NZ202416A - Diazoles and triazoles and fungicidal compositions - 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

New Zealand Paient Spedficaiion for Paient Number £02416 HQ N.Z. No COMPLETE SPECIFICATION Patents Act, 1953 NEW ZEALAND "Azolyl-alkenones and -ols, a process for their preparation, and their use as plant-growth regulators and fungicides." We, BAYER AKTIENGESELLSCHAFT, a Company registered under the laws of the Federal Republic of Germany, of Leverkusen, Germany, do hereby declare the invention, for which we pray that a Patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement:- (Followed by 1A.) 202416 - 1/) - Type la The present invention relates to certain new azolyl-alkenones and -ols, to a process for their production, and to their use as plant-growth regulators and fungicides.

It has already been disclosed that certain 6,6-disubstituted 2,2-dimethyl-4-(l,2,4-triazol-1-yl)-hex-5-en-3-ones and -ols possess good plant growth-regulating and fungicidal properties (see United Statesj;E&tent Specification) 4,315,764). However, the action of these compounds is not always completely satisfactory, in particular when low amounts and concentrations are used.

The present invention now provides, as new compounds, the azolyl-alkenones and -ols of the general formula R1 - X - CH - CH = CH - R2 ' (I) N U in which 1 R represents an alkyl, halogenoalkyl or optionally substituted phenyl radical, 2 R represents an alkyl , optionally substituted phenyl, optionally substituted cycloalkyl or optionally substituted cycloalkylalkyl radical, 20 X represents a CO or CH(OH) group, and V represents 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 25 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 double bond, the configuration Z (derived from jg "zusammen" (together)) is present, and if they are located I si A Q1 JO ji /. '\y, on opposite sides, the configuration E (derived from "entgegen" (opposed)) is present.

In addition, when X=CH(0H), the compounds according to the invention, of the formula (I)5 possess two 5 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 10 production of a compound of the present invention, characterised in that a compound of the general formula R1 - CO - C = CH - CH2 - R2 (II) A N I] in which 1 2 R , R and Y have the meanings given above, 15 is heated in the presence of a diluent and, if appropriate, in the presence of a catalyst or in the presence of aluminium oxide, and, if a compound in which X represents a CH(OH) group is required, the resulting azolyl-alkenones according to the 20 invention, of the general formula R1 - CO - CH- CH = CH - R2 | (la) N^» in y in which 1 2 R , R 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- alkenones and -ols of the formula (I), and their acid addition salts and metal salt complexes, possess powerful plant growth-regulating properties and powerful fungicidal properties.

In addition, the new azolyl-alkenones and -ols of the formula (I) are interesting intermediate products for the preparation of further plant protection agents.

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. By appropriate reactions, it is also possible to obtain functional derivatives of the keto group, such as oximes and oxime-ethers, hydrazones and ketals. The hydroxyl group of the carbinol derivatives can be converted into the corresponding ethers in a customary manner. Furthermore, .acyl derivatives of carbamoyl derivatives 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 invention possess a better plant growth-regulating and fungicidal action than the 6,6-disubstituted 2,2-dimethy1-4-(1, 2,4-triazol-1-y1)-hex-5-en-3-ones and -ols which are known from the prior art and are similar compounds chemically and with regard to their action. The active compounds according to the invention thus represent an enrichment of the art.

