A bactericidal composition and its use

Abstract

The present application relates to a kind of fungicide composition;Also related to the application of the fungicide composition in the field of agriculture, forestry or horticulture in preventing or preventing plant pathogenic fungi from infecting plants.The fungicide composition comprises active ingredient A and active ingredient B, the active ingredient A is formula (I) compound, the active ingredient B is bronopol, kasugamycin, the mass ratio of the active ingredient A and active ingredient B is 1:24-60:1.The fungicide composition of the present application has good control effect on bacterial diseases, especially on cucumber bacterial angular spot disease, and shows significant synergistic effect, which can effectively reduce the amount of drug, reduce agricultural input cost, and delay the resistance of plant pathogenic fungi.

Description

Technical Field

[0001] This invention belongs to the field of pesticide compound technology, specifically relating to a bactericidal composition and its application. Background Technology

[0002] Cucurbitaceae vegetables are among the most widely cultivated major edible vegetables in my country. Bacterial plant diseases seriously threaten food security, characterized by their sudden onset, rapid spread, and difficulty in control. Cucumber bacterial angular leaf spot is a bacterial disease caused by *Pseudomonas syringae* pv. *lachrymans*. It can occur in cucumber seedlings and mature plants, primarily infecting the leaves. Typical symptoms begin as water-soaked, nearly circular, sunken spots, later turning slightly yellowish-brown, causing the leaves to dry out. It spreads rapidly, and in severe cases, can reduce cucumber yield by 50% or even result in total crop failure.

[0003] Currently, chemical control remains the primary method for controlling bacterial plant diseases. However, the available pesticides are numerous, inconsistent, and of limited efficacy. Faced with increasing control pressure, some producers resort to inappropriate methods such as applying excessive amounts, leading to problems like excessive residues. This invention combines the compound of formula (I) with bromonitol and kasugamycin, and surprisingly, it was found that, under certain mass ratios, it has excellent control effects against bacterial diseases, especially showing a significant synergistic effect against bacterial angular leaf spot of cucumber. Summary of the Invention

[0004] Based on the above, the purpose of this invention is to provide a bactericidal composition and its application. This bactericidal composition, through the compounding of different active ingredients, effectively reduces production costs. This bactericidal composition can be used to prevent and control bacterial diseases with excellent control effects, reducing the amount of pesticide used while delaying the development and progression of drug resistance in pathogenic bacteria.

[0005] To achieve the above objectives, the present invention adopts the following technical solution: a bactericidal composition, wherein the bactericidal composition comprises active ingredient A and active ingredient B, wherein active ingredient A is a compound of formula (I), with the following chemical structural formula: The active ingredient B is either bromonitol or kasugamycin;

[0006] Furthermore, the mass ratio of active ingredient A to active ingredient B is any value within the range of 1:24 to 60:1 or higher;

[0007] When the active ingredient B is bromonitrol

[0008] Furthermore, the mass ratio of active ingredient A to active ingredient B is 1:24 to 32:1;

[0009] Further, the mass ratio of active ingredient A to active ingredient B is 1:24, 1:12, 1:4, 1:1, 4:1, 8:1, 21:1, or 32:1;

[0010] Furthermore, the mass ratio of active ingredient A to active ingredient B is 1:12 to 32:1;

[0011] Furthermore, the mass ratio of active ingredient A to active ingredient B is 1:12, 1:4, 1:1, 4:1, 8:1, 21:1, or 32:1;

[0012] When the active ingredient B is kasugamycin

[0013] Furthermore, the mass ratio of active ingredient A to active ingredient B is 1:28 to 36:1;

[0014] Further, the mass ratio of active ingredient A to active ingredient B is 1:28, 1:14, 1:7, 2:1, 8:1, 15:1, 28:1, or 36:1;

[0015] Furthermore, the mass ratio of active ingredient A to active ingredient B is 1:14 to 28:1;

[0016] Furthermore, the mass ratio of active ingredient A to active ingredient B is 1:14, 1:7, 2:1, 8:1, 15:1, or 28:1;

[0017] Furthermore, based on a total weight of 100 wt% for the bactericidal composition, the sum of the contents of active ingredient A and active ingredient B in the bactericidal composition is 1 to 80 wt%, or any value within the above range.

