CH638501A5 - 2,4-Dichlorophenyltriazolylethan-ones (-ols), fungicides containing these compounds, and processes for preparing the new compounds - Google Patents

Description

The present invention relates to new 2,4-dichlorophenyltri-azolylethanols (ols), fungicidal compositions which contain these compounds and processes for the preparation of the new compounds.

It has already become known that, in particular, 3,3-dimethyl-1-phenoxy-1-triazolylbutan-2-one and ole have good fungicidal activity (cf. German Offenlegungsschriften Nos. 2201063 [Le A 14118] and 2324010 [Le A 14971]). However, their effect is not always entirely satisfactory, especially when low amounts and concentrations are applied.

It was found that the new 2,4-dichlorophenyltriazolylethanols (-ols) of the general formula

Cl \

- 0 - CH - A -

(I)

- Cl

N "

fi.

il in which

A represents a keto group or a CH (OH) grouping, X represents halogen, alkyl or optionally substituted phenyl, and n represents integers from 0 to 3,

and their salts have strong fungicidal properties.

Fungicidal compositions are characterized in that they contain at least one compound of the formula I or physiologically tolerable salts thereof as the active ingredient component.

Those compounds of formula I in which A represents the CH (OH) group have two asymmetric carbon atoms; they can therefore exist in the two geometric isomers (erythro and threo form), which can be obtained in different proportions. In both cases they exist as optical isomers. All isomers are claimed according to the invention.

3rd

638 501

New 2,4-dichlorophenyltriazolyläthanone of the general formula

Cl

Cls

Cl-

- 0 -

(IA)

<0> -O-fH-CO-0

Br

-Cl

- Cl

NH

base

/

"N

-HBr

Clin which

A 'represents a keto group,

X represents halogen, alkyl or optionally substituted phenyl, and n represents integers from 0 to 3,

and their salts are prepared according to the invention by using 1-bromo-2- (2,4-dichlorophenyl) -l-phenoxyethane-2-one of the formula

-Cl

Cl

- 0 - CH - CO -

(II) - Cl

Cl.

O-CH-CO-

n y

If you use e.g. 1- (4-chlorophenoxy) -2- (2,4-dichlorophenyl) -1- (1,2,4-triazole-l-yl) ethane-2-one and sodium borohydride as starting materials, the reaction can be carried out by the following Formula scheme are reproduced:

Cls

Cl-

Br in which

X and n have the meaning given above, reacted with 1,2,4-triazole in the presence of a diluent and an acid binder and, if appropriate, converted compounds obtained by reaction with acids into the corresponding salts.

The new 2,4-dichlorophenyltriazolylethanols of the general formula

\

25th

-O-CH-CO

rfH

N Ü

-Cl

+ NaBH,

Cl-

-Cl

35

- 0 - CH - A -

(IB) - Cl

left

N

Ü

45

50

in which

A "represents a CH (OH) grouping,

X represents halogen, alkyl or optionally substituted phenyl, and n represents integers from 0 to 3,

and their salts are prepared according to the invention by first preparing, as described above, a compound of the formula IA and reducing it with complex borohydrides and converting the compounds obtained, if appropriate by reaction with acid, into the corresponding salts. The reduction is preferably carried out in the presence of a diluent.

Furthermore, the 2,4-dichloro-55 phenyltriazolylethane (-ols) obtainable according to the invention can be converted into the salts by reaction with acids.

Surprisingly, the active compounds according to the invention have a considerably higher fungicidal activity, in particular against cereal diseases, than the 3,3-dimethyl-l-phenoxy-l-triazolylbutan-2-one and ols known from the prior art, which compounds which are chemically and effectively related are. The active ingredients according to the invention thus represent an enrichment of technology.

