Fungicidal mixtures and composition comprising thereof

Fungicidal mixtures with a compound of Formula I and co-fungicides address health and resistance issues by enhancing efficacy against fungal pathogens through multiple-site action, offering safer and more effective disease control.

WO2025248515A1PCT designated stage Publication Date: 2025-12-04ADAMA MAKHTESHIM LTD
View PDF 3 Cites 0 Cited by

Patent Information

Application Number
PCT/IL2025/050443
Authority / Receiving Office
WO · WO
Patent Type
Applications
Current Assignee / Owner
Priority Date
2024-05-26
Filing Date
2025-05-25
Publication Date
2025-12-04

AI Technical Summary

Technical Problem

The intensive use of fungicides in agriculture leads to health risks and the development of resistance, necessitating the need for safer, more effective, and less dosage-dependent fungicidal solutions.

Method used

Development of fungicidal mixtures comprising a compound of Formula I and at least one co-fungicide, including multisite contact fungicides, quinone inhibitors, succinate dehydrogenase inhibitors, and other fungicides, which act on multiple sites to enhance efficacy against fungal pathogens like Ascomycetes and wheat leaf blotch.

Benefits of technology

The mixtures provide improved efficacy against fungal diseases, reducing the amount of fungicides required and minimizing resistance development, while being safer for use.

✦ Generated by Eureka AI based on patent content.

Smart Images

  • Figure IMGF000003_0001
    Figure IMGF000003_0001
  • Figure IMGF000018_0001
    Figure IMGF000018_0001
  • Figure IMGF000017_0001
    Figure IMGF000017_0001
Patent Text Reader

Abstract

The invention concerns fungicidal mixtures and compositions comprising (a) a compound of Formula I being 5-fluoro-4-imino-3- methyl-3,4-dihydropyrimidin-2(lH)-one and (b) at least one co¬ fungicide, especially pyridaclometyl. Uses and methods of treating a plant or locus thereof in order to control or prevent fungal infection.
Need to check novelty before this filing date? Find Prior Art

Description

FUNGICIDAL MIXTURES AND COMPOSITION COMPRISING THEREOFField of the Invention

[0001] This invention concerns fungicidal mixtures and compositions comprising (a) a compound of Formula I and (b) at least one co- fungicide and uses thereof.Background of the Invention

[0002] Fungicides are compounds of natural or synthetic origin which act to protect plants against damage caused by fungi. Despite the benefits derived from the use of fungicides in agriculture such as protection of crops and improved productivity, it is nowadays desirable to reduce the amount of fungicides used in the fields owing to the potential health risks associated with an intensive use of agrochemicals.

[0003] Furthermore, repeated usage of a single fungicide frequently leads to the development of resistance to the related fungicides. Consequently, research is being conducted to produce fungicides and combinations of fungicides that are safer, that have better performance, that are effective over long periods of time, that require lower dosages, that are easier to use, and that cost less.

[0004] It is an object of this disclosure to provide mixtures comprising the compound of Formula I and at least one co-fungicide that are effective and safe. It is a further object of this disclosure to provide composition comprising these mixtures and uses thereof and method for treating a plant or locus against fungal infection.Summary of the Invention

[0005] It is an object of this invention to provide mixtures and compositions comprising fungicidal compounds. The mixtures and compositions are capable of preventing or curing, or both, diseases caused by fungi, such as of the class Ascomycetes. In addition, the mixture and compositions have improved efficacy against pathogens, such as leaf blotch of wheat. In accordance with this invention, mixture and compositions are provided along with use thereof and methods for their use.Detailed Description of the Invention

[0006] The present invention concerns fungicidal mixture comprising a fungicidally effective amount of (a) a compound of Formula I and (b) at least one co-fungicide.Formula I

[0007] in some embodiments, the co-fungicide is selected from a group consisting of multisite contact fungicide, Qi I fungicide (quinone inside inhibitors), Qol fungicide (quinone outside inhibitors) QoSI fungicide (quinone outside stigmateliin 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 / or benthiavalicarb-isopropyl.

