CS208791B2 - Fungicide means and method of making the active substances - Google Patents

Abstract

Die Erfindung betrifft neue substituierte N-Propargyl-aniline, mehrere Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide.

Die neuen Verbindungen der Formel in welcher R' bis R⁶ und die in der Beschreibung angegebene Bedeutung besitzen, können zum Beispiel dann erhalten werden, wenn man N-Propargyl-aniline mit Säurechloriden oder -bromiden bzw. -anhydriden in Gegenwart eines Verdünnungsmittels und gegebenenfalls in Gegenwart eines Säurebindemittels umsetzt. Daneben gibt es noch andere Verfahren.

Als Pflanzenschutzmittel können die erfindungsgemäßen Wirkstoffe mit besonders gutem Erfolg zur Bekämpfung von Oomyceten, z. B. gegen Phytophthora infestans eingesetzt werden.

Description

The invention relates to novel substituted N-propargylanilines, to a process for their preparation and to their use as fungicides.

It is already known that haloacetanilides, such as alkyl esters of N-chloroacetyl-N- (2,6-dimethylphenyijalanine or glycine), can be used with good results in combating fungal diseases of plants (cf. U.S. Pat. No. 2,350,944 or U.S. Pat. However, the effect of these substances, in particular when applied at lower levels and concentrations, and in particular also in combating Phytophthora species, is not always entirely satisfactory.

New substituted N-propargylanilines of the formula I have now been found

in which

R 1 and R ² independently of one another are alkyl having 1 to 4 carbon atoms,

R ⁵ represents a hydrogen atom or a methyl group and

R ⁶ is dichloromethyl, furyl, methoxymethyl, 1-imidazolylmethyl, 1,2,4-triazol-1-ylmethyl or 5-methyloxazol-3-yl.

The above compounds have strong fungicidal properties.

The substituted N-propargylanilines of the above general formula (I) according to the invention are obtained by reacting the N-propargylanilines of the general formula II

R * H (II) in which

R1, ^R2 and ^R5 are as defined above,

N

С-СНгHlť

II are reacted with chlorides, bromides or acid anhydrides corresponding to the general formulas IIIa or IIb,

R6 — C — Cl (Br) ·

O (IIIa), (R 6 -C 2) 2 O

O (The Kiss) in which

R ⁶ is as defined above, in the presence of a diluent and optionally in the presence of an acid binding agent.

Alternatively, the compounds of the invention can also be prepared by treating anilides of formula IV

(IV) wherein

R, R ² and R® have the abovementioned meaning, are reacted with propargyl halides of the formula V

Hal - CH - C - C - R R (V), (VI) in which

R ¹ , R ² and R ⁵ are as defined above and

Hal 'represents -chlorine, bromine or iodine, reacted with compounds of formula VII

Β — X, VII), in which

X is methoxy, 1-imidazolyl or 1,2,4-triazol-1-yl, and

B represents a hydrogen atom or an alkali metal, optionally in the presence of a diluent and optionally in the presence of an acid binding agent [variant c)].

The novel substituted N-propargylanilines of the invention have potent fungicidal properties. Surprisingly, the compounds according to the invention exhibit a considerably higher effect than the known alkyl esters of N-chloroacetyl-N- (4-chloro-1-alanine or glycine).

In addition to the compounds of the Examples, the following compounds of Formula I are mentioned as specific examples:

CH, -CeC-R 5

N \: - R * II (D in which

R 5 is as defined above and

Hal represents chlorine or bromine, in the presence of an acid-binding agent and optionally in the presence of an organic diluent or in an aqueous-organic biphasic system in the presence of a phase transfer catalyst [variant b)], or

I, haloigenation-tanilides of formula VI

R1 R2 208791 R5 Κ ^ϋ CHs 6-CH 2 H AND? CHs 6-CH 2 H - CH2OCHs СНз 6-CH 2 H -CH- ^nQ \ = N CHs 6-CH 2 H - ^ch ž'Q CHs 6-CH 2 CHs CHs 6-CH 2 CHs - CH2OCHs CHs 6-CH 2 CHs 1 CHs 6-CH 2 CHs / = ^ CHs 6-CH 2 CHs —CHC12 CHs 6-C2H5 H CHs 6-C2H5 H - CH2OCHs CHs 6-C2H5 H CHs 6-C2H5 H —CHCl2 CHs 6-C2H5 CHs JQ CHs 6-C2H5 CHs - CH2OCHs A / ____ CHs 6-C2H5 CHs Vz / y CHs 6-C2H5 CHs —CHC12 C2H5 6-C2H5 H zu C2H5 6-C2H5 H - CH2OCHs C2H5 6-C2H5 H ^CH r ^N U \ = N C2H5 6-C2H5 H —CHCl2 C2H5 6-C2H5 CHs C2H5 6-C2H5 CHs —CH2OCHs C2H5 6-C2H5 CHs / Ί - ^CH from K \

