Herbicide compositions based on nonanoic acid and nonenoic acid

Abstract

The present invention relates to a composition comprising saturated nonanoic acid or a salt of saturated nonanoic acid, at least one monounsaturated nonanoic acid and at least one emulsifier, a process for the preparation of said composition and the use of said composition in weed control applications.

Description

Summary of the Invention

[0001] This invention relates to a composition comprising saturated nonanoic acid and / or saturated nonanoate, at least one monounsaturated nonanoic acid and at least one emulsifier, a method for preparing said composition, and the use of said composition in weed control applications.

[0002] Pesticides are chemical substances used in agriculture to eliminate parasitic organisms (animals or plants) that damage crop plants and impair soil productivity and crop quality.

[0003] Plant protection products, also known as phytosanitary products, are specific types of pesticide products typically used for one or more of the following purposes: protecting plants or plant products from all harmful organisms or preventing their effects; influencing plant life processes (such as in cases affecting their growth with substances other than nutrients); protecting plant products; destroying weeds or parts thereof; or controlling or preventing unwanted plant growth. Plant protection products include herbicides or weed killers, which are substances used to control weeds.

[0004] Herbicides can act selectively or completely (non-selectively). The selectivity of herbicidal function depends primarily on the nature of the active ingredient, as well as its concentration, the method by which the herbicide is applied to the soil or plants, and even on the mechanical vehicle used to distribute the herbicide.

[0005] Herbicides applied to leaves may not only act locally, causing harmful effects on leaf tissues and buds, but also exert their effects through general mechanisms (systemic or metastatic herbicides) once the substance is absorbed and translocated to the plant's roots. Herbicides applied to soil act by directly damaging the root system or preventing seed germination.

[0006] Another classification divides herbicides into pre-emergence herbicides and post-emergence herbicides. Pre-emergence herbicides attack weeds during their seedling stage by stopping their growth before they can compete with crop species, while post-emergence herbicides eliminate weeds once they have established themselves. Pre-emergence herbicides often leave residues in the soil, which can be detrimental to the environment.

[0007] Fatty acid-based compositions for herbicidal applications are known in the literature. See, for example, patent applications WO 91 / 05471, WO 91 / 05472 and EP 0 868 849.

[0008] In particular, nonanoic acid is effective against a variety of annual and perennial weeds (both monocots and dicots), algae, and mosses. Its herbicidal action typically occurs after the weeds have sprouted, i.e., through contact with the leaves. Nonanoic acid usually acts as a desiccant by contacting the above-ground parts of the weeds to which the product has been applied.

[0009] As described in the WAASA Herbicide Handbook (January 1, 1998, pp. 55-57), commercially available nonanoic acid under the trade name "Scythe" is a contact, non-selective, broad-spectrum, foliar herbicide that can be used to actively control the growth of emerging green vegetation.

[0010] Furthermore, nonanoic acid leaves no residue and therefore does not pollute the land.

[0011] However, among the drawbacks associated with the use of nonanoic acid in herbicide applications, it can be mentioned that its control period against weeds is not long enough due to the regrowth of most weeds.

[0012] Similarly, concentrated fatty acid compositions are usually required to be formulated, which can be diluted in water before use and retain their herbicidal activity intact.

[0013] The resulting aqueous formulation must be stable and not exhibit phase separation so that it can be conveniently stored before use.

[0014] Specifically, US Patent 5,035,741 describes an aqueous emulsion obtained from a herbicide composition comprising 20% ​​to 80% of at least one fatty acid, 15% to 75% of a natural or synthetic oil, and 2% to 10% of an emulsifier. However, this composition requires the use of a natural or synthetic oil that exhibits low levels of toxicity, good herbicidal activity, and is inexpensive.

[0015] There is still a need to find alternative herbicide compositions that can be easily formulated while minimizing the addition of stabilizers and / or coadjuvants so that they can be rapidly diluted in water when needed to obtain a stable, ready-to-use, water-based emulsion, while maintaining their effectiveness in weed control applications.

[0016] The applicant has now unexpectedly discovered a composition that solves the aforementioned technical problem.

[0017] In particular, the applicant unexpectedly discovered that the compositions according to the invention have high stability and can be advantageously diluted in water to produce stable water-based emulsions that are unexpectedly highly effective as non-selective herbicides and unexpectedly exhibit a longer weed control period compared to commercially available nonanoic acid-based herbicides.