Preferred compounds according to the present invention are those in which 1 R represents a grouping of the general formula /CH221 -Cx"CH3 , XCH2Z2 wherein 1 2 Z and Z are identical or different and represent a hydrogen or halogen atom or an alkyl radical having 1 to 4 carbon atoms; or R represents a phenyl radical which is optionally 5 monosubstituted or polysubstituted (the substit- uent(s) thereon preferably being 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 10 carbon atoms in each alkyl part, and also halo genoalkyl, halogenoalkoxy and halogenoalkylthio , each having 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms, such as fluorine atoms and chlorine atoms, and phenoxy and phenyl 15 optionally substituted by halogen and/or alkyl having 1 or 2 carbon atoms); 2 R represents a straight-chain or branched alkyl radical having 1 to 12 carbon atoms; phenyl which is optionally monosubstituted or polysubstitited by identical or different substituents (the substituent(s ) thereon preferably being 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 halogen atoms, such as fluorine atoms and chlorine atoms, and phenoxy and phenyl option- ally substituted by halogen and/or alkyl having 1 or 2 carbon atoms); and furthermore 2 R preferably represents a cycloalkyl or cyclo-alkylalkyl radical which is optionally monosub-35 stituted or polysubstituted by identical or different 2024)6 substituents and each of which has 3 to 7 carbon atoms in the cycloalkyl part and 1 or 2 carbon atoms in each alkyl part (the following being mentioned as preferred substituents: alkyl having 5 1 to 4 carbon atoms and halogen), X represents a CO or CH(OH) group and Y represents a nitrogen atom or a CH group. Particularly preferred compounds of the present invention are those 10 in which i R represents a grouping of the general formula /CV1 -C-CH , \ 2 XCH2Zz wherein 1 2 Z and Z are identical or different and repre- sent a hydrogen, fluorine, chlorine or bromine atom or a methyl, ethyl, propyl or butyl; or R^" represents a phenyl radical which is optionally monosubstituted to trisubstituted by identical or different substituents selected from fluorine, 2q 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; 2 R represents a straight-chain or branched alkyl radical having 1 to 8 carbon atoms, or a phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents selected from fluorine, chlorine, methyl, isopropyl, 2Q tert.-butyl, methoxy, methylthio, isopropoxy, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, methylamino, dimethylamino, and phenoxy or phenyl optionally substituted by fluorine, chlorine or methyl; and 2 R furthermore represents a cyclopropyl, cyclo- butyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclo-hexylmethyl radical, each of which is optionally substituted by methyl, ethyl, 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 compounds mentioned in the preparative Examples, the following compounds of the general formula (I) may be mentioned individually (wherein X represents the CO or the CH(OH) group and Y represents a nitrogen atom or the CH group): Table 1 r1 - x - ch - ch = ch - r2 (I) r1 r2 ch2f h3c- c-ch2f -ch2-ch(ch3)2 ch2c1 h3c-c- -CH2-CH(CH3)2 ch2c1 (ch3)3c- (ch3)3c- J-.e (ch3)3c- -ch2^h (ch3)3c- -ch2-^hj> (ch3)3c- -ch2-ch(ch3)c2h5 (ch3)3c- -ch2-ch(ch3j c3h7 (ch3)3c- -ch2-ch(ch3)c<*h9 (ch3)3c- -ch2-c(ch3)3 (ch3)3c- -ch2-ch(c2hs)2 (ch3)3c- -ch2-ch(c3h7)2 ch3 (ch3)3c- -ch2 ch3 (ch3)3c- _ch2VA ch3 (ch3)3c- -ch2\(7) ch3 (ch3)3c- -ch2\jj> (ch3)3c- -ch(ch3)-ch(ch3)2 (ch3)3c- -c(ch3j2-ch(ch3)2 ocf3 (ch3 )3c- (ch3)3c- ^S>-oscr3 (ch3)3c- ^gy0ch3 (ch3)3c- "{qvc1 ch3 Table 1 (continuation) 1 2 R 1 ■ R "7 (CH3 ) jC- (ch3)3c- c1 (ch3)3c- ^l^c1 ci (ch3)3c- ^ch3 h3c ( c h 3 ) 3 c - ^g^c(ch3)3 (CH3)3C- ^gyCF3 & cf3 (CH3)3C- vqvN(CH3) (ch3)3c- yq\-sch; CI ch'3 (ch3)3c- ~c^c1 ch3 (ch3)3c- ^ ch; Cl' 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 R , 2 R , X and Y have the respective meanings which have already been mentioned in respect of preferred and particularly preferred compounds of the invention. . m • The acids which can be used to form adducts include, as preference, hydrohalic acids (such as hydrobromic acid and, especially, hydrochloric acid), phosphoric acid, nitric acid, sulphuric acid, monofunctional 5 and bifunctional carboxylic acids and hydroxycarboxylie acids (such as acetic acid, 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 10 acid).

Preferred compounds according to the invention 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) 1 2 in which R , R , X and Y have the respective meanings which have already been mentioned in the description of preferred and particularly preferred compounds of the invention.

Amongst these salts, salts of copper, zinc, manganese, magnesium, tin, iron and nickel are particularly 20 preferred. Suitable anions of these salts are those which are derived from those acids which produce physiologically tolerated addition products. Particularly preferred acids of this type, in this connection, are hydrohalic acids (such as hydrochlic acid and hydrobromic acid), 25 and also phosphoric acid, nitric acid and sulphuric acid.

If, for example, 6-cyclohexyl-2,2-dimethy1-4-(1,2,4-triazol-1-y1)-hex-4-en-3-one is used as the starting material, aluminium oxide is used as a reactant and methanol is used as the diluent, the course of the reaction according 30 to the process of the invention can be represented by the following equation: ' ■'■■'■foiiwft'rt"1 th n » 202416 /_x a12o3/ch3oh (ch3)3C-C0-C = ch-CH2-/h y > y y (ch3)3c-c0-(j!h-ch=ch-/h ff^N n y If, for example, 6-cyc1ohexy1-2 , 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: (ch3)3C-co-ch-ch=ch/TT) NaBH^ oh V /—v II n (ch3)3c-ch-ch-ch = ch-/ h > n I] ! v_y n [] Preferred compounds of formula (II) required as 1q starting materials in carrying out the process according to 1 2 the invention are those in which R , R and Y have those meanings which have already been mentioned for these substituents in connection with the description of the preferred and particularly preferred compounds according 15 to the invention.

