DE2634511A1 - BETA-AZOLYL KETONE - Google Patents

Description

BASF Aktiengesellschaft

Our sign; OZ 32 114 Sws / St 6700 Ludwigshafen, July 28th, 1976

ß-Azoly! ketones

The present invention relates to new valuable β-azolyl ketones and their salts, processes for their preparation and their use as fungicides.

It is known that 1,2,4-triazole derivatives, for example 1- [1,2,4-triazolyl- (1 ) J -2- (4'-chlorophenoxy) - * !, M-dimethyl-pentan-3-one show good fungicidal effectiveness. (German Offenlegungsschrift 23 35 020). The effect of these substances is at low application rates and concentrations not satisfactory. In addition, its fungitoxic effect is high Phytotoxicity connected, so that in the concentrations necessary for combating rust fungi, the cultivated plants be harmed. For these reasons, they are not always suitable for use as pesticides to control fungi and not suitable for all types and types of grain.

It has been found that the new ß-azolyl ketones of the formula p ^ -CO-CH-CH-R ² (j)

in the

R alkyl with up to 5 carbon atoms, cycloalkyl and optionally substituted aryl,

2
R means furanyl, thiophenyl, naphthyl or phenyl, where the phenyl radical can be substituted by halogen, alkyl, alkoxy, alkenyloxy, nitro, trifluoromethyl and R and R do not mean phenyl at the same time, effective against harmful fungi, especially from the class of the Ascomycetes and Basidiomycetes are. R denotes, for example, methyl, isopropyl, tert-butyl, neopentyl, norbornyl, phenyl, p-chlorophenyl or 2,4-dichlorophenyl.

-2-

709865 / 04S2

R means, for example, phenyl, ToIyI, p-isopropyl-phenyl, Naphthyl, thienyl, puryl, m- and p-chlorophenyl, p-bromo-phenyl, 2,4-dichlorophenyl, 3, ^ - dichlorophenyl, p-methoxyphenyl, 3,5-dichloro - ^ - allyloxyphenyl, o-allyloxyphenyl, p-nitro-phenyl or p-trifluoromethyl-phenyl.

It has also been found that ß-azolyl ketones of the formula (I) or their salts are obtained if one o ^, ß-unsaturated ketones of formula

R ¹ -CO-CH = CH-R ² (II)

in which

1 2
R and R have the meaning given above, reacted with 1,2,4-triazole, if appropriate in the presence of a basic catalyst and if appropriate in the presence of a diluent. This preparation process is preferred. The compounds are also obtained if ß-IIalogenketones of the formula

R ^ CO-CH ₅ -CH-R ² (III) <= - ι
X

in which

1 2
R and R have the meaning given above and X is halogen, reacted with 1,2,4-TrIaZoI, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent. Finally, the compounds are obtained if ketones of the formula R-CO-CH (IV) and aldehydes of the

2 1?

Formula OCH-R (V) in which R and R are as given above Have meaning with 1,2,4-triazole, if appropriate in the presence a basic catalyst and, if appropriate, in the presence of a diluent. From the following these procedures The compounds obtained can be used to prepare the salts with acids.

The implementation of ^ »^" unsaturated ketones with 1,2, ^ according to the method described above is expedient without

-3-

703885/0452

- ι - OoZo 32 \\ Κ

Diluent or in an inert diluent, zobo methanol, ethanol, isopropanol, n-butanol, tetrahydrofuran, dioxane, toluene, xylene, dimethylformamide, at temperatures from about O to 10O ⁰ C, preferably +20 to +50 ⁰ C performed.

It is useful to use an alkaline compound, for example Add sodium hydroxide or potassium hydroxide or triethylamine or Ν, Ν-dimethyl-cyclohexylamine in a catalytic amount »

The compounds II used as starting materials are known from the literature and can be prepared from ketones of the formula IV and aldehydes of the formula V by customary processes. If the necessary amount of triazole is added, the active ingredients of the formula according to the invention are obtained directly in one step io These reactions are for example, alcohols such as methanol or ethanol or iso-propanol or in amides, for _o B _o dimethylformamide, at temperatures of about O ° to 100 ° C, preferably +20 to +50 ⁰ C and in the presence of a base, in Water dissolved catalyst, e.g. sodium hydroxide or potassium hydroxide carried out "

The compounds of the formula I according to the invention are colorless crystalline products, easily soluble in ethyl acetate, acetone, Ethanol, tetrahydrofuran, methylene chloride, chloroform, dimethyl sulfoxide, Dimethylformamide and N-methylpyrrolidone.

