WO2023102761A1

WO2023102761A1 - Fungicidal composition containing picolinamide compound, and method for controlling plant pathogenic fungi

Info

Publication number: WO2023102761A1
Application number: PCT/CN2021/136284
Authority: WO
Inventors: 罗昌炎; 布里斯托詹姆斯·蒂莫西
Original assignee: 江苏龙灯化学有限公司
Priority date: 2021-12-08
Filing date: 2021-12-08
Publication date: 2023-06-15
Also published as: CN116916752A

Abstract

The present invention relates to a fungicidal composition containing a picolinamide compound. The fungicidal composition comprises an active ingredient compound (I) and oxathiapiprolin, the weight ratio of the compound I to the oxathiapiprolin being 50:1-1:25. The present invention further provides a method for preventing or controlling attacks of plant pathogenic fungi on plants, plant parts, plant propagation materials and subsequently grown plant organs.

Description

A kind of fungicidal composition comprising pyridine amide compound and method for controlling plant pathogenic bacteria

technical field

The invention relates to a fungicidal composition containing pyridine amide compounds and also relates to a method for controlling plant pathogenic bacteria.

Background technique

Fungicides containing a single active ingredient often have certain defects in the prevention and control of agricultural diseases. Continuous repeated use not only makes pathogenic bacteria easy to develop drug resistance, but also easily causes pollution to food and the environment. Improved activity against phytopathogenic fungi at a reduced total amount of active compound applied can be provided by judicious mixing of fungicide active ingredients in order to reduce the application rate of known active compounds and to improve their activity spectrum. Thereby, the pollution of food and environment by pesticides can be reduced or even avoided.

Compound I is known from WO2016109257A1, which belongs to pyridine amides. Compound I can protect plants or seeds from the attack of phytopathogenic fungi such as Ascomycetes, Basidiomycetes, Deuteromycetes and Oomycetes.

Owing to the continuously increasing environmental and economic demands placed on fungicides today, such as requirements on activity spectrum, toxicity, selectivity, application rate, residue composition and favorable manufacturing feasibility, and also due to the possible presence, for example, of drug resistance question. Therefore, it is the subject of continuous research to provide fungicidal compositions that are safer, have better performance, are applied at lower doses, are easier to use and cost less.

Contents of the invention

We have found that simultaneous, ie joint or separate application of compound I and fluthiapiprofen, or sequential application of compound I and fluthiapiprofen, results in better control of phytopathogens than application of the individual compounds alone.

It is therefore an object of the present invention to provide a fungicidal composition comprising pyridine amides, wherein compound I and fluthiapiprofen are present in the composition in an amount that produces a synergistic effect. When the weight ratio of compound I and thiazolidinone is 50:1-1:25, preferably 25:1-1:25, more preferably 20:1-1:20, more preferably 20:1- 1:10, more preferably 10:1-1:10, more preferably 10:1-1:5, more preferably 10:1-1:2, the synergistic effect is more obvious.

Synergistic effect refers to when the effect of the combination of active ingredients exceeds the sum of the effects of the individual components. For a given combination of active ingredients, the expected effect E can be calculated using the so-called "Colby's formula" (see S.R. Colby, "Calculating Synergistic and Antagonistic Responses of Herbicide Combinations", Weeds 1967, 15, 20-22) as follows: if

X is the activity when using active compound A in mg/ha or mppm concentration;

Y is the activity when active compound B is used at a rate of ng/ha or at a concentration of n ppm, expressed as a percentage of the untreated control;

E is the activity when using active compounds A and B in m and n g/ha or m and nppm concentrations,

So

A synergistic effect exists if the actually observed activity (O) is greater than the expected activity (E).

The synergistic activity produced by compound I and fluthiapiprofen allows on the one hand to reduce the application rate of compound I and fluthiapiprofen while the control effect remains equally good, which means that even in such a low application rate range , the composition still achieves a high degree of phytopathogen control where the two individual components have become overall ineffective; on the other hand, allows a substantial broadening of the spectrum of phytopathogens that can be controlled.

