fungicidal composition

Abstract

A composition suitable for controlling diseases caused by plant pathogens, comprising (A) a compound of formula I, wherein R 1 and R 2 are independently halogen, cyano or C1-C3 haloalkyl, 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) at least one compound selected from compounds known for their fungicidal activity; and a method for controlling diseases on useful plants, especially leaf spot on cereals. #imgabs0#

Description

[0001] The present invention relates to novel fungicidal compositions which are suitable for controlling diseases caused by plant pathogens, especially phytopathogenic fungi, and to a method for controlling diseases on useful plants, especially fruit and vegetables.

[0002] WO 2019 / 093522 discloses that certain 2-hydroxypropionic acid ester derivatives and mixtures containing them exhibit biological activity against phytopathogenic fungi. On the other hand, various fungicidal compounds from different chemical classes are well known as botanical fungicides for use in various cultivated plant crops. However, crop tolerance and activity against phytopathogenic fungi do not always meet the requirements of agricultural practice in many areas and contexts. In particular, pathogens that cause leaf spot diseases, such as Mycosphaerella arachidis (the causative agent of peanut leaf spot), Corynespora casiicola (the causative agent of target spot disease of tomatoes and soybeans), Septoria spp. (causing leaf spot diseases on a wide range of important crops, such as wheat and soybeans), but also mildew diseases, such as Uncinula necator (the causative agent of powdery mildew of grapes) and fungal blights, such as Botrytis cinerea (the causative agent of gray mold of different crop plants), are becoming an increasingly important problem in crop production, causing considerable yield losses. Many conventional fungicides are unsuitable for controlling leaf spot, powdery mildew and gray mold, or their action against Septoria species, such as Zymoseptoria tritici, Septoria glycines, Powdery mildew of grapes and Botrytis cinerea, is unsatisfactory.

[0003] In view of the need for improved crop tolerance and / or improved activity against plant pathogenic fungi (such as leaf spot fungi, powdery mildew fungi and mold fungi) in the above-mentioned agricultural practice, the present invention provides a novel composition suitable for controlling diseases caused by plant pathogens, which composition comprises:

[0004] (A) Compounds having formula I

[0005]

[0006] where R 1 and R 2 are independently halogen, cyano or C1-C3 haloalkyl, R 3is 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

[0007] (B) at least one compound selected from the group consisting of benzathiostrobin, cyclobutrifluram, florylpioxamid, fluoxapiprolin, ipflufenoquin, mandestrobin, metyltetraprole, pyridachlometyl, benzathiostrobin, pyraclostrobin, 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-pyridine-3-carboxamide, 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)pyrazol-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 imino-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]thiobenzamide, (2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propanoic acid [1-methyl-2-(o-tolyl)propyl] ] ester, (2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propionic acid [1-methyl-2-(o-tolyl)propyl] ester, 2,2-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.

[0008] The presence of one or more asymmetric carbon atoms in compounds of formula I means that these compounds can exist in the form of optical isomers (i.e., enantiomers or diastereomers). As a result of restricted rotation around a single bond, atropisomers may also exist. The present invention includes all those possible isomeric forms of 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 compounds of formula I, and also includes racemic compounds, i.e., mixtures of at least two enantiomers in a ratio of substantially 50:50.

[0009] In each case, the compounds of formula I according to the invention are in free form, in an oxidized form (such as an N-oxide) or in the form of a salt (for example an agronomically usable salt).

[0010] N-oxides are oxidized forms of tertiary amines or oxidized forms of nitrogen-containing heteroaromatic compounds. They are described, for example, by A. Albini and S. Pietra in 1991 in the book "Heterocyclic N-oxides", published by CRC Press, Boca Raton.

[0011] Preferred compositions are those comprising:

[0012] (A) Compounds having formula I

[0013]

[0014] where R 1 and R 2 are independently fluoro, chloro or trifluoromethyl, R 3 is methyl or ethyl, A is N and X is C(═O) or O; and

[0015] (B) at least one compound selected from the group consisting of pyrithione, flufenoxamide, fluoxapiprolin, ipflufenoquin, mandestrobin, metyltetraprole, pyridoxazole, pyraclostrobin, 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)-1-yl]-1-propan-2-ol, 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]thiobenzamide, (2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propionic acid [1-methyl-2-(o-tolyl)propyl] ester.

[0016] It has been found that the use of component (B) in combination with component (A) unexpectedly and substantially enhances the effectiveness of the latter against fungi, and vice versa. Furthermore, the method of the present invention, when used independently and alone, is effective against a wider spectrum of fungi than those that can be combated with the active ingredients of the method.

[0017] Another aspect of the present invention is to control the method for the disease caused by plant pathogens on useful plants or on its propagation material, and the method comprises applying to these useful plants, its place or its propagation material according to the composition of the present invention.Preferably the following method, it comprises applying to these useful plants or its place according to the composition of the present invention, more preferably applying to these useful plants.Preferably the following method, it comprises applying to the propagation material of these useful plants according to the composition of the present invention.The present invention encompasses all stereoisomers and mixtures thereof in any ratio.