[0008] In some embodiments, the co-fungicide is multi-site contact fungicide. In some embodiments, the co-fungicide is Qil fungicide (quinone inside inhibitors). In some embodiments, the co-fungicide is Qol fungicide (quinone outside inhibitors). In some embodiments, the co-fungicide is QoSI fungicide (quinone outside stigmateliin subsite inhibitors). In some embodiments, the co-fungicide is SDHI fungicide (succinate dehydrogenase inhibitors). In some embodiments, the co-fungicide is a demethylation inhibitor fungicide (DMI fungicide). In some embodiments, the co-fungicide is phenyl amide fungicide. In some embodiments, the co-fungicide is methyl-benzimidazole-carbamate (MBC) fungicide. In some embodiments, the co-fungicide is carboxylic acid amide fungicide. In some embodiments, the co-fungicide is benzamide fungicide. In some embodiments, the co- fungicide is natural fungicide. In some embodiments, the co-fungicide is anilinopyrimidine fungicide. In some embodiments, the co-fungicide is hydroxy-(2-amino)-pyrimidines fungicide. In some embodiments, the co-fungicide is phosphonate fungicide. In some embodiments, the co-fungicide is plant extract fungicide. In some embodiments, the co-fungicide is Keto-Reductase inhibitor fungicide. In some embodiments, the co-fungicide is phenylpyrrole fungicide (PP). In some embodiments, the co-fungicide is aryl phenyl-ketone fungicide. In some embodiments, the co-fungicide in amine fungicide. In some embodiments, the co-fungicide is dinitro aniline fungicide. In some embodiments, the co-fungicide is azanaphthalene fungicide. In some embodiments, the co-fungicide is benzothiadiazole fungicide. In some embodiments, the co-fungicide is carbamate fungicide. In some embodiments, the co-fungicide is cyanoacetamideoxime fungicide. In some embodiments, the co-fungicide is dinitrophenyl-crotonate fungicide. In some embodiments, the co-fungicide is glucopyranosyl antibiotic fungicide. In some embodiments, the co-fungicide is tetrazolyloxime fungicide. In some embodiments, the co-fungicide is thiazolidine fungicide. In some embodiments, the co-fungicide is oxysterol binding protein inhibitor (OSBPI) fungicide. In some embodiments, the co-fungicide is thiophenecarboxamide fungicide. In some embodiments, the co-fungicide is phenylacetamide fungicide. In some embodiments, the co- fungicide is phenyl urea fungicide. In some embodiments, the co-fungicide is polyene fungicide. In some embodiments, the co-fungicide is pyr-hydrazone fungicide. In some embodiments, the co-fungicide is pyrimidinamine fungicide. In some embodiments, the co- fungicide is pyrimidinone fungicide. In some embodiments, the co-fungicide is fungicide (B). In some embodiments, the co-fungicide is heteroaromatic. In some embodiments, the co- fungicide is aromatic hydrocarbon (AH fungicides). In some embodiments, the co-fungicide is quinoxyfen. In some embodiments, the co-fungicide is benzenesulfonamides. In some embodiments, the co-fungicide is probenazole. In some embodiments, the co-fungicide is tridemorph. In some embodiments, the co-fungicide is iprovalicarb. In some embodiments, the co-fungicide is dicarboximide. In some embodiments, the co-fungicide is dithiolane. In some embodiments, the co-fungicide is growth regulator. In some embodiments, the co- fungicide is guanidine. In some embodiments, the co-fungicide is fluoxythioconazole. In some embodiments, the co-fungicide is ipfentrifluconazole. In some embodiments, the co-fungicide is triadimefon. In some embodiments, the co-fungicide is triflumizole. In some embodiments, the co-fungicide is hexopyranosyl antibiotics. In some embodiments, the co-fungicide is bordeaux-mixture. In some embodiments, the co-fungicide is benomyl. In some embodiments, the co-fungicide is Melanin Biosynthesis Inhibitor- Reductase (MBI-R). In some embodiments, the co-fungicide is microbial. In some embodiments, the co-fungicide is n- phenyl carbamate. In some embodiments, the co-fungicide is organo tin compound. In some embodiments, the co-fungicide is oxadixyl. In some embodiments, the co-fungicide is potassium-bicarbonate. In some embodiments, the co-fungicide is potassium-carbonate. In some embodiments, the co-fungicide is polyoxin. In some embodiments, the co-fungicide is fenamidone. In some embodiments, the co-fungicide is metarylpicoxamid. In some embodiments, the co-fungicide is tetracycline antibiotic. In some embodiments, the co- fungicide is uncoupler of oxidative phosphorylation. In some embodiments, the co-fungicide is chlorinconazide. In some embodiments, the co-fungicide is flufenoxadiazam. In some embodiments, the co-fungicide is ipflufenoquin. In some embodiments, the co-fungicide is pyridachlometyl. In some embodiments, the co-fungicide is propamocarb-HCl. In some embodiments, the co-fungicide is propiconazole. In some embodiments, the co-fungicide is benthiavalicarb-isopropyl.

[0009] 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.

[0010] 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.

[0011] 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 from the 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.

[0012] In some embodiments, the phthalimide fungicide is captan. In some embodiments, the phthalimide fungicide is folpet.

[0013] 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.

[0014] 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.

[0015] In some embodiments, the Qil (quinone inside inhibitors) is selected from the group consisting of amisulbrom, cyazofamid, fenpicoxamid and any combination thereof.

[0016] In some embodiments, the Qil (quinone inside inhibitors) is amisulbrom. In some embodiments, the Qil (quinone inside inhibitors) is cyazofamid. In some embodiments, the Qil (quinone inside inhibitors) is fenpicoxamid.

