JPH07508736A - Triazolyl ethanol derivative - 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] Triazolyl ethanol derivative The present invention provides a novel triazolyl ethanol derivative, a method for producing the same, and a method for sterilizing and killing the same. For use as fungicides.

It is known that certain triazolylethanol derivatives have bactericidal and fungicidal properties. (German Patent Application No. 2,832.234 and German Patent Application No. 3゜002.430) reference). Thus, for example, in order to control fungi and fungi, 1. 1.　 1-Trichloro-3-(1,2,4-triazol-1-yl)-4-(2,4- dichlorophenyl)-butane-2,4-diol and 1. 1. 1-1-black Rollo 3-(1,2,4-)riazol-1-yl)-5,5-dimethyl-hexyl Sun-2,4-diol may be used. The action of these substances is good, but low There is room for improvement in many cases at low application rates.

formula In the formula, A represents a keto group or a CH(OH) group, and R represents a halogenoalkyl or represents halogenoalkenyl, and represents a group of, where X is halogen, alkyl having 1 to 4 carbon atoms, 1 to 4 carbon atoms and halo Halogenoalkyl having 1 to 5 carbon atoms, alkyl having 1 to 4 carbon atoms xy, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 halogen atoms , alkylthio having 1 to 4 carbon atoms, 1 to 4 carbon atoms and halogen atoms halogenoalkylthio having 1 to 5 carbon atoms, cycloalkylthio having 3 to 7 carbon atoms cyano, phenyl optionally substituted with halogen or optionally halogen represents phenoxy optionally substituted with m represents the number 0.1.2 or 3, or R1 is the formula %formula% )(+, )(2, X3 and x4 are the same or different, and hydrogen or halogen represents the Novel triazolylethanol derivatives and their acid addition salts and metal salt complexes have been discovered. I was taken out.

Compounds of formula (I) contain at least two asymmetrically substituted carbon atoms and are therefore photosensitive. It can be obtained in the form of chemical isomers. The invention relates to isomer mixtures and individual isomers. Concerning both.

Also triazolylethanol derivatives of formula (I) and acid addition salts and metal salt complexes thereof. body is expression In the formula, R1 has the above meaning, In the presence of a diluent and a catalyst, a triazolyl-butanone derivative of the formula In the formula, R has the above meaning, and optionally the resulting formula in which R and R1 are A triazolylethanol derivative having the following meaning: α) react with a complex hydride in the presence of a diluent; or β) in the presence of a diluent. is either reacted with aluminum isopropylade and the resulting If the compound of formula (I) is subsequently subjected to an addition reaction optionally with an acid or metal salt, It was found that this can be obtained.

Finally, novel triazolylethanol derivatives of formula (I) and their acid addition salts and It has been found that metal salt complexes have extremely good bactericidal and fungicidal properties.

Surprisingly, the substance according to the invention (with respect to structure number 2, the closest pz of the same kind) It has better bactericidal and fungicidal properties than conventional compounds. full Ii, original With regard to its bactericidal and fungicidal properties, the substances according to 1, 1. which are structurally similar compounds. 1-to1-chloro-3-nyl)-butane- 2,4-diol and l,l,1-1-'fuchloro-3--2,4-diol Overcome L%.

Furthermore, other active compounds in the novel triazo-1-norethanol protection of formula (I) The key to manufacturing things! It is a j intermediate. file (f, these substances are Corresponding ether, acyl or carbamoyl derivatives by reaction with the roxyl group can be converted into Keto radicals (substances of formula (I) present are reacted with carbonyl functional groups) can be converted into oximes, oxime ethers, hydrazones and ketals by

General definition of triazolylethanol derivatives according to the invention (formula (I)) available.

A represents a keto group or a C,H (OH) group, R('! Preferably 1 carbon atom 1 to 10 atoms and) 10 atoms with 1 to 5 atoms (branched chain atoms) rogenoalkyl (or mo): 2 to 10 carbon atoms and 1 halogen atom Represents a 10genoalkenyl having ~5.

R+ is the formula represents a group of kill, 1 or 2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms halogenoalkyl having 1 to 3 carbon atoms, alkoxy having 1 to 3 carbon atoms, or 2 fluorine, chlorine and/or bromine atoms and 1 to 5 fluorine, chlorine and/or bromine atoms. koxy, alkylthio having 1 to 3 carbon atoms, 1 or 2 carbon atoms and Halogenoalkylthio, carbon having 1 to 5 fluorine, chlorine and/or bromine atoms Cycloalkyl having 3 to 6 atoms, cyano, optionally fluorine, chlorine and/or odor phenyl optionally substituted with 1 to 3 substituents of the same or different fluorine, chlorine and/or bromine, or as appropriate represents phenoxy which may be substituted with 1 to 3 different substituents, and m is 0 , represents the number 1, 2 or 3. If m represents 2 or 3, the meaning of X is the same Or it could be something different.

