CS259870B2 - Fungicide and method of its efficient substance production - Google Patents

Abstract

Fungicidal plant protection agent it contains derivatives of α-aryl- -IH-azole-1-ethanol of formula I wherein R is hydrogen, halogen, C 1-5 alkyl, phenyl optionally substituted with halogen, C 1-3 alkoxy or nitro, R 1 is C 1-8 alkyl, C 1-6 alkenyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl C 1-3 alkylene, Az means 1,2,4-triazole-1 -yl or imidazol-1-yl and Z is hydrogen or C 1-5 alkyl. The compounds of formula (I) are prepared are run by reacting an oxirane of formula II or its halohydrin, with 1,2,4-triazole or imidazole. The fungicidal agent is for use protection of plants against pathogenic fungi.

Description

The present invention relates to a fungicidal composition for the protection of plants against pathogenic fungi and to a process for the preparation thereof. It contains as active ingredient the .alpha.-aryl-1H-azole-1-ethanol derivatives of the general formula I.

According to the invention, alpha-substituted alpha-ethynyl-substituted phenyl) -1H-azol-1-ethanols are prepared in the alpha position, wherein the azole group is 1,2,4-triazol-1-yl or imidazol-1-yl, the ethynyl group is unsubstituted or and ethers of such ethanol compounds.

The fungicidal composition according to the invention contains as active ingredient the α-aryl-1H-azole-1-ethanol derivatives of the general formula I

OZ

AND

R 1 (O where R is hydrogen, halogen, C 1 -C 5 alkyl, phenyl optionally substituted by halogen, C 1 -C 5 alkoxy or nitro,

R 1 is C 3 -C 8 alkyl, C 2 -C 8 alkenyl, C 3 -C 6 cycloalkyl or C 3 -C 6 cycloalkylalkylene in C 1 -C 3 cycloalkyl and in C 1 -C 3 alkylene,

Az 1,2,4-triazol-1-yl or imidazol-1-yl a

Z is hydrogen or alkyl of up to 5 carbon atoms, in free form or in the form of acid addition salts.

The compounds prepared according to the invention contain one or more chiral centers; such compounds are generally obtained in the form of racemic or diastereomeric mixtures. However, such and similar mixtures may optionally be either completely or partially separated into the individual isomers or into the desired isomer mixtures by methods known per se.

When R is a halogen atom, it is, for example, a chlorine, bromine or iodine atom.

When R1 includes an alkylene moiety of 1 to 3 carbon atoms, this moiety is, for example, methylene CH2 or methylmethylene (CH2CH3).

When R1 is C1-C8alkyl, it is preferably isopropyl or tert-butyl.

When R1 is a halogen substituted alkyl of 1 to 8 carbon atoms, an alkenyl group of 2 to 8 carbon atoms or an alkynyl group of 2 to 8 carbon atoms, the halogen substituent may be a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

When R 1 represents or includes a C 3 -C 6 cycloalkyl moiety, such cycloalkyl moiety is preferably a cyclopropyl group or a cyclopropyl moiety. The ethynyl substituent is generally in the meta or para position of the phenyl group, preferably in the para position.

When the ethanol hydroxyl group of the compounds prepared by the process of the invention is etherified, such ethers are, for example, C 1 -C 5 alkyl ethers, such as methyl ethers.

The compounds of the invention are prepared by reacting 2- (ethynyl substituted phenyl) 2-hydrocarbyloxirane, wherein the ethynyl group may be substituted or a reactive derivative thereof with 1,2,4-trlazole or amidazole followed by optionally substituting an ethyl moiety, if unsubstituted, with an atom halogenation and / or etherification of the ethanol compound thus obtained.

Thus, the active compounds of the formula I are prepared by reacting an oxirane of the formula II

R-C

wherein R and R 1 are as defined above, or a halohydrin derivative thereof, with a heterocyclic compound selected from the group consisting of 1,2,4-triazole or imidazole. Optionally, in a compound of formula I wherein R 1 and A 2 are as defined above and R and Z are hydrogen, the hydrogen atom of the ethynyl group is replaced by a halogen atom. The obtained ethanol compound of formula (I), wherein R, R 1 and Az are as defined above and Z is hydrogen, is optionally etherified by reaction with a C 1 -C 5 alkyl halide. This gives the compound of formula I in free form or in the form of an acid addition salt.

