A bactericidal composition containing triazole compounds

By preparing a bactericidal composition containing triazole compounds, the problems of improving the efficacy and delaying resistance after the combination of Cyclobutrifluram and triazole bactericidal in the prior art are solved, and the effect of reducing the dosage and enhancing the prevention and treatment effect is achieved.

CN117941693BActive Publication Date: 2025-08-08QINGDAO HAILIER BIOTECHNOLOGY CO LTD
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Patent Information

Application Number
CN202410117281.2
Authority / Receiving Office
CN · China
Patent Type
Patents(China)
Current Assignee / Owner
Filing Date
2024-01-29
Publication Date
2025-08-08
Estimated Expiration
2044-01-29

AI Technical Summary

Technical Problem

In the prior art, although the combination of Cyclobutrifluram and triazole fungicides has improved the prevention and treatment effect, how to further enhance the efficacy, reduce the dosage and delay the development of drug resistance is still a challenge in the field of pesticides.

Method used

A bactericidal composition containing triazole compounds is provided, comprising active ingredients A and B, with a mass ratio of 35:1 to 1:35, supplemented with agriculturally permitted additives, and is prepared into various dosage forms for the prevention and control of plant fungal diseases.

Benefits of technology

It enhances the efficacy of the drug, reduces the use of pesticides, extends the effectiveness period, and delays the development of drug resistance. At the same time, it has a significant increase in yield and guarantees for crops and non-target biosafety.

✦ Generated by Eureka AI based on patent content.

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Abstract

The present invention relates to a fungicide composition containing a triazole compound and its use. The composition comprises an active ingredient A and an active ingredient B, wherein the active ingredient A is cyclobutrifluram and the active ingredient B is a triazole compound selected from flutriafol, hexaconazole, and diniconazole. The fungicide composition or its formulation of the present invention can enhance drug efficacy, reduce drug dosage, improve control effectiveness, and delay the development of drug resistance.
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Description

Technical Field

[0001] The present invention relates to the field of pesticide fungicides, and in particular to a fungicide composition containing triazole compounds. Background Art

[0002] Cyclobutrifluram is a new nicotinamide fungicide and nematicide developed by Syngenta. It boasts a broad spectrum of efficacy, safety, and effectiveness against various nematodes and major fungal diseases. Direct application or seed treatment effectively controls root knots, beet cysts, and corn short-bodies in crops like cucumbers, tomatoes, corn, and sugar beets. It also effectively controls plant diseases, particularly Fusarium. Its CAS registration number is 1460292-16-3. Its chemical structure is as follows:

[0003]

[0004] Triazole fungicides utilize triazole rings to coordinate with the iron atom of the iron porphyrin in bacteria, hindering the formation of the iron-oxygen complex of the iron porphyrin, thereby inhibiting the synthesis of ergosterol and ultimately leading to bacterial death due to cell membrane damage. Triazole fungicides primarily include triadimefon, triadimenol, uniconazole, flutriafol, hexaconazole, diniconazole, paclobutrazol, propiconazole, difenoconazole, fluconazole, clofoconazole, tebuconazole, myclobutrazol, and prothioconazole.

[0005] Flutriafol is a triazole sterol demethylation inhibitor fungicide that can effectively inhibit the biosynthesis of ergosterol and cause the rupture of fungal cell walls. It has a broad-spectrum antibacterial activity and strong systemic properties, and has good protective and therapeutic effects on many fungal diseases caused by basidiomycetes and ascomycetes.

[0006] Hexaconazole is a sterol demethylation inhibitor that disrupts and prevents the biosynthesis of ergosterol, a key component of bacterial cell membranes. This prevents cell membrane formation and leads to bacterial death. It possesses systemic, protective, and therapeutic activities. It effectively prevents diseases caused by Ascomycetes, Basidiomycetes, and Deuteromycetes. It is particularly effective in protecting against and eradicating diseases caused by Basidiomycetes and Ascomycetes, such as powdery mildew, rust, scab, brown spot, and anthracnose.

[0007] Diniconazole inhibits 14a-demethylation in the biosynthesis of ergosterol in fungi, causing ergosterol deficiency, leading to abnormal fungal cell membranes and ultimately fungal death, and has protective, therapeutic and eradication effects.

[0008] This study investigates the application of cyclobutrifluram in fungal diseases. Numerous experimental results demonstrate that a rational combination of cyclobutrifluram with the triazole fungicides fluconazole, hexaconazole, and diniconazole effectively enhances control efficacy. With increasing environmental and food safety requirements and the growing concern for pesticide resistance, the scientific use of pesticides, reduced dosage, and improved efficacy have become pressing challenges in the pesticide field. Summary of the Invention

[0009] Based on the above situation, the purpose of the present invention is to provide a fungicidal composition containing triazole compounds and its preparation, which are mainly used to prevent and control plant fungal diseases. The composition or its preparation can enhance the efficacy, reduce the dosage, and at the same time prolong the lasting effect and delay the development of drug resistance.

