CA1169075A - Substituted l-phenyl-2-triazolyl-pent-l-en-3-ols, a process for their preparation and their use as plant growth regulators and fungicides - Google Patents

Abstract

ABSTRACT OF THE DISCLOSURE
Substituted 1-phenyl-2-triazolyl-pent-1-en-3-ols of the formula (I), in which X represents a halogenoalkyl, halogenoalkoxy, halogenoalkylthio, alkylthio, nitro, hydroxyl, dialkylamino, alkylcarbonyloxy or optionally substituted benzyloxy radical, Y represents a halogen atom, an alkyl, alkoxy or cyano radical or an optionally substituted phenyl or phenoxy radical, m is 1, 2 or 3 and n is 0, 1, 2, 3 or 4, with m and n together be-ing at most 5, or their acid addition salts and metal salt complexes, a process for their preparation and the use of the novel compounds as plant growth regulators and fungicides.

1-Phenyl-2-triazolyl-pent-1-en-3-ones of the formula

Description

The present invention relates to certain new substituted l-phenyl--2-triazolyl-pent-l-en-3-ols, to a process for their production, and to their use as plant growth regulators and Eungicides.
It has already been disclosed that certain 4,4-dimethyl-1-phenyl-2-triazolyl-pent-l-en-3-ols possess a good fungicidal activity (see DE-OS

2,838,847). The action of these compounds is however not always fully satis-factory, especially if low amounts and low concentrations are used. The plant growth-regulating action of these azole derivatives is also not always entirely satisfactory.
According to the present invention we provide, as new compounds, the substituted l-phenyl-2-triazolyl-pent-1-en-3-ols of the general formula OH

y ~ c )) C~l - C(C33)3 (I~

N
in which X represents a halogenoalkyl, halogenoalkoxy, halogenalkylthio, alkylthio, nitro, hydroxyl, dialkylamino or alkylcarbonyloxy radical, or re-presents a benzyloxy radical optionally substituted in the phenyl moiety by substituents selected from fluorine, chlorine, bromine and alkyl, Y represents a halogen atom, an alkyl, alkoxy or cyano radical or a phenyl or pheno~y radical optionally substituted by substituents selected from fluorine, chlorine, bromine and alkyl, _ is ], 2 or 3, n is 0, 1, 2, 3 or 4, and m ~ n = 1 to 5, ~ or a non~phytotoxic acid addition salt or metal salt complex thereof wherein :

'~ ~

.
, .: " '~ . : ' ' ' 1 ~9075 the metal is selected from those of ma~n groups II to IV and oE sub-groups I, II and IV to VIII of the periodic table.
One embodiment of the invention relates to the compounds of formula (I) in which X represents a halogenoalkoxy, halogenalkylthio, alkylthio, hydroxyl, dialkylamino or alkylcarbonyloxy radical, or represents a oenzyloxy radical optionally substituted in the phenyl moiety by substituents selected from fluorine, chlorine, bromine and alkyl, and Y, m and n are as defined above, and the other embodiments of the invention re:lates to thQ compound$ of formula (I) in which X represents a halogenoalkyl or nitro group, and Y, _ and n are as defined above.
The compounds according to the present invention, of the formula (I), occur as the geometrical E (trans) and Z (cis) isomers.
In the E,Z nomenclature, the substituents present on the double bond are classified according to the Cahn-Ingold-Prelog Rule in accordance with decreasing priority. If the preferred substituents are on the same side of the double bond, the compound is in the Z configuration (derived from the German word zusammen, that is to say together), whilst if they are on opposite sides, the compound is in the E configuration (derived from the German word entgegen, that is to say opposed).
; 20 Since, furthermore, an asymmetric carbon atom is present, the -~ compounds of the formula (I) can occur in two optical isomer forms~
The present invention relates both to the individual isomers and to the isomer mixtures.
According to the present invention we further provide a process for the production of a compound of the present invention characterized in that a l-phenyl-2-triazolyl-pent-1-en-3-one of the general formula ~:~
"
: ' ' .

~ ~6~07~

, ~ ~ CH = C - C0 - C(CH3)3 (II) : n ~ N~N

N
in which X, Y, n and m have the abovementioned meanings, is reduced, and the resulting compound of the formula (I) is, if desired, subsequently subjected to an addition reaction with an acid or with a metal salt.
Finally, it has been found that the compounds of the present invention which are substituted l~pheny1~2-triazolyl-pent-1-en-3-ols of the formula (I) as well as their addition salts with acids and their metal-salt complexes, exhibit powerful plant growth-regulating properties and powerful fungicidal properties, accordingly we still further provide a compound as defined above, in which X represents a 2-, 3- or 4- trifluoromethyl radical or a 3- or 4- nitro radical, Y represents a 2-, 3- or 4- chlorine atom, _ is 1 and n is 0 or 1.
Surprisingly, the compounds according to the invention exhibit a better plant growth-regulating action and fungicidal action than the 4?4~
dimethyl-l-phenyl-2-triazolyl-pent-1-en~3-ols known from the state of the ar~, which are closely related compounds both chemically and in respect of their : action~ The active compounds according to the invention thus represent an enrichment o~ the art.
Preferred substituted l-phenyl-2-triazolyl~pent~l-en=3-ols of ~` formula (L) according to the present invention are those in which X represents a halogenoalkoxy or halogenoalkylthio radical, each with 1 to 2 carbon atoms and up to 5 identical or different halogen atoms (such as, : in particular, fluorine and chlorine atoms), an alkylthio radical with 1 to 4 ~:
~ -3-. . . . .