[0018] Preferred embodiments of the present invention are represented by those compositions comprising as component A) a compound having formula (I) wherein A is N and X is O, and most preferably wherein R 1 is chlorine, R 2 is chlorine, R 3 is methyl, A is N and X is O; or R1 is chlorine, R 2 is chlorine, R 3 is ethyl, A is N and X is O; or R 1 is chlorine, R 2 is trifluoromethyl, R 3 is methyl, A is N and X is O. The preferred compounds of formula (I) are:

[0019] 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).

[0020] Further preferred embodiments of the present invention are represented by those compositions which comprise as component B) a fungicide selected from the group consisting of pyridamole, flufenoxamide, fluoxaporthamide, fluoxapiprolin, ipflufenoquin, mandestrobin, metyltetraprole, pyraclostrobin, pyraclostrobin, 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]thiobenzamide, (2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propionic acid [1-methyl-2-(o-tolyl)propyl] ester.

[0021] Particularly preferred compositions according to the invention comprise a methyl ester selected from the group consisting of 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoate (compound A-1.1), 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoate (compound A-1.2), and 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoate. as component (A) and a compound selected from the group consisting of pyridamole, fluphenazine, fluoxapiprolin, ipflufenoquin, mandestrobin, metyltetraprole, pyraclostrobin, pyraclostrobin, 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide, N'-(2-chloro-1,1-indane-3-yl)pyridine-3-carboxamide, N'-(2-chloro-1,1-indane-3-yl)pyridine-4 ...4-carboxamide, N'-(2-chloro-1,1-indane-3-yl)pyridine-3-carboxamide, N'-(2-chloro-1,1-indane-3-yl)pyridine-4-carboxamide, N'-(2-chloro-1,1-indane-3-yl)pyridine-4-carboxamide, N'-(2-chloro-1,1-indane-3-yl)pyridine-4-carboxamide, N'-(2-chloro-1,1-indane-3 -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]thiobenzamide, (2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propionic acid [1-methyl-2-(o-tolyl)propyl] ester.

[0022] Compounds of formula (I) can be prepared in a similar manner as outlined in WO 2019 / 093522 by chemical reactions known in the art.

[0023] Component (B) is known. Most of the components (B) are referred to above by the so-called "ISO common name" or, in individual cases, another "common name" or a trademark.

[0024] The following preferred components (B) are included in the UK Crop Production Council's online pesticide handbook ("E-Pesticide Handbook") and in Alan Wood's compilation of common names of pesticides: benzathiastrobin, cyclobutrifluram, pyridamole, fluphenazine, fluoxapyramide, fluoxapiprolin, ipflufenoquin, mandestrobin, metyltetraprole, pyridachlometyl, pyraclostrobin, pyraclostrobin.

[0025] 2-(Difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide is disclosed in WO2019 / 224175.

[0026] N′-(2-Chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine is disclosed in WO 2017 / 005710.

[0027] N'-[2-Chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine is disclosed in WO 2016 / 202742.

[0028] 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol is disclosed in WO 2018 / 145921.

[0029] 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol is disclosed in WO 2018 / 145921.

[0030] (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide is disclosed in WO 2013 / 092224.

[0031] (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.

[0032] 1-(5,6-Dimethyl-3-pyridyl)-4,4-difluoro-3,3-dimethyl-isoquinoline is disclosed in WO 2017 / 016915.

[0033] 1-[6-(Difluoromethyl)-5-methyl-3-pyridyl]-4,4-difluoro-3,3-dimethyl-isoquinoline is disclosed in WO2017 / 016915.

[0034] 2,2-Difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide is disclosed in WO 2017 / 076742.

[0035] N-Methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide is disclosed in WO 2017 / 211649.

[0036] (2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propionic acid [1-methyl-2-(o-tolyl)propyl] ester is disclosed in WO 2019 / 173665.

[0037] (2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propionic acid [1-methyl-2-(o-tolyl)propyl] ester is disclosed in WO 2019 / 173665.

[0038] 2,2-Difluoro-N-[6-[[1-(1-methyltetrazol-5-yl)benzimidazol-2-yl]oxymethyl]-2-pyridinyl]-2-phenoxy-acetamide is disclosed in WO 2017 / 178819.

[0039] N-Methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide is disclosed in WO 2017 / 174158.

[0040] 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile is disclosed in WO 2016 / 156290.

[0041] 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile is disclosed in WO2016 / 156290.

[0042] Examples of particularly suitable compounds as component (B) are compounds selected from the following group P: pyridamole, flufenoxamide, fluoxaporthamide, fluoxapiprolin, ipflufenoquin, mandestrobin, metyltetraprole, pyridamole, pyraclostrobin, 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]thiobenzamide, (2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propionic acid [1-methyl-2-(o-tolyl)propyl] ester.

[0043] Throughout this document, the expression "composition" represents various mixtures or combinations of components (A) and (B), for example in a single "ready-to-use" form, in a combined spray mixture (which mixture consists of separate formulations of the individual active ingredient components) (such as a "tank mix"), and in combination with the individual active ingredients when applied in a sequential manner (i.e. one after the other over a reasonably short period of time, such as a few hours or days). For the practice of the present invention, the order in which components (A) and (B) are applied is not important.

