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WO2024028812A1 - 5-fluoro-4-imino-3-méthyl-1-tosyl-3,4-dihydropyrimidin-2 (1h)-one pour champignon résistant aux fongicides - Google Patents

5-fluoro-4-imino-3-méthyl-1-tosyl-3,4-dihydropyrimidin-2 (1h)-one pour champignon résistant aux fongicides Download PDF

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Publication number
WO2024028812A1
WO2024028812A1 PCT/IB2023/057879 IB2023057879W WO2024028812A1 WO 2024028812 A1 WO2024028812 A1 WO 2024028812A1 IB 2023057879 W IB2023057879 W IB 2023057879W WO 2024028812 A1 WO2024028812 A1 WO 2024028812A1
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Prior art keywords
fungal pathogen
fungicide
plant
flumetylsulforim
resistant
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Alexandra ROSENMUND
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Adama Makhteshim Ltd
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Adama Makhteshim Ltd
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Priority to EP23757704.4A priority Critical patent/EP4565066A1/fr
Priority to AU2023318916A priority patent/AU2023318916A1/en
Priority to CA3263912A priority patent/CA3263912A1/fr
Publication of WO2024028812A1 publication Critical patent/WO2024028812A1/fr
Anticipated expiration legal-status Critical
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P3/00—Fungicides
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines

Definitions

  • the present invention provides a method for treating a plant or locus against infection by a fungal pathogen resistant to at least one non-flumetylsulforim fungicide comprising applying an effective amount of flumetylsulforim to the plant or locus so as to thereby treat the plant or locus against infection by the fungal pathogen, wherein the fungal pathogen is other than Zymoseptoria tritici strain Mg Tri-R6.
  • Fungicides are compounds, of natural or synthetic origin, which act to protect plants against damage caused by fungi.
  • Current methods of agriculture rely heavily on the use of fungicides. In fact, some crops cannot be grown usefully without the use of fungicides.
  • Using fungicides allows a grower to increase the yield and the quality of the crop, and consequently, increase the value of the crop. In most situations, the increase in value of the crop is worth at least three times the cost of the use of the fungicide.
  • Flumetylsulforim (5-fluoro-4-imino-3-methyl-l-tosyl-3,4-dihydropyrimidin-2(l//)-one) is a compound of Formula I having the following structure:
  • Flumetylsulforim provides control of a variety of fungal pathogens affecting economically important crops including, but not limited to, the causal agent of leaf blotch in wheat, Zymoseptoria tritici (SEPTTR) and fungi of the classes ascomycetes and basidiomycetes. Flumetylsulforim has both preventive and curative effects.
  • the present invention provides a method for treating a plant or locus against infection by a fungal pathogen resistant to at least one non-flumetylsulforim fungicide comprising applying an effective amount of flumetylsulforim to the plant or locus so as to thereby treat the plant or locus against infection by the fungal pathogen, wherein the fungal pathogen is other than Zymoseptoria tritici strain Mg Tri-R6.
  • the present invention provides a composition comprising flumetylsulforim and an agriculturally acceptable carrier for use in treating a plant or locus against infection by a fungal pathogen resistant to at least one non-flumetylsulforim fungicide, wherein the fungal pathogen is other than Zymoseptoria tritici strain Mg Tri-R6.
  • the present invention provides use of a composition comprising flumetylsulforim and an agriculturally acceptable carrier for treating a plant or locus against infection by a fungal pathogen resistant to at least one non-flumetylsulforim fungicide, wherein the fungal pathogen is other than Zymoseptoria tritici strain Mg Tri-R6.
  • the present invention provides use of flumetylsulforim in the manufacturing of a composition for treating a plant or locus against infection by a fungal pathogen resistant to at least one non- flumetylsulforim fungicide, wherein the fungal pathogen is other than Zymoseptoria tritici strain Mg Tri-R6.
  • the present invention provides a method for treating a seed or seedling against infection by a fungal pathogen resistant to at least one non-flumetylsulforim fungicide comprising applying flumetylsulforim to the seed, seedling and/or a locus thereof so as to thereby treat the seed or seedling against infection by the fungal pathogen.
  • the present invention provides a method of producing a plant resistant to infection by a fungal pathogen resistant to at least one non-flumetylsulforim fungicide, wherein the method comprises applying flumetylsulforim to the plant, a seed of the plant, a seedling of the plant, or a locus thereof so as to thereby produce a plant resistant to infection by the fungal pathogen.
  • the present invention provides a plant resistant to infection by a fungal pathogen resistant to at least one non-flumetylsulforim fungicide, wherein the seed adapted to produce the plant, the seedling adapted to produce the plant, or a locus of plant is treated with flumetylsulforim.
  • the present invention provides a plant seed or seedling adapted to produce a plant resistant to infection by a fungal pathogen resistant to at least one non-flumetylsulforim fungicide, wherein the plant seed or seedling is treated with flumetylsulforim.
  • the present invention provides a mature plant resistant to infection by a fungal pathogen resistant to at least one non-flumetylsulforim fungicide, wherein the mature plant or a seed or seedling adapted to produce the mature plant is treated with an amount of flumetylsulforim, and wherein the treated mature plant has an ecologically acceptable effect on non-target organisms that contact the treated mature plant.
  • Figure 1 Disease assessment (Intensity of infection) on the 2nd leaf blade of wheat plants cv. Alixan untreated (Dark symbols) or treated preventively with ADF-16, penthiopyrad, metconazole, or tebuconazole at 2 rates each, 15 dpi, 21 dpi and 28 dpi, with a pycnospore suspension of Zymoseptoria tritici strain Zt StA, sensible to all fungicides, in controlled conditions.
  • Figure 2 Comparison of the Area Under Disease Progress Curve (AUDPC) obtained from the 15, 24 and 28 dpi intensity of infection of Zymoseptoria tritici strain Zt StA sensible to all fungicides, on the second leaf blade of wheat plantlets cv. Alixan untreated (Dark symbols) or treated preventively with ADF-16, penthiopyrad, metconazole, or tebuconazole at 2 rates each, in controlled conditions.
  • AUDPC Area Under Disease Progress Curve
  • Figure 3 Comparison of the Area Under Disease Progress Curve (AUDPC) obtained from the 15, 24 and 28 dpi intensity of infection of Zymoseptoria tritici strain Zt StA sensible to all fungicides, on the second leaf blade of wheat plantlets cv. Alixan untreated (Dark symbols) or treated preventively with ADF-16, penthiopyrad, metconazole, or tebuconazole at 2 rates each, in controlled conditions.
  • AUDPC Area Under Disease Progress Curve
  • Figure 4 Disease assessment (Intensity of infection) on the 2nd leaf blade of wheat plants cv. Alixan untreated (Dark symbols) or treated preventively with ADF-16, penthiopyrad, metconazole, or tebuconazole at 2 rates each, 15 dpi, 21 dpi and 28 dpi, with pycnospores of the Zymoseptoria tritici strain Zt 61 in controlled conditions.
  • Figure 5 Comparison of the Area Under Disease Progress Curve (AUDPC) obtained from the 15, 24 and 28 dpi intensity of infection of Zymoseptoria tritici strain Zt 61 of the second leaf blade of wheat plantlets cv. Alixan untreated (Dark symbols) or treated preventively with ADF-16, penthiopyrad, metconazole, or tebuconazole at 2 rates each, in controlled conditions.
  • AUDPC Area Under Disease Progress Curve
  • Figure 6 Comparison of the fungicide efficacy, obtained from the AUDPC values of ADF-16, penthiopyrad, metconazole, or tebuconazole at 2 rates each, applied 24 hours before the inoculation of wheat plants cv. ALIXAN with pycnospores of Zymoseptoria tritici strain Zt 61 in controlled conditions.
  • Figure 7 Disease assessment (Intensity of infection) on the 2nd leaf blade of wheat plants cv. Alixan untreated (Dark symbols) or treated preventively with ADF-16, penthiopyrad, metconazole, or tebuconazole at 2 rates each, 15 dpi, 21 dpi and 28 dpi, with pycnospores of the Zymoseptoria tritici strain Zt 99 in controlled conditions.
  • Figure 8 Comparison of the Area Under Disease Progress Curve (AUDPC) obtained from the 15, 24 and 28 dpi intensity of infection of Zymoseptoria tritici strain Zt 99 on the second leaf blade of wheat plantlets cv. Alixan untreated (Dark symbols) or treated preventively with ADF-16, penthiopyrad, metconazole, or tebuconazole at 2 rates each, in controlled conditions.
