JPS5998061A - Novel azole compound - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION This invention provides novel α-aryl-α-R1-II-1-
1,2,4-) lyazole-1-ethanol compound and α-aryl-α-R-11-1-imidazole-1
- ethanol compounds (wherein R1 represents cyclopropyl halokenide bonded directly or via an alkyl to the alpha atom) and the above ethers and esters of ethanol (hereinafter referred to as compounds of this invention), compounds of this invention This article relates to the manufacturing method and its uses.

As used herein, the term alpha-carbon is intended to refer to the carbon atom of the ethanol moiety to which the R1 group, aryl group, and hydroxy group are attached.

The α-aryl group in the compounds of this invention may be an unsubstituted or substituted aromatic hydrocarbon (preferably phenyl) or an unsubstituted or substituted heteroaromatic ring bonded at one of the ring carbon atoms (e.g. , 0, N and S, preferably furyl, chenyl or pyridyl), are suitable.

Examples of particularly suitable α-aryl groups are unsubstituted or NO2, halogen, or unsubstituted or halogenated C alkyl, C2-5-5 alkenyl, C alkynyl, C al-51-5 koxy or C1-5 alkylthio, or phenyl mono- or di-substituted with a substituent selected from unsubstituted or substituted phenyl or phenoxy. Another example of particularly suitable α-aryl groups is M such as 3-pyridyl and 2-chenyl and 2-furyl, which are unsubstituted or monosubstituted with halogen or C1-5 alkyl. Examples of aromatic groups C are 5-Cβ-2-chenyl and 5-tert-butyl-2-furyl).

α-aryl groups are phenyl substituted with R2 and R3, where k and 1 (3 are independently H, halogen, or unsubstituted or halogenated C1-5 alkyl, C2-5 alkenyl, C2-5 alkynyl, c
l-5 alkoxy or C□-5 alkylthio, or unsubstituted or substituted phenyl or phenoxy, or N02).

When R2 and/or R contain halogen, examples thereof are F, C/(or Br. Examples of preferred phenyl substituents are CH3, Cl, Br%I, CH30°C6I-I5, CF3 and C2H5, Special Cl-l3
, C6I]5, especially Cβ. Generally, the phenyl substituent is preferably at the 2,4-position (eg, 2,4-diC1), and more preferably at the 4-position (mono-substituted).

When the hydroxy group of the compound of this invention is etherified, examples of the ether include methyl, allyl, propargyl, benzyl ether, etc. 17) CI -
5 alkyl”3-5 alkenyl, 1 (
:3-5 Alkynyl or aralkyl ether. Examples of the ester in which the hydroxy group is esterified include aliphatic carbon acid esters such as acetate.

The compounds of this invention have one or more chiral (ch
iral) center. Such compounds are usually obtained in the form of racemic or diastereomeric mixtures. However, these and other mixtures
If desired, complete or partial resolution into the individual compounds or desired isomeric mixtures can be carried out according to methods known per se.

A preferred population of compounds of this invention has the formula (Il, where
R□, R2 and R3 have the above meanings, Y is CH or N
It is a compound represented by the following.

Here, R1 is in particular a group G5 [wherein X□ is I-I, F%Cβ or Br (especially Cβ or 13r, especially C6), X2 is F, C1 or Br (especially Cl or Br, special!ncA), R4, R
5゜k is independently H,,C alkyl (e.g. CH3)
6 1-5 years old or halogen, A is 8 to CR7 or CR7R5-CI-IR (where CHR9 is attached to the halogenated cyclopropyl moiety), R7, Rs, R9 are independently I-1 or C Alkyl (eg, CI; I3), where R7 and R8 may be combined to form C3-6 cycloalkyl (n means 0 or 1).

Preferably, X and X2 are the same.

It is suitable that at least a part of k and Σ are C□-, alkyl, or CR7R8 is cycloalkyl.

When CI(7R8 is cycloalkyl, this group preferably contains 3 to 5 ring carbon atoms.

one or more of RR and R6 is I-5 In the case of halogen, F, C4 or Br are preferred.

Particularly preferred is C6 or Br. R4, R5, R6, R
When either R or R9 is C1-5alkyl, it is preferably CHa.

n is preferably 1.

The compounds of this invention have the formula ([[) (M is H1 metal or trialkylsilyl group, Y
(meaning of the main character ##)
It is obtained by reacting with oxirane (here, R1 has the above-mentioned meaning) or a reactive derivative of the above-mentioned oxirane, and optionally etherifying or esterifying the obtained ethanol compound.

