DD151039A5 - FUNGICIDAL AGENTS - Google Patents

Abstract

The invention relates to the use of hydroxyalkyl triazoles as fungicides. The compounds of general formula I in which Az, R, R & exp1! and R & exp2! have the meaning given in the description are suitable for use as pesticides. They can be used with particular success to combat Podosphaera-, Uromyces- u. Erysiphe species are used, such as against the causative agent of the real apple downy mildew (Podospaera leucotricha), the causative agent of the bean rust (Uromycesphaseoli) and against the causative agent of the cucumber powdery mildew (Erysiphe cichoacearum).

Description

Berlin, August 25, 1980 221140 """'* _{57 105 1 ±}

Fungicidal agent

Field of application of the invention

The present invention relates to the use of hydroxyalkyl triazoles as fungicides.

Characteristic of the known technical solutions

It has already been disclosed that phenyl-2-triazolyl-1-ethanols which have been substituted in the phenyl moiety have good fungicidal properties (cf. German Offenlegungsschrift No. 2,431,407). However, their activity is not always complete, especially at low application rates and concentrations satisfying.

aim the invention

Surprisingly, the hydroxyalkyl-triazoles of the formula (I) which can be used according to the invention have a better fungicidal activity than the substituted 1-phenyl-2-triazolyl-1-ethanols known from the prior art, which are chemically and functionally obvious compounds. The substances which can be used according to the invention thus represent an enrichment of the art.

Dar interpretation of the nature of the invention _i

It has been found that the hydroxyalkyl-triazoles of the general formula

57 105

1

R ¹

OH

az

in which

Az stands for triazolyl,

R is optionally substituted phenyl, naphthyl or tetrahydronaphthyl,

R is optionally substituted phenyl or cycloalkyl and

R is hydrogen or

12

R and R together in the o-position to one another represent an optionally substituted, multi-membered methylene bridge or together with the phenyl ring for naphthyl,

R is halogen, alkyl, alkoxy or haloalkyl,

η is O, 1, 2 or 3 and m is O or 1,

and their physiologically acceptable acid addition salts have good fungicidal properties *

22114

Of the hydroxyalkyltriazoles of the formula (I) which can be used according to the invention those are preferred in which Az_ is 1,2,4-triazol-1-yl or 1,2,4-triazol-4-yl, R is optionally substituted phenyl, naphthyl or tetrahydronaphthyl, where as substituents preferably: halogen, in particular fluorine, chlorine and bromine, straight-chain or branched alkyl and alkoxy having in each case 1 to 4 carbon atoms, and halogenoalkyl having 1 to 4 carbon and up to 5 halogen atoms, in particular with 1 or 2 carbon and up to 3 identical or different halogen atoms, halogens being in particular fluorine and chlorine, for example trifluoromethyl may be mentioned; R ¹ is unsubstituted or unsubstituted phenyl or cycloalkyl having 3 to 7 carbon atoms, preferably being mentioned as substituents: halogen, in particular fluorine, chlorine or bromine, alkyl having 1 to 4, in particular having 1 to 2 carbon atoms, and alkenyl having 2 to carbon atoms and R ^{2 is} hydrogen, or R ¹ and. R ² together in ortho-position to one another represent an optionally mono- or polysubstituted methylene bridge having 3 to 5 methylene groups, preference being given to substituents:

Halogen, in particular fluorine, chlorine or bromine, and alkyl having 1 to 4, in particular having 1 to 2 carbon atoms; or together with the phenyl ring for naphthyl; R ^{3 is} halogen, in particular fluorine,