  • AUDPC Area Under Disease Progress Curve
  • Figure 9 Comparison of the fungicide efficacy, obtained from the AUDPC values of ADF-16, penthiopyrad, metconazole, or tebuconazole at 2 rates each, applied 24 hours before the inoculation of wheat plants cv. ALIXAN with pycnospores of Zymoseptoria tritici strain Zt 99 in controlled conditions.
  • Figure 10 Disease assessment (Intensity of infection) on the 2nd leaf blade of wheat plants cv. Alixan untreated (Dark symbols) or treated preventively with ADF-16, penthiopyrad, metconazole, or tebuconazole at 2 rates each, 15 dpi, 21 dpi and 28 dpi, with pycnospores of the Zymoseptoria tritici strain Zt 19-52 in controlled conditions.
  • Figure 11 Comparison of the fungicide efficacy, obtained from the AUDPC values of ADF-16, penthiopyrad, metconazole, or tebuconazole at 2 rates each, applied 24 hours before the inoculation of wheat plants cv. ALIXAN with pycnospores of Zymoseptoria tritici strain Zt 19-52 in controlled conditions.
  • Figure 12 Disease assessment (Intensity of infection) on the 2nd leaf blade of wheat plants cv. Alixan untreated (Dark symbols) or treated preventively with ADF-16, penthiopyrad, metconazole, or tebuconazole at 2 rates each, 15 dpi, 21 dpi and 28 dpi, with pycnospores of the Zymoseptoria tritici strain Zt 20 in controlled conditions.
  • Figure 13 Comparison of the fungicide efficacy, obtained from the AUDPC values of ADF-16, penthiopyrad, metconazole, or tebuconazole at 2 rates each, applied 24 hours before the inoculation of wheat plants cv.
  • Figure 14 Disease assessment (Intensity of infection) on the 2nd leaf blade of wheat plants cv. Alixan untreated (Dark symbols) or treated preventively with ADF-16, penthiopyrad, metconazole, or tebuconazole at 2 rates each, 15 dpi, 21 dpi and 28 dpi, with pycnospores of the Zymoseptoria tritici strain Zt 38-02 in controlled conditions.
  • Figure 15 Comparison of the Area Under Disease Progress Curve (AUDPC) obtained from the 15, 24 and 28 dpi intensity of infection of Zymoseptoria tritici strain Zt 38-02 on the second leaf blade of wheat plantlets cv. Alixan untreated (Dark symbols) or treated preventively with ADF- 16, penthiopyrad, metconazole, or tebuconazole at 2 rates each, in controlled conditions.
  • AUDPC Area Under Disease Progress Curve
  • Figure 16 Comparison of the fungicide efficacy, obtained from the AUDPC values of ADF-16, penthiopyrad, metconazole, or tebuconazole at 2 rates each, applied 24 hours before the inoculation of wheat plants cv. ALIXAN with pycnospores of Zymoseptoria tritici strain Zt 38-02 in controlled conditions.
  • flumetylsulforim is a compound of Formula I having the following structure:
  • flumetylsulforim includes all forms of the compound of Formula I including, but not limited to, optical isomer, salt, amorphous, crystalline, solvate and hydrate forms.
  • Flumetylsulforim may be prepared, for example, using the processes described in U.S. Patent No. 9,850,215, issued December 26, 2017 and U.S. Patent No. 9,840,476, issued December 12, 2017, the contents of each of which are incorporated herein by reference in their entirety. Flumetylsulforim may also be prepared, for example, using the processes described in PCT International Application Publication No. WO/2021/059160, published April 1, 2021, and PCT International Application Publication No. WO/2021/181274, published September 16, 2021, the contents of each of which are incorporated herein by reference in their entirety.
  • Crystalline forms of the compound of Formula I, and processes of preparation, are disclosed in PCT International Application Publication No. WO 2019/038583 Al, published February 28, 2019, and PCT International Application No. PCT/IB2022/054132, filed May 4, 2022, the entire content of each of which is hereby incorporated by reference.
  • the term “effective” when used in connection with an amount of flumetylsulforim, or a combination, mixture or composition thereof refers to an amount of flumetylsulforim, or combination, mixture or composition thereof that achieves an agriculturally beneficial level of treating a plant or locus against infection by a fungal pathogen when applied to the plant or locus and does not cause any significant damage to the plant or locus.
  • the effective amount is an amount of flumetylsulforim, or combination, mixture or composition thereof that achieves at least 70%, preferably 75%, more preferably 80%. 85%, 90%, 95% or 100% efficacy in treating a plant or locus against infection by the fungal pathogen when applied to the plant or locus and does not cause any significant damage to the plant.
  • fungal pathogen refers to fungal pathogen strains that exist at the time of filing of this application or have existed in the past.
  • fungal pathogen does not include fungal pathogen strains that emerge for the first time after the filing of this application.
  • the term “resistant” when used to describe a fungal pathogen in connection with a fungicide means that the fungicide is less than 80%, preferably less than 75%, more preferably less than 70% effective for treating a plant or locus against infection by the fungal pathogen when applied to the plant or locus at an amount that is commercially recommended for use in treating the plant or locus against infection by the species of fungal pathogen.
  • the commercially recommended amount for a fungicide often specified as application rates of the commercial formulation, may be found on the label accompanying the commercial formulation.
  • the commercially recommended application rates of the commercial formulation may vary depending on factors such as the species of plant and the species of fungal pathogen to be treated.
  • Resistance of a fungal pathogen to a fungicide may develop gradually over time or appear suddenly.
  • Multi-step (or continuous or quantitative) resistance is when a sensitivity shift occurs and the fungal pathogen becomes less sensitive to the fungicide over time resulting in a gradual increase in the amount of fungicide required to be applied to maintain the same adequate level of control. This gradual erosion of fungicide efficacy is normally due to the accumulation of target site mutations and/or the overexpression of the target. For example, multi-step resistance is observed in certain strains of Septoria against tebuconazole.
  • Disruptive (or discrete or qualitative) resistance is when a fungal pathogen can suddenly tolerate high doses of a fungicide such that the amount of fungicide required for adequate control is often impracticable. This type of resistance is due to the development of target site mutation(s) that have catastrophic effects on the binding of the fungicide to its target.
  • the resistance exhibited by the fungal pathogen to the non-flumetylsulforim fungicide(s) may be multi-step resistance or disruptive resistance.
  • treating a plant or locus against infection by a fungal pathogen includes, but is not limited to, protecting the plant or locus against infection by the fungal pathogen and/or controlling infection by the fungal pathogen of the plant or locus.
  • protecting the plant or locus against infection by the fungal pathogen includes, but is not limited to, protecting the plant or locus against fungal attack, protecting the plant or locus from fungal disease, and/or preventing fungal infection of the plant or locus.
  • controlling infection by the fungal pathogen of the plant or locus includes, but is not limited to, controlling fungal disease infecting the plant or locus, controlling a plant or soil disease caused by phytopathologic fungi, controlling fungal attack on the plant or locus, reducing fungal infection of the plant or locus, and/or curing plant or soil disease caused by phytopathologic fungi.
  • the term “protectant application” means an application of fungicide for preventing fungal infection of the plant or locus, wherein the fungicide or combination, mixture or composition thereof is applied before infection occurs, before any disease symptoms are shown or when the disease pressure is low. Disease pressure may be assessed based on the conditions associated with disease development such as spore concentration and certain environmental conditions.
  • the term “curative application” means an application of fungicide for controlling fungal infection of the plant or locus, wherein the fungicide or combination, mixture or composition thereof is applied after an infection or after disease symptoms are shown.
  • 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.
  • Plant includes agricultural crops such as field crops (soybean, maize, wheat, rice, etc.), vegetable crops (potatoes, cabbages, etc.) and fruits (peach, etc.).
  • propagation material is to be understood to denote all the generative parts of the plant such as seeds and spores, seedlings, and vegetative structures such as bulbs, corms, tubers, rhizomes, roots stems, basal shoots, stolons and buds.
  • locus includes not only areas where fungal infection may already be shown, but also areas where fungal infection have yet to show, and also to areas under cultivation. Locus includes, but is not limited to, soil and other plant growth medium.
  • agriculturally acceptable carrier means carriers which are known and accepted in the art for the formation of compositions for agricultural or horticultural use.
