Antifungal compositions containing agaricone derivatives

Abstract

This invention relates to fungicidal compositions comprising at least one compound selected from the group consisting of: (I-1) (Z)-2-(5-cyclobutyl-2-methylphenoxy)-3-methoxy-propane-2-enoate, (I-2) (Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxy-propane-2-enoate, (I-3) (Z)-2-(5-cyclopropyl-2-methylphenoxy)-3-methoxy-propane-2-enoate, (I-4) (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxy-propane-2-enoate; and at least one active mixture II. The invention also relates to an agrochemical composition comprising the composition and a solvent of a solid carrier. Furthermore, this invention relates to the non-therapeutic use of the compositions of the invention for controlling pathogenic harmful fungi of plants.

Description

[0001] This invention relates to an antifungal composition comprising, as active component 1), at least one compound selected from the group consisting of:

[0002] (I-1) (Z)-2-(5-cyclobutyl-2-methylphenoxy)-3-methoxy-prop-2-enoic acid methyl ester

[0003] (I-2) (Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxy-prop-2-enoic acid methyl ester

[0004] (I-3) (Z)-2-(5-cyclopropyl-2-methylphenoxy)-3-methoxy-prop-2-enoic acid methyl ester

[0005] (I-4) (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxy-prop-2-enoic acid methyl ester

[0006] As active component 2), at least one compound selected from the group consisting of, or its N-oxide, or an agriculturally useful salt.

[0007] (II-1) Flusulfanilamide

[0008] (II-2) Fluopyram

[0009] (II-3) Fluopyridazine

[0010] (II-4) Trifluoropyridine

[0011] (II-5) Methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propionate

[0012] (II-6) 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propionic acid

[0013] (II-7) 1-[[4-[5-[chloro(difluoro)methyl]-1,2,4-oxadiazol-3-yl]-2-fluoro-phenyl]methyl]pyrazole-4-carboxylic acid ethyl ester

[0014] (II-8) 1-[[5-[5-[chloro(difluoro)methyl]-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylic acid ethyl ester

[0015] (II-9) 5-[chloro(difluoro)methyl]-3-[4-[(3-ethynylpyrazol-1-yl)methyl]phenyl]-1,2,4-oxadiazole

[0016] (II-10) 1-[[4-[5-[chloro(difluoro)methyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]-1,3-dimethoxy-urea

[0017] (II-11) N-[[4-[5-[chloro(difluoro)methyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]-N,2-dimethoxy-propionamide

[0018] (II-12) 2-(4-fluorophenoxy)-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl ketone

[0019] (II-13) 2-[(6-fluoro-3-pyridyl)oxy]-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetone

[0020] (II-14) 2-(4-fluoroanilino)-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ketene

[0021] (II-15) N-[1-[[3-[2-(5-fluoro-2-methoxy-phenyl)-2-hydroxy-ethyl]-5-[(Z)-N-isopropoxy-C-methyl-carboimino]-2,6-dioxo-pyrimidin-1-yl]methyl]-2-methyl-propyl]-2-methyl-propionamide

[0022] (II-16) N-[1-[[3-[2-(5-fluoro-2-methoxy-phenyl)-2-hydroxy-ethyl]-5-[(Z)-N-isopropoxy-C-methyl-carboimino]-2,6-dioxo-pyrimidin-1-yl]methyl]-2-methyl-propyl]-2,2-dimethyl-propionamide

[0023] (II-17) N-[2-[3-[2-(5-fluoro-2-methoxy-phenyl)-2-hydroxy-ethyl]-5-[(Z)-N-isopropoxy-C-methyl-carboimino]-2,6-dioxo-pyrimidin-1-yl]-1-methyl-ethyl]-2-methyl-propionamide

[0024] (II-18) N-[2-[3-[2-hydroxy-2-(2-methoxyphenyl)ethyl]-5-[(Z)-N-isopropoxy-C-methyl-carboimino]-2,6-dioxo-pyrimidin-1-yl]-1-methyl-ethyl]-2-methyl-propionamide

[0025] (II-19) N-[2-[3-[2-(2-cyanoethoxy)-2-(5-fluoro-2-methoxy-propyl)ethyl]-5-[(Z)-N-isopropoxy-C-methyl-carboimino]-2,6-dioxo-pyrimidin-1-yl]-1-methyl-ethyl]-2-methyl-propionamide

[0026] (II-20) 3-[3-(3-chloro-2-fluoro-phenoxy)-6-methyl-pyridazin-4-yl]-5-[(2-chloro-4-methyl-phenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine

[0027] (II-21) (5S)-3-[3-(3-chloro-2-fluoro-phenoxy)-6-methyl-pyridazin-4-yl]-5-[(2-chloro-4-methyl-phenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine

[0028] (II-22) (5R)-3-[3-(3-chloro-2-fluoro-phenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methyl-phenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine

[0029] (II-23) 1-[4-[4-[5-(2,6-dichlorophenyl)-4,5-dihydroisoxazo-3-yl]thiazo-2-yl]-1-piperidinyl]-2-[3-(trifluoromethyl)pyrazin-2-yl]oxy-acetone

[0030] (II-24) 1-[4-[4-[5-(2-chloro-6-fluoro-phenyl)-4,5-dihydroisoxazo-3-yl]thiazo-2-yl]-1-piperidinyl]-2-[[3-(trifluoromethyl)-2-pyridinyl]oxy]ethenone

[0031] (II-25) 4-[4-[5-(2-bromo-6-fluoro-phenyl)-4,5-dihydroisoxazol-3-yl]thiazolyl-2-yl]piperidine-1-carboxylic acid tert-butyl ester

[0032] (II-26) ((2-(3-(2-(1-(2-(3,5-bis(trifluoromethyl)-1H-pyrazole-1-yl)acetyl)piperidin-4-yl)thiazo-4-yl)-4,5-dihydroisoxazol-5-yl)-3-fluorophenyl)imino)dimethyl-λ6-sulfonone)

[0033] (II-27) ((2-(3-(2-(1-(2-(3,5-bis(difluoromethyl)-1H-pyrazol-1-yl)acetyl)piperidin-4-yl)thiazo-4-yl)-4,5-dihydroisoxazol-5-yl)-3-fluorophenyl)imino)dimethyl-λ6-sulfonone)

[0034] (II-28) ((2-(3-(2-(1-(2-(3,5-bis(difluoromethyl)-1H-pyrazol-1-yl)acetyl)piperidin-4-yl)thiazo-4-yl)-4,5-dihydroisoxazol-5-yl)-3-chlorophenyl)imino)(isopropyl)(methyl)-λ6-sulfonone

[0035] (II-29) ((2-(3-(2-(1-(2-(3,5-bis(trifluoromethyl)-1H-pyrazole-1-yl)acetyl)piperidin-4-yl)thiazo-4-yl)-4,5-dihydroisoxazol-5-yl)-3-fluorophenyl)imino)(isopropyl)(methyl)-λ6-sulfonone

[0036] (II-30) ((2-(3-(2-(1-(2-(3,5-bis(difluoromethyl)-1H-pyrazol-1-yl)acetyl)piperidin-4-yl)thiazo-4-yl)-4,5-dihydroisoxazol-5-yl)-3-(trifluoromethyl)phenyl)imino)dimethyl-λ6-sulfonone

[0037] (II-31) ((3-fluoro-2-(3-(2-(1-(2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetyl)piperidin-4-yl)thiazo-4-yl)-4,5-dihydroisoxazol-5-yl)phenyl)imino)dimethyl-λ6-sulfonone)

[0038] (II-32) N-(1-benzyl-1,3-dimethylbutyl)-8-fluoroquinoline-3-carboxamide

[0039] (II-33) N-[(1R)-1-benzyl-1,3-dimethylbutyl]-8-fluoroquinoline-3-carboxamide

[0040] (II-34) N-[(1S)-1-benzyl-1,3-dimethylbutyl]-8-fluoroquinoline-3-carboxamide

[0041] The weight ratio of compound I to compound II is 10:1 to 1:10.

