HU184201B - Fungicide compositions containing anilides of cyclopropane-carboxylic acid and process for producing these compounds - Google Patents

Abstract

The present invention relates to fungicidal compositions containing as active ingredient at least one Cyclopropancarbonsaureanilid the general formula (I) in addition to carriers or excipients. The compositions according to the invention are surprisingly superimposed on known agents of the same mode of action in the action against phytopathogenic fungi and are additionally distinguished by good plant tolerance and a sufficient duration of action. - Formula I

Description

FIELD OF THE INVENTION The present invention relates to fungicides containing cyclopropanecarboxylic acid anilides against phytopathogenic fungi and to processes for the preparation of novel cyclopropanecarboxylic acid anilides.

Agents acting against phytopathogenic fungi are already known. Such formulations known in the art include, for example, 5-ethoxy-3-trichloromethyl-1,2,4-thiadiazole (U.S. Pat. Nos. 3,260,588 and 3,260,725) or tetramethylthiuram disulfide (642,532). German Patent Specification No. 4,198,198. However, these agents do not always show satisfactory activity against phytopathogenic fungi.

Our task was to develop an excellent agent against phytopathogenic fungi.

The object of the present invention is solved by an agent characterized in that it contains at least one compound of the formula I, wherein

R 1 is hydrogen or C 1-4 alkyl,

R ₂ is phenyl, mono- or polysubstituted, mono- or polysubstituted by C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, halogen, trifluoromethyl and / or cyano, and n is 1 or 2 .

Surprisingly, the compositions of the present invention containing compounds of the formula I have surprisingly superior activity against known phytopathogenic fungi, and the compositions according to the invention are well tolerated by plants and have a satisfactory duration of action. In addition, since they do not have a phytotoxic effect at practical application rates, they are advantageously used in agriculture and horticulture to control phytopathogenic fungi.

The compositions of the invention have excellent fungicidal properties against harmful fungi such as downy mildew.

Known prophylactic fungicides such as N-trichloromethylthiophthalimide (U.S. Patent Nos. 2,553,770, 2,553,771 and 2,553,776) and manganese ethylene bis-dithiocarbamate In contrast to the compositions containing U.S. Patent Nos. 2,504,404 and 2,710,822, the compositions of the present invention containing cyclopropanecarboxylic acid anilides surprisingly have the advantage of being curative and systemic in nature, and are therefore useful in plants. they can also be used against infiltrating pathogens.

The compositions according to the invention are particularly distinguished by their excellent fungicidal activity, which comprises a compound of formula I wherein

R [is hydrogen, methyl or ethyl,

R ₂ represents a phenyl group, methylphenyl group, dimethylphenyl group, ethyl group, isopropyl group, methoxy group, ethoxy group, methylthio group, fluorophenyl , chlorophenyl, bromophenyl, dichlorophenyl, trifluoromethylphenyl or cyanophenyl.

The novel fungicidal compositions of the present invention are compositions, such as powders, sprays, granules, solutions, emulsions or suspensions, containing one or at least two structurally different active compounds of the formula I, liquid and / or solid carriers or diluents.

The novel fungicides may, if desired, contain other fungicides, nematocides, herbicides or a pesticide for the intended purpose.

The fungicidal agents of the invention may optionally contain wetting, tackifying, emulsifying and / or dispersing agents.

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

Solid carriers include, for example, lime, kaolin, chalk, talc, attaclay, and other materials, as well as natural or artificial silica.

Examples of surfactants include salts of lignin sulfonic acid, salts of alkylated benzenesulfonic acids, sulfonated acid amides and their salts, polyethoxylated amines and alcohols.

Dyestuffs may also be mixed with the fungicidal compositions of the present invention for seed dressing in order to impart a clearly visible level to the dressed seed.

The amount of active ingredient or agents in the fungicidal agent according to the invention may vary within wide limits, the exact concentration of the active ingredient depending mainly on the amount of agent used, inter alia, for treating soil or seed or for spraying leaves. For example, the compositions of the present invention may have a concentration of ca. They contain from 1 to 80% by weight, preferably from 20 to 50% by weight, of the active ingredient and from about 99 to 20% by weight of a liquid or solid carrier and optionally up to 20% by weight of surfactant.

