Bio-based compounds

Abstract

The invention relates to a ketal-amide derivative of levulinic acid.

Description

Technical Field

[0001] The present invention relates to biobased compounds which are suitable as biodegradable and eco-friendly solvents, especially in agrochemicals. Background Art

[0002] Many chemical compounds are used industrially as solvents, for example for the preparation of chemicals and materials, for the formulation of chemical compounds, or for the treatment of surfaces. For example, solvents are used for the formulation of agrochemical compounds, especially phytosanitary active agents (fertilizers, pesticides...), which are, for example, in the form of emulsifiable concentrates (ECs) intended to be diluted in water by farmers before application to the fields.

[0003] In the case of fertilizers as active agents, nitrogen stabilizers (such as urease inhibitors or nitrification inhibitors) are usually applied to the soil or on the soil together with the fertilizer as efficiency-enhanced fertilizers (EEFs). This ensures that the stabilizer comes into contact with the soil together with the fertilizer. The nitrogen stabilizer is dissolved in a polar solvent and can be incorporated into the fertilizer by adding this solution to the melt before granulating or pelletizing the fertilizer. For example, such a method for urease inhibitors is described in U.S. Patent No. 5,352,265. Another option is to apply a fertilizer stabilizer (such as a urease inhibitor) as a coating to the granules or pellets. In these methods, solvents such as DMSO (dimethyl sulfoxide), NMP (N-methyl-2-pyrrolidone), DMF (N,N-dimethylformamide), DMAc (N,N-dimethylacetamide) or diol-based solvents are used. However, these solvents are harmful to the environment, have poor biodegradability characteristics, are very mobile in the environment (because they are highly water-soluble), and are potentially toxic to humans or small organisms.

[0004] The industry in the agricultural field tries to achieve the highest possible concentration of one or more agroactive compounds in the corresponding formulations, because a high concentration of one or more agrochemical compounds allows for a reduction in the volume to be applied and thus savings in terms of the adjuvant materials applied as well as in terms of packaging and logistics. Therefore, in principle, highly concentrated stable formulations and co-formulations with environmentally friendly adjuvants are of interest.

[0005] For agroactive compounds with low or relatively low water solubility, the use of suitable solvents for the preparation of concentrated liquid formulations is of particular interest, which are in the form of emulsifiable concentrates (ECs), concentrated emulsions in water (EWs), microemulsions (MEs), suspoemulsions (SEs), oil dispersions (ODs), dispersible concentrates (DCs).

[0006] Such concentrated formulations of agrochemical compounds are usually diluted before agricultural use. The dilution by farmers is usually carried out by mixing the agrochemical formulation with water.

[0007] In addition, certain solid agroactive compounds are often difficult to formulate. For certain agrochemical compounds, it is difficult to produce concentrated formulations that are easy for farmers to dilute, stable and have no substantial drawbacks (actual or perceived drawbacks) in terms of safety, toxicity and / or ecotoxicity. For certain agrochemical compounds, it is difficult to formulate at a relatively high concentration with sufficient stability. In particular, it is necessary to avoid the appearance of crystals, especially at low temperatures and / or during dilution and / or during storage of the composition, especially when stored at low temperatures. Crystals can have harmful effects, especially blocking the filters of devices for spreading the diluted composition, blocking spraying devices, reducing the overall activity of the formulation, creating unnecessary problems in waste management procedures for removing crystals, and / or causing poor distribution of one or more agro-materials on farmland.

[0008] More generally, the industry is looking for novel compounds that enable the modification or optimization of products and methods in which solvents, especially polar solvents, are used. In particular, the agrochemical industry is constantly looking for new solvents and solvent compositions that have satisfactory properties for agricultural applications (such as good dissolution efficiency). In addition, the cost of solvent compositions should generally be moderate, and preferably they should have favorable toxicological and / or ecotoxicological characteristics, especially low toxicity and / or low hazard potential, and / or low volatility (low VOC - volatile organic compounds) and / or advantageously a high degree of biodegradability and / or renewability.

[0009] Accordingly, an object of the present invention is to provide a preferably bio-based solvent that is advantageously non-toxic, environmentally safe to use (preferably having good biodegradability characteristics) and particularly suitable for all of the above applications, especially for dissolving polar agrochemical compounds such as biocides and fertilizer stabilizers.

[0010] There is a limited number of eco-friendly polar solvents on the market, such as (dihydrolevoglucosenone), PolarClean, NBP (N-butyl-2-pyrrolidone), N,N-dimethyl lactamide and ADMA 10. However, these solvents are not always suitable for all purposes, including dissolving high concentrations of polar agroactive compounds such as fertilizer stabilizers, while generally also ensuring storage stability over different temperature ranges.

[0011] In addition, while the use of a specific solvent system based on a single solvent (such as N-methyl-2-pyrrolidone (NMP)) can enable a certain number of agro-materials to be dissolved, it is considered to present a reproductive toxicity hazard, especially for operators and users handling it.

[0012] Likewise, in other application areas, such as polymer conversion or recycling, and household and personal care, ecologically friendly multi-purpose solvents are needed.

[0013] Accordingly, it is an object of the present invention to provide a preferably sustainable, bio-based and ecologically friendly solvent which can advantageously dissolve high concentrations of polar compounds (such as biocides and fertilizer stabilizers), while generally also ensuring storage stability within different temperature ranges. Summary of the Invention

[0014] These objects have been unexpectedly solved by a compound having the formula (I):

[0015]

[0016] wherein

[0017] R 1 and R 2 are independently selected from -(C1-C6) alkyl, including -(C1) alkyl, -(C2) alkyl, -(C3) alkyl, -(C4) alkyl, -(C5) alkyl, and -(C6) alkyl, which may optionally be interrupted and / or substituted by a heteroatom or a heteroatom-containing group, or R 1 and R 2 form a heterocyclic ring containing 4 to 8 atoms with the nitrogen atom; and

[0018] R 3 is hydrogen, or -(C1-C4) alkyl, which may optionally be interrupted and / or substituted by a heteroatom or a heteroatom-containing group;

[0019] provided that when R 1 and R 2 are -CH3, then R 3 is not hydrogen.

[0020] A compound having the formula (I) wherein R 1 and R 2 are -CH3 and R 3Hydrogen) has been described as a starting material for the production of molecules of interest in the field of pharmaceutical chemistry (such as tetracyclines): "Synthesis of phenols by polyketide condensation and an efficient synthesis of 3,5-dioxoalkanoates from amides [Synthesis of phenols by polyketide condensation and an efficient synthesis of 3,5-dioxoalkanoates from amides]", Yamaguchi et al., Chemistry Letters (1985), (8), 1145-8. In this paper, no details on the properties (physical properties, analytical data...) of this compound were given, nor were details on its synthesis.

[0021] The ketal-amide derivatives of levulinic acid according to the invention, i.e., the compounds having formula (I) as defined above, are biobased compounds which can be produced from levulinic acid, diol and secondary amine structural units following sustainable chemical processes (i.e., advantageously showing very good atom economy and generating little waste), and these levulinic acid, diol and secondary amine structural units can preferably all be obtained by biological methods or from biobased raw materials.

[0022] It has been found that the compounds having formula (I) are advantageously eco-friendly solvents, preferably having good safety and sustainable ecotoxicity characteristics (where there is no hazard classification or very little hazard classification and no ecotoxicity or very low ecotoxicity), and moreover are excellent solvents. It has been found that the compounds of the present invention are excellent solvents for dissolving the following: biocides, such as fungicides, herbicides and insecticides, and / or (nitrogen) fertilizer stabilizers (such as urease inhibitors and nitrification inhibitors), as well as many other polar compounds. It has also been found that the compounds of the present invention can also be used as solvents in many other applications such as coating applications, for manufacturing membranes, for manufacturing solid batteries, for the recycling of polymers, for cleaning equipment, and for household and personal care compositions. These compounds are preferably biodegradable.

[0023] The present invention further relates to a method for producing the compounds of the present invention from levulinic acid or its esters or salts, the method comprising at least the following steps in any order:

[0024] (a) ketalization with a compound having the formula R 3 -CH(OH)CH2OH

[0025] (b) amidation with an amine having the formula HNR 1 R 2

[0026] wherein R 1 , R 2 and R 3 are as defined above.

[0027] In one aspect, the present invention relates to a composition comprising a compound of the present invention.

[0028] In another aspect, the present invention relates to the use of a compound of the present invention as a solvent (especially in agricultural formulations for plant protection products such as pesticides), for biostimulants, biopreparations, plant growth regulators, and in efficiency-enhanced fertilizer formulations containing urease inhibitors or nitrification inhibitors. Detailed Embodiments

[0029] The following definitions are relevant to the embodiments of the present invention.

[0030] The meaning of the term "comprising" should be construed as covering all specifically mentioned features as well as optional, additional, unspecified features, while the term "consisting of" includes only those features as specified. Thus, "comprising" includes, as a limiting case, the compositions specified by "consisting of".

[0031] Unless otherwise stated, the term "wt.%" refers to the amount of the corresponding component by weight based on the total amount of the composition.

[0032] Unless the context clearly indicates otherwise, as used herein, the singular forms "a / an" and "the" include both singular and plural referents. For example, "a pesticide" means one pesticide or more than one pesticide.

[0033] As used herein, the term "(C x -C y"Alkyl" in each case represents a straight-chain or branched-chain alkyl group having from x to y carbon atoms. Examples of (C1-C6) alkyl are methyl, ethyl, n-propyl, isopropyl, n-butyl, 2-butyl, isobutyl, tert-butyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, and 1-ethyl-2-methylpropyl.

