Method for controlling or preventing plants from being infected by plant pathogenic microorganisms such as Corynepora polytomata, soybean gray spot pathogen and / or soybean purple spot pathogen

Abstract

The present invention relates to methods for controlling or preventing plants from being infected by plant pathogenic microorganisms such as Coryneformis multilocus, gray leaf spot pathogen of soybean and / or purple leaf spot pathogen of soybean, which methods comprise applying a fungicidally effective amount of a compound as defined in claim 1 to the plant pathogen, the site of the plant pathogen, or a plant susceptible to the attack of the plant pathogen, or its propagation material.

Description

[0001] The present invention relates to a method for controlling or preventing plants from being infected by plant pathogenic microorganisms Corynespora cassicola, Cercospora sojina and / or Cercospora akikuchii.

[0002] Coryneformis infects more than 530 species in 53 families (Dixon, LJ, et al., 2009, Phytopathology 99(9)1015-27). It is most common in tropical and subtropical areas. It has also been isolated from nematodes and human skin. Coryneformis is considered a pathogen of many crop plants, such as beans, cowpeas, cucumbers, papayas, soybeans,

[0003] Sweet potato and tomato. On several plants, such as tomatoes, the disease caused by Corynepora polytomata is known as target leaf spot or target spot. Similarly, Pseudomonas aeruginosa causes so-called leaf blight in many plants, while gray leaf spot is caused by Pseudomonas aeruginosa, both of which are also common diseases of many plants, especially soybeans in most soybean-growing countries of the world. Substantial soybean yield losses of up to 60% are due to target leaf spot, gray leaf spot and / or leaf blight, especially under hot and humid growing conditions.

[0004] Pseudomonas aeruginosa is a fungal plant pathogen that affects soybean plants. Pseudomonas aeruginosa causes Cercospora leaf blight and purple spot on soybeans. These diseases are found throughout the world. Pseudomonas aeruginosa infects the leaves, stems, and pods of the host plant. Cercospora leaf blight is an economically important disease and can cause substantial yield losses. Purple spot affects seed quality and can result in reduced yields (stands).

[0005] Gray leaf spot is a fungal plant pathogen that causes gray leaf spot on soybean. Gray leaf spot is a major disease on soybeans in the southern United States and has recently begun to expand into soybean-growing areas of the northern United States. The disease has also been found in other soybean-producing regions of the world.

[0006] The development of resistance of the plant pathogens Corynespora multilocus, gray leaf spot of soybean, and / or purple leaf spot of soybean to many current commercial solutions limits their utility and, while the development of new classes of agrochemical fungicides is ongoing, many of these new chemical classes are limited in their fungicidal spectrum and can only control certain specific plant pathogens. That is, when a new chemical class is demonstrated to control certain specific plant pathogens on certain specific crops, it cannot be expected that the same chemical class will prove useful for controlling the plant pathogens Corynespora multilocus, gray leaf spot of soybean, and / or purple leaf spot of soybean, for example, on soybeans.

[0007] Therefore, there is a need to develop new methods for controlling or preventing infection by the plant pathogens Corynespora multilocus, gray leaf spot pathogen, and / or purple leaf spot pathogen. DETAILED DESCRIPTION

[0008] 2-[2-(7,8-difluoro-2-methylquinolin-3-yloxy)-6-fluorophenyl]propan-2-ol and closely related compounds and methods for their preparation are disclosed in WO 2011081174. It has now been surprisingly found that the specific quinoline compounds disclosed in WO 2011081174 are very effective in controlling or preventing infection of plants by the plant pathogenic microorganisms Coryneformis, Gray Spot Pathogen of Soybean and / or Purple Spot Pathogen of Soybean. Therefore, these very effective compounds provide farmers with an important new solution for controlling or preventing infection of plants by the plant pathogenic microorganisms Coryneformis, Gray Spot Pathogen of Soybean and / or Purple Spot Pathogen of Soybean.

[0009] Therefore, as shown in Example 1, a method for controlling or preventing plants from being infected by plant pathogenic microorganisms such as Coryneformis, Gray Spot Pathogen and / or Purple Spot Pathogen is provided, the method comprising applying a fungicidally effective amount of 2-[2-(7,8-difluoro-2-methylquinolin-3-yloxy)-6-fluorophenyl]propan-2-ol to the plant pathogens, the sites of the plant pathogens, or the plants susceptible to the plant pathogens, or their propagation materials.

[0010] A process for preparing the compound as described in Example 1 is described in WO 2011081174. A more preferred process according to Example 1 is given in the following examples.

[0011] The skilled person knows that according to the method of the present invention, the compound is usually applied as part of a pesticidal composition. Therefore, as in Example 2, a method for controlling or preventing plants from being infected by plant pathogenic microorganisms such as Coryneformis multilocus, soybean gray spot fungus and / or soybean purple spot fungus is provided, the method comprising applying a pesticidal composition to plant pathogens, plant pathogen sites, or plants susceptible to plant pathogen attacks, or their propagation materials, the pesticidal composition comprising a compound as defined above and one or more formulation adjuvants.

[0012] As embodiment 3, there is provided a method according to any one of embodiments 1 or 2, the method comprising the steps of: providing a composition comprising a compound as defined in any one of embodiments 1 or 2; and applying the composition to a propagation material; and planting the propagation material.

[0013] As embodiment 4, a method according to any one of embodiments 1 to 3 is provided, comprising the following steps: providing a composition comprising a compound as defined above; applying the composition to a plant pathogen, a locus of a plant pathogen, or a plant susceptible to attack by a plant pathogen.

[0014] As embodiment 5, there is provided use of a compound as defined in any one of embodiments 1 to 4 for controlling or preventing plants from being infected by the plant pathogenic microorganism Corynespora multilocus.

[0015] As embodiment 6, a method or use according to any one of embodiments 1 to 5 is provided, wherein the plant is selected from beans, cowpeas, cucumbers, papayas, soybeans, sweet potatoes, tomatoes, cotton, eggplants, basil, thyme, rubber trees, pawpaw trees, azaleas and hydrangeas.

[0016] As embodiment 7, provided is a method or use according to any one of embodiments 1 to 6, wherein the plant is selected from beans, cowpeas, cucumbers, papayas, soybeans, sweet potatoes and tomatoes.

[0017] As embodiment 8, there is provided a method or use according to any one of embodiments 1 to 7, wherein the plant is soybean. The preparation of the compound defined in the method as defined in any one of embodiments 1 to 8 has been disclosed in WO 2011 / 081174, which is incorporated herein by reference.

[0018] As in Example 9, the present invention also preferably relates to a pesticidal composition suitable for controlling diseases caused by plant pathogens, comprising:

[0019] (A) a fungicidally effective amount of 2-[2-(7,8-difluoro-2-methylquinolin-3-yloxy)-6-fluorophenyl]propan-2-ol, its N-oxide and agriculturally acceptable salts; and at least one or more compounds (B) selected from other biologically active agents such as bactericides, fungicides, nematicides, plant activators, miticides and insecticides, one or more adjuvants, and diluents or carriers.

