CS195340B2 - Fungicide and growth plant regulator and process for preparing effective compounds - Google Patents

Abstract

New (1-phenyl-2-triazolylethyl) thioethers and -thiols (mercaptans) of the general formula I' <IMAGE> in which the substituents are as defined in Claim 1, and salts thereof, are obtained by reacting 1-halo-1-phenyl-2-triazolylethane derivatives with thiols (mercaptans) or hydrogen sulphide and converting the resulting compounds, if appropriate, to the salts. The resulting compounds are, if appropriate, oxidised to give new sulphoxides and sulphones. The new compounds can be used as at least one active compound in fungicides and as plant growth regulators.

Description

The invention relates to novel (1-phenyl-2-triazolylethyl) thioethers, to a process for their preparation and to their use as fungicides and plant growth regulators.

It is already known that 1- [t-aryl- (3- (R-oxy) ethyl) imidazoles, such as 1- [t -butoxy-β- (4'-chlorophenyl) ethyl] imidazole, exhibit good fungicidal activity ( see DOS No. 2,063,857) In certain areas of indication, the effect of these compounds, especially when applied at lower levels and concentrations, is sometimes not entirely satisfactory.

It is further known that 2-chloroethylphosphonic acid exhibits plant growth regulator properties (see, for example, DOS No. 1667 968). However, the results obtained with this compound are not always satisfactory.

It has now been found that the novel (1-phenyl-2-triazolylethyl) thioethers of formula I,

punching a phenyl group or an optionally chlorinated phenoxy, n ₇ is an integer equal to 3 and Q.až.

R‘ represents a hydrogen atom, a methyl group, a phenyl group optionally substituted by chlorine and / or an alkyl of up to 4 carbon atoms, or represents an optionally chloro-substituted benzyl group, and their salts have potent fungicidal and plant-regulating properties.

It has further been found that the (1-phenyl-2-triazolylethyl) thioethers of the above general formula (I) are obtained by substituting 1-halo-1-phenyl-2-triazolylethanes of the general formula (II),

X (/// in which

Wounds have the meanings given above and

X represents a halogen atom and does not react with mercaptans of general formula III,

R‘ — S — H ’(Ш). in which in which

R represents a halogen atom or a halogen atom

As used herein, the term &quot; denoted &quot;, optionally in the presence of a diluent and an acid binding agent.

Surprisingly, the i- (phenyl-2-triazolylethyl) thioethers of the present invention exhibit appreciably higher fungicidal activity, in particular against various scabs and powdery mildew than prior art 1- [N-aryl- [3- (R-oxy)] known in the art. ethyl] imidazoles, for example 1- [t -butyl-β- (4'-chlorophenyl) ethyl] imidazole, which are chemically and efficiently the closest related substances. Ppdlb compounds. The invention thus represents an enrichment of the prior art.

It should be noted that the disclosed compounds show interesting effects on wading and plant growth suppression.

If 1-chloro-1- (2,4-dichlorophenyl) -2- (1,2,4-triazol-1-yl) ethane and 4-chlorothiophenol are used as starting materials, the reaction can be carried out according to of the invention to be described by the following reaction scheme:

The starting materials of the formula II are not yet known. These compounds can be prepared by the known 1-hydroxy-1-phenyl-2-triazolylethanes (cf. DOS No. 2,431,407) of the general formula IV, ^R and OH (IV) in which:

Ran is as defined above, reacted with halogen-introducing agents, for example thionyl chloride, optionally in the presence of a diluent, for example chloroform, at a temperature between 20 and 100 ° C (see also examples).

The starting materials of the general formula (III) are generally known compounds in organic chemistry.

Suitable salts of the compounds of the formula I are salts with physiologically compatible acids, which preferably include hydrohalic acids, such as hydrochloric and hydrobromic acids, phosphoric and nitric acids, and, in addition, mono- and dibasic carboxylic and hydroxycarboxylic acids, such as acetic acid. , maleic, succinic, fumaric, tartaric, citric, salicylic, sorbic and lactic as well as sulfonic acids such as 1,5-naphthalenedisulfonic acid.

