CN120659535A

CN120659535A - Solvent composition for agrochemical formulations

Info

Publication number: CN120659535A
Application number: CN202480011456.XA
Authority: CN
Inventors: R·塔德莫里; V·古萨德; M·阿达米
Original assignee: French Special Operations Co
Current assignee: French Special Operations Co
Priority date: 2023-02-09
Filing date: 2024-02-08
Publication date: 2025-09-16
Also published as: WO2024165680A1; EP4661668A1

Abstract

The present invention relates to a solvent composition comprising at least one specific levulinate 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 the preparation of agrochemical formulations and to the agrochemical formulations themselves.

Description

Solvent composition for agrochemical formulations

The present invention relates to a solvent composition comprising at least one specific levulinate 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 the preparation of agrochemical formulations and to the agrochemical formulations themselves.

Agriculture uses many agricultural materials, such as fertilizers or pesticides, for example insecticides, herbicides or fungicides. They are also referred to as active plant protection products or active materials or active substances. Agricultural materials are generally products in pure or highly concentrated form.

Typically, agricultural materials are not used as pure substances, but they are typically formulated with other ingredients depending on the application area and the desired physical constitution of the form of use.

Regardless of the type of formulation and whether the formulation comprises one or more agricultural materials, in particular in the agricultural sector, attempts are made to achieve as high a concentration of agricultural material as possible for the respective formulation, since high concentrations of agricultural material allow to reduce the volume to be applied and thus lead to savings with respect to the auxiliary materials applied and with respect to packaging and logistics. Thus, in principle, highly concentrated stable formulations and co-formulations with environmentally friendly adjuvants are interesting.

Typically, such formulations comprise a combination of different agricultural materials rather than separate agricultural materials, so as to take advantage of the characteristics of the separate agricultural materials together at the time of application, or because the separate agricultural materials combine to have a synergistic effect, i.e., produce a superadditive increase in activity.

In the application of products for agricultural use, it is known to combine two or more agricultural materials having different mechanisms of action and/or different biological targets to widen the range of action of the mixture relative to those in the agricultural materials used alone, and for example to prevent the occurrence of resistance phenomena from harmful organisms or species which over time tend to reduce the effectiveness of the pesticide product used.

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

For agricultural materials having low or relatively low water solubility, the use of suitable 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. Further details regarding the definition of the above formulation can be found in the "guidelines file (Guidance document for the generation of data on the physical,chemical and technical properties of plant protection products)" for generating data on the physical, chemical and technical characteristics of plant protection products according to the european union's meeting and the council's regulations (EC) No. 1107/2009 on putting plant protection products on the market".

Such concentrated formulations of agricultural materials are typically diluted prior to agricultural use. Dilution by farmers is usually done by mixing agrochemical formulations with water.

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

Furthermore, agrochemical formulations generally comprise compounds which are able to obtain these physical forms. They may 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 costs and/or any damage to the environment.

In addition, certain solid agricultural materials are often difficult to formulate. For certain agricultural materials, it is difficult to produce concentrated formulations that are easily diluted by farmers, stable and without substantial drawbacks (actual or perceived drawbacks) with regard to safety, toxicity and/or ecotoxicity. For certain agricultural materials, it is difficult to formulate at relatively high concentrations with sufficient stability. In particular, it is necessary to avoid the occurrence of crystals, in particular at low temperatures and/or during dilution and/or during storage of the diluted composition, in particular during storage at low temperatures. Crystals can have deleterious effects, particularly clogging filters of devices used to spread diluted compositions, clogging spray devices, reducing the overall activity of the formulation, creating unnecessary problems with waste management procedures used to remove crystals, and/or causing maldistribution of one or more agricultural materials over the farmland.

The use of solvent systems based on a single solvent such as N-methylpyrrolidone (NMP) is known. Such a solvent is capable of dissolving a large quantity of agricultural material and avoiding the formation of crystals, but it is also dangerous, especially for the operator and the user handling it.

The agrochemical industry is looking for new solvent compositions having satisfactory properties for agricultural applications, like for example good dissolution 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 advantageous toxicological and/or ecotoxicological characteristics, 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 regenerability.

Thus, there is a continuing need to provide solvent systems for agricultural use that:

having a large modularity, i.e. the ability to be used for a large quantity of agricultural material,

Has the potential to dissolve significant amounts of agricultural materials,

Having a high compatibility with several agricultural materials combined together, for example in order to be able to achieve an enhanced biological efficacy,

Avoiding the appearance of crystals, even under severe conditions, and/or

Exhibiting good safety and sustainability characteristics, no risk classification and/or ecotoxicology or low risk classification and/or ecotoxicology,

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

Preferably, the solvent system should also have good inherent or readily biodegradability and a high renewable carbon index (degree of recycling).

These objects are achieved by the present invention, which is a composition comprising:

(i) 35% to 95% by weight, relative to the total weight of the composition, of at least one first solvent having the general formula (a):

wherein R represents a linear or branched (C ₃-C₆) alkyl group, and

(Ii) At least one second solvent having the general formula (C):

Wherein, the

R ₁ and R ₂ are each independently of the other straight-chain or branched C ₁-C₁₂ alkyl, C ₄-C₁₂ cycloalkyl or aryl,

-R ₃ is H, straight or branched (C ₁-C₆) alkyl, (C ₃-C₈) cycloalkyl, or

-A C (O) R ₄ group, wherein R ₄ is a linear or branched C ₁-C₄ alkyl or C ₅-C₆ cycloalkyl group.

The solvent composition according to the present invention has a large dissolution efficiency. In particular, the composition according to the invention preferably exhibits good modularity, good potential for dissolving significant amounts of agricultural materials, and high compatibility with several agricultural materials combined together, for example, in order to be able to achieve enhanced biological efficacy. It should be noted that the potential for dissolution of the solvent composition according to the invention is even better for agricultural materials, in addition to N- (N-butyl) -thiophosphoric triamide (NBPT).

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

Furthermore, it has been noted that the composition according to the invention can preferably guarantee good properties upon dilution, even for high loading formulations, and avoid/delay the appearance of crystals, even under severe conditions.

Furthermore, the composition according to the invention exhibits good safety and sustainability characteristics, advantageously without risk classification and ecotoxicology or with low risk classification and ecotoxicology.

In particular, the solvent composition according to the invention preferably has good (intrinsic or easy) biodegradability, or high final aerobic biodegradability in soil, and may generally exhibit a high renewable carbon index.

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 component or product.

The subject of the invention is also the use of the composition according to the invention for the preparation of agrochemical formulations.

The subject of the invention is also the use of the composition according to the invention as solvent, in particular in agrochemical formulations.

The subject of the invention is also an agrochemical formulation comprising at least one agrochemical material and a solvent composition according to the invention.

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 thus the transport costs thereof), it is particularly advantageous to use concentrated formulations, which are then usually diluted to the desired concentration by the end user.

Other features, aspects, and advantages of the present invention will become more apparent upon reading the following specification and examples.

In this specification, and unless otherwise indicated,:

the expression "at least one" is equivalent to the expression "one or more" and can be replaced by it;

The expression "between" is equivalent to the expression "range of" (from) and can be replaced by it, and is meant to include the limit value;

For the purposes of the present invention, the expression "greater than" and, correspondingly, the expression "less than" is intended to mean strictly greater than, and, correspondingly, strictly less than, the open range, and therefore does not include the limit value;

The expression "alkyl" refers to an acyclic, linear or branched alkyl group having the general formula C _nH_2n+1.

