CA2032285A1

CA2032285A1 - Substituted azolylmethylcycloalkanols and fungicides containing them

Info

Publication number: CA2032285A1
Application number: CA002032285A
Authority: CA
Inventors: Rainer Seele; Bernhard Zipperer; Michael Keil; Norbert Goetz; Eberhard Ammermann; Gisela Lorenz; Reiner Kober; Thomas Kuekenhoehner; Albrecht Harreus; Wilhelm Rademacher
Original assignee: Individual
Current assignee: BASF SE
Priority date: 1989-12-16
Filing date: 1990-12-14
Publication date: 1991-06-17
Also published as: ES2085877T3; EP0433780B1; DK0433780T3; HU208612B; JPH03197464A; IL96681A0; AU652926B2; KR0163185B1; IL96681A; DE59010258D1; EP0433780A1; KR910011806A; AU6809390A; HU908283D0; ATE136301T1; GR3019879T3; HUT55956A

Abstract

O.Z. 0050/41291 Abstract of the Disclosure: Azolylmethylcycloalkanols of the general formula I

(I) where R1 and R5 are identical or different and are each hydrogen or alkyl;
R1 and R5 together are >CH=CH-R7 or >CH-Z-R7, where Z is CH2, O, S, SO, SO2 or N-R8;
R7 is alkyl, phenyl, biphenyl, naphthyl, heteroaryl, benzyl or cycloalkyl, where each of these radicals may be substituted, or is tetrahydropyranyl;
R2 and R3 are each hydrogen or alkyl, or, where R1 and R5 are >CH=CH-R7, R2 and R3 together may additionally be =CH-R7;
R4 and R6 are each hydrogen or alkyl, or R3 and R4 together with the carbon atoms on which they are substituents are a saturated or unsaturated 5-membered or 6-membered carbocyclic ring, or R2, R3, R4 and R9 together with the carbon atoms on which they are substituents are an unsubstituted or halogen-substituted phenyl ring, or where R1 and R5 are >C=CH-R7, R2 and R3 together may additionally be =CH-R7;
R8 and R9 to R12 are each hydrogen, alkyl, phenyl, bi-phenyl, naphthyl, heteroaryl, benzyl, dioxolanyl or cycloalkyl, where each of these radicals may be substituted;
T is (CH2)n, =CR11R12, O or S;
n is an integer from 1 to 5, with the proviso that R1 to O.Z. 0050/41291 R12 are not simultaneously hydrogen, and with the proviso that R1 and R5 together are not or

Description

O.Z. 0050/41291 ubstituted azolylmethy~.s~C~2~ ~-a~ols and funqicides containina them The present invention relates to novel azolyl-methylcycloalkanols of the seneral formula I

N~
I-X (I) R2~Rl R 4~ g T~ ~R 6 where R1 and R5 are identical or different and are each hydrogen or C1- to C4-alkyl;
Rl and Rs together with the carbon atom on which they are substi~uents are >C=CH-R7 or >CH-Z-R7, where Z is CH2, O, S, SO, SO2 or N-Ra;
R7 is Cl- to C8-alkyl, phenyl, biphenyl, naphthyl, hetero-aryl, benzyl or C3- to C8-cycloalkyl, where each of these radicals may be monosubstituted to trisubstituted by halogen, nitro, phenoxy, amino, Cl- to C4-alkyl, Cl- to C4-alkoxy or Cl- to C4-haloalkyl, or i9 tetrahydropyranyl, or, where R1 and R5 together with the carbon atom on which they are 3ubstituents are >CH Z-R7, R7 may additionally be hydrogen;
RZ and R3 are each hydrogen or Cl- to C4-alkyl, or, where R1 and R5 together with the carbon atom on which they are ~ubstituent~ are >C=CH-R7, R2 and R3 together with the carbon atom on which they are substituents may addition-ally be >CaCH-R7;
R4 and RA are each hydrogen or Cl- to C4 alkyl, or R3 and R4 togekher with the carbon atoms on which they are substituents are a saturated or unsaturated 5-membered or 6-membered carbocyclic riny, or R2, R3, R4 and R9 together with the carbon atoms on which they are sub~tituents are an unsubstituted or - 2~ 2 ~J ~ '~ O. Z . 0050/41291 halogen-substituted phenyl ring, or where Rl and R5 together with the carbon atom on which they are substituents are >C=CH-R7, R2 and R3 together with the carbon atom on which they are substituents may additionally be >C=CH-R7;
R6, R9 to Rl2 are each hydrogen, C~ to C~-alkyl, phenyl, biphenyl, naphthyl, heteroaryl, benzyl, dioxolanyl or C3-to Ca-cycloalkyl, where each of these radicals may be monosubstituted to trisubstituted by halogen, nitro, phenoxy, amino, Cl- to C4-alkyl, Cl- to C4-alkoxy or Cl- to C4-haloalkyl;
T is (CH2)n, =CR11Rl2, O or S;
n is an integer from 1 to 5, with the proviso that Rl to Rl2 are not sLmultaneously hydrogen, and with the proviso that Rl and R5 together are not =CH-CH2 ~ Cl or =CH-~CI

