13, 12, 11.5, 11, 10.5, 10, 9.5, 9, 8.5, 8, 7.5, 7, 6.5, 6, 5.5, 5, 4.5, 4, 3.5, 3, 2.5, 2, 1.5 or 1.
  • the concentration of the polar solvent may be in a range provided by any two of these upper and/or lower values, for example the concentration of the polar solvent in the herbicide composition (in % w/w of the total composition) may be between about 7.5 to about 15.
  • the polar solvent comprises less than about 30% w/v of a dicarboxylic acid ester (e.g. a dibasic ester). In one embodiment, the polar solvent does not comprise dimethyl azelate.
  • Aqueous liquid carrier and other excipients are included in Aqueous liquid carrier and other excipients.
  • the herbicide composition comprises an aqueous liquid carrier.
  • the inventors have found that the use of a polar solvent improves the solubility of the nonanoate salt in the aqueous liquid carrier and as a result can provide herbicide compositions having high nonanoate salt loadings (e.g. 300 g/L or more). Accordingly, it will be understood that the aqueous liquid carrier dissolves/suspends the nonanoate salt and optionally one or more agriculturally acceptable excipients.
  • the aqueous liquid carrier comprises or consists of water.
  • the water may comprise potable water.
  • the amount of aqueous liquid carrier may be quantity sufficient (q.s.).
  • the herbicide composition comprises: a) between about 300 g/L to about 600 g/L ammonium nonanoate; b) between about 50 g/L to about 200 g/L polar solvent; and c) optionally between about 0.1 g/L to about 50 g/L of one or more herbicidally or agriculturally acceptable additives/excipients.
  • the herbicide composition may further comprise one or more herbicidally or agriculturally acceptable additives/excipients.
  • the additives/excipients may be selected from the group consisting of a carrier, an antifoaming agent, a nutrient source, a fragrant, a base, a co-solvent, a wetting agent, an emulsifier, a humectant, a desiccating agent, a binder, a sticking agent, a filler, an antifreeze, a dispersing agent, an emulsifier, a preservative, a stabilizer, a humectant, and a pH adjusting agent, or a combination thereof.
  • a carrier an antifoaming agent
  • a nutrient source a fragrant
  • a base a co-solvent
  • a wetting agent emulsifier
  • a humectant a desiccating agent
  • a binder a sticking agent
  • a filler an
  • the one or more herbicidally or agriculturally acceptable additive/excipient is a nutrient source e.g. the herbicide composition is a “weed-and- feed” composition.
  • the nonanoate salt controls (e.g. kills/eliminates) unwanted vegetation, fungi or algae whilst providing a nutrient source to the area (e.g. soil) for future plant growth.
  • the nutrient source comprises a fertiliser (e.g. a material that comprises one or more of a nitrogen source, phosphate source and a potassium source).
  • the concentration of one or more herbicidally or agriculturally acceptable additives/excipients in the herbicide composition may be between about 0.1 to about 50. In one embodiment, the concentration of one or more herbicidally or agriculturally acceptable additives/excipients in the herbicide composition (in g/L) may be at least about 0.1, 0.2, 0.5, 1, 2, 5, 10, 15, 20, 30, 40, 50, 100, 150, 200, 250, 300, 350, 400, 450 or 500.
  • the concentration of one or more herbicidally or agriculturally acceptable additives/excipients in the herbicide composition (in g/L) may be less than about 500, 450, 400, 350, 300, 250, 200, 150, 100, 50, 40, 30, 20, 15, 10, 5, 2, 1, 0.5, 0.2, or 0.1.
  • the concentration of herbicidally or agriculturally acceptable additives/excipients may be in a range provided by any two of these upper and/or lower values, for example, the concentration of one or more herbicidally or agriculturally acceptable additives/excipients in the herbicide composition (in g/L) may be between about 0.1 to about 30.
  • the concentration of one or more herbicidally or agriculturally acceptable additives/excipients in the herbicide composition may also be provided as a % w/w of the total weight of the composition.
  • the concentration of one or more herbicidally or agriculturally acceptable additives/excipients in the herbicide composition may be at least about 0.01, 0.02, 0.05, 0.1, 0.2, 0.5, 1, 1.5, 2, 3, 4, 5, 10, 15, 20, 25, 30, 35, 40, 45 or 50
  • the concentration of one or more herbicidally or agriculturally acceptable additives/excipients in the herbicide composition in g/L may be less than about 50, 45, 40, 35, 30, 25, 20, 15, 10, 5, 4, 3, 2, 1.5, 1, 0.5, 0.2, 0.1, 0.05, 0.02 or 0.01.