The new ß-azolyl ketones and their salts show a considerable broader fungicidal action and superior plant tolerance than the well-known 1- [l, 2,4-triazolyl- (l)] -2-C4 "-chlorophenoxy) -4,4-dimethyl-pentan-3-one"

The new active ingredients can also be used in the form of their salts, e.g. hydrochlorides, oxalates or nitrates.

709885/0452

-X- OoZ 32 114

The fungicidal agents according to the invention are of great interest Remedies for fungal diseases on various cultivated plants, ζ.Β «at

Ustilago scitaminea (sugar cane brandy)

Hemileia vastatrix (coffee rust)

Uromyces fabae or appendiculatus (bean rust) Puccinia species (grain rust)

Erysiphe graminis (cereal mildew)

Botrytis cinerea on vine, strawberries,
Uncinula necator,
Sphaerotheca fuliginea,
Erysiphe cichoracearum,
Podosphaera leucotricha.

In this context we understand crop plants in particular Wheat, rye, barley, oats, rice, corn, apple growing, cucumber, beans, coffee, sugar cane, grapevine, strawberries as well Ornamental plants in horticulture.

The active compounds according to the invention are systemically effective. The systemic effectiveness of these agents is special Interest in connection with the fight against internal plant diseases e.g. grain rust, powdery mildew.

The agents according to the invention can suppress and possess the growth of two or more of the fungi mentioned at the same time high plant tolerance. The application rates required to combat the phythopathogenic fungi are between 0.05 and 2 kg active ingredient / ha of cultivated area.

As examples of the active ingredients that can be used according to the invention, the following may be mentioned in detail:

1- Fl, 2,4-triazolyl- (1)] -1-pheny1-4,4-dimethyl-pentan-3-one l-ri, 2,4-triazolyl- [lJ [-l- (p-tolyl) -4, il-dimethylpentan-3-one

-5- 709885/0452

- Ϋ- OZ 32 114

1- II, 2,4-triazoly l-d ^ -1- (4'isopropyl-phenyl) -ll, l <-dimethyl-

pentan-3-one

1- [1,2,4-Triazolyl- (1)] - 1- (1'-naphthyD-U, 4-dimethyl-pentan-3-one i- [1,2,4-triazolyl- (1)] -1- (3'-thienyl) -4,4-dimethyl-pentan-3-one 1- [1,2,4-triazoly 1- (1)] -1- (2'-furyl) -4,4 -dimethyl-pentan-3-one 1- [1,2,4-triazolyl- (1) f -1- (4'-chlorophenyl) -butan-3-one 1- [1,2,4-triazolyl - (1)] -1- (4 '-chloro-phenyl) -4-methyl-pentan-3-one 1- [1,2, ¹ J-TrIaZoIyI- (I) I -1- (4' -chloro -phenyl) -5,5-dimethy 1-hexane

3-on

1- [1,2,4-triazolyl- (1)] -1- (4'-chlorophenyl) -4,4-dimethylpentane

3-on

1- [i, 2,4-triazolyl- (I)] -l- (4'-bromophenyl) -4,4-dimethylpentane

3-one! - h _y 2 , Ί-triazolyl- (1)] -1- (3'-chlorophenyl) -4,4-dimethylpentane

3-one 1- [l, 2, iJ-Triazoly 1- (1)] -1- (2 ', 4'-dichlorophenyl) -4,4-dimethy 1-

pentan-3-one l- [l, 2, iJ-Triazolyl- (l)] - l- (3 ', ¹ < ^l -dichlorophenyl) -4, i | -dimethylr

pentan-3-one l- [l, 2, i | -triazolyl- (l)] - l- (4'-trifluonnethyl-phenyl) -1, 'J-diinethyi-

pentan-3 ~ one 1- [l, 2,4-triazoly 1- (1)] -1- (4 '-nitro-pheny 1) -4,4-dimethy 1-pentane

3-one 1- [1,2,11-triazolyl- (I)] -l- (4'-methoxyphenyl) -4,4-dimethyl-

pentan-3-one 3- [l, 2,4-triazoly 1- (I)] -3- (4'-methoxyphenyl) -1- (2-norbonyl) -

propan-1-one j 3- [1,2,4-triazoly 1- (I)] - 3- (2 ^l -allyloxyphenyl) -1- (4'-chloro-phenyl ^

propan-1-one

3- [1,2,4-Triazoly 1- (I)] -3- (2 · -allyloxy-phenyI) -I- (2 ", 4 '-dichloropheny l) -propan-l-one

