Herbicide compositions based on nonanoic acid

Abstract

The present invention relates to a concentrated emulsifiable composition comprising pelargonic acid and at least one emulsifier belonging to the class of anionic surfactants, preferably in acid form, at least one emulsifier belonging to the class of nonionic surfactants and at least an organic solvent, a process for preparing the composition and the use of the composition in herbicidal applications and as a desiccant harvesting aid. The composition is also advantageously used as a plant growth regulator.

Description

[0001] The project giving rise to the present invention was funded by the public-private Bio Based Industries Joint Undertaking within the European Union's Horizon 2020 research and innovation programme under grant agreement No 745012.

[0002] The present invention relates to a concentrated emulsifiable composition comprising pelargonic acid and at least one emulsifier belonging to the class of anionic surfactants, preferably in acid form, at least one emulsifier belonging to the class of nonionic surfactants and at least an organic solvent, a process for preparing said composition and the use of said composition in herbicidal applications.

[0003] The compositions are also advantageously used as plant growth regulators.

[0004] Plant protection products are generally intended for one of the following uses: to protect plants or plant products from all harmful organisms or to prevent the effects of such organisms, to influence important plant processes, e.g. substances other than nutrients that affect plant growth, to protect plant products, to destroy undesirable plants or plant parts, or to control or prevent the growth of undesirable plants. Plant protection products include herbicides or weed killer herbicides, which are substances used to control weeds.

[0005] Herbicides can be selective or complete (non-selective). The selectivity of the herbicidal action is essentially related to the nature of the active ingredient and also to its concentration, the way the herbicide is applied to the soil or plants, and even the mechanical tools used for its distribution.

[0006] Herbicides applied to foliage may act locally by damaging leaf tissue and buds, or by a general mechanism following absorption and transport of the substance to the roots of the plant (systemic or transport herbicides). Herbicides applied to the soil act by directly damaging the root system or by preventing seed germination.

[0007] Another classification divides herbicides into pre-emergence herbicides, which target weeds at the seedling stage and inhibit their development before they can compete with crops, and post-emergence herbicides, which inhibit weeds that have already developed. Pre-emergence herbicides tend to leave residues in the soil, which can be environmentally unfavorable.

[0008] Compositions based on fatty acids for herbicide applications are known from the literature, see, for example, patent applications WO 91 / 05471 and WO 91 / 05472 (Safer Inc.), EP 0 868 849 (W. Neudorff GmbH KG).

[0009] In particular, pelargonic acid (nonanoic acid) is active against a broad spectrum of annual and perennial weeds, monocots and dicots, algae and mosses. Its herbicidal activity is generally post-emergence weed control, i.e. contact activity at the leaf level. Pelargonic acid is often used as a contact desiccant for the aerial parts of weeds to which the product is applied.

[0010] As described in the WAASA Herbicide Manual (January 1, 1998, pages 55-57), the trade name The commercially available nonanoic acid is a non-selective, broad-spectrum foliar herbicide that can be used to control plant growth during the emergence period.

[0011] Pelargonic acid does not have any residual effect, which has some disadvantages, such as insufficient long-term control of weeds and possible regrowth of weeds.

[0012] Furthermore, one of the problems associated with the use of pelargonic acid as a herbicide is related to the high dosages required to achieve the desired effect, which makes its use outdoors difficult and uneconomical.

[0013] For example, the trademark name is A commercial herbicide formulation of ANTIQUIDA® contains 18.8 wt% pelargonic acid, diluted in water at a rate of 20 L of product per 100 L of water (as per label instructions), and applied to the field at a rate of 170 L of product per hectare, requiring approximately 830 L / hectare of water.

[0014] In order to reduce the required volume, it is usually necessary to formulate more concentrated nonanoic acid compositions which can be diluted in water before use and which retain their herbicidal activity. The resulting diluted compositions are usually prepared in the form of emulsions. Such aqueous emulsions are usually characterized by low stability and may therefore exhibit phase separation and are therefore not suitable for effective distribution on weeds. In addition, the stability of such emulsions is highly dependent on temperature and water hardness, making them usable only under certain conditions.

[0015] In order to increase the stability of the emulsion, the above-mentioned concentrate composition usually contains an emulsifier.

[0016] For example, commercial preparations Containing 72% by weight of nonanoic acid and a co-formulant, it was diluted at 8% v / v in water and applied to the field at a dosage of 16 L / hectare. However, when emulsified in water at the application rate, the formulation showed extensive phase separation, which occurred immediately after preparation and even earlier the higher the temperature and hardness of the water used. The result was that it was difficult to distribute the product evenly in the field, even if it was prepared just before use.

[0017] Therefore, there is still a need to find nonanoic acid formulations characterized by high levels of active alternatives to those mentioned above, which can be diluted in water to obtain ready-to-use emulsions that are sufficiently stable to ensure full efficacy in herbicide applications.

[0018] The applicant has now found that the above technical problem can be solved by a concentrated emulsifiable composition, which, in addition to nonanoic acid, also contains at least one emulsifier belonging to the category of anionic surfactants, at least one emulsifier belonging to the category of nonionic surfactants and at least an organic solvent. In particular, the composition according to the invention can be advantageously diluted in water to produce an aqueous emulsion with good emulsion stability even at high concentrations of active ingredients. Surprisingly, the composition according to the invention applied in the form of an aqueous emulsion shows an increased efficacy as a comprehensive herbicide, which is significantly better than the commercial or literature-described nonanoic acid-based formulations, even at the same dose of the active ingredient used. Advantageously, the composition according to the invention can also maintain its efficacy for more than 2 to 4 weeks, depending on meteorological conditions, thereby allowing effective control of weeds over a sufficiently long period of time to prevent most weeds from growing again.

[0019] These properties also allow the amount of active ingredient required to obtain adequate control of weed development to be significantly reduced, thereby reducing the volume of formulation to be used in the field.

[0020] US 7,820,594 B2 discloses herbicidal compositions comprising pelargonic acid and anionic or nonionic surfactants which show effective weed control only in the first few days after treatment.

[0021] In a first aspect, the present invention relates to a composition comprising:

[0022] (a) 40% to 90% by weight of nonanoic acid; and

[0023] (b) up to 15% by weight of at least one emulsifier belonging to the class of anionic surfactants having formula (I)

[0024] (R-(OCHR1-CHR2) n -(OCHR3-CHR4) m -O-) q -Z

[0025] Where R is a linear or branched C4-C 18 alkyl,

[0026] R1, R2, R3 and R4 are independently H or CH3,

[0027] n and m are the same or different integers of 0 to 30 and at least one of n and m is not 0, q is 1 or 2,

[0028] Z represents a sulfate or phosphate group in acid form or a salt thereof,

[0029] (c) 5 to 55% by weight of at least one organic solvent,

[0030] (d) 1% to <15% by weight of at least one emulsifier belonging to the class of nonionic surfactants;

[0031] The weight ratio of the total amount of the anionic surfactant (b) and the nonionic surfactant (d) to the nonanoic acid is 0.05 to 0.15.

[0032] Surprisingly, it was found that, with the same amount of active ingredient distributed in the field, a ratio of the sum of anionic surfactant (b) and nonionic surfactant (d) relative to the weight content of pelargonic acid above 0.15 actually resulted in a reduction in the herbicidal activity of the composition.

[0033] The composition of the present invention comprises 40% to 90% by weight of nonanoic acid, preferably 40% to 85% by weight, more preferably 75% to 85% by weight of nonanoic acid, relative to the total weight of the composition.

