RU2850876C2 - Fungicidal combinations, mixtures and compositions and use thereof - Google Patents

Abstract

FIELD: agriculture.

SUBSTANCE: invention relates to agriculture, particularly plant protection agents. Fungicidal combination contains: (i) an effective amount of the compound of formula I

and (ii) an effective amount of fungicide (A) selected from fluindapyr, wherein the weight ratio of the compound of formula I to fungicide (A) ranges from 10:1 to 1:10. Fungicidal combination is used in a synergistic fungicidal composition in combination with a phytologically acceptable carrier.

EFFECT: fungicidal combination, synergistic fungicidal composition and compound of formula (I) are used against phytopathological fungi, diseases caused by phytopathological fungi by applying to a plant, plant locus, seeds, seedlings and/or soil.

26 cl, 4 dwg, 7 tbl, 6 ex

Description

This application claims the benefit of priority claimed in U.S. Provisional Patent Application No. 62/877,180, filed July 22, 2019, the entire contents of which are incorporated herein by reference.

Throughout this application, various publications are cited. The contents of these documents are incorporated herein by reference in their entirety to provide a more complete description of the prior art in the field to which this invention pertains.

Field of technology to which the invention relates

The present invention relates to combinations comprising (i) a certain amount of a compound of formula I and (ii) a certain amount of at least one fungicide (A) selected from the group consisting of fluindapyr, pidiflumetofen, mefentrifluconazole, inprifluxam, isofetamide and a Qi inhibitor. The present invention also relates to compositions comprising the combinations of the present invention and to methods of using the combinations of the present invention.

Prior art

Fungicides are natural or synthetic compounds that protect plants from damage caused by fungi. Modern agricultural practices rely heavily on the use of fungicides. In fact, some crops cannot be grown normally without fungicides. The use of fungicides increases the yield and quality of crops, and therefore increases the value of the harvest. In most cases, the increase in crop value is at least three times greater than the cost of using the fungicide.

5-Fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1H)-one is a compound that provides control of various pathogens that attack economically important agricultural crops, including (but not limited to) the wheat leaf spot pathogen Zymoseptoria tritici (SEPTTR), and fungi from the classes Ascomycetes and Basidiomycetes.

5-Fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1H)-one has both prophylactic and therapeutic effects.

The use of N3-substituted-N1-sulfonyl-5-fluoropyrimidinone derivatives as fungicides is described in U.S. Patent No. 8,263,603, issued September 11, 2012, the contents of which are incorporated herein by reference in their entirety. Methods for preparing 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1H)-one are described in U.S. Patent No. 9,850,215, issued December 26, 2017, and U.S. Patent No. 9,840,476, issued December 12, 2017, the contents of each of which are incorporated herein by reference in their entirety.

U.S. Patent No. 8,263,603 also describes fungicidal compositions for controlling or preventing fungal attack, comprising N3-substituted-N1-sulfonyl-5-fluoropyrimidinone derivatives and a phytologically acceptable carrier, and methods of using the same.

The use of 5-fluoro-4-imino-3-(alkyl/substituted alkyl)-1-(arylsulfonyl)-3,4-dihydropyrimidin-2(1H)-one for seed treatment to prevent or control plant disease is described in U.S. Patent Application No. 2018/0000082, published January 4, 2018.

Synergistic mixtures containing 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1H)-one and at least one fungicidal sterol biosynthesis inhibitor are described in U.S. Patent No. 9,526,245, issued December 27, 2016, and U.S. Patent No. 10,045,533, issued August 14, 2018.

Synergistic mixtures containing 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1H)-one and at least one succinate dehydrogenase inhibitor are described in U.S. Patent No. 9,532,570, issued January 3, 2017, and U.S. Patent No. 10,045,534, issued August 14, 2018.

Many fungicides cannot be used in all situations, and repeated use of a single fungicide often leads to the development of resistance to the corresponding fungicides. Consequently, fungicides and fungicide combinations are being developed that are safer, more effective, last for longer periods, require lower dosages, are easier to apply, and are less expensive.

The present invention provides synergistic combinations, including mixtures, comprising a compound of Formula I and at least one additional fungicide. Another aspect of the present invention is the development of a composition and use of these synergistic combinations, including mixtures.

Brief description of the invention

The present invention describes a fungicidal combination comprising:

(i) a certain amount of a compound of formula I

and (ii) a certain amount of at least one fungicide (A) selected from the group consisting of fluindapyr, pydiflumetofen, mefentrifluconazole, inprifluxam, isofetamide and Qi-inhibitor.

The present invention also describes a mixture containing the combinations of the present invention.

The present invention also describes a composition comprising the combinations of the present invention.

The present invention also provides a method of treating a plant or locus against a fungal infection, comprising applying (i) a certain amount of a compound of formula I

and (ii) a determined amount of at least one fungicide (A) selected from the group consisting of fluindapyr, pydiflumetofen, mefentrifluconazole, inprifluxam, isofetamide and Qi-inhibitor, so as to treat the plant or locus against a fungal infection.

The present invention also describes a method of treating a plant or locus against a fungal infection, comprising applying an effective amount of any of the combinations, mixtures or compositions of the present invention to the plant or locus so as to treat the plant or locus against the fungal infection.

The present invention also describes a method for controlling a plant disease caused by phytopathological fungi, comprising contacting a plant or a locus of a plant with an effective amount of any of the combinations, mixtures or compositions of the present invention, to thereby control the plant disease.

The present invention also describes a method for controlling a fungal attack on a plant, seed or seedling, comprising applying any of the combinations, mixtures or compositions of the present invention to the plant, seed, seedling and/or plant locus, to thereby treat or prevent a fungal attack on the plant, seed or seedling.

The present invention also describes a method for controlling a fungal attack on a plant, seed or seedling, comprising applying any of the combinations, mixtures or compositions of the present invention to a plant, seed, seedling and/or plant locus to thereby control a fungal attack on the plant, seed or seedling.

The present invention also describes a method for treating a plant, seeds or seedlings to obtain a plant resistant to attack by a fungus, wherein said method comprises applying any of the combinations, mixtures or compositions of the present invention to a plant, seeds intended for growing a plant, seedlings intended for growing a plant, or to a locus of a plant, to thereby obtain a plant resistant to attack by a fungus.

The present invention also describes a method for protecting a plant from attack by a fungus, wherein said method comprises applying any of the combinations, mixtures or compositions of the present invention to a plant, a locus of a plant or seeds or seedlings intended for growing a plant to thereby protect the plant from attack by a fungus.

The present invention also describes a plant resistant to attack by a fungus, wherein seeds intended for growing the plant, seedlings intended for growing the plant, or a locus of the plant are treated with any of the combinations, mixtures or compositions of the present invention.

The present invention also describes plant seeds or seedlings adapted to produce a plant resistant to attack by a fungus, wherein the plant seeds or seedlings are treated with any of the combinations, mixtures or compositions of the present invention.

The present invention also describes a method for controlling a fungal attack on a plant, comprising applying any of the combinations, mixtures or compositions of the present invention to a locus, plant, roots, leaves, seeds, fungal locus and/or locus in which infection is to be prevented in order to counteract the fungal attack on the plant.

The present invention also describes a method for controlling fungal diseases of a plant and/or soil, comprising applying any of the combinations, mixtures or compositions of the present invention to the soil, plant, roots, leaves, seeds, fungal locus and/or locus in which infection is to be prevented in order to counteract fungal diseases of the plant and/or soil.

The present invention also describes a method for controlling a plant disease caused by phytopathological fungi, comprising contacting a plant, plant propagation material or plant locus with (i) a certain amount of a compound of formula I

and (ii) a certain amount of at least one fungicide (A) selected from the group consisting of fluindapyr, pydiflumetofen, mefentrifluconazole, inprifluxam, isofetamide and Qi-inhibitor, to thereby control a plant disease.

The present invention also describes a method for controlling a fungal attack on a plant, seed or seedling, comprising applying to the plant, seed, seedling and/or locus of the plant (i) a certain amount of a compound of formula I

and (ii) a determined amount of at least one fungicide (A) selected from the group consisting of fluindapyr, pydiflumetofen, mefentrifluconazole, inprifluxam, isofetamide and a Qi inhibitor, to thereby control the attack of the fungus on the plant, seed or seedling.

The present invention also describes a method for protecting a plant, seed or seedling from attack by a fungus, comprising applying to the plant, seed, seedling and/or locus of the plant (i) a certain amount of a compound of formula I

and (ii) a determined amount of at least one fungicide (A) selected from the group consisting of fluindapyr, pydiflumetofen, mefentrifluconazole, inprifluxam, isofetamide and a Qi inhibitor, to thereby protect the plant, seed or seedling from attack by the fungus.

The present invention also describes the use of any of the combinations, mixtures or compositions of the present invention for treating a plant or locus against a fungal infection.

The present invention also describes the use of any of the combinations, mixtures or compositions of the present invention for treating a plant or locus for a fungal infection.

Brief description of the drawings

Fig. 1. Comparison of the area under the disease curve (AUC) for the intensity of Zymoseptoria tritici line Mg Tri-R6 infection (21 and 28 days after inoculation) on the first leaf of wheat cv. Alixan seedlings for the following groups: control without treatment, group treated with the compound of formula I (5 or 10 g AI/ha), mefentrifluconazole (0.39 g AI/ha), a mixture of mefentrifluconazole (0.39 g AI/ha) and the compound of formula I (5 g AI/ha), or a mixture of mefentrifluconazole (0.39 g AI/ha) and the compound of formula I (10 g AI/ha). Values followed by the same letters are not significantly different according to the Newman-Keuls test (p < 0.05).

Fig. 2. Comparison of the area under the disease curve (AUC) for the intensity of Zymoseptoria tritici line Mg Tri-R6 infection (21 and 28 days after inoculation) on the first leaf of wheat cv. Alixan seedlings for the following groups: control without treatment, group treated with the compound of formula I (5 or 10 g AI/ha), fenpicoxamide (0.39 g AI/ha), a mixture of fenpicoxamide (0.39 g AI/ha) and the compound of formula I (5 g AI/ha), or a mixture of fenpicoxamide (0.39 g AI/ha) and the compound of formula I (10 g AI/ha). Values followed by the same letters are not significantly different according to the Newman-Keuls test (p < 0.05).

Fig. 3. Comparison of the area under the disease curve (AUC) for the intensity of Zymoseptoria tritici Mg Tri-R6 infection (21 and 28 days after inoculation) on the first leaf of Alixan wheat seedlings for the following groups: untreated control, treated with the compound of formula I (5 or 10 g AI/ha), fluindapyr (0.39 g AI/ha), a mixture of fluindapyr (0.39 g AI/ha) and the compound of formula I (5 g AI/ha), or a mixture of fluindapyr (0.39 g AI/ha) and the compound of formula I (10 g AI/ha). Values followed by the same letters are not significantly different according to the Newman-Keuls test (p < 0.05).

Fig. 4. Comparison of the area under the disease curve (AUDC) for the intensity of infection of Zymoseptoria tritici line Mg Tri-R6 (21 and 28 days after inoculation) on the first leaf of wheat seedlings cv. Alixan, for the following groups: control without treatment, group treated with the compound of formula I (5 or 10 g AS/ha), pydiflumetofen (0.0032 g AS/ha, 0.0016 g AS/ha and 0.006 g AS/ha), a mixture of pydiflumetofen (0.00032 g AS/ha) and the compound of formula I (5 g AS/ha), a mixture of pydiflumetofen (0.0016 g AS/ha) and the compound of formula I (5 g AS/ha) or a mixture of pydiflumetofen (0.008 g AS/ha) and the compound of formula I (5 g AS/ha). Values followed by the same letters are not significantly different according to the Newman-Keuls test (p < 0.05).

Detailed description of the invention

Definitions

Unless otherwise defined, all technical and scientific terms used herein have the same meanings as commonly understood by one of ordinary skill in the art to which this invention pertains.

As used herein, the term “compound of formula I” includes all its solid forms, including, but not limited to, amorphous, crystalline, solvate, or hydrated forms. Crystalline forms of the compound of formula I are disclosed in International Patent Application No. PCT No. WO 2019/038583 A1, published February 28, 2019, the entire contents of which are incorporated herein by reference. The term “compound of formula I” also includes its salts and optical isomers.

As used in this text, the term “combination” means a combination of agrochemicals for use together or simultaneously.

In this text, the term "combined," when used in relation to the application of agrochemicals, means that the agrochemicals are applied as a mixture, such as a tank mix. For combined application, the combination may be a ready-mix or individual containers containing the agrochemicals that are mixed before application.

In this text, the term “simultaneously,” when used in relation to the application of agrochemicals, means that an individual agrochemical is applied separately from another agrochemical, or they are mixed simultaneously or at a sufficiently close interval to provide an activity that is additive or greater than additive or synergistic relative to the activity of each agrochemical alone at the same dosage.

As used in this text, the term “mixture” means, but is not limited to, a combination in any physical form, such as a mixture, solution, suspension, dispersion, emulsion, alloy, etc.

As used herein, the term “tank-mix” means that one or more components of a combination, mixture, or composition of the present invention are added and mixed in the tank of a sprayer during or before spraying.

As used herein, the term “composition” includes at least one of the combinations or mixtures of the present invention with an agriculturally acceptable carrier.

As used herein, the term “effective” when used in relation to an amount of an active substance, combination, mixture or composition means an amount of the active substance, combination, mixture or composition that provides an agriculturally significant level of fungal, pathogen and/or disease control when applied to a plant, plant propagation material, soil or locus.

As used in this text, the term "fungicidally effective amount" refers to the amount of active ingredient commercially recommended for use against fungi. The commercially recommended amount for each active ingredient, often indicated as the application rate of the commercial product, can be found on the label accompanying the commercial product. Commercially recommended application rates for commercial products may vary depending on factors such as the plant species and the fungus being controlled.

In this text, the term “effective,” when used in relation to a method of treating a plant or locus against a fungal infection, means that the method provides an agriculturally significant level of treatment without significantly disrupting the normal growth and development of the plant.

As used herein, the term “treating a plant or locus against a fungal infection” includes, but is not limited to, protecting a plant or locus from a fungal infection and/or controlling a fungal infection of a plant or locus.

As used herein, the term “protecting a plant or locus from a fungal infection” includes, but is not limited to, protecting a plant or locus from attack by a fungus, protecting a plant or locus from a fungal disease, and/or preventing a fungal infection of a plant or locus.

As used herein, the term “controlling a fungal infection of a plant or locus” includes, but is not limited to, controlling a fungal disease infecting a plant or locus, controlling a plant or soil disease caused by phytopathological fungi, controlling a fungal attack on a plant or locus, reducing a fungal infection of a plant or locus, and/or treating a plant or locus disease caused by phytopathological fungi.

As used in this text, the term “more effective in protecting a plant or locus from fungal attack” includes, but is not limited to, prolonging the time of protection from fungal attack after treatment and extending the period of protection from fungal attack.

As used in this text, the term “more effective in controlling a fungal disease” includes, but is not limited to, increasing the effectiveness of controlling a fungal disease and decreasing the time required to achieve a given level of fungal control.

As used herein, the term "protective application" refers to the application of one or more fungicides to prevent fungal infection of a plant or locus, where the fungicide combination, mixture, or composition is applied before infection occurs, before any disease symptoms appear, or when disease pressure is low. Disease pressure can be estimated based on conditions associated with disease development, such as spore concentrations and specific environmental conditions.

As used herein, the term “curative application” means the application of one or more fungicides to control a fungal infection of a plant or locus, wherein the fungicidal combination, mixture, or composition is applied after the infection has occurred or after the symptoms of the disease have appeared.

As used herein, the term "agriculturally acceptable carrier" means carriers known and accepted in the art for the preparation of compositions intended for use in agriculture or horticulture.

As used in this text, the term "adjuvant" is used broadly to refer to any substance that is not itself an active ingredient but that enhances or is intended to enhance the effectiveness of the fungicide with which it is applied. Adjuvants include spreaders, penetrants, compatibility enhancers, and runoff retarders.

As used in this text, the term "agriculturally acceptable inert additives" means any substances that are not active ingredients in themselves but are added to the formulation, such as tackifiers, surfactants, synergists, buffers, acidifiers, antioxidants, antifoams and thickeners.

