Active substance combinations that have nematicidal, insecticidal, and fungicidal properties and are based on trifluorobutenyl compounds

Abstract

Disclosed are novel active substance combinations comprising specific heterocyclic trifluorobutenyls and previously known fungicidal agents. Said active substance combinations have a very good synergistic fungicidal, nematicidal, insecticidal, and/or acaricidal effect.

Claims

1. A synergistic combination comprising: (a) one or more active compounds of the formula (I) ##STR00015## in which X represents halogen and n represents 0, 1 or 2, and (b) one or more active compounds from group (b3): (b3) climbazole, clotrimazole, imazalil, oxpoconazole, triflumizole, azaconazole, bromuconazole, cyproconazole, diclobutrazol, diniconazole, diniconazole-M, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, furconazole, furconazole-cis, hexaconazole, imibenconazole, metconazole, myclobutanil, penconazole, propiconazole, quinconazole, simeconazole, tetraconazole, triadimefon, uniconazole and uniconazole-P.

2. The combination of claim 1, characterized in that it comprises one or more compounds of the formula (I) in which X represents fluorine, chlorine or bromine and n represents 0 or 2.

3. The combination of claim 1, characterized in that it comprises one or more compounds of the formula (I) in which X represents fluorine or chlorine and n represents 2.

4. The combination of claim 1, wherein said one or more active compounds of the formula (I) is one of the following compounds of the formulae (IA), (IB) and (IC): ##STR00016##

5. The combination of claim 4, wherein said one or more active compounds of the formula (I) is any compound of the formula (IC).

6. A method for controlling fungi, nematodes, insects or acarids, wherein the combination of claim 1 is contacted with nematodes, insects, fungi and/or their habitats.

7. A method for controlling fungi, nematodes, insects or acarids, wherein the combination of claim 2 is contacted with nematodes, insects, fungi and/or their habitats.

8. A method for controlling fungi, nematodes, insects or acarids, wherein the combination of claim 3 is contacted with nematodes, insects, fungi and/or their habitats.

9. A method for controlling fungi, nematodes, insects or acarids, wherein the combination of claim 4 is contacted with nematodes, insects, fungi and/or their habitats.

10. A method for controlling fungi, nematodes, insects or acarids, wherein the combination of claim 5 is contacted with nematodes, insects, fungi and/or their habitats.

11. A process for preparing fungicidal, nematicidal, insecticidal and/or fungicidal compositions, characterized in that combinations as claimed in claim 1 are mixed with extenders and/or surfactants.

12. A process for preparing fungicidal, nematicidal, insecticidal and/or fungicidal compositions, characterized in that combinations as claimed in claim 2 are mixed with extenders and/or surfactants.

13. A process for preparing fungicidal, nematicidal, insecticidal and/or fungicidal compositions, characterized in that combinations as claimed in claim 3 are mixed with extenders and/or surfactants.

14. A process for preparing fungicidal, nematicidal, insecticidal and/or fungicidal compositions, characterized in that combinations as claimed in claim 4 are mixed with extenders and/or surfactants.

15. A process for preparing fungicidal, nematicidal, insecticidal and/or fungicidal compositions, characterized in that combinations as claimed in claim 5 are mixed with extenders and/or surfactants.

16. A composition comprising the combination of claim 1 and extenders and/or surfactants.

17. A composition comprising the combination of claim 2 and extenders and/or surfactants.

18. A composition comprising the combination of claim 3 and extenders and/or surfactants.

19. A composition comprising the combination of claim 4 and extenders and/or surfactants.

20. A composition comprising the combination of claim 5 and extenders and/or surfactants.

Description

EXAMPLES

Example A

Meloidogyene Test (Nematicidal Action)

(1) Solvent: 7 parts by weight of dimethylformamide

(2) Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

(3) 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.

(4) Vessels are filled with sand, solution of active compound, Meloidogyne incognita egg/larvae suspension and lettuce seeds. The lettuce seeds germinate and plants develop. On the roots, galls are formed.

(5) After the desired period of time, the nematicidal action is determined in % by the formation of galls. 100% means that no galls have been found; 0% means that the number of galls on the treated plants corresponds to that of the untreated control. The determined kill rates are inserted into Colby's formula.