[0020] Preferred compounds (B) include 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol; 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol (these compounds can be prepared by the method described in WO 2017 / 029179); 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile; 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile (these compounds can be prepared by the method described in WO 2016 / 156290); (4-phenoxyphenyl)methyl 2-amino-6-methyl-pyridine-3-carboxylate (this compound can be prepared by the method described in WO 2014 / 006945); 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetraone (this compound can be prepared by the method described in WO 2011 / 138281);

[0021] Further preferred compounds (B) include N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiobenzamide; N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide; (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamine (this compound can be prepared by the method described in WO 2018 / 153707); N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine; N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine (these compounds can be prepared by the method described in WO 2-(Difluoromethyl)-N-[(3S)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (this compound can be prepared by the method described in WO 2014 / 095675);

[0022] 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridinyl]-1-(1,2,4-triazol-1-yl)propan-2-ol is disclosed in WO 2017 / 029179; 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3-pyridinyl]oxy]benzonitrile is disclosed in WO 2016 / 187201; N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine is disclosed in WO 2017 / 005710; N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine is disclosed in WO 2016 / 202742;

[0023] N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiobenzamide is disclosed in WO 2017 / 211649; 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide is disclosed in WO 2017 / 076742; N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide is disclosed in WO 2015 / 185485; Zhongshengmycin, thiophanate-methyl, zinc thiazole, amitolin, isoprodinil; fluoxapiprolin, enoxastrobin; trinexapac-ethyl; syringystrobin; syringystrobin; (4-phenoxyphenyl)methyl 2-amino-6-methyl-pyridine-3-carboxylate (aminopyrifen); N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiobenzamide; N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide; (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide (Strobiluri ne); N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine; 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile; 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile; 2-(difluoromethyl)-N- (3-Ethyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide; (E)-3-methoxy-2-[2-[(5-methoxy-1,3-benzothiazol-2-yl)sulfanylmethyl]phenyl]prop-2-enoic acid methyl ester; 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile;

[0024] 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3-pyridinyl]oxy]benzonitrile; 3-(3,4-dichloro-1,2-thiazol-5-ylmethoxy)-1,2-benzothiazole 1,1-dioxide (dichlorobenzothiazole); (2E)-2-{2-[({[(2E,3E)-4-(4-chlorophenyl)but-3-en-2-ylidene]-amino}oxy)methyl]phenyl}-3-methoxyprop-2-enoic acid methyl ester (enoxamyl); 2Z)-2-[2-[[(E)-[(E)-4-(2,6-dichlorophenyl)but-3-en-2-ylidene]amino]oxymethyl [(1S)-2,2-bis(4-fluorophenyl)-1-methyl-ethyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate (pyrithione); 3-(difluoromethyl)-N-[(3RS)-7-fluoro-2,3-dihydro-1,1,3-trimethyl-1H- Indane-4-yl]-1-methyl-1H-pyrazole-4-carboxamide (flufenazol); 3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide (Inpyrfluxam); (2RS)-2-[4-(4-chlorophenoxy)-α,α,α-trifluoro-o-tolyl]-3-methyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol (Ipfentrifluconazole); 2-[2-[(7,8-difluoro-2-methyl-3-quinolyl)oxy]-6-fluoro-phenyl]propan-2-ol (Ipfentrifluconazole); 2-[2-[(2, 5-Dimethylphenoxy)methyl]phenyl]-2-methoxy-N-methyl-acetamide (Mandestrobin); (2RS)-2-[4-(4-chlorophenoxy)-α,α,α-trifluoro-o-tolyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol (Clofluanidazole); 1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one (Metyltetraprole); Methyl N-[2-[(2,4-dimethyl-5-phenylpyrazol-3-yl)oxymethyl]phenyl]-N-methoxycarbamate (Imidazolidinone);(E)-2-[2-[[5-(4-chlorophenyl)-2-methylpyrazol-3-yl]oxymethyl]phenyl]-3-methoxyprop-2-enoic acid methyl ester (pyrapropoxystrobin); (Z)-N-{2-[3-chloro-5-(cyclopropylethynyl)-2-pyridinyl]-2-(isopropoxyimino)ethyl}-3-(difluoromethyl)-1-methylpyrazole-4-carboxamide (pyrapropoyne); N-methoxy-N-[2-[(3,5 ,6-trichloropyridin-2-yl)oxymethyl]phenyl]carbamic acid methyl ester (Chlorpyroxithrin); N-[2-[2,4-dichloro-phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide (Lvbenmixianan); N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]-phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide (Fubenmixianan);

[0025] N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1, 2,4-oxadiazol-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]-methyl]propionamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-isoxazolidin-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl] [[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-isoxazolidin-3-one, 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylic acid ethyl ester, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-1,2,4-triazol-3-amine. These compounds in this paragraph can be prepared according to the methods described in WO 2017 / 055473, WO 2017 / 055469, WO 2017 / 093348 and WO2017 / 118689.

[0026] Preferred compounds (B) include 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl- N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiobenzamide, 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide and N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide.

[0027] Particularly preferred are (4-phenoxyphenyl)methyl 2-amino-6-methyl-pyridine-3-carboxylate (aminopyridine); 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetraone; N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiobenzamide; N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide; (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide; N'- (2-Chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine; N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine; N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine; N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine; 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridinyl]-1-(1,2,4-triazol-1-yl)propan-2-ol; 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridinyl]-1-(1,2,4-triazol-1-yl)propan-2-ol 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile; 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile; 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide; (E)-3-methoxy-2-[2-[(5-methoxy-1,3-benzothiazol-2-yl)sulfanylmethyl]phenyl]prop-2-enoic acid methyl ester; 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2- hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridinyl]oxy]benzonitrile; 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3-pyridinyl]oxy]benzonitrile; 3-(3,4-dichloro-1,2-thiazol-5-ylmethoxy)-1,2-benzothiazole 1,1-dioxide; (3S,6S,7R,8R)-8-benzyl-3-{3-[(isobutyryloxy)methoxy]-4-methoxypyridine-2-carboxamido}-6-methyl-4,9-dioxo-1,5-dioxacyclononan-7-yl isobutyrate;[(1S)-2,2-bis(4-fluorophenyl)-1-methyl-ethyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate; 3-(difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl-indan-4-yl)-1-methyl-pyrazole-4-carboxamide; [2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]thiazol-4-yl]-4,5-dihydroisoxazol-5-yl]-3-chloro-phenyl]methanesulfonate; 3-(difluoromethyl)-1-methyl-N-[(3R)-1, 1,3-Trimethylindan-4-yl]pyrazole-4-carboxamide; (2RS)-2-[4-(4-chlorophenoxy)-α,α,α-trifluoro-o-tolyl]-3-methyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol; 2-[2-[(7,8-difluoro-2-methyl-3-quinolyl)oxy]-6-fluoro-phenyl]propan-2-ol; N-[1,1-dimethyl-2-(4-isopropoxy-o-tolyl)-2-oxoethyl]-3-methylthiophene-2-carboxamide; N-[(5-chloro-2-isopropyl-phenyl)methyl]-N-cyclopropyl-3-(difluoromethyl)-5- Fluoro-1-methyl-pyrazole-4-carboxamide; 2-[2-[(2,5-dimethylphenoxy)methyl]phenyl]-2-methoxy-N-methyl-acetamide; (2RS)-2-[4-(4-chlorophenoxy)-α,α,α-trifluoro-o-tolyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol; 1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one; (Z)-N-{2-[3-chloro-5-(cyclopropylethynyl)-2-pyridinyl]-2-(isopropoxyimino)ethyl}-3-( N-[2-(3,4-difluorophenyl)phenyl]-3-(trifluoromethyl)pyrazine-2-carboxamide; 3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine; 3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1-yl)quinoline; N-[2-[2,4-dichloro-phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide; and / or N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide. ;

[0028] In each case, the compound of formula I according to the present invention is in free form, oxidized form such as N-oxide, or salt form (e.g., agronomically useful salt form). N-oxides are oxidized forms of tertiary amines or oxidized forms of nitrogen-containing heteroaromatic compounds. For example, A. Albini and S. Pietra described them in a book entitled "Heterocyclic N-oxides" published by CRC Press, Boca Raton, in 1991. The present invention also relates to all stereoisomers and mixtures thereof in any ratio.

