DE3732093A1 - Fungicidal acrylic acid esters - Google Patents

Abstract

Acrylic acid esters of the formula <IMAGE> in which R<1> and R<2> denote hydrogen or alkyl, X (m = 1 to 5) denotes halogen, cyano, trifluoromethyl, nitro, alkyl, alkoxy, phenyl, phenoxy, benzyloxy or hydrogen, and Y denotes methyleneoxy, oxymethylene, ethylene, ethenylene, ethynylene or oxygen, and fungicides containing these compounds.>

Description

The present invention relates to new acrylic acid esters, their preparation and their use as fungicides.

It is known to 2-phenyl-3-methoxy-acrylic acid methyl ester derivatives, e.g. B. the 2- (2-Benzyloxyphenyl) -3-methoxy-acrylic acid methyl ester as a fungicide use (EP-1 78 826). However, their effect is in some cases insufficient.

It has now been found that new acrylic acid esters of the formula

in the
R¹ and R² are identical or different and are hydrogen or alkyl having 1 to 5 carbon atoms,
X (m = 1 to 5) identical or different substituents halogen, cyano, trifluoromethyl, nitro, C₁-C₄-alkyl, C₁-C₄-alkoxy, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted benzyloxy or hydrogen and
Y is methyleneoxy, oxymethylene, ethylene, ethenylene, ethynylene or oxygen,
not only have a very high fungitoxic effect but also have a very good plant tolerance.

Some of the new compounds of formula I fall in the preparation due to the C = C double bond as E / Z isomer mixtures, which in usual way, e.g. B. by crystallization or chromatography in the individual components can be separated. Both the individual Isomeric compounds as well as their mixtures are of the invention includes.

R¹ means for example hydrogen, C₁-C₃-alkyl, methyl, ethyl and Isopropyl, R² is, for example, hydrogen, C₁-C₅-alkyl, methyl, Ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl and neopentyl.  

X _m is, for example, hydrogen, 2-fluorine, 3-fluorine, 4-fluorine, 2-chloro-6-fluorine, 2-chloro, 3-chloro, 4-chloro, 2-bromo, 3-bromo, 4-bromo, 2,4-dichloro, 2,6-dichloro, 3,5-dichloro, 2,4,6-trichloro, 2-chloro-4-methyl, 2 -Methyl-4-chloro, C₁-C₄-alkyl, 2-methyl, 3-methyl, 4-methyl, 4-ethyl, 4-isopropyl, 4-tert-butyl, 2,4 -Dimethyl-, 2,6-dimethyl-, 2,4,6-trimethyl-, 2-methoxy-4-methyl-, 4-methoxy-2-methyl, C₁-C₄-alkoxy, 2-methoxy-, 3- Methoxy, 4-methoxy, 4-ethoxy, 4-isopropoxy, 2-trifluoromethyl, 3-trifluoromethyl, 4-trifluoromethyl, 2-cyano, 4-cyano, 3-nitro, 4- Nitro-, phenyl, 4-phenyl, 4-benzyloxy-, 4-phenoxy, halophenoxy, 4- (2-chloro) -phenoxy-, 4- (2,4-dichloro) -phenoxy-, C₁-C₄-alkylphenoxy, 4- (2-methyl) phenoxy, 3-benzyloxy, halobenzyloxy, 3- (2-chloro) benzyloxy, 3- (2,4-dichloro) benzyloxy, 3- (2- Fluoro) -benzyloxy-, 3- (4-bromo) -benzyloxy-, C₁-C₄-alkylbenzyloxy-, 3- (2-methyl) -benzyloxy-, 3-phenoxy-, 3- (2-chloro) -phenoxy- , 3- (2,4-dichloro) phenoxy-, 3- (2-fluoro) phenoxy-, 3- (4-bromo) -phenoxy, 3- (2-methyl) -phenoxy-, Y is for example a -CH₂O-, -OCH₂-, -CH₂-CH₂-, -CH = CH-, -C≡C- Group or stands for O.