Le A 19 63 6

2 2 1 1 Λ Ο - 4 -

Chlorine or bromine, straight-chain or branched alkyl and alkoxy having in each case 1 to 4 carbon atoms and halogenoalkyl having 1 to 4 carbon atoms and up to 5 halogen atoms, in particular having 1 or 2 carbon atoms and up to 3 identical or different halogen atoms, halogens being in particular fluorine and chlorine, for example, trifluoromethyl is called; the index η stands for the numbers 0, 1 or 2 and the index m stands for the numbers 0 or 1. Very particular preference is given to those compounds of the formula (I) in which Az has the abovementioned meaning, R is phenyl which is optionally monosubstituted or disubstituted, identically or differently, by chlorine, fluorine or methyl, naphthyl and tetrahydronaphthyl; R ^{1 is} phenyl, cyclopentyl or cyclohexyl, these radicals may optionally be monosubstituted or disubstituted by chlorine, bromine, fluorine, methyl, ethyl, isopropyl or isopropenyl; and R ^{2 is} hydrogen, or R ¹ and R ² are ortho to each other, a tri-, tetra- or pentamethylene bridge, - optionally substituted by chlorine or methyl, or together with the phenyl ring is naphthyl; R ^{3 is} chlorine, fluorine or methyl, η is 0 or 1 and m is 0 or 1.

Specifically, in addition to the compounds mentioned in the preparation examples, the following compounds of the general formula (i) may be mentioned (Az_ being in each case 1,2,4- or 1,3,4-triazol-1-yl):

^R1 OH

R * __ ^ - C- (CH ₂ ) _m -R (I)

CH ₂

Le A 19 636

22114

R ² R ³ .

Cl. Ci.

Cl

O-ci

Cl

Cl Cl

F Cl

Le A 19

KG)

4- C

Cl.

CH,

Cl

H O H O H O H O

H H H H H H H

0 0 0 0 0 0 0 0 0 0 0

114

RR ¹

- 6 -

Rm

-Cl

 ο

Cl

Cl

Cl

he

Cl

Cl

-Cl

Cl

⁴ ^

Cl

4- (Η

3,4- (CH ₂ 3,4- (CH ₂

4- (η)

4-6? 4

H H H H H H H

H H H H H

O O O O O O O O O O

O O O O O

Le A 19 636

R ¹

R ^{2 R3} n m H - Q H - O H - 1 H 1

Cl F

Cl F Cl

Cl "Clv.

-Q

Cl Cl Cl

Cl

Cl 4

4- (H

4

CH ₃

CH ₃

4- <P> -C ₃ H ₇ -i

H 1 H 1 H 1 H 1 H 1 H 1 H 1 H 1 H 1 H 1

Le A 19

22

R ² R ³ _n m

> -Cl

-Cl

4- (H

3,4- (CH ₂ ) ₃ -3,4- (CH ₂ ) ₄ -

-Cl

-Cl

H H H H H H H H H H

H H H

19

22 1

LC.

Cl

Cl 'Cl

-Cl

-Q-

-F F

R ¹

4-0-Cl 4 - ^ - Cl

4

4- <H>

3,4- (CH ₂ ) ₄ 3,4- (CH ₂ ) ₃ R ² R ³ .

Le A 19

22 1140 - ίo-

The active compounds to be used according to the invention and their acid addition salts have not yet been described. However, the substances and their preparation are the subject of-own earlier applications (see German Patent Applications P 28 51 086 / Le A 19 2727 of 25.11.1978,

and P 28 51 116 / Le A 19 273? of 25.11.1978); and can be prepared by the methods described therein by

a) triazolylmethylphenyl ketones of the formula

0 R ² -j £ (- \)} - C - CH ₂ - Az (II)

in which

Az, Ri _f R2, R ^ and η are as defined above

to have,

with a Grignard compound of the formula

R - (CH ₂ ) _m - Mg - X (III)

in which

R and m are as defined above and

X for halogen, in particular chlorine

or bromine stands,

Le A 19 636

Currently i * »U - 11 -

in the presence of a conventional for a Grignard reaction solvent, such as preferably ether, at temperatures between about 30 to about 80 ⁰ C, or

b) 1-halo-alkyl alcohols of the formula

- R

(IV)

in which

R, R1, Ra η and m

have the meaning given above and

is halogen, in particular chlorine or bromine,

with triazole, if appropriate in the presence of an acid binder, 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 ⁰ C, preferably at the boiling temperature of the solvent. In some cases, it is advantageous to use the triazoles in the form of their alkali metal salts, such as the sodium or potassium salt.

