WO2020121344A1

WO2020121344A1 - Emulsifiable concentrate containing fluindapyr and use thereof as fungicide in crop plants

Info

Publication number: WO2020121344A1
Application number: PCT/IT2018/000160
Authority: WO
Inventors: Elisa GALIMBERTI; Claudio DACARRO; Paolo Bellandi
Original assignee: Isagro S.P.A.
Priority date: 2018-12-14
Filing date: 2018-12-14
Publication date: 2020-06-18
Also published as: AR117326A1

Abstract

The present invention relates to an emulsifiable concentrate comprising: - fluindapyr, - at least one solvent N, N-dimethylamide of a fatty acid having from 6 to 16 carbon atoms, - at least one nonionic surfactant; in the absence of 1, 2-cyclohexane dicarboxylic acid diisononyl ester. The present invention also relates to the use of the above emulsifiable concentrate as a fungicide in agricultural crops.

Description

"EMULSIFIABLE CONCENTRATE CONTAINING FLUINDAPYR AND USE THEREOF AS FUNGICIDE IN CROP PLANTS"

The present invention relates to an emulsifiable concentrate containing fluindapyr and its use as a fungicide in crop plants.

BACKGROUND

Fluindapyr is a succinate dehydrogenase inhibitor (SDHI) , an enzyme linked to the inner mitochondrial membrane that participates in the cellular respiration process .

Inhibitors of this enzyme are used as fungicides in the agricultural field and are known for their high level of biological activity and broad spectrum of action.

In particular, fluindapyr belongs to the class of N-indanyl-pyrazolcarboxamides and is represented by the formula (I) , shown below:

Numerous formulations containing succinate dehydrogenase inhibitors are known in the art for use in the agrochemical field. Such formulations can be in the form of solid or liquid preparations, or in the form of solid suspensions in liquids.

In order to be correctly used, the formulations have to be able to solubilize or disperse, or they have to give rise to stable emulsions when diluted in specific volumes of water. The formulations with the addition of water are in turn applied to crops or soils in which a crop is grown, before or after sowing or germination.

Many agropharmaceuticals are validly used in the form of emulsifiable concentrates (EC) , a specific type of liquid agronomic formulation wherein the active ingredient is dissolved in a solvent which is substantially immiscible with water with the addition of surfactants, such as emulsifiers, wetting agents, anti-foaming agents, antifreezes and biological activators, which make it more suitable for use in agriculture. When added to water, the emulsifiable concentrate forms an oil-in-water emulsion.

For example, patent application WO 2018/141575 describes an emulsifiable concentrate consisting of an agropharmaceutical , an amide solvent, a nonionic surfactant and a specific stabilizer, i.e. 1,2- cyclohexane dicarboxylic acid diisononyl ester.

WO 2012/69514 describes emulsifiable concentrates comprising an insoluble pesticide in water, a nonionic surfactant, an acrylate copolymer and at least one organic solvent, which may include among others 1,2- cyclohexane dicarboxylic acid diisononyl ester.

Emulsifiable concentrates have numerous advantages, such as excellent biological activity and high formulation stability in the absence of crystallization phenomena.

However, the use of emulsifiable concentrates involves possible issues relating to phytotoxicity in the crop plants of interest, as well as a high environmental impact due to the presence of organic solvents used for their formulation.

There is therefore a need to limit the quantities of solvent in the emulsifiable concentrates and/or use solvents with a reduced environmental impact.

For the same reasons, it is also desirable to reduce the content of stabilizing agents in emulsifiable concentrates.

DESCRIPTION

The Applicant has found that the aforementioned and other drawbacks of the state of the art, which will be better illustrated in the following description, can be at least partially overcome by using certain N,N- dimethylamides of fatty acids as solvents to formulate an emulsifiable concentrate containing fluindapyr. In addition to effectively dissolving fluindapyr, these solvents allow to obtain emulsifiable concentrates having a low eco-toxicological profile and with which it is possible to prepare oil-in-water emulsions of increased stability, when diluted with water.

Furthermore, the Applicant has surprisingly found that the emulsifiable concentrates containing fluindapyr in combination with the aforementioned N,N- dimethylamide solvents have high stability even in the absence of the 1, 2 -cyclohexane dicarboxylic acid diisononyl stabilizing ester described in the prior art .

