CS241498B2 - Plant growth regulation agent and fungicide and active component production method - Google Patents

Abstract

Azole derivs. of formula (I), their acid addn. salts and metal salt complexes are new. R is alkyl or opt. substd. cycloalkyl or phenyl. X is nitrogen or CH. Y is OCH2, CH2CH2 or CH=CH. Z is halo, alkyl (opt. substd. by halo), cycloalkyl, alkoxy or alkylthio (both opt. substd. by halo) or opt. substd. phenyl, phenoxy, phenylalkyl or phenylalkoxy. m is 0-3. Also new are intermediates of formula (II). (I) are useful as fungicides (esp. against true mildews such as Erysiphe species and have both preventative and systemic actions and as plant-growth regulators. Typical responses include inhibiting vegetative growth of cereals etc., increasing sugar content of beet, and protein content of soya; stimulating latex flow in rubber trees; induction of parthenocarpic fruiting; breaking apical dominance, defoliation, acceleration of ripening; improving resistance to adverse climatic conditions etc. They are more effective than known cpds. such as 2-chloroethylphosphonic acid.

Description

The present invention relates to compositions for controlling the growth of plants and fungicidal compositions containing as active ingredient novel 1-hydroxyethylazole derivatives. Further. The invention 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 (cf. U.S. Pat. No. 3,156,554J). However, the efficacy of this substance, especially at low rates of application, is not always sufficient.

Furthermore, it is known that 2-chloroethylphosphonic acid has the ability to control plant growth (cf. DOS 1 667 968). Results achieved in. however, the use of this substance is not always satisfactory.

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

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

O ⁴ -C-CCCH-CR Zfa CH 2 O?

I. -

U) in which:

R is C 1 -C 4 alkyl, optionally alkyl. C 1 -C 2 -substituted C 3 -C 7 -cycloalkyl or optionally halogen and / or C 1 -C 4 -alkyl substituted phenyl;

X is nitrogen or -CH-,

Z is halogen, C1-C4alkyl, C1-C4alkoxy, C1-C4alkylthio, C1-C4haloalkyl of about 1 to 2 carbon atoms, up to 5 halogen atoms, haloalkoxy of 1 or 2 carbon atoms; 2 carbon atoms and 1 to 5 halogen atoms or optionally a halogen and / or (C1-C4) alkyl-substituted phenyl group; and m is 0, 1, 2 or 3, as well as their addition salts with hydrochloric acid or naphthalene; 1,5-disulfonic acid, which have the ability to control the growth of plants, and further have fungicidal activity.

The compounds of formula I have an asymmetric carbon atom and can therefore be formed in both optical isomeric forms. In addition, the compounds of formula I may exist in two geometric isomeric forms. The present invention relates to both mixtures of isomers and individual isomers.

According to the invention, the 1-hydroxyethylazole derivatives of the formula I are prepared by the production of oxiranes. of formula II

CH = CH-C (R) - CMp * (II) wherein

R, Z and m are as defined above, in reaction with the azoles of general interest. of formula III

in which

X is as hereinbefore defined, 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 formula I obtained.

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

Surprisingly, the 1-hydroxyazole 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 - as is well known - well active substances with the same type of action. Except. surprisingly, the compounds according to the invention 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-hydroxyethylazole derivatives of the present invention are generally defined by Formula I. In this formula, R is preferably a straight or branched (C 1 -C 4) alkyl group or a (C 1 -C 2) alkyl group substituted by a C 3 -C 7 cycloalkyl group and optionally a halogen and / or C 1 -C 4 alkyl substituted phenyl group. Z is preferably halogen, straight or branched (C 1 -C 4) alkyl, alkoxy and C 1 -C 4 alkylthio, haloalkyl and C 1 -C 2 haloalkoxy, with 1 to 5 identical or different halogen atoms , in particular fluorine and chlorine atoms, and in each case optionally a halogen and / or C1-C4-alkyl-substituted phenyl, X and m are preferably as defined under formula I.