As used in this text, the term "plant" includes the entire plant, plant organ (e.g., leaves, shoots, branches, roots, trunks, twigs, shoots, fruits, etc.), plant cells, and plant propagating material.

As used in this text, the term "plant" includes agricultural crops, including field crops (soybeans, corn, wheat, rice, etc.), vegetables (potatoes, cabbage, etc.), and fruits (peaches, etc.).

As used in this text, the term "propagation material" means all generative parts of the plant such as seeds and spores, seedlings, and vegetative structures such as tubers, bulbs, tubers, underground shoots, root petioles, shoots, stolons and buds.

As used in this text, the term "locus" includes not only areas where fungal infection has already occurred, but also areas where fungal infection may occur, as well as areas under development. Locus includes, but is not limited to, soil and other plant growing media.

When used in this text, the term “ha” means hectare.

As used herein, the term "excipient" means any substance that does not have significant pesticidal activity, such as surfactant(s), solvent(s), or adjuvant(s). One or more excipients may be added to any combination, mixture, or composition of the present invention.

As used herein, the term “stabilizing surfactant” means any surfactant that enhances the physical and/or chemical stability of a compound of Formula I when added to a liquid combination, mixture, or composition containing a compound of Formula I. In some embodiments, the stabilizing surfactant effectively inhibits crystal growth.

The use of the singular in this text encompasses both singular and plural references unless otherwise specifically stated. Therefore, the terms "one" or "at least one" may be used interchangeably in this application.

In this application, the term "comprising" is used in various embodiments; however, one skilled in the art will appreciate that in certain instances, an embodiment may be described using the terms "consisting essentially of" or "consisting of."

The term "about" as used herein includes a range of ±10% of the stated value. Furthermore, the endpoints of all ranges relating to the same component or property include the endpoints, may be combined, and include all intermediate points and ranges.

It should be understood that when a range of a parameter is indicated, all integers within this range and decimal fractions thereof are also encompassed by the present invention, as if the integers and decimal fractions thereof were explicitly indicated in the present text. For example, the range "from 5 g/ha to 120 g/ha" includes values 5.0 g/ha, 5.1 g/ha, 5.2 g/ha, 5.3 g/ha, 5.4 g/ha, etc. up to 120 g/ha.

All publications, patents, and patent applications mentioned in this specification are herein incorporated by reference in their entirety to the same extent as if each individual publication, patent, or patent application were expressly indicated to be incorporated by reference.

The examples described below illustrate the practical implementation of the subject matter of the invention in certain embodiments, but should not be construed as limiting the scope of the present invention. Other embodiments, obvious to those skilled in the art upon consideration of the specification and the described examples, and falling within the spirit and scope of the claims, are also part of the present invention. The specification, including examples, is illustrative only and does not limit the spirit and scope of the present invention.

Aspects and embodiments of the present invention are described below.

Fungicidal combinations, mixtures and compositions

The present invention describes a fungicidal combination comprising: (i) a certain amount of a compound of formula I

and (ii) a certain amount of at least one fungicide (A) selected from the group consisting of fluindapyr, pydiflumetofen, mefentrifluconazole, inprifluxam, isofetamide and Qi-inhibitor.

The present invention describes a synergistic fungicidal combination comprising: (i) a certain amount of a compound of formula I

and (ii) a certain amount of at least one fungicide (A) selected from the group consisting of fluindapyr, pydiflumetofen, mefentrifluconazole, inprifluxam, isofetamide and Qi-inhibitor.

The present invention describes a fungicidal combination comprising: (i) a certain amount of a compound of formula I

and (ii) a certain amount of at least one fungicide (A) selected from the group consisting of fluindapyr, pidiflumetofen, mefentrifluconazole, inprifluxam, isofetamide and a Qi inhibitor,

where the combination is more effective in treating a plant or locus against a fungal infection than when each fungicide is applied separately in the same amount.

The present invention describes a fungicidal combination comprising: (i) a certain amount of a compound of formula I

and (ii) a certain amount of at least one fungicide (A) selected from the group consisting of fluindapyr, pidiflumetofen, mefentrifluconazole, inprifluxam, isofetamide and a Qi inhibitor,

wherein the amount of the compound of formula I and the amount of the fungicide (A) when applied together is more effective in treating the plant or locus against a fungal infection than when each fungicide in the same amount is applied separately.

The present invention describes a fungicidal combination comprising: (i) a certain amount of a compound of formula I

and (ii) a certain amount of at least one fungicide (A) selected from the group consisting of fluindapyr, pidiflumetofen, mefentrifluconazole, inprifluxam, isofetamide and a Qi inhibitor,

wherein the amount of the compound of formula I applied is less than the fungicidally effective amount of the compound of formula I when the compound of formula I is applied alone, and/or

where the applied amount of fungicide (A) is less than the fungicidally effective amount of fungicide (A) when fungicide (A) is applied alone.

In some embodiments, the combination is synergistic.

In some embodiments, the combination is a mixture. In some embodiments, the mixture is a tank mix. In some embodiments, the mixture is synergistic.

The present invention describes a fungicidal mixture comprising: (i) a certain amount of a compound of formula I

and (ii) a certain amount of at least one fungicide (A) selected from the group consisting of fluindapyr, pydiflumetofen, mefentrifluconazole, inprifluxam, isofetamide and Qi-inhibitor.

The present invention describes a synergistic fungicidal mixture comprising: (i) a certain amount of a compound of formula I

and (ii) a certain amount of at least one fungicide (A) selected from the group consisting of fluindapyr, pydiflumetofen, mefentrifluconazole, inprifluxam, isofetamide and Qi-inhibitor.

The present invention describes a fungicidal mixture comprising: (i) a certain amount of a compound of formula I

and (ii) a certain amount of at least one fungicide (A) selected from the group consisting of fluindapyr, pidiflumetofen, mefentrifluconazole, inprifluxam, isofetamide and a Qi inhibitor,

where the mixture is more effective in treating a plant or locus against a fungal infection than when each fungicide is applied separately in the same amount.

The present invention describes a fungicidal mixture comprising: (i) a certain amount of a compound of formula I

and (ii) a certain amount of at least one fungicide (A) selected from the group consisting of fluindapyr, pidiflumetofen, mefentrifluconazole, inprifluxam, isofetamide and a Qi inhibitor,

wherein the amount of the compound of formula I and the amount of the fungicide (A) when applied together is more effective in treating the plant or locus against a fungal infection than when each fungicide in the same amount is applied separately.

The present invention describes a fungicidal mixture comprising: (i) a certain amount of a compound of formula I

and (ii) a certain amount of at least one fungicide (A) selected from the group consisting of fluindapyr, pidiflumetofen, mefentrifluconazole, inprifluxam, isofetamide and a Qi inhibitor,

wherein the amount of the compound of formula I applied is less than the fungicidally effective amount of the compound of formula I when the compound of formula I is applied alone, and/or

where the applied amount of fungicide (A) is less than the fungicidally effective amount of fungicide (A) when fungicide (A) is applied alone.

The present invention also provides a fungicidal composition comprising any of the combinations or mixtures of the present invention.

As used herein, the compound of formula I is 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1H)-one and has the structure:

.

As used in this text, fluindapyr is the common name for 3(difluoromethyl)-N-(7-fluoro-2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-1-methyl-1H-pyrazole-4-carboxamide, which has the following structure:

Fluindapyr is a succinate dehydrogenase inhibitor (SDHI).

As used in this text, pydiflumetofen is the common name for 3(difluoromethyl)-N-methoxy-1-methyl-N-[(2S)-1-(2,4,6-trichlorophenyl)propan-2-yl]-1H-pyrazole-4-carboxamide, which has the following structure:

Pidiflumetofen is a succinate dehydrogenase inhibitor (SDHI) fungicide used on soybeans, cereals, vegetables, corn, peanuts, melons, potatoes, fruit trees, grapes, melons and yams to control powdery mildew (Uncinula necator), septoria leaf spot, cercosporiosis, early blight, scab (Venturia pyrina) and grey mould (Botrytis cinerea).

As used in this text, mefentrifluconazole is the common name for 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, which has the following structure:

Mefentrifluconazole is a sterol biosynthesis inhibitor (demethylation inhibitor) fungicide used in cereals against Septoria tritici.

As used in this text, fenpicoxamide is the common name for (3S,6S,7R,8R)-8-benzyl-3-{3-[(isobutyryloxy)methoxy]-4-methoxypyridine-2-carboxamido}-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl isobutyrate, which has the following structure:

.

Fenpicoxamide is a Qi-inhibitor fungicide used against Zymoseptoria tritici.

As used in this text, inprifluxam is the common name for 3(difluoromethyl)-N-[(R)-2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide, which has the following structure:

.

Inprifluxam is a succinate dehydrogenase inhibitor (SDHI).

As used in this text, isofetamide is the common name for N-[1,1-dimethyl-2-(4-isopropoxy-o-tolyl)-2-oxoethyl]-3-methylthiophene-2-carboxamide, which has the following structure:

Isofetamide is a succinate dehydrogenase inhibitor (SDHI).

In some embodiments, the compound of Formula I encompasses any solid form, including, but not limited to, amorphous, crystalline, solvated, or hydrated. Crystalline forms of the compound of Formula I are described in International Patent Application No. PCT WO/2019/038583, published February 28, 2019, the entire contents of which are incorporated herein by reference.

In some embodiments, the fungicide (A) is fluindapyr.

In some embodiments, the fungicide (A) is pydiflumetofen.

In some embodiments, the fungicide (A) is mefentrifluconazole.

In some embodiments, the fungicide (A) is isofetamide.

In some embodiments, the fungicide (A) is inprifluxam.

In some embodiments, the fungicide (A) is a Qi inhibitor.

In some embodiments, the Qi inhibitor is a cyanoimidazole. In some embodiments, the cyanoimidazole is cyazofamid.

In some embodiments, the Qi inhibitor is sulfamoyl triazole. In some embodiments, the sulfamoyl triazole is amisulbrom.

In some embodiments, the Qi inhibitor is picolinamide. In some embodiments, the picolinamide is fenpicoxamide.

In some embodiments, the weight ratio of the compound of Formula I and the fungicide (A) in a combination, mixture, or composition is from 400:1 to 1:100. In some embodiments, the weight ratio of the compound of Formula I and the fungicide (A) in a combination, mixture, or composition is from 200:1 to 1:100. In some embodiments, the weight ratio of the compound of Formula I and the fungicide (A) in a combination, mixture, or composition is from 50:1 to 1:50. In some embodiments, the weight ratio of the compound of Formula I and the fungicide (A) in a combination, mixture, or composition is from 10:1 to 1:10. In some embodiments, the weight ratio of the compound of Formula I and the fungicide (A) in a combination, mixture, or composition is from 5:1 to 1:5. In some embodiments, the weight ratio of the compound of Formula I and the fungicide (A) in a combination, mixture, or composition is from 2:1 to 1:2. In some embodiments, the weight ratio of the compound of Formula I and the fungicide (A) in a combination, mixture, or composition is from 5:1 to 30:1. In some embodiments, the weight ratio of the compound of Formula I and the fungicide (A) in a combination, mixture, or composition is from 10:1 to 30:1. In some embodiments, the weight ratio of the compound of Formula I and the fungicide (A) in a combination, mixture, or composition is from 25:1 to 12.5:1. In some embodiments, the weight ratio of the compound of Formula I and the fungicide (A) in a combination, mixture, or composition is 25:1. In some embodiments, the weight ratio of the compound of Formula I and the fungicide (A) in a combination, mixture, or composition is 12.5:1. In some embodiments, the weight ratio of the compound of Formula I and the fungicide (A) in a combination, mixture, or composition is 1:1.

In some embodiments, the combination, mixture, or composition is synergistic. In some embodiments, the combination, mixture, or composition has a synergistic effect in treating a plant or locus against a fungal infection. In some embodiments, the combination, mixture, or composition has a synergistic therapeutic effect. In some embodiments, the combination, mixture, or composition has a synergistic protective effect.

In some embodiments of the combinations, mixtures and compositions of the present invention, the weight ratio of the compound of formula I to the fungicide (A) at which the fungicidal action is synergistic against SEPTTR in protective and/or curative use is in the range of from about 200:1 to 1:200.

In some embodiments of the combinations, mixtures and compositions of the present invention, the weight ratio of the compound of formula I to the fungicide (A) at which the fungicidal action is synergistic against SEPTTR in protective and/or curative use is in the range of from about 100:1 to 1:100.

In some embodiments of the combinations, mixtures and compositions of the present invention, the weight ratio of the compound of formula I to the fungicide (A) at which the fungicidal action is synergistic against SEPTTR in protective and/or curative use is in the range of from about 50:1 to 1:50.

In some embodiments of the combinations, mixtures and compositions of the present invention, the weight ratio of the compound of formula I to the fungicide (A) at which the fungicidal action is synergistic against SEPTTR in protective and/or curative use is in the range of from about 10:1 to 1:10.

In some embodiments of the combinations, mixtures and compositions of the present invention, the weight ratio of the compound of formula I to the fungicide (A) at which the fungicidal action is synergistic against SEPTTR in protective and/or curative use is in the range of from about 5:1 to 1:1.

In some embodiments, SEPTTR refers to Zymoseptoria tritici.

In some embodiments, the weight ratio of the compound of Formula I to the fungicide (A) wherein the fungicidal effect is synergistic when applied protectively is in the range of about 400:1 to 1:400. In some embodiments, the weight ratio of the compound of Formula I to the fungicide (A) wherein the fungicidal effect is synergistic when applied protectively is in the range of about 200:1 to 1:200. In some embodiments, the weight ratio of the compound of Formula I to the fungicide (A) wherein the fungicidal effect is synergistic when applied protectively is in the range of about 100:1 to 1:100. In some embodiments, the weight ratio of the compound of Formula I to the fungicide (A) wherein the fungicidal effect is synergistic when applied protectively is in the range of about 50:1 to 1:50. In some embodiments, the weight ratio of the compound of Formula I to the fungicide (A) at which the fungicidal activity is synergistic when applied protectively is in the range of about 10:1 to 1:10. In some embodiments, the weight ratio of the compound of Formula I to the fungicide (A) at which the fungicidal activity is synergistic when applied protectively is in the range of about 5:1 to 1:5. In some embodiments, the weight ratio of the compound of Formula I to the fungicide (A) at which the fungicidal activity is synergistic when applied protectively is in the range of about 2:1 to 1:2. In some embodiments, the weight ratio of the compound of Formula I to the fungicide (A) at which the fungicidal activity is synergistic when applied protectively is about 25:1. In some embodiments, the weight ratio of the compound of Formula I to the fungicide (A) at which the fungicidal activity is synergistic when applied protectively is about 12.5:1. In some embodiments, the weight ratio of the compound of Formula I to the fungicide (A) at which the fungicidal activity is synergistic when applied protectively is about 1:1.

In some embodiments, the weight ratio of the compound of Formula I to the fungicide (A) wherein the fungicidal effect is synergistic when applied therapeutically is in the range of about 400:1 to 1:400. In some embodiments, the weight ratio of the compound of Formula I to the fungicide (A) wherein the fungicidal effect is synergistic when applied therapeutically is in the range of about 200:1 to 1:200. In some embodiments, the weight ratio of the compound of Formula I to the fungicide (A) wherein the fungicidal effect is synergistic when applied therapeutically is in the range of about 100:1 to 1:100. In some embodiments, the weight ratio of the compound of Formula I to the fungicide (A) wherein the fungicidal effect is synergistic when applied therapeutically is in the range of about 50:1 to 1:50. In some embodiments, the weight ratio of the compound of Formula I to the fungicide (A) at which the fungicidal effect is synergistic when applied therapeutically is in the range of about 10:1 to 1:10. In some embodiments, the weight ratio of the compound of Formula I to the fungicide (A) at which the fungicidal effect is synergistic when applied therapeutically is in the range of about 5:1 to 1:5. In some embodiments, the weight ratio of the compound of Formula I to the fungicide (A) at which the fungicidal effect is synergistic when applied therapeutically is in the range of about 2:1 to 1:2. In some embodiments, the weight ratio of the compound of Formula I to the fungicide (A) at which the fungicidal effect is synergistic when applied therapeutically is about 25:1. In some embodiments, the weight ratio of the compound of Formula I to the fungicide (A) at which the fungicidal activity is synergistic when administered therapeutically is about 12.5:1. In some embodiments, the weight ratio of the compound of Formula I to the fungicide (A) at which the fungicidal activity is synergistic when administered therapeutically is about 1:1.