  • the concentration of herbicidally or agriculturally acceptable additives/excipients may be in a range provided by any two of these upper and/or lower values, for example, the concentration of one or more herbicidally or agriculturally acceptable additives/excipients in the herbicide composition (in % w/w of the total composition) may be between about 0.01 to about 3.
  • the herbicide composition may also further comprise one or more additional active agents.
  • the additional active agent be a herbicidal active agent.
  • the herbicidal active agent may be any active agent that is substantially water soluble.
  • the herbicide composition comprises less than about 10% w/w free nonanoic acid based on the total weight of the composition. In one embodiment, the herbicide composition is substantially free of nonanoic acid. In one embodiment, the nonanoate salt is the sole herbicidal active agent present in the composition.
  • the present inventors have surprisingly identified that the use of certain polar solvents not only improves the solubility of the nonanoate salt in the aqueous liquid carrier, but also provides herbicide compositions of a desirable lower viscosity, even at high nonanoate salt loadings (e.g. 200 g/L or more).
  • the herbicide composition has a dynamic viscosity.
  • dynamic viscosity refers to the compositions resistance to flow when an external force is applied, such as when using a rotational viscometer.
  • the viscosities of the herbicide composition referred to herein are based on measurements using a rotational viscometer at 20 rpm at a temperature of 20°C. While any suitable rotational viscometer can be used as understood by the person skilled in the art, one suitable viscometer is a Brookfield rotational viscometer with RV Spindle 2.
  • the dynamic viscosity of the compositions described herein is measured using a Brookfield rotational viscometer with RV Spindle 2 at 20 rpm.
  • the dynamic viscosity of the herbicide compositions described herein are below 500 mPa.s when measured at these conditions.
  • herbicide compositions of lower viscosity typically have a viscosity of less than about 500 mPa.s when measured using a rotational viscometer at 20 rpm and at a temperature of 20°C. At this viscosity, the compositions are pourable and have acceptable container pourability residues.
  • the herbicide composition has a dynamic viscosity (in mPa.s) of less than about 500, 400, 350, 300, 250, 200 or 100 when measured using a rotational viscometer at 20 rpm and at a temperature of 20°C.
  • the herbicide composition has a dynamic viscosity (in mPa.s) of at least about 10, 20, 30, 40, 50, 60, 70, 80, 90 or 100 when measured using a rotational viscometer at 20 rpm and at a temperature of 20°C.
  • the dynamic viscosity may be in a range provided by any two of these upper and/or lower values, for example between about 10 to about 500, or between about 10 to about 100.
  • the herbicide composition may also have a container pourability residue.
  • the container pourability residue highlights how much of the composition remains in a container following a pouring event.
  • a low container pourability residue indicates that most of the composition is able to be poured from a container, and that an excessive amount does not remain in the container.
  • the herbicide composition has a container pourability residue (R) of less than about 5.0% and rinsed container pourability (R’) residue of less than about 0.25% measured using the Collaborative International Pesticides Analytical Council (CIPAC) method MT 148 Handbook F, pages 348, 349.
  • CIPAC Collaborative International Pesticides Analytical Council
  • the inventors have identified that the herbicide compositions described herein having a viscosity below 500 mPa.s may provide better characteristics in terms of ease of pourability, re- suspension/dilution in water and/or ease of spray application, despite the herbicide composition having in some cases a high nonanoate salt loading (e.g. 200 g/L or more). In contrast, nonanoate salt compositions having viscosities higher than 500 mPa.s are often of paste-like consistency and difficult to pour.
  • the herbicide composition may have a solution stability in water where substantially no cream or sediment is present after 30 minutes when 5 mL of composition is mixed with 100 mL of water as measured using CIPAC MT 41.
  • the herbicide composition may have a maximum of 60 mL of foam after 1 minute when 14 mL of herbicide composition is mixed with 200 mL water as measured using CIPAC MT 47.2.
  • the herbicide composition may have a density (in g/mL) of between about 0.8 to about 1.0.
  • the herbicide composition may have a density (in g/mL) of at least about 0.8, 0.85, 0.9, 0.95, 0.96, 0.97, 0.98, 0.99 or 1.