This method also forms part of this invention.

When M is H in formula (II), the reaction is preferably carried out in the presence of a base.

The compounds of the invention can be used in free base form, in salt form (e.g. acid addition salt form, such as the fish salt form, or in alcoholate form, e.g. Na-ethalate) and in the form of a metal such as, for example, Cu or Zn. It can be obtained in the form of metal complexes with anions such as chloride, sulfate, and nitrate.

Acid addition salts, alcoholates and metal complexes can also be obtained by conventional methods from the corresponding free forms, and vice versa.

The compound of formula (I) is a compound of formula (III) (wherein □, R2 and R3 are as defined above) or a reactive functional derivative thereof (hereinafter referred to as reactive derivative),
It is obtained by reacting with the compound of formula (■) (listed above) and optionally etherifying or esterifying the obtained ethanol compound.

The method of the present invention can be used, for example, in 2-aryl-2-R□-
Oxirane (supra) For example, a compound of formula (III) is reacted with an azole of formula (n) as such (M=H) or with a metal salt thereof (M=gold metal, preferably an alkali metal salt, e.g. Na salt) under the reaction conditions. The reaction is carried out in an active solvent, for example dimethylformamide, at a temperature from room temperature to the boiling point of the reaction mixture, or a compound of formula (II) in which M is trialkylsilyl, for example trimethylsilyl, is combined with a solvent inert under the reaction conditions, for example In dimethylformamide in the presence of a catalytic amount of a base such as NaH.

The reaction is preferably carried out by heating, preferably at a temperature of 70-90°C.

Here, the term "reactive derivative" used for the above-mentioned 2-aryl-2-1-oxirane, such as the compound of formula (II), refers to the reaction with an azole.

It is intended to include any oxirane derivatives that result in the ethanol compounds of this invention. Various examples of such reactive derivatives are known to those skilled in the art, suitable examples of which are the corresponding halohydrins (where halogen is, for example, C4 or Br). The conditions for reacting the -aryl-2-R□-oxirane with the reactive derivative are known per se. A compound of formula (II) and a compound of formula (
The reaction of the compound of III) with the halohydrin derivative can be carried out under the conditions described for the reaction of oxirane compounds, but is preferably carried out in the presence of a further equivalent of base.

The ester and ether derivatives of the ethanol compounds of the invention are obtained by known esterification and etherification starting from the corresponding ethanol.

The compounds of the invention can be isolated and purified from the reaction mixture by methods known per se.

The above 2-aryl-2-kl-oxirane compounds are new. A suitable manufacturing method thereof is, for example, the formula (III) shown below.
This reaction is similar to the reaction used in the production of compounds. formula(
The compound of 1) is obtained by a) treating the corresponding halohydrin with a base, and b) forming a compound of the formula (V) (formula where n is 0 or 1, X is ) 10 or methyl sulfate, R13 is alkyl),
In the presence of a base (alkali metal hydride or hydroxide),
It can be obtained by reacting using a method similar to each known method. R13 is 68-18 alkyl, especially straight chain C
In the case of s-18 alkyl such as n-dodecyl, formula (V)
The compound also acts as a phase transfer catalyst.

Compounds of formula (IV) can also be obtained by known methods. A compound of the formula (lVa) (wherein, ■(2, R3, R4, R5, R6, N, X2, and n have the above-mentioned meanings, (Kalpa, R2, R3, R4, Rs, R6, A and n
is the meaning as defined above) or the formula (■) (wherein R2, R3, R4, R5, R6, A and n are the meanings defined above) klo is the protection of H or OH group. starting from a compound exhibiting a group, for example a tetrahydropyranyl group, add to its double bond a :C parent □X2 group (where X□ and ) can be obtained by removing the protecting group and then oxidizing it to a keto group. Addition and oxidation of the diCllX2 group can be carried out analogously to known methods.

Carbenes of the formula: It is obtained by pyrolysis (decarboxylation) at 80-120° C. (for example in glyme or diglyme-containing solvent mixtures) or c) by pyrolysis of c6H5HgcX3 (X is halogen), for example in benzene under reflux.

In formula (Vl), n is 1 and A is CR7R8-CI-I
The starting compound for R9 is obtained by alkylation of acetophenone with, for example, allyl halide, and in formula (■) where (A)n is a covalent bond or CR7Rs and R10 is hydrogen, it is optionally substituted with, for example, vinyl or an allyl-Grinard compound. obtained by the reaction of benzaldehyde.