If, for example, α-2-furancarboxylic acid chloride is used as the starting material, the following reaction scheme may be used to describe the course of the reaction according to the invention:

CWj

Z - 1 ⁺ ct-co AqJI CH ₃ CH ₃ + 6 and ze / - <CH3C = CH -HCl ' CH ₃ 0

If, for example, 2 are used as starting materials, (4-methyl-1-methyl-2-methyl-2-methyl-2-methyl-2-methyl-2-methyl-2-yl) -bromide and bromide , the reaction sequence according to variant bj can be described by the following reaction scheme:

+ Br-CH ^C CCH + te

-HBr

CH _y

H n '____, \ _c 10 _CH 5V

When used as starting materials, for example

2,6-dimethyl-N-propyl chloroacetanone and imidazole, the reaction of the process according to variant c) can be described by the following reaction scheme:

The starting N-propargylanilines of the general formula II are known in some cases (see U.S. Patent Nos. 3,535,377 and 4,001,325) or can be obtained in a known manner, for example by reacting the corresponding anilines with propargyl halides of the aforementioned general formula (V) or with the corresponding propargylsulfonates, for example -methylates or -tosylates, in the presence of an acid binding agent such as sodium carbonate or potassium carbonate, and optionally in the presence of an inert organic solvent such as ethanol at a temperature between 20 and 150 ° C; preferably an excess of aniline may also be used.

The following compounds are exemplified as starting materials of formula II:

R1

R2

R ⁵

CH3 6-CH3 H C2H5 6-C2H5 H C2F2O4 6-CH3 H CH3 3-CH3 H CH3 5-CH3 H CH3 6-CH5 CH3 C2H5 6-C2H5 CH3 C2H5 6-CH3 CH3

The chlorides, bromides or acid anhydrides used as further starting materials in the process according to the invention are generally defined by the above formulas IIIa and IIIb.

The chlorides, bromides or anhydrides corresponding to the formulas IIIa and IIIb are generally known compounds in organic chemistry.

The anilides of the formula IV used as starting materials in the process of variant b] can be obtained in a manner known per se by reacting the corresponding anilines with the chlorides, bromides or anhydrides of the acids of the formulas IIIa and IIIb. in the presence of an inert organic solvent such as toluene or methylene chloride, optionally in the presence of an acid binding agent such as potassium carbonate or triethylamine, or in the presence of a catalyst such as dimethylformamide at a temperature between mezi and 100 ° C (see also examples).

The following compounds are exemplified as starting materials of formula IV:

R ⁶

CHs 6-CH3 xU C2H5 6-CH3 C2H5 6-C2H5 CH3 6-CH3 —CH2-O — CH3 C2H5 6-CH3 —CH2 —O — CH3 C2H5 6-C2H5 —CH2 —O — CH3 / = 7 CH3 6-CH3

R1 R2 R ⁶ / = 1 C2H5 6-CH3 C2H5 6-C2H5 AT CH3 6-CH3 C2II5 6-CH3 -снХП ² in,!. C2H5 6-C2H5 \ —Л / CH3 6-CH3 - Oh —CHC12 C2H5 6-CH3 —CHCI 2 C2H5 6-C2H5 —CHC12 CH3 3-CH3 —CHC12

The propargyl halides of the general formula V used as further starting materials in the process of variant b) are generally known compounds in organic chemistry.

The haloacetanilides of the general formula (VI) used as starting materials in the process of variant c) are partially known (cf. U.S. Pat. No. 4,001,325). Until now unknown compounds of this type can be prepared as described in this U.S. Pat. of the invention by reacting the N-propargylanilines of the formula II with halides of haloacetic acids.

The compounds used as further starting materials in the work of variant c] are generally defined by the above formula VII.

Compounds of formula VII are generally known in organic chemistry.

