Mixtures and composition comprising thereof

Abstract

The present subject matter relates to mixture and compositions comprising (a) one or more solid forms of flumetylsulforim, and (b) one or more of Compound I.

Description

MIXTURES AND COMPOSITION COMPRISING THEREOFField of the Invention

[0001] The present subject matter relates to multi-component, associations, combinations, mixtures, admixes, solutions, emulsions, granules, dispersions, etc. comprising: (a) one or more solid forms of flumetylsulforim, and (b) one or more of Compound I selected from: (1) 4-(Hydroxymethyl)benzene-l-sulfinic acid, (2) 5-fluoro-l-((4-(hydroxymethyl)phenyl)sulfonyl)-4-imino-3-methyl-3,4-dihydropyrimidin-2(lH)-one, (3) 2,4- Pyrimidinedione, 5-fluoro-3-methyl-l-[(4-methylphenyl)sulfonyl], (4) (E)-2-fluoro-3-lmino-3- (methylamino)-l-(p-tolylsulfonylamino)l-propene and (5) [p-(3-Methylureidosulfonyl)phenyl] methanol, and compositions comprising thereof.Background of the Invention

[0002] Fungicides are compounds of natural or synthetic origin, which act to protect plants against damage caused by fungi. Current methods of agriculture rely heavily on the use of fungicides. In fact, some crops cannot be grown usefully without the use of fungicides. Using fungicides allows a grower to increase the yield and the quality of the crop, and consequently, increase the value of the crop. In most situations, the increase in value of the crop is worth at least three times the cost of the use of the fungicide. Flumetylsulforim having the chemical name 5-Fluoro-4-imino-3-methyl-l-tosyl-3,4-dihydropyrimidin-2(lH)-one and the structure I is a compound which provides control of a variety of pathogens affecting economically important crops including, but not limited to, the causal agent of leaf blotch in wheat, Zymoseptoria tritici (SEPTTR) and fungi of the classes ascomycetes and basidiomycetes.structure I.

[0003] Flumetylsulforim is related with formation of different compounds and there is a need for tools for analyzing Flumetylsulforim.

[0004] Patent application PCT / IB2024 / 053567 disclosed compound I of the present invention, that was used, inter alia, as a standard for an efficient, fast and simple tool for determining purity and / or metabolite profile of Flumetylsulforim.Summary of the Invention

[0005] The present invention provides mixtures comprising: (a) one or more solid forms of flumetylsulforim, and (b) one or more Compound I, wherein compound I is selected from: (1) 4-(Hydroxymethyl)benzene-l-sulfinic acid, (2) 5-fluoro-l-((4-(hydroxymethyl)phenyl)sulfonyl)-4-imino-3-methyl-3,4-dihydropyrimidin-2(lH)-one, (3) 2,4- Pyrimidinedione, 5-fluoro-3-methyl-l-[(4-methylphenyl)sulfonyl], (4) (E)-2-fluoro-3-lmino-3- (methylamino)-l-(p-tolylsulfonylamino)l-propene and (5) [p-(3-Methylureidosulfonyl)phenyl] methanol.

[0006] The present invention provides compositions comprising: (a) one or more solid forms of flumetylsulforim, and (b) one or more Compound I, wherein compound I is selected from: (1) 4-(Hydroxymethyl)benzene-l-sulfinic acid, (2) 5-fluoro-l-((4-(hydroxymethyl)phenyl)sulfonyl)-4-imino-3-methyl-3,4-dihydropyrimidin-2(lH)-one, (3) 2,4- Pyrimidinedione, 5-fluoro-3-methyl-l-[(4-methylphenyl)sulfonyl], (4) (E)-2-fluoro-3-lmino-3- (methylamino)-l-(p-tolylsulfonylamino)l-propene and (5) [p-(3-Methylureidosulfonyl)phenyl] methanol.

[0007] The present invention provides use of the Compound I as reference standard for determining purity and / or metabolite profile of solid form of Flumetylsulforim.

[0008] The present invention provides use of Compound I as reference standard for determining the purity of a composition comprising solid form Flumetylsulforim.

[0009] The present invention provides use of Compound I as a reference standard to test for its presence and / or quantity in a solid form of solid form of Flumetylsulforim.

[0010] The present invention provides use of Compound I as a reference standard to test for its presence and / or quantity in a composition.

[0011] The present invention provides use of Compound I as reference standard to test for its presence and / or quantity at a locus where solid form of Flumetylsulforim was applied.

[0012] The present invention provides use of Compound I as reference standard to test for its presence and / or quantity in a plant to which solid form of Flumetylsulforim was applied.Detailed Description of the InventionDefinitions

[0013] Prior to setting forth the present subject matter in detail, it may be helpful to provide definitions of certain terms to be used herein. Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this general inventive concept belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that is consistent with their meaning in the context of the relevant art and the present disclosure, and will not be interpreted in an idealized or overly formal sense unless expressly so defined herein.

[0014] Throughout the application, descriptions of various embodiments use the term "comprising"; however, it will be understood by one of skill in the art, that in some specific instances, an embodiment can alternatively be described using the language "consisting essentially of" or "consisting of."

[0015] The term "a" or "an" as used herein includes the singular and the plural, unless specifically stated otherwise. Therefore, the terms "a," "an" or "at least one" can be used interchangeably in this application, to be clear that the use of terms "a," or "an" does not intend to convey the absence of multiples unless the context requires it.

[0016] The term "about" herein specifically includes ±10% from the indicated values in the range. In addition, the endpoints of all ranges directed to the same component or property herein are inclusive of the endpoints, are independently combinable, and include all intermediate points and ranges.

[0017] It is understood that where a parameter range is provided, all integers within that range, and tenths thereof, are also provided by the invention as if the integers and tenths thereof are expressly described herein. For example, "5 g / ha to 120 g / ha" includes 5.0 g / ha, 5.1 g / ha, 5.2 g / ha, 5.3 g / ha, 5.4 g / ha, etc. up to 120 g / ha.

[0018] As used herein, the term "plant" includes reference to the whole plant, plant organ (e.g., leaves, stems, twigs, roots, trunks, limbs, shoots, fruits etc.), plant cells, and propagation material of the plant.

[0019] As used herein the term "plant" includes reference to agricultural crops include field crops (soybean, maize, wheat, rice, etc.), vegetable crops (potatoes, cabbages, etc.) and fruits (peach, etc.).

[0020] As used herein, the terms "composition" and "formulation" are interchangeable.

[0021] Flumetylsulforim is related with formation of compound I selected from a group consisting of (1) 4-(Hydroxymethyl)benzene-l-sulfinic acid, (2) 5-fluoro-l-((4- (hydroxymethyl)phenyl)sulfonyl)-4-imino-3-methyl-3,4-dihydropyrimidin-2(lH)-one, (3) 2,4- Pyrimidinedione, 5-fluoro-3-methyl-l-[(4-methylphenyl)sulfonyl], (4) (E)-2-fluoro-3-lmino-3-(methylamino)-l-(p-tolylsulfonylamino)l-propene and (5)Methylureidosulfonyl)phenyl] methanol.

[0022] Solid form of flumetylsulforim includes all solid forms thereof including, but not limited to, amorphous, crystalline, solvate or hydrate. Solid forms of Flumetylsulforim are disclosed in PCT International Application Publication No. WO 2019 / 038583 Al, published February 28, 2019, WO 2022 / 234487, published November 10, 2022, WO 2015 / 103142 and WO 2015 / 103144 the entire content of which is hereby incorporated by reference.

[0023] In some embodiments, the term "solid form of flumetylsulforim" includes solid flumetylsulforim compounds as well as compounds that were solids before they were dissolved, such as in the case of EC formulations.