The fungicidal composition containing pyridine amide compounds of the present invention can be used as a foliar treatment agent in crop protection, and can also be used for seed dressing and soil treatment agent. The fungicidal composition according to the invention can be applied before or after the cultivated plants are infected.

Another aspect of the present invention is to provide a method for preventing or controlling phytopathogenic bacteria from infecting cultivated plants, comprising applying the fungicidal composition of the present invention comprising pyridine amide compounds to phytopathogenic bacteria and/or their environment, or in plants, plant propagation material and subsequently grown plant organs, soil or growing medium, material or space.

The present invention provides a method for preventing or controlling phytopathogenic bacteria from infesting cultivated plants, the method comprising applying the fungicidal composition of the present invention in the form of seed treatment, foliage application, stem application at an agronomically effective and substantially non-phytotoxic application rate. , drenching, dripping, pouring, spraying, spraying, dusting, spreading or fuming and other methods to apply to phytopathogens and/or their environment.

The fungicidal composition comprising the pyridine amide compounds of the present invention is particularly effective against the following plant diseases: wheat brown rust (Puccinia striiformis); wheat stripe rust (Puccinia striiformis); wheat spot blight (Puccinia graminearum ( Mycosphaerella graminicola); Septoria tritici); Glume blotch of wheat (Leptosphaeria nodorum): Stagonospora nodorum); Cochliobolus sativum); wheat root rot (Helminthosporium sativum); sugar beet brown spot (Cercospora beticola); fungus (Mycosphaerella arachidis); Cercospora arachidicola; cucumber anthracnose (Colletotrichum Iagenarium); Mycosphaerella fijiensis)); white mold (Sclerotinia sclerotiorum); apple scab (Venturia inaequalis; grape powdery mildew (Erysiphe necator)); barley scald (Barley cloud Rhynchosporium secalis)); rice blast (Pyricularia oryzae)); soybean rust (Phakopsora pachyrhizi)); wheat powdery mildew (Blumeria graminis f.sp. tritici)); Powdery mildew (Erysiphe cichoracearum); tomato early blight (Alternaria solani); watermelon blight (Didymella bryoniae); apple powdery mildew (Podosphaera leucotricha ); gray mold (Botrytis cinerea); sclerotinia white mold (Sclerotinia sclerotiorum); rice fever (Pyricularia oryzae); stone fruit brown rot (Peach brown rot Monilinia fructicola)); Cucumber downy mildew (Pseudoperonospora cubensis (Berk.et Curt.) Rostov.); Tomato late blight (Phytophthora infestans); Cucumber damping-off (Bythium deliense Meurs .).

Plants suitable for the present invention include: vines; cereals (such as wheat, barley, rye or oats); sugar beets (such as sugar beet or fodder beet); fruits (such as pome, stone fruit or berries, such as apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, or blackberries); leguminous plants (such as fava beans, lentils, peas, or soybeans); oil plants (such as canola, mustard, poppies, olives, sunflowers, coconuts, castor oil plants, cocoa beans or groundnuts); melons (such as baby gourds, cucumbers, or melons); fibrous plants (such as cotton, flax, hemp, or jute); citrus fruits (such as oranges, lemons, grapefruit, or tangerines); vegetables (such as spinach , lettuce, asparagus, cabbage, carrot, onion, tomato, potato, gourd or red pepper); Lauraceae (such as avocado, cinnamon or camphor); corn; tobacco; nuts; coffee; sugar cane; tea; vines; hops; Durian; banana; natural rubber tree; turf or ornamental plants (such as flowers, shrubs, broad-leaved trees or evergreens such as conifers).

The fungicidal compositions of the present invention comprising picolinamides can be used to protect plants, plant parts, plant propagation material and subsequently grown plant organs from attack by phytopathogenic fungi.