when R2 to R4 and R6 to Rl2 are hydrogen, and X is CH or N, and plant~tolerated acid addition salts and metal com-plexes thereof.
The present invention furthermore rela~es toprocesses for the preparation of these compounds, inter-mediates used, fungicidal and growth-regulating agents which contain the novel azolylmethylcycloalkanols as ~5 active substances, and methods for controlling fungi and methodY for regulating plant growth with the aid of these compounds.
European Patent 324,646 discloses azole-substitu~ed cycloalkanol derivativeR which carry a ,CH-CH 2~3c 1-group as the radical -Y-Rl, and their use as fungicides.
However, the fungicidal ac~ions are not sa~isfactory in all cases.
It i~ an object of the present invention to 2 2 ~ -~
~ 3 - o.z. 0050/41291 provide novel azole compounds having better fungicidal and growth-regulating actions.
We have found that this object is achieved by the azolylmethylcycloalkanols of the general formula I, defined at the outset, and plant-tolerated acid addition salts and metal complexes thereof.
We have furthermore found processes for the preparation of these compounds, intermediates used, fungicidal and growth-regulating agents which contain the novel azolylmethylcycloalkanols as active substances, and methods for controlling fungi and methods for regulating plant growth with the aid of these compounds.
The azolylmethylcycloalkanols of the general formula I are obtained in general in the form of racem-ates or as dia~tereomer mixtures. These isomers can beseparated in a conventional manner, for example on the basis of their solubility or that of their salts or by column chromatography, and can be isolated in pure form.
Pure enantiomers can be obtained from such an isolated diastereomer by known methods.
Both the individual dia~tereomers or enantiomers and mixture3 thereof generally obtained in the ~ynthesis can be used as fungicidal active ingredients.
With regard to the fungicidal action, compounds I in which R1 and R5 together with the carbon atom on which they are substituent~ are >C=CH- are particularly preferred.
If R1 and R5 together with the carbon atom on which they are substituents are >CH-Z-, preferred com-pound~ are thos2 in which Z is O or S.
Where R1 and R5 together with the carbon atom onwhich they are ~ubstituen~s are >C=CH- ~7 is bonded to the CH group; if Rl and R5 togethex with the carbon atom on which they are subR~ituents are >CH-Z-, there 1~ a bond between R7 and Z.
Example-~ of each radical are:
Cl-C8-alkyl, preferably Cl-C4-alkyl, in particular methyl, 2 ,.~
- 4 - O.Z. 0050/41291 ethyl, n-propyl, isopropyl, n-butyl sec-butyl or tert-butyl; among the Cl-C8-alkyl radicals of more than 4 carbon atoms, n-pentyl and neopentyl are preferred;
phenyl and halogen-substituted phenyl, ~uch as 2-chloro-phenyl, 3-chlorophenyl, 4-chlorophenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-bromophenyl, 3-bromo-phenyl, 4-bromophenyl, 2,3-dichlorophenyl, 2,4-dichloro-phenyl, 2,5-dichlorophenyl, 2,6-dichlorophenyl, 2-chloro-4-fluorophenyl or 2-chloro-6-fluorophenyl;
phenyl which is monosubstituted by nitro, phenoxy, amino or C1-C4-alkyl, such as 3-nitrophenyl, 4-nitrophenyl, 3-phenoxyphenyl, 4-phenoxyphenyl, 3-aminophenyl, 4-amino-phenyl, 4-ethylphenyl, 4-isopropylphenyl or 4-tert-butylphenyl;
phenyl which is substituted by two or three different radicals from among those mentioned above, eg. 2-chloro-6-methylphenyl;
phenyl which is monosubstituted or disubstituted by C1-C4-alkoxy, such as 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 4-tert-butoxyphenyl, 2,4-dimethoxyphenyl or 3,4-dimethoxyphenyl;
methylphenyl which is trisub~tituted by halogen, such as 2-trifluoromethylphenyl, 3-trifluoromethylphenyl or 4-trifluoromethylphenyl;
p-biphenyl;
1-naphthyl or 2-naphthyl;
hetaryl having 5 or 6 ring atoms, in particular 6-membered rings having up to three nitrogen atoms, such as 2-pyridyl, 3-pyridyl or 4-pyridyl, and 5-membered rings preferably having one or two of the hetero atoms O, S and N, in particular 2-furyl, 2-thienyl, 3-thienyl, 4-oxazolyl, 4-thiazolyl, 4-i50xazolyl, 5-isoxa~olyl or 5-imidazolyl;
benzyl; halobenæyl;
C3_CB_CYC10a1kY1, preferably cyclopantyl or cyclohexyl.
Wh~re R1 and R5 together with the carbon atom on which they are sub~tituents are >CH Z--, the novel ~J ~ ~J 2 ~ 3 !~

- 5 - o.z. 0050/41291 compounds of the general formula I in which R7 is hydrogen are al~o preferred.
Nhere Rl and Rs together with the carbon atom on which they are substituents are >C=CH-, the compounds in which R7 is 4-tetrahydropyranyl are also preferred.
R2 and R3 independently of one another may be identical or different and are each preferably hydrogen or n-alkyl of 1 to 4 carbon atoms, in particular methyl.
Where Rl and R5 together with the carbon atom on which they are substituents are >CH-Z-, the novel compounds I
in which R2 and R3 are identical are preferred. If Rl and R2 together with the carbon atom on which they are substi-tuents are >C=CH-, the azolylmethylcycloalkanols I in which R2 and R3 together with the carbon atom on which they are substituents form >C=CH-R7 are particularly noteworthy. For example, the radicals stated for R7 are then applicable, preferably tert-butyl, phenyl, 2-chloro-phenyl, 4-chlorophenyl, 4-fluorophenyl, 2~bromophenyl, 4-bromophenyl, 2,4-dichlorophenyl, 2-methylphenyl, 4-methylphenyl, 2-methoxyphenyl, 4-methoxyphenyl, 2-triflu-oromethylphenyl, 4-trifluoromethylphenyl, 2-furyl, cyclopentyl or cyclohexyl.
Suitable acid addition salts are the plant-tolerated salts of acids which do not adversely affect the ~ungicidal action of I, eg. the hydrochloride~, bromides, sulfate~, nitrate~, pho~phates, oxalates and dodecylbenzenesulfonate~. However, since the activity of the 8alts i~ due to the cation, the anion i~ not in general important. The novel active ingredient sal~s are ad~antageously prepared by reacting the azolylmethyl-cycloalkanols I with suitable acids.
Metal complexe~ of the novel compounds I or of their salts are preferably formed with metals of main group II, such as magnesium or calcium, of main groups III or IV, such a~ aluminum, tin or lead, or with me~als of subgroup~ I to VIII, the subgroup elements of the fourth period being par~icularly p~eferred, especially 2~ o Z. 0050/41291 copper, zinc, manganese, iron, cobalt and nickel. For this purpo~e, the azolylmethylcycloalkanols are reacted with the corresponding metal ~alts.
Preferred azolylmethylcycloalkanols are those of the general formula N
~N--X

~C~
where R1 and R5 together with the carbon atom on which they are substituents are >C=CH-R7 or ~CH-Z-R7, where ~ is O, S, S ~ S2 or N-R7;
R7 is C~- ~o C8-alkyl, phenyl, biphenyl, naphthyl, hetero-aryl, benzyl or C3- to C8-cycloalkyl, where each of these radicals may be monosubstituted to trisubstituted by halogen, nitro, phenoxy, amino, Cl- to C4-alkyl, C,- to C4-alkoxy or C,- to C4-haloal~yl, or is tetrahydropyranyl, or, where R1 and R5 together with the carbon atom on which they are substituents are >CH-Z-, R7 may additionally be hydrogen, RZ and R3 are each hydrogen or C,- to C4-alkyl, or, wher~
R1 and R5 together with the carbon atom on which they are substituents are >C=CH-, R2 and R3 together with the carbon atom on which they are substituent~ may addition-ally b0 >C=CH~R7;
n is an integer from 2 to 5~ and ~ is CH or N, and plant-tolerated acid addition salt3 and metal com-plexes thereof.
A~olylethanol derivatives of the general formula I

- 7 - O.Z. 0050/41291 ~11 N~N
CH2 (I) R 23~R I
R4 T~CH2 where R1 and R5 together with the carbon atom on which they are substituents are >C=CH-R7 or >C~-CH2-R7;
R7 is Cl~C~-alkyl, phenyl, biphenyl, naphthyl, heteroaryl, benzyl or C~-C8-cycloalkyl, where each of these radicals may be monosubstituted to trisubstituted by halogen, nitro, phenoxy, amino, Cl-C4~alkyl or Cl-C4-haloalkyl;
R2, R3 and R4 are identical or different and are each hydrogen or Cl- to C4-alkyl, or 10 R3 and R4 together with the carbon atoms on which they are substituents are a saturated or un~aturated 5-membered or 6-membered carbocyclic ring, or R2, R3 and R4 together with the carbon atoms on which they are substituents are an unsubstituted or halogen-substituted phenyl ring, orwhere R1 and R5 together with the carbon atom on which they are sub~tituents are >C=CH-R7-, R2 and R3 together with the carbon atom on which they are substituents may additionally be >C=CH-R7;
T is CH2, O or S, and X is CH or N, and plant-tol~rated acid addition salts and metal com-plexes thereof are also preferred.
Other preferred azolylmethylcycloalkanols are tho~e of the general formula I
N~X
N~

~R 6 where Rl and R5 are identical or dif~erent and are each hydrogen :;
;