[0018] Furthermore, based on a total weight of 100 wt% for the bactericidal composition, the sum of the contents of active ingredient A and active ingredient B in the bactericidal composition is 2 to 50 wt%, or any value within the above range.

[0019] Furthermore, the bactericidal composition includes agriculturally acceptable auxiliary ingredients in addition to the active ingredients;

[0020] Furthermore, the auxiliary components include one or more of the following: wetting agents, dispersants, emulsifiers, thickeners, disintegrants, antifreeze agents, defoamers, solvents, stabilizers, film-forming agents, warning colors, penetrants, and carriers;

[0021] Furthermore, the wetting agent is selected from one or more of the following: sodium dodecylbenzene sulfate, sodium dodecylbenzene sulfonate, soapberry powder, alkyl sulfate, pull-apart powder BX, silkworm excrement, alkylphenol polyoxyethylene ether, fatty alcohol polyoxyethylene ether, alkanolamide polyoxyethylene ether and its phosphate or sulfate salts, alkyl polyoxyethylene ether succinate sulfonate.

[0022] Furthermore, the dispersant is selected from one or more of the following: polycarboxylate, lignin sulfonate, naphthalene or alkylnaphthalene formaldehyde condensate sulfonate, calcium alkylbenzene sulfonate, alkylphenol polyoxyethylene phosphate, fatty alcohol polyoxyethylene polyoxypropylene ether, fatty alcohol polyoxypropylene polyoxypropylene ether, and polymeric alkyl aryl sulfonate.

[0023] Furthermore, the emulsifier is selected from one or more of the following: fatty alcohol polyoxyethylene ether, fatty alcohol ethylene oxide-propylene oxide copolymer, phenethylphenol polyoxyethylene polyoxypropylene ether, alkylphenol polyoxyethylene ether, fatty amine polyoxyethylene ether, alkylbenzene sulfonate, styrene-phenol polyoxyethylene ether, and fatty acid polyoxyethylene ester.

[0024] Furthermore, the thickener is selected from one or more of xanthan gum, polyvinyl alcohol, organobentonite, magnesium aluminum silicate, and carboxymethyl cellulose;

[0025] Furthermore, the disintegrant is selected from one or more of the following: aluminum chloride, bentonite, sucrose, modified starch, cellulose, urea, sodium carbonate, sodium bicarbonate, sodium chloride, sodium sulfate, citric acid, and tartaric acid.

[0026] Furthermore, the antifreeze is selected from one or more of alcohols, alcohol ethers, and inorganic salts, and is a mixture thereof;

[0027] Furthermore, the defoamer is selected from silicone oil, C 10 ~C 20 Saturated fatty acid compounds, C8-C 10 A mixture of one or more of fatty alcohols or silicone compounds;

[0028] Furthermore, the solvent is selected from one or more of the following: benzene, toluene, xylene, methanol, ethanol, isopropanol, n-butanol, diesel oil, N,N-dimethylformamide, cyclohexanone, ethyl acetate, N-methylpyrrolidone, propanol, butanol, ethylene glycol, diethylene glycol, ethylene glycol methyl ether, butyl ether, solvent oil, vegetable oil, vegetable oil derivatives, and deionized water;

[0029] Furthermore, the preservative is selected from one or more of the following: sorbic acid, sodium sorbate, potassium sorbate, benzoic acid, sodium benzoate, sodium p-hydroxybenzoate, and methyl p-hydroxybenzoate;

[0030] Furthermore, the stabilizer is selected from one or more of oxalic acid, succinic acid, adipic acid, borax, and epoxidized vegetable oil;

[0031] Furthermore, the warning color is selected from any one or more of the following adjustment colors: blue, green, red, purple, and yellow.

[0032] Furthermore, the film-forming agent is selected from one or more of sodium carboxymethyl starch, sodium carboxymethyl cellulose, sodium alginate, polyvinyl alcohol, and polyacrylic acid;

[0033] Furthermore, the carrier is selected from one or more of the following: kaolin, bentonite, attapulgite, light calcium carbonate, diatomaceous earth, and precipitated silica.

[0034] Furthermore, the bactericidal composition can be prepared into any formulation permitted in agriculture, wherein the formulation is a solid formulation, a liquid formulation, or a seed treatment formulation;

[0035] Furthermore, the solid formulation is a wettable powder or a water-dispersible granule; the liquid formulation is a suspension, emulsifiable concentrate, water emulsion, or microemulsion; and the seed treatment formulation is a seed treatment suspension.

