HU180985B - Fungicide compositions containing anilide derivatives of furane-carbocylic acid - Google Patents

Abstract

The present invention provides fungicidally active furancarboxylic acid anilides of the general formula I <IMG> (I) in which R1 represents a hydrogen atom or an alkyl group containing 1 to 4 carbon atoms, R2 represents an unsubstituted phenyl group or a phenyl group substituted by one or more substituents selected from alkyl groups containing 1 to 4 carbon atoms, alkoxy groups containing 1 to 4 carbon atoms, alkylthio groups containing 1 to 4 carbon atoms, halogen atoms, trifluoromethyl groups, nitro groups, alkoxycarbonyl groups containing 1 to 4 carbon atoms in the alkoxy parts, alkylcarbonyl groups containing 1 to 4 carbon atoms in the alkyl parts, phenyl and cyano groups, and ?n represents 1 or 2. When the substituted aromatic hydrocarbon group represented by R2 contains two or more substituents these substituents may be the same or different.

Description

Fungicides containing furan carboxylic acid anilides

FIELD OF THE INVENTION This invention relates to fungicidal compositions containing furan carboxylic anilide derivatives.

Preparations which act on phytopathogenic fungi are already known. In practice, such formulations contain, for example, the active ingredient 5-ethoxy-3-trichloromethyl-1,2,4-thiadiazole (U.S. Pat. Nos. 3,260,725 and 3,260,588) or tetramethylthiuran disulfide (Federal Republic of Germany, 642,532). . However, these preparations do not always have a satisfactory effect on fungi on leaves and soil.

It is an object of the present invention to provide a composition which exhibits improved activity against fungi on leaves and soil compared to known compositions.

It has been found that this object can be achieved by the use of an agent comprising at least one compound of formula I as an active ingredient, wherein

R1 represents a hydrogen atom or a C1-C4 alkyl group,

R _{2 represents} phenyl or phenyl substituted by one or two C 1 -C 4 alkyl or halogen atoms.

Surprisingly, it has been found that the compositions of the compounds of the formula I have an activity against fungi in leaves and soil that are known to have the same effect, and that the compositions according to the invention are well tolerated by plants and have an effective action. In addition, the amounts used in practical application are non-phytotoxic, so that these compositions are advantageous for use in agriculture and horticulture to control fungi on plants and soil.

Formulations containing compounds of formula I exhibit excellent fungicidal properties against harmful fungi.

In contrast to known prophylactic fungicides, which contain, for example, N-trichloromethylthiophthalimide (U.S. Patent 2,553,770) and 5 manganese ethylenebisdithiocarbamates (U.S. Patent No. 2,504,404) as the active ingredient, they even have a healing and systemic effect and can be used to control pathogens that have already penetrated the plants.

The compositions of the invention are excellent fungicides their effectiveness are distinguished especially by incorporating the compound of Formula I as an active ingredient of the formula wherein R hidro5 hydrogen; and, is ethyl or methyl and R ₂ phenylll-, methylphenyl, dimethylphenyl, etilfenü-, izopropüfenil-, fluorophenyl , chlorophenyl or bromophenyl.

The novel fungicidal compositions of the present invention, such as powders, sprays, gra180985

-1180985 zero solutions, solutions, emulsions or suspensions, containing as active ingredient one or at least two compounds of the formula I in liquid and / or solid carriers or diluents.

The new fungicides may optionally contain other substances suitable for the intended purpose, such as other fungicides, nematocides, herbicides or other pesticides.

For example, enhancers such as organic solvents, wetting agents and oils may be added to enhance the effect and rate of action of the agents of the present invention. The use of such additives makes it possible to reduce the amount of the actual active ingredient to be used.

In addition to the above, the agents of the invention may optionally contain other surfactant additives, e.g. they may also contain adjuvants, emulsifiers and / or dispersants.

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

Solid carriers include limestone, kaolin, chalk, talc, diatomaceous earth and other clays as well as natural and synthetic 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.

