DD208295A5 - PLANT GROWTH REGULATING AND FUNGICIDAL AGENTS - Google Patents

Abstract

1. Azolyl-alkenones and -ols of the formula see diagramm : EP0079006,P19,F1 in which R**1 represents the grouping see diagramm : EP0079006,P19,F2 in which Z**1 and Z**2 are identical or different and represent hydrogen, halogen or alkyl with 1 to 4 carbon atoms, and, furthermore, R**1 represents phenyl which can be mono- or polysubstituted by identical or different substituents selected from halogen, alkyl with 1 to 4 carbon atoms, alkoxy and alkylthio each with 1 to 4 carbon atoms, alkyl- and dialkylamino each with 1 to 4 carbon atoms in each alkyl part, and also halogenoalkyl, halogenoalkoxy and halogenoalkylthio each with 1 to 2 carbon atoms and 1 to 5 identical or different halogen atoms, phenyl and/or phenoxy, it being possible for the two last-mentioned radicals in turn to be substituted by halogen and/or alkyl with 1 to 2 carbon atoms, R**2 represents straight-chain or branched alkyl with 1 to 12 carbon atoms, and also phenyl which can be mono- or polysubstituted by identical or different substitutents selected from halogen, alkyl with 1 to 4 carbon atoms, alkoxy and alkylthio each with 1 to 4 carbon atoms, alkyl- and dialkylamino each with 1 to 4 carbon atoms in each alkyl part, and also halogenoalkyl, halogenoalkoxy and halogenoalkylthio each with 1 to 2 carbon atoms and 1 to 5 identical or different halogen atoms, phenyl and/or phenoxy, it being possible for the two last-mentioned radicals in turn to be substituted by halogen and/or alkyl with 1 to 2 carbon atoms, or R**2 represents cycloalkyl which has 3 to 7 carbon atoms and is optionally substituted by halogen and/or alkyl with 1 to 4 carbon atoms or cycloalkylalkyl which has 3 to 7 carbon atoms in the cycloalkyl part and 1 to 2 carbon atoms in the alkyl part and is optionally substituted by halogen and/or alkyl with 1 to 4 carbon atoms, X represents the CO or CH(OH) group and Y represents a nitrogen atom or the CH group, and acid addition salts and metal salt complexes thereof.

Description

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Plant growth regulating period and fungicidal agents Field of application of the invention

The invention relates to novel plant growth regulating and fungicidal compositions based on τοπ azolyl alkenoms and oils, which can be used successfully in agriculture. ,

Known technical solutions

It has already been disclosed that certain β, 6-disubstituted 2,2-dimethyl-4 '(1 * 2 ₎ 4-triazol-1-yl) -5-lipene-3-ones and oils are good plant growth regulating and fungicidal agents. Have properties (see DE-OS 29 05 981), However, the effect of these compounds, especially at low application rates and concentrations, not always fully satisfactory »

Aim of the invention

The aim of the invention is to eliminate these disadvantages »

Essence of the invention

The invention is based on the task of providing new plant regulators and fungicides »

According to the invention these are the new asolyl-alkenones and oils of the formula. '

Λ O

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in which

R is alkyl, haloalkyl or optionally substituted phenyl,. ,

2 R is alkyl, optionally substituted phenyl, optionally substituted cycloalkyl or optionally substituted Gycloalkylalkyi,

is the CO or GH (OH) group and Y is a nitrogen atom or the CH group,

and their acid addition salts and Me lisa lz complexes found,. ,

The compounds of the formula '(.1)' according to the invention come in the geometric. Isomers E (trans) and Z (ice) are present, in the E, Z-ITomenklatür the ar. ' the double bond substituents according to the Cahn-Ingold-Prelog rule according to decreasing priority-arranged. If the preferred substituents are on the same side of the double bond, the configuration .Z- (derived from - "together") is present; if they are on opposite sides, the configuration Ξ (derived from "opposite") exists.

In addition, the compounds of the formula (I) according to the invention have I = CH (OH) 3T / ei; Asj-metric carbon atoms they can then be present in the two geometric isomers (three-and erythro-pom), which can be produced in different proportions. In both cases they are present as optical isomers.

~ ii C 1 /

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Furthermore, it has been found that the Äzolyl-alkenones and oils of the formula (I) and their acid addition salts and metal salt complexes obtained when compounds.der formula

R ¹ - CO - C = CH - CH ₂ - R ² (II),

JLJ

in which

R, R and Y are as defined above.

in the presence of a diluent and optionally in the presence of a catalyst or, in the presence of alumina, and optionally the obtained thereby obtained inventive azolyl-alkenones of the formula

R ¹ -CO-CH-CH = CH-R ² (Ia),

in which

E ", R and Y have the meaning given above, in a generally customary manner'reduziert and optionally subsequently added to the thus obtained compounds of the formula (I) an acid or a metal salt.

Finally, it has been found that the new Äzolyl alkenones and oils of the formula (I) and / or their acid addition Salza and Metallsaiz Kompliese have strong pflansenwachstumsregulierende- and strong fungisi.de properties.

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In addition, the new azolyl-alkenones and oils of the formula (I) are interesting intermediates for the preparation of other crop protection agents.

In the case of the keto derivatives, the keto group can be reduced to a --CH (OH) - group or a --CR (OH) - group. Furthermore, functional derivatives of the keto group can be obtained by appropriate reactions, such as. B, oximes and oxime ethers, hydrazones and ketals. The carbinol derivatives can be converted to the hydroxyl group in the usual way in the corresponding ether. Furthermore, by reaction with z. Bt acyl halides or carbamoyl chlorides in a manner known in principle acyl or carbamoyl derivatives of the compounds of formula (I) can be obtained »

Surprisingly, the erfzuidungsgemaßen compounds have a better plant growth regulating and fungicidal action than those known from the prior art 6,6-disubstituted _2} 2-Dimethy1-4- (1,2,4-triazol-1-yl) -5-he3: en-3-ones and oils which are chemically and functionally obvious compounds. The erfindungsgernäßen agents scheller. thus an enrichment of the technology,

The azolyl alkenones and oils according to the invention are generally defined by the formula (I)

QTT 21 preferably i ^A '2

R for dfe grouping -C-CH ^, where.