  • the herbicide composition may have a density (in g/mL) of less than about 1, 0.99, 0.98, 0.97, 0.96, 0.95, 0.9, 0.85 or 0.8.
  • the density may be a range provided by any two of these upper and/or lower values, for example between about 0.9 to 1.
  • the herbicide compositions described herein may be further diluted.
  • the herbicide composition may be a concentrate (e.g. comprise a high loading of nonanoate salt, such as 300 g/L or more) and in some cases may require dilution with water into a formulation that is amenable to be sprayed.
  • a herbicide formulation comprising a diluted herbicide composition described herein.
  • the herbicide formulation may be a “ready-to-use” (RTU) formulation.
  • the herbicide formulation is a diluted herbicide composition.
  • the herbicide composition is diluted with water, for example potable water.
  • the concentration of nonanoate salt is also diluted.
  • the concentration of nonanoate salt in the herbicide formulation (in g/L) is at least about 0.1, 1, 2, 5, 10, 15, 20, 25, 30, 35, 40, 45 or 50. In one embodiment, the concentration of nonanoate salt in the herbicide formulation (in g/L) is less than about 50, 45, 40, 35, 30, 25, 20, 15, 10, 5, 2, 1 or 0.1.
  • the concentration of nonanoate salt may be in a range provided by any two of these upper and/or lower values, for example the concentration of nonanoate salt in the herbicide formulation (in g/L) may be between about 10 to about 50, between about 20 to about 40, or between about 25 to about 35.
  • the concentration of polar solvent is also diluted.
  • the concentration of polar solvent in the herbicide formulation (in g/L) is at least about 0.1, 0.2, 0.5, 1, 2, 5, 8, 10, 12, 15, 18, 20, 25, 30, 40 or 50.
  • the concentration of polar solvent in the herbicide formulation (in g/L) is less than about 50, 40, 30, 25, 20, 18, 15, 12, 10, 8, 5, 2, 1, 0.5, 0.2 or 0.1.
  • the concentration of polar solvent in the herbicide formulation may be in a range provided by any two of these upper and/or lower values, for example the concentration of polar solvent in the herbicide formulation (in g/L) may be between about 2 to about 20, or between about 5 to about 10.
  • the concentration of one or more herbicidally or agriculturally acceptable additives/excipients in the herbicide formulation may be between about 0.001 to about 10. In one embodiment, the concentration of one or more herbicidally or agriculturally acceptable additives/excipients in the herbicide formulation (in g/L) may be at least about 0.001, 0.002, 0.005, 0.01, 0.02, 0.05, 0.1, 0.15, 0.2, 0.3, 0.4, 0.5, 1, 1.5, 2, 2.5, 3, 3.5, 4, 4.5, 5, 6, 7, 8, 9 or 10.
  • the concentration of one or more herbicidally or agriculturally acceptable additives/excipients in the herbicide formulation (in g/L) may be less than about 10, 9, 8, 7, 6, 5, 4.5, 4, 3.5, 3, 2.5, 2, 1.5, 1, 0.5, 0.4, 0.3, 0.2, 0.15, 0.1, 0.05, 0.02, 0.01, 0.005, 0.002 or 0.001.
  • the concentration of herbicidally or agriculturally acceptable additives/excipients may be in a range provided by any two of these upper and/or lower values, for example, the concentration of one or more herbicidally or agriculturally acceptable additives/excipients in the herbicide formulation (in g/L) may be between about 0.001 to about 5.
  • a herbicide formulation comprising a) between about 10 g/L to about 50 g/L ammonium nonanoate; b) between about 1 g/L to about 20 g/L polar solvent; and c) optionally between about 0.001 g/L to about 5 g/L of one or more herbicidally or agriculturally acceptable additives/excipients.
  • a process of preparing a herbicide composition described herein comprising mixing together nonanoic acid, a polar solvent, an alkali reactant, and an aqueous liquid carrier and optionally one or more herbicidally or agriculturally acceptable additives/excipients under conditions effective to form the herbicide composition, wherein the nonanoic acid reacts with the alkali reactant upon mixing the to form a nonanoate salt.
  • the alkali reactant may be any suitable alkali that acts as a base for reacting with nonanoic acid to form the conjugate nonanoate salt.
  • the alkali reactant may be ammonium hydroxide which reacts with nonanoic acid to form ammonium nonanoate.
