Fungicidal compositions

Abstract

A composition suitable for controlling diseases caused by plant pathogens comprising (A) a compound having formula (I), wherein R 1 is H, C(=O)CH3 or C(=O)CH2CH3; and (B) at least one compound selected from compounds known for their fungicidal activity; and a method of controlling diseases on useful plants, especially rust diseases on soybean or cereals.

Description

[0001] This invention relates to novel fungicidal compositions suitable for controlling diseases caused by plant pathogenic fungi, particularly Phakopsorapachyrhizi (the pathogen of Asian soybean rust), and to a method for controlling diseases of useful plants, particularly soybeans.

[0002] As known from WO 2019 / 173665, certain pyridine amide derivatives and mixtures containing said pyridine amide derivatives possess biological activity against plant pathogenic fungi. On the other hand, various fungicides of different chemical classes are well known as plant fungicides for application in a wide range of cultivated plant crops. However, crop tolerance and activity against plant pathogenic fungi do not always meet the needs of agricultural practices in many events and aspects. For example, *Solanum spp.* rust (the pathogen of Asian soybean rust) has become an increasingly important problem in soybean production, causing considerable yield losses. Many conventional fungicides are unsuitable for controlling Asian soybean rust, or their effectiveness against *Solanum spp.* rust is unsatisfactory.

[0003] In light of the aforementioned agricultural practices requiring enhanced crop tolerance and / or increased activity against plant pathogenic fungi (such as *Pseudomonas beanus* rust), this invention provides a novel composition suitable for controlling diseases caused by plant pathogens, comprising:

[0004] (A) Compounds having formula I

[0005]

[0006] Where R 1 It is H, C(=O)CH3 or C(=O)CH2CH3; and

[0007] (B) At least one compound selected from the group consisting of: 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thio-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methylformamidinium, N'-[2-chloro-4-(2-fluorophenoxy)- [5-Methyl-phenyl]-N-ethyl-N-methylformamidinium, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiobenzamide, 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide, and N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide.

[0008] In each case, the compounds of Formula I according to the invention may be in their free form, oxidized form (such as N-oxide), or salt form (e.g., agronomically available salt form).

[0009] N-oxides are the oxidized forms of tertiary amines or nitrogen-containing heteroaromatic compounds. For example, they are described by A. Albini and S. Pietra in their 1991 book, "Heterocyclic N-oxides," published by CRC Press in Boca Raton.

[0010] Preferred compositions comprise: (A) a compound having formula I

[0011]

[0012] Where R 1 It is H, C(=O)CH3 or C(=O)CH2CH3; and

[0013] (B) At least one compound selected from the group consisting of: N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidinium, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiobenzamide, 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide and N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide.

[0014] It has been found that combining component (B) with component (A) unexpectedly and substantially enhances the latter’s antifungal efficacy, and vice versa.

[0015] Furthermore, the methods and uses according to the invention are effective against a wider spectrum of this fungus, and when used alone, the active ingredients of the methods of the invention can combat this fungus.

[0016] Another aspect of the invention relates to a method for controlling diseases caused by plant pathogens on useful plants or their propagation material, the method comprising applying a composition according to the invention to such useful plants, their sites, or their propagation material.

[0017] Preferred methods include applying the composition according to the invention to these useful plants or their sites, more preferably to these useful plants. Further preferred methods include applying the composition according to the invention to the propagation material of these useful plants.

[0018] (B) This invention relates to all stereoisomers having Formula I and mixtures thereof in any ratio.

[0019] Preferred compounds having formula (I) are: (2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propionic acid [(1S,2S)-1-methyl-2-(o-tolyl)propyl] ester (compound A-1.1), according to structure I.1:

[0020]

[0021] as well as

[0022] (2S)-2-[(4-methoxy-3-propanoyloxy-pyridin-2-carbonyl)amino]propionic acid [(1S,2S)-1-methyl-2-(o-tolyl)propyl] ester (compound A-1.2), according to structure I.2:

[0023]

[0024] Compounds A-1.1 and A-1.2 can be advantageously prepared in a manner similar to that outlined in WO 2019 / 173665.