[0044] Further examples of compositions according to the invention comprising three active ingredients are defined as in Examples E1, E2 and E3:

[0045] Preferred embodiment E1:

[0046] The term "TX1" means herein: "Compound A-1.1 + a compound selected from group P". Preferred examples include the following compositions: benzathiostrobin + TX1, cyclobutrifluram + TX1, pyridosporamide + TX1, fluphenazine + TX1, fluoxaporin + TX1, fluoxapiprolin + TX1, ipflufenoquin + TX1, mandestrobin + TX1, metyltetraprole + TX1, pyridachlometyl + TX1, benzathiostrobin + TX1, pyrazoconazole + TX1, 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-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-methoxyimino N,3-dimethyl-pent-3-enamide + 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)-1,2,4-oxadiazol-3-yl]phenyl]acetamide + TX1, N-methyl-4-[5 -(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiobenzamide + TX1, (2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propionic acid [1-methyl-2-(o-tolyl)propyl] ester + TX1, (2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propionic acid [1-methyl-2-(o-tolyl)propyl] ester + 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-hydroxy-propyl]imidazole-4-carbonitrile+TX1, 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile+TX1.

[0047] Preferred embodiment E2:

[0048] The term "TX2" means: "Compound A-1.2 + a compound selected from group P".

[0049] Preferred examples include the following compositions: benzathiostrobin + TX2, cyclobutrifluram + TX2, pyridoxamido + TX2, fluoxapiprolin + TX2, ipflufenoquin + TX2, mandestrobin + TX2, metyltetraprole + TX2, pyridachlometyl + TX2, benzathiostrobin + TX2, pyrazoconazole + 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-methoxyimino N,3-dimethyl-pent-3-enamide + 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)-1,2,4-oxadiazol-3-yl]phenyl]acetamide + TX2, N-methyl-4-[5 -(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiobenzamide + TX2, (2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propionic acid [1-methyl-2-(o-tolyl)propyl] ester + TX2, (2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propionic acid [1-methyl-2-(o-tolyl)propyl] ester + 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-hydroxy-propyl]imidazole-4-carbonitrile+TX2, 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile+TX2.

[0050] Preferred embodiment E3:

[0051] The term "TX3" means: "Compound A-1.3 + a compound selected from group P".

[0052] Preferred examples include the following compositions: benzathiostrobin + TX3, cyclobutrifluram + TX3, pyridoxamido + TX3, fluphenazine + TX3, fluoxapiprolin + TX3, ipflufenoquin + TX3, mandestrobin + TX3, metyltetraprole + TX3, pyridachlometyl + TX3, benzathiostrobin + TX3, pyrazoconazole + TX3, 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-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-methoxyimino N,3-dimethyl-pent-3-enamide + TX3, (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide + TX3, 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)-1,2,4-oxadiazol-3-yl]phenyl]acetamide + TX3, N-methyl-4-[5 -(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiobenzamide + TX3, (2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propionic acid [1-methyl-2-(o-tolyl)propyl] ester + TX3, (2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propionic acid [1-methyl-2-(o-tolyl)propyl] ester + 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-hydroxy-propyl]imidazole-4-carbonitrile+TX3, 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile+TX3.

[0053] Examples E1, E2, and E3 define compositions according to the present invention, comprising three active ingredients. In these examples, the compound selected from Group P must be different from the other described compounds. For example, the composition "benthiostrobin + TX1" refers to a composition comprising benzthiostrobin, compound A-1.1, and a compound selected from Group P as active ingredients. In these compositions, the compound selected from Group P is different from benzthiostrobin.

[0054] The following compositions are preferred:

[0055] 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 benzathiastrobin.

[0056] The compositions according to the invention are effective against unwanted microorganisms, such as microorganisms causing phytopathogenic diseases, in particular against phytopathogenic fungi and bacteria.

[0057] The compositions according to the invention are particularly effective against phytopathogenic fungi belonging to the following classes: Ascomycetes (e.g. Venturia, Pseudomonas, Erysiphe, Cochliobolus, Mycosphaeria, Uncinula); Basidiomycetes (e.g. Hemileia, Rhizoctonia, Puccinia, Puccinia, Ustilago, Tilletia); Imperfect Fungi (also known as Deuteromycetes, e.g. Botrytis, Helminthosporium, Rhynchosporium, Fusarium, Zymoseptoria, Cercospora, Alternaria, Pyrospora and Pseudocercosporium); Oomycetes (e.g. Phytophthora, Downy Mildew, Pseudocercospora, Albugo, Discoideum, Pythium, Pseudocercoideum, Monoparagus).

[0058] According to the present invention, "useful plants" typically include the following plant species: grapevines; cereals, such as wheat, barley, rye or oats; beets, such as sugar beets or fodder beets; fruits, such as pome, stone or soft fruits, for example apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries or blackberries; leguminous plants, such as beans, lentils, peas or soybeans; oil crops, such as rapeseed, mustard, poppy, olives, sunflowers, coconuts, castor oil plants, cocoa beans or peanuts; cucumbers, such as zucchini, Gourds, cucumbers, or cantaloupes; fiber plants such as cotton, flax, hemp, or jute; citrus fruits such as oranges, lemons, grapefruits, or mandarins; vegetables such as spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, gourds, or peppers; Lauraceae plants such as avocado, cinnamon, or camphor; corn; tobacco; nuts; coffee; sugarcane; tea; vines; hops; durian; bananas; natural rubber plants; turf or ornamental plants such as flowers, shrubs, broadleaf trees, or evergreens, such as pines and cypresses. This list is not intended to be limiting.

