HK1022811B - Fungicidal active substance combinations - Google Patents

Description

Fungicidal active substance combinations

The present invention relates to active compound combinations which are very suitable for controlling phytopathogenic fungi, comprising compounds of the formula I and further known fungicidally active compounds.

It is known that the compounds of the formula I have fungicidal properties (DE-19602095). The activity of this compound is good, but its effect at low application rates is always unsatisfactory.

Furthermore, numerous pyrrole derivatives, aromatic carboxylic acid derivatives, morpholine compounds and other heterocycles are known to be useful for controlling fungi (cf.: Buchel, "Pflanzenschutz undSchadlinsbekampung", pages 87, 136, 140, 141 and 146 to 153, Georg Thieme Verlag, Stuttgart 1977). However, the activity of the compounds described is unsatisfactory at low application rates.

The present invention therefore provides novel active compound combinations comprising compounds of the formula IAnd at least one mixed component (A) propineb (Antrocol) and/or (B) benflurosulfamide (dichlorfluanide) and/or tolylfluanide (tolyfluoride) and/or (C) bitertanol and/or (D) tebuconazole and/or (E) triazolone and/or (F) triadimenol and/or (G) Imidacloprid and/or (H) procymidone and/or (II) mancozeb and/or (K) folpet and/or (L) dimethomorph and/or (M) cyazofamid and/or (N) metalaxyl and/or (O) fosetyl-Al and/or (P) famodone and/or (Q) tetramethol and/or (R) fosetyl-Al) and/or (P) fosetyl-xylene and/or (Q) pyrifenozide and/or (R) metrine and/or (R) metocloprid and/or (W) metocloprid and/or (V) metocloprid and/or (W) metoclopramide and/or (L) metocloprid and/or (M) prochloraz and/or (S) propineb and/or (S) and/or (W) propineb and/or (N) and/or (Y) fludioxonil and/or (Z) fenpiclonil andor (alpha) sitidine (Guazatine) and/or (beta) ethyl valacil and/or (chi) [ 2-methyl-1 [ [1- (4-methylphenyl) ethyl ] ethyl]Amino group]Carbonyl radical]Propyl radical]Carboxylic acid 1-methylethyl ester and/or (delta) 8-tert-butyl-2- (N-ethyl-N-N-propylamino) -methyl-1, 4-dioxaspiro [5, 4 ]]Decane and/or (. epsilon.) 2, 3-dichloro-4- (1-methylcyclohexylamido) -phenol and/or (. omega.) N- (R) - [1- (4-chlorophenyl) -ethyl]-2, 2-dichloro-1-ethyl-3 t-methyl-1 r-cyclopropanecarboxamide and/or (pi) fluazinam and/or (III) captan and/or (IV) pencycuron and/or (VI) fenpiclonil. The composition has very good fungicidal property, and the components complement each other to realize synergistic effect.

Active compounds of the formula I are known (DE 19602095). Other components in the compositions according to the invention are also known.

In addition to the active compounds of the formula I, the active compound compositions according to the invention comprise at least one active compound selected from the compounds (A) to (VI). Furthermore, further fungicidally active additives may additionally be present.

The synergistic effect of the compositions is particularly pronounced when the active compounds in the active compound compositions according to the invention are present in a certain weight ratio. However, the proportion by weight of active compound in the active compound composition can vary within a relatively wide range. In general, the parts by weight of active compounds (A) to (VI) are from 0.01 to 50, preferably from 0.25 to 20, per part by weight of active compound of the formula I.

In particular, the stated parts by weight of the following individual mixture components are, for each part of the compound of the formula I: (A) 1: 1 to 1: 50, preferably 1: 5 to 1: 20(B) 1: 1 to 1: 50, preferably 1: 1 to 1: 20(C) 10: 1 to 1: 10, preferably 5: 1 to 1: 5(D) 10: 1 to 1: 10, preferably 5: 1 to 1: 5(E) 10: 1 to 1: 10, preferably 5: 1 to 1: 5(F) 10: 1 to 1: 10, preferably 5: 1 to 1: 5(G) 20: 1 to 1: 20, preferably 10: 1 to 1: 10(H) 10: 1 to 1: 10, preferably 5: 1 to 1: 5(II) 1: 1 to 1: 50, preferably 1: 5 to 1: 20(K) 1: 1 to 1: 1, preferably 1: 5 to 1: 20(L) 10: 1 to 1: 10, preferably 5: 1 to 1: 5(M) 10: 1 to 1: 10, preferably 1: 5 to 1: 10 (K) 1: 1 to 1: 50, preferably 1: 5 to 1: 10 (N) 1: 1 to 1: 10, preferably 1: 5 to 1: 10 (O)10 to 1: 10, preferably 1: 10 (M)10 to 1: 10, preferably 1: 10 (N) 1: 1 to, preferably from 1: 1 to 1: 10(P) 10: 1 to 1: 10, preferably from 5: 1 to 1: 5(Q) 5: 1 to 1: 20, preferably from 1: 1 to 1: 10(R) 5: 1 to 1: 20, preferably from 1: 1 to 1: 10(S) 5: 1 to 1: 20, preferably from 1: 1 to 1: 10(T) 10: 1 to 1: 10, preferably from 5: 1 to 1: 5(U) 10: 1 to 1: 10, preferably from 5: 1 to 1: 5(V) 10: 1 to 1: 10, preferably from 5: 1 to 1: 5(W) 10: 1 to 1: 10, preferably from 5: 1 to 1: 5(X) 10: 1 to 1: 10, preferably from 5: 1 to 1: 5(Y) 10: 1 to 1: 10, preferably from 5: 1 to 1: 5(Z) 10: 1 to 1: 10, preferably from 5: 1 to 1: 10 (alpha) 10 to 1: 5 (beta) 10, preferably from 5: 1 to 1: 10, preferably from 5(Y)10 to 1: 1 to 1: 10, preferably from 5 (beta (50), preferably 20: 1 to 1: 10(χ) 10: 1 to 1: 10, preferably 5: 1 to 1: 5(δ) 10: 1 to 1: 20, preferably 5: 1 to 1: 10 (. epsilon.) 10: 1 to 1: 10, preferably 5: 1 to 1: 5 (. omega.) 10: 1 to 1: 10, preferably 5: 1 to 1: 5(π) 10: 1 to 1: 10, preferably 5: 1 to 1: 5(III) 5: 1 to 1: 50, preferably 1: 1 to 1: 20(IV) 10: 1 to 1: 10, preferably 4: 1 to 1: 4(VI) 10: 1 to 1: 10, preferably 4: 1 to 1: 4

