Mixtures and composition comprising thereof

Abstract

The present invention relates to mixtures comprising: (a) agricultural material, especially a fungicide and (b) one or more 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), 5-fluoro-3-methyl-l- [(4-methylphenyl)sulfonyl]-2,4-pyrimidinedione; (4) (E)-2-fluoro-3- lmino-3-(methylamino)-l-(p-tolylsulfonylamino)l-propene; and (5) [p- (3-methylureidosulfonyl)phenyl]methanol. The invention also relates to the use of the mixtures or compositions comprising these mixtures as antifungal agents or reference standards.

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. herein after often referred to for textural convenience only, as "Compound I Mix(es)" comprising: (a) agricultural material, and (b) one or more of a group of compounds hereinafter referred to collectively as Compound I, and compositions comprising one or more of these "Compound I Mix(es)", wherein compound I is selected from: (1) 4-(Hydroxymethyl)benzene-l-sulfinic acid, (2) 5- fluoro-l-((4-(hydroxymethyl)phenyl)suifonyl)-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 .Background of the Invention

[0002] Patent application PCT / US2006 / 017994 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.

[0003] It is well known that even when an analytical method is capable of resolving the signals, peaks etc., of a compound and its degradant, metabolite, impurity etc., by chromatographic methods e.g., by HPLC, it is often difficult to accurately establish the exact percentage content of such an impurity / metabolite by a simple comparison of peak height or area as of the resultant chromatogram, as differences in the chemical characteristics often means that there is a difference in the detector signal sensitivity for each, sometimes this is a difference in extinction coefficient. The aforementioned difficulties are further compounded when the sample being analyzed comprises two or more chemical compounds each with its own different HPLC system suitable for only one of the analytes, especially when a suspected impurity in the combination that is the subject of the analysis is not well known and scant information as regards analytical methodology is available.

[0004] As such, in the above example even if an associated with the suspected impurity peak is resolved in one or both of the analytical methods, it can be near impossible to accurately reach a determination as to an accurate percentage content in the original sample, especially when a degradant, impurity, metabolite of one compound in a mixture is only resolved in the chromatographic methodology relevant to the other component. Thus, the only way to be able to conduct such an analysis on a such a mixture quickly and accurately is to prepare calibration combinations with which analytical results of a sample are compared. However, this is not possible when the suspected compound is a novel compound never before associated with that mixture.

[0005] Inventors provide identification of "Compound I" as being associated with Flumetylsulforim.

[0006] Further, inventors provide multi-component, Compound I Mix(es) comprising, specific useful combinations comprising those identified Compound I compounds with other agriculturally relevant compounds. These newly revealed Compound I Mixes are useful inter alia in establishing combination-specific chemical analysis of samples containing mixtures of Flumetylsulforim with agrochemically relevant compounds such as further pesticidal compounds or formulation component compounds of pesticidal Flumetylsulforim formulations such as co-formulants, adjuvants etc.

[0007] While the joint shared utility of the whole range of Compound I Mixes has been clearly defined above it is surprisingly found that several individual multi-component combinations herein disclosed have uses beyond the shared utility of being analytical calibration standards due to the surprising interaction between those Flumetylsulforim degradant, impurity or metabolite compounds and the specific other agriculturally relevant component of that mixture.Summary of the Invention

[0008] The present invention provides Compound I Mix(es) comprising: (a) one or more agricultural material, 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.

[0009] The present invention provides compositions comprising: (a) one or more agricultural material, 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.

[0010] The present invention provides use of Compound I Mix(es) as reference standard for determining purity and / or metabolite profile of a mixture comprising Flumetylsulforim.

[0011] The present invention provides use of Compound I Mix(es) as reference standard for determining the purity of a composition comprising a Flumetylsulforim mixture.

[0012] The present invention provides use of Compound I Mix(es) as a reference standard to test for its presence and / or quantity in a Flumetylsulforim mixture.

[0013] The present invention provides use of Compound I Mix(es) as a reference standard to test for its presence and / or quantity in a composition.

[0014] The present invention provides a method for monitoring the stability of a composition comprising Flumetylsulforim mixture, the method comprising measuring the concentration of Compound I Mix(es) in the composition, wherein increase in the concentration of the Compound I Mix(es), indicates degradation of Flumetylsulforim mixture.[□015] in some embodiments, the composition is a composition comprising Flumetylsulforim mixture as described herein.

[0016] The present invention provides use of Compound i Mix(es) as reference standard to test for its presence and / or quantity at a locus where Flumetylsulforim mixture was applied.

[0017] The present invention provides use of Compound I Mix(es) as reference standard to test for its presence and / or quantity in a plant to which Flumetylsulforim mixture was applied.Brief Description of The DrawingsFigure 1: 1H NMR spectrum of structure A.Figure 2: 1H NMR (CDCI3, 300MHz) of structure B.Figure 3: Mass spectrum of structure C.Figure 4: 1H NMR spectrum of structure D.Figure 5: 1H NMR spectrum of structure E.Detailed Description of the InventionDefinitions

[0018] 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.

[0019] 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."

[0020] 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.

[0021] 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.[□022] 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.

[0023] 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.

[0024] 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.).

[0025] As used herein, the terms "composition" and "formulation" are interchangeable.

[0026] As used herein, the term "agricultural material" means an ingredient used in the practice of farming, including cultivation of the soil for the growing of crops. However, the use of agricultural materials is not limited to application to crops. Agricultural materials may be applied to any surface, e.g., for the purpose of cleaning or aiding or inhibiting growth of a living organism. Other non-crop applications include, but are not limited to, application to an animal, e.g. livestock, application to turf and ornamentals, and application to railroad weed.

[0027] As used herein, the term "agrochemical" is a chemical active ingredient used in the practice of farming, including cultivation of the soil for the growing of crops. However, the use of agrochemicals is not limited to application to crops. Agrochemicals may be applied to any surface, e.g., for the purpose of cleaning or aiding or inhibiting growth of a living organism.

[0028] Examples of agricultural materials include agrochemicals.

[0029] Examples of agricultural materials and agrochemicals include, but are not limited to, pesticides, hormones, bio-stimulants, and plant growth agents.

[0030] As used herein, the term "pesticide", "pesticide compound" or "pesticidal compound" means a compound capable of killing or inhibiting growth or proliferation of a pest, whether for plant protection or for non-crop application. As used herein, all "pesticide", "pesticide compound" or "pesticidal compound" fall within "agricultural material compound". The term "pesticide", "pesticide compound" or "pesticidal compound" includes, but is not limited to, insecticide, nematicide, herbicide, fungicide, algicides, animal repellents, and acaricides. As used herein, the term "pest" includes, but is not limited to, insect, nematode, weed, fungi, algae, mite, tick, and animal. As used herein, the term "weed" refers to any unwanted vegetation.

[0031] 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) [p-(3-Methylureidosulfonyl)phenyl]methanol.

[0032] Flumetylsulforim includes all solid forms thereof including, but not limited to, amorphous, crystalline, solvate or hydrate. Crystalline forms of Flumetylsulforim are disclosed in PCT International Application Publication No. WO 2019 / 038583 Al, published February 28, 2019, and WO 2022 / 234487, published November 10, 2022, the entire content of which is hereby incorporated by reference.

[0033] 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. There is a need for standards for mixtures.

[0034] The present invention concerns mixture comprising (a) at least one agricultural material 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, S-fluoro-3- methyl-l-[(4-methylphenyl)sulfonyl], (4) (E)-2-fluoro-3-lmino-3-(methylamino)-l-(p- tolylsulfonylaminojl-propene and (5) [p-(3-Methylureidosulfonyl)phenyl]methanol.

[0035] In some embodiments, the agricultural material is an agrochemical.

[0036] In some embodiments, the agricultural material is a plant growth regulator. In some embodiment, the agricultural material is a bio-stimulant. In some embodiments, the agricultural material is a hormone.

[0037] In some embodiments, the agricultural material is agriculturally acceptable additive, such an adjuvant or surfactant, as described herein.

[0038] In some embodiments, the adjuvant is as described in international application publication no. WO2021224802.

[0039] In some embodiments, the agricultural material is a pesticide.