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

First solvent

The composition according to the invention comprises at least one first solvent having the general formula (a):

Wherein R represents a linear or branched (C ₃-C₆) alkyl group.

The first solvent having the general formula (a) is an ester of levulinic acid.

The radical R in formula (A) represents a linear or branched alkyl radical having at least 3 carbon atoms.

More preferably, the group R in formula (a) represents a linear (C ₃-C₆) alkyl group.

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 (C ₄-C₆) alkyl group, and more in particular a linear (C ₄-C₆) alkyl group.

Advantageously, the first solvent is butyl levulinate (i.e. R is a linear or branched C ₄ -alkyl group), and more particularly n-butyl levulinate (i.e. R is n-butyl), which is advantageously completely immiscible in water (which is preferred, for example, to formulate agrochemical formulations in emulsifiable concentrates) except for being of biological origin.

Among the 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 (Sigma Aldrich) and preferably GFbio ReSolv (butyl levulinate) sold by GF Biochemicals (GF Biochemicals) (previously named NXT SOLV 200).

Preferably, the total amount of the one or more first solvents having the general formula (a) 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.

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.

Renewable carbon is generally required to avoid or replace all carbon sources using any additional stone carbon from the ground. The renewable carbon may be from a biosphere, an atmospheric circle, or a technical circle, but not from a ground circle.

Renewable carbon is defined herein as carbon derived from newly surviving plant or animal organisms (as opposed to carbon derived from coal, oil or petroleum based fossil carbon), as well as carbon derived from CO ₂ capture.

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 whole molecule. For example, if 80% of the number of carbons present in the first solvent is renewable carbons, the RCI is 0.8.

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

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.

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

Second solvent

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

Wherein, the

-R ₃ is H, a linear or branched (C ₁-C₆) alkyl, (C ₃-C₈) cycloalkyl, or a-C (O) R ₄ group, wherein R ₄ is a linear or branched C ₁-C₄ alkyl or C ₅-C₆ cycloalkyl;

In a preferred embodiment:

R ₁ and R ₂ are each independently of the other a linear or branched (C ₁-C₁₂) alkyl radical, and/or

-R ₃ is H or a linear or branched (C ₁-C₆) alkyl group.

More preferably, according to this embodiment, R ₁ and R ₂ are independently of each other straight or branched (C ₁-C₄) alkyl and R ₃ is H.

In another preferred embodiment, R ₁ and R ₂ are independently selected from the group consisting of methyl, ethyl, isopropyl, n-propyl, isobutyl, n-butyl, t-butyl, n-pentyl, cyclopentyl, cyclohexyl, or phenyl, and more preferably methyl.

Advantageously, in formula (C) above, R ₃ is H or a-C (O) R ₄ group, wherein R ₄ is methyl, ethyl, isopropyl, n-propyl, isobutyl, n-butyl or tert-butyl. More preferably, R ₃ is H.

A very preferred embodiment is when R ₁ and R ₂ are methyl and R ₃ indicates a hydrogen atom. Corresponding commercial compounds are, for exampleLi-Tec 2V(SL 191) or solkeyal. The compound can be synthesized by a reaction between glycerol and acetone under well-known classical conditions. Glycerol may be obtained, for example, as a by-product of biodiesel production during transesterification of triglycerides.

One example is that R ₁ and R ₂ are methyl and R ₃ is a-C (O) R ₄ group, wherein R ₄ is methyl. The corresponding commercial compounds can be synthesized by transesterification of Solketal with alkyl acetate under well known classical conditions.

In another embodiment, R ₁ is methyl, R ₂ is isobutyl and R ₃ is H. The corresponding commercial compounds can be synthesized under well known classical conditions by reaction between glycerol and methyl isobutyl ketone.

In another specific embodiment, R ₁ is methyl, R ₂ is phenyl and R ₃ is H. The corresponding compounds can be synthesized by reaction between glycerol and acetophenone under well known classical conditions.

According to particular embodiments, the compound having formula (C) may be a biobased compound.

According to another particular embodiment, the at least one second solvent comprises a compound having formula (C) and a compound having formula (C'), wherein R ₁、R₂ and R ₃ have the same meaning as for formula (C).

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

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.

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.

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

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

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, still more preferably from 1 to 10, in particular from 1 to 8, and for example from 1.5 to 7.5.

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.

Additional solvent

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

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

More preferably, the additional solvent that can be used in the composition according to the invention is selected from:

an amide ester solvent, which is a solvent,

An amide solvent, which is a solvent selected from the group consisting of,

A solvent selected from the group consisting of levoglucosenone, dihydrolevoglucosenone or derivatives thereof,

An aromatic solvent different from the solvent having the general formula (A) or (C),

An ester or diester solvent different from the solvent having the general formula (A),

Alkyl acetate solvents which are different from the solvents of the general formula (A),

-Sulfoxide solvent, and

-Mixtures thereof.

Even more preferably, the additional solvent that may be used in the composition according to the invention is selected from the group consisting of amide ester solvents, amide solvents and mixtures thereof.

The amide ester solvent that can be used in the composition according to the invention is preferably selected from amide ester solvents having formula (B):

R¹CONR²R³(B)

Wherein:

R ¹ is a straight-chain or branched saturated aliphatic radical having from 1 to 6 carbon atoms, which is substituted by one or more functional groups selected from the group consisting of-OH groups and/or-COOR 'groups, wherein R' is (C ₁-C₆) alkyl, in particular (C ₁-C₄) alkyl, and more in particular (C ₁-C₂) alkyl,

R ² and R ³, which are identical or different, are (C ₁-C₆) alkyl, in particular (C ₁-C₄) alkyl, and more in particular (C ₁-C₂) alkyl,

-R ¹ and R ² OR R ³ together may form a ring containing 4 to 6 carbon atoms and optionally substituted with one OR more (C ₁-C₄) alkyl groups and/OR one OR more functional groups selected from-OH groups, -OR ' groups, -COOR ' groups and-CONR ⁴R⁵ groups, wherein R ' is (C ₁-C₆) alkyl, in particular (C ₁-C₄) alkyl, and more particularly (C ₁-C₂) alkyl, and R ⁴ and R ⁵ are the same OR different, indicating (C ₁-C₆) alkyl, in particular (C ₁-C₄) alkyl, and more particularly (C ₁-C₂) alkyl.

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

More preferably, Z is a straight or branched divalent alkylene group containing 4 carbon atoms, and even more preferably, Z is a branched divalent alkylene group containing 4 carbon atoms.

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

R’OOC-Z-CONR₂R₃(B’)

Wherein, the

Z is a divalent (C ₁-C₆) alkylene group, preferably (C ₂-C₅) alkylene group, more preferably (C ₄) alkylene group, and

R', R ₂ and R ₃ are identical or different and indicate (C ₁-C₆) alkyl, preferably (C ₁-C₄) alkyl, more preferably (C ₁-C₂) alkyl, and even better methyl.

Preferably, according to this embodiment, Z in formula (B') is a divalent (C ₄) alkylene group, more preferably a divalent alkylene-CH (CH ₃)-CH₂-CH₂) having the formula.

