Mixtures and compositions comprising 5-fluoro-4-imino-3- methyl-1-tosyl-3,4-dihydropyrimidin-2-one, and methods of use thereof

Abstract

To provide a fungicidal mixture and a method for controlling and / or preventing fungal pathogen attack on a plant.SOLUTION: The present invention provides a fungicidal mixture comprising (a) a fungicidally effective amount of a compound of Formula I and (b) at least one adjuvant selected from the group consisting of: (i) polyalkylene oxide alkyl ether; (ii) siloxane polyalkyleneoxide copolymer; (iii) esters of fatty acid; (iv) vinylpyrrolidones and derivatives thereof; and (v) sugar-based surfactants. When the fungicidal mixture is a composition, the amount of the adjuvant is at least 3 wt.% based on the total weight of the composition. When the fungicidal mixture is a tank mix, the ratio between the sugar-based surfactant and the compound of Formula I is from 50:1 to 1:50.SELECTED DRAWING: None

Description

[Technical field]

[0001] This application is the benefit of U.S. Provisional Patent Application No. 62 / 755,866, filed November 5, 2018. No. 6,399,433, filed on Dec. 13, 2003, the entire contents of which are incorporated herein by reference.

[0002] Throughout this application, various publications are referenced. The disclosures of these publications in their entireties are set forth at: No. 6,393,635, which is incorporated herein by reference in order to more fully describe the state of the art to which this invention pertains. do. [Background technology]

[0003] background Fungicides act to protect plants from damage caused by fungi Fungicides are compounds of natural or synthetic origin that have a potent antimicrobial effect. Current agricultural practices rely on the use of fungicides. In fact, some crops cannot be grown profitably without the use of fungicides. The use of fungicides allows growers to improve yields and crop quality, resulting in improved crop health. In most situations, the increase in crop value is due to the use of fungicides. is worth at least three times its usage cost.

[0004] 5-Fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidine 2(1H)-ones (compounds of formula I) are useful in treating, but not limited to, wheat leaf spot pathogens. Produced by Zymoseptoria tritici (SEPTTR) and fungi of the classes Ascomycota and Basidiomycota Provides control of a variety of pathogens, including diseases, that adversely affect economically important crops It is a disinfectant.

[0005] Use of N3-substituted-N1-sulfonyl-5-fluoropyrimidinone derivatives as fungicides This use is described in U.S. Patent No. 8,263,603, issued September 11, 2012. , the entire contents of which are incorporated herein by reference. The preparation of 1-tosyl-3,4-dihydropyrimidin-2(1H)-one is U.S. Patent No. 9,850,215 issued December 26, 2007 and U.S. Patent No. 9,850,215 issued December 12, 2017 No. 9,840,476, the entire contents of each of which are incorporated herein by reference. It is incorporated by reference in the notes.

[0006] U.S. Patent No. 8,263,603 also describes a method for controlling or preventing fungal attack. US201002326333A1 -Substituted-N1-sulfonyl-5-fluoropyrimidinone derivatives and plant biology - Google Patents DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS A disinfectant composition comprising a commercially available carrier material, as well as methods for its use, have been described.

[0007] Bactericidal compositions are often formulated under a variety of conditions and / or with adjuvants and The fungicidal composition is applied together with other additives such as fertilizers and insecticides. They must exhibit excellent chemical stability and a high level of physical stability during the application and dispensing process. Must be.

[0008] In agriculture, compositions are often diluted with water before use. Liquid compositions are diluted and then mixed with water. It is much easier to disperse it in

[0009] Currently, 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidinyl Stable liquid compositions of din-2(1H)-ones are not available in the art. 5-Fluoro-4-imino-3-methyl-2-phenylpropanediol in the control and / or prevention of fungal infestations on objects The extraordinary efficacy of 1-tosyl-3,4-dihydropyrimidin-2(1H)-one In consideration of this, 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyridine There is a great need in the art for stable liquid compositions containing mydin-2(1H)-one. It is said that.

[0010] In some cases, the bioactivity and efficacy of fungicides may be affected by rapid drift, limited foliage, and / or other factors. This is limited for a variety of reasons, including poor permeation, and high surface tension / low diffusivity. The effectiveness of the active compounds can be influenced and enhanced by the addition of adjuvants.

[0011] Adjuvants are inactive substances added to improve the performance of active ingredients and their compositions. Adjuvants are active chemicals that affect the absorption and delivery properties of active ingredients. Adjuvants act by acting as a catalyst to enhance the efficacy and activity of the active ingredient. It is possible to enhance the efficacy of the active ingredient, for example by improving the properties of the spray solution to improve the foliar delivery of the fungicide. Improves deposition.

[0012] The use of an adjuvant suitable for the active ingredient and its composition is often necessary to make the active ingredient more effective. The aim of this study is to determine whether Ajuba can be used in the treatment of malaria and whether it can act with full efficacy after application. The nutrient is then added to increase the reservoir of material "available" for uptake on the leaf surface. Such adjuvants include non-ionic surfactants or various types of This is often made from sesame oil.

[0013] U.S. Pat. No. 8,263,603 discloses the N3-substituted-N1-sulfo compounds described therein. Formulations containing 5-fluoro-1-methylpyrimidinone derivatives are useful for the prevention and treatment of toxic compounds in target crops and organisms. May additionally contain adjuvant surfactants to enhance adhesion, wetting and penetration In improving upon U.S. Patent No. 8,263,603, the inventors of that application disclosed The adjuvant used was 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-diaminobutyric acid. have been shown to be particularly effective in enhancing the fungicidal efficacy of hydropyrimidin-2(1H)-ones. Found it. Summary of the Invention

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

[0015] [ka] and (b) Liquid carrier The present invention provides a stable liquid composition comprising:

[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 moisture content of less than 0.5% by weight based on the total weight of the composition. In an embodiment, the composition has a viscosity of at least 500 cP (or mPa·s). In some embodiments, the composition has a viscosity of from 500 cP to 3000 cP.

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

[0018] [ka] and (b) (i) polyalkylene oxide alkyl ethers, (ii) siloxane polyalkylene oxide copolymers, (iii) esters of fatty acids, (iv) Vinylpyrrolidone and its derivatives, and (v)sugar-based surfactant At least one adjuvant selected from the group consisting of The present invention provides a disinfectant mixture comprising:

[0019] The present invention relates to a method for controlling fungal pathogen attack on plants and / or A method of prevention comprising administering to soil any one of the compositions or mixtures described herein. , plants, roots, leaves, seeds, location of fungus, and / or methods to prevent infestation and applying the fungus to a location where the fungus is likely to be present, thereby controlling and / or preventing fungal pathogen infestation of the plant. Also provided is a method comprising:

[0020] The present invention relates to a method for preventing fungal diseases of plants and / or soil. A method for the prevention and / or elimination of any of the compositions or mixtures described herein. 1. Apply the species to the soil, plants, roots, leaves, seeds, fungal location, and / or areas where you are trying to prevent infestation. and / or spraying the fungus in the soil and / or in the soil to control fungal diseases. Also provided are methods, including preventing.

[0021] The present invention relates to a method for controlling and / or preventing fungal pathogen infestation in plants, comprising the steps of: A therapeutically effective amount of a compound of formula (I):

[0022] [ka] and at least one adjuvant are applied to soil, plants, roots, leaves, seeds, fungi, spraying in areas where infestations are to be prevented, thereby preventing infestations of plants; and controlling and / or preventing fungal pathogen infestation, wherein the adjuvant (i) polyalkylene oxide alkyl ethers, (ii) siloxane polyalkylene oxide copolymers, (iii) esters of fatty acids, (iv) Vinylpyrrolidone and its derivatives, and (v) Sugar surfactants Also provided is a method, wherein the method is selected from the group consisting of:

[0023] The present invention is a method for controlling and / or preventing fungal diseases in plants and / or soil. A fungicidally effective amount of a compound of formula (I):

[0024] [ka] and at least one adjuvant are applied to soil, plants, roots, leaves, seeds, fungi, spraying at the location of the infestation and / or where infestation is to be prevented, thereby preventing the growth of plants and and / or to control and / or prevent fungal diseases in soil, wherein the adjuvant (i) polyalkylene oxide alkyl ethers, (ii) siloxane polyalkylene oxide copolymers, (iii) esters of fatty acids, (iv) Vinylpyrrolidone and its derivatives, and (v) Sugar surfactants Also provided is a method, wherein the method is selected from the group consisting of:

[0025] The present invention provides a method for improving the biological activity of a compound of formula I against a fungal pathogen, comprising administering to said compound at least In the presence of at least one adjuvant,

[0026] [ka] and applying the compound of formula I to the skin, thereby improving the biological activity of the compound of formula I. Bunt, (i) polyalkylene oxide alkyl ethers, (ii) siloxane polyalkylene oxide copolymers, (iii) esters of fatty acids, (iv) Vinylpyrrolidone and its derivatives, and (v) Sugar surfactants The method is selected from the group consisting of:

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

[0028] [ka] and a liquid carrier, comprising: 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 1000 It is less than ppm.

[0029] The present invention relates to a compound of formula I:

[0030] [ka] A method for improving the stability of a liquid composition comprising a compound of formula (I) and a liquid carrier, comprising: Also provided is a method comprising maintaining the pH value in the range of 5 to 7.5.

[0031] The present invention relates to a compound of formula I:

[0032] [ka] Improve the stability of aqueous suspension concentrate (SC) compositions containing the compound The use of a pH adjuster to increase the pH is also provided.

[0033] The present invention relates to a compound of formula I:

[0034] [ka] The present invention improves the stability of aqueous suspoemulsion (SE) compositions containing the compound. The use of a pH adjuster to increase the pH is also provided.

[0035] The present invention relates to a compound of formula I:

[0036] [ka] A method for improving the stability of a non-aqueous liquid composition comprising a compound of formula (I) and a liquid carrier, comprising: The method also includes maintaining the moisture content of the composition at less than 0.5% by weight based on the total weight of the composition. Provide.

[0037] The present invention relates to a compound of formula I:

[0038] [ka] A method for improving the stability of a non-aqueous liquid composition comprising a compound of formula (I) and a liquid carrier, comprising: The method also includes maintaining the moisture content of the composition at less than 0.2% by weight based on the total weight of the composition. Provide.

[0039] The present invention relates to a compound of formula I:

[0040] [ka] 2. A method for improving the stability of a liquid composition comprising a compound of formula (I) and a liquid carrier, comprising: (ii) at least one stabilizing surfactant having crystal growth inhibiting properties; Also provided is a method that includes adding a stabilizing system having the properties to a liquid composition.

[0041] The present invention relates to a compound of formula I:

[0042] [ka] Polyalkylene oxide polyarylsulfones for controlling the solubility and / or degradation of compounds of the present invention The present invention also provides the use of at least one stabilizing surfactant having a diol ether structure.

[0043] The present invention relates to a compound of formula I:

[0044] [ka] A method for improving the stability of a liquid composition comprising a compound of formula (I) and a liquid carrier, the method comprising: and formulating the composition to have a viscosity of at least 500 cP.

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

[0046] In some embodiments, the method further comprises adding additional additives to the mixture prior to grinding the mixture in step (2). The method includes adding to the mixture of

[0047] The present invention relates to a method for preparing the suspoemulsion (SE) compositions disclosed herein. There was, (1) Mixing an agriculturally acceptable inert additive with an aqueous liquid carrier to obtain a premix. Step (2) The compound of formula I and at least one adjuvant are mixed with the protease obtained in step (1). adding to the remix to obtain a mixture; and (3) milling the mixture obtained in step (2) to obtain the desired composition. The present invention provides a method comprising:

[0048] The present invention provides a method for preparing the oil dispersion (OD) compositions disclosed herein, comprising the steps of: (1) Mix an agriculturally acceptable inert additive with a non-aqueous liquid carrier to form a premix. obtaining a step of (2) Adding a compound of formula I to the premix obtained in step (1) to obtain a mixture. Tep, and (3) milling the mixture obtained in step (2) to obtain the desired composition. The present invention provides a method comprising:

[0049] The present invention relates to an emulsifiable concentrate (EC) composition as disclosed herein. A method of preparing (1) Mix an agriculturally acceptable inert additive with a non-aqueous liquid carrier to form a premix. obtaining a step of (2) Adding a compound of formula I to the premix obtained in step (1) to obtain a mixture. Tep, and (3) filtering the solution of step (2) to obtain the desired composition. The present invention provides a method comprising: [Brief description of the drawings]

[0050] [Figure 1] Graph showing the effect of Trycol® low (referred to as 0.2 L / ha), Trycol® (referred to as 0.4 L / ha) or Silwett as adjuvants on the activity of the compound of formula I. Comparison of the area under the disease progression curve (AUDPC) determined from the intensity of infection with the wheat pathogen (Z. tritici) strain Mg Tri-R6, moderately resistant to DMI fungicide and highly resistant to Qol fungicide, measured at 21 dpi (days post inoculation) of wheat plants, cultivar Alixan, untreated or treated with the compound of formula I 450 concentrated suspension composition used at two rates (0.028 and 0.014 L / ha) alone (no adjuvant) or with adjuvant as a tank mix. Values ​​of observations at the same time points followed by the same letter are not significantly different (p<0.05) by the Newman-Keuls test. [Diagram 2] 1 is a graph showing the effect of Trycol® low (referred to as 0.2 L / ha), Trycol® (referred to as 0.4 L / ha) or Silwett adjuvants on the activity of the compound of formula I. A comparison of the fungicidal efficacy of the compound of formula I 450 concentrated suspension composition used at two rates (0.028 and 0.014 L / ha) alone (no adjuvant) or with one rate of adjuvant (Trycol® low, Trycol® or Silwett®) against the wheat pathogen Z. tritici strain Mg Tri-R6, which is moderately resistant to DMI fungicides and highly resistant to Qol fungicides, in control conditions, obtained from AUDPC values. [Diagram 3]Graph showing the effect of the combination of two adjuvants, PVP and AGNIQUE BP420, as a built-in composition, on the activity of the compound of formula I. Comparison of the area under the disease progression curve (AUDPC) determined from the intensity of infection of wheat plants, cultivar Alixan, which are untreated or treated with the compound of formula I 450 concentrated suspension composition alone (without adjuvant) or with adjuvant, measured at 21 dpi, with the wheat pathogen (Z. tritici) strain Mg Tri-R6, which is moderately resistant to DMI fungicide and highly resistant to Qol fungicide. Values ​​of observations at the same time points followed by the same letter are not significantly different (p<0.05) by the Newman-Keuls test. [Figure 4] 1 is a graph showing the effect of the combination of two adjuvants, PVP and AGNIQUE® BP420, as a built-in composition on the activity of the compound of formula I. 2 is a comparison of the fungicidal activity of a concentrated suspension composition of the compound of formula I at 10 g ai / ha against the wheat pathogen Zymoseptoria tritici strain Mg Tri-R6, which is moderately resistant to DMI fungicides and highly resistant to Qol fungicides, under controlled conditions, obtained from AUDPC values. [Diagram 5] 1 is a graph showing the effect of three adjuvant combinations, PVP and AGNIQUE® BP420, VP / VA and Silwett, and VP / VA and AGNIQUE® BP420, as built-in compositions (450 suspension concentrate composition) on the activity of the compound of formula I. Disease rating (intensity of infection) on the first leaves of wheat plantlets, cultivar Alixan, untreated or treated with the suspension concentrate composition of the compound of formula I at 10 g ai / ha, 21 days after inoculation with pycnospores of Zymoseptoria tritici strain Mg Tri-R6, moderately resistant to DMI fungicides and highly resistant to Qol fungicides, under control conditions. Values ​​of observations at the same time points followed by the same letter are not significantly different (P<0.05) by the Newman-Keuls test. [Figure 6] Compound of Formula I Figure 1 shows the effect of three adjuvant combinations, PVP and AGNIQUE® BP420, VP / VA and Silwett®, and VP / VA and AGNIQUE® BP420, as built-in compositions, on the activity of the compound of Formula I (450 concentrated suspension composition).Fungicidal efficacy from the intensity of infection determined with concentrated suspension composition of the compound of Formula I at 10 g ai / ha at 21 dpi against the wheat pathogen Zymoseptoria tritici strain Mg Tri-R6, which is moderately resistant to DMI fungicides and highly resistant to Qol fungicides, under control conditions. [Figure 7] 1 is a graph showing a comparison of the area under the disease progression curve (AUDPC) determined from the intensity of infection of wheat plants, cultivar Alixan, with the wheat pathogen (Z. tritici) strain Mg Tri-R6, moderately resistant to DMI fungicides and highly resistant to Qol fungicide, measured at 21 and 28 dpi, treated with the compound 50 EC composition of formula I at two rates (0.25 and 0.125 L / ha) of untreated or composition A alone (no adjuvant / additive) or with adjuvant (Trycol®) and composition B alone (no adjuvant / additive) or with adjuvant (Trycol® low, Trycol®, Synergen® SOC). Values ​​of observations at the same time points followed by the same letter are not significantly different (p<0.05) according to the Newman-Keuls test. [Figure 8]1 is a graph showing a comparison of fungicidal efficacy of compound 50 emulsion compositions of formula I at two rates (0.25 and 0.125 L / ha) of composition A alone (no adjuvant) or with adjuvant (Trycol®) and composition B alone (no adjuvant / additive) or with adjuvants (Trycol® low, Trycol®, Synergen® SOC) against wheat pathogen (Z. tritici) strain Mg Tri-R6, which is moderately resistant to DMI fungicides and highly resistant to Qol fungicides, under controlled conditions, obtained from AUDPC values. [Figure 9] FIG. 1 is a graph showing disease rating (intensity of infection) on first leaves of wheat vegetative plantlets, cultivar Alixan, untreated or treated with OD formulation prototype A of the compound of formula I at 10 g ai / ha and 20 g ai / ha, 21 days after inoculation with pycnospores of the wheat pathogen Zymoseptoria tritici strain Mg Tri-R6, which is moderately resistant to DMI fungicides and highly resistant to Qol fungicides, under control conditions. [Figure 10] 1 is a graph showing disease rating (% infection) for potato late blight (Phytophthora infestans). Field trial rating after 6 weeks of application. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0051] Detailed Description of the Invention definition Unless otherwise defined, all technical and scientific terms used herein are defined as follows: has the meaning commonly understood by those of ordinary skill in the art to which the subject matter pertains.

[0052] The terms "a" or "an" are not specifically defined herein. Thus, the terms "a," "an," "the," and "the )" or "at least one" may be used interchangeably in this application.

[0053] As used herein, the term "about" when used in connection with a numerical value means ±10% of the stated value. In addition, all ranges directed to the same component or property herein are inclusive and These are independent and combinable, including all intermediate points and ranges. When provided, all integers within that range and their decimal places are also within the scope of the present invention. For example, "0.1~80%" is a range of 0.1%, 0.2%, 0.3%, etc. Up to 80% inclusive.

[0054] As used herein, the term "plant" or "crop" refers to the entire plant, plant organs (e.g., leaves, stems, This includes references to plant parts (such as twigs, roots, trunks, branches, shoots, fruits, etc.), plant cells, or plant seeds. The term also encompasses the harvest of the plant, such as fruit. The plant contains reproductive parts such as seeds and cuttings and tubers that can be used for plant propagation. It may also include its propagation material, which may include plant growth material, such as seeds, tubers, spores, corms, etc. , bulbs, rhizomes, basal shoots, stolons, and buds, as well as other parts of the plant (emerging (including seedlings and young plants that are transplanted after they sprout or emerge from the soil).

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

[0056] As used herein, the term "mixture" or "combination" refers to any It refers to combinations of physical forms, for example, blends, solutions, alloys, etc.

