Compound agent of botanical fungicide aromatic turmerone and azoxystrobin and application of compound agent

Through the combination of azoxystrobin and aromatic turmeric annyl turmeric annyl, a compound with a mass ratio of 0.27:1 to 0.54:1 was formed, which solved the problem of lack of compound ingredients for effective prevention and treatment of cucumber powdery mildew in the prior art, and achieved the goal of significantly improving the prevention and treatment effect and delaying drug resistance.

CN119867075AActive Publication Date: 2025-04-25SHANGHAI JIAOTONG UNIV
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Patent Information

Application Number
CN202510052476.8
Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
Filing Date
2025-01-14
Publication Date
2025-04-25
Estimated Expiration
2045-01-14

AI Technical Summary

Technical Problem

The prior art lacks aromatic turmericone complexes for the prevention and treatment of cucumber powdery mildew, making it difficult to effectively prevent and treat the disease.

Method used

By studying the complexity of azoxamine and aromatic turmericone, the ratio of the two to add the efficacy of the two to prevent and treat cucumber powdery mildew was formed, and a plant-derived fungicide complex was formed, including aromatic turmericone and aromatic turmericone, with a mass ratio of 0.27:1 to 0.54:1.

Benefits of technology

This compound has an additive effect in the prevention and treatment of cucumber powdery mildew, which significantly improves the prevention and treatment effect, delays the disease's resistance to a single agent, and reduces the use of azoxystrobin, reduces the cost and protects the ecological environment.

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Abstract

The invention provides a compound agent of botanical fungicide aromatic turmerone and azoxystrobin and application of the compound agent. The compound agent comprises an aromatic turmerone bactericide and azoxystrobin, and the mass ratio of the aromatic turmerone bactericide to the azoxystrobin is (0.27: 1)-(0.54: 1). The invention also provides an application of the compound agent in prevention and treatment of powdery mildew of cucumbers. Results of the invention prove that the aromatic turmerone bactericide and azoxystrobin in the compound agent have an additive effect on preventing and treating cucumber powdery mildew, so that a good compound effect can be realized, and the cucumber powdery mildew can be effectively prevented and treated.
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Description

Technical Field

[0001] The invention relates to the technical field of pesticides, and in particular to a compound of botanical fungicides turmeric flavonoids and azoxystrobin and an application thereof. Background Art

[0002] Currently, the combination of biopesticides and other pesticides is an important way to reduce the number and amount of pesticide applications to control plant diseases. Mixing biopesticides with other pesticides with different modes of action not only expands the scope of disease control, but also reduces the risk of pathogen resistance. Agricultural pathogens evolve pesticide resistance to withstand common pesticides, and pesticide resistance brings serious agricultural, environmental and socio-economic risks. Claire and other scholars observed in the process of powdery mildew control that long-term use of azole fungicides leads to increased pathogen resistance through three pathways: point mutation in the CYP51 amino acid sequence, overexpression of CYP51 enzymes, and overexpression of genes encoding efflux pump proteins. If Europe stops using azole fungicides, wheat production will drop by about 7% (9.8 million tons) in the short term, causing economic losses of up to 2.4 billion euros. Pesticide combination is an effective way to alleviate pesticide resistance. In addition, pesticide combination is also an important way to expand the scope of pesticide control. At present, most of the botanical pesticides in my country are registered and used in combination with broad-spectrum, high-efficiency biological pesticides or chemical pesticides to improve the rapid effect of biological pesticides, alleviate the resistance of chemical pesticides, and expand the scope of prevention and control. The current compound varieties include matrine with methomyl / cypermethrin / berberine, flavonoids with baicalin / zymosan, rotenone with pyrethrin / isothion / cypermethrin, etc.

