Solvent compositions for agrochemical formulations

Abstract

The invention relates to a solvent composition comprising at least one specific levulinic acid ester as a first solvent and at least one specific dioxolane-based solvent as a second solvent. The invention also relates to the use of the solvent composition for producing agrochemical formulations and to the agrochemical formulations themselves.

Description

[0001] The present invention relates to a solvent composition comprising at least one specific levulinic acid ester as a first solvent and at least one specific dioxolane-based solvent as a second solvent.

[0002] The invention also relates to the use of the solvent composition for preparing agrochemical formulations and to the agrochemical formulations themselves.

[0003] Agriculture uses many agricultural materials, such as fertilizers or pesticides, for example insecticides, herbicides or fungicides. They are also called active plant protection products or active materials or active substances. Agricultural materials are usually products in pure or highly concentrated form.

[0004] Usually, agricultural materials are not used as pure substances, but they are usually formulated with other ingredients depending on the field of application and the desired physical composition of the form of use.

[0005] Regardless of the type of formulation and whether it contains one or more agricultural materials, in particular in the agricultural sector, efforts are made to achieve the highest possible concentration of the agricultural material in the respective formulation, since a high concentration of the agricultural material allows a reduction in the volume to be applied and thus results in savings in terms of the auxiliary 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.

[0006] Typically, such formulations comprise combinations of different agricultural materials rather than individual agricultural materials in order to exploit together the properties of the individual agricultural materials when applied, or because the individual agricultural materials act synergistically in combination, ie, produce a superadditive increase in activity.

[0007] In the application of products for agricultural use, it is well known to combine two or more agricultural materials with different mechanisms of action and / or different biological targets in order to broaden the spectrum of action of the mixture relative to those of the agricultural materials used individually and, for example, to prevent the development of resistance phenomena from harmful organisms or species, which tend over time to reduce the effectiveness of the pesticide products used.

[0008] Depending on the respective physicochemical characteristics of various agricultural materials and their loading in the target formulation, identification of suitable co-formulations to obtain chemically and physically stable formulations can be very challenging.

[0009] For agricultural materials with low or relatively low water solubility, the use of appropriate solvents to prepare 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) is of particular interest. More details on the definition of the above formulations can be found in the "Guidance document for the generation of data on the physical, chemical and technical properties of plant protection products in accordance with Regulation (EC) No 1107 / 2009 of the European Parliament and of the Council on the placing of plant protection products on the market".

[0010] Such concentrated formulations of agricultural materials are usually diluted prior to agricultural use. Dilution by farmers is usually carried out by mixing the agrochemical formulation with water.

[0011] Depending on the characteristics of the concentrated formulation, the diluted formulation may be in the form of a solution, emulsion, suspension, or suspoemulsion.

[0012] In addition, agrochemical formulations often contain compounds that can obtain these physical forms. These can be, for example, surfactants, polymers, solvents, mineral carriers and / or dispersants. Quite often, these compounds do not have any active properties, but rather have intermediate properties that assist in formulation. Therefore, it is often desirable to limit their amount in order to limit cost and / or any damage to the environment.

[0013] In addition, some solid agricultural materials are often difficult to prepare.For some agricultural materials, it is difficult to produce the concentrated formulation that is easy to dilute, stable and does not have substantial disadvantages (actual or perceived shortcomings) for farmers about safety, toxicity and / or ecotoxicity.For some agricultural materials, it is difficult to prepare with relatively high concentration under enough stability.Especially, it is necessary to avoid the appearance of crystal, particularly at low temperatures and / or during the dilution period and / or during the storage of the diluted composition, particularly at low temperatures during storage.Crystal may have a harmful effect, especially obstructs the filter for spreading the device of the diluted composition, obstructs the spraying device, reduces the overall activity of the formulation, produces the unnecessary problem of the waste management program for removing crystal and / or causes the poor distribution of one or more agricultural materials on farmland.

[0014] It is known to use solvent systems based on a single solvent such as N-methylpyrrolidone (NMP). This solvent is able to dissolve large amounts of agricultural materials and avoid the formation of crystals, but it also presents risks, especially for operators and users who handle it.

[0015] The agrochemical industry is looking for new solvent compositions that have desirable properties for agricultural applications, such as, for example, good solubility efficiency for agricultural materials and low miscibility with water. Furthermore, the cost of the solvent compositions should generally be moderate, and preferably they should have a favorable toxicological and / or ecotoxicological profile, in particular low toxicity and / or low hazard potential, and / or low volatility (low VOC—volatile organic compounds) and / or advantageously high biodegradability and / or renewability.

[0016] Therefore, there is a continuing need to provide solvent systems for agricultural use that:

[0017] - possesses great modularity, i.e. the ability to be used in a large number of agricultural materials,

[0018] - has the potential to dissolve significant amounts of agricultural materials,

[0019] - have a high compatibility with several agricultural materials combined together, for example in order to be able to achieve an enhanced biological efficacy,

[0020] - avoid the appearance of crystals, even under harsh conditions, and / or

[0021] - presents a good safety and sustainability profile, with no hazard classification and / or ecotoxicology or with a low hazard classification and / or ecotoxicology,

[0022] Even for complex associations of agricultural materials (e.g. at high loadings) or for hydrophobic materials.

[0023] Preferably, the solvent system should also have good inherent or ready biodegradability and a high renewable carbon index (recyclability).

[0024] These objects are achieved by the present invention, the subject of which is a composition comprising:

[0025] (i) 35% to 95% by weight, relative to the total weight of the composition, of at least one first solvent of general formula (A):

[0026]

[0027] wherein R represents a linear or branched (C3-C6) alkyl group; and

[0028] (ii) at least one second solvent having the general formula (C):

[0029]

[0030] in,

[0031] - R1 and R2 are independently linear or branched C1-C 12 Alkyl, C4-C 12 Cycloalkyl or aryl,

[0032] -R3 is H, linear or branched (C1-C6) alkyl, (C3-C8) cycloalkyl, or

[0033] -C(O)R4 group, wherein R4 is a linear or branched C1-C4 alkyl group or a C5-C6 cycloalkyl group.

[0034] The solvent compositions according to the present invention have a high dissolution efficiency. In particular, the compositions according to the present invention preferably exhibit good modularity, good potential for dissolving significant amounts of agricultural materials, and high compatibility with several agricultural materials combined, for example, to achieve enhanced biological efficacy. It should be noted that the dissolution potential of the solvent compositions according to the present invention is even better for agricultural materials other than N-(n-butyl)-thiophosphoric acid triamide (NBPT).

[0035] The term solvent may especially indicate a product that is liquid at the temperature of use, which may help to make a solid substance liquid, or prevent / delay the solidification or crystallization of a material in liquid form. It may generally have a melting point of less than or equal to 20°C, in particular 5°C, for example 0°C.

[0036] Furthermore, it has been noted that the compositions according to the invention can preferably guarantee good performance upon dilution, even for highly loaded formulations, and avoid / delay the appearance of crystals, even under harsh conditions.

[0037] Furthermore, the composition according to the invention presents a good safety and sustainability profile, advantageously with no or low hazard classification and ecotoxicology.

[0038] In particular, the solvent composition according to the present invention preferably has good (intrinsic or ready) biodegradability, or high ultimate aerobic biodegradability in soil, and may generally exhibit a high Renewable Carbon Index.

[0039] The Renewable Carbon Index (RCI) is a way to quantify the "eco-friendly" characteristics of ingredients and products. The higher the RCI, the better the renewable characteristics of the ingredient or product.

[0040] The present invention also provides the use of the compositions according to the invention for preparing agrochemical formulations.

[0041] The present invention also provides for the use of the compositions according to the invention as solvents, in particular in agrochemical formulations.

[0042] The present invention also provides an agrochemical formulation comprising at least one agricultural material and the solvent composition according to the invention.

[0043] According to a preferred embodiment of the invention, the agrochemical formulation is an agrochemical formulation having a high concentration of one or more agrochemical materials. For economic reasons (in fact, such compositions make it possible to reduce the total weight of the formulation and therefore reduce its transportation costs), it is particularly advantageous to use concentrated formulations, which are then generally diluted to the desired concentration by the end user.

[0044] Other characteristics, aspects and advantages of the invention will appear more clearly on reading the following description and examples.

[0045] In this manual, and unless otherwise stated:

[0046] - the expression "at least one" is equivalent to and can be replaced by the expression "one or more";

[0047] - the expression "between" is equivalent to and can be replaced by the expression "ranging from", and is intended to include the limit values;

[0048] - for the purposes of the present invention, the expression "greater than" and, respectively, the expression "less than" are intended to mean an open range that is strictly greater than, respectively strictly less than, and therefore does not include the limit values;

[0049] - The expression "alkyl" refers to a group having the general formula C n H 2n+1 acyclic, straight-chain or branched alkyl groups.

[0050] The composition according to the invention is a composition which can preferably be used as a solvent and which comprises a mixture of at least one first solvent and at least one second solvent, and preferably at least one third solvent.

[0051] First solvent

[0052] The composition according to the invention comprises at least one first solvent having the general formula (A):

[0053]

[0054] wherein R represents a linear or branched (C3-C6) alkyl group.

[0055] The first solvent having the general formula (A) is an ester of levulinic acid.

[0056] The group R in formula (A) represents a straight-chain or branched alkyl group containing at least 3 carbon atoms.

[0057] More preferably, the group R in formula (A) represents a linear (C3-C6)alkyl group.

[0058] And even more preferably, the group R in formula (A) represents a linear or branched alkyl group containing at least 4 carbon atoms, in particular a linear or branched (C4-C6)alkyl group, and more particularly a linear (C4-C6)alkyl group.

[0059] Advantageously, the first solvent is butyl levulinate (i.e. R is a linear or branched C4-alkyl group), and more particularly n-butyl levulinate (i.e. R is n-butyl); in addition to being of biological origin, butyl levulinate is advantageously completely immiscible in water (which is preferred, for example, to formulate agrochemical formulations in the form of emulsifiable concentrates).