[0029] Preferred compositions comprising (A) a compound of formula I are as listed above in Ia, Ib and / or Ic; and (B) at least one compound selected from the group consisting of 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridinyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiobenzamide and N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide.

[0030] It has been found that the use of component (B) in combination with component (A) unexpectedly and substantially enhances the effect of the latter against fungi and vice versa. In addition, the method of the invention is effective against a wider spectrum of such fungi than the active ingredients of this method can combat when used alone.

[0031] Another aspect of the present invention is a method for controlling diseases caused by plant pathogens on useful plants or on their propagation materials, the method comprising applying a composition according to the present invention to useful plants, their place or their propagation materials. Preferably, the following method comprises applying a composition according to the present invention to useful plants or their place, more preferably to useful plants. Also preferably, the following method comprises applying a composition according to the present invention to the propagation material of useful plants.

[0032] Throughout this document, the expression "composition" refers to 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 individual active ingredients when applied in a sequential manner (i.e., one after another within a reasonably short period of time, such as a few hours or days). For the implementation of the present invention, the order of applying components (A) and (B) is not important.

[0033] The compositions according to the invention are effective against unwanted microorganisms, such as microorganisms causing phytopathogenic diseases, in particular against phytopathogenic fungi and bacteria.

[0034] Preferably, a formulation comprising a composition according to the invention may comprise from 0.01% to 90% by weight of a composition comprising compounds (A) and (B), and from 0% to 20% of an agriculturally acceptable surfactant. Preferably, the formulation further comprises other active agents, more generally, in particular microbicides and pesticides.

[0035] Advantageously, the formulation further comprises from 10% to 99.99% of solid or liquid formulation inerts, preservatives and / or adjuvants.

[0036] The invention preferably also relates to a concentrated composition for dilution by the user, comprising a composition according to the invention or a formulation according to the invention comprising from 2 to 80% by weight, preferably between 5 and 70% by weight, of active agents, these active agents comprising at least a composition containing (A) and (B), and optionally further active agents.

[0037] The method, composition and use as described in any one of Examples 1 to 9 are preferably used to control or prevent crops from being infected by plant pathogenic microorganisms such as Coryspora multinomialis, gray spot disease of soybean and / or purple spot disease of soybean that are resistant to other fungicides. Coryspora multinomialis, gray spot disease of soybean and / or purple spot disease of soybean that are "resistant" to a specific fungicide refer to, for example, Coryspora multinomialis, gray spot disease of soybean and / or purple spot disease of soybean that are less sensitive to that fungicide compared to the expected sensitivity of the same Coryspora multinomialis fungal species. The expected sensitivity can be measured using, for example, strains that have not been previously exposed to fungicides. An "effective" amount herein refers to the amount of active ingredients that show sufficient biocidal activity compared to a blind test, for example, at least 10%, more preferably at least 20%, more preferably at least 50%, and more preferably at least 70% effectiveness again. In the present case, the composition according to the invention preferably comprises at least 0.01 ppm, more preferably at least 0.025 ppm of active ingredient, more preferably at least 6 ppm, 3 ppm, 2.2 ppm, 1.5 ppm, 0.8 ppm, 0.74 ppm, 0.25 ppm, 0.2 ppm, or 0.082 ppm is applied.

[0038] According to the method or use according to any one of embodiments 1 to 9, preferably applied to plant crops, their place or their propagation materials. Preferably applied to plant pathogens, the place of plant pathogens, or plants susceptible to plant pathogens, or their propagation materials. The application of the compound as defined in any one of embodiments 1 to 13 can be carried out according to any common application mode (e.g., leaf application, drench application, soil application, in-furrow application, etc.).

[0039] The compounds as defined in any one of embodiments 1 to 13 are preferably used for pest control at a rate of 1 to 500 g / ha, preferably 50-300 g / ha.

[0040] The compounds as defined in any one of embodiments 1 to 13 are suitable for use on any plant, including those that have been genetically modified to be resistant to active ingredients such as herbicides, or those that have been genetically modified to produce biologically active compounds that control infestation by plant pests.

[0041] Typically, the compound as defined in Example 1 is used in the form of a composition (eg, formulation) containing a carrier. The compounds and compositions thereof as defined in Example 1 can be used in different forms, such as aerosol sprays, capsule suspensions, concentrated cold mists, dustable powders, emulsifiable concentrates, oil-in-water emulsions, water-in-oil emulsions, encapsulated granules, fine granules, flowable concentrates for seed treatment, gases (under pressure), gas-producing products, granules, concentrated hot mists, large granules, microgranules, oil-dispersible powders, oil suspensions, oil-soluble liquids, pastes, plant sticks, powders for dry seed treatment, seeds coated with pesticides, soluble concentrates, soluble powders, solutions for seed treatment, suspension concentrates (flowable concentrates), ultra-low volume (ulv) liquids, ultra-low volume (ulv) suspensions, water-dispersible granules or tablets, water-dispersible powders for slurry treatment, water-soluble granules or tablets, water-soluble powders for seed treatment and wettable powders.

[0042] The compositions of the present invention, including all of the above disclosed embodiments and preferred examples thereof, may be mixed with one or more additional pesticides, including additional fungicides, insecticides, nematicides, bactericides, acaricides, growth regulators, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants or other biologically active compounds to form multi-component pesticides giving a broader spectrum of agricultural protection.

[0043] The formulation typically comprises a liquid or solid carrier and optionally one or more conventional formulation adjuvants, which may be solid or liquid adjuvants, for example, unepoxidized or epoxidized vegetable oils (e.g., epoxidized coconut oil, rapeseed oil or soybean oil), defoamers (e.g., silicone oils), preservatives, clays, inorganic compounds, viscosity modifiers, surfactants, binders and / or tackifiers. The composition may further comprise fertilizers, micronutrient donors or other agents that influence plant growth, and combinations containing the compounds of the invention and one or more other biologically active agents, such as bactericides, fungicides, nematicides, plant activators, acaricides and insecticides.

[0044] The compositions are prepared in a manner known per se, in the absence of auxiliaries, for example by grinding, sieving and / or compressing the solid compound according to the invention, and in the presence of at least one auxiliary, for example by intimately mixing and / or grinding the compound according to the invention with one or more auxiliary agents. In the case of the solid compounds according to the invention, the grinding / milling of the compound is to ensure a specific particle size.

[0045] Examples of compositions for use in agriculture are emulsifiable concentrates, suspension concentrates, microemulsions, oil dispersions, directly sprayable or dilutable solutions, spreadable pastes, diluted emulsions, soluble powders, dispersible powders, wettable powders, dusts, granules or capsules in a polymeric substance, these compositions comprising at least a compound as defined in any one of embodiments 1 to 4 and the type of composition being chosen to suit the intended purpose and the prevailing circumstances.

