Antifungal components

Abstract

A composition suitable for controlling diseases caused by plant pathogens, comprising: (A) a compound of formula I TIFF2023515168000026.tif61132 (in the formula, R 1 and R 2 are each independently halogen, cyano, or C1-C3 haloalkyl, and R 3 is hydrogen, C1-C3 alkyl, C1-C3 alkenyl, or C1-C3 alkynyl, A is CH or N, and X is CH2, C(=O), O, or S). and (B) a composition comprising at least one compound selected from compounds known for their fungicidal activity; and a method for controlling diseases, particularly leaf spot diseases in cereals, on useful plants.

Description

[Technical Field]

[0001] The present invention relates to novel fungicidal compositions suitable for controlling diseases caused by plant pathogens, in particular plant pathogenic fungi, and to methods for controlling diseases on useful plants, in particular fruits and vegetables. [Background technology]

[0002] WO 2019 / 093522 discloses that certain 2-hydroxypropanoate derivatives and mixtures containing the 2-hydroxypropanoate derivatives have biological activity against plant pathogenic fungi. Meanwhile, various fungicidal compounds of different chemical classes are widely known as plant fungicides for use in various harvests of cultivated plants. However, their crop tolerance and activity against plant pathogenic fungi do not always meet the needs of agricultural practice in many cases and aspects. In particular, pathogens causing leaf spot diseases such as Mycosphaerella arachidis, the causal agent of peanut leaf spot disease; Corynespora casiicola, the causal agent of target spot disease on tomato and soybean; Septoria species causing leaf spot on a wide range of important crops such as wheat and soybean; and powdery fungi such as Uncinula necator, the causal agent of powdery mildew and blight on grapes; and Botrytis cinerea, the causal agent of gray mold disease on various crop plants, are becoming an increasingly important problem in crop production, resulting in significant yield losses. Many conventional fungicides are either unsuitable for controlling leaf spot, powdery mildew and grey mold, or their activity against Septoria species such as Zymoseptoria tritici, Septoria glycines, Uncinula necator and Botrytis cinerea is unsatisfactory. Summary of the Invention [Means for solving the problem]

[0003] Therefore, in view of the above-mentioned demands of agricultural practice for increased crop tolerance and / or increased activity against plant pathogenic fungi, such as leaf spot, powdery mildew and mould, the present invention provides novel compositions suitable for controlling diseases caused by plant pathogens, comprising: (A) Formula I [ka] (In the formula, R 1 and R 2 are each independently halogen, cyano, or C1-C3 haloalkyl, and R 3 is hydrogen, C1-C3 alkyl, C1-C3 alkenyl, or C1-C3 alkynyl, A is CH or N, and X is CH2, C(=O), O, or S). Compounds of; and (B) at least one compound selected from the group consisting of benzothiostrobin, cyclobutrifluram, and florilpi; KoN-(2-chloro-5-methyl-4-phenoxyphenyl)-N-ethyl-N-methyl-formamidine, N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl] ... -phenyl]-N-ethyl-N-methyl-formamidine, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl 1-(5,6-dimethyl-3-pyridyl)-4,4-difluoro-3,3-dimethyl-isoquinoline, 1-[6-(difluoromethyl)-5-methyl-3-pyridyl]-4,4-difluoro-3,3-dimethyl-isoquinoline, 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2, 4-Oxadiazol-3-yl]phenyl]acetamide, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide, [1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, [1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, 2,at least one compound selected from the group consisting of 2-difluoro-N-[6-[[1-(1-methyltetrazol-5-yl)benzimidazol-2-yl]oxymethyl]-2-pyridyl]-2-phenoxy-acetamide, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile, and 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile, A novel composition is proposed comprising: DETAILED DESCRIPTION OF THE INVENTION

[0004] The presence of one or more asymmetric carbon atoms in the compounds of formula I means that the compounds can exist in optically isomeric, i.e., enantiomeric or diastereomeric, forms. Conformational isomers may also exist as a result of restricted rotation about a single bond. The present invention encompasses all such possible isomeric forms of the compounds of formula I and mixtures thereof. Similarly, formula I is intended to include all possible tautomers. The present invention includes all possible tautomeric forms of the compounds of formula I as well as racemates, i.e., mixtures of at least two enantiomers in a substantially 50:50 ratio.

[0005] In each case, the compounds of formula I according to the invention are in free form, in oxidized form, such as N-oxide, or in salt form, for example in the form of an agriculturally usable salt.

[0006] N-oxides are oxidized forms of tertiary amines or nitrogen-containing heteroaromatic compounds. They are described, for example, in the book "Heterocyclic N-oxides" by A. Albini and S. Pietra, CRC Press, Boca Raton 1991.

[0007] A preferred composition is (A) Formula I [ka] (In the formula, R 1 and R 2 are, independently of each other, fluoro, chloro or trifluoromethyl; R 3 is methyl or ethyl, A is N, and X is C(=O) or O) Compounds of; and (B) at least one compound, Ko oxamide, fluveneteram, fluopimomide, fluoxapiprolin, ipflufenoquin, mandestrobin, methyltetraprole, pyriophenone, pyrisoxazole, 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide, N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3 -enamide, 1-(5,6-dimethyl-3-pyridyl)-4,4-difluoro-3,3-dimethyl-isoquinoline, 1-[6-(difluoromethyl)-5-methyl-3-pyridyl]-4,4-difluoro-3,3-dimethyl-isoquinoline, 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide, [1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate It includes:

[0008] It has been discovered that using component (B) in combination with component (A) surprisingly and significantly increases the effectiveness of the latter against fungi, and vice versa. Furthermore, the method of the present invention is effective against a broader spectrum of such fungi than can be controlled by the active ingredients of the method when used alone.

[0009] A further aspect of the present invention is a method for controlling diseases caused by plant pathogens on useful plants or their propagation material, comprising applying a composition according to the present invention to the useful plant, its locus or its propagation material. Preferred is a method comprising applying a composition according to the present invention to the useful plant or its locus, more preferably to the useful plant. Even more preferred is a method comprising applying a composition according to the present invention to the propagation material of a useful plant. The present invention covers all stereoisomers and mixtures thereof in all ratios.

