fungicidal composition

Abstract

Disclosed is an antifungal composition comprising a mixture of components (A) and (B), wherein components (A) and (B) are as defined in claim 1, and the use of said composition in agriculture or horticulture for controlling or preventing plant infection by plant pathogenic microorganisms, preferably fungi.

Description

[0001] This application is a divisional application of Chinese Patent Application No. 202180018462.4 entitled "Antifungal Composition", which was filed on March 5, 2021, and has the earliest priority date of March 5, 2020.

[0002] This invention relates to novel antifungal compositions, their use in agriculture or horticulture for controlling diseases caused by plant pathogens (especially plant pathogenic fungi), and methods for controlling diseases on beneficial plants.

[0003] Although many fungicidal compounds and compositions belonging to various chemical classes have been developed or are being developed for use as fungicides in beneficial plant crops, crop tolerance and activity against specific plant pathogens do not always meet the needs of agricultural practice in many respects. Therefore, there is a persistent need to discover new compounds and compositions with superior biological properties for the control or prevention of plant infection by plant pathogens. For example, compounds with greater biological activity, favorable activity spectra, increased safety, improved physicochemical properties, or increased biodegradability; or, alternatively, compositions with broader activity spectra, improved crop tolerance, improved synergistic interactions or enhancing properties, or compositions exhibiting faster onset of action or longer residual activity, or compositions that reduce the number of applications and / or application rate required for effective control of plant pathogens, thereby enabling beneficial tolerance management practices, reducing environmental impact, and reducing operator exposure.

[0004] Some of these needs can be addressed by using compositions containing mixtures of different fungicidal compounds with different modes of action (e.g., by combining fungicides with different activity spectra).

[0005] According to the present invention, an antifungal composition is provided comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is a compound having formula (I).

[0006]

[0007] in

[0008] R 1 It is methyl;

[0009] R 2 It is hydrogen;

[0010] R 3 It is hydrogen;

[0011] R 4 It is a C3-C7 cycloalkyl group;

[0012] Or its agronomically acceptable salt;

[0013] and

[0014] Component (B) is a compound selected from the group consisting of:

[0015] Bifenazate, sulfur, copper hydroxide, chlorpyrifos, acibenzolar-S-methyl, copper oxychloride, cyclohexidine, difenoconazole, flutriafol, fenpyroximate, hexaconazole, tebuconazole, thiophanate-methyl, prochloraz, imazalil, propiconazole, azoxystrobin, tebuconazole, fenpropidin, butyl morpholine, spirocyclam, pyraclostrobin, fludioxonil, metalaxyl, metalaxyl-M (metalaxyl-M), carbendazim, penthiophanate-methyl, azoxystrobin, pyraclostrobin, fenpyroximate, fenpyroximate, fenpyroximate, fluazinam, fluazinam, fenpyroximate, fenpyroximate, fenpyroximate, fenpyroximate, fenpyroximate, fenpyroximate, mancozeb, captan, chlorothalonil, fluazinam, fluazinam Cyclopyralid, Fosetyl-aluminium, Pyrafenib, Tricyclazole, Mandipropamid, Flufenoxuron, Isopyrazam, Sedaxane, Benzoflufenazole, Fluopyram, Isoflavone, Dipymetitrone, Fluindapyr, Jiaxiangjunzhi, Lvbenmixianan, Mandespin obin, oxathiapiprolin, piraziflumid, inpyrfluxam, chlorfluazuron, ipfentrifluconazole, aminopyrifen, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, pyridoxamid, fenpicoxamid, ipflufenoquin, quinofolin Inofumelin), benomyl, fluopyram, pyrapropoyne, 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, metyltetraprole, fluoxapiprolin, enoxastrobin, 4-[[6-[2-(2,4-difluorophenyl)-1,1-Difluoro-2-hydroxy-3-(5-thio-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, trinexapac, trinexapac ester, eugenol, N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methylformamidinium, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methylformamidinium, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methylformamidinium, N'-[5- [Chloro-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methylformamidin, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methylformamidin, N'-[5-bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N-methylformamidin, N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenyl-ethyl)phenyl]-N-methylformamidin, N'-[4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-methoxy-2-methyl-phenyl] -N-Isopropyl-N-methylformamidinium, N-ethyl-N'-[5-methoxy-2-methyl-4-[2-trifluoromethyl)oxetane-2-yl]phenyl]-N-methylformamidinium, N-ethyl-N'-[5-methoxy-2-methyl-4-[2-trifluoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methylformamidinium, N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropaneformamide, N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide [4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide, [(1S,2S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(4-methoxy-3-propionyloxy-pyridine-2-carbonyl)amino]propionate, 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]urea4-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]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidine-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]pyrazole-4-carboxylic acid ethyl ester, [[3-triazolyl]phenyl]methyl]-1,2,4-triazolyl-3-amine, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)prop-2-ol, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)prop-2-ol, 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazol-4-carboxylon, 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]imidazol-4-carboxylon, methyl 2-amino-6-methylpyridine-3-carboxylic acid (4-phenoxyphenyl) 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; (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl] ketone; (3-methylisooxazol-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl] ketone; 1-[[5-[5-(trifluoromethyl)-1, 2,4-Oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylic acid ethyl ester, 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide, N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, N-[N-methoxy-C-methyl-carbonimino]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, N-[3-(4-chlorophenyl)-4,5-dihydroisoxazol-5-yl]-5-methyl-1,2,4-oxadiazol-3-carboxamide, 2-(difluoromethyl)-N-(1,1-Dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide, [(1S,2S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propionate, [(1S,2S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl](2S)-2-[[3-(acetoxymethoxy)-4-methoxy-pyridine-2-carbonyl]amino]propionate, cis-jasmone, potassium phosphonate, calcium phosphonate, glyphosate (including its diammonium, isopropylammonium and potassium salts), 2,4-D (including its choline salts and 2-ethylhexyl esters), dicamba (including its aluminum, aminopropyl, and bis-aminopropylmethyl) The following substances are listed: acetyl, choline, 1,3-dichloropropene, diethylene glycolamine, dimethylamine, dimethylammonium, potassium and sodium salts), glufosinate (including its ammonium salts), thiamethoxam, cyclobutrifluram, isoxaflutamide, spiropidion, abamectin, emamectin, brofenoxam, chlorantraniliprole, buprofen, broflanilide, 2-chloro-N-cyclopropyl-5-(1-{2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-1H-pyrazol-4-yl)-N-methylnicotinamide, and fluxametamide.

[0016] Typically, the weight ratio of component (A) to component (B) can preferably be from 100:1 to 1:100, from 50:1 to 1:50, from 20:1 to 1:50, from 15:1 to 1:50, from 15:1 to 1:30, from 12:1 to 1:25, from 10:1 to 1:20, from 5:1 and 1:15, from 3:1 to 1:10, or from 2:1 to 1:5.

[0017] In addition, according to the present invention, a method for controlling or preventing plant pathogenic diseases, especially plant pathogenic fungi, on useful plants or their propagation material is provided, the method comprising applying a fungicidal composition according to the present invention to such useful plants, their sites or their propagation material.

[0018] The benefits provided by certain fungicidal mixture compositions according to the invention may also include, in particular, favorable levels of bioactivity for protecting plants against fungal diseases or superior properties for use as an agrochemical active ingredient (e.g., greater bioactivity, favorable activity spectrum, increased safety, improved physicochemical properties, or increased biodegradability).

[0019] For compounds having formula (I) with substituent R 1 R2 R 3 and R 4 The preferred groups and values, and any combination thereof, are listed below.

[0020] R 1 It is a methyl group.

[0021] R 2 It's hydrogen.

[0022] R 3 It's hydrogen.

[0023] R 4 It is a C3-C7 cycloalkyl group.

[0024] Preferably, component (A) is a compound selected from the following:

[0025] (Z)-2-(5-cyclobutyl-2-methylphenoxy)-3-methoxy-prop-2-enoic acid methyl ester

[0026] (Compound X.01),

[0027] (Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxy-prop-2-enoic acid methyl ester

[0028] (Compound X.02),

[0029] (Z)-2-(5-cyclopropyl-2-methylphenoxy)-3-methoxy-prop-2-enoic acid methyl ester

[0030] (Compound X.03), or

[0031] (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxy-prop-2-enoic acid methyl ester

[0032] (Compound X.04), as defined in Table X below.

[0033] More preferably, component (A) is a compound selected from the following:

[0034] (Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxy-prop-2-enoic acid methyl ester

[0035] (Compound X.02), or

[0036] (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxy-prop-2-enoic acid methyl ester

[0037] (Compound X.04), as defined in Table X below.

[0038] In one embodiment, component (A) is (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester (compound X.02).

[0039] In another embodiment, component (A) is (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester (compound X.04).

[0040] Table X

[0041]

[0042]

[0043] Component (B) is a compound selected from the group consisting of:

[0044] Bifenthion, sulfur, copper hydroxide, chlorpyrifos, aramid-benzene-S-methyl, copper oxychloride, cyclohexidine, difenoconazole, flutriafol, fenbendazole, hexaconazole, styraconazole, tebuconazole, paclobutrazol, prothioconazole, imazalil, propiconazole, azoxystrobin, tebuconazole, benzyl benzoate, spirocyclohexidine, pyraclostrobin, fludioxonil, metalaxyl, metalaxyl-M (refined metalaxyl) (e.g., carbendazim, pyraclostrobin, azoxystrobin, fenpyroxime, cyclopyr, fluopyram, fluopyram, fenoxystrobin, cyclopyr, pyraclostrobin, pyraclostrobin, pyraclostrobin, mancozeb, captan, chlorothalonil, fluazinam, fluopyram, cyclopyr, aluminum trisphosphonate, pyraclostrobin, tricyclazole, dimethomorph, fludioxonamide, pyrazole) Naphthylamine, fluoxastrobin, benzylfluopyram, fluoxastrobin, isofluran, isothiazamide, difenoconazole, fluinazole, methylphenidate, Rubenmician, mandesbin, fluoxastrobin, bifenpyrazinamide, impetigosam, chlorfluazuron, isofentefluconazole, eminoprofen, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, pyridoxam, fenpicomide, flubendiquin, quinofolin, benzylfluopyram, flupyramide, pyrimethanil, 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide, 4-[[6-[2-(2,4-di-di-] 1,1-Difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, Meteltetrapro, fluoperidine, acetamiprid, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thio-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, anti-acid, anti-acid ester, eugenol, N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methylformamidinium, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3 [-pyridyl]-N-ethyl-N-methylformamidinium, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methylformamidinium, N'-[5-chloro-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methylformamidinium, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methylformamidinium, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methylformamidinium, N'-[5-bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N-methylformamidinium, N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-Trifluoro-1-hydroxy-1-phenyl-ethyl)phenyl]-N-methylformamidinium, N'-[4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-methoxy-2-methyl-phenyl]-N-isopropyl-N-methylformamidinium, N-ethyl-N'-[5-methoxy-2-methyl-4-[2-trifluoromethyl)oxetane-2-yl]phenyl]-N-methylformamidinium, N-ethyl-N'-[5-methoxy-2-methyl-4-[2-trifluoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methylformamidinium, N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzoyl Amines, 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, [(1S,2S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(4-methoxy-3-propionyloxy-pyridine-2-carbonyl)amino]propionate, 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]isoxazolidine-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, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)prop-2-ol, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)prop-2-ol]4-Triazol-1-yl)prop-2-ol, 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazol-4-carboxylon, 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]imidazol-4-carboxylon, methyl 2-amino-6-methylpyridine-3-carboxylic acid (4-phenoxyphenyl) ester, 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 5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl] ketone, (3-methylisoxazol-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl] ketone, 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylic acid ethyl ester, 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide, N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, N -[N-methoxy-C-methyl-carboimide]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, N-[3-(4-chlorophenyl)-4,5-dihydroisoxazol-5-yl]-5-methyl-1,2,4-oxadiazol-3-carboxamide, 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide, [(1S,2S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propionate, [(1S,2S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl] (2S)-2-[[3-(acetoxymethoxy)-4-methoxy-pyridine-2-carbonyl]amino]propionate, cis-jasmone, potassium phosphonate, calcium phosphonate, glyphosate (including its diammonium, isopropylammonium and potassium salts), 2,4-D (including its choline salt and 2-ethylhexyl ester), dicamba (including its aluminum, aminopropyl, bis-aminopropylmethyl, choline, 1,3-dichloropropene, diethylene glycolamine, dimethylamine, dimethylammonium, potassium and sodium salts), glufosinate (including its ammonium salts), thiamethoxam, cycloflufenoxam, isoxaflutole, methoxypiperidine ethyl ester, abamectin, emamectin, brofenoxam, chlorantraniliprole, buprofen, brofenoxam, 2-chloro-N-cyclopropyl-5-(1-{2,6-dichloro-4-[1,2,2,2-Tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-1H-pyrazol-4-yl)-N-methylnicotinamide and fluoxazolamide.

[0045] Preferably, component (B) is a compound selected from the group consisting of: bifenthiophanate-methyl, sulfur, copper hydroxide, chlorpyrifos, aramid-benzene-S-methyl, copper oxychloride, cyclohexidine, difenoconazole, flutriafol, fenbendazole, hexaconazole, tebuconazole, paclobutrazol, prothioconazole, imazalil, propiconazole, pyraclostrobin, tebuconazole, benzyl benzoate, spirocycline, pyraclostrobin, fludioxonil, metalaxyl, metalaxyl-M (metalaxyl-M), carbendazim, pyraclostrobin Azoxystrobin, fenpyroxime, fenpyroxime, fluopyram, flupyraclostrobin, fenoxystrobin, fenpyroxime, fenpyroxime, fenpyroxime, fenpyroxime, fenpyroxime, mancozeb, captan, chlorothalonil, fluazinam, fluazinam, cyclophosphamide, aluminum tris(ethyl phosphonate), pyraclostrobin, tricyclazole, dimethomorph, fludioxonil, pyraclostrobin, fluazinam, benzo[a]fluoroquinolones, fluazinam, isoflurane, isothiazine, difenoconazole, fludioxonil, fluazinam Azoxystrobin, Rubenmicin, Mandespin, Fluoxetine, Bifenazate, Impetazom, Chlorfluazol, Isifenfloxacin, Eminoxetine, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, Pyridamole, Fenpicomide, Flubenzin, Quinofolin, Benzylpyridin, Fluopyram, Pyripropyn, 2-(difluoromethyl)-N- (3-Ethyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, metronidazole, fluoperidol, tebufenozide, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thio-4H-1,2,4-Triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, anti-cure acid, anti-cure ester, eugenol, N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidin, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidin, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidin, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidin, N'-[5-chloro-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl N-methyl-N-formamidinium, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidinium, N'-[5-bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidinium, N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenyl-ethyl)phenyl]-N-methyl-formamidinium, N'-[4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-methoxy-2-methyl-phenyl]-N-isopropyl-N-methyl-formamidinium, N-ethyl-N'-[5-methoxy-2-methyl-4 ... -[2-trifluoromethyl)oxetane-2-yl]phenyl]-N-methylformamidinium, N-ethyl-N'-[5-methoxy-2-methyl-4-[2-trifluoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methylformamidinium, N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropaneformamide, 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]isoxazolidine-3-one4-Oxadiazol-3-yl]phenyl]methyl]isoxazolidine-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, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)prop-2-ol, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)prop-2-ol, 3-[2-( 1-Chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazolium-4-carboxylon, 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]imidazolium-4-carboxylon, 2-amino-6-methyl-pyridine-3-carboxylic acid (4-phenoxyphenyl) methyl ester, 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, ( 5-Methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl] ketone, (3-methylisoxazol-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl] ketone, 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylic acid ethyl ester, 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide, N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, N- [N-methoxy-C-methyl-carbonimide]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, N-[3-(4-chlorophenyl)-4,5-dihydroisoxazol-5-yl]-5-methyl-1,2,4-oxadiazol-3-carboxamide, 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide, [(1S,2S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propionate, [(1S,2S)-2-(4-fluoro-2-methyl-phenyl)-1,3-Dimethyl-Butyl](2S)-2-[[3-(acetoxymethoxy)-4-methoxy-pyridine-2-carbonyl]amino]propionate, cis-jasmone, potassium phosphonate, calcium phosphonate, glyphosate (including its diammonium, isopropylammonium and potassium salts), 2,4-D (including its choline salt and 2-ethylhexyl ester), dicamba (including its aluminum, aminopropyl, bis-aminopropylmethyl, choline, 1,3-dichloropropene, diethylene glycolamine, dimethylamine, dimethyl... (Ammonium, potassium, and sodium salts), glufosinate (including its ammonium salts), thiamethoxam, cycloflufenicol, isoxaflutamide, methoxypiperidine ethyl ester, abamectin, emamectin, cyananthramide, chlorantraniliprole, buprofen, bromuconazole, 2-chloro-N-cyclopropyl-5-(1-{2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-1H-pyrazol-4-yl)-N-methylnicotinamide, and fluoxazolamide.

[0046] More preferably, component (B) is a compound selected from the group consisting of: bifenthiophanate-methyl, chlorpyrifos, cyclophosphamide, difenoconazole, flutriafol, fenpyroxacin, hexaconazole, tebuconazole, fenpyroxacin, propiconazole, propiconazole, tebuconazole, azoxystrobin, fenpyroxacin, oxadiazon, fenpyroxacin, fluopyram, fluopyram, fenpyroxacin, fenpyroxacin, fenpyroxacin, fenpyroxacin, fenpyroxacin, fenpyroxacin, mancozeb, chlorothalonil, fluopyram, pyraclostrobin, benzovindiflubenzuron, isoflurane, fenpyroxacin, mandestrobin, chlorpyrifos, ipfentrifluconazole zole, benzylthiamethoxam, metyltetraprole, enoxastrobin, eugenol, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)prop-2-ol, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)prop-2-ol, 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazol-4-carboxylon, and 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]imidazol-4-carboxylon.

[0047] Even more preferably, component (B) is a compound selected from the group consisting of: cyclohexane, difenoconazole, hexaconazole, prothioconazole, propiconazole, azoxystrobin, oxadiazon, azoxystrobin, pyraclostrobin, azoxystrobin, mancozeb, chlorothalonil, fluopyram, benzalkonium chloride, isoflurane, and metyltetraprole.

[0048] Even more preferably, component (B) is a compound selected from the group consisting of: cyclohexanil, difenoconazole, hexaconazole, prothioconazole, propiconazole, azoxystrobin, oxadiazon, pyraclostrobin, pyraclostrobin, pyraclostrobin, and metronidazole.

[0049] Furthermore, even more preferably, component (B) is a compound selected from the group consisting of: cyclohexane, difenoconazole, prothioconazole, azoxystrobin, oxadiazon, azoxystrobin, and metyltetraprole.

[0050] Furthermore, preferably, component (B) is pyraclostrobin or oxadiazon.

[0051] Most preferably, component (B) is azoxystrobin.

[0052] In one embodiment, component (B) is a compound selected from the group consisting of: cyclohexanil, difenoconazole, hexaconazole, prothioconazole, propiconazole, benzyl benzoate, butyl morpholine, fludioxonil, azoxystrobin, oxadiazon, pyraclostrobin, pyraclostrobin, azoxystrobin, mancozeb, captan, chlorothalonil, fluopyram, benzo[2]fluopyram, isoflurane, fluopyram, chlorfluazon, pyridaben, meteltetrapro, N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, and [(1S,2S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(4-methoxy-3-propionyloxy-pyridine-2-carbonyl)amino]propionate. Preferably, component (B) is a compound selected from the group consisting of: cyclohexanil, difenoconazole, prothioconazole, benzyl benzoate, buprofen, fludioxonil, azoxystrobin, oxadiazon, azoxystrobin, mancozeb, captan, chlorothalonil, benzo[a]fluopyram, fluopyram, chlorpyrifos, pyridabenamide, meteltetrapro, N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, and [(1S,2S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(4-methoxy-3-propionyloxy-pyridine-2-carbonyl)amino]propionate.

[0053] These component (B) compounds are referred to herein and above by their so-called "ISO common name" or another "common name" or trademark name, as used in individual cases. These component (B) compounds are known and commercially available and / or can be prepared using procedures known in the art and / or procedures reported in the literature.

[0054] In a preferred composition according to the invention, component (A) is methyl 2-(5-cyclobutyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate or a salt or tautomer thereof, and component (B) is a compound selected from the group consisting of: bifenthiophanate-methyl, chlorpyrifos, cyclophosphamide, difenoconazole, flutriafol, fenpyroxacin, hexaconazole, tebuconazole, thiophanate-methyl, propiconazole, and tebuconazole. Alcohol, azoxystrobin, fenpyroxime, enoxastrobin, fluopyram, flupyraclostrobin, fenoxystrobin, fenpyroxime, fenpyroxime, fenpyroxime, azoxystrobin, fenpyroxime, mancozeb, chlorothalonil, fluopyram, pyraclostrobin, benzalkonium chloride, isoflurane, jiaxiangjunzhi, mandestrobin, chlorfluazuron, ipfentrifluconazole, benomyl, metyltetraprole, enoxastrobin, eugenol, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)prop-2-ol, 2-[6-(4-bromophenoxy)-2- [(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)prop-2-ol, 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazol-4-carboxylon, and 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]imidazol-4-carboxylon, wherein the weight ratio of component (A) to component (B) is from 15:1 to 1:50.

[0055] In another preferred composition according to the invention, component (A) is methyl 2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate or a salt or tautomer thereof, and component (B) is a compound selected from the group consisting of: bifenthiophanate-methyl, chlorpyrifos, cyclophosphamide, difenoconazole, flutriafol, fenpyroxacin, hexaconazole, tebuconazole, thiophanate-methyl, propiconazole. Tebuconazole, azoxystrobin, fenpyroxime, tebuconazole, flufenoxuron, flupyraclostrobin, fenoxystrobin, fenpyroxime, fenpyroxime, fenpyroxime, azoxystrobin, fenpyroxime, mancozeb, chlorothalonil, fluopyram, pyraclostrobin, benzovindiflupyr, isoflurane, jiaxiangjunzhi, mandestrobin, chlorfluazuron Ipfentrifluconazole, benomyl, metyltetraprole, enoxastrobin, eugenol, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridinyl]-1-(1,2,4-triazol-1-yl)prop-2-ol, 2-[6-(4-bromophenoxy)-2- -(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)prop-2-ol, 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazol-4-carboxylon, and 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]imidazol-4-carboxylon, wherein the weight ratio of component (A) to component (B) is from 15:1 to 1:50.

[0056] In another preferred composition according to the invention, component (A) is methyl 2-(5-cyclopropyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate or a salt or tautomer thereof, and component (B) is a compound selected from the group consisting of: bifenthiophanate-methyl, chlorpyrifos, cyclophosphamide, difenoconazole, flutriafol, fenpyroxacin, hexaconazole, tebuconazole, thiophanate-methyl, propiconazole. Tebuconazole, azoxystrobin, fenpyroxime, tebuconazole, flufenoxuron, flupyraclostrobin, fenoxystrobin, fenpyroxime, fenpyroxime, fenpyroxime, azoxystrobin, fenpyroxime, mancozeb, chlorothalonil, fluopyram, pyraclostrobin, benzovindiflupyr, isoflurane, jiaxiangjunzhi, mandestrobin, chlorfluazuron Ipfentrifluconazole, benomyl, metyltetraprole, enoxastrobin, eugenol, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridinyl]-1-(1,2,4-triazol-1-yl)prop-2-ol, 2-[6-(4-bromophenoxy)-2- -(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)prop-2-ol, 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazol-4-carboxylon, and 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]imidazol-4-carboxylon, wherein the weight ratio of component (A) to component (B) is from 15:1 to 1:50.

