DE4022784A1 - New azolyl:methyl-substd. cyclic alcohol derivs. - Google Patents

Abstract

(A)Azolylmethyl-substd. cyclic alcohols of formula (I) and their acid-addn. salts and metal complexes are new. X= CH or N; T= (CH2)n, CR11R12, O or S; n= 1-5; R1 and R5= H or 1-4C alkyl, or CR1R5= C=CHR7 or CHZR'7; Z=CH2, O, SO, SO, SO2 or NR8; R7= (a) 1-8C alkyl, phenyl, biphenylyl, naphthyl, benzyl or 3-8C cycloalkyl, all opt. substd. by 1-3 of halogen, NO2, OPh, NH2, 1-4C alkyl, 1-4C alkoxy, or 1-4C haloalkyl, or (b) tetrahydropyranyl; R'7= H or R7; R2 and R3= H or 1-4C alkyl, or CR2R3 may be C=CHR7 when CR1R5 is C=CHR7; R4 and R8= H or 1-4C alkyl; or R3+R4 completes a satd. or unsatd. 5-6C carbocyclic ring; R6 and R9-R12= 1-8C alkyl, phenyl, biphenylyl, naphthyl, heteroaryl, benzyl, dioxolanyl or 3-8C cycloalkyl, all opt. substd. by 1-3 of halogen, NO2, OPh, NH2, 1-4C alkyl, 1-4C alkoxy or 1-4C haloalkyl; or R2+R3+R4+R9 completes an opt. halo-substd. benzene ring; etc.

Description

The present invention relates to valuable new azolylmethylcycloalkanols, plant protection products containing them, in particular fungicides and growth regulators and processes for their manufacture.

It is known 1- (1,2,4-triazol-1-yl-methyl) -2- (4-chlorobenzyl) cyclohexan-1-ol (EP 3 24 646) to use as a fungicide. The fungicidal effects however, are not satisfactory in all cases.

The invention was therefore based on the object of using new azole compounds provide better fungicidal and growth regulatory effects.

It has now been found that new azolylcycloalkanols of the general Formula I.

in which
R¹ and R² are the same or different and represent hydrogen or C₁ to C₄ alkyl;
Y is C₁ to C₈ alkyl, phenyl, biphenyl, naphthyl, heteroaryl, benzyl, dioxolanyl or C₃ to C₈ cycloalkyl, each of these radicals being monosubstituted to triple by halogen, nitro, phenoxy, amino, C₁ to C₄alkyl , C₁ to C₄ alkoxy or C₁ to C₄ haloalkyl may be substituted;
X represents CH or N,
and their plant-compatible acid addition salts and metal complexes have a better fungicidal action than the known compounds.

The new azolylmethylcycloalkanols of the general formula I are obtained i. a. in the form of racemates or diastereomer mixtures. These isomers can be in the usual way, for example because of their solubility or the solubility of their salts or also by column chromatography, separate and isolate in pure form. From such an isolated diastereomer can be obtained with known methods uniform enantiomers. The present invention encompasses both the new isomers and also their mixtures and their use as fungicides or growth regulators.

Both the individual diastereomers or Enantiomers as well as their i. a. resulting mixtures be used.