3- [1,2,4-Triazoly 1- (I)] -1-phenyl-3- (4'-chlorophenyl) propan-1-one 3- [1,2,4-Triazoly 1- (I)] -1,3-bis (4'-chloro-phenyl) -propan-1-one 3- [1,2,4-Triazoly 1- (I)] -1- (4'-chlorophenyl) -3- (p-tolyl) -propane-

1-one 3- [l, 2,4-triazolyl- (1) J -1- (2 ', 4'-dichlorophenyl) -3-pheny 1-propane

3- £ 1,2,4-Triazoly 1- (I)] -1- (4'-chlorophenyl) -3- (2 '^ "- dichloropheny 1) -propane-l = on_ 709885/0452

example 1

-, 6 - O.Z. 32

OV C0-CH _p -CH- (O) -Cl

Vy ₁ · ^HC i

24.8 g (0.1 mol) of 1-phenyl-3- (4'-chlorophenyl) -prop-2-en-l-one, 11 g of 1,2,4-triazole (0.15 mol) and 0 , 3 g of potassium hydroxide are dissolved in 200 ml of dimethylformamide and ^{stirred at ^ 5 °} C. for 10 hours. The solvent is then distilled off in vacuo, the residue is dissolved in 300 ml of ether and the organic solution is washed twice with 100 ml of water each time. The organic phase is then dried over sodium sulfate, filtered off and gassed with hydrogen chloride gas. The precipitate of 3- [1,2,4-triazolyl- (l)] -l-phenyl-3- (4'-chlorophenyU-propan-l-one hydrochloride is filtered off with suction and dried. Yield: 20 g of white crystals of melting point 156-158 ⁰ C (83Ϊ) next to 7.4 g of recovered l-phenyl-3- (4'-chloro-phenyl) -prop-2-en-l-one. Analogous listed in the following table Connections made.

-7-709885 / 0452

Tabel

Connection R No.

R ^ CO-CH.-CH-R ² ^ ι

JK

ί // ^Ν

LJ

R '

O. Z. 32 114

Melting point C.
Base hydrochloride

12th

(CH ₃ J ₃ C-

(CH,), C-

(CH ₃ J ₃ C

(CH ₃ J ₃ C

10

11 CH ₃ -

CH,

CH

(CH ₃ ) ₃ C

Cl

69-71

141-143 153-155

155-157

162-164 118-120 156-160

118-120 139-141

110-111 69-72

146-147

-8th-

709885/0452

Connection R No.

O.Z. 32 114

Melting point ⁰ C base hydrochloride

(CH ₃ O ₃ C-

(CH ₃ J ₃ C-

(CH ₃ J ₃ C-

Br- (O Cl-

112-1Ί5 154-156

158-I6O 166-168 164-167

(CH ₃ J ₃ C-

20 Ci- (O;

21 ci

^C 6 ^H 5 "

CH ₃ O- (O,

■ CH, 0- (Oy

0-CH ₂ -CH = CH ₂

-CH ₂ -CH = CH ₂

Cl- (O '

I58-I6I

78-82 156-158

94-95

156-158 115-117

Cl- (O '

H ₃ C- (O 81-82

-9-

709885/0452

Connection R 'No.

-r-

OZ 32 114 melting point ⁰ C base hydrochloride

Cl-

^ C ₁

I36-I39

I35-I38

= CH-CH ₂ -

49-50

IO5-IO7 145-1 ^ 8

CH ₂ = CH-CH ₂ -O Cl

162-165

The active compounds according to the invention can be used in the customary formulations such as solutions, emulsions, suspensions, powders, pastes and granulates. These are done in a well known manner produced, e.g. by mixing the active ingredient with solvents and / or carriers, optionally using Emulsifiers and dispersants, where in the case of the use of water as a diluent, other organic solvents are also used can be used as co-solvents. As auxiliary materials The following essentially come into question: Solvents such as aromatics (e.g. xylene, benzene), chlorinated aromatics (e.g. chlorobenzenes), Paraffins (e.g. petroleum fractions), alcohols (e.g. methanol, butanol), amines (e.g. ethanolamine, dimethylformamide) and water; Carriers, such as natural ground rock (e.g. kaolins, clays, talc, chalk) and synthetic ground rock (e.g. highly dispersed silica

-10-

70988 5/0452

- ys - ^ ο.ζ. 32 ii4

/ ίο

acid, silicates); Emulsifiers such as nonionic and anionic Emulsifiers (e.g. polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants such as lignin, sulfite waste liquors and methyl cellulose «

The formulations generally contain between 0.1 and 95 percent by weight Active ingredient, preferably between $ 0.5 and $ 90. The formulations or the ready-to-use preparations made from them, such as solutions, emulsions, suspensions, powders, Pastes or granules are used in a known manner, for example by spraying, atomizing, dusting, scattering or pouring.

