CS199531B2 - Fungicide and process for preparing effective compounds - Google Patents

Abstract

1. 1-(2-Phenylethyl)-triazolium salts of the general formula see diagramm : EP0000017,P19,F1 in which R represents halogen, alkyl with 1 to 4 carbon atoms and phenyl or phenoxy optionally substituted by halogen, n represents integers from 0 to 3, R**1 represents the group -O-R**2 , alkylmercapto or alkylcarbonyloxy with in each case 1 to 4 carbon atoms in the alkyl part, R**2 represents alkenyl with 2 to 4 carbon atoms and benzyl optionally substituted by halogen, R**3 represents alkyl with 1 to 6 carbon atoms, pinacolyl and benzyl or benzoylmethyl optionally substituted by halogen and Z represents halogen.

Description

The invention relates to novel 1- (2-phenylethyl) triazole salts, to a process for their preparation and to their use as fungicides.

It is already known that 1- [β-aryl- [8- (R-oxy) ethyl] imidazoles, such as 1- [β-butoxy- N - (4'-chlorophenyl) ethyl] imidazole, and 1- [ (3-Aryl- [3- (R-oxy) ethyl] triazoles, such as

1- (R-allyloxy- [3- (4'-chlorophenyl) ethyl] -1,2,4-triazole) exhibit good fungicidal activity (see DOS Nos. 2063 857 and 2,640,823). however, it has been known for some time that zinc ethylene-1,2-bis-dithiocarbamate is a good means of combating fungal diseases in plants [cf. Phytopathology 33, 1113 (1963)] However, the use of this substance as a seed dressing is only possible to a limited extent, since the compound is poorly effective when applied at lower levels and concentrations.

It has now been found that the novel 1- (2-phenyl-ethyl) -triazolium salts of the general formula I in which

R is chlorine, phenoxy or chlorophenoxy, n is 1 or 2,

R ^{* 1 * * *} represents an oxybenzyl group, optionally substituted with 1 to 3 chlorine atoms, an allyloxy group, an acetoxy group or a tert-butylcarbonyloxy group,

R ⁵ represents a methyl group, an optionally substituted benzoyl group, which may itself be substituted by 1 to 3 chlorine atoms, or a tert-butylcarbonyl group, or a dichlorobenzyl group, and

Z represents a halogen atom, they have potent fungicidal properties.

Furthermore, it has been found that the 1- (2-phenylethyl) triazolium salts of the above general formula (I) are obtained by substituting 1-phenyl-2-thiazolyl-ethyl derivatives of the general formula (II)

wherein R, R ¹ and ⁿ are as defined above, reacted with halides of formula III

R 5 -X, (III) wherein.

R ⁵ is as defined above, and

X represents a halogen atom, in the presence of a diluent.

In many cases, it has proven advantageous to use the corresponding reactive ester obtained by reacting the corresponding alcohol with the appropriate acid instead of the halide of formula III.

Surprisingly, the 1- (2-phenylethyl) triazolium salts of the invention exhibit considerably higher

How. As is apparent from the nuclear resonance data, in this reaction the alkyl moiety preferably binds to the nitrogen atom at the 4-position of the 1,2,4-triazol-1-yl moiety. However, depending on the reactivity of the alkyl halide and the starting material of formula (II), 1 can be alkylated at the nitrogen atom at the 1-position 1,2, -

Of a 4-triazol-1-yl residue. Both of these types of alkyl group linkages as well as mixtures resulting from the aforementioned alkylation are within the scope of the invention.

Some of the starting materials of formula (II) are known (cf. DOS No. 25 47 953 and DOS No. 26 40 823). The hitherto unknown starting materials of the formula II can be obtained, for example, by one of the following processes:

fungicidal activity, in particular against various types of rust and powdery mildew than the prior art known 1- [β-aryl-β- (R-oxyethyl) imidazoles and -triazoles, for example 1- [β-butoxy] β- (4'-chlorophenyl) ethyl] imldazole, which are related chemically and efficiently, and than zinc ethylene-1,2, -bis-dithiocarbamate, which is a known substance of the same activity. hence the enrichment of the prior art.