R1 is in addition the formula represents a group, where XI, X2, X3 and X4 are the same or different, and Preferably it represents hydrogen, fluorine or chlorine.

Particularly preferred substances are those in which A again represents a keto group or a CH(OH) group and R is particularly preferred. Preferably, it has 1 to 5 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms. represents a straight-chain or branched halogenoalkyl, or a carbon atom of 2 5 and 1 to 5 fluorine, chlorine and/or bromine atoms and R1 is again of the formula represents a group in which X is particularly preferably fluorine, chlorine, bromine, methyl, ethyl , trifluoromethyl, trichloromethyl, difluoromethyl, difluorochloro lomethyl, methoxy, ethoxy, trifluoromethoxy, trichloromethoxy, Difluorochloromethoxy, difluoromethoxy, methylthio, ethylthio, Lifluoromethylthio, trichloromethylthio, difluoromethylthio, cyclo Propyl, cyclopentyl, cyclohexyl, cyano, optionally fluorine and/or Phylphenates which may be mono- or di-substituted with the same or different substituents consisting of chlorine. phenyl, or optionally the same or the same group consisting of fluorine and/or chlorine. represents phenoxy which may be mono- or di-substituted with different substituents, and m is also particularly preferably the number 0.1.2 or 3 and m is 2 or 3. , X represents the same or different groups, R1 is additionally represented by the formula in which Xl is particularly preferably hydrogen or fluorine and X2 is Particularly preferably represents fluorine, and X3 particularly preferably represents hydrogen or fluorine. and X4 particularly preferably represents fluorine.

Other suitable substances according to the invention are acids and A, R and R1 are listed above as preferred. Addition products of triazolylethanol derivatives of formula (I) and acids having the meaning given above It is.

Acids that can be used for the addition preferably include hydrohalic acids such as hydrochloric acid and hydrobromic acid. , especially hydrochloric acid, as well as phosphoric acid, nitric acid, sulfuric acid, - and trifunctional carboxylic acids and hydrochloric acids Carboxylic acids such as acetic acid, maleic acid, succinic acid, fumaric acid, tartaric acid, citric acid , salicylic acid, sorbic acid and lactic acid, and sulfonic acids such as p-) fonic acid, 1,5-naphthalenedisulfonic acid or camphorsulfonic acid, and Contains saccharin and thiosaccharin.

Substances according to the invention which are also suitable are those of the main groups 1 to 2 of the periodic table of the elements as well as I, Salts of metals from the subgroups A, R and R1 are listed above as preferred. Addition products with triazolylethanol derivatives of formula (I) having meaning.

In this connection, copper, zinc, manganese, magnesium, tin, iron and nickel Particular preference is given to salts. Suitable anions for these salts are physiologically acceptable acid additions. It is derived from the acid that gives rise to the product.

Particularly suitable such acids in this connection are hydrohalic acids such as hydrochloric acid and hydrogen bromide. acids, and also phosphoric acid, nitric acid and sulfuric acid.

Examples of substances according to the invention include the triazolylethanol derivatives shown in the following table: .

Table 1 Table 1 - System Table 1 - System Table 1 - System Table 2 Table 2 - System Table 2 - continued 2,2-dimethyl-1-(4-trifluoromethylthiophenyl )-4-(1,2,4-1-riazol-1-yl)-butan-3-one and When using loral as well as sodium methylate as catalyst, the process according to the invention The route can be represented by the following formula: 1. as starting materials. 1. 1-trichloro -2-hydroxy-3-(1゜2.4-triazol-1-yl)-5,5-dimethyl thyl-6-(4-1-lifluoromethylthiophenyl)-hexan-4-one and When sodium borohydride is used as the reducing agent, the second step of the process according to the invention The process can be represented by the following equation: The triazolyl group required as starting material for carrying out the process according to the invention A general definition of tanone derivatives is given by formula (II). In this formula, R1 is preferably for this substituent in connection with the description of the substances of formula (I) according to the invention. has the meaning already given as preferred.

The triazolyl-butanone derivatives of formula (n) are known or in principle can be It can be produced by known methods (German Patent Application No. 3 048.267). and European Patent Application Publication No. 0.226.916).

Also of the aldehydes required as starting materials for carrying out the process according to the invention. A general definition is given by the formula (I[[). In this formula, R is preferably The considerations already mentioned as preferred in connection with the description of the substances of formula (I) according to the invention Has taste.