[0034] As used herein, the term "alkoxy" in each case represents a straight-chain or branched-chain alkyl group bonded via oxygen, and thus alkoxy can be represented as -O-alkyl. Examples of alkoxy are methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, 2-butoxy, isobutoxy, and tert-butoxy.

[0035] As used herein, the term "alkoxyalkyl" can be represented as -alkyl-O-alkyl and refers to an alkyl group typically containing from 1 to 4, preferably 1 to 2 carbon atoms, where 1 carbon atom carries an alkoxy group typically containing from 1 to 4, preferably 1 or 2 carbon atoms as defined above. Examples are -CH2OCH3, -CH2-O-C2H5, 2-(methoxy)ethyl, and 2-(ethoxy)ethyl.

[0036] The term "alkyl group substituted with a heteroatom" refers to an alkyl group in which one or more of the hydrogen atoms are substituted with a heteroatom. Non-limiting examples of heteroatoms are F, Cl, O, and N. This definition includes cases where the heteroatom forms a multiple bond (double bond or triple bond) with a C atom. The term "alkyl group substituted with a heteroatom-containing group" refers to an alkyl group in which one or more of the hydrogen atoms are substituted with a heteroatom-containing group.

[0037] The term "heteroatom-containing group" refers to a hydrocarbon molecule or molecular fragment in which one or more carbon and / or hydrogen atoms are replaced with a heteroatom, typically O or N. This definition includes cases where the heteroatom forms a multiple bond (double bond or triple bond) with a C atom.

[0038] The term "alkyl interrupted by a heteroatom" refers to an alkyl group in which a heteroatom is inserted between carbon-carbon bonds. For example, in the case where the heteroatom is oxygen, the alkyl interrupted by a heteroatom can also be referred to as an alkoxyalkyl. The term "alkyl interrupted by a heteroatom-containing group" refers to an alkyl group in which a heteroatom-containing group is inserted between carbon-carbon bonds. The term "heteroatom-containing group" has the same meaning as above.

[0039] Non-limiting examples of the term "heterocyclic ring containing 4 to 8 atoms" include pyrrolidine, piperidine, piperazine, and morpholine.

[0040] Non-limiting examples of the term "pesticide" (which includes biopesticides) include fungicides, herbicides, insecticides, acaricides, algicides, molluscicides, miticides, nematicides, biocides, and rodenticides. Specific examples of pesticides can be found in the book "The Pesticide Manual", 18th Edition, British Crop Protection Council 2018.

[0041] As used herein, the term "nitrogen fertilizer stabilizer" refers to a reagent that prevents or slows down the biodegradation kinetics of fertilizers. Non-limiting examples are urease inhibitors or nitrification inhibitors such as NBPT (N-(n-butyl)thiophosphoric triamide), DCD (dicyandiamide), and NPPT (N-(n-propyl)thiophosphoric triamide). Nitrification inhibitors delay the bacterial oxidation of ammonium ions in fertilizers by inhibiting the activity of bacteria of the genus Nitrosomonas in the soil, which converts ammonium to nitrite. Urease inhibitors inhibit the conversion of urea to ammonia and CO2. Fertilizers containing fertilizer stabilizers are commonly referred to as slow-release or controlled-release fertilizers or efficiency-enhanced fertilizers (EEF). Non-limiting examples of nitrification inhibitors include DCD, DMPP (3,4-dimethylpyrazole phosphate), nitrapyrin (2-chloro-6-(trichloromethyl)pyridine), TU (thiourea), MT (1-mercapto-1,2,4-triazole), AM (2-amino-4-chloro-6-methylpyrimidine), ASU (1-amide-2-thiourea), HPLC (1H-1,2,4-triazole), 3,4-dimethylpyrazole succinic acid (DMPSA). Non-limiting examples of urease inhibitors include NBPT, NPPT, and CNPT (cyclohexylphosphoric triamide).

[0042] As used herein, the term "composition" refers to a mixture comprising at least the compound of the present invention and another ingredient / compound. This mixture can be homogeneous (i.e., a solution) or heterogeneous (i.e., a dispersion, emulsion, suspension, suspoemulsion).

[0043] As used herein, the term "room temperature" refers to a temperature of from 20°C to 30°C, typically a temperature of 25°C.

[0044] The terms "(a)", "(b)", "(c)", etc. in the specification and claims are used to distinguish features and are not necessarily used to describe an order or temporal order.

[0045] Preferred embodiments according to the present invention are defined below. The preferred embodiments are preferred individually or in combination. Further, it should be understood that the following preferred embodiments refer to all aspects of the present invention, namely compounds, methods, compositions, and uses of the compounds.

[0046] In an embodiment, the present invention relates to a compound having the formula (I):

[0047]

[0048] wherein

[0049] R 1 and R 2 are independently selected from -(C1-C6)alkyl, including -(C1)alkyl, -(C2)alkyl, -(C3)alkyl, -(C4)alkyl, -(C5)alkyl, and -(C6)alkyl, which may optionally be interrupted and / or substituted by a heteroatom or a heteroatom-containing group, or R 1 and R 2 form a heterocyclic ring containing 4 to 8 atoms with the nitrogen atom; and

[0050] R 3 is hydrogen, or -(C1-C4)alkyl, which may optionally be interrupted and / or substituted by a heteroatom or a heteroatom-containing group;

[0051] provided that when R 1 and R 2 are -CH3, then R 3 is not hydrogen.

[0052] In an embodiment, R 1 and R 2 are independently selected from -(C1-C3)alkyl, including -(C1)alkyl, -(C2)alkyl, and -(C3)alkyl. Preferably, R 1 and R 2 are independently selected from methyl and ethyl, or form a pyrrolidine, piperidine or morpholine heterocyclic ring with the nitrogen atom. Particularly preferably, R 1 and R 2 are both -CH3.

[0053] In an embodiment, R 3is a -(C1-C2)alkyl group, optionally interrupted and / or substituted by a heteroatom, where the heteroatom is preferably oxygen. In an embodiment, R 3 is hydrogen.

[0054] In a specific embodiment, notably when R 1 and R 2 are independently selected from -(C1-C3)alkyl groups (including -(C1)alkyl, -(C2)alkyl, and -(C3)alkyl), for example when R 1 and R 2 are independently selected from methyl and ethyl, R 3 is a -(C1-C2)alkyl group, that is, R 3 is -(C1)alkyl or -(C2)alkyl, preferably R 3 is -CH3.

[0055] In a preferred embodiment, R 3 is -(C1)alkyl (that is, R 3 is -CH3) or hydroxymethyl (that is, R 3 is -CH2-OH).

[0056] And thus, in a particularly preferred embodiment, the compound having formula (I) is 3-(2,4-dimethyl-1,3-dioxolan-2-yl)-N,N-dimethylpropanamide (that is, R 1 , R 2 and R 3 are each -CH3) or 3-(4-(hydroxymethyl)-2-methyl-1,3-dioxolan-2-yl)-N,N-dimethylpropanamide (that is, R 1 and R 2 are both -CH3 and R 3 is -CH2-OH). Very preferably, the compound having formula (I) is 3-(2,4-dimethyl-1,3-dioxolan-2-yl)-N,N-dimethylpropanamide (that is, R 1 , R 2 and R 3 are each -CH3).

[0057] Advantageously, the compound having formula (I) has good to excellent dissolution properties, is preferably biodegradable and preferably has very good safety and sustainable ecotoxicity characteristics, where there is no hazard classification or very low hazard classification and no ecotoxicity or very low ecotoxicity.

[0058] Preferably, the compound having formula (I) has a renewable carbon index (RCI) of at least 0.80, particularly in the range of 0.80 to 1.

[0059] Renewable carbon generally requires avoiding or substituting all carbon sources that use any additional fossil carbon from the geosphere. Renewable carbon can come from the biosphere, the atmosphere, or the technosphere, but not from the geosphere.

[0060] Renewable carbon is herein defined as carbon derived from recently living plant or animal organisms (as opposed to carbon derived from fossil carbon based on coal, oil, or petroleum), and carbon derived from CO2 capture.

[0061] The Renewable Carbon Index (RCI) is defined as the value calculated by dividing the number of renewable carbons by the total number of carbons in the entire molecule. For example, if 80% of the number of carbons present are renewable carbons, then the RCI is 0.8.

[0062] In an embodiment, the present invention relates to a method for producing the compounds of the present invention from levulinic acid or its esters or salts, the method comprising at least the following steps in any order:

[0063] (a) ketalization with a compound having the formula R 3 -CH(OH)-CH2OH

[0064] (b) amidation with an amine having the formula HNR 1 R 2 wherein R

[0065] to R 1 to R 3 are as defined above.

[0066] The ketalization in step (a) is preferably acid-catalyzed and an equilibrium reaction that produces water as a by-product. Thus, the ketalization is preferably assisted by removing water during the reaction, for example, by distillation (such as vacuum distillation or using a so-called Dean-Stark apparatus, azeotropic distillation using a suitable solvent that forms an azeotrope with water such as toluene, xylene,...) to drive the equilibrium of the reaction towards completion. After the reaction, step a) preferably further includes neutralization and removal of the acid catalyst.

[0067] In an embodiment, step (b) is base-catalyzed, especially when starting from levulinate. In this case, an alcohol is produced as a by-product. Preferably, step (b) further comprises neutralizing the base catalyst and removing the salt by-products after the reaction. The base can be preferably neutralized, for example, with an ion exchange resin (such as Amberlite ion exchange resin), which has the advantage of avoiding cumbersome removal of salt by-products (compared to mineral acids), since the resin can be easily filtered off. Preferably, when neutralizing the base catalyst with an aqueous solution of an acid, the pH of the solution is controlled to avoid hydrolysis of the ketal under acidic conditions. When starting from levulinic acid, the amidation in step b) does not require any catalyst and can be carried out thermally at a temperature in the range of 120 °C - 250 °C in the presence of water removal. In this case, an intermediate ammonium carboxylate salt is initially formed, which is dehydrated by heating to the amide.