[0057] As used herein, the term "effective amount" refers to an amount sufficient to achieve a good level of control when applied. This refers to the amount of a compound that is sufficient for

[0058] As used herein, the phrase "agriculturally acceptable" means that the use in agricultural / pesticidal applications is within the skill of the art. It means what is known and accepted in the art.

[0059] As used herein, the term "adjuvant" refers to an adjuvant that is not a bactericide in itself, but is used to As any substance that enhances or is intended to enhance the effectiveness of a fungicide in Broadly defined, adjuvants include, but are not limited to, spreading agents, penetrating agents, compatibilizers, As used herein, the term "additive" may be understood to include additives, additives, and drift retardants. Any substance added to the composition that is not a bactericide per se, such as a binder, surfactant, It is defined as a synergist, buffer, acidifier, antifoam and thickener.

[0060] As used herein, the term "built-in" refers to additives such as insecticides, adjuvants and other additives. It is meant that all of the ingredients are contained in the same composition.

[0061] As used herein, the term "tank mix" refers to a mixture of at least One insecticide and / or additive and / or adjuvant are mixed in the spray This means that...

[0062] As used herein, the phrase "agriculturally acceptable carrier" refers to a composition for agricultural or horticultural use. By carrier is meant a carrier known and accepted in the art for the formulation of the product.

[0063] As used herein, the term "thickener" refers to a thickener that enhances the viscosity of a liquid without essentially changing the other properties of the composition. Refers to an auxiliary that increases the viscosity of a 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 reference to chemical stability, e.g. If the composition is chemically stable, the composition may be formulated according to the Manual on Development, the entire contents of which are incorporated herein by reference. pment and Use of FAO and WHO Specification for Pesticides(First Edition - Third Revision)(``FAO / WHO Manual'')(http: / / www.fao.org / agriculture / crops / thematic -sitemap / theme / pests / jmps / manual / en / ) This means that the product meets the chemical stability criteria described in the FAO / WHO Manual. After storing at 54±2℃ for 14 days, and then at 50±2℃ for 4 weeks, After storage at 45±2°C for 6 weeks, after storage at 40±2°C for 8 weeks, After 12 weeks of storage at 2°C or 18 weeks of storage at 30±2°C, the composition A composition is stable if no significant degradation of the active ingredient in the composition is observed. The amount of degradation permitted before being considered as occurring depends on the concentration of the active ingredient in the composition. Compositions containing more than 25 and up to 100 g / L of active ingredient as described in the FAO / WHO Manual For products, degradation of up to 10% of the active ingredient is considered to be insignificant degradation, and degradation of more than 100 to a maximum of 25 For compositions containing 0 g / L of active ingredient, a maximum of 6% degradation of the active ingredient is considered to be insignificant degradation. and for compositions containing more than 250 up to 500 g / L of active ingredient, a maximum of 5% of the active ingredient Degradation of the active ingredient is considered to be insignificant, and for compositions containing more than 500 g / L of the active ingredient, a maximum of 2 Degradation of 5 g / L of active ingredient is considered as insignificant degradation.

[0066] As used herein, the term "stability" when used in reference to physical stability, e.g. If the composition is physiologically stable and when used in conjunction with the composition, the composition complies with the International Pesticide Analysis Collaborative International Pesticides Analytical Council (CIPAC) CIPAC is a certification body for pesticides that meets the physical stability criteria described by the FDA. CIP is an international organization that promotes international agreements on analytical and physicochemical testing methods for pharmaceuticals. Methods adopted by AC can be found at https: / / www.cipac.org / index.php / methods-publications The methods are published in the CIPAC Handbooks available online at This is incorporated in the petition.

[0067] As used herein, the term "stabilizing surfactant" refers to a surfactant that is added to a liquid composition containing a compound of formula I. Any surfactant that enhances the physical and / or chemical stability of the compound of formula I when applied to the compound. In some embodiments, the stabilizing surfactant is defined as a stabilizing agent that inhibits crystal growth. It is effective for.

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

[0069] As used herein, the term "w / w" refers to the weight percentage based on the total weight of a composition or mixture. It means stage.

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

[0071] Compounds of formula I may be provided with sensitive groups such as sulfonyl groups and correspondingly at the N1 and C4 positions. These "groups" are pro-pesticide derivatives of N3-Me-5-FU that contain the imine In addition, highly sensitive compounds that require the development of specific conditions to stabilize the compound of formula I in liquid compositions. In addition, the compound of formula I has several crystalline forms, making it difficult to utilize. These drugs tend to form large crystals, affecting their rate of penetration into the target.

[0072] The formulation of a composition containing an active ingredient often involves the use of surfactants, dispersants, emulsifiers, wetting agents, , defoamers, solvents, co-solvents, light stabilizers, UV absorbers, radical scavengers and antioxidants, Adhesives, neutralizing agents, thickeners, binders, sequestering agents, biocides, buffers Preservatives and agriculturally acceptable inert additives such as antifreeze agents are required. The addition of additives can affect the solubility of the active ingredient and can result in chemically and physically unstable compositions. bring about.

[0073] Solvents and additives that can be used with compounds of formula I should be neutral, i.e. It is necessary that the compound does not contain any active functional groups that may affect its stability and cause its decomposition. The solvents and / or excipients used to formulate the compounds of formula I are The compound is not reactive to the above compounds.

[0074] Functional groups that may affect the stability of the compounds of formula I include SO, OH, and non-sterically hindered amines. The compounds of formula I in an amide solvent are N- and / or O-containing groups such as aryl and amines. It was found that the chemical stability of the compound depends on the substituents of the amide. Alternatively, the reactivity of the excipients may be important in formulating a stable composition containing the compound of formula I. A reactive nucleophilic group is a hydroxyl group with a bond dissociation energy of less than 120 Kcal / mol. , weakly dissociated hydrogen bonds, or acidic functional groups.

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

[0076] For the reasons stated above, formulating compounds of formula I in liquid compositions is particularly difficult.

[0077] The stability of the compound of formula I in the liquid carrier controls the solubility of the compound of formula I in the liquid carrier. controlling the pH of the composition in the aqueous environment; controlling the water content of the composition; Adding a surfactant effective to prevent growth and / or control the viscosity of the composition It was found that this could be improved by

[0078] Stable liquid compositions containing compounds of formula I, as well as methods of use and preparation thereof, are described below. Write down.

[0079] Stable liquid composition: The present invention relates to (a) a fungicidally effective amount of a compound of formula I:

[0080] [ka] and (b) a liquid carrier. The present invention provides a stable liquid composition comprising:

[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 to 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 further comprises a stabilizing system. include.

[0083] In some embodiments, the composition comprises at least one anionic stabilizing surfactant. In some embodiments, the composition includes at least one non-ionic stabilizing surfactant. In some embodiments, the composition comprises two stabilizing surfactants. In some embodiments, the composition comprises a stabilizing system comprising a non-ionic stabilizing surfactant and an ionic surfactant. The combination includes a soluble stabilizing surfactant.

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

[0085] In some embodiments, the pH of the composition ranges from 5 to 7.5. 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. H 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. Water may be present in the composition as a liquid carrier. Water may also be present as a result of dilution or wetting. It may be present in the composition.

[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. do.

[0088] In some embodiments, the liquid carrier is water and the pH of the composition is adjusted with further dilution and / or In some embodiments, the liquid carrier is a non-aqueous carrier, and the composition is The pH of the article 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 is 0.5 parts by weight based on the total weight of the composition. %, preferably less than 0.2% by weight based on the total weight of the composition.

[0092] In some embodiments, the non-aqueous composition comprises less than 0.5% by weight of the total composition. In some embodiments, the non-aqueous composition has a water content of 0.4 parts by weight based on the total weight of the composition. In some embodiments, the non-aqueous composition has a moisture content of less than about 100% by weight of the total composition. In some embodiments, the non-aqueous composition has a moisture content of less than 0.3% by weight. In some embodiments, the non-aqueous composition has a moisture content of less than 0.2% by weight based on the total weight of the composition. The article has a moisture content of less than 0.1% by weight based on the total weight of the composition.

[0093] Less than 0.5% by weight relative to the total weight of the composition, preferably less than 0.2% by weight relative to the total weight of the composition The amount of water less than 100% by weight may include, but is not limited to, the amount of water added to the composition prior to adding the components of the composition to the composition. Drying and / or hydration of the ingredients (both active and inactive) in the composition This can be achieved by using methods including reducing the moisture content of the composition. Uses low moisture content surfactants, low moisture content carriers, water scavengers and / or desiccants The control may be performed by

[0094] In some embodiments, the composition comprises a surfactant with a low water content. The composition comprises a carrier having a low moisture content. In some embodiments, the composition comprises at least one water-soluble polymer. In some embodiments, the composition comprises at least one desiccant. In embodiments, a low moisture content surfactant, a low moisture content carrier, a water scavenger and / or a desiccant is added to the composition after it has dried.

[0095] In some embodiments, the water scavenger is tetraethyl orthosilicate, Dynasylan ( In some embodiments, Dy is selected from the group consisting of Dy Nasylan® is Dynasylan® P. The scavenger reduces the water content of the non-aqueous liquid composition to less than 0.5% by weight, improving the stability of the composition. These water scavengers reduce the moisture content of the OD composition to less than 0.5% by weight, improving the composition. These water scavengers improve the stability of the EC composition by reducing the moisture content to less than 0.5% by weight. to improve the stability of the composition.

[0096] In some embodiments, the amount of water scavenger in the composition is about 0.5 to about 100 parts by weight of the total composition. It is 7.5% by weight.

[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 to 3000 cP. The composition has a viscosity of 500 cP to 2500 cP. In some embodiments, the composition has a viscosity of 1600 cP to 3000 cP. In some embodiments, the composition has a viscosity of 3000 cP or less. Has a degree.

[0098] In some embodiments, the composition has a viscosity of about 500 cP to 1000 cP. In an embodiment, the composition has a viscosity of about 1000 cP to 1500 cP. In some embodiments, the composition has a viscosity of about 1500 cP to 2000 cP. In some embodiments, the composition has a viscosity of about 2000 cP to 2500 cP. The product has a viscosity of about 2500 cP to 3000 cP.

[0099] In some embodiments, the composition has a pH of about 500 cP, about 600 cP, about 700 cP, about 80 0cP, approx. 900cP, approx. 1000cP, approx. 1100cP, approx. 1200cP, approx. 1300 cP, approx. 1400cP, approx. 1500cP, approx. 1600cP, approx. 1700cP, approx. 1800 cP, approx. 1900cP, approx. 2000cP, approx. 2100cP, approx. 2200cP, approx. 2300 cP, approx. 2400cP, approx. 2500cP, approx. 2600cP, approx. 2700cP, approx. 2800 cP, about 2900 cP, and about 3000 cP.

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

[0103] In some embodiments, the compound of formula I is in the form of solid particles. Solid particles of the compound of formula I are suspended in an aqueous carrier. In some embodiments, the compound of formula I The solid particles of the product are suspended in a non-aqueous carrier.

[0104] In some embodiments, the compound of formula I is dissolved in a non-aqueous carrier.

[0105] When solid particles of a compound of formula I are suspended in an aqueous carrier, the composition is called a concentrated suspension (SC). It is.

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

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

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

[0109] In some embodiments, the stable liquid composition is a concentrated suspension (SC) composition. In 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 concentrate (EC) composition. It is a composition.

[0110] In some embodiments, the stable liquid composition comprises at least one stabilizing surfactant. In some embodiments, the stable liquid composition is a concentrated suspension (SC) composition. It is a suspension concentrate (SC) composition that includes a formulated surfactant.

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

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

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

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

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

[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 c It has a viscosity of less than P.

[0117] In some embodiments, the stable liquid composition is a concentrated suspension (SC) composition, In some embodiments, the stable liquid composition has a viscosity of at least 500 cP. It 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 concentrated suspension (SC) composition, and the SC composition is In some embodiments, the stable liquid composition has a viscosity of from 1600 cP to 2200 cP. It is a concentrated 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 comprises at least 50 In some embodiments, the composition comprises a non-aqueous liquid carrier, The composition has a viscosity of less than 3000 cP.

[0119] In some embodiments, the stable liquid composition is an oil dispersion (OD) composition, and the OD composition In some embodiments, the stable liquid composition comprises an oil-based composition having a viscosity of at least 500 cP. It is a 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 is 2 It has a viscosity of 500 cP or less.

[0120] Viscosity was determined using the method described in the International Council on Pesticide Analysis (CIPAC), the entire contents of which are incorporated herein by reference. ) MT192-Viscosity of liquids by rotational viscometer may be used. If viscosity is stated in the subject application, the viscosity was measured using spindle 62 at 12 rpm. or measured with a CIPAC MT192 using spindle 63 at 12 rpm will be done.

[0121] In some embodiments, the viscosity is measured using spindle 62 at 12 rpm. In an embodiment, the viscosity is measured using spindle 63 at 12 rpm. So, use spindle 62 at 12 rpm or use spindle 63 at 12 rpm The composition has a viscosity of at least 500 cP as measured using a CIPAC MT192. In some embodiments, the spindle 62 is operated at 12 rpm or When measured using a CIPAC MT192 with spindle 63 at 2000 pm, the composition In some embodiments, the viscosity is between 500 cP and 3000 cP. CIPAC MT19 with spindle 62 or CIPAC MT19 with spindle 63 at 12 rpm When measured using a viscosity measuring device, the composition has a viscosity of 500 cP to 2500 cP. In the embodiment, spindle 62 is used at 12 rpm or spindle 63 is used at 12 rpm. When measured using a CIPAC MT192 using In some embodiments, the viscosity is 0 cP using spindle 62 at 12 rpm. When measured using a CIPAC MT192 with spindle 63 at 12 rpm or In some embodiments, the composition has a viscosity of 1600 cP to 2200 cP. pm using spindle 62 or 12 rpm using spindle 63 CIPA The composition has a viscosity of less than or equal to 3000 cP as measured using a CMT192.

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

[0123] In some embodiments, the total amount of aqueous carrier in the SC composition is about 3% by weight based on the total weight of the composition. In some embodiments, the total amount of aqueous carrier in the SC composition ranges from 0% to about 70% by weight. In some embodiments, the range is from about 40% to about 60% by weight based on the total weight of the composition. The total amount of the aqueous carrier in the SC composition is about 40% to about 50% by weight based on the total weight of the composition. The range is.

[0124] In some embodiments, the total amount of aqueous carrier in the SE composition is about 3% 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 0% to about 70% by weight. In some embodiments, the range is from about 40% to about 60% by weight based on the total weight of the composition. The total amount of the aqueous carrier in the SE composition is about 40% to about 50% by weight based on the total weight of the composition. The range is.

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

[0126] In some embodiments, the total amount of non-aqueous carrier in the OD composition is about 100% by weight of the total composition. In some embodiments, the non-aqueous carrier in the OD composition ranges from 30% to about 80% by weight. The total amount ranges from about 40% to about 70% by weight, based on the total weight of the composition. In the OD composition, the total amount of the non-aqueous carrier is about 50% by weight based on the total weight of the composition. .

[0127] In some embodiments, the total amount of non-aqueous carrier in the EC composition is about In some embodiments, the non-aqueous carrier in the EC composition is in the range of 30% to about 80% by weight. The total amount ranges from about 40% to about 70% by weight, based on the total weight of the composition. The total amount of the non-aqueous carrier in the EC composition is about 40% to about 80% by weight based on the total weight of the composition. In some embodiments, the total amount of non-aqueous carrier in the EC composition is in the range of 100% by weight of the composition. It accounts for approximately 80% by weight of the total weight.

[0128] In some embodiments, the concentration of the compound of formula I in the stable liquid composition is from 150 g / L to 75 In some embodiments, the concentration of the compound of formula I in the stable liquid composition is 30.0 g / L. In some embodiments, the concentration of the compound of formula I in the stable liquid composition is 0 g / L to 750 g / L. In some embodiments, the concentration of the compound of formula I in the stable liquid composition is 450 g / L. The concentration of the substance is 660g / L.

[0129] In some embodiments, the concentration of the compound of formula I in the composition is about 100% by weight of the total composition. In some embodiments, the concentration of the compound of formula I in the composition is greater than 5% by weight. In some embodiments, the compound of formula I in the composition is more than 10% by weight based on the total weight of the composition. In some embodiments, the concentration of the compound is greater than 25% by weight based on the total weight of the stable composition. The concentration of the compound of formula I in the composition is more than 50% by weight based on the total weight of the stable liquid composition. do.

[0130] In some embodiments, the concentration of the compound of formula I in the SC composition is about 100% by weight of the total composition. In some embodiments, the concentration of the compound of formula I in the SC composition is greater than 25% by weight. , more than 50% by weight based on the total weight of the stable liquid composition.

[0131] In some embodiments, the concentration of the compound of formula I in the SE composition is about 100% by weight of the total composition. In some embodiments, the concentration of the compound of formula I in the SE composition is greater than 25% by weight. , more than 50% by weight based on the total weight of the stable liquid composition.

[0132] In some embodiments, the concentration of the compound of formula I in the OD composition is about 100% by weight of the total composition. In some embodiments, the concentration of the compound of formula I in the OD composition is greater than 25% by weight. , more than 50% by weight based on the total weight of the stable liquid composition.

[0133] In some embodiments, the concentration of the compound of formula I in the EC composition is about 100% by weight of the stable liquid composition. In some embodiments, the concentration of the compound of formula I in the EC composition is greater than 5% by weight. is greater than 10% by weight based on the total weight of the stable liquid composition. The concentration of the compound of formula I in the composition is more than 25% by weight based on the total weight of the stable liquid composition. do.

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

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

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

[0137] In some embodiments, the composition comprising a non-aqueous carrier comprises dimethyl sulfoxide (DMSO). Does not include.

[0138] In some embodiments, compositions comprising a non-aqueous carrier do not include morpholine.

[0139] In some embodiments, compositions comprising a non-aqueous carrier do not include N-methylpyrrolidone.

[0140] The present invention relates to (a) a fungicidally effective amount of a compound of formula I:

[0141] [ka] (b) an aqueous liquid carrier, and (c) at least one stabilizing surfactant A stable concentrated suspension (SC) composition having a pH in the range of 5 to 7.5. The composition is provided as described above.

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

[0143] [ka] (b) an aqueous liquid carrier, and (c) at least one stabilizing surfactant A suspoemulsion (SE) composition comprising: The above composition is provided.

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

[0145] [ka] (b) a non-aqueous liquid carrier, and (c) at least one stabilizing surfactant An oil dispersion (OD) composition comprising: and / or the viscosity of the composition is at least 500 cP. The composition is provided as described above.

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

[0147] [ka] (b) a non-aqueous liquid carrier, and (c) at least one stabilizing surfactant An emulsion (EC) composition comprising: The composition has less than .5% by weight.

[0148] In some embodiments, a 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 may be in the form of, but not limited to, amorphous, crystalline, solvated or hydrated forms. "Solvates" refers to any solid form, including solvates.

[0150] Compounds of formula I include crystalline forms of compounds of formula I.

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

[0152] Polymorphs of the compound of formula I are disclosed in PCT International Publication No. WO 2005 / 023331, the entire contents of which are incorporated herein by reference. This is described in Patent Publication No. 2019 / 038583 (published on February 28, 2019).

[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 is 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) has an average molecular weight of 9.08, 10.98, 14.0 5, 17.51, 18.75, 21.63, 23.33, 24.70, 24.83, 25 The X-ray powder diffraction pattern showed characteristic peaks at 2θ angles of 0.37, 26·51, and 29·23. In one embodiment, the powder X-ray diffraction pattern of Form I exhibits 14.05, 17.5 It includes characteristic peaks at 2θ angles of 1, 18.75, 21.63 and 26.51. In the powder X-ray diffraction pattern of Form I, the peaks are 14.05, 17.51, 18.75 and It contains a characteristic peak at a 2θ angle of 21.63.