[0060] Among examples of solvents of formula (A) that can be used according to the invention, mention may be made of W448001 or W220701 sold by Sigma-Aldrich, and preferably of GFbio ReSolv 200 (butyl levulinate) sold by GF Biochemicals (formerly named NXT SOLV 200).

[0061] Preferably, the total amount of one or more first solvents of general formula (A) ranges from 35% to 90% by weight, even more preferably from 35% to 85% by weight, better from 35% to 80% by weight, even better from 50% to 80% by weight, and for example from 55% to 70% by weight relative to the total weight of the composition.

[0062] Preferably, the total amount of butyl levulinate ranges from 35% to 90% by weight, even more preferably from 35% to 85% by weight, better still from 35% to 80% by weight, even better still from 50% to 80% by weight and for example from 55% to 70% by weight relative to the total weight of the composition.

[0063] Renewable carbon generally requires avoiding or replacing all carbon sources that use any additional fossil carbon from the geosphere. Renewable carbon can come from the biosphere, atmosphere, or technosphere, but not from the geosphere.

[0064] Renewable carbon is defined herein 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.

[0065] The Renewable Carbon Index (RCI) is defined herein as a 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 in the first solvent is renewable carbon, the RCI is 0.8.

[0066] For a first solvent blend, the RCI of the first solvent is the weighted average of each first solvent of the blend.

[0067] Preferably, the one or more first solvents used in the composition according to the invention have a Renewable Carbon Index (RCI) of at least 0.25, more preferably at least 0.3, even more preferably at least 0.4, in particular at least 0.5 and for example at least 0.55.

[0068] Preferably, the butyl levulinate used in the advantageous compositions according to the invention has an RCI of at least 0.4, preferably at least 0.5 and more preferably at least 0.55.

[0069] Second solvent

[0070] The composition according to the invention comprises at least one second solvent having the general formula (C):

[0071]

[0072] in,

[0073] - R1 and R2 are independently linear or branched C1-C 12 Alkyl, C4-C 12 Cycloalkyl or aryl,

[0074] -R3 is H, linear or branched (C1-C6) alkyl, (C3-C8) cycloalkyl, or a -C(O)R4 group, wherein R4 is linear or branched C1-C4 alkyl or C5-C6 cycloalkyl;

[0075] In a preferred embodiment:

[0076] - R1 and R2 are independently linear or branched (C1-C 12 )alkyl, and / or

[0077] - R3 is H or a linear or branched (C1-C6) alkyl group.

[0078] More preferably, according to this embodiment, R1 and R2 are independently of each other linear or branched (C1-C4)alkyl, and R3 is H.

[0079] In another preferred embodiment, R1 and R2 are independently selected from the group consisting of methyl, ethyl, isopropyl, n-propyl, isobutyl, n-butyl, tert-butyl, n-pentyl, cyclopentyl, cyclohexyl or phenyl, and more preferably methyl.

[0080] Advantageously, in formula (C) above, R3 is H or a -C(O)R4 group, wherein R4 is methyl, ethyl, isopropyl, n-propyl, isobutyl, n-butyl or tert-butyl. More preferably, R3 is H.

[0081] A very preferred embodiment is when R1 and R2 are methyl groups and R3 represents a hydrogen atom. The corresponding commercial compounds are, for example Li-Tec 2V( SL191) or Solketal. This compound can be synthesized under well-known classical conditions by the reaction between glycerol and acetone. Glycerol can be obtained as a by-product of biodiesel production in the transesterification process of triglycerides, for example.

[0082] An example is where R1 and R2 are methyl and R3 is a -C(O)R4 group, wherein R4 is methyl. The corresponding commercial compounds can be synthesized by transesterification of Solketal with alkyl acetates under well-known classical conditions.

[0083] In another embodiment, R1 is methyl, R2 is isobutyl and R3 is H. The corresponding commercial compounds can be synthesized by reaction between glycerol and methyl isobutyl ketone under well-known classical conditions.

[0084] In another specific embodiment, R1 is methyl, R2 is phenyl and R3 is H. The corresponding compounds can be synthesized by reaction between glycerol and acetophenone under well-known classical conditions.

[0085] According to certain embodiments, the compound having formula (C) may be a bio-based compound.

[0086] According to another particular embodiment, the at least one second solvent comprises a compound of formula (C) and a compound of formula (C′), wherein R1, R2 and R3 have the same meanings as for formula (C).

[0087]

[0088] More preferably, the second solvent having formula (C) is 2,2-dimethyl-4-hydroxymethyl-1,3-dioxolane.

[0089] Preferably, the total amount of the one or more second solvents of general formula (C) ranges from 1% to 50% by weight, more preferably from 1% to 45% by weight, even more preferably from 2% to 40% by weight, in particular from 5% to 35% by weight, and for example from 5% to 30% by weight relative to the total weight of the composition.

[0090] Preferably, the total amount of 2,2-dimethyl-4-hydroxymethyl-1,3-dioxolane ranges from 1% to 50% by weight, more preferably from 1% to 45% by weight, even more preferably from 2% to 40% by weight, in particular from 5% to 35% by weight and for example from 5% to 30% by weight relative to the total weight of the composition.

[0091] Preferably, the weight ratio of the total content of one or more first solvents having general formula (A) to the total content of one or more second solvents having general formula (C) ranges from 0.1 to 20; more preferably from 0.5 to 15; even more preferably from 1 to 15; better still from 1 to 10; in particular from 1 to 8; and for example from 1.5 to 7.5.

[0092] Preferably, the weight ratio of the total content of one or more first solvents having general formula (A) to the total content of one or more second solvents having general formula (C') ranges from 0.1 to 20; more preferably from 0.5 to 15; even more preferably from 1 to 15; better still from 1 to 10; in particular from 1 to 8; and for example from 1.5 to 7.5.

[0093] When the composition according to the invention contains butyl levulinate and 2,2-dimethyl-4-hydroxymethyl-1,3-dioxolane, the weight ratio of the total content of butyl levulinate to the total content of 2,2-dimethyl-4-hydroxymethyl-1,3-dioxolane may preferably range from 0.1 to 20; more preferably from 0.5 to 15; even more preferably from 1 to 15; better still from 1 to 10; in particular from 1 to 8; and for example from 1.5 to 7.5.

[0094] Typically, the composition according to the invention exhibits a Renewable Carbon Index (RCI) of at least 0.25, more preferably at least 0.3, even more preferably at least 0.4, in particular at least 0.5 and for example at least 0.55.

[0095] Additional solvents

[0096] Preferably, the composition according to the invention further comprises one or more additional solvents.

[0097] According to this preference, the composition comprises at least one first solvent of formula (A), at least one second solvent of formula (C) and one or more further solvents different from the solvent of formula (A) or (C).

[0098] More preferably, the additional solvents that may be used in the composition according to the invention are chosen from:

[0099] -amide ester solvent,

[0100] - amide solvent,

[0101] - a solvent selected from levoglucosone, dihydrolevoglucosone or a derivative thereof,

[0102] - an aromatic solvent other than the solvent of formula (A) or (C),

[0103] - an ester or diester solvent other than the solvent of formula (A),

[0104] - an alkyl acetate solvent other than the solvent of formula (A),

[0105] - sulfoxide solvent, and

[0106] - mixtures thereof.

[0107] Even more preferably, the additional solvent that may be used in the composition according to the invention is chosen from amide ester solvents, amide solvents and mixtures thereof.

[0108] The amide ester solvents that can be used in the composition according to the present invention are preferably selected from amide ester solvents having formula (B):

[0109] R 1 CONR 2 R 3 (B)

[0110] in:

[0111] -R 1 is a linear or branched saturated aliphatic group having 1 to 6 carbon atoms, which is substituted by one or more functional groups chosen from -OH groups and / or -COOR' groups, wherein R' is (C1-C6)alkyl, in particular (C1-C4)alkyl, and more in particular (C1-C2)alkyl,

[0112] -R 2 and R 3 are identical or different and are (C1-C6)alkyl, in particular (C1-C4)alkyl, and more in particular (C1-C2)alkyl,

[0113] -R 1 and R 2or R 3 The rings may together form a ring containing 4 to 6 carbon atoms and may be optionally substituted by one or more (C1-C4)alkyl groups and / or one or more groups selected from -OH groups, -OR' groups, -COOR' groups and -CONR 4 R 5 The functional group of the group wherein R' is (C1-C6) alkyl, particularly (C1-C4) alkyl, and more particularly (C1-C2) alkyl, and R 4 and R 5 are the same or different, indicating (C1-C6)alkyl, particularly (C1-C4)alkyl, and more particularly (C1-C2)alkyl.

[0114] Preferably, the group R in formula (B) 1 represents a group of formula -Z-COOR', wherein R' is a methyl group and Z is a linear or branched divalent alkylene group containing 1 to 6 carbon atoms, in particular 2 to 4 carbon atoms.

[0115] More preferably, Z is a linear or branched divalent alkylene group containing 4 carbon atoms, and even more preferably, Z is a branched divalent alkylene group containing 4 carbon atoms.

[0116] According to a preferred embodiment, the amide ester solvent having formula (B) is selected from those having the following formula (B'):

[0117] R'OOC-Z-CONR2R3(B')

[0118] in,

[0119] - Z is a divalent (C1-C6)alkylene group, preferably a (C2-C5)alkylene group, more preferably a (C4)alkylene group, and

[0120] - R', R2 and R3 are identical or different, indicating (C1-C6)alkyl, preferably (C1-C4)alkyl, more preferably (C1-C2)alkyl, and even better methyl.

[0121] Preferably, according to this embodiment, Z in formula (B') is a divalent (C4)alkylene group, more preferably a divalent alkylene group having the formula -CH(CH3)-CH2-CH2-.

[0122] Preferably, according to this embodiment, R', R2 and R3 are (C1-C4)alkyl, in particular methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, tert-butyl. And more preferably, R', R2 and R3 are identical and in particular (C1-C2)alkyl. More advantageously, R', R2 and R3 are identical and represent methyl.