[0024] In some embodiments, solid form of flumetylsulforim is used for formulating a composition as described herein.

[0025] Analyzing Flumetylsulforim was found to be challenging, and identification and characterization of compound I using a standard provides efficient, fast and simple tool for determining purity and / or metabolite profile of Flumetylsulforim.

[0026] The present invention concerns mixture comprising (a) one or more solid forms of flumetylsulforim and (b) at least one compound I selected from a group consisting of (1) 4- (Hydroxymethyl)benzene-l-sulfinic acid, (2) 5-fluoro-l-((4-(hydroxymethyl)phenyl)sulfonyl)- 4-imino-3-methyl-3,4-dihydropyrimidin-2(lH)-one, (3) 2,4-Pyrimidinedione, 5-fluoro-3- methyl-l-[(4-methylphenyl)sulfonyl], (4) (E)-2-fluoro-3-lmino-3-(methylamino)-l-(p- tolylsulfonylamino)l-propene and (5) [p-(3-Methylureidosulfonyl)phenyl]methanol.

[0027] The solid form of flumetylsulforim refers to any solid form including but not limited to amorphous, crystalline, solvate or hydrate.

[0028] The solid form of flumetylsulforim includes crystalline forms of the compound of Formula I.

[0029] In some embodiments, the crystalline form is an anhydrous crystalline form. In some embodiments, the anhydrous crystalline form is a polymorph. In some embodiments, the anhydrous crystalline form is a pseudopolymorph.

[0030] In some embodiments, the crystalline form is a hydrate.

[0031] In some embodiments, the crystalline form is a solvate. In some embodiments, the solvate contains 1,4-dioxane. In some embodiments, the solvate contains tetrahydrofuran. In some embodiments, the solvate contains ethyl acetate.

[0032] In some embodiments, the crystalline polymorphic form (Form I) exhibits an X-ray powder diffraction pattern having characteristic peaks at 2-theta angles of 9.08, 10.98, 14.05, 17.51, 18.75, 21.63, 23.33, 24.70, 24.83, 25.37, 26.51 and 29.23. In some embodiments, the powder X-ray diffraction pattern of Form I comprises characteristic peaks at 2-theta angles of 14.05, 17.51, 18.75, 21.63 and 26.51. In some embodiments, the powder X-ray diffractionpattern of Form I comprises characteristic peaks at 2-theta angles of 14.05, 17.51, 18.75 and 21.63.

[0033] In some embodiments, the crystalline polymorphic form (Form I) is characterized by decomposition beginning at a temperature greater than 210°C.

[0034] In some embodiments, the crystalline polymorphic form (Form I) exhibits a Differential Scanning Calorimetry (DSC) thermogram characterized by a predominant endothermic peak with a peak temperature of about 160°C, a predominant endothermic peak with an onset temperature of about 159°C, and a predominant endothermic peak with a melting enthalpy of about 110 J / g.

[0035] In some embodiments, the crystalline polymorphic form (Form II) exhibits an X-ray powder diffraction pattern having characteristic peaks at 2-theta angles of 7.98, 9.20, 9.96, 11.88, 15.99, 18.49, 21.23, 22.33, 22.59, 26.73. In some embodiments, the powder X-ray diffraction pattern of Form II comprises characteristic peaks at 2-theta angles of 9.20, 9.96, 11.88, 22.33 and 22.59. In some embodiments, the powder X-ray diffraction pattern of Form II comprises characteristic peaks at 2-theta angles of 9.20, 11.88, 22.33 and 22.59.

[0036] In some embodiments, the crystalline polymorphic form (Form II) exhibits a TG-FTIR thermogram characterized by decomposition beginning at a temperature greater than 210°C.

[0037] In some embodiments, the crystalline polymorphic form (Form II) exhibits a Differential Scanning Calorimetry (DSC) thermogram characterized by a predominant endothermic peak with a peak temperature of about 157°C, a predominant endothermic peak with an onset temperature of about 156°C, and a predominant endothermic peak with a melting enthalpy of about 112 J / g.

[0038] In some embodiments, the crystalline hydrate form (Hydrate) exhibits an X-ray powder diffraction pattern having characteristic peaks at 2-theta 5.34, 7.48, 10.68, 16.05, 21.79, 22.99, 23.19, 24.95, 26.95, 27.63. In some embodiments, the powder X-ray diffraction pattern of Hydrate comprises characteristic peaks at 2-theta angles of 5.34, 7.48, 10.68, 16.05 and 21.79. In some embodiments, the powder X-ray diffraction pattern of Hydrate comprises characteristic peaks at 2-theta angles of 5.34, 7.48, 10.68 and 16.05.

[0039] In some embodiments, the crystalline hydrate form (Hydrate) exhibits a TG-FTIR thermogram characterized by decomposition beginning at a temperature greater than 190 °C.

[0040] In some embodiments, the crystalline hydrate form (Hydrate) exhibits a Differential Scanning Calorimetry (DSC) thermogram characterized by a predominant endothermic peak with a peak temperature of about 139.5°C, a predominant endothermic peak with an onset temperature of about 139°C, and a predominant endothermic peak with a melting enthalpy of about 115 J / g, wherein the DSC is measured in a sealed pan.

[0041] In some embodiments, the crystalline hydrate form (Hydrate) exhibits a Differential Scanning Calorimetry (DSC) thermogram characterized by a predominant endothermic peak with a peak temperature of about 160°C, a predominant endothermic peak with an onsettemperature of about 159°C, and a predominant endothermic peak with a melting enthalpy of about 98 J / g, wherein the DSC is measured in an open pan.

[0042] In some embodiments, the crystalline solvate form (Form S5) exhibits an X-ray powder diffraction pattern having characteristic peaks at 2-theta 5.42, 7.50, 10.06, 10.82, 12.80, 16.91, 21.55, 23.13, 24.83, 26.81, 27.77. In some embodiments, the powder X-ray diffraction pattern of Form S5 comprises characteristic peaks at 2-theta angles of 5.42, 7.50, 10.06, 10.82, and 16.91. In some embodiments, the powder X-ray diffraction pattern of Form S5 comprises characteristic peaks at 2-theta angles of 5.42, 7.50, 10.82 and 16.91.

[0043] In some embodiments, the crystalline solvate form (Form 55) exhibits a TG-FTIR thermogram characterized by decomposition beginning at a temperature greater than 180°C.

[0044] In some embodiments, the crystalline solvate form (Form 58) exhibits an X-ray powder diffraction pattern, having characteristic peaks at 2-theta 4.7, 5.00, 5.38, 6.26, 9.66, 15.93, 21.05, 23.97, 24.69. In some embodiments, the powder X-ray diffraction pattern of Form 58 comprises characteristic peaks at 2-theta angles of 4.7, 5.00, 5.38, 6.26, 9.66 and 23.97. In some embodiments, the powder X-ray diffraction pattern of Form 58 comprises characteristic peaks at 2-theta angles of 4.7, 5.00, 9.66 and 23.97.

[0045] In some embodiments, the crystalline solvate form (Form 58) exhibits a TG-FTIR thermogram characterized by decomposition beginning at a temperature greater than 180°C.

[0046] In some embodiments, the crystalline solvate form (Form 51) exhibits an X-ray powder diffraction pattern having characteristic peaks at 2-theta 5.34, 7.48, 10.10, 10.68, 12.90, 16.07, 21.83, 23.09, 24.91, 26.93. In some embodiments, the powder X-ray diffraction pattern of Form 51 comprises characteristic peaks at 2-theta angles of 5.34, 7.48, and 10.68. In some embodiments, the powder X-ray diffraction pattern of Form 51 comprises characteristic peaks at 2-theta angles of 5.34, 7.48, 10.68 and 21.83. In some embodiments, the powder X-ray diffraction pattern of Form 51 comprises characteristic peaks at 2-theta angles of 5.34, 7.48, 10.68, 16.07 and 21.83.

