FI71732C - 1-hydroxyethyl azole derivatives, their preparation process and their use as growth regulators for plants and as fungicides. - Google Patents

Description

1 71732 1-Hydroxyethylazole derivatives, their preparation method and use as a plant growth regulator and fungicide 5 Separated from application 811472

The present invention relates to novel 1-hydroxyethylazole derivatives, to a process for their preparation and to their use as plant growth regulators and fungicides. It is known that certain 2-haloethyltrialkylammonium halides have plant growth regulating properties (cf. U.S. Pat. No. 3,156,554). Thus, for example, 2-chloroethyltrimethylammonium chloride can be used to influence plant growth, in particular to inhibit the vegetative growth of important crops. However, the efficacy of these substances, especially when used in relatively small amounts, is not always sufficient.

It is also known that 2-chloroethylphosphonic acid has an inhibitory effect on plant growth (cf. DE-OS 1667968). However, experiences with these substances are not always satisfactory either.

In addition, zinc ethylene-1,2-bistiocarbamidate is known to be a good compound in the fight against fungal diseases of plants (cf. Phytop thology 33 (1963) 1113). However, its use is only limited, as it is not always effective enough, especially at relatively small amounts and concentrations.

New women of the 1-hydroxyethylazole derivative of formula (I) 2 oh 717 3 2 have been discovered.

(O '> -Cl [= Cll-C-R

ζΛ- /

lfN'N

5 N__ii (I) 10 wherein R is t-butyl, Z is chlorine, fluorine or methyl and m is 1 or 2, 15 and their acid salts and metal salt complexes.

The compounds of formula (I) have one asymmetric carbon atom and may exist as both optical isomers and in addition as two geometric isomers. The present invention relates to both mixtures of isomer-20 and individual isomers.

It has further been found that 1-hydroxyethylatoluene derivatives of formula (I) are obtained by administering 25? -V / o y-ciircyl-c-R of the oxiranes of formula (II).

0- CU

* 'm wherein R, Z and m are as defined above, react with azoles 30 of formula (III)

II

In the presence of a diluent and optionally a base, an acid or a metal salt is optionally added to the compound of formula (I) obtained.

In addition, it has been found that the novel 1-hydroxyethyl azole derivatives of formula (I) have potent plant growth regulating and fungicidal properties.

Surprisingly, the 1-hydroxyazole derivatives of the invention and the formula (1) have a stronger plant growth-regulating effect than the known 2-chloroethyltrimethylammonium chlorides and, as well as the known 2-chloroethylphosphonic acids, which are known to be effective in similar activity. In addition, the substances according to the invention surprisingly have a better fungicidal effect than the known zinc ethylene-1,2-bisdithiocarbamidate, which is a compound with a similar mode of action. The substances according to the invention thus have an important practical significance.

The oxiranes used as starting materials in the preparation process of the invention are generally defined by formula (II). In the formula, R, Z and m are as defined in the definition of the substances of formula (I) according to the invention. Oxiranes of formula (II) ^ -0-CH = CH-C-R (II) m o-ch2 wherein R is t-butyl, Z is chlorine, fluorine or methyl and m is 1 or 2 are novel.

“71732

Oxiranes of formula (II) are obtained by reacting ketones of formula (IV) wherein R, Z and m are as defined above by reacting either - (1) dimethyloxosulfonium methylide with has the formula (V) 15 + Λ- (CH) 50 CH 2 CV) in the presence of a diluent, or /?) trimethylsulfonium methyl sulfate of the formula (VI) (-) (+) - (CH 3} 3 S J CH 3 SO 4 (VI) ) 25 in the presence of an inert organic solvent and a base.

The ketone of formula (IV) required as starting materials for the preparation of oxiranes of formula (II)! 30 are known (cf. DE-PS 2201063, DE-OS 2705678, DE-OS 2737H89, Tetrahedron 31 (1975) 3, Chemical Abstracts 84.73906η), or can be prepared in principle by known methods.