[0010] A preferred embodiment of the present invention is that component A) is a compound in which A is N and X is O, most preferably R 1 is chloro and R 2 is chloro and R 3 is methyl, A is N, and X is O, or R 1 is chloro and R 2 is chloro and R 3 is ethyl, A is N, and X is O, or R 1 is chloro and R 2 is trifluoromethyl and R 3is methyl, A is N, and X is O. These preferred compounds of formula (I) are methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoate (Compound A-1.1); ethyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoate (Compound A-1.2); and methyl 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoate (Compound A-1.3).

[0011] A further preferred embodiment of the present invention is a compound comprising, as component B), florilpi Kooxamide, fluveneteram, fluopimomide, fluoxapiprolin, ipflufenoquin, mandestrobin, methyltetraprole, pyriophenone, pyrisoxazole, 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide, N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3- enamide, 1-(5,6-dimethyl-3-pyridyl)-4,4-difluoro-3,3-dimethyl-isoquinoline, 1-[6-(difluoromethyl)-5-methyl-3-pyridyl]-4,4-difluoro-3,3-dimethyl-isoquinoline, 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide, [1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate.

[0012] Particularly preferred compositions according to the invention comprise, as component (A), a compound selected from methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoate (compound A-1.1), ethyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoate (compound A-1.2) and methyl 2-[4methyl-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoate (compound A-1.3), and, as component (B), florylpyrrolidone. Kooxamide, fluveneteram, fluopimomide, fluoxapiprolin, ipflufenoquin, mandestrobin, methyltetraprole, pyriophenone, pyrisoxazole, 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide, N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl- and a compound selected from the group consisting of acetoxy-4-methoxy-3-enamide, 1-(5,6-dimethyl-3-pyridyl)-4,4-difluoro-3,3-dimethyl-isoquinoline, 1-[6-(difluoromethyl)-5-methyl-3-pyridyl]-4,4-difluoro-3,3-dimethyl-isoquinoline, 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide, [1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate.

[0013] Compounds of formula (I) can be prepared by methods similar to those outlined in WO 2019 / 093522 using chemical reactions known in the art.

[0014] Component (B) is known. Most of the components (B) are referred to above by their so-called "ISO common names" or by other "generic names" or trade names used in individual cases.

[0015] The following preferred ingredients (B) are included in the Pesticide Manual Online by the British Crop Production Council ("E-Pesticide Manual") and in the Compendium of Pesticide Common Names by Alan Wood: benzothiostrobin, cyclobutrifluram, florilpi Ko oxamide, fluveneteram, fluopimomide, fluoxapiprolin, ipflufenoquin, mandestrobin, methyltetraprole, pyridaclomethyl, pyriophenone, pyrisoxazole.

[0016] 2-(Difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide is disclosed in WO 2019 / 224175.

[0017] N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine is disclosed in WO 2017 / 005710.

[0018] N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine is disclosed in WO 2016 / 202742.

[0019] 2-[6-(4-Bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol is disclosed in WO 2018 / 145921.

[0020] 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol is disclosed in WO 2018 / 145921.

[0021] (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide is disclosed in WO 2013 / 092224.

[0022] (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide is disclosed in WO 2018 / 153707.

[0023] 1-(5,6-Dimethyl-3-pyridyl)-4,4-difluoro-3,3-dimethyl-isoquinoline is disclosed in WO 2017 / 016915.

[0024] 1-[6-(Difluoromethyl)-5-methyl-3-pyridyl]-4,4-difluoro-3,3-dimethyl-isoquinoline is disclosed in WO 2017 / 016915.

[0025] 2,2-Difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide is disclosed in WO 2017 / 076742.

[0026] N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide is disclosed in WO 2017 / 211649.

[0027] [1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate is disclosed in WO 2019 / 173665.

[0028] [1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate is disclosed in WO 2019 / 173665.

[0029] 2,2-Difluoro-N-[6-[[1-(1-methyltetrazol-5-yl)benzimidazol-2-yl]oxymethyl]-2-pyridyl]-2-phenoxy-acetamide is disclosed in WO 2017 / 178819.

[0030] N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide is disclosed in WO 2017 / 174158.

[0031] 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile is disclosed in WO 2016 / 156290.

[0032] 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile is disclosed in WO 2016 / 156290.

[0033] Examples of compounds that are particularly suitable as component (B) are compounds selected from group P below: florilpi KoN-(2-chloro-5-methyl-4-phenoxyphenyl)-N-ethyl-N-methyl-formamidine, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3 -dimethyl-pent-3-enamide, 1-(5,6-dimethyl-3-pyridyl)-4,4-difluoro-3,3-dimethyl-isoquinoline, 1-[6-(difluoromethyl)-5-methyl-3-pyridyl]-4,4-difluoro-3,3-dimethyl-isoquinoline, 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide, [1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate.

[0034] Throughout this specification, the expression "composition" refers to various mixtures or combinations of components (A) and (B), for example, in a single "ready-mix" form, a combination spray mixture made up of separate formulations of a single active ingredient component such as a "tank mix," and the combined use of a single active ingredient when applied sequentially, i.e., one after the other over a reasonably short period of time, such as a few hours or days. The order in which components (A) and (B) are applied is not essential to the practice of the invention.

[0035] Further examples of compositions according to the invention comprising three active ingredients are defined as embodiments E1, E2 and E3.

