Mixture of succinate dehydrogenase inhibitor and picolinamide

Abstract

A composition comprising (a1) a succinate dehydrogenase inhibitor (SDHI) and (a2) a picolinamide is disclosed. Also disclosed is a method for controlling plant diseases caused by fungal plant pathogens, the method comprising applying to a plant or a part thereof, or to a plant seed, a fungicidally effective amount of a composition comprising (a1) a succinate dehydrogenase inhibitor (SDHI) and (a2) a picolinamide.

Description

[Technical Field]

[0001] The present invention relates to pesticide compositions comprising mixtures comprising a succinate dehydrogenase inhibitor (SDHI) and a picolinamide, and methods of using such mixtures to protect plants or plant seeds from diseases caused by fungal pathogens. [Background technology]

[0002] Control of plant diseases caused by fungal plant pathogens is crucial in achieving high crop efficiency. Plant disease damage to ornamental plants, vegetables, field, cereal, and fruit crops can cause significant losses in productivity, thereby resulting in increased costs to consumers. In addition to being highly destructive in many cases, plant diseases can be difficult to control and can develop resistance to commercially available fungicides. While many products are available on the market for these purposes, there remains a need for new fungicidal compounds that are more effective, less costly, less toxic, environmentally safer, or have different sites of action. In addition to the introduction of new fungicides, combinations of fungicides are often used to promote disease control, broaden the spectrum of control, and delay resistance development. Furthermore, certain unusual combinations of fungicides demonstrate greater-than-additive (i.e., synergistic) effects to provide commercially important levels of plant disease control. It is recognized in the art that the benefits of a particular fungicide combination will vary, depending on factors such as the particular plant species and the plant disease being treated, whether the plant disease is caused by a resistant strain of fungus, and whether the plant is treated before or after infection with a fungal plant pathogen. Thus, new advantageous combinations are needed to provide a variety of options for best meeting specific plant disease control requirements. Such combinations have now been discovered.

[0003] PCT Patent Publications WO 2012 / 084812 and WO 2013 / 186325 disclose certain succinate dehydrogenase inhibitors (SDHIs) selected from pyrazole-4-carboxamide derivatives, mixtures thereof, and their use as fungicides.

[0004] PCT Patent Publication WO 2007 / 048556 discloses certain succinate dehydrogenase inhibitors (SDHIs) selected from heterocyclic amide derivatives, mixtures thereof, and their use as fungicides.

[0005] US Patent Application Publication No. 2008 / 0293798 discloses fungicidal mixtures comprising a succinate dehydrogenase inhibitor (SDHI) selected from 1-methylpyrazol-4-ylcarboxanilide derivatives.

[0006] PCT Patent Publications WO 2003 / 035617, WO 2016 / 109257, WO 2018 / 129237, and WO 2019 / 173665 disclose picolinamide compounds, mixtures thereof, and their use as fungicides. Summary of the Invention [Means for solving the problem]

[0007] The present invention provides a fungicidal composition (i.e., combination, mixture) comprising: (a1) a succinate dehydrogenase inhibitor (SDHI); (a2) picolinamide, The present invention relates to a composition comprising:

[0008] The present invention also relates to a composition comprising: (a1) a succinate dehydrogenase inhibitor (SDHI); (a2) a picolinamide; and at least one component (b).

[0009] The present invention also relates to a composition comprising: (a1) a succinate dehydrogenase inhibitor (SDHI); and (a2) a picolinamide, wherein the SDHI and picolinamide are present in a synergistically effective amount, and optionally at least one component (b).

[0010] The present invention also relates to compositions comprising one of the compositions described above and at least one additional component selected from the group consisting of surfactants, solid diluents, and liquid diluents.

[0011] The present invention also relates to a method for controlling plant diseases caused by fungal plant pathogens, including resistant strains of fungal pathogens, comprising applying to a plant or part thereof or to seeds of the plant a fungicidally effective amount of one of the above compositions.

[0012] The above method may also be described as a method of protecting a plant or a plant seed from disease caused by a fungal plant pathogen, comprising applying to the plant (or a part thereof) or plant seed (either directly or through the environment (e.g., growth medium) of the plant or plant seed) a fungicidally effective amount of one of the compositions. DETAILED DESCRIPTION OF THE INVENTION

[0013] As used herein, the terms "comprises," "comprising," "includes," "including," "has," "having," "contains," "containing," "characterized by," or any variation thereof, are intended to include a non-exclusive inclusion, subject to any limitations expressly indicated. For example, a composition, mixture, process, method, article, or device that includes a list of elements is not necessarily limited to only those elements and may include other elements not expressly listed or inherent in such composition, mixture, process, method, article, or device.

[0014] The transitional phrase "consisting of" excludes any unspecified element, step, or ingredient. In claims, when a claim is closed to encompass substances different from those recited, apart from impurities, it is usually relevant thereto. When the phrase "consisting of" appears in a clause in the body of a claim rather than immediately following the preamble, it limits only the elements recited in that clause; other elements are not excluded from the claim as a whole.

[0015] The transitional phrase "consisting essentially of" is used to define a composition, method, or apparatus that includes materials, steps, features, ingredients, or elements in addition to those literally disclosed, provided that these additional materials, steps, features, ingredients, or elements do not materially affect the basic and novel characteristics of the claimed invention. The term "consisting essentially of" occupies a neutral position between "comprising" and "consisting of."

[0016] It should be readily understood that where an applicant defines an invention or part thereof with open-ended terms such as "comprising," the description should (unless otherwise expressly stated) be construed as also describing such inventions using the terms "consisting essentially of" or "consisting of."

[0017] Furthermore, unless expressly stated to the contrary, "or" refers to an inclusive "or" and not an exclusive "or." For example, a condition A or B is satisfied by any one of the following: A is true (or exists) and B is false (or does not exist), A is false (or does not exist) and B is true (or exists), and both A and B are true (or exist).

[0018] Furthermore, the indefinite articles "a" and "an" preceding an element or component of the invention are intended to be open-ended regarding the number of instances (i.e., occurrences) of that element or component. Thus, "a" or "an" should be read to include one or at least one, and singular forms of elements or components also include the plural, unless the number is clearly intended to be singular.

[0019] The term "agricultural" refers to the production of agricultural crops such as food and fiber, and includes the growing of corn or maize, soybeans and other legumes, rice, grains (e.g., wheat, oats, barley, rye, and rice), leafy vegetables (e.g., lettuce, cabbage, and other greens), fruit vegetables (e.g., tomatoes, peppers, eggplant, crucifers, and cucurbits), potatoes, sweet potatoes, grapes, cotton, fruit trees (e.g., pome fruits, stone fruits, and citrus fruits), small fruit trees (e.g., berries and cherries), and other specialty crops (e.g., canola, sunflowers, and olives).

[0020] The term "non-agricultural" refers to non-crop crops such as horticultural crops (e.g., greenhouse, nursery, or ornamental plants not grown in a field), residential, agricultural, commercial, and industrial structures, turf (e.g., turf farms, pastures, golf courses, lawns, athletic fields, etc.), wood products, storage products, silviculture and vegetation management, public health (i.e., humans) and animal health (e.g., domesticated animals, e.g., pets, livestock, and poultry, non-domesticated animals such as wildlife) uses.

[0021] The term "crop vigor" refers to the rate of growth or biomass deposition in a crop plant. "Increased vigor" refers to an increase in growth or biomass deposition in a crop plant compared to an untreated control crop plant. The term "crop yield" refers to the harvest of crop material, both in terms of quantity and quality, obtained after harvesting the crop plant. "Increased crop yield" refers to an increase in crop yield compared to an untreated control crop plant.

[0022] The term "biologically effective amount" refers to an amount of a biologically active compound sufficient to produce a desired biological effect upon application (i.e., contact) to the fungi to be controlled or their environment or to the plant, seed or locus of the plant in which the plant grows (e.g., growth medium) for protecting the plant from damage by fungal disease or for other desired effect (e.g., increased plant vigor).

[0023] As referred to in this disclosure and claims, "plants" include members of the Kingdom Plantae, particularly Spermatopsida, in all life stages, including seedlings (e.g., germinating seeds that grow into seedlings) and mature, reproductive growth stages (e.g., plants that produce flowers and seeds). Plant parts include geotropic members that typically grow below the surface of the growing medium (e.g., soil), such as rhizomes, tubers, bulbs, and corms, and above the surface of the growing medium (e.g., soil), such as leaves (including stems and leaves), flowers, fruits, and seeds.

[0024] As referred to herein, the term "seedling", used alone or in combination, means a young plant developing from the germ of a seed.

[0025] As referred to herein, the term "broadleaf" used alone or in terms such as "broadleaf crops" means dicotyledonous or dicotyledonous plants, the term being used to describe a group of angiosperms characterized by an embryo with two cotyledons.

[0026] As referred to in this disclosure, the terms "fungal pathogen" and "fungal plant pathogen" include pathogens of the phyla Ascomycota, Basidiomycota, and Zygomycota, as well as fungus-like Oomycota, which are causative agents of a wide spectrum of plant diseases of economically important ornamentals, turf, vegetables, field, grain, and fruit crops. In the context of this disclosure, "protecting plants from disease" or "controlling plant diseases" includes preventative action (interruption of the fungal cycle of infection, colonization, symptom development, and sporulation) and / or therapeutic action (inhibition of colonization of plant host tissue).

[0027] As used herein, the term "mode of action" (MOA), as defined by the Fungicide Resistance Action Committee (FRAC), is used to distinguish fungicides by their biochemical mechanism of action in the biosynthetic pathway of plant pathogens and their risk of resistance. FRAC-defined modes of action include: (A) nucleic acid synthesis, (B) mitosis and cell division, (C) respiration, (D) amino acid and protein synthesis, (E) signal transduction, (F) lipid synthesis and membrane integrity, (G) membrane sterol biosynthesis, (H) cell wall biosynthesis, (I) cell wall melanin synthesis, (P) host plant defense induction, (U) unknown mechanism of action, (NC) unclassified, (M) chemicals with multi-site activity, and (BM) biologicals with multiple mechanisms of action. Each mechanism of action (i.e., letters A-BM) contains one or more subgroups (e.g., A includes subgroups A1, A2, A3, and A4) based on individual confirmed target sites of action or, if the exact target site is unknown, based on cross-resistance profiles within the group or with respect to other groups. Each of these subgroups (e.g., A1, A2, A3, and A4) is assigned a FRAC code, which is a number and / or letter. For example, the FRAC code for subgroup A1 is 4. Additional information regarding target sites and FRAC codes can be obtained, for example, from publicly available databases provided by FRAC.

[0028] As used herein, the term "cross-resistance" refers to the phenomenon that occurs when a pathogen develops resistance to one fungicide and simultaneously becomes resistant to one or more other fungicides, which are typically, but not always, in the same chemical class, have the same target site of action, or are antidoteable by the same mechanism.

[0029] In this disclosure, phrases such as "fungicide resistance" or "resistant strain of fungus" refer to fungal pathogens that survive and reproduce in the presence of a fungicide. Resistance development is an evolutionary process that occurs after a period of exposure of a pathogen to a fungicide. For example, a pathogen that is initially susceptible to a fungicide becomes less susceptible over time and is no longer adequately controlled by the fungicide. Resistance can occur as qualitative or quantitative resistance. Quantitative resistance, also known as single-gene or major-gene resistance, occurs when a single mutation in a target gene results in loss of efficacy. Quantitative resistance, also known as multigene resistance, occurs when the occurrence of many individual genetic changes, such as mutations in or overexpression of a target gene, results in a gradual decrease in susceptibility. Additional information regarding fungal species resistant to fungicides and corresponding genetic mutations is periodically published by FRAC and is publicly available on its website.

[0030] The compounds of the present invention can exist as one or more stereoisomers. Stereoisomers are isomers that have identical constitution but differ in the spatial arrangement of their atoms, and include enantiomers, diastereomers, cis- and trans-isomers (also known as geometric isomers), and atropisomers. Atropisomers result from restricted rotation around a single bond, and the high barrier to rotation makes it possible to isolate these isomeric species. As will be appreciated by those skilled in the art, one stereoisomer may be more reactive and / or may exhibit advantageous effects when enriched or separated from other stereoisomers. Furthermore, those skilled in the art will recognize methods for separating, enriching, and / or selectively preparing such stereoisomers. For a comprehensive description of all aspects of stereoisomerism, see Ernest L. Eliel and Samuel H. Wilen, Stereochemistry of Organic Compounds, John Wiley & Sons, 1994.

[0031] The present invention also includes compounds of the listed formulas that are enriched in one stereoisomer relative to other stereoisomers. For example, the ratio of (Z)- to (E)-isomers in any compound of the listed formulas, whether produced stereoselectively or non-stereoselectively, can have a wide range of values. Additionally, the present invention includes compounds of the listed formulas that are enriched in enantiomers relative to racemic mixtures. Essentially pure enantiomers of compounds of the listed formulas are also included. Enantiomerically enriched means that one enantiomer is present in greater amount than the other, and the degree of enrichment can be defined in terms of enantiomeric excess ("ee"), which is defined as (2x-1)*100%, where x is the mole fraction of the major enantiomer in the mixture (e.g., 20% "ee" corresponds to a 60:40 enantiomeric ratio).

[0032] The compositions of the invention may have an enantiomeric excess of the more active isomer of at least 50%; at least 75%; or at least 90%; or at least 94%.

[0033] The compounds of the present invention may exist as one or more conformers due to restricted rotation about the amide bond (e.g., C(=O)-N) in the listed formula (or listed chemical name). The present invention also includes mixtures of conformers. In addition, the present invention also includes compounds enriched in one conformer relative to another.

[0034] The present invention includes all stereoisomers, structural isomers and mixtures thereof in all proportions as well as isotopic forms such as deuterated compounds.

[0035] Those skilled in the art will understand that not all nitrogen-containing heterocycles can form N-oxides because the nitrogen requires an available lone pair of electrons to be oxidized to the oxide. Those skilled in the art will recognize those nitrogen-containing heterocycles that can form N-oxides. Those skilled in the art will also be familiar with the ability of tertiary amines to form N-oxides. Synthetic methods for preparing N-oxides of heterocycles and tertiary amines are very familiar to those skilled in the art, including the oxidation of heterocycles and tertiary amines using peroxyacids such as peracetic acid and m-chloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxides such as t-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethyldioxirane.These methods for preparing N-oxides have been widely described and reviewed in the literature, see, for example, the following references: T.L.G. Ilchrist, Comprehensive Organic Synthesis, vol. 7, pp. 748-750 (S.V. Ley, Ed., Pergamon Press); M. Tisler and B. Stanovnik, Comprehensive Heterocyclic Chemistry, vol. 3, pp. 18-20, A.J. Boulton and A. McKillop, Eds., Pergamon Press; M.R. Grimmett and B.R.T. Keene, Advances in Heterocyclic Chemistry, vol. 43, pp. 149-161, A.R.Katrittzky, Eds., Academic Press; M. Tisler and B. Stanovnik, Advances in Heterocyclic Chemistry, vol. 9, pp. 285-291, A.R.Katrittzky and A.J.Boulton, Eds., Academic Press. Press; and GWHCheeseman and ESGWerstiuk, Advances in Heterocyclic Chemistry, vol. 22, pp. 390-392, ARKatritzky and AJ Boulton, Eds., Academic Press.

[0036] Those skilled in the art recognize that salts of compounds share the biological utility of their corresponding non-salt forms because, under environmental and physiological conditions, salts are in equilibrium with their corresponding non-salt forms. Thus, a wide variety of salts of compounds of the recited formulas (or recited chemical names) are useful for controlling plant diseases caused by fungal plant pathogens (i.e., suitable as pesticides). Salts of compounds of the recited formulas include acid addition salts with inorganic or organic acids, such as hydrobromic acid, hydrochloric acid, nitric acid, phosphoric acid, sulfuric acid, acetic acid, butyric acid, fumaric acid, lactic acid, maleic acid, malonic acid, oxalic acid, propionic acid, salicylic acid, tartaric acid, 4-toluenesulfonic acid, or valeric acid. When a compound of the recited formula contains an acidic residue, such as a carboxylic acid, salts also include, for example, hydroxides or carbonates of pyridine, triethylamine, or ammonia, or amides, hydrides, sodium, potassium, lithium, calcium, magnesium, or barium. Thus, the present invention includes compounds of the recited formulae, their N-oxides and pesticidal salts and solvates.

[0037] Compounds of the recited formulas, their stereoisomers, tautomers, N-oxides, and salts typically exist in more than one form; therefore, the recited formulas include all crystalline and amorphous forms of the compounds represented by the recited formulas. Amorphous forms include solid embodiments, such as waxes and gums, as well as liquid embodiments, such as solutions and melts. Crystalline forms include embodiments that exhibit a substantially single crystal type and embodiments that exhibit a mixture of polymorphs (i.e., multiple crystalline types). The term "polymorph" refers to a particular crystalline form of a compound that can crystallize in various crystalline forms, these forms having different molecular arrangements and / or conformations in the crystal lattice. Multiple polymorphs can have the same chemical composition, but they can also differ in composition due to the presence or absence of co-crystallized water or other molecules that may be weakly or strongly bound in the lattice. Polymorphs can differ in chemical, physical, and biological properties, such as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspendability, dissolution rate, and bioavailability. Those skilled in the art will understand that a particular polymorph of a compound represented by a recited formula may exhibit advantageous effects (e.g., suitability in preparing useful formulations, improved biological performance) compared to other polymorphs or mixtures of polymorphs of the same compound represented by the recited formula. The preparation and isolation of a particular polymorph of a compound represented by a recited formula can be achieved by methods known to those skilled in the art, such as, for example, crystallization using selected solvents and temperatures. For a comprehensive discussion of polymorphism, see R. Hilfiker, Ed., Polymorphism in the Pharmaceutical Industry, Wiley-VCH, Weinheim, 2006.

[0038] As described in the Summary of the Invention, one aspect of the present invention relates to a composition comprising (a1) a succinate dehydrogenase inhibitor (SDHI), (a2) a picolinamide, and at least one component (b). More particularly, the at least one component (b) is: (b1) methyl benzimidazole carbamate (MBC) fungicide, (b2) dicarboximide fungicides, (b3) demethylation inhibitor (DMI) fungicides; (b4) phenylamide (PA) fungicides, (b5) amine / morpholine fungicides, (b6) phospholipid biosynthesis inhibitor fungicides, (b7) an additional succinate dehydrogenase inhibitor (SDHI) fungicide; (b8) hydroxy(2-amino-)pyrimidine fungicides, (b9) Anilinopyrimidine (AP) fungicides, (b10) N-phenylcarbamate fungicides, (b11) Quinone Outside Inhibitor (QoI) fungicides, (b12) phenylpyrrole (PP) fungicides, (b13) azanaphthalene fungicides, (b14) cell peroxidation inhibitors fungicides, (b15) melanin biosynthesis inhibitor-reductase (MBI-R) fungicides; (b16a) melanin biosynthesis inhibitor-dehydratase (MBI-D) fungicides, (b16b) Melanin biosynthesis inhibitor-polyketide synthase (MBI-P) fungicides, (b17) ketoreductase inhibitor (KRI) fungicides, (b18) squalene-epoxidase inhibitor fungicides, (b19) polyoxin fungicides, (b20) phenylurea fungicides, (b21) quinone inside inhibitor (QiI) fungicides, (b22) benzamide and thiazolecarboxamide fungicides, (b23) enopyranuronic acid antibiotic fungicides, (b24) hexopyranosyl antibiotic fungicides, (b25) glucopyranosyl antibiotics: protein synthesis fungicides, (b26) glucopyranosyl antibiotic fungicides, (b27) cyanoacetamide oxime fungicides, (b28) carbamate fungicides, (b29) oxidative phosphorylation uncoupling fungicides, (b30) organotin fungicides, (b31) carboxylic acid fungicides, (b32) heterocyclic aromatic compound fungicides, (b33) phosphonate fungicides, (b34) phthalamic acid fungicides, (b35) benzotriazine fungicides, (b36) benzene-sulfonamide fungicides, (b37) pyridazinone fungicides, (b38) thiophene-carboxamide fungicides, (b39) Complex I NADH oxidoreductase inhibitor fungicide, (b40) carboxylic acid amide (CAA) fungicides, (b41) tetracycline antibiotic fungicides, (b42) thiocarbamate fungicides, (b43) benzamide fungicides, (b44) microbial fungicides, (b45) quinone outside inhibitor, stigmatellin binding (QoSI) fungicides, (b46) plant extract fungicides, (b47) cyanoacrylate fungicides, (b48) polyene fungicides, (b49) oxysterol binding protein inhibitor (OSBPI) fungicides, (b50) aryl-phenyl-ketone fungicides, (b51) host plant defense-inducing fungicides, (b52) multi-site active fungicides, (b53) Biological agents with multiple mechanisms of action; (b54) Fungicides other than the fungicides of component (a1), component (a2), and components (b1) to (b53), and Salts of compounds (b1) to (b54) is selected from the group consisting of:

[0039] Of note are embodiments in which component (b) comprises at least one fungicidal compound from each of two different groups selected from (b1) through (b54).

[0040] "Methyl benzimidazole carbamate (MBC) fungicide (b1)" (FRAC code 1) inhibits mitosis by binding to β-tubulin during microtubule assembly. Inhibition of microtubule assembly can disrupt cell division, intracellular transport, and cellular structure. Methyl benzimidazole carbamate fungicides include benzimidazole and thiophanate fungicides. Benzimidazoles include benomyl, carbendazim, fuberidazole, and thiabendazole. Thiophanates include thiophanate and thiophanate-methyl.

[0041] "Dicarboximide fungicides (b2)" (FRAC code 2) inhibit mitogen-activated protein (MAP) / histidine kinase in osmotic signaling. Examples include chlozolinate, dimethaclon, iprodione, procymidone, and vinclozolin.

[0042] "Demethylation inhibitor (DMI) fungicides (b3)" (FRAC code 3) (sterol biosynthesis inhibitors (SBI): class I) inhibit the C14 demethylase involved in sterol production. Sterols, such as ergosterol, are required for membrane structure and function and are therefore essential for the development of a functional cell wall. Exposure to these fungicides therefore results in the overgrowth and eventual death of susceptible fungi. DMI fungicides are divided into several chemical classes: piperazines, pyridines, pyrimidines, imidazoles, triazoles, and triazolinethiones. Piperazines include trifoline. Pyridines include buthiobate, pyrifenox, pyrisoxazole, and (αS)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-4-isoxazolyl]-3-pyridineemethanol. Pyrimidines include fenarimol, nuarimol and triarimol. Imidazoles include econazole, imazalil, oxpoconazole, pefurazoate, prochloraz and triflumizole.Triazoles include azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole (including diniconazole-M), epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, ipfentrifluconazole, mefentrifluconazole, metconazole, myclobutanil, penconazole, propiconazole, quinconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, uniconazole, uniconazole-P, α-(1-chlorocyclopropyl)-α-[2-(2-methylpropyl)-2-methyl ... Triazolinethiones include prothioconazole. Biochemical investigations have shown that all of the above fungicides are DMI fungicides as described by KH Kuck et al. in Modern Selective Fungicides - Properties, Applications and Mechanisms of Action, H. Lyr (Ed.), Gustav Fischer Verlag: New York, 1995, pp. 205-258.

[0043] "Phenylamide (PA) fungicides (b4)" (FRAC code 4) are specific inhibitors of RNA polymerase in Oomycete fungi. Susceptible fungi exposed to these fungicides exhibit a reduced ability to incorporate uridine into rRNA. Exposure to this class of fungicide inhibits the growth and development of susceptible fungi. Phenylamide fungicides include acylalanine, oxazolidinone, and butyrolactone fungicides. Acylalanines include benalaxyl, benalaxyl-M (also known as chiralaxyl), furalaxyl, metalaxyl, and metalaxyl-M (also known as mefenoxam). Oxazolidinones include oxadixyl. Butyrolactones include ofrace.

