EA047972B1 - COMBINATION OF ACTIVE COMPOUNDS AND A FUNGICIDAL COMPOSITION CONTAINING IT - Google Patents

Description

The present invention relates to combinations of active compounds comprising, as compound (A), methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoate, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoic acid or a mixture thereof, as compound (B), isoflucipram and, as compound (C), at least one additional respiratory chain inhibitor in complex I or II. The invention further relates to fungicidal compositions containing such a combination of compounds and the use of combinations of compounds and fungicidal compositions as a biologically active substance for combating phytopathogenic fungi in the protection of agricultural crops and industrial materials, as well as plant growth regulators.

In the text of the present invention, the terms composition and formulation are used as synonyms and refer to mixtures of a combination of compounds according to the invention and at least one agriculturally suitable auxiliary substance.

Methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoate and 2-[2-chloro4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoic acid, their preparation and the fungicidal efficacy of said compounds are known from WO 2019/093522 A1. WO 2019/093522 A1 also discloses compositions comprising at least one of said compounds, and furthermore also combinations of active compounds comprising at least one of said compounds and at least one additional active ingredient, in particular an additional fungicide.

Methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoate, 2-[2-chloro4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoic acid and known combinations of compounds comprising any of these compounds provide excellent plant protection products against diseases caused by fungi. However, there is still a need to even improve these products in order to meet the ever-increasing environmental and economic demands placed on modern plant protection products and formulations. This includes, for example, improving the spectrum of activity, safety profile, selectivity, application rate, residue formation and favorable formulability, as well as developing new formulations to address potential challenges such as resistance.

The present invention provides combinations of active compounds and compositions containing said combinations that at least in some respects meet the said objectives.

Accordingly, the present invention provides combinations of active compounds comprising:

(A) methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoate,

2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoic acid or a mixture thereof;

(B) isoflucipram and (C) at least one additional active compound selected from the group of respiratory chain inhibitors in complex I or II, wherein at least one additional active compound (C) is different from compounds (A) and (B).

The active compound combinations according to the invention comprise, as compound (A), methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoate, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoic acid or a mixture thereof, wherein the compounds may be present in the form of their salt or N-oxide. The salts or N-oxides of the said compounds also have fungicidal properties.

Methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoate is depicted by formula (I-1) and is hereinafter also referred to as compound (I-1) or simply (I-1).

2-[2-Chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoic acid is depicted by formula (I-2) and is hereinafter also designated as compound (I-2) or simply (I-2).

Compound (I-1), compound (I-2) and their mixtures are hereinafter collectively referred to as compound (I) or simply (I).

As is evident from formulas (I-1) and (I-2), compounds (I-1) and (I-2) contain a stereogenic center at the carbon atom bearing a hydroxyl group. Therefore, the compounds can be present in the form of optical isomers, their racemic or scalemic mixtures (the term scalemic means a mixture of enantiomers in different proportions), in all proportions. Compounds (I-1) and (I-2) can be used in the combinations of active compounds according to the present invention in any of the indicated forms, i.e. (I-1) may be present as methyl (2R)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoate, methyl (2R)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3(1,2,4-triazol-1-yl)propanoate, the racemate of methyl (2R)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3(1,2,4-triazol-1-yl)propanoate and methyl (2R)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoate, and any scalemic mixture of methyl (2R)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]2-hydroxy-3-(1,2,4-triazol-1-yl)propanoate and methyl (N)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2hydroxy-3-(1,2,4-triazol-1-yl)propanoate, and (I-2) may be present as (2R)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoic acid, (N)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoic acid, racemate (2R)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoic acid and (2R)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoic acid, and any scalemic mixture of (2R)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoic acid and (2R)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoic acid.

Preferably, the combinations of active compounds according to the invention comprise, as compound (A), compound (I-1).

The combinations of active compounds according to the invention include isoflucipram as compound (B).

Isoflucipram is the common name for N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-pyrazole-4-carboxamide, also designated as N-[(5-chloro-2-isopropylphenyl)methyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methylpyrazole-4-carboxamide, with the CAS registry number: 1255734-28-1. Isoflucipram is also referred to hereinafter as compound (II) or simply (II).

The combinations of active compounds according to the invention additionally comprise at least one compound (C) selected from the respiratory chain inhibitors in complex I or II, wherein at least one additional active compound (C) is different from compounds (A) and (B).

Compound (B) is preferably selected from the following:

respiratory chain inhibitors in complex I or II, selected from the group consisting of (2.001) benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2.004) carboxin, (2.005) fluopyram, (2.006) flutolanil, (2.007) fluxapyroxade, (2.008) furamethpyra, (2.009) isofetamide, (2.010) isopyrazam (anti-epimeric enantiomer 1R,4S,9S), (2.011) isopyrazam (anti-epimeric enantiomer 1S,4R,9R), (2.012) isopyrazam (anti-epimeric racemate 1RS,4SR,9SR), (2.013) isopyrazam (mixture of syn-epimer racemate 1RS,4SR,9RS and anti-epimer racemate 1RS,4SR,9SR), (2.014) isopyrazam (syn-epimer enantiomer 1R,4S,9R), (2.015) isopyrazam (syn-epimer enantiomer 1S, 4R,9S), (2.016) isopyrazam (syn-epimer racemate 1RS,4SR,9RS), (2.017) penflufen, (2.018) penthiopyrad, (2.019) pydiflumetofen, (2.020) pyraziflumid, (2.021) sedaxan, (2.022) 1,3-dimethyl-N-(1,1,3trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazol-4-carboxamide, (2.023) 1,3-dimethyl-K-[ (3C)-1,1,3trimethyl-2,3-dihydro-N-inden-4-yl]-III-pyrazol-4-carboxamide, (2.024) 1,3-damethyl-K-[(38)-1 ,1,3trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazol-4-carboxamide, (2.025) 1-methyl-3-(trifluoromethyl)-N[2'-(trifluoromethyl)biphenyl -2-yl]-III-pyrazol-4-carboxamide, (2.026) 2-fluoro-6-(trifluoromethyl)-N-( 1,1,3-trimethyl-2,3-dihydro-III-inden-4-yl)benzamide, (2.027) inpirfluxam, (2.028) 3-(difluoromethyl)-1methyl-N-(1,1,3-trimethyl-2 ,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide, (2.029) 3 -(difluoromethyl)-1-methyl-N-[(3S)-1,1,3-trimethyl- 2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.030) 3-(difluoromethyl)-H-(7-fluoro-1,1,3-trimethyl-2,3 -dihydro-1H-inden-4-yl)-1-methyl-1H-pyrazole-4-carboxamide (common name: fluindapyr), (2.031) 3-(difluoromethyl)-N-[(3R)-7-fluoro1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl- 1H-pyrazole-4-carboxamide, (2.032) 3-(difluoromethyl)-H-[^)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]- 1-methyl-1H-pyrazole-4-carboxamide, (2.033) 5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}phenyl) ethyl]quinazolin-4amine, (2.034) N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-Spyrazole-4-carboxamide, (2.035) N-(2-tert-butyl-5-methylbenzyl) -N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.036) N(2-tert-butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro -1-methyl-III-pyrazole-4-carboxamide, (2.037) N(5-chloro-2-ethylbenzyl)-N-cyclopropyl-3(difluoromethyl)-5-fluoro-1-methyl-III-pyrazole-4- carboxamic acid, (2.038) isoflucipram, (2.039) N-[(1R,4S)9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-III- pyrazole-4-carboxamide, (2.040) N[(^^)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3(difluoromethyl)-1-methyl- 1H-pyrazole-4-carboxamide, (2.041) N[1-(2,4-dichlorophenyl)-1-methoxypropan-2yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.042 ) No.[2-chloro-6-(trifluoromethyl)benzyl]No.cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.043) No.[3-chloro-2-fluoro6 -(trifluoromethyl)benzyl]-H-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide,

- 2 047972 (2.044) N-[5-chloro-2-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.045) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-[5-methyl-2(trifluoromethyl)benzyl]-1H-pyrazole-4-carboxamide, (2.046) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N(2-fluoro-6-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.047) N-cyclopropyl 3-(difluoromethyl)-5-fluoro-N-(2-isopropyl-5-methylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.048) N-cyclopropyl 3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carbothioamide, (2.049) N-cyclopropyl 3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.050) N-cyclopropyl 3-(difluoromethyl)-5-fluoro-N-(5-fluoro-2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.051) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.052) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.053) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.054) N-cyclopropyl-N-(2-cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.055) N-cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.056) N-cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.057) pyrapropoine, (2.058) N-[rac-(1S,2S)-2-(2,4-dichlorophenyl)cyclobutyl]-2-(trifluoromethyl)nicotinamide, (2.059) N-[(1S,2S)-2-(2,4-dichlorophenyl)cyclobutyl]-2-(trifluoromethyl)nicotinamide and (2.060) cyclobutrifluram.

Compound (C) is more preferably selected from (2.001) benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2.005) fluopyram, (2.007) fluxapyroxad, (2.009) isofetamide, (2.010) isopyrazam (anti-epimer enantiomer 1R,4S,9S), (2.011) isopyrazam (anti-epimer enantiomer 1S,4R,9R), (2.012) isopyrazam (anti-epimer racemate 1RS,4SR,9SR), (2.013) isopyrazam (mixture of syn-epimer racemate 1RS,4SR,9RS and anti-epimer racemate 1RS,4SR,9SR), (2.014) isopyrazam (syn-epimer enantiomer 1R,4S,9R), (2.015) isopyrazam (syn-epimer enantiomer 1S,4R,9S), (2.016) isopyrazam (syn-epimer racemate 1RS,4SR,9RS), (2.017) penflufen, (2.018) penthiopyrad, (2.019) pydiflumetofen, (2.021) sedaxan, (2.027) inpirfluxam, (2.030) fluindapyr, (2.038) isoflucipram and (2.060) cyclobutrifluram.

Compound (C) is even more preferably selected from (2.001) benzovindiflupyr, (2.002) bixafen, (2.005) fluopyram, (2.007) fluxapyroxad, (2.017) penflufen, (2.018) penthiopyrad, (2.019) pydiflumetofen, (2.021) sedaxan, (2.027) inpirfluxam, (2.030) fluindapyr and (2.060) cyclobutrifluram.

Compound (C) is even more preferably selected from (2.002) bixafen, (2.005) fluopyram, (2.007) fluxapyroxad, (2.017) penflufen, (2.019) pidiflumetofen, (2.021) sedaxan, (2.027) inpirfluxam and (2.060) cyclobutrifluram.

Compound (C) is also even more preferably selected from (2.002) bixafen, (2.005) fluopyram, (2.017) penflufen, (2.019) pidiflumetofen and (2.027) inpirfluxam.

Compound (C) is most preferably selected from (2.005) fluopyram, (2.019) pydiflumetofen and (2.060) cyclobutrifluram.

The combinations of compounds according to the invention may comprise one, two or more compounds (C). Preferably, the combinations of compounds according to the invention comprise one or two compounds (C), more preferably only one compound (C).

Preferred combinations of compounds are selected from the group (T1-1) consisting of the following mixtures:

(1-1) + (P) + (2.001), (1-1) + (II) + (2.002), (1-1) + (II) + (2.003), (1-1) + (II ) + (2.004), (I1) + (II) + (2.005), (1-1) + (II) + (2.006), (1-1) + (II) + (2.007), (1-1 ) + (II) + (2.008), (1-1) + (II) + (2.009), (1-1) + (II) + (2.010), (1-1) + (II) + (2.011 ), (1-1) + (II) + (2.012), (1-1) + (II) + (2.013), (1-1) + (II) + (2.014), (1-1) + (II) + (2.015), (1-1) + (II) + (2.016), (1-1) + (II) + (2.017), (1-1) + (II) + (2.018), (1-1) + (II) + (2.019), (1-1) + (II) + (2.020), (1-1) + (II) + (2.021), (1-1) + (II ) + (2.022), (1-1) + (II) + (2.023), (1-1) + (II) + (2.024), (1-1) + (II) + (2.025), (1 -1) + (II) + (2.026), (1-1) + (II) + (2.027), (1-1) + (II) + (2.028), (1-1) + (II) + (2.029), (1-1) + (II) + (2.030), (1-1) + (II) + (2.031), (1-1) + (II) + (2.032), (1-1 ) + (II) + (2.033), (1-1) + (II) + (2.034), (1-1) + (II) + (2.035), (1-1) + (II) + (2.036 ), (1-1) + (II) + (2.037), (1-1) + (II) + (2.039), (1-1) + (II) + (2.040), (1-1) + (II) + (2.041), (1-1) + (II) + (2.042), (1-1) + (II) + (2.043), (1-1) + (II) + (2.044), (1-1) + (II) + (2.045), (1-1) + (II) + (2.046), (1-1) + (II) + (2.047), (1-1) + (II ) + (2.048), (1-1) + (II) + (2.049), (1-1) + (II) + (2.050), (1-1) + (II) + (2.051), (1 -1) + (II) + (2.052), (1-1) + (II) + (2.053), (1-1) + (II) + (2.054), (1-1) + (II) + (2.055), (1-1) + (II) + (2.056), (1-1) + (II) + (2.057), (1-1) + (II) + (2.058), (1-1 ) + (II) + (2.059), (1-1) + (II) + (2.060).

- 3 047972

Preferred combinations of compounds are also selected from the group (T1-2) consisting of the following mixtures:

(1-2) + (P) + (2.001), (1-2) + (II) + (2.002), (1-2) + (II) + (2.003), (1-2) + (II ) + (2.004), (I2) + (II) + (2.005), (1-2) + (II) + (2.006), (1-2) + (II) + (2.007), (1-2 ) + (II) + (2.008), (1-2) + (II) + (2.009), (1-2) + (II) + (2.010), (1-2) + (II) + (2.011 ), (1-2) + (II) + (2.012), (1-2) + (II) + (2.013), (1-2) + (II) + (2.014), (1-2) + (II) + (2.015), (1-2) + (II) + (2.016), (1-2) + (II) + (2.017), (1-2) + (II) + (2.018), (1-2) + (II) + (2.019), (1-2) + (II) + (2.020), (1-2) + (II) + (2.021), (1-2) + (II ) + (2.022), (1-2) + (II) + (2.023), (1-2) + (II) + (2.024), (1-2) + (II)+ (2.025), (1 -2) + (II) + (2.026), (1-2) + (II) + (2.027), (1-2) + (II) + (2.028), (1-2) + (II)+ (2.029), (1-2) + (II) + (2.030), (1-2) + (II) + (2.031), (1-2) + (II) + (2.032), (1-2 ) + (II)+ (2.033), (1-2) + (II) + (2.034), (1-2) + (II) + (2.035), (1-2) + (II) + (2.036 ), (1-2) + (II)+ (2.037), (1-2) + (II) + (2.039), (1-2) + (II) + (2.040), (1-2) + (II) + (2.041), (1-2) + (II)+ (2.042), (1-2) + (II) + (2.043), (1-2) + (II) + (2.044), (1-2) + (II) + (2.045), (1-2) + (II)+ (2.046), (1-2) + (II) + (2.047), (1-2) + (II ) + (2.048), (1-2) + (II) + (2.049), (1-2) + (II)+ (2.050), (1-2) + (II) + (2.051), (1 -2) + (II) + (2.052), (1-2) + (II) + (2.053), (1-2) + (II)+ (2.054), (1-2) + (II) + (2.055), (1-2) + (II) + (2.056), (1-2) + (II) + (2.057), (1-2) + (II)+ (2.058), (1-2 ) + (II) + (2.059), (1-2) + (II) + (2.060).