[0040] In some embodiments, the pesticide is an insecticide. In some embodiments, the pesticide is a nematicide. In some embodiments, the pesticide is an herbicide. In some embodiments, the pesticide compound is a fungicide. In some embodiments, the pesticide is an algicide. In some embodiments, the pesticide is an animal repellent. In some embodiments, the pesticide is an acaricide.

[0041] Examples of herbicides may include, but are not limited to, atrazine, diuron, chlorotoiuron, clethodim, clomazone, and tebuthiuron.

[0042] Examples of insecticides and acaricides may include, but are not limited to, abamectin, pyriproxyfen, acetamiprid, bifenthrin, cyfluthrin, pymetrozine, novaluron, ethiprole, fipronil, and lambda-cyhalothrin.

[0043] In some embodiments, the fungicide is selected from a group consisting of multi-site contact fungicide, Qil fungicide (quinone inside inhibitors), Qol fungicide (quinone outside inhibitors) QoSI fungicide (quinone outside stigmatellin subsite inhibitors), SDH! fungicide(succinate dehydrogenase inhibitors), Demethyiation Inhibitor fungicide, phenyl amide fungicide, methyl-benzimidazole-carbamate (MBC) fungicide, carboxylic acid amide fungicide, benzamide fungicide, natural fungicide, anilinopyrimidine fungicide, hydroxy-(2-amino)- pyrimidines fungicide, phosphonate fungicide, plant extract fungicide, Keto-Reductase inhibitor fungicide, phenylpyrrole fungicide (PP), aryl phenyl-ketone fungicide, amine fungicide, dinitro aniline fungicide, azanaphthalene fungicide, benzothiadiazole fungicide, carbamate fungicide, cyanoacetamideoxime fungicide, dinitrophenyl-crotonate fungicide, glucopyranosyl antibiotic fungicide, tetrazoiyloxime fungicide, thiazolidine fungicide, oxysterol binding protein inhibitor (OSBPI) fungicide, thiophenecarboxamide fungicide, phenylacetamide fungicide, phenyl urea fungicide, polyene fungicide, pyr-hydrazone fungicide, pyrimidinamine fungicide, pyrimidinone fungicide, fungicide (B), heteroaromatics, aromatic hydrocarbons (AH fungicides), quinoxyfen; benzenesulfonamides, probenazole, tridemorph, iprovalicarb, dicarboximides, dithiolanes, growth regulators, guanidine, fluoxythioconazole, ipfentrifluconazole, triadimefon, trifiumizole, hexopyranosyi antibiotics, bordeaux-mixture; benomyl, Melanin Biosynthesis Inhibitors - Reductase (MBI-R), microbials, n-phenyl carbamates, organo tin compounds, oxadixyl, potassium-bicarbonate, potassiumcarbonate, polyoxins, fenamidone, metarylpicoxamid, tetracycline antibiotics, uncouplers of oxidative phosphorylation, chlorinconazide, flufenoxadiazam, ipflufenoquin, pyridachlometyl, propamocarb-HCI, propiconazole and / or benthiavaiicarb-isopropyl.

[0044] In some embodiments, the fungicide is multi-site contact fungicide, in some embodiments, the fungicide is Qil fungicide (quinone inside inhibitors). In some embodiments, the fungicide is Qol fungicide (quinone outside inhibitors). In some embodiments, the fungicide is QoSI fungicide (quinone outside stigmatellin subsite inhibitors). In some embodiments, the fungicide is SDHI fungicide (succinate dehydrogenase inhibitors). In some embodiments, the fungicide is a demethyiation inhibitor fungicide (DMI fungicide). In some embodiments, the fungicide is phenyl amide fungicide. In some embodiments, the fungicide is methyl-benzimidazole-carbamate (MBC) fungicide. In some embodiments, the fungicide is carboxylic acid amide fungicide. In some embodiments, the fungicide is benzamide fungicide. In some embodiments, the fungicide is natural fungicide. In some embodiments, the fungicide is anilinopyrimidine fungicide. In some embodiments, the fungicide is hydroxy-(2-amino)- pyrimidines fungicide. In some embodiments, the fungicide is phosphonate fungicide. In some embodiments, the fungicide is plant extract fungicide. In some embodiments, the fungicide is Keto-Reductase inhibitor fungicide. In some embodiments, the fungicide is phenylpyrrole fungicide (PP). In some embodiments, the fungicide is aryl phenyl-ketone fungicide. In some embodiments, the fungicide in amine fungicide. In some embodiments, the fungicide is dinitro aniline fungicide. In some embodiments, the fungicide is azanaphthalene fungicide. In some embodiments, the fungicide is benzothiadiazole fungicide. In some embodiments, the fungicide is carbamate fungicide. In some embodiments, the fungicide is cyanoacetamideoxime fungicide. In some embodiments, the fungicide is dinitrophenyl- crotonate fungicide. In some embodiments, the fungicide is glucopyranosyl antibiotic fungicide. In some embodiments, the fungicide is tetrazoiyloxime fungicide. In some embodiments, the fungicide is thiazolidine fungicide. In some embodiments, the fungicide is oxysterol binding protein inhibitor (OSBPI) fungicide. In some embodiments, the fungicide is thiophenecarboxamide fungicide. In some embodiments, the fungicide is phenylacetamide fungicide. In some embodiments, the fungicide is phenyl urea fungicide. In someembodiments, the fungicide is polyene fungicide. In some embodiments, the fungicide is pyr- hydrazone fungicide. In some embodiments, the fungicide is pyrimidinamine fungicide. In some embodiments, the fungicide is pyrimidinone fungicide. In some embodiments, the fungicide is fungicide (B). In some embodiments, the fungicide is heteroaromatic. In some embodiments, the fungicide is aromatic hydrocarbon (AH fungicides). In some embodiments, the fungicide is quinoxyfen. In some embodiments, the fungicide is benzenesulfonamides. In some embodiments, the fungicide is probenazole. In some embodiments, the fungicide is tridemorph. In some embodiments, the fungicide is iprovalicarb. In some embodiments, the fungicide is dicarboximide. In some embodiments, the fungicide is dithiolane. In some embodiments, the fungicide is growth regulator. In some embodiments, the fungicide is guanidine. In some embodiments, the fungicide is fluoxythioconazole. In some embodiments, the fungicide is ipfentrifluconazole. In some embodiments, the fungicide is triadimefon. In some embodiments, the fungicide is trifiumizole. In some embodiments, the fungicide is hexopyranosyl antibiotics. In some embodiments, the fungicide is bordeaux-mixture. In some embodiments, the fungicide is benomyl. In some embodiments, the fungicide is Melanin Biosynthesis Inhibitor - Reductase (MBI-R). In some embodiments, the fungicide is microbial. In some embodiments, the fungicide is n-phenyl carbamate. In some embodiments, the fungicide is organo tin compound. In some embodiments, the fungicide is oxadixyl. In some embodiments, the fungicide is potassium-bicarbonate. In some embodiments, the fungicide is potassium-carbonate. In some embodiments, the fungicide is polyoxin. In some embodiments, the fungicide is fenamidone. In some embodiments, the fungicide is metarylpicoxamid. In some embodiments, the fungicide is tetracycline antibiotic. In some embodiments, the fungicide is uncoupler of oxidative phosphorylation. In some embodiments, the fungicide is chlorinconazide. In some embodiments, the fungicide is flufenoxadiazam. In some embodiments, the fungicide is ipflufenoquin. In some embodiments, the fungicide is pyridachlometyl. In some embodiments, the fungicide is propamocarb-HCl. In some embodiments, the fungicide is propiconazole. In some embodiments, the fungicide is benthiavalicarb-isopropyl.

[0045] The multi-site contact fungicide according to the invention inhibits fungal growth through multiple sites of action. The term contact fungicide as used herein denotes a fungicide that remains at the site where it is applied but does not travel within the plant.

[0046] Multi-site contact fungicide according to the invention is selected from the group consisting of phthalimides, thiocarbamate, maleimide, quinoxalines, quinones, triazines, bisguanidines, sulfamides, chloronitriles, dithio-carbamates, inorganic fungicide and any combination thereof.