The compounds of the formula (II) are known or can be prepared in a simple manner, according to processes which are known in principle (see 'United States P<Jt ent Specification 4*380,628 and the literature 2q quoted therein). Thus a compound of the formula (II) is obtained by reacting a keto-enam|;n^-^'^xthe general formula ^ Ire—-'A 21 3S3 202416 /R3 R1 - CO - C = CH - N (III) /Ns ^ R^ \\ V n ii 1 R and Y have the meaning given above and 3 4 R and R are identical or different and represent an alkyl radical having 1 to 4 carbon atoms, especially a methyl radical, with an organo-magnesium compound of the general formula in which Hal - Mg - R2 (IV) in which ? 1q R has the meaning given above and Hal represents a halogen atom, in the presence of an inert organic solvent (such as ether), and, if appropriate, in the presence of an inert gas (such as nitrogen), at a temperature between -20 and 120°C (in this context, see also (United States Patent Specification 4,380,628 ancj preparative Examples).

The keto-enamines of the formula (III) are known or can be prepared in a simple manner, according to processes which are known in principle (s-ee United States Patent Specification 4,380,628). Thus, a keto-amine of the formula (III) is obtained by reacting, at the boil, an azolyl-ketone of the general formula CO - CH2 /Y (V) in which R and Y have the meaning given above, with an amide acetal or aminal ester of the general formula Lm A 21 TfW. 202416 R5O yn \ / CH-N ^ ^4 R 0 R (Via) or NR3R4 R50-CH (VIb) ^ NR3R4 in which 3 4 R and R have the meaning given above, and R^ represents an alkyl radical having 1 to 4 5 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. Ber. 101, 41-50 (1968); J. Org. Chem. 43., 4,248-50 (1 978), and the preparative Examples). The azolyl-ketones of the formula (V) are known (see, for example, Great Britain Patent Specification 224 and Great Britain Patent Specification 15 l ,333^~706 ^nd New Zealand Patent Specification 1"81, 823); 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.

Jhe amide acetals or aminal esters of the formulae (Via) or (VIb) are generally known compounds of organic chemistry (see, for example, Chem. Ber. 101 , 41-50 (1968 ) and J. Org. Chem. 42, 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 (la) are organic sq.-Lv^qf-s^w.hich are inert ^ C%„ L—g*as£tes38a. ;;'v '(i 7' i • \ 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, 5 toluene or xylene), and halogenated hydrocarbons (such as methylene chloride, carbon tetrachloride, chloroform or chlorobenzene).

The process, according to the invention, for the preparation of the azolyl-alkenones of the formula (la) 10 is carried out, if appropriate, in the presence of a base as a catalyst. These include, as preferences, organic nitrogen bases, such as morpholine, pyridine, triethylamine and N,N-dimethylbenzylamine.

In the process, according to the invention, for 15 the preparation of the azolyl-alkenones of the formula (la) the reaction temperatures can be varied within a relatively wide range. In general, the reaction is carried out at a temperature between 30 and 150°C, preferably between 50 and 120°C.

The process, according to the invention, for the preparation of the azolyl-alkenones of the formula (la) is carried out either completely thermally, by heating the compounds of the formula (II), or as a base-catalysed reaction, 0.1 to 1 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 invention are isolated in a customary manner in all cases.

The reduction, according to the invention, for the preparation of the azoly1-alkenols of the formula (I) 30 is effected in a customary manner, for example by reacting the azolyl-alkenone of the formula (la) with a complex hydride, if appropriate in the presence of a diluent, or by reacting the azolyl-alkenone of the formula (la) with aluminium isopropylate in the presence of a diluent. 35 If complex hydrides are used, suitable diluents for this reaction according to the invention 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 5 reaction is carried out in general at a temperature from 0 to 3Q°C, preferably at from 0 to 20°C. For this purpose, about 1 reaction equivalent of a complex hydride (such as sodium borohydride or lithium alanate) is employed per mol of the ketone of the formula (la). To isolate 10 the reduced compounds of the 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 according to the invention are alcohols (such as isopropanol), or inert hydrocarbons (such as benzene). The reaction temperatures can again be varied within a relatively wide range; in general, the reaction is carried out at a temperature between 20 and 20 12Q°C, preferably at from 50 to 100°C. To carry out the reaction, about 1 to 2 mol of aluminium isopropylate are employed per mol of the ketone of the formula (la). To isolate the reduced compounds of the formula (I), the excess solvent is removed by distillation i_n 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.

Preferred acids for the preparation of acid addition salts 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 invention 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 20241 dissolving a compound of the formula (I) in a suitable inert solvent and adding the acid, for example hydrochloric acid, and can be isolated in a known manner, for example by filtration, and can be purified, if appropriate, 5 by washing with an inert organic solvent.

Preferred salts for the preparation of metal salt complexes 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 10 metal salt complexes according to the invention as being preferred.

The metal salt complexes of compounds of the formula (I) can be obtained in a simple manner according to customary processes, thus, for example, by dissolving the 15 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.