[0025] One or more components (B) of the subject composition are selected from one or more of the following compounds:

[0026] 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thio-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile;

[0027] N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidin;

[0028] N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidin;

[0029] N-Methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiobenzamide;

[0030] 2,2-Difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide; and / or

[0031] N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide.

[0032] These compounds are known to have selective fungicidal activity: 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thio-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile is disclosed in WO2016 / 187201. N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidin is disclosed in WO2017 / 005710. N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidin is disclosed in WO 2016 / 202742. N-Methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiobenzamide has been disclosed in WO 2017 / 211649. 2,2-Difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide has been disclosed in WO 2017 / 076742; and N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide has been disclosed in WO 2015 / 185485.

[0033] Where appropriate, the compounds (B) according to the invention may be in their free form, oxidized form (such as N-oxide), or salt form (e.g., agronomically available salt form).

[0034] Throughout this document, the term "composition" refers to various mixtures or combinations of components (A) and (B), for example, in a single "ready-to-use with water" form, as a combined spray mixture (consisting of separate formulations of individual active ingredient components) (e.g., a "tank mix"), and as a combination of individual active ingredients when applied sequentially (i.e., one after another over a suitably short period of time, such as hours or days). For the purposes of this invention, the order in which components (A) and (B) are applied is not critical.

[0035] The compositions according to the invention have been found to be effective against harmful microorganisms, such as those that cause plant pathogenic diseases, particularly against plant pathogenic fungi and bacteria.

[0036] The compositions according to the invention are particularly effective against plant pathogenic fungi belonging to the following classes: Ascomycetes (e.g., *Aureobasidium*, *Cyclocarya*, *Erythrophagus*, *Pseudomonas*, *Cyclocarya*, *Uncaria*); Basidiomycetes (e.g., *Hemileia*, *Rhizoctonia*, *Laminaria*, *Pseudomonas*, *Ustilago*, *Ustilago*); Deuteromycetes (e.g., *Botrytis*, *Helicobacter*, *Rhizoctonia*, *Fusarium*, *Zymoseptoria*, *Cercospora*, *Alternaria*, *Pyrophagus*, and *Pseudomonas*); Oomycetes (e.g., *Phytophthora*, *Peronospora*, *Pseudomonas*, *Eucomyces*, *Plasmodium*, *Pseudomonas*, *Pseudomonas*, *Pseudomonas*, *Pseudomonas*, *Pseudomonas*, *Pseudomonas*, *Pseudomonas*, *Pseudomonas*).

[0037] According to the present invention, "useful plants" typically include the following plant species: grapevines; cereals, such as wheat, barley, rye, or oats; beets, such as sugar beets or forage beets; fruits, such as pome, drupe, or soft fruits, for example, apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, or blackberries; legumes, such as beans, lentils, peas, or soybeans; oil crops, such as rapeseed, mustard, poppies, olives, sunflowers, coconuts, castor oil plants, cocoa beans, or peanuts; and cucumber-like plants, such as... Gourds, cucumbers, or cantaloupes; fiber plants such as cotton, flax, hemp, or jute; citrus fruits such as oranges, lemons, grapefruits, or tangerines; vegetables such as spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, gourds, or peppers; Lauraceae, such as avocados, cinnamon, or camphor; corn; tobacco; nuts; coffee; sugarcane; tea; vines; hops; durian; bananas; natural rubber plants; turf or ornamental plants such as flowering plants, shrubs, broadleaf trees, or evergreens, such as pines. This list does not represent any restrictions.

