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

Abstract

NOT VISIBLE DUE TO STATUS OF PATENT

Description

Emulsifiable concentrates comprising methyl 2-|2-chloro-4-(4-chloronhenoxy)nhenyl|-2-hvdroxy-3-(1,2,4-triazol-l-vDpropanoateThe present invention relates to emulsifiable concentrates of methyl 2-[2-chloro-4-(4- chlorophenoxy)phenyl]-2-hydroxy-3-(l,2,4-triazol-l-yl)propanoate, a process for the preparation of these formulations and their use for controlling harmful microorganisms in crop protection and in the protection of materials, especially for control of phytopathogenic fungi.Methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl] -2-hydroxy-3 -( 1 ,2,4-triazol- 1 -yl)propanoate, synthesis thereof and its fungicidal efficacy is known from WO 2019 / 093522 Al . WO 2019 / 093522 Al also discloses various formulations comprising methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(l,2,4- triazol-l-yl)propanoate, as well as active compound combinations comprising besides methyl 2-[2-chloro- 4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(l,2,4-triazol-l-yl)propanoate at least one further active ingredient, in particular a further fungicide.An important agricultural formulation for the delivery of active ingredients of low or no solubility in water, like methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(l,2,4-triazol-l-yl)propanoate, is an emulsifiable concentrate. This formulation type is generally abbreviated as EC. EC formulations are based on non-water-soluble solvents / components, which upon addition to water generate an emulsion of the nonwater soluble components in the aqueous medium. This emulsion is the actual spray solution that is applied to the locus, e.g. a field or a part thereof, that is in need of treatment. The generation of the emulsion usually happens spontaneously. In some cases, however, some agitation, e.g. stirring, is required to provide the desired homogeneous distribution of the active ingredient(s) in the spray solution.WO 2019 / 093522 Al discloses in paragraph

[0323] , preparation example 2, an emulsifiable concentrate of methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(l,2,4-triazol-l-yl)propanoate, namely an EC50 formulation. The number next to the formulation type, in this case EC, indicates the amount of a.i. (a.i. = active ingredient) in the formulation in g / 1, i.e. the EC50 formulation disclosed in WO 2019 / 093522 Al comprises 50 g / 1 of the respective a.i. methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3- (l,2,4-triazol-l-yl)propanoate. Besides the a.i. the EC50 formulation comprises various emulsifiers as well as the solvents N,N-dimethyloctanamide / N,N-dimethyldecanamide and soybean fatty acid methyl ester.A refined EC50 formulation of methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(l,2,4-triazol- l-yl)propanoate is known from Research Disclosure RD707009, published digitally on 26 January 2023 and in the March 2023 Research Disclosure paper journal. Said EC50 formulation comprises the a.i., various emulsifiers, and the solvents N,N-dimethyloctanamide / N,N-dimethyldecanamide and solvent naphtha.Albeit the known emulsifiable concentrates of methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy- 3-(l,2,4-triazol-l-yl)propanoate are stable and readily provide the desired spray solutions upon addition to water, they show certain disadvantages. To ensure reliable efficacy, a sufficient amount of a.i. needs to be applied to a given area. It is, however, highly desirable to only apply low amounts of spray solution, since handling of lower volumes involves less efforts, e.g. in generating, transporting and applying the spray solutions. Hence, a high concentration of a.i. in the spray solution is desirable. To arrive at such high a.i. concentration in the spray solution starting from the known EC50 formulations, the mixing ratio of emulsifiable concentrate to water needs to be comparatively high. Unfortunately, respective concentrated spray solutions based on the known emulsifiable concentrates proved to attack sealing rings in conventional spraying equipment.Hence, there is need for emulsifiable concentrates of methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2- hydroxy-3-(l,2,4-triazol-l-yl)propanoate that allow for generation of spray solutions comprising a high a.i. concentration that are less aggressive to sealing rings. It is an object of the present invention to provide such emulsifiable concentrates.The object described above is achieved by the emulsifiable concentrates according to the invention comprising methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl] -2-hydroxy-3 -( 1 ,2,4-triazol- 1 -yljpropanoate and N-(n-butyl)-2 -pyrrolidone, the latter in the following simply referred to as N-butyl-pyrrolidone.Accordingly, the present invention provides compositions comprising(A) methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl] -2 -hydroxy-3 -( 1 ,2,4-triazol- 1 -yljpropanoate, and(B) N-butyl-pyrrolidone.US 2020 / 323206 Al discloses emulsion concentrates of various active agrochemical ingredients comprising certain N-substituted pyrrolidones, preferably N-butyl-pyrrolidone, but does not mention the specific a.i. methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(l,2,4-triazol-l-yl)propanoate. The N- substituted pyrrolidones are said to have good dissolving properties and to enable a high loading of crop protection compositions with active agrochemical ingredient, serving as polar aprotic solvents in particular (see paragraph

[0018] ), or as cosolvents in solvent-containing formulations (see paragraph

[0021] ). The N- substituted pyrrolidones are furthermore said to promote the penetration of active agrochemical ingredients into plants or into non-plant harmful organisms (see paragraph