[0010] In order to achieve the above object, the following technical solution is provided: a fungicide composition containing a triazole compound, comprising active ingredient A and active ingredient B, wherein the active ingredient A is a compound represented by formula (I)

[0011] The active ingredient B is a triazole compound, and the triazole compound is selected from any one of flutriafol, hexaconazole, and diniconazole;

[0012] Furthermore, the mass ratio of active ingredient A to active ingredient B is 35:1 to 1:35;

[0013] Furthermore, the mass ratio of the compound of formula (I) to flutriafol is 1:35 to 30:1;

[0014] Furthermore, the mass ratio of the compound of formula (I) to flutriafol is 1:35, 1:20, 1:12, 2:9, 1:1, 2:1, 5:1, 10:1, 24:1, and 30:1;

[0015] Furthermore, the mass ratio of the compound of formula (I) to flutriafol is 1:20 to 30:1;

[0016] Furthermore, the mass ratio of the compound of formula (I) to flutriafol is 1:20, 1:12, 2:9, 1:1, 2:1, 5:1, 10:1, 24:1, 30:1

[0017] Furthermore, the mass ratio of the compound of formula (I) to hexaconazole is 1:30 to 24:1;

[0018] Furthermore, the mass ratio of the compound of formula (I) to hexaconazole is 1:30, 1:16, 1:8, 2:5, 1:1, 2:1, 3:1, 9:1, 25:2, 24:1;

[0019] Furthermore, the mass ratio of the compound of formula (I) to hexaconazole is 1:16 to 24:1;

[0020] Furthermore, the mass ratio of the compound of formula (I) to hexaconazole is 1:16, 1:8, 2:5, 1:1, 2:1, 3:1, 9:1, 25:2, 24:1;

[0021] Furthermore, the mass ratio of the compound of formula (I) to diniconazole is 1:20 to 35:1;

[0022] Furthermore, the mass ratio of the compound of formula (I) to diniconazole is 1:20, 2:25, 1:10, 1:2, 5:4, 5:2, 5:1, 12:1, 25:2, and 35:1;

[0023] Furthermore, the mass ratio of the compound of formula (I) to diniconazole is 1:20 to 25:2;

[0024] Furthermore, the mass ratio of the compound of formula (I) to diniconazole is 1:20, 2:25, 1:10, 1:2, 5:4, 5:2, 5:1, 12:1, and 25:2;

[0025] Furthermore, based on the total weight of the bactericidal composition being 100 wt%, the sum of the content of the active ingredient A and the active ingredient B in the bactericidal composition is 1 to 90 wt%;

[0026] Furthermore, based on the total weight of the bactericidal composition being 100 wt%, the sum of the contents of the active ingredient A and the active ingredient B in the bactericidal composition is preferably 5 to 80 wt%;

[0027] Furthermore, the fungicidal composition contains, in addition to the active ingredient, agriculturally acceptable auxiliary ingredients, wherein the auxiliary ingredients are selected from one or more of a wetting agent, a dispersant, an emulsifier, a thickener, a disintegrant, an antifreeze agent, a defoaming agent, a solvent, a preservative, a stabilizer, a synergist, a binder or a carrier;

[0028] Further, the wetting agent is selected from one or more of alkylbenzene sulfonate, alkylnaphthalene sulfonate, lignin sulfonate, sodium lauryl sulfate, sodium dioctyl sulfosuccinate, α-olefin sulfonate, alkylphenol polyoxyethylene ether, castor oil polyoxyethylene ether, alkylphenol ethoxylate, fatty alcohol ethoxylate, fatty alcohol polyoxyethylene ether sodium sulfate, silkworm feces, soapberry powder, soapberry powder, SOPA, detergent, emulsifier 2000 series and wetting penetrant F; and / or

[0029] Furthermore, the dispersant is selected from one or more of lignin sulfonate, alkylnaphthalene sulfonate formaldehyde condensate, naphthalene sulfonate, tristyrylphenol ethoxylate phosphate, fatty alcohol ethoxylate, alkylphenol polyoxyethylene ether, alkylphenol polyoxyethylene ether methyl ether condensate sulfate, fatty amine polyoxyethylene ether, glycerol fatty acid ester polyoxyethylene ether, polycarboxylates, polyacrylic acids, phosphates, EO-PO block copolymers and EO-PO graft copolymers; and / or

[0030] Furthermore, the emulsifier is selected from one or more of calcium dodecylbenzenesulfonate, alkylphenol formaldehyde resin polyoxyethylene ether, phenylethylphenol polyoxyethylene polyoxypropylene ether, fatty alcohol ethylene oxide-propylene oxide copolymer, styrylphenol polyoxyethylene ether, castor oil polyoxyethylene ether and alkylphenol ether phosphate; and / or

[0031] Furthermore, the thickener is selected from one or more of xanthan gum, organobentonite, gum arabic, sodium alginate, magnesium aluminum silicate, carboxymethyl cellulose and white carbon black; and / or

[0032] Furthermore, the disintegrant is selected from one or more of sodium sulfate, ammonium sulfate, aluminum chloride, sodium chloride, ammonium chloride, bentonite, glucose, sucrose, starch, cellulose, urea, sodium carbonate, sodium bicarbonate, citric acid and tartaric acid; and / or

[0033] Furthermore, the antifreeze agent is selected from one or more of alcohols, alcohol ethers, chlorinated hydrocarbons and inorganic salts; and / or

[0034] Further, the defoaming agent is selected from C 10 -C 20 Saturated fatty acid compounds, silicone oil, silicone compounds, C8-C 10 One or more of fatty alcohols; and / or