  • ha refers to hectare
  • “40 g a.i./ha to 100 g a.i./ha” includes 40 g a.i./ha, 40.1 g a.i./ha, 40.2 g a.i./ha, 40.3 g a.i./ha, 40.4 g a.i./ha, etc. up to 100 g a.i./ha.
  • Flumetylsulforim provides control of a variety of pathogens affecting economically important crops including, but not limited to, ascomycetes and basidiomycetes.
  • flumetylsulforim’ s mode of action is not fully characterized in literature. There is also no disclosure in literature on whether flumetylsulforim’ s mode of action overlaps with the mode of action of known fungicides. This makes it difficult, if not impossible, to predict whether flumetylsulforim will be effective for controlling and/or preventing infection by fungal strains that are resistant to known fungicides.
  • cross-resistance is known to occur even for fungicides having different modes of action. See Yang, L. et al. (2019). Cross-resistance of the pathogenic fungus Alternaria alternata to fungicides with different modes of action. BMC Microbiology, 19(1): 205.
  • flumetylsulforim is effective against fungal strains that are resistant to known fungicides, including, for example, SDHI fungicides, DMI fungicides, and 2,6-dinitroaniline fungicides.
  • flumetylsulforim has consistent and high efficacy across all resistant fungal strains tested, even when flumetylsulforim is applied at lower rates compared to commercially available fungicides.
  • Commercially available fungicides are often more effective against some fungal strains and less effective against others. This variability in efficacy across different fungal strains creates practical challenges for users because choosing the proper fungicide requires an analysis of the fungal strains to be prevented and/or controlled. This increase cost. Overtime, the dominant strain(s) may also change and render the originally selected fungicide inadequate to achieve the desired level of control.
  • the consistent and high efficacy of flumetylsulforim against different fungal strains eliminates these practical challenges for users.
  • the present invention provides a method for treating a plant or locus against infection by a fungal pathogen resistant to at least one non-flumetylsulforim fungicide comprising applying an effective amount of flumetylsulforim to the plant or locus so as to thereby treat the plant or locus against infection by the fungal pathogen, wherein the fungal pathogen is other than Zymoseptoria tritici strain Mg Tri-R6.
  • the non-flumetylsulforim fungicide is a DMI fungicide. In some embodiments, the non-flumetylsulforim fungicides are a DMI fungicide and a SDHI fungicide.
  • the DMI fungicide is ipconazole, tebuconazole, metconazole, fenbuconazole, bromuconazole, tetraconazole, penconazole, difenoconazole, prothioconazole, epoxiconazole, mefentrifluconazole, triticonazole, imazalil, prochloraz, azaconazole, etaconazole, bitertanol, fluquinconazole, flusilazole, cyproconazole, triadimenol, hexaconazole, simeconazole, imibenconazole, diniconazole, pyrisoxazole or any combination thereof.
  • the DMI fungicide is metconazole. In some embodiments, the DMI fungicide is tebuconazole.
  • the SDHI fungicide is 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 or any combination thereof.
  • the SDHI fungicide is penthiopyrad.
  • the non-flumetylsulforim fungicide is a SDHI fungicide.
  • the non-flumetylsulforim fungicide is a 2,6-dinitroaniline fungicide. In some embodiments, the 2,6-dinitroaniline fungicide is fluazinam.
  • the non-flumetylsulforim fungicide is a fungicide selected from the group consisting of SDHI fungicide, DMI fungicide, 2,6-dinitroaniline fungicide, methyl-benzimidazole carbamate (MBC) fungicide, dicarboximide fungicide, phenylamide (PA) fungicide, amine (or morpholine) fungicide, phosphorothiolate fungicide, dithiolane fungicide, carboxamide fungicide, hydroxy-(2-amino-)pyrimidine fungicide, anilinopyrimidine (AP) fungicide, N-phenyl carbamate fungicide, quinone outside inhibitor (Qol) fungicide, phenylpyrrole (PP) fungicide, quinoline fungicide, aromatichydrocarbon (AH) fungicide, heteroaromatic fungicide, melanin biosynthesis inhibitor - reductase (MBI-R) fungicide,
  • the non-flumetylsulforim fungicide is phenylamide (PA) fungicide.
  • the PA fungicide in Metalaxyl and/or Metalaxyl-M is not limited to, Metalaxyl and/or Metalaxyl-M.
  • the non-flumetylsulforim fungicide has an efficacy of less than 80% for treating the plant or locus against infection by the fungal pathogen when applied to the plant or locus at an amount that is commercially recommended for use in treating the plant or locus against infection by the species of fungal pathogen.
  • the non-flumetylsulforim fungicide has an efficacy of less than 75% for treating the plant or locus against infection by the fungal pathogen when applied to the plant or locus at an amount that is commercially recommended for use in treating the plant or locus against infection by the species of fungal pathogen.
  • the non-flumetylsulforim fungicide has an efficacy of less than 70% for treating the plant or locus against infection by the fungal pathogen when applied to the plant or locus at an amount that is commercially recommended for use in treating the plant or locus against infection by the species of fungal pathogen.
  • the non-flumetylsulforim fungicide has an efficacy of less than 65% for treating the plant or locus against infection by the fungal pathogen when applied to the plant or locus at an amount that is commercially recommended for use in treating the plant or locus against infection by the species of fungal pathogen.
  • the non-flumetylsulforim fungicide has an efficacy of less than 60% for treating the plant or locus against infection by the fungal pathogen when applied to the plant or locus at an amount that is commercially recommended for use in treating the plant or locus against infection by the species of fungal pathogen.
  • the non-flumetylsulforim fungicide has an efficacy of less than 55% for treating the plant or locus against infection by the fungal pathogen when applied to the plant or locus at an amount that is commercially recommended for use in treating the plant or locus against infection by the species of fungal pathogen.
  • the non-flumetylsulforim fungicide has an efficacy of less than 50% for treating the plant or locus against infection by the fungal pathogen when applied to the plant or locus at an amount that is commercially recommended for use in treating the plant or locus against infection by the species of fungal pathogen.
  • the non-flumetylsulforim fungicide has an efficacy of less than 45% for treating the plant or locus against infection by the fungal pathogen when applied to the plant or locus at an amount that is commercially recommended for use in treating the plant or locus against infection by the species of fungal pathogen.
  • the non-flumetylsulforim fungicide has an efficacy of less than 40% for treating the plant or locus against infection by the fungal pathogen when applied to the plant or locus at an amount that is commercially recommended for use in treating the plant or locus against infection by the species of fungal pathogen. In some embodiments, the non-flumetylsulforim fungicide has an efficacy of less than 35% for treating the plant or locus against infection by the fungal pathogen when applied to the plant or locus at an amount that is commercially recommended for use in treating the plant or locus against infection by the species of fungal pathogen.
  • the non-flumetylsulforim fungicide has an efficacy of less than 30% for treating the plant or locus against infection by the fungal pathogen when applied to the plant or locus at an amount that is commercially recommended for use in treating the plant or locus against infection by the species of fungal pathogen.
  • the non-flumetylsulforim fungicide has an efficacy of less than 25% for treating the plant or locus against infection by the fungal pathogen when applied to the plant or locus at an amount that is commercially recommended for use in treating the plant or locus against infection by the species of fungal pathogen.
  • the amount of flumetylsulforim has a fungicide efficacy of 70-100% in treating a plant or locus against infection by the fungal pathogen.
  • the amount of flumetylsulforim has a fungicide efficacy of 75-100% in treating a plant or locus against infection by the fungal pathogen.
  • the amount of flumetylsulforim has a fungicide efficacy of 80-100% in treating a plant or locus against infection by the fungal pathogen.
  • the amount of flumetylsulforim has a fungicide efficacy of 85-100% in treating a plant or locus against infection by the fungal pathogen.
  • the amount of flumetylsulforim has a fungicide efficacy of 90-100% in treating a plant or locus against infection by the fungal pathogen.
  • the amount of flumetylsulforim has a fungicide efficacy of 95-100% in treating a plant or locus against infection by the fungal pathogen. In some embodiments, the amount of flumetylsulforim has a fungicide efficacy of 98-100% in treating a plant or locus against infection by the fungal pathogen.
  • Fungicide efficacy maybe calculated using, for example, intensity of infection values or Area Under the Disease Progress Curve (AUDPC) values.
  • AUDPC Area Under the Disease Progress Curve
  • the resistance is target site resistance.
  • the fungal pathogen has at least one mutation conferring resistance to DMI fungicide.