Z ¹ and S "are identical or different and represent hydrogen, halogen or alkyl having 1 to 4 carbon atoms, that is optionally phenyl which is monosubstituted or polysubstituted, preferably being mentioned as substituents: halogen alkyl having 1 to 4 carbon atoms -

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atoms, alkoxy and alkylthio having in each case 1 to 4 carbon atoms, alkyl and dialkylamino having at least 1 to 4 carbon atoms in each alkyl moiety, furthermore halogenoalkyl, haloalkoxy and haloalkylthio each having 1 to 2 carbon atoms and 1 to 5 identical or different halogen atoms, as Pluor- and chlorine atoms, and optionally substituted by halogen or alkyl having 1 to 2 carbon atoms substituted phenyl and phenoxy;

ο Pl is straight-chain or branched alkyl having 1 to 12 carbon atoms; for optionally mono- or polysubstituted by identical or different substituents phenyl, preferably being mentioned as substituents: halogen, alkyl having 1 to 4 carbon atoms, alkoxy and alkylthio each having 1 to 4 carbon atoms, alkyl and Diaikylanino each having 1 to 4 carbon atoms in each Alkyiteil , furthermore haloalkyl, haloalkoxy and haloalkylthio having in each case 1 to 2 carbon atoms and 1 to 5 identical or different halogen atoms, such as fluoro and chloro atoms, as well as phenyl optionally substituted by halogen or alkyl having 1 to 2 carbon atoms and "phenoxy;

R preferably represents optionally mono- or polysubstituted, identically or differently substituted cycloalkyl or cycloalkylalkyl having in each case 3 to 7 carbon atoms in the cycicalkyl moiety and 1 to 2 carbon atoms per alkyl moiety, preference being given to alkyl substituents: alkyl having 1 to 4 carbon atoms and halogen,

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Σ for the GO or CH (OH) group and

Y is a nitrogen atom or the CH group.

Particular preference is given to those "compounds of the formula (I) in which

CH ₂ Z

R is the moiety -C-GH ^, where

CH ₉ Z ²

12

Z and Z are the same or different and are responsible for

or butyl;

and optionally unsubstituted or trisubstituted by identical or different substituents, and / or which are mentioned as substituents: fluorine, chlorine, methyl, isopropyl-tert-butyl, methoxy, methylthio, isopropoxy, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, Methyl amino, Dime thy laniinöj and optionally substituted by fluorine, chlorine or methyl

for straight chain. or branched alkyl · with 1 to S

Altes

Carbon atoms; furthermore represents optionally monosubstituted to trisubstituted, identically or differently substituted phenyl, where the substituents mentioned are: fluorine, chlorine, methyl, isopropyl, tert -

meth.ylarnino ₃ and if necessary through. ? luor ₅ Kethyl chlorine or substituted phenyl and \ phenoxy; and

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2 R furthermore represents in each case α-aryl methyl, ethyl, isopropyl, fluorine or chlorine-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl;

Σ represents the CO or CH (OH) group and

Y stands for a nitrogen a.tom or the CH group *

Specifically, in addition to the compounds mentioned in the preparation examples, the following compounds of the general formula (I) may be mentioned (where I is the CO or CH (CH.sub.2) group and Y is a nitrogen atom or the CH group):

U6 U

Table 1

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R ¹ --X - CH - CH = CH - R ² (D.

ⁿ 3 ^G 1 CH CH ₂ -CHCCH ₃ )

CH ₂ Cl

H-C-C

CH ₂ Cl -CH ^ -CH (CHO,

C-

₃ C

/ * ptl ^ η ΧΙ Λ1

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Table 1 (continued) E ¹

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-CH ₂ -CHC

-CH ₂ -CH (CH.

CH,

CH,

H (CH ₃ ) -CH (CH ₂ )

(CH ₃ ).

(GH.). C

-C (CH ₂ ) ₂ -CH (CH.) Ρ

-3

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Table 1 (continued)

(CH ₃ V ₃ C-

(CH ₃ ) ₃ C-

Cl

rf]

Cl

H ₃ C

CH,

iio J 3 ^

CP

Cl

GH

(CH ₃ O ₃ C-

^ ₃

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Preferred compounds of the invention are also addition products of acids and those azolyl-alkenones

-ι ρ and oils of the Pormel (I) - in which R ', E, I and Y have the meanings which have already been mentioned as preferred for these radicals «

The acids which can be adducted preferably include hydrohalic acids, such as _e B »acid, hydrochloric and hydrobromic acid, in particular hydrochloric acid, furthermore phosphoric acid, nitric acid, sulfuric acid, mono- and bifunl-ctioneile carboxylic acids and hydroxycarboxylic acids, such. B, acetic acid, maleic acid,. Succinic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid and lactic acid, as well as sulfonic acids, such as a * B, p-toluenesulfonic acid and 1,5- ^ aphthalindisulfonsäure.

In addition, preferred compounds of the invention are addi- tion products of salts of metals of the II to IV * "main and I, and II, as well as TV, to VIII." Uebengruppe and those 'Azol5 ^r l-alkenones and oils, the formula ( I), in which

R, R -, X and Y are the meanings have been called wise for these radicals,

1 2 R, R -, X and Y have the meanings that are already preferred

Salts of copper, sinks, manganese, magnesium, tin, iron and titanium are particularly preferred as anions of these salts are those which are derived from those acids which lead to physiologically acceptable Additicnsprodukten * Particularly preferred such acids In this connection, bind the polyhydric acids, such as hydrochloric and hydrobromic acids, as well as phosphoric acid, nitric acid and sulfuric acid. "

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For example, using 6-cyclohexyl-2,2-aimetyl-4- (1,2,4-triazol-1-yl) -4-hexen-3-one as a starting material, alumina as a reactant and methanol as a diluent, the Reaction process by the process according to the invention by the following Scheme are reproduced:

(CE,) - C-CO-C = CH-CE ₀ - H .33 j 2

Al ₂ O ₃ ZCH ₃ OH

(CE ₃ J ₃ C-CO-CH-CH = CH -

If, for example, 6-cyclohexyl-2,2-dimethyl-4- (1,2,4-tria2ol-1-yl) -5-hesen-3-one is used as starting material and sodium borohydride as reducing agent *, the course of the reaction can be determined according to according to the invention by the following Formula!