[0035] Furthermore, the solvent is selected from one or more of benzene, toluene, xylene, durene, methanol, ethanol, isopropanol, n-butanol, dimethyl sulfoxide, dimethylformamide, cyclohexanone, alkylene carbonate, diesel, solvent oil, vegetable oil (soybean oil, corn oil, rapeseed oil, palm oil, etc.), vegetable oil derivatives and water; and / or

[0036] Furthermore, the preservative is selected from one or more of propionic acid, sodium propionate, sorbic acid, sodium sorbate, potassium sorbate, benzoic acid, sodium benzoate, sodium p-hydroxybenzoate, methyl p-hydroxybenzoate, kasone and 1,2-benzisothiazolin-3-one; and / or

[0037] Furthermore, the stabilizer is selected from one or more of disodium hydrogen phosphate, oxalic acid, succinic acid, adipic acid, borax, 2,6-di-tert-butyl-p-methylphenol, triethanolamine oleate, epoxidized vegetable oil, kaolin, diatomaceous earth, bentonite, attapulgite, white carbon black, talc, montmorillonite and starch; and / or

[0038] Furthermore, the synergist is selected from phosphine, piperonyl butoxide; and / or

[0039] Furthermore, the carrier is selected from one or more of ammonium salts, ground natural minerals, ground artificial minerals, silicates, resins, waxes, solid fertilizers, water, organic solvents, mineral oils, vegetable oils and vegetable oil derivatives.

[0040] Furthermore, the formulation of the fungicide composition is selected from solid preparations and / or liquid preparations and / or seed treatment preparations;

[0041] The solid preparations include powders, granules, pellets, tablets, strips, wettable powders, oil-dispersible powders, emulsion powders, water-dispersible granules, emulsion granules, water-dispersible tablets, soluble powders, soluble tablets or soluble granules;

[0042] The liquid preparations include soluble solutions, soluble gels, oils, film-spreading oils, emulsifiable concentrates, latexes, dispersible solutions, ointments, aqueous emulsions, oil emulsions, microemulsions, fats, suspensions, microcapsule suspensions, oil suspensions, dispersible oil suspensions, suspoemulsions, microcapsule suspension-suspension concentrates, microcapsule suspension-water emulsions, or microcapsule suspension-suspoemulsions;

[0043] Furthermore, the powder is a free-flowing powder preparation containing the active ingredient suitable for dusting or spreading;

[0044] Furthermore, the granules are free-flowing granular preparations containing active ingredients within a certain particle size range;

[0045] Furthermore, the spherical preparation is a spherical preparation (generally with a diameter greater than 6 mm) containing an active ingredient;

[0046] Furthermore, the tablet is a sheet-like preparation containing an active ingredient with a certain shape and size (usually having two flat or convex surfaces, with the distance between the two surfaces being less than the diameter);

[0047] Furthermore, the strips are strip- or rod-shaped preparations containing active ingredients (generally a few centimeters in length and a few millimeters in width / diameter, i.e., the length is greater than the diameter / width);

[0048] Furthermore, the wettable powder is a powdered preparation in which the active ingredient is dispersed into a suspension in water;

[0049] Furthermore, the oil-dispersible powder is a powdered preparation in which the active ingredient is dispersed into a suspension in an organic solvent;

[0050] Furthermore, the emulsion powder is a powdered preparation in which the active ingredient is dissolved in an organic solvent, encapsulated in a soluble or insoluble inert ingredient, and dispersed in water to form an oil-in-water emulsion;

[0051] Furthermore, the water dispersible granules are granular preparations that disintegrate in water and disperse the active ingredients into a suspension;

[0052] Furthermore, the emulsifiable granules are granular preparations in which the active ingredients are dissolved in an organic solvent, encapsulated in a soluble or insoluble inert ingredient, and dispersed in water to form an oil-in-water emulsion;

[0053] Furthermore, the water-dispersible tablet is a sheet-like preparation that disintegrates in water and disperses the active ingredients into a suspension;

[0054] Furthermore, the soluble powder is a powdered preparation in which the active ingredient forms a true solution in water and may contain inert ingredients that are insoluble in water;

[0055] Furthermore, the soluble granules are granular preparations in which the active ingredient forms a true solution in water and may contain inert ingredients that are insoluble in water;

[0056] Furthermore, the soluble tablet is a sheet-like preparation in which the active ingredient forms a true solution in water and may contain an inert ingredient that is insoluble in water;

[0057] Furthermore, the soluble preparation is a transparent or translucent liquid preparation containing an active ingredient that is diluted with water and may contain an inert component that is insoluble in water;

[0058] Furthermore, the soluble gel is a colloidal preparation containing active ingredients that is diluted with water to form a true solution;

[0059] Furthermore, the oil preparation is a liquid preparation diluted with an organic solvent (or not diluted) to form a homogeneous phase and containing an active ingredient;

[0060] Furthermore, the film-spreading oil is an oil containing active ingredients that automatically spreads on the water surface to form an oil film;

[0061] Furthermore, the emulsifiable concentrate is a homogeneous liquid preparation containing active ingredients that is dispersed into an emulsion by dilution with water;

[0062] Furthermore, the latex is a latex preparation containing active ingredients that is diluted and dispersed into an emulsion with water;