_h~ 3 ?~ ~J ~ ~3 O. Z . 005n/4l29l or Cl- to C4-alkyl;
R6 i5 Cl- to C8-alkyl, phenyl, biphenyl, naphthyl, hetero-aryl, benzyl, dioxolanyl or C3- to Ca-cycloalkyl, where each of the~e radicals may be monosubstituted to trisub-stituted by halogen, nitro, phenoxy, amino, Cl- to C4-alkyl, Cl- to C4-alkoxy or Cl~ to C4-haloalkyl, and X is CH or N, and plant-tolerated acid addition salts and metal com-plexes thereof.
10Azolylmethylcyclohexanols of the general formula I ~x~
N~ ~ ,R 7 R 9~R I O

where Y is > C=CH- or ~ CH-CHz-;
15R4 and R9 to R12 are each hydrogen, Cl- to C8-alkyl, C3- to C6-cycloalXyl or phenyl, where each of these radicals may be monosubstituted to trisubstituted by halogen, nitro, phenoxy, amino, Cl- to C~-alkyl, Cl- to C4-alkoxy or Cl- to C4-haloalkyl, with the proviso that R4 and R9 to Rl2 are not simultaneously hydrogen;
R7 is Cl- to C9~alkyl, phenyl, biphenyl, naphthyl, hetero-aryl, benzyl or C3-to C8-cycloalkyl, where each of these radicals may be monosubstituted to trisubstituted by halogen, nitro, phenoxy, amino, Cl- to C4-alkoxy or Cl- to C4 haloalkyl, and X is CH or N, and plant-tolerated acid addition salts and metal com-plexes thereof are also preferred.
Compounds of the general formula I where T is CH2 and R4 and R9 have the abovemen~ioned meanings, with the proviso that R4 and R9 are not both simul~aneously hydro-gen and the remaining radic~ls have ~he abovementioned meanings are also preferred.
The novel azolymethylcycloalkanols I are C~ ~ 3 2 h ~ ~
- 9 - O.Z. 0050/41291 generally prepared ~y reacting a compound of the general formula II with a compound of the general formula III.
Preferred compounds III are those in which ~e is hydrogen or an alkali metal atomr in particular sodium or S potas s iUlTl .
If Me is hydrogen, a weight ratio of III to II of from 2 : 1 to 6 : 1, in particular about 3 : 1, is advantageously maintained. The reaction is carried out in the presence or absence of an inert solvent or dilu-ent, advantageou~ly with the addition of an inorganic or organic base and with or without the addition of a reaction accelerator.
The preferred solvents and diluents include ketones, such as acetone, methyl ethyl ketone or cyclo-hexanone, nitriles, such as acetonitrile or propio-nitrile, alcohols, 4uch as methanol, ethanol, isopropan-ol, n-butanol or glycol, esters, such as ethyl acetate, methyl acetate or butyl acetate, ethers, such as tetra-hydrofuran, 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 use~ as acid acceptors in the reaction are, for ex~mple, alkali metal hydroxides, ~uch as lithium hydroxide, sodium hydroxide or potassium hydroxide, alkali metal carbonates, such as sodium carbonate, potassium carbonate, sodium bicarbonate or potassium bicarbonate, pyridine or 4-dimethylamino-pyridine. Howe~er, it is also possible to use other conventional bases.
Preferred reaction accelerators are metal hal-ides, such as sodium iodide or potassium iodide, quater-nary ammonium salts, such as tetrabutylammonium chloride, bromide or iodide, or crown ethers, such as 12-crown-4, 15-crown~5, 18-crown-6 or dicyclohexano-18-crown-6.
The reaction is generally carried out at from 10 to 150C, in particular from 20 to 120C, under :

'~ :

~ ~ ~ rJ 2 ~ o.Z. 0050/41291 atmospheric or ~uperatmo~pheric pressure, continuously or batchwise.
If Me is a metal atom, a weight ratio of III to II of from 1 : 1 to 3 : 1, in particular 1 : 1, is preferred. The reaction is carried out in the presence or absence of a solvent or diluent and with or without the addition of an inorganic or organic base. The preferred solvents and diluents include amides, such as dimethylformamide, diethylformamide, dLmethylacetamide, N-methylpyrrolidone, hexamethylphosphorotriamide, sul-foxides, such as dimethyl sulfoxide, and finally sulfolane.
Suitable bases, which may also be used as acid acceptors in the reaction are, for example, alkali metal hydrides, such as lithium hydride, sodium hydride and potassium hydride, alkali metal amide~, such as sodium amide and potassium amide, and sodium tert-butylate and potassium tert-butylate.
The reaction is carried out in general at from -10 to 120C, preferably from 20 to 80. In the presence of a solven~, the reaction is advan~ageously carried out at the boiling p~int of the particular solvent.
The compounds II can be prepared in a simple manner by known method~ from the ketones of the formula IV
Il (IV~
R 9~T R 10 for example by reaction with trime~hylsulfonium methyl-sulfate (cf. Corey and Chaykov~ky, J. Am. ChemO Soc. 64 (1962), 3782).
The compounds IV can be prepared by generally known methods. Where Rl and R5 form >CH-Z-, Can~acuzene and Tordeux, Can. J. Chem. 54 (17) (1976), 2659-2766 may be mentioned; if Rl and R5 form >C=CH-, reference may be madP to Houben-Weyl-Nuller, Method~n der organischen ~ J3~ $ ~ O.Z. 0050/41291 Chemie, Georg-Thieme Yerlag, Stuttgart 1972, Vol. Vlb.
Examples of the compounds I~ are shown in Tables 1 and 2.
The compounds of general formula I and their salts and metal complexes are suitable as fungicides and are well tolerated by plant~.
Preparation Examples Method A1:
2-(4-Chlorophenoxy)-cyclohexanone ~CI

23.3 g (0.181 mol) of 4-chlorophenol were added to a solution of 5.4 g (0.225 mol) of sodium hydride (50~
strength dispersion in mineral oil) in 100 ml of N,N-dimethylformamide. Thereafter, 20 g (0.151 mol) of 2-chlorocyclohexanone were added and stirring was carried out for 24 hours at room temperature. After the addition of 100 ml of water and extraction several times with methyl tert-butyl ether, the organic phase was washed with water, dried over sodium sulfate and evaporated down under reduced pressure.
Yield: 32.9 g (97~) Melting point: 102-104C.
Method Bl:
3-(4-Chlorophenoxy)-l-oxabicyclo~ n .2.5]octane ~CI
22.7 g (0.121 mol) of trime~hylsulfonium methyl-sulfat~ and 30 g of concentrated sodium hydroxide ~olu-tion were added to a solution of 12.3 g (0.055 mol) of 2-(4-chlorophenoxy)-cyclohexanone in 100 ml of methylene chloride. After the reaction mix~ure had been stirred for from 12 to lS hours at room ~emperature (20C), 100 ml ~ 1~ ? ~ ~ 3 0 z. 0050/41291 of water were added to ~he solution and the organic phase was separated off, washed twice with water, dried over sodium sulfate and evaporated down.
Yield: ll.S g (88%) S Method B2:
3-(4-chlorobenzylidene)-l-oxabicycloEo.2.s]octane o~7 ~cl The procedure d~scri~ed in Method B1 was fol-lowed, 23.5 g (0.108 mol) of 2-(4-chlorobenzylidene)-cyclohexanone in 100 ml of methylene chloride, 24 g (0.128 mol) of trimethylsulfoni~un methyl~ulfate and 50 ml of 50% strength by weight sodium hydroxide solution being used.
Yield: 24 g (95%) 1-(1,2,4-Triazol-l-ylmethyl)-2-(~-chlorophenoxy)-cyclo-hexan-l-ol ~N~
N~ --¦
~CI