[0057] In another preferred composition according to the invention, component (A) is methyl 2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate or a salt or tautomer thereof, and component (B) is a compound selected from the group consisting of: bifenthiophanate-methyl, chlorpyrifos, cyclophosphamide, difenoconazole, flutriafol, fenpyroxacin, hexaconazole, tebuconazole, thiophanate-methyl, propiconazole. Tebuconazole, azoxystrobin, fenpyroxime, tebuconazole, flufenoxuron, flupyraclostrobin, fenoxystrobin, fenpyroxime, fenpyroxime, fenpyroxime, azoxystrobin, fenpyroxime, mancozeb, chlorothalonil, fluopyram, pyraclostrobin, benzovindiflupyr, isoflurane, jiaxiangjunzhi, mandestrobin, chlorfluazuron Ipfentrifluconazole, benomyl, metyltetraprole, enoxastrobin, eugenol, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridinyl]-1-(1,2,4-triazol-1-yl)prop-2-ol, 2-[6-(4-bromophenoxy)-2- -(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)prop-2-ol, 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazol-4-carboxylon, and 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]imidazol-4-carboxylon, wherein the weight ratio of component (A) to component (B) is from 15:1 to 1:50.

[0058] In a more preferred composition according to the invention, component (A) is methyl 2-(5-cyclobutyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate or a salt or tautomer thereof, and component (B) is a compound selected from the group consisting of: cyclohexanil, difenoconazole, hexaconazole, prothioconazole, propiconazole, azoxystrobin, oxadiazon, pyraclostrobin, azoxystrobin, pyraclostrobin, mancozeb, chlorothalonil, fluopyram, benzovindiflupyr, isoflurane, and metronidazole, wherein the weight ratio of component (A) to component (B) is from 15:1 to 1:50.

[0059] In a more preferred composition according to the invention, component (A) is methyl 2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate or a salt or tautomer thereof, and component (B) is a compound selected from the group consisting of: cyclohexanil, difenoconazole, hexaconazole, prothioconazole, propiconazole, azoxystrobin, oxadiazon, pyraclostrobin, azoxystrobin, pyraclostrobin, mancozeb, chlorothalonil, fluopyram, benzovindiflupyr, isoflurane, and metronidazole, wherein the weight ratio of component (A) to component (B) is from 15:1 to 1:50.

[0060] In a more preferred composition according to the invention, component (A) is methyl 2-(5-cyclopropyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate or a salt or tautomer thereof, and component (B) is a compound selected from the group consisting of: cyclohexanil, difenoconazole, hexaconazole, prothioconazole, propiconazole, azoxystrobin, oxadiazon, pyraclostrobin, azoxystrobin, pyraclostrobin, mancozeb, chlorothalonil, fluopyram, benzovindiflupyr, isoflurane, and metronidazole, wherein the weight ratio of component (A) to component (B) is from 15:1 to 1:50.

[0061] In a more preferred composition according to the invention, component (A) is methyl 2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate or a salt or tautomer thereof, and component (B) is a compound selected from the group consisting of: cyclohexanil, difenoconazole, hexaconazole, prothioconazole, propiconazole, azoxystrobin, oxadiazon, pyraclostrobin, azoxystrobin, pyraclostrobin, mancozeb, chlorothalonil, fluopyram, benzovindiflupyr, isoflurane, and metronidazole, wherein the weight ratio of component (A) to component (B) is from 15:1 to 1:50.

[0062] In a preferred composition according to the invention, component (A) is methyl 2-(5-cyclobutyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate or a salt or tautomer thereof, and component (B) is a compound selected from the group consisting of: bifenthiophanate-methyl, chlorpyrifos, cyclophosphamide, difenoconazole, flutriafol, fenpyroxacin, hexaconazole, tebuconazole, thiophanate-methyl, propiconazole, tebuconazole, and azoxystrobin. Azoxystrobin, tebufenozide, fluopyram, flupyraclostrobin, fenoxystrobin, oxadiazon, oxadiazon, azoxystrobin, pyraclostrobin, pyraclostrobin, mancozeb, chlorothalonil, fluopyram, pyraclostrobin, benzovindicarb, isoflurane, jiaxiangjunzhi, mandestrobin, chlorfluazon, isofenteflufenazate (ntrifluconazole), benomyl, metyltetraprole, enoxastrobin, eugenol, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)prop-2-ol, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1- (1,2,4-triazol-1-yl)prop-2-ol, 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazol-4-carboxylon, and 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]imidazol-4-carboxylon, wherein the weight ratio of component (A) to component (B) is from 10:1 to 1:10 (or even more preferably, 7.5:1 to 1:7.5).

[0063] In another preferred composition according to the invention, component (A) is methyl 2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate or a salt or tautomer thereof, and component (B) is a compound selected from the group consisting of: bifenthiophanate-methyl, chlorpyrifos, cyclophosphamide, difenoconazole, flutriafol, fenbendazole, hexaconazole, tebuconazole, thiophanate-methyl, propiconazole, tebuconazole, pyrimethanil, etc. Azoxystrobin, fenpyroxime, oxadiazon, fluopyram, flupyraclostrobin, fenoxystrobin, oxadiazon, fenpyroxime, azoxystrobin, pyraclostrobin, mancozeb, chlorothalonil, fluopyram, pyraclostrobin, benzovindicarb, isoflurane, jiaxiangjunzhi, mandestrobin, chlorfluazon, isofenteflufenazate (ip) fentrifluconazole, benomyl, metyltetraprole, enoxastrobin, eugenol, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)prop-2-ol, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1 -(1,2,4-triazol-1-yl)prop-2-ol, 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazol-4-carboxylon, and 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]imidazol-4-carboxylon, wherein the weight ratio of component (A) to component (B) is from 10:1 to 1:10 (or even more preferably, 7.5:1 to 1:7.5).

[0064] In another preferred composition according to the invention, component (A) is methyl 2-(5-cyclopropyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate or a salt or tautomer thereof, and component (B) is a compound selected from the group consisting of: bifenthiophanate-methyl, chlorpyrifos, cyclophosphamide, difenoconazole, flutriafol, fenbendazole, hexaconazole, tebuconazole, thiophanate-methyl, propiconazole, tebuconazole, pyrimethanil, etc. Azoxystrobin, fenpyroxime, oxadiazon, fluopyram, flupyraclostrobin, fenoxystrobin, oxadiazon, fenpyroxime, azoxystrobin, pyraclostrobin, mancozeb, chlorothalonil, fluopyram, pyraclostrobin, benzovindicarb, isoflurane, jiaxiangjunzhi, mandestrobin, chlorfluazon, isofenteflufenazate (ip) fentrifluconazole, benomyl, metyltetraprole, enoxastrobin, eugenol, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)prop-2-ol, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1 -(1,2,4-triazol-1-yl)prop-2-ol, 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazol-4-carboxylon, and 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]imidazol-4-carboxylon, wherein the weight ratio of component (A) to component (B) is from 10:1 to 1:10 (or even more preferably, 7.5:1 to 1:7.5).

[0065] In another preferred composition according to the invention, component (A) is methyl 2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate or a salt or tautomer thereof, and component (B) is a compound selected from the group consisting of: bifenthiophanate-methyl, chlorpyrifos, cyclohexanil, difenoconazole, flutriafol, fenbendazole, hexaconazole, tebuconazole, thiophanate-methyl, propiconazole, tebuconazole, pyrimethanil, etc. Azoxystrobin, fenpyroxime, oxadiazon, fluopyram, flupyraclostrobin, fenoxystrobin, oxadiazon, fenpyroxime, azoxystrobin, pyraclostrobin, mancozeb, chlorothalonil, fluopyram, pyraclostrobin, benzovindicarb, isoflurane, jiaxiangjunzhi, mandestrobin, chlorfluazon, isofenteflufenazate (ip) fentrifluconazole, benomyl, metyltetraprole, enoxastrobin, eugenol, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)prop-2-ol, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1 -(1,2,4-triazol-1-yl)prop-2-ol, 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazol-4-carboxylon, and 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]imidazol-4-carboxylon, wherein the weight ratio of component (A) to component (B) is from 10:1 to 1:10 (or even more preferably, 7.5:1 to 1:7.5).

[0066] In a preferred composition according to the invention, component (A) is methyl 2-(5-cyclobutyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate or a salt or tautomer thereof, and component (B) is a compound selected from the group consisting of: cyclohexanil, difenoconazole, hexaconazole, prothioconazole, propiconazole, azoxystrobin, oxadiazon, pyraclostrobin, azoxystrobin, pyraclostrobin, mancozeb, chlorothalonil, fluopyram, benzovindiflupyr, isoflurane, and metronidazole, wherein the weight ratio of component (A) to component (B) is from 10:1 to 1:10 (or even more preferably, 7.5:1 to 1:7.5).

[0067] In another preferred composition according to the invention, component (A) is methyl 2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate or a salt or tautomer thereof, and component (B) is a compound selected from the group consisting of: cyclohexanil, difenoconazole, hexaconazole, prothioconazole, propiconazole, azoxystrobin, oxadiazon, pyraclostrobin, azoxystrobin, pyraclostrobin, mancozeb, chlorothalonil, fluopyram, benzovindiflupyr, isoflurane, and metronidazole, wherein the weight ratio of component (A) to component (B) is from 10:1 to 1:10 (or even more preferably, 7.5:1 to 1:7.5).

[0068] In another preferred composition according to the invention, component (A) is methyl 2-(5-cyclopropyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate or a salt or tautomer thereof, and component (B) is a compound selected from the group consisting of: cyclohexanil, difenoconazole, hexaconazole, prothioconazole, propiconazole, azoxystrobin, oxadiazon, azoxystrobin, pyraclostrobin, mancozeb, chlorothalonil, fluopyram, benzovindiflupyr, isoflurane, and metronidazole, wherein the weight ratio of component (A) to component (B) is from 10:1 to 1:10 (or even more preferably, 7.5:1 to 1:7.5).

[0069] In another preferred composition according to the invention, component (A) is methyl 2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate or a salt or tautomer thereof, and component (B) is a compound selected from the group consisting of: cyclohexanil, difenoconazole, hexaconazole, prothioconazole, propiconazole, azoxystrobin, oxadiazon, pyraclostrobin, azoxystrobin, mancozeb, chlorothalonil, fluopyram, benzovindiflupyr, isoflurane, and metronidazole, wherein the weight ratio of component (A) to component (B) is from 10:1 to 1:10 (or even more preferably, 7.5:1 to 1:7.5).

[0070] In a preferred composition according to the invention, component (A) is methyl 2-(5-cyclobutyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate or a salt or tautomer thereof, and component (B) is a compound selected from the group consisting of: cyclohexanil, difenoconazole, prothioconazole, azoxystrobin, oxadiazon, azoxystrobin, and metyltetraprole, wherein the weight ratio of component (A) to component (B) is from 10:1 to 1:10 (or even more preferably, 7.5:1 to 1:7.5).

[0071] In another preferred composition according to the invention, component (A) is methyl 2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate or a salt or tautomer thereof, and component (B) is a compound selected from the group consisting of: cyclohexazol, difenoconazole, prothioconazole, azoxystrobin, oxadiazon, azoxystrobin, and metyltetraprole, wherein the weight ratio of component (A) to component (B) is from 10:1 to 1:10 (or even more preferably, 7.5:1 to 1:7.5).

[0072] In another preferred composition according to the invention, component (A) is methyl 2-(5-cyclopropyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate or a salt or tautomer thereof, and component (B) is a compound selected from the group consisting of: cyclohexazol, difenoconazole, prothioconazole, azoxystrobin, oxadiazon, azoxystrobin, and metyltetraprole, wherein the weight ratio of component (A) to component (B) is from 10:1 to 1:10 (or even more preferably, 7.5:1 to 1:7.5).

[0073] In another preferred composition according to the invention, component (A) is methyl 2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate or a salt or tautomer thereof, and component (B) is a compound selected from the group consisting of: cyclohexanil, difenoconazole, prothioconazole, azoxystrobin, oxadiazon, azoxystrobin, and metyltetraprole, wherein the weight ratio of component (A) to component (B) is from 10:1 to 1:10 (or even more preferably, 7.5:1 to 1:7.5).

[0074] In one embodiment of the present invention, a synergistic antifungal composition is provided, comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is:

[0075] (Z)-2-(5-cyclobutyl-2-methylphenoxy)-3-methoxy-prop-2-enoic acid methyl ester

[0076] (Compound X.01),

[0077] (Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxy-prop-2-enoic acid methyl ester

[0078] (Compound X.02),

[0079] (Z)-2-(5-cyclopropyl-2-methylphenoxy)-3-methoxy-prop-2-enoic acid methyl ester

[0080] (Compound X.03), or

[0081] (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxy-prop-2-enoic acid methyl ester

[0082] (Compound X.04),

[0083] Or its agronomically acceptable salt;

[0084] and

[0085] Component (B) is a compound selected from the group consisting of:

[0086] Cycloconazole, difenoconazole, prothioconazole, azoxystrobin, oxadiazon, azoxystrobin, and metyltetraprole.

[0087] Preferably, in an embodiment of the present invention, a synergistic antifungal composition is provided, comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is:

[0088] (Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxy-prop-2-enoic acid methyl ester

[0089] (Compound X.02), or

[0090] (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxy-prop-2-enoic acid methyl ester

[0091] (Compound X.04);

[0092] Or its agronomically acceptable salt;

[0093] and

[0094] Component (B) is a compound selected from the group consisting of:

[0095] The mixture contains cyclophosphamide, difenoconazole, prothioconazole, azoxystrobin, oxadiazon, azoxystrobin, and metyltetraprole, wherein the weight ratio of component (A) to component (B) is from 10:1 to 1:10 (or even more preferably, 7.5:1 to 1:7.5).

[0096] More preferably, in an embodiment of the present invention, a synergistic antifungal composition is provided, comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is:

[0097] (Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxy-prop-2-enoic acid methyl ester

[0098] (Compound X.02), or

[0099] (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxy-prop-2-enoic acid methyl ester

[0100] (Compound X.04);

[0101] Or its agronomically acceptable salt;

[0102] and

[0103] Component (B) is azoxystrobin or oxadiazon, wherein the weight ratio of component (A) to component (B) is from 10:1 to 1:10 (or even more preferably, 7.5:1 to 1:7.5).

[0104] Even more preferably, in embodiments of the present invention, a synergistic antifungal composition is provided, comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is:

[0105] (Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxy-prop-2-enoic acid methyl ester

[0106] (Compound X.02), or

[0107] (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxy-prop-2-enoic acid methyl ester

[0108] (Compound X.04);

[0109] Or its agronomically acceptable salt;

[0110] and

[0111] Component (B) is azoxystrobin, wherein the weight ratio of component (A) to component (B) is from 10:1 to 1:10 (or even more preferably, 7.5:1 to 1:7.5).

[0112] In another preferred embodiment of the invention, a synergistic antifungal composition is provided, comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is:

[0113] (Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxy-prop-2-enoic acid methyl ester

[0114] (Compound X.02), or

[0115] (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxy-prop-2-enoic acid methyl ester

[0116] (Compound X.04);

[0117] Or its agronomically acceptable salt;

[0118] and

[0119] Component (B) is a compound selected from the group consisting of: cyclohexane, difenoconazole, hexaconazole, prothioconazole, propiconazole, benzyl benzoate, butyl morpholine, fludioxonil, azoxystrobin, oxadiazon, azoxystrobin, pyraclostrobin, pyraclostrobin, mancozeb, captan, chlorothalonil, fluopyram, benzalkonium chloride, isoflurane, fluopyram, chlorfluazon, pyridaben, metronidazole, N-( 2-Fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide and [(1S,2S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(4-methoxy-3-propanoyloxy-pyridine-2-carbonyl)amino]propionate (preferably, wherein the weight ratio of component (A) to component (B) is from 100:1 to 1:100).

[0120] Preferably, in this embodiment of the invention, a synergistic antifungal composition is provided, comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is:

[0121] (Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxy-prop-2-enoic acid methyl ester

[0122] (Compound X.02), or

[0123] (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxy-prop-2-enoic acid methyl ester

[0124] (Compound X.04);

[0125] Or its agronomically acceptable salt;

[0126] and

[0127] Component (B) is a compound selected from the group consisting of: cyclohexane, difenoconazole, prothioconazole, benzyl benzoate, buprofen, fludioxonil, azoxystrobin, oxadiazon, azoxystrobin, mancozeb, captan, chlorothalonil, benzo[a]fluoroquinolones, fluopyram, chlorpyrifos, pyridaben, metronidazole, N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4- [Oxadiazol-3-yl]benzamide and [(1S,2S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(4-methoxy-3-propionyloxy-pyridine-2-carbonyl)amino]propionate, wherein the weight ratio of component (A) to component (B) is from 100:1 to 1:100 (preferably from 15:1 to 1:50, more preferably from 10:1 to 1:10).

[0128] As used herein, the term "fungicide" refers to a compound that controls, alters, or prevents the growth of fungi. The term "effective fungicide amount" refers to the amount of such a compound or combination of such compounds that can affect fungal growth. Controlling or altering effects include all deviations from natural development, such as killing, inhibiting, etc., and prevention includes the formation of barriers or other defenses within or on the plant to prevent fungal infection.

[0129] The term "plant" refers to all the tangible parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, culms, leaves, and fruits.

[0130] The term "plant propagation material" refers to all reproductive parts of a plant, such as seeds or vegetative parts like cuttings and tubers. It includes seeds in the strict sense, as well as roots, fruits, tubers, bulbs, rhizomes, and other parts of the plant.

[0131] As used herein, the term "site" means the place in which or on which a plant grows, or the place where the seeds of a cultivated plant are sown, or the place where the seeds will be placed in the soil. It includes soil, seeds, and seedlings, along with the established vegetation.

[0132] Throughout this document, the term "composition" refers to different mixtures or combinations of components (A) and (B) (including the embodiments defined above), for example, in a single "ready-to-use with water" form, as a combined spray mixture (consisting of individual formulations of these single active ingredients) (e.g., a "tank mix"), and as a combination of these individual active ingredients when applied in a sequential manner (i.e., one after the other, for a suitable short period, such as hours or days). For the purposes of this invention, the order in which components (A) and (B) are applied is not critical.

[0133] The compositions according to the present invention are effective against harmful microorganisms (such as microorganisms) that cause plant pathogenic diseases, especially against plant pathogenic fungi and bacteria.

[0134] The compositions of the present invention can be used to control plant diseases caused by a broad spectrum of fungal plant pathogens belonging to the Basidiomycetes, Ascomycetes, Oomycetes and / or Deuteromycetes, Blastodactycetes, Chrytidiomycetes, Glomeromycetes and / or Mucoromycetes.

[0135] This composition effectively controls a broad spectrum of plant diseases, such as leaf pathogens in ornamental plants, turf, vegetables, fields, cereals, and fruit crops.

[0136] These pathogens may include:

[0137] Oomycetes include Phytophthora diseases, such as those caused by *Phytophthora capsici*, *Phytophthora causalina*, *Phytophthora soybeani*, *Phytophthora fragariae*, *Phytophthora nicotianae*, *Phytophthora cinnamomi*, *Phytophthora citricola*, *Phytophthora citrophthora*, and *Phytophthora erythroseptica*; Pythium diseases, such as those caused by *Pythium cucurbitae*, *Pythium arrhenomanes*, *Pythium gracilis*, *Pythium irregulare*, and *Pythium tertruncatum*; and Downycetes, such as those caused by *Peronospora destructor*, *Peronospora cabbage*, *Peronospora grapeensis*, *Peronospora sunflowerensis*, *Peronospora cucumberensis*, and *Albugo*. Diseases caused by *Candida*, rice downy mildew, and lettuce downy mildew; as well as others, such as those caused by *Sclerospora graminicola*, *Labyrinthula zosterae*, *Peronosclerospora sorghi*, and *Sclerospora graminicola*.