The new compounds can be used, for example, according to the following procedure produce:

2-methylphenylacetic acid ester of the formula II

according to Wislicenus (Liebigs Annalen 424, 215 (1921) and Liebigs Annalen 413, 206 (1917)) with methyl formate and sodium hydride in reacted with an inert solvent. The so obtained Compounds of formula III

are with p-toluenesulfonyl chloride in the presence of a base in one Solvent (e.g. tetrahydrofuran) to the tosylates of formula IV implemented.  

These can be reacted with an alkylthiol of the formula R²SH in the presence of a base or with sodium alkylthiolate in a solvent (e.g. methanol) to give the β- alkylthioacrylic acid esters of the formula V.

The bromination of this compound with N-bromosuccinimide (Horner, Winkelmann, Angew. Chemie 71, 349 (1959)) leads to α - (2-bromomethylphenyl) - β- alkyl thioacrylic acid esters which react with trialkyl phosphates to form phosphonic acid esters of the general formula VI,

in which R¹ and R² have the meanings given above and R³ for C₁-C₈- Alkyl stands (Houben-Weyl, Methods of Organic Chemistry 12/1 433 ff, (1963)).

The phosphonic acid esters are substituted with benzaldehydes in the presence a base in a solvent (e.g. tetrahydrofuran) to the Final products of Formula I implemented:

The unsaturated derivatives thus obtained can either be catalytic with hydrogen (see Houben-Weyl, Methods of Organic Chemistry V / 2b, 264-267 (1981)) or with diimine (cf. Houben-Weyl, methods of organic chemistry IV / Ic, 580 u. E. E. van Tamelen, R. S. Dewey, M. F. Lease, W. H. Pirkle, JACS 83, 4302 (1961)) selectively for new alkylthioacrylic acid esters to reduce:  

The α - (2-bromomethylphenyl) - β- alkylthioacrylic acid esters obtained as precursors can be reacted with phenolates in suitable solvents (e.g. toluene) to give the corresponding end products of the formula I:

Another manufacturing process is e.g. B. The following: The new compounds of formula I can be prepared by an α- ketocarboxylic acid ester of formula VII in a Wittig-Horner reaction in the presence of a base such as sodium hydride or n-butyllithium with a phosphonic acid ester of formula VIII in a suitable solvent (e.g. tetrahydrofuran) (see I. Shakak, J. Almoy, Synthesis, 1969, 170 to 172):

The α- ketocarboxylic acid esters of the formula VII can, for. B. from the corresponding Grignard compounds, for. B.

with imidazolides of the formula IX (J. S. Nimitz, H. S. Mosher, J. Org. Chem., 1981, 46, 211 to 213):

Another manufacturing process is e.g. B. the following: the new ones Compounds of formula I can be prepared by partially already known 3-hydroxyacrylic acid esters of the formula X (cf. EP 2 03 608)

with p-toluenesulfonic acid chloride in the presence of a base in a solvent (e.g. tetrahydrofuran) to the tosylates of the formula XI. These can be with an alkylthiol of the formula R²SH in the presence of a base or with sodium alkyl thiolate in a solvent (e.g. methanol) in the new acrylic acid esters of formula I are converted:

In all formulas, X _m , Y, R 1 and R 2 each have the meanings given above.

The preparation of the new compounds of formula I is as follows Example explained:

Manufacturing example

• a) 72 g (250 mmol) of 2- (2-benzyloxyphenyl) -3-hydroxyacrylic acid methyl ester and 25.8 g (255 mmol) of triethylamine are placed in 200 ml of tetrahydrofuran. 47.5 g (250 mmol) of p-toluenesulfonic acid chloride (dissolved in 100 ml of tetrahydrofuran) are added dropwise with ice cooling. The mixture is stirred in an ice bath for 1 hour and at room temperature for 1 hour. Then the precipitated triethylamine hydrochloride is removed by suction and washed with tetrahydrofuran. After concentration, 108 g (98%) of 2- (2-benzyloxyphenyl) -3- (p-toluenesulfonyloxy) acrylic acid methyl ester are obtained.
  1 H-NMR (CDCl₃): δ = 2.4 (S, 3H), 3.65 (S, 3H), 4.95 (S, 2H), 6.9 (m, 4H), 7.3 (m, 7H), 7.7 (d, 2H) , 7.8 (S, 1H).
• b) 22 g (50 mmol) of tosylate (obtained in (a)) are initially introduced into 300 ml of methanol at room temperature (20 ° C.). A solution of 3.5 g (50 mmol) of sodium thiomethylate in 200 ml of methanol is added dropwise. The mixture is then heated under reflux for 3 hours. After concentration, the residue is taken up in diethyl ether, washed with H₂O, dried over sodium sulfate and concentrated. 14 g (88%) of methyl 2- (2-benzyloxyphenyl) -3-thiomethylacrylate are obtained as resin (compound No. 83 in the table).
  1 H-NMR (CDCl₃): δ = 2.35 (S, 3H), 3.65 (S, 3H), 5.05 (S, 2H), 6.9-7.3 (m, 4H), 7.35 (m, 5H), 7.8 (S, 1H).

The following connections are made in a corresponding manner.  

table

Generally speaking, the new compounds are characterized by a excellent effectiveness against a wide range of phytopathogenic agents Mushrooms, in particular from the classes of the Ascomycetes and Basidiomycetes, out. They are partially systemic and can be used as leaf and Soil fungicides are used.

The fungicidal compounds are particularly interesting for combating a variety of fungi on different crops or their Seeds, especially wheat, rye, barley, oats, rice, corn, lawn, Cotton, soy, coffee, sugar cane, fruit and ornamental plants in horticulture, Viticulture and vegetables - such as cucumbers, beans and squashes -.

The new compounds are particularly suitable for controlling the following plant diseases:
Erysiphe graminis (powdery mildew) in cereals,
Erysiphe cichoracearum and Sphaerotheca fuliginea on pumpkin plants,
Podosphaera leucotricha on apples,
Uncinula necator on vines,
Puccinia species on cereals,
Rhizoctonia species on cotton and lawn,
Ustilago species on cereals and sugar cane,
Venturia inaequalis (scab) on apples,
Helminthosporium species on cereals,
Septoria nodorum on wheat,
Botrytis cinera (gray mold) on strawberries, vines,
Cercospora arachidicola on peanuts,
Pseudocercosporella herpotrichoides on wheat, barley,
Pyricularia oryzae on rice,
Phytophthora infestans on potatoes and tomatoes,
Fusarium and Verticillium species on different plants.
Plasmopara viticola on vines,
Alternaria species on fruits and vegetables.

The compounds are applied by treating the plants with the active ingredients sprayed or dusted or the seeds of the plants with the active ingredients treated. It is used before or after infection Plants or seeds through the mushrooms.

The new substances can be converted into the usual formulations such as solutions, emulsions, suspensions, dusts, powders, pastes and Granules. The application forms depend entirely on the purposes; in any case, they should have a fine and even distribution  ensure the effective substance. The wording is in manufactured in a known manner, e.g. B. by stretching the active ingredient with Solvents and / or carriers, optionally using of emulsifiers and dispersants, where in the case of use of water as a diluent other organic solvents than Auxiliary solvents can be used. As auxiliaries come for it essentially in question: solvents such as aromatics (e.g. xylene), chlorinated aromatics (e.g. chlorobenzenes), paraffins (e.g. petroleum fractions), Alcohols (e.g. methanol, butanol), ketones (e.g. cyclohexanone), amines (e.g. Ethanolamine, dimethylformamide) and water; Carriers like natural Rock flours (e.g. kaolins, clays, talc, chalk) and synthetic Rock flour (e.g. highly disperse silica, silicates); Emulsifier, such as nonionic and anionic emulsifiers (e.g. polyoxyethylene Fatty alcohol ethers, alkyl sulfonates and aryl sulfonates) and dispersants, such as lignin, lye and methyl cellulose.