[0034] The composition of the invention comprises >0% to 15% by weight of at least one emulsifier belonging to the class of anionic surfactants of formula (I). Preferably, the emulsifier belonging to the class of anionic surfactants of formula (I) is ≥0.5% by weight, ≥1% by weight, ≥2% by weight, ≥3% by weight, ≥4% by weight, ≥5% by weight and ≤15% by weight, ≤14% by weight, ≤13% by weight, ≤12% by weight, ≤11% by weight, ≤10% by weight, ≤9% by weight relative to the total weight of the composition. Preferably, the emulsifier belonging to the class of anionic surfactants of formula (I) is 3% to 13% by weight, more preferably 5% to 10% by weight relative to the total weight of the composition.

[0035] The composition according to the invention comprises from 5% to 55% by weight of at least one organic solvent, preferably from 5% to 40% by weight of at least one organic solvent, relative to the total weight of the composition.

[0036] The composition of the present invention comprises at least one emulsifier belonging to the class of nonionic surfactants. The total amount of emulsifiers belonging to the class of nonionic surfactants is from 1% to <15% by weight, preferably from 1% to 10% by weight, more preferably from 1% to 5% by weight, relative to the total weight of the composition.

[0037] The composition according to the invention is particularly advantageous when the content of anionic surfactant (b) is greater than 5% by weight, preferably from 10% to 60% by weight, relative to the total weight of anionic surfactant and nonionic surfactant.

[0038] The compositions according to the invention can be easily formulated to produce homogeneous solutions which conveniently have a high stability, so that they can be advantageously stored and transported.

[0039] When diluted in water in the application dosage, the composition according to the invention forms a stable emulsion even at high concentrations of pelargonic acid under different conditions of temperature and water hardness.

[0040] The compositions according to the invention also have a less noticeable odor than commercial preparations.

[0041] These compositions are also surprisingly effective as herbicides, advantageously having an all-around action.

[0042] The compositions according to the invention are generally in liquid form.

[0043] The nonanoic acid of the composition according to the invention is usually produced from a vegetable oil with a high oleic or erucic acid content. The vegetable oil used to produce the nonanoic acid that can be used in the composition according to the invention is usually selected from: sunflower oil, safflower oil, oils from the cruciferous family, such as Crambe abyssinica, Brassica carinata, Brassica napus (rapeseed), and oils from the genus Cirsium, such as Cardoon (thistle). The nonanoic acid of the composition according to the invention is preferably produced from high oleic sunflower oil.

[0044] The nonanoic acid of the composition according to the invention is generally produced by a process of oxidative cleavage of vegetable oils, preferably high oleic sunflower oil, in the presence of one or more oxidizing agents, as described, for example, in patent EP 2 519 489. The process of oxidative cleavage of vegetable oils is advantageously carried out in the absence of ozone.

[0045] The process of oxidative cleavage of vegetable oils is generally different from the processes generally known in the art for producing saturated aliphatic monocarboxylic acids, especially nonanoic acid, such as, for example, the ozonolysis of rapeseed oil or tallow oil or the hydroformylation of olefins, especially 1-octene.

[0046] The composition according to the invention may contain nonanoic acid mixed with other aliphatic monocarboxylic acids. In such a case, the aliphatic monocarboxylic acid is advantageously present in an amount of 0.5% to 15% by weight, preferably 0.5% to 10% by weight, more preferably 0.5% to 8% by weight, relative to the weight of nonanoic acid. The aliphatic monocarboxylic acids other than nonanoic acid, if present, are preferably chosen from:

[0047] - saturated aliphatic monocarboxylic acids, preferably selected from the group consisting of caprylic acid, capric acid, undecanoic acid, 10-undecenoic acid, lauric acid, myristic acid, palmitic acid, oleic acid, ricinoleic acid and mixtures thereof;

[0048] - a monounsaturated aliphatic monocarboxylic acid, preferably a monounsaturated 9-carbon carboxylic acid of formula (II): CH3-(CH2) m -CH=CH-(CH2) n -COOH

[0049] wherein the sum (m+n) is equal to 5, wherein m and n individually represent 0 or an integer selected from 1, 2, 3, 4 and 5, as described, for example, in patent application WO 2019 / 030060;

[0050] - an aliphatic keto acid having the formula (III): RC(O)-(CH2) n -COOH

[0051] wherein R represents H or alkyl, preferably C1-C5 alkyl, more preferably C1-C4 alkyl, and n represents 0, 1 or 2, as described, for example, in patent application WO 2019 / 030062.

[0052] The composition according to the invention may comprise at least one additional herbicide. Any additional herbicide is preferably selected from glyphosate, sulfanilurea, carfentrazone ethyl, their derivatives and mixtures thereof.

[0053] Non-limiting specific examples of herbicides include, for example, the following active ingredients: fenthiocarb, amidosulfuron, aminopyralid, tetrazosulfuron, fluazifop, benzylsulfuron, cypermethrin, bispyrac-sodium, cyhalofop-butyl, ciclosulfim, ciprosulfamide, clethodim, clodinafop-butyl, isoflurane, chlorpyrifos-butyl ... Chlorothione, Clopyralid, Quinoline-mexyl, Chlorotoluron, Chlorprofam, Chlorosulphon, Dazomethane, Betaine, Dicamba, Diclofenac, Difluanid, Fenchlorim-P, Etofumesate, Ethoxysulfuron, Fenchlorim, Azofenac, pyrimidinesulfuron, bispyribac, pyrifos-butyl, flufenacet, fluroxypyr, foramsulfuron, glyphosate, glyphosate trimesium, ammonium glyphosate, flupyralid, imazamox, pyrazosulfuron, iodosulfuron sodium, ioxinil, isoproturon, iso Amid Mesotrione, cypermethrin, mesotrione, metamitron, Metam Na, Methazachlor, sulfamethoxam, metribuzin, metsulfuron-methyl, nicosulfuron, pyrimidinesulfuron, acetylene Herbicide, Pendimethalin, oxasulfuron, oxyfluorfen, pendimethalin, penoxsulam, pethosulfuron, pyraclostrobin, pyraclostrobin, propidium, prosulfuron, pyraclostrobin, sulfosulfuron, s-isopropylamine, sulfosulfuron, cyproconazole, terbuthion, tifensulfuron-methyl, avena citrate, tralcoxydim, bensulfuron-methyl, bensulfuron-methyl, fluazifop-methyl and trifloxysulfuron-methyl.

[0054] The emulsifier (b) of the composition according to the invention comprises at least one surfactant chosen from anionic surfactants of formula (I).

[0055] According to an advantageous aspect of the invention, only one of R1, R2, R3 and R4 is CH3.

[0056] According to another aspect, R1, R2, R3 and R4 are H. In other words, if one of n or m is 0, the substituents of the remaining repeating units (R1 and R2 or R3 and R4) are H.

[0057] Preferably, the emulsifier belonging to the class of anionic surfactants is selected from the group of anionic surfactants in acid form.

[0058] For the purposes of the present invention, the term "anionic surfactant in acid form" means a surfactant whose negative charge (anion) is neutralized by H+ ions. Preferably, Z represents a phosphate group.

[0059] The anionic surfactant is preferably selected from monoesterified and / or diesterified sulfuric acid and monoesterified and / or diesterified phosphoric acid, more preferably monoesterified.