[0001] ). US 2020 / 323206 Al is silent about the problem of ring swelling. Ring swelling is caused by penetration of components of the formulation into the ring material. Conventional sealing rings are made from rubber, i.e. plant-derived material. Hence, using a substance like N-(n-butyl)-2 -pyrrolidone that is said to be particularly potent to promote penetration into plants or into non-plant harmful organisms is highly counterintuitive, if one aims to avoid ring swelling.WO 2023 / 208447 Al strives for provision of solvents suitable for use in emulsifiable concentrate formulations and emulsion-in-water formulations, which combine low phytotoxicity and generally benign (e.g. non-irritant) properties with high solubility for a range of commonly employed agrochemical active ingredients (page 2, lines 13-16). WO 2023 / 208447 Al mentions methyl 2-[2-chloro-4-(4- chlorophenoxy)phenyl]-2-hydroxy-3-(l,2,4-triazol-l-yl)propanoate amongst an exhaustive list of active ingredients. Rather than N-substituted pyrrolidones, WO 2023 / 208447 Al proposes certain benzaldehydederived solvents which are said to be advantageous over usual solvents used in emulsion concentrates. Like US 2020 / 323206 Al, also WO 2023 / 208447 Al is silent about the problem of ring swelling. Hence, neither US 2020 / 323206 Al, nor WO 2023 / 208447 Al address the same technical problem as present invention. Gist of WO 2023 / 208447 Al is addition of certain benzaldehyde-derived solvents to overcome defects of usual solvents for EC formulations, in particular low solubility of many active ingredients. Replacing such solvent by one of those known solvents, like the N-substituted pyrrolidones of US 2020 / 323206 Al, would be contrary to the core of the teaching of WO 2023 / 208447 Al.Surprisingly, presence of N-butyl-pyrrolidone in emulsifiable concentrates of methyl 2-[2-chloro-4-(4- chlorophenoxy)phenyl]-2-hydroxy-3-(l,2,4-triazol-l-yl)propanoate reduces the swelling of sealing rings in contact with spray solutions derived from said EC formulations, even at high concentrations of methyl 2-[2- chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(l,2,4-triazol-l-yl)propanoate in the actual spray solution. Moreover, presence of N-butyl-pyrrolidone allows for high loading of the emulsifiable concentrates with the a.i.. For example EC75 and EC100 formulations can be prepared, if N-butyl-pyrrolidone is present.The compositions according to the invention comprise as active ingredient methyl 2-[2-chloro-4-(4- chlorophenoxy)phenyl]-2-hydroxy-3-(l,2,4-triazol-l-yl)propanoate, which may be present as such or in form of a salt or N-oxide thereof. The salts or N-oxides of methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]- 2 -hydroxy-3 -(1, 2, 4-triazol-l-yl)propanoate also have fungicidal properties.Methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl] -2 -hydroxy-3 -(1, 2, 4-triazol-l-yl)propanoate is depicted by formula (1-1)and is denoted in the following also compound (1-1) or simply (1-1).As apparent from formula (I- 1), compound (1-1) comprises a stereogenic center at the carbon atom bearing the hydroxy group. Hence, methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(l,2,4-triazol-l- yl)propanoate can be present in form of the optical isomers, their racemic or scalemic mixtures (the term "scalemic" denotes a mixture of enantiomers in different proportions), in all proportions. Compound (1-1) may be used in the compositions according to this invention in any of said forms, i.e. (1-1) may be present as methyl (2R)-2-[2-chloro-4-(4-chlorophenoxy)phenyl] -2-hydroxy-3 -( 1 ,2,4-triazol- 1 -yl)propanoate, methyl (2S)-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-(l,2,4-triazol-l- yl)propanoate and methyl (2S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(l,2,4-triazol-l- yl)propanoate, and any scalemic mixture of methyl (2R)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2- hydroxy-3-(l,2,4-triazol-l-yl)propanoate and methyl (2S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2- hydroxy-3-( 1 ,2,4-triazol- 1 -yl)propanoate .The composition comprises methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(l,2,4-triazol-l- yl)propanoate preferably in an amount of 1 to 50 % by weight, more preferably 2 to 50 % by weight, more preferably 3 to 50 % by weight, more preferably 4 to 50 % by weight, more preferably 5 to 50 % by weight, more preferably 5 to 40 % by weight, more preferably 5 to 30 % by weight, more preferably 5 to 25 % by weight, more preferably 5 to 20 % by weight, more preferably 5 to 15 % by weight, more preferably 5 to 14 % by weight, more preferably 5 to 13 % by weight, more preferably 5 to 12 % by weight, more preferably 5 to 11 % by weight, even more preferably 6 to 11 % by weight, and most preferably 7 to 11 % by weight.Unless explicitly stated otherwise, any referral to a percentage by weight given above and below is based on the total weight of the composition according to the invention.The compositions according to the invention further comprise N-(n-butyl)-2 -pyrrolidone.The amount of N-(n-butyl)-2-pyrrolidone is preferably 5 to 99 % by weight, more preferably 6 to 99 % by weight, more preferably 7 to 99 % by weight, more preferably 8 to 99 % by weight, more preferably 9 to 99 % by weight, more preferably 9 to 90 % by weight, more preferably 9 to 80 % by weight, more preferably 9 to 70 % by weight, more preferably 9 to 60 % by weight, even more preferably 9 to 50 % by weight, and most preferably 9 to 40 % by weight.The compositions according to the invention optionally comprise at least one further active ingredient different from compound (1-1). The further active ingredient, if present, can be selected for example from bactericides, acaricides, nematicides, insecticides and fungicides, in order thus to broaden, for example, the activity spectrum or to prevent development of resistance. The further active ingredient is preferably a fungicide, preferably selected from the following groups(1) inhibitors of the ergosterol biosynthesis,(2) inhibitors of the respiratory chain at complex I or II,(3) inhibitors of the respiratory chain at complex III,(4) inhibitors of the mitosis and cell division,(5) compounds capable of having a multisite action,(6) compounds capable of inducing a host defense,(7) inhibitors of the amino acid and / or protein biosynthesis,(8) inhibitors of the ATP production,(9) inhibitors of the cell wall synthesis,(10) inhibitors of the lipid synthesis or transport, or membrane synthesis,(11) inhibitors of the melanine biosynthesis,(12) inhibitors of the nucleic acid synthesis,(13) inhibitors of the signal transduction,(14) compounds capable of acting as uncoupler,(15) other fungicides.More preferably, the further active ingredient is a fungicide selected from1) inhibitors of the ergosterol biosynthesis selected from the group consisting of (1.001) cyproconazole, (1.002) difenoconazole, (1.003) epoxiconazole, (1.004) fenbuconazole, (1.005) fenhexamid, (1.006) fenpropidin, (1.007) fenpropimorph, (1.008) fenpyrazamine, (1.009) Fluoxytioconazole, (1.010) fluquinconazole, (1.011) flutriafol, (1.012) hexaconazole, (1.013) imazalil, (1.014) imazalil sulfate, (1.015) ipconazole, (1.016) ipfentrifluconazole, (1.017) mefentrifluconazole, (1.018) metconazole, (1.019) myclobutanil, (1.020) paclobutrazol, (1.021) penconazole, (1.022) prochloraz, (1.023) propiconazole, (1.024) prothioconazole, (1.025) pyrisoxazole, (1.026) spiroxamine, (1.027) tebuconazole, (1.028) tetraconazole, (1.029) triadimenol, (1.030) tridemorph, (1.031) triticonazole, (1.032) 4-[[6-[(2R)-2-(2,4- difluorophenyl)- 1 , 1 -difluoro-2 -hydroxy-3 -(5 -thioxo-4H- 1 ,2,4-triazol- 1 -yl)propyl] -3 -pyridyl]oxy]benzo- nitrile, (1.033) 4-[[6-[(2S)-2-(2,4-difluorophenyl)-l,l-difluoro-2-hydroxy-3-(5-thioxo-4H-l,2,4-triazol-l- yl)propyl]-3-pyridyl]oxy]benzonitrile, (1.034) (2R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-l- (lH-l,2,4-triazol-I-yl)propan-2-ol, (1.035) (2S)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-l-(lH-I,2,4-triazol-I-yl)propan-2-ol, (1.036) l-({(2R,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-l,3- dioxolan-2-yl}methyl)-lH-l,2,4-triazole, (1.037) l-({(2S,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4- methyl-l,3-dioxolan-2-yl}methyl)-lH-l,2,4-triazole, (1.038) 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)- 3-pyridyl]-I-(I,2,4-triazol-I-yl)propan-2-ol, (1.039) 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3- pyridyl]-I-(I,2,4-triazol-I-yl)propan-2-ol, (1.040) 3-[2-(l-chlorocyclopropyl)-3-(3-chloro-2-fluoro- phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile, (1.044) N'-(2,5-dimethyl-4-(2-methylbenzyl)phenyl)- N-ethyl-N-methylformimidamide, (1.045) N'-(2-chloro-4-(4-cyanobenzyl)-5-methylphenyl)-N-ethyl-N- methylformimidamide, (1.046) N'-(2-chloro-4-(4-methoxybenzyl)-5-methylphenyl)-N-ethyl-N- methylformimidamide, (1.047) N'-(2-chloro-5-methyl-4-phenoxyphenyl)-N-ethyl-N-methylimido- formamide, (1.048) N'-(4-benzyl-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide, (1.049) N'- [2-chloro-4-(2-fhiorophenoxy)-5-methylphenyl]-N-ethyl-N-methylimidoformamide, (1.050) N'-[5-bromo- 6-(2,3-dihydro-IH-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimidoformamide, (1.051) N'- {4-[(4,5-dichloro-I,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide, (1.052) N'- { 5 -bromo-2-methyl-6- [( 1 -propoxypropan-2-yl)oxy]pyridin-3 -yl } -N -ethyl-N -methylimidoformamide, (1.053) N'-{5-bromo-6-[(lR)-l-(3,5-difhrorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N- methylimidoformamide, (1.054) N'-{ 5 -bromo-6-[( 1 S)- 1 -(3,5 -difluorophenyl)ethoxy] -2-methylpyridin-3 - yl}-N-ethyl-N-methylimidoformamide, (1.055) N'-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2- methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.056) N'-{5-bromo-6-[(trans-4- isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.057) N'-{5-bromo- 6-[l-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.058) N- isopropyl-N'-[5 -methoxy-2-methyl-4-(2,2,2-trifluoro- 1 -hydroxy- 1 -phenylethyl)phenyl] -N- methylimidoformamide, (1.059) p-tolylmethyl 4-[(E)-[ethyl(methyl)amino]methyleneamino]-2,5-dimethyl- benzoate and (1.060) N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine;2) inhibitors of the respiratory chain at complex I or II selected from the group consisting of (2.001) benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2.004) carboxin, (2.005) cyclobutrifluram, (2.006) flubeneteram, (2.007) fluindapyr, (2.008) fluopyram, (2.009) flutolanil, (2.010) fluxapyroxad, (2.011) furametpyr, (2.012) inpyrfluxam, (2.013) Isofetamid, (2.014) isoflucypram, (2.015) isopyrazam, (2.016) penflufen, (2.017) penthiopyrad, (2.018) pydiflumetofen, (2.019) pyrapropoyne, (2.020) pyraziflumid, (2.021) sedaxane, (2.022) Thifluzamide (aka trifluzamide), (2.023) 5.8-difhioro-N-|2-(2-fliioro-4-{|4- (trifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazolin-4-amine, (2.024) 5-chloro-N-[2-[l-(4-chloro- phenyl)pyrazol-3-yl]oxyethyl]-6-ethyl-pyrimidin-4-amine, (2.025) N-[2-[l-(4-chlorophenyl)pyrazol-3- yl]oxyethyl]quinazolin-4-amine, (2.026) l-methyl-3-(trifluoromethyl)-N-[2'-(trifluoromethyl)biphenyl-2- yl] - lH-pyrazole-4-carboxamide, (2.027) 2-fluoro-6-(trifhioromethyl)-N-( 1 , 1 ,3-trimethyl-2, 3 -dihydro- 1H- inden-4-yl)benzamide, (2.028) 3-(difhroromethyl)-l-methyl-N-(I,I,3-trimethyl-2,3-dihydro-IH-inden-4- yl)-lH-pyrazole-4-carboxamide, (2.029) 3-(difhroromethyl)-l-methyl-N-[(3S)-I,I,3-trimethyl-2,3-dihydro- lH-inden-4-yl]-lH-pyrazole-4-carboxamide, (2.030) 3-(difhioromethyl)-N-[(3R)-7-fhroro-I,I,3-trimethyl-2,3-dihydro-lH-inden-4-yl]-l-methyl-lH-pyrazole-4-carboxamide, (2.031) 3-(difluoromethyl)-N-[(3S)-7- fluoro-l,l,3-trimethyl-2,3-dihydro-lH-inden-4-yl]-l-methyl-lH-pyrazole-4-carboxamide, (2.032) N- [( 1 R,4S)-9-(dichloromethylene)- 1 ,2,3 ,4-tetrahydro- 1 ,4-methanonaphthalen-5 -yl] -3-(difluoromethyl)- 1 - methyl-lH-pyrazole-4-carboxamide, (2.033) N-[(lS,4R)-9-(dichloromethylene)-l,2,3,4-tetrahydro-l,4- methanonaphthalen-5 -yl] -3-(difluoromethyl)- 1 -methyl- lH-pyrazole-4-carboxamide, (2.034) N-[ 1 -(2,4- dichlorophenyl)- 1 -methoxypropan-2-yl] -3 -(difluoromethyl)- 1 -methyl- lH-pyrazole-4-carboxamide, (2.035) 5 -chloro- 1 ,3 -dimethyl -N-[(3 S)- 1 , 1 ,3-trimethyl-3H-isobenzofuran-4-yl]pyrazole-4-carboxamide, (2.036) 5- chloro-l,3-dimethyl-N-[(3R)-l,l,3-trimethyl-3H-isobenzofuran-4-yl]pyrazole-4-carboxamide, (2.037) N-[2-[(lS)-l,3-dimethylbutyl]phenyl]-5-fluoro-l,3-dimethyl-pyrazole-4-carboxamide, (2.038) N-[2-[(lR)- l,3-dimethylbutyl]phenyl]-5-fluoro-l,3-dimethyl-pyrazole-4-carboxamide, (2.039) 3-(difluoromethyl)-N- methoxy- l-methyl-N-[( 1 S)- 1 -methyl-2-(2,4,6-trichlorophenyl)ethyl]pyrazole-4-carboxamide, (2.040) 3- (difluoromethyl)-N-methoxy-l -methyl -N-[( 1R)- 1 -methyl -2 -(2,4, 6-trichlorophenyl)ethyl]pyrazole-4- carboxamide, (2.041) N-[2-[(lS)-l,3-dimethylbutyl]-3-thienyl]-l-methyl-3-(trifluoromethyl)pyrazole-4- carboxamide, (2.042) N- [2- [( 1 R)- 1 ,3 -dimethylbutyl] -3 -thienyl] - 1 -methyl-3 -(trifluoromethyl)pyrazole-4- carboxamide, (2.043) N-[rac-(lS,2S)-2-(2,4-dichlorophenyl)cyclobutyl]-2-(trifluoromethyl)nicotinamide and (2.044) 2-(difluoromethyl)-N-(3-ethyl-l,l-dimethyl-indan-4-yl)pyridine-3-carboxamide;3) inhibitors of the respiratory chain at complex III selected from the group consisting of (3.001) ametoctradin, (3.002) amisulbrom, (3.003) azoxystrobin, (3.004) coumethoxystrobin, (3.005) coumoxystrobin, (3.006) cyazofamid, (3.007) dimoxystrobin, (3.008) enoxastrobin, (3.009) famoxadone, (3.010) fenamidone, (3.011) fenpicoxamid, (3.012) florylpicoxamid, (3.013) flufenoxystrobin, (3.014) fluoxastrobin, (3.015) kresoxim-methyl, (3.016) mandestrobin, (3.017) metarylpicoxamid, (3.018) metominostrobin, (3.019) metyltetraprole, (3.020) orysastrobin, (3.021) picoxystrobin, (3.022) pyraclostrobin, (3.023) pyrametostrobin, (3.024) pyraoxystrobin, (3.025) pyribencarb, (3.026) trifloxystrobin, (3.027) (2E)-2-{2-[({[(lE)-l-(3-{[(E)-l-fluoro-2-phenylvinyl]oxy}phenyl)ethylidene]- amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.028) (2E,3Z)-5-{[l-(4-chloro-2- fluorophenyl)-lH-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (3.029) (2E,3Z)-5- {[l-(4-chlorophenyl)-lH-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (3.030) (2R)- 2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3.031) (2S)-2-{2-[(2,5- dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3.032) (Z,2E)-5-[l-(2,4- dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, (3.033) methyl (Z)-2-(5- cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2 -enoate, (3.034) methyl (Z)-2-(5-cyclopentyl-2-methyl- phenoxy)-3-methoxy-prop-2-enoate, (3.035) methyl (Z)-3-methoxy-2-[2-methyl-5-(3-propylpyrazol-l- yl)phenoxy]prop-2-enoate, (3.036) methyl (Z)-3-methoxy-2-[2-methyl-5-[3-(trifluoromethyl)pyrazol-l- yl]phenoxy]prop-2 -enoate, (3.037) methyl { 5 -[3 -(2,4-dimethylphenyl)- IH-pyrazol- 1 -yl] -2-methylbenzyl} - carbamate, (3.038) (2E)-2-methoxyimino-N-methyl-2-[3-methyl-2-[[(E)-l-[3-(trifluoromethyl)phenyl]- ethylideneamino]oxymethyl]phenyl]acetamide, (3.039) (2E)-2-[2-[[(E)-l-(3,5-difluorophenyl)ethylidene-amino]oxymethyl]-3-methyl-phenyl]-2-methoxyimino-N-methyl-acetamide, (3.040) [rac-2-(4-bromo-7- fluoro-indol- 1 -yl)- 1 -methyl -propyl] (2 S) -2 - [(3 -hydroxy-4-methoxy-pyridine-2-carbonyl)amino] - propanoate, (3.041) [rac-2-(7-bromo-4-fluoro-indol-l-yl)-l -methyl -propyl] (2S)-2-[(3-acetoxy-4-methoxy- pyridine-2-carbonyl)amino]propanoate, (3.042) [rac-2-(7-bromoindol-l-yl)-l -methyl -propyl] (2S)-2-[(3- hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, (3.043) [rac-2-(3,5-dichloro-2-pyridyl)-l- methyl -propyl] (2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, (3.044) [( 1 S)-l -[ 1 - ( 1 -naphthyl)cyclopropyl] ethyl] (2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate,(3.045) [(lS)-l-[l-(l-naphthyl)cyclopropyl]ethyl] (2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)- amino]propanoate, (3.046) [(lS)-l-[l-(l-naphthyl)cyclopropyl]ethyl] (2S)-2-[[3-(acetoxymethoxy)-4- methoxy-pyridine-2-carbonyl]amino]propanoate, (3.047) [2-[[(lS)-2-[(lRS,2SR)-2-(3,5-dichloro-2- pyridyl)-l-methyl-propoxy]-l-methyl-2-oxo-ethyl]carbamoyl]-4-methoxy-3-pyridyl]oxymethyl 2-methyl- propanoate, (3.048) 2-[cyano-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl- thiazole-4-carboxamide, (3.049) 2-[cyano-(2,6-difluoro-4-pyridyl)amino]-5-methyl-N-spiro[3.4]octan-3- yl-thiazole-4-carboxamide, (3.050) 2-[cyano-(2,6-difluoro-4-pyridyl)amino]-N-hexyl-5-methyl-thiazole-4- carboxamide, (3.051) 2-[acetyl-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl- thiazole-4-carboxamide, (3.052) 2-[(2,6-difluoro-4-pyridyl)-(2-methylpropanoyl)amino]-N-(2,2- dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide, (3.053) 2-[(2,6-difluoro-4-pyridyl)-(2-methoxy- acetyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazole-4-carboxamide and (3.054) N-(3-ethyl-3,5,5- trimethylcyclohexyl)-3-formamido-2 -hydroxybenzamide;4) inhibitors of the mitosis and cell division selected from the group consisting of (4.001) carbendazim, (4.002) diethofencarb, (4.003) ethaboxam, (4.004) fluopicolide, (4.005) fluopimomide, (4.006) metrafenone, (4.007) pencycuron, (4.008) pyridachlometyl, (4.009) pyriofenone (chlazafenone), (4.010) thiabendazole, (4.011) thiophanate-methyl, (4.012) zoxamide, (4.013) 3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)- 6-methylpyridazine, (4.014) 3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluoro- phenyl)pyridazine, (4.015) 4-(2-bromo-4-fluorophenyl)-N-(2,6-difluorophenyl)-l,3-dimethyl-lH-pyrazol- 5-amine, (4.016) 4-(2-bromo-4-fluorophenyl)-N-(2-bromo-6-fluorophenyl)-l,3-dimethyl-lH-pyrazol-5- amine, (4.017) 4-(2-bromo-4-fhiorophenyl)-N-(2-bromophenyl)-l,3-dimethyl-lH-pyrazol-5-amine, (4.018) 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-l,3-dimethyl-lH-pyrazol-5-amine, (4.019) 4-(2- bromo-4-fluorophenyl)-N-(2-chlorophenyl)- 1,3 -dimethyl- lH-pyrazol-5 -amine, (4.020) 4-(2-bromo-4- fluorophenyl)-N-(2-fluorophenyl)-l,3-dimethyl-lH-pyrazol-5-amine, (4.021) 4-(2-chloro-4-fluorophenyl)- N-(2,6-difluorophenyl)-l,3-dimethyl-lH-pyrazol-5-amine, (4.022) 4-(2-chloro-4-fluorophenyl)-N-(2- chloro-6-fluorophenyl)-l,3-dimethyl-lH-pyrazol-5-amine, (4.023) 4-(2-chloro-4-fluorophenyl)-N-(2- chlorophenyl)- 1,3 -dimethyl- IH-pyrazol -5 -amine, (4.024) 4-(2-chloro-4-fluorophenyl)-N-(2-fluorophenyl)- l,3-dimethyl-lH-pyrazol-5-amine, (4.025) 4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6- dimethylpyridazine, (4.026) N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-l,3-dimethyl-lH- pyrazol-5-amine, (4.027) N-(2-bromophenyl)-4-(2-chloro-4-fluorophenyl)-l,3-dimethyl-lH-pyrazol-5-amine and (4.028) N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-l,3-dimethyl-lH-pyrazol- 5 -amine;5) compounds capable to have a multisite action selected from the group consisting of (5.001) Bordeaux mixture, (5.002) captafol, (5.003) captan, (5.004) chlorothalonil, (5.005) copper hydroxide, (5.006) copper naphthenate, (5.007) copper oxide, (5.008) copper oxychloride, (5.009) copper(2+) sulfate, (5.010) dithianon, (5.011) dodine, (5.012) folpet, (5.013) mancozeb, (5.014) maneb, (5.015) metiram, (5.016) metiram zinc, (5.017) oxine -copper, (5.018) propineb, (5.019) sulfur and sulfur preparations including calcium polysulfide, (5.020) thiram, (5.021) zineb, (5.022) ziram and (5.023) 6-ethyl-5,7-dioxo-6,7-dihydro- 5H-pyrrolo[3',4':5,6][l,4]dithiino[2,3-c][l,2]thiazole-3-carbonitrile;6) compounds capable to induce a host defence selected from the group consisting of (6.001) acibenzolar- S-methyl, (6.002) fosetyl-aluminium, (6.003) fosetyl-calcium, (6.004) fosetyl-sodium, (6.005) isotianil, (6.006) phosphorous acid and its salts, (6.007) probenazole and (6.008) tiadinil;7) inhibitors of the amino acid and / or protein biosynthesis selected from the group consisting of (7.001) cyprodinil, (7.002) kasugamycin, (7.003) kasugamycin hydrochloride hydrate, (7.004) oxytetracycline and (7.005) pyrimethanil;8) inhibitors of the ATP production: (8.001) silthiofam;9) inhibitors of the cell wall synthesis selected from the group consisting of (9.001) benthiavalicarb, (9.002) dimethomorph, (9.003) flumorph, (9.004) iprovalicarb, (9.005) mandipropamid, (9.006) pyrimorph, (9.007) valifenalate, (9.008) (2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-l-(morpholin-4-yl)prop-2-en-l- one and (9.009) (2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-l-(morpholin-4-yl)prop-2-en-l-one;10) inhibitors of the lipid synthesis or transport, or membrane synthesis selected from the group consisting of (10.001) fluoxapiprolin, (10.002) natamycin, (10.003) oxathiapiprolin, (10.004) propamocarb, (10.005) propamocarb hydrochloride, (10.006) propamocarb-fosetylate, (10.007) tolclofos-methyl, (10.008) l-(4-{4- [(5R)-5 -(2,6-difluorophenyl)-4,5-dihydro- 1 ,2-oxazol-3 -yl] - 1 ,3-thiazol-2-yl }piperidin- 1 -yl)-2-[5 -methyl-3 - (trifluoromethyl)- IH-pyrazol- l-yl]ethanone, ( 10.009) 1 -(4-{4-[(5 S)-5-(2,6-difluorophenyl)-4,5-dihydro- 1 ,2-oxazol-3 -yl] - 1 ,3-thiazol-2-yl }piperidin- 1 -yl)-2-[5 -methyl-3 -(trifluoromethyl)- IH-pyrazol- 1 - yl]ethanone, (10.010) 2-[3,5-bis(difluoromethyl)-lH-pyrazol-l-yl]-l-[4-(4-{5-[2-(prop-2-yn-l-yloxy)- phenyl]-4,5-dihydro-l,2-oxazol-3-yl}-l,3-thiazol-2-yl)piperidin-l-yl]ethanone, (10.011) 2-[3,5- bis(difluoromethyl)- IH-pyrazol- 1 -yl] - 1 -[4-(4- {5 -[2-chloro-6-(prop-2-yn- 1 -yloxy)phenyl] -4,5-dihydro- 1 ,2- oxazol-3-yl}-l,3-thiazol-2-yl)piperidin-l-yl]ethanone, (10.012) 2-[3,5-bis(difluoromethyl)-lH-pyrazol-l- yl]-l-[4-(4-{5-[2-fluoro-6-(prop-2-yn-l-yloxy)phenyl]-4,5-dihydro-l,2-oxazol-3-yl}-l,3-thiazol-2- yl)piperidin-l-yl]ethanone, (10.013) 2-{(5R)-3-[2-(l-{[3,5-bis(difluoromethyl)-lH-pyrazol-l- yl]acetyl}piperidin-4-yl)- 1 ,3 -thiazol-4-yl] -4,5-dihydro- 1 ,2-oxazol-5 -yl} -3 -chlorophenyl methanesulfonate,(10.014) 2-{(5S)-3-[2-(l-{[3,5-bis(difluoromethyl)-lH-pyrazol-l-yl]acetyl}piperidin-4-yl)-l,3-thiazol-4- yl]-4,5-dihydro-l,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate, (10.015) 2-{3-[2-(l-{[3,5- bis(difluoromethyl)- IH-pyrazol- 1 -yl]acetyl}piperidin-4-yl)- 1 ,3 -thiazol-4-yl] -4,5 -dihydro- 1 ,2-oxazol-5 - yl}phenyl methanesulfonate, (10.016) 3-[2-(l-{[5-methyl-3-(trifhioromethyl)-lH-pyrazol-l- yl]acetyl}piperidin-4-yl)- 1 ,3 -thiazol-4-yl] - 1 ,5 -dihydro-2, 4-benzodioxepin-6-yl methanesulfonate, (10.017) 9-fhioro-3-[2-(l-{[5-methyl-3-(trifhioromethyl)-lH-pyrazol-l-yl]acetyl}piperidin-4-yl)-l,3-thiazol-4-yl]- 1 ,5-dihydro-2,4-benzodioxepin-6-yl methanesulfonate, (10.018) 3 - [2 -( 1 - { [3 ,5 -bis(difluoromethyl)- 1H- pyrazol-l-yl]acetyl}piperidin-4-yl)-l,3-thiazol-4-yl]-l,5-dihydro-2,4-benzodioxepin-6-yl methanesulfonate and (10.019) 3-[2-(l-{[3,5-bis(difhroromethyl)-lH-pyrazol-l-yl]acetyl}piperidin-4-yl)-l,3- thiazol-4-yl]-9-fluoro-l,5-dihydro-2,4-benzodioxepin-6-yl methanesulfonate;11) inhibitors of the melanin biosynthesis selected from the group consisting of (11.001) tolprocarb and (11.002) tricyclazole;12) inhibitors ofthe nucleic acid synthesis selected from the group consisting of (12.001) benalaxyl, (12.002) benalaxyl-M (kiralaxyl), (12.003) metalaxyl and (12.004) metalaxyl-M (mefenoxam);13) inhibitors ofthe signal transduction selected from the group consisting of (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazid, (13.005) quinoxyfen and (13.006) vinclozolin;14) compounds capable to act as an uncoupler selected from the group consisting of (14.001) fluazinam and (14.002) meptyldinocap; and15) further compounds selected from the group consisting of (15.001) abscisic acid, (15.002) aminopyrifen,(15.003) benthiazole, (15.004) bethoxazin, (15.005) capsimycin, (15.006) carvone, (15.007) chinomethionat, (15.008) chloroinconazide, (15.009) cufraneb, (15.010) cyflufenamid, (15.011) cymoxanil, (15.012) cyprosulfamide, (15.013) dipymetitrone, (15.014) D-tagatose, (15.015) flufenoxadiazam, (15.016) flumetylsulforim, (15.017) flutianil, (15.018) ipflufenoquin, (15.019) methyl isothiocyanate, (15.020) mildiomycin, (15.021) nickel dimethyldithiocarbamate, (15.022) nitrothal-isopropyl, (15.023) oxyfenthiin, (15.024) pentachlorophenol and salts, (15.025) picarbutrazox, (15.026) quinofumelin, (15.027) tebufloquin, (15.028) tecloftalam, (15.029) tolnifanide, (15.030) 2-(6-benzylpyridin-2-yl)quinazoline, (15.031) 2-[6-(3- fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline, (15.032) 2-phenylphenol and salts, (15.033) 4- amino-5-fluoropyrimidin-2-ol (tautomeric form: 4-amino-5-fluoropyrimidin-2(lH)-one), (15.034) 4-oxo-4- [(2-phenylethyl)amino]butanoic