Bactericidal composition containing isoprofluopicolide and methoxyl acrylate and application thereof
By reasonably combining isopropyramide and methoxyacrylate bactericides and adding auxiliary materials, it is prepared into a bactericidal composition, which solves the problem of insufficient resistance to pathogenic bacteria and bactericidal efficiency, achieves high-efficiency, low-toxicity, and broad-spectrum bactericidal effects, and promotes the sustainable development of agricultural production.
Patent Information
- Application Number
- CN202510323407.6
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2025-03-19
- Publication Date
- 2025-06-20
AI Technical Summary
The prior art is difficult to effectively prevent and treat pathogenic bacteria when the disease is prevented and cured, and the use efficiency and safety of fungicides are insufficient, which affects the sustainable development of agricultural production.
By reasonably combining isopropyramidine and methoxyacrylate bactericides, and adding dispersants, wetting agents and other auxiliary materials, a bactericidal composition containing isopropyramidine and methoxyacrylate is prepared to prevent and treat crop diseases.
The bactericidal composition has strong polarity and hydrogen bond formation ability, and is difficult to produce drug resistance. The drug is highly stable, selective toxicity is significant, and the broad-spectrum bactericidal effect is significant, which delays the generation of disease resistance.
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Figure BDA0005318055620000061
Abstract
Description
Technical Field
[0001] The present invention relates to the technical field of pesticides, and specifically to a bactericidal composition containing isoflucypram and methoxyacrylates and its application. Background Art
[0002] Isoflucypram is a novel pyrazole amide fungicide. As a new generation of SDHI fungicides, isoflucypram has a novel chemical structure. A cyclopropyl group is introduced into the amide bond part of its molecule. Among the previous fungicides of the same kind, only fluxapyroxad introduced a substituent into the amide bond part, which also makes its performance greatly improved compared with other SDHI fungicides. Its structural formula is shown as follows:
[0003]
[0004] Currently, isoflucypram has been developed for controlling fungal diseases in cereal fields, such as barley net blotch, leaf spot, leaf rust, wheat stripe rust, leaf rust, leaf blight, rye stripe rust and leaf rust, etc. It has the characteristics of broad spectrum, high efficiency, low dosage, long residual period, and promoting cereal yield increase.
[0005] Methoxyacrylate fungicides are a class of fungicides with low toxicity, high activity, broad spectrum and systemic properties. They have protective, therapeutic and eradicative effects. They have good activity against Ascomycetes, Basidiomycetes, Oomycetes, etc., and can effectively control pathogenic bacteria resistant to other fungicides.
[0006] In the actual process of agricultural production, the most likely problem in controlling diseases is the resistance of pathogenic bacteria. Mixing different varieties of ingredients is a common method for controlling resistant diseases. Therefore, it is of great significance for the sustainable development of agriculture to study a bactericidal composition that can expand the scope of disease control, delay the generation of disease resistance, and at the same time have high efficiency and low toxicity. Summary of the Invention
[0007] In view of the deficiencies of the prior art, the present invention provides a bactericidal composition containing isoflucypram and methoxyacrylates and its application.
[0008] To achieve the above objectives, the present invention is realized through the following technical solutions:
[0009] The bactericidal composition containing isoflucypram and methoxyacrylates includes active ingredients and excipients. The mass percentage content of the active ingredients is 30 - 70%, and the rest is excipients;
[0010] The active ingredients are isoflucypram and methoxyacrylate fungicides, and the mass ratio of isoflucypram to methoxyacrylate fungicides is 20 - 80:1 - 30.
[0011] Preferably, the mass ratio of isopropylfluopyram to the strobilurin fungicide is 40 - 60:10 - 20.
[0012] More preferably, the mass ratio of isopropylfluopyram to the strobilurin fungicide is 50:15.
