CS214711B2 - Fungicide means - Google Patents

Abstract

1. Fungicidal agents, characterized in that they contain at least one hydroxyalkyltriazole of the general formula see diagramm : EP0019189,P14,F1 in which Az represents 1,2,4-triazol-1-yl or 1,2,4-triazol-4-yl, R represents phenyl, naphthyl or tetrahydronaphthyl optionally substituted by halogen and/or alkyl with 1 to 4 carbon atoms, R**1 represents phenyl, cyclopentyl or cyclohexyl optionally substituted by halogen, alkyl and/or alkenyl with in each case up to 4 carbon atoms and R**2 represents hydrogen or R**1 and R**2 together, in the o-position relative to one another, represent a methylene bridge with 3 to 5 methylene groups, R**3 represents halogen, n represents 0, 1, 2 or 3 and m represents 0 or 1, or physiologically acceptable acid addition salts thereof.

Description

The present invention relates to a fungicidal composition comprising as an active ingredient a hydroxyalkyltriazole derivative.

It is already known that 1-phenyl-2-triazolyl-1-ethanols which are substituted in the phenyl moiety have good fungicidal properties (cf. DOS 2 43; 1 407). However, their effectiveness is not always sufficient, especially at low application rates and concentrations.

It has now been found that the hydroxyalkyl triazoles of the general formula I wherein

Az is triazolyl,

R is optionally one or more halogen-substituted phenyl groups,

R 1 is an optionally substituted one or more halogen-substituted phenyl group, m is 0 or 1, and their physiologically tolerable acid addition salts have good fungicidal properties and can therefore be used as active ingredients of fungicidal compositions.

Surprisingly, the hydroxyalkyltriazoles of formula I useful in the present invention exhibit better fungicidal activity than the known prior art 1-phenyl-2-trlazolyl-1-ethanols, which are the closest chemical and effect related compounds. The substances useful in the present invention thus represent a valuable enrichment of the state of the art.

Among the hydroxyalkyl triazoles of formula I useful in the invention, those in which

Az is 1,2,4-triazol-1-yl or 1,2,4-triazol-4-yl;

R represents a phenyl group which is optionally substituted one or more times with halogen, in particular fluorine, chlorine and bromine,

R 1 represents an optionally substituted phenyl group which is halogen substituted one or more times, in particular fluorine, chlorine or bromine being suitable as halogens, m being 0 or 1.

Very particularly preferred are those compounds of formula (I) wherein:

As defined above,

R represents a phenyl group optionally substituted one or two times with chlorine or fluorine, which substituents may be the same or different,

· R ¹ represents a phenyl group which is optionally mono- or disubstituted by chlorine, bromine or fluorine, m is an integer · 0 or 1.

In addition to the compounds of the Examples, the following compounds of formula I may be mentioned individually, wherein Az is 1,2,4- or 1,3,4-thiazolyl-ethyl.

R ¹ OH CH _t Az U> R Ri R - M) -C-ICH _L> = OH. 1 Az (1) m ct - ^ - Ct 0 - © ⁴ - <£) 0 ct O

R1

ϋ active substances and their addition salts. with acids according to the invention have not yet. described. These.' substances. However, their manufacture is described in. DOS 28 51 086 and DOS 28 51 116. byrábět podle. The procedures outlined there are by

a) - triazolylmethylphenyl ketones of the general formula II in which:

R and m are as defined above and

X is halogen, in particular chlorine or bromine, in the presence of a solvent of a conventional Grignard reaction, preferably ether, at temperatures between about 30-80 ° C, or

b) 1-haloalkyl alcohols of the general formula

IV

C-CH3Az (ii) in which:

Az - and R1 are as defined above, in reaction with the Grigard compound of formula III in which:

R- (GH2) _{m and} -Mg-X (III),

R 1 and R 1 -a-m are as defined above and

Y represents halogen, in particular chlorine or bromine, in reaction with triazole, optionally in the presence of an acid binding agent, such as an excess of triazole, and optionally in the presence of an inert organic solvent such as acetonitrile, at temperatures between 30 to 200 ° C, preferably at the boiling point of the solvent. In many cases, it has proven advantageous to use triazoles in the form of their alkali metal salts, such as sodium or potassium salts.