[0156] In some embodiments, the crystalline polymorphic form (Form I) exhibits decomposition that begins at temperatures above 210° C. It is characterized by:

[0157] In some embodiments, the crystalline polymorphic form (Form I) has a peak temperature of about 160° C. A dominant endothermic peak with an onset temperature of about 159° C. and a Differential scanning calorimetry characterized by a dominant endothermic peak with a fusion enthalpy of 1000 / g The measured (DSC) thermogram is shown.

[0158] In one embodiment, the crystalline polymorphic form (Form II) has an average molecular weight of 7.98, 9.20, 9.96, 1 1.88, 15.99, 18.49, 21.23, 22.33, 22.59, 26.73 In one embodiment, Form I exhibits an X-ray powder diffraction pattern having characteristic peaks at 2θ angles of 0.01 to 0.05. The powder X-ray diffraction pattern of I is 9.20, 9.96, 11.88, 22.33 and 22 In one embodiment, the powder X-ray diffraction pattern of Form II includes a characteristic peak at a 2θ angle of 0.59. The spectrum contains characteristic peaks at 2θ angles of 9.20, 11.88, 22.33, and 22.59. nothing.

[0159] In one embodiment, the crystalline polymorphic form (Form II) is subject to decomposition starting at temperatures above 210° C. TG-FTIR thermograms characterized by the above.

[0160] In one embodiment, the crystalline polymorphic form (Form II) has a predominant peak temperature of about 157° C. A dominant endothermic peak with an onset temperature of about 156° C. and a thermal energy of about 112 J / Differential scanning calorimetry characterized by a dominant endothermic peak with a fusion enthalpy of g The differential scanning calorimetry (DSC) thermogram is shown.

[0161] In one embodiment, the crystalline hydrate form (hydrate) has a viscosity of 5.34, 7.48, 10.68, 16.05, 21.79, 22.99, 23.19, 24.95, 26.95, 27.6 The X-ray powder diffraction pattern has a characteristic peak at a 2θ angle of 3. The powder X-ray diffraction pattern of the product was 5.34, 7.48, 10.68, 16.05 and 21 In one embodiment, the powder X-ray diffraction pattern of the hydrate comprises a characteristic peak at a 2θ angle of .79. contains characteristic peaks at 2θ angles of 5.34, 7.48, 10.68 and 16.05.

[0162] In one embodiment, the crystalline hydrate form (hydrate) is subject to decomposition beginning at temperatures above 190° C. TG-FTIR thermograms characterized by the above.

[0163] In one embodiment, the crystalline hydrate form (hydrate) has a peak temperature of about 139.5° C. A dominant endothermic peak with an onset temperature of about 139° C., and a dominant endothermic peak with an onset temperature of about 115° C. A differential scanning calorimeter characterized by a dominant endothermic peak with an enthalpy of fusion of J / g Quantitative (DSC) thermograms are shown, where the DSC is measured in a sealed dish.

[0164] In one embodiment, the crystalline hydrate form (hydrate) is a predominantly crystalline hydrate having a peak temperature of about 160° C. A dominant endothermic peak with an onset temperature of about 159° C. and a thermal energy of about 98 J / g Differential scanning calorimetry characterized by a dominant endothermic peak with a fusion enthalpy of (DSC) thermograms are shown, where the DSC is measured in an open pan.

[0165] In one embodiment, the crystalline solvate form (form S5) has a viscosity of 5.42, 7.50, 10.0 6, 10.82, 12.80, 16.91, 21.55, 23.13, 24.83, 26 The X-ray powder diffraction pattern shows characteristic peaks at 2θ angles of 0.81 and 27.77. In an embodiment, the powder X-ray diffraction pattern of Form S5 is 5.42, 7.50, 10.06, 1 In one embodiment, Form S5 contains characteristic peaks at 2θ angles of 0.82 and 16.91. The powder X-ray diffraction pattern shows 2θ angles of 5.42, 7.50, 10.82 and 16.91. Contains characteristic peaks.

[0166] In one embodiment, the crystalline solvate form (form S5) has an onset temperature of greater than 180° C. TG-FTIR thermograms characterized by the solutions are shown.

[0167] In one embodiment, the crystalline solvate form (form S8) has a viscosity of 4.7, 5.00, 5.38, Specially for 2θ angles of 6.26, 9.66, 15.93, 21.05, 23.97, and 24.69 The X-ray powder diffraction pattern, as shown in FIG. The powder X-ray diffraction pattern for Form S8 is 4.7, 5.00, 5.38, 6.26, 9.66 and 23.97 2θ angles. In one embodiment, Form S8 has a powder X-ray diffraction pattern. The diffraction pattern shows characteristic peaks at 2θ angles of 4.7, 5.00, 9.66 and 23.97. Includes.

[0168] In one embodiment, the crystalline solvate form (form S8) has an onset temperature of greater than 180° C. TG-FTIR thermograms characterized by the solutions are shown.

[0169] In one embodiment, the crystalline solvate form (Form S1) has a viscosity of 5.34, 7.48, 10.1 0, 10.68, 12.90, 16.07, 21.83, 23.09, 24.91, 26 The compound exhibits an X-ray powder diffraction pattern having a characteristic peak at a 2θ angle of .93. The powder X-ray diffraction pattern of Form S1 has 2θ angles of 5.34, 7.48 and 10.68. In one embodiment, the powder X-ray diffraction pattern of Form S1 comprises characteristic peaks of 5.34, 7. In one embodiment, the compound includes characteristic peaks at 2θ angles of 0.48, 10.68, and 21.83. The powder X-ray diffraction pattern of Form S1 is 5.34, 7.48, 10.68, 16.07 and and characteristic peaks at 2θ angles of 21.83.

[0170] In one embodiment, the crystalline solvate form (Form S1) has an onset temperature of greater than 200° C. TG-FTIR thermograms characterized by the solutions are shown.

[0171] In some embodiments, the compound of formula I is a mixture of the compound of formula I in crystalline form.

[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 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 At least 75% of the crystal form is 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% of the crystalline form I.

[0175] In some embodiments, the mixture is a mixture of crystalline Form II and a 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. The material is at least 75% crystalline Form II.

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

[0177] In some embodiments, the composition comprises a non-ionic stabilizing surfactant. In some embodiments, the composition comprises an anionic stabilizing surfactant. It includes a combination of an ionic and an anionic stabilizing surfactant.

[0178] In some embodiments, the concentrated suspension (SC) composition comprises at least one stabilizing surfactant. In some embodiments, the concentrated suspension (SC) composition comprises at least two stabilizing agents. In some embodiments, the concentrated suspension (SC) composition comprises two stabilizing domains. Contains surfactant.

[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. Composition E contains 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 is a compound of formula I in a liquid carrier. Reduces the rate of crystal growth. 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 non-ionic stabilizing surfactant. In some embodiments, the non-ionic stabilizing surfactant is a polymeric, alkoxylated amine. esters of alkoxylated diethylethanolamine; esters of polyalkylene amines; The carboxylic acid ether is selected from the group consisting of an alkoxy alcohol ether, and an alcohol.

[0183] In some embodiments, the polymer is a block polymer of a random polymer. In some embodiments, the polymer is a triblock polymer. The block polymer is an ABA block polymer. In some embodiments, the polymer is , low HLB (hydrophile-lipophile balance) value, In some embodiments, the polymer has an HLB value of Atlox™ 491. 2 (manufactured and sold by Croda).

[0184] In some embodiments, the non-ionic stabilizing surfactant is an ester of an alkoxylated amine. In some embodiments, the ester of the alkoxylated amine is Atlox (trademark). ) 4915 (manufactured and sold by Croda). The non-ionic stabilizing surfactant was Atlox® 4915 (manufactured by Croda). In some embodiments, the non-ionic stabilizing surfactant is In some embodiments, the non-ionic stabilizer is an alkoxylated diethylethanolamine. In some embodiments, the hydroxyl surfactant is diethylethanolamine monotrimerate. The non-ionic stabilizing surfactant was Altox® 4915 (manufactured by Croda). (manufactured and sold by the U.S. Department of Transportation)

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

[0186] In some embodiments, the non-ionic stabilizing surfactant is an alkoxylated fatty alcohol. It is.

[0187] In some embodiments, the alkoxylated fatty alcohol is Genapol® X080 (manufactured and sold by Clariant), Genapol (registered Trademark) X050 (manufactured and sold by Clariant), tridecyl aryl Cholesterol polyglycol ether, Rhodasurf® LA30 (Solva (manufactured and sold by Aerosol Corporation), Aerosol (registered trademark) OT-SE or A erosol(R) 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 (registered trademark) BR (manufactured and sold by Solvay) (That is.)

[0188] In some embodiments, the alkoxylated fatty alcohol is Genapol® X080 (manufactured and sold by Clariant), Genapol (registered Trademark) X050 (manufactured and sold by Clariant), tridecyl aryl Cholesterol polyglycol ether, or Rhodasurf® LA30 (So (manufactured and sold by Lvay)

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

[0190] In some embodiments, the alcohol has a short carbon chain of C1 to C6. In the case of alcohols, the alcohols have long carbon chains of C7 to C20.

[0191] In some embodiments, the non-ionic stabilizing surfactant is a polyalkylene oxide polya It is a non-ionic derivative of aryl ether.

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

[0193] In some embodiments, the ionic stabilizing surfactant is Aerosol® OT -SE or Aerosol® OT-100 (manufactured by Solvay and (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. Anionic stabilizing surfactants contain anionic groups such as phosphonates and sulfonates. An example of an ionic surfactant that can be used is Aerosol® Dioctyl sulfosuccinate, manufactured and sold by Solvay as OT-SE The compound is sodium phosphate.

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

[0196] In some embodiments, the composition comprises at least one non-ionic 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. Contains surfactant.

[0197] In some embodiments, a non-ionic stabilizing surfactant and an anionic stabilizing surfactant are used. In some embodiments, the composition comprises a non-ionic stabilizing surfactant and and an anionic stabilizing surfactant is an SE composition.

[0198] In some embodiments, one of the stabilizing surfactants is a polyalkylene oxide polyaryl In some embodiments, the polyalkylene oxide polyaryl ether derivatives are The ether derivatives are non-ionic derivatives of polyalkylene oxide polyaryl ethers. In some embodiments, the polyalkylene oxide polyaryl ether surfactant are anionic derivatives of polyalkylene oxide polyaryl ethers.

[0199] In some embodiments, the composition comprises at least two stabilizing surfactants. In an embodiment, the two stabilizing surfactants are polyalkylene oxide polyaryl ethers. In some embodiments, the two stabilizing surfactants include derivatives of polyalkylene. Nonionic derivatives of polyaryl ethers and polyalkylene oxides Includes anionic derivatives of aryl ethers.

[0200] In some embodiments, the non-ionic derivatives of polyalkylene oxide polyaryl ethers The entities are compounds having an aryl group substituted with at least two aromatic groups.

[0201] In some embodiments, the non-ionic derivatives of polyalkylene oxide polyaryl ethers The body has the following structures:

[0202] [ka] has.

[0203] In some embodiments, the non-ionic derivatives of polyalkylene oxide polyaryl ethers The body has the following structures:

[0204] [ka] has.

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

[0206] In some embodiments, anionic derivatives of polyalkylene oxide polyaryl ethers is phosphate (PO 4 ), phosphonates (PO 3 ), sulfonates (SO 3 ) and Sulfate (SO 4 In some embodiments, the polya The anionic group of the anionic derivative of alkylene oxide polyaryl ether is phosphate. (PO 4 ), phosphonates (PO3 ), sulfonates (SO 3 ) and sulfate (S O 4 ) an anionic group selected from

[0207] In some embodiments, the polyalkylene oxide polyaryl ether is polyethylene Oxide groups, polypropylene oxide, polybutylene oxide and any combination thereof In some embodiments, the polyalkylene oxide group is selected from the group consisting of The alkylene oxide group is polyethylene oxide. In some embodiments, the polyalkylene oxide group is The xylene oxide group is polypropylene oxide.

[0208] Polyalkylene oxides include, but are not limited to, copolymers and homopolymers. Copolymers may include, but are not limited to, random polymers and block polymers. In some embodiments, the polyalkylene oxide group may include a dibromoalkylene oxide polymer. In some embodiments, the polyalkylene oxide group is a triblock copolymer. It is a copolymer.

[0209] In some embodiments, the polyalkylene oxide polyaryl ether is In some embodiments, the polyalkylene oxide is a styryl phenyl ether. The silyl polyaryl ether is a polyalkylene oxide benzyl phenyl ether. In some embodiments, the polyalkylene oxide polyaryl ether is In some embodiments, the polyalkylene oxide is a polyalkylene oxide bisphenyl ether. The polyaryl ether is a polyalkylene oxide tristyryl phenyl ether. In some embodiments, the polyalkylene oxide polyaryl ether is In some embodiments, the polyalkylene oxide is distyryl phenyl ether. Polyoxyethylene distyryl phenyl ether is a It is.

[0210] In some embodiments, the polyalkylene oxide polyaryl ether is anionically stabilized. Anionic stabilizing surfactants include phosphonates and sulfonates. This refers to a compound having an anionic group.

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

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

[0213] [ka] has.

[0214] In some embodiments, anionic derivatives of polyalkylene oxide polyaryl ethers is a tristyrylphenol ethoxylate phosphate ester.

[0215] In some embodiments, the polyalkylene oxide polyaryl ether is a tristyryl Phenol ethoxylate phosphate ester. Preferably, tristyrylphenol Ethoxylate phosphate esters are a class of esters manufactured and sold by Solvay. The product is oprophor® 3D33.

[0216] In some embodiments, the polyalkylene oxide polyaryl ether has 54EO. 2,4,6-tri-(1-phenylethyl)phenol polyglycol ether Preferably, 2,4,6-tri-(1-phenylethyl)phenol having 54EO is used. Polyglycol Ether is an EPO manufactured and sold by Clariant. mulsogen(registered trademark) TS540.

[0217] In some embodiments, the polyalkylene oxide polyaryl ether is an ethoxylated Preferably, the ethoxylated tristyrylphenol is Soprophor® TS / 5 manufactured and sold by Solvay The answer is 4.

[0218] In some embodiments, the salt is sodium, potassium, ammonium, calcium, magnesium At least one cation selected from the group consisting of nesium and combinations thereof. nothing.

[0219] Polyalkylene oxide polyaryl ether surfactants include, but are not limited to, , polyphenylethylphenol and tristyrylphenol.

[0220] Polyalkylene oxide polyaryl ether surfactants include, but are not limited to, , non-capped surfactants, end-capped surfactants, or combinations thereof. Good too.

[0221] In some embodiments, the composition comprises a combination of stabilizing surfactants, The combination is a nonionic polyalkylene oxide polyaryl ether surfactant and an anionic Some examples include mixtures of aryl ether and polyalkylene oxide surfactants. In an embodiment, the non-ionic surfactant is tristyrylphenol ethoxylate. In some embodiments, the anionic surfactant is a tristyrylphenol ethoxylate phosphatase. It is an ether.

[0222] In some embodiments, the stabilizing surfactant combination is tristyrylphenol ethoxylate. phosphate ether and tristyrylphenol ethoxylate phosphate ether.

[0223] In some embodiments, the nonionic polyalkylene oxide polyaryl ether is It 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 embodiments, the polyalkylene oxide group is polyoxypropylene. In one embodiment, the polyalkylene oxide group is a block copolymer of polyoxyethylene. In some embodiments, the polyalkylene oxide group is a block of polyoxypropylene. It is a copolymer.

[0225] Polyalkylene oxides include, but are not limited to, polyethoxylated groups, polypro The copolymer may include polyoxylated groups, polybutoxylated groups, and any combination thereof.

[0226] Polyalkylene oxides include, but are not limited to, copolymers and homopolymers. may include:

[0227] Copolymers include, but are not limited to, random polymers and block polymers. It may include.

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

[0229] In some embodiments, the polyalkylene oxide polyaryl ether is In some embodiments, the polyalkylene oxide is distyryl phenyl ether. Polyoxyethylene distyryl phenyl ether is a It is.

[0230] In some embodiments, the non-ionic derivatives of polyalkylene oxide polyaryl ethers The body is a tristyrylphenol ethoxylate phosphate ester.

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

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

[0233] In some embodiments, the stabilizing surfactant is tristyrylphenol polyethylene glycol. It is a non-ionic derivative of cholesteryl ether.

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

[0235] In some embodiments, the composition comprises two stabilizing surfactants, and both stabilizing surfactants In some embodiments, the agent is a derivative of a polyalkylene oxide polyaryl ether. The composition comprises two stabilizing surfactants, one of which is a polyalkylene olefin. A stabilizing surfactant is a nonionic derivative of an oxide polyaryl ether. It is an anionic derivative of an alkylene oxide polyaryl ether.

[0236] In some embodiments, the composition comprises 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 a polyalkylene oxide polyaryl It is an anionic derivative of ether.

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

[0238] In some embodiments, the SC composition comprises two stabilizing surfactants, and both stabilizing surfactants The activator is a derivative of a polyalkylene oxide polyaryl ether. In one embodiment, the composition comprises two stabilizing surfactants, one of which is a polyalkylene. A stabilizing surfactant is a nonionic derivative of polyoxyethylene oxide polyaryl ether. It is an anionic derivative of real alkylene oxide polyaryl ether.

[0239] In some embodiments, the SC composition comprises at least two stabilizing surfactants, At least one stabilizing surfactant is a non-isopropyl ether of polyalkylene oxide polyaryl ether. The at least one stabilizing surfactant is a polyalkylene oxide polyionic derivative. It is an anionic derivative of triaryl ether.

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

[0241] In some embodiments, the SE composition comprises two stabilizing surfactants, and both stabilizing surfactants The activator is a derivative of a polyalkylene oxide polyaryl ether. In one embodiment, the composition comprises two stabilizing surfactants, one of which is a polyalkylene. A stabilizing surfactant is a nonionic derivative of polyoxyethylene oxide polyaryl ether. It is an anionic derivative of real alkylene oxide polyaryl ether.

[0242] In some embodiments, the SE composition comprises at least two stabilizing surfactants, At least one stabilizing surfactant is a non-isopropyl ether of polyalkylene oxide polyaryl ether. The at least one stabilizing surfactant is a polyalkylene oxide polyionic derivative. It is an anionic derivative of triaryl ether.

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

[0244] In some embodiments, the stabilizing surfactant is tristyrylphenol ethoxylate phosphorus. It is an acid ester.

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

[0246] In some embodiments, the polyalkylene oxide polyaryl ether is Claria The antibody was Emulsogen (registered trademark) TS540 manufactured by nt.

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

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

[0249] Polyaryls include, but are not limited to, polyphenylethylphenols and triphenylphenylphenols. It may refer to styrylphenol.

[0250] Polyalkylene oxide polyaryl ether surfactants are non-capped surfactants , end-capped surfactants, or combinations thereof.

[0251] In some embodiments, the surfactant combination comprises a non-ionic polyalkylene oxide poly Aryl ether surfactants and the anionic polyalkylene oxide polyaryl ether world. In some embodiments, the non-ionic surfactant is a mixture of tristilbene and a surfactant. In some embodiments, the anionic surfactant is a triphenylphenol ethoxylate. It is a styrylphenol ethoxylate phosphate ether.

[0252] In some embodiments, the surfactant combination comprises a tristyrylphenol ethoxylate and tristyrylphenol ethoxylate phosphate ether.