The active compound combinations according to the invention have good fungicidal properties and can be used in particular for controlling phytopathogenic fungi, such as Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes, etc.

The active compound combinations according to the invention are particularly suitable for controlling cereal crop diseases, such as Erysiphe, Coccidioides, Sclerotium, Mucor, Septoria (Septoria spp.), Fusarium (Fusarium spp.), Pseudocercospora and Microcospora, and also for controlling fungal infections of non-cereal crops, such as wine, fruits, vegetables, such as Phytophthora, Plasmopara, Pythium, and Erysiphe, such as Sphingomonas or Undariomyces, and leaf spot disease-causing organisms, such as Venturia, Altemaria and Septoria, and Rhizoctonia, Botrytis, Sclerotium and Microsclerotium.

At the concentrations required for controlling plant diseases, the crop plants can have good tolerance to the active compound combinations. This fact allows us to treat aerial parts of plants, breeding stems and seeds, and the soil.

The active compound compositions according to the invention can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols and microcapsules and ultra-low-volume sprays, where the microcapsules are in a polymer and have a coating composition for the seed and an ULV formulation.

These formulations are prepared in a known manner, for example by mixing the active compounds or active compound combinations with extenders which are liquid solvents, pressurized liquefied gases, and/or solid carriers, and optionally with surfactants which are emulsifiers and/or dispersants, and/or foaming agents. If the filler used is water, it is possible to use, for example, organic solvents as auxiliaries. Basically, suitable solvent solutions include: aromatic compounds such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic compounds or chlorinated aliphatic hydrocarbons such as chlorobenzene, dichloroethane or dichloromethane, aliphatic hydrocarbons such as cyclohexane or paraffins (alkanes), for example petroleum fractions, alcohols such as butanol or ethylene glycol and ethers or esters thereof, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, or water. Liquefied gaseous extenders or carriers are liquids which are gaseous at ordinary temperature and pressure, for example aerosol propellants such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide. Suitable solid carriers are, for example, natural mineral powders such as kaolin, clay, talc, chalk, quartz, attapulgite (attapulgite), montmorillonite or kieselguhr and synthetic mineral powders such as fine silica powders, aluminas and silicates. Suitable solid carriers for the preparation of granules are: for example, screened crushed natural rocks such as calcite, marble, pumice, sepiolite and dolomite, or synthetic granules of inorganic or organic powders, and granules of organic materials such as sawdust, coconut shells, corn cobs and tobacco stalks. Suitable emulsifiers and/or foaming agents are, for example, nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, such as alkylaryl polyglycol ethers, alkylsulfonates, alkylsulfates, arylsulfonates or protein hydrolysates. Suitable dispersants are lignin-sulfite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and synthetic polymer powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate or natural phospholipids such as cephalins and lecithins and synthetic phospholipids, can be used. Other additives may be mineral and vegetable oils.

It is also possible to use colorants such as inorganic pigments, for example iron oxide, titanium tetroxide and Prussian blue, and organic dyes, for example alizarin dyes, azo dyes and metal phthalocyanine dyes, and also small amounts of nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

The formulations generally contain from 0.1 to 95% by weight of active compound, preferably from 0.5 to 90%.

The active compound combinations according to the invention can be used in various formulations as a mixture with other known active compounds, such as fungicides, insecticides, acaricides and herbicides, and also with fertilizers and plant growth regulators.

The active compound combinations can be used as such or in the form of ready-to-use solutions, emulsifiable concentrates, emulsions, suspensions, wettable powders, soluble powders and granules prepared therefrom.

They are used in the customary form, for example by watering, spraying, atomizing, broadcasting, spreading, treating a powder of dry seeds, treating a solution of seeds, treating a soluble powder of a slurry or applying the pesticide by cladding.

The active compound compositions in the form of their use can vary within considerable limits when treating parts of plants, and they are generally from 1 to 0.0001% by weight, preferably from 0.5 to 0.001%.

