Use of cyclic tertiary amide derivatives as solvents

Abstract

The present invention relates to the use of cyclic tertiary amide derivatives as polar aprotic solvents, e.g. for the solubilization of agricultural active agents in agriculture formulations.

Description

[0001]Use of cyclic tertiary amide derivatives as solvents This application claims priority to the applications filed in Europe on 19.09.2023 with Nr 23306538.2 and on 01.02.2024 with No.24155378.3, the 5 whole content of these applications being incorporated herein by reference for all purposes. TECHNICAL FIELD The present invention relates to the use of cyclic tertiary amide derivatives 10 as polar solvents, e.g. for the solubilization of agricultural active agents in agriculture formulations. TECHNICAL BACKGROUND Industry uses many chemical compounds as solvents, for example for 15 preparing chemicals and materials, for formulating chemical compounds, or for treating surfaces. Solvents are also used for the formulation of agricultural compounds, in particular phytosanitary active agents (fertilizers, pesticides...), for example in the form of emulsifiable concentrates (ECs) intended to be diluted in water by the farmer before being applied to a field. 20 The industry in the field of agriculture attempts to achieve a concentration of the agricultural active compound(s) as high as possible in the respective formulation since a high concentration of the agricultural compound(s) allows the volumes to be applied to be reduced and, as a consequence, entails savings with regard to the adjuvant materials applied and with regard to packaging and 25 logistics. Highly concentrated stable formulations and coformulations with environmentally friendly adjuvants are therefore of interest as a matter of principle. For agricultural active compounds with a low or relatively low water solubility, the use of appropriate solvents is especially interesting to prepare 30 concentrated liquid formulations, in the form of emulsifiable concentrates (EC), concentrated emulsions in water (EW), microemulsions (ME), suspoemulsions (SE), oil dispersions (OD), dispersible concentrates (DC). More details on the definitions of above-mentioned formulations can be found in the “Guidance document for the generation of data on the physical, chemical and technical 35 properties of plant protection products under regulation (EC) N° 1107 / 2009 of the EU parliament and council on placing plant protection products on the market”. Such concentrated formulations of agricultural compounds are generally diluted prior to agricultural use. The dilution effected by the farmer is generally 5 performed by mixing the agrochemical formulation with water. In addition, certain solid agricultural active compounds are often difficult to formulate. For certain agricultural compounds, it is difficult to produce concentrated formulations that are easy for the farmer to dilute, stable and free of substantial drawbacks (real or perceived) with regard to safety, toxicity and / or 10 ecotoxicity. For certain agricultural compounds, it is difficult to formulate at relatively high concentrations with sufficient stability. In particular, it is necessary to avoid the appearance of crystals, in particular at low temperature and / or during dilution and / or during storage of the composition, in particular at low temperature. The crystals may have harmful effects, especially blocking the 15 filters of the devices used for spreading the dilute composition, blocking the spraying devices, reducing the overall activity of the formulation, creating unnecessary problems of waste-management procedures for removing the crystals, and / or causing poor distribution of the agricultural material(s) on the agricultural filed. 20 The agrochemical industry is therefore constantly looking for new solvents and solvent compositions having properties that are satisfactory for agricultural application, like for example, good solubilization efficiency for a wide range of agricultural compounds. In addition, the cost of the solvent compositions should generally be modest, and preferably they should have a favourable toxicology 25 and / or ecotoxicology profile, in particular low toxicity and / or low hazard potential, and / or low volatility (low VOC - volatile organic compounds) and / or advantageously high degree of biodegradability and / or renewability. In the field of emulsifiable concentrate formulations (EC), there is a need for polar solvents that are suitable to solubilize some key active ingredients at 30 high concentrations. N-methyl-2-pyrrolidone (NMP) or N,N-dimethylacetamide are very common polar aprotic solvents that could be used for such application. However, due to their bad toxicological profile they are no longer used, and alternatives are sought. One common polar aprotic solvent that is used is PolarClean which 35 displays a good solubility profile and good toxicity / ecotoxicity profile. However, the agriculture market is now looking for higher performing solvents with clean toxicity / ecotoxicity profiles. Currently, there is only a limited number of commercial options of highly performing solvents with clean toxicity / ecotoxicity profile. Examples for such solvents are N-butylpyrrolidinone (NBP) and N,N- dimethyl lactamide. 5 The three solvents mentioned above (PolarClean, N-butylpyrrolidinone (NBP) and N,N-dimethyl lactamide) are water miscible. The same is true for cyrene. In order to be applied in EC formulations they must be blended with non- water miscible solvents which are usually much less polar in order to avoid crystallization of the active ingredient upon dilution in water and to provide a 10 stable emulsion at the end. An example of such a solvent is Rhodiasolv® ADMA 10. Unfortunately, those non-water miscible solvents are much less efficient for the solubilization of active ingredients resulting in a significantly decreased solubilization efficiency of the final solvent blend. In order to increase the solubility of active ingredients in an EC 15 formulation, two approaches may be followed. Firstly, it is necessary to develop new polar (and water miscible) solvents that show improved solubilization efficiency for a wide range of agricultural active compounds. However, as mentioned, this approach is limited due to the necessary blending with non-water miscible solvents resulting in a significant 20 reduction of the solubility of the active ingredient in the final solvent blend (solubility levelling by the non-water miscible solvent). Therefore, it is also necessary to develop new solvents that are less water miscible or non-water miscible, but still retain some polarity in order to limit the reduction of solubilization efficiency when blended with polar water miscible 25 solvents. It is accordingly the object of the present invention to provide polar solvents that are water miscible and show improved solubilization efficiency for a wide range of agricultural active compounds. It is a further object of the present invention to provide solvents that are not 30 necessarily water miscible but retain some polarity and can be blended with polar, water miscible solvents without compromising on the solubilization efficiency of the resulting solvent blend. SUMMARY OF THE INVENTION 35 In a first aspect, the present invention addresses these objects by using a compound of the following formula (I) 5 wherein R is selected from the group of hydrogen, –(C1-C11)alkyl and –(C3-C11)alkenyl, wherein –(C1-C11)alkyl and –(C3-C11)alkenyl are optionally substituted with a hydroxy group and / or an oxo group, with the proviso that R does not contain a C-C double bond in α,β-position relative to the amide group of 10 the compound of formula (I), as a solvent. It has been found that cyclic tertiary amide derivatives according to formula (I) can be used as polar solvents with advantageous solubilization properties. In particular, it has been found that the compounds of formula (I) show a good ability for solubilization of significant quantities of agricultural active 15 compounds, such as ,e.g., pesticides, and a high compatibility with many agricultural active compounds. By means of the residue R, the solubility properties of the compounds of formula (I) can be tailored. A more hydrophilic residue R enables the provision of a polar solvent that is water miscible and shows improved solubilization 20 efficiency for a wide range of agricultural active compounds. A more hydrophobic residue R enables the provision of a solvent that is less water miscible, but still retains some polarity. Advantageously, the compounds of formula (I) are eco-friendly solvents, which have a good safety and sustainable profile with none or very low hazard 25 classification and none or very low ecotoxicity. In a further aspect, the present invention provides a description for the preparation of a compound of formula (I) as defined above, comprising the step of thermally reacting: a) hexamethyleneimine (HMI), and b) a carboxylic acid R-COOH, wherein R is defined as for the compound of formula (I), 5 wherein "thermally reacting" means that the reaction is carried out at a temperature of at least 100°C. In a further aspect, the present invention provides an agriculture formulation comprising: 10 a) an agricultural active compound, and b) a compound of formula (I); c) optionally at least one co-solvent, d) optionally at least one emulsifier and / or one surfactant, and 15 e) optionally water. Preferred embodiments of the aspects of the present invention are set out in the following description and the appended claims. 