The active compounds to be used according to the invention in which the index m is O can also be obtained by a further process, which, however, likewise has not yet been described (cf German Patent Application P 29 12 288.1 ^ Le A 19 527 of 28.3 .1979), by

Le A 19 636

22 1 UO - η-

c) oxiranes of the formula

(V)

in which R, R ¹ , R ² ,

R ³ and η are as defined above

to have,

with triazole in the presence of an alkali metal such as sodium methylate and in the presence of an inert organic solvent such as dimethylformamide, at temperatures between 30 and 100 ⁰ C implemented.

The triazolylmethyl-phenyl ketones of the formula (II) are not yet known. However, they can be prepared in a generally customary and known manner by corresponding phenacyl halides (which are oL-halo-acetophenone derivatives) with triazole in the presence of a diluent, such as dimethylformamide, and in the presence of an acid-binding agent, in particular an excess of Triazole, reacted at temperatures between 20 and 8O ° C.

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

The 1-haloalkyl alcohols of the formula (IV) are not yet known. However, they can be prepared in a generally customary and known manner by reacting corresponding phenacyl halides with Grignard compounds of the formula (III) according to process variant (a)

 Le A 19 636

2 2 1

The oxiranes of the formula (V) are not yet known. They are also the subject of the aforementioned prior application (see German Patent Application P 29 12 288.1 ILe A 19 527 / of 28.3.1979) and can be obtained by reacting corresponding I'etone either with dimethyloxosulfonium methylid in

known manner in the presence of a diluent such as .Dimethylsulfoxid, reacted at temperatures between 20 and 80 ⁰ C; or with trimethylsulfonium methyl sulfate in a conventional manner in the presence of a two-phase system and optionally in the presence of a phase transfer catalyst at temperatures between 0 and 100 ⁰ C.

For the preparation of acid addition salts of the compounds of formula (i) are all physiologically acceptable acids in question, These include preferably the hydrogen halides, such. the hydrochloric acid and the hydrobromic acid, in particular the hydrochloric acid, furthermore phosphoric acid, nitric acid, sulfuric acid, mono- and bifunctional carboxylic acids and hydroxycarboxylic acids, such. Acetic, maleic, succinic, fumaric, tartaric, citric, salicylic, sorbic, lactic and sulfonic acids, e.g. p-toluenesulfonic acid and 1,5-naphthalenedisulfonic acid.

The salts of the compounds of formula (I) can be readily prepared by conventional salt formation techniques, e.g. by dissolving a compound of formula (I) in a suitable inert solvent and adding the acid, e.g. Hydrochloric acid, and in a known manner, e.g. by filtration, isolated and optionally purified by washing with an inert organic solvent.

Le A 19 636

22 1 1 Λ Ο

The active compounds according to the invention have a strong microbicidal action and can be used practically for controlling unwanted microorganisms. The active ingredients are suitable for use as plant protection agents.

Fungicides in crop protection are used to. Control of Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes.

The good plant tolerance of the active ingredients in the necessary concentrations for controlling plant diseases allows treatment of aboveground. Plant parts, of plant and seed, and of the soil.

As plant protection agents, the active compounds according to the invention can be used with particularly good success for controlling Podosphaera-, Uromyces- and Erysiphe species, such as against the pathogen of true apple powdery mildew (Podosphaera leucotricha), the pathogen of the bean rust (Uromyces phaseoli) and against the causative agent of the cucumber powdery mildew (Erysiphe cichoacearum;) Good results are also achieved in the control of cereal diseases such as powdery mildew and grain rust.

At certain application rates, the active compounds according to the invention also have a growth-regulating action.

