ACTIVE COMPOUND COMBINATIONS

Abstract

The present invention relates to active compound combinations, in particular within a fungicide composition, which comprises (A) a difluoromethyl-nicotinic indanyl carboxamide of formula (I) and a further fungicidally active compound (B). Moreover, the invention relates to a method for curatively or preventively controlling the phytopathogenic fungi of plants or crops, to the use of a combination according to the invention for the treatment of seed, to a method for protecting a seed and not at least to the treated seed.

Claims

1. Combination comprising: (A) at least one of formula (I) ##STR00004## in which X.sub.1, X.sub.2 independently represent H, halogen, C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.8-haloalkyl, C.sub.1-C.sub.8-alkyloxy, C.sub.1-C.sub.8-alkylsulfanyl, cyano; R.sup.1 represents H, C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.8-haloalkyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl, C.sub.1-C.sub.4-alkyl-C.sub.3-C.sub.8-cycloalkyl; C.sub.1-C.sub.4-alkyl-C.sub.3-C.sub.8-halocycloalkyl; R.sup.2, R.sup.3 independently represent H, C.sub.1-C.sub.8-alkyl, C.sub.1-C.sub.8-haloalkyl, C.sub.3-C.sub.8-cycloalkyl, C.sub.3-C.sub.8-halocycloalkyl, C.sub.1-C.sub.4-alkyl-C.sub.3-C.sub.8-cycloalkyl, C.sub.1-C.sub.4-alkyl-C.sub.3-C.sub.8-halocycloalkyl or an agrochemically acceptable salt thereof, and (B) at least one further active compound selected from the group of inhibitors of the ergosterol synthesis.

2. Combination according to claim 1 comprising at least one compound of the formula (I) in which X.sub.1 represents H; fluorine in 4-position of the pyridine ring; chlorine in 4-position of the pyridine ring; X.sub.2 represents H, fluorine in 4-position of the phenyl ring; chlorine in 4-position of the phenyl ring; ‘R.sup.1 represents methyl, ethyl, n-propyl, iso-propyl, butyl, iso-butyl, sec-butyl, —CH.sub.2-tbutyl; R.sup.2, R.sup.3 independently represent methyl, ethyl or isopropyl; or an agrochemically acceptable salt thereof.

3. Combination according to claim 1 comprising at least one compound of the formula (I) selected from the group consisting of: ##STR00005## ##STR00006##

4. Combination according to claim 1 comprising at least one further active compound (B) selected from the following group: (1) Inhibitors of the ergosterol biosynthesis, optionally (1.5) cyproconazole (113096-99-4), (1.7) difenoconazole (119446-68-3), (1.12) epoxiconazole (106325-08-0), (1.22) flutriafol (76674-21-0), (1.25) hexaconazole (79983-71-4), (1.30) metconazole (125116-23-6), (1.31) myclobutanil (88671-89-0), (1.39) prochloraz (67747-09-5), (1.40) propiconazole (60207-90-1), (1.41) prothioconazole (178928-70-6), (1.46) spiroxamine (118134-30-8), (1.47) tebuconazole (107534-96-3), (1.49) tetraconazole (112281-77-3), (1.51) triadimenol (89482-17-7).

5. Method for controlling phytopathogenic harmful fungi, comprising applying a combination according to claim 1 to the phytopathogenic harmful fungi and/or a habitat thereof.

6. Composition for controlling phytopathogenic harmful fungi, comprising at least one combination according to claim 1, in addition to one or more extenders and/or surfactants.

7. Composition according to claim 6 comprising at least one further active ingredient selected from the group of the insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, fertilizers, safeners and semiochemicals.

8. A product comprising a combination-according to claim 1 for control of phytopathogenic harmful fungi.

9. A product comprising a combination according to claim 1 as a plant growth regulator.

10. Process for producing a composition for controlling phytopathogenic harmful fungi, comprising mixing a combination according to claim 1 with one or more extenders and/or surfactants.

11. A product comprising a combination according to claim 1 for treatment of one or more transgenic plants.

12. A product comprising a combination according to claim 1 for treatment of seed and of seed of one or more transgenic plants.

Description

EXAMPLES

[0166] The advanced fungicidal activity of the active compound combinations according to the invention is evident from the example below. While the individual active compounds exhibit weaknesses with regard to the fungicidal activity, the combinations have an activity which exceeds a simple addition of activities.

[0167] A synergistic effect of fungicides is always present when the fungicidal activity of the active compound combinations exceeds the total of the activities of the active compounds when applied individually. The expected activity for 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

[0168] X is the efficacy when active compound A is applied at an application rate of m ppm (or g/ha),
Y is the efficacy when active compound B is applied at an application rate of n ppm (or g/ha),
E is the efficacy when the active compounds A and B are applied at application rates of m and n ppm (or g/ha), respectively, and
then

[00001]$E=X+Y-\frac{X.Math.Y}{100}$

[0169] The degree of efficacy, expressed in % is denoted. 0% means an efficacy which corresponds to that of the control while an efficacy of 100% means that no disease is observed.