[0253] In some embodiments, the nonionic polyalkylene oxide polyaryl ether is It 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 embodiments, the polyalkylene oxide group is polyoxypropylene. In one embodiment, the polyalkylene oxide group is a block copolymer of polyoxyethylene. In some embodiments, the polyalkylene oxide group is a block of polyoxypropylene. It is a copolymer.

[0255] Polyalkylene oxides include, but are not limited to, polyethoxylated groups, polypro The copolymer may include polyoxylated groups, polybutoxylated groups, and any combination thereof.

[0256] Polyalkylene oxides include, but are not limited to, copolymers and homopolymers. may include:

[0257] Copolymers include, but are not limited to, random polymers and block polymers. It may include.

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

[0259] In some embodiments, the polyalkylene oxide polyaryl ether is In some embodiments, the polyalkylene oxide is distyryl phenyl ether. Polyoxyethylene distyryl phenyl ether is a It is.

[0260] In some embodiments, the non-ionic derivatives of polyalkylene oxide polyaryl ethers The body is a tristyrylphenol ethoxylate phosphate ester.

[0261] In some embodiments, the stabilizing surfactant is Emulsogen® TS54 The value is 0.

[0262] In some embodiments, the non-ionic derivative of the surfactant is Emulsogen®. The model is TS540.

[0263] In some embodiments, the stabilizing surfactant is Soprophor® TS / 5 The answer is 4.

[0264] In some embodiments, the non-ionic derivatives of polyalkylene oxide polyaryl ethers The agent is Soprophor® TS / 54.

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

[0266] In some embodiments, the stabilizing surfactant is tristyrylphenol polyethylene glycol. It is a non-ionic derivative of cholesteryl ether.

[0267] In some embodiments, the composition comprises a stabilization system.

[0268] In some embodiments, the non-ionic derivatives of polyalkylene oxide polyaryl ethers The weight ratio of the copolymer to the anionic derivative of polyalkylene oxide polyaryl ether is 0. In some embodiments, the polyalkylene oxide polyaryl ether is in the range of 25:1 to 1:1. Nonionic derivatives of polyaryl ethers and aniline derivatives of polyalkylene oxide polyaryl ethers. The weight ratio of the ion derivative is in the range of 0.25:1 to 0.5:1. , nonionic derivatives of polyalkylene oxide polyaryl ethers and polyalkylene oxides The weight ratio of the oxide polyaryl ether to the anionic derivative is about 0.36:1.

[0269] In some embodiments, the stable composition comprises at least 0.5% by weight of the total composition. % of a polyalkylene oxide polyaryl ether stabilizing surfactant. In the form, the stable composition contains from 0.5% to 7% by weight of polyalcohol based on the total weight of the composition. In some embodiments, the stabilizing surfactant is an alkylene oxide polyaryl ether. The composition contains 0.5% by weight to 15% by weight of polyalkylene oxide based on the total weight of the composition. In some embodiments, the stabilized composition comprises a silyl polyaryl ether stabilizing surfactant. The polyalkylene oxide polyamide is present in an amount of 0.5% by weight to 25% by weight based on the total weight of the composition. Contains a aryl ether stabilizing surfactant.

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

[0271] In some embodiments, the stabilizing surfactant is a liquid composition in which the compound of formula I is soluble. In comparison, it is effective in improving the stability of the compounds of formula I in the compositions described herein. In some embodiments, the stability is chemical stability. In some embodiments, the stability is Physical stability.

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

[0273] In some embodiments, the pH adjusting agent may include, but is not limited to, a buffer, a base and / or Alternatively, it may contain an acidifying agent.

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

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

[0276] In some embodiments, the pH adjusting agent is a buffering agent.

[0277] A buffer refers to a combination of an acid and a base. Acids include, but are not limited to, organic acids and Bases include, but are not limited to, organic bases and inorganic bases.

[0278] Organic acids include, but are not limited to, citric acid, formic acid, acetic acid, propionic acid, butyric acid, Examples of suitable carboxylic acids include oxalic acid, lactic acid, malic acid, and benzoic acid.

[0279] Inorganic acids include, but are not limited to, hydrochloric acid, nitric acid, phosphoric acid, sulfuric acid, and boric acid. Some examples include:

[0280] 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 dihydrogen phosphate.

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

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

[0284] In some embodiments, the buffering agent is potassium dihydrogen orthophosphate. So, the concentration of potassium dihydrogen orthophosphate in the stable liquid composition is 1g / L to 5g / L. In some embodiments, the concentration of potassium dihydrogen orthophosphate in the stable liquid composition is In some embodiments, the di-orthophosphate in the stable liquid composition is 1 g / L to 3 g / L. The concentration of potassium hydrogen is approximately 1.7 g / L.

[0285] In some embodiments, the buffering agent is disodium phosphate anhydrous. The concentration of disodium phosphate anhydrous in the stable liquid composition is 1 g / L to 10 g / L. In some embodiments, the concentration of disodium phosphate anhydrous in the stable liquid composition is 5 g / L to In some embodiments, the stable liquid composition contains disodium phosphate anhydrous. In some embodiments, the concentration of anhydrous lysine in the stable liquid composition is 5 g / L to 8 g / L. The concentration of disodium phosphate is approximately 6.9 g / L.

[0286] (iv) A suitable non-aqueous liquid carrier 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. The 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 depends on the polarity of the solvent. The polarity of the solvent is 25 to 50 (whereas water is 100). The solvent (non-aqueous liquid carrier) is Solvent combinations may be used when the polarity of the solvent combination is between 25 and 50. In some embodiments, the solubility of water in the solvent is less than 25 g / L at 20° C. The dipole (D) is less than 10, preferably less than 5. In some embodiments, the solvent has a dipole (D) of less than 1 It has a Log P value of > .

[0291] In some embodiments, the non-aqueous carrier is an aromatic hydrocarbon, a paraffin, a petroleum oil, a diesel , mineral oils, esters and / or amides of fatty acids, tall oil fatty acids, and any combination thereof. Any combination of the above is selected from the group consisting of:

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

[0293] In some embodiments, the aromatic hydrocarbon is toluene, o-xylene, m-xylene, p -Xylene, ethylbenzene, isopropylbenzene, tert-butylbenzene, naphtha and mono- or poly-alkyl-substituted naphthalenes.

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

[0295] In some embodiments, the non-aqueous liquid carrier is a vegetable oil. , 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, flax It is selected from the group consisting of kernel 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. The alkyl ester of a fatty acid is a C18 methyl canola oil ester. 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. Amides of fatty acids are C 1 ~C 3 Amines, alkylamines and alkanolamines (C 6 ~ C 18 having a carboxylic acid.

[0298] In some embodiments, the non-aqueous carrier is an alkyl ester of a fatty acid. In the present embodiment, alkyl esters of fatty acids include methyl oleate and ethyl oleate. C 8 ~C 22 C in fatty acids 1 ~C 4 The monohydric alcohol ester is selected from the group consisting of monohydric alcohol esters.

[0299] Other examples of non-aqueous carriers are methyl fatty acid esters, vegetable oil alkyl esters, xylene, Octanol, acetophenone, cyclohexanone, Solvesso™ (Exx (manufactured and sold by OnMobil Chemical Company), N-methylpyridine lolidone, tributyl sulfate (TBP), ethylhexyl lactate (EHL), fatty acids (natural or synthetic) alkyl (linear or cyclic) amides, aryl acetates (benzyl acetate), In some embodiments, the non-polyethylene glycol ethers are selected from the group consisting of polyethylene glycol, benzyl acetate, and propylene carbonate. The aqueous carrier is cyclohexanone. In some embodiments, the non-aqueous carrier is acetophenone. In some embodiments, the non-aqueous carrier is benzyl acetate. The non-aqueous carrier is propylene carbonate.

[0300] (v) Other additives The compositions of the present invention may include, but are not limited to, a solid diluent, a liquid diluent, a wetting agent, an adhesive, agents, thickeners, defoamers, preservatives, humectants, antioxidants, binders, fertilizers, or antifreeze agents. In addition, one or more additional agriculturally acceptable inert additives known in the art may be added. In addition, the composition may contain additional crop protection agents known in the art. , for example insecticides, safeners, agents for controlling phytopathogenic fungi or bacteria, etc. It may further include.

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

[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 composition Bentone SD-1 or Bentone SD-3 The amount is between 0.5 and 1.0 wt.%. In some embodiments, the rheology modifier is Attagel® 50 (manufactured by BASF) and Benton e SD-1. In some embodiments, the composition contains Attagel (registered trademark). The amount of Bentone SD® 50 in the composition was 0.5% by weight. The amount of -1 is 0.5% by weight. Attagel® 50 (based on the total weight of the composition) 0.5% by weight based on the total weight of the composition and Bentone SD®-1 The use of 0.5% by weight of ethylenediaminetetraacetate reduced the decomposition of the compound of formula I by 7-8% after storage for 8 weeks at 40°C. The water concentration of the composition was reduced from 0.01 to 4%. Bentone S was used as a rheology modifier. It should be kept below 0.5%, including when D®-1 is used.

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

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

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

[0306] In some embodiments, the thickening agent is Aerosil® 200, Aerosil (registered trademark) R972, Aerosil (registered trademark) R202 and any combination thereof The compound is selected from the group consisting of:

[0307] In some embodiments, the silica thickener is Aerosil® R202, Aerosil® R202, osil® R812, and any combination thereof.

[0308] In some embodiments, the amount of Aerosil® R202 in the composition is In some embodiments, the A in the composition is between 1% and 5% by weight based on the total weight of the composition. The amount of erosil® R202 is from 1.7% to 2% by weight relative to the total weight of the composition. Between 0.5% by weight.

[0309] In some embodiments, the amount of Aerosil® R812 in the composition is In some embodiments, the A in the composition is between 1% and 5% by weight based on the total weight of the composition. The amount of erosil® R812 is from 3.0% to 3.0% by weight based on the total weight of the composition. Between 0.5% by weight.

[0310] In some embodiments, the composition contains Bentone SD®-1 or Ben The amount of Tone SD®-3 is from 0.5 to 1.0 wt. %.

[0311] In some embodiments, the concentration of the rheology modifier in the stable liquid composition is from 1 g / L to 15 g / L. In some embodiments, the concentration of the rheology modifier in the stable liquid composition is In some embodiments, the rheology modification in the stable liquid composition is from 1 g / L to 5 g / L. The concentration of the agent is 2.3 g / L. In some embodiments, the rheology of the stable liquid composition is The concentration of the modifying agent is 0.5 g / L to 130 g / L. In some embodiments, the stable liquid composition The concentration of the rheology modifier in the composition is 3 g / L.

[0312] In some embodiments, the composition further comprises at least one adjuvant. In embodiments, the adjuvant is (i) polyalkylene oxide alkyl ethers, (ii) siloxane polyalkylene oxide copolymers, (iii) esters of fatty acids, (iv) Vinylpyrrolidone and its derivatives, and (v) Sugar surfactants is selected from the group consisting of:

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

[0314] In some embodiments, the compositions of the present invention may contain additional acceptable inert additives. In some embodiments, the agriculturally acceptable inert additive further comprises Inert additives that may be used include, but are not limited to, antioxidants, defoamers, dyes, pigments, flavoring agents, and the like. , dispersants, synergists, encapsulants, light stabilizers, binders, stickers, water-soluble fertilizers, repellents and Refers to the sensitizer.

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

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

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

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

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

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

[0321] In some embodiments, the stable liquid composition further comprises an antioxidant. Examples include, but are not limited to, clay, BHA, BHT, TBH, propyl gallate, chitosan, etc. These include sodium malonate, tocopherol, pyrogallol and epichlorohydrin. do.

[0322] In some embodiments, the stable liquid composition further comprises a defoamer. Examples of suitable materials include, but are not limited to, organosilicon, EO / PO defoamers, and polyacrylic acid acrylates. Kill is one example.

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

[0324] In some embodiments, the stable liquid composition further comprises a humectant. Examples of humectants include , but are not limited to, dialkyl naphthalenesulfonates, dialkyl sulfosuccinates Alkyl, metal salts of alkyl ether sulfonates, alpha olefin sulfates, N-acyl N-alkyl taurates, linear alkylbenzene sulfonates, carboxylic acid esters, sulfate esters, phosphate esters, polyoxyethylene surfactants, ethoxylated Ethoxylated alkylphenols, ethoxylated fatty alcohols, sorbitol anhydride esters and cetyltrimethylammonium bromide.

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

[0326] Surfactants include, but are not limited to, alcohol polyglycol ethers, alkyl End-capped ethoxylated glycol, end-capped alkyl block Alkoxylate glycols, dialkyl sulfosuccinates, phosphate esters, sulfur Alkyl sulfonate, alkylaryl sulfonate, tristyrylphenol alkoxyl esters, natural or synthetic fatty acid alkoxylates, natural or synthetic fatty alcohol alkoxylates Alcohol alkoxylates, alkoxylated alcohols (n-butyl alcohol polyglycol ethers block copolymers (ethylene oxide-propylene oxide block copolymers, etc.) ethylene oxide-butylene oxide block copolymers, etc.) or The combination of

[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 methyl end-capped tridecyl ethoxylate In some embodiments, the adjuvant is a methyl ethylene oxide having six ethylene oxide units. It is an end-capped tridecyl ethoxylate.

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

[0329] In some embodiments, the compositions disclosed herein may include an additional insecticide. .

[0330] The disclosed compositions include at least 1% by weight of one or more of the compositions and another pesticide compound. Such additional insecticidal compounds may optionally include combinations of Compatible with the synergist composition of the present disclosure in the selected vehicle and does not antagonize the action of the compound Fungicides, insecticides, nematicides, acaricides, arthropodicides, bactericides (bactericides) or combinations thereof. In some embodiments, other pesticide compounds of formula I may be used as additional pesticides when using the same or different pesticides. Used as a poison. Insecticidal compounds and synergist compositions are generally in the range of 1:100 to 1: They can be mixed in a weight ratio of 0.00:1.

[0331] Mixtures comprising a compound of formula I and an adjuvant: Adjuvants are inactive substances added to improve the performance of active ingredients and their compositions. The enhanced activity of the compounds of formula I is due to the rapid drift, high drop density on the leaves. Many drawbacks have been observed that dramatically affect and limit penetration into plants, including surface tension. This is particularly difficult.

[0332] Dispensing at least one selected adjuvant together with a compound of formula (I) comprises Enhancement of the efficacy of compounds of formula (I) in controlling fungal attack on plants It has been discovered that the adjuvant of choice can be incorporated into a composition containing a compound of formula I. The adjuvant of choice may also be added to the tank mix containing the compound of Formula I. In addition, when multiple adjuvants are used, the other adjuvants may be added to the tank mix. One or more adjuvants may be incorporated into the composition while in addition to the cox.

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

[0334] [ka] and (b) (i) polyalkylene oxide alkyl ethers, (ii) siloxane polyalkylene oxide copolymers, (iii) esters of fatty acids, (iv) Vinylpyrrolidone and its derivatives, and (v) Sugar surfactants At least one adjuvant selected from the group consisting of The present invention provides a disinfectant mixture comprising:

[0335] In some embodiments, the germicidal mixture is a composition. The item is a tank mix.

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

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

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

[0339] In some embodiments, the alcohol of the polyalkoxylated alcohol is not limited to However, it contains carbohydrate chains of C1 to C26.

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

[0341] Carbohydrate chains include, but are not limited to, saturated chains, unsaturated chains, branched chains and unbranched chains. Can be pointed out.

[0342] In some embodiments, short chain refers to C1-C8. In some embodiments, long chain refers to C9-C It refers to 26.

[0343] In some embodiments, the polyalkylene oxide can be, but is not limited to, polyethylene oxide. polypropylene oxide, polybutylene oxide, or combinations thereof Refers to...

[0344] In some embodiments, the polyalkylene oxide can be, but is not limited to, a copolymer. Copolymers include block copolymers such as polyethylene oxide-polypropylene oxide. copolymers, and / or random copolymers such as ethylene oxide-propylene oxide In some embodiments, the polyalkylene oxide block copolymer is a dialkylene oxide block copolymer. In some embodiments, the polyalkylene oxide block copolymer is The polymer is a triblock copolymer.

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

[0346] In some embodiments, the polyalkylene oxide alkyl ether is an alkyl tail cap. In some embodiments, the alkyl is a short carbohydrate, including but not limited to, Carbohydrate chains include, but are not limited to, saturated chains, unsaturated chains, and long carbohydrate chains. It can refer to saturated chain, branched chain and unbranched chain. In some embodiments, short chain refers to C1-C8. vinegar.

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

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

[0349] In some embodiments, the C16 to C18 alcohol ethoxylate propoxylate esters are Tel is manufactured and sold by Akzo Nobel Agrochemicals. In some embodiments, the C16-C18 arsenic is C16-C18 ethyl ether. Coal ethoxylate propoxylate ether is manufactured and sold by BASF. The product in question is Agnique (registered trademark) BP420.

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

[0351] In some embodiments, the ethoxylated propoxylated alcohol is provided by Croda. The product is Synperonic™ 13 / 9, manufactured and sold by In form, ethoxylated propoxylated alcohol is manufactured and sold by Croda. It is commercially available as Atplus™ PFA.

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

[0353] In some embodiments, the isotridecyl alcohol polyglycol ether is Clar The product is Genapol (registered trademark) X80, manufactured and sold by Iant. In some embodiments, the isotridecyl alcohol polyglycol ether is a polyglycol ether from BASF. The product is manufactured and sold by Trycol®.

[0354] In some embodiments, the polyalkylene oxide alkyl ether may be used to improve the surface tension of the composition. and is effective in improving the diffusion of the compound of formula I on the leaves of plants. This reduction translates into less drift from the leaves.

[0355] In some embodiments, the siloxane polyalkylene oxide copolymer is an organically modified trialkylene oxide copolymer. Refers to siloxane.

[0356] In some embodiments, the siloxane polyalkylene oxide copolymer is from Evonik In some embodiments, the sirolimus is Break-Thru® S233 manufactured by Shiroki Co., Ltd. The polyalkylene oxide copolymer is Silwett ( Registered trademark) 077.

[0357] In some embodiments, the siloxane polyalkylene oxide copolymer is Silicone surfactants are effective in reducing surface tension and providing lipophilic properties. It has been found to be an effective aid in the rapid spreading of the composition across a surface.

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

[0359] In some embodiments, the alkyl ester comprises a carbohydrate chain comprising C10 to C20.

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

[0361] Carbohydrate chains include, but are not limited to, saturated chains, unsaturated chains, branched chains and unbranched chains. Can be pointed out.

[0362] In some embodiments, short chain refers to C1-C8. The ester was Rhodaphac® PA / 23 (ethoxylated) from Solvay. (phosphate esters of methylated fatty alcohols) or Alkamuls (registered trademark) from Solvay Registered Trademark) VO / 2003 (Ethoxylated (18EO) Fatty Acid).

[0363] In some embodiments, the adjuvant is an ethoxylated tridecyl alcohol or a poly Oxyethylene(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, palm oil, rapeseed oil, corn oil, Includes maize oil, soybean oil, palm oil and corn oil.

[0366] In some embodiments, the derivatives of vegetable oils include alkyl esters, polyalkylene oxides, and the like. Refers to...

[0367] Polyalkylene oxides include polyethylene oxide, polypropylene oxide, polybutene, "ethylene oxide" refers to ethylene oxides and combinations thereof.

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

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

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

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

[0372] In some embodiments, the coconut fatty acid esters of polyglycerol ethers are available from Clari. The drug is Synergen (registered trademark) GL5 manufactured and sold by Ant Pharmaceuticals.

[0373] In some embodiments, the esters of fatty acids provide better and more effective penetration of the compounds of formula I. In order to soften the surface properties of the leaves.

