RU2773310C1 - Insect-fungicidal composition with synergistic efficacy - Google Patents

Abstract

FIELD: agriculture.

SUBSTANCE: invention relates to agriculture. The insecticidal-fungicidal composition for treating seeds of agricultural crops includes a mixture of fungicides consisting of tebuconazole and pyraclostrobin, and an insecticide, while additionally containing the fungicide prochlorase and as an insecticide contains an insecticide from the class of neonicotinoids acetamiprid, thiamethoxam or imidacloprid. The insecticidal-fungicidal composition contains components at a synergistic ratio of insecticide : prochloraz : pyraclostrobin : tebuconazole equal to (2÷13):(2÷15):(0.2÷5.0):1, respectively.

EFFECT: proposed insecticidal-fungicidal composition has a synergistic efficacy, prolonged phytopathogenic activity, is suitable for both crop treatment and seed dressing, provides high seed germination.

1 cl, 9 tbl, 3 ex

Description

SUBSTANCE: invention relates to means for crop treatment and seed treatment, namely: to a preparation comprising a synergistically active mixture having fungicidal and insecticidal properties, where fungicides prochlorase, pyraclostrobin, tebuconazole and one insecticide from the class of neonicotinoids, acetamiprid, are used as active components in the composition. , or thiamethoxam, or imidacloprid.

The control of plant diseases caused by plant pathogenic fungi is extremely important in achieving high crop yields, as plant diseases can cause a significant reduction in productivity. Plant disease pathogens are difficult to control and can develop resistance to industrial fungicides. New effective combinations of active compounds are needed to best meet the specific requirements of plant disease control.

Pests of cultivated plants infect seed material during storage and after the seed material has been introduced into the soil, as well as during and immediately after plant germination. This phase is especially critical due to the high sensitivity of the root system and plant seedlings: even a small damage can lead to the death of the entire plant. Therefore, seed treatment with special compositions is used.

The combined use of the active ingredients of fungicides and insecticides increases the spectrum of action, increases the efficiency of treatment and reduces the likelihood of resistance to pathogens of various crops due to the simultaneous action of different mechanisms of fungal infection.

Prochloraz - N-propyl-N-[2-(2,4,6-trichlorophenoxy)ethyl]-1H-imidazole-1-carboxamide, belongs to the class of imidazoles, is a systemic fungicidal agent against a wide range of pathogens of fungal diseases of the following types on various crops: Pseudocercosporella, Pyrenophora, Rhynchosporium, Septoria, Erysiphe, Alternaria, Botrytis, Pyrenopeziza, Sclerotinia and others (The Pesticide Manual, 18th edition, BCPC, 2018). The biological action of prochlorase is based on the mechanism of ergosterol inhibition.

Tebuconazole - α-[2-(4-chlorophenyl) ethyl]-α-(1,1-dimethylethyl)-1H-1,2,4-triazole-1-ethanol, belongs to the class of triazoles. Tebuconazole is a systemic fungicidal agent against a wide range of pathogens of fungal diseases, in particular: Pyrenophora, Rhynchosporium, Septoria, Erysiphe graminis, Alternaria, Tilletia, Puccinia, Sphacelotheca, Ustilago, Cercospora, Podosphaera, Fusarium, Venturia, etc. (The Pesticide Manual , 18th ed., BCPC, 2018). It has an uplifting and therapeutic effect. It is an inhibitor of steroid demethylation in the biosynthesis of ergosterol. The fungicide is designed to combat various fungal diseases of cereals, legumes, horticultural, vegetable and many other crops.

Pyraclostrobin - [Methyl N-{2-[1-(4-chlorophenyl)-1H-pyrazol-3-yloxymethyl] phenyl} (N-methoxy) carbamate, a fungicide from the class of contact and deep-acting strobilurins. Pyraclostrobin inhibits pathogen respiration. Focuses on the surface of the leaf, then gradually redistributed to the internal tissues. Preparations based on pyraclostrobin are used against diseases of corn (fusarium, blister smut, root and stem rot, helminthoriasis), soybean (peronosporosis, ascochitosis), etc. (List of pesticides and agrochemicals permitted for use on the territory of the Russian Federation, 2019). It is also known that the strobilurin fungicide pyraclostrobin can be used as a fungicide to control fungal plant diseases. Pyraclostrobin is described, for example, in "The Pesticide Manual", 13th ed. (2003), published by the British Crop Protection Council, or also in WO 96/01256 A1.