  • the fungal pathogen has at least one CYP51 mutation. In some embodiments, the fungal pathogen has two or more CYP51 mutations. In some embodiments, the fungal pathogen has three CYP51 mutations. In some embodiments, the fungal pathogen has four CYP51 mutations. In some embodiments, the fungal pathogen has five CYP51 mutations. In some embodiments, the fungal pathogen has six CYP51 mutations. In some embodiments, at least one of the CYP51 mutation is in the promoter region. In general, the more mutations a fungal strain has on CYP51, the more insertion sites, and the more resistant the fungal strain is to DMI fungicides.
  • the fungal pathogen is a strain of Zymoseptoria tritici having at least one CYP51 mutation. In some embodiments, the fungal pathogen is a strain of Zymoseptoria tritici having two or more CYP51 mutations. In some embodiments, the fungal pathogen is a strain of Zymoseptoria tritici having three CYP51 mutations. In some embodiments, the fungal pathogen is a strain of Zymoseptoria tritici having four CYP51 mutations. In some embodiments, the fungal pathogen is a strain of Zymoseptoria tritici having five CYP51 mutations.
  • the fungal pathogen is a strain of Zymoseptoria tritici having six CYP51 mutations.
  • the more mutations a fungal strain has on CYP51 the more insertion sites, and the more resistant the fungal strain is to DMI fungicides.
  • the CYP51 mutation is selected from the group consisting of L50S, A379G, I381V, AY459/G460/Y461, S524T, D134G, Y431H, N513K, D134G, V136A, Y461S, 134G, 136A, 381V, 461H, V136C, and any combination thereof or equivalent mutation(s).
  • the fungal pathogen has at least one CYTB mutation.
  • the fungal pathogen is a strain of Zymoseptoria tritici having at least one CYTB mutation.
  • the fungal pathogen has at least one MFS 1 mutation. In some embodiments, at least one MFS1 mutation is in the promoter region.
  • the fungal pathogen is a strain of Zymoseptoria tritici having at least one MFS1 mutation.
  • the fungal pathogen has at least one mutation conferring resistance to SDHI fungicide. In some embodiments, the fungal pathogen has a mutation selected from the group consisting of C-N86S, C-H152R, B-T268I, C-N86T, C-T79N, CN86S, and any combination thereof or equivalent mutation(s).
  • the fungal pathogen is a strain of Zymoseptoria tritici selected from the group consisting of Zt 20, Zt 54, Zt 61, Zt 73, Zt 99, Zt 131, Zt 166, Zt 207, Zt 210, Zt 211, Zt 212, ADA 32, Biot 1, Biot 2, Biot 3, Zt S27, BM 2-3, 95-12F, and any combination thereof.
  • the fungal pathogen is a strain of Zymoseptoria tritici selected from the group consisting of Zt 61, Zt 99, Zt 19-52, Zt 20, Zt 38-02, and any combination thereof.
  • the fungal pathogen is Zymoseptoria tritici strain Zt 61.
  • the fungal pathogen is Zymoseptoria tritici strain Zt 99.
  • the fungal pathogen is Zymoseptoria tritici strain Zt 19-52.
  • the fungal pathogen is Zymoseptoria tritici strain Zt 20.
  • the fungal pathogen is Zymoseptoria tritici strain Zt 38-02.
  • the fungal pathogen has at least one mutation conferring resistance to 2,6- dinitroaniline fungicide.
  • the fungal pathogen is P. infestans strain Dark Green.
  • the fungal pathogen is a strain of Potato late blight, caused by Phytophthora infestans.
  • the fungal pathogen is phenylamide-resistant 13 A2 (Blue 13)
  • the resistance is non-target site resistance.
  • Fungicide non-target site resistance mechanisms refer to the ways in which fungi develop resistance to fungicides through processes that do not involve mutations in the target site of the fungicide. These mechanisms can be diverse and may involve changes in metabolic pathways, efflux pumps, or other cellular processes that reduce the efficacy of the fungicide.
  • fungicide non-target site resistance mechanisms include but are not limited to:
  • Fungi can develop increased expression or activity of efflux pumps that actively remove the fungicide from the cell, reducing its concentration and effectiveness;
  • Metabolic Pathway Bypass Some fungi may develop alternative metabolic pathways to bypass the effects of the fungicide, making them less susceptible to its mode of action;
  • Fungi may produce or upregulate specific enzymes that can degrade or modify the fungicide, rendering it inactive or less harmful to the fungus;
  • the fungicide can be sequestered or compartmentalized within the fungal cell, preventing it from reaching its target site and reducing its efficacy;
  • Some fungi may modify the availability or expression of target sites, making the fungicide less effective at binding to and inhibiting these sites;
  • Metabolic Overdrive Fungi can increase their metabolic activity to process the fungicide more rapidly, minimizing its toxic effects
  • Fungi may develop improved DNA repair mechanisms to counteract the fungicide's genotoxic effects
  • Biofilm Formation In certain fungal species, the development of biofilms can protect them from fungicides by creating a physical barrier; and Changes in Cell Wall Permeability: Fungi may modify their cell walls, making them less permeable to the fungicide and reducing its entry into the cell.
  • the fungal pathogen is a strain resistant to different compounds with different mode of action.
  • the fungal pathogen is selected from Leaf Blotch of Wheat (Mycosphaerella graminicola; anamorph: Septoria tritici), Wheat Brown Rust (Puccinia triticina), Stripe Rust (Puccinia striiformis f. sp.
  • fungal pathogen is selected from the group consisting of Pyricularia oryzae, Rhizoctonia solani, sclerotinia sclerotium, Pseudoperonospora cubensis, Venturia inequalis, Podosphaera leucotricha, Botrytis cinerea, Sphaerotheca fuliginea, Pseudoperonospora cubensis, Alternaria solani, Cercospora beticola, Ramularia beticola, Ramularia areola, Erysiphe betae, Phakopsora pachyrhizi, Microsphaera diffusa, Mycosphaerella areola, Corynespora cassiicola, Colletotrichum dematium, Cercospora kikushi, Plasmopara viticola, Mycosphaerella fijiensis, Phytophthora infestans, Colletotrichum caps
  • the plant is selected from the group consisting of soybean, rice, fruit plants, vegetable plants (such as potatoes), sugar beet, rapeseed, grapevine, table grapes, cotton, corn, cereals (such as wheat and barley), pome fruits, banana and any combination thereof.
  • the crops and fungal pathogens are listed in the following table:
  • the crop is wheat, and the fungal pathogen is Zymoseptoria. In some embodiments, the fungal pathogen is Zymoseptoria tritici.
  • the crop is soybean
  • the fungal pathogen is Phakopsora.
  • the fungal pathogen is Phakopsora pachyrhizi.
  • the crop is rice, and the fungal pathogen is Pyricularia. In some embodiments, the fungal pathogen is Pyricularia oryzae.
  • the crop is Oil Seed Rape
  • the fungal pathogen is Sclerotinia.
  • the fungal pathogen is Sclerotinia sclerotiorum.
  • the crop is corn, and the fungal pathogen is Puccinia. In some embodiments, the fungal pathogen is Puccinia sorghi.
  • the crop is barley, and the fungal pathogen is Puccinia. In some embodiments, the fungal pathogen is Puccinia Hordei.
  • the crop is potato, and the fungal pathogen is Phytophthora. In some embodiments, the fungal pathogen is Phytophthora infestans.
  • the crop is pome fruit
  • the fungal pathogen is Venturia.
  • the fungal pathogen is Venturia inaequalis.
  • the fungal pathogen is Venturia pyrina.
  • the crop is grape, and the fungal pathogen is Plasmopara. In some embodiments, the fungal pathogen is Plasmopara viticola. In some embodiments, the crop is banana, and the fungal pathogen is Pseudocercospora. In some embodiments, the fungal pathogen is Pseudocercospora fijiensis.
  • the fungal pathogen is Blumeria graminis.
  • the fungal pathogen is Rhynchosporium. In a specific embodiment, the fungal pathogen is Rhynchosporium secalis.
  • the fungal pathogen is Erysiphe necator.
  • the present invention provides a method for treating a plant against fungal pathogen infection and/or fungal disease comprising applying an amount of flumetylsulforim to a plant or a locus thereof, wherein the fungal pathogen is selected from Blumeria graminis, Rhynchosporium such as Rhynchosporium secalis, Venturia pyrina, Erysiphe necator and Pseudocercospora fijiensis.
  • the fungal pathogen is Blumeria graminis.