[0047] In some embodiment, the phthalimide fungicide is selected from the group consisting of captan, folpet, captafol, and any combination thereof. In some embodiments, the thiocarbamate is methasulfocarb. In some embodiments, maleimide is fluoroimide. In some embodiments, the quinoxaline is selected from the group consisting of chinomethionat, quinomethionate, and a combination thereof. In some embodiments, the quinone is dithianon. In some embodiments, the triazine is anilazine. In some embodiments, the bisguanidine is selected from the group consisting of guazatine, iminoctadine, iminoctadine- triacetate and any combination thereof. In some embodiments, the sulfamide is selected fromthe group consisting of dichlofluanid, tolylfluanid and any combination thereof. In some embodiments, the chloronitrile is chlorothalonil. In some embodiments, the dithio-carbamate is selected from the group consisting of ferbam, mancozeb, maneb, metiram, propineb, thiram, zinc thiazole, zineb, ziram and any combination thereof. In some embodiments, the inorganic fungicide is selected from the group consisting of copper, sulphur and a combination thereof.[0048} In some embodiments, the phthalimide fungicide is captan. In some embodiments, the phthalimide fungicide is folpet.[0049} In some embodiments, the multi-site contact fungicide is selected from the group consisting of copper, sulphur, anilazine, dithianon, febram, mancozeb, zinc thiazole, chlorothalonil, maneb, propineb, metiram, thiram, zineb, ziram and any combination thereof. In some embodiments, the multi-site contact fungicide is selected from the group consisting of copper, sulphur, and any combination thereof. In some embodiments, the multi-site contact fungicide is sulphur. In some embodiments, the multi-site contact fungicide is copper. In some embodiments, the multi-site contact fungicide is mancozeb. In some embodiments, the multi-site contact fungicide is chlorothalonil.

[0050] As used herein, the term "copper" includes all forms of copper, such as copper oxychloride, copper sulphate, copper hydroxide and its complexes or chelates with amino acids, peptides, EDTA, urea, and octanoic or gluconic acids.

[0051] In some embodiments, the Qil (quinone inside inhibitors) is selected from the group consisting of amisulbrom, cyazofamid, fenpicoxamid and any combination thereof.

[0052] In some embodiments, the Qil (quinone inside inhibitors) is amisulbrom. In some embodiments, the Q.II (quinone inside inhibitors) is cyazofamid. In some embodiments, the Qil (quinone inside inhibitors) is fenpicoxamid.

[0053] In some embodiments, the Qol (quinone outside inhibitors) is selected from the group consisting of azoxystrobin, kresoxim-methyl, picoxystrobin, fluxastrobin, dimoxystrobin, pyraclostrobin, trifloxystrobin, coumoxystrobin, fenaminstrobin, pyrametostrobin, triclopyricarb, pyribencarb, pyraoxystrobin, metyltetraprole, mandestrobin, famoxadone, oryzastrobin, enoxastrobin, pyraclostrobin, fluoxastrobin, flufenostrin, flufenoxystrobin, metominostrobin, triclopyricarb; pyriminostrobin, florylpicoxamid, and any combination thereof. Each alternative represents a separate embodiment.[0054} In some embodiments, the Qol (quinone outside inhibitors) is azoxystrobin. In some embodiments, the Qol (quinone outside inhibitors) is picoxystrobin.[0055} In some embodiments, the QoSI (quinone outside stigmatellin inhibitors) is ametoctradin.[0056} In some embodiments, the SDHI (succinate dehydrogenase inhibitors) fungicide is selected from the group consisting of fluxapyroxad, penflufen, bixafen, isopyrazam, sedaxane, benzovindiflupyr, thifluzamide, isofetamid, fluopyram, pydiflumetofen, pyraziflumid, fl utolanil, carboxin, boscalid, fluindapyr, penthiopyrad, isoflucypram inpyrfluxam, furametpyr,benodanil, mepronil, fenfuram, oxycarboxin, pyrapropoyne, flubeneteram, quinofumelin and any combination thereof. Each alternative represents a separate embodiment.

[0057] In some embodiments, the SDHI fungicide is fiuxapyroxad. In some embodiments, the SDHI fungicide is benzovindiflupyr. In some embodiments, the SDHI fungicide is penflufen.

[0058] In some embodiments, the demethylation inhibitor fungicide (DM! fungicide) is selected from the group consisting of ipconazole, tebuconazole, metconazole, fenbuconazole, bromuconazole, tetraconazole, flutriafol, penconazole, difenoconazole, prothioconazole, epoxiconazole, mefentrifluconazole, triticonazole, imazalil, prochloraz, lobutanii, azaconazole, etaconazole, bitertanol, fluquinconazole, myclobutanil, flusilazole, cyproconazole, triadimenol, hexaconazole, simeconazole, imibenconazole, diniconazole, pyrisoxazole and any combination thereof. Each alternative represents a separate embodiment.

[0059] In some embodiments, the DMI is prothioconazole. In some embodiments, the DMi is tebuconazole.

[0060] In some embodiments, the phenyl amide fungicide is selected from the group consisting of benalaxyl, metalaxyl, kiralaxyl, mefenoxan, metalaxyl-M and any combination thereof. Each alternative represents a separate embodiment.

[0061] In some embodiments, the OSBPI fungicide is selected from the group consisting of fluoxapiprolin, oxathiapiprolin and a combination thereof. Each alternative represents a separate embodiment.

[0062] In some embodiments, the MBC fungicide is selected from the group consisting of carbendazim, thiabendazole, thiophanate-methyl and a combination thereof. Each alternative represents a separate embodiment.

[0063] In some embodiments, the keto -reductase inhibitor fungicide is selected from the group consisting of fenhexamid, fenpyrazamine and a combination thereof. Each alternative represents a separate embodiment.

[0064] In some embodiments the carboxylic acid amide fungicide is selected from the group consisting of benthiavaiicarb, dimethomorph, iprovaiicard, mandipropamid, valifenalate and any combination thereof. Each alternative represents a separate embodiment.

[0065] In some embodiments, the benzamide fungicide is selected from the group consisting of fluopicolide, fluopimomide, zoxamide and any combination thereof. Each alternative represents a separate embodiment.

[0066] In some embodiments, the benzamide fungicide is fluopicolide. In some embodiments, the benzamide fungicide is fluopimomide. In some embodiments, the benzamide fungicide is zoxamide.

[0067] In some embodiments, the phenylpyrrole fungicide is selected from the group consisting of fludioxonil, fenpiclonil and a combination thereof. Each alternative represents a separate embodiment.

[0068] In some embodiments, the aryl phenyl-ketone fungicide is selected from the group consisting of metrafenone, pyriofenone and any combination thereof.

[0069] In some embodiments, the amine fungicide is selected from the group consisting of fenpropidin, spiroxamine and any combination thereof. In some embodiments, the amine fungicide is a morpholine fungicide. In some embodiments, the morpholine is fenpropimorph. Each alternative represents a separate embodiment.

[0070] In some embodiments, the dinitro aniline fungicide is selected from the group consisting of fluazinam, 2, 6- dinitro-aniline fungicide, and a combination thereof. Each alternative represents a separate embodiment.

[0071] In some embodiments, the azanaphthalene fungicide is proquinazid.

[0072] In some embodiments, the benzothiadiazole fungicide is acibenzolar-S-methyl.

[0073] In some embodiments, the carbamate fungicide is selected from the group consisting of propamocarb, iodocarb, prothiocarb and any combination thereof. Each alternative represents a separate embodiment.

[0074] In some embodiments, the cyanoacetamideoxime fungicide is cymoxanil.

[0075] In some embodiments, the dinitrophenyl-crotonate fungicide is meptyldinocap.

[0076] In some embodiments, the glucopyranosyl antibiotic fungicide is validamycin.

[0077] In some embodiments, the tetrazolyloxime fungicide is picarbutrazox.

[0078] In some embodiments, the thiazolidine fungicide is flutianil.

[0079] In some embodiments, the thiophenecarboxamide fungicide is silthiofam.

[0080] In some embodiments, the natural fungicide is laminarin.

[0081] In some embodiments, the phenylacetamide fungicide is cyflufenamide.

[0082] In some embodiments, the phenyl urea fungicide is pencycuron.

[0083] In some embodiments, the polyene fungicide is natamycin.

[0084] In some embodiments, the pyr-hydrazone fungicide is ferimzone.

[0085] In some embodiments, the pyrimidinamine fungicide is diflumetorim.

