SURFACTANT FOR AGRICULTURAL FORMULATIONS

2-Cotanol-derived surfactants address the challenge of wetting hydrophobic crop surfaces in agricultural formulations by reducing surface tension and improving stability, offering enhanced efficiency and environmental friendliness.

FR3153970A1Pending Publication Date: 2025-04-18ARKEMA FRANCE SA
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Patent Information

Application Number
FR2023011046
Authority / Receiving Office
FR · FR
Patent Type
Applications
Current Assignee / Owner
Filing Date
2023-10-13
Publication Date
2025-04-18
Patent Text Reader

Abstract

SURFACTANT FOR AGRICULTURAL FORMULATIONS The present invention relates to the use of at least one compound of formula (I): wherein R, A, B, n, and m are as defined in the description, as a surfactant in agrochemical formulations. The invention also relates to agrochemical formulations comprising said compound of formula (I). Fig.: none
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Description

Title of the invention: SURFACTANT FOR AGRICULTURAL FORMULATIONS

[0001] The present invention relates to the field of agriculture, in particular the field of nutrition and crop protection, and more particularly to fertilizing and phytoprotective compositions and even more particularly to phytosanitary and nutritive products for aerial and foliar applications.

[0002] Fertilizers, plant protection products, such as pesticides, nematocides, herbicides, fungicides and other agricultural products are often applied in the form of aqueous solutions or suspensions directly by spraying onto crops. Additives (adjuvants) are often necessary to improve the effects, effectiveness, wettability of these products. Additives are also often used to improve or increase the stability of mixtures containing them.

[0003] Such additives have already been well known and documented in the art for decades, but recent developments tend to favor the use of more effective and environmentally friendly additives. As such, the use of alkoxylated (ethoxylated) alcohols as additives in foliar applications (either for fertilizers or for plant protection products) is now quite common, and several patents, scientific publications and books mention the use of non-ionic surfactants as additives (adjuvants) for agricultural foliar application formulations.

[0004] For reference, V. Fernandez et al (In "Foliar Fertilization, Scientific Principles and Field Practices", IFA, Paris, France, 2013) states on page 38 that the most common hydrophilic polar group in nonionic surfactants is the one based on ethylene oxide, in combination with, among others, fatty alcohol ethoxylates. However, there is no clearly established relationship between the chemistry, hydrophilicity, lipophilicity and phytotoxicity of the compounds.

[0005] The work of J. HAZEN in "Adjuvants: Terminology, Classification and Chemistry", Weed Technology, vol. 14, (2000), 773-784 provides specific definitions of surfactants and wetting agents and mentions the most commonly used chemicals, such as ethoxylated molecules, including nonylphenol-based compounds, fatty amine-based compounds and an iso-tridecanol with 6 moles of ethylene oxide.

[0006] The patent literature contains a great deal of information on wetting agents for agricultural use, among which we can cite patent EP1006792 Bl. This patent discloses formulations of agrochemical concentrates comprising alkoxylated adjuvants, such as C8-C22 alkoxylated alcohols, including C13-C15 alkoxylated alcohols, as well as sorbitan derivatives and even ethoxylated trisiloxanes.

[0007] Patent EP1273230 B1 also deals with wetting agent compositions for agricultural chemicals and discloses agrochemical spreading compositions comprising a surfactant (A) and a surfactant (B) having specific melting points, the surfactant (A) being selected from polyoxyalkylene alkyl ethers, polyoxyalkylene alkylphenyl ethers, polyoxyalkylene polyhydric alcohol fatty acid esters, polyhydric alcohol fatty acid esters, polyoxyalkylene alkylamines, alkylpolyglycosides and glycidyl ethers.

[0008] Document US9456600 B2 describes agricultural chemical spreading agent compositions, containing a polysaccharide, a polyoxyalkylene sorbitan fatty acid ester and at least one nonionic surfactant selected from polyoxyalkylene alkyl ethers, sorbitan fatty acid esters and silicone surfactants. The agricultural chemical spreading agent compositions may also comprise polyhydric alcohol solvents and glycol ether solvents.