[0044] "Amine / morpholine fungicides (b5)" (FRAC code 5) (SBI: class II) target two sites in the sterol biosynthetic pathway, Δ 8 →Δ 7 Isomerase and Δ 14 They inhibit reductase. Sterols, such as ergosterol, are required for membrane structure and function and are therefore essential for the development of functional cell walls. Therefore, exposure to these fungicides results in the overgrowth and eventual death of susceptible fungi. Amine / morpholine fungicides (also known as non-DMI sterol biosynthesis inhibitors) include morpholine, piperidine, and spiroketal-amine fungicides. Morpholines include aldimorph, dodemorph, fenpropimorph, tridemorph, and trimorphamide. Piperidines include fenpropidin and piperaline. Spiroketal amines include spiroxamine.

[0045] "Phospholipid biosynthesis inhibitor fungicides (b6)" (FRAC code 6) inhibit the growth of fungi by affecting the biosynthesis of phospholipids. Phospholipid biosynthesis inhibitor fungicides include phosphorothiolate fungicides and dithiolane fungicides. Phosphorothiolates include edifenphos, iprobenfos and pyrazophos. Dithiolanes include isoprothiolane.

[0046] "Succinate dehydrogenase inhibitor (SDHI) fungicides (b7)" (FRAC code 7) inhibit the respiration of Complex II fungi by inhibiting succinate dehydrogenase, a key enzyme in the Krebs cycle (TCA cycle). When respiration is inhibited, fungi are unable to produce ATP, resulting in impaired growth and reproduction. SDHI fungicides include phenylbenzamide, phenyloxoethylthiophenamide, pyridinylethylbenzamide, furancarboxamide, oxathiinecarboxamide, thiazolecarboxamide, pyrazole-4-carboxamide, N-cyclopropyl-N-benzyl-pyrazolecarboxamide, N-methoxy-(phenyl-ethyl)-pyrazolecarboxamide, pyridinecarboxamide, and pyrazinecarboxamide fungicides. Phenylbenzamides include benodanil, flutolanil, and mepronil. The phenyloxoethylthiophenamides include isofetamide. The pyridinylethylbenzamides include fluopyram. The furancarboxamides include fenfuram. The oxathiincarboxamides include carboxin and oxycarboxin. The thiazolecarboxamides include thifluzamide. Pyrazole-4-carboxamides include benzovindiflupyr, bixafen, fluveneteram (tentative name, registration number 1676101-39-5), fluindapyr, fluxapyroxad, furametpyr, inpirfluxam, isopyrazam, penflufen, penthiopyrad, pyrapropoin (tentative name, registration number 1803108-03-3), sedaxane, and N-[2-(2,4-dichlorophenyl)-2-methoxy-1-methylethyl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide. N-cyclopropyl-N-benzyl-pyrazolecarboxamides include isoflucipram. N-methoxy-(phenylethyl)-pyrazolecarboxamides include pydiflumetofen. Pyridinecarboxamides include boscalid. Pyrazinecarboxamides include pyraziflumide.

[0047] "Hydroxy(2-amino)pyrimidine fungicides (b8)" (FRAC code 8) inhibit nucleic acid synthesis by inhibiting adenosine deaminase. Examples include bupirimate, dimethirimol, and ethirimol.

[0048] "Anilinopyrimidine (AP) fungicides (b9)" (FRAC code 9) are proposed to inhibit the biosynthesis of the amino acid methionine and to inhibit the secretion of hydrolytic enzymes that lyse plant cells upon infection. Examples include cyprodinil, mepanipyrim, and pyrimethanil.

[0049] "N-phenylcarbamate fungicides (b10)" (FRAC code 10) inhibit mitosis by binding to beta-tubulin and disrupting microtubule assembly. Inhibition of microtubule assembly can disrupt cell division, intracellular transport, and cellular structure. Examples include diethofencarb.

[0050] Quinone outside inhibitor (QoI) fungicides (b11) (FRAC code 11) inhibit complex III of fungal mitochondrial respiration by affecting ubiquinol oxidase. Oxidation of ubiquinol is inhibited at the "quinone outside" (Qo) site of the cytochrome bc1 complex present in the inner mitochondrial membrane of fungi. Inhibition of mitochondrial respiration prevents normal growth and development of fungi. Quinone outside inhibitor fungicides include methoxyacrylate, methoxyacetamide, methoxycarbamate, oximinoacetate, oximinoacetamide, and dihydrodioxazine fungicides (collectively known as strobilurin fungicides), oxazolidinedione, imidazolinone, benzyl carbamate, and tetrazolinone (subgroup A) fungicides. Methoxyacrylates include azoxystrobin, cumoxystrobin, enoxastrobin (also known as enestrobin), flufenoxystrobin, picoxystrobin, and pyraoxystrobin. Methoxyacetamides include mandestrobin. Methoxycarbamates include pyraclostrobin, pyrametostrobin, and triclopyricarb. Oximinoacetates include kresoxim-methyl and trifloxystrobin. Oximinoacetamides include dimoxystrobin, phenaminestrobin, metominostrobin, and orysastrobin. Dihydrodioxazines include fluoxastrobin. Oxazolidinediones include famoxadone. Imidazolinones include fenamidone. Benzylcarbamates include pyribencarb. Tetrazolinones include methyltetraprole.

[0051] "Phenylpyrrole (PP) fungicides (b12)" (FRAC code 12) inhibit MAP / histidine kinases involved in osmotic signaling in fungi. Fenpiclonil and fludioxonil are examples of this class of fungicides.

[0052] "Azanaphthalene fungicides (b13)" (FRAC code 13) are proposed to inhibit signal transduction by an unknown mechanism. They have been shown to interfere with germination and / or appressorium formation of fungi that cause powdery mildew diseases. Azanaphthalene fungicides include aryloxyquinolines and quinazolinones. Aryloxyquinolines include quinoxyfen. Quinazolinones include proquinazide.

[0053] "Cellular peroxidation inhibitor fungicides (b14)" (FRAC code 14) have been proposed to inhibit lipid peroxidation, which affects membrane synthesis in fungi. Members of this class, such as etridiazole, may also affect other biological processes, such as respiration and melanin biosynthesis. Cellular peroxidation fungicides include aromatic hydrocarbon and 1,2,4-thiadiazole fungicides. Aromatic hydrocarbon fungicides include biphenyl, chloroneb, dicloran, quintozene, tecnazene, and tolclofos-methyl. 1,2,4-thiadiazoles include etridiazole.

[0054] "Melanin biosynthesis inhibitor-reductase (MBI-R) fungicides (b15)" (FRAC code 16.1) inhibit the naphthalene reduction step of melanin biosynthesis. Melanin is required for infection of host plants by some fungi. Melanin biosynthesis inhibitor-reductase fungicides include isobenzofuranones, pyrroloquinolinones, and triazolobenzothiazole fungicides. Isobenzofuranones include phthalides. Pyrroloquinolinones include pyroquilon. Triazolobenzothiazoles include tricyclazole.

[0055] "Melanin biosynthesis inhibitor-dehydratase (MBI-D) fungicides (b16a)" (FRAC code 16.2) inhibit scytalone dehydratase in melanin biosynthesis. Melanin is required for infection of host plants by some fungi. Melanin biosynthesis inhibitor-dehydratase fungicides include cyclopropanecarboxamide, carboxamide, and propionamide fungicides. Cyclopropanecarboxamides include carpropamid. Carboxamides include diclocymet. Propionamides include fenoxanil.

[0056] "Melanin biosynthesis inhibitor-polyketide synthase (MBI-P) fungicides (b16b)" (FRAC code 16.3) are compounds that inhibit polyketide synthase in melanin biosynthesis. Melanin is required for infection of host plants by some fungi. Melanin biosynthesis inhibitor-polyketide synthase fungicides include trifluoroethylcarbamate fungicides. Trifluoroethylcarbamate fungicides include tolprocarb.

[0057] "Ketoreductase inhibitor (KRI) fungicides (b17)" (FRAC code 17) inhibit 3-ketoreductase during C4-demethylation in sterol production. Ketoreductase inhibitor fungicides (also known as sterol biosynthesis inhibitors (SBI): class III) include hydroxyanilides and aminopyrazolinones. Hydroxyanilides include fenhexamid. Aminopyrazolinones include fenpyrazamine. In addition, quinofumelin (tentative name, registration number 861647-84-9) and ipflufenoquin (tentative name, registration number 1314008-27-9) are considered to be ketoreductase-inhibiting fungicides.

[0058] "Squalene-epoxidase inhibitor fungicides (b18)" (FRAC code 18) (SBI: Class IV) inhibit squalene epoxidase in the sterol biosynthetic pathway. Sterols, such as ergosterol, are required for membrane structure and function and are therefore essential for the development of a functional cell wall. Therefore, exposure to these fungicides results in the overgrowth and eventual death of susceptible fungi. Squalene epoxidase inhibitor fungicides include thiocarbamate fungicides and allylamine fungicides. Thiocarbamates include pyributicarb. Allylamines include naftifine and terbinafine.

[0059] "Polyoxin fungicides (b19)" (FRAC code 19) inhibit chitin synthase. Examples include polyoxins.

[0060] "Phenyleura fungicides (b20)" (FRAC code 20) are proposed to affect cell division. Examples include pencycuron.

[0061] Quinone inside inhibitor (QiI) fungicides (b21) (FRAC code 21) inhibit complex III of fungal mitochondrial respiration by affecting ubiquinone reductase. The reduction of ubiquinone is prevented at the "quinone inside" (Qi) site of the cytochrome bc1 complex present in the inner mitochondrial membrane of fungi. By inhibiting mitochondrial respiration, they prevent normal growth and development of fungi. Quinone inside inhibitor fungicides include cyanoimidazoles, sulfamoyl-triazoles, and picolinamide fungicides. Cyanoimidazoles include cyazofamid. Sulfamoyl-triazoles include amisulbrom. Picolinamides include fenpicoxamide, florylpicoxamide, and methallylpicoxamide.

[0062] "Benzamide and thiazolecarboxamide fungicides (b22)" (FRAC code 22) inhibit mitosis by binding to β-tubulin and disrupting microtubule assembly. Inhibition of microtubule assembly can disrupt cell division, intracellular transport, and cellular structure. Benzamides include toluamides such as zoxamide. Thiazolecarboxamides include ethylaminothiazolecarboxamides such as ethaboxam.

[0063] "Enopyranuronic acid antibiotic fungicides (b23)" (FRAC code 23) are those that inhibit fungal growth by affecting protein biosynthesis. Examples include blasticidin-S.

[0064] "Hexopyranosyl antibiotic fungicides (b24)" (FRAC code 24) are those that inhibit fungal growth by affecting phospholipid biosynthesis. Examples include kasugamycin.

[0065] "Glucopyranosyl antibiotics: protein synthesis fungicides (b25)" (FRAC code 25) are those that inhibit fungal growth by affecting protein biosynthesis. Examples include streptomycin.

[0066] "Glucopyranosyl antibiotic fungicides (b26)" (FRAC code U18, formerly FRAC code 26, reclassified as U18) are proposed to inhibit trehalase and inositol biosynthesis. Examples include validamycin.

[0067] "Cyanoacetamide-oxime fungicides (b27)" (FRAC code 27) includes cymoxanil.

[0068] "Carbamate fungicides (b28)" (FRAC code 28) are considered multisite inhibitors of fungal growth. They are proposed to disrupt the synthesis of fatty acids in the cell membrane and subsequently disrupt the permeability of the cell membrane. Iodocarb, propamacarb, and prothiocarb are examples of this class of fungicides.

[0069] "Oxidative phosphorylation uncoupling fungicides (b29)" (FRAC code 29) inhibit fungal respiration by blocking oxidative phosphorylation. Inhibiting respiration prevents normal growth and development of fungi. This class includes dinitrophenyl crotonates such as binapacryl, meptyldinocap, and dinocap, and 2,6-dinitroanilines such as fluazinam.

[0070] "Organotin fungicides (b30)" (FRAC code 30) inhibit adenosine triphosphate (ATP) synthesis in the oxidative phosphorylation pathway. Examples include fentin acetate, fentin chloride, and fentin hydroxide.

[0071] "Carboxylic acid fungicides (b31)" (FRAC code 31) inhibit fungal growth by acting on deoxyribonucleic acid (DNA) topoisomerase type II (gyrase). Examples include oxolinic acid.

[0072] "Heteroaromatic fungicides (b32)" (FRAC code 32) are proposed for affecting DNA / ribonucleic acid (RNA) synthesis. Heteroaromatic fungicides include isoxazoles and isothiazolones. Isoxazoles include hymexazole and isothiazolones include octhilinone.

[0073] "Phosphonate fungicides (b33)" (FRAC code P07, formerly FRAC code 33, reclassified to P07) includes phosphorous acid and its various salts (including fosetylaluminium).

[0074] "Phthalamic acid fungicides (b34)" (FRAC code 34) includes tecloftalam.

[0075] "Benzotriazine fungicides (b35)" (FRAC code 35) includes triazoxide.

[0076] "Benzenesulfonamide fungicides (b36)" (FRAC code 36) includes flusulfamide.

[0077] "Pyridazinone fungicides (b37)" (FRAC code 37) includes diclomedine.

[0078] "Thiophene-carboxamide fungicides (b38)" (FRAC code 38) are proposed to affect ATP production. Examples include silthiofam.

[0079] "Complex I NADH oxidoreductase inhibitor fungicides (b39)" (FRAC code 39) inhibit electron transport in mitochondria and include pyrimidine amines such as diflumetrim, pyrazole-5-carboxamides such as tolfenpyrad, and quinazolines such as fenazaquin.

[0080] "Carboxylic acid amide (CAA) fungicides (b40)" (FRAC code 40) inhibit cellulose synthetase, preventing the growth of and killing target fungi. Carboxylic acid amide fungicides include cinnamic acid amide, carbamic acid valinamide, and mandelic acid amide fungicides. Cinnamic acid amides include dimethomorph, flumorph, and pyrimorph. Carbamic acid valinamides include benthiavalicarb, benthiavalicarb-isopropyl, iprovalicarb, tolprocarb, and valifenalate (also known as valifenal). Mandelic acid amides include mandipropamide, N-[2-[4-[[3-(4-chlorophenyl)-2-propyn-1-yl]oxy]-3-methoxyphenyl]ethyl]-3-methyl-2-[(methylsulfonyl)amino]butanamide, and N-[2-[4-[[3-(4-chlorophenyl)-2-propyn-1-yl]oxy]-3-methoxyphenyl]ethyl]-3-methyl-2-[(ethylsulfonyl)amino]butanamide.

[0081] "Tetracycline antibiotic fungicides (b41)" (FRAC code 41) are those that inhibit the growth of fungi by affecting protein synthesis. Examples include oxytetracycline.

[0082] "Thiocarbamate fungicides (b42)" (FRAC code M12, formerly FRAC code 42, reclassified to M12) includes metasulfocarb.

[0083] "Benzamide fungicides (b43)" (FRAC code 43) inhibit fungal growth by delocalizing spectrin-like proteins. Examples include pyridinylmethylbenzamides such as fluopicolide and fluopimomide.

[0084] "Microbial fungicides (b44)" (FRAC code BM02, formerly FRAC code 44, reclassified as BM02) destroy the cell membrane of fungal pathogens. Microbial fungicides include Bacillus species, such as Bacillus amyloliquefaciens strains AP-136, AP-188, AP-218, AP-219, AP-295, QST713, FZB24, F727, MB1600, D747, FCC1256 (deposited under ATCC Designation No. PTA-122162 and disclosed in PCT / US2019 / 053424), and TJ100 (also referred to as strain 1 BE; known from EP2962568), and the fungicidal lipopeptides they produce.

[0085] "Quinone outside inhibitor, stigmatellin binding (QoSI) fungicides (b45)" (FRAC code 45) inhibit complex III mitochondrial respiration in fungi by affecting ubiquinone reductase at the "quinone outside" (Qo) site, the stigmatellin-binding subsite, of the cytochrome bc1 complex. Inhibition of mitochondrial respiration prevents normal growth and development of fungi. QoSI fungicides include triazolo-pyrimidylamines such as ametocladine.

[0086] "Plant extract fungicides (b46)" (FRAC code 46) cause cell membrane disruption. Plant extract fungicides include terpene hydrocarbons, terpene alcohols and terpene phenols, such as extracts from Melaleuca alternifolia (tea tree), and vegetable oils (mixtures), such as eugenol, geraniol, and thymol.

[0087] "Cyanoacrylate fungicides (b47)" (FRAC code 47) bind to the myosin motor domain and affect motor activity and actin assembly. Cyanoacrylates include fungicides such as Fenamacryl.

[0088] "Polyene fungicides (b48)" (FRAC code 48) bind to ergosterol, the major membrane sterol, causing destruction of fungal cell membranes. Examples include natamycin (pimaricin).

[0089] "Oxysterol-binding protein inhibitor (OSBPI) fungicides (b49)" (FRAC code 49) bind to oxysterol-binding proteins of oomycetes and inhibit zoospore release, zoospore motility, and sporangial germination. Oxysterol-binding fungicides include piperidinyl-thiazole-isoxazolines such as oxathiapiprolin and fluoxapiprolin.

[0090] "Aryl-phenyl-ketone fungicides (b50)" (FRAC code 50, formerly FRAC code U8, reclassified as 50) inhibit the growth of fungal hyphae. Aryl phenyl ketone fungicides include benzophenones such as metrafenone, and benzoylpyridines such as pyriophenone.

[0091] "Host plant defense induction fungicides (b51)" induce the defense mechanisms of the host plant. Host plant defense induction fungicides include benzothiadiazoles (FRAC code P01), benzisothiazoles (FRAC code P02), thiadiazolecarboxamides (FRAC code P03), polysaccharides (FRAC code P04), plant extracts (FRAC code P05), microorganisms (FRAC code P06), and phosphonate fungicides (FRAC code P07, see (b33) above). Benzisothiazoles include acibenzolar-S-methyl. Benzisothiazoles include probenazole. Thiadiazolecarboxamides include tiadinil and isotianil. Polysaccharides include laminarin. The plant extracts include extracts from Reynoutria sachalinensis (giant knotweed). The microorganisms include cell walls of Bacillus mycoides isolate J and Saccharomyces cerevisiae strain LAS117.

[0092] "Multi-site active fungicides (b52)" are fungicides that inhibit fungal growth through multiple sites of action and have contact / preventive activity. Multi-site active fungicides include copper fungicides (FRAC code M01), sulfur fungicides (FRAC code M02), dithiocarbamate fungicides (FRAC code M03), phthalimide fungicides (FRAC code M04), chloronitrile fungicides (FRAC code M05), sulfamide fungicides (FRAC code M06), multi-site contact guanidine fungicides (FRAC code M07), triazine fungicides (FRAC code M08), quinone fungicides (FRAC code M09), quinoxaline fungicides (FRAC code M10), maleimide fungicides (FRAC code M11) and thiocarbamate (FRAC code M12, see (b42) above) fungicides. Copper fungicides are typically inorganic compounds containing copper in the copper(II) oxidation state; examples include copper oxychloride, copper sulfate, and copper hydroxide (including compositions such as Bordeaux's mixture (tribasic copper sulfate)). Sulfur fungicides are inorganic chemicals containing rings or chains of sulfur atoms; examples include elemental sulfur. Dithiocarbamate fungicides are fungicides containing a dithiocarbamate molecular moiety; examples include ferbam, mancozeb, maneb, metiram, propineb, thiram, zinc thiazole, zineb, and ziram. Phthalimide fungicides contain a phthalimide molecular moiety; examples include folpet, captan, and captafol. Chloronitrile fungicides contain aromatic rings substituted with chloro and cyano; examples include chlorothalonil. Sulfamide fungicides include dichlofluanid and trifluanid. Multi-site contact guanidine fungicides include guazatine, iminoctadine albesilate, and iminoctadine triacetate. Triazine fungicides include anilazine. Quinone fungicides include dithianon. Quinoxaline fungicides include quinomethionate (also known as thinomethionate). Maleimide fungicides include fluoroimide.

[0093] "Biological products with multiple mechanisms of action (b53)" include agents of biological origin that exhibit multiple mechanisms of action without evidence of a dominant mechanism of action. This class of fungicides includes polypeptide (lectin), phenolic, sesquiterpene, tritepenoid and coumarin fungicides (FRAC code BMO1), e.g., extracts from cotyledons of lupine plantlets. This class also includes microbial fungicides (FRAC code BMO2, see above (b44)).

[0094] "Fungicides other than those of components (a1) and (a2) and components (b1) to (b53); (b54)" includes certain fungicides whose mechanism of action may be unknown. These include (b54.1) "phenyl-acetamide fungicides" (FRAC code U06), (b54.2) "guanidine fungicides" (FRAC code U12), (b54.3) "thiazolidine fungicides" (FRAC code U13), (b54.4) "pyrimidinone-hydrazone fungicides" (FRAC code U14), (b54.5) "4-quinolyl acetate fungicides" (FRAC code U16), (b54.6) "tetrazolyl oxime fungicides" (FRAC code U17), and "glucopyranosyl antibiotic fungicides" (FRAC code U18, see (b26) above). Phenylacetamides include cyflufenamid. Guanidines include dodine. Thiazolidines include fluthianil. Pyrimidinone-hydrazones include ferimzone. 4-Quinolyl acetates include tebufloquine. Tetrazolyl oximes include picarbutrazox.

[0095] The (b54) class also includes bethoxadin, diclobenthiazox (tentative name, registration number 957144-77-3), dipimethitron (tentative name, registration number 16114-35-5), flometoquin, neoasozin (iron methanearsonate), pyrrolnitrin, tolnifanide (registration number 304911-98-6), N'-[4-[4-chloro-3-(trifluoromethyl)phenoxy]-2,5-dimethyl-phenyl]-N-ethyl-N-methylmethanimidamide, 5-fluoro-2-[(4-fluorophenyl)methoxy]-4-pyrimidinamine, and 4-fluoro-phenyl-N-[1-[[ [1-(4-cyanophenyl)ethyl]sulfonyl]methyl]propyl]carbamate, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxyethoxy)-3-pyridinyl]-N-ethyl-N-methyl-methanimidamide, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxyethoxy]-3-pyridinyl]-N-ethyl-N-methyl-methanimidamide, and N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxyethoxy]-3-pyridinyl]-N-ethyl-N-methyl-methanimidamide.

[0096] Additional "fungicidal agents other than those of classes (1) to (54)" for which the mechanism of action may be unknown or cannot yet be classified include fungicidal compounds selected from components (b54.8) to (b54.14) below.

[0097] Ingredient (54.9) relates to 3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenylpyridazine (provisional name pyridaclomethyl, registration number 1358061-55-8), which is believed to be a tubulin polymerization promoter and provides antifungal activity against fungal species belonging to the Ascomycota and Basidiomycota phyla.

[0098] Ingredient (54.10) relates to (4-phenoxyphenyl)methyl 2-amino-6-methyl-pyridine-3-carboxylate (provisional name: aminopyrifen, registration number 1531626-08-0), which is thought to inhibit the GWT-1 protein in glycosylphosphatidylinositol-anchor biosynthesis in Neurospora crassa.