[0038] The term "useful plant" should be understood to include useful plants that have developed tolerance to herbicides (like bromuconazole) or herbicide classes (such as HPPD inhibitors, ALS inhibitors, such as flusulfuron, fluprosulfuron, and triflusulfuron, EPSPS (5-enol-pyrovyl-shikimate-3-phosphate-synthase) inhibitors, GS (glutamine synthase) inhibitors, or PPO (protoporphyrinogen oxidase) inhibitors) through conventional breeding or genetic engineering methods. Examples of crops that have been induced to tolerate imidazolinones (e.g., methoxyfenozide) through conventional breeding methods (mutation) are... Summer rapeseed (Carnora). Examples of crops that have been genetically engineered to be resistant to herbicides or herbicides include glyphosate-resistant and glufosinate-resistant maize varieties, marketed under trade names. and Available for commercial purchase.

[0039] The term “useful plant” should be understood to also include useful plants that have been transformed by the use of recombinant DNA technology to enable them to synthesize one or more selectively acting toxins, such as those known to come from toxin-producing bacteria, especially those of the genus Bacillus.

[0040] The term "useful plant" should be understood to also include useful plants that have been transformed using recombinant DNA technology to enable them to synthesize selectively active antipathogenic substances, such as so-called "pathogenesis-associated proteins" (PRPs, see, for example, EP-A-0 392 225). Examples of such antipathogenic substances and transgenic plants capable of synthesizing such antipathogenic substances are known, for example, from EP-A-0 392 225, WO 95 / 33818, and EP-A-0353 191. Methods for producing such transgenic plants are generally known to those skilled in the art and are described, for example, in the disclosures mentioned above.

[0041] As used herein, the term "site" for useful plants is intended to include places where useful plants grow, where plant propagation material of useful plants is sown, or where plant propagation material of useful plants will be placed in the soil. An example of such a site is a field on which crop plants grow.

[0042] The term "plant propagation material" should be understood to refer to the reproductive parts of a plant, such as seeds, which can be used for plant propagation, as well as nutrient materials, such as cuttings or tubers (e.g., potatoes). References may include, for example, seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes, and parts of the plant. References may also include germinating plants and young plants that will be transplanted after germination or emergence. These young plants may be protected before transplanting by complete or partial treatment with maceration. Preferably, "plant propagation material" should be understood to refer to seeds.

[0043] These compositions of the present invention can also be used in the field of protecting stored goods from fungal attack. According to the invention, the term "stored goods" should be understood to refer to natural substances of plant and / or animal origin and their processed forms, derived from their natural life cycle and intended for long-term protection. Plant-derived stored goods (such as plants or parts thereof (e.g., stems, leaves, tubers, seeds, fruits, or grains)) can be protected in a freshly harvested state or in a processed form (e.g., pre-dried, moistened, crushed, ground, or baked). Also falling under the definition of stored goods is timber, whether in log form, such as building timber, transmission towers, and fences, or in the form of finished products, such as furniture or objects made from timber. Animal-derived stored goods are hides, leather, fur, hair, etc. The compositions according to the invention can prevent adverse effects such as decay, fading, or mold. Preferably, "stored goods" should be understood to refer to natural substances of plant origin and / or their processed forms, more preferably fruits and their processed forms (e.g., pome, stone fruit, berries, and citrus fruits and their processed forms). In another preferred embodiment of the invention, "stored goods" should be understood to mean timber.

[0044] Therefore, another aspect of the present invention is a method for protecting stored goods, the method comprising applying a composition according to the present invention to the stored goods.

[0045] The compositions of the present invention can also be used in the field of protecting technical materials from fungal attack. According to the present invention, the term "technical material" includes paper; blankets; buildings; cooling and heating systems; wall panels; ventilation and air conditioning systems, etc.; preferably, "technical material" should be understood to refer to wall panels. The compositions according to the present invention can prevent adverse effects such as decay, fading, or mold growth.