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

[0375] In some embodiments, the block copolymer of vinylpyrrolidone and vinyl acetate is As The product is Sokalan (registered trademark) VA64P manufactured and sold by Hland Corporation. do.

[0376] In some embodiments, the block copolymer of vinylpyrrolidone and vinyl acetate is As The material is Agrimer (trademark) VA6 manufactured and sold by Holland.

[0377] In some embodiments, vinylpyrrolidone (PVP) and its derivatives have adhesive and To improve retention characteristics (e.g., rain resistance), the compounds of formula I may be enhanced to adhere to leaves. It is effective for

[0378] Examples of sugar surfactants include, but are not limited to, sorbitan esters, sucrose esters, They may include alkyl polyglycosides, and fatty acid glucamides.

[0379] In some embodiments, the glycosurfactant is an alkyl or fatty acid glucamide. de) derivative.

[0380] In some embodiments, the sugar surfactant is an alkyl glucamide.

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

[0382] In some embodiments, the C8 / C10 fatty acid glucose amide is available from Glariant. and Synergen(R) GA from Sigma-Aldrich.

[0383] In some embodiments, the sugar surfactant is sorbitan and its derivatives.

[0384] In some embodiments, the derivatives of sorbitan include polyethylene oxide derivatives and fats. It is an acid ester.

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

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

[0387] In some embodiments, the sugar surfactant improves the penetration of the compound of Formula I through the leaf surface. This affects the leaf surface to produce

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

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

[0390] In some embodiments, the adjuvants affect penetration in different ways. In terms of form, adjuvants affect penetration in the same manner.

[0391] In some embodiments, the blend of adjuvants includes, but is not limited to, alkyl Combinations of fatty acid esters and fatty alcohol alkoxylates are included. nothing.

[0392] In some embodiments, the alkyl fatty acid ester and the fatty alcohol alkoxylate The combination is Synergen (registered trademark) manufactured and sold by Clariant. (SOC).

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

[0394] In some embodiments, the adjuvant blend may include, but is not limited to, vegetable oils and and / or its derivatives in combination with sugar surfactants.

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

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

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

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

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

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

[0401] In one embodiment, a compound of formula I in a mixture with a polyalkylene oxide alkyl ether. The weight ratio 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: It is 90.

[0403] In one embodiment, the polymerization of vinylpyrrolidone and its derivatives with compounds of formula I in a mixture is The ratio is 1:90.

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

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

[0406] In some embodiments, an adjuvant having a vinylpyrrolidone or derivative structure thereof Weight ratio between the adjuvant having a siloxane polyalkylene oxide copolymer structure and the In some embodiments, vinylpyrrolidone and its derivatives are An adjuvant having a structure of the body and an adjuvant having a siloxane polyalkylene oxide copolymer structure In some embodiments, the weight ratio of the adjuvant to the vinylpyrrolidone is 2:1. Adjuvants having the structure of siloxane polyalkylene oxide copolyol and its derivatives The weight ratio of the adjuvant having a mer structure is 1.4:1.

[0407] In some embodiments, adjuvants having the structure of vinylpyrrolidone and its derivatives and the adjuvant having a polyalkylene oxide alkyl ether structure. In some embodiments, vinylpyrrolidone and its derivatives are Adjuvants having the structure of a steroid and adjuvants having the structure of a polyalkylene oxide alkyl ether The weight ratio of the adjuvant to the formulation is 1:5.5.

[0408] In some embodiments, adjuvants having the structure of vinylpyrrolidone and its derivatives The weight ratio of the adjuvant having a fatty acid ester structure to the adjuvant is in the range of 5:1 to 1:5. In some embodiments, adjuvants having the structure of vinylpyrrolidone and its derivatives are The weight ratio of the adjuvant having a fatty acid ester structure to the adjuvant was 1:3.7.

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

[0410] In some embodiments, adjuvants having the structure of a polyalkylene oxide alkyl ether are Adjuvants containing esters of vanadium and fatty acids and vinylpyrrolidone and its derivatives The weight ratio of the adjuvant having the structure is in the range of 10:5:1 to 1:5:10. In one embodiment, the adjuvant has the structure of a polyalkylene oxide alkyl ether. The structures of the adjuvants having esters of fatty acids and vinylpyrrolidone and its derivatives are shown in Table 1. The weight ratio range of the adjuvant present is 5.7:3.76:1.

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

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

[0415] In some embodiments, the mixtures of the present invention formulated as one composition may include a built-in composition. In some embodiments, the mixture is formulated into two separate compositions, The material is added to the tank mix.

[0416] In some embodiments, the ratio of adjuvant to Compound (I) in the tank mix is ​​50: The time is 1:00~1:50.

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

[0418] In some embodiments, the polyalkylene oxide alkyl ether in the composition / mixture The concentration of the structural adjuvant is at least 3% by weight relative to the total weight of the composition. .

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

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

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

[0422] In some embodiments, the adjuvant in the composition / mixture has the structure of a glycosurfactant. is at least 3% by weight relative to the total weight of the composition.

[0423] In some embodiments, the concentration of polyalkylene oxide alkyl ether in the composition is When the amount is less than 3% by weight based on the total weight of the composition, the polyalkylene oxide alkyl ether Teres are used as surfactants / emulsifiers.

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

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

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

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

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

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

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

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

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

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

[0435] In one embodiment, the polyamine in the mixture or composition of the compound of formula I and the adjuvant is The amount of alkylene oxide alkyl ether is about 1% by weight to about 5% by weight based on the total weight of the composition. The range is % by volume.

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

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

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

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

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

[0441] In one embodiment, the polyalkylene oxide alkyl ether in the composition comprising the compound of formula I The concentration of the terephthalate is 5% by weight relative to the total weight of the composition.

[0442] In one embodiment, the siloxane polyalkylene oxide copolymer in the composition comprising the compound of formula I is The concentration of the polymer is 0.1% by weight relative to 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 The content is 5% by weight based on the total weight of the composition.

[0444] In one embodiment, the concentration of vegetable oils and their derivatives in the composition comprising the compound of formula I is The content is 6% by weight based on the total weight of the composition.

[0445] In one embodiment, the amount of vinylpyrrolidone and its derivatives in the composition comprising the compound of formula I is The concentration is 1.5% by weight relative to the total weight of the composition.

[0446] In one embodiment, the concentration of the sugar surfactant in the composition comprising the compound of formula I is about 100% by weight of the total composition. It is 5% by weight.

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

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

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

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

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

[0452] In one embodiment, the glycoform boundary in the mixture or composition of the compound of formula I and the adjuvant is The amount of surfactant ranges from 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 about 20% by weight of the total composition. 3% by weight. In some embodiments, the concentration of VP / VA in the composition is about 100% by weight of the total composition. It is about 1.5% by weight.

[0454] In some embodiments, the concentration of PVP in the composition is about 0.5 to about 100 parts by weight of the total composition. In some embodiments, the concentration of PVP in the composition is about 1.5% by weight of the total composition. It is about 0.75 to 1.25% by weight.

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

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

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

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

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

[0460] In some embodiments, the adjuvant or multi-adjuvant system / blend is administered as a drop / It affects the surface tension of the composition / diluted composition, acts as a sticking agent, and dissolves the compound of formula I on the leaves. Improves compound diffusion.

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

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

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

[0464] In some embodiments, Agnique® ME 18 RD-F (Fatty Acid, C 16-18 and C18-unsaturated methyl esters) are solvents and built-in adjuvants It is.

[0465] In some embodiments, Genapol® x80 (isotridecyl alcohol) Polyglycol Ether Nonionic Surfactants) are used as emulsifiers / surfactants and built-in It is an adjuvant.

[0466] In some embodiments, Agnique® ME 18 RD-F (Fatty Acid, C 16-18 and C18-unsaturated methyl esters) are the solvent and build-up in OD compositions. It is an adjuvant.

[0467] In some embodiments, Genapol® x80 (isotridecyl alcohol) Polyglycol ether nonionic surfactants) are emulsifiers / surfactants in OD compositions. and built-in adjuvants.

[0468] In some embodiments, the solvent Agnique® ME 18 RD-F (fatty acid , C16-18 and C18-unsaturated methyl esters) are also built-in adjuvants. be.

[0469] In some embodiments, the emulsifier / surfactant Genapol® x80 (Isoto Poly(decyl alcohol polyglycol ether) nonionic surfactants are built-in azide It is also a hubant.

[0470] In some embodiments, the solvent Agnique® ME 18 RD-F (fatty acid , C16-18 and C18-unsaturated methyl esters) are the built-in It is also an adjuvant.

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

[0472] The compositions are prepared according to procedures conventional in the agricultural chemical art, however, the chemicals of this disclosure may be used in combination with other methods. The presence of a mixture of compound (I) and an adjuvant is novel and important.

[0473] Concentrate compositions of the mixtures of the present disclosure may be dispersed in water or another liquid depending on the application. Alternatively, the composition may be in dust or granular form and may be applied without further treatment. or may be diluted before application.

[0474] The compositions most often applied are aqueous suspensions or emulsions. Such water-soluble, water-suspendable, or emulsifiable compositions are usually available as solids or powders known as wettable powders. or liquids commonly known as emulsions, aqueous suspensions, concentrated suspensions or suspoemulsions. The present disclosure provides a method for the preparation of a mixture of glycerol, ... The use of is intended.

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

[0476] In some embodiments, the compositions of the present invention further comprise at least one additional insecticide. In some embodiments, the pesticide is a fungicide, a herbicide, an insecticide, or a nematicide.

[0477] In some embodiments, the compositions of the present invention further comprise at least one additional fungicide. In some embodiments, the disinfectant mixture of the present invention further comprises at least one additional disinfectant. Included.

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

[0479] In some embodiments, the sterol biosynthesis inhibitor is prothioconazole, epoxiconazole. azole, cyproconazole, myclobutanil, prochloraz, metconazole, diphenazole Conazole, tebuconazole, tetraconazole, fenbuconazole, propiconazole le, fluquinconazole, flusilazole, flutriafol, and fenpropimol The compound is selected from the group consisting of

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

[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 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 flutriafol. In some embodiments, the sterol biosynthesis inhibitor is fenpropimorph. In embodiments, the sterol biosynthesis inhibitor is fenpropidin. The sterol biosynthesis inhibitor is ipconazole. In some embodiments, the sterol biosynthesis inhibitor is triticonazole. In some embodiments, the sterol biosynthesis inhibitor is fenhexamid. In some embodiments, the sterol biosynthesis inhibitor is fenpyrazamine. In an embodiment, the sterol biosynthesis inhibitor is fenbuconazole.

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

[0483] In some embodiments, the succinate dehydrogenase inhibitor is benzovindiflupyr, Nthiopyrad, Isopyrazam, Fluxapyroxad, Boscalid, Fluopyram, Vyxa fen, 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. The enzyme inhibitor is penflufen.

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

[0486] In some embodiments, the strobilurin fungicide is azoxystrobin, pyraclostridium sulphate, Robin, picoxystrobin, fluoxastrobin, trifloxystrobin, creso Selected from the group consisting of dimoxystrobin, dimoxystrobin, and orysastrobin .

[0487] In some embodiments, the strobilurin fungicide is azoxystrobin, pyraclostridium sulphate, Robin, picoxystrobin, fluoxastrobin, and trifloxystrobin The compound is selected from the group consisting of:

[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. The fluoxastrobin fungicide is a strobilurin fungicide. The fungicide is trifloxystrobin. In some embodiments, the strobilurin fungicide is kresoxim-methyl. In some embodiments, the strobilurin fungicide is dimoxim-methyl. In some embodiments, the strobilurin fungicide is orysastrobin. be.

[0489] In some embodiments, the at least one additional fungicide is a fungicidal multipoint inhibitor.

[0490] In some embodiments, the bactericidal multipoint inhibitor is mancozeb, chlorothalonil, folpet captan, metiram, maneb, propineb, copper hydroxide, copper octanoate, oxysalt Copper chloride, copper sulfate, copper sulfate (tribasic), man-copper, copper oxine, bis(3-phenylsalicylic acid) Copper thirate, copper zinc chromate, cuprous oxide, copper hydrazinium sulfate, and cuprovain. (cuprobam).

[0491] In some embodiments, the bactericidal multipoint inhibitor is mancozeb. The fungicidal multipoint inhibitor is chlorothalonil. In some embodiments, the fungicidal multipoint inhibitor is In some embodiments, the bactericidal multipoint inhibitor is captan. In embodiments, the bactericidal multipoint inhibitor is metiram. In some embodiments, the bactericidal multipoint inhibitor is propineb. In embodiments of the invention, the bactericidal multipoint inhibitor is copper hydroxide, copper octanoate, copper oxychloride, copper sulfate, Copper sulfate (tribasic), man-copper, copper oxine, copper bis(3-phenylsalicylate), Copper zinc chromate, cuprous oxide, copper hydrazinium sulfate, or cuprobam.

[0492] In some embodiments, the additional fungicide is 2-(thiocyanatomethylthio)-benzothiazolinone. azole, 2-phenylphenol, 8-hydroxyquinoline sulfate, amethoctrazine, Misrubrome, Antimycin, Ampelomyces quisqualis, Aza Conazole, azoxystrobin, Bacillus subtilis, Bacillus subtilis strain QST71 3. Benalaxyl, benomyl, benthiavalicarb isopropyl, benzylaminobenzyl BABS salts, bicarbonates, biphenyls, bismerthiazoles, bitertanols borax, bixafen, blasticidin S, borax, Bordeaux mixture, boscalid, bromocobalamin Nazole, bupirimate, calcium polysulfide, captafol, captan, carbendazim carboxin, carpropamid, carvone, chlazafenone, clozaphenone Roneb, Chlorothalonil, Chlozolinate, Coniothyrium minitans minitans), copper hydroxide, copper octanoate, copper oxychloride, copper sulfate, copper sulfate (tribasic), acid Cuprous chloride, cyazofamid, cyflufenamid, cymoxanil, cyproconazole, Lodinil, Dazomet, Debacarb, Diammonium Ethylenebis(dithiocarbamate) ), dichlofluanid, dichlorophen, diclocymet, diclomedine, dicloran, Diethofencarb, difenoconazole, difenzoquat ion, diflumetrim, Dimethomorph, Dimoxystrobin, Diniconazole, Diniconazole M, Dinobuton , Dinocap, Diphenylamine, Dithianon, Dodemorph, Dodemorph acetate, Dodine, Dodine free base, edifenphos, enestrobin, enestrobulin, epoxyconazo ethanol, ethaboxam, ethoxyquin, etridiazole, famoxadone, phenamide fenarimol, fenbuconazole, fenfuram, fenhexamid, fenoxa nil, fenpiclonil, fenpropidin, fenpropimorph, fenpyrazamine, Fentin, triphenyltin acetate, triphenyltin hydroxide, ferbam, ferimzo Fluazinam, Fludioxonil, Flumorph, Fluopicolide, Fluopyram, Flurolimide, fluoxastrobin, fluquinconazole, flusilazole, frusulf Famid, Flutianil, Flutolanil, Flutriafol, Fluxapyroxad, Fol Fupet, formaldehyde, fosetyl, fosetyl-aluminum, fuberidazole, Laraxyl, furametpyr, guazatine, guazatine acetate, GY-81, hexachloro Benzene, hexaconazole, hymexazole, imazalil, imazalil sulfate, imibe Nconazole, Iminoctadine, Iminoctadine triacetate, Iminoctadine albesilate Salt, iodocarb, ipconazole, ipfenpyrazolone, iprobenfo s, iprodione, iprovalicarb, isoprothiolane, isopyrazam, isotianil , Kasugamycin, Kasugamycin hydrochloride monohydrate, Kresoxim-methyl, Laminarin, Mancopper, mancozeb, mandipropamide, maneb, mefenoxam, mepanipiri Mercuric chloride, mercuric oxide, mercurous chloride, methadone, mepronil, meptyldinocap, Xyl, Metalaxyl M, Metam, Metam Ammonium, Metam Potassium, Metam Sodium metconazole, methasulfocarb, methyl iodide, methyl isothiocyanate, Thiram, metominostrobin, metrafenone, mildiomycin, myclobutanil, na Bam, nitroisopropyl, nuarimol, octilinone, ofurace, oleic acid ( fatty acids), orysastrobin, oxadixyl, oxine copper, oxpoconazole fumarate acid salt, oxycarboxin, pefurazoate, penconazole, pencycuron, penflu Phen, Pentachlorophenol, Pentachlorophenyl Laurate, Penthiopyrad, Phenylmercuric acetate, phosphonic acid, phthalide, picoxystrobin, polyoxin B, poly Oxine, polyoxorim, potassium bicarbonate, hydroxyquinoline sulfate Potassium, probenazole, prochloraz, procymidone, propamocarb, propamoca Rubin hydrochloride, propiconazole, propineb, proquinazid, prothioconazole, pyrazinamide Clostrobin, pyrametostrobin, pyraoxystrobin, pyrazophos, pyrizenca Lub, pyributicarb, pyrifenox, pyrimethanil, pyriophenone, pyroquilon , Quinoclamine, Quinoxyfen, Quintozene, Japanese Knotweed Extract (Reynoutria sacha linensis extract), sedaxane, silthiofam, simeconazole, sodium 2-fluoride Phenylphenoxide, sodium bicarbonate, sodium pentachlorophenoxide, spiro Xamine, sulfur, SYP-Z048, tar oil, tebuconazole, tebufloquine, tecna Zen, tetraconazole, thiabendazole, thifluzamide, thiophanate methyl, Ram, tiadinil, tolclofos-methyl, tolylfluanid, triadimefon, triazidimefon Menol, triazoxide, tricyclazole, tridemorph, trifloxystrobin , Triflumizole, Triforine, Triticonazole, Validamycin, Valifenale , Valifenal, Vinclozolin, Zineb, Ziram, Zoxamide, Candida oleioides Candida oleophila, Fusarium oxysporum, Gliocladium spp., Phlebiopsis gigantea s 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-dinitro Naphthalene, 1-chloro-2-nitropropane, 2-(2-heptadecyl-2-imidazo 2,3-dihydro-5-phenyl-1,4-dithiin, 1 ,1,4,4-tetraoxide, 2-methoxyethyl mercuric acetate, 2-methoxyethyl chloride Mercury, 2-Methoxyethylmercuric silicate, 3-(4-chlorophenyl)-5-methylrhodanine 4-(2-nitroprop-1-enyl)phenyl thiocyanate , Ampropylphos, Anilazine, Adithiram, Barium polysulfide, Bayer 3239 4. Benodani, Benquinox, Bentallon, Benzamacryl, Benzamacryl-I Sobutyl, Benzamorph, Binapacryl, Bis(methylmercury) sulfate, Bis(tributylsulfate) Cadmium Calcium Copper Zinc Chromate Sulfate (ca dmium calcium copper zinc chromate sulfate), carbamorph, CECA, clobenzyl Azone, chloraniformethane, chlorphenazole, chlorquinox, climbazole , Copper bis(3-phenylsalicylate), Copper zinc chromate, Kufuraneb, Copper hydrazine sulfate Um, cuprobam, ciclafuramide, cypendazole, ciproflam, decaphentin, Dicloron, Diclozolin, Diclobutrazol, Dimethirimol, Dinokton, Dinosul Hong, dinotervon, dipyrithione, ditalimfos, dodizin, drazoxolone, EBP , ESBP, etaconazole, etham, etilim, fenaminosulf, fenapanil, Fenitropan, fluotrimazole, flucarbanil, fluconazole, fluconazole -Cis, Flumecyclox, Furofanate, Glyodine, Griseoful Bin, Halakurinate, Hercules3944, Hexylthiophos, ICIA08 58, Isopamphos, Isovalerion, Mebenil, Mecarbinzide, Metazoxolone, Me Tofloxam, methylmercuric dicyandiamide, metsulfovax, milneb, muco Phosphoric anhydride, Mycozolin, N-3,5-dichlorophenylsuccinimide, N-3 -Nitrophenylitaconimide, Natamycin, N-Ethylmercurio-4-toluene Sulfonanilide, Nickel bis(dimethyldithiocarbamate), OCH, Phenyl water Silver dimethyldithiocarbamate, phenylmercuric nitrate, phosdifen, prothiocarb, Prothiocarb hydrochloride, pyracarbollide, pyridinitrile, pyroxalol, piroxifen quinacetol, quinacetol sulfate, quinazamide, quinconazole, rabenzazole, Salicylanilide, SSF-109, Sultropene, Tecolum, Thiazifluor, Thiothio Fen, thiochlorphenhim, thiophanate, thioquinox, thioximide, tri Amiphos, Triarimol, Triazbutyl, Trichlamide, Urvacid, Zarilamide, and any combination thereof.

