CA1185608A - Azolyl-alkenones and -ols, a process for their preparation, and their use as plant-growth regulators and fungicides - Google Patents

Abstract

ABSTRACT OF THE DISCLOSURE

Azolyl-alkenones and -ols of the general formula in which R1 represents all alkyl radical, a halogenoalkyl radical or a phenyl radical, which phenyl radical is optionally monosub-stituted or polysubstituted by identical or different substituent(s) selected from halogen, alkyl having 1 to 4 carbon atoms, alkoxy and alkylthio, each having 1 to 4 carbon atoms, alkylamino and dialkylamino, each having 1 to 4 carbon atoms in each alkyl part, and also halogenoalkyl, halogenoalkoxy and halogenoalkylthio, each having 1 or 2 carbon atoms and 1 to 5 identical or different halo-gen atoms, phenyl and phenoxy, it being possible for the two last-mentioned radicals in turn to be substituted by halogen and/or alkyl having 1 or 2 carbon atoms; R2 represents an alkyl radical, a phenyl radical, which phenyl radical is optionally monosubsti-tuted or polysubstituted by identical or different substituents selected from halogen, alkyl having 1 to 4 carbon atoms, alkoxy and alkylthio, each having 1 to 4 carbon atoms, alkylamino and dialkylamino, each having 1 to 4 carbon atoms in each alkyl part, and also halogenoalkyl, halogenoalkoxy and halogenoalkylthio, each having 1 or 2 carbon atoms and 1 to 5 identical or different halo-gen atoms, phenyl and phenoxy, it being possible for the two last-mentioned radicals in turn to be substituted by halogen and/or alkyl having 1 or 2 carbon atoms, a cycloalkyl radical which cyclo-alkyl radical is optionally substituted by halogen and/or alkyl having 1 to 4 carbon atoms or a cycloalkylalkyl radical which cyclo-alkylalkyl radical is optionally substituted by halogen and/or alkyl having 1 to 4 carbon atoms; X represents a CO or CH(OH) group;
and Y represents a nitrogen atom or a CH group; and their acid addi-tion salts and metal salt complexes are new, are prepared as des-cribed and find use as plant-growth regulators and fungicides.

Description

Le A 21 385-C~

The present invention re]a-tes to cer-tain new azolyl-alkenones and -ols, to a process for -their produc-tion, and to -their use as plant-growth reguiatc)rs and fungicides.
It has already been disclosed tha-t cer-tain 6,6-disub-stituted 2,2-dimethyl-4-(1,2,4--triazol-1-yl)-hex-5-en-3-ones and -ols possess good plant growth-regulating and fungicidal properties (see DE-OS (German Published Specification) 2,905,981). However, the action of these compounds is no-t always comp:l.etely satisfac-tory, in particular when low amounts and concentrations are used.
The present invent.ion now provides, as new compounds, the azolyl-alkenones and -ols of -the general formula R - X - CH - CH = CH - R
~ N~

N l I
in which Rl represents an alkyl radical, a halogenoalkyl radical or a phenyl radical, which phenyl radical is op-tionally monosub-stituted or polysubstituted by identical or different substituent(s) selected from halogen, alkyl having 1 to 4 carbon a-toms, alkoxy and alkylthio, each having 1 to 4 carbon atoms, alkylamino and dialkylamino, each having 1 -to 4 carbon a-toms in each alkyl part, and also halogenoalkyl, halogenoal]coxy and halogenoalkyl-thio, each having 1 or 2 carbon atoms and 1 -to 5 identical or different halo-gen atoms, phenyl and phenoxy, it being possible for -the -two las-t-mentioned radicals in turn to be substituted by halogen and/or alkyl having 1 or 2 carbon atoms; R2 represents an alkyl radical, a phenyl radical, which phenyl radical is optionally monosubsti-tuted or polysubstituted by iden-tical or different substi-tuen-ts selected from halogen, alkyl having 1 to 4 carbon atomsl alkoxy 23189-5447 ~ b and alkylthio, each having 1 to 4 carbon atoms, alkylamlno and dialkylamino, each having 1 to 4 carbon a-toms in each alkyl part, and also halogenoalkyl, halogenoalkoxy and halogenoalkylthio, each having 1 or 2 carbon atoms and 1 to 5 identical or difEerent halo-gen atoms, phenyl and phenoxy, it being possible -for the two last-mentioned radicals in turn to be substituted by halogen and/or alkyl having 1 or 2 carbon atoms, a cycloalkyl radical, which cycloalkyl radical is optionally substituted by halogen and/or alkyl having 1 to 4 carbon atoms or a cycloalkylalkyl radical, which cycloalkylalkyl radical is optionally substitu-ted by halogen and/or alkyl having 1 to 4 carbon atoms; X represents a CO or CH(OH) group; and Y represen-ts a nitrogen atom or a CH group; and the acid addition salts and metal salt complexes thereof.
The compounds according to the invention, of the formula I, occur as the geometric isomers E(trans) and Z.(cis). In the E,Z nomenclature, the substituents located at the double bond are : placed in order of decreasing priority, according to the Cahn-Ingold Prelog rule. If the preferred substituents are located on the same side of the doubl.e bond, the configuration Z (derived from "zusammen" (together)) is present, and if they are located ~ - la -on opposite sides, the configuration E (derived From "entgegen" (opposed)~ is present.
In addition, when X=CH(OH), the compounds according to the invention, of the formula (I), possess two asymmetric carbon atoms; they can then be present as the two geometric isomers (threo form and erythro form), which may be obtained in varying proportions. In both cases, -they are present as optical isomers.
The invention also provides a process for the production of a compound of the present inven-tion, characterised in that a compound of the general formula R1 _ CO - f = CH - CH2 - R2 (II) ~N~y N
in which R1, R2 and Y have the meanings given above, is heated in the presence of a diluent and, if appropriate, in the presence of a catalyst or in the presence of alu-minium oxide, and, if a compound in which X represents a CH(OH) group is required, the resulting azolyl-alkenones according to the invention, of the general formula R1 _ CO - CH- CH = CH - R2 ¦ (Ia) N~y I!

: in which R1, R2 and Y have the meaning given above, is reduced;
and, if desired, an acid or a metal salt is added onto the compound of the present invention produced by the foregoing process.
Finally, it has been found that the new azolyl-Le A 21 385 ~, _ , ~ r~

alkenones and -ols of the formula (I), and their acid addition salts and metal salt complexes, possess powerful plant growth-regulating properties and powerful fungicida:L
properties.
In addition, the new azolyl-alkenones and -ols of the formula (I) are interesting intermediate products ~or the preparation of further plant protection ager1ts.
In the keto derivatives, the keto group can be reduced not only to a -CH(OH~ group (according to the invention) but also to a -CR(OH) group. 8y appropriate reactions, it is also possible to obtain functional derivatives of the keto group, such as oximes and oxirne ethers, hydrazones and ketals. The hydroxyl group of the carbinol derivatives can be converted into -the corresponding ethers in a cus-tomary manner. Furthermore, acyl derivatives of carbamoylderivatives of the compounds of the formula (I) can be obtained by reaction with, for example, acyl halides or carbamoyl chlorides, in a manner which is known in principle.
Surprisingly, the compounds according to the 2n invention poe,sess a better plant growth-regulating and fungicidal action than the 6,6-disubstituted 2,2-dimethyl-4-(1,2,~-triazol-1-yl)-hex-5-en-3-ones and -ols which are known from the prior art and are similar compounds chemic-~; ~ ally and with regard to their action. The active com-pounds according to the invention thus represent an enrich-ment of the art.
Preferred compounds according to the present invention are those in which R1 represents a grouping of the general formula ~CH2Z

wherein Le A ~1 38 z1 and z2 are identical or different and rPpresen-t a hydrogen or halogen atom or an alkyl radical having l to 4 carbon atoms; ~
R1 represents a phenyl radical which is optionally monosubstituted or polysubstituted (the substlt-uent(s) thereon preferably being selected from halogen, alkyl having l to 4 carbon atoms, alkoxy and alkylthio, each having l to 4 carbon atoms, alkylamino and dialkylamino, each having 1 to ~
carbon atoms in each alkyl part, and also halo-genoalkyl, halogenoalkoxy and halogenoalkylthio, each having l or 2 carbon atoms and l to 5 iden-tical or dlFferent halogen atoms, such as fluorine atoms and chlorine atoms, and phenoxy and phenyl : 1S optionally substituted by halogen and/or alkyl having l or 2 carbon atoms);
. ~ R2 represents a straight-chain or branched alkyl radical having l to 12 carbon atoms; phenyl which is optionally monosubstituted or polysubstitited