"Plant" refers to all plants and plant populations, such as desirable and undesirable wild plants, cultivated plants and plant varieties (whether or not protected by plant variety or plant breeder's rights). Cultivated plants and plant varieties may be plants obtained by conventional methods of propagation and breeding, which may be supplemented or complemented by one or more biotechnological methods, such as the use of double haploids, protoplast fusion, random and directed mutagenesis, molecular Or genetic markers, or using bioengineering and genetic engineering methods.

"Plant parts" means all above- and below-ground parts and organs of plants, such as buds, leaves, flowers and roots, such as leaves, needles, stems, branches, flowers, fruiting bodies, fruits and seeds as well as roots, bulbs and rhizomes. Crops and vegetative and generative propagation material, such as cuttings, bulbs, rhizomes, runners and seeds, also belong to plant parts.

"Plant propagation material" is understood to mean all reproductive-competent plant parts, such as seeds, which can be used to propagate the latter, as well as vegetable material such as cuttings or tubers (eg potatoes). Therefore, the used in this paper

"Plant parts" include plant propagation material. There may be mentioned, for example, seeds, roots, fruits, tubers, bulbs, rhizomes and plant parts. Germinated plants and effective plants to be inhibited after germination from soil or after emergence. Young plants can be protected by total or partial treatment by dipping before transplanting.

A "subsequently grown plant organ" is any part of a plant that is produced from plant propagation material, such as seeds. Plant parts, plant organs and plants can also benefit from the protection from pathogen damage obtained by applying the fungicidal composition to plant propagation material. Certain plant parts and plant organs grown after certain loci can also be considered as plant propagation material, which can itself be applied (or treated) with a fungicidal composition; Plants, other plant parts and other plant organs may also benefit from application of the fungicidal composition.

The fungicidal compositions of the present invention comprising pyridine amides can be used to protect seeds from soil harmful fungi and to protect the roots and shoots of the resulting plants from attack by soil harmful fungi. Preference is given to protecting the roots and shoots of the plants.

The present invention provides a method for protecting seeds, seedling roots and shoots from phytopathogenic fungi, comprising contacting the seeds with an effective amount of the fungicidal composition of the present invention before sowing and/or after germination. The seed is treated to protect the seed from attack by phytopathogenic fungi and to protect the resulting plant roots and shoots.

The seeds treated with the fungicidal composition containing pyridine amide compounds of the present invention provide protection not only for the seeds themselves but also for plants grown from the seeds from attack by pathogens after emergence. Thus, it may not be necessary to treat the plants directly at or shortly after sowing.

Described seed is selected from potato, sunflower, coffee, tobacco, canola, rape, sugar beet, tomato, cucumber, kidney bean, Brassica plant, onion, soybean, wheat, barley, rye, oat, sorghum, peanut, sugarcane , rice, cabbage, cowpea, carrot, cotton and corn seeds.

On the other hand, the present invention also provides a method for preventing and controlling soil harmful bacteria. The fungicidal composition containing pyridine amide compounds according to the present invention is applied to the soil and/or directly before germination, after germination or before and after germination. Apply to soil in contact with plant roots or to soil suitable for plant growth.

The fungicidal composition containing pyridine amide compounds of the present invention can be mainly in the form of a preparation, that is, the substances in the composition have been mixed, and the components of the composition can also be provided in a single dose form, mixed in a barrel or tank before use, and then diluted to the desired concentration. Among them, the preparation form provided by the present invention is preferred.

The fungicidal composition containing pyridine amide compounds of the present invention can be used in any conventional formulation. Such as emulsifiable concentrate, water suspension, oil suspension, seed treatment dry powder, seed treatment solution, seed treatment emulsion, suspension seed coating, water dispersible granule, wettable powder, suspoemulsion, granule, water emulsion, microcapsule suspension Agents, dry suspensions, ultra-low volume liquids, electrostatic oils, fine particles.