[0013] Preferably, the strobilurin fungicide is one or more of kresoxim-methyl, azoxystrobin, pyraclostrobin, trifloxystrobin, picoxystrobin, fluoxastrobin, and metominostrobin.
[0014] Preferably, the auxiliary materials include the following raw materials in parts by weight: 1 - 15 parts by weight of lignin carboxylate pesticide (CMBL) dispersant, 1 - 10 parts by weight of K12 - B wetting agent, and 0 - 20 parts by weight of filler kaolin.
[0015] Preferably, the herbicidal composition is mixed with common auxiliary materials for pesticides to prepare any preparation suitable for agricultural use, and the preparation is one or more of water - dispersible granules, wettable powders, granules, suspensions, and microemulsions.
[0016] Preferably, the preparation method of the composition containing isopropylfluopyram and strobilurin is as follows:
[0017] S1: Add the dispersant and wetting agent to water, stir and mix evenly to prepare a mixed solution;
[0018] S2: Add the fungicide containing isopropylfluopyram and strobilurin and the filler to the mixed solution, and homogenize and disperse with a homogenizer for 20 - 40 min;
[0019] S3: After dispersion, grind with a colloid mill and grind with a sand mill until the particle size of the material ≤ 5 μm;
[0020] S4: After grinding, use a pressure - type spray dryer, heat up to 130 - 150 °C, and spray - dry to obtain the bactericidal composition containing isopropylfluopyram and strobilurin.
[0021] Preferably, the bactericidal composition is used to control crop diseases, and the crop diseases include downy mildew (cucumber downy mildew), late blight, damping - off, Phytophthora root rot, powdery mildew (wheat powdery mildew), rust, leaf spot (tomato early blight), rice blast (rice rice blast), anthracnose (cucumber anthracnose).
[0022] The beneficial effects of the present invention:
[0023] The present invention uses isoflucypram and a bactericide of the strobilurin class to form an effective ingredient through reasonable compounding, and then dispersants, wetting agents and other auxiliaries are added and mixed evenly to prepare a bactericidal composition containing isoflucypram and a strobilurin class.
[0024] The bactericidal composition containing isoflucypram and a strobilurin class prepared by the present invention has strong polarity and hydrogen bond formation ability. This strong binding makes it more difficult for pathogens or cells to develop drug resistance through target mutations. At the same time, the drug is more stable and not easily degraded by the enzymes of pathogens, and its unique spatial configuration reduces the adaptability of drug-resistant mutants, putting drug-resistant strains at a disadvantage in competition.
[0025] The bactericidal composition containing isoflucypram and a strobilurin class prepared by the present invention has a fluorinated group, and the fluorine atom in the fluorinated group has a strong electron-withdrawing effect, which can improve the molecular stability, interfere with the active efflux of the agent by pathogens at the same time, improve the high efficiency of the agent, and delay drug resistance.
[0026] The bactericidal composition containing isoflucypram and a strobilurin class prepared by the present invention has more bactericidal groups such as a strobilurin group and a pyridinecarboxamide group. The pyridinecarboxamide group can bind to specific sites of β-tubulin of pathogens, inhibit tubulin polymerization, disrupt the assembly of the cytoskeleton, resulting in the arrest of hyphal growth and the inhibition of spore germination. At the same time, this group has a high affinity for the tubulin of oomycetes, but has little effect on the microtubule systems of plants and mammals, reflecting selective toxicity; the strobilurin group blocks energy metabolism by inhibiting the cellular respiration in the mitochondria of pathogens, ultimately leading to the death of pathogens. The two are combined through a pyridine group to enhance the synergistic bactericidal effect and improve the bactericidal spectrum. Detailed implementation mode
[0027] Next, the technical solutions in the embodiments of the present invention will be clearly and completely described in conjunction with the embodiments of the present invention. Obviously, the described embodiments are only a part of the embodiments of the present invention, rather than all the embodiments. All other embodiments obtained by those of ordinary skill in the art based on the embodiments of the present invention without making creative efforts fall within the scope of protection of the present invention.
