DE2841824A1 - ACETIC ACID ANILIDE, METHOD FOR PRODUCING THESE COMPOUNDS, AND THIS FUNGICIDAL CONTAINER - Google Patents

Description

The invention relates to new acetic anilides, a process for the preparation of these compounds and a fungicidal agent for combating phytopathogenic fungi containing at least one of these compounds.

Means for combating phytopathogenic fungi are already known. Agents of this type known in practice are, for example, tetramethylthiuramide disulfide (DE-PS 642 532) and manganese-ethylene bisdithiocarbamate (US-PS 2,504,404).

The object of the present invention is to develop new fungicides with good action against leaf and soil fungi.

According to the invention, this object is achieved by an agent which is characterized in that it contains at least one compound of the general formula I.

contains, in the

R [deep] 1 hydrogen or C [deep] 1-C [deep] 4-alkyl,

R [deep] 2 is an aromatic hydrocarbon radical or one or more than one, identical or different through C [deep] 1-C [deep] 4-alkyl, C [deep] 1-C [deep] 4-alkoxy, C [deep ] 1-C [deep] 4-alkylthio, halogen, trifluoromethyl, nitro, C [deep] 1-C [deep] 4-alkoxycarbonyl or cyano substituted aromatic hydrocarbon radical,

R [deep] 3 C [deep] 1-C [deep] 6-alkyl, halogen-C [deep] 1-C [deep] 6-alkyl, C [deep] 1-C [deep] 4-alkoxy-C [deep] 1-C [deep] 4-alkyl, C [deep] 2-C [deep] 6-alkenyl, C [deep] 3-C [deep] 6-alkynyl, C [deep] 1-C [deep ] 6-alkylcarbonyl, halogen-C [deep] 1-C [deep] 6-alkylcarbonyl, single or multiple, identical or different through halogen, C [deep] 1-C [deep] 4-alkyl, C [deep] 1-C [deep] 4-alkoxy, C [deep] 1-C [deep] 4-alkylthio, trifluoromethyl, nitro or amino substituted phenyl or benzyl, the amidino or dimethylthiocarbamoyl group and

X is oxygen, sulfur, the sulfinyl or sulfonyl group.

The compounds according to the invention are surprisingly superior to the known agents of the above-mentioned type in their action against phytopathogenic fungi and, moreover, are well tolerated by plants and have a sufficient duration of action. They do not have a phytotoxic effect in the practically applicable application rates, so that negative effects on plant growth are excluded when they are used. Thanks to these advantageous properties, these compounds can therefore be used in agriculture or in horticulture be used for soil and soil treatment or for leaf application.

The compounds according to the invention are distinguished by an excellent action against a large number of harmful fungi, such as, for example, Pythium, Phytophthora, Plasmopara, Piricularia, Botrytis and others.

In contrast to the only preventively active agents, such as, for example, manganese ethylene bisdithiocarbamate, the compounds according to the invention have the extraordinary advantage of a curative and systemic effect and thus also allow the control of fungi which have already penetrated the plants.

Of the compounds according to the invention, particularly those in which in the formula I given above are distinguished by a very good action

R [deep] 1 hydrogen, methyl or ethyl,

R [deep] 2 phenyl, methylphenyl, dimethylphenyl, methoxyphenyl, fluorophenyl, chlorophenyl, bromophenyl, dichlorophenyl, trifluoromethylphenyl, methylthiophenyl or cyanophenyl,

R [deep] 3 methyl, ethyl, propyl, isopropyl, tert-butyl, allyl, propenyl, propynyl, methoxyethyl, benzyl, chlorobenzyl, methylbenzyl, methoxybenzyl, phenyl, chlorophenyl, methylphenyl, methoxyphenyl, acetyl, chloroacetyl and

X denotes oxygen, sulfur, the sulfinyl or the sulfonyl group.

The compounds according to the invention can be used either alone, in a mixture with one another or with other active ingredients. If desired, other fungicides, nematicides, insecticides or other pesticides - depending on the desired purpose - can be added.

The active ingredients are expediently in the form of preparations, such as, for example, powders, scattering agents, granules, solutions, emulsions or suspensions, with the addition of liquid and / or solid carriers or diluents and optionally wetting agents, adhesives, emulsifying agents and / or dispersing agents applied.

Suitable liquid carriers are water, mineral oils, or other organic solvents such as xylene, chlorobenzene, cyclohexanol, dioxane, acetonitrile, ethyl acetate, dimethylformamide, isophorone and dimethyl sulfoxide.