[0060] The anionic surfactant is most preferably selected from, for example, mono- and di-[alkyl-polyethylene glycol] phosphates, mono- and di-[alkyl-polyethylene glycol] phosphates, mono- and di-[alkyl-polyethylene glycol] phosphates, mono- and di-[alkyl-polyethylene glycol] sulfates, mono- and di-[alkyl-polyethylene glycol] sulfates, mono- and di-[alkyl-polyethylene glycol] phosphates, mono- and di-[alkyl-polyethylene glycol] sulfates, and mixtures thereof. Even more preferred are: mono-[alkyl-polyethylene glycol-polypropylene glycol] phosphate, mono-[alkyl-polyethylene glycol] phosphate, mono-[alkyl-polyethylene glycol] sulfate. For example, mono-[hexadecyl-polyethylene glycol (10EO)-polypropylene glycol (5PO)] phosphate and di-[hexadecyl-polyethylene glycol (10EO)-polypropylene glycol (5PO)] phosphate, mono-[hexadecyl stearyl polyethylene glycol (11EO)] phosphate and di-[hexadecyl stearyl polyethylene glycol (11EO)] phosphate, sodium [dodecyltetradecyl polyethylene glycol (2EO)] phosphate. Even more preferred are mono-[hexadecyl polyethylene glycol (10EO)-polypropylene glycol (5PO)] phosphate and di-[hexadecyl polyethylene glycol (10EO)-polypropylene glycol (5PO)] phosphate.

[0061] In the present application, "EO" means a group -(OCHR1-CHR2)-, wherein R1=R2=H, and "PO" means a group -(OCHR3-CHR4)-, wherein R3 or R4=CH3.

[0062] The composition according to the invention may comprise one or more surfactants selected from nonionic surfactants (d).

[0063] For the purposes of the present invention, the term "nonionic surfactant" means a surfactant comprising a hydrophilic portion and a lipophilic portion which has no charge.

[0064] The nonionic surfactant is preferably selected from alkoxylated alcohols, tristyryl-phenols, alkoxylated fatty acid esters such as polyethoxylated fatty acid esters, polypropoxylated fatty acid esters and ethoxy-propoxylated fatty acid esters and polyethoxylated vegetable oils.

[0065] Examples of alkoxylated alcohols include ethylene oxide-propylene oxide copolymers, such as ethylene oxide-propylene oxide block copolymers or ethylene oxide-propylene oxide random copolymers.

[0066] Examples of alkoxylated fatty acid esters include, for example, at least partially alkoxylated derivatives of esters of sorbitan with at least one fatty acid selected from lauric acid, palmitic acid, stearic acid, oleic acid and ricinoleic acid, in particular polyethoxylated derivatives of esters of 3,6-sorbitan with C10 to C18 fatty acids or ethoxy-propoxylated derivatives of esters of 3,6-sorbitan with C10 to C18 fatty acids.

[0067] Non-limiting specific examples of the polyalkoxylated derivatives of 3,6-sorbitan monoester include, for example, those having a molar number of oxyalkylene units in the range of 10 to 50, more preferably 15 to 40.

[0068] Examples of polyalkoxylated vegetable oils include aliphatic carboxylic acids, especially saturated and / or unsaturated C 14 -C 20 Polyethoxylated derivatives of triglycerides of aliphatic carboxylic acids.

[0069] Non-limiting specific examples of polyalkoxylated derivatives of aliphatic carboxylic acid triglycerides include, for example, polyethoxylated castor oil.

[0070] Preferably, the molar number of oxyethylene units (EO) of the polyethoxylated castor oil is in the range of 20-50, more preferably 25-40.

[0071] According to one aspect of the invention, the composition is free of cationic surfactants.

[0072] The composition according to the invention comprises at least one organic solvent.

[0073] The organic solvents that can be used in the composition according to the invention are generally chosen from water-insoluble organic solvents.

[0074] The water-insoluble organic solvent is generally selected from aliphatic hydrocarbons, esters of carboxylic acids such as, for example, diesters of dicarboxylic acids or esteramides of dicarboxylic acids, alcohols, unmodified vegetable oils (triglycerides) and transesterified vegetable oils with C1-C4 lower alcohols. Preferably, the water-insoluble organic solvent is selected from the group of unmodified vegetable oils (triglycerides) and transesterified vegetable oils with C1-C4 lower alcohols. More preferably, the water-insoluble organic solvent is the transesterified vegetable oil with methanol. More preferably, the water-insoluble organic solvent is the methyl ester (biodiesel) of fatty acids. Even more preferably, the water-insoluble organic solvent is the biodiesel with methyl oleate as the main component.

[0075] The composition according to the invention advantageously consists, relative to the total weight of the composition:

[0076] (a) 40% to 90% by weight of nonanoic acid,

[0077] (b) >0 to 15 wt. %, preferably 3 to 13 wt. %, more preferably 5 to 10 wt. % of at least one emulsifier belonging to the class of anionic surfactants having formula (I)

[0078] (R-(OCHR1-CHR2) n -(OCHR3-CHR4) m -O-) q -Z

[0079] Where R is a linear or branched C4-C 18 alkyl,

[0080] R1, R2, R3 and R4 are independently H or CH3,

[0081] n and m are the same or different integers of 0 to 30 and at least one of n and m is not 0, q is 1 or 2,

[0082] Z represents a sulfate or phosphate group in acid form, or a salt thereof, preferably in acid form,

[0083] (c) 5 to 55 wt %, more preferably 5 to 40 wt %, of at least one organic solvent,

[0084] (d) 1% to <15% by weight, preferably 1% to 10% by weight, more preferably 1% to 5% by weight, of at least one emulsifier belonging to the class of nonionic surfactants;

[0085] The weight ratio of the total amount of the anionic surfactant (b) and the nonionic surfactant (d) to the nonanoic acid is 0.05 to 0.15.

[0086] According to a preferred aspect of the present invention, the composition according to the present invention preferably comprises or advantageously consists of the following, relative to the total weight of the composition:

[0087] (a) 40% to 85% by weight of nonanoic acid,

[0088] (b) 5 to 10% by weight of at least one emulsifier belonging to the class of anionic surfactants having formula (I)

[0089] (R-(OCHR1-CHR2) n -(OCHR3-CHR4) m -O-) q -Z

[0090] Where R is a linear or branched C4-C 18 alkyl,

[0091] R1, R2, R3 and R4 are independently H or CH3,

[0092] n and m are the same or different integers of 0 to 30 and at least one of n and m is not 0, q is 1 or 2,

[0093] Z represents a sulfate or phosphate group in acid form, or a salt thereof, preferably in acid form,

[0094] (c) 5 to 55% by weight of at least one organic solvent,

[0095] (d) 1 to 10% by weight of at least one emulsifier belonging to the class of nonionic surfactants;

[0096] The weight ratio of the total amount of the anionic surfactant (b) and the nonionic surfactant (d) to the nonanoic acid is 0.05 to 0.15.

[0097] According to a particularly preferred aspect of the present invention, the composition according to the invention preferably comprises or advantageously consists of the following, relative to the total weight of the composition:

[0098] (a) 40% to 85% by weight of nonanoic acid,

[0099] (b) 5 to 10% by weight of at least one emulsifier belonging to the class of anionic surfactants having formula (I)

[0100] (R-(OCHR1-CHR2) n -(OCHR3-CHR4) m -O-) q -Z

[0101] Where R is a linear or branched C4-C 18 alkyl,

[0102] R1, R2, R3 and R4 are independently H or CH3,

[0103] n and m are the same or different integers of 0 to 30 and at least one of n and m is not 0, q is 1 or 2,

[0104] Z represents a sulfate or phosphate group in acid form, or a salt thereof, preferably in acid form,

[0105] (c) 5% to 40% by weight of at least one organic solvent,

[0106] (d) 1 to 5% by weight of at least one emulsifier belonging to the class of nonionic surfactants;

[0107] The weight ratio of the total amount of the anionic surfactant (b) and the nonionic surfactant (d) to the nonanoic acid is 0.05 to 0.15.