The mixture of the proposed composition of fungicides additionally contains an insecticide from the class of neonicotinoids, namely: acetamiprid, or thiamethoxam, or imidacloprid.

Acetamiprid - [N1-methyl-N1-[(6-chloro-3-pyridyl)methyl]-N2-cyanoacetamidine], belongs to the class of neonicotinoids, used in agriculture to control harmful insects. The active substance blocks nicotine-dependent acetylcholine receptors in the nervous system, namely, it disrupts the transmission of a nerve impulse through the synapse, and the insect dies from severe nervous overexcitation. Preparations based on acetamiprid are used against pests of wheat (bug bug, grain beetle), wheat and barley (corn beetle, cereal flies, striped bread flea), etc. The effectiveness of acetamiprid is high, but in relation to individual pests and in some cases does not respond high requirements for insecticides.

Thiamethoxam , 5-methyl-3-(2-chlorothiazol-5-ylmethyl)-1,3,5-oxadiazinan-4-ylidene-N-nitroamine, C8H10ClN5O3S insecticide from the neonicotinoids class. Insecticide of systemic and contact-intestinal action with translaminar activity (absorbed into the vascular system of plants and spreads through it, making them poisonous to insects), suppresses piercing-sucking and gnawing agricultural pests, including secretive-living and feeding on the lower part of the leaf.

Imidacloprid (4,5-dihydro-N-nitro-1-[(6-chloro-3-pyridyl)-methyl]-imidazolidin-2-ylene-amine), C9H10ClN5O2, is the most widely used neonicotinoid insecticide. Imidacloprid has a pronounced systemic effect: it penetrates the vascular system of plants, and the plant becomes toxic to insects.

Based on the patent search, the following patents were selected related to the fungicides and insecticides listed above.

Pyraclostrobin is used in fungicidal compositions in combination with other active compounds, often in synergistically effective amounts. For example, with pyridylethylbenzamide derivatives (RF No. 2360417), with an amide derivative of a carboxylic acid (RF No. 2483541), with a 1,2,3-thiadiazole derivative (RF No. 2165144), with N-sulfonylvalinamide (RF No. 2270564), and other compounds having fungicidal activity (RF No. 2417590, 2547554).

To expand the spectrum of action and enhance biological activity, tebuconazole is used in various mixed preparations (US Pat. RF No. 2024228, 2040899, 2232504, 2483541, 2192743).

Known fungicidal composition (RU No. 2672493), including fungicides prochloraz, strobiluric fungicide azoxystrobin, prothioconazole, insecticide acetamiprid and auxiliary components. Used for seed treatment. The disadvantage of this composition is the low efficiency of the drug.

Also known is a fungicidal composition for plant protection (WO2009098210), which includes as active components an insecticidal compound selected from the series: acetamiprid, fungicidal compounds prochlorase and pyraclostrobin.

Known fungicidal composition for pre-sowing treatment of wheat seeds (RU2656965), including active ingredients tebuconazole and prochloraz, auxiliary components and additionally includes strobilurin fungicide kresoxim-methyl.

A two-component plant protection agent is known (EA No. 016724), which includes a synergistically active mixture of at least one substance selected from the group that includes (a) acetamiprid, with at least one substance selected from the group that includes (b) pyraclostrobin. Can be used as a fungicide prochloraz or tebuconazole. This seed treatment agent is used to control pests and diseases that affect plants or seed material.

The closest technical solution to the claimed composition is a two-component mixture comprising component (a), which is a fungicide from the pyrazole derivative class; component (b) comprises at least one fungicide selected from two different groups, pyraclostrobin, tebuconazole, prochloraz. The composition is used to protect a plant or plant seeds from diseases caused by pathogenic fungi. The composition may contain as (b) at least one agent for the control of invertebrate pests, such as acetamiprid or thiamethoxam or imidacloprid (RF patent No. 2572202).