[0042] This invention also relates to an agricultural chemical composition comprising a solvent of the composition and a solid carrier. Furthermore, this invention relates to the non-therapeutic use of the compositions of this invention for controlling pathogenic fungi of plants.

[0043] The compounds I-1 to I-4 defined above for component 1) are collectively referred to herein as "compounds having formula I" or "compound I". The compounds II-1 to II-34 defined above for component 2) are collectively referred to herein as "compounds having formula II" or "compound II".

[0044] Compounds I-1 to I-4 and mixtures thereof are known from WO 2021 / 176057. Additionally, they are known from WO 2020213739, WO 2021230382, EP 4295688, WO 2022 / 249074, WO 2022 / 230804, WO 2023213626, WO 2023213670, WO 2021 / 255070, EP 4295688, WO 2022130188, WO 2022243810, WO 2023 / 111215 and http: / / www.bcpcpesticidecompendium.org / Compounds II-1 to II-34 are known in the study.

[0045] A typical problem in the field of pest control is the need to reduce the dosage rate of active ingredients to minimize or avoid adverse environmental or toxicological effects while still allowing for effective pest control. In this invention, the term "pest" includes harmful fungi and animal pests.

[0046] Another issue encountered involves the need for available pest control agents that can effectively resist broad-spectrum harmful fungi and harmful animal pests.

[0047] There is also a need for pest control agents that combine knockdown activity with long-term control (i.e., rapid action and sustained action).

[0048] Another difficulty associated with the use of pest control agents is that, in many cases, repeated and specific application of a single pest control compound leads to the rapid selection of pests (meaning animal pests and harmful fungi) that have developed natural or adaptive resistance to the active compound in question. Therefore, pest control agents that help prevent or overcome resistance are needed.

[0049] Controlling fungal diseases in soybeans, in particular, is a challenge, and now more than one active ingredient is needed to achieve sufficient activity. It is anticipated that all future products will consist of at least two active ingredients (binary compositions).

[0050] Therefore, the object of the present invention is to provide a composition that, from the perspective of effective resistance management and effective control of plant pathogenic harmful fungi, has improved antifungal activity (synergistic composition) and a broadened activity spectrum at the lowest possible application rate and with a reduced total amount of applied active compound.

[0051] Therefore, we have found that this objective is achieved by compositions as defined herein, which comprise compound I and at least one compound II.

[0052] In particular, it has been found that compositions as defined at the beginning exhibit significantly enhanced effects in pest control compared to control rates that could be achieved using individual compounds, and / or are suitable for improving plant health when applied to plants, plant parts, seeds or their growing sites.

[0053] Furthermore, we have found that simultaneous (i.e., combined or separate) application of Compound I and Compound II, or sequential application of Compound I and Compound II, allows for better control of harmful fungi compared to the control that may be achieved using only the individual compounds (synergistic composition). Therefore, in the context of this invention, the term "composition" should mean the physical composition of the components prior to application, or the result of simultaneous (i.e., combined or separate) application of Compound I and Compound II to fungi, their habitat or seeds, soil, or plants to be protected from fungal invasion.

[0054] Compound I and / or compound II can exist in different crystal forms (which may differ in biological activity).

[0055] The scope of this invention includes compositions of (R)- and (S)-isomers of compounds I and / or II having one or more chiral centers, as well as racemic mixtures. Due to the hindered rotation of asymmetric substituents, trans-restricted isomers of active compounds I and / or II may exist. They also form part of the subject matter of this invention.

[0056] Agriculturally acceptable salts of active compounds I and II particularly include salts of cations or acid addition salts of acids, where the cations and anions do not adversely affect the fungicidal activity of these active compounds. Therefore, suitable cations include, in particular, alkali metal (preferably sodium and potassium) ions, alkaline earth metal (preferably calcium, magnesium, and barium) ions, transition metal (preferably manganese, copper, zinc, and iron) ions, and also ammonium ions, which, if desired, may have one to four C1-C4-alkyl substituents and / or one phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, as well as phosphonium ions, sulfonium ions, preferably tri(C1-C4-alkyl)sulfonium, and sulfonium oxide ions, preferably tri(C1-C4-alkyl)sulfonium oxide. The available anions for acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and anions of C1-C4-alkyl acids, preferably formate, acetate, propionate, and butyrate. They can be formed by reacting compound I with an acid corresponding to the anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, or nitric acid.

[0057] In binary mixtures, the weight ratio of component 1) to component 2) generally depends on the properties of the components used, typically in the range of 1:10,000 to 10,000:1, often in the range of 1:100 to 100:1, frequently in the range of 1:50 to 50:1, preferably in the range of 1:20 to 20:1, more preferably in the range of 1:10 to 10:1, even more preferably in the range of 1:4 to 4:1, and particularly in the range of 1:2 to 2:1. According to another embodiment, the weight ratio of component 1) to component 2) is generally from 1000:1 to 1:1, often from 100:1 to 1:1, frequently from 50:1 to 1:1, preferably from 20:1 to 1:1, more preferably from 10:1 to 1:1, even more preferably from 4:1 to 1:1, and particularly in the range of 2:1 to 1:1. According to another embodiment, the weight ratio of component 1) to component 2) is typically from 20,000:1 to 1:10, often from 10,000:1 to 1:1, frequently from 5,000:1 to 5:1, preferably from 5,000:1 to 10:1, more preferably from 2,000:1 to 30:1, even more preferably from 2,000:1 to 100:1, and particularly in the range of 1,000:1 to 100:1. According to another embodiment, the weight ratio of component 1) to component 2) is typically from 1:1 to 1:1000, often from 1:1 to 1:100, frequently from 1:1 to 1:50, preferably from 1:1 to 1:20, more preferably from 1:1 to 1:10, even more preferably from 1:1 to 1:4, and particularly in the range of 1:1 to 1:2.

[0058] According to another embodiment, the weight ratio of component 1) to component 2) is typically from 10:1 to 1:20,000, often from 1:1 to 1:10,000, frequently from 1:5 to 1:5,000, preferably from 1:10 to 1:5,000, more preferably from 1:30 to 1:2,000, even more preferably from 1:100 to 1:2,000, and particularly in the range of 1:100 to 1:1,000.

[0059] According to another embodiment, compound I and compound II are typically present in a ratio of 20:1 to 1:20, often 15:1 to 1:15, more often 10:1 to 1:10, even more often 9:1 to 1:9, often 8:1 to 1:8, preferably 7:1 to 1:7, more preferably 6:1 to 1:6, even more preferably 5:1 to 1:5, most preferably 4:1 to 1:4, particularly preferably 3:1 to 1:3, especially 2:1 to 1:2, specifically 1:1.

[0060] Compound I and Compound II may also be present in a ratio of 20:1 to 1:1, often 15:1 to 1:1, more often 10:1 to 1:1, even more often 9:1 to 1:1, often 8:1 to 1:1, preferably 7:1 to 1:1, more preferably 6:1 to 1:1, even more preferably 5:1 to 1:1, most preferably 4:1 to 1:1, especially preferably 3:1 to 1:1, and particularly preferably 2:1 to 1:1.

[0061] Compound I and compound II may further exist in a ratio of 1:1 to 1:20, often 1:1 to 1:15, more often 1:1 to 1:10, even more often 1:1 to 1:9, often 1:1 to 1:8, preferably 1:1 to 1:7, more preferably 1:1 to 1:6, even more preferably 1:1 to 1:5, most preferably 1:1 to 1:4, particularly preferably 1:1 to 1:3, especially 1:1 to 1:2.

[0062] In a preferred aspect, the present invention relates to antifungal compositions M.1 to M.680, each identified in a row of Table M below, wherein components 1) and 2) are identified together with their relative amounts (weight ratios).