The active compounds used according to the invention, in which m represents 0, can also be obtained according to a further process as described in DOS 29 12 288 by the use of oxlrans of the general formula V

(V) in which

R @ 1 and R @ 1 are as defined above, in reaction with triazole in the presence of an alkali metal alkoxide such as sodium methoxide and in the presence of an inert organic solvent such as dimethylformamide at temperatures between 30 ° C and 100 ° C.

The triazolylmethylphenyl ketones of formula II are not yet known compounds. However, these compounds can be prepared in a conventional and known manner by reacting the corresponding phenylacyl halides (i.e., α-haloacetophenone derivatives) in reaction with a triazole in the presence of a diluent, such as dimethylformamide, and in the presence of an acid binding agent such as excess. triazole, at temperatures between 20 and 80 ° C.

The Grignard compounds of formula III are generally known organic chemistry compounds.

The 1-haloalkyl alkyl alcohols of formula IV have not been previously known. However, these compounds can be prepared in a conventional and known manner by reacting the corresponding phenacyl halides with the Grignard compounds of formula III according to process variant a).

The oxiranes of formula V have not yet been known. These compounds are the subject of the · Offenlegungsschrift 29 12 288 and can be obtained by the corresponding ketones are reacted either with dimethyloxasulfoniummethylidem known manner in the presence of diluents such as 0imethylsulfoxidu at temperatures between 20 and 80 ° C ^Ol Furthermore, the corresponding ketones can be reacted with trimethylsulfanium methylsulfate in a manner known per se in the presence of a two-phase system and optionally in the presence of a phase transfer catalyst at temperatures between 0 and 10 ° C.

All physiologically acceptable acids are suitable for the preparation of acid addition salts of the compounds of the formula I. These preferably include hydrohalic acids such as hydrochloric acid and hydrobromic acid, in particular hydrochloric acid, phosphoric acid, nitric acid, sulfuric acid, mono- and dibasic carboxylic acids and hydroxycarboxylic acids such as acetic acid, maleic acid, succinic acid. fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid, lactic acid, as well as sulfonic acids such as p-toluenesulfonic acid and 1,5-naphthalenedisulfonic acid.

Salts of the compounds of formula I may be obtained in a simple manner according to conventional salt-forming methods, for example by dissolving the compound of formula I in a suitable inert solvent and adding an acid, for example hydrochloric acid, and these salts are isolated in known manner, for example by filtration and optionally purified by washing with inert organic solvent.

The active compounds according to the invention have a strong microbial effect and can. be used for practical purposes to combat unwanted microorganisms. The active compounds are suitable as plant protection agents.

Fungicidal compositions are used in plant protection to combat fungi of the classes Plasmodiophoromyceles, Oomycetes, Chytridiomycetes, Zygornycetes, Ascomycetes, Basidiomycetes, Deuteromycetes.

The good plant tolerance of the active compounds according to the invention at the concentrations necessary to combat plant diseases permits the treatment of above-ground parts of plants, plants and seeds, as well as of the soil.

As plant protection agents, the active compounds according to the invention can be used with great success in combating fungi of the species Pcdosphaera, Uromyces and Erysiphe, as against the agent of powdery mildew (Po0αsphaera leucotricha), the agent of bean rust (Uromyces phaseoli) and Erysiphe cichoraceairum ·}, and good results are also achieved in combating cereal diseases such as cereal rust.

In certain application rates, the active compounds according to the invention also exhibit a good plant growth regulating effect.

The active compounds can be converted into the customary formulations such as solutions, emulsions, suspensions, powders, foams, pastes, granulates, aerosols, natural and synthetic substances impregnated with the active compounds, small particles coated with polymeric substances and coating materials for seeds, flammable additives such as smoke spirals and the like, as well as compositions in the form of concentrates of the active substance for cold or hot fog scattering.

