RU2833878C1 - Fungicidal compositions - Google Patents

Abstract

FIELD: agriculture.

SUBSTANCE: invention relates to agriculture, in particular to plant protection agents. Fungicidal composition contains a mixture of components (A) and (B) as active ingredients, where component (A) is: methyl-(Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxyprop-2-enoate or methyl-(Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxyprop-2-enoate or its agronomically acceptable salt and component (B) is a compound selected from the group consisting of bixaphene, copper hydroxide, acibenzolar-S-methyl, copper oxychloride, cyproconazole, difenoconazole, epoxiconazole, flutriafol, hexaconazole, metconazole, paclobutrazole, prothioconazole, propiconazole, tebuconazole, fenpropidine, fenpropimorph, fludioxonil, azoxystrobin, dimoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, mancozeb, folpeta, chlorothalonil, fluazinam, fluxapiroxade, isopyrazam, sedaxane, benzovindiflupir, pidiflumethofen, isoflucipram, fluindapyr, inpyrfluxam, mefentrifluconazole, aminopyrifene, florylpicoxamide, fenpicoxamide, ipflufenoquine, quinofumelin, fluopyram, methyltetraprole, trinexapac, trinexapac-ethyl, 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]cyclopropane carboxamide, N,2-dimethoxy-n-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, [(1S,2S)-1-methyl-2-(o-tolyl)propyl]-(2S)-2-[(4-methoxy-3-propanoyloxypyridine-2-carbonyl)amino]propanoate, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, and (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N, 3-dimethylpent-3-enamide. Weight ratio of component (A) and component (B) ranges from 100:1 to 1:100. Method of controlling phytopathogenic diseases of useful plants or their propagation material caused by phytopathogenic fungi, involves application of fungicidal composition with respect to useful plants, their place of growth or their propagation material. Fungicidal composition is also used to prevent phytopathogenic diseases of useful plants or their propagation material caused by phytopathogenic fungi.

EFFECT: disclosed fungicidal composition extends the range of fungicidal protection of plants, has accelerated action, does not cause resistance, reduces consumption of active substances.

13 cl, 49 tbl, 12 ex

Description

The present invention relates to new fungicidal compositions, to their use in agriculture or plant growing for the control of diseases caused by phytopathogens, especially phytopathogenic fungi, and to methods for the control of diseases of useful plants.

While many fungicidal compounds and compositions belonging to various different chemical classes have been/are being developed for use as fungicides in crops of useful plants, the tolerance of crops and activity against certain phytopathogenic fungi do not always meet the needs of agricultural practice in many respects. Therefore, there is a constant need to find new compounds and compositions characterized by superior biological properties for use in controlling or preventing plant infestation by phytopathogenic fungi. For example, compounds with higher biological activity, a preferable spectrum of activity, an increased safety profile, improved physicochemical properties, increased biodegradability. Or in other words, compositions that have a broader spectrum of activity, improved crop tolerance, synergistic interactions or potentiating properties, or compositions that exhibit a faster onset of action or that are characterized by a longer residual activity, or that provide for a reduction in the number of applications and/or a reduction in the application rate of the compounds and compositions required to effectively control the phytopathogen, thereby providing for preferential sustainability management practices, reduced environmental impact and reduced operator exposure.

The use of compositions containing mixtures of different fungicidal compounds with different modes of action may meet some of these needs (e.g. by combining fungicides with different spectra of activity).

According to the present invention, there is provided a fungicidal composition comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is a compound of formula (I):

Where

R ¹ is methyl;

R ² is hydrogen;

R ³ is hydrogen;

is _C3 - _C7 cycloalkyl;

or its agronomically acceptable salt,

And

component (B) is a compound selected from the group consisting of

bixafen, sulfur, copper hydroxide, triclopyricarb, acibenzolar-b-methyl, copper oxychloride, cyproconazole, difenoconazole, epoxiconazole, flutriafol, hexaconazole, ipconazole, metconazole, paclobutrazol, prothioconazole, prochloraz, propiconazole, pyrisoxazole, tebuconazole, fenpropidin, fenpropimorph, spiroxamine, cyprodinil, fludioxonil, metalaxyl, metalaxyl-M (mefenoxam), carbendazim, penthiopyrad, azoxystrobin, dimoxystrobin, phenaminestrobin, flufenoxystrobin, fluoxastrobin, metominostrobin, trifloxystrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, mancozeb, folpet, chlorothalonil, fluazinam, fluxapyroxad, fenhexamide, fosetyl aluminum, pyribencarb, tricyclazole, mandipropamide, flubeneteram, isopyrazam, sedaxan, benzovindiflupyr, pydiflumetofen, isoflucipram, isothianil, dipimethitrone, fluindapyr, cumethoxystrobin (jiaxiangjunzhi), luebengymixianan, mandestrobin, oxathiapiproline, pyraziflumide, inpirfluxam, mefentrifluconazole, ipfentrifluconazole, aminopyrifene, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethylpent-3-enamide, florylpicoxamide, fenpicoxamide, ipflufenoquine, quinofumelin, benzothiostrobin, fluopyram, pyrapropone, 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethylindan-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, methyltetraprole, fluoxapiproline, enoxastrobin, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, trinexapac, trinexapac-ethyl, kumoxystrobin, N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxyethoxy]-3-pyridyl]-N-ethyl-N-methylformamidine, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxyethoxy]-3-pyridyl]-N-ethyl-N-methylformamidine, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxyethoxy)-3-pyridyl]-N-ethyl-N-methylformamidine, N'-[5-chloro-2-methyl-6-(1-methyl-2-propoxyethoxy)-3-pyridyl]-N-ethyl-N-methylformamidine, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxyethoxy)-3-pyridyl]-N-isopropyl-N-methylformamidine, N'-[5-bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N-methylformamidine, N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenylethyl)phenyl]-N-methylformamidine, N'-[4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxyethyl)-5-methoxy-2-methylphenyl]-N-isopropyl-N-methylformamidine, N-ethyl-N'-[5-methoxy-2-methyl-4-[2-trifluoromethyl)oxetan-2-yl]phenyl]-N-methylformamidine, N-ethyl-N'-[5-methoxy-2-methyl-4-[2-trifluoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methylformamidine, 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]cyclopropanecarboxamide, N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, [(1S,2S)-1-methyl-2-(o-tolyl)propyl]-(2S)-2-[(4-methoxy-3-propanoyloxypyridine-2-carbonyl)amino]propanoate, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylate, 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)propan-2-ol, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile, 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile, (4-phenoxyphenyl)methyl-2-amino-6-methylpyridin-3-carboxylate, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide; 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-dimethylpent-3-enamide, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone, (3-methyl-isoxazol-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone, ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide, N-[(7)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, N-[N-methoxy-C-methylcarbonimidoyl]-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)-H-(1,1-dimethyl-3-propylindan-4-yl)pyridin-3-carboxamide, [(1S,2S)-2-(4-fluoro-2-methylphenyl)-1,3-dimethylbutyl]-(2S)-2-[(3-acetoxy-4-methoxypyridine-2-carbonyl)amino]propanoate, [(1S,2S)-2-(4-fluoro-2-methylphenyl)-1,3-dimethylbutyl]-(2S)-2-[[3-(acetoxymethoxy)-4-methoxypyridine-2-carbonyl]amino]propanoate, 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, dichlorprop, diglycolamine, dimethylamine, dimethylammonium, potassium and sodium), glufosinate (including its ammonium salts), thiamethoxam, cyclobutrifluram, isocycloseram, spiropidion, abamectin, emamectin, cyantraniliprole, chlorantraniliprole, diafenthiuron, 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 fluxamethamide.

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

Additionally, according to the present invention, there is provided a method for controlling or preventing phytopathogenic diseases of useful plants or their propagation material, especially those caused by phytopathogenic fungi, which involves using a fungicidal composition according to the present invention with respect to useful plants, their growing place or their propagation material.

The advantages provided by certain fungicidal mixture compositions according to the present invention may also include, inter alia, preferable levels of biological activity for protecting plants from diseases caused by fungi, or superior properties for use as agrochemical active ingredients (e.g. higher biological activity, preferable spectrum of activity, improved safety profile, improved physicochemical properties or increased biodegradability).

Preferred groups and meanings of substituents R ¹ , R ² , R ³ and R ⁴ in the compounds of formula (I) in any combination thereof are given below.

R ¹ is methyl.

R ² is hydrogen.

R ³ is hydrogen.

R ⁴ is C ₃ -C ₇ cycloalkyl.

Preferably, component (A) is a compound selected from methyl (Z)-2-(5-cyclobutyl-2-methylphenoxy)-3-methoxyprop-2-enoate (compound X.01),

methyl-(Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxyprop-2-enoate (compound X.02),

methyl (Z)-2-(5-cyclopropyl-2-methylphenoxy)-3-methoxyprop-2-enoate (compound X.03) or

methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxyprop-2-enoate (compound X.04), as defined in Table X below.

More preferably, component (A) is a compound selected from methyl (Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxyprop-2-enoate (compound X.02) or

methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxyprop-2-enoate (compound X.04), as defined in Table X below.

In one embodiment, component (A) is methyl (Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxyprop-2-enoate (compound X.02).

In another embodiment, component (A) is methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxyprop-2-enoate (compound X.04).

Component (B) is a compound selected from the group consisting of

bixafen, sulfur, copper hydroxide, triclopyricarb, acibenzolar-S-methyl, copper oxychloride, cyproconazole, difenoconazole, epoxiconazole, flutriafol, hexaconazole, ipconazole, metconazole, paclobutrazol, prothioconazole, prochloraz, propiconazole, pyrisoxazole, tebuconazole, fenpropidin, fenpropimorph, spiroxamine, cyprodinil, fludioxonil, metalaxyl, metalaxyl-M (mefenoxam), carbendazim, penthiopyrad, azoxystrobin, dimoxystrobin, phenaminestrobin, flufenoxystrobin, fluoxastrobin, metominostrobin, trifloxystrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, mancozeb, folpet, chlorothalonil, fluazinam, fluxapyroxad, fenhexamide, fosetyl aluminum, pyribencarb, tricyclazole, mandipropamide, flubeneteram, isopyrazam, sedaxan, benzovindiflupyr, pydiflumetofen, isoflucipram, isothianil, dipimethitrone, fluindapyr, cumethoxystrobin (jiaxiangjunzhi), luebengymixianan, mandestrobin, oxathiapiproline, pyraziflumide, inpirfluxam, mefentrifluconazole, ipfentrifluconazole, aminopyrifene, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethylpent-3-enamide, florylpicoxamide, fenpicoxamide, ipflufenoquine, quinofumelin, benzothiostrobin, fluopyram, pyrapropone, 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethylindan-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, methyltetraprole, fluoxapiproline, enoxastrobin, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, trinexapac, trinexapac-ethyl, kumoxystrobin, N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxyethoxy]-3-pyridyl]-N-ethyl-N-methylformamidine, N-[5-bromo-2-methyl-6-[(1H)-1-methyl-2-propoxyethoxy]-3-pyridyl]-N-ethyl-N-methylformamidine, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxyethoxy)-3-pyridyl]-N-ethyl-N-methylformamidine, N'-[5-chloro-2-methyl-6-(1-methyl-2-propoxyethoxy)-3-pyridyl]-N-ethyl-N-methylformamidine, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxyethoxy)-3-pyridyl]-N-isopropyl-N-methylformamidine, N'-[5-bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N-methylformamidine, N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenylethyl)phenyl]-N-methylformamidine, N'-[4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxyethyl)-5-methoxy-2-methylphenyl]-N-isopropyl-N-methylformamidine, N-ethyl-N'-[5-methoxy-2-methyl-4-[2-trifluoromethyl)oxetan-2-yl]phenyl]-N-methylformamidine, N-ethyl-N'-[5-methoxy-2-methyl-4-[2-trifluoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methylformamidine, 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]cyclopropanecarboxamide, N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, N-ethyl 2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, [(1S,2S)-1-methyl-2-(o-tolyl)propyl]-(2S)-2-[(4-methoxy-3-propanoyloxypyridine-2-carbonyl)amino]propanoate, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylate, 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)propan-2-ol, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile, 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile, (4-phenoxyphenyl)methyl-2-amino-6-methylpyridine-3-carboxylate, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide; 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-dimethylpent-3-enamide, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone, (3-methyl-isoxazol-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone, ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide, N-[(7)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, N-[N-methoxy-C-methylcarbonimidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, N-[3-(4-chlorophenyl)-4,5-dihydroisoxazol-5-yl]-5-methyl-1,2,4-oxadiazole-3-carboxamide, 2-(difluoromethyl)-N-(1,1-dimethyl-3-propylindan-4-yl)pyridine-3-carboxamide, [(1S,2S)-2-(4-fluoro-2-methylphenyl)-1,3-dimethylbutyl]-(2S)-2-[(3-acetoxy-4-methoxypyridine-2-carbonyl)amino]propanoate, [(1S,2S)-2-(4-fluoro-2-methylphenyl)-1,3-dimethylbutyl]-(2S)-2-[[3-(acetoxymethoxy)-4-methoxypyridine-2-carbonyl]amino]propanoate, 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, dichlorprop, diglycolamine, dimethylamine, dimethylammonium, potassium and sodium), glufosinate (including its ammonium salts), thiamethoxam, cyclobutrifluram, isocycloseram, spiropidion, abamectin, emamectin, cyantraniliprole, chlorantraniliprole, diafenthiuron, 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 fluxamethamide.

Preferably, component B is a compound selected from the group consisting of bixafen, sulfur, copper hydroxide, triclopyricarb, acibenzolar-S-methyl, copper oxychloride, cyproconazole, difenoconazole, epoxiconazole, flutriafol, hexaconazole, ipconazole, metconazole, paclobutrazol, prothioconazole, prochloraz, propiconazole, pyrisoxazole, tebuconazole, fenpropidin, fenpropimorph, spiroxamine, cyprodinil, fludioxonil, metalaxyl, metalaxyl-M (mefenoxam), carbendazim, penthiopyrad, azoxystrobin, dimoxystrobin, phenaminestrobin, flufenoxystrobin, fluoxastrobin, Metominostrobin, trifloxystrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, mancozeb, folpet, chlorothalonil, fluazinam, fluxapyroxad, fenhexamide, fosetyl aluminum, pyribencarb, tricyclazole, mandipropamide, flubeneteram, isopyrazam, sedaxan, benzovindiflupyr, pidiflumetofen, isoflucipram, isothianil, dipimethitrone, fluindapyr, cumethoxystrobin (jiaxiangjunzhi), lubenymixianan, mandestrobin, oxathiapiproline, pyraziflumide, inpirfluxam, mefentrifluconazole, ipfentrifluconazole, aminopyrifene, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethylpent-3-enamide, florylpicoxamide, fenpicoxamide, ipflufenoquine, quinofumelin, benzothiostrobin, fluopyram, pyrapropone, 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethylindan-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, methyltetraprole, fluoxapiproline, enoxastrobin, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, trinexapac, trinexapac-ethyl, kumoxystrobin, N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxyethoxy]-3-pyridyl]-N-ethyl-N-methylformamidine, N'-[5-bromo-2-methyl-6-[(1H)-1-methyl-2-propoxyethoxy]-3-pyridyl]-N-ethyl-N-methylformamidine, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxyethoxy)-3-pyridyl]-N-ethyl-N-methylformamidine, N'-[5-chloro-2-methyl-6-(1-methyl-2-propoxyethoxy)-3-pyridyl]-N-ethyl-N-methylformamidine, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxyethoxy)-3-pyridyl]-N-isopropyl-N-methylformamidine, N'-[5-bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N-methylformamidine, N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenylethyl)phenyl]-N-methylformamidine, N'-[4-(1-cyutopropyl-2,2,2-trifluoro-1-hydroxyethyl)-5-methoxy-2-methylphenyl]-N-isopropyl-N-methylformamidine, N-ethyl-N'-[5-methoxy-2-methyl-4-[2-trifluoromethyl)oxetan-2-yl]phenyl]-N-methylformamidine, N-ethyl-N'-[5-methoxy-2-methyl-4-[2-trifluoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methylformamidine, 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]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylate, 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)propan-2-ol, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile, 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile, (4-phenoxyphenyl)methyl-2-amino-6-methylpyridine-3-carboxylate, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide; 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-dimethylpent-3-enamide, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone, (3-methylisoxazol-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone, ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate, 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-methylcarbonimidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, N-[3-(4-chlorophenyl)-4,5-dihydroisoxazol-5-yl]-5-methyl-1,2,4-oxadiazole-3-carboxamide, 2-(difluoromethyl)-N-(1,1-dimethyl-3-propylindan-4-yl)pyridine-3-carboxamide, [(1S,2S)-2-(4-fluoro-2-methylphenyl)-1,3-dimethylbutyl]-(2S)-2-[(3-acetoxy-4-methoxypyridine-2-carbonyl)amino]propanoate, [(1S,2S)-2-(4-fluoro-2-methylphenyl)-1,3-dimethylbutyl]-(2S)-2-[[3-(acetoxymethoxy)-4-methoxypyridine-2-carbonyl]amino]propanoate, 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, dichlorprop, diglycolamine, dimethylamine, dimethylammonium, potassium and sodium), glufosinate (including its ammonium salts), thiamethoxam, cyclobutrifluram, isocycloseram, spiropidion, abamectin, emamectin, cyantraniliprole, chlorantraniliprole, diafenthiuron, 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 fluxamethamide.

More preferably, component (B) is a compound selected from the group consisting of bixafen, triclopiricarb, cyproconazole, difenoconazole, epoxiconazole, flutriafol, hexaconazole, ipconazole, metconazole, prothioconazole, propiconazole, tebuconazole, azoxystrobin, dimoxystrobin, phenaminestrobin, flufenoxystrobin, fluoxastrobin, metominostrobin, trifloxystrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, mancozeb, chlorothalonil, fluxapyroxade, pyribencarb, benzovindiflupyr, isoflucipram, cumethoxystrobin (jiaxiangjunzhi), mandestrobin, mefentrifluconazole, ipfentrifluconazole, benzothiostrobin, methyltetraprole, enoxastrobin, coumoxystrobin, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile and 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile.

Even more preferably, component (B) is a compound selected from the group consisting of cyproconazole, difenoconazole, hexaconazole, prothioconazole, propiconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, mancozeb, chlorothalonil, fluxapyroxade, benzovindiflupyr, isoflucipram and methyltetraprole.

Moreover, component (B) is even more preferably a compound selected from the group consisting of cyproconazole, difenoconazole, hexaconazole, prothioconazole, propiconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin and methyltetraprole.

Even more preferably, component (B) is a compound selected from the group consisting of cyproconazole, difenoconazole, prothioconazole, azoxystrobin, trifloxystrobin, pyraclostrobin and methyltetraprole.

In this case, component (B) is even more preferably azoxystrobin or trifloxystrobin.

Most preferably, component (B) is azoxystrobin.

In one embodiment, component (B) is a compound selected from the group consisting of cyproconazole, difenoconazole, hexaconazole, prothioconazole, propiconazole, fenpropidin, fenpropimorph, fludioxonil, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, mancozeb, folpet, chlorothalonil, fluxapyroxade, benzovindiflupyr, isoflucipram, pydiflumetofen, mefentrifluconazole, florylpicoxamide, methyltetraprole, 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-propanoyloxypyridine-2-carbonyl)amino]propanoate. Preferably, component (B) is a compound selected from the group consisting of cyproconazole, difenoconazole, prothioconazole, fenpropidin, fenpropimorph, fludioxonil, azoxystrobin, trifloxystrobin, pyraclostrobin, mancozeb, folpet, chlorothalonil, benzovindiflupyr, pydiflumetofen, mefentrifluconazole, florylpicoxamide, methyltetraprole, 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-propanoyloxypyridine-2-carbonyl)amino]propanoate.

The compounds constituting component (B) are listed herein and above under the so-called "common name according to ISO" or other "common name" used in individual cases, or under a trade name. The compounds constituting component (B) are known and are commercially available and/or can be prepared using procedures known in the art and/or procedures described in the literature.

In a preferred composition according to the present invention, component (A) is the compound of No. X.01, methyl (Z)-2-(5-cyclobutyl-2-methylphenoxy)-3-methoxyprop-2-enoate, or a salt or tautomer thereof, and component (B) is a compound selected from the group consisting of bixafen, triclopyricarb, cyproconazole, difenoconazole, epoxiconazole, flutriafol, hexaconazole, ipconazole, metconazole, prothioconazole, propiconazole, tebuconazole, azoxystrobin, dimoxystrobin, phenaminestrobin, flufenoxystrobin, fluoxastrobin, metominostrobin, trifloxystrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyroxystrobin, mancozeb, chlorothalonil, fluxapyroxad, pyribencarb, benzovindiflupyr, isoflucipram, cumethoxystrobin (jiaxiangjunzhi), mandestrobin, mefentrifluconazole, ipfentrifluconazole, benzothiostrobin, methyltetraprole, enoxastrobin, coumoxystrobin, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile and 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile, wherein the weight ratio of component (A) and component (B) is from 15:1 to 1:50.