Lime, kaolin, circles, talc, attaclay and other clays as well as natural or synthetic silica are suitable as solid carriers.

Examples of surface-active substances are: salts of lignin sulfonic acids, salts of alkylated benzenesulfonic acids, sulfonated acid amides and their salts, polyethoxylated amines and alcohols.

If the active ingredients are to be used for seed dressing, dyes can also be added in order to give the dressed seed a clearly visible color.

The proportion of the active ingredient (s) in the mean can vary within wide limits, the exact concentration of the active ingredient used for the means mainly depending on the amount in which the means are to be used. For example, the agents contain between about 1 to 80 percent by weight, preferably between 20 and 50 percent by weight of active ingredient and about 99 to 20 percent by weight of liquid or solid carriers and optionally up to 20 percent by weight of surface-active substances.

The agents can be applied in the usual way, for example by spraying, atomizing, atomizing, dusting, gasifying, smoking, scattering, pouring or pickling.

The new compounds according to the invention can be prepared, for example, by adding compounds of the general formula II

with acid halides of the general formula

Hal - CO - CH [deep] 2 - X - R [deep] 3 III

optionally dissolved in an organic solvent in the presence of an acid acceptor and the process products are isolated in a manner known per se, where R [deep] 1, R [deep] 2, R [deep] 3 and X have the meaning given above and Hal represents a halogen atom, preferably a chlorine atom.

If X is sulfur, the compound according to the invention can also be prepared by first treating the compounds of the general formula II with acid halides of the general formula

Hal - CO - CH [deep] 2 - Hal IV

optionally in the presence of an acid acceptor, dissolved in an organic solvent, to give compounds of the general

formula V

are implemented, which you then with compounds of the general formula or with thiourea of the formula reacted in an inert organic solvent under nitrogen to give the desired process products, where R [deep] 1, R [deep] 2 and R [deep] 3 have the meaning given above, B is an alkali metal atom, preferably sodium, and Hal is a halogen atom, preferably Chlorine.

Acid acceptors which can optionally be used are, for example, organic bases, such as pyridine, triethylamine or N, N-dimethylaniline, or inorganic bases, such as hydroxides, oxides and carbonates of alkali and alkaline earth metals.

Organic solvents can be used as solvents, such as ether, tetrahydrofuran, benzene, toluene, xylene, ethyl acetate, acetonitrile, dimethylformamide or dimethyl sulfoxide. The reactions are expediently carried out at temperatures between -15.degree. C. and 150.degree.

In the event that X represents the sulfinyl or sulfonyl group, the compounds of the general formula I according to the invention with X meaning sulfur with oxidizing agents such as organic peracids, for example 3-chloroperbenzoic acid, in an inert organic solvent such as methyl chloride or chloroform , or with inorganic reagents such as hydrogen peroxide or potassium permanganate, reacted in acetic acid at temperatures between 0 and 100 ° C. About 2 oxidation equivalents are required to prepare the sulfinyl compounds and, in the case of the sulfonyl compounds, about 4 oxidation equivalents.

The following examples illustrate the preparation of the compounds according to the invention.

EXAMPLE 1

Methoxyacetic acid [2,6-dimethyl-N- (2-oxoperhydro-3-furyl) anilide]

A mixture of 9.75 g (0.047 mol) of 3- (2,6-dimethylanilino) -perhydrofuran-2, 6.50 g (0.06 mol) of methoxyacetyl chloride, 250 ml of toluene and 2 ml of dimethylformamide is added for 3 hours

25 ° C and then stirred for one hour at boiling temperature. It is then concentrated to dryness in vacuo and the solid residue is digested with diisopropyl ether. After the crystals have been filtered off with suction, drying is carried out at 25 ° C. in vacuo.

Yield: 11.5 g = 88% of theory

M.p .: 130-131 ° C

EXAMPLE 2

Acetoxyacetic acid [2,6-dimethyl-N- (2-oxoperhydro-3-furyl) anilide]

10.26 (0.05 mol) 3- (2,6-dimethylanilino) -perhydrofuran-2-dissolved in 200 ml of toluene are mixed with 6.85 g (0.05 mol) of acetoxyacetic acid chloride and heated to the boil for one hour. The reaction solution is then concentrated to dryness in vacuo. The remaining oil is crystallized by rubbing with ether. The crystals are filtered off with suction, washed several times with a little ether and the substance is dried at about 25 ° C. in a vacuum.

