Mixtures and compositions comprising 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2-one, and methods of using the same

Abstract

The present invention provides stable liquid compositions comprising (a) a bactericidal amount of a compound of Formula I and (b) a liquid carrier. The present invention also provides mixtures and compositions comprising (a) a bactericidal amount of a compound of Formula I and (b) at least one adjuvant selected from the group consisting of (i) a polyalkylene oxide alkyl ether, (ii) a siloxane polyalkylene oxide copolymer, (iii) an ester of a fatty acid, (iv) vinylpyrrolidone and its derivatives, and (v) a sugar surfactant. The present invention also provides methods of using the mixtures and compositions disclosed herein and methods of preparing the mixtures and compositions disclosed herein.

Description

Technical Field

[0001] This application claims the benefit of U.S. Provisional Patent Application No. 62 / 755,866, filed Nov. 5, 2018, the entire contents of which are incorporated herein by reference.

[0002] Throughout this application, various publications are referenced. The entire disclosures of these documents are incorporated herein by reference in order to more fully describe the state of the art to which this invention pertains.

Background Art

[0003] Background Fungicides are compounds of natural or synthetic origin that act to protect plants from damage caused by fungi. Current agricultural practices rely heavily on the use of fungicides. In fact, some crops cannot be grown profitably without the use of fungicides. The use of fungicides enables growers to increase yields and improve the quality of their crops, thereby increasing the value of the crops. In most situations, the increase in the value of the crops is worth at least three times the cost of using the fungicides.

[0004] 5-Fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1H)-one (compound of formula I) is a fungicide that provides control of various pathogens that adversely affect economically important crops, including but not limited to the wheat leaf blotch pathogen Zymoseptoria tritici (SEPTTR) and diseases caused by fungi of the Ascomycetes and Basidiomycetes classes.

[0005] The use of N3-substituted-N1-sulfonyl-5-fluoropyrimidinone derivatives as fungicides is described in U.S. Patent No. 8,263,603, issued on September 11, 2012, the entire content of which is incorporated herein by reference. The method for preparing 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1H)-one is described in U.S. Patent No. 9,850,215, issued on December 26, 2017, and U.S. Patent No. 9,840,476, issued on December 12, 2017, the entire contents of each of which are incorporated herein by reference.

[0006] U.S. Patent No. 8,263,603 also describes a fungicidal composition comprising an N3-substituted-N1-sulfonyl-5-fluoropyrimidinone derivative and a botanically acceptable carrier material for the control or prevention of fungal attack, as well as a method of using the same.

[0007] Fungicidal compositions are often applied under various conditions and / or in combination with other additives such as adjuvants and fertilizers. Therefore, fungicidal compositions must exhibit excellent chemical stability and a high level of physical stability during the preparation, storage, and application processes.

[0008] In agriculture, compositions are often diluted with water before use. Liquid compositions are much easier to dilute and disperse in water.

[0009] Currently, stable liquid compositions of 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1H)-one are not available in the art. Given the outstanding effectiveness of 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1H)-one in the control and / or prevention of fungal attack on plants, stable liquid compositions comprising 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1H)-one are highly needed in the art.

[0010] In some cases, the biological activity and effectiveness of a fungicide are limited for various reasons such as rapid drift, limited penetration into leaves, and high surface tension / low diffusion rate. The effectiveness of the active compound can be affected and enhanced by adding adjuvants.

[0011] An adjuvant is an inert chemical substance added to improve the performance of the active ingredient and its composition. Adjuvants affect the absorption state and delivery characteristics of the active ingredient, resulting in improved effectiveness and enhanced activity of the active ingredient. For example, adjuvants can enhance the effectiveness of the active ingredient, for example, by improving the properties of the spray solution to improve the deposition of the fungicide on the leaves.

[0012] The use of adjuvants suitable for the active ingredient and its composition often determines whether the active ingredient can be used and whether it can act with full effectiveness after spraying. Adjuvants are required to increase the reservoir of "available" substances for uptake on the leaf surface. Such adjuvants are often non-ionic surfactants or various types of oils.

[0013] U.S. Patent No. 8,263,603 discloses that a formulation containing an N3-substituted-N1-sulfonyl-5-fluoropyrimidinone derivative described therein may additionally contain an adjuvant surfactant to enhance the adhesion, wetting, and penetration of the compound to target crops and organisms. In improving U.S. Patent No. 8,263,603, the inventors of the present application have discovered that the selected adjuvant is particularly effective in enhancing the fungicidal effectiveness of 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1H)-one. SUMMARY OF THE INVENTION

[0014] Gist of the Invention The present invention relates to (a) a fungicidally effective amount of a compound of formula I:

[0015]

Chemical formula

[0016] In some embodiments, the solubility of the compound of Formula I in the liquid carrier is less than 5000 ppm. In some embodiments, the solubility of the compound of Formula I in the liquid carrier is less than 1000 ppm. In some embodiments, the composition comprises at least one stabilizing surfactant. In some embodiments, the pH value of the composition in the presence of water ranges from 5 to 7.5. In some embodiments, the composition has a water content of less than 0.5% by weight based on the total weight of the composition. In some embodiments, the composition has a viscosity of at least 500 cP (or in mPa·s units). In some embodiments, the composition has a viscosity of 500 cP to 3000 cP.

[0017] The present invention relates to (a) a bactericidally effective amount of a compound of Formula I:

[0018]

Chemical formula

[0019] The present invention is a method for controlling and / or preventing fungal pathogen attack on plants, comprising spraying any one of the compositions or mixtures described herein onto the soil, plant, roots, leaves, seeds, the location of the fungus, and / or the location where invasion is to be prevented, thereby controlling and / or preventing fungal pathogen attack on the plant.

[0020] The present invention is a method for controlling and / or preventing fungal diseases of plants and / or soil, comprising spraying any one of the compositions or mixtures described herein onto the soil, plant, roots, leaves, seeds, the location of the fungus, and / or the location where invasion is to be prevented, thereby controlling and / or preventing fungal diseases of the plant and / or soil.

[0021] The present invention is a method for controlling and / or preventing fungal pathogen attack on plants, comprising spraying a bactericidally effective amount of a compound having the formula (I):

[0022]

Chemical formula

[0023] The present invention is a method for controlling and / or preventing fungal diseases of plants and / or soil, comprising spraying a bactericidally effective amount of a compound having the formula (I):

[0024] [Chemical formula] A method of spraying a compound having [Chemical formula] and at least one adjuvant onto soil, plants, roots, leaves, seeds, fungal habitats, and / or locations where invasion is to be prevented, thereby controlling and / or preventing mycotic diseases of plants and / or soil, wherein the adjuvant is (i) polyalkylene oxide alkyl ether, (ii) siloxane polyalkylene oxide copolymer, (iii) ester of fatty acid, (iv) vinyl pyrrolidone and its derivatives, and (v) sugar-based surfactant selected from the group consisting of is also provided.

[0025] The present invention relates to a method for improving the biological activity of a compound of formula I against fungal pathogens, comprising spraying a compound of formula I:

[0026] [Chemical formula] in the presence of at least one adjuvant, thereby improving the biological activity of the compound of formula I, wherein the adjuvant is (i) polyalkylene oxide alkyl ether, (ii) siloxane polyalkylene oxide copolymer, (iii) ester of fatty acid, (iv) vinyl pyrrolidone and its derivatives, and (v) sugar-based surfactant selected from the group consisting of is provided.

[0027] The present invention relates to a compound of formula I:

[0028] [Chemical formula] A method for improving the stability of a liquid composition comprising a compound of formula I and a liquid carrier, the method comprising selecting the liquid carrier, wherein the solubility of the compound of formula I in the liquid carrier is less than 5000 ppm. In some embodiments, the solubility of the compound of formula I in the liquid carrier is less than 1000 ppm.

[0029] The present invention relates to formula I:

[0030]

Chemical formula

[0031] The present invention relates to formula I:

[0032]

Chemical formula

[0033] The present invention relates to formula I:

[0034]

Chemical formula

[0035] The present invention relates to formula I:

[0036]

Chemical formula

[0037] The present invention also provides a method for improving the stability of a non-aqueous liquid composition comprising a compound of formula I:

[0038]

Chemical formula

[0039] The present invention also provides a method for improving the stability of a liquid composition comprising a compound of formula I:

[0040]

Chemical formula

[0041] The present invention also provides the use of at least one stabilizing surfactant having the structure of a polyalkylene oxide polyaryl ether for controlling the solubility and / or degradation of a compound of formula I:

[0042]

Chemical formula

[0043] The present invention also provides a method for improving the stability of a liquid composition comprising a compound of formula I:

[0044]

Chemical formula

[0045] The present invention also provides a method for preparing a concentrated suspension (SC) composition disclosed herein, (1) Mixing an agriculturally acceptable inert additive and an aqueous liquid carrier to obtain a premix; (2) Adding a compound of formula I to the premix obtained in step (1) to obtain a mixture, and (3) Grinding the mixture obtained in step (2) to obtain the desired composition A method comprising is provided.

[0046] In some embodiments, the method includes adding an additional additive to the mixture of step (2) before grinding the mixture.

[0047] The present invention is a method for preparing a suspoemulsion (SE) composition disclosed herein, (1) Mixing an agriculturally acceptable inert additive and an aqueous liquid carrier to obtain a premix; (2) Adding a compound of formula I and at least one adjuvant to the premix obtained in step (1) to obtain a mixture, and (3) Grinding the mixture obtained in step (2) to obtain the desired composition A method comprising is provided.

[0048] The present invention is a method for preparing an oil dispersion (OD) composition disclosed herein, (1) Mixing an agriculturally acceptable inert additive and a non-aqueous liquid carrier to obtain a premix; (2) Adding a compound of formula I to the premix obtained in step (1) to obtain a mixture, and (3) Grinding the mixture obtained in step (2) to obtain the desired composition A method comprising is provided.

[0049] The present invention is a method for preparing an emulsifiable concentrate (EC) composition disclosed herein, (1) Mixing an agriculturally acceptable inert additive and a non-aqueous liquid carrier to obtain a premix; (2) Adding the compound of formula I to the premix obtained in step (1) to obtain a mixture, and (3) Filtering the solution of step (2) to obtain the desired composition A method comprising is provided. BRIEF DESCRIPTION OF THE DRAWINGS

[0050]

Figure 1

Figure 2

Figure 3

Figure 4

Figure 5

Figure 6

Figure 7

Figure 8

Figure 9

Figure 10

Mode for Carrying Out the Invention

[0051] Detailed Description of the Invention Definitions Unless otherwise defined, all technical and scientific terms used herein have the meaning commonly understood by one of ordinary skill in the art to which this subject pertains.

[0052] The terms "a" or "an" herein include the singular and plural forms unless otherwise specified. Thus, the terms "a", "an" or "at least one" can be used interchangeably in this application.

[0053] As used herein, the term "about", when used in connection with a numerical value, includes ±10% of the specified value. Additionally, all ranges for the same component or property in this specification include both endpoints and can be independently combined, including all intermediate points and ranges. When a parameter range is provided, all integers within that range and the first decimal place of those integers are also provided by the present invention. For example, "0.1 to 80%" includes 0.1%, 0.2%, 0.3%, etc. up to 80%.

[0054] As used herein, the term "plant" or "crop" includes reference to the whole plant, plant organs (e.g., leaves, stems, branches, roots, trunks, boughs, shoots, fruits, etc.), plant cells, or plant seeds. This term also encompasses the harvest of plants such as fruits. In yet another embodiment, the term "plant" may include reproductive parts such as seeds that can be used for plant propagation and its propagation materials such as cuttings and tubers that can be used for plant growth. This includes seeds, tubers, spores, bulbs, corms, rhizomes, basal shoots, stolons, and buds as well as other parts of the plant (including seedlings and young trees transplanted after germination or emergence from the soil).

[0055] As used herein, the term "location" includes not only the area where the infestation is controlled but also the area where the infestation is prevented and the area under cultivation.

[0056] As used herein, the term "mixture" or "combination" refers to any physical form of combination, such as blends, solutions, alloys, etc., without being limited thereto.

[0057] As used herein, the term "effective amount" refers to the amount of the compound sufficient to achieve a good control level when sprayed.

[0058] As used herein, the phrase "agriculturally acceptable" means that use in agricultural / pesticide applications is known and acceptable in the art.

[0059] As used herein, the term "adjuvant" is broadly defined as any substance that is not itself a fungicide but that enhances or is intended to enhance the effectiveness of a fungicide when used in combination with the adjuvant. Adjuvants can be understood to include, but are not limited to, spreading agents, penetrants, compatibilizers, and drift retardants. As used herein, the term "additive" is defined as any substance that is not itself a fungicide but that is added to a composition, such as a sticking agent, surfactant, synergist, buffering agent, acidifying agent, defoaming agent, and thickening agent.

[0060] As used herein, the term "built-in" means that all components, such as pesticides, adjuvants, and other additives, are included in the same composition.

[0061] As used herein, the term "tank mix" means mixing at least one pesticide and / or additive and / or adjuvant in a spray either before application or during injection spraying.

[0062] As used herein, the phrase "agriculturally acceptable carrier" means a carrier that is known and accepted in the art for the formation of compositions for agricultural or horticultural use.

[0063] As used herein, the term "thickening agent" refers to an auxiliary agent that increases the viscosity of a liquid composition without substantially changing other properties of the composition.

[0064] As used herein, the term "stability" refers to chemical stability, physical stability, or both.

[0065] As used herein, the term "stability," when used in connection with chemical stability, means that the composition meets the chemical stability criteria described by the United Nations Food and Agriculture Organization (FAO) in the Manual on Development and Use of FAO and WHO Specification for Pesticides (First Edition - Third Revision) (the "FAO / WHO Manual") (available at http: / / www.fao.org / agriculture / crops / thematic-sitemap / theme / pests / jmps / manual / en / ), the entire contents of which are incorporated herein by reference, if, for example, it is chemically stable. As described in the FAO / WHO Manual, the composition is stable if no significant decomposition of the active ingredient in the composition is observed after storage at a temperature of 54 ± 2 °C for 14 days, then at a temperature of 50 ± 2 °C for 4 weeks, then at a temperature of 45 ± 2 °C for 6 weeks, then at a temperature of 40 ± 2 °C for 8 weeks, then at a temperature of 35 ± 2 °C for 12 weeks, or then at a temperature of 30 ± 2 °C for 18 weeks. The amount of decomposition permitted before it is considered significant is determined by the concentration of the active ingredient in the composition. As described in the FAO / WHO Manual, in compositions containing from more than 25 to a maximum of 100 g / L of active ingredient, up to 10% decomposition of the active ingredient is considered non-significant decomposition; in compositions containing from more than 100 to a maximum of 250 g / L of active ingredient, up to 6% decomposition of the active ingredient is considered non-significant decomposition; in compositions containing from more than 250 to a maximum of 500 g / L of active ingredient, up to 5% decomposition of the active ingredient is considered non-significant decomposition; and in compositions containing more than 500 g / L of active ingredient, up to 25 g / L decomposition of the active ingredient is considered non-significant decomposition.

[0066] As used herein, the term "stability" when used in connection with physical stability, e.g., being physically stable, and when used in connection with a composition, means that the composition meets the physical stability criteria described by the Collaborative International Pesticides Analytical Council (CIPAC). CIPAC is an international organization that promotes international agreements on pesticide analytical methods and physicochemical test methods for formulations. The methods adopted by CIPAC are published in the CIPAC Handbooks available online at https: / / www.cipac.org / index.php / methods-publications, and the entire content of each method is incorporated herein by reference.

[0067] As used herein, the term "stabilizing surfactant" is defined as any surfactant that, when added to a liquid composition containing a compound of Formula I, improves the physical and / or chemical stability of the compound of Formula I. In some embodiments, the stabilizing surfactant is effective in suppressing crystal growth.

[0068] As used herein, the term "low water content" when used in connection with a surfactant or a carrier means that the surfactant or carrier can dissolve only an amount of water less than 25 g / L.

[0069] As used herein, the term "w / w" means weight percentage relative to the total weight of a composition or mixture.

[0070] As used herein, the term "liquid" means a liquid that is not a gas.

[0071] The compounds of formula I are pro-pesticide derivatives of N3-Me-5-FU containing a sensitive group such as a sulfonyl group and the imines at the N1 and C4 positions accordingly. These "groups" result in highly sensitive and unstable structures that require the development of specific conditions to stabilize the compounds of formula I in a liquid composition. In addition, the compounds of formula I have several crystal forms, form crystals that are difficult to utilize, and tend to affect the penetration rate to the target.

[0072] The formulation of a composition containing an active ingredient often requires the addition of agriculturally acceptable inert additives such as surfactants, dispersants, emulsifiers, wetting agents, defoamers, solvents, co-solvents, light stabilizers, ultraviolet absorbers, radical scavengers and antioxidants, adhesives, neutralizing agents, thickeners, binders, sequestering agents, biocides, buffers, preservatives, and antifreeze agents. The addition of additives affects the solubility of the active ingredient and results in a chemically and physically unstable composition.

[0073] The solvents and additives that can be used for the compounds of formula I should be neutral, that is, it is necessary that they do not contain active functional groups that can affect the stability of the compounds of formula I and cause decomposition. The solvents and / or additives used for formulating the compounds of formula I should be non-reactive with respect to the compounds of formula I.

[0074] The functional groups that can affect the stability of the compounds of formula I are groups containing N and / or O such as S-O, OH, and non-sterically hindered amides and amines. It has been found that the chemical stability of the compounds of formula I in amide solvents is determined by the substituents of the amide. The reactivity of the solvents and / or additives is important in formulating a stable composition containing the compounds of formula I. Reactive nucleophilic groups are groups such as hydroxyl groups with a bond dissociation energy of less than 120 Kcal / mol, weakly dissociating hydrogen bonds, or acidic functional groups.

[0075] The concentration of water in the composition is another important factor for chemical and / or physical stability.

[0076] For the reasons described above, the formulation of the compound of formula I in a liquid composition is particularly difficult.

[0077] It has been discovered that the stability of the compound of formula I in a liquid carrier can be improved by controlling the solubility of the compound of formula I in the liquid carrier, controlling the pH of the composition in an aqueous environment, controlling the water content of the composition, adding a surfactant effective to prevent crystal growth, and / or controlling the viscosity of the composition.

[0078] A stable liquid composition comprising a compound of formula I, as well as methods of using and preparing the same, are described below.

[0079] Stable liquid composition: The present invention provides (a) a bactericidally effective amount of a compound of formula I:

[0080]

Chemical formula

[0081] In some embodiments, the solubility of the compound of formula I in the liquid carrier is less than 5000 ppm. In some embodiments, the solubility of the compound of formula I in the liquid carrier is less than 1000 ppm. In some embodiments, the solubility of the compound of formula I in the liquid carrier is in the range of 50 - 500 ppm. In some embodiments, the solubility of the compound of formula I in the liquid carrier is about 200 ppm. In some embodiments, the solubility of the compound of formula I in the liquid carrier is about 80 ppm.

[0082] In some embodiments, the composition comprises at least one stabilizing surfactant. In some embodiments, the composition comprises at least two stabilizing surfactants. In some embodiments, the composition comprises two stabilizing surfactants. In some embodiments, the composition further comprises a stabilizing system.

[0083] In some embodiments, the composition comprises at least one anionic stabilizing surfactant. In some embodiments, the composition comprises at least one nonionic stabilizing surfactant. In some embodiments, the composition comprises two stabilizing surfactants. In some embodiments, the composition comprises a stabilizing system. In some embodiments, the composition comprises a combination of a nonionic stabilizing surfactant and an ionic stabilizing surfactant.

[0084] In some embodiments, the stabilizing surfactant affects the solubility of the compound of formula I in the liquid carrier.

[0085] In some embodiments, the pH of the composition ranges from 5 to 7.5. In some embodiments, the pH of the composition ranges from 6 to 7. In some embodiments, the pH of the composition is about 5. In some embodiments, the pH of the composition is about 5.5. In some embodiments, the pH of the composition is about 5.8. In some embodiments, the pH of the composition is about 6. In some embodiments, the pH of the composition is about 6.5. In some embodiments, the pH of the composition is about 7. In some embodiments, the pH of the composition is about 7.5.

[0086] In some embodiments, the pH of the composition is measured when the composition is in the presence of water. The water may be present in the composition as a liquid carrier. Also, the water may be present in the composition as a result of dilution or wetting.

[0087] In some embodiments, the pH of the composition is measured without further dilution and / or wetting. In some embodiments, the pH of the composition is measured after dilution and / or wetting.

[0088] In some embodiments, the liquid carrier is water and the pH of the composition is measured without further dilution and / or wetting. In some embodiments, the liquid carrier is a non-aqueous carrier and the pH of the composition is measured after dilution and / or wetting.

[0089] In some embodiments, the composition comprises a pH adjuster.

[0090] The chemical stability of the composition is affected by the pH of the composition.

[0091] When the liquid carrier is non-aqueous, the amount of water in the composition should be less than 0.5% by weight, preferably less than 0.2% by weight based on the total weight of the composition.

[0092] In some embodiments, the non-aqueous composition has a water content of less than 0.5% by weight based on the total weight of the composition. In some embodiments, the non-aqueous composition has a water content of less than 0.4% by weight based on the total weight of the composition. In some embodiments, the non-aqueous composition has a water content of less than 0.3% by weight based on the total weight of the composition. In some embodiments, the non-aqueous composition has a water content of less than 0.2% by weight based on the total weight of the composition. In some embodiments, the non-aqueous composition has a water content of less than 0.1% by weight based on the total weight of the composition.

[0093] An amount of water of less than 0.5% by weight, preferably less than 0.2% by weight based on the total weight of the composition, can be achieved by methods including, but not limited to, drying the components of the composition before adding them to the composition and / or reducing the water content of the components (both active and inactive components) in the composition. Also, the water content of the composition may be controlled by using low water content surfactants, low water content carriers, water scavengers and / or desiccants.

[0094] In some embodiments, the composition includes a low water content surfactant. In some embodiments, the composition includes a low water content carrier. In some embodiments, the composition includes at least one water scavenger. In some embodiments, the composition includes at least one desiccant. In some embodiments, the low water content surfactant, low water content carrier, water scavenger and / or desiccant are added to the composition after the composition has been dried.

[0095] In some embodiments, the water scavenger is selected from the group consisting of tetraethyl orthosilicate, Dynasylan® and combinations thereof. In some embodiments, Dynasylan® is Dynasylan® P. These water scavengers reduce the water content of the non-aqueous liquid composition to less than 0.5 wt% and improve the stability of the composition. These water scavengers reduce the water content of the OD composition to less than 0.5 wt% and improve the stability of the composition. These water scavengers reduce the water content of the EC composition to less than 0.5 wt% and improve the stability of the composition.

[0096] In some embodiments, the amount of the water scavenger in the composition is about 0.5 - 7.5 wt% based on the total weight of the composition.