[0036] Preferred embodiment E1: As used herein, the term "TX1" means "compound A-1.1 plus a compound selected from group P." Preferred examples include the following compositions: benzothiostrobin plus TX1, cyclobutrifluram plus TX1, florilpi KoN-(2-chloro-5-methyl-4-phenoxyphenyl)-N-ethyl-N-methyl-formamidine + TX1, N'-[2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide + TX1, N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine + TX1, N'-[2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide + TX1, N'-[2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide + TX1, N'-[2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide + TX1, N'-[2-(difluoromethyl)-N-ethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine + TX1, N'-[2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide + TX1, N'-[2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide + TX1, N'-[2-(difluoromethyl)-N-ethyl-N-methyl-formamidine + TX1], N'-[2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide ... Chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine + TX1, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol + TX1, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol + TX1, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methyl 2,2-Difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-N-methyl-3-pyridyl]-4,4-difluoro-3,3-dimethyl-isoquinoline + TX1, (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide + TX1, 1-(5,6-dimethyl-3-pyridyl)-4,4-difluoro-3,3-dimethyl-isoquinoline + TX1, 1-[6-(difluoromethyl)-5-methyl-3-pyridyl]-4,4-difluoro-3,3-dimethyl-isoquinoline + TX1, 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-N ... N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide + TX1, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide + TX1, [1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate + TX1, [1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate + TX1, 2,2-Difluoro-N-[6-[[1-(1-methyltetrazol-5-yl)benzimidazol-2-yl]oxymethyl]-2-pyridyl]-2-phenoxy-acetamide + TX1, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX1, 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile + TX1, 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile + TX1.

[0037] Preferred embodiment E2: The term "TX2" means "compound A-1.2 + a compound selected from group P." Preferred examples include the following compositions: benzothiostrobin + TX2, cyclobutrifluram + TX2, florilpi KoN-oxamide + TX2, fluveneteram + TX2, fluopimomide + TX2, fluoxapiprolin + TX2, ipflufenoquin + TX2, mandestrobin + TX2, methyltetraprole + TX2, pyridaclomethyl + TX2, pyriophenone + TX2, pyrisoxazole + TX2, 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide + TX2, N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine + TX2, N'-[2- Chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine + TX2, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol + TX2, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol + TX2, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methyl 2,2-Difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-N-methyl-3-pyridyl]-4,4-difluoro-3,3-dimethyl-isoquinoline + TX2, (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide + TX2, 1-(5,6-dimethyl-3-pyridyl)-4,4-difluoro-3,3-dimethyl-isoquinoline + TX2, 1-[6-(difluoromethyl)-5-methyl-3-pyridyl]-4,4-difluoro-3,3-dimethyl-isoquinoline + TX2, 2,2-Difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-N ... N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide + TX2, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide + TX2, [1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate + TX2, [1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate + TX2, 2,2-Difluoro-N-[6-[[1-(1-methyltetrazol-5-yl)benzimidazol-2-yl]oxymethyl]-2-pyridyl]-2-phenoxy-acetamide + TX2, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX2, 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile + TX2, 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile + TX2.

[0038] Preferred embodiment E3: The term "TX3" means "compound A-1.3 plus a compound selected from group P." Preferred examples include the following compositions: benzothiostrobin + TX3, cyclobutrifluram + TX3, florilpi KoN-(2-chloro-5-methyl-4-phenoxyphenyl)-N-ethyl-N-methyl-formamidine + TX3, N'-[2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide + TX3, N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine + TX3, N'-[2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide + TX3, N'-[2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide + TX3, N'-[2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide + TX3, N'-[2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide + TX3, N'-[2-(difluoromethyl)-N-ethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine ... Chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine + TX3, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol + TX3, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol + TX3, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methyl 2,2-Difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-N-methyl-3-pyridyl]-4,4-difluoro-3,3-dimethyl-isoquinoline + TX3, (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide ... 1-(5,6-dimethyl-3-pyridyl)-4,4-difluoro-3,3-dimethyl-isoquinoline + TX3, 1-[6-(difluoromethyl)-5-methyl-3-pyridyl]-4,4-difluoro-3,3-dimethyl-isoquinoline + TX3, 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-N-methyl-3-pyridyl]-4,4-difluoro-3,3-dimethyl-isoquinoline + TX3, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide + TX3, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide + TX3, [1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate + TX3, [1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate + TX3, 2,2-Difluoro-N-[6-[[1-(1-methyltetrazol-5-yl)benzimidazol-2-yl]oxymethyl]-2-pyridyl]-2-phenoxy-acetamide + TX3, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX3, 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile + TX3, 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile + TX3.

[0039] Embodiments E1, E2 and E3 define compositions according to the invention comprising three active ingredients. In said embodiments, the mixing partner selected from group P must be different from the other mixing partners described. For example, the composition "benzothiostrobin + TX1" means a composition comprising as active ingredients benzothiostrobin, compound A-1.1 and a compound selected from group P. In said composition, the compound selected from group P is different from benzothiostrobin.

[0040] The following compositions are preferred: A composition comprising (A) compound A-1.1 and (B) a compound selected from group P. An example of such a composition is a composition comprising compound A-1.1 and a first compound from group P, which is benzothiostrobin.

[0041] The compositions according to the invention are effective against harmful microorganisms, such as those causing plant pathogenic diseases, in particular plant pathogenic fungi and bacteria.

[0042] The compositions according to the invention are effective against phytopathogenic fungi, in particular those belonging to the following genera: Ascomycetes (e.g. Venturia, Podosphaera, Erysiphe, Monilinia, Mycosphaerella, Uncinula); Basidiomycetes (e.g. Hemileia, Rhizoctonia, Phakopsora, Puccinia, Ustilago, Tilletia); Fungi imperfecti (e.g. Fungi of the genera Hemileia, Rhizoctonia, Phakopsora, Puccinia, Ustilago, Tilletia); imperfecti (also known as Deuteromycetes; e.g., Botrytis, Helminthosporium, Rhynchosporium, Fusarium, Zymoseptoria, Cercospora, Alternaria, Pyricularia, and Schweizeris) Pseudocercosporella; Oomycetes (e.g., Phytophthora, Peronospora, Pseudoperonospora, Albugo, Bremia, Pythium, Pseudosclerospora, Plasmopara).

