FI68397B - SAOSOM FUNGICID ANVAENDBARA CYKLOPROPANKARBOXYLSYRAANILIDER - Google Patents

Description

RSr7! ΓΒ1 (11) NOTICE.SU 68397

l0 · »UTLÄGGNI NGSSKRIFT

• C (45) Patent granted 10 09 1985 i & rVpj Patent oeddelat * I (51) Kv.lk. * / Lnt.CI. * C 07 D 307/32, A 01 N 53/00 gUQ | ^ || __p || ^ (^^ | ^ Q (21) Patenttihakemus - Patentansfikning 78126¾ (22) HakemlspilvS - Ansökningsdag 21+. 04.78 (FI) (23) AlkupSivi - Giltighetsdag 2¾ .0¾. 78 (41) Has become public - Blivit offentllg 28.1 1.78

National Board of Patents and Registration (44) Date of display and publication. - 31.05.85

Patent and registration authorities in the field of registration and publication (32) (33) (31) Pidetty etuoikeus - Begärd priority 27.05.77

Federal Republic of Germany-Förbundsrepubliken Tyskl and (DE) P 2721 + 786.5 (71) Schering Aktiengesel1schaft, Ber1in / Bergkamen, DE; Mullerstrasse 170-178, D-1000 Berlin 65, Federal Republic of Germany1 (Förbundsrepubliken Tyskland (DE) (72) Ulrich Buhmann, Berlin, Reinhold Puttner, Berlin,

Ernst Albrecht Pieroh, Berlin, Dietrich Baumert, Stock Exchange,

Federal Republic of Germany Förbundsrepubl iken Tyskland (DE) (7¾) Oy Kolster Ab (5¾) Cyclopropanecarboxylic acid used as a fungicide1 -Säsom fungicid användbara cyclopropanecarboxy1cyanide

The invention relates to novel cyclocarboxylic acid anilides of the formula R2 I ^ CH?

CHp- CH-N-CO-CH · ^ I

H1 ^ CH2 I

wherein R 1 represents hydrogen or methyl, and 1 * 2 represents phenyl, or methyl, dimethyl, ethyl, diethyl, diisopropyl, methoxy, ethoxy, fluoro, chloro, bromo, dichloro -, cyano, thiomethyl or trifluoromethyl phenyl.

Several fungicides are already known. Known substances of this kind which have been used in practice are, for example, 5-ethoxy-3-trichloromethyl-1,2,4-thiadiazole (U.S. Pat. Nos. 3,260,588 and 3,260,725) and tetramethylthiuramide disulphide (DE 642,532). However, the destructive effect of these substances on plant disease-causing fungi is not always satisfactory.

68397 2

The compounds of the invention have a surprisingly better fungicidal effect than known substances having a parallel effect and, in addition, are well tolerated by plants and have a sufficiently long duration of action. In addition, since the applications in question do not have a phytotoxic effect in practice, they can therefore be used advantageously in agriculture and in horticulture to control fungi which cause plant diseases.

The compounds according to the invention have far superior fungicidal properties against pests, such as false moths.

In contrast to known antifungal agents which have only a preventive effect, such as N-trichloro-methyl-thiimimide (US 2,553,770, 2,553,771 and 2,553,776) and manganese ethylene bisdithiocarbamate. (US 2,504,404 and 2,710,822), the compounds according to the invention surprisingly have the additional advantage of a curative and systemic effect and therefore also make it possible to control pathogens which have already invaded the plants.

The active ingredient can be used either as such or also in mixtures with at least two structurally different active ingredients of the claimed group of compounds. If desired, other fungicides, nematode poisons, herbicides or other pesticides may be added, depending on the desired purpose.

Suitably, the fields of action according to the invention are used, for example, in the form of powders, spreads, granules, solutions, emulsions or suspensions with the addition of liquid and / or solid carriers or diluents and, if appropriate, wetting, adhesive, emulsifying and / or dispersing aids.

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

Suitable solid carriers are lime, kaolin, chalk, talc, Attaclay and other clays, as well as natural or synthetic silicic acid.

68397 3

Surfactants which may be mentioned are, for example, salts of lignin sulfonic acids, salts of alkylated benzenesulfonic acids, sulfonated acid amides and their salts, polyoxyethylated amines and alcohols.

If the active ingredients are to be used for pickling seed, dyes can also be added to give the pickled seed a more visible color.