The treatment of seed usually requires from 0.001 to 50 g of active compound per kg of seed, preferably from 0.01 to 10 g.

For soil treatment, concentrations of active compound of from 0.00001 to 0.1% by weight, preferably from 0.0001 to 0.02%, are required at the site of use.

The active compound combinations according to the invention have a pronounced fungicidal synergistic activity according to the following examples. Although each active compound exhibits a weak fungicidal activity, the activity of the composition exceeds that of the simple sum of the activities of the individual compounds.

When the fungicidal activity of the active compound combinations exceeds the sum of the activities of the individual active compounds applied individually, then there is always a synergistic effect of the fungicides.

The expected activity of a given combination of two active compounds can be calculated according to the following formula (cf. Colby, s.r., "calculating synergistic and antagonistic activity of herbicides", "weeds" stages 15, pages 20 to 22, 1976):

if it is not

X is whenmppm concentration% of effect when applying active compound A,

y is such asnppm concentration the percentage of effect of active compound B applied,

e is when each ismppm andnppm concentration the percentage of effect of the active compounds A and B applied,

then

E＝X+Y-(X·Y)/100

If the actual fungicidal activity exceeds the calculated value, the activity of the composition is super-additive, i.e. there is a synergistic effect. In this case, the actually observed effect must be larger than the expected effect value (E) calculated by the above equation. Example 1 Phytophthora (tomato) test/protective Activity

To determine the protective activity, commercial preparations of the active compounds are sprayed at the stated application rates onto young plants. After the spray layer has dried, an aqueous spore suspension of potato late blight (phytophthora infestans) is inoculated onto the plants. The plants were stored in an incubator at 20 ℃ and 100% relative air humidity.

The assay was performed three days after inoculation. 0% means the effect of the control, 100% means no infection.

The active compound combinations according to the invention have a pronounced fungicidal synergistic activity according to the following examples. Although each active compound exhibits a weak fungicidal activity, the activity of the composition exceeds that of the simple sum of the activities of the individual compounds.

When the fungicidal activity of the active compound combinations exceeds the sum of the activities of the individual active compounds applied individually, then there is always a synergistic effect of the fungicides.

The expected activity of a given combination of dual active compounds can be calculated according to the following formula (cf. Colby, s.r., "calculating synergistic and antagonistic activity of herbicides", "weeds" stage 15, pages 20-22, 1976):

if it is not

X is whenmppm concentration% of effect when applying active compound A,

y is such asnppm concentration the percentage of effect of active compound B applied,

e is when each ismppm andnppm concentration percent effect when applying active compound A,

then

E＝X+Y-(X·Y)/100

If the actual fungicidal activity exceeds the calculated value, the activity of the composition is super-additive, i.e. there is a synergistic effect. In this case, the actually observed effect must be larger than the expected effect value (E) calculated by the above equation.

The following table clearly shows that the actual activity of the active compound compositions according to the invention is greater than the calculated activity, i.e. that there is a synergistic effect.TABLE 1Phytophthora assay (tomato)/amount of active compound(s) which protect the active compound(s) administered in g/ha units of effect% (I) 0.59(χ) 0.5 20Racemic amides of L-valineMixtures according to the invention

Actual Effect of active Compounds on mixing ratio Using amount calculated by Colby formula (g/ha) expected value
	(I) 0.5} + } 77 27(χ) 1∶1 0.5

TABLE 1-Phytophthora continentalis determination (tomato)/amount of active compound(s) which protect the active compound(s) administered in g/ha units (I) 545Tebuconazole (D) 526Mixtures according to the invention

Actual Effect of active Compounds on mixing ratio Using amount calculated by Colby formula (g/ha) expected value
	(I) 5} 1∶1 + } 84 59(D) 5

TABLE 1-Phytophthora continentalis determination (tomato)/amount of active compound(s) which protect the active compound(s) administered in g/ha units (I) 545Triadimenol (F) 50Mixtures according to the invention

Actual Effect of the amount of active Compound applied (g/ha) on the mixing ratio the expected value calculated using the Colby formula
	(I) 5} 1∶1 + } 72 45(F) 5

TABLE 1-Phytophthora continentalis determination (tomato)/amount of active compound(s) which protect the active compound(s) administered in g/ha units (I) 5 45(ε) 5 14Mixtures according to the invention

Actual Effect of active Compounds on Mixed proportions Using the amount of expected value calculated by the Colby formula (g/ha)
	(I) 5} 1∶1 + } 82 53(F) 5

TABLE 1-Phytophthora continentalis determination (tomato)/amount of active compound(s) which protect the active compound(s) administered in g/ha units (I) 545(ω) 5 3Mixtures according to the invention

Actual Effect of active Compounds on Mixed proportions expected application rates (g/ha) calculated using the Colby formula
	(I) 5} 1∶1 + } 71 47(ω) 5

TABLE 1-Phytophthora continentalis determination (tomato)/amount of active compound(s) which protect the active compound(s) administered in g/ha units (I) 545(H) 5 34Mixtures according to the invention

Actual Effect of active Compounds on Mixed proportions Using the amount of expected value calculated by the Colby formula (g/ha)
	(I) 5+ } 1: 1+ } 7564 procymidone 5