[0068] In a preferred embodiment, the production method starts from a bio-based levulinic acid or its ester derivative (such as methyl levulinate). The reaction scheme is depicted below, where R 0 is hydrogen or an alkyl group, preferably methyl or ethyl.

[0069]

[0070] In a preferred embodiment, step (a) is carried out first, followed by step (b). These two steps can include additional purification steps by methods known in the art, such as (vacuum) distillation, filtration, liquid-liquid extraction, crystallization or column chromatography.

[0071] Other methods for producing the compounds of the present invention can also be used. For example, instead of starting from levulinic acid or its ester or salt, one can start directly from a ketal-ester intermediate (such as those obtained in step (a)) and only carry out step (b) of the above method. As a non-limiting example, 3-(4-(hydroxymethyl)-2-methyl-1,3-dioxolan-2-yl)-N,N-dimethylpropanamide can be obtained by step (b) from ethyl glycerol-ketal levulinate, which is prepared by following the protocol described in Example 6 of WO 2012 / 018939 using methanesulfonic acid instead of 2-naphthalenesulfonic acid as the catalyst. And, vice versa: one can start directly from an amine intermediate (such as those obtained in step (b)) and only carry out step (a) of the above method.

[0072] In an embodiment, the present invention relates to a composition comprising a compound of the present invention or a mixture of compounds of the present invention. This composition can be at least a part of a formulation intended for a specific function, such as a phytosanitary (or agricultural) formulation, a cleaning formulation, a stripping formulation, a degreasing formulation, a lubricant or textile formulation, a coating formulation such as a painting formulation or a pigment or ink formulation.

[0073] In a very advantageous embodiment, the composition according to the present invention is a phytosanitary (or agricultural) formulation, preferably a concentrated phytosanitary (or agricultural) formulation, i.e., a formulation containing a phytosanitary (agricultural) active compound. Many active substances are used in agriculture, such as fertilizers, biostimulants, plant growth regulators, natural plant defense enhancers, inoculants or pest control agents (e.g., herbicides, insecticides, acaricides, fungicides, algicides, molluscicides, miticides, nematicides, biocides or rodenticides such as rat poison).

[0074] This phytosanitary (or agricultural) formulation can contain:

[0075] a) A phytosanitary (agricultural) active compound;

[0076] b) A compound of the present invention, usually as a solvent;

[0077] c) Optionally at least one emulsifier, preferably a surfactant; and

[0078] d) Optionally water.

[0079] As used herein, the term "phytosanitary active compound" or "agricultural active compound" means an active ingredient particularly used in agricultural practices (including cultivating the soil for crop growth). However, the use of agricultural (phytosanitary) active compounds is not limited to application to crops. Agricultural active compounds (or materials) can be applied to any surface, for example for cleaning or for helping or inhibiting the growth of living organisms. Other non-crop applications include, but are not limited to, application to turf and ornamental plants, and application to railway weeds.

[0080] Agricultural (phytosanitary) active compounds are usually products in pure or highly concentrated form.

[0081] Agricultural (or phytosanitary) active compounds are preferably selected from pest control agents (including biopesticides), fertilizers, fertilizer stabilizers, nutrients, biostimulants, plant growth regulators, natural plant defense enhancers, inoculants and mixtures thereof.

[0082] Advantageously, the phytosanitary (or agricultural) formulation according to the present invention contains at least one pest control agent.

[0083] For example, the at least one pesticidal agent can be selected from fungicides, herbicides, insecticides, acaricides, algicides, molluscicides, miticides, nematicides, biocides, and rodenticides (e.g., rodent poisons).

[0084] Non-limiting examples of fungicides suitable for use in the agricultural (or phytosanitary) formulations of the present invention include azoles such as prothioconazole, epoxiconazole, difenoconazole, propiconazole, cyproconazole, tebuconazole; strobilurins such as azoxystrobin, trifloxystrobin, picoxystrobin, fluoxastrobin, pyraclostrobin; and SDHIs (carboxamides) such as bixafen, fluxapyroxad, benzovindiflupyr, fluopyram; and mixtures thereof.

[0085] The agro(phytosanitary) active compound can be water-insoluble at 20 °C and atmospheric pressure (i.e., 1.013 x 10 5 Pa).

[0086] In particular, the agro(phytosanitary) active compound can be soluble in water at 20 °C and atmospheric pressure (i.e., 1.013 x 10 5 Pa) up to no more than 100 g / L, usually no more than 20 g / L, notably no more than 5 g / L, for example no more than 1 g / L and even no more than 0.2 g / L.

[0087] In another embodiment, the compound or composition of the present invention forms part of a fertilizer formulation, preferably an efficiency-enhanced fertilizer formulation, which contains fertilizers and / or fertilizer stabilizers, in particular nitrogen fertilizers and / or nitrogen fertilizer stabilizers and / or urease inhibitors and / or nitrification inhibitors.

[0088] The fertilizers and / or fertilizer stabilizers, in particular nitrogen fertilizers and / or nitrogen fertilizer stabilizers and / or urease inhibitors and / or nitrification inhibitors can be N-(n-butyl) thiophosphoric triamide (NBPT) and / or dicyandiamide (DCD).

[0089] In another embodiment, the fertilizer formulation further contains at least one biostimulant, a plant growth regulator, a natural plant defense enhancer, and / or an inoculant.

[0090] In another embodiment, the fertilizer formulation further contains at least one pesticidal agent, such as a fungicide, herbicide, insecticide, acaricide, algicide, molluscicide, miticide, nematicide, biocide, or rodenticide (e.g., rodent poison).

[0091] Generally, the amount of one or more phytosanitary (agrochemical) active compounds in the phytosanitary (agro) formulation according to the invention ranges from 0.01% to 90% by weight, preferably from 0.1% to 90% by weight, more preferably from 0.1% to 80% by weight; even more preferably from 0.5% to 70% by weight; more preferably from 1% to 65% by weight, especially from 5% to 60% by weight, and for example from 10% to 60% by weight, relative to the total weight of the phytosanitary (agro) formulation.

[0092] According to a specific embodiment of the invention (concentrate composition), the total content of one or more agro (phytosanitary) active compounds in the agricultural (phytosanitary) formulation ranges from 5% to 90% by weight, preferably from 5% to 70% by weight, more preferably from 5% to 60% by weight, and especially from 10% to 60% by weight, relative to the total weight of the agricultural (phytosanitary) formulation.

[0093] According to another specific embodiment of the invention (dilute composition), the total content of one or more agro (phytosanitary) active compounds in the agricultural (phytosanitary) formulation ranges from 0.01% to 3% by weight, preferably from 0.05% to 2% by weight, and more preferably from 0.1% to 1% by weight, relative to the total weight of the agricultural (phytosanitary) formulation.

[0094] Generally, relative to the total weight of the phytosanitary (agrochemical) formulation, the compound or the mixture of the compounds according to the invention accounts for 10% to 99.9% by weight, preferably 10% to 99% by weight, more preferably 20% to 95% by weight, especially 30% to 90% by weight, for example 30% to 80% by weight.

[0095] In an embodiment, the phytosanitary (agricultural) formulation according to the invention further comprises a fertilizer and / or a fertilizer stabilizer, especially a nitrogen fertilizer and / or a nitrogen fertilizer stabilizer. The fertilizer stabilizer can be N-(n-butyl) thiophosphoric triamide (NBPT) and / or dicyandiamide (DCD).

[0096] In another embodiment, the phytosanitary formulation further comprises at least one biostimulant, one plant growth regulator, one natural plant defense enhancer and / or one inoculant.

[0097] The compounds according to the invention advantageously exhibit good solubility properties.

[0098] The invention also relates to the use of the compounds of the invention as solvents, cosolvents and / or crystallization inhibitors, in particular in agricultural (phytosanitary) formulations comprising active ingredients (in particular biocides) and in fertilizer formulations comprising fertilizers and / or fertilizer stabilizers, in particular nitrogen fertilizers and / or nitrogen fertilizer stabilizers and / or urease inhibitors and / or nitrification inhibitors.

[0099] The compounds of the invention can also be used as a coalescing agent, for example in aqueous paint formulations.

[0100] The compounds of the invention can be used in agricultural formulations comprising active ingredients (such as biocides).

[0101] The compounds of the invention can also be used in fertilizer formulations, preferably efficiency-enhanced fertilizer formulations, which comprise fertilizers and / or fertilizer stabilizers, in particular nitrogen fertilizers and / or nitrogen fertilizer stabilizers and / or urease inhibitors and / or nitrification inhibitors.

[0102] The term solvent can in particular denote a product which is liquid at the temperature of use and which can contribute to making a solid substance liquid or to preventing / delaying the solidification or crystallization of a material in liquid form. It generally can have a melting point of less than or equal to 20 °C, in particular 5 °C, for example 0 °C.

[0103] Several agricultural (phytosanitary) active compounds can be combined in the agricultural (phytosanitary) formulations of the invention comprising the compounds of the invention or mixtures of the compounds of the invention.