In another preferred composition according to the present invention, component (A) is the compound of No. X.02, methyl (Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxyprop-2-enoate, or a salt or tautomer thereof, and component (B) is a compound selected from the group consisting of bixafen, triclopyricarb, cyproconazole, difenoconazole, epoxiconazole, flutriafol, hexaconazole, ipconazole, metconazole, prothioconazole, propiconazole, tebuconazole, azoxystrobin, dimoxystrobin, phenaminestrobin, flufenoxystrobin, fluoxastrobin, metominostrobin, trifloxystrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyroxystrobin, mancozeb, chlorothalonil, fluxapyroxad, pyribencarb, benzovindiflupyr, isoflucipram, cumethoxystrobin (jiaxiangjunzhi), mandestrobin, mefentrifluconazole, ipfentrifluconazole, benzothiostrobin, methyltetraprole, enoxastrobin, coumoxystrobin, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile and 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile, wherein the weight ratio of component (A) and component (B) is from 15:1 to 1:50.

In another preferred composition according to the present invention, component (A) is the compound of No. X.03, methyl (Z)-2-(5-cyclopropyl-2-methylphenoxy)-3-methoxyprop-2-enoate, or a salt or tautomer thereof, and component (B) is a compound selected from the group consisting of bixafen, triclopyricarb, cyproconazole, difenoconazole, epoxiconazole, flutriafol, hexaconazole, ipconazole, metconazole, prothioconazole, propiconazole, tebuconazole, azoxystrobin, dimoxystrobin, phenaminestrobin, flufenoxystrobin, fluoxastrobin, metominostrobin, trifloxystrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyroxystrobin, mancozeb, chlorothalonil, fluxapyroxad, pyribencarb, benzovindiflupyr, isoflucipram, cumethoxystrobin (jiaxiangjunzhi), mandestrobin, mefentrifluconazole, ipfentrifluconazole, benzothiostrobin, methyltetraprole, enoxastrobin, coumoxystrobin, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile and 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile, wherein the weight ratio of component (A) and component (B) is from 15:1 to 1:50.

In another preferred composition according to the present invention, component (A) is the compound of No. X.04, methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxyprop-2-enoate, or a salt or tautomer thereof, and component (B) is a compound selected from the group consisting of bixafen, triclopiricarb, cyproconazole, difenoconazole, epoxiconazole, flutriafol, hexaconazole, ipconazole, metconazole, prothioconazole, propiconazole, tebuconazole, azoxystrobin, dimoxystrobin, phenaminestrobin, flufenoxystrobin, fluoxastrobin, metominostrobin, trifloxystrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyroxystrobin, mancozeb, chlorothalonil, fluxapyroxad, pyribencarb, benzovindiflupyr, isoflucipram, cumethoxystrobin (jiaxiangjunzhi), mandestrobin, mefentrifluconazole, ipfentrifluconazole, benzothiostrobin, methyltetraprole, enoxastrobin, coumoxystrobin, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile and 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile, wherein the weight ratio of component (A) and component (B) is from 15:1 to 1:50.

In a more preferred composition according to the present invention, component (A) is compound No. X.01, methyl (Z)-2-(5-cyclobutyl-2-methylphenoxy)-3-methoxyprop-2-enoate, or a salt or tautomer thereof, and component (B) is a compound selected from the group consisting of cyproconazole, difenoconazole, hexaconazole, prothioconazole, propiconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, mancozeb, chlorothalonil, fluxapyroxade, benzovindiflupyr, isoflucipram and methyltetraprole, wherein the weight ratio of component (A) to component (B) is from 15:1 to 1:50.

In a more preferred composition according to the present invention, component (A) is compound No. X.02, methyl (Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxyprop-2-enoate, or a salt or tautomer thereof, and component (B) is a compound selected from the group consisting of cyproconazole, difenoconazole, hexaconazole, prothioconazole, propiconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, mancozeb, chlorothalonil, fluxapyroxade, benzovindiflupyr, isoflucipram and methyltetraprole, wherein the weight ratio of component (A) to component (B) is from 15:1 to 1:50.

In a more preferred composition according to the present invention, component (A) is compound No. X.03, methyl (Z)-2-(5-cyclopropyl-2-methylphenoxy)-3-methoxyprop-2-enoate, or a salt or tautomer thereof, and component (B) is a compound selected from the group consisting of cyproconazole, difenoconazole, hexaconazole, prothioconazole, propiconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, mancozeb, chlorothalonil, fluxapyroxade, benzovindiflupyr, isoflucipram and methyltetraprole, wherein the weight ratio of component (A) to component (B) is from 15:1 to 1:50.

In a more preferred composition according to the present invention, component (A) is compound No. X.04, methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxyprop-2-enoate, or a salt or tautomer thereof, and component (B) is a compound selected from the group consisting of cyproconazole, difenoconazole, hexaconazole, prothioconazole, propiconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, mancozeb, chlorothalonil, fluxapyroxade, benzovindiflupyr, isoflucipram and methyltetraprole, wherein the weight ratio of component (A) to component (B) is from 15:1 to 1:50.

In a preferred composition according to the present invention, component (A) is the compound of No. X.01, methyl (Z)-2-(5-cyclobutyl-2-methylphenoxy)-3-methoxyprop-2-enoate, or a salt or tautomer thereof, and component (B) is a compound selected from the group consisting of bixafen, triclopyricarb, cyproconazole, difenoconazole, epoxiconazole, flutriafol, hexaconazole, ipconazole, metconazole, prothioconazole, propiconazole, tebuconazole, azoxystrobin, dimoxystrobin, phenaminestrobin, flufenoxystrobin, fluoxastrobin, metominostrobin, trifloxystrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyroxystrobin, mancozeb, chlorothalonil, fluxapyroxad, pyribencarb, benzovindiflupyr, isoflucipram, cumethoxystrobin (jiaxiangjunzhi), mandestrobin, mefentrifluconazole, ipfentrifluconazole, benzothiostrobin, methyltetraprole, enoxastrobin, coumoxystrobin, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile and 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile, wherein the weight ratio of component (A) to component (B) is from 10:1 to 1:10 (or even more preferably from 7.5:1 to 1:7.5).

In another preferred composition according to the present invention, component (A) is the compound of No. X.02, methyl (Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxyprop-2-enoate, or a salt or tautomer thereof, and component (B) is a compound selected from the group consisting of bixafen, triclopyricarb, cyproconazole, difenoconazole, epoxiconazole, flutriafol, hexaconazole, ipconazole, metconazole, prothioconazole, propiconazole, tebuconazole, azoxystrobin, dimoxystrobin, phenaminestrobin, flufenoxystrobin, fluoxastrobin, metominostrobin, trifloxystrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyroxystrobin, mancozeb, chlorothalonil, fluxapyroxad, pyribencarb, benzovindiflupyr, isoflucipram, cumethoxystrobin (jiaxiangjunzhi), mandestrobin, mefentrifluconazole, ipfentrifluconazole, benzothiostrobin, methyltetraprole, enoxastrobin, coumoxystrobin, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile and 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile, wherein the weight ratio of component (A) to component (B) is from 10:1 to 1:10 (or even more preferably from 7.5:1 to 1:7.5).

In another preferred composition according to the present invention, component (A) is the compound of No. X.03, methyl (Z)-2-(5-cyclopropyl-2-methylphenoxy)-3-methoxyprop-2-enoate, or a salt or tautomer thereof, and component (B) is a compound selected from the group consisting of bixafen, triclopyricarb, cyproconazole, difenoconazole, epoxiconazole, flutriafol, hexaconazole, ipconazole, metconazole, prothioconazole, propiconazole, tebuconazole, azoxystrobin, dimoxystrobin, phenaminestrobin, flufenoxystrobin, fluoxastrobin, metominostrobin, trifloxystrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyroxystrobin, mancozeb, chlorothalonil, fluxapyroxad, pyribencarb, benzovindiflupyr, isoflucipram, cumethoxystrobin (jiaxiangjunzhi), mandestrobin, mefentrifluconazole, ipfentrifluconazole, benzothiostrobin, methyltetraprole, enoxastrobin, coumoxystrobin, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile and 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile, wherein the weight ratio of component (A) to component (B) is from 10:1 to 1:10 (or even more preferably from 7.5:1 to 1:7.5).

In another preferred composition according to the present invention, component (A) is the compound of No. X.04, methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxyprop-2-enoate, or a salt or tautomer thereof, and component (B) is a compound selected from the group consisting of bixafen, triclopiricarb, cyproconazole, difenoconazole, epoxiconazole, flutriafol, hexaconazole, ipconazole, metconazole, prothioconazole, propiconazole, tebuconazole, azoxystrobin, dimoxystrobin, phenaminestrobin, flufenoxystrobin, fluoxastrobin, metominostrobin, trifloxystrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyroxystrobin, mancozeb, chlorothalonil, fluxapyroxad, pyribencarb, benzovindiflupyr, isoflucipram, cumethoxystrobin (jiaxiangjunzhi), mandestrobin, mefentrifluconazole, ipfentrifluconazole, benzothiostrobin, methyltetraprole, enoxastrobin, coumoxystrobin, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile and 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile, wherein the weight ratio of component (A) to component (B) is from 10:1 to 1:10 (or even more preferably from 7.5:1 to 1:7.5).

In a preferred composition according to the present invention, component (A) is compound No. X.01, methyl (Z)-2-(5-cyclobutyl-2-methylphenoxy)-3-methoxyprop-2-enoate, or a salt or tautomer thereof, and component (B) is a compound selected from the group consisting of cyproconazole, difenoconazole, hexaconazole, prothioconazole, propiconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, mancozeb, chlorothalonil, fluxapyroxade, benzovindiflupyr, isoflucipram and methyltetraprole, wherein the weight ratio of component (A) to component (B) is from 10:1 to 1:10 (or even more preferably from 7.5:1 to 1:7.5).

In another preferred composition according to the present invention, component (A) is compound No. X.02, methyl (Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxyprop-2-enoate, or a salt or tautomer thereof, and component (B) is a compound selected from the group consisting of cyproconazole, difenoconazole, hexaconazole, prothioconazole, propiconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, mancozeb, chlorothalonil, fluxapyroxade, benzovindiflupyr, isoflucipram and methyltetraprole, wherein the weight ratio of component (A) to component (B) is from 10:1 to 1:10 (or even more preferably from 7.5:1 to 1:7.5).

In another preferred composition according to the present invention, component (A) is compound No. X.03, methyl (Z)-2-(5-cyclopropyl-2-methylphenoxy)-3-methoxyprop-2-enoate, or a salt or tautomer thereof, and component (B) is a compound selected from the group consisting of cyproconazole, difenoconazole, hexaconazole, prothioconazole, propiconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, mancozeb, chlorothalonil, fluxapyroxade, benzovindiflupyr, isoflucipram and methyltetraprole, wherein the weight ratio of component (A) to component (B) is from 10:1 to 1:10 (or even more preferably from 7.5:1 to 1:7.5).

In another preferred composition according to the present invention, component (A) is compound No. X.04, methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxyprop-2-enoate, or a salt or tautomer thereof, and component (B) is a compound selected from the group consisting of cyproconazole, difenoconazole, hexaconazole, prothioconazole, propiconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, mancozeb, chlorothalonil, fluxapyroxade, benzovindiflupyr, isoflucipram and methyltetraprole, wherein the weight ratio of component (A) to component (B) is from 10:1 to 1:10 (or even more preferably from 7.5:1 to 1:7.5).

In a preferred composition according to the present invention, component (A) is compound No. X.01, methyl (Z)-2-(5-cyclobutyl-2-methylphenoxy)-3-methoxyprop-2-enoate, or a salt or tautomer thereof, and component (B) is a compound selected from the group consisting of cyproconazole, difenoconazole, prothioconazole, azoxystrobin, trifloxystrobin, pyraclostrobin and methyltetraprole, wherein the weight ratio of component (A) to component (B) is from 10:1 to 1:10 (or even more preferably from 7.5:1 to 1:7.5).

In another preferred composition according to the present invention, component (A) is compound No. X.02, methyl (Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxyprop-2-enoate, or a salt or tautomer thereof, and component (B) is a compound selected from the group consisting of cyproconazole, difenoconazole, prothioconazole, azoxystrobin, trifloxystrobin, pyraclostrobin and methyltetraprole, wherein the weight ratio of component (A) to component (B) is from 10:1 to 1:10 (or even more preferably from 7.5:1 to 1:7.5).

In another preferred composition according to the present invention, component (A) is compound No. X.03, methyl (Z)-2-(5-cyclopropyl-2-methylphenoxy)-3-methoxyprop-2-enoate, or a salt or tautomer thereof, and component (B) is a compound selected from the group consisting of cyproconazole, difenoconazole, prothioconazole, azoxystrobin, trifloxystrobin, pyraclostrobin and methyltetraprole, wherein the weight ratio of component (A) to component (B) is from 10:1 to 1:10 (or even more preferably from 7.5:1 to 1:7.5).

In another preferred composition according to the present invention, component (A) is compound No. X.04, methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxyprop-2-enoate, or a salt or tautomer thereof, and component (B) is a compound selected from the group consisting of cyproconazole, difenoconazole, prothioconazole, azoxystrobin, trifloxystrobin, pyraclostrobin and methyltetraprole, wherein the weight ratio of component (A) to component (B) is from 10:1 to 1:10 (or even more preferably from 7.5:1 to 1:7.5).

In one embodiment of the present invention, there is provided a synergistic fungicidal composition comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is

methyl (Z)-2-(5-cyclobutyl-2-methylphenoxy)-3-methoxyprop-2-enoate (compound X.01),

methyl (Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxyprop-2-enoate (compound X.02),

methyl (Z)-2-(5-cyclopropyl-2-methylphenoxy)-3-methoxyprop-2-enoate (compound X.03) or

methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxyprop-2-enoate (compound X.04)

or its agronomically acceptable salt,

And

component (B) is a compound selected from the group consisting of cyproconazole, difenoconazole, prothioconazole, azoxystrobin, trifloxystrobin, pyraclostrobin and methyltetraprole.

Preferably, in one embodiment of the present invention, there is provided a synergistic fungicidal composition comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is

methyl (Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxyprop-2-enoate

(connection X.02) or

methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxyprop-2-enoate (compound X.04);

or its agronomically acceptable salt,

And

component (B) is a compound selected from the group consisting of cyproconazole, difenoconazole, prothioconazole, azoxystrobin, trifloxystrobin, pyraclostrobin and methyltetraprole, wherein the weight ratio of component (A) to component (B) is from 10:1 to 1:10 (or even more preferably from 7.5:1 to 1:7.5).

More preferably, in one embodiment of the present invention, there is provided a synergistic fungicidal composition comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is

methyl (Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxyprop-2-enoate (compound X.02) or

methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxyprop-2-enoate (compound X.04)

or its agronomically acceptable salt,

And

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

Even more preferably, in one embodiment of the present invention, there is provided a synergistic fungicidal composition comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is

methyl (Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxyprop-2-enoate (compound X.02) or

methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxyprop-2-enoate (compound X.04)

or its agronomically acceptable salt,

And

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 from 7.5:1 to 1:7.5).

In another preferred embodiment of the present invention, there is provided a synergistic fungicidal composition comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is

methyl (Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxyprop-2-enoate (compound X.02) or

methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxyprop-2-enoate (compound X.04)

or its agronomically acceptable salt,

And

component (B) is a compound selected from the group consisting of cyproconazole, difenoconazole, hexaconazole, prothioconazole, propiconazole, fenpropidin, fenpropimorph, fludioxonil, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, mancozeb, folpet, chlorothalonil, fluxapyroxade, benzovindiflupyr, isoflucipram, pydiflumetofen, mefentrifluconazole, florylpicoxamide, methyltetraprole, 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-propanoyloxypyridine-2-carbonyl)amino]propanoate (preferably wherein the weight ratio of component (A) to component (B) is from 100:1 to 1:100).

Preferably, in this embodiment of the present invention, there is provided a synergistic fungicidal composition comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is

methyl (Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxyprop-2-enoate (compound X.02) or

methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxyprop-2-enoate (compound X.04)

or its agronomically acceptable salt, and

component (B) is a compound selected from the group consisting of cyproconazole, difenoconazole, prothioconazole, fenpropidin, fenpropimorph, fludioxonil, azoxystrobin, trifloxystrobin, pyraclostrobin, mancozeb, folpet, chlorothalonil, benzovindiflupyr, pydiflumetofen, mefentrifluconazole, florylpicoxamide, methyltetraprole, 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-propanoyloxypyridine-2-carbonyl)amino]propanoate, where 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)

The term "fungicide" as used herein means a compound that provides control, modification or prevention of fungal growth. The term "fungicidally effective amount" means the amount of such a compound or combination of such compounds that is capable of producing an effect on fungal growth. Controlling or modifying effects include all deviations from natural development such as killing, inhibition of development, etc., and prevention includes a barrier or other protective formation in or on a plant to prevent fungal infection.

The term "plants" refers to all physical parts of a plant, including seeds, sprouts, seedlings, roots, tubers, stems, petioles, leaves, and fruits.

The term "plant propagation material" means all generative parts of a plant, such as seeds, or vegetative parts of plants, such as cuttings and tubers. It includes seeds in the narrow sense, as well as roots, fruits, tubers, bulbs, rhizomes, and plant parts.

The term "growing place" as used herein means the fields in or on which plants are grown or where the seeds of cultivated plants are sown or where the seeds will be placed in the soil. It includes the soil, the seeds and seedlings, as well as the vegetation already grown.

Throughout this document, the expression "composition" means various mixtures or combinations of components (A) and (B) (including the embodiments defined above), for example in the separate form of a "ready mix", in a combined spray mixture composed of separate formulations of individual components of the active ingredients, such as a "tank mix", and in the combined use of individual active ingredients in the case of application in a sequential manner, i.e. one after the other over a sufficiently short period of time, such as several hours or days. The order of application of components (A) and (B) is not decisive for the implementation of the present invention.

The composition according to the present invention is effective against harmful microorganisms, such as microorganisms that cause phytopathogenic diseases, in particular against phytopathogenic fungi and bacteria.

The composition of the present invention can be used to control plant diseases caused by a wide range of fungal plant pathogens in the classes Basidiomycete, Ascomycete, Oomycete and/or Deuteromycete, Blasocladiomycete, Chrytidiomycete, Glomeromycete and/or Mucoromycete.

The composition is effective for controlling a wide range of plant diseases, such as those caused by pathogens that affect the leaves of ornamental, lawn, vegetable, field, grain and fruit crops.