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 25 also exert several different 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 30 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. 35 Such inhibition of growth is inter alia of economic inter- 2 4 16 est in the case of grasses, 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 10 in 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 counteracts lodging. Use of growth regulators for shortening 15 and strengthening the stem enables higher amounts of fertiliser 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 20 that greater 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 lead to increases in yield, since the nutrients 25 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 30 utility if it is the vegetative parts of the plants which are harvested. Promoting the vegetative growth can, however, also simultaneously lead to a promotion of generative growth, since more assimilates are formed, so that more fruit, or larger fruit, is obtained. 35 Increases in yield can in some cases be achieved jti ^ ^ * ft 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 5 growth regulators. 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 or cereals. Using growth regulators it is also possible, for example, to inhibit the degradation 10 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 15 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 20 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 in the 25 cultivation of ornamental plants, also in connection with growth inhibition. On 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 cultivation of tobacco or in the planting of tomatoes. 30 The amount of leaf on plants can be controlled, under the influence of growth regulators, so that defoliation 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-35 tating harvesting in other crops, such as in viticulture.

L«g""/V,l2r1w*g»fc Defoliation of the plants can also be carried out to lower the 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. By alternance there is understood the peculiarity of some varieties of fruit to produce very different yields from year to year, for endogenic 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. ^5 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 it is thereby possible to achieve optimum adaptation to market requirements. 20 Furthermore, growth regulators can at times 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 25 mechanical or manual harvesting in only a single pass, for example in the case of tobacco, tomatoes or coffee.

Using growth regulators, 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 30 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 35 by late frosts. ^"7 7 Finally, the resistance of plants to frost, drought or a high salt content in the soil can be induced with growth regulators. Cultivation of plants in regions which are usually unsuitable for this purpose thereby becomes 5 possible.

The preferred time of application of the growth regulators depends on the climatic and vegetative circumstances.

The foregoing description should not be taken as implying that each of the compounds can exhibit all of the described effects on plants. The effect exhibited by a compound in any particular set of circumstances must be determined empirically.

The active compounds according to the invention 15 also exhibit a powerful microbicidal action and can be employed in practice for combating undesired microorganisms. The active compounds are suitable for use as plant protection agents.

Fungicidal agents in plant protection are employed 20 for combating Plasmodiophoromycetes, Oomycetes, Chytridio-mycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.

The good toleration, by plants, of the active compounds, at the concentrations required for combating plant 25 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 3Q good success for combating those fungi which cause powdery mildew diseases, thus, for combating Erysiphe species, such as, for example, against the powdery mildew of barley or of cereal causative organism (Erysiphe graminis), for combating stripe disease of barley (Drechsiera graminea), 35 for combating Venturia species, such as, for example, iA ,fl1i 305 20241 against the apple scab causative, organism (Venturia inaequalis), or for combating rice diseases, such as, for example, Pyricularia oryzae and Pellicularia sasakii.

The active compounds can be converted into the 5 customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine capsules in polymeric substances and in coating compositions for seed, as well as ULV formulations.

These formulations may be produced in known manner, -] 0 for example by mixing the active compounds with extenders, that 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 15 of water as an extender, organic solvents can, for example, also be used as auxiliary solvents.

As liquid diluents or carriers, especially solvents, there are suitable in the main, aromatic hydrocarbons, such as xylene, toluene or alkyl naphthalenes, 20 chlorinated aromatic or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, 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 25 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 gaseous diluents or carriers are meant 30 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 35 minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as highly-dispersed silicic acid, alumina and silicates. As solid carriers for granules there may be used crushed and fractionated 5 natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic 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-fatty acid -esters, polyoxyethylene-fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulphonates, 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 natural and synthetic polymers 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 oxide, titanium oxide and Prussian Blue, and organic dyestuffs, 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 zinc.

The formulations in general 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 active compounds, such as fungicides, insecticides, acaricides and herbicides, and also as mixtures with fertilisers and other growth regulators.

The active compounds can be used as such, in the 2024 form of their formulations or as the use forms prepared therefrom, such as ready-to-use solutions, emulsifiable concentrates, emulsions,foams, suspensions, wettable powders, pastes, soluble powders, dusting agents and 5 granules. They 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 10 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 amounts 15 applied can be varied within a relatively wide range.

In general, 0.01 to 50 kg, preferably 0.05 to 10 kg, are employed per hectare of soil surface.

When the substances according to the invention are employed as fungicides, also, the amount applied can 20 be varied within a relatively wide range, depending on the type of application.

Thus, especially in the treatment of parts of plants, the active compound concentrations in the use forms are in general between 1 and 0.0001% by weight 25 preferably between 0.5 and 0.001% by weight.

In the treatment of seed, amounts of active compound of 0.001 to 50 g per kg of seed, preferably 0.01 to 10 g, are generally required.

In the treatment of soil, active compound 30 concentrations of 0.00001 to 0.1% by weight, preferably 0.0001 to 0.02%, are generally required, at the place of action.

