CS241499B2 - Plant growth regulation agent and fungicide and active component production method - Google Patents

Description

The present invention relates to plant growth regulating compositions and fungicidal compositions containing the novel 1-hydroxyethylazole derivatives as active ingredient. The invention further relates to a process for the preparation of these new active substances.

It is already known that certain 2-haloethyltrialkylammonium halides have the ability to regulate plant growth (Ser. U.S. Pat. No. 3,156,554). Thus, for example, 2-chloroethyltrimethylammonium chloride can influence the growth of plants, in particular the suppression of vegetative plant growth in important crop plants. However, the efficacy of this substance, especially at low rates of application, is not always sufficient.

It is further known that 2-chloroethylphosphonic acid has the ability to control plant growth (cf. DOS 1 667 968). However, the results obtained with this substance are not always satisfactory either.

It is further known that zinc ethylene-1,2-bisdithiocarbamate is a good means of combating fungal diseases of plants [cf. Phytopathology 33, 1113 (1963)]. Its. however, use is only possible to a limited extent, since it is not always satisfactory in particular at low application rates and concentrations.

We have now found novel 1-hydroxyethylimidazole derivatives of the general formula I

Ol · '

Y-C-R

í π in which

R is tert-butyl or optionally chloro-substituted phenyl,

Y denotes -OCH ₂ - or -CH ₂ -CH ₂ -,

Z is fluoro, chloro, methyl or optionally substituted phenyl and m is 1 or 2, as well as their addition salts with hydrochloric acid and naphthalene-1,5-disulfonic acid, which have the ability to control plant growth and further have a fungicidal effect .

The compounds of formula I have an asymmetric carbon atom and can therefore be formed in both optical isomeric forms. The present invention relates to both mixtures of isomers and individual isomers.

According to the invention, the 1-hydroxyethylimidazole derivatives of the formula I are produced by the oxiranes of the formula II, ΧθΗ-χ *

-m. O-CH £

In which:

R, Y, Z and m are as defined above, in reaction with an imidazole of formula III

(III) in the presence of a diluent and optionally in the presence of a base, whereupon hydrochloric or naphthalene-1,5-disulfonic acid is optionally added to the compounds of formula I obtained.

Accordingly, the present invention provides plant growth regulating agents and fungicidal compositions which comprise at least one 1-hydroxyethylimidazole derivative of the formula I or its addition salt with hydrochloric acid or naphthalene-1,5-disulfonic acid as active ingredient.

Surprisingly, the 1-hydroxyethylimidazole derivatives of the formula I according to the invention show a better plant growth regulating ability than the known 2-chloroethyltrimethylammonium chloride and also the known 2-chloroethylphosphonic acid, which are known to be well active substances with the same type of action. In addition, the compounds of the invention surprisingly have a better fungicidal action than the zinc ethylene-1,2-bisdithiocarbamate, which is the closest related compound in terms of activity. The active compounds according to the invention thus represent an enrichment of the technique.

The 1-hydroxyethylimidazole derivatives of the invention are generally defined in Formula I.

Particularly preferred are those compounds of formula I wherein

R is tert-butyl, or chloro substituted phenyl,

Z represents fluoro, chloro, methyl, and optionally substituted chloro atoms, and

Y and in have the meanings given in Formula I.

In addition to the compounds exemplified in the examples illustrating the process for the preparation of the active compounds, the following compounds of the general formula I can be mentioned individually

OH

Y-C-R i

(O

Table 1

3,4- (¾

C (CH3) ₃

-C _{(CH3) 3}

-C (CH ₃ ) ₃ —O — CH ₂ - —o — ch ₂ - —o — ch ₂ -

—OCH2— “© ^_CÍ —0 — ch ₂ - _3,4-Cl2 —0 — CH2— 70) - ¹ —0 — ch ₂ - - CH (CH _{3) 3} and- —0 — ch ₂ - -CH (CH _{3) 3 3,4-Cl2} —0 — ch ₂ - - CH _{(CH3) 2} * - <o> —Ch ₂ —ch ₂ - -C (CH ₃ ) ₃ whose -ch ₂ -ch ₂ - -C (CH _{3) 3,4-Cl2} —Ch ₂ —ch ₂ - -C (CH ₃ ) ₃