Such pathogens may involve

Oomycetes, including Phytophthora diseases such as those caused by Phytophthora capsici, Phytophthora infestans, Phytophthora sojae, Phytophthora fragariae, Phytophthora nicotianae, Phytophthora cinnamomi, Phytophthora citricola, Phytophthora citrophthora and Phytophthora erythroseptica; Pythium diseases such as those caused by Pythium aphanidermatum, Pythium arrhenomanes, Pythium graminicola, Pythium irregulare and Pythium ultimum; diseases caused by Peronosporales such as Peronospora destructor, Peronospora parasitica, Plasmopara viticola, Plasmopara halstedii, Pseudoperonospora cubensis, Albugo Candida, Sclerophthora macrospora and Bremia lactucae; and others such as those caused by Aphanomyces cochlioides, Labyrinthula zosterae, Peronosclerospora sorghi and Sclerospora graminicola;

Ascomycetes, including diseases and/or rots presenting as mottling, spotting, blight or blight, such as those caused by Pleosporales such as Stemphylium solani, Stagonospora tainanensis, Spilocaea oleaginea, Setosphaeria turcica, Pyrenochaeta lycoperisici, Pleospora herbarum, Phoma destructiva, Phaeosphaeria herpotrichoides, Phaeocryptocus gaeumannii, Ophiosphaerella graminicola, Ophiobolus graminis, Leptosphaeria maculans, Hendersonia creberrima, Helminthosporium triticirepentis, Setosphaeria turcica, Drechslera glycines, Didymella bryoniae, Cycloconium oleagineum, Corynespora cassiicola, Cochliobolus sativus, Bipolaris cactivora, Venturia inaequalis, Pyrenophora teres, Pyrenophora tritici-repentis, Alternaria alternata, Alternaria brassicicola, Alternaria solani and Alternaria tomatophila, Capnodiales such as Septoria tritici, Septoria nodorum, Septoria glycines, Cercospora arachidicola, Cercospora sojina, Cercospora zeae-maydis, Cercosporella capsellae and Cercosporella herpotrichoides, Cladosporium carpophilum, Cladosporium effusum, Passalora fulva, Cladosporium oxysporum, Dothistroma septosporum, Isariopsis clavispora, Mycosphaerella fljiensis, Mycosphaerella graminicola, Mycovellosiella koepkeii, Phaeoisariopsis bataticola, Pseudocercospora vitis, P seudocercosporella herpotrichoides, Ramularia beticola, Ramularia collo-cygni, Magnaporthales such as Gaeumannomyces graminis, Magnaporihe grisea, Pyricularia oryzae, Diaporthales such as Anisogramma anomala, Apiognomonia errabunda, Cytospora platani, Diaporihe phaseolorum, Discula destructiva, Gnomonia fructicola, Greeneria uvicola, Melanconium juglandinum, Phomopsis viticola, Sirococcus clavigignenti-juglandacearum, Tubakia dryina, Dicarpella spp., Valsa ceratosperma, and others, such as Actinothyrium graminis, Ascochyta pisi, Aspergillus flavus, Aspergillus fumigatus, Aspergillus nidulans, Asperisporium caricae, Blumeriella jaapii, Candida spp., Capnodium ramosum, Cephaloascus spp., Cephalosporium gramineum, Ceratocystis paradoxa, Chaetomium spp., Hymenoscyphus pseudoalbidus, Coccidioides spp., Cylindrosporium padi, Diplocarpon malae, Drepanopeziza campestris, Elsinoe ampelina, Epicoccum nigrum, Epidermophyton spp., Eutypa lata, Geotrichum candidum, Gibellina cerealis, Gloeocercospora sorghi, Gloeodes pomigena, Gloeosporium perennans; Gloeotinia temulenta, Griphospaeria corticola, Kabatiella lini, Leptographium microsporum, Leptosphaerulinia crassiasca, Lophodermium seditiosum, Marssonina graminicola, Microdochium nivale, Monilinia fructicola, Monographella albescens, Monosporascus cannonballus, Naemacyclus spp., Ophiostoma novo-ulmi, Paracoccidioides brasiliensis, Penicillium expansum, Pestalotia rhododendri, Petriellidium spp., Pezicula spp., Phialophora gregata, Phyllachora pomigena, Phymatotrichum omnivora, Physalospora abdita, Plectosporium tabacinum, Polyscytalum pustulans, Pseudopeziza medicaginis, Pyrenopeziza brassicae, Ramulispora sorghi, Rhabdocline pseudotsugae, Rhynchosporium secalis, Sacrocladium oryzae, Scedosporium spp., Schizothyrium pomi, Sclerotinia sclerotiorum, Sclerotinia minor, Sclerotium spp., Typhula ishikariensis, Seimatosporium mariae, Lepteutypa cupressi, Septocyta ruborum, Sphaceloma perseae, Sporonema phacidioides, Stigmina palmivora, Tapesia yallundae, Taphrina bullata, Thielviopsis basicola, Trichoseptoria fructigena, Zygophiala jamaicensis; powdery mildew diseases such as those caused by Erysiphales such as Blumeria graminis, Erysiphe polygoni, Uncinula necator, Sphaerotheca fuligena, Podosphaera leucotricha, Podospaera macularis Golovinomyces cichoracearum, Leveillula taurica, Microsphaera diffusa, Oidiopsis gossypii, Phyllactinia guttata and Oidium arachidis; those caused by Botryosphaeriales such as Dothiorella aromatica, Diplodia seriata, Guignardia bidwellii, Botrytis cinerea, Botryotinia allii, Botryotinia fabae, Fusicoccum amygdali, Lasiodiplodia theobromae, Macrophoma theicola, Macrophomina phaseolina, Phyllosticta cucurbitacearum; anthracnose species such as Glommerelales such as Colletotrichum gloeosporioides, Colletotrichum lagenarium, Colletotrichum gossypii, Glomerella cingulata, and Colletotrichum graminicola; and wilt or late blight species, for example those caused by Hypocreales such as Acremonium strictum, Claviceps purpurea, Fusarium culmorum, Fusarium graminearum, Fusarium virguliforme, Fusarium oxysporum, Fusarium subglutinans, Fusarium oxysporum f.sp.cubense, Gerlachia nivale, Gibberella fujikuroi, Gibberella zeae, Gliocladium spp., Myrothecium verrucaria, Nectria ramulariae, Trichoderma viride, Trichothecium roseum, and Verticillium theobromae;

Basidiomycetes, including smut species such as those caused by Ustilaginales such as Ustilaginoidea virens, Ustilago nuda, Ustilago tritici, Ustilago zeae, rust species such as those caused by Pucciniales such as Cerotelium fwi, Chrysomyxa arctostaphyli, Coleosporium ipomoeae, Hemileia vastatrix, Puccinia arachidis, Puccinia cacabata, Puccinia graminis, Puccinia recondita, Puccinia sorghi, Puccinia hordei, Puccinia striiformis f.sp. Hordei, Puccinia striiformis f.sp. Secalis, Pucciniastrum coryli, or Uredinales, 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 spp., Exobasidium vexans, Marasmiellus inoderma, Mycena spp., Sphacelotheca reiliana, Typhula i shikari en sis, Urocystis agropyri, Itersonilia perplexans, Corticium invisum, Laetisaria fuciformis, Waitea circinata, Rhizoctonia solani, Thanetephorus cucurmeris, Entyloma dahliae, Entylomella microspora, Neovossia moliniae and Tilletia caries;

Blastocladiomycetes such as Physoderma maydis;

Mucoromycetes such as Choanephora cucurbitarum.; Mucor spp.; Rhizopus arrhizus; and diseases caused by other species and genera that are closely related to those listed above.

In addition to their fungicidal activity, the compositions may also have activity against bacteria such as Erwinia amylovora, Erwinia caratovora, Xanthomonas campestris, Pseudomonas syringae, Strptomyces scabies and other related species, as well as certain protozoa.

The composition according to the present invention is in particular effective against phytopathogenic fungi belonging to the following classes: ascomycetes (e.g. Venturia, Podosphaera, Erysiphe, Monilinia, Mycosphaerella, Uncinula); basidiomycetes (e.g. the genus Hemileia, Rhizoctonia, Phakopsora, Puccinia, Ustilago, Tilletia); fungi imperfecti (also known as deuteromycetes; e.g. Botrytis, Helminthosporium, Rhynchosporium, Fusarium, Septoria, Cercospora, Alternaria, Pyricularia and Pseudocercosporella); oomycetes (e.g. Phytophthora, Peronospora, Pseudoperonospora, Albugo, Bremia, Pythium, Pseudosclerospora, Plasmopara).

Agricultural crops of useful plants, in relation to which the composition according to the present invention can be applied, provide perennial and annual agricultural crops, such as berry plants, for example, varieties of blackberry, blueberry, cranberry, raspberry and strawberry; cereals, for example, barley, maize (corn), millet, oats, rice, rye, sorghum, triticale and wheat; fiber plants, for example, cotton, flax, hemp, jute and sisal; field agricultural crops, for example, sugar and fodder beet, coffee, hop varieties, mustard, oilseed rape (canola), poppy, sugar cane, sunflower, tea bush and tobacco; fruit trees, for example, apple, apricot, avocado, banana tree, cherry, citrus, nectarine, peach, pear and plum; Herbaceous plants such as Bermuda grass, bluegrass, bent grass, Eremochloa serpentina, fescue, ryegrass, St. Augustine's grass and zoysia japonica; Herbs such as basil, borage, chives, coriander, lavender, lovage, mint, oregano, parsley, rosemary, sage and thyme; Legumes such as beans, lentils, peas and soybeans; Nuts such as almonds, cashews, peanuts, hazelnuts, peanuts, pecans, pistachios and walnuts; Palms such as oil palm; Ornamental plants such as flowers, shrubs and trees; Other trees such as the cocoa tree, coconut palm, olive tree and rubber tree; vegetable crops such as asparagus, eggplant, broccoli, cabbage, carrot, cucumber, garlic, lettuce, squash, melon, okra, onion, pepper, potato, pumpkin, rhubarb, spinach and tomato, and woody vines such as grapes.

It should be understood that agricultural crops also include those agricultural crops that occur in nature, are obtained by conventional breeding methods or are obtained by genetic engineering. They include agricultural crops that are characterized by so-called introduced traits (e.g. improved shelf life, higher nutritional value and improved flavor and aroma qualities).

Crops also include those crops that have been made tolerant to herbicides such as bromoxynil or to classes of herbicides such as ALS inhibitors, EPSPS, GS, HPPD and PPO. An example of a crop that has been made tolerant to imidazolinones such as imazamox by conventional breeding methods is Clearfield® spring canola. Examples of crops that have been genetically engineered to be tolerant to herbicides include, for example, glyphosate- and glufosinate-resistant maize varieties commercially available under the trade names RoundupReady®, Herculex I® and LibertyLink®.

Agricultural crops are also to be understood as crops that are inherently resistant or that have been rendered resistant to harmful insects. They include plants transformed using recombinant DNA technologies, for example, in such a way that they are capable of synthesizing one or more toxins of selective action, such as those known, for example, from toxin-producing bacteria. Examples of toxins that can be expressed include 5-endotoxins, vegetative insecticidal proteins (Vip), insecticidal proteins of bacteria colonizing nematodes, and toxins produced by scorpions, arachnids, wasps and fungi.

An example of a crop that has been modified to express a Bacillus thuringiensis toxin is Bt maize KnockOut® (Syngenta Seeds). An example of a crop that contains more than one gene that confers insect resistance and thus expresses more than one toxin is VipCot® (Syngenta Seeds). Crops or their seed material can also be resistant to several types of pests (so-called stacked gene transgenic events if obtained by genetic modification). For example, a plant can be characterized by the ability to express an insecticidal protein while being tolerant to herbicides, such as Herculex I® (Dow AgroSciences, Pioneer Hi-Bred International).

The compounds of formula (I) (including any of the compounds X.01 to X.04) or fungicidal compositions according to the present invention containing a compound of formula (I) can be used to control or prevent phytopathogenic diseases, especially those caused by phytopathogenic fungi (such as Phakopsora pachyrhizi) on soybean plants.

In particular, transgenic soybean plants expressing toxins, such as insecticidal proteins, such as delta-endotoxins, such as CrylAc (CrylAc Bt protein). Accordingly, they may include transgenic soybean plants comprising the transgenic event MON87701 (see U.S. Patent No. 8,049,071 and related applications and patents, as well as WO 2014/170327 A1 (e.g., see the reference to Intacta RR ² PRO™ soybean in paragraph [008])), the transgenic event MON87751 (U.S. Patent Application Publication No. 2014/0373191), or the transgenic event DAS-81419 (U.S. Patent No. 8,632,978 and related applications and patents).

Other transgenic soybean plants may comprise the HPPD tolerance event SYHT0H2 (U.S. Patent Application Publication No. 2014/0201860 and related applications and patents), the glyphosate tolerance event MON89788 (U.S. Patent Application Publication No. 7,632,985 and related applications and patents), the dicamba tolerance event MON87708 (U.S. Patent Application Publication No. US 2011/0067134 and related applications and patents), the glyphosate and ALS tolerance event DP-356043-5 (U.S. Patent Application Publication No. US 2010/0184079 and related applications and patents), the glufosinate tolerance event A2704-12 (U.S. Patent Application Publication No. No. US 2008/0320616 and related applications and patents), transgenic event DP-305423-1 tolerance to ALS (US Patent Application Publication No. US 2008/0312082 and related applications and patents), transgenic event A5 547-127 - tolerance to glufosinate (US Patent Application Publication No. US 2008/0196127 and related applications and patents), transgenic event 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), transgenic event 127 tolerance to ALS (WO 2010/080829 and related applications and patents), transgenic event GTS 40-3-2 - tolerance to glyphosate, transgenic event DAS-68416-4 - tolerance to 2,4-dichlorophenoxyacetic acid and glufosinate, transgenic event FG72 tolerance to glyphosate and isoxaflutole, transgenic event BPS-CV127-9 tolerance to ALS and GU262 tolerance to glufosinate or transgenic event SYHT04R - tolerance to HPPD.

The compounds of formula (I) (including any of the compounds X.01 to X.04) or fungicidal compositions according to the present invention containing a compound of formula (I) can be used to control or prevent phytopathogenic diseases, especially those caused by phytopathogenic fungi (such as Phakopsora pachyrhizi) on soybean plants. In particular, certain elite varieties of soybean plants are known in the scientific literature in which R-gene packages conferring a degree of immunity or resistance to a particular Phakopsora pachyrhizi have been introgressed into the plant genome, see, for example, "Fighting Asian Soybean Rust", Langenbach C, et al, Front Plant Science 7(797) 2016).

An elite plant is any plant from an elite line, such that an elite plant is an illustrative plant of an elite variety. Non-limiting examples of elite soybean varieties that are commercially available to soybean farmers or 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, IA, USA); BPR0144RR, BPR 4077NRR, and BPR 4390NRR (Bio Plant Research, Camp Point, IL, USA); DKB17-51 and DKB37-51 (DeKalb Genetics, DeKalb, IL, USA); DP 4546 RR and DP 7870 RR (Delta & Pine Land Company, Lubbock, TX, USA); JG 03R501, JG 32R606C ADD, and JG 55R503C (JGL Inc., Greencastle, IN, USA); NKS 13-K2 (NK Division of Syngenta Seeds, Golden Valley, MN, USA); 90М01, 91М30, 92МЗЗ, 93М11, 94М30, 95М30, 97 В52, P008T22R2; P16T17R2; P22T69R; P25T51R; P34T07R2; P35T58R; P39T67R; P47T36R; P46T21R and P56T03R2 (Pioneer Hi-Bred International, Johnston, Iowa, USA); SG4771NRR and SG5161NRR/STS (Soygenetics, LLC, Lafayette, IN, USA); S00-K5, S11-L2, S28-Y2, S43-B1, S53-A1, S76-L9, S78-G6, S0009-M2; S007-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, KY, USA); Richer (Northstar Seed Ltd., Alberta, Canada); 14RD62 (Stine Seed Co., Iowa, USA) or Armor 4744 (Armor Seed, LLC, Arkansas, USA).

Thus, in a further preferred embodiment, fungicidal compositions according to the present invention comprising a compound of formula (I) (including any of the compounds X.01 to X.04) are used to provide control of Phakopsora pachyrhizi (including its fungicide-resistant strains, as indicated below) on elite soybean plant varieties in which R-gene packages conferring a degree of immunity or resistance to a particular Phakopsora pachyrhizi have been introgressed into the plant genome. Numerous benefits can be expected to result from the said use, such as improved biological activity, a preferred or broader spectrum of activity (including against susceptible and resistant strains of Phakopsora pachyrhizi), an improved safety profile, improved crop tolerance, synergistic interactions or potentiating properties, improved onset of action or longer residual activity, reduced number of applications and/or reduced application rates of compounds and formulations required for effective control of the phytopathogen (Phakopsora pachyrhizi), thus ensuring preferred resistance management practices, reduced environmental impact and reduced operator exposure.

Under certain circumstances, the fungicidal compositions according to the present invention containing a compound of formula (I), when used to control or prevent phytopathogenic diseases, especially those caused by phytopathogenic fungi (such as Phakopsora pachyrhizi) on soybean plants (in particular any of the transgenic soybean plants described above), may exhibit a synergistic interaction between the active ingredients.

Fungicidal compositions according to the present invention, containing a compound of formula (I) (including any of the compounds X.01-X.04), can be used in providing control or prevention of phytopathogenic diseases, especially phytopathogenic fungi (in particular Phakopsora pachyrhizi) on soybean plants.

In addition, to date, no cross-resistance has been observed between fungicidal compositions according to the present invention containing a compound of formula (I) (including any of compounds X.01-X.04) and existing fungicidal solutions used to provide control of Phakopsora pachyrhizi.

Indeed, fungicide-resistant strains of Phakopsora pachyrhizi have been reported in the scientific literature, with strains resistant to one or more fungicides from at least each of the following fungicide modes of action: sterol demethylation inhibitors (DMIs), quinone-binding site outside inhibitors (Qol) and succinate dehydrogenase inhibitors (SDHIs). See, for example: "Sensitivity of Phakopsora pachyrhizi towards quinone-outside-inhibitors and demethylation-inhibitors, and corresponding resistance mechanisms." Schmitz HK et al, Pest Manag Sci (2014) 70: 378–388; "First detection of a SDH variant with reduced SDHI sensitivity in Phakopsora pachyrhizi" Simoes 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 Manag Sci (2016) 72: 1211-1215.

Thus, in a preferred embodiment, fungicidal compositions according to the present invention comprising a compound of formula (I) (including any of the compounds X.01 to X.04) are used to provide control of Phakopsora pachyrhizi that is resistant to one or more fungicides of any of the following MoA classes of fungicides: sterol demethylation inhibitors (DMIs), quinone-binding site external inhibitors (QoIs) and succinate dehydrogenase inhibitors (SDHIs).

Compounds containing component A according to the present invention, wherein R ¹ , R ² , R ³ and R ⁴ are as defined for formula (I), can be prepared as shown in the following schemes.

Compounds of formula (I) wherein R ¹ , R ² , R ³ and R ⁴ are as defined above may be prepared by conversion via cross coupling of compounds of formula (II) wherein R ¹ , R ² and R ³ are as defined for compounds of formula (I) and R ¹¹ is a halide or pseudohalide such as chlorine, bromine, iodine, -OSO ₂ CF ₃ or -OSO ₂ (CF ₂ ) ₃ CF ₃ , and compounds of formula (III) wherein R ⁴ is as defined for compounds of formula (I) and M is a metalloid moiety or pseudometalloid moiety (e.g. M includes but is not limited to MgCl, ZnCl or B(OH) ₂ ), optionally in the presence of a metal salt such as LiCl or ZnCl ₂ and a suitable metal based 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 temperatures ranging from 20°C to 150°C. 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 SL Buchwald (Springer publications) or "Metal-Catalyzed Cross-Coupling Reactions", edited by Armin de Meijere and Francois Diederich (WILEY-VCH publications). This is shown in Scheme 1.

Alternatively, compounds of formula (I) can be prepared by reacting compounds of formula (IV), wherein R ¹ , R ² and R ³ are as defined for compounds of formula (I) and R is partially unsaturated, optionally substituted C ₃ -C ₇ cycloalkenyl, via a reductive process such as hydrogenation using a hydrogen source in the presence of a catalytic complex such as palladium on carbon in an organic solvent such as methanol, tetrahydrofuran or ethyl acetate at temperatures from 0°C to 150°C. For relevant examples, see: ACS Medicinal Chemistry Letters, 2016, 7, 508-51. 'Handbook of Heterogeneous Catalytic Hydrogenation for Organic Synthesis' by Shigeo Nishimura (published by Wiley-VCH) or 'The Handbook of Homogeneous Hydrogenation' ed. Johannes de Vries and Cornelis Elsevier (published by Wiley-VCH). This is shown in Figure 2.

Compounds of formula (IV) wherein R ¹ , R ² and R ³ are as defined for compounds of formula (I) and R ¹² is a partially saturated and optionally substituted C ₃ -C ₇ cycloalkenyl, can be prepared by cross-coupling a compound of formula (II) wherein R ¹ 1 is a halide or pseudohalide such as chlorine, bromine, iodine, -OSO ₂ CF ₃ or -OSO ₂ (CF ₂ ) ₃ CF ₃ and compounds of formula (V) wherein M is a metalloid or pseudometalloid species (e.g. M includes but is not limited to B(OH) ₂ , BPin, SnBu ₃ ) or hydrogen using a suitable catalyst complex such as palladium (tetrakis-triphenylphosphine) in a solvent such as 1,4-dioxane, dimethylformamide or tetrahydrofuran at temperatures from 0°C to 150°C, and optionally in the presence of a base (e.g. potassium phosphate). 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 SL Buchwald (Springer publications) or "Metal-Catalyzed Cross-Coupling Reactions", edited by Armin de Meijere and Francois Diederich (WILEY-VCH publications). This is shown in Scheme 3.

Compounds of formula (II) wherein R ¹ , R ² and R ³ are as defined for compounds of formula (I) and R ¹¹ is a halide or pseudohalide such as chlorine, bromine, iodine, -OSO ₂ CF ₃ or -OSO ₂ (CF ₂ ) ₃ CF ₃ , can be prepared from compounds of formula (VI) wherein R ¹ , R ² and R ³ are as defined for compounds of formula (I), R ¹¹ is as defined above and R ¹³ is H or C ₁ -C ₄ alkyl, by treatment with a suitable base such as sodium methoxide and a formylating agent such as methyl formate, optionally in a suitable solvent (e.g. tetrahydrofuran) to give compounds of formula (VIa) wherein R ¹ , R ² and R ³ are as defined for compounds of formula (I), R ¹¹ is as defined above and R ¹⁴ is H or methyl, followed by methylation with using a reagent such as dimethyl sulfate, optionally in the presence of a base such as K ₂ CO ₃ . 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.

Compounds of formula (VI), wherein R ¹ , R ² and R ³ are as defined for compounds of formula (I), R ¹¹ is as defined above and R ¹³ is H or C ₁ -C ₄ alkyl, can be prepared from compounds of formula (VII) wherein R ¹ , R ² and R ³ are as defined for compounds of formula (I) and R ¹¹ is as defined above, by treatment with a base such as K ₂ CO ₃ and an alkylating agent of formula (VIII), wherein R ¹³ is H or C ₁ -C ₄ alkyl, in an organic solvent such as dimethylformamide or N-methylpyrrolidone. Compounds of formula (VII) are commercially available or are readily prepared from commercially available compounds by standard functional group transformations as described in March's Advanced Organic Chemistry, Smith and March, 6th edition, Wiley, 2007. This is shown in Scheme 5.

