WO2020121347A1 - Concentrated suspension containing fluindapyr and use thereof as fungicide in crop plants - Google Patents

Concentrated suspension containing fluindapyr and use thereof as fungicide in crop plants Download PDF

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Publication number
WO2020121347A1
WO2020121347A1 PCT/IT2018/000163 IT2018000163W WO2020121347A1 WO 2020121347 A1 WO2020121347 A1 WO 2020121347A1 IT 2018000163 W IT2018000163 W IT 2018000163W WO 2020121347 A1 WO2020121347 A1 WO 2020121347A1
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Prior art keywords
aqueous suspension
concentrated aqueous
weight
suspension according
fluindapyr
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PCT/IT2018/000163
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French (fr)
Inventor
Elisa GALIMBERTI
Claudio DACARRO
Paolo Bellandi
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Isagro S.P.A.
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Priority to PCT/IT2018/000163 priority Critical patent/WO2020121347A1/en
Publication of WO2020121347A1 publication Critical patent/WO2020121347A1/en

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    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/561,2-Diazoles; Hydrogenated 1,2-diazoles
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A01N25/04Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/12Powders or granules
    • A01N25/14Powders or granules wettable
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/30Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants

Definitions

  • the present invention relates to a concentrated suspension containing fluindapyr and its use as a fungicide in crop plants.
  • Fluindapyr is a succinate dehydrogenase inhibitor (SDHI) , an enzyme linked to the inner mitochondrial membrane that participates in the cellular respiration process .
  • SDHI succinate dehydrogenase inhibitor
  • 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.
  • fluindapyr belongs to the class of N-indanyl-pyrazolcarboxamides and is represented by the formula (I) , shown below:
  • 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.
  • the formulations 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.
  • SC concentrated aqueous suspensions
  • a concentrated aqueous suspension allows to formulate one or more active ingredients without the use of solvents, such as organic solvents, which can give rise to phytotoxicity phenomena. Moreover, the concentrated aqueous suspensions allow to obtain a formulation with a high content of active ingredient, thus reducing the costs and complexity of the packaging used compared to other types of formulations.
  • aqueous suspension involves various issues. Unlike other types of formulation, the aqueous suspension can have physical instability problems over the time due to phenomena of recrystallization, flocculation, phase separation or an increase in viscosity, which in turn cause homogeneity problems relating to the application of the active ingredients, difficulties in diluting and pouring the product and problems relating to the active substance's penetration, which make the fungicidal treatment less effective. There is therefore a need to identify formulations having good physical characteristics, such as homogeneity of the components, absence of flocculation or recrystallization phenomena, optimal viscosity, with these characteristics remaining stable over time.
  • a first object of the present invention is a concentrated aqueous suspension comprising :
  • Fluindapyr is the ISO name of the molecule of the chemical formula 3-difluoromethyl-N- (7-fluoro-l, 1, 3- trimethyl-4 -indanyl) -1-methyl-4 -pyrazolcarboxamide .
  • the fluindapyr is present in the concentrated suspension in an amount within the range from 2% to 70% by weight, more preferably from 5% to 60% by weight, with respect to the weight of said concentrated suspension.
  • the concentrated aqueous suspension according to the present invention in addition to fluindapyr, can comprise at least one further active agrochemical ingredient, or a mixture of two or more further active agrochemical ingredients other than fluindapyr.
  • 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 of a crop.
  • the active agrochemical ingredients are selected from: fungicides, insecticides, nematocides, herbicides, phytoprotectors and/or growth regulators .
  • Fungicides are the particularly preferred agrochemical compounds.
  • the other active ingredients can be, for example, fungicides belonging to a chemical class selected from:
  • fungicidal compounds belonging to the class of triazoles that can be present in the concentrated suspension are azaconazole, bitertanol, bromuconazole, cyproconazole, diphenoconazole, epoxyconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole , imazalil, ipconazole, ipfentrifluconazole , mefentrifluconazole, metconazole, myclobutanil , penconazole, propiconazole, prochloraz, prothioconazole , simeconazole, tebuconazole, triadimefon, triadimenol, triflumizole , triticonazole .