[0086] in some embodiments, the anilinopyrimidine fungicide is seiected from the group consisting of cyprodinil, mepanipyrim, pyrimethanil and any combination thereof. Each alternative represents a separate embodiment.

[0087] in some embodiments, the hydroxy-(2-amino)-pyrimidines fungicide is selected from the group consisting of bupirimate, dimethirimol, ethirimol and any combination thereof. Each alternative represents a separate embodiment.

[0088] in some embodiments, the fungicide (B) is selected from the group consisting of tebufloquin, tolprocarb, dichlobentiazox, aminopyrifen, dipymetitrone and any combination thereof. Each alternative represents a separate embodiment.

[0089] In some embodiments, the phosphonate fungicide is selected from the group consisting of fosetyl-AI (aluminum triethyl phosphonate), K-phosphonate, phosphorous acid and salts thereof, like disodium phosphonate (sodium phosphite), and esters thereof, like ethyl phosphonate and sodium ethyl phosphonate, and any combination thereof. Each alternative represents a separate embodiment.

[0090] In some embodiments, the phosphonate fungicide is phosphorous acid and its (alkali metal or alkaline earth metal) salts such as potassium phosphites (e.g. KH2PO3 and K2HPO3, LI2HPO3), sodium phosphites such as disodium hydrogen phosphite and monosodium dihydrogen phosphite, ammonium phosphites, and (C-C4) alkyl esters of phosphorous acid and their salts such as aluminum ethyl phosphite (fosetyl-AI), calcium ethyl phosphite, magnesium isopropyl phosphite, magnesium isobutyl phosphite, magnesium sec-butyl phosphite, aluminum N-butyl phosphite, and any combination thereof. Each alternative represents a separate embodiment.

[0091] In some embodiments, the salt of the phosphorous acid is an alkali metal salt or alkaline earth metal salt. In some embodiments, the phosphonate fungicide is potassium phosphonate. In some embodiments, the phosphonate fungicide is disodium phosphonate. In some embodiments, the phosphonate fungicide is sodium phosphites.

[0092] In some embodiments, the plant extract fungicide is selected from the group consisting of a fungicide extracted from Melaleuca alternifolia, a fungicide extracted from Swinglea glutinosa, a fungicide extracted Reynoutria sachalinensis, a fungicide extracted from cotyledons of lupine plantlets, a fungicide extracted from plant oil(s), and any combination thereof. Each alternative represents a separate embodiment.

[0093] In some embodiments, the plant oil is selected from the group consisting of eugenol, geraniol, thymol and any combination thereof.

[0094] In some embodiments, plant extracted fungicide is selected from the group consisting of terpene hydrocarbons, terpene alcohol, terpene phenols and any combination thereof.

[0095] In some embodiments, the plant oil is a mixture of at least two terpenes selected from the group consisting of eugenol, geraniol, thymol, eucalyptol, eugenol, geraniol, myrcene, limonene, linalool, pinene, terpineol, thymol and combination thereof.

[0096] in some embodiments, the plant oil is a mixture of eugenol, geraniol, thymol or combination thereof.

[0097] In some embodiments, the heteroaromatics is etridiazole.

[0098] In some embodiments, the AH fungicide is toiclofos-M.

[0099] In some embodiments, the benzenesulfonamide is flusulfamide.

[0100] In some embodiments, the dicarboximide is selected from iprodione and procymidone.

[0101] In some embodiments, the dithiolane is isoprothiolane.

[0102] In some embodiments, the growth regulator is selected from ethephon and paclobutrazol.

[0103] In some embodiments, the guanidine is dodine and dodine free base.

[0104] In some embodiments, the hexopyranosyl antibiotic is kasugamycin.

[0105] In some embodiments, the MBI-R is tricyclazole.

[0106] In some embodiments, the microbial is Bacillus subtilis, Bacillus subtilis strain Q.ST713.

[0107] In some embodiments, the N-phenyl carbamate is diethofencarb.

[0108] In some embodiments, the organo tin compound is fentin, fentin acetate, fentin hydroxide.

[0109] In some embodiments, the tetracycline antibiotic is oxytetracycline.

[0110] In some embodiments, the uncoupler of oxidative phosphorylation is dinocap.

[0111] In some embodiments, the mixture comprises compound I selected from a group consisting of (1) 4-(Hydroxymethyi)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- (methylaminoj-l-(p-tolylsulfonylamino)l-propene and (5) [p-(3-Methylureidosulfonyljphenyljmethanol and fluxapyroxad.

[0112] 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-imino-3- (methylamino)-l-(p-tolylsulfonylamino)l-propene and (5) [p-(3-Methylureidosulfonyl)phenyl]methanol and prothioconazole.

[0113] 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-methyi-l-[(4-methylphenyi)suifonyi], (4) (E)-2-fiuoro-3-lmino-3- (methyiamino)-l-(p-toiylsuifonylamino)l-propene and (5) [p-(3-Methylureidosulfonyi)phenyl]methanol and foipet.

[0114] In some embodiments, the mixture comprises compound I selected from a group consisting of (1) 4-(Hydroxymethyl)benzene-l-suifinic 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-methyi-l-[(4-methylphenyl)suifonyl], (4) (E)-2-fluoro-3-lmino-3- (methyiamino)-l-(p-tolylsuifonylamino)l-propene and (5) [p-(3-Methylureidosulfonyljphenyijmethanol and captan.

[0115] 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)suifonyl)-4-imino-3-methyl-3,4-dihydropyrimidin-2(lH)-one, (3) 2,4- Pyrimidinedione, 5-fluoro-3-methyl-l-[(4-methylphenyl)su!fonyl], (4) (E)-2-fluoro-3-lmino-3- (methylamino)-l-(p-tolylsulfonylamino)l-propene and (5) [p-(3-Methylureidosulfonyi)phenyl]methanol and azoxystrobin.

[0116] 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)suifonyl], (4) (E)-2-fluoro-3-lmino-3- (methylamino)-l-(p-tolylsulfonylamino)l-propene and (5) [p-(3-Methylureidosulfonyl)pheny!]methanol and picoxystrobin.

[0117] 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)suifonyl)-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-tolyisulfonylamino)l-propene and (5) [p-(3-Methylureidosulfony!)phenyl]methanol and mancozeb.

[0118] 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)suifonyl], (4) (E)-2-fluoro-3-lmino-3- (methyiamino)-l-(p-tolylsuifonylamino)l-propene and (5) [p-(3-Methylureidosulfonyi)phenyl]methanol and mefentrifluconazole.

[0119] 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-toiylsulfonylamino)l-propene and (5) [p-(3-Methylureidosulfonyl)phenyl]methanol and metconazole.

[0120] 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-methyi-l-[(4-methylphenyi)sulfonyi], (4) (E)-2-fiuoro-3-lmino-3- (methylamino)-l-(p-toiylsulfonylamino)l-propene and (5) [p-(3-Methylureidosulfonyi)phenyl]methanol and fluopicolide.

[0121] The present invention provides a mixture comprising (a) Flumetylsulforim metabolite 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.

[0122] The present invention provides a mixture comprising (a) 5-fluoro-4-imino-3-methyl- 3,4-dihydropyrimidin-2(lH)-one, 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.

[0123] In some embodiments, compound I is 4-(Hydroxymethyl)benzene-l-sulfinic acid.

[0124] 4-(Hydroxymethyl)benzene-l-sulfinic acid has the following structure A:

[0125] 4-(Hydroxymethyl)benzene-l-sulfinic acid has an NMR spectrum substantially in accordance with the spectrum as shown in figure 1.

[0126] In some embodiments, the compound I having structure A may be prepared as disclosed in the following scheme 1:

[0127] In some embodiments, compound is 5-fluoro-l-((4-(hydroxymethyl)phenyl)sulfonyl)-4-imino-3-methyl-3,4-dihydropyrimidin-2(lH)-one.

[0128] 5-fluoro-l-((4-(hydroxymethyl)phenyl)sulfonyl)-4-imino-3-methyl-3,4- dihydropyrimidin-2(lH)-one has the following structure B:

[0129] 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 2.

[0130] in some embodiments, compound having structure B may be prepared as disclosed in the following scheme 2:

[0131] In some embodiments, compound I is 2,4-Pyrimidinedione, 5-fluoro-3-methyl-l-[(4- methylphenyi)sulfonyi].