Suitable diluents for use in the process according to the invention are preferably inert organic solvents. to whom. preferably include ketones such as diethyl ketone, and especially acetone and rm (methyl) ketones, nitriles such as propionitrile - and especially acetonitrile, ethers such as tetrahydrofuran or dioxane, aliphatic and aromatic hydrocarbons such as propetrol ether, benzene, toluene or xylene, halogenated hydrocarbons , such as methylene chloride, carbon tetrachloride, chloroform or chlorobenzene, and esters such as ethyl acetate.

The reaction according to the invention can optionally be carried out in the presence of acid-binding agents (hydrogen halide acceptors). All conventional acid-binding agents, preferably organic bases, such as tertiary amines, for example triethylamine or pyridine, and inorganic bases such as alkali metal hydroxides and alkali metal carbonates, and optionally a catalyst such as dimethylformamide may be used.

The reaction temperatures of the process according to the invention can be varied within a wide range. In general, the reaction is carried out at a temperature between 0 and 120 ° C, preferably between 20 and 100 ° C.

The starting materials used in the process according to the invention are preferably used in a motor. quantity. Insulation. The compounds of formula I are carried out in the usual manner.

As a diluent for work within the meaning of the variant

b) suitable are all inert organic solvents, which preferably include ethers such as diethyl ether, dioxane or tetrahydrofuran, aromatic hydrocarbons such as benzene, toluene or xylene, halogenated hydrocarbons such as methylene chloride, carbon tetrachloride, chloroform or chlorobenzene, esters such as ethyl acetate ketones, such as methylisoibutyl ketone, nitriles, such as acetonitrile, as well as dimethylformamide or dimethylsulfoxide.

The reaction of variant b) is carried out in the presence of an acid binding agent. Like this. All conventional acid acceptors, which preferably include inorganic bases such as alkali metal hydroxides and alkali metal carbonates, can be used.

The reaction temperatures for the operation of variant b] can be varied within a wide range. In general, the reaction is carried out at a temperature of between -70 and 4-100 ° C, preferably between -20 and -20 °.

+ 80 ° C.

In the process according to variant b) of the process according to the invention, preferably 1 to 1.5 moles of propargyl halide of the formula V are used per 1 mol of anilide of the formula IV.

According to a preferred embodiment, the reaction of variant b) is carried out in a two-phase system, such as aqueous sodium or potassium hydroxide solution - toluene or methylene chloride, with the addition of

0.1 to 1 mol of phase transfer catalyst, such as ammonium or phosphonium compounds, for example benzyldodecyldimethylammonium chloride or triethylbenzylammonium chloride (see also examples).

Suitable diluents for work according to variant c) are preferably inert organic solvents, which preferably include those already mentioned in the description of the process according to the invention.

Optionally, the reaction of variant c) may be carried out in the presence of an acid binding agent. In this case, all customary inorganic or organic acid acceptors, such as alkali metal carbonates, such as sodium carbonate, potassium carbonate or sodium bicarbonate, or lower tertiary alkylamines, cycloalkylamines or aralkylamines, such as triethylamine or dimethylbenzylamine, or further pyridine and diazabicyclooctane can be used. . Preferably, an excess of the starting azole is used for this purpose.

The reaction temperatures for operation according to variant c) can be varied within a wide range. In general, the reaction is carried out at a temperature of between approximately 20 and 150 ° C, preferably at a temperature of 60 to 120 ° C. In the presence of a solvent, the reaction is expediently carried out under boiling.

In the process according to variant c), preferably 1 to 2 mol of the compound of the formula (VII) and optionally 1 to 2 mol of the acid-binding agent are used per mole of the compound of the formula VI. The isolation of the compounds of formula (I) is carried out in a conventional manner.

The active compounds according to the invention show a strong microbicidal action and can be used in practice for the collection of undesirable microorganisms. These active compounds are suitable for use as plant protection agents.

Fungicidal agents are used in plant protection to combat fungi of the classes Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes.

Since the plants of the present invention are well tolerated at the concentrations required to combat plant diseases, they can be used to treat aboveground parts of plants, seedlings and seeds, as well as soil.

As plant protection agents, the active compounds according to the invention can be used with particularly good results in combating fungi of the Oomycetes class, for example Phytophthora infestans (mold fungus), which causes mold and dizziness of tomatoes and potatoes. It is particularly advantageous that the active compounds according to the invention exhibit not only a protective but also a curative effect. In addition, these substances have a systemic activity which makes it possible to protect the plants against fungal infestations by feeding the active substance to the above-ground parts of the plant via soil and the root system or through seeds.