[0063] Furthermore, the dispersible liquid preparation is diluted with water and dispersed into a homogeneous liquid preparation containing the active ingredient in suspension;

[0064] Furthermore, the ointment is a water-based paste preparation containing active ingredients that can form a film and is generally used directly;

[0065] Furthermore, the aqueous emulsion is an emulsion liquid preparation in which the active ingredient (or its organic solution) is dissolved in water;

[0066] Furthermore, the oil emulsion is an emulsion liquid preparation in which the active ingredient (or its aqueous solution) is contained in oil;

[0067] Furthermore, the microemulsion is a transparent or translucent microemulsion liquid preparation in which the active ingredient is dissolved in water and is used directly or after being diluted with water;

[0068] Furthermore, the fat agent is an oil or fat-based viscous preparation containing active ingredients, which is generally used directly;

[0069] Furthermore, the suspension concentrate is a stable suspension liquid preparation in which the active ingredient is dispersed in water as solid particles, and is generally diluted with water for use;

[0070] Furthermore, the microcapsule suspension is a stable suspension liquid preparation formed by microcapsules containing active ingredients dispersed in a liquid;

[0071] Furthermore, the oil suspension concentrate is a stable suspension liquid preparation in which the active ingredient is dispersed in a liquid as solid particles, and is generally diluted with an organic solvent for use;

[0072] Furthermore, the dispersible oil suspension concentrate is a stable suspension liquid preparation in which the active ingredient is dispersed in a non-aqueous medium as solid particles, and is generally diluted with water for use;

[0073] Furthermore, the suspoemulsion is a heterogeneous liquid preparation in which the active ingredient is stably dispersed in the form of solid particles and water-insoluble tiny droplets in a continuous aqueous phase;

[0074] Furthermore, the microcapsule suspension-suspension concentrate is a stable suspension liquid preparation in which the active ingredient is dispersed in water in the form of microcapsules and solid particles;

[0075] Furthermore, the microcapsule suspension-water emulsion is a heterogeneous liquid preparation in which the active ingredients are stably dispersed in the form of microcapsules and tiny droplets in a continuous aqueous phase;

[0076] Furthermore, the microcapsule suspension-suspoemulsion is a heterogeneous liquid preparation in which the active ingredients are stably dispersed in the form of microcapsules, solid particles and tiny droplets in a continuous aqueous phase;

[0077] Furthermore, the fungicide composition can be prepared into a formulation acceptable for pesticides, and the formulation is a microemulsion, an aqueous emulsion, a suspension, a dispersible oil suspension, a soluble concentrate, an emulsifiable concentrate, a suspoemulsion, a microcapsule suspension, a water-dispersible granule, a wettable powder, a granule, a seed treatment suspension, or a seed treatment dry powder.

[0078] Furthermore, the formulation is in the form of a microemulsion, emulsifiable concentrate, suspension concentrate, aqueous emulsion, water-dispersible granules, or seed treatment suspension concentrate.

[0079] The present invention also discloses the use of the above-mentioned fungicide composition in preventing and controlling plant diseases;

[0080] Furthermore, the plant disease is a plant disease caused by fungi or bacteria;

[0081] Furthermore, the plant disease is a plant disease caused by fungi;

[0082] Furthermore, the plant disease caused by the fungus is wheat fusarium wilt.

[0083] Beneficial effects of the present invention:

[0084] (1) Increased bactericidal activity, expanded the scope of application, and significantly increased production;

[0085] (2) It has broad development prospects, reduces the use of pesticides, and lowers agricultural costs;

[0086] (3) It is safe and efficient, safe for crops, non-target organisms, beneficial organisms and natural enemies, and has the effect of increasing production and ensuring income. DETAILED DESCRIPTION

[0087] In order to make the technical solutions, objectives and advantages of the present invention more clearly understood, the present invention is described with reference to the following specific embodiments. However, the present invention can be implemented in various forms and should not be limited to the embodiments described herein.

[0088] Indoor bioassay of wheat scab

[0089] Test basis: Refer to the Agricultural Industry Standard of the People's Republic of China, Guidelines for Indoor Bioassay Test of Pesticides, Fungicides Part 2: Test for Inhibition of Pathogenic Fungal Mycelial Growth, Plate Method NT / T 1156.2-2006.

[0090] The test pathogen, Fusarium graminearum, was isolated from diseased wheat ears collected from Henan Province. A pink mold layer was found at the base of the glume on the wheat ears. The pink mold layer was picked off with a toothpick and placed on a culture medium. The culture was then incubated in a constant temperature incubator and set aside.

[0091] Test agents: 95% fluconazole technical, 95% hexaconazole technical, 96% diniconazole technical, all of which are provided by the group's R&D center.

[0092] Preparation: Dissolve the test stock drug in acetone and then dilute with a 0.1% Tween 80 aqueous solution. Prepare a single-dose stock solution and set five concentration series based on the mixing purpose and drug activity. The final organic solvent content should not exceed 2%.

[0093] Melt the PDA culture medium in a microwave oven and cool it to about 50°C. Then, according to the principle of increasing the concentration from low to high, take 1 mL of the prepared drug solution and 9 mL of PDA culture medium and add them to a 9 cm diameter culture dish. Mix well to prepare drug-containing plates of corresponding concentrations.