2~ by identical or different substituents (the substituent(s) thereon preferably being selected from halogen, alkyl having l to 4 carbon atoms, : alkoxy and alkylthio, each having l to 4 carbon atoms, alkylamino and dialkylamino, each having l to 4 carbon atoms in each alkyl part, and also halogenoalkyl, halogenoalkoxy and halogenoalkylthio, each having l or 2 carbon atoms and l to 5 identical or different halogen atoms, such as fluorine atoms ; ~ and chlorine atoms, and phenoxy and phenyl option-` 30 ally substituted by halogen and/or alkyl having l or 2 carbon atoms);
and furthermore : R2 preferably represents a cycloalkyl or cyclo-alkylalkyl radical which is optionally monos~lb-stituted or polysubstituted by identical or different ~: :
Le A 21 ~85 :

substituents and each of which has 3 to 7 carbon atoms in the cycloalkyl part and l or 2 carbon atoms in each alkyl part (the following being mentionPd as preferred substituents: alkyl having l to 4 carbon atoms and halogen)S
X represents a CO or CH(OH) ~roup and Y represents a nitrogen atom or a CH group.
Particularly preferred compounds of the present : invention are those in which R1 represents a grouping of the general formula ~CH2Z
-C-CH3 , wherein z1 and z2 are identical or different and repre-~: l5 sent a hydrogen, fluorine, chlorine or bromine atom or a methyl, ethyl, propyl or butyl; or Rl represen-ts a phenyl radical which is optionally ; monosubstituted to trisubstituted by iden-tical or .~ different substituents selected from fluorine7 chlorine, methyl, isopropyl, tert.-butyl, methoxy, methylthio, isopropoxy, trifluoromethyl, tri-~` fluoromethoxy, trifluoromethylthio, methylamino, dimethylamino, and phenoxy or phenyl optionally substituted by fluorine, chlorine or methyl;
R2 represents a straight-chain or branched alkyl : radical having 1 to 8 carbon atoms, or a phenyl which is optionally monosubstituted to trisub-stituted by identical or different substituents selected from fluorine, chlorine, methyl, isopropyl, tert.-butyl, methoxy, methylthio, isopropoxy, trifluoromethyl, trifluoromethoxy, trifluoromethyl-thio, methylamino, dimethylamino, and phenoxy or Le A Z1 }E: 5 v~

phenyl optlonally substituted by fluorine, chlorine or methyl; and R2 furthermore represents a cyclopropyl, cyclo-butyl J cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylme-thyl, cyclopentylmethyl or cyclo-hexylmethyl radical, each of which is optionally substituted by methyl~ ethyl 9 isopropyl, fluorine or chlorine;
X represents a CO or CH(OH) group and Y represents a nitrogen atom or the CH group.
In addition to the co~pounds mentioned in the preparative Examples, the following compounds of the gen-eral formula (I) may be men-tioned individually (wherein X represents the CO or the CH(OH) group and Y represents ~ 15 a nitrogen atom or the CH group):
I Table l R1 - X - CH - CH = CH - R2 ~N~y (I) N !l . ~
::~ R1 R2 H3C- C- -CH2-CH(CH3)2 ~:
:` CH2Cl : H3C-C- -CH2-CH(C~I3)2 C~12Cl (CH3)3C- -CH

(CH3)3C- -CH~
:~
~ ~ Le A ~1 385 Table 1 (~on-tinuation) ~1 R . . -(CH3)3C- -CH

(CH3)3c- -CH2 ~
(C~3)3c- -CH2-cH(cH3)c2Hs (CH3)3C- -CH2-CH(CH3)C3H7 (CH3)3c- -CH2-CH(CH3)C4Hs (CH3)3c_ -CH2-C(CH3)3 (CH3)3C- -CH2-CH(C2Hs)2 (CH3)3C_ -CH2-CH(C3H7)2 (CH3)3C- -CH

(CH3)3C- -CH

(CH3)3c- -CH2 ~

( CH3 ) 3C- -CH2\~3 ~ (CH3)3c_ -CH(CH3)-CH(CH3)~
: : (CH3)3C- -C(CH3)2-CH(CH3)2 ; (CH3)3c_ ~ OCF3 (CH3)3C- - ~ OSCF3 (CH3)3C- ~ OCH3 (CH3)3C- ~ Cl Le A 21.:.385 Tabl.c l (continuation) .~
Rl R2 , . . .
~,., . " .

(CH3)3C- ~ Cl Cl H3C~_~
(CH3)3C- H3 ~ CH3 (CH3)3C_ ~ C(CH3)3 (CH3)3C- ~ CF3 (cH3)3c- ~

(CH3)3C- ~ N(CH3)2 (CH3)3c_ Cl SCH3 (CH3)3C_ (C~13)3C- - ~ Cl ~CH3 (CH3)3c_ Cl CH3 Preferred compounds according to the invention, of course, also include addition products of acids on those azolyl-alkenones and -ols of the formula (I) in which R1, R , X and Y have the respective meanings which have already been menkioned in respect of preferred and particularly preferred compound of the invention.

Le.A 21 385 -The acids which can be used to form adducts include, as preference, hydrohalic acids (such as hydrobromic ac.id and9 especially, hydrochloric acid), phosphoric acid, nitric acid, sulphuric acid, monofunctional and bifunctional carboxylic acids and hydroxycarboxylic acids (such as acetic acid 9 maleic acid, succinic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid and lactic acid) and sulphonic acids (such as p-toluenesulphonic acid and naphthalene-1,5-disulphonic 1~ acid)~
Prcferred compounds according to the inv~ntion also include addition products of salts of metals of main groups II to IV and of subgroups I and II as well as IV to VIII, with those azolyl-alkenones and ols of the formula (I) in which Rl, R2, X and Y ha~e the respective meanings which have already been mentioned in the description of preferred and particularly preferred compounds of the invention.
Arnongst these salts, salts of copper, zinc, manganese, ma~nesium, tin, iron and nickel are particularly preferred Suitable anions of these salts are those which are derived from those acids which produce physiologic-ally tolerated addition products. Particularly pre-ferred acids of this type, in this connection, are hydro-halic acids (such as hydrochlic acid and hydrobromic acid), and also phosphoric acid, nitri.c acid and sulphuric acid.
If, for example, 6-cyclohexyl-2,2-dimethyl-4-(1,2,4-triazol-1-yl)-hex-4-en-3-one is used as the starting material, aluminium oxide is used as a reactant and methanol i8 used as the diluent, the course of the reaction according to the process of the invention can be represented by the following equation:

Le A 21 ~85 Al2o3/cH3oH
(CH3)3C-CO-C-cH-cH2 ~ ~~ ~~~ >
Nl N (CH3)3C-CO-CH-CH=CH

~ N

If, for example, 6-cyclohexyl-2,2-dimethyl-4-(1~2,4-triazol-1-yl)-hex-5-en-3-one is used as -the starting material and sodium borohydride is used as the reducing agent, the course of the reaction according to the process - of the invention can be represented by the following equation:

NaBH4 (CH3)3C-CO-CH-CH=CH ~ -- - 73 `N (CH3)3C-C~ CH-CH=CH

N ~

~; ~
Preferred compounds of formula (II) required as starting materials in carrying out the process according to : the invention are those in which R1, R2 and Y have those :~: meanings which have already been mentioned for these sub-: : stituents in connection with the description of the ~; preferred and particularly preferred compounds according to the invention.
The compounds of the formula (II) are known or can be prepared in a simple manner, according to pro-cesses which are known in principle (see DE-OS (German : Published Specification) 3,000~643 and the literature q~oted therein). Thus a campound of the formula (II) is ottained by reacting a keto-enamine of the general formula :~ Le A.21 385 .

.

~ ~5~

R1 _ CO - C = CH - N (III) 'N`y \ R4 N ¦¦
in which R and Y have the meaning given above and R3 and R4 are identical or different and represent an alkyl radical having l to 4 carbon atoms, especially a methyl radical, with an organo-magnesium compound of the general formula Hal - Mg - R2 (IV) in which : 10 R2 has the meaning given above and Hal represents a halogen atom, in the presence of an iner-t organic solvent (such as ether), and, if appropriate, in the presence of an inert gas (such as nitrogen), at a temperature between -20 and 120C (in this context, see also DE-05 (German Published Specification~ 3,000,643 and th~ preparative Examples).
~ The keto-enamines of the formula (III) are known : ~ or can be prepared in a simple manner, according to pro~
cesses which are known in principle (see DE-OS (German Published Specification) 3,000,643). Thus, a keto-amine of the formula (III) is obtained by reacting, at the boil, an azolyl-ketone oF the general formula R1 - C0 - CH2 - N ~ N (V) in which ~ ~5R1 and Y have the meaning given above, : with an amide acetal or aminal ester of the general Formula Le A 21, 385 CH-N (VIa) R50 \ R4 or R50-C~ / (VIb) \ NR3R4 in which R3 and R4 have the meaning given above, and R5 represents an alkyl radical having 1 to 4 carbon atoms, in a manner which is in itself known, in the presence of an inert organic solvent, such as an aromatic hydrocarbon and such as, especially, an amide acetal or aminal ester, of the formula (VIa) or (VIb), employed in excess (in this 10 context, see also Chem. 8er. 101, 41-50 (1968); J. Org.
Chem. 43, 4,248-50 (1978), and the preparative Examples).
The azolyl-ketones of the formula (V) are known (see, for example, I)E-OS (German Published Specification) 25431,407 and DE-OS (German Published Specification) 15 2,610,022 and DE-OS (German Published Specification) 2,638,470); or they can be prepared according to customary methods, by reacting the corresponding halogeno-ketones with 1,2,4-triazole or imidazole, in the presence of an acid-binding agent.
The amide acetals or aminal esters of the formulae (VIa) or (VIb) are generally known compounds of organic ~hemistry (see, for example, Chem. Ber. 101, 41-50 (1968) ` and J. Org. Chem. 43, 4,248-50 (1978)).
; The organo~magnesium compounds of the formula (IV) 25 are generally known compounds of organic chemistry.
Suitable diluents for the process, according to the invention, for the preparation of the azolyl-alkenones of the formula (Ia) are organic solvents which are inert Le A 21 385 '' `-' .

. .

"

under the reaction conditions. These include, as preferences, 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) J and halogenated hydrocarbons (such as methylene chloride, carbon tetrachloride, chloroform or chlorooenzene).
The process, according to th~ invention, for the i preparation of the azolyl-alkenones of the formula (Ia) is carried out, if appropriate, in the presence of a base ; as a catalyst. ThesP include, as preferences, organic nitrogen bases, such as morpholine, pyridine, triethylamine and N,N-dimethylbenzylamine.
In the process, according to the invention, for the preparation of the azolyl-alkenones of the formula (~a) the reaction temperatures can be varied within a rela-tively wide range. In general, the reaction is carried out at a temperature bétween 30 and 150C, preferably between 50 and 120C.
The process, according to the invention, for the preparation of the azolyl-alkenones of the formula (Ia) is carried o~t either completely thermally, by heating the compounds of the formula (II), or as a base-catalysed reaction, O.l to l mol of base being employed per mol of ; 25 the compounds of the formula (II), or in the presence of aluminium oxide. The compounds according to the inven-tion are isolated in a customary manner in all cases.
~ The reduction, according to the invention, for ; the preparation of the azolyl-alkenols of the formula (I) is effected in a customary manner, for example by reacting the azolyl-alkenone of the formula (Ia) with a complex hydride, if appropriate in the presence of a diluent, or by reacting the azolyl-alkenone of the formula (Ia) with aluminium isopropylate in the presence of a diluent.
3S If complex hydrides are used, suitable diluents Le A 21 ~as for this reaction according to the invenkion are polar organic solvents. These include, as preferences, alcohols (such as methanol, ethanol,butanol or isopropanol) and ethers (such as diethyl ether or tetrahydrofuran). The reaction is carried out in general at a temperature from 0 to 3ûC, preferably at from 0 to 20C. For this purpose, about l reaction equivalent of a complex hydride (such as sodium borohydride or lithium alanate) is employed per mol of the ketone of the formula (Ia). To isolate 10 the reduced compounds cf thP formula (I), the residue is taken up in dilute hydrochloric acid, and the solution is then rendered alkaline and extracted with an organic solvent.
The further working-up is effected in a customary manner.
If aluminium isopropylate is used, preferred 15 diluents for this reaction a~cording to the invention are alcohols (such as isopropanol), or inert hydrocarbons (such as benzene). The reaction temperatwres can again be varied within a relatively wide range; in general, the reaction is carried out at a temperature between 20 and 20 120C, preferably at from 50 to 100C. To carry out ~; the reaction, about l to 2 mnl of aluminium isopropylate are employed per mol of the ketone of the formula (Ia).
To isolate the reduced compounds of the formula (I)~ the excess solvent is removed by distillation ln vacuo, and 25 the aluminium compound formed is decomposed with dilute sulphuric acid or sodium hydroxide solution. The further working-up is effected in a customary manner.
Prefarred acids for the preparation of acid addition alts of the azolyl-alkenones and -ols of the 30 -formula (I) are those which have already been mentioned in connection with the description of the acid addition salts according to the inv~ntion as being preferred acids.
The acid addition salts of the compounds of the formula (I) can be obtained in a simple manner according 35 to customary methods of salt formation, for example by Lz A 21 385 ~5~3~3 dissolving a compound of the formula (I) in a suitable inert solvent and adding the acid, for example hydro-chloric acid, ~nd can be isolated in a known manner, for example by Filtration, and can be purified, if appropriate, by washing with an inert organic solvent.
Preferred salts for the preparation of metal salt complexe~ of azolyl-alkenones and -ols of the formula (I) are salts of those anions and cations which have already been mentioned in connection with the description of the metal salt complexes according to the invention as being preferred.
The metal salt complexes of compounds of the for-mula (I) can be obtained in a simple manner according to customary processes, thus, for example, by dissolving the metal salt in an alcohol (such as ethanol), and adding the solution to the compound of the formula (I). The metal salt complexes can be isolated in a known manner, for example by filtration, and if appropriate purified by recrystallisation.
2û The active compounds according to the invention engage in the metabolism of the plants and can therefore be employed as growth regulators.
Experience to date of the mode of action of plant growth regulators has shown that an active compound can also exert several differen-t actions on plants. The actions of the compounds depend essentially on the point in time at which they are used, relative to the stage of development of the plant, and on -the amounts of active compound applied to the plants or their environment and the way in which the compounds are applied. In every case, growth regulators are intended to influence the crop plants in the particular manner desired.
Plant growth-regulating compounds can be employed, for example, to inhibit vegetative growth of the plants.
Such inhibition of growth is inter alia of economic inter-Lel~ 2~ 385 ~ ~S~$~