[0017] in some embodiments, the Qol (quinone outside inhibitors) is selected from the group consisting of azoxystrobin, kresoxim-methyl, picoxystrobin, fluxastrobin, dimoxystrobin, pyraciostrobin, trifloxystrobin, coumoxystrobin, fenaminstrobin, pyrametostrobin, triclopyricarb, pyribencarb, pyraoxystrobin, metyltetraprole, mandestrobin, famoxadone, oryzastrobin, enoxastrobin, pyraciostrobin, fiuoxastrobin, flufenostrin, flufenoxystrobin, metominostrobin, triclopyricarb; pyriminostrobin, florylpicoxamid, and any combination thereof. Each alternative represents a separate embodiment.

[0018] In some embodiments, the Qol (quinone outside inhibitors) is azoxystrobin. In some embodiments, the Qol (quinone outside inhibitors) is picoxystrobin.

[0019] In some embodiments, the QoSI (quinone outside stigmatellin inhibitors) is ametoctradin.

[0020] 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.

[0021] In some embodiments, the SDHI fungicide is fluxapyroxad. In some embodiments, the SDHI fungicide is benzovindiflupyr. In some embodiments, the SDHI fungicide is penflufen.

[0022] In some embodiments, the demethylation inhibitor fungicide (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. Each alternative represents a separate embodiment.

[0023] In some embodiments, the DMI is prothioconazole. In some embodiments, the DMI is tebuconazole.

[0024] 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,

[0025] 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.

[0026] 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.[□027] in some embodiments, the keto-reductase inhibitor fungicide is seiected from the group consisting of fenhexamid, fenpyrazamine and a combination thereof. Each alternative represents a separate embodiment.

[0028] in some embodiments the carboxylic acid amide fungicide is selected from the group consisting of benthiavalicarb, dimethomorph, iprovalicard, mandipropamid, valifenalate and any combination thereof. Each alternative represents a separate embodiment.

[0029] in some embodiments, the benzamide fungicide is seiected from the group consisting of fiuopicolide, fiuopimomide, zoxamide and any combination thereof. Each alternative represents a separate embodiment.

[0030] in some embodiments, the benzamide fungicide is fiuopicolide. In some embodiments, the benzamide fungicide is fiuopimomide. in some embodiments, the benzamide fungicide is zoxamide.

[0031] in some embodiments, the phenylpyrrole fungicide is seiected from the group consisting of fludioxonil, fenpiclonil and a combination thereof. Each alternative represents a separate embodiment.

[0032] In some embodiments, the aryl phenyl-ketone fungicide is selected from the group consisting of metrafenone, pyriofenone and any combination thereof.

[0033] 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.

[0034] 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.

[0035] In some embodiments, the azanaphthalene fungicide is proquinazid.

[0036] In some embodiments, the benzothiadiazole fungicide is acibenzolar-S-methyl.

[0037] 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.

[0038] In some embodiments, the cyanoacetamideoxime fungicide is cymoxanil.

[0039] In some embodiments, the dinitrophenyl-crotonate fungicide is meptyldinocap.

[0040] In some embodiments, the glucopyranosyl antibiotic fungicide is validamycin.

[0041] In some embodiments, the tetrazolyloxime fungicide is picarbutrazox.

[0042] In some embodiments, the thiazolidine fungicide is flu tianil.

[0043] in some embodiments, the thiophenecarboxamide fungicide is silthiofam.

[0044] In some embodiments, the natural fungicide is laminarin.

[0045] In some embodiments, the phenylacetamide fungicide is cyflufenamide.

[0046] In some embodiments, the phenyl urea fungicide is pencycuron.

[0047] In some embodiments, the polyene fungicide is natamycin.

[0048] In some embodiments, the pyr-hydrazone fungicide is ferimzone.

[0049] In some embodiments, the pyrimidinamine fungicide is diflumetorim.

[0050] In some embodiments, the anilinopyrimidine fungicide is selected from the group consisting of cyprodinil, mepanipyrim, pyrimethanil and any combination thereof. Each alternative represents a separate embodiment.

[0051] 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.

[0052] 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.

[0053] 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.

[0054] 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.

[0055] 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.

[0056] In some embodiments, the plant extract fungicide is selected from the group consisting of a fungicide extracted from Melaleuca alternifolia, a fungicide extracted fromSwinglea 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.

[0057] In some embodiments, the plant oil is selected from the group consisting of eugenol, geraniol, thymol and any combination thereof.

[0058] In some embodiments, plant extracted fungicide is selected from the group consisting of terpene hydrocarbons, terpene alcohol, terpene phenols and any combination thereof.

[0059] 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.

[0060] In some embodiments, the plant oil is a mixture of eugenol, geraniol, thymol or combination thereof.