The proportion of active substance or substances in the preparation can vary within wide limits, the exact concentration of the active substance used in the preparation depending mainly on the amount of substance to be used, inter alia, for soil or seed treatment or foliar spraying. The preparation contains, for example, from about 1 to 80% by weight, in particular from 20 to 50% by weight, of active ingredient and from about 99 to 20% by weight of liquid or solid carriers and, if appropriate, up to 20% by weight of surfactants.

The novel compounds of the formula I can be prepared, for example, by administering compounds of the formula ch2-ch-nh-r2

H \ II

R 1 wherein R 1 and R 2 are as defined above, react with a cyclopropanecarboxylic acid chloride of formula

/ CH

C1-C0-CH | * ch2 in the presence of an acid scavenger and optionally a solvent, preferably in equimolar ratios, and by isolating the products of the process in a manner known per se.

68397

Examples of acid-binding agents which can be used are organic bases, such as pyridine, triethylamine or N, N-dimethyl-1-aniline, or inorganic bases, such as hydroxides, oxides and salts of alkali and alkaline-earth metals, for example sodium, potassium or calcium. carbonates.

As the solvent, for example, ether, tetrahydrofuran, benzene, ethyl acetate and other solvents can be used, if desired. At the same time, liquid acid scavengers such as pyridine can be used as solvents.

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

Operational tests performed and their results.

A. Limit Concentration Test In the control of Pythium ultimum, 20% of the powdered active ingredient preparation was mixed homogeneously with soil heavily contaminated with Pythium ultimum. 0.5 liter clay pots were filled with the treated soil and 20 grains of "Wunder von Kelvedon" of the silage pea species were immediately sown in each of them. After a cultivation period of three weeks at 20-24 ° C, the number of healthy peas was determined and evaluated (1-4).

The active ingredients, application rates and results are shown in the following table.

5 68397

Active ingredient of the invention - Compound of healthy roots Concentration of peas Evaluation __mg / 1 country__Number_ (1 - 4)

Cyclopropanecarboxylic acid / N- (2-oxoperhydro-2017 4 3-furyl) -anil.di7 40 18 4

Cyclopropanecarboxylic acid / 2,6-dimethyl-N- 10 16 4 (2-oxoperhydro-3-furyl) -20 20 4 anilide} 40 19 4

Cyclopropanecarboxylic acid, β-chloro-N- (2-oxo-20 17 4 perhydro-3-furyl) anilide / 40 17 4

Cyclopropanecarboxylic acid 10 3 L-acid-3-methyl-N- (2-oxo-20 16 2 perhydro-3-furyl) anilide 7 40 16 4

Cyclopropanecarboxylic acid 10-acid-2-methoxy-N- (2-oxo-20,16-perhydro-3-furyl) -anil.di7 40 20 4

Reference substance 5-ethoxy-3-trichloromethyl-10 2 1 1, 2,4-thiadiazole 20 51 40 12 3

Control I

(3 repetitions) aj 1 1

Contaminated land b) 0 to c) 0

Control II

(3 reproductions) a) 19 4 Steam treated b) 18 4 c) 18 4

Root evaluation 4 = roots white, no fungal necrosis 3 = roots white, slight fungal necrosis 2 = roots brown, already more severe fungal necrosis 1 = severe fungal necrosis, roots rotted 6 68397 B. Pickling of sugar beets

The revised sugar cane seeds, species "Dieckmann-Suprapoly", were covered with 20% powdered active ingredient preparations. Ordinary compost soil (Damping-off) was placed in 2-liter clay pots (20 x 20 x 5 cm) and 100 sugar cane seeds were sown in each pot. After a culture period of 18 days in a greenhouse at 19-21 ° C, the number of healthy seedlings was determined.

The active ingredients, application rates and results are shown in the following table.

il 7 68397

Active ingredient of healthy seedling compounds according to the invention amount number _____ g / kg seed ____

Cyclopropanecarboxylic acid 0.4 79 / N- (2-oxoperhydro-3-furyl) -0.879 anilide 1,775

Cyclopropanecarboxylic acid 0.4 70 [2,6-dimethyl-N- (2-oxoper-0.8 7 6 hydro-3-furyl) anilide] 1/6 83

Cyclopropanecarboxylic acid 0.43- [3-chloro-N- (2-oxoperhydro-0.882 3-furyl) -anil.id.i 1.6 1.6 93