Preferred combinations of compounds are also selected from the group (T1-3) consisting of the following mixtures:

(1-1) + (1-2) + (II) + (2.001), (1-1) + (1-2) + (II) + (2.002), (1-1) + (1-2 ) + (II) + (2.003), (I1) + (1-2) + (II) + (2.004), (1-1) + (1-2) + (II) + (2.005), (1 -1) + (1-2) + (II) + (2.006), (1-1) + (1-2) + (P) + (2.007), (1-1) + (1-2) + (II) + (2.008), (1-1) + (1-2) + (II) + (2.009), (1-1) + (I2) + (II) + (2.010), (1-1 ) + (1-2) + (II) + (2.011), (1-1) + (1-2) + (II) + (2.012), (1-1) + (1-2) + (II) + (2.013), (1-1) + (1-2) + (II) + (2.014), (1-1) + (1-2) + (II) + (2.015), (1-1) + (1-2) + (II) + (2.016), (1-1) + (1-2) + (P) + (2.017), (1-1) + (1-2) + (II) + (2.018), (1-1) + (1-2) + (II) + (2.019), (1-1) + (1-2) + (II) + (2.020), (1-1) + (1-2) + (II) + (2.021), (1-1) + (1-2) + (II) + (2.022), (1-1) + (1-2) + (II) + (2.023), (1-1) + (1-2) + (II) + (2.024), (1-1) + (1-2) + (II) + (2.025), (1-1) + (1-2) + (II) + (2.026), (1-1) + (1-2) + (II) + (2.027), (1-1) + (1-2) + (II) + (2.028), (1-1) + (1-2) + (II) + (2.029), (1-1) + (1-2) + (II) + (2.030), (1-1) + (1-2) + (II) + (2.031), (1-1) + (1-2) + (II) + (2.032), (1-1) + (1-2) + (II) + (2.033), (1-1) + (1-2) + (II) + (2.034), (1-1) + (1-2) + (II) + (2.035), (1-1) + (1-2) + (II) + (2.036), (1-1) + (1-2) + (II) + (2.037), (1-1) + (1-2) + (II) + (2.039), (1-1) + (1-2) + (II) + (2.040), (1-1) + (1-2) + (II) + (2.041), (1-1) + (1-2) + (II) + (2.042), (1-1) + (1-2) + (II) + (2.043), (1-1) + (1-2) + (II) + (2.044), (1-1) + (1-2) + (II) + (2.045), (1-1) + (1-2) + (II) + (2.046), (1-1) + (1-2) + (II) + (2.047), (1-1) + (1-2) + (II) + (2.048), (1-1) + (1-2) + (II) + (2.049), (1-1) + (1-2) + (II) + (2.050), (1-1) + (1-2) + (II) + (2.051), (1-1) + (1-2) + (II) + (2.052), (1-1) + (1-2) + (II) + (2.053), (1-1) + (1-2) + (II) + (2.054), (1-1) + (1-2) + (II) + (2.055), (1-1) + (1-2) + (II) + (2.056), (1-1) + (1-2) + (II) + (2.057), (1-1) + (1-2) + (II) + (2.058), (1-1) + (1-2) + (II) + (2.059), (1-1) + (1-2) + (II) + (2.060).

In the combinations according to the invention containing a mixture of (I-1) and (I-2), and in particular in the mixtures from group (T1-3), the compounds (I-1) and (I-2) can be present in a wide range of effective weight ratios of (I-1):(I-2), for example in the range from 100,000:1 to 1:100, preferably in a weight ratio of 100:1-1:100, more preferably in a weight ratio of 50:1-1:50, most preferably in a weight ratio of 20:1-1:20. Additional ratios (I-1):(I-2) which may be used according to the present invention with increasing preference in the order stated are: 95:1-1:95, 90:1-1:90, 85:1-1:85, 80:1-1:80, 75:1-1:75, 70:1-1:70, 65:1-1:65, 60:1-1:60, 55:1-1:55, 45:1-1:45, 40:1-1:40, 35:1-1:35, 30:1-1:30, 25:1-1:25, 15:1-1:15, 10:1-1:10, 5:1-1:5, 4:1-1:4, 3:1-1:3, 2:1-1:2.

Additional ratios of (I-1):(I-2) that can be used according to the present invention are: 95:1-1:1, 90:1-1:1, 85:1-1:1, 80:1-1:1, 75:1-1:1, 70:1-1:1, 65:1-1:1, 60:1-1:1, 55:1-1:1, 45:1-1:1, 40:1-1:1, 35:1-1:1, 30:1-1:1, 25:1-1:1, 15:1-1:1, 10:1-1:1, 5:1-1:1, 4:1-1:1, 3:1-1:1, 2:1-1:1.

Additional ratios (I-1):(I-2) that can be used according to the present invention are: 1:1-1:95, 1:1-1:90, 1:1-1:85, 1:1-1:80, 1:1-1:75, 1:1-1:70, 1:1-1:65, 1:1-1:60,

- 4 047972

1:1-1:55, 1:1-1:45, 1:1-1:40, 1:1-1:35, 1:1-1:30, 1:1-1:25, 1: 1-1:15, 1:1-1:10, 1:1-1:5, 1:1-1:4, 1:1-1:3, 1:1-1:2.

More preferred combinations of compounds are selected from the group (T1-1 A) consisting of the following mixtures:

(1-1) + (P) + (2.001), (1-1) + (II) + (2.002), (1-1) + (II) + (2.003), (1-1) + (II ) + (2.005), (I-

1) + (II) + (2.007), (1-1) + (II) + (2.009), (1-1) + (II) + (2.010), (1-1) + (II) + ( 2.011), (1-1) + (II) + (2.012), (1-1) + (II) + (2.013), (1-1) + (II) + (2.014), (1-1) + (II) + (2.015), (1-1) + (II) + (2.016), (1-1) + (II) + (2.017), (1-1) + (II) + (2.018) , (1-1) + (II) + (2.019), (1-1) + (II) + (2.021), (1-1) + (II) + (2.027), (1-1) + (II) + (2.030), (1-1) + (II) + (2.060).

More preferred combinations of compounds are also selected from the group (T1-2A) consisting of the following mixtures:

(1-2) + (P) + (2.001), (1-2) + (II) + (2.002), (1-2) + (II) + (2.003), (1-2) + (II ) + (2.005), (I-

2) + (II) + (2.007), (1-2) + (II) + (2.009), (1-2) + (II) + (2.010), (1-2) + (II) + ( 2.011), (1-2) + (II) + (2.012), (1-2) + (II) + (2.013), (1-2) + (II) + (2.014), (1-2) + (II) + (2.015), (1-2) + (II) + (2.016), (1-2) + (II) + (2.017), (1-2) + (II) + (2.018) , (1-2) + (II) + (2.019), (1-2) + (II) + (2.021), (1-2) + (II) + (2.027), (1-2) + (II) + (2.030), (1-2) + (II) + (2.060).

Even more preferred combinations of compounds are selected from the group (T1-1B) consisting of the following mixtures:

(1-1) + (II) + (2.001), (1-1) + (II) + (2.002), (1-1) + (II) + (2.005), (1-1) + (II ) + (2.007), (I-

1) + (II) + (2.017), (1-1) + (II) + (2.018), (1-1) + (II) + (2.019), (1-1) + (II) + ( 2.021), (1-1) + (II) + (2.027), (1-1) + (II) + (2.030), (1-1) + (II) + (2.060).

Even more preferred combinations of compounds are also selected from the group (T1-2B) consisting of the following mixtures:

(1-2) + (II) + (2.001), (1-2) + (II) + (2.002), (1-2) + (II) + (2.005), (1-2) + (II ) + (2.007), (I-

2) + (II) + (2.017), (1-2) + (II) + (2.018), (1-2) + (II) + (2.019), (1-2) + (II) + ( 2.021), (1-2) + (II) + (2.027), (1-2) + (II) + (2.030), (1-2) + (II) + (2.060).

Even more preferred combinations of compounds are selected from the group (T1-1C) consisting of the following combinations:

(1-1) + (II) + (2.002), (1-1) + (II) + (2.005), (1-1) + (II) + (2.017), (1-1) + (II ) + (2.019), (I-

1) + (II) + (2.027).

Even more preferred combinations of compounds are also selected from the group (T1-2C) consisting of the following combinations:

(1-2) + (P) + (2.002), (1-2) + (II) + (2.005), (1-2) + (II) + (2.017), (1-2) + (II ) + (2.019), (I-

2) + (II) + (2.027).

Even more preferred combinations of compounds are selected from the group (T1-1D) consisting of the following combinations:

(1-1) + (II) + (2.005), (1-1) + (II) + (2.019), (1-1) + (II) + (2.060).

Even more preferred combinations of compounds are also selected from the group (T1-2C) consisting of the following combinations:

(1-2) + (II) + (2.005), (1-2) + (II) + (2.019), (1-2) + (II) + (2.060).

Most preferably, the combinations of compounds are selected from the group (Τι-ID).

In the combinations according to the invention, the compounds (A) and (B) can be present in a wide range of effective weight ratios of A:B, for example in the range of 1000:1-1:1000, 750:1-1:750, 500:1-1:500, 400:1-1:400, 300:1-1:300, 250:1-1:250, 200:1-1:200, 150:1-1:150, 100:1-1:100, preferably in a weight ratio of 50:1-1:50, most preferably in a weight ratio of 20:1-1:20.

Additional A:B ratios that may be used according to the present invention with increasing preference in the order given are: 95:1-1:95, 90:1-1:90, 85:11:85, 80:1-1:80, 75:1-1:75, 70:1-1:70, 65:1-1:65, 60:1-1:60, 55:1-1:55, 45:1-1:45, 40:1-1:40, 35:1-1:35, 30:11:30, 25:1-1:25, 15:1-1:15, 10:1-1:10, 5:1-1:5, 4:1-1:4, 3:1-1:3, 2:1-1:2.

Additional A:B ratios that can be used according to the present invention are: 1000:1-1:1, 750:1-1:1, 500:1-1:1, 250:1-1:1, 95:1-1:1, 90:1-1:1, 85:1-1:1, 80:1-1:1, 75:1-1:1, 70:1-1:1, 65:1-1:1, 60:1-1:1, 55:1-1:1, 45:1-1:1, 40:1-1:1, 35:1-1:1, 30:1-1:1, 25:1-1:1, 15:1-1:1, 10:11:1, 5:1-1:1, 4:1-1:1, 3:1-1:1,2:1-1:1.

Additional A:B ratios that can be used according to the present invention are: 1:1-1:1000, 1:1-1:750, 1:1-1:500, 1:1-1:250, 1:1-1:95, 1:1-1:90, 1:1-1:85, 1:1-1:80, 1:1-1:75, 1:1-1:70, 1:1-1:65, 1:1-1:60, 1:1-1:55, 1:1-1:45, 1:1-1:40, 1:1-1:35, 1:1-1:30, 1:1-1:25, 1:1-1:15, 1:11:10, 1:1-1:5, 1:1-1:4, 1:1-1:3, 1:1-1:2.

In the combinations according to the invention, compounds (A) and (C) may be present in a wide range

- 5 047972 in the range of the effective mass ratio A:C, for example in the range of 1000:1-1:1000, 750:1-1:750, 500:1-1:500, 400:1-1:400, 300:1-1:300, 250:1-1:250, 200:1-1:200, 150:1-1:150, 100:1-1:100, preferably in a mass ratio of 50:1-1:50, most preferably in a mass ratio of 20:1-1:20.

Additional A:C ratios which may be used according to the present invention with increasing preference in the order stated are: 95:1-1:95, 90:1-1:90, 85:11:85, 80:1-1:80, 75:1-1:75, 70:1-1:70, 65:1-1:65, 60:1-1:60, 55:1-1:55, 45:1-1:45, 40:1-1:40, 35:1-1:35, 30:11:30, 25:1-1:25, 15:1-1:15, 10:1-1:10, 5:1-1:5, 4:1-1:4, 3:1-1:3, 2:1-1:2.

Additional A:C ratios that can be used according to the present invention are: 1000:1-1:1, 750:1-1:1, 500:1-1:1, 250:1-1:1, 95:1-1:1, 90:1-1:1, 85:1-1:1, 80:1-1:1, 75:1-1:1, 70:1-1:1, 65:1-1:1, 60:1-1:1, 55:1-1:1, 45:1-1:1, 40:1-1:1, 35:1-1:1, 30:1-1:1, 25:1-1:1, 15:1-1:1, 10:11:1, 5:1-1:1, 4:1-1:1, 3:1-1:1,2:1-1:1.

Additional A:C ratios that can be used according to the present invention are: 1:1-1:1000, 1:1-1:750, 1:1-1:500, 1:1-1:250, 1:1-1:95, 1:1-1:90, 1:1-1:85, 1:1-1:80, 1:1-1:75, 1:1-1:70, 1:1-1:65, 1:1-1:60, 1:1-1:55, 1:1-1:45, 1:1-1:40, 1:1-1:35, 1:1-1:30, 1:1-1:25, 1:1-1:15, 1:11:10, 1:1-1:5, 1:1-1:4, 1:1-1:3, 1:1-1:2.

In the combinations according to the invention, the compounds (B) and (C) can also be present in a wide range of effective mass ratios B:C. The corresponding mass ratio is automatically determined on the basis of the selected mass ratios A:B and A:C.

If more than one, e.g. 2 or 3, compounds (C) are present, the mass ratios refer to the total amount of compound (C), i.e. to the sum of the amounts of each compound (C) present in the combination. The same applies mutatis mutandis to situations where two compounds (A) are present, i.e. a mixture of (I-1) and (I-2).

Isomers.

As already indicated above, compounds (I-1) and (I-2) may be present in the form of different stereoisomers. Depending on the properties of the substituents of compounds (B) and (C), as well as compounds (B) and (C) may be present in the combinations of compounds according to the invention in the form of different stereoisomers. Such stereoisomers may be, for example, enantiomers, diastereomers, atropisomers or geometric isomers. Accordingly, the invention relates both to pure isomers and to any mixtures of these isomers. In cases where a compound may be present in two or more tautomeric forms in equilibrium, if one tautomeric form of the compound is mentioned in the text, then such mention includes all tautomeric forms. Where a compound may be present in isomeric and/or tautomeric forms, such compound when referred to throughout this document also includes, where appropriate, the corresponding isomeric and/or tautomeric forms or mixtures thereof, even if not specifically mentioned.

Salts/N-oxides.

Depending on the properties of the substituents, the compounds present in the combinations of compounds according to the invention may be present in the form of a free compound and/or their solvate and/or an agrochemically active salt and/or an N-oxide.

Agrochemically active salts include acid addition salts of inorganic and organic acids, as well as salts of common bases. Examples of inorganic acids are hydrohalic acids such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide, sulfuric acid, orthophosphoric acid and nitric acid, and acid salts such as sodium bisulfate and potassium bisulfate. Suitable organic acids include, for example, formic acid, carboxylic acid and alkanoic acids such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid, as well as glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, saturated or mono- or di-unsaturated fatty acids with 6 to 20 carbon atoms, alkyl sulfuric acid monoesters, alkyl sulfonic acids (sulfonic acids with straight-chain or branched alkyl radicals with 1 to 20 carbon atoms), arylsulfonic acids or aryl disulfonic acids (aromatic radicals such as phenyl and naphthyl that carry one or two sulfonic acid groups), alkyl phosphonic acids (phosphonic acids with straight-chain or branched alkyl radicals with 1-20 carbon atoms), arylphosphonic acids or aryl diphosphonic acids (aromatic radicals such as phenyl and naphthyl which carry one or two phosphonic acid radicals), where the alkyl and aryl radicals may carry additional substituents, for example p-toluenesulfonic acid, salicylic acid, p-aminosalicylic acid, 2-phenoxybenzoic acid, 2-acetoxybenzoic acid.