If [1- (2,4-dlchlorophenyl) -2- (1,2,4-triazol-1-yl) ethyl] - (2,4 dichlorobenzyl) ether and monochlorpinacoline are used as starting materials, the reaction may proceed according to the invention described by the following reaction scheme:

in which

R and n are as defined above and;

M represents an alkali metal, preferably lithium, sodium or potassium, a quaternary ammonium or phosphonyl group, with a halide of formula V

^Hal-R1 (V)

a) reaction of alkoxides derived from 1-hydroxy-1-phenyl-2-triazolylethane derivatives of the general formula IV in which:

R ¹ has the abovementioned meaning and

Hal represents chlorine or bromine, in the presence of an organic solvent, for example dioxane or chloroform at temperatures between 20 and 120 ° C.

To isolate the resulting product, the reaction mixture was freed from the solvent and the residue was stirred with water and an organic solvent. The organic phase is separated, worked up and purified in the usual manner.

Suitably, starting from a 1-hydroxy-1-phenyl-2-triazolylethane derivative, the latter is converted into an alkali metal alkoxide corresponding to the above general formula (IV) by treatment with an alkali metal hydride or amide in a suitable inert solvent. , which is then reacted immediately without isolation with a halide of the formula (V) to give the compounds of the formula (II) in a single step to form the alkali metal halide.

According to a further preferred embodiment, both the preparation of the alkoxide of the formula IV and the reaction with the halide of the formula V are conveniently carried out in a two-phase system, such as in a mixture of aqueous sodium or potassium hydroxide and toluene or methylene chloride.

phase transfer such as ammonium or phosphonium compounds.

The starting materials of the general formula (II) can also be obtained by:

b) reacting the corresponding 1-hydroxy-1-phenyl-2-triazolylethanes corresponding to the alkoxides of the general formula IV with the corresponding acid anhydrides in a manner known per se, for example in molar amounts, in the presence of an inert organic solvent such as acetone; acid in the presence of an acidic or basic catalyst, for example sodium acetate, at a temperature between 0 and 150 ^° C, after which the compounds of the formula II are isolated in the customary manner.

The 1-hydroxy-1-phenyl-2-triazolylethane derivatives from which the alkoxides of the formula IV are derived are known (see DOS Nos. 24 31 407 and DOS No. 25 47.953).

Examples of the 1-phenyl-2-triazolylethyl derivatives of the general formula (II) used as starting materials in the process according to the invention are the compounds summarized in Tables 1 and 2 below.

TABLE 1

Rn

Melting point (° C) or refractive index

2,4-012 ^<W \ O / ^{CI CI} 84 2,4-012 —CH2 — CH = CH2 n _D ²⁰ = 1.545 Whose 4-C1 78 4-C1 111

Melting point ( ^e C) or refractive index

R ²

4-Cl

2,4-CL ·

2,4-CL ·

Ct

Cl

ct

225 (decomposition). (x ——— NMS)

По ^{22 w} 1.570

200 (X-y-NDS)

213 (x — NDS)

145 (decomposition) (x— | -NDS)

237 (s-NDS) £

124

140 (x HCl)

108

89—91

165

107

103

135

4-0 o

Cl

212 (x-1-NDS) £

Legend: NDS = 1,5-naphthalenedisulfonic acid

212 (x — 1 — NDS) £

203

TABLE -2

•. R ⁿ R4 Melting point (° C) 2,4-012 С (СНз) з 149—151 (xHNOs) 2,4-Cb CHs 92—96 CH3 123 Q- ^ Cl CH3 150 (x HNO3) - (C "C C (CH3) 3 ' 121 4-C1 CH3 90—92 4-C1 C (CH 3) 3 135—136

ethers such as diethyl ether and tetrahydrofuran as well as chlorinated hydrocarbons such as methylene chloride and chloroform.

The reaction temperatures of the process according to the invention can be varied within a wide range. In general, the reaction is carried out at a temperature of between about 0 DEG to 120 DEG C., preferably at a temperature of from -20 DEG to 90 DEG C., optionally under reflux of the solvent used.

When working according to. The starting materials of the formula (III ') are generally known compounds in organic chemistry or can be obtained in a manner known per se.

Suitable diluents for the process according to the invention are preferably polar organic solvents, which preferably include nitriles, such as acetonitrile, sulfoxides such as dimethylsulfoxide, formamides such as dimethylformamide, ketones such as acetone,

199631 are preferably used in molar amounts. The isolation of the compounds of formula (I) is carried out in a conventional manner.