[0493] Synergist compositions containing compounds of formula I and their uses are described in U.S. Pat. No. 9,526,245 (2 Issued on December 27, 2016), Issue No. 10045533 (issued on August 14, 2018), No. 9532570 (issued January 3, 2017), No. 10045534 (issued January 3, 2018) (issued on August 14, 2017), No. 9538753 (issued on January 10, 2017), and No. The full contents of each issue are listed in issue 10051862 (published on August 21, 2018). is incorporated herein by reference.

[0494] In some embodiments, the compositions of the present invention further comprise at least one plant health stimulant. In some embodiments, the fungicidal mixture of the present invention comprises at least one plant health stimulant. Further includes:

[0495] In some embodiments, the plant health stimulant is an organic compound, an inorganic fertilizer, or a micronutrient donor. -, biocontrol agents and inoculants.

[0496] Uses and applications of the compositions described herein: The present invention also relates to a method for controlling and / or preventing fungal pathogen infestation in a plant, comprising the steps of: Any one of the compositions or mixtures described herein may be applied to soil, plants, roots, leaves, seeds, fungi, spraying in areas where infestations are to be prevented, thereby preventing infestations of plants; Methods are also provided, including controlling and / or preventing fungal pathogen infestation.

[0497] The present invention also relates to a method for the control and / or prevention of fungal infestations in plants. Any one of the compositions or mixtures described herein is also provided.

[0498] The present invention also relates to the method for controlling and / or preventing fungal infestations in plants, comprising administering to said plants the method described herein. Use of any one of the compositions or mixtures is also provided.

[0499] The present invention also relates to a method for controlling and / or preventing fungal diseases of plants and / or soil. A method comprising administering any one of the compositions or mixtures described herein to soil, plants, roots, , leaves, seeds, fungal locations, and / or locations where infestation is to be prevented, and / or preventing fungal diseases of plants and / or soil by A method is also provided.

[0500] The present invention also relates to a method for the control and / or prevention of fungal diseases of plants and / or soil. There is also provided any one of the compositions or mixtures described herein for use.

[0501] The present invention also relates to a method for controlling and / or preventing fungal diseases of plants and / or soil. Also provided is the use of any one of the compositions or mixtures described herein.

[0502] In some embodiments, the composition or mixture is applied to a part of a plant, an area adjacent to a plant, a plant soil in contact with plants, soil adjacent to plants, any surfaces adjacent to plants, soil in contact with plants It may be applied to any surface, seed, and / or equipment used in agriculture.

[0503] In some embodiments, the composition or mixture comprises a concentration of from 5 g / ha to 150 g / ha of a compound of formula I. In some embodiments, the composition or mixture is a compound of formula I. In some embodiments, the composition or mixture is applied at a rate of 6.25 g / ha of The compound of formula I is applied at a rate of 10 g / ha. In some embodiments, the composition or mixture The plant is sprayed with a rate of 12.5 g / ha of the compound of formula I. In some embodiments, the composition Or the mixture is sprayed at a rate of 20 g / ha of the compound of formula I. In some embodiments, The composition or mixture is applied at a rate of 75 g / ha of the compound of formula I. In the present invention, the composition or mixture is applied in an amount of 100 g / ha of the compound of formula I. In an embodiment, the composition or mixture is applied at a rate of 125 g / ha of the compound of formula I. .

[0504] In some embodiments, the composition or mixture is applied at the time of sowing.

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

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

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

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

[0509] In some embodiments, the composition or mixture is applied more than once during the growing season.

[0510] In some embodiments, the compositions or mixtures are administered as foliar or seed treatments and / or soil applications. It is distributed as.

[0511] The present invention also provides a method for controlling and / or preventing fungal pathogen infestation in plants, comprising the steps of: A fungicidal effective amount of a compound of formula (I):

[0512] [ka] The compound having the formula (I) and at least one adjuvant are administered to the soil, plant, root, leaf, seed, or stem of the plant. Spray at the location of the fungus and / or where you want to prevent its infestation, thereby preventing it from reaching the plant. and controlling and / or preventing fungal pathogen infestation of the plant, wherein the adjuvant comprises (i) polyalkylene oxide alkyl ethers, (ii) siloxane polyalkylene oxide copolymers, (iii) esters of fatty acids, (iv) Vinylpyrrolidone and its derivatives, and (v) Sugar surfactants Also provided is a method, wherein the method is selected from the group consisting of:

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

[0514] [ka] The compound having the formula (I) and at least one adjuvant are administered to the soil, plant, root, leaf, seed, or stem of the plant. Spray at the location of the fungus and / or where you want to prevent its infestation, thereby killing the plants and and / or to control and / or prevent fungal diseases in soil, , (i) polyalkylene oxide alkyl ethers, (ii) siloxane polyalkylene oxide copolymers, (iii) esters of fatty acids, (iv) Vinylpyrrolidone and its derivatives, and (v) Sugar surfactants Also provided is a method, wherein the method is selected from the group consisting of:

[0515] The present invention provides a method for improving the biological activity of a compound of formula I against a fungal pathogen, comprising the steps of: The method comprises administering to the patient a compound of formula I:

[0516] [ka] and applying the compound of formula I to the skin, thereby improving the biological activity of the compound of formula I. Bunt, (i) polyalkylene oxide alkyl ethers, (ii) siloxane polyalkylene oxide copolymers, (iii) esters of fatty acids, (iv) Vinylpyrrolidone and its derivatives, and (v) Sugar surfactants The method is selected from the group consisting of:

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

[0518] The present invention also provides (a) the control and / or prevention of fungal pathogen infestation in plants, and / or (b) the prevention and / or treatment of plants with fungal pathogens. For the control and / or prevention of fungal diseases of plants and / or soil, Formula (I):

[0519] [ka] As well as compounds having the formula (i) polyalkylene oxide alkyl ethers, (ii) siloxane polyalkylene oxide copolymers, (iii) esters of fatty acids, (iv) Vinylpyrrolidone and its derivatives, and (v) Sugar surfactants The present invention also provides the use of at least one adjuvant selected from the group consisting of:

[0520] The present invention also provides (a) the control and / or prevention of fungal pathogen infestation in plants, and / or (b) the prevention and / or treatment of plants with fungal pathogens. For use in the control and / or prevention of fungal diseases of plants and / or soil , Formula (I):

[0521] [ka] As well as compounds having the formula (i) polyalkylene oxide alkyl ethers, (ii) siloxane polyalkylene oxide copolymers, (iii) esters of fatty acids, (iv) Vinylpyrrolidone and its derivatives, and (v) Sugar surfactants Also provided is at least one adjuvant selected from the group consisting of:

[0522] The present invention relates to a compound of formula (I):

[0523] [ka] To improve the biological activity of the compound of (i) polyalkylene oxide alkyl ethers, (ii) siloxane polyalkylene oxide copolymers, (iii) esters of fatty acids, (iv) Vinylpyrrolidone and its derivatives, and (v) Sugar surfactants The present invention provides the use of at least one adjuvant selected from the group consisting of:

[0524] The present invention relates to a compound of formula (I):

[0525] [ka] For use in improving the biological activity of a compound of (i) polyalkylene oxide alkyl ethers, (ii) siloxane polyalkylene oxide copolymers, (iii) esters of fatty acids, (iv) Vinylpyrrolidone and its derivatives, and (v) Sugar surfactants The present invention provides an adjuvant selected from the group consisting of:

[0526] Preferred adjuvants are described herein above.

[0527] In some embodiments, the compound of formula I and the adjuvant are administered simultaneously. In an embodiment, the compound of formula I and the adjuvant are applied 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 dispensed together. In some cases, the compound of formula I and the adjuvant are applied together as a tank mix. In an embodiment, the compound of formula I and the adjuvant are formulated as a single composition. In some embodiments, the adjuvant formulated with the compound of formula I in the composition is a virulent It is a combination adjuvant that can be tank mixed with the compound of formula I or, for example, can be administered separately. Adjuvants that are applied separately by spraying are add-on adjuvants. do.

[0529] In some embodiments, more than one adjuvant is applied, and at least one adjuvant One adjuvant is a built-in adjuvant, and at least one adjuvant is an add-on adjuvant. It's a bunt.

[0530] In some embodiments, the compound of formula I is applied at a rate ranging from 5 g / ha to 150 g / ha. In some embodiments, the compound of formula I is applied at a rate of 10 g / ha.

[0531] The compounds of formula I and compositions and mixtures containing the compounds of formula I are effective in treating a variety of fungal pathogens. It can be sprayed to control and / or prevent diseases of the body and its associated In some embodiments, the fungal pathogen is Leaf Blotch of Wheat ( Mycosphaerella graminicola, anamorph, wheat pathogen Zymoseptoria tritici), Wheat Brown Rust (Puccinia tritici) ticina), Stripe Rust (Puccinia striiformis f. s p. tritici), Scab of Apple (Venturia inaequal is), Blister Smut of Maize (corn smut fungus) (Ustilago maydis), Powdery Mildew of Grapevine Uncinula necator), Barley scald (Uncinula necator) Rhynchosporium secalis), Blast of Rice (Magna porche grisea), Rust of Soybean (Asian soybean rust fungus (Phak opsora pachyrhizi), Glume Blotch of Wheat (Glume Blotch of Wheat Leptosphaeria nodorum, Powdery Mildew of Wheat Powdery mildew fungus (Blumeria graminis f. sp. tritici), powdery mildew of barley Mildew of Barley (Blumeria graminis f. sp. hordei), Powdery Mildew of Cucurbits (Erysiphe cichoracearum), Anthracnose of Cucurbits (G lomerella lagenarium), Leaf Spot of Beet (Sugar Beet Brown Spot Fungus) (Cercospora beticola), Early Blight of Tomato Alternaria solani), and Net Blotch of Barley It is one of the pathogenic fungi (Pyrenophora teres).

[0532] In some embodiments, the fungal pathogen is Leaf Blotch of Wheat ( Mycosphaerella graminicola, anamorph, wheat pathogen Zymoseptoria tritici), Wheat Brown Rust (Puccinia tritici) ticina), Stripe Rust (Puccinia striiformis f. s p. tritici), Scab of Apple (Venturia inaequal is), Blister Smut of Maize (corn smut fungus) (Ustilago maydis), Powdery Mildew of Grapevine Uncinula necator), Barley scald (Uncinula necator) Rhynchosporium secalis), Blast of Rice (Magna porche grisea), Rust of Soybean (Asian soybean rust fungus (Phak opsora pachyrhizi), Glume Blotch of Wheat (Glume Blotch of Wheat Leptosphaeria nodorum, Powdery Mildew of Wheat Powdery mildew fungus (Blumeria graminis f. sp. tritici), powdery mildew of barley Mildew of Barley (Blumeria graminis f. sp. hordei), Powdery Mildew of Cucurbits (Erysiphe cichoracearum), Anthracnose of Cucurbits (G lomerella lagenarium), Leaf Spot of Beet (Sugar Beet Brown Spot Fungus) (Cercospora beticola), Early Blight of Tomato Alternaria solani), and Net Blotch of Barley It is one of the pathogenic fungi (Pyrenophora teres).

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

[0534] In some embodiments, the plant or soil disease is septoria, brown spot (septoria), leaf rust, yellow spot (yellow spot), Rust, Powdery Mildew, Barley Scald (Rhyncosporium), Net Spot (Pyrenophora), Comb Microduchium majus, Sclerotinia, Downy mildew , Phythopthora, Cercosporea beticola, Ramula ria) and Sigatoka disease (ASR. Sigatoka negra.).

[0535] The method of the present invention can be used to grow crops such as, but not limited to, sugarcane, rice, maize, etc. monocotyledons, such as sorghum, and / or beets (such as sugar beet or fodder beet) ) dicotyledonous crops; fruits (pomes, drupes, or soft fruits, e.g. apples, peaches, etc.); Citrus, plum, peach, almond, cherry, strawberry, raspberry, or blackberry legumes (beans, lentils, peas, or soybeans); oleaginous plants ( Rapeseed, mustard, poppy, olive, sunflower, palm, castor oil plant, cocoa bean, or rat cucumber plants (mallow, cucumber or melon); fiber plants (cotton, alfalfa, etc.) citrus fruits (oranges, lemons, grapefruit, or mandarin oranges); vegetables (spinach, lettuce, cabbage, carrots, tomatoes, etc.) Tomato, potato, cucurbit, or pepper; Lauraceae (avocado, cinnamon, etc.) or camphor, etc.); tobacco; nuts; coffee; tea; vines; hops; drench bananas; rubber plants; and ornamental plants (flowering, shrubs, broad-leaved, or evergreen trees, e.g. This refers to any crop, including arable land (e.g. conifers).

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

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

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

[0539] Compounds of formula I and compositions thereof are disclosed in U.S. Pat. No. 6,393,343, the entire contents of which are incorporated herein by reference. Plant pathogenic fungi described in Patent Publication No. 2018-0000082 (filed January 4, 2018) It may also be used as a seed treatment to prevent or control.

[0540] The subject invention also relates to a method for controlling or preventing fungal infestation in plants or protecting plants from fungal infestation. A method of protecting a plant comprising administering any one of the compositions or mixtures disclosed herein to the plant. Also provided is a method comprising applying to a seed adapted to produce the plant.

[0541] The subject invention also relates to a method for cultivating plant seeds or seedlings to produce plants resistant to fungal infestation. A method of treating a cancer, comprising implanting any one of the compositions or mixtures disclosed herein. Also provided is a method comprising applying to a seed or seedling of the plant.

[0542] The subject invention also provides a method for protecting plants from fungal infestation, comprising the steps of: Also provided is a method comprising applying any one of the compositions or mixtures to the growing environment.

[0543] The subject invention also relates to methods for cultivating plant seeds using any one of the compositions or mixtures disclosed herein. Also provided are plants that are resistant to fungal infestation by treating them with one or more of the following:

[0544] The subject invention also relates to the inoculation of plant seeds or seedlings with any of the compositions or mixtures disclosed herein. Plant species adapted to produce plants resistant to fungal infestations, treated with either The seedlings or seedlings are also provided.

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

[0546] The subject invention also relates to the use of any of the mixtures disclosed herein to produce a germicidal composition. The subject invention also provides the use of any one of the compositions disclosed herein. Also provided is the use of any one of the mixtures disclosed herein for the manufacture of

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

[0548] [ka] and a liquid carrier, comprising: a) Select a liquid carrier such that the solubility of the compound of formula I in the liquid carrier is less than 5000 ppm. , b) maintaining the pH value of the composition in the range of 5 to 7.5; c) maintaining the moisture content of the composition at less than 0.5% by weight, based on the total weight of the composition; d) (i) at least one stabilizing surfactant having crystal growth inhibiting properties, or ii) adding a stabilization system having crystal growth inhibiting properties to the liquid composition, and / or e) formulating the composition to have a viscosity of at least 500 cP; Also provided are methods of improving the stability of compositions comprising the compounds of formula I. do.

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

[0550] [ka] and a liquid carrier, the method comprising: selecting a liquid carrier, the solubility of the compound of formula I in the liquid carrier being 5000 ppm or less; The present invention also provides a method,

[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 relates to a compound of formula I:

[0553] [ka] and a liquid carrier, the method comprising: maintaining the pH value of the composition in the range of 5 to 7.5.

[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 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. H is approximately 7.5.

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

[0557] The present invention also relates to a compound of formula I:

[0558] [ka] of a pH adjuster for improving the stability of an aqueous concentrated suspension (SC) composition containing the compound Use is also provided.

[0559] The present invention also relates to a compound of formula I:

[0560] [ka] A pH value for improving the stability of an aqueous suspoemulsion (SE) composition containing the compound of The use of a modifier is also provided.

[0561] The present invention also relates to a compound of formula I:

[0562] [ka] A method for improving the stability of a liquid composition comprising a compound of formula (I) and a liquid carrier, comprising: and maintaining the moisture content at less than 0.5% by weight based on the total weight of the composition. .

[0563] The present invention also relates to a compound of formula I:

[0564] [ka] 2. A method for improving the stability of a liquid composition comprising a compound of formula (I) and a liquid carrier, comprising: (ii) at least one stabilizing surfactant having crystal growth inhibiting properties; Also provided is a method that includes adding a stabilizing system having the properties to a liquid composition.

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

[0566] In some embodiments, at least two stabilizing surfactants are added. In one embodiment, the at least two stabilizing surfactants are at least one polyalkyleneoxy A nonionic derivative of doped polyaryl ether and at least one polyalkyleneoxy group. Includes anionic derivatives of aryl polyethers.

[0567] The present invention also relates to a compound of formula I:

[0568] [ka] Polyalkylene oxide alkyl groups for controlling the solubility and / or degradation of compounds of The present invention also provides the use of at least one stabilizing surfactant having a diphenyl ether structure.

[0569] In some embodiments, an amide having the structure of a polyalkylene oxide polyaryl ether is The stabilized surfactant is a non-ionic derivative of polyalkylene oxide polyaryl ether. In some embodiments, the polyalkylene oxide polyaryl ether has the structure The stabilizing surfactants used are anionic derivatives of polyalkylene oxide polyaryl ethers. It is.

[0570] In some embodiments, the method further comprises selecting a liquid carrier, comprising: The solubility of compounds of type I is less than 5000 ppm.

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

[0572] In some embodiments, the method further comprises reducing the water content of the composition to 0.5 wt. %.

[0573] In some embodiments, the method further comprises: (i) at least one stable species having crystal growth inhibition properties; or (ii) a stabilizing system with crystal growth inhibiting properties to the liquid composition. It further includes:

[0574] The present invention also relates to a compound of formula I:

[0575] [ka] A method for improving the stability of a liquid composition comprising a compound of formula (I) and a liquid carrier, the method comprising: and formulating the composition to have a viscosity of at least 500 cP.

[0576] In some embodiments, the stable liquid composition is a concentrated 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 concentrate (EC) composition.