[0036] A method for preventing or controlling plant pathogens from infecting plants, comprising using the bactericidal composition to control pathogens in agricultural, forestry, or horticultural plants;

[0037] Furthermore, the pathogenic bacterium is a bacterial disease caused by *Pseudomonas syringae* pv. *lachrymans*.

[0038] Furthermore, the bactericidal composition is applied in an effective amount to plant pathogens and / or their environment, or to plants, plant propagation material and subsequently grown plant organs, soil or cultivation medium, material or space.

[0039] The present invention has the following advantages over the prior art:

[0040] 1) The bactericidal composition of the present invention has high safety and is suitable for all growth stages of crops;

[0041] 2) The bactericidal composition of the present invention has high bactericidal efficiency and significant synergistic effect under certain mass ratios;

[0042] 3) The bactericidal composition of the present invention has a unique mechanism of action and can effectively protect against resistant pathogens. Detailed Implementation

[0043] To better illustrate the effective control effect of the present invention, the agents described in the above embodiments are used. To make the technical solution, objectives, and advantages of the present invention clearer, the present invention is illustrated with the following specific embodiments, but the present invention is not limited to these examples. The technical effect tests of the present invention employ a combination of indoor bioassays and field trials.

[0044] Preparation Examples

[0045] Preparation Example 1: 35% formula (I) compound·bromonitrile wettable powder (28:7)

[0046] Formula composition: by weight percentage, 28% of compound (I), 7% bromonitro alcohol, 7.7% sodium lignosulfonate, 4% calcium dodecylbenzenesulfonate, 12% kaolin, and bentonite to make up the balance.

[0047] Preparation method: According to the formula ratio, the active ingredients, dispersant, wetting agent and filler are mixed and stirred evenly in a stirring tank. The mixture is then pulverized and mixed evenly multiple times by an air jet mill to prepare the wettable powder product of the composition of the present invention.

[0048] Preparation Example 2: 45% of formula (I) compound·bromonitrile water-dispersible granules (25:20)

[0049] Formula composition: by weight percentage, 25% of compound (I), 20% of bromonitro alcohol, 8% of lignin sulfonate, 5% sodium dodecylbenzene sulfonate, 3% sodium dodecyl sulfate, 5% silica, and kaolin to make up the balance.

[0050] Preparation method: According to the formulation ratio of the example, the active ingredient compound (I) and bromonitol are added to the carrier, and surfactants and other functional additives are added thereto. After mixing, the mixture is pulverized by air jet and 10-25% water is added. Then, the mixture is kneaded, granulated, dried and sieved to obtain a water-dispersible granule product; or the pulverized powder is sprayed with water, granulated and dried in a fluidized bed granulator, and then sieved to obtain a water-dispersible granule product.

[0051] Preparation Example 3: 30% of Formula (I) compound·bromonitrile soluble solvent (12:18)

[0052] Formula composition: by weight percentage, 12% of compound (I), 18% bromonitrophenol, 3.5% alkylphenol polyoxyethylene ether, 0.3% polyvinyl alcohol 1799, 3.8% glycerol, 0.05% defoamer SAF, and deionized water to make up the balance.

[0053] Preparation method: Add the active ingredient to a certain amount of deionized water and stir thoroughly until completely dissolved. Then add surfactants, thickeners, antifreeze and other additives in sequence, stir evenly and then add an appropriate amount of defoamer to prepare a soluble product.

[0054] Preparation Example 4: 20% Compound (I)·Kasugamycin Suspension (15:5)

[0055] Formula composition: by weight percentage, 15% of compound (I), 5% kasugamycin, 1.5% alkylphenol polyoxyethylene ether, 1% naphthalene sulfonate formaldehyde condensate, 3% alkylphenol polyoxyethylene ether phosphate, 0.2% xanthan gum, 1% magnesium aluminum silicate, 4% ethylene glycol, 0.2% sodium benzoate, 0.5% silicone oil, and deionized water to make up the balance;

[0056] Preparation method: According to the formula ratio, the active ingredients, surfactants and other functional additives are placed in the reaction vessel in sequence, water is added and mixed evenly, and then subjected to high-speed shearing, wet sand milling and finally homogenization filtration to obtain the suspension product.