[0003] The extensive use of chemical synthetic pesticides around the world has led to a series of problems such as food safety, excessive pesticide residues, target resistance, and ecological environment. The vigorous development of biopesticides has become an important development direction of the pesticide industry at home and abroad. As a biopesticide, botanical pesticides have the characteristics of low residue, environmental friendliness, and low resistance to targets, and have broad market space and application prospects. Cucumber powdery mildew is one of the main diseases of cucumber, usually caused by Sphaerotheca fuliginea and Erysiphe cichoracearum. It has the characteristics of frequent infection, short incubation period, and strong infectivity, which seriously affects its yield and quality. The Plant Health and Natural Products Laboratory of the College of Agriculture and Biology of Shanghai Jiao Tong University extracted and isolated ar-turmerone, the main active substance for the prevention and control of cucumber powdery mildew, from turmeric, and developed ar-turmerone mother drugs and preparations with significant control effects on cucumber powdery mildew. However, there is currently no ar-turmerone compound for the prevention and control of cucumber powdery mildew. Summary of the invention

[0004] In view of the defects in the prior art, the purpose of the present invention is to provide a compound of a botanical fungicide, turmeric flavonoids and azoxystrobin, and its application. Through the compounding study of azoxystrobin and turmeric flavonoids, the ratio of the two to add efficacy in preventing and controlling cucumber powdery mildew is determined to improve the control effect.

[0005] Azoxystrobin is a methoxyacrylate fungicide with a molecular weight of 403.388. It has the advantages of a wide control spectrum, high efficiency, and low toxicity. As a fungicide with a relatively broad spectrum, azoxystrobin has good control effects on fungal diseases such as cucumber downy mildew, turf brown spot, tobacco powdery mildew, watermelon anthracnose, tomato late blight, melon powdery mildew, turf wilt, corn leaf spot, lotus leaf spot, and mango anthracnose. Wang et al. found that the combination of azoxystrobin and fenpropimorph has a good control effect on tobacco brown spot; Li Wenjing et al. compounded azoxystrobin with ethoxylated and found that the combination of the two showed an additive effect on the control of four pathogenic fungi, Rhizoctonia solani, Fusarium oxysporum, Colletotrichum spp., and Neodiscus polytrichosporium.

[0006] Azoxystrobin has been used for a long time, and there have been many compound studies. It has formed compound agents with many pesticides and completed registration, such as propafenone·azoxystrobin, benzoyl·azoxystrobin, thiofuran·azoxystrobin, and azoxystrobin·chlorothalonil. The compounding of turmeric flavonoids and azoxystrobin has screened out new fungicide combinations, expanded the scope of prevention and control, and improved the prevention and control efficiency, providing a theoretical basis for the compounding of turmeric flavonoids and azoxystrobin to form new preparations in the future.

[0007] The chemical structure of turmeric flavonoids is Figure 1 The molecular weight is 216.319. The present invention uses 13% turmeric flavonoids mother drug to compound with azoxystrobin, osthole and other drugs, studies the interaction between turmeric flavonoids and different pesticides through indoor seedling stage in vivo bioassay, and explores the possibility of compounding turmeric flavonoids with other pesticides.

[0008] According to one aspect of the present invention, a compound of a botanical fungicide turmeric flavonoids and azoxystrobin is provided, wherein the compound comprises turmeric flavonoids fungicide and azoxystrobin, and the mass ratio of the turmeric flavonoids fungicide to the azoxystrobin is 0.27: 1 to 0.54: 1. Within this ratio range, the compound of turmeric flavonoids fungicide and azoxystrobin exhibits an additive effect.

[0009] Furthermore, the mass ratio of the aromatic turmeric flavonoid fungicide to the azoxystrobin is 0.36:1 to 0.54:1.

[0010] Furthermore, the mass ratio of the aromatic turmeric flavonoid fungicide to the azoxystrobin is 0.54: 1. The results in the embodiments of the present invention show that when the volume ratio of aromatic turmeric flavonoid to azoxystrobin is 1: 1, that is, when the weight ratio is 0.54: 1, the SR value is 1.286, and the compounding effect is the best.