In some embodiments, the combination, mixture, or composition further comprises at least one pesticide(s).

In some embodiments, the combination, mixture, or composition comprises at least one stabilizing surfactant. In some embodiments, the combination, mixture, or composition comprises at least two stabilizing surfactants. In some embodiments, the combination, mixture, or composition comprises two stabilizing surfactants. In some embodiments, the combination, mixture, or composition comprises a stabilizing system.

In some embodiments, one of the stabilizing surfactants is a nonionic stabilizing surfactant. In some embodiments, the nonionic stabilizing surfactant is selected from the group consisting of polymers, alkoxylated diethylethanolamine ether, polyalkylene oxide alcohol ether, and alcohols.

In some embodiments, said polymer is a block polymer or a random polymer. In some embodiments, said polymer is a tri-block polymer. In some embodiments, the tri-block polymer is an ABA block polymer. In some embodiments, said polymer has a low HLB (hydrophilic-lipophilic balance) value, preferably an HLB of 5. In some embodiments, said polymer is Atlox™ 4912 (manufactured and sold by Croda).

In some embodiments, said alkoxylated amine ester is Atlox™ 4915 alkoxylated diethylethanolamine, diethyl ethanolamine mono-trimerate, or Atlox™ 4915 (manufactured and sold by Croda).

In some embodiments, the alkoxylated fatty alcohol is Genapol X080 (manufactured and sold by Clariant), Genapol X 050 (manufactured and sold by Clariant), tridecyl alcohol polyglycol ether, Rhodasurf LA 30 (manufactured and sold by Solvay), Aerosol OT-SE or Aerosol OT-100 (manufactured and sold by Solvay), Rhodacal 70/B (manufactured and sold by Solvay), Arlatone TV (manufactured and sold by Croda), Alkamuls A (manufactured and sold by Solvay), or Alkamuls BR (manufactured and sold by Solvay).

In some embodiments, said alcohol has a short carbon chain of C1-C6. In some embodiments, said alcohol has a long carbon chain of C7-C20.

In some embodiments, the nonionic stabilizing surfactant is a nonionic polyalkylene oxide polyaryl alcohol derivative.

In some embodiments, one of the stabilizing surfactants is an ionic surfactant. In some embodiments, the ionic stabilizing surfactant is an anionic stabilizing surfactant. An anionic stabilizing surfactant is a compound that contains an anionic group, such as a phosphonic salt group or a sulfonic salt group. An example of an ionic surfactant suitable for use is sodium dioctyl sulfosuccinate, which is manufactured and sold by Solvay under the name Aerosol® OT-SE.

In some embodiments, the anionic stabilizing surfactant is an anionic derivative of a polyalkylene oxide polyaryl alcohol.

In some embodiments, the combination, mixture, or composition comprises at least one nonionic stabilizing surfactant and at least one anionic stabilizing surfactant. In some embodiments, the stabilizing system comprises at least one nonionic stabilizing surfactant and at least one anionic stabilizing surfactant.

In some embodiments, a combination, mixture, or composition comprising a nonionic stabilizing surfactant and an anionic stabilizing surfactant is an SC composition. In some embodiments, a combination, mixture, or composition comprising a nonionic stabilizing surfactant and an anionic stabilizing surfactant is an SE composition.

In some embodiments, one of the stabilizing surfactants is a polyalkylene oxide polyaryl alcohol derivative. In some embodiments, the polyalkylene oxide polyaryl alcohol derivative is a nonionic polyalkylene oxide polyaryl alcohol derivative. In some embodiments, the surfactant that is a polyalkylene oxide polyaryl alcohol derivative is an anionic polyalkylene oxide polyaryl alcohol derivative.

In some embodiments, the combination, mixture, or composition comprises at least two stabilizing surfactants. In some embodiments, the two stabilizing surfactants are two polyalkylene oxide polyaryl alcohol derivatives. In some embodiments, the two stabilizing surfactants are a nonionic polyalkylene oxide polyaryl alcohol derivative and an anionic polyalkylene oxide polyaryl alcohol derivative.

In some embodiments, the nonionic polyalkylene oxide polyaryl alcohol derivative is a compound comprising an aryl group substituted with at least two aromatic groups.

In some embodiments, the nonionic polyalkylene oxide polyaryl alcohol derivative has the following structure:

In some embodiments, the nonionic polyalkylene oxide polyaryl alcohol derivative has the following structure:

In some embodiments, the anionic polyalkylene oxide polyaryl alcohol derivative is a compound comprising an aryl group substituted with at least two aromatic groups.

In some embodiments, the anionic group in the anionic polyalkylene oxide derivative of a polyaryl alcohol has an anionic group selected from phosphate (PO ₄ ), phosphonate (PO ₃ ), sulfonate (SO ₃ ), and sulfate (SO ₄ ).

Polyalkylene oxides may include, but are not limited to, polyethylene oxide, polypropylene oxide, polybutylene oxide, and any combination thereof. In some embodiments, the polyalkylene oxide group is polyethylene oxide. In some embodiments, the polyalkylene oxide group is polypropylene oxide.

Polyalkylene oxides may include, but are not limited to, copolymers and homopolymers. Copolymers may include, but are not limited to, random polymers and block polymers. In some embodiments, the polyalkylene oxide group is a diblock copolymer. In some embodiments, the polyalkylene oxide group is a triblock copolymer.

In some embodiments, the polyalkylene oxide polyaryl ether is polyalkylene oxide styrylphenyl ether. In some embodiments, the polyalkylene oxide polyaryl ether is polyalkylene oxide benzylphenyl ether. In some embodiments, the polyalkylene oxide polyaryl ether is polyalkylene oxide bisphenyl ether. In some embodiments, the polyalkylene oxide polyaryl ether is polyalkylene oxide tristyrylphenyl ether. In some embodiments, the polyalkylene oxide polyaryl ether is polyalkylene oxide distyrylphenyl ether. In some embodiments, the polyalkylene oxide distyrylphenyl ether is polyoxyethylene distyrylphenyl ether.

In some embodiments, the polyalkylene oxide polyaryl ether is an anionic surfactant. An anionic surfactant is a compound that has an anionic group, such as a phosphonic salt group or a sulfonic salt group.

In some embodiments, said salt comprises a cation. In some embodiments, this cation is selected from the group consisting of sodium, potassium, ammonium, calcium, magnesium, and combinations thereof.

In some embodiments, the anionic polyalkylene oxide polyaryl alcohol derivative has the following structure:

In some embodiments, the anionic polyalkylene oxide polyaryl alcohol derivative is tristyrylphenol ethoxylate phosphate ester.

In some embodiments, the polyalkylene oxide polyaryl ether is a tristyrylphenol ethoxylate phosphate ester. Preferably, the tristyrylphenol ethoxylate phosphate ester is Soprophor® 3D33, which is manufactured and sold by Solvay.

In some embodiments, the polyalkylene oxide polyaryl ether is 2,4,6-tri-(1-phenylethyl)-phenol polyglycol ether with 54 EO. Preferably, the 2,4,6-tri-(1-phenylethyl)-phenol polyglycol ether with 54 EO is Emulsogen® TS 540, which is manufactured and sold by Clariant.

In some embodiments, the polyalkylene oxide polyaryl ether is an ethoxylated tristyrylphenol. Preferably, the ethoxylated tristyrylphenol is Soprophor® TS/54, which is manufactured and sold by Solvay.

In some embodiments, the salt comprises a cation selected from the group consisting of sodium, potassium, ammonium, calcium, magnesium, and combinations thereof.

Polyalkylene oxide polyaryl ether surfactants may include, but are not limited to, polyphenylethylphenol and tristyrylphenol.

Polyalkylene oxide polyaryl ether surfactants may include, but are not limited to, uncapped surfactants, capped surfactants, or a combination thereof.

In some embodiments, the combination, mixture, or composition comprises two or more stabilizing surfactants, and the two stabilizing surfactants are a nonionic surfactant that is a polyalkylene oxide polyaryl ether and an anionic surfactant that is a polyalkylene oxide polyaryl ether. In some embodiments, the nonionic surfactant is tristyrylphenol ethoxylate. In some embodiments, the anionic surfactant is tristyrylphenol ethoxylate phosphate ester.

In some embodiments, the combination, mixture, or composition comprises tristyrylphenol ethoxylate and tristyrylphenol ethoxylate phosphate ester.

In some embodiments, the nonionic polyalkylene oxide polyaryl ether is a compound comprising an ether group substituted with at least two groups containing aromatic rings.

In some embodiments, the polyalkylene oxide group is polyoxyethylene. In some embodiments, the polyalkylene oxide group is polyoxypropylene. In some embodiments, the polyalkylene oxide group is a polyoxyethylene block copolymer. In some embodiments, the polyalkylene oxide group is a polyoxypropylene block copolymer.

Polyalkylene oxides may include, but are not limited to, a polyethoxylated group, a polypropoxylated group, a polybutoxylated group, and any combination thereof.

Polyalkylene oxides may include, but are not limited to, copolymers and homopolymers.

Copolymers may include, but are not limited to, random polymer and block polymer.

In some embodiments, the polyalkylene oxide polyaryl ether is polyalkylene oxide tristyrylphenyl ether. In some embodiments, the polyalkylene oxide tristyrylphenyl ether is polyoxyethylene tristyrylphenyl ether. In some embodiments, the polyalkylene oxide tristyrylphenyl ether is polyoxyethylene polyoxypropylene tristyrylphenyl ether.

In some embodiments, the polyalkylene oxide polyaryl ether is polyalkylene oxide distyrylphenyl ether. In some embodiments, the polyalkylene oxide distyrylphenyl ether is polyoxyethylene distyrylphenyl ether.

In some embodiments, the nonionic polyalkylene oxide polyaryl ether derivative is a tristyrylphenol ethoxylate phosphate ester.

In some embodiments, the stabilizing surfactant is a tristyryl phenol polyethylene glycol ether derivative.

In some embodiments, the stabilizing surfactant is an anionic derivative of tristyryl phenol polyethylene glycol ether.

In some embodiments, the stabilizing surfactant is a nonionic derivative of tristyryl phenol polyethylene glycol ether.

In some embodiments, the combination, mixture, or composition comprises two stabilizing surfactants, and the two stabilizing surfactants are Soprophor 3D33 and Soprophor TS/54 (TSP 54).

In some embodiments, the combination, mixture, or composition comprises two stabilizing surfactants, and both of these stabilizing surfactants are derivatives of polyalkylene oxide polyaryl alcohol. In some embodiments, the combination, mixture, or composition comprises two stabilizing surfactants, wherein one stabilizing surfactant is a nonionic derivative of polyalkylene oxide polyaryl alcohol, and one stabilizing surfactant is an anionic derivative of polyalkylene oxide polyaryl alcohol.

In some embodiments, the combination, mixture, or composition comprises at least two stabilizing surfactants, wherein at least one stabilizing surfactant is a non-ionic polyalkylene oxide polyaryl alcohol derivative, and at least one stabilizing surfactant is an anionic polyalkylene oxide polyaryl alcohol derivative.

In some embodiments, the combination, mixture, or composition comprises two stabilizing surfactants, wherein one stabilizing surfactant is a nonionic polyalkylene oxide polyaryl alcohol derivative, and one stabilizing surfactant is an anionic polyalkylene oxide polyaryl alcohol derivative.

In some embodiments, the stabilizing surfactant is Soprophor 3D33.

In some embodiments, the stabilizing surfactant is tristyrylphenol ethoxylate phosphate ester.

In some embodiments, the polyalkylene oxide polyaryl ether is Soprophor 3D 33 from Solvay.

In some embodiments, the polyalkylene oxide polyaryl ether is Emulsogen TS 540 from Clariant.

In some embodiments, the polyalkylene oxide polyaryl ether is SOPROPHOR TS/54 from Solvay.

In some embodiments, the cation contained in the salt is selected from the group consisting of sodium, potassium, ammonium, calcium, magnesium, and combinations thereof.

Polyaryl may include (but is not limited to) polyphenylethylphenol and tristyrylphenol.

The surfactant which is a polyalkylene oxide polyaryl ether is an unblocked surfactant, a blocked surfactant or a combination of both.

In some embodiments, the surfactant combination comprises a mixture of a nonionic surfactant that is a polyalkylene oxide polyaryl ether and an anionic surfactant that is a polyalkylene oxide polyaryl ether. In some embodiments, the nonionic surfactant is tristyrylphenol ethoxylate. In some embodiments, the anionic surfactant is tristyrylphenol ethoxylate phosphate ester.

In some embodiments, the surfactant combination comprises tristyrylphenol ethoxylate and tristyrylphenol ethoxylate phosphate ester.

In some embodiments, the nonionic polyalkylene oxide polyaryl ether is a compound comprising an ether group substituted with at least two groups containing aromatic rings.

In some embodiments, the polyalkylene oxide group is polyoxyethylene. In some embodiments, the polyalkylene oxide group is polyoxypropylene. In some embodiments, the polyalkylene oxide group is a polyoxyethylene block copolymer. In some embodiments, the polyalkylene oxide group is a polyoxypropylene block copolymer.

Polyalkylene oxides may include, but are not limited to, a polyethoxylated group, a polypropoxylated group, a polybutoxylated group, and any combination thereof.

Polyalkylene oxides may include, but are not limited to, copolymers and homopolymers.

Copolymers may include, but are not limited to, random polymer and block polymer.

In some embodiments, the polyalkylene oxide polyaryl ether is polyalkylene oxide tristyrylphenyl ether. In some embodiments, the polyalkylene oxide tristyrylphenyl ether is polyoxyethylene tristyrylphenyl ether. In some embodiments, the polyalkylene oxide tristyrylphenyl ether is polyoxyethylene polyoxypropylene tristyrylphenyl ether.

In some embodiments, the polyalkylene oxide polyaryl ether is polyalkylene oxide distyrylphenyl ether. In some embodiments, the polyalkylene oxide distyrylphenyl ether is polyoxyethylene distyrylphenyl ether.

In some embodiments, the nonionic polyalkylene oxide polyaryl ether derivative is tristyrylphenol ethoxylate phosphate ester.

In some embodiments, the stabilizing surfactant is Emulsogen TS 540.

In some embodiments, the nonionic surfactant is Emulsogen TS 540

In some embodiments, the stabilizing surfactant is Soprophor TS/54.

In some embodiments, the nonionic polyalkylene oxide polyaryl ether derivative is Soprophor TS/54

In some embodiments, the stabilizing surfactant is an anionic derivative of tristyryl phenol polyethylene glycol ether.

In some embodiments, the stabilizing surfactant is a nonionic derivative of tristyryl phenol polyethylene glycol ether.

In some embodiments, the combination, mixture, or composition comprises a stabilizing system.

In some embodiments, the weight ratio of the compound of Formula I to the nonionic polyalkylene oxide polyaryl alcohol derivative is from 25:1 to 10:1. In some embodiments, the weight ratio of the compound of Formula I to the anionic polyalkylene oxide polyaryl alcohol derivative is from 25:1 to 10:1.

In some embodiments, the combination, mixture, or composition further comprises a phytologically acceptable adjuvant.

In some embodiments, the phytologically acceptable adjuvant is selected from the group consisting of the following:

(i) polyalkylene oxide alkyl ether;

(ii) siloxane-polyalkylene oxide copolymer;

(iii) fatty acid esters;

(iv) vinylpyrrolidones and their derivatives; and

(v) sugar surfactants.

In some embodiments, the polyalkylene oxide alkyl ether is a polyalkoxylated alcohol.

In some embodiments, the alkyl in the polyalkylene oxide alkyl ether includes, but is not limited to, a carbohydrate chain containing C1-C26.

In some embodiments, the alcohol in the polyalkoxylated alcohol includes, but is not limited to, a carbohydrate chain containing C1-C26.