[0132] 2,4-Pyrimidinedione, 5-fluoro-3-methyl-l-[(4-methylphenyl)sulfonyl] has the following structure C:

[0133] 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 3.

[0134] Any one or any combination of the peaks fragments shown in figure 3 may be used to identify 2,4-Pyrimidinedione, 5-fluoro-3 -methyl -l-[(4-methyiphenyi)sulfonyi].

[0135] 2,4-Pyrimidinedione, 5-fluoro-3-methyl-l-[(4-methylphenyi)sulfonyi] may be identified using one of the peaks fragments shown in figure 3. 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.

[0136] 2,4-Pyrimidinedione, 5-fluoro-3-methyl-l-[(4-methylphenyi)sulfonyi] may be identified using two of the peaks shown in figure 3.

[0137] 2,4-Pyrimidinedione, 5-fluoro-3-methyl-l-[(4-methylphenyl)sulfonyl] may be identified using three of the peaks fragments shown in figure 3.

[0138] 2,4-Pyrimidinedione, 5-fluoro-3-methyi-l-[(4-methylphenyl)sulfonyl] may be identified using four of the peaks fragments shown in figure 3.

[0139] For example, 2,4-Pyrimidinedione, 5-fluoro-3-methyl-l-[(4-methylphenyi)sulfonyi] 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] + ).

[0140] 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] + ).

[0141] In some embodiments, compound I having structure C may be prepared as disclosed in the following scheme 3:

[0142] In some embodiments, compound I is E)-2-fluoro-3-lmino-3-(methyiamino)-l-(p- tolylsulfonylamino)l-propene.

[0143] (E)-2-fluoro-3-lmino-3-(methylamino)-l-(p-tolylsulfonylamino)l-propene has the following structure D:

[0144] (E)-2-fluoro-3-lmino-3-(methyiamino)-l-(p-tolylsulfonylamino)l-propene has anNMR spectrum substantially in accordance with the spectrum in figure 4.

[0145] In some embodiments, compound I having structure D may be prepared as disclosed in the following scheme 4:

[0146] In some embodiments, compound I is [p-(3-Methylureidosulfonyl)phenyl]methanol.

[0147] [p-(3-Methylureidosulfonyl)phenyi]methanol has the following structure E:

[0148] [p-(3-Methylureidosulfonyl)phenyl]methanol has an NMR spectrum substantially in accordance with the spectrum of figure 5.

[0149] In some embodiments, compound I having structure E may be prepared as disclosed in the following scheme 5:

[0150] 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.

[0151] In some embodiments, compound I is produced synthetically.

[0152] In some embodiments, compound I is free of plant material and / or biological material (such as tissue).

[0153] Compound(s) I may be present as impurities in a batch of flumetylsulforim or in a mixture or composition comprising an agricultural compound and 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 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 flumetylsulforim or mixtures or compositions comprising an agricultural compound described herein and flumetylsulforim and for presence of these compounds and amounts thereof.

[0154] Compound(s) I may be present as impurities in a batch of flumetylsulforim or in a mixture or composition comprising flumetylsulforim. Flumetylsulforim can be prepared for example as described in international application publication Nos. WO2013 / 025795 and W02021 / 059160.

[0155] in some embodiments, the mixture is a tank mix.

[0156] The components of the mixture of the present invention can be applied either separately or as part of a multipart system.

[0157] 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 pentachiorophenoxide, spiroxamine, sulfur, SYP-Z048, tar oils, tebuconazole, tebufloquin, tecnazene, tetraconazole, thiabendazole, thifluzamide, thiophanate-methyl, thiram, tiadinil, tolclofos-methyl, tolylfluanid, triadimefon, triadimenoi, triazoxide, tricyciazole, 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 -yljethanol, 2,3-dihydro-5-phenyi-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, benodanii, benquinox, bentaluron, benzamacril; benzamacril-isobutyi, benzamorf, binapacryl, bis(methyimercury) 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, myclozoiin, 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, pyracarboiid, 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.

[0158] In some embodiments, the mixture of the present invention further comprises flumetylsulforim.

[0159] In some embodiments, the present invention provides a mixture comprising flumetylsulforim, compound I and an agricultural compound as described herein.

[0160] The present invention also provides a Flumetylsulforim mixture comprises 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 .

[0161] in some embodiments, the Flumetyisulforim mixture comprises 2 or more of compound i seiected 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-methylphenyi)sulfonyi], (4) (E)-2- fluoro-3-lmino-3-(methylamino)-l-(p-tolylsulfonylamino)l-propene and (5) [p-(3-Methylureidosulfonyi)phenyl]methanol.

[0162] in some embodiments, the mixtures of the present invention are in the form of a composition comprising (a) agricultural material, 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-methyi-l-[(4-methylphenyl)sulfonyl], (4) (E)-2-fiuoro-3-lmino-3- (methylamino)-l-(p-tolylsulfonylamino)l-propene and (5) [p-(3-Methylureidosulfonyl)phenyl]methanol.

[0163] The present invention provides a composition comprising (a) agricultural material, 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.

[0164] The agricultural material is as described herein, for example a fungicide.

[0165] In some embodiments, the fungicide is selected from a group consisting of multi-site contact fungicide, Qil fungicide (quinone inside inhibitors), Qol fungicide (quinone outside inhibitors), QoSI fungicide (quinone outside stigmatellin subsite inhibitors), SDHI fungicide (succinate dehydrogenase inhibitors), Demethylation Inhibitor fungicide, phenyl amide fungicide, methyl-benzimidazole-carbamate (MBC) fungicide, carboxylic acid amide fungicide, benzamide fungicide, natural fungicide, anilinopyrimidine fungicide, hydroxy-(2-amino)- pyrimidines fungicide, phosphonate fungicide, plant extract fungicide, Keto-Reductase inhibitor fungicide, phenylpyrrole fungicide (PP), aryl phenyl-ketone fungicide, amine fungicide, dinitro aniline fungicide, azanaphthalene fungicide, benzothiadiazole fungicide, carbamate fungicide, cyanoacetamideoxime fungicide, dinitrophenyl-crotonate fungicide, glucopyranosyl antibiotic fungicide, tetrazolyloxime fungicide, thiazolidine fungicide, oxysterol binding protein inhibitor (OSBPI) fungicide, thiophenecarboxamide fungicide, phenylacetamide fungicide, phenyl urea fungicide, polyene fungicide, pyr-hydrazone fungicide, pyrimidinamine fungicide, pyrimidinone fungicide, fungicide (B), heteroaromatics, aromatic hydrocarbons (AH fungicides), quinoxyfen, benzenesulfonamides, probenazole, tridemorph, iprovalicarb, dicarboximides, dithiolanes, growth regulators, guanidine, fluoxythioconazole, ipfentrifluconazole, triadimefon, triflumizole, hexopyranosyl antibiotics, bordeaux-mixture, benomyl, Melanin Biosynthesis Inhibitors - Reductase (MBI-R), microbials, n-phenyl carbamates, organo tin compounds, oxadixyl, potassium-bicarbonate, potassiumcarbonate, polyoxins, fenamidone, metarylpicoxamid, tetracycline antibiotics, uncouplers of oxidative phosphorylation, chlorinconazide, flufenoxadiazam, ipflufenoquin, pyridachlometyl,propamocarb-HCI, propiconazole and benthiavalicarb-isopropyl. Each genus encompasses the species as described in the present application.

[0166] 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.

[0167] The formulations that are applied most often are aqueous suspensions or emulsions. Either such water-soluble, water suspendable, or emulsifiable formulations are solids, usually known as wettable powders, or liquids, usually known 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.

[0168] 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.

[0169] 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.

[0170] In some embodiments, the composition comprises Flumetylsulforim and agricultural acceptable carrier such as water and / or organic solvent.

[0171] 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.

[0172] 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.

[0173] 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.

[0174] In particular, the composition is effective in controlling a variety of undesirable fungi that infect useful plant crops. The mixtures and compositions disclosed herein may be applied to control and / or prevent a variety of fungal pathogen and diseases associated therewith. Insome 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.

[0175] 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.