~ ~ .
. ;: ' ~;

1 ~6907~

carbon atoms, hydroxyl radica], a dialkylamino radical with 1 to 4 carbon atoms in each alkyl part, an alkylcarbonyloxy radical with 1 to 4 carbon atoms in the alkyl part or a benzyloxy radical which is optionally substituted in the phenyl part (preferred substituent(s) being selected Prom fluorine, chlorine, bromine and alkyl with 1 or 2 carbon atoms), Y represents a fluorine, chlorine or bromine atom, an alkyl or alkoxy radical, each with 1 to 4 carbon atoms, a cyano radical or an optionally substituted phenyl or phenoxy radical preferred substituent(s) being selected from fluorine, chlorine, bromine and alkyl with 1 or 2 carbon atoms), _ is 1 or 2 and n is 0, 1, 2 or 3, or those in which X represents a halogenoalkyl radical with 1 to 2 carbon atoms and up to 5 identical or different halogen atoms (such as in particular fluorine andchlorine atoms) or a nitro radical and Y, m and n are as described just above.
Particularly preferred compounds of the formula (I) according to the present invention are those in which X represents a trifluoromethoxy or tri-: fluoromethylthio radical, a 1,1,2-trifluoro-2-chloro-ethoxy or -ethylthio radical, a methylthio, hydroxyl, dimethylamino, acetoxy or tert.-butylcarbony-loxy radical or a benzyloxy radical which optionally has one or two identical or different substituents selected from fluorine, chlorine and methyl, Y represents a fluorine or chlorine atom or a methyl, ethyl, iso-propyl, tert.-butyl, methcxy, isopropoxy or c~ano radical, or a phenyl or phenoxy radical which optionally has one or two identical or different sub-stituents selected from fluorine, chlorine and methyl, m is 1 or 2 and n is 0, 1 or 2, or those in which ~ represents a trifluoromethyl, difluorochloromethyl, fluorodichloro-methyl, trichloromethyl, 1,1,2-trifluoro-2-chloro-ethyl radical or a nitro :' :

1 ~9Q7~

radical, and Y~ _ and n h&ve the meaning mentioned ~ust above~
when, for example, 4,4-dimethyl-2-(1,2,4-triazol-l~yl)-1~(4, trifluoromethylphenyl)-pent-l-en-3-one and sodium borohydride are used as starting compounds, the course of the process according to the present inven-tion is illustrated b~ the following equation:
OH

3 ~ - I CO C(CH3)3 NaBH~ F3C ~ CH C - CH - C(CH3)3 E/Z isomer mixture E/Z isomer mixture when, for example, 4,4-dimethyl-2-(1,2,4-triazol~ 1)-1-(2-trifluoromethylphenyl)-pent-l-en-3-one and aluminium isopropylate are used as starting compounds, the course of the process according to the invention is illustrated by the :Eollowing equation:

~ CH C - CO - C(C33)3 Al(OC3 7-i~3 ~ 3 ~

E/Z isomer mixture Z isomer Preferred l-phenyl-2-triazolyl-pent-1-en-3-ones of formula (II) re-quired as starting compounds in carrying out the reduction according to the învention are those in which X, Y, m and n have the meanings already mentioned respectively in connection with the description of the preferred and parti-cularly preferred compounds according to the invention, of the formula (I).

The l-phenyl-2-triazolyl-pent-1-en-3-ones on the formula (II) have not previously been disclosed~
According to the present invention we therefore further provide, as new compolmds, the l-phenyl-2-triazolyl-pent-l~en~3-ones of the formula (II), ,~ J
~,.

`

,`

:, ' 7 ~
s defined above.
l-PheDyl-2-triazolyl-pent-1-en-3-ones of the present invention may be prepared by reacting a triazolyl-pinacoline of the formula H2C - CO - C(CH3)3 ~ N~ (III) with an aldehyde of the general formula m ~ ~ _ CH = O (IV) Yn ~, ~:`

~ ~5a~

..
i:: J
' :~

~ 169~75 in which X, Y, _ and n have the abovementioned meanings, in the presence of a solvent and in the presence of a catalyst.
The solvents which can be used for the preparation of the l-phenyl-2-triazolyl-pent-l-en-3-ones of the formula (II) are preferably inert organic solvents.
These preferably include alcohols (such as methanol and ethanol), ethers (such as tetrahydrofuran and dioxane), aliphatic and cycloaliphatic hydrocarbons (such as hexane and cyclohe~ane), aromatic hydrocarbons (such as benzene, toluene and cumene) and halogenated aliphatic and aromatic hydrocarbons (such as methylene chloride, carbon tetrachloride, chloroform, chlorobenzene and dichloro-benzene).
The preparation of the compounds of the formula(II) is carried out in the presence of a catalyst. Any of the acidic and, in particular, basic catalysts which a~e conventionally usable, as well as their buffer mixtures, can be employed. They preferentially include Lewis acids (such as boron trifluoride, boron trichloride, tin tetrachloride or titanium tetrachloride), organic bases (such as pyridine, 2,6-dimethylmorpholine and piperidine) and, in particular, piperidine acetate~
In carrying out this process, the reaction tempera-tures can be varied within a substantial range, In ; general, the reaction is carried out at a temperature between 20 and 160C, preferably at the boiling point of the particular solvent.
3 In carrying out this process, 1 to 1.5 mol of aldehyde of the formula (I~) and catalytic to 0.2 r-lar ,, ~
amounts of catalyst are employed per mol of tria~olyl-pinacoline of the formula (III). The products of the formula (II) are preferably obtained as E/Z isomer mixtures.
~eparation into the pure isomers is possible in a Le A 2 641 ` . ~

. ;~. .
`~' ' ' ' '' ' ~: ,....... . .