The dimethyloxo-35 sulfonium methylide of formula (V) required in Preparation (<*) is also known 717 3 2 (cf. J. Amer. Chem. Soc. 87 (1965) 1363-1364). It is used in the above reaction freshly prepared; reacting trimethyloxosulfonium iodide with sodium hydride or sodium amide in the presence of a diluent.

The trimethylsulfonium methyl sulfate of formula (VI) required in Preparation (./*) is also known (cf. Heterocycles 8 (1977) 397).

It is also used in the above reaction just prepared by the reaction between dimethyl sulfide and dimethyl sulfate.

In the preparation of oxiranes of the formula (II) a) e.g. dimethyl sulfoxide can be used as diluent.

15 The reaction temperatures in the above-mentioned preparation option (oO can vary over a fairly wide range. Generally, temperatures of 20-80 ° C are used.

The preparation of the oxiranes of formula (II) by method (X), as well as the isolation of the synthesis product from the obtained reaction mixtures, are carried out by conventional methods (cf. J. Amer. Chem. Soc. 87 (1965) 1363-1364).

In the preparation of oxiranes of formula (II) by the method Φ), e.g. acetonitrile can be used as the inert organic solvent.

In the preparation alternative), strong inorganic and organic bases can be used as the base. For example, sodium methylate can be used.

In the above-mentioned ready-30 option (/ 5), the reaction temperatures can vary within certain limits. In general, temperatures of 0 to 60 ° C, preferably room temperature, are used.

The preparation of the oxiranes of formula (II) by the method (/ *), as well as the isolation of the synthetic products, is carried out by conventional methods (cf. Heterocycles 8 (1977) 397).

6 71732

The oxiranes of formula (II) may optionally be used directly in the process of the invention, without isolation.

The azoles used as additional starting materials in the preparation process of the invention are generally defined by formula (III).

The azoles of formula (III) are compounds well known in organic chemistry.

Suitable diluents for the reactions according to the invention are all inert organic solvents. These are preferably alcohols such as ethanol and methoxyethanol; ketones such as 2-butanone; nitriles such as acetonitrile; esters such as acetic acid esters; ethers such as dioxane; aromatic hydrocarbons such as benzene and toluene, or amides such as dimethylformamide.

Suitable bases for the reactions according to the invention are all generally inorganic and organic bases. These preferably include alkali carbonates such as sodium and potassium carbonate; alkali hydroxides such as sodium hydroxide; alkali metal alcoholates such as sodium and potassium methylate and ethylate; alkali hydrides such as sodium hydride; as well as lower tertiary alkylamines, cycloalkylamines and arylalkylamines such as triethylamine.

The reaction temperatures when using the process according to the invention can vary within quite wide limits. In general, temperatures of 0 to 200 ° C, preferably 60 to 150 ° C, are used.

The reaction according to the invention can optionally be carried out under elevated pressure. Generally pressures of 1-50 bar, preferably 1-25 bar are used.

Using the preparation process 7 71732 according to the invention, 1 mol of oxirane of the formula (I) is mixed, preferably 1-2 mol of azole and optionally 1-2 mol of base. The final product is isolated as usual.

The compounds of formula (I) obtained by the process of the invention can be converted into acid salts or metal salt complexes.

For the preparation of physiologically acceptable acid salts from the compounds of the formula (I), the following acids can be used advantageously: hydrohalic acids, such as, for example, hydrochloric acid and hydrobromic acid, preferably hydrochloric acid, in addition to phosphoric acid, nitric acid, sulfuric acid, monocarboxylic acid, -icinic acid, succinic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, malic acid, lactic acid, and sulfonic acids such as p-toluenesulfonic acid and 1,5-naphthalenedisulfonic acid.

The acid salts of the compounds of formula (I) may be prepared simply by conventional salt formation methods, e.g. by dissolving a compound of formula Cl) in a suitable inert solvent and adding an acid, e.g. hydrochloric acid, and isolating conventionally, e.g. by filtration and optionally purifying by inert washing. with an organic solvent.