In some embodiments, the alkyl in the polyalkylene oxide alkyl ether includes, but is not limited to, a short carbohydrate chain and a long carbohydrate chain.

Carbohydrate chains can be (but are not limited to) saturated, unsaturated, branched, and unbranched chains.

In some embodiments, the short chain is C1-C8. In some embodiments, the long chain is C9-C26.

In some embodiments, the polyalkylene oxide is, but is not limited to, polyethylene oxide, polypropylene oxide, polybutylene oxide, or combinations thereof.

In some embodiments, the polyalkylene oxide includes, but is not limited to, copolymers. The copolymers are block copolymers, such as polyethylene oxide-polypropylene oxide, and/or random copolymers, such as ethylene oxide-propylene oxide. In some embodiments, the polyalkylene oxide block copolymer is a di-block copolymer. In some embodiments, the polyalkylene oxide block copolymer is a tri-block copolymer.

In some embodiments, the tri-block copolymer is polyethylene oxide/polypropylene oxide/polyethylene oxide.

In some embodiments, the polyalkylene oxide alkyl ether is capped with a terminal alkyl. In some embodiments, this alkyl includes, but is not limited to, a short carbohydrate chain and a long carbohydrate chain. The carbohydrate chains can be, but are not limited to, saturated, unsaturated, branched, and unbranched. In some embodiments, the short chain is C1-C8.

In some embodiments, the polyalkylene oxide alkyl ether is isotridecyl alcohol polyglycol ether.

In some embodiments, the polyalkylene oxide alkyl ether is a C16-C18 alcohol ethoxylate propoxylate ether.

In some embodiments, the C16-C18 alcohol ethoxylate propoxylate ester is Ethylan 995, which is manufactured and sold by Akzo Nobel Agrochemicals. In some embodiments, the C16-C18 alcohol ethoxylate propoxylate ester is Agnique® BP420, which is manufactured and sold by BASF.

In some embodiments, the polyalkylene oxide alkyl ether is an ethoxylate propoxylate alcohol.

In some embodiments, the alcohol ethoxylate propoxylate is Synperonic 13/9, which is manufactured and sold by Croda. In some embodiments, the alcohol ethoxylate propoxylate is Atplus PFA, which is manufactured and sold by Croda.

In some embodiments, the polyalkylene oxide alkyl ether is isotridecyl alcohol polyglycol ether.

In some embodiments, the isotridecyl alcohol polyglycol ether is Genapol X80, which is manufactured and sold by Clariant. In some embodiments, the isotridecyl alcohol polyglycol ether is Trycol®, which is manufactured and sold by BASF.

In some embodiments, the polyalkylene oxide alkyl ether effectively reduces the surface tension of the composition and improves the spreading of the compound of Formula I on the plant leaf. Reducing the surface tension results in reduced leaf runoff.

In some embodiments, the siloxane-polyalkylene oxide copolymer is an organo-modified trisiloxane.

In some embodiments, the siloxane-polyalkylene oxide copolymer is Break Thru S233 from Evonik. In some embodiments, the siloxane-polyalkylene oxide copolymer is Silwett 077 from Momentive.

In some embodiments, a siloxane-polyalkylene oxide copolymer effectively reduces the surface tension of a combination, mixture, or composition. It has been found that a silicone surfactant is an active agent that reduces surface tension and ensures rapid spreading of the combination, mixture, or composition over lipophilic substrates.

In some embodiments, the fatty acid ester may include, but is not limited to, an alkyl ester of a fatty acid and a vegetable oil.

In some embodiments, the alkyl ester comprises a C10-C20 carbohydrate chain.

In some embodiments, the alkyl includes, but is not limited to, a short carbohydrate chain.

Carbohydrate chains can be (but are not limited to) saturated, unsaturated, branched, and unbranched chains.

In some embodiments, the short chain is C1-C8. In some embodiments, the fatty acid alkyl ester is Rhodaphac PA/23 from Solvay (ethoxylated fatty alcohol phosphate ester) or Alkamuls VO/2003 (ethoxylated (18EO) fatty acid) from Solvay.

In some embodiments, the adjuvant is ethoxylated tridecyl alcohol or polyoxyethylene (9) isotridecanol.

In some embodiments, the vegetable oil includes, but is not limited to, vegetable fat and derivatives thereof.

In some embodiments, the vegetable fat includes, but is not limited to, seed oil, coconut oil, canola oil, castor oil, soybean oil, palm oil, and corn oil.

In some embodiments, the vegetable fat derivative is an alkyl ether, polyalkylene oxide.

Polyalkylene oxide means polyethylene oxide, polypropylene oxide, polybutylene oxide and a combination thereof.

In some embodiments, the vegetable fat and its derivatives include, but are not limited to, methylated rapeseed oil ester and polyglycerol fatty acid ester of coconut oil.

In some embodiments, the adjuvant is a mixture of methylated seed oil and a polyglycerol ester.

In some embodiments, the rapeseed oil methyl ester is Agnique ME 18 RDF, which is manufactured and sold by BASF.

In some embodiments, the polyalkylene oxide derivative of vegetable fat is a polyglycerol ester of coconut oil fatty acids.

In some embodiments, the polyglycerol ester of coconut oil fatty acids is Synergen GL5, which is manufactured and sold by Clariant.

In some embodiments, the fatty acid ester softens the surface properties of the sheet to allow improved or more efficient penetration of the compound of Formula I.

In some embodiments, the vinylpyrrolidone derivative is a block copolymer of vinylpyrrolidone and vinyl acetate (VP/VA).

In some embodiments, the block copolymer of vinylpyrrolidone and vinyl acetate is Sokalan VA 64 P, which is manufactured and sold by Ashland.

In some embodiments, the block copolymer of vinylpyrrolidone and vinyl acetate is Agrimer VA 6, which is manufactured and sold by Ashland.

In some embodiments, vinylpyrrolidones (PVP) and their derivatives effectively enhance the adhesion of the compound of Formula I to plant leaves to improve adhesive and retention properties (e.g., rain resistance).

Sugar surfactants may include, but are not limited to, sorbitan esters, sucrose esters, alkyl polyglycosides, and fatty acid glucamides.

In some embodiments, the sugar surfactant is an alkyl or fatty acid derivative of glucamides.

In some embodiments, the sugar surfactant is an alkyl glucamide.

In some embodiments, the fatty acid glucamide is the C8/C10 fatty acid glucosamide.

In some embodiments, the C8/C10 fatty acid glucosamide is synergen GA from Clariant.

In some embodiments, the sugar surfactant is sorbitan and its derivatives.

In some embodiments, the sorbitan derivative is an ester of a polyethylene oxide derivative and a fatty acid.

In some embodiments, the sorbitan derivative is a di- or tri-ester with a fatty acid. In some embodiments, the sorbitan derivative is a polyethylene oxide derivative containing 20 to 80 ethylene oxide groups.

In some embodiments, the sorbitan derivative is Tween 80.

In some embodiments, the sugar surfactant affects the properties of the leaf by enhancing the penetration of the compound of Formula I through the leaf surface.

In some embodiments, the combination, mixture, or composition comprises a multiple adjuvant system. A multiple adjuvant system refers to a blend or any combination of adjuvants.

In some embodiments, the combination, mixture, or composition comprises at least two adjuvants. In some embodiments, the combination, mixture, or composition comprises at least three adjuvants.

In some embodiments, the adjuvant blend includes, but is not limited to, a combination of a fatty acid alkyl ester and a fatty alcohol alkoxylate.

In some embodiments, the combination of a fatty acid alkyl ester and a fatty alcohol alkoxylate is Synergen SOC, which is manufactured and sold by Clariant.

In some embodiments, the combination of a fatty acid alkyl ester and a fatty alcohol alkoxylate is FOP, which is manufactured and sold by Clariant.

In some embodiments, the adjuvant blend includes, but is not limited to, a combination of a vegetable oil and/or derivative thereof and a sugar surfactant.

In some embodiments, the combination, mixture, or composition comprises a pH adjuster.

In some embodiments, pH adjusters may include, but are not limited to, buffers, bases, and/or acidifiers.

In some embodiments, the pH adjuster is an acid. In some embodiments, the pH adjuster is a base.

In some embodiments, the pH adjuster is a mixture of at least one base and at least one acid.

In some embodiments, the pH adjuster is a buffer.

A buffer is a combination of acids and bases. Acids include (but are not limited to) organic and inorganic acids. Bases include (but are not limited to) organic and inorganic bases.

Organic acids may include (but are not limited to) citric acid, formic acid, acetic acid, propionic acid, butyric acid, oxalic acid, lactic acid, malic acid, and benzoic acid.

Inorganic acids may include (but are not limited to) hydrochloric acid, nitric acid, phosphoric acid, sulfuric acid, and boric acid.

Organic bases may include, but are not limited to, primary and secondary amines, pyridines, imidazole, and any combination thereof.

In some embodiments, the pH adjuster is potassium hydrogen phosphate.

In some embodiments, the pH adjuster is a combination of sodium monohydrogen phosphate and potassium hydrogen phosphate.

The present invention describes a composition comprising any of the combinations or mixtures of the present invention.

The present invention describes a fungicidal composition comprising: (i) a certain amount of a compound of formula I

and (ii) a certain amount of at least one fungicide (A) selected from the group consisting of fluindapyr, pydiflumetofen, mefentrifluconazole, inprifluxam, isofetamide and Qi-inhibitor.

The present invention describes a synergistic fungicidal composition comprising: (i) a certain amount of a compound of formula I

and (ii) a certain amount of at least one fungicide (A) selected from the group consisting of fluindapyr, pydiflumetofen, mefentrifluconazole, inprifluxam, isofetamide and Qi-inhibitor.

The present invention describes a fungicidal composition comprising: (i) a certain amount of a compound of formula I

and (ii) a certain amount of at least one fungicide (A) selected from the group consisting of fluindapyr, pidiflumetofen, mefentrifluconazole, inprifluxam, isofetamide and a Qi inhibitor,

where the composition is more effective in treating a plant or locus against a fungal infection than when each fungicide is applied separately in the same amount.

The present invention describes a fungicidal composition comprising: (i) a certain amount of a compound of formula I

and (ii) a certain amount of at least one fungicide (A) selected from the group consisting of fluindapyr, pidiflumetofen, mefentrifluconazole, inprifluxam, isofetamide and a Qi inhibitor,

wherein the amount of the compound of formula I and the amount of the fungicide (A) when applied together is more effective in treating the plant or locus against a fungal infection than when each fungicide in the same amount is applied separately.

The present invention describes a fungicidal composition comprising: (i) a certain amount of a compound of formula I

and (ii) a certain amount of at least one fungicide (A) selected from the group consisting of fluindapyr, pidiflumetofen, mefentrifluconazole, inprifluxam, isofetamide and a Qi inhibitor,

wherein the amount of the compound of formula I applied is less than the fungicidally effective amount of the compound of formula I when the compound of formula I is applied alone, and/or

where the applied amount of fungicide (A) is less than the fungicidally effective amount of fungicide (A) when fungicide (A) is applied alone.

In some embodiments, the composition comprises a compound of Formula I in an amount in the range of from about 0.1% to 90% by weight relative to the total weight of the composition, preferably from about 0.1% to 20% by weight relative to the total weight of the composition.

In some embodiments, the composition comprises a fungicide (A) in an amount in the range of from about 0.1% to 90% by weight relative to the total weight of the composition, preferably from about 0.1% to 20% by weight relative to the total weight of the composition.

In some embodiments, the amount of compound of Formula I in the composition is from about 0.1%, 0.5%, 1%, 1.5%, 2%, 2.5%, 3%, 3.5%, 4%, 4.5% or 5% to about 90%, 93%, 95%, 98% or 99% by weight relative to the total weight of the composition.

In some embodiments, the amount of fungicide (A) in the composition is from about 0.1%, 0.5%, 1%, 1.5%, 2%, 2.5%, 3%, 3.5%, 4%, 4.5% or 5% to about 90%, 93%, 95%, 98% or 99% by weight relative to the total weight of the composition.

In some embodiments, the amount of the compound of Formula I in the composition is about 0.1%, 0.5%, 1%, 1.5%, 2%, 2.5%, 3%, 3.5%, 4%, 4.5%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90%, or 95% by weight relative to the total weight of the composition.

In some embodiments, the amount of fungicide (A) in the composition is about 0.1%, 0.5%, 1%, 1.5%, 2%, 2.5%, 3%, 3.5%, 4%, 4.5%, 5%, 10%, 15%, 20%, 25%, 30%, 35%, 40%, 45%, 50%, 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90% or 95% by weight relative to the total weight of the composition.

In some embodiments, the weight ratio of the compound of Formula I and the fungicide (A) in the composition is in the range of about 400:1 to 1:100. In some embodiments, the weight ratio of the compound of Formula I and the fungicide (A) in the composition is in the range of about 200:1 to 1:100. In some embodiments, the weight ratio of the compound of Formula I and the fungicide (A) in the composition is in the range of about 50:1 to 1:50. In some embodiments, the weight ratio of the compound of Formula I and the fungicide (A) in the composition is in the range of about 200:1 to 1:100. In some embodiments, the weight ratio of the compound of Formula I and the fungicide (A) in the composition is in the range of about 10:1 to 1:10. In some embodiments, the weight ratio of the compound of Formula I and the fungicide (A) in the composition is in the range of about 5:1 to 1:5. In some embodiments, the weight ratio of the compound of Formula I to the fungicide (A) in the composition is in the range of from about 2:1 to 1:2.

In some embodiments, the weight ratio of the compound of Formula I and the fungicide (A) in the composition is from 5:1 to 30:1. In some embodiments, the weight ratio of the compound of Formula I and the fungicide (A) in the composition is from 10:1 to 30:1. In some embodiments, the weight ratio of the compound of Formula I and the fungicide (A) in the composition is from 25:1 to 12.5:1. In some embodiments, the weight ratio of the compound of Formula I and the fungicide (A) in the composition is 25:1. In some embodiments, the weight ratio of the compound of Formula I and the fungicide (A) in the composition is 12.5:1. In some embodiments, the weight ratio of the compound of Formula I and the fungicide (A) in the composition is 1:1.

In some embodiments, the composition further comprises a phytologically acceptable carrier.

In some embodiments, the composition further comprises a phytologically acceptable adjuvant.

In some embodiments, the composition further comprises at least one pesticide.

In some embodiments, the composition is incorporated into a preparation for dilution in water prior to use.

In some embodiments, the composition is a concentrated preparation that is dispersed in water or another liquid prior to use. In other embodiments, the composition is in the form of a powder or granules that can be used without further preparation. The compositions of the present invention can be prepared using methods well known in the field of agricultural chemistry, but are novel and important due to the synergistic effect they exhibit.

The compositions used are most often aqueous suspensions or emulsions. Such water-soluble, water-suspended, or water-emulsifiable formulations are solids, commonly referred to as wettable powders, or liquids, commonly referred to as emulsifiable concentrates, aqueous suspensions, or suspension concentrates. The present invention encompasses all carriers with which the synergistic compositions of the present invention can be mixed for delivery and use as a fungicide.

Wettable powders, which can be converted into compact water-dispersible granules, comprise a mixture of a synergistic composition, a carrier, and an agriculturally acceptable surfactant. The concentration of the composition of the present invention in the wettable powder is typically from about 10% to about 90% by weight, more preferably from about 25% to about 75% by weight, based on the total weight of the formulation. When preparing wettable powder formulations, the synergistic composition can be mixed with any finely divided solid.

Any material to which the compositions of the present invention can be added may be used, provided that they provide the required applicability without significantly affecting the activity of the synergistic mixtures or compositions as antifungal agents.

Methods of application

The present invention describes a method of treating a plant or locus against a fungal infection, comprising applying (i) a certain amount of a compound of formula I

and (ii) a determined amount of at least one fungicide (A) selected from the group consisting of fluindapyr, pydiflumetofen, mefentrifluconazole, inprifluxam, isofetamide and a Qi inhibitor, per plant or locus so as to treat the plant or locus against a fungal infection.