Aldehydes of formula (III) are generally known compounds of organic chemistry.

The catalysts which can be used for carrying out the first step of the process according to the invention are those customary for such reactions. All reaction accelerators used. Preferred are alkali metal hydroxides such as hydroxyl sodium or potassium hydroxide, as well as alcoholades such as sodium methylate and potassium t-butylade, and also salts such as titanium tetrachloride and Sodium acetate.

Diluents suitable for carrying out the process according to the invention (first step) are all commonly used inert diluents. It is an organic solvent. Preferably used include halogenated hydrocarbons such as salts. methylene chloride, chloroform or carbon tetrachloride, and also ethers such as diethyl ether, dioxane or tetrahydrofuran, and also carboxylic acids such as vinegar Acids, especially glacial acetic acid.

When carrying out the process according to the invention (first step), the reaction temperature can be varied within a certain range. Ru. It is generally carried out at temperatures between 10 and 120°C, preferably between 20 and 100°C.

When carrying out the method according to the invention, the first step and any subsequent steps are carried out under atmospheric pressure. The second step, which can be carried out in both cases, is normal.

For carrying out the process according to the invention, per mole of triazolyl-butanone derivative of formula (n) Generally, 1 to 1.3 moles of aldehyde of formula (III) and a catalytic amount of reaction accelerator are added. Needed. Treatment is carried out by conventional methods. Add water to the reaction mixture and separate the organic phase. , drying this and concentrating under reduced pressure is a common method.

When carrying out the process according to the invention, the triazolyl of formula (Ia) initially formed The ethanol derivative is converted into a complex hydride (modification α) or a complex hydride in the second step as necessary. can be reduced using aluminum isopropylade (modified β).

Complex hydrides suitable for carrying out the second step of the process according to the invention (process variant α) are preferably are sodium borohydride and lithium aluminum hydride.

Diluents suitable for carrying out the second step of the process according to the invention (process variant β) are always suitable for such reactions. All inert organic solvents used. Examples of alcohol that can be used suitably For example, methanol, ethanol, isopropanol or butanol, and also -ethers such as diethyl ether or tetrahydrofuran, or also alcohols There is water in a mixture with water.

When carrying out the second step of the process according to the invention (variant α), the reaction temperature is within a certain range. It can be changed with Generally carried out at a temperature between -20 and 80°C, preferably between 0 and 60°C. cormorant.

The second step (variant α) of the process according to the invention is carried out using a triazolyl ether of the formula (Ia). It is generally necessary to use an equivalent amount or even an excess of complex hydride per mole of nor derivative. Essential. Treatment is carried out by conventional methods. Concentrate the reaction mixture and add water to the remaining residue. , followed by multiple extractions with organic solvents with low miscibility with water, and the combined organic phase was dried. , and concentrating this is a common method.

Diluents suitable for the second step of the process according to the invention (process variant β) are those commonly used in such reactions. All inert organic solvents. Alcohols, such as alcohols, can be preferably used. Sopropatol and also aromatic hydrocarbons such as benzene.

Also, during the implementation of the second step of the process according to the invention (process variant β), the reaction temperature is varied over a relatively wide range. Can be changed to range. generally between 20 and 120°C, preferably between 50 and 100°C Do it at temperature.

The second step (variant β) of the process according to the invention can be carried out using a doriazolyle ether of the formula (Ia). Generally an equivalent amount or even an excess, preferably 1 to 2 moles, per mole of tanol derivative. Requires the use of aluminum isopropylade. Processing is done using conventional methods. . Concentrate the reaction mixture, then add dilute mineral acid or aqueous alkali metal base, then Extraction is carried out using an organic solvent with low miscibility with water, the combined organic phases are dried and Concentrating the levers is a common method.

The triazolylethanol derivatives of formula CI) according to the invention are acid addition salts or metal salts. Can be converted into complexes.

Acids suitable for the preparation of acid addition salts of compounds of formula (I) are preferably acid addition salts according to the invention. Those already mentioned as suitable acids in connection with the description of the salts.

An acid addition salt of a compound of formula (I) can be prepared by, for example, adding a compound of formula (I) to a compound of formula (I) by a conventional method of ring formation. easily obtained by dissolving in a suitable inert solvent and adding an acid such as hydrochloric acid can be isolated by known methods, e.g. by filtration, and if necessary Purification can be carried out by washing with an inert useful solvent, if appropriate.

Metal salts suitable for the preparation of metal salt complexes of compounds of formula (I) are preferably those according to the invention. Suitable metal salts are those already mentioned in connection with the description of metal salt complexes.