est in the case of gra~ses, since it is thereby possible to reduce the frequency of cutting the grass in ornamental gardens, parks and sportsgrounds, at verges, at airports or in fruit orchards. The inhibition of growth of herbaceous and woody plants at verges and in the vicinity of pipelines or overland lines or, quite generally, in areas in which heavy additional growth of plants is un-desired, is also of importance.
The use of growth regulators to inhibit the growth ln length of cereals is also important. The danger of lodging of the plants before harvesting is thereby reduced or completely eliminated. Furthermore, growth regulators can strengthen the stem of cereals, which again counter-acts lodging. Use of growth regulators for shortening and strengthening the stem enables higher amounts of fer-tiliser to be applied to increase the yield, without danger of the cereal lodging.
In the case of many crop plants, inhibition of the vegetative growth makes denser planting possible, so that grea-ter yields per area of ground can be achieved.
;~ An advantage of the smaller plants thus produced is also that the crop can be worked and harvested more easily.
Inhibition of the vegetative growth of plants can also leacl to increases in yield, sinca the nutrients and assimilates benefit blossoming and fruit formation to a greater extent than they benefit the vegetative parts of plants.
Promotion of vegetative growth can also frequently be achieved with growth regulators. This is oF great utility if it is the vegetative parts of the plants which are harvested. Promoting the vegetative growth can, how-ever, also simultaneously lead to a promotion of gener-ative growth, since more assimilates are formed, so that more fruit, or larger fruit, is obtained.
Increases in yield can in some cases be achieved Le A 21 385 ~ ~ ~15~

by affecting the plant metabolism, without noticeable changes in vegetative growth. A change in the composition of plants, which in turn can lead to a better quality of the harvested products, can furthermore be achieved with grow-th regwlators. Thus it is possible, for example, to increase the content of sugar in sugar beet, sugar cane, pineapples and citrus fruit or to increase the protein content in soya o~ cereals. Using growth regulators it is also possible, for example, to inhibit the degradation 1û of desired constituents, such as sugar in sugar beet or sugar cane, before or after harvesting. It is also possible favourably to influence the production of the efflux of secondary plant constituents. The stimulation of latex flux in rubber trees may be mentioned as an example.
Parthenocarpous fruit can be formed under the ; influence of growth regulators. Furthermore, the gender of the flowers can be influenced. Sterility of the pollen can also be produced, which is of great importance in the breeding and preparation of hybrid seed.
Branching of plants can be controlled by using growth regulators. On the one hand, by breaking the apical dominance the development of side shoots can be promoted, which can be very desirable, especially i.n the cultivation of ornamental plants, also in connection with growth inhibition. Qn the other hand, however, it is also possible to inhibit the growth of side shoots. There is great interest in this action, for example, in the culti-vation of tobacco or in the planting o~ tomatoes.
The amount oF leaf on plants can be controlled, ; under the influence of growth regulators, so that defoli-ation of the plants at a desired point in time is achieved.
Such defoliation is of great importance in the mechanical harvesting of cotton~ but is also of interest for facili-tating harvesting in other crops, such as in viticulture.

Le A 2~1 ~85 Defoliation of the plants can also be carried out to lowerthe transpiration of plants before they are transplanted.
The shedding of fruit can also be controlled with growth regulators. On the one hand~ it is possible to prevent premature shedding of fruit. However, on the other hand, shedding of fruit, or even the fall of blossom~
can be promoted up to a certain degree (thinning out) in order to interrupt the alternance. ~y alternance there is understood the peculiarity of some varieties of fruit to produce very different yields from year to year, for endogenir reasons. Finally, using growth regulators it is possible to reduce the force required to detach the fruit at harvest time so as to permit mechanical harvesting or facilitate manual harvesting.
Using growth regulators, it is furthermore possible ~ to achieve an acceleration or retardation of ripening - ` of the harvest product, before or after harvesting. This ~ is of particular advantage, since i-t is thereby possible ; to achieve op-timum adaptation to market requirements.
Furthermore, growth regulators can at timss improve the coloration of fruit. In addition, concentrating the ripening within a certain period of time is also achievable with the aid of growth regulators. This provides the preconditions for being able to carry out complete mechanical or manual harvesting in only a single pass, for example in the case of tobacco, tomatoes or coffee.
Using growth regulatorq, it is furthermore possible to influence the latent period of seeds or buds of plants, so that the plants, such as, for example, pineapple or ornamental plants in nurseries, germinate, shoot or blossom at a time at which they normally show no readiness to do so.
Retarding the shooting of buds or the germination of seeds with the aid of growth regulators can be desirable in regions where frost is a hazard, in order to avoid damage by late frosts.
:
Le A 21 ,385 .