[0094] Inoculation: Use a 5mm diameter puncher to punch the activated pathogenic fungi into a cake under sterile conditions. After the drug-containing culture medium solidifies, place the cake in the center of the culture medium. Finally, seal the culture dish with sealing film and place it in an incubator at 27°C for culture. At the same time, set up a blank solution without drug as a blank control. Repeat each treatment three times.

[0095] Investigation: Investigate the growth of pathogenic mycelia based on the growth of mycelia in the blank control culture dish. After 72 hours of incubation, measure the diameter of the colonies with a caliper in centimeters (cm). Measure the diameter of each colony once vertically using the cross-hatch method and take the average value.

[0096] The mycelial growth inhibition rate was calculated according to the following formula, and the unit was percentage (%), and the calculation result was rounded to two decimal places.

[0097] D=D1-D2·············(1)

[0098] D——colony growth diameter;

[0099] D1 - colony diameter;

[0100] D2——diameter of mushroom cake.

[0101] I=(D0-D t ) / D0*100·············(2)

[0102] Where:

[0103] I——hyphae growth inhibition rate;

[0104] D0——blank control colony growth diameter;

[0105] D t ——The growth diameter of the colony after treatment with chemicals.

[0106] Statistical analysis: Regression analysis was performed based on the logarithmic values of each agent concentration and the corresponding probability value of mycelial growth inhibition rate to calculate the EC of each agent. 50 The correlation coefficient R is used to evaluate the activity of the test agent on the biological test material.

[0107] Sun Yunpei method: The synergistic effect of mixed drugs is evaluated based on the co-toxicity coefficient (CTC). A co-toxicity coefficient of CTC ≥ 120 indicates a synergistic effect; CTC ≤ 80 indicates an antagonistic effect; and 80 < CTC < 120 indicates an additive effect.

[0108] The co-toxicity coefficient (CTC value) of the mixture is calculated according to formula (3), formula (4), and formula (5):

[0109]

[0110] Where:

[0111] ATI - measured toxicity index of mixture;

[0112] S——EC of standard fungicide 50 , the unit is milligrams per liter (mg / L);

[0113] M——EC of the mixture 50 , the unit is milligrams per liter (mg / L).

[0114] TTI=TI A * P A +TI B * P B ·······(4)

[0115] Where:

[0116] TTI – Theoretical Toxicity Index of Mixtures;

[0117] TI A ——Agent toxicity index;

[0118] P A ——The percentage of agent A in the mixture, in percentage (%);

[0119] TI B ——Toxicity index of agent B;

[0120] P B ——The percentage of agent B in the mixture, in percentage (%).

[0121]

[0122] Where:

[0123] CTC – Co-toxicity coefficient;

[0124] ATI - measured toxicity index of mixture;

[0125] TTI - Theoretical Toxicity Index of Mixture.

[0126] Example 1

[0127] Indoor bioassay of cyclobutrifluram and flutriafol against wheat scab

[0128] The results in Table 1 show that Cyclobutrifluram can control wheat scab EC 50 The EC value of flutriafol for controlling wheat scab is 4.424 mg / L. 50 The ratio of Cyclobutrifluram to flutriafol in the ratio of 1:35 to 30:1 was 4.139 mg / L. The ratio of Cyclobutrifluram to flutriafol in the ratio of 1:35 to 30:1 showed good control effect. The ratio of Cyclobutrifluram to flutriafol in the ratio of 1:20 to 30:1 was greater than 120, showing synergistic effect. Among them, the ratio of Cyclobutrifluram to flutriafol in the ratio of 1:1 was the largest, which was 203.752, greater than 120. 50 It is 2.099 mg / L, showing a synergistic effect.

[0129] Table 1 Results of synergistic effects of different ratios of cyclobutrifluram and flutriafol on wheat scab

[0130] Test drug Regression equation <![CDATA[r 2 ]]> <![CDATA[EC 50 ]]> Co-toxicity coefficient effect Biopesticide B value ± standard error / (mg / L) (ATI) (TTI) (CTC) / Cyclobutrifluram(A) 1.346±0.186 0.972 4.424(3.387~5.778) 100.000 / / / Flutriafol (B) 1.424±0.180 0.976 4.139(3.244~5.280) 106.886 / / / A:B=1:35 1.487±0.226 0.966 4.768(3.541~6.420) 92.785 106.694 86.964 Additive effect A:B=1:20 1.907±0.159 0.989 2.951(2.512~3.466) 149.915 106.558 140.689 Synergistic effect A:B=1:12 1.996±0.215 0.983 2.669(2.151~3.313) 165.755 106.356 155.849 Synergistic effect A:B=2:9 1.954±0.166 0.989 2.329(1.974~2.747) 189.953 105.634 179.822 Synergistic effect A:B=1:1 2.025±0.068 0.998 2.099(1.966~2.241) 210.767 103.443 203.752 Synergistic effect A:B=2:1 2.049±0.192 0.987 2.424(2.017~2.913) 182.508 102.295 178.413 Synergistic effect A:B=5:1 2.092±0.263 0.977 2.596(2.021~3.335) 170.416 101.148 168.482 Synergistic effect A:B=10:1 1.958±0.208 0.983 2.997(2.444~3.676) 147.614 100.626 146.696 Synergistic effect A:B=24:1 1.633±0.167 0.984 3.145(2.582~3.829) 140.668 100.275 140.281 Synergistic effect A:B=30:1 1.805±0.191 0.983 3.503(2.849~4.307) 126.292 100.222 126.012 Synergistic effect

[0131] Note: The above data were analyzed using DPS statistical analysis software, and the values were rounded to 3 decimal places. The same applies to Tables 2 and 3 below.