[0059] The term "useful plants" is to be understood as including useful plants which have been rendered tolerant to herbicides such as bromoxynil or classes of herbicides such as, for example, HPPD inhibitors, ALS inhibitors such as primisulfuron, prosulfuron and trifloxysulfuron, EPSPS (5-enol-pyrovyl-shikimate-3-phosphate-synthase) inhibitors, GS (glutamine synthetase) inhibitors or PPO (protoporphyrinogen oxidase) inhibitors as a result of conventional methods of breeding or genetic engineering. Examples of crops which have been rendered tolerant to imidazolinones such as imazamox by conventional methods of breeding (mutagenesis) are Summer rapeseed (canola). Examples of crops that have been rendered tolerant to herbicides or herbicides by genetic engineering methods include glyphosate-resistant and glufosinate-resistant maize varieties sold under the trade names Roundup Ready and Commercially available.

[0060] The term "useful plants" is to be understood as also including useful plants which have been transformed by the use of recombinant DNA techniques in such a way that they are able to synthesize one or more selectively acting toxins, such as are known, for example, from toxigenic bacteria, in particular from the genus Bacillus.

[0061] The term "useful plants" should be understood to also include useful plants that have been transformed using recombinant DNA technology so that they can 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 can 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 publications mentioned above.

[0062] The term "locus" of useful plants as used herein is intended to include places where the useful plants grow, where plant propagation material of the useful plants is sown or where plant propagation material of the useful plants will be placed in the soil. Examples of such locations are fields where crop plants grow.

[0063] The term "plant propagation material" should be construed as meaning the reproductive parts of a plant, such as seeds (which can be used for the propagation of plants), and nutritious materials, such as cuttings or tubers (e.g., potatoes). Examples of the term "plant propagation material" include seed (strictly speaking), roots, fruits, tubers, bulbs, rhizomes, and plant parts. Examples of the term "plant propagation material" include germinated plants and young plants that will be transplanted after germination or after emergence. These young plants can be protected before transplanting by being treated completely or in part by dipping. Preferably, "plant propagation material" should be construed as meaning a seed.

[0064] In another aspect, the present application also relates to plant propagation material coated with the composition according to the invention.

[0065] These compositions of the present invention can also be used in the field that protection storage goods is not attacked by fungi.According to the present invention, term " storage goods " should be understood as the natural substance and its processed form of expression plant and / or animal origin, it is taken from natural life cycle and it is hoped to be used for long-term protection.The storage goods of plant origin (such as plant or its part (for example, stalk, leaf, tuber, seed, fruit or grain)) can be protected with the state of fresh harvest or with processed form (such as pre-dried, moistened, pulverized, ground or baked).Also falling under the definition of storage goods is timber, no matter be log form, such as building timber, transmission tower and fence, or be finished product form, such as furniture or object made from timber.The storage goods of animal origin are animal hides, leather, fur, hair etc.Adverse effects can be prevented according to compositions of the present invention, such as corruption, fading or moulding.Preferably, " storage goods " should be understood as the natural substance and / or its processed form of expression plant origin, more preferably fruit and its processed form (such as pome, stone fruit, berry and citrus and its processed form). In another preferred embodiment of the present invention, "stored goods" is understood to mean wood.

[0066] Therefore, another aspect of the present invention is a method for protecting stored goods, which method comprises applying a composition according to the invention to stored goods.

[0067] The compositions according to the invention can also be used in the field of protecting technical materials from fungal attack. According to the present invention, the term "technical materials" includes paper; carpets; buildings; cooling and heating systems; wallboard; ventilation and air conditioning systems, etc.; preferably, "technical materials" is understood to mean wallboard. The compositions according to the invention can prevent adverse effects such as decay, discoloration, or mold.

[0068] Furthermore, the compositions according to the invention are particularly effective against seed-borne and soil-borne diseases, such as Alternaria species, Ascochyta species, Botrytis cinerea, Cercospora species, Claviceps species, Cochliobolus species, Colletotrichum species, Epicococcus species, Fusarium graminearum, Fusarium moniliforme, Fusarium oxysporum, Fusarium laminarum, Fusarium solani, Fusarium gloeosporium, graminis, Helminthosporium sp., Psoralea nivalis, Phoma sp., Pyricularia cereus, Pyricularia oryzae, Rhizoctonia solani, Rhizoctonia graminis, Sclerotinia sp., Psoralea sp., Ustilago officinalis sp., Tilletia sp., Sarcosporium sp., Ustilago officinalis, Ustilago officinalis sp. or Verticillium sp.; in particular against pathogens of cereals, such as wheat, barley, rye or oats; corn; rice; cotton; soybeans; turf; sugar beets; rapeseed; potatoes; legumes, such as peas, lentils or chickpeas; and sunflower.