Particularly preferred are those compounds of formula (I) wherein:

R is tert-butyl, isopropyl or methyl, in each case optionally substituted by methyl, cyclopropyl, cyclopentyl or cyclohexyl. as well as optionally one or two identical or different fluorine, chlorine or methyl-substituted phenyl groups,

Z represents fluoro, chloro, bromo, methyl, tert-butyl, methoxy, methylthio, trifluoromethyl, trifluoromethoxy, and optionally once or. twice, the same or different fluorine, chlorine and / or methyl substituted phenyl, and

X and m 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 general formula may be mentioned. formula I:

Table 1

Zin

-C (CH ₃ ) ₃

_3,4-Cl2

4-CF ₃

4-OCF ₃

4-SCH3

4-C (CH3) ₃

-C (CH ₃ ) ₃

-С [СН ₃₎ з -C (CH3) _3, -C (CH _{3) 3}

-С (СНз) ₃

_3,4-Cl2

4-CF 3

4-OCF ₃

4-SCH3

4-C (CH3) ₃

XŠ> - ^CI а

-CH (CH _{3] 2}

N (CH)

N (CH)

N (CH)

N (CH)

N (CH)

N (CH)

N (CH)

N (CH)

N (CH)

N (CH)

N (CH)

N (CH)

N (CH)

N (CH)

N (CH)

N (CH)

_3,4-Cl2

4-CF ₃

4-OCF ₃

4-SCH ₃

4-SCH ₃

N (CH)

N (CH)

N (CH)

N (CH)

N (CH) CH _{(CH3) 2}

-СН (СН ₃ ) ₂ —СН (СН ₃ ) ₂ —СН (СН ₃ ) ₂ —СН (СН ₃ ) ₂

-СН (СН ₃ ) ₂

R

X

)Е) ЧЕ) ЧЕ) ЧЕ) ЧЕ) -0 ЧЕ) 0 сн ₃

₃

Ί <1 ^{сн з} сн 0 ₃ 0 ₃ 0 сн сн ₃ -СН (СН,) _г -СН (СН,) _г -СН (СН _{3) 2} 0 ЧЕ) ЧЕ)

N (CH)

N (CH)

N (CH)

N (CH)

N (CH)

N (CH)

N (CH)

N (CH)

N (CH)

N (CH)

N (CH)

N (CH)

N (CH) '

N (CH)

N (CH)

N (CH)

N (CH)

N (CH)

N (CH)

N (CH)

X ^Z m

4-C1

R _o

CH ₃

N (CH)

4-F

O

CH ₃

N (CH)

4-CH3 - 1 ^ ·. CH ₃ N (CH) 2,4-Cl2 -С (СНз) ₃ N [CH) 4-CH3 -С (СНз) ₃ N (CH) 4-C1, 2-CH 2.) -С (СНз) з N (CH) 4-F -С (СНз) з N

If, for example, 2- (4-chlorophenylethenyl) -2-tert-butyloxirane and 1,2,4-triazole are used as starting materials, the illustrate the actions of the invention by the following reaction scheme:

The oxiranes used in the process of the invention as starting materials are generally defined by Formula II. In this formula, the symbols R, Z and the index m preferably have the meanings already given in relation to the description of the compounds of the formula I for these substituents and the index m as preferred.

The compounds of formula II are novel. The preparation of these compounds is described in U.S. Pat. No. 241 500.

The azoles which are additionally used as starting materials in the process according to the invention are generally defined by formula III. In this formula, X is preferably those already mentioned in the definition of these substituents for compounds of formula I as being preferred for these substituents.

The azoles of formula III are generally known compounds 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 methoxvethanol, ketones such as 2-butanone, nitriles such as acetonitrile, esters such as ethyl acetate ^1, 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 alclamines. cycloalkylamines and aralkylamines, in particular triethylamine.

The reaction temperatures may vary within wide limits when carrying out the process of 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 carrying out the process according to the invention, preferably 1 to 2 mol of azole 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 acid or with naphthalene-1,5-disulfonic acid.

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 or naphthalene-1,5-disulfonic acid, and may be isolated in a known manner. 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 roadside, airports and orchards can be reduced. 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.

It is also important to use 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 cause grain stalks to strengthen, 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 the need to worry about crop lodging.

The suppression of vegetative growth allows many crops to denser or plant 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 plant growth 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.

Stimulators of vegetative growth can also often be achieved with growth regulators. This is of great importance when vegetative parts of plants are harvested. However, stimulation of vegetative growth can also simultaneously 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 fruit or to increase the protein content of soy or grain. Furthermore, it is also possible, by means of growth regulators, to inhibit the degradation of desired substances contained in plants, such as sugar in sugar beet or sugar cane, 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. It is also possible to achieve pollen sterility, which is of great importance in the breeding and production of hybrid seeds.