If you use e.g. l-bromo-l- (4-chlorophenoxy) -2- (2,4-dichlorophenyl) ethane-2-one and 1,2,4-triazole as starting materials, the course of the reaction can be represented by the following formula:

60

The l-bromo-2- (2,4-dichlorophenyl) -l-phenoxyethane-2-one to be used as starting materials are generally defined by the formula II. In this formula, X preferably represents the halogens fluorine, chlorine, bromine and iodine, straight-chain or branched alkyl having 1 to 4 carbon atoms and phenyl optionally substituted by halogen, in particular chlorine. The index n preferably stands for integers from 0 to 2.

The following may be mentioned as starting materials of the formula II: -Brom-1-phenoxy-2- (2,4-dichlorophenyl) ethane-2-one -Brom-l- (4-chlorophenoxy) -2- (2,4-dichlorophenyl) ) ethanol-2-one-bromo-l (4-fiuorphenoxy) -2- (2,4-dichlorophenyl) ethanol-2-one-bromo-l- (4-bromophenoxy) -2- (2,4-dichlorophenyl) ethane-2-one-bromo-1 - (4-iodophenoxy) -2- (2,4-dichlorophenyl) ethane-2-one-bromo-1 - (2,4-dichlorophenoxy) -2- (2,4-dichlorophenyl) ethane-2-one-bromo-l - '(2,6-dichlorophenoxy) -2- (2,4-dichlorophenyl) ethane-2-one-bromo-l- (2,5-dichlorophenoxy) -2- (2nd , 4-dichlorophenyl) ethane-2-one-bromo-l- (3-fluorophenoxy) -2- (2,4-dichlorophenyl) ethane-2-one-bromo-l- (3-chlorophenoxy) -2- (2nd , 4-dichlorophenyl) ethanol-2-one-bromo-l- (3-bromophenoxy) -2- (2,4-dichlorophenyl) ethanol-2-one-bromo-l- (2-chlorophenoxy) -2- (2nd , 4-dichloi £ .henyl) ethane-2-one bromo-1 - (4-methylphenoxy) -2- (2,4-dichlorophenyl) ethane-2-one bromo-1 - (4-ethylphenoxy) -2 - (2,4-dichlorophenyl) ethane-2-one bromo-1 - (3-methylphenoxy) -2- (2,4-dichlorophenyl) ethane-2-one bromo-l- (2-methylphenoxy) - 2- (2,4-dichlorophenyl) ethane-2-one bromo-l- (2-isop ropylphenoxy) -2- (2,4-dichlorophenyl) ethanol-2-one -Brom-l- (4-chloro-2-methylphenoxy) -2- (2,4-dichlorophenyl) ethanol-2-one

-Brom-l- (4-bromo-2-methylphenoxy) -2- (2,4-dichlorophenyl) ethanol-2-one

-Brom-l- (4-fluoro-2-methylphenoxy) -2- (2,4-dichlorophenyl) ethane-2-n

-Brom-l- (4-iodo-2-methylphenoxy) -2- (2,4-dichlorophenyl) ethane-2-one -Brom-1 - (2,3-dimethylphenoxy) -2- (2,4-dichlorophenyl ) ethane-2-one-bromo-l- (4-biphenylyloxy) -2- (2,4-dichlorophenyl) ethane-2-one-bromo-l- (4-4'-chlorobiphenylyloxy) -2- (2, 4-dichlorophenyl) ethane-2-one

638 501

4th

1-bromo-l- (4-2 ', 4'-dichlorobiphenylyloxy) -2- (2,4-dichlorophenyl) ether -

2-on

1 -Brom-1 - (4-2,4'-dichlorophenylyloxy) -2- (2,4-dichlorophenyl) ethanol-2-one

1 -Brom-1 - (4-4'-bromobiphenylyloxy) -2- (2,4-dichlorophenyl) ethane-2-one l-bromo-l- (4-2-chlorobiphenylyloxy) -2- (2,4- dichlorophenyl) ethane-2-one The l-bromo-2- (2,4-dichlorophenyl) -l-phenoxyethane-2-ones of the formula II to be used as starting materials are not yet known, but can be prepared by known processes by e.g. known phenols of the formula

X.

n in which

X and n have the meaning given above, with a bromoacetophenone of the formula

Cl

\

implements. The remaining active hydrogen atom can then be exchanged for bromine in the usual way.