[0123] Preferably, the one or more esteramide solvents are selected from compounds of formula (B'), wherein Z is a (C4)alkylene group, and R', R2 and R3 are methyl groups. Very preferably, the ester-amide solvent comprises at least one compound of formula (B'), wherein Z is an alkylene group of formula -CH(CH3)-CH2-CH2, and R', R2 and R3 are methyl groups.

[0124] According to a particularly preferred embodiment, the composition according to the present invention further comprises at least one third solvent selected from amide ester solvents having formula (B) above; preferably selected from amide ester solvents having formula (B') above. More preferably, according to this embodiment, the composition according to the present invention comprises methyl-5-(dimethylamino)-2-methyl-5-oxopentanoate as the third solvent.

[0125] Sold by Solvay Polarclean is an example of a very suitable commercial solvent that can be used as an additional solvent according to the present invention.

[0126] Preferably, the total amount of the one or more amide ester solvents of general formula (B) ranges from 1% to 60% by weight, more preferably from 5% to 50% by weight, even more preferably from 10% to 45% by weight, in particular from 10% to 40% by weight, for example from 20% to 40% by weight, relative to the total weight of the composition.

[0127] Preferably, the total amount of one or more amide ester solvents of general formula (B') ranges from 1% to 60% by weight, more preferably from 5% to 50% by weight, even more preferably from 10% to 45% by weight, in particular from 10% to 40% by weight, for example from 20% to 40% by weight, relative to the total weight of the composition.

[0128] Preferably, the total amount of methyl 5-(dimethylamino)-2-methyl-5-oxopentanoate ranges from 1% to 60% by weight, more preferably from 5% to 50% by weight, even more preferably from 10% to 45% by weight, even better from 10% to 40% by weight, for example from 20% to 40% by weight relative to the total weight of the composition.

[0129] The amide solvents that can be used in the composition according to the invention are different from the solvents of general formula (B) as defined above and are preferably chosen from amide solvents of formula (D):

[0130] R”-CONR2R3(D)

[0131] Wherein R" is a straight chain or branched chain (C3-C 19 ) alkyl, preferably linear or branched (C7-C 19)alkyl, more preferably a straight-chain alkyl containing 7, 8 or 9 carbon atoms, and even more preferably a straight-chain (C9)alkyl, and R2 and R3 may be identical or different, indicating a hydrogen atom or a (C1-C6)alkyl, preferably a (C1-C4)alkyl, more preferably a (C1-C2)alkyl, and in particular a methyl group, with the proviso that if R2 is a hydrogen atom, R3 is a (C1-C6)alkyl.

[0132] According to a preferred embodiment, R2 and R3 are identical.

[0133] According to another preferred embodiment, R″ is a linear alkyl group containing 7, 8 or 9 carbon atoms, and R2 and R3 are identical and indicate a (C1-C2)alkyl group.

[0134] More preferably, the amide solvent is N,N-dimethyldecylamide, i.e. wherein R" is a linear (C9) alkyl group and R2 and R3 are methyl groups (such as for example the amide sold by Solvay). ADMA 10).

[0135] According to a particularly preferred embodiment, the composition according to the present invention further comprises at least one third solvent selected from amide solvents having the above formula (D). More preferably, according to this embodiment, the composition according to the present invention comprises N,N-dimethyldecylamide as the third solvent.

[0136] Preferably, the total amount of amide solvents of formula (D) ranges from 1% to 70% by weight, more preferably from 5% to 50% by weight, even more preferably from 10% to 45% by weight, in particular from 20% to 40% by weight, and for example from 30% to 40% by weight relative to the total weight of the composition.

[0137] Preferably, the total amount of N,N-dimethyldecylamide ranges from 1% to 70% by weight, more preferably from 5% to 50% by weight, even more preferably from 10% to 45% by weight, in particular from 20% to 40% by weight and for example from 30% to 40% by weight relative to the total weight of the composition.

[0138] Additional solvents that may be used in the composition according to the invention may be selected from levoglucosone, dihydrolevoglucosone or derivatives thereof.

[0139] Levoglucosone is a bicyclic α,β-unsaturated ketone containing a protected aldehyde. Highly dehydrated sugars are derived from cellulose and thus provide a bio-based solvent that is attractive as a "green" solvent.

[0140] Levoglucosone having the molecular formula C6H6O3 is ((1S,5R)-6,8-dioxabicyclo[3.2.1]oct-2-en-4-one) of the following formula (I):

[0141]

[0142] According to the present invention, the derivative means a derivative of levoglucosone or a derivative of dihydrolevoglucosone.

[0143] Generally, a derivative of levoglucosone is a compound that can be synthesized directly and / or indirectly from levoglucosone. In other words, levoglucosone can be a starting material and / or an intermediate material for synthesizing a levoglucosone derivative.

[0144] Dihydrolevulinone is derived from levulinone by hydrogenation of levulinone (e.g. over a supported palladium catalyst). Commercially, dihydrolevulinone is available from Circa Group Pty Ltd. as (RTM) available.

[0145] Dihydro-levulinic acid ketone is a chiral dipolar aprotic solvent. Dihydro-levulinic acid ketone having the molecular formula C6H8O3 is ((1S,5R)-6,8-dioxabicyclo[3.2.1]octan-4-one) having the following formula (II):

[0146]

[0147] As derivatives of dihydrolevoglucosenone, ketal derivatives of dihydrolevoglucosenone may be mentioned, in particular cygnet 0.0 (spiro[6,8-dioxabicyclo[3.2.1]octane-4,2′-[1,3]dioxolane]), cygnet 1.0, cygnet 1.1, cygnet 2.0, cygnet 4.0 (as described in “Intelligent approach to solvent substitution: the identification of a new class of levoglucosenone derivatives” - Ana Alves Costa Pacheco et al. - ChemSusChem, 2016, 9, 3503-3512).

[0148] According to a specific embodiment, the composition according to the present invention further comprises an additional solvent selected from levoglucosone, dihydrolevoglucosone, derivatives thereof, and mixtures thereof; preferably selected from levoglucosone, dihydrolevoglucosone, and mixtures thereof.

[0149] According to a particularly preferred embodiment, the composition according to the present invention further comprises dihydrolevulinone.

[0150] Preferably, when present in the composition, the total amount of levoglucosone, dihydrolevoglucosone and derivatives thereof ranges from 1% to 60% by weight, more preferably from 5% to 50% by weight, even more preferably from 5% to 40% by weight, in particular from 8% to 30% by weight relative to the total weight of the composition.

[0151] Preferably, the total amount of dihydrolevulinone ranges from 1% to 60% by weight, more preferably from 5% to 50% by weight, even more preferably from 5% to 40% by weight, in particular from 8% to 30% by weight, relative to the total weight of the composition.

[0152] The aromatic solvents that may be used in the composition according to the invention are different from the solvents of formula (A) or (B) as defined above.

[0153] Among the aromatic solvents, toluene, xylene and C8-C 12 Mixtures of di- and tri-alkylbenzenes like

[0154] Among the aromatic hydrocarbons, mention may be made of alkylbenzenes such as toluene, dialkylbenzenes such as xylene, polynuclear aromatic hydrocarbons such as naphthalene, alkylnaphthalenes (for example dimethylnaphthalene), dialkylnaphthalenes, trialkylnaphthalenes such as dimethylmonoisopropylnaphthalene and phenylxylylethane, and mixtures thereof.

[0155] Most of these hydrocarbons are obtained by fractional distillation of crude oil and generally have a distillation range comprising about 135°C to about 305°C, with those having a distillation temperature of about 183°C to about 290°C being preferred.

[0156] Among the aromatic hydrocarbons, mention may also be made of the following commercial products: Nisseki Hisol SAS-296 (a mixture of 1-phenyl-1-xylylethane and 1-phenyl-1-ethylphenylethane, Nippon Oil Corporation), Cactus Solvent HP-MN (80% methylnaphthalene, Japan Energy Corporation), Cactus Solvent HP-DMN (80% dimethylnaphthalene, Japan Energy Corporation), Cactus Solvent P-100 (alkylbenzenes having 9 to 10 carbon atoms, Japan Energy Corporation), Cactus Solvent P-150 (alkylbenzenes, Japan Energy Corporation), Cactus Solvent P-180 (a mixture of methylnaphthalene and dimethylnaphthalene, Japan Energy Corporation), Cactus Solvent P-200 (a mixture of methylnaphthalene and dimethylnaphthalene, Japan Energy Corporation), Cactus Solvent P-220 (a mixture of methylnaphthalene and dimethylnaphthalene, Japan Energy Co., Ltd.), CactusSolvent PAD-1 (dimethyl monoisopropylnaphthalene, Japan Energy Co., Ltd.), 100 (aromatic hydrocarbons, Exxon Mobil Corporation), 150 (aromatic hydrocarbons, ExxonMobil), 200 (aromatic hydrocarbons, ExxonMobil Corporation), Ultra-Low Naphtalene Aromatic 150 (ExxonMobil Chemical Company), Ultra Low Naphtalene Aromatic 200 (ExxonMobil Chemical Company), 150ND (aromatic hydrocarbons, ExxonMobil), 200ND (aromatic hydrocarbons, ExxonMobil Corporation), Swasol 100 (toluene, Maruzen Petrochemical Co Ltd) and Swasol 200 (xylene, Maruzen Petrochemical Co Ltd).

[0157] Particular mention may be made of C8-C 12 A mixture of di- and tri-alkylbenzenes.

[0158] Such mixtures are commercially available, in particular from ExxonMobil Corporation under the name 150 and 200 is commercially available.

[0159] According to a preferred embodiment, the aromatic solvent is acetophenone.

[0160] Preferably, the total amount of aromatic solvents other than the solvent of general formula (A) or (B) ranges from 1% to 60% by weight, more preferably from 2% to 50% by weight, even more preferably from 5% to 40% by weight, in particular from 10% to 30% by weight relative to the total weight of the composition.

[0161] Preferably, C8-C 12 The total amount of di- and tri-alkylbenzenes ranges from 1% to 60% by weight, more preferably from 2% to 50% by weight, even more preferably from 5% to 40% by weight and in particular from 10% to 30% by weight relative to the total weight of the composition.

