CA2192493C - Fungicidal mixtures - Google Patents
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- CA2192493C CA2192493C CA002192493A CA2192493A CA2192493C CA 2192493 C CA2192493 C CA 2192493C CA 002192493 A CA002192493 A CA 002192493A CA 2192493 A CA2192493 A CA 2192493A CA 2192493 C CA2192493 C CA 2192493C
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- dithiocarbamate
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- ethylenebis
- zinc
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/50—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids the nitrogen atom being doubly bound to the carbon skeleton
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- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Described are fungicidal mixtures containing: a) the oxime ether carboxylic acid ester of formula (1) and (h) a dithiocarbamate (II) selected from the group: manganese ethylene-bis(dithiocarbamate)(zinc complex) (IIa); manganese ethylene-bis (dithiocarbamate)(IIb); zinc ammoniate ethylene-bis(dithiocarbamate) (llc) and zinc ethylene-bis-(dithiocarbamate)(IId) in a synergistically effective amount.
Description
=
Fungicidal mixtures The present invention relates to a fungicidal mixture which com-prises a) the oxime ether carboxylic ester of the formula Ia or Ib ~ I CH3 Q C'~4 C=NOCH3 C=NOCH3 Io2CH3 CH3 C02CH3 Ia Ib and b) a dithiocarbamate (II) selected from the group consisting of - manganese ethylenebis(dithiocarbamate) (zinc complex) (IIa), - manganese ethylenebis(dithiocarbamate) (IIb), - zinc ammoniate ethylenebis(dithiocarbamate) (Iic) and - zinc ethylenebis(dithiocarbamate) (IId) in a synergistically effective amount.
The present invention also relates to methods for controlling harmful fungi using mixtures of compounds I and II and to the use of compounds I and compounds II for producing mixtures of this type.
The compounds of the formula I (or Ia and Ib), their preparation and their action against harmful fungi is disclosed in the liter-ature (EP-A 253 213).
Likewise known are the dithiocarbamates II (IIa: common name:
mancozeb, US-A 3,379,610; IIb: common name: maneb, US-A
Fungicidal mixtures The present invention relates to a fungicidal mixture which com-prises a) the oxime ether carboxylic ester of the formula Ia or Ib ~ I CH3 Q C'~4 C=NOCH3 C=NOCH3 Io2CH3 CH3 C02CH3 Ia Ib and b) a dithiocarbamate (II) selected from the group consisting of - manganese ethylenebis(dithiocarbamate) (zinc complex) (IIa), - manganese ethylenebis(dithiocarbamate) (IIb), - zinc ammoniate ethylenebis(dithiocarbamate) (Iic) and - zinc ethylenebis(dithiocarbamate) (IId) in a synergistically effective amount.
The present invention also relates to methods for controlling harmful fungi using mixtures of compounds I and II and to the use of compounds I and compounds II for producing mixtures of this type.
The compounds of the formula I (or Ia and Ib), their preparation and their action against harmful fungi is disclosed in the liter-ature (EP-A 253 213).
Likewise known are the dithiocarbamates II (IIa: common name:
mancozeb, US-A 3,379,610; IIb: common name: maneb, US-A
2,504,404; IIc: former common name: metiram, US-A 3,248,400; IId:
common name: zineb, US-A 2,457,674), their preparation and their action against harmful fungi. -It is an object of the present invention, with a view to reducing the application rates and improving the spectrum of action of the known compounds, to provide mixtures which have an improved effect ori harmful fungi while the total amount of active ingredi-ents applied is reduced (synergistic mixtures).
We have found that this object is achieved by the mixtures de-fined at the outset. We have also found that harmful fungi can be controlled better on simultaneous conjoint or separate use of the compounds I and compounds II or on use of the compounds I and compounds II successively than with the individual compounds.
The compounds of the formula I can have the E or Z configuration for the C=X double bond (relative to the carboxyl group). Accord-ingly, they can each be used either as pure E or Z isomer or as E/Z isomer mixture in the mixture according to the invention. The E/Z isomer mixture or the E isomer is preferably used, and the E
isomer is particularly preferred.