These are prepared in known manner, for example by mixing the active compounds with extenders, that is liquid solvents, liquefied gases under pressure, and / or ^one solid carriers, optionally with the use of surfactants, that is emulsifiers and / or dispersants and / or foam-forming agents . If water is used as a filler, for example, organic solvents can also be used as co-solvents. Suitable liquid solvents are: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins such as petroleum fractions, alcohols, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexahone, strongly polar solvents such as dimethylformamide and dimethylsulfoxide, and water. By liquefied gaseous fillers or carriers is meant liquids which are gaseous at normal temperature and pressure, for example aerosol propellants such as halogenated hydrocarbons, as well as butane, propane, nitrogen and carbon dioxide. 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 solid carriers for the preparation of granulates are crushed and fractionated natural stone materials such as limestone, marble, pumice, sepiolite and dolomite. corn cobs and tobacco. stems. Suitable emulsifiers and / or foaming agents are non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, fatty alcohol polyoxyethylene ethers, e.g.

The compositions of the invention may include adhesives such as carboxymethylcellulose, natural and synthetic powdered, granular or latex polymers such as gum arabic, polyvinyl alcohol and polyvinyl acetate.

It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as ¹ alizarin dyestuffs and metal azo-phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper , cobalt and molybdenum and zinc.

The concentrates generally comprise between 0.1 and 95% by weight, preferably between 0.5 and || 90% by weight of active ingredient. й

The active compounds according to the invention may be present in the formulations in admixture with other known active compounds, such as fungicides, bactericides, insecticides, acaricides, nematocides, herbicides, avian protective agents, growth agents, plant nutrients. with soil conditioners.

The active compounds according to the invention can be applied as such, in the form of concentrates or by further dilution of the ready-to-use dosage forms, such as ready-to-use solutions, emulsions, suspensions, powders, pastes and in a manner such as watering, dipping, spraying, fogging, evaporation , in the form of suspensions, coating, dusting by tossing, dry pickling, wet pickling, wet pickling or suspension or incrustation.

In the treatment of plant parts, the concentrations of the active ingredient in the dosage forms can vary within wide limits. They are generally between 1 and 0.0001% by weight, preferably between 0.5 and 0.001% by weight.

In the treatment of seed, the active compound is generally required in an amount of from 0.001 to ≥ 50 g per kg of seed, preferably 0.01 to 10 g.

In soil treatment, active compound concentrations of from 0.00001 to 0.1% by weight, preferably from 0.0001 to 0.02% by weight, are required at the point of action.

In the following examples, the following compounds were used as comparators:

7/2

Protective test for apple powdery mildew (Podosphaera)

Solvent: 4.7 parts by weight of acetone

Water: 95.0 parts by weight

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

The spray liquid is sprayed until the young apple seedlings having 4 to 6 leaves are wet. The plants are kept for 24 hours in a greenhouse at 20 ° C and 70% relative humidity. The plants are inoculated by dusting with conidia of Podosphaera leucotricha and placed in a greenhouse where they are stored at 21-23 ° C and 70% relative humidity.

infestation of the seedlings is observed on days after inoculation. The values obtained are converted to percent attack. 0 ° / o means no infection, 1010% means that the plants are completely infected.

In this test, for example, the following compounds of the invention show a very good effect, which clearly exceeds that of the prior art compounds, i.e. compounds A and B: the compounds of Examples 1 and 3.

Emulsifier: 0.3 part by weight of alkylaryl polyglycol ether

Table A

Protective test for apple powdery mildew (Podosphaera)

Active substance Infestation in ° / o at an active compound concentration of 0.001%

100 (A) (known)

100 mm (1)

Infestation in% at active compound concentration

0.001% (2)

Active substance

Example B

Test na. powdery mildew (Erysiphe) protective effect (• cucumbers)

Solvent: 4.7 parts by weight of acetone

Emulsifier: 0.3 part by weight of alkylaryl polyglycol ether

Water: 95.0 parts by weight

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

The spray liquid is sprayed until the young cucumber plant having about 3 leaves is wet. The cucumber plants are kept in the greenhouse for 24 hours. to dry. Then. dusts for inoculation with conidia of Erysiphe cichoracearum. The plants are then kept in a greenhouse at a temperature of 23-24 ° C and a relative air humidity of about 75%.