The present invention describes a method of treating a plant or locus against a fungal infection, comprising applying (i) a certain amount of a compound of formula I

and (ii) a certain amount of at least one fungicide (A) selected from the group consisting of fluindapyr, pydiflumetofen, mefentrifluconazole, inprifluxam, isofetamide and Qi-inhibitor, per plant or locus so as to treat the plant or locus against fungal infection,

where this method is more effective in treating a plant or locus against a fungal infection than when each fungicide is applied separately in the same amount.

The present invention describes a method of treating a plant or locus against a fungal infection, comprising applying (i) a certain amount of a compound of formula I

and (ii) a certain amount of at least one fungicide (A) selected from the group consisting of fluindapyr, pydiflumetofen, mefentrifluconazole, inprifluxam, isofetamide and Qi-inhibitor, per plant or locus so as to treat the plant or locus against fungal infection,

wherein the amount of the compound of formula I and the amount of the fungicide (A) when applied together is more effective in treating the plant or locus against a fungal infection than when each fungicide in the same amount is applied separately.

The present invention describes a method of treating a plant or locus against a fungal infection, comprising applying (i) a certain amount of a compound of formula I

and (ii) a certain amount of at least one fungicide (A) selected from the group consisting of fluindapyr, pydiflumetofen, mefentrifluconazole, inprifluxam, isofetamide and Qi-inhibitor, per plant or locus so as to treat the plant or locus against fungal infection,

wherein the amount of the compound of formula I applied is less than the fungicidally effective amount of the compound of formula I when the compound of formula I is applied alone, and/or

where the applied amount of fungicide (A) is less than the fungicidally effective amount of fungicide (A) when fungicide (A) is applied alone.

The present invention also describes a method of treating a plant or locus against a fungal infection, comprising applying an effective amount of any of the combinations, mixtures or compositions of the present invention to the plant or locus so as to treat the plant or locus against the fungal infection.

In some embodiments, the method is more effective in treating a plant or locus against a fungal infection than when each fungicide is applied separately in the same amount.

In some embodiments, the amount of the compound of formula I and the amount of the fungicide (A), when applied together, is more effective in treating a plant or locus against a fungal infection than when each fungicide is applied separately in the same amount.

In some embodiments, the applied amount of the compound of Formula I is less than the fungicidally effective amount of the compound of Formula I when the compound of Formula I is applied alone. In some embodiments, the applied amount of fungicide (A) is less than the fungicidally effective amount of fungicide (A) when fungicide (A) is applied alone.

In some embodiments, the method is effective for controlling a fungal infection of a plant or locus.

In some embodiments, controlling a fungal infection includes controlling a fungal disease affecting a plant or locus. In some embodiments, controlling a fungal infection includes controlling a plant or soil disease caused by phytopathological fungi. In some embodiments, controlling a fungal infection includes controlling a fungal attack on a plant or locus. In some embodiments, controlling a fungal infection includes reducing a fungal infection of a plant or locus. In some embodiments, controlling a fungal infection includes treating a plant or soil disease caused by phytopathological fungi.

In some embodiments, the method is effective for protecting a plant or locus from a fungal infection.

In some embodiments, protecting a plant or locus from a fungal infection includes protecting the plant or locus from attack by a fungus. In some embodiments, protecting a plant or locus from a fungal infection includes protecting the plant or locus from a fungal disease. In some embodiments, protecting a plant or locus from a fungal infection includes preventing fungal infection of the plant or locus.

In some embodiments, the method comprises applying an effective amount of any of the combinations, mixtures, or compositions of the present invention to plant propagation material. In some embodiments, the method comprises applying an effective amount of any of the combinations, mixtures, or compositions of the present invention to the seeds and/or seedlings of the plant.

In some embodiments, the method comprises the protective use of any of the combinations, mixtures, or compositions of the present invention. In some embodiments, the method comprises the therapeutic use of any of the combinations, mixtures, or compositions of the present invention.

In some embodiments, the method comprises protective application of a compound of Formula I and a fungicide (A). In some embodiments, the method comprises therapeutic application of a compound of Formula I and a fungicide (A).

In some embodiments, fungal attack is controlled by preventing the fungus from attacking the plant, seeds, or seedlings. In some embodiments, fungal attack is controlled by treating the fungus from attacking the plant, seeds, or seedlings.

The present invention also describes a method for controlling a plant disease caused by phytopathological fungi, comprising contacting a plant, plant propagation material or plant locus with an effective amount of any of the combinations of the present invention, to thereby control the plant disease.

The present invention also describes a method for controlling a fungal attack on a plant, seed or seedling, comprising applying any of the combinations of the present invention to the plant, seed, seedling and/or plant locus, to thereby treat or prevent a fungal attack on the plant, seed or seedling.

The present invention also describes a method for controlling a fungal attack on a plant, seed or seedling, comprising applying any of the compositions or mixtures of the present invention to a plant, seed, seedling and/or plant locus, to thereby control a fungal attack on the plant, seed or seedling.

The present invention also describes a method for treating a plant, seeds or seedlings to obtain a plant resistant to attack by a fungus, wherein said method comprises applying any of the compositions or mixtures of the present invention to a plant, seeds intended for growing a plant, seedlings intended for growing a plant, or a locus of a plant, to thereby obtain a plant resistant to attack by a fungus.

The present invention also describes a method for protecting a plant from attack by a fungus, wherein said method comprises applying any of the compositions or mixtures of the present invention to a plant, a locus of a plant, or seeds or seedlings intended for growing a plant, to thereby protect the plant from attack by a fungus.

The present invention also describes a plant resistant to attack by a fungus, wherein seeds intended for growing the plant, seedlings intended for growing the plant, or a locus of the plant are treated with any of the compositions or mixtures of the present invention.

The present invention also describes plant seeds or seedlings adapted to produce a plant resistant to fungal attack, wherein the plant seeds or seedlings are treated with any of the compositions or mixtures of the present invention.

The present invention also describes a method for controlling a fungal attack on a plant, comprising applying any of the compositions or mixtures of the present invention to the soil, plant, roots, leaves, seeds, locus of the fungus and/or the locus in which infection is to be prevented, to thereby control the fungal attack on the plant.

The present invention also describes a method for controlling fungal diseases of a plant and/or soil, comprising applying any of the compositions or mixtures of the present invention to the soil, plant, roots, leaves, seeds, locus of a fungus and/or locus in which infection is to be prevented, in order to counteract fungal diseases of a plant and/or soil.

The present invention also describes a method for controlling a plant disease caused by phytopathological fungi, comprising contacting a plant, plant propagation material or plant locus with (i) a certain amount of a compound of formula I

and (ii) a certain amount of at least one fungicide (A) selected from the group consisting of fluindapyr, pydiflumetofen, mefentrifluconazole, inprifluxam, isofetamide and Qi-inhibitor, to thereby control a plant disease.

In some embodiments, controlling a plant disease is accomplished by protecting the plant from the disease. In some embodiments, controlling a plant disease is accomplished by treating the plant disease.

The present invention also describes a method for controlling a fungal attack on a plant, seed or seedling, comprising applying to the plant, seed, seedling and/or locus of the plant (i) a certain amount of a compound of formula I

and (ii) a determined amount of at least one fungicide (A) selected from the group consisting of fluindapyr, pydiflumetofen, mefentrifluconazole, inprifluxam, isofetamide and a Qi inhibitor, to thereby control the attack of a fungus on a plant, seed or seedling.

In some embodiments, fungal attack is controlled by preventing the fungus from attacking the plant, seeds, or seedlings. In some embodiments, fungal attack is controlled by treating the fungus attack on the plant, seeds, or seedlings.

The present invention also describes a method for protecting a plant, seed or seedling from attack by a fungus, comprising applying to the plant, seed, seedling and/or locus of the plant (i) a certain amount of a compound of formula I

and (ii) a determined amount of at least one fungicide (A) selected from the group consisting of fluindapyr, pydiflumetofen, mefentrifluconazole, inprifluxam, isofetamide and a Qi inhibitor, to thereby protect the plant, seed or seedling from attack by the fungus.

In some embodiments, the method comprises protective application of a compound of Formula I and a fungicide (A). In some embodiments, the method comprises therapeutic application of a compound of Formula I and a fungicide (A).

In some embodiments, the method comprises applying a compound of Formula I and a fungicide (A) before the onset of a pathogenic fungal infection. In some embodiments, the method comprises applying a compound of Formula I and a fungicide (A) before the onset of symptoms of a pathogenic fungal infection. In some embodiments, the method comprises applying a compound of Formula I and a fungicide (A) when disease pressure is low.

In some embodiments, the method comprises applying a compound of Formula I and a fungicide (A) after the onset of a pathogenic fungal infection. In some embodiments, the method comprises applying a compound of Formula I and a fungicide (A) after the onset of symptoms of a pathogenic fungal infection.

In some embodiments, the method is effective in reducing leaf necrosis. In some embodiments, leaf necrosis is reduced by at least 10%. In some embodiments, leaf necrosis is reduced by at least 25%. In some embodiments, leaf necrosis is reduced by at least 50%. In some embodiments, leaf necrosis is reduced by at least 75%.

In some embodiments, the effectiveness of the method is assessed at least one week after application of the compound of Formula I and the fungicide (A). In some embodiments, the effectiveness of the method is assessed at least two weeks after application of the compound of Formula I and the fungicide (A). In some embodiments, the effectiveness of the method is assessed at least three weeks after application of the compound of Formula I and the fungicide (A). In some embodiments, the effectiveness of the method is assessed at least four weeks after application of the compound of Formula I and the fungicide (A).

In some embodiments, the compound of formula I and the fungicide (A) are used together.

In some embodiments, the compound of formula I and the fungicide (A) are applied simultaneously.

In some embodiments, the compound of Formula I and the fungicide (A) are applied sequentially.

In some embodiments, the compound of formula I and the fungicide (A) are used separately.

In some embodiments, the compound of Formula I and the fungicide (A) are used together.

In some embodiments, the compound of Formula I and the fungicide (A) are used together as a tank mix. In some embodiments, the compound of Formula I and the fungicide (A) are formulated into a single composition. In some embodiments, the compound of Formula I and the fungicide (A) are formulated into two separate compositions.

In some embodiments, the compound of Formula I and the fungicide (A) are used in the form of any of the combinations, mixtures or compositions of the present invention.

In some embodiments, the compound of Formula I and the fungicide (A) are applied to a part of a plant, to an area surrounding the plant, to soil in contact with the plant, to soil surrounding the plant, to any surface surrounding the plant, to any surface in contact with the plant, to seeds and/or to equipment used in agriculture. In some embodiments, the compound of Formula I and the fungicide (A) are applied to a locus of the plant, a locus in the immediate vicinity of the plant, a locus of the fungi, or a locus in the immediate vicinity of the fungi. In some embodiments, the compound of Formula I and the fungicide (A) are applied to the soil in which the plant grows. In some embodiments, the compound of Formula I and the fungicide (A) are applied to the soil in which the plant will grow.

In some embodiments, the compound of formula I and the fungicide (A) are applied at the time of planting.

In some embodiments, the compound of formula I and the fungicide (A) are applied between 1 and 60 days after planting.

In some embodiments, the compound of formula I and the fungicide (A) are applied between 1 and 9 months after planting.

In some embodiments, the compound of formula I and the fungicide (A) are applied once per growing season.

In some embodiments, the compound of Formula I and the fungicide (A) are applied at least once per growing season.

In some embodiments, the compound of Formula I and the fungicide (A) are applied two or more times per growing season.

In some embodiments, the compound of Formula I and fungicide (A) are applied to the soil. In some embodiments, the compound of Formula I and fungicide (A) are applied to the foliar surface.

In some embodiments, the compound of Formula I is used in an amount of 1 g/ha to 500 g/ha. In some embodiments, the compound of Formula I is used in an amount of 5 g/ha to 120 g/ha. In some embodiments, the compound of Formula I is used in an amount of 1 g/ha to 100 g/ha. In some embodiments, the compound of Formula I is used in an amount of 1 g/ha to 75 g/ha. In some embodiments, the compound of Formula I is used in an amount of 1 g/ha to 50 g/ha. In some embodiments, the compound of Formula I is used in an amount of 1 g/ha to 25 g/ha. In some embodiments, the compound of Formula I is used in an amount of 1 g/ha to 15 g/ha. In some embodiments, the compound of Formula I is used in an amount of 2 g/ha to 13 g/ha. In some embodiments, the compound of Formula I is used in an amount of 5 g/ha to 10 g/ha.

In some embodiments, the compound of Formula I is used in an amount of about 5 g/ha. In some embodiments, the compound of Formula I is used in an amount of about 6.25 g/ha. In some embodiments, the compound of Formula I is used in an amount of about 10 g/ha. In some embodiments, the compound of Formula I is used in an amount of about 12.5 g/ha. In some embodiments, the compound of Formula I is used in an amount of about 75 g/ha. In some embodiments, the compound of Formula I is used in an amount of about 100 g/ha. In some embodiments, the compound of Formula I is used in an amount of about 125 g/ha. In some embodiments, the compound of Formula I is used in an amount of about 150 g/ha. In some embodiments, the compound of Formula I is used in an amount of about 300 g/ha. In some embodiments, the compound of Formula I is used in an amount of about 500 g/ha.

In some embodiments, fungicide (A) is applied in an amount of 0.0001 g/ha to 500 g/ha. In some embodiments, fungicide (A) is applied in an amount of 0.1 g/ha to 100 g/ha. In some embodiments, fungicide (A) is applied in an amount of 0.1 g/ha to 75 g/ha. In some embodiments, fungicide (A) is applied in an amount of 0.1 g/ha to 50 g/ha. In some embodiments, fungicide (A) is applied in an amount of 0.1 g/ha to 25 g/ha. In some embodiments, fungicide (A) is applied in an amount of 0.1 g/ha to 10 g/ha. In some embodiments, fungicide (A) is applied in an amount of 0.1 g/ha to 5 g/ha. In some embodiments, fungicide (A) is applied in an amount of 0.1 g/ha to 0.7 g/ha. In some embodiments, fungicide (A) is applied in an amount of 0.0001 g/ha to 0.01 g/ha. In some embodiments, fungicide (A) is applied in an amount of 0.0003 g/ha to 0.008 g/ha. In some embodiments, fungicide (A) is applied in an amount of 0.1 g/ha to 150 g/ha. In some embodiments, fungicide (A) is applied in an amount of 0.1 g/ha to 1 g/ha.

In some embodiments, fungicide (A) is applied in an amount of about 0.0003 g/ha. In some embodiments, fungicide (A) is applied in an amount of about 0.001 g/ha. In some embodiments, fungicide (A) is applied in an amount of about 0.002 g/ha. In some embodiments, fungicide (A) is applied in an amount of about 0.008 g/ha. In some embodiments, fungicide (A) is applied in an amount of about 0.4 g/ha. In some embodiments, fungicide (A) is applied in an amount of about 6.25 g/ha. In some embodiments, fungicide (A) is applied in an amount of about 10 g/ha. In some embodiments, fungicide (A) is applied in an amount of about 12.5 g/ha. In some embodiments, fungicide (A) is applied in an amount of about 75 g/ha. In some embodiments, fungicide (A) is applied in an amount of about 100 g/ha. In some embodiments, fungicide (A) is applied in an amount of about 125 g/ha. In some embodiments, fungicide (A) is applied in an amount of about 150 g/ha. In some embodiments, fungicide (A) is applied in an amount of about 300 g/ha. In some embodiments, fungicide (A) is applied in an amount of about 500 g/ha.

In some embodiments, fluindapyr is used in an amount from 5 g/ha to 150 g/ha. In some embodiments, fluindapyr is used in an amount of from 0.1 g/ha to 150 g/ha. In some embodiments, fluindapyr is used in an amount of 0.1 g/ha to 1 g/ha. In some embodiments, fluindapyr is applied at an amount of about 0.4 g/ha.

In some embodiments, pydiflumetofen is applied in an amount of 0.0001 g/ha to 150 g/ha. In some embodiments, pydiflumetofen is applied in an amount of 0.0001 g/ha to 0.01 g/ha. In some embodiments, pydiflumetofen is applied in an amount of about 0.0003 g/ha. In some embodiments, pydiflumetofen is applied in an amount of about 0.001 g/ha. In some embodiments, pydiflumetofen is applied in an amount of about 0.002 g/ha. In some embodiments, pydiflumetofen is applied in an amount of about 0.008 g/ha.