The active compounds according to the invention show a strong fungitoxic effect. The substances at concentrations necessary for combating fungi do not damage crop plants. For these reasons, they are suitable for use as agents for protecting plants against fungal diseases. Fungitoxic agents are used in plant protection to combat fungi in the classes - Plasmodiophoromycetes, Óomycetes, Chytridiomycetes, - Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.

The active compounds according to the invention have a broad spectrum of action and can be used against parasitic fungi attacking the above-ground parts of plants, attacking plants from the soil, as well as agents of fungal diseases transmitted by seed. The active compounds described above have been shown to be particularly effective against parasitic fungi on aerial parts of plants.

As plant protection agents, the active compounds according to the invention can be used with particularly good results in combating Venturia species, such as against the scab of Fusicladium dendriticumj, to combat true powdery mildew, cereal diseases.

Particularly preferred is the partial systemic action of the compounds according to the invention, which makes it possible to protect plants against fungal infestation by the introduction of active substances into the above-ground parts of the plants via soil and roots.

As plant protection agents, the active compounds according to the invention can be used for the treatment of seed or soil and for the treatment of aerial parts of plants.

The active compounds according to the invention can be converted into customary formulations such as solutions, emulsions, suspensions, powders, pastes and granules. These compositions are prepared in a known manner, for example by mixing the active ingredient with fillers, i.e. liquid solvents, liquefied gases under pressure and / or solid carriers, optionally using surfactants, i.e. emulsifiers and / or dispersants, and / or foaming agents. reagents. If water is used as a filler, it is also possible to use organic solvents as auxiliary solvents. Basically suitable liquid solvents are: aromatics such as xylene, toluene, benzene or alkylnaphthalenes; chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, alcohols such as butanol or glycol, and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methylisobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethylsulfoxide, and water. Liquefied gaseous fillers or carriers are. refers to liquids which are gaseous at normal temperature and pressure, for example aerosol propellants such as dichlorodifluoromethane or trichlorofluoromethane. Suitable solid carriers are: natural stone meal, such as kaolins, alumina, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and synthetic stone meal, such as highly disperse silica, alumina and silicates. Suitable emulsifiers are nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene ethers of fatty alcohols, for example alkanol sulfoleglycol ether, alkelsulfonates, alkylsulfate, arylsulfonates, as well as protein hydrolysates, and as dispersants, for example, lignin and methylcellulose waste Louise.

The active compounds according to the invention may be present in the formulations in admixture with other active substances, such as fungicides, insecticides, acaricides, nematicides, herbicides, avian protective agents, growth agents, plant nutrients and soil improvers.

The concentrations according to the invention generally comprise between 0.1 and 95% by weight of active ingredient, preferably between 0.5 and 90% by weight.

The active compounds according to the invention can be applied as such, in the form of concentrates or from further dilution forms prepared therefrom, such as ready-to-use solutions, emulsions, suspensions, powders, pastes and granules. The application is carried out in a conventional manner, for example by dressing, spraying, dusting and tossing, dry pickling. wet, for. wet or in suspension or incrustation.

When the active compounds are used as foliar fungicides, their concentrations in the formulations can be varied within a wide range. These concentrations generally lie between 0.1 and 0.00001% by weight, preferably between 0.05 and 0.0001% by weight.

In the treatment of seed, it is generally necessary to use from 0.001 to 50 g, preferably 0.01 to 10 g, of active compound per kilogram of seed.

For soil treatment; it is necessary to use from 1 to 1000 g for each m ^{3 of} soil, preferably from 10 to 200 g of active substance.

The versatility of the compounds of the invention is illustrated by the following examples.

Example A;

Protective test for apple powdery mildew (Podosphaera)

Solvent: 4.7 parts by weight of acetone

Emulsifier: 0.3 part by weight of alkylaryl polyglycol ether.

Water: 95.0 parts by weight

19'9 5 31

The amount of active ingredient required to achieve the desired concentration of active ingredient in the spray is mixed with said amount of solvent and the concentrate is diluted with the indicated amount of water containing the above ingredients. ...

Young apple seedlings having 4 'to 6 leaves are sprayed until wet. The plants are kept in a greenhouse at 20 ^° C and a relative air humidity of 70% for 24 hours, after which they are inoculated by dusting. spores of the fungus Podosphaera leucotricha. (apple powdery mildew) and placed in a greenhouse with a temperature of 21 to 23 ^° C and a relative air humidity of about · 70 ® / o ·. .......

days after inoculation, the infected seedlings are infected. The values obtained are converted to. % · Attack.