  • the fungal pathogen is Rhynchosporium.
  • the fungal pathogen is Rhynchosporium secalis.
  • the fungal pathogen is Venturia pyrina. In some embodiments, the fungal pathogen is Erysiphe necator. In some embodiments, the fungal pathogen is Venturia pyrina. In some embodiments, the fungal pathogen is Pseudocercospora fijiensis.
  • the flumetylsulforim is applied to the root of the plant.
  • the flumetylsulforim is applied to the foliage of the plant.
  • the flumetylsulforim is applied to the seed.
  • the flumetylsulforim is applied to the seedling.
  • flumetylsulforim is applied as seed treatment at a rate between 0.5-50 g ai/100 kg seeds, preferably between 1-25 g ai/100 kg seeds.
  • flumetylsulforim is applied as seed treatment at a rate of 1 g ai/100 kg seeds, 2.5 g ai/100 kg seeds, 5 g ai/100 kg seeds, 10 g ai/100 kg seeds, or 25 g ai/100 kg seeds. In some embodiments, flumetylsulforim is applied as foliar treatment at a rate between 5 and 1000 g ai/ha.
  • flumetylsulforim is applied as foliar treatment at a rate of 6.25 g ai/ha, 12.5 g ai/ha, 25 g ai/ha, 50 g ai/ha, 75 g ai/ha, 100 g ai/ha, 125 g ai/ha, 150 g ai/ha, 175 g ai/ha, 200 g ai/ha, 225 g ai/ha, 250 g ai/ha, 275 g ai/ha, 300 g ai/ha, 400 g ai/ha, 450 g ai/ha, or 500 g ai/ha.
  • treating a plant or locus against infection by a fungal pathogen is controlling an infection by the fungal pathogen and/or a fungal disease associated with an infection by the fungal pathogen.
  • treating a plant or locus against infection by a fungal pathogen is preventing an infection by the fungal pathogen and/or a fungal disease associated with an infection by the fungal pathogen.
  • treating a plant or locus against infection by a fungal pathogen is protecting the plant or locus from infection by the fungal pathogen and/or a fungal disease associated with an infection by the fungal pathogen.
  • the flumetylsulforim is applied by contacting the plant or locus with an effective amount of flumetylsulforim.
  • Application may be made by the use of conventional ground sprayers, granule applicators, and by other conventional means known to those skilled in the art.
  • the flumetylsulforim is applied to root of the plant. In some embodiments, the flumetylsulforim is applied to foliage of the plant. In some embodiments, the plant is a seed or seedling. In some embodiments, the flumetylsulforim is applied to seed. In some embodiments, the flumetylsulforim is applied to seedling.
  • the flumetylsulforim is applied at an amount between 1 g/ha to 1000 g/ha. In some embodiments, the flumetylsulforim is applied at an amount between 1 g/ha to 500 g/ha. In some embodiments, the flumetylsulforim is applied at an amount between 5 g/ha to 1000 g/ha. In some embodiments, the flumetylsulforim is applied at an amount between 5 g/ha to 400 g/ha. In some embodiments, the flumetylsulforim is applied at an amount between 5 g/ha and 250 g/ha. In some embodiments, the flumetylsulforim is applied at an amount between 5 g/ha and 150 g/ha.
  • the flumetylsulforim is applied at an amount between 10 g/ha to 300 g/ha. In some embodiments, the flumetylsulforim is applied at an amount between 25 g/ha and 100 g/ha. In some embodiments, the flumetylsulforim is applied at an amount between 25 g/ha and 150 g/ha. In some embodiments, the flumetylsulforim is applied at an amount between 30 g/ha and 200 g/ha. In some embodiments, the flumetylsulforim is applied at an amount between 40 g/ha and 100 g/ha. In some embodiments, the flumetylsulforim is applied at an amount between 50 g/ha and 200 g/ha.
  • the flumetylsulforim is applied at an amount between 50 g/ha and 100 g/ha. In some embodiments, the flumetylsulforim is applied at an amount between 75 g/ha and 100 g/ha. In some embodiments, the flumetylsulforim is applied at an amount between 100 g/ha and 200 g/ha. In some embodiments, the flumetylsulforim is applied at an amount between 5 g/ha to 120 g/ha. In some embodiments, the flumetylsulforim is applied at an amount between 1 g/ha to 100 g/ha. In some embodiments, the flumetylsulforim is applied at an amount between 1 g/ha to 75 g/ha.
  • the flumetylsulforim is applied at an amount between 1 g/ha to 50 g/ha. In some embodiments, the flumetylsulforim is applied at an amount between 1 g/ha to 25 g/ha. In some embodiments, the flumetylsulforim is applied at an amount between 1 g/ha to 15 g/ha. In some embodiments, the flumetylsulforim is applied at an amount between 2 g/ha to 13 g/ha. In some embodiments, the flumetylsulforim is applied at an amount between 5 g/ha to 10 g/ha.
  • the flumetylsulforim is applied at an amount of about 1 g/ha. In some embodiments, the flumetylsulforim is applied at an amount of about 5 g/ha. In some embodiments, the flumetylsulforim is applied at an amount of about 6.25 g/ha. In some embodiments, the flumetylsulforim is applied at an amount of about 10 g/ha. In some embodiments, the flumetylsulforim is applied at an amount of about 12.5 g/ha. In some embodiments, the flumetylsulforim is applied at an amount of about 20 g/ha. In some embodiments, the flumetylsulforim is applied at an amount of about 25 g/ha.
  • the flumetylsulforim is applied at an amount of about 40 g/ha. In some embodiments, the flumetylsulforim is applied at an amount of about 50 g/ha. In some embodiments, the flumetylsulforim is applied at an amount of about 75 g/ha. In some embodiments, the flumetylsulforim is applied at an amount of about 100 g/ha. In some embodiments, the flumetylsulforim is applied at an amount of about 125 g/ha. In some embodiments, the flumetylsulforim is applied at an amount of about 150 g/ha. In some embodiments, the flumetylsulforim is applied at an amount of about 175 g/ha.
  • the flumetylsulforim is applied at an amount of about 200 g/ha. In some embodiments, the flumetylsulforim is applied at an amount of about 225 g/ha. In some embodiments, the flumetylsulforim is applied at an amount of about 250 g/ha. In some embodiments, the flumetylsulforim is applied at an amount of about 275 g/ha. In some embodiments, the flumetylsulforim is applied at an amount of about 300 g/ha. In some embodiments, the flumetylsulforim is applied at an amount of about 400 g/ha. In some embodiments, the flumetylsulforim is applied at an amount of about 450 g/ha. In some embodiments, the flumetylsulforim is applied at an amount of about 500 g/ha.
  • the flumetylsulforim is applied at an amount of 150 g/ha or less. In some embodiments, the flumetylsulforim is applied at an amount of 100 g/ha or less. In some embodiments, the flumetylsulforim is applied at an amount of 100 g/ha or less, applied twice with a 7-day interval in between applications.
  • the flumetylsulforim is applied at an amount from about 0.5 to about 500 g/100 kg seed. In some embodiments, the flumetylsulforim is applied at an amount of about 3.7 g/100 kg seed. In some embodiments, the flumetylsulforim is applied at an amount of about 11 g/100 kg seed. In some embodiments, the flumetylsulforim is applied at an amount of about 33.3 g/100 kg seed. In some embodiments, the flumetylsulforim is applied at an amount of about 100 g/100 kg seed. In some embodiments, the flumetylsulforim is applied at an amount of about 300 g/100 kg seed.
  • the application rate of flumetylsulforim for controlling Sclerotinia sclerotium as a foliar application in rapeseed is between 75-200 g ai/ha. In some embodiments, the application rate of flumetylsulforim for controlling Sclerotinia sclerotium in soybean as seed treatment is between 1-25 g ai/100 kg seeds.
  • the application rate of flumetylsulforim for controlling Rhizoctonia solani in soybean as seed treatment is between 1-25 g ai/100 kg seeds.
  • the application rate of flumetylsulforim for controlling Phytium ultimum in soybean as seed treatment is between 5-25 g ai/100 kg seeds.
  • the application rate of flumetylsulforim for controlling Fusarium graminearum in soybean as seed treatment is between 5-25 g ai/100 kg seeds.
  • the application rate of flumetylsulforim for controlling Rhizoctonia solani (sheath blight) in rice as a foliar application is between 50-200 g ai/ha.
  • the application rate of flumetylsulforim for controlling Pyricularia oryzae (blast) in rice as a foliar application is between 50-200 g ai/ha.