Preferred are those azolylmethylcycloalkanols I in which the radical Y has the following meaning:
C₁ to C₈ alkyl, preferably C₁ to C₄ alkyl, especially methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl and tert-butyl; of the C₁ to C₈ alkyl radicals which have more than 4 carbon atoms, n-pentyl and neopentyl are to be mentioned as preferred;
Phenyl and halogen-substituted phenyl such as 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl as well as 2-bromophenyl, 3-bromophenyl and 4-bromophenyl, 2,3-dichlorophenyl, 2,4 -Dichlorophenyl, 2,5-dichlorophenyl and 2,6-dichlorophenyl as well as 2-chloro-4-fluorophenyl and 2-chloro-6-fluorophenyl;
phenyl simply substituted by nitro, phenoxy, amino or C₁ to C₄ alkyl groups, such as 3-nitrophenyl, 4-nitrophenyl, 3-phenoxyphenyl, 4-phenoxyphenyl, 3-aminophenyl and 4-aminophenyl and 4-ethylphenyl, 4 -Isopropylphenyl and 4-tert-butylphenyl;
phenyl substituted by two or three of the above-mentioned but different radicals, such as 2-chloro-6-methylphenyl;
phenyl substituted once or twice by C₁ to C₄ alkoxy groups, such as 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 4-tert-butyloxyphenyl and 2,4-dimethoxyphenyl and 3,4-dimethoxyphenyl;
triple halogen substituted methylphenyl such as 2-trifluoromethyl, 3-trifluoromethyl and 4-trifluoromethylphenyl;
p-biphenyl;
1-naphthyl and 2-naphthyl;
Heteroaryl with 5 or 6 ring atoms, in particular 6 rings with up to three nitrogen atoms, such as pyridyl, 2-pyridyl, 3-pyridyl and 4-pyridyl, and 5 rings with preferably one or two of the heteroatoms O, S and N, especially furyl, 2-furyl, thienyl, 2-thienyl, 3-thienyl, 4-oxazolyl, 4-thiazolyl, 4-isoxazolyl, 5-isoxazolyl and 5-imidazolyl;
Benzyl;
Dioxolanyl, preferably 1,3-dioxolan-2-yl;
C₃- to C₈-cycloalkyl, preferably cyclopentyl and cyclohexyl.

The radicals R¹ and R² can independently of one another be the same or different , they preferably each represent a hydrogen atom or one n-alkyl radical with 1 to 4 carbon atoms, especially methyl.

The plant-compatible salts of are suitable as acid addition salts acids that do not impair the fungicidal activity of I, so z. B. hydrochlorides, bromides, sulfates, nitrates, phosphates, oxalates and Dodecylbenzenesulfonates. However, since the effectiveness of the salts on the cation goes back, it comes down to the anion i. a. not at. The active ingredient salts are useful by reacting the Azolylmethylcycloalkanole (I) with the acids.

Metal complexes of the new compounds I or their salts are preferred with metals of the 2nd main group such as magnesium or calcium, the 3rd and IV. Main group such as aluminum, tin or lead or with metals from I. to VIII. Subgroup formed, the subgroup elements of the 4th period copper, zinc, manganese, iron, cobalt are particularly preferred and nickel. For this purpose, the azolylmethylcycloalkanols with appropriate Metal salts implemented.

The new azolylmethylcycloalkanols I are prepared i. a. by Implementation of a compound of general formula II

in which Y, R¹ and R² have the meanings given above, with a Compound of the general formula III

in which Me represents a hydrogen or a metal atom and X is CH or N means, and, if appropriate, the compounds thus obtained with plant-compatible acids in their salts or in their metal complexes transferred.

Of the compounds III, preference is given to those in which Me is for one Hydrogen atom or an alkali metal atom, especially sodium or Potassium stands.

If Me represents a hydrogen atom, a weight ratio is appropriate Compounds III: II from 2: 1 to 6: 1 are observed, in particular about 3: 1. The reaction is optionally carried out in the presence of a solution or diluent, advantageously with the addition of an inorganic or organic base and optionally with the addition of a reaction accelerator. Preferred solvents and diluents include ketones such as acetone, methyl ethyl ketone or cyclohexanone, nitriles such as acetonitrile or propionitrile, alcohols such as methanol, ethanol, isopropanol, n-butanol or glycol, esters such as ethyl acetate, methyl acetate or Butyl acetate, ethers such as tetrahydrofuran, diethyl ether, dimethoxyethane, Dioxane or diisopropyl ether, amides such as dimethylformamide, dimethylacetamide or N-methylpyrrolidone, sulfolane or corresponding mixtures.

Suitable bases, which may also be used as acid-binding agents in the Reaction can be used, for example, alkali metal hydroxide such as Lithium, sodium or potassium hydroxide, alkali carbonates such as sodium or Potassium carbonate or sodium or potassium hydrogen carbonate, pyridine or 4-dimethylaminopyridine. However, other common bases can also be used will.

Preferably metal halides such as Sodium iodide, or potassium iodide, quaternary ammonium salts such as tetrabutylammonium chloride, bromide or iodide or crown ether such as 12-crown-4, 15-crown-5, 18-crown-6 or dicyclohexano-18-crown-6 in question.

The reaction is generally carried out at temperatures between 10 and 150 ° C. in particular between 20 and 120 ° C, unpressurized or under pressure, continuously or carried out discontinuously.  