The whole procedure is clearly described in the following text.

Thus, the compounds of formula (1) are prepared by reacting an oxirane of formula (II)

239870

R-

(Η) wherein R, R 1 and X are as defined above, or a functional derivative thereof, with 1,2,4-triazole or imidazole and optionally etherify the ethanol compound thus obtained, or

b) for the preparation of a compound of the general formula Ib

C ~ C

OlH, // i

X fy (1b) wherein R 1, X and Az are as defined above and wherein Y is a halogen atom, is replaced by the hydrogen of the ethynyl group in the compound of formula (1c):

OH fy /

R <1 (ic) wherein R 1, X and Az are as defined above, with a Y group (halogen) and optionally etherification of the ethanol compound thus obtained.

The process of paragraph a) is a reaction known per se for the preparation of azole-1-ethanes by reaction of oxirane with azole. The reaction may be carried out under conditions similar to those known per se: it is preferable to use the azole in the form of a salt (e.g. alkali metal salt such as sodium or potassium salt), in trialkylsilyl form (e.g. trimethylsilyl form) or to carry out the reaction in acid-binding.

The reaction with the oxirane according to a) is usually carried out in a solvent inert under the reaction conditions, such as dimethylformamide. A suitable reaction temperature is between room temperature and the reflux temperature of the reaction mixture; when the azole is in the trialkylsilyl form, the temperature is generally higher than room temperature, for example 70 to 90 ° C. when the trialkylsilylazole is reacted, the reaction is generally carried out in the presence of a base, for example sodium hydride.

The term "reactive functional derivative" used in the context of 2-aryl-2-R 1 -oxiranes as compounds of formula II includes any oxirane derivatives from which the ethanol compound of the invention is obtained by reaction with azole. Various examples of such reactive derivatives are known to those skilled in the art. Suitable examples include the corresponding halohydrins, the halogen atom being, for example, a chlorine atom or a bromine atom.

The conditions under which azoles can react with the reactive functional derivatives of the 2-aryl-2-R 1 -oxiranes defined above are known per se. The reaction of the azole with the halohydrin derivative of the compound of formula (II) may be carried out under conditions known for the reaction with oxirane compounds, but is generally carried out in the presence of an additional base equivalent.

The replacement of the ethynyl hydrogen atom in the compound of formula (Ic) by a halogen atom is also carried out in a manner known per se for this type of substitution reaction. It may be carried out either directly or by reaction of a compound of formula 1c with a halogen cationic donor such as an alkali metal hypochlorite, for example sodium hypochlorite or potassium hypochlorite, N-chlorosuccinimide or N-bromosuccinimide or carbon tetrachloride (in the case of strong carbon tetrachloride). alkaline medium) or via a di-Y-addition product followed by cleavage of the HY group from the addition product.

The ether derivatives of the ethanol compounds according to the invention can be obtained by esterifications known per se from the corresponding ethanol. Suitable O-alkylating agents are, for example, the corresponding halides, for example iodides, such as methyl iodide.

The compounds prepared by the process of the invention are isolated from the reaction mixture in which they are formed by known methods. They are obtained in free form or in the form of a salt or in the form of a metal complex, for example as addition salts with organic or inorganic acid, for example as hydrochlorides, or obtained in the form of an alcoholate, for example sodium ethanolate or complexed with a metal, for example with copper or zinc; anions selected from the group consisting of chloride, sulfate and nitrate.

Unless the process for producing any starting material is specifically described, these compounds are known or can be prepared and purified by methods known per se or by methods similar to those described or known per se.