For example, the novel compounds of formula 1 may be prepared by reacting a compound of formula II wherein R 1, R ₂ and n are as defined above with a cyclopropanecarboxylic acid chloride III in the presence of an acid acceptor and optionally in the presence of a solvent, preferably in equimolar amounts. and isolating the product of the process in a manner known per se.

Examples of acid acceptors include organic bases such as pyridine, triethylamine or Ν, Ν-dimethylaniline, or inorganic bases such as hydroxides, oxides and carbonates of alkaline earth metals such as sodium, potassium or calcium.

Optional solvents include ether, tetrahydrofuran, benzene, ethyl acetate and the like. Liquid acid receptors, such as pyridine, may be used simultaneously as a solvent.

The reaction is conveniently carried out at a temperature of -10 to + 120 ° C.

The following examples further illustrate the preparation of the compounds of the present invention.

Example 1

Cyclopropanecarboxylic acid [N- (2-oxo-perhydro-3-furyl) anilide] (Compound 1)

Of a solution of 10.62 g (0.06 mole) of 3-anilino-perhydrofuranone-2 in 50 ml of pyridine at an internal temperature of 5-10 ° C.

At 184,201, 6.30 g (0.06 mol) of cyclopropanecarboxylic acid chloride were added dropwise with stirring. After stirring for a further 1/2 hour, it is poured into 200 g of water / ice and mixed well. The product obtained is filtered off with water