[0138] Ascomycetes, including diseases such as spot, blight, wilt, or downy mildew and / or rot, such as those caused by the following: *Stemphylium solani* (garlic white spot fungus), *Stagonosporatainanensis* (Tainan daffodil), *Setosphaeria turcica* (corn large leaf spot fungus), *Pyrenochaeta lycoperisici* (tomato bark fungus), *Stemphylium solani* (leaf rot fungus), *Phoma destructiva* (stem rot fungus), *Phaeosphaeria herpotrichoides* (wheat leaf dark spot fungus), *Phaeocryptocus gaeumannii* (brown cryptococcus), *Ophiosphaerella graminicola* (grass rot fungus), *Ophiobolus graminis* (wheat take-all fungus), *Leptosphaeria maculans* (cruciferous small spore fungus), *Hendersonia creberrima* (soft rot fungus), *Helminthosporium* (leaf blight fungus). Triticirepentis, Setosphaeria turcica (corn leaf spot pathogen), Drechslera glycines (soybean hymenopterus), Didymella bryoniae (watermelon vine blight pathogen), Cycloconium oleagineum (olive leaf spot pathogen), Corynespora cassiicola, Bipolaris cactivora (dragon fruit black spot pathogen), Apple black spot pathogen, Pyrenophora tritici-repentis (oat sclerotium), Alternaria brassicicola (alternaria brassicicola), Alternaria solanacea (solanum alternaria), and Alternaria tomatophila (tomatophila); Capnodiales such as Septoriaglycines (wheat spores), Septoriaglycines (soybean spores), and Cercospora (peanut causal agent). arachidicola), soybean gray spot fungus, corn gray spot fungus, capsella bursa-pastoris fungus, wheat white mold fungus (Cercosporella capsellae), wheat leaf mold fungus (Cercosporella herpotrichoides), peach scab fungus (Cladosporium carpophilum), sparse cladoceran (Cladosporium effusum), and brown mold (Passalora).* *Fructus fulva*, *Cladosporium oxysporum*, *Dothistromaseptosporum*, *Isariopsis clavispora*, *Pseudocercospora vitis*, *Mycovellosiella koepkeii*, *Phaeoisariopsis bataticola*, *Pseudocercospora vitis*, *Wheat basal rot*, *Begonia leaf spot*, *Ramularia collo-cygni*; *Metacarpaceae* such as *Tricholoma spp.*, *Magnaporthe grisea*, *Pyrrosia spp.*; *Metacarpaceae* such as *Fusarium wilt east of hazelnut*, *Apiognomonia errabunda*, *Cytospora*. platani), soybean northern stem canker fungus, *Discula destructiva*, strawberry scab (*Gnomonia fructicola*), grape bitter rot fungus, walnut black scab (*Melanconium juglandinum*), grape viticola (*Phomopsis viticola*), walnut canker fungus (*Sirococcus clavigignenti-juglandacearum*), *Tubakia dryina*, *Dicarpella* species, apple tree rot fungus (*Valsa ceratosperma*); and others, such as *Actinothyrium graminis*, pea pod spores, *Aspergillus flavus*, *Aspergillus fumigatus*, *Aspergillus nidus*, *Pachyphytum comosum*, leaf spot fungus (*Blumeriella jaapii*), *Candida* species, sooty mold fungus (*Capnodium*). ramosum), species of the genus *Cephaloascus* spp., *Cephalosporium gramineum*, *Ceratocystis paradoxa*, species of the genus *Chaetoceros*, *Hymenoscyphus pseudoalbidus*, species of the genus *Coccidioides*, *Cylindrosporium padi*, *Diplocarpon malae*, *Drepanopeziza**Campestris*, *Elsinoe ampelina*, *Coccus niger*, *Epidermophytes* species, grape top blight, *Geotrichum candida*, *Gibellina cerealis*, *Gloeocercospora sorghi*, *Gloeodes pomigena*, *Gloeosporium perennans*; endophytic fungi of dead wheat (Gloeotinia temulenta), *Griphospaeria corticola*, *Kabatiella lini*, *Leptographium microsporum*, *Leptosphaerulinia crassiasca*, *Lophodermium seditiosum*, *Marssonina graminicola*, *Microdochium nivale*, *Monilinia* (Australian type of brown rot fungus). fructicola), rice cloud-shaped disease (Monographella albescens), melon black spot root rot fungus (Monosporascus cannonballus), species of the genus *Naemacyclus* spp., new elm wilt fungus (Ophiostoma novo-ulmi), *Paracoccidioides brasiliensis*, *Penicillium expansum*, *Pestalotia rhododendri*, species of the genus *Petriellidium* spp., species of the genus *Pezicula* spp., soybean stem brown rot fungus (Phialophora gregata), pome fruit black spot fungus (Phyllachorapomigena), omnivorous hornworm (Phymatotrichum omnivora), cryptocystis (Physalospora abdita), tobacco cyst shell (Plectosporium) *Taccacidium*, *Polyscytalumpustulans*, *Pseudopeziza medicaginis*, *Pyrenopeziza brassicae*, *Ramulispora**Rhabdoclinepseudotsugaae*, *Rhynchosporium secalis*, *Sacrocladium oryzae*, *Scedosporium spp.*, *Schizothyrium pomi*, *Sclerotinia sclerotiorum*, *Sclerotinia minor*; *Sclerotium spp.*, *Typhula ishikariensis*, *Seimatosporium mariae*, *Lepteutypa cupressi*, *Septocyta ruborum*, *Sphaceloma perseae*, *Sporonemaphacidioides*, and *Stigmina*. Palmivora, Tapesiayallundae, Taphrina bullata, Thielviopsis basicola, Trichoseptoria fructigena, Zygophialajamaicensis; powdery mildew, for example, caused by Powdery Mildew fungi such as wheat powdery mildew, Polygonum powdery mildew, Grape powdery mildew, Cucumber powdery mildew (Sphaerotheca fuligena), White-forked powdery mildew, Podospaera macularis, Two-spore powdery mildew (Golovinomyces cichoracearum), Tartary powdery mildew (Leveillula taurica), Spreading powdery mildew, Oidiopsis gossypii, Phylactinia guttata, and Oidium arachifolium. Those caused by *Arachidis*; molds, such as those caused by *Botryotinia* species like *Dothiorella aromatica*, *Diplodia seriata*, *Guignardia bidwellii*, *Botrytis cinerea*, *Botryotinia allii*, and *Botryotinia spp.*Those caused by *Fabae*, *Fusicoccum amygdali*, *Lasiodiplodia theobromae*, *Macrophoma theicola*, *Coccidioidomyces chinensis*, and *Phyllosticta cucurbitacearum*; anthracnose, such as those caused by *Glommerelales* species like *Colletotrichum lagenarium*, *Colletotrichum lagenarium*, *Anthracnose spp.*, *Glommerelales*, and *Anthracnose gracilis*; and wilt or blight, such as those caused by *Hylocereus* species like *Atoporhynchus stenoptera*, *Eroxystrobinus purpureus*, *Fusarium graminearum*, *Fusarium graminearum*, *Fusarium oxysporum* f. sp. *cubense*, and *Gerlachia nigricans*. Those caused by *Gnaphalium affine*, *Gnaphalium zeylanum*, *Gnaphalium rubrum*, *Gnaphalium*, *Gnaphalium verum*, *Gnaphalium ramulariae*, *Trichoderma viride*, *Gnaphalium pinkum*, and *Verticillium theobromae*;

[0139] Basidiomycetes include diseases such as smut caused by smut fungi such as *Ustilaginoidea virens*, *Ustilago nuda*, *Ustilago tritici*, and *Ustilago zeae*, and rust diseases caused by stalk rust fungi such as *Cerotelium fici*, *Chrysomyxa arctostaphyli*, *Coleosporium ipomoeae*, *Hemileia vastatrix*, *Puccinia arachidis*, *Puccinia cacabata*, *Puccinia graminis*, *Puccinia recondita*, *Puccinia sorghi*, *Puccinia hordei*, and *Puccinia striiformis*. f.sp.Hordei), Puccinia striiformisf.sp.Those caused by *Secalis*, *Pucciniastrum coryli*; or those caused by *Ruscidea* species such as *Cronartium ribicola*, *Gymnosporangium juniperi-viginianae*, *Melampsora medusae*, *Phakopsora pachyrhizi*, *Phragmidium mucronatum*, *Physopella ampelosidis*, *Tranzschelia discolor*, and *Uromyces viciae-fabae*; and other rots and diseases, such as those caused by *Cryptococcus* species, *Exobasidium vexans*, *Marasmiellus inoderma*, *Sphagnum* species, and *Sphacelotheca*. Those caused by *Sclerotium reiliana*, *Typhula ishikariensis*, *Urocystis agropyri*, *Itersonilia perplexans*, *Corticium invisum*, *Laetisaria fuciformis*, *Waitea circinata*, *Rhizoctonia solani*, *Thanetephorus cucurmeris*, *Entyloma dahliae*, *Entylomella microspora*, *Neovossia moliniae*, and *Tilletia caries*.

[0140] Cladosporidioides, such as Physoderma maydis;

[0141] Mucormycetes, such as *Choanephora cucurbitarum*; species of the genus *Mucor*; *Rhizopus* spp.

[0142] Together with diseases caused by other species and genera closely related to those listed above.

[0143] In addition to their antifungal activity, these compositions may also have activity against bacteria such as *Pyrus pyrifolia*, *Erwinia caratovora*, *Xanthomonas laurentii*, *Pseudomonas syringae*, *Strptomyces scabies*, and other related species, along with certain protozoa.

[0144] The compositions according to the invention are particularly effective against plant pathogenic fungi belonging to the following classes: Ascomycetes (e.g., *Aureobasidium*, *Cyclocarya*, *Erythrophagus*, *Cyclocarya*, *Cyclocarya*, *Uncaria*); Basidiomycetes (e.g., *Hemileia*, *Rhizoctonia*, *Laminaria*, *Pterygophyllum*, *Ustilago*, *Ustilago*); Deuteromycetes (also known as Deuteromycetes, e.g., *Botrytis*, *Helicobacter*, *Rhizophora*, *Fusarium*, *Syndrome*, *Cercospora*, *Alternaria*, *Pyrophora*, and *Pseudocercospora*); Oomycetes (e.g., *Phytophthora*, *Peronospora*, *Pseudorhyx*, *Euphorbia*, *Plasmodium*, *Pythium*, *Pseudocercospora*, *Monocospora*).

[0145] The compositions according to the invention can be used in useful plant crops including perennial and annual crops, such as berry plants, such as blackberries, blueberries, cranberries, raspberries, and strawberries; cereals, such as barley, maize, millet, oats, rice, rye, sorghum, triticale, and wheat; fiber plants, such as cotton, flax, jute, and sisal; field crops, such as sugar beets and forage beets, coffee beans, hops, mustard, rapeseed (canola), sugarcane, sunflower, tea, and tobacco; fruit trees, such as apples, apricots, avocados, bananas, cherries, citrus fruits, nectarines, peaches, pears, and plums; and grasses, such as Bermuda grass, bluegrass, benjamin grass, centipede grass, yew grass, ryegrass, and senna grass. Cosmos and zoysia; herbs such as basil, borage, chives, coriander, lavender, angelica, mint, oregano, parsley, rosemary, sage, and thyme; legumes such as kidney beans, lentils, peas, and soybeans; nuts such as almonds, cashews, peanuts, hazelnuts, peanuts, pecans, pistachios, and walnuts; palm trees such as oil palms; ornamental plants such as flowers, shrubs, and trees; other trees such as cacao, coconut, olive, and rubber trees; vegetables such as asparagus, eggplant, broccoli, cabbage, carrots, cucumbers, garlic, lettuce, zucchini, melons, okra, onions, peppers, potatoes, squash, rhubarb, spinach, and tomatoes; and grapevines such as grapes.

[0146] Crops should be understood as those that exist naturally, are obtained through conventional breeding methods, or are obtained through genetic engineering. These include crops that possess so-called output traits (such as improved storage stability, higher nutritional value, and improved flavor).

[0147] Crops should be understood to include those that have been conferred tolerance to herbicides (like bromufenoxam) or multiple classes of herbicides (such as ALS-, EPSPS-, GS-, HPPD-, and PPO- inhibitors). Examples of crops that have been conferred tolerance to imidazolinones (e.g., methoxyfenozide) through conventional breeding methods are... Summer Canola. Examples of crops conferred herbicide tolerance through genetic engineering include, for example, glyphosate and glufosinate-resistant maize varieties, which are marketed under trademarks... Herculex and It is available for commercial purchase.

[0148] Crops should also be understood to be those that are naturally or have been conferred resistance to pests. This includes plants that, for example, are capable of synthesizing one or more selectively acting toxins through the use of recombinant DNA technology, such toxins as those known from toxin-producing bacteria. Examples of toxins that can be expressed include delta-endotoxins, vegetative insecticidal proteins (Vip), insecticidal proteins from bacterial colonizing nematodes, and toxins produced by scorpions, arachnids, wasps, and fungi.

[0149] An example of a crop that has been modified to express Bacillus thuringiensis toxin is Bt maize. (Syngenta Seeds). Examples include crops that encode insecticidal resistance and thereby express more than one gene for more than one toxin. (Syngenta Seeds). Crops or their seed material can also be resistant to multiple types of pests (so-called superimposed transgenic events when produced through genetic modification). For example, plants can express insecticidal proteins while being resistant to herbicides, such as Herculex. (Dow AgroSciences, Pioneer Hi-Bred International)

[0150] Compounds having formula (I) (including any one of compounds X.01 to X.04) or fungicidal compositions according to the invention containing compounds having formula (I) can be used to control or prevent plant pathogenic diseases on soybean plants, especially plant pathogenic fungi (such as stropharia spp.).

[0151] Specifically, transgenic soybean plants expressing toxins such as insecticidal proteins like delta-endotoxins (e.g., Cry1Ac (Cry1Ac Bt protein)). Therefore, this can include transgenic soybean plants containing event MON87701 (see U.S. Patent No. 8,049,071 and related applications and patents, and WO 2014 / 170327 A1 (see, for example, regarding Intacta RR2PRO)). TM The paragraph on soybeans

[008] ), event MON87751 (U.S. Patent Application Publication No. 2014 / 0373191) or event DAS-81419 (U.S. Patent No. 8632978 and related applications and patents).

[0152] Other transgenic soybean plants may include the following: SYHT0H2-HPPD tolerance (US Patent Application Publication No. 2014 / 0201860 and related applications and patents), MON89788-glyphosate tolerance (US Patent No. 7,632,985 and related applications and patents), MON87708-dicamba tolerance (US Patent Application Publication No. US 2011 / 0067134 and related applications and patents), DP-356043-5-glyphosate and ALS tolerance (US Patent Application Publication No. US2010 / 0184079 and related applications and patents), and A2704-12-glufosinate tolerance (US Patent Application Publication No. US 2011 / 0067134 and related applications and patents). The following events were involved: 2008 / 0320616 and related applications and patents; DP-305423-1-ALS tolerance (US Patent Application Publication No. US2008 / 0312082 and related applications and patents); A5547-127-glufosinate tolerance (US Patent Application Publication No. US 2008 / 0196127 and related applications and patents); DAS-40278-9-tolerance to 2,4-dichlorophenoxyacetic acid and aryloxyphenoxypropionate (see WO 2011 / 022469, WO 2011 / 022470, WO 2011 / 022471 and related applications and patents); 127-ALS tolerance (WO 2010 / 080829 and related applications and patents); and GTS. 40-3-2-glyphosate tolerance, event DAS-68416-4-2,4-dichlorophenoxyacetic acid and glufosinate tolerance, event FG72-glyphosate and isoxaflutole tolerance, event BPS-CV127-9-ALS tolerance and GU262-glufosinate tolerance or event SYHT04R-HPPD tolerance.

[0153] Compounds having formula (I) (including any one of compounds X.01 to X.04) or fungicidal compositions according to the invention containing compounds having formula (I) can be used to control or prevent plant pathogenic diseases on soybean plants, especially plant pathogenic fungi (such as *Solanum spp.*). In particular, certain superior soybean varieties are known in the scientific literature in which stacks of R genes conferring a certain degree of immunity or resistance to specific *Solanum spp.* have been incorporated into the plant genome, see, for example, “Fighting Asian Soybean Rust”, Langenbach C et al., Front Plant Science 7(797) 2016.

[0154] Superior plants are any plants that come from superior strains; therefore, superior plants are representative plants that come from superior varieties. Non-restricted examples of commercially available superior soybean varieties for farmers or soybean breeders include: AG00802, A0868, AG0902, A1923, AG2403, A2824, A3704, A4324, A5404, AG5903, AG6202, AG0934; AG1435; AG2031; AG2035; AG2433; AG2733; AG2933; AG3334; AG3832; AG4135; AG4632; AG4934; AG5831; AG6534; and AG7231 (Asgrow Seeds, Des Moines, Iowa, USA); BPR 0144RR, BPR 4077NRR, and BPR 4390NRR (Bio Plant Research, Camp Point, Illinois, USA); DKB17-51 and DKB37-51 (DeKalb Genetics, DeKalb, Illinois, USA); DP 4546RR and DP 7870RR (Delta & Pine Land Company, Lubbock, Texas, USA); JG03R501, JG 32R606C ADD and JG 55R503C (JGL Inc.)), Greencastle, Indiana, USA); NKS13-K2 (NK Division of Syngenta Seeds, Golden Valley, Minnesota, USA); 90M01, 91M30, 92M33, 93M11, 94M30, 95M30, 97B52, P008T22R2; P16T17R2; P22T69R; P25T51R; P34T07R2; P35T58R; P39T67R; P47T36R; P46T21R; and P56T03R2 (Pioneer Seeds International Ltd.) Hi-Bred International, Johnston, Iowa, USA; SG4771NRR and SG5161NRR / STS (Soygenetics, LLC, Lafayette, Indiana, USA); S00-K5, S11-L2, S28-Y2, S43-B1, S53-A1, S76-L9, S78-G6, S0009-M2; S00 7-Y4; S04-D3; S14-A6; S20-T6; S21-M7; S26-P3; S28-N6; S30-V6; S35-C3; S36-Y6; S39-C4; S47-K5; S48-D9; S52-Y2; S58-Z4; S67-R6; S73-S8; and S78-G6 (Syngenta Seeds, Henderson, Kentucky, USA); Richer (Northstar Seed Ltd., Alberta, Canada); 14RD62 (Stine Seed Co., Iowa, USA); or Armor 4744 (Armor Seed, LLC, Alaska, USA).

[0155] Therefore, in another preferred embodiment, the fungicidal composition according to the invention comprising a compound having formula (I) (including any of compounds X.01 to X.04) is used to control *Phyllostachys spp.* rust (including its fungicide-resistant strains, as described below) on superior soybean plant varieties, wherein the R gene stack conferring a certain degree of immunity or resistance to a particular *Phyllostachys spp.* rust has been infiltrated into the plant genome. Numerous benefits can be anticipated from this use, such as improved bioactivity, a favorable or broader spectrum of activity (including susceptible and resistant strains of *Phyllostachys spp.* rust), increased safety, improved crop tolerance, synergistic interactions or enhancing properties, improved onset or longer persistent residual activity, reduced application frequency and / or lower application rate of the compound and composition required for effective control of the plant pathogen (*Phyllostachys spp.* rust), thereby achieving beneficial resistance-management practices, reduced environmental impact, and reduced operator exposure.

[0156] In certain situations, when used to control or prevent plant pathogenic diseases, particularly plant pathogenic fungi (such as *Pseudomonas beanus*), on soybean plants (especially any genetically modified soybean plants as described above), the fungicidal compositions according to the invention containing compounds having formula (I) can exhibit synergistic interactions between the active ingredients.

[0157] The fungicidal composition according to the invention, which contains a compound having formula (I) (including any one of compounds X.01 to X.04), can be used to control or prevent plant pathogenic diseases on soybean plants, especially plant pathogenic fungi (particularly stropharia spp.).

[0158] Furthermore, to date, no cross-resistance has been observed between the fungicidal compositions according to the invention containing compounds of formula (I) (including any one of compounds X.01 to X.04) and current fungicidal solutions for controlling rust fungi in potato pods.

[0159] In fact, fungicide-resistant strains of Phakopsora pachyrhizi have been reported in the scientific literature, in which strains resistant to one or more fungicides from at least each of the following fungicidal action modes: sterol demethylation inhibitors (DMI), quinone outside inhibitors (QoI), and succinate dehydrogenase inhibitors (SDHI). See, for example: “Sensitivity of Phakopsora pachyrhizi towards quinone-outside-inhibitors and demethylation-inhibitors, and corresponding resistance mechanisms.” Schmitz HK et al., Pest Management Sci (2014) 70:378-388; “First detection of a SDH variant with reduced SDHI sensitivity in Phakopsora pachyrhizi”. K et al., J Plant Dis Prot (2018) 125:21-2; “Competitive fitness of Phakopsora pachyrhizi isolates with mutations in the CYP51 and CYTB genes.” Klosowski AC et al., Phytopathology (2016) 106:1278-1284; “Detection of the F129L mutation in the cytochrome b gene in Phakopsora pachyrhizi.” Klosowski AC et al., Pest Management Sci (2016) 72:1211-1215.

[0160] Therefore, in a preferred embodiment, the fungicidal composition according to the invention comprising a compound having formula (I) (including any one of compounds X.01 to X.04) is used to control rust fungus in the potato layer, which is resistant to one or more fungicides from any of the following fungicidal MoA classes: sterol demethylation inhibitor (DMI), quinone inhibitor (QoI), and succinate dehydrogenase inhibitor (SDHI).

[0161] The compound constituting component A of the present invention can be prepared as shown in the following scheme, wherein R 1 R 2 R 3 and R 4 As defined in equation (I).

[0162] Compounds having formula (I) (where R) 1 R 2 R 3 and R 4 As defined above, a compound of formula (II) (wherein R) can be produced via the optional presence of a metal salt (such as LiCl or ZnCl2) and a suitable metal catalyst complex (such as chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II)) in an organic solvent (such as tetrahydrofuran or 1,4-dioxane) at a temperature between 20°C and 150°C. 1 R 2 and R 3 As defined for compounds having formula (I) and R 11 It is a halide or pseudohalide such as chlorine, bromine, iodine, -OSO2CF3 or -OSO2(CF2)3CF3) and a compound having formula (III) (where R 4As defined for compounds having formula (I), and where M is a metalloid or pseudo-metalloid (e.g., M includes, but is not limited to, MgCl, ZnCl, or B(OH)2), cross-coupling transformations are obtained. For relevant examples, see: Journal of Organic Chemistry, 2010, 75, 6677-6680; Journal of the American Chemical Society, 2009, 131, 7532-7533; European Journal of Medicinal Chemistry, 2018, 147, 238-252; and “Cross-Coupling Reactions: A Practical Guide (Topics in Current Chemistry)” edited by Norio Miyaura and SLBuchwald (Springer edition), or by Armin de Meijere and... Edited by Diederich, "Metal-Catalyzed Cross-Coupling Reactions" (WILEY-VCH edition).

[0163] This is shown in Scheme 1.

[0164]

[0165] Option 1

[0166] Alternatively, compounds having formula (I) can be produced by making compounds having formula (IV) (where R...) 1 R 2 and R 3 As defined for compounds having formula (I), and R 12It is obtained by reacting partially unsaturated, optionally substituted C3-C7 cycloalkenyl groups via a reduction method (e.g., hydrogenation using a hydrogen source in the presence of a catalyst complex such as palladium on carbon, in an organic solvent such as methanol, tetrahydrofuran, or ethyl acetate, at a temperature between 0°C and 150°C). For relevant examples, see: ACS Medicinal Chemistry Letters, 2016, 7, 508-51. See also Shigeo Nishimura's 'Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis' (published by Wiley-VCH) or Johannes de Vries and Cornelis Elsevier's 'The Handbook of Homogeneous Hydrogenation' (published by Wiley-VCH). This is illustrated in Scheme 2.

[0167]

[0168] Option 2

[0169] Compounds having formula (IV) (where R) 1 R 2 and R 3 As defined for compounds having formula (I), and R 12 Partially saturated and optionally substituted C3-C7 cycloalkenyl groups can be reacted using suitable catalyst complexes such as palladium (tetra(triphenylphosphine)), in solvents such as 1,4-dioxane, dimethylformamide, or tetrahydrofuran, at temperatures between 0°C and 150°C, and optionally in the presence of a base (e.g., potassium phosphate), via a compound having formula (II) (wherein R...). 11Cross-coupling reactions are obtained by the cross-coupling of halides or pseudohalides such as chlorine, bromine, iodine, -OSO2CF3 or -OSO2(CF2)3CF3 with compounds having formula (V), where M represents a metalloid or pseudo-metalloid substance (e.g., M includes, but is not limited to, B(OH)2, BPi, SnBu3) or hydrogen. For relevant examples, see: ACS Medicinal Chemistry Letters, 2016, 7, 508-513 and “Cross-Coupling Reactions: A Practical Guide (Topics in Current Chemistry)” edited by Norio Miyaura and SLBuchwald (Springer edition), or by Armin de Meijere and... Diederich's edited work, "Metal-Catalyzed Cross-Coupling Reactions" (WILEY-VCH edition). This is shown in Scheme 3.

[0170]

[0171] Option 3

[0172] Compounds having formula (II) (where R) 1 R 2 and R 3 As defined for compounds having formula (I) and R 11 Halides or pseudohalides such as chlorine, bromine, iodine, -OSO2CF3 or -OSO2(CF2)3CF3) can be produced by compounds having formula (VI) (where R 1 R 2 and R 3 As defined for compounds having formula (I), R 11 As defined above and R 13 (Is an H or C1-C4 alkyl group) obtained by treatment with a suitable base such as sodium methoxide and a formylate such as methyl formate, optionally in a suitable solvent (e.g., tetrahydrofuran), to produce a compound having the formula (VIa) (where R is H or C1-C4 alkyl). 1 R 2 and R 3 As defined for compounds having formula (I), R 11 As defined above and R 14(It is H or methyl), and then optionally methylated with a reagent such as dimethyl sulfate in the presence of a base such as K2CO3. For relevant examples, see: Journal of Agricultural and Food Chemistry, 2007, 55, 5697-5700; Molecules, 2010, 15, 9024-9034; and Organic Process Research and Development, 2015, 19, 639-645. This is shown in Scheme 4.

[0173]

[0174] Option 4

[0175] Compounds having formula (VI) (where R) 1 R 2 and R 3 As defined for compounds having formula (I), R 11 As defined above and R 13 (is H or C1-C4 alkyl) can be produced by compounds having formula (VII) (where R is H or C1-C4 alkyl) 1 R 2 and R 3 As defined for compounds having formula (I) and R 11 As defined above, by using an organic solvent such as dimethylformamide or N-methylpyrrolidone with a base such as K2CO3 and an alkylating agent having formula (VIII) (where R...) 13 It is obtained by treatment with H or C1-C4 alkyl groups. Compounds having formula (VII) are commercially available or readily prepared from commercially available compounds by standard functional group conversion as described in March's Advanced Organic Chemistry, Smith and March, 6th ed., Wiley, 2007. This is shown in scheme 5.