The disadvantage of the known compositions is that they do not provide complete control over the diseases of cultivated plants or require increased consumption rates during processing.

The objective of the invention is to expand the range of active insecticidal-fungicidal compositions for plant protection. Specifically, for seed treatment in order to control disease at an early stage of growth, which will reduce the environmental burden by minimizing the doses of chemicals while maintaining the high efficiency of protective treatments. Also, the technical objective of this invention is to preserve the seed from spoilage while maintaining high germination of the seed and growth in the initial period of vegetation.

The technical result is the creation of a composition with synergistic efficiency, with prolonged phytopathogenic activity and high seed germination. The composition exhibits greater biological efficiency at lower consumption rates of the active ingredients included in the composition. At the same time, due to the use of active substances with different biological mechanisms of action, the risk of resistance in pathogenic organisms is reduced. Due to this, there is no need for additional processing of the crop during sowing or after a short period after it.

The technical result is achieved through the use of an insecticidal-fungicidal composition for the treatment of crops, including a mixture of fungicides, consisting of tebuconazole and pyraclostrobin, and an insecticide. At the same time, the composition additionally contains the fungicide prochloraz and, as an insecticide, a neonicotinoid, mainly acetamiprid, with a synergistic ratio of components in the composition, acetamiprid : prochloraz : pyraclostrobin : tebuconazole equal to (2 ÷ 13) : (2 ÷ 15) : (0.2 ÷ 5), respectively ,0) : 1.

In addition, in the insecticidal-fungicidal composition, thiamethoxam or imidacloprid is used as a neonicotinoid insecticide.

The insecticidal-fungicidal agent according to the present invention retains its original physical and chemical properties and biological activity under standard storage conditions for a long period of time.

The efficiency of the known compounds is high, however, at small consumption amounts and in relation to individual pathogens, in some cases it does not meet the high requirements for fungicides. Therefore, fungicides are often combined in a mixture to expand the spectrum of fungicidal activity, to achieve a synergistic effect, and in order to delay pathogen resistance to one of the components of the mixture.

The high fungicidal efficacy of this composition is evident from the examples below.

Example 1. Laboratory tests. Determination of the fungicidal synergistic effect (see tables 1-3)

Experimental procedure: An experimental study of the fungicidal and fungistatic activity of the samples was carried out by the method of agar cuttings. For analysis, working solutions of samples were prepared with a concentration that was determined by the field rate of consumption of active substances, taking into account the rate of consumption of the working fluid. To obtain comparative data and exclude the achievement of maximum efficiency, the consumption rate was reduced by 5 times. Then, 180 μl of the working solution of the fungicidal disinfectant was dropped into sterile Petri dishes (the consumption rates per 1 ton of seeds were recalculated for the surface area of the Petri dish with a diameter of 87 mm), poured into the KSA nutrient medium pre-sterilized and cooled to 45°C, and stirred until completely mixed. medium and drug. After the agar solidified, blocks of mushrooms 1 cm in diameter, cut out with a sterile punch, were placed in the center of each dish. The repetition of experience 3-fold. Thermostated at a temperature of 8-25°C for 7-20 days (depending on the growth rate of fungi), after which the presence or absence of mycelial growth zones around the agar blocks was recorded and compared with the control.

The growth rate of fungi was calculated as the ratio of the diameter of mycelium growth in the experimental variant to the control, expressed in %.

The biological activity of active substances and mixtures thereof was calculated according to the following formula: 100% - (growth rate).

Repetition - 4-fold.

The expected efficiency is calculated using the Colby formula

E _expected.

where:

X and Y are observed efficacy for individually applied fungicides at the indicated dose in g/ha or g/t;

E _expect - the expected result for a mixture of fungicides;

E _exp - the result obtained as a result of the experiment.

If the ratio between the experimentally observed efficiency (E _exp. ) and the expected efficiency (E _expect ) - synergistic factor (SF) - is more than 1, the mixture exhibits a synergistic effect

This synergistic effect guarantees increased reliability in the fight against crop diseases, leading to a significant reduction in the amount of active ingredient required to achieve the same biological effect, or maintaining the rate of consumption of the active substance while increasing biological efficiency. The results are presented in tables 1-3

Example 2 Laboratory tests. Determination of the insecticidal synergistic effect (see Tables 4-6)

Wheat seeds are treated with the agent in accordance with the norms indicated in table 4. Wireworm larvae (fam. Elateridae) are planted on the treated seeds, after 3 days the mortality of larvae, expressed as a percentage, is determined. It is believed that 100% means that all larvae are dead, 0% - all larvae are alive.