Compound sign

denomination

Physical constant melting point, ° C

wash thoroughly and dry in the oven. Yield: 10.25 g = 70% of theory. Melting point: 104 ° C. The following invention may be prepared analogously 5 17th Cyclopropanecarboxylic acid [3- trifluoromethyl-N- (2-oxo-per- hydro-3-furyl) -anilide] 104-105 compounds of the formula: 18th Cyclopropanecarboxylic acid [3- 89 10 fluoro-N- (2-oxoperhydro-3- furyl) -anilide] 19th Cyclopropanecarboxylic acid [3- bromo-N- (2-oxoperhydro- 93-94 3-furyl) -anilide] The Description Physical constant melting point, ° C 15 20th Cyclopropanecarboxylic [2,6- diisopropyl-N- (2-oxoperhydro- 215-216 3-furyl) -anilide] Second Cyclopropanecarboxylic acid [2,6- 102-103 21st cyclopropanecarboxylic 103 diethyl-N- (2-oxoperhydro- 20 [2-ethyl-N- (2-oxoperhydro- 3-furyl) -anilide] 3-furyl) -anilide] Third Cyclopropanecarboxylic acid [2- 175-176 22nd Cyclopropanecarboxylic acid [4- 107 methoxy-N- (2-oxoperhydro- ethyl N- (2-oxo-perhydro-3-FU 3-furyl) -anüid] ril) -anilide] 4th Cyclopropanecarboxylic acid [2- 108-109 25 23rd Cyclopropanecarboxylic acid [4- 75 methyl-N- (2-oxoperhydro- methoxy-N- (2-oxoperhydro- 3-furyl) -anilide] 3-furyl) -anUid] 5th Cyclopropanecarboxylic acid [2,6- 114-116 24th Cyclopropanecarboxylic acid [4- 144-145 dimethyl-N- (2-oxoperhydro- bromo-N- (2-oxoperhydro- 3-furyl) -anilide] 30 3-furyl) -anilide] 6th Cyclopropanecarboxylic acid [2,5- 84 25th Cyclopropanecarboxylic acid [4- 138-139 dimethyl-N- (2-oxoperhydro- fluoro-N- (2-oxoperhydro- 3-furyl) -anüid] 3-furyl) -anilide] 7th Cyclopropanecarboxylic acid [3- 109 35 26th Cyclopropanecarboxylic acid [2- 143-145 methyl-N- (2-oxoperhydro-3- ethoxy-N- (2-oxoperhydro- furyl) -anUid] 3-furyl) -anüid] 8th Cyclopropanecarboxylic acid [4- 123 27th Cyclopropanecarboxylic acid [3- 121-124 methyl-N- (2-oxoperhydro- chloro-2-methyl-N- (2-oxo-per- 3-furyl) -anilide] 40 hydro-3-furyl) anilides] 9th Cyclopropanecarboxylic acid [3,4- 99-100 28th Cyclopropanecarboxylic acid [5- 114-116 dimethyl-N- (2-oxoperhydro- chloro-2-methyl-N- (2-oxo-per- 3-furyl) -anüid] hydro-3-furyl) -anilide] 10th Cyclopropanecarboxylic acid [2,3- 153 29th Cyclopropanecarboxylic acid [4- ng: 1.5520 dimethyl-N- (2-oxoperhydro- 45 methoxy-2-methyl-N- (2-oxo 3-furyl) -aniÍid] perhidro-3-furil) -anilides] 11th Cyclopropanecarboxylic acid [2,4- 85-86 30th Cyclopropanecarboxylic acid [4- ng *: 1.479 dimethyl-N- (2-oxoperhydro- ethoxy-N- (2-oxoperhydro-3- 3-furyl) -anilide] 50 furyl) -anilide] 12th Cyclopropanecarboxylic acid [3,5- 103 31st Cyclopropanecarboxylic acid [5- 163-164 dimethyl-N- (2-oxoperhydro- chloro-2-methoxy-N- (2-oxo-per- 3-furyl) -anilide] hydro-3-furyl) -anilide] 13th Cyclopropanecarboxylic acid 119-121 32nd Cyclopropanecarboxylic acid [3- 95-97 [2,4,6-trimethyl-N- (2-oxo 55 chloro-N- (5-methyl-2-oxo-per- perhydro-3-furyl) -anilide] hydro-3-furyl) -anilide] 14th Cyclopropanecarboxylic acid [4- 149-150 33rd Cyclopropanecarboxylic acid [3- 69-70 chloro-N- (2-oxoperhydro-3- ethyl N- (2-oxo-perhydro-3-FU furyl) -anilide] ril) -anilide] 15th Cyclopropanecarboxylic acid (3- 99-100 60 34th Cyclopropanecarboxylic acid [3- 142-143 chloro-N- (2-oxo-perhydro-3 - cyano-N- (2-oxoperhydro-3- furyl) -anilide] furyl) -anilide] 16th Cyclopropanecarboxylic acid [4- 108-110 35th Cyclopropanecarboxylic acid [3- ng: 1.5888 isopropyl-N- (2-oxo-perhidio- thiomethyl-N- (2-oxoperhydro- 3-furyl) -anilide] 65 3-furyl) -anilide]

-3184 201

Compound sign

denomination

Physical constant melting point, ° C

36. Cyclopropanecarboxylic acid [2,3-136-137 dichloro-N- (2-oxo-perhydro-3-furyl) anilide]

37. Cyclopropanecarboxylic acid [3- 95-97 chloro-N- (5-methyl-2-oxo-perhydro-3-furyl) anilide]

The compounds of the present invention are usually almost colorless, odorless crystalline materials which are almost insoluble in water and gasoline, whereas they are highly soluble in polar organic solvents such as acetone, dimethylformamide and dimethylsulfoxide.

The starting materials for the preparation of the compounds of the invention are known per se or may be prepared by methods known per se.

The following examples further illustrate the possible uses of the compositions of the present invention.

Example 2

Critical concentration test

In case of eradication of Pythium ultimum

20% powder formulations were uniformly mixed with highly contaminated soil with Pythium ultimum. The treated soils were placed in 0.5 liter earth clay pots and 20-20 grains of Wunder von Kelvedon peas were sown per dish without waiting time. After 3 weeks of cultivation at 20-24 ° C, the number of healthy pea plants was determined and root-bonitized.

The active compounds, the amounts used and the results obtained are shown in the table below.