[0108] The composition according to the invention may also contain 0% to 5% by weight of adjuvants relative to the total weight of the composition.

[0109] Adjuvants that may be present in the composition according to the invention are preservatives, dyes and odor improvers, defoamers, viscosity improvers and rheology modifiers. Examples of preservatives are 2-hydroxybiphenyl, sorbic acid, p-hydroxybenzaldehyde, methyl p-hydroxybenzoate, benzaldehyde, benzoic acid, propyl p-hydroxybenzoate and p-nitrophenol. Sorbic acid is preferred. Relative to the gross weight of the composition, the content of the preservative in the emulsion may be from 0.01% by weight to 1% by weight.

[0110] Odor improvers which may be used are fragrance oils.

[0111] The composition of the present invention may advantageously contain 0.1% to 5% by weight of viscosity improvers and rheology modifiers relative to the total weight of the composition. Examples of viscosity improvers and rheology modifiers are polyalkyl methacrylates in mineral or vegetable oils, synthetic esters with alkyl groups of different lengths (C1 to C18 and greater, linear or branched), natural rubber (polyisoprene) dissolved in vegetable oils or esters or mineral oils, polyolefins typically such as polyisobutylene, ethylene-propylene copolymers or poly-α-olefins, polycondensed fatty acids, polymer esters such as complex esters, chemically modified vegetable oils such as, for example, epoxidized oils, long chain esters (estolide) or polymerized vegetable oils, esters of rosin acid and polyalkylene glycols, hydroxyalkyl alkyl cellulose ethers, wherein the alkyl group contains 1 to 3 carbons and the hydroxyalkyl group contains 2 to 4 carbons, such as, for example, hydroxypropyl cellulose ethers or hydroxyethyl cellulose ethers. Hydroxyalkyl alkyl cellulose ethers are preferred.

[0112] The composition of the invention may advantageously comprise from 0.001% to 0.5% by weight of an antifoaming agent relative to the total weight of the composition. Examples of antifoaming agents are polyalkylene glycols, esters, ethylene oxide polymers in vegetable or mineral oils, polysiloxanes and acrylate polymers.

[0113] In a second aspect, the present invention relates to a process for producing a composition according to the present invention, said process comprising mixing:

[0114] (a) nonanoic acid, and

[0115] (b) at least one emulsifier belonging to the class of anionic surfactants having formula (I)

[0116] (R-(OCHR1-CHR2)n -(OCHR3-CHR4) m -O-) q -Z

[0117] Where R is a linear or branched C4-C 18 alkyl,

[0118] R1, R2, R3 and R4 are independently H or CH3,

[0119] n and m are the same or different integers from 0 to 30 and at least one of n and m is not 0,

[0120] q is 1 or 2,

[0121] Z represents a sulfate or phosphate group in acid form or a salt thereof,

[0122] (c) at least one organic solvent,

[0123] (d) at least one emulsifier belonging to the class of nonionic surfactants.

[0124] The mixing is generally carried out with stirring under process conditions such that a homogeneous composition is obtained.

[0125] In a third aspect, the present invention relates to an aqueous emulsion comprising:

[0126] - a composition according to the invention, and

[0127] - Aqueous phase.

[0128] The aqueous emulsions according to the invention are advantageously prepared by diluting the composition according to the invention in an aqueous phase.

[0129] The aqueous emulsion according to the invention generally comprises:

[0130] - 0.1% to 15% by volume of a composition according to the invention, relative to the total volume of the aqueous emulsion,

[0131] - 85% to 99.9% by volume of aqueous phase relative to the total volume of the aqueous emulsion.

[0132] The aqueous emulsion according to the invention preferably comprises:

[0133] - 0.5% to 12% by volume of a composition according to the invention, relative to the total volume of the aqueous emulsion,

[0134] - 88% to 99.5% by volume of aqueous phase relative to the total volume of the aqueous emulsion.

[0135] For the purposes of the present invention, the term "emulsion" means a dispersed system comprising two immiscible liquid phases stabilized by an emulsifier. An emulsion generally has two immiscible liquid phases, one dispersed in the other in the form of droplets typically having a median diameter of 0.5 μm to 10 μm.

[0136] Thus, an emulsion is distinguished from a mixture in which two immiscible liquid phases are separated from each other.

[0137] The aqueous emulsion according to the invention is advantageously an oil-in-water emulsion.

[0138] With commercial products In contrast, the aqueous emulsion according to the invention is stable for at least 24 hours and advantageously remains stable even after 24 hours after stirring for at least 30 minutes.

[0139] With commercial products In contrast, the aqueous emulsions according to the invention are stable over a wide temperature range (typically from 6°C to 30°C).

[0140] The aqueous emulsions according to the invention are stable under various water hardness conditions (typically 20 ppm to 342 ppm CaCO3).

[0141] Those skilled in the art will be able to readily assess the stability of an emulsion using known techniques, for example using the CIPAC MT36 standard.

[0142] According to the EPPO (European Plant Protection Organization) PP1 plant protection standard (Evaluation of the Efficacy of Plant Protection Products), the aqueous emulsions according to the invention exhibit excellent herbicidal activity.

[0143] In particular, the aqueous emulsions according to the invention exhibit excellent all-around herbicidal activity and are particularly effective as post-emergence herbicides. Therefore, in a fourth aspect the present invention relates to the use of the aqueous emulsion as a herbicide.

[0144] In particular, the direct application of aqueous emulsions to plants causes rapid drying of plant tissues by denaturing and disrupting the cuticle and plant cell membranes. This action results in a rapid release of cell sap, followed by dehydration and death of plant tissues affected by the non-selective contact effect.

[0145] According to one embodiment of the present invention, the aqueous emulsion can be used as a broad-spectrum herbicide with a drying effect, and can also be used as a pre-harvest adjuvant for crop drying (i.e., in potatoes and large-seeded beans). The composition according to the present invention can be used for weed control in grapevines, orchards and other fruit crops such as olives and nuts. In particular, the above-mentioned aqueous emulsion has been used as a broad-spectrum drying herbicide in grapevines and orchards. In these crops, weeds damage crop productivity by competing for plant resources including water, soil nutrients and light. In addition, in some cases, weeds hide and spread plant pests and pathogens. Conventional techniques for managing weeds in the above-mentioned crops require the application of pre-emergence herbicides and post-emergence herbicides and / or mechanical manipulation (also referred to as "tillage") under vineyards and orchard plants, while maintaining permanent plant ground cover between rows. The short-term effectiveness of residual herbicides such as glyphosate and frequent mechanical manipulation enables growers to successfully grow these crops and maintain productivity. However, concerns about the long-term consequences of conventional weed management have generated recent interest in alternative practices and / or the use of non-residual-acting herbicides that provide effective weed control while minimizing the negative environmental impacts associated with conventional weed management.

[0146] Taking into account the same dose of active ingredient, the efficacy of the composition according to the invention as a weed desiccant is higher than that of the commercial reference product In this application, the aqueous emulsions according to the invention are usually applied to the plants by means of a conventional boom sprayer designed specifically for under-row band herbicide applications.

[0147] In potatoes (Solanum tuberosum L.), the compositions according to the invention can be used as pre-harvest crop drying of aerial parts and / or stems of the plants without leaving the tubers to environmental conditions and being damaged. In conventional crop management, agents used as pre-harvest adjuvants are herbicides and / or defoliants, which artificially accelerate the drying of plant tissues, thereby facilitating mechanical harvesting of the crop.

