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 respiratory chain at complex I or II.

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 respiratory chain at complex I or II, optionally (1.001) bixafen, (1.002) boscalid, (1.006) fluopyram, (1.008) fluxapyroxad, (1.011) isopyrazam (mixture of syn-epimeric racemate 1RS,4SR,9RS and anti-epimeric racemate 1RS,4SR,9SR), (1.012) isopyrazam (anti-epimeric racemate 1RS,4SR,9SR), (1.013) isopyrazam (anti-epimeric enantiomer 1R,4S,9S), (1.014) isopyrazam (anti-epimeric enantiomer 1S,4R,9R), (1.015) isopyrazam (syn-epimeric racemate 1RS,4SR,9RS), (1.016) iso-pyrazam (syn-epimeric enantiomer 1R,4S,9R), (1.017) isopyrazam (syn-epimeric enantiomer 1S,4R,9S), (1.020) penflufen, (1.021) penthiopyrad, (1.022) sedaxane, (1.029) benzovindiflupyr, (1.077) N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide.

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

[0157] 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.

[0158] 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

[0159] X is the efficacy when active compound A is applied at an application rate of m ppm (or g/ha), [0160] Y is the efficacy when active compound B is applied at an application rate of n ppm (or g/ha), [0161] 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]$E=X+Y-\frac{X.Math.Y}{100}$

[0162] 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.

[0163] 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.

[0164] A further way of demonstrating a synergistic effect is the method of Tammes (cf. “Isoboles, a graphic representation of synergism in pesticides” in Neth. J. Plant Path., 1964, 70, 73-80).

[0165] 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)

[0166]

TABLE-US-00001 Solvent: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide Emulsifier:   1 part by weight of alkylaryl polyglycol ether

[0167] 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%.

[0168] 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-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-ethyl-1,1- 1 45 dimethyl-2,3-dihydro-1H-inden-4- 0.5 45 yl)nicotinamide 0.25 15 (I-4) 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1- 1 55 dimethyl-2,3-dihydro-1H-inden-4- 0.5 30 yl]nicotinamide 0.25 23 1.008 fluxapyroxad 1 55 0.25 15 1.032 3-(difluoromethyl)-1-methyl-N-(1,1,3- 1 15 trimethyl-2,3-dihydro-1H-inden-4-yl)- 0.5 0 1H-pyrazole-4-carboxamide 0.25 15 (I-3) + 1.008 1:1 0.25 + 0.25 45 28 (I-3) + 1.032 1:1 0.5 + 0.5 60 45 (I-4) + 1.008 2:1  0.5 + 0.25 70 41 (I-4) + 1.008 1:1 1 + 1 88 80 (I-4) + 1.008 1:2 0.5 + 1   80 69 (I-4) + 1.008 1:4 0.25 + 1   75 65 (I-4) + 1.032 4:1   1 + 0.25 85 62 (I-4) + 1.032 2:1 1 0.5 65 55 (I-4) + 1.032 1:1 1 + 1 75 62 (I-4) + 1.032 1:2 0.5 + 1   65 41 (I-4) + 1.032 1:4 0.25 + 1   70 34 (I-5) 2-(difluoromethyl)-N-(1,1-dimethyl-3- 1 15 propyl-2,3-dihydro-1H-inden-4- 0.5 8 yl)nicotinamide 0.25 0 (I-6) 2-(difluoromethyl)-N-[(3R)-1,1- 1 45 dimethyl-3-propyl-2,3-dihydro-1H- 0.5 23 inden-4-yl]nicotinamide 0.25 15 1.008 fluxapyroxad 1 78 0.5 45 0.25 8 1.032 3-(difluoromethyl)-1-methyl-N-(1,1,3- 1 8 trimethyl-2,3-dihydro-1H-inden-4-yl)- 0.5 0 1H-pyrazole-4-carboxamide 0.25 0 (I-5) + 1.008 4:1   1 + 0.25 60 21 (I-5) + 1.008 2:1   1 + 0.5 78 53 (I-5) + 1.008 1:1 0.5 + 0.5 70 49 (I-5) + 1.008 1:2 0.25 + 0.5  68 45 (I-5) + 1.008 1:4 0.25 + 1   83 78 (I-5) + 1.032 1:1 1 + 1 45 21 (I-5) + 1.032 1:2 0.5 + 1   50 14 (I-6) + 1.008 4:1   1 + 0.25 73 49 (I-6) + 1.008 2:1 0.5 0.25 65 28 (I-6) + 1.008 1:1 0.5 + 0.5 75 57 (I-6) + 1.008 1:2 0.25 + 0.5  78 53 (I-6) + 1.032 4:1   1 + 0.25 55 45 (I-6) + 1.032 2:1   1 + 0.5 60 45 (I-6) + 1.032 1:1 0.5 + 0.5 55 23 (I-6) + 1.032 1:2 0.5 + 1   65 28 (I-6) + 1.032 1:4 0.25 + 1   55 21 *found = activity found **calc. = activity calculated using Colby's formula