acid, (15.035) 5-amino-l,3,4-thiadiazole-2-thiol, (15.036) 5-chloro-N'- phenyl-N'-(prop-2-yn- 1 -yl)thiophene-2-sulfonohydrazide, (15.037) 5 -fluoro-2-[(4- fluorobenzyl)oxy]pyrimidin-4-amine, (15.038) 5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidin-4-amine, (15.039) but-3-yn-l-yl {6-[({[(Z)-(l-methyl-lH-tetrazol-5- yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate, (15.040) ethyl (2Z)-3-amino-2-cyano-3- phenylacrylate, (15.041) methyl 2-[acetyl-[2-ethylsulfonyl-4-(trifluoromethyl)benzoyl]amino]-5-(trifluoromethoxy)benzoate, (15.042) N-acetyl-N-[2-bromo-4-(trifluoromethoxy)phenyl]-2-ethylsulfonyl- 4-(trifluoromethyl)benzamide, (15.043) phenazine- 1 -carboxylic acid, (15.044) propyl 3,4,5- trihydroxybenzoate, (15.045) quinolin-8-ol, (15.046) quinolin-8-ol sulfate (2:1), (15.047) (2R)-2-benzyl-N- (8-fluoro-2-methyl-3-quinolyl)-2,4-dimethyl-pentanamide, (15.048) (2S)-2-benzyl-N-(8-fluoro-2-methyl- 3-quinolyl)-2,4-dimethyl-pentanamide, (15.049) l-(4,5-dimethyl-lH-benzimidazol-l-yl)-4,4-difluoro-3,3- dimethyl-3,4-dihydroisoquinoline, (15.050) l-(4,5-dimethylbenzimidazol-l-yl)-4,4,5-trifluoro-3,3- dimethyl-isoquinoline, (15.051) l-(5-(fluoromethyl)-6-methyl-pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4- dihydroisoquinoline, (15.052) l-(5,6-dimethylpyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4- dihydroisoquinoline, ( 15.053) 1 -(6-(difluoromethyl)-5 -methoxy-pyridin-3 -yl)-4,4-difluoro-3 ,3-dimethyl- 3,4-dihydroisoquinoline, (15.054) l-(6-(difluoromethyl)-5-methyl-pyridin-3-yl)-4,4-difluoro-3,3-dimethyl- 3,4-dihydroisoquinoline, (15.055) 4,4-difluoro-3,3-dimethyl-l-(7-methylpyrazolo[l,5-a]pyridin-3-yl)- isoquinoline, (15.056) 1 -(6,7-dimethylpyrazolo[ 1 ,5-a]pyridin-3-yl)-4,4,5-trifluoro-3,3-dimethyl- isoquinoline, (15.057) l-(6,7-dimethylpyrazolo[l,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4- dihydroisoquinoline, ( 15.058) 2-{2-fluoro-6-[(8-fluoro-2-methylquinolin-3-yl)oxy]phenyl}propan-2-ol, (15.059) 3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-l-yl)quinoline, (15.060) 3-(4,4-difluoro- 3,3-dimethyl-3,4-dihydroisoquinolin-l-yl)-8-fluoroquinoline, (15.061) 3-(4,4-difluoro-5,5-dimethyl-4,5- dihydrothieno[2,3-c]pyridin-7-yl)quinoline, (15.062) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydro- isoquinolin- 1 -yl)quinoline, ( 15.063) 4,4-difluoro-3,3 -dimethyl- 1 -(4-methylbenzimidazol- 1 -yl)isoquinoline, (15.064) 4,4-difluoro-3,3-dimethyl-l-(6-methylpyrazolo[l,5-a]pyridin-3-yl)isoquinoline, (15.065) 5- bromo-l-(5,6-dimethylpyridin-3-yl)-3,3-dimethyl-3,4-dihydroisoquinoline, (15.066) 7,8-difluoro-N-[rac-l- benzyl-l,3-dimethyl-butyl]quinoline-3-carboxamide, (15.067) 8-fluoro-3-(5-fluoro-3,3,4,4-tetramethyl-3,4- dihydroisoquinolin-l-yl)-quinoline, (15.068) 8-fluoro-3-(5-fluoro-3,3-dimethyl-3,4-dihydroisoquinolin-l- yl)-quinoline, (15.069) 8-fluoro-N-(4,4,4-trifluoro-2-methyl-l-phenylbutan-2-yl)quinoline-3-carboxamide, (15.070) 8-fluoro-N-[(lR)-l-[(3-fluorophenyl)methyl]-l,3-dimethyl-butyl]quinoline-3-carboxamide,(15.071) 8-fluoro-N-[( 1 S)- l-[(3-fluorophenyl)methyl]-l ,3-dimethyl-butyl]quinoline-3-carboxamide,( 15.072) 8-fluoro-N-[(2S)-4,4,4-trifluoro-2-methyl- l-phenylbutan-2-yl]quinoline-3-carboxamide, ( 15.073) 8-fluoro-N-[rac-l-[(3-fluorophenyl)methyl]-l,3-dimethyl-butyl]quinoline-3-carboxamide, (15.074) 9- fluoro-2,2-dimethyl-5 -(quinolin-3 -yl)-2,3 -dihydro- 1 ,4-benzoxazepine, ( 15.075) N-(2,4-dimethyl- 1 - phenylpentan-2-yl)-8-fluoroquinoline-3 -carboxamide, ( 15.076) N-[( 1 R)- 1 -benzyl- 1 ,3 -dimethyl -butyl] -7,8- difluoro-quinoline-3-carboxamide, (15.077) N-[(lS)-l-benzyl-l,3-dimethyl-butyl]-7,8-difluoro-quinoline- 3 -carboxamide, (15.078) N-[(2R)-2,4-dimethyl-l-phenylpentan-2-yl]-8-fluoroquinoline-3-carboxamide, ( 15.079) rac-2-benzyl -N-(8-fluoro-2 -methyl -3-quinolyl)-2,4-dimethyl-pentanamide, ( 15.080) (5RS)-3-[3- (3 -cyclopropyl-2-fluorophenoxy)-6-methylpyridazin-4-yl] -5 -(2,4-dimethylbenzyl)-5 ,6-dihydro-4H- 1 ,2,4- oxadiazine, (15.081) (5S)-3-[3-(3-cyclopropyl-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2,4- dimethylbenzyl)-5,6-dihydro-4H-l,2,4-oxadiazine, (15.082) (5RS)-5-(4-bromo-2-methylbenzyl)-3-[3-(3- chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl] -5 ,6-dihydro-4H- 1 ,2,4-oxadiazine, (15.083) (5RS)-3 -[3 - (3 -chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl] -5-(2-chloro-4-methylbenzyl)-5 ,6-dihydro-4H- 1 ,2,4-oxadiazine, (15.084) (5S)-5-(4-bromo-2-methylbenzyl)-3-[3-(3-chloro-2-fluorophenoxy)-6- methylpyridazin-4-yl]-5,6-dihydro-4H-l,2,4-oxadiazine, (15.085) (5R)-3-[3-(3-chloro-2-fluorophenoxy)-6- methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-l,2,4-oxadiazine, (15.086) (5S)-3-[3- (3 -chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl] -5-(2-chloro-4-methylbenzyl)-5 ,6-dihydro-4H- 1 ,2,4- oxadiazine, (15.087) 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(2,4-dimethylphenyl)-2,2- difluoroethyl]-5-methylpyridazine-4-carboxamide, (15.088) 3-(3-bromo-2-fluoro-phenoxy)-6-chloro-N-[2- (2-chloro-4-methylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carbox-amide, (15.089) 6-chloro-N- [2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-(3-cyclopropyl-2-fluoro-phenoxy)-5-methylpyridazine- 4-carboxamide, (15.090) 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(3,4-dimethylphenyl)-2,2- difluoroethyl]-5-methylpyridazine-4-carboxamide, (15.091) 6-chloro-3-(3-chloro-2-fluorophenoxy)-N-[2- (2,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carbox-amide, (15.092) N-[2-(2-bromo-4- methylphenyl)-2,2-difluoroethyl] -6-chloro-3 -(3 -cyclopropyl-2-fluoro-phenoxy)-5 -methylpyridazine-4- carboxamide, (15.093) l,l-diethyl-3-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.094) l,3-dimethoxy-l-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.095) 1- [[3-fluoro-4-(5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl)phenyl]methyl]azepan-2-one, (15.096) l-[[4-[5- (trifluoromethyl)- 1 ,2,4-oxadiazol-3 -yl]phenyl]methyl]piperidin-2-one, ( 15.097) 1 -methoxy- 1 -methyl-3- [[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.098) l-methoxy-3-methyl-l-[[4-[5- (trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.099) 2-(difluoromethyl)-5-[2-[l-(2,6- difluorophenyl)cyclopropoxy]pyrimidin-5-yl]-l,3,4-oxadiazole, (15.100) 2,2-difluoro-N-methyl-2-[4-[5- (trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]acetamide, (15.101) 3,3-dimethyl-l-[[4-[5-(trifluoromethyl)-1.2.4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-one, (15.102) 3-ethyl-l-methoxy-l-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.103) 4,4-dimethyl-l-[[4-[5-(trifluoromethyl)- l,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one, (15.104) 4,4-dimethyl-2-[[4-[5- (trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, (15.105) 4-[5-(trifluoromethyl)-1.2.4-oxadiazol-3-yl]phenyl dimethylcarbamate, (15.106) 5 ,5 -dimethyl -2-[[4-[5 -(trifluoromethyl)- 1 ,2,4- oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3 -one, (15.107) 5 -[5 -(difluoromethyl)- 1 ,3 ,4-oxadiazol-2-yl] -N- [(lR)-l-(2,6-difluorophenyl)ethyl]pyrimidin-2-amine, (15.108) 5-[5-(difluoromethyl)-l,3,4-oxadiazol-2- yl]-N-[(lR)-l-(2,6-difluorophenyl)propyl]pyrimidin-2-amine, (15.109) 5-[5-(difluoromethyl)-l,3,4- oxadiazol-2-yl]-N-[(lR)-l-(2-fluorophenyl)ethyl]pyrimidin-2 -amine, (15.110) 5-[5-(difluoromethyl)-l,3,4- oxadiazol-2-yl]-N-[(lR)-l-(2-fluorophenyl)ethyl]pyrimidin-2 -amine, (15.111) 5-[5-(difluoromethyl)-l,3,4- oxadiazol-2-yl] -N-[( 1 R)- 1 -(3 ,5-difluorophenyl)ethyl]pyrimidin-2-amine, (15.112) 5 - [5 -(difluoromethyl)-1.3.4-oxadiazol-2-yl]-N-[(lR)-l-phenylethyl]pyrimidin-2-amine, (15.113) 5 -[5 -(difluoromethyl)- 1,3,4- oxadiazol-2-yl]-N-[l-(2-fluorophenyl)cyclopropyl]pyrimidin-2 -amine, (15.114) 5-methyl-l-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one, (15.115) ethyl l-{4-[5- (trifluoromethyl)-l,2,4-oxadiazol-3-yl]benzyl}-lH-pyrazole-4-carboxylate, (15.116) methyl {4-[5- (trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl}carbamate, (15.117) N-(l-methylcyclopropyl)-4-[5- (trifluoromethyl)-l,2,4-oxadiazol-3-yl]benzamide, (15.118) N-(2,4-difluorophenyl)-4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]benzamide, (15.119) N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]propanamide, (15.120) N,N-dimethyl-l-{4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]benzyl} - 1H- 1 ,2,4-triazol-3 -amine, (15.121) N-[(E)-methoxyiminomethyl] -4-[5 -(trifluoromethyl)- 1 ,2,4- oxadiazol-3-yl]benzamide, (15.122) N-[(E)-N-methoxy-C-methyl-carbonimidoyl]-4-[5-(trifluoromethyl)- l,2,4-oxadiazol-3-yl]benzamide, (15.123) N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-l,2,4- oxadiazol-3-yl]benzamide, (15.124) N-[(Z)-N-methoxy-C-methyl-carbonimidoyl]-4-[5-(trifluoromethyl)- l,2,4-oxadiazol-3-yl]benzamide, (15.125) N-[[2,3-difhioro-4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]-3,3,3-trifluoro-propanamide, (15.126) N-[[4-[5-(trifhioromethyl)-l,2,4-oxadiazol-3- yl]phenyl]methyl]propanamide, (15.127) N-[4-[5-(trifhioromethyl)-l,2,4-oxadiazol-3- yl]phenyl]cyclopropanecarboxamide, (15.128) N-{2,3-difhroro-4-[5-(trifhioromethyl)-l,2,4-oxadiazol-3- yl]benzyl}butanamide, (15.129) N-{4-[5-(trifhioromethyl)-l,2,4-oxadiazol-3- yl]benzyl}cyclopropanecarboxamide, (15.130) N-{4-[5-(trifhioromethyl)-l,2,4-oxadiazol-3- yl]phenyl}propanamide, (15.131) N-allyl-N-[[4-[5-(trifhioromethyl)-l,2,4-oxadiazol-3-yl]phenyl]- methyl]acetamide, (15.132) N-allyl-N-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]- propanamide, (15.133) N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]- methyl]propanamide, (15.134) N-methoxy-N-[[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]- methyl]cyclopropanecarboxamide, (15.135) N-methyl-4-[5 -(trifluoromethyl)- 1 ,2,4-oxadiazol-3 -yl] - benzamide, (15.136) N-methyl-4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]benzenecarbothioamide, (15.137) N-methyl-N-phenyl-4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]benzamide and (15.138) 2,2- difluoro-2-[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]acetic acid.If present, the total amount of further fungicide(s) is preferably from 0.1 to 25 % by weight, more preferably from 0.5 to 20 % by weight, most preferably from 1 to 10 % by weight.Preferably, the compositions according to the invention furthermore comprise at least one emulsifier.The emulsifier(s) can be ionic (cationic or anionic), amphoteric or non-ionic, and any mixtures thereof, including standard surface-active substances typically present in formulations of active agrochemical ingredients. Emulsifier(s) are in the following also referred to by the more general term surfactant(s).Preferably, at least one emulsifier is a non-ionic emulsifier, most preferably all emulsifiers present in the composition according to the invention are non-ionic.Examples of suitable non-ionic surfactants include, but are not limited to: polycondensates of ethylene oxide and propylene oxideo compounds based on ethylene oxide and propylene oxide, having mean molar masses between 200 and 10 000 and preferably 1000 to 4000 g / mol, where the proportion by mass of the polyethoxylated block varies between 10% and 80%. polycondensates of ethylene oxide and / or propylene oxide with fatty alcohols o polyethylene glycol ethers of branched or linear alcohols, o polypropylene glycol ethers of branched or linear alcohols, o polycondensates of polyethylene and polypropylene glycol ethers of branched or linear alcohols, whereby the polyethylene and polypropylene sections of the surfactant can be grafted next to each other, or they can be randomly interspersed, o end group-capped and non-end group-capped alkoxylated linear and branched, saturated and unsaturated alcohols (e.g. butoxy polyethylene -polypropylene glycols). polycondensates of ethylene oxide and / or propylene oxide with fatty acids o reaction products of fatty acids or fatty acid alcohols with ethylene oxide and / or propylene oxide. polycondensates of ethylene oxide and / or propylene oxide with phenols, substituted phenols (preferably alkylphenols or arylphenols): such as tristyrylphenol ethoxylate or alkylaryl polyglycol ethers or nonylphenol ethoxylate. polycondensates of ethylene oxide and / or propylene oxide with fatty amines. polyoxyethylene fatty acid esters such as castor oil ethoxylate. polyoxyethylene