[0132] Example 2

[0133] Indoor bioassay of cyclobutrifluram and hexaconazole against wheat scab

[0134] The results in Table 2 show that the EC value of hexaconazole for controlling wheat scab 50 The ratio of Cyclobutrifluram to hexaconazole in the ratio of 1:30 to 24:1 showed good control effect. The ratio of Cyclobutrifluram to hexaconazole in the ratio of 1:16 to 24:1 showed a co-toxicity coefficient greater than 120, showing a synergistic effect. Among them, the co-toxicity coefficient of Cyclobutrifluram to hexaconazole in the ratio of 2:1 was the largest, at 220.817, which was greater than 120. 50 It is 1.491 mg / L, showing a synergistic effect.

[0135] Table 2 Results of synergistic effects of different ratios of cyclobutrifluram and hexaconazole on wheat scab

[0136]

[0137]

[0138] Example 3

[0139] Indoor bioassay of cyclobutrifluram and diniconazole against wheat scab

[0140] The results in Table 3 show that the EC of diniconazole for controlling wheat scab 50 The ratio of Cyclobutrifluram to diniconazole in the ratio of 1:20 to 35:1 showed good control effect. The co-toxicity coefficient of Cyclobutrifluram to diniconazole in the ratio of 1:20 to 25:2 was greater than 120, showing a synergistic effect. Among them, the co-toxicity coefficient of Cyclobutrifluram to diniconazole in the ratio of 5:2 was the largest, at 217.892, which was greater than 120. 50 It is 1.450mg / L, with significant efficiency improvement.

[0141] Table 3 Results of synergistic effects of different ratios of cyclobutrifluram and diniconazole on wheat scab

[0142] Test drug Regression equation <![CDATA[r 2 ]]> <![CDATA[EC 50 ]]> Co-toxicity coefficient effect Biopesticide B value ± standard error / (mg / L) (ATI) (TTI) (CTC) / Cyclobutrifluram(A) 1.400±0.1575 0.981 4.502(3.6216~5.597) 100.000 / / / Diniconazole (B) 1.269±0.1256 0.985 1.810(1.495~2.191) 248.729 / / / A:B=1:20 1.501±0.1061 0.992 1.498(1.300~1.726) 300.534 241.647 124.369 Synergistic effect A:B=2:25 1.505±0.1147 0.991 1.447(1.240~1.688) 311.126 237.712 130.884 Synergistic effect A:B=1:10 1.667±0.0742 0.997 1.249(1.136~1.374) 360.448 235.208 153.246 Synergistic effect A:B=1:2 1.624±0.0662 0.997 1.278(1.173~1.393) 352.269 199.153 176.884 Synergistic effect A:B=5:4 1.525±0.085 0.995 1.373(1.224~1.540) 327.895 166.102 197.406 Synergistic effect A:B=5:2 1.562±0.1039 0.993 1.450(1.268~1.659) 310.483 142.494 217.892 Synergistic effect A:B=5:1 1.436±0.1734 0.978 2.177(1.725~2.747) 206.798 124.788 165.719 Synergistic effect A:B=12:1 1.500±0.0831 0.995 2.503(2.2464~2.788) 179.864 111.441 161.399 Synergistic effect A:B=25:2 1.552±0.1241 0.990 2.767(2.3718~3.220) 162.703 111.017 146.557 Synergistic effect A:B=35:1 1.579±0.1142 0.992 3.71 0(3.227~4.264) 121.348 104.131 116.533 Additive effect

[0143] Formulation Examples

[0144] Preparation Example 1:

[0145] 40% Cyclobutrifluram·Flutriafol WP (20:20)

[0146] The active ingredient A, Cyclobutrifluram, is 20%, the active ingredient B, Flutriafol, is 20%, the wetting agent is alkylnaphthalene sulfonate, 5.5%, the dispersant is sodium naphthaldehyde condensate sulfonate, 6%, kaolin is 10%, and expanded clay is added to 100%. The active ingredients and additives are mixed uniformly, initially pulverized in a mechanical pulverizer, then pulverized in a jet mill, and then mixed uniformly to produce a 40% cyclobutrifluram and flutriafol wettable powder.

[0147] Preparation Example 2:

[0148] 42% Cyclobutrifluram·diniconazole wettable powder (30:12)

[0149] Active ingredient A (Cyclobutrifluram) 30%, active ingredient B (Diniconazole) 12%, wetting agent (Alkylnaphthalenesulfonate) 8%, dispersant (Sodium naphthalene formaldehyde condensate sulfonate) 4%, kaolin 15%, and expanded clay to 100%. The active ingredients and additives are mixed uniformly, initially pulverized in a mechanical mill, then pulverized in a jet mill, and then mixed uniformly to produce a 42% wettable powder of Cyclobutrifluram and Diniconazole.