For the preparation of metal salts of the compounds of formula (I), salts of the main groups II-IV of the Periodic Table and of the metals of side groups I, II and IV-VIII, such as copper, zinc, manganese, magnesium, tin, iron and nickel, are preferably suitable. .

As the anions of the salts, anions obtained from the following acids are preferable: hydrohalic acids, such as hydrochloric acid and hydrobromic acid, in addition to phosphoric acid, nitric acid and sulfuric acid.

71732

Metal complexes of the compounds of formula (I) may be prepared simply by conventional methods, i.e. e.g. by dissolving the metal salt in an alcohol, e.g. ethanol and adding the solution to the compound of formula (I). The metal complexes can be isolated in the usual ways, e.g. by filtration and possibly purified by recrystallization.

The useful substances according to the invention penetrate the metabolic system of plants and can therefore be used as growth regulators.

It is known from experience to date that the mode of action of plant growth regulators is that the active substance can also have various other effects on plants. The effects of the substances obviously depend on the time when the use is started in the growing environment of the plant, as well as on the amounts of substances applied to the plants or their environment and on the method of administration of the substances. In any case, growth regulators must affect crops in a certain desired way. 20 Plant growth regulators can have an effect on, for example, inhibiting the vegetative growth of plants. Such a slowdown in growth is economically significant, especially for grasses, as it can reduce the frequency of mowing in ornamental-25 parks, park and sports fields, roadsides, airports or orchards. It is also important to slow down the growth of grass and tree plants along roadsides and in the vicinity of pipelines and pipelines, or generally wherever strong plant growth is detrimental.

It is also important to use growth regulators to curb the growth of cereal lengths. In this way, the risk of accumulation before harvesting is reduced or completely eliminated. In addition, growth regulators applied to cereals can cause stalks to strengthen, which also reduces varnish. When 71732 growth regulators are used to shorten and strengthen the stalks, larger amounts of fertilizer can be used to improve yield without the risk of grain breakage.

5 Curbing vegetative growth allows more crops to be planted more frequently, so quantitative yields can be made to grow. Another advantage of the smaller plants obtained in this way is that the cultivation and harvesting of the crops is easier.

10 Regulating vegetative growth can also improve yields in such a way that nutrients and contact products become more efficiently used to form flowers and fruits than quite growth.

Growth regulators can often also promote 15 vegetative growth. It is of great benefit when the vegetative parts of the plant are utilized. However, promoting vegetative growth can simultaneously lead to an improvement in generative growth, because the more contact products are formed, the larger or more fruits are produced.

Yields can in some cases be improved by affecting plant metabolism without significant changes in vegetative growth. In addition, growth regulators can achieve changes in plant composition that improve crop quality. Thus, for example, it is possible to increase the sugar content of sugar cane, sugar beet, pineapple and citrus fruits or to improve the protein content of soybeans or cereals. It is also possible, for example, to reduce the desired substances, such as, for example, sugar in sugar cane or beet. Decomposition before or after harvest using growth regulators. In addition, the yield and flow of secondary growth products can be improved. An example is the acceleration of the flow of latex of size 35 from rubber trees.

71732 10 When using growth regulators, infertile fruit may form. In addition, the sex of the flowers can be influenced. Pollen sterility can also be achieved, which is of great importance in the cultivation and processing of hybridization products.

By using growth regulators, plant branching can be controlled. On the other hand, by inhibiting the apical potency, it can promote the formation of side branches, which may be very desirable, especially in the case of growing ornamental plants, in connection with growth control. On the other hand, it is also possible to inhibit the growth of side branches. There is great interest in this effect, for example in the cultivation of tobacco and tomatoes.

The use of growth regulators can affect the stability of the leaves of plants 15 in that way. That the plants drop their leaves at the desired time. This is important not only in the mechanical harvesting of cotton, but also in viticulture to facilitate harvesting. Removal of plant leaves may also precede replanting of plants to minimize plant respiration.