conventional manner, for example by crystallisation or by chromatographic separation processes.
The l-phenyl-2-triazolyl-pent-1-en-3-ones of the formula (II) are generally interesting intermediate pro-ducts for example for the preparation of the compoundsaccording to the invention~ of the formula (I)~ Used in appropriate concentrations, they also exhibit growth-regulating and fungicidal properties.
The reduction o~ the ketones of formula (II) according to the invention for the production of compounds of formula (I) is carried out in the usual manner, for example by reaction with complex hydrides, if appropriate in the presence of a diluent~ or by reaction with aluminium isopropylate in the presence of a diluent. ~he starting compounds of the formula (II) can be employed in the reduction as the E/Z isomer mixture or as pure isomers.
If co~plex hydrides are used, suitable diluents for the reaction according to the invention are polar organic solvents. These preferentially include alcohols (such as methanol, ethanol, butanol and isopropanol) and ethers (such as diethyl ether or tetrahydrofuran). The reaction is in general carried out at a temperature between -10 and +30C, preferably at a temperature between -lO
; and 20C. For this purpose, about 1 mol of a complex hydride (such as sodium borohydride, calcium borohydride or lithium alanate) is employed per mol of the ~etone of the formula (II). The isolation of the compound accord-ing to the invention is carried out in a conventional manner, as is any separation of the E/Z isomer mixtures which are always formed on reduction with complex hydrides if E/Z
isomer mixtures are used as starting materials of the formula (II).
If aluminium isopropylate is used, preferred suitable diluents for the reaction according to the invent-ion are alcohols (such as isopropanol) or inert hydro-Le A 20 641 ,i carbons (such as benzene). The reaction temperatures can, once again, be varied within a substantial range;
in general, t~e reaction is carried out at a temperature between 2C and 120C, preferably at a temperature between 50 and 100C. ~o carry out the reaction, about 1 to 2 mol of aluminium isopropylate are employed per mol of the correspcnding ketone of the formula (II). The compounds according to the invention are isolated in a conventional manner.
On reduction with aluminium isopropylate, exclu-sively the Z-isomers are obtained.
An unambiguous characterising feature of the two geometrical isomers is the Hl nuclear resonance of the two triazole protons. The difference in the shift values for these two protons is about twice as great in the E forms as in the corresponding Z forms.
Preferably, the following acids can be used for the preparation of addition salts of the compounds ~ the formula (I) with acids: the hydrogen halide acids (such as hydrobromic acid, and, especially, hydrochloric acid), phosphoric acid, nitric acid, sulphuric acid, monofunction-al and bifunctional carboxylic acids and hydroxycarboxylic 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 1,5-naphthalenedisulphonic acid).
The addition salts of the compounds of the formula (I) wi~h acids can be obtained in a simple manner by 3 conventional salt-forming methods, for example by dissolv-~`~ ing a compound of the formula (I) ln a suitable inert solvent and adding the acid, for exam~le hydrochloric acid, and can be isolated in a conventional manner, for example by filtering off, and be purifled, if appropriate, by washing with an inert organic solvent.

Le A 20 6~1.
.;

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Preferably, salts of metals of main groups II to I~, and of sub-group I and II, as well as I~ to VIII, are used to prepare the complexes of the compounds of the formula (I) with metal salts, examples to be mentioned being copper, zinc, manganese, magnesium, tin, ircn and nickel.
Suitable anions of the salts are preferably derived from the following acids: hydrogen halide acids (such as hydrochloric acid and hydrobromic acid), phosphoric acid and sulphuric acid.
The metal complexes of compounds of the formula (I) can be obtained in a simple manner by conventional processes, for example by dissolving the metal salt ir.
alcohol, for example ethanol, and adding the solution to the compound of the formula (I). ~etal salt complexes can be purified in a known manner, for example by filtering off, isolating and, where appropriate, recrystallising.
The substances which can be used 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 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 the way in which the compounds are appli~d. In ~very case, growth regulators are intended to influence the crop plants in the particular manner desired.
Plant growth regulating compounds can b~ employe~, for example, to inhibit vegetative growth of the plants.
~ Such inhibition of growth is inter alia of economic inter-; est in the case of grasses~ since it is thereby possible ~ 35 to reduce the frequency of cutting the grass in ornamental .
e A 20-641 --90 7 ~

- lC -gardens, parks and sportsgrounds, ~t verges, at airports or in fruit orchards. The inhibition of gro~th of herbacecus and wocdy 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 undesired, is also of importance.
The use of growth regulators to inhibit the growth in length of cereals is also important. The danger of lodging of the plants before harvesking 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 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 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 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, however, also simultaneously lead to a promotion of generative growth, since more assimilates are formed, so that more fruit, or larger fruit, is obtained.
Increases in yield can in some cases be achieved by affecting the plant metabolism, without noticeable changes in vegetative growth. A change in the composi-Le A 20 641 :

0 7 ~

tion of plants, which in turn can lead to a better qualityof the harvested products, can furthermore be achieved with 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 of desired constituents, such as, for example, sugar in sugar beet or sugar cane, before or after harvesting. It is also possible favourably to influence the production or the efflux of secondary plant constituents. ~he 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 import-ance 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 cultivation of ornamental plants, also in connection with growth inhibition. ~n 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.
- The amow~ of leaf on plants can be controlled, under the influence of growth regulatorsg so that defolia-tion of the plants at a desired point in time is achieved.
Such defoliation is of great importance in the ~echanical harvesting of cotton, but is also of interest for facili-tating harvesting in other crops, such as, for example, in vitlculture. De~oliation of the plants can also be carried out to lower the transpiration of plants before Le A 20-641 9~75 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. ~owever, 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 alter-nance 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 for~e 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 it is thereby possible to achieve optimum adaptation to market requirements.
Furthermore, growth regulators can at times improve the coloration of fruit. In addition, concentrating the the ripening within a certain period of time is also achievable with the aid of growth regulators. This provides the ~reconditions for being able to carry out complete mechanical or manual harvesting in only a single pass, for example in the case of tohacco, 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 pineapple or ornamental plants in nurseries, germinate, shoot or blossom at a time at which they normally shown no readiness to do cO
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 ~ 20 641 .
' .