Suitable salts for the compounds of the formula I in fungicidal compositions are salts with physiologically tolerated acids. These preferably include the hydrohalic acids, e.g. hydrochloric acid and hydrobromic acid, especially hydrochloric acid, phosphoric acid, nitric acid, mono- and bifunctional carboxylic acids and hydroxy-carboxylic acids, e.g. Acetic acid, citric acid, sorbic acid, lactic acid, 1,5-naphthalenedisulfonic acid.

Inert organic solvents are preferably suitable as diluents for the reaction according to the invention. These preferably include ketones, such as diethyl ketone, in particular acetone and methyl ethyl ketone; Nitriles, such as propionitrile, especially acetonitrile; Alcohols, such as ethanol or isopropanol;

Ethers such as tetrahydrofuran or dioxane; aromatic hydrocarbons such as toluene and 1,3-dichlorobenzene, benzene; Form amides, such as especially dimethylformamide, and halogenated hydrocarbons, such as methylene chloride, carbon tetrachloride or chloroform.

The reaction is carried out in the presence of an acid binder. All commonly used inorganic or organic acid binders can be added, such as alkali carbonates, for example sodium carbonate, potassium carbonate and sodium bicarbonate, or such as lower tertiary alkylamines, cycloalkylamines or aralkylamines, for example triethylamine, N, N-dimethylcyclohexylamine, dicyclohexylmethylamine, NN-dimethyl benzylamine, further pyridine and diazabicyclooctane. An appropriate excess of triazole is preferably used.

The reaction temperatures can be varied over a wide range. Generally one works between about 0 to about 150 ° C, preferably at 60 to 120 ° C, in the presence of a solvent such as acetone or methyl ethyl ketone.

When carrying out the process according to the invention, 1 to 2 mol of azole and 1 to 2 mol of acid binder are preferably employed per 1 mol of the compounds of the formula II. To isolate the compounds of the formula I, the solvent is generally distilled off, the residue is taken up in an organic solvent and washed with water. The organic phase can be dried over sodium sulfate and freed from the solvent in vacuo. The residue is e.g. purified by distillation or recrystallization.

For a preferred embodiment of the reduction according to the invention, polar organic solvents are suitable as diluents for the reaction according to the invention. These preferably include alcohols, such as methanol, ethanol, butanol, isopropanol, and ethers, such as diethyl ether or tetrahydrofuran. The reaction is generally carried out at 0 to 30 ° C, preferably at 0 to 20 ° C. To do this, e.g. to 1 mol of the compound of formula II about 1 mol of a borohydride, such as sodium borohydride or lithium borohydride. For the preferred isolation of the compounds of formula I the residue is e.g. taken up in dilute hydrochloric acid, then made alkaline and extracted with an organic solvent, or only mixed with water and extracted with an organic solvent. Further processing can be carried out in the usual way.

In addition to the preparation examples and the examples in Table 1, the following may be mentioned as examples of particularly effective representatives of the active compounds according to the invention: 1 - (2-chlorophenoxy) -2- (2,4-dichlorophenyl) -1 - (1,2,4-triazoles -1 -yl) -ethane-2-one or -ol

1 - (2-isopropylphenoxy) -2- (2,4-dichlorophenyl) -1 - (1,2,4-triazol-1-yl) -ethane-2-one or -ol

1 - (2-Methylphenoxy) -2- (2,4-dichlorophenyl) -1 - (1,2,4-triazol-1-yl) -ethane-2-one or -ol

1 - (2-Chloro-4-methylphenoxy) -2- (2,4-dichlorophenyl) -1 - (1,2,4-triazol-l-yl) ethanol-2-one or -ol

The active substances according to the invention have a strong fungitoxic effect. They do not damage crops in the concentrations necessary to control fungi. For these reasons, they are suitable for use as crop protection agents for combating fungi. Fungitoxic agents in crop protection are used to control Plasmodiophoromy-cetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes.

