DD152046A5 - FUNGICIDAL AGENT - Google Patents

Abstract

The invention relates to fungicidal compositions containing novel 1- (2,4-dichlorophenyl) -1- (2,6-dihalobenzylmercapto) -2- (1,2,4-triazol-1-yl) -ethanes of the general formula I. in which X and Y are the same or different and are halogen, as active ingredients. These agents are suitable for use as pesticides and can be used to combat powdery mildews, such as the causative agent of cucumber powdery mildew (Erysiphe cichoracearum) and real apple powdery mildew, with particular success.

Description

Fungicidal agent

The present invention relates to antifungal agents, the new l- (2,4-dichlorophenyl) ~ l ~ (2 ~ 6 _f dihalogenbenzylmercapto) -2- (l, 2, 4 ~ triazol-l-yl) ethanes as active ingredients "

Characteristic of the known technical solutions

It has already been disclosed that certain substituted l ~ benzylmercapto-l-phenyl-2- (I _f 2 _# 4 ° triazol-l ~ al) ethanes, such as l - (. 2,4-dichlorophenyl) '- l ~ (2 _{(4-dichlorbenzylmercapto)} ~ 2- (i _t 2 ₍₄ »triazol-l-yl) ~ ethane, good fungicidal properties (see U.S. Patent application Serial ftr * 8 * 33 926 of 16" 9 _e 1977 and German Offenlegungsschrift No. 2,724,684), but their effect is not always completely satisfactory in certain indication areas, in particular at low application rates and concentrations

ZieJ. of the invention

It has been found that the new 1 - (2,4-dichlorophenyl) -1- (2,6-dihalobenzylmercapto) -2- (l, 2,4-triazol-1-yl) ethanes have potent fungicidal properties "surprisingly, the compounds of the invention exhibit a considerably higher activity than the known from the prior art l- (2. '4 ~ dichlorophenyl)« l> - (2 _f 4 »° dichlorbenzylmercapto)" 2- (l _i 2 _t 4 ~ triazole ~ l-yl) ethane, which is the most obvious chemical and functional compound "The substances according to the invention thus represent an enrichment of the art",

- 2 -

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~ 2

statement

Essence of the invention

E3 were new _! (2,4-dichlorophenyl) -1- (2,6-dihalobenzylmercapto) -2- (l, 2,4-tria2ol-1-yl) -ethanes of the general formula

in which ·

X and Y are the same or different and are halogen,

and their physiologically acceptable acid addition salts found «

It has furthermore been found that the 1- (2,4-dichlorophenyl) -1- (2,6-dihalobenzylmercapto) -2- (1,2,4-triazol-1-yl) ethanes of the formula (I) is obtained , if

a) 1- (2- _i- 4-dichlorophenyl) -l-halo-2 "(l, 2,4-triazol-1-yl) -ethanes of the formula

CH - CH ₀ -

shark

VJ

(II)

in which

Shark stands for halogen,

with mercaptans of the formula

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HS-CH ₂ -. (Ο) ♦ ^(ΙΙΙ)

I ι ·

in which

X and Y are as defined above,

if appropriate in the presence of a diluent and an acid binder, the mercaptans of the formula (III) preferably being used in situ, or

b) 1- (2,4-dichlorophenyl) -2- (i, 2,4-triazol-1-yl) -1-thiol of the formula

-CH-CH ₀ -HI (IV)

with 2j6-dihalobenzyl derivatives of the formula

Z - CH ₂

in which

X and Y have the abovementioned meaning and

Z for halogen and the groupings

-O-SO ₅ -R ¹ and -N (R ² ) ^ ⁺ * , where

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1 R is alkyl or optionally substituted phenyl and

R is alkyl,

in the presence of a diluent and in the presence of a base.

If appropriate, an acid can subsequently be added to the compounds of the formula (I) thus obtained.

