Bactericidal composition containing isoprofluopicolide and triazole and application thereof

Abstract

The invention relates to the technical field of pesticides, and discloses a bactericidal composition containing isoprofluopicolide and triazole and application thereof.According to the bactericidal composition, isoprofluopicolide and triazole bactericides are reasonably compounded to obtain an effective component, then auxiliaries such as a dispersing agent and a wetting agent are added, uniform mixing is conducted, and the bactericidal composition containing isoprofluopicolide and triazole is obtained. The bactericidal composition containing the isoprofluopicolide and the triazoles is prepared, and the prepared bactericidal composition containing the isoprofluopicolide and the triazoles has the advantages that the drug resistance is delayed, the bactericidal broad spectrum is expanded, and the synergistic bactericidal effect is enhanced.

Description

Technical Field

[0001] The present invention relates to the technical field of pesticides, and specifically to a bactericidal composition containing isoflucypram and triazoles 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 type, 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 is 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] Triazole fungicides exert their bactericidal activity by hindering the synthesis of ergosterol in pathogenic fungi. They can interfere with the normal physiological functions of fungi, resulting in the death of the fungal cells due to damage to the cell membrane. At the same time, triazole fungicides have a broad bactericidal spectrum.

[0006] In the actual process of agricultural production, the most easily occurring problem in disease control is the retention rate of fungicides under sunlight. 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 disease control range, improve ultraviolet 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 triazoles and its application.

[0008] To achieve the above objectives, the present invention is realized through the following technical solutions:

[0009] A bactericidal composition containing isoflucypram and triazoles, including active ingredients and excipients. The mass percentage content of the active ingredients is 30 - 70%, and the remainder is excipients;

[0010] The active ingredients are a combination of isoflucypram and triazole fungicides, and the mass ratio of isoflucypram to triazole fungicides is 20 - 80:10 - 30.

[0011] Preferably, the mass ratio of isoflucypram to triazole fungicides is 40 - 60:10 - 20.

[0012] More preferably, the mass ratio of isoflucypram to triazole fungicides is 50:15.

[0013] Preferably, the triazole fungicides are one or more of tebuconazole, difenoconazole, propiconazole, epoxiconazole, myclobutanil, metconazole, triticonazole, flusilazole, prothioconazole, tetraconazole, penconazole, triadimefon, hexaconazole, flutriafol, cyproconazole, bitertanol.

[0014] Preferably, the auxiliary materials include the following raw materials in parts by weight: 10 - 20 parts by weight of lignin carboxylate pesticide (CMBL) dispersant, 2 - 3 parts by weight of K12 - B wetting agent, 0.1 - 0.3 parts by weight of C6 defoaming agent, and 0.5 - 5 parts by weight of disintegrant sodium chloride.

[0015] Preferably, the herbicidal composition is mixed with common auxiliary materials in pesticides to prepare any preparation suitable for agricultural use, and the preparations are one or more of water - dispersible granules, wettable powders, granules, suspensions, microemulsions.

[0016] Preferably, the preparation method of the composition containing isoflucypram and triazoles is as follows:

[0017] S1: Add the dispersant and wetting agent into water, stir and mix evenly to prepare a mixed solution;

[0018] S2: Add the fungicide containing isoflucypram and triazoles and filler into the mixed solution, and homogenize and disperse with a homogenizer for 20 - 40 min;

[0019] S3: After dispersion, pulverize 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 isoflucypram and triazoles.

[0021] Preferably, the bactericidal composition is used to prevent and control crop diseases, and the crop diseases include downy mildew (cucumber downy mildew), late blight, Phytophthora root rot (Pythium aphanidermatum), powdery mildew (wheat powdery mildew), rust, leaf spot (tomato early blight), anthracnose, Deuteromycetes (Fusarium moniliforme, cotton damping - off).

[0022] The beneficial effects of the present invention:

[0023] The present invention uses isoflucypram and a triazole fungicide to be rationally compounded to obtain an active ingredient, and then dispersants, wetting agents and other auxiliaries are added, and mixed evenly to prepare a bactericidal composition containing isoflucypram and triazole.

[0024] The bactericidal composition containing isoflucypram and triazole 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, and at the same time makes 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.

[0025] The bactericidal composition containing isoflucypram and triazole prepared by the present invention has a fluorinated group. 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 medicament by pathogenic bacteria, improve the high efficiency of the medicament, and delay drug resistance.

[0026] The bactericidal composition containing isoflucypram and triazole prepared by the present invention has more bactericidal groups such as methoxyacrylate group and pyridineamide group. The pyridineamide group can bind to specific sites of β-tubulin of pathogenic bacteria, inhibit the polymerization of tubulin, 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, and has little effect on the microtubule system of plants and mammals, reflecting selective toxicity; the triazole group. Triazoles block the CYP51 enzyme, so that ergosterol in the fungal cell membrane is replaced by 24-methylene dihydro lanosterol, resulting in a decrease in membrane fluidity and an increase in permeability, and finally the cell ruptures and dies, thereby improving its bactericidal efficiency. Specific Embodiments

[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. Based on the embodiments of the present invention, all other embodiments obtained by those of ordinary skill in the art without making creative efforts belong to the scope of protection of the present invention.