[0043] According to the invention, "useful plants" typically include the following plant species: grapevines; cereals such as wheat, barley, rye or oats; beets such as sugar beets or fodder beets; fruits such as pome fruits, drupes or soft fruits, for example apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries or blackberries; legumes such as beans, lentils, peas or soybeans; oil plants such as rapeseed, oilseed rape, poppy, olive, sunflower, coconut, castor bean, cocoa bean or peanut; pumpkin, cucumber plants such as cucumber or melon; fibrous plants such as cotton, flax, hemp or jute; citrus fruits such as orange, lemon, grapefruit or mandarin; vegetables such as spinach, lettuce, asparagus, cabbage, carrot, onion, tomato, potato, cucurbit or pepper; camphor trees such as avocado, cinnamon or camphor; corn; tobacco; nuts; coffee; sugarcane; tea; vines; hop berries; durian; banana; rubber plants; ornamental plants such as grass or flowers, shrubs, broad-leaved or evergreen plants, e.g., conifers. This list is not intended to be limiting.

[0044] The term "useful plants" is also to be understood as including useful plants which, as a result of conventional breeding or genetic engineering methods, have been made tolerant to herbicides such as bromoxynil or several herbicides (e.g. HPPD inhibitors, ALS inhibitors such as primisulfuron, prosulfuron and trifloxysulfuron, EPSPS (5-enol-pyroyl-shikimate-3-phosphate-synthase) inhibitors, GS (glutamine synthetase) inhibitors or PPO (protoporphyrinogen-oxidase) inhibitors, etc. An example of a crop which has been made tolerant to imidazolinones, such as imazamox, by conventional breeding methods (mutagenesis) is Clearfield® summer rapeseed (canola). Examples of crops that have been made tolerant to herbicides or to several herbicides by genetic engineering methods include glyphosate- and glufosinate-tolerant corn varieties available under the trade names RoundupReady®, Herculex I®, and LibertyLink®.

[0045] The term "useful plants" shall also be understood to include useful plants which have been transformed by the use of recombinant DNA techniques so as to be able to synthesize one or more selectively acting toxins, such as, for example, those known from toxin-producing bacteria, in particular those of the genus Bacillus.

[0046] The term "useful plants" should also be understood to include useful substances that have been transformed by the use of recombinant DNA techniques so as to be able to synthesize antipathogenic substances with selective action, such as, for example, so-called "pathogenesis-related proteins" (PRPs, see, for example, EP-A-0 392 225). Examples of such antipathogenic substances and transgenic plants that are able to synthesize such antipathogenic substances are known, for example, from EP-A-0 392 225, WO 95 / 33818 and EP-A-0 353 191. Methods for producing such transgenic plants are generally known to those skilled in the art and are described, for example, in the above-mentioned publications.

[0047] As used herein, the term "locus" of a useful plant is intended to include the location where the useful plant is growing, the location where plant propagation material of the useful plant is sown, or the location where plant propagation material of the useful plant is placed in the soil. An example of such a location is a field where crops are grown.

[0048] The term "plant propagation material" is understood to refer to reproductive parts of plants, such as seeds, and vegetative material, such as cuttings or tubers, e.g., potatoes, that can be used to propagate plants. For example, seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes, and plant parts may be mentioned. Germinated plants and seedlings that are to be transplanted after germination or emergence from the soil may also be mentioned. These seedlings can be protected by a total or partial treatment by immersion before transplanting. Preferably, "plant propagation material" is understood to refer to seeds.

[0049] In a further aspect, the present application also relates to a plant propagation material coated with a composition according to the invention.

[0050] The compositions of the present invention can also be used in the field of protecting stored articles against fungal attack. According to the present invention, the term "storage articles" is understood to refer to natural substances of plant and / or animal origin, as well as their processed forms, which have been removed from their natural life cycle and for which long-term protection is desired. Plant-based storage articles, such as plants or parts thereof, such as stems, leaves, tubers, seeds, fruits, or grains, can be protected both in their freshly harvested state and in processed forms, such as pre-dried, moistened, crushed, ground, pressed, or roasted. Timber also falls within the definition of storage articles, whether in the form of raw logs, such as building timber, utility poles, and electrical barriers, or in the form of finished products, such as furniture or objects made from wood. Storage articles of animal origin include hides, leather, fur, hair, etc. The compositions of the present invention can prevent adverse effects such as decay, discoloration, or mold. Preferably, "storage goods" is understood to refer to natural substances of plant origin and / or their processed forms, more preferably fruits and their processed forms, such as pome fruits, stone fruits, soft fruits and citrus fruits and their processed forms. In another preferred embodiment of the present invention, "storage goods" is understood to refer to trees.

[0051] Thus, a further aspect of the present invention is a method of protecting a storage article comprising applying to the storage article a composition according to the present invention.

[0052] The composition of the present invention can also be used in the field of protecting industrial products against fungal attack. According to the present invention, the term "industrial products" includes paper; carpet; structures; cooling and heating systems; wallboard; ventilation and air-conditioning systems, etc. Preferably, "industrial products" is understood to refer to wallboard. The composition of the present invention can prevent adverse effects such as corrosion, discoloration, or mold.

[0053] The compositions according to the present invention are effective against Alternaria spp., Ascochyta spp., Botrytis cinerea, Cercospora spp., Claviceps purpurea, Cochliobolus sativus, Colletotrichum spp., Epicoccum spp., Fusarium graminearum, Fusarium moniliforme, Fusarium oxysporum, Fusarium proliferatum, Fusarium solani, Fusarium subglutinans, Fusarium nigricans, Fusarium spp. ... subglutinans, Gaeumannomyces graminis, Helminthosporium spp., Microdochium nivale, Phoma spp., Pyrenophora graminea, Pyricularia oryzae, Rhizoctonia solani, Rhizoctonia cerealis, Sclerotinia spp., Zymoseptoria spp., Sphacelotheca reilliana, Tilletia spp., Typhula incarnata It may furthermore be particularly effective against seed-borne and soil-borne diseases such as Urocystis incarnata, Urocystis occulta, Ustilago species or Verticillium species, and is effective against a wide range of crops, especially cereals such as wheat, barley, rye or oats; maize; rice; cotton; soybeans; turf; sugar beet; oilseed rape; potatoes;It may be effective against pathogens of peas, lentils, or chickpeas; and sunflowers.

