Fungicidal compositions

Abstract

A fungicidal composition comprising a mixture of components (A) and (B), wherein components (A) and (B) are as defined in claim 1, and use of the compositions in agriculture or horticulture for controlling or preventing infestation of plants by phytopathogenic microorganisms, preferably fungi.

Claims

1. A fungicidal composition comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is the compound of formula (I): ##STR00004## or an agrochemically acceptable salt, N-oxide, diastereoisomer, enantiomer or tautomer thereof; and component (B) is pydiflumetofen, wherein the weight ratio of (A) to (B) is from 10:1 to 1:10, and wherein components (A) and (B) are present in a synergistically effective weight ratio.

2. The composition according to claim 1, wherein component (A) is the compound of Formula (IA): ##STR00005## or an agrochemically acceptable salt, N-oxide or tautomer thereof.

3. The composition according to claim 1, wherein the weight ratio of (A) to (B) is from 5:1 to 1:5.

4. The composition according to claim 1, further comprising an agriculturally acceptable carrier and/or formulation adjuvant, and optionally, a surfactant.

5. A fungicidal composition according to claim 1, wherein the composition comprises an additional active ingredient component (C), which is different to component (B), selected from the group consisting of: benzovindiflupyr, isopyrazam, azoxystrobin, difenoconazole, prothioconazole, chlorothalonil, fenpropidin, acibenzolar-S-methyl, cyproconazole, cyprodinil, fenpropimorph, propiconazole, hexaconazole, penconazole, pyrifenox, fludioxonil, pyroquilon, tricyclazole, fluazinam, mandipropamid, metalaxyl, metalaxyl-M, oxadixyl, oxathiapiprolin, paclobutrazol, sulfur, thiabendazole, Aspergillus Flavus NRRL 21882 and Bacillus subtilis var. amyloliquefaciens Strain FZB24.

6. A method of controlling diseases on useful plants or on propagation material thereof caused by phytopathogens, which comprises applying to the useful plants, the locus thereof or propagation material thereof, a composition as defined in claim 1.

7. The method according to claim 6, wherein the phytophathogen is from a genus selected from the group consisting of Septoria, Mycosphaerella, Pyricularia, Pyrenophora, Colletotrichum, Uncinula, Venturia, Ramularia, Erysiphe, Puccinia and Phakopsora.

8. The method according to claim 6, wherein the phytophathogen is selected from the group consisting of Septoria tritici, Septoria glycines, Septoria nodorum, Mycosphaerella arachidis, Mycosphaerella fijiensis, Pyricularia oryzae, Pyrenophora teres, Colletotrichum lagenarium, Venturia inaequalis and Ramularia collo-cygni.

9. The method according to claim 6, wherein the useful plant is selected from the group consisting of cereals, legumes, vegetables, fruits, and nuts.

10. The method according to claim 6, wherein the useful plant is selected from the group consisting of wheat, barley, rice, soybean, apples, grapes, cucumber, peanuts, and bananas.

11. The method according to claim 6, wherein the components (A) and (B) are applied in a sequential manner.

12. A method of protecting natural substances of plant and/or animal origin, which have been taken from the natural life cycle, and/or their processed forms, which comprises applying to said natural substances of plant and/or animal origin or their processed forms a combination of components (A) and (B) as defined in claim 1.

13. The method according to claim 6, wherein the phytophathogen is selected from the group consisting of Pyricularia oryzae or Mycosphaerella arachidis.

14. A fungicidal composition comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is the compound of formula (I): ##STR00006## or an agrochemically acceptable salt, N-oxide, diastereoisomer, enantiomer or tautomer thereof; and component (B) is pydiflumetofen, wherein the weight ratio of (A) to (B) is from 4:1 to 1:4.

Description

BIOLOGICAL EXAMPLES

(1) The compositions according to the invention are tested for their biological (fungicidal) activity as dimethylsulfoxide (DMSO) solutions using one or more of the following protocols (Examples 2 to 8). A standard description of the liquid culture tests is provided in Example 1.

(2) The compound of component (A) which is (1S)-2,2-bis(4-fluorophenyl)-1-methylethyl N-{[3-(acetyloxy)-4-methoxy-2-pyridyl]carbonyl}-L-alaninate (florylpicoxamid—CAS registry no. 1961312-55-9) and its synthesis are known from WO 2016/122802. As already indicated, component (B) of the compositions are known and are commercially available and/or can be prepared using procedures known in the art and/or procedures reported in the literature.

Example 1

Liquid Culture Tests in Well Plates

(3) Mycelia fragments or conidia suspensions of a fungus, prepared either freshly from liquid cultures of the fungus or from cryogenic storage, are directly mixed into nutrient broth. DMSO solutions of the test compound (max. 10 mg/mL) is diluted with 0.025% Tween20 by factor 50 and 10 μL of this solution is pipetted into a microtiter plate (96-well format). The nutrient broth containing the fungal spores/mycelia fragments is then added to give an end concentration of the tested compound. The test plates are incubated in the dark at 24° C. and 96% relative humidity (rh). The inhibition of fungal growth is determined photometrically and visually after 3-7 days, depending on the pathosystem, and percent antifungal activity relative to the untreated check is calculated.

Example 2

Glomerella lagenarium (Syn. Colletotrichum lagenarium, Anthracnose of Cucurbits)

(4) Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). After placing a DMSO solution of the test compositions into a microtiter plate (96-well format), the nutrient broth containing the fungal spores was added. The test plates were incubated at 24° C. and the inhibition of growth was determined photometrically after 72 hours at 620 nm.

Example 3

Pyricularia Oryzae (Rice Blast)

(5) Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). After placing a DMSO solution of the test compositions into a microtiter plate (96-well format) the nutrient broth containing the fungal spores was added. The test plates were incubated at 24° C. and the inhibition of growth was determined photometrically after 72 hours.