[0009] Document US10111420 B2 discloses wetting compositions, for example for the foliage of seeds or plants, comprising a C5-C12 alcohol, and a surfactant such as a branched or linear C6-C15 aliphatic alcohol ethoxylate.

[0010] Document WO2021074547 A1 relates to detergent formulations comprising at least one secondary alcohol alkoxylate, and the use of said secondary alcohol alkoxylate as a surfactant having improved hydrotropic power, i.e. improved solvent solubilization property.

[0011] WO2009155187 A1 relates to cleaning compositions comprising mid-range alkoxylated surfactants or mixtures of alkoxylated surfactants, and their use as triglyceride and crosslinked triglyceride cleaners, formula stabilizers, agents for ultra-concentrated cleaning formulations, pre-wash agents, detergents, agricultural adjuvants, hard surface cleaners and emulsifiers.

[0012] Document WO2012052545 A2 relates to the use of alkoxylated aliphatic alcohols to reduce the viscosity of aqueous agrochemical concentrates.

[0013] Despite all these general teachings on various additives usable in the field of agriculture, there is still a need for specific additives capable of improving the effects, efficiency and wettability of aerial and foliar fertilizer and phytosanitary formulations.

[0014] Water-based solutions of agricultural products, such as pesticides, herbicides, fungicides, nematocides, fertilizers, biostimulants, etc., are commonly applied directly to crop leaves and / or seeds and / or soil. All parts Crops and plants, such as leaves, but also seeds and soils, are generally hydrophobic, meaning that it can be difficult to wet them with water-based solutions. Surfactants can improve this wetting (spreading of droplets on crops, seeds and / or soil) because they reduce the surface tension of the solution, decreasing the contact angle of the droplets on said hydrophobic surfaces.

[0015] A first objective of the present invention is therefore to propose additives which can provide an improvement over known surfactants, in particular over anionic and non-ionic surfactants, in terms of reduction of surface energy and wetting of hydrophobic surfaces, in particular for fertilizing solutions.

[0016] Another objective of the present invention is to provide additives which are effective in terms of reducing surface energy and wetting hydrophobic surfaces, in particular for fertilizer solutions, as well as effective as stabilizers for agricultural compositions, in particular those used.

[0017] Another objective of the present invention is to provide stable and environmentally friendly compositions for agricultural foliar applications, having improved hydrophobic surface wettability.

[0018] Still other objects will be disclosed in the description of the present invention, which is now explained in detail below.

[0019] Therefore, a first object of the invention is the use of at least one compound of formula (I)

[0020] [Chem.l] [RO-(ÀO»-B (1)

[0021] in which: - R is 2-octyl, - AO is a divalent group comprising at least one ethoxy unit (EO) and / or at least one propoxy unit (PO) and / or at least one butoxy unit (BO), - n is zero or a number between 1 and 50, inclusive, and - B is chosen from hydrogen, group B1 and group B2, [Chem. 2] OO H -P—Gq 1B11 — S—OH (82). I " " he ' ' dr o G is -O-[TO]P-R5, where R5 is a group selected from hydrogen, a linear hydrocarbon radical, branched or cyclic C1-C30, [TO] is a divalent group comprising at least one ethoxy unit (EO) and / or at least one propoxy unit (PO) and / or at least one butoxy unit (BO), and p is a number between zero and 100, limits inclusive,

[0022] - J is-O-[T'O]s-R6, - where R6 is a group chosen from hydrogen, a linear, branched or cyclic C1-C30 hydrocarbon radical, [T'O] is a divalent group comprising at least one ethoxy unit (EO) and / or at least one propoxy unit (PO) and / or at least one butoxy unit (BO), and s is a number ranging from zero to 100, inclusive, - m is 1, 2 or 3, - q and r are independently 0, 1 or 2, provided that B is not hydrogen when n is zero,

[0023] provided that m is 1 when B is hydrogen or B2, and

[0024] provided that m + q + r = 3, as a surfactant in agrochemical formulations.