[0047] In some embodiments, the crystalline solvate form (Form 51) exhibits a TG-FTIR thermogram characterized by decomposition beginning at a temperature greater than 200 °C.

[0048] In some embodiments, the crystalline solvate form (Form III) exhibits an X-ray powder diffraction pattern having characteristic peaks at 4.5, 5.1, 9.1, 10.1, 22.4, 23.5 ± 0.2 deg 2- theta. In another embodiment the X-ray powder diffraction pattern of Form III comprises characteristic peaks at 4.5, 5.1, 9.1, 10.1, 11.9, 14.2, 16.1, 22.4, 23.5 ± 0.2 deg 2-theta.

[0049] In some embodiments, Form III is anhydrous based on TGA analysis which shows that no significant weight loss occurs up to 200 deg. The DSC melting event occurs between about 155-158 deg.

[0050] In some embodiments, the crystalline solvate form (Form Illa) exhibits an X-ray powder diffraction pattern having characteristic peaks at 4.5, 5.0, 9.3, 10.0, 22.3, 22.6 ± 0.2 deg 2-theta. In another embodiment the X-ray powder diffraction pattern of Form Illacomprises characteristic peaks at 4.5, 5.0, 9.3, 10.0, 11.9, 14.2, 16.0, 22.3, 22.6, 25.3 ± 0.2 deg 2-theta.

[0051] Form Illa is anhydrous, based on TGA analysis, which shows that no significant weight loss occurs up to 200 deg.

[0052] In some embodiments, the crystalline solvate form (Form 02) exhibits an X-ray powder diffraction pattern having characteristic peaks at 7.5, 14.3, 15.8, 22.4, 24.7 ± 0.2 deg 2-theta. In another embodiment, the X-ray powder diffraction pattern of Form 02 comprises characteristic peaks at 7.5, 11.9, 14.3, 15.8, 18.7, 22.4, 24.7, 27.4, 31.1 ± 0.2 deg 2-theta.

[0053] Form 02 is anhydrous based on TGA analysis, which shows that no significant weight loss occurs up to 200 deg. The DSC melting event y occurs between about 155-158 deg.

[0054] In some embodiments, the crystalline solvate form (Form 01) exhibits an X-ray powder diffraction pattern having characteristic peaks at 5.1, 6.4, 7.5, 10.3, 16.1 ± 0.2 deg 2-theta. In another embodiment, the X-ray powder diffraction pattern of Form 01 comprises characteristic peaks at 5.1, 6.4, 7.5, 10.3, 12.2, 13.4, 14.9, 16.1, 18.4 ± 0.2 deg 2-theta.

[0055] The DSC melting event y occurs between about 155-165 deg.

[0056] In some embodiments, the solid form of flumetylsulforim is the solid obtained from the process disclosed in international application publication no. WO 2015 / 103142.

[0057] In some embodiments, the solid form of flumetylsulforim is the solid obtained from the process disclosed in international application publication no. WO 2015 / 103144.

[0058] In some embodiments, the solid form of flumetylsulforim has a powder X-ray diffraction pattern substantially in accordance with the pattern of the solid obtained from the process disclosed in international application publication no. WO 2015 / 103142.

[0059] In some embodiments, the X-ray powder diffraction patterns of the solid form of flumetylsulforim and the solid obtained from the process disclosed in international application publication WO 2015 / 103142 share at least 5, 6, 7, 8, 9, or 10 peaks.

[0060] In some embodiments, the solid form of flumetylsulforim has a powder X-ray diffraction pattern substantially in accordance with the pattern of the solid obtained from the process disclosed in international application publication no. WO 2015 / 103144.

[0061] In some embodiments, the X-ray powder diffraction patterns of the solid form of flumetylsulforim and the solid obtained from the process disclosed in international application publication WO 2015 / 103144 share at least 5, 6, 7, 8, 9, or 10 peaks.

[0062] In some embodiments, the purity of the solid form of the flumetylsulforim is at least 95%, 96%, or 97%.

[0063] In some embodiments, the mixture comprises compound I selected from a group consisting of (1) 4-(Hydroxymethyl)benzene-l-sulfinic acid, (2) 5-fluoro-l-((4-(hydroxymethyl)phenyl)sulfonyl)-4-imino-3-methyl-3,4-dihydropyrimidin-2(lH)-one, (3) 2,4- Pyrimidinedione, 5-fluoro-3-methyl-l-[(4-methylphenyl)sulfonyl], (4) (E)-2-fluoro-3-lmino-3- (methylamino)-l-(p-tolylsulfonylamino)l-propene and (5) [p-(3-Methylureidosulfonyl)phenyl]methanol and Form I described herein.

[0064] In some embodiments, the mixture comprises a compound I selected from a group consisting of (1) 4-(Hydroxymethyl)benzene-l-sulfinic acid, (2) 5-fluoro-l-((4- (hydroxymethyl)phenyl)sulfonyl)-4-imino-3-methyl-3,4-dihydropyrimidin-2(lH)-one, (3) 2,4- Pyrimidinedione, 5-fluoro-3-methyl-l-[(4-methylphenyl)sulfonyl], (4) (E)-2-fluoro-3-lmino-3- (methylamino)-l-(p-tolylsulfonylamino)l-propene and (5) [p-(3-Methylureidosulfonyl)phenyl]methanol and Form II described herein.

[0065] In some embodiments, the mixture comprises compound I selected from a group consisting of (1) 4-(Hydroxymethyl)benzene-l-sulfinic acid, (2) 5-fluoro-l-((4- (hydroxymethyl)phenyl)sulfonyl)-4-imino-3-methyl-3,4-dihydropyrimidin-2(lH)-one, (3) 2,4- Pyrimidinedione, 5-fluoro-3-methyl-l-[(4-methylphenyl)sulfonyl], (4) (E)-2-fluoro-3-lmino-3- (methylamino)-l-(p-tolylsulfonylamino)l-propene and (5) [p-(3-Methylureidosulfonyl)phenyl]methanol and Form III described herein.

[0066] In some embodiments, the mixture comprises compound I selected from a group consisting of (1) 4-(Hydroxymethyl)benzene-l-sulfinic acid, (2) 5-fluoro-l-((4- (hydroxymethyl)phenyl)sulfonyl)-4-imino-3-methyl-3,4-dihydropyrimidin-2(lH)-one, (3) 2,4- Pyrimidinedione, 5-fluoro-3-methyl-l-[(4-methylphenyl)sulfonyl], (4) (E)-2-fluoro-3-lmino-3- (methylamino)-l-(p-tolylsulfonylamino)l-propene and (5) [p-(3-Methylureidosulfonyl)phenyl]methanol and Hydrate described herein.

[0067] In some embodiments, the mixture comprises compound I selected from a group consisting of (1) 4-(Hydroxymethyl)benzene-l-sulfinic acid, (2) 5-fluoro-l-((4- (hydroxymethyl)phenyl)sulfonyl)-4-imino-3-methyl-3,4-dihydropyrimidin-2(lH)-one, (3) 2,4- Pyrimidinedione, 5-fluoro-3-methyl-l-[(4-methylphenyl)sulfonyl], (4) (E)-2-fluoro-3-lmino-3- (methylamino)-l-(p-tolylsulfonylamino)l-propene and (5) [p-(3-Methylureidosulfonyl)phenyl]methanol and Form 55 described herein.