[0099] The component (b54.11) is given by the formula b54.11 [ka] [In the formula, R b1 and R b3 are each independently a halogen; R b2 is H, halogen, C1-C3 alkyl, C1-C3 haloalkyl, or C3-C6 cycloalkyl] The present invention relates to the compound

[0100] Examples of compounds of formula b54.11 include (b54.11a) methyl N-[[5-[1-(2,6-difluoro-4-formylphenyl)-1H-pyrazol-3-yl]-2-methylphenyl]methyl]carbamate, (b54.11b) methyl N-[[5-[1-(4-cyclopropyl-2,6-dichlorophenyl)-1H-pyrazol-3-yl]-2-methylphenyl]methyl]carbamate, (b54.11c) methyl N-[[5-[1-(4-chloro-2,6-difluorophenyl)-1H-pyrazol-3-yl]-2-methylphenyl]methyl]carbamate, (b 54.11d) methyl N-[[5-[1-(4-cyclopropyl-2,6-difluorophenyl)-1H-pyrazol-3-yl]-2-methylphenyl]methyl]carbamate, (b54.11e) methyl N-[[5-[1-[2,6-difluoro-4-(1-methylethyl)phenyl]-1H-pyrazol-3-yl]-2-methylphenyl]methyl]carbamate, and (b54.11f) methyl N-[[5-[1-[2,6-difluoro-4-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl]-2-methylphenyl]methyl]carbamate. Compounds of formula b54.11, their use as fungicides and methods for their preparation are generally known, see, for example, PCT Patent Publications WO 2008 / 124092, WO 2014 / 066120 and WO 2020 / 097012.

[0101] The component (b54.12) is the formula b54.12 [ka] [In the formula, R b4 teeth, [ka] and R b6 is a C2-C4 cyanoalkyl, a C2-C4 alkoxycarbonyl, or a C2-C4 haloalkylaminocarbonyl; L is CH2 or CH2O, the atom on the right is connected to the phenyl ring in formula b54.12, and R b5 teeth, [ka] is] The present invention relates to the compound

[0102] Examples of compounds of formula b54.12 include (b54.12a) N-(2,2,2-trifluoroethyl)-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-4-oxazolecarboxamide, (b54.12b) ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenoxy]methyl]-1H-pyrazole-4-carboxyle (b54.12c) 3-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-1H-pyrazole-1-acetonitrile, and (b54.12d) N-(2,2,2-trifluoroethyl)-5-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-1,2,4-oxadiazole-3-carboxamide. Compounds of formula b54.12, their use as fungicides and methods for their preparation are generally known; see, for example, PCT Patent Publication WO 2020 / 056090.

[0103] The component (b54.13) is the formula b54.13 [ka] [In the formula, R b7 , R b8 , and R b9 are each independently H, halogen, or cyano; R b10 and R b11 are each independently H, halogen, C1-C3 alkyl, or C1-C3 methoxy. The present invention relates to the compound

[0104] Examples of compounds of formula b54.13 include: (b54.13a) 4-(2-chloro-4-fluorophenyl)-N-(2-fluoro-4-methyl-6-nitrophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (b54.13b) 4-(2-chloro-4-fluorophenyl)-N-(2-fluoro-6-nitrophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (b54.13c) 3,5-difluoro-4-[5-[(4-methoxy-2-nitrophenyl)amino]-1,3-dimethyl-1H-pyrazol-4-yl] -benzonitrile, (b54.13d) N-(2-chloro-4-fluoro-6-nitrophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (b54.13e) 4-(2-chloro-4,6-difluorophenyl)-1,3-dimethyl-N-(2-nitrophenyl)-1H-pyrazol-5-amine, and (b54.13f) 4-(2-chloro-4,6-difluorophenyl)-1,3-dimethyl-N-(4-methyl-2-nitrophenyl)-1H-pyrazol-5-amine. Compounds of formula b54.13, their use as fungicides, and methods for their preparation are generally known; see, for example, PCT Patent Publication WO 2020051402.

[0105] Ingredient (54.14) relates to N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide (generic name flufenoxadiazam, registration number 1839120-27-2), which is believed to be a class II histone deacetylase (HDAC) inhibitor.

[0106] Embodiments of the present disclosure may be combined in any manner, provided that the combination results in the compositions and methods claimed herein.

[0107] Embodiments of the invention as described in the Summary of the Invention include those described below. In the embodiments below, the recited formulas include stereoisomers, N-oxides, and salts thereof, and references to "compounds of Formula I" or "compounds of Formula II" include the definitions of the substituents defined in the Summary of the Invention, unless further defined in the embodiments.

[0108] Embodiment A1. The composition described in the Summary of the Invention, wherein the SDHI is: (a1-a) phenylbenzamide, benodanil, flutolanil, mepronil, phenyloxoethylthiophenamide, isofetamide, fluopyram, furancarboxamide, fenfuram, oxathiincarboxamide, carboxin and oxycarboxin, thiazolecarboxamide, thifluzamide, pyrazole-4-carboxamide, benzovindiflupyr, bixafen, fluveneteram, fluindapyr, fluxapyroxad, furametpyr, inpirfluxam, isopyrazam, Penflufen, penthiopyrad, sedaxane, N-[2-(2,4-dichlorophenyl)-2-methoxy-1-methylethyl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, N-cyclopropyl-N-benzyl-pyrazolecarboxamide, isoflucipram, N-methoxy-(phenyl-ethyl)-pyrazolecarboxamide, pydiflumetofen, pyridinecarboxamide, boscalid, pyrazinecarboxamide fungicides, and pyraziflumid, and (a1-b) Formula (I): [ka] [In the formula, R 1 , R 2 , R 3 and R 4 are each independently H, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, or C3-C6 halocycloalkyl; R 5 and R 7 are each independently H, C1-C4 alkyl, or C1-C4 haloalkyl; R 6 is C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, or C1-C4 haloalkylthio, R 8 is halo, -OH, -SH, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, or C1-C4 haloalkylthio; n is 0 to 3. and aminoindanamides having the structure (a1-c) Combinations of these A composition selected from:

[0109] Embodiment A2. The SDHI has formula (I): [ka] [In the formula, R 1 , R 2 , R 3 and R 4 are each independently H, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, or C3-C6 halocycloalkyl; R 5 and R 7 are each independently H, C1-C4 alkyl, or C1-C4 haloalkyl; R 6 is C1-C4 alkyl, C1-C4 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, or C1-C4 haloalkylthio, R 8 is halo, -OH, -SH, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C1-C4 alkylthio, or C1-C4 haloalkylthio; n is 0 to 3. The composition of embodiment A1, wherein the aminoindan amide has the structure:

[0110] Embodiment A3. R 1 , R 2 , R 4 and R 6 are each independently C1-C4 alkyl, R 3 is H, C1-C4 alkyl or C1-C4 haloalkyl; R 5 and R 7 are each independently H, C1-C4 alkyl, or C1-C4 haloalkyl; R 8 is halo, C1-C4 alkyl or C1-C4 haloalkyl; The composition of embodiment A2, wherein n is 0-3.

[0111] Embodiment A4.R 1 , R 2 , R 4 and R 6 The composition of embodiment A2, wherein each is methyl.

[0112] Embodiment A5.R 3 The composition of embodiment A2, wherein

[0113] Embodiment A6.R 7 The composition of embodiment A2, wherein is methyl, difluoromethyl, or trifluoromethyl.

[0114] Embodiment A7.R 5 The composition of embodiment A2, wherein is H or methyl.

[0115] Embodiment A8. The composition of embodiment A2, wherein n is 1-3.

[0116] Embodiment A9.R 8 The composition of embodiment A2, wherein is halo.

[0117] Embodiment A10.R 8 The composition of embodiment A2, wherein

[0118] Embodiment A11. The aminoindan amide of Formula (I) is [ka] The composition of embodiment A2, wherein

[0119] Embodiment A12. The aminoindanamide of Formula (I) is (fluindapyr) [ka] The composition of embodiment A2 or A11, wherein

[0120] Embodiment A13The composition of embodiment A2 wherein a.n is 0.

[0121] The composition of embodiment A2 wherein embodiment A13b.n is 1.

[0122] Embodiment A14a. The SDHI is selected from the group consisting of phenylbenzamide, benodanil, flutolanil, mepronil, phenyloxoethylthiophenamide, isofetamide, pyridinylethylbenzamide, fluopyram, furancarboxamide, fenfuram, oxathiincarboxamide, carboxin and oxycarboxin, thiazolecarboxamide, thifluzamide, pyrazole-4-carboxamide, benzovindiflupyr, bixafen, fluveneteram, fluindapyr, fluxapyroxad, furametpyr, inpirfluxam, isopyramide The composition of embodiment A1, wherein the fungicide is selected from azam, penflufen, penthiopyrad, sedaxane, N-[2-(2,4-dichlorophenyl)-2-methoxy-1-methylethyl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, N-cyclopropyl-N-benzyl-pyrazolecarboxamide, isoflucipram, N-methoxy-(phenyl-ethyl)-pyrazolecarboxamide, pydiflumetofen, pyridinecarboxamide, boscalid, pyrazinecarboxamide fungicides, and pyraziflumid.

[0123] Embodiment A14b. The composition of embodiment A14a wherein the SDHI is selected from benzovindiflupyr, bixafen, fluindapyr, fluxapyroxad, inpirfluxam, isoflucipram, pydiflumetofen, and boscalid.

[0124] Embodiment A14c. The composition of embodiment A14b wherein the SDHI is selected from benzovindiflupyr, bixafen, fluindapyr, fluxapyroxad, and boscalid.

[0125] Embodiment A14d. The composition of embodiment A14c wherein the SDHI is selected from benzovindiflupyr, fluindapyr, and fluxapyroxad.

[0126] Embodiment A15. The composition of embodiment A14a wherein the SDHI is selected from phenylbenzamides.

[0127] Embodiment A16. The composition of embodiment A14a, wherein the SDHI is benodanil.

[0128] Embodiment A17 The composition of embodiment A14a wherein the SDHI is flutolanil.

[0129] Embodiment A18. The composition of embodiment A14a, wherein the SDHI is mepronil.

[0130] Embodiment A19. The composition of Embodiment A14a wherein the SDHI is selected from phenyloxoethylthiophenamides.

[0131] Embodiment A20. The composition of embodiment A14a, wherein the SDHI is isofetamide.

[0132] Embodiment A21 The composition of embodiment A14a wherein the SDHI is selected from pyridinylethylbenzamides.

[0133] Embodiment A22 The composition of embodiment A14a, wherein the SDHI is fluopyram.

[0134] Embodiment A23 The composition of embodiment A14a wherein the SDHI is selected from furancarboxamides.

[0135] Embodiment A24 The composition of embodiment A14a, wherein the SDHI is fenfuram.

[0136] Embodiment A25. The composition of embodiment A14a wherein the SDHI is selected from oxathiine carboxamides.

[0137] Embodiment A26 The composition of embodiment A14a, wherein the SDHI is carboxin.

[0138] Embodiment A27 The composition of embodiment A14a, wherein the SDHI is oxycarboxin.

[0139] Embodiment A28 The composition of embodiment A14a wherein the SDHI is selected from thiazolecarboxamides.

[0140] Embodiment A29. The composition of embodiment A14a, wherein the SDHI is thifluzamide.

[0141] Embodiment A30. The composition of embodiment A14a wherein the SDHI is selected from pyrazole-4-carboxamides.

[0142] Embodiment A31 The composition of embodiment A14a wherein the SDHI is benzovindiflupyr.

[0143] Embodiment A32. The composition of embodiment A14a, wherein the SDHI is bixafen.

[0144] Embodiment A33. The composition of embodiment A14a, wherein the SDHI is fulveneteram.

[0145] Embodiment A34 The composition of embodiment A14a, wherein the SDHI is fluindapyr.

[0146] Embodiment A35 The composition of embodiment A14a wherein the SDHI is fluxapyroxad.

[0147] Embodiment A36 The composition of embodiment A14a, wherein the SDHI is furametpyr.

[0148] Embodiment A37. The composition of embodiment A14a, wherein the SDHI is inpirfluxam.

[0149] Embodiment A38 The composition of embodiment A14a, wherein the SDHI is isopyrazam.

[0150] Embodiment A39 The composition of embodiment A14a, wherein the SDHI is penflufen.

[0151] Embodiment A40. The composition of embodiment A14a, wherein the SDHI is penthiopyrad.

[0152] Embodiment A41 The composition of embodiment A14a wherein the SDHI is sedaxane.

[0153] Embodiment A42 The composition of embodiment A14a wherein the SDHI is N-[2-(2,4-dichlorophenyl)-2-methoxy-1-methylethyl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide.

[0154] Embodiment A43. The composition of embodiment A14a wherein the SDHI is selected from N-cyclopropyl-N-benzyl-pyrazolecarboxamides.

[0155] Embodiment A44. The composition of embodiment A14a, wherein the SDHI is isoflucipram.

[0156] Embodiment A45. The composition of embodiment A14a wherein the SDHI is selected from N-methoxy-(phenyl-ethyl)-pyrazolecarboxamides.

[0157] Embodiment A46. The composition of embodiment A14a, wherein the SDHI is pydiflumetofen.

[0158] Embodiment A47. The composition of embodiment A14a wherein the SDHI is selected from pyridine carboxamides.

[0159] Embodiment A48. The composition of embodiment A14a, wherein the SDHI is boscalid.

[0160] Embodiment A49. The composition of embodiment A14a wherein the SDHI is selected from pyridinecarboxamide fungicides.

[0161] Embodiment A50. The composition of embodiment A14a, wherein the SDHI is pyraziflumid.

[0162] Embodiment B1. The composition described in the Summary of the Invention, wherein the picolinamide is: (a2-a) fenpicoxamide, florylpicoxamide, [(1S,2S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, [(1S,2S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl](2S)-2-[[3-(acetoxymethoxy)-4-methoxy-pyridine-2-carbonyl]amino]propanoate, and [(1S,2S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl](2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, (a2-b) methallyl picoxamide, (a2-c) Formula (II): [ka] [In the formula, R 9 is H or alkyl and zero, one, or more R 19 is replaced by R 10 and R 11 is R 19 and R is independently selected from C2-C6 alkyl, C3-C6 cycloalkyl, aryl, or heteroaryl, each optionally substituted with 0, 1, or more selected from 10 and R 11 together form zero, one, or more R 19 forming a 3- to 6-membered saturated or partially saturated carbocyclic or heterocyclic ring optionally substituted with R 12 is aryl or heteroaryl, each of which may contain zero, one, or more R 19 and optionally substituted with R 13 are H or alkyl, each of which may contain zero, one, or more R 19 and optionally substituted with R 14 is H or C(O)R 16 and R 15 is H,C(O)R 16 or Q, Q is [ka] (Wherein, Z is N or N + →O - and W is O or S; R 16 is alkoxy or benzyloxy, each of which may contain zero, one, or more R 19 and optionally substituted with R 17 is H, alkoxy, or halo, each of which may contain zero, one, or more R 19 and optionally substituted with R 18 is H, -C(O)R 20 , or -CH2OC(O)R 20 Because, R 19 is H, alkyl, aryl, acyl, halo, alkenyl, alkynyl, alkoxy, cyano, or heterocyclyl, each of which may be zero, one, or more R 21 and optionally substituted with R 20 is alkyl, alkoxy, or aryl, each of which may contain zero, one, or more R 19 and optionally substituted with R 21 is H, alkyl, aryl, acyl, halo, alkenyl, alkoxy, or heterocyclyl). Picolinamide having the structure (a2-d) Combinations of these A composition selected from:

[0163] Embodiment B2. The picolinamide is of formula (II) [ka] [In the formula, R 9 is H or alkyl and zero, one, or more R 19 is replaced by R 10 and R 11 is zero, one, or more R 19 or R 10 and R 11 together form zero, one, or more R 19 forming a 3- to 6-membered saturated or partially saturated carbocyclic or heterocyclic ring optionally substituted with R 12 is aryl or heteroaryl, each of which may contain zero, one, or more R 19 and optionally substituted with R 13 are H or alkyl, each of which may contain zero, one, or more R 19 and optionally substituted with R 14 is H or C(O)R 16 and R 15 is H,C(O)R 16 , or Q, Q is [ka] (Wherein, Z is N or N + →O - and W is O or S; R 16 is alkoxy or benzyloxy, each of which may contain zero, one, or more R 19 and optionally substituted with R 17 is H, alkoxy, or halo, each of which may contain zero, one, or more R 19 and optionally substituted with R 18 is H, -C(O)R 20 , or -CH2OC(O)R 20and R 19 is H, alkyl, aryl, acyl, halo, alkenyl, alkynyl, alkoxy, cyano, or heterocyclyl, each of which may be zero, one, or more R 21 and optionally substituted with R 20 is alkyl, alkoxy, or aryl, each of which may contain zero, one, or more R 19 and optionally substituted with R 21 is selected from H, alkyl, aryl, acyl, halo, alkenyl, alkoxy, or heterocyclyl). The composition of embodiment B1, wherein the picolinamide has the structure:

[0164] Embodiment B3.R 14 is H and R 15 The composition of embodiment B2, wherein

[0165] Embodiment B4. The composition of Embodiment B2 wherein Z is N.

[0166] Embodiment B5. The composition of Embodiment B2 wherein W is O.

[0167] Embodiment B6.R 17 The composition of embodiment B2, wherein is alkoxy.

[0168] Embodiment B7.R 18 The composition of embodiment B2, wherein is H.

[0169] Embodiment B8.R 9 and R 13 is independently selected from H or alkyl; R 10 and R 11 are independently selected from C2-C6 alkyl, or together, each optionally selected from zero, one, or more R 19 forming a 3- to 6-membered saturated carbocyclic ring substituted with R 12 optionally zero, one, or more R19 The composition of embodiment B2 wherein N is aryl substituted with .

[0170] Embodiment B9. The composition of embodiment B1, wherein the picolinamide is selected from fenpicoxamide, florylpicoxamide, [(1S,2S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, [(1S,2S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl](2S)-2-[[3-(acetoxymethoxy)-4-methoxy-pyridine-2-carbonyl]amino]propanoate, and [(1S,2S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl](2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate.

[0171] Embodiment B10. The composition of embodiment B9, wherein the picolinamide is fenpicoxamide.

[0172] Embodiment B11. The composition of embodiment B9, wherein the picolinamide is florylpicoxamide.

[0173] Embodiment B12. The composition of embodiment B9 wherein the picolinamide is [(1S,2S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate.

[0174] Embodiment B13. The composition of embodiment B9 wherein the picolinamide is [(1S,2S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl](2S)-2-[[3-(acetoxymethoxy)-4-methoxy-pyridine-2-carbonyl]amino]propanoate.

[0175] Embodiment B14. The composition of embodiment B9 wherein the picolinamide is [(1S,2S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl](2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate.

[0176] Embodiment B15. The composition of embodiment B1 wherein the picolinamide is methallyl picoxamide.

[0177] The embodiments of the present invention, including the above embodiments and any other embodiments described herein, can be combined in any manner, and the descriptions of variables in the embodiments relate not only to compositions comprising (a1) a succinate dehydrogenase inhibitor (SDHI) and (a2) a picolinamide, but also to compositions comprising (a1) a succinate dehydrogenase inhibitor (SDHI) and (a2) a picolinamide with at least one invertebrate pest control compound or agent. Furthermore, embodiments of the present invention, including the above embodiments B1-B15 and any other embodiments described herein, and any combination thereof, relate to methods of the present invention. Accordingly, of note as a further embodiment are compositions disclosed above comprising (a1) a succinate dehydrogenase inhibitor (SDHI) and (a2) a picolinamide, and at least one invertebrate pest control compound or agent.

[0178] Embodiment C1. The composition described in the Summary of the Invention further comprising at least one component (b).

[0179] Embodiment C2. The composition comprises: (b1) methyl benzimidazole carbamate (MBC) fungicide, (b2) dicarboximide fungicides, (b3) demethylation inhibitor (DMI) fungicides; (b4) phenylamide (PA) fungicides, (b5) amine / morpholine fungicides, (b6) phospholipid biosynthesis inhibitor fungicides, (b7) an additional succinate dehydrogenase inhibitor (SDHI) fungicide; (b8) hydroxy(2-amino-)pyrimidine fungicides, (b9) Anilinopyrimidine (AP) fungicides, (b10) N-phenylcarbamate fungicides, (b11) Quinone Outside Inhibitor (QoI) fungicides, (b12) phenylpyrrole (PP) fungicides, (b13) azanaphthalene fungicides, (b14) cell peroxidation inhibitors fungicides, (b15) melanin biosynthesis inhibitor-reductase (MBI-R) fungicides; (b16a) melanin biosynthesis inhibitor-dehydratase (MBI-D) fungicides, (b16b) Melanin biosynthesis inhibitor-polyketide synthase (MBI-P) fungicides, (b17) ketoreductase inhibitor (KRI) fungicides, (b18) squalene-epoxidase inhibitor fungicides, (b19) polyoxin fungicides, (b20) phenylurea fungicides, (b21) quinone inside inhibitor (QiI) fungicides, (b22) benzamide and thiazolecarboxamide fungicides, (b23) enopyranuronic acid antibiotic fungicides, (b24) hexopyranosyl antibiotic fungicides, (b25) glucopyranosyl antibiotics: protein synthesis fungicides, (b26) glucopyranosyl antibiotic fungicides, (b27) cyanoacetamide oxime fungicides, (b28) carbamate fungicides, (b29) oxidative phosphorylation uncoupling fungicides, (b30) organotin fungicides, (b31) carboxylic acid fungicides, (b32) heterocyclic aromatic compound fungicides, (b33) phosphonate fungicides, (b34) phthalamic acid fungicides, (b35) benzotriazine fungicides, (b36) benzene-sulfonamide fungicides, (b37) pyridazinone fungicides, (b38) thiophene-carboxamide fungicides, (b39) Complex I NADH oxidoreductase inhibitor fungicide, (b40) carboxylic acid amide (CAA) fungicides, (b41) tetracycline antibiotic fungicides, (b42) thiocarbamate fungicides, (b43) benzamide fungicides, (b44) microbial fungicides, (b45) quinone outside inhibitor, stigmatellin binding (QoSI) fungicides, (b46) plant extract fungicides, (b47) cyanoacrylate fungicides, (b48) polyene fungicides, (b49) oxysterol binding protein inhibitor (OSBPI) fungicides, (b50) aryl-phenyl-ketone fungicides, (b51) host plant defense-inducing fungicides, (b52) multi-site active fungicides, (b53) Biological agents with multiple mechanisms of action; (b54) Fungicides other than the fungicides of component (a1), component (a2), and components (b1) to (b53), and Salts of compounds (b1) to (b54) The composition of embodiment C1, further comprising at least one component (b) selected from:

[0180] Embodiment C3. The composition of Embodiment C2 wherein component (b) comprises at least one fungicidal compound from each of two different groups selected from (b1) through (b54).

[0181] Embodiment C4. The composition of embodiment C1 wherein component (b) comprises at least one compound selected from (b1) a methyl benzimidazole carbamate fungicide, such as benomyl, carbendazim, fuberidazole thiabendazole, thiophanate, and thiophanate methyl.

[0182] Embodiment C5. The composition of Embodiment C1 wherein component (b) comprises (b2) at least one compound selected from dicarboximide fungicides such as chlozolinate, dimethachlon, iprodione, procymidone, and vinclozolin.

[0183] Embodiment C6. Component (b) is (b3) azaconazole, bitertanol, bromuconazole, buthiobate, cyproconazole, difenoconazole, diniconazole (including diniconazole-M), econazole, epoxiconazole, etaconazole, fenarimol, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imazalil, imibenconazole, ipconazole, ipfentrifluconazole, mefentrifluconazole, metconazole The composition of embodiment C1, comprising at least one compound selected from demethylation inhibitor fungicides such as benzophenone, myclobutanil, nuarimol, oxpoconazole, pefurazoate, penconazole, prochloraz, propiconazole, pyrifenox, pyrisoxazole, quinconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triarimol, triflumizole, triforine, triticonazole, uniconazole, and uniconazole-P.