The metal salt complex of the compound of formula (I) can be prepared by a conventional method, for example, by mixing the metal salt with an alcohol, e.g. Simply by dissolving in ethanol and adding the solution to the compound of formula (I) Obtainable. The metal salt complex can be isolated by known methods, e.g. by filtration. can be purified by recrystallization if necessary.

The active compounds according to the invention have a strong microbicidal action (microbicidal ac tion) and can be used as a bactericidal and fungicide.

A fungicide and fungicide for plant protection is Plasnodiofluoromycetes. phoromycetes), Oomycetes (Oomycetes), Chitolidio Mycetes (Chytridiomycetes), Zygomycetes etes), Ascoiycetes, Basidiomycetes ycetes) and Deuteromycetes Used when

Examples of disease-causing pathogens of fungi, molds, and bacteria included in the general fungi listed above. The following may be mentioned, but they are by no means limited to: : Xanthomonas species such as Xanthomonas ori Xanthomonas oryzae; Pseudomonas doaonas) species such as Pseudomonas lacrimans as1achry■ans);Erwinia species such as Erwinia amylovora: Pythium (Pythium) species such as seedling damping-off (Pythium ultimum); Phytophthora species such as phytophthora ora 1nfestans); Pseudomonaspora (Pseudopero nospora) species such as downy mildew (Pseudoperonospora hu muli or Pseudoperonosp.

ra cubense); Plasmopara species, e.g. Mildew (Plasmopara viticola); Peronospora (Pero nospora) species such as downy mildew (Per.

nospora pisi or P, brassicae): Erysihue ( Erysiphe) species such as powdery mildew (Erysiphe graminis) ): Sphaerotheca species such as powdery mildew (Sp haerotheca fuliginea); Podosp haera) species such as powdery mildew (Podosphaera 1eucotri) i:ha); Venturia species such as Ventu ria 1 naequalis); Pyrenophora species For example, Pyrenophora teres or P. gramin ea) (Conidial type: Drechslera, synonym: Be1w1nth osporiua +); Cochliobolus species illustration Cochliobolus 5ativus (conidial type: Drechslera, synonym: He1a + inthosporium); Romyces (Uroa+yces) species such as Uromyces appe Puccinia species such as Fusarium rust (P. ndiculatus); Uccinia recondita) ; Fusube genus (Ti11etia) species For example, Tilletia caries; ilago) species such as Ustilago nuda or Ustil Ago avenae); Pellicularia species example For example, sheath blight (Pelicularia 5asakii); (Pyricularia) species such as rice blast (Pyricularia or yzae) ; Fusarium species such as Fusarium cul Fusarium culmorum; Botryt iS) species such as botrytis cinerea; Septoria species such as Septoria nodorum ; Leptosphaeria species such as Leptosphaeria A nodorum (Leptosphaeria nodorum); Cercospora Cercospora species such as Cercospora canescens ora canescens) ; Alternaria (^1ternaria) species For example, black spot (^1ternaria brassicae) and Cosporella (Pseudocerc.

5porella) species such as Busoidcercosporella herpotrichoides (P seudocercosporella herpotrichoides).

The active compounds according to the invention are used in particular for rice blast disease (Pyricularia). oryzae) and sheath blight (Pellicularia 5asakii). and cereal diseases such as Leptosphaeria nodorum (Leptosph aeria nodoru II), Spot disease (Cochliobolus 5at) Pyrenophora teres), Pyrenophora teres, Pyrenophora teres Pseudocercosporellah erpotrichoides), Erysiphe and Fu Suitable for controlling Fusariu+m species. Furthermore, according to the present invention Substances are Venturia, Uncinula , Sphaerotheca and gray mold @ (Botry tis).

Furthermore, they have broad in vitro activity.

