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. A 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 III.

2. Combination according to claim 1 comprising at least one compound of formula (I) wherein 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 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 (1.3) azoxystrobin (131860-33-8), (1.7) dimoxystrobin (141600-52-4), (1.12) fluoxastrobin (361377-29-9), (1.13) kresoxim-methyl (143390-89-0), (1.14) metominostrobin (133408-50-1), (1.16) picoxystrobin (117428-22-5), (1.17) pyraclostrobin (175013-18-0).

5. A 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. A composition for controlling phytopathogenic harmful fungi, comprising a content of one combination according to claim 1, in addition to one or more extenders and/or surfactants.

7. A 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 one or more plant growth regulators.

10. A 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

[0163] 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.

[0164] 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

[0165] X is the efficacy when active compound A is applied at an application rate of m ppm (or g/ha), [0166] Y is the efficacy when active compound B is applied at an application rate of n ppm (or g/ha), [0167] 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]$E=X+Y-\frac{X.Math.Y}{100}$

[0168] 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.

[0169] 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.

[0170] 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).

[0171] 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)

[0172] Solvent: 24.5 parts by weight of acetone [0173] 24.5 parts by weight of dimethylacetamide [0174] 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.

[0176] 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%.

[0177] 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.

[0178] 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 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 (I-6) 2-(difluoromethyl)-N-[(3R)-1,1- 1 27 dimethyl-3-propyl-2,3-dihydro-1H- 0.5 30 inden-4-yl]nicotinamide 1.3 azoxystrobin 1 65 0.5 35 0.25 45 1.16 picoxystrobin 1 50 0.5 30 0.25 30 1.22 trifloxystrobin 1 35 0.5 24 0.25 8 (I-3) + 1.3 4:1   1 + 0.25 75 70 (I-3) + 1.3 2:1   1 + 0.5 88 64 (I-3) + 1.3 1:1 0.5 + 0.5 80 64 (I-3) + 1.3 1:2 0.25 + 0.5  75 45 (I-3) + 1.3 1:4 0.25 + 1   83 70 (I-3) + 1.16 4:1   1 + 0.25 73 62 (I-3) + 1.16 2:1   1 + 0.5 75 62 (I-3) + 1.16 1:1 0.5 + 0.5 80 62 (I-3) + 1.16 1:2 0.25 + 0.5  50 41 (I-3) + 1.16 1:4 0.25 + 1   78 58 (I-4) + 1.3 2:1   1 + 0.5 89 71 (I-4) + 1.3 1:1 0.5 + 0.5 73 55 (I-4) + 1.3 1:2 0.5 + 1   86 76 (I-6) + 1.22 4:1   1 + 0.25 68 33 (I-6) + 1.22 2:1  0.5 + 0.25 51 45 (I-6) + 1.22 1:1 0.5 + 0.5 65 47 (I-6) + 1.22 1:2 0.5 + 1   70 54 *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-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 1.3 azoxystrobin 1 15 0.5 8 0.25 35 1.16 picoxystrobin 1 35 0.5 8 0.25 8 (I-5) + 1.3 4:1   1 + 0.25 55 45 (I-5) + 1.3 2:1   1 + 0.5 70 21 (I-5) + 1.3 1:1 1 + 1 85 28 (I-5) + 1.3 1:2 0.5 + 1   70 21 (I-5) + 1.3 1:4 0.25 + 1   70 15 (I-5) + 1.16 4:1   1 + 0.25 50 21 (I-5) + 1.16 2:1  0.5 + 0.25 50 14 (I-5) + 1.16 1:1 1 + 1 63 45 (I-5) + 1.16 1:2 0.5 + 1   73 40 (I-5) + 1.16 1:4 0.25 + 1   60 35 (I-6) + 1.3 4:1   1 + 0.25 78 64 (I-6) + 1.3 2:1   1 + 0.5 83 49 (I-6) + 1.3 1:1 1 + 1 83 53 (I-6) + 1.3 1:2 0.5 + 1   83 34 (I-6) + 1.3 1:4 0.25 + 1   63 28 (I-6) + 1.16 4:1   1 + 0.25 65 49 (I-6) + 1.16 2:1   1 + 0.5 60 49 (I-6) + 1.16 1:1 0.25 + 0.25 60 21 (I-6) + 1.16 1:4 0.25 + 1   55 45 *found = activity found **calc. = activity calculated using Colby's formula

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

[0179] Solvent: 24.5 parts by weight of acetone [0180] 24.5 parts by weight of dimethylacetamide [0181] 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.