The infestation of cucumber plants is determined for 12 days. The values obtained are converted to percent attack. 0% means no attack, 1'00% means that plants are completely attacked.

In this test, for example, the following compounds of the invention exhibit a very good effect which exceeds that of compounds C and D known in the art: compounds of the embodiments: 1, 7, 10, 12, 14 and 5.

TableB

Powdery mildew test [Erysiphe] - protective effect (cucumbers)

Active substance Contamination in. % at active substance concentration 0,005%

OH

CH-CHfN ^ N ' ¹ (C) (known)

(1)

Active substance

Infestation in% at active ingredient concentration 0.005%

100 ALIGN!

(14)

OH _-

(5)

1B

Example C

Test for bean rust (Uromyces phaseoli) - protective effect

Solvent: 4.7 parts by weight of acetone

Emulsifier: 0.3 part by weight of alkylaryl polyglycol ether

Water: 95.0. weight part

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

The bean plants in the 2-leaf stage are sprayed with the spray liquid until dripping. The plants are left to dry in a greenhouse for 2.4 hours at a temperature of 20-22 ° C, and at a relative air humidity of 70%. They are then inoculated with an aqueous suspension of bean rust uredospores (Uromyces phaseoli) and incubated for 24 hours in a dark humid chamber at 20-22 ° C and 100% relative humidity.

The plants are then kept in a greenhouse at 20 [deg ^.] C. under intense lighting ^. up to 22 ° C and a relative air humidity of 70 ^; up to 80% · for 9 days.

days, inoculation revealed rorflin attack. The values obtained are converted to · percent of attack. 0% means no attack and 100% means complete attack.

In this test, for example, the following compounds of the invention show a very good effect, which clearly exceeds that of the known compound E: the compounds of Examples 12, 14 and 5.

Table C

Test for bean rust (Uromyces phaseoli) - protective effect

Active substance Infestation in% at active substance concentration

0.001%

OH / ¹ Q / N ^C

100 ALIGN!

(E) (known)

Cl

(5)

Example D

Protective test (shoot treatment) for Erysiphe graminis var. hordei (leaf-destroying mycosis)

To prepare a suitable active ingredient, 0.25 parts by weight of active ingredient is mixed in 2.5 parts by weight of dimethylformamide and 0.06 parts by weight of alkylaryl polyglycol ether as emulsifier, and 975 parts by weight of water are added. The concentrate obtained is then diluted with water to the desired final concentration.

To determine the protective effect, young barley plants (Amsel species) in one leaf stage are sprayed to the moistening with the active ingredient prepared and, after drying for 18 hours, dusted with spores of Erysiphe graminis var. hordei.

After 6 days when the plants are grown at 21-22 ° C and 80-90% air humidity, the extent of the disease on the plants is evaluated. The degree of infestation is expressed as the percentage of infestation of the untreated control plants, with 0% indicating no infestation and 100% the same infestation as the untreated control plants. The lower the degree of attack, the more effective the test substance is.

In this test, for example, the following compounds of the invention show a very good effect which clearly exceeds that of compounds D and F known in the art: the compounds of Examples 1, 3, 7, 10, 12, 14 and 5.

T a b u 1 к a D

Protective test (shoot treatment) for Erysiphe graminis var. hordei (leaf-destroying mycosis)

Active substance

Concentration of the active ingredient in the spray suspension in% by weight.

Infection in% of untreated control

0.025 100 (D) (Known)

0,025 100

0,025

(1)

Infection in% of untreated 'controls

Concentration of the active substance in the spray suspension in% hmoit.

Active substance

0,025

0,025

0,025

0,025

0,025

3.8

12.5

16.3

12.5

10.3

0,025

11,3 mm (5)

Example E

Rust test '' Puccinia recondita - '' (leaf-destroying mycosis) - treatment of plant shoots - - (protective effect)

To produce a suitable preparation of active compound, 0.25 part by weight of active compound was taken up in 25 parts by weight of dimethylformamide and '0.00 Part of ^alkylaryl: ERO emulsifier and added' 975 parts by weight of water. The concentrate is diluted with water to the desired final spray suspension concentration.