Le A 19 636

22114

The active compounds can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, active substance-impregnated natural and synthetic substances, microencapsulations in polymeric substances and in seed coating compositions, furthermore in formulations with Fuel packs, such as smoke cartridges, cans, spirals and others, as well as ULV-KaIt and warm mist formulations.

These formulations are prepared in a known manner, e.g. by mixing the active compounds with extenders, that is to say liquid solvents, liquefied gases under pressure and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-forming agents. In case of using water as an extender, e.g. also organic solvents can be used as auxiliary solvents. Suitable liquid solvents are essentially: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. Petroleum fractions, alcohols, such as butanol or glycol, and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide, and water; By liquefied gaseous diluents or carriers is meant those liquids which are gaseous at normal temperature and under normal pressure, e.g. Aerosol propellant, such as halogenated hydrocarbons, butane, propane, nitrogen

Le A 19 636

2 2 1 ILO

and carbon dioxide; as solid carriers are: 2.B. ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica. Alumina and silicates; suitable solid carriers for granules are: e.g. crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; suitable emulsifiers and / or foam formers are: e.g. nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates; suitable dispersants are: e.g. Lignin-sulphite liquors and methylcellulose.

Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-type polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate may be used in the formulations.

Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azole metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

The formulations generally contain between 0.1 and 95% by weight of active ingredient, preferably between 0.5 and 90%.

Le A 19 636

The active compounds according to the invention may be present in the formulations or in the various application forms in admixture with other known active compounds, such as fungicides, bactericides, insecticides, acaricides, nematicides, herbicides, bird repellants, growth factors, plant nutrients and soil conditioners.

The active compounds can be used as such, in the form of their formulations or the use forms prepared therefrom by further dilution, such as ready-to-use solutions, emulsions, suspensions, powders, pastes and granules. The application is done in the usual way, e.g. by pouring, dipping, spraying, spraying, atomizing, vaporizing, injecting, silting, spreading, dusts, spreading, dry pickling, wet pickling, wet pickling, slurry pickling or encrusting.

In the treatment of parts of plants, the drug concentrations in the use forms can be varied within a substantial range. They are generally between 1 and 0.0001% by weight, preferably between 0.5 and 0.001 %.

In the seed treatment, in general, amounts of active ingredient of 0.001 to 50 g per kilogram of seed, preferably 0.01 to 10 g, needed.

When treating the soil, drug concentrations of 0.00001 to 0.1% by weight, preferably 0.0001 to 0.02%, are required at the site of action.

Le A 19 636

2 2 1

In the following examples, the compounds indicated below are used as comparative substances:

-CH-CH ₂ -N

(A)

5 (B) Cl-OQ) -CH-CH ₂ -Ij ₁

OH

(C) Br- "Y-CH-CH ₂ -N

(D) Cl- {Q> -CH-CH _a -NJ

? ^H

(E) H ₃ C- (C) VCH-CH ₂ -N

Cl

OH

(F) CIhQ

χ 1/2

Cl

SO, H

Le A 19 636

22 1 140

Example A

Podosphaera test (apple) / protective

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 for the desired active ingredient concentration in the spraying liquid is mixed with the stated amount of the solvent and the concentrate is diluted with the stated amount of water which contains the additives mentioned.

With the spray liquid splashed young apple seedlings, which are in the 4- to 6-leaf stage, to dripping wet. The plants remain for 24 hours at 2O ⁰ C and a relative humidity of 70 % in the greenhouse. They are then inoculated by dusting with conidia of the powdery mildew pathogen (Podosphaera leucotricha) and used in a greenhouse with a temperature of 21 to 23 ⁰ C and a relative humidity of 70 % .

Ten days after the inoculation, the infestation of the seedlings is determined. The obtained rating values are converted into percent infestation. 0 % means no infestation, 100 % means that the plants are completely infested.

In this test, e.g. the following compounds a very good effect, which is clearly superior to those of the known from the prior art compounds (A) and (B): Compounds according to Preparation Examples 1 and 3 ·

Le A 19 636

221U0 - 2o -

Example B

Erysiphe test (cucumbers) / Protective

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 for the desired active ingredient concentration in the spraying liquid is mixed with the stated amount of the solvent and the concentrate is diluted with the stated amount of water which contains the additives mentioned.