  • Other suitable alkali reactants may include potassium hydroxide which reacts with nonanoic acid to form potassium nonanoate, sodium hydroxide which reacts with nonanoic acid to form sodium nonanoate, and the like.
  • the alkali reactant is ammonium hydroxide, and the nonanoic acid reacts with the ammonium hydroxide upon mixing to form ammonium nonanoate.
  • the ammonium hydroxide may be provided as a solution, such as an ammonium hydroxide aqueous solution, the water component of which contributed to the total amount of aqueous liquid carrier present in the herbicide composition.
  • the process comprises forming an emulsion comprising an aqueous phase and an organic phase.
  • the process comprises mixing together nonanoic acid and the polar solvent to form an organic phase, and mixing the organic phase with an aqueous phase comprising the alkali reactant and aqueous liquid carrier under conditions effective to form the herbicide composition, wherein the nonanoic acid reacts with the alkali reactant upon mixing the organic phase with the aqueous phase to form the nonanoate salt; and wherein the organic phase or aqueous phase optionally comprises one or more herbicidally or agriculturally acceptable additives/excipients.
  • the process may comprise: a) mixing together nonanoic acid and the polar solvent to form an organic phase; b) mixing the alkali reactant and an aqueous liquid carrier (e.g. potable water) to form an aqueous phase; and c) adding the organic phase to the aqueous phase under conditions effective to from the herbicide composition.
  • aqueous liquid carrier e.g. potable water
  • one or more herbicidally or agriculturally acceptable additives/excipients can be mixed with the aqueous phase or organic phase, or both.
  • the organic phase may comprise one or more herbicidally or agriculturally acceptable additives/excipients.
  • the nonanoic acid is neutralised by the alkali reactant to form a substantially water soluble nonanoate salt.
  • the nonanoic acid is neutralised by a stoichiometrically equivalent amount of alkali reactant.
  • the polar solvent and nonanoic acid are mixed at an elevated temperature, for example at a temperature (in °C) of between 20 to about 50, for example between about 35 to about 45, to form the organic phase.
  • the polar solvent is first heated to the elevated temperature, and the nonanoic acid is subsequently added to the heated polar solvent and mixed at the elevated temperature, to form the organic phase.
  • the organic phase and aqueous phase is mixed at an elevated temperature. In one embodiment, the organic phase and aqueous phase is mixed at a temperature (in °C) of at least about 20, 22, 25, 30, 35, 40, 45 or 50. In one embodiment, the organic phase and aqueous phase is mixed at a temperature (in °C) less than about 50, 45, 40, 35, 30, 25, 22 or 20.
  • the organic phase and aqueous phase may be mixed at a temperature in a range provided by any two of these upper and or lower values, for example between about 20°C to about 50°C, or between about 35°C to about 45°C.
  • the organic phase is added slowly to the aqueous phase.
  • the neutralisation of nonanoic acid with a stoichoimetrically equivalent amount of ammonium hydroxide to form ammonium nonanoate may be exothermic, and the slow addition of the organic phase to aqueous phase assists in controlling the temperature of the reaction.
  • the organic phase and aqueous phase is mixed for a period of time (in minutes) of at least about 0.1, 0.5, 1, 2, 5, 10, 20, 30, 60, 90 or 120. In one embodiment, the organic phase and aqueous phase is mixed for a period of time (in minutes) of less than about 120, 90, 60, 30, 20, 10, 5, 2, 1, 0.5 or 0.1.
  • the mixing time may be in a range provided by any two of these upper and/or lower values, for example between about 1 minute to about 120 minutes, or between about 20 minutes to about 60 minutes.
  • the inventors have identified that the lower viscosity of the herbicide composition assists when containers needs to be filled after preparing the composition.
  • the herbicide composition is diluted with water. This may occur shortly after the composition is prepared or sometime later, such as prior to applying to unwanted vegetation, fungi or algae.
  • the herbicide composition described herein or diluted composition thereof can be used to control unwanted vegetation, fungi or algae.
  • a method of controlling unwanted vegetation, fungi or algae comprising applying a herbicidally effective amount of the herbicide composition described herein or a diluted composition thereof to an area affected or likely to be affected by the unwanted vegetation, fungi or algae.
  • the unwanted vegetation is an annual or perennial weed or grass.