[0176]

[0177] Option 5

[0178] Compounds having formula (I) (where R) 1 R 2 R 3 and R 4 As defined for compounds having formula (I), it can also be derived from compounds having formula (IX) (where R... 1 R 2 R3 and R 4 As defined for compounds having formula (I) and R 13 (Is an H or C1-C4 alkyl group) obtained by treating with a base such as sodium methoxide and a formylate such as methyl formate to produce a compound having the formula (X) (where R is an H or C1-C4 alkyl group). 1 R 2 R 3 and R 4 As defined for compounds having formula (I) and R 14 (It is H or methyl), and then methylation is carried out in the presence of a base such as K2CO3 with a reagent such as dimethyl sulfate. For relevant examples, see: Journal of Agricultural and Food Chemistry, 2007, 55, 5697-5700; Molecules, 2010, 15, 9024-9034; and Organic Process Research and Development, 2015, 19, 639-645. This is shown in Scheme 6.

[0179]

[0180] Option 6

[0181] Compounds having formula (IX) (where R) 1 R 2 and R 3 As defined for compounds having formula (I) and R 4 (Optionally substituted cyclopropyl) can be produced from compounds having formula (XI) (where R is a cyclopropyl group). 1 R 2 and R 3 As defined for compounds having formula (I) and R 15 (Indicating an optionally substituted alkenyl group) is prepared by treatment with diiodomethane, with an organozinc reagent such as diethylzinc, optionally in the presence of an acid source such as trifluoroacetic acid, and in an organic solvent such as dichloromethane. For relevant examples, see: Organic Reactions, 2001, 58, 1.

[0182] This is shown in Scheme 7.

[0183]

[0184] Option 7

[0185] Compounds having formula (XI) (where R) 1 R 2 and R3 As defined for compounds having formula (I), R 15 As defined above and R 13 (is H or C1-C4 alkyl) can be produced by compounds having the formula (XII) (where R is H or C1-C4 alkyl) 1 R 2 and R 3 As defined for compounds having formula (I) and R 15 As defined above, by using an organic solvent such as dimethylformamide or N-methylpyrrolidone with a base such as K2CO3 and an alkylating agent having formula (VIII) (where R...) 13 It is obtained by treatment with H or C1-C4 alkyl groups. This is shown in Scheme 8. For relevant examples, see: European Journal of Organic Chemistry, 2015, 2197-2204. Compounds having formula (VIII) are commercially available or readily prepared from commercially available compounds by standard functional group conversion as described in March's Advanced Organic Chemistry, Smith and March, 6th ed., Wiley, 2007.

[0186]

[0187] Option 8

[0188] Compounds having formula (XII) (where R) 1 R 2 and R 3 As defined for compounds having formula (I) and R 15 As defined above, a suitable catalyst complex such as palladium (tetra(triphenylphosphine)) can be used in a suitable solvent such as dioxane, dimethylformamide, or tetrahydrofuran at a temperature between 0°C and 150°C, and optionally with a base such as potassium phosphate or potassium carbonate, via a compound having formula (VII) (where R 1 R 2 and R 3 As defined for compounds having formula (I) and R 11 It is a halide or pseudohalide such as chlorine, bromine, iodine, -OSO2CF3 or -OSO2(CF2)3CF3) and a compound having formula (XIII) (where R 15As defined above, and where M represents the preparation of a mixture by coupling conversion between metalloids or pseudo-metalloids (e.g., M includes, but is not limited to, B(OH)₂, BPi, SnBu₃) or hydrogen). For relevant examples, see: Journal of Medicinal Chemistry, 2015, 58, 9258-9272 and Journal of Medicinal Chemistry, 2014, 57, 1252-1275. This is illustrated in Scheme 9.

[0189]

[0190] Option 9

[0191] The functional group interconversions described in the previous schemes are known to those skilled in the art. A wide list of reaction conditions can be found in: Comprehensive Organic Functional Group Transformations, edited by A.R. Katritzky, O. Meth-Cohn, and C.W. Rees, Pergamon Press (Elsevier Science Ltd.), Tarrytown, NY, 1995; or Comprehensive Organic Transformations: A Guide to Functional Group Preparations, edited by Richard C. Larock, Wiley-VCH, New York, 1999.

[0192] If the synthesis produces a mixture of isomers, separation is often not necessary because, in some cases, the individual isomers can interconvert during post-treatment for use or during application (e.g., under the influence of light, acid, or alkali). Such transformation can also occur post-use, for example, in treated plants during plant treatment or in harmful fungi to be controlled.

[0193] The compositions of the present invention, including all the embodiments and preferred examples disclosed above, can be mixed with one or more other pest control agents, including additional fungicides, insecticides, nematicides, bactericides, acaricides, growth regulators, chemical sterilizers, chemical pheromones, insect repellents, attractants, pheromones, feeding stimulants, or other bioactive compounds to form multi-component pest control agents that provide broader-spectrum agricultural protection.

[0194] Examples of such agricultural protectants and the compositions of the present invention can be formulated as follows:

[0195] Fungicides such as tebuconazole, fluazinam, benzalkonium chloride, benzalkonium chloride-M (refined benzalkonium chloride), furazolidone, metalaxyl, metalaxyl-M (refined metalaxyl), doxycycline, N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidin, N'-[4-(4,5-dichloro-thiazol-2-yloxy)-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidin, N'-[4-[[3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl]oxy]-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidin, ethamazolidine, 3'-chloro-2-methoxy-N-[(3RS)-tetrahydro-2-oxofuran-3-yl]acetyl-2',6'-di ... Methyl aniline (clozylacon), pyraclostrobin, pyraclostrobin, pyraclostrobin, dithionin, aureomycin, blast fungicide-S, biphenyl, dimethomorph, chlornitramine, benzo[a]fluoroquinolones, fluopyram, hexachlorobenzene, pentachloronitrobenzene, tetrachloronitrobenzene (TCNB), methyl thiophanate, benomyl, 2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide, fluopicolide or flupicolide, tioxymid, sulfadiazine, benomyl, carbendazim, carbendazim hydrochloride, chlorfenazole, thiabendazole, thiophanate-methyl, benomyl, thiabendazole ... Araratine benzene, bethoxazin, pyriofenone (IKF-309), araratine benzene-S-methyl, pyraclostrobin (KIF-7767), butylamine, 3-iodo-2-propynyl n-butylcarbamate (IPBC), iodocarb (isopropyl butylcarbamate), isopropyl butylcarbamate (iodocarb), tetrazolium pyrazine, polycarbamate, cymoxanil, tolprocarb, 3-(difluoromethyl)-N-(7-fluoro-1,1,3,3-tetramethyl-indan-4-yl)-1-methyl-pyrazole-4-carboxamide, dichlorocyanurate Acetaminophen, N-[(5-chloro-2-isopropyl-phenyl)methyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-pyrazole-4-carboxamide, N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-[(2-isopropylphenyl)methyl]-1-methyl-pyrazole-4-carboxamide, cyclopropionylamine, chlorothalonil, flumorph, quinoline copper (oxine-copper), cymoxanil, cyazofamid, cymoxanil, fluoxetine, thiamethoxam, ethoxysulfuron, iprodione, procymidone, fenvalerate, sulfadiazine, chlorpyrifos, oxadiazine, pyrimethanil, nitrofen, fenpyroxen, fenpyroxen, diphenylamine, chlorpyrifos, 2,6-dimethyl-[1,4]dithiazoline[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetraketone, thiram oxide, mancozeb, ferrous thiram, mancozeb zinc, mancozeb, metam, metiram or polyram, metiram-zinc, sodium mancozeb, methyl zineb, thiram, sodium thiocarbamate (vapam or metam) Sodium), Zineb, Zinc thiram, Dimethyl disulfide, Isoprothiolane, Thiazolamide, Fosetyl, Fosetyl-aluminum, Methyl bromide, Iodomethyl, Methyl isothiocyanate, Cyclomethrin, Mefenoxam, Activiacin, Streptomycin, (2RS)-2-bromo-2-(bromomethyl)glutaronitrile, Doxorubicin, Doguadine, Biguanide Octyl Salt, Biguanide Octylamine, Biguanide Octylamine Triacetate, 2,4-D, 2,4-DB, Kasugamycin, Cyclomethrin, Hymexazol, Sodium Chlorpyrifos, Imazalil, Imazalil Sulfate Sulphate), oxadiazon, isoprothiolane, imazalil, fluopyram, imazalil, Bordeaux mixture, calcium polysulfide, copper acetate, copper carbonate, copper hydroxide, copper naphthenate, copper oleate, copper oxychloride, copper hydroxyquinoline, copper silicate, copper sulfate, copper tallate, cuprous oxide, sulfur, carbaryl, tetrachlorophthalide, pyridoxine (dingjunezuo) (Jun Si) Qi), oxathiapiprolin, fluoroimide, dimethomorph, KSF-1002, benzamorf, dimethomorph, butylmorpholine, tridemorpholine, dodecylmorpholine, ethoxysulfuron, triphenyltin acetate, triphenyltin hydroxide, carbendazim, oxycarbendazim, oxadiazon, m-phenylphenol, p-phenylphenol, tribromophenol (TBP), 2-[2-[(7,8-difluoro-2-methyl-3-quinolinyl)] [2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolinyl)oxy]phenyl]propane-2-ol, cycloflufenicol, furazolidone, cymoxanil, fluopyram, cymoxanil, isofetamid, seed dressing agent, fludioxonil, pendimethalin, cyproconazole, isopyram, phosmet, phosphamidone, chlormequat chloride, captan, chlormequat chloride, phosphamidone, benzyl benzoate, benzoyl benzoate, osthol, 1-methylcyclopropene, 4-CPA, chlormequat chloride, benzoyl benzoate, 2,4-D propionic acid, thiamethoxam, cymoxanil, ethephon, flubendiamide, chlorpyrifos, gibberellic acid, gibberellin, hymexazol, maleic hydrazide, chlorothalonil, naphthylacetamide, paclobutrazol, cyclohexane, cyclohexane calcium, thiamethoxam, tributyl trithiophosphate, anti-rot acid, uniconazole, α-naphthaleneacetic acid, polyoxin D, BLAD, chitosan, cyanamide, captan, 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichlorophenyl)ethyl]pyrazole-4-carboxamide, bifenthiophanate-methyl, fluopyram, furazolidone, pyrazolenaphthylamine, pendimethalin, pyrimethanil, fluopyram, pyridaben, pyridaben, pyridaben, pyridaben Canthaxanthin, cyazofamid, fluopyram, diflubenzuron, chlorophenazine alcohol, 5-fluoro-2-(p-tolylmethoxy)pyrimidin-4-amine, pyraclostrobin, dimetachlone, dimethaclone, propoxyquin, ethoxyquin, quinoxaline, 4,4,5-trifluoro-3,3-dimethyl-1-(3-quinolinyl)isoquinoline, 4,4-difluoro-3,3-dimethyl-1-(3-quinolinyl)isoquinoline, 5-fluoro-3,3,4,4-tetramethyl-1-(3-quinolinyl)isoquinoline, 9-fluoro-2,2-dimethyl-5-(3-quinolinyl)-3H-1,4-benzoxazine, isobutylethoxyquinoline, oxolinic acid (acid), chlorpyrifos (chinomethionate or oxythioquinox, quinoxymethionate), spirocarbamide, (E)-N-methyl-2-[2-(2,5-dimethylphenoxymethyl)phenyl]-2-methoxy-iminoacetamide, (mandesbin), azoxystrobin, eugenol, fenamistrobin, enoxastrobin, fenamistrobin, fluopyram, flupyraclostrobin, fenamistrobin, mandesbin, benoxystrobin, pyraclostrobin, fenamistrobin, pyraclostrobin, chlorpyrifos, fenamistrobin, indazole sulfadiazine, bacteriostatic agent Paracetamol, methyl parathion, butyl-3-ynyl N-[6-[[(Z)-[(1-methyltetrazole-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate, dazomet, isothiazamide, thiamethoxam, thifluzamide, benzylthiocyanate (TCMTB), thiosilazamide, benzylthiocyanate, tricyclazole, (.+-.)-cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol (cyclozazole), 1-(5-bromo-2-pyridyl)-2-(2,4-difluorophenyl)-1,1-difluoro-3-(1,2,4-triazol-1-yl)propane-2-ol, 2-(1-tert-butyl)-1-(2-chlorophenyl)-3-(1,2,4-Triazol-1-yl)-propane-2-ol (TCDP), azaconazole, bifenthrin, furazolidone, clomibazole, cycloconazole, dimethoprim, dimetconazole, tebuconazole, tebuconazole-M, fluconazole, eticonazole, cyproconazole, fluquinazole, flusilazole, fenazol, hexaconazole, imidacloprid, tebuconazole, ipfentrifluconazole, tebuconazole, cyproconazole, tebuconazole, propiconazole, prothioconazole, silfluconazole, tebuconazole, tetraflufenazole, triadimefon, triadimefon, imidazolimide, cyproconazole, chlorfluazol, 2-[[(1R,5S)-5-[(4-fluorophenyl)methyl]-1-hydroxy-2,2-dimethyl [[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)ethyleneoxy-2-yl]methyl]-4H-1,2,4-triazole-3-thione, ametoctradin (or imidium), isopyram, valacyclovir, 2-benzyl-4-chlorophenol (benzylchlorophenol), allyl alcohol, pyrazosulfuron, benzalkonium chloride, chloropicrin, cresol, daracide, diclofenac (dichlorophenol), oat meal, disulfiram, N-(2-p-chlorobenzoylethyl)-hexaminium chloride, NNF-0721, octathione, pyrimisulfuron, propanemidine, and propionic acid.

[0196] Insecticides such as abamectin, chlorpyrifos, acetamiprid, sulfadiazine (S-1955), abamectin, azadirachtin, methyl glutathione, bifenthrin, bifenazate, thiamethoxam, carbofuran, batan, chlorantraniliprole (DPX-E2Y45), brofenoxam, flufenoxuron, chlorpyrifos, methyl chlorpyrifos, cyclone dichlorvos, thiamethoxam, diflubenzuron, lambda-cyhalothrin, β-cyhalothrin, and deltamethrin. λ-Cypermethrin, Cypermethrin, Cyromazine, Delmethrin, Difenoconazole, Diazinon, Dichlorvos, Diflubenzuron, Tetrafluthrin, Dimethoate, Fipronil, Benzyl ether, Emamectin, Endothiophanate-methyl, Cypermethrin, Ethylenenitrile, Benthiocarb, Fenoxycarb, Cypermethrin, Cypermethrin, Fipronil, Flupyradifurone, Flupyradifurone, T-Flumethrin, Pyrimethanil (UR-50701), Flufenoxuron, Terbufos, Chlorfenapyr Flufenoxam, flufenoxuron, imidacloprid, indoxacarb, isofenphos, lufenuron, malathion, cyfluthrin, metaldehyde, methamidophos, chlorpyrifos, methomyl, tebufenozide, methoxychloride, methoxybenzylflupyr, phosmet, methoxyfenozide, acetamiprid, nifedipine, diphenylfluorourea, polyfluorourea (XDE-007), chlorpyrifos, parathion, methyl parathion, permethrin, phorate, phosmet, phosmet, phosphamidon, pirimicarb, profenofos, propargite Pyrethroids, pymetrozine, pyrethroids, acetamiprid, flufenoxuron, pyriprole, fenproxen, rotenone, linanodin, spinosad, spinosad, spirodiclofen, spirodiclofen (BSN2060), spirotetramat, thiophanate-methyl, tebufenozide, flufenoxuron, pyrethroid, terbufos, carbendazim, thiamethoxam, thiamethoxam, thiamethoxam, chlorpyrifos, tetrabromopyr, pymetrozine, trichlorfon, and carbaryl;

[0197] Bactericides such as streptomycin;

[0198] Acaricides such as amitraz, dicofol, ethyl methacrylate, cypermethrin, tricyclic tin, trichlorfon, chlorpyrifos, etoxazole, quinclorac, fenbutatin, cypermethrin, pyridaben, thiamethoxam, dicofol, pyridaben, and pyridaben; and

[0199] Biological reagents such as Bacillus thuringiensis, Bacillus thuringiensis δ-endotoxin, baculoviruses, insect pathogens, bacteria, viruses, and fungi.