[0063] Table M

[0064]

[0065] Some of the binary compositions and agrochemical compositions according to the invention are systemic and can be used as foliar fungicides, seed dressing fungicides, and soil fungicides for crop protection. Furthermore, they are suitable for controlling harmful fungi, particularly those found in wood or plant roots.

[0066] The binary compositions and their agrochemical compositions according to the present invention are particularly important for controlling a variety of plant pathogenic fungi on various cultivated plants, including: cereals such as wheat, rye, barley, triticale, oats, or rice; sugar beets such as sugar beets or forage beets; fruits such as pome, drupes, or berries such as apples, pears, plums, peaches, apricots, cherries, strawberries, raspberries, blackberries, or gooseberries; legumes such as lentils, peas, alfalfa, or soybeans; oilseed plants such as rapeseed, mustard, olives, sunflowers, coconuts, cocoa beans, castor oil plants, oil palms, peanuts, or soybeans; cucurbits such as pumpkins, cucumbers, or melons; and fiber plants such as cotton, flax, and hemp. Jute; citrus fruits such as oranges, lemons, grapefruits, or tangerines; vegetables such as spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, melons, or peppers; laurel plants such as avocados, cinnamon, or camphor; energy and raw material plants such as corn, soybeans, rapeseed, sugarcane, or oil palm; corn; tobacco; nuts; coffee; tea; bananas; grapevines (table grapes and grape juice vines); hops; turfgrass; stevia (also known as stevia); natural rubber plants or ornamental and forestry plants such as flowers, shrubs, broad-leaved trees, or evergreens such as conifers; and plant propagation materials such as seeds, and crop materials of these plants.

[0067] Preferably, the binary composition and its agrochemical composition according to the present invention are used to control a variety of fungi on field crops, such as wheat, such as common wheat (spring wheat, winter wheat and intermediate wheat), spring barley and winter barley (barley), spring triticale and winter triticale; corn (maize); legumes, such as lentils (small lentils, lentils), soybeans (cultivated soybeans, hairy soybeans) and common beans (peas), such as dried beans or field beans and fresh beans, including kidney beans, green beans, string beans, common beans (common beans (p. vulgaris), dwarf common beans); oil crops, such as spring rapeseed and winter rapeseed (European rapeseed), canola rapeseed (European rapeseed and turnip) or sunflower (sunflower (Helianthus annuus)); tomato (yellow cherries, also known as cherry tomatoes), potato (solanum tuberosum)).

[0068] According to a preferred embodiment of the present invention, compositions M.1 to M.680 are used to control plant pathogenic fungi on wheat such as common wheat (spring wheat, winter wheat and intermediate wheat).

[0069] According to a preferred embodiment of the present invention, compositions M.1 to M.680 are used to control plant pathogenic fungi on spring barley and winter barley (barley).

[0070] According to a preferred embodiment of the present invention, compositions M.1 to M.680 are used to control plant pathogenic fungi on spring and winter triticale.

[0071] According to a preferred embodiment of the present invention, compositions M.1 to M.680 are used to control plant pathogenic fungi on maize (corn).

[0072] According to a preferred embodiment of the present invention, compositions M.1 to M.680 are used to control plant pathogenic fungi on legumes.

[0073] According to a preferred embodiment of the present invention, compositions M.1 to M.680 are used to control plant pathogenic fungi on the following plants: lentils (small beans, lentils).

[0074] Soybeans (cultivated soybeans, pubescent soybeans) and common beans (peas), such as dried beans or field beans and fresh beans, including kidney beans, green beans, string beans, common beans (peas, dwarf beans); oilseed plants, such as spring rapeseed and winter rapeseed (European rapeseed), canola rapeseed (European rapeseed and turnip), or sunflowers; tomatoes (yellow cherries, also known as cherry tomatoes), potatoes.

[0075] According to a preferred embodiment of the present invention, compositions M.1 to M.680 are used to control plant pathogenic harmful fungi on soybeans (cultivated soybeans, hairy soybeans).

[0076] According to a preferred embodiment of the present invention, compositions M.1 to M.680 are used to control plant pathogenic harmful fungi on beans (peas), such as dried beans or field beans and fresh beans, including kidney beans, green beans, string beans, common beans (peas, dwarf beans).

[0077] According to a preferred embodiment of the present invention, compositions M.1 to M.680 are used to control plant pathogenic fungi on oilseed plants.

[0078] According to a preferred embodiment of the present invention, compositions M.1 to M.680 are used to control plant pathogenic fungi on spring rapeseed and winter rapeseed (European rapeseed).

[0079] According to a preferred embodiment of the present invention, compositions M.1 to M.680 are used to control plant pathogenic fungi on canola (European rape and turnip).

[0080] According to a preferred embodiment of the present invention, compositions M.1 to M.680 are used to control plant pathogenic fungi on sunflowers.

[0081] According to a preferred embodiment of the present invention, compositions M.1 to M.680 are used to control plant pathogenic fungi on sunflowers.

[0082] According to a preferred embodiment of the present invention, compositions M.1 to M.680 are used to control plant pathogenic fungi on tomatoes (also known as cherry tomatoes).

[0083] According to a preferred embodiment of the present invention, compositions M.1 to M.680 are used to control plant pathogenic harmful fungi on potatoes.

[0084] Preferably, the binary composition and its agrochemical composition according to the present invention are used to control the following pathogenic factors of plant diseases:

[0085] White rust (white rust) is caused by species of the genus *Albugo* on ornamental plants, vegetables (e.g., *Albugo tragopogonis*), and sunflowers (e.g., *Albugo tragopogonis*). It also affects vegetables (e.g., *Albugo dauci* or *Albugo porri*), rapeseed (*Albugo brassicicola* or *Albugo brassicae*), sugar beets (*Albugo tenuis*), fruits (e.g., *Albugo grandis*), rice, soybeans, potatoes, and tomatoes (e.g., *Albugo solani*, *Albugo cylindrica*, or *Albugo alternata*), tomatoes (e.g., *Albugo solani* or *Albugo alternata*), and wheat (e.g., *Albugo leucocephala*). Alternaria species on *Alternaria triticina* (Alternaria leaf spot); Aphanomyces species on sugar beets and vegetables; Ascochyta species on cereals and vegetables, such as *A. tritici* (anthracnose) on wheat and *A. hordei* (barley); *Aureobasidium zeae* (synonym *Kapatiella zeae*) on maize; Bipolaris and Drechslera species (sexual form: *Cochliobolus* species), such as *D. maydis* (small leaf spot) or *B. zeicola* (large leaf spot) on maize, such as *B. zeicola* (root rot) on cereals. Sorokiniana) and, for example, B. oryzae on rice and turfgrass; Blumeriagraminis (formerly known as Erysiphe graminis) (powdery mildew) on cereals (e.g., wheat or barley); Botrytis cinerea (sexual form: Botryotinia fuckeliana: gray mold) on fruits and berries (e.g., strawberries), vegetables (e.g., lettuce, carrots, celery, and cabbage); Botrytis squamosa or Botrytis squamosa on onion family plants, rapeseed, ornamental plants (e.g., Botrytis eliptica), vines, forest plants, and wheat.* *allii*; *Bremia lactucae* on lettuce (downy mildew); *Ceratocystis* species (synonym *Ophiostoma*) on broadleaf and evergreen trees (rot or wilting), such as *C. ulmi* on elm trees (Dutch elm disease); maize (e.g., gray leaf spot: *C. zeae-maydis*), rice, sugar beets (e.g., *C. beticola*), sugarcane, vegetables, coffee, soybeans (e.g., *C. sojina* or *C. kikuchii*) and *Cercospora* species on rice (Cercospora leaf spot); *Cladobotryum* species (synonym *Dactylium*) on mushrooms (e.g., *C. philodendron*). Mycophilum (formerly known as Dactylium dendroides, sexual forms: Nectria albertinii, Nectria rosella, synonym Hypomyces rosellus); Cladosporium species on tomatoes (e.g. C. fulvum: leaf mold) and cereals, such as C. herbarum on wheat (smut); Claviceps purpurea on cereals (ergot); C. carbonum on maize, C. sativus on cereals, asexual form: B. sorokinina) and C. miyabeanus on rice, asexual form: H. Species of the genus *Helminthosporium* (asexual form: *Bipolaris*) on *oryzae* (leaf spot); cotton (e.g., *C. gossypii*), maize (e.g., *C. graminicola*, anthracnose stem rot), berries, potatoes (e.g., *C. coccodes*, black spot), beans (e.g., *C. lindemuthianum*), soybeans (e.g., *C. truncatum* or *C. gloeosporioides*), vegetables (e.g., *C. lagenarium* or *C. capsici*), fruits (e.g., *C. acutatum*), coffee (e.g., *C. coffee*).Colletotrichum species (sexual form: Glomerella) on coffee berry anthracnose (C. kahawae) and Colletotrichum discoidus on various crops; Corticium species, such as C. sasakii on rice (sheath blight); Coryne-spora cassiicola on soybeans, cotton, and ornamental plants (leaf spot); Cycloconium species, such as C. oleaginum on olive trees; and Neonectrialiriodendri on fruit trees and vines (e.g., C. liriodendri, sexual form: Neonectrialiriodendri): Black Foot disease. Diseases) and Cylindrocarpon species on ornamental plants (e.g., fruit tree canker or vine decay, sexual type: Nectria or Neonectria species); Dematophora necatrix on soybeans (sexual type: Rosellia necatrix) (root and stem rot); Diaporthe species, such as D. phaseolorum on soybeans (damping-off); maize, cereals such as barley (e.g., barley net blotch necatrix, net blotch) and wheat (e.g., wheat dermatophyte). tritici-repentis: brown spot disease), *Drechslera* species (synonym: *Helminthosporium*, sexual form: *Pyrenophora*) on rice and turfgrass; Esca disease (apical dieback, apoplexy) on vines, caused by *Formitiporia punctata* (synonym: *Phellinus punctata*), *F. mediterranea*, *Phaeomoniella chlamydospora* (formerly *Phaeoacremonium chlamydosporum*), *Phaeoacremonium aleophilum*, and / or *Botryosphaeria obtusa*; pome (*E. pyri*), berries (*E. pyri*).Veneta: Anthracnose) and Elsinoe species on vines (E. ampelina: Anthracnose); Entyloma oryzae on rice (leaf smut); Epicoccum species on wheat (black mold); Erysiphe species on sugar beets (E. betae) and vegetables (e. pisi) such as cucurbits (e. cichoracearum) and cabbage and rapeseed (e. cruciferarceus E. cruciferarum) (powdery mildew); Eutypa lata (grape ulcer or shoot dieback) on fruit trees, vines and ornamental trees; asexual form: Cytosporina *Lata*, a synonym of *Libertellablepharis*; *Exserohilum* species (synonym of *Exserohilum*) on maize (e.g., *E. turcicum*); *Fusarium* species (sexual form: *Gibberella*) on various plants (wilt, root or stem rot), such as *F. graminearum* or *F. culmorum* on cereals (e.g., wheat or barley) (root rot, scab, or wilt), *F. oxysporum* on tomatoes, *F. solani* (soybean-specific, now synonymous with *F. virguliforme*) and *F. tucumaniae* (South American soybean sudden death syndrome pathogen) on soybeans, and *F. brasiliensis*. *Fusarium brasiliense*, and *F. verticillioides* on maize; *Gaeumannomyces graminis* (take-all) on cereals (e.g., wheat or barley) and maize; *G. zeae* species on cereals (e.g., *G. fujikuroi*: Bakanae disease) and rice (e.g., *G. fujikuroi*); *Glomerella cingulata* on vines, pome fruits and other plants, and *G. cotyledonum* on cotton.gossypii; grain-staining complex on rice; *Guignardia bidwellii* (black rot) on vines; *Gymnosporangium* species on Rosaceae and juniper, such as *G. sabinae* (rust) on pears; *Helminthosporium* species (synonym: *Drechslera*, sexual form: *Cochliobolus*) on corn, cereals, potatoes, and rice; *Hemileia* species, such as *H. vastatrix* (coffee leaf rust) on coffee; *Isariopsis clavispora* (synonym: *Cladosporium vitis*) on vines; *Macrophomina phaseolina* (synonym: *Macrophomina*) on soybeans and cotton. Phaseoli (root and stem rot); Microdochium (synonym Fusarium) (powdery mildew) on cereals (e.g., wheat or barley); Microsphaera diffusa (powdery mildew) on soybeans; Monilinia species on drupes and other Rosaceae plants, such as *M. laxa*, *M. fructicola*, and *M. fructigena* (synonym *Monilia* species, flower rot and branch blight, brown rot); Mycosphaerella species on cereals, bananas, berries, and peanuts, such as *M. graminicola* on wheat (asexual form: *Zymoseptoriatritici*, formerly known as *Septoria*). tritici: leaf spot disease) or Fiji coccidia (M. fijiensis) on bananas (synonym Pseudocercospora fijiensis: black leaf spot) and banana yellow stripe leaf spot fungus (M. musicola), peanut coccidia (M. arachidicola) (synonym peanut coccidia (M. arachidis) or peanut cercospora arachidis) and Berkeley coccidia (M. berkeleyi) on peas.*P. brassiciola* on rapeseed (e.g., *P. brassicae*), rapeseed (e.g., *P. parasitica*), onion (e.g., *P. destructor*), tobacco (*P. tabacina*), and soybean (e.g., *P. manshurica*) species of *Peronospora* (downy mildew); *P. meibomiae* and *P. meibomiae* rust on soybean (soybean rust); *Phialophora* species, such as on vines (e.g., *P. tracheiphila* and *P. tetraspora*) and soybean (e.g., *P. gregata*: stem rot); *Phoma* on rapeseed and cabbage. *Phomopsis* species on sunflowers, vines (synonyms: *Leptosphaeria biglobosa* and *L. maculans*: root and stem rot), and sugar beet (*P. betae*) (root rot, leaf spot, and damping-off), and maize (*P. zeae-maydis*) (synonym: *Phyllostica zeae*); *Phomopsis* species on sunflowers, vines (e.g., grape *P. viticola*: can and leaf spot) and soybeans (e.g., stem rot: *P. phaseoli*, sexual form: *Diaporthe phaseolorum*); *Physoderma* on maize. Maydis (brown spot disease); Phytophthora species (wilt, roots, leaves, fruits, and stems) on various plants, such as red peppers and melons (e.g., *Phytophthora capsici*), soybeans (e.g., *Phytophthora megasperma*, synonym *Phytophthora sojae*), potatoes and tomatoes (e.g., *Phytophthora infestans*: late blight) and broadleaf trees (e.g., *Phytophthora ramorum*: sudden death of oak); *Plasmodiophora brassicae* (club root) on cabbage, rapeseed, radish, and other plants; *Plasmopara* species, such as *P. viticola* (grape downy mildew) on vines and *P. hols* (sunflower) on sunflowers.halstedii); species of *Podosphaera* (powdery mildew) on Rosaceae plants, hops, pome fruits and berries, such as *P. leucotricha* on apples and *P. xanthii* on melons; species of *Polymyxa* on cereals such as barley and wheat (*P. graminis*) and sugar beets (*P. betae*), and viral diseases transmitted by these; *Pseudocercosporella herpotrichoides* (synonym *Oculimacula yallundae*), *O. acuformis*: eye spot disease, sexual form: *Tapesia*. *Pseudoperonospora* species (downy mildew) on various plants, such as *P. cubensis* on gourds or *P. humili* on hops; *Pseudopeziculatracheiphila* (red fire disease or rotbrenner, asexual form: *P.*) on vines; *Puccinia* species (rust) on various plants, such as *P. triticina* (brown rust or leaf rust), *P. striiformis* (stripe rust or yellow rust), *P. hordei* (dwarf rust), *P. graminis* (stem rust or black rust), or *P. crypticus* (…) on cereals (e.g., wheat, barley, or rye). *Recondita* (brown rust or leaf rust), *P. kuehnii* (citrus rust) on sugarcane and *P. asparagi* (Asparagus rust) on asparagus; species of *Pyrenopeziza*, such as *P. brassicae* on rapeseed; *Pyrenophora tritici-repentis* (asexual form: *Drechslera tritici-repentis*) (brown spot) on wheat or *P. teres* (net blotch) on barley; species of *Pyricularia* on rice, such as *P. oryzae* (sexual form: *Magnaporthe grisea*): rice blast, and *P. griseus* on turfgrass and cereals.*Pythium* species (damping-off) on grasses, rice, corn, wheat, cotton, rapeseed, sunflower, soybean, sugar beet, vegetables, and many other plants (e.g., *P. ultimum* or *P. aphamidatum*) and *P. oligandrum* on mushrooms; *Ramularia* species, such as *R. collo-cygni* on barley (for *Ramularia* leaf spot, physiological leaf spot), *R. areola* on cotton (sexual form: *Mycosphaerella areola*), and *R. beticola* on sugar beet; *Rhizoctonia* species on cotton, rice, potato, grasses, corn, rapeseed, potato, sugar beet, vegetables, and many other plants, such as *R. rhizoctonia* on soybean. * Rhizoctonia solani* (root and stem rot); *Rhizoctonia solani* (sheath blight) on rice; or *Rhizoctonia cerealis* (rhizoctonia solani leaf blight) on wheat or barley; *Rhizopus stolonifer* (black mold, soft rot) on strawberries, carrots, cabbage, vines, and tomatoes; *Rhynchosporium secalis* and *R. commune* (scald) on barley, rye, and triticale; *Sarocladium oryzae* and *S. attenuatum* (sheath rot) on rice; and *S. minor* and *S. attenuatum* (sclerotiorum) on vegetables. *Sclerotiorum* species (stalk rot or white mold) on field crops such as rapeseed, sunflower (e.g., *Sclerotinia*) and soybean; *S. rolfsii* (synonym *Athelia rolfsii*) on soybean, peanut, vegetables, corn, cereals and ornamental plants; *Septoria* species on various plants, such as *S. glycines* (brown spot) on soybean, *S. tritici* (synonym *S. tritici*, leaf blight) on wheat, and *S. glumebaurus* (glycines) on cereals.nodorum (synonym: Stagonospora nodorum, Stagonospora blotch); Uncinula necator on vines (synonym: Erysiphe necator) (powdery mildew, asexual form: Oidium tuckeri); Setosphaeria species on corn (e.g., S. turcicum, synonym: Helminthosporium turcicum) and turfgrass (leaf blight); S. reiliana on corn (e.g., Ustilago reiliana: corn smut), Sphacelotheca species on sorghum and sugarcane (smut); Sphaerotheca on cucurbits. *Fulginea* (synonym: *Podosphaera xanthii*: powdery mildew); *Spongospora subterranea* on potatoes (powdery mildew) and the viral diseases transmitted by it; *Stagonospora* species on cereals, such as *S. nodorum* on wheat (sex form: *Leptosphaeria nodorum* [synonym: *Phaeosphaeria nodorum*], synonym: *Septoria nodorum*); *Synchytrium endobioticum* on potatoes (potato canker); *Taphrina* species, such as *T. deformans* on peaches (leaf curl) and *T. plum* on plum trees. *Prunus pruni* (plum pocket disease); *Thielaviopsis* species (black root rot) on tobacco, pome, vegetables, soybeans, and cotton, such as *T. basicola* (synonym *Chalara elegans*); *Tilletia* species (wheat smut or wheat smut) on cereals, such as *T. tritici* (synonym *T. caries*, wheat smut) and *T. dwarf smut* (*T. tritici*).(controversa) wheat dwarf smut; Trichoderma harzianum on mushrooms; Typhula incarnata on barley or wheat (grey snow mold); species of the genus Urocystis, such as U. occulta on rye (stem smut); species of the genus Uromyces on vegetables (rust), such as U. appendiculatus (e.g., U. phaseoli), U. beae (e.g., U. beticola), and U. vignae, U. pisi, U. pisi, and U. pisi. *Ustilago* species (loosesmut) on cereals (e.g., *Ustilago nuda* and *Ustilago avaenae*), maize (e.g., *Ustilago maydis*: maize smut), and sugarcane; *Venturia* species (scab) on apples (e.g., *V. inaequalis*) and pears; and *Verticillium* species (wilt) on various plants such as fruits and ornamental plants, vines, berries, vegetables, and field crops, such as *V. longisporum* on rapeseed, *V. dahliae* on strawberries, rapeseed, potatoes, and tomatoes, and *V. fungicola* on mushrooms; and *Syngonium faberi* on cereals.