[0068] In some embodiments, the mixture comprises compound I selected from a group consisting of (1) 4-(Hydroxymethyl)benzene-l-sulfinic acid, (2) 5-fluoro-l-((4- (hydroxymethyl)phenyl)sulfonyl)-4-imino-3-methyl-3,4-dihydropyrimidin-2(lH)-one, (3) 2,4- Pyrimidinedione, 5-fluoro-3-methyl-l-[(4-methylphenyl)sulfonyl], (4) (E)-2-fluoro-3-lmino-3- (methylamino)-l-(p-tolylsulfonylamino)l-propene and (5) [p-(3-Methylureidosulfonyl)phenyl]methanol and Form 58 described herein.

[0069] In some embodiments, the mixture comprises compound I selected from a group consisting of (1) 4-(Hydroxymethyl)benzene-l-sulfinic acid, (2) 5-fluoro-l-((4- (hydroxymethyl)phenyl)sulfonyl)-4-imino-3-methyl-3,4-dihydropyrimidin-2(lH)-one, (3) 2,4- Pyrimidinedione, 5-fluoro-3-methyl-l-[(4-methylphenyl)sulfonyl], (4) (E)-2-fluoro-3-lmino-3- (methylamino)-l-(p-tolylsulfonylamino)l-propene and (5) [p-(3-Methylureidosulfonyl)phenyl]methanol and Form 51 described herein.

[0070] In some embodiments, the mixture comprises compound I selected from a group consisting of (1) 4-(Hydroxymethyl)benzene-l-sulfinic acid, (2) 5-fluoro-l-((4- (hydroxymethyl)phenyl)sulfonyl)-4-imino-3-methyl-3,4-dihydropyrimidin-2(lH)-one, (3) 2,4- Pyrimidinedione, 5-fluoro-3-methyl-l-[(4-methylphenyl)sulfonyl], (4) (E)-2-fluoro-3-lmino-3- (methylamino)-l-(p-tolylsulfonylamino)l-propene and (5) [p-(3-Methylureidosulfonyl)phenyl]methanol and Form III described herein.

[0071] In some embodiments, the mixture comprises compound I selected from a group consisting of (1) 4-(Hydroxymethyl)benzene-l-sulfinic acid, (2) 5-fluoro-l-((4- (hydroxymethyl)phenyl)sulfonyl)-4-imino-3-methyl-3,4-dihydropyrimidin-2(lH)-one, (3) 2,4- Pyrimidinedione, 5-fluoro-3-methyl-l-[(4-methylphenyl)sulfonyl], (4) (E)-2-fluoro-3-lmino-3- (methylamino)-l-(p-tolylsulfonylamino)l-propene and (5) [p-(3-Methylureidosulfonyl)phenyl]methanol and Form Illa described herein.

[0072] In some embodiments, the mixture comprises compound I selected from a group consisting of (1) 4-(Hydroxymethyl)benzene-l-sulfinic acid, (2) 5-fluoro-l-((4- (hydroxymethyl)phenyl)sulfonyl)-4-imino-3-methyl-3,4-dihydropyrimidin-2(lH)-one, (3) 2,4- Pyrimidinedione, 5-fluoro-3-methyl-l-[(4-methylphenyl)sulfonyl], (4) (E)-2-fluoro-3-lmino-3- (methylamino)-l-(p-tolylsulfonylamino)l-propene and (5) [p-(3-Methylureidosulfonyl)phenyl]methanol and Form 02 described herein.

[0073] In some embodiments, the mixture comprises compound I selected from a group consisting of (1) 4-(Hydroxymethyl)benzene-l-sulfinic acid, (2) 5-fluoro-l-((4- (hydroxymethyl)phenyl)sulfonyl)-4-imino-3-methyl-3,4-dihydropyrimidin-2(lH)-one, (3) 2,4- Pyrimidinedione, 5-fluoro-3-methyl-l-[(4-methylphenyl)sulfonyl], (4) (E)-2-fluoro-3-lmino-3- (methylamino)-l-(p-tolylsulfonylamino)l-propene and (5) [p-(3-Methylureidosulfonyl)phenyl]methanol and Form 01 described herein.

[0074] In some embodiments, the mixture comprises compound I selected from a group consisting of (1) 4-(Hydroxymethyl)benzene-l-sulfinic acid, (2) 5-fluoro-l-((4- (hydroxymethyl)phenyl)sulfonyl)-4-imino-3-methyl-3,4-dihydropyrimidin-2(lH)-one, (3) 2,4- Pyrimidinedione, 5-fluoro-3-methyl-l-[(4-methylphenyl)sulfonyl], (4) (E)-2-fluoro-3-lmino-3- (methylamino)-l-(p-tolylsulfonylamino)l-propene and (5) [p-(3-Methylureidosulfonyl)phenyl]methanol and a solid form of flumetylsulforim having a powder X-ray diffraction pattern substantially in accordance with the pattern of the solid obtained from the process disclosed in international application publication No. WO 2015 / 103142.

[0075] In some embodiments, the mixture comprises compound I selected from a group consisting of (1) 4-(Hydroxymethyl)benzene-l-sulfinic acid, (2) 5-fluoro-l-((4- (hydroxymethyl)phenyl)sulfonyl)-4-imino-3-methyl-3,4-dihydropyrimidin-2(lH)-one, (3) 2,4- Pyrimidinedione, 5-fluoro-3-methyl-l-[(4-methylphenyl)sulfonyl], (4) (E)-2-fluoro-3-lmino-3- (methylamino)-l-(p-tolylsulfonylamino)l-propene and (5) [p-(3-Methylureidosulfonyl)phenyl]methanol and a solid form of flumetylsulforim having a powder X-ray diffraction pattern substantially in accordance with the pattern of the solid obtained from the process disclosed in international application publication No. WO 2015 / 103144.

[0076] In some embodiments, compound I is 4-(Hydroxymethyl)benzene-l-sulfinic acid.

[0077] 4-(Hydroxymethyl)benzene-l-sulfinic acid has the following structure A:

[0078] 4-(Hydroxymethyl)benzene-l-sulfinic acid has an NMR spectrum substantially in accordance with the spectrum as shown in figure 1 as described in the international application No. PCT / IB2024 / 053567 the content of which is incorporated by reference.

[0079] In some embodiments, the compound I having structure A may be prepared as disclosed in the following scheme 1:

[0080] In some embodiments, compound I is 5-fluoro-l-((4- (hydroxymethyl)phenyl)sulfonyl)-4-imino-3-methyl-3,4-dihydropyrimidin-2(lH)-one.

[0081] 5-fluoro-l-((4-(hydroxymethyl)phenyl)sulfonyl)-4-imino-3-methyl-3,4- dihydropyrimidin-2(lH)-one has the following structure B:

[0082] 5-fluoro-l-((4-(hydroxymethyl)phenyl)sulfonyl)-4-imino-3-methyl-3,4- dihydropyrimidin-2(lH)-one has an NMR spectrum substantially in accordance with the spectrum as shown in figure 3 as described in the international application No. PCT / IB2024 / 053567 the content of which is incorporated by reference.

[0083] In some embodiments, compound having structure B may be prepared as disclosed in the following scheme 2:

[0084] In some embodiments, compound I is 2,4-Pyrimidinedione, 5-fluoro-3-methyl-l-[(4- methylphenyl)sulfonyl].

[0085] 2,4-Pyrimidinedione, 5-fluoro-3-methyl-l-[(4-methylphenyl)sulfonyl] has the following structure C:

[0086] 2,4-Pyrimidinedione, 5-fluoro-3-methyl-l-[(4-methylphenyl)sulfonyl] has a mass spectrum substantially in accordance with the spectrum as shown in figure 5 as described in the international application No. PCT / IB2024 / 053567 the content of which is incorporated by reference.

[0087] Any one or any combination of the peaks fragments shown in figure 5 may be used to identify 2,4-Pyrimidinedione, 5-fluoro-3-methyl-l-[(4-methylphenyl)sulfonyl].