[0028] Example 1

[0029] S1: Add 10 parts by weight of a dispersant, 3 parts by weight of a wetting agent, and 0.1 part by weight of an antifoaming agent to water, stir and mix evenly to prepare a mixed solution.

[0030] S2: Add 50 parts by weight of isoflucypram, 15 parts by weight of a triazole fungicide, and 0.5 part by weight of a disintegrant sodium chloride to the mixed solution, and homogenize and disperse with a homogenizer for 20 min.

[0031] S3: After dispersion, it is pulverized by a colloid mill and ground by a sand mill until the particle size of the material ≤ 5 μm.

[0032] S4: After grinding, it is spray-dried with a pressure spray dryer by heating to 130 °C to obtain a bactericidal composition containing isopropylfluopyram and triazoles.

[0033] Example 2

[0034] S1: 15 parts by weight of a dispersant, 2 parts by weight of a wetting agent, and 0.2 parts by weight of an antifoaming agent are added to water and stirred evenly to prepare a mixed solution.

[0035] S2: 50 parts by weight of isopropylfluopyram, 15 parts by weight of a triazole bactericide, and 3 parts by weight of a disintegrant sodium chloride are added to the mixed solution, and homogenized and dispersed by a homogenizer for 20 min.

[0036] S3: After dispersion, it is pulverized by a colloid mill and ground by a sand mill until the particle size of the material ≤ 5 μm.

[0037] S4: After grinding, it is spray-dried with a pressure spray dryer by heating to 150 °C to obtain a bactericidal composition containing isopropylfluopyram and triazoles.

[0038] Example 3

[0039] S1: 20 parts by weight of a dispersant, 2.5 parts by weight of a wetting agent, and 0.2 parts by weight of an antifoaming agent are added to water and stirred evenly to prepare a mixed solution.

[0040] S2: 50 parts by weight of isopropylfluopyram, 15 parts by weight of a triazole bactericide, and 5 parts by weight of a disintegrant sodium chloride are added to the mixed solution, and homogenized and dispersed by a homogenizer for 20 min.

[0041] S3: After dispersion, it is pulverized by a colloid mill and ground by a sand mill until the particle size of the material ≤ 5 μm.

[0042] S4: After grinding, it is spray-dried with a pressure spray dryer by heating to 150 °C to obtain a bactericidal composition containing isopropylfluopyram and triazoles.

[0043] Comparative Example 1

[0044] The difference between this comparative example and Example 1 is that the mixed solution of isopropylfluopyram and triazole bactericide is replaced with pure isopropylfluopyram.

[0045] Comparative Example 2

[0046] The difference between this comparative example and Example 1 is that the mixed solution of isopropylfluopyram and triazole bactericide is replaced with pure triazole bactericide.

[0047] Detection of mycelial growth inhibition

[0048] 1. Preparation of mother liquor: Weigh 50 mg of the bactericidal compositions of Examples 1 - 3 and Comparative Examples 1 - 2 respectively with an electronic balance accurate to one ten - thousandth, add them into 10 - ml centrifuge tubes, and make marks. Prepare a mother liquor with a concentration of 104 μg / mL using 5 ml of DMSO solution. Under ultra - clean and sterile conditions, dilute the prepared 104 μg / mL mother liquor with PDA medium into a poisoned culture medium plate with a concentration of 50 μg / mL. A blank control is set for the experiment.

[0049] 2. Preparation of PDA medium: Wash the potatoes, peel them, cut them into small pieces, wrap them with double - layer gauze, boil deionized water, 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.

[0050] 3. Test method: According to NY / T 1156.2 - 2006, use the mycelial growth rate method for detection. On a super - clean workbench, use a punch with a diameter of 5 mm to punch holes, cut out fungal discs, inoculate the fungal 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.

[0051] 4. Calculation

[0052] After the diameter of CK reaches 6 - 8 cm, measure the diameters of each treated colony by the cross - method, calculate the colony growth diameter using the formula, and take the average value.

[0053] Colony growth diameter = Colony diameter - Fungal disc diameter

[0054] 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:

[0055]

[0056] Table 1 Mycelial growth inhibition rate of each example and comparative example (%)

[0057] Rhizoctonia solani Pythium aphanidermatum Phytophthora infestans Fusarium moniliforme Example 1 46.97 74.51 89.57 64.20 Example 2 60.61 79.74 92.36 72.16 Example 3 56.06 78.43 90.19 65.98 Comparative Example 1 53.82 48.78 40.50 35.52 Comparative Example 2 12.36 65.87 60.28 53.46

[0058] As can be seen from Table 1, in Examples 1-3, as the content of the fungicide containing isopropylfluopyram and triazoles increases, the fungicidal effect is better. By 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 triazole groups. Triazoles block the CYP51 enzyme, causing ergosterol in the fungal cell membrane to be replaced by 24-methylene dihydro lanosterol, resulting in a decrease in membrane fluidity and an increase in permeability, and ultimately cell rupture and death, thereby improving its fungicidal efficiency. The pyridine amide group can bind to specific sites of the β-tubulin of the pathogen, inhibit the polymerization of tubulin, and disrupt the assembly of the cytoskeleton, resulting in the stagnation of mycelial growth and the inhibition of spore germination. At the same time, this group has a high affinity for the tubulin of the 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 range of action compared to single-variety fungicides.