  • fungicidal compounds belonging to the class of imidazoles that can be present in the concentrated suspension are: imazalil, oxpoconazole , pefurazoate, prochloraz, triflumizole .
  • fungicidal compounds belonging to the class of strobilurins that can be present in the concentrated suspension are azoxystrobin, dimoxystrobin, fluoxastrobine, kresoxim-methyl , methominostrobin, orysastrobine , picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxostrobin, trifloxystrobin .
  • fungicidal compounds belonging to the class of copper salts that can be present in the concentrated suspension are copper hydroxide, tetracopper oxychloride, Bordeaux mixture (copper sulphate neutralized with calcium hydroxide) , copper sulphate, alone or in a mixture thereof.
  • fungicidal compounds belonging to the class of phtalimides that can be used in the concentrated suspension are: folpet, captan, captafol.
  • fungicidal compounds belonging to the class of dithiocarbamates that can be used in the concentrated suspension are: febram, maneb, mancozeb, metiram, propineb, thiram, zinc thiazole, zineb, ziram.
  • fungicidal compounds belonging to the class of chloronitriles that can be used in the concentrated suspension is chlorothalonil .
  • fungicidal compounds belonging to the class of acylalanines that can be used in the concentrated suspension are: benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M.
  • the concentrated suspension contains one or more further active ingredients
  • their overall concentration is preferably in the range from 2% to 30% by weight, more preferably from 5% to 25%, with respect to the weight of said concentrated suspension.
  • a concentrated suspension is prepared by grinding one or more of the active ingredients described above in water, in the desired ratios and in the presence of co-formulants .
  • co-formulants such as at least one surfactant with a wetting function and at least one rheological modifier, provide a formulation that is surprisingly stable over time, with an excellent propensity to dilute in water and with an excellent compatibility with other fungicidal products.
  • the at least one surfactant with a wetting function used in the concentrated suspension is preferably selected from: alkylbenzene sulphonates, olefin sulphonates, aliphatic sulfosuccinates, taurates, alkylphenol ethoxylates, ethoxylated block copolymers, ethopropoxylated block copolymers, ethoxylated fatty alcohols, condensed alkyl polysiloxanes , sorbitan esters and mixtures thereof; preferably from: aliphatic sulfosuccinates , ethoxylated fatty alcohols and mixtures thereof.
  • the surfactant with the wetting function is present in the concentrated suspension in an overall amount within the range from 0.1% to 20% by weight, more preferably from 0.5% to 5% by weight, with respect to the weight of said concentrated suspension.
  • the concentrated suspensions can optionally comprise further surfactants, such as for example surfactants with dispersing function.
  • said dispersing surfactants are selected from: alkylpoliglucosides , tristyrlphenol phosphate ethoxylates (salt form) , ethoxylated tristyrylphenol sulphates, ethoxypropoxylated tristyrylphenol, condensed polyalkyl naphthalene sulfonates, lignosulphonates , block copolymers, polyacrylates. More preferably they are selected from condensed polyalkyl naphthalene sulfonates and lignosulphonates .
  • the dispersing surfactant is present in the concentrated suspension in an overall amount within the range from 1% to 20% by weight, more preferably from 2% to 10% by weight, with respect to the weight of said concentrated suspension.
  • the concentrated suspensions according to the present invention can also comprise further co- formulant additives, in particular they comprise at least one rheological modifier.
  • said rheological modifier is selected from: modified natural silicates, preferably atapulgites, bentonites, montmorillonites , carbonates, clay, xanthan gum, guar gum, agar, more preferably from: xanthan gum, atapulgite and mixtures thereof.
  • the rheological modifier is present in the concentrated suspension in an overall amount comprised between 0.05% and 1.5% by weight, more preferably between 0.1% and 1.1% by weight, with respect to the weight of said concentrated suspension.