Consequently, a first object of the present invention is an emulsifiable concentrate comprising: a) fluindapyr;

b) at least one solvent N, N-dimethylamide of a fatty acid having from 6 to 16 carbon atoms (C₆-C₁₆) , c) at least one nonionic surfactant, in the absence of 1,2-cyclohexane dicarboxylic acid diisononyl ester.

Fluindapyr is the ISO name of the molecule having chemical formula 3-difluoromethyl-N- (7-fluoro-l, 1, 3- trimethyl -4 - indanyl ) - 1 -methyl-4 -pyrazolcarboxamide .

Preferably, the fluindapyr is present in the emulsifiable concentrate in an amount within the range from 0.5% to 40% by weight, more preferably from 5% to 20% by weight, with respect to the weight of said emulsifiable concentrate.

The emulsifiable concentrate according to the present invention, in addition to fluindapyr, may comprise at least one further active agrochemical ingredient, or a mixture of two or more further active agrochemical ingredients other than fluindapyr.

Preferably, the active agrochemical ingredients are selected from: fungicides, insecticides, nematocides, herbicides, phytoprotectors and/or growth regulators. Fungicides are particularly preferred agrochemical compounds .

The additional active ingredients can be, for example, fungicides selected from the following classes of compounds :

- triazoles;

- strobilurins ;

- amidines;

- chloronitriles ;

- picolinamides ;

- salicylamides .

The term "active agrochemical ingredient" or "agrochemical compound" is intended as an active substance which produces a protective effect against harmful organisms, a conservation effect and/or a control effect of a crop; the active agrochemical ingredient is selected, for example, from: fungicides, insecticides, nematocides, herbicides, phytoprotectors and/or growth regulators. Fungicides are particularly preferred agrochemical compounds .

Examples of fungicidal compounds belonging to the class of triazoles that can be present in the emulsifiable concentrate are: azaconazole, bitertanol, bromuconazole , cyproconazole , diphenoconazole , epoxiconazole , fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole , imazalil, ipconazole, ipfentrifluconazole, mefentrifluconazole, metconazole, myclobutanil , penconazole, propiconazole, prothioconazole, simeconazole , tebuconazole, tetraconazole, triadimefon, triadimenol, triflumizole, triticonazole .

In one embodiment, the emulsifiable concentrate contains fluindapyr and prothioconazole as the only further active agrochemical ingredient other than fluindapyr .

In one embodiment, the emulsifiable concentrate contains fluindapyr and at least prothioconazole as a further active agrochemical ingredient other than fluindapyr.

In one embodiment, the emulsifiable concentrate contains fluindapyr and tetraconazole as the only further active agrochemical ingredient other than fluindapyr .

In one embodiment, the emulsifiable concentrate contains fluindapyr and at least tetraconazole as a further active agrochemical ingredient other than fluindapyr .

Examples of fungicidal compounds belonging to the class of strobilurins that can be present in the emulsifiable concentrate are: azoxystrobin, dimoxystrobin, fluoxastrobine , kresoxim-methyl, methominostrobin, orysastrobine, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxostrobin, trifloxystrobin.

Examples of fungicidal compounds belonging to the class of amidines which can be present in the emulsifiable concentrate are: N-ethyl-N-methyl-N ¹ -5 bromo-2-methyl -6- { [3-

(trifluoromethyl) benzyl] thio}pyridyl-3-formamidine, N- ethyl-N-methy1-N ¹ -2 , 5 -dimethyl-6- {hexylthio}pyridyl-3 - formamidine, N-ethyl-N-methyl-N' -2 , 5-dimethyl-6-

{ [cyclohexylmethyl] thio}pyridyl-3-forma idine, N-ethyl- N-methyl-N' -2 , 5 -dimethyl-6- { [2,6- difluorobenzyl] thio}pyridyl-3 -formamidine .

An example of fungicidal compounds belonging to the class of chloronitriles that can be present in the emulsifiable concentrate is chlorothalonil .