(6) In this test, the following active compound combinations according to the present application showed a synergistically enhanced activity compared to the active compounds applied on their own (found*=activity found in the test; calc. **=activity calculated according to Colby):

(7) TABLE-US-00003 TABLE 3 (IC) + prothioconazole Active compound Active compound concentration [ppm] Kill rate [%] after 14 days (IC) 0.8 50 prothioconazole 20 50 (IC) + prothioconazole 0.8 + 20 found*: 80 (1:25) calc.**: 75

(8) TABLE-US-00004 TABLE 4 (IC) + fludioxonil Active compound Active compound concentration [ppm] Kill rate [%] after 14 days (IC) 0.8 50 fludioxonil 20 0 (IC) + fludioxonil 0.8 + 20 found*: 90 (1:25) calc.**: 50

(9) TABLE-US-00005 TABLE 5 (IC) + trifloxystrobin Active compound Active compound concentration [ppm] Kill rate [%] after 14 days (IC) 0.8 50 trifloxystrobin 20 0 (IC) + trifloxystrobin 0.8 + 20 found*: 60 (1:25) calc.**: 50

Example B

Plutella Test, Sensitive Strain (Insecticidal Action)

(10) Solvent: 7 parts by weight of dimethylformamide

(11) Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

(12) 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 emulsifier-containing water to the desired concentration.

(13) Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and are populated with caterpillars of the diamondback moth (Plutella xylostella, sensitive strain) while the leaves are still moist. After the desired period of time, the kill in % is determined. 100% means that all caterpillars have been killed; 0% means that none of the caterpillars have been killed. The determined kill rates are inserted into Colby's formula.

(14) In this test, the following active compound combination in accordance with the present application showed a synergistically enhanced activity compared to the active compounds applied on their own (found*=activity found in the test; calc.**=activity calculated according to Colby):

(15) TABLE-US-00006 TABLE 6 (IC) + trifloxystrobin Active compound Active compound concentration [ppm] Kill rate [%] after 3 days (IC) 100 0 trifloxystrobin 100 15 (IC) + trifloxystrobin 100 + 100 found*: 55 (1:1) calc.**: 15

Example C

Mycelium Growth Test

(16) Nutrient medium: 39 parts by weight of potato dextrose agar

(17) 5 parts by weight of agar agar

(18) These are dissolved in 1000 ml of distilled water and autoclaved at 121° C. for 30 minutes.

(19) Solvent: 49 parts by weight of acetone

(20) Emulsifier: 1 part by weight of alkylaryl polyelycol ether

(21) 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 required stock solution concentration. To establish the test concentration, in each case 1 part by volume of the active compound stock solution is thoroughly mixed with 9 parts by volume of liquid nutrient medium and poured into Petri dishes. Once the nutrient medium has cooled and solidified, the plates are inoculated with the microorganisms listed in the table below and incubated at about 20° C.

(22) Depending on the growth rate of the microorganisms, evaluation is carried out after 2 to 8 days. 0% means an efficacy which corresponds to that of the control, whereas an efficacy of 100% means that no mycelium growth is observed.

(23) The tables below clearly show that the found activity of the active compound combination according to the invention is higher than the calculated activity, i.e. a synergistic effect is present.

(24) TABLE-US-00007 TABLE 7 mycelium growth test with Phytophthora cactorum (IC) + pencycuron Active compound concentration in the Active compound nutrient medium [ppm] Efficacy [%] (IC) 100 18 pencycuron 200  0 (IC) + pencycuron 100 + 200 actual efficacy: 58 (1:2) expected value calculated according to Colby: 18

(25) TABLE-US-00008 TABLE 8 mycelium growth test with Phytophthora cactorum (IC) + fosetyl-A1 Active compound concentration in the Active compound nutrient medium [ppm] Efficacy [%] (IC)  50  7 fosetyl-A1 100 34 (IC) + fosetyl-A1 50 + 100 actual efficacy: 58 (1:2) expected value calculated according to Colby: 39

(26) TABLE-US-00009 TABLE 9 mycelium growth test with Phytophthora cactorum (IC) + tolylfluanid Active compound concentration in the Active compound nutrient medium [ppm] Efficacy [%] (IC) 100 23 tolylfluanid  10 65 (IC) + tolylfluanid 100 + 10 actual efficacy: 92 (1:2) expected value calculated according to Colby: 73

(27) TABLE-US-00010 TABLE 10 mycelium growth test with Phytophthora cactorum (IC) + trifloxystrobin Active compound concentration in the Active compound nutrient medium [ppm] Efficacy [%] (IC) 100 23 trifloxystrobin  10 29 (IC) + trifloxystrobin 100 + 10 actual efficacy: 65 (10:1) expected value calculated according to Colby: 45

