SU793354A3 - Fungicidic agent - Google Patents

Abstract

Anilides of formula (I): (where R1 is halogen, 1-4C alkyl or alkoxy; R2 is H, halogen, 1-3C alkyl or 1-4C alkoxy; R6 H, halogen, or 1-3C alkyl; R6 is H or methyl; provided that the total C atoms in R1,2,5,6 is not >8; X is -CH2- or -CH(CH3)-; R3 is R', R" and R" are H or (m)ethyl; R4 is 1-6C alkyl, 2-5C alkenyl, or 3-7C cycloalkyl opt. substd. by CN or SCN) are plant growth regulators and microbiocides, esp. active against pathogenic fungi.

Description

(54) FUNGICIDE MEANS The invention relates to agricultural pest control chemicals, specifically to the use of a fungicide based on derivatives of N, N-substituted anilines. Known N-benzoyl-N- (3,4-dichlorophenyl) -al nina ethyl ester, which is closest in structure to the proposed, having herbicidal activity 1. It is known that manganese salt N, M-ztilenbisdithiocarbamic acid possesses antifungal activity {2. However, these compounds do not possess sufficient fungicidal activity for diseases of tomatoes, grapes, barley. The purpose of the invention is to find new fungicidal agents based on derivatives of N, N-substituted anilines with high fungicidal activity. This goal is achieved by using a fungicidal agent containing as derivatives of an N, N-substituted aninu a compound of the formula CH-COOR, C-R methyl, methyl, propyl, tert-butyl, and -butoxy; hydrogen, methyl, ethyl, isopropyl, methoxyg sec-butoxy group, chlorine; methyl; CS-GS - cycloalkyl, Cr-Cz-alkenyl, rhodanomethyl, Ci-Ce-alikl "pentyl, diethylmethyl, dimeshtwinip; RS and Wb - hydrogen, methyl, chlorine. A compound of the formula T can be obtained by various methods, for example, by anilating the corresponding N-alkoxycarbonylethylaniline carboxylic acid or its reactive derivative.

3.793354

The reaction is carried out in conventional solvents at a temperature of from 20 to 120 ° C.

In this way, an N- (l-methoxycarbonylethyl) -cyclopropylcarbonyl-2,6-dimesh1ashshin (compound T) is obtained.

51.8 g of a- (2,6-dimethylanilino) -propionic acid methyl ester in 200 ml of absolute toluene with stirring at room temperature were mixed with 31.3 g of 1shclopropanecarboic acid chloride

50 MP absolutized toluene. After adding 2 ml of dimethylformamide mixture

heated refluxed for 2 hours and then the solvent and excess piclopropanecarboxylic acid chloride were distilled off in vacuo. By trituration with a small amount of petrol of the other ether, the remaining oil led to crystallization. After recrystallization in a mixture of toluene - petroleum ether, compound No. 1 melted at 84-87 ° C.

Similarly, the following compounds of the formula T (RI in 2-position; Pu CH3; RS and RS H), presented in b. 1 and 2.

Table 1

(RI is 2-position; Rj: .6-position; Rs — CHj)

table 2

28 CH 2 CH 3 3 CH 3 S CH 2 29 CH 3 CjH 3-CH 3 30 CH 3 CH 3 4 CH 3 CH 3 CH 3 4

Compounds of preparations based on compound T are ordinary: powders, emulsions, granules, etc. The content of active substance in the product is from 0.1 to 90%.

The following examples illustrate the fungicidal activity of the proposed compounds.

In the experiments, the following compounds were used as comparative substances: Maneb - D Manco ceb - E

Fentin

acetate - F Folpet - G

Example. Action against Phyto phtora infestans on tomatoes.

TA Remaining safety

Red gnom tomato plants of the variety after three weeks of cultivation and after spraying with a broth containing 0.06% of the active substance (obtained from the processed up to the wetting force of the active substance), and drying are infected with a suspension of Phytophtora infestens.Pac shrubs are then placed in a climate chamber for 6 days at 18 -20 ° C and high humidity, which is created by artificial Fog mist. After this time there are tapicles on the leaves. Their number and size serve as a measure of the evaluation of the tested substances.

I B. Therapeutic actions.

Red gnom tomato plants, after three weeks of cultivation, are sprayed with a suspension of zoospores of the fungus and incubated in a chamber at 18–20 ° C and saturated. air humidity. Moistening is interrupted after 24 hours. After the plants are dried, they are sprayed with a bleszhom, which contains a biologically active substance prepared in the form of a wettable powder at a concentration of 0.06%. After drying, after spraying, the plants of oyuv are placed in a moist chamber for 4 days. The number and magnitude of the typical spots on the leaves after this time serve as a measure of the activity of the test plants.

