SU656463A3 - Fungicide composition - Google Patents

Description

The invention relates to chemical plant protection agents, specifically, to a fungicidal agent based on nitrogen-containing heterocyclic derivatives. A commercial fungicide is known, the active substance of which is zinc-9Tylene-1, 2-bis-dithiocarbammate fl. Closer in chemical structure to the proposed fungicide based on derivatives of substituted benzylimidazole 2. However, these fungicides have insufficient activity at low concentrations. In order to find new fungicidal agents with high fungicidal activity, it is proposed to use a nitrogen-containing heterocyclic derivative of the general formula where R is chlorine, fluorine, phenyl or phenoxy, unmixed or once-mixed with chlorine; X is chlorine or a radical 0-J, where R is allyl, propargyl, or benzyl, unsubstituted or once or twice, with chlorine; P - 1 or 2, and its salts, and the content of the active principle in the medium is 0.1-95 wt.%. Some well-known derivatives of gri and ash of the general formula I are obtained by the interaction of alkanols of alkali metals, derivatives of 1 hydroxy-1-phenyl-2-triazolyl-eganasK-Nab, in the presence of a diluent. Other derivatives of general formula I are obtained by reacting 1- (2-hydroxy-2-phenylethyl) -triazoles with a halogen cleaving agent, if necessary in the presence of a diluent. Suitable as a diluent are all inert organic solvents, preferably ketones and ethers. The reaction temperature can vary over a wide range, preferably a boiling point of solvent. The forms of application of the compounds of the formula I are ordinary: powdered preparations, wettable powders, emulsifiable con. centers, granules, dispersions. The proposed tool contains from OD to 95 wt.% The current beginning, preferably 0.5-90 wt.%. The examples below illustrate the fungicidal activity of the proposed agent. Example A. A solution containing the active principle is sprayed with young leguminous plants, which are in the development stage of two leaves, until a droplet is formed. The plants are left in the greenhouse for 24 hours at a temperature of 20 22 ° C and a relative humidity of 70%. Then they are inoculated with an aqueous suspension of the uredospores of the bean rust pathogen (Upomsces) and incubated in a dark chamber for 24 hours at a temperature of 20–22 ° C and relative humidity of 10 O%. The plants are then subjected to intensive illumination for 9 days at a temperature of 2 ° C to 22 ° C and a relative humidity of 70–80%. After 10 days from the inoculation, the extent of the lesion is determined in percent. At the same time, O% means no damage, 10% - plants are completely affected. The results are shown in Table. 1. Table 1% of the lesion (in%) at a concentration of Active starting of the active principle of 0.01%. Continuation of the table. 1 CHg-N (-HNO; 50 7 I fH-CHj-lffj 0 Cl

Example b. Teci with Ef (siptle (cucumbers), defensive action.

A solution containing the active principle is sprayed on young cucumber plants with approximately 3 leaves, J before dropping and left to dry for 24 hours in a greenhouse. For inoculation, cucumber plants are powdered with conidia of the fungus Euphus cictioreacearum.

and placed in a greenhouse at a temperature of 23-24 C and a relative humidity of about 75%.

After 12 days, the extent of damage to the cucumber plants is determined. At the same time, O% means no damage, 1oo% - the plants are completely affected. The results are shown in Table. 2

table 2

C1- 7 5H-CH2-if I, 1

 I VeJ 1/2

(Known)

62

SOjH

ff

f ciH-CHj-Kj nnrog

Cl

(Hseecntho) .Cl

CH-dHgI

0

J (lH.j

/ V (H-CH2-1J I

0

one (

O-f- - CJ

31

0

9

HSOj

25

6564638

Continued table. 2

/-one

"11- / usn- (1

- y-and-

ABOUT

j / CH-CH2- "1

y

0 cl

59

fiH-CH2I-VTcSI

$ 0, N

0

SOsH

di- / USN-CH - I

 -U-SEI

about

Uno

/ TS-N

CHn-F I J

-NUGE:

/ -

22

CH-CH -K J 0

8o, H

9

Active principle

65646310

Continued table. 2

The degree of damage (in%) at the concentration of the current beginning,%

about.

O.OOOb

O, 0025 r, OOOb2

/

  CH-dHo-H 1 -.

Ci

t

€ i «1

/ e-H

C11-CH2-K I 1 and -uJsJ

F

el

y H-CH2-K I

i- / i4r

about

HMO,

about

SOxH So, H

about

NIJO.

