CA2139281A1 - Fungicidal mixtures - Google Patents

Fungicidal mixtures

Info

Publication number
CA2139281A1
CA2139281A1 CA002139281A CA2139281A CA2139281A1 CA 2139281 A1 CA2139281 A1 CA 2139281A1 CA 002139281 A CA002139281 A CA 002139281A CA 2139281 A CA2139281 A CA 2139281A CA 2139281 A1 CA2139281 A1 CA 2139281A1
Authority
CA
Canada
Prior art keywords
compound
formula
iii
acid
oxime ether
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
CA002139281A
Other languages
French (fr)
Inventor
Horst Wingert
Bernd Muller
Hubert Sauter
Eberhard Ammermann
Gisela Lorenz
Reinhold Saur
Klaus Schelberger
Manfred Hampel
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BASF SE filed Critical BASF SE
Priority to CA002139281A priority Critical patent/CA2139281A1/en
Publication of CA2139281A1 publication Critical patent/CA2139281A1/en
Abandoned legal-status Critical Current

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Classifications

    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • 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
    • A01N37/36—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 singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • 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
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof
    • 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
    • A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48

Landscapes

  • 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

A fungicidal mixture containing a) the oxime ether carboxamide of the formula I

and either b.1 the oxime ether carboxylic acid ester of the formula II

or b.2 the methoxyacrylic acid ester of the formula III

Description

~ BASF Aktiengesellschaft 931555 O.Z. 0050/44661 213~281 . .

Fungicidal mixtures The present invention relates to a fungicidal mixture which con-5 tains a) the oxime ether carboxamide of the formula I
10 ~o~/~

C=NOCH3 and either b.1 the oxime ether carboxylic acid ester of the formula II

~ ~

C=NOCH3 or b.2 the methoxyacrylic acid ester of the formula III

~N

CN C=CHOCH3 in a synergistically active amount.

40 The invention additionally relates to processes for controlling harmful fungi using mixtures of the compounds I and II or the compounds I and III and the use of the compound I, the com-pound II and the compound III for the production of mixtures of this type.

BASF Aktiengesellschaft 931555 O.Z. 0050/44661 213g281 The compound of the formula I, its preparation and its action against harmful fungi are disclosed in the literature (EP-A 477 631). The compound II (EP-A 253 213) and the com-pound III (EP-A 382 375), their preparation and their action 5 against harmful fungi are likewise known.

With respect to a decrease in the application rates and an im-provement of the spectrum of action of the known compounds, the present invention is based on mixtures which, with a reduced to-10 tal amount of applied active compounds, have an improved actionagainst harmful fungi (synergistic mixtures).

Accordingly, the mixtures defined at the beginning have been found. It has additionally been found that on simultaneous joint 15 or separate application of the compound I and the compound II or the compound I and the compound III or on application of the com-pound I and the compound II or the compound III succession harm-ful fungi can be controlled better than with the individual com-pounds.
The compounds of the formula I, II or III can be present in the E
or the Z configuration with respect to the C=X double bond (with respect to the carboxylic acid functional group). Accordingly, they can be used in the mixture according to the invention in 25 each case either as the pure E or Z isomer or as an E/Z isomer mixture. The E/Z isomer mixture or the E isomer is preferably used, the E isomer being particularly preferred.

Because of the basic character of the NH group, the compound I is 30 able to form salts or adducts with inorganic or organic acids or with metal ions.

Examples of inorganic acids are hydrohalic acids such as hydro-fluoric acid, hydrochloric acid, hydrobromic acid and hydriodic 35 acid, sulfuric acid, phosphoric acid and nitric acid.

Suitable organic acids are, for example, formic acid, carbonic acid and alkanoic acids such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid and also glycolic 40 acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, alkylsulfonic acids (sulfonic acids having straight-chain or branched alkyl radicals having l to 20 carbon atoms), arylsulfonic acids or -disulfonic acids (aromatic radicals such as phenyl and naphthyl which carry 45 one or two sulfonic acid groups), alkylphosphonic acids (phos-phonic acids containing straight-chain or branched alkyl radicals having 1 to 20 carbon atoms), arylphosphonic acids or BASF Aktiengesellschaft ~13 ~ ~5~5 Z. 0050/44661 diphosphonic acids (aromatic radicals such as phenyl and naphthyl which carry one or two phosphoric acid radicals)~ the alkyl and aryl radicals being able to carry further substituents, eg. p-to-luenesulfonic acid, salicylic acid, p-aminosalicylic acid, 2-phe-5 noxybenzoic acid, 2-acetoxybenzoic acid, dodecylbenzenesulfonic acid etc.