[0162] Preferably, the total amount of acetophenone ranges from 1% to 60% by weight, more preferably from 2% to 50% by weight, even more preferably from 5% to 40% by weight, in particular from 10% to 30% by weight relative to the total weight of the composition.

[0163] The ester or diester solvents that may be used as additional solvent in the composition according to the invention are different from the solvents of general formula (A) or (C) as defined above.

[0164] Among the ester or diester solvents, mention may be made of 2-ethylhexyl lactate, alkyl acetates, esters of fatty acids, fatty esters of carboxylic acids, mixtures of the methyl diesters of 2-ethylsuccinic acid, methylglutaric acid and possibly adipic acid, such as IRIS (a mixture comprising 70% to 95% by weight of dimethyl 2-methylglutarate, 5% to 30% by weight of dimethyl ethylsuccinate and 0% to 10% by weight of dimethyl adipate) and a mixture of dimethyl glutarate (e.g., 60% to 70% by weight), dimethyl succinate (e.g., 20% to 30% by weight) and dimethyl adipate (e.g., 10% to 15% by weight), such as RPDE.

[0165] According to one embodiment, the composition according to the invention comprises fatty acid esters, such as rapeseed oil esters, and in particular rapeseed oil methyl ester.

[0166] According to one embodiment, the ester or diester solvent of the composition according to the invention is a carboxylic acid ester, preferably a mixture of several carboxylic acid esters.

[0167] Preferably, the ester or diester solvent of the composition according to the invention corresponds to the formula R α OOC-A-COOR α , where Rα represents a linear or branched alkyl group containing 1 to 6 carbon atoms, and preferably represents a methyl group, and A represents a linear or branched alkylene group containing 2 to 4 carbon atoms.

[0168] According to one embodiment, the ester or diester solvent is a compound IRIS.

[0169] Preferably, the total amount of ester or diester solvents other than solvents of general formula (A) or (C) ranges from 1% to 50% by weight, more preferably from 2% to 40% by weight, even more preferably from 5% to 35% by weight, in particular from 10% to 30% by weight relative to the total weight of the composition.

[0170] The alkyl acetate solvent that may be used as additional solvent in the composition according to the invention is different from the first solvent of formula (A) as defined above.

[0171] Preferably, the alkyl group of the alkyl acetate solvent contains at least 3 carbon atoms.

[0172] More preferably, the alkyl group of the alkyl acetate solvent is a linear or branched C6-C 15 Alkyl; even more preferably C6-C 13 Alkyl; and preferably C6-C 12 alkyl.

[0173] Mention may be made especially of cyclohexyl or hexyl (n-hexyl), ethylhexyl, especially 2-ethylhexyl, octyl (n-octyl), isooctyl, decyl (n-decyl), isodecyl, tridecyl, dodecyl and 18-undecyl.

[0174] Preferably, the total amount of alkyl acetate solvents other than the solvent of general formula (A) ranges from 1% to 50% by weight, more preferably from 2% to 40% by weight, even more preferably from 5% to 35% by weight, in particular from 10% to 30% by weight relative to the total weight of the composition.

[0175] The sulfoxide solvent that can be used in the composition according to the present invention is preferably dimethyl sulfoxide (DMSO).

[0176] Preferably, the total amount of sulfoxide solvent ranges from 1% to 50% by weight, more preferably from 2% to 40% by weight, even more preferably from 5% to 35% by weight, in particular from 10% to 30% by weight, relative to the total weight of the composition.

[0177] Preferably, the total amount of dimethyl sulfoxide ranges from 1% to 50% by weight, more preferably from 2% to 40% by weight, even more preferably from 5% to 35% by weight, in particular from 10% to 30% by weight, relative to the total weight of the composition.

[0178] According to a preferred embodiment of the present invention, the composition comprises:

[0179] (i) at least one first solvent having the general formula (A) as described above, preferably butyl levulinate,

[0180] (ii) at least one second solvent having the general formula (C) as described above, preferably 2,2-dimethyl-4-hydroxymethyl-1,3-dioxolane,

[0181] (iii) at least one amide ester solvent having formula (B) as described above, preferably methyl 5-(dimethylamino)-2-methyl-5-oxopentanoate, and

[0182] (iv) optionally at least one additional solvent selected from levoglucosone, dihydrolevoglucosone, derivatives thereof, and mixtures thereof, preferably dihydrolevoglucosone.

[0183] According to another preferred embodiment of the present invention, the composition comprises:

[0184] (i) at least one first solvent having the general formula (A) as described above, preferably butyl levulinate,

[0185] (ii) at least one second solvent having the general formula (C) as described above, preferably 2,2-dimethyl-4-hydroxymethyl-1,3-dioxolane,

[0186] (iii) at least one amide solvent having formula (D) as described above, preferably N,N-dimethyldecylamide, and

[0187] (iv) optionally at least one additional solvent selected from levoglucosone, dihydrolevoglucosone, derivatives thereof, and mixtures thereof, preferably dihydrolevoglucosone.

[0188] According to another preferred embodiment of the present invention, the composition comprises:

[0189] (i) at least one first solvent having the general formula (A) as described above, preferably butyl levulinate,

[0190] (ii) at least one second solvent having the general formula (C) as described above, preferably 2,2-dimethyl-4-hydroxymethyl-1,3-dioxolane,

[0191] (iii) at least one amide ester solvent having the general formula (B) as described above, preferably methyl 5-(dimethylamino)-2-methyl-5-oxopentanoate,

[0192] (iv) at least one amide solvent having formula (D) as described above, preferably N,N-dimethyldecylamide, and

[0193] (v) optionally at least one additional solvent selected from levoglucosone, dihydrolevoglucosone, derivatives thereof, and mixtures thereof, preferably dihydrolevoglucosone.

[0194] According to another preferred embodiment of the present invention, the composition comprises:

[0195] - 20% to 90% by weight, in particular 25% to 85% by weight, of butyl levulinate as a first solvent relative to the total weight of the composition,

[0196] - 1% to 50% by weight, in particular 2% to 40% by weight, of 2,2-dimethyl-4-hydroxymethyl-1,3-dioxolane as a second solvent relative to the total weight of the composition,

[0197] - optionally one or more additional solvents selected from methyl 5-(dimethylamino)-2-methyl-5-oxopentanoate, N,N-dimethyldecylamide and mixtures thereof, and

[0198] -optionally dihydrolevulinone.

[0199] According to a particular embodiment, the composition according to the invention consists of at least one first solvent of general formula (A) and at least one second solvent of general formula (C) and optionally at least one further solvent, as previously described.

[0200] The present invention also relates to the use of a composition as defined above as a solvent, preferably in an agrochemical formulation, and more particularly to the use of a composition as defined above for the preparation of an agrochemical formulation.

[0201] Agrochemical formulations

[0202] The agrochemical formulation according to the present invention comprises:

[0203] a) at least one agricultural material,

[0204] b) a composition as described above,

[0205] c) optionally at least one emulsifier, preferably a surfactant, and

[0206] d) Optionally water.

[0207] "Agrochemical formulation" is intended to indicate a composition used in its concentrated form or diluted in water to a target use rate, which causes or provides a beneficial and / or useful effect in agriculture and / or provides biological activity in seeds, plants, soil, e.g., for seeds, for controlling pests and / or regulating the growth of plants and / or inducing defense responses in plants and / or enhancing metabolic and physiological processes in plants and soil. Agrochemical formulations are described, for example, in T. Tadros (ed.), Encyclopedia of Colloid and Interface Science, Springer-Verlag Berlin Heidelberg, 2013, pp. 3-80.

[0208] According to the present invention, an "agrochemical formulation" is a composition comprising the solvent composition according to the present invention and at least one agricultural material; optionally at least one emulsifier, preferably a surfactant, and optionally water.

[0209] As mentioned above, agriculture uses many agricultural materials. These are also called active plant protection products or active materials or active substances.

[0210] As used herein, the term "agricultural material" means an active ingredient that is particularly useful in agricultural practices, including cultivating soil for crop growth. However, the use of agricultural materials is not limited to application to crops. Agricultural materials can be applied to any surface, for example, for cleaning or to aid or inhibit the growth of living organisms. Other non-crop applications include, but are not limited to, application to animals, such as livestock, application to turf and ornamental plants, and application to railroad weeds.

[0211] Agricultural materials are generally products in pure or highly concentrated form, are generally insoluble in water and are known to those skilled in the art.

[0212] Depending on the water solubility of the agricultural material and its loading in the target formulation, identification of a suitable solvent to obtain a chemically and physically stable formulation can be very challenging.

[0213] Therefore, for agricultural materials with low or relatively low water solubility, it is of interest to use appropriate solvents to prepare concentrated liquid formulations. Such concentrated formulations of agricultural materials are usually diluted before agricultural use. Dilution by farmers is usually carried out by mixing the agrochemical formulation with water.

[0214] Preferably, at 20°C and atmospheric pressure (i.e., 1.013 x 10 5 Pa), the agricultural material is a water-insoluble agricultural material.

[0215] More preferably, the agricultural material is heated at 20°C and atmospheric pressure (i.e., 1.013 x 10 5 Pa) to no more than 100 g / L, even more preferably no more than 20 g / L, in particular no more than 5 g / L, for example no more than 1 g / L and even no more than 0.2 g / L.

[0216] Preferably, the agricultural material is selected from the group consisting of pesticides, nutrients, biostimulants, plant growth regulators, and mixtures thereof.

[0217] Advantageously, the agrochemical formulations according to the invention may comprise at least one pesticide.

[0218] For example, these pesticides may be selected from the group consisting of herbicides, fungicides, insecticides, acaricides, algaecides, molluscicides, acaricides, nematicides, biocides and rodenticides.

[0219] Those skilled in the art are familiar with such pesticides. Specific examples of pesticides can be found in the book “Sittig's handbook of Pesticides and Agricultural Chemicals”, 2nd edition, William Andrew Publishing, 2015.

[0220] The agrochemical formulations according to the invention may optionally comprise at least one nutrient.

[0221] Nutrients are chemical elements and compounds that are desirable or necessary to promote or improve plant growth. Nutrients are often described as either macronutrients or micronutrients.