[0046] Typically, the composition comprises 0.1% to 99% (especially 0.1% to 95%) of a compound as defined in any one of Examples 1 to 14 and 1% to 99.9% (especially 5% to 99.9%) of at least one solid or liquid carrier, and it is usually possible that 0 to 25% (especially 0.1% to 20%) of the composition is a surfactant (% means percentage by weight in each case). Although for commercial products, concentrated compositions tend to be preferred, the final consumer usually uses a dilute composition with a significantly lower concentration of active ingredients.

[0047] Regarding the composition comprising component (A) and component (B); Generally speaking, the weight ratio of component (A) to component (B) is 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, even more preferably from 5: 1 to 1: 15, and most preferably from 2: 1 to 1: 5.

[0048] It has been found that, unexpectedly, formulations comprising a specific weight ratio 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 the composition 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). This synergistic activity extends the scope of action of component (A) and component (B) in two ways. First, the application ratio of component (A) and component (B) is reduced, but the effect remains equally good, which means that even if the two separate components have become completely ineffective within such a low application ratio range, the active ingredient mixture still achieves a high degree of plant pathogen control. Second, the spectrum of plant pathogens that can be controlled is greatly widened.

[0049] 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):

[0050] ppm = milligrams of active ingredient (=ai) per liter of spray mixture

[0051] X = % effect based on active ingredient A) using p ppm of active ingredient

[0052] Y = % effect based on active ingredient B) using q ppm of active ingredient.

[0053] According to Kolby, using p+q ppm of active ingredient, the expected (additive) effect of active ingredient A) + B) is

[0054] If the effect actually observed (O) is greater than the expected effect (E), then the effect of the combination is superadditive, i.e. there is a synergistic effect. In mathematical terms, synergy corresponds to a positive value of the difference (OE). In the case of purely complementary additions of actives (expected activity), the difference (OE) is zero. Negative values ​​of the difference (OE) indicate a loss of activity compared to the expected activity.

[0055] 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 tillering, greener leaf color, less fertilizer required, less seed required, more productive tillering, earlier flowering, earlier grain maturity, less plant lodging (lodging), enhanced shoot growth, improved plant vigor and early germination.

[0056] An additional beneficial effect may be the inhibition or reduction of the development of resistance to a certain active ingredient, which may be particularly beneficial through combinations that may have one or more different modes of action.

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

[0058] 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.

[0059] 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 technological material.

[0060] 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 with the microorganisms.

[0061] 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.

[0062] 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), preferably 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.

[0063] 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.

[0064] When the composition according to the invention is used to treat seed, a rate 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 preferably 0.001 to 50 g of compound of component (B) per kg of seed, preferably from 0.01 to 10 g / kg of seed is generally sufficient.

[0065] Examples of leaf formulation types for use in premix compositions are:

[0066] GR: Granules

[0067] WP: Wettable Powder

[0068] WG: Water dispersible granules (powder)

[0069] SG: Water-soluble granules

[0070] SL: Soluble Concentrate

[0071] EC: Emulsifiable Concentrate

[0072] EW: Oil in water emulsion

[0073] ME: Microemulsion

[0074] SC: Aqueous Suspension Concentrate

[0075] CS: Aqueous Capsule Suspension

[0076] OD: Oil-based suspension concentrates, and

[0077] SE: aqueous suspension emulsion.

[0078] While examples of the types of seed treatment formulations useful in premix compositions are:

[0079] WS: Wettable powder for seed treatment slurry

[0080] LS: Solution for seed treatment

[0081] ES: Emulsion for seed treatment

[0082] FS: Suspension concentrate for seed treatment

[0083] WG: water dispersible granules, and

[0084] CS: aqueous capsule suspension.

[0085] Examples of formulation types suitable for tank-mix compositions are solutions, dilute emulsions, suspensions or mixtures thereof, and dusts.

[0086] In view of the nature of the formulation, the application method (such as foliar application, drenching application, spraying application, atomization application, dusting application, broadcasting application, coating application or pouring application) can be selected according to the intended purpose and the prevailing circumstances.

[0087] Tank-mix compositions are typically prepared by diluting one or more premix compositions containing different pesticides and, optionally, additional adjuvants with a solvent (eg, water).

[0088] Suitable carriers and adjuvants can be solid or liquid and are the substances customary in formulation technology, for example natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers.

[0089] Generally, tank-mix formulations for foliar or soil application contain 0.1% to 20%, especially 0.1% to 15%, of the desired ingredients and 99.9% to 80%, especially 99.9% to 85%, of solid or liquid adjuvants (including, for example, diluents or solvents such as water), wherein the adjuvant may be a surfactant, in an amount of 0 to 20%, especially 0.1% to 15%, based on the tank-mix formulation.

[0090] Typically, premix formulations for foliar application contain 0.1% to 99.9%, especially 1% to 95%, of the desired ingredient and 99.9% to 0.1%, especially 99% to 5%, of a solid or liquid adjuvant (including, for example, a solvent such as water), wherein the adjuvant may be a surfactant, in an amount of 0 to 50%, especially 0.5% to 40%, based on the premix formulation.

[0091] Typically, tank-mix formulations for seed treatment applications contain 0.25% to 80%, especially 1% to 75%, of the desired ingredients and 99.75% to 20%, especially 99% to 25%, of solid or liquid adjuvants (including, for example, solvents such as water), wherein the adjuvant may be a surfactant, in an amount of 0 to 40%, especially 0.5% to 30%, based on the tank-mix formulation.

[0092] Typically, premix formulations for seed treatment applications contain 0.5% to 99.9%, especially 1% to 95% of the desired ingredients and 99.5% to 0.1%, especially 99% to 5%, of solid or liquid adjuvants (including, for example, solvents such as water), wherein the adjuvant can be a surfactant, in an amount of 0 to 50%, especially 0.5% to 40%, based on the premix formulation.

[0093] Whereas commercial products will preferably be formulated as concentrates (eg, premix compositions (formulations)), the end user will typically use a diluted formulation (eg, a tank-mix composition).

[0094] Preferred seed treatment premix formulations are aqueous suspension concentrates. Conventional processing techniques and machines can be used, such as fluidized bed technology, drum milling method, static rotation (rotostatic) seed treatment machine and drum coating machine, and the formulation is applied to the seed. Other methods (such as spouted bed) may also be useful. Seeds can be pre-sized before coating. After coating, the seeds are typically dried and then transferred to the sizing machine for sizing. Such procedures are known in the art. The compound of the present invention is particularly suitable for soil and seed treatment application. Typically, the premix composition of the present invention contains 0.5% to 99.9%, especially 1% to 95%, advantageously 1% to 50% of the desired ingredients and 99.5% to 0.1%, especially 99% to 5% of solid or liquid adjuvants (including, for example, solvents, such as water) by mass, wherein the adjuvant (or adjuvant) can be a surfactant, and its amount is based on the mass of the premix formulation by mass 0 to 50%, especially 0.5% to 40%.

[0095] In addition, further, other biocidal active ingredients or compositions can be combined with the composition of the present invention, and used in the method of the present invention and applied simultaneously or sequentially with the composition of the present invention. When applied simultaneously, these other active ingredients can be prepared or mixed in, for example, a spray tank together with the composition of the present invention. These other biocidal active ingredients can be fungicides, herbicides, insecticides, bactericides, acaricides, nematicides and / or plant growth regulators.