20 DETAILED DESCRIPTION OF THE INVENTION The following definitions are relevant in connection with the embodiments of the present invention. The meaning of the term “comprising” is to be interpreted as encompassing all the specifically mentioned features as well optional, additional, unspecified 25 ones, whereas the term “consisting of” only includes those features as specified. Therefore, “comprising” includes as a limiting case the formulation specified by “consisting of”. As used herein, the singular forms "a", "an", and "the" include both singular and plural referents unless the context clearly dictates otherwise. By 30 way of example, "a pesticide" means one pesticide or more than one pesticide. The term “solvent” as used herein denotes a compound that is liquid at the usage temperature, preferably room temperature, and contributes to the solubilisation of a solid substance or to preventing / retarding the solidification or crystallisation of a substance from the solubilized form. The term "room temperature" as used herein refers to a temperature of 20 to 30°C, typically to a temperature of 25°C. The term “(Cx-Cy)alkyl” as used herein denotes in each case a straight- chain or branched alkyl group having from x to y carbon atoms. For example, a (C1-C6)alkyl group includes methyl, ethyl, n-propyl, iso-propyl, n-butyl, 2-butyl, iso-butyl, 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. The term “(Cx-Cy)alkenyl” as used herein denotes in each case a straight- chain or branched alkenyl group having from x to y carbon atoms and comprising at least one C-C double bond. The term “oxo group” as used herein denotes a ketone group, i.e., -(C=O)-. Non-limiting examples of the term “pesticide” comprises insecticides, fungicides, herbicides, acaricides, algicides, molluscicides, rodenticides, nematicides, biocides and miticides. Specific examples of pesticides can be found in the book “Sittig’s handbook of Pesticides and Agricultural Chemicals”, 2ndedition, William Andrew Publishing, 2015. The term “nitrogen fertilizer stabilizer” as used herein refers to an agent that prevents or slow down kinetics of biodegradation of the fertilizer. Non- limiting examples are urease 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 the ammonium ion in fertilizers by inhibiting the activity of Nitrosomonas bacteria in the soil, which transform ammonium into nitrite. Urease inhibitors inhibit the transformation of urea to ammonia and CO2. Fertilizer containing fertilizer stabilizer is often referred to as slow- or controlled-release fertilizer or enhanced efficiency fertilizer (EEF). Non-limiting examples of nitrification inhibitors comprise 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-methyl pyrimidine), ASU (1-amide-2-thiourea), TZ (1H-1,2,4-triazole), 3,4-dimethylpyrazole succinic acid (DMPSA). Non-limiting examples of urease inhibitors comprise NBPT, NPPT and CNPT (cylohexylphosphoric triamide). 5 The term “formulation” as used herein refers to a mixture comprising at least the compound of the invention and another ingredient / compound. This mixture may be homogeneous (i.e. a solution) or heterogeneous (i.e. a dispersion, emulsion, suspension, suspoemulsion). The term “% w / v“ refers to the weight amount of the respective ingredient 10 based on a total volume of the formulation. The embodiments and preferred embodiments according to the invention are further defined hereinafter. The preferred embodiments are preferred alone or in combination. Further, it is to be understood that the following preferred embodiments refer to all aspects of the present invention, i.e. the compound, the 15 method, the formulation as well as the use of the compound. In one aspect, the present invention relates to the use of a compound of formula (I) 20 wherein R is selected from the group of hydrogen, –(C1-C11)alkyl and 25 –(C3-C11)alkenyl, wherein –(C1-C11)alkyl and –(C3-C11)alkenyl are optionally substituted with a hydroxy group and / or an oxo group, with the proviso that R does not contain a C-C double bond in α,β-position relative to the amide group of the compound of formula (I), as a solvent. In a preferred embodiment, R is selected from the group consisting of – 30 (C1-C11)alkyl and –(C3-C11)alkenyl, wherein –(C1-C11)alkyl and –(C3-C11)alkenyl are optionally substituted with a hydroxy (OH) group and / or an oxo group. (C1-C11)alkyl includes C1alkyl (methyl), C2alkyl (ethyl), C3alkyl, C4alkyl, C5 alkyl, C6 alkyl, C7 alkyl, C8 alkyl, C9 alkyl, C10 alkyl, and C11 alkyl, including linear and branched isomers that may optionally be substituted with a hydroxy (OH) group and / or an oxo group. (C3-C11)alkenyl includes C3alkenyl, C4alkenyl, C5alkenyl, C6alkenyl, C7 alkenyl, C8 alkenyl, C9 alkenyl, C10 alkenyl, C11 alkenyl, including linear and branched isomers that may optionally be substituted with a hydroxy (OH) group and / or an oxo group. It is preferred that –(C1-C11)alkyl and –(C3-C11)alkenyl are linear residues. In a further preferred embodiment, R is selected from the group consisting of hydrogen, -CH3, -C2H5, n-C3H7, n-C4H9, n-C5H11, n-C6H13, n- C7H15, n-C8H17, n-C9H19, n-C10H21 and n-C11H23, which may optionally be substituted with a hydroxy (OH) group and / or an oxo group. In a more preferred embodiment, R is selected from the group consisting of hydrogen, -CH3, -(OH)CH-CH3, n-C3H7, n-C5H11,CH3-C(=O)-CH2-CH2- and n-C9H19. Particularly preferred for the inventive use are compounds wherein R is - CH3, -(OH)CH-CH3 or n-C3H7. The compounds wherein R is -CH3 or n-C3H7 correspond to compound Ia and Ib prepared in Examples 1 and 2, respectively, and they give particularly good results. The compounds wherein R = -(OH)CH- CH3 and R = -CH2-CH2-(C=O)-CH3 correspond to compounds Ic and Id in examples 3 and 4 respectively. Those compounds are partially bio-based as they are manufactured from lactic acid and levulinic acid respectively. Depending on residue R, the compounds according to formula (I) display very differentiating solubility performances for a wide range of agricultural active compounds. The solubility performance of the compound can be tailored by means of the residue R. In general, a short-chained and / or more polar residue R, such as e.g. -(OH)CH-CH3, will increase the water miscibility of the compound of formula (I), whereas water miscibility will decrease with a more hydrophobic residue R. For example, compound Ia prepared in Example 1, wherein R = -CH3 and compound Ic prepared in example 3 wherein R = - (OH)CH-CH3are water miscible, whereas compound Ib prepared in Example 2, wherein R = n-C3H7 has a water miscibility of only 5 wt-%. It is interesting to note that compound Ia prepared in Example 1 in fact has the same chemical formula as the known solvent N-butylpyrrolidinone 5 (NBP) (C8H15NO). Surprisingly, compound Ia displays higher solubilization performance compared to NBP showing that the peculiar cyclic structure of compound Ia advantageously influences the solubilization efficiency of the compound. 10 The inventive use of the compound of formula (I) as solvent also includes the use as a co-solvent and / or as a crystallization inhibitor. The use as a co- solvent implies that the compound of formula (I) is used in combination with at least one further solvent. This at least one further solvent can be a solvent in accordance with the compound of formula (I) or a solvent that is not in 15 accordance with the compound of formula (I). The compounds of formula (I) also act as crystallization inhibitors, for example in emulsifiable concentrates, wherein the agricultural active compound is present in highly concentrated form before the concentrate is diluted in water by the farmer for its application to a field. 