Cyclopropanecarboxylic acid 0,4,7β-methyl-N- (2-oxoperhydro-0,8 71 3-furyl) -anilide? 1/6 85

Cyclopropanecarboxylic acid 0.48 ^ 2-methoxy-N- (2-oxoperhydro-0.8 87 3-furyl) -anilide ^ 1/6 87

Reference substance 5-ethoxy-3-trichloromethyl-0.4 26 1,2,4-thiadiazole 0.8 44 1.6 53

Tetramethylthiuram disulfide.i 4.8 21 9.6 50

Control I

(3 repetitions) a) 5

Contaminated land b) 7 c) 6

Control II

(3 replicates) a) 83 Steam-treated soil b) 86 c) 81 _ _ ΤΓ 8 68397 C. Effect of preventive treatment against Plasmopara vitlcola on the surface of vine leaves Young vines with 5-8 leaves were sprayed with water to drain with solutions of said concentration; after the spray dried, a spore colony slurry of the fungus (about 20,000/1 ml) was sprayed under the leaves and immediately thereafter germinated in a greenhouse at 22-24 ° C in an atmosphere saturated with water vapor. From the second day, the humidity of the air was returned to normal for 3-4 days (saturation rate about 30-70%) and then the humidity was maintained at the saturation point of the water vapor for another day. For each leaf, the percentage of the area contaminated with fungi was then recorded, and to indicate the fungicidal effect, the average was calculated for each treatment as follows: 100 x treated contamination “untreated contamination ~% effect”

The results are shown in the following table.

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Young tomato plants with at least 2 developed stem leaves and potato plants (e.g. from cuttings) at least 10 cm high were sprayed with a solution of the indicated concentration to drain water and, after drying, were sprayed with an aqueous suspension of spore colonies of 50,000 to 80,000 fungi. / 1 ml, and germinated for about 2 hours in a refrigerator at 11 ° C. Plants were germinated in a greenhouse at high humidity at about 15-18 ° C and after about 5 days the percentage of contaminated leaf surfaces was estimated. The fungicidal effect was calculated as follows: 100 x treated contamination 100 --- =% effect of untreated contamination

The results are shown in the following tables.

(*

% Effect in potatoes against Phytophthora infestans

Compounds of the invention Concentration (% active ingredient) 0.005

Cyclopropanecarboxylic acid N- (2-oxoperhydro-3-furyl) anilide 95

Cyclopropanecarboxylic acid N- 2,6-dimethyl-N- (2-oxoperhydro-3-furyl) anilide780

Reference substance

Manganese ethylene bisdithiocarbamate 50 (* The effect is calculated on the basis of 100% contamination of untreated controls.

i * 12 68397

% Effect in tomatoes against Phytophthora infestans

Compounds of the invention Concentration _______ (% active ingredient) 0.005

Cyclopropanecarboxylic acid / N- (2-oxoperhydro-3-furyl) anilide 7,00

Cyclopropanecarboxylic acid β-methyl-N- (2-oxoperhydro-3-furyl) anilide 81; klopropaanikarboksyylihappo- ^ 3-chloro-N- (2-oxoperhydro-3-furyl) anilide? 91

Reference substance

Manganese ethylene bisdithiocarbamate 67 (* The effect is calculated on the basis of 100% contamination of untreated controls.

E. Systemic effect of soil treatment against Phytophthora infestans in connection with tomato or potato plants in a greenhouse

The field was mixed with weighed amounts (w / v), placed in plant pots and planted with young tomato plants with at least 2 mature stem leaves or potato plants (e.g. cuttings) at least 10 cm high. After the desired settling time (e.g., 4 or 18 days), the plants were sprayed with an aqueous suspension of 50,000 to 80,000 fungal spores / 1 ml and germinated for about 2 hours in a refrigerator at 11 ° C. Plants were germinated in a greenhouse at high humidity at about 15-18 ° C and after about 5 days the percentage of contaminated leaf surfaces was estimated. The fungicidal effect was calculated as follows: 100 x contamination of the treated 100 ----% effect% contamination of the untreated 68397 1 3

The results are shown in the following table.

Systemic effect of soil treatment against Phytophthora infestans in tomato plants (weight / volume of active substance) (*

According to the invention Active _Effect -% ___ compounds substance, Treatment Treatment ppm 4 days before 18 days before _planting_planting_

Cyclopropanecarboxylic acid N- (2-25 89 85 oxoperhydro-3- 5 70 89 furyl) anilide

Cyclopropylcarboxylic acid / 2,6-dimethyl-N- (2-25 92 82 oxoperhydro-3- 5 40 71 furyl) -anilide] (* The effect is calculated for 100% contamination of untreated controls.