Examples of fungicidal compounds belonging to the class of picolinamides which can be present in the emulsifiable concentrate are fenpicoxamid and florylpicoxamid.

An example of fungicidal compounds belonging to the class of salicylamides which can be present in the emulsifiable concentrate is 3-formylamino-2- [ (2-methyl- propanoyl-oxy) methoxy] -N- (3 , 3 , 5 , 5- tetramethylcyclohexyl) benzamide .

When the emulsifiable concentrate contains one or more further active agrochemical ingredients other than fluindapyr, their total concentration (including fluindapyr) is preferably in the range of 3% to 20% by weight, more preferably 4% to 16% by weight, with respect to the weight of said emulsifiable concentrate.

In one embodiment, the emulsifiable concentrate contains prothioconazole in a concentration in the range of 14% to 15% by weight, with respect to the weight of said emulsifiable concentrate.

In one embodiment, the emulsifiable concentrate contains fluindapyr in a concentration in the range of 14% to 15% by weight, and prothioconazole in a concentration of 14% to 15% by weight, preferably 14% by weight, with respect to the weight of said emulsifiable concentrate.

In a further embodiment, the emulsifiable concentrate contains fluindapyr in a concentration in the range of 8% to 9% by weight, and prothioconazole in a concentration from 14% to 15% by weight, with respect to the weight of said emulsifiable concentrate.

In a further embodiment, the emulsifiable concentrate contains tetraconazole in a concentration in the range of 10% to 11% by weight, with respect to the weight of said emulsifiable concentrate.

In a further embodiment, the emulsifiable concentrate contains fluindapyr in a concentration in the range of 10% to 11% by weight, and tetraconazole in a concentration in the range of 10% to 11% by weight, with respect to the weight of said emulsifiable concentrate .

As known in the state of the art, emulsifiable concentrates are prepared by dissolving the active agrochemical ingredient in a mixture of at least one solvent and at least one surfactant.

The Applicant has now found that the N,N- dimethylamide derivatives of fatty acids C₆-Ci₆ are particularly suitable as solvents for the preparation of emulsifiable concentrates containing fluindapyr, as these solvents have a low eco-toxicological profile, as well as provide a very stable and pourable formulation, without crystallization phenomena.

The emulsifiable concentrates according to the invention are also sufficiently stable even in the absence of the stabilizer 1, 2-cyclohexane dicarboxylic acid diisononyl ester which, in some cases, may even reduce its stability.

In another embodiment, the emulsifiable concentrates according to the invention do not contain stabilizers belonging to the dibasic acid ester family.

For the purposes of the present description and annexed claims, the phrases "in the absence of" and "does not contain" with reference to a given compound, in particular with reference to the aforementioned stabilizers, mean that said compound or stabilizer is present in a concentration equal to or lower than 1% by weight with respect to the weight of the emulsifiable concentrate .

Preferably, the hydrocarbon chain of the fatty acid is made up of a number of carbon atoms from 8 to 12 (C₈-C₁₂₎ .

In one embodiment, the fatty acid C₆-C₁₆ is a mono- unsaturated carboxylic acid.

Examples of N, N-dimethylamides of fatty acids C₆- Ci₆ solvents that can be used for the purposes of the present invention are: N, N-dimethyloctanamide, N,N- dimethyldecanamide, N,N-dimethyldodecanamide, N,N- dimethyldecenamide or mixtures thereof .

In a preferred embodiment, the solvent is N,N- dimethyldecanamide .

In the emulsifiable concentrate according to the invention, the above solvent (hereinafter also referred to as "primary solvent") is preferably present in an amount in the range of 10% to 60% by weight, more preferably in the range of 15% to 50% by weight, with respect to the weight of said emulsifiable concentrate.

The primary solvent can also be used in mixtures with at least one second solvent (co-solvent) . Preferably, the co- solvent is selected from: glycerine, monopropylene glycol, alkyl esters Ci-C₄ of fatty acids C₁₂-C₂₂ or water. Preferably, the alkyl ester is a methyl ester.

Examples of alkyl esters C₁-C₄ of fatty acids C₁₂- C22 that can be used as co- solvents for the purposes of the present invention are alkyl esters, in particular methyl esters, of the following fatty acids: oleic acid, linoleic acid, a-linolenic acid, palmitic acid, stearic acid, erucic acid, arachidic acid.