[0096] In addition, the compositions of the invention may also be administered with one or more inducers of systemic acquired resistance ("SAR" inducers). SAR inducers are known and described, for example, in U.S. Pat. No. 6,919,298 and include, for example, salicylates and the commercial SAR inducer acibenzolar-S-methyl.

[0097] The compounds as defined in Example 1 are usually used in the form of compositions and can be applied to the crop area or the plants to be treated simultaneously or sequentially with other compounds. For example, these other compounds can be fertilizers or micronutrient donors or other preparations that influence plant growth. They can also be selective or non-selective herbicides, together with insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, if desired together with other carriers, surfactants or adjuvants that facilitate application that are usually used in the field of formulations.

[0098] The compounds of formula (I) can be used in the form of (fungicide) compositions for controlling or protecting against the phytopathogenic microorganism Coryneformis, which compositions contain as active ingredients a compound as defined in Example 1 (in free form or in the form of agrochemically acceptable salts) and at least one of the above-mentioned adjuvants.

[0099] Plants and / or target crops according to the present invention include conventional as well as genetically enhanced or genetically engineered varieties, such as, for example, insect-resistant (e.g., Bt. and VIP varieties) as well as disease-resistant, herbicide-tolerant (e.g., glyphosate-resistant and glufosinate-resistant corn varieties, marketed under the trade name Roundup Ready and LibertyLink Commercially available) and nematode-tolerant varieties. By way of example, suitable genetically enhanced or genetically engineered crop varieties include Stoneville 5599BR cotton and Stoneville 4892BR cotton varieties.

[0100] The terms "plants" and / or "target crops" are to be understood as also including 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 Clearfield®. 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 corn varieties, which are available in Roundup Ready 、Herculex I and LibertyLink Commercially available under the trade name ANTIQUID®.

[0101] The terms "plants" and / or "target crops" are to be understood as including those that are naturally or have been rendered resistant to harmful insects. This includes plants that have been transformed using recombinant DNA technology so as to, for example, synthesize one or more selectively acting toxins, such as are known from, for example, toxin-producing bacteria. Examples of toxins that may be expressed include delta-endotoxins, vegetative insecticidal proteins (Vips), insecticidal proteins of bacterial colonizing nematodes, and toxins produced by scorpions, arachnids, wasps and fungi. Examples of crops that have been modified to express Bacillus thuringiensis toxins are Bt maizeKnockOut (Syngenta Seeds). An example of a crop that includes more than one gene encoding insecticide resistance and thereby expresses more than one toxin is VipCot (Syngenta Seeds). Crops or their seed material may also be resistant to multiple types of pests (so-called stacked transgenic events when produced by genetic modification). For example, a plant may have the ability to express an insecticidal protein while being tolerant to a herbicide, such as Herculex I (Dow AgroSciences, Pioneer Hi-Bred International).

[0102] The term "plants" and / or "target crops" is to be understood as also including plants which have been transformed by the use of recombinant DNA techniques so that they can synthesize selectively active antipathogenic substances, 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 which 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 the person skilled in the art and are described, for example, in the publications mentioned above.

[0103] Toxins that can be expressed by transgenic plants include, for example, insecticidal proteins from Bacillus cereus or Bacillus japonicus; or insecticidal proteins from Bacillus thuringiensis, such as delta-endotoxins, for example Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, or Cry9C, or vegetative insecticidal proteins (Vips), for example Vip1, Vip2, Vip3, or Vip3A; or insecticidal proteins of bacterial colonizing nematodes, for example Photorhabdus spp. or Xenorhabdus spp., such as Photorhabdus luminescens, Xenorhabdus nematophila, or Xenorhabdus spp. nematophilus); toxins produced by animals, such as scorpion toxins, spider toxins, bee toxins and other insect-specific neurotoxins; toxins produced by fungi, such as streptomycin, plant lectins, such as pea lectin, barley lectin or snowdrop lectin; lectins (agglutinin); protease inhibitors, such as trypsin inhibitor, silk proteinase inhibitor, potato glycoprotein, cystatin, papain inhibitor; ribosome inactivating protein (RIP), such as ricin, maize-RIP, abrin, luffa seed toxin protein, saponin protein or bryophyllin; steroid metabolizing enzymes, such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidase, ecdysone inhibitors, HMG-COA-reductase, ion channel blockers, such as sodium channel or calcium channel blockers, juvenile hormone esterase, diuretic hormone receptor, stilbene synthase, bibenzyl synthase, chitinase and glucanase.

[0104] Further, in the context of the present invention, delta-endotoxins (e.g., Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, or Cry9C) or vegetative insecticidal proteins (Vips) (e.g., Vip1, Vip2, Vip3, or Vip3A) are understood to include, obviously, mixed toxins, truncated toxins, and modified toxins. Mixed toxins are recombinantly produced by new combinations of different domains of those proteins (see, e.g., WO 02 / 15701). Truncated toxins, such as truncated Cry1Ab, are known. In the case of modified toxins, one or more amino acids of the naturally occurring toxin are replaced. In such amino acid replacements, it is preferred that non-naturally occurring protease recognition sequences are inserted into the toxin, such as, for example, in the case of Cry3A055, the cathepsin-G-recognition sequence is inserted into the Cry3A toxin (see WO 03 / 018810).

[0105] Further examples of such toxins or transgenic plants capable of synthesizing such toxins are disclosed in, for example, EP-A-0 374 753, WO 93 / 07278, WO 95 / 34656, EP-A-0 427 529, EP-A-451 878 and WO 03 / 052073.

[0106] Methods for preparing such transgenic plants are generally known to the person skilled in the art and are described, for example, in the publications mentioned above. CryI-type deoxyribonucleic acids and their preparation are known, for example, from WO 95 / 34656, EP-A-0 367474, EP-A-0 401 979 and WO 90 / 13651.

[0107] The toxins contained in the transgenic plants render the plants tolerant to harmful insects. Such insects can be found in any insect taxonomic group, but are particularly common among beetles (Coleoptera), two-winged insects (Diptera), and moths (Lepidoptera).

[0108] Transgenic plants comprising one or more genes encoding insecticide resistance and expressing one or more toxins are known and some of them are commercially available. Examples of such plants are: YieldGard (corn variety expressing Cry1Ab toxin); YieldGard Rootworm (corn variety expressing Cry3Bb1 toxin); YieldGard Plus (corn variety expressing Cry1Ab and Cry3Bb1 toxins); Starlink (corn variety expressing Cry9C toxin); Herculex I (corn variety expressing the Cry1Fa2 toxin and the enzyme phosphinothricin N-acetyltransferase (PAT) that confers tolerance to the herbicide glufosinate-ammonium); NuCOTN 33B (cotton variety expressing Cry1Ac toxin); Bollgard I (cotton variety expressing Cry1Ac toxin); Bollgard II (cotton variety expressing Cry1Ac and Cry2Ab toxins); VipCot (cotton variety expressing Vip3A and Cry1Ab toxins); NewLeaf (potato variety expressing Cry3A toxin); NatureGard 、Agrisure GT Advantage (GA21 glyphosate tolerance trait), Agrisure CB Advantage (Bt11 corn borer (CB) trait) and Protecta .