The pure active ingredients I and II are prefe.rably employed in the preparation of the mixtures, which can as required be admixed with further active ingredients against harmful fungi or other pests such as insects, arachnids or nematodes, or else herbicidal or growth-regulating active ingredients or fertilizers.
The mixtures of compounds I and II and simultaneous conjoint or separate use of the compounds I and II are distinguished by an excellent action against a wide range of phytopathogenic fungi, in particular from the class of Ascomycetes and Basidiomycetes.
Some of them have systemic activity and can therefore also be used as foliar and soil fungicides.
They are particularly important for controlling a large number of fungi on a variety of crop plants such as cotton, vegetables (eg.
cucumbers, beans and cucurbits), barley, grass, oats, coffee, corn, fruit plants, rice, rye, soybean, grapevines, wheat, orna-mental plants, sugar cane and a large number of seeds.
They are particularly suitable for controlling the following phy-topathogenic fungi: Erysiphe graminis (powdery mildew) on cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea on curcurbits, Podosphaera leucotricha on apples, Uncinula necator on vines, Puccinia species on cereals, Rhizoctonia species on cotton and lawns, Ustilago species on cereals and sugar cane, Venturia inaequalis (scab) on apples, H-lminthosporium species on cereals, Septoria nodorum on wheat, Botrytis cinera (gray mold) on strawberries and vines, Cercospora arachidicola on peanuts, Pseudocercosporella herpotrichoides on wheat and barley, Pyricularia oryzae on rice, Phytophthora infestans on potatoes 2 ? 92493 and tomatoes, Plasmopara viticola on vinesr Alternaria species on vegetables and fruit and Fusarium and Verticillium species.
They can also be used in material protection (eg. wood protec-tion), for example against Paecilomyces variotii.
The compounds I and II can be applied simultaneously, conjointly or separately, or successively, and the sequence of separate ap-plication generally has no effect on the result of control.
The compounds I and II are normally used in a ratio by weight of from 50:1 to 2:1, preferably 40:1 to 1.8:1, in particular 30:1 to 1.8:1 (11:1).
The application rates of the mixtures according to the invention depend on the nature of the desired effect and are from 0.005 to 0.5 kg/ha, preferably 0.01 to 0.5 kg/ha, in particular 0.01 to 0.3 kg/ha, for compounds I. The application rates for compounds II are correspondingly from 0.1 to 10 kg/ha, preferably 0.5 to 5 kg/ha, in particular 1 to 4 kg/ha.
The application rates of the mixture for seed treatment are gen-erally from 0.001 to 100 g/kg of seeds, preferably 0.01 to 50 g/
kg, in particular 0.01 to 10 g/kg.
Where harmful fungi which are pathogenic for plants are to be controlled, the separate or conjoint application of the compounds I and II or of the mixtures of compounds I and II takes place by spraying or dusting the seeds, the plants or the soil before or after sowing the plants or before or after emergence of the plants.
The fungicidal synergistic mixtures according to the invention, or the compounds I and II can be prepared, for example, in the form of directly sprayable solutions, powders and suspensions or in the form of high-percentage aqueous, oily or other suspen-sions, dispersions, emulsions, oil dispersions, pastes, dusting agents, scatteriug agents or granules, and be used by spraying, atomizing, dusting, scattering or pouring. The application form depends on the purpose of use; it should in every case ensure dispersion of the mixture according to the invention which is as fine and uniform as possible.
The formulations are produced in a conventional way, eg. by ad-ding solvents and/or carriers. Inert additives such as emulsifi-ers or dispersants are normally mixed with the formulations.
Suitable surface-active substances are the-alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic acids, eg.
lignin-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl- and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols or fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or of naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenol or tributylphenyl polyglycol ether, alkylaryl polyether alkohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignin sulfite waste liquors or methylcellulose.
Scattering and dusting powders can be produced by mixing or mill-ing together the compounds I or II or the mixture of compounds I
and II with a solid carrier.