Preferably, according to this embodiment, R', R ₂ and R ₃ are (C ₁-C₄) alkyl, in particular methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, tert-butyl. And more preferably R', R ₂ and R ₃ are identical and especially (C ₁-C₂) alkyl. More advantageously, R', R ₂ and R ₃ are identical and indicate methyl.

Preferably, the one or more amide ester solvents are selected from compounds having formula (B '), wherein Z is (C ₄) alkylene, and R', R ₂ and R ₃ are methyl. Very preferably, the ester-amide solvent comprises at least one compound having the formula (B '), wherein Z is an alkylene group having the formula-CH (CH ₃)-CH₂-CH₂), and R', R ₂ and R ₃ are methyl groups.

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

Sold by Solvi CoPolarclean are examples of very suitable commercial solvents that can be used as further solvents according to the invention.

Preferably, the total amount of the one or more amide ester solvents having the 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.

Preferably, the total amount of the one or more amide ester solvents having the 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.

Preferably, the total amount of 5- (dimethylamino) -2-methyl-5-oxopentanoic acid methyl ester 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 still from 10% to 40% by weight, for example from 20% to 40% by weight, relative to the total weight of the composition.

The amide solvent that can be used in the composition according to the invention is different from the solvent having general formula (B) as defined above and is preferably selected from amide solvents having formula (D):

R”-CONR₂R₃(D)

Wherein R "is a linear or branched (C ₃-C₁₉) alkyl group, preferably a linear or branched (C ₇-C₁₉) alkyl group, more preferably a linear alkyl group comprising 7, 8 or 9 carbon atoms, and even more preferably a linear (C ₉) alkyl group, and R ₂ and R ₃ may be the same or different, indicating a hydrogen atom or a (C ₁-C₆) alkyl group, preferably a (C ₁-C₄) alkyl group, more preferably a (C ₁-C₂) alkyl group, and in particular a methyl group, provided that if R ₂ is a hydrogen atom, R ₃ is a (C ₁-C₆) alkyl group.

According to a preferred embodiment, R ₂ and R ₃ are identical.

According to another preferred embodiment, R "is a linear alkyl group comprising 7,8 or 9 carbon atoms, and R ₂ and R ₃ are the same and indicate (C ₁-C₂) alkyl.

More preferably, the amide solvent is N, N-dimethyldecanoamide, i.e., where R "is a linear (C ₉) alkyl group, and R ₂ and R ₃ are methyl groups (as sold, for example, by the sorvi companyADMA 10)。

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

Preferably, the total amount of amide solvents having 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.

Preferably, the total amount of N, N-dimethyldecanoamide 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.

Additional solvents that may be used in the composition according to the invention may be selected from the group consisting of levoglucosone, dihydrolevoglucosone or derivatives thereof.

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

The levoglucosenone having the formula C ₆H₆O₃ is ((1 s,5 r) -6, 8-dioxabicyclo [3.2.1] oct-2-en-4-one) of the following formula (I):

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

Typically, the derivative of levoglucosenone is a compound that can be synthesized directly and/or indirectly from levoglucosone. In other words, the levoglucosenone may be a starting material and/or an intermediate material for the synthesis of the levoglucosone derivative.

Dihydro-l-glucosone is derived from l-glucosone by hydrogenation of l-glucosone (e.g. over a supported palladium catalyst). Commercially, dihydrol-glucosone is available from Circa Group Pty Ltd(RTM) is available.

Dihydro-l-glucosone is a chiral dipolar aprotic solvent. The dihydrol-glucosone having the formula C ₆H₈O₃ is ((1S, 5R) -6, 8-dioxabicyclo [3.2.1] oct-4-one) having the formula (II):

As derivatives of dihydrol-glucosone, there may be mentioned ketal derivatives of dihydrol-glucosone, in particular cygnet 0.0.0 (spiro [6, 8-dioxabicyclo [3.2.1] octane-4, 2' - [1,3] dioxolane ]), cygnet 1.0.0, cygnet 1.1.1, cygnet 2.0.0, cygnet 4.0.0 (as described in "Intelligent approach to solvent substitution:the identification of a new class of levoglucosenone derivatives[ Smart solvent substitution methods: identification of a novel class of L-glucosone derivatives ] -Ana Alves Costa Pacheco et al-ChemSusChem [ chemical sustainable chemistry ],2016,9,3503-3512).

According to a specific embodiment, the composition according to the invention further comprises an additional solvent selected from the group consisting of levoglucosone, dihydrolevoglucosone, derivatives thereof, and mixtures thereof, preferably selected from the group consisting of levoglucosone, dihydrolevoglucosone, and mixtures thereof.

According to a particularly preferred embodiment, the composition according to the invention further comprises dihydrol-glucosone.

Preferably, the total amount of levoglucosenone, dihydrolevoglucosenone and derivatives thereof, when present in the composition, 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.

Preferably, the total amount of dihydrol-glucosone 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.

The aromatic solvents which can be used in the composition according to the invention are different from the solvents of general formula (a) or (B) as defined above.

Among the aromatic solvents, mention may be made of toluene, xylene and mixtures of C ₈-C₁₂ di-and tri-alkylbenzenes like

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.

Most of these hydrocarbons are obtained by fractionation of crude oil, and generally have a distillation range including about 135 ℃ to about 305 ℃, with those having a distillation temperature of about 183 ℃ to about 290 ℃ being preferred.

Among the aromatic hydrocarbons, commercial products of Nisseki Hisol SAS-296 (a mixture of 1-phenyl-1-xylylethane and 1-phenyl-1-ethylphenylethane, new Japanese Petroleum Co., ltd. (Nippon Oil Corporation)), cactus Solvent HP-MN (methylnaphthalene 80%, japanese energy Co., ltd. (Japan Energy Corporation)), cactus Solvent HP-DMN (dimethylnaphthalene 80%, japanese energy Co., ltd.), cactus Solvent P-100 (alkylbenzene having 9 to 10 carbon atoms, japanese energy Co., ltd.), cactus Solvent P-150 (alkylbenzene, japanese energy Co., ltd.), cactus Solvent P-180 (a mixture of methylnaphthalene and dimethylnaphthalene, japanese energy Co., ltd.), cactus Solvent P-200 (a mixture of methylnaphthalene and dimethylnaphthalene, japanese energy Co., ltd.), cactus Solvent P-220 (a mixture of methylnaphthalene and dimethylnaphthalene, japanese energy Co., ltd.), cactus Solvent PAD-1-dimethylnaphthalene, mononaphthalene may also be mentioned,100 (Aromatic hydrocarbon, ekkimex Mobil (Exxon Mobil Corporation))150 (Aromatic hydrocarbon, exxonMobil Co.) Co., ltd,200 (Aromatic hydrocarbon, exxon Mobil Co.), ultra-Low Naphtalene Aromatic150 (Exxon Mobil chemical Co., ltd. (ExxonMobil Chemical Company)), ultra Low Naphtalene Aromatic 200 (Exxon Mobil chemical Co., ltd.)150ND (aromatic hydrocarbon, exxon Mobil Co.),200ND (aromatic hydrocarbons, ekken Mobil), swasol 100 (toluene, wash petrochemical Co., ltd. (Maruzen Petrochemical Co Ltd)) and Swasol 200 (xylene, wash petrochemical Co., ltd.).