[0184] Embodiment C7. The composition of embodiment C1 wherein component (b) comprises at least one compound selected from (b4) phenylamide fungicides such as benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M, ofurace, and oxadixyl.

[0185] Embodiment C8. The composition of embodiment C1 wherein component (b) comprises (b5) at least one compound selected from amine / morpholine fungicides such as aldimorph, dodemorph, fenpropidin, fenpropimorph, piperaline, spiroxamine, tridemorph, and trimorphamide.

[0186] Embodiment C9. The composition of embodiment C1 wherein component (b) comprises at least one compound selected from (b6) phospholipid biosynthesis inhibitor fungicides such as eifenphos, iprobenfos, isoprothiolane, and pyrazophos.

[0187] Embodiment C10. The composition of embodiment C1 wherein component (b) comprises at least one compound selected from (b7) succinate dehydrogenase inhibitor fungicides such as benodanil, benzovindiflupyr, bixafen, boscalid, carboxin, fenfuram, fluveneteram, fluindapyr, fluopyram, flutolanil, fluxapyroxad, furametpyr, inpirfluxam, isofetamide, isoflucipram, isopyrazam, mepronil, oxycarboxin, penflufen, penthiopyrad, pydiflumetofen, pyrapropoin, pyraziflumide, sedaxane, and thifluzamide.

[0188] Embodiment C11. The composition of Embodiment C1 wherein component (b) comprises at least one compound selected from (b8) hydroxy(2-amino-)pyrimidine fungicides, such as bupirimate, dimethylmol, and ethirimol.

[0189] Embodiment C12. The composition of Embodiment C1 wherein component (b) comprises at least one compound selected from (b9) an anilinopyrimidine fungicide, such as cyprodinil, mepanipyrim, and pyrimethanil.

[0190] Embodiment C13. The composition of Embodiment C1 wherein component (b) comprises at least one compound selected from (b10) N-phenylcarbamate fungicides, such as diethofencarb.

[0191] Embodiment C14. The composition of embodiment C1 wherein component (b) comprises at least one compound selected from (b11) a fungicidal quinone outside inhibitor fungicide, such as azoxystrobin, cumoxystrobin, dimoxystrobin, enoxastrobin, famoxadone, fenamidone, phenaminestrobin, flufenoxystrobin, fluoxastrobin, kresoxim-methyl, mandestrobin, metominostrobin, methyltetraprole, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyroxystrobin, pyribencarb, triclopyricarb, and trifloxystrobin.

[0192] Embodiment C15. The composition of Embodiment C1 wherein component (b) comprises at least one compound selected from (b12) phenylpyrrole fungicidal compounds, such as fenpiclonil and fludioxonil.

[0193] Embodiment C16. The composition of Embodiment C1 wherein component (b) comprises at least one compound selected from (b13) azanaphthalene fungicides, such as quinoxyfen and proquinazide.

[0194] Embodiment C17. The composition of embodiment C1 wherein component (b) comprises at least one compound selected from (b14) cellular peroxidation inhibitor fungicides such as biphenyl, chloroneb, dicloran, etridiazole, quintozene, tecnazene, and tolclofos-methyl.

[0195] Embodiment C18. The composition of embodiment C1 wherein component (b) comprises at least one compound selected from (b15) melanin biosynthesis inhibitor-reductase fungicides, such as phthalide, pyroquilon, and tricyclazole.

[0196] Embodiment C19a. The composition of embodiment C1 wherein component (b) comprises at least one compound selected from (b16a) melanin biosynthesis inhibitors such as carpropamid, diclocymet, and fenoxanil-dehydratase fungicides.

[0197] Embodiment C19b. The composition of Embodiment C1 wherein component (b) comprises at least one compound selected from (b16b) a melanin biosynthesis inhibitor-polyketide synthase fungicide, such as tolprocarb.

[0198] Embodiment C20. The composition of embodiment C1 wherein component (b) comprises at least one compound selected from (b17) ketoreductase inhibitor fungicides such as fenhexamid, fenpyrazamine, ipflufenoquin, and quinofumelin.

[0199] Embodiment 21. The composition of embodiment C1, wherein component (b) comprises at least one compound selected from (b18) squalene-epoxidase inhibitor fungicides, such as naftifine, pyributicarb, and terbinafine.

[0200] Embodiment C22. The composition of Embodiment C1 wherein component (b) comprises at least one compound selected from (b19) a polyoxin fungicide, such as a polyoxin.

[0201] Embodiment C23. The composition of Embodiment C1 wherein component (b) comprises at least one compound selected from (b20) a phenylurea fungicide, such as pencycuron.

[0202] Embodiment C24. The composition of embodiment C1 wherein component (b) comprises at least one compound selected from (b21) quinone inside inhibitor fungicides, such as amisulbrom, cyazofamid, fenpicoxamid, and florylpicoxamid.

[0203] Embodiment C24a. The composition of Embodiment C1 wherein component (b) comprises at least one compound selected from (b21) a quinone inside inhibitor fungicide, such as methallyl picoxamide.

[0204] Embodiment C25. The composition of Embodiment C1 wherein component (b) comprises at least one compound selected from (b22) benzamide and thiazolecarboxamide fungicides, such as ethaboxam and zoxamide.

[0205] Embodiment C26. The composition of Embodiment C1 wherein component (b) comprises at least one compound selected from (b23) enopyranuronic acid antibiotic fungicides, such as blasticidin-S.

[0206] Embodiment C27. The composition of Embodiment C1 wherein component (b) comprises at least one compound selected from (b24) a hexopyranosyl antibiotic fungicide, such as kasugamycin.

[0207] Embodiment C28. The composition of embodiment C1 wherein component (b) comprises at least one compound selected from (b25) glucopyranosyl antibiotics, such as streptomycin; protein synthetic fungicides.

[0208] Embodiment C29. The composition of embodiment C1 wherein component (b) comprises at least one compound selected from (b26) glucopyranosyl antibiotics, such as validamycin: trehalase and inositol biosynthesis fungicides.

[0209] Embodiment C30. The composition of Embodiment C1 wherein component (b) comprises at least one compound selected from (b27) a cyanoacetylamidoxime fungicide, such as cymoxanil.

[0210] Embodiment C31. The composition of Embodiment C1 wherein component (b) comprises at least one compound selected from (b28) carbamate fungicides, such as iodocarb, propamacarb, and prothiocarb.

[0211] Embodiment C32. The composition of Embodiment C1 wherein component (b) comprises at least one compound selected from (b29) oxidative phosphorylation uncoupling fungicides such as binapacryl, dinocap, fluazinam, and meptyldinocap.

[0212] Embodiment C33. The composition of Embodiment C1 wherein component (b) comprises at least one compound selected from (B30) organotin fungicides such as fentin acetate, fentin chloride, and fentin hydroxide.

[0213] Embodiment C34. The composition of Embodiment C1 wherein component (b) comprises at least one compound selected from (b31) a carboxylic acid fungicide, such as oxolinic acid.

[0214] Embodiment C35. The composition of Embodiment C1 wherein component (b) comprises at least one compound selected from (b32) hymexazole and heteroaromatic fungicides such as octhilinone.

[0215] Embodiment C36. The composition of Embodiment C1 wherein component (b) comprises at least one compound selected from (b33) phosphonate fungicides such as phosphorous acid and its various salts, including fosetyl aluminum.

[0216] Embodiment C37. The composition of Embodiment C1 wherein component (b) comprises at least one compound selected from (b34) a phthalate fungicide, such as tecloftalam.

[0217] Embodiment C38. The composition of Embodiment C1 wherein component (b) comprises at least one compound selected from (b35) a benzotriazine fungicide, such as triazoxide.

[0218] Embodiment C39. The composition of Embodiment C1 wherein component (b) comprises at least one compound selected from (b36) a benzenesulfonamide fungicide, such as flusulfamide.

[0219] Embodiment C40. The composition of Embodiment C1 wherein component (b) comprises at least one compound selected from (b37) a pyridazinone fungicide, such as diclomedine.

[0220] Embodiment C41. The composition of Embodiment C1 wherein component (b) comprises at least one compound selected from (b38) a thiophenecarboxamide fungicide, such as silthiofam.

[0221] Embodiment C42. The composition of embodiment C1 wherein component (b) comprises at least one compound selected from (b39) complex I NADH oxidoreductase inhibitor fungicides, such as diflumetrim, fenazaquin, and tolfenpyrad.

[0222] Embodiment C43. The composition of embodiment C1 wherein component (b) comprises at least one compound selected from (b40) carboxylic acid amide fungicides such as benthiavalicarb, benthiavalicarb-isopropyl, dimethomorph, flumorph, iprovalicarb, mandipropamid, pyrimorph, tolprocarb, and valifenalate.

[0223] Embodiment C44. The composition of Embodiment C1 wherein component (b) comprises at least one compound selected from (b41) a tetracycline antibiotic fungicide, such as oxytetracycline.

[0224] Embodiment C45. The composition of Embodiment C1 wherein component (b) comprises at least one compound selected from (b42) a thiocarbamate fungicide, such as metasulfocarb.

[0225] Embodiment C46. The composition of Embodiment C1 wherein component (b) comprises at least one compound selected from (b43) benzamide fungicides, such as fluopicolide and fluopimomide.

[0226] Embodiment C47. The composition of embodiment C1, wherein component (b) comprises at least one compound selected from (b44) microbial fungicides, such as Bacillus amyloliquefaciens strains AP-136, AP-188, AP-218, AP-219, AP-295, D747, F727, FCC1256, FZB24, FZB42, MB1600, QST713, RTI301, RTI472, TJ100 (also known as strain 1BE; known from EP 2 962 568 B1) and the fungicidal lipopeptides they produce.

[0227] Embodiment C48. The composition of Embodiment C1 wherein component (b) comprises at least one compound selected from (b45) a quinone outside inhibitor such as ametoclazine, a stigmatellin-binding fungicide.

[0228] Embodiment C49. The composition of Embodiment C1 wherein component (b) comprises at least one compound selected from (b46) plant extract fungicides such as eugenol, geraniol, and thymol.

[0229] Embodiment C50. The composition of Embodiment C1 wherein component (b) comprises at least one compound selected from (b47) cyanoacrylate fungicides, such as fenamacryl.

[0230] Embodiment C51. The composition of Embodiment C1 wherein component (b) comprises at least one compound selected from (b48) polyene fungicides, such as natamycin.

[0231] Embodiment C52. The composition of embodiment C1 wherein component (b) comprises at least one compound selected from (b49) oxysterol binding protein inhibitor fungicides, such as oxathiapiprolin and fluoxapiprolin.

[0232] Embodiment C53. The composition of Embodiment C1 wherein component (b) comprises at least one compound selected from (b50) aryl-phenyl-ketone fungicides, such as metrafenone and pyriophenone.

[0233] Embodiment C54. The composition of embodiment C1, wherein component (b) comprises at least one compound selected from (b51) acibenzolar-S-methyl, probenazole, tiadinil, isotianil, laminarin, extracts from Reynoutria sachalinensis and Bacillus mycoides isolate J, and host plant defense-inducing fungicides such as the cell wall of Saccharomyces cerevisiae strain LAS117.

[0234] Embodiment C55. The composition of embodiment C1 wherein component (b) comprises (b52) at least one compound selected from copper oxychloride, copper sulfate, copper hydroxide, Bordeaux composition (tribasic copper sulfate), elemental sulfur, ferbam, mancozeb, maneb, metiram, propineb, thiram, zinc thiazole, zineb, ziram, folpet, captan, captafol, chlorothalonil, dichlofluanid, trifluanid, guazatine, iminoctadine albesilate, iminoctadine triacetate, anilazine, dithianon, quinomethionate, and fluoroimides.

[0235] Embodiment C56. The composition of embodiment C1, wherein component (b) comprises at least one compound selected from (b53) biological fungicides with multiple mechanisms of action, such as extracts from cotyledons of lupine plantlets.

[0236] Embodiment C57. Component (b) is any of (b54) bethoxadin, cyflufenamid, dichlorobenthiazox, dipimethitron, dodine, ferimzone, flometoquin, fluthianil, neoazodine, picarbutrazox, pyrrolnitrin, tebufloquine, tolnifanide, N'-[4-[4-chloro-3-(trifluoromethyl)phenoxy]-2,5-dimethylphenyl]-N-ethyl-N-methylmethanimidami The composition of embodiment C1, comprising at least one compound selected from a fungicide other than the fungicides of components (a1) and (a2) and components (b1) through (b53), such as 4-fluorophenyl N-[1-[[[1-(4-cyanophenyl)ethyl]sulfonyl]methyl]propyl]carbamate (XR-539).

[0237] Embodiment C58. The composition of Embodiment C1 wherein component (b) comprises 3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenylpyridazine (tentatively named pyridaclomethyl).

[0238] Embodiment C59. The composition of Embodiment C1 wherein component (b) comprises aminopyrifen.

[0239] Embodiment C60. The embodiment C60 wherein component (b) is selected from the group consisting of azoxystrobin, benzovindiflupyr, boscalid (nicobifen), bixafen, bromuconazole, carbendazim, chlorothalonil, copper sulfate, cyflufenamid, cyproconazole, difenoconazole, dimoxystrobin, epoxiconazole, famoxadone, fenbuconazole, fenpropidin, fenpropimorph, florylpicoxamide, fluindapyr, flusilazole, flutriafol, and fluoxapi. Loxad, hexaconazole, impilfluxam, ipconazole, isoflucipram, kresoxim-methyl, mancozeb, mefentrifluconazole, manzate, metconazole, metominostrobin, metrafenone, methyltetraprole, myclobutanil, penconazole, penthiopyrad, picoxystrobin, prochloraz, propiconazole, proquinazid, prothioconazole, pydiflumetofen, pyraclostrobin, pyrametostrobin, pirametostrobin Roxistrobin, pyriophenone, quinoxyfen, tebuconazole, trifloxystrobin, triticonazole, N-(2,2,2-trifluoroethyl)-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-4-oxazolecarboxamide, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenoxy]methyl]-1H-pyrazole-4-carboxylate ethyl 1-[[4-[[(1Z)-2-ethoxy-3,3,3-trifluoro-1-propen-1-yl]oxy]phenyl]methyl]-1H-pyrazole-4-carboxylate, ethyl 1-[[4-[[(1Z)-2-ethoxy-3,3,3-trifluoro-1-propen-1-yl]oxy]phenyl]methyl]-1H-pyrazole-4-carboxylate, and ethyl 1-[[4-[[2-(trifluoromethyl)-1,3-dioxolan-2-yl]methoxy]phenyl]methyl]-1H-pyrazole-4-carboxylate.

[0240] Embodiment C61. The embodiment C61 in which component (b) is selected from the group consisting of azoxystrobin, benzovindiflupyr, bixafen, chlorothalonil, copper sulfate, cyflufenamid, cyproconazole, difenoconazole, dimoxystrobin, epoxiconazole, famoxadone, fenpropidin, fenpropimorph, florylpicoxamide, fluindapyr, flusilazole, flutriafol, fluxapyroxad, inpirfluxam, isoflurane, kresoxim-methyl, mancozeb, manzate, mefentrifluconazole, metconazole, metominostrobin, metrafenone, myclobutanil, penthiopyrad, picoxystrobin, propiconazole, proquinazide, prothioconazole, pydiflumetofen, pyraclostrobin, pyrametostrobin, pyroxystrobin, pyriophenone, quinoxyfen, tebuconazole, trifluro The composition of embodiment C60, comprising at least one compound selected from the group consisting of oxystrobin, triticonazole, N-(2,2,2-trifluoroethyl)-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-4-oxazolecarboxamide, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenoxy]methyl]-1H-pyrazole-4-carboxylate, ethyl 1-[[4-[[(1Z)-2-ethoxy-3,3,3-trifluoro-1-propen-1-yl]oxy]phenyl]methyl]-1H-pyrazole-4-carboxylate, and ethyl 1-[[4-[[2-(trifluoromethyl)-1,3-dioxolan-2-yl]methoxy]phenyl]methyl]-1H-pyrazole-4-carboxylate.

[0241] Embodiment C62. The embodiment C62 in which component (b) is selected from the group consisting of azoxystrobin, benzovindiflupyr, bixafen, chlorothalonil, copper sulfate, cyproconazole, difenoconazole, epoxiconazole, fenpropimorph, florylpicoxamide, fluindapyr, flutriafol, fluxapyroxad, inpirfluxam, isoflucipram, mancozeb, mefentrifluconazole, metominostrobin, picoxystrobin, prothioconazole, pydiflumetofen, pyraclostrobin, The composition of embodiment C61, comprising at least one compound selected from the group consisting of tebuconazole, trifloxystrobin, ethyl 1-[[4-[[(1Z)-2-ethoxy-3,3,3-trifluoro-1-propen-1-yl]oxy]phenyl]methyl]-1H-pyrazole-4-carboxylate, and ethyl 1-[[4-[[2-(trifluoromethyl)-1,3-dioxolan-2-yl]methoxy]phenyl]methyl]-1H-pyrazole-4-carboxylate.

[0242] Embodiment C63. The composition of embodiment C62 wherein component (b) comprises at least one compound selected from the group consisting of azoxystrobin, benzovindiflupyr, bixafen, chlorothalonil, copper sulfate, cyproconazole, difenoconazole, epoxiconazole, fenpropimorph, florylpicoxamide, fluindapyr, flutriafol, fluxapyroxad, inpirfluxam, isoflucipram, mancozeb, mefentrifluconazole, metominostrobin, picoxystrobin, prothioconazole, pydiflumetofen, pyraclostrobin, tebuconazole, and trifloxystrobin.

[0243] Embodiment C64. The composition of embodiment C63 wherein component (b) comprises at least one compound selected from the group consisting of azoxystrobin, benzovindiflupyr, chlorothalonil, cyproconazole, difenoconazole, epoxiconazole, fenpropimorph, fluindapyr, flutriafol, mancozeb, mefentrifluconazole, picoxystrobin, prothioconazole, pydiflumetofen, tebuconazole, and trifloxystrobin.

[0244] Embodiment C65. The composition of embodiment C1 wherein component (b) comprises at least one compound selected from the group consisting of azoxystrobin, benzovindiflupyr, chlorothalonil, cyproconazole, difenoconazole, epoxiconazole, fenpropimorph, fluindapyr, flutriafol, mancozeb, mefentrifluconazole, methallylpicoxamide, picoxystrobin, prothioconazole, pydiflumetofen, tebuconazole, and trifloxystrobin.

[0245] Embodiment C66. Component (b) is The composition of embodiment C1, comprising at least two fungicidal compounds selected from the group consisting of azoxystrobin, benzovindiflupyr, bixafen, chlorothalonil, copper sulfate, cyproconazole, difenoconazole, epoxiconazole, fenpropimorph, florylpicoxamide, fluindapyr, flutriafol, fluxapyroxad, inpirfluxam, isoflucipram, mancozeb, mefentrifluconazole, metominostrobin, picoxystrobin, prothioconazole, pydiflumetofen, pyraclostrobin, tebuconazole, and trifloxystrobin.

[0246] Of note, in any one of the compositions of the embodiments described herein, reference to Formula I or Formula II includes salts thereof but not N-oxides thereof, and thus the phrase "a compound of Formula I" or "a compound of Formula II" can be replaced with the phrase "a compound of Formula I or a salt thereof" or "a compound of Formula II or a salt thereof."

[0247] Also of note as an embodiment is a fungicidal composition of the present invention comprising a fungicidally effective amount of any one of the compositions of the embodiments described herein and at least one additional component selected from the group consisting of surfactants, solid diluents, and liquid diluents.

[0248] Embodiments of the present invention further include a method for controlling plant diseases caused by fungal plant pathogens, comprising applying to a plant or part thereof, or to a seed or seedling of a plant, a fungicidally effective amount of the composition of any one of the embodiments described herein. Embodiments of the present invention also include a method for protecting a plant or plant seed from disease caused by a fungal pathogen, comprising applying to the plant or plant seed a fungicidally effective amount of the composition of any one of the embodiments described herein.

[0249] Some embodiments of the present invention involve the control or protection of plant diseases that primarily affect the plant's foliage, and / or involve applying the compositions of the present invention to the plant's foliage (i.e., to the plant instead of the seeds). Preferred methods of use include those that include the preferred compositions described above; diseases that are particularly effectively controlled include plant diseases caused by fungal plant pathogens. The fungicide combinations used in accordance with the present invention can promote disease control and delay resistance development. Furthermore, the fungicide combinations used in accordance with the present invention can be particularly effective against fungal species that are resistant to fungicides.

[0250] Embodiment D1. The composition described in the Summary of the Invention wherein the SDHI and picolinamide are present in a ratio of SDHI:picolinamide ranging from about 20:1 to about 1:20.

[0251] Embodiment D2. The composition of embodiment D1 wherein the SDHI and picolinamide are present in a ratio of SDHI:picolinamide ranging from about 10:1 to about 1:10.

[0252] Embodiment D3. The composition of embodiment D2 wherein the SDHI and picolinamide are present in a ratio of SDHI:picolinamide ranging from about 9:1 to about 1:9.

[0253] Embodiment D4. The composition of embodiment D3 wherein the SDHI and picolinamide are present in a ratio of SDHI:picolinamide ranging from about 8:1 to about 1:8.

[0254] Embodiment D5. The composition of embodiment D4 wherein the SDHI and picolinamide are present in a ratio of SDHI:picolinamide ranging from about 7:1 to about 1:7.

[0255] Embodiment D6 The composition of embodiment D5 wherein the SDHI and picolinamide are present in a ratio of SDHI:picolinamide ranging from about 6:1 to about 1:6.

[0256] Embodiment D7. The composition of embodiment D6 wherein the SDHI and picolinamide are present in a ratio of SDHI:picolinamide ranging from about 5:1 to about 1:5.

[0257] Embodiment D8. The composition of embodiment D7 wherein the SDHI and picolinamide are present in a ratio of SDHI:picolinamide ranging from about 4:1 to about 1:4.

[0258] Embodiment D9. The composition of embodiment D8 wherein the SDHI and picolinamide are present in a ratio of SDHI:picolinamide ranging from about 3:1 to about 1:3.

[0259] Embodiment D10. The composition of embodiment D9 wherein the SDHI and picolinamide are present in a ratio of SDHI:picolinamide ranging from about 2:1 to about 1:2.

[0260] Embodiment D11 The composition of embodiment D10 wherein the SDHI and picolinamide are present in a ratio of SDHI:picolinamide of about 1.5:1. The method embodiment further includes:

[0261] Embodiment E1. A method for protecting a plant from a disease selected from rust disease, powdery mildew disease, Septoria disease, and Botrytis diseases comprising applying to the plant a fungicidally effective amount of a composition described in the Summary of the Invention or any one of the embodiments described herein.

[0262] Embodiment E2. The method of embodiment E1 wherein the disease is rust and component (b) of the composition comprises at least one fungicidal compound selected from (b3) demethylation inhibitor (DMI) fungicides, (b5) amine / morpholine fungicides, (b7) succinate dehydrogenase inhibitor fungicides, (b11) quinone outside inhibitor (QoI) fungicides, (b13) methyl benzimidazole carbamate fungicides, and (b52) multi-site active fungicides.

[0263] Embodiment E3. The method of embodiment E2, wherein component (b) of the composition comprises at least one fungicidal compound selected from (b3) a demethylation inhibitor (DMI) fungicide, (b7) a succinate dehydrogenase inhibitor fungicide, (b11) a quinone outside inhibitor (QoI) fungicide, and (b52) a multi-site active fungicide.