[0104] The compounds of the invention can generally also be used as an alternative to potentially toxic solvents such as DMSO (dimethyl sulfoxide), NMP (N-methyl-2-pyrrolidone), DMF (N,N-dimethylformamide), DMAc (N,N-dimethylacetamide), in particular for dissolving polymers, or as other polar and ecologically friendly solvents such as NBP (N-butyl-2-pyrrolidone), (dihydrolevoglucosenone), PolarClean, N,N-dimethyl lactamide and an alternative to ADMA 10.

[0105] The agricultural (phytosanitary) formulations according to the invention can optionally comprise at least one biostimulant.

[0106] The term "biostimulant" preferably is intended to mean a compound which can enhance metabolic or physiological processes such as respiration, photosynthesis, nucleic acid uptake, ion uptake, nutrient delivery, or a combination thereof.

[0107] Typically, this is a substance or microorganism that, when applied to seeds, plants, or the rhizosphere, can stimulate natural processes to enhance or benefit nutrient uptake, nutrient use efficiency, tolerance to abiotic stress, or crop quality and yield.

[0108] Non-limiting examples of biostimulants include seaweed extracts (e.g., Ascophyllum nodosum), humic acids (e.g., potassium humate), fulvic acids, inositol, glycine, and combinations thereof.

[0109] The agricultural (phytosanitary) formulation according to the invention may optionally comprise at least one plant growth regulator.

[0110] Plant growth regulator means an active ingredient used to affect the growth characteristics of plants. Examples of plant growth regulators that can be used in the present invention include, but are not limited to: 1-naphthaleneacetic acid, 1-naphthaleneacetic acid salts, 1-naphthol, 2,4-dichlorophenoxyacetic acid (2,4-D), 2,4-DB, 2,4-DEP, 2,3,5-triiodobenzoic acid, 2,4,5-trichlorophenoxyacetic acid, 2-naphthoxyacetic acid, sodium 2-naphthoxyacetate, 3-chloro-4-hydroxyphenylacetic acid, 3-indoleacetic acid, 4-biphenylacetic acid, 4-chlorophenoxyacetic acid (4-CPA), 4-hydroxyphenylacetic acid, 6-benzylaminopurine, auxindole, α-naphthaleneacetic acid K-salt, β-naphthoxyacetic acid, p-chlorophenoxyacetic acid, dicamba, 2,4-dichlorprop, 2,4,5-fenoprop, indole-3-acetic acid (IAA), indole-3-acetyl-DL-aspartic acid, indole-3-acetyl-DL-tryptophan, indole-3-acetyl-L-alanine, indole-3-acetyl-L-valine, indole-3-butyric acid (IBA), indole-3-butyric acid K-salt, indole-3-propionic acid; α-naphthaleneacetic acid, methyl indole-3-acetate, naphthylacetamide, naphthaleneacetic acid (NAA), phenylacetic acid, picloram, potassium naphthenate, sodium naphthenate, 4-hydroxyphenylethanol, 4-CPPU, 6-benzylaminopurine (BA), 6-(γ,γ-dimethylallylamino)purine (2iP), 2-iP-2HCl, adenine, adenine hemisulfate, benzyladenine, kinetin, meta-topolin, N6-benzoyladenine, N-benzyl-9-(2-tetrahydropyranyl)adenine (BPA), N-(2-chloro-4-pyridyl)-N-phenylurea, gibberellic acid (GA3), gibberellins, gibberellin A4+A7 (GA n), ethylene, and abscisic acid.

[0111] The agricultural formulation (or agrochemical formulation) according to the invention may optionally comprise at least one emulsifier.

[0112] An emulsifier is a reagent which is intended to promote emulsification after placing the formulation in the presence of water and / or stabilization of the emulsion (over time and / or at temperature), for example by avoiding phase separation.

[0113] Generally, the total amount of one or more emulsifiers in the agricultural (phytosanitary) formulation according to the invention ranges from 0.05% to 40% by weight, preferably from 0.1% to 35% by weight, more preferably from 0.5% to 30% by weight, especially from 1% to 25% by weight, for example from 1% to 5% by weight, relative to the total weight of the agricultural (phytosanitary) formulation.

[0114] Generally, the agrochemical (phytosanitary) formulation according to the invention may further comprise at least one surfactant.

[0115] Advantageously, the surfactants which can be used in the present invention are selected from anionic, nonionic, cationic, amphoteric or zwitterionic surfactants, and mixtures thereof.

[0116] Preferably, the surfactant is selected from anionic surfactants, nonionic surfactants and mixtures thereof.

[0117] More preferably, the surfactant is selected from anionic surfactants, polyalkoxylated nonionic surfactants, and mixtures thereof.

[0118] The emulsifiers and surfactants which can be used are different from one or more agroactive compounds.

[0119] As examples of anionic surfactants, without any intended limitation thereof, mention may be made of:

[0120] - Alkylsulfonic acids, arylsulfonic acids, which are optionally substituted by one or more hydrocarbon groups and whose acid functional groups are partially or completely salified, such as C8 - C50 alkylsulfonic acids (more particularly C8 - C30, preferably C10 - C22 alkylsulfonic acids), benzenesulfonic acid, naphthalenesulfonic acid, substituted by one to three C1 - C30, preferably C4 - C16 alkyls and / or C2 - C30, preferably C4 - C16 alkenyls,

[0121] - Mono - or diesters of alkylsulfosuccinic acid, in which the straight - chain or branched - chain alkyl moiety is optionally substituted by one or more straight - chain or branched - chain C2 - C4 hydroxylated and / or alkoxylated (preferably ethoxylated, propoxylated, ethoxypropoxylated) groups,

[0122] - Phosphates, which are more particularly selected from those comprising at least one linear or branched, saturated, unsaturated or aromatic hydrocarbon radical, said hydrocarbon radical containing from 8 to 40, preferably from 10 to 30 carbon atoms and optionally substituted by at least one alkoxylated (ethoxylated, propoxylated, ethoxypropoxylated) group. Furthermore, they contain at least one monoesterified or diesterified phosphate group such that one or two free or partially or fully salified groups can be present. Preferred phosphates are of the monoester and diester type of the following: phosphoric acid and alkoxylated (ethoxylated and / or propoxylated) mono-, di- or tri-styrylphenols, or alkoxylated (ethoxylated and / or propoxylated) mono-, di- or tri-alkylphenols, optionally substituted by one to four alkyl groups; phosphoric acid and alkoxylated (ethoxylated or ethoxypropoxylated) C8-C30, preferably C10-C22 alcohols; phosphoric acid and non-alkoxylated C8-C22, preferably C10-C22 alcohols,

[0123] - Sulfates obtained from saturated or aromatic alcohols optionally substituted by one or more alkoxylated (ethoxylated, propoxylated, ethoxypropoxylated) groups and for which the sulfate functional group appears in free acid form or is partially or fully neutralized. As examples, mention may be made more particularly of sulfates obtained from saturated or unsaturated C8-C20 alcohols which may contain from 1 to 8 alkoxylated (ethoxylated, propoxylated, ethoxypropoxylated) units; sulfates obtained from polyalkoxylated phenols substituted by 1 to 3 saturated or unsaturated C2-C30 hydroxycarbon groups and in which the number of alkoxylated units is included between 2 and 40; sulfates obtained from polyalkoxylated mono-, di- or tri-styrylphenols (in which the number of alkoxylated units varies from 2 to 40).

[0124] The anionic surfactants can be in acid form (they are potentially anionic), or in partially or fully salified form with a counterion. The counterion can be an alkali metal (such as sodium or potassium), an alkaline earth metal (such as calcium), or furthermore even an ammonium ion of formula N(R)4+ where the R groups are identical or different and represent a hydrogen atom or a C1-C4 alkyl group optionally substituted by an oxygen atom.

[0125] As examples of nonionic surfactants, without any intended limitation thereto, mention may be made of:

[0126] - Polyalkoxylated (ethoxylated, propoxylated, ethopropoxylated) phenols which are substituted by at least one C4-C20, preferably C4-C12 alkyl or by at least one alkaryl (the alkyl part of which is a C1-C6 alkyl). More particularly, the total number of alkoxylation units is included between 2 and 100. By way of example, mention may be made of polyalkoxylated mono-, di- or tri-(phenylethyl) phenols, or polyalkoxylated nonylphenols. Among the ethoxylated and / or propoxylated, sulfated and / or phosphorylated di- or tri-styrenylphenols, mention may be made of ethoxylated di-(phenyl-1-ethyl) phenol containing 10 oxyethylene units; ethoxylated di-(phenyl-1-ethyl) phenol containing 7 oxyethylene units; sulfated ethoxylated di-(phenyl-1-ethyl) phenol containing 7 oxyethylene units; ethoxylated tri-(phenyl-1-ethyl) phenol containing 8 oxyethylene units; ethoxylated tri-(phenyl-1-ethyl) phenol containing 16 oxyethylene units; sulfated ethoxylated tri-(phenyl-1-ethyl) phenol containing 16 oxyethylene units; ethoxylated tri-(phenyl-1-ethyl) phenol containing 20 oxyethylene units; phosphorylated ethoxylated tri-(phenyl-1-ethyl) phenol containing 16 oxyethylene units.

[0127] - Polyalkoxylated (ethoxylated, propoxylated, ethopropoxylated) C6-C22 fatty acids or alcohols. The number of alkoxylation units is included between 1 and 60. The term ethoxylated fatty acids includes both products obtained by ethoxylating fatty acids with ethylene oxide and those obtained by esterifying fatty acids with polyethylene glycol.

