FUNGICIDAL COMPOSITIONS

Abstract

A composition suitable for control of diseases caused by phytopathogens comprising (A) a compound of formula (I), wherein R.sup.1 is either H, C(O)CH.sub.3 or C(O)CH.sub.2CH.sub.3; and (B) at least one compound selected from compounds known for their fungicidal activity; and a method of controlling diseases on useful plants, especially rust diseases on soybeans or cereals.

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Claims

1. A composition suitable for control of diseases caused by phytopathogens comprising (A) a compound of formula I: ##STR00007## wherein R.sup.1 is selected from H, C(O)CH.sub.3 or C(O)CH.sub.2CH.sub.3, or mixtures thereof, or an agrochemically acceptable salt or N-oxide thereof; and (B) at least one compound selected from the group consisting of 4-[6-[2-[2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, N-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine, N-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide, 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide and N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide or combinations thereof.

2. A fungicidal composition, comprising a fungicidally effective amount of a composition according to claim 1, and a suitable carrier or diluent therefore, and optionally, comprising further pesticides, such as preferably, fungicides, insecticides or herbicides.

3. A formulation comprising a composition according to claim 2, comprising from 0.01 to 90% by weight of active agent, from 0 to 20% agriculturally acceptable surfactant and of from 10 to 99.99% solid or liquid formulation inerts and adjuvant(s), wherein the active agent comprises of at least a compound of component (A), together with a compound of component (B), and optionally other active agents, particularly microbiocides or conservatives or the like.

4. A concentrated composition for dilution by the user, comprising a composition according to claim 1, comprising of from 2 to 80%, preferably between about 5 and 70% by weight of the active agent.

5. A seed dressing formulation, wherein the composition further comprises a diluent, preferably wherein the formulation is an aqueous suspension or in a dry powder form having good adherence to the plant propagation materials.

6. A seed dressing formulation according to claim 5, comprising the combination of active ingredients according to claim 5 in encapsulated form, as slow release capsules or microcapsules.

7. A method of combating and controlling phytopathogens, comprising applying a fungicidally effective amount of a composition according to claim 1, to a pest, a locus of pest, or to a plant susceptible to attack by a pest, with the exception of a method for treatment of the human or animal body by surgery or therapy and diagnostic methods practiced on the human or animal body.

8. The method according to claim 7, for controlling rust diseases on soybeans or on cereals which comprises applying to the plants.

9. The method according to claim 6, wherein the phytopathogen is Phakopsora pachyrhizi.

10. The method according to claim 7, wherein the composition further comprises a diluent, preferably as an aqueous suspension or in a dry powder form having good adherence to the plant propagation materials.

11. Plant propagation material treated in accordance with the method described in claim 10.

12. Use of a composition according to claim 1, for combating and controlling phytopathogens.

13. The use according to claim 12, for combating and controlling Phakopsora pachyrhizi in soybean plants.

Description

FORMULATION EXAMPLES

[0073]

TABLE-US-00001 Wettable powders a) b) active ingredient [A):B) = 1:3(a), 1:1(b)] 25% 75% sodium lignosulfonate 5% sodium lauryl sulfate 3% 5% sodium diisobutylnaphthalenesulfonate 10% (7-8 mol of ethylene oxide) highly dispersed silicic acid 5% 10% kaolin 62%

[0074] The active ingredient is thoroughly mixed with the other formulation components and the mixture is thoroughly ground in a suitable mill, affording wettable powders that can be diluted with water to give suspensions of the desired concentration.

TABLE-US-00002 Powders for dry seed treatment a) b) active ingredient [A):B) = 1:3(a), 1:1(b)] 25% 75% light mineral oil 5% 5% highly dispersed silicic acid 5% kaolin 65% talc 20

[0075] The active ingredient is thoroughly mixed with the other formulation components and the mixture is thoroughly ground in a suitable mill, affording powders that can be used directly for seed treatment.