In some embodiments, mefentrifluconazole is applied in an amount of 5 g/ha to 150 g/ha. In some embodiments, mefentrifluconazole is applied in an amount of 0.1 g/ha to 150 g/ha. In some embodiments, mefentrifluconazole is applied in an amount of 0.1 g/ha to 1 g/ha. In some embodiments, mefentrifluconazole is applied in an amount of about 0.4 g/ha.

In some embodiments, inprifluxam is applied in an amount of 5 g/ha to 150 g/ha. In some embodiments, inprifluxam is applied in an amount of 0.1 g/ha to 150 g/ha.

In some embodiments, isofetamide is used in an amount of from 5 g/ha to 150 g/ha. In some embodiments, isofetamide is used in an amount of from 0.1 g/ha to 150 g/ha.

In some embodiments, the Qi inhibitor is used in an amount of from 5 g/ha to 150 g/ha. In some embodiments, the Qi inhibitor is used in an amount of from 0.1 g/ha to 150 g/ha. In some embodiments, the Qi inhibitor is used in an amount of 0.1 g/ha to 1 g/ha. In some embodiments, the Qi inhibitor is applied at an amount of about 0.4 g/ha.

In some embodiments, fenpicoxamide is applied in an amount of 5 g/ha to 150 g/ha. In some embodiments, fenpicoxamide is applied in an amount of 0.1 g/ha to 150 g/ha. In some embodiments, fenpicoxamide is applied in an amount of 0.1 g/ha to 1 g/ha. In some embodiments, fenpicoxamide is applied in an amount of about 0.4 g/ha.

When the compound of formula I and the fungicide (A) are used in the form of combinations, mixtures, or compositions according to the present invention, the application rate of the combination, mixture, and/or composition depends on the specific fungal species being controlled, the desired degree of control, and the application schedule and method. In general, the combinations, mixtures, or compositions according to the present invention can be applied at a rate of from about 1 gram per hectare (g/ha) to about 2600 g/ha.

The combinations, mixtures or compositions of the present invention can be applied at a dosage of from about 40 g/ha to about 600 g/ha, based on the total weight of the active ingredients.

In some embodiments, a combination, mixture, or composition is used wherein the amount of the compound of Formula I is in the range of 1 g/ha to 500 g/ha. In some embodiments, a combination, mixture, or composition is used wherein the amount of the compound of Formula I is in the range of 5 g/ha to 120 g/ha. In some embodiments, a combination, mixture, or composition is used wherein the amount of the compound of Formula I is in the range of 1 g/ha to 100 g/ha. In some embodiments, a combination, mixture, or composition is used wherein the amount of the compound of Formula I is in the range of 1 g/ha to 75 g/ha. In some embodiments, a combination, mixture, or composition is used wherein the amount of the compound of Formula I is in the range of 1 g/ha to 50 g/ha. In some embodiments, a combination, mixture, or composition is used wherein the amount of the compound of Formula I is in the range of 1 g/ha to 25 g/ha. In some embodiments, a combination, mixture, or composition is used wherein the amount of the compound of Formula I is in the range of 1 g/ha to 15 g/ha. In some embodiments, a combination, mixture, or composition is used wherein the amount of the compound of Formula I is in the range of 2 g/ha to 13 g/ha. In some embodiments, a combination, mixture, or composition is used wherein the amount of the compound of Formula I is in the range of 5 g/ha to 10 g/ha.

In some embodiments, a combination, mixture, or composition is used wherein the amount of the compound of Formula I is about 5 g/ha. In some embodiments, a combination, mixture, or composition is used wherein the amount of the compound of Formula I is about 6.25 g/ha. In some embodiments, a combination, mixture, or composition is used wherein the amount of the compound of Formula I is about 10 g/ha. In some embodiments, a combination, mixture, or composition is used wherein the amount of the compound of Formula I is about 12.5 g/ha. In some embodiments, a combination, mixture, or composition is used wherein the amount of the compound of Formula I is about 75 g/ha. In some embodiments, a combination, mixture, or composition is used wherein the amount of the compound of Formula I is about 100 g/ha. In some embodiments, a combination, mixture, or composition is used wherein the amount of the compound of Formula I is about 125 g/ha. In some embodiments, a combination, mixture, or composition is used wherein the amount of the compound of Formula I is about 150 g/ha. In some embodiments, a combination, mixture, or composition is used wherein the amount of the compound of Formula I is about 300 g/ha. In some embodiments, a combination, mixture, or composition is used wherein the amount of the compound of Formula I is about 500 g/ha.

In some embodiments, a combination, mixture or composition is used wherein the amount of fungicide (A) is in the range of 1 g/ha to 500 g/ha.

In some embodiments, a combination, mixture, or composition is used wherein the amount of fungicide (A) is in the range of 0.1 g/ha to 100 g/ha. In some embodiments, a combination, mixture, or composition is used wherein the amount of fungicide (A) is in the range of 0.1 g/ha to 75 g/ha. In some embodiments, a combination, mixture, or composition is used wherein the amount of fungicide (A) is in the range of 0.1 g/ha to 50 g/ha. In some embodiments, a combination, mixture, or composition is used wherein the amount of fungicide (A) is in the range of 0.1 g/ha to 25 g/ha. In some embodiments, a combination, mixture, or composition is used wherein the amount of fungicide (A) is in the range of 0.1 g/ha to 10 g/ha. In some embodiments, a combination, mixture, or composition is used wherein the amount of fungicide (A) is in the range of 0.1 g/ha to 5 g/ha. In some embodiments, a combination, mixture, or composition is used wherein the amount of fungicide (A) is in the range of 0.1 g/ha to 0.7 g/ha.

In some embodiments, a combination, mixture, or composition is used wherein the amount of fungicide (A) is about 0.4 g/ha. In some embodiments, a combination, mixture, or composition is used wherein the amount of fungicide (A) is about 6.25 g/ha. In some embodiments, a combination, mixture, or composition is used wherein the amount of fungicide (A) is about 10 g/ha. In some embodiments, a combination, mixture, or composition is used wherein the amount of fungicide (A) is about 12.5 g/ha. In some embodiments, a combination, mixture, or composition is used wherein the amount of the compound of Formula I is about 75 g/ha. In some embodiments, a combination, mixture, or composition is used wherein the amount of fungicide (A) is about 100 g/ha. In some embodiments, a combination, mixture, or composition is used wherein the amount of fungicide (A) is about 125 g/ha. In some embodiments, a combination, mixture, or composition is used wherein the amount of fungicide (A) is about 150 g/ha. In some embodiments, a combination, mixture, or composition is used wherein the amount of fungicide (A) is about 300 g/ha. In some embodiments, a combination, mixture, or composition is used wherein the amount of fungicide (A) is about 500 g/ha.

The combinations, mixtures, and compositions of the present invention can be used to control and/or prevent various types of pathogenic fungi and associated diseases. In some embodiments, the pathogenic fungus is one of the following: Mycosphaerella graminicola, Septoria tritici, Puccinia triticina, Puccinia striiformis f. sp. tritici, Venturia inaequalis, Ustilago maydis, Uncinula necator, Rhynchosporium secalis, Magnaporthe grisea, Phakopsora pachyrhizi, Leptosphaeria nodorum, Blumeria graminis f. sp. tritici, Blumeria graminis f. sp. hordei, Erysiphe cichoracearum, Glomerella lagenarium, Cercospora beticola, Alternaria solani, Pyrenophora teres, Ramularia, Peronospora spp., Botrytis cinereal and Mycosphaerella fijiensis.

In some embodiments, the pathogenic fungus is Septoria. In some embodiments, the pathogenic fungus is Zymoseptoria tritici (SEPTTR). In some embodiments, the pathogenic fungus is Rhyncosporium. In some embodiments, the pathogenic fungus is Pyrenophora. In some embodiments, the pathogenic fungus is Microduchium majus. In some embodiments, the pathogenic fungus is Sclerotinia. In some embodiments, the pathogenic fungus is Cercosporea beticola.

In some embodiments, the fungal disease is one of the following: wheat leaf spot (Mycosphaerella graminicola; anamorph: Septoria tritici), wheat brown rust (Puccinia triticina), yellow rust (Puccinia striiformis f. sp. tritici), apple scab (Venturia inaequalis), corn smut (Ustilago maydis), grape powdery mildew (Uncinula necator), barley spot (Rhynchosporium secalis), rice blight (Magnaporthe grisea), rice rust (Phakopsora pachyrhizi), wheat glume septoria (Leptosphaeria nodorum), wheat powdery mildew (Blumeria graminis f. sp. tritici), barley powdery mildew (Blumeria graminis f. sp. hordei), powdery mildew of cucurbits (Erysiphe cichoracearum), anthracnose of cucurbits (Glomerella lagenarium), leaf spot of beet (Cercospora beticola), brown spot of tomato (Alternaria solani), net blotch of barley (Pyrenophora teres), downy mildew of vegetables (Peronospora spp.), downy mildew of cabbage (Peronospora spp.), downy mildew of cucurbits (Peronospora spp.), gray mold of grapes (Botrytis cinereal), gray mold of vegetables (Botrytis cinereal) and black sigatoka of bananas (Mycosphaerella fijiensis).

In some embodiments, the plant or soil disease is one of the following: leaf spot, brown rust, yellow rust, powdery mildew, downy mildew, gray mold, Asian soybean rust, and black sigatoka.

In some embodiments, the plant is a crop plant. The methods of the present invention can be applied to any crop plant, including but not limited to monocots such as sugarcane, rice, corn; or dicots such as beets (e.g., sugar beets or fodder beets); fruit crops (such as pome fruits, stone fruits, or berries, such as apples, pears, peaches, almonds, cherries, strawberries, raspberries, or blackcurrants); leguminous crop plants (such as beans, lentils, peas, or soybeans); oilseed crop plants (such as rapeseed, mustard, poppy, olives, sunflower, coconut, castor oil plant, cocoa beans, or peanuts); cucurbitaceous crop plants (such as squash, cucumbers, or melons); Fiber plants (such as cotton, flax, hemp, or jute); Citrus fruits (such as oranges, lemons, grapefruit, or tangerines); Vegetable crops (such as spinach, lettuce, cabbage, carrots, tomatoes, potatoes, pumpkins, or paprika); Bay plants (such as avocado, cinnamon, or camphor); Tobacco; Nuts; Coffee; Tea; Grapes; Hops; Durian; Bananas; Natural rubber plants; and Ornamental plants (such as flowers, shrubs, deciduous trees, or evergreens such as conifers).

In some embodiments, the plants are monocotyledons, more preferably cereal crops. In a particular embodiment, the cereal crop is wheat. In another particular embodiment, the cereal crop is triticale. In another particular embodiment, the cereal crop is rye. In another particular embodiment, the cereal crop is oats. In another embodiment, the cereal crop is barley. In another embodiment, the crop plants are rice. In another particular embodiment, the crop plants are sugarcane. In another embodiment, the crop plants are corn.

In another embodiment, the agricultural plants are dicotyledonous plants.

In one embodiment, the crop plant is oilseed rape.

The combination, mixture, or composition of the present invention may also be used to treat seeds to prevent or control phytopathogenic fungi, as described in U.S. Patent Application No. 2018-0000082 (published January 4, 2018), the entire contents of which are incorporated herein by reference.

In some embodiments, the combination, mixture, or composition of the present invention further comprises at least one additional pesticide. In some embodiments, the pesticide is a fungicide, herbicide, insecticide, acaricide, or nematicide.

In some embodiments, the combination, mixture, or composition of the present invention further comprises at least one fungicide.

In some embodiments, the fungicide is a fungicidal sterol biosynthesis inhibitor.

In some embodiments, the sterol biosynthesis inhibitor is selected from the group consisting of prothioconazole, epoxiconazole, cyproconazole, myclobutanil, prochloraz, metconazole, difenoconazole, tebuconazole, tetraconazole, fenbuconazole, propioconazole, fluquinconazole, flusilazole, flutriafol, and fenpropimorph.

In some embodiments, the sterol biosynthesis inhibitor is selected from the group consisting of prothioconazole, epoxiconazole, metconazole, difenoconazole, propioconazole, prochloraz, tetraconazole, tebuconazole, fenpropimorph, fenpropidin, ipconazole, triticonazole, spiroxamine, fenhexamide, and fenpyrazamine.

In some embodiments, the sterol biosynthesis inhibitor is prothioconazole. In some embodiments, the sterol biosynthesis inhibitor is epoxiconazole. In some embodiments, the sterol biosynthesis inhibitor is cyproconazole. In some embodiments, the sterol biosynthesis inhibitor is myclobutanil. In some embodiments, the sterol biosynthesis inhibitor is metconazole. In some embodiments, the sterol biosynthesis inhibitor is difenoconazole. In some embodiments, the sterol biosynthesis inhibitor is propioconazole. In some embodiments, the sterol biosynthesis inhibitor is prochloraz. In some embodiments, the sterol biosynthesis inhibitor is tetraconazole. In some embodiments, the sterol biosynthesis inhibitor is tebuconazole. In some embodiments, the sterol biosynthesis inhibitor is fluquinconazole. In some embodiments, the sterol biosynthesis inhibitor is flusilazole. In some embodiments, the sterol biosynthesis inhibitor is flutriafol. In some embodiments, the sterol biosynthesis inhibitor is fenpropimorph. In some embodiments, the sterol biosynthesis inhibitor is fenpropidin. In some embodiments, the sterol biosynthesis inhibitor is ipconazole. In some embodiments, the sterol biosynthesis inhibitor is triticonazole. In some embodiments, the sterol biosynthesis inhibitor is spiroxamine. In some embodiments, the sterol biosynthesis inhibitor is fenhexamid. In some embodiments, the sterol biosynthesis inhibitor is fenpyrazamine. In some embodiments, the sterol biosynthesis inhibitor is fenbuconazole.

In some embodiments, the fungicide is a succinate dehydrogenase inhibitor.

In some embodiments, the succinate dehydrogenase inhibitor is selected from the group consisting of benzovindiflupyr, penthiopyrad, isopyrazam, fluxapyroxad, boscalid, fluopyram, bixafen, and penflufen.

In some embodiments, the succinate dehydrogenase inhibitor is benzovindiflupyr. In some embodiments, the succinate dehydrogenase inhibitor is penthiopyrad. In some embodiments, the succinate dehydrogenase inhibitor is isopyrazam. In some embodiments, the succinate dehydrogenase inhibitor is fluxapyroxad. In some embodiments, the succinate dehydrogenase inhibitor is boscalid. In some embodiments, the succinate dehydrogenase inhibitor is fluopyram. In some embodiments, the succinate dehydrogenase inhibitor is bixafen. In some embodiments, the succinate dehydrogenase inhibitor is penflufen.

In some embodiments, the fungicide is a strobilurin fungicide.

In some embodiments, the strobilurin fungicide is selected from the group consisting of azoxytrobin, pyraclostrobin, picoxystrobin, fluoxastrobin, trifloxytrobin, kresoxim-methyl, dimoxystrobin, and orysastrobin.

In some embodiments, the strobilurin fungicide is azoxytrobin. In some embodiments, the strobilurin fungicide is pyraclostrobin. In some embodiments, the strobilurin fungicide is picoxystrobin. In some embodiments, the strobilurin fungicide is fluoxastrobin. In some embodiments, the strobilurin fungicide is trifloxytrobin. In some embodiments, the strobilurin fungicide is kresoxim-methyl. In some embodiments, the strobilurin fungicide is dimoxystrobin. In some embodiments, the strobilurin fungicide is orysastrobin.

In some embodiments, the fungicide is a fungicidal multisite inhibitor.

In some embodiments, the fungicidal multisite inhibitor is selected from the group consisting of mancozeb, chlorothalonil, folpet, captan, metiram, maneb, propineb, copper hydroxide, copper octanoate, copper oxychloride, copper sulfate, copper sulfate (tribasic), mancopper, copper oxinate, copper bis(3-phenylsalicylate), copper zinc chromate, copper oxide, copper hydrazine sulfate, and cuprobam.