Solvates of the compounds present in the combinations of compounds of the invention, or their salts, are stoichiometric compositions of the compounds with solvents.

N-Oxides of the compounds present in the combinations of compounds of the invention or intermediates thereof can be prepared by simple methods using conventional processes, for example by _{N-oxidation with hydrogen peroxide (H2O2 )} , peracids such as persulfuric acid, or percarboxylic acids such as meta-chloroperoxybenzoic acid or peroxomono

- 6 047972 sulfuric acid (Caro's acid).

For example, the corresponding N-oxides can be prepared starting from the corresponding compounds using conventional oxidation methods, for example by treating these compounds with an organic peracid such as metachloroperbenzoic acid (e.g. WO 2003/64572 A or J. Med. Chem. 38(11), 1892-1903, 1995); or with inorganic oxidizing agents such as hydrogen peroxide (e.g. J. Heterocyc. Chem. 18(7), 1305-1308, 1981) or oxone (e.g. J. Am. Chem. Soc. 123(25), 5962-5973, 2001). The oxidation can yield pure moho-N-oxides or a mixture of different N-oxides, which can be separated by conventional methods such as chromatography.

Crystalline form.

The compounds present in the inventive compound combinations of the present invention may exist in various crystalline and/or amorphous forms. Crystalline forms include unsolvated crystalline forms, solvates, and hydrates.

Dosage forms.

The present invention also relates to compositions for combating unwanted microorganisms comprising a combination of compounds according to the invention. The compositions can be used to treat the microorganisms themselves and/or their habitat.

The composition comprises one combination of compounds according to the invention and at least an agriculturally suitable auxiliary substance, such as a carrier(s) and/or a surfactant(s).

A carrier is a solid or liquid, natural or synthetic, organic or inorganic substance, which is usually inert. Typically, a carrier enhances the efficiency of application of the active compounds, for example, to plants, plant parts or seeds. Examples of suitable solid carriers include, but are not limited to, ammonium salts, natural rock powder such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite and diatomaceous earth, and synthetic rock powder such as finely divided silica, alumina and silicates. Examples of commonly used solid carriers for producing granules include, but are not limited to, crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granulates from inorganic and organic flours and granulates from organic material such as paper, sawdust, coconut shells, corn cobs and tobacco stalks. Examples of suitable liquid carriers include, but are not limited to, water, organic solvents and combinations thereof. Examples of suitable solvents include polar and non-polar organic chemical liquids, for example from the classes of aromatic and non-aromatic hydrocarbons (such as cyclohexane, paraffins, alkylbenzenes, xylene, toluene, alkylnaphthalenes, chlorinated aromatic compounds or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride), alcohols and polyols (which may optionally also be substituted, etherified and/or esterified), ketones (such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone), esters (including fats and oils) and (poly)esters, unsubstituted and substituted amines, amides (such as dimethylformamide), lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethyl sulfoxide). The carrier may also be a liquefied gas diluent, i.e. a liquid which is in a gaseous state at ordinary temperature and ordinary pressure, for example, aerosol propellants such as halogenated hydrocarbons, butane, propane, nitrogen and carbon dioxide. The amount of carrier is typically in the range of 1-99.99%, preferably 5-99.9%, more preferably 10-99.5%, most preferably 20-99% by weight of the composition.

The surfactant may be an ionic (cationic or anionic) or nonionic surfactant, such as ionic or nonionic emulsifier(s), foaming agent(s), dispersant(s), wetting agent(s), and any mixtures thereof. Examples of such suitable surfactants include, but are not limited to, salts of polyacrylic acid, salts of lignosulfonic acid, salts of phenolsulfonic or naphthalenesulfonic acid, polycondensates of ethylene and/or propylene oxide with fatty alcohols or with fatty acids or with fatty amines (polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, such as alkylaryl polyglycol ethers), substituted phenols (preferably alkylphenols or arylphenols), salts of sulfosuccinic acid esters, taurine derivatives (preferably alkyl taurates), phosphoric acid esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols, derivatives of compounds containing sulfates, sulfonates and phosphates (e.g. alkyl sulfonates, alkyl sulfates, arylsulfonates) and protein hydrolysates, lignosulfite liquor and methylcellulose. A surfactant is typically used when the compound of the combination of compounds of the invention and/or the carrier are insoluble in water but are applied using water. If present, the amount of surfactants is typically 5-40% by weight of the total weight of the composition.

Other examples of suitable excipients include water-repellent agents

- 7 047972 you, siccatives, binders (adhesives, tackifiers, fixatives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latex dispersions such as gum arabic, polyvinyl alcohol and polyvinyl acetate, natural phospholipids such as cephalins and lecithins and the synthetic phospholipids polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose), thickeners, stabilizers (e.g. cold stabilizers, preservatives, antioxidants, light stabilizers or other agents improving chemical and/or physical stability), dyes or pigments (such as inorganic pigments such as iron oxide, titanium oxide and Prussian blue; organic dyes such as alizarin, azo and phthalocyanine metallic dyes), antifoams (e.g. silicone antifoams and magnesium stearate), preservatives (e.g. dichlorphen and benzyl alcohol semiformal), secondary thickeners (cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica), adhesives, gibberellins and processing aids, mineral and vegetable oils, flavourings, waxes, nutrients (including trace elements such as iron, manganese, boron, copper, cobalt, molybdenum and zinc salts), protective colloids, thixotropic agents, penetrants, sequestrants and complexing agents.

The choice of auxiliary substances depends on the intended method of use of the combination of compounds according to the invention and/or on the physical properties. In addition, auxiliary substances can be selected in such a way as to impart certain properties (technical, physical and/or biological properties) to the formulations/compositions or forms for use obtained from such compounds. By choosing appropriate auxiliary substances, it is possible to prepare compositions depending on specific needs.

The composition may be in any conventional form, such as a solution (e.g. aqueous solution), emulsion, wettable powder, aqueous or oil-based suspension, powder, dust, paste, soluble powder, soluble granules, granules for broadcast application, suspoemulsion concentrates, natural or synthetic products impregnated with a combination of compounds according to the invention, fertilizers, as well as microencapsulations in a polymeric substance. The combination of compounds according to the invention may be in the form of a suspension, emulsion or solution.

The formulations can be prepared by known methods, for example by mixing the active ingredients with at least one excipient.

The composition may be provided to the end user as a ready-to-use preparation, i.e. the compositions may be applied directly to the plants or seeds using a suitable device such as a sprayer or atomizer. Alternatively, the compositions may be provided to the end user as concentrates that must be diluted, preferably with water, before use.

The formulations typically contain from 0.01 to 99% by weight, from 0.05 to 98% by weight, preferably from 0.1 to 95% by weight, more preferably from 0.5 to 90%, most preferably from 1 to 80% by weight of the combination of compounds of the present invention. If the composition contains two or more active ingredients, the ranges given refer to the total amount of the combination of compounds of the present invention.

The above-described formulations can be used to combat unwanted microorganisms by applying them to the microorganisms and/or their area of distribution.

In one particular embodiment of the invention, the combination of compounds is provided in a sprayable form, allowing its application by spraying. In this embodiment, the combination of compounds according to the invention is provided in the form of a composition/formulation comprising the active ingredients and at least one suitable liquid carrier.

Suitable liquid carriers are preferably selected from water, organic solvents and combinations thereof. More preferably, the liquid carrier is water or a mixture of water and an organic solvent.

Preferred suitable organic solvents are those already described above.

The amount of liquid carrier is typically in the range of 1-99.99%, preferably 5-99.9%, more preferably 10-99.5%, most preferably 20-99% by weight of the composition.

Preferably, the sprayable composition further comprises at least one surfactant. Suitable surfactants are described above. This may also include at least one additional auxiliary element, as noted above.

Preferably, the sprayable composition is presented in the form of an emulsifiable concentrate or a suspension concentrate, more preferably an emulsifiable concentrate containing active ingredients in a total amount of from 20 to 400 g/l, preferably from 40 to 200 g/l, or a suspension concentrate containing active ingredients in a total amount of from 50 to 500 g/l, preferably from 100 to 400 g/l.

- 8 047972

The preparation of said concentrates is well known to those skilled in the art. For example, emulsifiable concentrates (EC) can be prepared by dissolving the desired amount of active ingredients, for example, from 20 to 400 g per 1 l of concentrate and from 50 to 100 g per 1 l of concentrate of at least one surfactant in a water-insoluble organic solvent, for example, in an aromatic hydrocarbon, or a water-soluble organic solvent, for example, N-methyl-2-pyrrolidone (NMP), dimethyl sulfoxide (DMSO), γ-butyrolactone. Suspension concentrates (SC) can be obtained by mixing the desired amount of active ingredients, for example, from 50 to 500 g per 1 l of concentrate, from 20 to 100 g per 1 l of concentrate of at least one surfactant and from 1 to 20 g per 1 l of concentrate of at least one binder and/or secondary thickener and suspending this mixture in water.

Preferably, before applying said concentrates to a plant or part thereof, the concentrate is diluted with water. More preferably, the emulsifiable concentrate or suspension concentrate is mixed with water in such an amount as to obtain a total concentration of active ingredients in the resulting mixture of 0.1 to 5, preferably 0.2 to 2, more preferably 0.25 to 1 g/l.

Additional active ingredients.

The combinations of the compounds of the present invention can be used alone or in the form of compositions/preparations and can be mixed with additional known active ingredients, such as bactericides, acaricides, nematicides or insecticides, in order to thereby broaden, for example, the spectrum of activity or prevent the development of resistance.

Suitable substances for use in the mixture include, for example, insecticides, acaricides, nematicides, and bactericides (see also Pesticide Handbook, 14th ed.).

Mixtures with other known active ingredients such as herbicides, or with fertilizers or growth regulators, safeners and/or signal chemicals are also possible.

Examples of biological control agents that can be used in combination with the compound combinations of the invention include the following:

(A) antibacterial agents selected from the group:

(A1) bacteria such as (A1.1) Bacillus subtilis, in particular strain QST713/AQ713 (available as SERENADE OPTI or SERENADE ASO from Bayer CropScience LP, USA, having accession number NRRL B21661 and described in US Patent No. 6,060,051);

(A1.2) Bacillus amyloliquefaciens, in particular strain D747 (available as Double Nickel™ from Certis, USA, having accession number FERM BP-8234 and described in US Patent No. 7,094,592);

(A1.3) Bacilluspumilus, in particular strain BUF-33 (having accession number NRRL 50185);

(A1.4) Bacillus subtilis var. amyloliquefaciens strain FZB24 (available as Taegro® from Novozymes, USA); (A1.5) Paenibacillus sp. strain, having NRRL accession number B-50972 or NRRL accession number B-67129 and described in International Patent Publication No. WO 2016/154297; and (A2) fungi, such as (A2.1) Aureobasidium pullulans, in particular blastospores of strain DSM14940;

(A2.2) blastospores of Aureobasidium pullulans strain DSM 14941; (A2.3) Aureobasidium pullulans, in particular mixtures of blastospores of strains DSM14940 and DSM14941;

(B) biological fungicides selected from the group:

(B1) bacteria, such as (B1.1) Bacillus subtilis, in particular strain QST713/AQ713 (available as SERENADE OPTI or SERENADE ASO from Bayer CropScience LP, USA, having accession number NRRL B21661 and described in US Patent No. 6,060,051);

(B1.2) Bacillus pumilus, in particular strain QST2808 (available as SONATA® from Bayer CropScience LP, USA, having accession number NRRL B-30087 and described in US Patent No. 6,245,551);

(B1.3) Bacillus pumilus, in particular strain GB34 (available as Yield Shield® from Bayer AG, Germany);

(B1.4) Bacillus pumilus, in particular strain BU F-33 (having accession number NRRL 50185);

(B1.5) Bacillus amyloliquefaciens, in particular strain D747 (available as Double Nickel™ from Certis, USA, having accession number FERM BP-8234 and described in US Patent No. 7,094,592);

(B1.6) Bacillus subtilis Y1336 (available as BIOBAC® WP from Bion-Tech, Taiwan, registered as a biological fungicide in Taiwan under registration numbers 4764, 5454, 5096 and 5277);

(B1.7) Bacillus amyloliquefaciens strain MBI 600 (available as SUBTILEX from BASF, Sweden);

(B1.8) Bacillus subtilis strain GB03 (available as Kodiak® from Bayer AG, Germany);

(B1.9) Bacillus subtilis var. amyloliquefaciens strain FZB24 (available from Novozymes Biologicals

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Inc., of Salem, Virginia, or Syngenta Crop Protection, LLC, Greensboro, North Carolina, as TAEGRO® or TAEGRO® ECO fungicide (EPA Registration No. 70127-5);

(B1.10) Bacillus mycoides, isolate J (available as BmJ TGAI or WG from Certis, USA);

(B1.11) Bacillus licheniformis, in particular strain SB3086 (available as EcoGuard™ Biofungicide and Green Releaf from Novozymes);

(B1.12) Paenibacillus sp. strain, having NRRL accession number B-50972 or NRRL accession number B-67129 and described in International Patent Publication No. WO 2016/154297.