The present invention also provides plant growth regulating or fungicidal composition containing as active 35 ingredient a compound of the present invention in admixture .rfj ^ ) i. with a solid or liquefied gaseous diluent or carrier or in admixture with a liquid diluent or carrier containing a surface-active agent.

The present invention also provides a method of com-5 bating fungi which comprises applying to the fungi, 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 invention in admixture with a diluent or carrier.

The present invention also provides a method of regulating the growth of plants which comprises 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 15 invention in admixture with a diluent or carrier.

The present invention further provides crops protected from damage by fungi by being grown in areas in which immediately prior to and/or during the time of the growing a compound of the present invention was applied 20 alone or in admixture with a diluent or carrier.

The present 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 the growing a compound of the present invention was 25 applied alone or in admixture with a diluent or carrier.

It will be seen that the usual methods of providing a harvested crop may be improved by the present invention.

The Examples which follow illustrate the preparation of the substances according to the present invention. 30 Preparative Examples Example 1 (CH3)3C - CO - CH - CH = CH -(H) rA U) LWl ft 'S'l'VjQS 202416 g (0.073 mol) of 6-cyclohexyl-2,2-dimethyl-4-(1 , 2,4-1riazol-1 -y1)-hex-4-en-3-one and 200 g of aluminium oxide in 300 ml of methanol were heated under reflux for 24 hours. The reaction mixture was allowed to cool and was filtered under suction over kieselguhr, and the filtrate was concentrated. 19.9 g (99% of theory) of 6- cyclohexyl-2,2-dimethyl-4-(l,2,4-triazol-1-yl)-hex-5-en- 3-one of refractive index n^ = 1.4890 were obtained. Preparation of the starting material a) (CH3 ) 3C - CO - C = CH - CH2 H rf An N jj 44.4 g (0.2 mol) of 2,2-dimethyl-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 g (0.24 mol) of cyclohexylmethyl-magnesium bromide in 200 ml of ether was added at -20°C. 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 g (49.8% of theory) of 6-cyclohexyl-2,2-dimethyl-4-(1,2,4-triazol-1 - y1)-hex-4-en-3-one of refractive index = 1.4910 were obtained.

(CH3)-3-C - CO - C = CH - N(CH3)2 b) |f N N [J ' 250.8 g (1.5 mol) of 2 , 2-dimethy1-4-(1,2,4-triazol-25 1-yl)-butan-3-one were heated under reflux with 196 g (1.65 mol) of dimethylformamide dimethylacetal for 5 hours.

LA. ,2 1 .Jfl'T «- ■ ' <^'J Thereafter, the excess acetal was distilled, off. 306 g (92% of theory) of 2,2-dimethyl-5-dimethylamino-4-(1,2,4- 2 0 triazol-l-y1)-pent-4-en-3-one of refractive index nD = 1.531 were obtained.

/N (ck3)3c - co - ch2 - n c) Wn 138 g (2 mol) of 1,2,4-triazole were added in portions to 276.A g (2 mol) of ground potassium carbonate and 296.2 g (2 mol) of a-chloropinacolin in 500 ml of acetone at room temperature, the internal temperature 10 increasing to the boiling point. The mixture was stirred under reflux for 5 hours and was then cooled to room temperature. The reaction mixture was filtered, and the filtrate was concentrated by distilling off the solvent in vacuo. The oily residue crystallised after the addition 15 of naphtha. 240.8 g (72% of theory) of 2,2-dimethyl-4-(1,2,4-triazol-l-yl)-butan-3-one of melting point 62 to 64°C were obtained.

Example 2 oh (ch3)3c - ch - ch - ch = ch -/Ti~\ 1 \_y (?) fl ,Nr n ij 10.4 g (0.038 mol) of 6-cyclohexyl-2,2-dimethyl- 4-(1,2,4-triazol-l-yl)-hex-5-en-3-one (obtained as described in Example 1) were dissolved in 100 ml of methanol, and a solution of O.38 g (0.01 mol) of sodium borohydride in 5 ml of ice-water was added dropwise at -10°c. Stirring 25 was continued for a further 2 hours, and the reaction mixture was then adjusted to a pH value of from 6 to 7 with dilute hydrochloric acid. The reaction mixture was 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 6-cyclohexyl- 2,2-dimethyl-4-(1,2,4-triazol-l-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 Example No.

R- X - CH - CH = CH - R2 R (I) Melting point (°C), refract- • ^ 20 l.ve. index 3 (ch3 v^4 0 1 co n "c6h13 1.5388 4 (ch3 3C- co n ~c7h15 1. 4778 (ch5 3C" co n -c3h7 1. 4880 6 (ch3 3C" co n 105-108 7 8 9 11 12 13 (CH, (CH, (CH- (CH- (CH- (CH- (CH- ,C- ,C- ,C- ,C- -C- rC~ ,c- co CO CO GO CO CO CO N N N N N N N Hg>-Cl -i-C^Hy -CH2-i-C3H7 CI.