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 very desirable, especially in the cultivation of ornamental plants, even 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 substances 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 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 transpiration of the plants prior to transplanting.

Growth regulators can also be used to 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 “chemical thinning” in order to break the so-called “alternative”. An alternative is the special behavior of some fruits, based on endogenous, very different yields from year to year. Growth regulators can also serve to reduce the force required for harvesting fruit at harvest time so that mechanical harvesting or manual harvesting is facilitated.

By means of growth regulators, it is furthermore possible to accelerate or slow down the ripening of the harvested products before or after harvesting. This is particularly advantageous since optimum adaptation to market requirements can be achieved.

Furthermore, growth regulators can in many cases serve to improve the coloring of the fruit. In addition, the 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 plants to be able to carry out fully mechanical or manual harvesting in only one working stage.

The use of growth regulators can also affect seed or bud rest periods, ie endogenous annual rhythm, so plants such as pineapple or horticultural ornamental plants germinate, sprout or bloom when they would not germinate, sprout or sprout under normal conditions. . nekvetly.

Delayed bud growth or delayed germination of the seeds can also be achieved by growth regulators, for example, to prevent damage caused by under frost in colder climate areas.

Finally, frost, drought or high salt content in the soil can be induced by the growth regulators in the plants, allowing 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.

Fungicides are used in plant protection to combat fungi of the classes Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.

Since the plants of the active compound according to the invention are well tolerated at the concentrations required for combating fungal diseases of the plants, these compounds can be used for the treatment of aboveground parts of plants, seedlings and seeds, and 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 the origin of powdery mildew or Erisiphe graminis.

It is particularly advantageous that the active compounds according to the invention not only have a projective effect but are also systemically active, which makes it possible to protect the plants against fungal infections 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 a 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. . If water is used as a filler, it is possible; organic solvents, for example, can also be used as co-solvents. Basically suitable liquid solvents are: aromatics such as xylene, toluene or alkyl naphthalenes, 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, as well as their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, 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. .d lignin, sulphite waste liquors and methylcellulose.

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

Further, these compositions may contain colorants such as inorganic pigments, for example iron oxide, titanium dioxide and ferrocyanide blue, and organic colorants, such as alizarin dyes and metallic azo-phthalocyanine dyes, as well as trace elements, for example 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, for example, 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 dosage forms prepared therefrom, such as ready-to-use solutions, emulsifiable concentrates, emulsions, foams, suspensions, wettable powders, pastes, soluble powders, dusts and granules. The application is carried out in the usual manner, for example by watering, spraying, spraying, spraying or spraying. by spreading, dusting, foam, painting, etc.

Further, it is possible to administer the active compounds by the so-called ULV method or to inject the active compound into the soil. It is also possible to treat the seeds of the plants.

When the compounds of 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 compound are used per 1 ha of soil 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 parts of plants varies between 1 and 0.0001% by weight, preferably between 0.5 and 0.001% by weight, in the use forms. In the treatment of seed, an amount of active compound of from 0.001 to 50 g per kg of seed is generally required, preferably of from 0.01 to 10 g per kg of seed. 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 i 1-1)

OH

C (CH3) ₃

A solution of 17.75 g (0.075 mol) of 2- (4-chlorophenylethenyl) -2-tert-butyloxirane and 6.8 g (0.1 mol) of imidazole in 30 ml of ethanol was heated at 150 ° C for 20 hours. The reaction mixture was concentrated and the crystalline residue was triturated with ether, and the solid was then filtered and recrystallized from acetonitrile to give 1- (4-chlorophenyl) -4,4-dimethyl-3- (imidazolylmethyl). 1-penten-3-ol having a melting point of 158.5 to 162 degrees Celsius.

Preparation of the starting material

CH = CH-C- CH 2 -) »/ \

O — CH _Z (Il ~ 1)

A solution of 162 ml (2.2 mol of dimethylsulfide) in 400 ml of absolute acetonitrile was added to a solution of 189 ml (2.0 mol) of dimethyl sulfate in 1200 ml of absolute actonitrile at room temperature. 118.8 g (2.2 mol) of sodium methoxide are then added and the mixture is stirred for 30 minutes and then a solution of 267 g (1.2 mol) of 1- (4-chlorophenyl) -4,4 is added dropwise over 30 minutes. Dimethylbut-1-en-3-one in 600 ml of absolute acetonitrile The reaction mixture is then stirred overnight, then the reaction mixture is concentrated and the residue is partitioned between water and ethyl acetate, the organic phase is separated, washed twice with water and once It is washed with saturated sodium chloride solution, dried over sodium sulphate and concentrated, and the residue is distilled under vacuum.