[0109] Further examples of such genetically modified crops are:

[0110] 1. Bt11 corn, from Syngenta Seeds SAS, Chemin del'Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Genetically modified maize, which is resistant to attack by European corn borer (Ostrinia nubilalis and Sesamia inermis) by transgenic expression of a truncated Cry1Ab toxin. Bt11 corn also transgenic expression of the PAT enzyme to obtain tolerance to the herbicide glufosinate ammonium.

[0111] 2. Bt176 corn, from Syngenta Seeds, 27 Hobbit Road, F-31 790 Saint-Sauveur, France, registration number C / FR / 96 / 05 / 10. Genetically modified maize, which is resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia inermis) by transgenic expression of the Cry1Ab toxin. Bt176 corn also transgenic expression of the enzyme PAT to obtain tolerance to the herbicide glufosinate ammonium.

[0112] 3. MIR604 corn, from Syngenta Seeds, 27 Rue Hobbitt, F-31 790 Saint-Sauveur, France, registration number C / FR / 96 / 05 / 10. Corn rendered insect resistant by transgenic expression of a modified Cry3A toxin. This toxin is Cry3A055 modified by insertion of a cathepsin-G-protease recognition sequence. The preparation of such transgenic corn plants is described in WO 03 / 018810.

[0113] 4. MON 863 maize, from Monsanto Europe SA, 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / DE / 02 / 9. MON 863 expresses the Cry3Bb1 toxin and is resistant to certain coleopteran insects.

[0114] 5. IPC 531 Cotton, from Monsanto Europe AB, 270-272 Avenue Tervuren, B-1150 Brussels, Belgium, registration number C / ES / 96 / 02.

[0115] 6.1507 Maize, from Pioneer Overseas Corporation, Avenue Tedesco, 7B-1160 Brussels, Belgium, registration number C / NL / 00 / 10. Genetically modified maize expressing the protein Cry1F for resistance to certain lepidopteran insects and the protein PAT for tolerance to the herbicide glufosinate.

[0116] 7. NK603×MON 810 maize, from Monsanto Europe 270-272 Boulevard Tervuren, B-1150 Brussels, Belgium, registration number C / GB / 02 / M3 / 03. It is a conventionally bred hybrid maize variety, formed by crossing the genetically modified varieties NK603 and MON 810. NK603×MON 810 maize transgenically expresses the protein CP4 EPSPS obtained from the Agrobacterium strain CP4, which confers resistance to the herbicide Roundup The strain also expresses the Cry1Ab toxin from Bacillus thuringiensis subsp. kurstakia, which confers tolerance to certain lepidopteran insects, including the European corn borer.

[0117] As used herein, the term "locus" means a place where or on which plants grow, or where seeds of cultivated plants are sown, or where seeds are to be placed in the soil. It includes soil, seeds, and seedlings, together with established vegetation.

[0118] The term "plant" refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, leaves and fruits.

[0119] The term "plant propagation material" is understood to mean the reproductive parts of plants, such as seeds (which can be used for the propagation of plants), and vegetative materials, such as cuttings or tubers (e.g. potatoes). For example, seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes and parts of plants may be mentioned. Germinated plants and young plants that will be transplanted after germination or after emergence may also be mentioned. These young plants may be treated completely or partially by dipping and protected before transplanting. Preferably, "plant propagation material" is understood to mean seeds.

[0120] Pesticides referred to herein using their common names are known, for example, from “The Pesticide Manual”, 15th edition, British Crop Protection Council 2009.

[0121] The compound for use in the method of the present invention as defined in any one of Examples 1 to 6 can be the sole active ingredient of the composition, or it can be mixed with one or more additional active ingredients (such as pesticides, fungicides, synergists, herbicides or plant growth regulators) as appropriate. In some cases, the additional active ingredients can produce unexpected synergistic activity.

[0122] The compositions according to the invention may also contain further solid or liquid adjuvants, such as stabilizers, for example non-epoxidized or epoxidized vegetable oils (for example epoxidized coconut oil, rapeseed oil or soybean oil), defoamers (for example silicone oils), preservatives, viscosity regulators, adhesives and / or tackifiers, fertilizers or other active ingredients for obtaining specific effects, such as bactericides, fungicides, nematicides, plant activators, molluscicides or herbicides.

[0123] The compositions according to the invention are prepared in a manner known per se, in the absence of auxiliaries, for example by grinding, screening and / or compressing the solid active ingredient; and in the presence of at least one auxiliary, for example by intimately mixing the active ingredient with one or more auxiliary agents and / or grinding the active ingredient with one or more auxiliary agents. These methods for preparing the compositions and the use of compound (I) for preparing these compositions are also the subject matter of the present invention.

[0124] Another aspect of the present invention relates to the use of a compound as defined in Example 1, a composition comprising at least one compound as defined, or a fungicidal or insecticidal mixture comprising a compound as defined in Example 1, mixed with other fungicides or insecticides as described above, for controlling or preventing infestation of plants (e.g. plants (e.g. crop plants)), their propagation materials (e.g. seeds), harvested crops (e.g. harvested food crops), or non-living materials by insects or phytopathogenic microorganisms (preferably fungal organisms).

[0125] Another aspect of the present invention relates to a method for controlling or preventing plants (e.g. plants (e.g. crop plants)), their propagation materials (e.g. seeds), harvested crops (e.g. harvested food crops), or non-living materials from being infested by phytopathogenic microorganisms or spoilage microorganisms or organisms potentially harmful to humans (especially fungal organisms), which method comprises applying a compound as defined in Example 1 as an active ingredient to these plants, parts of these plants or their loci, their propagation materials, or any part of these non-living materials.

[0126] Control or prevention means the reduction of infestation by insects or phytopathogenic or spoilage microorganisms or organisms potentially harmful to humans, especially fungal organisms, to such a level that an improvement is demonstrated.

[0127] The preferred method of controlling or preventing crop plants from being infected by plant pathogenic microorganisms (especially fungal organisms) or insects is leaf application, which includes applying the compound as defined in Example 1 or an agrochemical composition containing at least one of the compound. Frequency of application and application ratio will depend on the risk of infection by the corresponding pathogen or insect. However, the compound with formula (I) can also be applied to the soil (soil application) by the soil through the root (systemic effect) penetration plant by the liquid formulation irrigating the place of the plant or by the compound in solid form, for example, in the form of particles, applied to the soil. In rice crops, such particles can be applied to the paddy field of irrigation. The compound with formula (I) can also be applied to the seed (coating) by dipping the seed or tuber with the liquid formulation of the fungicide or coating it with a solid formulation.

[0128] However, compounds of formula (I), preferably in combination with compound (B), can also penetrate the plant via the soil through the roots (systemic action) by flooding the locus of the plant with a liquid formulation or by applying the compound in solid form, for example in granular form, to the soil (soil application). In rice crops, such granules can be applied to flooded paddies. Compounds of formula (I) can also be applied to seeds (coating) by impregnating seeds or tubers with a liquid formulation of the fungicide or coating them with a solid formulation.

[0129] Further features of the preferred dual compositions comprising the compound of formula (I), the methods of applying them to cereals and their use rates are as described for the compositions comprising the compound of formula (I) and additionally preferably at least one component (B) as described above.

[0130] Their application can be before and after these plants or their parts are infected by fungi.Preferably, before infection, process.When the compound with formula (I) is used by itself, the application ratio according to the method of the present invention is as described above, for example, typically 5 to 2000g ai / ha, particularly 10 to 1000g ai / ha, for example the ratio of 50g ai. / ha, 75g ai / ha, 100g ai / ha or 200g ai / ha.During the growth period, the compound with formula (I) can be applied to these plants once or more than once.