Mixtures of C ₈-C₁₂ di-and tri-alkylbenzenes having a flash point of at least 60.5℃may be mentioned in particular.

Such mixtures are commercially available, in particular from the company Exxon Mobil under the name150 And200 Are commercially available.

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

Preferably, the total amount of aromatic solvents other than the solvents 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.

Preferably, the total amount of C ₈-C₁₂ 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, in particular from 10% to 30% by weight, relative to the total weight of the composition.

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.

The ester or diester solvents that can be used as further solvents in the composition according to the invention are different from the solvents having the general formula (a) or (C) as defined above.

Among the ester or diester solvents, mention may be made of 2-ethylhexyl lactate, alkyl acetate, esters of fatty acids, fatty esters of carboxylic acids, mixtures of 2-ethylsuccinic acid, methylglutaric acid and possibly methyldiesters of adipic acid, such asIRIS (a mixture comprising 70 to 95% by weight of dimethyl 2-methylpentanoate, 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 asRPDE。

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

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.

Preferably, the ester or diester solvent of the composition according to the invention corresponds to the formula R _αOOC-A-COOR_α, wherein R _α represents a linear or branched alkyl group comprising 1 to 6 carbon atoms, and preferably represents a methyl group, and a represents a linear or branched alkylene group comprising 2 to 4 carbon atoms.

According to one embodiment, the ester or diester solvent is a compoundIRIS。

Preferably, the total amount of ester or diester solvents other than the 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.

The alkyl acetate solvent that may be used as a further solvent in the composition according to the invention is different from the first solvent having the general formula (a) as defined above.

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

More preferably, the alkyl group of the alkyl acetate solvent is a straight or branched C ₆-C₁₅ alkyl group, even more preferably a C ₆-C₁₃ alkyl group, and even more preferably a C ₆-C₁₂ alkyl group.

Preference may be given to, inter alia, cyclohexyl or hexyl (n-hexyl), ethylhexyl, in particular 2-ethylhexyl, octyl (n-octyl), isooctyl, decyl (n-decyl), isodecyl, tridecyl, dodecyl and 18 undecyl.

Preferably, the total amount of alkyl acetate solvents other than the solvents 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.

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

Preferably, the total amount of sulfoxide solvents 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.

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.

According to a preferred embodiment of the invention, the composition comprises:

(i) At least one first solvent of the general formula (A), preferably butyl levulinate,

(Ii) At least one second solvent of the general formula (C), preferably 2, 2-dimethyl-4-hydroxymethyl-1, 3-dioxolane,

(Iii) At least one amide ester solvent of the formula (B), preferably methyl 5- (dimethylamino) -2-methyl-5-oxopentanoate, as described above, and

(Iv) Optionally at least one additional solvent selected from the group consisting of levoglucosone, dihydrolevoglucosone, derivatives thereof, and mixtures thereof, preferably dihydrolevoglucosone.

According to another preferred embodiment of the invention, the composition comprises:

(Iii) At least one amide solvent of the formula (D), preferably N, N-dimethyldecanoamide, as described above, and

(Iii) At least one amide ester solvent of the general formula (B) as described above, preferably methyl 5- (dimethylamino) -2-methyl-5-oxopentanoate,

(Iv) At least one amide solvent of the formula (D), preferably N, N-dimethyldecanoamide, as described above, and

(V) Optionally at least one additional solvent selected from the group consisting of levoglucosone, dihydrolevoglucosone, derivatives thereof, and mixtures thereof, preferably dihydrolevoglucosone.

From 20% to 90% by weight, in particular from 25% to 85% by weight, relative to the total weight of the composition, of butyl levulinate as first solvent,

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

-Optionally one or more additional solvents selected from the group consisting of methyl 5- (dimethylamino) -2-methyl-5-oxopentanoate, N-dimethyldecanoamide and mixtures thereof, and

-Optionally dihydro-l-glucosone.

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

The 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.

Agrochemical formulations

The agrochemical formulation according to the invention comprises:

a) At least one of the materials used for agriculture,

B) The composition as described above is used in the manufacture of a composition,

C) Optionally at least one emulsifier, preferably a surfactant, and

D) Optionally water.

"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, for example seeds, for controlling pests and/or regulating plant growth and/or inducing a defensive response of plants and/or enhancing metabolic and physiological processes within plants and soil. Agrochemical formulations are described, for example, in T.Tadros (editions), encyclopedia of Colloid AND INTERFACE SCIENCE [ encyclopedia of colloid and interface science ], springer-Verlag Berlin Heidelberg [ Schpulger Press of Berlin Heidelberg ],2013, pages 3 to 80.

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

As mentioned previously, agriculture uses many agricultural materials. They are also referred to as active plant protection products or active materials or active substances.

As used herein, the term "agricultural material" means an active ingredient particularly for agricultural practices, including cultivation of soil for crop growth. However, the use of agricultural materials is not limited to application to crops. The agricultural material may be applied to any surface, for example for the purpose of cleaning or helping or inhibiting the growth of living organisms. Other non-crop applications include, but are not limited to, application to animals, such as livestock, to turf and ornamental plants, and to railway weeds.

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.

Depending on the water solubility of the agricultural material and its loading in the target formulation, it can be very challenging to identify suitable solvents to obtain a chemically and physically stable formulation.

Thus, for agricultural materials having low or relatively low water solubility, the use of an appropriate solvent to prepare a concentrated liquid formulation is of interest. Such concentrated formulations of agricultural materials are typically diluted prior to agricultural use. Dilution by farmers is usually done by mixing agrochemical formulations with water.

Preferably, the agricultural material is a water insoluble agricultural material at 20 ℃ and atmospheric pressure (i.e., 1.013x 10 ⁵ Pa).

More preferably, the agricultural material is soluble in water at 20 ℃ and atmospheric pressure (i.e. 1.013x 10 ⁵ Pa) to no more than 100g/L, even more preferably no more than 20g/L, especially no more than 5g/L, for example no more than 1g/L and even no more than 0.2g/L.

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

Advantageously, the agrochemical formulation according to the invention may comprise at least one pesticide.

For example, these pesticides may be selected from herbicides, fungicides, insecticides, miticides, algicides, molluscicides, miticides, nematicides, biocides and rodenticides.

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 [ cetirizine handbook of pesticides and agrochemicals ]", 2 nd edition, WILLIAM ANDREW Publishing [ William Andrusen ], 2015.

The agrochemical formulation according to the invention may optionally comprise at least one nutrient.

Nutrients refer to chemical elements and compounds that are desirable or necessary to promote or improve plant growth. Nutrients are generally described as macronutrients or micronutrients.

Suitable nutrients for use in the agrochemical formulation according to the invention may be micronutrient compounds, preferably those that are solid or partially soluble at room temperature (20 ℃).

Micronutrients are typically referred to as trace amounts of metals or trace elements and are generally administered at lower doses. Suitable micronutrients include trace elements selected from zinc, boron, chlorine, copper, iron, molybdenum and manganese.

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

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

The agrochemical formulation according to the invention may further comprise at least one macronutrient.

Macronutrients typically refer to those comprising 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.