20 The compounds of formula (I) advantageously not only show good to excellent solubilization properties, but have preferably very good safety and sustainable profiles, with none or very low hazard classification and none or very low ecotoxicity. For example, the compound of formula Ia prepared in example 1 25 shows a good biodegradability profile achieving 100% biodegradability rate after 28 days in an inherent biodegradability OECD302B assay. This is a significant environmental benefit. For comparison, public data from Echa shows that the isomeric commercial product NBP displays only 7% of biodegradability rate after 28 days. 30 Compounds of formula (I) may therefore generally be used as a replacement for toxic solvents such as N-methyl-2-pyrrolidone (NMP) or as a replacement for other polar and eco-friendly solvents, such as NBP (N-butyl-2- pyrrolidone), Rhodiasolv® PolarClean, N,N-dimethyl lactamide and Rhodiasolv® ADMA 10. The cyclic tertiary amide derivatives according to formula (I) can be 5 obtained in a single amidification step using a well-chosen carboxylic acid and a 7-membered cyclic secondary amine. For this purpose, the present invention provides a process for the preparation of a compound of formula (I) comprising the step of thermally reacting 10 a) hexamethyleneimine (HMI), and b) a carboxylic acid R-COOH, wherein R is as defined for the compound of formula (I), wherein "thermally reacting" means that the reaction is carried out at a 15 temperature of at least 100°C. Preferably, hexamethyleneimine (HMI) is added to the carboxylic acid R- COOH or vice versa, depending on the boiling point of the carboxylic acid, over a defined period of time, such as e.g.0.5 to 5 hrs, preferably 0.5 to 1 hrs. Preferably, the process is carried out at a temperature between 100°C and 20 250°C, such as e.g.120 to 180°C. Preferably, the process is carried out in the absence of an additional solvent. Preferably, water by-product is removed during the reaction in order to shift the reaction equilibrium towards the amide product, i.e. the compound of formula (I). Water distillation during the course of the reaction increases 25 conversion and product yield. Water can be removed from the reaction mixture by e.g. distillation. Preferably the process is carried out at atmospheric pressure but vacuum can also be applied in order to assist water removal. The reaction can be carried out at a pressure ranging from 10 mbar to 1 atm. 30 Using a carboxylic acid allows to significantly reduce production costs compared to acid derivatives which are more expensive raw materials and which are generally produced from these carboxylic acids. Acid derivatives are generally more reactive and therefore have a poorer HSE profile than the acids from which they are derived (for example acetyl chloride compared to acetic acid). Besides, carboxylic acids are also much more industrially available than 5 carboxylic acid derivatives especially when it comes to large volumes. Finally, in terms of environmental footprint the direct condensation of an amine with an acid to form an amide has a better atom economy and only generates water as a by-product unlike the condensation of amines with acid derivatives where salts are co-produced as waste that must therefore be treated. 10 In a further aspect, the present invention relates to an agriculture formulation (or agrochemical formulation) comprising an agricultural active compound and a compound of formula (I), wherein agriculture active compounds as described above can be used. The agriculture formulation of the present invention may comprise: 15 a) at least one agricultural active compound (in particular only one agricultural active compound, or a combination of different agricultural active compounds); b) the compound of formula (I) used as a solvent or co-solvent; c) optionally at least one emulsifier or / and one surfactant; and 20 d) optionally water. As used herein, the term “agricultural active compound” means an active ingredient used in particular to the practice of farming, including cultivation of the soil for the growing of crops. However, the use of agricultural active 25 compounds is not limited to application to crops. Agricultural active compounds (or materials) may be applied to any surface, e.g., for the purpose of cleaning or aiding or inhibiting growth of a living organism. Other non-crop applications include, but are not limited to, application to turf and ornamentals, and application to railroad weed. 30 The agricultural active compounds are generally products in pure or highly concentrated form. The agricultural active compound suitable for use in the present invention is preferable selected from the group consisting of pesticides, biopesticides, fertilizers, fertilizer stabilizers, nutrients, biostimulants, plant growth regulators, natural plant defense enhancers, inoculants and mixtures thereof. 5 Pesticides suitable for use in the present invention include herbicides, insecticides, acaricides, fungicides, algicides, molluscicides, miticides, nematicides, biocides and rodenticides as well as mixtures thereof. Non-limiting examples of fungicides suitable for use in the present invention include azoles such as e.g. prothioconazole, epoxiconazole, 10 difenoconazole, propiconazole, cyproconazole, tebuconazole; strobilurins such as e.g. azoxystrobin, trifloxystrobin, picoxystrobin, fluoxastrobin, pyraclostrobin; and succinate dehydrogenase inhibitors (SDHIs) (carboxamides) such as bixafen, fluxapyroxad, benzovindiflupyr, fluopyram; and mixtures thereof. The agricultural active compounds can be water-insoluble, at 20°C and at 15 atmospheric pressure (i.e., 1.013x105Pa). In particular, the agricultural active compounds can be soluble in water to no more than 100 g / L, generally no more than 20 g / L, notably no more than 5 g / L, for instance no more than 1 g / L and even no more than 0.2 g / L, at 20°C and at atmospheric pressure (i.e., 1.013x105Pa). 20 In a further embodiment, the agriculture formulation is a fertilizer formulation, preferably an enhanced efficiency fertilizer formulation, which comprises a fertilizer and / or a fertilizer stabilizer, in particular a nitrogen fertilizer and / or a nitrogen fertilizer stabilizer and / or a urease and / or nitrification 25 inhibitor. The fertilizer and / or a fertilizer stabilizer, in particular the nitrogen fertilizer and / or nitrogen fertilizer stabilizer and / or urease and / or nitrification inhibitor may be N-(n-butyl)thiophosphoric acid triamide (NBPT) and / or dicyandiamide (DCD). 30 In another embodiment, said fertilizer formulation further comprises at least one biostimulant, one plant growth regulator, one natural plant defense enhancer and / or one inoculant. In another embodiment, said fertilizer formulation further comprises at least one pesticide, for example an herbicide, an insecticide, a fungicide, an acaricide, an algicide, a molluscicide, a miticide, a nematicide, a biocide or a rodenticide, for instance a raticide. 5 The present invention gives particularly good results with pesticides, particularly with fungicides, in particular with a fungicide selected from azoles, strobilurins and carboxamides; and mixtures thereof. Generally, the amount of agricultural active compound(s) in the agriculture formulation of the invention ranges from 0.01 to 90% by weight, 10 preferentially from 0.1 to 90% by weight more preferentially from 0.1 to 80% by weight; even more preferentially from 0.5 to 70% by weight; better from 1 to 65% by weight, in particular from 5 to 60% by weight, and for instance from 10 to 60% by weight, relative to the total weight of the agriculture formulation. According to a particular embodiment of the invention (concentrated 15 formulation), the total content of agricultural active compound(s) in the agriculture formulation ranges from 5 to 90% by weight, preferentially from 5 to 70% by weight, more preferentially from 5 to 60% by weight, and in particular from 10 to 60% by weight, relative to the total weight of the agriculture formulation. 20 According to another particular embodiment of the invention (diluted formulation), the total content of agricultural active compound(s) in the agriculture formulation ranges from 0.01 to 3% by weight, preferentially from 0.05 to 2% by weight, and more preferentially from 0.1 to 1% by weight, relative to the total weight of the agriculture formulation. 25 Generally, the compound of formula (I) represents from 10 to 99.9% by weight, preferentially from 10 to 99% by weight, more preferentially from 20% to 95% by weight, in particular from 30% to 90% by weight, for instance from 30% to 80% by weight, relative to the total weight of the agrochemical formulation. 30 It is possible to combine several agricultural active compounds in the agriculture formulation of the invention. The agriculture formulation according to the invention may comprise at least one biostimulant. The term “biostimulant” is preferably intended to mean a compound which may enhance metabolic or physiological processes such as respiration, 5 photosynthesis, nucleic acid uptake, ion uptake, nutrient delivery, or a combination thereof. Generally, this is a substance or microorganism that, when applied to seeds, plants or on the rhizosphere, can stimulate natural processes to enhance or benefit nutrient uptake, nutrient use efficiency, tolerance to abiotic stress, or crop 10 quality and yield. Non-limiting examples of biostimulants include seaweed extracts (e.g., ascophyllum nodosum), humic acids (e.g., potassium humate), fulvic acids, myoinositol, glycine, and combinations thereof. 