[0086] Preferably, the binary composition and its agrochemical composition according to the present invention are used to control the following pathogenic factors of plant diseases: Alternaria species (Alternaria dauci or Alternaria porri) on vegetables, rapeseed (Alternaria brassicicola or Alternaria brassicae), rice, soybean, potato and tomato (e.g. Alternaria solanacea, Alternaria citrinum or Alternaria alternata) and Alternaria species (Alternaria leaf spot) on tomatoes (e.g. Alternaria solanacea or Alternaria alternata); Bipolaris species and Drechslera species (sexual form: Cochliobolus species), such as small leaf spot (D. maydis) or large leaf spot (B. maydis) on maize. zeicola); corn (e.g., gray leaf spot: Cercospora zeae-maydis), soybean (e.g., Cercospora zeae-maydis). Cercospora species on *Cercospora sojina* or *C. kikuchii* (Cercospora leaf spot); Cochliobolus species (asexual form: *Helminthosporium* of *Bipolaris*) on corn (C. carbonum) (leaf spot); Coryne-spora cassiicola on soybean (leaf spot); *Helminthosporium* species (synonym: *Helminthosporium*) on corn (e.g., *C. zearalenium*); Fusarium species (sexual form: *Gibberella*) on various plants (wilt, root or stem rot), such as *Fusarium graminearum* on cereals (e.g., wheat or barley). *Fusarium graminearum* or *F. culmorum* (root rot, scab, or wilt), *F. oxysporum* on tomatoes, *F. solani* (a soybean-specific strain, now synonymous with *F. virguliforme*) and *F. tucumaniae* (the South American soybean sudden death syndrome pathogen), as well as *F. brasiliense*, and *F. moniliforme* on corn.verticillioides; *Microsphaeradiffusa* (a type of powdery mildew) on grains (e.g., wheat or barley); *Microsphaeradiffusa* (powdery mildew) on soybeans; *Mycosphaerella* species on grains, bananas, berries, and peanuts, such as *M. graminicola* (asexual form: *Zymoseptoriatritici*, formerly *Septoria tritici*: leaf spot) on wheat, or *M. fijiensis* (a type of black leaf spot) on bananas, *Pseudocercospora fijiensis* (a type of black leaf spot) on soybeans, *P. meibomiae* (soybean rust); *Phoma lingam* (a type of black shank fungus) and *Leptosphaeria biglobosa* (a type of black shank fungus) on rapeseed. Maculans: root and stem rot); Phytophthora infestans on potatoes and tomatoes: late blight; Puccinia species (rust) on various plants, such as P. triticina (brown rust or leaf rust), P. striiformis (stripe rust or yellow rust), P. hordei (dwarf rust), P. graminis (stem rust or black rust) or P. recondita (brown rust or leaf rust) on cereals, P. sorghi (common rust) and P. pollysora (southern rust) on maize; on various crops; Pythium species (dampness-causing) Sclerotinia sclerotiorum; Pyrenophora Net blotch on plants (Septoria); *Septoria* species on various plants, such as *S. glycines* on soybeans (brown spot disease) and *S. tritici* on wheat (synonyms: *S. tritici*, *S. tritici* leaf blight).