[0018] A first aspect of the present invention relates to a composition comprising:

[0019] (a) An aliphatic monocarboxylic acid mixture, the mixture comprising:

[0020] -Saturated nonanoic acid, and

[0021] - At least one monounsaturated nonanoic acid having formula (I):

[0022] CH3-(CH2) m -CH = CH-(CH2) n -COOH

[0023] The sum (m+n) equals 5, where m and n individually represent 0 or integers selected from 1, 2, 3, 4, and 5.

[0024] Based on the total weight of the saturated nonanoic acid and the monounsaturated nonanoic acid having formula (I), the monounsaturated nonanoic acid having formula (I) is present in an amount of 0.5% to 15% by weight, preferably 0.5% to 10% by weight, and more preferably 0.5% to 8% by weight.

[0025] (b) Emulsifiers.

[0026] The compositions according to the invention can be easily formulated and appropriately have high stability so that they can be advantageously stored and transported.

[0027] Furthermore, the compositions according to the invention are surprisingly effective as advantageous non-selective herbicides.

[0028] The compositions according to the present invention are typically liquid phases.

[0029] The composition according to the present invention preferably comprises:

[0030] (a) Based on the total weight of the composition, a mixture of aliphatic monocarboxylic acids comprising 10% to 85% by weight, said mixture comprising:

[0031] -Saturated nonanoic acid, and

[0032] - At least one monounsaturated nonanoic acid having formula (I):

[0033] CH3-(CH2) m -CH = CH-(CH2)n -COOH

[0034] The sum (m+n) equals 5, where m and n individually represent 0 or integers selected from 1, 2, 3, 4, and 5.

[0035] Based on the total weight of the saturated nonanoic acid and the monounsaturated nonanoic acid having formula (I), the monounsaturated nonanoic acid having formula (I) is present in an amount of 0.5% to 15% by weight, preferably 0.5% to 10% by weight, and more preferably 0.5% to 8% by weight.

[0036] (b) Based on the total weight of the composition, 5% to 40% by weight of emulsifier.

[0037] (c) Based on the total weight of the composition, 0% to 50% by weight of at least one solvent, and

[0038] (d) Water, by weight, from 0% to 30% based on the total weight of the composition.

[0039] If the composition according to the invention further comprises at least one solvent, then based on the total weight of the composition, the composition typically comprises 5% to 40% by weight of at least one solvent.

[0040] If the composition according to the invention also contains water, then the composition typically contains 5% to 20% water by weight, based on the total weight of the composition.

[0041] In a first embodiment of the present invention, the composition according to the present invention preferably comprises:

[0042] (a) Based on the total weight of the composition, 60% to 85% by weight of aliphatic monocarboxylic acids, said mixture comprising:

[0043] -Saturated nonanoic acid, and

[0044] - At least one monounsaturated nonanoic acid having formula (I):

[0045] CH3-(CH2) m -CH = CH-(CH2) n -COOH

[0046] The sum (m+n) equals 5, where m and n individually represent 0 or integers selected from 1, 2, 3, 4, and 5.

[0047] Based on the total weight of the saturated nonanoic acid and the monounsaturated nonanoic acid having formula (I), the monounsaturated nonanoic acid having formula (I) is present in an amount of 0.5% to 15% by weight, preferably 0.5% to 10% by weight, and more preferably 0.5% to 8% by weight.

[0048] (b) 15% to 40% emulsifier by weight, based on the total weight of the composition.

[0049] The composition of the first embodiment of the present invention more preferably comprises:

[0050] (a) Based on the total weight of the composition, 70% to 80% by weight of aliphatic monocarboxylic acids, said mixture comprising:

[0051] -Saturated nonanoic acid, and

[0052] - At least one monounsaturated nonanoic acid having formula (I):

[0053] CH3-(CH2) m -CH = CH-(CH2) n -COOH

[0054] The sum (m+n) equals 5, where m and n individually represent 0 or integers selected from 1, 2, 3, 4, and 5.

[0055] Based on the total weight of the saturated nonanoic acid and the monounsaturated nonanoic acid having formula (I), the monounsaturated nonanoic acid having formula (I) is present in an amount of 0.5% to 15% by weight, preferably 0.5% to 10% by weight, and more preferably 0.5% to 8% by weight.

[0056] (b) 20% to 30% emulsifier by weight, based on the total weight of the composition.

[0057] In a second embodiment of the invention, the composition according to the invention preferably comprises:

[0058] (a) Based on the total weight of the composition, 10% to 60% by weight of aliphatic monocarboxylic acid mixture, said mixture comprising:

[0059] -Saturated nonanoic acid, and

[0060] - At least one monounsaturated nonanoic acid having formula (I):

[0061] CH3-(CH2) m -CH = CH-(CH2) n -COOH

[0062] The sum (m+n) equals 5, where m and n individually represent 0 or integers selected from 1, 2, 3, 4, and 5.