F. Healing effect of leaf treatment against Phytophthora infestans on tomato or potato plants in a greenhouse

Young tomato plants with at least 2 developed stem leaves or potato plants (e.g. cuttings) with a height of at least 10 cm were sprayed with an aqueous suspension of 50,000 to 80,000 fungal spores / 1 ml and germinated for about 2 hours in a refrigerator 11 ° C. The plants were germinated at high humidity. After the desired settling time, the plants were sprayed, with the fungal contamination latent, with the test fungicide concentrate to drain the water. After fungal outbreaks in 14,689,37 untreated control plants, the percentage of contaminated leaf surfaces was estimated. The fungicidal effect was calculated as follows: 100 x contamination of the treated 100 - - =% of effect% contamination of the untreated

The results are shown in the following table.

(*. v Injected__Vaffect -% ____ active Treatment Treatment compounds substance,% before planting 1 day after planting___

Cyclopropanecarboxylic acid / N- (2-oxoperhydro-3-furyl) anilide 0.004 1 00 68

Cyclopropanecarboxylic acid [2,6-dimethyl-N- (2-oxoperhydro-3-furyl) -anilide] 0.004 100 60

Reference substance

Manganese ethylene bisithiocarbamate 0.004 91 0 (* The effect is calculated on the basis of 100% contamination of untreated controls.

68397 15 G. Effect of barley seed treatment against Helminthosprorium species

Barley seeds contaminated with Helminthosporium were treated with 50 mg of active ingredient per 100 g of seed. The seeds were then sown in the ground and germinated in an air-conditioned chamber at + 15 ° C. The result of the experiment was evaluated after 6 weeks, when the seedlings were significantly less contaminated than the plants of the untreated control group.

Compounds of the invention__Effect -% ___

Cyclopropanecarboxylic acid [N-methyl-N- (2-oxoperhydro-3-furyl) -anilide? 40

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

Cyclopropanecarboxylic acid β-ethyl-N- (2-oxoperhydro-3-furyl) -anil.id.i 40 Untreated controls 0 H. Limit concentration test against Pythium ultimum 20% powdered active ingredient preparations were mixed homogeneously with soil strongly Pythium contaminated with the ultimum fungus. The treated soil was placed in 0.5-liter clay pots, and 20 grains of Pepper (Pisuin sativum L. convar, medullare Alef.), Species "Wun-der von Kelvedon", were immediately sown in each pot. After culturing for three weeks at 20-24 ° C, the number of healthy peas was determined and root evaluation was performed (1-4).

The active ingredients, application rates and results are shown in the following table.

Root evaluation: 4 = roots white, no fungal necrosis 3 = roots white, slight fungal necrosis 2 = roots brown, more severe fungal necrosis 1 = severe fungal necrosis, roots rotted 16 683 9 7

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The following example illustrates the preparation of the compounds of the invention.

Example

Cyclopropanecarboxylic acid / N- (2-oxoperhydro-3-furylanilide) (Compound No. 1)

To a solution of 10.62 g (0.06 moles) of 3-aniline perhydrofuranone-2 in 50 ml of pyridine is added, with stirring and dropwise, 6.30 g (0.06 moles) of cyclopropanecarboxylic acid chloride at an internal temperature of 5 to 10 ° C. After stirring for 1/2 hour at room temperature, 200 g of a water / ice mixture are added and the mixture is mixed well. After filtration, wash thoroughly with water and dry in an oven.

Yield 10.25 g = 70% of theory; mp. 104 ° C. In a similar manner, the following compounds of the invention were prepared:

No._Compound_Melting point, ° C

2 Cyclopropanecarboxylic acid [2,6-diethyl-N- (2-oxoperhydro-3-furyl) anilide] 102-103 3 Cyclopropanecarboxylic acid [2-methoxy-N- (2-oxoperhydro-3-furyl)] - anilide7 175 - 176 4 Cyclopropanecarboxylic acid [2-methyl-N- (2-oxoperhydro-3-furyl) - anilide7 108 - 109 5 Cyclopropanecarboxylic acid? 2,6-dimethyl-N- (2-oxoperhydro-3-furyl) - anilidij7 114 - 116 6 Cyclopropanecarboxylic acid N- (2,5-dimethyl-N- (2-oxoperhydro-3-furyl)) anilid 84 7 Cyclopropanecarboxylic acid β-methyl-N- (2-oxoperhydro-3 (furyl) -anilide // 10 09 Cyclopropanecarboxylic acid [4-methyl-N- (2-oxoperhydro-3-furyl) -anilide] 123 4