If Me stands for a metal atom, then a weight ratio III: II of 1: 1 up to 3: 1, in particular 1: 1 preferred. The implementation takes place if necessary in the presence of a solvent or diluent and, if appropriate with the addition of an inorganic or organic base. Among the preferred Solvents and diluents include amides such as dimethylformamide, dieethylformamide, Dimethylacetamide, N-methylpyrrolidone, hexamethylphosphoric triamide, Sulfoxides such as dimethyl sulfoxide and finally sulfolane.

Suitable bases, which may also be used as acid-binding agents in the Reaction can be used, for example, alkali metal hydrides such as Lithium, sodium and potassium hydride, alkali amides such as sodium and potassium amide, also sodium or potassium tert-butoxide.

The procedure is generally between -10 and 120 ° C, preferably at 20 up to 80 ° C. In the presence of a solvent, the boiling point is expedient of the respective solvent worked.

The starting compounds II can be simplified by known methods Wise from the ketones of formula IV

produce, e.g. B. by reaction with trimethylsulfonium methyl sulfate (cf. Corey, Chaykovsky, J. Chem. Soc. 1962, 64, 3782).

The compounds IV can be prepared according to generally known methods (see G. F. Woods, I. W. Tucker, J. Am. Chem. Soc. 1948, 70, 2174 and A. S, Cieplak et al. J. Am. Chem. Soc. 1989, 111, 8447).

Examples of compounds II are listed in Table I.

The compounds of general formula I and their salts and metal complexes are suitable as fungicides and growth regulators with good Plant tolerance.

Manufacturing examples Regulation 1 4- (4-chlorophenyl) -1-oxa-bicyclo [0.2.5] octane (Compound No. 1, Table 1)

To a solution of 30 g (0.14 mol) of 3- (4-chlorophenyl) cyclohexanone in 100 ml Methylene chloride was mixed with 54.4 g (0.30 mol) of trimethylsulfonium methyl sulfate and 50 ml of sodium hydroxide solution (50%). After the reaction mixture The solution was stirred for 12 hours at room temperature (20 ° C) 100 ml of water are added and the organic phase is separated off. The organic Phase was washed twice with water, dried over sodium sulfate and constricted.

Yield: 28.2 g (91%)

example 1 1- (1,2,4-triazol-1-ylmethyl) -3- (4-chlorophenyl) cyclohexan-1-ol (Compound no.1.1, table 2)

A solution of 11.3 g (0.16 mol) of triazole in 100 ml of N, N-dimethylformamide 12.4 g of sodium hydroxide solution (50% by weight) were added and the mixture was left on for 30 minutes Heated to 50 ° C. 18.2 g (0.08 mol) of 4- (4-chlorophenyl) -1-oxa-bicyclo [0.2.5] octane, that in 20 ml of N, N-dimethylformamide was solved, added dropwise. After the reaction mixture at 15 hours After stirring at room temperature, 100 ml of water was added to the solution and shaken out several times with methyl tert-butyl ether. The organic Phase was washed twice with water, dried over sodium sulfate and constricted. By crystallizing the residue from methyl tert-butyl ether / n-hexane the product was obtained as a 2: 1 mixture of diastereomers.  

Yield 20.3 g (87%)
Melting point: 128 to 130 ° C

According to regulation 1, those listed in table 1 can Compounds are prepared and according to Example 1 which in the Compounds listed in Table 2.  

Table 1

Table 2

The fungicidal and growth-regulating compounds or those containing them Agents can for example be in the form of directly sprayable Solutions, powders, suspensions, also high-proof aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, Pastes, dusts, sprinkles or granules by spraying, Nebulization, dusting, scattering or pouring can be used. The Forms of use depend on the purposes; they should be in in any case, the finest possible distribution of the active compounds according to the invention guarantee.

Usually the plants are sprayed with the active ingredients or pollinated or treated the seeds of the plants with the active ingredients.