Similarly, growth regulators can control the fall of the fruit. On the other hand, premature fruit removal can be prevented.

On the other hand, the fall of fruit or even the fall of flowers can also be caused to the desired extent, in order to reduce the alternative. AlternanssiJla is understood as the property of some fruit species to produce very different hundreds each year. In addition, it is possible to make the fruit easier to peel off at harvest time, to allow mechanical picking or to facilitate manual picking.

In addition, growth regulators can accelerate or slow the maturation of harvested products before or after 35 harvests. This is particularly advantageous when the market needs can be monitored as closely as possible. In addition, growth regulators can in some cases improve fruit color. In addition to the above, growth regulators can provide a temporal concentration of maturation. Thus, preconditions are created for the fact that, for example, the harvesting of tobacco, tomatoes or coffee can be carried out at once, either completely mechanically or by hand.

In addition, the use of growth regulators can provide germination and sprouting peace for plants, such that plants, e.g., anas or ornamental plants in gardens, germinate, water, or bloom all at the same time, for which they do not normally show any readiness.

It may be desirable to slow seedling growth or seed germination by growth regulators in frost-prone communities to avoid damage caused by late frosts.

In addition, growth regulators can improve plant resistance to frost, drought, or high soil salinity. This makes it possible to cultivate plants in areas which have hitherto been normally unusable.

The substances according to the invention also have a strong antimicrobial effect and can be used for the control of harmful microorganisms. The substances are suitable for use as plant protection products.

Fungicides are used in plant protection against Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.

The good suitability of the substances for plants to control plant diseases in the amounts necessary makes it possible to treat above-ground parts of plants, seedlings and seeds, and soil.

In plant protection, the preferred substances according to the invention can be used with very good success against 71732 12 fungi which cause actual hay fever diseases; thus against Erysiphe species such as barley and cereal mildew (Erysiphe graminis).

It is particularly noteworthy that the substances according to the invention are not only prophylactic but also have a systemic effect. Thus, it is possible to protect plants from fungal infections when the substance is applied to the soil, roots, seeds or above-ground parts of the plants.

The substances can be used in conventional forms, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, sprays, encapsulated in polymers and seed coatings in ULV (ultra low volume) form.

These products are prepared in a conventional manner, e.g. by mixing the active ingredients in a medium, i.e. with liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surfactants, i. emulsifying and / or dispersing and / or foaming agents. When water is used as the medium, e.g. organic solvents can also be used as co-solvents. Suitable liquid solvents are preferably: aromatic hydrocarbons, such as toluene, xylene or alkylnaphthalenes; chlorinated aromatic hydrocarbons or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride; aliphatic hydrocarbons such as cyclohexanes or paraffins, e.g. petroleum fractions; alcohols such as butanol or glycol, and its ethers and esters; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone; strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, 35 and water. By buoyant gaseous intermediates or carriers are meant liquids that are gaseous at normal pressure and temperature, e.g., spray propellants such as halogenated hydrocarbons, as well as butane, propane, nitrogen, and carbon dioxide. Examples of solid carriers which can be used are naturally occurring fine rock types, such as kaolin, earth, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and synthetic fine powders, such as fine silicic acid, alumina and silica. Carriers for the granules include: e.g., crushed and crumbled natural stones such as calcite, marble, pumice, sepiolite, dolomite, and synthetic granules made from inorganic and organic powders, and organic materials such as sawdust, coconut shell, coconut shell granules obtained. As emulsifiers and foaming agents, nonionic or anionic emulsifiers can be used, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Lysine sulphite lye and methylcellulose, for example, can be used as dispersants.

Adhesives such as carboxymethylcellulose, natural and synthetic powdered, granular or latex-like polymers such as gum arabic, polyvinyl alcohol or polyvinyl acetate may be used in the products.

Dyes such as inorganic pigments, e.g. iron oxide, titanium oxide or ferrocyanine blue, and organic dyes, such as alizarin, azo or metal phthalocyanine dyes, as well as trace elements, such as iron, manganese, boron, copper, cobol 35, can be used. , salts of molybdenum and zinc.