[0097] In some embodiments, the composition has a viscosity of at least 500 cP. In some embodiments, the composition has a viscosity of 500 cP - 3000 cP. In some embodiments, the composition has a viscosity of 500 cP - 2500 cP. In some embodiments, the composition has a viscosity of 800 cP - 3000 cP. In some embodiments, the composition has a viscosity of 1600 cP - 2200 cP. In some embodiments, the composition has a viscosity of 3000 cP or less.

[0098] In some embodiments, the composition has a viscosity of about 500 cP - 1000 cP. In some embodiments, the composition has a viscosity of about 1000 cP - 1500 cP. In some embodiments, the composition has a viscosity of about 1500 cP - 2000 cP. In some embodiments, the composition has a viscosity of about 2000 cP - 2500 cP. In some embodiments, the composition has a viscosity of about 2500 cP - 3000 cP.

[0099] In some embodiments, the composition has a viscosity of about 500 cP, about 600 cP, about 700 cP, about 800 cP, about 900 cP, about 1000 cP, about 1100 cP, about 1200 cP, about 1300 cP, about 1400 cP, about 1500 cP, about 1600 cP, about 1700 cP, about 1800 cP, about 1900 cP, about 2000 cP, about 2100 cP, about 2200 cP, about 2300 cP, about 2400 cP, about 2500 cP, about 2600 cP, about 2700 cP, about 2800 cP, about 2900 cP, about 3000 cP.

[0100] In some embodiments, the liquid carrier is an aqueous liquid carrier. In some embodiments, the aqueous liquid carrier is water.

[0101] In some embodiments, the liquid carrier is a non-aqueous liquid carrier.

[0102] In some embodiments, the solubility of the compound of Formula I in the aqueous liquid carrier is less than 5000 ppm. In some embodiments, the solubility of the compound of Formula I in the non-aqueous carrier is less than 5000 ppm.

[0103] In some embodiments, the compound of Formula I is in the form of solid particles. In some embodiments, the solid particles of the compound of Formula I are suspended in the aqueous carrier. In some embodiments, the solid particles of the compound of Formula I are suspended in the non-aqueous carrier.

[0104] In some embodiments, the compound of Formula I dissolves in the non-aqueous carrier.

[0105] When the solid particles of the compound of Formula I are suspended in the aqueous carrier, the composition is a thick suspension (SC).

[0106] When the SC composition containing the aqueous carrier further contains a non-aqueous liquid component, the SC composition is a suspoemulsion (SE). When the solid particles of the compound of formula I are suspended in the aqueous carrier and the composition further contains a non-aqueous liquid component, the composition is a suspoemulsion (SE). The non-aqueous liquid component may be, but is not limited to, an adjuvant, a carrier for the adjuvant, and / or any additive. In some embodiments, the non-aqueous liquid component is an adjuvant. The SC composition is an SE composition when the SC composition further contains a non-aqueous liquid component in the aqueous carrier.

[0107] When the solid particles of the compound of formula I are suspended in a non-aqueous carrier, the composition is an oil dispersion (OD).

[0108] When the compound of formula I is dissolved in a non-aqueous carrier, the composition is an emulsion (EC).

[0109] In some embodiments, the stable liquid composition is a thick suspension (SC) composition. In some embodiments, the composition is a suspoemulsion (SE) composition. In some embodiments, the composition is an oil dispersion (OD) composition. In some embodiments, the composition is an emulsion (EC) composition.

[0110] In some embodiments, the stable liquid composition is a thick suspension (SC) composition containing at least one stabilizing surfactant. In some embodiments, the stable liquid composition is a thick suspension (SC) composition containing two stabilizing surfactants.

[0111] In some embodiments, the stable liquid composition is a suspoemulsion (SE) composition containing at least one stabilizing surfactant. In some embodiments, the stable liquid composition is a suspoemulsion (SE) composition containing two stabilizing surfactants.

[0112] In some embodiments, the stable liquid composition is a thick suspension (SC) composition having a pH in the range of 5 to 7.5.

[0113] In some embodiments, the stable liquid composition is a suspoemulsion (SE) composition having a pH in the range of 5 to 7.5.

[0114] In some embodiments, the stable liquid composition is an oil dispersion (OD) composition having a water content of less than 0.5 wt% based on the total weight of the composition.

[0115] In some embodiments, the stable liquid composition is an emulsion (EC) composition having a water content of less than 0.5 wt% based on the total weight of the composition.

[0116] In some embodiments, the composition comprises an aqueous carrier and the aqueous composition has a viscosity of at least 500 cP. In some embodiments, the composition comprises an aqueous carrier and the aqueous composition has a viscosity of 3000 cP or less.

[0117] In some embodiments, the stable liquid composition is a thick suspension (SC) composition and the SC composition has a viscosity of at least 500 cP. In some embodiments, the stable liquid composition is a thick suspension (SC) composition and the SC composition has a viscosity of 800 to 3000 cP. In some embodiments, the stable liquid composition is a thick suspension (SC) composition and the SC composition has a viscosity of 1600 cP to 2200 cP. In some embodiments, the stable liquid composition is a thick suspension (SC) composition and the SC composition has a viscosity of 3000 cP or less.

[0118] In some embodiments, the composition comprises a non-aqueous liquid carrier and the non-aqueous composition has a viscosity of at least 500 cP. In some embodiments, the composition comprises a non-aqueous liquid carrier and the non-aqueous composition has a viscosity of 3000 cP or less.

[0119] In some embodiments, the stable liquid composition is an oil dispersion (OD) composition, and the OD composition has a viscosity of at least 500 cP. In some embodiments, the stable liquid composition is an oil dispersion (OD) composition, and the OD composition has a viscosity of 500 cP to 2500 cP. In some embodiments, the stable liquid composition is an oil dispersion (OD) composition, and the OD composition has a viscosity of 2500 cP or less.

[0120] The viscosity may be measured using the International Organization for the Coordination of Pesticide Analytical Methods (CIPAC) MT 192 - viscosity of liquids by rotational viscometer, the entire content of which is incorporated herein by reference. When the viscosity is described in the application of interest, the viscosity is measured using CIPAC MT 192 using spindle 62 at 12 rpm or using spindle 63 at 12 rpm.

[0121] In some embodiments, the viscosity is measured using spindle 62 at 12 rpm. In some embodiments, the viscosity is measured using spindle 63 at 12 rpm. In some embodiments, when measured using CIPAC MT192 with spindle 62 at 12 rpm or spindle 63 at 12 rpm, the composition has a viscosity of at least 500 cP. In some embodiments, when measured using CIPAC MT192 with spindle 62 at 12 rpm or spindle 63 at 12 rpm, the composition has a viscosity in the range of 500 cP to 3000 cP. In some embodiments, when measured using CIPAC MT192 with spindle 62 at 12 rpm or spindle 63 at 12 rpm, the composition has a viscosity in the range of 500 cP to 2500 cP. In some embodiments, when measured using CIPAC MT192 with spindle 62 at 12 rpm or spindle 63 at 12 rpm, the composition has a viscosity in the range of 800 cP to 3000 cP. In some embodiments, when measured using CIPAC MT192 with spindle 62 at 12 rpm or spindle 63 at 12 rpm, the composition has a viscosity in the range of 1600 cP to 2200 cP. In some embodiments, when measured using CIPAC MT192 with spindle 62 at 12 rpm or spindle 63 at 12 rpm, the composition has a viscosity of 3000 cP or less.

[0122] In some embodiments, the total amount of the aqueous carrier in the composition ranges from about 30% to about 70% by weight based on the total weight of the composition. In some embodiments, the total amount of the aqueous carrier in the composition ranges from about 40% to about 60% by weight based on the total weight of the composition. In some embodiments, the total amount of the aqueous carrier in the composition ranges from about 40% to about 50% by weight based on the total weight of the composition.

[0123] In some embodiments, the total amount of the aqueous carrier in the SC composition ranges from about 30% to about 70% by weight based on the total weight of the composition. In some embodiments, the total amount of the aqueous carrier in the SC composition ranges from about 40% to about 60% by weight based on the total weight of the composition. In some embodiments, the total amount of the aqueous carrier in the SC composition ranges from about 40% to about 50% by weight based on the total weight of the composition.

[0124] In some embodiments, the total amount of the aqueous carrier in the SE composition ranges from about 30% to about 70% by weight based on the total weight of the composition. In some embodiments, the total amount of the aqueous carrier in the SE composition ranges from about 40% to about 60% by weight based on the total weight of the composition. In some embodiments, the total amount of the aqueous carrier in the SE composition ranges from about 40% to about 50% by weight based on the total weight of the composition.

[0125] In some embodiments, the total amount of the non-aqueous carrier in the composition ranges from about 30% to about 80% by weight based on the total weight of the composition. In some embodiments, the total amount of the non-aqueous carrier in the composition ranges from about 40% to about 70% by weight based on the total weight of the composition. In some embodiments, the total amount of the non-aqueous carrier in the composition is about 50% by weight based on the total weight of the composition.

[0126] In some embodiments, the total amount of the non-aqueous carrier in the OD composition ranges from about 30% to about 80% by weight based on the total weight of the composition. In some embodiments, the total amount of the non-aqueous carrier in the OD composition ranges from about 40% to about 70% by weight based on the total weight of the composition. In some embodiments, the total amount of the non-aqueous carrier in the OD composition is about 50% by weight based on the total weight of the composition.

[0127] In some embodiments, the total amount of the non-aqueous carrier in the EC composition ranges from about 30% to about 80% by weight based on the total weight of the composition. In some embodiments, the total amount of the non-aqueous carrier in the EC composition ranges from about 40% to about 70% by weight based on the total weight of the composition. In some embodiments, the total amount of the non-aqueous carrier in the EC composition ranges from about 40% to about 80% by weight based on the total weight of the composition. In some embodiments, the total amount of the non-aqueous carrier in the EC composition is about 80% by weight based on the total weight of the composition.

[0128] In some embodiments, the concentration of the compound of Formula I in the stability liquid composition is from 150 g / L to 750 g / L. In some embodiments, the concentration of the compound of Formula I in the stability liquid composition is from 300 g / L to 750 g / L. In some embodiments, the concentration of the compound of Formula I in the stability liquid composition is 450 g / L. In some embodiments, the concentration of the compound of Formula I in the stability liquid composition is 660 g / L.

[0129] In some embodiments, the concentration of the compound of Formula I in the composition is more than 5% by weight based on the total weight of the stability composition. In some embodiments, the concentration of the compound of Formula I in the composition is more than 10% by weight based on the total weight of the stability composition. In some embodiments, the concentration of the compound of Formula I in the composition is more than 25% by weight based on the total weight of the stability composition. In some embodiments, the concentration of the compound of Formula I in the composition is more than 50% by weight based on the total weight of the stability liquid composition.

[0130] In some embodiments, the concentration of the compound of Formula I in the SC composition is more than 25% by weight based on the total weight of the stability composition. In some embodiments, the concentration of the compound of Formula I in the SC composition is more than 50% by weight based on the total weight of the stability liquid composition.

[0131] In some embodiments, the concentration of the compound of Formula I in the SE composition is more than 25% by weight based on the total weight of the stability composition. In some embodiments, the concentration of the compound of Formula I in the SE composition is more than 50% by weight based on the total weight of the stability liquid composition.

[0132] In some embodiments, the concentration of the compound of Formula I in the OD composition is greater than 25% by weight based on the total weight of the stability composition. In some embodiments, the concentration of the compound of Formula I in the OD composition is greater than 50% by weight based on the total weight of the stability liquid composition.

[0133] In some embodiments, the concentration of the compound of Formula I in the EC composition is greater than 5% by weight based on the total weight of the stability liquid composition. In some embodiments, the concentration of the compound of Formula I in the EC composition is greater than 10% by weight based on the total weight of the stability liquid composition. In some embodiments, the concentration of the compound of Formula I in the EC composition is greater than 25% by weight based on the total weight of the stability liquid composition.

[0134] In some embodiments, the composition comprising the non-aqueous carrier does not contain phosphoric acid. In some embodiments, the composition does not contain 2% or 5% phosphoric acid. In some embodiments, the composition contains 2% by weight or less of phosphoric acid. In some embodiments, the composition contains 5% by weight or less of phosphoric acid.

[0135] In some embodiments, the composition comprising the non-aqueous carrier does not contain urea. In some embodiments, the composition does not contain 1% or 2% urea. In some embodiments, the composition contains 1% by weight or less of urea. In some embodiments, the composition contains 2% by weight or less of urea.

[0136] In some embodiments, the composition comprising the non-aqueous carrier does not contain propyl gallate.

[0137] In some embodiments, the composition comprising the non-aqueous carrier does not contain dimethyl sulfoxide (DMSO).

[0138] In some embodiments, the composition comprising the non-aqueous carrier does not contain morpholine.

[0139] In some embodiments, the composition comprising the non-aqueous carrier does not contain N-methylpyrrolidone.

[0140] The present invention (a) a bactericidally effective amount of a compound of Formula I:

[0141]

Chem.

[0142] The present invention relates to (a) A bactericidally effective amount of a compound of formula I:

[0143]

Chem.

[0144] The present invention relates to (a) A bactericidally effective amount of a compound of formula I:

[0145]

Chem.

[0146] The present invention relates to (a) A bactericidally effective amount of a compound of formula I:

[0147]

Chem.

[0148] In some embodiments, the non-aqueous liquid carrier is used as an adjuvant.

[0149] (i) A compound of formula I The compounds of formula I of the present invention refer to any solid forms including, but not limited to, amorphous, crystalline, solvates or hydrates.

[0150] The compounds of formula I include the crystalline forms of the compounds of formula I.

[0151] In some embodiments, the crystalline form is an anhydrous crystalline form. In some embodiments, the anhydrous crystalline form is a polymorph. In some embodiments, the anhydrous crystalline form is a pseudopolymorph.

[0152] The polymorphs of the compounds of formula I are described in PCT International Application Publication No. WO 2019 / 038583 (published on February 28, 2019), the entire contents of which are incorporated herein by reference.

[0153] In some embodiments, the crystalline form is a hydrate.

[0154] In some embodiments, the crystalline form is a solvate. In some embodiments, the solvate contains 1,4-dioxane. In some embodiments, the solvate contains tetrahydrofuran. In some embodiments, the solvate contains ethyl acetate.

[0155] In some embodiments, the crystalline polymorphic form (Form I) exhibits an X-ray powder diffraction pattern having characteristic peaks at 2θ angles of 9.08, 10.98, 14.05, 17.51, 18.75, 21.63, 23.33, 24.70, 24.83, 25.37, 26.51 and 29.23. In one embodiment, the powder X-ray diffraction pattern of Form I includes characteristic peaks at 2θ angles of 14.05, 17.51, 18.75, 21.63 and 26.51. In one embodiment, the powder X-ray diffraction pattern of Form I includes characteristic peaks at 2θ angles of 14.05, 17.51, 18.75 and 21.63.

[0156] In some embodiments, the crystalline polymorphic form (Form I) is characterized by decomposition starting at a temperature above 210 °C.

[0157] In some embodiments, the crystalline polymorphic form (Form I) exhibits a differential scanning calorimetry (DSC) thermogram characterized by a dominant endothermic peak having a peak temperature of about 160 °C, a dominant endothermic peak having a start temperature of about 159 °C, and a dominant endothermic peak having a melting enthalpy of about 110 J / g.

[0158] In one embodiment, the crystalline polymorphic form (Form II) exhibits an X-ray powder diffraction pattern having characteristic peaks at 2θ angles of 7.98, 9.20, 9.96, 11.88, 15.99, 18.49, 21.23, 22.33, 22.59, 26.73. In one embodiment, the powder X-ray diffraction pattern of Form II includes characteristic peaks at 2θ angles of 9.20, 9.96, 11.88, 22.33 and 22.59. In one embodiment, the powder X-ray diffraction pattern of Form II includes characteristic peaks at 2θ angles of 9.20, 11.88, 22.33 and 22.59.

[0159] In one embodiment, the crystalline polymorphic form (Form II) exhibits a TG-FTIR thermogram characterized by decomposition starting at a temperature above 210 °C.

[0160] In one embodiment, the crystalline polymorphic form (Form II) exhibits a differential scanning calorimetry (DSC) thermogram characterized by a dominant endothermic peak having a peak temperature of about 157 °C, a dominant endothermic peak having a start temperature of about 156 °C, and a dominant endothermic peak having a melting enthalpy of about 112 J / g.

[0161] In one embodiment, the crystalline hydrate form (hydrate) exhibits an X-ray powder diffraction pattern having characteristic peaks at 2θ angles of 5.34, 7.48, 10.68, 16.05, 21.79, 22.99, 23.19, 24.95, 26.95, 27.63. In one embodiment, the powder X-ray diffraction pattern of the hydrate includes characteristic peaks at 2θ angles of 5.34, 7.48, 10.68, 16.05 and 21.79. In one embodiment, the powder X-ray diffraction pattern of the hydrate includes characteristic peaks at 2θ angles of 5.34, 7.48, 10.68 and 16.05.

[0162] In one embodiment, the crystalline hydrate form (hydrate) exhibits a TG-FTIR thermogram characterized by decomposition starting at a temperature above 190 °C.

[0163] In one embodiment, the crystalline hydrate form (hydrate) exhibits a differential scanning calorimetry (DSC) thermogram characterized by a dominant endothermic peak having a peak temperature of about 139.5 °C, a dominant endothermic peak having a start temperature of about 139 °C, and a dominant endothermic peak having a melting enthalpy of about 115 J / g, where the DSC is measured in a sealed pan.

[0164] In one embodiment, the crystalline hydrate form (hydrate) exhibits a differential scanning calorimetry (DSC) thermogram characterized by a dominant endothermic peak having a peak temperature of about 160 °C, a dominant endothermic peak having a start temperature of about 159 °C, and a dominant endothermic peak having a melting enthalpy of about 98 J / g, where the DSC is measured in an open pan.

[0165] In one embodiment, the crystalline solvate form (Form S5) exhibits an X-ray powder diffraction pattern having characteristic peaks at 2θ angles of 5.42, 7.50, 10.06, 10.82, 12.80, 16.91, 21.55, 23.13, 24.83, 26.81, 27.77. In one embodiment, the powder X-ray diffraction pattern of Form S5 includes characteristic peaks at 2θ angles of 5.42, 7.50, 10.06, 10.82 and 16.91. In one embodiment, the powder X-ray diffraction pattern of Form S5 includes characteristic peaks at 2θ angles of 5.42, 7.50, 10.82 and 16.91.

[0166] In one embodiment, the crystalline solvate form (Form S5) exhibits a TG-FTIR thermogram characterized by decomposition starting at a temperature above 180°C.

[0167] In one embodiment, the crystalline solvate form (Form S8) exhibits an X-ray powder diffraction pattern as shown in FIG. 13, having characteristic peaks at 2θ angles of 4.7, 5.00, 5.38, 6.26, 9.66, 15.93, 21.05, 23.97, 24.69. In one embodiment, the powder X-ray diffraction pattern of Form S8 includes characteristic peaks at 2θ angles of 4.7, 5.00, 5.38, 6.26, 9.66 and 23.97. In one embodiment, the powder X-ray diffraction pattern of Form S8 includes characteristic peaks at 2θ angles of 4.7, 5.00, 9.66 and 23.97.

[0168] In one embodiment, the crystalline solvate form (Form S8) exhibits a TG-FTIR thermogram characterized by decomposition starting at a temperature above 180°C.

[0169] In one embodiment, the crystalline solvate form (Form S1) exhibits an X-ray powder diffraction pattern having characteristic peaks at 2θ angles of 5.34, 7.48, 10.10, 10.68, 12.90, 16.07, 21.83, 23.09, 24.91, and 26.93. In one embodiment, the powder X-ray diffraction pattern of Form S1 includes characteristic peaks at 2θ angles of 5.34, 7.48, and 10.68. In one embodiment, the powder X-ray diffraction pattern of Form S1 includes characteristic peaks at 2θ angles of 5.34, 7.48, 10.68, and 21.83. In one embodiment, the powder X-ray diffraction pattern of Form S1 includes characteristic peaks at 2θ angles of 5.34, 7.48, 10.68, 16.07, and 21.83.

[0170] In one embodiment, the crystalline solvate form (Form S1) exhibits a TG-FTIR thermogram characterized by decomposition starting at a temperature above 200 °C.

[0171] In some embodiments, the compound of Formula I is a mixture of crystalline forms of the compound of Formula I.

[0172] In some embodiments, the mixture is a mixture of one or more anhydrous crystalline forms.

[0173] In some embodiments, the mixture is a mixture of crystalline Form I and crystalline Form II. In some embodiments, the mixture is at least 25% crystalline Form I. In some embodiments, the mixture is at least 50% crystalline Form I. In some embodiments, the mixture is at least 75% crystalline Form I.

[0174] In some embodiments, the mixture is a mixture of crystalline Form I and a crystalline hydrate form. In some embodiments, the mixture is at least 25% crystalline Form I. In some embodiments, the mixture is at least 50% crystalline Form I. In some embodiments, the mixture is at least 75% crystalline Form I.

[0175] In some embodiments, the mixture is a mixture of crystalline form II and crystalline hydrate form. In some embodiments, the mixture is at least 25% crystalline form II. In some embodiments, the mixture is at least 50% crystalline form II. In some embodiments, the mixture is at least 75% crystalline form II.

[0176] (ii) Suitable stabilizing surfactant In some embodiments, the composition comprises at least one stabilizing surfactant. In some embodiments, the composition comprises at least two stabilizing surfactants. In some embodiments, the composition comprises a stabilizing system.

[0177] In some embodiments, the composition comprises a nonionic stabilizing surfactant. In some embodiments, the composition comprises an anionic stabilizing surfactant. In some embodiments, the composition comprises a combination of a nonionic stabilizing surfactant and an anionic stabilizing surfactant.

[0178] In some embodiments, the suspension concentrate (SC) composition comprises at least one stabilizing surfactant. In some embodiments, the suspension concentrate (SC) composition comprises at least two stabilizing surfactants. In some embodiments, the suspension concentrate (SC) composition comprises two stabilizing surfactants.

[0179] In some embodiments, the composition is a suspoemulsion (SE) composition. In some embodiments, the SE composition comprises at least one stabilizing surfactant. In some embodiments, the SE composition comprises at least two stabilizing surfactants. In some embodiments, the SE composition comprises two stabilizing surfactants.

[0180] In some embodiments, the stabilizing surfactant is a physical stabilizer.

[0181] In some embodiments, the stabilizing surfactant affects the crystal growth rate of the compound of Formula I in the liquid carrier. In some embodiments, the stabilizing surfactant reduces the crystal growth rate of the compound of Formula I in the liquid carrier. In some embodiments, the stabilizing surfactant has crystal growth inhibiting properties. In some embodiments, the stabilizing surfactant is a crystal growth inhibitor.

[0182] 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, esters of alkoxylated amines, esters of alkoxylated diethylethanolamine, polyalkylene oxide alcohol ethers, and alcohols.

[0183] In some embodiments, the polymer is a block polymer of a random polymer. In some embodiments, the polymer is a triblock polymer. In some embodiments, the triblock polymer is an ABA block polymer. In some embodiments, the polymer has a low HLB (hydrophile-lipophile balance) value, preferably an HLB value of 5. In some embodiments, the polymer is Atlox™ 4912 (manufactured and sold by Croda).