[0131] For use in the process according to the 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 use form will depend on the specific intended purpose; in each case, it should ensure a fine and uniform distribution of the compound of formula (I).

[0132] The term "plants" as used herein includes seedlings, shrubs and crops of fruits and vegetables.

[0133] The following examples are used to illustrate the present invention, "active ingredient" means a mixture of component (A) and component (B) in a specific mixing ratio. The same formulation can be used in a composition containing only the compound of formula (I) as the active ingredient.

[0134] The invention will now be illustrated by the following non-limiting examples.All references cited are incorporated by reference.

[0135] Preparation Examples

[0136]

[0137] The active ingredient is mixed thoroughly 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.

[0138]

[0139] 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.

[0140] Emulsifiable concentrates

[0141]

[0142] Emulsions of any desired dilution which can be used in plant protection can be obtained from these concentrates by dilution with water.

[0143]

[0144] 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 of seeds.

[0145]

[0146] 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.

[0147] Suspension concentrates

[0148]

[0149]

[0150] 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 a dilution, living plants as well as plant propagation materials can be treated and protected against microbial infestation by spraying, pouring or immersion.

[0151] Flowable concentrate for seed treatment

[0152]

[0153] The finely ground active ingredient is thoroughly mixed with other formulation components to obtain a suspension concentrate, which can be further diluted in water for application to seeds. Using such dilutions, propagation materials can be treated and protected from microbial infestation by spraying, pouring or dipping.

[0154] Biological Examples

[0155] experiment:

[0156] Compound: 2-[2-(7,8-difluoro-2-methylquinolin-3-yloxy)-6-fluorophenyl]propan-2-ol

[0157]

[0158] Example 1: Coryneformis multifiliis (target leaf spot)

[0159] The fungus conidia from frozen storage is directly mixed in the nutrient broth (PDB potato dextrose broth). The DMSO solution of the test compound is placed in a microtiter plate (96-well specification) and the nutrient broth containing the fungus spore is added thereto. These test plates are incubated at 24 ℃ and after 3-4 days at 620nm photometrically determined to the inhibition of growth (% control of polyprimary coryneformis). The activity of the compound is drawn by comparing the inhibition of growth in the treated test solution with the growth in the untreated control. The concentration of the compound is 6.7, 2.2, 0.74, 0.25 and 0.082ppm.

[0160] When compared to untreated controls that showed extensive disease development under the same conditions, 2-[2-(7,8-difluoro-2-methylquinolin-3-yloxy)-6-fluorophenyl]propan-2-ol gave at least 90% control of Psoralea corylifolia at 6.7 ppm, at least 70% control of Psoralea corylifolia at 2.2 ppm, at least 50% control at 0.74 ppm, and at least 20% at 0.25 and 0.027 ppm.

[0161] Example 2: Gray leaf spot pathogen (soybean gray leaf spot):

[0162] Fungal conidia from frozen storage were mixed directly 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 the inhibition of growth was determined photometrically at 620nm after 3-4 days.

[0163] 2-[2-(7,8-difluoro-2-methylquinolin-3-yloxy)-6-fluorophenyl]propan-2-ol gave at least 50% control of Gray Leaf Spot Pseudomonas aeruginosa at 6.7 and 2.2 ppm, and at least 20% control at 0.74 and 0.25 ppm, when compared to untreated controls which showed extensive disease development under the same conditions.

[0164] Example 3: Soybean purple spot pathogen (leaf blight):

[0165] Fungal conidia from frozen storage were mixed directly 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 the inhibition of growth was determined photometrically at 620nm after 3-4 days.

[0166] 2-[2-(7,8-difluoro-2-methylquinolin-3-yloxy)-6-fluorophenyl]propan-2-ol gave at least 50% control of Gray Leaf Spot Pseudomonas aeruginosa at 6.7 and 2.2 ppm, and at least 20% control at 0.74 ppm, when compared to untreated controls which showed extensive disease development under the same conditions.

[0167] Thus, 2-[2-(7,8-difluoro-2-methylquinolin-3-yloxy)-6-fluorophenyl]propan-2-ol can be distinguished from other compounds, for example, by a greater efficacy against Pseudomonas multilocus, Gray Spot Pathogen and / or Pseudomonas aeruginosa, alone or in combination at low application rates, which can be confirmed by a person skilled in the art using the experimental procedures outlined in the biological tests above, using lower application rates (if necessary), for example 6 ppm, 3 ppm, 2.2 ppm, 1.5 ppm, 0.8 ppm, 0.74 ppm, 0.25 ppm, 0.2 ppm, or 0.082 ppm.

Claims

1. A method for controlling or preventing plants from being infected by the plant pathogenic microorganism Coryneformis, the method comprising applying a fungicidally effective amount of 2-[2-(7,8-difluoro-2-methylquinolin-3-yloxy)-6-fluorophenyl]propan-2-ol or a salt thereof to the plant pathogen, the site of the plant pathogen, or a plant susceptible to attack by the plant pathogen, or its propagation material.

2. The method according to claim 1, comprising the steps of: A composition comprising a biocidally effective amount of 2-[2-(7,8-difluoro-2-methylquinolin-3-yloxy)-6-fluorophenyl]propan-2-ol is provided; and applying the composition to a propagation material; and planting the propagation material.

3. The method according to claim 1, comprising the steps of: Provided are a composition comprising a biocidally effective amount of 2-[2-(7,8-difluoro-2-methylquinolin-3-yloxy)-6-fluorophenyl]propan-2-ol; and applying the composition to the plant pathogen, the locus of the plant pathogen, or a plant susceptible to attack by the plant pathogen.

4. The method according to any one of claims 1 to 3, wherein: The plant is selected from cowpea, cucumber, papaya, soybean, sweet potato, tomato, cotton, eggplant, basil, thyme, rubber tree, pawpaw tree, azalea and hydrangea.

5. The method according to claim 4, wherein: The plant is selected from the group consisting of cowpea, cucumber, papaya, soybean, sweet potato and tomato.

6. The method according to claim 5, wherein: The plant is soybean.

7. A method for controlling or preventing plants from being infected by the plant pathogenic microorganism Coryneformis, the method comprising applying an agricultural composition to the plant pathogen, the site of the plant pathogen, or a plant susceptible to attack by the plant pathogen, or its propagation material, the agricultural composition comprising a fungicidally effective amount of 2-[2-(7,8-difluoro-2-methylquinolin-3-yloxy)-6-fluorophenyl]propan-2-ol or a salt thereof as an active ingredient, and at least one or more other biologically active agents, one or more adjuvants, and a diluent or carrier.