[0063] Based on the total weight of the saturated nonanoic acid and the monounsaturated nonanoic acid having formula (I), the monounsaturated nonanoic acid having formula (I) is present in an amount of 0.5% to 15% by weight, preferably 0.5% to 10% by weight, and more preferably 0.5% to 8% by weight.

[0064] (b) Based on the total weight of the composition, 10% to 30% by weight of emulsifier.

[0065] (c) Based on the total weight of the composition, 10% to 40% by weight of at least one solvent, and

[0066] (d) 10% to 20% water by weight, based on the total weight of the composition.

[0067] The composition according to this embodiment of the invention more preferably comprises:

[0068] (a) Based on the total weight of the composition, 10% to 40% by weight of aliphatic monocarboxylic acid mixture, said mixture comprising:

[0069] -Saturated nonanoic acid, and

[0070] - At least one monounsaturated nonanoic acid having formula (I):

[0071] CH3-(CH2) m -CH = CH-(CH2) n -COOH

[0072] The sum (m+n) equals 5, where m and n individually represent 0 or integers selected from 1, 2, 3, 4, and 5.

[0073] Based on the total weight of the saturated nonanoic acid and the monounsaturated nonanoic acid having formula (I), the monounsaturated nonanoic acid having formula (I) is present in an amount of 0.5% to 15% by weight, preferably 0.5% to 10% by weight, and more preferably 0.5% to 8% by weight.

[0074] (b) Based on the total weight of the composition, 10% to 30% by weight of emulsifier.

[0075] (c) Based on the total weight of the composition, 10% to 40% by weight of at least one solvent, and

[0076] (d) 10% to 20% water by weight, based on the total weight of the composition.

[0077] According to one embodiment of the invention, saturated nonanoic acid can be used in the form of saturated nonanoate salt, typically in the form of saturated ammonium nonanoate salt.

[0078] The saturated nonanoic acid in the compositions according to the invention is generally produced from vegetable oils. Vegetable oils used to produce saturated nonanoic acid suitable for use in the compositions according to the invention are generally selected from sunflower oil; oils from the Brassicaceae family, such as *Crambe abyssinica*, *Brassica carinata*, and *Brassicanapus*; and oils from the Cardueae family, such as *Cynara cardunculus*. The saturated nonanoic acid in the compositions according to the invention is preferably produced from sunflower oil or artichoke oil.

[0079] The saturated nonanoic acid in the compositions according to the invention is advantageously produced by the oxidative cracking process of vegetable oils (preferably sunflower oil or artichoke oil), typically in the presence of one or more oxidizing agents, as described, for example, in patent EP 2 519 489. The oxidative cracking process of the vegetable oils is advantageously carried out in the absence of ozone.

[0080] The oxidative cracking process of vegetable oils is generally distinguished from the processes known in the art for producing saturated aliphatic monocarboxylic acids, particularly saturated nonanoic acid, such as the ozone decomposition process of rapeseed oil or tallow oil, or the hydroformylation process of olefins, particularly 1-octene.

[0081] The monounsaturated nonanoic acid of formula (I) in the composition according to the invention is typically produced from vegetable oils.

[0082] The aliphatic monocarboxylic acids of the compositions according to the present invention can be characterized using generally known techniques, typically by gas chromatography (GC), preferably in combination with mass spectrometry (MS) (GC-MS).

[0083] The monounsaturated nonanoic acid having formula (I) in the composition according to the invention is quantitatively determined by measuring the iodine value. The iodine value can be measured using commonly known techniques, typically according to the standard procedure stated in ASTM Method D1959-97.

[0084] Monounsaturated nonanoic acid having formula (I) is generally present in the form of a mixture of cis and trans isomers, preferably a mixture of cis and trans isomers of 4-, 5-, 6- and 7-nonenoic acid, wherein at least 50% by weight of the mixture typically comprises trans isomers of 5-, 6- and 7-nonenoic acid.

[0085] The aliphatic monocarboxylic acid mixture of the compositions according to the invention may contain at least one additional carboxylic acid, particularly an aliphatic carboxylic acid. Based on the total weight of the mixture, the aliphatic monocarboxylic acid mixture of the compositions according to the invention may contain up to 10%, preferably 1% to 5% by weight, at least one additional aliphatic carboxylic acid. Any additional aliphatic carboxylic acid (if present) is preferably a saturated aliphatic monocarboxylic acid selected from caprylic acid, capric acid, undecanoic acid, 10-undecanoic acid, lauric acid, myristic acid, palmitic acid, oleic acid, ricinoleic acid, and mixtures thereof.