[0222] Suitable nutrients for use in the agrochemical formulations according to the present invention may be micronutrient compounds, preferably those that are solid or partially soluble at room temperature (20°C).

[0223] Micronutrients typically refer to trace metals or trace elements and are usually administered in lower doses. Suitable micronutrients include trace elements selected from zinc, boron, chlorine, copper, iron, molybdenum and manganese.

[0224] The micronutrients may be in soluble form or contained as insoluble solids and may be in the form of salts or chelates.Preferably, the micronutrients are in the form of carbonates or oxides.

[0225] Preferably, the micronutrients may be selected from zinc, calcium, molybdenum or manganese, or magnesium. More preferably, the micronutrients used in the agrochemical formulations according to the present invention may be selected from zinc oxide, manganese carbonate, manganese oxide, or calcium carbonate.

[0226] The agrochemical formulation according to the present invention may further comprise at least one macronutrient.

[0227] Macronutrients typically refer to those containing nitrogen, phosphorus, and potassium, and include fertilizers such as ammonium sulfate and water conditioners. Suitable macronutrients include fertilizers and other nitrogen, phosphorus, or sulfur containing compounds and water conditioners.

[0228] Suitable fertilizers include inorganic fertilizers that provide nutrients such as nitrogen, phosphorus, potassium or sulfur. Examples of such fertilizers include:

[0229] For nitrogen as a nutrient: nitrates and or ammonium salts, such as ammonium nitrate, including in combination with urea, for example as urean-type materials, calcium ammonium nitrate, ammonium nitrate sulfate, ammonium phosphates (particularly monoammonium phosphate, diammonium phosphate and polyammonium phosphate), ammonium sulfate and, less commonly, calcium nitrate, sodium nitrate, potassium nitrate and ammonium chloride;

[0230] For phosphorus as a nutrient: acidic forms of phosphorus, such as phosphoric acid, pyrophosphoric acid or polyphosphoric acid, but more usually in the form of salts, such as ammonium phosphates (especially monoammonium phosphate, diammonium phosphate and ammonium polyphosphate), potassium phosphates (especially potassium dihydrogen phosphate and potassium polyphosphate);

[0231] For sulfur as a nutrient: ammonium sulfate and potassium sulfate, for example mixed with magnesium sulfate.

[0232] The agrochemical formulations according to the invention may optionally comprise at least one biostimulant.

[0233] The term "biostimulant" is preferably intended to mean a compound that can enhance a metabolic or physiological process such as respiration, photosynthesis, nucleic acid uptake, ion uptake, nutrient delivery, or a combination thereof.

[0234] Typically, this is a substance or microorganism that, when applied to the seed, plant, or rhizosphere, can stimulate natural processes to enhance or benefit nutrient uptake, nutrient use efficiency, tolerance to abiotic stress, or crop quality and yield.

[0235] Non-limiting examples of biostimulants include seaweed extracts (eg, ascophyllum nodosum), humic acid (eg, potassium humate), fulvic acid, inositol, glycine, and combinations thereof.

[0236] The agrochemical formulations according to the invention may optionally comprise at least one plant growth regulator.

[0237] Plant growth regulators refer to active ingredients 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-naphthylacetic acid, 1-naphthylacetic acid-salt, 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-naphthyloxyacetic acid, 2-naphthyloxyacetic acid sodium salt, 3-chloro-4-hydroxyphenylacetic acid, 3-indoleacetic acid, 4-biphenylacetic acid, 4-chlorophenoxyacetic acid (4-CPA), 4-hydroxyphenylacetic acid, 6-benzylaminopurine, auxindole, α-naphthylacetic acid K-salt, β-naphthyloxyacetic 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, indole-3-acetic acid methyl ester, naphthylacetamide, naphthylacetic acid (NAA), phenylacetic acid, picloram, potassium cyclohexaneate, sodium cyclohexaneate, 4-hydroxyphenylethanol, 4-CPPU, 6-benzylaminopurine (BA), 6-(Y,Y-dimethylallylamino)purine (2iP), 2-iP-2HCl, adenine, adenine hemisulfate, benzyl adenine, kinetin, cytokinin (meta-topolin), N6-benzoyl adenine, N-benzyl-9-(2-tetrahydropyranyl)adenine (BP A), N-(2-chloro-4-pyridyl)-N-phenylurea, gibberellic acid (GA3), gibberellins, gibberellins A4+A7 (GA n), ethylene and abscisic acid.

[0238] Several agricultural materials may be combined in one agrochemical formulation according to the invention.

[0239] Preferably, the amount of the one or more agricultural materials in the agrochemical formulation ranges from 0.01% to 90% by weight, more preferably from 0.1% to 80% by weight; even more preferably from 0.5% to 70% by weight; better still from 1% to 65% by weight, in particular from 5% to 60% by weight, and for example from 10% to 60% by weight, relative to the total weight of the agrochemical formulation.

[0240] According to the first embodiment of the present invention (concentrated composition), the total content of the one or more agricultural materials in the agrochemical formulation is in the range of 5% to 90% by weight, more preferably 5% to 70% by weight, even more preferably 5% to 60% by weight, and in particular 10% to 60% by weight relative to the total weight of the agrochemical formulation.

[0241] According to the second embodiment of the present invention (diluted composition), the total content of the one or more additional agricultural materials in the agrochemical formulation ranges from 0.01% to 3% by weight, more preferably from 0.05% to 2% by weight, and even more preferably from 0.1% to 1% by weight, relative to the total weight of the agrochemical formulation.

[0242] The agrochemical formulation according to the invention comprises a solvent composition as described previously.

[0243] Preferably, the solvent composition according to the invention comprises 10 to 99% by weight, more preferably 20 to 95% by weight, in particular 30 to 90% by weight, for example 30 to 80% by weight, relative to the total weight of the agrochemical formulation.

[0244] The agrochemical formulations according to the invention may optionally comprise at least one emulsifier.

[0245] Emulsifiers are agents 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.

[0246] Preferably, the agrochemical formulation according to the present invention further comprises at least one surfactant.

[0247] Advantageously, the surfactants that may be used in the present invention are selected from anionic, nonionic, cationic, amphoteric or zwitterionic surfactants, and mixtures thereof.

[0248] More preferably, the surfactant is selected from anionic surfactants, nonionic surfactants, and mixtures thereof.

[0249] Even better, the surfactant is selected from anionic surfactants, polyalkoxylated nonionic surfactants, and mixtures thereof.

[0250] The emulsifiers and surfactants that can be used vary from agricultural materials.

[0251] As examples of anionic surfactants, mention may be made without any intended restriction thereof:

[0252] - alkylsulfonic acids, arylsulfonic acids, which are optionally substituted by one or more hydrocarbon groups and whose acid functions are partially or completely salified, such as C8-C 50 Alkylsulfonic acid, more particularly C8-C 30 , preferably C 10 -C 22 Alkylsulfonic acid, benzenesulfonic acid, naphthalenesulfonic acid, which is 30 , preferably C4-C 16 Alkyl and / or C2-C 30 , preferably C4-C 16 Alkenyl substitution,

[0253] - monoesters or diesters of alkylsulfosuccinic acids, wherein the linear or branched alkyl moiety is optionally substituted by one or more linear or branched C2-C4 hydroxylated and / or alkoxylated (preferably ethoxylated, propoxylated, ethylpropoxylated) groups,

[0254] - phosphates, more particularly selected from those comprising at least one linear or branched, saturated, unsaturated or aromatic hydrocarbon radical, the hydrocarbon radical comprising 8 to 40, preferably 10 to 30 carbon atoms, optionally substituted by at least one alkoxylated (ethoxylated, propoxylated, ethylpropoxylated) group. In addition, they comprise at least one monoesterified or diestered phosphate group, making it possible to have one or two free or partially or completely salified groups. Preferred phosphates are the types of monoesters and diesters of the following items: phosphoric acid and alkoxylated (ethoxylated and / or propoxylated) mono-, di- or tri-phenylenediphenol, or alkoxylated (ethoxylated and / or propoxylated) mono-, di- or tri-alkylphenol, optionally substituted by one to four alkyl groups; phosphoric acid and alkoxylated (ethoxylated or ethylpropoxylated) C8-C 30 , preferably C 10 -C 22 Alcohols; phosphoric acid and non-alkoxylated C8-C 22 , preferably C 10 -C 22 alcohol,

[0255] - sulfates obtained from saturated or aromatic alcohols optionally substituted with one or more alkoxylated (ethoxylated, propoxylated, ethylpropoxylated) groups, and in which the sulfate function is present in the form of the free acid or is partially or completely neutralized. As examples, mention may be made more particularly of saturated or unsaturated C8-C 20 Sulfates obtained from polyols, which may contain 1 to 8 alkoxylated (ethoxylated, propoxylated, ethylpropoxylated) units; Sulfates obtained from polyalkoxylated phenols, which are substituted with 1 to 3 saturated or unsaturated C2-C 30Hydroxycarbonyl substituted, and wherein the number of alkoxylation units is comprised between 2 and 40; sulfates obtained from polyalkoxylated mono-, di- or tristyrylphenols wherein the number of alkoxylation units varies from 2 to 40.

[0256] Anionic surfactants can be in acid form (they are potentially anionic) or in partially or completely salted form with a counterion. The counterion can be an alkali metal (such as sodium or potassium), an alkaline earth metal (such as calcium), or even have the formula N(R)4 + The ammonium ion wherein the R groups are the same or different and represent a hydrogen atom or a C1-C4 alkyl group which is optionally substituted by an oxygen atom.