Granules (eg. coated, impregnated or homogenous granules) are normally produced by binding the active ingredient or ingredients on a solid carrier.
Examples of fillers and solid carriers which are used are mineral earths such as silica gel, silicas, silica gels,silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolo-mite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground plastics, and fertilizers such as ammo-nium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, bark meal, wood meal and nutshell meal, cellulose powder or other solid carriers.
The formulations generally contain from 0.1 to 95 % by weight, preferably 0.5 to 90 % by weight, of one of the compounds I or II
or the mixture of compounds I and II. The active ingredients are employed for this.purpose in a purity of from 90 % to 100 %, pre-ferably 95 % to 100 $(according to NMR or HPLC spectrum).
The compounds I or II or the mixtures or the corresponding for-mulations are used for treating the harmful fungi, or the plants, seeds, soil, areas, materials or rooms which are to be kept free of them with a fungicidally effective amount of the mixture or of the compounds I and II on separate application. The use can take place before or after attack by the harmful fungi.
~ 21924 93 Examples of the synergistic effect of the mixtures according to the invention against harmful fungi.
The fungicidal action of the compounds and of the mixtures was shown by the following test:
The active ingredients were prepared separately or conjointly as 20 % strength emulsion in a mixture of 70 % by weight of cyclo-hexanone, 20 % by weight of NekanilLN LN (Lutensol(D AP6, wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) and 10 B by weight of Emulphor EL (Emulan(t EL, emulsifier based on ethoxylated fatty alcohols) and diluted to the required concentration with water.
Evaluation took place by establishing the percentage of leaf area attacked. These percentages were converted into efficacies. The efficacies to be expected for the active ingredient mixtures were determined by the Colby formula.[R.S. Colby, Weeds 15, 20-22 (1967)] and compared with the observed efficacies.
Colby formula:
E=x+y-x=y/100 E efficacy to be expected, expressed as ~ of untreated control on use of the mixture of active ingredients A and B in con-centrations a and b x the efficacy expressed as % of the untreated control on use of active ingredient A in concentration a y the efficacy expressed as t of the untreated control on use of active ingredient B in concentration b An efficacy of 0 means that the attack on the treated plants cor-responds to that on the untreated control plants; an efficacy of 100 means that the treated plants show no attack.
A. Efficacy against Plasmopara viticola (vine peronospora) Pot vines (variety: MUller Thurgau) were sprayed to run-off with the active ingredient preparation. After 8 days, the plants were sprayed with a suspension of zoospores of the fungus Plasmopara viticola and initially stored at 24*C and 100 8 humidity for 48 h.
The test plants were then left in a glasshouse at 20-30*C for 5 days. Before the assessment, the plants were stored at high humidity'for a further 16 h. The evaluation took place by inspec-tion of the undersides of the leaves.
Active ingredient Application rate Efficacy [~]
[ppm]
-/-' - 0 Ia 31 48 Ia 8 0 IIc 310 80 IIc 80 48 Mixture Efficacy Efficacy [application [observed] [calculated]
rate]
Ia + IIc 100 90 31 + 310 Ia + IIc 95 48 8 + 80 * 77% attack of untreated control B: Efficacy against Phytophthora infestans (late blight) Leaves of tomato plants (variety: GroBe Fleischtomate) were initially treated with the aqueous preparation of the active ingredients. After about 48 h, the plants were infected with a suspension of zoospores of Phytophthora infestans. The plants treated in this way were then incubated at 16-180C and a relative humidity of 100 % for 6 days. The extent of fungal development was then determined.
=' 0050/44938 ~ 2 l 92 493 Active ingredient Application rate Efficacy [R]
[ppm]
-/-' - 0 Ia 8 70 Ia 4 40 Ilc 80 85 Ilc 40 79 Mixture 8fficacy Efficacy [application [observed] [calculated]
rate]
Ia + Ilc 100 95 8 + 80 Ia + Ilc 94 88 4 + 40 * 34% attack of untreated control
common name: zineb, US-A 2,457,674), their preparation and their action against harmful fungi. -It is an object of the present invention, with a view to reducing the application rates and improving the spectrum of action of the known compounds, to provide mixtures which have an improved effect ori harmful fungi while the total amount of active ingredi-ents applied is reduced (synergistic mixtures).