TABLE 1-Phytophthora continentalis determination (tomato)/amount of active compound(s) which protect the active compound(s) administered in g/ha units (I) 545Mancozeb (II) 5054Mixtures according to the invention

Active combination in mixed ratioActual effect of the application Using the amount (g/ha) predicted by the Colby formula
	(I) 5+ } 1: 10 + } 8975 mancozeb (II) 50

TABLE 1-Phytophthora continentalis determination (tomato)/amount of active compound(s) which protect the active compound(s) administered in g/ha units (I) 120Folpet (K) 1027Mixtures according to the invention

Actual Effect of active Compounds on mixing ratio Using amount calculated by Colby formula (g/ha) expected value
	(I) 1+ } 1: 10 + } 7442 folpet 10

TABLE 1-Phytophthora continentalis determination (tomato)/amount of active compound(s) which protect the active compound(s) administered in g/ha units (I) 120Dimethomorph (L)10Mixtures according to the invention

Actual Effect of Mixed ratio active Compound application Using expected values of calculated amounts (g/ha) of Colby formula
	(I) 1+ } 1: 10 + } 4920 Dimethomorph (L)1

TABLE 1-Phytophthora continentalis determination (tomato)/amount of active compound(s) which protect the active compound(s) administered in g/ha units (I) 545Cymoxanil (M) 512Mixtures according to the invention

Actual Effect of active Compounds on Mixed proportions expected application rates (g/ha) calculated using the Colby formula
	(I) 5+ } 1: 1+ } 7852 cymoxanil 5

TABLE 1-Phytophthora continentalis determination (tomato)/amount of active compound(s) which protect the active compound(s) administered in g/ha units (I) 5 45Metalaxyl (N) 51Mixtures according to the invention

Actual Effect of active Compounds on Mixed proportions Using the amount of expected value calculated by the Colby formula (g/ha)
	(I) 5+ } 1∶1 + }62 46(N) 5

TABLE 1-Phytophthora continentalis determination (tomato)/amount of active compound(s) which protect the active compound(s) administered in g/ha units (I) 545Fluazinam (pi) 511Mixtures according to the invention

Actual Effect of active Compounds on mixing ratio Using amount calculated by Colby formula (g/ha) expected value
	(I) 5+ } 1∶1 + }85 51 fluazinam (pi) 5

TABLE 1-Phytophthora continentalis determination (tomato)/amount of active compound(s) which protect the active compound(s) administered in g/ha units (I) 545Cyprodinyl(R) 5 0Mixtures according to the invention

Actual Effect of Mixed ratio active Compound application Using the amount calculated by the Colby formula (g/ha) expected value
	(I) 5+ } 1∶1 + }62 45Cyprodinyl 5

TABLE 1-Phytophthora continentalis determination (tomato)/amount of active compound(s) which protect the active compound(s) administered in g/ha units (I) 120Kresoximemethyl(T) 1 14Mixtures according to the invention

Actual Effect of active Compounds on the mixing ratios expected from the application in Colby (g/ha) is used
	(I) 1+ } 1∶10 + }64 31Kresoximemethyl(T) 1

TABLE 1-Phytophthora continentalis determination (tomato)/amount of active compound(s) which protect the active compound(s) administered in g/ha units (I) 545Ethyl Guthion 50 Bendicar (beta)Mixtures according to the invention

Actual Effect of active Compounds on mixing ratio expected value calculated using Colby formula amount (g/ha)
	(I) 5+ } 1: 1+ } 5445 Ethyl Valufos (/3) 5

Example 2 Monomycesium (cucumber) assay/protective Activity

To determine the protective activity, commercial preparations of the active compounds are sprayed onto young plants at the stated application rates. After the spray coating has dried, an aqueous spore suspension of cucumber powdery mildew (sphaerothecafeuliginea) is inoculated on the plants. Plants were kept in the greenhouse at 23 ℃ and 70% relative air humidity.

Ten days after inoculation the assay was performed. 0% means the effect of the control, 100% means no infection.

The active compound combinations according to the invention have a pronounced fungicidal synergistic activity according to the following examples. Although each active compound exhibits a weak fungicidal activity, the activity of the composition exceeds that of the simple sum of the activities of the individual compounds.

When the fungicidal activity of the active compound combinations exceeds the sum of the activities of the individual active compounds applied individually, then there is always a synergistic effect of the fungicides.

The expected activity of a given combination of dual active compounds can be calculated according to the following formula (cf. Colby, s.r., "calculating synergistic and antagonistic activity of herbicides", "weeds" stage 15, pages 20-22, 1976):

if it is not

X is whenmppm concentration% of effect when applying active compound A,

y is such asnppm concentration the percentage of effect of active compound B applied,

e is when each ismppm andnppm concentration the percentage of effect of the active compounds A and B applied,

then

E＝X+Y-(X·Y)/100

If the actual fungicidal activity exceeds the calculated value, the activity of the composition is super-additive, i.e. there is a synergistic effect. In this case, the actually observed effect must be larger than the expected effect value (E) calculated by the above equation.