Yield: 12.64 g = 82.8% of theory

M.p .: 106-108 ° C

EXAMPLE 3

Methylthioacetic acid [2,6-dimethyl-N- (2-oxoperhydro-3-furyl) anilide]

28.17 g (0.1 mol) of chloroacetic acid [2,6-dimethyl-N- (2-oxoperhydro-3-furyl) anilide] are dissolved in 120 ml of acetonitrile and mixed with 6.5 g (0.15 mol ) Sodium methylate added. The mixture is cooled to about -15 ° C. and 22.4 g (0.47 mol) of methyl mercaptan are added while stirring. After slowly warming to 20 ° C to 25 ° C, the mixture is stirred for about 20 hours at this temperature. It is then taken up with ethyl acetate / water and the alkaline water phase is separated off. The organic phase is extracted once with sodium hydroxide solution and then washed neutral. The ethyl acetate phase is dried over magnesium sulfate, filtered off and concentrated in vacuo. The oily residue is dried in an oil pump vacuum.

Yield: 18 g = 61.3% of theory

M.p .: 71-73 ° C

EXAMPLE 4

Isopropylsulfonyl-acetic acid [2,6-dimethyl-N- (2-oxoperhydro-3-furyl) anilide]

9.64 g (0.03 mol) of isopropylthio-acetic acid [2,6-dimethyl-N- (2-oxoperhydro-3-furyl) anilide] are dissolved in 260 ml of chloroform and mixed with 12.08 g (0, 07 mol) 3-chloroperbenzoic acid added. After stirring for 4 hours at room temperature, a further 6 g (0.035 mol) of 3-chloroperbenzoic acid are added. The mixture is stirred for about 14 hours and the organic phase is extracted several times with 1N sodium hydroxide solution, dried over magnesium sulfate and concentrated in vacuo. The crystals obtained are digested with isoether and filtered off with suction.

Yield: 9 g = 84.9% of theory

M.p .: 177-185 ° C

EXAMPLE 5

Dimethyldithiocarbamic acid [2,6-dimethyl-N- (2-oxoperhydro-3-furyl) anilinocarbonylmethyl] ester

8.45 g (0.03 mol) of chloroacetic acid [2,6-dimethyl-N- (2-oxoperhydro-3-furyl) -anild] are dissolved in 100 ml of acetonitrile and, after the addition of 5.3 g (0.037 mol ) Sodium dimethyldithiocarbamate heated to boiling for 6 hours while passing nitrogen through. After cooling to about 20-25 ° C., the reaction mixture is poured into 400 ml of water and extracted 3 times with chloroform. The combined chloroform phases are dried over magnesium sulfate and concentrated in vacuo. The crystalline residue is filtered off with suction, washed with methanol and dried in vacuo at room temperature.

Yield: 7.7 g = 70% of theory

M.p .: 153-156 ° C

The following compounds according to the invention can be prepared analogously.