Synergy is calculated using the Colby formula

E _expected.

where

X - death of larvae in %, calculated in relation to the untreated control, (active substance A);

Y - the death of larvae in%, calculated in relation to the untreated control, (group of active substances B);

E _expected. - expected death of larvae in % in relation to the untreated control when using a synergistic mixture of substances A + B in the indicated ratios.

If the ratio between the experimentally observed efficiency (E exp.) and the expected efficiency (E expect) - synergistic factor (SF) - is more than 1, the mixture exhibits a synergistic effect:

See Tables 4-6 for synergistic coefficients of insecticidal mixtures in seed treatment.

Example 3. Field small-plot tests (see tables 8-9)

The effectiveness of the claimed composition was studied in the field when processing seeds of cereals. Method of application - seed treatment Test results are given in the tables 8-9

The proposed mixture (150 g/l acetamiprid + 100 g/l prochlorase + 20 g/l tebuconazole + 15 g/l pyraclostrobin) was tested on spring and winter wheat, spring and winter barley against diseases: hard loose smut, fusarium, helminthosporium and rhizoctonia root rot, septoria, seed mold, powdery mildew, cercosporella rot, root neck, pithy root rot, snow mold; against pests: grass fly, wireworm, bread flea, aphids, leech, leafhopper, grain beetle. Presowing treatment of these crops was carried out.

The resulting composition, along with a protective effect against a wide range of pests and diseases, has a pronounced positive effect on the germination of seed material and further plant growth.

To account for phytotoxicity, laboratory seed germination was determined, which was expressed as a percentage, the data were processed statistically. The laboratory germination of seeds was determined according to GOST 12038-84. - 07/01/86. Seeds of agricultural crops. Germination methods. When taking into account germination, normally germinated seeds were counted. The result of the analysis was taken as the arithmetic mean of the results of determining the germination of all analyzed samples (table 7).

Table 1. Efficacy of active ingredient mixtures for the control of Bipolavis sorokiniana (Helminthosporium root rot)

Active ingredients Dose, g AI/t The ratio of AI Prochloraz: Tebuconazole: Pyraclostrobin E _exp. E _expected. SF one Prochloraz
Tebuconazole 150
thirty 52.1 pyraclostrobin 22.5 22.4 Prochloraz
Tebuconazole
pyraclostrobin 150
thirty
22.5 5:1:0.75 73.5 62.8 1.17 2 Prochloraz
Tebuconazole 150
ten 44.6 pyraclostrobin 2 11.5 Prochloraz
Tebuconazole
pyraclostrobin 150
ten
2 15:1:0.2 55.1 51.0 1.08 3 Prochloraz
Tebuconazole 40
twenty 21.2 pyraclostrobin 100 68.1 Prochloraz
Tebuconazole
pyraclostrobin 40
twenty
100 2:1:5 80.6 74.9 1.08

Table 2. Efficacy of active ingredient mixtures for the control of Fusarium Oxysporum (Fusarium root rot)

Active ingredients Dose, g AI/t AI ratio (Prochloraz:Tebuconazole:Pyraclostrobin) E _exp. E _expected. SF one Prochloraz
Tebuconazole 150
thirty 54.3 pyraclostrobin 22.5 26.1 Prochloraz
Tebuconazole
pyraclostrobin 150
thirty
22.5 5:1:0.75 76.2 66.2 1.15 2 Prochloraz
Tebuconazole 150
ten 50.8 pyraclostrobin 2 12.2 Prochloraz
Tebuconazole
pyraclostrobin 150
ten
2 15:1:0.2 63.0 56.8 1.11 3 Prochloraz
Tebuconazole 40
twenty 26.7 pyraclostrobin 100 52.1 Prochloraz
Tebuconazole
pyraclostrobin 40
twenty
100 2:1:5 68.1 64.9 1.05