  • additional compounds can be added to the aforementioned concentrated suspensions, such as anti-foaming agents, biocides, biostats, anticrystallization agents, antifreezes.
  • additional compounds can also be added to the above concentrated suspensions to improve their biological activity, such as penetrating agents, spreaders and anti-drift agents.
  • the Applicant has discovered that the preparation process also allows to obtain a surprisingly stable concentrated suspension with an excellent propensity to dilute in water.
  • a further object of the present invention is a process for preparing a concentrated suspension comprising the following steps:
  • step a subjecting said aqueous suspension of solid particles to grinding to obtain the solid particles in a finely divided form; c. adding at least one rheological modifier, if not present in step a.
  • the rheological modifier can thus be added, alternatively, during the grinding step of the solid particle suspension containing the fluindapyr or at the end of said grinding.
  • the grinding process allows particles of the active ingredient to be obtained in the desired, finely divided form.
  • the average particle size of the active ingredient, expressed as Dv50, is equal to or less than 4 pm.
  • the average particle size of the active ingredient, expressed as Dv90, is equal to or less than 12 pm.
  • the Dv50 index represents the diameter value below which the particles are 50% by volume.
  • the Dv90 index represents the diameter value below which the particles are 90% by volume.
  • the Dv50 and Dv90 indices can be determined through Dynamic Light Scattering (DLS) measurements.
  • DLS Dynamic Light Scattering
  • the concentrated suspensions according to the present invention exhibit a high level of fungicidal activity and do not show any phytotoxicity towards the crops to which they are applied.
  • a further object of the present invention is the use of the above concentrated suspensions 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 concentrated suspensions described above to a crop plant .
  • crops of interest are: fruit trees, vegetables and extensive crops, such as rice, wheat and soy.
  • the concentrated suspensions according to the present invention can be applied, after dispersion in water, to any part of a 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 concentrated suspension according to the present invention can be used to prepare a suspension diluted in water, by combining said concentrated suspension with water, optionally in the presence of other ingredients, such as wetting agents, emulsifying agents, etc..
  • the additional ingredients can also be present in the water used to prepare the suspension in water.
  • a further object of the present invention is therefore a process for preparing an agronomic formulation in the form of a diluted aqueous suspension comprising :
  • the dilution water is added in the amount necessary to achieve the required diluted aqueous suspension volume.
  • the quantity of concentrated suspension to be applied to a crop plant, eventually after dilution, to obtain the desired agrochemical effect can vary depending on various factors such as, for example, the crop, climatic conditions, soil characteristics, the method of application.
  • Concentrated suspensions (SC) n. 1-4 according to the present invention having the compositions shown in table 1 were prepared.
  • Attagel 40 atapulgite
  • Antifoam 140 dimethylpolysiloxane
  • Lamfix SO carboxymethylcellulose .
  • the concentrated suspensions n. 1-4 were subjected to the accelerated stability test (according to Cipac MT 46.1), which aims at accelerating the ageing of a product through heating. This test allows to simulate the stability of a formulation after two years of storage at room temperature.
  • 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 visually verified that the formulation did not exhibit 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 dispersion subjected to accelerated stability test, after dilution in water.

Abstract

The present invention relates to a concentrated aqueous suspension comprising: a) at least the active agrochemical ingredient fluindapyr suspended in a finely divided form in an aqueous phase; b) at least one wetting surfactant; c) at least one rheological modifier; and its use as a fungicide in crop plants.

Description

"CONCENTRATED SUSPENSION CONTAINING FLUINDAPYR AND USE THEREOF AS FUNGICIDE IN CROP PLANTS"
The present invention relates to a concentrated suspension 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:
Figure imgf000002_0001
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.
Some agropharmaceuticals are validly used in the form of concentrated aqueous suspensions (SC) , a specific type of liquid formulation characterized by the presence of one or more active ingredients in the form of solid particles dispersed homogeneously in water, which is produced to be subsequently diluted with appropriate volumes of water before being applied to the cultivation area.
