DD251277A5 - FUNGICIDAL AGENT - Google Patents

Abstract

The invention relates to fungicidal agents for the fight against phytopathogenic fungi in horticulture and agriculture. The aim of the invention is the provision of new agents with a strong fungicidal action, which ensure a good fight against phytopathogenic fungi with lower application rates. According to the invention triazolyl-metal complexes of general formula I are used as active ingredient in the new fungicidal agents, in which for example mean: Me copper, zinc, manganese, tin, magnesium, XHalogen, Qein grouping CO or CH (OH), Y1Halogen, alkoxycarbonyl, nitro or a sulfo group, Y 2 hydrogen, halogen or hydroxy, n and m 0, 1 or 2, k and 1, 2, 3 or 4, p are the integers between 0 and 6. Formula (I)

Description

CH.

OCO

.PH "O

(D,

in which

Me stands for copper, zinc, manganese, tin, magnesium, X stands for halogen,

Q stands for a grouping CO or CH (OH),

y ^{1 is} halogen, alkoxycarbonyl, nitro or a sulfo group,

y ^{2 is} hydrogen, halogen or hydroxy, η and m are 0.1 or 2,

kund 11,2,3 or4 mean,

p represents the integers between 0 and 6 in addition to extenders and / or surface-active agents,

2. A method for controlling phytopathogenic fungi, characterized by allowing compounds of the general formula I according to item 1 to act on the fungi or their habitat.

3. A process for the preparation of fungicidal agents, characterized by mixing compounds of the general formula I according to item 1 with extenders and / or surface-active agents.

Field of application of the invention

The invention relates to fungicidal compositions containing triazolymetal complexes for use in the control of phytopathogenic fungi in horticulture and agriculture.

Characteristic of the known technical solutions

It is known that certain 1,2,4-triasol derivatives, such as. B. i-fi ^ AT

and its complex with copper (II) chloride (molar ratio 2: 1) are fungicidally effective (cf. DE-OE-PS 2201063, DE

OS 2423987, HU-PS 165782 and HU-PS 171714).

It is also known that triasol derivatives of the general formula II

* '· CH,

- 0 - CH. - Q - C '- CH ₃

(II)

CH.

which can be used according to the invention as starting material are fungicidally effective. The effect and that

However, the spectrum of activity of these compounds is not always fully satisfactory, especially at low use levels and concentrations.

Finally, it is known that complexes of triazole derivatives of general formula II with metal halides, in particular with metal chlorides, are fungicidally active (compare DE-OS 2423987 or HU-PS 171714). These complexes contain at least 80% triazole derivative, which means a maximum of 20% triazole derivatives. The effect of these complexes is very low on open fields despite the good results in glasshouses, and therefore the use of these agents could not spread.

Object of the invention

The aim of the invention is to provide novel compounds with a strong fungicidal action, in which even low application rates are sufficient for a successful control of phytopathogenic fungi.

Explanation of the essence of the invention

The invention has for its object to find new compounds with the desired properties, which are suitable as active ingredient in fungicidal agents.

According to the invention, new triazolyl metal complexes are made available as active ingredient in fungicidal agents, whereby the use of triazole derivatives can be reduced by 40 to 50%. This makes it possible to replace the economically very accessible triazole derivatives by cheap metal salts and to reduce the burden of nature on active triazole derivatives.

The action of the novel compounds is satisfactory in controlling phytopathogenic fungi even at low use levels and use levels.

The new triazolyl metal complexes according to the invention correspond to the general formula I.

Μβ -

CH.

- O-CH-Q-C-CH.

CH.

OCO

in which Me stands for copper, zinc, manganese, tin or magnesium,

X is halogen,

Q is the group CO or C (OH) H, Y ^{1 is} halogen, alkoxycarbonyl, nitro or a sulphon group, Y ^{2 is} hydrogen, halogen, or hydroxyl, η and m are 0,1 or 2,

kundl 1,2,3 or4 mean, ρ stands for the integers between 0 and 6.