[0170] If the actual fungicidal activity exceeds the calculated value, then the activity of the combination is super-additive, i.e. a synergistic effect exists. In this case, the efficacy which was actually observed must be greater than the value for the expected efficacy (E) calculated from the abovementioned formula.

[0171] A further way of demonstrating a synergistic effect is the method of Tammes (cf “Isoboles, a graphic representation of synergism in pesticides” in Neth. Plant Path., 1964, 70, 73-80).

[0172] The invention is illustrated by the following examples. However the invention is not limited to the examples.

Example: In Vivo Preventive Test on Alternaria Test (Tomatoes)

[0173] Solvent: 24.5 parts by weight of acetone [0174] 24.5 parts by weight of dimethylacetamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0175] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for preventive activity, young plants are sprayed with the preparation of active compound at the stated rate of application. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Alternaria solani. The plants are then placed in an incubation cabinet at approximately 20° C. and a relative atmospheric humidity of 100%.

[0176] The test is evaluated 3 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control while an efficacy of 100% means that no disease is observed. The table below clearly shows that the observed activity of the active compound combination according to the invention is greater than the calculated activity, i.e. a synergistic effect is present.

TABLE-US-00001 TABLE in vivo preventive test on Alternaria test (tomatoes) Application rate of active compound in ppm Efficacy in % Active compounds a.i. found* calc.** (I-3) 2-(difluoromethyl)-N-(3-ethyl-1,1- 1 40 dimethyl-2,3-dihydro-1H-inden-4- 0.5 23 yl)nicotinamide (I-4) 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1- 0.5 40 dimethyl-2,3-dihydro-1H-inden-4- yl]nicotinamide (I-6) 2-(difluoromethyl)-N-[(3R)-1,1- 0.5 0 dimethyl-3-propyl-2,3-dihydro-1H- inden-4-yl]nicotinamide 1.22 flutriafol 1 0 0.5 0 0.25 0 (I-3) + 1.22 2:1  1 + 0.5 50 40 (I-3) + 1.22 1:1 0.5 + 0.5  45 23 (I-4) + 1.22 2:1 0.5 + 0.25 45 40 (I-4) + 1.22 1:1 0.5 + 0.5  65 40 (I-4) + 1.22 1:2 0.5 + 1   45 40 (I-6) + 1.22 2:1 0.5 + 0.25 60 0 *found = activity found **calc. = activity calculated using Colby's formula

TABLE-US-00002 TABLE in vivo preventive test on Alternaria test (tomatoes) Application rate of active compound in ppm Efficacy in % Active compounds a.i. found* calc.** (I-3) 2-(difluoromethyl)-N-(3- 1 0 ethyl-1,1-dimethyl-2,3- dihydro-1H-inden-4- yl)nicotinamide (I-4) 2-(difluoromethyl)-N- 1 40 [(3R)-3-ethyl-1,1- 0.5 15 2,3-dihydro-1H- inden-4-dimethyl- yl]nicotinamide 1.41 prothioconazole 1 15 0.5 15 1.47 tebuconazole 1 15 0.5 8 (I-3) + 1.41 2:1   1 + 0.5 65 15 (I-4) + 1.41 1:1 1 + 1 60 49 (I-4) + 1.47 1:1 0.5 + 0.5 70 21 (I-4) + 1.47 1:2 0.5 + 1   50 28 *found = activity found **calc. = activity calculated using Colby's formula

TABLE-US-00003 TABLE in vivo preventive test on Alternaria test (tomatoes) Application rate of active compound in ppm Efficacy in % Active compounds a.i. found* calc.** (I-6) 2-(difluoromethyl)-N- 1 27 [(3R)-1,1-dimethyl-3- 0.5 30 propyl-2,3-dihydro- 0.25 16 1H-inden-4- yl]nicotinamide 1.41 prothioconazole 0.5 8 1.47 tebuconazole 1 0 0.5 0 0.25 0 (I-6) + 1.41 2:1 1 + 0.5 51 33 (I-6) + 1.47 4:1  1 + 0.25 51 27 (I-6) + 1.47 2:1 1 + 0.5 46 27 (I-6) + 1.47 1:1 0.5 + 0.5   57 30 (I-6) + 1.47 1:4 0.25 + 1   51 16 *found = activity found **calc. = activity calculated using Colby's formula

Example: In Vivo Preventive Blumeria Test (Barley)

[0177] Solvent: 49 parts by weight of N,N-dimethylacetamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0178] To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for preventive activity, young plants are sprayed with the preparation of active compound or active compound combination at the stated rate of application. After the spray coating has been dried, the plants are dusted with spores of Blumeria graminis f.sp. hordei. The plants are placed in the greenhouse at a temperature of approximately 18° C. and a relative atmospheric humidity of approximately 80% to promote the development of mildew pustules.

[0179] The test is evaluated 7 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed. The table below clearly shows that the observed activity of the active compound combination according to the invention is greater than the calculated activity, i.e. a synergistic effect is present.