3.4 g of 50% strength by weight sodium hydroxide solution were added to a solution of 3.5 g ~0.051 mol) of 1,2,4-tria201e in 50 ml of N,N-dlmethylformamiAe and the mixture was heated at 50C for 30 minutes. Thereafter, .0 g (0.033 mol) of 3-t4-chloropheno~y)-1-oxabicyclo-[0.2.5]octane, which had been dissolved in 20 ml of N~N
dimethylfonmamide, were added dropwi~e at room tempera-ture. After the reaction mix~ure had been s~irred for 15 hours at room temperature, 100 ml of water were added to the solution and the mixture was extracted se~eral tLmes by shaking with methyl tert-butyl ether. The isolated organic phase was washed twice with water~ then dried ~3 ~ 3O.z. 0050/41291 over sodium sulfate and evaporated down. Crystallization of the residue from methyl tert-butyl ether/n-hexane gave the product as a 2 : 1 diastereomer mixture.
Yield: 6.5 g (63~) Melting point: 120-122C

--r4 - O.Z. 0050/41291 1-tl,2,4-Triazol-l-ylmethyl)-2-(4-chlorophenylidene)-cyclohexan-l-ol N~
N
~CI

6.8 g of 50~ strength by weight sodium hydroxide solution were added to a solution of 6.2 g (0.091 mol) of 1,2,4-triazole in 100 ml of N,N-dimethylformamide and the mixture was heated for 30 minutes at 50C, similarly to Example 1. After the reaction mixture had been cooled to room temperature, lO.S g (0.045 mol) of 3-(4-chloro-benzylidene)-1-oxabicyclo[0.2.5]octane, which had been dissolved in 50 ml of N,N-dimethylformamide, were added dropwise to the solution and the mixture was stirred for 12 hours at room temperature. Thereafter, 100 ml of water were added, the mixture was extrac~ed several times with methyl tert butyl ether and the organic phase was washed with water, dried over sodium sulfate and evapora-ted down under reduced pressure.
Yield: 10.5 g (77%).
The compounds listed in Tables 1 and 2 can be prepared according to ~ethods B1 and B2, and those in Tables 3 and 4 can be prepared according to Examples 1 and 2.

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~ 50 ~~ s~ ~ ~-Z 0050/41291 Method B3 2-(4-Chlorobenzylidene)-spiro-(trans-decalin-1,2-oxirane (compound No . 5 .1 ) ~CI
4 5 . 5 g of (O.24 mol) of trimethyl 8Ul fonium methylsulfate and 42 ml of concentrated sodium hydroxide solution were added to a solution of 30.2 g (0.11 mol) of 2-(4-chloro-benzylidene)decal-l-one in 200 ml of methylene chloride.
After the reaction mixture has been stirred at room temperature (20C) for 12 hours, 100 ml of water were added to the solution and the organic phase was separated off. The organic phase was washed twice with water and dried over sodium sulfate and evaporated down.
Yield: 29 g (91 ~
Melting point: 102-105C

1-(1,2,4-Triazol-l-ylmethyl)-2-(4-chlorobenzylidene)-decan-1-ol (compound No. 8.1) ~7 N~N~
~CI
5.2 ml of 50 % strength by weight sodium hydroxide solution were added to a qolution o 6.~ g (0.1 mol~ 1,2,4-triazole in 50 ml of N,N-dLmethyl-formamide and the mixture was heated at 50C for 30 minutes. 14.4 g of (o.os mol~ of 2-(4-chlorobenzylidene)-spiro(~rans-decalin-1,2-oxirane), which had been dis-solved in 30 ml of N,N-dime~hylformamida, were then added dropwise at room temperature. After the reaction mixture had ~een stirred at room temperature for 15 hours, 100 ml of water were added ~o the solution, which was extracted several times when shaken with methyl ter~-butyl ether.
The isolated organic phase was washed twice with water and then dried over sodium sulfate and evaporated down.

- 51 - O.Z. 0050/41291 3J ~J 3 ~' By crystallizing the residue from methyl tert-butyl ether/n-hexane, the product was obtained as an enantiomer mixture.
Yield: 13.3 g (63 ~) Melting point: 180-186C
The compounds listed in Tables 5, 6 and 7 can be prepared according to B3 and the compounds in Tables 8, 9 and 10 can be prepared according to Example 3.

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- 82 ~ ~ ,$ ~ O.Z. 0050/41291 Method B4 4-(4-Chlorophenyl)-l-oxabicyclo[0.2.5]octane (compound No.1, Table 1) O

Cl 54.4 g (0.30 mol) of trimethylsulfonium methylsulfate and 50 ml of 50 % strength of sodium hydroxide solution were added to a solution of 30 g (0.14 mol) of 3-(4-chloro-phenyl)cyclohexanone in 100 ml of methylene chloride.
After the reaction mixture had been stirred for 12 hours at room temperature (20C), 100 ml of water were added to the solution and the organic phase was separated off. The organic phase was washed twice with water, dried over sodium sulfate and evaporated down.
Yield: 28.2 g (91 %) 1-(1,2,4-Triazol-l-yl-methyl)-3-(4-chlorophenyl)-cyclo-hexan-1-ol (compound No. 12.1, Table 12) F~
N~N~

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12.4 g of S0 % strength by weight sodium hy-droxide solution were added to a solution of 11.3 g (0~16 mol) of triazole in 100 ml of N,N-dimethylformamide and the mixture was heated at 50~C for 30 minutes. 18.2 g of (0.08 mol) of 4-(4-chlorophenyl~ oxabicyclo-~0.2.5]octane, which had been di~olved in 20 ml of N,N-dimethylformamide, w~re addad dropwise at room tempera-ture. After the reaction mixture had been stirred at room temperature for 15 hours, 100 ml of water were added to the solution~ which was extrac~ed several ~imes by shaking with methyl tert-bu~yl ether. The organic phase was washed ~wice with water and dried over sodium sulfate ; <..v' rld f~J ~ o Z 0 0 5 0 / 412 91 and evaporated down.
Crystallization of the residue from methyl tert-butyl ether/n-hexane gave the product as a 2:1 diastereomer mixture.
Yield: 20.3 g (87 %) Melting point: 128-130C
The compounds listed in Table 11 can be prepared according to Method B4 and the compounds listed in Table 12 according to Example 4.