[0128] - Polyalkoxylated (ethoxylated, propoxylated, ethopropoxylated) triglycerides of vegetable or animal origin. Thus, it may include triglycerides from lard, tallow, ground nut oil, butter, cottonseed oil, linseed oil, olive oil, palm oil, grape seed oil, fish oil, soybean oil, castor oil, rapeseed oil, coprah oil, coconut oil, and the total number of alkoxylation units included therein is between 1 and 60. The term ethoxylated triglycerides refers to both products obtained by ethoxylating triglycerides with ethylene oxide and those obtained by transesterifying triglycerides with polyethylene glycol.

[0129] - Sorbitan esters, which are optionally polyalkoxylated (ethoxylated, propoxylated, ethopropoxylated), more particularly cyclic sorbitan esters of C10-C20 fatty acids such as lauric acid, stearic acid or oleic acid, and the total number of alkoxylation units included therein is between 2 and 50.

[0130] Useful emulsifiers are in particular the following products, all of which are sold by the applicant:

[0131] - TSP / 724: Surfactant based on ethoxypropylated triphenylvinylphenol,

[0132] - 796 / P: Surfactant based on ethoxypropylated triphenylvinylphenol

[0133] - CY 8: Surfactant based on ethoxylated triphenylvinylphenol

[0134] - BSU: Surfactant based on ethoxylated triphenylvinylphenol

[0135] - S / 25: Surfactant based on ethoxylated triphenylvinylphenol

[0136] - 3D33: Surfactant based on ethoxylated triphenylvinylphenol phosphate

[0137] - RC: Surfactant based on ethoxylated castor oil

[0138] - OR / 36: Surfactant based on ethoxylated castor oil

[0139] - VO2003: Surfactant based on ethoxylated castor oil

[0140] - OL40: Surfactant based on ethoxylated sorbitan hexaoleate

[0141] - T / 20: Surfactant based on ethoxylated sorbitan ester.

[0142] - TBE724: Surfactant based on ethoxypropylated triphenylvinylphenol

[0143] - TEB25: Mixture of surfactants based on ethoxylated castor oil, calcium dodecylbenzenesulfonate and alkoxylated polymer

[0144] - 60 / B: Surfactant based on dodecylbenzenesulfonate

[0145] - 60 / BE: Surfactant based on dodecylbenzenesulfonate.

[0146] Typically, the total amount of one or more surfactants in the agricultural (phytosanitary) formulation according to the invention ranges from 0.05% to 40% by weight, preferably from 0.1% to 35% by weight, more preferably from 0.5% to 30% by weight, especially from 1% to 25% by weight, for example from 1% to 5% by weight, relative to the total weight of the agricultural (phytosanitary) formulation.

[0147] Typically, the total amount of one or more anionic surfactants in the agricultural (phytosanitary) formulation according to the invention ranges from 0.05% to 40% by weight, preferably from 0.1% to 35% by weight, more preferably from 0.5% to 30% by weight, especially from 1% to 25% by weight, for example from 1% to 5% by weight, relative to the total weight of the agricultural (phytosanitary) formulation.

[0148] Typically, the total amount of one or more nonionic surfactants, especially one or more polyalkoxylated nonionic surfactants, in the agricultural (phytosanitary) formulation according to the invention ranges from 0.05% to 40% by weight, preferably from 0.1% to 35% by weight, more preferably from 0.5% to 30% by weight, especially from 1% to 25% by weight, for example from 1% to 5% by weight, relative to the total weight of the agricultural (phytosanitary) formulation.

[0149] The phytosanitary (agricultural) formulation according to the invention may optionally further comprise a co-solvent which is at least one compound different from the compounds of the invention.

[0150] Such other solvents or co-solvents are generally selected from:

[0151] - straight-chain or branched, saturated or unsaturated aliphatic hydrocarbons which may contain halogen atoms, phosphorus atoms, sulfur atoms and / or nitrogen atoms and / or functional groups,

[0152] - carbocyclic or heterocyclic hydrocarbons, either of which is saturated, unsaturated or aromatic, which may contain halogen atoms, phosphorus atoms, sulfur atoms and / or nitrogen atoms and / or functional groups,

[0153] More particularly, this co-solvent is selected from:

[0154] - alkanes, cycloalkanes and aromatic derivatives, such as paraffins with a branched or straight chain such as "white oil" or decalin; mono-, di- or tri-alkylbenzenes or naphthalenes, compounds sold under the names 100, 150, 200 standard and ND grades;

[0155] - aliphatic, alicyclic or aromatic mono-esters, di-esters or tri-esters, such as alkyl esters of alkanoic acids like methyl oleate; benzyl esters of alkanoic acids; alkyl benzoates; γ-butyrolactone; ε-caprolactone; esters of glycerol and citric acid; alkyl salicylates; phthalates; dibenzoates; acetoacetates; glycol ether acetates, dipropylene glycol diacetate;

[0156] - mono-, di- or tri-alkyl phosphates, such as triethyl phosphate; tributyl phosphate; or tri-2-ethylhexyl phosphate;

[0157] - aliphatic, alicyclic or aromatic ketones, such as dialkyl ketones; benzyl ketones; fenchone; acetophenone; cyclohexanone; alkyl cyclohexanones;

[0158] - aliphatic, alicyclic or aromatic alcohols, such as diols; 2-ethylhexanol; cyclohexanol; benzyl alcohol; tetrahydrofurfuryl alcohol;

[0159] - aliphatic, alicyclic or aromatic ethers, such as ethers of diols, notably ethylene glycol and propylene glycol and their polymers; diphenyl ether, diphenyl ether of dipropylene glycol; monomethyl ether or monobutyl ether, monobutyl ether of tripropylene glycol; alkoxyalkanols; dimethyl isosorbide;

[0160] - fatty acids, such as linoleic acid, linolenic acid, oleic acid;

[0161] - carbonates, such as propylene carbonate or butylene carbonate; lactates; fumarates, succinates, adipates, maleates;

[0162] - amides, such as alkyldimethylamides, dimethyl-decanamide;

[0163] - alkylureas;

[0164] - amines, such as alkanolamines, morpholine; N-alkyl-pyrrolidone;

[0165] - tetramethyl sulfone;

[0166] - dimethyl sulfoxide;

[0167] - halogenated alkanes or halogenated aromatic solvents, such as chlorinated alkanes or chlorobenzene.

[0168] Crystallization inhibitors can also be present in the phytosanitary (agricultural) formulations according to the invention. The crystallization inhibitors can be the co-solvents mentioned above. The crystallization inhibitors can also be non-polyalkoxylated fatty alcohols or fatty acids (for example, products sold by the applicant can be mentioned OL700), alkanolamides, polymers.

[0169] The agricultural (phytosanitary) formulation according to the invention may further contain one or more additives different from the components previously described, and these additives are preferably selected from viscosity regulators, suspending agents, antifoaming agents and defoaming agents (especially silicone antifoaming agents and defoaming agents), anti-cratering agents, anti-leaching agents, penetration aids, inert fillers (especially mineral fillers), binders, diluents, antifreeze agents, stabilizers, dyes, emetics, tackifiers (adhesion promoters), absorbents, dispersants, disintegrants, wetting agents, preservatives and / or antimicrobial agents.

[0170] Each additive may be present in the agricultural (phytosanitary) formulation according to the invention in an amount in the range of 0% to 20% by weight, preferably 0% to 10% by weight, relative to the total weight of the agricultural formulation. Each additive may be present, for example, in an amount in the range of 0.1% to 20% by weight, especially 0.1% to 10% by weight, relative to the total weight of the formulation in the agricultural (phytosanitary) formulation according to the invention. Each additive may be present in the agrochemical (phytosanitary) formulation according to the invention in an amount preferably in the range of 0% to 5% by weight, notably 0.1% to 5% by weight, relative to the total weight of the formulation. Those skilled in the art will be able to select these optional additives and their amounts such that they do not impair the properties of the agricultural (phytosanitary) formulation of the invention.

[0171] Advantageously, the agricultural (phytosanitary) formulation according to the invention is in liquid form at 20 °C and atmospheric pressure (i.e., 1.013 x 10 5 Pa) and may be in the form of a concentrate, a diluted concentrate or a sprayable dilution of one or more agro(phytosanitary) active compounds.

[0172] Depending on the different agro(phytosanitary) active compounds, different types of formulations may be used. The formulations that can be used depend on the physical form of the agro(phytosanitary) active material (e.g., solid or liquid) and their physicochemical properties in the presence of other compounds (such as water or solvents).

[0173] For practical reasons (e.g., for ease of handling), it may be preferable to use formulations in liquid form. Depending on the physicochemical properties of the one or more different agro(phytosanitary) active compounds under consideration, the formulations may be in the following forms: emulsifiable concentrate (EC), concentrated emulsion in water (EW), microemulsion (ME), suspoemulsion (SE), oil dispersion (OD), dispersible concentrate (DC), suspension concentrate (SC), capsule suspension (CS), soluble liquid (SL), flowable concentrate for seed treatment (FS).

[0174] Preferably, the agricultural (phytosanitary) formulation according to the invention is in the form of: emulsifiable concentrate (EC), concentrated emulsion in water (EW), microemulsion (ME), suspoemulsion (SE), oil dispersion (OD), dispersible concentrate (DC), capsule suspension (CS), soluble liquid (SL).

[0175] More preferably, the agricultural (phytosanitary) formulation according to the invention is in the form of: emulsifiable concentrate, concentrated emulsion in water, concentrated microemulsion, concentrated suspoemulsion, concentrated oil dispersion or dispersible concentrate.

[0176] In a specific embodiment, the agricultural (phytosanitary) formulation according to the invention is in the form of an emulsifiable concentrate (EC).