TABLE-US-00004 TABLE in vivo preventive test on Blumeria test (barley) Application rate of active compound in ppm Efficacy in % Active compounds a.i. found* calc.** (I-6) 2-(difluoromethyl)-N-[(3R)- 50 40 1,1-dimethyl-3-propyl- 25 40 2,3-dihydro-1H-inden- 4-yl]nicotinamide 1.7 difenoconazole 50 60 25 60 (I-6) + 1.7 2:1 50 + 25 90 76 (I-6) + 1.7 1:1 50 + 50 95 76 (I-6) + 1.7 1:2 25 + 50 90 76 *found = activity found **calc. = activity calculated using Colby's formula

TABLE-US-00005 TABLE in vivo preventive test on Blumeria test (barley) Application rate of active compound in ppm Efficacy in % Active compounds a.i. found* calc.** (I-3) 2-(difluoromethyl)-N-(3- 100 57 ethyl-1,1-dimethyl-2,3- 50 29 dihydro-1H-inden-4- 25 0 yl)nicotinamide 1.7 difenoconazole 50 71 25 29 1.12 epoxiconazole 12.5 14 1.30 metconazole 50 93 25 93 1.40 propiconazole 25 43 (I-3) + 1.7 2:1 50 + 25 71 49 (I-3) + 1.7 1:1 25 + 25 71 29 (I-3) + 1.7 1:2 25 + 50 93 71 (I-3) + 1.12 2:1 50 + 25 86 39 (I-3) + 1.12 1:1 25 + 25 100 14 (I-3) + 1.30 2:1 100 + 50  100 97 (I-3) + 1.30 1:1 25 + 25 100 93 (I-3) + 1.30 1:2 25 + 50 100 93 (I-3) + 1.40 2:1 50 + 25 86 59 (I-3) + 1.40 1:1 25 + 25 100 43 *found = activity found **calc. = activity calculated using Colby's formula

TABLE-US-00006 TABLE in vivo preventive test on Blumeria test (barley) Application rate of active compound in ppm Efficacy in % Active compounds a.i. found* calc.** (I-4) 2-(difluoromethyl)-N- 50 0 [(3R)-3-ethyl-1,1- 25 0 dimethyl-2,3- dihydro-1H- inden-4-yl]nicotinamide 1.7 difenoconazole 50 40 25 40 1.12 epoxiconazole 25 30 1.30 metconazole 25 80 1.40 propiconazole 25 80 (I-4) + 1.7 2:1 50 + 25 50 40 (I-4) + 1.7 1:1 25 + 25 50 40 (I-4) + 1.7 1:2 25 + 50 70 40 (I-4) + 1.12 2:1 50 + 25 60 30 (I-4) + 1.30 1:1 25 + 25 100 80 (I-4) + 1.40 2:1 50 + 25 90 80 (I-4) + 1.40 1:1 25 + 25 90 80 *found = activity found **calc. = activity calculated using Colby's formula

Example: In Vivo Preventive Test on Botrytis Test (Beans)

[0180] Solvent: 24.5 parts by weight of acetone [0181] 24.5 parts by weight of dimethylacetamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0182] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for preventive activity, young plants are sprayed with the preparation of active compound. After the spray coating has dried on, 2 small pieces of agar covered with growth of Botrytis cinerea are placed on each leaf. The inoculated plants are placed in a darkened chamber at 20° C. and a relative atmospheric humidity of 100%.

[0183] 2 days after the inoculation, the size of the lesions on the leaves is evaluated. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed. The table below clearly shows that the observed activity of the active compound combination according to the invention is greater than the calculated activity, i.e. a synergistic effect is present.

TABLE-US-00007 TABLE in vivo preventive test on Botrytis test (beans) Application rate of active compound in ppm Efficacy in % Active compounds a.i. found* calc.** (I-5) 2-(difluoromethyl)-N- 1 0 (1,1-dimethyl-3-propyl- 0.5 0 2,3-dihydro-1H-inden-4- yl)nicotinamide (I-6) 2-(difluoromethyl)-N- 0.25 0 [(3R)-1,1-dimethyl-3- propyl-2,3-dihydro-1H- inden-4-yl]nicotinamide 1.22 flutriafol 1 30 0.5 15 0.25 0 (I-5) + 1.22 4:1   1 + 0.25 40 0 (I-5) + 1.22 2:1   1 + 0.5 50 15 (I-5) + 1.22 1:1 1 + 1 43 30 (I-6) + 1.22 1:2 0.5 + 1   50 30 *found = activity found **calc. = activity calculated using Colby's formula

Example: In Vivo Preventive Fusarium graminearum Test (Barley)

[0184] Solvent: 49 parts by weight of N,N-dimethylacetamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0185] To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for preventive activity, young plants are sprayed with the preparation of active compound or active compound combination at the stated rate of application. After the spray coating has been dried, the plants are slightly injured by using a sandblast and afterwards they are sprayed with a conidia suspension of Fusarium graminearum. The plants are placed in the greenhouse under a translucent incubation cabinet at a temperature of approximately 25° C. and a relative atmospheric humidity of approximately 100%.