[0200] Other examples of “reference” mixture compositions are as follows (wherein the term “TX” refers to a compound selected from compound numbers X.01, X.02, X.03 or X.04 as defined in Table X above (as defined in the composition (A) according to the invention): compounds selected from the group consisting of: petroleum + TX, 1,1-bis(4-chlorophenyl)-2-ethoxyethanol + TX, 2,4-dichlorophenylbenzenesulfonate + TX, 2-fluoro-N-methyl-N-1-naphthylacetamide + TX, 4-chlorophenylphenyl sulfone + TX, acetamiprid + TX, thiamethoxam + TX, cypermethrin + TX, phosmet + TX, phosmet + TX, phosmet + TX, phosmet + TX, amitraz + TX, amitraz + TX, arsenic trioxide + TX, phosmet ... TX, Azobenzene + TX, Azophos + TX, Benomyl + TX, Benoxafos + TX, Benzyl Benzoate + TX, Bifenthrin + TX, Brofenpyraclostrobin + TX, Broflanilide + TX, Brofenoxam + TX, Brofenoxam + TX, Brofenoxam + TX, Brofenoxam + TX, Thiamethoxam + TX, Butanil + TX, Butanil Sulfonate + TX, Butylpyridinium + TX, Calcium Polysulfide + TX, Camphene + TX, Chlorpyrifos + TX, Trithion + TX, Acaricide + TX, Difenoconazole + TX, Acaricide + TX, Acaricide + TX, Acaricide + TX, Acaricide + TX, Acaricide + TX, Acaricide + TX, Acaricide + TX, Difenoconazole + TX, Ethyl Acetate + TX, Acaricide ( Chlormebuform + TX, Diflubenzuron + TX, Propyl chlorpyrifos + TX, Chlorfenapyr + TX, Ciprofloxacin I + TX, Ciprofloxacin II + TX, Ciprofloxacin + TX, Clofenac + TX, Phosphate + TX, Clomidon + TX, Phosphate + TX, Thiazol + TX, Phosphate + TX, DCPM + TX, DDT + TX, Demeton-S-methyl + TX, Demeton-O + TX, Demeton-O-methyl + TX, Demeton-S-methyl + TX, Demeton-S-methyl + TX, Demeton-S-methyl + TX, Bactericide + TX, Dichlorvos + TX, Dichlorvos (dicliphos)+TX, dicliphos+TX, fenflurphos+TX, dinex+TX, dinex-diclexine+TX, difenoconazole-4+TX, difenoconazole-6+TX, fenfenoxamyl +TX, amyl nitrate +TX, nitrocellulose +TX, butyl nitrate +TX, dichlorvos +TX, sulfadiazine +TX, disulfiram +TX, DNOC +TX, dofenapyn +TX, dofenapyn +TX, fenoxamyl +TX, fenpyrad +TX, fenpyroxim +TX, fenpyroxim +TX, fenpyroxim +TX, fenpyroxim +TXAcarbendazim + TX, fentrifanil + TX, flufenoxuron + TX, flufenoxuron + TX, fentrifanil + TX, fentrifanil + TX, fentrifanil + TX, FMC1137 + TX, fenamiphos + TX, fenamiphos hydrochloride + TX, formparanate + TX, γ-HCH + TX, fenamiphos + TX, fenamiphos + TX, fenamiphos + TX, fenamiphos + TX, cetylcyclopropane carboxylate + TX, methamidophos + TX, jasmine I + TX, jasmine II + TX, fenamiphos + TX, lindane + TX, fenamiphos + TX, fenamiphos + TX, fenamiphos + TX, dimethoate + TX, fenamiphos + TX, fenamiphos + TX, fenamiphos + TX, fenamiphos + TX, fenamiphos + TX, fenamiphos + TX, fenamiphos + TX, fenamiphos + TX, fenamiphos + TX, fenamiphos + TX Bezoar + TX, Propranolol + TX, Monocrotophos + TX, Moxifloxacin + TX, Dibromophos (naled) + TX, 4-Chloro-2-(2-chloro-2-methyl-propyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazin-3-one + TX, Flufenoxuron + TX, Nicomycin + TX, Cypermethrin + TX, Cypermethrin 1:1 Zinc Chloride Complex + TX, Omethoate + TX, Sulfonium Phosphate + TX, Sulfonium Phosphate + TX, pp'-DDT + TX, Parathion + TX, Permethrin + TX, Fenthion + TX, Phosphamidon + TX, Phosphamidon + TX, Phosphamidon + TX, Polychloroterpenes + TX, Polynactopyr + TX Ins)+TX, Prochloraz+TX, Pyrimethanil+TX, Procymidone+TX, Ethiazophos+TX, Phosphate+TX, Pyrethroid I+TX, Pyrethroid II+TX, Pyrethroid +TX, Pyridaben+TX, Pyrimethanil+TX, Quinalphos+TX, Quintiofos+TX, R-1492+TX, Glyphosate+TX, Rotenone+TX, Acephate+TX, Ketoconazole+TX, Slamethrin+TX, Thiophanate+TX, SSI-121+TX, Sufilon+TX, Fipronil+TX, Thiophanate+TX, Thiophanate+TX, Flufenoxam+TX, T-flufenoxam+TX, TEPP+TX, Terbufos+TX, Tetrachlor Acaricide sulfone + TX, Acaricide + TX, Thiafenox + TX, Insecticidal + TX, Dimethoate + TX, Methyl methamidophos + TX, Acaricide + TX, Bacillus + TX, Benomyl + TX, Triazophos + TX, Triazolon + TX, Trichloropropoxyphos + TX, Trichloropropoxyphos + TX, Amifenoxam + TX, Vaniliprole + TX, Bethoxazin + TX, Copper dioctanoate + TX, Copper sulfate + TX, 2-tert-butylamino-4-cyclopropylamino-6-methylthio-S-triazine + TX, Dichloronaphthoquinone + TX, Dichlorophenol + TX, Indomethacin + TXTriphenyltin + TX, quicklime + TX, sodium mancozeb + TX, chlorfenapyrone + TX, quinoneamine + TX, simazine + TX, triphenyltin acetate + TX, triphenyltin hydroxide + TX, phosmet + TX, piperazine + TX, thiophanate-methyl + TX, chloralose + TX, fenthion + TX, pyridine-4-amine + TX, strychnine + TX, 1-hydroxy-1H-pyridine-2-thione + TX, 4-(quinoxalo-2-ylamino)benzenesulfonamide + TX, 8-hydroxyquinoline sulfate + TX, bromonitrile + TX, copper hydroxide + TX, cresol + TX, dipyrithione +TX, Dodexin +TX, Sodium Dichlorophenate +TX, Formaldehyde +TX, Mercurochrome +TX, Kasugamycin +TX, Kasugamycin Hydrochloride Hydrate +TX, Di(Dimethyldithiocarbamate) Nickel +TX, Trichloromethylpyridine +TX, Octethione +TX, Oxytetracycline +TX, Potassium Hydroxyquinoline Sulfate +TX, Thiamethoxam +TX, Streptomycin +TX, Streptomycin Sesquisulfate +TX, Leaf Blight +TX, Thimerosal +TX, Cotton Brown Leaf Roller GV +TX, Agrobacterium Radiata +TX, Species of Amblyseius spp.)+TX, Celery Noctuid Moth NPV+TX, *Anagrus atomus*+TX, *Aphelinus abdominalis*+TX, Cotton Aphid Parasitic Wasp (*Aphidius colemani*)+TX, Aphidoletes aphidimyza*+TX, Alfalfa Silver-striped Noctuid Moth NPV+TX, *Bacillus sphaericus Neide*+TX, *Beauveria brongniartii*+TX, Common Lacewing (*Chrysoperla carnea*)+TX, *Cryptolaemus montrouzieri*+TX, Codling Moth GV+TX, Siberian Parasitic Wasp (*Dacnusa sibirica*)+TX, Pea Leafminer Fly Wasp (*Diglyphus isaea*)+TX, Encarsia aphid * *Eretmocerus eremicus* + TX, *Heterorhabditis bacteriophora* and *H. megidis* + TX, *Hippodamia convergens* + TX, *Leptomastix dactylopii* + TX, *Macrolophus caliginosus* + TX, *Nipponia cabbage noctuid moth* NPV + TX, *Metaphycus helvolus* + TXMetarhizium anisopliae var. acridum + TX, Metarhizium anisopliae var. anisopliae + TX, Neodiprion sertifer NPV and N. lecontei NPV + TX, species of the genus *Metarhizium* + TX, Paecilomyces fumosoroseus + TX, Phytoseiulus persimilis + TX, Steinernema bibionis + TX, Steinernema carpocapsae + TX, Steinernema glaseri ... riobrave)+TX, Steinernema riobravis+TX, Steinernemascapterisci+TX, Steinernema spp.+TX, Trichogramma spp.+TX, Typhlodromus occidentalis+TX, Verticillium lecanii+TX, apholate+TX, bisazir+TX, busulfan+TX, dimatif+TX, hemel+TX, hempa+TX, metepa+TX, methiotepa+TX, methyl pyrazophosphorus apholate + TX, morzid + TX, penfluron + TX, tepa + TX, thiohempa + TX, thiohempa + TX, tratamine + TX, urethaneimine + TX, (E)-dec-5-en-1-yl acetate and (E)-dec-5-en-1-ol + TX, (E)-tridec-4-en-1-yl acetate + TX, (E)-6-methylhept-2-en-4-ol + TX, (E,Z)-tetradec-4,10-dien-1-yl acetate + TX, (Z)-dodec-7-en-1-yl acetate + TX, (Z)-hexadec-11-enal + TX, (Z)-hexadec-11-en-1-yl acetate + TX, (Z)-hexadec-13-en-11-yn-1-yl acetate + TX(Z)-Eicosode-13-en-10-one + TX, (Z)-Tetradecane-7-en-1-al + TX, (Z)-Tetradecane-9-en-1-ol + TX, (Z)-Tetradecane-9-en-1-yl acetate + TX, (7E,9Z)-Dodeca-7,9-dien-1-yl acetate + TX, (9Z,11E)-Tetradecane-9,11-dien-1-yl acetate + TX, (9Z,12E)-Tetradecane-9,12-dien-1-yl Acetate + TX, 14-methyloctadec-1-ene + TX, 4-methylnon-5-ol and 4-methylnon-5-one + TX, α-polystyrin + TX, western pine bark beetle pheromone + TX, dodecadienol (codlelure) + TX, codlemone + TX, cuelure + TX, nonadecane oxide + TX, dodec-8-en-1-yl acetate + TX, dodec-9-en-1-yl acetate +TX, docosahexaenoic acid (DDO-8) +TX, 10-dien-1-yl acetate +TX, Dominicalure attractant +TX, ethyl 4-methyloctanoate +TX, Eugenol +TX, Frontalin pheromone for southern pine bark beetles +TX, Grandlure attractant +TX, Grandlure I +TX, Grandlure II +TX, Grandlure III +TX, Grandlure IV +TX, Hexalure +TX, ipsdienol +TX, ipsenol +TX, Japonilure pheromone for scarab beetles +TX, Lineatin +TX, Litlure attractant +TX, Looplure pheromone for white armyworms +TX, Medlure +TX, Megatomoic acid The following are listed as attractants: methyl eugenol + TX, muscalure + TX, octadec-2,13-dien-1-yl acetate + TX, octadec-3,13-dien-1-yl acetate + TX, orfralure + TX, oryctalure + TX, ostramone + TX, siglure + TX, sordidin + TX, sulcatol + TX, tetradec-11-en-1-yl acetate + TX, trimedlure + TX, Mediterranean fruit fly attractant A + TX, Mediterranean fruit fly attractant B1 + TX, Mediterranean fruit fly attractant B2 + TX, Mediterranean fruit fly attractant C + TX, trunc-call + TX, and 2-(octylthio)ethanol + TX.Butopyronoxyl + TX, Butoxy (polypropylene glycol) + TX, Dibutyl adipate + TX, Dibutyl phthalate + TX, Dibutyl succinate + TX, DEET + TX, Dimethyl carbate + TX, Dimethyl phthalate + TX, Ethylhexane + TX, Hexamide + TX, Methoquin-butyl + TX, Methylneodecanamide + TX, Oxamate + TX, Picaridin + TX, 1-Dichloro-1-nitrobenzene + TX, 1,1-Dichloro-2,2-bis(4-ethylphenyl)-ethane + TX, 1,2-Dichloropropane and 1,3-dichloropropene + TX, 1-Bromo-2-chloroethane + TX, 2,2,2-Trichloro-1- (3,4-Dichlorophenyl)ethyl acetate + TX, 2,2-dichlorovinyl-2-ethylsulfinyl ethyl methyl phosphate + TX, 2-(1,3-dithiopentane-2-yl)phenyl dimethyl carbamate + TX, 2-(2-butoxyethoxy)ethyl thiocyanate + TX, 2-(4,5-dimethyl-1,3-dioxolane-2-yl)phenyl methyl carbamate + TX, 2-(4-chloro-3,5-dimethylmethyloxy)ethanol + TX, 2-chlorovinyl diethyl phosphate + TX, 2-imidazolinone + TX, 2-isovaleryl indan-1,3-dione + TX, 2-methyl(prop-2-ynyl)aminophenyl methyl carbamate +TX, 2-cyanothioethyl lauryl ester +TX, 3-bromo-1-chloroprop-1-ene +TX, 3-methyl-1-phenylpyrazole-5-yldimethylcarbamate +TX, 4-methyl(prop-2-ynyl)amino-3,5-dimethylmethylcarbamate +TX, 5,5-dimethyl-3-oxocyclohex-1-enyldimethylcarbamate +TX, acethion +TX, acrylonitrile +TX, aldrin +TX, alloamycin +TX, chlorpyrifos +TX, α-decanoic acid +TX, aluminum phosphide +TX, chlorpyrifos +TX, neonicotinoid +TX, ethyl chlorpyrifos +TX, methyl pyridinium +TX, thiophanate-methyl ... Bacillus thuringiensis δ-endotoxin +TX, barium hexafluorosilicate +TX, barium polysulfide +TX, cypermethrin +TX, Bayer 22 / 190 +TX, Bayer 22408 +TX, β-cypermethrin +TX, β-cypermethrin +TX, bioethanomethrin +TX, permethrin +TX, bis(2-chloroethyl) ether +TX, borax +TX, bromophenylenephos +TX, bromo-DDT +TX, cypermethrin +TX, phosmet +TX, butathiofos +TX, butyl phosphate +TX, calcium arsenate +TX, calcium cyanide +TX, carbon disulfide +TX, carbon tetrachloride +TXBatan hydrochloride + TX, Cevadine + TX, Borneol + TX, Chlordane + TX, Decachlorophenone + TX, Chloroform + TX, Chloropicrin + TX, Chloronitrile oxime + TX, Chlorprazophos + TX, Cis-resmethrin + TX, Cismethrin + TX, Clocythrin (another name) + TX, Copper acetylacetate + TX, Copper arsenate + TX, Copper oleate + TX, Coumithoate + TX, Cryolite + TX, CS 708+TX, benzonitrile +TX, fenitrothion +TX, pyrethrum +TX, cypermethrin +TX, d-methoxyfenozide +TX, DAEP +TX, dazomet +TX, decarbofuran +TX, diamidoafos +TX, isochlorpyrifos +TX, diamidoafos +TX, dicresyl +TX, cyclophosphamide +TX, dieldrin +TX, diethyl-5-methylpyrazol-3-yl phosphate +TX, dior +TX, tetrafluoromethrin +TX, dimethoate +TX, permethrin +TX, methyl chlorpyrifos +TX, difenoconazole +TX, propanol +TX, pendimethalin +TX, diflubenzuron +TX, benzyl +TX, phosmet +TX, thiamethoxam +TX, DSP +TX, ecdysterone +TX, EI 1642+TX, EMPC+TX, EPBP+TX, etaphos+TX, ethylcarbide+TX, ethyl formate+TX, dibromoethane+TX, dichloroethane+TX, ethylene oxide+TX, EXD+TX, phosmet+TX, ethylcarbide+TX, fenitrothion+TX, fenoxacrim+TX, pyrethroids+TX, fenoxamyl+TX, ethylphosphide+TX, flucofuron+TX, phosmet+TX, phosphatidylcholine+TX, phosphatidylcholine+TX, furazolidone+TX, pyrethroids+TX, biguanide octyl salt+TX, biguanide octyl acetate+TX, sodium tetrathiocarbonate+TX, halfenp... rox)+TX, HCH+TX, HEOD+TX, heptachlor+TX, phosmet+TX, HHDN+TX, hydrogen cyanide+TX, quinoline+TX, IPSP+TX, chlorpyrifos+TX, carbamate+TX, isofenphos+TX, isofenphos+TX, transplanting agent+TX, isoprothiolane+TX, oxazinphos+TX, juvenile hormone I+TX, juvenile hormone II+TX, juvenile hormone III+TX, chlorpyrifos+TX, acetamiprid+TX, lead arsenate+TX, bromoxynil+TX, acetamiprid+TX, thiamethoxam+TX, m-isopropylphenyl methylcarbamate+TX, magnesium phosphide+TX, azoxystrobin+TX, methyl phosmet+TX, phosmet+TX, mercurous chloride+TX, methyl sulfoxide+TX.Vibrio + TX, Vibrio Potassium Salt + TX, Vibrio Sodium Salt + TX, Methylsulfonyl Fluoride + TX, Butenamphos + TX, Methoprine + TX, Permethrin + TX, Methoxydazole + TX, Methyl Isothiocyanate + TX, Methyl Chloroform + TX, Dichloromethane + TX, Imidacloprid + TX, Miperazine + TX, Naphthalide + TX, Naphthalene + TX, NC-170 + TX, Nicotine + TX, Nicotine Sulfate + TX, Nitrothiamethoxam + TX, Protonicotinic Acid + TX, O-5-di Chloro-4-iodophenyl O-ethyl ethyl thiophosphonate + TX, O,O-diethyl O-4-methyl-2-oxo-2H-benzopyran-7-yl thiophosphonate + TX, O,O-diethyl O-6-methyl-2-propylpyrimidin-4-yl thiophosphonate + TX, O,O,O',O'-tetrapropyl dithiopyrophosphate + TX, oleic acid + TX, p-dichlorobenzene + TX, methyl parathion + TX, pentachlorophenol + TX, pentachlorophenyl laurate + TX, pH 60-38+TX, Fenthion+TX, Parachlorfon+TX, Phosphine+TX, Methylphoxim+TX, Methamphetamine+TX, Polychlorinated dicyclopentadiene isomer+TX, Potassium arsenite+TX, Potassium thiocyanate+TX, Precocinone I+TX, Precocinone II+TX, Precocinone III+TX, Aminopyrimidine phosphate+TX, Procymidone+TX, Mancozeb+TX, Prothion+TX, Pyraclostrobin+TX, Pyrethrum+TX, Quassia extract+TX Quinalphos-methyl + TX, Phosphatidylcholine + TX, Isosulfanilamide + TX, Benzylfuran + TX, Rotenone + TX, Thiamethoxam + TX, Rhein + TX, Rianodin + TX, Sabadilla + TX, Octylphosphide + TX, Ketoconazole + TX, SI-0009 + TX, Thiamethoxam + TX, Sodium Arsenite + TX, Sodium Cyanide + TX, Sodium Fluoride + TX, Sodium Hexafluorosilicate + TX, Sodium Pentachlorophenolate + TX, Sodium Selenate + TX, Sodium Thiocyanate + TX Sulcofuron + TX, sulcofuron-sodium + TX, thiophanate-methyl + TX, thiophanate-methyl + TX, tar + TX, thiamethoxam + TX, TDE + TX, butylpyrimidine + TX, dithion + TX, cyclopentylpyrethrin + TX, tetrachloroethane + TX, thiamethoxam + TX, cyclophosphamide + TX, cyclophosphamide oxalate + TX, nematicide + TX, chlorpyrifos + TX, chlorpyrifos sodium + TX, tetrabromopyrethrin +TX, permethrin +TX, azoxystrobin +TX, trichlormetaphos-3 +TX, phosphamidon +TX, cypermethrin +TX, tolprocarb +TX, chlorpyrifos +TX, acetamiprid +TX, veratrine +TX, veratrine +TX, XMC +TX, zetamethrin +TX, zinc phosphide +TX, azoxystrobin +TX, and chlorpyrifos +TXTetrafluorometholone + TX, Bis(tributyltin)oxide + TX, Bromoacetamide + TX, Ferric phosphate + TX, Niclosamide-ethanolamine + TX, Tributyltin oxide + TX, Pyrmorpholine + TX, Vibrio + TX, 1,2-Dibromo-3-chloropropane + TX, 1,3-Dichloropropene + TX, 3,4-Dichlorotetrahydrothiophene 1,1-dioxide + TX, 3-(4-chlorophenyl)-5-methylrhodanine + TX, 5-Methyl-6-thio-1,3,5-thiadiazin-3-ylacetic acid + TX, 6-Isopentenylaminopurine +TX, 2-fluoro-N-(3-methoxyphenyl)-9H-purine-6-amine+TX, benclothiaz+TX, cytokinin+TX, DCIP+TX, furfural+TX, isamidophos+TX, kinetin+TX, *Lysimachia christinae* composition+TX, tetrachlorothiophene+TX, xylenol+TX, zeatin+TX, potassium ethyl xanthate+TX, aramidobenzene+TX, aramidobenzene-S-methyl+TX, *Reynoutria cuspidatum* sachalinensis extract + TX, α-chlorool + TX, antrol + TX, barium carbonate + TX, dicarboxyurene + TX, bromadiolone + TX, bromadiolone + TX, bromadiolone + TX, bromadiolone + TX, chlorpyrifos + TX, cholecalciferol + TX, chlorpyrifos + TX, cyproheptadine + TX, cyproheptadine + TX, cyproheptadine + TX, thiamethoxam + TX, cyproheptadine + TX, calciferol + TX, fluoroacetamide + TX, fluoroacetamide +TX, fluorouracil hydrochloride +TX, larvicides +TX, larvicides +TX, phosmet +TX, phosmet +TX, robin +TX, larvicides +TX, galangaloside +TX, sodium fluoroacetate +TX, thallium sulfate +TX, larvicides +TX, 2-(-2-butoxyethoxy)ethyl piperine +TX, 5-(1,3-benzodioxane-5-yl)-3-hexylcyclohex-2-enone +TX, farnesol with nerolidol +TX, synergistic acetylene ether +TX, MGK 264 +TX, synergistic ether +TX, synergistic aldehyde +TX, synergistic ester (propyl) isomer)+TX, S421+TX, Synergistic Powder+TX, Sesasmolin+TX, Sulfoxide+TX, Anthraquinone+TX, Copper Naphthenate+TX, Copper Oxide+TX, Dicyclopentadiene+TX, Ciprofloxacin+TX, Zinc Naphthenate+TX, Zinc Thiram+TX, Imanin+TX, Ribavirin+TX, Chlorindolehydrazine+TX, Mercuric Oxide+TX, Methyl Thiophanate-methyl+TX, Azaconazole+TX, Bifenthrin+TX, Fenoxacillin+TX, Cycloconazole+TX, Difenoconazole+TX, Tebuconazole+TX, Fluconazole+TX, Cyproconazole+TX, Flufenoxuron+TX, Flusilazole+TX, Tebuconazole+TX, Furazolidone+TX, Hexaconazole+TX, Imazalil+TX, Imidazole+TX, Izoxystrobin+TX, Etridiazole+TX, Izoxystrobin+TX, Cyproconazole+TXPaclobutrazol + TX, Isoprothiolane + TX, Tebuconazole + TX, Prothioconazole + TX, Pyrifenox + TX, Prochloraz + TX, Propiconazole + TX, Pyrifenox + TX, Simeconazole + TX, Tebuconazole + TX, Flufenoxuron + TX, Triadimefon + TX, Triadimefon + TX, Fluconazole + TX, Mefenoxuron + TX, Pyrimidine + TX, Chlorpheniramine + TX, Flupheniramine + TX, Bupirimate + TX, Dimethirimol + TX, Ethirimol + TX, Dodecyl Morpholine + TX, Fenpropidin + TX, Butyl... Benzomorpholine + TX, Spirocyclophosphamide + TX, Tridemorpholine + TX, Azoxystrobin + TX, Azoxystrobin + TX, Pyrimethanil + TX; Seed dressing agent + TX, Fludioxonil + TX, Benalaxyl + TX, Furalaxyl + TX, Metalaxyl + TX, R-Methoxystrobin + TX; Furazolidone + TX; Oxadixyl + TX, Carbendazim + TX, Debacarb + TX, Wheat bran + TX, Thiabendazole + TX, Chlozolinate + TX, Dichlozoline + TX, Myclozoline + TX The following are listed: procymidone + TX, vinclozoline + TX, boscalid + TX, carbendazim + TX, methomyl + TX, flutolanil + TX, oxadiazon + TX, penthiopyrad + TX, thifluzamide + TX, doxycycline + TX, biguanidine + octylamine + TX, azoxystrobin + TX, ethoxystrobin + TX, enestroburin + TX, enestroburin + TX, fluopyram + TX, fluopyram + TX, ethoxystrobin + TX, fenoxystrobin + TX, azoxystrobin + TX, azoxystrobin + TX, pyraclostrobin + TX, difenoconazole ... Azoxystrobin + TX, azoxystrobin + TX, azoxystrobin + TX, azoxystrobin + TX, ferram + TX, mancozeb + TX, mancozeb + TX, mancozeb + TX, methyl mancozeb + TX, mancozeb + TX, captan + TX, captan + TX, flufenoxuron + TX, captan + TX, paraben + TX, Bordeaux mixture + TX, copper oxide + TX, mancozeb + TX, quinoline copper + TX, phthalimide + TX, chlorpyrifos + TX, isoprothiolane + TX, chlorpyrifos + TX, methyl thiophanate + TX, difenoconazole + TX, blasticidin + TX, chloroneb + ​​TX, chlorothalonil + TX, cycloflufenoconazole + TXCymoxanil + TX, Cyclobutrifluram + TX, Diclocymet + TX, Diclomezine + TX, Dicloran + TX, Diethofencarb + TX, Dimethomorph + TX, Flumorph + TX, Dithianon + TX, Ethaboxam + TX, Etridiazole + TX, Oxadiazon + TX, Fenamidone + TX, Fenoxanil + TX, Ferimzon e) + TX, fluazinam + TX, fluopicolide + TX, flusulfamide + TX, fluoxazin + TX, cyclophosphamide + TX, fosetyl-aluminium + TX, hymexazol + TX, propineb + ​​TX, cyazofamid + TX, methasulfocarb + TX, benomyl + TX, pencycuron + TX, phthalyl + TX, polyoxins + TX, propamocarb b) +TX, pyraclostrobin +TX, proquinazid +TX, pyroquilon +TX, pyriofenone +TX, quinoxalic acid +TX, pentachloronitrobenzen +TX, thiamethoxam +TX, triazine +TX, tricyclazole +TX, pyrazosulfuron +TX, valvaline +TX, zoxamide +TX, mandipropamid +TX, flufenoxuron +TX, isopyrazam +TX, sedaxane +TX, benzovindiflubenzuron +TX, fluopyram +TX, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3',4',5'-trifluoro-biphenyl-2-yl)-amide +TX, isofluram +TX, isothiazamine +TX, dipymetitrone +TX, 6-ethyl-5,7-dioxo-pyrrolo[4,5][1,4]dithiainro[1,2-c]isothiazol-3-carboxynitrile +TX, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide +TX, 4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine-3-carboxynitrile +TX,(R)-3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide + TX, 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazole-3-amine + TX, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine + TX, fluindapyr + TX, jiaxiangjunzhi + TX, lvbenmixianan + TX, dichlobentiazox + TX, Man Mandestrobin + TX, 3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinoline-1-yl)quinolone + TX, 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinoline)oxy]phenyl]prop-2-ol + TX, oxathiapiprolin + TX, N-[6-[[[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]tert-butyl carbamate + TX, piraziflumid + TX, inpyrfluxam + TX, tripka (trolproca) rb)+TX, chlorfluazuron+TX, isofentefluconazole+TX, 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide+TX, N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidin+TX, N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidin+TX, [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 +TX, N-[6-[[(Z)-[(1-methyltetrazole-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate butyl-3-yne ester +TX, N-[[5-[4-(2,4-dimethylphenyl)triazol-2-yl]-2-methyl-phenyl]methyl]carbamate methyl ester +TX, 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine +TX, pyridachlometyl +TX, 3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide +TX,1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one + TX, 1-methyl-4-[3-methyl-2-[[2-methyl-4-(3,4,5-trimethylpyrazol-1-yl)phenoxy]methyl]phenyl]tetrazol-5-one + TX, aminopyrifen + TX, azoxystrobin + TX, indazolesulfonamide + TX, fluopyram + TX, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide + TX, pyridabenamide + TX, fenpyroximate Fenpicoxamid + TX, Isobutylethoxyquin + TX, Ipflufenoquin + TX, Quinofumelin + TX, Iprothiamethoxam + TX, N-[2-[2,4-dichloro-phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide + TX, N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide + TX, Benzyl ester + TX, Cyanobacterium ester + TX, 5-amino-1,3,4-thiadiazole-2-thiol zinc salt (2:1) + TX, Fluopyram Amide + TX, Fluoxetine + TX, Fluoxetine + TX, Pyrapropoyne + TX, Piperazine + TX, 2-(Difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indane-4-yl)pyridine-3-carboxamide + TX, 2-(Difluoromethyl)-N-((3R)-1,1,3-trimethylindane-4-yl)pyridine-3-carboxamide + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, Meteltetrapro (metyltetraprole)+TX, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide+TX, α-(1,1-dimethylethyl)-α-[4'-(trifluoromethoxy)[1,1'-diphenyl]-4-yl]-5-pyrimidinemethanol+TX, fluoxapiprolin+TX, enoxastrobin+TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile+TX,4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioalkyl-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thio-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, anti-acid + TX, eugenol + TX, kasugamycin + TX, thiamethoxam + TX, thiamethoxam + TX, amectotractin + TX, iprodione + TX, N-oct-N'-[2-(octamino)ethyl]ethane-1,2-diamine + TX; N'-[5-bromo-2-methyl-6-[(1S)-1- [Methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidin + TX, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidin + TX, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidin + TX, N'-[5-chloro-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidin + TX, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidin + TX (these compounds can be derived from WO Prepared by the method described in 2015 / 155075); N'-[5-bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidin + TX (this compound can be prepared by the method described in IPCOM000249876D); N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenyl-ethyl)phenyl]-N-methyl-formamidin + TX, N'-[4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-methoxy-2-methyl-phenyl]-N-isopropyl-N-methyl-formamidin + TX (these compounds can be prepared by WO Prepared by the method described in WO 2018 / 228896); N-ethyl-N'-[5-methoxy-2-methyl-4-[2-trifluoromethyl)oxetane-2-yl]phenyl]-N-methyl-formamidin + TX, N-ethyl-N'-[5-methoxy-2-methyl-4-[2-trifluoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methyl-formamidin + TX (these compounds can be prepared by the method described in WO 2019 / 110427); N-[(1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide + TX,N-[(1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1R)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide + TX, 8-fluoro-N-[(1R)-1-[(3-fluorophenyl)methyl]-1 [3-Dimethyl-Butyl]quinoline-3-carboxamide + TX, 8-fluoro-N-[(1S)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide + TX, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide + TX, N-((1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide + TX, N-((1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide + TX (these compounds can be derived from WO4) (Prepared by the method described in 2017 / 153380);