Compounds of formula (I) wherein R ¹ , R ² , R ³ and R ⁴ are as defined for compounds of formula (I) may also be prepared from compounds of formula (IX) wherein R ¹ , R ² , R ³ and R ⁴ are as defined for compounds of formula (I) and R ¹³ is H or C ₁ -C ₄ alkyl by treatment with a base such as sodium methoxide and a formylating agent such as methyl formate to give compounds of formula (X) wherein R ¹ , R ² , R ³ and R ⁴ are as defined for compounds of formula (I) and R ¹⁴ is H or methyl, followed by methylation with a reagent such as dimethyl sulfate in the presence of a base such as K ₂ CO ₃ . For relevant examples, see Journal of Agricultural and Food Chemistry, 2007, 55, 5697–5700, Molecules, 2010, 75, 9024–9034, and Organic Process Research and Development, 2015, 19, 639–645. This is shown in Scheme 6.

Compounds of formula (IX), wherein R ¹ , R ² and R ³ are as defined for compounds of formula (I) and R ⁴ is an optionally substituted cyclopropyl group, can be prepared from compounds of formula (XI), wherein R ¹ , R ² and R ³ are as defined for compounds of formula (I) and R ¹⁵ is an optionally substituted alkenyl group, 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. This is shown in Scheme 7.

Compounds of formula (XI), wherein R ¹ , R ² and R ³ are as defined for compounds of formula (I), R ¹⁵ is as defined above and R ¹³ is H or C ₁ -C ₄ alkyl, can be prepared from compounds of formula (XII), wherein R ¹ , R ² and R ³ are as defined for compounds of formula (I) and R ¹⁵ is as defined above, by treatment with a base such as K ₂ CO ₃ and an alkylating agent of formula (VIII), wherein R ¹³ is H or C ₁ -C ₄ alkyl, in an organic solvent such as dimethylformamide or N-methylpyrrolidone. This is shown in Scheme 8. For relevant examples, see European Journal of Organic Chemistry, 2015, 2197-2204. Compounds of formula (VIII) are commercially available or are readily prepared from commercially available compounds by standard functional group transformations as described in March's Advanced Organic Chemistry, Smith and March, 6th edition, Wiley, 2007.

Compounds of formula (XII), wherein R ¹ , R ² and R ³ are as defined for compounds of formula (I) and R ¹⁵ is as defined above, can be prepared by carrying out the transformation by coupling compounds of formula (VII), wherein R ¹ , R ² and R ³ are as defined for compounds of formula (I) and R ¹¹ is a halide or pseudohalide such as chlorine, bromine, iodine, -OSO ₂ CF ₃ or -OSO ₂ (CF ₂ ) ₃ CF ₃ , and compounds of formula (XIII), wherein R ¹⁵ is as defined above and M is a metalloid moiety or pseudometalloid moiety (e.g. M includes but is not limited to B(OH) ₂ , BPin, SnBu ₃ ) or hydrogen using a suitable catalyst complex such as palladium (tetrakis-triphenylphosphine) in a suitable solvent such as dioxane, dimethylformamide or tetrahydrofuran at values temperatures from 0°C to 150°C and optionally in the presence of a base such as potassium phosphate or potassium carbonate. For relevant examples, see Journal of Medicinal Chemistry, 2015, 58, 9258-9272 and Journal of Medicinal Chemistry, 2014, 57, 1252-1275. This is shown in Scheme 9.

The functional group transformations described in the preceding schemes are known to those skilled in the art. An extensive 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 in Comprehensive Organic Transformations: A Guide to Functional Group Preparations, edited by Richard C. Larock, Wiley-VCH, New York 1999.

If mixtures of isomers are obtained as a result of the synthesis, separation is usually not absolutely necessary, since in some cases individual isomers may interconvert during preparation for use or during use (e.g. under the influence of light, acids or bases). Such conversions may also occur after use, e.g. during plant treatment in the treated plant or in the harmful fungus to be controlled.

The compositions of the present invention, including all of the embodiments disclosed above and their preferred examples, can be mixed with one or more additional pesticides, including additional fungicides, insecticides, nematicides, bactericides, acaricides, growth regulators, chemosterilants, chemical signaling substances, repellents, attractants, pheromones, nutritional stimulants or other biologically active compounds to form a multi-component pesticide that provides an even broader spectrum of protection for agricultural crops.

Examples of such agricultural protective agents that can be formulated according to the present invention are fungicides such as etridiazole, fluazinam, benalaxyl, benalaxyl-M (kiralaxyl), furalaxyl, metalaxyl, metalaxyl-M (mefenoxam), dodicin, N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylformamidine, N'-[4-(4,5-dichlorothiazol-2-yloxy)-2,5-dimethylphenyl]-N-ethyl-N-methylformamidine, N'-[4-[[3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl]oxy]-2,5-dimethylphenyl]-N-ethyl-N-methylformamidine, ethirimol, 3'-chloro-2-methoxy-N-[(3RS)-tetrahydro-2-oxofuran-3-yl]acetyl-2',6'-xylidide (clozilacon), cyprodinil, mepanipyrim, pyrimethanil, dithianon, aureofungin, blasticidin-S, biphenyl, chloroneb, dicloran, benzovindiflupyr, pydiflumetofen, hexachlorobenzene, quintozene, teknazen (TCNB), tolkofos-methyl, metrafenone, 2,6-dichloro-N-(4-trifluoromethylbenzyl)benzamide, fluopicolide (flupocolide), thioximide, flusulfamide, benomyl, carbendazim, carbendazim hydrochloride, chlorphenazole, fuberidazole, thiabendazole, thiophanate-methyl, benthiavalicarb, chlobenthiazone, probenazole, acibenzolar, betoxazine, pyriophenone (IKF-309), acibenzolar-v-methyl, pyribencarb (KIF-7767), butylamine, 3-iodo-2-propynyl-n-butylcarbamate (IPBC), iodocarb (isopropanylbutylcarbamate), isopropanylbutylcarbamate (iodocarb), picarbutrazox, polycarbamate, propamocarb, tolprocarb, 3-(difluoromethyl)-N-(7-fluoro-1,1,3,3-tetramethylindan-4-yl)-1-methylpyrazol-4-carboxamide diclocymet, N-[(5-chloro-2-isopropylphenyl)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, carpropamide, chlorothalonil, flumorph, copper oxinate, cymoxanil, phenamacryl, cyazofamide, flutianil, thithiophene, chlozolinate, iprodione, procymidone, vinclozolin, bupirimate, dinoctone, dinopentone, dinobuton, dinocap, meptyldinocap, diphenylamine, phosdifene, 2,6-Dimethyl-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetraone, azitiram, etem, ferbam, mancozeb, maneb, metam, metiram (Polyram), metiram-zinc, nabam, propineb, thiram, vapam (metam sodium), zineb, ziram, dithioether, isoprothiolane, ethaboxam, fosetyl, fosetyl-Al (fosetyl-Al), methyl bromide, methyl iodide, methyl isothiocyanate, cyclafuramid, fenfuram, validamycin, streptomycin, (2RS)-2-bromo-2-(bromomethyl)glutaronitrile (bromothalonil), dodine, doguadine, guazatine, iminoctadine, iminoctadine triacetate, 2,4-D, 2,4-DB, kasugamycin, dimethirimol, fenhexamide, hymexazole, hydroxyisoxazole, imazalil, imazalyl sulfate, oxpoconazole, pefurazoate, prochloraz, triflumizole, fenamidone, Bordeaux mixture, calcium polysulfide, copper acetate, copper carbonate, copper hydroxide, copper naphthenate, copper oleate, copper oxychloride, copper oxyquinolate, copper silicate, copper sulfate, copper tallate, copper oxide, sulfur, carbaryl, phthalide (phthalide), ding junezuo (Jun Si Qi), oxathiapiproline, fluorimide, mandipropamide, KSF-1002, benzamorph, dimethomorph, fenpropimorph, tridemorph, dodemorph, diethofencarb, fentin acetate, fentin hydroxide, carboxin, oxycarboxin, drazoxolone, famoxadone, meta-phenylphenol, para-phenylphenol, tribromophenol (TBP), 2-[2-[(7,8-difluoro-2-methyl-3-quinolyl)oxy]-6-fluorophenyl]propan-2-ol, 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phenyl]propan-2-ol, cyflufenamide, ofurace, oxadixyl, flutolanil, mepronil, isofetamide, fenpiclonil, fludioxonil, pencycuron, edifenphos, iprobenfos, pyrazophos, phosphoric acids, tecloftalam, captafol, captan, dithalymphos, triforine, fenpropidin, piperalin, osthole, 1-methylcyclopropene, 4-CPA, chlormequat, clofencet, dichlorprop, dimethipine, endothal, ethephon, flumetralin, forchlorfenuron, gibberellic acid, gibberellins, hymexazole, maleic hydrazide, mepiquat, naphthaleneacetamide, paclobutrazol, prohexadione, prohexadione calcium, thidiazuron, tribufos (tributylphosphorothritioate), trinexapac, uniconazole, α-naphthaleneacetic acid, polyoxin D (polyoxrim), BLAD, chitosan, fenoxanil, folpet, 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichlorophenyl)ethyl]pyrazole-4-carboxamide, bixafen, fluxapyroxad, furametpyr, isopyrazam, penflufen, penthiopyrad, sedaxan, fenpyrazamine, diclomezine, pyrifenox, boscalid, fluopyram, diflumetorim, fenarimol, 5-fluoro-2-(p-tolylmethoxy)pyrimidin-4-amine, ferimzone, dimethachlone (dimethachlone), pyroquilone, proquinazid, ethoxyquin, quinoxyfen, 4,4,5-trifluoro-3,3-dimethyl-1-(3-quinolyl)isoquinoline, 4,4-difluoro-3,3-dimethyl-1-(3-quinolyl)isoquinoline, 5-fluoro-3,3,4,4-tetramethyl-1-(3-quinolyl)isoquinoline, 9-fluoro-2,2-dimethyl-5-(3-quinolyl)-3H-1,4-benzoxazepine, tebufloquine, oxolinic acid, quinomethionate (oxythioquinox, quinoxymethionate), spiroxamine, (E)-N-methyl-2-[2-(2,5-dimethylphenoxymethyl)phenyl]-2-methoxyiminoacetamide, (mandestrobin), azoxystrobin, kumoxystrobin, dimoxystrobin, enestroburin, enoxastrobin, fenamistrobin, flufenoxystrobin, fluoxastrobin, kresoxim-methyl, mandestrobin, metaminostrobin, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, triclopyricarb, trifloxystrobin, amisulbrom, dichlofluanid, tolylfluanid, but-3-ynyl-N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenylmethylene]amino]oxymethyl]-2-pyridyl]carbamate, dazomet, isothianil, tiadinil, thifluzamide, benthiazole (TCMTV), silthiofam, zoxamide, anilazine, tricyclazole, (+-)-cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol (huanjunzuo), 1-(5-bromo-2-pyridyl)-2-(2,4-difluorophenyl)-1,1-difluoro-3-(1,2,4-triazol-1-yl)propan-2-ol, 2-(1-tert-butyl)-1-(2-chlorophenyl)-3-(1,2,4-triazol-1-yl)-propan-2-ol (TCDP), azaconazole, bitertanol (biloxazole), bromuconazole, climbazole, cyproconazole, difenoconazole, dimethconazole, diniconazole, diniconazole-M, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, ipfentrifluconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triazoxide, triticonazole, mefentrifluconazole, 2-[[(1R,5S)-5-[(4-fluorophenyl)methyl]-1-hydroxy-2,2-dimethylcyclopentyl]methyl]-4H-1,2,4-triazol-3-thione, 2-[[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl]-4H-1,2,4-triazol-3-thione, amethoctradine (imidium), iprovalicarb, valifenalate, 2-benzyl-4-chlorophenol (chlorophen), allyl alcohol, azaphenidine, benzalkonium chloride, chloropicrin, cresol, daracid, dichlorophene (dichlorophen), difenzoquat, dipyrithione, N-(2-p-chlorobenzoylethyl)hexaminium chloride, NNF-0721, octhilinone, oxasulfuron, propamidine, and propionic acid,

insecticides such as abamectin, acephate, acetamiprid, amidoflumet (S-1955), avermectin, azadirachtin, azinphos-methyl, bifenthrin, bifenazate, buprofezin, carbofuran, cartap, chlorantraniliprole (DPX-E2Y45), chlorfenapyr, chlorfluazuron, chlorpyrifos, chlorpyrifos-methyl, cromafenozide, clothianidin, cyflumetofen, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, cypermethrin, cyromazine, deltamethrin, diafenthiuron, diazinon, dieldrin, diflubenzuron, dimefluthrin, dimethoate, dinotefuran, diofenolan, Emamectin, Endosulfan, Esfenvalerate, Etiprole, Fenothiocarb, Fenoxycarb, Fenpropathrin, Fenvalerate, Fipronil, Flonicamid, Flubendiamide, Flucythrinate, Tau-Fluvalinate, Flufenerim (UR-50701), Flufenoxuron, Fonofos, Halofenozide, Hexaflumuron, Hydramethylnon, Imidacloprid, Indoxacarb, Isofenphos, Lufenuron, Malathion, Metaflumizone, Metaldehyde, Methamidophos, Methidathion, Methomyl, Methoprene, Methoxychlor, Metofluthrin, Monocrotophos, Methoxyfenozide, Nitenpyram, Nithiazine, Novaluron, Noviflumuron (XDE-007), Oxamyl, Parathion, Parathion-methyl, Permethrin, phorate, fosalone, phosmet, phosphamidon, pirimicarb, profenofos, profluthrin, pymetrozine, pyrafluprole, pyrethrin, pyridalyl, pyrifluquinazone, pyriprole, pyriproxyfen, rotenone, ryanodine, spinetoram, spinosad, spirodiclofen, spiromesifen (BSN 2060), spirotetramate, sulprofos, tebufenozide, teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos, thiacloprid, thiamethoxam, thiodicarb, thiosultap sodium, tralomethrine, triazamate, trichlorfon and triflumuron;

bactericides such as streptomycin;

acaricides such as amitraz, quinomethionate, chlorobenzilate, cyenopyrafen, cyhexatin, dicofol, dienochlor, etoxazole, fenazaquin, fenbutatin oxide, fenpropathrin, fenpyroximate, hexythiazox, propargite, pyridaben and tebufenpyrad; and biological agents such as Bacillus thuringiensis, Bacillus thuringiensis delta-endotoxin, baculovirus and entomopathogenic bacteria, viruses and fungi.