[0264] Embodiment E4. The method of embodiment E3, wherein component (b) of the composition comprises at least one fungicidal compound selected from (b3) a demethylation inhibitor (DMI) fungicide, (b7) a succinate dehydrogenase inhibitor fungicide, and (b11) a quinone outside inhibitor (QoI).

[0265] Embodiment E5. The method of embodiment E1, wherein component (b) of the composition comprises at least one fungicidal compound selected from the group consisting of azoxystrobin, benzovindiflupyr, bixafen, cyproconazole, difenoconazole, epoxiconazole, fenpropimorph, florylpicoxamide, fluindapyr, flutriafol, fluxapyroxad, inpirfluxam, isoflucipram, mancozeb, mefentrifluconazole, metominostrobin, picoxystrobin, prothioconazole, pydiflumetofen, pyraclostrobin, tebuconazole, and trifloxystrobin.

[0266] Embodiment E6. The method of embodiment E5, wherein component (b) of the composition comprises at least one fungicidal compound selected from the group consisting of azoxystrobin, benzovindiflupyr, cyproconazole, epoxiconazole, fenpropimorph, flutriafol, fluxapyroxad, metominostrobin, picoxystrobin, prothioconazole, pydiflumetofen, tebuconazole, and trifloxystrobin.

[0267] Embodiment E7 The method of embodiment E2, wherein the disease is Asian soybean rust caused by Phakopsora pachyrhizi.

[0268] Embodiment E8 The method of embodiment E2, wherein the disease is wheat leaf rust caused by Puccinia recondita.

[0269] Embodiment E9. The method of embodiment E1, wherein the disease is powdery mildew and component (b) of the composition comprises at least one fungicidal compound selected from (b3) a demethylation inhibitor (DMI) fungicide, (b11) a quinine outside inhibitor (QoI) fungicide, (b13) an azanaphthalene fungicide, and (b52) a multi-site active fungicide.

[0270] Embodiment E10. The method of embodiment E9, wherein component (b) of the composition comprises at least one fungicidal compound selected from (b3) a demethylation inhibitor (DMI) fungicide, (b11) a quinone outside inhibitor (QoI) fungicide, and (b52) a multi-site active fungicide.

[0271] Embodiment E11. The method of embodiment E9, wherein component (b) of the composition comprises at least one fungicidal compound selected from the group consisting of azoxystrobin, chlorothalonil, copper sulfate, cyproconazole, difenoconazole, epoxiconazole, flutriafol, mancozeb, mefentrifluconazole, metominostrobin, picoxystrobin, prothioconazole, pyraclostrobin, tebuconazole, and trifloxystrobin.

[0272] Embodiment E12. The method of embodiment E11 wherein component (b) of the composition comprises at least one fungicidal compound selected from the group consisting of cyproconazole, difenoconazole, epoxiconazole, flutriafol, mancozeb, prothioconazole, tebuconazole, and trifloxystrobin.

[0273] Embodiment E13 The method of Embodiment E10 wherein component (b) of the composition comprises at least one fungicidal compound selected from (b3) a DMI fungicide.

[0274] Embodiment E14. The method of embodiment E13 wherein component (b) of the composition comprises at least one fungicidal compound selected from the group consisting of cyproconazole, difenoconazole, epoxiconazole, flutriafol, prothioconazole and tebuconazole.

[0275] Embodiment E15. The method of embodiment E10 wherein component (b) of the composition comprises at least one fungicidal compound selected from (b11) Qol fungicides.

[0276] Embodiment E16. The method of embodiment E15 wherein component (b) of the composition comprises at least one fungicidal compound selected from the group consisting of azoxystrobin, picoxystrobin, pyraclostrobin, and trifloxystrobin.

[0277] Embodiment E17 The method of embodiment E9, wherein the disease is wheat powdery mildew caused by Erysiphe graminis.

[0278] Embodiment E18. The method of embodiment E1, wherein the disease is septoria and component (b) of the composition comprises at least one fungicidal compound selected from (b3) a demethylation inhibitor (DMI) fungicide, and (b11) a quinine outside inhibitor (QoI) fungicide.

[0279] Embodiment E19. The method of Embodiment E18 wherein component (b) of the composition comprises at least one fungicidal compound selected from the group consisting of azoxystrobin, cyproconazole, difenoconazole, epoxiconazole, fenpropimorph, florylpicoxamide, flutriafol, mefentrifluconazole, metominostrobin, picoxystrobin, prothioconazole, pyraclostrobin, tebuconazole, and trifloxystrobin.

[0280] Embodiment E20. The method of embodiment E18, wherein the disease is wheat leaf blotch caused by Zymoseptoria tritici.

[0281] Embodiment E21. The method of embodiment E1, wherein the disease is Botrytis cinerea and component (b) of the composition comprises at least one fungicidal compound selected from (b11) a quinone outside inhibitor (QoI) fungicide, and (b52) a multi-site active fungicide.

[0282] Embodiment E22. The method of embodiment E21 wherein component (b) of the composition comprises at least one fungicidal compound selected from the group consisting of azoxystrobin, chlorothalonil, mancozeb, metominostrobin, picoxystrobin, pyraclostrobin, and trifloxystrobin.

[0283] Embodiment E23 The method of embodiment E22 wherein component (b) of the composition comprises at least one fungicidal compound selected from the group consisting of azoxystrobin, mancozeb, and trifloxystrobin.

[0284] Embodiment E24 The method of Embodiment E1 wherein components (a1), (a2), and (b) are applied in synergistically effective amounts (and in synergistic ratios relative to one another).

[0285] The method embodiments also include:

[0286] Embodiment F1. A method for protecting a plant from disease caused by a resistant strain of at least one fungus comprising applying to the plant a fungicidally effective amount of a composition described in the Summary of the Invention or any one of the embodiments described herein.

[0287] Embodiment F2 The method of embodiment F1, wherein the resistant strain of fungus develops as a result of cross-resistance.

[0288] Embodiment F3 The method of embodiment F1, wherein the resistant strain of fungus arises as a result of a genetic mutation.

[0289] Embodiment F4 The method of any one of embodiments F1-F3, wherein the resistant strain of fungus is resistant to at least one SDHI fungicide (succinate dehydrogenase inhibitor).

[0290] Embodiment F5. The method of embodiment F4, wherein the resistant strain of fungus is resistant to at least one SDHI fungicide when the wild type of the strain is sensitive to the fungicide.

[0291] Embodiment F6. The method according to claim 1, wherein the resistant strain of fungus is selected from the group consisting of Alternaria alternata, Alternaria solani, Aspergillus oryzae, Botrytis cinerea, Corynespora cassiicola, Didymella bryoniae, Erysiphe necator, Phakopsora pachyrhizi, Podosphaera xanthii, Puccinia hordei, Puccinia triticina, Pyrenophora teres, and the like. teres, Ramularia collo-cygni, Rhynchosporium secalis, Sclerotinia sclerotiorum, Stemphylium botryose, Ustilago maydis, Venturia inaequalis, and Zymoseptoria tritici.

[0292] Embodiment F7. The method according to claim 1, wherein the resistant strain of fungus is selected from the group consisting of Alternaria alternata, Alternaria solani, Aspergillus oryzae, Botrytis cinerea, Botrytis elliptica, Corynespora cassiicola, Didymella bryoniae, Mycosphaerella graminicola, Podosphaera xanthii, Sclerotinia sclerotiorum, Stemphylium botryosum, Ustilago maydis, and the like. The method of any one of embodiments F1 to F5, wherein the fungus is selected from: Maydis, and Zymoseptoria tritici.

[0293] Embodiment F8 The method of embodiments F6 and F7, wherein the resistant strain of fungus is Zymoseptoria tritici.

[0294] Embodiment F9 The method of embodiment F8, wherein the Zymoseptoria tritici is strain IPO323.

[0295] Embodiment F10 The method of embodiment F8, wherein the Zymoseptoria tritici comprises at least one mutation in the CYP51 gene.

[0296] Embodiment F11 The method of embodiment F8, wherein the Zymoseptoria tritici comprises at least two mutations in the CYP51 gene.

[0297] Embodiment F12 The method of embodiment F8, wherein the Zymoseptoria tritici is strain TriR6.

[0298] Embodiment F12. The method of embodiment F8, wherein the Zymoseptoria tritici is strain TriR10.

[0299] Of note are counterparts to Embodiments E1 to E24 and Embodiments F1 to F12 which relate to methods of controlling plant diseases caused by fungal plant pathogens comprising applying to a plant or part thereof a fungicidally effective amount of a fungicidal composition of the present invention.

[0300] Formulation / Practical Use The (a1) SDHIs and (a2) picolinamides described in the Summary of the Invention will generally be used as the fungicidal active ingredient in a composition, i.e., a formulation, along with at least one additional ingredient selected from the group consisting of surfactants, solid diluents, and liquid diluents, which acts as a carrier. The formulation or composition ingredients are selected to be consistent with the physical properties of the active ingredient, the application mode, and environmental factors such as soil type, moisture, and temperature.

[0301] Mixtures of components (a1) and (a2) with component (b) (e.g., selected from (b1)-(b54) above and salts thereof) and / or one or more other biologically active compounds or agents (i.e., insecticides, other fungicides, nematicides, miticides, herbicides and other biological agents) can be formulated in a number of ways, including the following: (i) component (a1), component (a2), component (b) and / or one or more other biologically active compounds or agents may be formulated separately and applied separately or may be applied simultaneously in appropriate weight ratios, e.g., as a tank mix; or (ii) Component (a1), component (a2), component (b) and / or one or more other biologically active compounds or agents may be blended together in a suitable weight ratio.

[0302] Useful formulations include both liquid and solid compositions. Liquid compositions include solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions, oil-in-water emulsions, flowable concentrates, and / or suspoemulsions), which can optionally be concentrated into gels. Common types of aqueous liquid compositions include soluble concentrates, suspension concentrates, capsule suspensions, concentrated emulsions, microemulsions, oil-in-water emulsions, flowable concentrates, and suspoemulsions. Common types of non-aqueous liquid compositions are emulsifiable concentrates, microemulsifiable concentrates, dispersible concentrates, and oil dispersions.

[0303] Common types of solid compositions include dusts, powders, granules, pellets, prills, pastilles, tablets, and filled films (including seed coatings), which can be water-dispersible ("wettable") or water-soluble. Films and coatings formed from film-forming solutions or flowable suspensions are particularly useful for seed treatments. Active ingredients can be (micro)encapsulated and further processed into suspensions or solid formulations; alternatively, entire formulations of active ingredients can be encapsulated (or "overcoated"). Encapsulation can control or delay the release of the active ingredient. Emulsifiable granules combine the advantages of both emulsifiable concentrate and dry granule formulations. High-strength compositions are primarily used as intermediates for further formulation.

[0304] In one composition embodiment, granules of a solid composition comprising components (a1) and (a2) are mixed with granules of a solid composition comprising component (b). These mixtures can be further mixed with granules comprising an additional agricultural protectant. Alternatively, two or more agricultural protectants (e.g., components (a1), (a2), and (b) compounds, agricultural protectants other than components (a1) or (a2) or (b)) can be combined in a set of granules of a solid composition, which can then be mixed with one or more sets of granules of a solid composition comprising one or more additional agricultural protectants. These granule mixtures can conform to the general granule mixture disclosures of PCT Patent Publication WO 94 / 24861 or, more preferably, the homogeneous granule mixture teachings of U.S. Pat. No. 6,022,552.

[0305] Sprayable formulations are typically spread in a suitable medium before spraying. Such liquid and solid formulations are formulated to be easily diluted in the spray medium, usually water, but sometimes in another suitable medium, such as an aromatic or paraffinic hydrocarbon or vegetable oil. Spray volumes can range from about one to several thousand liters per hectare, but more typically range from about 10 to several hundred liters per hectare. Sprayable formulations can be tank-mixed with water or another suitable medium for foliar treatment by aerial or ground application, or for application to the plant's growing medium. Liquid and dry formulations can be injected directly into drip irrigation systems or metered into furrows at planting. Liquid and solid formulations can be applied to seeds of crops and other desirable vegetation as seed treatments before planting to protect developing roots and other underground plant parts and / or leaves by systemic absorption.

[0306] The formulations will typically contain active ingredients, diluents, and surfactants within the following approximate ranges, which add up to 100 weight percent: As defined herein, an effective amount of active ingredient includes the individual amount of each active ingredient or a combination of two or more active ingredients.

[0307] [Table 1]

[0308] Examples of solid diluents include clays such as bentonite, montmorillonite, attapulgite, kaolin, gypsum, cellulose, titanium dioxide, zinc oxide, starch, dextrin, sugars (e.g., lactose, sucrose), silica, talc, mica, diatomaceous earth, urea, calcium carbonate, sodium carbonate and sodium bicarbonate, and sodium sulfate. Typical solid diluents are described in Watkins et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey.

[0309] Examples of liquid diluents include water, N,N-dimethylalkanamides (e.g., N,N-dimethylformamide), limonene, dimethyl sulfoxide, N-alkylpyrrolidones (e.g., N-methylpyrrolidinone), alkyl phosphates (e.g., triethyl phosphate), ethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, propylene carbonate, butylene carbonate, paraffins (e.g., white mineral oil, normal paraffin, isoparaffin), alkylbenzenes, alkylnaphthalenes, glycerin, glycerol triacetate, sorbitol, aromatic hydrocarbons, dearomatized aliphatic hydrocarbons, alkylbenzenes, alkylnaphthalenes, ketones such as cyclohexanone, 2-heptanone, isophorone, and 4-hydroxy-4-methyl-2-pentanone. , acetates, such as isoamyl acetate, hexyl acetate, heptyl acetate, octyl acetate, nonyl acetate, tridecyl acetate, and isobornyl acetate, other esters such as alkylated lactates, dibasic esters, alkyl and aryl benzoates, and γ-butyrolactone, as well as alcohols, which may be linear, branched, saturated, or unsaturated, such as methanol, ethanol, n-propanol, isopropyl alcohol, n-butanol, isobutyl alcohol, n-hexanol, 2-ethylhexanol, n-octanol, decanol, isodecyl alcohol, isooctadecanol, cetyl alcohol, lauryl alcohol, tridecyl alcohol, oleyl alcohol, cyclohexanol, tetrahydrofurfuryl alcohol, diacetone alcohol, cresol, and benzyl alcohol. Liquid diluents include saturated and unsaturated fatty acids (typically C6-C8). 22), for example, vegetable seed and fruit oils (e.g., olive, castor, linseed, sesame, corn (maize), peanut, sunflower, grapeseed, safflower, cottonseed, soybean, rapeseed, coconut, and palm kernel oils), animal-derived fats (e.g., beef tallow, pork fat, lard, cod liver oil, fish oil), and mixtures thereof. Liquid diluents also include alkylated fatty acids (e.g., methylated, ethylated, butylated), where the fatty acids can be obtained by hydrolysis of glycerol esters from vegetable and animal sources and can be purified by distillation. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950.

[0310] The solid and liquid compositions of the present invention often contain one or more surfactants. Surfactants (also known as "surface active agents"), when added to a liquid, generally modify, and in most cases reduce, the surface tension of the liquid. Depending on the nature of the hydrophilic and lipophilic groups in the surfactant molecule, surfactants can be useful as wetting agents, dispersants, emulsifiers, or antifoaming agents.

[0311] Surfactants can be classified as nonionic, anionic or cationic.Nonionic surfactants useful for the present compositions include, but are not limited to, alcohol alkoxylates, such as those based on natural and synthetic alcohols (which may be branched or linear) and prepared from alcohols and ethylene oxide, propylene oxide, butylene oxide, or mixtures thereof; amine ethoxylates, alkanolamides, and ethoxylated alkanolamides; alkoxylated triglycerides, such as ethoxylated soybean oil, castor oil, and rapeseed oil; alkyl alkoxylates, such as alkyl alkoxylates ... phenol alkoxylates, such as octylphenol ethoxylate, nonylphenol ethoxylate, dinonylphenol ethoxylate, and dodecylphenol ethoxylate (prepared from phenol and ethylene oxide, propylene oxide, butylene oxide, or mixtures thereof); block polymers prepared from ethylene oxide or propylene oxide and reverse block polymers whose end blocks are prepared from propylene oxide; ethoxylated fatty acids; ethoxylated fatty esters and oils; ethoxylated methyl ethoxylated tristyrylphenols (including those prepared from ethylene oxide, propylene oxide, butylene oxide, or mixtures thereof); fatty acid esters, glycerol esters, lanolin-based derivatives, polyethoxylate esters such as polyethoxylated sorbitan fatty acid esters, polyethoxylated sorbitol fatty acid esters, and polyethoxylated glycerol fatty acid esters; other sorbitan derivatives such as sorbitan esters; polymeric surfactants such as random copolymers, block copolymers, alkyd PEG (polyethylene glycol) resins, graft or comb polymers, and star polymers; polyethylene glycol (PEG); polyethylene glycol fatty acid esters; silicone-based surfactants; and sugar derivatives such as sucrose esters, alkyl polyglycosides, alkyl polysaccharides, and glucamides such as a mixture of octyl-N-methylglucamide and decyl-N-methylglucamide (for example, products available from Clariant under the name Synergen® GA).

[0312] Useful anionic surfactants include, but are not limited to, alkylaryl sulfonic acids and their salts; carboxylated alcohol or alkylphenol ethoxylates; diphenyl sulfonic acid derivatives; lignin and lignin derivatives such as lignosulfonates; maleic acid or succinic acid or anhydrides; olefin sulfonates, phosphate esters such as phosphate esters of alcohol alkoxylates, phosphate esters of alkylphenol alkoxylates, and phosphate esters of styrylphenol ethoxylates; protein-based surfactants; sarcosine derivatives; styrylphenol ether sulfonates; sulfates of alcohols; sulfates of ethoxylated alcohols; sulfonates of amines and amides such as N,N-alkyl taurates; sulfonates of benzene, cumene, toluene, xylene, and dodecyl and tridecyl benzene; sulfonates of condensed naphthalenes; sulfonates of naphthalene and alkyl naphthalenes; sulfonates of fractionated petroleum oils; sulfosuccinamates; and sulfosuccinates and their derivatives, such as dialkyl sulfosuccinate salts.

[0313] Useful cationic surfactants include, but are not limited to, amides and ethoxylated amides; amines such as N-alkylpropanediamines, tripropylenetriamine, and dipropylenetetramine; and ethoxylated amines, ethoxylated diamines, and propoxylated amines (prepared from amines and ethylene oxide, propylene oxide, butylene oxide, or mixtures thereof); amine salts such as amine acetates and diamine salts; quaternary ammonium salts such as quaternary salts, ethoxylated quaternary salts, and diquaternary salts; and amine oxides such as alkyldimethylamine oxides and bis-(2-hydroxyethyl)-alkylamine oxides.

[0314] Also useful in the compositions of the present invention are mixtures of nonionic and anionic surfactants or mixtures of nonionic and cationic surfactants. Nonionic, anionic, and cationic surfactants and their recommended uses are disclosed in various published references, including McCutcheon's Emulsifiers and Detergents, annual American and International Editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964; and A.S. Davidson and B. Milwidsky, Synthetic Detergents, Seventh Edition, John Wiley and Sons, New York, 1987.

[0315] The compositions of the present invention may further contain formulation aids and additives known to those skilled in the art as formulation aids, some of which may also be considered to function as solid diluents, liquid diluents, or surfactants. Such formulation aids and additives may control pH (buffering agents), foaming during processing (antifoaming agents such as polyorganosiloxanes), active ingredient settling (suspending agents), viscosity (thixotropic thickeners), microbial growth in the container (antimicrobial agents), product freezing (antifreeze agents), color (dye / pigment dispersions), wash-off (film formers or spreading agents), evaporation (evaporation retardants), and other formulation properties. Film formers include, for example, polyvinyl acetate, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinyl acetate copolymers, polyvinyl alcohol, polyvinyl alcohol copolymers, and waxes. Examples of formulation aids and additives include those described in McCutcheon's Volume 2: Functional Materials, annual International and North American editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; and PCT Publication WO 03 / 024222.

[0316] Components (a1) and (a2) and any other active ingredients are typically incorporated into the present compositions by dissolving the active ingredients in a solvent or milling them in a liquid or dry diluent. Solutions, including emulsifiable concentrates, can be prepared by simply mixing the ingredients. If the solvent of a liquid composition intended for use as an emulsifiable concentrate is not miscible with water, an emulsifier is typically added to emulsify the active-containing solvent upon dilution with water. Active ingredient slurries with particle sizes up to 2,000 μm can be wet-milled using a media mill to obtain particles with an average particle size of less than 3 μm. Aqueous slurries can be made into finished suspension concentrates (see, e.g., U.S. Pat. No. 3,060,084) or can be further processed by spray drying to form water-dispersible granules. Dry blends typically require a dry milling process that results in an average particle size in the range of 2 to 10 μm. Dusts and powders can be prepared by blending and typically milling (e.g., hammer mills or fluid energy mills). Granules and pellets can be prepared by spraying the active material onto a preformed granular carrier or by agglomeration techniques. See Browning, "Agglomeration," Chemical Engineering, December 4, 1967, pp. 147-48; Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pp. 8-57 et seq.; and WO 91 / 13546. Pellets can be prepared as described in U.S. Pat. No. 4,172,714. Water-dispersible and water-soluble granules can be prepared as taught in U.S. Pat. No. 4,144,050, U.S. Pat. No. 3,920,442, and German Patent No. 3,246,493. Tablets can be prepared as taught in U.S. Patent Nos. 5,180,587, 5,232,701, and 5,208,030. Films can be prepared as taught in British Patent No. 2,095,558 and U.S. Patent No. 3,299,566.

[0317] One embodiment of the present invention relates to a method for controlling fungal pathogens, comprising diluting the fungicidal composition of the present invention (components (a1) and (a2) combined with a surfactant, a solid diluent and a liquid diluent or a combined mixture of components (a1) and (a2) with at least one other fungicide) with water, optionally adding an adjuvant to form a diluted composition, and contacting the fungal pathogen or its environment with an effective amount of the diluted composition.

[0318] Although spray compositions formed by diluting a sufficient concentration of the fungicidal composition of the present invention with water are fully effective in controlling fungal pathogens, separately formulated adjuvant products can also be added to the spray tank mix. These additional adjuvants, commonly known as "spray adjuvants" or "tank-mix adjuvants," include any substance mixed in the spray tank to improve the performance of the pesticide or to alter the physical properties of the spray mixture. Adjuvants can be anionic or nonionic surfactants, emulsifiers, petroleum-based crop oils, crop-derived seed oils, acidifiers, buffers, thickeners, or antifoaming agents. Adjuvants are used to improve efficacy (e.g., bioavailability, adhesion, penetration, uniformity of coverage, and durability of protection) or to minimize or eliminate spray application problems related to incompatibility, foaming, drift, evaporation, volatilization, and decomposition. To achieve optimal performance, adjuvants are selected with respect to the characteristics of the active ingredient, formulation, and target (e.g., crop, insect pest).

[0319] The amount of adjuvant added to the spray mixture generally ranges from about 0.1% to 2.5% by volume. The application rate of adjuvants added to the spray mixture is generally about 1 to 5 L per hectare. Representative examples of spray adjuvants include Adigor® (Syngenta) 47% methylated rapeseed oil liquid hydrocarbon, Silwet® (Helena Chemical Company) polyalkylene oxide-modified heptamethyltrisiloxane, and Assist® (BASF) 17% surfactant blend in 83% paraffin-based mineral oil.