[0028] The dispersant is a lignin carboxylate pesticide (CMBL) dispersant;
[0029] The wetting agent is: 1-10 parts by weight of K12-B wetting agent;
[0030] The filler is kaolin.
[0031] Example 1
[0032] S1: Add 10 parts by weight of a dispersant and 10 parts by weight of a wetting agent to water, stir and mix evenly to prepare a mixed solution.
[0033] S2: Add 50 parts by weight of isoflucypram and 15 parts by weight of a bactericide of the methoxyacrylate type and 10 parts by weight of a filler to the mixed solution, and homogenize and disperse with a homogenizer for 20 min.
[0034] S3: After dispersion, pulverize with a colloid mill and grind with a sand mill until the particle size of the material ≤ 5 μm.
[0035] S4: After grinding, use a pressure spray dryer, heat up to 130 °C, and spray dry to obtain a bactericidal composition containing isoflucypram and methoxyacrylate.
[0036] Example 2
[0037] S1: Add 15 parts by weight of a dispersant and 5 parts by weight of a wetting agent to water, stir and mix evenly to prepare a mixed solution.
[0038] S2: Add 50 parts by weight of isoflucypram and 15 parts by weight of a bactericide of the methoxyacrylate type and 20 parts by weight of a filler to the mixed solution, and homogenize and disperse with a homogenizer for 20 min.
[0039] S3: After dispersion, pulverize with a colloid mill and grind with a sand mill until the particle size of the material ≤ 5 μm.
[0040] S4: After grinding, use a pressure spray dryer, heat up to 150 °C, and spray dry to obtain a bactericidal composition containing isoflucypram and methoxyacrylate.
[0041] Example 3
[0042] S1: Add 15 parts by weight of a dispersant and 5 parts by weight of a wetting agent to water, stir and mix evenly to prepare a mixed solution.
[0043] S2: Add 50 parts by weight of isoflucypram and 15 parts by weight of a bactericide of the methoxyacrylate type and 20 parts by weight of a filler to the mixed solution, and homogenize and disperse with a homogenizer for 20 min.
[0044] S3: After dispersion, pulverize with a colloid mill and grind with a sand mill until the particle size of the material ≤ 5 μm.
[0045] S4: After grinding, use a pressure spray dryer, heat up to 150 °C, and spray dry to obtain a bactericidal composition containing isoflucypram and methoxyacrylate.
[0046] Comparative Example 1
[0047] The difference between this comparative example and Example 1 is that the mixed solution of isoflucypram and strobilurin fungicides is replaced with pure isoflucypram.
[0048] Comparative Example 2
[0049] The difference between this comparative example and Example 1 is that the mixed solution of isoflucypram and strobilurin fungicides is replaced with pure strobilurin fungicides.
[0050] Detection of mycelial growth inhibition
[0051] 1. Preparation of stock solution: Weigh 50 mg of the bactericidal compositions of Examples 1 - 3 and Comparative Examples 1 - 2 respectively with a ten-thousandth electronic balance, add them into 10 ml centrifuge tubes, and make marks. Prepare a stock solution of 104 μg / mL with 5 ml of DMSO solution. Under ultra-clean and sterile conditions, dilute the prepared 104 μg / mL stock solution with PDA medium into a 50 μg / mL toxic medium plate, and set a blank control for the experiment.
[0052] 2. Preparation of PDA medium: Wash the potatoes, peel them, cut them into small pieces, wrap them with double-layer gauze, bring deionized water to a boil, cook for 25 - 35 min, take them out, add agar strips soaked in cold water, stir and dissolve for 30 - 40 min, add glucose, stir evenly, make up the volume with water, seal and wrap, and sterilize at high temperature.