Example: In Vivo Preventive Blumeria Test (Barley)

[0169]

TABLE-US-00003 Solvent: 49 parts by weight of N,N-dimethylacetamide Emulsifier:  1 part by weight of alkylaryl polyglycol ether

[0170] 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.

[0171] 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-3) 2-(difluoromethyl)-N-(3-ethyl-1,1- 100  57 dimethyl-2,3-dihydro-1H-inden-4- 50 29 yl)nicotinamide 1.006 fluopyram 100  71 50 29 (I-3) + 1.006 2:1 100 + 50  86 69 (I-3) + 1.006 1:1 50 + 50 71 49 (I-3) + 1.006 1:2  50 + 100 93 80 (I-4) 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1- 25 0 dimethyl-2,3-dihydro-1H-inden-4- yl]nicotinamide 1.006 fluopyram 50 0 (I-4) + 1.006 1:2 25 + 50 50 0 (I-6) 2-(difluoromethyl)-N-[(3R)-1,1- 50 40 dimethyl-3-propyl-2,3-dihydro-1H- inden-4-yl]nicotinamide 1.006 fluopyram 50 80 (I-6) + 1.006 1:1 50 + 50 95 88 *found = activity found **calc. = activity calculated using Colby's formula

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

[0172]

TABLE-US-00005 Solvent: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide Emulsifier:   1 part by weight of alkylaryl polyglycol ether

[0173] 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%.

[0174] 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-00006 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-3) 2-(difluoromethyl)-N-(3-ethyl-1,1- 1 0 dimethyl-2,3-dihydro-1H-inden-4- 0.5 4 yl)nicotinamide 0.25 0 1.008 fluxapyroxad 1 8 0.5 15 1.032 3-(difluoromethyl)-1-methyl-N-(1,1,3- 1 14 trimethyl-2,3-dihydro-1H-inden-4-yl)- 0.5 0 1H-pyrazole-4-carboxamide 0.25 18 (I-3) + 1.008 2:1   1 + 0.5 45 15 (I-3) + 1.008 1:1 1 + 1 45 8 (I-3) + 1.032 4:1   1 + 0.25 50 18 (I-3) + 1.032 2:1 1 0.5 45 0 (I-3) + 1.032 1:1 1 + 1 50 14 (I-3) + 1.032 1:2 0.5 + 1   50 17 (I-3) + 1.032 1:4 0.25 + 1   45 14 (I-5) 2-(difluoromethyl)-N-(1,1-dimethyl-3- 1 0 propyl-2,3-dihydro-1H-inden-4- yl)nicotinamide (I-6) 2-(difluoromethyl)-N-[(3R)-1,1- 1 0 dimethyl-3-propyl-2,3-dihydro-1H- 0.5 0 inden-4-yl]nicotinamide 0.25 0 1.008 fluxapyroxad 1 0 0.5 0 1.032 3-(difluoromethyl)-1-methyl-N-(1,1,3- 1 0 trimethyl-2,3-dihydro-1H-inden-4-yl)- 1H-pyrazole-4-carboxamide (I-5) + 1.008 2:1   1 + 0.5 51 0 (I-5) + 1.008 1:1 1 + 1 43 0 (I-6) + 1.008 2:1   1 + 0.5 59 0 (I-6) + 1.008 1:1 1 + 1 59 0 (I-6) + 1.008 1:2 0.25 + 0.5  60 0 (I-6) + 1.032 1:2 0.5 + 1   66 0 *found = activity found **calc. = activity calculated using Colby's formula

Example: In Vivo Preventive Leptosphaeria nodorum Test (Wheat)

[0175]

TABLE-US-00007 Solvent: 49 parts by weight of N,N-dimethylacetamide Emulsifier:  1 part by weight of alkylaryl polyglycol ether

[0176] 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%.