The spray liquid sprays young cucumber plants with about three leaves to dripping wet.

The cucumber plants remain for drying in the greenhouse for 24 hours. Then they are pollinated with conidia of the fungus Erysiphe cichoracsarum for inoculation. The plants are then placed at 23 to 24 ⁰ C and at a relative humidity of about 75 % in the greenhouse.

After 12 days, the infestation of cucumber plants is determined. The obtained rating values are converted into percent infestation. O % means no infestation, 100 % means that the plants are completely infested.

In this test, e.g. the following compounds have a very good effect superior to those of the compounds (C) and (D) known in the art:

Compounds according to Preparation Examples: 1,7,10,12, 14 and 5.

Le A 19 636

2 2 11 ^ 0 - 21 -

Example C

Urbmyces test (bean rust) / protective

Solvent: 4.7 parts by weight of acetone

Emulsifier: 0.3 parts by weight of alkylaryl polyglycol ether Water: 95.0 parts by weight

The amount of active ingredient required for the desired active substance concentration in the spray liquid is mixed with the stated amount of the solvent and the concentrate is diluted with the stated amount of water which contains the additives mentioned.

With the spray liquid splashed the young bean plants, which are in the 2-leaf stage, to dripping wet. The plants remain for drying 24 hours at 20-22 ⁰ C and a relative humidity of 70% in the greenhouse. Subsequently, they are inoculated with an aqueous uredospore suspension of the bean rust pathogen (Uromyces phaseoli) and incubated for 24 hours in a dark moist chamber at 20-22 ⁰ C and 100% relative humidity.

The plants are then grown under intense lighting for

9 days at 20-22 ⁰ C and a relative humidity of 70-80% in the greenhouse set up.

10 days after the inoculation, the infestation of the plants is determined. The obtained rating values are converted into percent infestation. 0% means no infestation, 100 % means that the plants are completely infested.

In this test, e.g. the following compounds a very good effect, which is clearly superior to that of the known from the prior art compound (s) (E):

Compounds according to Preparation Examples 12, 14 and 5 "Le A 19 636

22 1 1 40 - 22 -

Example D

Sprout Treatment Test / Mildew / Protective (Foliar Mycosis)

To prepare a suitable preparation of active compound, 0.25 part by weight of active compound in 25 parts by weight of dimethylformamide and 0.06 part by weight of emulsifier (alkylaryl polyglycol ether) are added and 975 parts by weight of water are added. The concentrate is diluted with water to the desired final concentration of the spray mixture.

To test for protective activity, the monocled barley seedlings of the variety Amsel are sprayed with the preparation of active compound dewatered. After drying, the barley plants are dusted with spores of Erysiphe graminis var.hordei.

After 6 days dwell time of the plants at a temperature of 21-22 ° C and a humidity of 8O-9O? O evaluating the stocking of plants with mildew pustules. The level of infestation is expressed as a percentage of the infestation of the untreated control plants. 0 % means no infestation and 100 % the same degree of infestation as in the untreated control. The lower the powdery mildew case, the more effective the active ingredient.

, In this test, e.g. the following compounds a very good effect, which is clearly superior to those of the known from the prior art compounds (d) and (F): Compounds according to Preparation Examples 1,3,7,10,12, 14 and 5

Le A 19 636

22 11 AO - 23 -

Example E

Sprout treatment test / grain rust / protective (leaf-destroying mycosis)

To prepare a suitable preparation of active compound .. takes 0.25 parts by weight of active compound in 25 parts by weight of dimethylformamide and 0.06 parts by weight of emulsifier alkylaryl polyglycol ether and are 975 parts by weight V / asser added. The concentrate is diluted with water to the desired final concentration in the spray mixture.