The substances according to the invention can be used in conventional compositions, for example solutions, emulsions, suspensions, powders, capsules, Very fine capsules and coats in polymeric materials for liniments, granules, aerosols and seeds. ting compositions, as well as ULV compositions. These compositions are In known methods, for example, the active compound is liquefied under pressure in an extender, ie a liquid solvent. a gaseous and/or solid carrier and optionally a surface-active agent, i.e. an emulsifier and/or an emulsifier. Manufactured by mixing with powder and/or foaming agent. Also, when water is used as an extender, In this case, it is also possible, for example, to use organic solvents as auxiliary solvents. As a liquid solvent, mainly Aromatic hydrocarbons such as xylene, toluene or alkylnaphthalenes, salts hydrogenated aromatic or aliphatic hydrocarbons such as chlorobenzene, chloroethyl or methylene chloride, aliphatic hydrocarbons such as cyclohexane, or paraffin mineral oil fractions, alcohols such as butanol or glycols, and ethers and esters of ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, or strong polar solvents such as dimethyl Chilformamide and dimethylformoquinde and water are suitable. liquefied air Body extender or carrier means a liquid that is a gas at normal temperature and pressure, e.g. halogenated hydrocarbons and such as butane, propane, nitrogen and carbon dioxide It is an aerosol propellant base. As a solid carrier, ground natural minerals such as ca Phosphorus, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth as well as ground synthetic minerals such as highly dispersed silicic acid, Luminas and silicates are suitable. As a solid carrier for granules, crushed and Separated natural rocks such as calcite, marble, pumice, sepiolite and dolomite and inorganic and organic ground synthetic granules and granules of organic substances such as sawdust, coconut, and tortoise. Corn cobs and tobacco stalks are suitable. Non-use as emulsifier and/or blowing agent Ionic and anionic emulsifiers such as polyoxyethylene-fatty acid esters, polymers, Lioxyethylene aliphatic alcohol ether e.g. alkylaryl polyglyco ether, alkyl sulfonate, alkyl sulfate, nates as well as albumin hydrolysis products are suitable.

Suitable dispersants are, for example, lignin sulfite waste liquor and methylcellulose. There is.

Adhesives such as carboxymethylcellulose and natural powders, granules or grids and synthetic polymers such as gum arabic, polyvinyl alcohol and polyvinyl acetate. tate and natural phospholipids, such as cephalins and lectins, and synthetic phospholipids. can be used in the composition. Other additives can be mineral oil and vegetable oil. Ru.

Colorants such as inorganic pigments such as iron oxide, titanium oxide and Prussian blue; Organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and Trace nutrients such as iron, manganese, boron, copper, cobalt, molybdenum and zinc salt can be used.

The preparations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%. Contains between % by weight.

Are the active compounds according to the invention other known active compounds? Ie(f bactericidal/moldicide, killing Insecticides, acaricides and insecticides It can be present as a herbicide, as well as a mixture with fertilizers and growth regulators.

The active compounds may be present as such, in the form of their preparations or 1. )+1 prepared from the preparation Use forms such as prepared solutions, emulsifiable concentrates, emulsions 1, foams, suspensions, It can be used in the form of wettable powders, liniments, soluble powders, dusts and granules. child These items can be treated using normal methods (1, 1, 1, 1, 2, 3, 4, 5, 6, 7, 8). ging, granule dispersion, powder dispersion, foaming, brushing, etc. applied by. Additionally, the active compound may be applied according to the ultra-low volume method1 or Alternatively, preparations of the active compound or the active compound itself can be injected into the soil. Ru. It is also possible to treat plant seeds.

When using the substances according to the invention, the application rates are relatively wide depending on the nature of the application. It can be changed within the range. For example, in the treatment of plant parts, in the application form The active compound concentration is generally between 1 and 0,000% by weight, preferably between 0 and 0% by weight. ．． 0.001% by weight. For seed treatment, use LN at 0.00 g per 1 seed. An amount of active compound of from 1 to 509, preferably from 0.01 to 109 is generally required. Ru. If based on soil treatment ζ2, 0.00001 to 0.1% by weight, preferably 0 ．． Active compound concentrations of 0.0001 to 0.02% by weight are required at the site of action.

The preparation and use of the substances according to the invention are evident from the following examples.

Chloral 7, 0 g (0.48 mol) was added to diethyl ether while stirring at room temperature. 2,2-dimethyl-1-(4-)lifluoromethylthiophenyl in 80 ml of ) -4-(1,2,4-triazol-1-yl)-butan-3-one 15, O g (0,0437 mol) and sodium methylate 0.38 g (0,007 mol) was added dropwise to the solution. The reaction mixture was heated under reflux for 5 hours, then Added water. Separate the organic phase, dry over sodium sulfate and concentrate under reduced pressure. did. In this method, 1.1°1-1-cyclo-2-hydroxy-3-(1,2, 4-) Riazol-1-yl)-5,5-dimethyl-6-(4-)lifluoromethi 17.3 g (80.7% of theory) of the oil Obtained as follows.

