SU727107A3 - Fungicidic agent - Google Patents

Abstract

Cyclopropanecarboxanilides have the following formula <IMAGE> in which R1 is hydrogen or C1-C4-alkyl, R2 denotes an aromatic hydrocarbon radical or an aromatic hydrocarbon radical which is substituted one or more times by identical or different substituents comprising C1-C4-alkyl, C1-C4-alkoxy, C1-C4-alkylthio, halogen, trifluoromethyl, nitro, C1-C4-alkoxycarbonyl, C1-C4-alkylcarbonyl and/or cyano, and n denotes the number 1 or 2. The compounds of the formula I are prepared by reacting a cyclopropanecarbonyl chloride with an appropriate 3-anilino-2-perhydrofuran. Fungicides contain, as the active component, at least one new compound of the formula I.

Description

one

This invention relates to chemical plant protection products, specifically a fungicide based on anilide derivatives.

Commercial preparations of fungicides, such as tetramethylthiudecylphide, ethyl ene bis dithio and manganese arbammate, are used to combat phytopathogenic fungi I.

However, these drugs have an unsatisfactory effect on a number of fungi, such as phytopthora infestans, Pythium nitimum.

It is also known that the active substance of which are furananilide derivatives, which was molded using conventional additives — a filler, a carrier 12.

However, this tool with low doses of the drug has insufficient biological activity.

The purpose of the invention is to find a new fungicidal agent with enhanced biological activity.

This goal is achieved by using an agent containing, as an active substance, co-linking.

(I)

 - CO - SI-CH 9

sn.

ЧВ2) п

in which R is hydrogen or methyl; RJ - C-C alkyl, chlorine, bromine, methoxy, ethoxy, thiomethyl, cyan; p 0-2,

in the amount of 1-80 wt.% and the additive selected from the group of: carrier, filler.

Forms of application are usual: powders, granules, solutions, emulsions, suspensions. They are prepared by conventional methods - common with the manufacture of pesticide formulations,

The compound of formula I is prepared by reacting the appropriately substituted anilinoperofuranone with cyclopropanecarboxylic acid chloride in the presence of solvents and acid acceptors.

Reactions conduct. T at temperatures from -10 to 120 ° C.

Example 1 describes a method for producing N- (2-oxoperhydro-3-furyl) anilide of cyclopropanecarboxylic acid. Compound 1).

Example 1. To a solution of 10.62 (0.06 mol) 3-anilinopergidrofura nona-2 in 50 ml of pyridine at a temperature, stirring, 6.30 (0.0.6 mol) of cycloparopa carboxylic acid chloride are added dropwise, continue to be stirred for 1 / 2

h at room temperature, then poured onto 200 g of a mixture of water with a tid and mix well. After suctioning, rinse thoroughly with water and dry in an oven.

Output 10.25 g. (70%. Of theory), so pl. 10 4 C.

Similar compounds are obtained in table. one.

Table 1

The invention is illustrated by the following examples.

EXAMPLE 2. The test for the maximum concentration in the case of the struggle with Pythium ultimum.

20% powdered compositions of biologically active substances are uniformly mixed with soil heavily contaminated with Pythium ultimum. The clay soil containing 0.5 l of soil is filled with treated soil and

without aging 20 grains of Wunder von Kelvedon brain-grade pea are sown in each cup. After cultivation for 3 weeks at 20-24 ° C, the number of healthy pea plants is determined and the roots are scored.

Biologically active substances, consumption rates and results are given in table. 2

0

table 2

№ 1

Number 3

 five

№ 8

5-Ethoxy-3-trichloromethyl

1,2,4-thiadiazole (known)

Test experience (3 replicates)

contaminated soil Test experience (3 replicates)

steamed soils) Scale assessment of roots;

White roots, without fungal necrosis 4 White roots, slight fungal necrosis3

Brown roots, more fungal fungal necrosis2 Strong. Fungal necrosis, roots rotted

four

4 4 1 2 4 4 4 4 1 2 4 4 4 4

5 12

19 18 18

4 4 4

Example 3. The treatment of sugar beet.

Calibrated caxapHofi seed of the Dieckmai.n Syprapcly beetroot is pickled with 20% powder from a biologically active substance powder. Clay cups are filled with ordinary compost.

№ 1

 3

№ 4

 five

№ 8

5 Ethoxy-3 trichloromethyl-1, 2,4-thiadiazole (for comparison)

Tetramethylthiuramdisulphide (for comparison)

Control experiment G: (3 replicates) contaminated soil

Control experiment II: (3 replicates) steamed soil

PRI me R 4. Efficiency of prophylactic treatment of leaves against Plaswopara viticola on grape plants in a greenhouse.

Young plants of grapes from about 5 to 8 are sprayed with leaves, before collecting, with a preparation of the active substance at the concentration indicated in Table. 4. After spraying the coating as a result of spraying, the underside of the leaves is cut off with an aqueous suspension of fungal spores (approximately 20,000 per 1 ml) and immediately incubated in a greenhouse at 22–24 ° C and, if possible, in a saturated water vapor atmosphere. Starting from the second day, humidity

100 grains of sugar beet seeds are sown with earth and into each cup. After a cultivation period of 18 days at 9-2lc, healthy seedlings are determined in the greenhouse.