A concentrated aqueous suspension allows to formulate one or more active ingredients without the use of solvents, such as organic solvents, which can give rise to phytotoxicity phenomena. Moreover, the concentrated aqueous suspensions allow to obtain a formulation with a high content of active ingredient, thus reducing the costs and complexity of the packaging used compared to other types of formulations.
The formulation of a concentrated aqueous suspension, however, involves various issues. Unlike other types of formulation, the aqueous suspension can have physical instability problems over the time due to phenomena of recrystallization, flocculation, phase separation or an increase in viscosity, which in turn cause homogeneity problems relating to the application of the active ingredients, difficulties in diluting and pouring the product and problems relating to the active substance's penetration, which make the fungicidal treatment less effective. There is therefore a need to identify formulations having good physical characteristics, such as homogeneity of the components, absence of flocculation or recrystallization phenomena, optimal viscosity, with these characteristics remaining stable over time.
DESCRIPTION
The Applicant has discovered that the above- mentioned drawbacks of the state of the art, which will be better illustrated in the description that follows, can at least partially be overcome by using a concentrated aqueous suspension containing fluindapyr and certain co-formulants as well as a specific preparation process to formulate the aforesaid concentrated aqueous suspension. The co- formulants and preparation process allow to obtain a concentrated aqueous suspension that is surprisingly stable over time, with an excellent propensity to dilute in water and have excellent compatibility with other fungicidal products .
Consequently, a first object of the present invention is a concentrated aqueous suspension comprising :
a) at least the active agrochemical ingredient fluindapyr suspended in a finely divided form in an aqueous phase;
b) at least one wetting surfactant;
c) at least one rheological modifier.
Fluindapyr is the ISO name of the molecule of the chemical formula 3-difluoromethyl-N- (7-fluoro-l, 1, 3- trimethyl-4 -indanyl) -1-methyl-4 -pyrazolcarboxamide .
Preferably, the fluindapyr is present in the concentrated suspension in an amount within the range from 2% to 70% by weight, more preferably from 5% to 60% by weight, with respect to the weight of said concentrated suspension.
The concentrated aqueous suspension according to the present invention (hereinafter also indicated only with "concentrated suspension"), in addition to fluindapyr, can comprise at least one further active agrochemical ingredient, or a mixture of two or more further active agrochemical ingredients other than fluindapyr.
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 of a crop.
Preferably, the active agrochemical ingredients are selected from: fungicides, insecticides, nematocides, herbicides, phytoprotectors and/or growth regulators . Fungicides are the particularly preferred agrochemical compounds. The other active ingredients can be, for example, fungicides belonging to a chemical class selected from:
- triazoles;
- imidazoles;
- strobilurins ;
- copper salts;
- phthalimides ;
- dithiocarbamates ;
- chloronitriles ;
- acylalanines .
Examples of fungicidal compounds belonging to the class of triazoles that can be present in the concentrated suspension are azaconazole, bitertanol, bromuconazole, cyproconazole, diphenoconazole, epoxyconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole , imazalil, ipconazole, ipfentrifluconazole , mefentrifluconazole, metconazole, myclobutanil , penconazole, propiconazole, prochloraz, prothioconazole , simeconazole, tebuconazole, triadimefon, triadimenol, triflumizole , triticonazole .
Examples of fungicidal compounds belonging to the class of imidazoles that can be present in the concentrated suspension are: imazalil, oxpoconazole , pefurazoate, prochloraz, triflumizole .
Examples of fungicidal compounds belonging to the class of strobilurins that can be present in the concentrated suspension are azoxystrobin, dimoxystrobin, fluoxastrobine, kresoxim-methyl , methominostrobin, orysastrobine , picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxostrobin, trifloxystrobin .