[0025] The surfactants of formula (I) above are compounds known for example from document WO2019092366 when B is hydrogen, from document WO2019092367 when B is B1 and from document WO2019092368 when B is B2. The present invention also encompasses the possible salts of the compounds of formula (I) with organic or mineral bases, in particular when B is B1 or B2. The present invention also encompasses the end-capped surfactant compounds of formula (I) above, such as those described in document WO2021074544.

[0026] According to a preferred embodiment of the present invention, n is 0 or a number between 1 and 30, inclusive, preferably n is 0 or a number between 1 and 25, inclusive, more preferably n is 0 or a number between 1 and 20, inclusive, even more preferably, n is 0 or a number between 1 and 10, inclusive, and in particular n is 0 or a number between 1 and 5, inclusive.

[0027] According to another preferred embodiment, the present invention relates to the use of a surfactant of formula (I) above in which n is zero and B is B1 or B2, and preferably in which n is 0 and B is B1.

[0028] The surfactant of formula (I) for use in the present invention can thus be easily prepared from 2-octanol, which is of particular interest in several respects. Specifically, it is a biodegradable, bio-sourced product and has a good ecotoxicological profile, as well as a reasonable cost.

[0029] Agrochemical formulations comprising at least one 2-octanol-based surfactant of formula (I) above exhibit better efficacy than other C8 alcohol-based surfactant formulations, for example formulations comprising 2-ethylhexyl alkoxylates. 2-Octanol-based surfactants are thus particularly useful, especially in agrochemical formulations, as wetting agents, as spreaders, penetrating agents, activating agents and / or as adjuvants, more particularly for fertilizer solutions, thus improving the effect and effectiveness of fertilizers, as well as other plant protection products.

[0030] As mentioned above, the surfactants of formula (I), for use in the formulations of the present invention, are at least partially bio-sourced, unlike other short (C8-C13) non-ionic surfactants. The 2-octanol-based surfactants for the uses of the present invention are also biodegradable and non-ecotoxic. As a further advantage, such 2-octanol-based surfactants exhibit less negative effects on crops, particularly on leaves.

[0031] According to another preferred embodiment, the present invention involves using a surfactant compound selected from: - 2-octanol + 1 EO, - 2-octanol +1.5 EO, - 2-octanol + 2 EO, - 2-octanol + 2.5 EO, - 2-octanol + 3 EO, - 2-octanol + 3.5 EO, - 2-octanol + 6 EO, - 2-octanol + 6 EO + 4 PO, - 2-octanol + 7 EO, - 2-octanol + 8 EO, - 2-octanol +15 EO, - 2-octanol phosphate ester, - phosphate ester of 2-octanol +3.5 EO, - phosphate ester of 2-octanol +6 EO, - 2-octanol phosphate ester + 7 EO, - phosphate ester of 2-octanol +15 EO, - 2-octanol sulfate, - 2-octanol sulfate +3.5 EO, - 2-octanol sulfate +6 EO, - 2-octanol sulfate + 7 EO, - 2-octanol sulfate +15 EO.

[0032] According to the invention, the claimed use involves at least one surfactant of formula (I) as represented above in an agricultural composition and the total content of surfactant(s) of formula (I) is generally between 0.005% and 5%, preferably between 0.01% and 2%, even more preferably between 0.05% and 1%, by weight, limits included, relative to the total weight of the formulation.

[0033] The surfactant(s) of formula (I) above may also be available in the form of a concentrated formulation, for example between 5% and 95% by weight of at least one surfactant of formula (I) relative to the total weight of the concentrated formulation, said concentrated formulation further comprising one or more solvents chosen from water, glycerol, organic solvents, mineral or vegetable oils and mixtures thereof in all proportions. Such concentrated formulations are advantageously diluted before use, according to practices well known to those skilled in the art.