[0061] In some embodiments, the heteroaromatics is etridiazole.

[0062] In some embodiments, the AH fungicide is toiclofos-M.

[0063] In some embodiments, the benzenesulfonamide is flusulfamide.

[0064] In some embodiments, the dicarboximide is selected from iprodione and procymidone.

[0065] In some embodiments, the dithiolane is isoprothiolane.

[0066] In some embodiments, the growth regulator is selected from ethephon and paclobutrazol.

[0067] In some embodiments, the guanidine is dodine and dodine free base.

[0068] In some embodiments, the hexopyranosyl antibiotic is kasugamycin.

[0069] In some embodiments, the MBI-R is tricyclazole.

[0070] In some embodiments, the microbial is Bacillus subtilis, Bacillus subtilis strain QST713.

[0071] In some embodiments, the N-phenyl carbamate is diethofencarb.

[0072] In some embodiments, the organo tin compound is fentin, fentin acetate, fentin hydroxide.

[0073] In some embodiments, the tetracycline antibiotic is oxytetracycline.

[0074] In some embodiments, the uncoupler of oxidative phosphorylation is dinocap.

[0075] In some embodiments, the amount of the co-fungicide in the mixture is less than the fungicidal ly effective amount of the co- fungicide when the co- fungicide is used alone.

[0076] In some embodiments, the amount of the compound of Formula I in the mixture is less than the fungicidally effective amount of the compound of Formula I when the compound of Formula I is used alone.

[0077] The term "effective amount" refers to an amount of the active component that is commercially recommended for use to control fungi. The commercially recommended amount for each active component, 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 plant species and the fungus to be controlled.

[0078] In some embodiments, the mixture comprises a compound of Formula I and fluxapyroxad.

[0079] In some embodiments, the mixture comprises a compound of Formula I and prothioconazole.

[0080] In some embodiments, the mixture comprises a compound of Formula I and folpet.

[0081] In some embodiments, the mixture comprises a compound of Formula I and captan.

[0082] In some embodiments, the mixture comprises a compound of Formula I and azoxystrobin.

[0083] In some embodiments, the mixture comprises a compound of Formula I and picoxystrobin.

[0084] In some embodiments, the mixture comprises a compound of Formula I and mancozeb.

[0085] In some embodiments, the mixture comprises a compound of Formula I and mefentrifluconazole.

[0086] In some embodiments, the mixture comprises a compound of Formula I and metconazole.

[0087] In some embodiments, the mixture comprises a compound of Formula I and fluopicolide.

[0088] In the mixtures of this invention, the weight ratio of the compound of Formula I to the co-fungicide lies between 1:400 to 400:1. In the mixtures of this invention, the weight ratio of the compound of Formula I to the co-fungicide lies between 1:300 to 300:1. In the mixtures of this invention, the weight ratio of the compound of Formula I to the co-fungicide lies between 1:200 to 200:1. In the mixtures of this invention, the weight ratio of the compound of Formula I to the co-fungicide lies between 1:100 to 100:1. In the mixtures of this invention,the weight ratio of the compound of Formula I to the co-fungicide lies between 1:200 to 10:1. In some embodiments, the weight ratio of the compound of Formula I to fluxapyroxad lies within the range of between about 1:1.7 and about 1:2.4. in some embodiments, the weight ratio of the compound of Formula I to prothioconazole lies within the range of between about 1:30 and about 3:1. In some embodiments, the weight ratio of the compound of Formula I to folpet lies within the range of between about 1:1.17 and about 1:150. In some embodiments, the weight ratio of the compound of Formula I to captan lies within the range of between about 1:1.5 and about 1:140. In some embodiments, the weight ratio of the compound of Formula I to azoxystrobin lies within the range of between about 1:30 and about 3:1. In some embodiments, the 'weight ratio of the compound of Formula I to picoxystrobin lies within the range of between about 1:13.3 and about 7:1. In some embodiments, the weight ratio of the compound of Formula I to mancozeb lies within the range of between about 1:2.2 and about 1:200. In some embodiments, the weight ratio of the compound of Formula I to mefentrifluconazole lies within the range of between about 1:13.3 and about 3:1. In some embodiments, the weight ratio of the compound of Formula I to metconazole lies within the range of between about 1:13.3 and about 3:1. In some embodiments, the weight ratio of the compound of Formula I to fluopicolide lies within the range of between about 1:13.3 and about 3:1.

[0089] In some embodiments, the mixture is a tank mix.

[0090] The components of the mixture of the present invention can be applied either separately or as part of a multipart fungicidal system.