The active ingredient used bulk chemicals Concentrations (mg / liter of soil) The healthy number of peas Root boni- serving (1-4) Comparative agent 5-ethoxy-3-trichloromethyl 10 2 1 1,2,4-thiadiazole 20 5 1 40 12 3 I. Control the) 1 1 (3 reps) b) 0 - contaminated soil c) 0 - II. control the) 19 4 (3 reps) b) 18 4 steamed soil c) 18 4

Root Bonitization: 4: White roots without fungal necrosis;

3: white roots, slight fungal necrosis;

2: brown roots, more pronounced fungal necrosis;

1: severe fungal necrosis, roots rot.

Example 3

Sugar beet seed dressing "Dieckmann-Suprapoly" calibrated sugar beet seed 35 was seed dressed with 20% powdered active ingredient formulations. 2 liters of earth (20X20X5 cm) clay pots were filled with normal compost soil (Damping-off) and 100-100 beet seeds were sown. After 18 days of growing at 40-29 ° C in a greenhouse, healthy seedlings were determined.

The active compounds, the amounts used and the results obtained are shown in the table below.

«Ό «F ö F öígíg

The 5 vials used.

active ingredient g

-i) ep-o

Ó t / 3

SJ,

O 2

Cyclopropanecarboxylic acid 10 17 4 [N- (2-oxoperhydro- 20 17 4 3-furyl) -anüid] 40 18 4 Cyclopropanecarboxylic acid 10 16 4 [2,6-Dimethyl-N- (2-oxo- 20 20 4 perhidro-3-furil] -anilides 40 19 4 Cyclopropanecarboxylic acid 10 19 4 [3-Chloro-N- (2-oxo-per- 20 17 4 hydro-3-furyl) -anilide] 40 17 4 Cyclopropanecarboxylic acid 10 10 1 [3-methyl-N- (2-oxo-per- 20 16 2 hydro-3-furyl) anilides] 40 16 4 Cyclopropanecarboxylic acid 10 10 1 [2-methoxy-N- (2-oxo-per- 20 16 2 hydro-3-furyl) anilides] 40 20 4

The active ingredient used agent g / kg seed Number of healthy seedlings Cyclopropanecarboxylic acid [N- (2- 0.4 79 oxoperhydro-3-furyl) -anilide] 0.8 79 1.6 75 Cyclopropanecarboxylic acid [2.6 0.4 70 dimethyl-N- (2-oxoperhydro- 0.8 76 3-furyl) -anilide] 1.6 83 Cyclopropanecarboxylic acid [3- 0.4 83 chloro-N- (2-oxoperhydro- 0.8 82 3-furyl) -anilide] 1.6 93 Cyclopropanecarboxylic acid [3- 0.4 77 methyl-N- (2-oxoperhydro- 0.8 71 3 furyl) anilides] 1.6 85 Cyclopropanecarboxylic acid [2- 0.4 83 methoxy-N- (2-oxoperhydro · 0.8 87 3-furyl) -anilide] 1.6 87

184,201

Agents used ^Harom óanyag healthy seedlings active seed sama comparator:

5-ethoxy-3-trichloromethyl 0.4 26 1,2,4-thiadiazole 0.8 44 1.6 53 Tetramethylthiuram disulfide 4.8 21 9.6 50 I. Control the) 5 (3 reps) b) 7 contaminated soil c) 6 II. control the) 83 (3 reps) b) 86 steamed soil c) 81

Example 4

The effect of preventive leaf treatment against Plasmopara viticola on cuttings in a greenhouse

Young cotyledons with about 5 to 8 leaves were sprayed completely in water with the formulation containing the following concentrations, and after the spray coating had dried, the back of the leaves was sprayed with an aqueous suspension of fungal sporangia (about 20,000 sprangium / ml) and It was immediately incubated at C and preferably in a water-saturated atmosphere. From Day 2, humidity was reduced to normal (about 30-70% saturation) for 3 to 4 days, and a saturated water vapor atmosphere was provided for another day. The percentage of fungal infested surface of each leaf was then recorded and the average fungicide treatment was calculated as follows:

100 * infestation of treated plants infestation of untreated plants% effect = 100 -