The following table clearly shows that the actual activity of the active compound compositions according to the invention is greater than the calculated activity, i.e. that there is a synergistic effect.TABLE 2Monochaeta assay (yellow)Melon)/protective active Compound application rates, in g/ha units of effect% (I) 2.522Propineb (A) 2545

n＝＞1Mixtures according to the invention

Actual Effect of Mixed ratio active Compound application Using the amount calculated by the Colby formula (g/ha) expected value
	(I) 2.5} 1: 10 + } 7756 propineb 25

TABLE 2-Pericarispora determination (cucumber)/amount of active compound(s) applied in g/ha units of effect% (I) 2.522Phenoxy sulfonamide (B1) 2520Mixtures according to the invention

Actual Effect of active Compounds on Mixed proportions Using the amount of expected value calculated by the Colby formula (g/ha)
	(I) 2.5} 1∶10 + }57 3825

TABLE 2-Pericarispora determination (cucumber)/amount of active compound(s) applied in g/ha units of effect% (I) 2.522Methylphenylfluorosulfonamide (B2) 2522Mixtures according to the invention

Actual Effect of the amount of active Compound applied in Mixed proportion Using the expected value (g/ha) calculated using the Colby formula
	(I) 2.5} 1∶10 + }57 3925

TABLE 2-Pericarispora determination (cucumber)/amount of active compound(s) applied in g/ha units of effect% (I) 2.522Bisbenzotriazolol (C) 2.520Mixtures according to the invention

Actual Effect of Mixed ratio active Compound application Using the amount calculated by the Colby formula (g/ha) expected value
	(I) 2.5+ } 1: 1+ } 5038 bis-benzenetriazolol 2.5

TABLE 2-Pericarispora determination (cucumber)/amount of active compound(s) applied in g/ha units of effect% (I) 2.522Triazolones (E) 2.530Mixtures according to the invention

Actual Effect of active Compounds on mixing ratio Using amount calculated by Colby formula (g/ha) expected value
	(I) 2.5} 1: 1+ } 6745 triazolones (E) 2.5

TABLE 2-Diapause monococcum assay (cucumber)/protective ActivityThe amount of active compound applied, in g/ha units, (I) 2.522(δ) 2.5 10Mixtures according to the invention

Actual Effect of active Compounds on Mixed proportions expected application rates (g/ha) calculated using the Colby formula
	(I) 2.5+ } 1∶1 + }70 30(δ) 2.5

TABLE 2-Pericarispora determination (cucumber)/amount of active compound(s) applied in g/ha units of effect% (I) 2.522Captan (III) 12.50Mixtures according to the invention

Actual Effect of Mixed ratio active Compound application Using the amount calculated by the Colby formula (g/ha) expected value
	(I) 2.5+ } 1: 5+ } 6322 captan 12.5

TABLE 2-Pericarispora determination (cucumber)/amount of active compound(s) applied in g/ha units of effect% (I) 2.522Pyrimethanil(Q) 12.5 10Mixtures according to the invention

Actual Effect of active Compounds on mixing ratio Using amount calculated by Colby formula (g/ha) expected value
	(I) 2.5+ }1∶5 + }57 30Pyrimethanil 12.5

TABLE 2-Pericarispora determination (cucumber)/amount of active compound(s) applied in g/ha units of effect% (I) 2.522azoxystrobin(U) 2.5 57Mixtures according to the invention

Actual Effect of active Compounds on mixing ratio Using amount calculated by Colby formula (g/ha) expected value
	(I) 2.5+ } 1∶1 + }83 66azoxystrobin 2.5

Example 3 Botrytis (Soybean) assay/protective Activity

To determine the protective activity, commercial preparations of the active compounds are sprayed onto young plants at the stated application rates. After the sprayed layer had dried, two small pieces of agar covered with soybean downy mildew (Botrytis cinerea) were placed on each leaf. The plants were placed in a black room at 20 ℃ and 100% relative air humidity.

Infected leaf spot sizes were determined two days after inoculation. 0% means the effect of the control, 100% means no infection.

The active compound combinations according to the invention have a pronounced fungicidal synergistic activity according to the following examples. Although each active compound exhibits a weak fungicidal activity, the activity of the composition exceeds that of the simple sum of the activities of the individual compounds.

When the fungicidal activity of the active compound combinations exceeds the sum of the activities of the individual active compounds applied individually, then there is always a synergistic effect of the fungicides.

The expected activity of a given combination of dual active compounds can be calculated according to the following formula (cf. Colby, s.r., "calculating synergistic and antagonistic activity of herbicides", "weeds" stage 15, pages 20-22, 1976):

if it is not

X is whenmppm concentration application activationThe percentage of the effect of compound a,

y is such asnppm concentration the percentage of effect of active compound B applied,

e is when each ismppm andnppm concentration the percentage of effect of the active compounds A and B applied,

then

E＝X+Y-(X·Y)/100

If the actual fungicidal activity exceeds the calculated value, the activity of the composition is super-additive, i.e. there is a synergistic effect. In this case, the actually observed effect must be larger than the expected effect value (E) calculated by the above equation.

The following table clearly shows that the actual activity of the active compound compositions according to the invention is greater than the calculated activity, i.e. that there is a synergistic effect.TABLE 3Botrytis assay (soya)/protective active Compound application amount in g/ha Effect%

50 15Ethanophosphonium (O) 2504Mixtures according to the invention

Actual Effect of Mixed ratio active Compound application Using expected values of calculated amounts (g/ha) of Colby formula
	(I) 50+ } 1: 5+ } 5518 fosetyl-aluminum 250

Example 4Fusarium (Fusarium nivale) assay (triticale)/seed treatment

The active compound is used as a dry seed coating. The active compounds are each filled with mineral powder to give a fine mixture powder, which ensures uniform distribution on the seed surface.