[0011] Furthermore, the turmeric flavonoids fungicide is a turmeric flavonoids mother drug with an active ingredient content (mass percentage) of 13%.

[0012] Furthermore, the azoxystrobin is dissolved and diluted in DMSO. DMSO is a non-toxic solvent that can dissolve small polarity substances for living organisms, and other solvents are not recommended for use in living organisms.

[0013] Furthermore, the active ingredient concentration of the azoxystrobin is 13% (mass percentage).

[0014] Furthermore, since the aromatic turmeric flavonoid fungicide and the myclobutanil are not miscible, the compound further comprises a co-solvent to enable the two agents to be miscible.

[0015] Optionally, the co-solvent is 0.1% Tween-80.

[0016] According to another aspect of the present invention, there is provided a use of a compound of the botanical fungicide turmeric flavonoids and azoxystrobin in preventing and controlling powdery mildew of cucumber.

[0017] Furthermore, the application includes spraying the cucumber seedlings when two true leaves are fully expanded.

[0018] Furthermore, the application includes spraying the compound agent uniformly on cucumber seedlings so that the cucumber leaves are evenly covered with agent droplets.

[0019] In addition, it is worth noting that the results of the examples of the present invention show that when compounded with osthole, another biological fungicide for controlling cucumber powdery mildew, there is an antagonistic relationship between turmeric flavonoids and osthole. In agricultural production, care should be taken to avoid the use of the two pesticides together to ensure that the control effect is not lost.

[0020] Compared with the prior art, the present invention has at least one of the following beneficial effects:

[0021] The compound provided by the present invention comprises a turmeric flavonoid fungicide and azoxystrobin, and the mass ratio of the turmeric flavonoid fungicide to azoxystrobin is 0.27:1 to 0.54:1. The experimental results of the present invention prove that the turmeric flavonoid fungicide and azoxystrobin in the compound have an additive effect on the prevention and control of cucumber powdery mildew, thereby achieving a good compound effect, effectively preventing and controlling cucumber powdery mildew, thereby improving the safety and effectiveness of disease prevention and control. The compound can delay the resistance of the disease to a single agent or chemical pesticide, which is conducive to reducing the use of the chemical pesticide azoxystrobin, reducing costs, and protecting the ecological environment. BRIEF DESCRIPTION OF THE DRAWINGS

[0022] Other features, objects and advantages of the present invention will become more apparent from the detailed description of non-limiting embodiments made with reference to the following drawings:

[0023] Figure 1 It is the chemical structural formula of turmeric flavonoids. DETAILED DESCRIPTION

[0024] The present invention is described in detail below in conjunction with specific embodiments. The following embodiments will help those skilled in the art to further understand the present invention, but are not intended to limit the present invention in any form. It should be noted that, for those of ordinary skill in the art, several variations and improvements may be made without departing from the concept of the present invention. These all belong to the protection scope of the present invention.

[0025] Example

[0026] 1. Materials and instruments

[0027] 1.1 Test materials

[0028] Test reagents:

[0029] 13% aromatic turmeric flavonoids stock drug (i.e., active ingredient concentration of 130 mg / mL), provided by the Plant Health and Natural Products Laboratory, College of Agriculture and Biology, Shanghai Jiao Tong University;

[0030] Azoxystrobin (purity: 96.1%), provided by Wengkaier (Shanghai) Chemical Co., Ltd.;

[0031] Cucumber variety: Changfeng No. 2, a powdery mildew susceptible variety (Shanghai Baoshan District Vegetable Science and Technology Extension Station).

[0032] 1.2 Test equipment

[0033] Intelligent artificial climate chamber (Ningbo Jiangnan Instrument Factory, RXZ-500C-4);

[0034] Pipette (Dalong Xingchuang Experimental Instrument (Beijing) Co., Ltd., TopPette manual single-channel adjustable pipette, 1000-5000 μL);

[0035] Electronic balance (Mettler Toledo International Trading Shanghai Co., Ltd., ME104).