Examples of fungicidal compounds belonging to the class of copper salts that can be present in the concentrated suspension are copper hydroxide, tetracopper oxychloride, Bordeaux mixture (copper sulphate neutralized with calcium hydroxide) , copper sulphate, alone or in a mixture thereof.
Examples of fungicidal compounds belonging to the class of phtalimides that can be used in the concentrated suspension are: folpet, captan, captafol.
Examples of fungicidal compounds belonging to the class of dithiocarbamates that can be used in the concentrated suspension are: febram, maneb, mancozeb, metiram, propineb, thiram, zinc thiazole, zineb, ziram.
An example of fungicidal compounds belonging to the class of chloronitriles that can be used in the concentrated suspension is chlorothalonil .
Examples of fungicidal compounds belonging to the class of acylalanines that can be used in the concentrated suspension are: benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M.
When the concentrated suspension contains one or more further active ingredients, their overall concentration is preferably in the range from 2% to 30% by weight, more preferably from 5% to 25%, with respect to the weight of said concentrated suspension.
Typically, a concentrated suspension is prepared by grinding one or more of the active ingredients described above in water, in the desired ratios and in the presence of co-formulants .
As stated above, the Applicant has now found that specific co-formulants, such as at least one surfactant with a wetting function and at least one rheological modifier, provide a formulation that is surprisingly stable over time, with an excellent propensity to dilute in water and with an excellent compatibility with other fungicidal products.
The at least one surfactant with a wetting function used in the concentrated suspension is preferably selected from: alkylbenzene sulphonates, olefin sulphonates, aliphatic sulfosuccinates, taurates, alkylphenol ethoxylates, ethoxylated block copolymers, ethopropoxylated block copolymers, ethoxylated fatty alcohols, condensed alkyl polysiloxanes , sorbitan esters and mixtures thereof; preferably from: aliphatic sulfosuccinates , ethoxylated fatty alcohols and mixtures thereof.
Preferably, the surfactant with the wetting function is present in the concentrated suspension in an overall amount within the range from 0.1% to 20% by weight, more preferably from 0.5% to 5% by weight, with respect to the weight of said concentrated suspension.
As is well known to a person skilled in the art, the concentrated suspensions can optionally comprise further surfactants, such as for example surfactants with dispersing function.
Preferably, said dispersing surfactants are selected from: alkylpoliglucosides , tristyrlphenol phosphate ethoxylates (salt form) , ethoxylated tristyrylphenol sulphates, ethoxypropoxylated tristyrylphenol, condensed polyalkyl naphthalene sulfonates, lignosulphonates , block copolymers, polyacrylates. More preferably they are selected from condensed polyalkyl naphthalene sulfonates and lignosulphonates .
Preferably, the dispersing surfactant is present in the concentrated suspension in an overall amount within the range from 1% to 20% by weight, more preferably from 2% to 10% by weight, with respect to the weight of said concentrated suspension.
The concentrated suspensions according to the present invention can also comprise further co- formulant additives, in particular they comprise at least one rheological modifier.
Preferably, said rheological modifier is selected from: modified natural silicates, preferably atapulgites, bentonites, montmorillonites , carbonates, clay, xanthan gum, guar gum, agar, more preferably from: xanthan gum, atapulgite and mixtures thereof.
Preferably, the rheological modifier is present in the concentrated suspension in an overall amount comprised between 0.05% and 1.5% by weight, more preferably between 0.1% and 1.1% by weight, with respect to the weight of said concentrated suspension.
Optionally, additional compounds can be added to the aforementioned concentrated suspensions, such as anti-foaming agents, biocides, biostats, anticrystallization agents, antifreezes.
Optionally, additional compounds can also be added to the above concentrated suspensions to improve their biological activity, such as penetrating agents, spreaders and anti-drift agents.
Moreover, as mentioned above, the Applicant has discovered that the preparation process also allows to obtain a surprisingly stable concentrated suspension with an excellent propensity to dilute in water.
