Active compound combinations having insecticidal/acaricidal properties

Abstract

The present invention relates to novel active compound combinations comprising at least one known compound of the formula (I) ##STR00001##
and at least one further active compound, which combinations are highly suitable for controlling animal and microbial pests such as unwanted insects and/or unwanted acarida and/or unwanted nematodes.

Claims

1. An active compound combination comprising at least one compound of formula (I) ##STR00008## and at least one active compound of group (II) which is selected from the group consisting of (II-1) abamectin, (II-2) emamectin benzoate, (II-4) milbemectin, (II-6) spiromesifen, (II-7) spirotetramat, (II-8) cyenopyrafen, (II-9) cyflumetofen, (II-10) spinosad and (II-14) pyflubumide, or is selected from the group consisting of a compound of formula (IIa) ##STR00009## and a compound of formula (IIb) ##STR00010## wherein the compound combination is synergistically active; and wherein the mixing ratio of active compound of the formula (I) to (II-10) spinosad is 10:1 to 1:10 based on weight ratio; the mixing ratios of active compound of the formula (I) to (II-1) abamectin, to (II-2) emamectin benzoate and to (II-4) milbemectin are 400:1 to 1:1, 50:1 to 1:1 and 5:1 to 1:5, respectively, each based on weight ratio; the mixing ratios of active compound of the formula (I) to (II-6) spiromesifen and to (II-7) spirotetramat are 20:1 to 1:10 and 30:1 to 1:30, respectively, each based on weight ratio; the mixing ratios of active compound of the formula (I) to (II-8) cyenopyrafen, to (II-9) cyflumetofen and to (II-14) pyflubumide are 10:1 to 1:10, 10:1 to 1:5 and 20:1 to 1:10, respectively, each based on weight ratio; and the mixing ratio of active compound of the formula (I) to compounds of formula (IIa) or (IIb) is 10:1 to 1:10, based on weight ratio.

2. The active compound combination according to claim 1, wherein the compound of formula (I) is present in form of a (+) enantiomer, or is present in form of a mixture of (+) enantiomer and (−) enantiomer which is enriched in the (+) enantiomer.

3. The active compound combination according to claim 2, wherein the compound of formula (I) is present in the form of a mixture of (+) enantiomer and (−) enantiomer which is enriched in the (+) enantiomer in a mixing ratio of at least 60:40 (+):(−) enantiomer.

4. A product comprising the active compound combination as defined in claim 1 for controlling one or more animal pests.

5. The product according to claim 4, wherein the animal pest is an insect, arachnid or acarid pest.

6. A product comprising the active compound combination as defined in claim 1 for controlling one or more microbial pests.

7. A product comprising the active compound combination as defined in claim 1 for controlling nematodes.

8. A product comprising the active compound combination as defined in claim 1 as a plant-strengthening agent.

9. A product comprising an active compound combination as defined in claim 1 for seed treatment.

10. A product comprising the active compound combination as defined in claim 1 on one or more transgenic plants.

11. A product comprising the active compound combination according to claim 1 for treating one or more plants or parts thereof selected from the group consisting of citrus, pome fruits, stone fruits, tropical fruits, nuts, berries, vegetables, cotton, soybean, grape, tea, coffee, maize, rice and ornamentals.

12. A method for controlling animal or microbial pests, comprising allowing the active compound combination as defined in claim 1 to act on animal or microbial pests and/or a habitat thereof.

13. The method according to claim 12, wherein the animal pest is an insect or arachnid or acarid pest.

14. A process for preparing a crop protection agent, comprising mixing the active compound combination as defined in claim 1 with one or more extenders and/or surfactants.

Description

EXAMPLES

(1) Formula for the Efficacy of the Combination of Two Compounds

(2) The expected efficacy of a given combination of two compounds is calculated as follows (see Colby, S. R., “Calculating Synergistic and antagonistic Responses of Herbicide Combinations”, Weeds 15, pp. 20-22, 1967): If X is the efficacy expressed in % mortality of the untreated control for test compound A at a concentration of m ppm respectively m g/ha, Y is the efficacy expressed in % mortality of the untreated control for test compound B at a concentration of n ppm respectively n g/ha, E is the efficacy expressed in % mortality of the untreated control using the mixture of A and B at m and n ppm respectively m and n g/ha, then is

(3) $E=X+Y-\frac{X\times Y}{100}$ If the observed insecticidal efficacy of the combination is higher than the one calculated as “E”, then the combination of the two compounds is more than additive, i.e. there is a synergistic effect.

Example A

(4) Myzus persicae Spray Test

(5) Solvent: 78.0 parts by weight acetone 1.5 parts by weight dimethylformamide Emulsifier: alkylarylpolyglycol ether

(6) To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvents and is diluted with water, containing an emulsifier concentration of 1000 ppm, to the desired concentration. To produce a suitable preparation of a spore suspension the spores are diluted with emulsifier containing water to the desired concentration. Further test concentrations are prepared by dilution with emulsifier containing water.