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- 91 - ~.Z. 0050/41291 ~ ~ ~ 3 2 2 g ~3 Method A2 ^~
2-(4-Chlorobenzylidene)-3,5,5-trimethylcyclohexanone H 3C ~=`C 1 10 g of boron trioxide were added to a solution of 763 g of (5.45 mol) of 3,3,5-trimethylcyclohexanone and 140.5 g (1 mol) of 4-chlorobenzaldehyde, and water was separaked off at a reaction temperature of 190C over 5 hours. In a subsequent distillation of the reaction mixture, 181 g (69 ~) of 2-(4-chlorobenzylidene)-3,5,5-trimethylcyclohexanone were obtained at 0.2 mbar and 168~.
Method B5 3-~4-Chlorobenzylidene)-4,6,6-trimethyl-1-oxabicyclo-~0.2.5]octane O

H 3C~C 1 63 g (0.335 mol) of trimethylsulfonium methylsul-fate and 70 g of concentrated sodium hydroxide solution were added to a solution of 40 g (0.15 mol) of 2-(4-chlorobenzylidene)-3,5,5-trimethylcyclohexanone in 200 ml of methylene chloride. After the reaction mixture had been stirred at room temperature (20C) for from 12 to lS
hours, 200 ml of water were added to the solution and the organic phase was separated off. The organic pha e was washed twice with water, dried over sodium sulfate and evaporated down.
Yield: 37.4 g (89 %) 1-(1,2,4-Triazol-l-yl-methyl)-2 (4-chlorobenzylidene)-3,5,5-trimethylcyclohexan-1-ol ~x~
N~N~
H3C~Cl ~ 2t ~ 2 ~ ~ 3 Z~ 0050/41291 9.8 g of 50 ~ strPngth by weight sodium hydroxide solu-tion were added to a solution of 8.8 g (0.128 mol) of 1,2,4-triazole in 100 ml of N,N-dimethylformamide and the mixture was heated at 50C for 30 minutes. 27.1 g (0.098 mol) of 3-(4-chlorobenzylidene~-4,6,6-trLmethyl-1-oxabicyclo[0.2.5)octane, which had been dissolved in 50 ml of N,N-dimethylformamide, were then added dropwise at room temperature (20C) and the mixture was stirred for 12 hours at room temperature. Thereafter, 200 ml of water were added, the mixture was extracted several times with methyl tert-butyl ether and the organic phase was washed with water, dried over sodium sulfate and evapor-ated down under reduced pressure.
Yield: 4.0 g (12 %) Melting point: 88-90~C
The compounds listed in Table 13 can be prepared according to Method B5 and the compounds listed in Table 14 according to Example 5.

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_. S C,~ S S ~: S

_ C S T T T T ~ S

_ ~S T T r S r T T

~t ll T S S T T X 1 V ~
T T ~r r S ~ ~ x _ ~ ~ ~ ~ ~ I` a~ o~ o X ,~

~ J2~
The azolylmethylcycloalkanols have excellent activit~ against a broad spectrum of phytopathogenic fungi, in particular from the class consisting of the Ascomycetes and Basidomycetes. Some of them have sys-temic activity and can be used as foliage and soil fungicides.
They are particularly important for controlling a multiplicity of fungi on various crops, such as wheat, rye, barley, oats, rice, corn, grass, cotton, soybean, coffee, sugar cane, grapevines, fruit and ornamental plants and vegetable plants such as cucumber, beans and cucurbitaceae, and on the seeds of these plants.
They are specially suitable for controlling the following plant diseases:
Erysiphe graminis (powdery mildew) in cereals, Erysiphe cichoracearum and Sphaerotheca fuliginea on cucurbitaceae, Podosphaera leucotricha on apples, Uncinula necator on grapevines, Puccinia species on cereals, Rhizoctonia species on cotton and lawns, Ustilaso 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 and grape-vines, Cerco~pora axachidicola on peanuts, Pseudocercosporella herpotrichoides on wheat and barley, ~0 Pyricularia oryzae on rice, Phytophthora infestans on potatoes and tomatoes, Fusarium and Verticillium species on various plants, Plasmopara viticola on grapevines and Alternaria species on vegetables and fruit.
The compounds are used by spraying or dusting the plants with the active ingredients or treating the sePds of the plants with the active ingredients. Application - 104 ~ ~ Z 0050/41291 tJ .~
is effected before or after infection of the plants or seeds by the fungi.
They can be converted into the conventional formulations, such as solutions, emulsions, suspensions, dusts, powders, pastes and granules. The application forms depend on the intended uses; they should in any case en~ure fine and uniform distribution of the azolyl-methylcycloalkanol. The formulations are prepared in a known manner, for example by extending the active in-gredient with solvents and/or carriers, if desired withthe use of emulsifiers and dispersants, and other organic solvents may also be used as auxiliary solvents when water is used as a diluent. Suitable assistants for this purposs are essentially: solvents, such as aromatics (eg.
xylene), chlorinated aromatics (eg. chlorobenzenes), paraffins (eg. mineral oil fractions), alcohols (eg.
methanol and butanol), ketones (eg. cyclohexanone), amines (eg. ethanolamine and dimethylformamide) and water; carriers such as ground natural minerals (eg.
kaolins, aluminas, talc and chalk) and ground synthetic minerals ~eg. finely divided silica and silicates);
emulsifiers, such as nonionic and anionic emulsifiers (eg~ polyoxyethylene fatty alcohol ethers, alkyl-sulfonates and arylsulfonates) and dispersants, such as ligninsulfite waste liquors and methylcellulose.
The fungicides contain in general from 0.1 to 95, preferably from 0.5 to gO, % by weight of active ingredients.
The application rates are from 0.02 to 3 kg of active ingredient per ha, depending on the type of effect desired. The novel compounds can also be used in mater-ial protection (wood preservation), for example against Paecilomyces variotii.
The agents and the ready-to-use formulations prepared therefromt such a~ solutions, emul~ions, suRpen-sions, powders, dusts, pastes or granules, are used in a known manner, for example by spraying, atomi~ing, - 152 ~J3 ~ f'J ~ ~ 3 O.Z. 0050/41291 dusting, broadcasting, dressing or pouring.
Examples of such formulation~ are:
I. a solution of 90 parts by weight of compound No.
3.1 or 4.1 and 10 parts by weight of N-methyl-~-S pyrrolidone, which is suitable for use in the form of very small drops;
II. a mixture of 20 parts by weight of compound No.
3.2, 80 parts by weight of xylene, 10 parts by weight of the adduct of from 3 to 10 moles of ethylene oxide with l mole of oleic acid N-monoethanolamide, 5 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 5 parts by weight of the adduct of 40 moles of ethylene oxide with 1 mole or castor oil; by finely distributing the solution in water, a-dispersion is obtained;
III. an aqueous disper~ion of 20 parts by weight of compound No. 3.84, 40 parts by weight of cyclo-hexanone, 30 parts by weight of isobutanol and 20 parts by weight of the adduct of 40 moles of ethylene oxide with l mole of castor oil;
IV. an aqueous dispersion of ~0 parts by weight of compound No. 3.85~ 25 parts by weight of cyclo-hexanol, 65 parts by weight of a mineral oil 2.S fraction boiling within a range from 210 to 280C
and 10 parts by weight of the adduct of 40 moles of ethylene oxide with 1 mole of castor oil;
V. a mixture milled in a hammer mill consi~ting of 80 parts by weight of compound No. 3.8S, 3 parts by weight of the sodium salt of diisobutyl-naphthalene-~-sulfonic acid, 10 parts by weight of the sodium salt of a lignin~ulfonic acid obtained from a ~ulfite waste liquor and 7 parts by wPight of silica gel powder; by finely di~
tributing the mixture in water, a spray liquor is ob~ained;
VI. A thorough mixture of 3 parts by weight of ~P~ 2 ~ 3 o . z . 0050/41291 compound No. 3 . 90 and 97 parts b~ weight of finely divided kaol in; this dusting agent con-tains 3% by weight of ac~ive ingredient;
VII. a thorough mixture of 30 parts by weight of compound No. 4.2, 92 parts by weight of silica gel powder and 8 parts by weight of liquid paraffin, which has been sprayed onto the ~urface of the silica gel; this formulation Lmparts good adhesion to the active ingredient;
VIII. a stable aqueous dispersion of 40 parts by weight of compound No. 4.7, 10 parts by weight of the sodium salt of a phenolsulfonic acid/urea/formal-dehyde condensate, 2 parts by weight of silica gel, 4 8 parts by weight of water, which can be lS further diluted, IX. a stable oily dispersion of 20 parts by weight of compound No. 4. 8, 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of a fatty alcohol polyglycol ether, 20 parts by weight of the sodium salt of a phenolsulfonic acid/urea/formaldehyde conden-sate and 6 8 parts by weight of a paraffinic mineral oil.
The novel agents may also be present in these application forms together with other active ingredients, for example with herbicides, insecticides, growth regula-tor~ or fungicides, or with fertilizers.
The ~zolylmethylcycloalkanols of the formula I
can influence virtually all developmen~ s~age~ of the plant in various ways and are therefore used as growth regulator~. The variety of actions of the plant grow~h regulators depends in particular a) on the plant species and variety, b) on the time of application, based on the development stage of the plant, ~nd on the season, c) on the place and method of application (seed dress-ing, soil treatment or foliage application), :, - 10 7 ~r u ~d 2 ?A ~ ~ o . z . 0050/41291 d) on climatic factors, for example temperature and amount of precipitation, and also on the length of day and light intensity, e) on the soil characteristic~ (including fertilizer application), f) on the formulation or application form of the active ingredient and finally g) on the concentrations in which the active substance is u~ed.
From the number of different possible methods of application of the novel plant growth regulators in cultivation, some are mentioned below.
A. The compounds which can be used according to the invention can be employed for pronounced inhibition of the vegetative growth of the plants, which manifests itself in particular in a reduction in the length of growth. The treated plants accordingly exhibit squat growth; furthermore, a dull foliage coloration is observed.
A practical advantage is, for example, the reduction in the growth of grass along road edges, hedge~, canal banks and on lawn areas, such as parks, sports complexes, orchards, ornamental lawns anA air-fields, so that the labor-int~nsive and ~xpensive cutting of grass can be reduced.
The increase in the strength of crop3 susceptible to lodging, such as sereals, corn, rice, sunflowers and soyb~an, i8 also of economic interest. The re~ulting shortening and strengthening of th~ stem reduce or eliminate the danger of lodging (bending) of plants under unfavorable weather conditions prior to harvesting.
The use of growth regulator~ for inhibiting the length of growth and for altering the period of ripening of cotton is also important. ~his permits complately mechanized harvesting of thi~ impor~ant crop.
By u~ing yrowth regulators, it is also possible to increase or inhibit lateral branching of the plants.