We have found that this object is achieved by the mixtures de-fined at the outset. We have also found that harmful fungi can be controlled better on simultaneous conjoint or separate use of the compounds I and compounds II or on use of the compounds I and compounds II successively than with the individual compounds.
The compounds of the formula I can have the E or Z configuration for the C=X double bond (relative to the carboxyl group). Accord-ingly, they can each be used either as pure E or Z isomer or as E/Z isomer mixture in the mixture according to the invention. The E/Z isomer mixture or the E isomer is preferably used, and the E
isomer is particularly preferred.
The pure active ingredients I and II are prefe.rably employed in the preparation of the mixtures, which can as required be admixed with further active ingredients against harmful fungi or other pests such as insects, arachnids or nematodes, or else herbicidal or growth-regulating active ingredients or fertilizers.
The mixtures of compounds I and II and simultaneous conjoint or separate use of the compounds I and II are distinguished by an excellent action against a wide range of phytopathogenic fungi, in particular from the class of Ascomycetes and Basidiomycetes.
Some of them have systemic activity and can therefore also be used as foliar and soil fungicides.
They are particularly important for controlling a large number of fungi on a variety of crop plants such as cotton, vegetables (eg.
cucumbers, beans and cucurbits), barley, grass, oats, coffee, corn, fruit plants, rice, rye, soybean, grapevines, wheat, orna-mental plants, sugar cane and a large number of seeds.
They are particularly suitable for controlling the following phy-topathogenic fungi: Erysiphe graminis (powdery mildew) on cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea on curcurbits, Podosphaera leucotricha on apples, Uncinula necator on vines, Puccinia species on cereals, Rhizoctonia species on cotton and lawns, Ustilago species on cereals and sugar cane, Venturia inaequalis (scab) on apples, H-lminthosporium species on cereals, Septoria nodorum on wheat, Botrytis cinera (gray mold) on strawberries and vines, Cercospora arachidicola on peanuts, Pseudocercosporella herpotrichoides on wheat and barley, Pyricularia oryzae on rice, Phytophthora infestans on potatoes 2 ? 92493 and tomatoes, Plasmopara viticola on vinesr Alternaria species on vegetables and fruit and Fusarium and Verticillium species.
They can also be used in material protection (eg. wood protec-tion), for example against Paecilomyces variotii.
The compounds I and II can be applied simultaneously, conjointly or separately, or successively, and the sequence of separate ap-plication generally has no effect on the result of control.
The compounds I and II are normally used in a ratio by weight of from 50:1 to 2:1, preferably 40:1 to 1.8:1, in particular 30:1 to 1.8:1 (11:1).
The application rates of the mixtures according to the invention depend on the nature of the desired effect and are from 0.005 to 0.5 kg/ha, preferably 0.01 to 0.5 kg/ha, in particular 0.01 to 0.3 kg/ha, for compounds I. The application rates for compounds II are correspondingly from 0.1 to 10 kg/ha, preferably 0.5 to 5 kg/ha, in particular 1 to 4 kg/ha.
The application rates of the mixture for seed treatment are gen-erally from 0.001 to 100 g/kg of seeds, preferably 0.01 to 50 g/
kg, in particular 0.01 to 10 g/kg.
Where harmful fungi which are pathogenic for plants are to be controlled, the separate or conjoint application of the compounds I and II or of the mixtures of compounds I and II takes place by spraying or dusting the seeds, the plants or the soil before or after sowing the plants or before or after emergence of the plants.
The fungicidal synergistic mixtures according to the invention, or the compounds I and II can be prepared, for example, in the form of directly sprayable solutions, powders and suspensions or in the form of high-percentage aqueous, oily or other suspen-sions, dispersions, emulsions, oil dispersions, pastes, dusting agents, scatteriug agents or granules, and be used by spraying, atomizing, dusting, scattering or pouring. The application form depends on the purpose of use; it should in every case ensure dispersion of the mixture according to the invention which is as fine and uniform as possible.