% · Means that · no infection occurred, 100 percent represents · complete infestation of plants.

Active substances, · concentration of active substances, as well as the results obtained, are given in the following table:

TABLE A 'Protective test · for powdery mildew (Podosphaera)

Active substance Infestation · v ·% · at active substance concentration 0,0025%

'; Cl '' / 3 · N _from \ - / | 4 Br® 1 O 1 M)

Active substance

Infestation in '% at active substance concentration 0.0025%

By spraying, young apple seedlings in the 4 to Θ leaf stage are sprayed until wet. The plants are kept for 24 hours in a greenhouse at 20 ° C and 70% relative humidity, then inoculated with an aqueous suspension of spores of Fusicladium dendrltlcum (apple scab) and plated for 18 hours in a humid chamber at 18-20 ° C. and 100% relative humidity. «

The plants are then replanted for 14 days in a greenhouse.

infestation of the seedlings is observed on days after inoculation. The values obtained are converted to infestation in%.

Example 1 a d В

Protective test for apple scab (Fusicladium)

Solvent: 4.7 parts by weight of acetone Emulsifier: 0.3 parts by weight of alkylaryl polyglycol ether

Water: 95 parts by weight

The amount of active ingredient required to achieve the desired concentration of active ingredient in the liquid spray is mixed with the stated amount of solvent and the concentrate is diluted with the specified amount of water containing the above ingredients.

198531

11

O o / o means no attack, 100%. The results and the results are given in the meaning of complete infestation of plants, the following table:

Active substances, concentration of active substancesTABLE В

Protective test for apple scab (Fusicladium)

Active substance Infestation in% at active substance concentration 0,0025% a

CH-CH-1

I ^Z

O

Cfy * 1/2 'IQ

H j (ZOUM,}

7'4 ·

Example C (shoots treatment) on Eryvar. hordei (mycosis destroying the forged concentrate is then diluted with water to the desired final concentration).

To determine the protective effect, young barley plants (Amsel species) in the single leaf stage are sprayed to the moistening with the active ingredient prepared and, after drying, dusted with spores of Erysiphe graminis var. hordei.

After six days, when the plants are grown at 21 to 22 ^e C and 80-90% atmospheric humidity, the extent of disease was evaluated on plants. The degree of attack is expressed in

Protective test (siphe graminis leaves)

To prepare a suitable active ingredient, 0.25 part by weight of the active compound is stirred in 25 parts by weight of dimethylformamide and 0.06 part by weight of alkylaryl polyglycol ether as emulsifier and 975 parts by weight of water are added. Gets199931 v

percent infection of untreated control plants, with 0% indicating no infestation and 100% the same infestation as untreated control plants. The testing ¹⁹ on ^the more active the compound, the lower the degree of mildew infection.

The following table shows the active substances, the concentration of the active substances in the spray and the extent of the disease:

TABLE C

Protective test (shoot treatment) for Erysiphe graminls var. hordei

Active ingredient Concentration effective Infestation in% spray attack of untreated (wt%) control plants untreated

l

CHg-NHCS ^ I Za ch-iwcs' II S, (zfZAtTiA)

Whose

0,025

0,025

100 ALIGN!

25.0

B® ť

O, C, 025

16.3

42.5

0,0 к

No.

Active substance

Concentration of active substance in spraying (% by weight)

Infestation in% attack of untreated * control plants

0,025

0,025

0.0

Example D

Test of systemic action on powdery mildew (Eryšiphe gramlňts var. Hordel) - fungal disease of shoots

The active ingredient is used in the form of powdered seed dressings. This mordant is prepared by mixing the respective active ingredient with a mixture of equal parts by weight of talc and diatomaceous earth to form a finely powdered mixture containing the active ingredient in the desired concentration.

The barley seed is treated by shaking with prepared mordant in a closed glass container. The seed is then sown (3 x 12 grains) 2 cm deep into pots containing a mixture of one volume of standard peat soil and one volume of quartz sand? Germination and emergence of plants

0.025 12.5 takes place under favorable conditions in the greenhouse. 7 days of sowing, when barley plants unfold their first leaf, they are dusted with fresh spores of Eryslphe graminis var. hordei and further cultured at 21-22 ° C and 80-90% relative humidity under 16 hour illumination per day. Typical powdery mildew spots are formed on the leaves of the plants within 6 days.