[0186] The test is evaluated 5 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed. The table below clearly shows that the observed activity of the active compound combination according to the invention is greater than the calculated activity, i.e. a synergistic effect is present.

TABLE-US-00008 TABLE in vivo preventive test on Fusarium graminearum test (barley) Application rate of active compound in ppm Efficacy in % Active compounds a.i. found* calc.** (I-3) 2-(difluoromethyl)-N-(3- 25 0 ethyl-1,1-dimethyl-2,3- dihydro-1H-inden-4- yl)nicotinamide (I-5) 2-(difluoromethyl)-N- 50 29 (1,1-dimethyl-3-propyl- 25 0 2,3-dihydro-1H-inden-4- yl)nicotinamide 1.7 difenoconazole 100 0 50 0 1.12 epoxiconazole 50 0 1.30 metconazole 50 14 (I-3) + 1.12 1:2 25 + 50 43 0 (I-5) + 1.7 1:1 50 + 50 43 29 (I-5) + 1.7 1:2  50 + 100 43 29 (I-5) + 1.30 1:2 25 + 50 57 14 *found = activity found **calc. = activity calculated using Colby's formula

Example: In Vivo Preventive Fusarium nivale (Var. majus) Test (Wheat)

[0187] Solvent: 49 parts by weight of N,N-dimethylacetamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0188] To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for preventive activity, young plants are sprayed with the preparation of active compound or active compound combination at the stated rate of application. After the spray coating has been dried, the plants are slightly injured by using a sandblast and afterwards they are sprayed with a conidia suspension of Fusarium nivale (var. majus). The plants are placed in the greenhouse under a translucent incubation cabinet at a temperature of approximately 10° C. and a relative atmospheric humidity of approximately 100%.

[0189] The test is evaluated 5 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed. The table below clearly shows that the observed activity of the active compound combination according to the invention is greater than the calculated activity, i.e. a synergistic effect is present.

TABLE-US-00009 TABLE in vivo preventive test on Fusarium nivale (var. mains) test (wheat) Application rate of active compound in ppm Efficacy in % Active compounds a.i. found* calc.** (I-4) 2-(difluoromethyl)- 25 13 N-[(3R)-3-ethyl- 12.5 13 1,1-dimethyl-2,3- dihydro-1H-inden-4- yl]nicotinamide 1.7 difenoconazole 12.5 0 1.12 epoxiconazole 12.5 13 (I-4) + 1.7 1:1 12.5 + 12.5 63 13 (I-4) + 1.12 2:1   25 + 12.5 50 23 *found = activity found **calc. = activity calculated using Colby's formula

Example: In Vivo Preventive Leptosphaeria nodorum Test (Wheat)

[0190] Solvent: 49 parts by weight of N,N-dimethylacetamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0191] To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for preventive activity, young plants are sprayed with the preparation of active compound or active compound combination at the stated rate of application. After the spray coating has been dried, the plants are sprayed with a spore suspension of Leptosphaeria nodorum. The plants remain for 48 hours in an incubation cabinet at approximately 20° C. and a relative atmospheric humidity of approximately 100%. The plants are placed in the greenhouse at a temperature of approximately 25° C. and a relative atmospheric humidity of approximately 80%.

[0192] The test is evaluated 8 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed. The table below clearly shows that the observed activity of the active compound combination according to the invention is greater than the calculated activity, i.e. a synergistic effect is present.

TABLE-US-00010 TABLE in vivo preventive test on Leptosphaeria nodorum test (wheat) Application rate of active compound in Efficacy in % Active compounds ppm a.i. found* calc.** (I-3) 2-(difluoromethyl)-N-(3-ethyl-1,1- 100 43 dimethyl-2,3-dihydro-1H-inden-4- 50 14 yl)nicotinamide 25 0 (I-5) 2-(difluoromethyl)-N-(1,1-dimethyl-3- 100 38 propyl-2,3-dihydro-1H-inden-4- 50 38 yl)nicotinamide 1.7 difenoconazole 100 13 50 29 1.40 propiconazole 100 25 (I-3) + 1.7 2:1 100 + 50  71 59 (I-3) + 1.7 1:1 50 + 50 71 39 (I-3) + 1.7 1:2 25 + 50 43 29 (I-5) + 1.7 1:1 100 + 100 50 45 (I-5) + 1.7 1:2  50 + 100 50 45  (I-5) + 1.40 1:1 100 + 100 63 53 *found = activity found **calc. = activity calculated using Colby's formula