TABLE-US-00003 Emulsifiable concentrate active ingredient (A):B) = 1:6) 10% octylphenol polyethylene glycol ether 3% (4-5 mol of ethylene oxide) calcium dodecylbenzenesulfonate 3% castor oil polyglycol ether (35 mol of ethylene oxide) 4% cyclohexanone 30% xylene mixture 50%

[0076] Emulsions of any required dilution, which can be used in plant protection, can be obtained from this concentrate by dilution with water.

TABLE-US-00004 Dustable powders a) b) active ingredient [A):B) = 1:6(a), 1:10(b)] 5% 6% talcum 95% kaolin 94%

[0077] Ready-for-use dusts are obtained by mixing the active ingredient with the carriers and grinding the mixture in a suitable mill. Such powders can also be used for dry dressings for seed.

TABLE-US-00005 Extruded granules % w/w active ingredient (A):B) = 2:1) 15% sodium lignosulfonate 2% sodium alkyl naphthalene sulfonate 1% kaolin 82%

[0078] The active ingredient is mixed and ground with the other formulation components, and the mixture is moistened with water. The mixture is extruded and then dried in a stream of air.

TABLE-US-00006 Suspension concentrate active ingredient (A):B) = 1:8) 40% propylene glycol 10% nonylphenol polyethylene glycol ether (15 mol of ethylene oxide) 6% sodium lignosulfonate 10% carboxymethylcellulose 1% silicone oil (in the form of a 75% emulsion in water) 1% water 32%

[0079] The finely ground active ingredient is intimately mixed with the other formulation components, giving a suspension concentrate which can be diluted in water at any desired rate. Using such dilutions, living plants as well as plant propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.

TABLE-US-00007 Flowable concentrate for seed treatment active ingredient (A):B) = 1:8) 40% propylene glycol 5% copolymer butanol PO/EO 2% tristyrenephenole ethoxylate (with 10-20 moles EO) 2% 1,2-benzisothiazolin-3-one 0.5%.sup. monoazo-pigment calcium salt 5% silicone oil (in the form of a 75% emulsion in water) 0.2%.sup. water 45.3%

[0080] The finely ground active ingredient is intimately mixed with the other formulation components, giving a suspension concentrate which can be diluted further in water to be applied to seeds. Using such dilutions, propagation material can be treated and protected against infestation by microorganisms, by spraying, pouring or immersion.

BIOLOGICAL EXAMPLES

[0081] Botrytis cinerea (Gray Mould):

[0082] Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). A DMSO solution of the test compounds was placed into a microtiter plate (96-well format) and the nutrient broth containing the fungal spores was added to it. The test plates were incubated at 24 C and the inhibition of growth was determined photometrically after 72 hrs.

TABLE-US-00008 N-methyl-4-[5- (trifluoromethyl)-1,2,4- COLBY Compound oxadiazol-3- Observed Expected A-1.2 yl]benzenecarbothioamide Activity Activity ppm ppm (%) (%) 2 70 20 70 6.66 20 2.22 0 2 20 100 70 2 6.66 100 20 2 2.22 90 0
Corynespora cassiicola (Target Leaf Spot):

[0083] Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). A DMSO solution of the test compounds was placed into a microtiter plate (96-well format) and the nutrient broth containing the fungal spores was added to it. The test plates were incubated at 24 C and the inhibition of growth was determined photometrically after 3-4 days at 620 nm.

TABLE-US-00009 4-[6-[2-(2,4-Difluorophenyl)- 1,1-difluoro-2-hydroxy-3- (5-thioxo-4H-1,2,4-triazol-1- COLBY Compound yl)propyl]-3- Observed Expected A-1.2 pyridyl]oxy]benzonitrile Activity Activity ppm ppm (%) (%) 0.06 0 2 20 1 0 0.5 0 0.06 2 50 20 0.06 1 50 0 0.06 0.5 20 0
Glomerella lagenarium syn. Colletotrichum lagenarium (Anthracnose):

[0084] Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). A DMSO solution of the test compounds was placed into a microtiter plate (96-well format) and the nutrient broth containing the fungal spores was added to it. The test plates were incubated at 24 C and the inhibition of growth was determined photometrically after 72 hrs at 620 nm.