[0036] 2. Test methods

[0037] 2.1 Seedling cultivation

[0038] The cucumber seedlings were cultured in an incubator at 25°C and 70% humidity, and sprayed with bacterial suspension or pesticide when the two true leaves were fully expanded.

[0039] 2.2 Preparation of bacterial suspension and fungal inoculation

[0040] Use deionized water in a spray bottle to rinse cucumber leaves with powdery mildew spots to prepare a powdery mildew suspension; select cucumber seedlings with similar growth, place them in an inoculation box, and use a spray bottle to evenly spray the suspension on the cucumber leaves so that each leaf is evenly covered with droplets of the suspension. Cover the inoculation box and leave it for 24 hours, then open the lid and wait for the droplets on the leaves to dry naturally.

[0041] 2.3 Preparation of medicine

[0042] (1) Preparation of treatment agents

[0043] Azoxystrobin was dissolved in DMSO, and the concentration of the active ingredient was adjusted to 13%, i.e., 130 mg / mL. The azoxystrobin solution was compounded with 13% aromatic turmeric mother drug in volume ratios of 1:1, 1:2, and 2:3 (i.e., weight ratios of 0.54:1, 0.27:1, and 0.36:1), and 0.1% Tween-80 was added to aid dissolution.

[0044] (2) Preparation of control drug

[0045] Solvent control: 0.1% Tween-80 water was used as solvent control.

[0046] 2.4 Drug administration

[0047] Spray the cucumber seedlings evenly with each agent so that the cucumber leaves are evenly covered with agent droplets. Each treatment is repeated for 4 plants and the experiment is repeated 3 times. After the agent droplets are dried naturally, the cucumber plants are placed in an incubator for cultivation.

[0048] 2.5 Condition Investigation

[0049] The statistical method of cucumber disease index was carried out in accordance with "NY / T 1156.11-2008 Pesticide Indoor Bioassay Test Guidelines Fungicides Part 11: Test Pot Method for Control of Cucurbit Powdery Mildew". The disease was investigated 7 days after application and the disease status was recorded.

[0050] Disease classification standard:

[0051] Grade 0, no lesions;

[0052] Level 1, lesions occupy less than 5% of the leaf area;

[0053] Level 3: lesions occupy 5% to 15% of the leaf area;

[0054] Level 5: lesions occupy 15% to 35% of the leaf area;

[0055] Level 7: lesions occupy 35% to 55% of the leaf area;

[0056] Level 9: lesions occupy 55% to 75% of the leaf area;

[0057] Level 11: The lesions cover more than 75% of the leaf area

[0058] The disease index and control effect were calculated according to formula (1) and formula (2).

[0059]

[0060]

[0061] Among them, DI is the disease index; N i is the number of diseased leaves at each level; N is the total number of leaves investigated; i is the relative level value; DC is the control effect; DI CK DI is the disease index of the water control group; T It is the disease index after drug treatment.

[0062] Basic data statistics were processed using Excel 2016. EC50 values ​​and 95% confidence intervals were calculated using DPS software.

[0063] The Wadley method was used to evaluate the biological activity of the mixture of A (13% aromatic turmeric flavonoids parent drug) and B azoxystrobin (compound drug), and the SR value (synergistic ratio) was calculated according to the following formula (3) and formula (4).

[0064]

[0065]

[0066] Where: a and b are the ratios of A and B in the compound; EC (A)50 ,EC (B)50 The EC of A and B are 50 Measured value; EC 50(th) EC for compound preparation 50 Theoretical value; EC 50(ob) EC for compound preparation 50 Measured value. SR represents the interaction between A and B after mixing: SR < 0.5 represents antagonistic effect, 0.5 ≤ SR ≤ 1.5 represents additive effect, and SR > 1.5 represents synergistic or synergistic effect.