[0184] In some embodiments, the nonionic stabilizing surfactant is an ester of an alkoxylated amine. In some embodiments, the ester of the alkoxylated amine is Atlox™ 4915 (manufactured and sold by Croda). In some embodiments, the nonionic stabilizing surfactant is Atlox™ 4915 (manufactured and sold by Croda). In some embodiments, the nonionic stabilizing surfactant is an alkoxylated diethylethanolamine. In some embodiments, the nonionic stabilizing surfactant is diethylethanolamine monotrimellate. In some embodiments, the nonionic stabilizing surfactant is Altox™ 4915 (manufactured and sold by Croda).

[0185] In some embodiments, the polyalkylene oxide alcohol ether is a fatty alcohol ether and / or a non-fatty alcohol ether.

[0186] In some embodiments, the nonionic stabilizing surfactant is an alkoxylated fatty alcohol.

[0187] In some embodiments, the alkoxylated fatty alcohol is Genapol® X080 (manufactured and sold by Clariant), Genapol® X050 (manufactured and sold by Clariant), tridecyl alcohol polyglycol ether, Rhodasurf® LA30 (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).

[0188] In some embodiments, the alkoxylated fatty alcohol is Genapol® X080 (manufactured and sold by Clariant), Genapol® X050 (manufactured and sold by Clariant), tridecyl alcohol polyglycol ether, or Rhodasurf® LA30 (manufactured and sold by Solvay).

[0189] In some embodiments, the alkoxylated fatty alcohol is Atlas™ 5002L.

[0190] In some embodiments, the alcohol has a short carbon chain of C1 - C6. In some embodiments, the alcohol has a long carbon chain of C7 - C20.

[0191] In some embodiments, the nonionic stabilizing surfactant is a nonionic derivative of polyalkylene oxide polyaryl ether.

[0192] In some embodiments, one of the stabilizing surfactants is an ionic surfactant. In some embodiments, one of the stabilizing surfactants is an ionic stabilizing surfactant.

[0193] In some embodiments, the ionic stabilizing surfactant is selected from the group consisting of Aerosol® OT - SE or Aerosol® OT - 100 (manufactured and sold by Solvay), Rhodacal® 70 / B (manufactured and sold by Solvay), and combinations thereof.

[0194] In some embodiments, the ionic stabilizing surfactant is an anionic stabilizing surfactant. The anionic stabilizing surfactant refers to a compound having anionic groups such as phosphonates and sulfonates. An example of an ionic surfactant that can be used is sodium dioctyl sulfosuccinate manufactured and sold by Solvay as Aerosol® OT - SE.

[0195] In some embodiments, the anionic stabilizing surfactant is an anionic derivative of polyalkylene oxide polyaryl ether.

[0196] In some embodiments, the 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.

[0197] In some embodiments, a composition comprising a nonionic stabilizing surfactant and an anionic stabilizing surfactant is an SC composition. In some embodiments, a composition comprising a nonionic stabilizing surfactant and an anionic stabilizing surfactant is an SE composition.

[0198] In some embodiments, one of the stabilizing surfactants is a derivative of a polyalkylene oxide polyaryl ether. In some embodiments, the derivative of the polyalkylene oxide polyaryl ether is a nonionic derivative of the polyalkylene oxide polyaryl ether. In some embodiments, the derivative of the polyalkylene oxide polyaryl ether surfactant is an anionic derivative of the polyalkylene oxide polyaryl ether.

[0199] In some embodiments, the composition comprises at least two stabilizing surfactants. In some embodiments, the two stabilizing surfactants comprise two derivatives of a polyalkylene oxide polyaryl ether. In some embodiments, the two stabilizing surfactants comprise a nonionic derivative of a polyalkylene oxide polyaryl ether and an anionic derivative of a polyalkylene oxide polyaryl ether.

[0200] In some embodiments, the nonionic derivative of the polyalkylene oxide polyaryl ether is a compound having an aryl group substituted with at least two aromatic groups.

[0201] In some embodiments, the nonionic derivative of the polyalkylene oxide polyaryl ether has the following structure:

[0202]

Chemical formula

[0203] In some embodiments, the nonionic derivative of the polyalkylene oxide polyaryl ether has the following structure:

[0204] [Chemistry] has.

[0205] In some embodiments, the anionic derivative of the polyalkylene oxide polyaryl ether is a compound having an aryl group substituted with at least two aromatic groups.

[0206] In some embodiments, the anionic derivative of the polyalkylene oxide polyaryl ether contains an anionic group selected from phosphate (PO4), phosphonate (PO3), sulfonate (SO3), and sulfate (SO4). In some embodiments, the anionic group of the anionic derivative of the polyalkylene oxide polyaryl ether has an anionic group selected from phosphate (PO4), phosphonate (PO3), sulfonate (SO3), and sulfate (SO4).

[0207] In some embodiments, the polyalkylene oxide polyaryl ether contains a polyalkylene oxide group selected from the group consisting of polyethylene oxide groups, 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.

[0208] The polyalkylene oxide may include, but is 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.

[0209] In some embodiments, the polyalkylene oxide polyaryl ether is a polyalkylene oxide styrylphenyl ether. In some embodiments, the polyalkylene oxide polyaryl ether is a polyalkylene oxide benzylphenyl ether. In some embodiments, the polyalkylene oxide polyaryl ether is a polyalkylene oxide bisphenyl ether. In some embodiments, the polyalkylene oxide polyaryl ether is a polyalkylene oxide tristyrylphenyl ether. In some embodiments, the polyalkylene oxide polyaryl ether is a polyalkylene oxide distyrylphenyl ether. In some embodiments, the polyalkylene oxide distyrylphenyl ether is a polyoxyethylene distyrylphenyl ether.

[0210] In some embodiments, the polyalkylene oxide polyaryl ether is an anionic stabilizing surfactant. An anionic stabilizing surfactant refers to a compound having anionic groups such as phosphonates and sulfonates.

[0211] In some embodiments, the salt contains a cation. In some embodiments, the cation is selected from the group consisting of sodium, potassium, ammonium, calcium, magnesium, and combinations thereof.

[0212] In some embodiments, the anionic derivative of the polyalkylene oxide polyaryl ether has the following structure:

[0213]

Chemical formula

[0214] In some embodiments, the anionic derivative of the polyalkylene oxide polyaryl ether is tristyrylphenol ethoxylate phosphate ester.

[0215] In some embodiments, the polyalkylene oxide polyaryl ether is tristyrylphenol ethoxylate phosphate. Preferably, the tristyrylphenol ethoxylate phosphate is Soprophor® 3D33 manufactured and sold by Solvay.

[0216] In some embodiments, the polyalkylene oxide polyaryl ether is 2,4,6-tri-(1-phenylethyl)phenol polyglycol ether having 54 EO. Preferably, the 2,4,6-tri-(1-phenylethyl)phenol polyglycol ether having 54 EO is Emulsogen® TS540 manufactured and sold by Clariant.

[0217] In some embodiments, the polyalkylene oxide polyaryl ether is ethoxylated tristyrylphenol. Preferably, the ethoxylated tristyrylphenol is Soprophor® TS / 54 manufactured and sold by Solvay.

[0218] In some embodiments, the salt contains at least one cation selected from the group consisting of sodium, potassium, ammonium, calcium, magnesium, and combinations thereof.

[0219] The polyalkylene oxide polyaryl ether surfactant may include, but is not limited to, polyphenylethylphenol and tristyrylphenol.

[0220] The polyalkylene oxide polyaryl ether surfactant may include, but is not limited to, an uncapped surfactant, a backend-capped surfactant, or a combination thereof.

[0221] In some embodiments, the composition comprises a combination of stabilizing surfactants, and the combination of stabilizing surfactants comprises a mixture of a nonionic polyalkylene oxide polyaryl ether surfactant and an anionic polyalkylene oxide polyaryl ether surfactant. In some embodiments, the nonionic surfactant is tristyrylphenol ethoxylate. In some embodiments, the anionic surfactant is tristyrylphenol ethoxylate phosphate ether.

[0222] In some embodiments, the combination of stabilizing surfactants comprises tristyrylphenol ethoxylate and tristyrylphenol ethoxylate phosphate ether.

[0223] In some embodiments, the nonionic polyalkylene oxide polyaryl ether is a compound having an ether group substituted with at least two groups containing an aromatic ring.

[0224] 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 block copolymer of polyoxyethylene. In some embodiments, the polyalkylene oxide group is a block copolymer of polyoxypropylene.

[0225] The polyalkylene oxide may include, but is not limited to, polyethoxylated groups, polypropoxylated groups, polybutoxylated groups, and any combination thereof.

[0226] The polyalkylene oxide may include, but is not limited to, copolymers and homopolymers.

[0227] The copolymer may include, but is not limited to, random polymers and block polymers.

[0228] In some embodiments, the polyalkylene oxide polyaryl ether is a polyalkylene oxide tristyrylphenyl ether. In some embodiments, the polyalkylene oxide tristyrylphenyl ether is a polyoxyethylene tristyrylphenyl ether. In some embodiments, the polyalkylene oxide tristyrylphenyl ether is a polyoxyethylene polyoxypropylene tristyrylphenyl ether.

[0229] In some embodiments, the polyalkylene oxide polyaryl ether is a polyalkylene oxide distyrylphenyl ether. In some embodiments, the polyalkylene oxide distyrylphenyl ether is a polyoxyethylene distyrylphenyl ether.

[0230] In some embodiments, the nonionic derivative of the polyalkylene oxide polyaryl ether is a tristyrylphenol ethoxylate phosphate ester.

[0231] In some embodiments, the stabilizing surfactant is a derivative of tristyrylphenol polyethylene glycol ether.

[0232] In some embodiments, the stabilizing surfactant is an anionic derivative of tristyrylphenol polyethylene glycol ether.

[0233] In some embodiments, the stabilizing surfactant is a nonionic derivative of tristyrylphenol polyethylene glycol ether.

[0234] In some embodiments, the composition contains two stabilizing surfactants, and the two stabilizing surfactants are Soprophor® 3D33 and Soprophor® TS / 54 (TSP54).

[0235] In some embodiments, the composition comprises two stabilizing surfactants, both of which are derivatives of polyalkylene oxide polyaryl ethers. In some embodiments, the composition comprises two stabilizing surfactants, one stabilizing surfactant is a nonionic derivative of polyalkylene oxide polyaryl ether, and one stabilizing surfactant is an anionic derivative of polyalkylene oxide polyaryl ether.

[0236] In some embodiments, the composition comprises at least two stabilizing surfactants, at least one of which is a nonionic derivative of polyalkylene oxide polyaryl ether and at least one of which is an anionic derivative of polyalkylene oxide polyaryl ether.

[0237] In some embodiments, the SC composition comprises two stabilizing surfactants, which are Soprophor® 3D33 and Soprophor® TS / 54 (TSP54).

[0238] In some embodiments, the SC composition comprises two stabilizing surfactants, both of which are derivatives of polyalkylene oxide polyaryl ethers. In some embodiments, the composition comprises two stabilizing surfactants, one stabilizing surfactant is a nonionic derivative of polyalkylene oxide polyaryl ether, and one stabilizing surfactant is an anionic derivative of polyalkylene oxide polyaryl ether.

[0239] In some embodiments, the SC composition comprises at least two stabilizing surfactants, at least one of which is a nonionic derivative of polyalkylene oxide polyaryl ether and at least one of which is an anionic derivative of polyalkylene oxide polyaryl ether.

[0240] In some embodiments, the SE composition includes two stabilizing surfactants, and the two stabilizing surfactants are Soprophor® 3D33 and Soprophor® TS / 54 (TSP54).

[0241] In some embodiments, the SE composition includes two stabilizing surfactants, and both stabilizing surfactants are derivatives of polyalkylene oxide polyaryl ethers. In some embodiments, the composition includes two stabilizing surfactants, one stabilizing surfactant is a nonionic derivative of polyalkylene oxide polyaryl ether, and one stabilizing surfactant is an anionic derivative of polyalkylene oxide polyaryl ether.

[0242] In some embodiments, the SE composition includes at least two stabilizing surfactants, at least one stabilizing surfactant is a nonionic derivative of polyalkylene oxide polyaryl ether, and at least one stabilizing surfactant is an anionic derivative of polyalkylene oxide polyaryl ether.

[0243] In some embodiments, the stabilizing surfactant is Soprophor® 3D33.

[0244] In some embodiments, the stabilizing surfactant is tristyrylphenol ethoxylate phosphate ester.

[0245] In some embodiments, the polyalkylene oxide polyaryl ether is Soprophor® 3D33 manufactured by Solvay.

[0246] In some embodiments, the polyalkylene oxide polyaryl ether is Emulsogen® TS540 manufactured by Clariant.

[0247] In some embodiments, the polyalkylene oxide polyaryl ether is Soprophor® TS / 54 manufactured by Solvay.

[0248] In some embodiments, the salt containing a cation is selected from the group consisting of sodium, potassium, ammonium, calcium, magnesium, and combinations thereof.

[0249] Polyaryl may refer to, but is not limited to, polyphenylethylphenol and tristyrylphenol.

[0250] The polyalkylene oxide polyaryl ether surfactant refers to an uncapped surfactant, a backend-capped surfactant, or a combination thereof.

[0251] In some embodiments, the combination of surfactants includes a mixture of a nonionic polyalkylene oxide polyaryl ether surfactant and an anionic polyalkylene oxide polyaryl ether surfactant. In some embodiments, the nonionic surfactant is tristyrylphenol ethoxylate. In some embodiments, the anionic surfactant is tristyrylphenol ethoxylate phosphate ether.

[0252] In some embodiments, the combination of surfactants includes tristyrylphenol ethoxylate and tristyrylphenol ethoxylate phosphate ether.

[0253] In some embodiments, the nonionic polyalkylene oxide polyaryl ether is a compound having an ether group substituted with at least two groups containing an aromatic ring.

[0254] 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 block copolymer of polyoxyethylene. In some embodiments, the polyalkylene oxide group is a block copolymer of polyoxypropylene.

[0255] The polyalkylene oxide may include, but is not limited to, polyethoxylated groups, polypropoxylated groups, polybutoxylated groups, and any combination thereof.

[0256] The polyalkylene oxide may include, but is not limited to, copolymers and homopolymers.

[0257] The copolymer may include, but is not limited to, random polymers and block polymers.

[0258] In some embodiments, the polyalkylene oxide polyaryl ether is a polyalkylene oxide tristyrylphenyl ether. In some embodiments, the polyalkylene oxide tristyrylphenyl ether is a polyoxyethylene tristyrylphenyl ether. In some embodiments, the polyalkylene oxide tristyrylphenyl ether is a polyoxyethylene polyoxypropylene tristyrylphenyl ether.

[0259] In some embodiments, the polyalkylene oxide polyaryl ether is a polyalkylene oxide distyrylphenyl ether. In some embodiments, the polyalkylene oxide distyrylphenyl ether is a polyoxyethylene distyrylphenyl ether.

[0260] In some embodiments, the nonionic derivative of the polyalkylene oxide polyaryl ether is a tristyrylphenol ethoxylate phosphate ester.

[0261] In some embodiments, the stabilizing surfactant is Emulsogen® TS540.

[0262] In some embodiments, the nonionic derivative of the surfactant is Emulsogen® TS540.

[0263] In some embodiments, the stabilizing surfactant is Soprophor® TS / 54.

[0264] In some embodiments, the nonionic derivative of polyalkylene oxide polyaryl ether is Soprophor® TS / 54.

[0265] In some embodiments, the stabilizing surfactant is an anionic derivative of tristyrylphenol polyethylene glycol ether.

[0266] In some embodiments, the stabilizing surfactant is a nonionic derivative of tristyrylphenol polyethylene glycol ether.

[0267] In some embodiments, the composition includes a stabilizing system.

[0268] In some embodiments, the weight ratio of the nonionic derivative of polyalkylene oxide polyaryl ether to the anionic derivative of polyalkylene oxide polyaryl ether ranges from 0.25:1 to 1:1. In some embodiments, the weight ratio of the nonionic derivative of polyalkylene oxide polyaryl ether to the anionic derivative of polyalkylene oxide polyaryl ether ranges from 0.25:1 to 0.5:1. In some embodiments, the weight ratio of the nonionic derivative of polyalkylene oxide polyaryl ether to the anionic derivative of polyalkylene oxide polyaryl ether is about 0.36:1.

[0269] In some embodiments, the stability composition comprises at least 0.5 wt% of a polyalkylene oxide polyaryl ether stabilized surfactant based on the total weight of the composition. In some embodiments, the stability composition comprises from 0.5 wt% to 7 wt% of a polyalkylene oxide polyaryl ether stabilized surfactant based on the total weight of the composition. In some embodiments, the stability composition comprises from 0.5 wt% to 15 wt% of a polyalkylene oxide polyaryl ether stabilized surfactant based on the total weight of the composition. In some embodiments, the stability composition comprises from 0.5 wt% to 25 wt% of a polyalkylene oxide polyaryl ether stabilized surfactant based on the total weight of the composition.

[0270] In some embodiments, the weight ratio of the compound of Formula I to the nonionic derivative of polyalkylene oxide polyaryl ether is from 25:1 to 10:1. In some embodiments, the weight ratio of the compound of Formula I to the anionic derivative of polyalkylene oxide polyaryl ether is from 25:1 to 10:1.

[0271] In some embodiments, the stabilizing surfactant is effective to improve the stability of the compound of Formula I in the compositions described herein as compared to a liquid composition in which the compound of Formula I is soluble. In some embodiments, the stability is chemical stability. In some embodiments, the stability is physical stability.

[0272] (iii) Suitable pH adjuster In some embodiments, the composition comprises a pH adjuster.

[0273] In some embodiments, the pH adjuster may include, but is not limited to, buffers, bases, and / or acidifying agents.

[0274] In some embodiments, the pH adjuster is an acid. In some embodiments, the pH adjuster is a base.

[0275] In some embodiments, the pH adjuster is a mixture of at least one base and at least one acid.

[0276] In some embodiments, the pH adjuster is a buffer.

[0277] A buffer refers to a combination of an acid and a base. The acid includes, but is not limited to, organic acids and inorganic acids. The base includes, but is not limited to, organic bases and inorganic bases.

[0278] Examples of organic acids 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.

[0279] Examples of inorganic acids include, but are not limited to, hydrochloric acid, nitric acid, phosphoric acid, sulfuric acid, and boric acid.

[0280] Examples of organic bases include, but are not limited to, primary and secondary amines, pyridine, imidazole, and any combination thereof.

[0281] In some embodiments, the pH adjuster is potassium hydrogen phosphate.

[0282] In some embodiments, the pH adjuster is a combination of disodium hydrogen phosphate and potassium hydrogen phosphate.

[0283] In some embodiments, the stable liquid composition further comprises a buffer. In some embodiments, the amount of the buffer in the stable composition is 1 g / L to 20 g / L. In some embodiments, the stable liquid composition further comprises a buffer. In some embodiments, the amount of the buffer in the stable composition is 6 g / L to 15 g / L. In some embodiments, the stable liquid composition further comprises a buffer. In some embodiments, the amount of the buffer in the stable composition is 7 g / L to 10 g / L. In some embodiments, the concentration of the buffer in the stable composition is about 8.6 g / L.

[0284] In some embodiments, the buffer is potassium dihydrogen orthophosphate. In some embodiments, the concentration of potassium dihydrogen orthophosphate in the stability liquid composition is 1 g / L to 5 g / L. In some embodiments, the concentration of potassium dihydrogen orthophosphate in the stability liquid composition is 1 g / L to 3 g / L. In some embodiments, the concentration of potassium dihydrogen orthophosphate in the stability liquid composition is about 1.7 g / L.

[0285] In some embodiments, the buffer is disodium hydrogen phosphate anhydrous. In some embodiments, the concentration of disodium hydrogen phosphate anhydrous in the stability liquid composition is 1 g / L to 10 g / L. In some embodiments, the concentration of disodium hydrogen phosphate anhydrous in the stability liquid composition is 5 g / L to 10 g / L. In some embodiments, the concentration of disodium hydrogen phosphate anhydrous in the stability liquid composition is 5 g / L to 8 g / L. In some embodiments, the concentration of disodium hydrogen phosphate anhydrous in the stability liquid composition is about 6.9 g / L.

[0286] (iv) Suitable non-aqueous liquid carriers In some embodiments, the non-aqueous liquid carrier comprises one organic solvent.

[0287] In some embodiments, the non-aqueous liquid carrier comprises at least two organic solvents.

[0288] In some embodiments, the organic solvent is a non-aromatic solvent. In some embodiments, the non-aromatic solvent is an aprotic solvent.

[0289] In some embodiments, the organic solvent refers to a co-solvent.

[0290] The solubility of the compound of formula I in a solvent is determined by the polarity of the solvent. In some embodiments, the polarity of the solvent is 25 - 50 (when water is 100). Solvents (non-aqueous liquid carriers) may be combined when the combined polarity of the solvents is 25 - 50. In some embodiments, the solubility of water in the solvent is less than 25 g / L. In some embodiments, the solvent has a dipole (D) of less than 10, preferably less than 5, at 20 °C. In some embodiments, the solvent has a Log P value greater than 1.

[0291] In some embodiments, the non-aqueous carrier is selected from the group consisting of aromatic hydrocarbons, paraffins, petroleum, diesel, mineral oil, esters and / or amides of fatty acids, tall oil fatty acids, and any combination thereof.

[0292] In some embodiments, the non-aqueous carrier is an aromatic hydrocarbon.

[0293] In some embodiments, the aromatic hydrocarbon is selected from the group consisting of toluene, o-xylene, m-xylene, p-xylene, ethylbenzene, isopropylbenzene, tert-butylbenzene, naphthalene, and mono- or polyalkyl-substituted naphthalenes.

[0294] In some embodiments, the organic solvent is a paraffin.

[0295] In some embodiments, the non-aqueous liquid carrier is a vegetable oil. In some embodiments, the vegetable oil is selected from the group consisting of olive oil, kapok oil, castor oil, papaya oil, camellia oil, canola oil, palm oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil, linseed oil, tung oil, sunflower oil, safflower oil, and tall oil.

[0296] In some embodiments, the non-aqueous carrier is an ester of a fatty acid. In some embodiments, the alkyl ester of the fatty acid is C18 methyl canola oil ester. In some embodiments, the C18 methyl canola oil ester is Agnique® ME18RD-F (manufactured and sold by BASF).

[0297] In some embodiments, the non-aqueous carrier is an amide of a fatty acid. In some embodiments, the amide of the fatty acid is selected from the group consisting of C1-C3 amines, alkylamines and alkanolamines (having C6-C 18 carboxylic acid).