Ii. Safety-system action.

Biologically active substances prepared in the form of a wetting scraper in a concentration of 0.006% (with respect to the volume of the soil) are applied to the soil surface of red gnome tomato plants grown to the age of three weeks. After a period of three days, the lower side of the leaves of the plants is sprayed with a suspension of zoospores.

They are then held for 5 days in a cabin with a constant small-drop spraying at 18–20 ° C, and saturated, Tlsip. 184-189 / 0.03 Torr -CH CH-CH3 T.KIP. 128-129 / 0.03 door -SY CH-CH3 T, kip. 138-140 / 0.1 Torr-CzH7 (n) TjcHn. 147-149 / 0.03 Torr Tjcm. 172-174 / 0.02 Torr humidity. After this time, typical spots are formed on the leaves, the number and value of which are used to evaluate the activity of the test plants. Action rating: 0% 0% damage 1% 5% damage

EXAMPLE: e: gooo m7d .; // LLP ppm 2 defeat 20-50% 3 defeat 50% (inactive) was not tested The results are presented in Table. 3. Table 3

PRI mme R 2. Action against Plasmo- .para viticola on grapes.

A.. Residual-protective action.

Chasselas grapes are grown in the greenhouse. In stage 10 of the sheet, 3 plants are sprayed with broth prepared from the biologically active substance in the form of a wettable powder (0.06% of the biologically active substance). After the plaque dries, the plants on the underside of the leaves are uniformly infected with a suspension of fungal spores. The plants are then kept in a humid chamber for 8 days. After this time, there are distinct symptoms of the disease on the control plants. The number and size of the infection sites on the treated plants serve as a measure of the activity of the test plants.

B. Therapeutic action.

Cuttings of Chasselas grapes are grown in a greenhouse and in a 10-leaf stage they are infected with a suspension of Plasmopara viticola spores on the underside of the leaves. After 24 hours of incubation in a humid chamber, the spreading solution is sprayed with 0.06% biodegradable broth; a substance that is prepared from a wettable pest of a biologically active substance. The plants are then incubated for 7 days in a humid chamber. After this time, symptoms of the disease appear on the control plants. The number and size of lesions on treated plants serve as a measure of the activity of the test plants.

Assessment of the effects: O damage 0–5%

1 lesion 5-20%

2 defeat 20-50%

3 affected 50% (inactive)

- not tested The results are presented in table. four.

Table4

. I i

  -,

 ....- .-- - / 93354

II

Grade in Test A

Connection number

thirty

32

f

E

F

G

t2 Continued table. four

Score in test B

2 3 3 3/100 MD

PRI me R 3. Action against Erysiphe granunis on barley.

Residual-scorching action.

Barley plants about 8 cM in height are sprayed with a broth for pressing {1 skimming, prepared from a wettable powder of the biologically active substance (0.02% of the active substance). After 48 hours, the treated plants were sprayed with fungal conidia. Infected barley plants are placed in a greenhouse at about 2–2 ° C and fungal damage is assessed after 10 days,

Assessment of the effects: O damage 0–5%

1 lesion 5-20%

2 defeat 20-50%

3 defeat 50%

(inactive) - not tested. The results of the test.

Grade3 1 1 1 1 O 1 1 1

Thus, the proposed compounds have a high FZ nicidal activity.

Claims (1)

SUMMARY OF THE INVENTION A fungicidal agent containing an active principle based on derivatives of Ν, Ν-substituted anilines and an additive selected from the group of carrier, diluent and filler, characterized in that, in order to enhance the fungicidal action, it contains 25 a derivative of Ν, Ν -substituted aniline compound general formula TO/ / ^CH 3 Rc g- TO\ / CH-COORj thirty )> Xs ^ cr ₄ II Rg. 0 where R _t is methyl, ethyl, isopropyl, tert-butyl, n-butoxy; R ₂ is hydrogen, methyl, ethyl, isopropyl, methoxy, sec-butoxy, chloro; R ₃ is methyl; R ₄ is C ₃ -C ₅ cycloalkyl, C ₂ -C ₃ alkenyl, rhodanomethyl, C] -C ₃ alkyl, n-pentyl, diethylmethyl, dimethylvinyl; R _s and R ₆ - hydrogen, methyl, chlorine, and the content of the active substance in the tool is from 0.1 to 90%.