[0176] In some embodiments, the fungal disease is one of Leaf Blotch of Wheat (Mycosphaerella graminicola; anamorph: Septoria tritici), Wheat Brown Rust (Puccinia triticina), Stripe Rust (Puccinia striiformis f, sp. tritici), Scab of Apple (Venturia inaequalis), Blister Smut of Maize (Ustilago maydis), Powdery Mildew of Grapevine (Uncinula necator), Barley scald (Rhynchosporium secalis), Blast of Rice (Magnaporthe grisea), Rust of Soybean (Phakopsora pachyrhizi), Glume Blotch of Wheat (Leptosphaeria nodorum), Powdery Mildew of Wheat (Blumeria graminis f. sp.tritici), Powdery Mildew of Barley (Blumeria graminis f. sp. 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).

[0177] 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.

[0178] 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).

[0179] 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 triticaie. 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.

[0180] In another embodiment, the crop plants are dicotyledonous plants.

[0181] In one embodiment, 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.

[0182] The present invention further includes within its scope the use of the mixture or composition disclosed herein for treating a plant or locus against fungal infection. The present mixtures 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.

[0183] 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.

[0184] The present invention provides use of at least one of the mixtures disclosed herein as reference standard (1) for determining purity and / or metabolite profile of Flumetylsulforim, (2) for determining purity of a composition comprising Flumetylsulforim, (3) to test for its presence and / or quantity in 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 Flumetylsulforim was applied and / or (6) to test for its presence and / or quantity in a plant to which Flumetylsulforim was applied.

[0185] The present invention provides use of at least one Compound I Mix(es) as reference standard (1) for determining purity and / or metabolite profile of Flumetylsulforim, (2) for determining purity of a composition comprising Flumetylsulforim, (3) to test for its presence and / or quantity in 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 Flumetylsulforim was applied and / or (6) to test for its presence and / or quantity in a plant to which Flumetylsulforim was applied.

[0186] The subject invention is further directed to use of Compound I Mix(es) as reference standard for determining purity and / or metabolite profile of a mixture comprising Flumetylsulforim.

[0187] in some embodiments, the Compound i Mix comprises compound I having the structure A as describe herein.

[0188] in some embodiments, the Compound i Mix comprises compound I having the structure A and an agricultural compound as described herein, that is used as reference standard for determining purity and / or metabolite profile of a mixture comprising Flumetylsulforim and the same agricultural compound.

[0189] in some embodiments, the Compound i Mix comprises compound I having the structure B as describe herein.

[0190] in some embodiments, the Compound i Mix comprises compound I having the structure B and an agricultural compound as described herein, that is used as reference standard for determining purity and / or metabolite profile of a mixture comprising Flumetylsulforim and the same agricultural compound.

[0191] in some embodiments, the Compound I Mix comprises compound I having the structure C as describe herein.

[0192] in some embodiments, the Compound I Mix comprises compound I having the structure C and an agricultural compound as described herein, that is used as reference standard for determining purity and / or metabolite profile of a mixture comprising Flumetylsulforim and the same agricultural compound.

[0193] In some embodiments, the Compound I Mix comprises compound I having the structure D as describe herein.

[0194] In some embodiments, the Compound I Mix comprises compound I having the structure D and an agricultural compound as described herein, that is used as reference standard for determining purity and / or metabolite profile of a mixture comprising Flumetylsulforim and the same agricultural compound.

[0195] In some embodiments, the Compound I Mix comprises compound I having the structure E as describe herein.

[0196] In some embodiments, the Compound I Mix comprises compound I having the structure E and an agricultural compound as described herein, that is used as reference standard for determining purity and / or metabolite profile of a mixture comprising Flumetylsulforim and the same agricultural compound.

[0197] The present invention provides use of Compound I Mix(es) as reference standard for determining the purity of a composition comprising a Flumetylsulforim mixture.

[0198] In some embodiments, the Compound I Mix comprises compound I having the structure A as describe herein.

[0199] In some embodiments, the Compound I Mix comprises compound I having the structure A and an agricultural compound as described herein, that is used as referencestandard for determining the purity of a composition comprising a Flumetyisulforim and the same agricultural compound.

[0200] In some embodiments, the Compound I Mix comprises compound I having the structure B as describe herein.

[0201] In some embodiments, the Compound I Mix comprises compound I having the structure B and an agricultural compound as described herein, that is used as reference standard for determining the purity of a composition comprising a Flumetyisulforim and the same agricultural compound.

[0202] In some embodiments, the Compound I Mix comprises compound I having the structure C as describe herein.

[0203] In some embodiments, the Compound I Mix comprises compound I having the structure C and an agricultural compound as described herein, that is used as reference standard for determining the purity of a composition comprising a Flumetyisulforim and the same agricultural compound.

[0204] In some embodiments, the Compound I Mix comprises compound I having the structure D as describe herein.

[0205] In some embodiments, the Compound I Mix comprises compound I having the structure D and an agricultural compound as described herein, that is used as reference standard for determining the purity of a composition comprising a Flumetyisulforim and the same agricultural compound.

[0206] In some embodiments, the Compound I Mix comprises compound I having the structure E as describe herein.

[0207] In some embodiments, the Compound I Mix comprises compound I having the structure E and an agricultural compound as described herein, that is used as reference standard for determining the purity of a composition comprising a Flumetyisulforim and the same agricultural compound.

[0208] The present invention provides use of Compound I Mix(es) as a reference standard to test for the presence and / or quantity of the compound I in a Flumetyisulforim mixture.

[0209] In some embodiments, the Compound I Mix comprises compound I having the structure A as describe herein.

[0210] In some embodiments, the Compound I Mix comprises compound I having the structure A and an agricultural compound as described herein, that is used as reference standard to test for the presence and / or quantity of the compound I in a mixture comprising Flumetyisulforim and the agricultural compound.

[0211] In some embodiments, the Compound I Mix comprises compound I having the structure B as describe herein.[□2.12] in some embodiments, the Compound i Mix comprises compound I having the structure B and an agricuiturai compound as described herein, that is used as reference standard to test for the presence and / or quantity of the compound I in a mixture comprising Fiumetylsulforim and the agricultural compound.

[0213] In some embodiments, the Compound I Mix comprises compound I having the structure C as describe herein.

[0214] In some embodiments, the Compound I Mix comprises compound I having the structure C and an agricultural compound as described herein, that is used as reference standard to test for the presence and / or quantity of the compound I in a mixture comprising Fiumetylsulforim and the agricultural compound.

[0215] In some embodiments, the Compound I Mix comprises compound I having the structure D as describe herein.

[0216] In some embodiments, the Compound I Mix comprises compound I having the structure D and an agricultural compound as described herein, that is used as reference standard to test for the presence and / or quantity of the compound I in a mixture comprising Fiumetylsulforim and the agricultural compound.

[0217] In some embodiments, the Compound I Mix comprises compound I having the structure E as describe herein,

[0218] In some embodiments, the Compound I Mix comprises compound I having the structure E and an agricultural compound as described herein, that is used as reference standard to test for the presence and / or quantity of the compound I in a mixture comprising Fiumetylsulforim and the agricultural compound.

[0219] The present invention provides use of Compound I Mix(es) as a reference standard to test for the presence and / or quantity of the compound I in a composition.

[0220] In some embodiments, the Compound I Mix comprises compound I having the structure A as describe herein.

[0221] In some embodiments, the Compound I Mix comprises compound I having the structure A and an agricultural compound as described herein, that is used as reference standard to test for the presence and / or quantity of the compound I in a composition.

[0222] In some embodiments, the Compound I Mix comprises compound I having the structure B as describe herein.

[0223] In some embodiments, the Compound I Mix comprises compound I having the structure B and an agricultural compound as described herein, that is used as reference standard to test for the presence and / or quantity of the compound I in a composition.

[0224] In some embodiments, the Compound I Mix comprises compound I having the structure C as describe herein.T1[□225] in some embodiments, the Compound i Mix comprises compound I having the structure C and an agricuiturai compound as described herein, that is used as reference standard to test for the presence and / or quantity of the compound I in a composition.

[0226] in some embodiments, the Compound i Mix comprises compound I having the structure D as describe herein.

[0227] in some embodiments, the Compound i Mix comprises compound I having the structure D and an agricultural compound as described herein, that is used as reference standard to test for the presence and / or quantity of the compound i in a composition.