In some embodiments, the biological control agent is a strain of Bacillus subtilis or Bacillus amyloliquefaciens that produces a fengycin- or plipastatin-type compound, an iturin-type compound, and/or a surfactin-type compound. For more information, see the following review article: Ongena, M., et al., Bacillus Lipopeptides: Versatile Weapons for Plant Disease Biocontrol, Trends in Microbiology, Vol. 16, No. 3, March 2008, pp. 115-125. Bacillus strains capable of producing lipopeptides include Bacillus subtilis strain QST713 (available as SERENADE OPTI or SERENADE ASO from Bayer CropScience LP, USA, having accession number NRRL B21661 and described in U.S. Patent No. 6,060,051), Bacillus amyloliquefaciens strain D747 (available as Double Nickel™ from Certis, USA, having accession number FERM BP-8234 and described in U.S. Patent No. 7,094,592); Bacillus subtilis MBI600 (available as SUBTILEX® from Becker Underwood, USA EPA Reg. No. 71840-8); Bacillus subtilis Y1336 (available as BIOBAC® WP from Bion-Tech, Taiwan, registered as a biological fungicide in Taiwan under registration numbers 4764, 5454, 5096 and 5277); Bacillus amyloliquefaciens, in particular strain FZB42 (available as RHTZOVITAL® from ABiTEP, Germany); and Bacillus subtilis var. amyloliquefaciens FZB24 (available from Novozymes Biologicals Inc., Salem, VA, or from Syngenta Crop Protection, LLC, Greensboro, NC, as TAEGRO® or TAEGRO® ECO fungicide (EPA registration number 70127-5); and (B2) fungi, such as:

(B2.1) Coniothyrium minitans, in particular strain CON/M/91-8 (accession number DSM-9660; e.g. Contans® from Bayer);

(B2.2) Metschnikowia fructicola, in particular strain NRRL Y-30752 (e.g. Shemer®);

(B2.3) Microsphaeropsis ochracea (e.g. Microx® by Prophyta);

(B2.5) Trichoderma spp., including Trichoderma atroviride, strain SCI, described in International Application No. PCT/IT2008/000196);

(B2.6) Trichoderma harzianum rifai, strain KRL-AG2 (also known as strain T-22, ATCC 208479, e.g. PLANTSHIELD T-22G, Rootshield® and TurfShield from BioWorks, USA);

(B2.14) Gliocladium roseum, strain 321U, produced by W.F. Stoneman Company LLC;

(B2.35) Talaromyces flavus, strain V117b;

(B2.36) Trichoderma asperellum, strain ICC 012 produced by Isagro;

(B2.37) Trichoderma asperellum strain SKT-1 (e.g. ECO-HOPE® by Kumiai Chemical Industry);

(B2.38) Trichoderma atroviride, strain CNCM 1-1237 (e.g. Esquive® WP manufactured by Agrauxine, France);

(B2.39) Trichoderma atroviride, strain No. V08/002387;

(B2.40) Trichoderma atroviride, strain NMI No. V08/002388;

(B2.41) Trichoderma atroviride, strain NMI No. V08/002389;

(B2.42) Trichoderma atroviride, strain NMI No. V08/002390;

(B2.43) Trichoderma atroviride, strain LC52 (e.g. Tenet from Agrimm Technologies Limited);

(B2.44) Trichoderma atroviride, strain ATCC 20476 (IMI206040);

(B2.45) Trichoderma atroviride, strain T11 (1MB52941/CECT20498);

(B2.46) Trichoderma harmatum;

(B2.47) Trichoderma harzianum;

(B2.48) Trichoderma harzianum rifai T39 (e.g. Trichodex® manufactured by Makhteshim, USA);

(B2.49) Trichoderma harzianum, in particular strain KD (e.g. Trichoplus from Biological Control Products, SA (purchased by Becker Underwood));

(B2.50) Trichoderma harzianum, strain ITEM 908 (e.g. Trianum-P by Koppert);

(B2.51) Trichoderma harzianum, strain TH35 (e.g. Root-Pro by

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Mycontrol);

(B2.52) Trichoderma virens (also known as Gliocladium virens), in particular strain GL-21 (e.g. SoilGard 12G by Certis, USA);

(B2.53) Trichoderma viride, strain TV1 (e.g. Trianum-P by Koppert);

(B2.54) Ampelomyces quisqualis, in particular strain AQ 10 (e.g. AQ 10® from IntrachemBio Italia);

(B2.56) Aureobasidium pullulans, in particular blastospores of strain DSM14940;

(B2.57) Aureobasidium pullulans, in particular blastospores of strain DSM 14941;

(B2.58) Aureobasidium pullulans, in particular blastospore mixtures of strains DSM14940 and DSM 14941 (e.g. Botector® from bio-ferm, CH);

(B2.64) Cladosporium cladosporioides, strain H39 (produced by Stichting Dienst Landbouwkundig Onderzoek);

(B2.69) Gliocladium catenulatum (Synonym: Clonostachys rosea f. catenulate) strain J1446 (e.g. Prestop® by AgBio Inc., and also e.g. Primastop® by Kemira Agro Oy);

(B2.70) Lecanicillium lecanii (formerly known as Verticillium lecanii) conidia strain KV01 (e.g. Vertalec® from Koppert/Arysta);

(B2.71) Penicillium vermiculatum;

(B2.72) Pichia anomala strain WRL-076 (NRRL Y-30842);

(B2.75) Trichoderma atroviride, strain SKT-1 (FERM P-16510);

(B2.76) Trichoderma atroviride, strain SKT-2 (FERM P-16511);

(B2.77) Trichoderma atroviride, strain SKT-3 (FERM P-17021);

(B2.78) Trichoderma gamsii (formerly T. viride), strain ICC080 (IMICC 392151 CABI, e.g. BioDerma from AGROBIOSOL DE MEXICO, S.A. DE C.V.);

(B2.79) Trichoderma harzianum, strain DB 103 (e.g. T-Gro 7456 from Dagutat Biolab);

(B2.80) Trichoderma polysporum, strain IMI 206039 (e.g. Binab TF WP manufactured by BINAB Bio-Innovation AB, Sweden);

(B2.81) Trichoderma stromaticum (e.g. Tricovab by Ceplac, Brazil);

(B2.83) Ulocladium oudemansii, in particular strain HRU3 (e.g. Botry-Zen® from Botry-Zen Ltd, New Zealand);

(B2.84) Verticillium albo-atrum (formerly V. dahliae), strain WCS850 (CBS 276.92, e.g. Dutch Trig from Tree Care Innovations);

(B2.86) Verticillium chlamydosporium;

(B2.87) mixtures of Trichoderma asperellum strain ICC 012 and Trichoderma gamsii strain ICC 080 (a product known, for example, as BIO-TAMTM manufactured by Bayer CropScience LP, USA).

Further examples of biological control agents that may be used in combination with the combination of compounds of the invention include the following:

bacteria selected from the group consisting of Bacillus cereus, in particular B. cereus strain CNCM I-1562 and Bacillus firmus strain I-1582 (CNCM accession number I-1582), Bacillus subtilis strain OST 30002 (NRRL accession number B-50421), Bacillus thuringiensis, in particular B. thuringiensis subsp. israelensis (serotype H-14), strain AM65-52 (ATCC accession number 1276), B. thuringiensis subsp. aizawai, in particular strain ABTS-1857 (SD-1372), B. thuringiensis subsp. kurstaki strain HD-1, B. thuringiensis subsp. tenebrionis strain NB 176 (SD-5428), Pasteuria penetrans, Pasteuria spp. (nematode Rotylenchulus reniformis)-PR3 (ATCC accession number SD-5834), Streptomyces microflavus strain AQ6121 (= QRD 31.013, NRRL B-50550) and Streptomyces galbus strain AQ 6047 (accession number NRRL 30232);

fungi and yeasts selected from the group consisting of Beauveria bassiana, in particular strain ATCC 74040, Lecanicillium spp., in particular strain HRO LEC 12, Metarhizium anisopliae, in particular strain F52 (DSM3884 or ATCC 90448), Paecilomyces fumosoroseus (now: Isaria jumosorosea), in particular strain IFPC 200613 or strain Apopka 97 (ATCC accession number 20874), and Paecilomyces lilacinus, in particular strain P.lilacinus 251 (AGAL 89/030550);

viruses selected from the group consisting of Adoxophyes orana (yellow leaf roller) granulosis virus (GV), Cydia pomonella (codling moth) granulosis virus (GV), Helicoverpa armigera (cotton leafworm) nuclear polyhedrosis virus (NPV), Spodoptera exigua (beet armyworm) mNPV, Spodoptera frugiperda (fall armyworm) mNPV and Spodoptera littoralis (African cotton leafworm) NPV.

bacteria and fungi which can be added as an inoculant to plants, plant parts or plant organs and which by virtue of their special properties promote plant growth and health. Examples: Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., in particular Burkholderia cepacia (formerly known as Pseudomonas cepacia), Gigaspora spp. or Gigaspora monosporum, Glomus spp., Laccaria spp., Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., in particular Rhizobium trifolii,

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Rhizopogon spp., Scleroderma spp., Suillus spp. and Streptomyces spp.;

plant extracts and microbial products including proteins and secondary metabolites that can be used as biological control agents such as Allium sativum, Artemisia absinthium, azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus angulatus, Chenopodium anthelminticum, chitin, Armour-Zen, Dryopteris filix-mas, Equisetum arvense, Fortune Aza, Fungastop, Heads Up (Chenopodium quinoa saponin extract), Pyrethrum/Pyrethrins, Quassia amara, Quercus, Quillaja, Regalia, Requiem™ Insecticide, rotenone, ryania/ryanodine, Symphytum officinale, Tanacetum vulgare, thymol, Triact 70, TriCon, Tropaeulum majus, Urtica dioica, veratrine, Viscum album, an extract of Brassicaceae, in particular oilseed rape powder or mustard powder.

Examples of insecticides, acaricides and nematicides that can be mixed with the composition of compounds according to the invention include the following:

(1) Acetylcholinesterase (AChE) inhibitors such as, for example, carbamates, for example, alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formatenate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiophanox, triazamate, trimethacarb, XMC, xylylcarb; or organophosphates such as acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyphos, chlorfenvinphos, chlormephos, chlorpyrifos-methyl, coumaphos, cyanofenphos, demeton-S-methyl, diazinon, dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprofos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imiciafos, isofenphos, isopropyl O-(methoxyaminothiophosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion-methyl, phentoate, phorate, fosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propafos, propetamphos, prothiophos, pyraclofos, pyridafention, quinalfos, sulfotep, tebupirimphos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, lorfon, vamidotion.

(2) GABA-gated chloride channel blockers such as, for example, cyclodiene organochlorine compounds, for example, chlordane and endosulfan, or phenylpyrazoles (fiproles), for example, ethiprole and fipronil.

(3) Sodium channel modulators such as, for example, pyrethroids, for example, acrinathrin, allethrin, d-cis-trans-allethrin, d-trans-allethrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambdacyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(III)-trans-isomer], deltamethrin, empenthrin [(EZ)-(1R)-isomer], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, cadetrin, momfluorothrin, permethrin, phenothrin [(III)-trans-isomer], prallethrin, pyrethrins (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(III)-isomer)], tralomethrin and transfluthrin or DDT or methoxychlor.

(4) Competitive nicotinic acetylcholine receptor (nAChR) modulators such as, for example, neonicotinoids, such as acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam, or nicotine, or sulfoxaflor, or flupyradifurone.

(5) Allosteric modulators of nicotinic acetylcholine receptors (nAChR), such as spinosyns, such as spinetoram and spinosad.

(6) Allosteric modulators of glutamate-gated chloride channels (GluCl), such as, for example, avermectins/milbemycins, for example, abamectin, emamectin benzoate, lepimectin and milbemectin.

(7) Juvenile hormone mimetics, such as, for example, juvenile hormone analogues, such as hydroprene, kinoprene and methoprene, or fenoxycarb, or pyriproxyfen.

(8) Various non-specific (multi-site) inhibitors, such as, for example, alkyl halides, for example methyl bromide and other alkyl halides; or chloropicrin, or sulfuryl fluoride, or borax, or potassium antimonyl tartrate, or methyl isocyanate generators, for example diazomet and metam.

(9) Chordotonal organ modulators, such as pymetrozine or flonicamid.

(10) Mite growth inhibitors such as clofentezine, hexythiazox and difluvidazine or etoxazole.

(11) Insect intestinal membrane microbial disruptors, such as Bacillus thuringiensis subsp israelensis, Bacillus sphaericus, Bacillus thuringiensis subsp aizawai, Bacillus thuringiensis subsp kurstaki, Bacillus thuringiensis subsp tenebrionis, and plant B.t. proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cmy34Ab1/35Ab1.

(12) Mitochondrial ATP synthase inhibitors such as ATP depleters such as, for example, diafenthiuron or organotin compounds such as azocyclotin oxide, cyhexatin and fenbutatin, or propargite or tetradifon.

(13) Agents that promote bond breaking during oxidative phosphorylation by disrupting the proton gradient, such as chlorfenapyr, DNOC and sulfluramid.

(14) Nicotinic acetylcholine receptor channel blockers, such as bensultap,

- 12 047972 cartap hydrochloride, thiocylam and thiosultap sodium.

(15) Chitin biosynthesis inhibitors type 0, such as, for example, bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.

(16) Chitin biosynthesis inhibitors type 1, such as buprofezin.

(17) A moult disruptor (particularly for Diptera, i.e. dipterans), such as, for example, cyromazine.

(18) Ecdysone receptor agonists such as chromafenozide, halofenozide, methoxyfenozide and tebufenozide.

(19) Octopamine receptor agonists such as amitraz.

(20) Profluazole of mitochondrial complex III electron transfer, such as, for example, hydramethylnon, or acequinocyl, or fluacrypyrim.

(21) Mitochondrial complex I electron transfer inhibitors from the METI group of acaricides, such as fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad or rotenone (Denis).

(22) Voltage-regulated sodium channel blockers such as indoxacarb or metaflumizone.

(23) Acetyl-CoA carboxylase inhibitors such as, for example, tetronic and tetramic acid derivatives, such as spirodiclofen, spiromesifen and spirotetramat.

(24) Mitochondrial complex IV electron transfer inhibitors such as, for example, phosphines, such as aluminum phosphide, calcium phosphide, phosphine and zinc phosphide, or cyanides, such as calcium cyanide, potassium cyanide and sodium cyanide.

(25) Mitochondrial complex II electron transfer inhibitors such as, for example, beta-ketonitrile derivatives such as cyenopyrafen and cyflumetofen and carboxanilides such as, for example, piflumide.

(28) Ryanodine receptor modulators such as, for example, diamides, for example chlorantraniliprole, cyantraniliprole and flubendiamide, additional active compounds such as, for example, afidopyropene, afoxolaner, azadirachtin, benclothiaz, benzoximate, bifenazate, broflanilide, bromopropylate, quinomethionate, chlorprallethrin, cryolite, cyclaniliprol, cycloxapride, cyhalodiamide, diclomesothiaz, dicofol, epsilon-metofluthrin, epsilon-momfluthrin, flometoquine, fluazaindolisine, fluensulfone, flufenerim, flufenoxystrobin, flufiprole, fluhexafon, fluopyram, fluralaner, fluxamethamide, fufenozide, guadipyr, heptafluthrin, imidaclotise, iprodione, kappa-bifenthrin, kappa-tefluthrin, lotilaner, meperfluthrin, paihongding, pyridalyl, pyrifluquinazone, pyriminostrobin, spirobudiclofen, tetramethylfluthrin, tetraniliprol, tetrachlorantraniliprole, tigolaner, tioxazafen, thiofluoximate, triflumezopyrim and iodomethane; in addition, Bacillus firmus-based products (I-1582, BioNeem, Votivo), as well as the following compounds:

1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-3-(trifluoromethyl)-III-1,2,4-triazol-5-amine (known from WO 2006/043635) (CAS 885026-50-6), {1'-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]-5-fluorospiro[indole-3,4'-piperidine]-1(2H)-yl}(2-chloropyridin-4-yl)methanone (known from WO 2003/106457) (CAS 637360-23-7),

2-chloro-N-[2-{1-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]piperidin-4-yl}-4-(trifluoromethyl)phenyl]isonicotinamide (known from WO 2006/003494) (CAS 872999-66-1),

3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one (known from WO 2010052161) (CAS 1225292-17-0),

3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-yl ethyl carbonate (known from EP2647626) (CAS 1440516-42-6),

4-(but-2-yn-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine (known from

WO2004/099160) (CAS 792914-58-0), PF1364 (known from JP2010/018586) (CAS 1204776-60-2), N[(2E)-1-[(6-chloropyridin-3-yl)methyl]pyridin-2(III)-ylidene]-2,2,2-trifluoroacetamide (known from WO 2012/029672) (CAS 1363400-41-2), (3E)-3-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-1,1,1-trifluoro-propan-2-one (known from

WO 2013/144213) (CAS 1461743-15-6), N-[3-(benzylcabamoyl)-4-chlorophenyl]-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-III-pyrazole-5-carboxamide (known from WO 2010/051926) (CAS 1226889-14-0),

5-bromo-4-chloro-N-[4-chloro-2-methyl-6-(methylcabamoyl)phenyl]-2-(3-chloro-2-pyridyl)pyrazole-3-carboxamide (known from CN103232431) (CAS 1449220-44-3),