If the compositions are used for seed dressing, coloring agents may also be added to give the seed dressing a clearly visible color.

The proportions of the active ingredient (s) in the various formulations may be varied within wide limits, the exact concentration of the active ingredient employed being dependent mainly on the amount of the composition to be applied to the soil or seed treatment or to the treatment of the above-ground plant parts. For example, the compositions may contain from about 1% to about 80% by weight of the active ingredient, preferably from about 20% to about 50% by weight of the active ingredient, and from about 99% to about 20% by weight of the liquid or solid carrier.

For example, the compounds of Formula I may be prepared by reacting a compound of Formula II, wherein R 1, R _2, and n in the presence of an acid acceptor and optionally a solvent, with furan carboxylic acid chloride, and isolating the product 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 alkali and alkaline earth metals such as sodium, potassium or calcium hydroxide, oxide and carbonate.

Suitable solvents are, for example, ethers, 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 ° C to 120 ° C.

The following examples illustrate the process.

Example 1

Furan-2-carboxylic acid [N- (2-oxo-operhydro-3-furyl) -2,6-dimethylanilide]

To a solution of 3- (2,6-dimethylanilino) perhydrofuran-2-one (300 g, 1.46 mol) in dry pyridine (600 ml) was added dropwise furan-2-carboxylic acid chloride (206.2 g, 1.58 mol) at room temperature. After the addition is complete, the pyridine complex precipitates with increasing temperature. The reaction mixture was further stirred for 3 hours. The reaction mixture was heated at 50 ° C and then concentrated in vacuo to half its volume. It is then poured into 2.5 L of ice-cold 5% hydrochloric acid with stirring and filtered after 30 minutes. Rinse well with water and dry under vacuum at 70 ° C.

Yield: 387 g (89%), m.p. 135-138 ° C.

Example 2

Furan-2-carboxylic acid [2-chloro-N- (2-oxoperhydro-3-furyl) -anilide]

3- (2-Chloroanilino) -perhydrofuran-2-one (21.16 g, 0.1 mol) was stirred at room temperature with 13.05 g (0.1 mol) of furan-2-carboxylic acid chloride. The reaction mixture was slowly heated to 120 ° C and held at this temperature for 1.5 hours until the evolution of hydrochloric acid was complete. After cooling to ^r eakció_elegy.iez 100 ml of ethyl acetate and washed with saturated sodium bicarbonate solution until neutral. The ethyl acetate layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The residual oil was crystallized with a small amount of ether, then filtered and the crystals washed with diisopropyl ether.

Yield: 21.4 g (70%), m.p. 98-100 ° C.

Example 3

Furan-2-carboxylic acid [N- (2-oxoperhydro-3-furyl) -anilide]

A solution of 3-anilinoperhydrofuran-2-one (14.16 g, 0.08 md) in ethyl acetate (150 mL) was stirred with a solution of sodium carbonate (9.54 g, 0.09 mol) in water (15 mL). 11.70 g (0.09 mol) of furan-2-carboxylic acid chloride were then added dropwise under ice-cooling. After stirring for 1 hour, the reaction mixture is optionally neutralized with a small amount of sodium carbonate solution and extracted with ethyl acetate. After drying over magnesium sulfate, the ethyl acetate solution was evaporated to dryness in vacuo and the solid residue was stirred with a small amount of ether-ethanol. It is filtered, washed with ether and recrystallized from ethanol.