1 O 8f '~t 5 ; ,~ r ~ t O z 0 0 5 0 / D~ 1 2 9 1 This is of interest when, for example in the case of ~obacco plants, the formation of side shoots is to be inhibited in favor of leaf growth.
Growth regulators can also be used to achieve a considerable increase in the frost resistance, for example in the case of winter rape. On the one hand, the length of growth and development of a leaf or plant mass which is too luxuriant (and hence particularly suscep-tible to frost) are inhibited. On the other hand, the young rape plants are inhibited in the vegetative stage of development after sowing and prior to the onset of the winter frosts, despite favorable growth conditions. This also eliminates the frost risk of such plants, which tend to exhibit premature cessation of the inhibition o blooming and a transition to the generative phase. In other crops too, for example winter cereals, it is advantageous if, by treatment with novel compounds in the fall, the stocks are well tillered but do not ~tart the winter with too luxuriant a growth. This makes it possible to prevent increased sensitivity to frost and, owing to the relatively small leaf or plant mass, attack by various diseases tfor ex~mple fungal diseases). The inhibition of vegetative growth also permits denser planting of the soil in many crops, so that a higher yield, based on the soil area, can be achieved.
B. The novel agent~ can be used to achieve higher yields bo~h of plant parts and of plant ingredients. For example, it i~ po3sible to induce the growth of larger amounts of buds, blooms, leaves, fruits, seeds, roots and tubers, to increa e the content of sugar in sugar beet, sugar cane and citrus fruits and the protein content in cereals or soybean or to stimulate rubber trees to produce greater latex flow.
The azolylmethylcycloalkanols of the formula I
can result in increased yi~lds through intervention in the plant metabolism or by promotion or inhibition of the vegetative and/or of the generative growth.

~ ~ ~ 2 ,~
- 109 - O.Z. 0050/41291 C. Finally, plant growth regulators can be used to achieve both a shortening or lengthening of the stages of development and an acceleration or retardation of the ripening of the harvested plant parts before or after harvesting.
For example, facilitating harvesting is of economic interest, this being permitted by concentrated dropping or a reduction in the adhesion to the tree in the case of citrus fruits, olives or other types and varieties of pomes, drupes and hard-shelled fruit. The same mechanism, ie. the promotion of ~he formation of abscission tissue between the fruit or leaf part and the shoot part of the plant is also essentia~ for readily controllable defoliation of crops.
D. Growth regulators may furthermore be used to reduce the water con~umption of plants. This is par-ticularly Lmporkant for agricultural areas which have to be artificially irrigated at great expense, for example in arid or semiarid regions. By using the novel substances, it is possible to reduce the intensity of irrigation and hence to carry out more economical farm-ing. The influence of growth regulators results in better utilization of the available water, because, inter alia, the extent of opening of the ~tomata is reduced, a thicker epidermis and cuticula are formed, the root penetration of the soil is improved and the microclimate in the stock of plants is advantageously affected by more compact grow~h.
The active ingredients to be used according to the invention can be fed to the crops both via the seed (as a seed dressing) and via the soil, ie. through the roots or via the foliage.
Because of the high toleration by plants, thP
application rate can be greatly varied~
In the ca~e of seed treatment, in general amounts of active ingredien~ of from 0.001 to 50, preferably from S ;'~J ' 1 & ~j - 110 - O.Z. 0050/~1291 0.01 to 10, g per kilogram of seed are required.
For foliage and soil treatment, in general doses of from 0.01 to 10, preferably from O.OS to 3, kg/ha are regarded as sufXicient.
The formulations or the ready-to-use preparations produced therefrom, such as solutions, emulsions, suspen-sions, powders, dusts, pastes or granules, are applied in a known manner, for example by the preemergence method or the postemergence method or as dressings.
Use Examples The comparative active ingredient chosen was 1-(1,2,4-triazol-1-ylmethyl)-2-~4-chlorobenzyl)-cyclo-hexan-l-ol, which is disclosed in European Patent 324,646.
EXAMPLE I
Activity against Pyrenophora teres Barley seedlings of the Igri variety, in the two-leaf stage, were sprayed to run-off with the aqueous suspensions which contained 80~ of active ingredient and 20% of emulsifier, the percentages being based on dry substance. After 24 hours, the plants were inoculated with a spore suspension of the fungus Pyrenophora tere~
and placed for 48 hour~ in an air-conditioned chamber with high atmospheric humidity at 18~C. Thereafter, the plar.ts were cultivated in a greenhouse at from 20 to 22C
and 70% relative humidity for a further 5 days. The extent of development of the symptoms was then determined.