The active compounds according to the invention have a broad spectrum of activity and can be used against parasitic fungi which attack above-ground parts of plants or attack the plants from the ground, and against seed-borne pathogens. They are particularly effective against parasitic fungi on above-ground parts of plants.

The active compounds according to the invention can be used with particularly good success as crop protection agents for controlling powdery mildew fungi, for example for controlling cucumber mildew (Ery-siphe cichoriacearum), powdery mildew (Podosphaera leucotricha) and powdery mildew as well as against other cereal diseases, for example grain rust.

The active compounds according to the invention can be used as crop protection agents for treating seeds or soil and for treating above-ground parts of plants.

The active compounds according to the invention can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, pastes and granules. These are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, e.g. organic solvents can also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, benzene or alkyl naphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylene or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. Petroleum fractions, alcohols, such as butanol or glyco, 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; with liquefied gaseous extenders or carrier

5

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15

20th

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30th

35

40

45

50

55

60

65

5

638 501

In the case of seed treatment, amounts of active compound of 0.001 to 50 g / kg of seed, preferably 0.01 to 10 g, are generally required.

For soil treatment, amounts of active ingredient of 1 to 1000 g / cm 3 of soil, in particular 10 to 200 g, are preferably required.

The versatile examples are shown in the following examples.

Example A

Shoot treatment test / powdery mildew / protective (leaf-destroying mycosis)

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

To test for protective activity, the single-leafed barley young plants of the Amsel variety are sprayed with the preparation of active compound as dewy. After docking, the barley plants are dusted with spores from Erysiphe graminis var. Hordei.

After 6 d residence time of the plants at a temperature of 21-22 ° C. and an air humidity of 80-90%, the stocking of the plants with mildew pustules is evaluated. The degree of infestation is expressed as a percentage of the infestation of the untreated control plants. 0% means no infection and 100% the same degree of infection as in the untreated control. The lower the mildew infestation, the more effective the active ingredient.

Active substances, active substance concentrations in the spray mixture and degrees of infestation are shown in the table below.

Table A

Shoot treatment test / powdery mildew / protective

Active ingredients

Active substance concentration in the spray mixture (% by weight)

Infestation (%) of the untreated control untreated

-

100

cl-0-0-o- <rH-c ° -c <CH3 h

N U

(known)

0.025

*

55.0

Cl - ^ - CO-ljiH-O-Q-Cl rf ^ N

(2) N U x HCl

0.025

0.0

Cl Cl d-O-00-? 11-0 - ^ - 01

r ^>

(4) N U x HCl

0.025

0.0

Substances are those liquids which are gaseous at normal temperature and pressure, e.g. Aerosol propellants, such as dichlorodifluoromethane or trichlorofluoromethane; as solid carriers: natural rock flour, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or s

Diatomaceous earth and synthetic rock powder, such as highly disperse silica, aluminum oxide and silicates: as emulsifiers; non-ionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl poly-glycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and io

Protein hydrolyzates; as a dispersant: e.g. Lignin, sulfite liquor and methyl cellulose.

The active compounds according to the invention can be present in the formulations in a mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, herbicides, bird repellants, growth agents, plant nutrients and agents which improve soil structure.

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

The active compounds can be used as such, in the form of their formulations 20 or the use forms prepared therefrom by further dilution, such as ready-to-use solutions, emulsions, suspensions, powders, pastes and granules. They are used in the usual way, e.g. by pouring, spraying, spraying, dusting, scattering, dry pickling, wet pickling, wet pickling, 25

Slurry pickling or incrustation.