CCH -) - C-CO-CH-CE = CH-H

HaBH ₁

X-MS _n . (CHO) ο C-CH-CH-CH = CH

f 2 ^{3 3} "i

The compounds required as starting materials in carrying out the process according to the invention are characterized by

Formula (II) generally defined. In this formula, 1

1 ρ. ,

R ', R ~ and Y preferably those meanings that

~ and Y preferably those meaning already in connection with the description of erfindungsgemäi3en substances of formula (I). preferably for these sub-constituents' called me the.

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The compounds of the formula (II) are known or can be prepared in a simple manner by processes known in principle (cf., DE-OS 30 00 643 and the literature cited therein), thus obtaining compounds of the formula (II) in which one's ketoenamine the formula

R ¹ - CO - G = CH - Έ ^ (III), t \ 4

in which

^R "and Y have the abovementioned meaning and

Λ J

R ^ and R 'are the same or different and

for 'alkyl having 1 to 4 carbon atoms, in particular. Methyl, stand,

with magnesian-organic compounds of the formula

in 7 / elcher

> 2

Shark for halogen stand

R has the meaning given above and.

in the presence of an inert organic solvent, such as, for example, ether, and optionally in the presence of an inert gas, such as nitrogen, at temperatures between -20 and 120 ⁰ C _: (see also DB-OS 30 00 643 and the preparation examples) *

The Iietoenamines of the formula (III) are known or can be easily prepared by the process known in the art

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(see DS-OS 30 00 643). Thus, ketoarenes of the formula (III) are obtained by reacting ascoly ketones of the formula

R ¹ - CO - CH ₂ - ET j (V),

in which

R and Y are as defined above,

with amide acetals or aminal esters of the formulas

R ³

_R 4

(Via)

(VIb) ₃

IR ³ R ⁴

in which

3 A

R and R 'have the meaning given above

and

R ⁵ . is alkyl having 1 to 4 carbon atoms,

in a manner known per se in the presence of an inert organic solvent, such as an aromatic hydrocarbon and as. in particular, an amide acetal or "aminal ester of the formula (VIa) or" (VIb) used in excess at boiling heat

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(See also Chem. 3, 101 , 41-50 (1968); J. Org. Chem. 42, 4248-50 (1978) and the preparation examples).

The asoly! Ketones of the formula (V) are known (compare, for example, DE-OS 24 31 407, DS-OS 26 10 022 and DE-OS 26 38 470) or can be prepared by customary methods, by reacting the corresponding halogen ketones in the presence of an acid binder with 1,2,4-triazole or imidazole »

The amide acetals or aminal esters of the formulas (YIa) or, (YIb) are generally known compounds of organic chemistry (compare, for example, 3, Chem, Ber, 101 , 41-50 (1968) 'and J. Org. Chem , 43, 4243-50 (1978)) »

The organomagnesium compounds of the formula (IY) are generally known compounds of organic chemistry »

Suitable diluents for the process according to the invention for the preparation of the asolyl-alkenones of the formula (Ia) are organic solvents which are inert under the reaction conditions. These include, preferably, ketones, such as acetone and methyl ethyl ketone; Alcohols> such as methanol, ethanol or isopropanol; aliphatic and aromatic hydrocarbons, such as benzene, toluene or xylene; as well as halogenated ^; Hydrocarbons, such as methylene chloride, carbon tetrachloride, chloroform or chlorobenzene * _r .

The process according to the invention for the preparation of the asolylalkene shades of the formula (Ia) is optionally used in the presence of

? 7rid ± / i ₃ triethylamine and "TjIT-dimethyl-oansylamiii"

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The reaction temperatures can your Verfaiiren invention for the preparation of azolyl-alkenones of the Pormal (Ia) can be varied within a substantial range · in general carried out at temperatures between 30 · lind 150 ⁰ C, preferably between 50 and 120 ⁰ C,

The procedure according to the invention for the preparation of the azolyl-alkenones of the formula (Ia) is carried out either purely thermally by heating the compounds of the formula (II) or by base catalysis, with 0.1 to 1 of 1 mol of the compounds of the formula (II) being Mol of base is used, or in the presence of aluminum oxide «The isolation of the compounds of the invention is carried out in all cases in the usual manner *

The reduction according to the invention for the preparation of the Azolylalkenole of formula (I) in a conventional manner, z _e 3, by reacting asolyl alkenones of the formula (Ia) with complex hybrids, if appropriate in the presence of a diluent, or by reaction of azolylalkene of the formula (Ia) with aluminum isopropylate in the presence of a diluent,

When working with complex hydrides, come as a diluent for this reaction according to the invention polar organic solvents, in. Question, These include preferably alcohols, such as methanol, ethanol, butanol, isopropanol and ethers, such as diethyl ether or tetrahydrofuran * The reaction is generally 0 to 30 C, preferably carried out at 0 to 20 ⁰ C, For this purpose, is used for 1 mol of the ketone of the formula (Ia) about 1 reaction equivalent of a complex hydride, such as 3atrium borohydride or lithium alanate, a. To isolate the reduced compounds of formula (I) '

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the residue taken up in dilute hydrochloric acid, then made alkaline and extracted with an organic solvent. The further workup is carried out in the usual way,

When working with aluminum isopropylate, suitable diluents for this reaction according to the invention are preferably alcohols, such as isopropanol, or inert hydrocarbons, such as benzene, in embossing. The reaction temperatures can in turn be varied within a substantial range; In general, one operates between 20 and 120 C, preferably at 50 to 100 ⁰ C, to carry out the reaction is used for 1 mol of the ketone of formula (Ia) about 1 to 2 moles of aluminum isopropoxide. In order to isolate the reduced compounds of the formula (I), the excess solvent is removed by distillation in vacuo and the resulting aluminum compound is treated with dilute sulfuric acid or sodium hydroxide solution. The further work-up is carried out in the customary manner.