TABLE-US-00010 2,2-Difluoro-N-methyl-2-[4- COLBY Compound [5-(trifluoromethyl)-1,2,4- Observed Expected A-1.2 oxadiazol-3-yl]phenyl]acetamide Activity Activity ppm ppm (%) (%) 0.1 0 0.02 0 0.08 20 0.1 0.08 50 20 0.02 0.08 50 20

TABLE-US-00011 N-methyl-4-[5-(trifluoromethyl)- COLBY Compound 1,2,4-oxadiazol-3- Observed Expected A-1.2 yl]benzenecarbothioamide Activity Activity ppm ppm (%) (%) 0.1 0 0.02 0 0.08 70 0.1 0.08 90 70 0.02 0.08 90 70

TABLE-US-00012 N-(2-fluorophenyl)-4-[5- COLBY Compound (trifluoromethyl)-1,2,4- Observed Expected A-1.2 oxadiazol-3-yl]benzamide Activity Activity ppm ppm (%) (%) 0.2 0 20 0 6.66 0 2.22 0 0.2 20 50 0 0.2 6.66 50 0 0.2 2.22 50 0
Phakopsora pachyrhizi (Soybean Rust):

[0085] Whole soybean plants are treated with the recited active ingredients 4 weeks after planting. 1 day after spraying leaf disks are cut from the first trifoliate leaf. Five repetitions at each rate are conducted. The leaf disks are inoculated with Phakopsora pachyrhizi (Asian soybean rust) one day after treatment. Evaluation of the leaf disks is conducted 11 to 14 days after inoculation and the activity is derived from the relation of the treated vs untreated, infested check. The rates of the active ingredients used are given in Table as g active ingredient (a.i.)/ha.

TABLE-US-00013 4-[[6-[2-(2,4-Difluorophenyl)- 1,1-difluoro-2-hydroxy-3-(5- thioxo-4H-1,2,4-triazol-1- COLBY Compound yl)propyl]-3- Observed Expected A-1.2 pyridyl]oxy]benzonitrile Activity Activity (g/ha) (g/ha) (%) (%) 0.6 55 0.3 18 60 10 30 0 0.6 60 85 60 0.6 30 87 55 0.3 60 48 26 0.3 30 37 18

TABLE-US-00014 N-(2-chloro-5-methyl-4- COLBY Compound phenoxy-phenyl)-N-ethyl- Observed Expected A-1.2 N-methyl-formamidine Activity Activity (g/ha) (g/ha) (%) (%) 0.6 55 0.3 18 3 71 1.5 71 0.6 3 91 87 0.6 1.5 87 87 0.3 3 88 77 0.3 1.5 84 77

TABLE-US-00015 N-[2-chloro-4-(2-fluorophenoxy)- COLBY Compound 5-methyl-phenyl]- Observed Expected A-1.2 N-ethyl-N-methyl-formamidine Activity Activity (g/ha) (g/ha) (%) (%) 0.6 55 0.3 18 3 80 1.5 46 0.6 3 90 91 0.6 1.5 81 76 0.3 3 87 83 0.3 1.5 61 55

TABLE-US-00016 2,2-Difluoro-N-methyl-2- [4-[5-(trifluoromethyl)- COLBY Compound 1,2,4-oxadiazol-3- Observed Expected A-1.2 yl]phenyl]acetamide Activity Activity (g/ha) (g/ha) (%) (%) 0.6 55 0.3 18 0.6 4 0.3 0 0.6 0.6 70 57 0.6 0.3 77 55 0.3 0.6 38 21 0.3 0.3 48 18

TABLE-US-00017 N-methyl-4-[5-(trifluoromethyl)- COLBY Compound 1,2,4-oxadiazol-3- Observed Expected A-1.2 yl]benzenecarbothioamide Activity Activity (g/ha) (g/ha) (%) (%) 0.6 55 0.3 18 0.6 74 0.3 6 0.6 0.3 81 58 0.3 0.3 65 23