'HNMR(CDC]3/TMS); δ=1.60ppm 0.42ppm 1.61ppm 0.79ppm Solution of 0.4 g (0,0017 mol) of sodium borohydride in 10 ml of water 1.1.1-Trichloro-2-hydrogen in 80 ml methanol with stirring at room temperature. Droxy-3-(1,2,4-triazol-1-yl)-5,5-dimethyl-6 -(4-trifluoromethylthiophenyl)-hexan-4-one 14.2g (0,029 mol) dropwise. The mixture was stirred at room temperature for 1 hour. , then the solvent was removed by distillation. Add water to the residue and salify the resulting mixture Extracted several times with methylene. - Dry the combined organic phases over sodium sulfate and Concentrate under reduced pressure by removing the solvent. Dissolve the remaining residue in diisopropylene It was recrystallized from ether. In this method, 1.1.1-trichloro-3-(1,2°4 -triazol-1-yl)-5,5-dimethyl-6-(4-)lifluoromethyl thiophenyl)-hexane-2,4-diol 4.4 g (30.9% of theory) was obtained in the form of a solid substance with a melting point of 110°C.

Compounds of formula (I) shown in Table 3 below were also prepared by the above method.

Table 3 3 4-C1Co-CCl3 melting point = 158'C4<-r CO-CC13 melting point =142'C53,4-C1-, Co-CC13 melting point = 162°C64-CI CH(OH) -CCI3 Melting point M169°C74-F CH(01(+- CCI3 melting point' IS5'CB =, a-c12CH(OH) -CC13 melting point Point 11176'C114-CF Co-C (-13 melting point -169'C-z3 5-CH3Co = CCl3 Melting point = 1690C Once in the bag (continued) 17 4-Br Co-CC13 melting point = 178°C184-CF3 Co- CHC126=1-29 ppm T6H1'19 3.4-C12Co-C CI2-CH2Cl　Fp　=　1556C204-C1F2Co　Co　-C CI2-CH2Cl Melting point: 145°C227l-C1F2Co CHCOK) -CCI3 Melting point 21753 25 4-CF3CO (01-11-CCI3 Melting point = 168°C26ll-CH5CH (OHI-CCI3 Melting point 2172 80 Table 3 (continued) 28 4-CI Co-CCI2-CH2C1 melting point=159°C2”+4 -CF3-5-CO-CCI2-CM2C1 melting point = 158°C304Br　CH (OH) -CC13 melting point = 171'C: +1 4-CF--5-Co-CH C1215=1.28I) I'+II+ ((IH)'34 3.4-Cl2C H(OH) -CCI2-CH2-CI Melting point 1666C364-CF3-0 -Co -L; C13 melting point; 172°C3B 4-CF3-0-Co -CCI 2-C) I2C1 melting point = 153°C Table 3 (continued) 40　4-F　Co　-CCI3　Melting point; 165°C414-F　Co　-CC 12-CH-CH3 melting point = 161'C424-F Co-CCI2-CH2 -C1 melting point = 172°C434-CF30- CI(OH) -CCI2-CM -CH3 melting point = 162°C ■ 44 4-CFcoO-CH(OH)-CCI3 Melting point=136°C454-F CH(OHI-CHCIM δ=i, 28ppm +6H1'46 4-C I CH(OH) -CC]2-CH2-C1 Melting point = 154°C474-FC )(fOHl-CCI melting point=163°C484-FCH(OHI-C CI2-CH-CH3 melting point = 151°C504-CF30- CH(OHI- CC12-CH2C1 melting point = 142°C51' 4-CF3-5-CH (OHI -CCIZ-C) (2C1 melting point 21468 mouths 52 4-CIF2C-0-CH (OHI-CCI2-CH2C1 melting point = 150°C zero) The given δ value is 'H In the zero-order usage example representing a signal from an NMR spectrum, the following material is used as a comparison material. A compound of the following formula was used: (from German Patent Application No. 3,002,430) Known) Example A Powdery Mildew (Erysiphe) Test (Barley)/Protection Medium: Dimethylform Amide 100 parts by weight Emulsifier: 0.25 parts by weight To prepare a suitable preparation of the active compound, 1 part by weight of the active compound is dissolved in the above amount. Mixed with vehicle and emulsifier, the concentrate was diluted with water to the desired concentration.

To test for protective activity, young plants are dripped with a preparation of the active compound. I sprayed it until it was completely wet. This plant has powdery mildew after the spray coating has dried. Spores of disease (Erysiphe graminis f, sp, hordei) sprinkled with

The plants are heated to a temperature of about 20°C and about 80°C to promote the development of powdery mildew ridges. % relative atmospheric humidity.

Evaluation was performed 7 days after inoculation.

The active compounds, active compound concentrates and experimental results appear from the table below.