TABLE-US-00011 TABLE in vivo preventive test on Leptosphaeria nodorum test (wheat) Application rate of active compound in Efficacy in % Active compounds ppm a.i. found* calc.** (I-4) 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1- 50 0 dimethyl-2,3-dihydro-1H-inden-4- 25 0 yl]nicotinamide (I-6) 2-(difluoromethyl)-N-[(3R)-1,1- 50 14 dimethyl-3-propyl-2,3-dihydro-1H- inden-4-yl]nicotinamide 1.5 cyproconazole 50 0   12.5 0 1.7 difenoconazole 50 43 25 29 1.12 epoxiconazole 50 57 25 43 1.30 metconazole 25 0 (I-4) + 1.5 2:1 .sup. 25 + 12.5 43 0 (I-4) + 1.5 1:1 50 + 50 43 0 (I-4) + 1.7 2:1 50 + 25 86 29 (I-4) + 1.7 1:1 25 + 25 57 29 (I-4) + 1.7 1:2 25 + 50 71 43  (I-4) + 1.12 2:1 50 + 25 57 43  (I-4) + 1.12 1:1 50 + 50 71 57  (I-6) + 1.30 2:1 50 + 25 43 14 *found = activity found **calc. = activity calculated using Colby's formula

Example: In Vivo Preventive Test on Phakopsora Test (Soybeans)

[0193] Solvent: 24.5 parts by weight of acetone [0194] 24.5 parts by weight of dimethylacetamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0195] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for preventive activity, young plants are sprayed with the preparation of active compound at the stated rate of application. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of the causal agent of soybean rust (Phakopsora pachyrhizi) and stay for 24 h without light in an incubation cabinet at approximately 24° C. and a relative atmospheric humidity of 95%. The plants remain in the incubation cabinet at approximately 24° C. and a relative atmospheric humidity of approximately 80% and a day/night interval of 12 h.

[0196] The test is evaluated 7 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed. The table below clearly shows that the observed activity of the active compound combination according to the invention is greater than the calculated activity, i.e. a synergistic effect is present.

TABLE-US-00012 TABLE in vivo preventive test on Phakopsora test (soybeans) Application rate of active compound in Efficacy in % Active compounds ppm a.i. found* calc.** (I-6) 2-(difluoromethyl)-N-[(3R)-1,1- 0.25 60 dimethyl-3-propyl-2,3-dihydro-1H- inden-4-yl]nicotinamide 1.41 prothioconazole 1   15 0.25 0 1.47 tebuconazole 1   0 0.5  0 0.25 0 (I-6) + 1.41 1:1 0.25 + 0.25 65 60 (I-6) + 1.41 1:4 0.25 + 1   85 66 (I-6) + 1.47 1:1 0.25 + 0.25 65 60 (I-6) + 1.47 1:2 0.25 + 0.5  70 60 (I-6) + 1.47 1:4 0.25 + 1   73 60 *found = activity found **calc. = activity calculated using Colby's formula

TABLE-US-00013 TABLE in vivo preventive test on Phakopsora test (soybeans) Application rate of active compound in Efficacy in % Active compounds ppm a.i. found* calc.** (I-3) 2-(difluoromethyl)-N-(3-ethyl-1,1- 1   38 dimethyl-2,3-dihydro-1H-inden-4- yl)nicotinamide (I-4) 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1- 0.5  75 dimethyl-2,3-dihydro-1H-inden-4- 0.25 33 yl]nicotinamide (I-5) 2-(difluoromethyl)-N-(1,1-dimethyl-3- 0.5  78 propyl-2,3-dihydro-1H-inden-4- 0.25 43 yl)nicotinamide 1.41 prothioconazole 1   45 0.5  0 0.25 0 1.47 tebuconazole 1   25 0.5  0 0.25 0 (I-3) + 1.41 4:1   1 + 0.25 73 38 (I-3) + 1.41 2:1 .sup. 1 + 0.5 70 38 (I-3) + 1.41 1:1 1 + 1 93 66 (I-3) + 1.47 4:1   1 + 0.25 65 38 (I-3) + 1.47 2:1 .sup. 1 + 0.5 65 38 (I-3) + 1.47 1:1 1 + 1 85 53 (I-4) + 1.41 1:1 0.5 + 0.5 80 75 (I-4) + 1.41 1:2 0.25 + 0.5  55 33 (I-4) + 1.47 1:2 0.5 + 1.sup.  90 81 (I-4) + 1.47 1:4 0.25 + 1   65 49 (I-5) + 1.41 2:1  0.5 + 0.25 83 78 (I-5) + 1.41 1:1 0.25 + 0.25 50 43 (I-5) + 1.47 2:1  0.5 + 0.25 83 78 (I-5) + 1.47 1:1 0.5 + 0.5 85 78 (I-5) + 1.47 1:2 0.5 + 1.sup.  91 83 (I-5) + 1.47 1:4 0.25 + 1   80 57 *found = activity found **calc. = activity calculated using Colby's formula