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I ~L69075 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 beco~es possible.
The preferred time of application of the growth regula~ors depends on the clim2tic 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. ~he effect exhibited by a compound in any particular set of circum-stances must be deterr.~ined er.pirically.
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 er.~ployed for combating Plasmodiophoromycetes, Oomycetes, Chytridio-mycetes, Zygomycetes, Ascomycetes, Basidio~ycetes and Deuteromycetes.
The good toleration, by plants, of the active compounds, 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 against the powdery mildew of barley or cereal causative organism (Erysiphe graminis)j or for combating Venturia speciesj such as against the apple scab causative organism (Fusicladium dendriticum).

Le ~ 20 641 ' .

.

~ ~91)75 It should be emphGsised that the substances according to the in~ention not only display a protective action but in some cases also have a systemic action.
Thus, it is possible to prctect plants from furgal attack if the active compounds are fed to the above-ground parts of the plant via the soil and the root or via the seed.
The acti~Je compounds can be converted to the customary formulations, such as solutions, emulsions~ sus-pensions, powders, foams, pastes, granules, aerosols, very fine capsules in polymeric substances and in coating compositions for seed, as well as ULV formulations.
These formul2tions may be produced in known manner, for example by mixing the active compounds with e~tenders, 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 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 hydro-carbons, such as xylene, toluene or alkyl naphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic or alicyclic hydrocarbons, such as cyclohexane 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 cyclohexancne, or strongly polar solvents, such as dimethylformamide and dimethylsulphoxide, as well as watt~r.
By liquefied gaseous 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, Le ~ 20 641 --;: : ' .

~ 75 nitrogen ar.d carbon clioxide.
As solid carriers there may be used ground natural minerals, such as kaolins, clays, talc, chal~, 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 natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic lC 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 be used non-ionic and anionic emulsifiers, such as polyoxyethylene-fatty acid esters, polyoxyethylene-fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulphonates, alkyl sulphates, aryl sulphon-ates as well as albumin hydrolysis products. Dispersing agents include, for example, lignin sulphite waste liquors and methylcellulose.
Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, can be used in the formul-ations.
It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as ali~arin dyestuffs, azo dyestuffs or metal phthalocyanine dye-stuffs, 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 activ~ 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 `
Le A 20 641 ..
, , j .

~ 169075 other known active compounds, such as fungicides~ insec-ticides, acaricides and herbicides, and as mixtures with fertilisers and other growth regulators.
The active compcunds can be used as such or in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, emulsifiable concentrates, emulsions, foams, suspensions, wettable powders, pastes 3 soluble powders, dusting agents and granules. They are used in the customary manner, for example by watering, spraying, atomising, scattering, dusting, foaming, brushing and so on. It is further-ore possible to apply the active compounds by the ultra-low volume process or to inject the active compound itself into the soil. The seeds of the plants can also be treated.
When the compounds according to the invention are used as plant growth regulators, the amounts used can be varied within a substantial range. In general, 0.01 to 50 kg, preferably 0.05 to 10 kg, are used per hectare of soil surface.
When using the compounds according to the invention as fungicides, the amount used can again be varied within a substantial range, depending on the type of application.
Thus, for example, the active compound concentrations in the use forms, especially for the treatment of parts of plants, are in general between 1 and 0~0001% by weight, --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 3 generally required. In the treatment of soil, active compound concentrations of 0.00001 to 0.1% by w~ight, preferably of 0.0001 to 0 02%, at the action site are required.
The present invention also provides plant growth regulation or fungicidal composition containing as active " Le A 20 641 .

~ ~6~7 ingredient a compound cf the present invention in admixture 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 combating fungi which comprises applying to the fungi, or to a habikat 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 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 co~pound of the present invention was applied 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 applied alone or in admixture with a diluent or carrier.
3 It will be seen that the usual methods of providing a harvested crop may be improved by the present invention.
Preparative Examples Example l , Le A 20 641 ~ .

.

1 1~907 __~CF3 OH
- CH = C - CH - C(CH3 )3 N N (1) - Z isomer F

CH = C - CO - C(CH3 )3 N (II-E isomer 44.1 g (0.1365 mol) of 4,4-dimethyl-2-(1,2,4-triazol-l-yl)-1-(2-trifluoromethylphenyl)-pent-1-en-3-one, as an E/Z isomer mixture, and 27.9 g (Q.1365 mol) of aluminium isopropylate were heated for 7 hours in 350 ml of boiling isopropanol; at the same time, isopropanol and acetone were continuously distilled off through a 30 cm Vigreux column, until acetone was no longer detect-~' able in the distillate. The solution was then decomposed with ice/hydrochloric acid. After extraction withmethylene chloride, the organic phase was dried over sodium sulphate, filtered and evaporated in vacuo. The semi-crystalline mass which remained was chromatographed over silica gel 60 (Merck)/chloroform. mhe first fractions gave afker evaporating off the solvent~ 10.8 g (24% of theory) of E isomer of 4,4-dimethyl-2-(1,2,4-triazol-1-yl)-1-(2-trifluoromethylphenyl)-pent-l-en-3-one~ of melting point 82C.
The next fractions gave, after evaporating off the solvent, 12.8 g (28% of theory) of Z isomer of 4~4-~ dimethyl-2-(1,2,4-triazol-1-yl)-1-(2-trifluoromethy'-'` ~ phenyl)-pent~l-en-3-ol, of meltir.g point 136~C.
P'repar'at'i'on 'of'th'e st'ar't`i'ng product (a compound of formula (II)) .
I ' Le' A' 2'0''641 !~ `~ .