The compounds of formula I, prepared by the process of the invention, in free form or in the form of agriculturally acceptable salts or complexes, are useful fungicides in combating phytopathogenic fungi. Their preferred fungicidal activity was determined in in vivo assays at a concentration of about 0.0008 to 0.05% against Uromyces appendiculatus. Legume rust, against other rust-causing fungi (such as Hemiknc, Puccinia) on coffee, wheat, geraniums, Erysiphe cichoracearum powdery mildew, and against other fungi referred to as powdery mildew (Erysiphe graminis wheat mildew, Erysiphe graminis) Apple powdery mildew Podosphaera leucotricha, powdery mildew of Uncinula necator] on wheat, barley, apple and grapevine Another interesting activity is observed in vitro against Ustilago maydis maize and in vivo against Rhízoctonia solani potato spice. The compounds of the formula (1) prepared according to the process of the invention are therefore used for the treatment of plants, seeds and soil to combat phytopathic fungi, for example basidiomas cet Basidiomycetes of the rust species Uredinales such as Puccinia spp, Hemileia spp, Uromyces spp, the fungus Ascomycetes of the powdery mildew species Erysiphales, such as Erysiphe spp. Apple powdery mildew Podosphaera spp. and powdery mildew Uncinula spp. as well as Phoma flax drying fungi, Rhizoctonia, Hehninthosporium, Pyricularia, Pellicularia (= Corticium), Thielaviapsis and Stersum spp.

The amount in which the compounds of formula I are used depends on various factors such as the type of compound used, the subject (plant, soil, seeds) treated, the type of treatment (dipping, sprinkling, spraying, dusting, pickling) prophylactic or therapeutic), type of fungus to be destroyed, application time. In general, satisfactory results are obtained when the compound of the formula I is used in an amount of 0.005 to 2.0, preferably about 0.01 to 1 kg / ha, in the case of plant or soil treatment: for example, 0.04 to 0.125 kg of active substances per hectare in the case of crops such as cereals, or at a concentration of 1 to 5 g of active substance per hectare in the case of fruit, grapes and vegetables (at application rates of 300 to 1 000 l / ha depending on leaf size or volume) The treatment may optionally be repeated, for example at intervals of 8 to 30 days.

When a compound of formula I is used for seed treatment, generally satisfactory results are obtained when the compound is used in an amount of about 0.05 to 0.5, preferably 0.1 to 0.3 g / kg seed.

The term soil means here any plant environment, whether natural or artificial.

The compounds of the formula I prepared according to the invention can be used for the treatment of a large number of crops such as soy, coffee, ornamental flowers (for example pelargonia and rose, vegetables (for example legumes, cucumbers, celery, tomatoes, berry plants), diabetes , sugarcane, cotton, flax, corn, grapevine, pome fruits and drupes (for example, apples, plums, pears) and cereals (for example, wheat, oats, barley, rice).

In view of the good tolerability of the numerous compounds of the formula I prepared by the process according to the invention, they are particularly suitable for fungicidal treatments where such good tolerance is desirable or necessary, for example in the case of fruits such as apples. Various compounds of formula I, such as those of Example 2.33, also have a favorable curative effect.

Particularly favorable results are obtained, for example, with compounds of the formula I having at least one of the following characteristics:

X is hydrogen, C-OR is in para,

R represents a hydrogen atom, a chlorine or bromine atom, a methyl group, a butyl group (for example an n-butyl or tert-butyl group) or a phenyl group unsubstituted or substituted, especially a bromine substituted or unsubstituted phenyl group, in particular unsubstituted phenyl group,

R 1 isopropyl, tert-butyl, cycloalkyl of 3 to 6 carbon atoms, in particular cyclopropyl, or cycloalkylalkylene of 3 to 6 carbon atoms in the cycloalkyl moiety of up to about 3 carbon atoms in the alkylene moiety, especially cyclopropylalkylene of 1 up to 3 carbon atoms in the alkylene moiety, in particular a cyclopropylroethylmethylene group (cyclopropyl-CH (CH3)),

Az 1,2,4-triazol-1-yl.

The invention also relates to fungicidal compositions comprising, as a fungicidally active compound, a compound of the formula I prepared according to the process of the invention, in free form or in the form of a fungicidally acceptable salt or complexed together with a fungicidally suitable diluent. They are obtained in a manner known per se by mixing the active compound of the formula I with a diluent and optionally with additional components, such as surfactants.