[0148] From 4 May 2019, the main potato desiccant (containing diquat as active ingredient) has been banned and withdrawn from the market in the EU due to concerns related to exposure of bystanders and residents and its impact on bird life. In fact, the drying of potatoes before harvest is a common operation, either by mechanical destruction and / or by chemical drying using different active ingredients such as pyraclostrobin and nonanoic acid, with variable results from an efficacy point of view. Considering the same dose of active ingredient, the difference between the commercial reference product and the commercial reference product is not statistically significant. In comparison, the composition according to the invention showed a higher efficacy as a potato pre-harvest desiccant.

[0149] In a fifth aspect, the present invention relates to a method for controlling or inhibiting the growth of plants, the method comprising applying the aqueous emulsion according to the invention to the plants.

[0150] Indeed, the compositions according to the invention are also useful as plant growth regulators for controlling the growth of plants or parts thereof.

[0151] In particular, the aqueous emulsion has been used to control suckers in grapevines (Vitis vinifera L.) and to inhibit axillary shoots in tobacco plants (Nicotiana tabacum L.). In addition, as a plant growth regulator, the aqueous emulsion has also been evaluated as a blossom thinner for apples (Malus domestica Borkh).

[0152] In grapevines, the removal of shoots originating from the base of the stem (suckers) is a necessary operation, since suckers take away nutrients and energy from the productive parts of the plant and reduce ventilation of the bunches, leading to plant health problems. In traditional techniques, suckers are removed manually, mechanically or using residual chemical products with high environmental impact (glufosinate-ammonium). For the same dose of active ingredient, the use of the composition according to the invention in such sucker removal applications outperforms the commercial reference product efficacy.

[0153] In tobacco (a crop where leaves are the main product), the development of secondary shoots leads to the loss of nutrients required for leaf growth and product quality losses. Therefore, the removal of axillary shoots is an extremely important operation. In traditional technology, this operation is carried out manually (suckering), with high labor costs, or using chemical products (n-decanol, maleic hydrazide), which poses key operational and sustainability issues to the supply chain (long return times and pre-harvest intervals, impacts caused by the strong and persistent smell of n-decanol-based preparations).

[0154] The return time means the time that must elapse between the treatment and the return of the operator without wearing appropriate protection, while the pre-harvest interval means the minimum number of days that must elapse between the date of treatment with the plant growth regulator and the date of harvest of the treated product. For the same dose of active ingredient, the activity of the composition according to the invention in controlling axillary buds in tobacco is significantly superior to that of the commercial reference preparation. The activity obtained is of great significance from the perspective of modernizing the tobacco supply chain and significantly reducing to essentially eliminating the adverse effects associated with the persistent odor of n-decanol-based formulations.

[0155] The aqueous emulsions according to the invention are usually applied to plants by spraying. In use as a plant growth regulator, the spray should be directed to the main stem of the plant using a sprayer wand.

[0156] In apples, flower / fruit thinning is the removal of a portion of the flower and / or fruit crop before it matures on the tree, and is a necessary standard management procedure. In fact, too many fruit flowers and fruits on apple trees usually result in low-quality marketable products. Another problem is that the biennial fruit yield of apples is too large, and the alternate year yield is insufficient. This pattern can be broken, and a constant desired size yield can be obtained regularly by appropriate seedling thinning techniques. There are three commonly used flower / fruit thinning methods: mechanical, chemical and manual.

[0157] In manual operation, workers remove enough fruit to provide satisfactory fruit thinning. Manual thinning is a very labor-intensive and expensive technique. In recent years, machines for mechanical thinning of apple flowers have been developed. These machines use a series of knotted ropes that are dragged through the tree to knock off a portion of the flowers. In many cases, this practice causes considerable damage to the tree, and on some tree structures that must be suitable for the application of this technology, the thinning effect is insufficient. In addition, an increase in pests (such as aphids) and diseases has been noted on trees that have been thinned by machines. From a cost perspective, chemical thinning would be preferred, but environmental issues and inconsistent results are the main drawbacks of existing chemical methods. Inconsistent results include overthinning, underthinning, and leaf damage.

[0158] The success of a chemical fruit thinning strategy may depend on a variety of factors, including variety, tree condition, fruit set, proximity to pollinating trees, weather, active ingredient used, and the specific application protocol.

[0159] The activity of flower thinning in apples using the composition according to the invention was comparable to that of the commercial reference formulation Ethrel The activities obtained (with ethephon as the active ingredient) were comparable, which is significant from an efficacy standpoint considering that ethephon produces a very variable thinning response ranging from almost no thinning to complete inhibition of fruit set.

[0160] The following examples illustrate the invention for non-limiting purposes. Example

[0161] Material

[0162] - Nonanoic acid (98% purity by weight), obtained by oxidative cleavage of high oleic sunflower oil.

[0163] - Product name A commercially available herbicide formulation of , comprising pelargonic acid (72% by weight, corresponding to about 680 g / l active ingredient, without anionic and cationic surfactants) (label approved by Executive Decree of February 26, 2016).

[0164] - Emulsifier A (anionic surfactant): [hexadecyl-polyethylene glycol (10EO)-polypropylene glycol (5PO)] phosphoric acid,

[0165] -Emulsifier B (anionic surfactant): [cetyl stearyl polyethylene glycol (11EO)] Phosphoric acid ,

[0166] - Emulsifier C (anionic surfactant): [dodecyltetradecyl polyethylene glycol (2EO)] Sodium sulfate ,

[0167] - Emulsifier D (nonionic surfactant): sorbitan monooleate polyethoxylate (20EO),

[0168] - Emulsifier E (nonionic surfactant): sorbitan monooleate,

[0169] - Emulsifier F (nonionic surfactant): PEG-80 sorbitan laurate,

[0170] -Organic solvent A: fatty acid methyl esters, mainly including methyl oleate.

[0171] Example 1

[0172] The composition is prepared by mixing the following, relative to the total weight of the composition:

[0173] -80.7% by weight of nonanoic acid

[0174] - 6 wt% emulsifier A

[0175] - 3 wt% emulsifier D

[0176] -1 wt% emulsifier E

[0177] - 9.3 wt.% solvent A.

[0178] Example 2

[0179] The composition is prepared by mixing the following, relative to the total weight of the composition:

[0180] -80.7% by weight of nonanoic acid

[0181] - 6 wt% emulsifier B

[0182] - 3 wt% emulsifier D

[0183] -1 wt% emulsifier E

[0184] - 9.3 wt.% solvent A.

[0185] Example 3

[0186] The composition is prepared by mixing the following, relative to the total weight of the composition:

[0187] -80.7% by weight of nonanoic acid

[0188] - 6 wt% emulsifier C

[0189] - 3 wt% emulsifier D

[0190] -1 wt% emulsifier E

[0191] - 9.3 wt.% solvent A.

[0192] Comparative Example 4

[0193] Product name A commercially available herbicide formulation of PANOXYL ANTHRACITE® comprises pelargonic acid (72% by weight, corresponding to about 680 g / l active ingredient).

[0194] Comparative Example 5

[0195] The composition is prepared by mixing the following, relative to the total weight of the composition:

[0196] - 80% by weight of nonanoic acid

[0197] -5 wt% emulsifier D

[0198] -5 wt% emulsifier F

[0199] - 10% by weight of solvent A.

[0200] Example 6

[0201] The composition is prepared by mixing the following, relative to the total weight of the composition:

[0202] - 80% by weight of nonanoic acid

[0203] - 1 wt% emulsifier A

[0204] - 4 wt% emulsifier D

[0205] -5 wt% emulsifier F

[0206] - 10% by weight of solvent A.