-ch ₂ —ch ₂ +2> * - <§> - Cl

-CH, -CH, -

_3,4-Cl2 —Ch ₂ —ch ₂ - —Ch ₂ —ch ₂ - -CH (CH _{3] 2} -^ O O ^ c -ch ₃ -ch ₂ - -CH (CH _{3) 2} 2,4-Cl ₂ -ch ₃ -ch ₂ - 3,4-Cl2 -CH (CH _{3) 2} _ch ₂ -ch ₂ - -C (CH ₃ ) _{3 4-CH3} -ch ₃ -ch ₂ - -C (CH ₃ ) ₃ 4-C1, _2-CH3 , -ch ₃ -ch ₂ - -C (CH ₃ ) ₃ 4-F —0 — ch ₂ - -C (CH ₃ ) ₃

If, for example, 2- (4-chlorophenoxymethyl) -2-tert-butyl-oxirane and imidazole are used as starting materials, the reaction scheme can be illustrated as follows:

Cl

TQ ^ OC ^ -C-CICH + A 0-CH ₂ -> Cl- ^ Oy-O-CH ₂ -C -CH 2 CH ₉ ά

The oxiranes used in the process of the invention as starting materials are generally defined by Formula II. In this formula, the symbols R, Y, Z and the index m preferably have those meanings which have already been mentioned as preferred for the description of the compounds of the formula I.

The oxiranes of formula II are novel compounds. Their preparation is described in MS. No. 241 500.

The imidazole of formula III, which is further used as the starting material, is a generally known compound of organic chemistry.

Suitable diluents for the reaction according to the invention are preferably all inert organic solvents. These preferably include alcohols such as ethanol and xethoxyethanol, ketones such as 2-butane, nitriles such as acetonitrile, esters such as ethyl acetate, ethers such as dioxane, aromatic hydrocarbons such as benzene and toluene, or amides such as dimethylformamide.

Suitable bases for the reaction according to the invention are all customary inorganic and organic bases. These preferably include alkali metal carbonates such as sodium carbonate and potassium carbonate, alkali metal hydroxides such as sodium hydroxide, alkali metal alkoxides such as sodium and potassium methoxide and ethoxide, alkali metal hydrides such as sodium hydride, as well as lower tertiary alkylamines, cycloalkylamines and aralkylamines such as, in particular, triethylamine.

The reaction temperatures can be varied within a wide range when carrying out the process according to the invention. In general, the reaction is carried out at temperatures between 0 and 200 ° C, preferably between 60 and 150 ° C.

The reaction according to the invention can optionally be carried out at elevated pressure. In general, the pressures are carried out at pressures of 0.1 to 5.0 MPa, preferably between 0.1 and 2.5 MPa.

In the process according to the invention, preferably 1 to 2 mol of imidazole and optionally 1 to 2 mol of base are used per mole of oxirane of the formula II.

The isolation of the reaction products is carried out in a generally conventional manner.

The compounds of the formula I obtained by the process according to the invention can be converted into addition salts with hydrochloric or naphthalene-1,5-disulfonic acid.

Hydrochloric acid and naphthalene-1,5-disulfonic acid are suitable for the preparation of physiologically acceptable acid addition salts of the compounds of the formula I.

Acid addition salts of the compounds of formula (I) may be obtained in a simple manner according to conventional salt-preparation methods, for example by dissolving the compound of formula (I) in a suitable inert solvent and adding hydrochloric acid or naphthalene-1,5-disulfonic acid. optionally purified by washing with an inert organic solvent.

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 the type of action of the plant growth regulators, it has been hitherto known that the active substance can exert one or several different effects on the plants. 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 regulators can be used, for example, to suppress vegetative plant growth. Such inhibition of growth is of economic importance, inter alia, in grassland, since by suppressing grass growth, for example, the frequency of mowing in ornamental gardens, parks and sports facilities, at the edges of roads, airports and orchards can be reduced.

It is also important to suppress the growth of herbaceous and woody plants at roadside and close to overhead lines or, in general, where strong growth is undesirable.