To coat the seeds, the infected seeds were shaken in a sealed glass bottle for three minutes together with the seed coating.

2X 100 triticale plants were sown in standard soil at a depth of one centimeter and placed on seed trays, and cultured in a greenhouse at about 10 ℃ and about 95% relative air humidity, with 15 hours of light per day.

After three weeks of sowing, the plants were assayed for snow mold symptoms. 0% refers to untreated control effect, 100% refers to no disease infection.Watch fourFusarium assay (triticale)/seed treatment active Compound Effect on seed%

Is administered in mg/kg

75 93

2589 Tebuconazole (O) 2520

2520 Triazolol (F) 2552Watch fourActive Compounds Effect of active Compounds on seeds%

The administration amount mg/kg pencycuron IV 2529Fenpiclonil (V) 7567fludioxonil(Y) 75 92Watch fourActive Compounds Effect of application of active Compounds on seeds%

In mg/kg of (I) 12.597 (V) +12.5

97(I) 12.5(F) +12.5

93(I) 12.5+ Penicillin +12.5

100(I) 37.5(V) +37.5

99(I) 37.5(Y) +37.5Example 5Rhizoctonia solani (Rhizoctonia solani) assay (cotton)/seed treatment

The active compound is used as a dry seed coating. The active compounds are each filled with mineral powder to give a fine mixture powder, which ensures uniform distribution on the seed surface.

To coat the seeds, the infected seeds were shaken in a sealed glass bottle for three minutes together with the seed coating.

2X 100 seeds were sown in a depth of two centimeters of standard soil infected with Rhizoctonia solani and placed on seed trays, and cultured in a greenhouse at about 22 ℃ with 15 hours of light each day.

Eight days after sowing, the measurement was carried out. 0% refers to untreated control effect, 100% refers to no disease infection.Watch fiveDetermination of the Effect of active Compounds on seeds of the seed treatment (Cotton)/seed treatment active Compounds%

The administration amounts mg/kg (I) 7516Triadimenol (F) 7548According to the inventionMing's mixture(I) 37.5(F) + 37.563 example 6 Erysiphe assay (barley)/therapeutic action solvent: 25 parts of N, N-dimethylacetamide by weight of an emulsifier: alkylaryl polyglycol ether 0.6 weight portions

To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated solvents and emulsifiers and the concentrate is diluted with water to the desired concentration.

To determine the therapeutic effect, young plants were dusted with powdery mildew f.sp.hordei spore powder. 48 hours after inoculation, the active compound preparation is sprayed onto the crop plants at the stated application rate.

The crops are placed in a greenhouse, and the temperature is 20 ℃, the relative humidity is about 80 percent, so that the growth of mildew stains can be promoted.

Seven days after inoculation the assay was performed. 0% refers to untreated control effect, 100% refers to no disease infection. TABLE 6 powdery mildew assay (barley)/therapeutic Effect

Active compound	Application amount g/ha of active compound	Good effect%
			Known as (I) (D) (F) (V) (W) (T) (delta)	2512.56.25256.256.2512.56.2512.56.25	753308333679233670
The mixtures according to the invention (I) + (D) (I) + (F) (I) + (T) (I) + (V) (I) + (W) (I) + (delta)	6.25+18.753.125+3.12518.75+6.251.563+4.6876.25+6.253.125+9.3759.375+3.1256.25+6.253.125+9.3751.563+4.6873.125+3.1251.563+4.687	100759283758383100100675083

Example 7 erysiphe (wheat)/treatment effect solvent: 25 parts of N, N-dimethylacetamide by weight of an emulsifier: alkylaryl polyglycol ether 0.6 weight portions

To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated solvents and emulsifiers and the concentrate is diluted with water to the desired concentration.

To determine the therapeutic effect, young plants were dusted with Erysiphe graminis f.sp. 48 hours after inoculation, the active compound preparation is sprayed onto the crop plants at the stated application rate.

The crops are placed in a greenhouse, and the temperature is 20 ℃, the relative humidity is about 80 percent, so that the growth of mildew stains can be promoted.

Seven days after inoculation the assay was performed. 0% refers to untreated control effect, 100% refers to no disease infection. TABLE 7 powdery mildew determination (barley)/therapeutic Effect

Active compound	Application amount g/ha of active compound	Good effect%
			Known as (I) (T) (R) (Y)	256.256.252525	3300170
The mixtures (I) + (T) (I) + (R) (I) + (Y) according to the invention	3.125+3.1254.6875+1.562512.5+12.518.75+6.256.25+18.7518.75+6.25	505075505050

Example 8 wheatLeukoderma (leukoderma nodorum) assay (wheat)/treatment solvent: 25 parts of N, N-dimethylacetamide by weight of an emulsifier: alkylaryl polyglycol ether 0.6 weight portions

To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated solvents and emulsifiers and the concentrate is diluted with water to the desired concentration.