[0177] The agricultural (phytosanitary) formulation according to the invention is generally a concentrated agrochemical (phytosanitary) formulation and is intended to be spread on cultivated fields or fields to be cultivated, most often after dilution with water in order to obtain a diluted composition. The dilution is generally carried out directly by the farm operator in a bucket ("tank mix"), for example in the bucket of a device intended to spread the composition. This does not exclude the possibility that the farm operator adds other plant protection products such as fungicides, herbicides, pest control agents, insecticides, fertilizers, adjuvants, etc. Thus, the formulation can be used to prepare a formulation of one or more agrochemical (phytosanitary) active compounds diluted in water by mixing at least one weight part of the concentrated formulation with at least 10 parts, preferably less than 10,000 parts of water. The dilution ratio and amount to be applied to the field generally depend on one or more agrochemical (phytosanitary) active compounds and the desired dose for treating the field (which can be determined by the farm operator).

[0178] According to one embodiment of the invention, the agrochemical (phytosanitary) formulation according to the invention is aqueous.

[0179] According to this embodiment, the water content of the agricultural (phytosanitary) formulation preferably ranges from 5% to 99% by weight, more preferably from 20% to 95% by weight, even more preferably from 25% to 90% by weight, especially from 25% to 85% by weight, for example from 25% to 70% by weight, relative to the total weight of the agricultural (phytosanitary) formulation.

[0180] According to this embodiment, the pH preferably ranges from 1 to 11, and in particular from 2.5 to 9.5.

[0181] The pH of the formulation can be adjusted to the desired value by means of an alkalizing agent or an acidifying agent. Among the alkalizing agents, one or more bases such as ammonia, sodium hydroxide or ethanolamine can be used. Among the acidifying agents, for example, inorganic acids or organic acids such as hydrochloric acid or orthophosphoric acid can be mentioned.

[0182] According to a specific embodiment of the invention, a phytosanitary (agricultural) formulation can advantageously comprise:

[0183] a) at least one agricultural (phytosanitary) active compound (either only one agricultural (phytosanitary) active compound or a combination of different agricultural (phytosanitary) active compounds), preferably at least one pest control agent, in an amount of from 0.01% to 90% by weight, preferably from 5% to 60% by weight, based on the total weight of the phytosanitary (agricultural) formulation;

[0184] b) a compound according to the invention or a mixture of compounds according to the invention in an amount of from 5% to 90% by weight, preferably from 10% to 90% by weight, in particular from 30% to 90% by weight, for example from 30% to 80% by weight, based on the total weight of the phytosanitary (agricultural) formulation;

[0185] c) optionally, at least one of said co-solvents in an amount of from 0.1% to 40% by weight, preferably from 1% to 30% by weight, based on the total weight of the phytosanitary (agricultural) formulation;

[0186] d) at least one surfactant in an amount of from 0.05% to 40% by weight, preferably from 0.1% to 35% by weight, more preferably from 0.5% to 30% by weight, in particular from 1% to 25% by weight, for example from 1% to 5% by weight, based on the total weight of the phytosanitary (agricultural) formulation;

[0187] e) optionally, water in an amount of from 5% to 90% by weight, preferably from 10% to 80% by weight, in particular from 25% to 70% by weight, based on the total weight of the phytosanitary (agricultural) formulation.

[0188] The known conventional methods for preparing agricultural (phytosanitary) formulations can be carried out. This can be achieved by simply mixing the components.

[0189] The agricultural (phytosanitary) formulation according to the invention can be used for killing or inhibiting pests and / or removing unwanted plants and / or inhibiting the growth of unwanted plants.

[0190] The agricultural (phytosanitary) formulations according to the invention can be diluted and applied to at least one plant, the area adjacent to the plant, the soil suitable for supporting plant growth, the roots of the plant, the leaves of the plant, and / or the seeds suitable for growing plants in a conventional manner; for example, by watering (sprinkling), drip irrigation, spraying, and / or atomization.

[0191] In the above description, all preferred embodiments regarding the components can be used alone or in combination.

[0192] As described above, the compounds of the present invention can generally also be used as alternatives to polar solvents such as NMP, DMF, DMSO, acetophenone, and DMAc, especially for dissolving polymers. For example, these solvents can be used during the wet coating of electrodes (such as electrodes for automotive batteries) with polymer binders such as PVDF (polyvinylidene fluoride) and carbon materials. The compounds of the present invention can also be used in other coating applications, the manufacture of membranes, or solid batteries. It can also be used as a solvent during the recycling process of polymers, especially chemically resistant polymers like PVDF or PVDC (polyvinylidene chloride), still as an alternative to the above solvents. It can also be used to prepare polycondensates in solution, especially polyimides or polyesters or polyamides or polyamide-imides, especially partially or fully aromatic polycondensates such as aromatic polyamides (aramids). Finally, it can also be used as a cleaning solvent for cleaning equipment such as reactors, especially polymerization reactors.

[0193] Since the compounds of the present invention are advantageously eco-friendly solvents and preferably have very good safety and sustainability characteristics, they can also be used as solvents in household care formulations, for household or public areas (hotels, offices, factories, etc.). They can be formulations for cleaning hard surfaces such as floors, furniture surfaces, and the surfaces of kitchen and bathroom fittings, or tableware. These formulations can also be used in the industrial field for degreasing the manufactured products and / or for cleaning them.

[0194] Examples

[0195] Example 1

[0196] Synthesis of 3-(2,4-dimethyl-1,3-dioxolan-2-yl)-N,N-dimethylpropanamide

[0197] Ketalization of methyl levulinate with 1,2-propanediol

[0198] At room temperature, add to a 1L double-jacketed reactor equipped with a temperature probe, a mechanical stirrer (a propeller with 3 inclined plows), baffles, a cooler (5°C), and a Dean-Stark apparatus:

[0199] - 500 mL of toluene.

[0200] -150.47 g of methyl levulinate (1.16 moles, 1 equivalent).

[0201] -218.38 g of 1,2-propanediol (2.87 moles, 2.5 equivalents).

[0202] The reaction medium (which is biphasic at room temperature) was then allowed to stir at 515 rpm, and then the temperature of the reaction mass was raised to 107 °C. At this temperature, the solution became homogeneous and transparent.

[0203] Then the catalyst methanesulfonic acid (1.5 mL, 2.22 g, 23.05 mmol, 2 mol%) was added to the solution in one portion, causing significant reflux of the reaction mass. After the introduction of the catalyst, water was formed and its condensation into the Dean-Stark apparatus was observed.

[0204] The reaction mixture was then allowed to stir under reflux (109 °C - 110 °C) for 3 hours 15 minutes until no more water condensed into the Dean-Stark apparatus. At this stage of the reaction, the crude 1 1H NMR analysis showed that 75% of the ketone was converted to the ketal and significant transesterification by-products with 1,2-propanediol were formed. The reaction mixture was then allowed to cool at room temperature and the catalyst was neutralized by adding 200 mL of saturated aqueous NaHCO3.

[0205] The phases were decanted and separated, and the organic phase was washed 4 times with 200 mL of saturated aqueous NaHSO3 in order to selectively remove the ketone product from the organic phase by reversibly and selectively forming water-soluble α-hydroxy sulfonate derivatives.

[0206] Finally, the organic phase was washed with 200 mL of brine and 200 mL of water.

[0207] The organic phase was then dried over MgSO4, filtered, and the solvent was removed under vacuum to afford 144.7 g of a crude material as an oil.

[0208] The crude 1 1H NMR analysis showed that the product contained approximately 96 mol% of the ketal (where 4 mol% was the ketone), and 44 mol% of the ketal had undergone transesterification with 1,2-propanediol. Therefore, in order to convert the transesterification by-products back to the desired methyl ester, the crude was directly involved in a base-catalyzed transesterification reaction in MeOH.

[0209] The transesterification was carried out as follows:

[0210] At room temperature, in a 1 L double-jacketed reactor equipped with a temperature probe, a mechanical stirrer (propeller with 3 pitched blades), baffles, and a cooler (5 °C), the following were added:

[0211] - 300 mL of methanol,

[0212] - 144.66 g of the crude material from the previous step,

[0213] - 1.158 g of sodium methoxide (0.8 wt% relative to the crude).

[0214] The mixture was then allowed to stir at 50 °C (500 rpm) for 15 minutes, and the reaction was allowed to proceed to completion as monitored by 1 1H NMR analysis.

[0215] The reaction mass was then cooled to room temperature, and 0.5 mL of aqueous H3PO4 solution (85 wt%) was added to the mixture to lower the pH to between 7.5 and 8 (in this case, 7.3 after 10% dilution in water at room temperature).

[0216] Methanol was removed under vacuum, and the crude was washed with 100 mL of saturated aqueous NaHCO3, 100 mL of saturated aqueous Na2SO3, and finally with 100 mL of water.

[0217] The crude was dried under vacuum (80 °C, 30 mbar) to recover 104.65 g of the desired methyl ketal levulinate.

[0218] 1 1H NMR analysis showed that the crude contained only 2 mol% of methyl levulinate and 98 mol% of the ketal and was allowed to proceed directly to the next step;

[0219] 1 1H NMR (CDCl3, 400 MHz) δ (ppm): 4.2 - 4.0 (m, 1H), 3.98 - 3.86 (m, 1H), 3.56 (s, 3H), 3.33 (t), 3.25 (t) (integral sum: 1H), 2.38 - 2.20 (m, 2H), 1.98 - 1.82 (m, 2H), 1.25 (s), 1.21 (s) (integral sum: 2H), 1.15 (d, 3H).