[0298] In some embodiments, the non-aqueous carrier is an alkyl ester of a fatty acid. In some embodiments, the alkyl ester of the fatty acid is selected from the group consisting of C8-C fatty acid C1-C4 monohydric alcohol esters such as methyl oleate and ethyl oleate. 22

[0299] Other examples of non-aqueous carriers are methyl fatty acid esters, vegetable oil alkyl esters, xylene, octanol, acetophenone, cyclohexanone, Solvesso® (manufactured and sold by ExxonMobil Chemical), N-methylpyrrolidone, tributyl sulfate (TBP), ethylhexyl lactate (EHL), alkyl (linear or cyclic) amides of fatty acids (natural or synthetic), aryl acetate (benzyl acetate), polyethylene carbonate, benzyl acetate, and propylene carbonate. In some embodiments, the non-aqueous carrier is cyclohexanone. In some embodiments, the non-aqueous carrier is acetophenone. In some embodiments, the non-aqueous carrier is benzyl acetate. In some embodiments, the non-aqueous carrier is propylene carbonate.

[0300] (v) Other additives The composition of the present invention may further comprise one or more additional agriculturally acceptable inert additives known in the art, including but not limited to solid diluents, liquid diluents, wetting agents, adhesives, thickeners, defoamers, preservatives, wetting agents, antioxidants, binders, fertilizers, or antifreeze agents. Additionally, the composition may further comprise additional crop protection agents known in the art, such as insecticides, safeners, agents for controlling phytopathogenic fungi or bacteria, etc.

[0301] In some embodiments, the liquid stable liquid composition further comprises a rheology modifier. The rheology modifier can be used to reduce phase separation, improve physical stability, and increase the viscosity that affects chemical stability.

[0302] In some embodiments, the rheology modifier is Bentone SD®-1 (modified bentonite) or Bentone SD®-3 (modified hectorite) (manufactured by Elementis). In some embodiments, the amount of Bentone SD®-1 or Bentone SD®-3 in the composition is between 0.5 and 1.0% by weight. In some embodiments, the rheology modifier is Attagel® 50 (manufactured by BASF) and Bentone SD®-1. In some embodiments, the amount of Attagel® 50 in the composition is 0.5% by weight, and the amount of Bentone SD®-1 in the composition is 0.5% by weight. The use of Attagel® 50 (0.5% by weight based on the total weight of the composition) and Bentone SD®-1 (0.5% by weight based on the total weight of the composition) reduced the decomposition of the compound of formula I from 7-8% to 4% after storage at 40 °C for 8 weeks. The water concentration of the composition should be maintained below 0.5%, including when Bentone SD®-1 is used as the rheology modifier.

[0303] In some embodiments, the rheology modifier is xanthan gum.

[0304] In some embodiments, the rheology modifier is a thickening agent.

[0305] In some embodiments, the thickening agent is a silica thickening agent.

[0306] In some embodiments, the thickening agent is selected from the group consisting of Aerosil® 200, Aerosil® R972, Aerosil® R202, and any combination thereof.

[0307] In some embodiments, the silica thickening agent is selected from the group consisting of Aerosil® R202, Aerosil® R812, and any combination thereof.

[0308] In some embodiments, the amount of Aerosil® R202 in the composition is between 1 wt% and 5 wt% based on the total weight of the composition. In some embodiments, the amount of Aerosil® R202 in the composition is between 1.7 wt% and 2.5 wt% based on the total weight of the composition.

[0309] In some embodiments, the amount of Aerosil® R812 in the composition is between 1 wt% and 5 wt% based on the total weight of the composition. In some embodiments, the amount of Aerosil® R812 in the composition is between 3.0 wt% and 3.5 wt% based on the total weight of the composition.

[0310] In some embodiments, the amount of Bentone SD®-1 or Bentone SD®-3 in the composition is between 0.5 and 1.0 wt% based on the total weight of the composition.

[0311] In some embodiments, the concentration of the rheology modifier in the stability liquid composition is from 1 g / L to 150 g / L. In some embodiments, the concentration of the rheology modifier in the stability liquid composition is from 1 g / L to 5 g / L. In some embodiments, the concentration of the rheology modifier in the stability liquid composition is 2.3 g / L. In some embodiments, the concentration of the rheology modifier in the stability liquid composition is from 0.5 g / L to 130 g / L. In some embodiments, the concentration of the rheology modifier in the stability liquid composition is 3 g / L.

[0312] In some embodiments, the composition further comprises at least one adjuvant. In some embodiments, the adjuvant is (i) a polyalkylene oxide alkyl ether, (ii) a siloxane polyalkylene oxide copolymer, (iii) an ester of a fatty acid, (iv) vinyl pyrrolidone and its derivatives, and (v) a sugar-based surfactant selected from the group consisting of.

[0313] Preferred adjuvants are described in more detail below.

[0314] In some embodiments, the composition of the present invention further comprises an additional acceptable inert additive. In some embodiments, the agriculturally acceptable inert additives include, but are not limited to, antioxidants, defoamers, dyes, pigments, flavoring agents, dispersants, synergists, encapsulants, light stabilizers, binders, stickers, water-soluble fertilizers, repellents and sensitizers.

[0315] In some embodiments, the method further comprises adding at least one dispersant.

[0316] In some embodiments, the stability liquid composition further comprises a dispersant. In some embodiments, the concentration of the dispersant in the stability liquid composition is from 1 g / L to 200 g / L.

[0317] In some embodiments, the stability liquid composition further comprises a wetting agent. In some embodiments, the wetting agent is sodium diisopropylnaphthalene sulfonate. In some embodiments, the concentration of the wetting agent in the stability composition is 1 g / L to 10 g / L. In some embodiments, the concentration of the wetting agent in the stability composition is 5.5 g / L.

[0318] In some embodiments, the stability liquid composition further comprises a thickening agent. In some embodiments, the thickening agent is xanthan gum. In some embodiments, the concentration of the thickening agent in the stability composition is 0.25 g / L to 10 g / L. In some embodiments, the concentration of the thickening agent in the stability composition is 2 g / L.

[0319] In some embodiments, the stability liquid composition further comprises an antifreeze. In some embodiments, the antifreeze is 1,2-propanediol. In some embodiments, the concentration of the antifreeze in the stability composition is 20 g / L to 70 g / L. In some embodiments, the concentration of the antifreeze in the composition is 57.5 g / L.

[0320] In some embodiments, the stability liquid composition further comprises an antifoaming agent. In some embodiments, the concentration of the antifoaming agent in the stability composition is 1 g / L to 5 g / L. In some embodiments, the concentration of the antifoaming agent in the composition is 2 g / L.

[0321] In some embodiments, the stability liquid composition further comprises an antioxidant. Examples of antioxidants include, but are not limited to, clay, BHA, BHT, TBH, propyl gallate, sodium thiosulfate, tocopherol, pyrogallol, and epichlorohydrin.

[0322] In some embodiments, the stability liquid composition further comprises a defoaming agent. Examples of defoaming agents include, but are not limited to, organosilicones, EO / PO defoaming agents, and alkyl polyacrylates.

[0323] In some embodiments, the stability liquid composition further comprises a dye. Examples of dyes include, but are not limited to, acid dyes, basic dyes, natural dyes, synthetic dyes, and azo dyes.

[0324] In some embodiments, the stability liquid composition further comprises a wetting agent. Examples of wetting agents include, but are not limited to, dialkyl naphthalenesulfonate, dialkyl sulfosuccinate, metal salts of alkyl ether sulfonic acid, alpha olefin sulfate ester, N-acyl N-alkyl taurate ester, linear alkylbenzene sulfonate ester, carboxylic acid ester, sulfate ester, phosphate ester, polyoxyethylene surfactant, ethoxylated alkylphenol, ethoxylated fatty alcohol, sorbitol anhydride ester, and cetyl trimethyl ammonium bromide.

[0325] In some embodiments, the stability liquid composition further comprises a surfactant.

[0326] Surfactants include, but are not limited to, alcohol polyglycol ethers, alkyl-capped ethoxylated glycols, alkyl-capped alkyl block alkoxylated glycols, dialkyl sulfosuccinates, phosphorylated esters, alkyl sulfonates, alkyl aryl sulfonates, tristyrylphenol alkoxylates, natural or synthetic fatty acid alkoxylates, natural or synthetic fatty alcohol alkoxylates, alkoxylated alcohols (such as n-butyl alcohol polyglycol ether), block copolymers (such as ethylene oxide-propylene oxide block copolymers and ethylene oxide-butylene oxide block copolymers), or combinations thereof.

[0327] In some embodiments, the surfactant is an alkyl end-capped alkoxylate. In some embodiments, the adjuvant is a methyl end-capped ethoxylate. In some embodiments, the adjuvant is a methyl end-capped tridecyl ethoxylate. In some embodiments, the adjuvant is a methyl end-capped tridecyl ethoxylate having six ethylene oxides.

[0328] In some embodiments, the surfactant is diisopropyl naphthalenesulfonate.

[0329] In some embodiments, the compositions disclosed herein may include additional pesticidal agents.

[0330] The disclosed compositions may optionally include at least 1 wt% of a combination of one or more of the compositions with another pesticidal compound. Such additional pesticidal compounds are compatible with the synergist compositions of the present disclosure in a medium selected according to the use, and may be fungicides, insecticides, nematicides, acaricides, arthropodicides, bactericides or combinations thereof that do not antagonize the action of the present compounds. Thus, in such embodiments, other pesticidal compounds of formula I are used as additional poisons when using the same or different pesticidal agents. The pesticidal compound and the synergist composition can generally be mixed at a weight ratio of 1:100 to 100:1.

[0331] A mixture comprising a compound of formula I and an adjuvant: An adjuvant is an inert chemical substance added to improve the performance of the active ingredient and its composition. Enhancing the activity of the compound of formula I is particularly difficult because it has a dramatic impact on penetration into plants, such as rapid drift and high surface tension of the droplets on the leaves, and many drawbacks that limit it are observed.

[0332] It has been discovered that spraying at least one selected adjuvant together with a compound of formula (I) enhances the efficacy of the compound of formula (I) in controlling fungal attack on plants. The selected adjuvant may be incorporated into a composition containing the compound of formula I. Also, the selected adjuvant may be added to a tank mix containing the compound of formula I. Additionally, when using multiple adjuvants, one or more adjuvants may be incorporated into the composition while adding other adjuvants to the tank mix.

[0333] The present invention relates to (a) a fungicidally effective amount of a compound of formula I:

[0334] [Chemical formula] and (b) (i) a polyalkylene oxide alkyl ether, (ii) a siloxane polyalkylene oxide copolymer, (iii) an ester of a fatty acid, (iv) vinyl pyrrolidone and its derivatives, and (v) a sugar-based surfactant and provides a fungicidal mixture comprising at least one adjuvant selected from the group consisting of .

[0335] In some embodiments, the fungicidal mixture is a composition. In some embodiments, the fungicidal mixture is a tank mix.

[0336] In some embodiments, the compound of Formula I is included in a composition. In some embodiments, the compound of Formula I is included in a stable liquid composition. The stable liquid composition of the compound of Formula I includes, but is not limited to, the stable liquid compositions disclosed herein. In some embodiments, the stable liquid composition is a concentrated suspension (SC) composition. In some embodiments, the stable liquid composition is a suspoemulsion (SE) composition. In some embodiments, the stable liquid composition is an oil dispersion (OD) composition. In some embodiments, the stable liquid composition is an emulsion (EC) composition.

[0337] In some embodiments, the polyalkylene oxide alkyl ether is a polyalkoxylated alcohol.

[0338] In some embodiments, the alkyl of the polyalkylene oxide alkyl ether includes, but is not limited to, a carbohydrate chain containing C1-C26.

[0339] In some embodiments, the alcohol of the polyalkoxylated alcohol includes, but is not limited to, a carbohydrate chain of C1-C26.

[0340] In some embodiments, the alkyl of the polyalkylene oxide alkyl ether includes, but is not limited to, short carbohydrate chains and long carbohydrate chains.

[0341] The carbohydrate chain can refer to, but is not limited to, a saturated chain, an unsaturated chain, a branched chain, and an unbranched chain.

[0342] In some embodiments, the short chain refers to C1-C8. In some embodiments, the long chain refers to C9-C26.

[0343] In some embodiments, the polyalkylene oxide refers to, but is not limited to, polyethylene oxide, polypropylene oxide, polybutylene oxide, or a combination thereof.

[0344] In some embodiments, the polyalkylene oxide includes, but is not limited to, copolymers. Copolymers refer to 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 diblock copolymer. In some embodiments, the polyalkylene oxide block copolymer is a triblock copolymer.

[0345] In some embodiments, the triblock copolymer is polyethylene oxide / polypropylene oxide / polyethylene oxide.

[0346] In some embodiments, the polyalkylene oxide alkyl ether is alkyl - terminated. In some embodiments, the alkyl includes, but is not limited to, short carbohydrate chains and long carbohydrate chains. Carbohydrate chains can refer to, but are not limited to, saturated chains, unsaturated chains, branched chains, and unbranched chains. In some embodiments, the short chain refers to C1 - C8.

[0347] In some embodiments, the polyalkylene oxide alkyl ether is isotridecyl alcohol polyglycol ether.

[0348] In some embodiments, the polyalkylene oxide alkyl ether is a C16 - C18 alcohol ethoxylate propoxylate ether.

[0349] In some embodiments, the C16 - C18 alcohol ethoxylate propoxylate ether is Ethylan™ 995 manufactured and sold by Akzo Nobel Agrochemicals. In some embodiments, the C16 - C18 alcohol ethoxylate propoxylate ether is Agnique® BP420 manufactured and sold by BASF.

[0350] In some embodiments, the polyalkylene oxide alkyl ether is an ethoxylated propoxylated alcohol.

[0351] In some embodiments, the ethoxylated propoxylated alcohol is Synperonic™ 13 / 9, manufactured and sold by Croda. In some embodiments, the ethoxylated propoxylated alcohol is Atplus™ PFA, manufactured and sold by Croda.

[0352] In some embodiments, the polyalkylene oxide alkyl ether is an isotridecyl alcohol polyglycol ether.

[0353] In some embodiments, the isotridecyl alcohol polyglycol ether is Genapol® X80, manufactured and sold by Clariant. In some embodiments, the isotridecyl alcohol polyglycol ether is Trycol®, manufactured and sold by BASF.

[0354] In some embodiments, the polyalkylene oxide alkyl ether is effective in reducing the surface tension of the composition and improving the spread of the compound of formula I on the leaves of plants. The reduction in surface tension leads to a reduction in drift from the leaves.

[0355] In some embodiments, the siloxane polyalkylene oxide copolymer refers to an organically modified trisiloxane.

[0356] In some embodiments, the siloxane polyalkylene oxide copolymer is Break-Thru® S233, manufactured by Evonik. In some embodiments, the siloxane polyalkylene oxide copolymer is Silwett® 077, manufactured by Momentive.

[0357] In some embodiments, the siloxane polyalkylene oxide copolymer is effective in reducing the surface tension of the composition. The silicone surfactant was found to be an effective aid in reducing surface tension and in the rapid spreading of the composition across the lipophilic surface.

[0358] In some embodiments, the esters of fatty acids may include, but are not limited to, alkyl esters of fatty acids and vegetable oils.

[0359] In some embodiments, the alkyl ester includes a carbohydrate chain containing C10 - C20.

[0360] In some embodiments, the alkyl includes, but is not limited to, a short carbohydrate chain.

[0361] The carbohydrate chain can refer to, but is not limited to, saturated chains, unsaturated chains, branched chains, and unbranched chains.

[0362] In some embodiments, the short chain refers to C1 - C8. In some embodiments, the fatty acid alkyl ester is Rhodaphac® PA / 23 (phosphoric acid ester of ethoxylated fatty alcohol) manufactured by Solvay or Alkamuls® VO / 2003 (ethoxylated (18EO) fatty acid) manufactured by Solvay.

[0363] In some embodiments, the adjuvant is ethoxylated tridecyl alcohol or polyoxyethylene (9) isotridecanol.

[0364] In some embodiments, the vegetable oil includes, but is not limited to, vegetable oil and its derivatives.

[0365] In some embodiments, the vegetable oil includes, but is not limited to, seed oil, coconut oil, rapeseed oil, castor oil, soybean oil, palm oil, and corn oil.

[0366] In some embodiments, derivatives of vegetable oils refer to alkyl esters and polyalkylene oxides.

[0367] Polyalkylene oxides refer to polyethylene oxide, polypropylene oxide, polybutylene oxide, and combinations thereof.

[0368] In some embodiments, vegetable oils and their derivatives include, but are not limited to, rapeseed oil methylated esters and coconut fatty acid esters of polyglycerol ethers.

[0369] In some embodiments, the adjuvant is a mixture of methylated seed oil and polyglycerol ester.

[0370] In some embodiments, the rapeseed oil methylated ester is Agnique® ME 18 RDF manufactured and sold by BASF.

[0371] In some embodiments, the polyalkylene oxide derivative of vegetable oil is a coconut fatty acid ester of polyglycerol ether.

[0372] In some embodiments, the coconut fatty acid ester of polyglycerol ether is Synergen® GL5 manufactured and sold by Clariant.

[0373] In some embodiments, the ester of fatty acid softens the leaf surface properties for better and more effective penetration of the compound of formula I.

[0374] In some embodiments, the derivative of vinyl pyrrolidone is a block copolymer of vinyl pyrrolidone and vinyl acetate (VP / VA).

[0375] In some embodiments, the block copolymer of vinyl pyrrolidone and vinyl acetate is Sokalan® VA64P manufactured and sold by Ashland.

[0376] In some embodiments, the block copolymer of vinyl pyrrolidone and vinyl acetate is Agrimer™ VA6, manufactured and sold by Ashland.

[0377] In some embodiments, vinyl pyrrolidone (PVP) and its derivatives are effective for enhancing the adhesion of the compound of Formula I to leaves for improving adhesion and retention properties (e.g., rain durability).

[0378] Saccharide-based surfactants may include, but are not limited to, sorbitan esters, sucrose esters, alkyl polyglycosides, and fatty acid glucamides.

[0379] In some embodiments, the saccharide-based surfactant is an alkyl or fatty acid glucamide derivative.

[0380] In some embodiments, the saccharide-based surfactant is an alkyl glucamide.

[0381] In some embodiments, the fatty acid glucamide is a C8 / C10 fatty acid glucose amide.

[0382] In some embodiments, the C8 / C10 fatty acid glucose amide is Synergen® GA manufactured by Clariant.

[0383] In some embodiments, the saccharide-based surfactant is sorbitan and its derivatives.

[0384] In some embodiments, the derivatives of sorbitan are polyethylene oxide derivatives and fatty acid esters.

[0385] In some embodiments, sorbitan is a di- or tri-fatty acid ester. In some embodiments, the derivative of sorbitan is a polyethylene oxide derivative containing 20 to 80 ethylene oxide groups.

[0386] In some embodiments, the derivative of sorbitan is Tween® 80.

[0387] In some embodiments, the sugar-based surfactant affects the leaf surface to improve the penetration of the compound of Formula I through the leaf surface.

[0388] In some embodiments, the bactericidal mixture includes a multi-adjuvant system. The multi-adjuvant system refers to a blend or any combination of adjuvants.

[0389] In some embodiments, the bactericidal mixture includes at least two adjuvants. In some embodiments, the bactericidal mixture includes at least three adjuvants.

[0390] In some embodiments, the adjuvants affect penetration in different ways. In some embodiments, the adjuvants affect penetration in the same way.

[0391] In some embodiments, the blend of adjuvants includes, but is not limited to, combinations with alkyl fatty acid esters and fatty alcohol alkoxylates.

[0392] In some embodiments, the combination of an alkyl fatty acid ester and a fatty alcohol alkoxylate is Synergen® SOC manufactured and sold by Clariant.

[0393] In some embodiments, the combination of an alkyl fatty acid ester and a fatty alcohol alkoxylate is FOP manufactured and sold by Clariant.

[0394] In some embodiments, the blend of adjuvants includes, but is not limited to, combinations with vegetable oils and / or their derivatives and sugar-based surfactants.

[0395] In some embodiments, the amount of compound (I) in the mixture is from 1 to 99.99% by weight.

[0396] In some embodiments, the amount of adjuvant in the mixture is from 0.01 to 95% by weight.

[0397] In some embodiments, the weight ratio range of the compound of formula I to the adjuvant is from 50:1 to 1:50. In some embodiments, the weight ratio range of the compound of formula I to the adjuvant is from 10:1 to 1:10. In some embodiments, the weight ratio range of the compound of formula I to the adjuvant is from 5:1 to 1:5. In some embodiments, the weight ratio of the compound of formula I to the adjuvant is 1:1.

[0398] In some embodiments, the volume ratio range of the compound of formula I to the adjuvant is from 50:1 to 1:50. In some embodiments, the volume ratio range of the compound of formula I to the adjuvant is from 10:1 to 1:10. In some embodiments, the volume ratio range of the compound of formula I to the adjuvant is from 5:1 to 1:5. In some embodiments, the volume ratio of the compound of formula I to the adjuvant is 1:1.

[0399] In some embodiments, the weight ratio of the compound of formula I to the adjuvant having the structure of vinylpyrrolidone and its derivatives is 25:1.

[0400] In some embodiments, the weight ratio of the compound of formula I to the adjuvant having a siloxane polyalkylene oxide copolymer structure is 50:1.

[0401] In one embodiment, the weight ratio of polyalkylene oxide alkyl ether to the compound of formula I in the mixture is 1:90.

[0402] In one embodiment, the weight ratio of vegetable oil and its derivatives to the compound of formula I in the mixture is 1:90.

[0403] In one embodiment, the weight ratio of vinylpyrrolidone and its derivatives to the compound of formula I in the mixture is 1:90.

[0404] In one embodiment, the weight ratio of the sugar-based surfactant to the compound of Formula I in the mixture is 1:90.

[0405] In some embodiments, the range of the weight ratio between two adjuvants is 5:1 to 1:5. In some embodiments, the weight ratio between two adjuvants is 2:1 to 1:2. In some embodiments, the weight ratio between two adjuvants is 1:1.

[0406] In some embodiments, the range of the weight ratio between an adjuvant having a vinyl pyrrolidone and its derivative structure and an adjuvant having a siloxane polyalkylene oxide copolymer structure is 5:1 to 1:5. In some embodiments, the weight ratio of the adjuvant having a vinyl pyrrolidone and its derivative structure to the adjuvant having a siloxane polyalkylene oxide copolymer structure is 2:1. In some embodiments, the weight ratio of the adjuvant having a vinyl pyrrolidone and its derivative structure to the adjuvant having a siloxane polyalkylene oxide copolymer structure is 1.4:1.

[0407] In some embodiments, the range of the weight ratio between an adjuvant having a vinyl pyrrolidone and its derivative structure and an adjuvant having a polyalkylene oxide alkyl ether structure is 10:1 to 1:10. In some embodiments, the weight ratio of the adjuvant having a vinyl pyrrolidone and its derivative structure to the adjuvant having a polyalkylene oxide alkyl ether structure is 1:5.5.