Salts of the compounds of formula (I) may be prepared in a simple manner by conventional salt-preparation methods, for example by dissolving the base in an ether, for example ethyl ether, and adding an acid, for example hydrogen chloride, and can be isolated in a manner known per se, for example by filtration and optionally purified.

Suitable diluents for use in the process according to the invention are preferably inert organic solvents or aprotic solvents, which preferably include ketones, such as diethyl ketone and in particular acetone and methylethyl ketone, alcohols such as ethanol or isopropanol, nitriles, such as propionitrile and especially acetonitrile, hydrocarbons such as ligroin, petro, lethal benzene, toluene and xylene, as well as dimethylformamide.

The reaction according to the invention is carried out in the presence of an acid binding agent. All conventional inorganic or organic acid binding agents such as alkali metal carbonates, for example sodium carbonate, potassium carbonate and sodium bicarbonate, longer lower tertiary alkylamines, cycloalkyl amines or aralkylamines, for example triethylamine, dimethylbenzylamine or cyclohexylamine, pyridine, can be used for this purpose. , diazabicyclooctane, as well as alkali metal alkoxides such as sodium methoxide and potassium ethoxide, or alkali metal hydroxides.

metals such as sodium and potassium hydroxide. ..

The reaction temperatures were. they can move within wide limits. Generally they work ;; at a temperature between 20 ° C and 150 ° C, preferably at the boiling point of the solvent, for example at a temperature between 100 ° C and 100 ° C.

In the process according to the invention, the following: per mole of the compound of formula (II), preferably about 1 to 2: mole of mercaptan of the formula IH and roughly 1.5 to 2.5 are used. moles of acid binding agent. To isolate the compound of formula (I), the reaction mixture is filtered, the filtrate is evaporated, the residue is digested with aqueous base, the mixture is shaken with an organic solvent and the reaction product is then isolated in the usual manner. The reaction products may optionally be purified by recrystallization or distillation.

The active compounds according to the invention show a strong fungicidal action and the bacteria have a toxic action. The substances in concentrations necessary for combating fungi do not damage crop plants. For these reasons, they are suitable for use as agents for protecting plants against fungi and bacteria. Fungitoxic agents are used in plant protection for combating fungi of the classes Plasmo.diophoromycetes, Oomycetes, dysiophys, Zygomycetes, Ascomycetes, Basidiomycetes. and Deuteromyce.tes. .

The active compounds according to the invention have a very wide spectrum of activity and can be used against parasitic fungi and bacteria attacking the surface parts of plants, attacking plants from the soil, as well as against pathogens. transmissible seed diseases. .

Particularly good ^{effect, and} it m the compounds against parasitic fungi on above-ground parts of plants are j.ako Erysiphe species, Uromyces and Venturia, for example against the causative organism of cucumber powdery mildew (Erysiphe cichoracearum), powdery mildew jabloňového- (Podosphaera leucotrichaj and apple scab (Fuscladium It is particularly advantageous that the compounds according to the invention do not only have a protective effect, but are also curative, i.e. up to infection.

As plant protection agents, the compounds of the present invention can be used to treat soil, seed and aerial parts of plants.

The active substances used in the context of the invention interfere with the metabolism of plants and can therefore be used as growth regulators.

For. type of effect of plant growth regulators, according to experience to date, the active ingredient can act on the plants with one or several different effects. The effects of the substances depend essentially on the time of application, based on the developmental stage of the seed or plant, as well as on the amount of active substance applied to or in the vicinity of the plants and further on the mode of application. In any case, plant growth regulators should positively influence crop plants in a desirable manner.

Plant growth regulating substances can be used, for example, to suppress the vegetative growth of plants. Such growth suppression is of economic importance, inter alia, in grassland, since, by suppressing grass growth, for example, the frequency of mowing in ornamental gardens can be reduced. in parks and sports facilities or on the roadside. It is also important to suppress the growth of herbaceous and woody plants at roadside and near overhead lines or, in general, where strong growth is undesirable.

Also important is the use of plant growth regulators to suppress crop growth in grain, as this reduces or eliminates the risk of plants lying down before harvest due to crop shortening. In addition, plant growth regulators can act to strengthen the stalks of the grain, which also counteract the growth.