Table 3 Efficacy of active ingredient mixtures for the control of Microdochium nivale (snow mold)

Active ingredients Dose, g AI/t AI ratio (Prochloraz:Tebuconazole:Pyraclostrobin) E _exp. E _expected. SF one Prochloraz
Tebuconazole 150
thirty 71.2 pyraclostrobin 22.5 14.8 Prochloraz
Tebuconazole
pyraclostrobin 150
thirty
22.5 5:1:0.75 89.0 75.5 1.18 2 Prochloraz
Tebuconazole 150
ten 70.5 pyraclostrobin 2 8.8 Prochloraz
Tebuconazole
pyraclostrobin 150
ten
2 15:1:0.2 80.5 73.1 1.10 3 Prochloraz
Tebuconazole 40
twenty 38.4 Pyraclostrobin 100 32.7 Prochloraz
Tebuconazole
pyraclostrobin 40
twenty
100 2:1:5 64.0 58.5 1.09

Table 4. Determination of insecticidal synergistic effect (acetamiprid)

Active ingredients Dose, g AI/t DV ratio E _exp. E _expected. SSF one BUT Acetamiprid 225 83.3 AT Prochloraz
Tebuconazole
pyraclostrobin 150
thirty
22.5 6.7 Acetamiprid
Prochloraz
Tebuconazole
pyraclostrobin 225
150
thirty
22.5 7.5:5:1:0.75 90.0 84.4 1.07 2 BUT Acetamiprid 60 40.0 AT Prochloraz
Tebuconazole
pyraclostrobin 150
thirty
22.5 0 Acetamiprid
Prochloraz
Tebuconazole
pyraclostrobin 225
150
thirty
22.5 2:5:1:0.75 50.0 40.0 1.25 3 BUT Acetamiprid 390 90.0 AT Prochloraz
Tebuconazole
pyraclostrobin 150
thirty
22.5 3.3 Acetamiprid
Prochloraz
Tebuconazole
pyraclostrobin 225
150
thirty
22.5 13:5:1:0.75 96.7 90.33 1.07

Table 5. Determination of the insecticidal synergistic effect (thiamethoxam)

Active ingredients Dose, g AI/t DV ratio E _exp. E _expected. SSF one BUT Thiamethoxam 225 80.0 AT Prochloraz
Tebuconazole
pyraclostrobin 150
thirty
22.5 3.3 Thiamethoxam
Prochloraz
Tebuconazole
pyraclostrobin 225
150
thirty
22.5 7.5:5:1:0.75 83.3 80.7 1.03 2 BUT Thiamethoxam 60 43.3 AT Prochloraz
Tebuconazole
pyraclostrobin 150
thirty
22.5 3.3 Thiamethoxam
Prochloraz
Tebuconazole
pyraclostrobin 225
150
thirty
22.5 2:5:1:0.75 53.3 45.2 1.18 3 BUT Thiamethoxam 390 83.3 AT Prochloraz
Tebuconazole
pyraclostrobin 150
thirty
22.5 0 Thiamethoxam
Prochloraz
Tebuconazole
pyraclostrobin 225
150
thirty
22.5 13:5:1:0.75 90.0 83.3 1.08

Table 6. Determination of insecticidal synergy (imidacloprid)

Active ingredients Dose, g AI/t DV ratio E _exp. E _expected. SSF one BUT Imidacloprid 225 86.6 AT Prochloraz
Tebuconazole
pyraclostrobin 150
thirty
22.5 0 Imidacloprid
Prochloraz
Tebuconazole
Pyraclostrobin 225
150
thirty
22.5 7.5:5:1:0.75 90.0 86.6 1.04 2 BUT Imidacloprid 60 40.0 AT Prochloraz
Tebuconazole
pyraclostrobin 150
thirty
22.5 10.0 Imidacloprid
Prochloraz
Tebuconazole
pyraclostrobin 225
150
thirty
22.5 2:5:1:0.75 50.0 46.0 1.09 3 BUT Imidacloprid 390 96.6 AT Prochloraz
Tebuconazole
pyraclostrobin 150
thirty
22.5 0 Imidacloprid
Prochloraz
Tebuconazole
pyraclostrobin 225
150
thirty
22.5 13:5:1:0.75 100 96.6 1.04