When used as leaf fungicides, the active compound concentrations in the use forms can be varied within a substantial range. They are generally between 0.1 and 0.00001, preferably between 0.05 and 0.0001% by weight. 30th

638 501

Table A (continued) Sprout Treatment Test / Powdery Mildew / Protective

Active ingredients

Active substance concentration in the spray mixture (% by weight)

Infestation (%) of the untreated control

CI - ^ - CO-ÇH-O-QhQ-CI

rfNxN

(6) N LJ X HCl

0.025

16.3

/ C1

ci ^ Q-çh-çh-o- <Q> -ci

(3) NM x HCl

0.025

7.5

Cl Cl (14) ïï II X HCl

0.025

0.0

/ Cl

Cl ^ -fH-ÇH-O-Q-0

ohA

(15) N II X HCl

0.025

37.5

CI-C ^ -ÇH-ÇH-OhQ-kQ-CI 0iJ-N-

f | N (lé) N u

0.025

37.5

Example B

Shoot treatment testl cereal rust / protective (leaf-destroying mycosis)

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

To test for protective activity, single-leafed wheat young plants of the Michigan Amber variety are inoculated with a uredospore suspension of Puccinia recondita in 0.1% water.

seragar. After the spore suspension has dried on, the wheat plants are sprayed with the preparation of active compound and placed in a greenhouse for incubation for 24 h at about 20 ° C. and 100% atmospheric humidity.

After 10 d residence time of the plants at a temperature of 20 ° C. and an air humidity of 80-90%, the stocking of the plants with rust pustules is evaluated. The degree of contamination is expressed as a percentage of the infection of the untreated control plants. 0% means no infection and 100% the same degree of infection as in the untreated control. The less active the rust, the more effective the active ingredient.

Active substances, active substance concentrations in the spray mixture and degrees of infestation are shown in the table below.

60

65

7 638 501

Table B

Sprout treatment test / grain rust / protective

Active ingredients

Active substance concentration in the spray mixture (% by weight)

Infestation (%) of the untreated control untreated

-

100

<Q- <Q-0-CH-C0-C (CH3) 3 if JN

Ni II x HCl

(known)

0.025

33.8

Cl OH Cl - ^ - 0-CH-CH-C (CH3) 3

fit

(known)

0.025

33.8

Cl

Cl- CO-CH-0- <Q> -Cl ffSr

(2) N II x HCl

0.025

12.5

Cl-0-CO-ÇH-O ^ -O (f ^ N

(5) N II x HCl

0.025

10.0

Example C

Podosphaera touch (apple) / protective

Solvent: 4.7 parts by weight of acetone emulsifier: 0.3 part by weight of alkylaryl polyglycol ether water: 95 parts by weight

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

The spray liquid is used to spray young apple seedlings that are in the 4- to 6-leaf stage until they drip wet. The plants remain in the greenhouse at 20 ° C. and a relative atmospheric humidity of 70% for 24 h. They are then inoculated by dusting them with conidia of the powdery mildew pathogen (Podosphaera leuco-tricha) and placed in a greenhouse at a temperature of 21 to 23 ° C and a relative humidity of approx. 70%.

The infestation of the seedlings is determined 10 d after the inoculation. The rating values received are converted into percent infestation. 0% means no infection, 100% means that the plants are completely infected.

Active substances, active substance concentrations and results are shown in the table below.

(Table on the next page)

Example D

Erysiphe test (cucumber) / protective 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 for the desired active ingredient concentration in the spray liquid is mixed with the stated amount of solvent and the concentrate is diluted with the stated amount of water which contains the additives mentioned.

The spray liquid is used to spray young cucumber plants with about three leaves to the point of dripping wet. The cucumber plants remain in the greenhouse for drying for 24 hours. Then they are dusted with conidia of the fungus Erysiphe cichoriaceamm for inoculation. The plants are then placed in a greenhouse at 23 to 24 ° C. and a relative humidity of approx. 75%.

After 12 d, the infestation of the cucumber plants is determined. The rating values received are converted into percent infestation. 0% means no infection, 100% means that the plants are completely infected.

Active substances, active substance concentrations and results are shown in the table below.