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1 ~9~7~

- CH = C - CO - C(CH3)3 (II-2) N~N
N ~ E/Z isomer mixture 25.2 g (0.15 mol) of 3,3-dimethyl-1-(1,2,4-triazol-1-yl)-butan-2-one and 26.1 g ~0.15 mol) of 2--trifluorobenzaldehyde in 350 ml of toluene were lleated under reflux wi-th 9 g of acetic acid and 3.6 ml of dimethylmorpholine for 20 hours, th~ water of reaction being removed azeotropically. The toluene solu-tion was washed with water, dried over sodium sulphate, filtered and evaporated ~n vacuo. 44.9 g (93% of theory) of 4,4-dimethyl-2-(1,2,4-triazol-1-yl)-1--(2-trifluoromethylphenyl)-pent-1-en-3-one were obtained as an E/Z isomer mix-ture, of a refractive index nD = 1.5113.
Example 2 CF OH

- CH = C - CH - C(CH3)3 ~N (2) E isomer A solution of 0.85 g (0.0242 mol) of sodium ~oranate in 20 ml of water was added dropwise to 10.7 g (0.0345 mDl) of the E isomer of 4,4-dimethyl-2--(1,2,4-triazol-1-yl)-1-(2-trifluoromethylphenyl)-pent-1-en-3-one (compare Example 1) and 2.45 g (0.0233 mol) of calcium chloride in 150 ml of isopropaniol at -5C.
After 18 hours, 20 ml of acetone were adided dropwise. After ev~porat-ing off the solvent, thie residue which remained was stirred into water and the mixture was extracted with methylene chloride. m e organic phase was separated off, dried o~er sodiiumisulphate, filtered and evaporated in vacuo. me crystal-line mass was stirred wi~hi diisopropyl ether and filtered off. 7.2 g (66.7~ of theory) ~' : ::

1 ~907~

of the E isomer of 4,4-dimethyl-2-(1~2,4-triazol-1-yl)-1-(2-trifluoromethylphenyl)-pent-1-en-3-ol, of melting point 165C, were obtained.
Example 3 pH
F3C ~ CH - C - CH - C(CH3)3 N ~
A solution of 5.05 g (0.13 mol) of sodium boranate in 100 ml of water was added dropwise to 61.5 g (0.19 mol) of 4~4-dimethyl-2-(1,2,4-triazol-1-yl)-1-(4-trifluoro-methylphenyl)-pent-l-en-3-one, in the form of the E/Z
isomer mixture, and 14.1 g (0.1275 mol) of calcium chloride in 400 ml of isopropanol at -5C. After 15 hours, 60 ml of acetone were added dro~wise. After evaporating off the solvent, the residue which remained was stirred into water and the mixture was extracted with ethyl acetate. The solution was dried over sodium sulphate, filtered and evaporated in vacuo. 60.3 g (97% of theory) of 4,4-dimethyl-2-(1,2,4-tria~ol-1-yl)-1-(4-trifluoromethylphenyl)-pent-1-en-3-ol were obtained as the E/Z isomer mixture, of melting point 54-55C.
The following compounds of the general formula (I) were obtained analogously:
Table l - CH = IC - CH - C(CH3)3 (I) n jN p N

.

Le A 20 641 y ~

~ lB907S

Ex-ample Xm Yn Melting point (C) or No. refractive index (n20) ,

4 4-OH - 168 (E/Z mixture) 4-oH 3-OCH3 136 (E/Z mixture) 6 2-OH 3,s-C12 158 (E/Z mixture) 7 4-N(CH3) - 140 (E/Z mixture) 8 4-o-CH2- ~ - 109 (E/Z mixture) 9 4-N2 -I26 (Z isomer) 4-N02 -188 (E isomer) 11 4-GF3 2-C1142 (Z isomer) 12 4-CF3 2-C1134 (E isomer) 13 4-oCF3 -113 (Z isomer) 14 4-oCF3 -108 (E isomer) 4-SCF3 -95 (Z isomer) 16 4-SCF3 -Oil (E isomer) 17 4-CF3 -128 (Z isomer) 18 4-CF3 -130 (E isomer) 19 4-CF3 3-C1130 (Z isomer) 4-CF3 3-C1141 (E isomer) 21 4-oCF3 3-Cl110 (Z isomer) 22 4-oCF3 3-Cl91 (E isomer) 23 3-No2 4-C1150 (Z isomer) 24 3-N0 4-ClResin (E isomer) 3-CF3 -120 (Z isomer) 26 3-CF3 -1.5080 (E isomer) 27 . 4 CH3Coo- _ 130 (E isomer) ~he following starting compounds of the formula (II) were obtained analogously to Example 1 and analogously to the process described in the text:
v

5 : ~able 2 A~
:
~ CH - C - CO - C(CH3)3 (II) .~. "
; N ll .. Le_A 20 641 --:

:
.~ . -, ' ~ ' , :

, ~. ~

~ 1~9~7~

Ex-ample Xm Yn r~elting point (C) or No. refractive index (n20) __ . _ _ II-3 4-OH - 186 (E isomer) II-4 4-N02 - 125 (E isomer) II-5 4-oH 3-OCH3 134 (E/Z mixture) II-6 2-OH 3~5-C1 210 (E/Z mixture) II-7 4-M(CH3)2 - 112 (E/Z mixture) 3 4-o-CH2 ~ - 120 (E/Z mixture) II-9 4-CF3 - 119 (E isom.er) II-10 4-CF3 2-C1 1.5134 (E/Z mixture) II-11 4-o-CF3 - 98 (E isomer) II-12 4-oCF3 - 1.5145 (E/Z mixture) II-13 4-CF3 3-C1 1.5236 (E/Z mixture) II-14 4-oCF3 3-C1 1.5195 (E/Z mixture) II-15 3-CF3 - 1.5220 (E/Z mixture) II-16 3-CF3 - 1.5168 (E isomer) II-17 4 CH3COO- - 95 (E isomer~
; The plant growth regulant and funglcidal 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:

0~1 (A) = ~CH=~-CH-C(CH3 )3 N

:

~ I,e A 20 641 ~' .
' , ~ 16~07~

~H
(B) = F- ~ - CH = C - CH - C(CH3)3 ~ ~ N
N~!
Cl OH
(C) - Cl- ~ - CH = C - ~H - C(CH3)3 ~j'N~N
N
Example A
- Inhibition of growth of gra~s (Festuca pratensi's) Solvent: 30 parts by weight of dimethylformamide Emulsifier: l part by weight of polyoxyethylene sorbitane monolaurate To produce a suitable preparation of active compound, 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.
Grass tFestuca pratensis) was grown in a greenhou~e up to a height in growth of 5 cm. In this stage, the plants were sprayed with the preparations of active com-pound until dripping wet. After 3 weeks, the additional ; 15 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.
; 20 In this test, active compounds (12), (18), (lO), (14) and (3) exhibited a better inhibition of growth than ' the compounds (A), (B) and (C) known from the prior art.
Exa'mp'le B
~ ~ .
'Inhibition'of ~rowth~'o'~ barley Solvent: 30 parts by weight of dimethylformamide ~Emulslfier: l part by weight of polyoxyethylene sorbitane ' monolaurate To produce a suitable preparation of active compound, :,: : :
;~ `, 1e A 20' 6'4I -:~ ::

~' ", : - ~ . ' ' ' , .

:: :
, .
.

l part by wei~ht of active co~pound was ~ixed with the stated amount of sol~ent and emulsifier ar.d the mixture was made up to the desired concentration with water.
Barley plants were grown in a greenhouse to the 2-~5 leaf stage. In this stage, the plants were sprayed with ;the preparations of active compound until dripping wet.
After 3 weeks, t~e additional growth was measured on all plants and the inhibition of growth in per cent of the additional growth of the control plants was calculated.
100% ~hibition of growth meant that growth had stopped and 0~ de-noted a growth correspondmg to that of the control plants.
In this test~ active ccmpound (18) exhibited a better inhibition of growth than the co~pounds (A~
and (C) known from the prior art.
Examp~e C
. .. ~ . .~
Inh bition of growth o~ cotton Solvent: 30 parts by weight of dimethylformamide Emulsifier: l part by weight of polyoxyethylene sorbitane monolaurate To produce a suitable preparation of active compound, l part by weight of active compound was mixed with the ` stated amount 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 ; 25 5th 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 of the plants was measured and the inhibi-tion 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% d?noted a growth i corresponding to that of the control plants.
In this test, active compounds (9), (14), (ll)~ (6), (10), (18), (lZ)~ (lS) and ~12~ exhibited a better inhibition of growth than the compounds (A), (~) and (C) r~ ' Le A 20 641 ~ -r~
.
, ' ~ ~

.

known from the prior art.
Example D
Inhibition of growth of soya beans Solvent: 10 parts by weight of dimethylformamide Emulsifier: 2 parts by weight cf polyoxyethylere scrbitane 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.
Young soya bean plants, in the stage in which the first secondary leaves had unfolded, were sprayed with the preparations of active compound until dripping wet.
After 2 weeks, the additional growth was measured and the inhibition of growth in % of the additional growth of the control plants was calculated. 100% meant that growth had stopped and C% denoted a growth correspor.ding to that of the untreated control plants.
In this test3 active compounds (3), (9), (14), (11), (10), (18), (17), (15) and (12) exhibited a better inhibi-tion of growth than the compound (A) known from the prior-art.
Example E
Inhibition of 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 mi~ed withthe stated amounts of solvent and emulsifier and the mixture was made up to the ~esired concent aticn with water.
Sugar beet plants were grown in a greenhouse until formation of the cotyledons was complete. In this stage, Le A 20 641 ~ 1~90~5 the plants were sprayed with the preparations of active compound until dripping wet. Ater 14 days, the additional grcwth of the plants was measured and the inhibition of growth in per cent of the additional growth of the control plants was calculated. 0% inhibition of growth denoted a growth which corresponded to that of the control plants. 100% inhibition of growth meant that gr~th had stopped.
In this test, active co~pounds (3), ~9), (14), (11), (]0), (18), (17), (15) and (12) exhibited a better inhibition of growth than the com~ounds (A) and (B) known from the prior art.
Exam~ e F
Fbrmat1on c~ ~ethylene ; Solvent: 30 parts by weight of dimethylformamide Emulsifier: 1 part by weight of polyoxyethylene sorbitane monolaurate To produce a suitable preparation of active compound, 1 part by weight of active co~pound was mixed with the stated amounts of solvent and emulsifier and the mixture was made up to the desired concentration with water.
Pieces of leaf of identical size were punched from soya bean leaves.
These were introduced into vessels which could be closed air-tight, together with 1 ml of the p~eparation of active ccmpound or control solution. After 24 hours the ethylene which had collected in the vessels was determined by customary methods of detection. The evolution of ethylene from the pieces of leaf treated with the preparations of active compound was cc~pared with the evolution of ethylene of the controls.
The figures of merit had the follcwing meanings:
0 denoted evolution of ethylene as in the case of the con-trol + denoted slightly increased evolution of ethylene ++ denoted greatly increased evolution of ethylene +++ denoted very greatly increased e~olution of ethylene ,., ~

l ~6~75 In this test, active compounds (3) and (9) caused more formation of ethylene than the compounds (A) and (B) known from the pricr art.
Example G Sti~ulation of photosynthesis ..
After treatment of soya bean plants with the active compounds (13), (11) and (14), a stimulation of photosynthesis compared to control plants was found. In contrast, treatment with the known compound (A) did not produce this effect.
Examp'l'e H
Erysiphe test (barley)/protective/
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 concen-tration.
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 tem-perature of about 20C and a relative atmospheric humidity of 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 (A) ~nown from the prior art was ~shown, for example, by the compounds (3), (9), (10), (11), (12), (14), (15) and (18).
~ ~5 Exa'mp'l'e' I

''~ Le' A 20 641 .