4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxido-3-thietanyl)benzamide,

4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-{trans-1-oxido-3-thietanyl)benzamide and

4-[^)-5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1oxido-3-thietanyl)benzamide (known from WO 2013/050317 A1) (CAS 1332628-83-7),

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N-[3 -chloro-1 -(3 -pyridinyl)-1H-pyrazol-4-yl] -H-ethyl-3-[(3,3,3-tri(|)thorpropyl)sul(|)inyl| propanamide, (+)-N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl] propanamide and (-)-N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl] propanamide (known from WO 2013/162715 A2, WO 2013/162716 A2, US 2014/0213448 A1) (CAS 1477923-37-7),

5-[[(2E)-3-chloro-2-propen-1-yl]amino]-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile (known from CN 101337937 A) (CAS 1105672-77-2),

-bromo-N-[4-chloro-2-methyl-6-[(methylamino)thiochomethyl]phenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide (Liudaibenjiaxuanan, known from CN 103109816 A) (CAS 1232543-85-9), N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-3(fluoromethoxy)-1H-pyrazole-5-carboxamide (known from WO 2012/034403 A1) (CAS 1268277-22-0), N[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1Hpyrazole-5-carboxamide (known from WO 2011/085575 A1) (CAS 1233882-22-8), 4-[3-[2,6-dichloro-4-[(3,3-dichloro-2-propen-1-yl)oxy]phenoxy]propoxy]-2-methoxy-6(trifluoromethyl)pyrimidine (known from CN 101337940 A) (CAS 1108184-52-6), (2E)- and 2^)-2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-H-[4-(difluoromethoxy)phenyl]hydrazinecarboxamide (known from CN 101715774 A) (CAS 1232543-85-9), 3-(2,2-dichloroethenyl)-2,2-dimethyl-4-(1H-benzimidazol-2yl)phenyl cyclopropane carboxylic acid ester (known from CN 103524422 A) (CAS 1542271-46-4), methyl ester (4aS)-7-chloro-2,5-dihydro-2-[[(methoxycarbonyl)[4-[(trifluoromethyl)thio]phenyl]amino]carbonyl]indeno[1,2-e][1,3,4]oxadiazine-4a(3H)-carboxylic acid (known from CN 102391261 A) (CAS 1370358-69-2),

6-deoxy-3-O-ethyl-2,4-di-O-methyl-,

1-[N[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1H-1,2,4-triazol-3-yl]phenyl]carbamate]-a-b-mannopyranose (known from US 2014/0275503 A1) (CAS 1181213-14-8),

8-(2-cyclopropylmethoxy-4-trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3-azabicyclo[3.2.1]octane (CAS 1253850-56-4), (8-anti)-8-(2-cyclopropylmethoxy-4-trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3aza-bicyclo[3.2.1]octane (CaS 933798-27-7), (8-anti)-8-(2-cyclopropylmethoxy-4-trifluoromethylphenoxy)-3-(6-trifluoromethylpyridazin-3-yl)-3aza-bicyclo[3.2.1]octane (known from WO 2007040280 A1, WO 2007040282 A1) (CAS 934001-66-8),

N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)thio]propanamide (known from WO 2015/058021 A1, WO 2015/058028 A1) (CAS 1477919-27-9) and N-[4-(aminothiochomethyl)-2-methyl-6-[(methylamino)carbonyl]phenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide (known from CN 103265527 A) (CAS 1452877-50-7),

5-(1,3-diohap-2-yl)-4-[[4-(trifluoromethyl)phenyl]methoxy]pyrimidine (known from WO 2013/115391 A1) (CAS 1449021-97-9),

3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-1-methyl-1,8-diazaspiro[4.5]dec-3-en-2-one (known from WO 2010/066780 A1, WO 2011/151146 A1) (CAS 1229023-34-0),

3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-1,8-diazaspiro[4.5]decane-2,4-dione (known from WO 2014/187846 A1) (CAS 1638765-58-8),

-(4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-yl carbonate ester (known from WO 2010/066780 A1, WO 2011/151146 A1) (CAS 1229023-00-0), N-[1-[(6-chloro-3-pyridinyl)methyl]-2(1H)pyridinylidene]-2,2,2-trifluoroacetamide (known from DE 3639877 A1, WO 2012/029672 A1) (CAS 1363400-41-2),

[N(E)]-Ы-[1-[(6-chloro-3-pyridinyl)methyl]-2(1H)-pyridinylidene]-2,2,2-trifluoroacetamide, (known from WO 2016/005276 A1) (CAS 1689566-03-7),

[N(Z)]-Ы-[1-[(6-chloro-3-pyridinyl)methyl]-2(1H)-pyridinylidene]-2,2,2-trifluoroacetamide, (CAS

1702305-40-5), 3-endo-3-[2-propoxy-4-(trifluoromethyl)phenoxy]-9-[[5-(trifluoromethyl)-2-pyridinyl]oxy]-9azabicyclo[3.3.1]nonane (known from WO 2011/105506 A1, WO 2016/133011 A1) (CAS 1332838-17-1).

Examples of safeners that can be mixed with the combination of compounds according to the invention are, for example, benoxacor, cloquintocet(-mexyl), cyometrinil, cyprosulfamide, dichlormide, fenchlorazole(-ethyl), fenclorim, flurazole, fluxofenim, furilazole, isoxadifen(-ethyl), mefenpyr(-diethyl), naphthalic anhydride, oxabetrinil, 2-methoxy-N-({4-[(methylcarbamoyl)amino]phenyl}sulfonyl)benzamide (CAS 129531-12-0), 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS 52836-31-4).

Examples of herbicides that can be mixed with the composition of compounds according to the invention include the following:

Acetochlor, Acifluorfen, Acifluorfen Sodium, Aclonifen, Alachlor, Allidochlor, Alloxydime, Aloxydime Sodium, Ametryn, Amicarbazone, Amidochlor, Amidosulfuron, 4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, Aminocyclopyrachlor, Aminocyclopyrachlorpotassium, Aminocyclopyrachlor-methyl, Aminopyralid, Amitrol, Ammonium Sulfamate, Anilofos, Asulam, Atrazine, Azaphenidine, Azimsulfuron, Beflubutamide, Benazolin, Benazolin-ethyl, Benfluralin, Benfuresate, bensulfuron, bensulfuron-methyl, bensulide, bentazone, benzobicyclone, benzofenap, bicyclopyrone, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxime, bromoxynil, bromoxynil butyrate, potassium, -heptanoate and -octanoate, butoxynone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chlorbromuron, chlorfenac, chlorfenac-sodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazone, chlorimuron, chlorimuron-ethyl, chlorphthalim, chlortoluron, chlorthal-dimethyl, chlorsulfuron, cinidon, cinidon-ethyl, cinmethylin, cinosulfuron, clacifos, clethodim, clodinafop, clodinafop-propargyl, clomazone, clomeprop, clopyralid, cloransulam, cloransulam-methyl, cumiluron, cyanamide, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, ciprazine, 2,4-D, 2,4-O-butothyl. -butyl, -dimethylammonium, -diolamine, -ethyl, -2-ethylhexyl, -isobutyl, -isooctyl, -isopropylammonium, -potassium, -triisopropanolammonium and -trolamine, 2,4-DB, 2,4-OB-butyl, -dimethylammonium, -isooctyl, -potassium and -sodium, daimuron (dimron), dalapon, dazomet, n-decanol, desmedipham, detosyl pyrazolate (DPT), dicamba, dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, dichlorprop, dichlorprop-R, diclofop, diclofop-methyl, diclofop-R-methyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr sodium, dimefuron, dimepiperate, dimethachlor, dimetamethrin, dimethenamid, dimethenamid-R, dimetrasulfuron, dinitramine, dinoterb, diphenamide, diquat, diquat-dibromide, dithiopyr, diuron, dinitroorthocresol, endothal, ethyl-N, N-di-npropylthiocarbamate, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, etiosin, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanide, F-9600, F-5231, i.e. No. {2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-5-oxo-4,5-dihydro-1H-tetrazol-1-yl]phenyl}ethanesulfonamide, F-7967, i.e. 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine2,4(1H,3H)-dione, fenoxaprop, fenoxaprop-R, fenoxaprop-ethyl, fenoxaprop-R-ethyl, fenoxasulfone, fenquinotrione, fentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-R, fluazifop-butyl, fluazifop-R-butyl, flucarbazone, flucarbazone sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, dimethylammonium and -methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate, glufosinate-aminium, glufosinate-P-sodium, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-ammonium, -isopropylammonium, -diammonium, -dimethylammonium, -potassium, -sodium and -trimesium, H-9201, i.e. O-(2,4-dimethyl-6-nitrophenyl) O-ethyl propyl isophosphoramidothioate, haloxyfen, haloxyfen-methyl, halsafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HW02, i.e. 1-(dimethoxyphosphoryl) ethyl-(2,4-dichlorophenoxy)acetate, imazamethabenz, imazamethabenzmethyl, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, imazapyrizopropylammonium, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-immonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxynyl-octanoate, -potassium and -sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, carbutylate, KUH-043, i.e. 3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl4,5-dihydro-1,2-oxazole, ketospiradox, lactofen, lenacyl, linuron, MCFC, MCFC-butothyl, -dimethylammonium, -2-ethylhexyl, -isopropyl monium, -potassium and -sodium, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-sodium and -butotyl, mecoprop-R, mecoprop-R-butotyl, -dimethylammonium, -2-ethylhexyl and -potassium, mefenacet, mefluidide, mesosulfuron-methyl, mesotrione, metabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron, metabenzthiazuron, methiopyrsulfuron, methiozolin, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metosulam, metribuzin, metsulfuron, metsulfuron-methyl, molinate, monolinuron, monosulfuron, monosulfuron-ether, MT-5950, i.e., N-(3-chloro-4-isopropylphenyl)-2-methylpentanamide, NGGC-011, napropamide, NC-310, i.e., [5-(benzyloxy)-1-methyl-1H-pyrazol-4-yl](2,4-dichlorophenyl)methanone, neburon, nicosulfuron, nonanoic acid (pelargonic acid), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazone, oxasulfuron, oxacyclomefon, oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorophenol, pentoxazone, petoxamide, petroleum oils, phenmedipham, picloram, picolinafen, pinoxaden, piperofos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, profam, propochlor, propoxycarbazone, propoxycarbazone sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotol, pyrazolinate (pyrazolate), pyrazosulfuron, pyrazosul- 15 047972 furon-ethyl, pyrazoxyfene, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, ruribenzoxime, pyributicarb, pyridafol, pyridate, pyriftalide, pyrimnobac, pyrimimnobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinchlorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-R, quizalofop-R-ethyl, quizalofop-R-tefuryl, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simethrine, SL-261, sulcotrione, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron, SYN-523, SYP-249, i.e. 1-ethoxy-3-methyl-1-oxobut3-en-2-yl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate, SYP-300, i.e. 1-[7-fluoro-3-oxo-4-(prop-2yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidine-4,5-dione, 2,3,6-TBA, TCA (trichloroacetic acid), TCA sodium, tebuthiuron, tefuryltrione, tembotrin, tepraloxydim, terbacil, terbucarb, terbumetone, terbuthylazine, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, thiafenacil, tolpyralate, topramezone, tralkoxydim, triafamone, triallate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, triethazine, trifloxysulfuron, trifloxysulfuron sodium, trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea sulfate, vernolate, XDE-848, ZJ-0862, i.e. 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline and the following compounds:

o ^CO ₂ Et

Examples of plant growth regulators:

Acibenzolar, acibenzolar-^-methyl, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, brassinolide, catechin, chlormequat chloride, cloprop, cyclanilide, 3-(cycloprop-1-enyl)propionic acid, daminozide, dazomet, n-decanol, dikegulac, dikegulac sodium, endothal, endothaldicassium, -disodium and -mono(N-dimethylalkylammonium), ethephon, flumetralin, flurenol, flurenolbutyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid (IAA), 4-indol-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, hydrazide maleic acid, mepiquat chloride, 1-methylcyclopropene, methyl jasmonate, 2-(1-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenolate mixture, paclobutrazol, N-(2-phenylethyl)-beta-alanine, N-phenylphthalamic acid, prohexadione, prohexadione-calcium, prohydrojasmone, salicylic acid, strigolactone, teknazen, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, cytodef, uniconazole, uniconazole-R.

Methods and areas of application.

The present invention also relates to a method for combating unwanted microorganisms, in particular phytopathogenic fungi, which comprises treating the microorganisms and/or their habitat with a combination of compounds according to the present invention or a composition containing such a combination.

The present invention also relates to seeds that have been treated with a combination of compounds according to the invention or a composition containing such a combination.

Finally, the present invention provides a method for protecting seed from unwanted microorganisms by treating the seed with a combination of compounds according to the invention or a composition containing such a combination.

The combinations of compounds according to the invention or compositions containing such a combination have a strong bactericidal effect and can be used to combat unwanted microorganisms such as fungi and bacteria in the field of plant protection and material protection.

The combinations of compounds according to the invention or compositions containing such a combination have high fungicidal properties and can be used to protect crops, for example, to combat plasmodiophoromycetes, oomycetes, chytridiomycetes, zygomycetes, ascomycetes, basidiomycetes and deuteromycetes.

Bactericides can be used to protect crops against microorganisms of the families Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.

The combinations of compounds according to the invention or compositions containing such combinations can be used for treatment or preventive protection against phytopathogenic fungi. Thus, the invention also relates to methods of treatment and protection for combating phytopathogenic fungi by using the combinations or compositions according to the invention, which are used to treat seeds, plants or parts of plants, fruits or the soil in which the plants grow.

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Plants.

According to the present invention, all plants and parts thereof may be subject to treatment. In this case, plants are understood to mean all plants and plant populations, such as desirable and undesirable wild plants or agricultural crops (including free-growing agricultural crops). Agricultural crops may accordingly include plants that can be obtained by conventional plant breeding and optimization methods, or by biotechnology and genetic engineering methods, or by a combination of these methods, including transgenic plants and their varieties that may or may not be protected by plant breeders' rights. Parts of a plant are understood to mean parts and organs of a plant that are located above and below the ground, such as shoots, leaves, flowers and roots, as well as leaves, needles, peduncles, stems, flowers, fruiting bodies, fruits, seeds, roots, tubers and rhizomes. Parts of a plant also include harvested crops and material for plant and generative propagation, such as cuttings, tubers, rhizomes, shoots and seeds.

Plants that can be treated according to the invention include the following plants: cotton, flax, grapes, fruits, vegetables such as Rosaceae species (e.g. pome fruits such as apples and pears, as well as stone fruits such as apricots, cherries, almonds and peaches, as well as berry crops such as strawberries), Ribesioidae species, Juglandaceae, Betulaceae, Anacardiaceae, Fagaceae, Moraceae, Oleaceae, Actinidaceae, Lauraceae, Musaceae (e.g. banana trees and plantations), Rubiaceae (e.g. coffee), Theaceae, Sterculiceae, Rutaceae (e.g. lemons, oranges and grapefruits); Solanaceae (e.g. tomatoes), Liliaceae, Asteraceae (e.g. lettuce), Umbelliferae, Cruciferae, Chenopodiaceae, Cucurbitaceae (e.g. cucumber), Alliaceae (e.g. leeks, onions), Papilionaceae (e.g. peas); major agricultural crops such as Gramineae (e.g. maize, turf crops, cereals such as wheat, rye, rice, barley, oats, millet and triticale), Asteraceae (e.g. sunflower), Brassicaceae (e.g. cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, Chinese cabbage, kohlrabi, radishes and oilseed rape, mustard, horseradish and watercress), Fabacae (e.g. beans, peanuts), Papilionaceae (e.g. soybeans), Solanaceae (e.g. potatoes), Chenopodiaceae (e.g. sugar beet, fodder beet, Swiss chard, beetroot); useful and ornamental plants for gardens and forestry; and genetically modified varieties of these plants.