[0091] 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, fiusilazole, flusulfamide, flutianil, flutolanil, flutriafol, fiuxapyroxad, folpet, formaldehyde, fosetyl, fosetyl -aluminium, fuberidazole, furalaxyl, furametpyr, guazatine, guazatine acetates, GY-81, hexachlorobenzene, hexaconazole, hymexazol, imazalil, imazalil sulfate, imibenconazole, iminoctadine, iminoctadine triacetate, iminoctadine tris(albesilate), iodocarb, ipconazole, ipfenpyrazolone, iprobenfos, iprodione, iprovalicarb, isoprothiolane, isopyrazam, isotianil, kasugamycin, kasugamycin hydrochloride hydrate, kresoxim-methyl, laminarin, mancopper, mancozeb, mandipropamid, maneb, mefenoxam, mepanipyrim, mepronil, meptyl-dinocap, mercuric chloride, mercuric oxide, mercurous chloride, metalaxyl, metalaxyl-M, metam, metam- ammonium, metam-potassium, metam-sodium, metconazole, methasulfocarb, methyl iodide, methyl isothiocyanate, metiram, metominostrobin, metrafenone, mildiomycin, myclobutanil, nabam, nitrothal-isopropyl, nuarimol, octhilinone, ofurace, oleic acid (fatty acids), orysastrobin, oxadixyl, oxine-copper, oxpoconazole fumarate, oxycarboxin, pefurazoate, penconazole, pencycuron, penflufen, pentachlorophenol, pentachlorophenyl laurate, penthiopyrad, phenylmercury acetate, phosphonic acid, phthalide, picoxystrobin, polyoxin B, polyoxins, polyoxorim, potassium bicarbonate, potassium hydroxyquinoline sulfate, probenazole, prochloraz, procymidone, propamocarb, propamocarb hydrochloride, propiconazole, propineb, proquinazid, prothioconazole, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyrazophos, pyribencarb, pyributicarb, pyrifenox, pyrimethanil, pyriofenone, pyroquilon, quinoclamine, quinoxyfen, quintozene, Reynoutria sachalinensis extract, sedaxane, silthiofam, simeconazole, sodium 2- phenylphenoxide, sodium bicarbonate, sodium pentachlorophenoxide, spiroxamine, sulfur, SYP-Z048, tar oils, tebuconazole, tebufloquin, tecnazene, tetraconazole, thiabendazole, thifluzamide, thiophanate-methyl, thiram, tiadinil, tolclofos-methyl, tolylfluanid, triadimefon, triadimenol, triazoxide, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole, validamycin, valifenalate, valiphenal, vinclozolin, zineb, ziram, zoxamide, Candida oleophila, Fusarium oxysporum, Gliocladium spp., Phlebiopsis gigantea, Streptomyces griseoviridis, Trichoderma spp., (RS)-N-(3,5-dichlorophenyl)-2- (methoxymethyl)-succinimide, 1,2-dichloropropane, l,3-dichloro-l,l,3,3-tetrafluoroacetone hydrate, l-chloro-2,4-dinitronaphthalene, 1 -chloro-2-nitropropane, 2-(2-heptadecyl-2- imidazolin- 1 -yl)ethanol, 2,3-dihydro-5-phenyl-l,4-dithi-ine 1,1,4,4-tetraoxide, 2- methoxyethylmercury acetate, 2-methoxyethylmercury chloride, 2-methoxyethylmercury silicate, 3-(4-chlorophenyl)-5-methylrhodanine, 4-(2-nitroprop-l-enyl)phenyl thiocyanateme, ampropylfos, anilazine, azithiram, barium polysulfide, Bayer 32394, benodanil, benquinox, bentaluron, benzamacril; benzamacril-isobutyl, benzamorf, binapacryl, bis(methylmercury) sulfate, bis(tributyltin) oxide, buthiobate, cadmium calcium copper zinc chromate sulfate, carbamorph, CECA, chlobenthiazone, chloraniformethan, chlorfenazole, chlorquinox, climbazole, copper bis(3-phenylsalicylate), copper zinc chromate, cufraneb, cupric hydrazinium sulfate, cuprobam, cyclafuramid, cypendazole, cyprofuram, decafentin, dichlone, dichlozoline, diclobutrazol, dimethirimol, dinocton, dinosulfon, dinoterbon, dipyrithione, ditalimfos, dodicin, drazoxolon, EBP, ESBP, etaconazole, etem, ethirim, fenaminosulf, fenapanil, fenitropan, fluotrimazole, furcarbanil, furconazole, furconazole-cis, furmecyclox, furophanate, glyodine, griseofulvin, halacrinate, Hercules 3944, hexylthiofos, ICIA0858, isopamphos, isovaledione, mebenil, mecarbinzid, metazoxolon, niethfuroxam, methylmercury dicyandiamide, metsulfovax, milneb, mucochloric anhydride, myclozolin, N- 3,5-dichlorophenyl-succinimide, N-3-nitrophenylitaconimide, natamycin, N-ethylmercurio-4- toluenesulfonanilide, nickel bis(dimethyldithiocarbamate), OCH, phenylmercurydimethyldithiocarbamate, phenylmercury nitrate, phosdiphen, prothiocarb; prothiocarb hydrochloride, pyracarbolid, pyridinitril, pyroxychlor, pyroxyfur, quinacetol; quinacetol sulfate, quinazamid, quinconazole, rabenzazole, salicylanilide, SSF-109, sultropen, tecoram, thiadifluor, thicyofen, thiochlorfenphim, thiophanate, thioquinox, tioxymid, triamiphos, triarimol, triazbutil, trichlamide, urbacid, zarilamid, and any combinations thereof.