If the method for producing the starting materials is not described, they are known or can be obtained by methods described below or similar to known methods.

The compounds of this invention have been shown to exhibit interesting biological properties, particularly antifungal activity, and to be suitable for use as medicaments for the treatment of fungal diseases in animals and other animals. Antifungal activity is determined by in vitro tests, such as in vitro serial dilution tests carried out against various families and types of fungi such as yeasts, filamentous fungi and dermoid fungi at concentrations of about 0.05 to about 50 μI/ml. approximately 10 to 10 (1 &/K body weight) for mice infected intravaginally with Candida albicans
This is confirmed by an in vivo test with systemic and oral application at a dose of 1.5 g.

In the above applications, the dosage will, of course, vary depending on the compound used, the method of administration and the treatment desired.

However, in general, 1 to 100 kg/kg of animal weight is
Satisfactory results are obtained when the daily use is preferably administered in divided doses 2 to 4 times a day or in the form of a sustained release formulation. For large animals, the corresponding daily dose is 70 to 20
For example, a dosage form suitable for oral administration is one consisting of 17.5 to 1000 R9.

The compounds of this invention can be prepared and used both in free base form and in the form of pharmaceutically (or veterinarily) acceptable salts (acid addition salts or alcoholates), metal complexes, ethers or esters. Generally, the salt exhibits the same order of activity as the free base.

Acids that can be used for the production of acid addition salts include, for example, hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, fumaric acid, naphthalene-1,5-
Contains disulfonic acid.

The compounds of this invention are commonly used in pharmaceutical (or veterinary) medicine.
It can be mixed with an acceptable inert carrier and, if desired, other excipients. They can be administered in unit dosage forms for internal use such as tablets or capsules, and can be administered topically or parenterally in conventional forms such as ointments or creams.

The concentration of active ingredient will, of course, vary depending on the compound used, the desired treatment and mode of administration. However, in general, satisfactory results are obtained at concentrations of from 0.05 to 5, especially from 0 to 1% by weight, for example in topical administration forms.

Compounds of this invention are labeled as ketoconazole (1,
The lj compound can be used in the same manner as known methods. In particular, in formula (I), A is CR7R8
-CHR9 exhibits useful pharmaceutical activity.

The appropriate daily dosage for a particular compound of this invention will depend on a variety of factors, such as relative activity. This is, for example, 2-(4-chlorophenyl)-4-(2°2-dichlorocyclopropyl)-3,3-dimethyl! in the mouse vaginal candidiasis model. -1-c
4 x 12, 5 my
Recovery was achieved by oral administration of 1 kg/kg body weight. Therefore, the compounds of this invention can be used in the same dosage as ketoconazole and in the same dosage.

The free form or pesticide-acceptable salts of the compounds of this invention (
Acid addition salts or alcoholates), metal complexes, ether or ester forms are also useful as fungicides for combating phytopathogenic fungi.

Its high antifungal activity is due to Uromyces apendiculatus (blister rust) on climbing beans, other rusts (Hemileia, Puccinia, etc.) on coffee, wheat, geraniums, and goldfish, and Erysiphae sycolacearum on cucumbers. , and other powdery mildew fungi on wheat, barley, apples, and grapes (
Approximately 0.00 for E. graminis, f. sp. trisici, E. graminis f., sp.
Confirmed by in vitro tests carried out at test concentrations of 0.08 to 0.5%. Another interesting activity is about 0.8 to 200' PPm, especially against U. mayzis.
It was observed in in vitro studies conducted at test concentrations of about 10 to 160 ppm (corrected per volume of substrate) for Rhizoctonia nlanii.

Since these tests showed good tolerability to plants and good whole-plant action, the compounds of the invention are suitable for use against phytopathogenic fungi such as Basidiomycetes, Ascomycetes and Deuteromycetes, especially P. Peepi, Hemireia, Spp., Uromyces.
Basidiomycetes of the order Ureginales (rusts) such as Sp. sp., Ascomycetes of the order Erysiphalales (powdery mildew) such as Erysiphae sp., Podosphaera sp., and Uncinula sp., and Forma Used in the treatment of plants, seeds and soil to combat , Rhizoctonia and Helminthosporium.

The use of the compound of this invention includes the compound used, the object to be treated (
different types of fungi such as plants, soil, seeds), treatment method (f!l, dipping, liquid application, spraying, powder application, application), treatment purpose (preventive or therapeutic), type of fungus to be treated, and application time. Depends on factors.