For the preparation of acid addition salts of the Azolyi alkenons and oils of the formula (I) are preferably those acids in question, which have already been mentioned in connection with the description of Säureadditicns-Salse according to the invention as preferred acids.

The acid addition salts of the compounds of the formula (I) can be prepared in a simple manner by customary salt formation methods, examples _{9 to} 3, by dissolving a compound of the formula (1) in a suitable inert solvent and adding the. Acid _s »23» hydrochloric acid, obtained in a known manner, eg, by filtration, isolated and, where appropriate, by washing with an inert organic solvent. to be cleaned »

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For the preparation of metal salt complexes of azolyl-alkenones and oils of the formula (I), preference is given to salts of those anions and cations which have already been mentioned as preferred in connection with the description of the metal salt complex according to the invention.

The metal salt complexes of compounds of the formula (I) can be obtained in a simple manner by conventional methods, for example B, by dissolving the metal salt in alcohol, for example ethanol, and adding to the compound of the formula (I), Man can metal salt complexes in a known manner, s, 3 ». by filtration, isolation and, if necessary, by recrystallization clean «

The active compounds which can be used according to the invention intervene in the metabolism of the plants and can therefore be used as growth regulators,

For the mode of action of plant growth regulators according to the previous experience is that an active substance can also exert several different 'effects on plants »The effects of the substances depend in ^; substantially from the date of application in relation to the stage of development. of the plant and of the amounts of active substance applied to the plants or their surroundings and of the nature of the application. In any case, growth regulators are intended to influence crops in a specific manner

Plant growth-regulating substances can be used, for example, to inhibit the vegetative growth of plants. Such growth inhibition is of economic interest, inter alia with grasses, since this may increase the frequency

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the grass cuttings in ornamental gardens, parks and sports facilities, on roadsides at airports or in orchards are reduced, clay meaning also the inhibition of the growth of herbaceous and woody plants on roadsides and in the -! Sewage of pipelines or overland pipelines or gana generally in areas in which a strong growth of the plants is undesirable,

It is also important to use growth regulators to inhibit grain elongation. This reduces or completely eliminates the risk of plant encroachment before harvesting. In addition, growth regulators in crops can induce a straw boost, which also counteracts storage. The use of growth regulators for straw shortening and straw boosting allows higher fertilizer levels to be applied to increase yield without the risk of grain storage.

An inhibition of vegetative growth allows for a denser planting in many crops, so that more yields can be achieved in relation to the soil surface. The advantage of the smaller plants thus obtained is that the crop ¹ can be worked and fertilized more easily.

Sine inhibition of the vegetative growth of the plants may also result in an increase in yield in that the nutrients and assimilates benefit to a greater degree from flower and fruit formation than from the vegetative pollen.

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With growth regulators it is often possible to promote vegetative growth. "This is of great importance when the vegetative parts of plants are harvested. At the same time, the promotion of vegetative growth can lead to the promotion of generative growth by producing more assimilates so that more or more fruits are produced. "

Yield increases can be achieved in some cases by an intervention in the plant metabolism, without making changes in the vegetative growth noticeable. Furthermore, with growth regulators a change in the composition of the plants can be achieved, which in turn can lead to an improvement in the quality of the seed products For example, it is possible to increase the sugar content in sugar beet, sugarcane, pineapple and citrus fruit or to increase the protein content in soya or cereals. It is also possible, for example, to degrade desirable ingredients such as 3 ··· Sugar in sugar beet or cane, with growth regulators before or after the harvest to inhibit In addition, the production or the outflow of secondary plant ingredients can be positively influenced. An example is the stimulation of latex flow in gum trees.

Under the influence of growth regulators it can lead to the formation of parthenocarp fruits »Furthermore, the sex of the flowers can be influenced» Also, a sterility of the pollen can be produced, which in the breeding and production of hybrid seed has a great importance,

Through the use of growth regulators it is possible to control the branching of the plants

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Breaking the Apikaidominanz the development of side shoots are promoted, which may be very desirable especially in ornamental plants, in conjunction with a growth inhibition _o On the other hand, it is also possible to inhibit the growth of the side shoots * For this effect, z. Great interest in tobacco growing or planting tomatoes »

Under the influence of growth regulators, the foliage of the plants can be controlled to achieve defoliation of the plants at a timed time. Such defoliation plays an important role in the mechanical treatment of cotton, but is also of interest in other crops such as "B, in viticulture for the relief of crops." A defoliation of plants can also be made to transpire the plants to reduce before transplanting »

Likewise can be used with growth regulators!

ll

control-. On the one hand, a premature

O'·

"On the other hand, the clumps or even the fall of the flowers can be promoted to a desired extent- (" Thinning " ¹ ) ♦ To break the old dance." Alternans "means the peculiarity of some fruits, endogenously conditioned by year to year sehx different yields bring Su "Finally, it is possible to reduce with 'growth regulators at the time of harvest, the sum detach the fruit forces required to enable a mechanical Beemtung or manual Beerntung- · - ^su: facilitate"

T *] Q 4 "« ""

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or even delaying the ripeness of the harvested crop. "This is of particular advantage because it allows optimal adaptation to the needs of the market.

Furthermore, growth regulators can in some cases improve the fruit coloration, In addition, with growth regulators, a temporal concentration of maturity can be achieved · This creates the conditions for z, B, in tobacco, tomatoes and coffee complete mechanical or manual Beemtung in a Operation can be made »

In addition, the use of growth regulators can influence the seed or bud dormancy of the plants so that the plants, such as pineapples or ornamental plants in nurseries, germinate, sprout and flower at a time when they are normally unwilling to do so , Delaying budding or germination of seeds by growth regulators may be desirable in areas prone to frost to avoid damage from late frosts.