15 The agricultural formulation according to the invention may comprise at least one plant growth regulator. Plant growth regulators mean active ingredients used to influence the growth characteristics of plants. Examples of plant growth regulators which may be used in the present invention include, but are not limited to: 1-20 naphthaleneacetic acid, 1-naphthaleneacetic acid -salt, 1-napthol, 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, 2-naphthoxyacetic acid sodium salt, 3-chloro-4-hydroxyphenylacetic acid, 3-indoleacetic acid, 4- biphenylacetic acid, 4-chlorophenoxyacetic acid (4-CPA), 4- 25 hydroxyphenylacetic acid, 6-benzylaminopurine, auxindole, a-naphthaleneacetic acid K-salt, ß-naphfhoxyacetic acid, p-chlorophenoxyacetic acid, dicamba, dichlorprop, 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, 30 indole-3 -propionic acid; a-naphthaleneacetic acid, methyl indole- 3 -acetate, naphthaleneacetamide, naphthaleneacetic acid (NAA), phenylacetic acid, picloram, potassium naphthenate, sodium naphthenate, 4-hydroxyphenethyl alcohol, 4-CPPU, 6-benzylaminopurine (BA), 6-(Y,Y-dimethylallylamino)purine (2iP), 2-iP- 2HC1, adenine, adenine hemisulfate, benzyladenine, kinetin, meta- topolin, N6- benzoyladenine, N- benzyl-9-(2-tetrahydropyranyl) adenine (BP A), N-(2-chloro-4- pyridyl)-N-phenylurea, gibberellic acid (GA3), gibberellins, 5 gibberellins A4 + A7 (GA n), ethylene and abscisic acid. The agriculture formulation according to the invention may optionally comprise at least one emulsifier. Emulsifiers are agents that are intended to facilitate emulsification after 10 the formulation is placed in the presence of water, and / or stabilisation (over time and / or in temperature) of the emulsion, for example by avoiding separation of the phases. Generally, the total amount of emulsifier(s) in the agriculture formulation according to the invention, ranges from 0.05 to 40% by weight, preferentially 15 from 0.1 to 35% by weight, more preferentially from 0.5 to 30% by weight, in particular from 1 to 25% by weight, for instance from 1 to 5% by weight, relative to the total weight of the agriculture formulation. Generally, the agrochemical formulation according to the invention 20 further comprises at least one surfactant. Advantageously, the surfactants that may be used in the invention are chosen from anionic, non-ionic, cationic, amphoteric or zwitterionic surfactants, and mixtures thereof. Preferentially, the surfactants are chosen from anionic surfactants, non- 25 ionic surfactants, and mixtures thereof. More preferentially, the surfactants are chosen from anionic surfactants, polyalkoxylated non-ionic surfactants, and mixtures thereof. The emulsifiers and surfactants that may be used are different from the agricultural active compound(s). 30 By way of examples of anionic surfactants, mention may be made without any intended limitation thereto, of: - alkylsulfonic acids, arylsulfonic acids, optionally substituted with one or more hydrocarbon groups, and the acid function of which is partly or totally salified, like C8-C50alkylsulfonic acids, more particularly C8-C30, preferably C10- C22 alkylsulfonic acids, benzenesulfonic acids, naphthalenesulfonic acids, substituted with one to three C1-C30, preferably C4-C16alkyl and / or C2-C30, preferably C4-C16 alkenyl groups, - mono- or di-esters of sulfosuccinic acids, of which the linear or branched alkyl portion is optionally substituted with one or more linear or branched C2-C4 hydroxylated and / or alkoxylated (preferably ethoxylated, propoxylated, ethopropoxylated) groups, - phosphate esters more particularly selected from among those comprising at least one linear or branched, saturated, unsaturated or aromatic hydrocarbon group, comprising 8 to 40 carbon atoms, preferably 10 to 30, optionally substituted with at least one alkoxylated (ethoxylated, propoxylated, ethopropoxylated) group. In addition, they comprise at least one phosphate ester group, mono- or di-esterified such that it is possible to have one or two free or partly or totally salified groups. The preferred phosphate esters are of the type of the mono- and di-esters of phosphoric acid and of alkoxylated (ethoxylated and / or propoxylated) mono-, di- or tri-styrylphenol, or alkoxylated (ethoxylated and / or propoxylated) mono-, di- or trialkylphenol, optionally substituted with one to four alkyl groups; of phosphoric acid and of an alkoxylated (ethoxylated or propoxylated) C8-C30, preferably C10-C22 alcohol; of phosphoric acid and of a non-alkoxylated C8-C22, preferably C10-C22 alcohol, - sulfate esters obtained from saturated or unsaturated or aromatic alcohols optionally substituted with one or more alkoxylated (ethoxylated, propoxylated, ethopropoxylated) groups, and for which the sulfate functions appear in the free acid form, or are partly or totally neutralised. As an example, mention may be made of sulfate esters more particularly obtained from saturated or unsaturated C8-C20alcohols, which may comprise 1 to 8 alkoxylated (ethoxylated, propoxylated, ethopropoxylated) units ; sulfate esters obtained from polyalkoxylated phenol, substituted with 1 to 3 saturated or unsaturated C2- C30 hydrocarbon groups, and in which the number of alkoxylated units is comprised between 2 and 40 ; the sulfate esters obtained from polyalkoxylated mono-, di- or tri-styrylphenol in which the number of alkoxylated units varies from 2 to 40. The anionic surfactants may be in the acid form (they are potentially anionic), or in a partly or totally salified form with one counter-ion. The counter- ion may be an alkali metal, such as sodium or potassium, an alkaline earth metal, such as calcium, or moreover even an ammonium ion of formula N(R)4+in which the R groups, either identical or different, represent a hydrogen atom or a C1-C4 alkyl group optionally substituted with an oxygen atom. By way of examples of non-ionic surfactants, mention may be made without any intended limitation thereto, of: - polyalkoxylated (ethoxylated, propoxylated, ethopropoxylated) phenols substituted with at least one C4-C20, preferably C4-C12 alkyl group, or substituted with at least one alkylaryl group, the alkyl portion of which is a C1-C6alkyl. More particularly, the total number of alkloxylated units is comprised between 2 and 100. As an example, mention may be made of polyalkoxylated mono-, di- or tri-(phenylethyl) phenols, or polyalkoxylated nonylphenols. Amongst the ethoxylated and / or propoxylated, sulfated and / or phosphated di- or tri- styrylphenols, 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 ; phosphated ethoxylated tri-(phenyl-1-ethyl) phenol containing 16 oxyethylene units. - polyalkoxylated (ethoxylated, propoxylated, ethopropoxylated) C6- C22fatty acids or alcohols. The number of alkoxylated units is comprised between 1 and 60. The term ethoxylated fatty acid includes both the products obtained by ethoxylation of a fatty acid by ethylene oxide as well as those obtained by esterification of a fatty acid by a polyethylene glycol. - polyalkoxylated (ethoxylated, propoxylated, ethopropoxylated) triglycerides of vegetable or animal origin. Thus, may be included triglycerides from lard, tallow, ground nut oil, butter oil, cotton seed oil, flax oil, olive oil, palm oil, grapeseed oil, fish oil, soya bean oil, castor oil, rapeseed oil, coprah oil, 5 coconut oil, and comprising a total number of alkoxylated units comprised between 1 and 60. The term ethoxylated triglyceride makes reference both to products obtained by ethoxylation of a triglyceride with ethylene oxide as well as to those obtained by transesterification of a triglyceride with a polyethylene glycol. 10 - sorbitan esters, optionally polyalkoxylated (ethoxylated, propoxylated, ethopropoxylated), more particularly the cyclised sorbitol esters of C10-C20 fatty acids such as lauric acid, stearic acid, or oleic acid, and comprising a total number of alkoxylated units comprised between 2 and 50. Useful emulsifiers are in particular the following products, all marketed 15 by the Applicant: - Soprophor® TSP / 724: a surfactant based on ethopropoxylated tristyrylphenol, - Soprophor® 796 / P: a surfactant based on ethopropoxylated tristyrylphenol, 20 - Soprophor® CY 8: a surfactant based on ethoxylated tristyrylphenol, - Soprophor® BSU: a surfactant based on ethoxylated tristyrylphenol, - Soprophor® S / 25: a surfactant based on ethoxylated tristyrylphenol, - Soprophor® 3D33: a surfactant based on ethoxylated tristyrylphenol, phosphate ester, 25 - Alkamuls® RC: a surfactant based on ethoxylated castor oil, - Alkamuls® OR / 36: a surfactant based on ethoxylated castor oil, - Alkamuls® VO2003: a surfactant based on ethoxylated castor oil, - Alkamuls® OL40: a surfactant based on ethoxylated sorbitan hexaoleate, 30 - Alkamuls® T / 20: a surfactant based on ethoxylated sorbitan ester. - Geronol® TBE724: a surfactant based on ethopropoxylated tristyrylphenol, - Geronol® TEB25: a mixture of surfactants based on ethoxylated castor oil, calcium dodecyl benzene sulfonate and alkoxylated polymers, - Rhodacal® 60 / B: a surfactant based on dodecylbenzene sulphonate, - Rhodacal® 60 / BE: a surfactant based on dodecylbenzene sulphonate. 5 Generally, the total amount of surfactant(s) in the agriculture formulation according to the invention, ranges from 0.05 to 40% by weight, preferentially from 0.1 to 35% by weight, more preferentially from 0.5 to 30% by weight, in particular from 1 to 25% by weight, for instance from 1 to 5% by weight, relative to the total weight of the agriculture formulation. 10 Generally, the total amount of anionic surfactant(s) in the agriculture formulation according to the invention, ranges from 0.05 to 40% by weight, preferentially from 0.1 to 35% by weight, more preferentially from 0.5 to 30% by weight, in particular from 1 to 25% by weight, for instance from 1 to 5% by weight, relative to the total weight of the agriculture formulation. 