[0207] Comparative Example 7

[0208] The composition is prepared by mixing the following, relative to the total weight of the composition:

[0209] -41% by weight of nonanoic acid

[0210] - 1 wt% emulsifier A

[0211] - 9 wt% emulsifier D

[0212] - 49% by weight of solvent A.

[0213] In the composition of Comparative Example 7, the ratio of the sum of the anionic surfactant (b) and the nonionic surfactant (d) to the weight content of nonanoic acid was 0.25, and thus higher than 0.15.

[0214] The compositions of Examples 1 to 3 have a relative humidity of 0.91 g / cm at ambient temperature. 3 The density of Example 6 and Comparative Example 5 at ambient temperature is 0.92 g / cm 3 Examples 1 to 3, Example 6 and Comparative Example 5 have an active ingredient concentration of about 720 g / l (ie, 100% nonanoic acid).

[0215] The composition of Comparative Example 7 has a thermal conductivity of 0.90 g / cm at ambient temperature. 3 and an active ingredient concentration of about 360 g / l (ie 100% nonanoic acid).

[0216] The compositions of Examples 1 to 3, Example 6, and Comparative Examples 4, 5, and 7 were diluted in water at different concentrations and tested:

[0217] - Emulsion stability (Example 8, Tables 2 to 4), evaluated on emulsions prepared by diluting the compositions of Examples 1 to 3 and Comparative Example 4 at 8% v / v and 10% v / v;

[0218] - Herbicidal activity of the diluted emulsions prepared by distribution in the field (Example 9, Tables 5 to 6):

[0219] o With 6.0% v / v and 7.55% v / v of the composition of Example 1 (doses of active ingredient are 8640 g / ha and 10880 g / ha),

[0220] ○ With 7.55% v / v of the composition of Examples 2, 3, 6 and Comparative Example 5 (the dosage of the active ingredient is 10880 g / hectare),

[0221] ○ With 8% v / v of the composition in Comparative Example 4 (the dosage of active ingredient is equal to 10880 g / hectare),

[0222] ○ 15.10% v / v of the composition of Comparative Example 7 (dosage of active ingredient equals 10880 g / hectare);

[0223] - Effectiveness in controlling tobacco buds by applying an emulsion prepared by diluting:

[0224] o With 0.6% v / v and 1% v / v of the composition of Example 1 (doses of active ingredient are 2592 g / ha and 4320 g / ha),

[0225] ○ The composition of Comparative Example 4 at 1.2% v / v (dosage of active ingredient equal to 4896 g / hectare);

[0226] - Effectiveness in controlling suckering in grapevines by applying an emulsion prepared by diluting:

[0227] ○ With 7.55% v / v of the composition in Example 1 (the dosage of active ingredient is 10880 g / hectare),

[0228] ○ The composition of Comparative Example 4 at 8% v / v (dosage of active ingredient equal to 10880 g / hectare);

[0229] - Effectiveness in weed control in apple orchards by applying an emulsion prepared by diluting:

[0230] o With 6.00% v / v and 7.55% v / v of the composition of Example 1 (doses of active ingredient are 8640 g / ha and 10880 g / ha),

[0231] ○ The composition of Comparative Example 4 at 8% v / v (dosage of active ingredient equal to 10880 g / hectare);

[0232] - Effectiveness as pre-harvest desiccant in potatoes by applying an emulsion prepared by diluting:

[0233] o With 6.00% v / v and 7.55% v / v of the composition of Example 1 (doses of active ingredient are 8640 g / ha and 10880 g / ha),

[0234] o The composition of Comparative Example 4 at 8% v / v (dosage of active ingredient equal to 10880 g / hectare).

[0235] Example 8. Comparison of emulsion stability

[0236] The stability of aqueous emulsions prepared from the compositions in Examples 1 to 3 and Comparative Example 4 was tested at different temperatures and using water of different hardness, according to standard CIPAC method MT36 (paragraph 36.1.1 - hand shaking) under the conditions indicated below. The stability of the 8% v / v and 10% v / v emulsions was tested in standard water A and D (characteristics given in Table 1) at 6°C, 20°C and 30°C and evaluated after 2 hours, 24 hours and finally after redispersion at 24 hours + 30 minutes, verifying in all tested conditions a better performance compared to the commercial product.

[0237] Table 1

[0238]

[0239] Table 1. Characteristics of the water standards used.

[0240] Table 2

[0241]

[0242] Table 2. ml of oil separated from 8% v / v emulsion in standard water D at 2 hours, 24 hours and 24 hours + 30 minutes at 20°C.

[0243] Table 3

[0244]

[0245] Table 3. ml of oil separated from 10% v / v emulsions in standard water A at 2 hours, 24 hours and 24 hours + 30 minutes at 6°C and 30°C.

[0246] Table 4

[0247]

[0248] Table 4. ml of oil separated from 10% v / v emulsions in standard water D at 2 hours, 24 hours and 24 hours + 30 minutes at 6°C and 30°C.

[0249] As shown in the results in Tables 2 to 4, the aqueous emulsion according to the present invention was more stable than the aqueous emulsion prepared by equal dilution of the herbicidal composition in Comparative Example 4, and no free oil separation was observed in the final evaluation (24 hours + 30 minutes after redispersion).

[0250] Example 9. Field test of herbicidal activity against natural infestations

[0251] The herbicidal activity of the aqueous emulsions prepared by Examples 1 to 3 and Example 6 was evaluated in a field whose flora composition mainly included dicotyledonous weeds (particularly Artemisia vulgaris L., Capsella bursa-pastoris, Taraxacum officinale and Medicago sativa L.) and monocotyledonous weeds (Cynodon dactylon and Poa pratensis) compared to the emulsions prepared by Comparative Examples 4, 5 and 7.

[0252] In order to test this activity against natural infestation, 7.55% v / v dilutions of the compositions in Examples 1 to 3, Example 6 and Comparative Example 5, 8% v / v of the composition in Comparative Example 4 and 15.10% v / v of the composition in Comparative Example 7 were prepared so that equal doses of active ingredient (10880 g / hectare) were distributed in the field using the same volume of aqueous emulsion. Specifically, 14.5 L / hectare of aqueous emulsions prepared from the compositions of Examples 1 to 3, Example 6 and Comparative Example 5, 16 L / hectare of aqueous emulsions prepared from the composition of Comparative Example 4 and 29.0 L / hectare of aqueous emulsions prepared from the composition of Comparative Example 7 were distributed.

[0253] The herbicidal activity was evaluated at four relevant times, 1 DAA (day after application), 3 DAA, 7 DAA and 12 DAA, and was carried out according to the standards defined by EPPO (Efficacy Evaluation of Plant Protection Products Standards PP1 / 152 (4), PP1 / 181 (4)).

[0254] Compared with the untreated control (equal to 0%), the visual efficacy assessment score (dry %) was assigned on a scale of 0% to 100%. The data related to the assessment of treatment effectiveness were statistically analyzed using the ANOVA test, and the mean values ​​were compared using the Tukey test, with a significance level of p≤0.05. The results are shown in Table 5.