The formulations are produced in a conventional way, eg. by ad-ding solvents and/or carriers. Inert additives such as emulsifi-ers or dispersants are normally mixed with the formulations.
Suitable surface-active substances are the-alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic acids, eg.
lignin-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl- and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols or fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or of naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenol or tributylphenyl polyglycol ether, alkylaryl polyether alkohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignin sulfite waste liquors or methylcellulose.
Scattering and dusting powders can be produced by mixing or mill-ing together the compounds I or II or the mixture of compounds I
and II with a solid carrier.
Granules (eg. coated, impregnated or homogenous granules) are normally produced by binding the active ingredient or ingredients on a solid carrier.
Examples of fillers and solid carriers which are used are mineral earths such as silica gel, silicas, silica gels,silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolo-mite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground plastics, and fertilizers such as ammo-nium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, bark meal, wood meal and nutshell meal, cellulose powder or other solid carriers.
The formulations generally contain from 0.1 to 95 % by weight, preferably 0.5 to 90 % by weight, of one of the compounds I or II
or the mixture of compounds I and II. The active ingredients are employed for this.purpose in a purity of from 90 % to 100 %, pre-ferably 95 % to 100 $(according to NMR or HPLC spectrum).
The compounds I or II or the mixtures or the corresponding for-mulations are used for treating the harmful fungi, or the plants, seeds, soil, areas, materials or rooms which are to be kept free of them with a fungicidally effective amount of the mixture or of the compounds I and II on separate application. The use can take place before or after attack by the harmful fungi.
~ 21924 93 Examples of the synergistic effect of the mixtures according to the invention against harmful fungi.
The fungicidal action of the compounds and of the mixtures was shown by the following test:
The active ingredients were prepared separately or conjointly as 20 % strength emulsion in a mixture of 70 % by weight of cyclo-hexanone, 20 % by weight of NekanilLN LN (Lutensol(D AP6, wetting agent with emulsifying and dispersing action based on ethoxylated alkylphenols) and 10 B by weight of Emulphor EL (Emulan(t EL, emulsifier based on ethoxylated fatty alcohols) and diluted to the required concentration with water.
Evaluation took place by establishing the percentage of leaf area attacked. These percentages were converted into efficacies. The efficacies to be expected for the active ingredient mixtures were determined by the Colby formula.[R.S. Colby, Weeds 15, 20-22 (1967)] and compared with the observed efficacies.
Colby formula:
E=x+y-x=y/100 E efficacy to be expected, expressed as ~ of untreated control on use of the mixture of active ingredients A and B in con-centrations a and b x the efficacy expressed as % of the untreated control on use of active ingredient A in concentration a y the efficacy expressed as t of the untreated control on use of active ingredient B in concentration b An efficacy of 0 means that the attack on the treated plants cor-responds to that on the untreated control plants; an efficacy of 100 means that the treated plants show no attack.
A. Efficacy against Plasmopara viticola (vine peronospora) Pot vines (variety: MUller Thurgau) were sprayed to run-off with the active ingredient preparation. After 8 days, the plants were sprayed with a suspension of zoospores of the fungus Plasmopara viticola and initially stored at 24*C and 100 8 humidity for 48 h.
The test plants were then left in a glasshouse at 20-30*C for 5 days. Before the assessment, the plants were stored at high humidity'for a further 16 h. The evaluation took place by inspec-tion of the undersides of the leaves.
Active ingredient Application rate Efficacy [~]
[ppm]
-/-' - 0 Ia 31 48 Ia 8 0 IIc 310 80 IIc 80 48 Mixture Efficacy Efficacy [application [observed] [calculated]
rate]
Ia + IIc 100 90 31 + 310 Ia + IIc 95 48 8 + 80 * 77% attack of untreated control B: Efficacy against Phytophthora infestans (late blight) Leaves of tomato plants (variety: GroBe Fleischtomate) were initially treated with the aqueous preparation of the active ingredients. After about 48 h, the plants were infected with a suspension of zoospores of Phytophthora infestans. The plants treated in this way were then incubated at 16-180C and a relative humidity of 100 % for 6 days. The extent of fungal development was then determined.