Finally, with growth regulators, a resistance of the plants to Prost, dryness or high salinity of the soil can be induced. This makes it possible to cultivate plants in areas which are normally unsuitable for this purpose.

The active compounds according to the invention also have a strong antimicrobicidal action and can be used practically for controlling unwanted microorganisms. The active compounds are suitable for use as crop protection agents.

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Crop protection agents are used to control Plasmodiophoromycetas, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Easidiomycetes, Deuteromycetes,. , ,

The good plant tolerance of the active ingredients in the concentrations necessary for the control of plant diseases allows treatment of aboveground plant parts, of plant and seed., And the soil,

As plant protection agents erfindimgsgemäßen active ingredients can be used with great success to combat such fungi, the real Mehltauerkrankungen.hervorrufen, so to combat Srysiphe species, such as z _o 3 »against the causative agent of cereal or cereal powdery mildew (Erysiphe graminis) for the control of barley barley disease (Drechslera grarainea), for the control of Venturis species, such as the antitussive pathogen (Venturis, inaequalis), or for the control of rice diseases, such as Pyricularia orysae and Pellicularia sasakii. _e

The active compounds can be converted into the customary formulations, such as solutions, emulsions. Suspensions, powders, foams, pastes, granules, aerosols, impurity encapsulations in polymeric substances and in coating compositions for seeds, as well as ULV formulations.

-O-

These formulations are prepared in a known manner, z, 3, by mixing the active ingredients with extender In ₅ so liquid solvents, liquefied gases under pressure and / or solid 'carriers, optionally with the use of surfactants, ie

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Emulsifiers, and / or dispersants and / or foam-forming agents, in the case of using water as an extender z * B. also organic. Solvents can be used as auxiliary solvents. The following are essentially embossed as liquid solvents: aromatics, such as. Xylene, toluene, or Alky! Naphthalenes, chlorinated aromatic or chlorinated aliphaticehe hydrocarbons such as chlorobenzenes ₃ Chlorethy.lene or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, s, 3, petroleum fractions, alcohols such as butanol or glycol and their ethers and esters , Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water. By liquefied gaseous diluents or carriers are meant liquids which are gaseous at normal temperature and under atmospheric pressure, for example "aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide." Solid carriers are embossed: s. B, ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as highly disperse silica, alumina and silicates, as solid carriers for granules kommen'in embossing: z _s B * crushed and fractionated natural 'rocks such as galcite, marble, pumice, sepioli.th, dolomite and synthetic granules of inorganic and organic flours and granules.'of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks, as emulsifying and / or whitening agents embossed: z, 3 "nonionic and anionic emulsifiers, such as polyoxyethylene-pettsäureester, polyoxyethylene fatty alcohol 'ether, eg. Examples of alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolysates. B * Li ₁ ^ InFormablau.ren.

h-rlcellulc. ^!

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In the formulations it is possible to use adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latice polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate,

Ss can be dyes such as inorganic pigments, z * 3 «iron oxide ,. Titanium oxide, ferrocyan blue and organic dyes such as alizarin ,. Azo and Metallphthalacyaninfarbstoffe and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, .Molybdän u ^ cL zinc, are used.

The formulations generally contain between 0.1 and 95 percent by weight of active ingredient, preferably between 0.5 and 90 Tb.

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

The active compounds can be used as such, in the form of their formulations or the prepared therefrom forms of application, such as ready solutions, emulsifiable concentrates, emulsions, foams, suspensions, wettable powders _t pastes, soluble powders, dusts and granules, "are used in the customary manner, z. 3 "by pouring, spraying, spraying, scattering, dusting, foaming, brushing, etc. It is also possible to apply the active ingredients according to the ultra-low-volume method or to inject the active ingredient preparation or the active ingredient itself into the soil * Bs can also be the seed of the plants-treated *

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When using the compounds according to the invention as plant growth regulators, the expenditure can be varied within a substantial range. In general, from 0.01 to 50 kg, preferably 0.05 to 10 kg, are used per hectare of soil.

When using the substances according to the invention as plant growth regulators applies that the application is made in a preferred period of time, the exact delimitation of which depends on the climatic and vegetative conditions.

Even when using the substances according to the invention as fungicides, the amount of effort can be varied within a substantial range, depending on the type of application. Thus, the active ingredient concentrations in the treatment of Pfianaenteilen in the application forms are generally between 1 and 0.0001 Gew .- 7b, preferably between 0.5 and 0.001 wt. -Fo * In seed treatment, in general, amounts of active ingredient from 0.001 to 50 g per kg of seed, preferably 0.01 to 10 g, required *. When treating the soil, 7% active concentrations of 0.00001 to 0.1% by weight, preferably 0.0001 to 0.02 %, are required at the site of action.

The preparation and the dewaxing of the substances according to the invention are illustrated by the following examples.

2446 14

Herstellunssbeispiele

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example 1

(CH.). C - CO - CH - CH = CH - / H

20 g (0.073 mol) of 6-cyclohe-3-yl-2,2-dimethyl-4- (1,2,4-triazol-1-yl) -4-hesen-3-one and 200 g of aluminum oxide are dissolved in 300 ml of methanol Heated under reflux for 24 hours. The reaction mixture is allowed to cool, filtered off with suction through kieselguhr and the IPiltrate is concentrated. This gives 19.9 g (99 % of theory) of 6-cyclohexyl-2, 2-dimethyl-4- (1, 2,4-triasol-1-yl) -

20 5-hexen-3-one of the refractive index η -q, = 1.4890.