In order to test for protective activity, one cultivars one-leaved Michigan Amber wheat plants with a uredospore suspension of Puccinia recondita in 0.1% water agar. After drying of the spore suspension was sprayed, the wheat plants with the preparation of active compound until dew-moist, and provides it to incubate for 24 hours at about 20 ⁰ C and a 100% humidity in a greenhouse.

After 10 days residence time of the plants at a temperature of 20 ⁰ C and a humidity of 80-SO % is evaluated, the stocking of the plants with rust pustules. The degree of infestation is expressed as a percentage of the infestation of the untreated control plants. Here, 0 % means no infestation and IOC % the same Eefallsgrad as in the untreated control. The active ingredient is the more effective, the lower the rust attack.

In this test show. the following compounds have a very good effect, that of the compound known from the prior art. (d) clearly. is superior: compounds according to Preparation Examples 8,12,14 and 5.

Le A 19 636

22 1 1 40

Preparation Examples Example 1 and 2

- 24 -

-Cl

Az = -

example 1 Example 2

(Method b)

A solution of 3.5 g (0.065 mol) of sodium methylate in 18nl of methyl alcohol is added 7.6 g (0.11 mol) of 1,2,4-triazole; Subsequently, 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 90 minutes on 7O ⁰ C heated. The solvents are removed in vacuo on a rotary evaporator and the residue is stirred with water. The resulting crystals are washed with diethyl ether and recrystallized from acetonitrile. This gives 2.2 g of 2- (4-biphenylyl) -1- (2,4-dichlorophenyl) -3- (l, 2,4-triazol-4-yl) propan-2-ol of melting point 260 ^° C. The acetonitrile solution (mother liquor) is evaporated and the resulting crystals are washed with diethyl ether and sat. This gives 6.5 g of 2- (4-3iphenylyl) -1- (2,4-dichlorophenyl) -3- (1,2,4-triazol-1-yl) -propan-2-ol of melting point 124 ^° C.

Le A 19 636

22 1 1

Preparation of the starting product

To a solution of 0.6 mol of 2,4-dichlorobenzyimagnesium chloride, obtained from 15 g of (0.65 mol) of magnesium and 117.3 g (0.6 mol) of 2,4-dichlorobenzyl chloride in 300 al of ether, becomes 69 , 3g (0.3 mol) of 4-phenylphenacyl chloride added in portions. Subsequently, the reaction mixture is poured into aqueous ammonium chloride solution, the ether phase separated, washed with water, dried over sodium sulfate and evaporated. The remaining OeI is extracted with petroleum ether and the petroleum ether solution 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 of melting point 84 ^° C. are obtained.

For all 3 and 4

Az β -Ν

CTN

Az = -N, \ = - N

Le A 19 636

= Example 3

= Example 4

22 1 U

(Method b)

To a solution of 17.9 g (0.33 mol) of sodium methylate in 90 ml of methyl alcohol is added 38.3 g (0.56 mol) of 1,2,4-triazole; Subsequently, a solution of 32g (0.254 mol) of 2- (4-biphenylyl) -3-chloro-1-phenyl-propan-2-ol in 191 ml of dimethylformamide is added dropwise and heated to 60 ⁰ C for 90 minutes. The solvents are removed in vacuo on a rotary evaporator; the residue is dissolved in methylene chloride and washed with water. The methylene chloride solution is dried over sodium sulfate, filtered and concentrated in vacuo. The resulting OeI is separated by chromatography. This gives 13, Sg 2- (4-Bipher.y IyI) -l-phenyl-3- (1,2,4-triazol-1-yl) -prcpan-. 2-ol of melting point 124 ⁰ C and 2.7 g of 2- (4-biphenyl) -I-phenyl-3- (l, 2,4-triazol-4-yl) -prcpan-2-ol of melting point 246 ⁰ C. ,

To a solution of benzylmagnesium chloride obtained from 24.3 g (i mol) of magnesium and 115 ml (1 mol) of ezyl chloride in 150 ml of diethyl ether, 115.3 g (0.5 mol) of 4-phenylphenacyl chloride are added by the method. The reaction mixture is refluxed for 90 minutes and then poured onto aqueous ammonium chloride solution. The separated ether phase is washed with water, dried over sodium sulfate and concentrated. The remaining OeI is brought to crystallization by stirring with petroleum ether. This gives 50 g (31 % of theory) of 2- (4-biphenylyl) -3-chloro-1-phenyl-propan-2-ol of melting point 96 ^° C.