fatty alcohol ethers. fatty esters of polyols (such as fatty acid esters of glycerol, sorbitol or sucrose), and ethoxylates thereof, such as esters of polyglycerin ethoxylates, or ester of ethoxylated sorbitol . fatty esters of alkanolamides. methylcellulose. polyvinyl alcohol. polyvinylpyrrolidone (PVP)o copolymer of PVP and dimethylaminoethyl methacrylate, o butylated PVP. copolymers of polyvinyl alcohol and polyvinylpyrrolidone . copolymers of (meth)acrylic acid and (meth)acrylic acid esters. polyoxyalkylenamines. polyoxyethylene alkanediol. polyoxy ethlyene and / or polyoxypropylene alkyne diols. copolymer of vinyl chloride and vinyl acetate and partially hydrolysed vinyl acetate. modified cellulose types. alkyl polyglucosides.Preferred non-ionic emulsifier(s) are selected from polycondensates of ethylene oxide and / or propylene oxide with fatty alcohols, selected from o polyethylene glycol ethers of branched or linear alcohols, o polypropylene glycol ethers of branched or linear alcohols, o polycondensates of polyethylene and polypropylene glycol ethers of branched or linear alcohols, whereby the polyethylene and polypropylene sections of the surfactant can be grafted next to each other, or they can be randomly interspersed, o end group-capped and non-end group-capped alkoxylated linear and branched, saturated and unsaturated alcohols (e.g. butoxy polyethylene -polypropylene glycols), polyoxyethylene fatty acid esters such as castor oil ethoxylate, and polycondensates of ethylene oxide and / or propylene oxide with phenols, substituted phenols (preferably alkylphenols or arylphenols): such as tristyrylphenol ethoxylate or alkylaryl polyglycol ethers or nonylphenol ethoxylate.More preferred non-ionic emulsifier(s) are selected frompolycondensates of polyethylene and polypropylene glycol ethers of branched or linear alcohols, preferably Lucramul® HOT, castor oil ethoxylates, preferably those listed in Table 1 below, more preferably Lucramul® CO30 and Emulsogen® EL 300, and - tristyrylphenol ethoxylates, preferably Soprophor® 796 / P and Soprophor® TS 54.Examples of suitable polyoxyethylene fatty acid esters are given in Table 1.Table 1:The total amount of non-ionic emulsifier(s) present in the compositions according to the invention is preferably from 1 to 30 % by weight, more preferably from 5 to 30 % by weight, more preferably from 10 to 30 % by weight, more preferably from 12 to 30 % by weight, more preferably from 14 to 30 % by weight, more preferably from 14 to 25 % by weight, more preferably from 14 to 23 % by weight, and most preferably from 14 to 21 % by weight.Examples of suitable anionic surfactants, if present, include, but are not limited to: salts of polyacrylic acid, salts of polymers of mixtures of acrylic acid / acrylate esters , salts of polymers of mixtures of acrylic acid / styrene, salts of lignosulfonic acid (such as sodium lignosulfonate), salts of phenolsulfonic acid, salts of condensation products of phenolsulphonic acid and formaldehyde, salts of naphthalenesulfonic acid, salts of naphthalenesulphonic acid and formaldehyde condensation products, salts of sulfonates of condensed naphtalenes or alkyl napthtalenes, salts of sulfonates of dodecyl- and tridecylbenzenes, salts of sulfosuccinic or sulfosuccinamate esters, salts of alkyl sulfates, salts of alkyl polyethoxylated and / or polypropoxylated sulfates, salts of paraffin sulfonates, salts of alkyl sulfonates, salts of alkyl polyethoxylated and / or polypropoxylated sulfonates, salts of aryl sulfates, salts of aryl polyethoxylated and / or polypropoxylated sulfates, salts of aryl sulfonates, salts of aryl polyethoxylated and / or polypropoxylated sulfonates, salts of alkylaryl sulfates, salts of alkylaryl polyethoxylated and / or polypropoxylated sulfates, salts of alkylaryl sulfonates, salts of alkylaryl polyethoxylated and / or polypropoxylated sulfonates, salts of diphenyl sulfonates, and of diphenyloxide sulfonates, salts of alpha-olefmsulfonates, salts of sulfonates of fatty acids and oils, salts of alpha-sulfonated methyl esters, salts of taurine derivatives, alkyl taurates, salts of isethionates, salts of alkyl phosphoric esters,salts of aryl phosphoric esters, salts of alkylaryl phosphoric esters, salts of phosphoric esters of polyethoxylated and / or polypropoxylated aliphatic linear or branched alcohols, salts of phosphoric esters of polyethoxylated and / or polypropoxylated aryl alcohols, protein hydrolysates, lignosulfite waste liquors, salts of polystyrenesulphonic acids, salts of polyvinylsulphonic acids, salts of carboxylates, salts of ether carboxylates.Any reference to salts in this paragraph refers preferably to the respective alkali, alkaline earth and ammonium salts.Examples of suitable cationic surfactants, if present, include, but are not limited to: those that contain units comprising primary, secondary, tertiary and / or quaternary amine groups that can either form part of the main polymer chain or can be borne by a side substituent directly connected thereto, cationic polymers based on acrylamide and / or methacrylamide,N-vinylpyrrolidone, quatemized N,N-dimethylamino methacrylate, diallyldimethylammonium chloride, quatemized vinylimidazole, e.g. 3-methyl-l-vinyl-lH-imidazol-3-ium chloride, acrylamidopropyltrimonium chloride, cassia hydroxypropyltrimonium chloride, guar hydroxypropyltrimonium chloride and polygalactomannan 2-hydroxypropyltrimethyl- ammonium chloride ether, starch hydroxypropyltrimonium chloride and cellulose hydroxypropyltrimonium chloride, polyquatemium-5, polyquatemium-6, polyquatemium-7, polyquatemium-10, polyquatemium-11, polyquatemium-16, polyquatemium-22, polyquatemium-28, polyquatemium-43, polyquatemium- 44, polyquatemium-46.Examples of suitable amphoteric surfactants, if present include, but are not restricted to: aminopropionates and iminodipropionates,imidazoline derivatives, such as amphodiacetates, amphodipropionates, amphohydroxypropylsulfonates, betaines, sultaines, phosphobetaines, amine oxides.If present, the total amount of anionic, cationic and / or amphoteric emulsifier(s) present in the compositions according to the invention is preferably from 0.01 to 10 % by weight, more preferably from 0.1 to 10 % by weight, more preferably from 0.1 to 5 % by weight, and most preferably from 0.1 to 1 % by weight.Preferably, the compositions according to the invention furthermore comprise at least one solvent different from N-(n-butyl)-2 -pyrrolidone.Examples of suitable further solvents include polar and nonpolar organic chemical liquids, for example from the classes of: aromatic and nonaromatic hydrocarbons, such as cyclohexane, paraffins, alkylbenzenes, xylene, toluene, tetrahydronaphthalene, alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, alcohols and polyols, which may optionally also be substituted, etherified and / or esterified, such as ethanol, propanol, butanol, benzylalcohol, cyclohexanol, glycol, 2-ethyl hexanol, ethers such as o dioctyl ether, tetrahydrofuran, dimethyl isosorbide, solketal, cyclopentyl methyl ether, dibenzyl ether, o the Dowanol glycol ether products of Dow, or different grades of polyethylene glycol ethers (e.g. ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monobutyl ether, ethylene glycol monophenyl ether, ethylene glycol monobenzyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monopropyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monobutyl ether, diethylene glycol monophenyl ether, diethylene glycol monobenzyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, triethylene glycol monopropyl ether, triethylene glycol monoisopropyl ether, triethylene glycol monobutyl ether, triethylene glycol monophenyl ether, triethylene glycol monobenzyl ether),o different grades of polypropylene glycol ethers (e.g. propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monoisopropyl ether, propylene glycol monobutyl ether, propylene glycol monophenyl ether, propylene glycol monobenzyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monopropyl ether, dipropylene glycol monoisopropyl ether, dipropylene glycol monobutyl ether, dipropylene glycol monophenyl ether, dipropylene glycol monobenzyl ether, tripropylene glycol monomethyl ether, tripropylene glycol monoethyl ether, tripropylene glycol monopropyl ether, tripropylene glycol monoisopropyl ether, tripropylene glycol monobutyl ether, tripropylene glycol monophenyl ether, tripropylene glycol monobenzyl ether), o anisole, phenetole, o different molecular weight grades of dimethyl polyethylene glycol, different molecular weight grades of dimethyl polypropylene glycol, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, cyclohexanone, cycloheptanone, acetophenone, propiophenone, esters (also including methylated fats and oils such as rapeseed oil methyl ester, soybean oil methyl ester, coconut oil methyl ester, 2-ethyl hexyl palmitate, 2-ethyl hexyl stearate), such as butyl propionate, pentyl propionate, methyl hexanoate, methyl octanoate, methyl decanoate, 2-ethyl-hexyl acetate, benzyl acetate, cyclohexyl acetate, isobomyl acetate, benzyl benzoate, butyl benzoate, isopropyl benzoate, di / triesters such as dimethyl succinate, dimethyl glutarate, dimethyl adipate, diisopropyl adipate, dibutyl adipate, benzyl-2 -ethylhexyl adipate, dimethyl 2-methyl glutarate, monoacetin, diacetin, triacetin, trimethyl citrate, triethyl citrate, triethyl acetyl citrate, tributyl citrate, tributyl acetyl citrate, as well as mixtures and blends thereof, lactate esters, such as methyl lactate, ethyl lactate, propyl lactate, butyl lactate, 2-ethyl hexyl lactate, (poly)ethers such as different molecular weight grades of polyethylene glycol, different molecular weight grades of polypropylene glycol, unsubstituted and substituted amines, amides (such as dimethylformamide, or N,N-dimethyl lactamide, or N-formyl morpholine, or fatty acid amides such N,N-dimethyl decanamide or N,N-dimethyl dec-9-en-amide) and esters thereof such as methyl 6-(dimethylamino)-2-methyl-6-oxo-hexanoate,lactams (such as 2-pyrrolidone, N-alkylpyrrolidones different from N-butylpyrrolidone, such as N- methylpyrrolidone, N-octylpyrrolidone, N-dodecylpyrrolidone, N-methyl caprolactam, N-alkyl caprolactam), lactones (such as gamma-butyrolactone, gamma-valerolactone, delta-valerolactone, alpha-methyl gamma-butyrolactone), sulfones and sulfoxides (such as dimethyl sulfoxide), oils of vegetable or animal origin such as sunflower oil, rapeseed oil, com oil, nitriles, such as linear or cyclic alkyl nitriles, in particular acetonitrile, cyclohexane carbonitrile, octanonitrile, dodecanonitrile, linear and cyclic carbonates, such as dimethyl carbonate, diethyl carbonate, dipropyl carbonate, diisopropyl carbonate, dibutyl carbonate and isomers thereof, diphenyl carbonate, ethylene carbonate, trimethylene carbonate, propylene carbonate, glycerol carbonate, butylene carbonate, pentylene carbonate, hexylene carbonate and octylene carbonate, phosphates, such as triethyl phosphate, tributyl phosphate, triisobutyl phosphate, trioctyl phosphate, tris(2-ethyl hexyl) phosphate, white mineral oils, mixtures of the any of the above such as, o ester mixtures such as Rhodiasolv RPDE, o mixtures of morpholine derivatives and cyclic carbonates such as Armid FMPC, o mixtures of dimethyl sulfoxide with esters and / or with glycerine derivatives.Preferably, the solvent different from N-(n-butyl)-2-pyrrolidone is selected from the group consisting of amides, substituted amines, aromatic hydrocarbons, methylated fats and oils, and mixtures thereof.More preferably, the solvent different from N-(n-butyl)-2 -pyrrolidone is selected from the group consisting of N,N-dimethyloctanamide, N,N-dimethyldecanamide, 5-(dimethylamino)-2-methyl-5-oxopentanoate methyl ester, aromatic hydrocarbons, soybean fatty acid methyl ester and mixtures thereof.More preferably, the solvent different from N-(n-butyl)-2 -pyrrolidone is selected from the group consisting of N,N-dimethyloctanamide, N,N-dimethyldecanamide, 5-(dimethylamino)-2-methyl-5-oxopentanoate methyl ester, aromatic hydrocarbons and mixtures thereof.Most preferably, the solvent different from N-(n-butyl)-2-pyrrolidone is selected from the group consisting ofN,N-dimethyloctanamide, N,N-dimethyldecanamide, preferably Genagen® 4166, Genagen® 