CS201933B1 - Fungicide - Google Patents

Description

SUMMARY OF THE INVENTION The present invention provides a fungicidal composition which contains, as active ingredient, the ammonium salts of substituted 4-thiocyanophenols.

They are known from the literature as 2-methyl-4-thiocyano-6-bromophenol as an insecticide and fungicide (U.S. Pat. No. 3,389,162) and as fungicide 2-faro-4-thiocyano-6-isopropylphenol (U.S. Pat. No. 3). 389,163), as fungicides alkyl substituted with 4-thiocyanophenols (U.S. Pat. No. 3,202,690), as herbicides substituted with 4-thiocyanophenylalkyl ethers and substituted with 4-thiocyanophenylalkoxyesters (French Pat. No. 1,528,727). Herbicidal, fungicidal, bactericidal and nematicidal active carbamates of 4-thiocyanophenols as well as a process for their preparation are known (Franc. Pat. No. 1,543,418; Svaj. Pat. No. 468,982). Also known as fungicides and insecticides are the carbamates of 2,3,6-subst.-4-thiocyanophenols (CSSR Pat. No. 149,001) as well as their ammonium salts (CSSR Pat. No. 150,063).

We have found that the hitherto unknown ammonium salts of substituted 4-thiocyanophenols of general formula

wherein R 1 is methyl, halogen or nitro, R ₂ is hydrogen, methyl or ethyl, R ₃ is hydrogen or methyl, R 4 is halogen or nitro, wherein in R ₂ and R ₃ there is at most one hydrogen atom and in R _b R ₂ and R ₃ is simultaneously 1 to 2 methyl or methyl and ethyl, X is ethylenediamine, hexamephylenediamine or piperazine are effective as fungicides.

The active compounds according to the invention can be formulated into solutions, emulsions, suspensions, powders, pastes and granules. These are prepared by known methods,. for example by mixing the active ingredient with excipients such as liquid solvents or solid carriers, optionally using surfactants such as emulsifiers or dispersants. When using water as the solvent, an organic solvent may be used as the co-solvent. Suitable liquid solvents are, in particular, xylene and toluene, chlorinated aromatic hydrocarbons such as chlorobenzene, some petroleum fractions, alcohols such as methanol and butanol, strong polar solvents such as dimethylformamide and dimethyl sulfoxide, and also water. As solid carriers, for example, kaolin, alumina, talc, chalk, high dispersion silicic acid and silicates are used. Emulsifiers can be used nonionic and anionic such as polyoxyethylesters of fatty acids, polyoxyethylethers of fatty alcohols such as alkylaryl201933.

polyglycol ethers, alkylsulfonates and arylsulfonates. Suitable dispersants are, for example, lignin, sulphite liquors and methylcellulose.

The active compounds according to the invention can be used with other pesticide active compounds.

The content of active ingredient in the dosage form used can vary within wide limits depending on the intended use.

In general, the formulations used do not contain from 0.001 to 5% by weight, preferably from 0.01 to 0.5% by weight of active ingredient.

The following examples illustrate in more detail, but do not limit the properties of the compounds of the invention.

Determination of effect on Erysiphe polyphaga by spraying on cucumber plants

Cucumber raspberries are sprayed at 500 ppm active ingredient in a volume of 10 ml / 2 vials at the stage of two cotyledons. After drying, the plants are infected with spores of E. polyphaga by dusting and placed in a greenhouse. metal cubicle for incubation. As a control there are untreated plants. Crotothane 25% WP is used as standard.

The test is evaluated at a time when the challenge of the untreated control is about 40 to 60%. Graded: scored area rating up to 5% 4 to 25% 3 to 50 '% · 2 to 100% 1

Determination of systemic effect on Erysiphe polyphaga on cucumber plants

The cucumber plants at the two-leaf stage are placed in sand-filled containers and watered as necessary with Knopp's nutrient solution. On the third and fourth day, a grout of 500 ppm of the active ingredient is applied in a volume of 10 ml / l application. On the fifth day after transplanting, the plants are infected with E. polyphaga spores and placed in a greenhouse for incubation. Controls are untreated plants. Calixin is used as standard. .