[0069] Furthermore, the compositions according to the invention are particularly effective against post-harvest diseases such as Botrytis cinerea, Colletotrichum lunata, Fusarium solani, Geotrichum candidum, Psoralea corylifolia, Psoralea corylifolia, Psoralea corylifolia, Mucor pyriformis, Penicillium italicum, Penicillium spp., Penicillium digitatum or Penicillium expansum; in particular against pathogens of fruits such as pome fruits (e.g. apples and pears), stone fruits (e.g. peaches and plums), citrus fruits, melons, papayas, kiwi fruits, mangoes, berries (e.g. strawberries), avocados, pomegranates and bananas, and nuts.

[0070] The compositions according to the invention can be used in particular for controlling the following diseases on the following crops:

[0071] Alternaria species on fruits and vegetables and potatoes; Botrytis cinerea on strawberries, tomatoes, sunflowers, legumes, vegetables and grapes; Rhizoctonia solani in potatoes and vegetables, Leucophyllum viniferum in grapes, Venturia solani, Vulgaris spp., Powdery mildew and Colletotrichum tataricum in cucurbits, Leucophyllum tataricum in cucurbits and Solanaceae crops, Fusarium species in cereals, Septoria species such as Psoralea corylifolia in cereals, Septoria species such as Septoria spp. in oilseed crops, Cercospora species such as Mycosphaerella argentea in tomatoes, legumes, peanuts and oilseed crops, or Cercospora sojinae and Cercospora purpurogenae in soybeans.

[0072] However, in addition to the actual synergistic effect with respect to the fungicidal activity, the compositions according to the invention may also have further unexpected advantageous properties. Examples of such advantageous properties that may be mentioned are: more favorable degradability; improved toxicological and / or ecotoxicological behavior; or improved characteristics of useful plants, including: emergence, crop yield, more developed root system, increased tillering, increased plant height, larger leaves, less basal leaf death, stronger tillers, greener leaves, less fertilizer required, less seed required, more productive tillers, earlier flowering, earlier grain maturity, less plant lodging (lodging), enhanced shoot growth, improved plant vigor and early germination.

[0073] Some compositions according to the invention have systemic action and can be used as fungicides as foliar, soil and seed treatments.

[0074] Using the compositions according to the invention, it is possible to inhibit or destroy phytopathogenic microorganisms which are present on plants or plant parts (fruits, flowers, leaves, stems, tubers, roots) of different useful plants, while also protecting later growing plant parts from attack by phytopathogenic microorganisms.

[0075] The compositions according to the invention can be applied to phytopathogenic microorganisms, useful plants threatened by attack by microorganisms, their locus, their propagation material, stored goods or technical material.

[0076] The compositions according to the invention can be applied before or after the useful plants, their propagation material, stored goods or technical material have been infected by microorganisms.

[0077] The amount of the composition according to the invention to be applied will depend on various factors, such as the compound used; the object of treatment, such as, for example, plants, soil or seeds; the type of treatment, such as, for example, spraying, dusting or seed dressing; the purpose of the treatment, such as, for example, prevention or treatment; the type of fungus to be controlled or the time of application.

[0078] Typically, component (A) is typically applied at a rate of 5 to 2000 g ai / ha, in particular 10 to 1000 g ai / ha, for example 50 g ai / ha, 75 g ai / ha, 100 g ai / ha or 200 g ai / ha when applied to useful plants in combination with component (B) at a rate of typically 1 to 5000 g ai / ha, in particular 2 to 2000 g ai / ha, for example 100 g ai. / ha, 250 g ai / ha, 500 g ai / ha, 800 g ai / ha, 1000 g ai. / ha, 1500 g ai / ha.

[0079] In agricultural practice, the application rates of the compositions according to the invention depend on the type of action desired and typically range from 20 to 4000 g of total composition per hectare.

[0080] When the compositions according to the invention are used to treat seed, ratios of 0.001 to 50 g of compound of component (A) per kg of seed, preferably from 0.01 to 10 g / kg of seed, and 0.001 to 50 g of compound of component (B) per kg of seed, preferably from 0.01 to 10 g / kg of seed are generally sufficient.

[0081] The composition of the present invention can be used in any conventional form, for example, in the form of a two-pack, a dry seed treatment powder (DS), a seed treatment emulsion (ES), a flowable seed treatment concentrate (FS), a seed treatment solution (LS), a seed treatment water-dispersible powder (WS), a seed treatment capsule suspension (CF), a seed treatment gel (GF), an emulsion concentrate (EC), a suspension concentrate (SC), a suspoemulsion (SE), a capsule suspension (CS), a water-dispersible granule (WG), an emulsifiable granule (EG), an oil-in-oil emulsion (EO), an oil-in-water emulsion (EW), a microemulsion (ME), an oil dispersible suspension (OD), an oil suspension (OF), an oil-soluble liquid (OL), a soluble concentrate (SL), an ultra-low volume suspension (SU), an ultra-low volume liquid (UL), a concentrate (TK), a dispersible concentrate (DC), a wettable powder (WP) or any technically feasible formulation in combination with agriculturally acceptable adjuvants.