4296, 5-(dimethylamino)-2-methyl-5-oxopentanoate methyl ester, preferably Rhodiasolv Polarclean®, aromatic hydrocarbons, preferably solvent naphtha, particularly preferred Solvesso® 200 ND, and mixtures thereof.Preferably, the total amount of solvent(s) different from N-(n-butyl)-2 -pyrrolidone is from 20 to 80 % by weight, preferably from 25 to 80 % by weight, more preferred from 30 to 80 % by weight, more preferred from 30 to 75 % by weight, and most preferably from 30 to 70 % by weight.Preferably, the compositions according to the invention furthermore comprise at least one additive. Additives suitable for emulsifiable concentrates are known to those skilled in the art and include, but are not limited to antifoams, penetration enhancers, wetting agents, spreading agents, retention agents, preservatives, antioxidants, light stabilizers, antifreezes, dyes and pigments.Suitable preservatives by way of example are dichlorophene and benzyl alcohol hemiformal, 5-chloro-2- methyl-4-isothiazolin-3-one [CAS-No. 26172-55-4], 2-methyl-4-isothiazolin-3-one [CAS-No. 2682-20-4] and 1.2-benzisothiazol-3(2H)-one [CAS-No. 2634-33-5], Commercial products which may be mentioned are Preventol® D7 (Lanxess), Kathon® CG / ICP (Dow), Acticide® SPX (Thor GmbH) and Proxel® GXL (Arch Chemicals).Suitable antifreezes by way of example are propylene glycol, ethylene glycol, urea, glycerine, inorganic salts, e.g. sodium chloride, potassium chloride, sodium sulfate and potassium sulfate.Suitable dyes and pigments by way of example are inorganic pigments, e.g. iron oxide, titanium oxide and Prussian Blue, carbon black, zinc oxide, and organic dyes, e.g. alizarin, azo and metal phthalocyanine dyes.Preferably, the additive(s) are selected from antifoams, preservatives, antioxidants, light stabilizers, antifreezes, dyes and pigments, more preferably from antifoams, preservatives, antioxidants and light stabilizers.Preferably, the total amount of additive(s) is from 0.01 to 2 % by weight, preferably from 0.01 to 1.5 % by weight, more preferred from 0.01 to 1 % by weight, and most preferably from 0.05 to 0.5 % by weight.Most preferably, the compositions according to the invention comprise at least one antifoam.Suitable antifoams by way of example aresilicone antifoams and magnesium stearate, silicone oils, silicone oil preparations, particularly nonionic aqueous polydimethylsiloxane -based emulsions (dimethyl siloxanes and silicones, CAS No. 63148-62-9). Examples are Silcolapse® 426 and 432 from Bluestar Silicones, Silfoam® SRE and SC132 from Wacker, SAG 1572 and SAG 30 from Momentive.Preferably, the antifoam(s) are selected from Silcolapse® 426 and 432 from Bluestar Silicones, Silfoam® SRE and SC132 from Wacker, SAG 1572 and SAG 30 from Momentive.Preferably, the total amount of antifoam(s) is from 0.01 to 1 % by weight, preferably from 0.01 to 0.5 % by weight, more preferred from 0.05 to 0.3 % by weight, and most preferably from 0.05 to 0.2 % by weight.Preferred compositions according to the invention comprise(A) methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl] -2 -hydroxy-3 -( 1 ,2,4-triazol- 1 -yl)propanoate,(B) N-(n-butyl)-2-pyrrolidone,(C) at least one emulsifier, preferably non-ionic emulsifier, more preferably non-ionic emulsifier selected from poly condensates of polyethylene and polypropylene glycol ethers of branched or linear alcohols, preferably Lucramul® HOT, castor oil ethoxylates, preferably Lucramul® CO30 and Emulsogen® EL 300, and tristyrylphenol ethoxylates, preferably Soprophor® 796 / P and Soprophor® TS 54, and mixtures thereof,(D) at least one solvent different from N-(n-butyl)-2 -pyrrolidone, preferably selected fromN,N-dimethyloctanamide, N,N-dimethyldecanamide, preferably Genagen® 4166, Genagen® 4296,5-(dimethylamino)-2-methyl-5-oxopentanoate methyl ester, preferably Rhodiasolv Polarclean®, aromatic hydrocarbons, preferably solvent naphtha, particularly preferred Solvesso®200 ND, and mixtures thereof, and(E) optionally, at least one additive, preferably antifoam, more preferably antifoam selected from silicone oils and silicone oil preparations, most preferably selected from Silcolapse® 426 and 432 from Bluestar Silicones, Silfoam® SRE and SC132 from Wacker, SAG 1572 and SAG 30 from Momentive, and mixtures thereof.More preferred compositions according to the invention comprise(A) 1 to 50 % by weight methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(l,2,4- triazol- 1 -yl)propanoate,(B) 9 to 70 % by weight N-(n-butyl)-2 -pyrrolidone,(C) at least one emulsifier, preferably non-ionic emulsifier, more preferably non-ionic emulsifier selected from poly condensates of polyethylene and polypropylene glycol ethers of branched or linear alcohols, preferably Lucramul® HOT, castor oil ethoxylates, preferably Lucramul® CO30 and Emulsogen® EL 300, and tristyrylphenol ethoxylates, preferably Soprophor® 796 / P and Soprophor® TS 54, and mixtures thereof, wherein the total amount of non-ionic emulsifier(s) present in the compositions according to the invention is from 1 to 30 % by weight,(D) at least one solvent different from N-(n-butyl)-2 -pyrrolidone, preferably selected fromN,N-dimethyloctanamide, N,N-dimethyldecanamide, preferably Genagen® 4166, Genagen® 4296,5-(dimethylamino)-2-methyl-5-oxopentanoate methyl ester, preferably Rhodiasolv Polarclean®, aromatic hydrocarbons, preferably solvent naphtha, particularly preferred Solvesso® 200 ND, and mixtures thereof, wherein the total amount of solvent(s) different from N-(n-butyl)-2-pyrrolidone is from 20 to 80 % by weight, and(E) optionally, at least one additive, preferably antifoam, more preferably antifoam selected from silicone oils and silicone oil preparations, most preferably selected from Silcolapse® 426 and 432 from Bluestar Silicones, Silfoam® SRE and SC132 from Wacker, SAG 1572 and SAG 30 from Momentive, and mixtures thereof, wherein the total amount of antifoam(s) is from 0.01 to 1 % by weight.Even more preferred compositions according to the invention comprise(A) 7 to 11 % by weight methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(l,2,4- triazol- 1 -yl)propanoate,(B) 9 to 40 % by weight N-(n-butyl)-2-pyrrolidone,(C) at least one emulsifier, preferably non-ionic emulsifier, more preferably non-ionic emulsifier selected from poly condensates of polyethylene and polypropylene glycol ethers of branched or linear alcohols, preferably Lucramul® HOT, castor oil ethoxylates, preferably Lucramul® CO30 and Emulsogen® EL 300, and tristyrylphenol ethoxylates, preferably Soprophor® 796 / P and Soprophor® TS 54, wherein the total amount of non-ionic emulsifier(s) present in the compositions according to the invention is from 14 to 21 % by weight,(D) at least one solvent different from N-(n-butyl)-2-pyrrolidone, preferably selected fromN,N-dimethyloctanamide, N,N-dimethyldecanamide, preferably Genagen® 4166, Genagen® 4296,5-(dimethylamino)-2-methyl-5-oxopentanoate methyl ester, preferably Rhodiasolv Polarclean®, aromatic hydrocarbons, preferably solvent naphtha, particularly preferred Solvesso® 200 ND, and mixtures thereof, wherein the total amount of solvent(s) different from N-(n-butyl)-2-pyrrolidone is from 30 to 70 % by weight, and(E) optionally, at least one additive, preferably antifoam, more preferably antifoam selected from silicone oils and silicone oil preparations, most preferably selected from Silcolapse® 426 and 432 from Bluestar Silicones, Silfoam® SRE and SC132 from Wacker, SAG 1572 and SAG 30 from Momentive, and mixtures thereof, wherein the total amount of antifoam(s) is from 0.05 to 0.2 % by weight.The emulsifiable concentrates according to the invention may be prepared by sequential mixing of all components until a homogeneous liquid is obtained. The order of addition is inconsequential, and the mixing may be performed at any temperature, as long as the components are fluid. An example of a process is as follows: Compound (I) and further active ingredient(s), if any, are charged into a suitable reaction vessel (e.g. glass flask, or stainless steel reactor equiped with stirring equipment). The remaining components (B), and optionally (C), (D) and (E) are added to the reaction vessel, and the mixture is agitated at room temperature, or above room temperature, until a homogeneous mixture has been obtained.The invention further relates to a method for controlling harmful microorganisms, in particular phytopathogenic fungi, in crop protection and in the protection of materials, wherein a composition according to the invention is applied to the harmful microorganisms and / or their habitat.Preferably, before applying said compositions to the harmful microorganisms and / or their habitat, e.g. the plant in need of treatment or a part thereof, the composition is diluted with water. More preferably, the emulsifiable concentrate is mixed with water in such amount to arrive at a total concentration of active ingredients in the resulting mixture of 0.1 to 5, preferably 0.2 to 2, more preferred 0.25 to 1.5 g / 1.The compositions according to the invention and spray solutions derived therefrom by dilution with water, have very good fungicidal properties and can be used in crop protection, for example for control of Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.The compositions according to the invention can be used for curative or protective control of phytopathogenic fungi. The invention therefore also relates to curative and protective methods for controlling phytopathogenic fungi by the use of the inventive compositions, which are applied to the seed, the plant or plant parts, the fruit or the soil in which the plants grow.PlantsAll plants and plant parts can be treated in accordance with the invention. Plants are understood here to mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants may be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of thesemethods, including the transgenic plants and including the plant cultivars which are protectable and non- protectable by plant breeders’ rights. Plant parts are understood to mean all parts and organs of plants above and below the ground, such as shoot, leaf, flower and root, examples of which include leaves, needles, stalks, stems, flowers, fruit bodies, fruits and seeds, and also roots, tubers and rhizomes. The plant parts also include harvested material and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, slips and seeds.Plants which can be treated in accordance with the invention include the following: cotton, flax, grapevine, fruit, vegetables, such as Rosaceae sp. (for example pome fruits such as apples and pears, but also stone fruits such as apricots, cherries, almonds and peaches, and soft fruits such as strawberries), Ribesioidae sp. , Juglandaceae sp., Betulaceae sp., Anaccirdicicecie sp., Fagcicecie sp., Moraceae sp., Oleacecie sp., Actinidacecie sp. , Lauracecie sp. , Musaceae sp. (for example banana trees and plantations), Rubiacecie sp. (for example coffee), Theacecie sp., Sterculiceae sp., Rutaceae sp. (for example lemons, oranges and grapefruit); Solanaceae sp. (for example tomatoes), Liliacecie sp., Asteraceae sp. (for example lettuce), Umbelliferae sp. , Cruciferae sp. , Chenopodiacecie sp. , Cucurbitaceae sp. (for example cucumber), Alliacecie sp. (for example leek, onion), Papilioncicecie sp. (for example peas); major crop plants, such as Graminecie sp. (for example maize, turf, cereals such as wheat, rye, rice, barley, oats, millet and triticale), Asteraceae sp. (for example sunflower), Brassicaceae sp. (for example white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, pak choi, kohlrabi, radishes, and oilseed rape, mustard, horseradish and cress), Fabacae sp. (for example bean, peanuts), Papilionaceae sp. (for example soya bean), Solanaceae sp. (for example potatoes), Chenopodiaceae sp. (for example sugar beet, fodder beet, swiss chard, beetroot); useful plants and ornamental plants for gardens and wooded areas; and genetically modified varieties of each of these plants.PathogensNon-limiting examples of pathogens of fungal diseases which may be treated in accordance with the invention include: diseases caused by powdery mildew pathogens, for example Blumeria species, for example Blumeria graminis,' Podosphaera species, for example Podosphaera leucotricha,' Sphaerotheca