As used herein, the term &quot; diluent &quot; refers to liquid or solid fungicidally acceptable substances which may be added to

5 9?. In order to convert the active compound of formula (I) into an easier and more convenient form, or to dilute the active compound of formula (I) to a useful or desired level of efficacy. Examples of such diluents are talc, kaolin, diatomaceous earth, xylene or water.

In particular, the compositions are used in the form of sprays, such as water-dispersible concentrates or wettable. powders, which may contain surfactants such as wetting and dispersing agents, for example the condensation products of formaldehyde and naphthalene sulfonate, alkylarylsulfonate, lignin sulfonate, fatty alkyisulfate, ethoxylated alkylpheuol and ethoxylated fatty alcohol.

In general, the compositions contain from 0.01 to 90% by weight of active ingredient, from 0 to 20% of a fungicidal surfactant and from 10 to 99.99% of at least one diluent. Concentrated forms of fungicidal compositions, for example emulsion concentrates, generally contain 2 to 90%, preferably 5 to 70% by weight of active ingredient. The dosage forms of the fungicidal compositions according to the invention generally contain from 0.0005 to 10% by weight of active compound of the general formula 1. Typical sprayable suspensions contain from 0.0005 to 0.05, preferably 0.001 to 0.02%, for example 0.001, 0.002 or 0.005 why. active compounds of the formula I

In addition to conventional diluents and surfactants, the fungicidal compositions of the invention may contain other special additives with special tasks, such as stabilizers, deactivators (for solid or active surface carriers), plant adhesion promoters, corrosion inhibitors, anti-foaming agents. and dyes. In addition, such fungicidal compositions according to the invention may contain other fungicidal active compounds with similar or complementary fungicidal action, such as sulfur, bromothalonil, dithiocarbamates such as mancozeb, maneb, zineb, adjuncts, trichloromethanesulfenylphthalminides and analogs thereof such as captan, captaol and foipet, benzimidazoles such as benomyl or longer beneficial agents such as insecticides. The fungicidal compositions of the invention may take the following forms: wettable powders

10 parts of a compound of formula I are mixed with 4 parts of synthetic fine silica, 3 parts of sodium lauryl sulfate, 7 parts of sodium silicate and 68 parts of finely divided kaolin and 10 parts of diatomaceous earth and are ground to a mean particle diameter of approximately 5 microns. The resulting wettable powder is diluted with water before use as a spray liquid which can be applied to the leaf and to the roots.

bj Granule

94.5 parts by weight of quartz sand in a tumbler mixer are sprayed with 0.5 parts by weight of binder (nonionic surfactant J and mixed thoroughly), then 5 parts by weight of the compound of formula (I) are added and mixed thoroughly until a granular composition is obtained. A particle diameter of 0.3 to 0.7 mm The granules can be applied to the soil around the treated plant.

c) Emulsion Concentrate

25 parts of the active compound of the formula I are mixed with 10 parts by weight of emulsifier and 65 parts by weight of xylene. The concentrate is diluted with water to the desired concentration.

(d) Seed dressing

45 parts of a compound of the formula I are mixed with 1.5 parts of a diamylphenolecylglycol etherethylene oxide addition product, 2 parts by weight of spindle oil, 51 parts by weight of fine talc and 0.5 parts by weight of Rhododine B dye. The mixture is milled in a 10,000 rpm cotrapex mill. / m.in to an average particle diameter of less than 20 microns. The resulting dry powder has good adhesion and can be applied to the seeds, for example by mixing for 2 to 5 minutes in a slowly rotating vessel.

The invention is further illustrated by the following non-limiting examples. Temperatures are given in ° C. R _f values obtained by silica gel chromatography (thin layer chromatography e.