Furthermore, it has been found that the novel triazolyl metal complexes of the general formula I are obtained when triazole derivatives of the general formula II in which X, Q and η have the meanings given above, with metal salts of aromatic carboxylic acids of the general formula III

OCO

in which Me, y ¹ , y ² , 1, m and ρ have the meanings given above, in the presence of a diluent. Finally, it has been found that the novel triazolylmetal salts of the general formula I are distinguished by a particularly high activity as fungicides.

The triazole derivatives of general formula II used as starting material are known, and / or can be prepared by generally known methods and methods. As examples of the compounds of general formula II, the following may be mentioned:

χ n Q 4-C! 1 CO 2,4-Cl ₂ 2 CO - 0 CO 4-Br 1 CO 4-P 1 co 2-Cl, 4-Br 2 co 3-CI 1 CH (OH) 2,4,6 Cl ₃ 3 CO 4-NH ₂ 1 CO 2,3- (CH ₃ I ₂ 2 CO 4-No ₂ 1 CO 4-CH ₃ O- 1 CH (OH) 4-C ₆ H ₆ - 1 CO -SO ₂ 4-C ₆ H ₅ -CO- 1 CO 4-CF ₃ O- 1 CO

The metal salts of the general formula III used as a further starting material are likewise known. In the formula III Me metals from the II. And IV. Main group, and la, Ma and IVa-VIIIa mean secondary group of the periodic system, which tend to form complexes. Me means in particular copper, zinc, manganese, tin or magnesium. As the acid moiety, these metal salts may contain benzoic acid and its substituted derivatives. These salts are known and are readily available by reacting corresponding inorganic metal salts with alkali metal salts of the aromatic carboxylic acid.

Suitable diluents for the process according to the invention are water and inert organic solvents. These include, in particular, alcohols, such as methanol and ethanol, ketones, such as acetone, ethers, such as diethyl ether, dioxane or tetrahydrofuran.

The reaction temperature can be varied widely, without affecting the amount and quality of the final product. It is generally between 5-5O ⁰ C, in particular 20-25 ° C worked.

To carry out the process according to the invention, the starting materials are used in equimolar amounts. For this purpose, the oxidation number of the metal ion in metal salts of the general formula III is to be considered. An excess of one or the other reaction component brings no significant advantages. The fungicidal active compounds can be isolated by the methods customary in organic chemistry.

The new triazolyl metal complexes of the general formula I show a particularly high activity and a broad spectrum of activity. The active compounds according to the invention can be used on their own or in a mixture with other active ingredients to combat phytopathogenic fungi of the genera Phycomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes of the order Eumyertina. The new active ingredients show a contact, protec- tive, preventive and systemic, curative or erotic effect. The new agents absorb through the roots and leaves, and can be used in a wide area z. B. be used by seed treatment, soil treatment and spraying. As spraying agents, the new active ingredients can also be used successfully after infection.

Particularly effective are the new active ingredients against mildew fungi, such as Erysiphales from the genus Ascomycetes. They can be used to control Sphaerotheca fuliginea and Erysiphe cichoracearum in cucumbers, from Rodosphaera lencotricha in apples, from Erysiphe graminis f. sp. tritici and f. sp. Hordei in wheat and barley, Inicinula necator in grapes, and Levsillula tanrica in paprika and tomatoes. It is also possible to control rust fungi, such as Basidiomycetes of the genus Kredinales, in particular Pucciniaceae in various cereals, such as Puccinia graminis, Puccinia strioformis, Puccinia recondita.

The new active ingredients prevent the multiplication of certain pests and bacteria.

The active compounds according to the invention can be flushed out in the form of spraying agent in an amount of 12.5-150 μg of active ingredient / ha, or in a concentration of 1-5000 mg of active ingredient per liter in the field or in the air. Their application is not complicated by any unpleasant odor or skin irritation. The low levels of use reduce the pesticide load on nature.