The degree of infestation is expressed as the percentage of infestation of untreated control plants, with 0% indicating no infestation and 100% the same infestation as untreated control plants. The more active the active substance, the lower the extent of the disease.

The active substances, the active substance concentrations in the mordants, the mordant consumption and the percentage of disease content are as follows:

TABLE D

Systemic effect test on powdery mildew Erysiphe gaminis var. hordei

Active substance Concentration Consumption % Attack active substance mordants' attack in the stain in g / kg '  untreated (wt%) seed control plants

100 ALIGN!

100 ALIGN!

- * 'not infested

With CHf-NHCS. I CH * NHCS (sounds *)

(8)

CH 2 CH-CH

18.3

Example E

Test of effect on mycelium growth

Nutrient medium used:

20 parts by weight of agar-agar

200 parts by weight of potato broth parts by weight, malt parts by weight of dextrose, 5 parts by weight of pepton, parts by weight of secondary sodium phosphate ·

0.3 parts by weight of 'calcium nitrate' · ratio of 'solvent' mixture to 'broth:

parts by weight of solvent

100 parts by weight of agar broth · composition of solvent mixture:

0.19 parts by weight of dimethylformamide

0.01 part by weight of alkyl aryl polyglycol ether as emulsifier

1.80 parts by weight of water are thoroughly mixed with the liquid broth cooled to 42 DEG C. and the mixture is poured into 9 cm diameter Petri dishes. Control plates are also prepared without admixture of the active preparation.

After the broth has cooled and solidified, the plates are inoculated with each of the fungi listed in the following table and incubated at about 21 ° C.

Evaluation is performed on the basis of the fungal growth rate after 4 to 10 days. The evaluation compares the radial growth of the mycelium on the treated broths with that on the control broths. Mushroom growth is assessed using the following 'scale': no fungal growth.

up to 3 very strong growth suppression · up to 5 moderate growth inhibition.

to. 7 slight growth retardation growth 'same as untreated' control boards ..

The active compounds, the active compound concentrations and the results obtained are shown in the following table

The trial fungi are indicated in the table by Roman numbers' with the following meanings:

The amount of active ingredient required to achieve the desired concentration of active ingredient in the broth is mixed with said amount of solvent mixture. The concentrate is

I = »CoUetotrichum coffeanum

II = Vertlcillium _ alboatrum

III = Helminthosporium gramineum

IV = Phytopthora cactorum

Experimental mushrooms

198531

TABLE E

Test for mycelium growth (active substance concentration 10 ppm) Active substance (<S)

(Mark. Та.)

The preparation of the active compounds according to the invention is illustrated by the following non-limiting examples.

Example 1

Cl .........

Preparation of the starting material

Ct

C-ZO 2 -CH-CH 2 N

20.7 g (0.05 mol) [1- (2,4-dichlorophenyl) -2- (1,2,4-triazol-1-yl) ethyl] - (2,4-dichlorobenzyl) of ether and 6.7 g (0.05 mol) of monochloropinacoline in refluxing acetonitrile (50 ml) was heated at reflux for 12 hours. After cooling, the precipitated solid product is filtered off with suction and dried after washing with acetone. 10.9 g (40% of theory) of 1- (2- (2,4-dichlorobenzyloxy) -2- (2,4-dichlorophenyl) ethyl) -tert-butylcarbonylmethyl-1,2,4- m.p. 216-218 ^° C.

. CH

Dissolve 25.8 g (0.1 mol) of 1-hydroxy-1- (2,4-dichlorophenyl) -2- (1,2,4-triazol-1-yl) ethane in 125 ml of dioxane and stirring was added dropwise to a mixture of 4 g of 80% sodium hydride and 100 ml of dioxane. The resulting mixture was heated under reflux for 1 hour. After cooling, the sodium salt thus obtained was added dropwise at room temperature to 20 g (0.1 mol) of 2,4-dichlorobenzyl chloride. The reaction mixture is refluxed for several hours and after cooling the solvent is distilled off. Methylene chloride and water were added to the residue, the organic phase was separated and, after drying with sodium sulfate, evaporated. . Recrystallization of the solid residue of ligroin gave 29 g (70%) of theory [1- (2,4 _; dichlorophenyl) -2- (1,2,4-triazol-1-yl) ethyl] - (2,4 -dichlorobenzyl) ether at melting point · 84 = C.