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Yield: 10.6 g (49%), m.p. 140-141 ° C. Name of compound Melting point í ° \ Similarly, it can be prepared the following- b. 5 Furan-2-carboxylic acid [4-fluoro-N- (2- -oxoperhidro-3-furyl) -anilide] 165-166 Name of compound melting point CO Furan-2-carboxylic acid [2,5-dimethyl-N- - (2-oxoperhydro-3-furyl) -anilide] 120-121 Furan-2-carboxylic acid [2,6-diethyl-N- (2-oxoperhydro-3-furyl) -anilide] 124-125 10 Furan-2-carboxylic acid [2,6-diisopropyl- N- (2-oxoperhydro-3-furyl) -anilide] 149-150 Furan-2-carboxylic acid [2-ethyl-6-methyl-N- (2-oxoperhydro-3-furyl) -anilide] 127-129 Furan-2-carboxylic acid [3,5-dichloro-N- (2-oxo-rhydro-3-furyl) -anil] 143-145 Furan-2-carboxylic acid [2,6-dimethyl-N- (5-methyl-2-oxoperhydro-3-furyl) - 15 Furan-2-carboxylic acid [3-chloro-2-methyl- anilide] 190-191 -N - (2-oxoperhydro-3-furyl) anilides] 151 Furan-2-carboxylic acid [3,4-dichloro-N- Furan-2-carboxylic acid [5-chloro-2-methylnicotinamide - (2-oxoperhydro-3-furyl) -anilide] 139-141 20 -N - (- oxoperfido-3-furyl) anilides] 138-139 Furan-2-carboxylic acid [2-methyl-N- (2- Furan-2-carboxylic acid [3-chloro-N- - (2-oxoperhydro-3-furyl) -anilide] 132 - (5-methyl-2-oxoperhydro-3-furyl) anilides] 105-108 Furan-2-carboxylic acid [2,4-dimethyl-N- - (2-oxoperhydro-3-furyl) -anilide] 123-124 25 Furan-2-carboxylic acid [3-fluoro-N- (5-methyl-2-oxoperhydro-3-furyl) - Furan-2-carboxylic acid (3,4-dimethyl-N- • (2-oxoperhydro-3-furyl) -anilide] 122 anilide] 93-94 30 Furan-2-carboxylic acid [2-chloro-6-methyl- Furan-2-carboxylic acid [2,3-dimethyl-N- N- (2-oxoperhydro-3-furyl) -anilide] 145-148 - (2-oxoperhydro-3-furyl) -anilide] 129-130 Furan-2-carboxylic acid [2-bromo-N- Furan-2-carboxylic acid [3,5-dimethyl-N- - (2-oxoperhydro-3-furyl) -anilide] 161-162 35 - (2-oxoperhydro-3-furyl) -anilide] 118 Furan-2-carboxylic acid [2,3-dichloro-N- Furan-2-carboxylic acid (3-methyl-N- - (2-oxoperhydro-3-furyl) -anilidj 121 - (2-oxoperhydro-3-furyl) anilides] 126 Furan-2-carboxylic acid-3-e til-N- Furan-2-carboxylic acid [4-methyl-N- (2- -oxoperhidro-3-furyl) -anilide] 118-119 40 - (2-oxope rhidro-3-furyl) -an il d] 128-129

Furan-2-carboxylic acid [3-chloro-N- (2-oxoperhydro-3-furyl) anilide] 134-135 Furan-2-carboxylic acid [4-chloro-N- (2- -oxoperhidro-3-furyl) -anilide] 157-158 Furan-2-carboxylic acid {2-ethyl-N- (2- -oxoperhidro-3-furyl) -anilide] 122-123 Furan-2-carboxylic acid [4-isopropyl-N '- (2-oxoperhydro-3-furyl) anilide] 95-96 Furan-2-carboxylic acid [3-bromo-N- (2-oxoperhydro-3-furyl) -anilide] 150-153 Furan-2-carboxylic acid [4-ethyl-N- (2- -oxoperhidro-3-furyl) -anilide] 120-121 Furan-2-carboxylic acid [4-bromo-N- (2- -oxoperhidro-3-furyl) -anilide] 137-140 Furan-2-carboxylic acid [3-fluoro-N- (2- -oxoperhidro-3-furyl) -anilide] 142-144

Compounds of formula I are generally almost colorless, odorless crystalline compounds which are almost insoluble in water and gasoline, but very soluble in polar organic solvents such as acetone, dimethylformamide and dimethylsulfoxide.