[0228] in some embodiments, the Compound i Mix comprises compound I having the structure E as describe herein.

[0229] in some embodiments, the Compound i Mix comprises compound I having the structure E and an agricultural compound as described herein, that is used as reference standard to test for the presence and / or quantity of the compound i in a composition.

[0230] in some embodiments, the composition is a composition comprising Flumetylsulforim mixture as described herein.

[0231] The present invention provides use of Compound i Mix(es) as reference standard to test for the presence and / or quantity of the compound I at a locus where Flumetylsulforim mixture was applied.

[0232] in some embodiments, the Compound i Mix comprises compound I having the structure A as describe herein.

[0233] in some embodiments, the Compound i Mix comprises compound I having the structure A and an agricultural compound as described herein, that is used as reference standard to test for the presence and / or quantity of the compound I at a locus where Flumetylsulforim mixture was applied.

[0234] In some embodiments, the Compound I Mix comprises compound I having the structure B as describe herein.

[0235] In some embodiments, the Compound I Mix comprises compound I having the structure B and an agricuiturai compound as described herein, that is used as reference standard to test for the presence and / or quantity of the compound I at a locus where Flumetylsulforim mixture was applied.

[0236] In some embodiments, the Compound I Mix comprises compound I having the structure C as describe herein.

[0237] In some embodiments, the Compound I Mix comprises compound I having the structure C and an agricuiturai compound as described herein, that is used as reference standard to test for the presence and / or quantity of the compound I at a locus where Flumetylsulforim mixture was applied.[□238] in some embodiments, the Compound i Mix comprises compound I having the structure D as describe herein.

[0239] in some embodiments, the Compound i Mix comprises compound I having the structure D and an agricultural compound as described herein, that is used as reference standard to test for the presence and / or quantity of the compound i at a locus where Flumetylsuiforim mixture was applied.

[0240] in some embodiments, the Compound i Mix comprises compound I having the structure E as describe herein.

[0241] in some embodiments, the Compound i Mix comprises compound I having the structure E and an agricultural compound as described herein, that is used as reference standard to test for the presence and / or quantity of the compound I at a locus where Flumetylsuiforim mixture was applied.

[0242] in some embodiments, the Flumetylsuiforim mixture comprises the agricultural compound.

[0243] The present invention provide use of Compound I Mix(es) as reference standard to test for the presence and / or quantity of the compound I in a plant to which Flumetylsuiforim mixture was applied.

[0244] In some embodiments, the Compound I Mix comprises compound I having the structure A as describe herein.

[0245] In some embodiments, the Compound I Mix comprises compound I having the structure A and an agricultural compound as described herein, that is used as reference standard to test for the presence and / or quantity of the compound I in a plant to which Flumetylsuiforim mixture comprising the agricultural compound was applied.

[0246] In some embodiments, the Compound I Mix comprises compound I having the structure B as describe herein.

[0247] In some embodiments, the Compound I Mix comprises compound I having the structure B and an agricultural compound as described herein, that is used as reference standard to test for the presence and / or quantity of the compound I in a plant to which Flumetylsuiforim mixture comprising the agricultural compound was applied.

[0248] In some embodiments, the Compound I Mix comprises compound I having the structure C as describe herein.

[0249] In some embodiments, the Compound I Mix comprises compound I having the structure C and an agricultural compound as described herein, that is used as reference standard to test for the presence and / or quantity of the compound I in a plant to which Flumetylsuiforim mixture comprising the agricultural compound was applied.[□250] in some embodiments, the Compound i Mix comprises compound I having the structure D as describe herein.

[0251] in some embodiments, the Compound i Mix comprises compound I having the structure D and an agricultural compound as described herein, that is used as reference standard to test for the presence and / or quantity of the compound I in a plant to which Flumetylsuiforim mixture comprising the agricultural compound was applied.

[0252] in some embodiments, the Compound i Mix comprises compound I having the structure E as describe herein.

[0253] in some embodiments, the Compound i Mix comprises compound I having the structure E and an agricultural compound as described herein, that is used as reference standard to test for the presence and / or quantity of the compound I in a plant to which Flumetylsuiforim mixture comprising the agricultural compound was applied.

[0254] The present invention provides a method for monitoring the stability of a composition comprising Flumetylsuiforim mixture, the method comprising measuring the concentration of Compound I Mix(es) in the composition, wherein increase in the concentration of theCompound I Mix(es), indicates degradation of Flumetylsuiforim mixture.

[0255] In some embodiments, the Compound I Mix(es) is as described herein.

Claims

CLAIMS1. A mixture comprising (a) one or more agricultural material, and (b) one or moreCompound I selected from a group consisting of (1) 4-(Hydroxymethyi)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)phenyf]methanol.

2. The mixture of claim 1, wherein the agricultural material is selected from an agrochemical, plant growth regulator, a bio-stimulant, a hormone and agriculturally acceptable additive.

3. The mixture of claim 1 or 2, wherein the agrochemical is a pesticide.

4. The mixture of any one of claims 1-3, wherein the pesticide is a fungicide.

5. The mixture of claim 4, wherein the fungicide is selected from a group consisting of multi-site contact fungicide, Qil fungicide (quinone inside inhibitors), Qol fungicide (quinone outside inhibitors), QoSI fungicide (quinone outside stigmatellin subsite inhibitors), SDHI fungicide (succinate dehydrogenase inhibitors), Demethylation Inhibitor fungicide, phenyl amide fungicide, methyl-benzimidazole-carbamate (MBC) fungicide, carboxylic acid amide fungicide, benzamide fungicide, natural fungicide, anilinopyrimidine fungicide, hydroxy-(2- amino)-pyrimidines fungicide, phosphonate fungicide, plant extract fungicide, Keto- Reductase inhibitor fungicide, phenylpyrrole fungicide (PP), aryl phenyl-ketone fungicide, amine fungicide, dinitro aniline fungicide, azanaphthalene fungicide, benzothiadiazole fungicide, carbamate fungicide, cyanoacetamideoxime fungicide, dinitrophenyl-crotonate fungicide, glucopyranosyl antibiotic fungicide, tetrazolyloxime fungicide, thiazolidine fungicide, oxysterol binding protein inhibitor (OSBPI) fungicide, thiophenecarboxamide fungicide, phenylacetamide fungicide, phenyl urea fungicide, polyene fungicide, pyr- hydrazone fungicide, pyrimidinamine fungicide, pyrimidinone fungicide, fungicide (B), heteroaromatics, aromatic hydrocarbons (AH fungicides), quinoxyfen, benzenesulfonamides, probenazole, tridemorph, iprovalicarb, dicarboximides, dithiolanes, growth regulators, guanidine, fluoxythioconazole, ipfentrifluconazole, triadimefon, triflumizole, hexopyranosyl antibiotics, bordeaux-mixture, benomyl, Melanin Biosynthesis Inhibitors - Reductase (MBI-R), microbials, n-phenyl carbamates, organo tin compounds, oxadixyl, potassium-bicarbonate, potassium-carbonate, polyoxins, fenamidone, metarylpicoxamid, tetracycline antibiotics, uncouplers of oxidative phosphorylation, chlorinconazide, flufenoxadiazam, ipflufenoquin, pyridachlometyl, propamocarb-HCI, propiconazole and benthiavalicarb-isopropyl.

6. The mixture of claim 5, wherein the multi-site contact fungicide is selected from a group consisting of phthalimides, thiocarbamate, maleimide, quinoxalines, quinones, triazines, bis-guanidines, sulfamides, chloronitriles, dithio-carbamates, inorganic fungicide and any combination thereof.

7. The mixture of claim 5, wherein the Qil is selected from the group consisting of amisulbrom, cyazofamid, fenpicoxamid and any combination thereof.

8. The mixture of claim 5, wherein the Qol is selected from the group consisting of azoxystrobin, kresoxim-methyl, picoxystrobin, fluxastrobin, dimoxystrobin, pyraclostrobin, trifloxystrobin, coumoxystrobin, fenaminstrobin, pyrametostrobin, triclopyricarb, pyribencarb, pyraoxystrobin, metyltetraprole, mandestrobin, famoxadone, oryzastrobin, enoxastrobin, pyraclostrobin, fluoxastrobin, flufenostrin, flufenoxystrobin, metominostrobin, triclopyricarb; pyriminostrobin, florylpicoxamid, and any combination thereof.