Therefore a further object of the present invention is a process for preparing a concentrated suspension comprising the following steps:
a. mixing at least the active agrochemical ingredient fluindapyr, optionally with one or more further active ingredients, with water in the presence of at least one wetting surfactant and optionally at least one rheological modifier to obtain an aqueous suspension of solid particles;
b. subjecting said aqueous suspension of solid particles to grinding to obtain the solid particles in a finely divided form; c. adding at least one rheological modifier, if not present in step a.
The rheological modifier can thus be added, alternatively, during the grinding step of the solid particle suspension containing the fluindapyr or at the end of said grinding.
The grinding process allows particles of the active ingredient to be obtained in the desired, finely divided form.
Preferably, the average particle size of the active ingredient, expressed as Dv50, is equal to or less than 4 pm. Preferably, the average particle size of the active ingredient, expressed as Dv90, is equal to or less than 12 pm.
As is known, the Dv50 index represents the diameter value below which the particles are 50% by volume. The Dv90 index represents the diameter value below which the particles are 90% by volume.
The Dv50 and Dv90 indices can be determined through Dynamic Light Scattering (DLS) measurements.
The concentrated suspensions according to the present invention exhibit a high level of fungicidal activity and do not show any phytotoxicity towards the crops to which they are applied.
Therefore a further object of the present invention is the use of the above concentrated suspensions 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 concentrated suspensions described above to a crop plant .
Examples of crops of interest are: fruit trees, vegetables and extensive crops, such as rice, wheat and soy.
The concentrated suspensions according to the present invention can be applied, after dispersion in water, to any part of a 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 concentrated suspension according to the present invention can be used to prepare a suspension diluted in water, by combining said concentrated suspension with water, optionally in the presence of other ingredients, such as wetting agents, emulsifying agents, etc.. The additional ingredients can also be present in the water used to prepare the suspension in water.
A further object of the present invention is therefore a process for preparing an agronomic formulation in the form of a diluted aqueous suspension comprising :
providing at least one concentrated suspension according to the present invention,
diluting said concentrated suspension with water to obtain said agronomic formulation in the form of a diluted aqueous suspension.
The dilution water is added in the amount necessary to achieve the required diluted aqueous suspension volume. The quantity of concentrated suspension to be applied to a crop plant, eventually after dilution, to obtain the desired agrochemical effect can vary depending on various factors such as, for example, the crop, climatic conditions, soil characteristics, the method of application.
In order to better illustrate the invention, the following examples are now provided, which are to be considered illustrative and non- limiting of the invention.
EXAMPLES
Concentrated suspensions (SC) n. 1-4 according to the present invention having the compositions shown in table 1 were prepared.
The commercial products used for the preparation of the concentrated suspensions are as follows:
Imbirol OT/NA/70, sodium docusate;
Attagel 40, atapulgite;
Antifoam 140, dimethylpolysiloxane ;
- Rhodopol 23, xanthan gum;
Amebact C, 2 , 2 ' , 2 " - (hexahydro-1 , 3 , 5-triazin- 1,3,5-triyl) triethanol;
- Agrocon NS liq. , condensed sodium naphthalene sulfonate;
- Supragil MNS/90, condensed methyl naphthalene sulfonate with formaldehyde;
Agnique PG8105-G, decylglucoside ;
Lamfix SO, carboxymethylcellulose . Table 1
Figure imgf000013_0001
The concentrated suspensions n. 1-4 were subjected to the accelerated stability test (according to Cipac MT 46.1), which aims at accelerating the ageing of a 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 visually verified that the formulation did not exhibit 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 dispersion subjected to accelerated stability test, after dilution in water.
All the samples tested passed the accelerated ageing test, having maintained their state of homogeneous solutions at the end of the heat treatment .

Claims

1. A concentrated aqueous suspension comprising: a) at least the active agrochemical ingredient fluindapyr suspended in a finely divided form in an aqueous phase;
b) at least one wetting surfactant;
c) at least one rheological modifier.