.

~ 169~7~
Powdery mildew of barley test (Erysiphe graminis var. hordei)/systemic (fungal disease of cereal shoots) The active compounds were used as pulverulent seed treatment agentsD
These were pro~uced by extending the active compound with a mixture of equal parts by weight of talc and kieselgur to give a finely pulverulent mixture of the desired concentration of active compound.
For the treatment of seed, barley seed was shaken with the extended active compound in a closed glass bottle. The seed was sown at the rate of 3 x 12 grains in flowerpots, 2 cm deep in a mixture of one part by volume of Fruhstorfer standard soil and one part by volume of quart~ sand. The germina-tion and emergence took place under favourable conditions in a greenhouse. 7 ; days after sowing, when the barley plants had unfolded their first leaf, they were dusted with fresh spores of Erysiphe graminis var. hordei and grown on at 21 to 22C and 80 to 90% relative atmospheric humidity and 16 hours' exposure tolight. The typical mildew pustules formed on the leaves within 6 days.
me degree of infection was expressed as a percentage of the infection of the untreated control plants. mus, 0% denoted no infection and 100~ denoted the same degree of infection as in the case of the untreated control. The m~re active was the active compound, the lower was the degree of mlldew infection.
In this test, a clearly superior activity compared with the compounds (A) and (C) known from the prior art was shcwn, for example, by the compounds (3), (9) and (10).
Example J
Seed dressing test/stripe disease of barley (seed-borne mycosis) To produce a suitable dry dressing, the active compound was extended ; with a mixture of equal parts by weigh-t ~ ~9~75 of talc and kieselgur to give a finely powdered mixture with the desired concentration of active compGund.
To apply the dressing, barley seed, which was naturally infected by Drechslera grarr.inea (comrronly described as ~elminthosporium gramineum), was shaken with the dressing in a closed glass fla.sk. The seed, on moist filter paper discs in closed Petri dishes, was exposed to a temperature of 4C for 10 days in a refrigerator. The gerrrlnation of the barley, and possibly also of the fungus spores, was thereby initiated.
2 batches of 50 grains of the pre-gerrrlinated barley were subsequently sown 3 cm deep in Fruhstorfer standard soil and cultivated in a greenhouse at temperatures of about 18C in seed boxes which were exposed to light for 16 hours daily. The typical symptoms of the stripe disease developed within 3 to 4 weeks.
4fter this time, the number of diseased plants was determined as a percentage of the total number of emerged plants. The fewer were the plants diseased, the more effective was the active compound.
In this test, a cleàrly superior activity compared with the compound (A) known from the prior art was shown, for example, by the compound 3).

.
.' .
:- .

.

~ Le A 20 641 :
~ - .

., .
' ......
, ,~

,

Claims (36)

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

1. A substituted 1-phenyl-2-triazolyl-pent-1-en-3-ol of the formula (I) in which X represents a halogenoalkyl, halogenoalkoxy, halogenalkylthio, nitro, hydroxyl, dialkylamino or alkylcarbonyloxy radical, or represents a benzyloxy radical optionally substituted in the phenyl moiety by substituents selected from fluorine, chlorine, bromine and alkyl, Y represents a halogen atom, an alkyl, alkoxy or cyano radical or a phenyl or phenoxy radical optionally substituted by substituent selected from fluorine, chlorine, bromine and alkyl, m is 1, 2 or 3, n is 0, 1, 2, 3 or 4, and m + n = 1 to 5, or a non-phytotoxic acid addition salt or metal salt complex thereof wherein the metal is selected from those of main groups II to IV and of sub-groups I, II and IV to VIII of the periodic table.

2, A compound according to claim 1, in which X represents a halogeno-alkoxy, halogenalkylthio, alkylthio, hydroxyl, dialkylamino or alkylcarbony-loxy radical, or represents a benzyloxy radical optionally substituted in the phenyl moiety by substituents selected from fluorine, chlorine, bromine and alkyl.

3. A compound according to claim 1, in which X represents a halo-genoalkyl or nitro radical.

4. A compound according to claim 2, in which X represents a halo-genoalkoxy or halogenoalkylthio radical, each with 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms, an alkylthio radical with 1 to 4 carbon atoms, a hydroxyl radical, a dialkylamino radical with 1 to 4 carbon atoms in each alkyl part, an alkylcarbonyloxy radical with 1 to 4 carbon atoms in the alkyl part, or a benzyloxy which is optionally substituted in the phenyl moiety by substituent(s) selected from fluorine, chlorine, bromine and alkyl with 1 or 2 carbon atoms, Y represents a fluorine, chlorine or bromine atom, an alkyl radical with 1 to 4 carbon atoms, an alkoxy radical with 1 to 4 carbon atoms, a cyano radical, a phenyl which is optionally sub-stituted by substituent(s) selected from fluorine, chlorine, bromine and alkyl with 1 or 2 carbon atoms, or phenoxy which is optionally substituted by substituent(s) selected from fluorine, chlorine, bromine and alkyl with 1 or 2 carbon atoms, m is 1 or 2 and n is 0, 1, 2 or 3.

5. A compound according to claim 3, in which X represents a halogeno-alkyl radical with 1 or 2 carbon atoms and 1 to 5 identical or different halogen atoms or represents a nitro radical, Y represents a fluorine, chlorine atom, an alkyl radical with 1 to 4 carbon atoms, an alkoxy radical with 1 to 4 carbon atoms, a cyano radical, a phenyl which is optionally substituted by substituent(s) selected from fluorine, chlorine, bromine and alkyl with 1 or 2 carbon atoms, or phenoxy which is optionally substituted by substituent(s) selected from fluorine, chlorine, bromine and alkyl with 1 or 2 carbon atoms, m is 1 or 2 and n is 0, 1, 2 or 3.