The active ingredient used % effect against Plasmopara viticola * Concentration of active substance 45 Cyclopropanecarboxylic acid [2,6-diethyl N- (2-oxo-perhydro-3-furyl) anilide] 40 0,025 50 Cyclopropanecarboxylic acid [3-fluoro-N- (2-oxo-perhydro-3-furyl) -anilide] 100 0,025 Cyclopropanecarboxylic acid [3-bromo-N- (2-oxo-perhydro-3-furyl) -anilide] 100 0,025 55 Cyclopropanecarboxylic acid [2,6-di- isopropyl-N- (2-oxoperhydro- 3-furyl) -anilide] 84 0,025 Cyclopropanecarboxylic acid [2-ethyl-N- (2-oxo-perhydro-3-furyl) -anilide] 83 0,025 60 Cyclopropanecarboxylic acid [4-ethyl-N- (2-oxo-perhydro-3-furyl) -anilide] 40 0,025 Cyclopropanecarboxylic acid [4-fluoro-N- (2-oxo-perhydro-3-furyl) -anilide] 100 0,025 65

* c Λ * 37 » ooo; o The active ingredient used '5 g, «2 o ^{Λ after} > » 'Λ '§ 5 9 c. She Cyclopropanecarboxylic acid [2-ethoxy-N- (2-oxo-perhydro-3-furyl) anilide] 70 0,025 Cyclopropanecarboxylic acid [3-chloro 2-methyl-N- (2-oxoperhydro-3-furyl) - anilide] 98 0,025 Cyclopropanecarboxylic acid [3-ethyl-N- (2-oxo perhydro-3-furyl) anilide] 100 0,025 Cyclopropanecarboxylic acid [3-cyano-N- (2-oxo perhydro-3-furyl) anilide] 100 0,025 Cyclopropanecarboxylic acid [3-thiomethyl-N- (2-oxo-perhydro-3-furyl) -anilide] 70 0,025 Cyclopropanecarboxylic acid [2,3-dichloro-N- (2-oxo-perhydro-3-furyl) -anilide] 100 0,025 Cyclopropanecarboxylic acid [N- (2-oxoperhydro-3-furyl) anilides] 100 0,001 Cyclopropanecarboxylic acid [3-chloro-N- (2-oxo perhydro-3-furyl) anilide] 100 0,001

* the effect was compared to 100% infection of the untreated control.

Example 5

Effect of preventive leaf treatment against Phytophthora infestans on tomato plants or potato plants in greenhouses

Young tomato plants with at least 2 developed foliage leaves or potato plants at least 10 cm high (for example, potato plants grown from bud cuttings) were completely sprayed with water with a formulation containing the specified concentration of active ingredient and sprayed with incubated in a refrigerator for about 2 hours at 11 ° C. Plants with high humidity and more. After incubation at 15-18 ° C in a greenhouse, the percentage of infected leaf areas was determined after about 5 days. The fungicidal effect was calculated as follows: 100 · Infection of the treated plants o f water 1% Infectivity _of untreated plants against Phytophthora infestans in potato *:

The active ingredient used

Drug Concentration

0.005%

Cyclopropanecarboxylic acid [N- (2-oxo-per-95-hydro-3-furyl) anilide]

Cyclopropanecarboxylic acid [2,6-dimethyl-80];

N - (2-cxo-perhydro-3-furyl) anilides]

184,201

The active ingredient used bulk chemicals concentration 0.005% Reference substance: manganese ethylene bis-dithiocarbamate 50 % effect against Phytophthora infestans in tomato * The active ingredient used bulk chemicals concentration 0.005% Cyclopropanecarboxylic acid [N- (2-oxoperhydro-3-furyl) -anilide] 100 Cyclopropanecarboxylic acid [3-methyl-N- (2-oxo-perhydro-3-furyl) -anilide 81 Cyclopropanecarboxylic acid [3-chloro-N- (2-oxoperhydro-3-furyl) -anilide] 91 comparator: manganese ethylene bis-dithiocarbamate 67

* The effect was compared to 100% infection of the untreated control.