In the formulation form, the active ingredients are from 1% to 90% by weight, the agriculturally acceptable surfactant is from 0 to 20%, and the filler is from 10% to 99%.

According to the present invention, the term "extender" refers to a natural or synthetic organic or inorganic compound which can be combined or associated with an active compound to make it easier to apply to a subject such as a plant, crop or grass. Thus, the filler is preferably inert, at least agriculturally acceptable. The filler can be solid or liquid.

The inactive medium that can be used in the present invention can be solid also can be liquid, can use as solid medium material for example: talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, diatomaceous earth, limestone , calcium carbonate, bentonite, calcium montmorillonite, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, ground walnut shells, lignin and similar substances.

What can be used as a liquid vehicle material can be selected from the following materials, such as water, petroleum ether, vegetable oil, methyl ethyl ketone, cyclohexanone, amyl acetate, 2-butanone, butylene carbonate, cyclohexane, Cyclohexanol, alkyl acetate, diacetone alcohol, diethanolamine, diethylene glycol, diethylene glycol rosinate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N, N-Dimethylformamide, Dimethyl Sulfoxide, Dipropylene Glycol, Dipropylene Glycol Methyl Ether, Dipropylene Glycol Dibenzoate, Dipropylene Glycol, Alkylpyrrolidone, Ethyl Acetate, 2-Ethylhexanol , ethylene carbonate, 2-heptanone, ethyl lactate, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, γ-butyrolactone, glycerol, glyceryl acetate, glyceryl diacetate , glyceryl triacetate, hexadecane, hexanediol, isoamyl acetate, isobornyl acetate, isooctane, isophorone, isopropyl myristate, lactic acid, laurylamine, isopropylidene Propyl acetone, methoxy propanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl caprylate, methyl oleate, n-hexane, n-octylamine, octadecanoic acid, octadecanoic acid Amine acetate, oleic acid, oleylamine, polyethylene glycol, propionic acid, propyl lactate, propylene carbonate, propylene glycol, propylene glycol methyl ether, triethyl phosphate, triethylene glycol, paraffin, mineral Oil, ethyl acetate, amyl acetate, butyl acetate, propylene glycol methyl ether, diethylene glycol methyl ether, ethanol, isopropanol and higher molecular weight alcohols such as amyl alcohol, tetrahydrofuran alcohol, hexanol, octanol Alcohol, ethylene glycol, propylene glycol, glycerin, N-methyl-2-pyrrolidone, etc.

Suitable surfactants include, for example, fatty alcohol polyoxyethylene ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylene higher fatty acid esters, polyoxyethylene alcohol or phenol phosphate esters, polyol fatty acid esters, alkanes Aryl sulfonic acid, naphthalene sulfonic acid polymer, lignin sulfonate, polymer comb-shaped branched copolymer, butyl naphthalene sulfonate, alkylaryl sulfonate, sodium alkyl sulfosuccinate, oil , Fatty alcohol and ethylene oxide condensate, alkyl taurate and other polyacrylates, protein hydrolyzate. Suitable oligosaccharides or polymers are eg based on vinylic monomers, acrylic acid, polyoxyethylene and/or polyoxypropylene alone or in combination with eg (poly)alcohols or (poly)amines.

For dispersion stabilization, adhesion and/or binding of active ingredient compounds, for example, xanthan gum, magnesium aluminum silicate, gelatin, starch, cellulose methyl ether, polyvinyl alcohol, polyvinyl acetate and natural phospholipids and synthetic phospholipids can be used , bentonite, sodium lignosulfonate and other auxiliary agents.

Among them, the antifreeze can be selected from ethylene glycol, propylene glycol, glycerol, and sorbitol. As the deflocculating agent for suspension products, auxiliary agents such as naphthalenesulfonic acid polymers and polymeric phosphates can be used.

Silicone defoamers can be used as defoamers.