The 1- (2,4-dichlorophenyl) -1- (2,6-dihalobenzylmercapto) -2- (1, 2,4-triazol-1-yl) -ethanes according to the invention are generally defined by the formula (I). In this formula, X and Y are the same or different and are preferably chlorine or fluorine. Examples for compounds of formula (I) include: l- (2 _# 4-dichlorophenyl) - - (2,6-dichlorbenzylmercapto) "2- (1,2,4-triazoll ~ yl) ethane, 1! (2,4-dichlorophenyl) -I- (2-chloro-6-fluorobenzylmercapto) -2- (1,2,4-triazol-1-yl) ethane and 1- (2,4- Dichlorophenyl) -1- ( _2f 6-difluorobenzylmercapto) -2- (1 _l 2,4-triazole-1-yl) -ethane and its salts.

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If, for example, 1-chloro-i (2,4-dicihlorophenyl) -2- (i _t 2,4-triazol-1-yl) ethane and ^, G-dichlorobenzylmercaptan are used as starting materials, the course of the reaction can be described by the following equation be reproduced (method

a) i »* ''

pi . N

Cl

-CH-CH I Cl

-N

-I = J

H-S-CH

+ Base

HCl

Cl

Cl -

For example, using 1-chloro-1- ( _2f 4-dichlorophenyl) -2- (i, 2,4-tria2ol-1-yl) -ethane, Sje-dichlorobenzylchlorld and thiourea as starting materials, the reaction sequence may be as follows Formula scheme reproduced (method (a) without isolation of the intermediate):

Cl s

Cl

Cl -

^ z J

+ Cl-CH

Cl

- NaOH

C1 ~ -

Cl

CH-CHo-N. ²

-V- NaCl

Cl

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If, for example, 1- (2,4-dichlorophenyl) -2- (i, 2,4-triazol-1-yl) ethane-1-thiol and 2,6-dichlorobenzyl chloride are used as starting materials, the course of the reaction can be characterized by the following Formula scheme are reproduced (method b) i

he

base

The 1- (2 ₍ 4-dichlorophenyl) -1-halo-2- (1,2,4-triazol-1-yl) -ethanes to be used as starting materials in carrying out the process (a) according to the invention are represented by the formula (II) generally defined In this formula, Hal _- preferably chlorine or bromine.

The 1- (2,4-dichlorophenyl) -1-halo-2 - (1,2,4-triazol-1-yl) -ethanes of the formula (II) are known (compare DB-OS 25 47 954 [LeA 16 75O |). They are obtained by reacting the corresponding known 1- (2,4-dichlorophenyl) -1-hydroxy-2- (i, 2,4-triazol-1-yl> ethane (cf. DE-OS 24 31 407 [Le A No. 15,735J) with a halogen-releasing agent, for example thionyl chloride, if appropriate in the presence of a diluent, such as, for example, chloroform, at temperatures between 20 and 100 ^° C.

The addition * for the process (a) as starting materials to be used mercaptans are generally defined by the formula (III). In this formula

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X and Y are preferably those which have already been mentioned in connection with the description of the substances of the formula (I) according to the invention as being preferred for these substituents.

The mercaptans of the formula (III) are generally known compounds of organic chemistry and are obtained in a generally customary manner by reacting known 2 _f 6 -dihaloglybenzyl halides of the formula

Hal-CH ₂ - (O>, (VI)

in which

Hal, X and Y have the meaning given above »

With. Thiourea in the presence of a strong base, in particular sodium hydroxide solution, and in the presence of a solvent such as ethanol, heated. The resulting mercaptans can be reacted without isolation in a one-pot reaction directly with the compounds of formula (II) (see also the preparation examples.

The 1 ~ (2, ^z f -dichlorophenyl) -2- (1,2,4-triazol-1-yl) ethane-1-thiol of the formula (IV ) is described (see U.S. Patent Application Serial No. 833,926 of September 16, 1977 [Le A 17 456]); for preparation, see Preparation Examples.