  • the application rate of flumetylsulforim for controlling Venturia inaequalis (apple scab) in fruits like apple as a foliar application is between 75-200 g ai/ha.
  • the application rate of flumetylsulforim for controlling Podosphaera leucotricha (powdery mildew) in fruits like apple as a foliar application is between 75-200 g ai/ha.
  • the application rate of flumetylsulforim for controlling Botrytis cinerea in strawberry as a foliar application is between 150-500 g ai/ha.
  • the application rate of flumetylsulforim for controlling Sphaerotheca fuliginea (powdery mildew) in zucchini as a foliar application is between 75-200 g ai/ha.
  • the application rate of flumetylsulforim for controlling Pseudoperonospora cubensis (downy mildew) in cucumber as a foliar application is between 75-200 g ai/ha.
  • the application rate of flumetylsulforim for controlling Alternaria solani (early blight) in potato as a foliar application is between 75-200 g ai/ha. In some embodiments, the application rate of flumetylsulforim for controlling Alternaria solani in potato as a foliar application is between 175 g ai/ha to 200 g ai/ha.
  • the application rate of flumetylsulforim for controlling Cercospora beticola in sugar beet as a foliar application is between 50-150 g ai/ha.
  • the application rate of flumetylsulforim for controlling Cercospora beticola in sugar beet as a foliar application is about 125 g ai/ha.
  • the application rate of flumetylsulforim for controlling Ramularia beticola in sugar beet as a foliar application is between 50-150 g ai/ha.
  • the application rate of flumetylsulforim for controlling Erysiphe betae (powdery mildew) in sugar beet as a foliar application is between 50-150 g ai/ha.
  • the application rate of flumetylsulforim for controlling Phakopsora pachyrhizi (Asian soybean rust) in soybean as a foliar application is between 50-200 g ai/ha.
  • the application rate of flumetylsulforim for controlling Microsphaera diffusa (powdery mildew) in soybean as a foliar application is between 50-200 g ai/ha.
  • the application rate of flumetylsulforim for controlling Cercospora kikushi in soybean as a foliar application is between 50-200 g ai/ha.
  • the application rate of flumetylsulforim for controlling Corynespora cassiicola in soybean as a foliar application is between 50-200 g ai/ha.
  • the application rate of flumetylsulforim for controlling Colletotrichum dematium in soybean as a foliar application is between 50-200 g ai/ha.
  • the application rate of flumetylsulforim for controlling Mycosphaerella areola in cotton as a foliar application is between 50-200 g ai/ha.
  • the application rate of flumetylsulforim for controlling Ramularia areola in cotton as a foliar application is between 50-200 g ai/ha. In some embodiments, the application rate of flumetylsulforim for controlling Colletotrichum dematium (anthracnose) in chili as a foliar application is between 50-200 g ai/ha.
  • the application rate of flumetylsulforim for controlling Plasmopara viticola (downy mildew) in grapevine as a foliar application is between 50-200 g ai/ha.
  • the application rate of flumetylsulforim for controlling Mycosphaerella fijiensis (black sigatoka) in banana as a foliar application is between 50-200 g ai/ha.
  • the application rate of flumetylsulforim for controlling Phytophtora infestans in potato as a foliar application is between 100 g ai/ha to 200 g ai/ha.
  • the application rate of flumetylsulforim for controlling Colletotrichum capsici in chili as a foliar application is between 150-250 g ai/ha.
  • the application rate of flumetylsulforim for controlling Podosphaera fuliginea (powdery mildew) in zucchini as a foliar application is between 100-200 g ai/ha.
  • the method when the fungal pathogen is resistant to a fungicide having a mode of action, the method is more effective for treating the plant or locus against infection by the fungal pathogen compared to application of a fungicide having a different mode of action than the fungicide to which the fungal pathogen is resistant to at the same amount or an amount that is commercially recommended for use in treating the plant or locus against infection by the species of fungal pathogen.
  • the method when the fungal pathogen is resistant to a fungicide having a mode of action, is at least 30%, at least 40%, at least 50%, at least 60%, at least 70%, at least 80%, at least 90%, at least 100%, at least 150%, at least 200%, at least 250% or at least 300% more effective for treating the plant or locus against infection by the fungal pathogen compared to application of a fungicide having a different mode of action than the fungicide to which the fungal pathogen is resistant to at the same amount or an amount that is commercially recommended for use in treating the plant or locus against infection by the species of fungal pathogen.
  • the method when the fungal pathogen is resistant to a fungicide having a mode of action, the method achieves the same efficacy as a fungicide having a different mode of action than the fungicide to which the fungal pathogen is resistant to for treating the plant or locus against infection by the fungal pathogen at an amount that is (i) substantially less than the amount of the fungicide having a different mode of action than the fungicide to which the fungal pathogen is resistant to or (ii) substantially less than the amount of the fungicide having a different mode of action than the fungicide to which the fungal pathogen is resistant to that is commercially recommended for use in treating the plant or locus against infection by the species of fungal pathogen.
  • the method when the fungal pathogen is resistant to DMI fungicide, the method is more effective for treating the plant or locus against infection by the fungal pathogen compared to application of another non-DMI fungicide at the same amount or an amount that is commercially recommended for use in treating the plant or locus against infection by the species of fungal pathogen.
  • the method when the fungal pathogen is resistant to DMI fungicide, the method is at least 30%, at least 40%, at least 50%, at least 60%, at least 70%, at least 80%, at least 90%, at least 100%, at least 150%, at least 200%, at least 250% or at least 300% more effective for treating the plant or locus against infection by the fungal pathogen compared to application of another non- DMI fungicide at the same amount or an amount that is commercially recommended for use in treating the plant or locus against infection by the species of fungal pathogen.
  • the method when the fungal pathogen is resistant to DMI fungicide, the method achieves the same efficacy as another non-DMI fungicide for treating the plant or locus against infection by the fungal pathogen at an amount that is (i) substantially less than the amount of the other non-DMI fungicide or (ii) substantially less than the amount of the non-DMI fungicide that is commercially recommended for use in treating the plant or locus against infection by the species of fungal pathogen.
  • the non-DMI fungicide is penthiopyrad.
  • the method is more effective for treating the plant or locus against infection by the fungal pathogen compared to application of another non-SDHI and non-DMI fungicide at the same amount or an amount that is commercially recommended for use in treating the plant or locus against infection by the species of fungal pathogen.
  • the method is at least 30%, at least 40%, at least 50%, at least 60%, at least 70%, at least 80%, at least 90%, at least 100%, at least 150%, at least 200%, at least 250% or at least 300% more effective for treating the plant or locus against infection by the fungal pathogen compared to application of another non-SDHI and non-DMI fungicide at the same amount or an amount that is commercially recommended for use in treating the plant or locus against infection by the species of fungal pathogen.
  • the method achieves the same efficacy as another non-SDHI and non-DMI fungicide for treating the plant or locus against infection by the fungal pathogen at an amount that is (i) substantially less than the amount of the other non-SDHI and non-DMI fungicide or (ii) substantially less than the amount of the non-DMI and non-SDHI fungicide that is commercially recommended for use in treating the plant or locus against infection by the species of fungal pathogen.
  • the method when the fungal pathogen is resistant to SDHI fungicide, the method is more effective for treating the plant or locus against infection by the fungal pathogen compared to application of another non-SDHI fungicide at the same amount or an amount that is commercially recommended for use in treating the plant or locus against infection by the species of fungal pathogen.
  • the method when the fungal pathogen is resistant to SDHI fungicide, the method is at least 30%, at least 40%, at least 50%, at least 60%, at least 70%, at least 80%, at least 90%, at least 100%, at least 150%, at least 200%, at least 250% or at least 300% more effective for treating the plant or locus against infection by the fungal pathogen compared to application of another non- SDHI fungicide at the same amount or an amount that is commercially recommended for use in treating the plant or locus against infection by the species of fungal pathogen.
  • the method when the fungal pathogen is resistant to SDHI fungicide, the method achieves the same efficacy as another non-SDHI fungicide for treating the plant or locus against infection by the fungal pathogen at an amount that is (i) substantially less than the amount of the other non-SDHI fungicide or (ii) substantially less than the amount of the non-SDHI fungicide that is commercially recommended for use in treating the plant or locus against infection by the species of fungal pathogen..
  • the non-SDHI fungicide is metconazole. In some embodiments, the non- SDHI fungicide is tebuconazole.