The formulations are prepared in a known manner, e.g. B. by Stretching the active ingredient with solvents and / or carriers, if desired, using emulsifiers and dispersants, in the case of water as a diluent also other organic Solvents can be used as auxiliary solvents. As Auxiliaries are essentially considered here: solvents such as Aromatics (e.g. xylene), chlorinated aromatics (e.g. chlorobenzenes), paraffins (e.g. petroleum fractions), alcohols (e.g. methanol, butanol), ketones (e.g. Cyclohexanone), amines (e.g. ethanolamine, dimethylformamide) and water; Carriers such as natural stone powder (e.g. kaolins, clays, talc, Chalk) and synthetic stone powder (e.g. highly disperse silica, Silicates); Emulsifiers such as nonionic and anionic emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkali sulfonates and aryl sulfonates) and dispersants such as lignin sulfite liquor and methyl cellulose.

The alkali, alkaline earth, ammonium salts come as surface-active substances of aromatic sulfonic acids, e.g. B. lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, as well as fatty acids, alkyl and alkylarylsulfonates, Alkyl, lauryl ether and fatty alcohol sulfates, and salts sulfated hexa-, hepta- and octadecanols, as well as fatty alcohol glycol ether, Condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl or nonylphenol, alkylphenol, Tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, Fatty alcohol ethylene oxide condensates, ethoxylated castor oil, Polyoxyethylene alkyl ether or polyoxypropylene, lauryl alcohol polyglycol ether acetate, Sorbitol esters, lignin sulfite waste liquors or methyl cellulose in Consider.  

Powders, materials for spreading and dusts can be mixed or combined Grinding the active substances with a solid carrier will.

Granules, e.g. B. coating, impregnation and homogeneous granules by binding the active ingredients to solid carriers. Solid carriers are mineral earths such as silica gel, silicas, silica gels, Silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, Dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground Plastics, fertilizers, such as ammonium sulfate, ammonium phosphate, Ammonium nitrate, ureas and vegetable products such as corn flour, Tree bark, wood and nutshell flour, cellulose powder or other solid Carriers.

Examples of such preparations are:

• I. a solution of 90 parts by weight of compound no. 1.1 and 10 parts by weight of N-methyl-α-pyrrolidone for use in the form smallest drop is suitable;
• II. A mixture of 20 parts by weight of compound no. 1.2, 80 parts by weight Xylene, 10 parts by weight of the adduct from 8 to 10 moles of ethylene oxide in 1 mole of oleic acid-N-monoethanolamide, 5 parts by weight Calcium salt of dodecylbenzenesulfonic acid, 5 parts by weight of the adduct and 40 moles of ethylene oxide to 1 mole Castor oil; by finely distributing the solution in water a dispersion.
• III. an aqueous dispersion of 20 parts by weight of the compound No. 1.56, 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 40 mol of ethylene oxide 1 mol castor oil;
• IV. An aqueous dispersion of 20 parts by weight of the compound No. 1.57, 25 parts by weight of cyclohexanol, 65 parts by weight of one Mineral oil fraction with a boiling point of 210 to 280 ° C and 10 parts by weight of the adduct of 40 moles of ethylene oxide with 1 mole Castor oil;
• V. a mixture of 80 parts by weight ground in a hammer mill Compound No. 1.61, 3 parts by weight of the sodium salt of Diisobutylnaphthalene-α-sulfonic acid, 10 parts by weight of the sodium salt  a lignosulphonic acid from a sulphite waste liquor and 7 parts by weight of powdered silica gel; through fine distribution a spray mixture is obtained from the mixture in water;
• VI. an intimate mixture of 3 parts by weight of compound no. 1.62 and 97 parts by weight of finely divided kaolin; this dusts contains 3% by weight of active ingredient;
• VII. An intimate mixture of 30 parts by weight of compound no. 1.89, 92 parts by weight of powdered silica gel and 8 parts by weight Paraffin oil that is on the surface of this silica gel was sprayed; this preparation gives the active ingredient a good one Adherence;
• VIII. A stable aqueous dispersion of 40 parts by weight of the compound No. 1.90, 10 parts by weight of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts by weight of silica gel and 48 parts by weight of water, which can be further diluted;
• IX. a stable oily dispersion of 20 parts by weight of the compound No. 1.1, 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of fatty alcohol polyglycol ether, 20 parts by weight the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil.

The new compounds are characterized by excellent effectiveness against a wide range of phytopathogenic fungi, especially from the class of Ascomycetes and Basidiomycetes. They are partly systemically effective and can be used as leaf and soil fungicides will.

They are particularly important for combating a large number of fungi on various crops such as wheat, rye, barley, oats, rice, Corn, grass, cotton, soybeans, coffee, sugar cane, wine, fruit and ornamental plants and vegetables such as cucumbers, beans and squashes, as well on the seeds of these plants.