[0177] 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-00008 TABLE in vivo preventive test on Leptosphaeria nodorum test (wheat) Application rate of active compound in ppm Efficacy in % Active compounds a.i. found* calc.** (I-4) 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1- 25 0 dimethyl-2,3-dihydro-1H-inden-4- yl]nicotinamide 1.006 fluopyram 25 14 12.5 14 (I-4) + 1.006 2:1 25 + 12.5 43 14 (I-4) + 1.006 1:1 25 + 25   43 14 *found = activity found **calc. = activity calculated using Colby's formula

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

[0178]

TABLE-US-00009 Solvent: 24.5 parts by weight of acetone 24.5 parts by weight of dimethylacetamide Emulsifier:   1 part by weight of alkylaryl polyglycol ether

[0179] 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.

[0180] 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-00010 TABLE in vivo preventive test on Phakopsora test (soybeans) Application rate of active compound in ppm Efficacy in % Active compounds a.i. found* calc.** (I-3) 2-(difluoromethyl)-N-(3-ethyl-1,1- 0.5 71 dimethyl-2,3-dihydro-1H-inden-4- 0.25 24 yl)nicotinamide (I-4) 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1- 1 87 dimethyl-2,3-dihydro-1H-inden-4- 0.25 35 yl]nicotinamide 1.008 fluxapyroxad 1 0 0.5 0 0.25 9 1.032 3-(difluoromethyl)-1-methyl-N-(1,1,3- 1 0 trimethyl-2,3-dihydro-1H-inden-4-yl)- 0.5 0 1H-pyrazole-4-carboxamide 0.25 0 (I-3) + 1.008 1:1 0.5 + 0.5 76 71 (I-3) + 1.032 1:1 0.5 + 0.5 91 71 (I-3) + 1.032 1:2 0.5 + 1   87 71 (I-3) + 1.032 1:4 0.25 + 1   74 24 (I-4) + 1.008 4:1   1 + 0.25 99 88 (I-4) + 1.008 2:1   1 + 0.5 99 87 (I-4) + 1.008 1:1 0.25 + 0.25 71 41 (I-4) + 1.008 1:4 0.25 + 1   75 34 (I-4) + 1.032 2:1 1 0.5 94 87 (I-4) + 1.032 1:1 0.25 + 0.25 81 35 (I-4) + 1.032 1:2 0.25 + 0.5  74 35 (I-4) + 1.032 1:4 0.25 + 1   53 35 (I-5) 2-(difluoromethyl)-N-(1,1-dimethyl-3- 1 85 propyl-2,3-dihydro-1H-inden-4- 0.5 84 yl)nicotinamide 0.25 78 (I-6) 2-(difluoromethyl)-N-[(3R)-1,1- 0.5 92 dimethyl-3-propyl-2,3-dihydro-1H- inden-4-yl]nicotinamide 1.008 fluxapyroxad 0.5 0 0.25 0 1.032 3-(difluoromethyl)-1-methyl-N-(1,1,3- 0.25 0 trimethyl-2,3-dihydro-1H-inden-4-yl)- 1H-pyrazole-4-carboxamide (I-5) + 1.008 4:1   1 + 0.25 95 85 (I-5) + 1.008 2:1  0.5 + 0.25 92 84 (I-5) + 1.008 1:1 0.25 + 0.25 91 78 (I-5) + 1.008 1:2 0.25 + 0.5  92 78 (I-5) + 1.032 4:1   1 + 0.25 96 85 (I-5) + 1.032 2:1  0.5 + 0.25 95 84 (I-5) + 1.032 1:1 0.25 + 0.25 95 78 (I-6) + 1.032 2:1  0.5 + 0.25 97 92 *found = activity found **calc. = activity calculated using Colby's formula

Example: In Vivo Preventive Puccinia Triticina Test (Wheat)

[0181]

TABLE-US-00011 Solvent: 49 parts by weight of N,N-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 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%.

[0183] 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-00012 TABLE in vivo preventive test on Puccinia triticina test (wheat) Application rate of active compound in ppm Efficacy in % Active compounds 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- yl)nicotinamide 1.006 fluopyram 50 10 12.5 0 (I-4) + 1.006 1:1 12.5 + 12.5 90 80 (I-5) + 1.006 1:2 25 + 50 95 55 (I-6) 2-(difluoromethyl)-N-[(3R)-1,1- 25 90 dimethyl-3-propyl-2,3-dihydro-1H- inden-4-yl]nicotinamide 1.006 fluopyram 50 30 (I-6) + 1.006 1:2 25 + 50 100 93 *found = activity found **calc. = activity calculated using Colby's formula

Example: In Vivo Preventive Pyrenophora Teres Test (Barley)

[0184]

TABLE-US-00013 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 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%.