TABLE-US-00014 TABLE in vivo preventive test on Phakopsora test (soybeans) Application rate of active compound in Efficacy in % Active compounds ppm a.i. found* calc.** (I-3) 2-(difluoromethyl)-N-(3-ethyl-1,1- 1   84 dimethyl-2,3-dihydro-1H-inden-4- yl)nicotinamide (I-4) 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1- 0.25 65 dimethyl-2,3-dihydro-1H-inden-4- yl]nicotinamide (I-5) 2-(difluoromethyl)-N-(1,1-dimethyl-3- 0.5  89 propyl-2,3-dihydro-1H-inden-4- 0.25 60 yl)nicotinamide (I-6) 2-(difluoromethyl)-N-[(3R)-1,1- 0.25 75 dimethyl-3-propyl-2,3-dihydro-1H- inden-4-yl]nicotinamide 1.22 flutriafol 1   0 0.25 0 (I-3) + 1.22 4:1   1 + 0.25 89 84 (I-4) + 1.22 1:1 0.25 + 0.25 80 65 (I-5) + 1.22 2:1  0.5 + 0.25 94 89 (I-5) + 1.22 1:2 0.5 + 1.sup.  94 89 (I-5) + 1.22 1:4 0.25 + 1   80 60 (I-6) + 1.22 1:1 0.25 + 0.25 83 75 (I-6) + 1.22 1:4 0.25 + 1   83 75 *found = activity found **calc. = activity calculated using Colby's formula

Example: In Vivo Preventive Puccinia triticina Test (Wheat)

[0197] Solvent: 49 parts by weight of N,N-dimethylacetamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0198] To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for preventive activity, young plants are sprayed with the preparation of active compound or active compound combination at the stated rate of application. After the spray coating has been dried, the plants are sprayed with a spore suspension of Puccinia triticina. The plants remain for 48 hours in an incubation cabinet at approximately 20° C. and a relative atmospheric humidity of approximately 100%. The plants are placed in the greenhouse at a temperature of approximately 20° C. and a relative atmospheric humidity of approximately 80%.

[0199] The test is evaluated 8 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed. The table below clearly shows that the observed activity of the active compound combination according to the invention is greater than the calculated activity, i.e. a synergistic effect is present.

TABLE-US-00015 TABLE in vivo preventive test on Puccinia triticina test (wheat) Application rate of active compound in Efficacy in % Active compounds ppm a.i. found* calc.** (I-6) 2-(difluoromethyl)-N-[(3R)-1,1- 25 90 dimethyl-3-propyl-2,3-dihydro-1H- inden-4-yl]nicotinamide 1.7 difenoconazole 50 50 1.12 epoxiconazole   12.5 10 1.40 propiconazole 50 0 (I-6) + 1.7  1:2 25 + 50 100 95 (I-6) + 1.12 2:1 .sup. 25 + 12.5 100 91 (I-6) + 1.40 1:2 25 + 50 100 90 *found = activity found **calc. = activity calculated using Colby's formula

TABLE-US-00016 TABLE in vivo preventive test on Puccinia triticina test (wheat) Application rate of active compound in Efficacy in % Active compounds ppm a.i. found* calc.** (I-4) 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-   12.5 80 dimethyl-2,3-dihydro-1H-inden-4- yl]nicotinamide (I-5) 2-(difluoromethyl)-N-(1,1-dimethyl-3- 25 50 propyl-2,3-dihydro-1H-inden-4-   12.5 30 yl)nicotinamide 1.5 cyproconazole 50 80 25 70 1.7 difenoconazole 25 20   12.5 0 1.12 epoxiconazole 25 40   12.5 30 1.30 metconazole 50 10 25 20   12.5 0 1.40 propiconazole 50 10 25 25 (I-4) + 1.5  1:2 12.5 + 25.sup.  100 94 (I-5) + 1.5  1:2 25 + 50 100 90 (I-4) + 1.7  1:1 12.5 + 12.5 100 80 (I-4) + 1.7  1:2 12.5 + 25.sup.  90 84 (I-5) + 1.12 2:1 .sup. 25 + 12.5 80 65 (I-5) + 1.12 1:1 25 + 25 90 70 (I-5) + 1.12 1:2 12.5 + 25.sup.  80 58 (I-4) + 1.30 1:1 12.5 + 12.5 95 80 (I-4) + 1.30 1:2 12.5 + 25.sup.  90 84 (I-5) + 1.30 1:2 25 + 50 95 55 (I-4) + 1.40 1:2 12.5 + 25.sup.  90 80 (I-5) + 1.40 1:2 25 + 50 100 55 *found = activity found **calc. = activity calculated using Colby's formula

Example: In Vivo Preventive Pyrenophora teres Test (Barley)

[0200] Solvent: 49 parts by weight of N,N-dimethylacetamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0201] To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for preventive activity, young plants are sprayed with the preparation of active compound or active compound combination at the stated rate of application. After the spray coating has been dried, the plants are sprayed with a spore suspension of Pyrenophora teres. The plants remain for 48 hours in an incubation cabinet at approximately 20° C. and a relative atmospheric humidity of approximately 100%. The plants are placed in the greenhouse at a temperature of approximately 20° C. and a relative atmospheric humidity of approximately 80%.

[0202] The test is evaluated 8 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed. The table below clearly shows that the observed activity of the active compound combination according to the invention is greater than the calculated activity, i.e. a synergistic effect is present.