The compounds used as starting materials are known or can be prepared by known procedures in the method of the present invention _50.

The compositions of the present invention to illustrate the potential use of the following Examples ₅₅ jukmeg.

Example 4 ₆₀ Limit Concentration Assay for Pythium Ultimum Extermination

Powdered formulations containing 20% of the active ingredient were uniformly mixed with Pythium ultimum strongly cooked soils. The ke

-3180985 green soils were filled into 0.5 liter clay pots and 20-20 "Wunder von Kelvedon" seed peas were seeded into each dish without waiting time. After three weeks of incubation at 20-24 ^° C for determining the number of healthy peas tuk plants and root bonitation performed (1-4).

The active compounds, amounts used and results obtained are given in Table ⁵ below.

bulk chemicals Healthy Root The preparation concentration peas bonitation The active (mg / liter of soil) number (1-4)

F uranium 2-carboxylic acid [N- (2-oxoperhydro- 10 mg 10 2 3-furyl) -anilide] 20 mg 14 3 40 mg 15 4 F uranium 2-carboxylic acid [N- (2-oxope rhydro- 10 mg 16 4 3-furyl) -2,6-dimetilanilid] 20 mg 16 4 40 mg 19 4 Furan-2-carboxylic acid [2,6-dimethyl-N- 10 mg Ί 2 - (5-methyl-2-oxoperhydro-3-furyl) -anilidj 20 mg 15 3 40 mg 18 4 Furan-2-carboxylic acid [3-methyl-N- 10 mg 4 1 - (2-oxoperhydro-3-furyl) -anilidJ 20 mg 9 2 40 mg 17 3 Furan-2-carboxylic acid [3-chloro-N- 10 mg 14 3 - (2-oxopeihidro-3-furyl) -anilide] 20 mg 19 4 40 mg 17 4 Furan-2-carboxylic acid [3-bromo-N- 10 mg 10 2 - (2-oxoperhydro-3-furyl) -anilide] 20 mg 15 4 40 mg 14 4 Furan-2-carboxylic acid [3-fluoro-N- 10 mg 10 3 • (2-oxoperhydro-3-furyl) -anilide 20 mg 16 4 40 mg 19 4 Comparative times 5-ethoxy-3-trichloromethyl 10 mg 2 1 -1,2,4-thiadiazole 20 mg 5 1 40 mg 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;

= white roots, slight fungal necrosis;

= brown roots with stronger fungal necrosis;

= severe necrosis, roots rot:

Example 5

Sugar beet seed dressing 60 "Dieckmann-Suprapoly" calibrated sugar beet seeds were seeded with 20% powdered active ingredient formulations. Two compartments (20 x 20 x 5 cm) of clay pots were filled with normal compost soil (Daming-off) and 100-100 beet seeds were sown in each pot. After 18 days at 19-21 ° C in a greenhouse, healthy seedlings were counted.

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

Active ingredient of the preparation Active substance content (g / kg seed) Number of healthy plants hatched from 100 seeds 5 Furan-2-carboxylic acid [N- (2- 0.4 84 -oxope rhidro-3-furyl) - 0.8 90 10 -2,6-dimethyl-anilide] 1.6 91 Furan-2-carboxylic acid [3- 0.4 73 chloro-N- (2-oxoperhidro- 0.8 71 3-furyl) -anilide] 1.6 91 15 Furan-2-carboxylic acid [3- 0.4 75 fluoro-N- (2-oxoperhidro- 0.8 79 3-furyl) -anilide] 1.6 75 Furan-2-carboxylic acid [2,3-di- 0.4 74 20 methyl-N- (2-oxoperhidro- 0.8 82 3-furyl) -anilide] 1.6 85 Furan-2-carboxylic acid [3- 0.4 72 25 methyl-N- (2-oxoperhid- 0.8 78 ro-3-furyl) -anilide] 1.6 79 Furan-2-carboxylic acid [2,6- 0.4 57 -dimethyl-N- (5-methyl-2- 0.8 70 30 -oxope rhidro-3-furyl) · -anilides] 1.6 92 Furan-2-carboxylic acid [3- 0.4 56 bromo-N- (2-oxoperhidro- 0.8 55 35 3-furyl) -anilide] 1.6 75 összehasonlítószer 5-ethoxy-3-triklónnetil- 0.4 26 -1,2,4-thiadiazole 0.8 44 1.6 53 40 Tetrametiltiurám- 4.8 21 disulfide 9.6 50