Example 1

2- (4-Ethinyl-phenyl) -3,3-dimethyl-1- (1H-1,2,4-triazol-1-yl) butan-2-ol

At room temperature, 17.2 g of dodecyldimethylsulfoniuraroethylsulfate is added to a solution of 6.5 g of 1- (4-ethylphenyl) -2,2-dimethyl-propan-1-one in 80 ml of absolute toluene. The mixture was stirred for 15 minutes, then 3.8 g of powdered potassium hydroxide was added, and the mixture was further stirred at 35 ° C for 22 hours. The reaction mixture is poured onto ice, the pPI is adjusted to 7 with 6 N sulfuric acid and extracted with diethyl ether. The organic phase was washed with water, dried (sodium sulfate) and evaporated in vacuo. The residue containing 2- (4-ethynylphenyl) -2- (1,1-dimethylethyl) oxirane is used for the next reaction without purification.

The residue was added dropwise over 10 minutes at 90 ^{° C;} C to a suspension of 4 g of 1,2,4-triazole and 14.5 g of potassium carbonate in 80 ml of absolute dimethylformamide and stirred for 4 hours at 90 ° C. The reaction mixture was then cooled, poured onto ice and extracted with diethyl ether. The ether solution was washed with water, dried and concentrated in vacuo. The residue was stirred with hexane, the insoluble solid product was filtered off and recrystallized from hexane / toluene. The product was obtained as colorless crystals of melting point 101 DEG C. _(Rf = 0.35 ethylacetate / hexane 6: 4).

Example 2

Similarly to Example 1, the following compounds of Table I of formula (I) wherein X is hydrogen and R = C = C- is in the para-position unless otherwise stated are prepared starting from the corresponding ketones of formula (I). of formula IV and compounds of formula I are prepared via oxiranes of formula II.

The notes in the table have the following meaning:

⁽¹⁾ means 1,2,4-triazol-1-yl ⁽²⁾ means imidazol-1-yl ⁽³ > means 8: 4 ethyl acetate / hexane ⁽⁴⁾ means 40: 1 ethyl acetate / ethanol ⁽⁵⁾ represents ^a cyclopropyl C3H5 ^(sl represents the diastereomeric mixture was separated by thin layer chromatography: diastereomer A has diastereoisomer A: R _t = 0.3 (A symer has diastereomer B: Rf = 0.4 (EtOAc / hexane 6 : 4).

Diastereomer B can be recrystallized and has a melting point of 91-92 ° C.

TABLE I

Example R Ri Az _Rf, mp ° C 2.1 H 1-C3H7 Tr ' ⁴ ' 121 2.2 CHs 1-C3H7 Tr 98 to 99 2.3 CH3 1-C3H7 Im ⁽²⁾ 180 2.4 G & H5 1-C3H7 Tr 71 2.5 C6H5 1-C3H7 Im 188 2.6 CeHs t-C 6 H 8 Tr R _f = 0.35 ^'3' 2.7 C6H5 t-C 6 H 8 Im R _f = 0.35 ⁽⁴⁾ 2.8 CHs t-C 6 H 8 Tr 99 2.9 CH3 t-C 6 H 8 Im 2.10 n-C < H9 t-C 6 H 8 Tr 77 to 78 2.11 n-CaHg t-C 6 H 8 Im 2.12 n-C6H9 1-C3H7 Tr 65 2.13 n-C4H9 1-C3H7 Im 2.14 4-C1-CeHa t-C 6 H 8 Tr 125 to 127 2.15 4-C1-CeHa t-C 6 H 8 Im 158 2.16 4-F-C 6 H 4 1-C3H7 Tr 150 2.17 4-F — CeHa 1-C3H7 Im 2.18 4-CH ₃ O-CEHA 1-C3H7 Tr 132 to 133 2.19 4-CH3O-CeHa 1-C3H7 Im 175 to 176 2.20 4-CH3O-CeHa t-C 6 H 8 Tr 140 2.21 4-CH3O-CeHa t-C 6 H 8 Im 142 to 143 2.22 4-C1-CeHa 1-C3H7 Tr 129 2.23 CeHs CH 2 —CH (CH 3) 2 Tr 119 2.24 C6H5 CH (CH 3) - CH (CH 3) 2 Tr 97 2.25 CeHs C (CH 3) 2 - CH (CH 3) 2 Tr 2.26 CH3 CH 2 - CH (CH 3) 2 Tr 2.27 CH3 CH (CH3) —CH (CH3) -, Tr 117 2.28 CH3 C (CH 3) 2 —CH (CH 3) 2 Tr 2.29 t-C 6 H 8 1-C3H7 Tr 198 2.30 t-C 6 H 8 t-C 6 H 8 Tr 268 to 269 2.31 n-C6H9 CH 2 —CH (CH 3) 2 Tr 66 2.32 4-NO2 — CeHa t-C 6 H 8 Tr 227 2.33 CeHs CH (CH3) - C3H5 (15 ⁾ Tr (6) 2.34 CeHs I-C3H7 Tr 83 to 84 (R — C = C in m position) 2.35 CeHs CH 2 CH 3 - C 3 H 5 Im 139 (diastereomeric mixture) 2.36 4-F — CeHa t-C 6 H 8 Tr 122 2.37 CeHs cyclopropyl Tr 126 2.38 H cyclopropyl Tr 88 2.39 n-C6H9 cyclopropyl Tr R ₍₌ 0.35 (ethyl acetate / hexane 6: 4) 2.40 CeHs C (CH 3) 2 CH 2 CH = CH 2 Tr R _f = 0.45 (toluene / ethyl acetate