The active substances can be converted into the customary formulations such as emulsion solutions, wettable powders, suspensions, powders, dusts, foams, pastes, soluble powders, granules, aerosols, suspension and emulsion concentrates, seed dressing powders, natural and synthetic substances impregnated with active substances, small particles coated with polymeric substances and coating materials for seeds, further with means of inflammable additives such as smoke cartridges, smoke boxes, smoke spirals and the like, as well as formulations of active substance concentrates for fog dispersion cold or hot.

These compositions are prepared in a known manner, for example by mixing the active ingredient with fillers, i.e. liquid solvents, with liquefied gases under pressure and / or solid carriers, optionally using surfactants, i.e. emulsifiers and / or dispersants and / or foaming agents. If water is used as a filler, it is also possible to use, for example, organic solvents as co-solvents. Basically suitable liquid solvents are: aromatics such as xylene, toluene or alkyl naphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, alcohols such as butanol or glycol, as well as their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide, and dimethylsulfoxide, and water. By liquefied gaseous fillers or carriers is meant those liquids which are gaseous at normal temperature and pressure, for example aerosol propellants such as halogenated hydrocarbons, as well as butane, propane, nitrogen and carbon dioxide. Suitable solid carriers are: natural stone meal, such as kaolins, alumina, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and synthetic stone meal, such as highly disperse silica, alumina and silicates. Suitable solid carriers for the preparation of granulates are crushed and fractionated natural stone materials such as limestone, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, coconut shells , corn sticks and tobacco stalks. Suitable emulsifiers and / or foaming agents are non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, fatty alcohol polyoxyethylene ethers, e.g.

The compositions of the invention may comprise adhesives such as carboxymethylcellulose 207979 for natural and synthetic powdered, granular or latex polymers such as gum arabic, polyvinyl alcohol and polyvinyl acetate.

In addition, these compositions may contain coloring agents such as inorganic pigments, for example iron oxide, titanium dioxide and ferrocyanide blue, and organic dyes such as alizarin dyes and metallic azo-phthalocyanine dyes, as well as trace elements such as iron, manganese salts, boron, copper, cobalt, molybdenum and zinc.

The concentrates generally contain between 0.1 and 95% by weight, preferably between 0.5 and 90% by weight, of active ingredient.

The active compounds according to the invention can be present in the formulations in admixture with other active compounds, such as fungicides, insecticides, acaricides, herbicides, anti-ozone preservatives, growth agents, plant nutrients and soil-improving agents.

The active compounds according to the invention can be applied as such, in the form of concentrates or from further dilution forms prepared therefrom, such as ready-to-use solutions, emulsions, suspensions, powders, pastes and granules. The application is carried out in a conventional manner, for example by watering, dipping, spraying, fogging, evaporation, injection, anointing, dusting, dusting, dry, wet, wet or suspension or incrustation.

When the active ingredients are used as foliar fungicides, their concentrations in the applied compositions can vary within wide limits. These concentrations generally lie between 1 and 0.0001 wt. %, preferably between 0.5 and 0.001 wt. %.

In the treatment of seed, it is generally necessary to use from 0.001 to 50 g, preferably 0.01 to 10 g, of active compound per kilogram of seed.

Depending on the site of action, concentrations of active compound of from 0.00001 to 0.1 wt. %, preferably from 0.0001 to 0.02 wt. %.

Example A

Potato Mold Test (Phytophthora) - Protective Effect / Tomato Solvent:

4.7 parts by weight of acetone emulsifier:

0.3 parts by weight of alkylaryl polyglycol ether water:

parts by weight

The amount of active ingredient required to achieve the desired concentration of active ingredient in the spray liquid is mixed with the indicated amount of solvent and concentrate. is diluted with the indicated amount of water containing said additives.

Young tomato plants in the 2 to 4 leaf stage are sprayed with the spray liquid until dew condensation occurs. The plants are kept for 24 hours at 20 ° C and 70% relative humidity in a greenhouse. Then, tomato plants are inoculated with an aqueous suspension of Phytophthora infestans. The plants are transferred to a humid chamber where they are maintained at 100% relative humidity and at a temperature of 18-20 ° C.