[0086] The aliphatic monocarboxylic acid mixture of the compositions according to the present invention may contain at least one additional herbicide. Any additional herbicide is selected from glyphosate, sulfonylureas, carfentrazone-ethyl, their derivatives, and mixtures thereof.

[0087] Specific, non-limiting examples of herbicides include, for example, the following active ingredients: bensulfuron, pyrimisulfuron, chlorpyrifos, azimsulfuron, benfluralin, bensulfuron-methyl, bifenox, bispyrac-sodium, cyhalofop-butyl, cycloxidim, cyprosulfamide, clethodim, clodinafop-propargyl, and isosulfuron. Clomazone, Clopyralid, Cloquintocet-Mexyl, Greenmeron, Chlorfenapyr, Chlorsulfuron-methyl, Dazomet, Betaine, Dicamba, Quizalofop-P-ethyl, Pyrfluthrin, Dimethenamid-P, Ethofumesate, Ethoxysulfuron-methyl, Fenclorim, and other herbicides. Fenoxaprop-P-ethyl, pyrimisulfuron, fluazifop-P-butyl, flufenacet, fluroxypyr, foramsulfuron, glyphosate, glyphosate trimesium, glyphosate ammonium salt, haloxyfop-P, imazamox, imazosulfuron, iodosulfuron-methyl-sodium, iodobenzonitrile, isoproturon, isopropanol isoxaben, isoxaben Isoxaflutole, Cyclosulfuron-methyl, Mesosulfuron-methyl, Nifedipine, Benzimidone, Metam-sodium, Metazachlor, Solubilone, Metosulam, Metribuzin, Metsulfuron, Nicosulfuron, Orthosulfamuron, Propylene Oxadiargyl Oxasulfuron, ethoxysulfuron, penoxsulam, pethoxamid, picolinafen, pyrazosulfuron, propyzamide, flusulfuron, pyraflufen-ethyl, pyrazosulfuron, S-metolachlor, sulfosulfuron, tembotrione, terbusulfuron, methyl thiophenesulfuron, tralkoxydim, triasulfuron, bensulfuron, triflusulfuron-methyl, and tritosulfuron.

[0088] The emulsifier in the compositions according to the present invention typically comprises at least one surfactant selected from nonionic surfactants and amphoteric surfactants.

[0089] For the purposes of this invention, the term "nonionic surfactant" should be understood to mean a surfactant that is uncharged and comprises both hydrophilic and lipophilic portions.

[0090] The nonionic surfactant is preferably selected from alkoxylated alcohols, alkoxylated tristyrylphenols, polyethoxylated fatty acid esters, and polyethoxylated vegetable oils.

[0091] Examples of alkoxylated alcohols include, for example, ethylene oxide-propylene oxide copolymers such as ethylene oxide-propylene oxide block copolymers or ethylene oxide-propylene oxide random copolymers.

[0092] Examples of polyethoxylated fatty acid esters include, for example, polyethoxylated derivatives of at least a portion of sorbitan esters with at least one fatty acid selected from lauric acid, palmitic acid, stearic acid and oleic acid, particularly polyethoxylated derivatives of 3,6-sorbitan monoesters with oleic acid.

[0093] Specific, non-limiting examples of polyethoxylated derivatives of 3,6-sorbitan monoester and oleic acid include, for example, those containing 20 to 50 moles, more preferably 25 to 40 moles, of oxyethylene units.

[0094] Examples of polyethoxylated vegetable oils include, for example, aliphatic carboxylic acid triglycerides, particularly saturated and / or unsaturated aliphatic C... 14 -C 20 Polyethoxylated derivatives of carboxylic acids.

[0095] Specific, non-limiting examples of polyethoxylated derivatives of aliphatic carboxylic acid triglycerides include, for example, polyethoxylated castor oil.

[0096] The polyethoxylated castor oil preferably contains 20 to 50 moles, more preferably 25 to 40 moles of oxyethylene units.

[0097] The molar content of oxyethylene units in the polyethoxylated fatty acids and polyethoxylated vegetable oils of the compositions according to the present invention can be determined according to any method generally known in the art.

[0098] The nonionic surfactant suitable for use in the emulsifier of the composition according to the invention preferably has a hydrophilic-lipophilic balance (HLB) value greater than or equal to 12.

[0099] Hydrophilic-lipophilic balance (HLB) is a measure of the degree of hydrophilicity of an emulsifier.