(28) TABLE-US-00011 TABLE 11 mycelium growth test with Phytophthora cactorum (IC) + fluoxastrobin Active compound concentration in the Active compound nutrient medium [ppm] Efficacy [%] (IC) 50  7 fluoxastrobin  5 28 (IC) + fluoxastrobin 50 + 5 actual efficacy: 58 (10:1) expected value calculated according to Colby: 33

(29) TABLE-US-00012 TABLE 12 mycelium growth test with Phytophthora cactorum (IC) + tebuconazole Active compound concentration in the Active compound nutrient medium [ppm] Efficacy [%] (IC) 100 23 tebuconazole 100 12 (IC) + tebuconazole 100 + 100 actual efficacy: 88 (1:1) expected value calculated according to Colby: 32

(30) TABLE-US-00013 TABLE 13 mycelium growth test with Phytophthora cactorum (IC) + prochloraz Active compound concentration in the Active compound nutrient medium [ppm] Efficacy [%] (IC) 100 18 prochloraz  50 30 (IC) + prochloraz 100 + 50 actual efficacy: 85 (2:1) expected value calculated according to Colby: 43

(31) TABLE-US-00014 TABLE 14 mycelium growth test with Fusarium nivale (IC) + fosetyl-A1 Active compound concentration in the Active compound nutrient medium [ppm] Efficacy [%] (IC)  1 15 fosetyl-A1 10 45 (IC) + fosetyl-A1 1 + 10 actual efficacy: 73 (1:10) expected value calculated according to Colby: 53

(32) TABLE-US-00015 TABLE 15 mycelium growth test with Rhizoctonia solani (IC) + fosetyl-A1 Active compound concentration in the Active compound nutrient medium [ppm] Efficacy [%] (IC)  1  0 fosetyl-A1 10 12 (IC) + fosetyl-A1 1 + 10 actual efficacy: 77 (1:10) expected value calculated according to Colby: 12

(33) TABLE-US-00016 TABLE 16 mycelium growth test with Rhizoctonia solani (IC) + trifloxystrobin Active compound concentration in the Active compound nutrient medium [ppm] Efficacy [%] (IC) 10 49 trifloxystrobin  1 39 (IC) + trifloxystrobin 10 + 1 Actual efficacy: 86 (10:1) expected value calculated according to Colby: 69

(34) TABLE-US-00017 TABLE 17 mycelium growth test with Rhizoctonia solani (IC) + fluoxastrobin Active compound concentration in the Active compound nutrient medium [ppm] Efficacy [%] (IC) 10 49 fluoxastrobin  1 39 (IC) + fluoxastrobin 10 + 1 actual efficacy: 80 (10:1) expected value calculated according to Colby: 69

(35) TABLE-US-00018 TABLE 18 mycelium growth test with Phythium ultimum (IC) + iprodione Active compound concentration in the Active compound nutrient medium [ppm] Efficacy [%] (IC) 100 11 iprodione 200  9 (IC) + iprodione 100 + 200 actual efficacy: 84 (1:2) expected value calculated according to Colby: 19

(36) TABLE-US-00019 TABLE 19 mycelium growth test with Phythium ultimum (IC) + tolylfluanid Active compound concentration in the Active compound nutrient medium [ppm] Efficacy [%] (IC) 100 11 tolylfluanid  10 82 (IC) + tolylfluanid 100 + 10 actual efficacy: 99 (10:1) expected value calculated according to Colby: 84

(37) TABLE-US-00020 TABLE 20 mycelium growth test with Phythium ultimum (IC) + fluoxastrobin Active compound concentration in the Active compound nutrient medium [ppm] Efficacy [%] (IC) 100 31 fluoxastrobin  10 74 (IC) + fluoxastrobin 100 + 10 actual efficacy: 93 (1:2) expected value calculated according to Colby: 82

(38) TABLE-US-00021 TABLE 21 mycelium growth test with Phythium ultimum (IC) + tebuconazole Active compound concentration in the Active compound nutrient medium [ppm] Efficacy [%] (IC) 100 11 tebuconazole 100 72 (IC) + tebuconazole 100 + 100 actual efficacy: 86 (1:1) expected value calculated according to Colby: 75