After 5 days, the infestation of the tomato plants is determined and the infestation is calculated in%. 0% (means no infestation, 100% - means complete - infestation - of plants).

The active substances, the active substance concentrations and the results obtained are shown in the following table:

Table A test - for - - Potato blight (Phytophthora) —protective / tomato active ingredient infestation in% at active substance concentration 0.0005%

[known)

^ CHiC-O-Cl ·

II z

O (known) active substance attack in% at active substance concentration 0.0005%

CH 2 C = CH / *

(1)

Example B

Systemic Effect Test on Potato Mold (Phytophthora) / Tomato Solvent:

4.7 parts by weight of acetone dispersant:

0.3 parts by weight of alkyl aryl glycol ether water:

parts by weight

The amount of active ingredient required to achieve the desired active ingredient concentration in the dressing is mixed with the stated amount of solvent and the concentrate is diluted with the specified amount of water containing the above ingredients.

Tomato plants planted in standard soil are poured at the 2 to 4 leaf stage with 10 ml of watering at the concentration of active substance below, based on 100 cm3 of soil.

The plants so treated are inoculated with an aqueous suspension of spores of the late blight (Phytophthora infestans) and then transferred to a humid chamber with 100% air humidity and a temperature of 18 to 20 ° C. After 5 days, infestation of the tomato plants is determined and converted to infestation in%. 0% means no infestation, 103% means complete infestation of plants.

The active substances, active substance concentrations and results obtained are summarized in the following table:

Table V systine effect test on potato (Phytophthora) / tomato active substance attack in% at active substance concentration 100 ppm

сн _ъ о

CH 2 C-O-C ₂ H _s -c-ch ₂ ci

II ² o

(2)

(51

Preparation of the starting material

The preparation of the active compounds according to the invention is illustrated by the following non-limiting examples.

Example 1

15.9 g [0.1 mol] of 2,6-dimethyl-N-propargylaniline and 8 g (0.1 mol) of pyridine are heated to boiling in 100 ml of tetrahydrofuran and 13 g (0.1 mol) are carefully added to the mixture. of 2-furancarboxylic acid chloride. The reaction mixture was stirred at reflux for 15 minutes, after which time the solvent was distilled off in vacuo. The residue is taken up in methylene chloride, the solution is washed with water, the organic phase is separated and, after drying over sodium sulphate, evaporated. The residue crystallizes after trituration with petroleum ether. It is obtained

22.5 g (89% of theory) of 2,6-dimethyl-N- [2-furoyl) -N-propargyianiline, m.p. 109-112 ^° C.

Preparation of the starting material

CH 2 C = CH n 'p d, 6-dimethyl-bopaopargylaniline is obtained by reaction of 2,6-dimethylaniline and propargyl bromide using a literature procedure (see U.S. Pat. No. 4,001,325).

(variant b)

21.5 g (0.1 mol) 2,6-dimethyl-N- (2-furoyl) aniline and 0.5 g triethylbenzylammonium chloride are dissolved in a two-phase mixture consisting of 50 ml · 50% sodium hydroxide solution ·· and 250 ml toluene, and dropwise added dropwise with vigorous stirring at 20-35 ° C

13.1 g (0.11 mol) of propargyl bromide. The reaction mixture is stirred at 20 DEG C. for 2 hours, then the organic phase is separated, washed several times with water, dried over sodium sulphate and the solvent is distilled off in vacuo. The residue crystallizes after trituration with petroleum ether. There was obtained 21 g (83% of theory) of 2,6-dimethyl-N- (2-furoyl) -O-fluorosulfonate, m.p. 110-112 ° C.

To a solution of 55.7 g (0.46 mole) of 2,6-cdimethylaniline and 46.5 g (0.46 mole) of triethylamine in 500 ml of methylene cmole was added dropwise with stirring at 0 to 10 ° C. 60 g (0.46 mol) of 2-furancarboxylic acid chloride. The reaction mixture was stirred at 20 ° C for 2 hours and the precipitated salt was filtered off with suction. The filtrate was washed several times with water, dried over sodium sulfate and the solvent was distilled off in vacuo. After recrystallization of the residue from a mixture of cyclohexane and toluene, 78.4 g (79% of theory) of 2,6-dimethyl-4-N-N- (2-furoyl) aniline is obtained, m.p. 119-122 ° C.