  • the method when the fungal pathogen is resistant to a 2,6-dinitroaniline fungicide, the method is more effective for treating the plant or locus against infection by the fungal pathogen compared to application of another non-2,6-dinitroaniline fungicide at the same amount or an amount that is commercially recommended for use in treating the plant or locus against infection by the species of fungal pathogen.
  • the method is at least 30%, at least 40%, at least 50%, at least 60%, at least 70%, at least 80%, at least 90%, at least 100%, at least 150%, at least 200%, at least 250% or at least 300% more effective for treating the plant or locus against infection by the fungal pathogen compared to application of another non-2,6-dinitroaniline fungicide at the same amount or an amount that is commercially recommended for use in treating the plant or locus against infection by the species of fungal pathogen.
  • the method when the fungal pathogen is resistant to a 2,6-dinitroaniline fungicide, the method achieves the same efficacy as another non-2,6-dinitroaniline fungicide for treating the plant or locus against infection by the fungal pathogen at an amount that is (i) substantially less than the amount of the other non-2,6-dinitroaniline fungicide or (ii) substantially less than the amount of the non-2,6-dinitroaniline fungicide that is commercially recommended for use in treating the plant or locus against infection by the species of fungal pathogen..
  • the method comprises application of at least one additional pesticide.
  • the pesticide is a fungicide, herbicide, insecticide, acaricides, or nematicide.
  • the present invention also provides a composition comprising flumetylsulforim and an agriculturally acceptable carrier for use in treating a plant or locus against infection by a fungal pathogen resistant to at least one non-flumetylsulforim fungicide , wherein the fungal pathogen is other than Zymoseptoria tritici strain Mg Tri-R6.
  • the present invention also provides use of a composition comprising flumetylsulforim and an agriculturally acceptable carrier for treating a plant or locus against infection by a fungal pathogen resistant to at least one non-flumetylsulforim fungicide , wherein the fungal pathogen is other than Zymoseptoria tritici strain Mg Tri-R6.
  • the present invention also provides use of flumetylsulforim in the manufacturing of a composition for treating a plant or locus against infection by a fungal pathogen resistant to at least one non- flumetylsulforim fungicide, wherein the fungal pathogen is other than Zymoseptoria tritici strain Mg Tri-R6.
  • Composition comprising flumetylsulforim may be formulated in accordance with any one or any combination of the features disclosed in PCT International Application Publication Nos. WO/2020/095181, published May 14, 2020, and WO/2021/224802, published November 11, 2021, the entire content of each of which is hereby incorporated by reference.
  • the composition comprises a liquid carrier, wherein the solubility of the compound of Formula I in the liquid carrier is less than 5000 ppm.
  • the composition comprises at least one stabilizing surfactant.
  • the pH of the composition is in the range of 5 to 7.5. In some embodiments, the composition has a water content of less than 0.5% by weight based on the total weight of the composition.
  • the composition has a viscosity of at least 500 cP.
  • the composition comprises at least one adjuvant.
  • the adjuvant is selected from the group consisting of:
  • the composition comprises (a) a fungicidally effective and substantially pure amount of flumetylsulforim or a fungicidally effective amount of a mixture containing flumetylsulforim, wherein 95% or more by weight of the mixture is flumetylsulforim, and (b) a liquid carrier.
  • 95% or more of the amount of flumetylsulforim is in the form of Form I polymorph, Form II polymorph, Hydrate, or a mixture thereof.
  • Form I polymorph, Form II polymorph, and Hydrate of flumetylsulforim are described below.
  • the present invention also provides a method for treating a seed or seedling against infection by a fungal pathogen resistant to at least one non-flumetylsulforim fungicide comprising applying flumetylsulforim to the seed, seedling and/or a locus thereof so as to thereby treat the seed or seedling against infection by the fungal pathogen.
  • the composition comprises at least one additional pesticide.
  • the pesticide is a fungicide, herbicide, insecticide, acaricides, or nematicide.
  • the present invention also provides a method of producing a plant resistant to infection by a fungal pathogen resistant to at least one non-flumetylsulforim fungicide, the method comprising applying flumetylsulforim to the plant, a seed of the plant, a seedling of the plant, or a locus thereof so as to thereby produce a plant resistant to infection by the fungal pathogen.
  • the present invention also provides a plant resistant to infection by a fungal pathogen resistant to at least one non-flumetylsulforim fungicide, wherein the seed adapted to produce the plant, the seedling adapted to produce the plant, or a locus of plant is treated with flumetylsulforim.
  • the present invention also provides a plant seed or seedling adapted to produce a plant resistant to infection by a fungal pathogen resistant to at least one non-flumetylsulforim fungicide, wherein the plant seed or seedling is treated with flumetylsulforim.
  • the present invention also provides a mature plant resistant to infection by a fungal pathogen resistant to at least one non-flumetylsulforim fungicide, wherein the mature plant or a seed or seedling adapted to produce the mature plant is treated with an amount of flumetylsulforim, and wherein the treated mature plant has an ecologically acceptable effect on non-target organisms that contact the treated mature plant.
  • Flumetylsulforim includes all forms of the compound of Formula I:
  • optical isomer including, but not limited to, optical isomer, salt, amorphous, crystalline, solvate and hydrate forms.
  • Crystalline Forms I, II, Hydrate, S5, S8 and SI are defined in PCT International Application Publication No. WO 2019/038583 Al, published February 28, 2019, the entire content of which is hereby incorporated by reference.
  • Forms I, II, Hydrate, S5, S8 and SI exhibit distinct spectral characteristics as depicted by their X-ray diffraction patterns.
  • the crystalline form is Form I.
  • the powder X-ray diffraction pattern of Form I exhibits characteristic peaks at 2-theta angles of 9.08, 10.98, 14.05, 17.51, 18.75, 21.63, 23.33, 24.70, 24.83, 25.37, 26.51 and 29.23.
  • the powder X-ray diffraction pattern of Form I comprises characteristic peaks at 2-theta angles of 14.05, 17.51, 18.75, 21.63 and 26.51.
  • the powder X-ray diffraction pattern of Form I comprises characteristic peaks at 2-theta angles of 14.05, 17.51, 18.75 and 21.63.
  • the crystalline form is Form II.
  • the powder X-ray diffraction pattern of Form II exhibits characteristic peaks at 2-theta angles of 7.98, 9.20, 9.96, 11.88, 15.99, 18.49, 21.23, 22.33, 22.59, 26.73.
  • the powder X-ray diffraction pattern of Form II comprises characteristic peaks at 2-theta angles of 9.20, 9.96, 11.88, 22.33 and 22.59.
  • the powder X-ray diffraction pattern of Form II comprises characteristic peaks at 2-theta angles of 9.20, 11.88, 22.33 and 22.59.
  • the crystalline form is Form Hydrate.
  • the powder X-ray diffraction pattern of Form Hydrate exhibits characteristic peaks at 2-theta 5.34, 7.48, 10.68, 16.05, 21.79, 22.99, 23.19, 24.95, 26.95, 27.63.
  • the powder X-ray diffraction pattern of Form Hydrate comprises characteristic peaks at 2-theta angles of 5.34, 7.48, 10.68, 16.05 and 21.79.
  • the powder X-ray diffraction pattern of Form Hydrate comprises characteristic peaks at 2-theta angles of 5.34, 7.48, 10.68 and 16.05.
  • the crystalline form is Form S5.
  • the powder X-ray diffraction pattern of Form S5 exhibits characteristic peaks at 2-theta 5.42, 7.50, 10.06, 10.82, 12.80, 16.91, 21.55, 23.13, 24.83, 26.81, 27.77.
  • the powder X-ray diffraction pattern of Form S5 comprises characteristic peaks at 2-theta angles of 5.42, 7.50, 10.06, 10.82, and 16.91.
  • the powder X-ray diffraction pattern of Form S5 comprises characteristic peaks at 2-theta angles of 5.42, 7.50, 10.82 and 16.91.
  • the crystalline form is Form S8.
  • the powder X-ray diffraction pattern of Form S8 exhibits characteristic peaks at 2-theta 4.7, 5.00, 5.38, 6.26, 9.66, 15.93, 21.05, 23.97, 24.69. In one embodiment, the powder X-ray diffraction pattern of Form S8 comprises characteristic peaks at 2-theta angles of 4.7, 5.00, 5.38, 6.26, 9.66 and 23.97. In one embodiment, the powder X-ray diffraction pattern of Form S8 comprises characteristic peaks at 2- theta angles of 4.7, 5.00, 9.66 and 23.97.