[0201] 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline + TX, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,6-trifluoro-3,3-dimethyl-isoquinoline + TX, 4,4-difluoro-3,3-dimethyl-1-(6-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline + TX, 4,4-difluoro-3,3-dimethyl-1-(7-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline + TX, 1-(6-chloro-7-methylpyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline + TX (these compounds can be derived from WO4) Prepared by the method described in 2017 / 025510); 1-(4,5-dimethylbenzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline + TX, 1-(4,5-dimethylbenzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline + TX, 6-chloro-4,4-difluoro-3,3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline + TX, 4,4-difluoro-1-(5-fluoro-4-methyl-benzimidazol-1-yl)-3,3-dimethyl-isoquinoline + TX, 3-(4,4-difluoro-3,3-dimethyl-1-isoquinoline)-7,8-dihydro-6H-cyclopentadien[e]benzimidazol + TX (these compounds can be prepared by WO Prepared by the method described in 2016 / 156085); [(1S,2S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propionate + TX, [(1S,2S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propionate + TX, [(1S,2S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(4-methoxy-3-propanoyloxy-pyridine-2-carbonyl)amino]propionate + TX, [(1S,2S)-2-(4-fluoro-2-methyl ... [(1S,2S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl](2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propionate + TX, [(1S,2S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl](2S)-2-[(4-methoxy-3-propionyloxy-pyridine-2-carbonyl)amino]propionate + TX, [(1S,2S)-2-(4-fluoro-2-methyl-phenyl)-1,3-dimethyl-butyl](2S)-2-[(4-methoxy-3-propionyloxy-pyridine-2-carbonyl)amino]propionate + TX, N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-Oxadiazol-3-yl]phenyl]methyl]cyclopropaneformamide + TX, N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide + TX, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide + TX, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea + TX, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea + TX, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]phenyl [4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide + TX, 4,4-dimethyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidine-3-one + TX, 5,5-dimethyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidine-3-one + TX, 4-Oxadiazol-3-yl]phenyl]methyl]isoxazolidine-3-one + TX, 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylic acid ethyl ester + TX, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-1,2,4-triazol-3-amine + TX. The compounds in this paragraph can be prepared by the methods described in WO 2017 / 055473, WO 2017 / 055469, WO 2017 / 093348 and WO 2017 / 118689; 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)prop-2-ol + TX (this compound can be prepared by the method described in WO 2017 / 029179); 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-Triazol-1-yl)prop-2-ol + TX (this compound can be prepared by the method described in WO 2017 / 029179); 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazol-4-carboxynitrile + TX (this compound can be prepared by the method described in WO 2016 / 156290); 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]imidazol-4-carboxynitrile + TX (this compound can be prepared by the method described in WO 2016 / 156290); 2-amino-6-methyl-pyridine-3-carboxylic acid (4-phenoxyphenyl) methyl ester + TX (this compound can be prepared by WO 2017 / 029179); Prepared by the method described in WO 2014 / 006945); 2,6-dimethyl-1H,5H-[1,4]dithiobenzo[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetraone + TX (this compound can be prepared by the method described in WO 2011 / 138281); N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiobenzamide + TX; N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX; (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide + TX (this compound can be prepared by the method described in WO 2014 / 006945); Prepared by the method described in WO 2018 / 153707); N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidin + TX; N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidin + TX (this compound can be prepared by the method described in WO 2016 / 202742); 2-(difluoromethyl)-N-[(3S)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide + TX (this compound can be prepared by the method described in WO 2018 / 153707); Prepared by the method described in WO 2014 / 095675); (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl] ketone + TX, (3-methylisoxazol-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl] ketone + TX (these compounds can be prepared by the method described in WO 2017 / 220485); 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide + TX (this compound can be prepared by the method described in WO 2018 / 065414); 1-[[5-[5-(trifluoromethyl)-1,2,[4-Oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylic acid ethyl ester + TX (this compound can be prepared by the method described in WO 2018 / 158365); 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide + TX, N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX, N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX, N-[N-methoxy-C-methyl-carboimino]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX (these compounds can be prepared by the method described in WO 2018 / 158365); 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX (these compounds can be prepared by the method described in WO 2018 / 158365) The method described in 2018 / 202428 is used to prepare biostimulants (Quantis). TM (It contains organic carbon, nutrients and amino acids) +TX.

[0202] References in parentheses following the active ingredient, such as [3878-19-1], refer to Chemical Abstracts Registry Numbers. The mixtures described above are known. In cases where the active ingredient is included in "The Pesticide Manual" [The Pesticide Manual - A World Compendium; 13th Edition; edited by CDSTomLin; The British Crop Protection Coimcil], they are described therein by the entry number given in parentheses above for the specific compound; for example, the compound "avermectin" is described by entry number (1). In cases where "[CCN]" is added above for a specific compound, the compound is included in "Compendium of Pesticide Common Names," which is available on the Internet [A.Wood; Compendium of PesticideCommonNames , [1995-2004] obtained; for example, the compound "acetaminophen" is described at an Internet address http: / / www.alanwood.net / pesticides / acetoprole.html

[0203] Most of the aforementioned active ingredients are referred to above by their so-called “generic names,” with the corresponding “ISO generic name” or another “generic name” used in individual cases. If the name is not a “generic name,” the type of name used is replaced by the name given in parentheses for the specific compound; in this case, the IUPAC name, IUPAC / Chemical Abstracts name, “chemical name,” “common name,” “compound name,” or “development code” is used, or if neither of those names nor a “generic name” is used, an “alias” is used. “CAS Registry Number” refers to the Chemical Abstracts Registry Number.

[0204] In the “Reference” mixture composition, the mixture of compounds having formula (I) (selected from Table X (above)) and the active ingredients described above comprises compounds selected from Table X (above) and the active ingredients as described above, preferably in a mixing ratio from 100:1 to 1:100, especially from 50:1 to 1:50, more especially from 20:1 to 1:20, even more especially from 10:1 to 1:10, even more especially from 7.5:1 to 1:7.5, very especially from 5:1 and 1:5, particularly preferably from 2:1 to 1:2, and ratios from 4:1 to 2:1 are also preferred, especially from 1: 1. Ratios of 5:1, 5:2, 5:3, 5:4, 4:1, 4:2, 4:3, 3:1, 3:2, 2:1, 1:5, 2:5, 3:5, 4:5, 1:4, 2:4, 3:4, 1:3, 2:3, 1:2, 1:600, 1:300, 1:150, 1:35, 2:35, 4:35, 1:75, 2:75, 4:75, 1:6000, 1:3000, 1:1500, 1:350, 2:350, 4:350, 1:750, 2:750, or 4:750. These mixing ratios are by weight.

[0205] The above-described mixtures (all according to the present invention and “reference” mixtures) can be used in methods for controlling pests, the method comprising applying a composition containing the mixtures described above to the pest or its environment.

[0206] A mixture comprising compounds of formula (I) selected from Table X (above) and one or more active ingredients as described above may be applied, for example, as a single "ready-to-use" preparation, as a combined spray mixture (consisting of individual formulations of these single active ingredients) (such as a "bucket mix"), and in combination when applied in a sequential manner (i.e., one after another after a moderately short period, such as hours or days). The order in which these compounds of formula (I) selected from Table X (above) and these active ingredients as described above are applied is not critical to the implementation of this invention.

[0207] These compositions of the present invention can also be used for crop enhancement. According to the present invention, 'crop enhancement' means improved plant vigor, improved plant quality, improved tolerance to stress factors, and / or improved input utilization efficiency.

[0208] According to the present invention, 'improvement of plant vigor' means that certain traits are improved in quality or quantity when compared with the same traits of control plants that have been grown under the same conditions but without using the method of the present invention. Such traits include, but are not limited to, earlier and / or improved germination, improved emergence, ability to use fewer seeds, increased root growth, more developed root system, increased root nodulation, increased bud growth, increased tillering, stronger tillering, more efficient tillering, increased or improved plant uprightness, less plant verse (lodging), increased and / or improved plant height, increased plant weight (fresh or dry weight), larger leaves, greener leaf color, increased pigment content, increased photosynthetic activity, earlier flowering, longer panicles, earlier grain maturity, increased seed, fruit, or pod size, increased number of pods or ears, increased number of seeds per pod or ear, increased seed quality, enhanced seed filling, fewer dead basal leaves, delayed wilting, improved plant vigor, increased levels of amino acid compounds in storage tissues, and / or the need for less input (e.g., less fertilizer, water, and / or labor required). Plants with improved vitality may have an increase in any of the above traits or any combination thereof, or in two or more of the above traits.

[0209] According to the present invention, 'improvement of plant quality' means that certain traits are improved in quality or quantity when compared with the same traits of control plants that have been grown under the same conditions but without using the method of the present invention. Such traits include, but are not limited to, improved visual appearance of plants, reduced ethylene (reduced production and / or inhibited reception), improved quality of harvested materials (e.g., seeds, fruits, leaves, vegetables), (such improved quality can manifest as improved visual appearance of harvested materials, improved carbohydrate content (e.g., increased sugar and / or starch content, improved sugar-acid ratio, reduced reducing sugars, increased rate of sugar formation), improved protein content, improved oil content and composition, improved nutritional value, reduced anti-nutritional compounds, improved sensory properties (e.g., improved taste) and / or improved consumer health benefits (e.g., increased vitamin and antioxidant levels)), improved post-harvest characteristics (e.g., enhanced shelf life and / or storage stability, easier processability, easier compound extraction), more homogeneous crop development (e.g., simultaneous germination, flowering, and / or fruiting of plants) and / or improved seed quality (e.g., for use in subsequent seasons). Plants with improved quality may have increases in any of these traits or any combination thereof, or in two or more of the aforementioned traits.

[0210] According to the present invention, improved tolerance to stress factors means that certain traits are qualitatively or quantitatively improved compared to the same traits in control plants under the same conditions lacking the method of the present invention. Such traits include, but are not limited to, increased tolerance and / or resistance to a variety of abiotic stress factors that induce suboptimal growth conditions, such as drought (e.g., any stress leading to a lack of plant water content, a lack of water absorption potential, or reduced water supply to the plant), cold, heat, osmotic stress, UV stress, flooding, increased salinity (e.g., salinity in the soil), increased mineral exposure, ozone exposure, high light exposure, and / or limited nutrient (e.g., nitrogen and / or phosphorus) utilization. Plants with improved tolerance to stress factors may have increased tolerance to any of the above-described traits or any combination thereof, or to two or more of the above-described traits. In the case of drought and nutrient stress, these improvements in tolerance may be attributed to, for example, more efficient absorption, utilization, or retention of water and nutrients.

[0211] According to the present invention, 'improved input utilization efficiency' means that a plant is able to use a given input level more efficiently than a control plant grown under the same conditions but without using the method of the present invention. Specifically, these inputs include, but are not limited to, fertilizers (such as nitrogen, phosphorus, potassium, and micronutrients), light, and water. Plants with improved input utilization efficiency may have improved use of any of the above-described inputs, or any combination of two or more of the above-described inputs.

[0212] Other crop enhancements of the present invention include reducing plant height or reducing tillering, which are beneficial features in crops or under conditions where less biomass and fewer tillers are desired.

[0213] Any or all of the above crop enhancements can result in improved yields by improving, for example, plant physiology, plant growth and development, and / or plant architecture. In the context of this invention, 'yield' includes, but is not limited to: (i) increases in biomass production, cereal yield, starch content, oil content, and / or protein content, which may result from: (a) an increase in the amount produced by the plant itself or (b) an improved ability to harvest plant material, (ii) improvements in the composition of the harvested material (e.g., improved sugar-acid ratio, improved oil composition, increased nutritional value, reduction of anti-nutritional compounds, increased consumer health benefits) and / or (iii) an increased / facilitated ability to harvest crops, improved crop processability, and / or better storage stability / shelf life. An increase in the yield of agricultural plants means, where quantitative measurement is possible, a measurably greater yield of a particular product of a particular plant than the yield of the same product produced by that plant under the same conditions (but without the application of this invention). According to the invention, preferably, this yield increase is at least 0.5%, more preferably at least 1%, even more preferably at least 2%, still more preferably at least 4%, preferably 5%, or even higher.

[0214] Any or more crop enhancements can also lead to land use improvements, meaning that land previously unusable or suboptimal for planting can become usable. For example, plants that show enhanced survival under drought conditions can be grown in areas with suboptimal rainfall (e.g., perhaps on the edge of a desert or even in the desert itself).

[0215] In one aspect of the invention, crop enhancement is achieved under conditions where stress from pests and / or diseases and / or abiotic stresses is substantially absent. In another aspect of the invention, improvements in plant vigor, stress tolerance, quality, and / or yield are achieved under conditions where stress from pests and / or diseases is substantially absent. For example, pests and / or diseases can be controlled by applying pest-killing treatments before or simultaneously with the method of the invention. In yet another aspect of the invention, improvements in plant vigor, stress tolerance, quality, and / or yield are achieved under conditions where pest and / or disease stress is absent. In further embodiments, improvements in plant vigor, quality, and / or yield are achieved under conditions where abiotic stresses are absent or substantially absent.

[0216] These compositions of the present invention can also be used in the field of protecting stored goods from fungal attack. According to the invention, the term "stored goods" should be understood to refer to natural substances of plant and / or animal origin and their processed forms, derived from their natural life cycle and intended for long-term protection. Plant-derived stored goods (such as plants or parts thereof (e.g., stems, leaves, tubers, seeds, fruits, or grains)) can be protected in a freshly harvested state or in a processed form (e.g., pre-dried, moistened, crushed, ground, or baked). Also falling under the definition of stored goods is timber, whether in log form, such as building timber, transmission towers, and fences, or in the form of finished products, such as furniture or objects made from timber. Animal-derived stored goods are hides, leather, fur, hair, etc. The compositions according to the invention can prevent adverse effects such as decay, fading, or mold. Preferably, "stored goods" should be understood to refer to natural substances of plant origin and / or their processed forms, more preferably fruits and their processed forms (e.g., pome, stone fruit, berries, and citrus fruits and their processed forms). In another preferred embodiment of the invention, "stored goods" should be understood to mean timber.

[0217] Therefore, another aspect of the present invention is a method for protecting stored goods, the method comprising applying a composition according to the present invention to the stored goods.

[0218] The compositions of the present invention can also be used in the field of protecting technical materials from fungal attack. According to the present invention, the term "technical material" includes paper; blankets; buildings; cooling and heating systems; wall panels; ventilation and air conditioning systems, etc.; preferably, "technical material" should be understood to refer to wall panels. The compositions according to the present invention can prevent adverse effects such as decay, fading, or mold growth.

[0219] The compositions according to the invention are typically formulated in a variety of ways using formulation aids (such as carriers, solvents, and surfactants). These formulations can be in various physical forms, for example, as powders, gels, wettable powders, water-dispersible granules, water-dispersible tablets, effervescent compressed tablets, emulsifiable concentrates, microemulsifiable concentrates, oil-in-water emulsions, flowable oils, aqueous dispersions, oily dispersions, suspensions, capsule suspensions, emulsifiable granules, soluble liquids, water-soluble concentrates (with water or a water-miscible organic solvent as a carrier), impregnated polymer films, or in other known forms, such as those described in the Manual on Development and Use of FAO and WHO Specifications for Pesticides, United Nations, 1st Edition, Second Revision (2010). Such formulations can be used directly or diluted before use. It can be diluted with, for example, water, liquid fertilizer, micronutrients, biological organisms, oil or solvents.

[0220] These formulations can be prepared, for example, by mixing the active ingredients with formulation aids to obtain compositions in the form of finely dispersed solids, particles, solutions, dispersions, or emulsions. These active ingredients can also be formulated with other aids, such as finely dispersed solids, mineral oils, oils of plant or animal origin, modified oils of plant or animal origin, organic solvents, water, surfactants, or combinations thereof.

[0221] These active ingredients can also be encapsulated in microcapsules. Microcapsules contain the active ingredient within a porous carrier. This allows the active ingredient to be released into the environment in a controlled amount (e.g., slow release). Microcapsules typically have a diameter from 0.1 to 500 micrometers. The amount of active ingredient they contain is approximately 25% to 95% by weight of the capsule. These active ingredients can be in the form of a monolithic solid, fine particles in a solid or liquid dispersion, or in a form suitable for solution. The encapsulating membrane can contain, for example, natural or synthetic rubber, cellulose, styrene / butadiene copolymers, polyacrylonitrile, polyacrylates, polyesters, polyamides, polyureas, polyurethanes, or chemically modified polymers, as well as starch xanthates, or other polymers known to those skilled in the art. Alternatively, very fine microcapsules can be formed in which the active ingredient is contained in the form of finely dispersed particles within a solid matrix of the base material, but these microcapsules themselves are not encapsulated.

[0222] Formulation aids suitable for preparing formulations according to the present invention are known in themselves. As liquid carriers, the following can be used: water, toluene, xylene, petroleum ether, vegetable oil, acetone, methyl ethyl ketone, cyclohexanone, acid anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone, butenyl carbonate, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetate, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethyl... Formamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, dipropylene glycol, alkylpyrrolidone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1,1,1-trichloroethane, 2-heptanone, α-pinene, d-limonene, ethyl lactate, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, γ-butyrolactone, glycerol, glyceryl acetate, glyceryl diacetate, glyceryl triacetate, deca-acetate, etc. Hexadecane, hexanediol, isopentyl acetate, isobornyl acetate, isooctane, isophorone, cumene, isopropyl myristate, lactic acid, laurylamine, isopropyl acetone, methoxypropanol, methyl isopentyl ketone, methyl isobutyl ketone, methyl lauryl ketone, methyl octanoate, methyl oleate, dichloromethane, m-xylene, n-hexane, n-octylamine, octadecanoic acid, octylamine acetate, oleic acid, oleyleneamine, o-xylene, phenol, polyethylene glycol, propionic acid, propyl lactate Propylene carbonate, propylene glycol, propylene glycol methyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylenesulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol methyl ether, diethylene glycol methyl ether, methanol, ethanol, isopropanol, and alcohols with higher molecular weights, such as pentanol, tetrahydrofuranol, hexanol, octanol, ethylene glycol, propylene glycol, glycerol, N-methyl-2-pyrrolidone, etc.

[0223] Suitable solid carriers include, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, diatomaceous earth, limestone, calcium carbonate, bentonite, calcium montmorillonite, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, ground walnut shells, lignin, and similar substances.

[0224] Many surfactants can be advantageously used in both solid and liquid formulations, especially those that can be diluted with a carrier before use. Surfactants can be anionic, cationic, nonionic, or polymeric, and they can be used as emulsifiers, wetting agents, suspending agents, or for other purposes. Typical surfactants include, for example, salts of alkyl sulfates, such as diethanolammonium dodecyl sulfate; salts of alkyl aryl sulfonates, such as calcium dodecylbenzenesulfonate; alkylphenol / olefin oxide addition products, such as ethoxylated nonylphenol; alcohol / olefin oxide addition products, such as ethoxylated tridecyl alcohol; soaps, such as sodium stearate; salts of alkyl naphthalene sulfonates, such as sodium dibutylnaphthalene sulfonate; salts of dialkyl sulfosuccinates, such as sodium di(2-ethylhexyl)sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary ammonium compounds, such as dodecyltrimethylammonium chloride; polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of monoalkyl and dialkyl phosphate esters; and other substances, such as those described in McCutcheon's Detergents and Emulsifiers Annual, MC Publishing. Corp.), Ridgewood, New Jersey (1981).

[0225] Other adjuvants that can be used in formulations for killing pests include crystallization inhibitors, viscosity modifiers, suspending agents, dyes, antioxidants, foaming agents, light absorbers, mixing aids, defoamers, complexing agents, substances that neutralize or change pH and buffer solutions, corrosion inhibitors, fragrances, wetting agents, absorption enhancers, micronutrients, plasticizers, flow aids, lubricants, dispersants, thickeners, antifreeze agents, microbial agents, and liquid and solid fertilizers.

[0226] Formulations according to the invention may include additives comprising oils of vegetable or animal origin, mineral oils, alkyl esters of such oils, or mixtures of such oils with oil derivatives. The amount of oil additive in the formulations according to the invention is typically from 0.01% to 10% of the mixture to be applied. For example, the oil additive may be added to the spray can at the desired concentration after the spray mixture has been prepared. Preferred oil additives include mineral oils or vegetable oils, such as rapeseed oil, olive oil, or sunflower oil; emulsified vegetable oils; alkyl esters of vegetable oils, such as methyl derivatives; or animal oils, such as fish oil or tallow. Preferred oil additives include C8-C... 22 Alkyl esters of fatty acids, especially C 12 -C 18Methyl derivatives of fatty acids, such as lauric acid, palmitic acid, and methyl esters of oleic acid (methyl laurate, methyl palmitate, and methyl oleate, respectively). Many oil derivatives are known in the Compendium of Herbicide Adjuvants, 10th edition, Southern Illinois University, 2010.

[0227] These formulations typically contain, by weight, from 0.1% to 99%, particularly from 0.1% to 95% of the compounds of components (A) and (B), and by weight, from 1% to 99.9% of formulation aids, which preferably include, by weight, from 0% to 25% of surfactants. Commercial products may preferably be formulated as concentrates, while end users will typically use diluted formulations.

[0228] Application rates vary over a wide range and depend on soil properties, application method, crop species, pests to be controlled, primary climatic conditions, and other factors governed by application method, application time, and target crop. Generally, compounds can be applied at rates ranging from 1 l / ha to 2000 l / ha, particularly from 10 l / ha to 1000 l / ha.

[0229] Certain mixtures of compounds having formula (I) described above can exhibit synergistic effects. This synergistic effect occurs whenever the combined effect of the active ingredients is greater than the sum of the effects of the individual components. For a given combination of active ingredients, the expected effect E follows the so-called Colby formula and can be calculated as follows (COLBY, SR, "Calculating synergistic and antagonistic responses of herbicide combination," Weeds, Vol. 15, pp. 20-22; 1967):

[0230] ppm = number of milligrams of active ingredient (=ai) per liter of spray mixture

[0231] X = % effect of active ingredient (based on active ingredient A) using p ppm.

[0232] Y = % effect of active ingredient (based on active ingredient B) using q ppm of active ingredient.