Example 6

Systemic effect of soil treatment against Phytophthora infestans on tomato plants in greenhouses

Flaxseed formulations were mixed with soil (weight / volume), potted and seeded with at least 2 mature leafy tomato plants or at least 10 cm tall potato plants (e.g., potato plants developed from bud cuttings). After the desired waiting time (e.g. 4 or 18 days), the plants were sprayed with an aqueous suspension of the fungus containing 50,000 to 80,000 sporangia per ml and incubated in a refrigerator for about 2 hours at 11 ° C. The plants were incubated at high humidity and at about 15-18 ° C in a greenhouse and grown for about 1 hour. After 5 days, the percentage of infected leaf surfaces was determined. The fungicidal effect was calculated as follows:

_m ,, ___% infection of treated plants = 100 ---— τ-τ -—- r- _f -—— infection of untreated plants

Systemic effect of soil treatment against Phytophthora infestans on tomato plants * day 18 day ppm -——.

The active ingredient of the agent is _the effect of treatment with the substance prior _to modulation

Cyclopropanecarbon-25 89 85 acid [N- (2-oxo-perhydro-570 89)

3-furyl) -anüid]

Active ingredient ppm active material 4 days 18 days effect of pre-inoculation treatment Ciklopropánkarbon- 25 92 82 acid [2,6-dimethyl-N- (2- oxoperhydro-3-furyl) - anilide] 5 40 71 * The effect was compared to untreated. control 100% infection-

Example 7

Healing effect of leaf treatment against Phytophthora infestans on tomato plants in greenhouses

Young tomato plants with at least 2 mature foliage leaves or potato plants at least 10 cm high (e.g., potato sprouts) were sprayed with an aqueous suspension of the fungus containing 50,000 to 80,000 sporangia per milliliter and kept in a refrigerator at about 11 ° C for 2 hours. Plants were incubated at high humidity. After the desired waiting time, the plants were sprayed completely in water with the fungicidal composition of the concentration to be tested during the latent period of fungal infection. After emergence of fungal infestation on untreated control plants, the percentage of infected leaf areas was determined. The fungicidal effect was calculated as follows:

"" "Infection rate of treated plants% effect = 100 ---—-— day infection of untreated plants

Sprayed inoculation the active substance in the active agent before inoculation material used, perhaps _u effect% Treatment

Cyclopropanecarboxylic acid [N- (2-oxo-perhydro-3-furyl) anilide] 0,004 100 68 Cyclopropanecarboxylic acid [2,6-dimethyl-N- (2-oxo-perhydro-3-furyl) -anilide] comparator: 0,004 100 60 manganese-ethylene-bis dithiocarbamate 0,004 Example 8 91 0 Barley seeds Helminthosporium spec. treatment

Barley seeds infected with Helminthosporium spec. Were treated with the composition of the present invention so that 50 mg of active ingredient per 100 g of seed was obtained. The seeds were then seeded and incubated in an air conditioner at + 15 ° C. The experiment

Assessed after 184 201 weeks; treated seedlings were much less infected than untreated control plants.

The active ingredient used is a% effect

Cyclopropanecarboxylic acid [4-methyl-N- (2-oxo-40 perhydro-3-furyl) anilide]

Cyclopropanecarboxylic acid [2,4-dimethyl-N- (2-40 oxo-perhydro-3-furyl) -anilide]

Cyclopropanecarboxylic acid [4-ethyl-N- (2-oxo-40 perhydro-3-furyl) anilide]

Untreated control 0

Example 9

Boundary Concentration Assay In the case of Pythium ultimum eradication,% powder formulations were uniformly mixed with highly contaminated soil with Pythium ultimum. The treated soils were placed in 0.5 liter earth clay pots and, without waiting time, 20 to 20 grains of Pisum sativum L. convar. Medullare Alef. After 3 weeks of cultivation at 20-24 ° C, the number of healthy pea plants was determined and root-bonitized.

The nutrients, amounts used and results are shown in the table below.