The fungicidal compositions generally contain between 0.1 and 95, preferably between 0.5 and 90 wt .-% active ingredient.

Depending on the type of effect desired, the application rates are between 0.02 and 3 kg of active ingredient or more per hectare. The new compounds can can also be used in material protection, e.g. B. against Paecilomyces variotii.

Some of the new compounds have very good activity against human pathogenic fungi such as Trichophyton mentagrophytes and Candida albicans.

The agents or the ready-to-use preparations made therefrom, such as solutions, emulsions, suspensions, powders, dusts, pastes or Granules are used in a known manner, for example by Spraying, atomizing, dusting, scattering, pickling or pouring.

Examples of such preparations are:

• I. 90 parts by weight of compound no. 83 are mixed with 10 parts by weight of N-methyl- α- pyrrolidone and a solution is obtained which is suitable for use in the form of tiny drops.
• II. 20 parts by weight of compound no. 83 are mixed dissolved, the 80 parts by weight of xylene, 10 parts by weight of Addition product of 8 to 10 moles of ethylene oxide with 1 mole Oleic acid-N-monoethanolamide, 5 parts by weight of calcium salt  Dodecylbenzenesulfonic acid and 5 parts by weight of the adduct and 40 moles of ethylene oxide with 1 mole of castor oil. Obtained by pouring and finely distributing the solution in water an aqueous dispersion.
• III. 20 parts by weight of compound no. 83 are dissolved in a mixture, that from 40 parts by weight of cyclohexanone, 30 parts by weight Isobutanol, 20 parts by weight of the adduct of 40 moles There is ethylene oxide in 1 mol of castor oil. By pouring and finely distributing the solution in water gives an aqueous Dispersion.
• IV. 20 parts by weight of compound no. 83 are mixed dissolved, the 25 parts by weight of cyclohexanol, 65 parts by weight of one Mineral oil fraction with a boiling point of 210 to 280 ° C and 10 parts by weight of the adduct of 40 moles of ethylene oxide with 1 mole Castor oil is made up. By pouring and finely distributing the Solution in water gives an aqueous dispersion.
• V. 80 parts by weight of compound no. 83 are mixed well with 3 parts by weight of the sodium salt of diisobutylnaphthalene- α- sulfonic acid, 10 parts by weight of the sodium salt of lignosulfonic acid from a sulfite waste liquor and 7 parts by weight of powdered silica gel and ground in a hammer mill. A spray mixture is obtained by finely distributing the mixture in water.
• VI. 3 parts by weight of compound no. 83 are mixed with 97 parts by weight finely divided kaolin mixed intimately. You get this way a dust containing 3% by weight of the active ingredient.
• VII. 30 parts by weight of compound no. 83 are mixed with a mixture of 92 parts by weight of powdered silica gel and 8 parts by weight Paraffin oil that is on the surface of this silica gel was sprayed, mixed intimately. You get one in this way Preparation of the active ingredient with good adhesiveness.
• VIII. 40 parts by weight of compound no. 83 are mixed with 10 parts by weight Sodium salt of a phenolsulfonic acid-urea-formaldehyde condensate, 2 parts by weight of silica gel and 48 parts by weight of water intimately mixed. A stable aqueous dispersion is obtained. By diluting an aqueous dispersion is obtained with water.  
• IX. 20 parts by weight of compound no. 83 are mixed with 2 parts by weight of calcium salt dodecylbenzenesulfonic acid, 8 parts by weight of fatty alcohol polyglycol ether, 2 parts by weight of sodium salt of a phenolsulfonic acid urea-formaldehyde condensate and 68 parts by weight of one paraffinic mineral oil intimately mixed. You get one stable oily dispersion.