Suppression of vegetative. · allows for the growth of many crop plants denser planting possible, so that m _(Uze achieve an increase in revenue per unit · · surface.

Another mechanism for increasing yield by growth inhibitors is that nutrients are used more intensively for the formation of flowers and fruits, while vegetative growth is reduced.

By stimulating growth regulators, stimulation of vegetative growth can often be achieved. This is of considerable importance in cases where:. when the vegetative parts of the plants are harvested. However, stimulation of vegetative growth can also lead to stimulation of generative growth so that, for example, more fruits can be formed or larger fruits can be produced.

Increased yields can, in many cases, also be achieved by interfering with plant metabolism without any noticeable changes in vegetative growth. Growth regulators can further influence the changes in the composition of the plants in order to achieve a better quality of the harvested products. Thus, for example, it is possible to increase the sugar content of sugar beet. cane, pineapple, as well as citrus fruits, or increase the protein content in soy or grain.

Parthenocarpic (seedless) fruits may be produced by growth regulators. Furthermore, the sex regulators can influence the sex of the flowers.

Growth regulators can also positively influence the production or discharge of secondary plant substances. Examples include the stimulation of latex outflow in rubber trees.

During plant growth, the number of side shoots can be increased by the use of growth regulators due to chemical violation of apical dominance. This is important, for example, for the propagation of plants by rootstocks. However, it is also possible to suppress the growth of the side shoots, for example in the case of tobacco, where the development of the side shoots is prevented after decapitation and thus to promote leaf growth,

The effect of the active ingredients on the foliage of the plants can be controlled so that the plants can be completely de-leafed at the desired time. Such defoliation is important for facilitating mechanical harvesting, for example in wine or cotton, or for reducing transpiration during the period when plants are to be transplanted.

Due to growth regulators, premature fruit loss can be prevented. However, it is also possible to promote fruit decay, for example in the case of fruit, in the sense of a kind of "chemical thinning" to some extent. . Growth regulators can also serve to reduce crop plants. the power needed. at harvest time to break off the fruits so that mechanical harvesting or manual harvesting is facilitated.

Growth regulators can further accelerate or slow down the ripening of harvested products before or after harvesting. - - This is a fact. particularly advantageous, since. when used, it is possible to achieve optimal adaptation to market requirements. In addition, growth regulators - in many cases, serve to improve the coloring of fruits. In addition, growth regulators can achieve the concentration of fruit ripening within a certain period of time. This creates the preconditions for, for example, tobacco, tomato or coffee plants to be able to carry out fully mechanical or tannic harvesting in only one working stage.

The use of growth regulators can also affect seed-or bud-like resting periods, i.e. endogenous annual rhythm, so that plants, such as pineapples or ornamental plants in horticulture, germinate, sprout or do not bloom at a time when under normal conditions. - did not germinate, sprout, respectively. nekvetly.

By means of - growth regulators it is also possible to achieve delayed bud sprouting or delayed germination - by way of example, to prevent damage caused by autumn frosts in areas with colder climates.

Halophilia can also be achieved in crop plants with growth regulators. This will create the preconditions for growing plants on soils containing salts.

Growth regulators can - also - achieve higher resistance to frost and dryness in 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 compositions are prepared in a manner known per se, for example by mixing the active ingredient with fillers, i.e. liquid solvents, liquefied gases under pressure and / or solid carriers, optionally using surfactants, i.e. emulsifiers and / or dispersants. and / or foaming agents. If water is used as a filler, it is also possible, for example, to use organic solvents as a solvent. Basically suitable liquid solvents are: aromatics such as xylene, toluene, benzene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strong polar solvents such as dimethylformamide and dimethylsulfoxide, and water. By liquefied gaseous fillers or carriers is meant those liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants such as dichlorodifluoromethane or trichlorofluoromethane. Suitable solid carriers are: natural stone meal, such as kaolins, alumina, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and synthetic stone meal, such as highly dispersed acid, silicas, alumina and silicates. Suitable emulsifiers are non-ionic and anionic emulsifiers, such as polyoxyethylene esters of fatty acids, polyoxyethylene ethers of fatty alcohols, e.g.