CI / -CH(C2H5)2 1.5512 1.4871 1.4868 1.5434 138-140 1.5624 1.4885 A—S Auui^uSJi '2024 Table 2 (continuation) Example , No. r: R Melting point (°C), refract- • ^ 20 i.ve .index, n^ . 14 cich2c(ch3)2- co n -CH2-i-.C3H7 1.4969 fch2c(ch3)9- co n -CH2-i-C3H7 1.4777 ci 16 (ch3)3c- ch(oh) n viscous oil 17 (ch3)3c- ch(oh) n -°3H7 1.4898 18 (ch3)3c- ch(oh) n "C6H13 1.4798 19 (ch3)3c- ch(oh) n -<g>"C1 1.5633 (ch3)3c- ch(oh) n -i-C3H7 1.4841 21 (ch3)3c- ch(oh) n -CH2-i-C3H7 1.4857 22 (ch3)3c- ch(oh) n -C7hi5 1.4807 23 (chx),c- ch(oh) n "C^P 112-124 24 (ch ) c- ch(oh) N -Crci 154-156 J J /ci (A form) (CH ) C- ch(oh) n -#-ci 46-48 J J ci (B form) 26 (ch^) c- ch(oh) n 180 (A form) ci 27 (ch3)3c- ch(oh) n -ch(c2h5)c4h9 1.4832 28 (ch3)3c- ch(oh) n -CH(C2H5)C4H9 1.4832 29 C1CH2C(CH3)2- ch(oh) n -CH2-i-CjHj 1.5001 FCH2C(CH3)2- ch(oh) n -CH2-i-C3H7 1.4852 31 Cl-<g>- ch(oh) n 50-60 32 (ch3)3c- co CH "C3H7 1.4915 i/ii ji j8a> Table 2 (continuation) Example , No. r1 x . .y. .. . r2.

Melting point (°c), refractive • 0 20 . index, rip. 33 (ch3 3c~ co ch "c6h13 1.4773 34 (ch3 3c~ co ch -c7hi3 1.4808 (ch3 3c" co ch -c8h17 1.4742 36 (CEj 1 O K~\ co ch "c9h19 1.4770 37 (oh3 3c" co ch -c5hh ci 1.4890 38 (ch3 3°- co ch 39 (ch3 3C" co ch -<£> 40 . (ch3 3°- co ch -c5hu ci X. 41 (ch3 3C" ch(oh) ch -<§bcl 42 (ch3 3C" ch(oh) ch -C6H13 43 (ch3 3C" ch(oh) ch <E> 44 Br-<f y co n © 45 Br-@- co n © viscous oil 1.5018 1.4892 92-96 1.4742 1.5050 46 46 c3h7-c(ch3)2- ch(oh) n -CH2-i-C3H7 107-111 (x CuClg) 1.4849 A form and B form = the two possible geometric isomers 47 48 ch30-<g>- (ch3)3c- ch(oh) co n n c2h5 -ch2-c(ch3)3 1.5320 (A form) 1.4828 49 (ch3)3c- co n -ch2^h> 1.4884 50 (ch3)3c- ch(oh) n -ch2-<h> 1.4887 51 52 (ch,),c-i-^Cl Cl-01 ch(oh) ch(oh) n n -ch2-c(ch3)3 -CH2-i-C3H7 62 49 53 CH3°~@~ ci^c1 ch(oh) n c2h5 40 (B form) 54 ch(oh) n C2H5 67 .a*, 385.

\ Table 2 Example No. [continuation) 55 56 57 58 c3h7~c(ch3)2 (ch3)3c- (ch3)3c- Cl^O-^- X Y CO N CO N CH(OH) N CO N" Melting point (°c), refractive r,2 . , 20 R index n^ ~CH2^3H7-i 1.4819 -ch2-ch(ch3)-c2h5 1 . 477 2 -ch2-ch (ch3) -c2h5 1 • 4 81 9 ch. 1 . 5996 The plant growth regulating and fungicidal 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 corresponding preparative Example.

The known comparison compounds are identified as follows: (A) (B) oh (ch3)3c-i!:h-ch-ch=c' rH oh (ch3)3c-ch-ch-ch^ ff^N n y ch3 ch3 oh I (c) = (ch3)3c-c c h-c h = c ■Vk, fi n j u \ ch3 ch3 (D) oh (ch3)3c-ch-(j:h-ch=q> fl N n li x h2 soif (E) (ch3)3c-co-ch-ch: n a ch3 ■IxUto—J>i' 1 "Si" 305- 202 - 30.- Example A Inhibition of growth' of 'soy'a "beans Solvent: 30 parts by weight of dimethylformamide Emulsifier: 1 part by weight of polyoxyethylene sorbitane 5 monolaurate To produce a suitable preparation of active compound, 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. ^ 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% 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 (21) and (19) according to the invention showed a better inhibition of growth than the compound (A) 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 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.