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

Nitrate and/or ammonium salts, such as ammonium nitrate, including in combination with urea, for example as urean type materials, ammonium nitrate, ammonium phosphate (especially monoammonium phosphate, diammonium phosphate and ammonium polyphosphate), ammonium sulfate and less commonly calcium nitrate, sodium nitrate, potassium nitrate and ammonium chloride;

For phosphorus as a nutrient, the acidic form of phosphorus, such as phosphoric acid, pyrophosphoric acid or polyphosphoric acid, but more typically in salt form, such as ammonium phosphate (especially monoammonium phosphate, diammonium phosphate and ammonium polyphosphate), potassium phosphate (especially monopotassium phosphate and potassium polyphosphate);

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

The agrochemical formulation according to the invention may optionally comprise at least one biostimulant.

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

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

Non-limiting examples of biostimulants include seaweed extracts (e.g., vesicular algae (ascophyllum nodosum)), humic acid (e.g., potassium humate), fulvic acid, inositol, glycine, and combinations thereof.

The agrochemical formulation according to the invention may optionally comprise at least one plant growth regulator.

Plant growth regulators mean active ingredients for influencing the growth characteristics of plants. Examples of the plant growth regulator which can be used in the present invention include, but are not limited to, 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-naphthyloxy acetic acid sodium salt, 3-chloro-4-hydroxyphenylacetic acid, 3-indoleacetic acid, 4-biphenylacetic acid, 4-chlorophenoxyacetic acid (4-CPA), 4-hydroxyphenylacetic acid, 6-benzylaminopurine, auxin (auxindole), alpha-naphthylacetic acid K-salt, beta-naphthyloxy acetic acid, p-chlorophenoxyacetic acid, dicamba, 2, 4-dichloroprop (2, 4, 5-aldrop) propionic acid (fenoprop), indole-3-acetic acid (IAA), indole-3-acetyl-DL-aspartic acid, indole-3-acetyl-tryptophan-3-acetyl-L-butyric acid, indole-L-3-acetyl-L-butyric acid; a-naphthylacetic acid, indole-3-acetic acid methyl ester, naphthylacetamide, naphthylacetic acid (NAA), phenylacetic acid, picloram, potassium naphthenate, sodium naphthenate, 4-hydroxyphenylethanol, 4-CPPU, 6-Benzylaminopurine (BA), 6- (Y, Y-dimethylallylamino) purine (2 iP), 2-iP-2HC1, adenine hemisulfate, benzyl adenine, kinetin, cytokinin (meta-topolin), N6-benzoyladenine, N-benzyl-9- (2-tetrahydropyranyl) adenine (BP A), N- (2-chloro-4-pyridinyl) -N-phenylurea, gibberellic acid (GA 3), gibberellin A4+A7 (GA N), ethylene and abscisic acid.

Several agricultural materials can be combined in one agrochemical formulation according to the invention.

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.

According to a first embodiment of the invention (concentrate composition), the total content of one or more agricultural materials in the agrochemical formulation ranges from 5% to 90% by weight, more preferably from 5% to 70% by weight, even more preferably from 5% to 60% by weight, and in particular from 10% to 60% by weight, relative to the total weight of the agrochemical formulation.

According to a second embodiment of the 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.

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

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

The agrochemical formulation according to the invention may optionally comprise at least one emulsifier.

Emulsifiers are agents intended to promote emulsification after the formulation is placed in the presence of water, and/or stabilization of the emulsion (over time and/or at temperature), for example by avoiding phase separation.

Preferably, the agrochemical formulation according to the invention further comprises at least one surfactant.

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

More preferably, the surfactant is selected from the group consisting of anionic surfactants, nonionic surfactants, and mixtures thereof.

Even more preferably, the surfactant is selected from the group consisting of anionic surfactants, polyalkoxylated nonionic surfactants, and mixtures thereof.

Emulsifiers and surfactants may be used other than agricultural materials.

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

Alkylsulfonic acids, arylsulfonic acids which are optionally substituted by one or more hydrocarbon radicals and whose acid function is partially or completely salified, like C ₈-C₅₀ alkylsulfonic acids, more particularly C ₈-C₃₀, preferably C ₁₀-C₂₂ alkylsulfonic acids, benzenesulfonic acids, naphthalenesulfonic acids which are substituted by one to three C ₁-C₃₀, preferably C ₄-C₁₆ alkyl and/or C ₂-C₃₀, preferably C ₄-C₁₆ alkenyl groups,

Monoesters or diesters of alkylsulfonic acids in which the linear or branched alkyl moiety is optionally substituted by one or more linear or branched C ₂-C₄ hydroxylated and/or alkoxylated (preferably ethoxylated, propoxylated, ethylpropoxylated) groups,

Phosphate esters, more particularly selected from those comprising at least one linear or branched, saturated, unsaturated or aromatic hydrocarbon group comprising from 8 to 40, preferably from 10 to 30 carbon atoms, optionally substituted by at least one alkoxylated (ethoxylated, propoxylated, ethoxylated) group. Furthermore, they contain at least one mono-or di-esterified phosphate group, so that one or two free or partially or completely salified groups can be present. Preferred phosphoric esters are the type of mono-and diesters of phosphoric acid and alkoxylated (ethoxylated and/or propoxylated) mono-, di-or tri-styrylphenols or alkoxylated (ethoxylated and/or propoxylated) mono-, di-or tri-alkylphenols, optionally substituted by one to four alkyl groups, phosphoric acid and alkoxylated (ethoxylated or ethylpropylated) C ₈-C₃₀, preferably C ₁₀-C₂₂ alcohols, phosphoric acid and non-alkoxylated C ₈-C₂₂, preferably C ₁₀-C₂₂ alcohols,

Sulfuric esters obtained from saturated or aromatic alcohols optionally substituted by one or more alkoxylated (ethoxylated, propoxylated, ethylpropoxylated) groups, and for which the sulfuric ester functions occur in the form of free acids or are partially or completely neutralized. By way of example, mention may be made of the sulfates more particularly obtained from saturated or unsaturated C ₈-C₂₀ alcohols which may contain from 1 to 8 alkoxylated (ethoxylated, propoxylated, ethylpropoxylated) units, the sulfates obtained from polyalkoxylated phenols substituted with from 1 to 3 saturated or unsaturated C ₂-C₃₀ hydroxy carbon groups and in which the number of alkoxylated units is comprised between 2 and 40, the sulfates obtained from polyalkoxylated mono-, di-or tri-styrylphenols in which the number of alkoxylated units varies from 2 to 40.

Anionic surfactants may be in the acid form (they are potentially anionic) or in partially or fully salified form together with a counter ion. The counter ion may be an alkali metal (such as sodium or potassium), an alkaline earth metal (such as calcium), or even an ammonium ion of the formula N (R) ₄ ⁺, wherein the R groups are the same or different and represent a hydrogen atom or a C ₁-C₄ alkyl group optionally substituted by an oxygen atom.