[0082] Such compositions can be produced in a conventional manner, for example by mixing the active ingredient with at least one suitable inert formulation adjuvant (for example, diluent, solvent, filler and optionally other formulation ingredients, such as surfactants, biocides, antifreeze agents, stickers, thickeners and compounds providing auxiliary effects). Conventional slow-release formulations intended to last for a long time can also be used. In particular, formulations to be applied in a spray form, such as water-dispersible concentrates (for example EC, SC, DC, OD, SE, EW, EO, etc.), wettable powders and granules can contain surfactants such as wetting agents and dispersants and other compounds providing auxiliary effects, for example condensation products of formaldehyde with naphthalene sulfonates, alkylaryl sulfonates, lignin sulfonates, fatty alkyl sulfates and ethoxylated alkylphenols and ethoxylated fatty alcohols.

[0083] The compositions according to the invention may also comprise additional pesticides, such as, for example, fungicides, insecticides or herbicides.

[0084] The composition according to the invention and the diluent are used in the form of a suitable seed dressing formulation, for example an aqueous suspension or dry powder with good adhesion to the seed, in a manner known per se. Such seed dressing formulations are known in the art. Seed dressing formulations may contain a single active ingredient or a combination of active ingredients in encapsulated form, for example as sustained-release capsules or microcapsules.

[0085] Typically, the formulation comprises by weight from 0.01% to 90% active agent, from 0 to 20% agriculturally acceptable surfactant and 10% to 99.99% solid or liquid formulation inert agent and one or more adjuvants, the active agent being composed of at least the compound of component (A) and the compound of component (B), and optionally other active agents (particularly microbicides or preservatives, etc.). Concentrated forms of the composition typically contain by weight between about 2% and 80%, preferably between about 5% and 70% active agent. The application form of the formulation can, for example, contain by weight from 0.01% to 20%, preferably by weight from 0.01% to 5% active agent. However, commercial products will preferably be formulated as concentrates, and end users will typically use diluted formulations.

[0086] The other feature of the composition comprising a compound of formula (I), the method for applying it to plants and its use ratio are as described for the composition comprising a compound of formula (I) and at least one other component (B) as described above. Their application can be before and after these plants or their parts are infected by fungi. Preferably, the treatment is carried out before infection. When the compound of formula (I) is used by itself, the application ratio in the method according to the present invention is as described above, for example, typically 5 to 2000 g ai / ha, particularly 10 to 1000 g ai / ha, for example a ratio of 50, 75, 100 or 200 g ai / ha. During the growing season, the compound of formula (I) can be applied to these plants once or more than once. In order to be used in the method according to the present invention, the compound of formula (I) can be converted into the conventional formulations described above, such as solutions, emulsions, suspensions, dusts, powders, pastes and granules. The form of use will depend on the specific intended purpose; in each case, it should ensure a fine and uniform distribution of the compound of formula (I). The term "plants" as used herein includes seedlings, shrubs and crops of fruits and vegetables.

[0087] The following examples illustrate the present invention, where "active ingredient" refers to a mixture of component (A) and component (B) in a specific mixing ratio. The same formulation can be used for compositions containing only a compound of formula (I) as the active ingredient, as described in the table below.

[0088] Preparation Examples

[0089] Table 1

[0090]

[0091] The active ingredient is thoroughly mixed with the other formulation ingredients and the mixture is thoroughly ground in a suitable grinder to give wettable powders which can be diluted with water to provide a suspension of the desired concentration.

[0092] Table 2

[0093]

[0094] The active ingredient is thoroughly mixed with other formulation components and the mixture is thoroughly ground in a suitable grinder to obtain a dust that can be used directly for seed treatment.

[0095] Table 3

[0096] Emulsifiable concentrates

[0097]

[0098] Emulsions of any desired dilution which can be used in plant protection can be obtained from the concentrates by dilution with water.

[0099] Table 4

[0100]

[0101] Ready-to-use dusts are obtained by mixing the active ingredient with a carrier and grinding the mixture in a suitable grinder. Such dusts can also be used for dry seed dressing.

[0102] Table 5

[0103]

[0104] The active ingredient is mixed and ground with the other formulation components, and the mixture is moistened with water. The mixture is extruded and then dried in a stream of air.

[0105] Suspension concentrate

[0106] Table 6

[0107]

[0108] The finely ground active ingredient is thoroughly mixed with the other formulation components to give a suspension concentrate which can be diluted in water in any desired ratio. Using such dilutions, living plants as well as plant propagation materials can be treated and protected against microbial infestation by spraying, pouring or immersion.

[0109] Flowable concentrate for seed treatment

[0110] Table 7

[0111]

[0112] The finely ground active ingredient is thoroughly mixed with the other formulation components to obtain a suspension concentrate, which can be further diluted in water for application to seeds. Using such dilutions, propagation materials can be treated and protected from microbial infestation by spraying, pouring or dipping.

[0113] Therefore, another aspect of the invention is a method of controlling leaf spot on plants, which method comprises applying to these plants, the locus thereof or their propagation material a composition comprising a compound of formula (I).

[0114] Preferred is a method wherein the plant pathogen is attacking the plant and causing diseases such as leaf spot, powdery mildew and fungal wilt.

[0115] Preferred is a method which comprises applying to the plants or the locus thereof, preferably to the plants, a composition comprising a compound of formula (I).