[0054] The compositions according to the invention are effective against Botrytis cinerea, Colletotrichum musae, Curvularia lunata, Fusarium semitecum, Geotrichum candidum, Monilinia fructicola, Monilinia fructigena, Monilinia laxa, Mucor piriformis, Penicillium italicum, Penicillium solitum, Penicillium digitatum or Penicillium expansum. expansum), especially against fruit pathogens such as pome fruit, e.g., apple and pear, stone fruit, e.g., peaches and plums, citrus fruits, melon, papaya, kiwi, mango, berries, e.g., strawberry, avocado, pomegranate and banana, and tree nuts.

[0055] The compositions according to the invention may be particularly useful for controlling the following diseases on the following crops: Alternaria species in fruits and vegetables and potatoes; Botrytis cinerea in strawberries, tomatoes, sunflowers, cereals, vegetables and grapes; Rhizoctonia solani in potatoes and vegetables, Uncinula necator in grapes, Cladosporium cucumerinum, Didymella bryoniae, Sphaerotheca fuliginea and Glomerella lagenarium in cucurbits and solanaceous crops, Leveillula taurica in cucurbits and solanaceous crops. taurica, Fusarium spp., Zympseptoria tritici etc. in cereals, Septoria spp., Septoria glycines etc. in cereals, Septoria spp., in oil crops, Mycosphaerella arachidicola etc. in peanuts, Cercospora spp. in tomatoes, beans, peanuts and oil crops or Cercospora sojinae and Cercospora kikuchii in soybeans.

[0056] However, in addition to the actual synergistic action with regard to fungicidal activity, the compositions according to the invention may also have further surprising advantageous properties. Examples of such advantageous properties that may be mentioned are more advantageous decomposition; improved toxicological and / or ecotoxicological behavior; or improved properties of useful plants, including: emergence, crop yield, more developed root system, increased tillers, increased plant height, increased leaf blades, less dead basal leaves, stronger tillers, greener leaf color, reduced fertilizer requirement, reduced seed requirement, more productive tillers, earlier flowering, earlier grain maturation, less plant bursting (lodging), increased shoot growth, improved plant vigor and earlier germination.

[0057] Some of the compositions according to the invention have systemic action and can be used as foliar, soil and seed treatment fungicides.

[0058] The compositions according to the invention make it possible to inhibit or destroy phytopathogenic microorganisms present on the plants or plant parts (fruits, flowers, leaves, stems, tubers, roots) of various useful plants, while also protecting subsequently growing plant parts from attack by phytopathogenic microorganisms.

[0059] The compositions according to the invention can be applied to phytopathogenic microorganisms, useful plants, their locus, their propagation material, stored goods or industrial products threatened by microbial attack.

[0060] The compositions according to the invention can be applied before or after infection by microorganisms of useful plants, their propagation material, stored goods or industrial products.

[0061] The amount of the composition according to the invention to be applied depends on various factors, such as the compound used; the object of treatment, e.g., plants, soil or seeds; the type of treatment, e.g., spraying, dusting or seed dressing; the purpose of the treatment, e.g., preventive or curative; the type of fungus to be controlled or the duration of application.

[0062] When applied to useful plants, component (A) is typically applied at a rate of 5 to 2000 g ai / ha, especially 10 to 1000 g ai / ha, for example 50, 75, 100 or 200 g ai / ha, typically together with component (B) at 1 to 5000 g ai / ha, especially 2 to 2000 g ai / ha, for example 100, 250, 500, 800, 1000, 1500 g ai / ha.

[0063] In agricultural practice, the rate of application of the compositions according to the invention depends on the type of effect desired and typically ranges from 20 to 4000 g of total composition per hectare.

[0064] When the compositions according to the invention are applied for seed treatment, a rate of 0.001 to 50 g of the compound of component (A) per kg of seed, preferably 0.01 to 10 g per kg of seed, and 0.001 to 50 g of the compound of component (B) per kg of seed, preferably 0.01 to 10 g per kg of seed, is generally sufficient.

[0065] The compositions of the present invention may be in any conventional form, such as twin packs, dry seed treatment powders (DS), emulsifiable concentrates (ES), flowable seed treatment concentrates (FS), liquid seed treatment solutions (LS), wettable powders (WS), suspension capsules (CF), gels (GF), emulsifiable concentrates (EC), suspension concentrates (SC), suspoemulsions (SE), suspension capsules (CS), water dispersible granules (WG), emulsifiable granules (E), etc. They may be used in the form of emulsions (G), water-in-oil emulsions (EO), oil-in-water emulsions (EW), microemulsions (ME), dispersions in oil (OD), oil-miscible flowables (OF), oil-miscible liquids (OL), soluble concentrates (SL), suspension concentrates for ultra-low volume application (SU), liquid concentrates for ultra-low volume application (UL), technical concentrates (TK), dispersible concentrates (DC), wettable powders (WP) or any technically feasible formulation, in combination with agriculturally acceptable adjuvants.

[0066] Such compositions can be prepared in a conventional manner, for example, by mixing the active ingredient with at least one suitable inert formulation auxiliary (e.g., diluents, solvents, fillers, and other formulation components such as surfactants, biocides, antifreeze agents, adhesives, thickeners, and optionally, compounds providing auxiliary effects). Alternatively, if sustained effectiveness is desired, conventional sustained-release formulations can be utilized. In particular, formulations to be applied in spray form, such as wettable concentrates (e.g., EC, SC, DC, OD, SE, EW, EO, etc.), wettable powders, and granules, may contain surfactants such as wetting agents and dispersants, as well as other compounds providing auxiliary effects, such as condensation products of formaldehyde and naphthalenesulfonate, alkylarylsulfonates, ligninsulfonates, fatty alkyl sulfates, and ethoxylated alkylphenols and ethoxylated fatty alcohols.

[0067] The composition according to the invention may further comprise a pesticide, such as a fungicide, insecticide or herbicide.