[0100] The hydrophilic-lipophilic balance (HLB) value of the nonionic surfactant in the emulsifier used in the compositions according to the present invention is typically measured according to any method generally known in the art.

[0101] For the purposes of this invention, the term "amphoteric surfactant" should be understood to mean a surfactant that behaves as a cationic surfactant in an acidic environment or as an anionic surfactant in an alkaline environment.

[0102] The amphoteric surfactant is preferably selected from alkyl betaine.

[0103] Furthermore, the compositions according to the present invention may contain at least one organic solvent.

[0104] The organic solvents suitable for the compositions according to the present invention are generally selected from water-insoluble organic solvents.

[0105] Water-insoluble organic solvents are typically selected from aliphatic hydrocarbons, carboxylic acid esters (e.g., diesters of dicarboxylic acids or ester amides of dicarboxylic acids), alcohols, glycols, polyalkylene glycols, vegetable oils, and esters of vegetable oils.

[0106] A second aspect of the invention relates to a method for producing a composition according to the invention, the method comprising mixing a composition comprising, generally under stirring, the following:

[0107] (a) An aliphatic monocarboxylic acid mixture, the mixture comprising:

[0108] -Saturated nonanoic acid, and

[0109] - At least one monounsaturated nonanoic acid having formula (I):

[0110] CH3-(CH2) m -CH = CH-(CH2) n -COOH

[0111] The sum (m+n) equals 5, where m and n individually represent 0 or integers selected from 1, 2, 3, 4, and 5.

[0112] Based on the total weight of the saturated nonanoic acid and the monounsaturated nonanoic acid having formula (I), the monounsaturated nonanoic acid having formula (I) is present in an amount of 0.5% to 15% by weight, preferably 0.5% to 10% by weight, and more preferably 0.5% to 8% by weight.

[0113] (b) Emulsifiers.

[0114] Those skilled in the art will adjust the process conditions to obtain a uniform composition.

[0115] The composition used in the method according to the invention is as defined above.

[0116] A third aspect of the present invention relates to an aqueous emulsion comprising:

[0117] -The composition according to the invention, and

[0118] -Aqueous phase.

[0119] The water-based emulsion according to the invention is advantageously prepared by diluting the composition according to the invention in an aqueous phase.

[0120] The water-based emulsions according to the present invention typically comprise:

[0121] -Based on the total volume of the water-based emulsion, 0.1% to 10% by volume of the composition according to the invention, and

[0122] -Based on the total volume of the water-in-oil emulsion, the aqueous phase is 90% to 99.9% by volume.

[0123] The water-based emulsion according to the present invention preferably comprises:

[0124] -Based on the total volume of the water-based emulsion, 0.1% to 8% by volume of the composition according to the invention, and

[0125] -Based on the total volume of the water-in-oil emulsion, the aqueous phase is 92% to 99.9% by volume.

[0126] For the purposes of this invention, the term "emulsion" should be understood to mean a dispersion system consisting of two immiscible liquid phases stabilized by an emulsifier. An emulsion typically has two immiscible liquid phases, one of which is dispersed in the other as droplets typically with an average diameter of 0.5 μm to 100 μm.

[0127] Therefore, an emulsion is different from a mixture in which two immiscible liquid phases are separated from each other.

[0128] The water-in-oil emulsion according to the invention is advantageously an oil-in-water emulsion.

[0129] The aqueous phase typically contains water and, optionally, an organic solvent.

[0130] The aqueous phase is preferably composed of water.

[0131] The applicant unexpectedly discovered that the aqueous emulsions according to the invention are surprisingly stable over a wide temperature range (typically from 4°C to 30°C), with minimal addition of stabilizers and / or adjuvants, and can be advantageously stored. Indeed, no phase separation was observed in the aqueous emulsions according to the invention, whether over short or long periods.

[0132] The water-in-oil emulsion according to the present invention exhibits excellent herbicidal activity.

[0133] In particular, the water-in-oil emulsion according to the invention exhibits excellent non-selective herbicidal activity and is especially effective as a post-emergence herbicide.

[0134] Therefore, a fourth aspect of the present invention relates to the use of water-in-oil emulsions as herbicides.

[0135] According to one embodiment of the present invention, the water-in-oil emulsion can be used as a herbicide with dehydrating agent properties.

[0136] A fifth aspect of the invention relates to a method for preventing or inhibiting plant growth, the method comprising applying an emulsion according to the invention to the plant.

[0137] The water-in-oil emulsion according to the invention is typically applied to plants by spraying, usually targeting the base or leaves of the plant.

[0138] The following examples illustrate the invention in a non-limiting manner.