[0088] 2,4-Pyrimidinedione, 5-fluoro-3-methyl-l-[(4-methylphenyl)sulfonyl] may be identified using one of the peaks fragments shown in figure 5. For example, 2,4- Pyrimidinedione, 5-fluoro-3-methyl-l-[(4-methylphenyl)sulfonyl] has characteristic peak fragment in mass spectroscopy [M+H]+ 299 m / z.

[0089] 2,4-Pyrimidinedione, 5-fluoro-3-methyl-l-[(4-methylphenyl)sulfonyl] may be identified using two of the peaks shown in figure 5 as described in the international application No. PCT / IB2024 / 053567 the content of which is incorporated by reference.

[0090] 2,4-Pyrimidinedione, 5-fluoro-3-methyl-l-[(4-methylphenyl)sulfonyl] may be identified using three of the peaks fragments shown in figure 5 as described in the international application No. PCT / IB2024 / 053567 the content of which is incorporated by reference.

[0091] 2,4-Pyrimidinedione, 5-fluoro-3-methyl-l-[(4-methylphenyl)sulfonyl] may be identified using four of the peaks fragments shown in figure 5 as described in the international application No. PCT / IB2024 / 053567 the content of which is incorporated by reference.

[0092] For example, 2,4-Pyrimidinedione, 5-fluoro-3-methyl-l-[(4-methylphenyl)sulfonyl] has characteristic peak fragment in mass spectroscopy [M+H]+ 299 m / z and at least one fragments and adduct of the molecule are in 113.0712 m / z (C5H9N2O), 145.0408 m / z (C5H6FN2O2) or 316.0761 m / z (C12H15FN3O4S, [M+NH4] + ).

[0093] For example, 2,4-Pyrimidinedione, 5-fluoro-3-methyl-l-[(4-methylphenyl)sulfonyl] has characteristic peak in mass spectroscopy [M+H]+ 299 m / z and at least one fragments and adduct of the molecule are in 113.0712 m / z (C5H9N2O), 145.0408 m / z (C5H6FN2O2) and 316.0761 m / z (C12H15FN3O4S, [M+NH4] + ).

[0094] In some embodiments, compound I having structure C may be prepared as disclosed in the following scheme 3:

[0095] In some embodiments, compound I is E)-2-fluoro-3-lmino-3-(methylamino)-l-(p- tolylsulfonylamino)l-propene.

[0096] (E)-2-fluoro-3-lmino-3-(methylamino)-l-(p-tolylsulfonylamino)l-propene has the following structure D:

[0097] (E)-2-fluoro-3-lmino-3-(methylamino)-l-(p-tolylsulfonylamino)l-propene has an NMR spectrum substantially in accordance with the spectrum in figure 6 as described in the international application No. PCT / IB2024 / 053567 the content of which is incorporated by reference.

[0098] In some embodiments, compound I having structure D may be prepared as disclosed in the following scheme 4:

[0099] In some embodiments, compound I is [p-(3-Methylureidosulfonyl)phenyl]methanol.

[0100] [p-(3-Methylureidosulfonyl)phenyl]methanol has the following structure E:

[0101] [p-(3-Methylureidosulfonyl)phenyl]methanol has an NMR spectrum substantially in accordance with the spectrum of figure 8 as described in the international application No. PCT / IB2024 / 053567 the content of which is incorporated by reference.

[0102] In some embodiments, compound I having structure E may be prepared as disclosed in the following scheme 5:

[0103] Compound I can be prepared for example as described in the international application No. PCT / IB2024 / 053567, the entire content of which is hereby incorporated by reference.

[0104] In some embodiments, compound I is produced synthetically.

[0105] In some embodiments, compound I is free of plant material and / or biological material (such as tissue).

[0106] Compound(s) I may be present as impurities in a batch of flumetylsulforim or in a mixture or composition comprising solid form of flumetylsulforim as described herein. The identification of compound(s) I, including the compounds described above and mixtures thereof, allows each of these compounds and mixtures to be used as reference standard for quality control of batches of flumetylsulforim or mixtures or compositions of solid forms of flumetylsulforim as described herein. In particular, the identification of compounds I and mixtures thereof as described herein, including the compounds and mixtures described above, allows for the development of a reference standard profile, including but not limited to NMR profile. Any machine can be calibrated for the detection of these compounds to screen batches of solid forms of flumetylsulforim or mixtures or compositions comprising solid forms of flumetylsulforim and for presence of these compounds and amounts thereof.

[0107] Compound(s) I may be present as impurities in a batch of solid forms of flumetylsulforim or in a mixture or composition comprising solid forms of flumetylsulforim. Flumetylsulforim can be prepared for example as described in international application publication Nos. WO2013 / 025795 and WO2021 / 059160.

[0108] In some embodiments, the mixture is a tank mix.

[0109] The components of the mixture of the present invention can be applied either separately or as part of a multipart system.