The active compounds according to the invention show no phytotoxicity on crop plants.

In order to broaden the spectrum of action, or to increase the effectiveness, the active compounds according to the invention can be mixed with other fungicides, further acaricides and with growth regulators. These combinations can be used in the form of tank mixes, but their mixing is also possible in the formulation.

The active compounds can be converted into the customary formulations, such as solutions, emulsions, suspensions, pastes and granules. These formulations are prepared in a known manner, e.g. by mixing the active compounds with extenders, as z. For example, liquid solvents and / or solid carriers, optionally with the use of surfactants, emulsifiers and / or dispersants and / or Schauberzeugenden agents, as well as their usual formulation auxiliaries. In the case of using water as an extender z. As well as organic solvents can be used as auxiliary solvent. Suitable liquid solvents besides water are:

aromatic hydrocarbons, such as benzene, toluene, xylene, or alkylnaphthalenes, chlorinated aromatic or aliphatic hydrocarbons, such as chlorobenzenes, methylene chloride, and petroleum fractions, alcohols, such as butanol or glycol, and their ethers and esters, ketones, such as acetones, methyl ethyl ketone , Methyl isobutyl ketone, or cyclohexanone, strong polar solvents such as dimethylsulfoxide, dimethylformamide. Suitable solid carriers are: natural or synthetic minerals, such as kaolins, montmorillonite, talc, quartz, attapulgite, diatomaceous earth and highly dispersed silicic acid, alumina and synthetic silicates. Suitable emulsifiers and / or foam formers and / or other formulation auxiliaries are: nonionic, anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, alkyl sulfates, alkyl sulfonates, aryl sulfonates, and protein hydrolysates, furthermore as dispersants, liquor liquors, methyl cellulose and lignite.

The formulations generally contain between 0.1 and 95 wt .-% of active ingredient, preferably between 1 and

The active compounds may be present in themselves or in admixture with other active substances, such as fungicides, insecticides, acaricides, nematicides, herbicides, wild deterrents, growth regulators, artificial fertilizers or soil conditioners, in their formulations and in the forms of use prepared therefor, such as solutions, emulsions, Suspensions, pastes or granules are used. The use is done in the known manner, such as. B. by spraying or seed treatment.

When used as foliar fungicides, the active ingredient concentration of the use forms may weigh from 0.0001 to 0.1% by weight of active ingredient, preferably from 0.001 to 0.05% by weight of active ingredient.

The new active ingredients continue to show as the other triazole derivatives also a microbicidal and growth-regulating effect.

embodiment

The invention will be explained in more detail with reference to the following examples.

example 1

Bis- [1- (1,2,4-triazol-1-yl) -1- (4-chlorophenoxy) -3,3-dimethylbuthan-2-one] -copper-3,5- (dinitrobenzoate) To a solution of 24.3 g (0.05 mol) of copper (II) - (3,5-dinitrobenzoate) in 150 ml of tetrahydrofuran is added dropwise with stirring, a solution voη 29.4g (0.1 mol) 1- (1,2, 4-triazol-1-yl-1) - (4-chlorophenoxy) -3,3-dimethylbutan-2-one in 100 ml of tetrahydrofuran. After completion of the addition, the mixture is stirred for 3 hours at room temperature, then sucks the resulting precipitate and washed with a little tetrahydrofuran. 600 ml of water are added to the filtrate, thereby precipitating further solids. The resulting precipitate is collected and dried.

This gives 51.1 g (95% of theory) of bis-Hd ^^ - triazole-i-yD-iM-chlorophenoxy-SS-dimethylbuthane-1-yl-copper-O-dinitrobenzoate), mp 185 ° -188 ° C.

The 1- (1,2,4-triazol-1-yl) -1- (4-chlorophenoxy) -3,3-dimethylbuthan-2-one used as the starting material is a known compound.