: 4), m.p. 58-60

Example 3

2- (4-Bromoethynylphenyl) -3,3-dimethyl-1- (1H-1,2,4-triazol-1-yl) butan-2-ol

2 g of bromine are added to 10 ml of a 2.5 N aqueous sodium hydroxide solution, and then a solution of 2.7 g of 2- (4-ethynylphenyl) -3,3-dimethyl-1- (1H-1,2,4-triazol-1-yl) butan-2-ol in 20 mL dioxane. The reaction mixture is kept at room temperature for three hours, then diluted with 100 ml of water and extracted with diethyl ether. The ether solution was washed with water, dried and the solvent was evaporated. The residue was crystallized from toluene-hexane to give colorless crystals of melting point 138 ^C C (R _f = 0.4, the system ethyl acetate / hexane 6: 4]. Example 4

Similarly to Example 2, the following compounds of formula I are obtained, wherein X is hydrogen and the group R - C = C - is in paraposition from the corresponding compounds of formula Ic.

Example R

4.1 ** Cl 4.2 Cl 4.3 J 4.4 Br

Ri Az _Rf, mp ° C t-C 1 H 8 Tr 45 to 46 I-C3H7 Tr I-C3H7 Tr 122 I-C3H7 Tr 197

Tr means 1,2,4-triazol-1-yl ** means contaminated with 30% of the perchloro compound

Example 5

2- (4-Chloroethylphenyl) -3-methyl-1- (1H-1,2,4-triazol-1-yl) butan-2-ol

To a stirred mixture of 12 g of 2- (4-ethyl-3-methyl-1- (1H-1,2,4-triazol-1-yl) butan-2-ol in 50 ml of hexamethylphosphoric acid as triamod is added portionwise 24.8 g of N-chlorosuccinimide over 15 minutes The reaction is slightly exothermic (the reaction temperature rises from 20 to 30 ° C) The reaction mixture is slightly cooled, maintaining the reaction mixture temperature at 25 to 30 ° C and stirred for 30 minutes. for one hour.

The bright yellow reaction solution was poured into 1000 mL of water and extracted with diethyl ether. The ethyl ether phase was washed once with water, dried and the solvent was evaporated. The oily residue is chromatographed on a silica gel column using toluene / ethyl acetate 3: 7 to give the title compound are obtained in an impure form _(Rf = 0.35).

Example 6

Method for the preparation of 2- (4-iodoethylphenyl) -3-methyl-1- (1H-1,2,4-triazol-1-yl) butan-2-ol

To a solution of 5.1 g of (2- (4-ethynylphenyl) -3-methyl-1- (1H-1,2,4-triazol-1-yl) hutan-2-ol) in 100 ml of absolute methanol is added simultaneously with Stirring at 20-25 ° C 2.6 g of iodine and 10 ml of 30% sodium hydroxide solution The reaction mixture is kept at room temperature for 24 hours with stirring, then poured into 500 ml of water and extracted with dichloromethane. The residue was stirred in the hexane fraction and left to stand for 16 hours, and the precipitate was filtered off with suction and dried to give the title compound, m.p. 122 ° C, as colorless crystals.