The evaluation is carried out at a time when the challenge of the untreated control is 20 to 60%. The assessment shall be carried out according to the scale referred to above.

Determination of fungicidal activity on Phytophtora infestans by spraying tomato plants

Whole tomato plants of the Imun variety grown in the parenisk pod are sprayed with the test substance with an atomizer at a height of 10-15 cm. The application rate is 10 ml / 3 flower pots. Active ingredient concentration 500 ppm.

Treated plants are infected with a conidia suspension after drying with a volume of 3 ml / 2 plants and placed in an incubation chamber with high relative humidity at 18 ° C for 6, respectively 3 days and then transferred to a greenhouse for a further 2 days.

Dithane M-45 is used as standard.

On the fifth day after the infection of the plants, the percentage of infected leaves is determined according to the scale above.

Determination of effect on Erysiphe graminis

Two leaf barley plants are sprayed with the test substance at an active substance concentration of 500 ppm, for a total volume of 10 ml / 2 flask. After drying the plants, they are infected with spores of E. graminis and placed in a humid incubation chamber (15-18 ° C) for 6 days, using Imugan as standard.

After a given incubation period, the% of infested leaf area is determined and expressed on the scale indicated above.

Determination of effect on Sclerotinis fructicola using a slide method

From the prepared spore suspension at a density of 250,000 / ml, pipette 1 ml to 1 ml of the preparation so that the final active compound concentration is 200, 20 and 2 ppm. After thorough mixing, the suspension is transferred to a ring on a slide and allowed to incubate for 24 hours at 20 ° C. After this time, the preparations are fixed with formaldehyde and germination is detected microscopically.

Captan is used as standard.

After a 24-hour incubation, the germination effect is determined and the final evaluation is as follows:

concentration in ppm germination of spores score in points 2 sprouting 4 2 the key 3 20 sprouting 3 20 the key 2 200 sprouting 2 200 the key 1

Compounds were tested:

1. Bis, (2,6-dibromo-3-methyl-4-thiocyanophenol) Ν, Ν-ethylenediamine salt

2. Ν, ΝΝ-ethylenediamine salt bis bis- (2,6-dibromo-3,5-dimethyl-4-, thiocyanophenol)

3. Bis, (2,6-dichloro-3,5-dimethyl-4-thiocyanophenol) Ν, Ν-ethylenediamine salt

4. 1,4-piperazine salt of bis- (2,6-dichloro-3,5-dimethyl-4-thiocyanophenol)

5. Ν, Ν-Ethylenediamine salt bis bis- (2-bromo-3,6-dimethyl-4-thiocyanophenol)

6. Ν, Ν’-ethylenediamine so! bis- (2-chloro-4-3,6dimetyl tiokyanofenolu)

7. Ν.Ν-Ethylenediamine salt of bis- (2,6-dichloro-3-methyl-4-thiocyanophenol)

8. Ν, Ν-Ethylenediamine salt bis bis- (2,6-dinitro-3-methyl-4-thiocyanophenol)

The results of fungicidal activity are shown in Table 1.

Table 1

A compound of the invention E. polyphaga P. infestans E. graminis S. fructicola spray salad dressing First 3.5 3 3.5. 4 2 3 3.5 2.5 2.5 3 Third 3.5 - - , - 3 4th - - - - 3 5th - 3 _ 3 6th - 3 3 4 7th 4 - 4 4 - 8th - - 3 4 - standard 4 4 4 4 4

OBJECT OF THE INVENTION

Claims (1)

OBJECT OF THE INVENTION A fungicidal composition comprising, as active ingredient, the ammonium salts of 4-thiocyanophenols of the formula: ## STR2 ## wherein R @ 1 is methyl, halogen or nitro, R @ ₂ is hydrogen, methyl or ethyl, R @ ₃ is hydrogen or methyl, R @ ₄ is halogen or nitro, wherein the R ₂ and R ₃ are both not more than one hydrogen atom, and R _t, R ₂ and R ₃ are both 1 to 2 methyl or methyl or ethyl group, X is ethylene diamine, hexamethylene diamine or piperazine.