Table 7. Determination of laboratory germination of seeds of spring barley

Experience variant The rate of application of the drug,
l/t seed germination energy,
% laboratory germination
seed,
% 150 g/l acetamiprid + 100 g/l prochlorase + 20 g/l tebuconazole + 15 g/l pyraclostrobin 1.2 93.5 97.5 150 g/l acetamiprid + 100 g/l prochlorase + 20 g/l tebuconazole + 15 g/l pyraclostrobin 1.5 93.0 97.0 Control (no processing) - 88.5 92.5

Table 8. The effectiveness of the agent against the complex of seed and soil infection of spring barley (variety Nutans 642) in the conditions of the Volgograd region

Experience variant Norm
applications
funds
l/t Field
germination
seed,
% Density
standing
plants,
pcs/m ² B I P O S O + F U S A S P DRECTE USTINU USTIHO tillering education
2nd node develop-
tie,
% effect-
tiv-
ness,
% develop-
tie,
% effect-
tiv-
ness,
% develop-
tie,
% effect-
tiv-
ness,
% hit-
nie,
% effect-
tiv-
ness,
% hit-
nie,
% effect-
tiv-
ness,
% 150 g/l acetamiprid + 100 g/l prochlorase + 20 g/l tebuconazole + 15 g/l pyraclostrobin 1.2 92.2 328 3.7 60.6 11.4 39.0 3.8 28.3 0.0 100 0.0 100 150 g/l acetamiprid + 100 g/l prochlorase + 20 g/l tebuconazole + 15 g/l pyraclostrobin 1.5 92.5 329 2.6 72.3 9.9 47.1 3.3 360.2 0.0 100 0.0 100 Control (no processing) - 86.5 309 9.4 - 18.7 - 8.3 - 1.35 - 4.05 -

Note: BIPOSO + FUSASP - Bipolaris sorokiniana + Fusarium spp. (helminthosporium-fusarium root rot)

DRECTE - Drechslera teres (net spot)

USTINU - Ustilago nuda (dusty smut)

USTIHO - Ustilago hordei (hard (stone) smut)

Table 9. Biological effectiveness of the product in the fight against wheat fly (Phorbia fumigata Meigen) on spring barley (variety Nutans 642) in the conditions of the Volgograd region

Option
experience Norm
expense
drug, l/t repetition The average number of larvae per linear m row after germination by days of accounting Decrease in the number of the pest relative to the control after the emergence of seedlings per day of counting, % Biological grain harvest,
c/ha 12 19 26 12 19 26 150 g/l acetamiprid + 100 g/l prochlorase + 20 g/l tebuconazole + 15 g/l pyraclostrobin 1.2 one 0 0 0 100 100 100 32.8 2 0 0 0 100 100 100 32.4 3 0 0 0 100 100 100 32.6 four 0 0 0 100 100 100 33.1 cf. 0 0 0 100 100 100 32.7 150 g/l acetamiprid + 100 g/l prochlorase + 20 g/l tebuconazole + 15 g/l pyraclostrobin 1.5 one 0 0 0 100 100 100 32.7 2 0 0 0 100 100 100 33.3 3 0 0 0 100 100 100 32.4 four 0 0 0 100 100 100 32.9 cf. 0 0 0 100 100 100 32.8 Control - one 12.5 11.5 11.0 − − − 22.4 2 11.5 10.5 10.0 − − − 21.7 3 13.5 12.5 11.5 − − − 22.8 four 13.5 12.0 10.5 − − − 21.9 cf. 12.8 11.6 10.8 − − − 22.2

Claims (1)

Insecticidal-fungicidal composition for seed treatment of agricultural crops, including a mixture of fungicides, consisting of tebuconazole and pyraclostrobin, and an insecticide, characterized in that the composition additionally contains the fungicide prochlorase and as an insecticide contains an insecticide from the class of neonicotinoids acetamiprid, thiamethoxam or imidacloprid in a synergistic ratio of components in the composition insecticide : prochloraz : pyraclostrobin : tebuconazole, equal to (2÷13):(2÷15):(0.2÷5.0):1, respectively.