Suitable metal ions are in particular the ions of the elements of the second main group, in particular calcium and magnesium, of 10 the third and fourth main group, in particular aluminum, tin and lead, as well as of the first to eighth sub-group, in particular chromium, manganese, iron, cobalt, nickel, copper, zinc and oth-ers. The metal ions of the elements of the sub-groups of the fourth period are particularly preferred. The metals can in this 15 case be present in the different valencies applicable to them.

Preferably, the pure active compounds I and II or III are employed in the preparation of the mixtures, to which, if re-quired, further active compounds against harmful fungi or other 20 pests such as insects, arachnids or nematodes, or alternatively herbicidal or growth-regulating active compounds or fertilizers, can be admixed.

The mixtures of the compounds I and II or I and III and the si-25 multaneous joint or separate use of the compounds I and II or I
and III are distinguished by an outstanding action against a wide spectrum of phytopathogenic fungi, in particular from the Ascomy-cetes and Basidiomycetes class. In some cases they are systemi-cally active and can therefore also be employed as foliar and 30 soil fungicides.

They have particular importance for the control of a multiplicity of fungi on various crop plants such as cotton, vegetable plants (eg. cucumbers, beans and cucurbits), barley, grass, oats, cof-35 fee, maize, fruit plants, rice, rye, soybean, grape, wheat, deco-rative plants, sugar cane and a multiplicity of seeds.

In particular, they are suitable for the control of the following phytopathogenic fungi: Erysiphe graminis (powdery mildew) on ce-40 reals, Erysiphe cichoracearum and Sphaerotheca fuliginea on cu-curbits, Podosphaera leucotricha on apples, Puccinia species on cereals, Rhizoctonia species on cotton and lawns, Ustilago spe-cies on cereals and sugar cane, Venturia inaequalis (scab) on ap-ples, Helminthosporium species on cereals, Septoria nodorum on 45 wheat, Botrytis cinerea (gray mold) on strawberries and vines, Cercospora arachidicola on groundnuts, Pseudocercosporella herpo-trichoides on wheat and barley, Pyricularia oryzae on rice, BASF Aktiengesellschaft 931555 O.Z. 0050/44661 Phytophthora infestans on potatoes and tomatoes, Plasmopara viti-cola on vines, Alternaria species on vegetables and fruit and also Fusarium and Verticillium species.

5 They are additionally applicable in the protection of materials (eg. wood preservation), for example against Paecilomyces variotii.

The compounds I and II or I and III can be applied simultaneously 10 jointly or separately, or succession, the sequence in the case of separate application in general having no effect on the control success.

The compounds I and II or I and III are customarily applied in a lS weight ratio of from 10:1 to 0.1:1, preferably from 5:1 to 0.2:1, in particular from 3:1 to 0.3:1.

Depending on the type of effect desired, the application rates in the mixtures according to the invention are from 0.02 to 1 kg/ha, 20 preferably from 0.05 to 1 kg/ha, in particular from 0.1 to 0.8 kg/ha. The application rates here for the compound I are from 0.005 to 0.5 kg/ha, preferably from 0.005 to 0.3 kg/ha, in par-ticular from 0.005 to 0.3 kg/ha. The application rates for the compound II or the compound III are correspondingly from 0.01 to 25 0.5 kg/ha, preferably from 0.01 to 0.5 kg/ha, in particular from 0.01 to 0.3 kg/ha.

In the treatment of seed, application rates of mixture of from 0.001 to 50 g/kg of seed, preferably from 0.01 to 10 g/kg, in 30 particular from 0.01 to 5 g/kg, are in general used.

If harmful fungi which are pathogenic for plants are to be con-trolled, the separate or joint application of the compounds I
and II or I and III or of the mixtures of the compounds I and II
35 or I and III is carried out by spraying or dusting the seeds, the plants or the soil before or after sowing of the plants or before or after emergence of the plants.

The fungicidal synergistic mixtures and the compounds I and II or 40 I and III according to the invention can be prepared, for exam-ple, in the form of directly sprayable solutions, powders and suspensions or in the form of high-percentage aqueous, oily or other suspensions, dispersions, emulsions, oil dispersions, pastes, dusting compositions, broadcasting compositions or gran-45 ules and applied by spraying, atomizing, dusting, broadcasting orwatering. The application form is dependent on the intended use;
it should in each case guarantee a dispersion of the mixture BASF Aktiengesellschaft 931555 O.Z. 0050/44661 213g~8:1 _ 5 according to the invention which is as fine and uniform as pos-sible.