[0186] 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-00014 TABLE in vivo preventive test on Pyrenophora teres test (barley) Application rate of active compound in ppm Efficacy in % Active compounds 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 (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- 100 50 propyl-2,3-dihydro-1H-inden-4- 50 0 yl)nicotinamide 25 0 1.006 fluopyram 50 75 12.5 33 (I-3) + 1.006 2:1 100 + 50  100 88 (I-3) + 1.006 1:1 50 + 50 100 84 (I-3) + 1.006 1:2 25 + 50 94 78 (I-4) + 1.006 2:1   25 + 12.5 56 48 (I-4) + 1.006 1:1 12.5 + 12.5 56 48 (I-4) + 1.006 1:2 25 + 50 89 83 (I-5) + 1.006 2:1 100 + 50  94 88 (I-5) + 1.006 1:1 50 + 50 88 75 (I-5) + 1.006 1:2 25 + 50 88 75 *found = activity found **calc. = activity calculated using Colby's formula

Example: In Vivo Preventive Septoria tritici Test (Wheat)

[0187]

TABLE-US-00015 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 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%.

[0189] 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-00016 TABLE in vivo preventive test on Septoria tritici test (wheat) Application rate of active compound in ppm Efficacy in % Active compounds a.i. found* calc.** (I-3) 2-(difluoromethyl)-N-(3-ethyl-1,1- 50 83 dimethyl-2,3-dihydro-1H-inden-4- 25 17 yl)nicotinamide 1.006 fluopyram 25 17 (I-3) + 1.006 2:1 50 + 25 100 86 (I-3) + 1.006 1:1 25 + 25 67 31 *found = activity found **calc. = activity calculated using Colby's formula

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

[0190]

TABLE-US-00017 Solvent: 24.5 parts by weight of acetone 24.5 parts by weight of 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 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%.

[0192] 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-00018 TABLE in vivo preventive test on Venturia test (apples) Application rate of active compound in ppm Efficacy in % Active compounds a.i. found* calc.** (I-3) 2-(difluoromethyl)-N-(3-ethyl-1,1- 0.5 11 dimethyl-2,3-dihydro-1H-inden-4- yl)nicotinamide (I-4) 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1- 1 21 dimethyl-2,3-dihydro-1H-inden-4- 0.5 12 yl]nicotinamide 1.008 fluxapyroxad 1 20 0.5 8 1.032 3-(difluoromethyl)-1-methyl-N-(1,1,3- 1 26 trimethyl-2,3-dihydro-1H-inden-4-yl)- 1H-pyrazole-4-carboxamide (I-3) + 1.008 1:2 0.5 + 1   46 29 (I-4) + 1.008 2:1   1 + 0.5 52 27 (I-4) + 1.008 1:2 0.5 + 1   46 29 (I-4) + 1.032 1:1 1 + 1 68 42 (I-5) 2-(difluoromethyl)-N-(1,1-dimethyl-3- 1 15 propyl-2,3-dihydro-1H-inden-4- 0.5 0 yl)nicotinamide 0.25 0 (I-6) 2-(difluoromethyl)-N-[(3R)-1,1- 1 10 dimethyl-3-propyl-2,3-dihydro-1H- 0.5 5 inden-4-yl]nicotinamide 0.25 0 1.008 fluxapyroxad 1 55 0.5 10 1.032 3-(difluoromethyl)-1-methyl-N-(1,1,3- 1 0 trimethyl-2,3-dihydro-1H-inden-4-yl)- 0.5 0 1H-pyrazole-4-carboxamide (I-5) + 1.008 1:1 1 + 1 90 62 (I-5) + 1.008 1:2 0.5 + 1   94 55 (I-5) + 1.032 1:1 1 + 1 45 15 (I-5) + 1.032 1:2 0.5 + 1   43 0 (I-5) + 1.032 1:4 0.25 + 1   57 0 (I-6) + 1.008 2:1   1 + 0.5 93 19 (I-6) + 1.008 1:1 1 + 1 94 60 (I-6) + 1.008 1:2 0.5 + 1   63 57 (I-6) + 1.008 1:4 0.25 + 1   80 55 (I-6) + 1.032 2:1   1 + 0.5 42 10 (I-6) + 1.032 1:2 0.5 + 1   58 5 *found = activity found **calc. = activity calculated using Colby's formula