[0034] The compound of formula (I) described above can thus advantageously be mixed or otherwise used with any type of agricultural formulations well known to those skilled in the art, such as fertilizers, pesticides, nematocides, herbicides, fungicides, coating compositions for granules, fertilizers, seeds and other agricultural products.

[0035] According to another embodiment, the present invention relates to an agricultural formulation comprising at least one surfactant compound of formula (I) as described above, in which the total content of compound(s) of formula (I) is generally between 0.005% and 10%, preferably between 0.01% and 5%, even more preferably between 0.01% and 2% by weight, limits included, relative to the total weight of the formulation.

[0036] Advantageously, such a diluted agricultural formulation further comprises at least one agricultural product chosen from fertilizers, pesticides, nematocides, herbicides, fungicides, coating compositions for granules, fertilizers, seeds and the like, as well as mixtures thereof.

[0037] The formulation of the present invention may also be in the form of a concentrated formulation comprising between 10% and 99.9% by weight of at least one surfactant of formula (I) relative to the total weight of the concentrated formulation.

[0038] Similarly, such a concentrated agricultural formulation advantageously further comprises at least one agricultural product chosen from fertilizers, pesticides, nematocides, herbicides, fungicides, coating compositions for granules, fertilizers, seeds and the like, as well as mixtures thereof.

[0039] The previously described formulations of the present invention may further comprise and advantageously comprise customary additives, solvents and fillers well known and commonly used in the art.

[0040] Among the possible solvents, mention may be made of those chosen from water, organic solvents, mineral or vegetable oils and their mixtures in all proportions, organic solvents possibly comprising alcohols such as glycerol, esters, etc.

[0041] The compound of formula (I) described above, as well as any formulation comprising this or these compounds are particularly suitable for agrochemical formulations, and by "suitable" is meant that the compound of formula (I), and the formulations comprising it, can be mixed or otherwise used with agricultural formulations known to those skilled in the art, such as fertilizers, pesticides, nematocides, herbicides, fungicides, coating compositions for granules, fertilizers, seeds and other agricultural products.

[0042] More particularly, the compound of formula (I), as well as any formulation comprising this or these compounds, are suitable for agrochemical formulations comprising mineral and / or organic fertilizers, nutrients and biological products, such as for example ammonium nitrates, nitrophosphates, ammonium phosphate sulfate, ammonium sulfate, calcium nitrate, diammonium phosphate, potassium chloride, monoammonium phosphate, muriate of potash, potash sulfate, urea, micronutrients, trace elements, biostimulants, bacteria, yeasts, fungi, viruses.

[0043] The formulation of the present invention is more particularly suitable for agrochemical formulations comprising phytosanitary products, such as pesticides, herbicides, fungicides or nematocides, as well as for agrochemical formulations used for coating granules, fertilizers, seeds, etc.

[0044] The formulation according to the invention may also comprise one or more of the following additives, other adjuvants and / or fillers chosen from rheology modifiers, dispersants, anti-sedimentation additives, anti-scaling agents, corrosion inhibitors, pH adjusting agents, antifoams, pigments, coloring matters, antioxidants, preservatives, odoriferous agents, odorants, flavorings, fragrances and spreaders, emulsifiers and surfactants.

[0045] The formulation of the present invention can be prepared according to any method well known to those skilled in the art, and for example, and according to a preferred embodiment of the invention, the surfactant(s) of formula (I) are added to an existing agrochemical formulation which must be improved with regard to its effectiveness and its surface wettability, in particular on the aerial parts of crops, soil or seeds.

[0046] The 2-octanol-based surfactant(s) may be added to the agrochemical formulation at any time, before, during or after the addition of any other component that comprises the final formulation.

[0047] Preferred applications of the compound of formula (I) and corresponding formulations comprising it are spraying, although it may also be applied according to well-known fertigation techniques, drip fertilization and irrigation, directly to the aerial parts of crops, for example to crop leaves, or to the soil, or combinations of two or more of these techniques.