8. The method according to claim 7, wherein the agricultural composition comprises (A) a fungicidally effective amount of 2-[2-(7,8-difluoro-2-methylquinolin-3-yloxy)-6-fluorophenyl]propan-2-ol or a salt thereof as a first active ingredient; and (B) at least one second active ingredient selected from the group consisting of: 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol; 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol; 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxy-propyl]imidazole. oxadiazole-4-carbonitrile; 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile; (4-phenoxyphenyl)methyl 2-amino-6-methyl-pyridine-3-carboxylate; 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetraone; N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiobenzamide; N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide; (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methyl Oxyimino-N,3-dimethyl-pent-3-enamine; N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine; N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine; 2-(difluoromethyl)-N-[(3S)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide; 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridinyl]-1-(1,2,4-triazol-1-yl)propan-2-ol; 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thio-4H-1,2,4-triazol-1-yl)propan-2-ol [(2-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl]acetamide; N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzonitrile; N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine; N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine; N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiobenzamide; 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide; N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide; syringoxystrobin, zhongshengmycin, thiophanate-copper, thiazole zinc, amitoline, iprodione;Fluxaprolin, enoxamyl; trinexapac-ethyl; syringystrobin; syringystrobin; (4-phenoxyphenyl)methyl 2-amino-6-methyl-pyridine-3-carboxylate; N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiobenzamide; N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide; (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide; N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine; 3-[2-(1-chlorocyclopropyl)-3 -(2-Fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile; 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile; 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide; (E)-3-methoxy-2-[2-[(5-methoxy-1,3-benzothiazol-2-yl)sulfanylmethyl]phenyl]prop-2-enoic acid methyl ester; 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile; 4-[[6-[2-(2,4-difluorophenyl)- 1,1-Difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile; 3-(3,4-dichloro-1,2-thiazol-5-ylmethoxy)-1,2-benzothiazole 1,1-dioxide; (2E)-2-{2-[({[(2E,3E)-4-(4-chlorophenyl)but-3-en-2-ylidene]-amino}oxy)methyl]phenyl}-3-methoxyprop-2-enoic acid methyl ester; 2Z)-2-[2-[[(E)-[(E)-4-(2,6-dichlorophenyl)but-3-en-2-ylidene]amino]oxymethyl]phenyl]-2-methoxyimino-N-methylacetamide; (3S,6S,7R,8R )-8-benzyl-3-{3-[(isobutyryloxy)methoxy]-4-methoxypyridine-2-carboxamido}-6-methyl-4,9-dioxo-1,5-dioxacyclononan-7-yl isobutyrate; [(1S)-2,2-bis(4-fluorophenyl)-1-methyl-ethyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate; 3-(difluoromethyl)-N-[(3RS)-7-fluoro-2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide; 3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide;(2RS)-2-[4-(4-chlorophenoxy)-α,α,α-trifluoro-o-tolyl]-3-methyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol; 2-[2-[(7,8-difluoro-2-methyl-3-quinolyl)oxy]-6-fluoro-phenyl]propan-2-ol; 2-[2-[(2,5-dimethylphenoxy)methyl]phenyl]-2-methoxy-N-methyl 1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazolyl-5-one; N-[2-[(2,4-dimethyl-5-phenylpyrazol-3-yl] (E)-2-[2-[[5-(4-chlorophenyl)-2-methylpyrazol-3-yl]oxymethyl]phenyl]-3-methoxyprop-2-enoic acid methyl ester; (Z)-N-{2-[3-chloro-5-(cyclopropylethynyl)-2-pyridinyl]-2-(isopropoxyimino)ethyl}-3-(difluoromethyl)-1-methylpyrazol-4-yl -carboxamide; N-methoxy-N-[2-[(3,5,6-trichloropyridin-2-yl)oxymethyl]phenyl]carbamic acid methyl ester; N-[2-[2,4-dichloro-phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide; N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]-phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide;N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl ] urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]-methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-isoxazolidin-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-isoxazolidin-3-one, 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-yl -ethyl formate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-1,2,4-triazol-3-amine; 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine, N'-[2-chloro-4-(2-fluorophenoxy)- 2-(4-(trifluoromethyl)-5-methyl-phenyl)-N-ethyl-N-methyl-formamidine, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiobenzamide, 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide and N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide; (4-phenoxyphenyl)methyl 2-amino-6-methyl-pyridine-3-carboxylate; 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetraone;N-Methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiobenzamide; N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide; (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide; N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine; N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine; N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-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; 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile; 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-propyl]imidazole-4 -carbonitrile; 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide; (E)-3-methoxy-2-[2-[(5-methoxy-1,3-benzothiazol-2-yl)sulfanylmethyl]phenyl]prop-2-enoic acid methyl ester; 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridinyl]oxy]benzonitrile; 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3-pyridinyl]oxy]benzonitrile; 3-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3-pyridinyl]oxy]benzonitrile; -(3,4-dichloro-1,2-thiazol-5-ylmethoxy)-1,2-benzothiazole 1,1-dioxide; (3S,6S,7R,8R)-8-benzyl-3-{3-[(isobutyryloxy)methoxy]-4-methoxypyridine-2-carboxamido}-6-methyl-4,9-dioxo-1,5-dioxacyclononan-7-yl isobutyrate; [(1S)-2,2-bis(4-fluorophenyl)-1-methyl-ethyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate; 3-(difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl-indan-4-yl)-1-methyl-pyrazole-4-carboxamide;[2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]thiazol-4-yl]-4,5-dihydroisoxazol-5-yl]-3-chloro-phenyl] methanesulfonate; 3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide; (2RS)-2-[4-(4-chlorophenoxy)-α,α,α-trifluoro-o-tolyl]-3-methyl-1-(1H-1,2,4-triazol-1-yl)butyl- 2-ol; 2-[2-[(7,8-difluoro-2-methyl-3-quinolyl)oxy]-6-fluoro-phenyl]propan-2-ol; N-[1,1-dimethyl-2-(4-isopropoxy-o-tolyl)-2-oxoethyl]-3-methylthiophene-2-carboxamide; N-[(5-chloro-2-isopropyl-phenyl)methyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-pyrazole-4-carboxamide; 2-[2-[(2,5-dimethylphenoxy)methyl]phenyl]-2-methoxy-N-methyl-acetamide; (2RS)-2-[4-(4-chlorophenoxy)-α,α,α-trifluoro-o-tolyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol; 1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one; (Z)-N-{2-[3-chloro-5-(cyclopropylethynyl)-2-pyridinyl]-2-(isopropoxyimino)ethyl}-3-(difluoromethyl)-1-methylpyrazole-4-carboxamide; N-[2-(3,4 -difluorophenyl)phenyl]-3-(trifluoromethyl)pyrazine-2-carboxamide; 3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine; 3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1-yl)quinoline; N-[2-[2,4-dichloro-phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide; and / or N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide;2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridinyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3-pyridinyl]oxy]benzonitrile, N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine, N'-[2- Chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiobenzamide, 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide and N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, or a combination thereof. ; 9. The method according to claim 8, wherein the agricultural composition comprises from 0.01% to 90% by weight of the active ingredients (A) and (B), and from 0% to 20% by weight of an agriculturally acceptable surfactant.

10. The method of claim 9, wherein the agricultural composition comprises a concentrate composition for dilution by a user, comprising an agricultural composition according to claim 8 or 9, comprising from 2 to 80% by weight of active ingredients (A) and (B).

11. Use of a fungicidally effective amount of 2-[2-(7,8-difluoro-2-methylquinolin-3-yloxy)-6-fluorophenyl]propan-2-ol or a salt thereof for controlling or preventing plants from being infected by the plant pathogenic microorganism Corynespora polytomata.

12. The use according to claim 11, wherein a fungicidally effective amount of 2-[2-(7,8-difluoro-2-methylquinolin-3-yloxy)-6-fluorophenyl]propan-2-ol or a salt thereof is used in combination with the compound (B) defined in claim 8.

13. The method according to any one of claims 1 to 3, wherein: The plant is a legume.

Images