[0068] The seed dressing formulation is applied to seeds in a manner known per se, using the composition according to the present invention and a suitable diluent in the form of a seed dressing formulation, for example, as an aqueous suspension or in the form of a dry powder that has good adhesion to seeds.Such seed dressing formulations are known in the art.The seed dressing formulation may also contain a single active ingredient or a combination of active ingredients in encapsulated form, for example, as sustained-release capsules or microcapsules.

[0069] Typically, the formulation contains 0.01 to 90% by weight of active agent, 0 to 20% of an agriculturally acceptable surfactant, and 10 to 99.99% of solid or liquid formulation inactive substances and adjuvants, where the active agent consists of at least the compound of component (A) and the compound of component (B), and optionally other active agents, particularly fungicides or preservatives. Concentrated compositions generally contain about 2 to 80% by weight, preferably about 5 to 70% by weight, of the active agent. Application formulations may contain, for example, 0.01 to 20% by weight, preferably 0.01 to 5% by weight, of the active agent. Commercially available products will preferably be formulated as concentrates, but end users will usually utilize diluted formulations.

[0070] Further characteristics of compositions containing a compound of formula (I), their methods of application to plants, and their use rates are as described for compositions containing a compound of formula (I) and at least one of the above-mentioned components (B). Their application can be before or after fungal infection of the plant or its parts. Treatment is preferably carried out before infection. When a compound of formula (I) is used per se, the application rate in the method according to the invention is as described above, e.g., 5 to 2000 g ai / ha, in particular 10 to 1000 g ai / ha, e.g., 50, 75, 100, or 200 g ai / ha, is typical. The compound of formula (I) can be applied to plants once or more than once during the growing season. For use in the method according to the invention, the compound of formula (I) can be converted into the above-mentioned conventional formulations, such as solutions, emulsifiable concentrates, suspensions, dusts, powders, pastes, and granules. The use form depends on the specific intended purpose. In each case, it should ensure a fine and uniform distribution of the compound of formula (I).

[0071] As used herein, the term "plants" includes fruit and vegetable seedlings, shrubs and crops.

[0072] The following examples are useful for illustrating the present invention, and "active ingredient" refers to a mixture of component (A) and component (B) in a specific mixing ratio. The same formulation can be used for a composition containing only the compound of formula (I) as the active ingredient, as shown in the table below. [Example]

[0073] Formulation Examples

[0074] [Table 1]

[0075] The active ingredient is thoroughly mixed with the other formulation ingredients and the mixture is thoroughly ground in a suitable grinder to give a wettable powder which, when diluted with water, gives a suspension of the desired concentration.

[0076] [Table 2]

[0077] The active ingredient is thoroughly mixed with the other formulation ingredients and the mixture is thoroughly ground in a suitable grinder to give a powder which can be used directly as a seed treatment.

[0078] Table 3 emulsifiable concentrate Active ingredients (A):B) = 1:6) 10% Octylphenol polyethylene glycol ether 3% (4-5 moles of ethylene oxide) Calcium dodecylbenzenesulfonate 3% Castor oil polyethylene glycol ether (35 moles of ethylene oxide) 4% Cyclohexanone 30% Xylene mixture 50%

[0079] Emulsions of any required dilution that can be used for plant protection can be obtained from this concentrate by dilution with water.

[0080] [Table 3]

[0081] Ready-to-use dusts can be obtained by mixing the active ingredient with a carrier and grinding the mixture in a suitable grinder. Such powders can also be used as dry seed dressings.

[0082] Table 5 Extruded Granules %w / w Active ingredients (A):B) = 2:1) 15% Sodium Lignosulfonate 2% Sodium alkylnaphthalene sulfonate 1% Kaolin 82%

[0083] The active ingredient is mixed and ground with the other formulation ingredients, the mixture is moistened with water, the mixture is extruded and then dried in a current of air.

[0084] Suspension concentrate Table 6 Active ingredients (A):B) = 1:8) 40% Propylene glycol 10% Nonylphenol polyethylene glycol ether (15 moles of ethylene oxide) 6% Sodium Lignosulfonate 10% Carboxymethylcellulose 1% Silicone oil (in the form of a 75% emulsion in water) 1% water 32%

[0085] The finely divided active ingredient, when thoroughly mixed with the other formulation ingredients, gives a suspension concentrate which can be diluted with water in the desired proportions and used to treat living plants and plant propagation material to protect against microbial infestation by spraying, pouring or dipping.

[0086] Flowable concentrate for seed treatment Table 7 Active ingredients (A):B) = 1:8) 40% Propylene glycol 5% Copolymer butanol PO / EO 2% Tristyrenephenol ethoxylate (with 10-20 moles of EO) 2% 1,2-benzisothiazolin-3-one 0.5% Monoazo pigment calcium salt 5% Silicone oil (in the form of a 75% emulsion in water) 0.2% Water 45.3%

[0087] The finely divided active ingredient, when thoroughly mixed with the other formulation ingredients, gives a suspension concentrate which can be further diluted in water for application to seeds, and such dilutions can be used to treat propagation material to protect against microbial attack by spraying, pouring or dipping.

[0088] Thus, a further aspect of the invention is a method for controlling leaf spot diseases on plants, which method comprises applying to the plant, its locus or its propagation material a composition comprising a compound of formula (I).

[0089] Preferred are methods in which plant pathogens attack plants, causing diseases such as leaf spot, powdery mildew and blight.

[0090] Preferred is a method which comprises applying a composition comprising a compound of formula (I) to the plant or its locus, preferably the plant.

[0091] Further preferred is a method comprising applying a composition comprising a compound of formula (I) to the propagation material of a plant, and furthermore the present invention also relates to the use of a composition according to the invention for controlling leaf spot diseases on plants.

[0092] The method according to the invention also allows good control of other harmful fungi which often occur in plants, in particular when the compounds of formula (I) are used in combination with at least one of the above-mentioned compounds (B).

[0093] A method for controlling diseases on oil crops and cereals, particularly diseases caused by leaf spot diseases, is preferred, and this method comprises 1 and R 2are, independently of each other, fluoro, chloro or trifluoromethyl, and R 3 is methyl or ethyl, A is N, and X is C(=O) or O. [ka] The method comprises applying a composition containing the compound of formula (I) to the useful plant, its locus or its propagation material.