The copper (II) - (3,5-dinitrobenzoate) required as a further starting material is obtained from 21.2 g (0.1 mol) of 3,5-dinitrobenzoic acid by dissolution in a solution of 4.0 g (0.1 mol). Sodium hydroxide prepared in 75 ml of water. After complete dissolution, the copper salt is precipitated with a solution of 8.5 g (0.05 mol) of copper (II) chloride dihydrate in 25 ml of water. The batch is stirred for 10 minutes, and left for one hour. The salt is finally filtered off with suction, washed with water and dried.

Example 2

Bis [1- (1,2,4-triazol-1-yl) -1- (2,4-dichlorophenoxy) -3,3-dimethylbuthan-2-one] copper (II) p-toluenesulfonate 20.3 g (0.05 mol) of copper (II) p-toluenesulfonate in 50 ml of water. A solution of 32.8 g (0.1 mol) of 1- (1,2,4-triazol-1-yl) -1- (2,4-dichlorophenoxy) -3,3-dimethylbuthane is added dropwise to this solution. 2-on in 75ml ethanol with stirring. After completion of the addition, the mixture is stirred for 2 hours, finally sucking the precipitate, washed and dried. 43.6 g (82% of theory) of bis [1- (1,2,4-triazol-1-yl) -1- (2,4-dichlorophenoxy) -3,3-dimethylbuthane-2 are thus obtained -on] -copper (II) p-toluenesulfonate, pour point

Example 3

Bis- [1- (1,2,4-triazol-1-yl) -l- (4-chlorophenoxy) -3,3-dimethylbuthan-2-ol] -copper (II) sulfosalicylate Dissolve 24.9 g ( 0.05 mol) of copper (II) sulfosalicylate in 50 ml of water and mixed with 29.6 g (0.1 mol) of 1- (1,2,4-triazol-1-yl) -1- (4-chlorophenoxy) -3,3-dimethylbuthan-2-ol in 50 ml of ethanol. After stirring for 2 hours, the solvent is distilled off in vacuo, and the residue is recrystallized from ether. 47.4 g (87% of theory) of bis [1- (1,2,4-triazol-1-yl) -1- (4-chlorophenoxy) -3,3-dimethylbuthan-2-ol are thus obtained ] -copper (II) -sulfosalizylat, Melting point: 115-120 ⁰ C.

Example 4

Bis [1- (1,2,4-triazol-1-yl) -1- (4-bromophenoxy) -3,3-dimethylbuthan-2-one] copper (II) - (4-fluorobenzoate) Man 17.1 g (0.05 mol) of copper (II) -4-fluorobenzoate in 80 ml of ethanol, and treated with a solution of 33.8 g (0.1 mol) of 1- (1,2,4-triazole-1 -yl) -1- (4-bromophenoxy) -3,3-dimethylbutan-2-one in 150 ml of ethanol. The mixture is stirred for 4 hours, filtered off with suction, washed and dried. Thus, 49.9 g of bis [1- (1,2,4-triazol-1-yl) -1- (4-bromophenoxy) -3,3-dimethylbuthan-2-one] copper (II) - ( 4-fluorobenzoate), pour point: 194-197 ° C.

Analogously, the following compounds of general formula I can be prepared:

Example no. me X η Q k y ¹ y ² m 1 Pour point ⁰ C 5 Cu 4-CI 1 CO 2 2,4-Cl H 2 2 131-132 6 Cu 4-CI 1 CO 2 3,5-NO ₂ H 2 2 185-188 7 Cu 4-CI 1 CO 2 3-NO ₂ 4-CI 1 2 185-190 8th Cu 4-CI 1 CO 2 H 2-OH 0 2 9 Cu 4-CI 1 CO 2 2-C ₃ H ₇ H 1 2 130-135 OCO 10 Cu 4-CI 1 CO 2 2-CI H 1 2 11 Cu 4-CI 1 CO 2 4-CI H 1 2 12 mg 4-CI 1 CO 1 2,4-Cl H 2 2 13 sn 2,4-Cl 2 CO 2 2,4-Cl