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

[0581] Methods for preparing compositions containing compounds of formula I The present invention provides a method for preparing the concentrated suspension (SC) composition disclosed herein, comprising the steps of: (1) Mixing an agriculturally acceptable inert additive with an aqueous liquid carrier to obtain a premix. Step (2) Adding a compound of formula I to the premix obtained in step (1) to obtain a mixture. Tep, and (3) milling the mixture obtained in step (2) to obtain the desired composition. The present invention provides a method comprising:

[0582] In some embodiments, the method further comprises adding additional additives to the mixture prior to grinding the mixture in step (2). The method includes adding to the mixture of

[0583] The present invention relates to a method for preparing the suspoemulsion (SE) compositions disclosed herein. There was, (1) Mixing an agriculturally acceptable inert additive with an aqueous liquid carrier to obtain a premix. Step (2) The compound of formula I and at least one adjuvant are mixed with the protease obtained in step (1). adding to the remix to obtain a mixture; and (3) milling the mixture obtained in step (2) to obtain the desired composition. The present invention provides a method comprising:

[0584] In some embodiments, step (1) comprises 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 provides a method for preparing the oil dispersion (OD) composition disclosed herein, comprising the steps of: (1) Mix an agriculturally acceptable inert additive with a non-aqueous liquid carrier to form a premix. obtaining a step of (2) Adding a compound of formula I to the premix obtained in step (1) to obtain a mixture. Tep, and (3) milling the mixture obtained in step (2) to obtain the desired composition. The present invention provides a method comprising:

[0586] The present invention provides a method for preparing the emulsion concentrate (EC) composition disclosed herein, comprising the steps of: (1) Mix an agriculturally acceptable inert additive with a non-aqueous liquid carrier to form a premix. obtaining a step of (2) Adding a compound of formula I to the premix obtained in step (1) to obtain a mixture. Tep, and (3) filtering the solution of step (2) to obtain the desired composition. The present invention provides a method comprising:

[0587] Each embodiment disclosed in this specification is applicable to each other disclosed embodiment. Thus, all combinations of the various elements described herein are contemplated as being within the scope of the present invention. In addition, if an enumeration is presented, the enumeration may be any one of the elements of the enumeration. shall be considered as a bare disclosure.

[0588] This invention will be better understood by reference to the Experimental Details set forth below. Those skilled in the art will appreciate that certain details are more fully described in the claims which follow. It will be readily understood that the described experiments are only illustrative of the present invention. The present invention is illustrated by, but not limited to, the following examples.

[0589] Experimental Section The compounds of formula I are disclosed in WO 2015 / 103144 and WO 2015 / 103145. The compositions can be prepared as described in US Pat. No. 5,314,522.

[0590] It is difficult to prepare stable compositions containing the compound of formula I due to the high sensitivity of the compound. Numerous attempts have been made to stabilize the composition. Some of the results are described below. do.

[0591] The compounds of formula I are added to azidopropyl ether 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), vinylpyrrolidone and acetic acid. Block copolymer with vinyl (VP / VA), siloxane polyalkylene oxide copolymer Rimer (Silwet® L-077), ethoxylated tridecyl alcohol 1 3 / 9 (Trycol®), alkoxylated alcohols (Agnique®), (BP420), and fatty acid methyl esters (Agnique® ME 18 RDF).

[0593] Example 1: 450 SC composition without adjuvant Concentrated Suspension (SC) containing 450 g / L of the compound of formula I without adjuvant The formulations were prepared as follows.

[0594] Step I: Preparation of an agriculturally acceptable inert additive premix Add soft water and Van Gel® B to the container and mix (high shear) to form a solution. The contents of the vessel were heated to 60° C. 54 (TSP 54) was heated to 50-60°C and slowly added to the vessel. ragil® WP, Soprophor® 3D33, KH 2 PO 4 , Na 2 HPO 4 and SAG 1572 were added to the homogenous solution.

[0595] Step II: Preparation of Compounds of Formula I A compound of formula I (40% w / w) is added to the premix containing the surfactant, 90 Bead mill (0.8-1.2 mm beads) until a particle size distribution of <5 μm is reached The suspension was milled at 0.5° C. The milled suspension was discharged from the reactor into a new vessel. did.

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

[0597] The compositions are summarized in Table 1.

[0598] [Table 1-1]

[0599] [Table 1-2]

[0600] Stability results: The physical and chemical stability of the composition of Example 1 was evaluated under various conditions, including CIPAC conditions. The stability results 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 was measured and was greater than 95%.

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

[0604] Step I: Preparation of an agriculturally acceptable inert additive premix Add soft water and Van Gel® B to the container and mix (high shear) to form a solution. The contents of the vessel were heated to 60° C. Supragi 54 (TSP 54) was heated to 50-60°C and slowly added to the vessel. l®WP, Soprophor®3D33, KH 2 PO 4 , Na 2 HPO 4 and SAG 1572 were added to the homogenous solution.

[0605] Step II: Preparation of Compounds of Formula I A compound of formula I (40% w / w) was added to the premix containing the surfactant. Bead mill (0.8-1.2 mm beads) until a particle size of d90<5 μm is reached. The suspension was milled in a 200° C. The milled suspension was discharged from the reactor into a new vessel. Ta.

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

[0607] The compositions are summarized in Table 3.

[0608] [Table 3-1]

[0609] [Table 3-2]

[0610] Stability results: The composition of Example 2 was stored at 54° C. for 2 weeks. No crystal growth was observed. The concentration of the compound was measured and was slightly less than 95%.

[0611] Example 3: Vinylpyrrolidone / vinyl acetate copolymer and Silwet® L-0 450SC and 660SC compositions, including mixtures with 77 One was a mixture of 450 g / L of the compound of formula I and two built-in adjuvants (VP / VA and and Silwet® L-077), the other containing 660 g / L of the compound of formula I. and two built-in adjuvants (VP / VA and Silwet® L-0 77) was prepared as follows:

[0612] Step I: Preparation of an agriculturally acceptable inert additive premix Add soft water (and Van Gel® B for the 450 SC composition) to the container. The contents of the vessel were heated to 60° C. and mixed (high shear) to form a solution. Heat PROPHOR® TS / 54 (TSP 54) to 50-60°C and dissolve in water. Supragil® WP, Soprophor® )3D33, KH 2 PO 4 , Na 2 HPO 4 and SAG 1572 were added to the homogeneous solution. Ta.

[0613] Step II: Preparation of Compounds of Formula I A compound of formula I (40% w / w) was added to the premix containing the surfactant. Bead mill (0.8-1.2 mm beads) until a particle size of d90<5 μm is reached. The suspension was milled in a 200° C. The milled suspension was discharged from the reactor into a new vessel. Ta.

[0614] Step III: Completion of the composition Propylene glycol and Silwet® L-077 were mixed until a uniform suspension was formed. Add the milled suspension until a viscosity of 1600-2200 cP is achieved. Soft water and a 2% AgRH23 solution were added to the suspension while mixing at 100°C. The viscosity was measured using a viscometer according to CIPAC method MT 192. Therefore, measurements were taken.

[0615] The 450 SC compositions are summarized in Table 4, and the 660 SC compositions are summarized in Table 5.

[0616] [Table 4-1]

[0617] [Table 4-2]

[0618] Stability results: The compositions in Table 4 were stored at 54° C. for 2 weeks. No crystal growth was observed. The concentration of the substance was measured and was found to be slightly less than 95%.

[0619] [Table 5-1]

[0620] [Table 5-2]

[0621] Stability results: The stability results for the compositions in Table 5 are summarized in Table 6 below.

[0622] [Table 6]

[0623] Example 4: 450 SC Composition with Two Built-in Adjuvants 450 g / L of the compound of formula I and two built-in adjuvants (PVP and Sil Wet (registered trademark L-077) was added to a concentrated suspension (SC) formulation as follows: Prepared.

[0624] Step I: Preparation of an agriculturally acceptable inert additive premix Add soft water and Van Gel® B to the container and mix (high shear) the solution. The contents of the vessel were heated to 60°C. SOPROPHOR® TS / 54 ( TSP 54) was heated to 50-60°C and slowly added to the vessel. l®WP, Soprophor®3D33, KH 2 PO 4 , Na 2 HPO 4and SAG were added.

[0625] Step II: Preparation of Compounds of Formula I A compound of formula I (40% w / w) is added to the premix containing the surfactant therein; A suspension was formed. The suspension was milled in a bead mill (0.8–1 The suspension was milled in a 1.2 mm bead mill. The suspension was transferred from the reactor to a new vessel. Discharged.

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

[0627] The compositions are summarized in Table 7 below.

[0628] [Table 7-1]

[0629] [Table 7-2]

[0630] Example 5: VP / VA, Agnique® BP 420 and Agnique 300 SE Composition with ME 18 RD-F 300 g / L of the compound of formula I and three built-in adjuvants (VP / VA, Agn Agnique® BP 420 and Agnique® ME 18 RD -F) was prepared as follows:

[0631] Step I: Preparation of an agriculturally acceptable inert additive premix The soft water and Van Gel® B were added to the vessel and mixed (high shear). The contents of the vessel were heated to 60° C. SOPROPHOR® TS / 54 (TSP 54) was heated to 50-60°C and slowly added to the vessel. Supragil® WP, Soprophor® 3D33, KH 2 PO 4 , Na 2 HPO 4 and SAG was added to the solution.

[0632] Step II: Preparation of Compounds of Formula I A compound of formula I (40% w / w) is added to the premix containing the surfactant therein; A suspension was formed. The suspension was milled in a bead mill (0.8–1 The suspension was milled in a 1.2 mm bead mill. The milled suspension was removed from the reactor and Discharged into a new container.

[0633] Step III: Preparation of the organic phase Agnique® ME RDF, Atlox™ 4914, Atlas (trademark) G5002L, Genapol® X80 and Agnique® Add BP 420 to the container and mix until a homogeneous solution is obtained. Before addition, the contents of the vessel were mixed at least once until a droplet size of D90 = 10 μm was reached. Mixed (high shear) for 0 minutes.

[0634] Step IV: Completion of the composition Propylene glycol and VP / VA were added to the milled suspension until a uniform suspension was obtained. The SE solution was gradually added to the milled suspension in three doses. Between each dose, add A while mixing until a viscosity of 1600-2200 cP is reached. Add tlox™ 4913, soft water and Ag RH 23 2% solution. The viscosity was measured using a viscometer according to CIPAC method MT 192. was measured.

[0635] The compositions are summarized in Table 8 below.

[0636] [Table 8-1]

[0637] [Table 8-2]

[0638] [Table 8-3]

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

[0640] Step I: Preparation of an agriculturally acceptable inert additive premix The soft water and Van Gel® B were added to the vessel and mixed (high shear). The contents of the vessel were heated to 60° C. SOPROPHOR® TS / 54 (TSP 54) was heated to 50-60°C and slowly added to the vessel. Supragil® WP, Soprophor® 3D33, KH 2 PO 4 , Na 2 HPO 4 and SAG was added to the solution.

[0641] Step II: Preparation of Compounds of Formula I A compound of formula I (40% w / w) is added to the premix containing the surfactant therein; A suspension was formed. The suspension was milled in a bead mill (0.8–1 The suspension was milled in a 1.2 mm bead mill. The milled suspension was removed from the reactor and Discharged into a new container.

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

[0643] Step IV: Completion of the composition Propylene glycol and PVP were added to the milled suspension to obtain a uniform suspension. The SE solution was slowly added to the milled suspension in three doses. Between each dose, add Atl while mixing until a viscosity of 1600-2200 cP is reached. ox4913, soft water and Ag RH 23 2% solution were added. Mix until homogeneous. The mixture was allowed to stand until a solution was obtained. The viscosity was measured by a viscometer according to CIPAC method MT 192. I measured it.

[0644] The compositions are summarized in Table 9 below.

[0645] [Table 9-1]

[0646] [Table 9-2]

[0647] Example 7: Concentrated Suspension (SC) Formulations without Stabilizing Surfactants at a pH of Approximately 7 Composition A concentrated suspension (S) containing 450 g / L of the compound of formula I and no stabilizing surfactant was prepared. C) The formulations were prepared as follows:

[0648] 4% Atlox(TM) 4913, 2% Ethylan(TM) NS 50 in water 0 LQ / Antarox® B 848, 0.5% Supragil Add 0.1% antifoam (SAG 1572) and a homogeneous solution. The mixture was mixed until smooth.

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

[0650] The remaining ingredients were placed into suspension, mixed, divided into vials, and placed in the room and oven.

[0651] The formulations are summarized in Table 10.

[0652] [Table 10]

[0653] Stability Results The SC composition was placed at room temperature and in an oven (54°C) for 24 hours and the concentration was examined. The decomposition of the compound of formula I was measured by observing the formation of solid particles. showed a significant decrease.

[0654] Example 8: Concentrated Suspension Composition with Stabilizing Surfactant at pH 3.5 The compound of formula I was added at 450 g / L and two stabilizing surfactants (Soprophor® A concentrated suspension containing 3D33 (trademark) and Soprophor® TS / 54 (trademark). A suspension liquid (SC) formulation was prepared as follows.

[0655] Step I: Preparation of an agriculturally acceptable inert additive premix Contains preheated SOPROPHOR® TS / 54 (TSP 54) The soft water was slowly added to the container. The contents of the container were mixed until a homogeneous solution was obtained. Heat to 65° C. Supragil® WP, Soprophor® mark) 3D33, KH 2 PO 4 , Na 2 HPO 4 and SAG™ 1572 in solution. Added.

[0656] Step II: Preparation of Compounds of Formula I A compound of formula I (40% w / w) is added to the premix containing the surfactant therein; A suspension was formed. The suspension was milled in a bead mill (0.8–1 The suspension was milled in a 1.2 mm bead mill. The milled suspension was removed from the reactor and Discharged into a new container.

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

[0658] The compositions are summarized in Table 11.

[0659] [Table 11-1]

[0660] [Table 11-2]

[0661] Stability results: After 2 weeks in a 54°C oven, the concentration decreased by 6% in accelerated storage. Particles were observed, however the concentration of the compound of formula I was reduced.

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

[0663] Example 9: Concentrated Suspension Compositions with Stabilizing Surfactants at pH 4 and 8 Table 12 shows the results of two stabilizing surfactants (Soprophor® 3D 33 and Soprophor® TS / 54) (BN 161213-5-Sop3d_TSP54_PG and BN 161213- 6-Sop3d_TSP54_PG). BN 161213-5-Sop3d_T SP54_PG has a low pH of 4 and BN 161213-6-Sop3d_T SP54_PG has a high pH of 8.

[0664] Neither composition was stable. The first composition had a low concentration in the oven. The viscosity of the second composition was measured by the CIPAC M method. The viscosity was measured by a viscometer according to T 192.

[0665] [Table 12]

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

[0667] In conclusion, to have a stable SC formulation, the pH of the composition should be in the range of 5.0 to 7.5. It is necessary to maintain

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

[0669] Step I: Premixing of inert additives in an agriculturally acceptable, non-aqueous carrier (fatty acid ester). Preparation of the Using a large round hole Silverson mixer, B was mixed under high shear (3000 rpm). entone SD-1 with Agnique ME 18 RD- F and mixed for 5 minutes.

[0670] 10 seconds -1 The mixture was milled in a colloid mill until the viscosity at 0.5° C. no longer increased significantly. The mixture was milled (50 times) in an IKA MagicLab. Viscosity was measured by the CIPAC method. Measured by viscometer according to MT 192.

[0671] Add Agnique® ME 18 RD-F to a suitable container and add pregel. Well, mixed for 5 minutes.

[0672] The emulsifier and dispersant were added and mixed for 15 minutes until uniform.

[0673] Step II: Preparation of Compounds of Formula I The compound of formula I was added under stirring and mixed until uniform. and mixed for 15 minutes.

[0674] Step III: Completion of the composition Eiger Mini Motor Mill (80% 0.75mm~1.0mm Beads Filling, 4000 The samples were milled at 1000 rpm for 15 minutes.

[0675] The formulations are summarized in Table 13.

[0676] [Table 13]

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

[0678] Step I: Premixing of inert additives in an agriculturally acceptable, non-aqueous carrier (fatty acid ester). Preparation of the Using a large round hole Silverson mixer, B was mixed under high shear (3000 rpm). entone SD-1 with Agnique ME 18 RD- F and mixed for 5 minutes.

[0679] 10 seconds -1 The mixture was milled in a colloid mill until the viscosity at 0.5° C. no longer increased significantly. The mixture was milled (50 times) in an IKA MagicLab. Viscosity was measured by the CIPAC method. Measured by viscometer according to MT 192.

[0680] Add Agnique® ME 18 RD-F to a suitable container and add pregel. Well, mixed for 5 minutes.

[0681] The emulsifier and dispersant were added and mixed for 15 minutes until uniform.

[0682] Step II: Preparation of Compounds of Formula I The compound of formula I was added under stirring and mixed until uniform. and mixed for 15 minutes.

[0683] Step III: Completion of the composition Eiger Mini Motor Mill (80% 0.75mm~1.0mm Beads Filling, 4000 The samples were milled at 1000 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 the mixture was homogeneous after mixing). After storage at 54°C for 2 weeks, chemical decomposition was observed (10% of compound of formula I). Less than % decomposed).

[0687] Example 12: 250 OD formulation 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 as in Example 10 and 11 was prepared using a similar process.

[0688] The formulations are summarized in Table 15.

[0689] [Table 15]

[0690] The composition of Example 12 was stored at 54° C. for two weeks, and no significant degradation of the compound of Formula I was observed. I couldn't.

[0691] Example 13: 250 OD Composition with Agnique® ME 18 RD-F (OD composition D): Step I: Premixing of inert additives in an agriculturally acceptable, non-aqueous carrier (fatty acid ester). Preparation of the Add Agnique® ME 18 RD-F to a suitable container and add pregel. Well, mixed for 5 minutes.

[0692] The emulsifier and dispersant were added and mixed for 15 minutes until uniform.

[0693] Step II: Preparation of Compounds of Formula I The compound of formula I was added under stirring and mixed until uniform. and mixed for 15 minutes.

[0694] 10 seconds -1 The mixture was milled in a colloid mill until the viscosity at 0.5° C. no longer increased significantly. The mixture was milled (50 times) in an IKA MagicLab. Viscosity was measured by the CIPAC method. Measured by viscometer according to MT 192.

[0695] Step III: Completion of the composition Eiger Mini Motor Mill (80% 0.75mm~1.0mm Beads Filling, 4000 The samples were milled at 1000 rpm for 15 minutes.

[0696] [Table 16]

[0697] [Table 17]

[0698] Example 14: EC Compositions Containing Compounds of Formula I Three emulsifiable concentrate (EC) compositions (A, B and C) each containing 50 g / L of the compound of formula I were and C) were prepared.

[0699] The process for preparing composition C is summarized below. (Compositions A and B can be prepared by similar processes.) It can be prepared using 1. Place Alkamuls® 14 / R (CO60) in a 50°C water bath / oven. The mixture was then thawed in a kettle. 2. Benzyl acetate and propylene carbonate were charged to the vessel and heated to 50°C. 3. The compound of formula I was added to the reactor with mixing until a clear solution was obtained. 4. Ninate® 60, TSP16 and Fused Alkamuls® Slowly add 14 / R (4) to the reactor while mixing until a clear solution is obtained. Ta. 5. Mixing was continued for 1 hour while the reactor was cooled to room temperature. 6. The solution was drained 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 C and C are summarized in Tables 21 and 22.

[0701] [Table 18]

[0702] Crystal formation was observed in this formulation after one 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 containing a compound of formula I and an adjuvant Example 15(a): SC Composition Tank-Mixed with Adjuvant Formulated in different concentrations as a built-in composition and / or as a tank-mix application. A composition comprising a compound of formula I and an adjuvant was used to inhibit the growth of wheat crops (BBCH 12 growth stage) Winter wheat plants (cultivar Alixan (Limagrain)) were treated on the .

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

[0710] The SC composition of Example 1 was formulated with Trycol® (0.2 or less per hectare). These are mixed with 0.4L per hectare or Silwet (0.01L per hectare). was added as a tank mix in a 200 L volume of water.

[0711] The compositions and mixtures were sprayed by hand-held sprayers 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 allowed to dry at room temperature for 1 h and then transferred to a climate chamber (24°C day / night). Incubated at 18°C, 16-hour light / 8-hour dark photoperiod, and 65% relative humidity. did.