[0094] 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 100:1 to 1:100, more preferably 20:1 to 1:50, even more preferably 12:1 to 1:25, even more preferably 10:1 to 1:10, still more preferably 5:1 to 1:15, and most preferably 2:1 to 1:5.

[0095] It has been surprisingly found that certain weight ratios of component (A) and component (B) can result in synergistic activity. Accordingly, a further aspect of the present invention is a composition in which component (A) and component (B) are present in the composition in amounts that result in a synergistic effect. This synergistic activity is evident from the fact that the fungicidal activity of a composition comprising component (A) and component (B) is higher than the sum of the fungicidal activities of component (A) and component (B).

[0096] This synergistic activity expands the spectrum of action of components (A) and (B) in two ways. First, the application rate of components (A) and (B) can be reduced while the activity remains similarly good, meaning that the active ingredient mixture still achieves a high degree of plant pathogen control even when the two individual components become completely ineffective at such low application rate ranges. Second, there is a significant expansion of the spectrum of plant pathogens that can be controlled.

[0097] A synergistic effect exists whenever the effect of the active ingredient combination is higher than the sum of the effects of the individual ingredients. The expected effect E of a given active ingredient combination can be calculated according to the so-called Colby formula as follows (COLBY, SR "Calculating synergistic and antagonistic responses of herbicide combinations". Weeds, Vol. 15, pages 20-22; 1967): ppm = milligrams of active ingredient (=ai) per liter of spray mixture X = % effect of active ingredient A) using p ppm of active ingredient Y = % effect of active ingredient B) using q ppm of active ingredient.

[0098] According to Colby, the expected (additive) effect of active ingredients A) + B) using p+q ppm of active ingredients is:

number

[0099] If the actual observed effect (O) is higher than the expected effect (E), the effect of the combination is superadditive, i.e., synergistic. Mathematically speaking, synergy corresponds to a positive value of the difference (OE). In the case of purely additive complementary activities (expected activity), the difference (OE) is zero. A negative value of the difference (OE) represents a decrease in activity compared to the expected activity.

[0100] Biological Examples Corynespora cassiicola (target spot of soybean, target leaf spot of tomato): Fungal conidia released from cryogenic storage were mixed directly into nutrient broth (PDB potato dextrose broth). DMSO solutions of test compounds were placed into microtiter plates (96-well format) followed by the addition of the nutrient broth containing the fungal spores. Test plates were incubated at 24°C, and growth inhibition was determined photometrically at 620 nm after 3-4 days. The rates and results are shown in the table below.

[0101] [Table 4]

[0102] [Table 5]

[0103] Mycosphaerella arachidis syn. Cercospora arachidicola (Peanut brown leaf spot): Fungal conidia released from cryogenic storage were mixed directly into nutrient broth (PDB potato dextrose broth). DMSO solutions of test compounds were placed in microtiter plates (96-well format) followed by the addition of the nutrient broth containing the fungal spores.

[0104] Test plates were incubated at 24°C and growth inhibition was determined photometrically at 620 nm after 5-6 days.

[0105] [Table 6]

[0106] Septoria tritici (leaf blotch): Fungal conidia released from cryogenic storage were mixed directly into nutrient broth (PDB potato dextrose broth). DMSO solutions of test compounds were placed into microtiter plates (96-well format) followed by the addition of the nutrient broth containing the fungal spores. Test plates were incubated at 24°C, and growth inhibition was determined photometrically after 72 hours.

[0107] [Table 7]

[0108] [Table 8]

[0109] Septoria glycines (brown spots): Fungal conidia released from cryogenic storage were mixed directly into nutrient broth (PDB potato dextrose broth). DMSO solutions of test compounds were placed into microtiter plates (96-well format) followed by the addition of the nutrient broth containing the fungal spores. Test plates were incubated at 24°C, and growth inhibition was determined photometrically after 72 hours.

[0110] [Table 9]

[0111] [Table 10]

[0112] [Table 11]

[0113] [Table 12]

[0114] Table 13

[0115] Table 14

[0116] Table 15

[0117] Table 16

[0118] Table 17

[0119] Table 18

[0120] Table 19 Another aspect of the present invention may be as follows. [1] A composition suitable for controlling diseases caused by plant pathogens, (A) Formula I [C1] JPEG0007783823000024.jpg59124 (In the formula, R 1 and R 2 are each independently a halogen, cyano or C 1 ~C 3 haloalkyl, and R 3 is hydrogen, C 1 ~C 3 Alkyl, C 1 ~C 3 Alkenyl or C 1 ~C 3 alkynyl, A is CH or N, and X is CH 2 , C(=O), O or S) or a pesticidally acceptable salt or N-oxide thereof, and (B) at least one compound selected from the group consisting of benzothiostrobin, cyclobutrifluram, florylpicoxamide, fluveneteram, fluopimomide, fluoxapiprolin, ipflufenoquin, mandestrobin, methyltetraprole, pyridaclomethyl, pyriophenone, pyrisoxazole, 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide, N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamide, amidine, N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, (Z,2E)-5-[1-(4-chlorophenyl)pyrazole-3- yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, 1-(5,6-dimethyl-3-pyridyl)-4,4-difluoro-3,3-dimethyl-isoquinoline, 1-[6-(difluoromethyl)-5-methyl-3-pyridyl]-4,4-difluoro-3,3-dimethyl-isoquinoline, 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)- N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide, [1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, [1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, 2,at least one compound selected from 2-difluoro-N-[6-[[1-(1-methyltetrazol-5-yl)benzimidazol-2-yl]oxymethyl]-2-pyridyl]-2-phenoxy-acetamide, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile, 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile, or a combination thereof, A composition comprising: [2] In compound (A), R 1 and R 2 are, independently of each other, fluoro, chloro or trifluoromethyl; R 3 is methyl or ethyl, A is N, and X is C(=O) or O, or an agriculturally acceptable salt or N-oxide thereof according to [1] above. [3] In component (A), R 1 and R 2 are each independently chloro or trifluoromethyl. [4] In component (A), R 3 is methyl or ethyl. [5] The composition according to any one of the above [1] to [4], wherein in the component (A), A is N. [6] The composition according to any one of the above [1] to [5], wherein in component (A), X is C(=O) or O. [7] Component (A) is methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoate or ethyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoate, and component (B) is flurylpicoxamide, fluveneteram, fluopimomide, fluoxapiprolin, ipflufenoquin, Mandestrobin, methyltetraprole, pyriophenone, pyrisoxazole, 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide, N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propanol Pan-2-ol, (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, 1-(5,6-dimethyl-3-pyridyl)-4,4-difluoro-3,3-dimethyl-isoquinoline, 1-[6-(difluoromethyl)-5-methyl-3-pyridyl]-4,4-difluoro-3,3-dimethyl-isoquinoline, 2,2-difluoro-N-methyl-2-[4-[5-( The composition according to [1], wherein the fungicide is selected from the group consisting of N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide, [1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, and combinations thereof. [8] Component (A) is methyl 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoate, and component (B) is flurylpicoxamide, fluveneteram, fluopimomide, fluoxapiprolin, ipflufenoquin, mandestrobin, methyltetraprole, pyriophenone, pyrisoxazole, 2-(difluoro Methyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide, N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, (Z,2E)-5-[1-(2,4-dichloro Phenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, 1-(5,6-dimethyl-3-pyridyl)-4,4-difluoro-3,3-dimethyl-isoquinoline, 1-[6-(difluoromethyl)-5-methyl-3-pyridyl]-4,4-difluoro-3,3-dimethyl-isoquinoline, 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2, The composition according to [1], wherein the fungicide is selected from the group consisting of N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide, [1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, and combinations thereof. [9] The composition according to any one of the above [1] to [8], wherein the weight ratio of (A) to (B) is in the range of 2000:1 to 1:1000.