The agents according to the invention can be used in these forms also be present together with other active ingredients, e.g. Herbicides, insecticides, growth regulators and fungicides or also with Fertilizers are mixed. Fungicides which can be combined with the compounds according to the invention are for example Dithiocarbamates and their derivatives, such as

Ferric dimethyl dithiocarbamate,

Zinc dimethyldithiocarbamate,

Manganese ethylene bisdithiocarbamate,

Manganese-zinc-ethylenediamine-bis-dithiocarbamate, Zinc ethylene bisdithiocarbamate,

Tetramethylthiuram disulfide,

Ammonia complex of zinc (N, N-ethylene-bis-dithiocarbamate) and N, N'-polyethylene-bis (thiocarbamoy1) -disulfide zinc (N, N ^l -propylene-bis-dithiocarbamate), ammonia complex of tin (N, N'-propylene-bis-dithiocarbamate) and NjN'-polypropylene-bis-cthiocarbamoyl) disulfide

Nitrophenol derivatives, such as

Dinitro (1-methylheptyl) phenyl crotonate, 2-sec-butyl-iJ, 6-dinitropheny 1-3,3-dimethylacrylate, 2-sec-butyl-4,6-dinitrophenyl iospropyl carbonate;

heterocyclic structures such as
N-trichloromethylthio-tetrahydrophthalimide,

-11-

709885/0452

- yi -,. ο.ζ. 32 ιΐ4

N-trichloromethylthio-phthalimide,

2-heptadecyl-2-imidazoline acetate,

2,4-dichloro-6- (o-chloroanilino) -s_-triazine, 0, O-diethy1-phthalimidophosphonothioate, 5-Amino-1- bis- (dimethylamine)) - phosphinyl ^ - 5-ethoxy-3-trichloromethyl-1,2,4-thiadiazole 2,3-dicyano-1,4-dithiaanthraquinone,

2-thio-1,3-dithio- (4,5-b) -quinoxaline,

l- (Butylcarbamoyl) -2-benzimidazole-carbamic acid methyl ester, 2-methoxycarbonylamino-benzimidazole,

2-rhodanemethylthio-benzothiazole,

4- (2-chlorophenylhydrazono) -3-niethyl-5-isoxazolone, Pyridine-2-thiol-1-oxide,

8-Hydroxyquinoline or its copper salt, 2,3-dihydro-5-carboxanilido-6-methyl-1, ^ -oxathiin- ¹ !, 4-dioxide, 2,3-dihydro-5-carboxanilido-6-methyl-1 , ⁱ l-oxathiine, 2- puryl- (2) -benzimidazole,

Piperazine-1,4-diyl-bis- (2,2,2-trichloro-ethyl) -formamide, 2- [thiazolyl- (4) -benzimidazole,

5-butyl-2-dimethylamino- ⁱ -hydroxy-6-methyl-pyrimidine, bis- (p-chlorophenyl) -3-pyridinemethar.ol,

1,2-bis- (3-ethoxycarbony1-2-thioureido) -benzene, 1,2-bis- (3-methoxycarbony1-2-fchioureido) -benzene,

and various fungicides, such as
Dodecylguanidine acetate,

3- [2- (3,5-Dimethy1-2-oxycyclohexyl) -2-hydroxyethylj-glutarimide, Hexachlorobenzene,

N-dichlorofluoromethylthio-N ', N ^t -dimethyl-N-phenyl-sulfuric acid-

diamid,

2,5-dimethyl-furan-3-carboxylic acid anilide, 2,5-dimethyl-furan-3-carboxylic acid-cyclohexylamide, 2-methyl-benzoic acid-anilide,
2-iodo-benzoic acid anilide,
1- (3,4-dichloroanilino) -l-formylamino-2,2,2-trichloroethane,

709885 / 04S2

- 1 * - O.Z. 52 114

2,6-Dimethyl-N-tridecyl-morpholine or its salts, ^ DOhQ I I Sjö-dimethyl-N-cyclodecyl-morpholine or its salts, 2,3-dichloro-l, Ί-naphthoquinone,

1, ¹ I-DiChIOr-2,5-dimethoxybenzene,

p_-dimethylaminobenzene diazo sodium sulfonate, l-chloro-2-nitro-propane,

Polychloronitrobenzenes, such as pentachloronitrobenzene, methyl isocyanate, fungicidal antibiotics such as griseofulvin or kausgamycin, tetrafluorodichloroacetone, 1-phenylthiosemicarbazide, Bordeaux mixture, compounds containing nickel and sulfur.