me X η Q k y ¹ y ² m 1 -5- 251277 Example no. Mn 4-CI 1 CO 1 4-CI H 1 1 Pour point ⁰ C 14 H 4-CI 1 CO 2 3,5-NO ₂ 4-CI 2 2 15 N / A 4-BI 1 CO 2 3,5-NO ₂ 4-CI 2 2 16 Mn 4-BI 1 C (OH) H 3 4-CI H 1 2 17 Zn 2,4-Cl 2 CO 2 2-CI H 1 2 18 Cu 4-CI 1 CO 2 4-P H 1 2 19 Cu O C (OH) H 4 2-CI H 1 2 194-197 20

Example 21

Dispersible powder with 25% active ingredient content Composition: 25% active ingredient according to Example 5, 5% finely divided silica, 6% lignosulfonate, 1% alkylnaphthalenesulfonate and 63% kaolin.

Example 22

Dispersible powder with 50% active ingredient content Composition: 50% active ingredient according to Example 1.10% highly dispersed silicic acid, 6% lignosulfonate, 2% fatty acid methyllauride and 32% diatomaceous earth.

Example 23

Porridge with 25% active ingredient content Composition: 25% active ingredient according to Example 16.10% lignosulfonate, 1% alkyl naphthylsulfonate, 0.5% dye and 63.5% kaolin.

Example 24

Suspension with 10% active ingredient content Composition: 10% active ingredient according to Example 14.5% lignosulfonate, 0.5% dye and 84.5% kazeinate solution.

Example 25

Porridge with 20% active ingredient content Composition: 20% active ingredient according to Example 8.0.5% dye, 10.0% isopropyl alcohol and 69.5% dimethyl sulfoxide.

Example 26

Emulsifiable concentrate with 10% active ingredient content Composition: 10% active ingredient according to Example 12.5% non-ionic organic sulfonate, 5% orthophosphoric mono / di (- (oxy-ethyl-aryl) -ester, 40% N-methyl-2- pyrrolidone, 40% xylene.

Example 27

Powder with 25% active ingredient content Composition: 25% active ingredient according to example 20.2% dye, 3% purified mineral oil and 70% kaolin.

Example 28

Dusting agent with 1% active ingredient content Composition: 1% active ingredient according to Example 13.10% kaolin and89% talc.

Example 29

Suspension concentrate with 40% active ingredient content Composition: 40% active ingredient according to Example 6.3% N-alkyl-naphthylsulfonate-formaldehyde condensate, 4% mixture of anionic and non-ionic surfactants, 1% foaming agent, 0.1% anionic polysaccharides 5 , 0% ethylene glycol and 46.9% water.

Example 30

Oily suspension concentrate with 25% active ingredient content Composition: 25% active ingredient according to Example 5.6 ^V .S fatty alcohol polyäthylenglykoläther, 34% water and 35% paraffin oil.

Example 31

Control of wheat powdery mildew Sow "Mv-4" wheat in the usual soil mixture in a pot, grow at least 10 plants per pot and treat the plants after reaching the 2 leaves, 4-6 leaf stage if desired.

From a formulation according to Example 21, a spray liquor is prepared. With conventional spray pots (eg the type of tea jet TG or TK), arranged on a frame according to the usual Schrifteldspritzrahmen, the plants are sprayed with the preparation with certain active ingredient content. 24 hours after treatment, the plants are vaccinated with wheat powdery mildew (Erysiphegraminis tritici). Place the pots with 5-7 parallel in the glasshouse with 20 ⁰ C temperature.

The infestation is assessed 12-14 days after the treatment according to Hinfner (Hinfner, K. and Bekesi, P .: Orszagos Fajtakiserletek [field variety trials] 113,1971, Budapest).