Name of the connection. Physical constant

________________________________________________________________________________________

Methoxyacetic acid [3-chloro-N- (2-oxoper-

hydro-3-furyl) anilide] m.p .: 100-103 ° C

Methoxyacetic acid- [2,6-dimethyl-N- (5-

methyl-2-oxoperhydro-3-furyl) anilide] M.p .: 113-114 ° C

Methoxyacetic acid [N- (2-oxoperhydro-

3-furyl) anilide] m.p .: 65-66 ° C

Methoxyacetic acid [3-methyl-N- (2-oxoper-

hydro-3-furyl) anilide] m.p .: 115-116 ° C

Methoxyacetic acid [2,3-dimethyl-N- (2-

oxoperhydro-3-furyl) anilide] m.p .: 105-106 ° C

Methoxyacetic acid [3-fluoro-N- (5-methyl-

2-oxoperhydro-3-furyl) anilide] M.p .: 75-76 ° C

Methoxyacetic acid [3-chloro-N- (5-methyl-

2-oxoperhydro-3-furyl) anilide] m.p .: 81-83 ° C

Methoxyacetic acid [2-methyl-N- (2-oxoper-

hydro-3-furyl) anilide] m.p .: 66-67 ° C

Methoxyacetic acid [2-methoxy-N- (2-oxoper-

hydro-3-furyl) anilide] m.p .: 95-97 ° C

Methoxyacetic acid [3-chloro-2-methyl-N- (2-

oxoperhydro-3-furyl) anilide] m.p .: 106-108 ° C

Methoxyacetic acid [3-cyano-N- (2-oxoper-

hydro-3-furyl) anilide] m.p .: 93-94 ° C

Acetoxyacetic acid [3-methyl-N- (2-oxoper-

hydro-3-furyl) anilide] m.p .: 99-103 ° C

Acetoxyacetic acid [N- (2-oxoperhydro-

3-furyl) anilide] m.p .: 127-128 ° C

Acetoxyacetic acid [3-bromo-N- (2-oxo-

perhydro-3-furyl) anilide] m.p .: 137-138 ° C

Acetoxyacetic acid [2,3-dimethyl-N- (2-

oxoperhydro-3-furyl) anilide] m.p .: 97-98 ° C

Acetoxyacetic acid [3-fluoro-N- (2-oxo-

perhydro-3-furyl) anilide] m.p .: 96-98 ° C

Name of the connection. Physical constant

________________________________________________________________________________________

Acetoxyacetic acid- [2,6-dimethyl-N- (5-

methyl-2-oxoperhydro-3-furyl) anilide] M.p .: 140-141 ° C

Acetoxyacetic acid [2-methyl-N- (2-oxo-

perhydro-3-furyl) anilide] m.p .: 119-120 ° C

Acetoxyacetic acid [3-chloro-N- (2-oxo-

perhydro-3-furyl) anilide] m.p .: 123-124 ° C

Acetoxyacetic acid [3-cyano-N- (2-oxo-

perhydro-3-furyl) anilide] m.p .: 118-120 ° C

Phenylthio-acetic acid- [2,6-dimethyl-N-

(2-oxoperhydro-3-furyl) anilide] M.p .: 103-105 ° C

Ethylthio-acetic acid- [2,6-dimethyl-N- (2-

oxoperhydro-3-furyl) anilide] n [deep] D20 1.5552

Isopropylthio-acetic acid- [2,6-dimethyl-N-

(2-oxoperhydro-3-furyl) anilide] n [deep] D20 1.5490

tert-buthylthio-acetic acid [2,6-dimethyl-

N- (oxoperhydro-3-furyl) anilide] n [deep] D20 1.5400

S- [3-chloro-N- (2-oxoperhydro-3-furyl) -anilino-

carbonylmethyl] thiuronium chloride m.p .: 190 ° C (decomposition)

Dimethyldithiocarbamic acid- [3-chloro-N- (2-

oxoperhydro-3-furyl) -anilino-carbonylmethyl] -

ester m.p .: 126 ° C

Dimethylthiocarbamic acid [3-fluoro-N- (2-oxo-

perhydro-3-furyl) anilinocarbonylmethyl] -

ester m.p .: 160-61 ° C

(3-methylphenylthio) -3-acetic acid- [2,6-di-

methyl-N- (2-oxoperhydro-3-furyl) anilide] n [deep] D20 1.5950

(Benzylthio) acetic acid [2,6-dimethyl-N-

(2-oxoperhydro-3-furyl) anilide] n [deep] D20 1.5720

(2-aminophenylthio) acetic acid [2,6-di-

methyl-N- (2-oxoperhydro-3-furyl) anilide] M.p .: 150-151 ° C

Chloroacetoxyacetic acid [2,6-dimethyl-N-

(2-oxoperhydro-3-furyl) anilide] M.p .: 115-118 ° C

Name of the connection. Physical constant

________________________________________________________________________________________

Phenoxyacetic acid- [2,6-dimethyl-N-

(2-oxoperhydro-3-furyl) anilide] M.p .: 92-93 ° C

Chloroacetoxyacetic acid- [N- (2-oxoper-

hydro-3-furyl) anilide] m.p .: 64 ° C

Chloroacetoxyacetic acid [3-methyl-N- (2-

oxoperhydro-3-furyl) anilide] m.p .: 82-83 ° C

Chloroacetoxyacetic acid [3-bromo-N- (2-

oxoperhydro-3-furyl) anilide] m.p .: 124-125 ° C

Phenoxyacetic acid [3-bromo-N- (2-oxo-

perhydro-3-furyl) anilide] m.p .: 114 ° C

Phenoxyacetic acid [N- (2-oxoperhydro-

3-furyl) anilide] m.p .: 120-121 ° C

Phenoxyacetic acid- [2,3-dimethyl-N- (2-

oxoperhydro-3-furyl) anilide] m.p .: 80-82 ° C

Phenoxyacetic acid [3-methyl-N- (2-oxo-

perhydro-3-furyl) anilide] m.p .: 87-89 ° C

Phenoxyacetic acid [2-methyl-N- (2-oxo-

perhydro-3-furyl) anilide] m.p .: 112-113 ° C

Phenoxyacetic acid [3-chloro-N- (2-oxo-

perhydro-3-furyl) anilide] m.p .: 93-95 ° C

Chloroacetoxyacetic acid- [3-chloro-N- (2-

oxoperhydro-3-furyl) anilide] m.p .: 102-103 ° C

Phenoxyacetic acid- [2,6-dimethyl-N- (5-

methyl-2-oxoperhydro-3-furyl) anilide] M.p .: 142-143 ° C

Chloroacetoxyacetic acid [2,6-dimethyl-N-

(5-methyl-2-oxoperhydro-3-furyl) anilide] M.p .: 94-97 ° C

S- [2,6-dimethyl-N- (2-oxoperhydro-3-furyl) -

anilinocarbonylmethyl] thiuronium chloride mp .: 260 ° C (decomposition)