[0110] The mixture of the present invention can be applied in conjunction with one or more other fungicides. When used in conjunction with other fungicide(s), the presently claimed compounds may be formulated with the other fungicide(s), tank mixed with the other fungicide(s) or applied sequentially with the other fungicide(s). Such other fungicides may include, but is not limited to, 2-(thiocyanatomethylthio)-benzothiazole, 2-phenylphenol, 8- hydroxyquinoline sulfate, ametoctradin, amisulbrom, antimycin, Ampelomyces quisqualis, azaconazole, azoxystrobin, Bacillus subtilis, Bacillus subtilis strain QST713, benalaxyl, benomyl, benthiavalicarb-isopropyl, benzylaminobenzene-sulfonate (BABS) salt, bicarbonates, biphenyl, bismerthiazol, bitertanol, bixafen, blasticidin-S, borax, Bordeaux mixture, boscalid, bromuconazole, bupirimate, calcium polysulfide, captafol, captan,carbendazim, carboxin, carpropamid, carvone, chlazafenone, chloroneb, chlorothalonil, chlozolinate, Coniothyrium minitans, copper hydroxide, copper octanoate, copper oxychloride, copper sulfate, copper sulfate (tribasic), cuprous oxide, cyazofamid, cyflufenamid, cymoxanil, cyproconazole, cyprodinil, dazomet, debacarb, diammonium ethylenebis-(dithiocarbamate), dichlofluanid, dichlorophen, diclocymet, diclomezine, dichloran, diethofencarb, difenoconazole, difenzoquat ion, diflumetorim, dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dinobuton, dinocap, diphenylamine, dithianon, dodemorph, dodemorph acetate, dodine, dodine free base, edifenphos, enestrobin, enestroburin, epoxiconazole, ethaboxam, ethoxyquin, etridiazole, famoxadone, fenamidone, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenoxanil, fenpiclonil, fenpropidin, fenpropimorph, fenpyrazamine, fentin, fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, flumorph, fluopicolide, fluopyram, fluoroimide, fluoxastrobin, fluquinconazole, flusilazole, flusulfamide, flutianil, flutolanil, flutriafol, fluxapyroxad, folpet, formaldehyde, fosetyl, fosetyl-aluminium, fuberidazole, furalaxyl, furametpyr, guazatine, guazatine acetates, GY-81, hexachlorobenzene, hexaconazole, hymexazol, imazalil, imazalil sulfate, imibenconazole, iminoctadine, iminoctadine triacetate, iminoctadine tris(albesilate), iodocarb, ipconazole, ipfenpyrazolone, iprobenfos, iprodione, iprovalicarb, isoprothiolane, isopyrazam, isotianil, kasugamycin, kasugamycin hydrochloride hydrate, kresoxim-methyl, laminarin, mancopper, mancozeb, mandipropamid, maneb, mefenoxam, mepanipyrim, mepronil, meptyl-dinocap, mercuric chloride, mercuric oxide, mercurous chloride, metalaxyl, metalaxyl-M, metam, metam- ammonium, metam-potassium, metam-sodium, metconazole, methasulfocarb, methyl iodide, methyl isothiocyanate, metiram, metominostrobin, metrafenone, mildiomycin, myclobutanil, nabam, nitrothal-isopropyl, nuarimol, octhilinone, ofurace, oleic acid (fatty acids), orysastrobin, oxadixyl, oxine-copper, oxpoconazole fumarate, oxycarboxin, pefurazoate, penconazole, pencycuron, penflufen, pentachlorophenol, pentachlorophenyl laurate, penthiopyrad, phenylmercury acetate, phosphonic acid, phthalide, picoxystrobin, polyoxin B, polyoxins, polyoxorim, potassium bicarbonate, potassium hydroxyquinoline sulfate, probenazole, prochloraz, procymidone, propamocarb, propamocarb hydrochloride, propiconazole, propineb, proquinazid, prothioconazole, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyrazophos, pyribencarb, pyributicarb, pyrifenox, pyrimethanil, pyriofenone, pyroquilon, quinoclamine, quinoxyfen, quintozene, Reynoutria sachalinensis extract, sedaxane, silthiofam, simeconazole, sodium 2- phenylphenoxide, sodium bicarbonate, sodium pentachlorophenoxide, spiroxamine, sulfur, SYP-Z048, tar oils, tebuconazole, tebufloquin, tecnazene, tetraconazole, thiabendazole, thifluzamide, thiophanate-methyl, thiram, tiadinil, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triazoxide, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole, validamycin, valifenalate, valiphenal, vinclozolin, zineb, ziram, zoxamide, Candida oleophila, Fusarium oxysporum, Gliocladium spp., Phlebiopsis gigantea, Streptomyces griseoviridis, Trichoderma spp., (RS)-N-(3,5-dichlorophenyl)-2- (methoxymethyl)-succinimide, 1,2-dichloropropane, l,3-dichloro-l,l,3,3-tetrafluoroacetone hydrate, l-chloro-2,4-dinitronaphthalene, 1 -chloro-2-nitropropane, 2-(2-heptadecyl-2- imidazolin- 1 -yl)ethanol, 2,3-dihydro-5-phenyl-l,4-dithi-ine 1,1,4,4-tetraoxide, 2- methoxyethylmercury acetate, 2-methoxyethylmercury chloride, 2-methoxyethylmercury silicate, 3-(4-chlorophenyl)-5-methylrhodanine, 4-(2-nitroprop-l-enyl)phenyl thiocyanateme, ampropylfos, anilazine, azithiram, barium polysulfide, Bayer 32394, benodanil, benquinox, bentaluron, benzamacril; benzamacril-isobutyl, benzamorf, binapacryl, bis(methylmercury)sulfate, bis(tributyltin) oxide, buthiobate, cadmium calcium copper zinc chromate sulfate, carbamorph, CECA, chlobenthiazone, chloraniformethan, chlorfenazole, chlorquinox, climbazole, copper bis(3-phenylsalicylate), copper zinc chromate, cufraneb, cupric hydrazinium sulfate, cuprobam, cyclafuramid, cypendazole, cyprofuram, decafentin, dichlone, dichlozoline, diclobutrazol, dimethirimol, dinocton, dinosulfon, dinoterbon, dipyrithione, ditalimfos, dodicin, drazoxolon, EBP, ESBP, etaconazole, etem, ethirim, fenaminosulf, fenapanil, fenitropan, fluotrimazole, furcarbanil, furconazole, furconazole-cis, furmecyclox, furophanate, glyodine, griseofulvin, halacrinate, Hercules 3944, hexylthiofos, ICIA0858, isopamphos, isovaledione, mebenil, mecarbinzid, metazoxolon, methfuroxam, methylmercury dicyandiamide, metsulfovax, milneb, mucochloric anhydride, myclozolin, N- 3,5-dichlorophenyl-succinimide, N-3-nitrophenylitaconimide, natamycin, N-ethylmercurio-4- toluenesulfonanilide, nickel bis(dimethyldithiocarbamate), OCH, phenylmercury dimethyldithiocarbamate, phenylmercury nitrate, phosdiphen, prothiocarb; prothiocarb hydrochloride, pyracarbolid, pyridinitril, pyroxychlor, pyroxyfur, quinacetol; quinacetol sulfate, quinazamid, quinconazole, rabenzazole, salicylanilide, SSF-109, sultropen, tecoram, thiadifluor, thicyofen, thiochlorfenphim, thiophanate, thioquinox, tioxymid, triamiphos, triarimol, triazbutil, trichlamide, urbacid, zarilamid, and any combinations thereof.

[0111] In some embodiments, the present invention provides a mixture comprising solid form of flumetylsulforim, compound I and an agricultural compound.

[0112] The present invention provides a composition comprising (a) one or more solids form of flumetylsulforim, and (b) a compound of Formula I selected from a group consisting of (1) 4-(Hydroxymethyl)benzene-l-sulfinic acid, (2) 5-fluoro-l-((4-(hydroxymethyl)phenyl)sulfonyl)-4-imino-3-methyl-3,4-dihydropyrimidin-2(lH)-one, (3) 2,4- Pyrimidinedione, 5-fluoro-3-methyl-l-[(4-methylphenyl)sulfonyl], (4) (E)-2-fluoro-3-lmino-3- (methylamino)-l-(p-tolylsulfonylamino)l-propene and (5) [p-(3-Methylureidosulfonyl)phenyl] methanol.

[0113] In some embodiments, the composition further comprises a surfactant.

[0114] Concentrated formulations can be dispersed in water, or another liquid for application, or formulations can be dust-like or granular, which can then be applied without further treatment.

[0115] The formulations that are applied most often are aqueous suspensions or emulsions. Either such water-soluble, water suspendable, or emulsifiable formulations are either solids such as wettable powders, or liquids, such as emulsifiable concentrates, aqueous suspensions, or suspension concentrates. The present invention contemplates all vehicles by which the compositions can be formulated for delivery and use as, for example, a fungicide.

[0116] As will be readily appreciated, any material to which these compositions can be added may be used, provided they yield the desired utility without significant interference with the activity of these compositions.

[0117] In some embodiments, the composition further comprises at least one agriculturally acceptable inert additive, such as sticking agents, surfactants, synergists, buffers, acidifiers, anti-oxidation agent, defoaming agents and thickeners.

[0118] In some embodiments, the composition comprises Flumetylsulforim and agricultural acceptable carrier such as water and / or organic solvent.

[0119] The formulations may contain agriculturally acceptable adjuvant. These adjuvant surfactants may optionally be employed as a component of the formulation or as a tank mix.

[0120] The present invention includes within its scope methods for treating a plant or locus against fungal infection. The present invention further includes within its scope methods for the control or prevention of fungal attack. These methods comprise applying to the locus of the fungus, or to a locus in which the infestation is to be prevented (for example applying to wheat or barley plants), the mixture or composition described in the present invention. The composition is suitable for treatment of various plants, while exhibiting non or low phytotoxicity. The composition is useful in a protectant or eradicant fashion. The composition is applied by any of a variety of known techniques, either as the composition or as a formulation comprising the composition. For example, the compositions may be applied to the roots, seeds or foliage of plants for the control of various fungi, without damaging the plants. The composition is applied in the form of any of the generally used formulation types, for example, as solutions, dusts, wettable powders, flowable concentrates, or emulsifiable concentrates. These materials are conveniently applied in various known fashions.

[0121] The mixture and composition described herein have been found to have significant fungicidal effect particularly for agricultural use. The composition is particularly effective for use with agricultural crops and horticultural plants.