Production of the original product

(CH _{3) 3} C

- CO

ι - CH ₀ -

44.4 g (0.2 mol) ¹ 2,2-dimethyl-t) -dinethylamino-4- (1,2,4-triasol-1-yl) -4-penten-3-one in 600 nl ether dissolved and at -20 ⁰ C with a solution of 48.2 g (0.24 KoI Cycloher-cylmethj'l-inagnesvanibroinid in 200 ml of ether., Ii is stirred for 1.5 hours, with the reaction mixture warmed to room temperature. JIit dilute Salssäure the Reakfionsgeciisch is adjusted ± n.er ± pH value of 7 to 8, on e. Thereafter, the organic phase is separated, washed aweimal with water, dried over Eatriumsnlfat and concentrated to give 27.4 g _(49}. 8 % of theory) 6-cyclohexane-2,2-dimethyl-4- (1,2,4-triasol-1-yl) -4-hes: en-3-one of

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20 refractive index n ^ = 1.4910,

b) (CH,) ₃ C - GO - C = CH - H (CH ₃ )

250.8 g (1.5 parts by weight) of 2,2-dimethyl-4- (1,2 _} 4-triazol-1-yl) -3-butanone are mixed with 196 g (1.65 mol) of dimethylformamide dimethyl acetal 5 The excess acetal is then distilled off to give 306 g (92 % of theory) of 2,2-dimethyl-5-dimethyl-amino-4- (1,2,4-triazol-1-yl) -4- penten-3 * -on of refractive index n ^ = 1.531 ·

c) (CH -) - C - CO - CH ₉ - Έ j

138 g (2 mol) of 1,2,3,4-2-riazole in portions at room temperature to give 276.4 g of '' - '(2 mol) ground potassium carbonate and 296.2 g (2 mol) of OC. Chlorine pinacolone in 500 ml of acetone, the internal temperature rises to boiling heat. The mixture is stirred under reflux for 5 hours and then cooled to room temperature. The reaction mixture is filtered and the filtrate is concentrated by distilling off the solvent in vacuo. The oily residue crystallizes after the addition of gasoline. This gives 240.8 g (72% of theory) of 2,2-Dimeth3'l-4- (1,2,4-triasol-1-yl) -3-butanone of melting point 62 to 64 ⁰ C.

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Example 2

OH (CH ₃ ) ₃ C - CH - CH - CH = CH

A Jl

.1.0.4 g (0.038 mol) of 6-cyclohexyl-2,2-dimethyl-4- (1, 2,4-triazol-1-yl) -5-he: H: en-3-one (Example 1) are dissolved in 100 ml of methanol and treated at -10 ⁰ C dropwise with a solution of 0.38 g (0, -01 mol) of sodium borohydride in 5 ml of ice water. The mixture is stirred for 2 hours and then the reaction mixture with dilute hydrochloric acid to a ^; pH of β to 7. The reaction mixture is concentrated by distilling off the solvent in vacuo. The residue is taken up in methylene chloride, washed with water, dried over sodium sulfate and concentrated. 8.9 g (86 % of theory) of 6-cyclohexyl-2,2-dimethyl-4- (1,2,4-triazole) are obtained.

20 1-yl) -5-hexen-3-ol of refractive index η-η = 1.4920.

The following compounds of the formula (I) are obtained in a corresponding manner and according to the processes indicated:

Table 2

R ¹ - Σ - CH - GH = CH - R ² (I)

1 4

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Ex,

X Ί ο.

Melting point (C) refractive index ni

'(GHO-, C-

J J

(GH ₃ J ₃ G-

(CH ₃ J ₃ C-

(CH ₃ J ₃ C- (CH ₂ ) -, Ο ΙΟ (CH ₃ J ₃ C -. (CH-, J ^ C-

CcH-) - σ-

(CH - ^) - C-

(Gl CH ₉ G '(CH ₃ ) | -

CO IT

CO IT

CO IT

CO IT

CO -IT

CO Ή

CO 1

CO If

CO Ή

CO IT

CO., E

CO Έ

GO I

3-GH (OH) IT (CH ₀ J ₃ G-GH (OH) H

(CHOnC-'CH (OH)] J (CH ₃ ) ₃ C- .GH (OH) I

(CHO ₃ C-CH (OH) U

3-GH (OH) H

-C ₃ H ₇ -I

gl

F 1

Cl

(CH ₃ J ₃ C-CH (OHJxT

(TTT / T TJ _ ·

"VIiA ^-1 W '-i-dry" ** J-

^ - 3 1

-G ₃ n ₇ -i Cl

-C ₃ H ₇

►01

P TT _?

- (JH ₂ -G ₃ I

1.5388 1.4778 1.4880 105-08 1.5512 1.4871 1.4868 1.5434 138-40 1.5624

1,4885 1,4969

1.4777

tough oil

1.4898

1.4798

1.5633

1.4841

1.4857

1.4807

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Ex,

Λ.

R ²

Melting point ( ⁰ C). Refractive index n |?

23 (CH ₃ J ₃ C-

24 (CH ₃ ) .C-

25 (CH) 0-

27 (CH ₃ ) ₃ C-23 (CH -). C-

30 PCH ₉ C (CH.) .- 31

32 (CH ₃ J ₃ C-

33 (CH ₃ J ₃ C-

37 (m

CH -,) C.

^{J "Uii} 3 ^ 3 ^and 40 (CH,). C-

/ 1 1 ι '--1) [ -

42 (CH.). C-

; CH (OH) ΙΪ

CH (OH) Ή CH (OH) Έ CH (OH) II CH (OH) IT

CH (OH) IT

CH (OH) 1 CH (OE) U CH (OH) Ή CO CH

CO CO CO CO

coco co

co

CH (OH) GH (OH) -

CH (CJI, -)

-CH (C ₂ H.)

η TJ <- 3

112-24

154-56 (A-IOrm.)

46-48 (B shape)

180 (A-shape).

1.4832

1.4832

CH,

^J 3i

~ ^C 6 ^H 13

j.p-o.xir -, - x!, q-O -? ^

50-60, 1.4915.

1,4773 1 .., 4808 1.4742 · L ₅ 4770 1.4390 Sauge OeI 1.5018

η tr

m 0 1 ι

Cl "5 ⁿ 11

vl

-C-H ..