Other examples of "illustrative" mixture-based compositions include the following (wherein the term "TX" is a compound (as defined in component (A) of the compositions of the present invention) selected from compound No. X.01, X.02, X.03 or X.04 as defined in Table X above): a compound selected from the group of substances consisting of petroleum oils + TX, 1,1-bis(4-chlorophenyl)-2-ethoxyethanol + TX, 2,4-dichlorophenylbenzenesulfonate + TX, 2-fluoro-N-methyl-N-1-naphthylacetamide + TX, 4-chlorophenylphenylsulfone + TX, acetoprol + TX, aldoxycarb + TX, amidithione + TX, amidothioate + TX, amiton + TX, amiton hydroxalate + TX, amitraz + TX, aramite + TX, arsenic oxide + TX, azobenzene + TX, azotoate + TX, benomyl + TX, benoxaphos + TX, benzyl benzoate + TX, bixaphen + TX, brofenvalerate + TX, broflanilide + TX, bromocyclene + TX, bromophos + TX, bromopropylate + TX, buprofezin + TX, butocarboxim + TX, butoxycarboxim + TX, butylpyridabene + TX, calcium polysulfide + TX, camphechlor + TX, carbanolate + TX, carbophenothione + TX, cimiazole + TX, quinomethionate + TX, chlorobenzide + TX, chlordimeform + TX, hydrochloride chlordimeform + TX, chlorphenetol + TX, chlorphenson + TX, chlorphensulfide + TX, chlorobenzilate + TX, chloromebuform + TX, chloromethiuron + TX, chloropropylate + TX, chlorothiophos + TX, cinerin I + TX, cinerin II + TX, cinerin + TX, closantel + TX, coumaphos + TX, crotamiton + TX, crotoxiphos + TX, kufraneba + TX, cyanoate + TX, DCPM + TX, DDT + TX, demefion + TX, demefion-O + TX, demefion-S + TX, demeton-methyl + TX, demeton-O + TX, demeton-O-methyl + TX, demeton-S + TX, demeton-S-methyl + TX, demeton-S-methylsulfone + TX, dichlorofluanide + TX, dichlorvos + TX, diclifos + TX, dienochlor + TX, dimefox + TX, dinex + TX, dinex-diclexin + TX, dinocapa-4 + TX, dinocapa-6 + TX, dinoctone + TX, dinopentone + TX, dinosulfone + TX, dinoterbone + TX, dioxathion + TX, diphenylsulfone + TX, disulfiram + TX, DNOC + TX, dofenapine + TX, doramectin + TX, endothione + TX, eprinomectin + TX, methyl ethoate + TX, etrimphos + TX, phenazaflor + TX, phenbutatin oxide + TX, phenothiocarb + TX, fenpyrade + TX, fenpiroximate + TX, fenpyrazamine + TX, fenzone + TX, fentrifanil + TX, flubenzymine + TX, flucycloxuron + TX, fluenethyl + TX, fluorbenzide + TX, FMC 1137 + TX, formetanate + TX, hydrochloride formethanate + TX, formparanate + TX, gamma-NSN + TX, gliodine + TX, galfenprox + TX, hexadecylcyclopropanecarboxylate + TX, isocarbophos + TX, jasmoline I + TX, jasmoline II + TX, iodofenphos + TX, lindane + TX, malonobene + TX, mecarbam + TX, mephospholane + TX, mesulfen + TX, metacryphos + TX, methyl bromide + TX, metolcarb + TX, mexacarbate + TX, milbemycin oxime + TX, mipafox + TX, monocrotophos + TX, morphothione + TX, moxidectin + TX, naled + TX, 4-chloro-2-(2-chloro-2-methylpropyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazin-3-one + TX, nifluridide + TX, nikkomycin + TX, nitrilecarb + TX, complex of nitrilecarb and zinc chloride 1:1 + TX, omethoate + TX, oxideprophos + TX, oxydisulfoton + TX, pp'-DDT + TX, parathion + TX, permethrin + TX, phencapton + TX, fozalone + TX, phospholan + TX, phosphamidone + TX, polychloroterpenes + TX, polynactins + TX, proclonol + TX, promacyl + TX, propoxur + TX, protidation + TX, protoate + TX, pyrethrin I + TX, pyrethrin II + TX, pyrethrins + TX, pyridafention + TX, pyrimitate + TX, quinalphos + TX, quinthiophos + TX, R-1492 + TX, fosglycine + TX, rotenone + TX, shradan + TX, sebuphos + TX, selamectin + TX, sophamide + TX, SSI-121 + TX, sulfiram + TX, sulfluramide + TX, sulfotepa + TX, sulfur + TX, diflovidazine + TX, tau-fluvalinate + TX, TERB + TX, terbam + TX, tetradiphon + TX, tetrasula + TX, thiaphenox + TX, thiocarboxyme + TX, thiophanox + TX, thiometon + TX, thioquinox + TX, thuringiensin + TX, triamiphos + TX, triarathene + TX, triazophos + TX, triazuron + TX, triphenofos + TX, trinactin + TX, vamidothione + TX, vaniliprole + TX, betoxazin + TX, copper dioctanoate + TX, copper sulfate + TX, cibutrin + TX, dichloron + TX, dichlorophen + TX, endothal + TX, fentin + TH, slaked lime + TH, nabam + TH, quinoclamine + TH, quinonamide + TH, simazine + TH, triphenyltin acetate + TH, triphenyltin hydroxide + TH, crufomate + TH, piperazine + TH, thiophanate + TH, chloralose + TH, fenthion + TH, pyridin-4-amine + TH, strychnine + TH, 1-hydroxy-1H-pyridine-2-thione + TH, 4-(quinoxalin-2-ylamino)benzenesulfonamide + TH, 8-hydroxyquinoline sulfate + TH, bronopol + TH, copper hydroxide + TH, cresol + TH, dipyrithione + TH, dodicin + TH, fenaminosulf + TH, formaldehyde + TH, hydrahaphene + TX, kasugamycin + TX, kasugamycin hydrochloride hydrate + TX, nickel bis(dimethyldithiocarbamate) + TX, nitrapyrine + TX, octhilinone + TX, oxolinic acid + TX, oxytetracycline + TX, potassium hydroxyquinoline sulfate + TX, probenazole + TX, streptomycin + TX, streptomycin sesquisulfate + TX, tecloftalam + TX, thiomersal + TX, Adoxophyes orana GV + TX, Agrobacterium radiobacter + TX, Amblyseius spp. + TX, Anagrapha falcifera NPV + TX, Anagrus atomus + TX, Aphelinus abdominalis + TX, Aphidius colemani + TX, Aphidoletes aphidimyza + TX, Autographa californica NPV + TX, Bacillus sphaericus Neide + TX, Beauveria brongniartii + TX, Chrysoperla camea + TX, Cryptolaemus montrouzieri + TX, Cydia pomonella GV + TX, Dacnusa sibirica + TX, Diglyphus isaea + TX, Encarsia formosa + TX, Eretmocerus eremicus + TX, Heterorhabditis bacteriophora and H. megidis + TX, Hippodamia convergens + TX, Leptomastix dactylopii + TX, Macrolophus caliginosus + TX, Mamestra brassicae NPV + TX, Metaphycus helvolus + TX, Metarhizium anisopliae var. acridum + TX, Metarhizium anisopliae var. anisopliae + TX, Neodiprion sertifer NPV and N. lecontei NPV + TX, Orius spp. + TX, Paecilomyces fumosoroseus + TX, Phytoseiulus persimilis + TX, Steinemema bibionis + TX, Steinemema carpocapsae + TX, Steinemema feltiae + TX, Steinemema glaseri + TX, Steinemema riobrave + TX, Steinemema riobravis + TX, Steinemema scapterisci + TX, Steinemema spp. + TX, Trichogramma spp. + TX, Typhlodromus occidentalis + TX, Verticillium lecanii + TX, afolate + TX, bisazira + TX, busulfan + TX, dimatifa + TX, hemela + TX, hemp + TX, metepa + TX, methiothepa + TX, methylafolate + TX, morzide + TX, penfluron + TX, tepy + TX, thiochempy + TX, thiotepa + TX, tretamine + TX, uredepy + 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)-tetradeca-4,10-dien-1-ylacetate + 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)-eicos-13-en-10-one + TX, (Z)-tetradec-7-en-1-ala + TX, (Z)-tetradec-9-en-1-ol + TX, (Z)-tetradec-9-en-1-yl acetate + TX, (7E,9Z)-dodeca-7,9-diene-1-alacetate + TX, (9Z,11E)-tetradeca-9,11-dien-1-ylacetate + TX, (9Z,12E)-tetradeca-9,12-dien-1-ylacetate + TX, 14-methyloctadec-1-ene + TX, 4-methylnonan-5-ol and 4-methylnonan-5-one + TX, alpha-multistriatin + TC, brevicomina + TC, codlelur + TC, codelemona + TC, quelur + TC, disparlura + TC, dodec-8-en-1-yl acetate + TC, dodec-9-en-1-yl acetate + TX, dodec-8 + TC, 10-dien-1-yl acetate + TC, dodec-9-en-1-yl acetate + TC, ethyl 4-methyloctanoate + TC, eugenol + TC, frontalina + TX, grandlura + TX, grandlura I + TX, grandlura II + TX, grandlura III + TX, grandlura IV + TX, hexalura + TX, ipsdienol + TX, ipsenol + TX, japonilura + TX, lineatina + TX, litlura + TX, luplura + TX, medlura + TX, megatomoic acid + TX, methyleugenol + TX, muscalure + TX, octadeca-2,13-dien-1-ylacetate + TX, octadeca-3,13-dien-1-yl acetate + TX, orphralur + TX, oryctalur + TX, ostramon + TX, siglur + TX, sordidine + TX, sulcatol + TX, tetradec-11-en-1-ylacetate + TX, trimedlura + TX, trimedlura A + TX, trimedlura B ₁ + TX, trimedlura B ₂ + TX, trimedlura C + TX, tran-colla + TX, 2-(octylthio)-ethanol + TX, butopyronoxyl + TX, butoxy(polypropylene glycol) + TX, dibutyl adipate + TX, dibutyl phthalate + TX, dibutyl succinate + TX, diethyltoluamide + TX, dimethyl carbate + TX, dimethyl phthalate + TX, ethylhexanediol + TX, hexamide + TX, methquin-butyl + TX, methylneodecanamide + TX, oxamate + TX, picaridin + TX, 1-dichloro-1-nitroethane + TX, 1,1-dichloro-2,2-bis(4-ethylphenyl)ethane + TX, 1,2-dichloropropane with 1,3-dichloropropene + TX, 1-bromo-2-chloroethane + TX, 2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate + TX, 2,2-dichlorovinyl-2-ethylsulfinylethyl methyl phosphate + TX, 2-(1,3-dithiolan-2-yl)phenyl dimethylcarbamate + TX, 2-(2-butoxyethoxy)ethyl thiocyanate + TX, 2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methylcarbamate + TX, 2-(4-chloro-3,5-xylyloxy)ethanol + TX, 2-chlorovinyl diethyl phosphate + TX, 2-imidazolidone + TX, 2-isovalerylindane-1,3-dione + TX, 2-methyl(prop-2-ynyl)aminophenyl methylcarbamate + TX, 2-thiocyanatoethyl laurate + TX, 3-bromo-1-chloroprop-1-ene + TX, 3-methyl-1-phenylpyrazol-5-yldimethylcarbamate + TX, 4-methyl(prop-2-ynyl)amino-3,5-xylylmethylcarbamate + TX, 5,5-dimethyl-3-oxocyclohex-1-enyldimethylcarbamate + TX, acetone + TX, acrylonitrile + TX, aldrin + TX, allosamidine + TX, alloxycarb + TX, alpha-ecdysone + TX, aluminum phosphide + TX, aminocarb + TX, anabasine + TX, atidation + TX, azametifos + TX, delta-endotoxins Bacillus thuringiensis + TX, barium hexafluorosilicate + TX, barium polysulfide + TX, bartrin + TX, Bayer 22/190 + TX, Bayer 22408 + TX, beta-cyfluthrin + TX, beta-cypermethrin + TX, bioethanomethrin + TX, biopermethrin + TX, bis(2-chloroethyl) ether + TX, borax + TX, bromfenvinphos + TX, bromine-DDT + TX, bufencarb + TX, butacarb + TX, butathiophos + TX, butonate + TX, calcium arsenate + TX, calcium cyanide + TX, carbon disulfide + TC, carbon tetrachloride + TC, cartap hydrochloride + TC, cevadin + TC, chlorobicyclene + TC, chlordane + TC, chlordecone + TC, chloroform + TC, chloropicrin + TC, chlorphoxime + TC, chlorprazophos + TC, cis-resmethrin + TC, cismethrin + TC, clocitrin + TC, copper acetoarsenite + TC, copper arsenate + TX, copper oleate + TX, cumitoate + TX, cryolite + TX, CS 708 + TX, cyanophenphos + TX, cyanophos + TX, cycletrin + TX, cythioate + TX, d-tetramethrin + TX, DAEP + TX, dazomet + TX, decarbofuran + TX, diamidaphos + TX, dicaptone + TX, dichlorofenthione + TX, dicresyl + TX, dicyclanil + TX, dieldrin + TX, diethyl-5-methylpyrazol-3-ylphosphate + TX, dilor + TX, dimefluthrin + TX, dimethane + TX, dimetrin + TX, dimethylvinphos + TX, dimethylane + TX, dinoprop + TX, dinosama + TX, dinoseb + TX, diophenolan + TX, dioxabenzophos + TX, diticrophos + TX, DSP + TX, ecdysterone + TX, EI 1642 + TX, EMPC + TX, ERBP + TX, ethaphos + TX, etiophencarb + TX, ethyl formate + TX, ethylene dibromide + TX, ethylene dichloride + TX, ethylene oxide + TX, EXD + TX, fenchlorvos + TX, fenetacarb + TX, fenitrothion + TX, fenoxacrim + TX, fenpyritrin + TX, fensulfothione + TX, fenthion-ethyl + TX, flucofuron + TX, fosmethylane + TX, fospirate + TX, fostiethane + TX, furathiocarb + TX, furethrin + TX, guazatine + TX, guazatine acetates + TX, sodium tetrathiocarbonate + TX, galfenprox + TX, HCH + TX, HEOD + TX, heptachlor + TX, heterophos + TX, HHDN + TX, hydrogen cyanide + TX, hiquincarb + TX, IPSP + TX, isazophosa + TX, isobenzan + TH, isodrine + TH, isofenphos + TH, isolane + TH, isoprothiolane + TH, isoxathion + TH, juvenile hormone I + TH, juvenile hormone II + TH, juvenile hormone III + TH, kelevan + TH, kinoprene + TH, lead arsenate + TH, leptophos + TH, lirimphos + TH, lithidathion + TH, m-cumenyl methylcarbamate + TH, magnesium phosphide + TH, mazidox + TH, mecarfone + TH, menazon + TH, mercuric chloride + TH, mesulfenfos + TH, metam + TH, metam potassium + TH, metam sodium + TH, methanesulfonyl fluoride + TH, metocrophos + TC, methoprene + TC, methotrine + TC, methoxychlor + TC, methyl isothiocyanate + TC, methyl chloroform + TC, methylene chloride + TC, methoxadiazone + TC, mirex + TC, naphthalophos + TC, naphthalene + TC, NC-170 + TC, nicotine + TC, sulfate nicotine + TX, nithiazine + TX, nornicotine + TX, O-5-dichloro-4-iodophenyl-O-ethylethylphosphonothioate + TX, O,O-diethyl-O-4-methyl-2-oxo-2H-chromen-7-ylphosphorothioate + TX, O,O-diethyl-O-6-methyl-2-propylpyrimidin-4-ylphosphorothioate + TX, O,O,O',O'-tetrapropyldithiopyrophosphate + TX, oleic acid + TX, para-dichlorobenzene + TX, parathion-methyl + TX, pentachlorophenol + TX, pentachlorophenyl laurate + TX, pH 60-38 + TX, phencapton + TX, phosnichlor + TX, phosphine + TX, phoxim-methyl + TX, pyrimethafos + TX, isomers of polychlorodicyclopentadiene + TX, potassium arsenite + TX, potassium thiocyanate + TX, precocene I + TX, precocene II + TX, precocene III + TX, primidophos + TX, profluthrin + TX, promecarb + TX, prothiophos + TX, pyrazophos + TX, pyresmethrin + TX, quassia + TX, quinalphos-methyl + TX, quinothione + TX, rafoxanide + TX, resmethrin + TX, rotenone + TX, cadetrin + TX, ryanium + TX, ryanodine + TX, sabadilla + TX, shradana + TX, sebuphos + TX, SI-0009 + TX, tiapronil + TC, sodium arsenite + TC, sodium cyanide + TC, sodium fluoride + TC, sodium hexafluorosilicate + TC, sodium pentachlorophenoxide + TC, sodium selenate + TC, sodium thiocyanate + TC, sulcofuron + TC, sulcofuron-sodium + TC, sulfuryl fluoride + TC, sulprophos + TC, tar oils + TX, tazimkarba + TX, TDE + TX, tebupyrimphos + TX, temephos + TX, terallethrin + TX, tetrachloroethane + TX, ticrophos + TX, thiocyclam + TX, thiocyclam hydrooxalate + TX, thionazine + TX, thiosultap + TX, thiosultap-sodium + TX, tralomethrin + TX, transpermethrin + TC, triazamate + TC, trichlorometaphos-3 + TC, trichloronate + TC, trimetacarb + TC, tolprocarb + TC, trichloropyricarb + TC, triprene + TC, veratridine + TC, veratrine + TC, CMC + TC, zetamethrin + TC, zinc phosphide + TC, zolaprophos + TX, and meperfluthrin + TX, tetramethylfluthrin + TX, bis(tributyltin) oxide + TX, bromoacetamide + TX, iron(III) phosphate + TX, niclosamide-olamine + TX, tributyltin oxide + TX, pyrimorph + TX, trifenmorph + 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-thioxo-1,3,5-thiadiazinan-3-ylacetic acid + TX, 6-isopentenylaminopurine + TX, 2-fluoro-N-(3-methoxyphenyl)-9H-purine-6-amine + TX, benclotiase + TX, cytokinins + TX, DCIP + TX, furfural + TX, isamidophos + TX, kinetin + TX, compositions based on Myrothecium verrucaria + TX, tetrachlorothiophene + TX, xylenols + TX, zeatin + TX, potassium ethyl xanthate + TX, acibenzolar + TX, acibenzolar-v-methyl + TX, Reynoutria sachalinensis extract + TX, alpha-chlorohydrin + TX, antu + TX, barium carbonate + TX, bisthiosemium + TX, brodifacoum + TX, bromadiolone + TX, bromethalin + TX, chlorophacinone + TX, chole calciferol + TX, coumachlor + TX, coumafuril + TX, coumatetralyl + TX, crimidine + TX, difenacoum + TX, difethialone + TX, diphacinone + TX, ergocalciferol + TX, flocumafen + TX, fluoroacetamide + TX, flupropadine + TX, flupropadine hydrochloride + TX, norbormide + TX, fosacetim + TX, phosphorus + TX, pindone + TX, pyrinuron + TX, skilliroside + TX, sodium fluoroacetate + TX, thallium sulfate + TX, warfarin + TX, 2-(2-butoxyethoxy)ethylpiperonylate + TX, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone + TX, farnesol with nerolidol + TX, verbutin + TX, MGK 264 + TX, piperonyl butoxide + TX, piprotal + TX, propyl isomer + TX, S421 + TX, sesamex + TX, sesasmoline + TX, sulfoxide + TX, anthraquinone + TX, copper naphthenate + TX, copper oxychloride + TX, dicyclopentadiene + TX, thiram + TC, zinc naphthenate + TC, ziram + TC, imanin + TC, ribavirin + TC, chloroinconazide + TC, mercuric oxide + TC, methyl thiophanate + TC, azaconazole + TC, bitertanol + TC, bromuconazole + TC, cyproconazole + TC, difenoconazole + TC, diniconazole - + TX, epoxiconazole + TX, fenbuconazole + TX, fluquinconazole + TX, flusilazole + TX, flugriafol + TX, furamethpir + TX, hexaconazole + TX, imazalil + TX, imibenconazole + TX, ipconazole + TX, metconazole + TX, myclobutanil + TX, paclobutrazol + TX, pefurazoate + TX, penconazole + TX, prothioconazole + TX, pyrifenox + TX, prochloraz + TX, propiconazole + TX, pyrizoxazole + TX, simeconazole + TX, tebuconazole + TX, tetraconazole + TX, triadimefon + TX, triadimenol + TX, triflumizole + TX, triticonazole + TX, ancymidol + TX, fenarimol + TX, nuarimol + TX, bupirimol + TX, dimethirimol + TX, ethirimol + TX, dodemorph + TX, fenpropidine + TX, fenpropimorph + TX, spiroxamine + TX, tridemorph + TX, cyprodinil + TX, mepanipyrim + TX, pyrimethanil + TX, fenpiclonil + TX, fludioxonil + TX, benalaxyl + TX, furalaxyl + TX, metalaxyl + TX, metalaxyl-M + TX, ofuras + TX, oxadixil + TX, carbendazim + TX, debacarb + TX, fuberidazole - + TX, thiabendazole + TX, chlozolinate + TX, dichlozolin + TX, myclozolin- + TX, procymidone + TX, vinclozolin + TX, boscalid + TX, carboxin + TX, fenfuram + TX, flutolanil + TX, mepronil + TX, oxycarboxin + TX, penthiopyrad + TX, tifluzamide + TX, dodine + TX, iminoctadine + TX, azoxystrobin + TX, dimoxystrobin + TX, enestroburin + TX, phenaminestrobin + TX, flufenoxystrobin + TX, fluoxastrobin + TX, kresoxim-methyl + TX, metominostrobin + TX, trifloxystrobin + TX, orysastrobin + TX, picoxystrobin + TX, pyraclostrobin + TX, pyramethostrobin + TX, pyraoxystrobin + TX, ferbam + TX, mancozeb + TX, maneba + TX, metyram + TX, propineba + TX, cineba + TX, captafol + TX, captan + TX, fluoroimide + TX, folpeta + TX, tolylfluanide + TX, Bordeaux mixture + TX, copper oxide + TX, mancopper + TX, oxine copper + TX, nitrotal-isopropyl + TX, edifenphos + TX, iprobenphos + TX, phosdifene + TX, tolclofos-methyl + TX, anilazine + TX, benthiavalicarb + TX, blasticidin-S+ TX, chloroneba - + TX, chlorothalonil + TX, cyflufenamide + TX, cymoxanil + TX, cyclobutrifluram + TX, diclocimet + TX, diclomesine - + TX, dicloran + TX, dietofencarb + TX, dimethomorph - + TX, flumorph + TX, dithianone + TX, etaboxam + TX, etridiazole + TX, famoxadone + TX, fenamidone + TX, fenoxanil + TX, ferimzone + TX, fluazinam + TX, fluopicolide + TX, flusulfamide + TX, fluxapyroxad + TX, fenhexamide + TX, fosetyl-aluminum - + TX, chemexazole + TX, iprovalicarb + TX, cyazofamide + TX, metasulfocarb + TX, metrafenone + TX, pencicuron + TX, phthalide + TX, polyoxins + TX, propamocarb + TX, piribencarb + TX, proquinazide + TX, pyroquilone + TX, pyriophenone + TX, quinoxifene + TX, quintozene + TX, tiadinil + TX, triazoxide + TX, tricyclazole + TX, triforin + TX, validamycin + TX, valifenalate + TX, zoxamide + TX, mandipropamide + TX, flubenetram + TX, isopyrazam + TX, sedaxane + TX, benzovindiflupir + TX, pidiflumetofen + TX, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3',4',5'-trifluoro-biphenyl-2-yl)-amide + TX, isoflucipram + TX, isothianil + TX, dipimethicone + TX, 6-ethyl-5,7-dioxopyrrolo[4,5][1,4]dithiino[1,2-c]isothiazole-3-carbonitrile + TX, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethylindan-4-yl]pyridine-3-carboxamide + TX, 4-(2,6-difluorophenyl)-6-methyl-5-phenylpyridazine-3-carbonitrile + TX, (R)-3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide + TX, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-2,5-dimethylpyrazol-3-amine + TX, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine + TX, fluindapyr + TX, cumethoxystrobin (jiaxiangjunzhi) + TX, luibenimixianan + TX, dichlobenthiazox + TX, mandestrobin + TX, 3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1-yl)quinolone + TX, 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phenyl]propan-2-ol + TX, oxathiapiproline + TX, tert-butyl-N-[6-[[[(1-methyltetrazol-5-yl)-phenylmethylene]amino]oxymethyl]-2-pyridyl]carbamate + TX, pyraziflumide + TX, inpirfluxam + TX, trolprocarb + TX, mefentrifluconazole + TX, ipfentrifluconazole + TX, 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethylindan-4-yl]pyridin-3-carboxamide + TX, N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylformamidine + TX, N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethylphenyl]-N-ethyl-N-methylformamidine + TX, [2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]thiazol-4-yl]-4,5-dihydroisoxazol-5-yl]-3-chlorophenyl]methanesulfonate + TX, but-3-ynyl N-[6-[[Z)-[(1-methyltetrazol-5-yl)phenylmethylene]amino]oxymethyl]-2-pyridyl]carbamate + TX, methyl N-[[5-[4-(2,4-dimethylphenyl)triazol-2-yl]-2-methylphenyl]methyl]carbamate + TX, 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine + TX, pyridachloromethyl + 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-methylphenyl]-4-methyltetrazol-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, aminopyrifene + TX, amethoctradine + TX, amisulbrom + TX, penflufen + TX, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethylpent-3-enamide + TX, florylpicoxamide + TX, fenpicoxamide + TX, tebufloquine + TX, ipflufenoquine + TX, quinofumelin + TX, isofetamide + TX, N-[2-[2,4-dichlorophenoxy]phenyl]-3-(difluoromethyl)-1-methylpyrazole-4-carboxamide + TX, N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-1-methylpyrazole-4-carboxamide + TX, benzothiostrobin + TX, fenamacryl + TX, zinc salt 5-amino-1,3,4-thiadiazol-2-thiol (2:1) + TX, fluopyram + TX, flutianil + TX, fluopimomide + TX, pyrapropone + TX, picarbutrazox + TX, 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethylindan-4-yl)pyridin-3-carboxamide + TX, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridin-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, methyltetraprole + TX, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide + TX, α-(1,1-dimethylethyl)-α-[4'-(trifluoromethoxy)[1,1'-biphenyl]-4-yl]-5-pyrimidinemethanol + TX, fluoxapiproline + 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-sulfanyl-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-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, trinexapac + TX, kumoxystrobin + TX, zhongshenmycin + TX, copper thiodiazole + TX, zinc thiazole + TX, amectotractin + TX, iprodione + TX, N-octyl-N'-[2-(octylamino)ethyl]ethane-1,2-diamine + TX; N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxyethoxy]-3-pyridyl]-N-ethyl-N-methylformamidine + TX, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxyethoxy]-3-pyridyl]-N-ethyl-N-methylformamidine + TX, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxyethoxy)-3-pyridyl]-N-ethyl-N-methylformamidine + TX, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxyethoxy)-3-pyridyl]-N-isopropyl-N-methylformamidine + TX (these compounds can be prepared according to the methods described in WO 2015/155075); N'-[5-bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N-methylformamidine + TX (this compound can be prepared according to the methods described in IPCOM000249876D); N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenylethyl)phenyl]-N-methylformamidine + TX, N'-[4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxyethyl)-5-methoxy-2-methylphenyl]-N-isopropyl-N-methylformamidine + TX (these compounds can be obtained according to the methods described in WO 2018/228896); N-ethyl-N-[5-methoxy-2-methyl-4-[2-trifluoromethyl)oxetan-2-yl]phenyl]-N-methylformamidine + TX, N-ethyl-N'-[5-methoxy-2-methyl-4-[2-trifluoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methylformamidine + TX (these compounds can be obtained according to the methods described in WO 2019/110427); N-[(1R)-1-benzyl-3-chloro-1-methylbut-3-enyl]-8-fluoroquinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-3-chloro-1-methylbut-3-enyl]-8-fluoroquinoline-3-carboxamide + TX, N-[(1R)-1-benzyl-3,3,3-trifluoro-1-methylpropyl]-8-fluoroquinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-3,3,3-trifluoro-1-methylpropyl]-8-fluoroquinoline-3-carboxamide + TX, N-[(1R)-1-benzyl-1,3-dimethylbutyl]-7,8-difluoroquinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-1,3-dimethylbutyl]-7,8-difluoroquinoline-3-carboxamide + TX, 8-fluoro-N-[(1R)-1-[(3-fluorophenyl)methyl]-1,3-dimethylbutyl]quinoline-3-carboxamide + TX, 8-fluoro-N-[(1S)-1-[(3-fluorophenyl)methyl]-1,3-dimethylbutyl]quinoline-3-carboxamide + TX, N-[(1R)-1-benzyl-1,3-dimethylbutyl]-8-fluoroquinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-1,3-dimethylbutyl]-8-fluoroquinoline-3-carboxamide + TX, N-((1R)-1-benzyl-3-chloro-1-methylbut-3-enyl)-8-fluoroquinoline-3-carboxamide + TX, N-((1S)-1-benzyl-3-chloro-1-methylbut-3-enyl)-8-fluoroquinoline-3-carboxamide + TX (these compounds can be prepared according to the methods described in WO 2017/153380);