To determine the therapeutic effect, a conidia suspension of Leptosphaeria nodorum was sprayed onto the crop seedlings. The crops are stored at 20 ℃ and 100% relative humidity in an incubator for 48 hours, after which the active compound preparation is sprayed onto the crops at the stated application rate.

The crops were placed in a greenhouse at a temperature of 15 ℃ and a relative humidity of about 80%.

Ten days after inoculation, the assay was performed. 0% refers to untreated control effect, 100% refers to no disease infection. TABLE 8 wheat leukoderma determination (wheat)/treatment Effect

Active compound	Application amount g/ha of active compound	Good effect%
			Known as (I) (F) (W) (T) (delta) (R)	12.56.256.2512.512.512.56.25	62622525502550
The mixtures (I) + (F) (I) + (W) (I) + (T) (I) + (delta) (I) + (R) according to the invention	4.6875+1.56259.375+3.1259.375+3.1259.375+3.1251.5625+4.6875	7575757575

Example 9 nucleocapsid (pyrenophora teres) assay (barley)/treatment solvent: n, N-dimethylacetamide 25 parts by weight of emulsifier: alkylaryl polyglycol ether 0.6 weight portions

To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated solvents and emulsifiers and the concentrate is diluted with water to the desired concentration.

To determine the therapeutic effect, conidia suspensions of the genus Pyrenophora teres were sprayed onto crop seedlings. The crops are stored at 20 ℃ and 100% relative humidity in an incubator for 48 hours, after which the active compound preparation is sprayed onto the crops at the stated application rate.

The crops were placed in a greenhouse at a temperature of 20 ℃ and a relative humidity of about 80%.

Seven days after inoculation the assay was performed. 0% refers to untreated control effect, 100% refers to no disease infection. TABLE 9

Active compound	Application amount g/ha of active compound	Good effect%
			Known as (I) (F)	6.256.25	00
The mixtures (I) + (F) according to the invention	4.6875+1.5625	50

Example 10 puccinia assay (wheat)/treatment effect solvent: 25 parts of N, N-dimethylacetamide by weight of an emulsifier: alkylaryl polyglycol ether 0.6 weight portions

To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated solvents and emulsifiers and the concentrate is diluted with water to the desired concentration.

To determine the therapeutic effect, a conidia suspension of wheat leaf rust (Puccinia recondita) was sprayed to the plant seedlings. The crops are stored at 20 ℃ and 100% relative humidity in an incubator for 48 hours, after which the active compound preparation is sprayed onto the crops at the stated application rate.

The crops were placed in a greenhouse at a temperature of 20 ℃ and a relative humidity of about 80%.

Ten days after inoculation, the assay was performed. 0% refers to untreated control effect, 100% refers to no disease infection. TABLE 10 leaf rust assay (wheat)/treatment Effect

Active compound	Application amount g/ha of active compound	Good effect%
			Known as (I) (W) (R)	6.256.256.25	675033
The mixtures (I) + (W) (I) + (R) according to the invention	4.6875+1.56253.175+3.125	8375

Example 11 Erysiphe assay (wheat)/protective solvent: 25 parts of N, N-dimethylacetamide by weight of an emulsifier: alkylaryl polyglycol ether 0.6 weight portions

To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated solvents and emulsifiers and the concentrate is diluted with water to the desired concentration.

To determine the protective effect, the active compound preparations are sprayed at the stated application rates onto the crop plants.

After the spray coating has dried, spores of the cereal powdery mildew (Erysiphe graminis f.sp.tritici) are sprinkled on the crop.

The growth of mildew stains can be promoted by storing the crops in an incubator at 20 ℃ and a relative humidity of 80%.

Seven days after inoculation the assay was performed. 0% refers to untreated control effect, 100% refers to no disease infection. TABLE 11 Erysiphe determination (wheat)/therapeutic Effect

Active compound	Application amount g/ha of active compound	Good effect%
			Known as (I) (D) (W) (T) (delta) (R)	2512.56.256.256.25256.2512.5	7929004386140
The mixtures according to the invention (I) + (D) (I) + (W) (I) + (T) (I) + (delta) (I) + (R)	1.5625+4.68754.6875+1.56256.25+18.753.125+3.1251.5625+4.68754.6875+1.56253.125+9.375	71579357795757

Example 12 wheat leukoderma (Leptosphaeria nodorum) assay (wheat)/protective solvent: 25 parts of N, N-dimethylacetamide by weight of an emulsifier: alkylaryl polyglycol ether 0.6 weight portions

To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated solvents and emulsifiers and the concentrate is diluted with water to the desired concentration.

To determine the protective effect, the active compound preparations are sprayed at the stated application rates onto the crop plants. After the spray coating has dried, a spore suspension of vitiligo (Leptosphaeria nodorum) in wheat is sprayed onto the crop. The crops were stored in an incubator at 20EC and 80% relative humidity for 48 hours.

The crop is placed in a greenhouse at a temperature of 15 ℃ and a relative humidity of 80%.

