SU1245251A3 - Fungicide - Google Patents

Abstract

Novel imidazolylpropionitriles of the general formula <IMAGE> in which R represents an aromatic hydrocarbon radical that is unsubstituted or substituted by one of more of the same or different substituents selected from halogen atoms, (C1-C4)- alkyl, (C1-C4)-alkoxy and (C1-C4)-alkylthio radicals and trifluoromethyl and nitro groups, and R1 represents a (C1-C10)-alkyl, (C3-C8)-alkenyl, (C3-C8)-alkynyl or phenylalkyl radical each of which is unsubstituted or substituted by one or more of the same or different substituents selected from halogen atoms, (C1-C4)-alkyl, (C1-C4)-alkoxy and (C1-C4)-alkylthio radicals and trifluoromethyl and nitro groups, and their acid addition salts with inorganic and organic acids, possess a fungicidal, growth-regulating and bactericidal action.

Description

The invention relates to chemical plant protection agents, specifically to a fungicidal agent based on npW 2-phenyl-3- (imidazol-1-yl) propionitrile,

The aim of the invention is to increase the fungicidal activity of the agent.

The proposed fungicidal agent is obtained by simply mixing the components: a 2-phenyl-3-imidazol-1-yl-propionitrile derivative of the formula

-N:

J (1)

where R is phenyl, 2- or 4-chlorophenyl, 2,4-dichlorophenyl, 2-methylphenyl; R, is n-butyl, n-hexyl, allyl,

benzyl;

or its hydronitrate, kaolin, silicic acid, calcium ligninsulfonate and sodium salt of N-methyl-N-oleyl taurine.

Compounds (G) are obtained by reacting imidazole with propionitrile of formula

ORl

R-C-CH2Y

CN

where R and R, have the indicated meanings, a) is halogen, preferably chlorine, ejpoM, iodine; alkylsulfonyl-hydroxy or arylsulfonyloxy group, preferably methyl, ethyl, propyl and trifluoromethylsulfonyloxy, benzylsulfonyloxy, p-toluenesulfonyloxy.

The reaction temperature can be changed.

over a wide range, preferably 1 00-200. The interaction is carried out at normal or elevated pressure. The reaction is carried out with an excess of imidazole in a solvent or in the presence of t.

VII of a strong base, preferably sodium hydroxide and potassium hydroxide.

As solvents, substances which are inert with respect to the reaction components, preferably polar, aprotic solvents — dimethylformaleide 5, dimethyl acetade — and methyl pyrrolidone, benzonitrile, and high boiling aromatic and aliphatic hydrocarbons — toluene, xylene, chlorobenzene — are used as solvents.

. The following compounds of formula (1), presented in Table 1, are prepared by this method.

Table 1

pionitrile (B) or its hydronitrate (A). cid efficiency (/ o) according to the formula

100

The defeat of the treated plants The defeat of untreated plants

Continued t; ebl.

100

Example 2. Young tomato plants were sprayed with the substances indicated in c. Table 3 concentrations After the sprayed layer had dried, the treated plants, as well as untreated plants, were contaminated by spraying a spore suspension (about 1 million in 1 ml of fruit juice solution) of the causative agent of gray mold bofrytis cinerea and: kept in a wet state for approximately

drops of the compounds with the indicated concentration were sprayed on the back of the leaves with an aqueous suspension of fungal spores (about 20,000 per ml) and immediately incubated in a greenhouse at 22-24 ° C in an atmosphere of saturated humidity. From the second day, for 3 and 4 days, the air humidity was kept normal (30-70% of the Nascene) and then the atmosphere of saturated steam was maintained for a day. Immediately after that, on each sheet, the percentage of spots damaged by the fungi was noted and the efficiency was determined as in Example 1. The data are presented in Table 4.

T a b l and c a 4

0.025 0.025 0.025 0.025 0.025 100

98.3 92.5 73

82 94.6

15

20

Example 4 barley untreated with the consumption of an effective substance, the seeds were sown in germinated at a temperature of about 20 ° C. Fresh green was sown with Erysiphe gramini for a week was noted, the leaf surface Fungicide effect was determined as indicated

Defeat treated samples. „,.

The defeat of untreated samples The data are presented in table 5. The effect of fungicide on barley was valued after germination of plants. the assessment was carried out according to the following scheme: About half to 30; 1 90% destruction Example of the 5th solution from water (1: 1) by placing a flask with a volume of 100 g powdered compound (I). Whether this is polluted by digitatum. Then, at 22–24 ° C, the evaluation is on the surface of the solution. Grade: bov, 1 separate on the surface, 2 nos covered with gri surface covered with 30-60% surface, 5 60-100% with mushrooms.

2 80% destruction, 3 70% destruction, 4 60% destruction, 5 40% destruction, 6 40% destruction, 7 30% destruction, About 20% destruction , 9 10% destruction, 10 intact.

The data presented in table.5.

Table5

Continuation of table 4

Example 4. Untreated or pickled barley seeds with consumable rates of I00 g of effective substance per 100 kg of seeds were sown in pots with the ground and germinated in a greenhouse at a temperature of about 20 C. After the formation of the first green leaf, the plants were infected with Erysiphe affected mildew graminis plants. A week later, it was noted how many percent of the leaf surface is affected by the mildew. The fungicide efficacy (%) was determined as indicated in Example 1.

samples

Example 5 20 ml of a nutrient solution from grape juice and water (1: 1) were placed in a 100 ml glass flask and mixed with the powdered final formulation of compound (I). Immediately after this, the Penicillium digitatum was pollinated by spores. Then for 5 days at 22-24 ° C, the development of fungi on the surface of the nutrient solution was evaluated. Assessment: No fungi growth, 1 individual colonies of fungi on the surface, 2 5-10% of the surface is covered with mushrooms, 3 10-30% of the surface is covered with mushrooms, 4 30-60% of the surface is covered with mushrooms, 5 60-100% of the surface is covered with mushrooms.