It is also important to use plant growth regulators to suppress crop growth in grain as this will reduce or eliminate the risk of plants lying down before harvest due to crop shortening. In addition, plant growth regulators can cause grain stalks to increase, which also counteracts lodging. The use of growth regulators to shorten the stalks and strengthen the stalks allows the application of higher amounts of fertilizer to increase yields, without worrying about crop lodging.

The suppression of vegetative growth permits denser sowing or planting of many crops, so that yields per unit area can be increased. The smaller plants thus grown also have the advantage that the culture is easier to cultivate and harvest.

Suppression of vegetative growth of plants can also lead to increased yields, as nutrients and assimilates are used more intensively for the formation of flowers and fruits than for the growth of vegetative parts of plants.

Stimulation of vegetative growth can often be achieved by growth regulators. This is of great importance when vegetative parts of plants are harvested. However, the stimulation of vegetative growth can at the same time also lead to stimulation of generative growth by producing more assimilates, so that for example more fruits can be formed or larger fruits can be produced.

Increased yields can also be achieved in many cases by interfering with plant metabolisms without observing changes in vegetative growth. Growth regulators can also act on changes in the composition of plants, which in turn can achieve a better quality of harvested products. Thus, for example, it is possible to increase the sugar content of sugar beet, cane, pineapple as well as citrus fruits, or to increase the protein content of soy or grain. Furthermore, the degradation of desired substances contained in plants, such as sugar in sugar beet or sugar cane, can be inhibited by, for example, growth regulators before or after harvesting.

In addition, the production or efflux of secondary plant substances can be positively influenced. An example is the stimulation of latex effluent in rubber trees.

Parthenocarpic (seedless) fruits can also be produced by growth regulators. Furthermore, it is possible to influence the sex of the flowers with these regulators. Pollen sterility can also be achieved, which is of great importance in breeding and hybrid seed production.

By using growth regulators it is possible to control the formation of side shoots in plants. On the one hand, the development of side shoots can be promoted by violating apical dominance, which may be particularly desirable, especially in the cultivation of ornamental plants, in conjunction with growth suppression. On the other hand, it is also possible to inhibit the growth of the side shoots. This effect is of particular interest, for example, in tobacco growing or tomato planting.

The effect of the active ingredients on the plant print can be controlled so that the plants can be completely de-leafed at the desired point in time. Such defoliation is important for facilitating the mechanical harvesting of cotton, but it also plays a major role in other crops, such as the vine, where it facilitates harvesting. Plant defoliation can also be performed to reduce plant transpiration before transplanting.

Growth regulators can also control the fall of fruit. On the one hand, premature fruit loss can be prevented. On the other hand, it is also possible to support the fall of fruits or even flowers in the sense of a kind of “chemical thinning” to break the so-called “alternatives”. An alternative is the special behavior of some fruits, based on endogenous, very different yields from year to year. Growth regulators can also be used to reduce the force required at harvest time to tear off fruits in crop plants, so that mechanical harvesting or manual harvesting is facilitated.

Further, growth regulators can be used to accelerate or slow down the ripening of harvested products before or after harvesting. This is particularly advantageous since it can be optimally adapted to market requirements. Furthermore, growth regulators can in many cases serve to improve the coloring of the fruit. In addition, growth regulators can achieve a concentration of fruit ripening within a certain period of time. This creates the prerequisites for, for example, tobacco, tomatoes or coffee to be fully mechanically or manually harvested in only one working stage.

The use of · growth regulators can also influence seed stand or bud period, ie endogenous annual rhythm, so that plants such as pineapple or ornamental plants in horticulture germinate, sprout or bloom when they would not germinate under normal conditions, . nekvetly.

Growth regulators can also achieve delayed bud sprouting or delayed seed germination, for example to prevent late frost damage in colder climate areas.

Finally, resistance to frost, drought or high salt content in the soil can be induced by the growth regulators, which allows the plants to be grown in areas that would normally be unsuitable for the plants.

The active compounds according to the invention also show a strong microbicidal action and can be used in practice to combat undesirable microorganisms. The active compounds described are suitable for use as plant protection agents.

Fungicidal compositions are used in plant protection to control fungi of the classes Plasmodiopboromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.