The compounds are applied by looking at the mushrooms or the front Fungus to protect seeds, plants, materials or the Soil treated with a fungicidally effective amount of the active ingredients.

The application takes place before or after the infection of the materials, Plants or seeds through fungi.  

The compounds I are particularly suitable for controlling the following plant diseases:
Erysiphe graminis (powdery mildew) in cereals,
Erysiphe cichoracearum and Sphaerotheca fuliginea on pumpkin plants,
Podosphaera leucotricha on apples,
Uncinula necator on vines,
Puccinia species on cereals,
Rhizoctonia on cotton and grass,
Ustilago species on cereals and sugar cane,
Venturia inaequalis (scab) on apples,
Helminthosporium species on cereals,
Septoria nodorum on wheat,
Botrytis cinerea (gray mold) on strawberries, vines,
Cercospora arachidicola on peanuts,
Pseudocercosporella herpotrichoides on wheat, barley,
Pyricularia oryzae on rice,
Phytophthora infestans on potatoes and tomatoes,
Fusarium and Verticillium species on different plants,
Plasmopara viticola on vines,
Alternaria species in vegetables and fruits.

The new connections can also be used in material protection (wood protection) be, e.g. B. against Paecilomyces variotii.

The fungicidal compositions generally contain between 0.1 and 95, preferably between 0.5 and 90 wt .-% active ingredient.

Depending on the type of effect desired, the application rates are between 0.02 and 3 kg of active ingredient per ha.

In the seed treatment, amounts of active ingredient are generally 0.001 up to 50 g, preferably 0.01 to 10 g per kilogram of seed is required.

The agents according to the invention can be used as fungicides also be present together with other active ingredients, the z. B. with herbicides, Insecticides, growth regulators, fungicides or even with fertilizers.

When mixed with fungicides, you get one in many cases Enlargement of the fungicidal spectrum of activity.  