  • the crystalline form is Form SI.
  • the powder X-ray diffraction pattern of Form SI exhibits characteristic peaks at 2-theta 5.34, 7.48, 10.10, 10.68, 12.90, 16.07, 21.83, 23.09, 24.91, 26.93.
  • the powder X-ray diffraction pattern of Form SI comprises characteristic peaks at 2-theta angles of 5.34, 7.48, and 10.68.
  • the powder X-ray diffraction pattern of Form SI comprises characteristic peaks at 2- theta angles of 5.34, 7.48, 10.68 and 21.83.
  • the powder X-ray diffraction pattern of Form SI comprises characteristic peaks at 2-theta angles of 5.34, 7.48, 10.68, 16.07 and 21.83.
  • Crystalline Forms III, Illa, 01 and 02 are defined in PCT International Application No. PCT/IB2022/054132. Forms III, Illa, 01 and 02 exhibit distinct spectral characteristics as depicted by their X-ray diffraction patterns.
  • the crystalline form is Form III.
  • the powder X-ray diffraction pattern of Form III exhibits characteristic peaks at 4.5, 5.1, 9.1, 10.1, 22.4, 23.5 ⁇ - 0.2 deg 2-theta.
  • the X-ray powder diffraction pattern of Form III comprises characteristic peaks at 4.5, 5.1, 9.1, 10.1, 11.9, 14.2, 16.1, 22.4, 23.5 ⁇ 0.2 deg 2-theta.
  • the crystalline form is Form Illa.
  • the powder X-ray diffraction pattern of Form Illa exhibits characteristic peaks at 4.5, 5.0, 9.3, 10.0, 22.3, 22.6 ⁇ 0.2 deg 2-theta.
  • the X-ray powder diffraction pattern of Form Illa comprises characteristic peaks at 4.5, 5.0, 9.3, 10.0, 11.9, 14.2, 16.0, 22.3, 22.6, 25.3 ⁇ 0.2 deg 2-theta.
  • the crystalline form is Form 01.
  • the powder X-ray diffraction pattern of Form 01 exhibits characteristic peaks at 5.1, 6.4, 7.5, 10.3, 16.1 ⁇ 0.2 deg 2- theta.
  • the X-ray powder diffraction pattern of Form 01 comprises characteristic peaks at 5.1, 6.4, 7.5, 10.3, 12.2, 13.4, 14.9, 16.1, 18.4 ⁇ 0.2 deg 2-theta.
  • the crystalline form is Form 02.
  • the powder X-ray diffraction pattern of Form 02 exhibits characteristic peaks at 7.5, 14.3, 15.8, 22.4, 24.7 ⁇ 0.2 deg 2-theta.
  • the X-ray powder diffraction pattern of Form 02 comprises characteristic peaks at 7.5, 11.9, 14.3, 15.8, 18.7, 22.4, 24.7, 27.4, 31.1 ⁇ 0.2 deg 2-theta.
  • Flumetylsulforim may refer to any one or any mixture of the forms of the compound of Formula I described above.
  • the composition may comprise at least one adjuvant selected from the group consisting of:
  • the composition is formulated for dilution in water before application.
  • the composition is a concentrated formulation which can be dispersed in water, or another liquid, for application.
  • the composition is dust-like or granular, which can then be applied without further treatment.
  • the compositions disclosed herein can be prepared according to procedures which are conventional in the agricultural chemical art.
  • compositions 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 disclosure contemplates all vehicles by which flumetylsulforim can be formulated for delivery and used as fungicide.
  • pots were transferred in a climatic chamber: temperature of 20°C day/17°C night - photoperiod of 16 h light/8 h dark and controlled relative humidity.
  • the fungicide efficacies were determined from the Area Under the Disease Progress Curve (AUDPC) values and expressed as a percentage of the untreated control.
  • the AUDPC is a quantitative measure of disease intensity over time.
  • the most commonly used method for estimating the AUDPC, the trapezoidal method is performed by multiplying the average disease intensity between each pair of adjacent timepoints by the corresponding time interval and this for each time interval.
  • Z. tritici strain Zt StA control strain
  • the intensity of infection by Z. tritici strain Zt StA of the second leaf blade of wheat plants cv. ALIXAN untreated or treated preventively with ADF-16, penthiopyrad, metconazole or tebuconazole, at 2 rates each, in controlled conditions is shown in Table 3 and Figure 1.
  • the AUDPC of Z. tritici strain Zt StA on wheat plants cv. ALIXAN untreated or treated preventively with ADF-16, penthiopyrad, metconazole or tebuconazole, at 2 rates each, in controlled conditions, is shown in Table 4 and Figure 2.
  • the AUDPC of Z. tritici strain Zt 61 on wheat plants cv. ALIXAN untreated or treated preventively with ADF-16, penthiopyrad, metconazole or tebuconazole, at 2 rates each, in controlled conditions, is shown in Table 6 and Figure 5.
  • Z. tritici strain Zt 61 has multi-step resistance to DMI and SDHI fungicides where higher application rates of penthiopyrad, metconazole or tebuconazole have moderate fungicide efficacy of 85% or greater but at the lower application rates, fungicide efficacy of 70% or less was observed and is no longer sufficient.
  • the AUDPC of Z. tritici strain Zt 99 on wheat plants cv. ALIXAN untreated or treated preventively with ADF-16, penthiopyrad, metconazole or tebuconazole, at 2 rates each, in controlled conditions, is shown in Table 8 and Figure 8.
  • Z. tritici strain Zt 19-52 The intensity of infection by Z. tritici strain Zt 19-52 of the second leaf blade of wheat plants cv. ALIXAN untreated or treated preventively with ADF-16, penthiopyrad, metconazole or tebuconazole, at 2 rates each, in controlled conditions, is shown in Table 9 and Figure 10.
  • a comparison of the fungicide efficacy, obtained from the AUDPC values of ADF-16, penthiopyrad, metconazole or tebuconazole, at 2 rates each, applied 24 hours before the inoculation of wheat plants cv. ALIXAN with pycnospores of Zymoseptoria tritici strain Zt 38-02 in controlled conditions is shown in Figure 16.
  • the aim of the second step consists of determining the in planta susceptibility patterns of all the 8 selected Z. tritici strains towards the 5 retained fungicide molecules.
  • Potato plantlets (var. Bintje) were grown for 7 weeks in a 7*7*7 cm pots (15 leaves stage). The leaves were cut and treated with a fungicide preparation based on ADF-16 50 EC at the rate of 125ga.i./ha (416.7 ppm) or Fluazinam 500 SC at the rate of 125ga.i./ha (416.7 ppm) prepared in a volume of water corresponding to 300 L/ha or with distilled water (Control). Four leaflets were treated for each condition tested.
  • Disease assessments were carried out from 3 to 12 days post inoculation (dpi) by evaluating the percentage of disease symptoms, corresponding to the surface of potato leaflets with symptomatic disease (late blight symptoms).
  • the Area Under the Disease Progress Curve is a quantitative measure of disease intensity over time.
  • the most commonly used method for estimating the AUDPC the trapezoidal method, is performed by multiplying the average disease intensity between each pair of adjacent time points by the time interval corresponding, and this for each time interval.
  • the efficacy of each tested formulation was determined from the AUDPC value and expressed as a percentage of the untreated control (water).

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Abstract

La présente invention concerne un procédé de traitement d'une plante ou d'un locus contre une infection par un pathogène fongique résistant à au moins un fongicide non flumétylsulforim comprenant l'application d'une quantité efficace de flumétylsulforim à la plante ou au locus de façon à traiter la plante ou le locus contre une infection par le pathogène fongique, le pathogène fongique étant autre que la souche de Zymoseptoria tritici Mg Tri-R6.
PCT/IB2023/057879 2022-08-03 2023-08-03 5-fluoro-4-imino-3-méthyl-1-tosyl-3,4-dihydropyrimidin-2 (1h)-one pour champignon résistant aux fongicides Ceased WO2024028812A1 (fr)

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AU2023318916A AU2023318916A1 (en) 2022-08-03 2023-08-03 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidin-2(1h)-one for fungicide-resistant fungus
CA3263912A CA3263912A1 (fr) 2022-08-03 2023-08-03 5-fluoro-4-imino-3-méthyl-1-tosyl-3,4-dihydropyrimidin-2 (1h)-one pour champignon résistant aux fongicides

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