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 obtained according to the methods described in WO 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-dimethylisoquinoline + TX, 6-chloro-4,4-difluoro-3,3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline + TX, 4,4-difluoro-1-(5-fluoro-4-methylbenzimidazol-1-yl)-3,3-dimethylisoquinoline + TX, 3-(4,4-difluoro-3,3-dimethyl-1-isoquinolyl)-7,8-dihydro-6H-cyclopenta[e]benzimidazole + TX (these compounds can be prepared according to the methods described in WO 2016/156085); [(1S,2S)-1-methyl-2-(o-tolyl)propyl]-(2S)-2-[(3-hydroxy-4-methoxypyridin-2-carbonyl)amino]propanoate + TX, [(1S,2S)-1-methyl-2-(o-tolyl)propyl]-(2S)-2-[(3-acetoxy-4-methoxypyridin-2-carbonyl)amino]propanoate + TX, [(1S,2S)-1-methyl-2-(o-tolyl)propyl]-(2S)-2-[(4-methoxy-3-propanoyloxypyridine-2-carbonyl)amino]propanoate + TX, [(1S,2S)-2-(4-fluoro-2-methylphenyl)-1,3-dimethylbutyl]-(2S)-2-[(3-hydroxy-4-methoxypyridine-2-carbonyl)amino]propanoate + TX, [(1S,2S)-2-(4-fluoro-2-methylphenyl)-1,3-dimethylbutyl]-(2S)-2-[(3-acetoxy-4-methoxypyridine-2-carbonyl)amino]propanoate + TX, [(1S,2S)-2-(4-fluoro-2-methylphenyl)-1,3-dimethylbutyl]-(2S)-2-[(4-methoxy-3-propanoyloxypyridine-2-carbonyl)amino]propanoate + TX, N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide + TX, N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide + TX, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide + 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]methyl]urea + TX, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide + TX, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one + TX, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl] isoxazolidin-3-one + TX, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylate + 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 according to 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)propan-2-ol + TX (this compound can be obtained according to the methods described in WO 2017/029179); 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol + TX (this compound can be obtained according to the methods described in WO 2017/029179); 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile + TX (this compound can be obtained according to the methods described in WO 2016/156290); 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile + TX (this compound can be obtained according to the methods described in WO 2016/156290); (4-phenoxyphenyl)methyl 2-amino-6-methyl-pyridine-3-carboxylate + TX (this compound can be obtained according to the methods described in WO 2014/006945); 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetrona + TX (this compound can be prepared according to the methods described in WO 2011/138281); N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide + 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-dimethylpent-3-enamide + TX (this compound can be obtained according to the methods described in WO 2018/153707); N'-(2-chloro-5-methyl-4-phenoxyphenyl)-N-ethyl-N-methylformamidine + TX; N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylformamidine + TX (this compound can be obtained according to the methods described in WO 2016/202742); 2-(difluoromethyl)-N-[(3S)-3-ethyl-1,1-dimethylindan-4-yl]pyridine-3-carboxamide + TX (this compound can be obtained according to the methods described in WO 2014/095675); (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone + TX, (3-methylisoxazol-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone + TX (these compounds can be obtained according to the methods 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 obtained according to the methods described in WO 2018/065414); ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate + TX (this compound can be obtained according to the methods 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-methylcarbonimidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX (these compounds can be prepared according to the methods described in WO 2018/202428), a biostimulant containing organic carbon, Nutrients and Amino Acids (Quantis™) + TX.

References in square brackets following active ingredients, e.g. [3878-19-1], refer to the Chemical Abstracts Service registry number. The above-described ingredients are known for compounding. When active ingredients are included in The Pesticide Manual [The Pesticide Manual - A World Compendium; Thirteenth Edition; Editor: C. D. S. TomLin; British Crop Protection Council], they are described therein under the entry number given in parentheses above for the particular compound; e.g. the compound "abamectin" is described under registry number (1). When "[CCN]" is added to a particular compound above, the compound in question is included in the Compendium of Pesticide Common Names, which is available on the Internet [A. Wood; Compendium of Pesticide Common Names, Copyright © 1995-2004]; For example, the compound "acetoprole" is described at the Internet address http://www.alanwood.net/pesticides/acetoprole.html.

Most of the active ingredients described above are listed above in this document by the so-called "common name", which corresponds to the "ISO common name" or another "common name" in use in individual cases. If a designation is not the "common name", the nature of the designation used instead is given in parentheses for a particular compound; in this case the IUPAC name, the IUPAC/Chemical Abstracts Service name, the "chemical name", the "traditional name", the "compound name" or the "development code" is used or, if none of these designations nor the "common name" is used, the "alternative name" is used. "CAS Registry Number" means the Chemical Abstracts Service Registry Number.

In "illustrative" mixture-based compositions, the mixtures of compounds of formula (I) (selected from Table X (above)) with the active ingredients described above comprise a compound selected from Table X (above) and the active ingredient described above, preferably in a mixing ratio of from 100:1 to 1:100, in particular from 50:1 to 1:50, more in particular in a ratio of from 20:1 to 1:20, even more in particular from 10:1 to 1:10, even more in particular from 7.5:1 to 1:7.5, in particular from 5:1 to 1:5, particular preference is given to a ratio of from 2:1 to 1:2, and a ratio of from 4:1 to 2:1 is also preferred, in particular in a ratio of 1:1, or 5:1, or 5:2, or 5:3, or 5:4, or 4:1, or 4:2, or 4:3, or 3:1, or 3:2, or 2:1, or 1:5, or 2:5, or 3:5, or 4:5, or 1:4, or 2:4, or 3:4, or 1:3, or 2:3, or 1:2, or 1:600, or 1:300, or 1:150 or 1:35 or 2:35 or 4:35 or 1:75 or 2:75 or 4:75 or 1:6000 or 1:3000 or 1:1500 or 1:350 or 2:350 or 4:350 or 1:750 or 2:750 or 4:750. These mixing ratios are given by weight.

The compositions based on the mixtures described above (in accordance with the present invention and the "illustrative" compositions based on the mixtures) can be used in a method for providing control of pests, which comprises applying a composition containing the mixture described above to pests or their environment.

Mixtures containing a compound of formula (I) selected from Table X (above) and one or more active ingredients as described above can be used, for example, in the form of a separate "ready mix", in a combined spray mixture consisting of separate formulations of the individual components representing the active ingredients, such as a "tank mix", and in a combined application of the individual active ingredients, when applied in a sequential manner, i.e. one after the other over a suitably short period, such as several hours or days. The order of application of the compounds of formula (I) selected from Table X (above) and the active ingredients described above is not critical to the implementation of the present invention.

The compositions of the present invention can also be used to improve crops. 'Crop improvement' according to the present invention means improved plant vigor, improved plant quality, improved tolerance to stress factors and/or improved resource utilization.

According to the present invention, 'improving plant vigor' means that certain traits are improved qualitatively or quantitatively compared to the same trait in a control plant that was grown under the same conditions without using the method of the present invention. Such traits include, but are not limited to, earlier and/or improved germination, improved emergence, the ability to use fewer seeds, increased root growth, a more developed root system, increased root nodule formation, increased shoot growth, increased tillering, stronger shoots, more productive shoots, increased or improved plant density, less plant lodging, increased and/or improved plant height, increased plant weight (fresh or dry), larger leaf blades, greener leaf color, increased pigment content, increased photosynthetic activity, earlier flowering, longer panicles, earlier grain maturity, increased seed, fruit or pod size, increased pod or spike number, increased number of seeds per pod or spike, increased seed weight, increased seed filling, less lower leaf drop, delayed senescence, improved plant vigor, increased amino acid levels in storage tissues. and/or fewer inputs required (e.g., less fertilizer, water, and/or labor required). A plant with improved vigor may be characterized by an improvement in any of the above traits, or any combination, or two or more of the above traits.

According to the present invention, 'improving plant quality' means that certain traits are improved qualitatively or quantitatively compared to the same trait in a control plant that was grown under the same conditions without the use of the method of the present invention. Such traits include, but are not limited to, improved plant appearance, reduced ethylene (reduced formation and/or suppression of reception), improved quality of harvested material such as seeds, fruits, leaves, vegetables (such improved quality may manifest itself as improved appearance of harvested material), improved carbohydrate content (e.g., increased amounts of sugar and/or starch, improved sugar acid ratio, decreased amount of reducing sugars, increased sugar production rate), improved protein content, improved oil content and composition, improved nutritional value, decreased amount of non-nutritional compounds, improved organoleptic properties (e.g., improved palatability) and/or increased consumer health benefits (e.g., increased levels of vitamins and antioxidants)), improved post-harvest characteristics (e.g., increased shelf life and/or storage stability, easier suitability for chemical processing, easier extraction of compounds), more uniform crop development (e.g., synchronized germination, flowering and/or fruiting of plants) and/or improved seed quality (e.g. for use in subsequent seasons). A plant with improved quality may be characterized by an improvement in any of the above mentioned traits, or any combination, or two or more of the above mentioned traits.

According to the present invention, 'improved tolerance to stress factors' means that certain traits are improved qualitatively or quantitatively compared to the same trait in a control plant that was grown under the same conditions without applying the method of the present invention. Such traits include, but are not limited to, increased tolerance and/or resistance to abiotic stress factors that cause sub-optimal growing conditions, such as drought (e.g., any stress that results in a deficiency of water content in plants, insufficient water uptake potential, or a decrease in water supply to plants), cold stress, heat stress, osmotic stress, UV stress, flooding, increased salinity (e.g., in soil), increased mineral stress, ozone stress, exposure to strong light, and/or limited nutrient availability (e.g., nitrogen-containing and/or phosphorus-containing nutrients). A plant with improved tolerance to stress factors may be characterized by an improvement in any of the above-mentioned traits, or any combination, or two or more of the above-mentioned traits. In the case of drought and nutrient stress, such improved tolerance values may be due to, for example, more efficient uptake, application, or retention of water and nutrients.

According to the present invention, 'improved resource utilization' means that plants are able to grow more efficiently using given levels of resources compared to the growth of control plants that are grown under the same conditions without using the method of the present invention. In particular, resources include, but are not limited to, fertilizer (such as nitrogen, phosphorus, potassium, micronutrients), light and water. A plant with an improved resource utilization may be characterized by improved use of any of the above-mentioned resources or any combination of two or more of the above-mentioned resources.

Other improvements to crops according to the present invention include reduction in plant height or reduction in tillering, which are preferred crop properties, or conditions under which it is desirable to produce less biomass and less tillering.

Any or all of the above crop improvements may result in improved crop yield by improving, for example, plant physiology, plant growth and development, and/or plant architecture. In the context of the present invention, the term "yield" includes, but is not limited to, (i) an increase in the rate of biomass production, grain yield, starch content, oil content, and/or protein content, which may result from (a) an increase in the amount produced by the plant per se or (b) an improved ability to harvest plant material, (ii) an improvement in the composition of the harvestable material (e.g., improved sugar acid ratios, improved oil composition, increased nutritional value, decreased non-nutritional compounds, increased consumer health benefits), and/or (iii) an increased/easier harvestability of the crop, improved suitability for processing the crop, better storage stability/increased shelf life. Increased yield of an agricultural plant means that, with the possibility of performing a quantitative measurement, the yield of the product of the corresponding plant is increased by a measurable amount compared to the yield of the same plant product obtained under the same conditions, but without using the present invention. According to the present invention, it is preferable that the yield is increased by at least 0.5%, more preferably by at least 1%, even more preferably by at least 2%, wherein more preferably by at least 4%, preferably by 5% or even more.

Any or all of the above crop improvements may also result in more efficient land use, i.e. land that was previously inaccessible or suboptimal for cultivation may become available. For example, plants that exhibit increased ability to survive drought conditions may be cultivated in areas with suboptimal rainfall, such as those that may border or even be in a desert.

In one aspect of the present invention, improvements to the agricultural crop are carried out in the substantial absence of pests and/or diseases and/or stress caused by abiotic factors. In a further aspect of the present invention, improvements in plant vigor, stress tolerance, quality and/or yield are carried out in the substantial absence of pests and/or diseases. For example, pests and/or diseases can be controlled by pesticide treatments applied prior to or simultaneously with the method of the present invention. In yet another further aspect of the present invention, improvements in plant vigor, stress tolerance, quality and/or yield are carried out in the absence of pests and/or diseases. In a further embodiment, improvements in plant vigor, quality and/or yield are carried out in the absence or substantial absence of stress caused by abiotic factors.

The compositions of the present invention can also be used in the field of protecting stored goods from fungal attack. According to the present invention, the term "stored goods" is understood as meaning natural substances of plant and/or animal origin and their processed forms, which have been taken from the natural life cycle and for which long-term protection is required. Stored goods of plant origin, such as plants or parts thereof, for example petioles, leaves, tubers, seeds, fruits or grains, can be protected in a freshly harvested state or in a processed form, such as pre-dried, moistened, finely ground, ground, pressed or roasted. Also falling within the definition of stored goods are sawn timber, either in the form of unprocessed sawn timber, such as building timber, power transmission line poles and fencing, or in the form of finished products, such as furniture or objects made of wood. Stored goods of animal origin are skins, leather, furs, hair, etc. The composition according to the present invention can prevent adverse effects such as rotting, discoloration or mold. Preferably, the term "stored goods" is understood as meaning natural substances of plant origin and/or their processed forms, more preferably fruits and their processed forms, such as pome fruits, stone fruits, berry fruits and citrus fruits, as well as their processed forms. In another preferred embodiment of the present invention, the term "stored goods" is understood as meaning wood.

Accordingly, a further aspect of the present invention is a method for protecting a stored commodity which comprises applying to the stored commodity a composition according to the present invention.

The composition according to the present invention can also be used in the field of protecting technical material from fungal attack. According to the present invention, the term "technical material" includes paper; carpets; buildings; cooling and heating systems; facing boards; ventilation and air conditioning systems, etc.; preferably, the term "technical material" is understood as meaning facing boards. The composition according to the present invention can prevent adverse effects such as rotting, discoloration or mold.

The composition according to the present invention is generally formulated in various ways using formulation auxiliaries such as carriers, solvents and surfactants. The formulations can be presented in various physical forms, for example in the form of sprayable powders, gels, wettable powders, water-dispersible granules, water-dispersible tablets, effervescent dragees, emulsifiable concentrates, microemulsion concentrates, oil-in-water emulsions, oil flowables, aqueous dispersions, oil dispersions, suspoemulsions, 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 forms known, for example, from the Manual on Development and Use of FAO and WHO Specifications for Pesticides, United Nations, First Edition, Second Revision (2010). Such formulations can either be applied directly or diluted before application. Dilutions can be made, for example, with water, liquid fertilizers, micronutrients, biological organisms, oil or solvents.

The formulations can be prepared, for example, by mixing the active ingredient with formulation excipients to obtain compositions in the form of finely divided solids, granules, solutions, dispersions or emulsions. The active ingredients can also be formulated with other excipients, such as finely divided solids, mineral oils, vegetable or animal oils, modified vegetable or animal oils, organic solvents, water, surfactants or combinations thereof.

The active ingredients can also be contained in microcapsules. The microcapsules contain the active ingredients in a porous carrier. This allows the active ingredients to be released into the environment in controlled amounts (e.g. slow release). The microcapsules typically have a diameter of 0.1 to 500 microns. They contain the active ingredients in an amount of about 25 to 95% by weight of the capsule weight. The active ingredients can be in the form of a monolithic solid, in the form of fine particles in a solid or liquid dispersion or in the form of a suitable solution. The encapsulating membranes can contain, for example, natural and synthetic rubbers, cellulose, styrene-butadiene copolymers, polyacrylonitrile, polyacrylate, polyesters, polyamides, polyureas, polyurethane or chemically modified polymers and starch xanthates or other polymers known to those skilled in the art. Alternatively, very small microcapsules can be produced in which the active ingredient is contained as finely dispersed particles in a solid matrix of the base material, but the microcapsules themselves are not encapsulated.

Formulation aids which are suitable for preparing the compositions according to the present invention are known per se. Liquid carriers that can be used include water, toluene, xylene, petroleum ether, vegetable oils, acetone, methyl ethyl ketone, cyclohexanone, acid anhydrides, acetonitrile, acetophenone, amyl acetate, 2-butanone, butylene carbonate, chlorobenzene, cyclohexane, cyclohexanol, alkyl esters of acetic acid, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, alkylpyrrolidone, Ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1,1,1-trichloroethane, 2-heptanone, alpha-pinene, d-limonene, ethyl lactate, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, gamma-butyrolactone, glycerin, glycerol acetate, glycerol diacetate, glycerol triacetate, hexadecane, hexylene glycol, isoamyl acetate, isobornyl acetate, isooctane, isophorone, isopropyl benzene, isopropyl myristate, lactic acid, lauryl amine, mesityl oxide, methoxypropanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, methylene chloride, m-xylene, n-hexane, n-octylamine, octadecanoic acid, octylamine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol, propionic acid, propyl lactate, propylene carbonate, propylene glycol, propylene glycol methyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylene sulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol methyl ether, diethylene glycol methyl ether, methanol, ethanol, isopropanol and high molecular weight alcohols such as amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, ethylene glycol, propylene glycol, glycerin, N-methyl-2-pyrrolidone, etc.

Suitable solid carriers are, for example, talc, titanium dioxide, pyrophyllite clay, silicon dioxide, attapulgite clay, kieselguhr, limestone, calcium carbonate, bentonite, calcium montmorillonite, cottonseed husks, wheat flour, soybean flour, pumice, wood flour, ground walnut shells, lignin and the like.

A large number of surfactants can be used successfully in both solid and liquid formulations, especially in those formulations that can be diluted with a carrier before use. The surfactants may be anionic, cationic, nonionic or polymeric, and they can be used as emulsifiers, wetting agents or suspending agents or for other purposes. Typical surfactants include, for example, alkyl sulfate salts such as diethanolammonium lauryl sulfate, alkyl aryl sulfonate salts such as calcium dodecylbenzenesulfonate, alkyl phenol/alkylene oxide addition products such as nonylphenol ethyl oxylate, alcohol/alkylene oxide addition products such as tridecyl alcohol ethoxylate, soaps such as sodium stearate, alkyl naphthalene sulfonate salts such as sodium dibutyl naphthalene sulfonate, dialkyl esters of sulfosuccinate salts such as sodium di(2-ethylhexyl) sulfosuccinate, sorbitan esters such as sorbitol oleate, quaternary amines such as lauryl trimethyl ammonium chloride, polyethylene glycol esters of fatty acids such as polyethylene glycol stearate, block copolymers of ethylene oxide and propylene oxide and salts mono- and dialkyl phosphate esters, as well as additional substances described, for example, in McCutcheon's Detergents and Emulsifiers Annual, MC Publishing Corp., Ridgewood New Jersey (1981).