[0092] The mixtures of the present invention are preferably applied in the form of a composition comprising (a) a compound of Formula I and (b) at least one co-fungicide.

[0093] In some embodiments, the co-fungicide is selected from a group consisting of multisite contact fungicide, Qi I 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 geanus encompasses the species as descrined in the present application.

[0094] 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.

[0095] 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 a fungicide.

[0096] 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 as antifungal agents.

[0097] 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.

[0098] 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.

[0099] 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), a fungicidally effective amount of the mixture or composition described in the present invention. The composition is suitable for treatment of various plants at fungicidal levels, 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.

[0100] 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.

[0101] 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. In some embodiments, the fungal pathogen is one of Mycosphaerella graminicola, Septoria tritici, Puccinia triticina, Puccinia striiformis f. sp. tritici, Venturia inaequalis, Ustilago maydis, Uncinula necator, Rhynchosporium secalis, Magnaporthe grisea, Phakopsora pachyrhizi, Leptosphaeria nodorum, Blumeria graminis f. sp.tritici, Blumeria graminis f. sp. hordei, Erysiphe cichoracearum, Glomerella lagenarium, Cercospora beticola, Alternaria solani, Pyrenophora teres, Ramularia, Peronospora spp., Botrytis cinereal, and Mycosphaerella fijiensis.

[0102] 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.

[0103] 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 (LJncinula 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).

[0104] 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.

[0105] 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, broadleaved trees, or evergreens, for example conifers).

[0106] In some embodiments, the plants are monocotyledonous plants, more preferably, cereals. In a specific embodiment, the cereal crop is wheat. In another specific embodiment, the cereal crop is triticale. In another specific embodiment, the cereal crop is rye. In another specific embodiment, the cereal crop is oat. In a further embodiment, the cereal crop is barley. In another embodiment, the crop plants are rice plants. In still another embodiment, the crop plants are sugar cane plants. In yet another embodiment, the crop plants are corn plants.

[0107] In another embodiment, the crop plants are dicotyledonous plants.

[0108] 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.

[0109] 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.

[0110] 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. Fluxapyroxad is applied at a rate between about 300 g / ha and about 2700 g / ha and the compound of Formula I is applied at a rate between about 30 g / ha and about 300 g / ha. Prothioconazole is applied at a rate between about 50 g / ha and about 450 g / ha and the compound of Formula I is applied at a rate between about 30 g / ha and about 300 g / ha. Folpet is applied at a rate between about 60 g / ha and about 600 g / ha and the compound of Formula I is applied at a rate between about 30 g / ha and about 300 g / ha. Captan is applied at a rate between about 230 g / ha and about 2100 g / ha and the compound of Formula I is applied at a rate between about 30 g / ha and about 300 g / ha.Azoxystrobin is applied at a rate between about 50 g / ha and about 450 g / ha and the compound of Formula I is applied at a rate between about 30 g / ha and about 300 g / ha.Picoxystrobin is applied at a rate between about 20 g / ha and about 180 g / ha and the compound of Formula I is applied at a rate between about 30 g / ha and about 300 g / ha.Mancozeb is applied at a rate between about 250 g / ha and about 2250 g / ha and the compound of Formula I is applied at a rate between about 30 g / ha and about 300 g / ha. Mefentrifluoconazole is applied at a rate between about 50 g / ha and about 450 g / ha and the compound of Formula I is applied at a rate between about 30 g / ha and about 300 g / ha. Metconazole is applied at a rate between about 30 g / ha and about 300 g / ha and the compound of Formula I is applied at a rate between about 30 g / ha and about 300 g / ha. Fluopicolide is applied at a rate between about 30 g / ha and about 300 g / ha and the compound of Formula I is applied at a rate between about 30 g / ha and about 300 g / ha.