Le A 19 636.

Example 5

(Method b)

To a solution of 7, O2g (0.13 mol) of sodium methylate in 36 ml of methyl alcohol is added 14.96 g (0.22 mol) of triazole. Subsequently, a solution of 40 g (0.1 mol) of l- (2'-chloro-4-biphenylyl) -2-chloro-l- (4-chlorophenyl) ethanol in 75 ml of dimethylformamide is added dropwise and 3 hours at 70 ⁰ C. heated. The reaction mixture is concentrated by distilling off the solvents in vacuo and the residue is stirred with water. The remaining crystals are washed with acetonitrile and recrystallized. This gives 16.2 g (40% of theory) of 1- (2'-chloro-4-biphenylyl) .l- (4-chlorophenyl) -2- (l, 2,4-triazol-1-yl) ethanol of Melting point 190 ^° C.

-Cl

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, analogous to Example 1, 75 g of 1- (2'-Chloro-4-biphenylyl) -2-c-chloro-1- (4-chlorophenyl) -ethanol.

Le A 19 636

2.2 1 140 - 28 -

- Cy ^C0CH 2 ^{cl cl}

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 293.7g (2.2 mol) of aluminum chloride are added in portions. After 18 hours, the reaction mixture is poured onto ice and hydrochloric acid. The organic phase is separated, washed, dried over sodium sulfate and concentrated in vacuo by distilling off the solvent. The remaining OeI is purified by distillation. This gives 478.7 g (90% of theory) of 4- (2-chlorophenyl) -phenacyl chloride of melting point 47 ° C.

 Analogously to Examples 1 to 5, the following compounds of the general formula '

R * _40)> - C - (CH ₂ ) _m -R (I)

to be obtained:

Le A 19 636

2T140 - 29 -

Ex.

No.

R ¹ R ² R ³ _n Az

Melting point (° C) or

refractive index

Cl-Cl-Cl-Cl

Cl

Cl) F

-ο

Cl

-b)

4-4-

.Cl 4- (Cl

4- <QVci H

Cl H

Cl H

A- /

/ = 1 N

X ι

\ ZZN

- -N

CI

H - -N

/ Ir-N

H - -N

-N-

-N ^N

-N-

/ -N

-N

ZRn

 r ·

H - -N

1 1 1 1

0 0 0 0 0

250 104 144

175

ng: 1.5992

160

189 217 144 164 170

160

220

Le A 19

Claims (3)

57 105 11 114 0 - 30 - Erfindunqsanspruch 1. Fungicidal agent, characterized by a content of at least one hydroxyalkyl-triazole of the general formula R ¹ C- (CH _o ) _m -R OH in which Az stands for triazolyl, R is optionally substituted phenyl, naphthyl or tetrahydronaphthyl, R is optionally substituted phenyl or cycloalkyl and R stands for 'hydrogen' or 2 R and R together in o-position to each other for an optionally substituted, multi-membered methylene bridge or together with the phenyl ring for naphthyl, R is halogen, alkyl, alkoxy or halogen ,. alkyl, η is O, 1, 2 or 3 and m is 0 or 1. 57 105 11 22 1140 or their physiologically acceptable acid addition salts, in addition to extenders and / or surface-active agents. 2. A method for combating fungi, characterized in that is allowed to act on fungi or their habitat hydroxyalkyl triazoles of the formula I. 3. Use of hydroxyalkyl-triazoles of the formula I, characterized in that for the control it from
Mushrooms are used.