[0059] Anti-ultraviolet performance test

[0060] Prepare methanol dispersions of Examples 1-3 and Comparative Examples 1-2 with the same concentration respectively. Irradiate the prepared dispersions with an ultraviolet lamp (36W, 254nm) in a closed space. The irradiation temperature is 20-30°C, and the dispersion is magnetically stirred at a speed of 50r / min. At the beginning, samples are taken at intervals of 1-2h. As the ultraviolet irradiation time increases, the sampling time increases. The absorbance is measured at 274nm with an ultraviolet spectrophotometer.

[0061] Perform solid ultraviolet-visible absorption spectroscopy tests on Examples 1-3 and Comparative Examples 1-2. The test instrument is a UV-2600 type ultraviolet-visible diffuse reflectance spectrometer. Take 0.5g of the samples of Examples 1-3 and Comparative Examples 1-3, press them into tablets, put them into the test chamber, start the device for testing, and the test wavelength is 200-800nm.

[0062] Table 2 Anti-ultraviolet detection results of each example and Comparative Example after 100h

[0063] Retention rate (%) Example 1 37.2 Example 2 40.3 Example 3 38.6 Comparative Example 1 18.3 Comparative Example 2 18.5

[0064] In Examples 1-3, as the content of the fungicide containing isopropylfluopyram and triazoles increases, its ultraviolet resistance becomes better. Comparing Example 1 with Comparative Example 1, it can be seen that the retention rate of Example 1 is higher. The reason is that Examples 1-3 contain triazine groups. The triazine group is a highly efficient ultraviolet absorption group with high absorption performance, broad spectrum, and strong thermal stability. At the same time, the three nitrogen atoms and carbon atoms in the triazine ring are arranged alternately, forming a highly conjugated π-electron system. This structure can effectively absorb ultraviolet light, convert high-energy ultraviolet photons into low-energy vibrations or heat energy. Therefore, when the present invention is used under light, the triazine group can absorb or scatter ultraviolet energy, reduce the photolysis of pesticide molecules, extend its field persistence period. At the same time, in areas with strong light, the drug effect is more stable, avoiding the decline of the control effect caused by rapid decomposition, and expanding the application scope of the present invention.

[0065] In the description of this specification, the description with reference 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.

[0066] 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 to replace them. 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 triazoles, 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 ingredient is a combination of isoproflupyram and a triazole fungicide, and the mass ratio of isoproflupyram to the triazole fungicide is 20-80:10-30.

2. The fungicidal composition containing isopropyram and triazoles according to claim 1, characterized in that: The mass ratio of isopropyram to the triazole fungicide is 40-60:10-20.

3. The fungicidal composition containing isopropyram and triazoles according to claim 1, characterized in that: The mass ratio of isopropyram to the triazole fungicide is 50:

15.

4. The fungicidal composition containing isopropyram and triazoles according to claim 1, characterized in that: The triazole fungicide is one or more of tebuconazole, difenoconazole, propiconazole, fluopicolide, myclobutanil, metconazole, trichlorfonazole, flusilazole, prothioconazole, tetrafluconazole, penconazole, triadimefon, hexaconazole, flutriafol, cyproconazole and bifenthrin.

5. The fungicidal composition containing isopropyram and triazoles according to claim 1, characterized in that: The auxiliary materials include the following raw materials in parts by weight: 10-20 parts by weight of lignin carboxylate pesticide (CMBL) dispersant, 2-3 parts by weight of K12-B wetting agent, 0.1-0.3 parts by weight of C6 defoamer, and 0.5-5 parts by weight of disintegrant sodium chloride.

6. The fungicidal composition containing isopropyram and triazoles according to claim 1, characterized in that: The herbicidal composition is mixed with common auxiliary materials of 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 triazoles according to claim 1, characterized in that: The preparation method of the composition containing isopropyram and triazoles 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 triazole 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, the pressure spray dryer is heated to 130-150° C. and spray-dried to obtain a fungicide composition containing isopropyram and triazoles.

8. Use of the fungicidal composition containing isopropyram and triazoles according to any one of claims 1 to 7, characterized in that: The bactericidal composition is used for preventing and controlling crop diseases, including downy mildew (cucumber downy mildew), late blight, Phytophthora root rot (Pythium cucurbitum), powdery mildew (wheat powdery mildew), rust, leaf spot (tomato early blight), anthracnose, and imperfect fungi (Fusarium moniliforme, cotton damping-off).

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