The following list of fungicides with which the compounds according to the invention can be used together is intended to explain, but not to limit, the possible combinations:
Sulfur,
Dithiocarbamates and their derivatives, such as
Ferridimethyldithiocarbamate,
Zinc dimethyldithiocarbamate,
Zinc ethylene bisdithiocarbamate,
Manganese ethylene bisdithiocarbamate,
Manganese-zinc-ethylenediamine-bis-dithiocarbamate,
Tetramethylthiuram disulfide,
Ammonia complex of zinc (N, N-ethylene-bis-dithiocarbamate),
Ammonia complex of zinc (N; N'-propylene-bis-dithiocarbamate),
Zinc (N, N'-propylene-bis-dithiocarbamate),
N, N'-polypropylene bis (thiocarbamoyl) disulfide;
Nitroderivatives, such as dinitro- (1-methylheptyl) phenylcrotonate,
2-sec-butyl-4,6-dinitrophenyl-3,3-dimethylacrylate,
2-sec-butyl-4,6-dinitrophenyl-isopropyl carbonate,
5-nitro-isophthalic acid di-isopropyl ester;
heterocyclic substances, such as
2-heptadecyl-2-imidazoline acetate,
2,4-dichloro-6- (o-chloroanilino) -s-triazine,
O, O-diethyl phthalimidophosphonothioate,
5-amino-1- [bis- (dimethylamino) phosphinyl] -3-phenyl-1,2,4-triazole,
2,3-dicyano-1,4-dithioanthraquinone,
2-thio-1,3-dithiolo [4,5-b] quinoxaline,
1- (butylcarbamoyl) -2-benzimidazole-carbamic acid methyl ester,
2-methoxycarbonylamino-benzimidazole,
2- (furyl- (2)) - benzimidazole,
2- (thiazolyl- (4)) - benzimidazole,
N- (1,1,2,2-tetrachloroethylthio) tetrahydrophthalimide,
N-trichloromethylthio-tetrahydrophthalimide,
N-trichloromethylthio-phthalimide,
N-dichlorofluoromethylthio-N ′, N′-dimethyl-N-phenyl-sulfuric acid diamide, 5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole,
2-rhodanmethylthiobenzthiazole,
1,4-dichloro-2,5-dimethoxybenzene,
4- (2-chlorophenylhydrazono) -3-methyl-5-isoxazolone,
Pyridine-2-thio-1-oxide,
8-hydroxyquinoline or its copper salt,
2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiine,
2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiin-4,4-dioxide,
2-methyl-5,6-dihydro-4H-pyran-3-carboxylic acid anilide,
2-methyl-furan-3-carboxylic acid anilide,
2,5-dimethyl-furan-3-carboxylic acid anilide,
2,4,5-trimethyl-furan-3-carboxylic acid anilide,
2,5-dimethyl-furan-3-carboxylic acid cyclohexylamide,
N-cyclohexyl-N-methoxy-2,5-dimethyl-furan-3-carboxamide,
2-methylbenzoic acid anilide,
2-iodo-benzoic acid anilide,
N-formyl-N-morpholine-2,2,2-trichloroethyl acetal,
Piperazin-1,4-diylbis- (1- (2,2,2-trichloro-ethyl) -formamide,
1- (3,4-dichloroanilino) -1-formylamino-2,2,2-trichloroethane
2,6-dimethyl-N-tridecyl-morpholine or its salts,
2,6-dimethyl-N-cyclododecyl-morpholine or its salts,
N- [3- (p-tert-butylphenyl) -2-methylpropyl] cis-2,6-dimethylmorpholine, N- [3- (p-tert-butylphenyl) -2-methylpropyl] piperidine,
1- [2- (2,4-dichlorophenyl) -4-ethyl-1,3-dioxolan-2-yl-ethyl] -1H-1,2,4-t-riazole,
1- [2- (2,4-dichlorophenyl) -4-n-propyl-1,3-dioxolan-2-yl-ethyl] -1H-1,2,4-triazole,
N- (n-propyl) -N- (2,4,6-trichlorophenoxyethyl) -N'-imidazol-yl-urea,
1- (4-chlorophenoxy) -3,3-dimethyl-1- (1H-1,2,4-triazol-1-yl) -2-butanone, -
1- (4-chlorophenoxy) -3,3-dimethyl-1- (1H-1,2,4-triazol-1-yl) -2-butanol, -
α- (2-chlorophenyl) -α- (4-chlorophenyl) -5-pyrimidine-methanol,
5-butyl-2-dimethylamino-4-hydroxy-6-methyl-pyrimidine,
Bis- (p-chlorophenyl) -3-pyridinemethanol,
1,2-bis (3-ethoxycarbonyl-2-thioureido) benzene,
1,2-bis (3-methoxycarbonyl-2-thioureido) benzene,
as well as various fungicides, such as
Dodecylguanidine acetate,
3- [3- (3,5-dimethyl-2-oxycyclohexyl) -2-hydroxyethyl] glutarimide,
Hexachlorobenzene,
DL-methyl-N- (2,6-dimethyl-phenyl) -N-furoyl (2) -alaninate,
DL-N- (2,6-dimethylphenyl) -N- (2'-methoxyacetyl) alanine methyl ester,
N- (2,6-dimethylphenyl) -N-chloroacetyl-D, L-2-aminobutyrolactone,
DL-N- (2,6-dimethylphenyl) -N- (phenylacetyl) alanine methyl ester,
5-methyl-5-vinyl-3- (3,5-dichlorophenyl) -2,4-dioxo-1,3-oxazolidine,
3- [3,5-dichlorophenyl- (5-methyl-5-methoxymethyl] -1,3-oxazolidine-2,4-d-ion,
3- (3,5-dichlorophenyl) -1-isopropylcarbamoylhydantoin,
N- (3,5-dichlorophenyl) -1,2-dimethylcyclopropane-1,2-dicarboximide, -,
2-cyano- [N- (ethylaminocarbonyl) -2-methoximino] acetamide,
1- [2- (2,4-dichlorophenyl) pentyl] -1H-1,2,4-triazole,
2,4-difluoro-α- (1H-1,2,4-triazolyl-1-methyl) -benzhydryl alcohol,
N- (3-chloro-2,6-dinitro-4-trifluoromethyl-phenyl) -5-trifluoromethyl-3-c-chloro-2-aminopyridine,
1 - ((bis- (4-Fluorophenyl) methylsilyl) methyl) -1H-1,2,4-triazole.