The formulations are prepared in a manner known per se, eg. by 5 addition of solvents and/or carriers. Inert additives such as emulsifiers or dispersants are customarily admixed to the formulations.

Suitable surface-active substances are the alkali metal, alkaline 10 earth metal or ammonium salts of aromatic sulfonic acids, eg.
lignosulfonic acid, phenolsulfonic acid, naphthalenesulfonic acid and dibutylnaphthalenesulfonic acid, as well as of fatty acids, alkyl- and alkylarylsulfonates, alkyl-, lauryl ether and fatty alcohol sulfates, and also salts of sulfated hexa-, hepta- and 15 octadecanols or fatty alcohol glycol ethers, condensation prod-ucts of sulfonated naphthalene and its derivatives with formalde-hyde, condensation products of naphthalene or of naphthalenesul-fonic acids with phenol and formaldehyde, polyoxyethylene octyl-phenol ethers, ethoxylated isooctyl-, octyl- or nonylphenol, al-20 kylphenol or tributylphenyl polyglycol ethers, alkylaryl poly-ether alcohols, isotridecyl alcohol, fatty alcohol-ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene or polyoxy-propylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignin-sulfite waste liquors or methylcellulose.
Powder, broadcasting and dusting compositions can be prepared by mixing or joint grinding of the compounds I or II or I or III or the mixture of the compounds I and II or I and III with a solid carrier.
Granules (eg. coated, impregnated or homogeneous granules) are customarily prepared by binding the active compound or the active compounds to a solid carrier.

35 Fillers or solid carriers used are, for example, mineral earths such as silica gel, silicic acids, silicates, talc, kaolin, lime-stone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, and fertilizers such as ammonium sulfate, ammonium 40 phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark meal, wood meal and nutshell meal, cellu-lose powder or other solid carriers.

The formulations in general contain from 0.1 to 95 % by weight, 45 preferably from 0.5 to 90 ~ by weight, of one of the compounds I
or II or I or III or the mixture of the compounds I and II or I
and III. The active compounds are in this case employed in a BASF Aktiengesellschaft 931555 O.Z. 0050/44661 -- 2139~81 purity of from 90 % to 100 %, preferably from 95 % to 100 % (ac-cording to NMR spectrum or HPLC).

The compounds I or II or I or III and the mixtures or the corre-5 sponding formulations are applied by treating the harmful fungi or the plants, seeds, soils, surfaces, materials or spaces to be kept free from them with a fungicidally active amount of the mix-ture, or of the compounds I and II or I and III in the case of separate application. Application can be carried out before or 10 after attack by the harmful fungi.

Examples of the synergistic action of the mixtures according to the invention against harmful fungi.

15 It was possible to show the fungicidal action of the compounds and of the mixtures by the following tests:

The active compounds were prepared separately or jointly as a 20%
strength emulsion in a mixture of 70% by weight of cyclohex-20 anone, 20% by weight of Nekanil~ LN (Lutensol~ AP6, wetting agenthaving emulsifier and dispersant action based on ethoxylated al-kylphenols) and 10% by weight of Emulphor~ EL (Emulan~ EL, emul-sifier based on ethoxylated fatty alcohols) and accordingly diluted to the desired concentration with water.
Assessment followed determination of the attacked leaf areas in percent. These percentage values were converted into degrees of action. The degrees of action of the active compound mixtures to be expected were determined according to the Colby formula 30 [R.S. Colby, Weeds 15, (1967) 20-22] and compared with the de-grees of action observed.

Colby formula:

E = x + y - x X y/100 E is the degree of action to be expected, expressed in % of the untreated control, when using the mixture of the active compounds A and B in the concentrations a and b x is the degree of action, expressed in % of the untreated control, when using the active compound A in the concentration a BASF AXtiengesellschaft 931555 O.Z. 0050/44661 21392~:~

y is the degree of action, expressed in % of the untreated control, when using the active compound B in the concentration b 5 At a degree of action of 0, the attack of the treated plants cor-responds to that of the untreated control plants; at a degree of action of 100 the treated plants showed no attack.