Active ingredient of the preparation Quantity of active substance (g / kg of seed) Number of healthy plants hatched from 100 seeds I. Control (3 reps) the) 5 Contaminated soil b) 7 c) 6 II. control (3 reps) the) 83 steamed soil b) 86 c) 81 Example 6

Eradication of Pythium splendens in Poinsettia pulcherrima culture

Young, rooted "Annette He® Diva" poinsettia plants were planted in clay pots 11 cm in diameter. The potted substrate (a 1: 1 mixture of peat culture substrate and sandy compost · soil) was heavily infected with Pythium splendens. After planting, the plants were watered once with 100 ml of the specified concentration. The plants were then placed in a greenhouse at 20-21 ° C for 10 weeks. At the end of the cultivation, we measured the height of 10-10 plants, the fresh weight of the leaves and the "Braktee", and performed root-bonitization.

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

Active ingredient of the preparation Active ingredient / concentration % plant height Fresh weight of leaves Fresh weight of "Braktee" Root Bonitale ¹ (1-4) Furan-2-carboxylic acid [N- 0.02 40 cm 13g 16g 4 - (2-oxoperhydro-3-furyl) - 0.04 39 cm 12g 13g 4 -2,6-dimethyl-anilide] 0.08 42 cm 13g H g 4 Furan-2-carboxylic acid [N- 0.02 38 cm 13g 13g 3 - (2-oxoperhydro-3-furyl) - 0.04 37 cm 12g 14g 3 anilide] 0.08 35 cm 13g 15g 3 I. Control Contaminated soil 12 cm 4g 4g 1 II. control Steamed soil 43 cm 17g 15g 3

Root Bonitization: 4 = no infection = low infection = moderate infection = severe infection

Example 7

Control of pests causing onion rot and root rot in tulip shoots Prepared tulip bulbs of the Gander variety have been stripped of their shells and 12-12 bulbs

We planted it in 27x27x 12 cm wooden boxes. The substrate (sandy compost soil) was highly contaminated with Pythium ultimum and Pythium sylvaticum. The worked into the soil before planting balanced ⁵ in detail, the composition as a 10% powder preparation. Cultivation was carried out for 47 days at a slowly rising soil temperature of 12-17 ° C. The cut flowers were weighed, measured induced bulb rot növényvesztesé get ^10, and subjected to root bonitation.

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

Active ingredient of the preparation

Furan-2-carboxylic acid [N- (2-oxoperhydro-3-furyl) -2,6-dimethylanilide]

I. Control

Contaminated soil

II. control

Steamed soil

Concentration of active substance (mg / liter of soil) Average weight of cut flowers Plants destroyed by onion rot Root Bonitization (1-4) 10 mg 45g 0% 4 20 mg 45g 0% 4 40 mg 47g 0% 4

22g 92% 1 33 g 75% 1

Root Biting; 4 = no contamination active compound is ration (%) Plant loss in 7 weeks (G) Average fresh weight of plants after 7 weeks (g) 3 - low contamination 2 = moderate infection 1 - High contamination 40 Active ingredient of the preparation Furan-2-carboxylic 0.01 0 217 45 acid [N- (2- 0.02 0 259 -oxoperhidro-3- 0.04 0 223 Example 8 furyl> 2,6-dimethyl-anilide] Phytophthora paraática var. Eradication of Nicotianae in Sinningia speciosa in potted culture 50 I. Control 'Gierth's Blaue' is a young gorse plant inoculated _ 80 140 11 cm diameter clay pots were planted. The substrate was a 1: 1 mixture of peat culture substrate and sandy compost soil. The pre- 55 II. control After watering, the plants were watered once Not inoculated - 0 239