[0320] One method of seed treatment involves spraying or dusting the seeds with the compound of the present invention (i.e., as a formulated composition) before sowing. Compositions formulated for seed treatment generally contain a film former or adhesive. Thus, the seed coating composition of the present invention typically contains biologically effective amounts of components (a1) and (a2) and a film former or adhesive. Seeds can be coated by spraying a flowable suspension concentrate directly onto a tumbling bed of seeds and then drying the seeds. Alternatively, other formulation types, such as wettable powders, solutions, suspoemulsions, emulsifiable concentrates, and emulsions in water, can be sprayed onto the seeds. This process is particularly useful for applying film coatings to seeds. Various coating machines and processes are available to those skilled in the art. Suitable processes include those listed in P. Kosters et al., Seed Treatment: Progress and Prospects, 1994 BCPC Monograph No. 57 and the references cited therein.

[0321] For further information on formulation techniques, see T. S. Woods, "The Formulator's Toolbox - Product Forms for Modern Agriculture," in Pesticide Chemistry and Bioscience, The Food-Environment Challenge, T. Brooks and T. R. Roberts, Eds., Proceedings of the 9th International Congress on Pesticide Chemistry, The Royal Society of Chemistry, Cambridge, 1999, pp. 120-133. See also the following references: U.S. Pat. No. 3,235,361, column 6, line 16 to column 7, line 19, and Examples 10-41; U.S. Pat. No. 3,309,192, column 5, line 43 to column 7, line 62, and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167, and 169-182; U.S. Pat. No. 2,891,855, column 3, line 66 to column 5, line 17, and Examples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pp. 81-96; Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989; and Developments in formulation technology, PJB Publications, Richmond, UK, 2000.

[0322] Water-soluble and water-dispersible formulations are typically diluted with water to form aqueous compositions before application. Aqueous compositions for direct application to plants or parts thereof (e.g., spray tank compositions) typically contain at least about 1 ppm or more (e.g., 1 ppm to 100 ppm) of a compound of the invention.

[0323] Seeds are typically treated at a rate of about 0.001 g (more typically about 0.1 g) to about 10 g per kg of seed (i.e., about 0.0001 to 1% by weight of the seed before treatment). Flowable suspensions formulated for seed treatment typically contain about 0.5 to about 70% active ingredient, about 0.5 to about 30% film-forming adhesive, about 0.5 to about 20% dispersant, 0 to about 5% thickener, 0 to about 5% pigment and / or dye, 0 to about 2% antifoaming agent, 0 to about 1% preservative, and 0 to about 75% volatile liquid diluent.

[0324] The compositions of the present invention are useful as plant disease control agents. Accordingly, the present invention further includes a method for controlling plant diseases caused by fungal plant pathogens, comprising applying an effective amount of a compound of the present invention or a fungicidal composition containing said compound to a plant or part thereof to be protected, or to a plant seed to be protected. The compounds and / or compositions of the present invention provide control of diseases caused by a wide range of fungal plant pathogens in the phyla Ascomycota, Basidiomycota, Zygomycota, and fungus-like Oomycota. They are effective in controlling a wide range of plant diseases, particularly foliar pathogens of ornamental, turf, vegetable, field, cereal, and fruit crops. These pathogens include, but are not limited to, those listed in Table 1-1. For Ascomycota and Basidiomycota, the names of both the sexual / teleomorph / complete stage and the asexual / anamorph / complete stage (in parentheses) are listed where known. Synonymous names of pathogens are indicated by an equal sign, e.g., the sexual / teleomorph / complete stage name, Phaeosphaeria nodorum, followed by the corresponding asexual / anamorph / incomplete stage name, Stagnospora nodorum, and the synonymous older name, Septoria nodorum.

[0325] [Table 2]

[0326] [Table 3]

[0327] In addition to fungicidal activity, the compositions or combinations also have activity against bacteria such as Erwinia amylovora, Xanthomonas campestris, Pseudomonas syringae, and other related species. By controlling harmful microorganisms, the compositions of the present invention are useful for improving (i.e., increasing) the ratio of beneficial to harmful microorganisms in contact with crop plants or their propagation materials (e.g., seeds, corms, bulbs, tubers, cuttings) or the agricultural environment of crop plants or their propagation materials.

[0328] The compositions of the present invention are useful for treating all plants, plant parts, and seeds. Plant and seed varieties and cultivars can be obtained by conventional propagation and breeding methods or by genetic engineering methods. A genetically modified plant or seed (transgenic plant or seed) is one in which a heterologous gene (transgene) has been stably integrated into the genome of the plant or seed. A transgene defined by its specific location within the plant genome is called a transformation or transgenic event.

[0329] Transgenic plant cultivars that can be treated according to the present invention include those that are tolerant to one or more biotic stresses (pests such as nematodes, insects, mites, fungi, etc.) or abiotic stresses (drought, low temperature, soil salinity, etc.) or contain other desirable traits. Plants can be genetically modified to exhibit, for example, herbicide tolerance, insect resistance, improved oil profile, or drought tolerance characteristics.

[0330] By treating transgenic plants and seeds with the compounds of the invention, superadditive or enhanced effects can be obtained, such as reduced application rates, broadened spectrum of activity, increased tolerance to biotic / abiotic stresses, or improved storage stability, which may be greater than would be expected from a simple additive effect of applying the compounds of the invention to transgenic plants and seeds.

[0331] The compounds and compositions of the present invention are useful in seed treatments to protect seeds from plant diseases. For the purposes of this disclosure and claims, treating seeds means contacting the seeds with a biologically effective amount of a compound of the present invention, typically formulated as a composition of the present invention. This seed treatment protects the seeds from soil-borne disease pathogens and generally also protects the roots and other plant parts that come into contact with the soil of seedlings emerging from the germinated seeds. This seed treatment can also provide foliar protection through translocation of the compound of the present invention or a second active ingredient within the developing plant. Seed treatments can be applied to all types of seeds, including seeds from which plants genetically transformed to express specific traits are germinated. Representative examples include those expressing proteins toxic to invertebrate pests, such as Bacillus thuringiensis toxins, or those expressing herbicide resistance, such as glyphosate acetyltransferase, which confers tolerance to glyphosate. Seed treatment with the compounds and compositions of the present invention can also increase the vigor of plants grown from the seeds.

[0332] The compounds and compositions of the present invention are particularly useful as seed treatments for crops including, but not limited to, corn, soybeans, cotton, cereals (e.g., wheat, oats, barley, rye, and rice), potatoes, vegetables, and rapeseed.

[0333] Furthermore, the compounds and compositions of the present invention are useful for treating postharvest diseases of fruits and vegetables caused by fungi, oomycetes, and bacteria. These infections can occur before, during, and after harvest. For example, infections can occur before harvest and then remain dormant until a certain point during ripening (e.g., the host begins to change tissue in a way that allows infection to progress, or conditions become favorable for disease development); infections can also occur from superficial wounds caused by machinery or insect damage. In this regard, the compositions of the present invention can reduce losses (i.e., losses due to quantity and quality) due to postharvest diseases that can occur any time between harvest and consumption. Treatment of postharvest diseases with the compounds of the present invention can increase the period during which fresh edible plant parts (e.g., fruits, seeds, leaves, stems, bulbs, tubers) can be stored refrigerated or unrefrigerated after harvest, remain edible, and are free from significant or harmful deterioration or contamination by fungi or other microorganisms. Pre- or post-harvest treatment of edible plant parts with the compounds of the invention may also reduce the production of toxic metabolites of fungi or other microorganisms, such as mycotoxins, including aflatoxins.

[0334] Control of plant diseases is typically achieved by applying an effective amount of the compounds of the present invention to the parts of the plant to be protected, such as roots, stems, leaves, fruits, seeds, tubers, or bulbs, or to the medium (soil or sand) in which the plant to be protected is growing, either before or after infection. The compounds can also be applied to seeds to protect the seeds and the seedlings that emerge from them. The compounds can also be applied to treat plants through irrigation water. Control of postharvest pathogens that infect produce before harvest is typically achieved by field application of the compounds of the present invention; when infection occurs after harvest, the compounds can be applied to the harvested crop as a dip, spray, fumigant, treatment wrap, or box liner.

[0335] The compounds and compositions of the present invention can also be applied using unmanned aerial vehicles (UAVs) to distribute the compositions disclosed herein over a planted area. In some embodiments, the cultivated area is an area containing crops. In some embodiments, the crop is selected from monocotyledonous or dicotyledonous plants. In some embodiments, the crop is selected from rice, corn, barley, buckwheat, wheat, vegetables, tobacco, tea plants, fruit trees, and sugarcane. In some embodiments, the compositions disclosed herein are formulated for spraying at very low volumes. Products applied by drones can use water or oil as the spray carrier. Typical spray volumes (including product) used worldwide for drone application are 5.0 liters / hectare to 100 liters / hectare (approximately 0.5 to 10 gpa). This ranges from ultra-low spray volume (ULV) to low spray volume (LV). Although not common, there may be situations where even lower spray volumes, such as 1.0 liter / ha (0.1 gpa), are used.

[0336] Suitable application rates (e.g., fungicidally effective amounts) of component (a1) and component (a2) and suitable application rates (e.g., biologically effective amounts, fungicidally effective amounts, or insecticidally effective amounts) of mixtures and compositions comprising component (a1) and component (a2) according to the present invention are influenced by factors such as the plant disease to be controlled (including diseases caused by known resistant strains of fungi), the plant species to be protected, the population structure of the pathogen to be controlled, ambient moisture and temperature, and should be determined under actual use conditions. Those skilled in the art can easily determine the fungicidally effective amount required for the desired level of plant disease control through simple experimentation. Protection of leaves is usually possible when treated at a rate of less than about 1 g / ha to about 5,000 g / ha of active ingredient. Protection of seeds and seedlings is usually possible when treated at a rate of about 0.001 g (more typically about 0.1 g) to about 10 g per kg of seed. Those skilled in the art can easily determine by simple experimentation the application rates of component (a1) and component (a2) containing the particular combination of active ingredients according to the present invention, and mixtures and compositions thereof, required to provide the desired range of plant protection and control of plant diseases and, optionally, other plant pests.

[0337] The compounds and compositions of the present invention may also be useful for increasing the vigor of crop plants. This method involves contacting a crop plant (e.g., leaves, flowers, fruits, or roots) or a seed from which the crop plant grows with a composition containing components (a1) and (a2) in an amount sufficient to achieve the desired plant vigor effect (i.e., a biologically effective amount). Typically, components (a1) and (a2) are applied as a formulated composition. Components (a1) and (a2) are often applied directly to the crop plant or its seeds, but they can also be applied to the location of the crop plant, i.e., to a portion of the environment of the crop plant, particularly one sufficiently close to the environment for components (a1) and (a2) to be transferred to the crop plant. The location relevant to this method most commonly includes the growth medium in which the plant is grown (i.e., the medium that provides nutrients to the plant), typically soil. Thus, treating a crop plant to increase the vigor of the crop plant comprises contacting the crop plant, the seed from which the crop plant grows, or the locus of the crop plant with a biologically effective amount of component (a1) and component (a2).

[0338] Increased crop vigor can result in one or more of the following observed effects: (a) optimal crop growth as indicated by superior seed germination, crop emergence, and crop stand; (b) improved crop growth as indicated by rapid and robust leaf growth (e.g., as measured by leaf area index), plant height, number of tillers (e.g., in the case of rice), root mass, and total dry weight of the growing parts of the crop; (c) improved crop yield as indicated by time to flowering, flowering duration, number of flowers, total biomass accumulation (i.e., yield), and / or marketability of the fruit or grain grade of the product (i.e., yield quality); (d) improved ability of crops to resist or prevent infection by plant diseases and infestation by arthropod, nematode, or mollusk pests; and (e) improved ability of crops to tolerate environmental stresses, such as extreme temperatures, suboptimal moisture, or exposure to phytotoxic chemicals.

[0339] The compounds and compositions of the present invention can increase the vigor of treated plants compared to untreated plants by preventing and / or curing plant diseases caused by fungal plant pathogens in the plant's environment. In the absence of such plant disease control, the disease reduces plant vigor by consuming plant tissue or sap or transmitting plant pathogens such as viruses. Even in the absence of fungal plant pathogens, the compounds of the present invention can increase plant vigor by altering plant metabolism. Generally, the vigor of crop plants will be most significantly increased by treating them with the compounds of the present invention when the plants are grown in a non-ideal environment, i.e., an environment that contains one or more unfavorable aspects that prevent the plants from achieving the full genetic potential they would exhibit in an ideal environment.

[0340] Of note are methods for increasing the vigor of crop plants grown in an environment that includes a plant disease caused by a fungal plant pathogen. Also of note are methods for increasing the vigor of crop plants grown in an environment that does not include a plant disease caused by a fungal plant pathogen. Also of note are methods for increasing the vigor of crop plants grown in an environment that includes an amount of moisture that is not ideal for supporting crop plant growth.

[0341] The compounds and compositions of the present invention can be mixed with one or more other biologically active compounds or agents, including fungicides, insecticides, nematicides, fungicides, acaricides, herbicides, herbicide antidotes, growth regulators, such as insect molting inhibitors and root stimulators, chemical hemostats, semi-chemicals, repellents, attractants, pheromones, feeding stimulants, plant nutrients, other biologically active compounds, or insect pathogenic bacteria, viruses, or fungi, to form multi-component insecticides that provide a broader spectrum of agricultural protection. Thus, the present invention also relates to compositions comprising (fungicidally effective amounts of) component (a1) and component (a2) and (biologically effective amounts) at least one additional biologically active compound or agent, which may further comprise at least one surfactant, solid diluent, or liquid diluent. Other biologically active compounds or agents can be incorporated into compositions comprising at least one surfactant, solid diluent, or liquid diluent. In the case of the mixtures of the present invention, one or more other biologically active compounds or agents can be blended together with one or both of components (a1) and (a2) to form a premix, or one or more other biologically active compounds or agents can be blended separately from components (a1) and (a2) and the blends can be combined together (e.g., in a spray tank) prior to application or applied sequentially.

[0342] As described in the Summary of the Invention, one aspect of the present invention is a fungicidal composition comprising components (a1) and (a2) and at least one other fungicide (i.e., component (b)). Of note are such combinations in which the other fungicidal active ingredient has a different site of action from component (a1) and / or component (a2). In certain instances, combinations with at least one other fungicidal active ingredient having a similar control spectrum but a different site of action are particularly advantageous for resistance management. Thus, the compositions of the present invention can further comprise a fungicidally effective amount of at least one additional fungicidal active ingredient having a similar control spectrum but a different site of action.

[0343] Examples of the component (b) fungicide include acibenzolar-S-methyl, aldimorph, ametocladine, amisulbrom, anilazine, azaconazole, azoxystrobin, benalaxyl (including benalaxyl-M), benodanil, benomyl, benciavalicarb (including benciavalicarb-isopropyl), benzovindiflupyr, befoxazine, binapacryl, biphenyl, bitertanol, bixafen, blasticidin-S, boscalid, bromuconazole, bupirimate, buthiobate, captafol, captan, carbendazim, and carboxin. , carpropamid, chloroneb, chlorothalonil, chlozolinate, clotrimazole, copper hydroxide, copper oxychloride, copper sulfate, cumoxystrobin, cyazofamid, cyflufenamid, cymoxanil, cyproconazole, cyprodinil, dichlofluanid, diclocymet, diclomedine, dicloran, diethofencarb, difenoconazole, diflumetrim, dimethirimol, dimethomorph, dimoxystrobin, diniconazole (including diniconazole-M), dinocap, dithianon, dithiolane, dodemorph, dodine, dipimethitron, econazole , edifenphos, enoxastrobin (also known as enestrobrin), epoxiconazole, etaconazole, ethaboxam, ethirimol, etridiazole, famoxadone, fenamidone, fenarimol, phenaminestrobin, fenbuconazole, fenfuram, fenhexamid, fenoxanil, fenpiclonil, fenpropidin, fenpropimorph, fenprirazamin, fentin acetate, fentin chloride, fentin hydroxide, ferbam, ferimzone, flometoquin, flurylpicoxamide, flucloxin Azinam, fludioxonil, flufenoxystrobin, fluindapyr, flumorph, fluopicolide, fluopimomide, fluopyram, fluorimide, floxastrobin, fluquinconazole, flusilazole, flusulfamide, flutianil, flutolanil, flutriafol, fluxapyroxad, folpet, phthalide, fuberidazole, furalaxyl, furametpyr, guazatine, hexaconazole, hymexazole, imazalil, imibenconazole, iminoctadine albesilate, iminoctadine triacetate, iodocarb,Ipconazole, ipfentrifluconazole, iprobenfos, iprodione, iprovalicarb, isoconazole, isofenamide, isoprothiolane, isoflucipram, isopyrazam, isotianil, kasugamycin, kresoxim-methyl, mancozeb, mandepropamide, mandestrobin, maneb, mepanipyrim, mepronil, meptyldinocap, metalaxyl (including metalaxylyl-M / mefenoxam), mefentrifluconazole, meconazole, methasulfocarb, metiram, metronidazole, metrafenone, metrifluconazole Conazole, myclobutanil, naftifine, neo-asozin, nuarimol, octhilinone, ofurase, orysastrobin, oxadixyl, oxathiapiprolin, oxolinic acid, oxpoconazole, oxycarboxin, oxytetracycline, pefurazoate, penconazole, pencycuron, perflufen, penthiopyrad, phosphoric acid (including its salts, e.g., fosetyl-aluminum), picarbutrazox, picoxystrobin, piperalin, polyoxin, probenazole, prochloraz, procymidone, propamacarb, propico benzodiazepine, propineb, proquinazid, prothiocarb, prothioconazole, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyrazophos, pyribencarb, pyributicarb, pyrifenox, pyrimethanil, pyriophenone, pyrisoxazole, pyroquilon, pyrrolnitrin, quinconazole, quinofumelin (Registration number 861647-84-9), quinomethionate, quinoxyfen, quintozene, sedaxane, silthiofam, simeconazole, spiroxamine, streptomycin, sulfur, tebuconazole, tebufloquine, tec Loftaram, tecnazene, terbinafine, tetraconazole, thiabendazole, thifluzamide, thiophanate, thiophanate-methyl, thiram, tiadinil, tolclofos-methyl, tolnifanide, tolprocarb, trifluanid, triadimefon, triadimenol, triarimol, triticonazole, triazoxide, tribasic copper sulfate, tricyclazole, triclopiricarb, tridemorph, trifloxystrobin, triflumizole, triforine, trimorphamide, uniconazole, uniconazole-P, validamycin,Valifenalate (also known as valifenal), vinclozolin, zineb, ziram, zoxamide, N-[2-(1S,2R)-[1,1'-bicyclopropyl]-2-ylphenyl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, α-(1-chlorocyclopropyl)-α-[2-(2,2-dichlorocyclopropyl)ethyl]-1H-1,2,4-triazole-1-ethanol, (αS)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-4-isoxazoline 1-[[(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-2-oxiranyl]methyl]-1H-1,2,4-triazole, 1-[[(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-2-oxiranyl]methyl]-1,2-dihydro-3H-1,2,4-triazole-3-thione, 1-[[(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-2-oxiranyl]methyl]- N-[2-[4-[[3-(4-chlorophenyl)-2-propyn-1-yl]oxy]-3-methoxyphenyl]ethyl]-3-methyl-2-[(methylsulfonyl)amino]butanamide, N-[2-[4-[[3-(4-chlorophenyl)-2-propyn-1-yl]oxy]-3-methoxyphenyl]ethyl]-3-methyl-2-[(ethylsulfonyl)amino]butanamide, N'-[4-[4-chloro-3-(trifluoromethyl)phenoxy]- 2,5-dimethylphenyl]-N-ethyl-N-methylmethanimidamide, N-[2-(2,4-dichlorophenyl)-2-methoxy-1-methylethyl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, N-(3',4'-difluoro[1,1'-biphenyl]-2-yl)-3-(trifluoromethyl)-2-pyrazinecarboxamide, 3-(difluoromethyl)-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-1-methyl-1H-pyrazole-4-carboxamide,5,8-difluoro-N-[2-[3-methoxy-4-[[4-(trifluoromethyl)-2-pyridinyl]oxy]phenyl]ethyl]-4-quinazolinamine, 1-[4-[4-[5R-[(2,6-difluorophenoxy)methyl]-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-1-piperdinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone, 4-fluorophenyl N-[1-[[[1-(4-cyanophenyl)ethyl]sulfonyl]methyl]propyl]carbamate, These include 5-fluoro-2-[(4-fluorophenyl)-methoxy]-4-pyrimidinamine, α-(methoxyimino)-N-methyl-2-[[[1-[3-(trifluoromethyl)phenyl]ethoxy]imino]methyl]-benzeneacetamide, and [[4-methoxy-2-[[[(3S,7R,8R,9S)-9-methyl-8-(2-methyl-1-oxopropoxy)-2,6-dioxo-7-(phenylmethyl)-1,5-dioxonan-3-yl]amino]carbonyl]-3-pyridinyl]oxy]methyl 2-methylpropanoate. Therefore, of note is a fungicidal composition comprising component (a1) and component (a2), and at least one fungicide selected from the above list as component (b).

[0344] Of particular note are ingredients (a1) and (a2), as well as aminopyrifen (registration number 1531626-08-0), azoxystrobin, benzovindiflupyr, bixafen, captan, carpropamid, chlorothalonil, copper hydroxide, copper oxychloride, copper sulfate, cymoxanil, cyproconazole, cyprodinil, diclobenthiazox (registration number 957144-77-3), diethofencarb, difenoconazole, dimethomorph, dipimethitron, epoxiconazole, ethaboxam, fenarimol, fenhexamid, flua Zinam, fludioxonil, fluindapir, fluopyram, flusilazole, flutianil, flutriafol, fluxapyroxad, folpet, ipflufenoquine (Registration number 1314008-27-9), iprodione, isofetamide, isofleflucipram, isopyrazam, kresoxim-methyl, mancozeb, mandestrobin, meptyldinocap, metalaxyl (including metalaxyl-M / mefenoxam), mefentrifluconazole, metconazole, metrafenone, methyltetraprole (Registration number 147264 9-01-6), myclobutanil, oxathiapiprolin, penflufen, penthiopyrad, phosphoric acid (including its salts, e.g., fosetyl-aluminum), picoxystrobin, propiconazole, proquinazid, prothioconazole, pyridaclomethyl (Registration No. 1358061-55-8), pyraclostrobin, pyrapropoin (Registration No. 1803108-03-3), pyrimethanil, sedaxane spiroxamine, sulfur, tebuconazole, thiophanate-methyl, trifloxystrobin, zoxamide, α-(1-chlorocyclohexane) cyclopropyl)-α-[2-(2,2-dichlorocyclopropyl)ethyl]-1H-1,2,4-triazole-1-ethanol, N-[2-(2,4-dichlorophenyl)-2-methoxy-1-methylethyl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, 3-(difluoromethyl)-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-1-methyl-1H-pyrazole-4-carboxamide, 1-[4-[4-[5R-(2,6-difluorophenyl)-4,5-Dihydro-3-isoxazolyl)-2-thiazolyl]-1-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-ethanone, 1,1-dimethylethyl N-[6-[[[[(1-methyl-1H-tetrazol-5-yl)phenylmethylene]amino]oxy]methyl]-2-pyridinyl]-carbamate, 5-fluoro-2-[(4-fluorophenyl)methoxy]-4-pyrimidinamine, (αS)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-4-isoxazolyl]-3-pyridinemethanol, rel-1-[[(2R,3S)-3-(2-chloro- and a component (b) compound selected from rel-2-[[(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-2-oxiranyl]methyl]-1H-1,2,4-triazole, rel-2-[[(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-2-oxiranyl]methyl]-1,2-dihydro-3H-1,2,4-triazole-3-thione, and rel-1-[[(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)-2-oxiranyl]methyl]-5-(2-propen-1-ylthio)-1H-1,2,4-triazole (i.e., as component (b) in the composition).