[0257] As examples of nonionic surfactants, mention may be made without any intended restriction thereof:

[0258] - polyalkoxylated (ethoxylated, propoxylated, ethylpropoxylated) phenols, which are 20 , preferably C4-C 12 The alkyl group is substituted or substituted by at least one alkaryl group, the alkyl portion of which is a C1-C6 alkyl group. More particularly, the total number of alkoxylated units is comprised between 2 and 100. As examples, mention may be made of polyalkoxylated mono-, di- or tri-(phenylethyl)phenols, or polyalkoxylated nonylphenols. Among the ethoxylated and / or propoxylated, sulfated and / or phosphated di- or tristyrylphenols, mention may be made of ethoxylated di-(phenyl-1-ethyl)phenol containing 10 ethylene oxide units; ethoxylated di-(phenyl-1-ethyl)phenol containing 7 ethylene oxide units; sulfated ethoxylated di-(phenyl-1-ethyl)phenol containing 7 ethylene oxide units; ethoxylated tris-(phenyl-1-ethyl)phenol containing 8 ethylene oxide units; ethoxylated tris-(phenyl-1-ethyl)phenol containing 16 ethylene oxide units; sulfated ethoxylated tris-(phenyl-1-ethyl)phenol containing 16 ethylene oxide units; ethoxylated tris-(phenyl-1-ethyl)phenol containing 20 ethylene oxide units; and phosphated ethoxylated tris-(phenyl-1-ethyl)phenol containing 16 ethylene oxide units.

[0259] -Polyalkoxylated (ethoxylated, propoxylated, ethylpropoxylated) C6-C 22 Fatty acids or alcohols. The number of alkoxylation units is comprised between 1 and 60. The term ethoxylated fatty acids includes both the products obtained by ethoxylation of fatty acids with ethylene oxide and those obtained by esterification of fatty acids with polyethylene glycol.

[0260] - polyalkoxylated (ethoxylated, propoxylated, ethylpropoxylated) triglycerides of plant or animal origin. Thus, triglycerides from lard, tallow, ground nut oil, butter, cottonseed oil, linseed oil, olive oil, palm oil, grapeseed oil, fish oil, soybean oil, castor oil, rapeseed oil, coconut shell oil (coprah oil), coconut oil may be included, and the total number of alkoxylated units included is between 1 and 60. The term ethoxylated triglycerides refers to both products obtained by ethoxylation of triglycerides with ethylene oxide and those obtained by transesterification of triglycerides with polyethylene glycol.

[0261] - sorbitan esters, which are optionally polyalkoxylated (ethoxylated, propoxylated, ethylpropoxylated), more particularly C 10 -C 20 Cyclic sorbitan esters of fatty acids such as lauric acid, stearic acid or oleic acid and comprising a total number of alkoxylated units comprised between 2 and 50.

[0262] Useful emulsifiers are especially the following products, all sold by Solvay:

[0263] - TSP / 724: Surfactant based on ethylpropoxylated tristyrylphenol,

[0264] - 796 / P: Surfactant based on ethylpropoxylated tristyrylphenol

[0265] - CY 8: Surfactant based on ethoxylated tristyrylphenol

[0266] - BSU: Surfactants based on ethoxylated tristyrylphenol

[0267] - S / 25: Surfactant based on ethoxylated tristyrylphenol

[0268] - 3D33: Surfactant based on ethoxylated tristyrylphenol phosphate

[0269] - RC: Surfactants based on ethoxylated castor oil

[0270] - OR / 36: Surfactants based on ethoxylated castor oil

[0271] - VO2003: Surfactants based on ethoxylated castor oil

[0272] - OL40: Surfactant based on ethoxylated sorbitan hexaoleate

[0273] - T / 20: Surfactant based on ethoxylated sorbitan esters.

[0274] - TBE724: Surfactant based on ethylpropoxylated tristyrylphenol

[0275] - TEB25: A blend of surfactants based on ethoxylated castor oil, calcium dodecylbenzenesulfonate, and alkoxylated polymers

[0276] - 60 / B: Surfactant based on dodecylbenzenesulfonate

[0277] - 60 / BE: Surfactant based on dodecylbenzenesulfonate.

[0278] Preferably, the total amount of the one or more emulsifiers in the agrochemical formulation according to the invention ranges from 0.05% to 40% by weight, more preferably from 0.1% to 35% by weight, even more preferably from 0.5% to 30% by weight, in particular from 1% to 25% by weight, and for example from 1% to 5% by weight, relative to the total weight of the agrochemical formulation.

[0279] Preferably, the total amount of one or more surfactants in the agrochemical formulations according to the invention ranges from 0.05% to 40% by weight, more preferably from 0.1% to 35% by weight, even more preferably from 0.5% to 30% by weight, in particular from 1% to 25% by weight, and for example from 1% to 5% by weight, relative to the total weight of the agrochemical formulation.

[0280] Preferably, the total amount of one or more anionic surfactants in the agrochemical formulations according to the invention ranges from 0.05% to 40% by weight, more preferably from 0.1% to 35% by weight, even more preferably from 0.5% to 30% by weight, in particular from 1% to 25% by weight, and for example from 1% to 5% by weight, relative to the total weight of the agrochemical formulation.

[0281] Preferably, the total amount of one or more nonionic surfactants, in particular one or more polyalkoxylated nonionic surfactants, in the agrochemical formulations according to the invention is in the range of 0.05 to 40% by weight, more preferably 0.1 to 35% by weight, even more preferably 0.5 to 30% by weight, in particular 1 to 25% by weight, and for example 1 to 5% by weight, relative to the total weight of the agrochemical formulation.

[0282] Advantageously, the agrochemical formulations according to the invention may further comprise at least one cosolvent.

[0283] According to the present invention, co-solvents may be used that are different from the first solvent, the second solvent and the further solvent as previously described.

[0284] These other solvents or cosolvents are preferably selected from:

[0285] - linear or branched, saturated or unsaturated aliphatic hydrocarbons, which may contain halogen atoms, phosphorus atoms, sulfur atoms and / or nitrogen atoms and / or functional groups,

[0286] - carbocyclic or heterocyclic hydrocarbons, any of which are saturated, unsaturated or aromatic, which may contain halogen atoms, phosphorus atoms, sulfur atoms and / or nitrogen atoms and / or functional groups,

[0287] More preferably, the co-solvent is selected from:

[0288] - alkanes, cycloalkanes and aromatic derivatives, for example paraffins with branched or straight chains such as "white oil" or decalin; mono-, di- or trialkylbenzenes or naphthalenes, sold under the trade names Compounds sold in 100, 150, 200 standard and ND grades;

[0289] aliphatic, cycloaliphatic or aromatic monoesters, diesters or triesters, for example alkyl alkanoates such as methyl oleate; benzyl alkanoate; alkyl benzoates; gamma-butyrolactone; caprolactone; esters of glycerol and citric acid; alkyl salicylates; phthalates; dibenzoates; acetoacetates; glycol ether acetates, dipropylene glycol diacetate;

[0290] - mono-, di- or tri-alkyl phosphates, such as, for example, triethyl phosphate; tributyl phosphate; or tri-2-ethylhexyl phosphate;

[0291] - aliphatic, cycloaliphatic or aromatic ketones, such as, for example, dialkyl ketones; benzyl ketone; fenchone; acetophenone; cyclohexanone; alkylcyclohexanone;

[0292] - aliphatic, cycloaliphatic or aromatic alcohols, such as, for example, diols; 2-ethylhexanol; cyclohexanol; benzyl alcohol; tetrahydrofurfuryl alcohol;

[0293] - aliphatic, cycloaliphatic or aromatic ethers, such as, for example, ethers of glycols, notably ethylene glycol and propylene glycol, and polymers thereof; diphenyl ether, diphenyl ether of dipropylene glycol; monomethyl ether or monobutyl ether, monobutyl ether of tripropylene glycol; alkoxyalkanols; dimethyl isosorbide;

[0294] - fatty acids, such as linoleic acid, linolenic acid, oleic acid;

[0295] - carbonates, such as, for example, propylene carbonate or butylene carbonate; lactates; fumarates, succinates, adipates, maleates;

[0296] - amides, such as, for example, alkyldimethylamides, dimethyl-decylamide;

[0297] -alkylurea;

[0298] - amines, such as, for example, alkanolamines, morpholine; N-alkyl-pyrrolidones;

[0299] -Tetramethyl sulfone;

[0300] -dimethyl sulfoxide;

[0301] - halogenated alkanes or halogenated aromatic solvents, such as, for example, chlorinated alkanes or chlorobenzene.

[0302] Crystallization inhibitors may also be present in the agrochemical formulations according to the invention. The crystallization inhibitors may be the cosolvents mentioned above. The crystallization inhibitors may also be non-polyalkoxylated fatty alcohols or fatty acids (for example the products sold by Solvay may be mentioned). OL700), alkanolamides, polymers, etc.

[0303] The agrochemical formulations according to the invention may further contain one or more additives different from the previously described ingredients, and these additives are preferably selected from viscosity regulators, suspending agents, antifoaming and defoaming agents (especially silicone antifoaming and defoaming agents), anti-rebound agents, anti-leaching agents, penetration aids, inert fillers (especially mineral fillers), binders, diluents, antifreeze agents, stabilizers, dyes, emetics, stickers (adhesion promoters), absorbents, dispersants, disintegrants, wetting agents, preservatives and / or antimicrobial agents.

[0304] Each additive may be present in the agrochemical composition according to the invention in an amount ranging from 0% to 20% by weight, more preferably from 0% to 10% by weight, relative to the total weight of the composition. Each additive may, for example, be present in the agrochemical formulation according to the invention in an amount ranging from 0.1% to 20% by weight, particularly from 0.1% to 10% by weight, relative to the total weight of the composition. Each additive may be present in the composition according to the invention in an amount preferably ranging from 0% to 5% by weight, particularly from 0.1% to 5% by weight, relative to the total weight of the composition. A person skilled in the art will be able to select these optional additives and their amounts so that they do not impair the properties of the agrochemical composition according to the invention.

[0305] Advantageously, the agrochemical formulations according to the present invention are effective at 20°C and atmospheric pressure (ie, 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 agricultural materials.

[0306] Depending on the agricultural material according to the invention, different types of formulations can be used. The formulations that can be used depend on the physical form of the agricultural material (eg solid or liquid) and their physicochemical properties in the presence of other compounds (such as water or solvents).