[0048] The agrochemical formulation used in the present invention is also useful for treating all types of substrates requiring such treatment, such as, for example, seeds and / or soils, in the treatment and / or pretreatment of seed coating formulations. The formulation for use in the present invention also finds an interesting application for improving the wetting of soils.

[0049] The agrochemical formulation for use in the present invention is also useful as a soil pretreatment before irrigation or rainfall, as it improves water penetration into hydrophobic soils and / or reduces the amount of water required to achieve good crop yields, the best yields or even the most optimal yields. The amount of irrigation water that can be reduced using the agrochemical formulation used in the present invention can vary widely and, for example, and without limitation, can vary from 1 to 50%, preferably from 2 to 40% and even more preferably from 5 to 30%.

[0050] According to another embodiment, the formulation can also be added to irrigation water in order to obtain similar or identical effects.

[0051] The present invention therefore relates to an agrochemical formulation comprising at least one 2-octanol-based surfactant of formula (I) as described above, as a wetting agent for agricultural product applications.

[0052] The agrochemical formulation comprising the at least one 2-octanol-based surfactant of formula (I) exhibits better performance than other non-ionic surfactants in terms of surface tension reduction and in particular in terms of wetting of hydrophobic surfaces for agrochemical applications.

[0053] As already mentioned, the formulations of the present invention are fully compatible with crop nutrient formulations, in particular crop nutrient formulations well known in the art, and as such are very easy to prepare and can be prepared very economically. In addition, the formulations of the invention are fully or at least partially bio-sourced and biodegradable.

[0054] The following examples are given for illustrative purposes only and are not intended to limit the scope of protection of the present invention, which is defined by the appended claims.

[0055] Example 1: Preparation of compositions according to the invention

[0056] Four different compositions are prepared by simple dilution in water at room temperature with gentle stirring of 10% by weight of potassium chloride (KCl) and 0.1% by weight of four different surfactants, as shown below:

[0057] Surfactant A: 2-octanol + 3.5 EO available from Arkema,

[0058] Surfactant B: 2-octanol + 6 EO + 4 PO available from Arkema,

[0059] Surfactant C: 2-octanol + 7 EO available from Arkema,

[0060] Surfactant D: 2-octanol +15 EO available from Arkema.

[0061] Similarly, other compositions have been prepared with known surfactants, as shown below.

[0062] Example 2: Measurement of surface tension and contact angle on a KC1 solution

[0063] Surface tension measurements are performed by the hanging drop method using a Krüss DSA 30 drop shape analyzer at room temperature. Contact angles of droplets of the same compositions are measured using the same instrument on a hydrophobic surface (Parafilm™) that simulates the hydrophobic surface of plant leaves.

[0064] A characteristic of high-performance agronomic compositions is that they have low surface tension and low contact angle values. These compositions can better distribute the active agricultural component and be absorbed by the crop. They also help to reduce the loss of the composition during their application because the droplet could bounce and get lost during spraying.

[0065] The measured values ​​of surface tension and contact angle with each of the prepared compositions are indicated in Table 1 below: [Tables 1] Composition Surfactant Surface tension (mNm) Contact angle (°) 1 (reference) No additive 70.01 103.29 2 (invention) Surfactant A 24.99 37.63 3 (comparative) Berol 840(1) 26.73 47.96 4 (comparative) Alkoxylated C10 OXO fatty alcohol 3EO / 4OP / 2EO, available from Arkema 27.99 50.26 5 (comparative) Sorbitan trioleate 20 EO, available from Arkema 37.92 59.63 6 (comparative) Alkoxylated C12-C14 fatty alcohol 5EO / 4OP, available from Arkema 29.21 53.65 7 (comparative) Alkoxylated C16-C18 alcohol ethoxylates, available at Arkema 40.53 80.38 8 (comparative) Tristyrylphenol ethoxylate 3,3 EO, available at Arkema 41.5 95.03 (1) 2-ethylhexyl-4 EO, available from Nouryon

[0066] A significant decrease in surface tension and contact angle can be observed with composition 2 according to the invention, compared to reference composition 1 (without surfactant). It should also be noted that lower surface tension and contact angle values ​​are obtained with composition 2 according to the invention, compared to other non-ionic surfactants having a hydrocarbon chain (alkyl) of greater mass or different structure. This clearly demonstrates the interest of 2-octanol-based surfactants for use in the agrochemical compositions of the present invention compared to other non-ionic surfactants, in aqueous solutions of KC1.