[0046] Furthermore, the compositions according to the invention are particularly effective against seed-borne and soil-borne diseases, such as those caused by *Alternaria* spp., *Ascochyta* spp., *Botrytis cinerea*, *Cercospora* spp., *Ervectomyces*, *Colletotrichum* spp., *Epicoccum* spp., *Fusarium graminearum*, *Fusarium moniliforme*, *Fusarium oxysporum*, *Fusarium proliferatum*, *Fusarium solani*, and *Fusarium glomeratum*. *graminis*, *Helminthosporium* spp., *Phoma* spp., *Pyrenophora graminea*, *Pyrenophora graminea*, *Rhizoctonia cerealis*, *Sclerotinia* spp., *Zymoseptoria* spp., *Ustilago*, *Tilletia* spp., *Typhula incarnata*, *Ustilago* spp., or *Verticillium* spp.; especially resistant to cereals such as wheat, barley, rye, or oats; corn; rice; cotton; soybeans; turf; sugar beets; rapeseed; potatoes; and legumes. Crops such as peas, lentils, or chickpeas; and pathogens of sunflowers.

[0047] Furthermore, the compositions according to the invention are particularly effective against postharvest diseases such as *Botrytis cinerea*, *Colletotrichum musae*, *Curvularia lunata*, *Fusarium semitecum*, *Geotrichum candida*, *Brachystomum rubrum*, *Streptococcus sclerotiorum*, *Streptococcus sclerotiorum*, *Mucor piriformis*, *Penicilium italicum*, *Penicilium solidum*, *Penicilium fingeriformis*, or *Penicilium expansum*; especially against pathogens of fruits such as pomegranates (e.g., apples and pears), stone fruits (e.g., peaches and plums), citrus fruits, melons, papayas, kiwifruit, mangoes, berries (e.g., strawberries), avocados, pomegranates, and bananas, as well as nuts.

[0048] The compositions according to the invention are particularly useful for controlling the following diseases in the following crops: Blumeria graminis in cereals; Uncinula necator in grapes; Sphaerotheca fuliginea in gourds; Puccinia species in cereals; and Phakopsora pachyrhizi in soybeans.

[0049] Generally, the weight ratio of component (A) to component (B) is in the range of 2000:1 to 1:1000. The weight ratio of component (A) to component (B) is preferably in the range of 100:1 to 1:100; more preferably in the range of 20:1 to 1:50; even more preferably in the range of 12:1 to 1:25; more preferably in the range of 10:1 to 1:10; even more preferably in the range of 5:1 to 1:15; and most preferably in the range of 2:1 to 1:5.

[0050] It has been discovered, unexpectedly, that certain weight ratios of component (A) to component (B) can produce synergistic activity. Therefore, another aspect of the invention is a composition in which components (A) and (B) are present in amounts that produce a synergistic effect. This synergistic activity is evident from the fact that the fungicidal activity of the composition comprising components (A) and (B) is greater than the sum of the fungicidal activities of components (A) and (B). This synergistic activity extends the scope of action of components (A) and (B) in two ways. First, by reducing the application ratio of components (A) and (B), yet maintaining the same level of effectiveness, meaning that even if the two individual components become completely ineffective at such low application ratios, the mixture of active ingredients still achieves a high degree of plant pathogen control. Second, by significantly broadening the spectrum of plant pathogens that can be controlled.

[0051] Not wanting to be bound by any particular theory, it is generally accepted that a synergistic effect exists as long as the combined effect of active ingredients is greater than the sum of the effects of individual components. For a given combination of active ingredients, the expected effect E follows the so-called Colby formula and can be calculated as follows (COLBY, SR, "Calculating synergistic and antagonistic responses of herbicide combination," Weeds, Vol. 15, pp. 20-22; 1967):

[0052] ppm = number of milligrams of active ingredient (=ai) per liter of spray mixture

[0053] X = % effect of active ingredient (based on active ingredient A) using p ppm.

[0054] Y = % effect of active ingredient (based on active ingredient B) using q ppm of active ingredient.

[0055] According to Colby, the expected effect of (additive) active ingredients A) + B) is expressed using the following formula:

[0056] The p+q ppm of the active ingredient is

[0057] If the observed effect (O) is greater than the expected effect (E), then the combined effect is superadditive, i.e., a synergistic effect exists. Mathematically, a synergistic effect corresponds to a positive value of the difference (OE). In the case of purely complementary addition of the active ingredient (expected activity), the difference (OE) is zero. A negative value of the difference (OE) indicates a loss of activity compared to the expected activity.