For combating powdery mildew and rust diseases on cereals was an effect-increasing effect (synergism) when using 1- [1,2,4-triazolyl- (l) J -l- (4'-chlorophenyD - ^ - dimethylpentan-3-one or 1- [l, 2,4-triazolyl- (l)] -l- (2 ', V-dichlorophenyl) -4,4-dimethylpentan-3-one, either as bases or in the form of their salts in a mixture with N-tridecyl-2,6-dimethylmorpholine and its Salting achieved. The increase in effectiveness is particularly clear the mixing ratios 1: 2 to 1: 4 parts by weight to be observed.

The following examples explain the fungicidal action of the new active ingredients.

Example 28 Barley powdery mildew

Leaves of barley seedlings grown in pots are sprayed with aqueous emulsions of 8055 active ingredient and 2055 emulsifier and, after the spray coating has dried on, dusted with oidia (spores) of barley powdery mildew (Erysiphe graminis var. Hordei). The test plants are then in the greenhouse at temperatures between 20 and 22 ⁰ C and 75 to 80? relative humidity. The extent of powdery mildew development is determined after 10 days.

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709885 / 0A62

. ο.ζ. 32

0 no infestation, graded up to 5 total infestation 263451

Active ingredient Infestation of the leaves after fuel

Zung with ... J & iger Acts off the broth

0.1 0.05 0.025 0.012

3 0 0 0 0

9 0 0 0 0

lh 0 0 0 0

15 0 0 0 0

known (DT-OS 23 35 020)

Control (untreated) 5

Example 29 Wheat powdery mildew

Leaves of potted wheat seedlings of the variety "Anniversaries" are made with aqueous emulsions from 80? (Weight percent) Active ingredient and 20? Emulsifier sprayed and after the spray coating has dried on with oidia (spores) of wheat powdery mildew (Erysiphe graminis var. tritici) pollinated. The test plants are then in a greenhouse at temperatures between 20 and 22 ° C and 75 to 80 pounds relative humidity. To The extent of powdery mildew development is determined after 10 days.

709885/0452

- ΛΑ - OZ 32 114

Λ *

0 no infestation, graded up to 5 total infestation 263 451 1

Active ingredient Infestation of the leaves after fuel

tongues with ...?

0.05 0.025 0.012

9
10 13 14 15

0 0 0 0 0 0 0 0 0 0 0 0 0 0 0

known (DT-OS 23 35 020)

Control (untreated) 5

Example 30 Cucumber mildew

Leaves of cucumber seedlings grown in pots are added aqueous emulsions from 80? Active ingredient and 20? Sprayed emulsifier and, after the spray coating has dried on, with oidia (Spores) of cucumber powdery mildew (Erysiphe cichoriacearum) pollinated. The test plants are then placed in a greenhouse at temperatures between 20 and 22 ° C and 75 to 80? relative humidity. After 10 days the extent of Powdery mildew development determined.

-15-

709885/0452

Jß ° · ^ζ · 22

O no infestation, graded up to 5 total infestation

Active ingredient Infestation of the leaves after spraying

with ... £ iger active ingredient broth

7 O

8 O ⁺⁾

Control (untreated) 5

⁺ ^ slight leaf damage

Example 51

90 parts by weight of compound 9 are mixed with 10 parts by weight of N-methyl- <6-pyrrolidone and a solution is obtained which is suitable for
Application in the form of the smallest drops is suitable.

Example 52

20 parts by weight of compound 2 are dissolved in a mixture consisting of 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 mol of ethylene oxide with 1 mol of oleic acid-N-monoethanolamide, 5 parts by weight of the calcium salt of dodecylbenZOls ^ fonsäure and 5 parts by weight of the adduct of 40 Mole
Ethylene oxide consists of 1 mole of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives it
an aqueous dispersion containing 0.02 percent by weight of the active ingredient
contains.