Pathogens.

Examples of fungal pathogens that can be treated according to the invention include, but are not limited to:

diseases caused by powdery mildew pathogens, such as Blumeria species, such as Blumeria graminis; Podosphaera species, such as Podosphaera leucotricha; Sphaerotheca species, such as Sphaerotheca fuliginea; Uncinula species, such as Uncinula necator;

diseases caused by rust pathogens, such as Gymnosporangium species, such as Gymnosporangium sabinae; Hemileia species, such as Hemileia vastatrix; Phakopsora species, such as Phakopsora pachyrhizi and Phakopsora meibomiae; Puccinia species, such as Puccinia recondite, Puccinia graminis or Puccinia striiformis; Uromyces species, such as Uromyces appendiculatus;

diseases caused by pathogens of the Oomycetes group, such as Albugo species, such as Albugo candida; Bremia species, such as Bremia lactucae; Peronospora species, such as Peronospora pisi or P. brassicae; Phytophthora species, such as Phytophthora infestans; Plasmopara species, such as Plasmopara viticola; Pseudoperonospora species, such as Pseudoperonospora humuli or Pseudoperonospora cubensis; Pythium species, such as Pythium ultimum;

leaf spot and wilt diseases caused by, for example, Alternaria species, e.g. Alternaria solani; Cercospora species, e.g. Cercospora beticola; Cladiosporium species, e.g. Cladiosporium cucumerinum; Cochliobolus species, e.g. Cochliobolus sativus (conidial form: Drechslera, syn.: Helminthosporium) or Cochliobolus miyabeanus; Colletotrichum species, e.g. Colletotrichum lindemuthanium; Cycloconium species, e.g. Cycloconium oleaginum; Diaporthe species, e.g. Diaporthe citri; Elsinoe species, e.g. Elsinoe fawcettii; Gloeosporium species, e.g. Gloeosporium laeticolor; Glomerella species, e.g. Glomerella cingulata; Guignardia species, e.g. Guignardia bidwelli; Leptosphaeria spp., such as Leptosphaeria maculans; Magnaporthe spp., such as Magnaporthe grisea; Microdochium spp., such as Microdochium nivale; Mycosphaerella spp., such as Mycosphaerella graminicola, Mycosphaerella arachidicola or Mycosphaerella fjiensis; Phaeosphaeria spp., such as Phaeosphaeria nodorum; Pyrenophora spp., such as Pyrenophora teres or Pyrenophora tritici repentis; Ramularia spp., such as Ramularia collo-cygni or Ramularia areola; Rhynchosporium spp., such as Rhynchosporium secalis; Septoria spp., such as Septoria apii or Septoria lycopersici; Stagonospora spp., such as Stagonospora nodorum; Typhula spp., such as Typhula incarnata; Venturia species, such as Venturia inaequalis;

root and stem diseases caused by, for example, Corticium species, such as Corticium graMunarum; Fusarium species, such as Fusarium oxysporum; Gaeumannomyces species, such as Gaeumannomyces graminis; Plasmodiophora species, such as Plasmodiophora brassicae;

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Rhizoctonia, such as Rhizoctonia solani; Sarocladium species, such as Sarocladium oryzae; Sclerotium species, such as Sclerotium oryzae., Tapesia species, such as Tapesia acuformis; Thielaviopsis species, such as Thielaviopsis basicola;

ear and panicle diseases (including ears of maize) caused by, for example, Alternaria species, e.g. Alternaria spp.; Aspergillus species, e.g. Aspergillus flavus; Cladosporium species, e.g. Cladosporium cladosporioides; Claviceps species, e.g. Claviceps purpurea; Fusarium species, e.g. Fusarium culmorum; Gibberella species, e.g. Gibberella zeae; Monographella species, e.g. Monographella nivalis; Stagnospora species, e.g. Stagnospora nodorum;

diseases caused by smut fungi, such as Sphacelotheca species, such as Sphacelotheca reiliana; Tilletia species, such as Tilletia caries or Tilletia controversa; Urocystis species, such as Urocystis occulta; Ustilago species, such as Ustilago nuda;

fruit rot caused by, for example, Aspergillus species, such as Aspergillus flavus; Botrytis species, such as Botrytis cinerea; Penicillium species, such as Penicillium expansum or Penicillium purpurogenum; Rhizopus species, such as Rhizopus stolonifer; Sclerotinia species, such as Sclerotinia sclerotiorum; Verticilium species, such as Verticilium alboatrum;

Seed-borne and soil-borne rot and wilt diseases and seedling diseases caused by, for example, Alternaria species, e.g. Alternaria brassicicola; Aphanomyces species, e.g. Aphanomyces euteiches; Ascochyta species, e.g. Ascochyta lentis; Aspergillus species, e.g. Aspergillus flavus; Cladosporium species, e.g. Cladosporium herbarum; Cochliobolus species, e.g. Cochliobolus sativus (conidial form: Drechslera, Bipolaris Syn.: Helminthosporium); Colletotrichum species, e.g. Colletotrichum coccodes; Fusarium species, e.g. Fusarium culmorum; Gibberella species, e.g. Gibberella zeae; Macrophomina species, e.g. Macrophomina phaseolina; Microdochium species, e.g. Microdochium nivale; Monographella spp., such as Monographella nivalis; Penicillium spp., such as Penicillium expansum; Phoma spp., such as Phoma lingam; Phomopsis spp., such as Phomopsis sojae; Phytophthora spp., such as Phytophthora cactorum; Pyrenophora spp., such as Pyrenophora graminea; Pyricularia spp., such as Pyricularia oryzae; Pythium spp., such as Pythium ultimum; Rhizoctonia spp., such as Rhizoctonia solani; Rhizopus spp., such as Rhizopus oryzae; Sclerotium spp., such as Sclerotium rolfsii; Septoria spp., such as Septoria nodorum; Typhula spp., such as Typhula incarnata; Verticillium spp., such as Verticillium dahliae;

crayfish, galls and witches' broom, caused for example by Nectria species, such as Nectria galligena;

wilt diseases caused, for example, by Monilinia species, such as Monilinia laxa;

deformations of leaves, flowers and fruits caused by, for example, Exobasidium species, such as Exobasidium vexans; Taphrina species, such as Taphrina deformans;

degenerative diseases of woody plants caused, for example, by Esca species, such as Phaeomoniella chlamydospora, Phaeoacremonium aleophilum or Fomitiporia mediterranean Ganoderma species, such as Ganoderma boninense;

diseases of flowers and seeds caused, for example, by Botrytis species, such as Botrytis cinerea;

diseases of plant tubers caused, for example, by species of the genus Rhizoctonia, for example Rhizoctonia solani; species of the genus Helminthosporium, for example Helminthosporium solani;

diseases caused by bacterial pathogens, such as Xanthomonas species, such as Xanthomonas campestris pv. oryzae; Pseudomonas species, such as Pseudomonas syringae pv. lachrymans; Erwinia species, such as Erwinia amylovora.

Preferably, the compounds of the invention can be used to control the following soybean diseases:

fungal diseases of leaves, stems, pods and seeds, such as Alternaria leaf spot (Alternaria spec, atrans tenuissima), anthracnose (Colletotrichum gloeosporoides dematium var. truncatum), rust spot (Septoria glycines), cercospora leaf spot (Cercospora kikuchii), choanephora leaf spot (Choanephora infundibulifera trispora (Syn.)), dactuliophora leaf spot (Dactuliophora glycines), downy mildew (Peronospora manshurica), drexlera wilt (Drechslera glycint), soybean spot (Cercospora sqjina), leptospherulina leaf spot (Leptosphaerulina trifolii), Phyllosticta leaf spot (Phyllosticta sqjaecola), soybean stem and bean blight (Phomopsis sojae), powdery mildew (Microsphaera diffusa), Pyrenochaeta leaf spot (Pyrenochaeta glycines), Rhizoctonia solani, rust (Phakopsora pachyrhizi, Phakopsora meibomiae), scab (Sphaceloma glycines), Stemphylium leaf wilt (Stemphylium botryosum), Corynespora cassiicold;

fungal diseases of roots and stem bases, such as black root rot (Calonectria crotalariae), charcoal rot (Macrophomina phaseolina), fusarium wilt, root rot and pod and crown rot (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti), root rot caused by Mycoleptodiscus species (Mycoleptodiscus terrestris),

- 18 047972 neocosmospora (Neocosmospora vasinfecta), bean and stem rot (Diaporthe phaseolorum), stem cancer (Diaporthe phaseolorum var. caulivora), late blight (Phytophthora megasperma), brown rot of soybean stems (Phialophora gregata), fungal rot (Pythium aphanidermatum, Pythium irregulare, Pythium debaryanum, Pythium myriotylum, Pythium ultimum), rhizoctonia, felt disease and damping-off (Rhizoctonia solani), sclerotinia leaf spot (Sclerotinia sclerotiorum), sclerotinia southern rot (Sclerotinia rolfsii), root rot caused by Thielaviopsis species (Thielaviopsis basicola).

Preferably, the compounds of the invention can also be used to control leaf spot and wilt diseases, as well as root and stem diseases of fruits and vegetables.

Regulation of plant growth.

In some cases, the combinations of compounds according to the invention and compositions containing such a combination, at a certain concentration or dosage, can be used as growth regulators or agents that improve plant characteristics.

The use of growth regulators may have different effects on plants. The effect of such substances depends largely on the time of application relative to the plant's development stage, as well as on the amounts of active ingredient that are applied to the plants or introduced into the plant's growing environment, as well as on the type of treatment or application. In each case, growth regulators must have a specific target effect on agricultural crops.

Growth regulating effects include earlier germination, improved emergence, more developed root system and/or improved root growth, improved tillering ability, more productive tillers, earlier flowering, increased plant height and/or biomass, shorter stems, improved tiller growth, number of grains per spike, number of spikes per 1 ^m2 , number of stolons and/or number of flowers, improved yield index, larger leaf size, less dead basal leaves, improved leaf arrangement, earlier maturity/earlier fruiting, uniform maturity, increased duration of grain filling, improved fruit maturity, increased fruit/vegetable size, resistance to germination, and reduced lodging.

The term increased yield or improved yield refers to total biomass per hectare, yield per hectare, stone/fruit ratio, seed size and/or hectolitre weight, and improved product quality including the following characteristics: improved processing suitability in terms of size distribution (e.g. of kernels or fruits), uniform ripening, grain moisture content, improved milling characteristics, improved vinification characteristics, improved brewing characteristics, increased juice yield, improved harvesting characteristics, digestibility, sedimentation number, falling number, pod stability, storage stability, improved fibre length/strength/uniformity, improved milk and/or meat quality in silage-fed animals, adaptation to cooking and roasting; also including improved commercial qualities in terms of improved fruit/grain quality, size distribution (e.g. of grains or fruits), increased shelf life/shelf life, firmness/softness, flavour (aroma, texture), grade (size, shape, number of berries), number of berries/fruits per bunch, crispness, freshness, wax coating, incidence of physiological disorders, colour; also including increased levels of target ingredients such as protein content, fatty acid content, oil content, oil quality, amino acid composition, sugar content, acid content (pH), sugar/acid ratio (Brix), polyphenols, starch content, nutritional value, gluten content, energy content, palatability; also including reduced levels of undesirable ingredients such as lower mycotoxins, lower aflatoxins, geosmin levels, aromatic and phenolic components, laccase, polyphenol oxidase and peroxidase, nitrate levels.

Plant growth regulator compounds can be used, for example, to slow down the vegetative growth of plants. Such growth suppression is of economic interest, for example, for turf crops, since it is possible to reduce the frequency of grass mowing in ornamental gardens, parks and sports fields, on roadsides, at airports or in areas with fruit crops. Growth suppression is also important for herbaceous and woody plants grown on roadsides, near pipelines or overhead lines or, in general, in places where vigorous plant growth is undesirable.

Of great importance is also the use of growth regulators to suppress the longitudinal growth of cereal crops. This reduces or completely eliminates the risk of lodging of plants before harvest. In addition, when using growth regulators, the stems of cereals can be strengthened, which also reduces the risk of lodging. When using growth regulators to strengthen and shorten the stems of cereals, it is possible to apply large volumes of fertilizers to increase the yield without the risk of lodging.

For many agricultural crops, suppression of vegetative development of plants is ensured

- 19 047972 allows for higher density planting, so that a larger harvest can be obtained on the same area. Another advantage of smaller plants obtained in this way is that it is easier to cultivate the plants and harvest the crop.

By reducing the vegetative development of plants, it is also possible to increase or improve the yield, since in this case a more efficient consumption of nutrients and assimilates is ensured for the formation of flowers and fruits, and not for the growth of vegetative parts of plants.

Alternatively, growth regulators can also be used to stimulate vegetative development. This is very useful when the vegetative parts of the plant are harvested. However, when vegetative development is stimulated, generative development can also be stimulated, since in this case more assimilates are formed, which leads to the formation of more fruits or to the formation of larger fruits.

In addition, positive effects on plant growth or yield can be achieved by improving nutrient use efficiency, particularly nitrogen (N) use efficiency, phosphorus (P) use efficiency, water use efficiency, improving transpiration, respiration rate and/or CO2 assimilation, improving nodulation, improving Ca metabolism.

Similarly, growth regulators can be used to change the composition of plants, which in turn can lead to improved crop quality. Growth regulators can influence the formation of parthenocarpic fruits. In addition, it is possible to influence the sex of the flower. It is also possible to obtain sterile pollen, which is important for breeding and obtaining hybrid seeds.

By using growth regulators, it is possible to control the branching of plants. On the other hand, by disturbing apical dominance, it is possible to stimulate the development of lateral shoots, which may be desirable especially in the cultivation of ornamental plants, also in combination with growth suppression. On the other hand, it is also possible to suppress the growth of lateral shoots. This effect is of particular interest, for example, in the cultivation of tobacco or tomatoes.

Under the influence of growth regulators, the number of leaves on plants can be controlled so that defoliation occurs at the right time. Such defoliation plays an important role in mechanical harvesting of cotton, but also in harvesting other crops, such as grapes. Plant defoliation can also be carried out to reduce transpiration in plants before transplanting.

In addition, growth regulators can modulate plant senescence, which can lead to an increase in the duration of the green leaf period, an increase in the grain filling phase, and an increase in crop quality.

Growth regulators can also be used to regulate fruit opening. On the other hand, premature fruit opening can be prevented in this way. On the other hand, fruit opening or even underdevelopment of the flower can be stimulated to achieve the required mass (thinning of the ovaries). In addition, growth regulators can be used to separate the fruits from the plant during harvesting with less physical force to enable mechanical harvesting or to facilitate manual harvesting.

Growth regulators can also be used to achieve earlier or later ripening of the harvested material before or after harvest. This is particularly important, as it allows for better adaptation to market demands. In addition, in some cases, growth regulators can improve the colour of the fruit. In addition, growth regulators can also be used to ensure that ripening occurs over a certain period of time. In this way, the necessary conditions are created to enable mechanical or manual harvesting in one step, for example in the case of tobacco, tomatoes or coffee.