[0111] The following examples are provided to further illustrate the invention. They are not meant to be construed as limiting the invention.EXPERIMENTAL SECTIONExample 1The compound of Formula I and Pyridachlometyl were tested straight or in mixture on the Rhizoctonia solani pathogen.Compound of Formula I can be prepared for example as described in publications WO2013 / 025795 and W02021 / 059160.The active ingredients straight or in mixture were diluted in a suitable solvent to a set of concentrations. Two fungicide ratios were tested for each combination between the compound of Formula I and Pyridachlometyl.One hundred microliters of sterile distilled water with or without fungicide were added to 100 si! of pathogen suspension into each well in a microtiter plate (MTP).Experimental DesignEach bioassay was carried out with the following 8 treatment groups corresponding to 8 concentrations of the fungicide mixture. In the MTP assay, 3 replicates (wells) were carried out for each concentration of fungicide mixture.AssessmentsThe MTPs were incubated in the dark at 19°C for 5 days under saturated humidity in order to avoid evaporation. Then, the fungal growth in each well was estimated by measuring the Optical Density (OD) at 590 nm with a BMG plate reader (FLUOstar Omega, BMG Labtech). The OD values at 5 days were automatically corrected by comparison with those measured at day zero (inoculation day). The generated data were transferred to the MARS Data Analysis software (BMG Labtech) which allows to calculate percentage of growth inhibition induced by each concentration of fungicide tested. Finally, the EC5o of each product and mixture was determined.Test validity criteria(i) No bacterial nor fungal contamination at any stage of the assay must be observed.(ii) A normal and constant mycelium growth must be observed in the control wells (without fungicide).(iii) At the end of the evaluation the final minimum OD must reach at least a value of 0.25 Absorbance's Unit (AU).Results

Claims

CLAIMS1. A fungicidal mixture comprising (a) a compound of Formula I and (b) at least one cofungicideFormula I2. The fungicidal mixture of claim 1, wherein the co-fungicide is selected from a group consisting of multi-site contact fungicide, Qi I 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.

3. The fungicidal mixture of claim 1 or 2, wherein the multi-site contact fungicide is selected from a group consisting of phthalimides, thiocarbamate, maleimide, quinoxalines, quinones, triazines, bis-guanidines, sulfamides, chloronitriles, dithiocarbamates, inorganic fungicide and any combination thereof.

4. The fungicidal mixture of claim 3, wherein the Qi I is selected from the group consisting of amisulbrom, cyazofamid, fenpicoxamid and any combination thereof.

5. The fungicidal mixture of claim 3, 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.

6. The fungicidal mixture of claim 3, wherein the the QoS! is ametoctradin.

7. The fungicidal mixture of claim 3, 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.

8. The fungicidal mixture of claim 3, 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.

9. The fungicidal mixture of claim 3, wherein, the phenyl amide fungicide is selected from the group consisting of benalaxyl, metalaxyl, kiralaxyl, mefenoxan, metalaxyl-M and any combination thereof.

10. The fungicidal mixture of claim 3, wherein the MBC fungicide is selected from the group consisting of carbendazim, thiabendazole, thiophanate-methyl and a combination thereof.

11. The fungicidal mixture of claim 3, wherein the carboxylic acid amide fungicide is selected from the group consisting of benthiavalicarb, dimethomorph, iprovalicard, mandipropamid, valifenalate and any combination thereof.

12. The fungicidal mixture of claim 3, wherein the benzamide fungicide is selected from the group consisting of fluopicolide, fluopimomide, zoxamide and any combination thereof.

13. The fungicidal mixture of claim 3, wherein the natural fungicide is laminarin.

14. The fungicidal mixture of claim 3, wherein the anilinopyrimidine fungicide is selected from the group consisting of cyprodinil, mepanipyrim, pyrimethanil and any combination thereof.

15. The fungicidal mixture of claim 3, wherein the hydroxy-(2-amino)-pyrimidines fungicide is selected from the group consisting of bupirimate, dimethirimol, ethirimol and any combination thereof.

16. The fungicidal mixture of claim 3, 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.

17. The fungicidal mixture of claim 3, 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.

18. The fungicidal mixture of claim 3, wherein the keto-reductase inhibitor fungicide is selected from the group consisting of fenhexamid, fenpyrazamine and a combination thereof.

19. The fungicidal mixture of claim 3, wherein the phenylpyrrole fungicide is selected from the group consisting of fludioxonil, fenpiclonil and a combination thereof.

20. The fungicidal mixture of claim 3, wherein the aryl phenyl-ketone fungicide is selected from the group consisting of metrafenone, pyriofenone and any combination thereof.

21. The fungicidal mixture of claim 3, wherein the amine fungicide is selected from the group consisting of fenpropidin, spiroxamine, morpholine and any combination thereof.

22. The fungicidal mixture of claim 3, wherein the dinitro aniline fungicide is selected from the group consisting of fluazinam, 2, 6- dinitro-aniline fungicide, and a combination thereof.

23. The fungicidal mixture of claim 3, wherein the azanaphthalene fungicide is proquinazid.

24. The fungicidal mixture of claim 3, wherein the benzothiadiazole fungicide is acibenzolar-S-methyl.

25. The fungicidal mixture of claim 3, wherein the carbamate fungicide is selected from the group consisting of propamocarb, iodocarb, prothiocarb and any combination thereof.