In the emulsifiable concentrate wherein at least one co- solvent is present, the ratio of the total weight of the at least one primary solvent and the total weight of the at least one co-solvent is preferably within the range from 1:4 to 4:1.

In one embodiment, the co-solvent is present in the emulsifiable concentrate in an amount within the range of from 1% to 45% by weight, more preferably within the range of from 5% to 40% by weight, relative to the weight of said emulsifiable concentrate. In a preferred embodiment, no co-solvent is present in the emulsifiable concentrate, but one or more primary solvents are present, more preferably only N, N-dimethyldecanamide .

The at least one nonionic surfactant used in the emulsifiable concentrate has the function of emulsifier (surfactant emulsifier) . In one embodiment, preferably, said nonionic surfactant is selected from: etho- propoxylated block copolymers, acrylic polymers, ethoxylated tristyrylphenols , etho-propoxylated tristyrilphenols , ethoxylated tristyrylphenol phospates (acid form) , ethoxylated tristyrylphenol sulphates (acid form) , alkyl polyglucosides , ethoxylated vegetable oil, ethoxylated sorbitan monolaurate ; ethoxylated fatty alcohols, modified polyether polysiloxanes and mixtures thereof.

Preferably, the nonionic surfactant emulsifier is present in the emulsifiable concentrate in an overall amount within the range from 5% to 40% by weight, more preferably from 7% to 20% by weight, with respect to the weight of said emulsifiable concentrate.

In one embodiment, in addition to the at least one nonionic surfactant, the emulsifiable concentrate can comprise one or more additional surfactants other than nonionic surfactants, such as for example anionic surfactants .

Preferably, said anionic surfactants are selected from: tristyrylphenol phosphate ethoxylates (salt form) , dodecyl benzene sulphonates, sulphosuccinates and mixtures thereof. More preferably said anionic surfactant is an alkaline or alkaline-earth salt of dodecyl benzene sulphonate . The additional surfactants other than nonionic surfactants are present in the emulsifiable concentrate preferably in an overall amount comprised in the range from 1% to 15% by weight, more preferably in the range from 2% to 10% by weight, with respect to the weight of said emulsifiable concentrate.

The emulsifiable concentrates according to the present invention can also comprise further coformulating additives, such as anti-foaming agents.

Optionally, to the above emulsifiable concentrates, further compounds can also be added to improve their biological activity, such as anti-drift agents, penetrating agents, wetting agents and spreaders .

The preparation of the emulsifiable concentrates according to the present invention can be carried out according to known methods, for example by mixing the components in the desired ratios, without particular limitations in the order in which the components are mixed.

For example, in a first step the active ingredient fluindapyr can be dissolved in the primary solvent; in a second step, at least one nonionic surfactant is added to the solution obtained in the first step. According to an alternative process, fluindapyr is added to the mixture of the primary solvent and the nonionic surfactant.

The emulsifiable concentrates according to the present invention exhibit a high level of fungicidal activity and do not show any substantial phytotoxicity towards the crops to which they are applied.

Therefore a further object of the present invention is the use of the above emulsifiable concentrates for the control of phytopathogenic fungi in a crop plant .

A further object of the present invention is a method for controlling phytopathogenic fungi in a crop plant which comprises applying at least one effective dose of one of the above described emulsifiable concentrates to a crop plant .

Examples of crops of interest are: fruit trees, vegetables and extensive crops, such as rice, wheat and soy.

The emulsifiable concentrates according to the present invention can be applied, as such or in diluted form, on any part of the plant, for example on leaves, stems, branches and roots, or on the seeds themselves before sowing, or on the soil where the plant will grow.

The emulsifiable concentrates according to the present invention are preferably applied to a crop plant in diluted form with water to form an oil-in- water emulsion.

The emulsifiable concentrate according to the present invention can be used to prepare an oil- in water emulsion, combining said concentrate with water, optionally in the presence of other ingredients, such as wetting agents, emulsifying agents, etc.. The additional ingredients can also be present, or present only, in the water used to dilute the emulsifiable concentrate .