[0345] Generally, for better control of plant diseases caused by fungal plant pathogens (e.g., lower use rates or a wider spectrum of controlled plant pathogens) or for resistance management, preferred are combinations of components (a1) and (a2) with the following groups: azoxystrobin, benzovindiflupyr, bixafen, boscalid, carbendazim, chlorothalonil, copper sulfate, cymoxanil, cyproconazole, difenoconazole, dimetamorph, dimoxystrobin, epoxiconazole, fenpropimorph, flurylpicoxamide, fludioxonil, fluindapyr, fluquinconazole, flupicolide, fluoxast and a mixture with a fungicidal compound selected from the group consisting of robin, flutriafol, fluxapyroxad, impilfluxam, ipfentrifluconazole, iprodione, isoflucipram, kresoxim-methyl, mancozeb, metalaxyl, mefentrifluconazole, metconazole, metominostrobin, picoxystrobin, prothioconazole, pydiflumetofen, pyraclostrobin, pyrametostrobin, pyroxystrobin, pyriophenone, sedaxane, silthiofam, tebuconazole, thiabendazole, thiophanate-methyl, trifloxystrobin and triticonazole.

[0346] In the fungicidal compositions of the present invention, components (a1) and (a2) and component (b) are present in fungicidally effective amounts. The weight ratio of components (a1) and / or (a2) to component (b) (i.e., one or more additional fungicidal compounds) is generally from about 1:3000 to about 3000:1, more typically from about 1:500 to about 500:1. Of note are compositions in which the weight ratio of components (a1) and / or (a2) to component (b) is from about 125:1 to about 1:125. Of particular note are compositions in which the weight ratio of components (a1) and / or (a2) to component (b) is from about 25:1 to about 1:25 or from about 5:1 to about 1:5. Those skilled in the art can easily determine by simple experimentation the weight ratios and application rates of the fungicidal compounds required for the desired range of fungicidal protection and control. It will be apparent that the inclusion of additional fungicidal compounds in component (b) can expand the spectrum of plant diseases controlled beyond that controlled by component (a1) and / or component (a2) alone. Furthermore, Tables A1, B1, and C1 provide exemplary weight ratios for combinations of fungicidal compounds of the present invention. Additionally, Table B1 provides typical, more typical, and most typical ranges for ratios involving particular fungicidal compounds in component (b).

[0347] In the fungicidal compositions of the present invention, components (a1) and (a2) are present in synergistically effective amounts. The weight ratio of components (a1) to (a2) is generally about 1:3000 to about 3000:1, more typically about 1:500 to about 500:1. Of note are compositions in which the weight ratio of components (a1) to (a2) is about 125:1 to about 1:125. Of particular note are compositions in which the weight ratio of components (a1) to (a2) is about 25:1 to about 1:25 or about 5:1 to about 1:5.

[0348] In some embodiments, component (a1) and component (a2) are at least about 30:1, about 29:1, about 28:1, about 27:1, about 26:1, about 25:1, about 24:1, about 23:1, about 22:1, about 21:1, about 20:1, about 19:1, about 18:1, about 17:1, about 16:1, about 15:1, about 14:1, about 13:1, about 12:1, about 11:1, about 10:1, about 9:1, about 8:1, about 7:1, about 6:1, about 5:1, about 4:1, about 3:1, about 2:1, about 1.75:1, about 1.5:1, about 1.2 5:1, or in the range of about 1:1 to about 1:2, about 1:3, about 1:4, about 1:5, about 1:6, about 1:7, about 1:8, about 1:9, about 1:10, about 1:11, about 1:12, about 1:13, about 1:14, about 1:15, about 1:16, about 1:17, about 1:18, about 1:19, about 1:20, about 1:21, about 1:22, about 1:23, about 1:24, about 1:25, about 1:26, about 1:27, about 1:28, about 1:29, or about 1:30.

[0349] As mentioned above, the present invention includes an embodiment in which, in a composition comprising components (a1), (a2), and (b), component (b) comprises at least one fungicidal compound selected from (b1) to (b54). Of particular note are compositions of the present invention in which component (b) has a different site of action from components (a1) and / or (a2). In certain instances, combination with at least one other fungicidal compound having a similar control spectrum but a different site of action is particularly advantageous in terms of resistance management. Thus, the composition of the present invention can advantageously contain at least one fungicidally active compound selected from the group consisting of the above (b1) to (b54), which has a similar control spectrum but a different site of action from components (a1) and / or (a2).

[0350] The composition of components (a1) and (a2), or the composition of components (a1) and (a2) with component (b), can be further mixed with one or more other biologically active compounds or agents, including insecticides, nematicides, fungicides, acaricides, herbicides, herbicide antidotes, growth regulators, such as insect molting inhibitors and root stimulators, chemical hemostats, semi-chemicals, repellents, attractants, pheromones, feeding stimulants, plant nutrients, other biologically active compounds, or insect pathogenic bacteria, viruses, or fungi, to form multi-component insecticides that provide an even broader spectrum of agricultural protection. Thus, the present invention also relates to a composition comprising a fungicidally effective amount of components (a1) and (a2), or a mixture of components (a1) and (a2) with component (b), and a biologically effective amount of at least one additional biologically active compound or agent, which may further comprise at least one surfactant, solid diluent, or liquid diluent. Other biologically active compounds or agents can also be formulated separately in a composition that includes at least one of a surfactant, a solid diluent, or a liquid diluent. With respect to the compositions of the present invention, one or more other biologically active compounds or agents can be formulated with one or both of components (a1) and (a2) and (b) to form a premix, or one or more other biologically active compounds or agents can be formulated separately from components (a1) and (a2) and (b), and the formulations can be combined together (e.g., in a spray tank) prior to application or alternatively applied sequentially.

[0351] Examples of such biologically active compounds or agents that can be formulated together with the composition of component (a1) and component (a2) or the composition of component (a1) and component (a2) with component (b) include insecticides such as abamectin, acephate, acequinocyl, acetamiprid, acrinathrin, acinonapyr, afidopiropen, amidoflumet, amitraz, avermectin, azadirachtin, azinphos-methyl, benfuracarb, bensultap, benzpirimoxan, bifenthrin, kappa-bifenthrin, bifenazate, bistrifluron, boronate, benzophenone, benzophenone-1, benzophenone-2, benzophenone-3, benzophenone-4, benzophenone-5, benzophenone-6, benzophenone-7, benzophenone-8, benzophenone-9, benzophenone-11, benzophenone-12, benzophenone-13, benzophenone-14, benzophenone-15, benzophenone-16, benzophenone-17, benzophenone-18, benzophenone-19, benzophenone-20, benzophenone-21, benzophenone-22, benzophenone-23, benzophenone-24, benzophenone-25, benzophenone-26, benzophenone-27, benzophenone-28, benzophenone-29, benzophenone-30, benzophenone-31, benzophenone-32, benzophenone-33, benzophenone-34, benzophenone-35, benzophenone-36, benzophenone-37, benzophenone-38, benzophenone-39, benzophenone-40, benzophenone-41, benzophenone-42, benzophenone-43, benzo late, brofuranilide, buprofezin, cadusafos, carbaryl, carbofuran, cartap, carzol, chlorantraniliprole, chlorfenapyr, chlorfluazuron, chlorprallethrin, chlorpyrifos, chlorpyrifos-e, chlorpyrifos-methyl, chromafenozide, clofentezine, chlorprallethrin, clothianidin, cyantraniliprole, cyclaniliprole, cycloprothrin, cyclooxapride, cyenopyrafen, cyflumetofen, cyfluthrin, beta-cyfluthrin, sialodiamide, sialothrin , gamma-sialothrin, lambda-sialothrin, cypermethrin, alpha-cypermethrin, zeta-cypermethrin, cyromazine, deltamethrin, diafenthiuron, diazinon, dichloromezothiaz, dieldrin, diflubenzuron, dimefluthrin, dimehypo, dimethoate, dipropylidaz, dinotefuran, diofenolan, emamectin, emamectin benzoate, endosulfan, esfenvalerate, ethiprole, etofenprox, epsilon-metofluthrin, etoxazole, fenbutatin oxide, phenbutan Nitrothion, fenothiocarb, fenoxycarb, fenpropathrin, fenvalerate, fipronil, flometoquin, flonicamid, fluazaindolizine, flubendiamide, flucythrinate, flufenerim, flufenoclon, flufenoxystrobin, fluensulfone, fluhexafon, fluopyram, flupiprole, flupyradifurone, flupirimine, fluvalinate, tau-fluvalinate, fluxamethamide, fonofos, formetanate, fosthiazate, gamma-cyhalothrin, halofenozide, heptafluthrin,Hexaflumuron, hexythiazox, hydramethylnon, imidacloprid, indoxacarb, insecticidal soap, isofenphos, isocycloceram, kappa-tefluthrin, lambda-cyhalothrin, lufenuron, malathion, meperfluthrin, metaflumizone, metaldehyde, methamidophos, methidathion, methiocarb, methomyl, methoprene, methoxychlor, metofluthrin, methoxyfenozide, epsilon-metof Lutrin, epsilon-momfluorotrin, monocrotophos, monofluorotrin, nicotine, nitenpyram, nithiazine, novaluron, noviflumuron, oxamyl, oxazosulfil, parathion, parathion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos, profluthrin, propargite, protrifenbut, piflubumid, pymetrozine, pyraflupro ru, pyrethrins, pyridaben, pyridalyl, pyrifluquinazon, pyriminostrobin, pyriprole, pyriproxyfen, rotenone, ryanodine, silaflufen, spinetoram, spinosad, spirodiclofen, spiromesifen, spiropydione, spirotetramat, sulprofos, sulfoxaflor, tebufenozide, tebufenpyrad, teflubenzuron, tefluthrin, kappa-tefluthrin, terbufos, tetrac lontraniliprole, tetrachlorvinphos, tetramethrin, tetramethylfluthrin, tetraniliprole, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, thioxazaphen, tolfenpyrad, tralomethrin, triazamate, trichlorfon, triflumezopyrim, triflumuron, cyclopyrazoflurane, zeta-cypermethrin, Bacillus thuringiensis delta-endotoxin, entomopathogenic bacteria, entomopathogenic viruses, or entomopathogenic fungi.

[0352] In one embodiment, biological agents for admixture with the compounds of the present disclosure include entomopathogenic bacteria, such as Bacillus thuringiensis and encapsulated delta-endotoxin of Bacillus thuringiensis, e.g., MVP® and MVPII® bioinsecticides prepared by the CellCap® process (CellCap®, MVP®, and MVPII® are trademarks of Mycogen Corporation, Indianapolis, Indiana, USA); entomopathogenic fungi, such as green muscardine fungi; and entomopathogenic viruses (both naturally occurring and genetically modified), such as baculoviruses, nucleopolyhedroviruses (NPVs), e.g., Helicoverpa zea nucleopolyhedrovirus (HzNPV), Anagrapha falcifera (Anagrapha falcifera), and entomopathogenic fungi (e.g., entomopathogenic fungi). falcifera nucleopolyhedrovirus (AfNPV); and granulosis viruses (GV), such as codling moth (Cydia pomonella) granulosis virus (CpGV).

[0353] General references for these agricultural protection agents (i.e. insecticides, fungicides, nematicides, acaricides, herbicides and biological agents) include The Pesticide Manual, 13th Edition, CDS Tomlin, Ed., British Crop Protection Council, Farnham, Surrey, UK, 2003 and The BioPesticide Manual, 2nd Edition, L.G. Copping, Ed., British Crop Protection Council, Farnham, Surrey, UK, 2001.

[0354] For embodiments in which one or more invertebrate pest control compounds are used, the weight ratio of these compounds (total) to the components (a1) and (a2) compounds is typically about 1:3000 to about 3000:1. Of note are weight ratios of about 1:300 to about 300:1 (e.g., ratios of about 1:30 to about 30:1). Those skilled in the art can readily determine by simple experimentation the biologically effective amount of active ingredient required to achieve the desired spectrum of biological activity.

[0355] Component (a1) and component (a2) compounds and / or component (b) compounds and / or combinations thereof with one or more other biologically active compounds or agents can be applied to plants genetically engineered to express proteins toxic to invertebrate pests (such as Bacillus thuringiensis delta-endotoxins). The effects of exogenously applied components (a1) and (a2) of the invention, alone or in combination with component (b), can be synergistic with the expressed toxin protein.

[0356] Of note are combinations or compositions comprising components (a1) and (a2) or components (a1) and (a2) and (b) described in the Summary of the Invention, which further comprise at least one invertebrate pest control compound or agent (e.g., an insecticide, acaricide). Of particular note are compositions comprising components (a1) and (a2) and at least one (i.e., one or more) invertebrate pest control compound or agent, which can then be combined with component (b) to provide a composition comprising components (a1) and (a2) and (b) and one or more invertebrate pest control compounds or agents. Alternatively, a biologically effective amount of a composition comprising components (a1) and (a2) and at least one invertebrate pest control agent can be applied to a plant or plant seed (directly or through the environment of the plant or plant seed) without first mixing with component (b) to protect the plant or plant seed from diseases caused by fungal pathogens and damage caused by invertebrate pests.

[0357] Of note, in addition to component (a1) and component (a2), alone or in combination with component (b), are abamectin, acetamiprid, acrinathrin, acinonapyr, afidopiropen, amitraz, avermectin, azadirachtin, benfuracarb, bensultap, bifenthrin, buprofezin, brofuranilide, cadusafos, carbaryl, cartap, chlorantraniliprole, chlorprallethrin, chlorfenapyr, chlorpyrifos, clothianidin, cyantraniliprole, cyclaniliprole, cycloprothrin, cyfluthrin, beta- Cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, zeta-cypermethrin, cyromazine, deltamethrin, dieldrin, dinotefuran, diofenolan, emamectin, endosulfan, epsilon-metofluthrin, esfenvalerate, ethiprole, etofenprox, etoxazole, fenitrothion, fenothiocarb, fenoxycarb, fenvalerate, fipronil, flometoquin, fluxamethamide, flonicamid, flubendiamide, flubendiamide Ensulfone, flufenoxuron, flufenoxystrobin, flufensulfon, flupiprole, flupirimine, flupyradifurone, fluvalinate, formetanate, fosthiazate, gamma-cyhalothrin, heptafluthrin, hexaflumuron, hydramethylnon, imidacloprid, indoxacarb, isocycloceram, kappa-tefluthrin, lambda-cyhalothrin, lufenuron, meperfluthrin, metaflumizone, methiodicarb, methomyl, methoprene, methoxyfenozide, mesofluthrin, monofluorothrin, nitenpi Ram, nithiazine, novaluron, oxamyl, piflubumid, pymetrozine, pyrethrins, pyridaben, pyridalyl, pyriminostrobin, pyriproxyfen, ryanodine, spinetoram, spinosad, spirodiclofen, spiromesifen, spirotetramat, sulfoxaflor, tebufenozide, tetramethrin, tetramethylfluthrin, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tralomethrin, triazamate, triflumezopyrim, triflumuron, cyclopyrazoflurane, zeta-cypermethrin,The composition of the present invention comprises at least one invertebrate pest control compound or agent selected from the group consisting of Bacillus thuringiensis delta-endotoxin, all strains of Bacillus thuringiensis, and all strains of nucleopolyhedrosis virus.

[0358] In certain cases, the combination of component (a1) and component (a2) of the present invention, alone or in mixture with component (b), with other biologically active (especially fungicidal) compounds or agents (i.e., active ingredients) can achieve a greater than additive effect (i.e., a synergistic effect).While ensuring effective pest control, it is always desirable to reduce the amount of active ingredient released into the environment.If the enhancing effect of the fungicidal active ingredient occurs at an application rate that provides an agriculturally satisfactory level of fungus control, such a combination can be advantageous in terms of reducing crop production costs and reducing environmental impact.

[0359] Compositions containing components (a1) and (a2) useful for seed treatment can further contain bacteria and fungi capable of providing protection from the harmful effects of plant pathogenic fungi or bacteria and / or soil-borne animals, such as nematodes. Nematicidal bacteria can include, but are not limited to, Bacillus firmus, Bacillus cereus, Bacillus subtilis, and Pasteuria penetrans. A suitable Bacillus firmus strain is the CNCM I-1582 (GB-126) strain, commercially available under the trademark BioNem™. A suitable Bacillus cereus strain is the NCMM I-1592 strain. Both Bacillus strains are disclosed in U.S. Patent No. 6,406,690. Other suitable bacteria that exhibit nematicidal activity include B. amyloliquefaciens IN937a and B. subtilis strain GB03. Bacteria that exhibit fungicidal properties may include, but are not limited to, B. pumilus strain GB34. Nematicidal fungi may include, but are not limited to, Myrothecium verrucaria, Paecilomyces lilacinus, and Purpureocillium lilacinum.

[0360] Seed treatments can also include one or more naturally occurring nematicides, such as elicitor proteins called harpins, which have been isolated from certain bacterial plant pathogens, such as fire blight (Erwinia amylovora). One example is Harpin-N-Tek seed treatment technology, available as N-Hibit™ Gold CST.

[0361] Seed treatments may also include one or more species of microsymbiotic nitrogen-fixing bacteria, such as legume nodulating bacteria (Bradyrhizobium japonicum). These inoculants can optionally include one or more lipochitooligosaccharides (LCOs), which are nodulation factors produced by rhizobia at the initiation of nodulation on legume roots. For example, Optimize® brand seed treatment technology incorporates LCO Promoter Technology™ in combination with the inoculant.

[0362] Seed treatments can also include one or more isoflavones, which can increase the level of root colonization by mycorrhizal fungi. Mycorrhizal fungi improve plant growth by enhancing root uptake of nutrients such as water, sulfate, nitrate, phosphate, and metals. Examples of isoflavones include, but are not limited to, genistein, biochanin A, formononetin, daidzein, glycitein, hesperetin, naringenin, and pratensein. Formononetin is available as an active ingredient in mycorrhizal inoculant products such as PHC Colonize® AG.

[0363] The seed treatment may also include one or more plant activators that induce systemic acquired resistance in plants after contact with pathogens. One example of a plant activator that induces such a protective mechanism is acibenzolar-S-methyl.

[0364] In the present fungicidal compositions, components (a1) and (a2) can act synergistically with the additional fungicidal compound of component (b) to provide beneficial results such as broadening the spectrum of plant diseases controlled, extending the duration of preventative and therapeutic protection, and inhibiting the growth of resistant fungal pathogens. In certain embodiments, the present invention provides compositions comprising ratios of components (a1) and (a2) and component (b) that are particularly useful for controlling certain fungal diseases (such as Alternaria solani, wheat powdery mildew (Blumeria graminis f.sp. tritici), Botrytis cinerea, wheat leaf rust (Puccinia recondita f.sp. tritici), Rhizoctonia solani, Septoria nodorum, and Septoria tritici).

[0365] Also, mixtures of fungicides can provide significantly better disease control than would be predicted based on the activity of the individual components. This synergy has been described as "the cooperative action of two components of a mixture whose total effect is greater or longer lasting than the sum of the effects of the two (or more) components taken independently" (see PM L Tames, Neth. J. Plant Pathology 1964, 70, 73-80). In methods of providing synergistic plant disease control from combinations of active ingredients (e.g., fungicidal compounds) applied to plants or seeds, the active ingredients are applied in synergistic weight ratios and synergistic (i.e., synergistically effective) amounts. The measure of disease control, suppression, and prevention cannot exceed 100%. Therefore, to achieve substantial synergistic effect, it is typically necessary to use active ingredient dosages that provide a significantly less than 100% effect when the active ingredients are used separately, and to take into account the possibility of increased synergistic effect, so that their additive effect is substantially less than 100%.On the other hand, if the dosage of the active ingredients is too low, even if there is a synergistic advantage, they may not show much activity in the mixture.Those skilled in the art can easily identify and optimize the weight ratio and dosage (i.e., amount) of fungicidal compounds that produce synergistic effect through simple experiments.

[0366] Synergistic effect always exists when the effect of the combination of active ingredients is greater than the sum of the effects of each ingredient alone.Therefore, synergistic combination is a combination of active ingredients that has an effect greater than the sum of the effects of each active ingredient alone, and synergistically effective amount is the effective amount of synergistic combination.Well-known methods for determining whether synergistic effect exists include Colby method, Tames method, and Wadley method, all of which are described below.Any one of these methods can be used to determine whether synergistic effect exists between compound A and B.

[0367] In the Colby method, also known as the Limpels method, the expected effect E of a given combination of active ingredients follows the so-called Colby formula. According to Colby, the expected effect of active ingredients A+B using p+q ppm of active ingredients is:

number

[0368] The Tammes method uses a graphic representation to determine whether a synergistic effect exists. See "Isoboles, a graphic representation of synergism in pesticides," Netherlands Journal of Plant Pathology, 70 (1964) pp. 73-80.

[0369] The Wadley method combines the observed EC50 value (i.e., the concentration that provides the 50% control) obtained from experimental data using a dose-response curve and the formula:

number

[0370] Without further elaboration, it is believed that one skilled in the art can, using the preceding description, utilize the present invention to its fullest extent. However, the following examples are to be construed as merely illustrative, and not limiting of the disclosure in any way. [Example]

[0371] Biological Examples of the Invention The following tests demonstrate the control efficacy of the compositions (i.e., mixtures) of the present invention against specific fungal pathogens. In particular, the effectiveness of the compositions was evaluated against pathogen strains that have been identified as susceptible or resistant biotypes and that have been associated with failure of control against previously effective fungicides, such as those identified by FRAC.

[0372] Strains of Zymoseptoria tritici (synonym Septoria tritici) expressing one or more gene mutations used for inoculation in the following studies were obtained as follows:

[0373] Zymoseptoria tritici isolate IPO323 (an epitype of Septoria tritici Desm.) was obtained from the Westerdijk Fungal Biodiversity Institute (CBS, Netherlands), an International Depository Authority (IDA) under the regulations of the Budapest Treaty on the International Recognition of the Deposit of Microorganisms for the Purposes of Patent Procedure. The isolate was deposited in the CBS library on July 5, 1981, under the reference number CBS 115943.

[0374] Zymoseptoria tritici strains TriR6 and TriR10 (two phenotypes from the TriMR group expressing CYP51 mutations) were obtained from INRAE ​​(French National Institute for Agriculture, Food and Environment). All isolates were maintained in glycerol at -80°C and allowed to reach room temperature before use in the study. Isolates were used after a single transfer onto Petri dishes.

[0375] The TriMR group encompasses several different phenotypes, each with known fungicide resistance factors. For more information on phenotypic categories and their fungicide resistance factors, see: Evolution of resistance to fungicides in populations of Mycosphaerella graminicola: emergence of new phenotypes highly resistant to DMIs, Conference: EPPO workshop on Azole fungicide and Septoria leaf blotch control, December 2010; Leroux et al., Pest Management Science, 2007, 63, 688-98; and Walker, Pest Management Science, 2011, 67, 44-59.

[0376] Strains identified in the following tests as 20, 30, 39, and 97 are field isolates with target site mutations that confer reduced susceptibility to SDHI fungicides. The isolates were recovered and characterized in 2021 during resistance monitoring in Europe. The table below summarizes the mutations detected for each of these strains as well as the country of origin of the isolate.