  • the unwanted vegetation is selected from one or more of capeweed, chickweed, clover, cobbler pegs, crouch grass, crowsfoot, false heather, fat hen, fleabane, lambs tongue, couch grass; barnyard, grass nutgrass, paspalum, peppercress, plantain, potatoweed, slender celery, stinking roger, common storksbill, moss or liverwort.
  • the fungi is lichen.
  • the herbicide composition or diluted composition thereof may be applied to the unwanted vegetation, fungi or algae in an amount effective to kill or retard the growth of the unwanted vegetation, fungi or algae.
  • the area may be any crop, grass, garden, lawn or a surface such as paths, driveways, around sheds, roadsides, fencelines etc. that has unwanted vegetation, fungi or algae growing or residing on, around or therein. It will be appreciated there is essentially no limitation on the area being treated with the herbicide composition described herein or diluted composition thereof, and rather the area can be selected depending on whether or not the area is affected by or likely to be affected by unwanted vegetation, fungi or algae.
  • the herbicide composition described herein or diluted composition thereof may be used to stop the weed seed-set without substantially affecting crop yield and grain quality. This is called “croptopping”. Croptopping is timed for the weed growth stage to control weed seed set from survivors of normal incrop weed control. It can be used to control ‘escapes’ from other weed management treatments, as a late post- emergent salvage treatment, or for managing herbicide resistance. Late weed control may also reduce grain contamination.
  • a method of croptopping comprising applying the herbicide composition described herein or a diluted composition thereof to a crop area in an amount effective to substantially prevent weed seed-set.
  • the herbicide composition or diluted composition thereof is applied in an amount effective to deliver between about 5 kg to about 70 kg of nonanoic acid per ha of area.
  • the herbicide composition or diluted composition thereof is applied in an amount effective to deliver between about 10 kg to about 60 kg of nonanoic acid per ha of area. In one embodiment, the herbicide composition or diluted composition thereof is applied in an amount effective to deliver at least about 10, 15, 20, 25, 30, 35, 40, 45, 50, 55 or 60 kg of nonanoic acid per ha of area. In one embodiment, the herbicide composition or diluted composition thereof is applied in an amount effective to deliver less than about 60, 55, 50, 45, 40, 35, 30, 25, 20, 15 or 10 kg of nonanoic acid per ha of area. The amount of nonanoic acid delivered may be in a range provided by any two of these upper and/or lower values. In one embodiment, the herbicide composition or diluted composition thereof is applied in an amount effective to deliver between about 20 kg to about 50 kg of nonanoic acid per ha of area.
  • the herbicide composition or diluted composition thereof is applied in an amount effective to deliver between about 10 L to about 5000 L of composition per ha of area. In one embodiment, , the herbicide composition or diluted composition thereof is applied in an amount effective to deliver at least about 10, 20, 50, 100, 200, 300, 500, 800, 1000, 1500, 2000, 2500, 3000, 3500, 4000, 4500 or 5000 L of composition per ha of area. In one embodiment, the herbicide composition or diluted composition thereof is applied in an amount effective to deliver less than about 5000, 4500, 4000, 3500, 3000, 2500, 2000, 1500, 1000, 800, 500, 300, 200, 100, 50, 20 or 10 L of composition per ha of area. The amount of nonanoic acid delivered may be in a range provided by any two of these upper and/or lower values.
  • the herbicide composition or diluted composition thereof is reapplied to the area affected or likely to be affected by the unwanted vegetation, fungi or algae.
  • the herbicide composition or diluted composition thereof is reapplied to the area affected or likely to be affected by the unwanted vegetation, fungi or algae within 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14 days after the first application. In one embodiment, the herbicide composition or diluted composition thereof is reapplied to the area affected or likely to be affected by the unwanted vegetation, fungi or algae within 7 to 14 days after the first application. [0120] In one embodiment, the herbicide composition or diluted composition thereof is sprayed on an area affected or likely to be affected by the unwanted vegetation, fungi or algae.
  • the herbicide composition may be provided a part of a kit.
  • a kit comprising: a) the herbicide composition described herein or a diluted composition thereof; and b) a spray applicator.
  • the kit may further comprise instructions for use.
  • the herbicide composition was produced in a batch process by the following process.
  • Part A (Aqueous phase): A jacketed reaction vessel with cooling was charged with water. The ammonium hydroxide solution was mixed into the water to form an aqueous phase.
  • Part B Organic phase: -In a separate vessel the organic components were combined to form an organic phase.