[0408] In some embodiments, the range of the weight ratio between an adjuvant having a vinyl pyrrolidone and its derivative structure and an adjuvant having a fatty acid ester structure is 5:1 to 1:5. In some embodiments, the weight ratio of the adjuvant having a vinyl pyrrolidone and its derivative structure to the adjuvant having a fatty acid ester structure is 1:3.7.

[0409] In some embodiments, the weight ratio range of the adjuvant having the structure of polyalkylene oxide alkyl ether to the adjuvant having the structure of fatty acid ester is 5:1 to 1:5. In some embodiments, the weight ratio range of the adjuvant having the structure of polyalkylene oxide alkyl ether to the adjuvant having the structure of fatty acid ester is 1.5:1.

[0410] In some embodiments, the weight ratio range of the adjuvant having the structure of polyalkylene oxide alkyl ether, the adjuvant having the structure of fatty acid ester, and the adjuvant having the structure of vinyl pyrrolidone and its derivatives is 10:5:1 to 1:5:10. In some embodiments, the weight ratio range of the adjuvant having the structure of polyalkylene oxide alkyl ether, the adjuvant having the structure of fatty acid ester, and the adjuvant having the structure of vinyl pyrrolidone and its derivatives is 5.7:3.76:1.

[0411] In some embodiments, the weight ratio range of two adjuvants in the multi - adjuvant system is 5:1 to 1:5 or 1:3 to 3:1 or 1:2 to 2:1 or 1:1.

[0412] In some embodiments, the weight ratio of the compound of formula I to the adjuvant is 5:1 to 1:5 or 1:3 to 3:1 or 1:2 to 2:1 or 1:1.

[0413] In some embodiments, the weight ratio of the compound of formula I to the adjuvant in the mixture is 5:1 to 1:5 or 1:3 to 3:1 or 1:2 to 2:1 or 1:1.

[0414] In some embodiments, the adjuvant is present in an amount of at least 0.1% by weight based on the total weight of the composition. In some embodiments, the adjuvant is present in an amount of at least 10% by weight based on the total weight of the composition. In some embodiments, the adjuvant is present in an amount of at least 15% by weight based on the total weight of the composition. In some embodiments, the adjuvant is present in an amount of at most 30% by weight based on the total weight of the composition.

[0415] In some embodiments, the mixture of the present invention formulated as a composition is referred to as a built-in composition. In some embodiments, the mixture is formulated into two separate compositions, and the compositions are added to the tank mix.

[0416] In some embodiments, the ratio of the adjuvant to compound (I) in the tank mix is from 50:1 to 1:50.

[0417] In some embodiments, the volume ratio range of the compound of formula I to the adjuvant is from 50:1 to 1:50. In some embodiments, the volume ratio range of the compound of formula I to the adjuvant is from 10:1 to 1:10. In some embodiments, the volume ratio range of the compound of formula I to the adjuvant is from 5:1 to 1:5. In some embodiments, the volume ratio of the compound of formula I to the adjuvant is 1:1.

[0418] In some embodiments, the concentration of the adjuvant having the structure of polyalkylene oxide alkyl ether in the composition / mixture is at least 3% by weight based on the total weight of the composition.

[0419] In some embodiments, the concentration of the adjuvant having the structure of siloxane polyalkylene oxide copolymer in the composition / mixture is at least 5% by weight based on the total weight of the composition.

[0420] In some embodiments, the concentration of the adjuvant having the structure of fatty acid ester in the composition / mixture is at least 3% by weight based on the total weight of the composition.

[0421] In some embodiments, the concentration of the adjuvant having the structure of vinyl pyrrolidone and its derivatives in the composition / mixture is from 0.1% by weight to 2.5% by weight based on the total weight of the composition.

[0422] In some embodiments, the concentration of the adjuvant having the structure of the sugar-based surfactant in the composition / mixture is at least 3% by weight based on the total weight of the composition.

[0423] In some embodiments, when the concentration of the polyalkylene oxide alkyl ether in the composition is less than 3% by weight based on the total weight of the composition, the polyalkylene oxide alkyl ether is used as a surfactant / emulsifier.

[0424] In this regard, when the concentration of the siloxane polyalkylene oxide copolymer in the composition is less than 5% by weight based on the total weight of the composition, the siloxane polyalkylene oxide copolymer is used as a surfactant / emulsifier.

[0425] In this regard, when the concentration of the fatty acid ester in the composition is less than 3% by weight based on the total weight of the composition, the fatty acid ester is used as a surfactant / emulsifier.

[0426] In this regard, when the concentration of the sugar-based surfactant in the composition is less than 3% by weight based on the total weight of the composition, the sugar-based surfactant is used as a surfactant / emulsifier.

[0427] In some embodiments, the composition of the compound (I) and / or the adjuvant is a liquid composition, a solid composition, or a combination thereof.

[0428] Examples of liquid compositions are concentrated suspension (SC) compositions, oil dispersion (OD) compositions, or emulsion (EC) compositions.

[0429] In one embodiment, the amount of the polyalkylene oxide alkyl ether in the mixture of the compound of formula I and the adjuvant or in the composition is in the range of about 1% to about 5% by weight based on the total weight of the composition.

[0430] In one embodiment, the amount of the siloxane polyalkylene oxide copolymer in the mixture of the compound of formula I and the adjuvant or in the composition ranges from about 1% to about 5% by weight based on the total weight of the composition.

[0431] In one embodiment, the amount of the fatty acid alkyl ester in the mixture of the compound of formula I and the adjuvant or in the composition ranges from about 1% to about 5% by weight based on the total weight of the composition.

[0432] In one embodiment, the amount of the vegetable oil and its derivatives in the mixture of the compound of formula I and the adjuvant or in the composition ranges from about 1% to about 5% by weight based on the total weight of the composition.

[0433] In one embodiment, the amount of vinyl pyrrolidone and its derivatives in the mixture of the compound of formula I and the adjuvant or in the composition ranges from about 1% to about 5% by weight based on the total weight of the composition.

[0434] In one embodiment, the amount of the sugar-based surfactant in the mixture of the compound of formula I and the adjuvant or in the composition ranges from about 1% to about 5% by weight based on the total weight of the composition.

[0435] In one embodiment, the amount of the polyalkylene oxide alkyl ether in the mixture of the compound of formula I and the adjuvant or in the composition ranges from about 1% to about 5% by weight based on the total weight of the composition.

[0436] In one embodiment, the amount of the siloxane polyalkylene oxide copolymer in the mixture of the compound of formula I and the adjuvant or in the composition ranges from about 1% to about 5% by weight based on the total weight of the composition.

[0437] In one embodiment, the amount of the fatty acid alkyl ester in the mixture of the compound of formula I and the adjuvant or in the composition ranges from about 1% to about 5% by weight based on the total weight of the composition.

[0438] In one embodiment, the amount of vegetable oil and its derivatives in the mixture of the compound of formula I and the adjuvant or in the composition ranges from about 1% to about 5% by weight based on the total weight of the composition.

[0439] In one embodiment, the amount of vinyl pyrrolidone and its derivatives in the mixture of the compound of formula I and the adjuvant or in the composition ranges from about 1% to about 5% by weight based on the total weight of the composition.

[0440] In one embodiment, the amount of sugar-based surfactant in the mixture of the compound of formula I and the adjuvant or in the composition ranges from about 1% to about 5% by weight based on the total weight of the composition.

[0441] In one embodiment, the concentration of polyalkylene oxide alkyl ether in the composition containing the compound of formula I is 5% by weight based on the total weight of the composition.

[0442] In one embodiment, the concentration of siloxane polyalkylene oxide copolymer in the composition containing the compound of formula I is 0.1% by weight based on the total weight of the composition.

[0443] In one embodiment, the concentration of fatty acid alkyl ester in the composition of the compound of formula I is 5% by weight based on the total weight of the composition.

[0444] In one embodiment, the concentration of vegetable oil and its derivatives in the composition containing the compound of formula I is 6% by weight based on the total weight of the composition.

[0445] In one embodiment, the concentration of vinyl pyrrolidone and its derivatives in the composition containing the compound of formula I is 1.5% by weight based on the total weight of the composition.

[0446] In one embodiment, the concentration of sugar-based surfactant in the composition containing the compound of formula I is 5% by weight based on the total weight of the composition.

[0447] In one embodiment, the amount of the polyalkylene oxide alkyl ether in the mixture of the compound of formula I and the adjuvant or in the composition is in the range of about 1% to about 5% by weight based on the total weight of the composition.

[0448] In one embodiment, the amount of the siloxane polyalkylene oxide copolymer in the mixture of the compound of formula I and the adjuvant or in the composition is in the range of about 1% to about 5% by weight based on the total weight of the composition.

[0449] In one embodiment, the amount of the fatty acid alkyl ester in the mixture of the compound of formula I and the adjuvant or in the composition is in the range of about 1% to about 5% by weight based on the total weight of the composition.

[0450] In one embodiment, the amount of the vegetable oil and its derivatives in the mixture of the compound of formula I and the adjuvant or in the composition is in the range of about 1% to about 5% by weight based on the total weight of the composition.

[0451] In one embodiment, the amount of the vinyl pyrrolidone and its derivatives in the mixture of the compound of formula I and the adjuvant or in the composition is in the range of about 1% to about 5% by weight based on the total weight of the composition.

[0452] In one embodiment, the amount of the sugar-based surfactant in the mixture of the compound of formula I and the adjuvant or in the composition is in the range of about 1% to about 5% by weight based on the total weight of the composition.

[0453] In some embodiments, the concentration of VP / VA in the composition is about 1 to 3% by weight based on the total weight of the composition. In some embodiments, the concentration of VP / VA in the composition is about 1.5% by weight based on the total weight of the composition.

[0454] In some embodiments, the concentration of PVP in the composition is about 0.5 to 1.5% by weight based on the total weight of the composition. In some embodiments, the concentration of PVP in the composition is about 0.75 to 1.25% by weight based on the total weight of the composition.

[0455] In some embodiments, the concentration of the siloxane polyalkylene oxide copolymer in the composition is about 0.25 to 2.5 wt% based on the total weight of the composition. In some embodiments, the concentration of VP / VA is about 0.1 to 2.0 wt% based on the total weight of the composition.

[0456] In some embodiments, the adjuvants in the multi - adjuvant system have similar properties.

[0457] In some embodiments, the adjuvants in the multi - adjuvant system have different properties.

[0458] In some embodiments, the adjuvant affects the surface properties of the leaf.

[0459] In some embodiments, the adjuvant affects the physical properties of the composition.

[0460] In some embodiments, a single adjuvant or a multi - adjuvant system / blend affects the surface tension of the droplet / composition / diluted composition, acts as an adherent, and improves the spread of the compound of formula I on the leaf.

[0461] In some embodiments, the penetration of the compound of formula I is increased by reducing the surface tension of the composition, thereby spreading the formulation on the leaf surface and enhancing the penetration.

[0462] In some embodiments, the adjuvant is also used as a solvent, surfactant, wetting agent, dispersant, and / or surfactant.

[0463] In some embodiments, the solvent, wetting agent, surfactant, dispersant, and / or surfactant of the composition is also used as an adjuvant.

[0464] In some embodiments, Agnique® ME 18 RD - F (fatty acids, C16 - 18 and C18 - unsaturated methyl esters) is a solvent and a built - in adjuvant.

[0465] In some embodiments, Genapol® x80 (isotridecyl alcohol polyglycol ether nonionic surfactant) is an emulsifier / surfactant and a built-in adjuvant.

[0466] In some embodiments, Agnique® ME 18 RD-F (fatty acids, C16 - 18 and C18-unsaturated methyl esters) is a solvent and a built-in adjuvant in the OD composition.

[0467] In some embodiments, Genapol® x80 (isotridecyl alcohol polyglycol ether nonionic surfactant) is an emulsifier / surfactant and a built-in adjuvant in the OD composition.

[0468] In some embodiments, the solvent Agnique® ME 18 RD-F (fatty acids, C16 - 18 and C18-unsaturated methyl esters) is also a built-in adjuvant.

[0469] In some embodiments, the emulsifier / surfactant Genapol® x80 (isotridecyl alcohol polyglycol ether nonionic surfactant) is also a built-in adjuvant.

[0470] In some embodiments, the solvent Agnique® ME 18 RD-F (fatty acids, C16 - 18 and C18-unsaturated methyl esters) is also a built-in adjuvant in the OD composition.

[0471] In some embodiments, the emulsifier / surfactant Genapol® x80 (isotridecyl alcohol polyglycol ether nonionic surfactant) is also a built-in adjuvant in the OD composition.

[0472] The composition is prepared according to conventional procedures in the field of pesticide technology, but is novel and important due to the presence of the mixture of the compound (I) of the present disclosure and the adjuvant.

[0473] The concentrated composition of the mixture of the present disclosure may be dispersed in water or another liquid depending on the use, or the composition may be in the form of dust or granules and can be applied without further treatment, or may be diluted before application.

[0474] In most cases, the composition applied is an aqueous suspension or emulsion. Such water-soluble, water-suspendable, or emulsifiable compositions are usually solids known as wettable powders, or liquids usually known as emulsions, aqueous suspensions, thick suspensions, or suspoemulsions. The present disclosure contemplates all vehicles for formulating the mixture for delivery and its use as a fungicide.

[0475] Additional pesticides: The mixtures and compositions of the present invention may further comprise one or more additional pesticides.

[0476] In some embodiments, the composition of the present invention further comprises at least one additional pesticidal agent. In some embodiments, the pesticidal agent is a fungicide, herbicide, insecticide, or nematicide.

[0477] In some embodiments, the composition of the present invention further comprises at least one additional fungicide. In some embodiments, the fungicidal mixture of the present invention further comprises at least one additional fungicide.

[0478] In some embodiments, at least one additional fungicide is a fungicidal sterol biosynthesis inhibitor.

[0479] In some embodiments, the sterol biosynthesis inhibitor is selected from the group consisting of prothioconazole, epoxiconazole, cyproconazole, myclobutanil, prochloraz, metconazole, difenoconazole, tebuconazole, tetraconazole, fenbuconazole, propiconazole, fluquinconazole, flusilazole, flutriafol, and fenpropimorph.

[0480] In some embodiments, the sterol biosynthesis inhibitor is selected from the group consisting of prothioconazole, epoxiconazole, metconazole, difenoconazole, propiconazole, prochloraz, tetraconazole, tebuconazole, fenpropimorph, fenpropidin, ipconazole, triticonazole, spiroxamine, fenhexamid, and fenpyrazamine.

[0481] 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 propiconazole. 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.

[0482] In some embodiments, the at least one additional fungicide is a succinate dehydrogenase inhibitor.

[0483] In some embodiments, the succinate dehydrogenase inhibitor is selected from the group consisting of benzovindiflupyr, penthiopyrad, isopyrazam, fluxapyroxad, boscalid, fluopyram, bixafen, and penflufen.

[0484] 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.

[0485] In some embodiments, at least one additional fungicide is a strobilurin fungicide.

[0486] In some embodiments, the strobilurin fungicide is selected from the group consisting of azoxystrobin, pyraclostrobin, picoxystrobin, fluoxastrobin, trifloxystrobin, kresoxim-methyl, dimoxystrobin, and orysastrobin.

[0487] In some embodiments, the strobilurin fungicide is selected from the group consisting of azoxystrobin, pyraclostrobin, picoxystrobin, fluoxastrobin, and trifloxystrobin.

[0488] In some embodiments, the strobilurin fungicide is azoxystrobin. 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 trifloxystrobin. 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.

[0489] In some embodiments, at least one additional bactericide is a bactericidal multi-site inhibitor.

[0490] In some embodiments, the bactericidal multi-site inhibitor is selected from the group consisting of mancozeb, chlorothalonil, folpet, captan, thiram, manneb, propineb, copper hydroxide, copper octanoate, copper oxychloride, copper sulfate, tribasic copper sulfate, mancopper, copper oxine, copper bis(3-phenylsalicylate), copper zinc chromate, cuprous oxide, copper sulfate hydrazinium, and cuprobam.

[0491] In some embodiments, the bactericidal multi-site inhibitor is mancozeb. In some embodiments, the bactericidal multi-site inhibitor is chlorothalonil. In some embodiments, the bactericidal multi-site inhibitor is folpet. In some embodiments, the bactericidal multi-site inhibitor is captan. In some embodiments, the bactericidal multi-site inhibitor is thiram. In some embodiments, the bactericidal multi-site inhibitor is manneb. In some embodiments, the bactericidal multi-site inhibitor is propineb. In some embodiments, the bactericidal multi-site inhibitor is copper hydroxide, copper octanoate, copper oxychloride, copper sulfate, tribasic copper sulfate, mancopper, copper oxine, copper bis(3-phenylsalicylate), copper zinc chromate, cuprous oxide, copper sulfate hydrazinium, or cuprobam.

[0492] In some embodiments, the additional fungicide is 2-(thiocyanatomethylthio)-benzothiazole, 2-phenylphenol, 8-hydroxyquinoline sulfate, amisulbrom, amisulpram, antimycin, Ampelomyces quisqualis, azaconazole, azoxystrobin, Bacillus subtilis, Bacillus subtilis strain QST713, benalaxyl, benomyl, benthiavalicarb-isopropyl, benzylaminobenzenesulfonic acid (BABS) salt, bicarbonate, biphenyl, bismerthiazol, bitertanol, bixafen, blasticidin S, borax, Bordeaux mixture, boscalid, bromoconazole, buthiopyram, calcium polysulfide, captan, captophos, carbendazim, carboxin, carpropamid, carvone, chlazafenone, chloroneb, chlorothalonil, chlorozolinate, Coniothyrium minitans, copper hydroxide, copper octanoate, copper oxychloride, copper sulfate, copper sulfate (tribasic), cuprous oxide, cyazofamid, cyflufenamid, cymoxanil, cyproconazole, cyprodinil, dazomet, debacarb, diammonium ethylenebis(dithiocarbamate), dichlofluanid, dichlorophen, dichlomezin, 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, epoxyconazole, ethaboxam, ethoxyquin, etridiazole, famoxadone, fenamidone, fenarimol, fenbuconazole, fenfluram, fenhexamid, phenoxanil, fenpiclonil, fenpropidin, fenpropimorph, fenpyrazamine, fenbutatin oxide, triphenyltin acetate, triphenyltin hydroxide, ferbam, ferimzone, fluazinam, fluazinam, fluopicolide, fluopyram, fluoroimide, fluoxastrobin, flucinoconazole, flusilazole, flusulfamide, flutianil,Flutolanil, Flutriafol, Fluquinconazole, Folpet, Formaldehyde, Hymexazol, Hymexazol - Aluminum, Fuberidazole, Fluralaxyl, Flametopyril, Guazatine, Guazatine Acetate, GY - 81, Hexachlorobenzene, Hexaconazole, Himexazol, Imazalil, Imazalil Sulfate, Imibenconazole, Iminoctadine, Iminoctadine Triacetate, Iminoctadine Albesilate, Iodocarb, Iproconazole, Ipflufenpyrrolone, Iprobenfos, Iprodione, Iprovalicarb, Isoprothiolane, Isopyrazam, Isothianil, Kasugamycin, Kasugamycin Hydrochloride Monohydrate, Cresoxime - Methyl, Laminarin, Mancozeb, Mandipropamid, Maneb, Mefenoxam, Mepanipyrim, Mepronil, Mephtyl - Dinocap, Mercuric Chloride, Mercuric Oxide, Mercurous Chloride, Metalaxyl, Metalaxyl - M, Metam, Metam Ammonium, Metam Potassium, Metam Sodium, Metconazole, Methiocarb, Methyl Iodide, Methyl Isothiocyanate, Methyram, Metominostrobin, Metrafenone, Milbemycin, Microbutanil, Nabam, Nitrothal - Isopropyl, Nuarimol, Octhilinone, Ofurace, Oleic Acid (Fatty Acid), Orysastrobin, Oxadixyl, Copper Oxinate, Oxpoconazole Fumarate, Oxolinic Acid, Pefurazoate, Penconazole, Pencycuron, Penflufen, Pentachlorophenol, Pentachlorophenyl Laurate, Penthiopyrad, Phenylmercury Acetate, Phosphonic Acid, Phthalide, Picoxystrobin, Polyoxin B, Polyoxin, Polyoxorim, Potassium Bicarbonate, Potassium Hydroxyquinoline Sulfate, Probenazole, Prochloraz, Procymidone, Propamocarb, Propamocarb Hydrochloride, Propiconazole, Propineb, Proquinazid, Prothioconazole, Pyraclostrobin, Pyrametostrobin, Pyraoxystrobin, Pyrazophos, Pyrisencarb, Pyributicarb, Pyriofenox, Pyrimethanil, Pyriofenone, Pyroquilone, Quinoclamine, Quinoxyfen, Quintozene, Reynoutria sachalinensis extract, Sedaxane, Silthiopham,Imazalil, sodium 2-phenylphenoxide, sodium bicarbonate, sodium pentachlorophenoxide, spiroxamine, sulfur, SYP-Z048, tall oil, tebuconazole, tebufloquin, tecnazen, tetraconazole, thiabendazole, chlorothalonil, thiophanate-methyl, thiram, thiazinyl, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triazoxide, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole, validamycin, valifenalate, valifenal, vinclozolin, dinneb, ziram, zoxamide, Candida oleophila, Fusarium oxysporum, Gliocladium spp., Phlebiopsis gigantea, Streptomyces griseoviridis, Trichoderma spp., (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-tetraoxide, 2-methoxyethyl mercury acetate, 2-methoxyethyl mercury chloride, 2-methoxyethyl mercury silicate, 3-(4-chlorophenyl)-5-methyl rhodanine, 4-(2-nitroprop-1-enyl) phenyl thiocyanate, ampropylfos, anilazine, azithiram, barium polysulfide, Bayer32394, benodanil, benquinox, bentazone, benzamacril, benzamacril-isobutyl, benzamorph, binapacryl, bis(methyl mercury) sulfate, bis(tributyltin) oxide, buthiobate,Selected from the group consisting of cadmium calcium copper zinc chromate sulfate, carbamorph, CECA, clobenilazone, chloraniformethane, chlorfenazole, chlorquinox, clinbazone, copper bis(3-phenylsalicylate), copper zinc chromate, cupraneb, copper hydrazinium sulfate, cuprobam, cyclafuramid, cypendazole, cyproflam, decafentin, diclone, diclomezine, diclobutrazol, dimethirimol, dinocap, dinosulfon, dinoterbon, dipyrithione, ditrimfos, dodine, drazoxolon, EBP, ESBP, etaconazole, etem, ethylrim, fenaminosulf, fenapanil, fenitrothion, fluotrimazole, flucarbanyl, fluconazole, fluconazole-cis, flumecyclox, folpet, glyodine, gliocladin, halacrine, Hercules3944, hexylthiofos, ICIA0858, isopamfos, isobavachin, mebenil, mecarbinzid, metazoxolon, metofluthrin, methylmercury dicyandiamide, methoxysulfobac, myclobutanil, mucobutolinic anhydride, microclozole, N-3,5-dichlorophenyl succinimide, N-3-nitrophenyl itaconimide, natamycin, N-ethylmercury-4-toluenesulfonanilide, nickel bis(dimethyldithiocarbamate), OCH, phenylmercury dimethyldithiocarbamate, phenylmercury nitrate, fosdiphen, prothiocarb, prothiocarb hydrochloride, pyracarbolid, pyridinonitrile, pyroxychlor, pyroxiflu, quinacetol, quinacetol sulfate, quinazamide, quinconazole, rabenzazole, salicylanilide, SSF-109, sultropen, tecloftalam, thiazifluron, thiochlorfenphim, thiophanate, thioquinox, thioximide, triamiphos, triarimol, triazbutyl, triclamide, urbacide, zarilamide, and any combination thereof.,

[0493] Synergist compositions comprising a compound of formula I and their use are described in U.S. Patent Nos. 9,526,245 (issued December 27, 2016), 10,045,533 (issued August 14, 2018), 9,532,570 (issued January 3, 2017), 10,045,534 (issued August 14, 2018), 9,538,753 (issued January 10, 2017), and 10,051,862 (issued August 21, 2018), the entire contents of each of which are incorporated herein by reference.