Example 55

20 parts by weight of compound 5 are dissolved in a mixture those from 40 parts by weight of cyclohexanone, 50 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 moles of ethylene oxide with 1 mole of isooctylphenol and 10 parts by weight of the adduct of 40 moles of ethylene oxide to 1 mole of castor oil. By

-16- 709885/0452

- d / - O.Z. 32 114

Pour and finely distribute the solution in 100,000 parts by weight Water gives an aqueous dispersion which contains 0.02 percent by weight of the active ingredient.

Example 3 ¹ *

20 parts by weight of compound 4 are dissolved in a mixture which consists of 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction of boiling point 210 to 28O ⁰ C and 10 parts by weight of the adduct of 40 mol of ethylene oxide with 1 mole of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which contains 0.02 percent by weight of the active ingredient.

Example 35

20 parts by weight of the active ingredient 5 with 3 parts by weight of the Sodium salt of diisobutylnaphthalene sulfonic acid, 17 parts by weight of the sodium salt of a lignin sulfonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel are mixed well and ground in a hammer mill. By fine distribution the mixture in 20,000 parts by weight of water gives a spray mixture which contains 0.1 percent by weight of the active ingredient.

Example 36

3 parts by weight of compound 6 are intimately mixed with 97 parts by weight of finely divided kaolin. This way you get a Dust containing 3 percent by weight of the active ingredient.

Example 37

30 parts by weight of compound 7 are mixed with a mixture of 92 parts by weight of powdered silica gel and 8 parts by weight Paraffin oil, which has been sprayed onto the surface of this silica gel, is intimately mixed. This is how you get a Preparation of the active ingredient with good adhesion.

-17- 709885/0452

Example 38

Yi - OZ 32 114

20 263A511

40 parts by weight of the active ingredient 9 are mixed with 10 parts of the sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts Silica gel and 48 parts of water are intimately mixed. A stable aqueous dispersion is obtained. Dilution with 100,000 parts by weight of water gives an aqueous dispersion that is 0.04 percent by weight Contains active ingredient.

Example 39

20 parts of the active ingredient 8 are mixed with 2 parts of the calcium salt of dodecylbenzsulfonic acid-urea-formaldehyde condensate and 68 Parts of the sodium salt of a phenol-sulfonic acid-urea-formaldehyde condensate and 68 parts of a paraffinic mineral oil intimately mixed. A stable oily dispersion is obtained.

-18- 709885/0452

Claims (7)

P a t ο α t. α ■■ is ρ r ü * c h e 2v34bl I 1. ß-Azoly lketorie of the formula K ¹ -CO-CIU-CII-z
^d I in the R alkyl with up to ο carbon atoms, cycloalkyl and optionally ρ
substituted aryl, R is furanyl, thiophenyl, naphthyl or phenyl, the phenyl radical being substituted by halogen, alkyl, alkoxy, alkenyloxy, nitro, trifluorinethyl 1 2
kenn and R and Ii do not mean phenyl at the same time, like their salts. 2. Vei ^ drive for the production of ß-azolyl ketones and their ijalze according to claim 1, dad u rch characterized in that one a) Od, β-unsaturated ketones of the formula R ^ CO-CH = CH-R ² in which 1 2
R and R have the meaning given above, reacts with 1,2,4-trlazole, if appropriate in the presence of a basic catalyst and if appropriate in the presence of a diluent, or b) ß-haloketones of the formula R ¹ -C0-CH _o -CH-R ²
X in which 1 2
R and R have the meanings given above and X is halogen, or is reacted with 1,2,4-triazole, if appropriate in the presence of an acid binder and if appropriate in the presence of a diluent 7 0 ^ AH; b / Π U B 2
ORIGINAL INSPECTED - yf - " ο.ζ. 32 R ¹ ^ -CO-CH and an aldehyde of the formula
OCH-R ² in which 1 2
R and R are as defined above, are reacted with 1,2,4-triazole, if appropriate in the presence of a basic catalyst and if appropriate in the presence of a diluent, and the compounds thus obtained are, if appropriate, reacting with an acid. 3. Use of a ß-azolyl ketone according to claim 1 for combating of phytopathogenic fungi. ¹ J. Fungicide containing a β-azolyl ketone according to Claim 1. 5. Compound of formula CH _x -C-CO-CH_-CH- <Ö) -C1
CH / N _x ^ ri N N 6. Compound of Formula
CH CH ₃ -C- 85/0451 -? ό - OZ 32 114 7. Compound of Formula CH ₃ -C-CO-CH ₂ -CH- (O) -Cl ^c «3 BASF Aktiengesellschaft,