15 Generally, the total amount of non-ionic surfactant(s), in particular polyalkoxylated non-ionic surfactant(s) in the agriculture formulation according to the invention, ranges from 0.05 to 40% by weight, preferentially from 0.1 to 35% by weight, more preferentially from 0.5 to 30% by weight, in particular from 1 to 25% by weight, for instance from 1 to 5% by weight, relative to the 20 total weight of the agriculture formulation. The agriculture formulation according to the invention may further comprise at least one co-solvent, different from the compound of formula (I). This other solvent or co-solvent can generally be selected from: 25 - linear or branched, saturated or unsaturated, aliphatic hydrocarbons, possibly containing a halogen -, phosphorus -, sulfur - and / or nitrogen atom and / or a functional group, - carbocyclic or heterocyclic hydrocarbons, whether saturated, unsaturated or aromatic, possibly containing a halogen -, phosphorus -, sulfur - 30 and / or nitrogen atom and / or a functional group, More particularly, this co-solvent is chosen from: - alkanes, cycloalkanes and aromatic derivatives, for example paraffins with a branched chain or straight chain such as "white oil" or decalin; mono-, di- or tri alkyl benzenes or naphthalenes, the compounds sold under the name Solvesso® 100, 150, 200 standard and ND grades; 5 - aliphatic, cycloaliphatic or aromatic mono-, di- or tri-esters, for example alkyl alkanoates such as methyl oleate ; benzyl alkanoates; alkyl benzoates; gamma butyrolactone; caprolactone ; esters of glycerol and citric acid ; alkyl salicylates; phthalates; dibenzoates; acetoacetates; glycol ether acetates, dipropylene glycol diacetate; lactates; fumarates, succinates, adipates, maleates; 10 levulinates. - alkyl mono-, di-, or tri-phosphates such as for example triethyl phosphate; tributyl phosphate; or tri-2-ethylhexylphosphate; - aliphatic, cycloaliphatic or aromatic ketones such as for example dialkyl 15 ketones; benzyl ketones; fenchone; acetophenone; cyclohexanone; alkyl cyclohexanones; isophorone; cyclopentanone. - aliphatic, cycloaliphatic or aromatic alcohols such as for example glycols; 2-ethylhexanol; cyclohexanol; benzyl alcohols; tetrahydrofurfuryl alcohol; 20 - aliphatic, cycloaliphatic or aromatic ethers such as for example ethers of glycol, notably ethylene and propylene glycol, and their polymers; diphenyl ether, dipropylene glycol ; monomethyl or monobutyl ether, monobutyl ether of tripropylene glycol; alkoxyalkanols; dimethyl isosorbide; - fatty acids such as for example linoleic acid, linolenic acid, oleic acid; 25 - carbonates such as for example propylene or butylene carbonate; - amides such as for example alkyldimethylamides, dimethyl- decanoamide; N-alkyl-pyrrolidones; dimethyl lactamide. - alkyl ureas; - amines such as for example alkanolamines, morpholine ; 30 - tetramethyl sulfone; sulfolane; - dimethyl sulfoxide; - halogenoalkanes or halogenated aromatic solvents such as for example chloroalkanes or chlorobenzene. Crystallisation inhibitors may also be present in the agriculture 5 formulations according to the invention. Crystallisation inhibitors may be the co- solvents mentioned here above. Crystallisation inhibitors may also be non- polyalkoxylated fatty alcohols or fatty acids, for example mention may be made of the product Alkamuls® OL700 marketed by the Applicant, alkanolamides, polymers. 10 The agriculture formulation according to the invention may further contains one or more additives different from the ingredients described previously, and which are preferably chosen from viscosity modifying agents, suspending agents, antifoam agents and defoamers, in particular silicone 15 antifoams and defoamers, anti-rebound agents, anti-leaching agents, penetration adjuvants, inert fillers, in particular mineral fillers, binders, diluents, anti-freeze agents, stabilisers, dyes, emetic agents, stickers (adhesion promoters), absorbents, dispersants, disintegration agents, wetting agents, preservatives and / or anti-microbials. 20 Each additive can be present in the agriculture formulation according to the invention in an amount ranging from 0 to 20% by weight, preferably from 0 to 10% by weight, relative to the total weight of the agriculture formulation. Each additive can be for instance present in the agricultural formulation according to the invention in an amount ranging from 0.1 to 20% by weight, in 25 particular from 0.1 to 10% by weight, relative to the total weight of the formulation. Each additive can be present in the agrochemical formulation according to the invention in an amount preferably ranging from 0 to 5% by weight, notably from 0.1 to 5% by weight, relative to the total weight of the formulation. A person skilled in the art will be able to choose these optional 30 additives and their amounts so that they do not harm the properties of the agriculture formulation of the present invention. Advantageously, the agriculture formulation according to the invention is in a liquid form, at 20°C and at atmospheric pressure (i.e., 1.013x105Pa) and may be in the form of a concentrate of agricultural active compound(s), a diluted concentrate, or a sprayable diluted. 5 Different types of formulation may be used according to the different agricultural active compound(s). The formulations that it is possible to use depend on the physical form of the agricultural active materials (for example solid or liquid) and on their physicochemical properties in the presence of other compounds such as water or solvents. 10 For practical reasons (for example for reasons of ease of handling), it may be preferred to use formulations in liquid form. Depending on the physicochemical properties of the different agricultural active compound(s) considered, formulations can be in the form of emulsifiable concentrates (EC), concentrated emulsions in water (EW), microemulsions (ME), suspoemulsions 15 (SE), oil dispersions (OD), dispersible concentrates (DC), suspension concentrates (SC), capsule suspensions (CS), soluble liquids (SL), flowable concentrates for seed treatments (FS). Preferably, the agriculture formulation according to the invention is in the form of an emulsifiable concentrate (EC), concentrated emulsion in water (EW), 20 microemulsion (ME), suspoemulsion (SE), oil dispersion (OD), dispersible concentrate (DC), capsule suspension (CS), soluble liquid (SL). More preferentially, the agriculture formulation according to the invention is in the form of an emulsifiable concentrate, an emulsion in water concentrate, a microemulsion concentrate, a suspoemulsion concentrate, an oil 25 dispersion concentrate or a dispersible concentrate. In a particular embodiment, the agriculture formulation according to the invention is in the form of an emulsifiable concentrate (EC). The agriculture formulation according to the invention is generally a 30 concentrated agrochemical formulation and is intended to be spread out over a cultivated field or a field to be cultivated, most often after dilution with water, in order to obtain a diluted formulation. Dilution is generally carried out by the farm operator, directly in a tank (“tank-mix”), for example in the tank of a device intended to spread out the formulation. This does not exclude the possibility of the farm operator adding other plant-protective products, for example fungicides, herbicides, pesticides, insecticides, fertilisers, adjuvants, etc. Thus, the 5 formulation may be used for preparing a formulation diluted in water of the agricultural active compound(s), by mixing at least one part by weight of concentrated formulation with at least 10 parts of water, preferably less than 10,000 parts. The dilution ratios and the amounts to be applied over the field generally depend on the agricultural active compound(s) and on the desirable 10 dose for treating the field (this may be determined by the farm operator). According to one embodiment of the invention, the agrochemical formulation according to the invention is aqueous. According to this embodiment, the water content of the agriculture 15 formulation preferably ranges from 5 to 99% by weight, more preferentially from 20 to 95% by weight, even more preferentially from 25 to 90% by weight, in particular from 25 to 85% by weight, for instance from 25 to 70% by weight, relative to the total weight of the agriculture formulation. According to this embodiment, the pH preferably ranges from 1 to 11, 20 and particularly from 2.5 to 9.5. The pH of the formulations can be adjusted to the desired value by means of basifying agents or acidifying agents. Use may be made, among the basifying agents, of one or more alkaline agents, such as ammonia, sodium hydroxide or ethanolamine. Mention may be made, by way of examples, among the acidifying 25 agents, of inorganic or organic acids, such as hydrochloric acid or orthophosphoric acid. According to a particular embodiment of the invention, the agriculture formulation may advantageously comprise: 30 a) from 0.01 to 90% by weight, preferably from 5 to 60% by weight, of at least one agricultural active compound (only one agricultural active compound or a combination of different agricultural active compounds), preferably at least one pesticide, relative to the total weight of the agriculture formulation, b) from 5 to 90% by weight, preferably from 10 to 90% by weight, in particular from 30 to 90% by weight, for instance from 30 to 80% by weight, of a 5 compound of the invention or of a mixture of compounds according to the present invention, relative to the total weight of the agriculture formulation, c) from 0.1 to 40% by weight, preferably from 1 to 30% by weight, of at least one said co-solvent, relative to the total weight of the agriculture formulation, 10 d) from 0.05 to 40% by weight, preferably from 0.1 to 35% by weight, more preferentially from 0.5 to 30% by weight, in particular from 1 to 25% by weight, for instance from 1 to 5% by weight, of at least one surfactant, relative to the total weight of the agriculture formulation, e) from 5 to 90% by weight, preferably from 10 to 80% by weight, in 15 particular from 25 to 70% by weight, of water, relative to the total weight of the agriculture formulation. Known conventional methods for preparing agriculture formulations may be implemented. It is possible to undertake this by simply mixing the constituents. 