50

55

60

638 501

8th

Table C Podosphaera-7esr (apple) jprotective

Active ingredients

Infestation (%) with an active ingredient concentration of

0.001

Cl- <Q> -0-CH-C0-C (CH3) 3

ffN ^ N 1 II

(known)

42

Cl cl-C ^ °° -ïH-0HQ> -cl

(2) N U x HCl

25th

Cl

Cl ^ -ÇH-Œ-O-0-Cl OH '

ff N

(3) N U x HCl

0

Cl C1N Cl- ^ ÇH-M-O-iQ-Cl

0H w

Ci

(14) N x HCl

0

Table D Erysiphe-Tayr (cucumber) / protective

Active ingredients

Infestation (%) with an active ingredient concentration of

0.00025

OH

Q ^ Q> -o-ch-ch-c (ch3) 5

fNil

N U

(known)

62

Table D (continued) Erysiphe-Tto (cucumber) / protective

Active ingredients

Infestation (%) with an active ingredient concentration of

, C1

Cl - @ - C0-CH-0 - @ - Cl ffN "N

(2) N U x HCl

12

Cl cl "Ö"? H "<rH" 0 "O ~ cl

0H N ^ 11

(3) n U x HCl

6

C1 C1V-.

ci ^ 0-çh-ch- ° -O-ci

0H N

if

(14) n U x HCl

16

, C1

Cl-O-CO-fH-O-O-O

(15) N U x HCl

12

Production Examples Example 1

Cl ci-0-o-ch-co- <Q> -ci so3h

N— ^ JL

x

S03H

To 149 g (2.13 mol) of 1,2,4-triazole in 1500 ml of acetonitrile, 244.6 g (0.62 mol) of l-bromo-l- (4-chlorophenoxy) -2- (2nd , 4-dichlorophenyl) ethane-2-one was added dropwise. The mixture is heated under reflux for 40 h. The solvent is then distilled off in vacuo, the residue taken up in 1000 ml of methylene chloride and with

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45

50

55

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65

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638 501

500 ml of water shaken out three times. The aqueous phase is shaken out again with 500 ml of methylene chloride. The combined methylene chloride phases are dried over sodium sulfate and concentrated by distilling off the solvent in vacuo. The residue is dissolved in 300 ml of acetone and mixed with 100 g of 1,5-naphthalene disulfonic acid hexahydrate in 200 ml of acetone. 270 g (41.3% of theory) of 1- (4-chlorophenoxy) -2- (2,4-dichlorophenyl) -1- (1,2,4-triazol-1-yl) ethane-2-one-naphthalenedisulfonate are obtained - (1.5) m.p. 198 ° C.

Example 2

Cl

\

Cl - (()) - 0-CH-C0

O

N U

■ Cl x HCl

From the l- (4-chlorophenoxy) -2- (2,4-dichlorophenyl) -l- (l, 2,4-triazol-l-yl) ethane-2-one-naphthalenedisulfonate- (1,5) the base is released by adding sodium bicarbonate solution, taken up in ethyl acetate and converted into the hydrochloride with ethereal hydrochloric acid, which crystallizes in ether after prolonged standing. Quantitatively l- (4-chlorophenoxy) -2- (2,4-dichlorophenyl) -l - (1,2,4-triazol-1-yl) ethane-2-one hydrochloride of mp 138-140 ° C. is obtained.