[0494] In some embodiments, the compositions of the invention further comprise at least one plant health stimulant. In some embodiments, the fungicidal mixtures of the invention further comprise at least one plant health stimulant.

[0495] In some embodiments, the plant health stimulant is selected from the group consisting of organic compounds, inorganic fertilizers or micronutrient donors, biocontrol agents, and inoculants.

[0496] Use and applications of the compositions described herein: The present invention also provides a method for controlling and / or preventing fungal pathogen attack on plants, comprising applying any one of the compositions or mixtures described herein to the soil, plant, roots, leaves, seeds, fungal habitats, and / or the location where invasion is to be prevented, thereby controlling and / or preventing fungal pathogen attack on the plants.

[0497] The present invention also provides any one of the compositions or mixtures described herein for use in controlling and / or preventing fungal attack on plants.

[0498] The present invention also provides the use of any one of the compositions or mixtures described herein for controlling and / or preventing fungal attack on plants.

[0499] The present invention also provides a method for controlling and / or preventing fungal diseases of plants and / or soil, comprising spraying any one of the compositions or mixtures described herein onto the soil, plants, roots, leaves, seeds, fungal habitats, and / or the location where invasion is to be prevented, thereby controlling and / or preventing fungal diseases of plants and / or soil.

[0500] The present invention also provides any one of the compositions or mixtures described herein for use in controlling and / or preventing fungal diseases of plants and / or soil.

[0501] The present invention also provides the use of any one of the compositions or mixtures described herein for controlling and / or preventing fungal diseases of plants and / or soil.

[0502] In some embodiments, the composition or mixture is sprayed onto a part of the plant, the area adjacent to the plant, the soil in contact with the plant, the soil adjacent to the plant, any surface adjacent to the plant, any surface in contact with the plant, the seeds, and / or the equipment used in agriculture.

[0503] In some embodiments, the composition or mixture is sprayed in an amount in the range of 5 g / ha to 150 g / ha of the compound of formula I. In some embodiments, the composition or mixture is sprayed in an amount of 6.25 g / ha of the compound of formula I. In some embodiments, the composition or mixture is sprayed in an amount of 10 g / ha of the compound of formula I. In some embodiments, the composition or mixture is sprayed in an amount of 12.5 g / ha of the compound of formula I. In some embodiments, the composition or mixture is sprayed in an amount of 20 g / ha of the compound of formula I. In some embodiments, the composition or mixture is sprayed in an amount of 75 g / ha of the compound of formula I. In some embodiments, the composition or mixture is sprayed in an amount of 100 g / ha of the compound of formula I. In some embodiments, the composition or mixture is sprayed in an amount of 125 g / ha of the compound of formula I.

[0504] In some embodiments, the composition or mixture is applied at seeding.

[0505] In some embodiments, the composition or mixture is applied 1 to 60 days after seeding.

[0506] In some embodiments, the composition or mixture is applied 1 to 9 months after seeding.

[0507] In some embodiments, the composition or mixture is applied once during the growth period.

[0508] In some embodiments, the composition or mixture is applied at least once during the growth period.

[0509] In some embodiments, the composition or mixture is applied two or more times during the growth period.

[0510] In some embodiments, the composition or mixture is applied as a foliage or seed treatment and / or soil application.

[0511] The present invention also provides a method for controlling and / or preventing fungal pathogen attack on a plant, comprising applying a fungicidally effective amount of a compound of formula (I):

[0512]

Chemical formula

[0513] The present invention also relates to a method for controlling and / or preventing mycotic diseases of plants and / or soil, comprising applying a fungicidally effective amount of a compound of formula (I):

[0514]

Chemical formula

[0515] The present invention relates to a method for improving the biological activity of a compound of formula I against fungal pathogens, the method comprising applying a compound of formula I:

[0516]

Chemical formula

[0517] In some embodiments, the compound of formula I is sprayed in the presence of at least two adjuvants.

[0518] The present invention also relates to (a) controlling and / or preventing fungal pathogen attack on plants and / or (b) controlling and / or preventing fungal diseases of plants and / or soil, Formula (I):

[0519]

Chemical formula

[0520] The present invention also relates to (a) controlling and / or preventing fungal pathogen attack on plants and / or (b) controlling and / or preventing fungal diseases of plants and / or soil for use in Formula (I):

[0521]

Chemical formula

[0522] The present invention relates to, for improving the biological activity of a compound of formula (I):

[0523]

Chemical formula

[0524] The present invention relates to, for use in improving the biological activity of a compound of formula (I):

[0525]

Chemical formula

[0526] Preferred adjuvants are described hereinabove.

[0527] In some embodiments, the compound of formula I and the adjuvant are sprayed simultaneously. In some embodiments, the compound of formula I and the adjuvant are sprayed sequentially.

[0528] In some embodiments, the compound of formula I and the adjuvant are applied separately. In some embodiments, the compound of formula I and the adjuvant are applied together. In some embodiments, the compound of formula I and the adjuvant are applied together as a tank mix. In some embodiments, the compound of formula I and the adjuvant are formulated as a single composition. In some embodiments, the adjuvant formulated together with the compound of formula I in the composition is a built-in adjuvant. An adjuvant that is tank mixed with the compound of formula I or applied separately, for example by spraying separately, is an add-on adjuvant.

[0529] In some embodiments, two or more adjuvants are applied, at least one adjuvant is a built-in adjuvant, and at least one adjuvant is an add-on adjuvant.

[0530] In some embodiments, the compound of formula I is applied in an amount in the range of 5 g / ha to 150 g / ha. In some embodiments, the compound of formula I is applied in an amount of 10 g / ha.

[0531] Compounds of formula I and compositions and mixtures containing compounds of formula I can be sprayed to control and / or prevent various fungal pathogens and related diseases. In some embodiments, the fungal pathogens are Leaf Blotch of Wheat (Mycosphaerella graminicola, anamorph Zymoseptoria tritici), Wheat Brown Rust (Puccinia triticina), Stripe Rust (Puccinia striiformis f. sp. tritici), Scab of Apple (Venturia inaequalis), Blister Smut of Maize (Ustilago maydis), Powdery Mildew of Grapevine (Uncinula necator), Barley scald (Rhynchosporium secalis), Blast of Rice (Magnaporche grisea), Rust of Soybean (Phakopsora pachyrhizi), Glume Blotch of Wheat (Leptosphaeria nodorum), Powdery Mildew of Wheat (Blumeria graminis f. sp. tritici), Powdery Mildew of Barley (Blumeria graminis f. sp.One of Powdery Mildew of Hordei (Erysiphe hordei), Powdery Mildew of Cucurbits (Erysiphe cichoracearum), Anthracnose of Cucurbits (Glomerella lagenarium), Leaf Spot of Beet (Cercospora beticola), Early Blight of Tomato (Alternaria solani), and Net Blotch of Barley (Pyrenophora teres).

[0532] In some embodiments, the fungal pathogen is Leaf Blotch of Wheat (Mycosphaerella graminicola, anamorph Zymoseptoria tritici), Wheat Brown Rust (Puccinia triticina), Stripe Rust (Puccinia striiformis f. sp. tritici), Scab of Apple (Venturia inaequalis), Blister Smut of Maize (Ustilago maydis), Powdery Mildew of Grapevine (Uncinula necator), Barley scald (Rhynchosporium secalis), Blast of Rice (Magnaporche grisea), Rust of Soybean (Phakopsora pachyrhizi), Glume Blotch of Wheat (Leptosphaeria nodorum), Powdery Mildew of Wheat (Blumeria graminis f. sp. tritici), Powdery Mildew of Barley (Blumeria graminis f. sp.One of Blumeria graminis f. sp. hordei), Powdery Mildew of Cucurbits (Erysiphe cichoracearum), Anthracnose of Cucurbits (Glomerella lagenarium), Leaf Spot of Beet (Cercospora beticola), Early Blight of Tomato (Alternaria solani), and Net Blotch of Barley (Pyrenophora teres).

[0533] In some embodiments, the fungal pathogen is Zymoseptoria tritici.

[0534] In some embodiments, the plant or soil disease is one of Septoria, Rust, Yellow Rust, Powdery Mildew, Rhyncosporium, Pyrenophora, Microdochium majus, Sclerotinia, Downy Mildew, Phytophthora, Cercosporea beticola, Ramularia, and ASR. Sigatoka negra.

[0535] The method of the present invention includes, but is not limited to, monocotyledonous plants such as sugarcane cereals, rice, maize (corn), and / or dicotyledonous crops such as beet (sugar beet or fodder beet, etc.); fruits (pome fruits, stone fruits, or soft fruits such as apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, or blackberries, etc.); leguminous plants (beans, lentils, peas, or soybeans, etc.); oil plants (rapeseed, mustard, poppy, olive, sunflower, coconut, castor oil plant, cocoa beans, or peanuts, etc.); cucumber plants (marrow, cucumber or melon, etc.); fiber plants (cotton, flax, hemp, or jute, etc.); citrus fruits (oranges, lemons, grapefruits, or mandarin oranges, etc.); vegetables (spinach, lettuce, cabbage, carrots, tomatoes, potatoes, cucurbitaceae plants, or bell peppers, etc.); laurel family (avocado, cinnamon, or camphor, etc.); tobacco; nuts; coffee; tea; vine plants; hops; durian; banana; natural rubber plants; and any crop including ornamental plants (flowers, shrubs, broad-leaved trees, or evergreen trees such as conifers, etc.).

[0536] In some embodiments, the plant is a monocotyledonous plant, more preferably a cereal. In certain embodiments, the cereal is wheat. In another specific embodiment, the cereal is triticale. In another specific embodiment, the cereal is rye. In another specific embodiment, the cereal is oats. In a further embodiment, the cereal is barley. In another specific embodiment, the cereal is triticale. In another embodiment, the crop is rice. In yet another embodiment, the crop is sugarcane. In yet another embodiment, the crop is corn.

[0537] In another embodiment, the crop is a dicotyledonous plant.

[0538] In one embodiment, the crop is rapeseed.

[0539] The compounds of formula I and compositions thereof can also be used as a seed treatment for preventing or controlling plant pathogens described in US Patent Application Publication No. 2018-0000082 (filed on January 4, 2018), the entire content of which is incorporated herein by reference.

[0540] The subject invention also provides a method for controlling or preventing fungal attack on a plant or protecting a plant from fungal attack, the method comprising applying any one of the compositions or mixtures disclosed herein to a seed adapted to produce a plant.

[0541] The subject invention also provides a method for treating a plant seed or seedling to produce a plant resistant to fungal attack, the method comprising applying any one of the compositions or mixtures disclosed herein to the plant seed or seedling. The subject invention also provides a method for protecting a plant from fungal attack, the method comprising applying any one of the compositions or mixtures disclosed herein to a nursery environment.

[0542] The subject invention also provides a plant resistant to fungal attack, wherein the plant seed is treated with any one of the compositions or mixtures disclosed herein.

[0543] The subject invention also provides a plant seed or seedling adapted to produce a plant resistant to fungal attack, wherein the plant seed or seedling is treated with any one of the compositions or mixtures disclosed herein.

[0544] The subject invention also provides a package comprising any one of the compositions or mixtures disclosed herein.

[0545] The subject invention also provides a package comprising any one of the compositions or mixtures disclosed herein.

[0546] The subject invention also provides for the use of any one of the mixtures disclosed herein for manufacturing a bactericidal composition. The subject invention also provides for the use of any one of the mixtures disclosed herein for manufacturing any one of the compositions disclosed herein.

[0547] Method for improving the stability of a liquid composition containing a compound of formula I: The present invention also relates to formula I:

[0548]

Chemical formula

[0549] The present invention also relates to formula I:

[0550]

Chemical formula

[0551] In some embodiments, the solubility of the compound of Formula I in the liquid carrier is less than 1000 ppm. In some embodiments, the solubility of the compound of Formula I in the liquid carrier is about 200 ppm. In some embodiments, the solubility of the compound of Formula I in the liquid carrier is about 80 ppm.

[0552] The present invention also provides a method for improving the stability of a liquid composition comprising a compound of Formula I:

[0553]

Chemical formula

[0554] In some embodiments, the pH of the composition is measured without further dilution or wetting. In some embodiments, the pH is measured after dilution or wetting with water.

[0555] In some embodiments, the pH of the composition is about 5. In some embodiments, the pH of the composition is about 5.5. In some embodiments, the pH of the composition is about 5.8. In some embodiments, the pH of the composition is about 6. In some embodiments, the pH of the composition is about 6.5. In some embodiments, the pH of the composition is about 7. In some embodiments, the pH of the composition is about 7.5.

[0556] In some embodiments, the method comprises adding a pH adjuster to the liquid composition.

[0557] The present invention also provides the use of a pH adjuster for improving the stability of an aqueous suspension concentrate (SC) composition comprising a compound of Formula I:

[0558]

Chemical formula

[0559] The present invention also provides a method for improving the stability of an aqueous suspension concentrate (SC) composition comprising a compound of Formula I:

[0560] [Chemical formula] Also provided is the use of a pH adjuster to improve the stability of an aqueous suspoemulsion (SE) composition containing a compound of .

[0561] The present invention also relates to Formula I:

[0562] [Chemical formula] Also provided is a method for improving the stability of a liquid composition containing a compound of and a liquid carrier, the method including maintaining the water content of the composition at less than 0.5% by weight based on the total weight of the composition.

[0563] The present invention also relates to Formula I:

[0564] [Chemical formula] Also provided is a method for improving the stability of a liquid composition containing a compound of and a liquid carrier, the method including adding (i) at least one stabilizing surfactant having crystal growth inhibition properties or (ii) a stabilizing system having crystal growth inhibition properties to the liquid composition.

[0565] In some embodiments, the stabilizing surfactant is a nonionic derivative of a polyalkylene oxide polyaryl ether. In some embodiments, the stabilizing surfactant is an anionic derivative of a polyalkylene oxide polyaryl ether.

[0566] In some embodiments, at least two stabilizing surfactants are added. In some embodiments, at least two stabilizing surfactants include at least one nonionic derivative of a polyalkylene oxide polyaryl ether and at least one anionic derivative of a polyalkylene oxide polyaryl ether.

[0567] The present invention also relates to Formula I:

[0568] [Chemical formula] Also provided is the use of at least one stabilizing surfactant having a polyalkylene oxide alkyl ether structure for controlling the solubility and / or decomposition of a compound of

[0569] In some embodiments, the stabilizing surfactant having a polyalkylene oxide polyaryl ether structure is a nonionic derivative of the polyalkylene oxide polyaryl ether. In some embodiments, the stabilizing surfactant having a polyalkylene oxide polyaryl ether structure is an anionic derivative of the polyalkylene oxide polyaryl ether.

[0570] In some embodiments, the method further includes selecting a liquid carrier, wherein the solubility of the compound of Formula I in the liquid carrier is less than 5000 ppm.

[0571] In some embodiments, the method further includes maintaining the pH value of the composition in the range of 5 to 7.5.

[0572] In some embodiments, the method further includes maintaining the water content of the composition at less than 0.5% by weight based on the total weight of the composition.

[0573] In some embodiments, the method further includes adding (i) at least one stabilizing surfactant having crystal growth inhibition properties or (ii) a stabilizing system having crystal growth inhibition properties to the liquid composition.

[0574] The present invention also provides a method for improving the stability of a liquid composition comprising a compound of Formula I:

[0575] [Chemical formula] and a liquid carrier, the method comprising formulating the composition to have a viscosity of at least 500 cP.

[0576] In some embodiments, the stable liquid composition is a thick suspension (SC) composition.

[0577] In some embodiments, the stable composition is a suspoemulsion (SE) composition.

[0578] In some embodiments, the stable liquid composition is an oil dispersion (OD) composition.

[0579] In some embodiments, the stable liquid composition is an emulsion (EC) composition.

[0580] In some embodiments, the mixture or composition is diluted before spraying. In some embodiments, the mixture or composition is diluted with water. The spraying rate of the diluted mixture or composition depends on the concentration of the active ingredient in the mixture or composition before dilution. Generally, the diluted mixture or composition is sprayed at a rate of about 5 L / ha to about 120 L / ha.

[0581] Method for preparing a composition comprising a compound of formula I The present invention provides a method for preparing a thick suspension (SC) composition disclosed herein, comprising: (1) mixing an agriculturally acceptable inert additive and an aqueous liquid carrier to obtain a premix; (2) adding a compound of formula I to the premix obtained in step (1) to obtain a mixture; and (3) grinding the mixture obtained in step (2) to obtain the desired composition. A method comprising the steps is provided.

[0582] In some embodiments, the method includes adding an additional additive to the mixture of step (2) before grinding the mixture.

[0583] The present invention provides a method for preparing a suspoemulsion (SE) composition disclosed herein, comprising: (1) mixing an agriculturally acceptable inert additive and an aqueous liquid carrier to obtain a premix; (2) Adding a compound of formula I and at least one adjuvant to the premix obtained in step (1) to obtain a mixture, and (3) Grinding the mixture obtained in step (2) to obtain the desired composition A method comprising is provided.

[0584] In some embodiments, step (1) includes adding a non-aqueous liquid carrier. In some embodiments, step (2) includes adding a non-aqueous liquid carrier. In some embodiments, the adjuvant added in step (2) is a non-aqueous liquid carrier.

[0585] The present invention is a method for preparing an oil dispersion (OD) composition disclosed herein, comprising (1) Mixing an agriculturally acceptable inert additive and a non-aqueous liquid carrier to obtain a premix, (2) Adding a compound of formula I to the premix obtained in step (1) to obtain a mixture, and (3) Grinding the mixture obtained in step (2) to obtain the desired composition A method comprising is provided.

[0586] The present invention is a method for preparing an emulsion (EC) composition disclosed herein, comprising (1) Mixing an agriculturally acceptable inert additive and a non-aqueous liquid carrier to obtain a premix, (2) Adding a compound of formula I to the premix obtained in step (1) to obtain a mixture, and (3) Filtering the solution of step (2) to obtain the desired composition A method comprising is provided.

[0587] Each embodiment disclosed herein is contemplated as being applicable to each other disclosed embodiment. Accordingly, all combinations of the various elements described herein are within the scope of the invention. Additionally, when an enumeration is presented, that enumeration shall be considered as a disclosure of any one of the elements of the enumeration.

[0588] The present invention will be better understood by reference to the details of the experiments described below, but those skilled in the art will readily understand that the specific detailed experiments are only illustrative of the invention, as it will be more fully described in the claims that follow. The present invention is illustrated by the following examples, but is not limited by these examples.

[0589] Experimental Section The compounds of formula I can be prepared as described in WO 2015 / 103144 and WO 2015 / 103142 pamphlets.

[0590] Preparing a stability composition containing the compound of formula I is difficult due to the high sensitivity of the compound. Numerous attempts have been made to stabilize the composition. Some of the results are described below.

[0591] The compounds of formula I were combined with adjuvants as tank mixes and / or as built-in compositions. Different types of adjuvants with different compositions were tested.

[0592] The adjuvants tested were polyvinylpyrrolidone (PVP), a block copolymer of vinylpyrrolidone and vinyl acetate (VP / VA), a siloxane polyalkylene oxide copolymer (Silwet® L-077), ethoxylated tridecyl alcohol 13 / 9 (Trycol®), an alkoxylated alcohol (Agnique® BP420), and a fatty acid methyl ester (Agnique® ME 18 RDF).

[0593] Example 1: 450 SC Composition without Adjuvant A concentrated suspension (SC) formulation containing 450 g / L of the compound of formula I and no adjuvant was prepared as follows.

[0594] Step I: Preparation of an agriculturally acceptable inert additive premix Soft water and Van Gel® B were charged into a container and mixed (high shear) to form a solution. The contents of the container were heated to 60 °C. SOPROPHOR® TS / 54 (TSP 54) was heated to 50 - 60 °C and slowly added to the container. Subsequently, Supragil® WP, Soprophor® 3D33, KH2PO4, Na2HPO4 and SAG 1572 were added to form a homogeneous solution.

[0595] Step II: Preparation of the compound of formula I The compound of formula I (40% w / w) was added to a premix containing a surfactant, and the suspension was milled in a bead mill (0.8 - 1.2 mm beads) until a particle size distribution with d90 < 5 μm was reached. The milled suspension was discharged from the reactor into a new container.

[0596] Step III: Completion of the composition Propylene glycol was added to the milled suspension and mixed until a uniform suspension was obtained. While mixing, soft water and AgRH 23 2% solution were added to the suspension until a viscosity of 1600 - 2200 cP was reached. The mixing was continued until a homogeneous solution was obtained. The viscosity was measured with a viscometer according to the CIPAC method MT 192.

[0597] The composition is summarized in Table 1.

[0598]

Table 1-1

[0599]

Table 1-2

[0600] Results of stability: The physical and chemical stability of the composition of Example 1 was tested under various conditions including CIPAC conditions. The results of the stability are summarized in Table 2.

[0601]

Table 2

[0602] The composition of Example 1 was stored at 54 °C for 2 weeks. No crystal growth was observed. The concentration of the compound of formula I was measured and was higher than 95%.

[0603] Example 2: A 450 SC composition containing a mixture of a copolymer of vinylpyrrolidone and vinyl acetate (VA / VP) A concentrated suspension (SC) formulation containing 450 g / L of the compound of formula I and a built-in adjuvant (VP / VA) was prepared as follows.

[0604] Step I: Preparation of an agriculturally acceptable inert additive premix Soft water and Van Gel® B were charged into a container and mixed (high shear) to form a solution. The contents of the container were heated to 60 °C. SOPROPHOR® TS / 54 (TSP 54) was heated to 50 - 60 °C and gradually added to the container. Supragil® WP, Soprophor® 3D33, KH2PO4, Na2HPO4 and SAG 1572 were added to the homogeneous solution.

[0605] Step II: Preparation of the compound of formula I The compound of formula I (40% weight / weight) was added to a premix containing a surfactant. The suspension was milled in a bead mill (0.8 - 1.2 mm beads) until a particle size of d90 < 5 μm was reached. The milled suspension was discharged from the reactor into a new container.