s~ ?
~ ~ '.,' I f t`l f J l_ J
~ O.Z. 0050/41291 Rating: Infested leaf area in %
Active ingredient Infestation of the leaves after from Example application of 0.05% strength aqueous active ingredient formulation Ratings ~ ~ infestation 3.90 0 0 4.1 l 5 4.7 1 5 4.8 1 5 Comparative active ingredient 3 25 Untreated 4-5 65 EXAME'LE II
Activity against cucumber mildew Young cucumber plants of the Chinesische Schlange variety, in the two-leaf stage, were sprayed with an-aqueous conidia suspension of cucumber mildew (Erysiphe cichoracearum and Sphaerotheca fuliginea). On the following day, these plants were sprayQd to run-off with an aqueous spray liquor which contained 80~ of active ingredient and 20% of emulsifier, the percentages being based on the dry substance, and were placed in a green-house at from 20 to 22C and from 70 to 30% humidity. 20 days after application of the active ingredient, the extent of fungal infestation was determined.
Active ingredient Infestation of the leaves after from Example application of 0.025% strength aqueou~ active ingredient formulation Rating~ ~ % infestation 4.1 1 5 Comparative active ingredient 4 70 Untreated 5 100

Claims

1. An azolylmethylcycloalkanol of the formula I

(I) where R1 and R5 are identical or different and are each hydrogen or C1- to C4-alkyl;
R1 and R5 together with the carbon atom on which they are substituents are >C=CH-R7 or >CH-Z-R7, where Z is CH2, O, S, SO, SO2 or N-R5;
R7 is C1- to C8-alkyl, phenyl, biphenyl, naphthyl, hetero-aryl, benzyl or C3- to C8-cycloalkyl, where each of these radicals may be monosubstituted to trisubstituted by halogen, nitro, phenoxy, amino, C1- to C4-alkyl, C1- to C4-alkoxy or C1- to C4-haloalkyl, or is tetrahydropyranyl, or, where R1 and R5 together with the carbon atom on which they are substituents are >CH-Z-R7, R7 may additionally be hydrogen;
R2 and R3 are each hydrogen or C1- to C4-alkyl, or, where R1 and R5 together with the carbon atom on which they are substituents are >C=CH-R7, R2 and R3 together with the carbon atom on which they are substituents may addi-tionally be >C=CH-R7;
R4 and R8 are each hydrogen or C1- to C4 alkyl, or R3 and R4 together with the carbon atoms on which they are substituents are a saturated or unsaturated 5-membered or 6-membered carbocyclic ring, or R2, R3, R4 and R9 together with the carbon atoms on which they are substituents are an unsubstituted or halogen-substituted phenyl ring, or where R1 and R5 together with the carbon atom on which O.Z. 0050/41291 they are substituents are >C=CH-R7, R2 and R3 together with the carbon atom on which they are substituents may additionally be >C=CH-R7;
R6, R9 to R12 are each hydrogen, C1 to C8-alkyl, phenyl, biphenyl, naphthyl, heteroaryl, benzyl, dioxolanyl or C3-to C8-cycloalkyl, where each of these radicals may be monosubstituted to trisubstituted by halogen, nitro, phenoxy, amino, C1- to C4-alkyl, C1- to C4-alkoxy or C1- to C4-haloalkyl;
T is (CH2)n, =CR11R12, O or S;
n is an integer from 1 to 5, with the proviso that R1 to R12 are not simultaneously hydrogen, and with the proviso that R1 and R5 together are not or when R2 to R4 and R6 to R12 are hydrogen, and X is CH or N, and its plant-tolerated acid addition salts and metal complexes.

2. An azolylmethylcycloalkanol of the formula I as claimed in claim 1, wherein R7 is phenyl which is unsub-stituted or monosubstituted to trisubstituted by fluorine or chlorine.

3. A fungicide containing a carrier and a fungicidal amount of an azolylmethylcycloalkanol of the formula I

(I) where R1 and R5 are identical or different and are each hydrogen or C1- to C4-alkyl;
R1 and R5 together with the carbon atom on which they are O.Z. 0050/41291 substituents are >C=CH-R7 or >CH-Z-R7, where Z is CH2, O, S, SO, SO2 or N-R8;
R7 is C1- to C8-alkyl, phenyl, biphenyl, naphthyl, hetero-aryl, benzyl or C3- to C8-cycloalkyl, where each of these radicals may be monosubstituted to trisubstituted by halogen, nitro, phenoxy, amino, C1- to C4-alkyl, C1- to C4-alkoxy or C1- to C4-haloalkyl, or is tetrahydropyranyl, or, where Rl and R5 together with the carbon atom on which they are substituents are >CH-Z-R7, R7 may additionally be hydrogen;
R2 and R3 are each hydrogen or C1- to C4-alkyl, or, where R1 and R5 together with the carbon atom on which they are substituents are >C=CH-R7, R2 and R3 together with the carbon atom on which they are substituents may additionally be >C=CH-R7;
R4 and R8 are each hydrogen or C1- to C4 alkyl, or R3 and R4 together with the carbon atoms on which they are substituents are a saturated or unsaturated 5-membered or 6-membered carbocyclic ring, or R2, R3, R4 and R9 together with the carbon atoms on which they are substituents are an unsubstituted or halogen-substituted phenyl ring, or where R1 and R5 together with the carbon atom on which they are substituents are >C=CH-R7, R2 and R3 together with the carbon atom on which they are substituents may additionally be >C=CH-R7;
R6, R9 to R12 are each hydrogen, C1 to C8-alkyl, phenyl, biphenyl, naphthyl, heteroaryl, benzyl, dioxolanyl or C3-to C8-cycloalkyl, where each of these radicals may be monosubstituted to trisubstituted by halogen, nitro, phenoxy, amino, C1- to C4 alkyl, C1- to C4-alkoxy or C1- to C4-haloalkyl;
T is (CH2)n, =CR11R12, O or S;
n is an integer from 1 to 5, with the proviso that R1 to R12 are not simultaneously hydrogen, and with the proviso that R1 and R5 together are not O.Z. 0050/4129 or when R2 to R4 and R6 to R12 are hydrogen, and X is CH or N, and its plant-tolerated acid addition salts and metal complexes, or the plant-tolerated acid addition salt or metal complex thereof.