To determine the protective activity, young Michigan Amber wheat plants are inoculated at one leaf stage with a suspension of uredospores of Puccinia recondita rust in 0.1% aqueous agar. After drying the spore suspension, the wheat plants are sprayed until moistened with the active preparation and placed in a greenhouse for 24 hours at about 20 ° C and 100% relative humidity for incubation.

After 10 days of plant growing at 20 ° C and 80-90 percent relative humidity, rust control of the plants was evaluated. The degree of infestation is expressed as the percentage of infestation of untreated control plants. Here, '0%' means no infestation and '100' percent means the same degree of infestation as' untreated control plants. The active substance is the more effective the lower the rust attack.

In this test, for example, the following compounds of the invention show a very good effect, which clearly exceeds that of compound D known in the art: the compounds of Examples 8, 12, 14 and 5.

Table E

Puccinia recondita rust test - (leaf-destroying mycosis) - treatment (protective effect) of plant shoots

Active substance

Concentration of the active ingredient in the spray suspension in% by weight.

Infestation in% of untreated control attack

0.025 83.3 (D) (known)

OH

0.025 3.8

CH, I Λ

(14)

0.025, 0.0

0.025 0.0

Infestation in% of untreated control

Concentration of the active ingredient in the spray suspension in% by weight.

Active substance

0.025 16.3 (5)

The examples illustrate a process for producing the active ingredient:

Examples 1 and 2

&

Az

A / ^ ^N

A-J example ^: la

A ^z --N. | EXAMPLE 2.

(Procedure b)

To a solution of 3.5 g (0.065 mol) of sodium methoxide in 18 ml of methanol was added

7.6 g (0.11 mol) of 1,2,4-triazole. Then a solution of 19.5 g (0.05 mol) of 2 * (4-biphenylyl) -3-chloro-1- (2,4-dichlorophenyl) propan-2-ol in 38 ml of dimethylformamide is added dropwise and The mixture was heated at 70 ° C for 90 minutes. The solvent was removed in vacuo on a rotary evaporator and the residue was stirred with water. The resulting crystals were washed with diethyl ether and recrystallized from acetonitrile. 2.2 g of 2- (4-η 4 - (4-β-β-η 4)) -1- (2,4-dichlorophenyl) -3t (1,2,4-triazol-4-yl) propane- M.p. 260 DEG.

Acetonitrile solution. (mother liquor). It is evaporated and the crystals obtained are washed with diethyl ether and ethyl acetate. 6.5 g of 2- (4-biphenylyl) -1- (2,4-dichlorophenyl) -3- (1,2,4-triazol-1-yl) poopan-2-ol are obtained, m.p. · 124 degrees Celsius.

Production of starting material:

čn> i * Cl

To a solution of 0.6 mol of 2,4-dichlorobenzylmagnesium chloride obtained from 15.9 g (0.65 mol) of magnesium and 117.3 g (0.6 mol) of 2,4-dichlorobenzyl chloride in 300 ml of ether is added 69 3 grams (0.3 mol) of 4-phenylphenacyl chloride (in parts). The reaction mixture is then poured onto an aqueous ammonium chloride solution, the ether phase is separated, washed with water, dried over sodium sulphate and evaporated. The residual oil is extracted with petroleum ether and the solution in petroleum ether is evaporated. The crystals are · filtered off and dried. 62 g (53% of theory) of 2- (4-biphenylyl) -3-chloro-1- (2,4-dichlorophenyl) propan-2-ol are obtained, m.p. 84 ° C.

Examples 3 and 4 <§НО> с-№ _г ^ О>

Az

A 2 Σ-Μ I = example 3 ^ J = J

^{Example 4} (Procedure b)

To a solution of sodium methoxide (17.9 g, 0.33 mol) in methanol (90 ml) was added 1,2,4-triazole (38.3 g, 0.56 mol). A solution of 82 g (0.254 mol) of 2- (4-biphenyl) -3-chloro-1-phenylpropan-2-ol in 191 ml of dimethylformamide was then added dropwise and the mixture was heated at 60 ° C for 90 minutes. The solvent was removed in vacuo on a rotary evaporator. The residue was dissolved in methylene chloride and washed with water. The methylene chloride solution was dried over sodium sulfate, filtered and concentrated in vacuo. The oil obtained is chromatographed. There were obtained 13.8 g of 2- (4-biphenylyl) -1-phenyl-3- (1,2,4-triazol-1-yl) propan-2-ol, m.p.