Example 3

Cl-

Cl

-0-CH-CH-1

X ° H

lu

-ci

"N

x HCl

226 g (0.42 mol) l- (4-chlorophenoxy) -2- (2,4-dichlorophenyl) -l- (l, 2,4-triazol-l-yl) ethanol-2-one-naphthalenedisulfonate- (l, 5) (Example 1) are slurried in 500 ml of methylene chloride, mixed with 1000 ml of saturated sodium bicarbonate solution and stirred for 5 hours. The isolated organic phase is dried over sodium sulfate and concentrated in vacuo. The residue is taken up in 1.51 methanol, 17 g (0.45 mol) sodium borohydride are added in portions of approx. 1 g at approx. 0 to 5 ° C. and the mixture is stirred for 15 h at room temperature. Then 200 ml of concentrated hydrochloric acid are added dropwise at 0 ° C. and the mixture is stirred again at room temperature for 15 h. The reaction mixture is then stirred into 1000 ml of saturated sodium bicarbonate solution, the aqueous phase is extracted with two 500 ml of methylene chloride and the organic phase with two 200 ml of water. The combined organic phases are dried over sodium sulfate and concentrated by distilling off the solvent in vacuo. The remaining oil is dissolved in 800 ml of ether and an excess of dry hydrogen chloride is added. 113.5 g (64% of theory) of 1- (4-chlorophenoxy) -2- (2,4-dichlorophenyl) -1 - (1,2,4-triazol-l-yl) ethanol-2-ol hydrochloride are obtained as a mixture of isomers of mp. 157-112 ° C.

The following compounds of Table 1 are obtained analogously to the examples mentioned above.

Table 1

Cl \

- 0 - CH - A -

- Cl n

N

N

N

Example No.

x "

A

Mp (° C)

4th

2,4-Cl2

CO

173-183 (x HCl)

5

4 <0>

CO

205-208 (x HCl)

6

0

A

O

Y

co

138 (dec.) (X HCl)

7

4-F

co

83-86

8th

2,6-Cl2

co

176 (x HCl)

9

3-C1

co

140-142 (x HCl)

10th

-

co

86-88

11

4-CH3

co

172 (x HCl)

12

4-C1, 2-CH3

co

138 (x HCl)

13

4-y

co

156 (x HCl)

14

2,4-Cl2

CH (OH)

68-85 (x HCl), mixture of isomers

15

4 <2>

CH (OH)

148-150 (x HCl), mixture of isomers

16

4V0VCI

CH (OH)

170-174 (x HCl), mixture of isomers

17th

4-F

CH (OH)

139-143 (x HCl), mixture of isomers

18th

-

CH (OH)

171-173 (x HCl), mixture of isomers

19th

3-C1

CH (OH)

155-158 (x HCl), mixture of isomers

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Claims (5)

638 501 PATENT CLAIMS 1. 2,4-dichlorophenyltriazolylethanol (ole) of the general formula Cl Y - 0 - CH - A - l 11 B in which A represents a keto group or a CH (OH) grouping, X represents halogen, alkyl or optionally substituted phenyl, and n represents integers from 0 to 3, and their salts. 2. Fungicidal composition, characterized in that it contains at least one new compound of the formula as active ingredient Cl \ (I) - Cl is also converted into the corresponding salts by reaction with acids. 4. Process for the preparation of new 2,4-dichlorophenyl-triazolylethanols of the general formula 0 - CH - A I (IB) - Cl • N- "N in which A represents a keto group or a CH (OH) grouping, X represents halogen, alkyl or optionally substituted phenyl, and n represents integers from 0 to 3, or contains their physiologically acceptable salts as the active component. 3. Process for the preparation of new 2,4-dichlorophenyl-triazolylethanolones of the general formula Cl \ - 0 - CH - A - if " (IA) - ci45 *1. N !1 in which A 'represents a keto group, X represents halogen, alkyl or optionally substituted phenyl, and n represents integers from 0 to 3, and their salts, characterized in that l-bromo-2- (2,4-dichlorophenyl) -l-phenoxyethane-2-one of the formula (II) - Cl in which X and n have the meaning given above, reacted with 1,2,4-triazole in the presence of a diluent and an acid binder, and compounds obtained were 65 d 0 15 in which A "stands for a -CH (OH) grouping, X represents halogen, alkyl or optionally substituted phenyl, and n represents integers from 0 to 3, 20 and their salts, characterized in that a compound of the formula (IA) is prepared by the process according to claim 3 and this is reduced with complex borohydrides and the compounds obtained are converted into the corresponding salts, if appropriate by reaction with acid. 25 5. The method according to claim 4, characterized in that one carries out the reduction in the presence of a diluent. 30th