Biologically active substances, consumption rates and results are given in table. 3

table3

79 83 87 87 70 76 83 77 71 85

83 82

93

26

44 53

21 50

5 7 6

83 86 71

air for 3-4 days is brought to the norm (approximately 30-70% saturation), then next day it is kept at saturation with water vapor. Further, the percentage of the fungus surface damage of each leaf is estimated as a percentage and the average value of the fungicidal activity is calculated by the formula.

100 damage to treated plants

SO activity

Defeat untreated plants

The results are shown in Table. four.

Example 5. Prophylactic treatment of leaves against Phytophora infestans on tomato or potato plants in a greenhouse.

Young tomato plants with at least two developed leaves or potato plants (for example, developed from the eyes) with a height of at least 10 cm are sprayed before the active substances at a concentration specified in

Compound

No

ft

Ethylene bisdithioEthylene bisdithiocarbamate manganese (known, for comparison)

Activity against 100% damage in the case of untreated control plants,

Table

TOO

0.001

tab. 5. After drying, as a result of spraying, the leaves are sprayed with an aqueous suspension containing 50,000 - 80,000 fungal spores in 1 ml and incubated for about 2 hours in a refrigerator at. Fungi are incubated at high humidity and at about 15-18 0 in the greenhouse. After about 5 days, the percentage of affected leaf surface is estimated as a percentage. The results are shown in Table. -5 and 6. Table 5

Activity (%) of Phytophora infestans on potatoes with active substance concentration of 0.005%

95 VO

67

Example 6. Systemic action in tillage against Phytophotra infestans on tomato or potato plants in a greenhouse.

A certain amount of the substance is mixed into the arable land, flower pots are filled in with these plants, and young tomato plants are planted with at least two developed leaves or potato plants (for example, from eyes) with a height of at least 10 cm.

№ 4

X) Active against a 100% lesion in the case. untreated control plants.

EXAMPLE 7: Curative Effect in Treating Leaves Against Phycophora infestahs on Tomatoes or Potatoes.

Young tomato plants with at least two developed leaves or potato plants (for example, from eyes) with a height of at least 10 cm are sprayed with an aqueous solution containing 50,000 to 80,000 fungal spores in 1 ml and incubated for about 2 hours in a refrigerator with

Compound

before inoculation

No. 1, 100

No. 4100

Manganese ethylenebisdithiocarbamate91

Example 8. Action in the treatment of seeds n chg.1en against Helmithos-porium spec.

Barley seeds, affected by Helmi-tosporium spec, are treated with 50 mg of the biologically active substance per 100 g of seeds. Seeds are sown at a predetermined aging time (for example, 4 or 18 days later), spray plants {from water containing 50000-80000 fungal spores in 1 ml and inoculated for about 2 hours in a refrigerator at suspensions. The plants are incubated at high air humidity and at a temperature of about 15-18 ° C in a greenhouse. After about 5 days, the percentage of affected leaf surface is estimated as a percentage.

The results are shown in Table. 7

Table

82 71

25 5

92 40

suspension. Plants are incubated with high airflow. After a certain time, the plants are sprayed, during the time of hidden fungal infection, a test fungicide at a concentration of 0.004% before collecting. After the start of fungal infection in untreated control plants, the percentage of diseased leaf surface is estimated.

The results are in Table. eight.

Table 8 Activity%

1 day after inoculation

68 60

ABOUT

You and incubated in the climate chamber at. The test is evaluated after 6 weeks, and the seeds are affected much less compared to untreated plants of the control group. :

The results are shown in Table. 9.

(untreated control)

ABOUT

PRI me R 9. The test for maximum concentration in the case of Pythium ultimum.

Example 10. Prophylactic treatment of tomato seedlings against: Botrytis cinerea.

Young tomato plants are sprayed with a biologically active substance at a concentration of 0.06% in a droplet manner, dried, then treated

The 20% powdered drug of biologically active substances is uniformly mixed with the soil heavily contaminated with Pythium ultimum. Clay cups are filled with the treated soil. nor, containing 0.5 liters of soil and without aging, 20 grains of cereal pea Pisum sativum L, convar medullare Alef varieties Wender von Kelkedon are sown in each cup. After cultivation for 3 weeks at

20-24 C, the number of healthy pea plants is determined and the roots are estimated (as in Example 2).

Biologically active substances, consumption rates and results are presented in Table D. ten.

Table 10

and untreated plants are inoculated by spraying with a spur suspension (approximately 1 million for every 1 ml of fruit juice solution) of the botrytis cinerea botanical gray mold pathogen and incubated moist at a temperature of 20 ° C in a greenhouse. After

untreated pacTetiHR diseases (10D% of diseases) determine the extent of infection of the treated plants. The results are shown in Table. eleven.

Table 11

N- {1 Methoxycarboni) -N- (furan-2) -carbonyl-2, b-dimethylaniline

17

Thus, the proposed compounds have a high fungicidal action.

Claims (2)

1. Melnikov N.N. and pesticide technologists, M., Himi, 1974, p. 353, 358. 2.Patent UK I 144881 cl. from 2 s, pub. 1976 (prototype).