Finally, the resistance of plan-ts ta frost, drought or a high salt content in the soil can be induced with growth regulators. Cultivation of plants in regions which are usually ~n~uita~le for this purpose thereby becomes possible.
The preferred time of application of the growth regulators depends on the climatic and vegetative circum-stances.
The foregoing description should not be taken as implying that each of the compounds can exhibit all of the describsd effects on plants. The effect exhibited by a compound ln any particular set of circumstances must be determined empirically.
The active compounds according to the invention also exhibit a powerful microbicidal action and can be employed in practice for combating undesired micro-organisms. The active compounds are suitable for use as plant protection agents.
Fungicidal agents in plant protection are employed for combatinS~ Plasmodiophoromycetes, Oomycetes, Chytridio-; mycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
The good toleration, by plants, of the active com-pound~, at the concentrations required -for combating plant diseases, permits treatment of above-ground parts of plants, of vegetative propagation stock and seeds, and of the soil.
As plant protection agents, the active compounds according to the invention can be used with particularly good success for combating those fungi which cause powdery mildew diseases, thus, For combating Erysiphe species, such as, for example, against the powdery mlldew of barley or of cereal causative oryanism (Erysiphe graminis)~ for combating stripe disease of barley (Drechsiera graminea), for combatin~ Venturia species~ such as, for example, Le A 21 335 against the apple scab causative organism (Venturia inaeq~alis), or for combating rice diseases, such as, ~or example, Pyricularia oryzae and Pellicularia sasakii.
The active compounds can be converted into the customary formulations, such as solutions, emulsions, sus-pensions, po~ders, foams, pastes, granules, aerosols, very fine capsules in polymeric substances and in coating compositions for seed, as well as ULV ~ormulations.
These formulations may be produced in known manner, for example by mixing the active compounds with extenders, tha-t is to say liquid or liquefied gaseous or solid diluents or carriers, optionally with the use of surface-active agents, that is to say emulsiFying agents and/or dispersing agents and/or foam-forming agents. In the case of the use of water as an extender, organic sol~ents can, -For example, also be used as auxiliary solvents.
As liquid diluents or carriers, especially solvents, there are suitable in the main, aromatic hydro-carbons, such as xylene, toluene or alkyl naphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chlor-ide, aliphatic or alicyclic hydrocarbons, such as cyclo-hexane or paraffins, for example mineral oil 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, or strongly polar solvents, such as dimethylformamide and dimethyl-sulphoxide, as well as water.
By liquefied gaseou~ diluents or carriers are meant liquids which would be gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.
As solid carriers there may be used ground natural minerals, such as kaolins, clays, talc, chalk3 quartz, Ls A 21 385 attapolgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as highly-dispersed silicic acid, alumina and silicates. As olid carriers for granules there may be used crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals) and granules of organlc material such as sawdust, coconut shells, maize cobs and tobacco stalks.
As emulsifying and/or foam-forming agents there may 10 be used non-ionic and anionic emulsifiers, such as polyoxy-ethylene-fat~y acid esters, polyoxyethylene-fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl ~ulphonates, alkyl sulphates, aryl sulphonates as well as albumin hydrolysis products. Dispersing agents include, 15 for example, lignin sulphite waste liquors and methyl-~ cellulose.
; Adhesives such as carboxymethylcellulose and nat-ural and synthetic polynlers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol 20 and polyvinyl acetate, can be used in the Formulations.
It is possible to use colorants such as inorganic pigments, for example iron oxida, titanium oxide and Prussian 31ue, and organic dyest~ffs~ such as alizarin dyestuffs, azo dyestuffs or metal phthalocyanine dyestuffs, 25 and trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and ~inc.
The formulations in yeneral contain from 0.1 to 95 per cent by weight of active compound, preferably from 0.5 to 90 per cent by weight.
The active compounds according to the invention can be present in the formulations as a mixture with other known ac~ive compo~nds, such as fungicides, insecticides, acaricides and herbicides, and also as mixtures with fer-tilisers and other growth regulators.
The active compounds can be used as such, in the Le A 21 ~85 -form of their formulations or as the use forms prepared therefrom, such as ready-to-use solutions, emulsifiable concentrates, emulsions,foams, suspensions, wettable powders, pas~es, soluble powders, dusting agents and granules. rhey are used in the customary manner, for example by watering, spraying, atomising, scattering, - dusting, foaming or coating. Furthermore, it is possible to apply the active compounds in accordance with the ultra~low volume process or to inject the active compound preparation or the active compound itself into the soil. It is also possible to treat the seed of plants.
When the compounds according to the invention are employed as plant growth regulators, the amoun-ts applied can be varied within a relatively wide range.
In general, O.Ol to 5û kg, preferably 0.05 to lO kg, are employed per hectare of soil surface.
When the substances according to the invention are employed as fungicides, also, the amount applied can be varied within a relatively wide range, depending on the type Df application.
Thus, especially in the treatment of parts of plants, the active compound concentrations in the use forms are in general between l and 0. 000lo by weight 25 preferably between 0.5 and O.OOlJo by weight.
In the treatment of seed, amounts of active compound oF O.OOl to 50 9 per kg of seed, preferably O.Ol to lû 9, are generally required.
In the treatment of soil, active compound concentrations of O.OOOOl to 0.16 by weight, preferably û.OOOl to 0.02o~ are generally required at the place of action~
The present invention also provides plant growth regulating or fungicidal composition containing as active ingredient a compound of the present invention in admixture Le A.21..385 .:
' with a solid or liquefied gaseous diluen-t or carrier or in adrnixture with a liquid diluent or carrier containing a surface-active agent.
The present invention also pro~ides a method of com-bating fungi which comprises applying to the fungi, or toa habitat thereof, a compound of the present invention alone or in the form of a composition containing as active ingredient a compound of the present invention in admixture with a diluent or carrier.
The present invention also provides a method of rogulating the growth of plants which cornprises applying to the plants, or to a habitat thereof, a compound of the present invention alone or in the form of a composition containing as active ingredient a compound of the present in~ention in admixture with a diluent or carrier.
The present invention further provides crops protected from damage by fungi by being grown in area~ in which immediately prior to and/or during the time of the growing a compound of the present invention was applied alone or in admixture with a diluent or carrier.
The prssent invention further provides plants, the growth of which has been regulated by their being grown in areas in which immediately prior to and/or during the time of tho growing a compound of tha presant invention was applied alone or in admixture with a diluent or carrier.
It will be seen that the usual methods of providing a harYested crop may be improved by the present inven-tion.
The Example: which follow illustrate the prepar-ation of the substqnces according to the present invention.
3n Preparative E_amples Example l ~ N (l) N

Le,A 21,~85 ... . .. _ _ a~

- 2~ -20 g (0.073 mol) of 6-cyclohexyl-2,2-dimethyl-4-(1,2~4-triazol-1-yl)-hex-4-en-3-one and 2~ 9 of aluminium oxide in 300 ml of methanol were heated under ~eflux for 24 hours. The reaction mixture was ~llowed to cool and was Filtered under suction over kieselguhr, and the fil-; trate was concentrated. 19~9 9 (99O of theory) of 6-cyclohexyl-2,2-dimethyl-4-(1,2,4-triazol-1-yl)-hex-5-en-

3-one of refractive index nD = 1~4890 were obtained.
Preparation of the starting material ________________________~___________ r-~
a) (CH3)3C - C0 - C = CH - CH
~ N~N

44.4 9 (0.2 mol) of 2,2-dimsthyl-5-dimethylamino-~ 4-(1,2,4-triazol-1-yl)-pent-4-en-3-one were dissolved in ; 600 ml oF ether, and a solution of 48.2 9 (0.24 mol) of - cyclohexylmethyl-magnesium bromide in 200 ml of ether was added at -20C. Stirring was continued for 1.5 hours, the reaction mixture was adjusted to a pH value of from 7 to 8 with dilute hydrochloric acid. Thereafter, the organic phase was separated off, washed twice with water, dried ; over sodium sulphate and concentrated. 27.4 9 (49.8~ of theory) of 6-cyclohexyl-2,2-dimethyl-4-(1,2,4-triazol-1-;~ yl)-hex-4-en-3-one of reFractive index nD = 1.4910 were obtained.

-(CH3)3C - C0 - C = CH - N(CH3)2 b) ~ N`N
N LJ

250.8 9 (1.5 mol) of 2,2-dimethyl-4-(1,2,4-triazol-1-yl)-butan-3~one were heated under reflux with 196 9 (1.65 mol) oF dimethylformamide di~ethylacetal for 5 hours~

Le A 21 -385 i .