[0139] Material

[0140] The mixture (hereinafter referred to as "mixture A") comprises:

[0141] -Based on the total weight of saturated nonanoic acid and monounsaturated nonanoic acid having formula (I), 96.3% saturated nonanoic acid by weight, and

[0142] -Based on the total weight of saturated nonanoic acid and monounsaturated nonanoic acid having formula (I), 3.7% by weight of monounsaturated nonanoic acid having formula (I).

[0143] In the mixture referred to below as "mixture B", the saturated nonanoate of mixture A is esterified to produce an ammonium salt of saturated nonanoic acid. The resulting mixture B comprises:

[0144] -Based on the total weight of saturated nonanoic acid and monounsaturated nonanoic acid having formula (I), 96.3% saturated nonanoic acid by weight, and

[0145] -Based on the total weight of saturated nonanoic acid and monounsaturated nonanoic acid having formula (I), 3.7% by weight of monounsaturated nonanoic acid having formula (I).

[0146] The mixture (hereinafter referred to as "mixture C") comprises:

[0147] -Based on the total weight of saturated nonanoic acid and monounsaturated nonanoic acid having formula (I), 98.75% saturated nonanoic acid by weight, and

[0148] -Based on the total weight of saturated nonanoic acid and monounsaturated nonanoic acid having formula (I), 1.25% by weight of monounsaturated nonanoic acid having formula (I).

[0149] The mixture (hereinafter referred to as "mixture D") comprises:

[0150] -Based on the total weight of saturated nonanoic acid and monounsaturated nonanoic acid having formula (I), 97.5% saturated nonanoic acid by weight, and

[0151] -Based on the total weight of saturated nonanoic acid and monounsaturated nonanoic acid having formula (I), 2.5% by weight of monounsaturated nonanoic acid having formula (I).

[0152] The mixture (hereinafter referred to as "mixture E") comprises:

[0153] -Based on the total weight of saturated nonanoic acid and monounsaturated nonanoic acid having formula (I), 95.0% saturated nonanoic acid by weight, and

[0154] -Based on the total weight of saturated nonanoic acid and monounsaturated nonanoic acid having formula (I), 5.0% by weight of monounsaturated nonanoic acid having formula (I).

[0155] The saturated nonanoic acid in mixtures A to E was obtained through the oxidative cracking process of sunflower oil.

[0156] The mixtures A to E, having the monounsaturated nonanoic acid of formula (I), are in the form of a mixture of cis and trans isomers of 4-, 5-, 6-, and 7-nonenoic acid.

[0157] by A commercially available herbicide under a trade name, which contains 71.96% by weight saturated nonanoic acid and up to 100% by weight emulsifier (labeled as authorized by the Italian Executive Decree of February 26, 2016) (hereinafter referred to as "herbicide 1").

[0158] by Erbicida Professional is a commercially available herbicide containing 18.8% saturated nonanoic acid by weight and up to 100% emulsifier by weight (label 1 - Italian Ministry of Labour, Health and Social Policy registration number 12461 dated June 18, 2009) (hereinafter referred to as "herbicide 2").

[0159] Polyethoxylated castor oil (HLB: 13.2) containing 36 molar ethylene oxide units (hereinafter referred to as "emulsifier A").

[0160] Polyoxyethylenesorbitan monooleate (HLB: 15.0) containing 20 molar ethylene oxide units (hereinafter referred to as "emulsifier B").

[0161] Ethylene oxide (EO)-propylene oxide (PO) block copolymer (EO∶PO=70∶30) (hereinafter referred to as "emulsifier C").

[0162] C 12 -C 14 Alkyl dimethyl betaine (hereinafter referred to as "emulsifier D").

[0163] Methyl 5-(dimethylamino)-2-methyl-5-oxovalerate (hereinafter referred to as "solvent A").

[0164] It has the formula CH3OC(O)-(CH2) x A mixture of dimethyl dicarboxylic acid esters of -C(O)OCH3, where x represents 2, 3 or 4 (hereinafter referred to as "solvent B").

[0165] Propylene glycol (hereinafter referred to as "solvent C").

[0166] Example 1

[0167] The composition is prepared by mixing mixture A with emulsifier A.

[0168] The resulting composition comprises:

[0169] -Based on the total weight of the composition, 72% by weight of mixture A, and

[0170] - Based on the total weight of the composition, 28% by weight of emulsifier A.

[0171] Example 2

[0172] The composition was prepared according to the procedure described in Example 1, but emulsifier B was used as the emulsifier.

[0173] The resulting composition comprises:

[0174] -Based on the total weight of the composition, 72% by weight of mixture A, and

[0175] - Based on the total weight of the composition, 28% by weight of emulsifier B.