O 13

, 4392

92-96 1.4742

4 6 14 2 -

(CH ₃ ) ₃ G- CH (OH) GH 03/16/1983 GO Έ AP A 0 _% M / 244 614 CO ή 61 425 12 Ex. He. C ₃ H ₇ -C (CI I ₃ ) ₂ -CH (OH) Έ R ² saturation point ( ⁰ G) ₂₀ breaking point: n _ß 43 - ^) 1.5050 44 45 0 107-11 (XCuCl ₂ ) 46 CHp-C ₃ H ₇ -I 1.4849

A- and 3-Irorm = the two possible geometric isomers

47 CH _n O-

48 (OH ₃ ) ₃ C-

49 (CH ₃ ) ₃ C-

50 .. (CH-), C-

51 (CH ₃ ) ₃ C-

52 Cl

53 CH ₃ O-

54 Cl

55 C ₃ H ₇ -CC CH ₃ ) ₂ -

56 (CH ₃ J ₃ C-

57 (CH -) - C-

CH (OH) Έ CO Έ CO Έ CE (OH) Έ CH (OH) Il CH (OH) Ή CH (OH) IT CH (OH) Έ CO -. Ή CO Έ

C ₂ Ii ₅ 1.5320 (A-Porm)

-CH ₂ -C (CHA 1.4823

-CH ₂ -C (CH ₃ ^ 6 2 -CH ₂ -C ₃ H ₇ -i49 C ₉ H.

2 * 5

CH (OH)

40 (B-Fcrm) 67 ί 1, -4819

: ^J 1,4772

, -GH (CHo) 1.4819

- Ηγ-,

1.5996

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Yerwend un gsbei games

In the following examples, the following compounds are used as the equivalent of the same:

^ .US.

(A) = (CH ₃ ) ₃ G-CH-CH-CH = C

ir <

'3

CH

(CHO ₀ C-CH-CH-CH = 3 3 j

OH

CH.

CH-CH = C

GH

CH.

(D) = (CH ₀ ),

OH!

nrr / ITJ -Ti- / \

(Ξ) = (CH ^) ο C-GO-CH-GH =

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Example A Inhibiting soybeans

Solvent: 30 parts by weight of dimethylformamide Emulsifier: 1 part by weight of polyosy- lene-sorbitan monoaurate

To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the mixture is added to the desired concentration with water.

Soyabohrienpflansen-be in the greenhouse until fully unfolded the first IPolgeblattes. At this stage, the plants are sprayed dripping wet with the WirkstoffZubereitungen, laughing after 3 weeks, the growth is measured in all plants and calculated the growth inhibition in percent of the growth of the control plants. It means 100 % inhibition of growth and 0 % growth, according to the control plants »

The active compounds 21 and 19 according to the invention show better growth inhibition in this test than the compound (A) known from the prior art. ,

Example B

Wuchshemmun ^; in the case of grass (Pestuca p ratensis)

Solvent: 30 parts by weight of dimethylformamide Emulsifier: 1 part by weight of polyosylethylei-oorbitan mono-

laurat

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To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the specified amounts of solvent and emulsifier and filled with water to the desired concentration.

Grass (Festuca pratensis) is sucked in the greenhouse up to a stature height of 5 cm. At this stage, the plants are sprayed dripping wet with the drug formulations. After 3 weeks, the growth is measured and the growth inhibition in percent of the growth of the control plants is calculated. Ss 100 % inhibition of growth means the stoppage of growth and 0% growth corresponding to that of the control plants *

The active compound 21 according to the invention exhibits a substantially better growth inhibition than the compounds (A) and (B) known from the prior art.

Example C - Growth in sugar beet

Solvent: 30 parts by weight of dimethylformamide Smulgator: 1 part by weight of polyoxyethylene sorbitan

Monolaurate ·

To prepare a suitable Wirkstoffzubereitung- mixed, 1 part by weight of active compound with the stated amounts of solvent and emulsifier Lind filled with water to the desired concentration »

Sugar beets are grown in the greenhouse until the cotyledons have fully developed. At this stage, the plants are sprayed dripping wet with the preparation of active compound.

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I ¹ TaGία 14 days, the growth of the plants is measured and the growth influence as a percentage of the growth of the control plants is calculated. It means 0 % 7 / uch influencing a growth corresponding to that of the control plants, negative values characterize a growth hike, positive growth promotion compared to the control plants.

The active compounds 16, 18, 19, 21, 26, 36 and 41 according to the invention in this test show a greater growth-influencing effect than the compounds (G) and (L) known from the prior art.

Example D

Growth inhibition in cotton

Solvent: 30 parts by weight of dimethyl · ormaraid emulsifier: 1 part by weight of polyosyethylene-sorbitan mono-

laurat

To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the specified amounts of solvent and emulsifier and the mixture is filled with water to the desired concentration,

Cotton plants are grown in the greenhouse until the 5-leaf leaf is fully unfolded. At this stage, the plants are sprayed to drip point with the active ingredient preparations. After 3 weeks, the growth of the plants is measured and the growth inhibition in percent of the increase of the control is calculated. 100 % inhibition of growth means the stoppage of growth and 0 % growth corresponding to that of the control plants.

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The erfiiidiiagsgernäioen active substances 1,6,10,11,16 and 25 show in this iest a better growth inhibition than the known from the prior art compounds (A), (B) and (E),

Example Ξ.

Stimulation of CO ₀ -isolation in soybeans

Solvent: 30 parts by weight of dimethylformamide

Emulsifier: 1 part by weight of polyosyethylene-sorbitan mono-

laurat

To prepare a suitable Wiriestoffzubereitung mixed 1 part by weight of active compound with the stated amounts of solvent and emulsifier and filled with water to the desired concentration.