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

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

The active compounds according to the invention can be applied as such, in the form of concentrates or - by further dilution thereof - ready-to-use dosage forms, such as ready-to-use solutions, emulsions, suspensions, powders, pastes and granules. Application is carried out in the usual manner, for example by watering, - spraying, dusting, tossing, pickling - dry, wet, wet or in suspension, or incrustation.

When using the active ingredients - as foliar fungicides - their concentrations in the formulations applied can vary within wide limits. These concentrations generally lie between 0.1 and 0.00001 wt. %, preferably between 0.05 and 0.0001 wt. %.

Based on the area of the soil to be treated, it is generally necessary to apply between 0.1 and 50 kg, preferably between 0.5 and 10 kg, of active compound per hectare.

When used in the appropriate amounts, the compounds of the invention also show insecticidal and acaricidal activity.

For - the period of use, the application,

The sieved compounds as growth regulators are carried out at a preferred time interval, the exact boundary of which is controlled by ‘climatic-

- me and vegetative conditions; -

The versatility of the compounds of the invention is illustrated by the following examples. 7 ’·. : »

Example A

Powdery mildew test (cucumbers) / protective action solvent: 4.7 parts by weight of acetone, emulsifier: 0.3 parts by weight of alkylaryl polyglycyl ether, water: 95.0 parts by weight.

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

Young cucumber plants having about 3 leaves are sprayed by liquid spray until dew. The plants are left to dry in a greenhouse for 24 hours, then inoculated by dusting with spores of Erysiphe cichoracearum (powdery mildew) and then stored in a greenhouse at 23-24 ° C and about 75% relative humidity.

After 12 days, the plants were found to be infected with smokers. The values obtained are converted to percent attack. 0% means no infestation, 100% means complete infestation of plants.

The active substances, the active substance concentrations and the results obtained are given in the following Table A.

Talulka A

Protective test for powdery mildew (Erysiphe) on cucumber degree of attack in% at the end of the active substance

xHNOy

Cl (I). · 7pf 0 ^: ···. ·· '·.

'effective test for apple powdery mildew' (Rodos'phaera). - ·· _ ..., · ...

solvent: 4.7 parts by weight of aceton, emulsifier:. 0.3. parts 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 is mixed with the indicated amount of solvent, and the concentrate is diluted with the specified amount of water containing the above ingredients.

^; By spraying, young apple seedlings having 4 to 6 leaves are sprayed until wet. and placed in a greenhouse having a temperature of 21 to 23 ° C and a relative air humidity of about 70 ° / o. Ten days after the inoculation, the infected seedlings were infected. The values obtained are converted to% attack.

% means no infection, 100 -% represents complete infestation of plants.

The active substances, the active substance concentrations as well as the results obtained are shown in Table B.

Table B

Protective test for apple mildew (Podosphaera) degree of attack in% at concentration · active substance active substance 0,0025% (2) (1)

Cl

Cl

19S34 О active substance

Degree of attack in% at the active compound concentration

0.0025%. T

Example G

Fusicladium scab test Solvent: 4.7 parts by weight of acetone, emulsifier: 0.3 parts by weight of alkyl aryl polyglycol ether, water: 95 parts by weight.

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

By spraying, the young apple seedlings in the 4-6 leaf stage are sprayed until dripping. The plants are kept for 24 hours in a greenhouse at 20 ° C and 70% relative humidity, then inoculated with an aqueous suspension of spores of Fusicladium dendritjicum (apple scab) and incubated for 18 hours in a humid chamber at 18-20 degrees Celsius and 100 ° C. % relative humidity.

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

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

% means no infestation, 100% means complete infestation of plants.

The active substances, active substance concentrations and results obtained are given in the following Table C.

T a b u 1 к a C

Protective test for apple scab (Fusicladiumi) active substance attack in% at active substance concentration 0,0025% 0 /) 01% attack in ·% at active substance concentration

0.0025% '0.001%

193340

Example D

Test for Erysiphe graminis var, hordel (fusariñzaj-treatment of shoots. Plants (leaf-destroying mycosis - 'protective and curative effect')

To prepare a suitable active ingredient, 0.25 parts by weight of the active ingredient are mixed in 25% by weight. parts of dimethylformamide and 0.06 parts by weight of alkylaryl polyglycol ether 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) at one leaf stage are sprayed until moistened with the active ingredient prepared. and dusts after drying. spores of fungi Erysiphe graminis var. hordei.