[10] The composition according to [9], wherein the weight ratio of (A) to (B) is in the range of 100:1 to 1:100, preferably 20:1 to 1:40, more preferably 12:1 to 1:25, even more preferably 5:1 to 1:15, and still more preferably 2:1 to 1:5.

[11] The composition according to any one of [1] to

[10] above, which comprises at least one or more additional insecticidal active agents, acaricidal active agents, nematicidal active agents and / or fungicidal active agents.

[12] The additional active agent is selected from the group consisting of flurylpicoxamide, fluveneteram, fluopimomide, fluoxapiprolin, ipflufenoquin, mandestrobin, methyltetraprole, pyriophenone, pyrisoxazole, 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide, N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N -ethyl-N-methyl-formamidine, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, 1-(5,6-dimethyl-3-pyridyl)-4,4-difluorophenyl 12. The composition according to claim 11, further comprising one or more insecticides selected from at least one compound selected from the group consisting of N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide, [1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, wherein the at least one or more further insecticides are selected from the group defined herein above, but are different from component (B).

[13] The composition according to any one of [1] to

[12] above, further comprising an agriculturally acceptable carrier, and optionally a surfactant and / or formulation adjuvant.

[14] A method for controlling diseases caused by plant pathogens on useful plants or their propagation materials, comprising applying the composition described in [1] to the useful plants, their locus, or their propagation materials.

[15] The method according to

[14] , wherein the composition components (A) and (B) are applied simultaneously, intermittently, or sequentially.

[16] Coated plant propagation material, wherein the coating of the plant propagation material comprises a composition according to any one of [1] to

[13] .

Claims

1. 1. A composition suitable for controlling diseases caused by plant pathogens, comprising: (A) Formula I 【Chemistry 1】 (In the formula, R 1 and R 2 are each independently chloro or trifluoromethyl, R 3 is methyl or ethyl, A is N, and X is O. or an agriculturally acceptable salt or N-oxide thereof, and (B) at least one compound selected from benzothiostrobin, cyclobutrifluram, florylpicoxamide, fluopimomide, ipflufenoquin, mandestrobin, methyltetraprole, pyriophenone, pyrisoxazole, or a combination thereof; 2. A composition comprising: 2 is Cl, and R 3 is CH 3 and excluding compositions in which component (B) is methyltetraprole.

2. 2. The composition of claim 1, wherein component (A) is methyl 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoate.

3. 3. The composition according to claim 1, wherein the weight ratio of (A) to (B) is in the range of 2000:1 to 1:1000.

4. 4. The composition of claim 3, wherein the weight ratio of (A) to (B) ranges from 100:1 to 1:

100.

5. 4. The composition of claim 3, wherein the weight ratio of (A) to (B) ranges from 20:1 to 1:

40.

6. 4. The composition of claim 3, wherein the weight ratio of (A) to (B) ranges from 12:1 to 1:

25.

7. 4. The composition of claim 3, wherein the weight ratio of (A) to (B) ranges from 5:1 to 1:

15.

8. 4. The composition of claim 3, wherein the weight ratio of (A) to (B) ranges from 2:1 to 1:

5.

9. The composition according to any one of claims 1 to 8, comprising at least one further insecticidal, acaricidal, nematicidal and / or fungicidal active agent.

10. The further active agent may be flurylpicoxamide, fluveneteram, fluopimomide, fluoxapiprolin, ipflufenoquin, mandestrobin, methyltetraprole, pyriophenone, pyrisoxazole, 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide, N'-(2-chloro-5-methyl-4-phenoxy- phenyl)-N-ethyl-N-methyl-formamidine, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, 1-(5,6-dimethyl 10. The composition of claim 9, comprising one or more insecticides selected from at least one compound selected from N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide, [1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, wherein said additional active agent is different from component (B).

11. The composition of any one of claims 1 to 10, further comprising an agriculturally acceptable carrier and, optionally, a surfactant and / or formulation adjuvant.

12. A method for controlling diseases caused by plant pathogens on useful plants or their propagation material, comprising applying to said useful plants, their locus or their propagation material a composition according to claim 1.

13. 13. The method of claim 12, wherein components (A) and (B) are applied simultaneously, intermittently, or sequentially.

14. A coated plant propagation material, wherein the coating of the plant propagation material comprises a composition according to any one of claims 1 to 11.

Images