Generally, for plant or soil treatment, the compounds of this invention are applied at about 0. '00' 5 to 2.0, preferably about 0.
Satisfactory results are obtained when used in amounts of 0.01 to IKg/hectur. If desired, the treatment can be repeated at intervals of, for example, 8 to 30 days. When the compounds of this invention are used for seed treatment, about 0.05 to 0.5
Satisfactory results are obtained using the compounds of the invention in amounts of, preferably about 0.1 to 0.3 g/Kg of seed.

As used herein, the term soil shall include any common medium, natural or man-made.

The compounds of this invention are suitable for use in soybeans, coffee, ornamental plants (particularly geraniums, roses), vegetables (e.g. peas, cucumbers, celery, tomatoes and bean plants), sugar radish, sugar cane, cotton, flax, corn. It can be used on a number of crops, such as corn), vineyards, pears and drupes (apples, prunus, prunus), and especially on cereals (e.g. wheat, prunus).
Suitable for use on wheat (e.g. oats, barley), especially wheat.

Particularly suitable for agricultural use, compounds of the invention are of the formula (I)
A subgroup of compounds of formula (I) which exhibit other useful fungicidal activities are those where Xl and X2 are bromine, and (
A) n is CH(C1-4 alkyl)-CI-IR9 and/or R4 is C1-4 alkyl (e.g. CH
3).

The invention also provides fungicidal compositions comprising a compound of the invention in free form or in its agriculturally acceptable salt, metal complex, ether or ester form as a fungicide and an agriculturally acceptable diluent. It is something. This composition is
They are obtained in conventional manner, for example by mixing the compounds of the invention with other ingredients such as diluents and optionally surfactants.

As used herein, the term diluent refers to a liquid or solid agriculturally acceptable material which is capable of providing an easy and convenient form of application to the active ingredient, i.e. diluting the active ingredient to a normal or desired strength of activity. means. Examples of such diluents are talc, kaolin, diatomaceous earth, xylene or water.

In particular, formulations used in spray form, such as thick liquids for aqueous dispersion or as wettable powders, may contain surfactant wetting and dispersing agents such as, for example, condensates of formaldehyde and naphthalene sulfonates, alkyl sulfonates of the alkylaryl sulfonate family, ethoxylated alkyl phenols, and wetting and dispersing agents. can contain agents.

Generally, the formulations contain from 0.01 to 90% by weight of active ingredient, from 20% to 20% fungicidally acceptable surfactants, and from 10 to 99.99% diluent. Compositions in the A-thickness form, such as A-thickness emulsions, generally contain about 2 to 90%;
Preferably, it contains 5 to 70% by weight of active ingredient. Preparations in application form generally contain from 0.0005 to 10% by weight of a compound of the invention as active ingredient.

In addition to the usual diluents and surfactants, the compositions of this invention may also contain special purpose additives, such as stabilizers, inerts. (In the case of solid formulations using carriers with active surfaces), adhesion improvers to plants, corrosion inhibitors, antifoaming agents and dyes can be included. In addition, other fungicides with similar or complementary activity or other useful substances such as insecticides can be present in the formulation.

An example of a method for producing a plant fungicide is as follows.

a. Powder preparation for hydration 25 parts of the compound of this invention are mixed and ground with 25 parts of synthetic fine silica, 2 parts of sodium lauryl sulfate, 2 parts of lithium, 3 parts of sodium ligninsulfonate and 45 parts of starchy kaolin, with an average particle size of about 5 microns. Make into powder. The resulting irrigation agent is used as a spray solution (diluted with water, which is applied by foliar spraying and root soaking).

b. Condyle 1. 0.5 parts of a binder (nonionic surfactant) was sprayed onto 94.5 parts of quartz sand placed in a 4L tumbler mixer, and the whole was thoroughly mixed. Next, 5 parts by weight of the compound of the present invention are added and mixed well to obtain a granular preparation with a particle size range of 0.3 to Q.7 mm. The granules can be applied by adding them to the soil near the treated plants.

C. 25 parts by weight of the compound of this invention are mixed with 10 parts by weight of emulsifier and 65 parts by weight of xylene. This concentrate is diluted with water to the desired concentration.

d. Seed Dressing 45 parts of the compound of this invention are mixed with 1.5 parts of cyamylphenoldecacrylic ether additive, 2 parts of spindle oil, 51 parts of finely ground talcum and 0.5 part of Rhodamine B dye. The mixture was milled at 10,000 rpm using a Contrabrex mill.
pulverize to an average particle size of 20 microns or less.