When Determining. The curative effect is similar, but in reverse order. In this case,. young barley plants in one leaf stage are treated with the active agent 48 hours after inoculation, when the infection is already obvious.

After six days when the plants were grown at 21-22 ° C and 80-96%. humidity, evaluate the extent of disease on plants. The degree of infestation is expressed as a percentage of the untreated control infestations. 0% means no infestation and 100% the same as untreated control plants. Tested. the more effective the lower the substance is. is the degree of attack.

Effective. the substances, the concentration of the active substances in the spraying and the degree of attack are shown in the following Table D.

Table D

Test for Erysiphe graminis (treatment of plant shoots) - protective and curative effect active substance concentration of the active substance in the spray (% by weight) infestation in% infestation of untreated control plants protective curative untreated

О c ^^ 1/2 (ojo) (лолтл)

100 100

0.0025 70.0 82.5

0.0025 3.8 0.0

0.0025 48.8 0.0

X HNO ₅ ci

0.0025 41.3 8.8 (3)

-0 4 -0

18

Example Ε

Braking. Soybean growth solvent: 10 parts by weight of methanol, emulsifier: 2 parts by weight of polyethylene sorbitan monolaurate.

To prepare a suitable active ingredient, 1 part by weight of the active ingredient is mixed with the indicated amount of solvent and. emulsifier and the mixture is made up to the desired concentration with water.

Young plants - soybeans - are sprayed with the active ® medium at the point at which they first unfolded the leaf. After 2 weeks, the increment is measured and the inhibition of growth in ° / o relative to the increment in control plants is calculated. 100% means growth arrest and 0% represents the same growth as untreated control plants.

The active substances, the active substance concentrations and the results obtained are. are shown in Table E below.

Table E active substance control

Soybean growth inhibition concentration of effective slackening-substance growth in%. in - '%

-. -. 0

CH 3 CH-CN * 1,. , Cl (zodma)

0.05

0,05 o

Cl — CH2 — CH2 —P (OH) 2 (known)

0,05 100

Example

Cotton growth inhibition solvent: 10 parts by weight of methanol emulsifier: 2 parts by weight of polyethylene sorbitan monolaurate ·

To prepare a suitable active ingredient, 1 part by weight of the active ingredient is mixed with the indicated amounts of solvent and emulsion, and the mixture is made up to the desired concentration with water.

Young 4-leaf cotton plants are sprayed with the active ingredient until dripping. At 3 weeks, the increment is measured and the growth inhibition in% relative to the increment in control plants is calculated. 100% means growth arrest, and - 0% represents the same growth as untreated control plants.

The active substances, active substance concentrations and results obtained are given in Table F below.

19O 4 O

Table F

It inhibits growth, which is effective in controlling the concentration of effective inhibition.

.................... i .....: Θ .........

0.05

The following examples illustrate the preparation of the active compounds according to the invention.

Example 1

Preparation of intermediate:

Cl

31.8 g (0.1. Pncd) of 1-chloro-1- (f-phloro-4-biphenylyl) -2 :-( 1,2,4, -triazol-1-yl) ethane together with 29 ξ (0.2 mol) of 4-chlorothiophenol and 29 g (0.2¾ mol) of potassium carbonate in 100 ml of acetone are heated at reflux for 6 hours. The ether fusion was dried with sodium sulfate and the solvent was evaporated, yielding 34.4 g (81% of theory) of l-chloro-phenyl-mercapto-1. - (4'-Chloro-4-biphenylyl) -2- (1,2,4-triazol-1-yl) -1H-p-point. mp 115 ° C. The product is dissolved in chloroform and 6 ml of 98% nitric acid are added to the solution, whereupon a crystalline material precipitates which, after recrystallization from isoppopanol, yields

38.2 g [80 '%' of theory] .1 -. (4-ο.οο-6Β} {111 $ 0) r- (4'-εύ) 9Ρ-4 .-- ύί ^ γ ^ 1) -2 - / l, ^{2,4-triazol-l:} -yljethannitrátu, tajícíhq decomposition 144 ° C