Thereafter, the excess acetal was distilled off. 306 g (92~o of theory) of 2,2-dimethyl-5-dimethylamino-4~(192,4-triazol-l-yl)-pent-4-en-3 one of refractive index nD =
1.531 were obtained.

c) (CH3)3C - CO - C~2 - N ~

138 g (2 mol) of 1,2,4-triazole were added in portions to 276.4 g (2 mol~ of ground potassium carbonate and 296.2 g (2 mol) of ~-chloropinacolin in 500 ml of acetone at room temperature, the internal temperature increasing to the boiling point. The mixture was stirred - under reflux for 5 hours and was then cooled to room tem-perature. The reaction mixture was filtered, and the fil-trate was concentrated by distilling off the solvent in vacuo. The oily residue crystallised after the addition of naphtha. 240.8 g (72% of theory) of 2,2-dimethyl-4-(1,2,4-triaæo:L-l-yl)-butan~3-one^of melting point 62 to 64C were obtained.
Example 2 OH
CH - CH = CH ~ (2) N ~
10.~ g (0.038 mol) of 6-cyclohexyl-2,2-dimethyl-

4-(1,2,4-kriazol-1-yl)-hex-5-en-3-one (obtained as described in Example 1) were dissolved in 100 ml of methanol, and a ; solution of 0.38 g (0.01 mol) of scdium borohydride in 5 ml of ice-~ater was added dropwise at -10C. Stirring was continued for a further 2 hoursl and the reaction mixture was then ad~ustecl to a pH value of from 6 to 7 with dilute hydrochloric acid. The reaction mixture was Le ~ 21 385 :

concentrated by distilling off the solvent in vacuo.
The residue was taken up in methylene chloride, and the solution was washed with water, dried over sodium sulphate and concentrated. 8.9 g (86% of theory) of S-cyclohexyl-

5 2,2-dimethyl-4-(1,294-triazol-1-yl)-hex-5-en-3 ol of refractive index nD = 1.4920 were obtained.
The following compounds of the formula (I) were obtained in a corresponding manner and according to the processes given:
Table 2 R 1 _ X - CH - CH = CH - R;~
~N~y (I) N 1¦
Melting point Example 1 2 (C), refract-No. R X Y R ive index n~
( 3)3 C0 N C6H13 1.5388 ( 3)3 C0 7 15 1.4778 ( 3)3 C0 3 7 1.4880 Cl

6 (CH3)3c- C0 N ~ Cl 105-108

7 (CH3)3c- C0 N ~ Cl 1.5512

8 (CH3)3c- C0 N -i-C3H7 1.4871 ( 3)3 C0 2 3 7 8 (CH3)3c- C0 N - ~ F 1.5434 ~ C 1 11 (CH3)3C-- C0 N ~ -Cl 138-140 Cl~
12 (CH3)3c- C0 N ~ 1.5624 Cl/
13 (CH3)3C- C0 N -CH(C2H5)2 1.4885 Le A 21 385 `: -Table 2 (continuation) r~lelting point Examp le 220 No.Rl X Y. R. . .i.ve. in.dex. nD
14ClCH2C(CH3)2- CO N -CH2-i-C3H7 1.4969 15FCH2C(CH3)~- CO N -CH2-i C3 7 1.4777 16(CH3)3c- CH(OH) N - ~ ~ Cl viscous oil 17(CH3)3c- CH(OH) N -C3H7 1.4898 18(CH3)3c- CH(OH) N C6H13 1.4798 19(CH3)3c- CH(OH) N ~ Cl 1.5633 203)3 CH(OH) N -i-C3H7 1.4841 21( 3)3 CH(OH) N -CH2-i-C3H7 1.4857 22(CH3)3c- CH(OH) N -C7H15 1.4807 23(CH3)3c- CH(OH) M ~ F 112-124 Cl 243)3 CH(OH) N - ~ Cl (A form) 25(CH3)3c- CH(OH) N ~ Cl 46-48 26(CH3)3c- CH(OH) N ~ 180 (A form) Cl 27(CH3)3c- CH(OH) N -CH(C2H5)C4H9 1.4832 28( 3)3 CH(OH) N -CH(C2H5)C4H9 1.4832 29ClCH2C(CH3)2- CH(OH) N -CH2-i-C3H7 1.500].
30 FCH2C(CH3)2- CH(OH) N -CH2-i C3H7 1.4852 31 Cl- ~ CH(OH) N ~ 50-60 32 (CH3)3C- CO CH -C3H7 1.4915 Le A 21 385 .

Table 2 (continuaticnj Melting point Example (C), refractive No. Rl X Y R2 index n20 3)3 CO C6H13 1.4773 34 (CH3)3C- CO CH -C7H13 1.4808 ( 3)3 CO CH C8H17 1.4742 36 (CH3)3C- CO CH -C9Hl9 1.4770 7 ( 3)3 CO C~ -C5Hll 1.4890 Cl 38 ( 3)3 CO CH ~ ,-Cl viscous oil 39 - (CH3)3C- CO CH - ~ 1.5018 (CH3)3C- CO 5 11 1.4892 Cl 41 (CH3)3c- CH(OH) CH - ~ Cl 92-96 42 (CH3)3C- CH(OH) CH ~C6Hl3 1.4742 43 (CH3)3C- CH(OH) CH ~ 1.5050 44 Br- ~ r CO N @` 46 Br ~ ~ CO N ~ 107-111 ( X CUC 12 ) :: :
46 C3H7-C(CH3)2- CH(OH) N -CH2-i-C3H7 1.4849 A form and B form ~ the two possible geometric isomers 47 CH30-~ ~ CH(OH) N C2H5 1.5320 (A
48 (CH3)3C- CO N -CH2-C(CH3)3 1.4828 49 (C~I3)3C- CO N -CH2 ~ 1.4884 5 (CH3)3C- CH(OH) N -CH2 ~ 1.4887 51 (CH3)3C- CH(OH) N -CH2-C(CH3)3 62 52 C1- ~ CH(OH) N -CH2-i-C H 49 53 CH30 ~ CH(OH) N C2H5 Lio (B form) : ` ~
54 Cl ~ CH(OH) N C2H5 67 Le A 21 385 :`
.

Table ~ (conti.nuation) Melting point (C), rer~c-tive Example 1 2 20 No. R X Y R index nD
C3H7-C (CH3) 2- CO N -CH2-C3E~7-i 1 . 4819 56 (CH3) 3C- CO 2 ( 3) 2H5 3 ) 3 CH ( OH ) N -CH2-CH (C~13) -C2H5 1 4 81 9 ~: 58 Cl~O~ CO N CH3 1 . 5996 The plant growth regulating and fungici.dal activity of the compounds of this invention is illustrated by the following biotest Examples.
In these Examples, the compounds according to the present invention are each identified by the number (given in brackets) of the correspon~ing preparative Example.
~ he known comparison compounds are identified as ollows:

(A) = (CH3)3C-~H-CH-CH=C

:~ 0 ; ~ (CH3)3C-CH-CH-CH
(B) = ~ N~N
: : N l¦

OH ,CH3 (C) = (CH3)3C-CI - IH-CH=C~

OH
(D) (CH3)3C-CH-~H-CH= ~

N ~ x H2SO4 `; :
(E) - (CH3)3C-CO-CH-CH= ~
N~N CH3 N l¦
Le ~ 21 385 _ , . ... . . ... . ..... . . . . . . . . . . .