The compounds according to the invention are generally almost colorless, odorless, crystalline bodies or slightly yellowish liquids, which are very poor in water and gasoline, in polar solvents such as acetone, dimethylformamide and dimethyl sulfoxide, however, are very soluble.

The starting compounds for the preparation of the compounds according to the invention are known per se or can be prepared by processes known per se.

The following examples serve to illustrate the possible uses and the superior fungicidal action of the compounds according to the invention.

EXAMPLE 6

Limit concentration test in the fight against Pythium ultimum

20% powdery active ingredient preparations were evenly mixed with the soil which was heavily contaminated by Pythium ultimum. The treated soil was filled into clay bowls with a capacity of 0.5 liters and, without a waiting period, 20 seeds of peas (Pisum sativum L. convar. Medullare Alef.) Of the "Wunder von Kelvedon" variety were sown per bowl. After a cultivation period of 3 weeks at 20-24 ° C in the greenhouse, the number of healthy peas was determined and a root rating (1-4) was carried out.

Active ingredients, application rates and results are listed in the table below.

Root rating: 4 = white roots without fungal necrosis

3 = white roots, slight fungal necrosis

2 = brown roots, already stronger fungal necrosis

1 = severe fungal necrosis, rotten roots

EXAMPLE 7

Control of Phytophthora nicotianae var. Nicotianae in the pot culture of Sinningia speciosa

Sinningia young plants of the "Berliner Rot" variety were potted in clay pots with a diameter of 11 cm. The pot substrate was a mixture of 1 part peat culture substrate and 1 part compost soil. After potting, the plants were watered once with 100 ml of the specified preparation concentration. 3 days later, the pots were uniformly inoculated with mycelium flakes from a 3-week-old Phytophthora culture. This was followed by a culture period of 7 weeks at 22 to 24 ° C in the greenhouse.

Active ingredients, application rates and results are listed in the table below.

EXAMPLE 8

Control of Phytophthora parasitica var. Nicotianae in tobacco culture

Young tobacco plants of the "Havana" variety were potted into clay pots with a diameter of 14 cm. The potting substrate was a mixture of 1 part peat culture substrate and 1 part sandy compost soil. After potting, the plants were watered once with 100 ml of the specified preparation concentration. 3 days later, the pots were inoculated uniformly with mycelium flakes from a 4-week-old Phytophthora culture. This was followed by a culture period of 4 weeks at 24 to 26 ° C in the greenhouse.

Active ingredients, application rates and results are listed in the table below.

EXAMPLE 9

Combating Phytophthora capsici in pepper culture (Capsicum annuum)

Paprika juveniles were potted in clay pots 14 cm in diameter. The substrate was a mixture of 1 part of peat culture substrate with 1 part of sandy compost soil. 3 days after potting, the plants were watered once with 100 ml of the specified preparation concentration. 3 days later, the pots were inoculated uniformly with mycelium flakes from a 4-week-old Phytophthora culture. This was followed by a culture period of 4 weeks at 24 to 26 ° C in the greenhouse.

Active ingredients, application rates and results are listed in the table below.

EXAMPLE 10

Control of Phytophthora cryptogaea in the pot culture of Senecio cruentus

Cineraria young plants of the "Erfurt dwarf" variety were potted in clay pots with a diameter of 11 cm. The potting substrate was a mixture of 1 part peat culture substrate with 1 part sandy compost soil. 3 days after potting, the plants were uniformly inoculated with mycelium flakes from a 3-week-old Phytophthora culture. It filt a culture time of 7 weeks at 20 to 22 ° C in the greenhouse.

Active ingredients, application rates and results are listed in the table below.

EXAMPLE 11

Dressing of French bean seeds

Bush bean seed (Phaseolus vulgaris var. Nanus) of the "wax best of all" variety was dressed with 20% powdered active ingredient preparations. Clay bowls (20x20x5cm) containing 2 liters of earth were filled with normal compost soil (damping-off) and 25 grains of bean seeds were sown per bowl. After a culture period of 15 days at 19 to 21 ° C. in the greenhouse, the healthy seedlings were determined.