  • the Rhodiasolv Polarclean Solvent was introduced to a vessel equipped with a propeller type stirrer and the temperature was maintained between 35-45°C.
  • d-Limonene was added and stirring commenced.
  • the required amount of pelargonic acid was added as the stirring continued.
  • Gensil 2000 was added and stirring continued.
  • Part C (Combine the phases): The mixed organic phase was slowly added to the aqueous phase as the aqueous phase was stirred. The temperature was maintained between 35-45 °C and the mixture is stirred for a further 30 minutes.
  • the herbicide composition of Table 1 had a dynamic viscosity of less than about 500 mPa.s when measured at a temperature of 20°C using a Brookfield RV rotational viscometer using Spindle 1 at 20 rpm.
  • the herbicide composition of Table 1 had a container pourability residue (R) ⁇ 5.0% and rinsed container pourability (R’) ⁇ 0.25% measured using the Collaborative International Pesticides Analytical Council (CIPAC) method MT 148 Handbook F, pages 348, 349.
  • CIPAC Collaborative International Pesticides Analytical Council
  • the herbicide concentrate prepared in Example 1 used Rhodiasolv Polarclean, a polar solvent hydrotrope, which was surprisingly discovered to significantly improve the solubility of ammonium nonanoate solutions, prevent undesirable viscosity and allow for stable ammonium nonanoate loadings to -440 g/L, all the while retaining the concentrates lower viscosity and pourability. Other solvents were also investigated.
  • Herbicide concentrates were prepared according to Example 1, but replacing the Rhodiasolv Polarclean with the following solvents outlined in Table 3
  • Test candidate formulations consisted of the herbicide composition of Example 1 at 70, 85 & 100 ml/L and commercial reference products Wipe Out Bio (360 g/L glyphosate) at 7 mL/L, Slasher (525 g/L nonanoic acid) at 70 ml/L and Cavalier (500 g/L Oxyflurofen) at 2 L/ha. Treatments were applied with a 2 meter small plot precision spray boom in a randomized complete block trial design with four replicates at a water rate of 980 L/ha. A summary of the test candidates and treatment list is provided in Table 4 below:
  • Herbicide efficacy was estimated as the total number of individual weed species present in each plot at each assessment.
  • the statistical package of ARM V 9.0 (Agricultural Research Manager) was used to analyze study data.
  • An ANOVA at the 95% confidence interval was used to assess data set. Data was transformed where required by either square root, arcsine or log.
  • DAA-A All treatments demonstrated a significant (p ⁇ 0.05) level of efficacy in comparison to the untreated control. Wipe Out Bio provided the greatest level of numerical control although this was not significantly (p ⁇ 0.05) different to any other treatment.
  • 17 DAA-A All treatments demonstrated a significant (p ⁇ 0.05) level of efficacy in comparison to the untreated control. Cavalier provided the greatest level of numerical control although this was not significantly (p ⁇ 0.05) different to any other treatment.
  • Test candidate formulations consisted of herbicide composition of Example 1 at 40, 55, 70, 85 & 100 ml/L and were compared to the commercial reference products of Round Up Bioactive (360 g/L glyphosate) at 7 mL/L, Slasher (525 g/L nonanoic acid) at 70 ml/L Treatments were applied with a 2 meter small plot precision spray boom in a randomized complete block trial design with four replicates at a water rate of 980 L/ha with two applications on a 14 day window.
  • Table 7 A summary of the test candidates and treatment list is provided in Table 7 below:
  • Treatments were replicated four (4) times.
  • the treatment list is provided in Table 8.
  • Herbicide efficacy was estimated as the total number of individual weed species present in each plot at each assessment.
  • the statistical package of ARM V 9.0 (Agricultural Research Manager) was used to analyze study data.
  • An ANOVA at the 95% confidence interval was used to assess data set. Data was transformed where required by either square root, arcsine or log.
  • DAA-A All treatments provided a significant (p ⁇ 0.05) level of efficacy in comparison to the untreated control. There was no significant (p ⁇ 0.05) treatment difference. Herbicide composition of Example 1 at 85 mL/L and Round Up Bioactive provided the greatest (although not significant) numerical control. [0164] 14 DAA-A: All treatments provided a significant (p ⁇ 0.05) level of efficacy in comparison to the untreated control. There was no significant (p ⁇ 0.05) treatment difference. Herbicide composition of Example 1 at 85 mL/L continued to provide the greatest (although not significant) numerical control.