[0606] Step III: Completion of the composition Propylene glycol and VP / VA were added to the milled suspension until a uniform suspension was obtained. While mixing, soft water and a 2% solution of AgRH 23 were added to the suspension until a viscosity of 1600 - 2200 cP was reached. The mixing was continued until a homogeneous solution was obtained. The viscosity was measured with a viscometer according to the CIPAC method MT 192.

[0607] The compositions are summarized in Table 3.

[0608]

Table 3 - 1

[0609]

Table 3 - 2

[0610] Results of stability: The composition of Example 2 was stored at 54 °C for 2 weeks. No crystal growth was observed. The concentration of the compound of formula I was measured and was slightly lower than 95%.

[0611] Example 3: 450SC and 660SC Compositions Containing a Mixture of Vinylpyrrolidone / Vinyl Acetate Copolymer and Silwet® L - 077 A concentrated suspension (SC) formulation containing 450 g / L of the compound of formula I and two built - in adjuvants (VP / VA and Silwet® L - 077) on one hand, and 660 g / L of the compound of formula I and two built - in adjuvants (VP / VA and Silwet® L - 077) on the other hand, was prepared as follows.

[0612] Step I: Preparation of an agriculturally acceptable inert additive premix Soft water (and for the 450 SC composition, Van Gel® B) was charged into a container and mixed (high shear) to form a solution. The contents of the container were heated to 60 °C. SOPROPHOR® TS / 54 (TSP 54) was heated to 50 - 60 °C and slowly added to the container. Supragil® WP, Soprophor® 3D33, KH2PO4, Na2HPO4 and SAG 1572 were added to the homogeneous solution.

[0613] Step II: Preparation of the compound of formula I The compound of formula I (40% w / w) was added to a premix containing a surfactant. The suspension was milled in a bead mill (0.8 - 1.2 mm beads) until a particle size of d90 < 5 μm was reached. The milled suspension was discharged from the reactor into a new container.

[0614] Step III: Completion of the composition Propylene glycol and Silwet® L - 077 were added to the milled suspension until a uniform suspension was obtained. While mixing, soft water and a 2% solution of AgRH 23 were added to the suspension until a viscosity of 1600 - 2200 cP was reached. Mixing was continued until a homogeneous solution was obtained. The viscosity was measured with a viscometer according to the CIPAC method MT 192.

[0615] The 450 SC composition was summarized in Table 4 and the 660 SC composition was summarized in Table 5.

[0616]

Table 4 - 1

[0617]

Table 4 - 2

[0618] Results of stability: The composition of Table 4 was stored at 54 °C for 2 weeks. No crystal growth was observed. The concentration of the compound of Formula I was measured, and the concentration was slightly lower than 95%.

[0619]

Table 5-1

[0620]

Table 5-2

[0621] Results of stability: The stability results of the composition of Table 5 are summarized in Table 6 below.

[0622]

Table 6

[0623] Example 4: 450 SC Composition Containing Two Built-in Adjuvants A thick suspension (SC) formulation containing 450 g / L of the compound of Formula I and two built-in adjuvants (PVP and Silwet® L-077) was prepared as follows.

[0624] Step I: Preparation of an agriculturally acceptable inert additive premix Soft water and Van Gel® B were charged into a container and the solution was mixed (high shear). The contents of the container were heated to 60 °C. SOPROPHOR® TS / 54 (TSP 54) was heated to 50 - 60 °C and gradually added to the container. Then, Supragil® WP, Soprophor® 3D33, KH2PO4, Na2HPO4 and SAG were added.

[0625] Step II: Preparation of the compound of Formula I A compound of formula I (40% w / w) was added to a premix containing a surfactant therein to form a suspension. The suspension was milled in a bead mill (0.8 - 1.2 mm beads) until a particle size of d90 < 5 μm was reached. The suspension was discharged from the reactor into a new container.

[0626] Step III: Completion of the composition Propylene glycol and PVP were added to the milled suspension and mixed until a uniform suspension was obtained. While mixing, soft water and a 2% solution of Ag RH 23 were added until a viscosity of 1600 - 2200 cP was reached. Mixing was continued until the solution was homogeneous. The viscosity was measured with a viscometer according to the CIPAC method MT 192.

[0627] The composition is summarized in Table 7 below.

[0628]

Table 7 - 1

[0629]

Table 7 - 2

[0630] Example 5: 300 SE composition containing VP / VA, Agnique® BP 420 and Agnique® ME 18 RD - F A suspoemulsion (SE) composition containing 300 g / L of a compound of formula I and three built - in adjuvants (VP / VA, Agnique® BP 420 and Agnique® ME 18 RD - F) was prepared as follows.

[0631] Step I: Preparation of an agriculturally acceptable inert additive premix Soft water and Van Gel® B were charged into a container and mixed (high shear). The contents of the container were heated to 60 °C. SOPROPHOR® TS / 54 (TSP 54) was heated to 50 - 60 °C and gradually added to the container. Supragil® WP, Soprophor® 3D33, KH2PO4, Na2HPO4 and SAG were added to the solution.

[0632] Step II: Preparation of the compound of formula I The compound of formula I (40% w / w) was added to a premix containing a surfactant to form a suspension. The suspension was milled in a bead mill (0.8 - 1.2 mm beads) until a particle size of d90 < 5 μm was reached. The milled suspension was discharged from the reactor into a new container.

[0633] Step III: Preparation of the organic phase Agnique® ME RDF, Atlox™ 4914, Atlas™ G5002L, Genapol® X80 and Agnique® BP 420 were charged into a container and mixed until a homogeneous solution was obtained. The contents of the container were mixed (high shear) for at least 10 minutes until a droplet size of D90 = 10 μm was reached before adding SE to the suspension.

[0634] Step IV: Completion of the composition Propylene glycol and VP / VA were added to the milled suspension and mixed until a uniform suspension was obtained. The SE solution was gradually added to the milled suspension in three portions. Between each addition, Atlox™ 4913, soft water and Ag RH 23 2% solution were added while mixing until a viscosity of 1600 - 2200 cP was reached. Mixing was continued until a homogeneous solution was obtained. The viscosity was measured with a viscometer according to the CIPAC method MT 192.

[0635] The composition is summarized in Table 8 below.

[0636]

Table 8-1

[0637]

Table 8-2

[0638]

Table 8-3

[0639] Example 6: 300 SE Composition Containing PVP, Agnique® BP 420 and Agnique® ME 18 RD-F An SE composition containing 300 g / L of the compound of formula I and three built-in adjuvants (PVP, Agnique® BP 420 and Agnique® ME 18 RD-F) was prepared as follows.

[0640] Step I: Preparation of an agriculturally acceptable inert additive premix Soft water and Van Gel® B were charged into a container and mixed (high shear). The contents of the container were heated to 60 °C. SOPROPHOR® TS / 54 (TSP 54) was heated to 50 - 60 °C and gradually added to the container. Supragil® WP, Soprophor® 3D33, KH2PO4, Na2HPO4 and SAG were added to the solution.

[0641] Step II: Preparation of the compound of formula I The compound of formula I (40% weight / weight) was added to a premix containing a surfactant therein to form a suspension. The suspension was milled in a bead mill (0.8 - 1.2 mm beads) until a particle size of d90 < 5 μm was reached. The milled suspension was discharged from the reactor into a new container.

[0642] Step III: Preparation of the organic phase Agnique® ME RDF, Atlox™ 4914, Atlas® G5002L, Genapol® X80 and Agnique® BP 420 were charged into a container and mixed until a uniform solution was obtained. Before adding SE to the suspension, the contents of the container were mixed (high shear) for at least 10 minutes until a droplet size of D90 = 10 μm was reached.

[0643] Step IV: Completion of the composition Propylene glycol and PVP were added to the milled suspension and mixed until a uniform suspension was obtained. The SE solution was gradually added to the milled suspension in three portions. Between each addition, Atlox™ 4913, soft water and a 2% solution of Ag RH 23 were added with mixing until a viscosity of 1600 - 2200 cP was reached. Mixing was continued until a uniform solution was obtained. Viscosity was measured with a viscometer according to the CIPAC method MT 192.

[0644] The composition is summarized in Table 9 below.

[0645]

Table 9 - 1

[0646]

Table 9 - 2

[0647] Example 7: A thick suspension (SC) composition without a stabilizing surfactant at approximately pH 7 A thick suspension (SC) formulation containing 450 g / L of the compound of formula I and no stabilizing surfactant was prepared as follows.

[0648] 4% Atlox™ 4913, 2% Ethylan™ NS 500 LQ / Antarox® B 848, 0.5% Supragil® WP and 0.1% defoamer (SAG™ 1572) were added to water and mixed until a homogeneous solution was obtained.

[0649] While mixing (high shear), the compound of formula I was added. The mixing was carried out for 5 minutes. The mixture was placed in a Tinky with a few beads for 20 minutes.

[0650] The remaining material was put into the suspension, mixed, divided into vials and placed in the room and in the oven.

[0651] The formulations are summarized in Table 10.

[0652]

Table 10

[0653] Results of stability The SC composition was placed in the room temperature and in the oven (54 °C) for 24 hours and the concentration was examined. Crystalline particles were observed and the decomposition of the compound of formula I was measured. The results showed that the concentration of the compound of formula I decreased by more than 5%.

[0654] Example 8: Concentrated suspension composition containing stabilizing surfactants at pH 3.5 A concentrated suspension (SC) formulation containing 450 g / L of the compound of formula I and two stabilizing surfactants (Soprophor® 3D33 and Soprophor® TS / 54) was prepared as follows.

[0655] Step I: Preparation of an agriculturally acceptable inert additive premix Soft water was gradually added to a container containing preheated SOPROPHOR® TS / 54 (TSP 54). The contents of the container were mixed until a homogeneous solution was obtained and heated to 50 - 65 °C. Supragil® WP, Soprophor® 3D33, KH2PO4, Na2HPO4 and SAG™ 1572 were added to the solution.

[0656] Step II: Preparation of the compound of formula I The compound of formula I (40% w / w) was added to a premix containing a surfactant to form a suspension. The suspension was milled in a bead mill (0.8 - 1.2 mm beads) until a particle size of d90 < 5 μm was reached. The milled suspension was discharged from the reactor into a new container.

[0657] Step III: Completion of the composition Propylene glycol was added to the milled suspension and mixed until a uniform suspension was obtained. While mixing, soft water and a 2% solution of AgRH 23 were added to the suspension until a viscosity of 1600 - 2200 cP was reached. Mixing was continued until a homogeneous solution was obtained. The viscosity was measured with a viscometer according to the CIPAC method MT 192.

[0658] The composition is summarized in Table 11.

[0659]

Table 11-1

[0660]

Table 11-2

[0661] Results of stability: After 2 weeks in an oven at 54 °C, the concentration decreased by 6% in accelerated storage. A small amount of crystalline particles was observed. However, the concentration of the compound of formula I decreased.

[0662] Therefore, in order to have a stable SC formulation, the pH of the composition must be maintained in the range of 5.0 to 7.5.

[0663] Example 9: Concentrated suspension compositions containing stabilizing surfactants at pH 4 and 8 Table 12 shows two SC compositions (BN 161213-5-Sop3d_TSP54_PG and BN 161213-6-Sop3d_TSP54_PG), each containing two stabilizing surfactants (Soprophor® 3D33 and Soprophor® TS / 54). BN 161213-5-Sop3d_TSP54_PG has a low pH of 4, and BN 161213-6-Sop3d_TSP54_PG has a high pH of 8.

[0664] Neither composition was stable. In the first composition, the concentration decreased in the oven, and for the second composition, a significant increase in concentration was observed. Viscosity was measured with a viscometer according to CIPAC method MT 192.

[0665]

Table 12

[0666] When the pH is low, i.e., pH 4, the compound of formula I decomposes. In Example 12, the amount of the compound of formula I in the composition decreased from 44.4% by weight based on the total weight of the composition to 31.1% by weight based on the total weight of the composition. When the pH is high, the physical stability of the composition decreases. In Example 12, the composition became non-uniform and the viscosity increased.

[0667] As a conclusion, in order to have a stable SC formulation, it is necessary to maintain the pH of the composition in the range of 5.0 to 7.5.

[0668] Example 10: 250 OD composition containing Agnique ME 18 RD-F (OD composition A) An oil dispersion (OD) composition containing 250 g / L of the compound of formula I was prepared as follows.

[0669] Step I: Preparation of an inert additive premix in an agriculturally acceptable, non-aqueous carrier (fatty acid ester) Using a large-hole Silverson mixer, Bentone SD®-1 was added to Agnique® ME 18 RD-F under high shear (3000 rpm) and mixed for 5 minutes.

[0670] 10 seconds -1 The mixture was milled (50 times) in a colloid mill (IKA MagicLab) until the viscosity at no longer increased significantly. The viscosity was measured with a viscometer according to the CIPAC method MT 192.

[0671] Agnique® ME 18 RD-F was added to a suitable container, pregels were added, and the mixture was mixed for 5 minutes.

[0672] Emulsifiers and dispersants were added and mixed for 15 minutes until homogeneous.

[0673] Step II: Preparation of the compound of formula I The compound of formula I was added with stirring and mixed until homogeneous. After all the active ingredients were added, the mixture was mixed for 15 minutes.

[0674] Step III: Completion of the composition The sample was milled in an Eiger mini motor mill (80% filled with 0.75 mm - 1.0 mm beads, 4000 rpm) for 15 minutes.

[0675] The formulations are summarized in Table 13.

[0676] [Table 13]

[0677] Example 11: 250 OD Composition (OD Composition B) Containing Agnique® ME 18 RD-F An oil dispersion (OD) composition containing 250 g / L of the compound of formula I was prepared as follows.

[0678] Step I: Preparation of an Inert Additive Premix in an Agriculturally Acceptable, Non-Aqueous Carrier (Fatty Acid Ester) Using a large-hole Silverson mixer, Bentone SD®-1 was added to Agnique® ME 18 RD-F under high shear (3000 rpm) and mixed for 5 minutes.

[0679] 10 seconds -1 The mixture was milled (50 times) in a colloid mill (IKA MagicLab) until the viscosity at

[0680] Agnique® ME 18 RD-F was added to a suitable container, pregel was added, and the mixture was mixed for 5 minutes.

[0681] An emulsifier and a dispersant were added and mixed for 15 minutes until homogeneous.

[0682] Step II: Preparation of the Compound of Formula I The compound of formula I was added with stirring and mixed until homogeneous. After all the active ingredients were added, the mixture was mixed for 15 minutes.

[0683] Step III: Completion of the Composition The sample was milled in an Eiger mini motor mill (80% filled with 0.75 mm - 1.0 mm beads, 4000 rpm) for 15 minutes.

[0684] The formulations are summarized in Table 14.

[0685]

Table 14

[0686] The composition of Example 11 was physically stable (phase separation was observed, but it was uniform after mixing). After storage at 54 °C for 2 weeks, chemical decomposition was observed (less than 10% of the compound of formula I decomposed).

[0687] Example 12: 250 OD composition containing Agnique® ME 18 RD-F (OD composition C): An oil dispersion (OD) composition containing 250 g / L of the compound of formula I was prepared using the same process as in Examples 10 and 11.

[0688] The formulations are summarized in Table 15.

[0689] [Table 15]

[0690] The composition of Example 12 was stored at 54 °C for 2 weeks, but no significant decomposition of the compound of formula I was observed.

[0691] Example 13: 250 OD composition containing Agnique® ME 18 RD-F (OD composition D): Step I: Preparation of an inert additive premix in an agriculturally acceptable, non-aqueous carrier (fatty acid ester) Agnique® ME 18 RD-F was added to a suitable container, pregels were added, and the mixture was stirred for 5 minutes.

[0692] The emulsifier and dispersant were added and the mixture was stirred for 15 minutes until homogeneous.

[0693] Step II: Preparation of the compound of formula I The compound of formula I was added with stirring and the mixture was stirred until homogeneous. After all the active ingredients were added, the mixture was stirred for 15 minutes.

[0694] 10 seconds -1The mixture was milled (50 times) in a colloid mill (IKA MagicLab) until the viscosity in it no longer increased significantly. The viscosity was measured with a viscometer according to the CIPAC method MT 192.

[0695] Step III: Completion of the composition The sample was milled in an Eiger mini motor mill (80% filled with 0.75 mm - 1.0 mm beads, 4000 rpm) for 15 minutes.

[0696] [Table 16]

[0697] [Table 17]

[0698] Example 14: EC composition containing the compound of formula I Three emulsion (EC) compositions (A, B and C) containing 50 g / L of the compound of formula I respectively were prepared.

[0699] The process for preparing composition C is summarized below. (Compositions A and B can be prepared using a similar process.) 1. Alkamuls® 14 / R (CO60) was melted in a warm bath / oven at 50 °C. 2. Benzyl acetate and propylene carbonate were added to this container and heated to 50 °C. 3. The compound of formula I was added to the reactor while mixing until a clear solution was obtained. 4. Ninate® 60, TSP16 and molten Alkamuls® 14 / R (4) were gradually added to the reactor while mixing until a clear solution was obtained. 5. Mixing was continued for 1 hour while cooling the reactor to room temperature. 6. The solution was discharged from the reactor through a filter (5 μm).

[0700] Compositions A, B, and C are summarized in Tables 18, 19, and 20, respectively. The stability results for Compositions B and C are summarized in Tables 21 and 22.

[0701]

Table 18

[0702] Crystal formation was observed in this formulation after 1 week at 0 °C and after several weeks at room temperature.

[0703]

Table 19

[0704]

Table 20

[0705]

Table 21-1

[0706]

Table 21-2

[0707]

Table 22

[0708] Example 15: Tank mix of a composition comprising a compound of Formula I and an adjuvant Example 15(a): SC composition tank mixed with an adjuvant Wheat crops (winter wheat plants at the BBCH 12 growth stage, cultivar Alixan (Limagrain)) were treated with compositions comprising a compound of Formula I and an adjuvant at different concentrations as a built-in composition and / or as a tank mix application.

[0709] All the compositions and mixtures tested were prepared with a volume of water equivalent to 200 L / ha and used 3 hours after preparation.

[0710] The SC composition of Example 1 was mixed with Trycol® (0.2 or 0.4 L per hectare) or Silwet® (0.01 L per hectare), which were added as a tank mix into 200 L of water.

[0711] The compositions and mixtures were sprayed with a hand-held sprayer at an operating pressure of 2 bar. For each test condition, three replicates (pots) of six wheat plants were used.

[0712] After treatment, the wheat plants were dried at room temperature for 1 hour and then cultivated in a growth chamber (temperature of 24 °C during the day / 18 °C at night - photoperiod of 16 hours of light / 8 hours of darkness, and relative humidity of 65%).

[0713] Cut fragments of the first leaf are transferred to Petri dishes containing adapted agar (six leaf fragments per Petri dish). The fragments are inoculated with a calibrated conidial suspension of the wheat pathogen (Z. tritici) strain Mg Tri-R6.

[0714] After inoculation, the Petri dishes are cultivated in a growth chamber (temperature of 20 °C during the day / 17 °C at night - photoperiod of 16 hours of light / 8 hours of darkness, controlled relative humidity).

[0715] After a 21-day cultivation period, the intensity of the infection, i.e., the surface of the leaf colonized by the wheat pathogen (Z. tritici) strain, is evaluated (quantitative criterion). Then, the bactericidal effect in each composition is determined as a percentage of the untreated control. All data are processed by statistical software (XL STAT). The output expected at this step is the ranking of the biological bactericidal effect of the compounds of formula I in the presence of different adjuvants.

[0716] Disease evaluation was performed 21 days post inoculation (dpi) by measuring the length of the leaf fragments that had necrosed. Subsequently, the intensity of infection was determined as a percentage of the total length of the leaf fragments.

[0717] Efficacy was calculated based on the area under the disease progress curve (AUDPC), a quantitative measure of disease intensity over time. The trapezoidal method, which is the most commonly used method for estimating AUDPC, was performed by multiplying the mean disease intensity between each pair of adjacent time points by the corresponding time interval, and this was done for each time interval.

[0718] The bactericidal effect was determined from the AUDPC values and expressed as a percentage of the untreated control.

[0719] Results and Discussion All adjuvants were tested individually against the wheat pathogen (Zymoseptoria tritici) strain Mg Tri - R6. None of the adjuvants tested had any significant bactericidal activity individually against the wheat pathogen (Z. tritici) strain Mg Tri - R6 under control conditions.

[0720] The results are summarized in Figures 1 - 6.

[0721] The results show that the addition of an adjuvant increases the efficacy of the compound of formula I against the wheat pathogen (Zymoseptoria tritici) strain Mg Tri - R6.

[0722] As shown in Figures 1 and 2, the addition of one adjuvant, Trycol® or Silwet® (even in small amounts), increased the efficacy and the actual bactericidal activity of the compound of formula I compared to spraying without an adjuvant.

[0723] The results showed that the bactericidal effect of the composition was significantly improved by adding Trycol® or Silwet® in a tank mix to the compound SC of formula I.

[0724] While not wishing to be bound by any theory, it is hypothesized that Silwet® L-077 and Trycol (the concentration of this adjuvant is up to 3% by weight based on the total weight of the composition) improve the bactericidal effect of the composition by reducing the surface tension of the leaf surface.

[0725] As shown in FIGS. 4, 5 and 6, by adding two adjuvants, Silwet® or Agnique® BP 420, and PVP or VP / VA, the effectiveness and practical bactericidal activity of the compound of formula I were increased compared to spraying without adjuvant.

[0726] The effectiveness of the compound of formula I in the presence of PVP or VP / VA combined with Agnique® BP 420 (alcohol ethoxylate propoxylate C16 C18) or Silwet® was increased compared to spraying the compound of formula I without adjuvant.

[0727] While not wishing to be bound by any theory, it is hypothesized that Silwet® L-077 (siloxane polyalkylene oxide copolymer) combined with VP / VA (the concentration of this adjuvant is up to 2% by weight based on the total weight of the composition) reduces the surface tension, and thereby increases the effectiveness and practical bactericidal activity of the compound of formula I by spreading the composition on the leaf surface. In other words, the deposit of the composition on the leaf surface spreads more on the leaf and remains for a longer time, and thus has rainfast properties.

[0728] Example 15(b): EC composition tank-mixed with adjuvant The EC formulation and the adjuvant were mixed immediately before the experiment (e.g., as a tank mix).

[0729] All fungicides are prepared with water or S solution (S solution refers to the solution obtained by diluting the composition) in a volume equivalent to 200 L / ha and used 3 hours after preparation.

[0730]

Table 23

[0731] The results are summarized in Figures 7 and 8.

[0732] Example 16: OD composition To evaluate the fungicidal activity of the OD composition containing the compound of formula I, the OD composition (from Example 10, Table 13) was prepared with water or S solution (S solution refers to the solution obtained by diluting the composition) in a volume equivalent to 200 L / ha and used 3 hours after preparation.