Active ingredients, application rate and results are listed in the table below.

Example 12

Effect of prophylactic foliar treatment against Plasmopara viticola on grapevine plants in the greenhouse

Young grapevine plants with about 5 to 8 leaves were sprayed to runoff with an active ingredient concentration of 0.025%, after the spray coating had dried on with an aqueous suspension of sporangia of the fungus (about 20,000 per ml), and immediately sprayed in the greenhouse at 22 to 24 ° C and, if possible, an atmosphere saturated with water vapor.

From the second day on, the humidity was reduced to normal for 3 to 4 days (30 to 70% saturation) and then kept at water vapor saturation for one day. The percentage of fungicidal area was then noted for each leaf and the average per treatment to determine the fungicidal effect was calculated as follows:

Compounds according to the invention% activity

Methoxyacetic acid [2,6-dimethyl-N- (2-

oxoperhydro-3-furyl) anilide] 100

Methoxyacetic acid [3-chloro-N- (2-oxo-

perhydro-3-furyl) anilide] 100

Methoxyacetic acid- [2,6-dimethyl-N- (5-

methyl-2-oxoperhydro-3-furyl) anilide] 100

Methoxyacetic acid [N- (2-oxoperhydro-

3-furyl) anilide] 100

Methoxyacetic acid [3-methyl-N- (2-oxo-

perhydro-3-furyl) anilide] 100

Methoxyacetic acid [2,3-dimethyl-N- (2-

oxoperhydro-3-furyl) anilide] 100

Methoxyacetic acid [3-fluoro-N- (5-methyl-

2-oxoperhydro-3-furyl) anilide] 100

Methoxyacetic acid [3-chloro-N-5-methyl-

2-oxoperhydro-3-furyl) anilide] 100

Acetoxyacetic acid- [2,6-dimethyl-N- (5-

methyl-2-oxoperhydro-3-furyl) anilide] 74

Phenylthioacetic acid [2,6-dimethyl-N-

(2-oxoperhydro-3-furyl) anilide] 98

Acetoxyacetic acid [2-methyl-N- (2-oxo-

perhydro-3-furyl) anilide] 74

Acetoxyacetic acid [2,6-dimethyl-N- (2-

oxoperhydro-3-furyl) anilide] 100

Methoxyacetic acid [2-methyl-N- (2-oxoper-

hydro-3-furyl) anilide] 100

Methoxyacetic acid [2-methoxy-N- (2-oxoper-

hydro-3-furyl) anilide] 100

Methoxyacetic acid [3-chloro-2-methyl-N-

(2-oxoperhydro-3-furyl) anilide] 100

Acetoxyacetic acid [3-chloro-N- (2-oxoper-

hydro-3-furyl) anilide] 98

Compounds according to the invention% active ingredient

Acetoxyacetic acid [3-cyano-N- (2-oxoper-

hydro-3-furyl) anilide] 74

Methoxyacetic acid [3-cyano-N- (2-oxoper-

hydro-3-furyl) anilide] 100

Ethylthio-acetic acid- [2,6-dimethyl-N- (2-

oxoperhydro-3-furyl) anilide] 100

Isopropylthio-acetic acid- [2,6-dimethyl-N-

(2-oxoperhydro-3-furyl) anilide] 100

tert-butylthio-acetic acid- [2,6-dimethyl-N-

(2-oxoperhydro-3-furyl) anilide] 95

Isopropylsulfonyl-acetic acid- [2,6-dimethyl-

N- (2-oxoperhydro-3-furyl) anilide] 100

Claims (58)