[0183] 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%.

[0184] 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.

[0185] 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-00003 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 (I-4) 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1- 0.5 15 dimethyl-2,3-dihydro-1H-inden-4- yl]nicotinamide 1.3 azoxystrobin 0.5 15 0.25 30 1.16 picoxystrobin 0.5 40 0.25 40 (I-3) + 1.3 4:1   1 + 0.25 50 30 (I-3) + 1.3 2:1  0.5 + 0.25 50 33 (I-3) + 1.3 1:1 0.5 + 0.5 50 18 (I-3) + 1.3 1:2 0.25 + 0.5  50 15 (I-3) + 1.16 4:1   1 + 0.25 50 40 (I-3) + 1.16 2:1   1 + 0.5 53 40 (I-3) + 1.16 1:1 0.5 + 0.5 50 42 (I-3) + 1.16 1:2 0.25 + 0.5  50 40 (I-4) + 1.3 1:1 0.5 + 0.5 45 28 *found = activity found **calc. = activity calculated using Colby's formula

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

[0186] Solvent: 24.5 parts by weight of acetone [0187] 24.5 parts by weight of dimethylacetamide [0188] Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0189] 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.

[0190] 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%.

[0191] 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.

[0192] 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.

[0193] 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 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- 0.5 87 yl]nicotinamide 0.25 35 1.3 azoxystrobin 0.5 18 0.25 0 1.16 picoxystrobin 1 9 0.5 24 0.25 0 (I-3) + 1.3 2:1  0.5 + 0.25 79 71 (I-3) + 1.3 1:2 0.25 + 0.5  68 37 (I-3) + 1.16 1:1 0.25 + 0.25 44 24 (I-3) + 1.16 1:2 0.25 + 0.5  62 42 (I-3) + 1.16 1:4 0.25 + 1   74 30 (I-4) + 1.3 4:1   1 + 0.25 100 87 (I-4) + 1.3 2:1   1 + 0.5 97 89 (I-4) + 1.3 1:1 0.25 + 0.25 76 35 (I-4) + 1.16 1:1 1 + 1 97 88 (I-4) + 1.16 1:2 0.5 + 1   94 88 *found = activity found **calc. = activity calculated using Colby's formula

TABLE-US-00005 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-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- 1 93 dimethyl-3-propyl-2,3-dihydro-1H- 0.5 92 inden-4-yl]nicotinamide 0.25 95 1.3 azoxystrobin 0.5 41 0.25 16 1.16 picoxystrobin 1 62 0.5 0 0.25 0 (I-5) + 1.3 4:1 1 + 0.25 92 82 (I-5) + 1.3 2:1 0.5 + 0.25   93 86 (I-5) + 1.3 1:1 1 + 0.25 97 88 (I-5) + 1.16 4:1 1 + 0.25 97 85 (I-5) + 1.16 2:1 1 + 0.5  96 85 (I-5) + 1.16 1:1 1 + 1   99 94 (I-5) + 1.16 1:2 0.25 + 0.5    85 78 (I-6) + 1.3 2:1 0.5 + 0.25   100 93 (I-6) + 1.3 1:1 0.5 + 0.5   100 95 (I-6) + 1.16 2:1 1 + 0.5  99 93 (I-6) + 1.16 1:1 0.5 + 0.5   99 92 *found = activity found **calc. = activity calculated using Colby's formula

TABLE-US-00006 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- 1 38 dimethyl-2,3-dihydro-1H-inden-4- 0.5 28 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- 0.25 43 propyl-2,3-dihydro-1H-inden-4- yl)nicotinamide (I-6) 2-(difluoromethyl)-N-[(3R)-1,1- 0.25 60 dimethyl-3-propyl-2,3-dihydro-1H- inden-4-yl]nicotinamide 1.22 trifloxystrobin 1 0 0.5 0 0.25 0 (I-3) + 1.22 4:1   1 + 0.25 73 38 (I-3) + 1.22 2:1   1 + 0.5 68 38 (I-3) + 1.22 1:1 1 + 1 83 38 (I-3) + 1.22 1:2 0.5 + 1   55 28 (I-4) + 1.22 1:1 0.5 + 0.5 85 75 (I-4) + 1.22 1:4 0.25 + 1   50 33 (I-5) + 1.55 1:1 0.25 + 0.25 48 43 (I-6) + 1.22 1:1 0.25 + 0.25 70 60 (I-6) + 1.22 1:4 0.25 + 1   83 60 *found = activity found **calc. = activity calculated using Colby's formula