Grass (Festuca pratensis) was grown in a greenhouse up to a height in growth of 5 cm. In this stage, 35 the plants were sprayed with the preparations of active ^ ' ■: • , •* - j /> ■V-.2? 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 5 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 10 from the prior art.

Example C Influence on growth of sugar beet Solvent: 30 parts by weight of dimethyIformamide Emulsifier: 1 part by weight of polyoxyethylene sorbitane 15 monolaurate To produce a suitable preparation of active compound, 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 20 water.

Sugar beet was grown in a greenhouse until formation of the cotyledons was complete._ In this stage, the plants were sprayed with the preparation of active compound until dripping wet. After 14 days, the additional 25 growth of the plants was measured and the influence on growth in per cent of the additional growth of the control plants was calculated. 0% influence on growth denoted a growth which corresponded to that of the control plants. Negative values characterised an inhibition of 30 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), (18), (19), (21), (26), (36) and (41) according to the invention had 35 a greater influence on growth than the compounds (C) and (D) °1 gfifr 2024 16 known from the prior art.

Example D Inhibition of growth of cotton Solvent: 30 parts by weight of dimethyIformamide 5 Emulsifier: 1 part by weight of polyoxyethylene sorbitane monolaurate To produce a suitable preparation of active compound, 1 part by weight of active compound was mixed with the stated amounts of solvent and emulsifier and the 10 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-15 ive compound until dripping wet. After 3 weeks, the additional growth of the plants was measured and the inhibition of growth in per cent of the additional growth of the control was calculated. 1001 inhibition of growth meant that growth had stopped and 0% denoted a growth 20 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 from the prior art.

Example E Stimulation of the fixation of CO^ in soya beans Solvent: 30 parts by weight of dimethylfo.rmamide 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 made up to the desired concentration with water.

Soya bean plants were grown in a greenhouse until LjC""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 CO2 in the 5 plants was determined by customary methods. The values were compared with those of the control plants which had not been treated with the active compounds.

The figures of merit had the following meanings: - denoted inhibition of the fixation of CC>2 10 0 denoted fixation of CC^ as in the case of the control + denoted low stimulation of the fixation of CO^ + + denoted powerful stimulation of the fixation of CC>2 +++ denoted very powerful stimulation of the fixation of C02 In this test, the active compounds (1) and (22) according to the invention showed stimulation of the fixation of C02, in contrast to the compounds (A), (B) and (E) known from the prior art.

Example F Erysiphe test (barley)/protective Solvent: 100 parts by weight of dimethyIformamide 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 concentration .

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-35 ature of about 20°C and a relative 'atmospheric humidity of LP A 31 J8: ' 1 1 iJ J / > ~ -d, -cv about 80%, in order to promote the. development, of powdery mildew pustules.

Evaluation was carried out 7 days after the inoculation.

In this test, a clearly superior activity com- ■ pared with the compound (E) known from the prior art was shown, for example,, by the compounds (5) s (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 active compounds were used as dry dressings.

These were prepared by extending the particular active com-15 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. 20 The seed was embedded in sieved, moist standard soil and was exposed to a temperature of 40°C 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 25 pregerminated barley were subsequently sown 3 cm deep in standard soil and were cultivated in a greenhouse at a temperature of about l8°C in seedboxes which were exposed to light for 15 hours daily.

About 3 weeks after sowing, the plants were evaluated 30 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). 202416

Claims (1)