Since the plants of the present invention are well tolerated at the concentrations required to combat fungal diseases, the compounds can be used for the treatment of aboveground parts of plants, seedlings and seeds, as well as for the treatment of soil.

As plant protection agents, the active compounds according to the invention with particularly good results can be used for combating fungi which cause disease with true powdery mildew, such as for combating Erysiphe species, for example to combat powdery mildew or Erysiphe graminis.

It is particularly advantageous that the active compounds according to the invention not only have a protective effect, but are also systemically active, which makes it possible to protect the plant against fungal infestation by feeding the active substance to the aerial parts of the plant via soil and root system or via seeds.

The active compounds can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granulates, aerosols, small particles coated with polymeric substances and seed coatings, as well as ULV formulations.

These compositions are prepared in known manner, 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. reagents.

If water is used as a filler, it is also possible to use, for example, organic solvents as co-solvents. Basically suitable liquid solvents are: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as. cyclohexane or paraffins, 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 cycloliexanone, strongly 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 pressure, for example aerosol propellants such as halogenated hydrocarbons, as well as butane, propane, nitrogen and carbon dioxide. Suitable solid carriers are natural stone meal, such as kaolins, alumina, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and synthetic stone meal, such as highly disperse silica, alumina and silicates. Suitable solid carriers for the preparation of granulates are crushed and fractionated natural stone materials such as limestone, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, shells coconut, corn sticks and tobacco stems. Suitable emulsifiers and / or foaming agents are non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, fatty alcohol polyoxyethylene ethers, e.g.

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

In addition, these compositions may contain coloring agents such as inorganic pigments, for example iron oxide, titanium dioxide and ferrocyanide blue, and organic coloring agents such as alizarin dyes and metallic azo-phthalocyanine dyes, as well as trace elements such as iron, manganese, boron, copper, cobalt, molybdenum and zinc.

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

The active compounds according to the invention can be present in the formulations in admixture with other known active compounds such as fungicides, insecticides, acaricides, herbicides, as well as in mixtures with fertilizers and other plant growth regulators.

The active compounds can be applied as such, in the form of concentrates, or of their ready-to-use forms, as ready-to-use solutions, emulsifiable concentrates, emulsions, foams, suspensions, wettable powders, pastes, soluble powders, dusts and granules. Application can be carried out in the usual manner, for example by watering, spraying, spraying, sprinkling, dusting, dusting, foaming, painting, etc. Further, it is possible to apply the active substances by the so-called ULV method or to apply the active agent or even the active substance itself. Plant seed may also be treated.

When the compounds of the invention are used as plant growth regulators, the amounts applied can vary within wide limits. In general, 0.01 to 50 kg, preferably 0.05 to 10 kg, of active substance are used per 1 ha of surface.

When using the substances according to the invention as plant growth regulators, the application is carried out within a convenient time interval, the exact definition of which is governed by climatic and vegetative conditions.

When the compounds according to the invention are used as fungicides, the application rate can vary within wide limits depending on the type of application. Thus, the concentration of active ingredients in the treatment of plant parts varies in general from 1 to 0.0001% by weight, preferably between 0.5 and 0.001% by weight. In the treatment of seed, an amount of active compound of from 0.001 to 50 g per kg of seed, preferably from 0.01 to 10 g per kg of seed, is generally required. In the treatment of the soil, active compound concentrations of from 0.00001 to 0.1% by weight, preferably from 0.0001 to 0.02%, are required at the point of action.

Examples illustrating the method of production of active ingredients:

Example 1 (1-2)

OH

241

Κ 2.71 g (0.1178 mol) sodium in 250 ml absolute ethanol was added 8.02 g (0.1178 mol) imidazole. A solution of 14.17 g (0.0589 mol) of 2- (4-chlorophenoxymethyl) -2-tert-butyloxirane in 100 ml of ethanol is added dropwise at room temperature over 30 minutes. The reaction mixture was then heated at reflux for 8 hours, concentrated and taken up in ether. The ether extract was neutralized three times with 1N hydrochloric acid solution and the combined phases in hydrochloric acid were neutralized with sodium bicarbonate and then washed with ethyl acetate. Concentration and recrystallization from cyclohexane gave 11.6 g (64%) of 2- (4-chlorophenoxymethyl) -3,3-dimethyl-1- (imidazol-1-yl) butan-2-ol, m.p. 154 to 155 ° C.