Additional excipients that may be used in pesticide formulations include crystallization inhibitors, viscosity modifiers, suspending agents, colorants, antioxidants, foaming agents, light absorbers, mixing aids, antifoams, complexing agents, neutralizing or pH modifying agents and buffers, corrosion inhibitors, fragrances, wetting agents, absorption enhancers, micronutrients, plasticizers, glidants, lubricants, dispersants, thickeners, antifreezes, microbicides, and liquid and solid fertilizers.

The compositions according to the present invention may contain an additive containing an oil of vegetable or animal origin, a mineral oil, alkyl esters of such oils or mixtures of such oils and oil derivatives. The amount of oil additive in the composition according to the present invention is usually from 0.01 to 10% based on the amount of the mixture to be used. For example, the oil additive can be added to the sprayer tank at the desired concentration after the mixture for spraying has been prepared. Preferred oil additives contain mineral oils or an oil of vegetable origin, for example, rapeseed oil, olive oil or sunflower oil, emulsified vegetable oil, alkyl esters of oils of vegetable origin, for example methyl derivatives, or an oil of animal origin, such as fish oil or beef tallow. Preferred oil additives comprise alkyl esters of _C8 - _C22 fatty acids, in particular methyl derivatives of _C8 - _C18 fatty acids, such as methyl esters of lauric acid, palmitic acid and oleic acid (methyl laurate, methyl palmitate and methyl oleate, respectively). Many oil derivatives are known from Compendium of Herbicide Adjuvants, ^10th Edition, Southern Illinois University, 2010.

The compositions typically contain from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight of the compounds of component (A) and component (B) and from 1 to 99.9% by weight of a formulation aid, which preferably contains from 0 to 25% by weight of a surfactant. Since commercial products can preferably be formulated as concentrates, the end user will typically use diluted compositions.

Application rates vary widely and are dependent on soil properties, method of application, crop plant, pest to be controlled, prevailing climatic conditions and other factors determined by the method of application, time of application and target crop. As a general guide, compounds can be applied at rates of 1 to 2000 l/ha, in particular 10 to 1000 l/ha.

Certain mixture-based compositions containing a compound of formula (I) as described above may exhibit a synergistic effect. A synergistic effect is observed whenever the effectiveness of a combination of active ingredients is greater than the combined effectiveness of the individual components. The calculated effectiveness E for a given combination of active ingredients follows the so-called Colby formula and may be calculated as follows (COLBY, S.R. "Calculating synergistic and antagonistic responses of herbicide combination". Weeds, Vol. 15, pp. 20-22; 1967):

ppm = milligrams of active ingredient (=a.i.) per liter of spray mixture,

X = % effectiveness of the active ingredient (A) when using p ppm active ingredient,

Y = % efficiency of the active ingredient (B) when q ppm of the active ingredient is applied.

According to Colby's formula, the expected (additive) effectiveness of active ingredients (A)+(B) in the case of using p+q ppm of active ingredient is:

If the actually observed efficiency (O) is greater than the calculated efficiency (E), then the efficiency of the combination is superadditive, i.e. a synergistic effect is observed. In mathematical expression, synergism corresponds to a positive value of the difference (O-E). In the case of only additional addition of activity indicators (calculated activity), the said difference (O-E) is equal to zero. A negative value of the said difference (O-E) indicates a loss of activity compared to the calculated activity.

However, in addition to the actual synergistic effect with respect to fungicidal activity, the composition according to the present invention may also be characterized by additional unexpected advantageous properties. Examples of such advantageous properties that can be mentioned are more effective degradability; improved toxicological and/or ecotoxicological properties; improved characteristics of useful plants, including germination, crop yield, more developed root system, increased shoot formation, increased plant height, larger leaf blade, less wilting of the main leaves, stronger shoots, greener leaf color, less need for fertilizers, less need for seed quantity, more productive shoots, earlier flowering, earlier grain maturity, less "falling" of plants (lodging), increased seedling growth, increased plant vigor and early germination.

The composition according to the present invention can be applied to phytopathogenic microorganisms, useful plants, their growing place, their propagation material, stored goods or technical materials that are at risk of being attacked by microorganisms.

The composition according to the present invention can be applied before or after inoculation of useful plants, their propagation material, stored goods or technical materials with microorganisms.

The amount in which the composition according to the present invention is applied will depend on various factors, such as the compounds used; the object of treatment, such as plants, soil or seeds; the type of treatment, such as spraying, dusting or seed dressing; the purpose of the treatment, such as preventive or therapeutic; the type of fungus to be controlled or the time of application.

When applied to useful plants, component (A) is generally applied at a rate of 5 to 2000 g a.i./ha, in particular, 10 to 1000 g a.i./ha, for example, 50, 75, 100 or 200 g a.i./ha, as a rule, together with 1 to 5000 g a.i./ha, in particular, 2 to 2000 g a.i./ha, for example, 100, 250, 500, 800, 1000, 1500 g a.i./ha of component (B).

In agricultural practice, the application rates of the composition according to the present invention depend on the type of effect desired and, as a rule, are in the range from 20 to 4000 g of the total composition per hectare.

If the composition according to the present invention is used for treating seeds, then in general, rates of from 0.001 to 50 g of the compound as component (A) per kg of seed, preferably from 0.01 to 10 g per kg of seed, and from 0.001 to 50 g of the compound as component (B) per kg of seed, preferably from 0.01 to 10 g per kg of seed, are sufficient.

For the avoidance of doubt, where a literature reference, patent application or patent is cited in the text of this application, the full text of the cited citation is incorporated herein by reference.

EXAMPLES

The following examples serve to illustrate the present invention.

The compounds (and compositions) of the present invention can be distinguished from known compounds (and compositions) by their greater effectiveness at low application rates, as will be demonstrated by one skilled in the art using the experimental procedures set forth in the Examples, using lower application rates if necessary, for example, 50 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1.5 ppm or 0.2 ppm of the active ingredient(s).

Throughout this description, temperatures are given in degrees Celsius, and "m.p." means melting point. LC/MS means liquid chromatography with mass spectrometry, and the description of the apparatus and methods are as follows.

Method G

The spectra were recorded on a Waters mass spectrometer (SQD single quadrupole mass spectrometer, SQDII) equipped with an electrospray source (polarity: positive and negative ions), capillary voltage: 3.00 kV, cone voltage range: 30 V, extractor voltage: 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: 100-900 Da) and an Acquity UPLC from Waters: two-component pump, heated column compartment, diode array detector, and ELSD detector. Column: Waters UPLC HSS T3, 1.8 μm, 30×2.1 mm, temperature: 60°C, wavelength range DAD (nm): 210-500; solvent gradient: A = water + 5% MeOH + 0.05% HCOOH, B = acetonitrile + 0.05% HCOOH; gradient: 10-100% B in 1.2 min; flow rate (ml/min) 0.85.

Method H

The spectra were recorded on a Waters mass spectrometer (SQD single quadrupole mass spectrometer, SQDII) equipped with an electrospray source (polarity: positive and negative ions), capillary voltage: 3.00 kV, cone voltage range: 30 V, extractor voltage: 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: 100-900 Da) and an Acquity UPLC from Waters: two-component pump, heated column compartment, diode array detector, and ELSD detector. Column: Waters UPLC HSS T3, 1.8 μm, 30×2.1 mm, temperature: 60°C, wavelength range DAD (nm): 210-500; solvent gradient: A = water + 5% MeOH + 0.05% HCOOH, B = acetonitrile + 0.05% HCOOH; gradient: 10-100% B in 2.7 min; flow rate (ml/min) 0.85.

If desired, enantiomerically pure final compounds can be obtained from racemic materials by appropriate standard physical separation techniques, such as chiral reversed-phase chromatography, or by stereoselective synthetic techniques, such as by using chiral starting materials.

Examples of compositions

The active ingredient is thoroughly mixed with the excipients and the mixture is thoroughly ground in a suitable mill to obtain wettable powders which can be diluted with water to obtain suspensions of the desired concentration.

The active ingredient is thoroughly mixed with the excipients and the mixture is thoroughly ground in a suitable mill to obtain powders that can be used directly for seed treatment.

Emulsifiable concentrate

active ingredients [components (A) and (B)] 10% polyethylene glycol octylphenol ether (4-5 mol ethylene oxide) 3% calcium dodecylbenzenesulfonate 3% simple polyglycol ether of castor oil (35 mol ethylene oxide) 4% cyclohexanone 30% xylene mixture 50%

From this concentrate, by diluting with water, it is possible to obtain emulsions of any required dilution, which can be used to protect plants.

Ready-to-use dust preparations are obtained by mixing the active ingredient with a carrier and grinding the mixture in a suitable mill. Such powders can also be used for dry seed dressing.

Extruded granules

active ingredients [components (A) and (B)] 15% sodium lignosulfonate 2% carboxymethylcellulose 1% kaolin 82%

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

Coated granules

active ingredients [components (A) and (B)] 8% polyethyleneglycol (molecular weight 200) 3% kaolin 89%

The finely ground active ingredient is applied uniformly to the moistened polyethylene glycol kaolin in a mixing device. In this way, non-dusting coated granules are obtained.

Suspension concentrate

active ingredients [components (A) and (B)] 40% propylene glycol 10% nonylphenol polyethylene glycol ether (15 mol ethylene oxide) 6% sodium lignosulfonate 10% carboxymethylcellulose 1% silicone oil (as a 75% emulsion in water) 1% water 32%

The finely ground active ingredient is thoroughly mixed with the excipients to form a suspension concentrate, from which suspensions of any desired degree of dilution can be obtained by diluting with water. Using such diluted solutions, living plants and plant propagation material can be treated and protected from contamination by microorganisms by spraying, watering or immersion.

Flowable concentrate for seed treatment

active ingredients [components (A) and (B)] 40% propylene glycol 5% copolymer of butanol and PO/EO 2% tristyrenephenol with 10-20 mol EO 2% 1,2-benzisothiazolin-3-one (as a 20% solution in water) 0.5% calcium salt of monoazo pigment 5% silicone oil (as a 75% emulsion in water) 0.2% water 45.3%

The finely ground active ingredient is thoroughly mixed with the excipients to form a suspension concentrate, from which suspensions of any desired degree of dilution can be obtained by diluting with water. Using such diluted solutions, living plants and plant propagation material can be treated and protected from contamination by microorganisms by spraying, watering or immersion.

Slow release capsule suspension

28 parts of the active ingredient combination [components (A) and (B)] are mixed with 2 parts of an aromatic solvent and 7 parts of a toluene diisocyanate/polymethylene polyphenyl isocyanate mixture (8:1). This mixture is emulsified in a mixture of 1.2 parts of polyvinyl alcohol, 0.05 parts of an antifoam and 51.6 parts of water until the particles of the required size are obtained. To this emulsion is added a mixture of 2.8 parts of 1,6-diaminohexane in 5.3 parts of water. The mixture is stirred until the polymerization reaction is complete. The resulting capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersing agent. The composition of the capsule suspension contains 28% of the active ingredients. The average diameter of the capsules is 8-15 microns. The resulting composition is applied to the seeds as an aqueous suspension in a device suitable for this purpose.

List of abbreviations

aq. = aqueous

br s = wide singlet

°C = degrees Celsius

DCM = dichloromethane

dd = doublet of doublets

DMF = dimethylformamide

DMSO = dimethyl sulfoxide

DMSO-d ₆ = deuterated dimethyl sulfoxide

d = doublet

EtOAc = ethyl acetate

eq. = equivalent

h. = hour(hours)

M = molar

m = multiplet

min = minutes

MHz = megahertz

m.p. = melting point

Pd ₂ (dba) ₃ = tris(dibenzylideneacetone)dipalladium(0)

Pd(dppf)Cl ₂ •DCM=[1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II), cDCM complex

Pd(PPh ₃ ) ₂ Cl ₂ = bis(triphenylphosphine)palladium(II) dichloride

ppm = parts per million

r.t. = room temperature

R _t = retention time

s = singlet

t = triplet

THF = tetrahydrofuran

LC/MS = liquid chromatography with mass spectrometry (description of the apparatus and methods used for LC/MS analysis are given above)

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

Examples of receipt

Example 1. This example illustrates the preparation of methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxyprop-2-enoate (compound X.04).

Step 1. Obtaining methyl 2-(5-bromo-2-methylphenoxy)acetate

To a solution of 5-bromo-2-methylphenol (53.47 mmol, 10.00 g) and methyl 2-bromoacetate (1.5 equiv., 80.20 mmol, 12.27 g, 7.44 mL) in tetrahydrofuran (0.5 mol/L, 106.9 mL) at room temperature was added potassium carbonate (2 equiv., 106.9 mmol, 14.78 g), and the light brown suspension was heated to 65 °C for 2 h and then allowed to cool 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 layer was washed with water, brine, dried over _Na2SO4 , filtered and concentrated in vacuo 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 carried directly to the next step without further purification.

LCMS (method H), Rt=1.59 min, MS: (M+1)=259, 261; ^1H NMR (400 MHz, CDCl ₃ ) δ ppm 2.25 (s, 3H) 3.84 (s, 3H) 4.66 (s, 2H) 6.84 (d, 1H) 7.05 (m, 2H)

Step 2. Obtaining methyl (Z)-2-(5-bromo-2-methylphenoxy)-3-methoxyprop-2-enoate

Part 1. To a solution of 2-(5-bromo-2-methylphenoxy)acetate (20.8 g, 80.3 mmol) and methyl formate (6.0 equiv., 482 mmol, 29.5 g, 30.5 mL) in tetrahydrofuran (0.5 mol/L, 161 mL) at room temperature under argon was added sodium methoxide (20 equiv., 161 mmol, 9.13 g) portionwise. The reaction was slightly exothermic and its temperature was maintained below 30 °C using a room temperature water bath. The reaction mixture was stirred at room temperature for 1 h and quenched by slow addition of saturated aqueous NaHCO ₃ solution. The two phases were separated and the aqueous phase was extracted with EtOAc. The combined organic layer was washed with saturated aqueous _NaHCO3 , brine, dried _{over Na2SO4} , filtered and concentrated in vacuo to give methyl 2-(5-bromo-2-methylphenoxy)-3-hydroxyprop-2-enoate, which was directly carried on to the next step without further purification.

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

Part 2. To a solution of crude methyl 2-(5-bromo-2-methylphenoxy)-3-hydroxyprop-2-enoate and dimethyl sulfate (1.2 eq., 93.2 mmol, 11.8 g, 8.8 mL) in DMF (0.5 mol/L, 155 mL) at room temperature under argon was added potassium carbonate (1.5 eq., 117 mmol, 16.3 g) 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 combined organic layer was washed with saturated aqueous _NaHCO3 , brine, dried with _Na2SO4 , filtered and concentrated in vacuo. The residue was purified by flash chromatography (cyclohexane:EtOAc) to give methyl (Z)-2-(5-bromo-2-methylphenoxy)-3-methoxyprop-2-enoate (59.6 mmol, 18.0 g, 75% yield) as an off-white solid.

LCMS (method G), Rt=1.02 min, MS: (M+1)=301, 303; ¹ H NMR (400 MHz, _CDCl3 ) δ ppm 2.31 (s, 3H) 3.74 (s, 3H) 3.91 (s, 3H) 6.86 (d, 1H) 7.05 (m, 2H) 7.35 (s, 1H)

Step 3. Preparation of methyl (Z)-2-[5-(cyclohexen-1-yl)-2-methylphenoxy]-3-methoxyprop-2-enoate

To a solution of methyl (Z)-2-(5-bromo-2-methylphenoxy)-3-methoxyprop-2-enoate (203 mg, 0.67 mmol, 1.00 equiv) in 1,4-dioxane (6 mL) and water (1 mL) were added cyclohexen-1-ylboronic acid (93.4 mg, 0.74 mmol, 1.10 equiv), potassium phosphate (295 mg, 1.35 mmol, 2.00 equiv), and X Phos Pd G2 (53.0 mg, 0.07 mmol, 0.10 equiv). The reaction mixture was stirred at 100 °C for 15 min and the heat source was removed. After reaching rt, the mixture was diluted with EtOAc and saturated aqueous _NaHCO3 solution, then extracted with EtOAc. The combined organic fraction was washed with saturated aqueous _NaHCO3 solution and brine, dried over _Na2SO4 , filtered and concentrated in _vacuo . The residue was purified by flash chromatography (cyclohexane:EtOAc) to give methyl (Z)-2-[5-(cyclohexen-1-yl)-2-methylphenoxy]-3-methoxyprop-2-enoate as an amorphous solid. LC-MS (Method G), Rt=1.17 min, MS: (M+H)=303; ¹ H NMR (400 MHz, CDCl ₃ ) δ ppm 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).

Step 4. Preparation of methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxyprop-2-enoate (compound X.04)

To a solution of methyl (Z)-2-[5-(cyclohexen-1-yl)-2-methylphenoxy]-3-methoxyprop-2-enoate (132 mg, 0.44 mmol, 1.00 equiv) in hexane (0.87 mL) and EtOAc (2.18 mL) was added palladium on carbon (23.2 mg, 0.01 mmol, 0.02 equiv). The reaction mixture was stirred under hydrogen atmosphere for 2 days. The reaction mixture was filtered through celite and concentrated in vacuo. The resulting crude residue was purified by flash chromatography (cyclohexane:EtOAc) to give methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxyprop-2-enoate as a white solid (mp: 131-132°C).

LC-MS (Method G), Rt=1.21 min, MS: (M+H)=305; ¹ H NMR (400 MHz, CDCl ₃ ) δ ppm 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).

Example 2. This example illustrates the preparation of methyl (Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxyprop-2-enoate (compound X.02)

Under argon, 1 M zinc chloride in THF (2.54 mmol) was added to 2 M cyclopentylmagnesium bromide in THF (2.54 mmol) and the pale yellow suspension was stirred at rt for 10 min, during which time a slight exotherm was observed. Then a solution of methyl (Z)-2-(5-bromo-2-methylphenoxy)-3-methoxyprop-2-enoate (0.153 g, 0.51 mmol) in tetrahydrofuran (2.5 mL) and PdCl ₂ (dppf) (0.19 g, 0.025 mmol) was added and the pale yellow suspension was heated at 50 °C for 3 h. The reaction mixture was then brought to rt, quenched with saturated aqueous _NH4Cl and extracted with tert-butyl methyl ether. The combined organic fraction was then washed with water and brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting crude residue was purified by flash chromatography (hexane:EtOAc gradient cycle) to afford 0.106 mg of the title compound as a white solid (mp 80-83 °C).

DS-bY (Method P)b Ke=1b16 minb bjj (M+H)=291zh ¹ P NMR (400 MHzb SVSd ₃ ) δ ззьж 7b35 (ыб 1Р)b 7b09 (вб 1Р)b 6b82 (вб 1Р)b 6b60 (ыб 1Р)b 3b90 (yb 3H)b 3b72 (yb 3H)b 2b91 (yb 1R)b 2b32 (yb 3H)b 2b10-1b97 (yb 2H)b 1b85-1b75 (yb 2H)b 1b74-1b65 (yb 2H)b 1b60-1b45 (b 2N)yu

Using the synthetic procedures described both above and below, compounds of formula (I) can be prepared accordingly.

If desired, enantiomerically pure final compounds can be obtained from racemic materials by appropriate standard physical separation techniques, such as chiral reversed-phase chromatography, or by stereoselective synthetic techniques (e.g., by using chiral starting materials).

BIOLOGICAL EXAMPLES

General examples of leaf disc tests using well plates.

Leaf discs or leaf segments of different plant species are cut from greenhouse-grown plants. The cut leaf discs or segments are placed in multiwell plates (24-well format) on water agar. The leaf discs are sprayed with the test solution before (preventatively) or after (curatively) inoculation. The compounds to be tested are prepared as solutions in DMSO (max. 10 mg/ml), which are diluted to the appropriate concentration of 0.025% Tween20 immediately before spraying. The inoculated leaf discs or segments are incubated under the specified conditions (temperature, relative humidity, light, etc.) in accordance with the respective test system. A separate assessment of the disease level is carried out depending on the pathosystem 3-14 days after inoculation. The disease control value is then calculated as a percentage relative to the untreated control leaf discs or segments.

General examples of liquid culture tests using well plates.

Fungal mycelial fragments or conidial suspensions, either freshly obtained from liquid cultures of the fungus or from cryostorage, are mixed directly with nutrient broth. Solutions of the test compound in DMSO (max. 10 mg/ml) are diluted 50-fold with 0.025% Tween20 and 10 µl of this solution are dispensed into a microtiter plate (96-well format). Nutrient broth containing fungal spores/mycelial fragments is then added to obtain the final concentration of the test compound. The test plates are incubated in the dark at 24°C and a relative humidity of 96%. Inhibition of fungal growth is determined photometrically after 2-7 days, depending on the pathosystem, and the percentage of antifungal activity relative to the untreated control is calculated.