2. The concentrated aqueous suspension according to claim 1, wherein said fluindapyr is present in an amount within the range from 2% to 70% by weight, more preferably from 5% to 60% by weight, with respect to the weight of said concentrated aqueous suspension.
3. The concentrated aqueous suspension according to claim 1, wherein said wetting surfactant is selected from: alkylbenzene sulphonates, olefin sulphonates, aliphatic sulfosuccinates, taurates, alkylphenol ethoxylates, ethoxylated block copolymers, ethopropoxylated block copolymers, ethoxylated fatty alcohols, condensed alkyl polysiloxanes , sorbitan esters and mixtures thereof; preferably from: aliphatic sulfosuccinates, ethoxylated fatty alcohols and mixtures thereof.
4. The concentrated aqueous suspension according to claim 1, wherein said rheological modifier is selected from: modified natural silicates, preferably atapulgites, bentonites, montmorillonites , carbonates, clay, xanthan gum, guar gum, agar; preferably from: xanthan gum, atapulgite and mixtures thereof.
5. The concentrated aqueous suspension according to claim 1, comprising at least one dispersing surfactant, preferably selected from: alkylpoliglucosides , ethoxylated tristyrylphenol phosphates (salt form) , ethoxylated tristyrylphenol sulphates, etho-propoxylated tristyrylphenols, condensed polyalkyl naphthalene sulfonates, lignosulfonates, block copolymers, polyacrylates and mixtures thereof; preferably from: condensed polyalkyl naphthalene sulfonates, lignosulfonates and mixtures thereof .
6. The concentrated aqueous suspension according to claim 1, comprising at least one further active agrochemical ingredient other than fluindapyr selected from: fungicides, insecticides, nematocides, herbicides, phytoprotectors and growth regulators.
7. The concentrated aqueous suspension according to claim 1, comprising at least one further fungicide other than fluindapyr selected from one of the following classes of compounds:
triazoles;
imidazoles;
strobilurins ;
- copper salts;
phthalimides ;
dithiocarbamates ;
chloronitriles ;
acylalanines .
8. The concentrated aqueous suspension according to claim 1, wherein said at least one wetting surfactant is present in an overall amount within the range from 0.1% to 20% by weight, more preferably 0.5% to 5% by weight, with respect to the weight of said concentrated aqueous suspension.
9. The concentrated aqueous suspension according to claim 1, wherein said rheological modifier is present in an overall amount within the range from 0.05% to 1.5% by weight, more preferably 0.1% to 1.1% by weight, with respect to the weight of said concentrated aqueous suspension.
10. The concentrated aqueous suspension according to claim 5, wherein said at least one dispersing surfactant is present in an overall amount within the range from 1% to 20% by weight, more preferably 2% to 10% by weight, with respect to the weight of said concentrated aqueous suspension.
11. A process for preparing a concentrated aqueous suspension according to claim 1 comprising the following steps:
a. mixing at least the active agrochemical ingredient fluindapyr, optionally with one or more further active ingredients, with water in the presence of at least one wetting surfactant and optionally at least one rheological modifier to obtain an aqueous suspension of solid particles;
b. subjecting said aqueous suspension of solid particles to grinding to obtain the solid particles in a finely divided form;
c. adding at least one rheological modifier, if not present in step a.
12. A process for preparing an agronomic formulation in the form of a diluted aqueous suspension comprising :
providing at least one concentrated aqueous suspension according to claim 1,
diluting said concentrated aqueous suspension with water to obtain said agronomic formulation in the form of a diluted aqueous suspension.
13. Use of a concentrated aqueous suspension according to claim 1 as a fungicide in a crop plant.
14. A method for controlling phytopathogenic fungi in a crop plant which comprises applying at least one effective dose of a concentrated aqueous suspension according to claim 1 to a crop plant.
PCT/IT2018/000163 2018-12-14 2018-12-14 Concentrated suspension containing fluindapyr and use thereof as fungicide in crop plants WO2020121347A1 (en)

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