62

ftho:

J-dH- (H2- / J

eleven

about

ABOUT

Cl - f VCH - (I -HSOj

Cl

0

eleven

Active principle

656463D.2

Continued tab, 2

The degree of damage (in%) at the concentration of the active principle,%

CH-tiHg-lir

U oi

25

til- /

"H-CHj-fffj

rfl-

Cl Example B. Test with FustcEadium (Blony scab), defensive action. The solution containing the active principle is sprayed with young young saplings of the Blony, entering the shadies in the development of 4 6 leaves, until droplets are formed and left for 24 hours at a temperature and relative humidity of 70% in the greenhouse. Then they are inoculated with a water suspension of conidia of the Shibloni vapor exciter (Fusic & cjdiuni dendiit.icum Fvjcic) and incubated for 18 hours in a chamber at a temperature of 18–20 ° C and relative humidity of 1OO%. The plants are then re-incubated in the greenhouse for 14 days. After 15 days from the inoculation, the percentage damage to the seed is determined. At the same time, O% means no damage, 1% germs are completely affected. The results are shown in Table. 3. Table 3: Degree of damage (in%) at a concentration of Acting onset of acting on the beginning of O.OOO62%

О Continuation of table. 3 OH-CHg-I ITff-sJ eS-OHo-I. 22 Val 0-CH2-Cll llH2 ch-Ch-J I I-the importation of CHa-dsdH CH-SZy-G J

N-SSCH-1 / V

59 0-C4H9

(Known

Xt / 2

(Known)

55 Cl

9

(il

13656463

Continued table. 3

"Gt

: i-f VfH-tiiij-iJ, J i cu

14

Continued table. 3

ten

15

20

iJll-JH9-l I I

N,

(Jh

Cl

SO, H

SO, H

$ 0, K

Example G. Tesg with a programer for inoculum. Striped patches of barley (caused by mycosis seeds).

For seed dressing

barley naturally affected by DrechsEerot §1 ash1pds rst hiva with a pickling agent in a closed glass bottle. The seed placed on wet filter paper in the closed

Petri dishes, incubated in the refrigerator for 10 days at a temperature of -. round 4C. At the same time, barley sprouting, as well as mushroom spores, begin to grow. Pre-sprouted barley - 2 50 grains - are then sown to a depth of 2 cm in standard soil of Frustorfer variety and kept in a greenhouse at 18 ° C, exposed to light for 16 hours daily. For 3-4 weeks signs of striped barley patchiness.

After this time, the number of affected plants in the proent of germinated plants is determined. The effective principle is the more effective the smaller the number of affected plants.

The results are shown in Table. four.

15

5se P1 otra6lidani

Zn

thirty

thirty

N

(JH-CjHj-N I -HBTOj

IV-

0

I

SN: 2- (

- (USN-CH - I

thirty

/ Iir

0

An2- (n (yg

656463

lo Table

60.6

5O, O

0.0

5.0

a / 2

Example A. Mildew Test with Barley -Er-vsiptie gr jiminis ag-tiordei (systemic effect).

The active ingredient is applied in the form of a powdered pickling seed to the {terial agent.

To treat the seed, the seeds are exchanged with a drug in a closed glass bottle. 3 x. 12 grains of seed to a depth of 2 cm are sown in flower pots filled with a mixture of 1 ob.h. Frustorfer’s sorghum standard soil and 1 part by volume quartz sand. Germination and germination are carried out under favorable conditions in a greenhouse. After 7 days after sowing, the barley plant with the developed first leaf is powdered with fresh spores of Erasiphe gframinis van tiordei and at a temperature of 2122 ° C and a relative humidity of 8О-9О%, they are exposed to exposure every day for 16 hours. Powdery mildew is formed on the leaves for 6 days.

The degree of damage is determined as a percentage of the degree of damage to untreated control plants. In this case, 0% means no damage and 100% damage rate, similar to that of the untreated control. The active principle is the more effective, the less defeat powdery mildew.

The results are shown in Table. five,

. 17

Without dressing

$

sn2-nns $

I

CH2-UHCS /

I

{Known}

lJHCSv

Zn

.

II

$

(Known)

, (31 „

five/

i

CH-YN-H- I

NIO:

about

((H

.C1

,

i-f us-bn-I

but ij

CH2-CHCH.2 C1

H)

About C1

/ C1

/ -f

CH- (JH2-N 25

: NC .I

65646318

Table 5

100.0

1O

100.0

ten

100.0

ten

0.0

lO

0.0

lO

0.0

ten

0.0

ten

o.o 65 Example B. Test with seedling treatment (mealy dew on cereals), protective effect. With a view to determining the protective efficacy of the proposed remedy, one-year-old young barley plants from the Ashzeb variety are sprayed with an active ingredient to the moisture content of the dew. After drying, the plants are barbed with spores Er Jsiplie gfOHifiinis var. tiordei. After 6 days of stay, the temperature is 21-22 ° C and the temperature at

No processing

I € I, –NN € $

NCH-1GN € $ /

and

$ ((Notify)

I, Zn

en - nse

(HsSsemHe} C1

6

Table

100.0

0.025

1oo, 0

0.025

100.0 320 air humidity 80-90% determine the defeat of plants by powdery mildew. The degree of onpone / ftKiT damage as a percentage of the degree of damage of the untreated control. At the same time, 0% means no damage, 100% means a degree of damage similar to that of the untreated control. The active principle is the more effective, the less defeat powdery mildew. The results are given in “abl. b.