Production of starting material:

(Π — 1)

C y 2 O-CH 2 C (CH ₃ ) ₃ O-CH ₂

To a solution of 189 mL (2.0 mol) of dimethyl sulfate in 1200 mL of absolute acetonitrile at room temperature was added a solution of 162 mL (2.2 mol) of dimethylsulfide in 400 mL of absolute acetonitrile, and the reaction was allowed to stir overnight at room temperature. 118.8 g (2.2 mol) of sodium methoxide are added and the reaction mixture is allowed to stir for 30 minutes and then a solution of 272 g (1.2 mol) of 1- (4-chlorophenoxy) -3 is added dropwise over 30 minutes. 3-dimethylbutan-2-one in 600 ml of absolute acetonitrile, the reaction mixture is left stirring overnight, then the reaction mixture is concentrated, the residue is partitioned between water and ethyl acetate, the organic phase is separated, washed twice with water and once with saturated sodium chloride solution, It is dried over sodium sulphate, concentrated and the residue is distilled under vacuum to give 242.4 g (84% of theory) of 2- (4-chlorophenoxymethyl) -2-tert-butyloxirane, b.p. 115 DEG-122 DEG C./0. M.p. 50-52 ° C.

The following compounds of formula I are obtained in an analogous manner:

Table 2

OH

il) example Z _m Y number

R melting point (° C)

12 2,4-Cl ₂ 4-CH, -O-CH ₂ - -C (CH ₃ ) ₃ 152—154 13 —O — ch ₂ - C (CH ₃ ) ₃ 129—131 14 _2-CH3 _o — ch ₂ - -C (CH ₃ ) ₃ 123—124 15 Dec 4-Cl, 2-CH3 —O — ch ₂ - -C (CH ₃ ) ₃ 157—159 16 4-C1 -ch ₂ -ch ₂ - -C (CH ₃ ) ₃ 157.5—159.5 17 4-F -ch ₂ -ch ₂ - -C (CH ₃ ) ₃ 124—125 18 2-CH., _ch ₂ -ch ₂ - -C (CH ₃ ) ₃ 94— 99 22nd 4-C1 —0 — ch ₂ - whose 216—217 (x 1/2 NDS) ’ 27 Mar: 2,4-Cl ₂ _ch ₂ -ch ₂ - -C (CH ₃ ) ₃ 118—119 28 —O — ch ₂ - -C (CH ₃ ) ₃ 169—170.5 29 2-C1 —O — ch ₂ - -C (CH3) ₃ 122—124

example Z _m Y R melting point number (° C) Whose 33 4 - C1 -O-CH ₂ - ToV 135.5 - 134 37 4-F - O-CH ₂ - \ - ~ from -C (CH3) ₃ 141—142 39 3-C1 -O-CH ₂ - -C (CH ₃ ) ₃ 124 40 2-C1, 4-F - O-CH ₂ - -C (CH ₃ ) ₃ 137 44 4-CH, -CH ₂ —CH ₂ - -C (CH ₃ ) ₃ 101—103 46 d -O-CH ₂ - -C (CH ₃ ) ₃ 174—176 * NDS = 1,5-Naphthalenedisulfonic acid Good the activity of the compounds according to the invention is Example A illustrated by the following examples. In these examples, Stimulation of carbon dioxide assimilation in sol- The following compounds have been used: gods O solvents: II 30 parts by weight of dimethylformamide (Aj = Cl- _{-CH2 -CH2} -P-OH emulsifier: | 1 part by weight polyoxyethylenesorbi- OH tanmonolaurate 2-chloroethylphosphonic acid To get a suitable one active agent

^(B) C ⁼ CH ₂ CH ₂ N (CH _{3) 3} Cl

2-chloroethyltrimethylammonium chloride p

(C) =

CW, -A / H-C-S

I Zp.

NH-CH _Z ^X EN ethylene-l, 2-bisdithiocarbamate zinc EXAMPLES biological activity.

Table A is mixed with 1 part by weight of the active ingredient with the indicated amounts of solvent and emulsifier, and the mixture is diluted with water to the desired concentration.