2414S8

2- (4-chlorfenylethenyl) -2-terc.butyloxiran _e of melting point 61 DEG-62.5 DEG.

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

Table 2 example number

melting point (° C)

I— 2 _2-CH3 N 149—150 AND- 3 4-F CH 144—146 AND- 4 2-CH3 CH 127—132 AND- 5 4-СНэ N 117—119 AND- • 6 4-СНз CH 144—146 AND-  7 2.6-С1 ₂ CH 110—116 AND- 8 4-F N 129—131 AND- 9 4-C1 N 115-117 trans form AND- 10 2-C1 N 146—147 AND- 11 2,4-Cl ₂ N 101—104 AND- 12 4-C1 N 76-81 cis-form

The following starting materials were obtained in an analogous manner to that described in the Example.

of formula II (CH3) ₃ Zm. Q — CH _Z (li)

Example number · Z _m Boiling point (° C / Pa)

II — 2 2,5-Cl ₂ product not insulated II — 3 _4-CH3 product not insulated II — 4 4-F 75 / 0.7 Pa II — 5 2-CH ₄ 71—74 / 1.3 Pa II — 6 2,6-Cl ₂ product not insulated

Examples illustrating biological activity

Example A

Growth inhibition solvent beet:

parts by weight of dimethylformamide emulsifier:

part by weight of polyoxyethylene sorbitan monolaurate

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 mixture is made up to the desired concentration with water.

Sugar beet plants are grown in the greenhouse until the cotyledons are fully developed. At this stage, the plants are sprayed until dripping with active agents. After 14 days, the growth of the plants is measured and the growth retardation is calculated as a percentage of the growth of the controls of 24148 of these plants. At the same time, 0% inhibition of growth means a condition corresponding to that of the control plants, 100% inhibition of growth means that the plants no longer grow.

Table A

Sugar beet growth inhibition active compound control of known substance:

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

concentration in% growth inhibition in% _ _ __

0.05 0 (U.S. Pat. No. 4,123,542)

0.05 (U.S. Pat. No. 4,123,542) Compounds of the invention:

0.05

27 *) **) * 'intensely green leaves

7) thick leaves

Example Β

Test for Erysiphe graminis (protective effect) barley solvent:

100 parts by weight of dimethylformamide emulsifier:

0.25 part by weight of alkylaryl polyglycol ether

To prepare a suitable active ingredient, 1 part by weight of the 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 efficacy, mlaTab ulk and B longer test plants were 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 kept 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.

Table B summarizes the results obtained, the test compounds and the concentration of test substances used.

Test for Erysiphe graminis (protective effect) barley test compound concentration effective degree of infestation in% substance in spray untreated control suspension in% wt.

known substances:

(DE-OS 26 54 890)

0,0025

58.7

0,0025

100 (DE-OS 27 36 122)

0,0025

100 (U.S. Pat. No. 4123,542) test compound concentration of the active ingredient in the spray suspension in% w / w.

degree of infestation in% of untreated control

Compounds of the invention:

OH _ct _J ~~ \ _ _CHsC HCC (CH ₃ ) ₃ "trans CH ₂ ^С / ^ OH ^ ^ CH CH (CH ₃ ) ₃ trans čw _z

0,0025

0,0025

12.5

33.7

AND

N · -

OH

AND

CH = CH-CC (CH ₃ ) ₃ trans CH ₃ · A · OH

CH 2 CH 2 CH-CH (CC ₃ ) ₃ trans?

0,0025

0,0025

8.7

8.7

ClS

0,0025

0,0025

12.5

Example C

Test for Erysiphe gramínis f. Sp. hordei (barley / seed treatment)

The active compounds are used in the form of a dry mordant. This is prepared by thoroughly mixing the active ingredient with the ground mineral to give a fine powder mixture which ensures perfect distribution of the active ingredient on the seed surface.

The application is carried out by shaking the seeds in a closed glass staining bottle for 3 minutes.

The barley seed is then sown 2 cm deep into standard soil (3 x 12 grains). 7 days after sowing, when young plants develop their first leaf, they are dusted with spores of Erysiphe graminis f. Sp. hordei.