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The 2,6-dihalobenzyl derivatives to be used as starting materials for the process (b) according to the invention are also generally defined by the formula (V). In this formula, X and Y are preferably those radicals which have already been mentioned in connection with the description of the compounds of the formula (I) preference, for these substituents. Z ₁ stands in front of preferably chlorine, bromine, iodine and the groups ^{1 2} (\ ¹

, -R ¹ and -N (R) o "t wherein R preferably is alkyl .." -, j having 1 to 4 carbon atoms or optionally by alkyl of .1 to 2 carbon atoms, chlorine, bromine, alkoxy having 1 to 2 carbon atoms, or nitro-substituted

2 is phenyl and R is preferably alkyl having 1 to 2 carbon atoms.

The 2,6-dihalobenzyl derivatives of the formula (V) are generally known compounds of organic chemistry.

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 as. As the hydrochloric acid and hydrobromic acid, especially the hydrochloric acid, further phosphoric acid, nitric acid, sulfuric acid, mono- and bifunctional carboxylic acids and hydroxycarboxylic acids, such as. As acetic acid, maleic acid, succinic acid, fumaric acid, tartaric acid, citric acid, sorbic acid, lactic acid, and sulfonic acid, such as. For example, p-toluenesulfonic acid and 1,5-naphthalenedisulfonic acid.

The salts of the compounds of formula (I) can be prepared in a simple manner by customary salt formation methods, for. By dissolving a compound of formula (I) in a suitable inert solvent and adding the acid, e.g. Hydrochloric acid, can be obtained and

, 57 684 11

known manner, ζ * example by filtration, isolated and g 'e ~ if appropriate purified by washing with an inert organic solvent v / ground.

For the erfindüngsgemäße implementation according to method (a) are suitable as diluents preferably inert organic solvents or aprotic solvents, "These include preferably ketones, such as diethyl ketones * in particular ^ acetone and methyl ethyl ketone, alcohols, such as ethanol or isopropanol, nitriles, such as propionitrile, in particular acetonitrile, hydrocarbons, such as ligroin, petroleum ether, benzene, toluene, xylene, and formamides, in particular dimethylformamide.

The reaction according to the invention in process (a) is carried out in the presence of an acid binder. It is possible to add all customary inorganic or organic acid binders, such as alkali metal carbonates, for example sodium carbonate, potassium carbonate and sodium bicarbonate, or lower tertiary allylamines, cycloalkylamines or aralkylamines, for example triethylamine, di-ethylbenzylamine or dimethylcyclohexylamine, or pyridine and diazabicyclooctane, and alkali metal alkoxides, for example, sodium methylate, potassium ethylate, or alkali metal hydroxides, for example, sodium hydroxide and potassium hydroxide.

The reaction temperatures can be varied within a substantial range when carrying out the process (a). Generally carried out between ⁰ · 20 and 150 C, preferably at the boiling point of the solvent, for example between 60 and 100 ⁰ C.

In carrying out the process (a) according to the invention, the amount used is 1 mol of the compounds of the formula (II)

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Preferably, about 1 to 2 moles of the mercaptan of formula (III) and about 1.5 to 2.5 moles of acid binder are used to isolate the compounds of formula (I), the reaction mixture is filtered, the filtrate is concentrated and the residue is washed with The mixture is then extracted by shaking with an organic solvent and the reaction product is isolated in a customary manner. The reaction products can optionally be purified by recrystallization.

In the preferred implementation of process (a) according to the invention, the reaction is carried out in a one-pot reaction ', d, h. without isolation of the mercaptans of formula (III). 1.2 moles of benzyl halide of the formula (IV), 1.2 to 2 moles of thiourea and 2 are preferably used per mole of the compounds of the formula (II) _; to 3 moles of base. The isolation of the compounds of the formula (I) is carried out in the usual manner.

For the reaction according to the invention in process (b), suitable diluents are protic and aprotic solvents, in particular those in which SLjI and Sjr 2 reactions are carried out. These include, for example, water, alcohols, carboxylic acids, acetone, acetonitrile, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetramethylurea or aromatic hydrocarbons, such as toluene.

Die.erfindungsgemäße reaction according to method (b) is carried out in the presence of a base. These include all commonly used organic and especially inorganic bases, such as sodium and potassium hydroxide or sodium and potassium carbonate.