Root Bonitization: 4: White roots without fungal necrosis;

3: white roots, slight fungal necrosis;

2: brown roots, more pronounced fungal necrosis;

1: severe fungal necrosis, roots rot.

The active ingredient used Concentration of active substance (mg / ml soil Number of healthy peas Root- bonitation (1-4) Ciklopropánkarbon- 20 18 4 acid [3-fluoro-N- (2-oxo - 40 20 4 perhydro-3-furyl) - anilide] 80 19 4 Ciklopropánkarbon- 20 17 4 acid [3-bromo-N- (2-oxc »- 40 19 4 perhydro-3-furyl) - anilide] 80 20 4 Ciklopropánkarbon- 20 18 4 acid [4-fluoro-N- (2-oxo - 40 19 4 perhydro-3-furyl) - anilidj 80 18 4 Ciklopropánkarbon- 20 7 2 acid [2-ethoxy-N- (2-oxo .- 40 17 2 perhydro-3-furyl) - anilino] 80 19 4

Active ingredientThe active ingredient of the concentrate used is cation (mg / ml Number of healthy peas Root- bonitation (1-4) soil Ciklopropánkarbon- 20 15 1 acid [3-chloro-N- (5-methyl- 40 19 4 2-oxo perhydro-3-furyl) anilides] 80 19 4 Ciklopropánkarbon- 20 20 4 acid [3-cyano-N- (2-oxo- 40 18 4 perhydro-3-furyl) - anilide] 80 18 4 Ciklopropánkarbon- 20 - - acid [2,3-dichloro-N- (2- 40 10 3 oxoperhydro-3-furyl) - anilide] comparator: 80 11 3 manganese-ethylene-1,2- 20 3 1 bis (dithiocarbamate) 40 8 1 80 10 1 I. Control the) 1 1 (3 reps) b) 0 1 contaminated soil c) 0 1 II. control the) 19 4 (3 reps) b) 17 4 fumes soil c) 18 4

Example 10

(a) 80% by weight of N-2- (oxo-perhydro-3-furyl) -anilide cyclopropanecarboxylic acid% by weight of calcium salt of lignin sulphonic acid% by weight of ammonium salt of tetraethylene glycol nonylphenyl ether mono-sulfonic acid colloidal silica

b) 20% by weight of cyclopropanecarboxylic acid N- (2-oxo-perhydro-3-furyl) -anilide 70% by weight tonsil% by weight cell resin weight% fatty acid condensation product based wetting agent

c) 10% by weight of cyclopropanecarboxylic acid N- (2-oxo-perhydro-3-furyl) -anilide 60% by weight of clay mineral 15% by weight of silica 10% by weight of cellulose based on the N-methyl-N-alkyl tauride sodium salt and the calcium salt of lignin sulphonic acid surfactants

Claims (23)