20 The agriculture formulation according to the invention may be used to kill or inhibit pests and / or clean and / or inhibit growth of undesired plants. The agriculture formulation according to the invention can be diluted and applied to at least one plant, area adjacent to a plant, soil adapted to support growth of a plant, root of a plant, foliage of a plant, and / or seed adapted to 25 produce a plant, in a customary manner; for example by watering (drenching), drip irrigation, spraying, and / or atomizing. Besides their use as solvents, co-solvents and / or crystallization inhibitors, particularly in agriculture formulations, the compounds of formula (I) are also 30 useful for coating applications, the manufacturing of membranes, or solid batteries. The compounds of formula (I) can furthermore be used in recycling processes of polymers, especially chemically resistant polymers like PVDF or PVDC (polyvinylidene chloride), still as a replacement of polar solvents such as NMP, DMF, DMSO, acetophenone and DMAc. 5 The compounds of formula (I) can also be used for the preparation, in solution, of polycondensates, especially polyimides or polyesters or polyamides or polyamide-imides, especially partially or completely aromatic polycondensates such as aromatic polyamides (aramids). Moreover, the compounds of formula (I) can be used as cleaning solvent 10 for the cleaning of equipment like reactors for instance, in particular polymerization reactors. Since the compounds of formula (I) are advantageously eco-friendly solvents and have preferably good safety and sustainable profiles, they can also advantageously be used as solvents in household care formulations, used in 15 homes or in public areas (hotels, offices, factories, etc.). They may be formulated for cleaning hard surfaces such as floors, the surfaces of furniture and of kitchen and bathroom fittings, or dishes. These formulations may also be used in the industrial sphere for degreasing manufactured products and / or for cleaning them. Should the disclosure of any patents, patent applications, and publications 20 which are incorporated herein by reference conflict with the description of the present application to the extent that it may render a term unclear, the present description shall take precedence. EXAMPLES 25 Example 1: Synthesis of compound Ia (R = -CH3) The reaction was conducted under an inert argon atmosphere. In a 1L double-jacket reactor equipped with a mechanical stirrer (3 inclined blades) and baffles, a temperature probe recording the temperature 30 inside the reaction mass, a condenser (5°C), another temperature probe recording the temperature at the condenser bottom and a short path distillation apparatus connected to a collector were added at room temperature: 253.4 g HMI (2.55 moles, 1.1 eq.). The reaction mass was allowed to stir at 140°C, 400 rpm. The short path distillation valve was closed to put the system in total reflux configuration. Acetic acid (137.8 g, 2.30 moles, 1 eq.) was progressively added into the reactor over a period of 4 hrs. Following the addition of acetic acid, a reflux was observed (around 100°C measured at the bottom of the condenser). At the end of acetic acid addition,1H NMR analysis showed that the conversion level was limited at around 12 mol%. The short path distillation valve was opened in order to distil out the water and to shift the equilibrium toward the formation of the desired amide. During this water distillation phase, the temperature of the reaction mass was progressively increased to 180°C and after 3 hrs at 160-180°C,1H NMR analysis showed a conversion level of 94 mol%. The amide product was then purified by vacuum distillation at 160°C (reaction mass temperature) and 100-70 mbar vacuum. The following intermediate fractions were recovered and could be recycled in another batch: - 1stfraction (b.p.140°C, 90 mbar, 7.68g): [AcOH: 2.5 g, HMI: 1.4 g, product: 3.9 g] - 2ndfraction (b.p.145-155°C, 90 mbar, 18.4g):[AcOH: 4.2 g, HMI: 0.5 g, product: 13.7 g] - 3rdfraction (b.p.155°C, 72 mbar, 54.3 g): [AcOH: 1 g, product: 53.3 g] The pure product was recovered in a 4thfraction (b.p.: 151°C, 68 mbar): 222.9 g, corresponding to an isolated yield of 69%: Acid Value: 1.58 mg(KOH) / g Karl Fischer.: 0.05 wt% (H2O). 1H NMR (CDCl3, 400 MHz) δ (ppm): 3.45 (t, J = 6.4 Hz, 2H), 3.35 (t, J = 6.0 Hz, 2H), 2.02 (s, 3H), 1.74-1.60 (m, 4H), 1.58-1.46 (m, 4H). 13C (CDCl3, 101 MHz) δ (ppm): 169.84, 48.43, 45.42, 28.75, 27.31, 26.80, 26.62, 21.32. Example 2: Synthesis of a compound Ib (R = -CH2-CH2-CH3) The reaction was conducted under an inert argon atmosphere. In a 1L double-jacket reactor equipped with a mechanical stirrer (3 inclined blades) and baffles, a temperature probe recording the temperature inside the reaction mass, a condenser (5°C), another temperature probe recording the temperature at the condenser bottom and a short path distillation apparatus connected to a collector were added at room temperature: 200.47 g of butanoic acid (2.28 moles, 1.2 eq.). The reaction mass was allowed to stir at 160°C (400 rpm) and the short path distillation valve was closed to put the system in total reflux configuration. HMI (192.47 g, 1.94 moles, 1 eq.) was progressively added into the reactor over a period of 4 hrs. During the addition of HMI, a reflux was being formed (around 100°C measured at the bottom of the condenser) associated with a decrease of the reaction mass temperature (from 160°C to 140°C). At the end of HMI addition,1H NMR analysis showed that the conversion level was limited at around 26 mol%. The short path distillation valve was opened in order to distil out the water and to displace the equilibrium toward the formation of the desired amide. During this water distillation phase, the temperature of the reaction mass was increased to 170°C and after 3 hrs at 170°C,1H NMR analysis showed a conversion level of 85 mol%. The amide product was then purified by vacuum distillation at 16 mbar vacuum with reaction mass temperature increasing from 120°C to 145°C. The following intermediate fractions were recovered and could be recycled in another batch: - 1stfraction (b.p.92°C, 16 mbar, 6.1g): [Butanoic: 5.7 g, HMI: 0.1 g, product: 0.3 g] - 2ndfraction (b.p.108°C, 16 mbar, 3.2g): [Butanoic: 2.7 g, HMI: 0.1 g, product: 0.4 g] - 3rdfraction (b.p.116°C, 16 mbar, 28 g): [Butanoic: 14.1 g, HMI: 3.3 g, product: 10.6 g] - 4thfraction (b.p.120°C, 16 mbar, 30.0 g): [Butanoic: 13.7 g, HMI: 1.7 g, product: 14.6 g] The crude product was recovered in a 5thfraction (b.p.: 132°C, 16 mbar): 265.08 g. At this stage the crude product still contained a residual amount of butanoic acid (~ 4.6 g) and was therefore purified through washing with 200 mL of saturated aqueous NaHCO3 followed by washing with 200 mL of saturated aqueous NaCl. The product was finally dried under vacuum (95°C, 15 mbar) followed by a cleaning filtration to afford 227.72 g of the product, corresponding to an isolated yield of 69%. Acid value: 5.62 mg(KOH) / g Karl Fischer: 0.12 wt% (H2O). 1H NMR (CDCl3, 400 MHz) δ (ppm): 3.54 (t, J = 6.4 Hz, 2H), 3.45 (t, J = 6.0 Hz, 2H), 2.31 (t, J = 7.2 Hz, 2H), 1.80-1.50 (m, 10H), 0.99 (t, J = 7.2 Hz, 3H). 