So.john bean plants are grown in the greenhouse until the full deployment of the first follower sheet. At this stage, the plants are sprayed dripping wet with the WirkstoffZubereitungen. In the further course of the experiment, the CQ, -, - Fisierung the plants is measured by conventional methods. The values are compared with those not with 'control plants treated with active ingredients.

oecieuten:

- Inhibition of CO _? Fixation 0 COρ fixation as in control. + Low stimulation of CQp-Fisi -ι- + strong stimulation of CQp-iPixation +++ very strong stimulation of C0 _o fixation.

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The active compounds 1 and 22 according to the invention show, in this test, a stimulation of CO 2 ffization in contrast to the compounds (A), (B) and (E) known from the prior art.

Example ff Erysiphe test (barley) / protective

Solvent: 100 parts by weight of dimethylformamide. Emulsifier: 0.25 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier and the condensate is diluted with water to the desired concentration.

To test for protective activity, spray young plants with the active ingredient preparation dew-well. Stach drying of the spray coating, the plants with spores of Erysiphe graminis f. sp. hordei pollinated.

The plants are placed in a greenhouse at a temperature of about 20 ⁰ G and a relative humidity of about 80 % , in order to promote the development of Mehltauustusteln ',

7 days after the inoculation the evaluation takes place.

A marked superiority in: the activity over the known from the prior art compound (S) show in this test z. 3. the compounds according to the following

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Production Examples: 5, 32, 34, 35, 36, 40, 42, 38, 6, 17, 18, 19, 20, 21, 22, 10, 11, 25 and 12.

Example G

Drechslera graminea test (barley) / seed treatment (syn. Helminthosporium gramineum)

The use of the active ingredients is carried out as a dry dressing, they are prepared by stripping the respective active ingredient with rock flour to a finely powdered mixture, which ensures a uniform distribution on the seed surface. ,

For dressing, shake the infected seed for 3 "minutes with the mordant in a sealed glass bottle.

The seed in sealed Fetrischaien in the refrigerator 10 days-long sets, embedded in sieved, moist standard soil and a temperature of 4 ^'0 G from. The germination of the barley and possibly also the fungal spores is initiated. Then sow the pregerminated barley with 2 χ 50 grain 3 cm deep into a standard soil and cultivate it in the greenhouse at a temperature of ca 18 C in seed boxes, which are exposed to light for 15 hours daily.

Approximately 3 weeks after sowing, the plants are evaluated for the symptoms of streak disease.

Sine clear superiority in the effectiveness compared to the known from the prior art compound (3) show in this test z. 3. the compounds according to the following preparation examples: 17 and 21.

Claims (5)

14 16.3.1333 AP A 0 Ή / 244 61 524 12 Claim for invention 1 2 Z and Z are the same or different and are hydrogen, halogen, or alkyl of 1 to 4 carbon atoms, and further R is phenyl which may be mono- or polysubstituted by identical or different substituents, by halogen, alkyl having 1 to 4 carbon atoms, alkoxy and ,. Alkylthio each having 1 to 4 carbon atoms, alkyl and dialkylamino each having 1 to 4 carbon atoms in each alkyl moiety, further halogenoalkyl, haloalkoxy and haloalkylthio each having 1 to 2 carbon atoms and 1 to 5 identical or different halogen atoms, phenyl and / or phenoxy, wherein the two last-mentioned radicals in turn may be substituted by halogen and / or Alley 1 having 1 to 2 carbon atoms R ~ for straight-chain or branched alkyl having 1 to 12. Carbon atoms, furthermore, is phenyl, which - - "may be monosubstituted, polysubstituted or differently substituted by halogen, alkyl having 1 to 4 carbon atoms, alkoxy and alkylthio each having 1 to 4 carbon atoms, alkyl and dialkylamino each having 1 to 4 Carbon atoms in each alkyl moiety, also haloalkyl, - Ha log ens. Ik oxy and haloalkylthio each having 1 to 2 carbon atoms and 1 to 5 identical or different halogen atoms. Phenyl and / or phenoxy, -wobei the latter two radicals in turn may be substituted by halogen and / or alkyl having 1 to 2 carbon atoms, or R is optionally substituted by halogen and / or alkyl having 1 to 4 carbon atoms substituted cycloalkyl with 2U6U 2 - 03/16/1983 AP A O K / 244 614 61 524 12 1 "Plant growth regulating and fungicidal agents, characterized by a content of at least one azolyl alkenone or oil of the formula (I) R ¹ - - Σ - CH - CH = CH - R ² (I), in which R is alkyl, haloalkyl or optionally substituted phenyl, R ^{w is} alkyl, optionally substituted phenyl, optionally substituted cycloalkyl or optionally substituted cycloalkylalkyl, X stands for the CO or CH (OH) group. And Y 'is a nitrogen atom or the CH group, and their acid addition salts and metal salt complexes, in addition to extenders, and / or surface-active substances, 2. Composition according to item 1, characterized in that they contain azolyl-alkenones and oils of the formula (I) - in which CEpS R for the grouping -C-CHo 446 14 2 - 03/16/1983 AP A O U / 244 614 61 524 12 3. A method for regulating plant growth and controlling fungi, characterized in that azolyl-alkenones or oils of the formula (I) or their acid addition salts or metal salt complexes are applied to the plants and / or their habitat or affect the fungi or their habitat. 3 to 7 carbon atoms or optionally substituted by halogen and / or alkyl having 1 to 4 carbon atoms substituted cycloalkylalkyl. 3 to 7 carbon atoms in the cycloalkyl part and 1 to 2 carbon atoms in the alkyl part, X represents the CO or GH (OH) group and Y represents a nitrogen atom or the CH group. - 4. Use of azolyl-alkenones and oils of Forme1 (I) or, respectively, of acid addition salts or metal salt complexes of azolyl-alkenones and oils of the formula (I), characterized in that they are used to regulate plant growth or used to combat fungi. 5 »Process for the preparation of plant growth regulators or» fungicidal agents, labeled. characterized by mixing azolyl-alkenones or oils of the formula (I) or »acid addition salts or metal salt complexes of azolyl-alkenones or -ols of the formula (1) with extenders and / or surface-active substances,