6. A compound according to claim 2, in which X represents a trifluoro-methoxy or trifluoromethylthio radical, a 1,1,2-trifluoro-2-chloroethoxy or -ethylthio radical, a methylthio, hydroxyl, dimethylamino, acetoxy or tert.-butylcarbonyloxy radical or a benzyloxy radical which optionally has one or two identical or different substituents selected from fluorine, chlorine and methyl, Y represents a fluorine or chlorine atom or a methyl, ethyl, iso-propyl, tert.-butyl, methoxy, isopropoxy or cyano radical, or a phenyl or phenoxy radical which optionally has one or two identical or different sub-stituents selected from fluorine, chlorine and methyl, m is 1 or 2 and n is 0, 1 or 2.

7. A compound according to claim 3, in which X represents a trifluoro-methyl, difluoromethyl, fluorodichloromethyl, trichloromethyl, or 1,1,2-trifluoro-2-chloroethyl radical or represents a nitro radical, Y represents a fluorine or chlorine atom or a methyl, ethyl, isopropyl, tert.-butyl, methoxy, isopropoxy or cyano radical, or a phenyl or phenoxy radical which optionally has one or two identical or different substituents selected from fluorine, chlorine and methyl, m 1 or 2 and n is 0, 1 or 2.

8. A compound according to claim 2, in which X represents a 4-tri-fluoromethoxy, 4-trifluoromethylthio, 2- or 4-hydroxy, 4-dimethylamino, 4-acetoxy, or 4-benzyloxy radical, Y represents a 2-, 3 (or 5)- or 4- chlorine atom, or a 3-methoxy radical, m is 1 and n is 0, 1 or 2.

9. A compound according to claim 3, in which X represents a 2-, 3- or 4-trifluoromethyl radical or a 3- or 4-nitro radical, Y represents a 2-, 3-or 4-chlorine atom, m is 1 and n is 0 or 1.

10. The Z isomer of 4,4-dimethyl-2-(1,2,4-triazol-1-yl)-1-(4-tri-fluoromethoxyphenyl)-pent-1-en=3-ol of the formula

11. The E isomer of 4,4-dimethyl-2-(1,2,4-triazolyl-yl)-1-(4-tri-fluoro methoxyphenyl)-pent-1-en-3-ol of the formula

12. The Z isomer of 4,4-dimethyl-2-(1,2,4-triazol-1-yl)-1-(3-chloro-4-trifluoromethoxyphenyl)-pent-1-en-3-ol of the formula

13. The E isomer of 4,4-dimethyl-2-(1,2,4-triazol-1-yl)-1-(3-chloro-4-trifluoromethoxyphenyl)-pent-1-en-3-ol of the formula

14. A process for the production of a compound according to claim 1, characterised in that a 1-phenyl-2-triazolyl-pent-1-en-3-one of the general formula (II) in which X, Y, n and m have the abovementioned meaning, is reduced and, where required, the compound obtained, of the formula (I), is subsequently subjected to an addition reaction with a suitable acid or a suitable metal salt.

15. A method of combating fungi or of regulating the growth of plants comprising applying to the fungi, or to a habitat thereof, a fungicidally or plant growth regulating effective amount of a compound according to claim 1.

16. A method according to claim 15 wherein the compound is applied to combat fungi.

17. A method according to claim 15 wherein the compound is applied as a growth regulator.

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

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

20, A method according to claim 18, characterised in that a composition is used containing from 1 to 0.0001% of the active compound, by weight.

21. A method according to claim 18, characterised in that a composition is used containing from 0.5 to 0.001% of the active compound, by weight.

22. A method according to claim 17 or 19, characterised in that the active compound is applied to an area of agriculture in an amount of 0.01 to 50 kg per hectare.

23. A method according to claim 17 or 19, characterised in that the active compound is applied to an area of agriculture in an amount of 0.05 to 10 kg per hectare.

24. A method according to claim 16 or 18, characterised in that the active compound is applied to soil in an amount of 0.00001 to 0.1 per cent by weight.

25. A method according to claim 16 or 18, characterised in that the active compound is applied to soil in an amount of 0.0001 to 0.02 per cent by weight.

26. A method according to claim 16 or 18, characterised in that the active compound is applied to seed in an amount of 0.001 to 50 g per kg of seed.

27. A method according to claim 16 or 18, characterised in that the active compound is applied to seed in an amount of 0.01 to 10 g per kg of seed.

28. A method according to claim 16 or 18 wherein the compound is the compound according to claim 10.

29. A method according to claim 16 or 18 wherein the compound is the compound according to claim 11.

30. A method according to claim 16 or 18 wherein the compound is the compound according to claim 13.

31. A method according to claim 16 or 18 wherein the compound is the compound according to claim 14.

32. A process according to claim 14, wherein in the starting material of formula (II), Y represents a halogenoalkoxy, halogenalkylthio, alkylthio, hydroxyl, dialkylamino or alkylcarbonyloxy radical, or represents a benzyloxy radical optionally substituted in the phenyl moiety by substituents selected from fluorine, chlorine, bromine and alkyl.

33. A process according to claim 14, wherein in the starting material of formula (II), Y represents a halogenoalkyl or nitro radical.

34. A process according to claim 32 or 33, wherein the keto group in the starting material of formula (II) is reduced to a hydroxyl group using a complex hydride in a diluent.

35. A method according to claim 16 or 17 wherein a compound according to claim 5 is used.

36. A method according to claim 16 or 17, wherein a compound according to claim 5 is used.