The products generally contain 0.1 to 95% by weight, preferably 17 to 17% by weight, of active ingredient.

The substances according to the invention may be present in the products in admixture with other known active substances, such as fungicides, insecticides, acaricides and weeds, fertilizers and other growth regulators.

The active compounds can be used as such, in the form of the abovementioned products or in preparations prepared therefrom, such as ready-to-use solutions, emulsifiable concentrates, emulsions, foams, suspensions, spray powders, pastes, soluble powders, dusts and granules. They are used in the usual way, e.g. by wetting, spraying, sprinkling, spraying, foaming, brushing, etc. In addition, it is possible to use the active substances as ULV products or the preparation or the substance itself can be sprayed directly into the soil. Plant seeds can also be treated.

When the compounds according to the invention are used as plant growth regulators, the application rates can vary within wide limits. In general, 0.01 to 50 kg, preferably 0.05 to 10 kg, of active ingredient are used per hectare.

The plant growth regulators of the invention are used at a suitable time, which is determined in more detail by climatic and other growth conditions.

When the substances according to the invention are used as fungicides, the application rates can vary within wide limits depending on the mode of administration. Thus, the concentrations of active substance in the treatment of plant parts are from 1 to 0,000% by weight, preferably from 0.5 to 0.001% by weight. When treating seeds, the amounts required are from 0.001 to 50 g per person. When treating the soil, concentrations of 0.0000 to 0.1% by weight, preferably 0.0001 to 0.02% by weight, in the area of action are necessary.

5 15 • ^ ··· 71732

a production example

Example 1 / τΛ

Cl— ((J VCH = CH-C-C (CH3) 3 (1-1)

'-' CH

»1 (trans)

fi N

10 N _’J

To a solution of 5.8 g (0.2 mol) of sodium hydride in 200 ml of absolute dimethylformamide is added, with stirring at room temperature, 13.8 g (0.2 mol) of 1,2,4-triazole. After completion of the reaction, a solution of 23.7 g (0.1 mol) of 2- (4-chloro-phenylethenyl) -2-tert-butyloxirane in 50 ml of absolute dimethylformamide is added dropwise to the mixture. The reaction mixture is heated at 80 ° C for 4 to 20 hours and then poured onto crushed ice. The precipitated solid is filtered off with suction and mixed with the vinegar ester. The resulting organic solution is washed with water, dried and evaporated under reduced pressure. The evaporation residue is chromatographed on silica gel using a 1: 1 mixture of methylene chloride and ethyl acetate. After evaporation of the eluate, the residue is recrystallized from naphtha. 1- (4-chlorophenyl) -4,4-dimethyl-3- (1,2,4-triazol-1-ylmethyl) pent-1-en-3-ol (trans form) is obtained in the form of a solid, having a melting point of 115-117 ° C.

In a similar manner, the following compounds of formula (I) are obtained:

Table 1 717 3? (Q V- CH = CH-C-R (I) -J CH- Z, 2 m N.

f "f 1 ° 1

OF

Eg | Melting point no .__ | _ (° C) _ 15; | 1-2 2-CH3-c (CH3) 3j oil | 1-3 4-CH- -C (CH -,) - | 117-19 3 3 3 t 20 1-4 4-Cl -C (CH3) 3 115-117 trans 1-5 2,4-Cl2 -C (CH3) 3 101-104 trans 1-6 4-Cl -C (CH3) 3 76-81 cis 17 71732

Preparation of the starting material used in Example 1: ci - - <=> -CH = CH-CC (CH3) 3 (II-1) 50-CH2 189 ml (2.0 mol) of dimethyl sulphate dissolved in 1200 ml of absolute acetonitrile are stirred at room temperature Dimethyl-10-sulfide dissolved in 162 ml (2.2 mol) dissolved in 400 ml of absolute acetonitrile. The reaction mixture is stirred at room temperature overnight. 118.8 g (2.2 mol) of sodium urea methylate are then added. After stirring for 30 minutes, 267 g (1.2 mol) of 1- (4-chloro-phenyl) -4,4-dimethyl-but-1-en-3-one in 600 ml are added dropwise over 30 minutes. absolute acetonitrile. The reaction mixture is stirred overnight.