[0307] For practical reasons (e.g. for ease of handling), it may be preferred to use formulations in liquid form. Depending on the physicochemical properties of the different agricultural materials under consideration, the formulations may be in the form of emulsifiable concentrates (EC), concentrated emulsions in water (EW), microemulsions (ME), suspoemulsions (SE), oil dispersions (OD), dispersible concentrates (DC), suspension concentrates (SC), capsule suspensions (CS), soluble liquids (SL), flowable concentrates for seed treatment (FS).

[0308] Preferably, the agrochemical formulation according to the present invention is in the form of an emulsifiable concentrate (EC), a concentrated emulsion in water (EW), a microemulsion (ME), a suspoemulsion (SE), an oil dispersion (OD), a dispersible concentrate (DC), a capsule suspension (CS), or a soluble liquid (SL).

[0309] Even more preferably, the agrochemical formulation according to the invention is in the form of an emulsifiable concentrate, an aqueous emulsion concentrate, a microemulsion concentrate, a suspoemulsion concentrate, an oil dispersion concentrate or a dispersible concentrate.

[0310] Even better, the agrochemical formulations according to the invention are in the form of emulsifiable concentrates (EC).

[0311] In particular, it was noted that compositions comprising a solvent having general formula (B) and ethyl lactate instead of a first solvent having general formula (A) (outside the present invention) were difficult to formulate in the form of emulsifiable concentrates (EC); probably due to the high miscibility of ethyl lactate in water.

[0312] Agrochemical formulations according to the present invention are typically concentrated agrochemical formulations and are intended to be spread on cultivated fields or fields to be cultivated, most often spread after dilution with water, so as to obtain a diluted composition. Dilution is typically performed by a farm operator directly in a barrel ("tank mix"), for example, in a barrel of a device intended to spread the composition. This does not exclude the possibility that a farm operator adds other plant protection products such as fungicides, herbicides, pesticides, insecticides, fertilizers, adjuvants, etc. Therefore, the formulation can be used to prepare a formulation of agricultural material diluted in water by mixing at least one portion by weight of a concentrated formulation with at least 10 parts, preferably less than 10,000 parts of water. The dilution ratio and amount to be applied on the field typically depend on the agricultural material and the desired dosage (this can be determined by the farm operator) for treating the field.

[0313] According to one embodiment of the present invention, the agrochemical formulation according to the present invention is aqueous.

[0314] According to this embodiment, the water content of the agrochemical 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, in particular from 25% to 85% by weight, and for example from 25% to 70% by weight, relative to the total weight of the agrochemical formulation.

[0315] According to this embodiment, the pH range is preferably 1 to 11, and more preferably 2.5 to 9.5.

[0316] The pH of the composition can be adjusted to the desired value with the aid of an alkalizing agent or an acidifying agent. Among the alkalizing agents, one or more alkalizing agents such as ammonia, sodium hydroxide or ethanolamine can be used. Among the acidifying agents, inorganic or organic acids such as hydrochloric acid or orthophosphoric acid can be mentioned, for example.

[0317] According to a particular embodiment of the present invention, the agrochemical formulation may advantageously comprise:

[0318] a) 0.01 to 90% by weight, preferably 5 to 60% by weight, of at least one agricultural material, relative to the total weight of the agrochemical formulation,

[0319] b) 5 to 90% by weight, preferably 10 to 90% by weight, in particular 30 to 90% by weight, for example 30 to 80% by weight, of a solvent composition according to the invention, relative to the total weight of the agrochemical formulation,

[0320] c) 0.1% to 40% by weight, preferably 1% to 30% by weight, of at least one of said cosolvents, relative to the total weight of the agrochemical formulation,

[0321] d) 0.05 to 40% by weight, preferably 0.1 to 35% by weight, more preferably 0.5 to 30% by weight, in particular 1 to 25% by weight, for example 1 to 5% by weight, of at least one surfactant, relative to the total weight of the agrochemical formulation,

[0322] e) 5 to 90% by weight, preferably 10 to 80% by weight, in particular 25 to 70% by weight, of water, relative to the total weight of the agrochemical formulation.

[0323] The conventional methods known for preparing agrochemical formulations or solvent mixtures can be carried out. This can be achieved by simply mixing the components.

[0324] The agrochemical formulations according to the invention can be used for killing or suppressing harmful organisms and / or for eradicating undesirable vegetation and / or for suppressing the growth of undesirable vegetation.

[0325] The agrochemical formulations according to the present invention can be diluted and applied in a conventional manner to at least one plant, an area adjacent to a plant, soil suitable for supporting plant growth, the roots of a plant, the foliage of a plant, and / or seeds suitable for producing a plant; for example, by watering (drenching), drip irrigation, spraying, and / or atomization.

[0326] In the above description, all preferred embodiments concerning the components can be used alone or in combination.

[0327] The following examples serve to illustrate the present invention.

[0328] Examples

[0329] In the present examples, the term solvent system is a composition, and a single solvent or a blend of several solvents may be contemplated.

[0330] The term combination of actives is used to describe the association of several (at least two) different agricultural materials.

[0331] Determination of the maximum solubility of an active substance or combination of active substances in a solvent system

[0332] The maximum solubility of an active ingredient or combination of active ingredients in a solvent system is characterized by visual observation. At a given concentration, if the mixture is clear (to the naked eye), then the active ingredient(s) are considered soluble in the solvent system at that concentration. However, if one or more active ingredients precipitate, then it is no longer soluble in the solvent system and has reached its maximum solubility.

[0333] Thus, maximum solubility is defined as the maximum amount of active ingredient(s) that can be dissolved in a solvent system, equal to the amount at which the mixture remains clear (to the naked eye).

[0334] Test 1: Maximum Solubility - Description of the Test of Active Ingredient Alone (Sole) in a Solvent System

[0335] Each active ingredient or combination is added little by little to the different solvent systems. The solution is magnetically stirred until completely dissolved. Additional amounts of active ingredient are then added, and this process is repeated until the last portion of the added active ingredient is no longer soluble, carefully stirring the solution after each addition.

[0336] Test 2: Low Temperature Study - Description of the Test of Combinations of Actives

[0337] Mixtures were prepared by dissolving the active ingredient or combination of active ingredients at a specific concentration in different solvent systems. Each active ingredient was weighed individually and added to the solvent system. The following observations were then made:

[0338] - Visual observation at 25°C - Record the appearance of the mixture and investigate the possible presence of crystals.

[0339] - Visual observation at 0°C - The mixture was placed at 0°C for 7 days and the appearance of the mixture and the possible presence of crystals (CIPAC MT39 test) were recorded.

[0340] -Visual observation under nucleation at 0°C-Crystals of each active ingredient were introduced into the solution and allowed to nucleate at 0°C for 7 days. The mixture was stirred and placed again at 0°C for another 7 days for nucleation. The final identification of the aspect of the mixture and the presence of crystals (CIPAC MT39 test) were noted.

[0341] If the mixture (sole or combined solvent system of actives) forms a clear solution (a homogeneous liquid phase to the naked eye), the solvent system is considered a good system, whereas if a two-phase system is obtained (the presence of particles, sediments, crystals or a turbid solution), it indicates that the solvent system is a poor system.

[0342] Test 3: Stability after dilution ("emulsification")

[0343] The objective is to evaluate the emulsion stability of emulsions formed by dispersing an emulsifiable concentrate (EC) in water at a specified dilution rate (eg, 5% as shown below).

[0344] First, 95 wt% of water is poured into a 100 mL graduated cylinder. Then, 5 wt% of a mixture of at least one active ingredient and at least one surfactant dissolved in at least one solvent is added to the graduated cylinder.

[0345] The measuring cylinder was inverted 10 times continuously for emulsification, and then allowed to stand in a 30°C constant temperature bath for several hours.

[0346] The stability of the emulsions was then assessed in terms of the amount of free 'oil' and / or 'cream' which separated while the emulsions were allowed to sit undisturbed for 24 hours. Observations were made after 30 minutes, 2 hours and 24 hours.

[0347] The ability of the system to re-emulsify at the end of the 24 hour period was also determined by again inverting the cylinders 10 times in succession. The stability was then assessed 30 minutes and 2 hours after re-emulsification (adapted from the CIPAC MT 36.3 test).

[0348] Example 1: Dissolution of the active ingredient (sole) in the binary solvent system of the present invention

[0349] According to the above protocol, the reaction of prothioconazole, tebuconazole and azoxystrobin in GFbio ReSolv200 (as a comparative solvent system), The maximum solubility was in SL191 (as a comparative solvent system, having a Renewable Carbon Index (RCI) of 0.50) and Blend 1 (a solvent system according to the present invention, having an RCI of 0.55).

[0350] Blend 1 according to the invention consists of 73% by weight of GFbio ReSolv 200 (n-butyl levulinate) and 27% by weight of

[0351] SL191 (2,2-dimethyl-4-hydroxymethyl-1,3-dioxolane) composition.

[0352] The values ​​of maximum solubility (in g / 100 g solvent) are summarized in the table below:

[0353]

[0354] These data show that The solvent system of the present invention provided acceptable (for tebuconazole) or even improved (for prothioconazole and azoxystrobin) performance in terms of solubilization performance compared to SL191, while increasing the RCI (from 0.50 to 0.55).

[0355] Example 2: Dissolution of the active ingredient (sole) in the binary solvent system of the present invention

[0356] The following formulations were prepared according to the following scheme:

[0357] - Formulation A: 200 mg of prothioconazole was mixed with 800 μL of the solvent system. The solution was then magnetically stirred.

[0358] As in Example 1, blend 1 according to the invention consists of 73% by weight of GFbio ReSolv 200 and 27% by weight of SL191 composition.

[0359]

[0360]

[0361] RT: room temperature (25°C)

[0362] Formulation A highlights the ability of the solvent system of the present invention to dissolve prothioconazole.

[0363] Furthermore, inventive blend 1 advantageously exhibits a high RCI (0.55).

[0364] Example 3: Dissolution of the active ingredient (sole) in the solvent system of the present invention further containing an amide ester solvent

[0365] The maximum solubility of prothioconazole, tebuconazole, and azoxystrobin in Blend 1 and Blend 2 of Example 1 was measured according to the protocol described above.