The agents according to the invention can also be used together in this application form with other active ingredients, such as. B. herbicides, insecticides, Growth regulators and fungicides, or also with fertilizers are mixed and applied. When mixed with fungicides in many cases the fungicidal activity spectrum is enlarged.

The following list of fungicides with which the compounds of the invention can be combined, the possible combinations explain, but not limit.

Fungicides that can be combined with the compounds according to the invention are, for example:
Sulfur,
Dithiocarbamates and their derivatives, such as
Ferridimethyldithiocarbamate,
Zinc dimethyldithiocarbamate,
Zinc ethylene bisdithiocarbamate,
Manganese ethylene bisdithiocarbamate,
Manganese-zinc-ethylenediamine-bis-dithiocarbamate,
Tetramethylthiuram disulfide,
Ammonia complex of zinc (N, N-ethylene-bis-dithiocarbamate),
Ammonia complex of zinc (N, N'-propylene-bis-dithiocarbamate),
Zinc (N, N'-propylene-bis-dithiocarbamate),
N, N'-polypropylene bis (thiocarbamoyl) disulfide;
Nitroderivatives, such as
Dinitro- (1-methylheptyl) phenylcrotonate,
2-sec-butyl-4,6-dinitrophenyl-3,3-dimethylacrylate,
2-sec-butyl-4,6-dinitrophenyl-isopropyl carbonate;
5-nitro-isophthalic acid di-isopropyl ester;
heterocyclic substances, such as
2-heptadecyl-2-imidazoline acetate,
2,4-dichloro-6- (o-chloroanilino) -s-triazine,
O, O-diethyl phthalimidophosphonothioate,
5-amino-1 [bis- (dimethylamino) phosphinyl] -3-phenyl-1,2,4-triazole,
2,3-dicyano-1,4-dithioanthraquinone,
2-thio-1,3-dithio- (4,5-b) -quinoxaline,
1- (butylcarbamoyl) -2-benzimidazole-carbamic acid methyl ester,
2-methoxycarbonylamino-benzimidazole,
2- (furyl- (2)) - benzimidazole,
2- (thiazolyl- (4)) - benzimidazole,
N- (1,1,2,2-tetrachloroethylthio) tetrahydrophthalimide,
N-trichloromethylthio-tetrahydrophthalimide,
N-trichloromethylthio-phthalimide,
N-dichlorofluoromethylthio-N ′, N′-dimethyl-N-phenyl-sulfuric acid diamide,
5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole,
2-rhodanmethylthiobenzthiazole,
1,4-dichloro-2,5-dimethoxybenzene,
4- (2-chlorophenylhydroazano) -3-methyl-5-isoxazolone,
Pyridine-2-thio-1-oxide,
8-hydroxyquinoline or its copper salt,
2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiine,
2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiin-4,4-dioxide,
2-methyl-5,6-dihydro-4H-pyran-3-carboxylic acid aniline,