The mixture is then evaporated, the residue is extracted with a mixture of water and ethyl acetate, the organic phase is collected, washed twice with water and once with saturated sodium chloride solution, dried over sodium sulfate, evaporated and the residue is distilled under reduced pressure. 2- (4-Chlorophenylphenyl) -2-tert-butyloxirane is obtained as a solid, m.p. 61-62.5 ° C.

In a similar manner, the following intermediates of formula (II) are obtained:

Table 2: / oVy-c-R (id

30 z. -XZJ o'-W

m

Eg YR Boiling point no ♦ ___ (° C) / mm H_ II-2 2,4-Cl2 -CH = CH- "35 II-3 4-ch3 -CH = CH-" 61 isolated II-4 4-F - CH = CH- "75 / 0.005 II-5 2 ~ CH3 -CH = CH-" 71-74 / 0.01 II-6 2,6-Cl2 -CH = CH- "18 717 3 2

The good efficacy of the substances according to the invention is evident from the following examples.

The following active ingredients are used in these examples: Compounds (A) C1 known from U.S. Patent 4,123,542. y-CH 2 CH 2 CH 3 C

10 = zS CH

r ^ 11 1 N- 15 (B) Cl-y-CH2-CH2-C-C4Hg-n f ^

OF

2 0 li "jj N_ii

Cl

/ OH

25 (C) Cl. M is N-CH2-CH2-C-CH3

CH

t 2

OF

Compounds known from N-11 30 DE 2654890

OOH

-CH-CH-C ^ Hg-n

I \ L

O

71 732 19 (E) C1 -..... ^ - CH-CH-CH2- ^ y ύ 5 compound known from DE-A-2736122

Cl (F, ct ^ jCaIrr / Λ-Χ!

10 - 'CH

r * -N>

Π I

N - and compounds of the invention 15

Ooh

—CH = CH-C-C (CH3) 3 - trans CH

(t

OF

OF

20 l-J

(m ^ 1 oh 25 e y - CH = CH-C-C (CH3) 3)

trans CH

T ^

U _JI

30 ^ Cl

/ —C? H

ci y — ch = ch-c-c (ch3) 3 (I) \ zzzJ trans CH ^ 35 ^ Nx

lf N

% _]] 20> —v oh 717 3 2 (J) CH —- V) .- CH = CH-C-C (CH3) 3 trans CH?

X

5 N_Il

Ooh ch = ch-c-c (ch3> 3

trans CH

f ^ (. "" Ή Ä_ji 15

/ F ~ \? H

(L) Cl - V> CH = CH-C-C (CH3) 3

'-' cis CH

20 is li] j

N _U

25 Example A

Sugar beet growth retardation Solvent: 30 parts by weight of dimethylformamide Emulsifier: 1 part by weight of polyoxyethylene sorbitol monolaurate 30 To make a suitable preparation, 1 part by weight of active ingredient is mixed with the given amounts of solvent and emulsifier and the desired amount of water is added.

Sugar beets are grown in a greenhouse when the cotyledons are fully developed. Once the plants have developed this far, they are sprayed with small amounts of preparations. After 14 days, the growth of the seedlings is measured at 21,71732 and the growth inhibition is calculated as a percentage of the growth of the control plants. 0% inhibition means similar growth as in control plants. 100% inhibition means a complete halt to growth.

5 The active substances, active substance concentrations and test results are shown in Table A below.

Table A

Slowing down the growth of sugar beet

Active substance_ Concentration,% Growth retardation,% = 0 (A) 0,05 0 (B) 0,05 5 15 (G) 0,05 27 +) + +) - leaf color dark green ++ ^ = thick leaves

20 Example B

Erysiphe test (barley) / preventive /

Solvent: 100 parts by weight of dimethylformamide

Emulsifier: 0.25 parts by weight of alkylaryl polyglycol ether To make a suitable preparation, 1 part by weight of active ingredient is mixed with the given amounts of solvent and emulsifier and diluted with the desired amount of water.