CLAIMS 1. A fungicidal agent, wherein the active ingredient is a cyclopropanecarboxylic acid anilide of the formula I in an amount of from 10 to 80% by weight. R 1 is hydrogen or C 1-4 alkyl, R ₂ is phenyl or C 1-4 alkyl, C 1-4 alkoxy, C 1-4 alkylthio, halogen, Phenyl, singly or multiply substituted, mono- or polysubstituted, with trifluoromethyl and / or cyano, and n being 1 or 2, containing one or more conventional carriers or diluents, preferably mineral and / or surfactant, preferably fatty acid methyl - Tauride, calcium salt of lignin sulphonic acid, alkylphenol polyglycololether and fatty acid condensation product -. 2. An agent according to claim 1 wherein the active ingredient is cyclopropanecarboxylic acid [N- (2-oxo-perhydro-3-furyl) anilide]. An agent according to claim 1, wherein the active ingredient is cyclopropanecarboxylic acid [2,6-diethyl-N- (2-oxo-perhydro-3-furyl) anilide]. 4. An agent according to claim 1 wherein the active ingredient is cyclopropanecarboxylic acid [2-methoxy-N- (2-oxo-perhydro-3-furyl) anilide]. 5. An agent according to claim 1, wherein the active ingredient is cyclopropanecarboxylic acid [2,6-dimethyl-N- (2-oxo-perhydro-3-furyl) anilide]. 6. An agent according to claim 1 wherein the active ingredient is cyclopropanecarboxylic acid [3-methyl-N- (2-oxo-perhydro-3-furyl) anilide]. 7. An agent according to claim 1 wherein the active ingredient is cyclopropanecarboxylic acid [4-methyl-N- (2-oxo-perhydro-3-furyl) anilide]. 8. The agent of claim 1 wherein the active ingredient is cyclopropanecarboxylic acid [2,4-dimethyl-N- (2-oxo-perhydro-3-furyl) anilide]. 9. An agent according to claim 1 wherein the active ingredient is cyclopropanecarboxylic acid [3-chloro-N- (2-oxo-perhydro-3-furyl) anilide]. 10. The agent of claim 1 wherein the active ingredient is cyclopropanecarboxylic acid [3-fluoro-N- (2-oxo-perhydro-3-furyl) anilide]. 11. The agent of claim 1 wherein the active ingredient is cyclopropanecarboxylic acid [3-bromo-N- (2-oxo-perhydro-3-furyl) anilide]. 12. The agent of claim 1 wherein the active ingredient is cyclopropanecarboxylic acid [2,6-diisopropyl-N- (2-oxo-perhydro-3-furyl) anilide]. 13. The agent of claim 1 wherein the active ingredient is cyclopropanecarboxylic acid [2-ethyl-N- (2-oxo-perhydro-3-furyl) anilide]. 14. An agent according to claim 1, wherein the active ingredient is cyclopropanecarboxylic acid [4-ethyl-N- (3-oxo-perhydro-3-furyl) anilide]. 15. An agent according to claim 1, wherein the active ingredient is cyclopropanecarboxylic acid [4-fluoro-N- (2-oxo-perhydro-3-furyl) anilide]. 16. The agent of claim 1, wherein the active ingredient is cyclopropanecarboxylic acid [2-ethoxy-N- (2-oxo-perhydro-3-furyl) anilide]. 17. The agent according to embodiment of Claim 1 wherein said compound is cyclopropanecarboxylic acid [3-chloro-2-methyl-N- (2-oxoperhydro-3-furyl) -anilide] ¹⁰ talmaz cent tar. 16. An agent according to claim 1 wherein the active ingredient is cyclopropanecarboxylic acid [3-chloro-N- (5-methyl-2-oxo-perhydro-3-furyl) anilide]. 1R 19. The agent of claim 1 wherein the active ingredient is cildopropanecarboxylic acid [3-ethyl-N- (2-oxo-perhydro-3-fur]) -anilide. 20. The agent of claim 1 wherein the active ingredient is cyclopropanecarboxylic acid (3-cyano-N- (2-oxo-perhydro-3-furyl) anilide). 21. The agent of claim 1, wherein the active ingredient is a glaze containing cyclopropanecarboxylic acid [3-thiomethyl-N- (2-oxo-perhydro-3-furyl) anilide]. 22. The agent of claim 1, wherein the active ingredient is cyclopropanecarboxylic acid [2,3-dichloro-N- (2-oxo-perhydro-3-furyl) anilide]. 30 23. An agent according to claim 1, wherein the active ingredient is cyclopropanecarboxylic acid (3-chloro-N- (5-methyl-2-oxo-perhydro-3-furyl) -anil). 24. A process for preparing the cyclopropane 35 carboxylic acid anilides of formula (I) R 1 is hydrogen or C 1-4 alkyl, R ₂ is phenyl or C 1-4 alkyl, C 1-4 alkoxy, 1-4 Mono- or polysubstituted, singly or multiply identical or differently substituted with C 40 t alk alkylthio, halogen, trifluoromethyl and / or cyano, and n is 1 or 2 45, characterized in that a compound of formula II wherein R,, R R ₂ and n are as defined above, with an cyclopropanecarboxylic acid chloride of formula (III) in the presence of an acid acceptor and optionally in the presence of a solvent, preferably equimolar amounts. The reaction product is reacted in 50 ratios and the product of the process is isolated in a manner known per se.