[0733] The first leaves of wheat nutrient bodies, cultivar Alixan, were left untreated or treated with 10 g a.i. / ha and 20 g a.i. / ha 21 days after inoculation with pycnidiospores of the wheat pathogen (Zymoseptoria tritici) strain Mg Tri-R6 (moderately resistant to DMI fungicides and highly resistant to Qol fungicides under controlled conditions) using the OD formulation prototype A of the compound of formula I (from Example 10, Table 13). The disease was evaluated using the intensity of infection.

[0734] The results are shown in Figure 9.

[0735] Example 17: OD composition and EC composition containing adjuvant To evaluate the fungicidal activity of the OD composition and EC composition containing an adjuvant and the compound of formula I against potato blight (Phytophthora infestans), the OD composition (from Example 10, Table 13) was prepared with water or S solution in a volume equivalent to 300 L / ha and sprayed using a backpack sprayer with a horizontal boom flat fan nozzle (sprayed for 6 weeks). The EC composition used was EC composition C (Example 14, Table 21).

[0736] The disease was evaluated using the percentage of infection. The results are shown in Figure 10. The invention described in the present specification may include the following aspects. [1] (a) A bactericidally effective amount of a compound of formula I:

Chemical formula

[10] The adjuvant is (i) a polyalkylene oxide alkyl ether, (ii) a siloxane polyalkylene oxide copolymer, (iii) an ester of a fatty acid, (iv) vinylpyrrolidone and its derivatives, and (v) a sugar-based surfactant The stability liquid composition according to the above [9], which is selected from the group consisting of.

[11] (a) a bactericidally effective amount of a compound of formula I:

Chem.

[12] The bactericidal mixture according to the above

[11] , wherein the bactericidal mixture is a composition or a tank mix.

[13] a) the amount of the compound of formula I in the mixture is between 1% and 99% by weight based on the total weight of the mixture, b) the amount of the adjuvant in the mixture is between 0.1% and 99% by weight based on the total weight of the mixture, c) the amounts of the compound of formula I and the adjuvant in the bactericidal mixture are about 0.1% to 99% by weight based on the total weight of the mixture, and / or d) the weight ratio of the compound of formula I to the adjuvant is from 50:1 to 1:50, The bactericidal mixture according to the above

[11] or

[12] .

[14] a) the adjuvant is a derivative of vinylpyrrolidone, b) the adjuvant is a siloxane polyalkylene oxide copolymer, c) the adjuvant is polyvinylpyrrolidone, d) the adjuvant is a C16 - C18 alcohol ethoxylated propoxylated ether, e) the adjuvant is ethoxylated tridecyl alcohol or polyoxyethylene(9) isotridecanol, f) the adjuvant is a blend of a fatty acid ester and a fatty alcohol alkoxylate, and / or g) the adjuvant is a mixture of a methylated seed oil and a polyglycerol ester, the bactericidal mixture according to any one of

[11] to

[13] above.

[15] The bactericidal mixture according to

[14] above, wherein the derivative of vinylpyrrolidone is a block copolymer of vinylpyrrolidone and vinyl acetate (VP / VA).

[16] a) the amount of VP / VA in the mixture is about 0.5 - 3% by weight based on the total weight of the mixture, or b) the mixture is a concentrated suspension composition, and the concentration of VP / VA in the concentrated suspension composition is about 0.5 - 2.5% by weight based on the total weight of the composition, the bactericidal mixture according to

[15] above.

[17] (i) A method for controlling and / or preventing fungal pathogen attack on plants or (ii) fungal diseases of plants and / or soil, the method comprising spreading the composition or mixture according to any one of [1] to

[16] above on the soil, plants, roots, leaves, seeds, fungal habitats, and / or the location where invasion is to be prevented, thereby controlling and / or preventing fungal pathogen attack on plants or fungal diseases of plants and / or soil.

[18] (i) A method for controlling and / or preventing fungal pathogen attack on plants or (ii) fungal diseases of plants and / or soil, the method comprising spreading a bactericidally effective amount of a compound having the formula (I):

Chem.

[19] A method for improving the biological activity of a compound of formula I against a fungal pathogen, The method comprises spraying a compound of formula I in the presence of at least one adjuvant, thereby improving the biological activity of the compound of formula I,

Chem.

[20] b) The adjuvant is a block copolymer of vinyl pyrrolidone and vinyl acetate (VP / VA), c) The adjuvant is a siloxane polyalkylene oxide copolymer, d) The adjuvant is polyvinyl pyrrolidone, e) The adjuvant is a C16-C18 alcohol ethoxylated propoxylated ether, f) The adjuvant is ethoxylated tridecyl alcohol or polyoxyethylene (9) isotridecanol, g) The adjuvant is a blend of a fatty acid ester and a fatty alcohol alkoxylate, and / or h) The adjuvant is a mixture of a methylated seed oil and a polyglycerol ester, The method according to

[18] or

[19] above. a) The compound of formula I is sprayed in an amount in the range of 5 g / ha to 150 g / ha,

[21] b) The compound of formula I and the adjuvant are sprayed simultaneously or sequentially, c) The compound of formula I and the adjuvant are tank-mixed, d) The compound of formula I and the adjuvant are formulated as a single composition, and / or e) Two or more adjuvants are sprayed, wherein at least one of the adjuvants is tank-mixed with the compound of formula I, and at least one of the adjuvants is formulated with the compound of formula I, The method according to any one of

[18] to

[20] above. ​

[22] a) the fungal pathogen is wheat leaf blight (Mycosphaerella graminicola, anamorph: Zymoseptoria tritici), wheat brown rust (Puccinia triticina), stripe rust (Puccinia striiformis f. sp. tritici), scab of apple (Venturia inaequalis), blister smut of maize (Ustilago maydis), powdery mildew of grapevine (Uncinula necator), barley scald (Rhynchosporium secalis), blast of rice (Magnaporthe grisea), rust of soybean (Phakopsora pachyrhizi), glume blotch of wheat (Leptosphaeria nodorum), powdery mildew of wheat (Blumeria graminis f. sp. tritici), powdery mildew of barley (Blumeria graminis f. sp.one of Blumeria graminis f. sp. hordei, Powdery Mildew of Cucurbits (Erysiphe cichoracearum), Anthracnose of Cucurbits (Glomerella lagenarium), Leaf Spot of Beet (Cercospora beticola), Early Blight of Tomato (Alternaria solani), or Net Blotch of Barley (Pyrenophora teres), or... b) the mycotic disease of the plant or soil is one of brown spot (Septoria), red rust, yellow rust, powdery mildew, barley leaf stripe (rhyncosporium), net blotch (pyrenophora), wheat pink mold (Microduchium majus), sclerotinia, downy mildew, Phytophthora, sugar beet brown spot (Cercosporea beticola), leaf spot (Ramularia), Sigatoka disease (ASR. Sigatoka negra.) The method according to any one of

[18] to

[21] above.

[23] Formula I:

Chem.

[24] Formula I:

Chem.

[25] Formula I:

Chem.

[26] Formula I:

Chem.

[27] Formula I:

Chem.

[28] Formula I:

Chem.

[29] A method for (i) controlling or preventing fungal attack on a plant or (ii) protecting a plant from fungal attack, comprising applying the composition or mixture according to any one of [1] to

[16] above to seeds adapted to produce the plant.

[30] A method of treating plant seeds or seedlings to produce plants resistant to fungal attack, comprising applying the composition or mixture according to any one of [1] to

[16] above to the plant seeds or seedlings.

[31] A method of protecting plants from fungal attack, comprising applying the composition or mixture according to any one of [1] to

[16] above to a seedling environment.

[32] A plant resistant to fungal attack, wherein the plant seeds are treated with the composition or mixture according to any one of [1] to

[16] above.

[33] Plant seeds or seedlings adapted to produce plants resistant to fungal attack, wherein the plant seeds or seedlings are treated with the composition or mixture according to any one of [1] to

[16] above.

[34] A package comprising the composition or mixture according to any one of [1] to

[16] above.

[35] Use of the mixture according to any one of

[11] to

[16] above for producing a fungicidal composition.

[36] (i) For the control and / or prevention of fungal attack on plants and / or (ii) for the control and / or prevention of fungal diseases of plants and / or soil, the composition or mixture according to any one of the above [1] to

[16] , or the use of the composition or mixture according to any one of the above [1] to

[16] for (i) the control and / or prevention of fungal attack on plants and / or (ii) the control and / or prevention of fungal diseases of plants and / or soil.

[37] (a) For the control and / or prevention of fungal pathogen attack on plants and / or (b) for the control and / or prevention of fungal diseases of plants and / or soil, a compound of formula (I):

Chem.

[38] (a) For the control and / or prevention of fungal pathogen attack on plants and / or (b) for the control and / or prevention of fungal diseases of plants and / or soil, a compound of formula (I):

Chem.

[39] Formula (I):

Chem.

[40] Formula (I):

Chem.

Claims

1. (a) A compound of formula I: 【Chemical 1】 and (b) A liquid carrier A stable liquid composition comprising, wherein (i) When the liquid carrier is an aqueous liquid carrier, the pH of the composition is between 5 and 7.5, the composition comprises a stabilizing surfactant, and the concentration of the compound of formula I in the stable liquid composition is 150 g / L to 750 g / L, (ii) When the liquid carrier is a non-aqueous carrier, the composition has a water content of less than 0.5% by weight based on the total weight of the composition, and the concentration of the compound of formula I in the stable liquid composition is 50 g / L to 750 g / L. A stable liquid composition.

2. The stable liquid composition according to claim 1, wherein the liquid carrier is an aqueous liquid carrier.

3. The stable liquid composition according to claim 2, wherein the pH of the composition is in the range of 6 to 7.

5.

4. The stable liquid composition according to claim 2, wherein the pH of the composition is in the range of 6 to 7.

5. a) The composition comprises a pH adjuster, b) The composition comprises 30% to 70% by weight of an aqueous liquid carrier based on the total weight of the composition, and / or c) The concentration of the compound of formula I in the stable liquid composition is 150 g / L to 750 g / L, The stable liquid composition according to any one of claims 2 to 4.

6. The stable liquid composition according to any one of claims 2 to 5, wherein the composition is a thick suspension (SC) composition and the compound of formula I is suspended in the aqueous carrier.

7. The stable liquid composition according to any one of claims 2 to 5, wherein the composition is a suspoemulsion (SE) composition, the compound of formula I is suspended in the aqueous carrier, and the composition comprises a non-aqueous liquid component in the aqueous carrier.

8. The stable liquid composition according to any one of claims 2 to 7, wherein the stabilizing surfactant is a combination of a non-ionic stabilizing surfactant and an anionic stabilizing surfactant.

9. The stable liquid composition according to any one of claims 2 to 8, wherein the stabilizing surfactant is effective in controlling the solubility and / or decomposition of the compound of formula I.

10. The stable liquid composition according to any one of claims 2 to 9, wherein the stabilizing surfactant has a structure of polyalkylene oxide polyaryl ether.

11. The stabilizing surfactant is tristyrylphenol ethoxylate phosphate ester, 2,4,6-tri-(1-phenylethyl)-phenol polyglycol ether having 54 EO, ethoxylated tristyrylphenol, or any combination thereof, the stability liquid composition according to any one of claims 2 to 9.

12. The composition contains two stabilizing surfactants, and the stabilizing surfactant is tristyrylphenol ethoxylate phosphate ester and ethoxylated tristyrylphenol, the stability liquid composition according to any one of claims 2 to 9.

13. The liquid carrier is a non-aqueous liquid carrier, the stability liquid composition according to claim 1.

14. a) The non-aqueous liquid carrier is selected from the group consisting of aromatic hydrocarbons, paraffins, petroleum, diesel, mineral oils, esters and / or amides of fatty acids, tall oil fatty acids, polyalkylene oxide alkyl ethers, siloxane polyalkylene oxide copolymers, esters of fatty acids, vinyl pyrrolidone and its derivatives, sugar-based surfactants, and any combination thereof, b) The composition contains 30% to 80% by weight of the non-aqueous liquid carrier based on the total weight of the composition, c) The composition has a water content of less than 0.2% by weight based on the total weight of the composition, d) The composition contains a stabilizing surfactant and / or e) The composition does not contain phosphoric acid, urea, propyl gallate, dimethyl sulfoxide (DMSO), morpholine and / or N-methylpyrrolidone, The stability liquid composition according to claim 13.

15. The composition is an oil dispersion (OD) composition, and the solid particles of the compound of formula I are suspended in the non-aqueous carrier, the stability liquid composition according to claim 13 or 14.

16. The composition is an emulsion (EC) composition, and the compound of formula I is dissolved in the non-aqueous carrier, the stability liquid composition according to claim 13 or 14.

17. a) The solubility of the compound of formula I in the liquid carrier is less than 5000 ppm, and / or b) The composition has a viscosity of 500 cP to 3000 cP, The stability liquid composition according to any one of claims 1 to 16.

18. a) The composition contains agriculturally acceptable inert additives, and the agriculturally acceptable inert additives are selected from the group consisting of surfactants, dispersants, emulsifiers, wetting agents, defoamers, solvents, co-solvents, light stabilizers, ultraviolet absorbers, radical scavengers and antioxidants, adhesives, neutralizing agents, thickeners, binders, sequestering agents, biocides, buffers, preservatives, and antifreeze agents; b) The composition further contains a solid diluent, a liquid diluent, a wetting agent, an adhesive, a thickener, a defoamer, a preservative, an antioxidant, a binder, a fertilizer, an antifreeze agent, an additional pesticide, a toxicity reducer, or any combination thereof, and / or c) The composition does not contain phosphoric acid, urea, propyl gallate, dimethyl sulfoxide (DMSO), morpholine, and / or N-methylpyrrolidone; The stable liquid composition according to any one of claims 1 to 17.

19. The composition further contains an adjuvant, and the adjuvant is as follows: (i) Polyalkylene oxide alkyl ether, (ii) Siloxane polyalkylene oxide copolymer, (iii) Ester of fatty acid, (iv) Vinylpyrrolidone and its derivatives, and (v) Sugar-based surfactant The stable liquid composition according to any one of claims 1 to 18, which is selected from the group consisting of.

20. a) The amount of the adjuvant in the composition is between 0.1% and 99% by weight based on the total weight of the mixture, and / or b) The weight ratio of the compound of formula I to the adjuvant is 50:1 to 1:

50. The stable liquid composition according to claim 19.

21. a) The adjuvant is a derivative of vinylpyrrolidone, b) The adjuvant is a siloxane polyalkylene oxide copolymer, c) The adjuvant is polyvinylpyrrolidone, d) The adjuvant is C16-C18 alcohol ethoxylated propoxylated ether, e) The adjuvant is ethoxylated tridecyl alcohol or polyoxyethylene (9) isotridecanol, f) The adjuvant is a blend of a fatty acid ester and a fatty alcohol alkoxylate, and / or g) The adjuvant is a mixture of a methylated seed oil and a polyglycerol ester. The stable liquid composition according to claim 19 or 20.

22. The stability liquid composition according to any one of claims 19 to 21, wherein the composition contains isotridecyl alcohol polyglycol ether, ethoxylated propoxylated alcohol or C16-C18 alcohol ethoxylated propoxylated ether.

23. The stability liquid composition according to any one of claims 19 to 22, wherein the composition contains C16-C18 alcohol ethoxylated propoxylated ether.

24. The stability liquid composition according to any one of claims 19 to 23, wherein the composition contains a siloxane polyalkylene oxide copolymer.

25. The stability liquid composition according to any one of claims 19 to 24, wherein the composition contains rapeseed oil methylated ester.

26. The stability liquid composition according to any one of claims 19 to 25, wherein the composition contains a block copolymer of vinylpyrrolidone and vinyl acetate (VP / VA).

27. a) the amount of VP / VA in the mixture is 0.5 to 3% by weight based on the total weight of the mixture, or b) the composition is a concentrated suspension composition, and the concentration of VP / VA in the concentrated suspension composition is 0.5 to 2.5% by weight based on the total weight of the composition. The stability liquid composition according to claim 26.

28. A method for controlling and / or preventing (i) fungal pathogen attack on plants or (ii) fungal diseases of plants and / or soil, wherein the method comprises spraying the composition according to any one of claims 1 to 27 onto the soil, plants, roots, leaves, seeds, fungal habitats, and / or the location where invasion is to be prevented, thereby controlling and / or preventing fungal pathogen attack on plants or fungal diseases of plants and / or soil.

29. The method includes spraying at least one adjuvant, and the adjuvant is i. polyalkylene oxide alkyl ether, ii. siloxane polyalkylene oxide copolymer, iii. ester of fatty acid, iv. vinylpyrrolidone and its derivatives, and v. sugar-based surfactant The method according to claim 28, which is selected from the group consisting of.

30. a) at least two adjuvants are sprayed, or the compound of formula I is sprayed in the presence of at least two adjuvants, b) the adjuvant is a block copolymer of vinyl pyrrolidone and vinyl acetate (VP / VA), c) the adjuvant is a siloxane polyalkylene oxide copolymer, d) the adjuvant is polyvinyl pyrrolidone, e) the adjuvant is a C16-C18 alcohol ethoxylated propoxylated ether, f) the adjuvant is ethoxylated tridecyl alcohol or polyoxyethylene (9) isotridecanol, g) the adjuvant is a blend of a fatty acid ester and a fatty alcohol alkoxylate, and / or h) the adjuvant is a mixture of a methylated seed oil and a polyglycerol ester, The method according to claim 29.

31. The method according to claim 29 or 30, wherein the adjuvant is a C16-C18 alcohol ethoxylated propoxylated ether.

32. a) spraying the compound of formula I and the adjuvant simultaneously or sequentially, b) tank mixing the compound of formula I and the adjuvant, c) formulating the compound of formula I and the adjuvant as a single composition, and / or d) spraying two or more adjuvants, wherein at least one of the adjuvants is tank mixed with the compound of formula I, and at least one of the adjuvants is formulated with the compound of formula I, The method according to any one of claims 29 to 31.

33. a) spraying the compound of formula I in an amount in the range of 5 g / ha to 150 g / ha, and / or b) the fungal pathogen is wheat leaf blotch (Mycosphaerella graminicola, anamorph: Zymoseptoria tritici), wheat brown rust (Puccinia triticina), stripe rust (Puccinia striiformis f. sp. tritici), scab of apple (Venturia inaequalis), blister smut of maize (Ustilago maydis), powdery mildew of grapevine (Uncinula necator), barley scald (Rhynchosporium secalis), blast of rice (Magnaporthe grisea), rust of soybean (Phakopsora pachyrhizi), glume blotch of wheat (Leptosphaeria nodorum), powdery mildew of wheat (Blumeria graminis f. sp. tritici), powdery mildew of barley (Blumeria graminis f. sp.one of powdery mildew of cucurbits (Erysiphe cichoracearum), anthracnose of cucurbits (Glomerella lagenarium), leaf spot of beet (Cercospora beticola), early blight of tomato (Alternaria solani), and net blotch of barley (Pyrenophora teres), or... the mycotic disease of the plant or soil is one of Septoria, red rust, yellow rust, powdery mildew, rhyncosporium, pyrenophora, Microduchium majus, Sclerotinia, Downy mildew, Phytophthora, Cercosporea beticola, Ramularia, ASR. Sigatoka negra., The method according to any one of claims 28 to 32.

34. The method according to any one of claims 28 to 33, wherein the fungal pathogen is the wheat pathogen (Zymoseptoria tritici) strain Mg Tri-R6.

35. Formula I: [Chemical Formula 2] A method for improving the stability of a liquid composition comprising a compound of formula I and a liquid carrier, comprising: (i) when the liquid carrier is an aqueous carrier, the method comprises maintaining the pH value of the composition in the range of 5 to 7.5 and adding at least one stabilizing surfactant to the composition; (ii) when the liquid carrier is a non-aqueous carrier, the concentration of the compound of formula I in the composition is 50 g / L to 750 g / L, and the method comprises maintaining the water content of the composition at less than 0.5% by weight based on the total weight of the composition.

36. Formula I: [Chemical Formula 3] Use of at least one stabilizing surfactant having the structure of a polyalkylene oxide polyaryl ether for controlling the solubility and / or decomposition of a compound of formula I, wherein the polyalkylene oxide polyaryl ether is a compound having an aryl group substituted with at least two aromatic groups.

37. Formula I: 【Chemical Formula 4】 A method for preparing a concentrated suspension (SC) composition according to claim 6, comprising a compound of formula I, the method comprising: The method comprises: (1) mixing an agriculturally acceptable inert additive and an aqueous liquid carrier to obtain a premix; (2) adding the compound of formula I to the premix obtained in step (1) to obtain a mixture; and (3) grinding the mixture obtained in step (2) to obtain the desired composition. A method comprising.

38. Formula I: 【Chemical Formula 5】 A method for preparing a suspoemulsion (SE) composition according to claim 7, comprising a compound of formula I, the method comprising: The method comprises: (1) mixing an agriculturally acceptable inert additive and an aqueous liquid carrier to obtain a premix; (2) adding the compound of formula I and at least one adjuvant to the premix obtained in step (1) to obtain a mixture; and (3) grinding the mixture obtained in step (2) to obtain the desired composition. A method comprising.

39. Formula I: 【Chemical Formula 6】 A method for preparing an oil dispersion (OD) composition according to claim 15, comprising a compound of formula I, the method comprising: The method comprises: (1) mixing an agriculturally acceptable inert additive and a non-aqueous liquid carrier to obtain a premix; (2) adding the compound of formula I to the premix obtained in step (1) to obtain a mixture, and (3) grinding the mixture obtained in step (2) to obtain the desired composition A method comprising.

40. Formula I: 【Chemical Formula 7】 A method for preparing an emulsion (EC) composition according to claim 16, comprising a compound of The method comprises (1) mixing an agriculturally acceptable inert additive and a non-aqueous liquid carrier to obtain a premix, (2) adding the compound of formula I to the premix obtained in step (1) to obtain a mixture, and (3) filtering the solution of step (2) to obtain the desired composition A method comprising.

41. A method for (i) controlling or preventing fungal attack on a plant or (ii) protecting a plant from fungal attack, comprising applying a composition according to any one of claims 1 to 27 to a seed adapted to produce a plant.

42. A method of treating a plant seed or seedling to produce a plant resistant to fungal attack, comprising applying a composition according to any one of claims 1 to 27 to the plant seed or seedling.

43. A method of protecting a plant from fungal attack, comprising applying a composition according to any one of claims 1 to 27 to a nursery environment.

44. A plant whose seeds have been treated with a composition according to any one of claims 1 to 27 and which is resistant to fungal attack.

45. A plant seed or seedling adapted to produce a plant resistant to fungal attack, wherein the plant seed or seedling has been treated with a composition according to any one of claims 1 to 27.

46. A package comprising a composition according to any one of claims 1 to 27.

47. A composition according to any one of claims 1 to 27 for use in (i) controlling and / or preventing fungal attack on a plant and / or (ii) controlling and / or preventing a mycotic disease of a plant and / or soil.

48. Use of a composition according to any one of claims 1 to 27 for (i) controlling and / or preventing fungal attack on a plant and / or (ii) controlling and / or preventing a mycotic disease of a plant and / or soil.

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