[0053] 3. Test method: According to NY / T 1156.2 - 2006, use the mycelial growth rate method for detection. On the ultra-clean workbench, punch holes with a puncher with a diameter of 5 mm, cut out the mycelial discs, inoculate the mycelial discs in the center of the cooled culture dishes containing the drug, cover the dish lids, and incubate them in an inverted 25 °C incubator.
[0054] 4. Calculation
[0055] After the diameter of the CK reaches 6 - 8 cm, measure the diameter of each treated colony by the cross method, calculate the colony growth diameter using the formula, and take its average value.
[0056] Colony growth diameter = colony diameter - mycelial disc diameter
[0057] For the measurement results, calculate the mycelial growth inhibition rate of each compound against the pathogen based on the colony growth diameter of the blank control and the colony growth diameter of the colonies treated with the agent, referring to the following formula:
[0058]
[0059] Table 1 Mycelial growth inhibition rate (%) of each example and comparative example
[0060] Rice blast Early blight of tomato Downy mildew of cucumber Anthracnose of cucumber Example 1 46.97 89.57 74.51 64.20 Example 2 60.61 92.36 79.74 72.16 Example 3 56.06 90.19 78.43 65.98 Comparative example 1 12.36 15.63 60.28 18.36 Comparative example 2 54.68 90.23 10.68 85.25
[0061] As can be seen from Table 1, in Examples 1-3, as the content of the fungicide containing isopropylfluopyram and methoxyacrylate increases, the fungicidal effect is better. Comparing Examples 1-3 with Comparative Example 1, it can be seen that the mycelial elongation inhibition rate in the examples is higher. The reason is that Examples 1-3 contain more fungicidal groups, such as methoxyacrylate groups. The methoxyacrylate group blocks energy metabolism by inhibiting cell respiration in the mitochondria of pathogenic bacteria, ultimately leading to the death of pathogenic bacteria, thereby improving its fungicidal efficiency. The pyridinecarboxamide group can bind to specific sites of β-tubulin in pathogenic bacteria, inhibit tubulin polymerization, disrupt the assembly of the cytoskeleton, resulting in the arrest of mycelial growth and the inhibition of spore germination. At the same time, this group has a high affinity for the tubulin of oomycetes, while having little effect on the microtubule systems of plants and mammals, reflecting selective toxicity. By comparing Example 1 with Comparative Example 2, it can be seen that the present invention has a wider scope of action compared to single-variety fungicides.
[0062] Resistance detection
[0063] The resistance of wheat powdery mildew was detected by the method of in vitro spraying.
[0064] 1. Preparation of stock solution: 0.01 g of the fungicidal compositions of Examples 1-3 and Comparative Examples 1-2 were respectively taken, dissolved in 1 ml of acetone, and deionized water was added to prepare a 200 mg·L-1 stock solution.
[0065] 2. The stock solution was gradually diluted into a series of concentrations of 100, 50, 25, 12.5, 6.25 mg·L-1 of the liquid medicine, and repeated three times.
[0066] The sensitive baseline EC50 of wheat powdery mildew to methoxyacrylate fungicides is 0.1-0.5 mg·L-1. Taking the sensitive baseline EC50 of azoxystrobin as 0.43 mg·L-1 as a reference, the resistance level (RF) is the ratio of the EC50 of the tested strain to the sensitive baseline EC50. The resistance classification standard: RF ≤ 5, sensitive; 5 < RF ≤ 10, low resistance; 10 < RF ≤ 40, medium resistance; RF > 40, high resistance.
[0067] Table 2 Detection results of the sensitivity of wheat powdery mildew to each example and comparative example
[0068]
[0069] The lower the resistance level, the higher its sensitivity. As can be seen from Table 2, the resistance levels of Examples 1-3 are relatively low, and the wheat powdery mildew plants are more sensitive to them. The resistance levels of Comparative Examples 1-2 are relatively high, and the wheat powdery mildew plants are less sensitive to them. The reason is that Examples 1-3 contain pyridine groups. As an aromatic heterocycle, the pyridine group has strong polarity and hydrogen bond-forming ability. This strong binding makes it more difficult for pathogens or cells to develop drug resistance through target mutations. At the same time, the rigid structure of the pyridine ring may make the drug more stable and not easily degraded by the enzymes of pathogens. Moreover, its unique spatial configuration reduces the adaptability of drug-resistant mutants, putting drug-resistant strains at a disadvantage in competition.