As examples of the nonionic surfactant, there may be mentioned, without any intended limitation thereof:

Polyalkoxylated (ethoxylated, propoxylated, ethylpropoxylated) phenols substituted with at least one C ₄-C₂₀, preferably C ₄-C₁₂ alkyl group or with at least one alkylaryl group having a C ₁-C₆ alkyl group in the alkyl portion. More particularly, the total number of alkoxylation units is comprised between 2 and 100. By way of example, polyalkoxylated mono-, di-or tri- (phenylethyl) phenols or polyalkoxylated nonylphenols may be mentioned. Among ethoxylated and/or propoxylated, sulfated and/or phosphated di-or tri-styrylphenols, mention may be made of ethoxylated di- (phenyl-1-ethyl) phenols having 10 oxyethylene units, ethoxylated di- (phenyl-1-ethyl) phenols having 7 oxyethylene units, sulfated ethoxylated di- (phenyl-1-ethyl) phenols having 7 oxyethylene units, ethoxylated tris- (phenyl-1-ethyl) phenols having 8 oxyethylene units, ethoxylated tris- (phenyl-1-ethyl) phenols having 16 oxyethylene units, sulfated ethoxylated tris- (phenyl-1-ethyl) phenols having 16 oxyethylene units, ethoxylated tris- (phenyl-1-ethyl) phenols having 20 oxyethylene units, and phosphated ethoxylated tris- (phenyl-1-ethyl) phenols having 16 oxyethylene units.

Polyalkoxylated (ethoxylated, propoxylated, ethylpropoxylated) C ₆-C₂₂ fatty acids or alcohols. The number of alkoxylation units is comprised between 1 and 60. The term ethoxylated fatty acids includes both products obtained by ethoxylating fatty acids with ethylene oxide as well as those obtained by esterifying fatty acids with polyethylene glycol.

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

Sorbitan esters, which are optionally polyalkoxylated (ethoxylated, propoxylated, ethylpropoxylated), more particularly cyclized sorbitol esters of C ₁₀-C₂₀ fatty acids, such as lauric acid, stearic acid or oleic acid, and which comprise a total number of alkoxylation units comprised between 2 and 50.

Useful emulsifiers are in particular the following products, all of which are sold by the company sorvin:

- TSP/724-surfactants based on ethylene-propoxylated tristyrylphenol,

-796/P: based on ethylene-propylene oxide alkylated triphenyls vinyl phenol surfactant

-CY 8: tribenzene based on ethoxylation vinyl phenol surfactant

-BSU: tribenzene based on ethoxylation vinyl phenol surfactant

-S/25 surfactants based on ethoxylated tristyrylphenols

-3D33 surfactants based on ethoxylated tristyrylphenol phosphate esters

-RC ethoxylated castor oil-based surfactants

-OR/36 surfactants based on ethoxylated castor oil

-VO 2003-ethoxylated castor oil based surfactants

-OL40: based on ethoxylated sorbitan surfactant of alcohol hexaoleate

-T/20 ethoxylated sorbitan ester-based surfactants.

-TBE724: based on ethylene-propylene oxide alkylated triphenyls vinyl phenol surfactant

-TEB25 mixture of surfactants based on ethoxylated castor oil, calcium dodecylbenzenesulfonate and alkoxylated polymers

-60/B dodecylbenzene sulfonate-based surfactants

-60/BE-dodecylbenzene sulfonate-based surfactant.

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.

Preferably, the total amount of the one or more surfactants 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.

Preferably, the total amount of the one or more anionic surfactants 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.

Preferably, the total amount of the one or more nonionic surfactants, in particular the one or more polyalkoxylated nonionic surfactants, in the agrochemical formulation according to the present 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.

Advantageously, the agrochemical formulation according to the invention may further comprise at least one co-solvent.

According to the present invention, a co-solvent may be used that is different from the first solvent, the second solvent and the additional solvent as previously described.

These other solvents or cosolvents are preferably selected from:

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,

Carbon-or heterocyclic hydrocarbons, any of which is saturated, unsaturated or aromatic, possibly containing halogen atoms, phosphorus atoms, sulfur atoms and/or nitrogen atoms and/or functional groups,

More preferably, the co-solvent is selected from:

alkanes, cycloalkanes and aromatic derivatives, for example paraffins having a branched or straight chain such as "white oils" or decalins, mono-, di-or trialkylbenzenes or naphthalenes, under the trade name 100. 150, 200 Standard and ND grade sold compounds;

Aliphatic, cycloaliphatic or aromatic mono-, di-or triesters, for example alkyl alkanoates such as methyl oleate, benzyl alkanoates, alkyl benzoate, gamma butyrolactone, caprolactone, esters of glycerol and citric acid, alkyl salicylates, phthalates, dibenzoates, acetoacetates, glycol ether acetates, dipropylene glycol diacetate;

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

aliphatic, alicyclic or aromatic ketones, such as, for example, dialkyl ketones, benzyl ketones, fenchyl ketones, acetophenones, cyclohexanone, alkylcyclohexanone;

Aliphatic, cycloaliphatic or aromatic alcohols, such as, for example, diols, 2-ethylhexanol, cyclohexanol, benzyl alcohol, tetrahydrofurfuryl alcohol;

aliphatic, cycloaliphatic or aromatic ethers, such as, for example, glycol, notably ethers of ethylene glycol and propylene glycol and their polymers, diphenyl ether of dipropylene glycol, monomethyl ether or monobutyl ether of tripropylene glycol, alkoxyalkanol, dimethyl isosorbide;

fatty acids, such as, for example, linoleic acid, linolenic acid, oleic acid;

Carbonates such as, for example, propylene carbonate or butylene carbonate, lactate, fumarate, succinate, adipate, maleate;

Amides, such as, for example, alkyl dimethyl amides, dimethyl-decanoamides;

-alkyl urea;

amines, such as, for example, alkanolamines, morpholines, N-alkyl-pyrrolidones;

-tetramethylsulfone;

-dimethylsulfoxide;

Halogenated alkanes or halogenated aromatic solvents, such as, for example, chlorinated alkanes or chlorobenzene.

Crystallization inhibitors may also be present in agrochemical formulations according to the invention. The crystallization inhibitor may be a co-solvent as mentioned above. The crystallization inhibitors may also be non-polyalkoxylated fatty alcohols or fatty acids (for example the products sold by the company Solvi may be mentionedOL 700), alkanolamides, polymers, and the like.

The agrochemical formulation 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 modifiers, suspending agents, antifoam agents and defoamers (in particular silicone antifoam agents and defoamers), antirebound agents, antireaching agents, penetration aids, inert fillers (in particular mineral fillers), binders, diluents, antifreeze agents, stabilizers, dyes, emetics, adhesives (adhesion promoters), absorbents, dispersants, disintegrants, wetting agents, preservatives and/or antimicrobial agents.

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 be present in the agrochemical formulation according to the invention, for example in an amount ranging from 0.1% to 20% by weight, in particular 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, in particular from 0.1% to 5% by weight, relative to the total weight of the composition. Those skilled in the art will be able to select these optional additives as well as their amounts such that they do not impair the properties of the agrochemical composition of the present invention.

Advantageously, the agrochemical formulation according to the invention is in liquid form at 20 ℃ and atmospheric pressure (i.e. 1.013x 10 ⁵ Pa) and may be in the form of a concentrate, diluted concentrate, or sprayable dilution of one or more agricultural materials.

Different types of formulations may be used according to different agricultural materials according to the invention. The formulations that can be used depend on the physical form of the agricultural material (e.g. solid or liquid) and on their physicochemical characteristics in the presence of other compounds such as water or solvents.