4. Method for controlling fungi, wherein a fun-gicidal amount of an azolylmethylcycloalkanol of the formula I

(I) where R1 and R5 are identical or different and are each hydrogen or C1- to C4-alkyl;
R1 and R5 together with the carbon atom on which they are substituents are >C=CH-R7 or >CH-Z-R7, where Z is CH2, O, S, SO, SO2 or N-R8;
R7 is C1- to C8-alkyl, phenyl, biphenyl, naphthyl, hetero-aryl, benzyl or C3- to C8-cycloalkyl, where each of these radicals may be monosubstituted to trisubstituted by halogen, nitro, phenoxy, amino, C1- to C4-alkyl, C1- to C4-alkoxy or C1- to C4-haloalkyl, or is tetrahydropyranyl, or, where R1 and R5 together with the carbon atom on which they are substituents are >CH-Z-R7, R7 may additionally be hydrogen;
R2 and R3 are each hydrogen or C1- to C4 alkyl, or, where R1 and R5 together with the carbon atom on which they are substituents are >C=CH-R7, R2 and R3 together with the carbon atom on which they are substituents may additionally be >C=CH-R7;

O.Z. 0050/41291 R4 and R8 are each hydrogen or C1- to C4 alkyl, or R3 and R4 together with the carbon atoms on which they are substituents are a saturated or unsaturated 5-membered or 6-membered carbocyclic ring, or R2, R3, R4 and R9 together with the carbon atoms on which they are substituents are an unsubstituted or halogen-substituted phenyl ring, or where R1 and R5 together with the carbon atom on which they are substituents are >C=CH-R7, R2 and R3 together with the carbon atom on which they are substituents may additionally be >C=CH-R7;
R6, R9 to R12 are each hydrogen, C, to C8-alkyl, phenyl, biphenyl, naphthyl, heteroaryl, benzyl, dioxolanyl or C3-to C9-cycloalkyl, where each of these radicals may be monosubstituted to trisubstituted by halogen, nitro, phenoxy, amino, C1- to C4-alkyl, C1- to C4-alkoxy or C1- to C4-haloalkyl;
T is (CH2)n; =CR11R12, O or S;
n is an integer from 1 to 5, with the proviso that R1 to R12 are not simultaneously hydrogen, and with the proviso that R1 and R5 together are not or when R2 to R4 and R6 to R12 are hydrogen, and X is CH or N, and its plant-tolerated acid addition salts and metal complexes, or the plant-tolerated acid addition salt or metal complex thereof, are or is allowed to act on fungi or on materials, surfaces, plants or seeds threatened by fungal attack.

5. A plant growth regulator containing a carrier and an azolylmethylcycloalkanol of the formula I

O.Z. 0050/41291 (I) where R1 and R5 are identical or different and are each hydrogen or C1- to C4-alkyl;
R1 and R5 together with the carbon atom on which they are substituents are >C=CH-R7 or >CH-Z-R7, where Z is CH2, O, S, SO, SO2 or N-R8;
R7 is C1- to C8-alkyl, phenyl, biphenyl, naphthyl, hetero-aryl, benzyl or C3- to C8-cycloalkyl, where each of these radicals may be monosubstituted to trisubstituted by halogen, nitro, phenoxy, amino, C1- to C4-alkyl, C1- to C4-alkoxy or C1- to C4-haloalkyl, or is tetrahydropyranyl, or, where R1 and R5 together with the carbon atom on which they are substituents are >CH-Z-R7, R7 may additionally be hydrogen;
R2 and R3 are each hydrogen or C1- to C4-alkyl, or, where R1 and R5 together with the carbon atom on which they are substituents are >C=CH-R7, R2 and R3 together with the carbon atom on which they are substituents may additionally be >C=CH-R7;
R4 and R8 are each hydrogen or C1- to C4 alkyl, or R3 and R4 together with the carbon atoms on which they are substituents are a saturated or unsaturated 5-membered or

6-membered carbocyclic ring, or R2, R3, R4 and R9 together with the carbon atoms on which they are substituents are an unsubstituted or halogen substituted phenyl ring, or where R1 and R5 together with the carbon atom on which they are substituents are >C=CH-R7, R2 and R3 together with tha carbon atom on which they are substituents may additionally be >C=CH-R7;

O.Z. 0050/41291 R6, R9 to R12 are each hydrogen, C1 to C8-alkyl, phenyl, biphenyl, naphthyl, heteroaryl, benzyl, dioxolanyl or C3-to C8-cycloalkyl, where each of these radicals may be monosubstituted to trisubstituted by halogen, nitro, phenoxy, amino, C1- to C4-alkyl, C1- to C4-alkoxy or C1- to C4-haloalkyl;
T is (CH2)n, =CR11R12, O or S;
n is an integer from 1 to 5, with the proviso that R1 to R12 are not simultaneously hydrogen, and with the proviso that R1 and R5 together are not or when R2 to R4 and R6 to R12 are hydrogen, and X is CH or N, and its plant-tolerated acid addition salts and metal complexes, or the plant-tolerated acid addition salt or metal complex thereof, as claimed in claim 1.
6. Method for regulating plant growth, wherein an amount, which has a regulatory effect, of an azolyl-methylcycloalkanol of the formula I

(I) where R1 and R5 are identical or different and are each hydrogen or C1- to C4-alkyl;
R1 and R5 together with the carbon atom on which they are substituents are >C=CH-R7 or >CH-Z-R7, where Z is CH2, O, S, SO, SO2 or N-R8;
R7 is C1- to C8-alkyl, phenyl, biphenyl, naphthyl, hetero-aryl, benzyl or C3- to C8-cycloalkyl, where each of these radicals may be monosubstituted to trisubstituted by O.Z. 0050/41291 halogen, nitro, phenoxy, amino, C1- to C4-alkyl, C1- to C4-alkoxy or C1- to C4-haloalkyl, or is tetrahydropyranyl, or, where R1 and R5 together with the carbon atom on which they are substituents are >CH-Z-R7, R7 may additionally be hydrogen;
R2 and R3 are each hydrogen or C1- to C4-alkyl, or, where R1 and R5 together with the carbon atom on which they are substituents are >C=CH-R7, R2 and R3 together with the carbon atom on which they are substituents may additionally be >C=CH-R7;
R4 and R8 are each hydrogen or C1- to C4 alkyl, or R3 and R4 together with the carbon atoms on which they are substituents are a saturated or unsaturated 5-membered or 6-membered carbocyclic ring, or R2, R3, R4 and R9 together with the carbon atoms on which they are substituents are an unsubstituted or halogen-substituted phenyl ring, or where R1 and R5 together with the carbon atom on which they are substituents are >C=CH-R7, R2 and R3 together with the carbon atom on which they are substituents may additionally be >C=CH-R7;
R5, R9 to R12 are each hydrogen, C1 to C8-alkyl, phenyl, biphenyl, naphthyl, heteroaryl, benzyl, dioxolanyl or C3-to Ca-cycloalkyl, where each of these radicals may be monosubstituted to trisubstituted by halogen, nitro, phenoxy, amino, C1- to C4-alkyl, C1- to C4-alkoxy or C1- to C4-haloalkyl;
T is (CH2)n, =CR11R12, O or S;
n is an integer from 1 to 5, with the proviso that R1 to R12 are not simultaneously hydrogen, and with the proviso that R1 and R5 together are not or when R2 to R4 and R5 to R12 are hydrogen, and O.Z. 0050/41291 X is CH or N, and its plant-tolerated acid addition salts and metal complexes, or the plant-tolerated acid addition salt or metal complex thereof, are or is allowed to act on crops or their habitat.

7. A compound of the formula I as claimed in claim 1 herein R2 R3 R4, R3 and R10 are each hydrogen, T is CH2, R1 and R5 are each =C=CH-, R7 is 4-chlorophenyl, R9 is phenyl and X is N.

8. A compound of the formula I as claimed in claim 1, wherein R2, R3, R4, R6 and R10 are each hydrogen, T is CH2, R1 and R5 are each =C=CH-, R7 is 4-chlorophenyl, R9 is methyl and X is N.