- · Ί 1-

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The reaction temperatures can be varied within a substantial range when carrying out the process (b) according to the invention. In general, one works at. Temperatures between 20 and 1 ^ 0 C, preferably between 20 and 100 ⁰ C, or at the boiling temperature of the particular solvent.

In carrying out the process (b) according to the invention is preferably used for 1 mol of the compound of formula (IV) 1 to 3 moles of 2,6-dihalobenzyl derivative of the formula (V). To isolate the endpoints, the reaction mixture is freed of solvent and the residue is added with water and an organic solvent. The organic phase is separated and worked up in the usual way.

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

Fungicidal agents used in crop protection for the control of Plasmodiophoromycetes, Ooraycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes *

The good plant tolerance of the active ingredients in the concentrations necessary for the control of plant diseases permits treatment of above-ground parts of plants, of seedlings and of the soil.

As plant protection agents, the inventive

Active ingredients with particularly good success to combat

true powdery mildew, v / ie against the agent of the real

Cucumber powdery mildew (Erysiphe cichoracearura) and the real one

'. 57 684 11

Apple downy mildew (Podosphaera leucotricha), are used.

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, JB'einstverkapselungen in polymeric substances and in seed coatings, also in Formulations with burners, such as smoke cartridges, doses, spirals, and the like. Ä., And ULV KaIt and warm mist formulations.

These formulations are prepared in a known manner, for. Example, by mixing the active compounds with extenders, that is liquid solvents, liquefied gases under pressure and / or solid carriers, optionally with the use of surfactants, emulsifiers and / or dispersants and / or foam-forming agents. In the case of using water as an extender z. As well as organic solvents can be used as auxiliary solvent. 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, for. As 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 dimethylsulfoxide, as well as water; By liquefied gaseous diluents or carriers is meant those liquids which are gaseous at normal temperature and under normal pressure, e.g. B, aerosol propellant, such as halogenated hydrocarbons as well as butane, propane, nitrogen

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unt5 carbon dioxide; suitable solid carriers are: z, B, ground natural minerals, such as kaolins, clays, talc, circles, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates, as solid carriers for granules Questionnaire: B. Broken 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: for example, nonionic and anionic emulsifiers, such as polyaxylene-ferric acid esters, polyoxyethylene fatty alcohol ethers, eg. As alkylaryl polyglycol ether, alkyl sulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates; as dispersants in question: z. B ₄ lignin sulphite liquors and methyl cellulose.

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

Dyes, such as inorganic pigments, s. For example, iron oxide, titanium oxide, ferrocyan blue, and organic dyes such as alizarin, azole-Metallphthalocyaninfarbstoffe, 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 compound, preferably between 0.5 and 90% by weight

The active compounds according to the invention can be used in the formulated

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or mixtures thereof with other known active compounds, such as fungicides, bactericides, insecticides, carci- cides, 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 by the use thereof prepared by further dilution, such as ready-to-use solutions, emulsions, suspensions, powders, pastes and granules. The application is done in the usual way, for. By pouring, thawing, spraying, spraying, atomizing, vaporizing, injecting, silting, spreading, dusting, 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 0.0001 and 1% by weight, preferably _t between 0.001 and 0.5% by weight.

In the seed treatment, in general, amounts of active ingredient of 0.001 to 50 g per kilogram of seed, preferably from 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% by weight, are required at the site of action.

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Example A.

Erysiphe test (cucumbers) / Prothivorous

Solvent: 4.7 parts by weight of acetone

Emulsifier: 0.3 part by weight of alkylaryl poly

«Glycol ether

Water: 95.0 parts by weight, '-,

The amount of active substance necessary for the desired active substance 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 containing the additives mentioned.

Splash cucumber plants with about three leaves to dripping wet. The cucumber plants remain in the greenhouse for 24 hours to dry them. Then they are pollinated with conidia of the fungus Erysiphe cichoracearum 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 hours, the infestation of cucumber plants is determined. The obtained rating values are converted into percent infestation. 0 % means no infestation, 100% means that the plants are completely infested «

 Active ingredients j active ingredient concentration and results are shown in the table below.