TABLE-US-00017 TABLE in vivo preventive test on Pyrenophora teres test (barley) Application rate of active compound in Efficacy in % Active compounds ppm a.i. found* calc.** (I-3) 2-(difluoromethyl)-N-(3-ethyl-1,1- 100  50 dimethyl-2,3-dihydro-1H-inden-4- 50 38 yl)nicotinamide 25 13 1.5 cyproconazole 100  0 25 25 1.7 difenoconazole 50 13 1.40 propiconazole 100  25 50 13 (I-3) + 1.5 2:1 50 + 25 75 53 (I-3) + 1.5 1:2 100 + 100 94 50 (I-3) + 1.5 1:2  50 + 100 75 38 (I-3) + 1.7 2:1 100 + 50  75 56 (I-3) + 1.7 1:1 50 + 50 50 45  (I-3) + 1.40 2:1 100 + 50  75 56  (I-3) + 1.40 1:2  50 + 100 63 53 *found = activity found **calc. = activity calculated using Colby's formula

TABLE-US-00018 TABLE in vivo preventive test on Pyrenophora teres test (barley) Application rate of active compound in Efficacy in % Active compounds ppm a.i. found* calc.** (I-4) 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1- 50 33 dimethyl-2,3-dihydro-1H-inden-4- 25 22 yl]nicotinamide 12.5 22 (I-5) 2-(difluoromethyl)-N-(1,1-dimethyl-3- 50 0 propyl-2,3-dihydro-1H-inden-4- 25 0 yl)nicotinamide 1.5 cyproconazole 50 25 25 22 1.7 difenoconazole 12.5 22 1.40 propiconazole 50 25 25 22 (I-4) + 1.5 1:1 25 + 25 56 40 (I-5) + 1.5 1:2 25 + 50 50 25 (I-4) + 1.7 2:1   25 + 12.5 56 40  (I-4) + 1.40 2:1 50 + 25 67 48  (I-5) + 1.40 1:1 50 + 50 50 25 *found = activity found **calc. = activity calculated using Colby's formula

Example: In Vivo Preventive Septoria tritici Test (Wheat)

[0203] Solvent: 49 parts by weight of N,N-dimethylacetamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0204] To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for preventive activity, young plants are sprayed with the preparation of active compound or active compound combination at the stated rate of application. After the spray coating has been dried, the plants are sprayed with a spore suspension of Septoria tritici. The plants remain for 48 hours in an incubation cabinet at approximately 20° C. and a relative atmospheric humidity of approximately 100% and afterwards for 60 hours at approximately 15° C. in a translucent incubation cabinet at a relative atmospheric humidity of approximately 100%. The plants are placed in the greenhouse at a temperature of approximately 15° C. and a relative atmospheric humidity of approximately 80%.

[0205] The test is evaluated 21 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed. The table below clearly shows that the observed activity of the active compound combination according to the invention is greater than the calculated activity, i.e. a synergistic effect is present.

TABLE-US-00019 TABLE in vivo preventive test on Septoria tritici test (wheat) Application rate of active compound in Efficacy in % Active compounds ppm a.i. found* calc.** (I-4) 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1- 50 75 dimethyl-2,3-dihydro-1H-inden-4- 25 75 yl]nicotinamide 1.5 cyproconazole 50 50 1.12 epoxiconazole 50 63 (I-4) + 1.5 1:1 50 + 50 94 88 (I-4) + 1.5 1:2 25 + 50 94 88  (I-4) + 1.12 1:1 50 + 50 100 91 *found = activity found **calc. = activity calculated using Colby's formula

TABLE-US-00020 TABLE in vivo preventive test on Septoria tritici test (wheat) Application rate of active compound in Efficacy in % Active compounds ppm a.i. found* calc.** (I-3) 2-(difluoromethyl)-N-(3-ethyl-1,1- 100 83 dimethyl-2,3-dihydro-1H-inden-4- 50 83 yl)nicotinamide 25 17 (I-6) 2-(difluoromethyl)-N-[(3R)-1,1- 50 75 dimethyl-3-propyl-2,3-dihydro-1H- inden-4-yl]nicotinamide 1.5 cyproconazole 100 17 1.7 difenoconazole 50 0 1.12 epoxiconazole 50 33 25 0 1.30 metconazole 50 33 25 17 1.40 propiconazole 100 38 50 0 25 0 (I-3) + 1.5  1:1 100 + 100 100 86 (I-3) + 1.5  1:2  50 + 100 100 86 (I-3) + 1.7  1:2 25 + 50 67 17 (I-3) + 1.12 2:1 50 + 25 92 83 (I-3) + 1.12 1:1 25 + 25 67 17 (I-3) + 1.12 1:2 25 + 50 83 44 (I-3) + 1.30 1:1 25 + 25 50 31 (I-3) + 1.30 1:2 25 + 50 50 44 (I-3) + 1.40 1:1 25 + 25 67 17 (I-3) + 1.40 1:2 25 + 50 83 17 (I-6) + 1.40 1:2  50 + 100 94 84 *found = activity found **calc. = activity calculated using Colby's formula

Example: In Vivo Preventive Test on Sphaerotheca Test (Cucumbers)

[0206] Solvent: 24.5 parts by weight of acetone [0207] 24.5 parts by weight of dimethylacetamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0208] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for preventive activity, young plants are sprayed with the preparation of active compound at the stated rate of application. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of Sphaerotheca fuliginea. The plants are then placed in a greenhouse at approximately 23° C. and a relative atmospheric humidity of approximately 70%.