[0058] However, in addition to the actual synergistic effect relative to the fungicidal activity, the compositions according to the invention may also have other unexpectedly advantageous properties. Examples of such advantageous properties that may be mentioned are: more favorable degradability; improved toxicological and / or ecotoxicological behavior; or improved characteristics of useful plants, including: emergence, crop yield, more developed root system, increased tillering, increased plant height, larger leaves, less basal leaf mortality, stronger tillering, greener leaf color, less fertilizer required, less seed required, more tillering, earlier flowering, earlier grain maturity, less lodging, enhanced bud growth, improved plant vigor, and earlier germination.

[0059] Some compositions according to the present invention have systemic action and can be used as fungicides for leaf, soil and seed treatment.

[0060] Using the composition according to the invention, plant pathogenic microorganisms present on various useful plants or plant parts (fruits, flowers, leaves, stems, tubers, roots) can be inhibited or destroyed, while also protecting later-growing plant parts from attack by plant pathogenic microorganisms.

[0061] The compositions according to the invention can be applied to plant pathogens, useful plants threatened by microbial attack, their sites, their propagation materials, stored goods or technical materials.

[0062] The composition according to the invention can be applied before or after useful plants, their propagation materials, stored goods or technical materials are infected by microorganisms.

[0063] The amount of the composition according to the invention to be applied will depend on various factors, such as the compound used; the object to be treated, such as plants, soil or seeds; the type of treatment, such as spraying, dusting or seed dressing; the purpose of the treatment, such as prevention or treatment; the type of fungus to be controlled or the timing of application.

[0064] Typically, when component (A) is applied to a useful plant in combination with component (B), which is typically used at a ratio of 5 to 2000 g ai / ha, particularly 10 to 1000 g ai / ha, such as 100 g ai / ha, 250 g ai / ha, 500 g ai / ha, 800 g ai / ha, 1000 g ai / ha, or 1500 g ai / ha, component (A) is typically used at a ratio of 5 to 2000 g ai / ha, particularly 10 to 1000 g ai / ha, such as 50 g ai / ha, 75 g ai / ha, 100 g ai / ha, or 200 g ai / ha.

[0065] In agricultural practice, the application rate of the composition according to the invention depends on the type of desired effect and is typically in the range of 20 to 4000 g of total composition per hectare.

[0066] When the composition according to the invention is used to treat seeds, a ratio of 0.001 to 50 g of component (A) compound / kg seed, preferably from 0.01 to 10 g / kg seed, and 0.001 to 50 g of component (B) compound / kg seed, preferably from 0.01 to 10 g / kg seed, is generally sufficient.

[0067] The compositions of the present invention can be used in any conventional form, for example, in the form of double-packaged powders (DS) for dry seed treatment, emulsions (ES) for seed treatment, flowable concentrates (FS) for seed treatment, solutions (LS) for seed treatment, water-dispersible powders (WS) for seed treatment, capsule suspensions (CF) for seed treatment, gels (GF) for seed treatment, emulsion concentrates (EC), suspension concentrates (SC), suspension emulsions (SE), capsule suspensions (CS), water-dispersible granules (WG), emulsifiable granules (EG), water-in-oil emulsions (EO), oil-in-water emulsions (EW), microemulsions (ME), dispersible oil suspensions (OD), oil suspensions (OF), oil-soluble liquids (OL), soluble concentrates (SL), ultra-low volume suspensions (SU), ultra-low volume liquids (UL), technical grade (TK), dispersible concentrates (DC), wettable powders (WP), or any technically feasible formulation in combination with agriculturally acceptable adjuvants.