[0116] Further preferred is a method which comprises applying a composition comprising a compound of formula (I) to the propagation material of these plants. Still further, the present invention also relates to the use of a composition according to the invention for controlling leaf spot on plants.

[0117] The method according to the invention, in particular when using a compound of formula (I) in combination with at least one compound (B) as described above, also allows good control of other frequently encountered harmful fungi in plants.

[0118] Preferred is a method of controlling diseases on oilseeds and cereals, especially caused by leaf spot, which method comprises applying a composition comprising a compound of formula (I) to these useful plants, their locus or their propagation material

[0119]

[0120] where R 1 and R 2 are independently fluoro, chloro or trifluoromethyl, R 3 is methyl or ethyl, A is N and X is C(═O) or O.

[0121] In general, the weight ratio of component (A) to component (B) is in the range of from 2000:1 to 1:1000. The weight ratio of component (A) to component (B) is preferably from 100:1 to 1:100, more preferably from 20:1 to 1:50, even more preferably from 12:1 to 1:25, even more preferably from 10:1 to 1:10, yet more preferably from 5:1 to 1:15, and most preferably from 2:1 to 1:5.

[0122] It has been found that, surprisingly, certain weight ratios of component (A) to component (B) can produce synergistic activity. Therefore, another aspect of the present invention is a composition wherein component (A) and component (B) are present in an amount that produces a synergistic effect. This synergistic activity is evident from the fact that the fungicidal activity of the composition comprising component (A) and component (B) is greater than the sum of the fungicidal activities of component (A) and component (B).

[0123] This synergistic activity extends the spectrum of action of components (A) and (B) in two ways. First, the application rates of components (A) and (B) can be reduced, yet the effect remains equally good, meaning that even in cases where the two individual components become completely ineffective at such low application rates, the active ingredient mixture still achieves a high degree of phytopathogen control. Second, the spectrum of phytopathogens that can be controlled is significantly broadened.

[0124] A synergistic effect exists whenever the effect of the active ingredient combination is greater than the sum of the effects of the individual components. For a given active ingredient combination, the expected effect E obeys the so-called COLBY formula and can be calculated as follows (COLBY, SR "Calculating synergistic and antagonistic responses of herbicide combination". Weeds, Vol. 15, pp. 20-22; 1967):

[0125] ppm = milligrams of active ingredient (=ai) per liter of spray mixture

[0126] X = % effect based on active ingredient A) using p ppm of active ingredient

[0127] Y = % effect based on active ingredient B) using q ppm of active ingredient.

[0128] According to Colby, using p+q ppm of active ingredient, the expected (additive) effect of active ingredient A) + B) is:

[0129]

[0130] If the observed effect (O) is greater than the expected effect (E), then the effect of the combination is superadditive, i.e., a synergistic effect exists. Mathematically, synergism corresponds to a positive value of the difference (OE). In the case of purely complementary additions of active substances (expected activity), the difference (OE) is zero. Negative values of the difference (OE) indicate a loss of activity compared to the expected activity.

[0131] Biological Examples

[0132] Corynespora cassiicola) (target spot of soybean, target leaf spot of tomato):

[0133] Fungal conidia from frozen storage were directly mixed into nutrient broth (PDB potato dextrose broth). DMSO solutions of the test compounds were placed in microtiter plates (96-well format) and the nutrient broth containing the fungal spores was added thereto. These test plates were incubated at 24°C and after 3-4 days, the inhibition of growth was determined photometrically at 620nm. The ratios and results are listed in the table below:

[0134] Table 8

[0135] Compound A-1.3 Cyclobutrifluram Observed Colby (expected) ppm ppm active(%) active(%) 0.03 0 0 0 0.05 50 0 0.025 20 0 0.0125 0 0.03 0.05 70 50 0.03 0.025 20 20 0.03 0.0125 20 0

[0136] Table 9

[0137] Compound A-1.3 pyraclostrobin Observed Colby (expected) ppm ppm active(%) active(%) 0.2 0 20 0 1 70 0 0.5 20 0.2 1 90 76 0.2 0.5 50 36

[0138] Mycosphaerella arachidis (Cercospora arachidis) arachidicola) (brown leaf spot of peanut):

[0139] Fungal conidia from frozen storage were mixed directly into nutrient broth (PDB potato dextrose broth). DMSO solutions of test compounds were placed in microtiter plates (96-well format) and the nutrient broth containing the fungal spores was added thereto.

[0140] The test plates were incubated at 24° C. and the inhibition of growth was determined photometrically at 620 nm after 5-6 days.

[0141] Table 10

[0142] Compound A-1.3 Benpyraclostrobin Observed Colby (expected) Ppm ppm active(%) active(%) 0.03 0 50 0 20 0 0 10 0 0 5 0 0 2.5 0 0.03 20 70 50 0.03 10 70 50 0.03 5 70 50 0.03 2.5 70 50

[0143] Septoria wheat (leaf blister disease):

[0144] Fungal conidia from frozen storage were directly mixed into nutrient broth (PDB potato dextrose broth). DMSO solutions of the test compounds were placed in microtiter plates (96-well format) and the nutrient broth containing the fungal spores was added thereto. These test plates were incubated at 24° C. and after 72 hours, the inhibition of growth was determined photometrically.