species, for example Sphaerotheca fuliginea,' Uncinula species, for example Uncinula necator, diseases caused by rust disease pathogens, for example Gymnosporangium species, for example Gymnosporangium sabinae,' Hemileia species, for example Hemileia vastatrix,' Phakopsora species, for example Phakopsora pachyrhizi or Phakopsora meibomiae'. Puccinia species, for example Puccinia recondita, Puccinia graminis oder Puccinia striiformis,' Uromyces species, for example Uromyces appendiculatus, 'diseases caused by pathogens from the group of the Oomycetes, for example Albugo species, for example Albugo Candida, Bremia species, for example Bremia lactucac, Peronospora species, for example Peronospora pisi or P. brassicac, Phytophthora species, for example Phytophthora infestans,' Plasmopara species, for example Plasmopara viiicolcr. Pseudoperonospora species, for example Pseudoperonospora humuli or Pseudoperonospora cubensis,' Pythium species, for example Pythium uliimunr. leaf blotch diseases and leaf wilt diseases caused, for example, by Alternaria species, for example Alternaria solani,' Cercospora species, for example Cercospora beiicolcr. Cladiosporium species, for example Cladiosporium cucumerinunr. Cochliobolus species, for example Cochliobolus sativus (conidial form: Drechslera, syn: Helminthosporium) or Cochliobolus miyabeanus,' Colletotrichum species, for example Colletotrichum Undemuihaniunr. Corynespora species, for example Corynespora cassiicolcr. Cycloconium species, for example Cycloconium oleaginunr, Diaporthe species, for example Diaporthe citri,' Elsinoe species, for example Elsinoe fawcettii,' Gloeosporium species, for example Gloeosporium laeticolor, Glomerella species, for example Glomerella cingulaicr. Guignardia species, for example Guignardia bidwelli,' Leptosphaeria species, for example Leptosphaeria maculans,' Magnaporthe species, for example Magnaporthe grisea,' Microdochium species, for example Microdochium nivale,' Mycosphaerella species, for example Mycosphaerella graminicola, Mycosphaerella arachidicola or Mycosphaerella fijiensis’. Phaeosphaeria species, for example Phaeosphaeria nodorunr. Pyrenophora species, for example Pyrenophora teres or Pyrenophora tritici repentis,' Ramularia species, for example Ramularia collo-cygni or Ramularia areola,' Rhynchosporium species, for example Rhynchosporium secalis,' Septoria species, for example Septoria apii or Septoria lycopersici,' Stagonospora species, for example Stagonospora nodorunr, Typhula species, for example Typhula incarnata,' Venturia species, for example Venturia inaequalis,' root and stem diseases caused, for example, by Corticium species, for example Corticium graminearunr, Fusarium species, for example Fusarium oxysporunr, Gaeumannomyces species, for example Gaeumannomyces graminis,' Plasmodiophora species, for example Plasmodiophora brassicae,' Rhizoctonia species, for example Rhizoctonia solani,' Sarocladium species, for example Sarocladium oryzae,' Sclerotium species, for example Sclerotium oryzae,' Tapesia species, for example Tapesia acuformis,' Thielaviopsis species, for example Thielaviopsis basicola,' ear and panicle diseases (including com cobs) caused, for example, by Alternaria species, for example Alternaria spp:, Aspergillus species, for example Aspergillus flavus,' Cladosporium species, for example Cladosporium cladosporioides,' Claviceps species, for example Claviceps purpurea,' Fusarium species, for example Fusarium culmorunr, Gibberella species, for example Gibberella zeae Monographella species, for example Monographella nivalis,' Stagnospora species, for example Stagnospora nodorunr,diseases caused by smut fungi, for example Sphacelotheca species, for example Sphacelotheca reiliana, Tilletia species, for example Tilletia caries or Tilletia coniroverscr. Urocystis species, for example Urocystis occulta^ Ustilago species, for example Ustilago nuda,' fruit rot caused, for example, by Aspergillus species, for example Aspergillus flavus'. Botrytis species, for example Botrytis cinerecr. Monilinia species, for example Monilinia laxa, Penicillium species, for example Penicillium expansum or Penicillium purpurogenunr. Rhizopus species, for example Rhizopus stolon if er'. Sclerotinia species, for example Sclerotinia scleroliorunr. Verticilium species, for example Verticilium alboairunr. seed- and soil -borne rot and wilt diseases, and also diseases of seedlings, caused, for example, by Alternaria species, for example Alternaria brassicicolcr. Aphanomyces species, for example Aphanomyces euieiches'. Ascochyta species, for example Ascochyta lends,' Aspergillus species, for example Aspergillus flavus'. Cladosporium species, for example Cladosporium herbarum,' Cochliobolus species, for example Cochliobolus sativus (conidial form: Drechslera, Bipolaris Syn: Hehninthosporiumf, Colletotrichum species, for example Colletotrichum coccodes,' Fusarium species, for example Fusarium culmorunr, Gibberella species, for example Gibberella zeae Macrophomina species, for example Macrophomina phaseolina,' Microdochium species, for example Microdochium nivale,' Monographella species, for example Monographella nivalis,' Penicillium species, for example Penicillium expansum,' Phoma species, for example Phoma lingam,' Phomopsis species, for example Phomopsis sojae'. Phytophthora species, for example Phytophthora cactorunr, Pyrenophora species, for example Pyrenophora graminea,' Pyricularia species, for example Pyricularia oryzae,' Pythium species, for example Pythium ultimum, Rhizoctonia species, for example Rhizoctonia solani,' Rhizopus species, for example Rhizopus oryzae,' Sclerotium species, for example Sclerotium rolfsii,' Septoria species, for example Septoria nodorunr, Typhula species, for example Typhula incarnata,' Verticillium species, for example Verticillium dahliae,' cancers, galls and witches’ broom caused, for example, by Nectria species, for example Nectria galligena,' wilt diseases caused, for example, by Verticillium species, for example Verticillium longisporunr, Fusarium species, for example Fusarium oxysporunr, deformations of leaves, flowers and fruits caused, for example, by Exobasidium species, for example Exobasidium vexans,' Taphrina species, for example Taphrina deformans,' degenerative diseases in woody plants, caused, for example, by Esca species, for example Phaeomoniella chlamydospora, Phaeoacremonium aleophilum or Fomitiporia mediterranea,' Ganoderma species, for example Ganoderma boninensc.diseases of plant tubers caused, for example, by Rhizoctonia species, for example Rhizoctonia solani.' Helminthosporium species, for example Helminthosporium solani'. diseases caused by bacterial pathogens, for example Xanthomonas species, for example Xanthomonas campestris pv. oryzac, Pseudomonas species, for example Pseudomonas syringae pv. lachrymans,' Erwinia species, for example Erwinia amylovorcr. Liberibacter species, for example Liberibacter asiaticus,' Xyella species, for example Xylella fastidiosa, Ralstonia species, for example Ralstonia solanacearum,' Dickeya species, for example Dickeya solani,' Clavibacter species, for example Clavibacter michiganensis,' Streptomyces species, for example Streptomyces scabies.Diseases of soya beans:Fungal diseases on leaves, stems, pods and seeds caused, for example, by Alternaria leaf spot (Alternaria spec, atrans tenuissima), Anthracnose (CoUeioi ichum gloeosporoides dematium var. truncatum), brown spot (Septoria glycines), cercospora leaf spot and blight (Cercospora kikuchii), choanephora leaf blight (Choanephora infundibulifera trispora (Syn.f), dactuliophora leaf spot (Dactuliophora glycines), downy mildew (Peronospora manshurica), drechslera blight (Drechslera glycini), frogeye leaf spot (Cercospora sojina), leptosphaerulina leaf spot (Leptosphaerulina trifolii), phyllostica leaf spot (Phyllosticta sojaecola), pod and stem blight (Phomopsis sojae), powdery mildew (Microsphaera diffusa), pyrenochaeta leaf spot (Pyrenochaeta glycines), rhizoctonia aerial, foliage, and web blight (Rhizoctonia solani), rust (Phakopsora pachyrhizi, Phakopsora meibomiae), scab (Sphaceloma glycines), stemphylium leaf blight (Stemphylium botryosum), sudden death syndrome (Fusarium virguliforme), target spot (Corynespora cassiicola).Fungal diseases on roots and the stem base caused, for example, by black root rot (Calonectria crotalariae), charcoal rot (Macrophomina phaseolina), fusarium blight or wilt, root rot, and pod and collar rot (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti), mycoleptodiscus root rot (Mycoleptodiscus terrestris), neocosmospora (Neocosmospora vasinfecta), pod and stem blight (Diaporthe phaseolorum), stem canker (Diaporthe phaseolorum var. caulivora), phytophthora rot (Phytophthora megasperma), brown stem rot (Phialophora gregata), pythium rot (Pythium aphanidermatum, Pythium irregulare, Pythium debaryanum, Pythium myriotylum, Pythium ultimum), rhizoctonia root rot, stem decay, and damping-off (Rhizoctonia solani), sclerotinia stem decay (Sclerotinia sclerotiorum), sclerotinia southern blight (Sclerotinia rolfsii), thielaviopsis root rot (Thielaviopsis basicola).Material ProtectionThe compositions according to the invention and spray solutions derived therefrom can also be used in the protection of industrial materials, for protection of industrial materials against attack and destruction by phytopathogenic fungi, and as antifouling agents.Industrial materials in the present context are understood to mean inanimate materials which have been prepared for use in industry. For example, industrial materials which are to be protected by inventive compositions from microbial alteration or destruction may be adhesives, glues, paper, wallpaper and board / cardboard, textiles, carpets, leather, wood, fibers and tissues, paints and plastic articles, cooling lubricants and other materials which can be infected with or destroyed by microorganisms. Parts of production plants and buildings, for example cooling-water circuits, cooling and heating systems and ventilation and air-conditioning units, which may be impaired by the proliferation of microorganisms may also be mentioned within the scope of the materials to be protected. Industrial materials within the scope of the present invention preferably include adhesives, sizes, paper and card, leather, wood, paints, cooling lubricants and heat transfer fluids, more preferably wood.The invention is illustrated by the examples below.ExamplesComparative composition (A) (EC50) and compositions according to the invention (B) (EC50), (C) (EC75) and (D) (EC 100) have been prepared by mixing the components listed in Table 2.Table 2:Each composition has been mixed with water to arrive at ready-to-use spray emulsions and applied with a conventional spraying device.The respective amount of water was adjusted to arrive at the same concentration of methyl 2-[2-chloro-4-(4- chlorophenoxy)phenyl]-2-hydroxy-3-(l,2,4-triazol-l-yl)propanoate in each spray emulsion, namely 1.5 g / 1. Each spray emulsion was applied at an application rate of 100 1 / ha.Due to necessary fdter inspection after each 4thloading of the spraying device tank, the sealing ring of the suction filter housing was contaminated with the respective spray emulsion.After exposure overnight the sealing rings have been inspected visually. Figure 1 shows (I) a sealing ring before contact with any spray emulsion and sealing rings after contact with spray emulsions resulting from comparative composition (A) and compositions according to the invention (C) and (D), respectively.The sealing ring in contact with the spray solution resulting from comparative composition (A) (marked in Figure 1 with (IV)) is considerably swollen and does not fit back in its housing as shown in Figure 2. In contrast, only very slight swelling is observed after contact with spray solutions resulting from compositions according to the invention (C) (marked in Figure 1 with (III)) and (D) (marked in Figure 1 with (II)), respectively.Key to Figures:(I) Sealing ring before contact with any spray emulsion.(II) Sealing ring after overnight exposure with spray solution (D).(III) Sealing ring after overnight exposure with spray solution (C).(IV) Sealing ring after overnight exposure with spray solution (A) (comparison).