100 ml of the product at a given concentration. After 3 days, the pots were evenly inoculated with mycelial phytophthora cultures of the week. Example 9 The plants were then kept for 7 weeks in a 60 greenhouse at 22-24 ° C. Eradication of Pythium ultimum by saponification of pelargonium pelargonium

The active ingredient, the amounts used and the results obtained are listed in the following table in 6 cm diameter clay pots Pythium ulti. Highly contaminated with 65 mum reproductive material sub

We loaded -613 strats. The substrate was a mixture of 3 parts peat culture substrate and 2 parts sand. Each pot was poured onto the soil surface with 30 ml of the formulation containing the active ingredient in the concentrations given below. Subsequently, rootless shoot tips of ⁵ "Luisenhof" geraniums (Pelargonium peltatum) were planted in 24 pots in each experiment. The plants were grown szaporítóágyban at 22-25 ° C for 25 days, after which the average plant fresh weight and loss of MEG ¹⁰ rooted seedlings.

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

Active ingredient of the preparation Active ingredient concentration (%) plant Loss (G) Average fresh weight of plants (g) 20 Furan-2-carboxylic 0,005 0 7.3 acid- [3-chloro-N- (2-oxoperhydro-3-furyl) -anilide] 0.01 0 7.1 25 Furan-2-carboxylic 0,005 0 6.2 30 acid [N- (2-oxo-perhydro-3-furyl) -2,6-dimethylanilide] 0.01 0 6.8 35 I. Control Contaminated soil - 83 2.6 II. control 40 Steamed soil - 0 6.8 Example 10 45

Effect of preventive leaf treatment on Plasmopara viticola on vine leaves in a greenhouse

Young cotyledons with 5-8 leaves were sprayed onto freshwater with 50% of the active compound formulation, after the primer had dried, the back of the leaves was sprayed with an aqueous suspension of fungal sporangia (about 20,000 sporangium / ml) and incubated in a greenhouse. 22-24 ° C and preferably in a saturated water vapor atmosphere. From the second day on the humidity of the air

It was brought back to normal for 3 to 4 days (30-70% saturation) and then, for another day, 60 atmospheres of saturated water vapor were provided. The percentage of fungal infested surface of each leaf was then recorded and the mean% effect of each treatment was calculated as follows to evaluate the fungicidal effect. 65% effect =

100 * infection of treated plants - 1ΠΟ infection of untreated plants The active compounds, the active compound concentrations and the results obtained are shown in the table below. Active ingredient of the preparation Drug Concentration (%) % effect Against Plasmopara on grapes * Furan-2-carboxylic acid [N- (2-oxoperhydro-3-furyl) -2,6-dimethyl-anilide] 0,001 100 Furan-2-carboxylic acid [2,6-dimethyl-N- (5-methyl-2-oxoperhydro-3-furyl) anilide] 0,001 100 Furan-2-carboxylic acid [3-chloro-N- (2-oxoperhydro-3-furyl) anilide] 0,001 98 Compare Autumn r N Triklórmetiltioftálimid 0,001 80

Comment:

♦ relative to 100% infestation of untreated control

Example 11

Effect of preventive leaf treatment on Phytophthora infestans on tomato or potato plants in a greenhouse

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 sprayed with water containing the active compound at the concentration of the active ingredient below, and sprayed with which was incubated for about 2 hours in a refrigerator at 11 ° C. Plants were incubated in a high humidity greenhouse at about 15-18 ° C and after about 5 days the percentage of infected leaf areas was determined. The fungicidal effect was calculated as follows.

% effect

100 · infection of treated plants = infection of 100 untreated plants

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The active compounds, the active compound concentrations and the results obtained are shown in the table below.