Claims (10)

1. Azolylmethylcycloalkanols of the general formula I in which
R¹ and R² are the same or different and represent hydrogen or C₁ to C₄ alkyl;
Y is C₁ to C₈ alkyl, phenyl, biphenyl, naphthyl, heteroaryl, benzyl, dioxolanyl or C₃ to C₈ cycloalkyl, each of these radicals being monosubstituted to triple by halogen, nitro, phenoxy, amino, C₁ to C₄alkyl , C₁ to C₄ alkoxy or C₁ to C₄ haloalkyl may be substituted;
X represents CH or N,
as well as their plant-compatible acid addition salts and metal complexes. 2. Azolylmethylcycloalkanols of general formula I according to claim 1, in the Y is optionally one to three times by fluorine or chlorine substituted phenyl radical. 3. Process for the preparation of azolylmethylcycloalkanols of the formula I. in which
R¹ and R² are the same or different and represent hydrogen or C₁ to C₄ alkyl;
Y is C₁ to C₈ alkyl, phenyl, biphenyl, naphthyl, heteroaryl, benzyl, dioxolanyl or C₃ to C₈ cycloalkyl, each of these radicals being monosubstituted to triple by halogen, nitro, phenoxy, amino, C₁ to C₄alkyl , C₁ to C₄ alkoxy or C₁ to C₄ haloalkyl may be substituted;
X represents CH or N,
as well as their plant-compatible acid addition salts and metal complexes, characterized in that a compound of formula II in which Y, R¹ and R² have the meanings given in Claim 1, with a compound of the general formula III in which Me represents a hydrogen atom or a metal atom and X denotes CH or N, and the compounds thus obtained are converted into their salts or into their metal complexes, if appropriate with acids which are tolerated by plants. 4. Compounds of the general formula II in the
Y is C₁ to C₈ alkyl, phenyl, biphenyl, naphthyl, heteroaryl, benzyl, dioxolanyl or C₃ to C₈ cycloalkyl, each of these radicals being monosubstituted to triple by halogen, nitro, phenoxy, amino, C₁ to C₄alkyl , C₁ to C₄ alkoxy or C₁ to C₄ haloalkyl may be substituted;
R¹ and R² are the same or different and are hydrogen or C₁ to C₄ alkyl. 5. Fungicidal composition comprising a carrier and a fungicidally effective amount of an azolylmethylcycloalkanol of the general formula I. in which
R¹ and R² are the same or different and represent hydrogen or C₁ to C₄ alkyl;
Y is C₁ to C₈ alkyl, phenyl, biphenyl, naphthyl, heteroaryl, benzyl, dioxolanyl or C₃ to C₈ cycloalkyl, each of these radicals being monosubstituted to triple by halogen, nitro, phenoxy, amino, C₁ to C₄alkyl , C₁ to C₄ alkoxy or C₁ to C₄ haloalkyl may be substituted;
X represents CH or N,
or its plant-compatible acid addition salt or its metal complex. 6. A method of combating fungi, characterized in that an fungicidally effective amount of an azolylmethylcycloalkanol of the general formula I in which
R¹ and R² are the same or different and represent hydrogen or C₁ to C₄ alkyl;
Y is C₁ to C₈ alkyl, phenyl, biphenyl, naphthyl, heteroaryl, benzyl, dioxolanyl or C₃ to C₈ cycloalkyl, each of these radicals being monosubstituted to triple by halogen, nitro, phenoxy, amino, C₁ to C₄alkyl , C₁ to C₄ alkoxy or C₁ to C₄ haloalkyl may be substituted;
X represents CH or N,
or whose plant-compatible acid addition salt or metal complex has an effect on fungi or on materials, areas, plants or seeds threatened by fungal attack. 7. Means for regulating plant growth, containing a carrier to a regulating effective amount of an azolylmethylcycloalkanol of the general formula I or its plant-compatible Acid addition salt or its metal complex according to claim 1. 8. Process for regulating plant growth, characterized in that that a regulatory effective amount of an azolylmethylcycloalkanol of the general formula I or its plant-compatible Acid addition salt or metal complex according to claim 1 Cultivated plants or their habitat can act.   9. A compound of formula I according to claim 1, in which R¹ and R² are hydrogen, Y is 4-chlorophenyl and X is N. 10. A compound of formula I according to claim 1, in which R¹ and R² are hydrogen, Y is 4-methylphenyl and X is N.