[0122] In particular, the composition is effective in controlling a variety of undesirable fungi that infect useful plant crops. The mixtures and compositions described herein may be applied to control and / or prevent a variety of fungal pathogen and diseases associated therewith. In some embodiments, the fungal pathogen is one of Mycosphaerella graminicola, Septoria tritici, Puccinia triticina, Puccinia striiformis f. sp. tritici, Venturia inaequalis, Ustilago maydis, Uncinula necator, Rhynchosporium secalis, Magnaporthe grisea, Phakopsora pachyrhizi, Leptosphaeria nodorum, Blumeria graminis f. sp. tritici, Blumeria graminis f. sp. hordei, Erysiphe cichoracearum, Glomerella lagenarium, Cercospora beticola, Alternaria solani, Pyrenophora teres, Ramularia, Peronospora spp., Botrytis cinereal, and Mycosphaerella fijiensis.

[0123] In some embodiments, the fungal pathogen is Septoria. In some embodiments, the fungal pathogen is Zymoseptoria tritici (SEPTTR). In some embodiments, the fungal pathogen is Rhyncosporium. In some embodiments, the fungal pathogen is Pyrenophora. In some embodiments, the fungal pathogen is Microduchium majus. In some embodiments, the fungal pathogen is Sclerotinia. In some embodiments, the fungal pathogen is Cercosporea beticola.

[0124] In some embodiments, the fungal disease is one of Leaf Blotch of Wheat (Mycosphaerella graminicola; anamorph: Septoria tritici), Wheat Brown Rust (Pucciniatriticina), Stripe Rust (Puccinia striiformis f. sp. tritici), Scab of Apple (Venturia inaequalis), Blister Smut of Maize (Ustilago maydis), Powdery Mildew of Grapevine (Uncinula necator), Barley scald (Rhynchosporium secalis), Blast of Rice (Magnaporthe grisea), Rust of Soybean (Phakopsora pachyrhizi), Glume Blotch of Wheat (Leptosphaeria nodorum), Powdery Mildew of Wheat (Blumeria graminis f. sp. tritici), Powdery Mildew of Barley (Blumeria graminis f. sp. hordei), Powdery Mildew of Cucurbits (Erysiphe cichoracearum), Anthracnose of Cucurbits (Glomerella lagenarium), Leaf Spot of Beet (Cercospora beticola), Early Blight of Tomato (Alternaria solani), Net Blotch of Barley (Pyrenophora teres), Downy Mildew of vegetables (Peronospora spp.), Downy Mildew of Brassicas (Peronospora spp.), Downy Mildew of Cucurbits (Peronospora spp.), Gray Mold of Grape (Botrytis cinereal), Gray Mold of Vegetables (Botrytis cinereal), and Banana Black sigatoka (Mycosphaerella fijiensis).

[0125] In some embodiments, the plant or soil disease is one of leaf spot, brown rust, yellow rust, powdery mildew, downy mildew, gray mold, Asian soybean rust, and black sigatoka.

[0126] In some embodiments, the plant is a crop plant. The methods of the present invention may be used on any crop plants, including but not limited to monocotyledons such as sugar cane cereals, rice, maize (corn), and / or; or dicotyledon crop such as beets (such as sugar beet or fodder beet); fruits (such as pomes, stone fruits, or soft fruits, for example apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, or blackberries); leguminous plants (such as beans, lentils, peas, or soybeans); oil plants (such as rape, mustard, poppy, olives, sunflowers, coconut, castor oil plants, cocoa beans, or groundnuts); cucumber plants (such as marrows, cucumbers or melons); fiber plants (such as cotton, flax, hemp, or jute); citrus fruits (such as oranges, lemons, grapefruit, or mandarins); vegetables (such as spinach, lettuce, cabbages, carrots, tomatoes, potatoes, cucurbits, or paprika); lauraceae (such as avocados, cinnamon, or camphor); tobacco; nuts; coffee; tea; vines; hops; durian; bananas; natural rubber plants; and ornamentals (such as flowers, shrubs, broad-leaved trees, or evergreens, for example conifers).

[0127] In some embodiments, the plants are monocotyledonous plants, more preferably, cereals. In a specific embodiment, the cereal crop is wheat. In another specific embodiment, the cereal crop is triticale. In another specific embodiment, the cereal crop is rye. In another specific embodiment, the cereal crop is oat. In a further embodiment, the cereal crop is barley. In another embodiment, the crop plants are rice plants. In still another embodiment, the crop plants are sugar cane plants. In yet another embodiment, the crop plants are corn plants.

[0128] In another embodiment, the crop plants are dicotyledonous plants.

[0129] In some embodiments, the crop plants are oil seed rape plants. The mixtures and compositions have a broad range of efficacy as a fungicide. The exact amount of the composition or mixture to be applied is dependent not only on the relative amounts of the components, but also on the particular action desired, the fungal species to be controlled, and the stage of growth thereof, as well as the part of the plant or other product to be contacted with the composition.

[0130] The present invention further includes within its scope the use of the mixture or composition described herein for treating a plant or locus against fungal infection. The presentmixtures or compositions can be applied to fungi or their locus by the use of conventional ground sprayers, granule applicators, and by other conventional means known to those skilled in the art.

[0131] The rate at which the composition is applied will depend upon the particular type of fungus to be controlled, the degree of control required and the timing and method of application. In general, the composition of the invention can be applied at an application rate of between about 50 grams per hectare (g / ha) and about 3000 g / ha based on the total amount of active ingredients in the composition.

[0132] The present invention provides use of at least one Compound I described herein as reference standard (1) for determining purity and / or metabolite profile of solid form of Flumetylsulforim, (2) for determining purity of a composition comprising solid form of Flumetylsulforim, (3) to test for its presence and / or quantity in solid form of Flumetylsulforim, (4) to test for its presence and / or quantity in a composition, (5) to test for its presence and / or quantity at a locus where solid form of Flumetylsulforim was applied and / or (6) to test for its presence and / or quantity in a plant to which solid form of Flumetylsulforim was applied.

[0133] The subject invention is further directed to use of Compound I as reference standard for determining purity and / or metabolite profile of solid form of Flumetylsulforim.

[0134] In some embodiments, the Compound I has the structure A as describe herein.

[0135] In some embodiments, the Compound I having the structure A is used as reference standard for determining purity and / or metabolite profile of solid form of Flumetylsulforim as described herein.

[0136] In some embodiments, the Compound I has the structure B as describe herein.

[0137] In some embodiments, the Compound I having the structure B is used as reference standard for determining purity and / or metabolite profile of solid form of Flumetylsulforim as described herein.

[0138] In some embodiments, the Compound I has the structure C as describe herein.

[0139] In some embodiments, the Compound I having the structure C is used as reference standard for determining purity and / or metabolite profile of solid form of Flumetylsulforim as described herein.

[0140] In some embodiments, the Compound I has the structure D as describe herein.

[0141] In some embodiments, the Compound I having the structure D is used as reference standard for determining purity and / or metabolite profile of solid form of Flumetylsulforim as described herein.

[0142] In some embodiments, the Compound I has the structure E as describe herein.

[0143] In some embodiments, the Compound I having the structure E is used as reference standard for determining purity and / or metabolite profile of solid form of Flumetylsulforim as described herein.

[0144] The present invention provides use of the Compound I as reference standard for determining the purity of a composition comprising solid form of Flumetylsulforim.

[0145] In some embodiments, the Compound I has the structure A as describe herein.

[0146] In some embodiments, compound I having the structure A is used as reference standard for determining the purity of a composition comprising a solid form of Flumetylsulforim.

[0147] In some embodiments, the Compound I has the structure B as describe herein.