The plants are placed in a greenhouse where they are stored at a temperature of about 20 ° C and a relative air humidity of about 80% to create favorable conditions for the development of powdery mildew piles.

The experiment is evaluated 7 days after the infestation.

The following Table C contains test results including test compound data and concentrations.

Table C

Test for Erysiphe gramínis f. Sp. hordei (barley) / seed treatment of test compound amount of active substance in mg / kg seed infestation in% untreated control of known substance:

OH

500

75.0 (DE-OS 26 54 890)

CHo I

500

100 (DE-OS 27 36 122)

500

100 (U.S. Pat. No. 4123,542) test compounds amount of active ingredient in mg / kg seed infestation% of untreated control

500

100 (DE-OS 26 54 870)

Compounds of the invention:

OH сн ₃ - ^ = сн сн4-с (CH3) ₃

500

12.5

OH

Q-CH - CH-CC (CH3) ₃ trans _СН г

500

0.0

OH

Cl-CH-CH-CC (CH ₃ cis _S J 0

Example D

Powdery mildew test (Sphaerotheca fuliginea (cucumber) / protective effect solvent:

4.7 parts by weight of acetone emulsifier:

0.3 part by weight of alkylaryl polyglycol ether

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 concentrate is diluted with water to the desired concentration.

In order to determine the protective effect, the young plants are sprayed with the active agent up to the wetting stage. After the spray layer has dried, the plants are dusted with conidia of Sphaerotheca fuliginea.

The plants are then placed in a greenhouse at 23-24 ° C and 75% relative humidity. The test is evaluated 10 days after inoculation.

The following Table D contains test compound data, concentrations, and results.

Table. D

Powdery mildew test (Sphaerotheca fuliginea) (cucumber) / protective effect test compounds % damage at 5 ppm drug concentration

known substance:

Cl

(DE-OS 26 54 890) of the compounds according to the invention:

_0] H CH ^S CH-CC (CH ₃ J ₃ I trans CH _{0 a}

trance

OH

CH = CH-C (CH ₃ ) ₃ trans CH ₂

241498 23 24 test compounds % damage at 5 ppm drug concentration

Example E

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

4.7 parts by weight of acetone emulsifier:

0.3 part by weight of alkylaryl polyglycol ether

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

In order to test the protective effect

In Table E, the young plants are sprayed with the active agent up to the wetting stage. After the spray coat has dried, the plants are inoculated with an aqueous suspension of the apple scab (Venturia inaequalis) and then left in the incubation chamber for 1 day at 20 °. ° C and at 100% relative humidity.

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

Evaluation is performed 12 days after inoculation.

Table E lists the test compounds, test compound concentrations, and results obtained.

Test for apple scab (Venturia inaequalis) (spring) / protective effect of test compound infestation in% at active substance concentration of 1 ppm known substance:

OH

(DE-OS 26 54 890)

(U.S. Pat. No. 4123,542) of the test compound attacked in% i at an active compound concentration of 1 ppm

(U.S. Pat. No. 4,123,542) compounds of the invention:

OH

CI-Q-CH - CH-CC (CH3) ₃

Claims (2)

A plant growth regulating agent and a fungicidal agent, characterized in that it contains as active ingredient at least one 1-hydroxyethylazole derivative of the general formula I (1) in which: R is C1 -C4 alkyl, optionally C1 -C4 alkyl substituted C3 -C7 cycloalkyl or optionally halogen and / or C1 -C4 alkyl substituted phenyl, X represents a nitrogen atom or a —CH— group, Z is halogen, C1 -C4 alkyl, C1 -C4 alkoxy, C1 -C4 alkylthio, C1 -C4 haloalkyl, C1 -C5 haloalkyl, C1 -C4 haloalkoxy; 2 carbon atoms with 1 to 5 halogen atoms or optionally a halogen and / or (C1-C4) alkyl substituted phenyl group; , 5-disulfonic acid, 2. A method for producing an active ingredient according to claim 1, formula I, characterized in that the oxirane of the formula II ^ -CH = CR ^Z fn. O — CH _Z (II) wherein R, Z and m have the meanings given in 1, act on the azoles of formula III (III) Ί H in which X is as defined in point 1, in the presence of a diluent and optionally in the presence of a base, whereupon optionally obtained compounds of formula I are added with hydrochloric acid or naphthalene-1,5-disulfonic acid.