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

[0194] Solvent: 24.5 parts by weight of acetone [0195] 24.5 parts by weight of dimethylacetamide [0196] Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0197] 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%. The plants are then placed in a greenhouse at approximately 21° C. and a relative atmospheric humidity of approximately 90%.

[0198] 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-00007 TABLE in vivo preventive test on Uromyces 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- 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- 0.25 93 yl)nicotinamide 1.22 trifloxystrobin 1 0 0.25 0 (I-3) + 1.22 1:1 0.25 + 0.25 95 90 (I-3) + 1.22 1:4 0.25 + 1   95 90 (I-5) + 1.22 1:1 0.25 + 0.25 100 93 (I-5) + 1.22 1:2 0.5 + 1   100 95 (I-5) + 1.22 1:4 0.25 + 1   98 93 *found = activity found **calc. = activity calculated using Colby's formula

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

[0199] Solvent: 24.5 parts by weight of acetone [0200] 24.5 parts by weight of dimethylacetamide [0201] Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0202] 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.

[0203] 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%.

[0204] The plants are then placed in a greenhouse at approximately 21° C. and a relative atmospheric humidity of approximately 90%.

[0205] 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.

[0206] 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 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- 1 13 dimethyl-2,3-dihydro-1H-inden-4- 0.5 11 yl)nicotinamide 0.25 10 (I-4) 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1- 1 21 dimethyl-2,3-dihydro-1H-inden-4- 0.5 12 yl]nicotinamide 0.25 10 1.3 azoxystrobin 1 30 0.5 25 (I-3) + 1.3 2:1   1 + 0.5 47 35 (I-3) + 1.3 1:1 1 + 1 76 39 (I-3) + 1.3 1:2 0.5 + 1   73 38 (I-3) + 1.3 1:4 0.25 + 1   53 37 (I-4) + 1.3 2:1   1 + 0.5 71 41 (I-4) + 1.3 1:1 1 + 1 66 45 (I-4) + 1.3 1:2 0.5 + 1   64 38 (I-4) + 1.3 1:4 0.25 + 1   62 37 *found = activity found **calc. = activity calculated using Colby's formula

TABLE-US-00009 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-5) 2-(difluoromethyl)-N-(1,1-dimethyl-3- 1 15 propyl-2,3-dihydro-1H-inden-4- 0.25 0 yl)nicotinamide (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 1.3 azoxystrobin 1 94 0.5 88 1.16 picoxystrobin 0.5 13 (I-5) + 1.3 2:1 1 + 0.5 99 90 (I-5) + 1.3 1:2 0.25 + 0.5   94 88 (I-6) + 1.3 2:1 1 + 0.5 95 90 (I-6) + 1.3 1:2 0.25 + 0.5   93 88 (I-6) + 1.3 1:4 0.25 + 1   100 94 (I-6) + 1.16 2:1 1 + 0.5 60 22 *found = activity found **calc. = activity calculated using Colby's formula

TABLE-US-00010 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- 1 15 dimethyl-2,3-dihydro-1H-inden-4- yl)nicotinamide (I-4) 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1- 1 37 dimethyl-2,3-dihydro-1H-inden-4- yl]nicotinamide (I-5) 2-(difluoromethyl)-N-(1,1-dimethyl-3- 1 10 propyl-2,3-dihydro-1H-inden-4- yl)nicotinamide 1.22 trifloxystrobin 1 5 0.5 5 0.25 0 (I-3) + 1.22 1:1 1 + 1   50 19 (I-4) + 1.22 4:1 1 + 0.25 65 37 (I-5) + 1.22 2:1 1 + 0.5  61 15 *found = activity found **calc. = activity calculated using Colby's formula