For practical reasons (e.g. for ease of handling) it may be preferable to use the formulation in liquid form. Depending on the physicochemical properties of the different agricultural materials considered, the formulation 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).

Preferably, the agrochemical formulation according to the invention is in the form of Emulsifiable Concentrates (EC), concentrated emulsions in water (EW), microemulsions (ME), suspoemulsions (SE), oil Dispersions (OD), dispersible Concentrates (DC), capsule Suspensions (CS), soluble Liquids (SL).

Even more preferably, the agrochemical 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 dispersion concentrate or a dispersible concentrate.

Even better, the agrochemical formulation according to the invention is in the form of an Emulsifiable Concentrate (EC).

In particular, it is noted that compositions comprising a solvent of formula (B) and ethyl lactate instead of the first solvent of formula (a) (outside the present invention) are difficult to formulate in the form of Emulsifiable Concentrates (EC), possibly due to the high miscibility of ethyl lactate in water.

The agrochemical formulation according to the invention is generally a concentrated agrochemical formulation and is intended to be spread on a field to be cultivated or cultivated, most often after dilution with water, in order to obtain a diluted composition. Dilution is typically performed by farm operators directly in the barrels ("tank mix"), for example in the barrels of the devices intended to spread the composition. This does not exclude the possibility of the farm operator adding other plant protection products such as fungicides, herbicides, pesticides, insecticides, fertilizers, adjuvants and the like. Thus, the formulation may be used to prepare a formulation of agricultural materials diluted in water by mixing at least one part by weight of the concentrated formulation with at least 10 parts, preferably less than 10,000 parts, of water. The dilution ratio and amount to be applied to the field generally depends on the agricultural material and the desired dosage for treating the field (which 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 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.

According to this embodiment, the pH ranges preferably from 1 to 11, and more preferably from 2.5 to 9.5.

The pH of the composition may be adjusted to the desired value by means of an alkalizing or acidifying agent. Among the alkalizing agents, one or more alkaline agents, such as ammonia, sodium hydroxide or ethanolamine, may be used. By way of example, among the acidifying agents, mention may be made of mineral or organic acids, such as hydrochloric acid or orthophosphoric acid.

According to a particular embodiment of the invention, the agrochemical formulation may advantageously comprise:

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

B) From 5% to 90% by weight, preferably from 10% to 90% by weight, in particular from 30% to 90% by weight, for example from 30% to 80% by weight, relative to the total weight of the agrochemical formulation, of a solvent composition according to the invention,

C) 0.1 to 40% by weight, preferably 1 to 30% by weight, relative to the total weight of the agrochemical formulation, of at least one of said co-solvents,

D) From 0.05 to 40% by weight, preferably from 0.1 to 35% by weight, more preferably from 0.5 to 30% by weight, in particular from 1 to 25% by weight, for example from 1 to 5% by weight, of at least one surfactant with respect to the total weight of the agrochemical formulation,

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.

Known conventional methods for preparing agrochemical formulations or solvent mixtures can be carried out. This can be achieved by simply mixing the components.

The agrochemical formulations according to the invention can be used to kill or inhibit pests and/or to eliminate unwanted plants and/or to inhibit the growth of unwanted plants.

The agrochemical formulation according to the invention can be diluted and applied in a conventional manner to at least one plant, the area adjacent to the plant, the soil suitable for supporting the growth of the plant, the roots of the plant, the leaves of the plant, and/or the seeds suitable for producing the plant, for example by watering (drenching), drip irrigation, spraying, and/or fogging.

In the above description, all the preferred embodiments concerning the components may be used alone or in combination.

The following examples serve to illustrate the invention.

Examples

In the examples of the present invention, the term solvent system is a composition and either a single solvent or a blend of several solvents may be devised.

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

Determination of the maximum solubility of an active or of a combination of actives in a solvent system

The maximum solubility of the active or combination of actives in the solvent system is characterized by visual observation. At a given concentration, one or more active ingredients are considered to be soluble in the solvent system at that concentration if the mixture is clear (with the naked eye). However, if one or more of the active ingredients settle, it is no longer soluble in the solvent system and maximum solubility is achieved.

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

Test 1 description of maximum solubility-test of individual actives (alone) in solvent System

Each active ingredient or combination is added in a point-to-point manner in a different solvent system. The solution was magnetically stirred until completely dissolved. Additional amounts of active ingredient are then added and this operation is repeated until the last part of the added active ingredient is no longer dissolved, after each addition of active ingredient the solution being carefully stirred.

Test 2 description of the test of the combination of Low temperature study-actives

The mixture is prepared by dissolving the active or combination of actives in different solvent systems at a concentration. Each active was weighed separately and added to the solvent system. The following observations were then made:

Visual observation at 25 ℃ -the appearance of the mixture was recorded and the possible presence of crystals was investigated.

Visual observation at 0 ℃ the mixture was left at 0 ℃ for 7 days and the appearance of the mixture and the possible presence of crystals were recorded (CIPAC MT39 test).

Visual observation at nucleation at 0 ℃ -introducing crystals of each active ingredient into solution, taking 7 days at 0 ℃ to nucleate. The mixture was stirred and left at 0 ℃ for another 7 days for nucleation. Note that aspects of the mixture and the presence of crystals were ultimately identified (CIPAC MT39 test).

If the mixture (the only or active combined solvent system) forms a clear solution (a liquid phase that is homogeneous under the naked eye), the solvent system is considered a good system, whereas if a two-phase system (the presence of particles, sediment, crystals or cloudy solutions) is obtained, it is indicated that the solvent system is a poor system.

Test 3 stability after dilution ("emulsion")

The objective was to evaluate the emulsion stability of an emulsion formed by dispersing an Emulsifiable Concentrate (EC) in water at a specified dilution ratio (e.g., 5% as shown below).

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

The cylinder was turned over 10 times in succession for emulsification and then left to stand in a thermostatic bath at 30 ℃ for several hours.

The stability of the emulsion was then assessed in terms of the amount of free 'oil' and/or 'cream', which separated while leaving the emulsion undisturbed for 24 hours. Observations were made after 30 minutes, 2 hours and 24 hours.

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

Example 1 dissolution of active ingredient(s) (exclusively) in binary solvent systems of the present invention

According to the above protocol, prothioconazole, tebuconazole and azoxystrobin were measured at GFbio ReSolv a 200 (as a comparative solvent system),SL191 (as a comparative solvent system, with a Renewable Carbon Index (RCI) of 0.50) and blend 1 (solvent system according to the invention, with RCI of 0.55).

Blend 1 according to the invention consists of 73% by weight GFbio ReSolv 200,200 (n-butyl levulinate) and 27% by weight relative to the total weight of the blend

SL191 (2, 2-dimethyl-4-hydroxymethyl-1, 3-dioxolane).

The values of maximum solubility (in g/100g solvent) are summarized in the following table:

These data indicate that and SL191 compared to the solvent system of the present invention provides acceptable (for tebuconazole) or even improved (for prothioconazole and azoxystrobin) performance in terms of solubilization properties, while increasing RCI (from 0.50 to 0.55).