[0070] In the description of this specification, the description referring to terms such as "one embodiment", "example", "specific example", etc. means that the specific features, structures, materials or characteristics described in connection with the embodiment or example are included in at least one embodiment or example of the present invention. In this specification, the schematic representation of the above terms does not necessarily refer to the same embodiment or example. Moreover, the specific features, structures, materials or characteristics described can be combined in a suitable manner in any one or more embodiments or examples.
[0071] The above content is only an example and explanation of the present invention. Those skilled in the art of the present technology can make various modifications or supplements to the described specific embodiments or use similar methods for substitution. As long as they do not deviate from the invention or exceed the scope defined by the claims of the present invention, they should fall within the protection scope of the present invention.
Claims
1. A fungicidal composition containing isopropyram and strobilurin, characterized in that: It comprises active ingredients and auxiliary materials, wherein the mass percentage of the active ingredients is 30-70%, and the rest is auxiliary materials; The active ingredients are isoproflupyram and methoxyacrylate fungicide, and the mass ratio of isoproflupyram to methoxyacrylate fungicide is 20-80:1-30.
2. The fungicidal composition containing isopropyram and strobilurin according to claim 1, characterized in that: The mass ratio of isopropyram to the strobilurin fungicide is 40-60:10-20.
3. The fungicidal composition containing isopropyram and strobilurin according to claim 1, characterized in that: The mass ratio of isopropyram to the strobilurin fungicide is 50:
15.
4. The fungicidal composition containing isopropyram and strobilurin according to claim 1, characterized in that: The methoxyacrylate fungicide is one or more of kresoxim-methyl, azoxystrobin, pyraclostrobin, trifloxystrobin, picoxystrobin, fluoxastrobin and fenoxystrobin.
5. The fungicidal composition containing isopropyram and strobilurin according to claim 1, characterized in that: The auxiliary materials include the following raw materials in parts by weight: 1-15 parts by weight of lignin carboxylate pesticide (CMBL) dispersant, 1-10 parts by weight of K12-B wetting agent, and 0-20 parts by weight of kaolin filler.
6. The fungicidal composition containing isopropyram and triazoles according to claim 1, characterized in that: The herbicidal composition is mixed with common auxiliary materials used in pesticides to prepare any preparation suitable for use in agriculture, and the preparation is one or more of water-dispersible granules, wettable powders, granules, suspensions, and microemulsions.
7. The fungicidal composition containing isopropyram and strobilurin according to claim 1, characterized in that: The preparation method of the composition containing isopropyram and methoxyacrylates is as follows: S1: adding a dispersant and a wetting agent into water, stirring and mixing, and preparing a mixed solution; S2: adding the fungicide containing isopropyram and methoxyacrylate and the filler into the mixed solution, and homogenizing and dispersing with a homogenizer for 20-40 minutes; S3: After dispersion, the material is crushed by colloid mill and ground by sand mill until the particle size is ≤5μm; S4: After grinding, use a pressure spray dryer to raise the temperature to 130-150° C. and spray dry to obtain a fungicide composition containing isopropyram and strobilurin.
8. Use of the fungicidal composition containing isopropyram and strobilurin according to any one of claims 1 to 7, characterized in that: The fungicide composition is used to prevent and treat crop diseases, including downy mildew (cucumber downy mildew), late blight, damping-off, phytophthora root rot, powdery mildew (wheat powdery mildew), rust, leaf spot (tomato early blight), rice blast (rice blast), and anthracnose (cucumber anthracnose).