[0068] Such compositions can be produced in conventional ways, for example by mixing the active ingredient with at least one suitable inert formulation adjuvant (e.g., diluent, solvent, filler, and optionally other formulation components such as surfactants, biocides, antifreeze agents, adhesives, thickeners, and compounds that provide adjuvant effects). Conventional sustained-release formulations designed for long-term sustained efficacy can also be used. In particular, formulations intended for application in spray form, such as water-dispersible concentrates (e.g., EC, SC, DC, OD, SE, EW, EO, etc.), wettable powders, and granules, may contain surfactants such as wetting agents and dispersants, and other compounds that provide adjuvant effects, such as condensations of formaldehyde with naphthalene sulfonates, alkylaryl sulfonates, lignin sulfonates, fatty alkyl sulfates, and ethoxylated alkylphenols and ethoxylated fatty alcohols.

[0069] The compositions according to the invention may also contain additional pest control agents, such as fungicides, insecticides, or herbicides.

[0070] Using the composition and diluent according to the invention, the seed dressing is applied to seeds in a suitable seed dressing form, such as an aqueous suspension or dry powder having good adhesion to seeds, in a manner known per se. Such seed dressings are known in the art. The seed dressing may contain a single active ingredient or a combination of active ingredients in encapsulated form, for example, as sustained-release capsules or microcapsules.

[0071] Typically, formulations comprise from 0.01% to 90% by weight of an active agent, from 0% to 20% of an agriculturally acceptable surfactant, and from 10% to 99.99% of a solid or liquid formulation inert agent and one or more adjuvants, the active agent being composed of at least the compound of component (A) together with the compound of component (B), and optionally other active agents (particularly microbicides or preservatives, etc.). Concentrated forms of the composition typically contain between about 2% and 80% by weight, preferably between about 5% and 70% by weight of an active agent. Application forms of the formulation may, for example, contain from 0.01% to 20% by weight, preferably from 0.01% to 5% by weight of an active agent. However, commercially available products are preferably formulated as concentrates, and end users will typically use diluted formulations.

[0072] Therefore, another aspect of the present invention is a method for controlling rust on soybeans, the method comprising applying a composition comprising a compound having formula (I) to the plants, their sites or their propagation material.

[0073] The preferred method is that the plant pathogen is *Dioscorea beanus* rust fungus.

[0074] Another preferred method is the method of applying a composition comprising a compound having formula (I) to the plants or their sites, preferably to the plants.

[0075] A further preferred method is the method comprising applying a composition containing a compound having formula (I) to the propagation material of a plant.

[0076] The method according to the invention, particularly when a compound having formula (I) is used in combination with at least one compound (B) as described above, also allows for effective control of other harmful fungi frequently encountered in soybean plants. The most important rust disease in soybeans is caused by the rust fungus *Pseudomonas beanus*.

[0077] A preferred method is a method for controlling diseases on soybeans, particularly those caused by rust, comprising applying a composition containing a compound having formula (I) to these beneficial plants, their sites, or their propagation material.

[0078]

[0079] Where R 1 It is H, C(=O)CH3, or C(=O)CH2CH3. Additionally, mixtures of these compounds can be used advantageously.

[0080] Further characteristics of the composition comprising a compound having formula (I), the method of applying it to grains and the ratio of its application are as described for a composition comprising a compound having formula (I) and at least one other component (B) as described above.

[0081] Their application can be performed before and after the plants or parts thereof are infected by fungi. Preferably, treatment is performed before infection. When a compound having formula (I) is used on its own, the application ratio in the method according to the invention is as described above, typically from 5 to 2000 g ai / ha, particularly from 10 to 1000 g ai / ha, such as ratios of 50 g ai / ha, 75 g ai / ha, 100 g ai / ha, or 200 g ai / ha. During the growing season, the compound having formula (I) can be applied to these plants once or more. For use in the method according to the invention, the compound having formula (I) can be converted into conventional formulations described above, such as solutions, emulsions, suspensions, dusts, powders, pastes, and granules. The form of use will depend on the specific intended purpose; in each case, it should ensure a fine and uniform distribution of the compound having formula (I).

[0082] As used in this article, the term "plant" includes seedlings, shrubs, and crops of fruits and vegetables.

[0083] The following examples illustrate the present invention. "Active ingredient" refers to a mixture of component (A) and component (B) in a specific mixing ratio. The same formulation can be used in compositions containing only a compound having formula (I) as an active ingredient.