[0067] Example 3: Surface tension and contact angle on a MAP solution

[0068] Other compositions are prepared by adding 10% by weight of monoammonium phosphate and 0.1% by weight of various surfactants, as indicated below, by simple dilution in water and at room temperature with gentle stirring. Surface tension measurements are carried out by the hanging drop method using a Krüss DSA 30 drop shape analyzer at room temperature. Droplet contact angles of the same compositions are measured using the same instrument on a hydrophobic surface (Parafilm™) which simulates the hydrophobic surface of plant leaves. The values ​​measured from these compositions are shown in Table 2 below: [Tables2] Composition Surfactant Surface tension (mNm) Contact angle (°) 9 (reference) No additive 69.93 103.54 10 (invention) Surfactant A 26.12 33.81 11 (invention) Surfactant E(2) 23.77 34.93 12 (comparative) Berol 840 25.44 42.08 13 (comparative) Alkoxylated C10 OXO fatty alcohol 3EO / 4OP / 2EO, available from Arkema 27.83 50.92 14 (comparative) Alkoxylated C12-C14 fatty alcohol 5EO / 4OP, available from Arkema 27.6 55.88 (2) 2-octanol phosphate ester, available from Arkema

[0069] In this example, a significant reduction in surface tension and contact angle can be observed by composition 10 (invention) compared to reference composition 9 as before. As shown, lower surface tension and contact angle values ​​were obtained with compositions 10 and 11 (invention) compared to other non-ionic surfactants, having a hydrocarbon, alkyl, larger mass or different structure section. In this case, however, the surface tension values ​​are closer between the different compositions. Nevertheless, a clear advantage of the two compositions of the invention (10 and 11) was obtained in terms of contact angle compared to the rest of the comparison compositions.As in the previous example, the wetting agent on composition 12, which also has 8 carbon atoms in its hydrophobic chain as in that used in composition 10 (invention), has larger contact angle values ​​than that used in the subject of the invention. This example further demonstrates the interest of 2-octanol-based surfactants in agrochemical compositions compared to other non-ionic surfactants.

[0070] Example 4: Surface tension and contact angle on an NPK 19-19-19

[0071] The compositions are prepared by adding 10% by weight of a soluble NPK fertilizer 19-19-19 and 0.1% by weight of a surfactant by simple dilution in water and at room temperature with gentle stirring. Surface tension measurements are carried out by the hanging drop method using a Krüss DSA 30 drop shape analyzer at room temperature. The contact angles of droplets of the same compositions are measured using the same instrument on a hydrophobic surface (Parafilm TM) which simulates the hydrophobic surface of plant leaves. The values ​​obtained from different compositions, including other non-ionic surfactants, are shown in the table below: [Tables3] Composition Surfactant Surface tension (mNm) Contact angle (°) 15 (reference) No additive 68.11 95.48 16 (invention) Surfactant A 26.54 41.56

[0072] This example shows that composition 16 according to the invention also significantly reduces the surface tension and contact angle of complex soluble fertilizers, such as those comprising a mixture of several chemical species such as ammonium sulfates, urea, monoammonium phosphates and potassium nitrate, among others.