[0150] Preparation Example 3:

[0151] 30% Cyclobutrifluram·flutriafol suspension (16:14)

[0152] Active ingredient A: Cyclobutrifluram 16%, active ingredient B: trifloxylate 14%, wetting agent: lignin sulfonate 6%, dispersant: sodium alkylnaphthalene formaldehyde condensate sulfonate 2.5%, antifreeze: ethylene glycol 5%, thickener: xanthan gum 0.1%, magnesium aluminum silicate 0.25%, and deionized water to 100%. Add the active ingredient, wetting agent, dispersant, antifreeze, and water to a stirred tank, stir thoroughly, and grind to D using a sand mill. 90 (90% of the particles have a particle size of <10 μm). After grinding, the mixture is pumped into a high-speed shearing machine, a thickener is added, and high-speed shearing is performed. After shearing, a 30% cyclobutrifluram·flutriafol suspension concentrate is obtained.

[0153] Preparation Example 4:

[0154] 21% Cyclobutrifluram·Hexaconazole Suspension (14:7)

[0155] Active ingredient A: Cyclobutrifluram 14%, active ingredient B: Hexaconazole 7%, wetting agent: lignin sulfonate 4.5%, dispersant: sodium alkylnaphthalene formaldehyde condensate sulfonate 3%, antifreeze: ethylene glycol 5%, thickener: organic bentonite 0.1%, magnesium aluminum silicate 0.2%, and deionized water to 100%. The active ingredient, wetting agent, dispersant, antifreeze, and water were added to a stirred tank, stirred thoroughly, and then ground using a sand mill to D 90 (90% of the particles have a particle size of <10 μm). After grinding, the mixture is pumped into a high-speed shearing machine, a thickener is added, and high-speed shearing is performed. After shearing, a 21% cyclobutrifluram·hexaconazole suspension is obtained.

[0156] Preparation Example 5:

[0157] 24% Cyclobutrifluram·diniconazole suspension (15:9)

[0158] Active ingredient A: Cyclobutrifluram 15%, active ingredient B: diniconazole 9%, wetting agent: lignin sulfonate 4.5%, dispersant: sodium alkylnaphthalene formaldehyde condensate sulfonate 3.5%, antifreeze: ethylene glycol 1%, glycerol 2.5%, thickener: magnesium aluminum silicate 0.2%, and deionized water to 100%. Add the active ingredient, wetting agent, dispersant, antifreeze, and water to a stirred tank, stir thoroughly, and grind to D using a sand mill. 90 (90% of the particles have a particle size of <10 μm). After grinding, the mixture is pumped into a high-speed shearing machine, a thickener is added, and high-speed shearing is performed. After shearing, a 24% cyclobutrifluram·diniconazole suspension is obtained.

[0159] Preparation Example 6:

[0160] 35% Cyclobutrifluram·Flutriafol dispersible oil suspension (15:20)

[0161] Active ingredient A: Cyclobutrifluram 15%, active ingredient B: flutriafol 20%, emulsifier: calcium dodecylbenzenesulfonate 2.5%, alkylphenol formaldehyde resin polyoxyethylene ether 3%, dispersant: alkylphenol polyoxyethylene ether 4.5%, thickener: xanthan gum 2%, and corn oil to 100%. The active ingredients, surfactant, and other functional additives are placed in a reactor in sequence, oil is added and mixed thoroughly. The mixture is then subjected to high-speed shearing, wet sand milling, and finally homogenized filtration to obtain a 35% cyclobutrifluram flutriafol dispersible oil suspension concentrate.

[0162] Field efficacy trials

[0163] Field trials on the efficacy of pesticides against wheat scab

[0164] Test location: Wheat planting occurs all year round in Hebei Province

[0165] Test time: May 12, 2020, wheat heading period

[0166] Test agents and dosage: See Table 4 for details of the dosage.

[0167] Table 4 Comparison table of pesticide dosage in field test

[0168]

[0169] Experimental treatment: Single-dose and water-controlled, 10-day interval between two applications, spraying time is the wheat ear and flowering stage. Each treatment area of the plot test is 667m 2 , without duplication. Use conventional electric sprayer to spray.

[0170] Survey method: 5-point sampling fixed-point survey. Each treatment point survey 1m 2 10 days before harvest, the total number of ears and the number of diseased ears were investigated. The severity of the disease was divided into 5 levels based on the disease status of the wheat ears:

[0171] Level 0, no disease;

[0172] Level 1: the number of diseased wheat ears accounts for less than 1 / 4 of all wheat ears;

[0173] Level 2: the number of diseased wheat ears accounts for 1 / 4 to 1 / 2 of all wheat ears;

[0174] Level 3: the number of diseased wheat ears accounts for 1 / 2 to 3 / 4 of all wheat ears;

[0175] Level 4: The number of diseased wheat ears accounts for more than 3 / 4 of all wheat ears.

[0176] Calculate the disease index according to disease index = ∑ (number of diseased plants at each level × disease level value) / (total number of plants surveyed × maximum level value);

[0177] The control effect is calculated according to the control effect = (control disease index - treatment disease index) / control disease index;

[0178] Calculate according to unit area 1m 2 Average number of ears and diseased ear rate.