[0148] In some embodiments, compound I having the structure B is used as reference standard for determining the purity of a composition comprising a solid form of Flumetylsulforim.

[0149] In some embodiments, the Compound I has the structure C as describe herein.

[0150] In some embodiments, compound I having the structure C is used as reference standard for determining the purity of a composition comprising a solid form of Flumetylsulforim.

[0151] In some embodiments, the Compound I has the structure D as describe herein.

[0152] In some embodiments, compound I having the structure D is used as reference standard for determining the purity of a composition comprising a solid form of Flumetylsulforim.

[0153] In some embodiments, the Compound I has the structure E as describe herein.

[0154] In some embodiments, compound I having the structure E is used as reference standard for determining the purity of a composition comprising a solid form of Flumetylsulforim.

[0155] The present invention provides use of Compound I as a reference standard to test for the presence and / or quantity of the compound I in solid form of Flumetylsulforim.

[0156] In some embodiments, compound I has the structure A as describe herein.

[0157] In some embodiments, compound I having the structure A is used as reference standard to test for the presence and / or quantity of the compound I in solid form of Flumetylsulforim.

[0158] In some embodiments, compound I has the structure B as describe herein.

[0159] In some embodiments, compound I having the structure B is used as reference standard to test for the presence and / or quantity of the compound I in solid form of Flumetylsulforim.

[0160] In some embodiments, compound I has the structure C as describe herein.

[0161] In some embodiments, compound I having the structure C is used as reference standard to test for the presence and / or quantity of the compound I in solid form of Flumetylsulforim.

[0162] In some embodiments, compound I has the structure D as describe herein.

[0163] In some embodiments, compound I having the structure D is used as reference standard to test for the presence and / or quantity of the compound I in solid form of Flumetylsulforim.

[0164] In some embodiments, compound I has the structure E as describe herein.

[0165] In some embodiments, compound I having the structure E is used as reference standard to test for the presence and / or quantity of the compound I in solid form of Flumetylsulforim.

[0166] The present invention provides use of Compound I as a reference standard to test for the presence and / or quantity of the compound I in a composition.

[0167] In some embodiments, the compound I has the structure A as describe herein.

[0168] In some embodiments, the compound I having the structure A is used as reference standard to test for the presence and / or quantity of the compound I in a composition.

[0169] In some embodiments, the compound I has the structure B as describe herein.

[0170] In some embodiments, the compound I having the structure B is used as reference standard to test for the presence and / or quantity of the compound I in a composition.

[0171] In some embodiments, the compound I has the structure C as describe herein.

[0172] In some embodiments, the compound I having the structure C is used as reference standard to test for the presence and / or quantity of the compound I in a composition.

[0173] In some embodiments, the compound I has the structure D as describe herein.

[0174] In some embodiments, the compound I having the structure D is used as reference standard to test for the presence and / or quantity of the compound I in a composition.

[0175] In some embodiments, the compound I has the structure E as describe herein.

[0176] In some embodiments, the compound I having the structure E is used as reference standard to test for the presence and / or quantity of the compound I in a composition.

[0177] In some embodiments, the composition is a composition comprising Flumetylsulforim mixture as described herein.

[0178] The present invention provides use of Compound I as reference standard to test for the presence and / or quantity of the compound I at a locus where solid form of Flumetylsulforim was applied.

[0179] In some embodiments, the compound I has the structure A as describe herein.

[0180] In some embodiments, compound I having the structure A as described herein is used as reference standard to test for the presence and / or quantity of the compound I at a locus where solid form of Flumetylsulforim was applied.

[0181] In some embodiments, the compound I has the structure B as describe herein.

[0182] In some embodiments, compound I having the structure B as described herein is used as reference standard to test for the presence and / or quantity of the compound I at a locus where solid form of Flumetylsulforim was applied.

[0183] In some embodiments, the compound I has the structure C as describe herein.

[0184] In some embodiments, compound I having the structure C as described herein is used as reference standard to test for the presence and / or quantity of the compound I at a locus where solid form of Flumetylsulforim was applied.

[0185] In some embodiments, the compound I has the structure D as describe herein.

[0186] In some embodiments, compound I having the structure D as described herein is used as reference standard to test for the presence and / or quantity of the compound I at a locus where solid form of Flumetylsulforim was applied.

[0187] In some embodiments, the compound I has the structure E as describe herein.

[0188] In some embodiments, compound I having the structure E as described herein is used as reference standard to test for the presence and / or quantity of the compound I at a locus where solid form of Flumetylsulforim was applied.

[0189] The present invention provides use of Compound I as reference standard to test for the presence and / or quantity of the compound I in a plant to which solid form of Flumetylsulforim was applied.

[0190] In some embodiments, the compound I has the structure A as describe herein.

[0191] In some embodiments, the compound I having the structure A is used as reference standard to test for the presence and / or quantity of the compound I in a plant to which solid form of Flumetylsulforim was applied.

[0192] In some embodiments, the compound I has the structure B as describe herein.

[0193] In some embodiments, the compound I having the structure B is used as reference standard to test for the presence and / or quantity of the compound I in a plant to which solid form of Flumetylsulforim was applied.

[0194] In some embodiments, the compound I has the structure C as describe herein.

[0195] In some embodiments, the compound I having the structure C is used as reference standard to test for the presence and / or quantity of the compound I in a plant to which solid form of Flumetylsulforim was applied.

[0196] In some embodiments, the compound I has the structure D as describe herein.

[0197] In some embodiments, the compound I having the structure D is used as reference standard to test for the presence and / or quantity of the compound I in a plant to which solid form of Flumetylsulforim was applied.

[0198] In some embodiments, the compound I has the structure E as describe herein.

[0199] In some embodiments, the compound I having the structure E is used as reference standard to test for the presence and / or quantity of the compound I in a plant to which solid form of Flumetylsulforim was applied.

Claims

Claims1. A mixture comprising (a) one or more solid forms of flumetylsulforim, and (b) one or more Compound I selected from a group consisting of (1) 4-(Hydroxymethyl)benzene-l- sulfinic acid, (2) 5-fluoro-l-((4-(hydroxymethyl)phenyl)sulfonyl)-4-imino-3-methyl-3,4- dihydropyrimidin-2(lH)-one, (3) 2,4-Pyrimidinedione, 5-fluoro-3-methyl-l-[(4- methylphenyl)sulfonyl], (4) (E)-2-fluoro-3-lmino-3-(methylamino)-l-(p-tolylsulfonylamino)l- propene and (5) [p-(3-Methylureidosulfonyl)phenyl]methanol.

2. The mixture of claim 1, wherein the solid form of flumetylsulforim is amorphous, crystalline, solvate or hydrate.

3. A composition comprising the mixture of claim 1 or 2.

4. Use of the mixture or composition of any one of claims 1-3 for treating a plant or locus against fungal infection.

5. Use of the mixture or composition of any one of claims 1-3 for controlling or preventing a fungal attack.

6. The mixture or composition of any one of claims 1-3 for use to treat a plant or locus against fungal infection.

7. Use of the Compound I as reference standard for determining purity and / or metabolite profile of a mixture comprising solid form of Flumetylsulforim.

8. Use of the Compound I as reference standard for determining the purity of a composition comprising a solid form of Flumetylsulforim.

9. Use of Compound I as a reference standard to test for the presence and / or quantity of the compound I in solid form of Flumetylsulforim.

10. Use Compound I as a reference standard to test for the presence and / or quantity of the compound I in a composition.

11. Use of Compound I as reference standard to test for the presence and / or quantity of the compound I at a locus where solid form of Flumetylsulforim was applied.

12. Use of Compound I as reference standard to test for the presence and / or quantity of the compound I in a plant to which solid form of Flumetylsulforim was applied.

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