13C (CDCl3, 101 MHz) δ (ppm): 171.8, 47.3, 45.2, 34.6, 28.6, 27.1, 26.5, 26.2, 18.2, 13.4. Exemple 3: Synthesis of a compound Ic (R = -(OH)CH-CH3) The reaction was conducted under an inert argon atmosphere. In a 1L double-jacket reactor equipped with a mechanical stirrer (4 inclined blades) and baffles, a temperature probe recording the temperature inside the reaction mass, a condenser (10°C), another temperature probe recording the temperature at the condenser bottom and a short path distillation apparatus connected to a collector were added at room temperature: 250 g of hexamethyleneimine (284 mL, 2.496 moles, 1 eq.). The solution was then allowed to stir at 140°C, and 259 g of lactic acid in water (93 wt% content, 215.83 mL, 2.674 moles, 1.07 eq.) was progressively added into the reactor vessel over 2h00 period. Following the lactic acid addition, the mixture was allowed to stir at 170-180°C and the reaction progress was followed up thanks to1H NMR analysis. Water which was formed as a by-product distilled out from the reaction vessel during the course of the reaction and the mixture turned orange-red. After 8h00 stirring at 170-180°C, around 88 mL of distillate was recovered and1H NMR analysis showed approximately 73% conversion rate and after 12h00 stirring at 170-180°C, 96 mL of distillate was recovered with 90% conversion according to1H NMR analysis. The mixture was then distillated under vacuum and a main fraction (Teb.: 149°C, 10 mbar) was obtained as a pale yellow liquid (213.3 g) along with two intermediate fractions also collected: - Teb. = 135°C, 13 mbar, 17.6 g. - Teb. = 148°C, 10 mbar, 25.1 g.1H NMR analysis of the main fraction showed the presence of the desired product Ic along with residual amounts of hexamethyleneimine and lactic acid. Therefor an additional purification through vacuum distillation was performed in the presence of 12.6 of NaHCO3in order to salify the residual lactic acid to its non-volatile sodium salt. A main fraction was then distilled at 136°C, 5 mbar corresponding to the desired product Ic (143.4 g) with good purity. Acid value: 0.38 mg(KOH) / g Karl Fischer: 0.03 wt% (H2O). 1H NMR (CDCl3, 400 MHz) δ (ppm): 4.37 (q, J = 6.7 Hz, 1H), 3.85 (bs, 1H), 3.68 (ddd, J = 13.9 Hz, J = 6.9 Hz, J = 4.3 Hz, 1H), 3.4 (dt, J = 14.3 Hz, J = 6.0 Hz, 1H), 3.29 (ddd, J = 13.9 Hz, J = 7.8 Hz, J = 4.1 Hz, 1H), 3.26 (dt, J = 14.3 Hz, J = 6.3 Hz, 1H), 1.78-1.57 (m, 4H), 1.57-1.45 (m, 4H), 1.28 (d, J = 6.6 Hz, 3H). 13C (CDCl3, 101 MHz) δ (ppm): 174.9, 64.4, 46.9, 46.7, 29.2, 27.8, 27.3, 26.5, 21.7. Exemple 4: Synthesis of compound Id (R = -(CH2)-(CH2)-(C=O)-CH3 The reaction was conducted under an inert argon atmosphere. In a 1.5L double-jacket reactor equipped with a mechanical stirrer (4 inclined blades) and baffles, a temperature probe recording the temperature inside the reaction mass, a condenser (10°C), another temperature probe recording the temperature at the condenser bottom and a short path distillation apparatus connected to a collector were added at room temperature: - 300 g of hexamethyleneimine (340.9 mL, 3.027 moles, 1 eq.). The solution was allowed to stir (350 rpm) at 140°C and 351.5 g of levulinic acid (319.5 mL, 3.027 moles, 1eq.) was progressively added into the reaction vessel over or period of 1h30. Then the mixture was allowed to stir at 180°C and the reaction progress was followed-up by1H NMR analysis. Water that was formed during the amidification reaction was progressively distilled out in order to drive the reaction toward completion. After 2h30 stirring at 180°C, approximately 52 g of liquid has been recovered into the collector. Then the product was purified by vacuum distillation allowing to revover the main fraction (Teb. = 156°C, 5 mbar, 130.5 g). Two intermediate fractions were also collected: - Teb. = 56°C, 15 mbar (23 g). - Teb.= 163°C, 8 mbar) (59 g). The main fraction contained the desired product contaminated with traces of hexamethyleneimine (~10 mol%). Therefor it was diluted in 2-MeTHF and washed with an aqueous solution of NaOH 0.5 M. The aqueous phase was conter-extracted with 2-Me-THF after saturation with NaCl. The organic phases were then gathered, dried over MgSO4 and evaporated to afford the purified product. Over ageing a light precipitate appeared requiring to filter the product in order to obtain finally 95.5 g of the desired product. Base value: 0.088 meq. / g. Karl Fischer: 0.3 wt% (H2O). 1H NMR (CD3OD, 400 MHz) δ (ppm): 3.54 (t, J = 6.0 Hz, 2H), 3.49 (t, J = 6.0 Hz), 2.77 (t, J = 6.3 Hz, 2H), 2.62 (t, J = 6.3 Hz, 2H), 2.18 (s, 3H), 1.84- 1.74 (m, 2H), 1.73-1.54 (m, 6H).13C (CD3OD, 101 MHz) δ (ppm): 210.4, 173.8, 49.2, 47.4, 38.9, 30.0, 29.9, 28.7, 28.2, 27.9. Example 5: Active ingredient solubility tests 5 Solubility tests with different active ingredients (fungicides) were carried out in the solvents of the present invention at different concentrations and at 25°C. For this purpose, mixtures were prepared by solubilizing an active ingredient at a 10 certain percent weight / volume (%w / v) in a solvent system. The mixture was stirred at 60 rpm using a rotator drive during 24h at room temperature. The solubilizing capabilities of each system was based on visual observations at room temperature. At a given percentage, if the mixture is limpid (homogeneous transparent liquid phase), the active ingredient is considered to be 15 soluble in a solvent. If a turbid solution, crystal, suspended particles, or deposit appears, the maximal solubility of the active ingredient is reached. The maximal solubility is defined as the maximum amount of active ingredient that can be dissolved in the solvent system, equal to the amount at which the mixture remains limpid. The higher the active ingredient percentage is in a solvent, the 20 more efficient the solvent is for this active ingredient. Table 1 shows the maximum solubility (% w / v) of different active ingredients in the solvents according to Compounds Ia, Ib, Ic and Id prepared in Examples 1, 2, 3 and 4 respectively, compared to other single solvents 25 (Polarclean, NBP, acetophenone, N,N-dimethyl lactamide, cyrene and ADMA 10). It can be seen from Table 1 that Compound Ia is an efficient solvent for various fungicides, which shows an improved solubility performance compared to the other solvents tested. Where the solubility performance of the Compound 30 Ia is not improved, it is equal compared to the other solvents tested. It can furthermore be seen from Table 1 that Compound Ib is also an efficient solvent for various fungicides. While the solubility performance of Compound Ib is reduced compared to Compound Ia, it still shows an improved solubility performance with respect to selected fungicides in selected solvents especially solvents that are not water miscible such as acetophenone and ADMA- 10. 5 Table 2 shows the maximum solubility (% w / v) of different active ingredients in the solvents according to Compounds Ia and Ib prepared in Example 1 and 2, respectively, compared to solvent combinations comprising 70% w / v of ADMA10 and 30% of a different solvent (Polarclean, and NBP). Those solvent combinations are provided to improve the stability performance of 10 ADMA10 alone. It can be seen from Table 2 that Compound Ia is an efficient solvent for various fungicides, which shows improved solubility performance compared to the solvent combinations tested. It can furthermore be seen from Table 2 that also Compound Ib is an 15 efficient solvent for various fungicides, which in most cases shows improved or equal solubility performance compared to the solvent combinations tested. Table 3 shows the maximum solubility (% w / v) of different active ingredients in the solvents according to compounds Ia and Ib prepared in 20 Example 1 and 2, respectively, compared to solvent combinations comprising 70% w / v of acetophenone and 30% of a different solvent (Polarclean, and NBP). Those solvent combinations are provided to improve the stability performance of acetophenone alone. It can be seen from Table 3 that Compound Ia is an efficient solvent for 25 various fungicides, which in most cases shows an improved or equal solubility performance compared to the solvent combinations tested. It can furthermore be seen from Table 3 that also Compound Ib is an efficient solvent for some selected fungicides (Prothioconazole, Tebuconazole and Fluxapyroxad) showing improved solubility performances compared to the 30 solvents combinations tested for some active ingredients. - -yx nyx niolfiibolfroribrorTts53020203525304015203Tts5302010252-dax-d aaaxxuorxuo llr Fyp5403025203Fyp540303025354510203 5- le-ole onoz nozefanefiainDoc0553025203Doc05530404030505020404-n-nefefulflulflaiSca0451015151aiSca04510151520301015201-n-ynyxibxi ozorobzorAts02 5 2 5 5Ats02 50151510202 25102lele - oz-uouzbeanbeanToc0504520353Toc05045352030502520301-o leihotz-o leoanihoP c 5 5 2 4 5 1tzr o 550554030 5 5 5 0 0oarnPoc5505540505 / I I) ) / 0)adbe laIbI 0 0dcIddIdnoytnun nh d d7(3(7(ane0 te en n0 0na 0)neounpounpoupop le hp 1Aimide uouo1 1 10AAleA3(lcvrmmmlaP toMd-mane p pcmmMMrlaMPoS o o omooPBecD,Ntclry o oDDoPDB C C C C N A A NaC C C A A A Nyr2 ytlern0 b tnE1 2 3 4 5 6 7 8 9 1 aT E1 2 3 4 5 - yxonlfiibrorTts5302045353-daaxxuolrFyp5403510252- le onozefianDoc0553055454-nefulfl aiSca0451015102-ynxiobzorAts02 5025151le-uozbeanToc0504020203-o leihotzoarnPoc5505525304 / ) / 0)Ie70(e) 7(aIb0 edndnonun no3(noenen nouha ephp le hp)0pop tcr3(momooetcoec latoPoPecB C C A A A N3le yrbatnT E1 2 3 4 5 Example 6. Biodegradability assessment. The biodegradability of the most performing compound Ia was assessed following the guidelines OECD302B (inherent biodegradability assay). The biodegradability rate measured over time is shown in the table below (average of 2 replicas): Day # Biodegradation Rate (%) 5 < 5 6 26 7 54 14 > 90 We can clearly observe that the compound Ia displays a good biodegradability profile (considered as inherently biodegradable).