A further object of the present invention is therefore a process for preparing an agronomic formulation in the form of an oil-in-water emulsion comprising :

- providing at least one emulsifiable concentrate according to the present invention,

diluting said emulsifiable concentrate with water to obtain said agronomic formulation in the form of an oil-in-water emulsion.

Water is added in the amount necessary to achieve the required oil-in-water emulsion volume.

The quantity of emulsifiable concentrate or the relative emulsion to be applied to a crop plant to obtain the desired agrochemical effect may vary depending on various factors such as, for example, the crop, climatic conditions, soil characteristics, the method of application.

Doses of fluindapyr ranging from 0.5 to 2 L per hectare of crop generally provide sufficient fungicidal activity.

In order to better illustrate the invention, the following examples are provided, which are to be considered illustrative and non-limiting of the invention .

EXAMPLES

Emulsifiable concentrates containing fluindapyr The emulsifiable concentrates n. ECl - ECU were prepared according to the present invention, having the compositions shown in Table 1 (concentrates containing fluindapyr as the only active agrochemical ingredient) and in Table 2 (concentrates containing fluindapyr in admixture with other active agrochemical ingredients) .

The commercial products used for the preparation of emulsifiable concentrates are as follows: Rhodiasolv ADMA 810: mixture of N,N- dimethyloctanamide and N, N-dimethyldecanamide ;

- Rhodiasolv ADMA 10: N, N-dimethyldecanamide ;

- Hallcomid 1025: N,N-dimethyl 9-decenamide ; - Agnique AMD 12: N, N-dimethyldodecanamide ;

- Amesolv CME : mixture of methyl esters of fatty acids from rapeseed oil;

- Soprophor CY/8: ethoxylated tristyrylphenol;

Soprophor TSP/724: etho-propoxylated tristyrylphenol;

Antarox PLG/254: etho-propoxylated block copolymer;

- Rhodacal 60/BE: benzene sulphonic acid calcium salt ;

- Soprophor 796/P: etho-propoxylated tristyrylphneol ;

- Agnique AE829: 1 , 2 -cyclohexane dicarboxylic acid diisononyl ester. Table 1

Table 2

The emulsifiable concentrates n. ECl - ECU were subjected to the accelerated stability test (according to Cipac MT 46.1) which aims at accelerating the ageing of the product through heating. This test allows to simulate the stability of a formulation after two years of storage at room temperature.

The following procedure was used: a certain amount of formulation (for example 500 mL) was placed in a hermetically sealed container and left in an oven at 54 °C for 14 days. After this time, the container was removed from the oven and left to return to room temperature. It was therefore verified that the formulation did not show any phase separation or other phenomena of physical instability, such as flocculation, aggregation or crystalline growth. The chemical stability of the active agrochemical ingredient is also verified, as well as the quality of the emulsion subjected to accelerated stability tests, after dilution in water.

All the samples ECl - ECU passed the accelerated ageing test, having maintained their state of homogeneous solutions at the end of the heat treatment . Determination of fungicidal activity against Puccinia recondita on wheat

Leaves of Salgemma-variety wheat plants, grown in pots in a conditioned environment at 20 °C and 70% R.H. (Relative Humidity) , were treated by spraying both sides of the leaves with the emulsifiable concentrate under examination (see the following Table 3) .

After remaining in the conditioned environment for five days, both sides of the plants' leaves were sprayed with an aqueous suspension of conidia of Puccinia recondita (2 mg of inoculum per 1 ml of solution per infection) .

After spraying, the plants were kept in an environment saturated with humidity and a temperature comprised between 18 and 24 °C for the incubation period of the fungus (1 day) .

At the end of this period, the plants were placed in a greenhouse with 70% R.H. and a temperature of 18-24°C for 14 days .

After this period of time, the external symptoms of the pathogen appeared, and it was therefore possible to carry out a visual evaluation of the intensity of the infection.

The fungicidal activity is expressed as a percentage of reduction, compared to untreated plants (control) , of the leaf area affected by the disease (100 = complete efficacy, 0 = no efficacy) .

The emulsifiable concentrate ECl exhibited excellent control of the disease. Furthermore, productivity at the time of collection was also evaluated.