Claims

Claims1. Composition comprising(A) methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(l,2,4-triazol-l-yl)propanoate, and(B) N-(n-butyl)-2-pyrrolidone.

2. Composition according to claim 1, wherein the composition comprises at least one emulsifier.

3. Composition according to at least one of claims 1 to 2, wherein the composition comprises at least one solvent different from N-(n-butyl)-2 -pyrrolidone.

4. Composition according to at least one of claims 1 to 3, wherein the composition comprises at least one additive.

5. Composition according to claim 1, wherein the composition comprises(A) methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl] -2 -hydroxy-3 -( 1 ,2,4-triazol- 1 -yl)propanoate,(B) N-(n-butyl)-2-pyrrolidone,(C) at least one emulsifier, and(D) at least one solvent different from N-(n-butyl)-2-pyrrolidone.

6. Composition according to claim 5, wherein the composition comprises(E) at least one additive.

7. Composition according to at least one of claims 1 to 6, wherein the composition comprises methyl 2- [2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(l,2,4-triazol-l-yl)propanoate in an amount of 1 to 50 % by weight.

8. Composition according to at least one of claims 1 to 7, wherein the composition comprises N-(n- butyl)-2 -pyrrolidone in an amount of 5 to 99 % by weight.

9. Composition according to claim 2 or 5, wherein the emulsifier is a non-ionic emulsifier.

10. Composition according to claim 9, wherein the total amount of non-ionic emulsifier(s) present in the composition is from 1 to 30 % by weight.

11. Composition according to claim 3 or 5, wherein the solvent is selected from the group consisting of N,N-dimethyloctanamide, N,N-dimethyldecanamide, 5-(dimethylamino)-2-methyl-5-oxopentanoate methyl ester, aromatic hydrocarbons, soybean fatty acid methyl ester and mixtures thereof.

12. Composition according to claim 3, 5 or 11, wherein the total amount of solvent(s) different from N- (n-butyl)-2 -pyrrolidone is from 20 to 80 % by weight.

13. Composition according to claim 4 or 6, wherein the additive is an antifoam.

14. Composition according to at least one of claims 1 to 13, wherein the composition comprises at least one fungicide different from methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(l,2,4- triazol- 1 -yl)propanoate .

15. Method for controlling harmful microorganisms in crop protection and in the protection of materials, characterized in that a composition according to at least one of claims 1 to 14 is applied to the harmful microorganisms and / or their habitat.