[0255] Table 5

[0256]

[0257] Table 5. Herbicidal activity against natural infestations (0% to 100% visual rating); Tukey test a,b p≤0.05, n=3

[0258] The results obtained in the field tests show statistically that the aqueous emulsions prepared from Examples 1 to 3 and Example 6 have a greater herbicidal activity against monocotyledonous and dicotyledonous weeds than the aqueous emulsions prepared from Comparative Example 4 (containing no anionic and cationic emulsifiers), from Comparative Example 5 (containing no anionic emulsifiers) and from Comparative Example 7 (wherein the ratio of the sum of anionic surfactant (b) and nonionic surfactant (d) relative to the weight content of nonanoic acid is greater than 0.15). In particular, for the same dose of active ingredient used (10880 g / hectare) (Table 5), the herbicidal activity of the composition according to the invention is greater than 10% higher than the herbicidal activity of Comparative Examples 4 and 5 3 days after application, and greater than 17% higher after 12 days. In addition, the herbicidal activity of the composition according to the invention is greater than 40% higher than the herbicidal activity of Comparative Example 7 3 days after application, and greater than 50% higher after 12 days.

[0259] The same evaluation was carried out by repeating the test under naturally infested field conditions and comparing the herbicidal activity of two aqueous emulsions prepared from the composition in Example 1 diluted at 6% v / v and 7.55% v / v with an 8% v / v dilution prepared from the composition in Comparative Example 4.

[0260] In particular, the herbicidal activity was evaluated by distributing the active ingredient at a dosage of 8640 g / ha and 10880 g / ha (using 6% v / v and 7.55% v / v emulsions according to the present invention, respectively) and 10880 g / ha (using 8% v / v emulsion prepared from the formulation in Comparative Example 4) in the field. The results are shown in Table 6.

[0261] Table 6

[0262]

[0263] Table 6. Herbicidal activity against natural infestations (0% to 100% visual rating); Tukey test a,b p≤0.05, n=3

[0264] The results obtained in the field tests shown in Table 6 indicate that after the first 12 days after application, the herbicidal activity of the emulsion prepared from Example 1 was statistically higher than that of Comparative Example 4, even when 20% less active ingredient was used.

[0265] Example 10. Evidence of the effectiveness of tobacco bud control

[0266] The aqueous emulsion prepared by Example 1 was evaluated for efficacy in controlling tobacco buds on plants of the Virginia Bright variety and compared to the emulsion prepared by Comparative Example 4.

[0267] To test such efficacy on tobacco buds, two dilutions of the composition of Example 1 were prepared at 0.6% v / v and 1% v / v, and one dilution of 1.2% v / v of the composition of Comparative Example 4. In particular, efficacy was evaluated by applying 2592 g / ha and 4320 g / ha (using 0.6% v / v and 1% v / v emulsions according to the invention, respectively) and 4896 g / ha (using 1.2% v / v emulsion prepared from the formulation of Comparative Example 4) of active ingredient, respectively.

[0268] The tests were carried out according to EPPO PP standards 1 / 152 (4), 1 / 135 (4), 1 / 181 (4) and 1 / 155 (3). Three applications were made for each emulsion, one during the pre-flowering (A) period and two during the post-flowering (B, C) period.

[0269] To assess the effectiveness of axillary bud control in tobacco according to EPPO PP 1 / 155 (3), the number of live buds on a total of 5 terminal buds was counted at 4 relevant times. The results are shown in Table 7.

[0270] Table 7

[0271]

[0272] Table 7. Percentage of viable buds out of a total of 5 terminal buds detected 7 days after the first application (7DAA), 4 days after the second application (4DAB), 7 days and 13 days after the third application (7DAC and 13DAC), respectively (p≤0.05, Student-Newman-Keuls).

[0273] Although the emulsion prepared by Comparative Example 4 showed only moderate activity as a plant growth regulator, since after the third application, 82% to 84% of active shoots were still recorded on a total of five terminal buds (see 7DAC and 13DAC), the data recorded at the four relevant times show the surprising effectiveness of the 1% v / v emulsion according to the invention. The results are even more surprising if the concentration of active ingredient is taken into account, which is lower than in the comparison (1.2% v / v).

[0274] In particular, after the third application, the 1% v / v emulsion according to the invention showed unexpectedly high tobacco bud control, with only 28% of the total five terminal buds being active.

[0275] The 0.6% v / v emulsion according to the invention gave comparable results to the Comparative despite containing only about half the active ingredient.

[0276] Example 11. Evidence for the effectiveness of sucker control in grapevines

[0277] The efficacy of the aqueous emulsion prepared from Example 1 in controlling suckering in grapevines (grapes) was compared to the emulsion prepared from Comparative Example 4.

[0278] To test such efficacy, dilutions were prepared at 7.55% v / v of the composition from Example 1 and at 8.0% v / v of the composition from Comparative Example 4. In particular, efficacy was evaluated by applying 10880 g / hectare of active ingredient from two dilutions (dilutions from the composition from Example 1 and from Comparative Example 4).

[0279] The experiments were performed according to Good Experimental Practice (GEP). All evaluations and applications were performed according to the guidelines: EPPO Standards PP 1 / 152 (4), 1 / 135 (4), 1 / 181 (4), 1 / 161 (3) and 1 / 64 (4).

[0280] To evaluate the effectiveness of sucker control in grapevines according to EPPO PP 1 / 161 (3) (Control of suckers in grapevines), each emulsion was applied twice in the trial (the first application at the BBCH 55 phenological growth stage of the crop and the second application at the BBCH 67 stage).

[0281] Before the first application, uniform presence and development of active suckers were observed across the test plots. During the entire test period, the percentage of damaged and dead branches was recorded to assess sucker control. Sucker control activity was assessed at 22 DAB and 43 DAB at different relevant times.

[0282] A visual efficacy assessment score (% dryness) was assigned on a scale of 0% to 100% compared to the untreated control (equal to 0%).

[0283] Data from the evaluations were analyzed by analysis of variance (ANOVA). If a significant treatment effect was obtained (based on ANOVA analysis), differences between means were examined using the Student-Newman-Keuls (SNK) test (P=0.05).

[0284] The test results are shown in Table 8.

[0285] Table 8

[0286]

[0287] Table 8. Percentage of sucker control measured at 22 days after the second application (22 DAB) and 43 days after the second application (43 DAB), respectively (p≤0.05, Student-Newman-Keuls).

[0288] The data in Table 8 show that the aqueous emulsion prepared from Example 1 is more effective than the aqueous emulsion prepared from Comparative Example 4 (62.6% vs. 43.8% at 22 DAB and 44.8% vs. 36.2% at 43 DAB).

[0289] Example 12: Evidence of the effectiveness of weed control in apple orchards

[0290] The efficacy of the aqueous emulsion prepared by Example 1 in weed control in an apple orchard cv. Brookfield (apple) was compared with the emulsion prepared by Comparative Example 4. To test such efficacy, two dilutions of the composition of Example 1 at 6.00% v / v and 7.55% v / v, and one dilution of the composition of Comparative Example 4 at 8.00% v / v were prepared. In particular, efficacy was evaluated by applying 8640 g / ha and 10880 g / ha (using 6.00% v / v and 7.55% v / v emulsions according to the invention, respectively) and 10880 g / ha (using 8.00% v / v emulsion prepared from the formulation of Comparative Example 4) of active ingredient, respectively.

[0291] The trials were conducted in accordance with Good Experimental Practice (GEP). All evaluations and applications were conducted in accordance with the guidelines EPPO Standards PP1 / 152(4) (Design and Analysis of Efficacy Evaluation Trials), 1 / 135(4) (Phytotoxicity Evaluation), 1 / 181(4) (Conduct and Reporting of Efficacy Evaluation Trials) and 1 / 90(3) (Weeds in Orchards and Other Fruiting Tree Crops such as Citrus and Olives).

[0292] The trial was set up to evaluate the efficacy and selectivity of each emulsion against weeds in apple orchards. Two applications were made to BBCH 78 and BBCH 81 during crop phenological growth stages. At the first application, the weed population in the field was determined and the number of target weeds per square meter was recorded. The weed population in the field was uniform. The evaluation of herbicidal activity was carried out at four relevant times, at 7 DAA and 14 DAA and at 14 DAB and 20 DAB.