=' 0050/44938 ~ 2 l 92 493 Active ingredient Application rate Efficacy [R]
[ppm]
-/-' - 0 Ia 8 70 Ia 4 40 Ilc 80 85 Ilc 40 79 Mixture 8fficacy Efficacy [application [observed] [calculated]
rate]
Ia + Ilc 100 95 8 + 80 Ia + Ilc 94 88 4 + 40 * 34% attack of untreated control
Claims (12)
1. A fungicidal mixture comprising a) the oxime ether carboxylic ester of the formula Ia or lb and b) a dithiocarbamate (II) selected from the group consisting of - manganese ethylenebis(dithiocarbamate) (zinc complex) (IIa), - manganese ethylenebis(dithiocarbamate) (IIb), - zinc ammoniate ethylenebis(dithiocarbamate) (IIc) and - zinc ethylenebis(dithiocarbamate) (IId) in a synergistically effective amount.
2. The fungicidal mixture as claimed in claim 1, comprising an oxime ether carboxamide of the formula Ia or Ib as set forth in claim 1 and manganese ethylenebis(dithiocarbamate) (zinc complex) (IIa).
3. The fungicidal mixture as claimed in claim 1, comprising an oxime ether carboxamide of the formula Ia or Ib as set forth in claim 1 and manganese ethylenebis(dithiocarbamate) (IIb).
4. The fungicidal mixture as claimed in claim 1, comprising an oxime ether carboxamide of the formula Ia or Ib as set forth in claim 1 and zinc ammoniate ethylenebis(dithiocarbamate) (IIc).
5. The fungicidal mixture as claimed in claim 1, comprising an oxime ether carboxamide of the formula Ia or Ib as set forth in claim 1 and zinc ethylenebis(dithiocarbamate) (IId).
6. The fungicidal mixture as claimed in claim 1, wherein the ratio by weight of compound II to compound I is from 50:1 to 2:1.
7. A method for controlling harmful fungi in their habitat or the plants, seeds, soil, areas, materials or rooms to be kept free of them, comprising treating a surface wherein the harmful fungi are located, with the compounds of formulae I
and II as defined in claim 1, the compounds I and II being used in synergistically effective amounts.
and II as defined in claim 1, the compounds I and II being used in synergistically effective amounts.
8. The method as claimed in claim 7, wherein the compound I and the compound II are applied simultaneously, conjointly or separately, or successively.
9. The method as claimed in claim 7, wherein the surface is treated with from 0.005 to 0.5 kg of the compound of formula I per hectare of the surface.
10. The method as claimed in claim 7, wherein the surface is treated with from 0.1 to 10 kg of the compound of formula II per hectare of the surface.
11. Use of the compound I as set forth in claim 1 for producing a fungicidally effective synergistic mixture as claimed in claim 1.
12. Use of the compound II as set forth in claim 1 for producing a fungicidally effective synergistic mixture as claimed in claim 1.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4420277.6 | 1994-06-10 | ||
| DE4420277A DE4420277A1 (en) | 1994-06-10 | 1994-06-10 | Fungicidal mixtures |
| PCT/EP1995/001953 WO1995034205A1 (en) | 1994-06-10 | 1995-05-23 | Fungicidal mixtures |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2192493A1 CA2192493A1 (en) | 1995-12-21 |
| CA2192493C true CA2192493C (en) | 2007-07-24 |
Family
ID=38325178
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002192493A Expired - Fee Related CA2192493C (en) | 1994-06-10 | 1995-05-23 | Fungicidal mixtures |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2192493C (en) |
-
1995
- 1995-05-23 CA CA002192493A patent/CA2192493C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2192493A1 (en) | 1995-12-21 |
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| Date | Code | Title | Description |
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Effective date: 20150525 |