2-methyl-furan-3-carboxylic acid anilide,
2,5-dimethyl-furan-3-carboxylic acid anilide,
2,4,5-trimethyl-furan-3-carboxylic acid anilide,
2,5-dimethyl-furan-3-carboxylic acid cyclohexylamide,
N-cyclohexyl-N-methoxy-2,5-dimethyl-furan-3-carboxamide,
2-methylbenzoic acid anilide,
2-iodo-benzoic acid anilide,
N-formyl-N-morpholine-2,2,2-trichloroethyl acetal,
Piperazin-1,4-diylbis- (1- (2,2,2-trichloro-ethyl) -formamide,
1- (3,4-dichloroanilino) -1-formylamino-2,2,2-trichloroethane,
2,6-dimethyl-N-tridecyl-morpholine or its salts,
2,6-dimethyl-N-cyclodedecyl-morpholine or its salts,
N- [3- (p-tert-butylphenyl) -2-methylpropyl] cis-2,6-dimethylmorpholine,
N- [3- (p-tert-butylphenyl) -2-methylpropyl] piperidine,
1- [2- (2,4-dichlorophenyl) -4-ethyl-1,3-dioxolan-2-yl-ethyl] -1H-1,2,4-t-riazole,
1- [2- (2,4-dichlorophenyl) -4-n-propyl-1,3-dioxolan-2-yl-ethyl] -1H-1,2,4-triazole,
N- (n-propyl) -N- (2,4,6-trichlorophenoxyethyl) -N'-imidazol-yl-urea,
1- (4-chlorophenoxy) -3,3-dimethyl-1- (1H-1,2,4-triazol-1-yl) -2-butanone, -
1- (4-chlorophenoxy) -3,3-dimethyl-1- (1H-1,2,4-triazol-1-yl) -2-butanol, -
α - (2-chlorophenyl) - α - (4-chlorophenyl) -5-pyrimidine-methanol,
5-butyl-2-dimethylamino-4-hydroxy-6-methyl-pyrimidine,
Bis- (p-chlorophenyl) -3-pyridinemethanol,
1,2-bis (3-ethoxycarbonyl-2-thioureido) benzene,
1,2-bis (3-methoxycarbonyl-2-thioureido) benzene,
as well as various fungicides, such as
Dodecylguanidine acetate,
3- [3- (3,5-dimethyl-2-oxycyclohexyl) -2-hydroxyethyl] glutarimide,
Hexachlorobenzene,
DL-methyl-N- (2,6-dimethyl-phenyl) -N-furoyl (2) -alaninate,
DL-N- (2,6-dimethylphenyl) -N- (2'-methoxyacetyl) alanine methyl ester,
N- (2,6-dimethylphenyl) -N-chloroacetyl-D, L-2-aminobutyrolactone,
DL-N- (2,6-dimethylphenyl) -N- (phenylacetyl-alanine methyl ester,
5-methyl-5-vinyl-3- (3,5-dichlorophenyl) -2,4-dioxo-1,3-oxazolidine,
3- [3,5-dichlorophenyl (-5-methyl-5-methoxymethyl] -1,3-oxazolidine-2,4-d-ion,
3- (3,5-dichlorophenyl) -1-isopropylcarbamoylhydantoin,
N- (3,5-dichlorophenyl) -1,2-dimethylcyclopropane-1,2-dicarboximide, -
2-cyano- [N- (ethylaminocarbonyl) -2-methoximino] acetamide,
1- [2- (2,4-dichlorophenyl) pentyl] -1H-1,2,4-triazole,
2,4-difluoro- α - (1H-1,2,4-triazolyl-1-methyl) -benzhydryl alcohol,
N- (3-chloro-2,6-dinitro-4-trifluoromethyl-phenyl) -5-trifluoromethyl-3-chloro-2-aminopyridine,
1 - ((bis- (4-Fluorophenyl) methylsilyl) methyl) -1H-1,2,4-triazole.