0.026

0.0

tiHrf-N (

"VJ

dj

0.0

0, O25

0.025

0.0

21

22

656463

Continued gab. 6

NGOs:

0.025

0.0

1- {Y Н- (iuf-lfj

NZHOZ

OU -

di4 I

 . | i

Example G. A seedling test (rust of grain crops), protective action.

In order to determine the protective efficacy of the proposed inoculum agent, one-year-old young wheat plants of the variety M-ichigctti Amfeer with a suspension of uredospores Puccinia reconditaa 0.1% aqueous agar. After drying the spore suspension, the wheat plants are sprayed with this preparation of the active principle to the dew moisture and placed for incubation for 24 hours at a temperature of approximately 20 ° C and 100% relative humidity of air.

0, O25

0.0

0.025

0.0

For about 10 days of plant life at a temperature of 2 ° C and humidity of the air 80-90% estimated {Fayut degree affected

35 plants with rust pusguli. The extent of the lesion is determined as a percentage of the degree of lesion of the untreated control. At the same time, O% means no damage, 10% - the degree of damage similar to

40 degrees of untreated control damage. The active principle is the more effective, the less rust damage.

45 The results are shown in Table. 7

65646324

23

Conyentrapy acting on the beginning of the beginning in the spray liquid, wt.%

processing

$

Zn

NHCS

(Known)

YN, -zh € &.

X

“No-BIRD /

/ Gk

{ff-CHj-ir (

one

/ -Ir Cff-CH2- I -HNOg

h

Table 7

The degree of nopameHfitet,% of untreated control

100.0

0, O2S

93.4

93,8

0.025

0.025

16.3

0.025

0.0

0.025

55.0

f "-" "- J

Cl

0.0

0.025

Example 3. The test with Podosptidercjl powdery mildew of blony (hardwired deist).

The solution containing the active principle is sprayed with young baby ravens, which are in the development stage of 46 leaves, before the formation of droplets. Grow LIA for 24 h at 2СГС

and relative air humidity of 70% is left in the greenhouse. Then they are inoculated by dusting with powdery powdery mildew pathogen 55 (PocJosptiaera Veicotrictioi 9c t1) and placed in a greenhouse, in which the temperature is maintained at 21-23c and the relative humidity of the air at approximately 7O%. After 10 days after inoculation, the degree At the same time, 0% means no damage, 100% - plants are completely infected. The results are shown in Table 8. Table 8 JH-CH2-N I til {I’ll see} 25 j rorOg Continuation of Table 8. 2/7 "H2 -N T 11 / I -J Jl Example I. Test with mycelium growth. Neither it is mixed in a nutrient medium 1 O ppm with a solvent. The concentrate is thoroughly mixed with a liquid medium cooled to a temperature of 42 ° C and poured into Petri dishes 9 cm in diameter. In addition, control plates are prepared without preparation. Days of the nutrient medium are hardened plates infected with the fungi indicated in Table 9. They are incubated at a temperature of approximately. Evaluation is carried out depending on the growth rate of the fungi after 4–1 days. For evaluation, the radial growth of the mycelium on the treated nutrient media is compared with the growth of the mycelium on the congeners. Fungi growth is assessed according to the following scale, score: 1 - no growth Up to 3 - very strong under-growth Growth up to 5 - moderate growth retardation Up to 7 weak growth retardation 9 - growth corresponds to the growth of the untreated control. The results are shown in Table. 9.

Yu

with

yu yu

Yu

WITH

WITH

I

Yu

About K | H

Yu

about

S

B

V

III

w with.

-ty

to

w-oh;

Yu

to

u n

Yu

I n

I n

with

with

with

with

with

Yu

1L

I

n

Yu I

with

yu yu

Yu

3565646336

Thus, the proposed compound is where R is chlorine, fluor, phenyl or phenoxy,

neither have high fungicidal active-unsubstituted or once-mixed

with low concentrations of chlorine;

Claims (1)

Claim X — Chlorine or 0-R, where C is a fungicidal agent containing deisallily, propargyl and / and benzyl, an unsubstituted principle based on nitrogen-containing or single- or double-substituted heterocyclic derivatives, as chlorine; also an additive selected from the group of Tver-P - 1 or 2; respiratory and liquid carriers, between tea and its salts, and the content is effective from the fact that, in order to increase the 10th beginning in the medium is fungicidal activity, it contains 0.1 to 95 wt.%. as a nitrogen-containing heterocyclic derivative of the compound for-forma-Sources of information, taken in expulsion during examination - (1N YNO -: / 1 l.Ptivtopo (i1ioEog: 5f, 1113.1963. -J, I; jfJ2. US Patent J 3679697,  . Hkl 260-309, 1972.