  • DAA-A All treatments provided a significant (p ⁇ 0.05) level of efficacy in comparison to the untreated control.
  • 17 DAA-A herbicide composition of Example 1 at 70 & 85 mL/L provided a significantly greater level of efficacy than Slasher. There was no other treatment difference.
  • Herbicide composition of Example 1 provided an equivalent level of control to Round Up Biactive and Slasher on most weed species but Herbicide composition of Example 1 was superior for Fleabane and Nutgrass control at selected intervals. Herbicide composition of Example 1 offers an alternate mode of action group on difficult and or herbicide resistant/ sensitive weed species.

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Abstract

La présente divulgation concerne de manière générale des compositions herbicides comprenant de l'acide nonanoïque ou n'importe quel ester de sel de celui-ci qui peut être utilisé pour lutter contre la végétation, les champignons ou les algues indésirables, et des processus, des procédés, des utilisations, des kits et analogues pour lutter contre la végétation, les champignons ou les algues indésirables. En particulier, les compositions herbicides comprennent a) un sel nonanoate ; b) un solvant polaire ; et c) un support liquide aqueux, la composition herbicide ayant une viscosité dynamique inférieure à environ 500 mPa.s lorsqu'elle est mesurée à l'aide d'un viscosimètre rotatif à 20 tr/min et à une température de 20 °C.
PCT/AU2023/051009 2022-10-12 2023-10-12 Composition herbicide WO2024077353A1 (fr)

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Citations (6)

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Publication number Priority date Publication date Assignee Title
US20020068680A1 (en) * 2000-12-01 2002-06-06 Falcon Lab Llc Herbicidal solutions comprising fatty acid ammonium salts and dicarboxylic acid diesters and methods of using the same
US20060063678A1 (en) * 2004-09-17 2006-03-23 Monsanto Technology Llc Fast symptom glyphosate formulations
WO2010102102A1 (fr) * 2009-03-06 2010-09-10 Syngenta Participations Ag Formulations électrolytiques compatibilisées
JP2014091739A (ja) * 2012-11-02 2014-05-19 Maruwa Biochemical Co Ltd 脂肪酸を用いた効果的な除草技術
JP2016190832A (ja) * 2015-03-30 2016-11-10 丸和バイオケミカル株式会社 ペラルゴン酸を用いる効果的除草技術
WO2022038489A1 (fr) * 2020-08-17 2022-02-24 Hiteshkumar Anilkant Doshi Composition pesticide comprenant du soufre élémentaire et un sel de choline d'acide pélargonique

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020068680A1 (en) * 2000-12-01 2002-06-06 Falcon Lab Llc Herbicidal solutions comprising fatty acid ammonium salts and dicarboxylic acid diesters and methods of using the same
US20060063678A1 (en) * 2004-09-17 2006-03-23 Monsanto Technology Llc Fast symptom glyphosate formulations
WO2010102102A1 (fr) * 2009-03-06 2010-09-10 Syngenta Participations Ag Formulations électrolytiques compatibilisées
JP2014091739A (ja) * 2012-11-02 2014-05-19 Maruwa Biochemical Co Ltd 脂肪酸を用いた効果的な除草技術
JP2016190832A (ja) * 2015-03-30 2016-11-10 丸和バイオケミカル株式会社 ペラルゴン酸を用いる効果的除草技術
WO2022038489A1 (fr) * 2020-08-17 2022-02-24 Hiteshkumar Anilkant Doshi Composition pesticide comprenant du soufre élémentaire et un sel de choline d'acide pélargonique

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Title
ANONYMOUS: "GUIDANCE DOCUMENT FOR THE GENERATION AND EVALUATION OF DATA ON THE PHYSICAL, CHEMICAL AND TECHNICAL PROPERTIES OF PLANT PROTECTION PRODUCTS UNDER REGULATION (EC) No. 1107/2009", EUROPEAN COMMISSION - DIRECTORATE-GENERAL FOR HEALTH AND FOOD SAFETY - FOOD AND FEED SAFETY, INNOVATION PESTICIDES AND BIOCIDES, 21 October 2021 (2021-10-21), XP093160831, Retrieved from the Internet <URL:https://food.ec.europa.eu/document/download/ba0347f1-c401-4423-8a8d-f353a916daac_en?filename=pesticides_ppp_app-proc_guide_phys-chem-ana_chem-subst.pdf> *

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