26. The fungicidal mixture of claim 3, wherein the cyanoacetamideoxime fungicide is cymoxanil.

27. The fungicidal mixture of claim 3, wherein the dinitrophenyl-crotonate fungicide is meptyldinocap.

28. The fungicidal mixture of claim 3, wherein the glucopyranosyl antibiotic fungicide is validamycin,29. The fungicidal mixture of claim 3, wherein the tetrazolyloxime fungicide is picarbutrazox.

30. The fungicidal mixture of claim 3, wherein the thiazol idine fungicide is flutianil.

31. The fungicidal mixture of claim 3, wherein the OSBPI fungicide is selected from the group consisting of fluoxapiprolin, oxathiapiprolin and a combination thereof.

32. The fungicidal mixture of claim 3, wherein the thiophenecarboxamide fungicide is silthiofam.

33. The fungicidal mixture of claim 3, wherein the phenylacetamide fungicide is cyflufenamide.

34. The fungicidal mixture of claim 3, wherein the phenyl urea fungicide is pencycuron.

35. The fungicidal mixture of claim 3, wherein the polyene fungicide is natamycin.

36. The fungicidal mixture of claim 3, wherein the pyr-hydrazone fungicide is ferimzone.

37. The fungicidal mixture of claim 3, wherein the pyrimidinamine fungicide is diflumetorim.

38. The fungicidal mixture of claim 3, wherein heteroaromatics is etridiazole.

39. The fungicidal mixture of claim 3, wherein the AH fungicides is tolclofos-M.

40. The fungicidal mixture of claim 3, wherein the benzenesulfonamides is flusulfamide.

41. The fungicidal mixture of claim 3, wherein the dicarboximide is selected from iprodione and procymidone.

42. The fungicidal mixture of claim 3, wherein the dithiolane is isoprothiolane.

43. The fungicidal mixture of claim 3, wherein the growth regulator is selected from ethephon and paclobutrazol.

44. The fungicidal mixture of claim 3, wherein the guanidine is dodine.

45. The fungicidal mixture of claim 3, wherein the hexopyranosyl antibiotic is kasugamycin.

46. The fungicidal mixture of claim 3, wherein the M Bl-R is tricydazole.

47. The fungicidal mixture of claim 3, wherein the microbial is selected from Bacillus subtilis and Bacillus subtilis strain QST713.

48. The fungicidal mixture of claim 3, wherein the N-phenyl carbamate is diethofencarb.

49. The fungicidal mixture of claim 3, wherein the organo tin compound is selected from fentin, fentin acetate and fentin hydroxide.

50. The fungicidal mixture of claim 3, wherein the tetracycline antibiotic is oxytetracycline.

51. The fungicidal mixture of claim 3, wherein the uncoupler of oxidative phosphorylation is dinocap.

52. The fungicidal mixture of any one of claims 1-51, wherein the amount of the cofungicide in the mixture is less than the fungicidally effective amount of the cofungicide when the co- fungicide is used alone, and / or the amount of the compound of Formula I in the mixture is less than the fungicidally effective amount of the compound of Formula I when the compound of Formula I is used alone.

53. The fungicidal mixture of any one of claims 1-52, further comprising at least one pesticide.

54. The fungicidal mixture of any one of claims 1-53, wherein the mixture is a tank mix.

55. A composition comprising the mixture of any one of claims 1-54.

56. A method for treating a plant or locus against fungal infection comprising applying (a) a compound of Formula I and (b) at least one co-fungicide.

57. The method of claim 56, wherein the co-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.

58. A method for treating a plant or locus against fungal infection comprising applying the mixture or composition of any one of claims 1-55 to the plant or locus so as to thereby treat the plant or locus against fungal infection.

59. A method for the control or prevention of fungal attack comprising applying to the locus of the fungus, or to a locus in which the infestation is to be prevented a fungicidal ly effective amount of the mixture or composition of any one of claims 1- 55.

60. Use of the mixture or composition of any one of claims 1-55 for treating a plant or locus against fungal infection.

61. Use of the mixture or composition of any one of claims 1-55 for controlling or preventing a fungal attack,62. The mixture or composition of any one of claims 1-55 for use to treat a plant or locus against fungal infection.

Citation Information

Patent Citations

  • Process for preparing 5-(fluoro-4-imino-3-methyl)-1-tosyl-3,4 dihydropyrimidine -(1H)-one

    WO2021059160A1

  • Composition for controlling plant diseases and use thereof

    US20150038327A1

  • 5-fluoro-4-imino-3-(substituted)-3,4-dihydropyrimidin-2-(1 h)-one derivatives

    WO2013025795A1