Table 3 shows the results obtained by carrying out the test described with the above emulsifiable concentrate in comparison with a commercial product, PROLINE^® (emulsifiable concentrate containing prothioconazole 27.5% weight/weight and N, -dimethyldecanamide) :

Table 3

As can be noted, the emulsifiable concentrate according to the invention effectively controlled the disease even at low doses, despite the high level of infection. The application of the emulsifiable concentrate also allowed to increase the production of wheat by about a third compared to the commercial product.

Determination of fungicidal activity against Septoria nodorum on wheat

Leaves of Abate variety wheat plants, grown in pots in a conditioned environment at 20 °C and 70% R.H. (Relative Humidity) , were treated by spraying both sides of the leaves with the emulsifiable concentrate under examination (see the following Table 4) .

After remaining in the conditioned environment for seven days, both sides of the plants' leaves were sprayed with an aqueous suspension of spores of Septoria nodorum (1,000,000 spores/cc) .

After spraying, the plants were kept in an environment saturated with humidity and a temperature comprised between 18 and 24 °C for the incubation period of the fungus (2 days) .

At the end of this period, the plants were placed in a greenhouse with 70% R.H. and a temperature of 18-24°C for 10-12 days.

The emulsifiable concentrate EC7 exhibited excellent control of the disease.

Table 4 shows the results obtained by carrying out the test described with the above emulsifiable concentrate in comparison with the commercial product AVIATOR XPRO^® (emulsifiable concentrate containing bixafen 7.45% weight/weight , prothioconazole 14.90% w/w and N,N- dimethyldecanamide) .

Table 4

As can be noted from the table, the emulsifiable concentrate EC7 also demonstrated high efficacy against Septoria nodorum, providing control similar to that of the commercial standard for that disease.

Stability test of emulsifiable concentrates

(comparative)

The emulsifiable concentrates n. EC2 and EC5 were subjected to a further stability test (according to Cipac MT 36) which aimed to evaluate the stability of an emulsion after 24 hours. Some emulsifiable concentrates were also prepared for comparison according to that which is described in the patent application WO2018/141575 (REC1 - REC6 ) , which were subsequently subjected to the same stability test.

The compositions of the prepared and tested emulsifiable concentrates are shown in Tables 5 and 6. Table 5

W02018/141575

Table 6

Nonionic surfactant used in the examples of

WO2018/141575

For the stability test, the emulsifiable concentrates were poured at a concentration of 5% v/v in standard D Cipac water (hardness 342 ppm), as per the test MT 36. The following procedure was used: a 100ml graduated glass cylinder is filled with 95ml of standard Cipac D water, 5ml of EC formulate are added and the cylinder is closed with a glass stopper. The cylinder is inverted 30 times and left undisturbed at 30°C, observing the stability of the emulsion formed, after 30 minutes, 2 hours and 24 hours. The observations regarding the stability of these emulsifiable concentrates after 30 minutes, 2 hours and 24 hours are reported in Tables 7 and 8.

Table 7

Table 8

The term "stable" means that no separation of oil or non-homogeneity is detected in the emulsion.

The term "n.d." stands for not determined.

As can be seen from Tables 7 and 8, the emulsifiable concentrates EC2 and EC5 according to the invention are stable even after 24 hours, whereas the comparative ones are unstable already after 2 hours. The results show that the 1,2-cyclohexane dicarboxylic acid diisononyl ester compound described in WO2018/141575 does not produce any stabilizing effect in the case of emulsifiable concentrates containing fluindapyr. On the contrary, with the other conditions remaining the same, it negatively affects stability (see REC3 , REC6) .

Claims

1. An emulsifiable concentrate comprising:

- fluindapyr,

- at least one C₆-Ci₆ fatty acid N, N-dimethylamide solvent,

- at least one nonionic surfactant

in the absence of 1 , 2 -cyclohexane dicarboxylic acid diisononyl ester.

2. The emulsifiable concentrate according to the previous claim, wherein said at least one C₆-Cis fatty acid N, N-dimethylamide solvent is selected from: N,N- dimethyloctanamide, N,N-dimethyldecanamide, N,N- dimethyldodecanamide, N, N-dimethyldecenamide and mixtures thereof .