TABLE-US-00018 N-(2-fluorophenyl)-4-[5- COLBY Compound (trifluoromethyl)-1,2,4- Observed Expected A-1.2 oxadiazol-3-yl]benzamide Activity Activity (g/ha) (g/ha) (%) (%) 0.6 55 0.3 18 0.6 35 0.3 0 0.6 0.6 81 71 0.6 0.3 58 55 0.3 0.6 75 47 0.3 0.3 60 18
Sclerotinia sclerotiorum (White Mold):

[0086] Mycelial fragments of the fungus prepared from a fresh liquid culture were directly mixed into nutrient broth (PDB potato dextrose broth). A DMSO solution of the test compounds was placed into a microtiter plate (96-well format) and the nutrient broth containing the fungal spores was added to it. The test plates were incubated at 24 C and the inhibition of growth was determined photometrically after 72 hrs at 620 nm

TABLE-US-00019 N-methyl-4-[5-(trifluoromethyl)- COLBY Compound 1,2,4-oxadiazol-3- Observed Expected A-1.2 yl]benzenecarbothioamide Activity Activity ppm ppm (%) (%) 2 70 0.2 0 0.1 0 0.02 0 20 20 2 20 90 76 0.2 20 50 20 0.1 20 50 20 0.02 20 50 20
Septoria glycines (Brown Spot):

[0087] Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). A DMSO solution of the test compounds was placed into a microtiter plate (96-well format) and the nutrient broth containing the fungal spores was added to it. The test plates were incubated at 24 C and the inhibition of growth was determined visually after 72 hrs.

TABLE-US-00020 4-[[6-[2-(2,4-Difluorophenyl)- 1,1-difluoro-2-hydroxy-3-(5- thioxo-4H-1,2,4-triazol-1- COLBY Compound yl)propyl]-3- Observed Expected A-1.2 pyridyl]oxy]benzonitrile Activity Activity ppm ppm (%) (%) 0.06 20 2 70 1 50 0.06 2 90 76 0.06 1 70 60

TABLE-US-00021 N-(2-chloro-5-methyl-4- COLBY Compound phenoxy-phenyl)-N-ethyl-N- Observed Expected A-1.2 methyl-formamidine Activity Activity ppm ppm (%) (%) 0.06 20 0.03 20 0.625 70 0.06 0.625 100 76 0.03 0.625 100 76
Septoria tritici (Leaf Blotch):

[0088] Conidia of the fungus from cryogenic storage were directly mixed into nutrient broth (PDB potato dextrose broth). A DMSO solution of the test compounds was placed into a microtiter plate (96-well format) and the nutrient broth containing the fungal spores was added to it. The test plates were incubated at 24 C and the inhibition of growth was determined photometrically after 72 hrs.

TABLE-US-00022 N-(2-chloro-5-methyl-4- COLBY Compound phenoxy-phenyl)-N-ethyl-N- Observed Expected A-1.2 methyl-formamidine Activity Activity ppm ppm (%) (%) 0.06 70 0.03 50 0.625 20 0.06 0.625 100 76 0.03 0.625 100 60

TABLE-US-00023 2,2-Difluoro-N-methyl-2-[4- COLBY Compound [5-(trifluoromethyl)-1,2,4- Observed Expected A-1.2 oxadiazol-3-yl]phenyl]acetamide Activity Activity ppm ppm (%) (%) 0.1 70 0.02 20 20 20 0.1 20 100 76 0.02 20 50 36

TABLE-US-00024 N-methyl-4-[5- (trifluoromethyl)-1,2,4- COLBY Compound oxadiazol-3- Observed Expected A-1.2 yl]benzenecarbothioamide Activity Activity ppm ppm (%) (%) 0.1 70 0.02 20 20 90 6.66 70 2.22 0 0.1 20 100 90 0.1 6.66 100 70 0.1 2.22 90 0 0.02 20 100 90 0.02 6.66 90 70 0.02 2.22 50 0 N-(2-fluorophenyl)-4-[5- COLBY Compound (trifluoromethyl)-1,2,4- Observed Expected A-1.2 oxadiazol-3-yl]benzamide Activity Activity ppm ppm (%) (%) 0.02 20 20 0 6.66 0 2.22 0 0.02 20 50 0 0.02 6.66 50 0 0.02 2.22 50 0