(7) Chinese cabbage (Brassica pekinensis) leaf disks infected with all instars of the green peach aphid (Myzus persicae), are sprayed with a preparation of the active ingredient of the desired concentration.

(8) After the specified period of time, mortality in % is determined. 100% means all aphids have been killed; 0% means none of the aphids have been killed. The mortality values determined thus are recalculated using the Colby-formula (see above).

(9) According to the present application in this test e.g. the following combinations showed a synergistic effect in comparison to the single compounds:

(10) TABLE-US-00002 TABLE A Myzus persicae - spray test Efficacy Concentration in % after Active Ingredient in g ai/ha 6 days Compound (Cpd) of formula (I) 8 0 2 0 Cyenopyrafen 2 0 0.5 0 obs.* cal.** Cpd of formula (I) + Cyenopyrafen 8 + 2   70 0 (4:1) (4:1) according to the invention 2 + 0.5 70 0 Compound (Cpd) of formula (IIa) 16 0 obs.* cal.** Cpd of formula (I) + Cpd of formula 8 + 16  70 0 (IIa) (1:2) according to the invention *obs. = observed insecticidal efficacy, **cal. = efficacy calculated with Colby-formula

Example B

(11) Tetranychus urticae—Spray Test OP-Resistant

(12) Solvent: 78.0 parts by weight acetone 1.5 parts by weight dimethylformamide Emulsifier: alkylarylpolyglycol ether

(13) To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvents and is diluted with water, containing an emulsifier concentration of 1000 ppm, to the desired concentration. To produce a suitable preparation of a spore suspension the spores are diluted with emulsifier containing water to the desired concentration. Further test concentrations are prepared by dilution with emulsifier containing water.

(14) French bean (Phaseolus vulgaris) leaf disks infected with all instars of the two spotted spidermite (Tetranychus urticae), are sprayed with a preparation of the active ingredient of the desired concentration.

(15) After the specified period of time, mortality in % is determined. 100% means all spider mites have been killed and 0% means none of the spider mites have been killed. The mortality values determined thus are recalculated using the Colby-formula (see above).

(16) According to the present application in this test e.g. the following combinations showed a synergistic effect in comparison to the single compounds:

(17) TABLE-US-00003 TABLE B-1 Tetranychus urticae - spray test Efficacy Concentration in % after Active Ingredient in g ai/ha 2 days Cpd of formula (I) 0.5 0  0.125 0 Abamectin   0.00125 0 obs.* cal.** Cpd of formula (I) + Abamectin (400:1)   0.5 + 0.00125 70  0 according to the invention (Cpd) of formula (IIa) 1   0 obs.* cal.** Cpd of formula (I) + Cpd of formula (IIa) (1:2) 0.5 + 1   70  0 according to the invention (Cpd) of formula (IIb) 0.5 0 obs.* cal.** Cpd of formula (I) + Cpd of formula (IIb) (1:1) 0.5 + 0.5  70  0 according to the invention Cyflumetofen 0.5 0 obs.* cal.** Cpd of formula (I) + Cyflumetofen (1:1) 0.5 + 0.5  90  0 according to the invention Emamectin-benzoate   0.0125 0    0.003125 0 obs.* cal.** Cpd of formula (I) + Emamectin-benzoate (40:1)  0.5 + 0.0125 70  0 (40:1) according to the invention  0.125 + 0.003125 70  0 Pyflubumide   0.0125 0 obs.* cal.** Cpd of formula (I) + Pyflubumide (10:1) 0.125 + 0.0125 70  0 according to the invention  0.125 0 Spinosad   0.03125 0 obs.* cal.** Cpd of formula (I) + Spinosad (4:1)  0.5 + 0.125 90  0 according to the invention  0.125 + 0.03125 70  0 Spiromesifen  0.05 0 obs.* cal.** Cpd of formula (I) + Spiromesifen (10:1) 0.5 + 0.05 90  0 according to the invention Spirotetramat  0.05 0 obs.* cal.** Cpd of formula (I) + Spirotetramat (10:1) 0.5 + 0.05 70  0 according to the invention