The compounds, their concentrations in the nutrient solution and the results are shown in Table 6.

Table 6

Continuation of table 6

-, - .. i.-,

eleven

13

14

15

sixteen

17

nineteen

20

21

22

A (known)

0,0005 0,001 0,0005 0,001 0,0005 0,001 0,0005 0.001 0,0005 0.001 0,0005 0.001 0,0005 0.001 0,0005 0.001 0,0005

0.001 0.0005

 0.001 0.0005 0.001 0.0005 O, -001 0.0005 0.001

4 1 o

about about about 1

oh oh oh oh oh 1

. oh oh

oh oh

oh oh oh oh

five

four

Example 6: The shoots in growth were sprayed with a Ventiriu inaegua5 lis snore suspension (330000 in 1 ml) and immediately covered with a plastic bag to keep it moist. Plants H 1 were in partial shade. Through Zdr, the bags were removed. After 7 days, 10 scientific research institutes were sprayed with a fungicide preparation at the concentration of the active ingredient O, 1%. After a further 1.5 pedals, the number of block scabs on the affected surface of the leaves was determined

15 in terms of prod- ucts, which in the case of untreated samples was 99%. EsfectiE1Nost processing was calculated as in example 1. The data are presented in a table, 7,

20, T. a b l and c a 7

25

thirty

35

40

45

50

55

Example 7. The seeds of plants with artificial damage to Helmint-hosporium sativtim were pollinated by the proposed remedy with a consumption rate of 50 g of an effective substance per 100 kg of seg. In each experiment, treated or untreated seeds in the amount of 2 g were sown in plastic pots, 6, 5 cm. Sand was used as a substrate. For the experiment did 2 repetitions. The pots were placed in the chamber of plant growth at 15 ° C. After 4 weeks, the prostate plants had a stem defeat in the leaves. From the average values, the fungicidal efficacy of Example 1 was calculated. The data are presented in Table B.

Table B

Compound

according to

the invention.

Effectively against Helmin-hosporium sativum,%

19 22

100

100 100

Control (unprocessed)

Example 7. The seeds of plants with artificial damage to Helmint-hosporium sativtim were pollinated by the proposed remedy with a consumption rate of 50 g of an effective substance per 100 kg of seg. In each experiment, treated or untreated seeds in the amount of 2 g were sown in plastic pots, 6, 5 cm. Sand was used as a substrate. For the experiment did 2 repetitions. The pots were placed in the chamber of plant growth at 15 ° C. After 4 weeks, the prostate plants had a stem defeat in the leaves. From the average values, the fungicidal efficacy of Example 1 was calculated. The data are presented in Table B.

Table B

Effectively against Helmin-hosporium sativum,%

100

100 100

98.5 98

Example 8. Action against Pseudomonas phaseolicola of in vitro fatty pathogen pathogens. Bio-malt agar after heat sterilization was cooled before and then mixed with the test substances to obtain aqueous preparations and pour into a polymer Petri dish. After solidification of the nutritious earth of the cup. With the treated agar and the cup with the non-working Radial p Radial sp

The inhibitory effect of the 250 ppm effective substance on agar against Pseudomonas phaseolicola is presented in Table. 9.

Table 9

100

1 2 5

71

71 86

Editor A.Dolinich

Compiled by V. Maximov Tehred L. Oleinik

3929/60

Circulation 679 Subscription

VNIIPI USSR State Committee

for inventions and discoveries 113035, Moscow, Zh-35, Raushsk nab., 4/5

Production and printing company, Uzhgorod, Projecto st., 4

in processed in the untreated

Ny agar as a control sample was infected with Pseudomonas phaseolicola fatty pathogen suspension. in the center with a vaccine. The bags were then incubated at 22 ° C. After 2.5 weeks, the radial spread of the grown bacterial colonies was measured. From the average obtained from two repetitions for each experiment, the percent inhibitory effect was calculated using the formula

Goo

20

Thus, the proposed fungicidal agent has a high 30 fungicidal activity at low concentrations.

Proofreader M. Pojo

Claims (1)

A FUNGICIDIC AGENT in the form of a wettable powder containing the active ingredient - a derivative of 2-phenyl-3- (imidazol-1-yl) -propionitrile, a carrier - kaolin, silicic acid, a surfactant - a salt of ligninsulfonic acid, characterized in that, with In order to increase the fungicidal activity, it contains a compound of the formula 0R1 R-C- sn I CN where K is phenyl, 2- or 4-chlorophenyl, 2,4-dichlorophenyl, 2-methylphenyl; R ₁ - n-butyl, n-ge-sil, allyl, benzyl, or its hydronitrate, as a salt of ligninsulfonic acid - ligninsulfonate .calcium and, in addition, as a surfactant oleyltaurin in the following ratio of components, May. 7>: Specified Ingredient20 Kaolin65 Silicic acid Calcium Ligninsulfonate4 Sodium salt of N-methyl-N-oleyltaurin I SU 1245251 AZ