Soybean plants are grown in the greenhouse until the first assimilation leaf is fully developed. At this stage, the plants are sprayed with the active ingredients up to the wetting stage. In the next phase of the experiment, assimilation of carbon dioxide by the plants is measured and expressed as a percentage of carbon dioxide fixation compared to control plants not treated with the active compounds. Value 100 why. indicates fixation of carbon dioxide corresponding to fixation in the case of control plants.

Table A lists the test compounds, the concentrations of compounds used and the results of the described ¹ test.

Stimulation of carbon dioxide assimilation in soybeans active compound concentration in% CO ₂ fixation in% control

100 ALIGN!

Whose

Cl ₂ -CH ₂ CH ₂ C-CH ₃ CHn

0.05 (known from U.S. Pat. No. 4,123,542) active compound concentration in% CO ₂ fixation

0.05 (known from U.S. Pat. No. 4,123,542)

OH

O-CH 2 CC (CH ₃ ) ₃

0.05

109

CH,

1-2 (1-27)

Example B

Test for Erysiphe graminis (barley) / protective effect solvent:

100 parts by weight of dimethylformamide emulsifier:

0.25 parts by weight of alkylaryl polyglycol ether

To prepare a suitable active ingredient, 1 part by weight of active ingredient is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

To determine protective activity, young plants are sprayed until wetted with the active agent. After the spray coating has dried, the plants are dusted with spores of Erysiphe graminis f. Sp. hordei.

The plants are then stored in a greenhouse at a temperature of about 20 ° C and a relative air humidity of about 80 to create favorable conditions for the development of typical powdery mildew spots.

days after inoculation, evaluation of the experiment is performed.

The following table B shows the active substances tested, the active substance concentrations and the results obtained.

Table B

Test for Erysiphe graminis f. Sp.

active ingredient hordei (barley) / protective effect of active ingredient concentration in spray suspension in ° / o weight attack in ° / o untreated control plants

CH 2 NH-CS \

Zrx

0,025

100 ALIGN!

CHfNH-CS (known) (C) active substance concentration of the active substance in the spray suspension in% by weight of disease attack in% of untreated control plants

0,025

0,025

0,025

0.0

0.0

0.0

(15)

0,025

Example C

Test for apple scab (Venturia inaequalis) (apple tree / solvent protective effect):

4.7 parts by weight · acetone emulsifier:

0.3 part by weight of alkylaryl polyglycol ether

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

In order to determine protective activity, young plants are sprayed with the active preparation up to the wetting stage. After the spray coating has dried, the plants are inoculated with an aqueous suspension of apple scab (Venturia inaequalisj) and kept in an incubation chamber at 20 ° C and 100% relative humidity for 1 day.

The plants are then placed in a greenhouse at 20 ° C and a relative air humidity of about 70%.

days after inoculation, evaluation of the experiment is performed.

The following table C lists the active substances to be tested, the active compound concentrations and the test results.

Table C

Test for apple scab (Venturia inaequalisj (apple / protective effect of active substance attack in% at (active substance concentration 100 ppm)

^Ch ~ 3 ^ OC ^ -C, _C H _{3) 3} 'of

OH _F __ V _{z z 2 2} cc (ch ₃ j ₃

CH _%

Claims (2)

Subject Plant growth regulating agent and fungicidal agent, characterized in that it contains at least one 1-hydroxyethylimidazole derivative of the general formula I (I) as an active ingredient. A compound of the formula I as claimed in claim 1, characterized in that the oxlrans of the formula II (O) - R, Y, Z and m have the meanings given in 1; R is tert-butyl or optionally chloro-substituted phenyl, Y represents - OCH ₂ - or _CH ₂ -CH ₂ -, Z is fluoro, chloro, methyl or optionally chloro-substituted phenyl; and m is 1 or 2, or an acid addition salt thereof with hydrochloric acid or naphthalene-1,5-idisulfanoic acid. 2. A process for the preparation of the active ingredient according to (III) in the presence of a diluent and optionally in the presence of a base, whereupon hydrochloric acid or naphthalene-1,5-disulfonic acid is optionally added to the compounds of the formula I obtained.