Example 4

Venturia Inaequalis (Apple Scab)

(6) Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). After placing a DMSO solution of the test compositions into a microtiter plate (96-well format) the nutrient broth containing the fungal spores was added. The test plates were incubated at 24° C. and the inhibition of growth was determined photometrically after 7 days at 620 nm.

Example 5

Septoria Tritici (Leaf Blotch)

(7) Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). After placing a DMSO solution of the test compositions into a microtiter plate (96-well format) the nutrient broth containing the fungal spores was added. The test plates were incubated at 24° C. and the inhibition of growth was determined photometrically after 72 hours.

Example 6

Mycosphaerella arachidis, Syn. Cercospora Arachidicola (Peanut Brown Leaf Spot)

(8) Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). After placing a DMSO solution of the test compositions into a microtiter plate (96-well format), the nutrient broth containing the fungal spores was added. The test plates were incubated at 24° C. and the inhibition of growth was determined photometrically after approximately 5-6 days.

Example 7

Pyrenophora Teres

(9) Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). After placing a DMSO solution of the test compositions into a microtiter plate (96-well format) the nutrient broth containing the fungal spores was added. The test plates were incubated at 24° C. and the inhibition of growth was determined photometrically after 72 hours.

Example 8

Ramularia Collo-Cygni

(10) Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). After placing a DMSO solution of the test compositions into a microtiter plate (96-well format) the nutrient broth containing the fungal spores was added. The test plates were incubated at 24° C. and the inhibition of growth was determined photometrically after approximately 4 days.

(11) Results:

(12) Results from the tests outlined above are shown below in Tables 1 to 4. These data show that synergistic fungicidal activity is observed for the combination of florylpicoxamid and another active ingredient of component (B) against Pyricularia oryzae and Mycosphaerella arachidis at certain weight ratios.

(13) TABLE-US-00001 TABLE 1 Fungicidal activity of a composition of florylpicoxamid and benzovindiflupyr against Pyricularia oryzae as described in Example 3 above. Expected (additive) Combined florylpicoxamid benzovindiflupyr Ratio florylpicoxamid benzovindiflupyr actvity inhibition (A) (B) compound (A) (B) (Colby) (observed) (ppm) (ppm) (A):(B) inhibition (%) inhibition (%) (%) (%) 0.0031 0 0.0063 0 0.0125 0 0.0250 0 0.0500 0 0.1000 20 0.0125 20 0.0250 50 0.0500 70 0.1000 90 0.0031 0.0125 1:4 20 50 0.0063 0.0250 1:4 50 70 0.0125 0.0250 1:2 50 70 0.0125 0.0500 1:4 70 90 0.0250 0.0500 1:2 70 90 0.0250 0.1000 1:4 90 100 0.0500 0.0250 2:1 50 70 0.0500 0.1000 1:2 90 100 0.1000 0.0250 4:1 60 90 0.1000 0.0500 2:1 76 90

(14) TABLE-US-00002 TABLE 2 Fungicidal activity of a composition of florylpicoxamid and azoxystrobin against Pyricularia oryzae as described in Example 3 above. Expected (additive) Combined florylpicoxamid azoxystrobin Ratio florylpicoxamid azoxystrobin actvity inhibition (A) (B) compound (A) (B) (Colby) (observed) (ppm) (ppm) (A):(B) inhibition (%) inhibition (%) (%) (%) 0.1000 20 0.2000 50 0.0250 0 0.0500 0 0.1000 0 0.2000 0 0.1000 0.0250 4:1 20 50 0.1000 0.0500 2:1 20 50 0.1000 0.1000 1:1 20 50 0.1000 0.2000 1:2 20 90 0.2000 0.0500 4:1 50 70 0.2000 0.1000 2:1 50 70 0.2000 0.2000 1:1 50 70

(15) TABLE-US-00003 TABLE 3 Fungicidal activity of a composition of florylpicoxamid and chlorothaolnil against Pyricularia oryzae as described in Example 3 above. Expected (additive) Combined florylpicoxamid chlorothalonil Ratio florylpicoxamid chlorothalonil actvity inhibition (A) (B) compound (A) (B) (Colby) (observed) (ppm) (ppm) (A):(B) inhibition (%) inhibition (%) (%) (%) 0.0250 0 0.0500 20 0.1000 30 0.2000 60 0.2500 0 0.5000 0 1.0000 20 0.0250 1.0000 1:4 20 50 0.0500 0.2500 2:1 20 50 0.0500 1.0000 1:2 36 100 0.1000 0.2500 4:1 30 60 0.1000 0.5000 2:1 30 70 0.1000 1.0000 1:1 44 100 0.2000 0.5000 4:1 60 90 0.2000 1.0000 2:1 68 100

(16) TABLE-US-00004 TABLE 4 Fungicidal activity of a composition of florylpicoxamid and pydiflumetofen against Mycosphaerella arachidis as described in Example 6 above. Expected Combined florylpicoxamid pydiflumetofen Ratio florylpicoxamid pydiflumetofen (additive) inhibition (A) (B) compound (A) (B) actvity (observed) (ppm) (ppm) (A):(B) inhibition (%) inhibition (%) (Colby) (%) (%) 0.0250 4 0.0500 15 0.1000 38 0.0025 1 0.0050 0 0.0100 28 0.0200 70 0.0250 0.0050 1:2 4 63 0.0250 0.0100 1:4 31 98 0.0500 0.0050 1:1 15 58 0.0500 0.0100 1:2 39 95 0.0500 0.0200 1:4 74 100 0.1000 0.0025 4:1 38 85 0.1000 0.0050 2:1 38 75 0.1000 0.0100 1:1 55 95 0.1000 0.0200 1:2 81 99