[0179] Samples were taken during the wheat harvest and dried for 3 days to measure the 667m 2 Measured output.

[0180] The data were processed using Microsoft Excel 2003, and the DPS data were statistically analyzed and the difference significance test (Duncan method) was used.

[0181] Example 4

[0182] Results of field trials on efficacy of pesticides against wheat scab

[0183] The results in Table 5 show that, through the field efficacy plot test, the survey results 10 days before harvest showed that the control effects of 40% Cyclobutrifluram·flutriafol wettable powder (20:20), 21% Cyclobutrifluram·hexaconazole suspension concentrate (14:7), and 24% Cyclobutrifluram·diniconazole suspension concentrate (15:9) on wheat scab were 81.89%, 83.18%, and 82.97%, respectively; at the 0.01 and 0.05 levels, there was no significant difference in the control of wheat scab among the three mixed agents; compared with the control single agent 24% Cyclobutrifluram suspension concentrate, 250 g / L flutriafol suspension concentrate, 30% hexaconazole suspension concentrate, and 12.5% diniconazole wettable powder, the mixed preparations were significantly higher than the control single agent.

[0184] Table 5 Control of wheat scab by different compound and single agent

[0185]

[0186] Note: The above processing data are calculated based on the unit area of 1m 2 Average number of ears, diseased ear rate; the control effect % in the above table is the average value of each replicate; lowercase letters represent significant differences at the 5% level, and uppercase letters represent significant differences at the 1% level.

[0187] Table 6 Effects of different pesticides on wheat scab control on wheat yield

[0188]

[0189] Note: The yields in the above table are the average values of each replicate; lowercase letters represent significant differences at the 5% level.

[0190] The results of field efficacy trials showed that the combination of Cyclobutrifluram with fluconazole, hexaconazole and diniconazole not only reduced the diseased ear rate and disease index in the prevention and control of wheat ergot, but also had a significant prevention and control effect, without much impact on yield. The mixed preparation also showed a significant yield-increasing effect.

[0191] In addition, according to observations after the application of the medicine, the wheat in each treatment area grew normally without any pesticide damage, indicating that the wheat growth was safe under the dosage of each agent in this test.

[0192] In laboratory toxicity assays and field trials, the present invention's combination of Cyclobutrifluram and any one of flutriafol, hexaconazole, and diniconazole demonstrated excellent control efficacy against wheat fusarium head blight. The resulting fungicidal composition or formulation exhibits significant control efficacy, exhibiting high efficacy, broad spectrum, low residue, long-lasting efficacy, and strong systemic properties. Furthermore, no phytotoxicity was observed with the combined agent in the trials, demonstrating that the enhanced synergistic fungicidal effect of the resulting fungicidal composition or formulation can reduce production and usage costs and is safe for crops.

[0193] Although the present invention has been described in detail above using general descriptions and specific implementation plans, it is obvious to those skilled in the art that some modifications or improvements can be made thereto based on the present invention. Therefore, these modifications or improvements made without departing from the spirit of the present invention shall fall within the scope of protection claimed by the present invention.

Claims

1. A bactericidal composition containing a triazole compound, characterized in that: The bactericidal composition is composed of active ingredient A and active ingredient B, wherein the active ingredient A is a compound represented by formula (I), and the active ingredient B is flutriafol. (I), the mass ratio of the compound of formula (I) to flutriafol is 1:20~30:

1.

2. The bactericidal composition according to claim 1, characterized in that Based on the total weight of the bactericidal composition being 100 wt %, the sum of the contents of the active ingredient A and the active ingredient B in the bactericidal composition is 1 to 90 wt %.

3. The bactericidal composition according to claim 2, characterized in that Based on the total weight of the bactericidal composition being 100 wt %, the sum of the contents of the active ingredient A and the active ingredient B in the bactericidal composition is 5 to 80 wt %.

4. The bactericidal composition according to claim 1, characterized in that In addition to the active ingredients, the fungicidal composition also contains agriculturally permitted auxiliary ingredients, and the auxiliary ingredients are selected from one or more of wetting agents, dispersants, emulsifiers, thickeners, disintegrants, antifreeze agents, defoaming agents, solvents, preservatives, stabilizers, synergists, binders or carriers.

5. The bactericidal composition according to claim 4, characterized in that The formulation of the fungicide composition is selected from solid formulations and / or liquid formulations and / or seed treatment formulations.

6. The bactericidal composition according to claim 5, characterized in that The fungicide composition can be prepared into a formulation acceptable for pesticides, and the formulation is a microemulsion, an aqueous emulsion, a suspension, a dispersible oil suspension, a soluble solution, an emulsifiable concentrate, a suspoemulsion, a microcapsule suspension, a water-dispersible granule, a wettable powder, a granule, a seed treatment suspension, or a seed treatment dry powder.

7. The bactericidal composition according to claim 6, characterized in that The preparation dosage forms include microemulsion, emulsifiable concentrate, suspension, aqueous emulsion, water-dispersible granules and seed treatment suspension.

8. Use of the fungicidal composition according to any one of claims 1 to 7 in preventing and controlling plant diseases, characterized in that: The plant disease is wheat scab caused by fungi.

Citation Information

Patent Citations

  • Pesticide composition and application thereof

    CN114176087A

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  • Bactericidal composition and application thereof

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