[0293] A visual efficacy assessment score (% dryness) was assigned on a scale of 0% to 100% compared to the untreated control (equal to 0%).

[0294] The test results are shown in Table 9.

[0295] Table 9

[0296]

[0297] Table 9. Percentage of herbicidal activity detected 14 days after the first application (14 DAA) and 14 days after the second application (14 DAB), respectively (p≤0.05, Student-Newman-Keuls).

[0298] These results clearly show that the emulsion according to the invention (Example 1) is more effective than the emulsion from Comparative Example 4 and that good control is ensured over a long period of time (at 14 DAB and 20 DAB) even at a lower concentration of active ingredient than the comparison (8640 g / ha for Example 1 versus 10880 g / ha for Comparative Example 4).

[0299] Example 13: Evidence of effectiveness as a pre-harvest desiccant in potatoes

[0300] The efficacy of the aqueous emulsion prepared by Example 1 as a pre-harvest desiccant was evaluated in potato cv. Mikado in comparison to the emulsion prepared by Comparative Example 4.

[0301] To test the activity, 6.0% v / v and 7.55% v / v dilutions of the composition from Example 1 and 8% v / v of the composition from Comparative Example 4 were prepared so that equal doses of active ingredient of 10880 g / ha for the 7.55% v / v dilution of the composition from Example 1 and 8% v / v of the composition from Comparative Example 4 were distributed in the field using the same volume of aqueous emulsion. In particular, 12.0 l / ha and 14.5 l / ha of the emulsion prepared from the composition of Example 1 and 16 l / ha of the emulsion prepared from the composition of Comparative Example 4 were distributed.

[0302] The evaluation of desiccant activity was carried out at 14 DAA (days after application) and was performed according to the criteria defined by the EPPO Guidelines PP n135(4) (Evaluation of phytotoxicity), PP n.143(3) (Desiccant for use on potatoes), PP n.152(4) (Design and analysis of efficacy evaluation trials) e PP n.181(4) (Conduct and reporting of efficacy evaluation trials).

[0303] Compared with the untreated control (equal to 0%), the visual efficacy assessment score (dry %) was assigned on a scale of 0% to 100%. The data related to the evaluation of treatment effectiveness were statistically analyzed using the ANOVA test, and the means were compared using the Tukey test, with a significance level of p≤0.05. The test results are shown in Table 10.

[0304] Table 10

[0305]

[0306] Table 10. Desiccant activity in potato crops (0% to 100% visual rating); Tukey testa,b p≤0.05,n=3

[0307] The results obtained in the field tests showed statistically that the desiccant activity of the aqueous emulsion prepared from Example 1 was also greater than the desiccant activity of the aqueous emulsion prepared from Comparative Example 4 at a lower active ingredient dosage of 8640 g / hectare for a 6.00% v / v dilution of the composition from Example 1.

Claims

1. A composition comprising: (a) 40% to 90% by weight of nonanoic acid; and (b) up to 15% by weight of at least one emulsifier belonging to the class of anionic surfactants having formula (I) (R-(OCHR1-CHR2) n -(OCHR3-CHR4) m -O-) q -FROM Where R is a linear or branched C4-C 18 alkyl, R1, R2, R3 and R4 are independently H or CH3, n and m are the same or different integers from 0 to 30 and at least one of n and m is not 0, q is 1 or 2, Z represents a sulfate or phosphate group in acid form or a salt thereof, (c) 5 to 55% by weight of at least one organic solvent, (d) 1 to 15% by weight of at least one emulsifier belonging to the class of nonionic surfactants; The weight ratio of the total amount of the anionic surfactant (b) and the nonionic surfactant (d) to the nonanoic acid is 0.05 to 0.

15.

2. The composition according to claim 1, comprising, relative to the total weight of the composition: (a) 40% to 85% by weight of nonanoic acid, (b) 5 to 10% by weight of at least one emulsifier belonging to the class of anionic surfactants having formula (I) (R-(OCHR1-CHR2) n -(OCHR3-CHR4) m -O-) q -FROM Where R is a linear or branched C4-C 18 alkyl, R1, R2, R3 and R4 are independently H or CH3, n and m are the same or different integers from 0 to 30 and at least one of n and m is not 0, q is 1 or 2, Z represents a sulfate or phosphate group in acid form or a salt thereof, (c) 5 to 55% by weight of at least one organic solvent, (d) 1 to 10% by weight of at least one emulsifier belonging to the class of nonionic surfactants; The weight ratio of the total amount of the anionic surfactant (b) and the nonionic surfactant (d) to the nonanoic acid is 0.05 to 0.

15.

3. The composition according to any one of claims 1 to 2, wherein the content of the anionic surfactant (b) is higher than 5% by weight relative to the total weight of the anionic surfactant and the nonionic surfactant.

4. The composition according to any one of claims 1 to 2, characterized in that The emulsifier (b) belongs to the class of anionic surfactants in acid form.

5. The composition according to any one of claims 1 to 2, characterized in that The anionic surfactant is selected from monoesterified phosphoric acid and diesterified phosphoric acid.

6. The composition according to any one of claims 1 to 2, characterized in that R1, R2, R3 and R4 are H.

7. The composition according to any one of claims 1 to 2, characterized in that Only one of R1, R2, R3 and R4 is CH3.

8. The composition according to any one of claims 1 to 2, characterized in that The emulsifier (b) is selected from the group consisting of mono-[alkyl-polyethylene glycol] phosphate ester / salt, mono-[alkyl-polyethylene glycol] phosphate ester / salt, and mono-[alkyl-polyethylene glycol] sulfate ester / salt.

9. The composition according to any one of claims 1 to 2, characterized in that The organic solvent is selected from aliphatic hydrocarbons; esters of carboxylic acids; alcohols; unmodified vegetable oils and ester-exchanged vegetable oils with C1-C4 lower alcohols.

10. The composition according to claim 9, characterized in that The carboxylic acid ester is a diester of a dicarboxylic acid or an ester amide of a dicarboxylic acid, and the unmodified vegetable oil is a triglyceride.

11. A method for producing a composition according to any one of claims 1 to 10, comprising mixing: (a) nonanoic acid, and (b) at least one emulsifier belonging to the class of anionic surfactants having formula (I) (R-(OCHR1-CHR2) n -(OCHR3-CHR4) m -O-) q -FROM Where R is a linear or branched C4-C 18 alkyl, R1, R2, R3 and R4 are independently H or CH3, n and m are the same or different integers from 0 to 30 and at least one of n and m is not 0, q is 1 or 2, Z represents a sulfate or phosphate group in acid form or a salt thereof, (c) at least one organic solvent, (d) at least one emulsifier belonging to the class of nonionic surfactants.

12. An aqueous emulsion comprising: - a composition according to any one of claims 1 to 10, and - Aqueous phase.

13. The aqueous emulsion according to claim 12, comprising: - 0.1% to 15% by volume of a composition according to any one of claims 1 to 10, relative to the total volume of the aqueous emulsion, - 85% to 99.9% by volume of aqueous phase relative to the total volume of the aqueous emulsion.

14. Use of the aqueous emulsion according to any one of claims 12 to 13 as a herbicide.

15. Use of an aqueous emulsion according to any one of claims 12 to 13 as a plant growth regulator for controlling the growth of plants or the growth of parts thereof.

16. A method for controlling or inhibiting the growth of plants, the method comprising applying to the plants an aqueous emulsion according to any one of claims 12 to 13.

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