Active ingredient of the preparation Active ingredient concentration (%) % effect on potatoes * 10 F uranium 2-carboxylic acid [N - 0,005 70 - (2-oxoperhydro-3- furyl) -anilide] 0,001 - Furan-2-carboxylic acid FN 0,005 100 15 - (2-oxoperhydro-3-furyl) -2,6-dimethyl-anilide] 0,001 90 Furan-2-carboxylic acid [2,6- 0,005 95 -dimethyl-N- (5-methyl-2-oxoperhydro-3-furyl) -anilide] összehasonlítószer 0,001 95 20 Mangánetilénbiszditio- 0,005 50 25 carbamate 0,001 30 Furan-2-carboxylic acid [N- 0,005 100 - (2-oxoperhydro-3-furyl) -2,6-dimethyl-anilino] 0,001 86 30 F uranium 2-carboxylic acid [2,6- 0,005 100 -dimethyl-N- (5-methyl-2-oxoperhydro-3-furyl) -anilide] 0,001 86 Furan-2-carboxylic acid [2,3- 0,005 71 35 -dimethyl-N- (2-oxoperhydro-3-furyl) -anilide] 0,001 - Furan-2-carboxylic acid [3- 0,005 100 chloro-N- (2-oxoperhidro- 3-furyl) -anilide] 0,001 - 40 F uranium 2-carboxylic acid [3- 0,005 81 fluoro-N- (2-oxoperhidro- 3-furyl) -anilide] 0,001 -

0.005 67

0.001 0

100% infection

Active ingredientActive strength of active ingredient in potato * _________________ (%) Reference substance Manganese ethylene bis-dithiocarbamate

Comment:

* relative to untreated control.

Example 12

Systemic effects of soil treatment against Phytophthora infes · tans on tomato plants or potato plants in a greenhouse

Formulations containing the following active ingredients were mixed in soil (parts by weight active ingredient / volume), potted in soil, and seeded with young tomato plants with at least two developed foliage or potato plants at least 10 cm in height (e.g. After the desired waiting time (e.g. 3 days), the plants were sprayed with an aqueous suspension of the fungus containing 50,000 to 80,000 sporangia per milliliter, which was incubated for about 2 hours in a refrigerator at 11 ° C. Plants were incubated in a high humidity greenhouse at about 15-18 ° C and after about 5 days the percentage of infected leaf areas was determined. The fungicidal effect was calculated as follows:

% effect

100 · infection of treated plants = 100 --—___________________ infection of untreated plants

The active compounds, the active compound concentrations and the results obtained are shown in the table below.

Systemic effect of Phytophthora infestans on soil treatment in tomato plants

Active ingredient ppm active ingredient 4 days 18 days before inoculation effect * (%)

Furan-2-carboxylic acid [N - (2-oxoperhydro-3-furyl) anilide] 25 5 32 10 75 32 F uranium 2-carboxylic acid [N- (2- 25 60 92 - (oxoperhydro-3-furyl) - 5 27 66 -2,6-dimetilanilid]

Furan-2-carboxylic acid [2,6-dimethyl-N- (5-25)

-methyl-2-oxoperhydro-3-furyl) anilide 5

100 * = 100% untreated control

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Example 13

Healing effect of leaf treatment against Phytophthora infestans on tomato plants or potato plants in greenhouse 5

Young tomato plants with at least two developed foliage leaves or potato plants at least 10 cm high (e. G. 10 developed potato plants from bud cuttings) were sprayed with an aqueous suspension of the fungus containing 50,000 to 800,000 sporangia per milliliter and kept in a refrigerator for about 2 hours. Plants were incubated in a high-humidity greenhouse. After the desired waiting time, the plants were sprayed with the fungicidal compositions of the test concentrations (dripping water) within the duration of the latent fungal infection. After fungal infection on untreated control plants, the percentage of infected leaf areas was determined. The fungicidal effect was calculated as follows:

% effect

100 · infection of treated plants = infection of 100 untreated plants

The active compounds, the active compound concentrations and the results obtained are shown in the table below.