[0073] Example 5: Surface tension and contact angle on a KNO3 solution

[0074] Still other compositions are prepared by adding 10% by weight of nitrate of potassium (KNO3) and 0.1% by weight of surfactant by simple dilution in water and at room temperature with gentle stirring. Surface tension measurements are carried out by the hanging drop method using a Krüss DSA 30 drop shape analyzer at room temperature. The contact angles of droplets of the same compositions are measured using the same instrument on a hydrophobic surface (Parafilm™) which simulates the hydrophobic surface of plant leaves. The values ​​obtained from different compositions, including other non-ionic surfactants, are shown in Table 4 below: [Tables 4] Composition Surfactant Surface tension (mNm) Contact angle (°) 17 (reference) No additive 68.11 95.48 18 (invention) Surfactant A 29.96 50.91 19 (invention) Surfactant B 31.95 65.77 20 (invention) Surfactant C 36.05 69.24 21 (invention) Surfactant D 46.07 89.11

[0075] In this example, a significant reduction in surface tension and contact angle can be observed by the compositions of the present invention (18 to 21) compared to the reference composition 17. A difference in performance is also observed with the increase in the number of oxyethylene groups. The best performance is observed with composition 18 which contains 2-octanol containing the smallest number of ethoxy groups (3).

[0076] Example 6: Surface tension / contact angle on a KC1 solution effect of EO comparison

[0077] Compositions 22-25 are prepared by adding 10% by weight of potassium chloride and 0.1% by weight of surfactant by simple dilution in water and at room temperature with gentle stirring. Surface tension measurements are carried out by the hanging drop method using a Krüss DSA 30 drop shape analyzer at room temperature. The contact angles of droplets of the same compositions are measured using the same instrument on a hydrophobic surface (Parafilm™) which simulates the hydrophobic surface of plant leaves. A comparison is made between 2-octanol-based surfactants of formula (I) and other ethoxylated 2-ethylhexyl chain surfactants. The values ​​obtained from the different compositions are shown in Table 5 below: [Tables 5] Composition Surfactant Surface tension (mNm) Contact angle (°) 1 (reference) No additive 70.01 103.29 2 (invention) Surfactant A 24.99 37.63 3 (comparative) Berol 840 26.73 47.96 22 (invention) Surfactant C 33.17 60.08 23 (comparative) 2-ethylhexyl alkoxylate, 7EO® 38.47 77.65 24 (invention) Surfactant D 42.18 88.49 25 (comparative) 2-ethylhexyl alkoxylate, 15EO(4) 43.44 90.29 (3) prepared on a laboratory scale according to known methods, from 2-ethylhexanol with ethylene oxide under basic conditions (KOH).

[0078] (4) prepared on a laboratory scale according to known methods, from 2-ethylhexanol with ethylene oxide under basic conditions (KOH).

[0079] In this example, a decrease in surface tension and contact angle is observed with composition 2 (according to the invention) compared to composition 3 (comparison), with composition 22 (according to the invention) compared to composition 23 (comparison) and with composition 24 (according to the invention) compared to composition 25 (comparison). Each pair of compositions compared has the same number of ethylene oxide units in their structure. This example shows the advantage of 2-octanol-based wetting agents of formula (I) compared to 2-ethylhexyl-based surfactants in terms of surface tension reduction and wetting, even though all surfactants are based on alcohols having 8 carbon atoms.

Claims

Claims

1. Use of at least one compound of formula (I) [Chem. 3] [RO-CAO^-B (Q in which: - R is 2-octyl, - AO is a divalent group comprising at least one ethoxy unit (EO) and / or at least one propoxy unit (PO) and / or at least one butoxy unit (BO), - n is 0 or a number between 1 and 50, inclusive, and - B is chosen from hydrogen, group B1 and group B2, [Chem. 4] OH ï H -P—Gq (BU. —S-OH ®2), ( n ' - G is -O-[TO]p-R5, where R5 is a group selected from hydrogen, a linear, branched or cyclic CrC3o hydrocarbon radical, [TO] is a divalent group comprising at least one ethoxy unit (EO) and / or at least one propoxy unit (PO) and / or at least one butoxy unit (BO), and p is a number between 0 and 100, inclusive, - J is -O-[T'O]s-R6, - where R6 is a group chosen from hydrogen, a linear, branched or cyclic C1-C30 hydrocarbon radical, [T'O] is a divalent group comprising at least one ethoxy unit (EO) and / or at least one propoxy unit (PO) and / or at least one butoxy unit (BO), and s is a number between 0 and 100, limits included, - m is 1, 2 or 3, - q and r are independently 0, 1 or 2, provided that B is not hydrogen when n is zero, provided that m is 1 when B is hydrogen or B2, and provided that m + q + r = 3, as a surfactant in agrochemical formulations.