. 7 шш

Whose

...... Он .....

25.6 g (0.1 mol) of ω- (1,2,4-triazol-1H-yl) -2,4-dichloroacetophenone are dissolved in. 300 ml methanol and the solution at 5-10 ^'C. with stirring are added portionwise 4 g (0.1 mol) of sodium borohydride. The reaction mixture is stirred at room temperature for 1 hour, then boiled for 1 hour, the solvent is distilled off and the residue is briefly heated with 200 ml of water and 40 ml of concentrated hydrochloric acid. _Po basify the reaction mixture with sodium hydroxide can be solid "reaction product 'filter. Mon. Recrystallization from isopropanol and ligroin gave 21.3 g (82 o / ₀ yield) of l-hydroxy-l- (2,4-dichlorophenyl) -2- [l, 2,4-triazol -.- yl) ethane of mp 90 = C.

Cl

269 g (1 mol) of n-bromo-2,4-dichloroacetophenone are dissolved in 250 ml of acetonitrile and this solution is added dropwise to a suspension of 69 g of 1,2,4-triazole and 150 g of potassium carbonate. in 2 liters of acetone-tril boiling under reflux. After heating for 20 hours. The cooled suspension is filtered from the filtrate. the solvent was evaporated and the residue was taken up in ethyl acetate. The solution was washed. . water, dried over sodium sulfate and the solvent was distilled off. The ethyl acetate distillation residue crystallized upon addition of isopropanol. Mon. recrystallization from a mixture of ligroin 'and isopropanol is obtained. 154 g. (60% of theory) of ω- (1,2,4-triazol-1-yl) -1,4-dichloroacetophenone, m.p. 117 ° C. '

Example 2

20.7 g (0.05 mol). Of 1- (2,4-dichlorophenyl) -2- (1,2,4-cyclo-14-yl) ethyl) - (2,6-dichloro-benzyl) ether and 13.4. g (0.05 mol) of 2,4-dichlorobenzoylmethyl ethyl bromide in 250 ml of chloroform (15). hour-in '' boiling under reflux. Reaction mixture. The mixture was allowed to cool, the solvent was distilled off in vacuo and the residue was boiled briefly. acetone. After cooling, the crystalline residue is suctioned off and washed. acetone and dried. 5.6 g (16.5 of theory) of 1- (2- (2,6-dichloro-benzyloxy) -1- (2,4-dichloro-phenyl) -ethyl) -1,4-dichloro-benzoyl-phenyl-1,2,4- triazolium bromide, m.p. 202 cq.

Example 3

20.7 g: (0.05 mol) of [1- (2,4-chlorophenyl) -2- (1,2,4-triazol-1-yl) ethyl) - (2,6-dichlorobenzyl) ether and Methyl iodide (7.1 g, 0.05 mol) in acetonitrile (100 ml) was refluxed for 12 hours. cooler. The reaction mixture is allowed to cool, precipitated. solid material. sucked off, 'and. it is dried after washing with acetone.

26.7 g (96.7% of theory) of l- [2 '(.2,2-di-chlorobenzylpxy) -2- (2,4-nitro-phenyl) ethyl] are obtained?

methyl 1,2,4-triazolium iodide melting at 228-230 ° C with decomposition.

Analogous. .from the way. will also prepare the compounds in the other examples summarized in the following Table 4:

TABLE 4

AND

111331

TI

Claims (2)

A fungicidal composition, characterized in that it contains at least one 1- (2-phenylethyl) triazolium salt of the general formula I as active substance. R '' = (I) in which R is chlorine, phenoxy or chlorophenoxy, n is 1 or 2, R ¹ represents an oxybenzyl group optionally substituted with 1 to 3 chlorine atoms, an allyloxy group, an acetoxy group or a tert-butylcarbonyloxy group, R ⁵ represents a methyl group, an optionally substituted benzoyl group, which itself may be substituted by 1 to 3 chlorine atoms, or a tert-butylcarbonyl group, or a dichlorobenzyl group, and Z represents a halogen atom. 2. A process according to claim 1, characterized in that 1-phenyl-2-triazolylethyl derivatives of the general formula II n. R ¹ - () in which R, R ¹ and n are as defined above, reacted with halides of formula III R ⁵ —X .. ....... (И1) in which R ⁵ is as defined above and X represents a halogen atom, in the presence of a reagent.