II

68397

N; o_Compound ____Melting point, ° C

9 Cyclopropanecarboxylic acid 73,4-dimethyl-N- (2-oxoperhydro-3-furyl) anilide / 99-100 10 Cyclopropanecarboxylic acid [2,3-dimethyl-N- (2-oxoperhydro- 3-furyl) anilide 153,113 Cyclopropanecarboxylic acid [2,4-dimethyl-N- (2-oxoperhydro-3-furyl) anilide] 85-86 1 2 Cyclopropanecarboxylic acid [3,5-dimethyl- N- (2-oxoperhydro-3-furyl) anilide 7 103 1 3 Cyclopropanecarboxylic acid [4-chloro-N- (2-oxoperhydro-3-furyl) anilide] 149 - 150 14 Cyclopropanecarboxylic acid 73-chloro-N- (2-Oxoperhydro-3-furyl) anilide 99-100 15 Cyclopropanecarboxylic acid 73-trifluoromethyl-N- (2-oxoperhydro-3-furyl) anilide 104-105 16 Cyclopropanecarboxylic acid β-fluoro - N- (2-Oxoperhydro-3-furyl) anilide 89 89 17 Cyclopropanecarboxylic acid 73-bromo-N- (2-oxoperhydro-3-furyl) anilide 93-94 1 8 Cyclopropanecarboxylic acid , 6-Diisopropyl-N- (2-oxoperhydro-3-furyl) anilide-215-216 19 Cyclopropanecarboxylic acid 72-et Yyl-N- (2-oxoperhydro-3-furyl) -anilide 103 20 Cyclopropanecarboxylic acid {A-ethyl-N- (2-oxoperhydro-3-furyl) -anilide-1 07 21 Cyclopropanecarboxylic acid [4-methoxy- N- (2-oxoperhydro-3-furyl) anilide_7 75 20 68397

No. Compound__ Melting point, ° C

2 2 Cyclopropanecarboxylic acid [4-bromo-N- (2-oxoperhydro-3-furyl) -anilide] 17 144 - 145 23 Cyclopropanecarboxylic acid [4-fluoro-N- (2-oxoperhydro-3-furyl) -anilide / 138 - 139 2 4 Cyclopropanecarboxylic acid 2-ethoxy-N- (2-oxoperhydro-3-furyl) anilide 143 - 145 25 Cyclopropanecarboxylic acid 4-ethoxy-N- (2-oxoperhydro-3-furyl) ) -anilide (nD: 1,4579) 26 Cyclopropanecarboxylic acid 3-chloro-N- (5-methyl-2-oxoperhydro-3-furyl) anilide 95-97 27 Cyclopropanecarboxylic acid / 3-ethyl-N - (2-Oxoperhydro-3-furyl) -anilide / 69-70 28 Cyclopropanecarboxylic acid / 3-cyano-N- (2-oxoperhydro-3-furyl) -anilide / 142-143 2 9 Cyclopropanecarboxylic acid / 3 -thiomethyl-N- (2-oxoperhydro-3-furyl) anilide / (n °: 1.5888) Cyclopropanecarboxylic acid [2,3-dichloro-N- (2-oxoperhydro-3-furyl) ) - anilides / 136 - 137

The compounds of the invention are generally almost colorless, odorless, crystalline substances which have little solubility in water or petrol, but are very soluble in polar organic solvents such as acetone, dimethylformamide and dimethyl sulfoxide.

The starting compounds used in the preparation of the compounds according to the invention are known per se or can be prepared by known methods.

Claims (1)

Cyclopropanecarboxylic acid anilides of the formula f 2 ^ “2 CH„ -CHtN-CO-CH 2 I JLo ^ for use as a fungicide, wherein R 1 represents hydrogen or methyl, and represents phenyl, or methyl, dimethyl, ethyl, diethyl, diisopropyl, methoxy, ethoxy, fluoro, chloro, bromo, dichloro, cyano, thiomethyl or trifluoromethylphenyl.