1. WHAT WE CLAIM IS: 1. Compounds which are azolyl-alkenones and -ols of the general formula R1 - X - CH - CH = CH - R2 I (!) rfN y N 11 5 in which R^" represents an alkyl, halogenoalkyl or optionally substituted phenyl radical, 2 . R represents an alkyl, optionally substituted phenyl, optionally substituted cyclcalkyl or 10 optionally substituted cycloalkylalky1 radical, X represents a CO or CH(OH) group, and Y represents a nitrogen atom or a CK group, and the acid addition salts and metal salt complexes thereof. 15 2. Compounds according to claim 1, in which R^" represents a grouping of the general formula ^/ch2Z1 -C-CH, \ 2 XCH2Z^ 1 2 Z and Z are identical or different and represent 20 a hydrogen or halogen atom or an alkyl radical having 1 to 4 carbon atoms, or R^" represents a phenyl radical which can be mono-substituted or polysubstituted by identical or different substituent(s) selected from halogen, alkyl 25 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 30 atoms and 1 to 5 identical or different halogen 202416 - 36 - 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, 2 5 R represents a straight-chain or branched alkyl radical having 1 to 12 carbon atoms, . or a phenyl radical which can be monosubstituted or polysubstituted by identical or different substituents selected from halogen, alkyl having 1 to 4 10 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 15 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 20 R 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 cycloalkylalky1 radical which has 3 to 7 carbon atoms in the cycloalkyl part and 1 or 2 car— 25 bon atoms in the alkyl part and is optionally sub stituted by halogen and/or alkyl having 1 to 4 carbon at oms , X represents a CO or CH(OH) group, and Y represents a nitrogen atom or a CH group. 30 3. Compounds according to claim 1, in which R^ represents a grouping of the general formula /CH2Z1 -C-CH, , V3Z2 lit A 01 305- 202416 - 37 - 12 . Z and Z are identical or. different and represent a hydrogen, fluorine, chlorine or bromine atom or a methyl, ethyl, propyl or butyl; or R represents a phenyl radical which is optionally 5 monosubstituted to trisubstituted by identical or different substituents selected from fluorine, chlorine, methyl, isopropyl, tert.-butyl, methoxy, methylthio, isopropoxy, trifluoromethy1, trifluoro-methoxy, trifluoromethylthio, methylamino, dimethyl-10 amino, and phenoxy or phenyl optionally substituted by fluorine, chlorine or methyl; 2 R represents a straight-chain or branched alkyl radical having 1 to 8 carbon atoms, or a phenyl radical which is optionally monosubstituted to trisubstituted 15 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 20 optionally substituted by fluorine, chlorine or methyl; 2 of R represents a cyclopropyl, cyclo- butyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethy1, cyclopentylmethyl or cyclohexyl-25 methyl radical, each of which is optionally substi tuted by methyl, ethyl, isopropyl, fluorine or chlorine; X represents a CO or CH(OH) group and Y represents a nit.rogen atom or the CH group. 30 4. Any one of those compounds according to claim 1 which are hereinbefore specifically identified. 5. A process for the production of a compound according to any of claims 1 to 4, characterised in that a compound JL»i A 01 JOT t. „x ^ ' I • ; -c; .-•>-) \ 202416 " 38 - of the general i ormuia R1 - CO - C = CH - CH2 - R2 | 2 (II) N i| in which 1 2 R , R 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 R1 - CO - CH- CH = CH - R2 I (la) c in which 12 ... R , R and Y have the same meanings as m claim 1, is reduced;and, if desired, an acid or a metal salt is then added onto the compound according to claim 1 produced by the foregoing process. ^6. A process according to claim 5, in which the com pound of formula (II) is heated in the presence of a catalyst or in the presence of aluminium oxide. 7. A process according to claim 6, in which the catalyst is an organic nitrogen base. ?0 one 8. A process according to any/of claims 5 to 7, in which the compound of formula (II) is heated in the presence of an inert organic solvent, as diluent. 9. A process according to any^f claims 5 to 8, in which the compound of formula (II) is heated at a temper-ature between 30 and 150°C. one 10. A process according to any/of claims 5 to 9, in which the compound of formula (la) is reduced by reaction with a complex hydride or aluminium isopropylate, in the presence of a diluent. Lm A Q1 505 fa-)FE3!?S5 V,.. - 39 - 11. A process for the preparation of a compound according to claim 1, substantially as described in any^of Examples 1 to 54. 12. A compound according to claim 1, characterised in 5 that it is prepared by a process according to any^cff claims 5 to 11. 13. A plant-growth-regulating or fungicidal composition, characterised in that it contains as active ingredient a compound according to any of claims 1 to 4 and 12 in 10 admixture with a solid or liquefied gaseous diluent or carrier or in admixture with a liquid diluent or carrier containing a surface-active agent. 14. A composition according to claim 13, characterised in that it contains from 0.1 to 95$ of the active compound, 15 by weight. of . . 15. A method/combating fungi, characterised m that there is applied to the fungi, or to a habitat thereof, a compound according to any of claims 1 to 4 and 12 alone or in the form of a composition containing as active 20 ingredient, a compound according to any of claims 1 to 4 and 12, in admixture with a diluent or carrier. 16. A method according to claim 15, characterised in that a composition is used containing from 1 to 0.0001% of the active compound, by weight. 25 17• A method according to claim 16, characterised in that a composition is used containing from 0.5 to 0.001% of the active compound, by weight. IS. A method according to claim 15, characterised in that the active compound is applied to soil in the form of a composition, said composition containing from 0.00001 to 0.1% of the active compound by weight. 19. A method according to claim 18, characterised in that the composition contains from 0.0001 to 0.02% by weight. 20. A method according to claim 15, characterised in that the active compound is applied to seed in an amount of a 20241G - no - O.OOl to 50 g per kg of seed. 21. A method according to claim 20, characterised in that the active compound is applied to seed in an amount of 0.01 to 10 g per kg of seed. 5 22. A method of regulating the growth of plants, characterised in that there is applied to the plants, or to a habitat thereof, a compound according to any of claims 1 to 4 and 12 alone or in the form of a composition containing as active ingredient a compound according to 10 any of claims 1 to 4 and 12, in admixture with a diluent or carrier. 23. A method according to claim 22, characterised in that the active compound is applied to an area of agriculture in an amount of 0.01 to 50 kg per hectare. 15 24. A method according to claim 23, characterised in that the active compound is applied to an area of agriculture in an amount of 0.05 to 10 kg per hectare. BAYER AKTIENGESELLSCHAFT By Their Attorneys HENRY HUGHES LIMITED