Example 7

Process for preparing 2- [4- (phenyl-9-ynyl) phenyl] -3-methyl-1- (1H-1,2,4-triazol-1-yl) butan-2-ol-methyl ether

Sodium hydride (1.6 g, 80%) was stirred in 60 mL of absolute dimethylformamide and then added dropwise over 60 minutes to a solution of compound 2.4 (16.6 g) in 60 mL of dimethylformamide at room temperature; the mixture was stirred for 30 minutes. Methyl iodide (7.4 g) was added to the mixture. The mixture was stirred for 15 hours at room temperature and then diluted with water; the solid was filtered off with suction, washed with water and dried to give 2- [4- (phenylethynyl) phenyl] -3-methyl-1- (1H-1,2,4-triazol-1-yl) butane -2-ol-methyl ether of melting point 181 DEG C. (petroleum ether; colorless crystals), R ₍₌ 0.6 (system trichlormethanjmethanol 95: 5).

Example 8

Fungicidal action

8.1. Combating powdery mildew

Erysiphe graminis-treated wheat is treated with a spray liquid containing the compound of Example 2.4 as an active ingredient at a concentration of 300 mg / l spray liquid. The application rate is 500 l / ha. The treatment results in a significant reduction in powdery mildew infestation.

8.2 Combating rust on wheat

The yellow rust of Puccinia striformis is treated with a spray liquid containing the compound of Example 2.4 at an active compound concentration of 100 mg / l spray liquid. A spray rate of 1000 l / ha is applied. The treatment results in a significant reduction of rust attack.

Claims (4)

Subject Fungicidal plant protection product, characterized in that it contains, as active substance, α-aryl-1H-azole-1-ethanol derivatives of the general formula I R-C = C oz C-CH,> ~ Az i ⁴ r ₄ (where R O represents hydrogen, halogen, alkyl of 1-5 carbon atoms, phenyl popříp. Substituted by halogen, alkoxy having 1 to 5 carbon atoms or nitro; R 1 is C 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 3 -C 6 cycloalkyl or C 3 -C 6 cycloalkylalkylene in the cycloalkyl moiety and C 1 -C 3 alkylene, Az 1,2,4-triazol-1-yl or imidazol-1-yl a Z is hydrogen or alkyl of 1 to 5 carbon atoms, in free form or in the form of acid addition salts. 2. A fungicidal composition according to claim 1, wherein the active ingredient is a compound of formula (I) wherein R, R1 and Az are as defined in (1), Z is hydrogen in free form or in acid addition salts. 3. A process for the preparation of an active ingredient according to claim 1, which comprises reacting an oxirane of formula II of the invention wherein R and R1 are as defined in claim 1 or a halohydrin derivative thereof, with a heterocyclic compound selected from the group consisting of 1,2, 4-triazole or imidazole, optionally in a compound of formula I wherein R 1 and Az are as defined in 1 and R and Z are hydrogen, replace the hydrogen atom of the ethynyl group with a halogen atom, and optionally obtain the ethanol compound of formula I, wherein R, Rt and Az are as defined in 1 and Z is hydrogen, etherified by reaction with a C 1 -C 5 alkyl halide to give a compound of formula I in free form or in acid addition salt form. 4. A process for the preparation of an active compound according to claim 3, which comprises reacting an oxirane of the formula II wherein R and Rt are as defined in item 1 or a halohydrin derivative thereof with a heterocyclic compound selected from the group consisting of 1,2,4 -trtazole or imidazole, optionally in a compound of formula I wherein R 1 and Az are as defined in 1 and R and Z are hydrogen, replace the hydrogen atom of the ethynyl group with a halogen atom to form a compound of formula I wherein R, R 1 and Az is as defined in item 1, Z is hydrogen, in free form or in acid addition salt form. Severography, n. Race 7, Most Price 2,40 Kčs