Colorants that can be used, such as inorganic pigments such as iron oxide, titanium oxide and Prussian blue; and organic pigments/dyes: alizarin dyes, azo dyes and metal phthalocyanine dyes; and trace elements such as iron salts, manganese salts, Salts of boron, copper, cobalt, molybdenum and zinc.

Optionally, other additional components can also be included, such as protective colloids, adhesives, thickeners, thixotropes, penetrants, stabilizers, masking agents.

Compound I and fluthiapiprofen of the present invention can also be administered in combination with other active ingredients, for example to broaden the spectrum of activity or prevent the development of resistance. The other active ingredients are, for example, fungicides, bactericides, attractants, insecticides, acaricides, nematicides, growth regulators, herbicides, safeners, fertilizers or semiochemicals.

Detailed ways

biological test case

The following biological test examples are used to illustrate the present invention. However, the present invention is not limited to these Examples.

Trial 1: Tomato Late Blight

Dissolve compound I and the original drug of fluthiapiprofen in acetone to prepare a single-dose mother solution, and then dilute to the required concentration with an aqueous solution containing 0.1% Tween-80.

The fungicidal activity of pesticides against tomato late blight was determined by living pot method. Tomato seedlings are planted in plastic pots, and the substrate is vegetable planting substrate. Pot culture until 2-4 true leaves stage for later use.

Cultivate the pathogenic bacteria used in the test on a suitable medium. After the sporangia are produced, rinse the sporangia with distilled water at 4°C, filter with double-layer gauze to make a sporangium suspension, place it at a low temperature at 4°C, and treat it in the dark for 0.5 -3h, make it release zoospores, and adjust the concentration of spores at 1×10 ⁵ /mL for later use.

Stems and leaves were evenly sprayed on the potted seedlings for testing. The front and back sides of the leaves to be inoculated were sprayed with each treatment agent until moist, and inoculated 24 hours later. 3 pots per treatment, 4 repetitions. And the treatment without medicament (containing organic solvent and emulsifier) was set as blank control.

Spray the sporangia suspension evenly on the back of tomato leaves with an inoculation sprayer. After inoculation, the tomato seedlings were alternately lighted/dark every day for 12 hours, the light intensity was 10000Lux, the temperature was 18°C-20°C, and the water film was kept on the leaves within 24 hours after inoculation, and the relative humidity was more than 90% for 7 days.

When the rate of diseased leaves in the blank control reached more than 50%, the disease incidence of each treatment was investigated step by step. At least 30 leaves were investigated for each treatment;

The grading method is:

Grade 0: no lesions;

Grade 1: Lesion area accounts for less than 10% of the entire leaf area;

Grade 3: Lesion area accounts for 10%-25% of the entire leaf area;

Grade 5: Lesion area accounts for 25%-50% of the entire leaf area;

Grade 7: Lesion area accounts for more than 50% of the entire leaf area;

Grade 9: The whole leaf is diseased and wilted.

Calculate the disease index and preventive effect according to the following formula

Table 1 Composition of the present invention is to the preventive effect of tomato late blight

Table 1 clearly shows that the actual control effect of a fungicidal composition containing pyridine amide compounds on tomato late blight is higher than the control effect calculated by the Colby formula, that is, there is a synergistic effect.

Trial 2: Apple Scab

Take apple scab diseased leaves, moisten and cultivate for 3-4 days to produce spores. Use a brush to dip in distilled water at about 10°C to wash the pathogen spores on the back of the diseased leaves, and make a spore suspension with a concentration of about 5×10 ⁴ /mL.

The fungicidal activity of pesticides against apple scab was determined by live pot method. Greenhouse potted apple seedlings were used as experimental materials. One plant per pot. Seedlings with two unfurled new leaves at the top were selected (old leaves at the bottom of the plant were cut off).

Stems and leaves were evenly sprayed on the potted seedlings for testing. The front and back sides of the leaves to be inoculated were sprayed with each treatment agent until moist, and inoculated 24 hours later. Each pot was treated with 4 repetitions. And the treatment without medicament (containing organic solvent and emulsifier) was set as blank control.