[0067] 3. Test results

[0068] The 13% aromatic turmeric flavonoids mother drug and azoxystrobin solution were compounded at a volume ratio of 1:1, 1:2, and 2:3, respectively, and the combined protective effect of the compound agent on cucumber powdery mildew was determined. The results of the determination using the seedling stage bioassay method are shown in Table 1.

[0069] Table 1 EC50 values ​​and toxicity regression equations of various ratios of azoxystrobin for the control of cucumber powdery mildew

[0070]

[0071] The results showed that different ratios of compound agents had different toxicity to cucumber powdery mildew. When V(aromatic turmeric flavonoids):V(pyraclostrobin)=1:1, that is, m(aromatic turmeric flavonoids):m(pyraclostrobin)=0.54:1, the SR value was the largest at 1.286, and the additive effect was the strongest.

[0072] Comparative Example

[0073] 1. Materials and instruments

[0074] 1.1 Test materials

[0075] Test reagents:

[0076] 13% turmeric flavonoids parent drug and 6.5% turmeric flavonoids emulsifiable concentrate were provided by the Plant Health and Natural Products Laboratory, College of Agriculture and Biology, Shanghai Jiao Tong University;

[0077] Osthole (purity 98%), provided by Shanghai Yiji Industrial Co., Ltd.;

[0078] Cucumber variety: Changfeng No. 2, a powdery mildew susceptible variety (Shanghai Baoshan District Vegetable Science and Technology Extension Station).

[0079] 1.2 Test equipment

[0080] Intelligent artificial climate chamber (Ningbo Jiangnan Instrument Factory, RXZ-500C-4);

[0081] Pipette (Dalong Xingchuang Experimental Instrument (Beijing) Co., Ltd., TopPette manual single-channel adjustable pipette, 1000-5000 μL);

[0082] Electronic balance (Mettler Toledo International Trading Shanghai Co., Ltd., ME104).

[0083] 2. Test methods

[0084] 2.1 Seedling cultivation

[0085] The cucumber seedlings were cultured in an incubator at 25°C and 70% humidity, and inoculated or sprayed when the two true leaves were fully expanded.

[0086] 2.2 Preparation of bacterial suspension and fungal inoculation

[0087] Use deionized water in a spray bottle to rinse the cucumber leaves with powdery mildew spots to prepare a powdery mildew suspension; select cucumber seedlings with similar growth, place them in an inoculation box, and use a spray bottle to evenly spray the suspension on the cucumber leaves so that each leaf is evenly covered with droplets of the suspension. Cover the inoculation box and leave it for 24 hours, then open the lid and wait for the droplets on the leaves to dry naturally.

[0088] 2.3 Preparation of medicine

[0089] (1) Preparation of treatment agents

[0090] Osthole was dissolved in DMSO, and the concentration of the active ingredient was adjusted to 13%, i.e., 130 mg / mL. The osthole solution was compounded with 13% aromatic turmeric mother drug in volume ratios of 1:1, 1:2, and 2:3 (i.e., mass ratios of 0.89:1, 0.44:1, and 0.59:1), and 0.1% Tween-80 was used as a solubilizing agent.

[0091] (2) Preparation of control drug

[0092] Positive control: 6.5% zingerbium flavonoids emulsifiable concentrate diluted 600 times was used as a positive control.

[0093] Solvent control: 0.1% Tween-80 water was used as solvent control.

[0094] 2.4 Drug administration

[0095] Spray the cucumber seedlings evenly with each agent so that the cucumber leaves are evenly covered with agent droplets. Each treatment is repeated for 4 plants and the experiment is repeated 3 times. After the agent droplets are dried naturally, the cucumber plants are placed in an incubator for cultivation.

[0096] 2.5 Condition Investigation

[0097] The statistical method of cucumber disease index was carried out in accordance with "NY / T 1156.11-2008 Pesticide Indoor Bioassay Test Guidelines Fungicides Part 11: Test Pot Method for Control of Cucurbit Powdery Mildew". The disease was investigated 7 days after application and the disease status was recorded.