[0145] Table 11

[0146]

[0147]

[0148] Table 12

[0149] Compound A-1.3 pyraclostrobin Observed Colby (expected) Ppm ppm active(%) active(%) 0.06 0 70 0 1 90 0 0.5 70 0 0.25 0 0 0.125 0 0 0.0625 0 0.06 1 100 97 0.06 0.5 100 91 0.06 0.25 100 70 0.06 0.125 90 70 0.06 0.0625 90 70

[0150] Septoria soybean (brown spot disease):

[0151] Fungal conidia from frozen storage were directly mixed into nutrient broth (PDB potato dextrose broth). DMSO solutions of the test compounds were placed in microtiter plates (96-well format) and the nutrient broth containing the fungal spores was added thereto. These test plates were incubated at 24° C. and visually determined for growth inhibition after 72 hours.

[0152] Table 13

[0153]

[0154]

[0155] Table 14

[0156] Compound A-1.3 Cyclobutrifluram Observed Colby (expected) Ppm ppm active(%) active(%) 0.06 0 20 0 0.2 90 0 0.1 70 0 0.05 70 0 0.025 50 0 0.0125 20 0.06 0.2 100 92 0.06 0.1 100 76 0.06 0.05 100 76 0.06 0.025 70 60 0.06 0.0125 50 36

[0157] Table 15

[0158] Compound A-1.3 Florylpicoxamid Observed Colby (expected) Ppm ppm active(%) active(%) 0.03 0 0 0 0.1 90 0 0.05 70 0.03 0.1 100 90 0.03 0.05 90 70

[0159] Table 16

[0160]

[0161]

[0162] Table 17

[0163] Compound A-1.3 Mandestrobin Observed Colby (expected) Ppm ppm active(%) active(%) 0.03 0 0 0 0.5 90 0 0.25 70 0 0.125 50 0.03 0.5 100 90 0.03 0.25 100 70 0.03 0.125 70 50

[0164] Table 18

[0165] Compound A-1.3 Mandestrobin Observed Colby (expected) Ppm ppm active(%) active(%) 0.06 0 20 0 1 90 0 0.5 70 0 0.25 70 0.06 1 100 92 0.06 0.5 90 76 0.06 0.25 70 76

[0166] Table 19

[0167]

[0168]

[0169] Table 20

[0170] Compound A-1.3 Fluopyram Observed Colby (expected) ppm ppm active(%) active(%) 0.06 0 20 0 20 0 0 10 0 0 5 0 0 2.5 0 0 1.25 0 0.06 20 70 20 0.06 10 70 20 0.06 5 50 20 0.06 2.5 50 20 0.06 1.25 50 20

[0171] Table 21

[0172]

[0173]

[0174] Table 22

[0175] Compound A-1.3 Benthiostrobin Observed Colby (expected) ppm ppm active(%) active(%) 0.06 0 20 0 0.2 90 0 0.1 90 0 0.05 90 0 0.025 70 0 0.0125 50 0.06 0.2 100 92 0.06 0.1 100 92 0.06 0.05 100 92 0.06 0.025 90 76 0.06 0.0125 70 60

[0176] Table 23

[0177]

[0178]

Claims

1. A composition suitable for controlling diseases caused by plant pathogens, comprising: (A) a compound having formula I: where R 1 It is chlorine and R 2 is trifluoromethyl, R 3 is methyl, A is N and X is O, i.e., methyl 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoate; or an agrochemically acceptable salt thereof, and (B) at least one compound selected from the group consisting of benzathiapiprolin, trifluopyram, pyridamole, fluopyram, ipflufenoquin, mandestrobin, metyltetraprole, pyraclostrobin and pyraclostrobin, or a combination thereof, in, The weight ratio of (A) to (B) is in the range of from 100:1 to 1:

100.

2. The composition according to claim 1, wherein The weight ratio of (A) to (B) is in the range of from 20:1 to 1:

40.

3. The composition according to claim 2, wherein The weight ratio of (A) to (B) is in the range of from 12:1 to 1:

25.

4. The composition according to claim 3, wherein The weight ratio of (A) to (B) is in the range of from 5:1 to 1:

15.

5. The composition according to claim 1, wherein The composition comprises at least one or more additional insecticidal, acaricidal, nematicidal and / or fungicidal active agents.

6. The composition according to claim 5, wherein The one or more additional active agents comprise one or more pesticides selected from at least one compound selected from the group consisting of pyridoxamide, fluopicolide, mandestrobin, metyltetraprole, benpyrad and pyraclostrobin, wherein the at least one or more additional pesticides are selected from the group defined above, but are different from component (B).

7. The composition of claim 1, further comprising an agriculturally acceptable carrier, and optionally a surfactant and / or one or more formulation adjuvants.

8. A method for controlling diseases on useful plants or on their propagation material caused by phytopathogens, which method comprises applying a composition according to any one of claims 1 to 7 to the useful plants, the locus thereof or their propagation material.

9. The method according to claim 8, wherein Components (A) and (B) of the composition are applied simultaneously, intermittently or sequentially.

10. Use of the composition according to any one of claims 1 to 7 in the preparation of a coating agent for plant propagation materials.

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