1. Acetic anilides of the general formula I, in the R [deep] 1 hydrogen or C [deep] 1-C [deep] 4-alkyl, R [deep] 2 is an aromatic hydrocarbon radical or one or more than one, identical or different through C [deep] 1-C [deep] 4-alkyl, C [deep] 1-C [deep] 4-alkoxy, C [deep ] 1-C [deep] 4-alkylthio, halogen, trifluoromethyl, nitro, C [deep] 1-C [deep] 4-alkoxycarbonyl or cyano substituted aromatic hydrocarbon radical, R [deep] 3 C [deep] 1-C [deep] 6-alkyl, halogen-C [deep] 1-C [deep] 6-alkyl, C [deep] 1-C [deep] 4-alkoxy-C [deep] 1-C [deep] 4-alkyl, C [deep] 2-C [deep] 6-alkenyl, C [deep] 3-C [deep] 6-alkynyl, C [deep] 1-C [deep ] 6-alkylcarbonyl, halogen-C [deep] 1-C [deep] 6-alkylcarbonyl, single or multiple, identical or different through halogen, C [deep] 1-C [deep] 4-alkyl, C [deep] 1-C [deep] 4-alkoxy, C [deep] 1-C [deep] 4-alkylthio, trifluoromethyl, nitro or amino substituted phenyl or benzyl, the amidino or dimethylthiocarbamoyl group and X is oxygen, sulfur, the sulfinyl or sulfonyl group. 2. Acetic acid amides according to claim 1, wherein R [deep] 1 is hydrogen, methyl or ethyl, R [deep] 2 is phenyl, methylphenyl, dimethylphenyl, methoxyphenyl, fluorophenyl, chlorophenyl, dichlorophenyl, trifluoromethylphenyl, methylthiophenyl or cyanophenyl, R [deep] 3 methyl, ethyl, propyl, isopropyl, tert-butyl, allyl, propenyl, propynyl, methoxyethyl, benzyl, chlorobenzyl, methylbenzyl, methoxybenzyl, acetyl, chloroacetyl and X oxygen, sulfur, the sulfinyl or sufonyl group. 3. Methoxyacetic acid [2,6-dimethyl-N- (2-oxoperhydro-3-furyl) anilide]. 4. Acetoxyacetic acid [2,6dimethyl-N- (2-oxoperhydro-3-furyl) anilide]. 5. Methylthio-acetic acid [2,6-dimethyl-N- (2-oxoperhydro-3-furyl) anilide]. 6. Dimethyldithiocarbamic acid [2,6-dimethyl-N- (2-oxoperhydro-3-furyl) anilinocarbonylmethyl] ester. 7. Methoxyacetic acid [3-chloro-N- (2-oxoperhydro-3-furyl) anilide]. 8. Methoxyacetic acid [2,6-dimethyl-N- (5-methyl-2-oxoperhydro-3-furyl) anilide]. 9. Methoxyacetic acid [N- (2-oxoperhydro-3-furyl) anilide]. 10. Methoxyacetic acid [3-methyl-N- (2-oxoperhydro-3-furyl) anilide]. 11. Methoxyacetic acid [2,3-dimethyl-N- (2-oxoperhydro-3-furyl) anilide]. 12. Methoxyacetic acid [3-fluoro-N- (5-methyl-2-oxoperhydro-3-furyl) anilide]. 13. Methoxyacetic acid [3-chloro-N- (5-methyl-2-oxoperhydro-3-furyl) anilide]. 14. Methoxyacetic acid [2-methyl-N- (2-oxoperhydro-3-furyl) anilide]. 15. Methoxyacetic acid [2-methoxy-N- (2-oxoperhydro-3-furyl) anilide]. 16. Methoxyacetic acid [3-chloro-2-methyl-N- (2-oxoperhydro-3-furyl) anilide]. 17. Methoxyacetic acid [3-cyano-N- (2-oxoperhydro-3-furyl) anilide]. 18. Acetoxyacetic acid [3-methyl-N- (2-oxoperhydro-3-furyl) anilide]. 19. Acetoxyacetic acid [N- (2-oxoperhydro-3-furyl) anilide]. 20. Acetoxyacetic acid [3-bromo-N- (2-oxoperhydro-3-furyl) anilide]. 21. Acetoxyacetic acid [2,3-dimethyl-N- (2-oxoperhydro-3-furyl) anilide]. 22. Acetoxyacetic acid [3-fluoro-N- (2-oxoperhydro-3-furyl) anilide]. 23. Axetoxyacetic acid [2,6-dimethyl-N- (5-methyl-2-oxoperhydro-3-furyl) anilide]. 24. Acetoxyacetic acid [2-methyl-N- (2-oxoperhydro-3-furyl) anilide]. 25. Acetoxyacetic acid [3-chloro-N- (2-oxoperhydro-3-furyl) anilide]. 26. Acetoxyacetic acid [3-cyano-N- (2-oxoperhydro-3-furyl) anilide]. 27. Phenylthio-acetic acid [2,6-dimethyl-N- (2-oxoperhydro-3-furyl) anilide]. 28. Ethylthio-acetic acid [2,6-dimethyl-N- (2-oxoperhydro-3-furyl) anilide]. 29. Isopropylthio-acetic acid [2,6-dimethyl-N- (2-oxoperhydro-3-furyl) anilide]. 30. tert-Buthylthio-acetic acid [2,6-dimethyl-N- (oxoperhydro-3-furyl) anilide]. 