The active ingredients, the concentration and the results are given in Table I.

Table I Combat% 0.5, ug / ml 10 / xg / ml 60 Combat Erysiphegraminisf. tritici 74 29 active substance 52 97 83 81 Example 16 78 90 Example 7 76 82 Example 5 80 Example 10 Example 11 Active substance V (known)

Example 32

Systemic action against wheat powdery mildew

To investigate the systemic effect, the soil of plants, grown as described in Example 31, is watered with an active ingredient preparation. The active ingredient concentration of the preparation is given based on the volume of the soil unit.

The basting is carried out according to the requirements of the plants.

The active ingredients, the concentration and the results are given in Table II.

Table II

Systemic action against wheat powdery mildew active infestation in%

2.50 / g / ml 1.25 ^ g / ml 0.625 //, g / ml *

Example 6 5.3 ± 3.9 from *** 10.5 ± 3.5 to 15.0.0 ± 2.2d

Compound V (known) 2.3 ± 1.7 a 4.5 ± 3.3 from 8.3 ± 4.1 abcd

Compound VI 26.2 ± 5.7e 36.5 ± 7.6f 33.8 ± 7.3f

(known**)

Control 56.8 ± 8.4

SzD _5% 6.82

* Concentration in ^ g of active ingredient per ml of soil volume ** 10-fold concentration (2,50,12,5 and 6,25μ9 / ιτιΙ)

*** Duncan test (Duncan Multiple Range Test) i. the data with the same letters show no differences with P = 95% probability.

Example 33

Kuretive action against wheat powdery mildew

To test the curative effect is carried out analogously as described in Example 31, but with the difference that the plants are treated with the preparation of active compound 2 days after vaccination. Infestation is assessed 14 days after vaccination.

The active ingredients, the concentration and the results are given in Table III.

Table III ·

Kuretive effect

Active ingredient infestation in%

Drug concentration in μg / ml

50 25 12,512.5

Example 6 5.3 ± 1.3a 10.3 ± 1,7ab 22.3 ± 5.0 d Connection V (known) 13.8 ± 5.7 bed 18.8 ± 1.5 cd 19.0 ± 3.4 cd Connection Vl 50.3 ± 5.2 e 54.0 ± 8.5 e 50.8 ± 2.5 e (known*) control 51.0 ± 3.4 e SzD ₅ % 7.29

*: 10-fold concentration (500, 2.50 and 125 / xg / ml).

Example 34

Effect against cucumber mildew

Cucumbers of the type Kecskemeti bötermö (Kecskemeter Bruch rich) are sown in garden soil mixture in growing pots. 2 plants per pot are allowed to grow to 4 leaves of stage, if desired until 6 leaves of the stage. The plants are sprayed with the active ingredient in the form of spray mixture by means of spray gun to drip wet. After 24 hours, the plants are sprouted with spore suspension of cucumber powdery mildew (Sphearothecafuiginea) (10 ⁵ spores per ml). Place the pots in the glasshouse at 24 ⁰ C temperature. The infestation is after 14 days after Spencer (Crop Protection Agents-Their Biological Evaluation, ed:

N. R. McFarlene, Academic Press, pp 455,1977).

The active ingredient, the concentration and the results are given in Table IV.

Table IV

Systemic effect on cucumbers

Active ingredient infestation in%

Drug concentration in / xg / ml 50

12.5

Examples 4.5 ± 2.4 a 14.0 ± 7.0 bed 22,0 ± 6,0 de Connection V (known) 11.0 ± 7,6ab 12.5 ± 3.7 abc 22.3 ± 4.4 de Connection Vl 60.5 ± 3.3 f 58.0 ± 9.3 f 53.5 ± 3.4 f (known*) control 88.0 ± 1.6 SzD _5% 8.09

*: 10-fold concentration (500, 250 and 125 mg / ml).