In addition, by using plant growth regulators, it is possible to influence the dormancy period of seeds or buds of plants so that, for example, germination, shoot formation, flowering of plants such as pineapple or ornamental plants in nurseries occurs at times when this is not usual. In areas where there is a high probability of frost, it is desirable to delay bud break or seed germination by using growth regulators in order to avoid damage due to late frosts.

Finally, growth regulators can make plants resistant to low temperatures, drought or soil salinity. This allows for the cultivation of plants in areas that are usually unsuitable for such purposes.

Imparting plant resistance/vitality and other effects.

The combinations of compounds according to the invention and compositions containing such combinations also exhibit a strong strengthening effect on plants. Accordingly, they can be used to mobilize the plant's defense system against attack by harmful microorganisms.

In the context of the present invention, substances that increase plant viability (impart resistance to plants) are understood to mean substances that are capable of stimulating the plant's defense system in such a way that the treated plants subsequently, when inoculated with time,

- 20 047972 informing microorganisms would develop a high degree of resistance to these microorganisms.

Also in the context of the present invention, the physiological characteristics of a plant include the following:

abiotic stress tolerance, which includes tolerance to high or low temperatures, drought tolerance and the ability to recover from stressful drought conditions, water use efficiency (which is associated with reduced water consumption), flood tolerance, ozone stress and UV tolerance, tolerance to chemicals such as heavy metals, salts, pesticides;

resistance to abiotic stress, which includes increased resistance to fungi and increased resistance to nematodes, viruses and bacteria. In the context of the present invention, resistance to abiotic stress preferably includes increased resistance to fungi and increased resistance to nematodes;

increased plant vigor, including increased plant vigor/quality and increased seed germination vigor, reduced lodging susceptibility, improved appearance, increased ability to recover from stress conditions, improved pigmentation (e.g. chlorophyll content, improved ability to retain green colour) and improved photosynthetic efficiency.

Mycotoxins.

In addition, the combinations of compounds of the present invention and compositions containing such combinations can reduce the content of mycotoxins in harvested material and in food and feed products obtained therefrom. In particular, mycotoxins include, but are not limited to, the following substances: deoxynivalenol (DON), nivalenol, 15-Ac-DON, 3-Ac-DON, T2- and HT2-toxin, fumonisins, zearalenone, moniliformin, fusarin, diacetooxyscirpenol (DAS), beauvericin, enniatin, fusaroproliferin, fusarenol, ochratoxin, patulin, ergot alkaloids and aflatoxins, which can be produced, for example, by the following fungi: Fusarium species such as F. acuminatum, F. asiaticum, F. avenaceum, F. crookwellense, F. culmorum, F. gramunarum (Gibberella zeae), F. equiseti, F. fujikoroi, F. musarum, F. oxysporum, F. prolifemtum, F. poae, F. pseudogramunarum, F. sambucinum, F. scirpi, F. semitectum, F. solani, F. sporotrichoides, F. langsethiae, F. subglutinans, F. tricinctum, F. verticillioides, as well as Aspergillus species such as A. flavus, A. parasiticus, A. nomius, A. ochmceus, A. clavatus, A. terreus, A. versicolor, Penicillium species such as P. verrucosum, P. viridicatum, P. citrinum, P. expansum, P. claviforme, P. roqueforti, Claviceps species such as C. purpurea, C. fusiformis, C. paspali, C. africana, Stachybotrys species and others.

Protection of materials.

The combinations of compounds according to the invention and compositions containing such combinations can also be used for the protection of industrial materials, for the protection of industrial materials from the effects of phytopathogenic fungi and destruction by phytopathogenic fungi.

In addition, the combinations of compounds according to the invention and compositions containing such combinations can be used as antifouling compositions, alone or in combination with other active ingredients.

In the context of the present invention, the term industrial materials refers to non-living materials that are intended for use in industry. For example, industrial materials that can be protected using the compositions of the invention from changes or destruction due to the action of microorganisms can be adhesives, glues, paper, wallpaper and boards/cardboard, textiles, carpets, leather, wood, fibrous mass and fabrics, paint and plastic products, lubricating and cooling liquids and other materials that can be affected or destroyed by microorganisms. Also, among the materials that can be protected according to the invention, there can be mentioned parts of production plants and buildings, such as cooling water circulation circuits, cooling and heating systems, as well as ventilation and air conditioning units that can be destroyed due to the development of microorganisms. Industrial materials according to the present invention preferably include adhesives, glues, paper and cardboard, leather, wood, paint, cutting fluids and heat exchange fluids, more preferably wood.

The combinations of compounds according to the invention and compositions containing such combinations can prevent negative effects such as rotting, spoilage, discoloration, discolouration or mold formation.

In the case of wood treatment, the combination of compounds according to the invention and compositions containing such a combination can also be used against fungal diseases that can develop on the surface or inside timber. The term timber means all types of wood species and all types of treated timber intended for construction, such as solid wood, high-density timber, laminated timber and plywood. The method for treating timber according to the invention essentially consists in contact with the composition according to the invention; this includes, for example, direct application, spraying, dressing by the method

- 21 047972 immersion, injection or any other appropriate methods.

In addition, the combinations of compounds according to the invention and compositions containing such a combination can be used to protect against biofouling of objects that come into contact with mineralized or salt water, in particular ship hulls, screens, nets, buildings, mooring areas and signal systems.

The combinations of compounds according to the present invention and compositions containing such a combination can also be used for the protection of stored products. The term storage goods means natural substances of plant or animal origin and products of natural origin obtained by processing them, for which long-term protection is required. Storage goods of plant origin include, for example, plants or parts thereof, such as stems, leaves, tubers, seeds, fruits or grain, which can be protected in a freshly harvested state or in a processed form, for example, by pre-drying, moistening, crushing, grinding, pressing or high-temperature treatment. Storage goods also include timber, both raw timber, such as construction timber, power transmission line poles and fences, and timber in the form of finished products, such as furniture. Storage goods of animal origin are, for example, skins, leather, fur products and products made of fur hair. The compositions of the invention can prevent adverse effects such as rotting, spoilage, discoloration, discolouration, or mold formation.

Microorganisms which are capable of spoiling industrial materials or changing their properties include, for example, bacteria, fungi, yeasts, algae and sludge-dwelling organisms. The compounds of formula (I) preferably have an action on fungi, in particular on moulds, on fungi which cause discolouration or decay of wood (Ascomycetes, Basidiomycetes, Deuteromycetes and Zygomycetes), and an action on sludge-dwelling organisms and algae. Examples of such organisms include microorganisms of the following genera: Alternaria, such as Alternaria tenuis; Aspergillus, such as Aspergillus niger; Chaetomium, such as Chaetomium globosum; Coniophora, such as Coniophora puetana; Lentinus, such as Lentinus tigrinus; Penicillium, such as Penicillium glaucum; Polyporus, such as Polyporus versicolor; Aureobasidium such as Aureobasidium pullulans; Sclerophoma such as Sclerophoma pityophila; Trichoderma such as Trichoderma viride; Ophiostoma spp., Ceratocystis spp., Humicolas pp., Petriella spp., Trichurus spp., Coriolus spp., Gloeophyllum spp., Pleurotus spp., Poria spp., Serpula spp. and Tyromyces spp., Cladosporium spp., Paecilomyces spp. Mucor spp., Escherichia such as Escherichia coli; Pseudomonas such as Pseudomonas aeruginosa; Staphylococcus such as Staphylococcus aureus, Candida spp. and Saccharomyces spp., such as Saccharomyces cerevisae.

Seed treatment.

The present invention also includes a method for treating seeds.

Another aspect of the present invention relates in particular to seeds (in a dormant state, primed, germinated or even with sprouted roots and leaves) treated with a combination of compounds according to the invention or a composition containing such a combination. The seeds according to the invention are used in methods for protecting seeds and seedlings of plants from phytopathogenic harmful fungi. In accordance with these methods, seeds treated with a combination of compounds according to the invention or a composition containing it are used.

The combination of compounds according to the invention and compositions containing such a combination can also be used for treating seeds and seedlings. Most damage to agricultural crops by harmful organisms is caused by contamination of seeds before sowing in the soil or after germination of plants. This phase is particularly critical, since during this period the roots and shoots of the growing plant are most susceptible to damage, and even minor damage can cause the death of the plant. Therefore, it is especially important to protect seeds and germinating plants with suitable compositions.

It is also desirable to optimize the amount of active ingredient used in such a way as to ensure the most effective protection of seeds and germinating plants and shoots from attack by phytopathogenic fungi, but without damaging the plant itself with the active ingredient used. In order for the treatment methods to achieve optimal protection of seeds and germinating plants with a minimum consumption of protective compositions, in particular, it is necessary to take into account the natural phenotypes of transgenic plants.

Thus, the present invention also relates to a method for protecting seeds and germinating plants and seedlings from attack by animal pests and/or phytopathogenic harmful microorganisms by treating the seeds with a combination or composition according to the invention. The invention also relates to the use of combinations or compositions according to the invention for treating seeds in order to protect seeds, germinating plants or emerged seedlings from animal pests and/or phytopathogenic microorganisms. The invention further relates to seeds that have been treated with a combination or composition according to the invention for protection against animal pests and/or phytopathogenic microorganisms.

- 22 047972

One of the advantages of the present invention is that the treatment of seeds with such compositions provides protection against animal pests and/or phytopathogenic harmful microorganisms not only for the seeds themselves, but also for the plants grown from them after emergence. In this case, direct treatment of the crop during sowing and immediately after it can protect the plants. Seeds can also be treated before sowing. It is also considered preferable that the combination of active ingredients or the composition according to the invention, in particular, can be used to treat transgenic seeds, in which case the plant grown from such a seed is capable of expressing a protein that counteracts animal pests, herbicide damage and abiotic stress. Treatment of such seeds with active ingredients or compositions according to the invention, for example an insecticidal protein, can ensure counteraction against certain pests.

The combination of compounds according to the invention and compositions containing such a combination can be used to protect the seeds of any plant variety used in agriculture, in greenhouse cultivation, in the forest or used in the field of plant growing or horticulture. More precisely, these can be seeds of cereal crops (such as wheat, barley, rye, millet and oats), oilseed rape, corn, cotton, soybeans, rice, potatoes, sunflowers, beans, coffee, beets (for example, sugar beets and fodder beets), peanuts, vegetables (such as tomatoes, cucumbers, onions and lettuce), turf and ornamental crops. Of particular importance is the treatment of seeds of wheat, soybeans, oilseed rape, corn and rice.

As already noted, the treatment of transgenic seeds with the combinations of compounds or compositions according to the invention is of particular importance. This applies to plant seeds which contain at least one heterologous gene which provides for the expression of a polypeptide or protein with special insecticidal properties. In transgenic seeds, such heterologous genes can originate, for example, from microorganisms of the genera Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium. Such heterologous genes preferably originate from the genus Bacillus, in which case the gene product is effective against the European corn moth and/or the western corn rootworm. Particularly preferred are heterologous genes originating from Bacillus thuringiensis.

In the context of the present invention, the composition or combination according to the invention is applied only to the seeds or in a suitable formulation. Preferably, the seeds are sufficiently hard to prevent damage during processing. Typically, the seed processing is carried out at any time between harvesting and sowing and some time after sowing. Typically, seeds are used that have been separated from the plant and from which the cob, husk, stalk, shell, hair or pulp of the fruit have been removed. For example, seeds can be used that have been collected, cleaned and dried so that the moisture content is less than 15% by weight. Alternatively, it is also possible to use seeds that, after drying, have been, for example, treated with water and then dried again, or seeds immediately after their priming, seeds that are stored in a primed state, or pre-germinated seeds, or seeds sown on brooder trays, film or paper.

During seed treatment, special attention should be paid to the fact that the amount of the combination or composition according to the invention applied to the seeds and/or the amount of additional additives is selected in such a way as not to harm the process of seed germination and the plant itself. This should be ensured, especially in the case of using active ingredients that may have a phytotoxic effect at certain dosages.

The combination of compounds according to the invention and the compositions containing such a combination can be used directly, i.e. when they do not contain any other components, without dilution. In general, it is preferable to apply the compositions to the seeds in the form of the required formulation. Suitable formulations and methods for treating seeds are known to those skilled in the art. The combinations of compounds according to the invention can be prepared into conventional formulations suitable for application to seeds, such as solutions, emulsions, suspensions, powders, foam preparations, liquid solutions or in combination with other compositions for coating seeds, such as film-forming materials, pelleting materials, fine-grained iron or other metal powders, granules, materials for application to inactivated seeds, as well as preparations for ULV.

These preparations are prepared by conventional methods by mixing the active ingredients or their combinations with conventional additives, such as conventional fillers, as well as solvents or diluents, colorants, wetting agents, dispersants, emulsifiers, antifoaming agents, preservatives, auxiliary thickeners, binders, gibberellins, and water.

Suitable colorants that may be present in the seed coating formulations useful in accordance with the invention are any colorants that may normally be used for such purposes. Other pigments that are sparingly soluble in water or colorants that are soluble in water may also be used. Examples of colorants include those known under the names Rhodamine B, C.I. pigment red 112, and C.I. soluble

- 23 047972 red body 1.

Suitable wetting agents that may be present in the seed application formulations useful according to the invention are any wetting agents that may be commonly used in the manufacture of formulations containing active agrochemical ingredients. Preferably suitable are alkyl naphthalene sulphonates such as diisopropyl or diisobutyl naphthalene sulphonates.

Suitable dispersants or emulsifiers that may be present in the seed application formulations useful according to the invention are any nonionic, anionic and cationic dispersants that may normally be used in the manufacture of formulations containing active agrochemical ingredients. The use of nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants is preferred. Suitable nonionic dispersants include, in particular, ethylene oxide/propylene oxide block copolymers, alkylphenol polyglycol ether and tris-trirylylphenol polyglycol ether, as well as phosphated and sulfated derivatives thereof. Suitable anionic dispersants are, in particular, lignosulphates, polyacrylic acid salts and formaldehyde condensates with aryl sulphonate.

Antifoaming agents that may be present in the seed application formulations useful according to the invention are any foam inhibitors that may normally be used in the manufacture of formulations containing active agrochemical ingredients. Silicone antifoaming agents and magnesium stearate are preferred.

Preservatives that may be present in the seed application preparations useful according to the invention are any substances that may normally be used for such purposes in the manufacture of agrochemical compositions. Examples of such substances include dichlorphen and benzyl alcohol semiformal.

Auxiliary thickeners that may be present in the seed application preparations useful according to the invention are any substances that may normally be used for such purposes in the manufacture of agrochemical compositions. Preferred examples include cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.

Binders that may be present in the seed application preparations useful in the present invention are any substances that may normally be used for such purposes in the manufacture of seed application products. Preferred examples of such substances include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.

The seed application formulations that are applicable according to the invention can be used to treat a wide range of different types of seeds, either directly or after preliminary dilution with water. For example, concentrates and formulations obtained from them by dilution with water can be used to apply to seeds of cereal crops such as wheat, barley, rye, oats and triticale, as well as to seeds of corn, soybeans, rice, oilseed rape, peas, beans, cotton, sunflower and beets, as well as to various types of seeds of various vegetables. The formulations that are applicable according to the invention, or preparations obtained by dilution thereof, can also be used with seeds of transgenic plants. In this case, additional synergistic effects can also occur when interacting with substances that are formed as a result of expression.