[0377] [Table 4]

[0378] The general protocol for preparing the test compositions used in Tests A-G is as follows: Technical grade fluindapyr was prepared and formulated as an emulsifiable concentrate (100 EC). Fenpicoxamid was obtained as a formulated product (commercially available as Questar™). The product was dispersed in a sufficient amount of water to achieve the desired concentration; no organic solvents or surfactants were added to the suspension. The resulting test mixture was then sprayed at 250 L / ha using a tunnel sprayer for use in Tests A-H. Application rates were 50 and 150 grams per hectare for fluindapyr and 33.3 and 100 grams per hectare for fenpicoxamid.

[0379] [Table 5]

[0380] The test results for Tests A-G are shown in the tables below. The results in each table correspond to a series of ratings conducted simultaneously. In each table, a rating of 100 indicates 100% disease control, and a rating of 0 indicates no disease control (compared to untreated controls). The column labeled "Observed Effect" shows the average observed results from independent tests conducted on individual plants (the number of replicates is shown below). The "Predicted Effect" column shows the predicted value for each treatment mixture using the Colby equation.

[0381] Test A Test compositions were sprayed onto 6-day-old wheat seedlings. The next day, the seedlings were inoculated with a spore suspension of Zymoseptoria tritici (strain IPO323) (the causal agent of wheat leaf blotch (Septoria tritici blotch)) and incubated in a saturated atmosphere at 20°C for 48 hours, then transferred to a growth chamber at 20°C for 21 days, after which time the disease was visually assessed. The test results provided in Table A below are the average of four tests, each with four replicates (i.e., pots) per composition, each containing five plants.

[0382] Table A Observed and predicted efficacy of Composition 1 and Composition 2 used alone and mixtures in controlling wheat leaf blotch (Septoria tritici blotch) caused by Zymoseptoria tritici (strain IPO323)

[0383] [Table 6]

[0384] Test B The test suspension was sprayed onto 6-day-old wheat seedlings. The next day, the seedlings were inoculated with a spore suspension of Zymoseptoria tritici (strain TriR6) (the causal agent of wheat leaf blotch (Septoria tritici blotch)) and incubated in a saturated atmosphere at 20°C for 48 hours, then transferred to a growth chamber at 20°C for 21 days, after which time the disease was visually assessed. The test results provided in Table B below are the average of two tests, each with four replicates (i.e., pots) per composition, each containing five plants.

[0385] Table B Observed and predicted efficacy of Composition 1 and Composition 2 used alone and in mixtures in controlling wheat leaf blotch (Septoria tritici blotch) caused by Zymoseptoria tritici (strain TriR6)

[0386] [Table 7]

[0387] Test C The test suspension was sprayed onto 6-day-old wheat seedlings. The next day, the seedlings were inoculated with a spore suspension of Zymoseptoria tritici (strain TriR10) (the causal agent of wheat leaf blotch) and incubated in a saturated atmosphere at 20°C for 48 hours, then transferred to a growth chamber at 20°C for 21 days, after which time the disease was visually assessed. The test results provided in Table C below are the average of two tests, each with four replicates (i.e., pots) per composition, each containing five plants.

[0388] Table C Observed and predicted efficacy of Composition 1 and Composition 2 used alone and in mixtures in controlling wheat leaf blotch (Septoria tritici blotch) caused by Zymoseptoria tritici (strain TriR10)

[0389] [Table 8]

[0390] Test D The test suspension was sprayed onto 6-day-old wheat seedlings. The next day, the seedlings were inoculated with a spore suspension of Zymoseptoria tritici (strain 20, harboring mutation N86S), the causal agent of wheat leaf blotch (septoria tritici blotch), and incubated in a saturated atmosphere at 20°C for 48 hours, then transferred to a growth chamber at 20°C for 21 days, after which time the disease was visually assessed. The test results, presented in Table D below, are the average of three tests, each with four replicates (i.e., pots) per composition, each containing five plants.

[0391] Table D Observed and predicted efficacy of Composition 1 and Composition 2 used alone and in mixtures in controlling Septoria Tritici Blotch caused by Zymoseptoria tritici (strain 20, carrying the N86S mutation)

[0392] [Table 9]

[0393] Test E The test suspension was sprayed onto 6-day-old wheat seedlings. The next day, the seedlings were inoculated with a spore suspension of Zymoseptoria tritici (strain 30, harboring mutations F23S, I29V, N33T, N34T, and H152R) (the causal agent of wheat leaf blotch (Septoria tritici blotch)) and incubated in a saturated atmosphere at 20°C for 48 hours, then transferred to a growth chamber at 20°C for 21 days, after which time the disease was visually assessed. The test results, presented in Table E below, are the average of three tests, each with four replicates (i.e., pots) per composition, each containing five plants.

[0394] Table E Observed and predicted efficacy of Composition 1 and Composition 2 used alone and in mixtures in controlling Septoria Tritici Blotch caused by Zymoseptoria tritici (strain 30, harboring mutations F23S, I29V, N33T, N34T, and H152R)

[0395] [Table 10]

[0396] Test F The test suspension was sprayed onto 6-day-old wheat seedlings. The next day, the seedlings were inoculated with a spore suspension of Zymoseptoria tritici (strain 39, harboring mutation H152R), the causal agent of wheat leaf blotch (Septoria tritici blotch), and incubated in a saturated atmosphere at 20°C for 48 hours, then transferred to a growth chamber at 20°C for 21 days, after which time the disease was visually assessed. The test results, provided in Table F below, are the average of three tests, each with four replicates (i.e., pots) per composition, each containing five plants.

[0397] Table F Observed and predicted efficacy of Composition 1 and Composition 2 used alone and in mixtures in controlling Septoria Tritici Blotch caused by Zymoseptoria tritici (strain 39, carrying the mutation H152R)

[0398] [Table 11]

[0399] Test G The test suspension was sprayed onto 6-day-old wheat seedlings. The next day, the seedlings were inoculated with a spore suspension of Zymoseptoria tritici (strain 97, harboring mutation T79N), the causal agent of wheat leaf blotch (Septoria tritici blotch), and incubated for 48 hours in a saturated atmosphere at 20°C. They were then transferred to a growth chamber at 20°C for 21 days, after which time they were visually assessed for disease. The test results, presented in Table G below, are the average of three tests, each with four replicates (i.e., pots) per composition, each containing five plants.

[0400] Table G Observed and predicted efficacy of Composition 1 and Composition 2 used alone and in mixtures in controlling Septoria Tritici Blotch caused by Zymoseptoria tritici (strain 97, carrying mutation T79N)

[0401] [Table 12]

[0402] The general protocol for preparing the test compositions used in Tests H-N is as follows: Benzovindiflupyr was obtained as a formulated product (commercially available as ELATUS® PLUS). Fenpicoxamid was as described above for Composition 2. The product was dispersed in a sufficient amount of water to achieve the desired concentration; no organic solvents or surfactants were added to the suspension. The resulting test mixture was then sprayed at 250 L / ha using a tunnel sprayer for use in Tests H-N. Application rates were 25 and 75 grams per hectare for benzovindiflupyr and 33.3 and 100 grams per hectare for fenpicoxamid.

[0403] [Table 13]

[0404] The test results for trials H-N are shown in the tables below. The results in each table correspond to a series of ratings conducted simultaneously. In each table, a rating of 100 indicates 100% disease control, and a rating of 0 indicates no disease control (compared to untreated controls). The column labeled "Observed Effect" shows the average observed results from independent tests conducted on individual plants (the number of replicates is shown below). The "Predicted Effect" column shows the predicted value for each treatment mixture using the Colby equation.

[0405] Test H The test suspension was sprayed onto 6-day-old wheat seedlings. The next day, the seedlings were inoculated with a spore suspension of Zymoseptoria tritici (strain IPO323) (the causal agent of wheat leaf blotch (Septoria tritici blotch)) and incubated for 48 hours in a saturated atmosphere at 20°C, then transferred to a growth chamber at 20°C for 21 days, after which time the disease was visually assessed. The test results, provided in Table H below, are for a single test; each test had four replicates (i.e., pots) per composition, and each replicate (i.e., pot) contained five plants.

[0406] Table H Observed and predicted efficacy of Composition 3 and Composition 2 used alone and in mixtures in controlling wheat leaf blotch (Septoria tritici blotch) caused by Zymoseptoria tritici (strain IPO323)

[0407] [Table 14]

[0408] Test I The test suspension was sprayed onto 6-day-old wheat seedlings. The next day, the seedlings were inoculated with a spore suspension of Zymoseptoria tritici (TriR6 mutant strain), the causal agent of wheat leaf blotch (Septoria tritici blotch), and incubated in a saturated atmosphere at 20°C for 48 hours. They were then transferred to a growth chamber at 20°C for 21 days, after which time they were visually assessed for disease. The test results, provided in Table I below, are for a single test; each test had four replicates (i.e., pots) per composition, and each replicate (i.e., pot) contained five plants.

[0409] Table I Observed and predicted efficacy of Composition 3 and Composition 2 used alone and in mixtures in controlling wheat leaf blotch (Septoria tritici blotch) caused by Zymoseptoria tritici (TriR6 mutant strain)

[0410] [Table 15]

[0411] Exam J The test suspension was sprayed onto 6-day-old wheat seedlings. The next day, the seedlings were inoculated with a spore suspension of Zymoseptoria tritici (mutant TriR10 strain), the causal agent of wheat leaf blotch (Septoria tritici blotch), and incubated in a saturated atmosphere at 20°C for 48 hours, then transferred to a growth chamber at 20°C for 21 days, after which time the disease was visually assessed. The test results, provided in Table J below, are for a single test; each test had four replicates (i.e., pots) per composition, and each replicate (i.e., pot) contained five plants.

[0412] Table J Observed and predicted efficacy of Composition 3 and Composition 2 used alone and in mixtures in controlling wheat leaf blotch (Septoria tritici blotch) caused by Zymoseptoria tritici (TriR10 mutant strain)

[0413] [Table 16]

[0414] Exam K The test suspension was sprayed onto 6-day-old wheat seedlings. The next day, the seedlings were inoculated with a spore suspension of Zymoseptoria tritici (strain 20, harboring mutation N86S), the causal agent of wheat leaf blotch (septoria tritici blotch), and incubated for 48 hours in a saturated atmosphere at 20°C. They were then transferred to a growth chamber at 20°C for 21 days, after which time they were visually assessed for disease. The test results, provided in Table K below, are for a single test; each test had four replicates (i.e., pots) per composition, and each replicate (i.e., pot) contained five plants.

[0415] Table K Observed and predicted efficacy of Composition 3 and Composition 2 used alone and in mixtures in controlling Septoria Tritici Blotch caused by Zymoseptoria tritici (strain 20, carrying mutation N86S)

[0416] [Table 17]

[0417] Test L The test suspension was sprayed onto 6-day-old wheat seedlings. The next day, the seedlings were inoculated with a spore suspension of Zymoseptoria tritici (strain 30, harboring mutations F23S, I29V, N33T, N34T, and H152R) (the causal agent of wheat leaf blotch (Septoria tritici blotch)) and incubated in a saturated atmosphere at 20°C for 48 hours, then transferred to a growth chamber at 20°C for 21 days, after which time the disease was visually assessed. The test results, provided in Table L below, are for a single test; each test had four replicates (i.e., pots) per composition, and each replicate (i.e., pot) contained five plants.

[0418] Table L Observed and predicted efficacy of Composition 3 and Composition 2 used alone and in mixtures in controlling Septoria Tritici Blotch caused by Zymoseptoria tritici (strain 30, harboring mutations F23S, I29V, N33T, N34T, and H152R)

[0419] [Table 18]

[0420] Test M The test suspension was sprayed onto 6-day-old wheat seedlings. The next day, the seedlings were inoculated with a spore suspension of Zymoseptoria tritici (strain 39, harboring mutation H152R), the causal agent of wheat leaf blotch (Septoria tritici blotch), and incubated in a saturated atmosphere at 20°C for 48 hours, then transferred to a growth chamber at 20°C for 21 days, after which time the disease was visually assessed. The test results, provided in Table M below, are for a single test; each test had four replicates (i.e., pots) per composition, and each replicate (i.e., pot) contained five plants.

[0421] Table M Observed and predicted efficacy of Composition 3 and Composition 2 used alone and in mixtures in controlling Septoria Tritici Blotch caused by Zymoseptoria tritici (strain 39, carrying the mutation H152R)

[0422] [Table 19]

[0423] Test N The test suspension was sprayed onto 6-day-old wheat seedlings. The next day, the seedlings were inoculated with a spore suspension of Zymoseptoria tritici (strain 97, harboring mutation T79N), the causal agent of wheat leaf blotch (Septoria tritici blotch), and incubated in a saturated atmosphere at 20°C for 48 hours, then transferred to a growth chamber at 20°C for 21 days, after which time the disease was visually assessed. The test results, provided in Table N below, are for a single test; each test had four replicates (i.e., pots) per composition, and each replicate (i.e., pot) contained five plants.

[0424] Table N Observed and predicted efficacy of Composition 3 and Composition 2 used alone and in mixtures in controlling Septoria Tritici Blotch caused by Zymoseptoria tritici (strain 97, carrying mutation T79N)

[0425] [Table 20]

[0426] The general protocol for preparing the test compositions used in Tests O through Q is as follows: Fluxapyroxad was obtained as a formulated product (commercially available as IMTREX®). Fenpicoxamid was as described above for Composition 2. The product was dispersed in a sufficient amount of water to achieve the desired concentration; no organic solvents or surfactants were added to the suspension. The resulting test mixture was then sprayed at 250 L / ha using a tunnel sprayer for use in Tests O through Q. Application rates were 41.67, 62.5, and 125 grams per hectare for fluxapyroxad and 33.3, 75, and 100 grams per hectare for fenpicoxamid.

[0427] [Table 21]

[0428] Test O The test suspension was sprayed onto 6-day-old wheat seedlings. The next day, the seedlings were inoculated with a spore suspension of Zymoseptoria tritici (strain 20, harboring mutation N86S), the causal agent of wheat leaf blotch (Septoria tritici blotch), and incubated in a saturated atmosphere at 20°C for 48 hours. They were then transferred to a growth chamber at 20°C for 21 days, after which time they were visually assessed for disease. The test results, presented in Table O below, are the average of two tests, each with four replicates (i.e., pots) per composition, each containing five plants.

[0429] Table O Observed and predicted efficacy of Composition 4 and Composition 2 used alone and mixtures in controlling Septoria Tritici Blotch caused by Zymoseptoria tritici (strain 20, carrying mutation N86S)

[0430] [Table 22]

[0431] Test P The test suspension was sprayed onto 6-day-old wheat seedlings. The next day, the seedlings were inoculated with a spore suspension of Zymoseptoria tritici (strain 30, harboring mutations F23S, I29V, N33T, N34T, and H152R) (the causal agent of wheat leaf blotch (Septoria tritici blotch)) and incubated in a saturated atmosphere at 20°C for 48 hours, then transferred to a growth chamber at 20°C for 21 days, after which time the disease was visually assessed. The test results, presented in Table P below, are the average of two tests, each with four replicates (i.e., pots) per composition, each containing five plants.

[0432] Table P Observed and predicted efficacy of Composition 4 and Composition 2 used alone and in mixtures in controlling Septoria Tritici Blotch caused by Zymoseptoria tritici (strain 30, harboring mutations F23S, I29V, N33T, N34T, and H152R)

[0433] [Table 23]

[0434] Test Q The test suspension was sprayed onto 6-day-old wheat seedlings. The next day, the seedlings were inoculated with a spore suspension of Zymoseptoria tritici (strain 97, harboring mutation T79N) (the causal agent of wheat leaf blotch (Septoria tritici blotch)) and incubated in a saturated atmosphere at 20°C for 48 hours, then transferred to a growth chamber at 20°C for 21 days, after which time the disease was visually assessed. The test results, presented in Table Q below, are the average of two tests, each with four replicates (i.e., pots) per composition, each containing five plants.

[0435] Table Q Observed and predicted efficacy of Composition 4 and Composition 2 used alone and in mixtures in controlling Septoria Tritici Blotch caused by Zymoseptoria tritici (strain 97, carrying mutation T79N)

[0436] [Table 24]

Claims

1. (a1) a succinate dehydrogenase inhibitor (SDHI); and (a2) picolinamide, A composition comprising:

2. The SDHI is (a1-a) phenylbenzamide, benodanil, flutolanil, mepronil, phenyloxoethylthiophenamide, isofetamide, pyridinylethylbenzamide, fluopyram, furancarboxamide, fenfuram, oxathiincarboxamide, carboxin and oxycarboxin, thiazolecarboxamide, thifluzamide, pyrazole-4-carboxamide, benzovindiflupyr, bixafen, fluveneteram, fluindapyr, fluxapyroxad, furametpyr, inpirfluxam, Isopyrazam, penflufen, penthiopyrad, sedaxane, N-[2-(2,4-dichlorophenyl)-2-methoxy-1-methylethyl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, N-cyclopropyl-N-benzyl-pyrazolecarboxamide, isoflucipram, N-methoxy-(phenyl-ethyl)-pyrazolecarboxamide, pydiflumetofen, pyridinecarboxamide, boscalid, pyrazinecarboxamide fungicides, and pyraziflumid, and (a1-b) Formula (I): 【Chemistry 1】 [In the formula, R １ , R ２ , R ３ and R ４ are each independently H, C １ ~C ４ Alkyl, C １ ~C ４ Haloalkyl, C ３ ~C ６ Cycloalkyl or C ３ ~C ６ halocycloalkyl, R ５ and R ７ are each independently H, C １ ~C ４ Alkyl or C １ ~C ４ is haloalkyl, R ６ is C １ ~C ４ Alkyl, C １ ~C ４ Haloalkyl, C ３ ~C ６ Cycloalkyl, C ３ ~C ６ Halocycloalkyl, C １ ~C ４ Alkoxy, C １ ~C ４ Haloalkoxy, C １ ~C ４ Alkylthio, or C １ ~C ４ haloalkylthio, R ８ is halo, -OH, -SH, C １ ~C ４ Alkyl, C １ ~C ４ Haloalkyl, C １ ~C ４ Alkoxy, C １ ~C ４ Haloalkoxy, C １ ~C ４ Alkylthio, or C １ ~C ４ haloalkylthio, n is 0 to 3. and aminoindanamides having the structure (a1-c) Combinations of these The composition of claim 1 selected from:

3. The SDHI aminoindanamide of formula (I) has the structure: 【Chemistry 2】 2. The composition of claim 1, wherein the compound is a fluindapyr having the formula:

4. 2. The composition of claim 1, wherein the SDHI is benzovindiflupyr.

5. 2. The composition of claim 1, wherein the SDHI is fluxapyroxad.

6. The picolinamide is 10. The composition of claim 1, wherein (a2-a) is selected from fenpicoxamide, florylpicoxamide, [(1S,2S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, [(1S,2S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl](2S)-2-[[3-(acetoxymethoxy)-4-methoxy-pyridine-2-carbonyl]amino]propanoate, and [(1S,2S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl](2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate.

7. 2. The composition of claim 1, wherein the picolinamide is selected from (a2-a) fenpicoxamide and florylpicoxamide and (a2-b) methallylpicoxamide.

8. 8. The composition of claim 7, wherein the picolinamide is fenpicoxamid.

9. 8. The composition of claim 7, wherein the picolinamide is furoylpicoxamide.

10. 8. The composition of claim 7, wherein the picolinamide is methallyl picoxamide.

11. 2. The composition of claim 1, wherein the SDHI is selected from (a1-a) benzovindiflupyr, fluindapyr, and fluxapyroxad, and the picolinamide is selected from (a2-a) fenpicoxamide and flurylpicoxamide, and (a2-b) methallylpicoxamide.

12. The composition of claim 11, wherein the SDHI is fluindapyr.

13. 12. The composition of claim 11, wherein the picolinamide is fenpicoxamid.

14. (b1) methyl benzimidazole carbamate (MBC) fungicide; (b2) dicarboximide fungicides, (b3) demethylation inhibitor (DMI) fungicides; (b4) phenylamide (PA) fungicides; (b5) amine / morpholine fungicides; (b6) phospholipid biosynthesis inhibitor fungicides, (b7) an additional succinate dehydrogenase inhibitor (SDHI) fungicide; (b8) hydroxy(2-amino-)pyrimidine fungicides, (b9) anilinopyrimidine (AP) fungicides; (b10) N-phenylcarbamate fungicides, (b11) quinone outside inhibitor (QoI) fungicides; (b12) phenylpyrrole (PP) fungicides; (b13) azanaphthalene fungicides, (b14) cellular peroxidation inhibitor fungicides; (b15) melanin biosynthesis inhibitor-reductase (MBI-R) fungicides; (b16a) melanin biosynthesis inhibitor-dehydratase (MBI-D) fungicides; (b16b) melanin biosynthesis inhibitor-polyketide synthase (MBI-P) fungicides; (b17) ketoreductase inhibitor (KRI) fungicides; (b18) squalene-epoxidase inhibitor fungicides, (b19) polyoxin fungicides, (b20) phenylurea fungicides, (b21) quinone inside inhibitor (QiI) fungicides; (b22) benzamide and thiazolecarboxamide fungicides; (b23) enopyranuronic acid antibiotic fungicides, (b24) hexopyranosyl antibiotic fungicides, (b25) glucopyranosyl antibiotics: protein synthesis fungicides, (b26) glucopyranosyl antibiotic fungicides, (b27) cyanoacetamide oxime fungicides, (b28) carbamate fungicides, (b29) oxidative phosphorylation uncoupling fungicides, (b30) organotin fungicides, (b31) carboxylic acid fungicides, (b32) heteroaromatic compound fungicides, (b33) phosphonate fungicides, (b34) phthalamic acid fungicides, (b35) benzotriazine fungicides, (b36) benzene-sulfonamide fungicides, (b37) pyridazinone fungicides, (b38) thiophene-carboxamide fungicides, (b39) Complex I NADH oxidoreductase inhibitor fungicide, (b40) carboxylic acid amide (CAA) fungicides; (b41) tetracycline antibiotic fungicides, (b42) thiocarbamate fungicides, (b43) benzamide fungicides, (b44) microbial fungicides, (b45) quinone outside inhibitor, stigmatellin binding (QoSI) fungicides; (b46) plant extract fungicides, (b47) cyanoacrylate fungicides, (b48) polyene fungicides, (b49) oxysterol binding protein inhibitor (OSBPI) fungicides; (b50) aryl-phenyl-ketone fungicides, (b51) host plant defense-inducing fungicides; (b52) multi-site active fungicides, (b53) biological agents with multiple mechanisms of action; (b54) a fungicide other than the fungicides of component (a1) and component (a2) and components (b1) to (b53), and Salts of compounds (b1) to (b54) The composition of claim 1 further comprising at least one component (b) selected from:

15. 10. The composition of claim 1 and at least one additional component selected from a surfactant, a solid diluent, and a liquid diluent.

16. 10. The composition of claim 1, wherein the SDHI and the picolinamide are present in a ratio of SDHI:picolinamide ranging from about 2:1 to about 1:

1.

17. 2. The composition of claim 1, wherein the SDHI and the picolinamide are present in a ratio of SDHI:picolinamide of 1.5:

1.

18. 10. The composition of claim 1, wherein the SDHI is selected from a suspension concentrate, a capsule suspension, an emulsifiable concentrate, a granule, a wettable granule, and combinations thereof.

19. 10. The composition of claim 1, wherein the picolinamide is selected from a suspension concentrate, a capsule suspension, an emulsifiable concentrate, a granule, a wettable granule, and combinations thereof.

20. 10. A method for protecting a plant or plant seed from disease caused by a fungal pathogen, comprising applying to said plant or plant seed a fungicidally effective amount of the composition of claim 1.

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