[0233] According to Colby, using active ingredients at p+q ppm, the expected effect of (additive) active ingredients A)+B) is:

[0234]

[0235] If the observed effect (O) is greater than the expected effect (E), then the combined effect is superadditive, i.e., a synergistic effect exists. Mathematically, a synergistic effect corresponds to a positive value of the difference (OE). In the case of purely complementary addition of the active ingredient (expected activity), the difference (OE) is zero. A negative value of the difference (OE) indicates a loss of activity compared to the expected activity.

[0236] However, in addition to the actual synergistic effect relative to the fungicidal activity, the compositions according to the invention may also have other unexpectedly advantageous properties. Examples of such advantageous properties that may be mentioned are: more favorable degradability; improved toxicological and / or ecotoxicological behavior; or improved characteristics of useful plants, including: emergence, crop yield, more developed root system, increased tillering, increased plant height, larger leaves, less basal leaf mortality, stronger tillering, greener leaf color, less fertilizer required, less seed required, more tillering, earlier flowering, earlier grain maturity, less lodging, enhanced bud growth, improved plant vigor, and earlier germination.

[0237] The compositions according to the invention can be applied to plant pathogenic microorganisms, useful plants, their sites, their propagation materials, stored goods, or technical materials threatened by microbial attack.

[0238] The composition according to the invention can be applied before or after useful plants, their propagation materials, stored goods or technical materials are infected by microorganisms.

[0239] The amount of the composition according to the invention to be applied will depend on various factors, such as the compound used; the object to be treated, such as plants, soil or seeds; the type of treatment, such as spraying, dusting or seed dressing; the purpose of the treatment, such as prevention or treatment; the type of fungus to be controlled or the timing of application.

[0240] Typically, when component (A) is applied to a useful plant in combination with component (B), which is typically applied at a ratio of 5 to 2000 g ai / ha, particularly 10 to 1000 g ai / ha, such as 100 g ai / ha, 250 g ai / ha, 500 g ai / ha, 800 g ai / ha, 1000 g ai / ha, or 1500 g ai / ha, component (A) is typically applied at a ratio of 5 to 2000 g ai / ha, particularly 10 to 1000 g ai / ha, such as 50 g ai / ha, 75 g ai / ha, 100 g ai / ha, or 200 g ai / ha.

[0241] In agricultural practice, the application rate of the composition according to the invention depends on the type of desired effect and is typically in the range of 20 to 4000 g of total composition per hectare.

[0242] When the composition according to the invention is used to treat seeds, a ratio of 0.001 to 50 g of component (A) compound per kg of seeds, preferably 0.01 to 10 g per kg of seeds, and 0.001 to 50 g of component (B) compound per kg of seeds, preferably 0.01 to 10 g per kg of seeds, is generally sufficient.

[0243] To avoid any doubt, when citing references, patent applications, or patents in the text of this application, the full text of the cited references is incorporated herein by reference.

[0244] Example

[0245] The following examples illustrate the invention.

[0246] The compounds (and compositions) of the present invention may differ from known compounds (and compositions) in that they have greater potency at lower application rates, which can be demonstrated by those skilled in the art using the experimental procedures outlined in the examples, with one or more active ingredients at lower application rates (if necessary), for example, 50 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1.5 ppm or 0.2 ppm.

[0247] Throughout this specification, temperatures are given in degrees Celsius, and "mp" indicates melting point. LC / MS stands for Liquid Chromatography-Mass Spectrometry, and the apparatus and methods are described below:

[0248] Method G:

[0249] Spectra were recorded on a mass spectrometer (SQD, SQDII single quadrupole mass spectrometer) from Waters Corporation, equipped with an electro-jet source (polarity: positive and negative ions), capillary voltage: 3.00 kV, cone range: 30 V, extractor: 2.00 V, source temperature: 150 °C, desolvation temperature: 350 °C, cone gas flow rate: 50 L / h, desolvation gas flow rate: 650 L / h, mass range: 100 Da to 900 Da) and an Acquity UPLC from Waters Corporation: binary pump, heated column chamber, diode array detector, and ELSD detector. Column: Waters UPLC HSS T3, 1.8 μm, 30 × 2.1 mm, temperature: 60 °C, DAD wavelength range (nm): 210 to 500, solvent gradient: A = water + 5% MeOH + 0.05% HCOOH, B = acetonitrile + 0.05% HCOOH; gradient: 10%-100% B, over 1.2 min; flow rate (mL / min): 0.85.

[0250] Method H:

[0251] Spectra were recorded on a mass spectrometer (SQD, SQDII single quadrupole mass spectrometer) from Waters Corporation, equipped with an electro-jet source (polarity: positive and negative ions), capillary voltage: 3.00 kV, cone range: 30 V, extractor: 2.00 V, source temperature: 150 °C, desolvation temperature: 350 °C, cone gas flow rate: 50 L / h, desolvation gas flow rate: 650 L / h, mass range: 100 Da to 900 Da) and an Acquity UPLC from Waters Corporation: binary pump, heated column chamber, diode array detector, and ELSD detector. Column: Waters UPLC HSS T3, 1.8 μm, 30 × 2.1 mm, temperature: 60 °C, DAD wavelength range (nm): 210 to 500, solvent gradient: A = water + 5% MeOH + 0.05% HCOOH, B = acetonitrile + 0.05% HCOOH; gradient: 10%-100% B, over 2.7 min; flow rate (mL / min): 0.85.

[0252] If necessary, the final compound, which is pure in the enantiomeric sense, can be obtained from racemic material via standard physical separation techniques (e.g., reversed-phase chiral chromatography) or via stereoselective synthesis techniques (e.g., by using chiral starting materials).

[0253] Examples of preparations

[0254]

[0255] The active ingredient and excipients are thoroughly mixed and the mixture is thoroughly ground in a suitable grinder to provide a wettable powder that can be diluted with water to give a suspension of the desired concentration.

[0256]

[0257] The active ingredient is thoroughly mixed with the adjuvant and the mixture is thoroughly ground in a suitable grinder to provide a powder that can be used directly for seed treatment.

[0258] Emulsifiable concentrate

[0259]

[0260] Emulsions with any required dilution that can be used in plant protection can be obtained by diluting such concentrates with water.

[0261]

[0262] Ready-to-use powders are obtained by mixing the active ingredient with a carrier and grinding the mixture in a suitable grinder. These powders can also be used for dry seed dressing.

[0263] Extruder Particles

[0264]

[0265]

[0266] The active ingredient and excipients are mixed and ground, and the mixture is moistened with water. The mixture is then extruded and dried in an air stream.

[0267] Coated particles

[0268] Active ingredients [components (A) and (B)] 8%

[0269] Polyethylene glycol (molecular weight 200) 3%

[0270] 89% Kaolin

[0271] The finely ground active ingredient is evenly applied to kaolin clay moistened with polyethylene glycol in a mixer. This process yields dust-free coated particles.

[0272] suspension concentrate

[0273]

[0274] Finely ground active ingredients are closely mixed with excipients to obtain a suspension concentrate, from which a suspension concentrate can be diluted with water to obtain a suspension of any desired dilution. Using such dilutions, living plants along with their propagation material can be treated and protected against microbial infections by spraying, watering, or immersion.

[0275] Flowable concentrate for seed treatment

[0276]

[0277]

[0278] Finely ground active ingredients are closely mixed with excipients to obtain a suspension concentrate, from which a suspension concentrate can be diluted with water to obtain a suspension of any desired dilution. Using such dilutions, living plants along with their propagation material can be treated and protected against microbial infections by spraying, watering, or immersion.

[0279] Sustained-release capsule suspension

[0280] A mixture of 28 parts of the active ingredients [components (A) and (B)] was mixed with 2 parts of an aromatic solvent and 7 parts of a toluene diisocyanate / polymethylene-polyphenyl isocyanate mixture (8:1). This mixture was emulsified in a mixture of 1.2 parts of polyvinyl alcohol, 0.05 parts of an antifoaming agent, and 51.6 parts of water until the desired particle size was achieved. 2.8 parts of a 1,6-hexanediamine mixture in 5.3 parts of water was added to this emulsion. The mixture was stirred until polymerization was complete. The resulting capsule suspension was stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersant. This capsule suspension formulation contained 28% of the active ingredient. The diameter of the medium capsules was 8-15 micrometers. The resulting formulation was applied to seeds as an aqueous suspension suitable for this purpose.

[0281] List of abbreviations:

[0282] Aq.=Water-based

[0283] br s = broad single peak

[0284] ℃ = Celsius

[0285] DCM = dichloromethane

[0286] dd = double peak

[0287] DMF = dimethylformamide

[0288] DMSO = dimethyl sulfoxide

[0289] DMSO-d6 = deuterated dimethyl sulfoxide

[0290] d = double peak

[0291] EtOAc = Ethyl acetate

[0292] equiv. = equivalent

[0293] h = hours

[0294] M = mole

[0295] m = multiplet

[0296] min = minutes

[0297] MHz = Megahertz

[0298] mp = melting point

[0299] Pd2(dba)3=tris(dibenzylacetone)dipalladium(0)

[0300] Pd(dppf)Cl2·DCM=[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloroDCM complex

[0301] Pd(PPh3)2Cl2=bis(triphenylphosphine)palladium(II) dichloride

[0302] ppm = parts per million

[0303] RT = room temperature

[0304] R t =Retention time

[0305] s = single peak

[0306] t = triple peak

[0307] THF = Tetrahydrofuran

[0308] LC / MS = Liquid Chromatography-Mass Spectrometry (The above provides a description of the apparatus and methods used for LC / MS analysis).

[0309] X-Phos Pd G2=chloro(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II)

[0310] Preparation example:

[0311] Example 1: This example illustrates the preparation of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate (compound X.04).

[0312] Step 1: Preparation of methyl 2-(5-bromo-2-methylphenoxy)acetate

[0313]

[0314] Potassium carbonate (2 equivalents, 106.9 mmol, 14.78 g) was added to a solution of 5-bromo-2-methylphenol (53.47 mmol, 10.00 g) and methyl 2-bromoacetate (1.5 equivalents, 80.20 mmol, 12.27 g, 7.44 mL) in tetrahydrofuran (0.5 mol / L, 106.9 mL). The light brown suspension was heated to 65 °C for 2 h, then cooled to room temperature overnight. The reaction mixture was diluted with EtOAc and washed with water. The aqueous phase was extracted with EtOAc, and the combined organic phase was washed with water and brine, dried over Na₂SO₄, filtered, and concentrated under vacuum to give methyl 2-(5-bromo-2-methylphenoxy)acetate (47.22 mmol, 15.89 g, 88% yield) as a brown liquid. The crude oil was slightly contaminated with residual methyl 2-bromoacetate but was used directly for the next step without further purification.

[0315] LCMS (Method H), Rt = 1.59 min, MS: (M+1) = 259, 261; 1 H NMR

[0316] (400MHz, CDCl3) δppm 2.25 (s, 3H) 3.84 (s, 3H) 4.66 (s, 2H) 6.84 (d, 1H) 7.05 (m, 2H)

[0317] Step 2: Preparation of (Z)-2-(5-bromo-2-methylphenoxy)-3-methoxy-prop-2-enoic acid methyl ester

[0318]

[0319] Part 1: Sodium methoxide (20 equivalents, 161 mmol, 9.13 g) was added fractionally to a solution of 2-(5-bromo-2-methylphenoxy)acetate (20.8 g, 80.3 mmol) and methyl formate (6.0 equivalents, 482 mmol, 29.5 g, 30.5 mL) in tetrahydrofuran (0.5 mol / L, 161 mL). The reaction was slightly exothermic and maintained below 30 °C with the aid of a room temperature water bath. The reaction mixture was stirred at room temperature for 1 h and quenched by slow addition of a saturated aqueous solution of NaHCO3. The two phases were separated and the aqueous phase was extracted with EtOAc. The total combined organic layers were washed with a saturated aqueous solution of NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated under vacuum to give methyl 2-(5-bromo-2-methylphenoxy)-3-hydroxy-prop-2-enoate, which could be used directly for the next step without further purification.

[0320] LCMS (method G), Rt = 0.80 and 0.90 min, MS: (M+1) = 287, 289

[0321] Part 2: Potassium carbonate (1.5 equivalents, 117 mmol, 16.3 g) was added to a solution of crude methyl 2-(5-bromo-2-methyl-phenoxy)-3-hydroxy-prop-2-enoate and dimethyl sulfate (1.2 equivalents, 93.2 mmol, 11.8 g, 8.8 mL) in DMF (0.5 mol / L, 155 mL) at room temperature, and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was quenched by slow addition of water, and the mixture was extracted with EtOAc. The total combined organic layers were washed with a saturated aqueous solution of NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated under vacuum. The residue was purified by rapid chromatography (cyclohexane: EtOAc) to give methyl (Z)-2-(5-bromo-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as a grayish-white solid (59.6 mmol, 18.0 g, 75% yield).

[0322] LCMS (method G), Rt = 1.02 min, MS: (M+1) = 301, 303; 1 H NMR

[0323] (400MHz, CDCl) 3 )δppm 2.31(s,3H)3.74(s,3H)3.91(s,3H)6.86(d,1H)7.05(m,2H)7.35(s,1H)

[0324] Step 3: Methyl (Z)-2-[5-(cyclohexen-1-yl)-2-methylphenoxy]-3-methoxy-prop-2-enoate preparation

[0325]

[0326] To a solution of (Z)-2-(5-bromo-2-methylphenoxy)-3-methoxy-prop-2-enoate (203 mg, 0.67 mmol, 1.00 equivalent) in 1,4-dioxane (6 mL) and water (1 mL), cyclohexen-1-ylboronic acid (93.4 mg, 0.74 mmol, 1.10 equivalent), potassium phosphate (295 mg, 1.35 mmol, 2.00 equivalent), and X Phos Pd G2 (53.0 mg, 0.07 mmol, 0.10 equivalent) were added. The reaction mixture was stirred at 100 °C for 15 min and the heat source was removed. After the contents reached room temperature, they were diluted with EtOAc and saturated NaHCO3 aqueous solution, and then extracted with EtOAc. All combined organic fractions were washed with saturated NaHCO3 aqueous solution and brine, dried over Na2SO4, filtered, and concentrated under vacuum. The residue was purified by rapid chromatography (cyclohexane: EtOAc) to obtain methyl (Z)-2-[5-(cyclohexen-1-yl)-2-methylphenoxy]-3-methoxy-prop-2-enoate as an amorphous solid.

[0327] LC-MS (Method G), R t =1.17min, MS:(M+H)=303; 1 H NMR (400)

[0328] MHz, CDCl3)δppm 7.36(s,1H),7.11(d,1H),6.96(dd,1H),6.77(d,1H),6.04(m,1H),3.90(s,3H),3 .74(s,3H),2.36(m,5H),2.17-2.25(m,2H),1.74-1.83(m,2H),1.63-1.71(m,2H).

[0329] Step 4: Preparation of (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester (compound X.04)

[0330]

[0331] Palladium / carbon (23.2 mg, 0.01 mmol, 0.02 equivalents) was added to a solution of (Z)-2-[5-(cyclohexen-1-yl)-2-methylphenoxy]-3-methoxy-prop-2-enoate (132 mg, 0.44 mmol, 1.00 equivalents) in hexane (0.87 mL) and EtOAc (2.18 mL). The reaction mixture was stirred for 2 days under a hydrogen atmosphere. The reaction mixture was filtered through diatomaceous earth and concentrated under vacuum. The resulting crude residue was purified by rapid chromatography (cyclohexane: EtOAc) to give (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxy-prop-2-enoate as a white solid (mp: 131 °C–132 °C).

[0332] LC-MS (Method G), R t =1.21min, MS:(M+H)=305; 1 H NMR (400)

[0333] MHz, CDCl3)δppm ppm 7.35(s,1H),7.10(d,1H),6.79(dd,1H),6.58(d,1H),3.90(s,3H),3.74(s,3H),2.38-2.47( m,1H),2.34(s,3H),1.80-1.89(m,4H),1.75(br,1H),1.33-1.42(m,4H),1.22-1.32(m,1H).

[0334] Example 2: This example illustrates the preparation of methyl (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate (compound X.02).

[0335]

[0336] Under an argon atmosphere, a 1M THF solution (2.54 mmol) of zinc chloride was added to a 2M THF solution (2.54 mmol) of cyclopentylmagnesium bromide, and the pale yellow suspension was stirred at room temperature for 10 min, during which a small exothermic reaction was observed. Subsequently, a solution of (Z)-2-(5-bromo-2-methyl-phenoxy)-3-methoxy-prop-2-enoate (0.153 g, 0.51 mmol) in tetrahydrofuran (2.5 mL) and PdCl2 (dppf) (0.19 g, 0.025 mmol) were added, and the pale yellow suspension was heated at 50 °C for 3 h. The reaction mixture was then allowed to reach room temperature, quenched with a saturated aqueous NH4Cl solution, and extracted with methyl tert-butyl ether. The total combined organic fraction was then washed with water and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by rapid chromatography (cyclohexane:EtOAc gradient) to give 0.106 mg of the title compound as a white solid (mp 80℃-83℃).

[0337] LC-MS (Method G), R t =1.16min, MS:(M+H)=291; 1 H NMR (400)

[0338] MHz, CDCl3)δppm:7.35(s,1H),7.09(d,1H),6.82(d,1H),6.60(s,1H),3.90(s,3H),3.72(s,3H),2. 91(m,1H),2.32(s,3H),2.10-1.97(m,2H),1.85-1.75(m,2H),1.74-1.65(m,2H),1.60-1.45(m,2H).

[0339] Accordingly, compounds having formula (I) can be prepared using the above and the following synthetic techniques.

[0340] If necessary, the final compound, which is pure in the enantiomeric sense, can be obtained from racemic material via standard physical separation techniques (e.g., reversed-phase chiral chromatography) or via stereoselective synthesis techniques (e.g., using chiral starting materials), when appropriate.

[0341] Table T1: Melting point (mp) data of compounds X.01 to X.04 according to formula (I) and / or Retention time (Rt):

[0342]

[0343]

[0344] Biological examples:

[0345] A typical example of leaf disc testing in an orifice plate:

[0346] Leaf discs or segments of different plant species were cut from plants grown in a greenhouse. The cut leaf discs or segments were placed on water agar in a multi-well plate (24-well). The leaf discs were sprayed with a test solution before (preventative) or after (cure) inoculation. The compound to be tested was prepared as a DMSO solution (maximum 10 mg / mL) and diluted to the appropriate concentration with 0.025% Tween 20 just before spraying. The inoculated leaf discs or segments were incubated under defined conditions (temperature, relative humidity, light, etc.) according to the corresponding test system. Depending on the disease system, a single assessment of disease level was performed 3 to 14 days post-inoculation. The percentage of disease control relative to untreated test leaf discs or segments was then calculated.

[0347] A typical example of liquid culture testing in well plates:

[0348] Fungal mycelial fragments or conidial suspensions (prepared fresh from liquid culture of the fungus or from cryopreservation) were directly mixed into nutrient broth. A DMSO solution of the test compound (maximum 10 mg / mL) was diluted 50-fold with 0.025% Tween 20, and 10 μl of this solution was pipetted into a microtiter plate (96-well). Nutrient broth containing fungal spores / mycelial fragments was then added to obtain the final concentration of the test compound. The test plate was incubated in the dark at 24°C and 96% relative humidity. Depending on the disease system, inhibition of fungal growth was determined photometrically after 2 to 7 days, and the percentage of antifungal activity relative to the untreated test sample was calculated.

[0349] Example A1: Fungicidal agents against Puccinia recondita f. sp. tritici, a type of wheat rust fungus. Active / Wheat / Leaf Disc Prevention Method (Brown Rust)

[0350] Wheat leaf segments were placed on agar in a multi-well plate (24-well size) and sprayed with the test solution. After drying, the leaf segments were inoculated with a suspension of fungal spores. After appropriate incubation, the activity of the compound was assessed at 8 dpi (days after incubation) as prophylactic fungicidal activity.

[0351] When compared with an untreated control exhibiting extensive disease development under the same conditions, the following compounds provided at least 80% control of wheat rust at 200 ppm:

[0352] Compounds (from Table T1): X.01, X.02, X.03, X.04

[0353] Example A2: Fungicidal activity against wheat cryptic rust fungus / wheat / leaf disc treatment (brown rust)

[0354] Wheat leaf segments were placed on agar in a multi-well plate (24-well size). The leaf segments were inoculated with a suspension of fungal spores and sprayed with a test solution one day after inoculation. After appropriate incubation, the activity of the compound was evaluated at 8 dpi (days after incubation) as therapeutic fungicidal activity.

[0355] When compared with an untreated control exhibiting extensive disease development under the same conditions, the following compounds provided at least 80% control of wheat rust at 200 ppm:

[0356] Compounds (from Table T1): X.01, X.02, X.04

[0357] Example A3: Fungicidal activity against soybean rust fungus / Soybean / Leaf disc prevention method (Asian soybean rust)

[0358] Soybean leaf discs were placed on agar in a 24-well plate and sprayed with the test solution. After drying, the leaf discs were inoculated with a suspension of fungal spores. After appropriate incubation, the activity of the compound was assessed as preventative fungicidal activity at approximately 12 dpi (days after incubation).

[0359] When compared with an untreated control exhibiting extensive disease development under the same conditions, the following compounds provided at least 70% control of *Potato Bean* rust fungus at 60 ppm:

[0360] Compounds (from Table T1): X.01, X.02, X.03, X.04

[0361] Example A4: Targeting *Glomerella lagenarium* (a fungus causing cucurbit anthracnose) (Colletotrichum lagenarium) liquid culture antifungal activity / cucumber / prevention method (anthrax)

[0362] Frozen-stored fungal conidia were directly mixed into nutrient broth (PDB potato dextrose broth). A DMSO solution of the test compound was placed in a microtiter plate (96-well size), and nutrient broth containing the fungal conidia was added. These test plates were incubated at 24°C, and the inhibition of growth was determined spectrophotometrically at 620 nm after 72 hours.

[0363] When compared with an untreated control showing extensive disease development under the same conditions, the following compounds provided at least 80% control of *Trichophyton mentagrophytes* at 20 ppm:

[0364] Compounds (from Table T1): X.01, X.02, X.03, X.04

[0365] Comparison data:

[0366] The bioactivity of compounds X.02 and X.04 of the present invention was compared with that of reference compounds Z-1 and Z-2. Reference compounds Z-1 and Z-2 are specifically disclosed on page 16 of WO 98 / 03464 and page 6 of EP 0 212 859, respectively.

[0367] Example B: Comparative bioactivity against wheat rust (brown rust), therapeutic:

[0368] Methods: Wheat leaf segments were placed on agar in a multi-well plate (24-well). The leaf segments were inoculated with a fungal spore suspension and sprayed with a test solution one day after inoculation. After appropriate incubation, the activity of the compound was assessed at 8 dpi (days after incubation) as therapeutic fungicidal activity.

[0369] The data are presented as the percentage of disease control and testing rate for each compound in the biological tests described in Table B1 below.

[0370] Table B1 - Bioactivity against wheat rust (brown rust), therapeutic:

[0371]

[0372] Further examples of biological testing involving antifungal compositions containing a mixture of components (A) and (B) as active ingredients:

[0373] Example C1 targets *Mycosphaerella arachidis*, also known as the peanut brown spot pathogen. Fungicidal activity against (Cercospora arachidicola) (brown leaf spot disease).

[0374] Frozen fungal conidia were directly mixed into nutrient broth (PDB potato dextrose broth). A DMSO solution of the test compound was placed in a microtiter plate (96-well size), and nutrient broth containing the fungal conidia was added. These test plates were incubated at 24°C, and the inhibition of growth was determined spectrophotometrically at 620 nm after approximately 5–6 days.