For treating seeds with seed dressing compositions that can be used in accordance with the present invention or with preparations obtained from them by adding water, all mixing devices that are usually used for application to seeds can be used. In particular, during the application procedure to seeds, these seeds are placed in a mixing device, a certain, necessary amount of preparations is added to them, separately or after dilution with water, and the entire volume is mixed until all preparations are uniformly distributed on the seeds. If necessary, this is followed by a drying operation.

The application rate of the preparations usable according to the present invention can vary within a relatively wide range. It depends on the specific content of active ingredients in the preparation form, as well as on the seeds. The application rate of each individual active ingredient is usually from 0.001 to 15 g per 1 kg of seeds, preferably from 0.01 to 5 g per 1 kg of seeds.

GMO.

As already stated above, all plants and parts thereof can be treated according to the present invention. In a preferred embodiment of the invention, plants and parts thereof of varieties and species occurring in the wild or bred by conventional biological methods, such as crossing or protoplast synthesis, are treated. According to another preferred embodiment, transgenic plants obtained by genetic engineering methods, if appropriate in combination with conventional methods (genetically modified organisms), and parts of such plants are treated. Explanation of the terms parts, or plant parts, or

- 24 047972 plant parts have been given above. More preferably, in accordance with the present invention, plants of varieties that are commercially available or used are processed. The term plant varieties means plants with new properties (characteristics) that have been obtained by conventional breeding methods, mutagenesis or using recombinant DNA technology. These may be varieties, varieties, bio- or genotypes.

The method of treatment according to the invention can be used for the treatment of genetically modified organisms (GMO), such as plants or seeds. Genetically modified plants (or transgenic plants) are plants in which a heterologous gene is stably integrated into the genome. The expression heterologous gene essentially means a gene that is created or assembled outside the plant and which, when introduced into the nuclear, chloroplast or mitochondrial genome, produces a transformed plant with new or improved agronomic or other properties, due to the expression of a target protein or polypeptide or due to the negative regulation or silencing of another (other) gene (genes) that are present in the plant (using, for example, antisense technology, cosuppressor technology, or RNA interference (RNAi) technology, or microRNA (miRNA) technology). A heterologous gene that is localized in the genome is also called a transgene. A transgene that is determined by a specific location in the plant genome is called a transformation or transgenic object.

Plants and plant varieties which are preferably subjected to treatment according to the invention include all plants having genetic material which imparts particularly advantageous useful characteristics to these plants (obtained by breeding and/or plant biotechnology methods).

Plants and plant varieties which are also preferably subjected to the treatment according to the invention are such plants which are resistant to one or more biotic stress factors, i.e. said plants exhibit increased resistance to animal pests and microbial pests, such as nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses and/or viroids.

Plants and plant varieties that can also be treated according to the invention are such plants that are resistant to one or more abiotic stress factors. Abiotic stress conditions include, for example, drought, high and low temperatures, osmotic stress, flooding, increased soil salinity, increased presence of minerals in the soil, presence of extraordinary amounts of ozone, excess light, lack of nitrogen or phosphorus nutrients, lack of shading.

Plants and plant varieties that can also be processed according to the invention are such plants that have improved yield characteristics. Improved yield of said plants can be the result of, for example, improved physiological, growth and development indicators of the plant, such as water use efficiency, water retention efficiency, improved nitrogen assimilation, enhanced carbon assimilation, improved photosynthesis, increased germination and accelerated maturation. Yield may also be affected by improved plant organization (under stress and non-stress conditions) including, but not limited to, early flowering, control of flowering to produce hybrid seed, germination, plant size, number and spacing of internodes, root growth, seed size, fruit size, pod size, number of pods or spikes, number of seeds per pod or spike, seed weight, increased percentage of filled seeds, reduced seed shattering, reduced pod cracking, and lodging resistance. Other yield characteristics include seed composition such as carbohydrate content and composition such as cottonseed or starch, protein content, oil content and fat composition, nutritional value, reduced non-nutritive matter, improved processability, and better storage stability.

Plants that can be treated according to the invention are hybrid plants that already exhibit traits of heterosis or hybrid vigor, which results in generally improved yield, vigor, vigor and resistance to biotic and abiotic stress factors.

Plants or plant varieties (obtained by plant biotechnology methods, such as genetic engineering) that can be treated according to the invention are herbicide-resistant plants, i.e. plants that have resistance to one or more specific herbicides. Such plants, which can be obtained by genetic transformation or plant breeding, contain a mutation that confers such resistance to herbicides.

Plants or plant varieties (obtained by plant biotechnology methods, such as genetic engineering), which can also be treated according to the invention, are transgenic insect-resistant plants, i.e. plants that have been given resistance to attack by certain target insects. Such plants, which can be obtained by genetic transformation or plant breeding, contain a mutation that confers such insect resistance.

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Plants or plant varieties (obtained by plant biotechnology methods, such as genetic engineering), which can also be processed according to the invention, are resistant to abiotic stress factors. Such plants, which can be obtained by genetic transformation or plant breeding, contain a mutation that imparts such resistance to stress.

Plants or plant varieties (obtained by plant biotechnology methods, such as genetic engineering), which can also be processed according to the invention, exhibit altered quantitative and qualitative characteristics and/or storage stability characteristics of the harvested crop product, and/or altered characteristics of certain ingredients of the harvested crop product.

Plants or plant varieties (which may be obtained by plant biotechnology methods, such as genetic engineering), which may also be processed according to the invention, are plants, such as cotton plants, with altered fibre characteristics. Such plants, which may be obtained by genetic transformation or plant selection, contain a mutation that imparts such altered properties to the fibre.

Plants or plant varieties (which may be obtained by plant biotechnology methods such as genetic engineering) which may also be processed according to the invention are plants such as oilseed rape and related Brassica plants with altered oil profile properties. Such plants, which may be obtained by genetic transformation or plant breeding, contain a mutation which imparts such altered oil profile properties.

Plants or plant varieties (which may be obtained by plant biotechnology methods such as genetic engineering) which may also be treated according to the invention are plants, such as oilseed rape and related Brassica plants, with altered seed shattering characteristics. Such plants, which may be obtained by genetic transformation or plant breeding, contain a mutation conferring such altered seed shattering characteristics and include plants, such as oilseed rape, with delayed or reduced seed shattering.

Plants or plant varieties (which may be obtained by plant biotechnology methods such as genetic engineering) that may also be treated according to the invention are plants, such as tobacco, with altered protein post-translational modification profiles.

Application.

When using the combinations according to the invention and compositions containing such combinations as fungicides, the application rate can vary within a relatively wide range, depending on the type of application.

Application rates:

in the case of treatment of plant parts, such as leaves: 0.1-10000 g/ha, preferably 10-1000 g/ha, more preferably 50-300 g/ha (in the case of treatment by watering or irrigation, it is possible to reduce the application rate even further, especially if inert substrates such as mineral wool or perlite are used);

in case of seed treatment: 0.1-200 g per 100 kg of seeds, preferably 1-150 g per 100 kg of seeds, more preferably 2.5-25 g per 100 kg of seeds, even more preferably 2.5-12.5 g per 100 kg of seeds;

in the case of soil treatment: 0.1-10000 g/ha, preferably 1-5000 g/ha, wherein the amounts given refer to the total amount of active ingredient in the respective combination or composition.

The indicated dosages are given solely as an example and do not limit the objectives of the invention.

The present invention is illustrated by the following examples. However, the invention is not limited to these examples.

Examples

The improved fungicidal activity of the combinations of active compounds according to the invention is shown in the following examples. While the individual active compounds show weakness in fungicidal activity, the combinations show activity that is superior in its properties to a simple combination of activities.

A synergistic effect of fungicides is always present when the fungicidal activity of combinations of active compounds exceeds the sum of the activities of the active compounds when applied separately. The expected activity of a given combination of two active compounds can be calculated as follows (cf. Colby, S.R., Calculating Synergistic and Antagonistic Responses of Herbicide Combinations, Weeds 1967, 15, 20-22):

If

X - efficiency when treatment with active compound A is carried out at a dosage of m ppm (or g/ha),

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Y is the efficiency when treatment with active compound B is carried out at a dosage of n ppm (or g/ha), and

E - efficiency, when treatment with active compounds A and B is carried out at a dosage of m and n ppm (or g/ha), respectively, then y · Y

E = Y + Y- -100

For ternary mixtures, the following Colby equation is obtained:

If

X - efficiency when treatment with active compound A is carried out at a dosage of m ppm (or g/ha),

Y - efficiency when treatment with active compound B is carried out at a dosage of n ppm (or g/ha),

Y - efficiency when treatment with active compound C is carried out at a dosage of about ppm (or g/ha), and

E - efficiency, when treatment with active compounds A, B and C is carried out at doses of m, n and o ppm (or g/ha), respectively, then _{g ν ν Ύ} Χ·Υ Χ·Ζ Υ·Ζ Χ-Υ-Ζ

100 100 100 100-100

The degree of effectiveness is expressed as a percentage. 0% means the effectiveness corresponds to the control group of plants, and 100% effectiveness means that the disease is not observed.

If the actual activity exceeds the calculated value, the activity of the combination is superadditive, i.e. there is a synergistic effect. In this case, the actually observed effectiveness should be higher than the value of the predicted effectiveness (E), the calculation of which is made in accordance with the above formula.

Another way of demonstrating the synergistic effect is that described by Tammes (cf. Isoboles, a graphic representation of synergism in pesticides in Neth. J. Plant Path., 1964, 70, 73-80).

Example A. In vitro study, fungal microorganisms.

The wells of 96-well microtiter plates were filled with 30 μl of the preparation of the compound under study or a combination of compounds in methanol + alkyl aryl polyglycol ether emulsifier. The solvent was then evaporated in a cap. At the next stage, 200 μl of liquid nutrient medium were added to each well, into which the appropriate concentration of spores or mycelial suspension of the fungus under study was introduced.

Using a photometer, the optical density is measured in all wells at a wavelength of 620 nm.

The microtitre plates were incubated for 3 to 7 days at 20°C and 85% relative humidity. After incubation, growth inhibition was determined photometrically. Efficiency was calculated relative to a control group of untreated plants; an efficiency of 0% meant a growth of the fungus corresponding to the control group of untreated plants, while an efficiency of 100% meant that no growth of the fungus was detected when measured.

The tables below clearly demonstrate that the observed activity of the combination of active compounds according to the invention exceeds the calculated activity, i.e. a synergistic effect is present.

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Table A in vitro - Tests using Botrytis cinerea

(I-l) (ppm) isoflucip ram (ppm) (2.005) fluopyram (ppm) (2.060) cyclobuterilfluram (ppm) ratio efficiency % Expected value calculated by the Colby method % 0.1 0 0.04 0 20 99 0.8 86 0.16 68 0.1 0.04 20 1:0.4:200 99 99 0.1 0.04 0.8 1:0.4:8 90 86 0.1 0.04 0.16 1:0.4:1.6 71 68 0.5 9 0.1 0 0.02 9 0.2 85 0.04 0 0.008 49 5 30 0.5 0.2 5 1:0.4:10 98 91 0.1 0.04 5 1:0.4:50 98 30 0.02 0.008 5 1:0.4:250 99 68

Table B in vitro tests using Cercospora beticola

(1-1) (ppm) isoflucipr m (ppm) (2.019) pidiflumeto fen (ppm) ratio efficiency % Expected value calculated by the Colby method % 2.5 99 0.5 74 0.1 36 0.02 50 1 88 0.2 0 0.04 30 0.008 20 1 91 2.5 1 1 1:0.4:0.4 100 100 0.5 0.2 1 1:0.4:2 98 98 0.1 0.04 1 1:0.4:10 97 96 0.02 0.008 1 1:0.4:50 100 96

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Table C in vitro - Tests using Diaporthe citri

(I-l) (ppm) isoflucip ram (ppm) (2.005) fluopyram (ppm) (2.019) pidiflume tofen (ppm) ratio efficiency % Expected value calculated by the Colby method % 2.5 99 0.02 0 1 0 0.008 5 20 12 4 0 2.5 1 20 1:0.4:8 100 99 2.5 1 4 1:0.4:1.6 99 99 0.02 0.008 20 1:0.4:1000 23 16 0.02 0.008 4 1:0.4:200 10 5 2.5 99 0.5 90 0.02 0 1 9 0.2 15 0.008 0 0.2 0 2.5 1 0.2 1:0.4:0.08 99 99 0.5 0.2 0.2 1:0.4:0.4 94 91 0.02 0.008 0.2 1:0.4:10 0 1

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Table D in vitro - Tests using Fusarium culmorum

(1-1) (ppm) isofluci pram (ppm) (2.005) fluopyr m (ppm) (2.060) cyclobutyl riflur m (ppm) (2.019) pidiflu metofen (ppm) ratio effects % Expected value calculated by the Colby method % 0.1 9 0.02 11 0.04 4 0.008 2 20 23 4 6 0.1 0.04 20 1:0.4:200 47 33 0.1 0.04 4 1:0.4:40 40 18 0.02 0.008 20 1:0.4:100 0 56 33 0.02 0.008 4 1:0.4:200 26 18 0.5 15 0.1 9 0.02 11 0.2 0 0.04 4 0.008 2 0.2 44 0.5 0.2 0.2 1:0.4:0.4 63 53 0.1 0.04 0.2 1:0.4:2 54 51 0.02 0.008 0.2 1:0.4:10 47 52 0.5 0 0.1 0 0.2 11 0.04 0 0.2 38 0.04 34 0.008 7 0.5 0.2 0.2 1:0.4:0.4 50 44 0.5 0.2 0.04 1:0.4:0.08 40 41 0.5 0.2 0.008 1:0.4:0.01 6 21 17 0.1 0.04 0.2 1:0.4:2 42 38 0.1 0.04 0.04 1:0.4:0.4 43 34 0.1 0.04 0.008 1:0.4:0.08 17 7

Table E in vitro - Tests using Parastagonosyora nodorum

(1-1) (ppm) isofluci pram (ppm) (2.019) pidiflumeto fen (ppm) ratio efficiency % Expected value calculated by the Colby method % 2.5 100 0.1 87 0.02 0 1 82 0.04 49 0.008 69 1 86 2.5 1 1 1:0.4:0.4 100 100 0.1 0.04 1 1:0.4:10 100 99 0.02 0.008 1 1:0.4:50 100 96

Claims (6)

1. A combination of active compounds for combating harmful microorganisms in the field of plant protection and material protection, containing: (A) as compound (A) methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoate, - 30 047972 (B) as compound (B) isoflucipram, (C) as compound (C) at least one active compound selected from (2.005) fluopyram, (2.019) pydiflumetofen and (2.060) cyclobutrifluram. 2. A combination of active compounds according to claim 1, characterized in that the combination of compounds is selected from the group (T1-1D) consisting of the following mixtures: methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoate + isoflucipram + (2.005) fluopyram; methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoate + isoflucipram + (2.019) pidiflumetofen; methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoate + isoflucipram + (2.060) cyclobutrifluram. 3. A combination of active compounds according to one of paragraphs 1, 2, characterized in that the mass ratio of compound (A) and compound (B) is from 1000:1 to 1:1000. 4. A combination of active compounds according to one of paragraphs 1-3, characterized in that the mass ratio of compound (A) and compound (C) is from 1000:1 to 1:1000. 5. A combination of active compounds according to one of claims 1-4, additionally containing an active compound selected from insecticides and plant growth regulators. 6. A composition for combating harmful microorganisms in the field of plant protection and material protection, characterized by containing a combination of active compounds according to one of claims 1 to 5, in addition to at least one carrier and/or surfactant.