In some embodiments, the fungicidal multisite inhibitor is mancozeb. In some embodiments, the fungicidal multisite inhibitor is chlorothalonil. In some embodiments, the fungicidal multisite inhibitor is folpet. In some embodiments, the fungicidal multisite inhibitor is captan. In some embodiments, the fungicidal multisite inhibitor is metiram. In some embodiments, the fungicidal multisite inhibitor is maneb. In some embodiments, the fungicidal multisite inhibitor is propineb. In some embodiments, the fungicidal multisite inhibitor is copper hydroxide, copper octanoate, copper oxychloride, copper sulfate, copper sulfate (tribasic), mancopper, copper oxinate, copper bis(3-phenylsalicylate), copper zinc chromate, copper oxide, copper hydrazine sulfate, or cuprobam.

In some embodiments, the combination, mixture, or composition of the present invention further comprises a pesticide.

In some embodiments, the pesticide is selected from the group consisting of the following compounds: 2-(thiocyanatomethylthio)-benzothiazole, 2-phenylphenol, 8-hydroxyquinoline sulfate, amethocradine, amisulbrom, antimycin, Ampelomyces quisqualis, azaconazole, azoxytrobin, Bacillus subtilis, Bacillus subtilis line QST713, benalaxyl, benomyl, benthiavalicarb-isopropyl, benzylaminobenzene sulfonate (BABS) salt, bicarbonates, biphenyl, bismerthiazole, bitertanol, bixafen, blasticidin-S, borax, Bordeaux mixture, boscalid, bromucunazole, bupirimate, calcium polysulfide, captafol, captan, carbendazim, carboxin, carpropamide, carvone, Chlazafenone, Chlorneb, Chlorthalonil, Chlozolinate, Coniothyrium minitans, Copper Hydroxide, Copper Octanoate, Copper Oxychloride, Copper Sulfate, Copper Sulfate (Tribasic), Copper Oxide, Cyazofamid, Cyflufenamid, Cymoxanil, Cyproconazole, Cyprodinil, Dazomet, Debacarb, Diammonium Ethylenebis-(Dithiocarbamate), Dichlofluanid, Dichlorfen, Diclocymet, Dichloran, Diethofencarb, Difenoconazole, Difenzoquat ion, Diflumetorim, Dimethomorph, Dimoxystrobin, Diniconazole, Diniconazole-M, Dinobuton, Dinocap, Diphenylamine, Dithianon, Dodemorph, Dodemorph Acetate, Dodine, Dodine Free Base, Edifenphos, enestrobin, enestroburin, epoxiconazole, etaboxam, ethoxyquin, etridiazole, famoxadone, fenamidone, fenarimol, fenbuconazole, fenfuram, fenhexamide, fenoxanil, fenpiclonil, fenpropidine, fenpropimorph, fenpyrazamine, fentin, fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, fludoxonil, flumorph, fluopicolide, fluopyram, fluorimide, fluoxastrobin, fluquinconazole, flusilazole, flusulfamide, flutianil, flutolanil, flutriafol, fluxapyroxad, folpet, formaldehyde, fosetil, fosetyl-aluminium, fuberidazole, furalaxyl, furamethpyr, Guazatine, Guazatine acetates, GY-81, hexachlorobenzene, hexaconazole, hymexazole, imazalil, imazalil sulfate, imibenconazole, iminoctadine, iminoctadine triacetate, iminoctadine tris(albesylate), iodocarb, ipconazole, ipfenpyrazolone, iprobenfos, iprodione, iprovalicarb, isoprothiolane, isopyrazam, isothianil, kasugamycin, kasugamycin hydrochloride hydrate, kresoxim-methyl, laminarin, mancopper, mancozeb, mandipropamide, maneb, mefenoxam, mepanipyrim, mepronil, meptyl-dinocap, mercuric chloride (I), mercuric oxide, mercuric chloride (I), metalaxyl, metalaxyl-M, metam, Metam Ammonium, Metam Potassium, Metam Sodium, Metconazole, Metasulfacarb, Methyl Iodide, Methyl Isothiocyanate, Metiram, Metominostrobin, Metrafenone, Mildiomycin, Myclobutanil, Nabam, Nitrothal Isopropyl, Nuarimol, Octylion, Ofurace, Oleic Acid (Fatty Acids), Orysastrobin, Oxadixyl, Copper Oxynate, Oxpoconazole Fumarate, Oxycarboxin, Pefurazoate, Penconazole, Pencycuron, Penflufen, Pentachlorophenol, Pentachlorophenyl Laurate, Penthiopyrad, Phenylmercuric Acetate, Phosphonic Acid, Phthalide, Picoxystrobin, Polyoxin B, Polyoxins, Polyoxorim, Potassium Bicarbonate, Hydroxyquinoline Potassium Sulfate, Probenazole, Prochloraz, Procymidone, Propamocarb, Propamocarb Hydrochloride, Propioconazole, Propineb, Proquinazid, Prothioconazole, Pyraclostrobin, Pyramethostrobin, Pyraoxystrobin, Pyrazophos, Pyribencarb, Pyributicarb, Pyrifenox, Pyrimethanil, Pyriophenone, Pyroquilone, Quinoclamine, Quinoxyfen, Quintozene, Reynoutria sachalinensis Extract, Sedaxan, Silthiofam, Simeconazole, Sodium 2-Phenylphenoxide, Sodium Bicarbonate, Sodium Pentachlorophenoxide, Spiroxamine, Sulfur, SYP-Z048, Coal Oil, Tebuconazole, Tebufloquine, Tecnazen, Tetraconazole, Thiabendazole, Thifluzamide, Thiophanate-methyl, Thiram, Tiadinil, Tolclofos-methyl, Tolylfluanid, Triadimefon, Triadimenol, Triazoxide, Tricyclazole, Tridemorph, Trifloxytrobin, Triflumizole, Triforine, Triticonazole, Validamycin, Valifenalate, Valifenal, Vinclozolin, Zineb, Ziram, Zoxamide, Candida oleophila, Fusarium oxysporum, Gliocladium species, Phlebiopsis gigantea, Streptomyces griseoviridis, Trichoderma species, (RS)-N-(3,5-dichlorophenyl)-2-(methoxymethyl)-succinimide, 1,2-dichloropropane, 1,3-dichloro-1,1,3,3-tetrafluoroacetone hydrate, 1-chloro-2,4-dinitronaphthalene, 1-chloro-2-nitropropane, 2-(2-heptadecyl-2-imidazolin-1-yl)ethanol, 2,3-dihydro-5-phenyl-1,4-dithiin 1,1,4,4-tetroxide, 2-methoxyethylmercuric acetate, 2-methoxyethylmercuric chloride, 2-methoxyethylmercuric silicate, 3-(4-chlorophenyl)-5-methylrhodanine, 4-(2-nitroprop-1-enyl)phenyl thiocyanate, ampropylphos, anilazine, azitiram, barium polysulfide, Bayer 32394, benodanil, benquinox, benthaluron, benzamacryl, benzamacryl isobutyl, benzamorph, binapacryl, bis(methylmercuric) sulfate, bis(tributyltin) oxide, bithiobate, cadmium calcium chromate, Copper-zinc sulfate, carbamorph, CECA, chlobenthiazone, chloraniformethane, chlorphenazole, chlorquinox, climbazole, copper bis(3-phenylsalicylate), copper-zinc chromate, cufraneb, copper-hydrazine sulfate, cuprobam, cyclafuramide, cypendazole, ciprofuram, decafentin, dichlon, dichlozolin, diclobutrazol, dimethirimol, dinocton, dinosulfone, dinoterbon, dipyrithione, ditalimphos, dodicin, drazoxolone, EBP, ESBP, etaconazole, ethem, ethirim, fenaminosulf, fenapanil, fenitropan, fluotrimazole, furcarbanil, furconazole, furconazole-cis, furmecyclox, furofanate, Gliodin, Griseofulvin, Galacrinate, Hercules 3944, Hexythiophos, ICIA0858, Isopamphos, Isovaledione, Mebenil, Mecarbinside, Metazoxolone, Metfuroxam, Methylmercuric Dicyandiamide, Metsulfovax, Milneb, Mucochloric Anhydride, Myclozolin, N-3,5-Dichlorophenyl Succinimide, N-3-Nitrophenyl Itaconimide, Natamycin, N-Ethymercuric-4-Toluenesulfonamide, Nickel Bis(Dimethyldithiocarbamate), OCH, Phenylmercuric Dimethyldithiocarbamate, Phenylmercuric Nitrate, Phosphdifen, Prothiocarb, Prothiocarb Hydrochloride, Pyracarbolide, Pyridinitrile, Pyroxychlor, Pyroxyfur, Quinacetol, quinacetol sulfate, quinazamide, quinconazole, rabenzazole, salicylanilide, SSF-109, sultropen, tecoram, tiadiflor, ticiofen, thiochlorfenfim, thiophanate, thioquinox, thioximide, triamiphos, triarimol, triazbutyl, trichlamide, urbacid, zarilamide and any combinations thereof.

In some embodiments, the pesticide is an insecticide. In some embodiments, the pesticide is an acaricide. In some embodiments, the pesticide is a nematicide. In some embodiments, the pesticide is a herbicide.

Examples of insecticides and acaricides include (but are not limited to) abamectin, pyriproxyfen, acetamiprid, bifenthrin, cyfluthrin, pymetrozine, novaluron, ethiprole, fipronil, and lambda-cyhalothrin.

An example of a nematicide includes (but is not limited to) fluensulfone.

The combination, mixture, or composition of the present invention can be applied to fungi or their loci. Application can be accomplished using standard sprayers, granule applicators, and other commonly used methods familiar to those skilled in the art.

Each embodiment described herein may be applied to any other embodiment of the present invention. Thus, all combinations of the various elements described herein are within the scope of the present invention. Furthermore, the elements described in the combination embodiments may be applied in the mixture, composition, and method embodiments described herein, and vice versa.

Calculating synergies

A synergistic effect is observed when the effect of a combination of active substances is stronger than the combined effect of the individual components.

In the field of agriculture, the term "synergy" is often understood as defined by Colby S. R. in the article entitled "Calculation of the synergistic and antagonistic responses of herbicide combinations", published in the journal Weeds, 1967, 15, pp. 20-22. The action expected for a given combination of two active substances can be calculated as follows:

Where E is the expected percentage of insecticidal efficacy for a combination of two active ingredients at specific dosages (e.g., x and y, respectively), X is the percentage of insecticidal efficacy observed for compound (I) at a specific dosage (equivalent to x), and Y is the percentage of insecticidal efficacy observed for compound (II) at a specific dosage (equivalent to y). When the percentage of insecticidal efficacy observed for a combination is higher than the expected percentage of efficacy, a synergistic effect occurs.

Although the subject matter of the present invention has been shown and described in connection with its preferred embodiments, those skilled in the art will recognize that many alternatives, modifications, and variations can be made thereto without departing from the spirit and scope of the invention. Accordingly, the invention embraces all such alternatives, modifications, and variations that fall within the scope of the appended claims.

All publications, patents, and patent applications mentioned in this specification are herein incorporated by reference in their entirety to the same extent as if each individual publication, patent, or patent application were expressly indicated to be incorporated by reference.

The examples described below illustrate the practical implementation of the subject matter of the present invention in some of its embodiments and should not be construed as limiting the scope of the present invention. Other embodiments will be apparent to those skilled in the art upon studying the specification and the given examples. This specification, including the examples, is illustrative only and does not limit the spirit and scope of the present invention.

Experimental part

Materials and methods

The compound of formula I can be prepared as described in WO2015/103144 and WO2015/103142.

Pidiflumetofen (ADEPYDIN®, Syngenta) - 0.05% in Tween 80.

Fluindapyr - 0.05% in Tween 80

Mefentrifluconazole - 0.05% in Tween 80

Fenpicoxamide - 0.05% in Tween 80

Inprifluxam - 0.05% in Tween 80

Isofetamide - 0.05% in Tween 80

Winter wheat cv. Alixan (Limagrain) at the BBCH 12 growth stage is treated with a mixture of a compound of formula I and a fungicide selected from the group consisting of fluindapyr, pydiflumetofen, mefentrifluconazole, fenpicoxamide, inprifluxam and isofetamide.

The compound of formula I and fungicide (A) were applied at different doses and in various weight ratios using a hand-held sprayer calibrated to a pressure of 2 bar. Three replicates (pots) of six wheat plants were used for each set of tests.

Fragments of the first leaf were cut and transferred to a Petri dish containing adapted water agar (6 leaf fragments per Petri dish). The fragments were inoculated with a calibrated pycnospore suspension of Z. tritici line Mg Tri-R6.

After inoculation, the Petri dishes were incubated in a climate chamber at a temperature of 20°C day/17°C night, with a photoperiod of 16 hours light/8 hours dark, and controlled relative humidity. Disease assessment was performed 21 days after inoculation and 28 days after inoculation, measuring the length of the leaf fragment affected by necrosis. Infection intensity was then calculated as a percentage of the total leaf fragment length.

Efficacy was calculated using the area under the disease progression curve (AUC), which is a quantitative measure of disease intensity over time. The most commonly used method for estimating AUC, the trapezoidal method, is applied for each time interval by multiplying the average disease intensity between each pair of adjacent time points by the corresponding time interval.

The effectiveness of fungicides is determined by the values of the PCRB and is expressed as a percentage of the control (without treatment).

Example 1. Synergistic test of a mixture of a compound of formula I and mefentrifluconazole

The compound of formula I and mefentrifluconazole were administered according to Table 1 below.

Table 1. Dosage rates for the compound of formula I and mefentrifluconazole

Group Consumption rate Without processing - Compound of formula I 5 g active ingredient/ha Compound of formula I 10 g active ingredient/ha Mefentrifluconazole 0.39 g active ingredient/ha Compound of formula I + mefentrifluconazole 5 g active ingredient/ha (compound of formula I) + 0.39 g active ingredient/ha (mefentrifluconazole) Compound of formula I + mefentrifluconazole 10 g active ingredient/ha (compound of formula I) + 0.39 g active ingredient/ha (mefentrifluconazole)

The compound of formula I and mefentrifluconazole were applied using a hand-held sprayer at 2 bar pressure, calibrated to deliver a dose equivalent to 200 l/ha. Three replicates (pots) of six wheat plants each were used for each test group.

Fragments of the first leaf were cut and transferred to a Petri dish containing adapted water agar (6 leaf fragments per Petri dish). The fragments were inoculated with a calibrated pycnospore suspension of Z. tritici line Mg Tri-R6.

After inoculation, the Petri dishes were incubated in a climate chamber at a temperature of 20°C day/17°C night, with a photoperiod of 16 hours light/8 hours dark, and controlled relative humidity. Disease assessment was performed 21 days after inoculation and 28 days after inoculation, measuring the length of the leaf fragment affected by necrosis. Infection intensity was then calculated as a percentage of the total leaf fragment length.

Efficacy was calculated using the area under the disease progression curve (AUC), which is a quantitative measure of disease intensity over time. The most commonly used method for estimating AUC, the trapezoidal method, was applied for each time interval by multiplying the average disease intensity between each pair of adjacent time points by the corresponding time interval.

The effectiveness of fungicides was determined by the values of the PCRB and expressed as a percentage of the control (no treatment).

The results obtained are shown in Table 2 and Fig. 1.

Table 2. Efficacy of the compound of formula I and mefentrifluconazole when applied alone or as a binary mixture on Z. tritici strain Mg Tri-R6.

Processing Dosage
(g active ingredient/ha) Observed effectiveness Expected effectiveness Synergy factor Compound of formula I 5 56.4% - - 10 69.1% - - Mefentrifluconazole 0.39 46.8% - - Mefentrifluconazole + Compound of Formula I 0.39 + 5 94.5% 76.8% 1.23 0.39 + 10 97.3% 83.6% 1.16

^α Synergy factor = Observed efficacy/Expected efficacy.

Example 2. Synergistic test of a mixture of a compound of formula I and fenpicoxamide

The compound of formula I and fenpicoxamide were used according to Table 3 below.