[0087] According to a preferred embodiment of the invention, compositions M.1 to M.680 are used to control Alternaria species (Alternaria leaf spot) on vegetables (e.g., Alternaria dauci or Alternaria porri), rapeseed (Alternaria brassicicola or Alternaria brassicae), rice, soybean, potato and tomato (e.g. Alternaria solanacea, Alternaria citrifolia or Alternata alternata) and tomatoes (e.g. Alternaria solanacea or Alternata alternata).

[0088] According to another preferred embodiment of the invention, compositions M.1 to M.680 are used to control species of the genera *Bipolaris* and *Drechslera* (sexual form: *Cochliobolus* species), such as small leaf spot (*D. maydis*) or large leaf spot (*B. zeicola*) on maize.

[0089] According to another preferred embodiment of the invention, compositions M.1 to M.680 are used to control Cercospora species (Cercospora leaf spot) on maize (e.g., gray leaf spot: Cercospora zeae-maydis) and soybean (e.g., Cercospora sojina or Cercospora kikuchii)).

[0090] According to another preferred embodiment of the invention, compositions M.1 to M.680 are used to control rice blast fungus (Pyricularia oryzae) (synonym Magnaphorthe oryzae).

[0091] According to another preferred embodiment of the invention, compositions M.1 to M.680 are used to control leaf spot disease of *C. carbonum* species (asexual form: *Helminthosporium* of *Bipolaris*) on maize.

[0092] According to another preferred embodiment of the invention, compositions M.1 to M.680 are used to control Coryne-spora cassiicola (leaf spot disease) on soybeans.

[0093] According to another preferred embodiment of the invention, compositions M.1 to M.680 are used to control *Helixomyces* species (synonyms *Helixomyces*) on maize (e.g., maize leaf spot pathogen).

[0094] According to another preferred embodiment of the invention, compositions M.1 to M.680 are used to control various Fusarium species (sexual form: Gibberella) on plants (wilt, root or stem rot), such as Fusarium graminearum or Fusarium culmorum on cereals (e.g., wheat or barley) (root rot, scab, or wilt), Fusarium oxysporum on tomatoes, Fusarium solani (a soybean-specific strain, now synonymous with Fusarium virguliforme) and Fusarium tucumaniae (the South American soybean sudden death syndrome pathogen) and Fusarium brasiliense on soybeans, and Fusarium verticillioides on corn.

[0095] According to another preferred embodiment of the invention, compositions M.1 to M.680 are used to control Microdochium nivale (synonym Fusarium nivale) (powdery mildew) on grains (e.g., wheat or barley).

[0096] According to another preferred embodiment of the invention, compositions M.1 to M.680 are used to control the spread of Microsphaera diffusa (powdery mildew) on soybeans.

[0097] According to another preferred embodiment of the invention, compositions M.1 to M.680 are used to control Mycosphaerella species on grains, bananas, berries and peanuts, such as Mycosphaerella graminicola on wheat (asexual form: Zymoseptoria tritici, formerly known as Septoria tritici: leaf spot) or Mycosphaerella fijiensis on bananas (synonym Pseudocercospora fijiensis: black leaf spot).

[0098] According to another preferred embodiment of the invention, compositions M.1 to M.680 are used to control Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans.

[0099] According to another preferred embodiment of the invention, compositions M.1 to M.680 are used to control Phona lingam (synonyms Leptosphaeria biglobosa and L. maculans: root and stem rot) on rapeseed.

[0100] According to another preferred embodiment of the invention, compositions M.1 to M.680 are used to control Phytophthora infestans, a pathogenic blight, on potatoes and tomatoes.

[0101] According to another preferred embodiment of the invention, compositions M.1 to M.680 are used to control various species of *Puccinia* (rust) on plants, such as *P. triticina* (brown rust or leaf rust), *P. striiformis* (stripe rust or yellow rust), *P. hordei* (dwarf rust), *P. graminis* (stem rust or black rust), or *P. recondita* (brown rust or leaf rust) on cereals, and *P. sorghi* (common rust) and *P. pollysora* (southern rust) on maize; on various crops.

[0102] According to another preferred embodiment of the invention, compositions M.1 to M.680 are used to control net blotch disease on *Sclerotinia sclerotiorum*, a species of *Pythium*, and *Pyrenophorateres*.

[0103] According to another preferred embodiment of the invention, compositions M.1 to M.680 are used to control various Septoria species on plants, such as S. glycines on soybean (brown spot disease) and S. tritici on wheat (synonyms: S. tritici, Septoria leaf blight).

[0104] In one aspect of the invention, the amount of compounds I-1 to I-4 in compositions M.1 to M.680 is between 40 and 150 g / ha, preferably between 50 and 100 g / ha.

[0105] In one aspect of the invention, the amount of compounds II-1 to II-34 is 20 to 300 g / ha, preferably 50 to 200 g / ha.

[0106] The binary compositions and agrochemical compositions according to the invention may also be used as fungicides in the form of premixes with other active substances (e.g., with herbicides, insecticides, growth regulators, fungicides or otherwise with fertilizers), or, if appropriate, until immediately before use (tank mix).

[0107] In many cases, mixing active compounds I and II, as well as compositions comprising the compositions, in their intended form as fungicides with other fungicides results in an expansion of the fungicidal activity spectrum or prevents the development of fungicide resistance. Furthermore, synergistic effects are often observed.

[0108] The binary compositions according to the invention can be converted into commonly used types of agrochemical compositions, such as solutions, emulsions, suspensions, dusts, powders, pastes, granules, tablets, capsules, and combinations thereof. Examples of composition types are suspensions (e.g., SC, OD, FS), emulsifiable concentrates (e.g., EC), emulsions (e.g., EW, EO, ES, ME), capsules (e.g., CS, ZC), pastes, tablets, wettable powders or dusts (e.g., WP, SP, WS, DP, DS), tablets (e.g., BR, TB, DT), granules (e.g., WG, SG, GR, FG, GG, MG), insecticides (e.g., LN), and gel formulations for treating plant propagation materials such as seeds (e.g., GF). These and other composition types are defined in “Catalogue of pesticide formulation types and international coding system”, Technical Monograph, Vol. 2, 6th edition, May 2008, CropLife International.

[0109] These compositions are prepared in known ways, as described in: Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.

[0110] The binary compositions of the active compounds described herein can be prepared by conventional means, such as those given herein for the composition of compound I, into compositions comprising at least one inert component (adjuvant) in addition to the active ingredient. For the general composition of such compositions, refer to the explanation given for the composition containing compound I.

[0111] Suitable additives include solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, auxiliary agents, solubilizers, penetration enhancers, protective colloids, adhesives, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, antifreeze agents, defoamers, colorants, viscous agents, and adhesives.

[0112] Agricultural chemical compositions typically contain between 0.01% and 95% by weight, preferably between 0.1% and 90%, more preferably between 1% and 70%, and particularly between 10% and 60% of an active substance. The active substance is used with a purity of 90% to 100%, preferably 95% to 100% (based on NMR spectra).

[0113] For the purpose of treating plant propagating material, especially seeds, seed treatment solutions (LS), suspension emulsions (SE), flowable concentrates (FS), dry treatment powders (DS), water-dispersible powders (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC), and gels (GF) are commonly used. After dilution two to ten times, the concentration of the active compound in the ready-to-use formulation of the compositions under discussion is 0.01% to 60% by weight, preferably 0.1% to 40%. Application can be carried out before or during sowing. Methods for applying compound I and its compositions separately to plant propagating material, especially seeds, include seed dressing, coating, granulation, dusting, soaking, and furrow application. Preferably, the binary composition or its composition according to the invention is applied to the plant propagating material by methods that do not induce germination, such as seed dressing, granulation, coating, and dusting.