[0057] Preparation Example 5: 22% kasugamycin soluble concentrate of formula (I) (18:4)

[0058] Formula composition: by weight percentage, 18% of compound (I), 4% kasugamycin, 3% alkylphenol polyoxyethylene ether, 0.3% polyvinyl alcohol 1799, 3% glycerol, 0.05% defoamer SAF, and deionized water to make up the balance;

[0059] Preparation method: Add the active ingredient to a certain amount of deionized water and stir thoroughly until completely dissolved. Then add surfactants, thickeners, antifreeze and other additives in sequence, stir evenly and then add an appropriate amount of defoamer to prepare a soluble product.

[0060] Indoor activity test

[0061] Example 1:

[0062] Test Basis: The test was conducted in accordance with NY / T 1156.6-2006 "Guidelines for Indoor Bioassay Tests of Pesticides", Part 6: Determination of Combined Effects of Mixtures;

[0063] NY / T 1156.16-2008 "Guidelines for Indoor Bioassay Tests of Pesticides" - Fungicides - Part 16: Test for Inhibition of Bacterial Growth - Turbidity Method

[0064] Pathogen: Pseudomonas syringae pv. lachrymans, the pathogen of bacterial angular leaf spot of cucumber, was collected from cucumber leaves with bacterial angular leaf spot in Xiazhuang Street, Chengyang District, Qingdao City, Shandong Province. It was isolated by in vitro diseased tissue isolation method, identified by re-inoculation according to Koch's postulates, purified, inoculated onto NA solid medium and stored in a refrigerator at 4°C.

[0065] Chemical treatment: The drug solution was quantitatively added to sterilized and cooled NB medium at the concentration designed for the experiment. Each treatment was repeated four times, with a blank control consisting only of solvent and surfactant without the active ingredient. The bacterial strain grown on NA medium slant was diluted with sterile water to a concentration of 1×10⁻⁶. 7 A suspension with a concentration of 1 spore / mL was inoculated into each treatment medium with 100 μL of bacterial solution, and cultured at 28°C with shaking (120 r / min).

[0066] Experimental investigation: The turbidity of each treatment was measured before the start of cultivation. When the control treatment reached the logarithmic growth phase, the turbidity of each treatment was measured and recorded.

[0067] The prevention and control effect is calculated using the following formula.

[0068]

[0069] In the formula:

[0070] P – Growth inhibition rate, in %;

[0071] A0 – Increase in turbidity in the blank control;

[0072] A1 – Increase in turbidity after chemical treatment.

[0073] The EC50 of each pesticide was calculated using regression analysis of the logarithmic values ​​of pesticide concentrations and the probability of efficacy values ​​using a DPS (Data Processing System). 50 EC 90 Equivalent values ​​and their 95% confidence limits were determined, and significance analysis was performed on the differences between the various drug treatments.

[0074] The co-toxicity coefficient (CTC) of the mixture was calculated using Sun Yunpei's method to evaluate the type of combined effects.

[0075] A CTC ≥ 120 indicates a synergistic effect, a CTC ≤ 80 indicates an antagonistic effect, and a CTC between 80 and 120 indicates an additive effect.

[0076] The co-toxicity coefficient (CTC value) of the mixture is calculated using the following formula:

[0077]

[0078] In the formula:

[0079] ATI – Actual Measured Toxicity Index of Mixtures;

[0080] S – EC of standard bactericides 50 The unit is milligrams per liter (mg / L);

[0081] M – EC of the mixture 50 The unit is milligrams per liter (mg / L).

[0082] TTI = TI A *P A +TI B *P B

[0083] In the formula:

[0084] TTI – Theoretical Toxicity Index of Mixtures;

[0085] TI A —A. Toxicity index of drug A;

[0086] P A —Percentage content of drug A in the mixture, expressed as percentage (%);

[0087] TI B —Toxicity index of drug B;

[0088] P B —Percentage content of agent B in the mixture, expressed as percentage (%).

[0089]

[0090] In the formula:

[0091] CTC – Cotoxicity Coefficient;

[0092] ATI – Actual Measured Toxicity Index of Mixtures;

[0093] TTI – Theoretical Toxicity Index of Mixtures.