[0366] Blend 2 according to the invention consists of 58% by weight of GFbio ReSolv 200, 11% by weight of SL191 and 31% by weight Polarclean (which contains methyl 5-(dimethylamino)-2-methyl-5-oxopentanoate).

[0367] The values ​​of maximum solubility (in g / 100 g solvent) are summarized in the table below:

[0368]

[0369] These data demonstrate that the solvent systems of the present invention (Blend 1 and Blend 2) yield improved performance in terms of solubilization performance for prothioconazole, tebuconazole, and azoxystrobin.

[0370] Example 4: Active ingredient (sole) in a solvent system of the present invention further containing a cycloalkanone-based solvent Dissolution

[0371] The maximum solubility of difenoconazole, picoxystrobin, and azoxystrobin in Blend 1 (with an RCI of 0.55) and Blend 3 (with an RCI of 0.66) of Example 1 were measured according to the protocol described above.

[0372] Blend 3 according to the invention consists of 66% by weight of GFbio ReSolv 200, 10% by weight of SL191 and 24% by weight (dihydro-levulinic acid ketone) composition.

[0373] The values ​​of maximum solubility (in g / 100 g solvent) are summarized in the table below:

[0374]

[0375] These data demonstrate that the solvent systems of the present invention (Blend 1 and Blend 3) yield good performance in solubilization while further having high RCI (0.55 and 0.66, respectively).

[0376] Example 5: Active ingredient (combination) in a solvent system of the present invention further containing a cycloalkanone-based solvent Dissolution

[0377] 5.1 Prepare the following formulations according to the following scheme:

[0378] Formulation B: 11.8 wt% of prothioconazole was first added to the solvent system. 9.9 wt% of picoxystrobin was then added to the mixture, which was magnetically stirred.

[0379] Formulation C: 5.0 wt% of azoxystrobin was first added to the solvent system. 9.0 wt% of tebuconazole was then added to the mixture, and finally 18.0 wt% of prochloraz was added. The solution was then magnetically stirred.

[0380] As in Example 4, blend 3 according to the invention consists of 66% by weight of GFbio ReSolv 200, 10% by weight of SL191 and 24% by weight (dihydro-levulinic acid ketone) composition.

[0381] Characterization was performed according to the above method.

[0382]

[0383] RT: room temperature (25°C)

[0384] These two formulations highlight the ability of the solvent system of the present invention to dissolve challenging combinations of active ingredients.

[0385] These formulations remained stable at 0°C for 2 weeks, even with an additional nucleation step during the final 7 days.

[0386] Furthermore, inventive blend 3 advantageously exhibits a high RCI (0.66).

[0387] 5.2 The following formulations D and E were also prepared according to the following scheme:

[0388] Formulation D: 75 mg of azoxystrobin and 125 mg of prothioconazole were mixed with 800 μL of the solvent system. The solution was then magnetically stirred;

[0389] - Formulation E: 100 mg of azoxystrobin and 150 mg of prothioconazole were mixed with 750 μL of the solvent system. The solution was then magnetically stirred.

[0390] Characterization was performed according to the above method.

[0391]

[0392] RT: room temperature (25°C)

[0393]

[0394] RT: room temperature (25°C)

[0395] These formulations highlight the ability of the solvent system of the present invention to dissolve challenging combinations of active ingredients.

[0396] These formulations remained stable at 0°C for 2 weeks, even with an additional nucleation step during the final 7 days.

[0397] Example 6: Dissolution of active ingredient (combination) in the solvent system of the present invention further containing an amide ester solvent

[0398] Formulations B and C were prepared as described in Example 5.

[0399] As in Example 3, blend 2 according to the invention consists of 58% by weight of GFbio ReSolv 200, 11% by weight of SL191 and 31% by weight Polarclean composition.

[0400] Characterization was performed according to the above method.

[0401]

[0402] RT: room temperature (25°C)

[0403] These formulations highlight the ability of the solvent system of the present invention to dissolve challenging combinations of active ingredients.

[0404] These formulations remained stable at 0°C for 2 weeks, even with an additional nucleation step during the final 7 days.

[0405] Example 7: Dissolution of the active ingredient (sole) in the binary solvent system of the present invention

[0406] The following Formulation F was prepared according to the following scheme:

[0407] - Formulation F: 200 mg of prothioconazole was mixed with 800 μL of the solvent system. The solution was then magnetically stirred.

[0408] Blend 4 (outside the present invention) consisted of 75% by weight of GFbio ReSolv100 (ethyl levulinate, formerly named NXT SOLV 100 by GF Biochemicals) and 25% by weight of SL191 composition.

[0409] Blend 5 according to the invention consists of 75% by weight of GFbio ReSolv 200 and 25% by weight of SL191 composition.

[0410]

[0411] RT: room temperature (25°C)

[0412] Formulation F highlights the ability of Blend 5 (the solvent system of the present invention) to dissolve prothioconazole.

[0413] In particular, it appears that blend 5 according to the invention makes it possible to obtain better results than comparative blend 4.

Claims

1. A composition comprising: (i) 35% to 95% by weight, relative to the total weight of the composition, of at least one first solvent of general formula (A): wherein R represents a linear or branched (C3-C6) alkyl group; and (ii) at least one second solvent having the general formula (C): in, - R1 and R2 are independently linear or branched C1-C 12 Alkyl, C4-C 12 Cycloalkyl or aryl, -R3 is H, linear or branched (C1-C6) alkyl, (C3-C8) cycloalkyl, or a -C(O)R4 group, wherein R4 is linear or branched C1-C4 alkyl or C5-C6 cycloalkyl.

2. The composition according to claim 1, wherein In formula (A), R represents a linear (C4-C6) alkyl group; more preferably, the first solvent is butyl levulinate.

3. A composition according to any one of the preceding claims, wherein The total amount of the first solvent ranges from 35% to 90% by weight, more preferably from 35% to 85% by weight, even more preferably from 35% to 80% by weight, and in particular from 50% to 80% by weight relative to the total weight of the composition.

4. A composition according to any one of the preceding claims, wherein In formula (C): - R1 and R2 are independently linear or branched (C1-C 12 )alkyl, and / or - R3 is H or linear or branched (C1-C6) alkyl; Preferably, R1 and R2 are independently of each other linear or branched (C1-C4) alkyl, and R3 is H; and more preferably, R1 and R2 are methyl and R3 is H.

5. A composition according to any one of the preceding claims, wherein The total amount of the second solvent ranges from 1% to 50% by weight, preferably from 1% to 45% by weight, more preferably from 2% to 40% by weight, in particular from 5% to 35% by weight relative to the total weight of the composition.

6. A composition according to any one of the preceding claims, wherein The weight ratio of the total content of the one or more first solvents to the total content of the one or more second solvents ranges from 0.1 to 20; preferably 0.5 to 15; more preferably 1 to 15; even more preferably 1 to 10; especially 1 to 8; and for example 1.5 to 7.

5.

7. The composition according to any one of the preceding claims, further comprising one or more additional solvents, preferably selected from: -amide ester solvent, - amide solvent, - a solvent selected from levoglucosone, dihydrolevoglucosone or a derivative thereof, - an aromatic solvent other than the solvent of formula (A) or (C), - an ester or diester solvent other than the solvent of formula (A), - an alkyl acetate solvent other than the solvent of formula (A), - sulfoxide solvent, and - mixtures thereof, Preferably, it is selected from amide ester solvents, amide solvents and mixtures thereof.

8. The composition according to any one of the preceding claims, further comprising at least one amide ester solvent having formula (B): R 1 CONR 2 R 3 (B) in: -R 1 is a linear or branched saturated aliphatic group having 1 to 6 carbon atoms, substituted by one or more functional groups selected from -OH groups and / or -COOR' groups, wherein R' is a (C1-C6)alkyl group, -R 2 and R 3 are the same or different, are (C1-C6) alkyl, R 1 and R 2 or R 3 The rings may together form a ring containing 4 to 6 carbon atoms and may be optionally substituted by one or more (C1-C4)alkyl groups and / or one or more groups selected from -OH groups, -OR' groups, -COOR' groups and -CONR 4 R 5 The functional group of the group is substituted, wherein R' is (C1-C6) alkyl, and R 4 and R 5 are the same or different, indicating a (C1-C6) alkyl group.

9. The composition according to any one of the preceding claims, further comprising at least one amide solvent of formula (D) different from those of formula (B): R”-CONR2R3(D) in: -R" is a straight chain or branched chain (C3-C 19 ) alkyl, preferably linear or branched (C7-C 19 )alkyl, more preferably a straight chain alkyl containing 7, 8 or 9 carbon atoms, and even more preferably a straight chain (C9)alkyl, and - R2 and R3, which may be identical or different, indicate a hydrogen atom or a (C1-C6)alkyl group, preferably a (C1-C4)alkyl group, more preferably a (C1-C2)alkyl group, and even better a methyl group, The premise is that if R 2 is a hydrogen atom, then R 3 It is a (C1-C6) alkyl group.

10. The composition according to any one of the preceding claims, further comprising at least one solvent selected from levoglucosone, dihydrolevoglucosone or derivatives thereof; preferably, the composition comprises dihydrolevoglucosone.

11. Use of the composition according to any one of claims 1 to 10 for the preparation of an agrochemical formulation.

12. Use of the composition according to any one of claims 1 to 10 as solvent, in particular in agrochemical formulations.

13. An agrochemical formulation comprising: a) at least one agricultural material, b) a composition according to any one of claims 1 to 10, c) optionally at least one emulsifier, preferably a surfactant, and d) Optionally water.

14. The formulation according to the preceding claim, in the form of an emulsifiable concentrate, an emulsion in water concentrate, a microemulsion concentrate, a suspoemulsion concentrate, an oil dispersion concentrate or a dispersible concentrate; preferably an emulsifiable concentrate.

15. The formulation according to any one of claims 13 or 14, wherein The composition b) represents 10 to 99% by weight, preferably 20 to 95% by weight, in particular 30 to 90% by weight, for example 30 to 80% by weight, relative to the total weight of the agrochemical formulation.

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