To test the preventive effect, 30 young plants are sprayed with the preparation wet. After drying of the spray liquid layer, the plants are infected with Erysiphe graminis f. Sp. hordei-itidillä.

The plants are transferred to a greenhouse at a temperature of 20 ° C and a relative humidity of 80% to promote the formation of hay fever.

7 days after infection, the results are checked.

22 71 732

The active substances, active substance concentrations and test results are shown in Table B below.

Table B

5 Erysiphe test (barley) / preventive

Active substance Active substance purity Cases of disease in spraying, compared to conceptual weight% plants,% 10 (D) 0.0025 58.7 (F) 0.0025 100 (A) 0.0025 100 (G) 0.0025 12.5 ( H) 0.0025 33.7 15 (I) 0.0025 8.7 (J) 0.0025 8.7 (K) 0.0025 12.5 (L) 0.0025 0.0

2 0 Example C

Erysiphe test (barley) / seed treatment The active substances are used as dry dressings. These are prepared by mixing the active ingredient used in each case with stone flour into a fine mixture which is evenly distributed on the surface of the seeds.

The seeds are covered by shaking for three minutes together with the pickling agent in a sealed glass bottle.

The standard soil mixture is sown with 3x12 seeds to a depth of 2 cm 30 cm. 7 days after sowing, when the seedlings have developed their first leaves, they are pollinated with Erysiphe graminis f. Sp. hordei spores.

The plants are placed in a greenhouse at a temperature of about 20 ° C and a relative humidity of about 80% to monitor the development of hay-35 mildew.

7 days after infection, the results are evaluated.

71732 23

The active substances, active substance concentrations and test results are shown in Table C below.

Table C

5 Erysiphe test (barley) / seed treatment

Active substance Amount of active substance Cases of disease in mg / kg of seeds on untreated plants,% 10 (D) 500 75.0 (F) 500 100 (A) 500 100 (E) 500 100 (J) 500 12.5 15 (K) 500 0.0 (L) 500 0.0

Example D

Sphaerotheca test (cucumber) / prophylactic 20 Solvent: 4.7 parts by weight acetone

Emulsifier: 0.3 part by weight of alkylaryl polyglycol ether

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

To investigate the preventive effect, the seedlings are completely sprayed with the active ingredient preparation. Once the rye-30 weft has dried, the plants are pollinated with conidia of the fungus Sphaerotheca fuliginea.

The plants are then grown in a greenhouse at 23-24 ° C with a relative humidity of about 75%.

35 10 days after infection, the results are evaluated.

24 71732

The active substances, active substance concentrations and test results are shown in Table D below.

Table D

5 Sphaerotheca test (throat) / prophylactic

Active substance Cases of disease (%) with active substance concentration _5 ppm_ 10 (D) 30 (H) 10 (I) 10 (J) 20 (K) 10 15 (L) 0

Example E

Venturia test (apple) / prophylactic Solvent: 4.7 parts by weight of acetone 20 Emulsifier: 0.3 parts by weight of alkylaryl polyglycol ether

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

To investigate the preventive effect, the young plants are sprayed with the active ingredient preparation completely wet. Once the syringe is dry, the plants are infected with an aqueous suspension of conidia of the apple scab (Venturia inaequalis) and left in the incubation chamber for 20 days at 20 ° C and 100% relative humidity.

The plants are then placed in a greenhouse at 20 ° C and a relative humidity of about 70%. Twelve days after infection, the results are evaluated.