[0209] The test is evaluated 7 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed. The table below clearly shows that the observed activity of the active compound combination according to the invention is greater than the calculated activity, i.e. a synergistic effect is present.

TABLE-US-00021 TABLE in vivo preventive test on Sphaerotheca test (cucumbers) Application rate of active compound in Efficacy in % Active compounds ppm a.i. found* calc.** (I-3) 2-(difluoromethyl)-N-(3-ethyl-1,1- 0.5 0 dimethyl-2,3-dihydro-1H-inden-4- yl)nicotinamide 1.22 flutriafol 1   24 (I-3) + 1.22 1:2 0.5 + 1 51 24 *found = activity found **calc. = activity calculated using Colby's formula

Example: In Vivo Preventive Test on Uromyces Test (Beans)

[0210] Solvent: 24.5 parts by weight of acetone [0211] 24.5 parts by weight of dimethylacetamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0212] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for preventive activity, young plants are sprayed with the preparation of active compound at the stated rate of application. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of the causal agent of bean rust (Uromyces appendiculatus) and then remain for 1 day in an incubation cabinet at approximately 20° C. and a relative atmospheric humidity of 100%.

[0213] The plants are then placed in a greenhouse at approximately 21° C. and a relative atmospheric humidity of approximately 90%. The test is evaluated 10 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed.

TABLE-US-00022 TABLE in vivo preventive test on Uromyces test (beans) Application rate of active compound in Efficacy in % Active compounds ppm a.i. found* calc.** (I-3) 2-(difluoromethyl)-N-(3-ethyl-1,1- 0.25 90 dimethyl-2,3-dihydro-1H-inden-4- yl)nicotinamide (I-5) 2-(difluoromethyl)-N-(1,1-dimethyl-3- 0.5  95 propyl-2,3-dihydro-1H-inden-4- yl)nicotinamide 1.41 prothioconazole 1   0 0.25 0 1.47 tebuconazole 1   0 0.5  0 0.25 0 (I-3) + 1.41 1:4 0.25 + 1    98 90 (I-3) + 1.47 1:2 0.25 + 0.5  95 90 (I-5) + 1.41 2:1 0.5 + 0.25 100 95 (I-5) + 1.47 2:1 0.5 + 0.25 100 95 (I-5) + 1.47 1:2 0.5 + 1   100 95 *found = activity found **calc. = activity calculated using Colby's formula

Example: In Vivo Preventive Test on Venturia Test (Apples)

[0214] Solvent: 24.5 parts by weight of acetone [0215] 24.5 parts by weight of dimethylacetamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0216] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. To test for preventive activity, young plants are sprayed with the preparation of active compound at the stated rate of application. After the spray coating has dried on, the plants are inoculated with an aqueous conidia suspension of the causal agent of apple scab (Venturia inaequalis) and then remain for 1 day in an incubation cabinet at approximately 20° C. and a relative atmospheric humidity of 100%. The plants are then placed in a greenhouse at approximately 21° C. and a relative atmospheric humidity of approximately 90%.

[0217] The test is evaluated 10 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed. The table below clearly shows that the observed activity of the active compound combination according to the invention is greater than the calculated activity, i.e. a synergistic effect is present.

TABLE-US-00023 TABLE in vivo preventive test on Venturia test (apples) Application rate of active compound in Efficacy in % Active compounds ppm a.i. found* calc.** (I-4) 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1- 1 37 dimethyl-2,3-dihydro-1H-inden-4- yl]nicotinamide 1.41 prothioconazole 1 0 (I-4) + 1.41 1:1 1 + 1 88 37 *found = activity found **calc. = activity calculated using Colby's formula

TABLE-US-00024 TABLE in vivo preventive test on Venturia test (apples) Application rate of active compound in Efficacy in % Active compounds ppm a.i. found* calc.** (I-3) 2-(difluoromethyl)-N-(3-ethyl-1,1- 1 11 dimethyl-2,3-dihydro-1H-inden-4- yl)nicotinamide (I-4) 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1- 1 87 dimethyl-2,3-dihydro-1H-inden-4-   0.5 16 yl]nicotinamide 1.22 flutriafol 1 8   0.5 0   0.25 0 (I-3) + 1.22 4:1 .sup. 1 + 0.25 83 11 (I-3) + 1.22 2:1  1 + 0.5 91 11 (I-3) + 1.22 1:1 1 + 1  93 18 (I-4) + 1.22 4:1 .sup. 1 + 0.25 87 94 (I-4) + 1.22 2:1 0.5 + 0.25 85 16 (I-4) + 1.22 1:1 0.5 + 0.5  50 16 (I-4) + 1.22 1:2 0.5 + 0.25 46 23 *found = activity found **calc. = activity calculated using Colby's formula