Table A: Powdery Mildew Test (Barley)/Protection CI, 008 Ca1. OHO)I Example B Venturia test (apple)/protective solvent: acetone 4,7 Weight part Emulsifier: alkylaryl polyglycol ether 0. 3 parts by weight active compound To prepare a suitable preparation of the active compound, 1 part by weight of the active compound is added to the above amounts of solvent and milk. The concentrate was diluted with water to the desired concentration.

To test for protective activity, young plants are dripped with a preparation of the active compound. I sprayed it until it was completely wet. Apple black on conoplants after spray coating dries star pathogenic bacteria [apple 5 cab causative organicism ( An aqueous suspension of conidia of Venturia 1 naequalis) The seeds were seeded and then placed in a culture room for 1 day at 20° C. and 100% relative humidity.

The plants were placed in a greenhouse at a temperature of about 20° C. and a relative humidity of about 70%.

Evaluation was performed 12 days after inoculation.

The active compounds, active compound concentrations and experimental results appear from the following table.

Table B-1: Scotch blight test (apple)/Efficacy level of protective active compound, % −=0 (control) Example C Uncinula test (grape)/Protective solvent: Acetone 4 ．． 7 parts by weight Emulsifier: alkylaryl polyglycol ether 0.3 parts by weight active compound To prepare a suitable preparation, 1 part by weight of the active compound is combined with the above amounts of solvent and The concentrate was diluted with water to the desired concentration.

To test for protective activity, young plants are dripped with a preparation of the active compound. I sprayed it until it was completely wet. After the spray coating dries, the plants will be exposed to fungal and fungal infections. Conidia of Uncinula necator sprinkled.

The plants were placed in a greenhouse at about 23-24° C. and about 75% relative atmospheric humidity.

Evaluation was performed 14 days after inoculation.

The active compounds, active compound concentrations and experimental results appear from the following table.

Table C: Bovine Sinura Test (Grapes)/Protection This Description and Examples Illustrate the Invention or other information relating to the concept and scope of the invention, which is not intended to limit the invention, and which is related to the concept and scope of the invention. It should be noted that specific examples are obvious to those skilled in the art.

Continuation of front page (72) Inventor Deutsmann, Stefan Day of the Federal Republic of Germany - 4010 Hilden Kosenberg 10 (72) Inventor: Dene, Weinz Wilhelm Day-401 of the Federal Republic of Germany 9 Monheim Krischer Strasse 81

Claims (1)