[0713] Cut off the first leaf fragment and transfer it to a Petri dish containing adapted plain agar (1 Petri dish The segments contained Z. tritici strain Mg Tri-R6. Inoculate with a calibrated pycnospore suspension.

[0714] After inoculation, the petri dishes were placed in a climate chamber (temperature 20°C during the day / 17°C at night, 16 hours light / 8 hours dark). The plants are cultured under a 20-h light-dark photoperiod (day length, controlled relative humidity).

[0715] After 21 days of incubation, the intensity of infection, i.e., the number of Z. tritici strains infected with The surface area of ​​the leaf that is Rony formed is evaluated (quantitative criteria) and then expressed as a percentage of the untreated control. The bactericidal effect of each composition was determined. All data were analyzed using statistical software (XL The expected output from this step is is a measure of the biological bactericidal effect of a compound of formula I in the presence of

[0716] Disease assessment was performed 21 days postinoculation (dpi) by measuring the length of necrotic leaf segments. The intensity of infection was then determined as a percentage of the total length of the leaf sections.

[0717] Based on the area under the disease progression curve (AUDPC), a quantitative measure of disease severity over time, The efficacy of the 100% 15 ... Multiplying the average disease intensity between each pair of adjacent time points by the corresponding time interval A trapezoidal algorithm using the following formula was performed for each time interval.

[0718] Bactericidal efficacy was determined from AUDPC values ​​and expressed as a percentage of the untreated control.

[0719] Results and Discussion All Asian strains were tested against the wheat pathogen Zymoseptoria tritici strain Mg Tri-R6. All adjuvants tested alone had no effect on the control conditions. No significant fungicidal activity was observed against the wheat pathogen Z. tritici strain Mg Tri-R6. He had no gender.

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

[0721] The results showed that the addition of adjuvants reduced the wheat pathogen Zymoseptoria tritici 4 shows that the efficacy of the compound of formula I against the strain Mg Tri-R6 is increased.

[0722] As shown in Figures 1 and 2, one adjuvant, Trycol® or S By adding ilwet® (even in small amounts), Compared to spraying, the efficacy and effective fungicidal activity of the compound of formula I was increased.

[0723] The results show that the compound of formula I, SC, is ) in the tank mix significantly improved the bactericidal activity of the composition. did.

[0724] Without wishing to be bound by any theory, Silwet® L -077 and Trycol (the concentration of this adjuvant is based on the total weight of the composition, 3% by weight) reduces the surface tension of the leaf surface, thereby enhancing the bactericidal activity of the composition. The hypothesis is that this has improved efficacy.

[0725] As shown in Figures 4, 5 and 6, two adjuvants, Silwet® and Add Agnique® BP 420 and PVP or VP / VA. The efficacy and killing efficiency of the compound of formula I compared to spraying without adjuvant was The bacterial activity increased.

[0726] Agnique® BP 420 (Alcohol Ethoxylate Propoxylate) PVP or VP combinations with C16 and C18 or Silwet® The efficacy of the compound of formula I in the presence of / VA was compared with that of the compound of formula I without adjuvant. Increased compared to fabric.

[0727] Without wishing to be bound by any theory, S in combination with VP / VA ilwet® L-077 (siloxane polyalkylene oxide copolymer) The concentration of this adjuvant is up to 2% by weight, based on the total weight of the composition. The compound of formula I is then applied to the leaf by reducing tension, thereby spreading the composition over the leaf surface. It is hypothesized that this would increase the efficacy and effective fungicidal activity of the fungicide. The deposits of the composition on the surface are more spread out on the leaves, remain for a longer period and therefore are more resistant. Has rain characteristics.

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

[0729] All fungicides were applied in a volume equivalent to 200 L / ha in water or S solution (S solution is a mixture of The composition is diluted with water 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 OD compositions containing the compounds of formula I, OD composition with an equivalent volume of water or S solution (S solution refers to a solution in which the composition is diluted) (from Example 10, Table 13) was prepared and used 3 hours after preparation.

[0733] The first leaves of wheat plantlets, cultivar Alixan, were either untreated or treated with a compound of formula I. The OD formulation prototype A (from Example 10, Table 13) was used to detect wheat pathogens (Zymose ptoria tritici) strain Mg Tri-R6 (moderately resistant to DMI fungicides under controlled conditions) 21 days after inoculation with powder spores of the fungus, which is highly resistant to Qol fungicides, 10 g ai / ha and 20 g ai / ha. Disease was assessed using the intensity of infection. .

[0734] The results are shown in Figure 9.

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

[0736] Disease was assessed using the percentage of infection and the results are shown in Figure 10.

Claims

1. (a) a fungicidally effective amount of a compound of formula I: 【Chemistry 1】 and (b) Liquid carrier 1. A stable liquid composition comprising:

2. a) the solubility of the compound of formula I in the liquid carrier is less than 5000 ppm; b) the composition comprises at least one stabilizing surfactant; c) the pH of the composition is in the range of 5 to 7.5; d) the composition has a moisture content of less than 0.5% by weight based on the total weight of the composition; and and / or e) the composition has a viscosity of at least 500 cP; 2. The stable liquid composition of claim 1.

3. a) the composition comprises a nonionic stabilizing surfactant and an anionic stabilizing surfactant; fruit, b) the stabilizing surfactant is a tristyrylphenol ethoxylate phosphate ester 2,4,6-tri-(1-phenylethyl)-phenol polyglycoside having 54EO ether, ethoxylated tristyrylphenol, or a combination thereof; c) the composition comprises two stabilizing surfactants, the stabilizing surfactants being tris Styrylphenol ethoxylate phosphate esters and ethoxylated tristyrylphenols and / or d) the composition comprises a pH adjuster; 3. The stable liquid composition according to claim 1 or 2.

4. The non-ionic stabilizing surfactant is a polyalkylene oxide polyaryl ether. The anionic surfactant is a polyalkyleneoxy derivative. The anionic derivative of a cycloaliphatic polyaryl ether according to any one of claims 1 to 3. A stable liquid composition.

5. a) the liquid carrier is an aqueous liquid carrier and the composition is also a concentrated suspension (SC) composition; or a suspoemulsion (SE) composition, b) the liquid carrier is a non-aqueous liquid carrier, and the composition is also an oil dispersion (OD) composition. or an emulsion (EC) composition, The stable liquid composition according to any one of claims 1 to 4.

6. a) said compound of formula I is in the form of solid particles, said solid particles of said compound of formula I , suspended in said liquid carrier; or b) the compound of formula I is dissolved in the liquid carrier; A stable liquid composition according to any one of claims 1 to 5.

7. a) the concentration of the compound of formula I in said composition is 25 parts by weight based on the total weight of said stable composition; and / or b) the concentration of the compound of formula I in the stable liquid composition is from 300 g / L to 750 g / L L. A stable liquid composition according to any one of claims 1 to 6.

8. a) the composition is a solid diluent, a liquid diluent, a wetting agent, an adhesive, a thickener, a defoamer, a preservative additives, antioxidants, binders, fertilizers, antifreezes, additional pesticides, safeners, or any of the above. and / or b) The composition comprises phosphoric acid, urea, propyl gallate, dimethyl sulfoxide (DMS O), does not contain morpholine and / or N-methylpyrrolidone; A stable liquid composition according to any one of claims 1 to 7.

9. Any of claims 1 to 8, wherein the composition further comprises at least one adjuvant. A stable liquid composition according to claim 1.

10. The adjuvant is (i) polyalkylene oxide alkyl ethers, (ii) siloxane polyalkylene oxide copolymers; (iii) esters of fatty acids, (iv) vinylpyrrolidone and its derivatives, and (v) Sugar surfactant 10. The stable liquid composition of claim 9, selected from the group consisting of:

11. (a) a fungicidally effective amount of a compound of formula I: 【Chemistry 2】 and (b) (i) polyalkylene oxide alkyl ethers, (ii) siloxane polyalkylene oxide copolymers; (iii) esters of fatty acids, (iv) vinylpyrrolidone and its derivatives, and (v) Sugar surfactant At least one adjuvant selected from the group consisting of A bactericidal mixture comprising:

12. 12. The fungicidal mixture of claim 11, wherein the fungicidal mixture is a composition or a tank mix. thing.

13. a) the amount of the compound of formula I in the mixture is 1 to 99 parts by weight based on the total weight of the mixture; % by volume, b) the amount of the adjuvant in the mixture is between 0.1 and 9 based on the total weight of the mixture; Between 9% by weight c) the amounts of the compound of formula I and the adjuvant in the bactericidal mixture are adjusted according to the amount of the compound of formula I and the amount of the adjuvant in the bactericidal mixture; about 0.1 to 99% by weight based on the total weight of the article; and / or d) the weight ratio of said compound of formula I to said adjuvant is 50:1 to 1:50; A fungicidal mixture according to claim 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 propoxylate ester It is a tel. e) the adjuvant is an ethoxylated tridecyl alcohol or a polyoxyethylene lene(9) isotridecanol, f) The adjuvant is a blend of fatty acid esters and fatty alcohol alkoxylates. and / or g) the adjuvant is a mixture of methylated seed oil and polyglycerol esters 、 A fungicidal mixture according to any one of claims 11 to 13.

15. The vinylpyrrolidone derivative is a vinylpyrrolidone / vinyl acetate (VP / VA) copolymer.

15. The biocidal mixture of claim 14 which is a block copolymer.

16. a) the amount of VP / VA in the mixture is about 0.5 to 3 weight percent 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 The concentration is about 0.5 to 2.5% by weight based on the total weight of the composition; 16. The fungicidal mixture of claim 15.

17. (i) fungal pathogen infestation of plants or (ii) fungal disease of plants and / or soil A method for control and / or prevention, comprising the steps of: The method comprises administering a composition or mixture according to any one of claims 1 to 16 to soil, plants, Apply to the plant, roots, leaves, seeds, fungal sites and / or areas where you wish to prevent infestation. thereby preventing fungal pathogen infestation of plants or fungal diseases of plants and / or soil. The method includes removing and / or preventing the

18. (i) fungal pathogen infestation of plants or (ii) fungal disease of plants and / or soil A method of control and / or prevention, comprising the steps of: The method comprises administering to a patient a fungicidally effective amount of formula (I): 【Chemistry 3】 The compound having the formula (I) and at least one adjuvant are administered to the soil, plant, root, leaf, seed, or stem of the plant. Spray at the location of the fungus and / or where you want to prevent its infestation, thereby damaging the plant. and / or prevent fungal pathogen infestation or plant and / or fungal disease. and The adjuvant is (i) polyalkylene oxide alkyl ethers, (ii) siloxane polyalkylene oxide copolymers; (iii) esters of fatty acids, (iv) vinylpyrrolidone and its derivatives, and (v) Sugar surfactant The method of claim 1, wherein the

19. 1. A method for improving the biological activity of a compound of formula I against a fungal pathogen, comprising: The method comprises administering to the patient a compound of formula I: 【Chemistry 4】 thereby improving the biological activity of the compound of formula I, The adjuvant is (i) polyalkylene oxide alkyl ethers, (ii) siloxane polyalkylene oxide copolymers; (iii) esters of fatty acids, (iv) vinylpyrrolidone and its derivatives, and (v) Sugar surfactant The method of claim 1, wherein the

20. a) At least two adjuvants are sprayed, or at least two adjuvants are sprayed A compound of formula I is sprayed in the presence of b) The adjuvant is a block copolymer of vinylpyrrolidone and vinyl acetate (VP / VA). is a polymer, c) the adjuvant is a siloxane polyalkylene oxide copolymer; d) the adjuvant is polyvinylpyrrolidone; e) the adjuvant is a C16-C18 alcohol ethoxylated propoxylate ester It is a tel. f) the adjuvant is an ethoxylated tridecyl alcohol or polyoxyethylene (9) isotridecanol, g) the adjuvant is a blend of fatty acid esters and fatty alcohol alkoxylates and / or h) the adjuvant is a mixture of methylated seed oil and polyglycerol esters 、 20. The method of claim 18 or 19.

21. a) applying the compound of formula I in an amount ranging from 5 g / ha to 150 g / ha; b) spraying said compound of formula I and said adjuvant simultaneously or sequentially; c) tank mixing said compound of formula I and said adjuvant; d) formulating said compound of formula I and said adjuvant as a single composition, and / or Or e) spraying two or more adjuvants, wherein at least one of the adjuvants One is tank mixed with the compound of formula I and at least one of the adjuvants. Another is formulated with the compound of formula I. The method according to any one of claims 18 to 20.

22. a) The fungal pathogen is a fungal pathogen causing wheat leaf spot (Mycosphaerella graminico la), Anamorph: Wheat pathogen (Zymoseptoria tritici), Wheat brown rust (Wheat Brown Rust (Puccinia triticina), Stripe Rust (Wheat rust (Puccinia striiformis f. sp. tritici)), Apple scab (Scab of Apple) (Venturia inaequalis), Corn blister (B lister Smut of Maize (Ustilago maydis), Grape smut Powdery Mildew of Grapevine (Uncinula necator), Barley scald (Rhynchosporium secalis), rice Blast of Rice (Magnaporthe grisea), Soybean Rust (Rice Asian soybean rust (Phakopsora pachyrhizi), wheat rust Glume Blotch of Wheat (Leptosphaeria nodorum), wheat Powdery Mildew of Wheat (Blumeria graminis f. sp. tritici), Powdery Mildew of Barley (Barley powdery mildew) Powdery mildew (Blumeria graminis f. sp. hordei), powdery mildew (Powder Mildew Powdery mildew of cucurbits (Erysiphe cichoracearum), anthracnose of cucurbits (Anthracnose of Cucurbits) (Glomerella lagenarium), beets Leaf Spot of Beet (Cercospora beticola), Tomato Early Blight of Tomato (Alternaria solani), and and Net Blotch of Barley (Pyrenophora teres) cysts or b) The plant or soil fungal disease is brown spot (Septoria), red rust, yellow rust, Powdery mildew, barley rhyncosporium, pyrenophora, wheat red mold Microduchium majus, Sclerotinia, Downy mildew, Phytophthora blight (Phythopthora), sugar beet brown spot (Cercosporea beticola), leaf spot (Ramularia), Sigatoka disease (ASR. Sigatoka negra.) is one of the causes of Sigatoka disease. The method according to any one of claims 18 to 21.

23. Formula I: 【Chemistry 5】 and a liquid carrier, comprising: The method comprises: a) a liquid carrier, the solubility of the compound of formula I in the liquid carrier being less than 5000 ppm; choose, b) maintaining the pH value of the composition in the range of 5 to 7.5; c) maintaining the moisture content of the composition at less than 0.5% by weight, based on the total weight of the composition; d) (i) at least one stabilizing surfactant having crystal growth inhibiting properties; or i) adding a stabilization system having crystal growth inhibiting properties to said liquid composition, and / or e) formulating the composition to have a viscosity of at least 500 cP; thereby improving the stability of said composition comprising said compound of formula I.

24. Formula I: 【Chemistry 6】 Polyalkylene oxide polyaromatic compounds for controlling the solubility and / or degradation of the compounds of the present invention Use of at least one stabilizing surfactant having a aryl ether structure.

25. Formula I: 【Chemistry 7】 1. A method for preparing a concentrated suspension (SC) composition comprising a compound of formula (I), The method comprises: (1) Mixing an agriculturally acceptable inert additive with an aqueous liquid carrier to obtain a premix. Step, (2) adding the compound of formula I to the premix obtained in step (1) to form a mixture obtaining, (3) milling the mixture obtained in step (2) to obtain the desired composition. A method comprising:

26. Formula I: 【Chemistry 8】 1. A method for preparing a suspoemulsion (SE) composition comprising the steps of: The method comprises: (1) Mixing an agriculturally acceptable inert additive with an aqueous liquid carrier to obtain a premix. Step, (2) The compound of formula I and at least one adjuvant obtained in step (1) are adding to the premix to obtain a mixture; and (3) milling the mixture obtained in step (2) to obtain the desired composition. A method comprising:

27. Formula I: 【Chemistry 9】 1. A method for preparing an oil dispersion (OD) composition comprising the compound of The method comprises: (1) Mixing an agriculturally acceptable inert additive with a non-aqueous liquid carrier to obtain a premix. Step (2) adding the compound of formula I to the premix obtained in step (1) to form a mixture obtaining, (3) milling the mixture obtained in step (2) to obtain the desired composition. A method comprising:

28. Formula I: 【Chemistry 10】 1. A method for preparing an emulsion concentrate (EC) composition comprising the compound of The method comprises: (1) Mixing an agriculturally acceptable inert additive with a non-aqueous liquid carrier to obtain a premix. Step (2) adding the compound of formula I to the premix obtained in step (1) to form a mixture obtaining, (3) filtering the solution of step (2) to obtain the desired composition. A method comprising:

29. The composition or mixture according to any one of claims 1 to 16 is used to produce a plant. (i) controlling or preventing fungal infestation of plants; or (ii) A method for the protection of plants from fungal infestation.

30. A composition or mixture according to any one of claims 1 to 16 is applied to the seeds or seedlings of a plant. Treating plant seeds or seedlings to produce plants resistant to fungal infestation, including by spreading How to place it.

31. Applying a composition or mixture according to any one of claims 1 to 16 to the nursery environment.

13. A method for protecting a plant from fungal infestation, comprising:

32. The seeds of the plant are treated with a composition or mixture according to any one of claims 1 to 16. , plants resistant to fungal invasion.

33. A plant seed or seedling is treated with a composition or mixture according to any one of claims 1 to 16. The seed or seedling of a plant adapted to produce a plant resistant to fungal infestation is placed in a culture medium.

34. A package comprising a composition or mixture according to any one of claims 1 to 16.

35. Use of a mixture according to any one of claims 11 to 16 for the preparation of a fungicidal composition. 。

36. (i) the control and / or prevention of fungal infestation in plants, and / or (ii) the prevention and / or treatment of plants and / or for use in controlling and / or preventing fungal diseases in soil.

17. The composition or mixture according to any one of claims 1 to 16, or (i) a fungus on a plant. (ii) the control and / or prevention of infestations of plants and / or soil The method according to any one of claims 1 to 16 for controlling and / or preventing fungal diseases of Use of the composition or mixture.

37. (a) controlling and / or preventing fungal pathogen infestation of plants, and / or (b). For the control and / or prevention of plant and / or soil fungal diseases, compounds of the formula (I): 【Chemistry 11】 and (i) polyalkylene oxide alkyl ethers, (ii) siloxane polyalkylene oxide copolymers; (iii) esters of fatty acids, (iv) vinylpyrrolidone and its derivatives, and (v) Sugar surfactant Use of at least one adjuvant selected from the group consisting of:

38. (a) controlling and / or preventing fungal pathogen infestation of plants, and / or (b). For use in the control and / or prevention of fungal diseases of plants and / or soil of formula (I): 【Chemistry 12】 and (i) polyalkylene oxide alkyl ethers, (ii) siloxane polyalkylene oxide copolymers; (iii) esters of fatty acids, (iv) vinylpyrrolidone and its derivatives, and (v) Sugar surfactant At least one adjuvant selected from the group consisting of:

39. Formula (I): 【Chemistry 13】 To improve the biological activity of the compound of (i) polyalkylene oxide alkyl ethers, (ii) siloxane polyalkylene oxide copolymers; (iii) esters of fatty acids, (iv) vinylpyrrolidone and its derivatives, and (v) Sugar surfactant Use of at least one adjuvant selected from the group consisting of:

40. Formula (I): 【Chemistry 14】 For use in improving the biological activity of a compound of (i) polyalkylene oxide alkyl ethers, (ii) siloxane polyalkylene oxide copolymers; (iii) esters of fatty acids, (iv) vinylpyrrolidone and its derivatives, and (v) Sugar surfactant An adjuvant selected from the group consisting of:

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