[0220] 13 13C (CDCl3, 101 MHz) δ (ppm): 173.22, 173.14, 108.85, 108.72, 72.26, 71.30, 70.84, 70.47, 50.82, 50.77, 34.18, 33.89, 28.50, 28.06, 24.67, 23.84, 18.19, 17.38.

[0221] The ester functional group of methyl 3-(2,4-dimethyl-1,3-dioxolan-2-yl)propionate was then converted to an amide in a carefully dried vessel under an inert argon atmosphere as follows:

[0222] At room temperature, the following were added to a dry 1 L double-jacketed reactor equipped with a mechanical stirrer (propeller with 3 pitched blades), baffles, a temperature probe, and a cooler (5 °C):

[0223] - 103.08 g of the ketal methyl levulinate obtained in the previous step (assumed purity 100%, 0.55 mol),

[0224] - 582 mL of a DMA / MeOH solution (427.90 g, 2 M, 11 wt%, 1.04 mol, 1.9 eq).

[0225] The solution was then allowed to stir at room temperature (600 rpm) and 0.914 g of solid NaOMe (0.017 mol, 3 mol%) was added to the solution. The solution was then allowed to stir at 50 °C for 7 hours 00 minutes, and an additional amount of sodium methoxide (2.08 g, 7 mol%) was added to the solution. The mixture was then stirred at 50 °C for 62 hours 00 minutes. At this stage, the conversion of methyl levulinate to the desired N,N-dimethylamide reached >98%.

[0226] Volatiles (DMA and MeOH) were then removed under vacuum (65 °C, 400 mbar), and the catalyst in the residue was carefully neutralized by adding 3.8 g of an aqueous H3PO4 solution (85 wt%) at room temperature, followed by 3 mL of an aqueous NaOH solution (30 wt%) in order to lower the pH of the mixture to between 7.5 and 8 (final pH = 7.4, measured after 10 wt% dilution in water at room temperature). During this stage, it was important to keep the pH above 7 in order to avoid any acidic hydrolysis of the ketal to the ketone. A white precipitate formed after the addition of the aqueous H3PO4 (85%) solution.

[0227] The orange crude suspension obtained (101.7 g) was then filtered through diatomaceous earth to remove phosphates, and the solid was washed several times with ethyl acetate. The solvent of the filtrate was then removed under vacuum (60 °C, 30 mbar), giving 99.34 g of an orange oil. At this stage, the product still contained some inorganic salts.

[0228] Then, finally, 1 L of ethyl acetate (containing 0.1 wt% Et3N) was used as the eluent to filter the oil over silica gel in order to remove traces of inorganic salts and for decolorization. The solvent was then evaporated under vacuum (80 °C, 15 mbar) to afford the final product as a pale yellow oil (m = 86.93 g), corresponding to a separation yield of 79%.

[0229] 1 1H NMR (CDCl3, 400 MHz) δ (ppm): 4.3 - 4.15 (m, 1H), 4.09 - 4.05 (m, 1H), 3.47 - 3.36 (m, 1H), 3.07 (s, 3H), 2.92 (s, 3H), 2.49 - 2.42 (m, 2H), 1.96 - 1.89 (m, 2H), 1.34 (s), 1.31 (s) (sum of two diastereoisomers = 3H), 1.23 (d), 1.22 (d) (integration sum = 3H). 13 13C NMR (CDCl3, 101 MHz) δ (ppm): 175.51, 175.43, 110.97, 110.84, 74.2, 73.33, 72.4, 72.1, 37.95, 36.28, 35.96, 35.73, 29.24, 28.95, 25.6, 24.64, 19.09, 18.59.

[0230] Example 2

[0231] Solubility of different single fungicides

[0232] In Example 2, the solubility of the fungicides was measured at 24 °C and at 0 °C after inoculation in 3-(2,4-dimethyl-1,3-dioxolan-2-yl)-N,N-dimethylpropanamide (Example 1) and in prior art solvents. The concentration (w / v) of the fungicides was increased at 5% intervals and the highest still soluble concentration is stated in the table below.

[0233] Table 1: Maximum solubility (w / v) of different fungicides in the solvent of Example 1 and in prior art solvents at 24 °C (and at 0 °C after inoculation in parentheses).

[0234]

[0235]

[0236] Example 3

[0237] Solubility of different combined fungicides:

[0238] In Example 3, the solubility of the fungicide combination formulations was measured at 24 °C in the ketal - amide derivative of Example 1 (3-(2,4 - dimethyl - 1,3 - dioxolan - 2 - yl)-N,N - dimethylpropanamide) and in prior art solvents. As can be seen from Table 2, the ketal - amide of Example 1 is an effective solvent for the combination pesticidal formulations. In addition, the solubility tests showed that for specific combinations (such as azoxystrobin / fluxapyroxad), the ketal - amide of Example 1 is a better solvent than PolarClean and ADMA 10.

[0239] Table 2: Solubility of different combination fungicide formulations (“Combi”) at 24 °C.

[0240] “A” represents azoxystrobin, “T” represents tebuconazole, “P” represents prothioconazole, “F” represents “fluxapyroxad”, “l” represents a clear and transparent solution, “n” represents insolubility

[0241]

[0242] Example 4

[0243] Solubility of the urease inhibitor NBPT

[0244] The solubility of NBPT was measured at 24 °C and - 5 °C in NBP, Cyrene TM and PolarClean and in the solvent of Example 1. The results are depicted in Table 3 below. As can be seen, the solvent of Example 1 is an excellent solvent for dissolving NBPT. On the other hand, the use of Cyrene and NBP results in yellow discoloration even at low concentrations, and the resulting solutions are highly viscous even at 35% (w / v), thus making the resulting solutions difficult to use and further process. In addition, it can be seen that for dissolving NBPT, the ketal - amide solvent of Example 1 is significantly better than PolarClean. Without being bound by theory, it is believed that the increased solubility in the ketal - amide solvent of Example 1 may be due to favorable enthalpy - driven dissolution, which is due to the formation of H - bonds between the hydrogen groups of the amide functional group of NBPT and the ketone functional group of the solvent.

[0245] Table 3: Maximum solubility (w / v) of NBPT in the solvent of Example 1, NBP and Cyrene TM at 24 °C (and at - 5 °C in parentheses).

[0246]

[0247] Example 5

[0248] Solubility of Different Polymers

[0249] As a solvent for dissolving polymers, the ketal - amide of levulinic acid of Example 1 as an NMP alternative was tested. The results are presented in Table 4 below. As can be seen, the ketal - amide of levulinic acid of Example 1 is a suitable alternative to the solvent NMP and can be used for manufacturing battery electrodes for solid - state batteries or Li - ion batteries or for coatings or for producing antifouling membranes for a wide range of filtration applications. PVDF and are polymer binders which are typically dissolved in NMP (or DMF and DMAc) and then used to dispense a slurry of carbon material and the dissolved binder (also called wet coating) onto a substrate material: the electrode. Using the ketal - amide of levulinic acid instead of NMP during the manufacture of electrodes (such as those for automotive batteries) is environmentally friendly.

[0250] PVDF( 1015) is also used to manufacture microfiltration and ultrafiltration membranes for a wide range of filtration applications by the NIPS process (non - solvent induced phase separation). In NIPS, the polymer solution membrane is immersed in a non - solvent bath (water), inducing the membrane to phase - separate into a polymer - rich phase that becomes the membrane matrix and a polymer - poor phase that becomes the membrane pores. N - methyl - 2 - pyrrolidone (NMP) is used as the solvent medium because it can successfully dissolve PVDF. Using the ketal - amide of levulinic acid instead of NMP during the manufacture of the membrane is environmentally friendly.

[0251] Polyamide - imide PAI is used as a high - performance coating material in both the automotive industry and high - end household appliances. The main requirement here is to find a good solvent to achieve a liquid - form coating formulation. NMP, DMF, and DMAC are considered good solvents for such polymers. Using the ketal - amide of levulinic acid instead of NMP during the manufacture of the membrane is environmentally friendly.

[0252] Table 4: Solubility of Different Polymers (PVDF (polyvinylidene fluoride) polymer, fluoroelastomer, and PAI (polyamide - imide)) in the ketal - amide of levulinic acid of Example 1.

[0253]

[0254] Example 6

[0255] Synthesis of 3-(4-(hydroxymethyl)-2-methyl-1,3-dioxolan-2-yl)-N,N-dimethylpropanamide

[0256] The reaction was carried out in a carefully dried container and under an inert nitrogen atmosphere.

[0257] At room temperature, the following were added to a carefully dried 1 L double-jacketed reactor equipped with a mechanical stirrer (propeller with 3 pitched blades), baffles, a temperature probe, and a cooler (5 °C):

[0258] 86.8 g of ethyl glyceryl-ketone levulinate (0.40 mol, 1 eq) obtainable according to the protocol described in Example 6 of WO 2012 / 018939 by using methanesulfonic acid instead of 2-naphthalenesulfonic acid as the catalyst,

[0259] 397.7 mL of a DMA / MeOH solution (308.2 g, 2 M, 11 wt%, 0.795 mol, 2 eq).

[0260] The solution was then allowed to stir at room temperature (650 rpm) and 0.678 g of solid NaOMe (0.012 mol, 3 mol%) was added to the solution in one portion. The solution was then allowed to stir at 50 °C (600 rpm) for 3 hours 00 minutes. At this stage, 1H NMR analysis showed that the level of ester conversion to the desired amide product reached 20 mol%. To accelerate the reaction kinetics, an additional amount of solid sodium methoxide (1.58 g, 0.028 mol, 7 mol%) was added to the solution. The mixture was then stirred at 50 °C for 48 hours 00 minutes, allowing an ester conversion to amide of 96 mol% to be reached.