[0375] When compared with an untreated control exhibiting extensive disease development under the same conditions, the following compound mixtures provided at least 80% control of *Mycosphaerella arachidis* at the ratios listed in the table:

[0376] Table C1-1 - For Mycosphaerella arachidis Antifungal Activity >80% (untreated %)

[0377]

[0378]

[0379]

[0380]

[0381]

[0382]

[0383]

[0384]

[0385]

[0386] Table C1-2 - For Mycosphaerella arachidis Its antifungal activity is >80%. (Unprocessed %)

[0387]

[0388]

[0389]

[0390]

[0391]

[0392]

[0393]

[0394]

[0395]

[0396]

[0397] In this test (Mycosphaerella arachidis, also known as Cercospora arachidicola (peanut brown leaf spot)), the following mixtures were used to provide disease control at the concentrations (in ppm) reported in Tables C1-3 and C1-4. Fungicidal activity was evaluated on a 100-0 scale (100 = no disease growth; 0 = complete mycelial coverage).

[0398] Table C1-3

[0399]

[0400]

[0401] Table C1-4

[0402]

[0403]

[0404] Example C2 - Antifungal activity against wheat scab (blister spot disease)

[0405] Frozen-stored fungal conidia were directly mixed into nutrient broth (PDB potato dextrose broth). A DMSO solution of the test compound was placed in a microtiter plate (96-well size), and nutrient broth containing the fungal conidia was added. These test plates were incubated at 24°C, and the inhibition of growth was determined photometrically after 72 hours.

[0406] When compared with an untreated control that showed extensive disease development under the same conditions, the following compound mixtures provided at least 80% control of wheat scab at the ratios listed in the table.

[0407] Table C2-1 - For wheat shell needle spore Its fungicidal activity is >80% (untreated %).

[0408]

[0409]

[0410]

[0411]

[0412]

[0413]

[0414]

[0415] Table C2-2 - Fungicidal activity against wheat styrax >80% (untreated %)

[0416]

[0417]

[0418]

[0419]

[0420]

[0421]

[0422]

[0423]

[0424] In this test (Wheat spore (blister spot)), the following mixtures provided the following disease control at the concentrations (in ppm) reported in Tables C2-3 to C2-5. Fungicidal activity was evaluated on a 100-0 scale (100 = no disease growth; 0 = complete mycelial coverage).

[0425] Table C2-3

[0426]

[0427]

[0428]

[0429] Table C2-4

[0430]

[0431]

[0432] Table C2-5

[0433]

[0434]

[0435]

[0436]

[0437]

[0438] Example C3 - Fungicidal activity against *Septoria glycines* (brown spot disease):

[0439] Fungal conidia harvested from fresh cultures grown on artificial media were directly mixed into nutrient broth (PDB potato dextrose broth). A DMSO solution of the test compound was placed in a microtiter plate (96-well size), and nutrient broth containing fungal spores was added. These test plates were incubated at 24°C, and the inhibition of growth was determined photometrically after 72 hours.

[0440] When compared with an untreated control exhibiting extensive disease development under the same conditions, the following compound mixtures provided at least 80% control of *Septoria glycines* at the ratios listed in the table:

[0441] Table C3-1 - For Septoria glycines (soybean septoria) Its antifungal activity is >80%. (Unprocessed %)

[0442]

[0443]

[0444]

[0445]

[0446]

[0447]

[0448]

[0449]

[0450]

[0451] Table C3-2 - For Septoria glycines (soybean septoria) Its antifungal activity is >80%. (Unprocessed %)

[0452]

[0453]

[0454]

[0455]

[0456]

[0457]

[0458]

[0459]

[0460]

[0461]

[0462]

[0463] In this test (Septoria glycines (brown spot)), the following mixtures provided the following disease control at the concentrations (in ppm) reported in Tables C3-3 to C3-5. Fungicidal activity was evaluated on a 100-0 scale (100 = no disease growth; 0 = complete mycelial coverage).

[0464] Table C3-3

[0465]

[0466]

[0467]

[0468]

[0469] Table C3-4

[0470]

[0471]

[0472]

[0473] Table C3-5

[0474]

[0475]

[0476]

[0477]

[0478] Example C4 - Targeting *Glomerella lagenarium*, also known as cucurbit anthracnose fungus. (Colletotrichumlagenarium) (anthrax) fungicidal activity:

[0479] Frozen-stored fungal conidia were directly mixed into nutrient broth (PDB potato dextrose broth). A DMSO solution of the test compound was placed in a microtiter plate (96-well size), and nutrient broth containing the fungal conidia was added. These test plates were incubated at 24°C, and the inhibition of growth was determined spectrophotometrically at 620 nm after 72 hours.

[0480] When compared with an untreated control exhibiting extensive disease development under the same conditions, the following compound mixtures provided at least 80% control against Glomerella lagenarium at the ratios listed in the table:

[0481] Table C4-1 - For Glomerella lagenarium Antifungal activity > 80% (untreated %)

[0482]

[0483]

[0484]

[0485] Table C4-2 - For Glomerella lagenarium Antifungal activity > 80% (untreated %)

[0486]

[0487]

[0488]

[0489]

[0490]

[0491]

[0492] In the test ( Glomerella lagenarium, also known as cucurbit anthracnose fungus. (Colletotrichum lagenarium) In this study, the following mixture compositions are given as disease control at the concentrations (in ppm) reported in Tables C4-3 and C4-4. Fungicidal activity is evaluated on a 100-0 scale (100 = no disease growth; 0 = complete mycelial coverage).

[0493] Table C4-3

[0494]

[0495]

[0496]

[0497]

[0498] Table C4-4

[0499]

[0500]

[0501]

[0502] Example C5 - Fungicidal activity against *Cyclocarya multiflora* (target leaf spot disease).

[0503] Fungal conidia from frozen storage were directly mixed into nutrient broth (PDB potato dextrose broth). A DMSO solution of the test compound was placed in a microtiter plate (96-well size), and nutrient broth containing fungal conidia was added. These test plates were incubated at 24°C, and the inhibition of growth was determined spectrophotometrically at 620 nm after 3–4 days.

[0504] In this test (Cyclocarya multiflora), the following mixture compositions provided the following disease control at the concentrations (in ppm) reported in Tables C4-3 and C4-4. Fungicidal activity was evaluated on a 100-0 scale (100 = no disease growth; 0 = complete mycelial coverage).

[0505] Table C5-1

[0506]

[0507]

[0508]

[0509] Example D: Preventive activity against rust fungi in the soybean pod layer

[0510] Four weeks after planting, whole soybean plants were treated with the described active ingredient. One day after spraying, leaf discs were cut from the first leaf with three leaves. Five replicates were performed at each ratio. One day after treatment, the leaf discs were inoculated with *Soybean rust* (Asian soybean rust). The leaf discs were evaluated 11 to 14 days after inoculation, and the activity was derived from the infection test between the treated and untreated plants (100 = no disease, no leaf damage; 0 = highly infected, severe leaf damage). The ratio of active ingredient used is given in g active ingredient (ai) / ha in the table.

[0511] The results are shown in the table below:

[0512] Table D1 - Activity against *Pseudomonas aeruginosa* rust fungus (%) of untreated fungi

[0513]

[0514] Table D2 - Activity against *Pseudomonas aeruginosa* rust fungus (% of untreated)

[0515]

[0516]

[0517] Table D3 - Activity against *Pseudomonas aeruginosa* rust fungus (% of untreated)

[0518]

[0519] Table D4 - Activity against *Pseudomonas aeruginosa* rust fungus (% of untreated)

[0520]

[0521]

[0522] Table D5 - Activity against *Pseudomonas aeruginosa* rust fungus (untreated %)

[0523]

[0524] Table D6 - Activity against *Pseudomonas aeruginosa* rust fungus (% of untreated)

[0525]

[0526] Table D7 - Activity against *Pseudomonas aeruginosa* rust fungus (% of untreated)

[0527]

[0528]

[0529] Table D8 - Activity against *Pseudomonas aeruginosa* rust fungus (% of untreated)

[0530]

[0531] Table D9 - Activity against *Pseudomonas aeruginosa* rust fungus (% of untreated)

[0532]

[0533] Table D10 - Activity against *Pseudomonas aeruginosa* rust fungus (% of untreated)

[0534]

[0535] Table D11 - Activity against *Pseudomonas aeruginosa* rust fungus (untreated %)

[0536]

[0537] Table D12 - Activity against *Pseudomonas aeruginosa* rust fungus (% of untreated)

[0538]

[0539]

[0540] Table D13 - Activity against *Pseudomonas aeruginosa* rust fungus (% of untreated)

[0541]

[0542] Table D14 - Activity against *Pseudomonas bean* rust fungus (% of untreated)

[0543]

[0544]

[0545] Table D15 - Activity against *Pseudomonas aeruginosa* rust fungus (untreated %)

[0546]

[0547] Table D16 - Activity against *Phaseolus rust* (untreated %)

[0548]

[0549] Table D17 - Activity against *Pseudomonas aeruginosa* rust fungus (% of untreated)

[0550]

[0551]

[0552] Table D18 - Activity against rust fungi in the potato bean layer (%)

[0553]

[0554] Table D19 - Activity against *Pseudomonas aeruginosa* rust fungi (% of untreated)

[0555]

[0556]

[0557] Table D20 - Activity against rust fungi in the potato bean layer (%)

[0558]

[0559] Table D21 - Activity against *Potato Bean* Rust Fungus (%) (Untreated)

[0560]

[0561]

[0562] Table D22 - Activity against rust fungi in the potato bean layer (%)

[0563]

[0564] Table D23 - Activity against rust fungi in the potato bean layer (%)

[0565]

[0566]

[0567] Table D24 - Activity against rust fungi in the potato bean layer (%)

[0568]

[0569] Table D25 - Activity against rust fungi in the potato bean layer (%)

[0570]

[0571] Table D26 - Activity against rust fungi in the potato bean layer (%)

[0572]

[0573]

[0574] Table D27 - Activity against rust fungi in the potato bean layer (%)

[0575]

Claims

1. A fungicidal composition comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is: (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester, or (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxy-prop-2-enoic acid methyl ester; and Component (B) is a compound selected from N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide or [(1S,2S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(4-methoxy-3-propanoyloxy-pyridine-2-carbonyl)amino]propionate. in, The weight ratio of component (A) to component (B) is from 100:1 to 1:

100.

2. The antifungal composition according to claim 1, wherein, The weight ratio of component (A) to component (B) ranges from 20:1 to 1:

40.

3. The antifungal composition according to claim 1, wherein, The weight ratio of component (A) to component (B) ranges from 12:1 to 1:

25.

4. The antifungal composition according to claim 1, wherein, The weight ratio of component (A) to component (B) is from 5:1 and 1:

15.

5. The antifungal composition according to claim 1, wherein, The weight ratio of component (A) to component (B) ranges from 2:1 to 1:

5.

6. The antifungal composition according to claim 1, wherein, The composition comprises one or more additional pest control agents selected from the group consisting of: The fungicide, wherein the fungicide is selected from tebuconazole, fluazinam, benzovindiflubenzuron, fluopyram, benzalkonium chloride, benzalkonium chloride-M, furazolidone, metalaxyl, metalaxyl-M, doxycycline, N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidin, N'-[4-(4,5-dichloro-thiazol-2-yloxy)-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidin, N'-[4-[[3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl]oxy]-2,5-dimethyl-phenyl]- N-Ethyl-N-methylformamidin, Ethioprine, 3'-Chloro-2-methoxy-N-[(3RS)-tetrahydro-2-oxofuran-3-yl]acetyl-2',6'-dimethylaniline, Azoxystrobin, Azoxystrobin, Pyrimethanil, Dithionol, Nystatin Aureobasidium, Pyrimethanil-S, Biphenyl, Dimethomorph, Chlornitrifying Ammonium Chloride, Hexachlorobenzene, Pentachloronitrobenzene, Tetrachloronitrobenzene, Methyl Phosphate, Benzophenone, 2,6-Dichloro-N-(4-trifluoromethylbenzyl)-Benzamide, Fluopyram, Thiocyanamide, Sulfocarbamide, Benzopyr, Carbendazim, Carbendazim Hydrochloride, Chlorfenapyr, Wheat-Spinazole, Thiamethoxam Benzimidazole, Thiophanate-methyl, Benzylthiamethoxam, Mefenoxam, Thiamethoxam, Aramaic acid benzyl, Virkon, Methoxyfenozide, Aramaic acid benzyl-S-methyl, Pyraclostrobin, Butylamine, 3-Iodo-2-propynyl n-butylcarbamate, Iodopropynyl butylcarbamate, Isopropyl butylcarbamate, Tetraazolidinyl pyrrolidone, Polycarbamate, Cymoxanil, Trifluoromethoxycarbamate, 3-(difluoromethyl)-N-(7-fluoro-1,1,3,3-tetramethyl-indan-4-yl)-1-methyl-pyrazole-4-carboxamide, Dichlorophenoxyacetic acid, N-[(5-chloro-2-isopropyl-phenyl)methyl [N-Cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methylpyrazole-4-carboxamide, N-Cyclopropyl-3-(difluoromethyl)-5-fluoro-N-[(2-isopropylphenyl)methyl]-1-methylpyrazole-4-carboxamide, Cyclopropionylamine, Chlorothalonil, Fluoromorph, Quinoline Copper, Cymoxanil, Cyazofamid, Cyazofamid, Fluoxetine, Thiamethoxam, Ethiophanate-methyl, Iprodione, Procymidone, Nonglifen, Butyrimidine Sulfonate, Omdimethalin, Ammonium Nitrate, Acaricide, Acaricide, Diphenylamine, Chlorpyrifos, 2,6-Dimethyl-[1,4]dithiazoline[2,3-c: 5,6-c']dipyrrole-1,3,5,7(2H,6H)-Tetraketone, Thiram, Mancozeb, Ferrous Sulfate, Mancozeb, Mancozeb, Mancozeb, Mancozeb-Zinc, Sodium Mancozeb, Methyl Mancozeb, Thiram, Sodium Thiamethoxam, Mancozeb, Zinc Mancozeb, Dimethyl Disulfide, Isoprothiolane, Thiazolamide, Triethylphosphonic Acid, Aluminum Triethylphosphonate, Methyl Bromomethyl, Iodomethyl, Methyl Isothiocyanate, Cyclomethrin, Mefenoxam, Validamycin, Streptomycin, (2RS)-2-Bromo-2-(Bromomethyl)glutaronitrile, Polyfop-methyl, Dodecyl Guanidine Acetate, Biguanidine Octyl Salt, Biguanidine Octylamine, Biguanidine Octylamine Triacetate, 2,4-D, 2,4-DB, Kasugamycin, Mefenoxam, Cyclomethrin, Hymexazol, Sodium Chlorpyrifos, Imazalil, Imazalil Sulfate, Oxadiazol, Isoprothiolane, Prochloraz, Fluopyram Imidacloprid, Bordeaux mixture, calcium polysulfide, copper acetate, copper carbonate, copper hydroxide, copper naphthenate, copper oleate, copper oxychloride, copper hydroxyquinoline, copper silicate, copper sulfate, copper tallow, cuprous oxide, sulfur, carbaryl, isoprothiolane, pyridaben, fluoxetine, fluoxetine, dimethomorph, KSF-1002, phytoalexin, dimethomorph, butylmorpholine, tridemorpholine, dodecylmorpholine, ethoxysulfuron, triphenyltin acetate, triphenyltin hydroxide, carbendazim, oxycarbendazim, oxadiazon, m-phenylphenol, p-phenylphenol, tribromophenol, 2-[2-[(7,8-difluoro-2-methyl-3-quinolinyl)oxy]-6-fluoro-phenyl]propane-2-ol, 2-[2-fluoro-6-[(8-fluoro- 2-Methyl-3-quinolinyl)oxy]phenyl]propane-2-ol, cycloflufenicol, furazolidone, oxadixyl, fluopyram, cymoxanil, isothiazine, seed dressing pyrethroid, fludioxonil, pendimethalin, cyproconazole, isopyram, dimethoate, phosphoric acid, chlorothalonil, captan, chlormequat chloride, phosmet, benzoyl peroxide, benzoyl peroxide, oxadixyl, 1-methylcyclopropene, 4-CPA, chlormequat chloride, benzoylpyridinic acid, 2,4-D propionic acid, thiamethoxam, cymoxanil, ethephon, fludioxonil, chlorpyrifos, gibberellic acid, gibberellic acid, hymexazol, maleic hydrazine, phytohexidine, naphthylacetamide, paclobutrazol, cyclohexane, cyclohexane calcium, thidiazuron, defoliant, anti-rot acid, uniconazole, α-naphthaleneacetic acid, polyoxin D, BLAD, chitosan, cyanamide, captan 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichlorophenyl)ethyl]pyrazole-4-carboxamide, bifenthiophanate, fluopyram, furopyram, pyrazolenaphthylamine, pendimethalin, pyrimethanil, fluoxetine, pyridaben, pyridaben, pyridaben, pyridaben, pyridaben, fluopyram, diflubenzuron, chloropyrimidinol, 5-fluoro-2-(p-tolylmethoxy)pyrimidin-4-amine, pyrimethanil, sclerotinib, quinolones, propoxyquin, ethoxyquin, quinoxaline, 4,4,5-trifluoro-3,3-dimethyl-1-(3-quinolinyl)isoquinoline, 4,4-difluoro-3,3-dimethyl-1-(3-quinolinyl)isoquinoline, 5-fluoro-3,3,4,4-Tetramethyl-1-(3-quinolinyl)isoquinoline, 9-fluoro-2,2-dimethyl-5-(3-quinolinyl)-3H-1,4-benzoxazine, isobutylethoxyquinoline, oxaflutole, pyraclostrobin, pyraclostrobin, pyraclostrobin, pyraclostrobin, fluopyram, fluopyram, pyraclostrobin, mandesbin, fenoxybenzoamide, pyraclostrobin, pyraclostrobin, pyraclostrobin, pyraclostrobin, pyraclostrobin, pyraclostrobin, pyraclostrobin, mandesbin, pyraclostrobin, pyraclostrobin, pyraclostrobin, pyraclostrobin, pyraclostrobin, pyraclostrobin, pyraclostrobin, pyraclostrobin, pyraclostrobin, indazole, pyraclostrobin, pyraclostrobin, indazole, pyraclostrobin, pyraclostrobin, indazole, pyraclostrobin, pyraclostrobin, indazole, pyraclostrobin, pyraclostrobin, pyraclostrobin 6-[[(Z)-[(1-methyltetrazole-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate, dazomet, isothiazamide, thiamethoxam, thifluzamide, benzylthiocyanate, thiosilazamide, benzylthiocyanate, antifungal agent, tricyclazole, (.+-.)-cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol, 1-(5-bromo-2-pyridyl)-2-(2,4-difluorophenyl)-1,1-difluoro-3-(1,2,4-triazol-1-yl)propane-2-ol, 2-(1-tert-butyl)-1-(2-chlorophenyl)-3-(1,2,4-triazol-1-yl)-propane-2-ol , (N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidinium), azaconazole, bifenthrin, furazolidone, clomibazole, cycloconazole, difenoconazole, tebuconazole, tebuconazole-M, fluconazole, eticonazole, cyproconazole, fluquinazole, flusilazole, fenazol, hexaconazole, imidacloprid, tebuconazole, propiconazole, thiophanate-methyl, chlorfluazol, silfluazol, tebuconazole, tetraflufenazole, triadimefon, triadimefon, imidazolimide, tebuconazole, 2-[[(1R,5S)-5-[(4-fluorophenyl)methyl]-1-hydroxy-2,2-dimethyl-cyclopentyl] [Methyl]-4H-1,2,4-triazol-3-thione, 2-[[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)ethylene-2-yl]methyl]-4H-1,2,4-triazol-3-thione, azoxystrobin, isopropylamine, valproic acid, 2-benzyl-4-chlorophenol, allyl alcohol, pyrazosulfuron, benzalkonium chloride, chloropicrin, cresol, darasetrad, diclofenac, oat fumed meal, disulfiram, N-(2-p-chlorobenzoylethyl)-hexamethylenetetramine chloride, NNF-0721, octathione, pyrimisulfuron, plant extracts containing tea tree oil and Melaleuca alternifolia, biostimulants containing organic carbon, nutrients and amino acids, propanemidine and propionic acid; or, Insecticides, wherein the insecticides are selected from abamectin, chlorpyrifos, acetamiprid, sulfadiazine, abamectin, azadirachtin, methyl glutathione, bifenthrin, bifenazate, brofenoxam, thiamethoxam, carbofuran, batan, chlorantraniliprole, brofenoxam, flufenoxuron, chlorpyrifos, methyl chlorpyrifos, cyclone dichlorvos, thiamethoxam, diflubenzuron, lambda-cyhalothrin, β-cyhalothrin, deltamethrin, and λ. -Cypermethrin, cypermethrin, cyromazine, deltamethrin, difenoconazole, diazinon, dieldrin, diflubenzuron, tetramethrin, dimethoate, fipronil, benzyl ether, emamectin, endosulfan, cypermethrin, acetamiprid, benzyl thiocarb, fenoxycarb, cypermethrin, fenvalerate, flufenoxuron, flufenoxuron, flufenoxuron, t-flufenoxuron, pyrimethanil, flufenoxuron, terbufos, chlorfenapyr Hydrazine, Flufenoxuron, Flufenoxuron, Imidacloprid, Indoxacarb, Isofenphos, Lufenuron, Malathion, Cyfluthrin, Methaldehyde, Methamidophos, Chlorpyrifos, Dimethoate, Acetaminophen, Methoxychloride, Methoxyfenozide, Monocrotophos, Methoxyfenozide, Acetaminophen, Niethoxysulfuron, Diflubenzuron, Parathion, Methyl Parathion, Permethrin, Phosphate, Phosphamidon, Phosphamidon, Phosphamidon, Apicarb, Propiconium Chloride, Pyriproxyfenozide Bromophos, propofol, pymetrozine, pyrethroid, acetamiprid, flufenoxuron, pyrazosulfuron, fenpropathrin, rotenone, linanodin, spinosad, spinosad, spirodiclofen, spirotetramat, thiophanate-methyl, tebufenozide, flufenoxuron, heptafluthrin, terbufos, carbendazim, thiamethoxam, thiamethoxam, thiamethoxam, chlorpyrifos, tetramethrin, pymetrozine, trichlorfon, and chlorpyrifos; or Bactericide, wherein the bactericide is selected from streptomycin; or Acaricides, wherein the acaricides are selected from amitraz, dicofol, ethyl chlorpyrifos, cypermethrin, tricyclic tin, trichlorfon, chlorpyrifos, etoxazole, quinclorac, fenbutatin, cypermethrin, azoxystrobin, thiamethoxam, dicofol, pyridaben, and pyridaben; or Biological reagents, wherein the biological reagents are selected from Bacillus thuringiensis, Bacillus thuringiensis δ-endotoxin, baculoviruses, insect pathogenic bacteria, viruses, and fungi.

7. The antifungal composition according to claim 1, wherein, The composition further comprises an agriculturally acceptable carrier, and optionally a surfactant and / or formulation aid.

8. A method for controlling or preventing plant pathogenic diseases, particularly plant pathogenic fungi, on useful plants or their propagation material, the method comprising applying a fungicidal composition as defined in any one of claims 1 to 7 to the useful plant, its location, or its propagation material.

9. The method according to claim 8, wherein the composition components (A) and (B) are applied in a sequential manner.

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