Active ingredient of the preparation

Sprayed active ingredient (%)

Effect of treatment 1 day before inoculation * (%)

Furan-2-carboxylic acid [N- (2-oxoperhydro- 3-furyl) -2,6-dimetilanilid] 0,004 100 75 Furan-2-carboxylic acid [2,6-dimethyl-N- (5- 0,004 100 47 -methyl-2-oxoperhydro-3-furyl) anilides]

összehasonlítószer

Mangánetilénbiszditiokarbamát

0.004 * = 100% infected with untreated control

The composition of the compositions of the present invention is illustrated by the following example.

Example 14 is a surfactant based on weight% cellulose, weight% N-methyl taurine sodium salt and calcium salt of lignin sulfonic acid.

the) 80% by weight furan-2-kaibonsav- [N- (2-oxopeihidro-3-phenyl) -2,6-dimethyl-anilide] 45 10% by weight calcium salt of lignin sulphonic acid, 3% by weight tetraethylene nonyl phenyl ether sulfuric acid monosodium salt, 50 7% by weight colloidal silica, b) 20% by weight 70% by weight 8% by weight 2% by weight furan-2-carboxylic acid [N - (2-oxoperhydro-3-phenyl) -2,6-dimethylanilide], montmorillonite (Tonsil), cellulose, fatty acid condensation based wetting agent, furan-2-carboxylic acid [N- 55 60 c) 10% by weight - (2-oxoperhydro-3-trifluoromethylphenyl) - -2,6-dimethyl-anilide] 60 weight% clay, 1

suly% hard acid,

Patent claims.

Claims (10)

Patent claims. CLAIMS 1. A fungicidal agent comprising at least one furanecarboxylic anilide of formula I - where R 1 is hydrogen or C 1-4 alkyl; and R ₂ represents from 0.005 to 80% by weight of phenyl or phenyl substituted by one or two C 1 -C 4 alkyl or halogen atoms, with one or more customary carriers or diluents, preferably minerals, optionally surfactants and / or other excipients, preferably fatty acid methyl -tauride, calcium salt of lignin sulphonic acid, alkylphenol polyglycol ether and condensation product of lock acids. -9180985 2. An agent according to claim 1, characterized in that it contains as active ingredient fluorane-2-carboxylic acid [N- (2-oxophehydro-3-phthryl) -2,6-dimethylanilide]. 3. An agent according to claim 1, wherein the active ingredient is foran-2-carboxylic acid [N- (2-oxoperhydro-3-furfl) -anilide]. 4. An agent according to claim 1 wherein the active ingredient is furan-2-carboxylic acid [2,6-diethyl-N- (2-oxo-pyridro-3-furyl) -anilide]. 5. The agent of claim 1, wherein the active ingredient is furan-2-carboxylic acid [2,6-dimethyl-N- (5-methyl-2-oxoperhydro-3-furyl) anilide]. et. 15 6. An agent according to claim 1, wherein the active ingredient is furan-2-carboxylic acid [2,3-dimethyl-N- (2-oxoperphydro-3-furyl) anilide]. 7. An agent according to claim 1 wherein the active ingredient is farane-2-carboxylic acid [3-methyl-N- (3-oxoperhydro-3-furyl) anflide]. 8. An agent according to claim 1 wherein the active ingredient is furan-2-carboxylic acid [3-chloro-N- (2-oxoperhydro-3-phenyl) anilide]. 9. The agent of claim 1 wherein the active ingredient is furan-2-carboxylic acid [3-bromo-N- (2-oxoperhydro-3-furyl) anilide]. 10. The agent of claim 1 wherein the active ingredient is furan-2-carboxylic acid [3-fluoro-N- (2-oxoperhydro-3-furyl) anilide]. 1 drawing Responsible for publishing: Director of Economic and Legal Publishing 84.4263 - Zrínyi Printing House, Budapest -10180985 International Classification: C 07 D 307/00, A 01 N 43/08