Examples of use

The comparative active ingredient was 2- (2-benzyloxyphenyl) -3-methoxy-acrylic acid methyl ester (A) - known from EP 1 78 826 - used.

Application example 1 Efficacy against botrytis cinerea on peppers

Pepper seedlings of the variety "Neusiedler Ideal Elite" were after themselves 4-5 leaves had developed well, with aqueous suspensions that were 80% Active ingredient and 20% emulsifier contained in the dry substance, sprayed soaking wet. After the spray coating had dried on, the Plants with a conidia suspension of the botrytis cinerea fungus sprayed and at 22 to 24 ° C in a chamber with high humidity posed. After 5 days the disease had spread to the untreated Control plants developed so strongly that the resulting leaf necrosis covered most of the leaves.  

The result shows that the active ingredient 83 when used as 0.05% (% By weight) spray liquor shows a better fungicidal activity (90%) than that known comparative drug A (50%).

Claims (6)

1. Acrylic acid ester of the formula in the
R¹ and R² are identical or different and are hydrogen or alkyl having 1 to 5 carbon atoms,
X (m = 1 to 5) are identical or different substituents halogen, cyano, trifluoromethyl, nitro, C₁-C₄-alkyl, C₁-C4-alkoxy, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted benzyloxy or hydrogen and
Y means methyleneoxy, oxymethylene, ethylene, ethenylene, ethynylene or oxygen. 2. Compounds of formula I according to claim 1, in which X _{m is} hydrogen, 2-fluoro, 3-fluoro, 4-fluoro, 2-chloro-6-fluoro, 2-chloro, 3-chloro, 4-chloro, 2-bromo, 3-bromo, 4-bromo, 2,4-dichloro, 2,6-dichloro, 3,5-dichloro, 2,4,6-trichloro, 2-chloro-4-methyl, 2-methyl-4-chloro, 2-methyl, 3-methyl, 4-methyl, 4-ethyl, 4-isopropyl, 4-tert-butyl , 2,4-dimethyl, 2,6-dimethyl, 2,4,6-trimethyl, 2-methoxy-4-methyl, 4-methoxy-2-methyl, 2-methoxy, 3-methoxy , 4-methoxy, 4-ethoxy, 4-isopropoxy, 2-trifluoromethyl, 3-trifluoromethyl, 4-trifluoromethyl, 2-cyano, 4-cyano, 3-nitro, 4-nitro , 4-phenyl, 4-benzyloxy-, 4-phenoxy, halophenoxy, 4- (2-chloro) -phenoxy-, 4- (2,4-dichloro) -phenoxy-, C₁-C₄-alkylphenoxy, 4- (2nd -Methyl) -phenoxy-, 3-benzyloxy-, halobenzyloxy-, 3- (2-chloro) -benzyloxy-, 3- (2,4-dichloro) -benzyloxy-, 3- (2-fluoro) -benzyloxy -, 3- (4-bromo) -benzyloxy-, C₁-C₄-alkylbenzyloxy-, 3- (2-methyl) -benzyloxy-, 3-phenoxy-, 3- (2-chloro) -phenoxy-, 3- ( 2,4-dichloro-phenoxy-, 3- (2-fluoro) -phen oxy-, 3- (4-bromo) -phenoxy, 3- (2-methyl) -phenoxy-, R¹ hydrogen, methyl, ethyl, isopropyl, R² hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl or neopentyl and Y is -CH₂O-, -OCH₂-, -CH₂-CH₂-, -CH = CH-, -C≡C group or O means. 3. Fungicidal composition comprising a fungicidally effective amount of a compound of the formula in the
R¹ and R² are identical or different and are hydrogen or alkyl having 1 to 5 carbon atoms,
X (m = 1 to 5) identical or different substituents halogen, cyano, trifluoromethyl, nitro, C₁-C₄-alkyl, C₁-C₄-alkoxy, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted benzyloxy or hydrogen and
Y is methyleneoxy, oxymethylene, ethylene, ethenylene or oxygen,
and a liquid or solid carrier. 4. Process for combating fungi, characterized in that an fungicidally effective amount of a compound of the formula in the
R¹ and R² are identical or different and are hydrogen or alkyl having 1 to 5 carbon atoms,
X (m = 1 to 5) identical or different substituents halogen, cyano, trifluoromethyl, nitro, C₁-C₄-alkyl, C₁-C₄-alkoxy, optionally substituted phenyl, optionally substituted phenoxy, optionally substituted benzyloxy or hydrogen and
Y means methyleneoxy, oxymethylene, ethylene, ethenylene, ethynylene or oxygen
can act on the fungi or on areas, plants, materials or seeds threatened by fungal attack. 5. A process for the preparation of a fungicidal agent, characterized in that that one with a compound of formula I according to claim 1 a solid or liquid carrier and optionally with a or several surfactants. 6. 2- (2-Benzyloxyphenyl) -3-thiomethyl-acrylic acid methyl ester.