[0094] Experimental results:

[0095] Compound (I), bromonitol, and kasugamycin, as single agents, exhibited good inhibitory effects against the pathogen of bacterial angular leaf spot in cucumber. As shown in Table 1, the combination of compound (I) and bromonitol showed good antibacterial activity against bacterial angular leaf spot in cucumber. When the mass ratio of compound (I) to bromonitol was between 1:24 and 60:1, the co-toxicity coefficient was greater than 80, indicating an additive or synergistic effect. When the mass ratio was between 1:24 and 32:1, the co-toxicity coefficient was greater than 120, showing a synergistic effect. When the mass ratio was between 1:12 and 32:1, the co-toxicity coefficient was greater than 140, indicating a significant synergistic effect. When the mass ratio was 4:1, the co-toxicity coefficient was the highest at 251.847, indicating the most significant synergistic effect.

[0096] Table 1 shows the results of the indoor combined effect test of compound (I) with bronitroglycerin on bacterial keratosis.

[0097]

[0098]

[0099] As shown in Table 2, the combination of compound (I) and kasugamycin exhibited good antibacterial activity against bacterial angular leaf spot in cucumber. When the mass ratio of compound (I) to kasugamycin was between 1:28 and 36:1, the co-toxicity coefficient was greater than 120, indicating a synergistic effect. When the mass ratio of compound (I) to kasugamycin was between 1:14 and 36:1, the co-toxicity coefficient was greater than 140, showing a significant synergistic effect. When the mass ratio of compound (I) to kasugamycin was 8:1, the co-toxicity coefficient was the highest at 241.914, indicating the most significant synergistic effect.

[0100] Table 2 shows the results of the indoor combined treatment of compound (I) with kasugamycin for bacterial keratosis.

[0101]

[0102] Field efficacy trials

[0103] Field efficacy trial of herbicides for bacterial angular leaf spot of cucumber

[0104] Test crop: cucumber

[0105] Test subject: Bacterial keratosis (Pseudomonas syringae pv. lachrymans)

[0106] Test location: Arched insulated vegetable greenhouse in Qingzhou, Weifang City, Shandong Province.

[0107] Application dates: April 24 and May 15, 2023, for a total of two applications. The weather was favorable during the trial period.

[0108] Experimental field conditions: The experimental field had moderate soil fertility, flat terrain, uniform fertility, and good irrigation conditions. All experimental plots had uniform cultivation conditions (soil type, fertilization, tillage, row spacing, etc.) and were consistent with local Good Agricultural Practices (GAP).

[0109] Disease incidence in the experimental field: At the beginning of the experiment, sporadic ulcer lesions were visible on the leaves of the plants.

[0110] Experimental treatments: Each treatment was arranged in a randomized block design with buffer rows between adjacent blocks, and the results were repeated 4 times, with each treatment lasting 20 minutes. 2 The specific experimental treatments and dosages are as follows:

[0111] Table 3. Experimental treatments and drug dosages

[0112] medicine <![CDATA[Active ingredient application rate (a.i g / hm 2 )]]> 30% of Formula (I) compound·bromonitrile soluble solvent (12:18) 225 22% Compound (I) Kasugamycin Soluble Solution (18:4) 110 25% Bromonitrocellulose Water Dispersible Granules 150 6% Kasugamycin Soluble Solution 60 20% Bifemetstrobin water dispersible granules 150 Water comparison /

[0113] Survey method: Five random sampling points were taken from each plot, and all leaves of three plants were investigated at each point. The disease was classified according to the percentage of diseased area on the leaves to the total leaf area. The disease index and control effect were calculated. The data were analyzed for significance using Duncan's multiple range test.

[0114] The specific grading standards are as follows:

[0115] Grade 0: No lesions;

[0116] Grade 1: Lesions cover 5% or less of the total leaf area;

[0117] Grade 3: The lesion area accounts for 6% to 10% of the total leaf area;

[0118] Level 5: The lesion area accounts for 11% to 20% of the total leaf area;

[0119] Level 7: Lesions cover 21% to 50% of the total leaf area;

[0120] Level 9: The lesion area accounts for more than 51% of the total leaf area.

[0121] Investigation time and frequency: The baseline of the disease was investigated before medication, and investigated again on 7 days and 14 days after the last medication.

[0122] The efficacy of the drug is calculated using the following formula:

[0123]

[0124] During the experiment, cucumbers in all treatment plots grew well, and no pesticide damage was observed in any treatment.