31. S- [3-chloro-N- (2-oxoperhydro-3-furyl) anilino-carbonylmethyl] thiuronium chloride. 32. Dimethyldithiocarbamic acid [3-chloro-N- (2-oxoperhydro-3-furyl) anilino-carbonylmethyl] ester. 33. Dimethylthiocarbamic acid [3-fluoro-N- (2-oxoperhydro-3-furyl) anilinocarbonylmethyl] ester. 34. (3-Methylphenylthio) -3-acetic acid [2,6-dimethyl-N- (2-oxoperhydro-3-furyl) anilide]. 35. (Benzylthio) acetic acid [2,6-dimethyl-N- (2-oxoperhydro-3-furyl) anilide]. 36. (2-Aminophenylthio) acetic acid [2,6-dimethyl-N- (2-oxoperhydro-3-furyl) anilide]. 37. Chloroacetoxyacetic acid [2,6-dimethyl-N- (2-oxoperhydro-3-furyl) anilide]. 38. Phenoxyacetic acid [2,6-dimethyl-N- (2-oxoperhydro-3-furyl) anilide]. 39. Chloroacetoxyacetic acid [N- (2-oxoperhydro-3-furyl) anilide]. 40. Chloroacetoxyacetic acid [3-methyl-N- (2-oxoperhydro-3-furyl) anilide]. 41. Chloroacetoxyacetic acid [3-bromo-N- (2-oxoperhydro-3-furyl) anilide]. 42. Phenoxyacetic acid [3-bromo-N- (2-oxoperhydro-3-furyl) anilide]. 43. Phenoxyacetic acid [N- (2-oxoperhydro-3-furyl) anilide]. 44. Phenoxyacetic acid [2,3-dimethyl-N- (2-oxoperhydro-3-furyl) anilide]. 45. Phenoxyacetic acid [3-methyl-N- (2-oxoperhydro-3-furyl) anilide]. 46. Phenoxyacetic acid [2-methyl-N- (2-oxoperhydro-3-furyl) anilide]. 47. Phenoxyacetic acid [3-chloro-N- (2-oxoperhydro-3-furyl) anilide]. 48. Chloroacetoxyacetic acid [3-chloro-N- (2-oxoperhydro-3-furyl) anilide]. 49. Phenoxyacetic acid [2,6-dimethyl-N- (5-methyl-2-oxoperhydro-3-furyl) anilide]. 50. Chloroacetoxyacetic acid [2,6-dimethyl-N- (5-methyl-2-oxoperhydro-3-furyl) anilide]. 51. S- [2,6-dimethyl-N- (2-oxoperhydro-3-furyl) anilinocarbonylmethyl] thiuronium chloride. 52. Isopropylsulfonyl-acetic acid [2,6-dimethyl-N- (2-oxoperhydro-3-furyl) anilide]. 53. A process for the preparation of new acetic anilides according to claims 1 to 52, characterized in that compounds of the general formula II with acid halides of the general formula Hal - CO - CH [deep] 2 - X - R [deep] 3 III optionally dissolved in an organic solvent in the presence of an acid acceptor and the process products are isolated in a manner known per se, where R [deep] 1, R [deep] 2, R [deep] 3 and X have the meaning given above and Hal represents a halogen atom, preferably a chlorine atom. 54. The method according to claim 53, characterized in that in the case that X is sulfur, compounds of the general formula II initially with acid halides of the general formula Hal - CO - CH [deep] 2 - Hal IV optionally dissolved in an organic solvent in the presence of an acid acceptor to give compounds of the general formula V are implemented, which you then with compounds of the general formula or with thiourea of the formula reacted in an inert organic solvent under nitrogen to give the desired process products, where R [deep] 1, R [deep] 2 and R [deep] 3 have the meaning given above, B is an alkali metal atom, preferably sodium, and Hal is a halogen atom, preferably Chlorine. 55. The method according to claim 53, characterized in that in the case that X denotes the sulfinyl or sulfonyl group, compounds of the general formula I. in which R [deep] 1, R [deep] 2 and R [deep] 3 have the meaning given above and X is sulfur, reacted in a solvent with oxidizing agents. 56. Fungicidal agent, characterized by a content of at least one compound according to Claims 1 to 52. 57. Fungicidal agent according to claim 56 as a mixture with carriers and / or auxiliaries. 58. Fungicidal agent characterized by a content of acetic anilides produced by the process according to claims 53, 54 and 55.