2.7 g of 2- (4-biphenylyl) -1-phenyl-3- (1,2,4-triazol-4-yl) propan-2-ol, m.p. 246 ° C.

Production of starting material:

14.96 g (0.22 mol) of triazole is then added dropwise a solution of 40 g (0.1 mol) of 1- (2'-chloro-4-biphenyl) -2-chloro-1- (4-chlorophenyl) ethanol in 75 ml of dimethylformamide and the mixture is heated at 70 DEG C. for 3 hours, the reaction mixture is concentrated by distilling off the solvent in vacuo and the residue is triturated with water, and the residual crystals are washed with acetonitrile and recrystallized. (2'-chloro-4-biphenylyl) -1- (4-chlorophenyl) -2- (1,2,4-triazol-1-yl) ethanol, m.p. 190 ° C.

Production of starting material:

i Ct

From 10.69 g (0.44 mol) of magnesium, 76.6 g (0.4 mol) of 4-bromochlorobenzene and 53 g (0.2 mol) of 4- (2-chlorophenyl) phenacyl chloride were obtained analogously to Example 1 75 g of 1- (2'-chloro-4-biphenylyl) -2-chloro-1- (4-chlorophenyl) ethanol.

To a solution of the benzylmagnesiurachloride obtained from 24.3 g (1 mol) of magnesium and 115 ml (1 mol) of benzyl chloride in 150 ml of diethyl ether was added portionwise 115.3 g (0.5 mol) of 4-phenylacyl chloride. The reaction mixture was heated at reflux for 90 minutes and then poured into aqueous ammonium chloride solution. The separated ether phase is washed with water, dried over sodium sulphate and concentrated. Remaining oil is mixed with petroletherein to crystallize. 50 g (31% of theory) of 2- (4-biphenylyl) -3-chloro-1-phenylpropan-2-ol of melting point 96 DEG C. are obtained.

Example 5

(Procedure b)

COCH2Ct

To a solution of 377 g (2 mol) of 2-chlorobiphenyl in 160 ml (2 mol) of chloroacetyl chloride and 1000 ml of methylene chloride was added 2: 93.7 g (2.2 mol) of aluminum chloride (in portions). After 18 hours, the reaction product was poured onto ice and hydrochloric acid. The organic phase is separated, dried over sodium sulphate and concentrated in vacuo by distilling off the solvent. The residual oil is purified by distillation. It is obtained

478.7 g (90% of theory) of 4- (2-chlorophenyl) -phenacyl chloride, m.p.

The following compounds of formula I can be prepared in an analogous manner to that described in Examples 1 to 5

OH ch ₄

Az li>

To a solution of 7.02 g (0.13 mol) of sodium methoxide in 36 ml of methanol is added

Example R number

R ¹

Az m Melting point (° C) or refractive index

6 ⁴ Χθ> 7 -@-Whose" 8 C4 9 - / O> -s. 10 - <O> targets. ct  steed ni Cl · <ф « 12 13 14 Cl & 4 - ^^ - 15 Dec 16 17 <oý 18 1J and 7o>

/ zzN -N I ^ -N 1 250 / = h -N N- / = h 1. 1 104 Λ-J 1 144 л-J rzN 1 175 Λ-J -N ^ 1 = 1.5992 Yi- and 1 160 -N J ./ primarilyN 1 0 189 “4 Y / xJ l 0 217 -v -aT ⁿ | 0 144 , z = V '4 w 0 164 0 0 .170 160 -N = _t 1 J 0 220

Claims (1)

A fungicidal composition, characterized in that it contains at least one hydrocyl-alkyl-trlazole of the formula I ^R nu as an active ingredient. X oh \ № X Az U) in which Az is triazolyl, R is optionally one or more halogen-substituted phenyl groups, R 1 is an optionally substituted phenyl group one or more times halogen, m is 0 or 1, or a physiologically acceptable acid addition salt thereof.