[0084] Examples of preparations

[0085]

[0086] The active ingredient is thoroughly mixed with other formulation components and the mixture is thoroughly ground in a suitable grinder to obtain a wettable powder, which can be diluted with water to provide a suspension of the desired concentration.

[0087]

[0088] The active ingredient is thoroughly mixed with other formulation components and the mixture is thoroughly ground in a suitable grinder to obtain a powder that can be used directly for seed treatment.

[0089] Emulsifiable concentrate

[0090]

[0091]

[0092] Emulsions with any required dilution that can be used in plant protection can be obtained by diluting such concentrates with water.

[0093]

[0094] Ready-to-use powders are obtained by mixing the active ingredient with a carrier and grinding the mixture in a suitable grinder. These powders can also be used for dry seed dressing.

[0095]

[0096] The active ingredient is mixed and ground with other formulation components, and the mixture is moistened with water. The mixture is then extruded and dried in an air stream.

[0097] suspension concentrate

[0098]

[0099] The finely ground active ingredient is thoroughly mixed with other formulation components to obtain a suspension concentrate, which can be diluted in water at any desired ratio. Using such a dilution, living plants, along with their propagation material, can be treated and protected against microbial contamination by spraying, pouring, or immersion.

[0100] Flowable concentrate for seed treatment

[0101]

[0102] The finely ground active ingredient is thoroughly mixed with other formulation components to obtain a suspension concentrate, which can be further diluted in water for application to seeds. Using such a dilution, propagation material can be treated and protected from microbial contamination by spraying, watering, or soaking.

[0103] Biological examples

[0104] Botrytis cinerea (gray mold):

[0105] Frozen fungal conidia were directly mixed into nutrient broth (PDB potato dextrose broth). A DMSO solution of the test compound was placed in a microtiter plate (96-well size), and nutrient broth containing fungal conidia was added. These test plates were incubated at 24°C, and the inhibition of growth was determined photometrically after 72 hours.

[0106]

[0107]

[0108] Multi-headed Corynebacterium (target leaf spot):

[0109] Frozen fungal conidia were directly mixed into nutrient broth (PDB potato dextrose broth). A DMSO solution of the test compound was placed in a microtiter plate (96-well size), and nutrient broth containing fungal conidia was added. These test plates were incubated at 24°C, and the inhibition of growth was determined spectrophotometrically at 620 nm after 3–4 days.

[0110]

[0111] Glomerellalagenariumsyn. Anthracnose fungus affecting cucurbits. (Colletotrichumlagenarium) (Anthrax):

[0112] Frozen fungal conidia were directly mixed into nutrient broth (PDB potato dextrose broth). A DMSO solution of the test compound was placed in a microtiter plate (96-well size), and nutrient broth containing fungal conidia was added. These test plates were incubated at 24°C, and the inhibition of growth was determined spectrophotometrically at 620 nm after 72 hours.

[0113]

[0114]

[0115]

[0116]

[0117] Phakopsorapachyrhizi (soybean rust fungus):

[0118] Four weeks after planting, whole soybean plants were treated with the described active ingredient. One day after spraying, leaf discs were cut from the first leaf with three leaves. Five replicates were performed at each ratio. One day after treatment, the leaf discs were inoculated with *Soybean rust* (Asian soybean rust). The leaf discs were evaluated 11 to 14 days after inoculation, and the activity was derived from the infection test between the treated and untreated plants. The ratios of active ingredients used are given in the table as g active ingredient (ai) / ha.

[0119]

[0120]

[0121]

[0122]

[0123]

[0124]

[0125]

[0126] Sclerotinia sclerotiorum (white sclerotium disease):

[0127] Mycelial fragments of fungi prepared from fresh liquid cultures were directly mixed into nutrient broth (PDB potato dextrose broth). A DMSO solution of the test compound was placed in a microtiter plate (96-well size), and nutrient broth containing fungal spores was added. These test plates were incubated at 24°C, and the inhibition of growth was determined spectrophotometrically at 620 nm after 72 hours.