EXAMPLE 2 dissolution of the active ingredient (sole) in the binary solvent System of the present invention

The following formulations were prepared according to the following schemes:

formulation A200 mg of prothioconazole were mixed with 800. Mu.L of solvent system. The solution was then magnetically stirred.

As in example 1, blend 1 according to the invention consists of GFbio ReSolv% by weight GFbio ReSolv% 200 and 27% by weight, relative to the total weight of the blendSL 191.

RT room temperature (25 ℃ C.)

Formulation a highlights the ability of the solvent system of the present invention to dissolve prothioconazole.

Furthermore, blend 1 of the present invention advantageously exhibits a high RCI (0.55).

EXAMPLE 3 dissolution of the active ingredient (sole) in the solvent System of the invention further comprising an amide ester solvent

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.

Blend 2 according to the invention consists of 58% by weight GFbio ReSolv 200,200, 11% by weight relative to the total weight of the blendSL191 and 31% by weightPolarclean (which comprises methyl 5- (dimethylamino) -2-methyl-5-oxopentanoate).

These data demonstrate that the solvent systems of the present invention (blend 1 and blend 2) yield improved performance in terms of the solubilization properties of prothioconazole, tebuconazole, and azoxystrobin.

EXAMPLE 4 dissolution of the active ingredient (sole) in the solvent System of the present invention further comprising a cycloalkanone-based solvent

The maximum solubility of difenoconazole, picoxystrobin and azoxystrobin in blend 1 (with RCI of 0.55) and blend 3 (with RCI of 0.66) of example 1 was measured according to the protocol described above.

Blend 3 according to the invention consists of 66% by weight GFbio ReSolv 200,200, 10% by weight relative to the total weight of the blendSL191 and 24% by weight(Dihydro-l-glucosone).

These data indicate that the solvent systems of the present invention (blend 1 and blend 3) produced good performance in terms of solubilization, while further having high RCI (0.55 and 0.66, respectively).

EXAMPLE 5 dissolution of the active ingredient(s) (combination) in the solvent System of the present invention further comprising a cycloalkanone-based solvent

5.1 The following formulations were prepared according to the following schemes:

formulation B11.8% by weight of prothioconazole are first added to the solvent system. Then 9.9wt% picoxystrobin was added to the mixture, which was magnetically stirred.

Formulation C5.0 wt% azoxystrobin was first added to the solvent system. Then 9.0wt% tebuconazole was added to the mixture and finally 18.0wt% prochloraz was added. The solution was then magnetically stirred.

As in example 4, blend 3 according to the invention consisted of 66% by weight GFbio ReSolv 200,200, 10% by weight relative to the total weight of the blendSL191 and 24% by weight(Dihydro-l-glucosone).

Characterization was performed as described above.

RT room temperature (25 ℃ C.)

These 2 formulations highlight the ability of the solvent system of the present invention to dissolve the challenging combination of active ingredients.

These formulations remained stable at 0 ℃ for 2 weeks, even when subjected to additional nucleation steps during the last 7 days.

Furthermore, blend 3 of the present invention advantageously exhibits a high RCI (0.66).

5.2 The following formulations D and E were also prepared according to the following protocol:

Formulation D75 mg azoxystrobin and 125mg prothioconazole were mixed with 800. Mu.L solvent system. Then magnetically stirring the solution;

formulation E100 mg azoxystrobin and 150mg prothioconazole were mixed with 750 μl solvent system. The solution was then magnetically stirred.

Characterization was performed as described above.

RT room temperature (25 ℃ C.)

These formulations highlight the combination of the solvent systems of the present invention that are capable of dissolving the challenging active ingredients.

EXAMPLE 6 dissolution of the active ingredient(s) (combination) in the solvent System of the present invention further comprising an amide ester solvent

Formulations B and C were prepared as described in example 5.

As in example 3, blend 2 according to the invention consisted of 58% by weight GFbio ReSolv 200,200, 11% by weight relative to the total weight of the blendSL191 and 31% by weightPolarclean.

Characterization was performed as described above.

RT room temperature (25 ℃ C.)

EXAMPLE 7 dissolution of the active ingredient (sole) in the binary solvent System of the present invention

The following formulation F was prepared according to the following protocol:

Formulation F200 mg of prothioconazole were mixed with 800. Mu.L of solvent system. The solution was then magnetically stirred.

Blend 4 (outside the present invention) consisted of 75% by weight GFbio ReSolv% 100 (ethyl levulinate, previously designated as NXT SOLV 100 by GF biochemicals) and 25% by weight relative to the total weight of the blendSL 191.

Blend 5 according to the invention consists of 75% by weight GFbio ReSolv 200,200 and 25% by weight relative to the total weight of the blendSL 191.

RT room temperature (25 ℃ C.)

Formulation F highlights that blend 5 (the solvent system of the present invention) was able to dissolve prothioconazole.

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 (C ₃ -C ₆ ) alkyl group; and

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

in,

- _R1 and _R2 are independently linear or branched _C1 - _C12 alkyl, _C4 - _C12 cycloalkyl or aryl,

-R ₃ is H, linear or branched (C ₁ -C ₆ )alkyl, (C ₃ -C ₈ )cycloalkyl, or a -C(O)R ₄ group, wherein R ₄ is linear or branched C ₁ -C ₄ alkyl or C ₅ -C ₆ cycloalkyl.

2 . The composition according to claim 1 , wherein, in formula (A), R represents a linear (C ₄ -C ₆ ) alkyl group; more preferably, the first solvent is butyl levulinate.

3. The 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):

- R ₁ and R ₂ are independently linear or branched (C ₁ -C ₁₂ ) alkyl, and/or

- R ₃ is H or linear or branched (C ₁ -C ₆ ) alkyl;

Preferably, R ₁ and R ₂ are each independently a linear or branched (C ₁ -C ₄ )alkyl group, and R ₃ is H; and more preferably, R ₁ and R ₂ are methyl and R ₃ is H.

5. The 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 from 0.5 to 15; more preferably from 1 to 15; even more preferably from 1 to 10; in particular from 1 to 8; and for example from 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 (C ₁ -C ₆ )alkyl group,

-R ² and R ³ are the same or different and are (C ₁ -C ₆ ) alkyl, R ¹ and R ² or R ³ may together form a ring containing 4 to 6 carbon atoms and optionally substituted with one or more (C ₁ -C ₄ ) alkyl groups and/or one or more functional groups selected from -OH groups, -OR' groups, -COOR' groups and -CONR ⁴ R ⁵ groups, wherein R' is (C ₁ -C ₆ ) alkyl, and R ⁴ and R ⁵ are the same or different, indicating (C ₁ -C ₆ ) alkyl.

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”-CONR ₂ R ₃ (D)

in:

-R" is a linear or branched (C ₃ -C ₁₉ )alkyl group, preferably a linear or branched (C ₇ -C ₁₉ )alkyl group, more preferably a linear alkyl group containing 7, 8 or 9 carbon atoms, and even more preferably a linear (C ₉ )alkyl group, and

- R ₂ and R ₃ may be identical or different and represent a hydrogen atom or a (C ₁ -C ₆ )alkyl group, preferably a (C ₁ -C ₄ )alkyl group, more preferably a (C ₁ -C ₂ )alkyl group, and even better a methyl group,

Provided that if R ² is a hydrogen atom, then R ³ is a (C ₁ -C ₆ )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. 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.