Example 35

Systemic action against cucumber mildew by soil treatment

The systemic effect by soil treatment is carried out analogously as described in Example 32. The results

are given in Table V.

Table V

Soil treatment of cucumbers active ingredient infestation in%

Drug concentration in / ng / ml

2.50 1.25 0.625

Examples 3.8 ± 3.3 from 15.3 ± 8.1 ede 22.3 ± 4.3 ef Connection V (known) 0.0 ± 0.0 a 2.5 ± 3.3 from 18.5 ± 8.7 de Connection Vl 76.8 ± 3.8 gh 71.0 ± 6.5 g 74.8 ± 5.7 g (known*) control 84.0 ± 4.2 SzD _5% 7.72

*: 10-fold concentration (25,0,12,5 and 6,25Mg / ml).

Example 36

Control of barley powdery mildew

One sows barley of the type Viktoria in usual soil mixture in Gewaupöpfen. Leave at least 10 plants per pot

grow to 4-6 leaves stage.

Furthermore, the procedure is analogous to that described in Example 31.

The results are given in Table VI.

Table VI

Contacts Action against barley mildew active ingredient infestation in%

Drug concentration in μg / ml

50 25 12.5

Example 6 5.0 ± 2.0 a 6.0 ± 2.0 a 11.7 ± 3.2 a Connection V (known) 8.7 ± 1.5 a 8.3 ± 3.3 a 13.0 ± 1.0A Connection Vl 23.3 ± 13.3 b 27.3 ± 4.7 b 27.7 ± 2.1 b (known*) control 56.7 ± 2.3 SzD ₅ = / ,, 6.91

*: 10-fold concentration (500.250 and 125 / ig / ml).

Example 37

Soil treatment against barley powdery mildew

The results obtained by soil treatment are given in Table VII.

Table VII

Soil treatment of barley

Active ingredient infestation in%

Concentration of active ingredient //, g / ml 2.50 1.25

0.625

Example 6 3.3 ± 2.3 ab

Compound V (known) 0.7 ± 0.6 a

Connection Vl 25.7 ± 3.1 d (known *)

10.3 ± 5.9bc 2.3 ± 1.5 from 23.7 ± 9.1 a

9.3 ± 2.1 be 9.3 ± 2.1 be 22.0 ± 4.6 d

Continuation of Table VII

Active ingredient infestation in%

Active substance concentration in μg / ml

2.50 1.25 0.625

Control 51.0 ± 8.2

SzD _5% 7.06

*: 10-fold concentration (25.0, 12.5 and 6.25 mg / ml).

Example 38

Fighting wheat powdery mildew in free field One sows autumn wheat of the type Mv-4 at free field with the usual agrotechnical methods. At the end of autumn or early winter the field is covered with wheat powdery mildew (Erysiphe graminis s tritici). In the spring, 3.5 χ 4m plots are determined in the unoccupied interior parts of the field, with a control plot without treatment adjacent to each plot. The parcels are treated with the usual plant protection technologies.

The infestation is evaluated after 21 days after the last treatment to Hinfner.

The active ingredients, the concentration and the results are given in Table VIII.

Table VIII

Free field trials

Active ingredient infestation in%

Concentration of active ingredient in kg / ha 0 £ 5 0.375

Example 6 24.00 (1.41) a 31.50 (3.54) from

Examples 36.50 (6.36) abc 46.00 (4.24) cd

Compound V (known) 33.50 (3.54) abc 46.00 (4.24) cd

Control 60.00 (1.41) d

The advantages of the invention can be summarized as follows:

The invention makes it possible to reduce the application rate of the thiazole compound, which is of great importance for environmental protection.

- From an economic point of view, the smaller price of the active ingredients can be taken into account.

The active compounds according to the invention are readily available and usable.

Claims (1)

Invention claim: 1. Fungicidal agent, characterized by a content of at least one triazolyl-metal complex of the general formula I. me CH. - O-CH-Q-C-CH.