[0176] Example 3

[0177] The composition is prepared by mixing mixture A with emulsifier C, solvent A and water.

[0178] The resulting composition comprises:

[0179] -Based on the total weight of the composition, 20% of mixture A by weight,

[0180] -Based on the total weight of the composition, 30% by weight of emulsifier C,

[0181] -Based on the total weight of the composition, 30% by weight of mixture A, and

[0182] -Based on the total weight of the composition, 20% water by weight.

[0183] Example 4

[0184] The composition is prepared by mixing mixture A with emulsifier C, solvents B and C, and water.

[0185] The resulting composition comprises:

[0186] -Based on the total weight of the composition, 20% of mixture A by weight,

[0187] -Based on the total weight of the composition, 20% emulsifier C by weight.

[0188] -Based on the total weight of the composition, 20% solvent B by weight.

[0189] -Based on the total weight of the composition, 20% solvent C by weight, and

[0190] -Based on the total weight of the composition, 20% water by weight.

[0191] Example 5

[0192] The composition is prepared by mixing mixture B with emulsifier D and water.

[0193] The resulting composition comprises:

[0194] -Based on the total weight of the composition, 30% of mixture B by weight,

[0195] -Based on the total weight of the composition, 10% by weight of emulsifier D, and

[0196] -Based on the total weight of the composition, 60% water by weight.

[0197] Example 6

[0198] The composition was prepared according to the procedure described in Example 1, but using mixture C.

[0199] Example 7

[0200] The composition was prepared according to the procedure described in Example 1, but using mixture D.

[0201] Example 8

[0202] The composition was prepared according to the procedure described in Example 1, but mixture E was used.

[0203] The compositions according to Examples 1 to 8 of the present invention have high stability and can be advantageously diluted in water to produce stable water-based emulsions.

[0204] Specifically, the compositions of Examples 1 to 8 were diluted in water to obtain a stable water emulsion, and the final concentration of the water emulsion was 8% by volume based on the total volume of the water emulsion.

[0205] Specifically, the stability of the water-in-water emulsions of Examples 1 and 2 was tested at 20°C at different time intervals (after 10 minutes, 30 minutes, 1 hour, and 24 hours of dilution in water under the above conditions) according to CIPAC standard method MT 36.

[0206] When no phase separation is observed, the water-in-oil emulsion is considered stable.

[0207] The results are shown in Table 1.

[0208] Comparative Example 1

[0209] An aqueous composition was prepared by diluting herbicide 1 in water, resulting in a final concentration of 8% by volume based on the total volume of the aqueous composition.

[0210] The stability of the water-in-oil emulsion of Comparative Example 1 was tested at 20°C at different time intervals (10 minutes, 30 minutes, 1 hour and 24 hours after dilution in water under the above conditions) according to CIPAC standard method MT 36.

[0211] The results are shown in Table 1.

[0212] Table 1

[0213]

[0214] As the results listed in Table 1 show, the aqueous emulsions according to the invention, such as those obtained, for example, from the compositions of each of Examples 1 and 2 according to the invention, are unexpectedly stable at 20°C and no phase separation was observed even after dilution in water for 24 hours.

[0215] The water-based emulsion according to the invention can be advantageously stored before use.

[0216] In contrast, the aqueous composition of Comparative Example 1 adversely exhibited phase separation after being diluted in water for only 10 minutes.

[0217] Furthermore, the herbicidal activity of the composition according to Example 1 of the present invention was tested on monocotyledonous plants such as foxtail grass (Setaria viridis (L.) Beauv.) and compared with the herbicidal activity of herbicide 1.

[0218] Finally, the herbicidal activity of the compositions according to Examples 3 to 5 of the present invention was tested on monocotyledonous plants such as foxtail grass and barnyard grass (Echinochloa crus-galli (L.) Beauv.) and dicotyledonous plants such as black nightshade (Solanum nigrum L.) and compared with the herbicidal activity of herbicide 2.

[0219] According to ED 50 Values ​​for evaluating herbicide effectiveness, ED 50 The value is the amount of herbicide [kg / ha] required to achieve a 50% reduction in plant growth.

[0220] The results are shown in Table 2.

[0221] Table 2

[0222]

[0223] As shown in Table 2, the composition of Example 1 according to the present invention exhibits greater herbicidal efficacy than herbicide 1. Furthermore, the compositions of Examples 3 to 5 according to the present invention exhibit greater herbicidal efficacy than herbicide 2.