[0098] Disease classification standard:

[0099] Grade 0, no lesions;

[0100] Level 1, lesions occupy less than 5% of the leaf area;

[0101] Level 3: lesions occupy 5% to 15% of the leaf area;

[0102] Level 5: lesions occupy 15% to 35% of the leaf area;

[0103] Level 7: lesions occupy 35% to 55% of the leaf area;

[0104] Level 9: lesions occupy 55% to 75% of the leaf area;

[0105] Level 11: The lesions cover more than 75% of the leaf area

[0106] The disease index and the control effect are calculated according to the above formula (1) and formula (2).

[0107] Basic data statistics were processed using Excel 2016. EC50 values ​​and 95% confidence intervals were calculated using DPS software.

[0108] The Wadley method was used to evaluate the biological activity of the mixture of A (13% aromatic turmeric flavonoids parent drug) and B osthole (compound drug), and the SR value (synergistic ratio) was calculated according to the above formula (3) and formula (4).

[0109] 3. Test results

[0110] The results of the disease investigation are shown in Table 2.

[0111] Table 2 EC50 values ​​and toxicity regression equations of various proportions of osthole for the prevention and treatment of cucumber powdery mildew

[0112]

[0113] According to the experimental results in Table 2, the EC50(ob) values ​​of osthole and turmeric at the ratios of 1:1, 1:2 and 2:3 were 0.1483 mg / mL, 0.1893 mg / mL and 0.1858 mg / mL, respectively. When the ratios were 1:1, 1:2 and 2:3, the SR values ​​were all SR<0.5, showing an antagonistic effect. The simultaneous use of turmeric and osthole should be avoided to ensure that the control effect is not lost.

[0114] The above describes the specific embodiments of the present invention. It should be understood that the present invention is not limited to the above specific embodiments, and those skilled in the art can make various modifications or variations within the scope of the claims, which does not affect the essence of the present invention. The above preferred features can be used in any combination without conflicting with each other.

Claims

1. A compound of a botanical fungicide turmeric flavonoids and azoxystrobin, characterized in that: The compound agent comprises turmeric flavonoid fungicide and azoxystrobin, and the mass ratio of the turmeric flavonoid fungicide to the azoxystrobin is 0.27:1 to 0.54:

1.

2. The compound of the botanical fungicide aromatic turmeric flavonoids and azoxystrobin according to claim 1, characterized in that: The mass ratio of the aromatic turmeric flavonoid fungicide to the azoxystrobin is 0.54:

1.

3. The compound of the botanical fungicide aromatic turmeric flavonoids and azoxystrobin according to claim 1, characterized in that: The aromatic turmeric flavonoids fungicide is an aromatic turmeric flavonoids mother drug with an effective component content of 13%.

4. The compound of the botanical fungicide aromatic turmeric flavonoids and azoxystrobin according to claim 1, characterized in that: The azoxystrobin is dissolved and diluted in DMSO.

5. The compound of the botanical fungicide aromatic turmeric flavonoids and azoxystrobin according to claim 4, characterized in that: The active ingredient concentration of the azoxystrobin is 13%.

6. The compound of the botanical fungicide aromatic turmeric flavonoids and azoxystrobin according to claim 1, characterized in that: The compounding agent also includes a co-solvent.

7. The compound of the botanical fungicide aromatic turmeric flavonoids and azoxystrobin according to claim 6, characterized in that: The cosolvent is 0.1% Tween-80.

8. Use of a compound of the botanical fungicide turmeric flavonoids and azoxystrobin according to any one of claims 1 to 7 in preventing and controlling powdery mildew of cucumber.

9. The use according to claim 8, characterized in that: The application includes spraying the cucumber seedlings when their two true leaves are fully expanded.

10. The use according to claim 8, characterized in that: The application comprises spraying the compound agent uniformly on cucumber seedlings so that the cucumber leaves are evenly covered with agent droplets.

Citation Information

Patent Citations

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