Example 2

C-CH ² OC ^H 3 (variant b) g (0.155 mol) 2,6-dimethyl-N-methoxyacetaniline and 0.3 g triethylbenzylammonium chloride are dissolved in a two-phase mixture consisting of 100 ml 50% sodium hydroxide solution and 250 ml toluene and 19 g (0.016 mol) of propargyl bromide are added with vigorous stirring. The reaction mixture is stirred for 4 hours, then the toluene phase is separated, washed several times with water, dried over sodium sulphate and the solvent is distilled off under a water pump vacuum. Distillation of the residue in a high vacuum yielded 26.5 g (74% of theory).

2,6-Dimethyl-N-hethoxeacetyl-N-proparine, b.p. 140 DEG C./67 DEG C., m.p. 49 DEG-51 DEG.

Preparation of the starting material

To a solution of 61 g (0.5 mol) 2,6-dimethylaniline with 50.5 g (0.5 mol) triethylamine in

250 ml of toluene are added dropwise, while cooling and cooling, at 5 DEG to 15 DEG C., 55 g (0.5 mol) of methoxyacetyl chloride are added dropwise. The reaction mixture was stirred at 20 ° C for 2 hours, then filtered, evaporated and the residue was taken up in water. The solution was extracted with methylene chloride, the extract was dried over sodium sulfate and the solvent was distilled off. By distillation of the residue in a high vacuum, 55 g (57% of theory) were obtained.

2,6-dimethyl-thiocyanate having a boiling point of 122 to 132 ° C / 13 Pa and a melting point of 61 to 63 ° C.

Example 3

/ CH ~ C = CH сл ° (variant c)

A molten mixture of 13.2 g (0.05 mol) of 2,6-diethyl-N, N-carboxylic acid acetic acid and 13.6 g (0.2 mol) of imidazole was stirred at 120 ° C for 30 minutes and then added to water.

The precipitate is filtered off with suction and washed thoroughly with water. After recrystallization from a mixture of diisopropyl ether and ethyl acetate, 10 g (63% of theory) of 2,6-dimethyl-N- (1-imidazolyl-1-acetyl-N-propargylaniline, m.p. 129-131 ° C) are obtained.

Preparation of the starting material

pšCH

CH * Cl ^u

The above starting material is prepared as described in the literature (U.S. Pat. No. 4,001,325) by:

The 2,6-dicthylaniline is reacted with propargyl bromide in the presence of potassium carbonate and the resulting 2,6-diethylipropargylaniline is treated with chloroacetic acid chloride or anhydride.

The following compound of formula I is obtained in an analogous manner:

example R1 R ² R ⁵ R ⁶ melting point number (° C) 4 CH3 6-C2H5 H / = N 129 to 131 5 CHs 6-CH3 CH3 JU 110 to 112 6 CH3 6-CH3 H / = 7 - ^Cr 120 to 121 7 CH3 6-CH3 H / == N 137 to 140 8 CH3 6-C2H5 H ZQ 88 9 CHs 6-CH3 CH3 —CH2 —O — CH3 n _D ²⁰ = 1.5362 boiling point 125 ° C / 13 Pa 10 C2H5 6-C2H5 H —CH2 —O — CH5 74 11 CH3 6-CH 2 H —CHC12 114 to 115

R ² R ⁵ R ^B Example R ¹ Number Melting point (° C)

12 СНз 6-СНз Η 13 СНз 6-СНз Η 14 C2H5 6-С2Н5 Η

CH 2 OCH 3 to 99 oil to 97

Claims (2)

OBJECT OF THE INVENTION A fungicidal composition, characterized in that it contains at least one substituted N-propargylaniline of the formula I (I) in which: R ¹ and R ² independently of one another are alkyl having 1 to 4 carbon atoms, R ⁵ represents a hydrogen atom or a methyl group and R ⁶ is dichloromethyl, furyl, methoxymethyl, 1-imidazolylmethyl, 1,2,4-triazol-1-ylmethyl or 5-methyloxazol-3-yl. 2. A process according to claim 1, wherein the N-propargylanilines of the formula II are: R ^1, R ² and R ⁵ have the abovementioned meaning, are reacted with chloride, bromide, or acid anhydride corresponding to the general formulas IIIa or IIIb, R ⁶ - C - Cl (Br) O (IIIa), (R ⁶ —C) 2 O II o (Illb) in which R ⁶ has the above meanings, in the presence of a diluent and if appropriate in the presence of an acid.