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Table A

Erysiphe Test (cucumbers) / Protective

Active ingredient infestation in% at an active substance concentration of 0.0005 %

/ Cl I

° 1- (&> -CH-CH ^ -N

"N

Cl

(known)

⁰¹ -

- CH-CH,

S Cl

CH ₂

"" XI

CI

(D

x2 ENT.

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Example B

Podosphaera test (apple) / protective

Solvent: 4.7 parts by weight of acetone

Emulsifier: 0 * 3 parts by weight Alkylarylpolyglykolether

V / asser ·: 95 »O G-shares

The amount of active substance necessary for the desired active substance concentration in the spraying liquid is mixed with the stated amount of the solvent and the concentrate is diluted with the indicated 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 "plant * remain 24 hours at 20 ⁰ C and a relative Lirftf euchtigkeit of 70% in the greenhouse. Then, they are inoculated and placed in a greenhouse with a temperature of 21 to 23 ⁰ C by dusting with conidia of the apple powdery mildew causative organism (Podosphaera leucotricha) 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.

Drugs, drug concentrations and results are shown in the table below:

Table B

Podosphaera test / protective

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Active ingredient infestation in% at an active substance concentration of 0.0001%

Cl Cl - (Ο) - CH-CH,

Cl '

(known)

MO.

Cl

Cl

Cl

/ Cl

H 2 ENT,

(1)

16

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Production Examples Example 1

Cl -

- ch - CH ₂ - ν

606s (3.1 mol) of 2,6-dichlorobenzyl chloride are dissolved in 2.5 ethanol and added to 258 g (3.4 mol) of thiourea in 1000 ml of ethanol »is heated for 6 hours under stirrer and reflux, distilled 1.5 1 of ethanol Cools to 45 ⁰ C and drips under nitrogen atmosphere / 173.6 g (4.34 EoI) of sodium hydroxide, dissolved in 342 g of water, within 1.5 hours to "After completion of the addition is stirred for 30 minutes at 45 ⁰ C. , Subsequently, 600 g (2.1 mol) of 1-chloro-1- (2,4-dichlorophenyl) "2- (1,2,4-triazol-1-yl) -ethane in 2 1 of ethanol are added dropwise within 3 hours. The mixture is stirred for 15 hours at 40 ⁰ C, distilled 1 _f 5 1 of ethanol at 50 ⁰ C in vacuo, allowed to cool and mixed with 4 1 of water. The reaction mixture is extracted once with 4 l and three times with 2 l each of methyl chloride; the combined methylene chloride phases are washed twice with 2 l of water each time, dried over sodium sulphate and concentrated by distilling off the solvent in a water-jet vacuum. The oily residue is dissolved in 2.5 l of ethanol and 38 g of 1,5-naphthalenedisulfonic acid in 2 l of ethanol are added. The resulting precipitate is filtered off with suction and carefully stirred into 3 l of sodium bicarbonate solution. The free base is extracted with 18 l of methylene chloride, the organic phase is distilled off by distillation

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Concentrated methylene chloride, the residue dissolved in 3 1 chloroform and treated dropwise with 66 ml (1.53 mol) of 96% nitric acid with Eixkühlung. 1000 ml of diethyl ether are then added, the resulting precipitate is filtered off with suction and washed with 500 ml of diethyl ether. This gives 661 g (61.3 % of theory) of 1- (2,4-dichlorophenyl) -1- (2,6-dichlorobenzylmercapto) -2- (1,2,4-triazol-1-yl) ethane nitrate with a melting point of 156 to 158 ⁰ C.

The above compound can also be prepared by reacting 1 ~ (2- _t 4-dichlorophenyl) -1-thiol-2- (1,2,4-triazol-1-yl) -ethane (see below for its preparation) and 2, 6-dichlorobenzyl chloride in the presence of a diluent (eg, ethanol or acetone) and a base (eg, potassium carbonate).