Dissolve 150 g g (0,5 mol) of 1- (4'-οωο; τ-4-Μ y j yl) -1) -1 hyd -hydroxy Ч 2 (1 _; 2,4 Ч 1 х о -1 -1 -1 -1 -1) l) - ethane in 2 liters of chloroform; The mixture is heated to boiling, and 90 g (0.75 ml) of thionyl chloride is slowly added dropwise. The reaction mixture was refluxed for 12 hours, then cooled, 1.5 liters of toluene and precipitated 1'-Chloro (4'-chloro ^, r-4-biphenyl) -2i (1,2'-chloro-4'-chloro ⁾ hydrochloride were added. After aspiration (4-thiazol-11-yl) ethane is taken up with 2 liters of water after suction. Addition of sodium bicarbonate gave the free base which was taken up in chloroform, dried over sodium sulfate and the solvent was distilled off. The residue crystallizes crystalline. There was obtained 148 g (92% of theory) of 1-chloro (4'-chloro-4-biphenylyl) -2- (1'-biphenyl-4-yetethan), m.p. 118 ° C.

Preparation of starting material;

OH

150 g (0.5 mol) of N- (l, _{2,4-triazql-L-yl)} -4- (4'-chlorophenyl) acetophenone was dissolved in 1,000 ml of methanol and rozfp / u at 0 'to 10 ° C was added portionwise with stirring 23 g (0.55 mol). sodium borohydride. Resulting. The mixture is stirred at room temperature for 1 hour and then heated to boiling for 1 hour After distilling off the solvent, the residue is briefly heated with 1000 ml of water and 300 ml of concentrated hydrochloric acid. After the reaction mixture is made alkaline with sodium hydroxide solution, the reaction product can be filtered off. 140 g (97% of theory) of 1- (4'-chloro-4-biphenylyl) -1-hydroxy-2- (1,2,4-triazol-1-yl) -ethane are obtained. C.

Preparation of starting material:

C1-C18H-co-CH, 31 g (0.1 mol) of ω-bgom-4t (4'-chlorophenyl) acetophenone was mixed with 13.8 g (0.1 mol) of discharged potassium carbonate, and 13 g (0.2 mol) of 1,2,4'-riazole in 200 ml of acetone are heated to boiling under stirring for 12 hours. 800 ml of water are added to the cooled suspension and the mixture is filtered off with suction. The solid reaction product is recrystallized from a mixture of isopropanol and dimethylformamide to give 17.1 g (57% of theory) of ω- (ШШШШгЫЫ) -4- (4'-chlorophenyl) acetophenone, m.p. 213 ° C.

By analogy to the procedure of Example 1, also general products are obtained; of formula I summarized in the following table 1.

Table · 1

R

-, example number Rn

Melting point (° C)

2,4-012

4-0 - (OV Cl

158 (decomposition) (x HNOs)

2,4-012

2,4-012

2,4-012

2,4-012

C (CI%)

GI ČI

Cl

Cl Cl

135 (decomposition) (XHNO3)

182 (x HNO3)

H. 147 - 150 (X HCl)

24 clone

Cl

OBJECT OF THE INVENTION

Claims (2)

A fungicidal and plant-growth regulating composition, characterized in that it contains at least one (1-phenyl-2-triazolylethyl) thioether of the formula I as defined in claim 1, characterized in that the derivatives are 1-halo-1-phenyl -2-triazolylethane of formula II, X UU in which in which R represents a halogen atom, an optionally chlorinated phenyl group or an optionally chlorinated phenoxy group n is a number of 0 to 3 and R 'represents a hydrogen atom, a methyl group, a phenyl group optionally substituted by chlorine and / or an alkyl of up to 4 carbon atoms, or represents an optionally chloro-substituted benzyl group, or a salt thereof. 2. A process for the preparation of active substances according to claim 1 Wounds have the meanings given above and X is halogen, reacted with mercaptans of formula III, R’ — S — Η (III) in which R 'is as defined above, optionally in the presence of a diluent and an acid binding agent, at a temperature between 20 and 150 degrees Celsius, preferably at the boiling point of the diluent used.