2. Use according to claim 1, of a compound of formula (I), wherein formula (I) includes salts of compounds of formula (I) with organic or inorganic bases, as well as end-capped compounds of formula (I).

3. Use according to claim 1, wherein n is 0 or a number from 1 to 30, inclusive, preferably n is 0 or a number from 1 to 25, inclusive, more preferably n is 0 or a number from 1 to 20, inclusive, even more preferably, n is 0 or a number between 1 and 10, inclusive, and in particular n is 0 or a number between 1 and 5, inclusive.

4. Use according to claim 1, wherein n is equal to 0 and B is B1 or B2, and preferably wherein n is equal to 0 and B is B1.

5. The use of claim 1, wherein the surfactant compound of formula (I) is selected from: - 2-octanol + 1 EO, - 2-octanol +1.5 EO, - 2-octanol + 2 EO, - 2-octanol + 2.5, - EO, - 2-EO, - + 3 2-octanol + 3.5 EO, - 2-octanol + 6 EO, - 2-octanol + 6 EO + 4 PO, - 2-octanol + 7 EO, - 2-octanol + 8 EO, - 2-octanol +15 EO, - phosphate ester of 2-octanol, - phosphate ester of 2-octanol +3.5 EO, - 2-octanol phosphate ester +6 EO, - 2-octanol phosphate ester + 7 EO, - 2-octanol phosphate ester +15 EO, - 2-octanol sulfate, - 2-octanol sulfate +3.5 - 2-octanol sulphate + - 2-octanol sulfate + 7 EO, - 2-octanol sulfate +15 EO.

6. Formulation comprising at least one surfactant compound of formula (I) according to any one of claims 1 to 5, in which the total content of compound(s) of formula (I) is between 0.005% and 10%, preferably between 0.01% and 5%, even more preferably between 0.01% and 2%, by weight, limits included, relative to the total weight of the formulation.

7. Formulation according to claim 6, further comprising at least one agricultural product selected from fertilizers, pesticides, nematocides, herbicides, fungicides, coating compositions for granules, fertilizers, seeds and the like as well as mixtures thereof.

8. Formulation comprising at least one surfactant compound of formula (I) according to any one of claims 1 to 5, comprising between 10% and 99.9% of at least one surfactant of formula (I), by weight relative to the total weight of the concentrated formulation.

9. Formulation according to claim 8, further comprising at least one agricultural product selected from fertilizers, pesticides, nematocides, herbicides, fungicides, coating compositions for granules, fertilizers, seeds and the like as well as mixtures thereof.

10. A formulation according to claim 6 or 7, further comprising additives, solvents and fillers selected from rheology modifiers, dispersants, anti-settling additives, anti-scaling agents, corrosion inhibitors, pH adjusting agents, antifoams, pigments, colorants, antioxidants, preservatives, odoriferous agents, odorants, flavorings, fragrances and spreaders, emulsifiers and surfactants.

11. Use of a compound of formula (I) according to any one of claims 1 to 5 or of a formulation according to any one of claims 6 to 8, for spraying, drip fertilizing or irrigating, directly on the aerial parts of crops, on the leaves of crops, on the soil, on seeds, or combinations of two or more of these techniques.

12. An agrochemical formulation comprising at least one 2-octanol-based surfactant of formula (I) according to any one of claims 1 to 5, as a wetting agent for agricultural product applications.

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