[0128]

[0129] Soybean spores (brown spot disease):

[0130] Frozen fungal conidia were directly mixed into nutrient broth (PDB potato dextrose broth). A DMSO solution of the test compound was placed in a microtiter plate (96-well size), and nutrient broth containing fungal conidia was added. These test plates were incubated at 24°C, and growth inhibition was visually assessed after 72 hours.

[0131]

[0132]

[0133] Septoria tritici (leaf blisters):

[0134] Frozen fungal conidia were directly mixed into nutrient broth (PDB potato dextrose broth). A DMSO solution of the test compound was placed in a microtiter plate (96-well size), and nutrient broth containing fungal conidia was added. These test plates were incubated at 24°C, and the inhibition of growth was determined photometrically after 72 hours.

[0135]

[0136]

[0137]

[0138]

Claims

1. A composition suitable for controlling diseases caused by plant pathogens, comprising: (A) Compounds having Formula I: Where R 1 It is C(=O)CH2CH3, or an agronomically acceptable salt thereof; and (B) At least one compound selected from the group consisting of: 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thio-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methylformamidinium, N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl] [-phenyl]-N-ethyl-N-methylformamidinium, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiobenzamide, 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide and N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, or combinations thereof; When component (B) is N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiobenzamide, 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide, or N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, the weight ratio of component (A) to component (B) is in the range of 2:1 to 1:1000. When component (B) is 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thio-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, the weight ratio of component (A) to component (B) is in the range of 0.06:0.5 to 1:

200. When component (B) is N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidin, the weight ratio of component (A) to component (B) is in the range of 1:5 to 0.03:0.

625. When component (B) is N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidinium, the weight ratio of component (A) to component (B) is in the range of 1:2.5 to 1:

10.

2. A fungicidal composition comprising a fungicide-effective amount of the composition according to claim 1, and a suitable carrier or diluent thereof, and optionally comprising additional pest control agents.

3. A formulation comprising the fungicidal composition according to claim 2, comprising from 0.01% to 90% by weight of an active agent, from 0% to 20% by weight of an agriculturally acceptable surfactant, and from 10% to 99.99% by weight of a solid or liquid formulation inert agent and one or more adjuvants, wherein the active agent comprises at least the compound of component (A) together with the compound of component (B), and optionally other active agents.

4. A concentrated composition for dilution by a user, comprising the composition of claim 1, the antifungal composition of claim 2, or the formulation of claim 3, wherein the active agent is contained in amounts from 2% to 80% by weight.

5. A seed dressing preparation comprising the composition according to claim 1, further comprising a diluent.

6. The seed dressing preparation according to claim 5 is in the form of a capsule, as a sustained-release capsule or microcapsule.

7. A method for combating and controlling plant pathogens, comprising applying an effective amount of the composition according to claim 1 or the fungicide composition according to claim 2 to a pest, a site of a pest, or a plant susceptible to pest invasion, other than methods of treating a human or animal body by surgery or therapy and diagnostic methods performed on a human or animal body.

8. The method of claim 7 for controlling rust on soybeans or grains, comprising applying to the plant, its site or its propagation material the composition of claim 1, the fungicidal composition of claim 2, the formulation of claim 3, the concentrated composition of claim 4, or the seed dressing formulation of claim 5 or 6.

9. The method according to any one of claims 7 to 8, wherein, The plant pathogen is *Dioscorea beanus* rust fungus.

10. The method according to any one of claims 7 to 8, wherein, The composition further comprises a diluent.

11. Use of the composition according to claim 1 or the fungicidal composition according to claim 2, wherein the use is for combating and controlling plant pathogens.

12. Use of the formulation according to claim 3, wherein the use is for combating and controlling plant pathogens.

13. Use of the concentrated composition according to claim 4, wherein the use is for combating and controlling plant pathogens.

14. Use of the seed dressing preparation according to claim 5 or 6, wherein the use is for combating and controlling plant pathogens.

15. The use according to any one of claims 11-14, wherein the use is for combating and controlling rust fungi in soybean plants.

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