Table 3. Consumption rates of the compound of formula I and fenpicoxamide

Group Consumption rate Without processing - Compound of formula I 5 g active ingredient/ha Compound of formula I 10 g active ingredient/ha Fenpicoxamide 0.39 g active ingredient/ha Compound of formula I + fenpicoxamide 5 g active ingredient/ha (compound of formula I) + 0.39 g active ingredient/ha (fenpicoxamide) Compound of formula I + fenpicoxamide 10 g active ingredient/ha (compound of formula I) + 0.39 g active ingredient/ha (fenpicoxamide)

The compound of formula I and fenpicoxamide were applied using a hand-held sprayer at 2 bar pressure, calibrated to a dose equivalent to 200 l/ha. Three replicates (pots) of six wheat plants each were used for each test group.

Fragments of the first leaf were cut and transferred to a Petri dish containing adapted water agar (6 leaf fragments per Petri dish). The fragments were inoculated with a calibrated pycnospore suspension of Z. tritici line Mg Tri-R6.

After inoculation, the Petri dishes were incubated in a climate chamber at a temperature of 20°C day/17°C night, with a photoperiod of 16 hours light/8 hours dark, and controlled relative humidity. Disease assessment was performed 21 days after inoculation and 28 days after inoculation, measuring the length of the leaf fragment affected by necrosis. Infection intensity was then calculated as a percentage of the total leaf fragment length.

Efficacy was calculated using the area under the disease progression curve (AUC), which is a quantitative measure of disease intensity over time. The most commonly used method for estimating AUC, the trapezoidal method, was applied for each time interval by multiplying the average disease intensity between each pair of adjacent time points by the corresponding time interval.

The effectiveness of fungicides was determined by the values of the PCRB and expressed as a percentage of the control (no treatment).

The results obtained are shown in Table 4 and Fig. 2.

Table 4. Efficacy of the compound of formula I and fenpicoxamide when used alone or as part of a two-component mixture against Z. tritici line Mg Tri-R6.

Processing Dosage
(g active ingredient/ha) Observed effectiveness Expected effectiveness Synergy factor Compound of formula I 5 56.4% - 10 69.1% - Fenpicoxamide 0.39 56.0% - Phenpicoxamide + Compound of Formula I 0.39 + 5 92.5% 80.8% 1.14 0.39 + 10 94.8% 86.4% 1.10

^α Synergy factor = Observed efficacy/Expected efficacy.

Example 3. Synergy test of a mixture of a compound of formula I and fluindapyr

The compound of formula I and fluindapyr were administered according to Table 5 below.

Table 5. Consumption rates of the compound of formula I and fluindapyr

Group Consumption rate Without processing - Compound of formula I 5 g active ingredient/ha Compound of formula I 10 g active ingredient/ha Fluindapir 0.39 g active ingredient/ha Compound of formula I + fluindapyr 5 g active ingredient/ha (compound of formula I) + 0.39 g active ingredient/ha (fluindapyr) Compound of formula I + fluindapyr 10 g active ingredient/ha (compound of formula I) + 0.39 g active ingredient/ha (fluindapyr)

The compound of formula I and fluindapyr were applied using a hand-held sprayer at 2 bar pressure, calibrated to deliver a dose equivalent to 200 l/ha. Three replicates (pots) of six wheat plants each were used for each test group.

Fragments of the first leaf were cut and transferred to a Petri dish containing adapted water agar (6 leaf fragments per Petri dish). The fragments were inoculated with a calibrated pycnospore suspension of Z. tritici line Mg Tri-R6.

After inoculation, the Petri dishes were incubated in a climate chamber at a temperature of 20°C day/17°C night, with a photoperiod of 16 hours light/8 hours dark, and controlled relative humidity. Disease assessment was performed 21 days after inoculation and 28 days after inoculation, measuring the length of the leaf fragment affected by necrosis. Infection intensity was then calculated as a percentage of the total leaf fragment length.

Efficacy was calculated using the area under the disease progression curve (AUC), which is a quantitative measure of disease intensity over time. The most commonly used method for estimating AUC, the trapezoidal method, was applied for each time interval by multiplying the average disease intensity between each pair of adjacent time points by the corresponding time interval.

The effectiveness of fungicides was determined by the values of the PCRB and expressed as a percentage of the control (no treatment).

The results obtained are shown in Table 6 and Fig. 3.

Table 6. Efficacy of the compound of formula I and fluindapyr when used alone or as part of a two-component mixture against Z. tritici line Mg Tri-R6.

Processing Dosage
(g active ingredient/ha) Observed effectiveness Expected effectiveness Synergy factor Compound of formula I 5 56.4% - 10 69.1% - Fluindapir 0.39 43.5% - Fluindapyr + Compound of Formula I 0.39 + 5 93.3% 75.4% 1.24 0.39 + 10 88.9% 82.6% 1.08

^α Synergy factor = Observed efficacy/Expected efficacy.

Example 4. Synergistic test of a mixture of a compound of formula I and pydiflumetofen

Winter wheat plants cv. Alixan (Limagrain) at the BBCH 12 growth stage were treated with a mixture of the compound of formula I and pidiflumetofen at several rates using a hand-held sprayer with a pressure of 2 bar, calibrated to a dose equivalent to 200 l/ha. The compound of formula I was applied at a dose of 5 g active ingredient/ha. Pidiflumetofen was applied at a dose of 0.00032–0.0016 and 0.008 g active ingredient/ha. Three replicates (pots) of six wheat plants each were used for each test group.

After treatment, the wheat plants were left to dry at room temperature for 1 hour and then incubated in a climate chamber at 24°C day/18°C night, with a photoperiod of 16 hours light/8 hours dark, and a relative humidity of 65%. Fragments of the first leaf were cut and transferred to a Petri dish containing adapted water agar (6 leaf fragments per Petri dish). The fragments were inoculated with a calibrated pycnospore suspension of Z. tritici line Mg Tri-R6.

After inoculation, Petri dishes were incubated in a climate chamber with a temperature of 20°C day/17°C night, a photoperiod of 16 h light/8 h dark, and controlled relative humidity.

Disease assessment was performed 21 days after inoculation and 28 days after inoculation, measuring the length of the leaf fragment affected by necrosis. Infection intensity was then calculated as a percentage of the total leaf fragment length.

Efficacy was calculated using the area under the disease progression curve (AUC), which is a quantitative measure of disease intensity over time. The most commonly used method for estimating AUC, the trapezoidal method, was applied for each time interval by multiplying the average disease intensity between each pair of adjacent time points by the corresponding time interval.

The effectiveness of fungicides was determined by the values of the PCRB and expressed as a percentage of the control (no treatment).

The results obtained are shown in Table 7 and Fig. 4.

Table 7. Efficacy of the compound of formula I and pydiflumetofen when used alone or as part of a two-component mixture against Z. tritici line Mg Tri-R6.

Processing Dosage
(g active ingredient/ha) Observed effectiveness Expected effectiveness Synergy factor Compound of formula I 5 63.2% - - Pidiflumetofen 0.00032 21.3% 0.0016 35.6% 0.008 44.0% - - Pidiflumetofen + Compound of Formula I 0.00032 + 5 84.7% 71.0% 1.19 0.0016 + 5 87.3% 76.3% 1.14 0.008 + 5 91.4% 79.4% 1.15

^α Synergy factor = Observed efficacy/Expected efficacy.

Example 5. Synergistic test of a mixture of a compound of formula I and inprifluxam

Winter wheat plants (cv. Alixan (Limagrain)) at the BBCH 12 growth stage were treated with a mixture of Formula I and inprifluxam at several rates using a handheld sprayer with a pressure of 2 bar, calibrated to deliver a dose equivalent to 200 l/ha. Three replicates (pots) of six wheat plants each were used for each test group.

Fragments of the first leaf were cut and transferred to a Petri dish containing adapted water agar (6 leaf fragments per Petri dish). The fragments were inoculated with a calibrated pycnospore suspension of Z. tritici line Mg Tri-R6.

After inoculation, Petri dishes were incubated in a climate chamber with a temperature of 20°C day/17°C night, a photoperiod of 16 h light/8 h dark, and controlled relative humidity.

Disease assessment was performed 21 days after inoculation and 28 days after inoculation, measuring the length of the leaf fragment affected by necrosis. Infection intensity was then calculated as a percentage of the total leaf fragment length.

Efficacy was calculated using the area under the disease progression curve (AUC), which is a quantitative measure of disease intensity over time. The most commonly used method for estimating AUC, the trapezoidal method, was applied for each time interval by multiplying the average disease intensity between each pair of adjacent time points by the corresponding time interval.

The effectiveness of fungicides was determined by the values of the PCRB and expressed as a percentage of the control (no treatment).

The results obtained show that the binary mixture of the compound of formula I and inprifluxam has a synergistic effect against Z. tritici line Mg Tri-R6.

Example 6. Synergistic test of a mixture of a compound of formula I and isofetamide

Winter wheat plants (cv. Alixan (Limagrain)) at the BBCH 12 growth stage were treated with a mixture of Formula I and isofetamide at several rates using a handheld sprayer with a pressure of 2 bar, calibrated for a dose equivalent to 200 l/ha. Three replicates (pots) of six wheat plants each were used for each test group.

Fragments of the first leaf were cut and transferred to a Petri dish containing adapted water agar (6 leaf fragments per Petri dish). The fragments were inoculated with a calibrated pycnospore suspension of Z. tritici line Mg Tri-R6.

After inoculation, the Petri dishes were incubated in a climate chamber at a temperature of 20°C day/17°C night, with a photoperiod of 16 hours light/8 hours dark, and controlled relative humidity. Disease assessment was performed 21 days after inoculation and 28 days after inoculation, measuring the length of the leaf fragment affected by necrosis. Infection intensity was then calculated as a percentage of the total leaf fragment length.

Efficacy was calculated using the area under the disease progression curve (AUC), which is a quantitative measure of disease intensity over time. The most commonly used method for estimating AUC, the trapezoidal method, was applied for each time interval by multiplying the average disease intensity between each pair of adjacent time points by the corresponding time interval.

The effectiveness of fungicides was determined by the values of the PCRB and expressed as a percentage of the control (no treatment).

The results obtained show that the binary mixture of the compound of formula I and isofetamide exerts a synergistic effect against Z. tritici line Mg Tri-R6.

Conclusions

It has been shown that combinations of a compound of formula I with a fungicide (A), wherein the fungicide (A) is selected from the group consisting of fluindapyr, pydiflumetofen, mefentrifluconazole, fenpicoxamide, inprifluxam and isofetamide, exhibit a strong synergistic effect.

Claims (46)

1. A fungicidal combination containing: (i) an effective amount of a compound of formula I and (ii) an effective amount of a fungicide (A) selected from fluindapyr, wherein the weight ratio of the compound of formula I and the fungicide (A) is from 10:1 to 1:10. 2. The combination according to claim 1, further comprising at least one pesticide, at least one stabilizing surfactant and/or at least one phytologically acceptable adjuvant. 3. The combination according to paragraph 1, characterized in that it is a tank mixture. 4. A combination according to any one of paragraphs 1-3, characterized in that it is used to treat a plant or a locus of a plant against a fungal infection. 5. A synergistic fungicidal composition comprising a combination according to any one of claims 1-4 and a phytologically acceptable carrier. 6. The composition according to item 5, where: a) the composition comprises a compound of formula I in an amount in the range of 0.1 to 90% by weight relative to the total weight of the composition, and/or b) the composition contains a fungicide (A) in an amount in the range from 0.1 to 90% by weight relative to the total weight of the composition. 7. The composition according to claim 5 or 6, characterized in that it is used to treat a plant or a locus of a plant from a fungal infection. 8. A method for treating a plant or plant locus, plant propagation material, plant seeds and/or seedlings, and/or soil against a fungal infection, comprising applying an effective amount of a combination according to any one of claims 1-4 or a composition according to claim 5 or 6 to a plant or plant locus, plant propagation material, plant seeds and/or seedlings, and/or soil. 9. The method according to paragraph 8, where: a) the compound of formula I is applied in an amount of 1 g/ha to 500 g/ha, and/or b) fungicide (A) is applied in quantities from 0.1 g/ha to 500 g/ha. 10. The method according to claim 8 or 9, wherein the compound of formula I is applied in an amount of 5 g/ha or 10 g/ha. 11. The method according to any of paragraphs 8-10, where: Fluindapyr is used in quantities ranging from 0.1 g/ha to 150 g/ha. 12. A method for controlling a plant disease caused by phytopathological fungi, comprising contacting the plant or a locus of the plant with an effective amount of a combination according to any one of claims 1-4 or a composition according to claim 5 or 6. 13. A method for controlling a fungal attack on a plant, seeds or seedlings, comprising applying a combination according to any one of claims 1-4 or a composition according to claim 5 or 6 to the plant, seeds, seedlings and/or plant locus. 14. A method of treating a plant, a plant locus, seeds or seedlings to obtain a plant resistant to attack by a fungus, wherein said method comprises applying a combination according to any one of claims 1-4 or a composition according to claim 5 or 6 to the plant, seeds intended for growing the plant, seedlings intended for growing the plant, or a plant locus. 15. A method for protecting a plant from attack by a fungus, wherein said method comprises applying a combination according to any one of claims 1-4 or a composition according to claim 5 or 6 to a plant, a locus of a plant or seeds or seedlings intended for growing the plant. 16. A method for controlling a fungal attack on a plant, comprising applying a combination according to any one of claims 1-4 or a composition according to claim 5 or 6 to the soil, plant, roots, leaves, seeds, locus of the fungus and/or the locus in which infection is to be prevented. 17. A method for combating fungal diseases of a plant and/or soil, comprising applying a combination according to any one of claims 1-4 or a composition according to claim 5 or 6 to the soil, plant, roots, leaves, seeds, fungal locus and/or locus in which infection must be prevented. 18. A method for treating a plant or plant locus, plant propagation material, plant seeds and/or seedlings, and/or soil against a fungal infection, comprising applying (i) an effective amount of a compound of formula I and (ii) an effective amount of a fungicide (A) selected from fluindapyr, wherein the weight ratio of the compound of formula I and the fungicide (A) is from 10:1 to 1:10, to thereby control the plant disease. 19. A method for treating a plant or a plant locus, plant propagation material, plant seeds and/or seedlings, and/or soil against a fungal infection according to paragraph 18, characterized in that - the compound of formula I and the fungicide (A) are used together or simultaneously, - the compound of formula I and the fungicide (A) are used separately or together, - the compound of formula I is used in an amount of 1 g/ha to 500 g/ha, and/or - fungicide (A) is used in quantities from 0.1 g/ha to 500 g/ha. 20. A method for treating a plant or a plant locus, plant propagation material, plant seeds and/or seedlings, and/or soil against a fungal infection according to claim 18 or 19, characterized in that the compound of formula I is used in an amount of 5 g/ha or 10 g/ha. 21. A method for treating a plant or plant locus, plant propagation material, plant seeds and/or seedlings, and/or soil against a fungal infection according to claim 18 or 19, characterized in that fluindapyr is used in an amount of from 0.1 g/ha to 150 g/ha. 22. A method for controlling a plant disease caused by phytopathological fungi, comprising contacting a plant, plant propagation material or plant locus with (i) an effective amount of a compound of formula I and (ii) an effective amount of a fungicide (A) selected from fluindapyr, wherein the weight ratio of the compound of formula I and the fungicide (A) is from 10:1 to 1:10 to thereby control a plant disease. 23. A method for controlling a fungal attack on a plant, seed or seedling comprising applying to the plant, seed, seedling and/or locus of the plant (i) an effective amount of a compound of formula I and (ii) an effective amount of a fungicide (A) selected from fluindapyr, wherein the weight ratio of the compound of formula I to the fungicide (A) is from 10:1 to 1:10 to thereby control the attack of the fungus on the plant, seeds or seedlings. 24. A method for protecting a plant, seed or seedling from attack by a fungus, comprising applying to the plant, seed, seedling and/or locus of the plant (i) an effective amount of a compound of formula I and (ii) an effective amount of a fungicide (A) selected from fluindapyr, wherein the weight ratio of the compound of formula I to the fungicide (A) is from 10:1 to 1:10 to thereby protect the plant, seed or seedling from attack by the fungus. 25. Use of a combination according to any one of claims 1 to 4 or a composition according to claim 5 or 6 for treating a plant or a locus of a plant against a fungal infection. 26. A combination according to any one of claims 1 to 4 or a composition according to claim 5 or 6 for use in treating a plant or a locus of a plant from a fungal infection.