Claims

C L A I M S 1. Use of a compound of formula (I)wherein R is selected group consisting of hydrogen, –(C1- C11)alkyl and –(C3-C11)alkenyl, wherein –(C1-C11)alkyl and –(C3- C11)alkenyl are optionally substituted with a hydroxy group and / or an oxo group, with the proviso that R does not contain a C-C double bond in α,β- position relative to the amide group of the compound of formula (I) as a solvent.

2. Use according to claim 1, wherein in the compound of formula (I) R is selected from the group consisting of hydrogen, -CH3, -(OH)CH-CH3, n-C3H7, CH3-C(=O)-CH2-CH2- , n-C9H19.

3. Use according to claim 1 or 2, wherein in the compound of formula (I) R is selected from the group consisting of -CH3, -(OH)CH-CH3 and n-C3H7.

4. Use according to any one of claims 1 to 3 for the solubilization of an agricultural active compound.

5. Use according to claim 4, wherein the agricultural active compound is selected from the group consisting of pesticides, biopesticides, fertilizers, fertilizer stabilizers, nutrients, biostimulants, plant growth regulators, natural plant defense enhancers, inoculants and mixtures thereof. 5 6. Use according to claim 4 or 5, wherein the agricultural active compound is a pesticide selected from the group consisting of an herbicide, an insecticide, an acaricide, a fungicide, algicide, a molluscicide, a miticide, a nematicide, a biocide and a rodenticide and mixtures thereof. 10 7. Use according to any one of claims 4 to 6, wherein the agricultural active compound is a fungicide selected from azoles such as prothioconazole, epoxiconazole, difenoconazole, propiconazole, cyproconazole and tebuconazole; strobilurins such as azoxystrobin, trifloxystrobin, 15 picoxystrobin, fluoxastrobin, pyraclostrobin; and carboxamides such as bixafen, fluxapyroxad, benzovindiflupyr and fluopyram; and mixtures thereof.

8. Use according to claim 4 or 5, wherein the agricultural active compound is a 20 fertilizer stabilizer selected from the group of N-(n-butyl)thiophosphoric triamide (NBPT) and dicyandiamide (DCD), and mixtures thereof.

9. Use according to any one of claims 1 to 8 in an agriculture formulation. 25 10. Use according to claim 9, wherein the agriculture formulation is a pesticide containing formulation or a fertilizer formulation, preferably an enhanced efficiency fertilizer formulation.

11. Use according to claim 9 or 10, wherein the agriculture formulation is in the 30 form of 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 treatments (FS), preferably in the form of an emulsifiable concentrate (EC), concentrated emulsion in water (EW), microemulsion (ME), suspoemulsion (SE), oil dispersion (OD), dispersible concentrate (DC), capsule suspension (CS), soluble liquid (SL), 5 more preferably in the form of an emulsifiable concentrate (EC), an emulsion in water concentrate, a microemulsion concentrate, a suspoemulsion concentrate, an oil dispersion concentrate or a dispersible concentrate, and particularly preferably in the form of an emulsifiable concentrate. 10 12. An agriculture formulation comprising a) an agricultural active compound as defined in any one of claims 5 to 8, and b) a compound as defined in any one of claims 1 to 3; d) optionally at least one co-solvent, 15 c) optionally at least one emulsifier and / or one surfactant, and d) optionally water.

13. Agricultural formulation according to claim 12, which is in a form as defined in claim 11. 20 14. Agriculture formulation according to claim 12 comprising a) from 0.01 to 90% by weight, preferably from 5 to 60% by weight, of at least one agricultural active compound as defined in any one of claims 5 to 25 7, preferably at least one pesticide as define in claim 6, relative to the total weight of the agriculture formulation; b) from 5 to 90% by weight, preferably from 10 to 90% by weight, in particular from 30 to 90% by weight, for instance from 30 to 80% by weight, of a compound as defined in any one of claims 1 to 3, relative to 30 the total weight of the agriculture formulation; c) from 0.1 to 40% by weight, preferably from 1 to 30% by weight, of at least one co-solvent, relative to the total weight of the agriculture formulation,d) from 0.05 to 40% by weight, preferably from 0.1 to 35% by weight, more preferentially from 0.5 to 30% by weight, in particular from 1 to 25% by weight, for instance from 1 to 5% by weight, of at least one surfactant, relative to the total weight of the agriculture formulation, and 5 e) from 5 to 90% by weight, preferably from 10 to 80% by weight, in particular from 25 to 70% by weight, of water, relative to the total weight of the agriculture formulation.

15. Use according to any one of claims 1 to 14, wherein the use of the 10 compound of formula (I) as a solvent includes the use as a co-solvent and / or as a crystallization inhibitor, preferably in an agricultural formulation as defined in claims 12 to 14. 15 20

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