The resulting dry powder has good cohesion and can be applied to the seeds, for example by mixing for 2 to 5 minutes in a slowly rotating container.

[Final compound]

Example 1 2-(4-chlorophenyl)-4-(2.2
-dichlorocyclopropyl)-3,3-dimethyl-1-
< i H- 1.2.4- ) Riazol-1-yl) Production of butacy-2-ol.

a) 5.1 g of dodecyl-dimethylsulfonium methyl sulfate was converted into 1-(4-chlorophenyl)-3-
(2m2-cyclocyclopropyl)-2,2-dimethylpropan-1-one (3.0 fl dry)-toluene is added to a solution of 30 nxl at room temperature and the mixture is mixed for 15 minutes. Add 1.1 g of powdered KOH to the resulting suspension.
was added and the mixture was stirred at 35°C for 2 hours. After cooling, the reaction mixture is poured onto ice and extracted with diethyl ether. The organic extract was washed three times with water, then saturated Na
Wash with aqueous Cl, dry over MgS04, and concentrate under reduced pressure. The residue is 2-(4-chlorophenyl) ~
2-[2-(2,2-')chlorocyclopropyl) -
It is a colorless oil consisting of 50% 1,1-dimethylethyl]oxirane and 50fO dodecylmethyl sulfide.

b) The crude oxirane reaction product was heated to 90°C 1,2
．． 4-) Add dropwise to 1.0 g of Riazole within 10 minutes and stir the mixture for 18 hours while increasing the reaction temperature to 90''.

After cooling, the reaction mixture is poured onto ice and extracted with CH2C. The organic extract was washed successively with water and saturated NaC (
1 aqueous solution, dried over M g SO 4 and the solvent was removed under reduced pressure. Chromatography on silica gel first with a hexane fraction/ethyl acetate (first 9:11 then 1:1), then with ethyl acetate as eluent, and then crystallization from a diethyl ether/hexane fraction yielding colorless crystals with mpH 7-123°. The title compound is obtained as a diastereomeric mixture.

Example 2 In the same manner as in Example 1, a compound of the following formula (Ia) is obtained by reacting an azole with the corresponding oxirane.

= center center center 1 center 1 1 center 1 center E S + b center 1
绝绝
The center of the center, σ88, the shape of the d-engine
Winter - 11 - Hehehehehehe ~ Go to N. * Diastereomeric mixture. EAc - ethyl acetate.

**Isomer mixture.

[Intermediate]

Example 3 l-(4-chlorophenyl)-3-(2,2-dichlorocyclopropyl)-212-dimethylpropane-1
- Manufacture of on.

a) Powder] ('01-1289 and toluene 100.w
4-chlorophenyl isopropyl ketone 4
5.6 g were added to the solution under stirring at room temperature for 30 minutes, followed by the addition of 8.1 g of tetrabutylammonium bromide, thereby raising the internal temperature to 30'C. After stirring for 2 hours, a solution of 28.7 f/allyl chloride and 100 ml of toluene is added dropwise at room temperature and the mixture is stirred overnight at room temperature. The mixture was poured onto ice water, extracted with ether, the organic layers were combined and washed successively with water and saturated aqueous NaC,
Dry with MI7S04 and concentrate.

The residual crude product was fractionated to give 1-(chlorophenyl)-2,2-dimethyl-4 as a colorless oil with a BP of 9510.4% Hg.
- obtain penten-1-one.

b) Add 500 g of 50% NaOH aqueous solution to a solution of 1-(4-chlorophenyl)-2+2-'; methyl-4-penten-1-one 641 and 3500 ml of CHCl at 0°C, and add triethylbenzylammonium chloride to this mixture. Add 5g of (TEBA) little by little over 15 minutes. After the addition is complete, the mixture is stirred for 8 hours at 0-5°C, then diluted with 500 ml of CtlCl a and stirred for a further 18 hours at room temperature. The reaction mixture is poured onto ice and extracted with CH2Ce2, the organic layers are combined, washed with water, dried over MgS04, and concentrated under reduced pressure. The pure title compound was subjected to silica gel chromatography using hexane fraction/diethyl ether (1-3%) as the eluent, and the Rf of silica gel thin layer chromatography was 0.23 (eluent: hexane fraction/diethyl ether - 96:4). get.