35 The active substances, active substance concentrations and test results are shown in Table E below.

25 71 732

Table E

Venturia test (apple) / prophylactic

Active substance Cases of disease (%) at 5 active substance concentrations _______________ 1 ppm_ (E) 51

(C) SO

(B) 49 10 (G) 9 (L) 30 (I) 34

As can be seen from the experimental results presented above, the compounds according to the invention (the active ingredients GL used in the experiments) have clearly better plant growth-regulating and fungicidal properties than the structurally known DE-A-26 54 890 and DE 27 36 122 and the U.S. Pat. No. 4,123,542. (active substances AF used in the experiments).

Claims (5)

71732 26 Patent claims 1. 1-Hydroxyethylazole derivatives of the formula (I) 5 (C) YcH = CH-CR (I) z ch2 Ö characterized in that R is t-butyl, Z is chlorine, fluorine or methyl and m is 1 or 2 and their acid salts and metal salt comp. 2. For a 1-hydroxyethyl azole derivative of the formula 20 ° H (D VCH = CH'C'R (D Z / CH m i ^ rN- (l N N_il 25 color R is t-butyl, 30 Z chlorine, fluorine or methyl and myrrh 1 or 2, as the case may be a hydrogenation and metal salt complex, the reaction being carried out by means of an oxirane of formula 71732 30 ^ 0 ^) - CU sCH-CR (II) Zm ° ~ CH2 color SR, Z och m har ovan ang.Lvna betydelse, med azoler med formuleln H f 10 λΝ \ (III) fl N l! _3 15. föreningarna med formuleln (I) adderar en syra eller ett metallalt. 2. Method for the preparation of 1-hydroxyethylazole derivatives of formula (I) (J0 YcH = CH-C-R (I) i „2 m 'z 25 wherein R is t-butyl, Z is chlorine, fluorine or methyl and m is 1 or 2, and their acid salts and. for the preparation of metal salt complexes, characterized in that oxiranes of the formula (II) 71 732 2 7 (Q Vch = ch-c-r (id 7. \ _ y / \ Zm ° -CH2 in which R, Z and m are as defined above, react with azoles of formula (III), HT ίο l_u in the presence of a diluent and optionally a base, followed by the addition of an acid or a metal compound to the obtained compounds of formula (I). salt. 3. A compound for the treatment and fungicidal action of the compound (20), which comprises the preparation of a mineral and a 1-hydroxyethyl azole derivative with the formula (I) or a metal salt complex with a 1-hydroxyethyl azole derivative with the formula (I). 3. Plant growth regulators and fungicides, characterized in that they contain at least one 1-hydroxyethylazole derivative of the formula (I) or at least one acid salt or metal salt of a 1-hydroxyethylazole derivative of the formula (I). complex. 4. A process for the preparation of a mixture of 25 and 25 parts of a plant, including a 1-hydroxyethyl azole derivative according to formula (I), or a corresponding addition to a metal salt complex in a plant or other field, / eller deras livsrum. 4. A method for controlling plant growth and controlling fungi, characterized in that the plants and / or their growth medium or the fungi and / or their growth medium are treated with 1-hydroxyethyl azole derivatives of the formula (I) or their acid salts or metal salt complexes. 5. Use of acid salts and metal complexes of 1-hydroxyethylazole derivatives of the formula (I) and 1-hydroxyethylazole derivatives of the formula (I) for controlling plant growth and controlling fungi. Process for the preparation of plant growth regulators and fungicides, characterized in that 1-hydroxyethylazole derivatives of formula (I) or acid salts or metal-salt complexes of 1-hydroxyethylazole derivatives of formula (I) are mixed with media and / or surfactants. 29 Patent crude 7 i V 3 2 1. 1-hydroxyethyl azole derivative with the formula 5 / - \ ° H (O V-CH = CH-CR (I) CH2 m XT) butyl, Z is chlorine, fluorine or methyl and 15 m is 1 or 2, the same being a solid addition and a metal complex. 5. The preparation of a 1-hydroxyethyl azole derivative with the formula (I), respectively, with the addition of a metal complex of the 1-hydroxyethyl azole derivative with the formula (I), for the treatment of hydrogen, respectively.