The spore suspension was sprayed and inoculated on the young leaves at the top of vigorously growing new shoots, and immediately placed on a tray covered with a wet towel, with the back of the leaves facing up, sealed with a plastic film, and then placed in an artificial climate box at 25°C for moisture cultivation. After 15 days, the incidence was investigated.

Grading standards:

Level 0: no disease;

Grade 1: Lesion area accounts for less than 5% of the entire leaf area;

Grade 3: Lesions account for 6%-10% of the entire leaf area;

Grade 5: The lesion area accounts for 11%-20% of the entire leaf area;

Grade 7: Lesions account for 21%-40% of the entire leaf area;

Grade 9: The lesion area accounts for more than 40% of the entire leaf area.

Table 2 Composition of the present invention is to the preventive effect of apple scab

Table 2 clearly shows that the actual control effect of a fungicidal composition containing pyridine amide compounds on apple scab is higher than the control effect calculated by the Colby formula, that is, there is a synergistic effect.

Claims

A bactericidal composition comprising pyridine amide compounds, characterized in that it contains the active ingredient compound I

and fluthiapiprofen, the weight ratio of the compound I to fluthiapiprofen is 50:1-1:25.
The fungicidal composition comprising pyridine amide compounds according to claim 1, characterized in that the weight ratio of compound I to fluthiapiprofen is 25:1-1:25.
The bactericidal composition comprising pyridine amide compounds according to claim 1, wherein the weight ratio of compound I and fluthiapiprofen is 20:1-1:20.
The bactericidal composition comprising pyridine amide compounds according to claim 1, wherein the weight ratio of the compound I and fluthiapiprofen is 20:1-1:10.
The fungicidal composition comprising pyridine amide compounds according to claim 1, wherein the weight ratio of the compound I and fluthiapiprofen is 10:1-1:10.
The fungicidal composition comprising pyridine amide compounds according to claim 1, characterized in that the weight ratio of compound I to fluthiapiprofen is 10:1-1:5.
The bactericidal composition comprising pyridine amide compounds according to claim 1, wherein the weight ratio of compound I to fluthiapiprofen is 10:1-1:2.
The bactericidal composition comprising pyridine amide compounds according to claim 1, characterized in that, the bactericidal composition further comprises a filler and/or a surfactant.
The use of the fungicidal composition comprising pyridine amide compounds according to claim 1 for preventing or controlling fungal diseases on grapevines, cereals, fruits, leguminous plants, oil plants, melon plants, fiber plants, and vegetables.
The fungicidal composition comprising pyridine amide compounds according to claim 1 is used for preventing or controlling cucumber downy mildew, grape downy mildew, tomato late blight, wheat powdery mildew, rice blast, cucumber anthracnose, wheat leaf rust, Apple scab, pear scab, tomato early blight, grape gray mold, rape sclerotinia, soybean rust.
A method for preventing or controlling plants, plant parts, plant propagation materials and subsequently grown plant organs from attack by phytopathogenic bacteria, characterized in that it comprises the bactericidal combination comprising the pyridine amide compounds described in claim 1 The application of an agent to a plant, plant part, plant propagation material, or soil or growing medium in which the plant is growing or needs to grow.
The method according to claim 11, characterized in that, comprising applying the fungicidal composition according to claim 1 to plants, plant parts, before or after the plants are infected by pathogenic bacteria Plant propagation material or the soil or growing medium in which plants are growing or are required to grow.
A method for protecting seeds, seedling roots and branches against phytopathogenic bacteria, comprising making seeds and the bactericidal composition comprising picolinamide compounds described in claim 1 before sowing and/or after germination touch.
A method for preventing and controlling soil harmful bacteria, characterized in that the fungicidal composition comprising pyridine amide compounds according to claim 1 is applied to soil and/or directly to plants before germination, after germination or before and after germination. The soil that the roots touch or the soil that is suitable for plant growth.