[0125] The results of the field efficacy trials are shown in the table below:

[0126] The analysis of the field efficacy test results in the table above shows that Bifemetstrobin, when combined with bromonitol and kasugamycin, has a good control effect on bacterial angular leaf spot of cucumber. As shown in Table 4, 7 days after the last application, the control efficacy of 30% compound (I)·bromonitol soluble concentrate (12:18) and 22% compound (I)·kasugamycin soluble concentrate (18:4) against bacterial angular leaf spot of cucumber were 85.31% and 84.11%, respectively.

[0127] Table 4. Field efficacy test results of each treatment against bacterial angular leaf spot of cucumber (7 days after the last application).

[0128]

[0129] As shown in Table 5, 7 days after the last application, the control efficacy of 30% compound (I)·bromonidol soluble concentrate (12:18) and 22% compound (I)·kasugamycin soluble concentrate (18:4) against bacterial angular leaf spot of cucumber was 86.88% and 87.46%, respectively.

[0130] Table 5. Field efficacy test results of each treatment against bacterial angular leaf spot of cucumber (14 days after the last application).

[0131]

[0132] In summary, through indoor toxicity testing and field efficacy trials, it can be seen that the Bifemetstrobin fungicidal composition of the present invention has a good control effect on plant pathogens, is safe for target crops, and has significant efficacy. It is superior to single agents in delaying the development of drug resistance and prolonging the duration of action, and can effectively reduce costs and reduce pesticide residues.

[0133] Although this application describes specific embodiments in detail with the aid of examples, the disclosure of this application can be modified and substituted in various ways. However, it should be understood that the disclosure of this application is not limited to the specific form disclosed. Rather, the disclosure of this application covers all modifications, equivalents, and substitutions within the scope of the disclosure of this application, the scope of which is defined by the appended claims and their legal equivalents.

Claims

1. A fungicidal composition, characterized by, The bactericidal composition comprises active ingredient A and active ingredient B, wherein active ingredient A is a compound of formula (I). Chemical structural formula: (I) The active ingredient B is either bromonitol or kasugamycin, the mass ratio of the compound shown in formula (I) to bromonitol is 1:24 to 32:1, and the mass ratio of the compound shown in formula (I) to kasugamycin is 1:28 to 36:

1.

2. The bactericidal composition according to claim 1, characterized by, The mass ratio of the compound shown in formula (I) to bromonitol is 1:12 to 32:1, and the mass ratio of the compound shown in formula (I) to kasugamycin is 1:14 to 28:

1.

3. The germicidal composition according to claim 1, wherein The mass ratio of the compound shown in formula (I) to bromonitol is 1:24, 1:12, 1:4, 1:1, 4:1, 8:1, 21:1, 32:1, and the mass ratio of the compound shown in formula (I) to kasugamycin is 1:28, 1:14, 1:7, 2:1, 8:1, 15:1, 28:1, 36:

1.

4. The germicidal composition according to claim 1, wherein The total weight of the bactericidal composition is 100 wt%, and the sum of the contents of active ingredient A and active ingredient B in the bactericidal composition is 1 to 80 wt%.

5. The fungicidal composition according to claim 4, characterized in that, The total weight of the bactericidal composition is 100 wt%, and the sum of the contents of active ingredient A and active ingredient B in the bactericidal composition is 2 to 50 wt%.

6. The germicidal composition according to claim 1, wherein In addition to the active ingredient, the bactericidal composition also includes auxiliary components, which include one or more of the following: wetting agents, dispersants, emulsifiers, thickeners, disintegrants, antifreeze agents, defoamers, solvents, stabilizers, film-forming agents, warning colors, penetrants, and carriers.

7. The germicidal composition according to claim 1, wherein The bactericidal composition is prepared into formulations such as wettable powder, water-dispersible granules, suspension concentrate, emulsifiable concentrate, water-in-oil emulsion, microemulsion, and seed treatment suspension.

8. A method of controlling or preventing infestation of a plant by a plant pathogen, characterized by, The bactericidal composition of claim 1 is used to prevent and control pathogens in agricultural, forestry, or horticultural plants, wherein the pathogen is a bacterial disease caused by *Pseudomonas syringae*, a pathogenic species of cucumber.

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