Activity against Fusarium culmorum on wheat Primary leaves of wheat of the variety Kanzler which has been grown in pots were sprayed until dripping wet with aqueous spray liquor which contained 80% of active compound and 20% of emulsi-fier in the dry matter. On the following day, they were inocu-15 lated with a spore suspension of Fusarium culmorum and thenplaced in a climatic chamber having high atmospheric humidity (> 90%) at 22-24 C. After 6 days, the extent of symptom develop-ment was assessed visually.

Active compound Active compound con- Degree of action in centration in the % of the untreated spray liquor in ppm control Control (untreated) - O
25 I. 750 41 II. 750 0 Mixture according to degree of action degree of action 30 the invention observed calculated*) I + II 750 + 750 61 41 1:1 mixture I + II 500 + 500 41 21 1:1 mixture 35 I + II 750 + 75 41 21 10:1 mixture I + II 75 + 750 41 21 1:10 mixture BASF Aktiengesellschaft 931555 O.Z. 0050/44661 21392~1 -~ 8 Active compound Active compound con- Degree of action in centration in the ~ of the untreated spray liquor in ppm control Control (untreated) - o 5 I. 500 21 III. 500 o Mixture according to degree of action degree of action the inventionobserved calculated*) I + III 500 + 500 41 21 10 1:1 mixture I + III 500 + 50 41 21 10:1 mixture I + III 50 + 500 68 0 1:10 mixture *) calculated by the Colby formula From the results of the test it emerges that the degree of action observed in all mixture ratios is higher than the degree of action forecast by the Colby formula.

Claims (11)

1. A fungicidal mixture containing a) the oxime ether carboxamide of the formula I

and either b.1 the oxime ether carboxylic acid ester of the formula II

or b.2 the methoxyacrylic acid ester of the formula III

in a synergistically active amount.
2. A fungicidal mixture as claimed in claim 1, containing the oxime ether carboxamide of the formula I as claimed in claim 1 and the oxime ether carboxylic acid ester of the formula II as claimed in claim 1 in a synergistically active amount.
3. A fungicidal mixture as claimed in claim 1, containing the oxime ether carboxamide of the formula I as claimed in claim 1 and the methoxyacrylic acid ester of the formula III
as claimed in claim 1 in a synergistically active amount.
4. A fungicidal mixture as claimed in claim 1, wherein the weight ratio of the compound I to the compound II or the com-pound III is from 10:1 to 0.1:1.
5. A process for controlling harmful fungi, which comprises treating the harmful fungi, their environment or the plants, seeds, soils, surfaces, materials or spaces to be kept free from them with the compound of the formula I as claimed in claim 1 and the compound of the formula II as claimed in claim 1 or the compound of the formula I as claimed in claim 1 and the compound of the formula III as claimed in claim 1.
6. A process as claimed in claim 5, wherein the compound I as claimed in claim 1 and the compound II as claimed in claim 1 or the compound III as claimed in claim 1 are applied simul-taneously jointly or separately, or successively.
7. A process as claimed in claim 5, wherein the harmful fungi, their environment or the plants, seeds, soils, surfaces, ma-terials or spaces to be kept free from them are treated with from 0.005 to 0.5 kg/ha of the compound I as claimed in claim 1.
8. A process as claimed in claim 5, wherein the harmful fungi, their environment or the plants, seeds, soils, surfaces, ma-terials or spaces to be kept free from them are treated with from 0.01 to 0.5 kg/ha of the compound II as claimed in claim 1 or of the compound III as claimed in claim 1.
9. The use of the compound I as claimed in claim 1 for the pro-duction of fungicidally active synergistic mixtures as claimed in claim 1.
10. The use of the compound II as claimed in claim 1 for the pro-duction of fungicidally active synergistic mixtures as claimed in claim 1.
11. The use of the compound III as claimed in claim 1 for the production of fungicidally active synergistic mixtures as claimed in claim 1.
CA002139281A 1994-12-29 1994-12-29 Fungicidal mixtures Abandoned CA2139281A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA002139281A CA2139281A1 (en) 1994-12-29 1994-12-29 Fungicidal mixtures

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CA002139281A CA2139281A1 (en) 1994-12-29 1994-12-29 Fungicidal mixtures

Publications (1)

Publication Number Publication Date
CA2139281A1 true CA2139281A1 (en) 1996-06-30

Family

ID=4154957

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002139281A Abandoned CA2139281A1 (en) 1994-12-29 1994-12-29 Fungicidal mixtures

Country Status (1)

Country Link
CA (1) CA2139281A1 (en)

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