3. The emulsifiable concentrate according to claim

1, wherein said at least one C₆-C₁₆ fatty acid N,N- dimethylamide solvent is present in an amount within the range from 10% to 60% by weight, preferably within the range from 15% to 50% by weight, with respect to the weight of said emulsifiable concentrate.

4. The emulsifiable concentrate according to claim 1 comprising at least one co- solvent selected from: glycerine, monopropylene glycol, Ci-C₄ alkyl esters of C₁₂-C₂₂ fatty acids, water or mixtures thereof.

5. The emulsifiable concentrate according to the previous claim, wherein said Ci~C₄ alkyl ester of a Ci₂- C₂₂ fatty acid is a methyl ester of a fatty acid selected from: oleic acid, linoleic acid, a-linolenic acid, palmitic acid, stearic acid, erucic acid, arachidic acid.

6. The emulsifiable concentrate according to claim 4, wherein the weight ratio between said at least one PCT/IT2018/000160

-25-

C₆-Ci₆ fatty acid N, N-dimethylamide solvent and said at least one co- solvent is within the range of from 1:4 to 4:1.

7. The emulsifiable concentrate according to claim

5 1, wherein said fluindapyr is present in an amount within the range from 0.5% to 40% by weight, preferably from 5% to 20% by weight, with respect to the weight of said emulsifiable concentrate.

8. The emulsifiable concentrate according to claim

10 1, comprising at least one further active agrochemical ingredient other than fluindapyr selected from: fungicides, insecticides, nematocides, herbicides, phytoprotectors or growth regulators .

9. The emulsifiable concentrate according to claim

15 1, comprising at least one further fungicide selected from one of the following classes of compounds:

- triazoles ;

- strobilurins ;

- amidines;

20 - chloronitriles ;

- picolinamides ;

- salicylamides .

10. The emulsifiable concentrate according to claim 1, comprising at least one further fungicide

25 other than fluindapyr selected from:

triazoles: azaconazole, bitertanol, bromuconazole, cyproconazole , difenoconazole , epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imazalil,

30 ipconazole, ipfentrifluconazole, mefentrifluconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triflumizole, triticonazole ;

strobilurins : azoxystrobin, dimoxystrobin, fluoxastrobine, kresoxim-methyl, methominostrobin, orysastrobine, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxostrobin, trifloxystrobin.

11. The emulsifiable concentrate according to claim 9 or 10, wherein said at least one further fungicide other than fluindapyr is present in an overall concentration within the range from 0.5% to 40% by weight, preferably from 5% to 20% by weight, with respect to the weight of said emulsifiable concentrate.

12. The emulsifiable concentrate according to claim 1, wherein said at least one nonionic surfactant is selected from: etho-propoxylated block copolymers, acrylic polymers, ethoxylated tristyrylphenols , etho- propoxylated tristyrylphenols , ethoxylated tristyrylphenol phosphates (acid form) , ethoxylated tristyrylphenol sulphates (acid form) , alkyl polyglucosides, ethoxylated vegetable oil, ethoxylated sorbitan monolaurate, ethoxylated fatty alcohols, modified polyether polysiloxanes and mixtures thereof.

13. The emulsifiable concentrate according to claim 1, wherein said at least one nonionic surfactant is present in the emulsifiable concentrate in an amount within the range from 5% to 40% by weight, preferably from 7% to 20% by weight, with respect to the weight of said emulsifiable concentrate.

14. A process for preparing an agronomic formulation in the form of an oil-in-water emulsion comprising:

- providing at least one emulsifiable concentrate according to claim 1,

diluting said emulsifiable concentrate with water to obtain said agronomic formulation in the form of an oil -in-water emulsion.

15. Use of an emulsifiable concentrate according to claim 1 as a fungicide in a crop plant, said concentrate being applied in an undiluted form or in a form diluted with water to form an aqueous emulsion.

16. A method for controlling phytopathogenic fungi in a crop plant comprising applying at least one effective dose of an emulsifiable concentrate according to claim 1 to a crop plant, said concentrate being applied in an undiluted form or in a form diluted with water to form an aqueous emulsion.