[0224] Comparative Example 2

[0225] The composition was prepared by mixing saturated nonanoic acid with emulsifier A.

[0226] The resulting composition comprises:

[0227] -Based on the total weight of the composition, 72% saturated nonanoic acid by weight, and

[0228] - Based on the total weight of the composition, 28% by weight of emulsifier A.

[0229] The composition thus obtained is diluted in water to obtain a stable water emulsion with a final concentration of 8% by volume based on the total volume of the water emulsion.

[0230] The herbicidal activity of the compositions according to Examples 6 to 8 of the present invention was tested on dicotyledonous plants such as Artemisia vulgaris L. and Potentilaria lareptans L., and compared with the herbicidal activity of the composition of Comparative Example 2 which does not contain monounsaturated nonanoic acid.

[0231] Weed control effectiveness was evaluated based on the weight reduction of treated dry matter relative to untreated dry matter, using a field dose of 16 l / ha (300 l of water per hectare).

[0232] The study employed a split-plot experimental design with three replicates, each replicate consisting of 20m units. 2 The three zones are represented. To quantify the herbicidal efficacy of the composition, all treatments were sprayed on Artemisia argyi and Potentilla chinensis using a backpack sprayer under open field conditions at 2 to 3 leaf growth stages. For each topic, the aboveground biomass of each weed was harvested at 7 and 12 DAA (days after application), dried at 105 ± 1 °C until constant weight, and weighed to determine the dry matter (DM) content and dry weight of the above samples.

[0233] The greater the weight reduction of the treated dry matter relative to the untreated dry matter after 7 days, preferably after 12 days, the higher the weed control effectiveness.

[0234] The results are shown in Table 3.

[0235] As shown in Table 3, the compositions of any one of Examples 6, 7 and 8 of the present invention unexpectedly exhibited a longer period of weed control compared to the composition of Comparative Example 2.

[0236] Table 3

[0237]

Claims

1. A herbicide composition comprising: (a) from 10% to 85% by weight, based on the total weight of the composition, of a mixture of aliphatic monocarboxylic acids, the mixture comprising: - saturated nonanoic acid, and - at least one monounsaturated nonanoic acid of formula (I): CH3-(CH2) m -CH=CH-(CH2) n -COOH Formula (I) wherein m + n equals 5, wherein m and n individually represent 0 or an integer selected from 1, 2, 3, 4 and 5, wherein the monounsaturated nonanoic acid of formula (I) is present in an amount of from 1.25% to 5.0% by weight, based on the total weight of the saturated nonanoic acid and the monounsaturated nonanoic acid of formula (I), (b) from 5% to 40% by weight, based on the total weight of the composition, of an emulsifier, the emulsifier comprising at least one surfactant selected from non-ionic surfactants and amphoteric surfactants, (c) from 0% to 50% by weight, based on the total weight of the composition, of at least one organic solvent, and (d) from 0% to 30% by weight, based on the total weight of the composition, of water.

2. The herbicide composition according to claim 1, the composition comprising: (a) from 60% to 85% by weight, based on the total weight of the composition, of the mixture of aliphatic monocarboxylic acids, and (b) from 15% to 40% by weight, based on the total weight of the composition, of the emulsifier.

3. The herbicide composition according to claim 1, the composition comprising: (a) from 10% to 60% by weight, based on the total weight of the composition, of the mixture of aliphatic monocarboxylic acids, (b) from 10% to 30% by weight, based on the total weight of the composition, of the emulsifier, (c) from 10% to 40% by weight, based on the total weight of the composition, of at least one organic solvent, and (d) from 10% to 20% by weight, based on the total weight of the composition, of water.

4. The herbicide composition according to any one of claims 1 to 3, wherein the non-ionic surfactant is selected from alkoxylated alcohols, alkoxylated tristyryl phenol, polyethoxylated fatty acid esters and polyethoxylated vegetable oils.

5. An aqueous emulsion comprising: - the herbicide composition according to any one of claims 1 to 4, and - an aqueous phase.

6. The aqueous emulsion according to claim 5, the aqueous emulsion comprising: - from 0.1 % to 10% by volume, based on the total volume of the aqueous emulsion, of the herbicide composition according to any one of claims 1 to 4, and - from 90% to 99.9% by volume, based on the total volume of the aqueous emulsion, of an aqueous phase.

7. Use of the aqueous emulsion according to claim 5 or 6 as a herbicide.

8. A method for controlling plants, the method comprising applying to the plants the aqueous emulsion according to claim 5 or 6.

9. A method for inhibiting the growth of plants, the method comprising applying to the plants the aqueous emulsion according to claim 5 or 6.

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