Example A
Inhibition of growth o~ soya ~eans Solvent: 30 parts by weight of dimethylformamide ~mulsifier: 1 part by weight of polyoxyethylene sorbitane monolaurate To produce a suitable preparation of active com-pound, 1 part by weight of active compound was mixed with the stated amounts of solvent and ernulsifier and the mix-ture was made up to the desired concentration with water.
Soya bean plants were grown in a greenhouse until the first secondary leaf had unfolded completely. In this stage, the plants were sprayed with the preparations of active compound until dripping wet. After 3 weeks, the additional growth was measured on all the plants and the inhibition of growth in per cent of the additional growth of the control plants was calculated. 100~ inhi-bition of growth meant that growth had stopped and 0%
denoted a growth corresponding to that of the control plants.
In this test, the active compounds (21) and (19) according to the in~ention showed a better inhibition of growth than the compound (~) which is known from the prior art.
Example B
Inhibition of growth of grass (Festuca pratensis) Solvent: 30 parts by weight of dimethylformamide Emulsifier: 1 part by weight of polyoxyethylene sorbitane monolaurate ~o produce a suitable preparation of active com-3 pound, 1 part by weight of active compound was mixed withthe stated amounts of solvent and emulsifier and the mix-ture was made up to the desired concentration with water.
Grass (Festuca pratensis) was grown in a green~
house up to a height in growth of 5 cm. In this stage, the plants were sprayed with the preparations of active Le A 21 385 5~

compound until dripping wet. After 3 weeks, the additional growth was measured and the inhibition of growth in per cent of the additional growth of the control plants was calculated. 100% inhibition of growth meant that growth had stopped and 0% denoted a growth corresponding to that of the control plants.
In this test, the active compound (21) according to the invention showed a substantially better inhibition of growth than the compounds (A) and (B) which are known from the prior art.
Example C
Influence on_growth of sugar beet Solvent: 30 parts by weight of dimethylformamide Emulsifier: 1 part by weight of polyoxyethylene sorbitane monolaurate To produce a suitable preparation of active com-pound, 1 part by weight of active compound was mixed with the stated amounts of solvent and emulsifier and the mixture was ~.ade up to the desired concentration with water.
Sugar beet was grown in a greenhouse until f`orm-ation of the cotyledons was complete. In this stage, the plants were sprayed with the preparation of active com-pound until dripping wet. After 14 days, the additional growth of the plants was measured and the influence on growth in per cent of the additional growth of the con-trol plants was calculated. 0% influence on growth denoted a growth which corresponded to that of the control plants. Negative values characterised an inhibition of growth in comparison to the control plants, whilst positive values characterised a promotion of growth in comparison to the control plants.
In this test, the active compounds (16), (1&), (19), (21), (26), (36) and (41) according to the invention had a greater influence on growth than the compounds (C) and (D) 1e_A 21 385 G`.~

known from the prior art.
Exam In~ibition of growth of cotton Solvent: 30 parts by weight of dimethylformamide Emulsifier: l part by weight of polyoxyethylene sorbitane monolaurate To produce a suitable preparation of active com-pound, 1 part by weight of active compound was mixed with the stated amounts of solvent and emulsifier and the mixture was made up to the desired concentration with water.
Cotton plants were grown in a greenhouse until the 5th secondary leaf had unfolded completely. In this stage, the plants were sprayed with the preparations of act-ive compound until dripping wet. After 3 weeks, theadditional growth of the plants was measured and the inhibition of growth in per cent of the additional growth of the control was calculated. 100% inhibition of growth meant that growth had stopped and 0% denoted a growth corresponding to that of the control plants.
~ In this test, the active compounds (1~, (6), (10), ; (11), (16) and (25) according to the invention show a better inhibition of growth than the compounds (A), (B) and (E) known ~rom the prior art.
Example E
2 in soya beans Solvent: 30 parts by weight of dimethylformamide Emulsifier: 1 part by weight of polyoxyethylene sorbitane monolaurate To produce a suitable preparation of active com-pound, l part by weight of active compound was mixed with the stated amounts of solvent and emulsifier and the mixture was made up to the desired concentration with water.
Soya bean plants were grown in a greenhouse until :
Le A 21 385 , the first secondary leaf had completely unfolded. At this stage, the plants were sprayed with the preparations of active compound until dripping wet. In the further course of the experiment, the fixation of C02 in the plants was determined by customary methods. The values were compared with those of the control plants which had not been tr-eated with the active compounds.
The figures of merit had the following meanings:
denoted inhibition of the fixation of C02 0 denoted fixation of C02 as in the case of the control + denoted low stimulation of the fixation of C02 ~+ denoted powerful stimulation of the fixation of C02 ~++ denoted very powerful stimulation of the fixation f C2 In this test, the active compounds (1) a~ld (22) according to the invention showed stimulation of the fixat-ion of C02~ in contrast to the compounds (A), (B) and (E) known from the prior art.
ExamPle F
_ _ Erysiphe test ~
Solvent: 100 parts by weight of dimethylformamide Emulsifier: 0.25 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active com-pound, 1 part by weight of active compound was mixed with the stated amounts of solvent and emulsifier, and the concentrate was diluted with water to the desired conc-; entration.
To test for protective activity, young plants were ; sprayed with the preparation of active compound until dew-moist. After the spray coating had dried on, the plants were dusted with spores of Erysiphe graminis f.sp. hordei.
The plants were placed in a greenhouse at a temper-ature of about 20C and a relative atmospheric humidity of I.e A 21 385 about 80%, in order to promote the development of powdery mildew pustules.
~val~ation was carried out 7 days after the inoculation.
In this test, a clearly superior activity com-pared with the compound (E) known ~rom the prior art was shown, for example, by the compounds (5), (32), (34)7 (35), (36), (4G), (42), (38), (~), (17), (18) 3 ( 19), (20), (21), (22)~ (10), (11), (25) and (12).
10 ~
Drechslera graminea test (barley)/seed treatment (syn. Helminthosporium gramineum) The active compounds were used as dry dressings.
These were prepared by extending the particular active com-pound with a ground mineral to give a finely pulverulent mixture, which ensured uniform distribution on the seed surface.
To apply the dressing, the infected seed was shaken with the dressing in a closed glass flask for 3 minutes.
The seed was embedded in sieved, moist standard soil and was exposed to a temperature of 40C in closed Petri dishes in a refrigerator for 10 days. Germination of the barley, and possibly also of the fungus spores, was thereby initiated. 2 batches of 50 grains of the pregerminated barley were subsequently sown 3 cm deep in standard soil and were cultivated in a greenhouse at a temperature of about 18C in seedboxes which were exposed to light for 15 hours daily.
About 3 weeks after sowing, the plants were evaluated 3 for symptoms of stripe disease.
In this test, a clearly superior activity compared with the compound (B) known from the prior art was shown, for example, by the compounds (17) and (21).

Le A 21 385 .. .. ... ... . . .

Claims (32)

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:

1. An azolyl-alkenone or -ol of the general formula I

in which R1 represents an alkyl radical, a halogenoalkyl radical or a phenyl radical, which phenyl radical is optionally monosub-stituted or polysubstituted by identical or different substituent(s) selected from halogen, alkyl having 1 to 4 carbon atoms, alkoxy and alkylthio, each having 1 to 4 carbon atoms, alkylamino and dialkylamino, each having 1 to 4 carbon atoms in each alkyl part, and also halogenoalkyl, halogenoalkoxy and halogenoalkylthio, each having 1 or 2 carbon atoms and 1 to 5 identical or different halo-gen atoms, phenyl and phenoxy, it being possible for the two last-mentioned radicals in turn to be substituted by halogen and/or alkyl having 1 or 2 carbon atoms; R2 represents an alkyl radical, a phenyl radical, which phenyl radical is optionally monosubsti-tuted or polysubstituted by identical or different substituents selected from halogen, alkyl having 1 to 4 carbon atoms, alkoxy and alkylthio, each having 1 to 4 carbon atoms, alkylamino and dialkylamino, each having 1 to 4 carbon atoms in each alkyl part, and also halogenoalkyl, halogenoalkoxy and halogenoalkylthio, each having 1 or 2 carbon atoms and 1 to 5 identical or different halo-gen atoms, phenyl and phenoxy, it being possible for the two last-mentioned radicals in turn to be substituted by halogen and/or alkyl having 1 or 2 carbon atoms, a cycloalkyl radical, which cyclo-alkyl radical is optionally substituted by halogen and/or alkyl having 1 to 4 carbon atoms or a cycloalkylalkyl radical, which cycloalkylalkyl radical is optionally substituted by halogen and/or alkyl having 1 to 4 carbon atoms; X represents a CO or CH(OH) group; and Y represents a nitrogen atom or a CH group; and the acid addition salts and metal salt complexes thereof.