Example A1. Fungicidal activity against Puccinia reconduct f. sp. tritici/wheat/treatment to prevent leaf disc infection (brown rust)

Wheat leaf segments were placed on agar in multiwell plates (24-well format) and sprayed with test solutions. After drying, the leaf segments were inoculated with a suspension of fungal spores. After appropriate incubation, the activity of the compound was assessed 8 dpi (days after inoculation) for preventive fungicidal activity.

The following compounds provided at least 80% control of Puccinia reconduct f. sp. tritici at 200 ppm compared to the untreated control, which showed extensive disease development under the same conditions:

Connections (from table T1): X.01, X.02, X.03, X.04

Example A2. Fungicidal activity against Puccinia reconduct f. sp. tritici/wheat/treatment for leaf disc infestation (brown rust)

Wheat leaf segments were plated on agar in multiwell plates (24-well format). The leaf segments were inoculated with the fungal spore suspension and sprayed with the test solutions 1 day after inoculation. After appropriate incubation, the compound activity was assessed 8 dpi for curative fungicidal activity. The following compounds provided at least 80% control of Puccinia recondita f. sp. tritici at 200 ppm compared to the untreated control, which showed extensive disease development under the same conditions:

Connections (from table T1): X.01, X.02, X.04

Example A3. Fungicidal activity against Phakopsora pachyrhizi/soybean/treatment to prevent leaf disc infection (Asian soybean rust)

Soybean leaf discs are placed on agar in multi-well plates (24-well format) and sprayed with test solutions. After drying, the leaf discs are inoculated with a suspension of fungal spores. After appropriate incubation, the activity of the compound is assessed at approx. 12 dpi (days after inoculation) for preventive fungicidal activity.

The following compounds provided at least 70% control of Phakopsora pachyrhizi at 60 ppm when compared to untreated controls which showed extensive disease development under the same conditions:

Connections (from table T1): X.01, X.02, X.03, X.04

Example A4. Fungicidal activity against Glomerella lagenarium (Colletotrichum lasenahum) liquid culture/cucumber/treatment to prevent infection (anthracnose)

Fungal conidia from cryogenic storage were directly mixed with nutrient broth (potato dextrose broth, PDB). A solution of test compounds in DMSO was added to a microtiter plate (96-well format) and nutrient broth containing fungal spores was added to it. The test plates were incubated at 24°C and growth inhibition was determined photometrically after 72 h at 620 nm.

The following compounds provided at least 80% control of Glomerella lagenarium at 20 ppm when compared to an untreated control that showed extensive disease development under the same conditions:

Connections (from table T1): X.01, X.02, X.03, X.04

Comparative data

The biological activity of the compounds X.02 and X.04 of the present invention was compared with the reference compounds Z-1 and Z-2. The reference compounds Z-1 and Z-2 are specifically disclosed on page 16 of WO 98/03464 and page 6 of EP 0212859, respectively.

Example B. Comparative biological activity against Puccinia recondita (brown rust), treatment

Method. Wheat leaf segments were placed on agar in multiwell plates (24-well format). The leaf segments were inoculated with a suspension of fungal spores and sprayed with the test solutions 1 day after inoculation. After appropriate incubation, the activity of the compound was assessed 8 dpi (days after inoculation) for treatment-promoting fungicidal activity.

Data are presented as disease control rates, expressed as percentages, for each compound for the bioassays and test standards described below in Table B1.

Further examples of biological tests relating to fungicidal compositions containing a mixture of components (A) and (B) as active ingredients.

Example C1. Fungicidal activity against Mycosphaerella arachidis syn.

Cercospora arachidicola

(brown leaf spot)

Fungal conidia from cryogenic storage were directly mixed with nutrient broth (potato dextrose broth, PDB). A solution of test compounds in DMSO was added to a microtiter plate (96-well format) and nutrient broth containing fungal spores was added to it. The test plates were incubated at 24°C and growth inhibition was determined photometrically after about 5-6 days at 620 nm.

The following compound mixtures provided at least 80% control of Mycosphaerella arachidis at the rates given in the table, compared to untreated controls under the same conditions that demonstrated extensive disease development.

The following formulations of the mixtures at the concentrations (in ppm) described in Tables C1-3 and C1-4 provided the following disease control in this test against Mycosphaerella arachidis syn. Cercospora arachidicola (brown leaf spot of peanut). Fungicidal activity was rated on a scale of 100 to 0 (100=no disease growth; 0=well completely covered with mycelium).

Example C2 - Fungicidal activity against Seytoria tritici (leaf mottle)

Fungal conidia from cryogenic storage were directly mixed with nutrient broth (potato dextrose broth, PDB). A solution of test compounds in DMSO was added to a microtiter plate (96-well format) and nutrient broth containing fungal spores was added to it. Test plates were incubated at 24°C and growth inhibition was determined photometrically after 72 h.

The following compound mixtures provided at least 80% control of Septoria tritici at the application rates given in the table, compared to untreated controls under the same conditions that demonstrated extensive disease development.

The following formulations based on mixtures at the concentrations (in ppm) described in Tables C2-3 through C2-5 provided the following disease control in this test against Septoria tritici (leaf mottle). Fungicidal activity was rated on a scale of 100 to 0 (100=no disease growth; 0=well completely covered with mycelium).

Example C3. Fungicidal activity against Seytoria glycines (brown spot)

Fungal conidia collected from culture grown on artificial medium were directly mixed with nutrient broth (PDB potato dextrose broth). A solution of test compounds in DMSO was added to a microtiter plate (96-well format) and nutrient broth containing fungal spores was added to it. Test plates were incubated at 24°C and growth inhibition was determined photometrically after 72 h.

The following compound mixtures provided at least 80% control of Septoria glycines at the rates given in the table, compared to untreated controls under the same conditions that demonstrated extensive disease development.

The following mixture-based formulations at the concentrations (in ppm) described in Tables C3-3 through C3-5 provided the following disease control in this test against Septoria glycines (brown spot). Fungicidal activity was rated on a scale of 100 to 0 (100 = no disease growth; 0 = well completely covered with mycelium).

Example C4. Fungicidal activity against Glomerella lagenarium syn. Colletotrichum lagenarium (anthracnose)

Fungal conidia from cryogenic storage were directly mixed with nutrient broth (potato dextrose broth, PDB). A solution of test compounds in DMSO was added to a microtiter plate (96-well format) and nutrient broth containing fungal spores was added to it. The test plates were incubated at 24°C and growth inhibition was determined photometrically after 72 h at 620 nm.

The following compound mixtures provided at least 80% control of Glomerella lagenarium at the rates given in the table, compared to untreated controls under the same conditions that demonstrated extensive disease development.

The following formulations, based on mixtures at the concentrations (in ppm) described in Tables C4-3 and C4-4, provided the following disease control in this test (Glomerella lagenarium syn. Colletotrichum lagenarium). Fungicidal activity was rated on a scale of 100 to 0 (100 = no disease growth; 0 = well completely covered with mycelium).

Example C5. Fungicidal activity against Corynespora cassiicola (target leaf spot)

Fungal conidia from cryogenic storage were directly mixed with nutrient broth (potato dextrose broth, PDB). A solution of test compounds in DMSO was added to a microtiter plate (96-well format) and nutrient broth containing fungal spores was added to it. Test plates were incubated at 24°C and growth inhibition was determined photometrically after 3-4 days at 620 nm.

The following formulations, based on mixtures at the concentrations (in ppm) described in Tables C4-3 and C4-4, provided the following disease control in this test (Corynespora cassiicola). Fungicidal activity was rated on a scale of 100 to 0 (100 = no disease growth; 0 = well completely covered with mycelium).

Example D. Preventive activity against Phakoysora yachyrhizi on soybean plants

Soybean plants are fully treated with the indicated active ingredients 4 weeks after planting. One day after spraying, leaf discs are cut from the first trifoliate leaf. The test is carried out using five replicates for each application rate. Leaf discs are inoculated with Phakopsora pachyrhizi (Asian soybean rust) one day after treatment. Leaf discs are assessed 11-14 days after inoculation and the activity value is obtained by ratio of the degree of damage in treated plants compared to that in untreated, infested controls. (100 = no disease, no leaf damage, 0 = high infestation, leaf damage is severe). The application rates of the active ingredients used are given in the tables as g active ingredient (a.i.)/ha.

The results are presented in the tables below.

Claims (21)

1. A fungicidal composition containing a mixture of components (A) and (B) as active ingredients, wherein component (A) is: methyl (Z)-2-(5-cyclopentyl-2-methylphenoxy)-3-methoxyprop-2-enoate (compound X.02) or methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxyprop-2-enoate (compound X.04); or its agronomically acceptable salt, And component (B) is a compound selected from the group consisting of bixafen, copper hydroxide, acibenzolar-S-methyl, copper oxychloride, cyproconazole, difenoconazole, epoxiconazole, flutriafol, hexaconazole, metconazole, paclobutrazol, prothioconazole, propiconazole, tebuconazole, fenpropidin, fenpropimorph, fludioxonil, azoxystrobin, dimoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, mancozeb, folpet, chlorothalonil, fluazinam, fluxapyroxad, isopyrazam, sedaxan, benzovindiflupyr, pidiflumetofen, isoflucipram, fluindapyr, inpirfluxam, mefentrifluconazole, aminopyrifene, florillpicoxamide, fenpicoxamide, ipflufenoquine, quinofumelin, fluopyram, methyltetraprol, trinexapac, trinexapac-ethyl, 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]cyclopropanecarboxamide, N,2-dimethoxy-n-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, [(1S,2S)-1-methyl-2-(o-tolyl)propyl]-(2S)-2-[(4-methoxy-3-propanoyloxypyridin-2-carbonyl)amino]propanoate, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, and (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethylpent-3-enamide. 2. The fungicidal composition according to claim 1, wherein component (B) is a compound selected from the group consisting of cyproconazole, difenoconazole, hexaconazole, prothioconazole, propiconazole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, mancozeb, chlorothalonil, fluxapyroxade, benzovindiflupyr, isoflucipram and methyltetraprole. 3. A fungicidal composition according to claim 1 or 2, wherein component (B) is azoxystrobin or trifloxystrobin. 4. A fungicidal composition according to any one of paragraphs 1-3, wherein the weight ratio of component (A) and component (B) is from 100:1 to 1:100. 5. A fungicidal composition according to any one of paragraphs 1-4, wherein the weight ratio of component (A) and component (B) is from 20:1 to 1:40. 6. A fungicidal composition according to any one of paragraphs 1-5, wherein the weight ratio of component (A) and component (B) is from 12:1 to 1:25. 7. A fungicidal composition according to any one of claims 1-6, wherein the weight ratio of component (A) and component (B) is from 5:1 to 1:15. 8. A fungicidal composition according to any one of claims 1-7, wherein the weight ratio of component (A) and component (B) is from 2:1 to 1:5. 9. A fungicidal composition according to any one of claims. 1-8, wherein the composition comprises one or more additional pesticides selected from the group consisting of a fungicide selected from etridiazole, fluazinam, benzovindiflupyr, pydiflumetofen, benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M, dodicin, N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylformamidine, N'-[4-(4,5-dichlorothiazol-2-yloxy)-2,5-dimethylphenyl]-N-ethyl-N-methylformamidine, N'-[4-[[3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl]oxy]-2,5-dimethylphenyl]-N-ethyl-N-methylformamidine, ethrimol, 3'-chloro-2-methoxy-N-[(3RS)-tetrahydro-2-oxofuran-3-yl]acet-2',6'-xylidide, cyprodinil, mepanipyrim, pyrimethanil, dithianon, aureofungin, blasticidin-S, biphenyl, chloroneb, dicloran, hexachlorobenzene, quintozene, teknazen, tolclofos-methyl, metrafenone, 2,6-dichloro-N-(4-trifluoromethylbenzyl)benzamide, fluopicolide, thioximide, flusulfamide, benomyl, carbendazim, carbendazim hydrochloride, chlorphenazole, fuberidazole, thiabendazole, thiophanate-methyl, benthiavalicarb, chlobenthiazone, probenazole, acibenzolar, betoxazine, pyriophenone, acibenzolar-S-methyl, pyribencarb, butylamine, 3-iodo-2-propynyl-n-butylcarbamate, iodocarb, picarbutrazox, polycarbamate, propamocarb, tolprocarb, 3-(difluoromethyl)-N-(7-fluoro-1,1,3,3-tetramethylindan-4-yl)-1-methylpyrazol-4-carboxamide, diclocymet, N-[(5-chloro-2-isopropylphenyl)methyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methylpyrazol-4-carboxamide, N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-[(2-isopropylphenyl)methyl]-1-methylpyrazole-4-carboxamide, carpropamide, chlorothalonil, flumorph, copper oxinate, cymoxanil, fenamacryl, cyazofamide, flutianil, thicyophene, chlozolinate, iprodione, procymidone, vinclozolin, bupirimate, dinoctone, dinopentone, dinobutone, dinocap, meptyldinocap, diphenylamine, fosdiphene, 2,6-dimethyl-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetraone, azithiram, etema, ferbama, mancozeba, maneb, metam, metiram, metiram-zinc, nabam, propineb, thiram, vapam, zineb, ziram, dithioether, isoprothiolane, ethaboxam, fosetyl, fosetyl-aluminum, methyl bromide, methyl iodide, methyl isothiocyanate, cyclafuramide, fenfuram, validamycin, (2RS)-2-bromo-2-(bromomethyl)glutaronitrile, dodine, doguadine, guazatine, iminoctadine, iminoctadine triacetate, 2,4-D, 2,4-DB, kasugamycin, dimethirimol, fenhexamide, hymexazole, hydroxyisoxazole, imazalil, imazalyl sulfate, oxpoconazole, pefurazoate, prochloraz, triflumizole, fenamidone, Bordeaux mixture, calcium polysulfide, copper acetate, copper carbonate, copper hydroxide, copper naphthenate, copper oleate, copper oxychloride, copper oxyquinolate, copper silicate, copper sulfate, copper tallate, copper oxide, sulfur, carbaryl, phthalide, pyrisoxazole, oxathiapiproline, fluorimide, mandipropamide, KSF-1002, benzamorph, dimethomorph, fenpropimorph, tridemorph, dodemorph, diethofencarb, fentin acetate, fentin hydroxide, carboxin, oxycarboxin, drazoxolone, famoxadone, m-phenylphenol, p-phenylphenol, tribromophenol, 2-[2-[(7,8-difluoro-2-methyl-3-quinolyl)oxy]-6-fluorophenyl]propan-2-ol, 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phenyl]propan-2-ol, cyflufenamide, ofuras, oxadixil, flutolanil, mepronil, isofetamide, fenpiclonil, fludioxonil, pencycuron, edifenphos, iprobenfos, pyrazophos, phosphoric acids, tecloftalam, captafol, captan, dithalymphos, triforine, fenpropidin, piperaline, osthole, 1-methylcyclopropene, 4-CPA, chlormequat, clofencet, dichlorprop, dimethipine, endothal, ethephon, flumetralin, forchlorfenuron, gibberellic acid, gibberellins, maleic hydrazide, mepiquat, naphthaleneacetamide, paclobutrazol, prohexadione, prohexadione calcium, thidiazuron, tribufos, trinexapac, uniconazole, α-naphthaleneacetic acid, polyoxin D (polyoxrim), BLAD, chitosan, fenoxanil, folpet, 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichlorophenyl)ethyl]pyrazole-4-carboxamide, bixafen, fluxapyroxad, furametpyr, isopyrazam, penflufen, penthiopyrad, sedaxan, fenpyrazamine, diclomezine, pyrifenox, boscalid, fluopyram, diflumetorim, fenarimol, 5-fluoro-2-(p-tolylmethoxy)pyrimidin-4-amine, ferimzone, dimethaclone, pyroquillone, proquinazid, ethoxyquin, quinoxyfen, 4,4,5-trifluoro-3,3-dimethyl-1-(3-quinolyl)isoquinoline, 4,4-difluoro-3,3-dimethyl-1-(3-quinolyl)isoquinoline, 5-fluoro-3,3,4,4-tetramethyl-1-(3-quinolyl)isoquinoline, 9-fluoro-2,2-dimethyl-5-(3-quinolyl)-3H-1,4-benzoxazepine, tebufloquine, oxolinic acid, quinomethionate, spiroxamine, (E)-N-methyl-2-[2-(2,5-dimethylphenoxymethyl)phenyl]-2-methoxyiminoacetamide, azoxystrobin, cumoxystrobin, dimoxystrobin, enestroburin, pyriotrobin, phenamistrobin, flufenoxystrobin, fluoxastrobin, kresoxim-methyl, mandestrobin, metominostrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyramethostrobin, pyraoxystrobin, trichloropyricarb, trifloxystrobin, amisulbrom, dichlofluanide, tolylfluanide, but-3-ynyl-N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenylmethylene]amino]oxymethyl]-2-pyridyl]carbamate, dazomet, isothianil, tiadinil, thifluzamide, benthiazole, silthiofam, zoxamide, anilazine, 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)propan-2-ol, 2-(1-tert-butyl)-1-(2-chlorophenyl)-3-(1,2,4-triazol-1-yl)-propan-2-ol, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxyethoxy)-3-pyridyl]-N-ethyl-N-methylformamidine, aconazole, bitertanol, bromuconazole, climbazole, cyproconazole, difenoconazole, dimethconazole, diniconazole, diniconazole-M, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole, propiconazole, prothioconazole, mefentrifluconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triazoxide, triticonazole, 2-[[(1R,5S)-5-[(4-fluorophenyl)methyl]-1-hydroxy-2,2-dimethylcyclopentyl]methyl]-4H-1,2,4-triazole-3-thione, 2-[[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl]-4H-1,2,4-triazole-3-thione, amethoctradine, iprovalicarb, valiphenalate, 2-benzyl-4-chlorophenol, allyl alcohol, azaphenidine, benzalkonium chloride, chloropicrin, cresol, daracid, dichlorophene, difenzoquat, dipyrithione, N-(2-p-chlorobenzoylethyl)hexaminium chloride, NNF-0721, octhilinone, oxasulfuron; a plant extract containing tea tree oil Melaleuca alternifolia, propamidine and propionic acid, or an insecticide selected from abamectin, acephate, acetamiprid, amidoflumet, avermectin, azadirachtin, azinphos-methyl, bifenthrin, bifenazate, broflanilide, buprofezin, carbofuran, cartap, chlorantraniliprole, chlorfenapyr, chlorfluazuron, chlorpyrifos, chlorpyrifos-methyl, cromafenozide, clothianidin, cyflumetofen, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, cypermethrin, cyromazine, deltamethrin, diafenthiuron, diazinon, dieldrin, diflubenzuron, dimefluthrin, dimethoate, dinotefuran, diophenolan, emamectin, endosulfan, esfenvalerate, ethiprole, phenothiocarb, fenoxycarb, fenvalerate, fipronil, flonicamid, flubendiamide, flucitrinate, tau-fluvalinate, flufenerim, flufenoxuron, phonofos, halofenoside, hexaflumuron, hydramethylnon, imidacloprid, indoxacarb, isofenphos, lufenuron, malathion, metaflumizone, metaldehyde, methamidophos, methidathione, methomyl, methoprene, methoxychlor, metofluthrin, monocrotophos, methoxyfenozide, nitenpyram, nithiazine, novaluron, noviflumuron, oxamil, parathion, parathion-methyl, permethrin, phorate, fosalone, phosmet, phosphamidon, pirimicarb, profenofos, profluthrin, pymetrozine, pyrafloprol, pyrethrin, pyridalyl, pyrifluquinazone, pyriprol, pyriproxyfen, rotenone, ryanodine, spinetoram, spinosad, spirodiclofen, spiromesifen, spirotetramate, sulprofos, tebufenozide, teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos, thiacloprid, thiamethoxam, thiodicarb, thiosultap sodium, tralomethrin, triazamate, trichlorfon, and triflumuron, or a bactericide selected from streptomycin, or an acaricide selected from amitraz, chlorobenzilate, cyenopyrafen, cyhexatin, dicofol, dienochlor, etoxazole, fenazaquine, fenbutatin oxide, fenpropathrin, fenpyroximate, hexythiazox, propargite, pyridaben and tebufenpyrad, or a biological agent selected from Bacillus thuringiensis, Bacillus thuringiensis delta-endotoxin, baculovirus, a biostimulant containing organic carbon, nutrients and amino acids, and entomopathogenic bacteria, viruses and fungi. 10. A fungicidal composition according to any one of claims 1 to 9, wherein the composition further comprises an agriculturally acceptable carrier and optionally a surfactant and/or formulation aids. 11. A method for monitoring phytopathogenic diseases of useful plants or their propagation material, especially those caused by phytopathogenic fungi, which involves the use of a fungicidal composition according to any of paragraphs 1-10 in relation to useful plants, their growing site or their propagation material. 12. A method for preventing phytopathogenic diseases of useful plants or their propagation material, especially those caused by phytopathogenic fungi, which involves using a fungicidal composition according to any of paragraphs 1-10 in relation to useful plants, their growing site or their propagation material. 13. The method according to claim 11 or 12, wherein components (A) and (B) of the composition are applied sequentially.