Example 4 Analogously to Example 3b, the following compound of formula (IVa) is obtained by reaction of a dihalocarbene with the corresponding unsaturated compound of formula (Vl).

Example 5 Preparation of 4-chlorophenyl-(2,2-cyclo-1-methylcyclopropyl)ketone.

To a solution of 7.0 g of 1-(4-chlorophenyl)-2-methyl-2-propen-1-one and 70 ml of chloroform, 16y of a 50% aqueous NaOH solution was gradually added at O'C with vigorous stirring, and then triethylbenzylammonium chloride was added. Add 4.3y. After the addition is complete, remove the cooling bath until a strongly exothermic reaction begins.

The reactants were cooled again and the reaction temperature reached 34-4 for the first 1 hour.
0, then gradually allow the temperature to drop to room temperature.

After 5 hours of reaction, the mixture is poured onto ice and extracted with diethyl ether. The organic extracts were combined, washed with water, and M g S
04 and concentrated under reduced pressure. The residue was chromatographed on silica gel using hexane fraction/diethyl ether-9=1, 0 nD=1.5689, Rf of thin layer chromatography=
0.24 (hexane fraction/diethylny 7/I
/-9:1 use) to obtain the title compound.

Patent applicant: Sand Akchengesellschaft, patent attorney Aoyama Aoyama, and 1 other person

Claims (1)

[Scope of Claims] (1) Novel α-aryl-α-R1-I H-1,
2゜4-triazole-1-ethanol compound and α
- Free forms of aryl-α-R1-iH-imidazole-bone 1-ethanol compounds (wherein R1 represents a cyclopropyl halide bonded directly or via an alkyl to the α-carbon atom), and acid addition salts thereof. , alcoholates, metal complexes, ether and ester forms. (2) Formula (IlC In the formula, k has the meaning described in the above item 1, R2 and R3
is independently hydrogen, or halogen, or unsubstituted or halogenated C0-5 alkyl, 2-5 alkenyl, C alkynyl, C2-5 C1-5 alkoxy or C alkylthio, or unsubstituted or Substituted phenyl or phenoxy, or N02, ■64CH or N) or its acid addition salt. Alcoholates, metal complexes, ethers or esters. A compound according to claim 1. (3) R□ is a group (G) 5 [wherein, X□ is H%F, C/(or Br (especially Cβ
or Br, especially Cl), X2 is F, Cg-i or B
r (especially Cl or Br, especially Cl), R4, Rs,
R6 is independently H, Cl-5 alkyl (e.g., CH)
or halogen, A is Ck7R8 or CR7R8-C
HR9 (where c I-I R9 is bonded to a halogen, cyclopropyl moiety), R7, R8゜R9 are independently tho or C1-5 alkyl (e.g., CH), where R and 3. The compound according to claim 2, wherein R8 may be bonded to form C3-6 cycloalkyl, and n means O or 1. +4]2-(4-chlorophenyl) -4-(2,2-
dichlorocyclopropyl)-3,3-dimethyl-1'-
The compound according to claim 3, which is (-i I-1-1,2,4-)riazol-1-yl)butan-2-ol. (5) R2, R3, (A)n, R4, Rs, R6,
Xl. X2 and Y are each a) 4-(:l, H, C(CH3)2-CH2,
H, I-(, i(, Br, Br, Nd) 4-ci
, H, C (C:H3)2. H, H, H, CI, CI
, N. The compound according to claim 3, which is N. M(3) (M is H1 metal or trialkylsilyl group, Y
is the meaning described in Section 2 above) □- to the corresponding 2-aryl-2-
The resulting ethanol compound is optionally etherified or esterified by reacting with an oxirane (where k□ has the meaning as defined in item 1 above) or a reactive functional derivative of the oxirane, and the resulting compound is converted into free form or 6. A process for the preparation of a compound according to any one of claims 1 to 5, comprising recovering it in the form of an acid addition salt, alcoholate or metal complex. (7) It is obtained by the method described in claim 6. A compound according to claim 1. (8) Free forms of the compounds according to claims 1 to 5'! 6 and 7 or agriculturally acceptable salts thereof;
Plant fungicidal side consisting of metal complexes, ether or ester forms and agriculturally acceptable diluents. (9) The free form of the compound according to claims 1 to 5 and 7 or its pharmaceutically acceptable salt, metal complex, ether or ester form is pharmaceutically or veterinarily acceptable. consisting of a diluent or carrier,
Pharmaceutical or veterinary medicine.