ι - ii ii νγ

Precursor: Cl - \ O / - CH - CH ₂ - NI

' ^N N: = J

^N N: = J χ HCl

16.05 g (0.05 mol) of 1-bromo-1- (2,4-dichlorophenyl) -2- (i, 2,4-triazol-1-yl) ethane and 4.2 g (0.055 mol) of thiourea are refluxed in 50 ml of methanol for 3 hours. The mixture is allowed to cool to 0 ⁰ C and added dropwise under nitrogen atmosphere within 30 minutes 25 ml of 2N sodium hydroxide solution. Then allowed to stir for 2 hours at room temperature, 100 ml of water are added and extracted three times with 50 ml

Concentrated methylene chloride, the residue 'dissolved in 3 1 chloroform and'tropfenweise- with.66 ml (1.53 mol) of 96% nitric acid were added under ice cooling. 1000 ml of diethyl ether are then added, the resulting precipitate is filtered off with suction and washed with 500 ml of diethyl ether, Man, 661 g (61.3 % of theory) of 1- (2,4-dichlorophenyl) -1- (2,6-dichlorbenzylmercapto ) -2- (l, 2,4-triazol-1-yl) -ethane-nitrate of melting point 156-158 ° C.

The above compound can also be obtained by using 1- (2,4-dichlorophenyl) -1-thiol-2- (1,2,4-triazol-1-yl) -ethane (see below for preparation thereof) and 2, 6-dichlorobenzyl chloride in the presence of a diluent (eg ethanol or acetone) and a base (eg potassium carbonate).

Precursor: q ^

x HCl

16.05 g (0.05 mol) of 1-bromo-1- (2,4-dichlorophenyl) -2- (i, 2,4-triazol-1-yl) -ethane and 4.2 g (0.055 mol) Thiourea are refluxed in 50 ml of methanol for 3 hours, allowed to cool to ^{0 0} C and added dropwise under nitrogen atmosphere within 30 minutes 25 ml of 2 N sodium hydroxide to. Thereafter, it is allowed to stir at room temperature for 2 hours, 100 ml of water are added and the mixture is extracted three times with 50 ml each time

Le A 19 794

Methylene chloride. The combined organic phases are dried over sodium sulfate and treated with 30 ml of ethereal hydrochloric acid. This crystallized 13.8 g (37.6 % of theory) of 1- (2,4-dichlorophenyl) -2 ~ (1,2,4-triazol-1-yl) ethane-1-thiol hydrochloride of melting point 149th -5O ⁰ C off ..

The following compounds of the general formula

Cl

CH-CH ₀ -N

χ ²

can be obtained in a similar way:

Example no. X Y Physics. Properties 2 Cl F oil 3 F F Oil. A 'Cl Cl n ^ ° = 1.6158

Le A 19 794

Claims (3)

1. Fungicidal agent, characterized by a content of at least one l- (2,4-dichlorophenyl) -1- (2,6 »dihalobenzylmercapto) -2 ~ (l, 2,4-triazol ~ l» yl) ~ ethane of the formula I. (I) in which X and Y are the same or different and for * Halogen · stand, and their physiologically acceptable acid addition salts, in addition to extenders and / or surface-active agents » 2. A method for controlling fungi, characterized in that l- (2 _i 4 »dichlorophenyl) ~ l ~ (2,6-dihalobenzylmercapto) ~ 2- (l, 2,4 ~ triazol-l ~ yl)» ethane of formula I is allowed to act on fungi or their habitat * 3. Use of l- (2,4 <-Dichlorphenyl.) - l '- (2,6-dihalo ~ beri2ylrnercapto) »ethanes 2" (triazol "I, 2 _i 4 ~' l '-yl) of Formula "I, characterized by the fact that they are used to combat fungi" A process for the preparation of fungicidal agents is characterized by the use of i (2 _e 4-dichlorophenyl) -l (2,6-dihalobenzylmercapto) 2 - (, 1 _f 2 _f 4 <- triazal-1-yl ) -ethan8 Oer formula I with extenders. ·! and / or surface-active agents.