(18) TABLE-US-00004 TABLE B-2 Tetranychus urticae - spray test Efficacy Concentration in % after Active Ingredient in g ai/ha 6 days Cpd of formula (I) 0.6  0 0.5  0 0.3  0  0.125  0 Abamectin  0.03 70  0.015 70 obs.* obs.* cal.** Cpd of formula (I) + Abamectin (20:1) 0.6 + 0.03 100   70 (20:1)  0.3 + 0.015 100   70 according to the invention Cpd of formula (IIa) 1   0 obs.* cal.** Cpd of formula (I) + Cpd of formula (IIa) (1:2) 0.5 + 1   90 0 according to the invention Cpd of formula (IIb) 0.5 0 obs.* cal.** Cpd of formula (I) + Cpd of formula (IIb) (1:1) 0.5 + 0.5  70 0 according to the invention Cyenopyrafen  0.125 0 obs.* cal.** Cpd of formula (I) + Cyenopyrafen (4:1)  0.5 + 0.125 70 0 according to the invention Cyflumetofen 0.5 0 obs.* cal.** Cpd of formula (I) + Cyflumetofen (1:1) 0.5 + 0.5  90 0 according to the invention Emamectin-benzoate  0.15 0   0.0125 0    0.003125 0 obs.* cal.** Cpd of formula (I) + Emamectin-benzoate (4:1) 0.6 + 0.15 90 0 (40:1)  0.5 + 0.0125 70 0 (40:1) according to the invention  0.125 + 0.003125 70 0 Milbemectin 1.5 0  0.75 0 obs.* cal.** Cpd of formula (I) + Milbemectin (1:2.5) 0.6 + 1.5  90 0 (1:2.5) according to the invention 0.3 + 0.75 70 0 Pyflubumide 0.6 70    0.0125 0 obs.* cal.** Cpd of formula (I) + Pyflubumide (1:1) 0.6 + 0.6  100  70  (10:1) according to the invention 0.125 + 0.0125 90 0 Spinosad  0.125 0   0.03125 0  0.5 + 0.125 obs.* cal.** Cpd of formula (I) + Spinosad (4:1)  0.125 + 0.03125 90 0 according to the invention 70 0 Spiromesifen 0.6 0  0.05 0 obs.* cal.** Cpd of formula (I) + Spiromesifen (1:1) 0.6 + 0.6  70 0 (10:1) according to the invention 0.5 + 0.05 90 0 Spirotetramat  0.05 0 obs.* cal.** Cpd of formula (I) + Spirotetramat 0.5 + 0.05 90 0 (10:1) according to the invention *obs. = observed insecticidal efficacy, **cal. = efficacy calculated with Colby-formula

Example C

(19) Tetranychus urticae Spray Test; OP-Resistant

(20) Solvent: 7 parts by weight of dimethylformamide

(21) Emulsifier: alkylaryl polyglycol ether

(22) To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and is diluted with water, containing an emulsifier concentration of 1000 ppm, to the desired concentration. Further test concentrations are prepared by dilution with emulsifier containing water.

(23) Bean plants (Phaseolus vulgaris) which are heavily infested with all stages of the two-spotted spider mite (Tetranychus urticae) are treated by being sprayed with the preparation of the active compound of the desired concentration.

(24) After the specified period of time mortality in % is determined. 100% means all the spider mites have been killed and 0% means none of the spider mites have been killed. The mortality values determined thus are recalculated using the Colby-formula (see above).

(25) According to the present application in this test e.g. the following combinations showed a synergistic effect in comparison to the single compounds:

(26) TABLE-US-00005 TABLE C-1 Tetranychus urticae - spray test Efficacy Concentration in % after Active Ingredient in ppm 3 days Cpd of formula (I) 0.4 0 Abamectin 0.01 0 obs.* cal.** Cpd of formula (I) + Abamectin 0.4 + 0.01 40  0 (40:1) according to the invention

(27) TABLE-US-00006 TABLE C-2 Tetranychus urticae - spray test Efficacy Concentration in % after Active Ingredient in ppm 7 days Cpd of formula (I) 0.8 30 Spirotetramat 2 40 obs.* cal.** Cpd of formula (I) + Spirotetramat 0.8 + 2 90 58 (1:2.5) according to the invention *obs. = observed insecticidal efficacy, **cal. = efficacy calculated with Colby-formula

Example D

(28) Meloidogyne incognita—Test

(29) Solvent: 125.0 parts by weight of acetone

(30) To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, and the concentrate is diluted with water to the desired concentration. To produce a suitable preparation of a spore suspension the spores are diluted with water to the desired concentration.

(31) Vessels are filled with sand, a solution of the active ingredient, a suspension containing eggs and larvae of the southern root-knot nematode (Meloidogyne incognita) and salad seeds. The salad seeds germinate and the seedlings grow. Galls develop in the roots.

(32) After the specified period of time nematicidal activity is determined on the basis of the percentage of gall formation. 100% means no galls were found and 0% means the number of galls found on the roots of the treated plants was equal to that in untreated control plants.

(33) According to the present application in this test e.g. the following combinations showed a synergistic effect in comparison to the single compounds:

(34) TABLE-US-00007 TABLE D Meloidogyne incognita - test Efficacy Concentration in % after Active Ingredient in ppm 14 days Cpd of formula (I) 2 70  1 0 Spirotetramat 60 0 30 0 obs.* cal.** Cpd of formula (I) + Spirotetramat 2 + 60 100  70 (1:30) according to the invention 1 + 30 70  0 *obs. = observed insecticidal efficacy, **cal. = efficacy calculated with Colby-formula