Measurements were taken 10 days after inoculation. 0% refers to untreated control effect, 100% refers to no disease infection. TABLE 12 wheat leukoderma (wheat)/protective action

Active compound	Application amount g/ha of active compound	Good effect%
			Known as (I) (D) (F) (V) (W) (T) (delta) (R) (Y)	6.256.256.256.256.256.256.256.256.25	2525050500252525

TABLE 12 wheat leukoderma determination (wheat)/protection

Active compound	Application amount g/ha of active compound	Good effect%
			The mixtures according to the invention (I) + (D) (I) + (F) (I) + (V) (I) + (W) (I) + (T) (I) + (delta) (I) + (R) (I) + (Y)	3.125+3.1254.6875+1.56251.5625+4.68751.5625+4.68753.125+3.1254.6875+1.56251.5625+4.68754.6875+1.56253.125+3.1251.5625+4.68754.6875+1.56253.125+3.1251.5625+4.68754.6875+1.5625	505050100100507510010010010075100100

Example 12 Puccinia assay (wheat)/protective solvent: 25 parts of N, N-dimethylacetamide by weight of an emulsifier: alkylaryl polyglycol ether 0.6 weight portions

To produce a suitable preparation of active compound, 1 part by weight of active compound or active compound combination is mixed with the stated solvents and emulsifiers and the concentrate is diluted with water to the desired concentration.

To determine the protective effect, the active compound preparations are sprayed at the stated application rates onto the crop plants. After the spray layer has dried, a conidia suspension of wheat leaf rust (Puccinia recondita) is sprayed onto the crop. The crops were stored in an incubator at 20 ℃ and 100% relative humidity for 48 hours.

The crop is placed in a greenhouse at the temperature of 20 ℃ and the relative humidity of 80 percent, so that the rust spots can be promoted to grow.

Measurements were taken 10 days after inoculation. 0% refers to untreated control effect, 100% refers to no disease infection. TABLE 13 leaf rust assay (wheat)/protective Effect

(Single) active Compounds	Application amount g/ha of active compound	Good effect%
			Known as (I) (D) (F) (V) (W) (T) (delta) (R) (Y)	6.256.256.256.256.256.256.256.256.25	813813817525131313

TABLE 13 Puccinia assay (wheat)/treatment Effect

Active compound	Application amount g/ha of active compound	Good effect%
			The mixtures according to the invention (I) + (D) (I) + (F) (I) + (V) (I) + (W) (I) + (T) (I) + (delta) (I) + (R) (I) + (Y)	3.125+3.1251.5625+4.68754.6875+1.56253.125+3.1253.125+3.1251.5625+4.68754.6875+1.56253.125+3.1251.5625+4.68754.6875+1.56254.6875+1.56253.125+3.1251.5625+4.68754.6875+1.56253.125+3.1251.5625+4.68754.6875+1.56253.125+3.1251.5625+4.68754.6875+1.5625	94948888881008810088100100100941009410010010094100

Claims (6)

1. A fungicidal composition comprising a compound of formula (I) and at least one of the following components:(A) propineb (Antrocol) and/or (B) benfluranide (dichlorfluanide) and/or tolylfluanide (tollyfluanide) and/or (C) bitertanol and/or (D) tebuconazole and/or (E) triadimefon and/or (F) triadimenol and/or (G) imidacloprid and/or (H) procymidone and/or (II) mancozeb and/or (K) folpet and/or (L) dimethomorph and/or (M) cyanamide and/or (N) metalaxyl and/or (O) aluminium ethiolate (fosetyl-Al) and/or (K) folpet and/or (L) dimethomorph(Q) pyrimethanil and/or (R) cypridinyl and/or (S) mepanipyrim and/or (T) kresoxim-methyl and/or (U) azoxystrobin and/or (V) epoxyconazole and/or (W) metconazole and/or (X) fluoroquinconazole and/or (Y) fluoroxonil and/or (Z) fenpiclonil and/or (alpha) orydine and/or (beta) ethylorythion and/or (chi) [ 2-methyl-1 [ [ [1- (4-methylphenyl) ethyl ] propyl]Amino group]Carbonyl radical]Propyl radical]Carboxylic acid 1-methylethyl ester and/or (delta) 8-tert-butyl-2- (N-ethyl-N-N-propylamino) -methyl-1, 4-dioxaspiro [5, 4 ]]Decane and/or (. epsilon.) 2, 3-dichloro-4- (1-methylcyclohexylamido) -phenol and/or (. omega.) N- (R) - [1- (4-chlorophenyl) -ethyl]-2, 2-dichloro-1-ethyl-3 t-methyl-1 r-cyclopropaneamide and/or (pi) fluazinam and/or (III) captan and/or (IV) pencycuron and/or (VI) fenpiclonil; and the weight ratio of the active compound of the formula (I) to the active compounds of the abovementioned (A) to (IV) in the abovementioned compositions is from 1: 0.01 to 1: 50.

2. Fungicidal compositions according to claim 1, characterized in that the weight ratio of the active compounds of the formula I to the active compounds of (a) to (VI) in each case in the fungicidal compositions is from 1: 0.25 to 1: 20.

3. The fungicidal composition of claim 1 or 2, further comprising a common component for fungicidal compositions.

4. A method for controlling fungi, characterized in that a fungicidal composition according to any of claims 1 to 3 is allowed to act on the fungi and/or their growing environment.

5. Use of the fungicidal composition according to any of claims 1 to 3 for controlling fungi.

6. A process for preparing the fungicidal compositions according to any of claims 1 to 3, characterized in that the active compounds according to claim 1 are mixed with extenders and/or surfactants.