[0114] When used for plant protection, the amount of active substance applied is 0.001 to 2 kg / ha, preferably 0.005 to 2 kg / ha, more preferably 0.05 to 0.9 kg / ha, and especially 0.1 to 0.75 kg / ha, depending on the type of effect desired.

[0115] In the treatment of plant propagation material such as seeds, for example by dusting, coating or soaking, the amount of active compound is typically required for every 100 kg of plant propagation material (preferably seeds), ranging from 0.1 to 1000 g, preferably 1 to 1000 g, more preferably 1 to 100 g, and most preferably 5 to 100 g.

[0116] When used for the protection of materials or stored products, the amount of active compound applied depends on the type of application and the desired effect. Typically, the amount applied for the protection of materials is 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active compound per cubic meter of treated material.

[0117] By applying the binary composition according to the invention, a synergistic effect can be obtained, that is, a simple summation of more than a single effect (synergistic composition).

[0118] This can be achieved by applying the binary composition according to the invention in combination (e.g., as a barrel mix) or separately, or sequentially, wherein the time interval between individual applications is chosen to ensure that the initially applied active compound remains present at the site of action in sufficient quantity when the other active substance is applied. The order of application is not important for the implementation of the invention.

[0119] When the binary composition according to the invention is applied sequentially, the time between two applications can vary, for example, from 2 hours to 7 days. A range of 0.25 hours to 30 days, preferably 0.5 hours to 14 days, particularly 1 hour to 7 days or 1.5 hours to 5 days, and even more preferably a wider range of 2 hours to 1 day is also possible.

[0120] Biological testing

[0121] Microtest

[0122] The active compound was prepared separately as a stock solution with a concentration of 10,000 ppm in dimethyl sulfoxide.

[0123] Mix the stock solution according to the specified ratio, transfer it to a microtiter plate (MTP) using a pipette, and dilute it with water to the specified concentration.

[0124] Example 1 - Activity against Pyricularia oryzae in microtiter plate test

[0125] Then add the spore suspension of *Pyroxburghii* in a biological malt aqueous solution or a yeast-bacterial peptone-sodium acetate solution.

[0126] These plates were placed in a water vapor saturated chamber at 18°C. MTP was measured at 405 nm using an absorbance spectrophotometer 7 days post-inoculation.

[0127] The measured parameters were compared with the growth rate (100%) of the control variant of the inactive compound and the fungal-free blank value to determine the relative growth rate (in percentage) of pathogens in the corresponding active compound. These percentages were then converted into efficacy.

[0128] Efficacy 0 means that the growth level of the pathogen corresponds to the growth level of the untreated control; efficacy 100 means that the pathogen did not grow.

[0129] The expected efficacy of the active compound mixture was determined using the Colby formula [RS Colby, “Calculating synergistic and antagonistic responses of herbicide combinations]].

[0130]

[0131] Example 2 - Anti-Septoria tritici activity in microtiter plate test

[0132] Then add a spore suspension of wheat husk spores in a biological malt aqueous solution or a yeast-bacterial peptone-sodium acetate solution.

[0133] These plates were placed in a water vapor saturated chamber at 18°C. MTP was measured at 405 nm using an absorbance spectrophotometer 7 days post-inoculation.

[0134] The measured parameters were compared with the growth rate (100%) of the control variant of the inactive compound and the fungal-free blank value to determine the relative growth rate (in percentage) of pathogens in the corresponding active compound. These percentages were then converted into efficacy.

[0135] Efficacy 0 means that the growth level of the pathogen corresponds to the growth level of the untreated control; efficacy 100 means that the pathogen did not grow.

[0136] The expected efficacy of the active compound mixture was determined using the Colby formula [RS Colby, “Calculating synergistic and antagonistic responses of herbicide combinations]].

[0137] .

Claims

1. A fungicidal composition comprising, as active ingredient 1), at least one compound selected from the group consisting of: (I-1) (Z)-2-(5-cyclobutyl-2-methylphenoxy)-3-methoxy-prop-2-enoic acid methyl ester (I-2) (Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxy-prop-2-enoic acid methyl ester (I-3) (Z)-2-(5-cyclopropyl-2-methylphenoxy)-3-methoxy-prop-2-enoic acid methyl ester (I-4) (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxy-prop-2-enoic acid methyl ester As active ingredient 2), at least one compound selected from the group consisting of, or its N-oxide, or an agriculturally useful salt. (II-1) Flusulfanilamide (II-2) Fluopyram (II-3) Fluopyridazine (II-4) Trifluoropyridine (II-5) Methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propionate (II-6) 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propionic acid (II-7) 1-[[4-[5-[chloro(difluoro)methyl]-1,2,4-oxadiazol-3-yl]-2-fluoro-phenyl]methyl]pyrazole-4-carboxylic acid ethyl ester (II-8) 1-[[5-[5-[chloro(difluoro)methyl]-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylic acid ethyl ester (II-9) 5-[chloro(difluoro)methyl]-3-[4-[(3-ethynylpyrazol-1-yl)methyl]phenyl]-1,2,4-oxadiazole (II-10) 1-[[4-[5-[chloro(difluoro)methyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]-1,3-dimethoxy-urea (II-11) N-[[4-[5-[chloro(difluoro)methyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]-N,2-dimethoxy-propionamide (II-12) 2-(4-fluorophenoxy)-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl ketone (II-13) 2-[(6-fluoro-3-pyridyl)oxy]-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetone (II-14) 2-(4-fluoroanilino)-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ketene (II-15) N-[1-[[3-[2-(5-fluoro-2-methoxy-phenyl)-2-hydroxy-ethyl]-5-[(Z)-N-isopropoxy-C-methyl-carboimino]-2,6-dioxo-pyrimidin-1-yl]methyl]-2-methyl-propyl]-2-methyl-propionamide (II-16) N-[1-[[3-[2-(5-fluoro-2-methoxy-phenyl)-2-hydroxy-ethyl]-5-[(Z)-N-isopropoxy-C-methyl-carboimino]-2,6-dioxo-pyrimidin-1-yl]methyl]-2-methyl-propyl]-2,2-dimethyl-propionamide (II-17) N-[2-[3-[2-(5-fluoro-2-methoxy-phenyl)-2-hydroxy-ethyl]-5-[(Z)-N-isopropoxy-C-methyl-carboimino]-2,6-dioxo-pyrimidin-1-yl]-1-methyl-ethyl]-2-methyl-propionamide (II-18) N-[2-[3-[2-hydroxy-2-(2-methoxyphenyl)ethyl]-5-[(Z)-N-isopropoxy-C-methyl-carboimino]-2,6-dioxo-pyrimidin-1-yl]-1-methyl-ethyl]-2-methyl-propionamide (II-19) N-[2-[3-[2-(2-cyanoethoxy)-2-(5-fluoro-2-methoxy-propyl)ethyl]-5-[(Z)-N-isopropoxy-C-methyl-carboimino]-2,6-dioxo-pyrimidin-1-yl]-1-methyl-ethyl]-2-methyl-propionamide (II-20) 3-[3-(3-chloro-2-fluoro-phenoxy)-6-methyl-pyridazin-4-yl]-5-[(2-chloro-4-methyl-phenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine (II-21) (5S)-3-[3-(3-chloro-2-fluoro-phenoxy)-6-methyl-pyridazin-4-yl]-5-[(2-chloro-4-methyl-phenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine (II-22) (5R)-3-[3-(3-chloro-2-fluoro-phenoxy)-6-methylpyridazin-4-yl]-5-[(2-chloro-4-methyl-phenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine (II-23) 1-[4-[4-[5-(2,6-dichlorophenyl)-4,5-dihydroisoxazo-3-yl]thiazo-2-yl]-1-piperidinyl]-2-[3-(trifluoromethyl)pyrazin-2-yl]oxy-acetone (II-24) 1-[4-[4-[5-(2-chloro-6-fluoro-phenyl)-4,5-dihydroisoxazo-3-yl]thiazo-2-yl]-1-piperidinyl]-2-[[3-(trifluoromethyl)-2-pyridinyl]oxy]ethenone (II-25) 4-[4-[5-(2-bromo-6-fluoro-phenyl)-4,5-dihydroisoxazol-3-yl]thiazolyl-2-yl]piperidine-1-carboxylic acid tert-butyl ester (II-26) ((2-(3-(2-(1-(2-(3,5-bis(trifluoromethyl)-1H-pyrazole-1-yl)acetyl)piperidin-4-yl)thiazo-4-yl)-4,5-dihydroisoxazol-5-yl)-3-fluorophenyl)imino)dimethyl-λ6-sulfonone) (II-27) ((2-(3-(2-(1-(2-(3,5-bis(difluoromethyl)-1H-pyrazol-1-yl)acetyl)piperidin-4-yl)thiazo-4-yl)-4,5-dihydroisoxazol-5-yl)-3-fluorophenyl)imino)dimethyl-λ6-sulfonone) (II-28) ((2-(3-(2-(1-(2-(3,5-bis(difluoromethyl)-1H-pyrazol-1-yl)acetyl)piperidin-4-yl)thiazo-4-yl)-4,5-dihydroisoxazol-5-yl)-3-chlorophenyl)imino)(isopropyl)(methyl)-λ6-sulfonone (II-29) ((2-(3-(2-(1-(2-(3,5-bis(trifluoromethyl)-1H-pyrazole-1-yl)acetyl)piperidin-4-yl)thiazo-4-yl)-4,5-dihydroisoxazol-5-yl)-3-fluorophenyl)imino)(isopropyl)(methyl)-λ6-sulfonone (II-30) ((2-(3-(2-(1-(2-(3,5-bis(difluoromethyl)-1H-pyrazol-1-yl)acetyl)piperidin-4-yl)thiazo-4-yl)-4,5-dihydroisoxazol-5-yl)-3-(trifluoromethyl)phenyl)imino)dimethyl-λ6-sulfonone (II-31) ((3-fluoro-2-(3-(2-(1-(2-(5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetyl)piperidin-4-yl)thiazo-4-yl)-4,5-dihydroisoxazol-5-yl)phenyl)imino)dimethyl-λ6-sulfonone) (II-32) N-(1-benzyl-1,3-dimethylbutyl)-8-fluoroquinoline-3-carboxamide (II-33) N-[(1R)-1-benzyl-1,3-dimethylbutyl]-8-fluoroquinoline-3-carboxamide (II-34) N-[(1S)-1-benzyl-1,3-dimethylbutyl]-8-fluoroquinoline-3-carboxamide The weight ratio of compound I to compound II is 10:1 to 1:

10.

2. The composition according to claim 1, wherein, Active component a) is selected from the group consisting of (I-2) and (I-4).

3. The composition according to claim 1 or 2, wherein, Active component 2) is selected from the following groups: (II-1), (II-2), (II-3), (II-4), (II-7), (II-8), (II-9), (II-10), (II-11), (II-20), (II-21), (II-22), (II-23), (II-26), (II-29), (II-32), (II-33), (II-34).

4. The composition according to any one of claims 1 to 3, comprising compound I and compound II in a weight ratio of 3:1 to 1:

3.

5. The composition according to any one of claims 1 to 3, comprising compound I and compound II in a weight ratio of 2:1 to 1:

2.

6. An agricultural chemical composition comprising a solvent or solid carrier and the composition according to any one of claims 1 to 5.

7. The agricultural chemical composition according to claim 6, further comprising seeds in an amount of 1 g to 1000 g of active ingredient per 100 kg of seeds.

8. The composition according to any one of claims 1 to 7 for non-therapeutic use in controlling plant pathogenic harmful fungi.

9. The non-therapeutic use according to claim 8, for controlling plant pathogenic harmful fungi on the following plants: wheat, such as common wheat (spring wheat, winter wheat and intermediate wheat), spring barley and winter barley (barley), spring triticale and winter triticale; corn (maize); legumes, such as lentils (lentils, lentils), soybeans (cultivated soybeans, hairy soybeans) and common beans (peas), such as dried beans or field beans and fresh beans, including kidney beans, green beans, string beans, common beans (common beans, dwarf common beans); oilseed plants, such as spring rapeseed and winter rapeseed (European rapeseed), canola rapeseed (European rapeseed and turnip) or sunflowers (sunflowers); tomatoes (yellow cherries, also known as cherry tomatoes), potatoes (potatoes).

10. The non-therapeutic use according to any one of claims 8 to 9, for controlling diseases selected from the group consisting of: Alternaria species (Alternaria carata or Alternaria allium), rapeseed (Alternaria brassicae or Alternaria brassicae), rice, soybean, potato, and tomato (e.g., Alternaria solanacea, Alternaria citrinum, or Alternaria alternifolia), and tomato (e.g., Alternaria solanacea or Alternaria alternifolia) (Alternaria leaf spot); Helicobacterium species and Helicobacterium species (sexual form: Helicobacterium species), such as small leaf spot (Helicobacter spp.) or large leaf spot (Helicobacter spp.) on maize; maize (e.g., gray leaf spot: Cercospora zeylanica), soybean (e.g., Cercospora davidii). Cercospora species on soybean (Cercospora purpureus) (Cercospora leaf spot); *Cercospora* species (asexual form: *Helicobacter* genus) on corn (*Cercospora charcoalensis*) (leaf spot); *Cyclospora spp.* on soybean (leaf spot); *Helicobacter* species (synonym: *Helicobacter* genus) on corn (e.g., *Helicobacter* var. *maize*); *Fusarium* species (sexual form: *Fusarium* genus) on various plants (wilt, root or stem rot), such as *Fusarium graminearum* or *Fusarium graminearum* on grains (e.g., wheat or barley) (root rot, scab, or wilt), *Fusarium oxysporum* on tomatoes, and *Fusarium solani* on soybeans that cause sudden death syndrome (soybean-specific, now synonymous with *Fusarium solani*). Fungi) and the South American soybean sudden death syndrome pathogen, as well as *Fusarium brasiliensis*, and *Fusarium moniliforme* on corn; *Microsporum nivale* (synonym *Fusarium nivale*) on grains (such as wheat or barley) (powdery mildew); *Pseudomonas diffusa* (powdery mildew) on soybeans; *Cyclophorus* species on grains, bananas, berries, and peanuts, such as *Cyclophorus spp.* (asexual form: *Synonymyxophorus spp.*, formerly known as *Synonymyxophorus spp.*: leaf spot) or *Cyclophorus spp.* (synonym *Pseudocereus spp.*: black leaf spot) on bananas; *Laminaria japonica* and *Laminaria spp.* (soybean rust) on soybeans; *Pseudomonas spp.* (black shank rust) on rapeseed (synonym *Pseudomonas spp.*: root and stem rot); *Cyclophorus spp.* on potatoes and tomatoes. Phytophthora: Late blight; rust species (rusts) on various plants, such as *Phytophthora leuciscus* (brown rust or leaf rust), *Phytophthora striata* (stripe rust or yellow rust), *Phytophthora barley* (dwarf rust), *Phytophthora graminea* (stem rust or black rust), or *Phytophthora cryptica* (brown rust or leaf rust) on cereals, *Phytophthora sorghum* (common rust) and *Phytophthora multidus* (southern rust) on maize; on various crops; *Pythium* species (dampness-causing) *Sclerotinia*; net blotch on *Phytophthora barley*; *Synonyms* species on various plants, such as *Synonyms sacchari* (brown spot) on soybeans, and *Synonyms sacchari* (synonyms: *Synonyms sacchari*, *Synonyms sacchari* leaf blight) on wheat.

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