[Claims] 1. formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼In formula (I), A is a keto group or CH(OH) represents a group, R represents halogenoalkyl or halogenoalkenyl, and R1 is the formula ▲Contains mathematical formulas, chemical formulas, tables, etc.▼ represents the base of X is halogen, alkyl having 1 to 4 carbon atoms, 1 to 4 carbon atoms and halo Halogenoalkyl having 1 to 5 carbon atoms, alkyl having 1 to 4 carbon atoms xy, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 halogen atoms , alkylthio having 1 to 4 carbon atoms, 1 to 4 carbon atoms and halogen atoms halogenoalkylthio having 1 to 5 carbon atoms, cycloalkylthio having 3 to 7 carbon atoms cyano, phenyl optionally substituted with halogen or optionally halogen represents phenoxy optionally substituted with m represents the number 0, 1, 2 or 3, or R1 is the formula ▲Contains mathematical formulas, chemical formulas, tables, etc.▼ represents the base of X1, X2, X3 and X4 are the same or different and contain hydrogen or halogen represent, triazolylethanol derivatives and their acid addition salts and metal salt complexes. 2. A represents a keto group or a CH(OH) group, and R has 1 to 10 carbon atoms and Represents a straight-chain or branched halogenoalkyl having 1 to 5 halogen atoms. Watermelon or halogenoas having 2 to 10 carbon atoms and 1 to 5 halogen atoms Represents rukenyl, and R1 is a formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ represents a group of kill, 1 or 2 carbon atoms and 1 to 5 fluorine, chlorine and/or bromine atoms halogenoalkyl having 1 to 3 carbon atoms, alkoxy having 1 to 3 carbon atoms, or 2 fluorine, chlorine and/or bromine atoms and 1 to 5 fluorine, chlorine and/or bromine atoms. koxy, alkylthio having 1 to 3 carbon atoms, 1 or 2 carbon atoms and Halogenoalkylthio, carbon having 1 to 5 fluorine, chlorine and/or bromine atoms Cycloalkyl having 3 to 6 atoms, cyano, optionally fluorine, chlorine and/or Phenyl optionally substituted with 1 to 3 substituents consisting of bromine and the same or different substituents fluorine, fluorine and/or bromine, or as the case may be, the same or represents phenoxy which may be substituted with 1 to 3 different substituents, and m is represents the number 0, 1, 2, or 3, or R1 is a formula ▲ has a mathematical formula, chemical formula, table, etc. represents the group ▼ or ▲ where there are mathematical formulas, chemical formulas, tables, etc., where X1, X2, X3 and X4 are the same or different and represent hydrogen, fluorine or chlorine A triazolylethanol derivative of formula (I) according to claim 1. 3. A represents a keto group or a CH(OH) group, and R represents 1 to 5 carbon atoms and a fluoride group; linear or branched halo having 1 to 5 chlorine and/or bromine atoms; represents genoalkyl or has 2 to 5 carbon atoms and fluorine, chlorine and/or represents halogenoalkenyl having 1 to 5 bromine atoms, and R1 is of the formula ▲Contains mathematical formulas, chemical formulas, tables, etc.▼ represents a group, where X is fluorine, chlorine, bromine, methyl, ethyl, trifluoro Methyl, trichloromethyl, difluoromethyl, difluorochloromethyl, meth Oxy, ethoxy, trifluoromethoxy, trichloromethoxy, difluorochloro lomethoxy, difluoromethoxy, methylthio, ethylthio, trifluoromethyl ruthio, trichloromethylthio, difluoromethylthio, cyclopropyl, cyclopropyl Lopentyl, cyclohexyl, cyano, optionally consisting of fluorine and/or chlorine Represents phenyl optionally substituted with one or two substituents or optionally with the same or different substituents consisting of fluorine and/or chlorine. represents phenoxy which may be mono- or di-substituted, and m is 0, 1, 2 or or 3, and when m represents 2 or 3, X is the same or different Represents a group, or R1 is a formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, ▲ Numerical formulas, chemical formulas, etc. Represents the group ▼ or ▲ has mathematical formulas, chemical formulas, tables, etc. , where X1 represents hydrogen or fluorine, X2 represents fluorine, and X3 represents hydrogen. or represents fluorine, and X4 represents fluorine, according to claim 1. Triazolylethanol derivatives of formula (I). 4. at least one triazolyl ethanol of formula (I) according to claim 1; and/or triazolylethanol derivatives of formula (I). A fungicidal and fungicidal composition comprising an addition salt or a metal salt complex. 5. The triazolyl ester of formula (I) according to claim 1 for controlling fungi and capi Use of tanol derivatives and/or their acid addition salts and metal salt complexes. 6. The triazolyl ethanol derivative and/or the formula (I) according to claim 1 or its acid addition salts or metal salt complexes are applied to bacteria/molds and/or their habitats. A method for controlling bacteria and mold, which is characterized by: 7. Triazolyl ethanol derivatives and/or formula (I) according to claim 1 or its metal salt complexes or acid addition salts mixed with fillers and/or surface-active substances. A method for producing a bactericidal and fungicidal composition, characterized by: 8. formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼In formula (I), A is a keto group or CH(OH) represents a group, R represents halogenoalkyl or halogenoalkenyl, and R1 is the formula ▲Contains mathematical formulas, chemical formulas, tables, etc.▼ represents the base of X is halogen, alkyl having 1 to 4 carbon atoms, 1 to 4 carbon atoms and halo Halogenoalkyl having 1 to 5 carbon atoms, alkyl having 1 to 4 carbon atoms xy, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 halogen atoms , alkylthio having 1 to 4 carbon atoms, 1 to 4 carbon atoms and halogen atoms halogenoalkylthio having 1 to 5 carbon atoms, cycloalkylthio having 3 to 7 carbon atoms cyano, phenyl optionally substituted with halogen or optionally halogen represents phenoxy optionally substituted with m represents the number 0, 1, 2 or 3, or R1 is the formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲There are mathematical formulas, chemical formulas, tables, etc.▼ represents the base, here X1, X2, X3 and X4 are the same or different and contain hydrogen or halogen represent, to produce triazolylethanol derivatives and their acid addition salts and metal salt complexes. In some cases, the expression ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II) In the formula, R1 has the above meaning, In the presence of a diluent and in the presence of a catalyst, a triazolyl-butanone derivative of the formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼(III) In the formula, R has the above meaning, and optionally the resulting formula CH300H ▲There are mathematical formulas, chemical formulas, tables, etc.▼(Ia) In the formula, R and R1 have the above meanings. The triazolylethanol derivative of α) react with a complex hydride in the presence of a diluent; or β) in the presence of a diluent. is either reacted with aluminum isopropylate and the resulting a compound of formula (I), optionally with an acid or metal salt; Triazolylethyl derivatives of formula (I) and their acid addition salts and gold, characterized by A method for producing a genus salt complex.