2. A compound according to claim 1, in which R1 represents a grouping of the general formula z1 and z2 are identical or different and represent a hydrogen or halogen atom or an alkyl radical having 1 to 4 carbon atoms, and furthermore R1 represents a phenyl radical which can be monosub-stituted or polysubstituted by identical or different substituent(s) selected from halogen, alkyl having 1 to 4 carbon atoms, alkoxy and alkylthio, each having 1 to 4 carbon atoms, alkylamino and dialkylamino, each having 1 to 4 carbon atoms in each alkyl part, and also halogenoalkyl, halogenoalkoxy and halogenoalkylthio, each having 1 or 2 carbon atoms and 1 to 5 identical or different halo-gen atoms, phenyl and phenoxy, it being possible for the two last-mentioned radicals in turn to be substituted by halogen and/or alkyl having 1 or 2 carbon atoms, R2 represents a straight-chain or branched alkyl radical having 1 to 12 carbon atoms, and also repre-sents a phenyl radical which can be monosubstituted or polysubstituted by identical or different substi-tuents selected from halogen, alkyl having 1 to 4 carbon atoms, alkoxy and alkylthio, each having 1 to 4 carbon atoms, alkylamino and dialkylamino, each having 1 to 4 carbon atoms in each alkyl part, and also halogeno-alkyl, halogenoalkoxy and halogenoalkylthio, each having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms, phenyl and phenoxy, it being possible for the two last-mentioned radicals in turn to be substituted by halogen and/or alkyl having 1 or 2 carbon atoms, or R2 represents a cycloalkyl radical which has 3 to 7 carbon atoms and is optionally substituted by halogen and/or alkyl having 1 to 4 carbon atoms, or represents a cycloalkylalkyl radical which has 3 to 7 carbon atoms in the cycloalkyl part and 1 or 2 carbon atoms in the alkyl part and is optionally substituted by halogen and/or alkyl having 1 to 4 carbon atoms.

3. Compounds according to claim 1, in which R1 represents a grouping of the general formula Z1 and Z2 are identical or different and repre-sent a hydrogen, fluorine, chlorine or bromine atom or a methyl, ethyl, propyl or butyl; or R1 represents a phenyl radical which is optionally mono-substituted to trisubstituted by identical or different substituents selected from fluorine, chlorine, methyl, isopropyl, tert.-butyl, methoxy, methylthio, isopropoxy, trifluoromethyl, trifluoro-methoxy, trifluoromethylthio, methylamino, dimethyl-amino, and phenoxy or phenyl optionally substituted by fluorine, chlorine or methyl;
R2 represents a straight-chain or branched alkyl radical having 1 to 8 carbon atoms, or a phenyl which is optionally monosubstituted to trisubsti-tuted by identical or different substituents selected from fluorine, chlorine, methyl, isopropyl, tert.-butyl, methoxy, methylthio, isopropoxy, trifluoro-methyl, trifluoromethoxy, trifluoromethylthio, methylamino, dimethylamino, and phenoxy or phenyl optionally substituted by fluorine, chlorine or methyl, and R2 furthermore represents a cyclopropyl, cyclo-butyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexyl-methyl radical, each of which is optionally substi-tuted by methyl, ethyl, isopropyl, fluorine or chlorine.

4. A compound according to claim 1, wherein X is CO.

5. A compound according to claim 1, wherein X is CH(OH).

6. A compound according to claim 1, wherein Y is a nitrogen atom.

7. A compound according to claim 1, wherein R1 is (CH3)3C-.

8. A compound according to claim 7, wherein Y is a nitrogen atom.

9. A compound according to claim 8, wherein X is CO.

10. A compound according to claim 8, wherein X is CH(OH).

11. 6-Cyclohexyl-2,2-dimethyl-4-(1,2,4-triazol-1-yl)-hex-5-en-3-one of the formula

12. 6-[2,4-Dichlorophanyl)-2,2-dimethyl-4-(1,2,4-triazol-1-yl)-hex-5-en-3-ol of the formula

13. 2,2,8,8-Tetramethyl-4-(1,2,4-triazol-1-yl)-oct-5-en-3-ol of the formula

14. 2,2-Dimethyl-4-(1,2,4-triazol-1-yl)-tridec-5-en-3-ol of the formula

15. A process for the production of a compound according to claim 1, characterised in that a compound of the general formula (II) in which R1, R2 and Y have the same meanings as in claim 1, is heated in the presence of a diluent and, if a compound of formula (I) according to claim 1 is required in which X
represents a CH(OH) group, the resulting azolyl-alkenone according to claim 1 of the general formula (Ia) in which R1, R2 and Y have the same meanings as in claim 1, is reduced; and, if required, an acid or a metal salt is then added onto the compound according to claim 1 produced by the foregoing process.

16. A method for combating fungi which comprises applying to the fungi, or to the habitat thereof, a fungicidally effective amount of a compound of claim 1.

17. A method according to claim 16 wherein the compound is applied in the form of a composition containing the compound as active ingredient, in admixture with a suitable diluent or carrier.

18. A method according to claim 16, wherein said compound is applied in an amount of 0.0001% to 1% by weight.

19. A method according to claim 16 or 17, wherein said com-pound is applied in an amount of 0.001 to 0.5% by weight.

20. A method according to claim 16 or 17, wherein said com-pound is applied to soil in an amount of 0.0001 to 0.02% by weight.

21. A method according to claim 16 or 17, wherein said com-pound is applied to seed in an amount of 0.001 to 50 g per kg of seed.

22. A method according to claim 16, 17 or 18, wherein the compound is 6-cyclohexyl-2,2-dimethyl-4-(1,2,4-triazol-1-yl)-hex-5-en-3-one.

23. A method according to claim 16, 17 or 18, wherein the compound is 6-(2,4-dichlorophenyl)-2,2-dimethyl-4-(1,2,4-triazol-1-yl)-hex-5-en-3-ol.

24. A method according to claim 16, 17 or 18, wherein the compound is 2,2,8,8-tetramethyl-4-(1,2,4-triazol-1-yl)-oct-5-en-3-ol.

25. A method according to claim 16, 17 or 18, wherein the compound is 2,2-dimethyl-4-(1,2,4-triazol-1-yl)-tridec-5-en-3-ol.

26. A method of regulating the growth of plants which com-prises applying to the plants, or to a habitat thereof, a plant growth regulating effective amount of a compound according to claim 1.

27. A method according to claim 26, wherein the compound is added in the form of a composition containing the compound as active ingredient, in admixture with a suitable carrier or diluent.

28. A method according to claim 26, wherein said compound is applied to an area of agriculture in an amount of 0.01 to 50 kg per hectare.

29. A method according to claim 26, 27 or 28, wherein the compound is 6-cyclohexyl-2,2-dimethyl-4-(1,2,4-triazol-1-yl)-hex-5-en-3-one.

30. A method according to claim 26, 27 or 28, wherein the compound is 6-(2,4-dichlorophenyl)-2,2-dimethyl-4-(1,2,4-triazol-1-yl)-hex-5-en-3-ol.

31. A method according to claim 26, 27 or 28, wherein the compound is 2,2,8,8-tetramethyl-4-(1,2,4-triazol-1-yl)-oct-5-en-3-ol.

32. A method according to claim 26, 27 or 28 wherein the compound is 2,2-dimethyl-4-(1,2,4-triazol-1-yl)-tridec-5-en-3-ol.