9. The mixture of claim 5, wherein the the QoSI is ametoctradin.

10. The mixture of claim 5, wherein the SDHI fungicide is selected from the group consisting of fluxapyroxad, penflufen, bixafen, isopyrazam, sedaxane, benzovindiflupyr, thifluzamide, isofetamid, fluopyram, pydiflumetofen, pyraziflumid, flutolanil, carboxin, boscalid, fluindapyr, penthiopyrad, isoflucypram inpyrfluxam, furametpyr, benodanil, mepronil, fenfuram, oxycarboxin, pyrapropoyne, flubeneteram, quinofumelin and any combination thereof.

11. The mixture of claim 5, wherein the DMI fungicide is selected from the group consisting of ipconazole, tebuconazole, metconazole, fenbuconazole, bromuconazole, tetraconazole, flutriafol, penconazole, difenoconazole, prothioconazole, epoxiconazole, mefentrifluconazole, triticonazole, imazalil, prochloraz, lobutanil, azaconazole, etaconazole, bitertanol, fluquinconazole, myclobutanil, flusilazole, cyproconazole, triadimenol, hexaconazole, simeconazole, imibenconazole, diniconazole, pyrisoxazole and any combination thereof.

12. The mixture of claim 5, wherein, the phenyl amide fungicide is selected from the group consisting of benalaxyl, metalaxyl, kiralaxyl, mefenoxan, metalaxyl-M and any combination thereof.

13. The mixture of claim 5, wherein the MBC fungicide is selected from the group consisting of carbendazim, thiabendazole, thiophanate-methyl and a combination thereof.

14. The mixture of claim 5, wherein the carboxylic acid amide fungicide is selected from the group consisting of benthiavalicarb, dimethomorph, iprovalicard, mandipropamid, valifenalate and any combination thereof.

15. The mixture of claim 5, wherein the benzamide fungicide is selected from the group consisting of fluopicolide, fluopimomide, zoxamide and any combination thereof.

16. The mixture of claim 5, wherein the natural fungicide is laminarin.

17. The mixture of claim 5, wherein the anilinopyrimidine fungicide is selected from the group consisting of cyprodinil, mepanipyrim, pyrimethanil and any combination thereof.

18. The mixture of claim 5, wherein the hydroxy-(2-amino)-pyrimidines fungicide is selected from the group consisting of bupirimate, dimethirimol, ethirimol and any combination thereof.

19. The mixture of claim 5, wherein the phosphonate fungicide is selected from the group consisting of fosetyl-AI (aluminum triethyl phosphonate), K-phosphonate, phosphorous acid and salts thereof, like disodium phosphonate (sodium phosphite), and esters thereof, like ethyl phosphonate and sodium ethyl phosphonate, and any combination thereof.

20. The mixture of claim 5, wherein the plant extract fungicide is selected from the group consisting of a fungicide extracted from Melaleuca alternifolia, a fungicide extracted from Swinglea glutinosa, a fungicide extracted from Reynoutria sachalinensis, a fungicide extracted from cotyledons of lupine plantlets, a fungicide extracted from plant oil(s), terpene hydrocarbons, terpene alcohol, terpene phenols and any combination thereof.

21. The mixture of claim 5, wherein the keto-reductase inhibitor fungicide is selected from the group consisting of fenhexamid, fenpyrazamine and a combination thereof.

22. The mixture of claim 5, wherein the phenylpyrrole fungicide is selected from the group consisting of fludioxonil, fenpiclonil and a combination thereof.

23. The mixture of claim 5, wherein the aryl phenyl-ketone fungicide is selected from the group consisting of metrafenone, pyriofenone and any combination thereof.

24. The mixture of claim 5, wherein the amine fungicide is selected from the group consisting of fenpropidin, spiroxamine, morpholine and any combination thereof.

25. The mixture of claim 5, wherein the dinitro aniline fungicide is selected from the group consisting of fluazinam, 2, 6- dinitro-aniline fungicide, and a combination thereof.

26. The mixture of claim 5, wherein the azanaphthalene fungicide is proquinazid.

27. The mixture of claim 5, wherein the benzothiadiazole fungicide is acibenzolar-S- methyl.

28. The mixture of claim 5, wherein the carbamate fungicide is selected from the group consisting of propamocarb, iodocarb, prothiocarb and any combination thereof.

29. The mixture of claim 5, wherein the cyanoacetamideoxime fungicide is cymoxanil.

30. The mixture of claim 5, wherein the dinitrophenyl-crotonate fungicide is meptyldinocap.

31. The mixture of claim 5, wherein the glucopyranosyl antibiotic fungicide is validamycin.

32. The mixture of claim 5, wherein the tetrazolyloxime fungicide is picarbutrazox.

33. The mixture of claim 5, wherein the thiazolidine fungicide is flutianil.

34. The mixture of claim 5, wherein the OSBPI fungicide is selected from the group consisting of fluoxapiprolin, oxathiapiprolin and a combination thereof.

35. The mixture of claim 5, wherein the thiophenecarboxamide fungicide is silthiofam.

36. The mixture of claim 5, wherein the phenylacetamide fungicide is cyflufenamide.

37. The mixture of claim 5, wherein the phenyl urea fungicide is pencycuron.

38. The mixture of claim 5, wherein the polyene fungicide is natamycin.

39. The mixture of claim 5, wherein the pyr-hydrazone fungicide is ferimzone.

40. The mixture of claim 5, wherein the pyrimidinamine fungicide is diflumetorim.

41. The mixture of claim 5, wherein heteroaromatics is etridiazole.

42. The mixture of claim 5, wherein the AH fungicides is tolclofos-M.

43. The mixture of claim 5, wherein the benzenesulfonamides is flusulfamide.

44. The mixture of claim 5, wherein the dicarboximide is selected from iprodione and procymidone.

45. The mixture of claim 5, wherein the dithiolane is isoprothiolane.

46. The mixture of claim 5, wherein the growth regulator is selected from ethephon and paclobutrazol.

47. The mixture of claim 5, wherein the guanidine is dodine.

48. The mixture of claim 5, wherein the hexopyranosyl antibiotic is kasugamycin.

49. The mixture of claim 5, wherein the MBI-R is tricyclazole.

50. The mixture of claim 5, wherein the microbial is selected from Bacillus subtilis and Bacillus subtilis strain QST713.

51. The mixture of claim 5, wherein the N-phenyl carbamate is diethofencarb.

52. The mixture of claim 5, wherein the organo tin compound is selected from fentin, fentin acetate and fentin hydroxide.

53. The mixture of claim 5, wherein the tetracycline antibiotic is oxytetracycline.

54. The mixture of claim 5, wherein the uncoupler of oxidative phosphorylation is dinocap.

55. The mixture of any one of claims 1-54, further comprising at least one pesticide.

56. The mixture of any one of claims 1-55, wherein the mixture is a tank mix.

57. A composition comprising the mixture of any one of claims 1-55.

58. Use of the mixture or composition of any one of claims 1-54 for treating a plant or locus against fungal infection.

59. Use of the mixture or composition of any one of claims 1-54 for controlling or preventing a fungal attack.

60. The mixture or composition of any one of claims 1-54 for use to treat a plant or locus against fungal infection.

61. Use of the mixture or composition of any one of claims 1-54 and 57 as reference standard for determining purity and / or metabolite profile of a mixture comprising Flumetylsulforim.

62. Use of the mixture or composition of any one of claims 1-54 and 57 as reference standard for determining the purity of a composition comprising a Flumetylsulforim mixture.

63. Use of the mixture or composition of any one of claims 1-54 and 57 as a reference standard to test for the presence and / or quantity of the compound I in a Flumetylsulforim mixture.

64. Use of the mixture or composition of any one of claims 1-54 and 57 as a reference standard to test for the presence and / or quantity of the compound I in a composition.

65. Use of the mixture or composition of any one of claims 1-54 and 57 as reference standard to test for the presence and / or quantity of the compound I at a locus where Flumetylsulforim mixture was applied.

66. Use of the mixture or composition of any one of claims 1-54 and 57 as reference standard to test for the presence and / or quantity of the compound I in a plant to which Flumetylsulforim mixture was applied.

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