[0261] Volatiles (DMA, MeOH, and ethanol) were then removed under vacuum (60 °C, 2 mbar, 307.2 g of collected distillate), and the catalyst in the residue was carefully neutralized by adding 1.834 g of H3PO4 (85 wt% aqueous solution, 0.016 mol, 0.4 eq relative to NaOMe) at room temperature in order to lower the pH of the mixture to between 7.5 and 8.5 (final pH = 7.41, measured after 2 wt% dilution in water at room temperature). During this stage, it was important to keep the pH above 7 in order to avoid any acidic hydrolysis of the ketal to the ketone. No white precipitate was observed to form in this case after the addition of the H3PO4 (85%) aqueous solution.

[0262] The obtained residue was then heated at 70 °C under 13 mbar vacuum in order to remove all volatiles that had formed during the catalyst and the step, mainly methanol residues as well as ethanol and water. Finally, the crude product was diluted with the minimum amount of ethyl acetate containing 0.1 wt% triethylamine. After addition of ethyl acetate, phosphate precipitation was observed. The suspension was then filtered over silica gel and eluted using 1 L of ethyl acetate as eluent (containing 0.1 wt% Et3N) in order to remove trace amounts of inorganic salts and for decolorization. The solvent was then evaporated under vacuum (80 °C, 10 mbar) to afford the final product as a viscous yellow oil (m = 75 g), corresponding to an 85% isolated yield.

[0263] 1H NMR analysis showed that the desired ketal amide content was 98.5 wt% and the product additionally contained 1.5 wt% of N,N-dimethylacetoacetamide as a by-product (acid value = 4.2 mg(KOH) / g, Karl-Fisher: 0.2 wt% H2O).

[0264] 1H NMR (CDCl3, 400 MHz) δ (ppm): 4.24 - 4.11 (m, 1H), 4.08 - 4.04 (m, 1H), 3.77 - 3.7 (m, 1H), 3.63 - 3.54 (m, 2H), 3.07 (s, 3H), 2.92 (s, 3H), 2.52 - 2.42 (m, 2H), 1.99 - 1.91 (m, 2H), 1.36 (s), 1.32 (s) (sum of two diastereoisomers = 3H).

[0265] 13C NMR (CDCl3, 101 MHz) δ (ppm): 175.62, 175.37, 111.47, 111.25, 78.57, 77.75, 67.67, 67.57, 63.96, 63.67, 37.95, 35.96, 35.91, 35.31, 29.22, 28.83, 25.25, 24.23.

[0266] Example 7

[0267] Solubility of different fungicides

[0268] In Example 7, the solubility of the fungicides was measured at 24 °C in 3-(4-(hydroxymethyl)-2-methyl-1,3-dioxolan-2-yl)-N,N-dimethylpropanamide (Example 6) and in solvents of the prior art.

[0269] Table 5: Maximum solubility (w / v) of different fungicides in the solvent of Example 6 and in solvents of the prior art at 24 °C.

[0270]

[0271] Example 8

[0272] Solubility of the urease inhibitor NBPT

[0273] In addition to the previous measurements in NBP, Cyrene TM and PolarClean (Example 4), the solubility of NBPT was also measured in the solvent of Example 6 at 24 °C. The results are depicted in Table 6 below. As can be seen, the solvent of Example 6 is a very good solvent for dissolving NBPT. As mentioned in Example 4, on the other hand, the use of Cyrene and NBP results in yellow discoloration even at low concentrations, and the resulting solution is highly viscous even at 35% (w / v), thus making the resulting solution difficult to use and further process. In addition, it can be seen that for dissolving NBPT, the ketal-amide solvent of Example 6 is better than PolarClean.

[0274] Table 6: Maximum solubility (w / v) of NBPT in the solvent of Example 6, NBP and Cyrene TM at 24 °C

[0275]

Claims

1. A compound having the formula (I): wherein R 1 and R 2 are independently selected from -(C1-C6)alkyl, including -(C1)alkyl, -(C2)alkyl, -(C3)alkyl, -(C4)alkyl, -(C5)alkyl, and -(C6)alkyl, which may optionally be interrupted and / or substituted by a heteroatom or a heteroatom-containing group, or R 1 and R 2 form a heterocycle containing 4 to 8 atoms with a nitrogen atom; and R 3 is hydrogen, or a -(C1-C4)alkyl group which is optionally interrupted and / or substituted by a heteroatom or a heteroatom-containing group; Provided that when R 1 and R 2 is -CH3, then R 3 is not hydrogen.

2. The compound according to claim 1, Among them, R 1 and R 2 are independently selected from -(C1-C3) alkyl, including -(C1) alkyl, -(C2) alkyl, and -(C3) alkyl.

3. The compound according to claim 1 or 2, Among them, R 3 is a -(C1-C2) alkyl group, including -(C1) alkyl and -(C2) alkyl, which is optionally interrupted and / or substituted by a heteroatom, where the heteroatom is preferably oxygen.

4. The compound according to any one of claims 1 to 3, wherein R 3 is a -(C1)alkyl group, optionally substituted with a heteroatom.

5. The compound according to claim 1, wherein, R 1 and R 2 are independently selected from -(C1-C6) alkyl, preferably selected from -(C1-C3) alkyl, and R 3 is a -(C1-C4)alkyl group, preferably a -(C1-C2)alkyl group, which is optionally interrupted and / or substituted by a heteroatom or a heteroatom-containing group.

6. The compound according to claim 1, wherein, R 1 and R 2 are independently selected from -(C1)alkyl, -(C2)alkyl, and -(C3)alkyl, and R 3 is a -(C1-C4) alkyl group, preferably a -(C1-C2) alkyl group.

7. The compound according to claim 1, wherein, R 1 and R 2 are independently selected from -(C1)alkyl, -(C2)alkyl, and -(C3)alkyl, and R 3 is a -(C1-C2) alkyl group, preferably a -(C1) alkyl group.

8. The compound according to claim 7, wherein, R 1 、R 2 and R 3 are -(C1) alkyl groups.

9. The compound according to claim 1, wherein, R 1 and R 2 are independently selected from -(C1)alkyl, -(C2)alkyl, and -(C3)alkyl, and R 3 is -CH2-OH.

10. The compound according to claim 9, wherein, R 1 and R 2 is -(C1) alkyl.

11. A process for producing a compound according to any one of claims 1 to 10 from levulinic acid or its esters or salts, the process comprising at least the following steps in any order: (a) Ketalization with a compound having the formula R 3 -CH(OH)-CH2OH (b) amidation with an amine having the formula HNR 1 R 2 and wherein R 1 to R 3 is as defined above.

12. The method according to claim 11, wherein, Step (a) is acid-catalyzed and step (b) is base-catalyzed.

13. The method according to claim 12, wherein, Step (b) further comprises neutralization of the base, preferably carried out with an ion exchange resin.

14. A composition comprising a compound according to any one of claims 1 to 10.

15. The composition according to claim 14, which is at least part of a phytosanitary formulation, a cleaning formulation, a stripping formulation, a degreasing formulation, a lubricant or textile formulation, a coating formulation such as a paint formulation or a pigment or ink formulation.

16. The composition according to claim 15, which is a phytosanitary formulation, the phytosanitary formulation comprising: a) a phytosanitary active compound; b) a compound according to any one of claims 1 to 10; c) optionally at least one emulsifier, preferably a surfactant; d) optionally water.

17. The composition according to claim 15, which is a phytosanitary formulation, the phytosanitary formulation comprising: a) at least one agroactive compound, preferably at least one pest control agent, in an amount of from 0.01% to 90% by weight, preferably from 5% to 60% by weight, based on the total weight of the phytosanitary formulation; b) a compound according to any one of claims 1 to 4 or a mixture of compounds according to any one of claims 1 to 4 in an amount of from 5% to 90% by weight, preferably from 10% to 90% by weight, in particular from 30% to 90% by weight, for example from 30% to 80% by weight, based on the total weight of the phytosanitary formulation; c) optionally at least one of said cosolvents in an amount of from 0.1% to 40% by weight, preferably from 1% to 30% by weight, based on the total weight of the phytosanitary formulation; d) at least one surfactant in an amount of from 0.05% to 40% by weight, preferably from 0.1% to 35% by weight, more preferably from 0.5% to 30% by weight, in particular from 1% to 25% by weight, for example from 1% to 5% by weight, based on the total weight of the phytosanitary formulation; e) optionally water in an amount of from 5% to 90% by weight, preferably from 10% to 80% by weight, in particular from 25% to 70% by weight, based on the total weight of the phytosanitary formulation.

18. The composition according to claim 16 or 17, wherein, The phytosanitary formulation comprises fertilizers, fertilizer stabilizers, fungicides, herbicides, insecticides, acaricides, algicides, molluscicides, acaricides, nematicides, biocides or rodenticides. Use of the compound according to any one of claims 1 to 10 as a solvent, co-solvent and / or crystallization inhibitor or as a coalescing agent.

20. Use according to claim 19, for use in a phytosanitary formulation.

21. Use of the compound according to any one of claims 1 to 10 in a phytosanitary formulation, in particular as a solvent.

22. Use according to claim 19, for use as a solvent for at least one polymer, for coating applications, for manufacturing films, for manufacturing solid-state batteries, for recycling polymers, for preparing polycondensates in solution, or for cleaning equipment, in particular polymerization reactors.

23. Use according to claim 19, for use in household care formulations, for cleaning hard surfaces such as floors, furniture surfaces and surfaces of kitchen and bathroom fittings, or tableware, or in the industrial field for degreasing and / or cleaning the products manufactured.

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