Application of carbonyl compounds or carbonyl compound derivatives in the prevention and control of pathogens
By using carbonyl compounds or their derivatives to control soybean fungal diseases, the problem of complex infection caused by multiple pathogens in soybean fields has been solved, thereby improving soybean yield and quality.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- NORTHEAST AGRICULTURAL UNIVERSITY
- Filing Date
- 2023-08-04
- Publication Date
- 2026-06-30
AI Technical Summary
Soybean diseases are serious in the field due to complex infections, especially those caused by fungal pathogens such as Alternaria, Fusarium solani, and Fusarium trifidum, which lead to a decline in soybean yield and quality. Existing control methods are difficult to effectively control multiple pathogens.
Carbonyl compounds or their derivatives, such as trans-2-heptanal, 3-furan carbaldehyde, isobutyl butyrate, 1-acetylimidazole, and dimethyl phthalate, are used to control fungal diseases in soybeans by inhibiting the growth of pathogens and improving plant resistance.
It effectively inhibits soybean fungal diseases, improves plant resistance to pathogens, suppresses pathogenicity and mycelial growth, and enhances soybean yield and quality.
Smart Images
Figure CN117136952B_ABST
Abstract
Description
Technical Field
[0001] This invention belongs to the field of pesticide technology, specifically relating to the application of carbonyl compounds or derivatives of carbonyl compounds in the control of pathogens. Background Technology
[0002] my country is the origin of soybeans and has a long history of cultivation, with Northeast China being the main soybean producing area. During soybean cultivation, with the accumulation of continuous cropping years and increased land use, soybean diseases and pests have become increasingly severe, causing significant losses to the soybean industry. Soybean root rot, a common disease in the field, can generally cause a 30% yield reduction, and in severe cases, can lead to complete crop failure. Soybean gray spot disease affects the appearance of soybeans and reduces germination rate, lowering oil content by 2.9% and protein content by 1.2%. The complex infection of soybean diseases in the field is very serious, and the degree of damage is increasing, making prevention extremely difficult. Therefore, it is crucial to develop targeted control methods for soybean diseases to actively improve soybean yield and quality.
[0003] Soybean diseases are rarely caused by a single factor, and the diseases occurring at different stages of soybean growth vary. Among them, *Alternaria*, *Fusarium trifidum*, and *Fusarium solani* are all pathogens that can cause fungal diseases in soybeans. Therefore, finding substances that can inhibit the growth of multiple pathogens is imperative. Summary of the Invention
[0004] The purpose of this invention is to provide a novel pesticide ingredient for the prevention and control of diseases in soybeans.
[0005] This invention provides the application of a carbonyl compound or a derivative of a carbonyl compound in the prevention and control of pathogens, including at least one of the following applications:
[0006] (1) Prevention and control of pathogens;
[0007] (2) Improve plant resistance to pathogens;
[0008] (3) Inhibits the pathogenicity of pathogens;
[0009] (4) Inhibits the mycelial growth of pathogens;
[0010] Further specifying, the carbonyl compound is trans-2-heptanal, 3-furancarbaldehyde, isobutyl butyrate, 1-acetylimidazole, or dimethyl phthalate.
[0011] To further specify, the pathogen is a soybean fungus.
[0012] To further specify, the soybean fungi are Alternaria alternata, Fusarium solani, and Fusarium tricinctum.
[0013] This invention provides the application of a carbonyl compound or a derivative of a carbonyl compound in the prevention and control of pathogens, and its application in at least one of the following functional products.
[0014] (1) Prevention and control of pathogens;
[0015] (2) Improve plant resistance to pathogens;
[0016] (3) Inhibits the pathogenicity of pathogens;
[0017] (4) Inhibits the mycelial growth of pathogens;
[0018] Further specifying, the pathogens are Alternaria alternata, Fusarium solani, and Fusarium tricinctum.
[0019] The present invention provides a product containing a carbonyl compound or a derivative of a carbonyl compound for the application of preventing and controlling pathogens, wherein the active ingredient of the product is trans-2-heptanal or a derivative of trans-2-heptanal, and the product has at least one of the following functions: (1) preventing and controlling pathogens;
[0020] (2) Improve plant resistance to pathogens;
[0021] (3) Inhibits the pathogenicity of pathogens;
[0022] (4) Inhibits the mycelial growth of pathogens;
[0023] Further specifying, the pathogens are Alternaria alternata, Fusarium solani, and Fusarium tricinctum.
[0024] To further define the method, the specific steps are as follows: treating soybeans with a reagent containing a carbonyl compound or a derivative of a carbonyl compound used in the prevention and control of pathogens.
[0025] Further specifying, the disease is caused by the following pathogens: Alternaria alternata, Fusarium solani, and Fusarium tricinctum.
[0026] Beneficial effects: The aldehyde compounds provided by this invention can effectively inhibit the growth of various soybean fungal pathogens. The carbonyl compounds are trans-2-heptanal, 3-furanaldehyde, isobutyl butyrate, 1-acetylimidazole, and dimethyl phthalate. The fungal pathogens include Alternaria alternata, Fusarium solani, and Fusarium tricinctum. This compound has great potential in inhibiting soybean fungal diseases. Attached Figure Description
[0027] Figure 1 Inhibition of growth of Alternaria alternata, Fusarium solani, and Fusarium trifiliis by trans-2-heptanal, 3-furanaldehyde, isobutyl butyrate, 1-acetylimidazole, and dimethyl phthalate against commercial antimicrobial agents; Note: A: dimethyl phthalate; B: 3-furanaldehyde; C: trans-2-heptanal; D: isobutyl butyrate; E: 1-acetylimidazole; F: commercial antimicrobial agent.
[0028] Figure 2 The growth inhibition efficiency of trans-2-heptanal, 3-furanaldehyde, isobutyl butyrate, 1-acetylimidazole, dimethyl phthalate, and commercial antibacterial agents against Alternaria alternata, Fusarium solani, and Fusarium tricinctum. Detailed Implementation
[0029] The present invention will be further described in detail below with reference to specific embodiments. The embodiments given are only for illustrating the present invention and are not intended to limit the scope of the present invention.
[0030] Unless otherwise specified, the experimental methods described in the following examples are conventional methods.
[0031] Unless otherwise specified, all materials and reagents used in the following examples are commercially available.
[0032] The Alternaria alternata, Fusarium solani, and Fusarium tricinctum used in the following experiments were all isolated by Professor Li Yonggang's experimental team at Northeast Agricultural University and can also be commercially purchased.
[0033] The aldehyde compound trans-2-heptanal (CAS: 18829-55-5) was purchased from Macklin, catalog number: H838703. It is transparent.
[0034]
[0035] Liquid, chemical formula:
[0036] The heterocyclic compound 3-furanaldehyde (CAS: 498-60-2) was purchased from Macklin, catalog number: F810185. It is a transparent yellow to brown liquid with a slightly aromatic odor. Its structural formula is:
[0037]
[0038] Isobutyl butyrate (CAS: 539-90-2), an ester compound, was purchased from Macklin Company, catalog number: I858262. It is a colorless liquid with an apple and pineapple-like fruity aroma and sweetness. Chemical formula:
[0039]
[0040] The heterocyclic compound 1-acetylimidazole (CAS: 2466-76-4) was purchased from Macklin, catalog number: A800030. It is a colorless crystal, readily soluble in water and ethanol. Chemical formula:
[0041]
[0042] Dimethyl phthalate (CAS: 131-11-3), an ester compound, was purchased from Macklin, catalog number: D806666. It is a colorless, transparent, oily liquid with a slightly aromatic odor. Its chemical formula is:
[0043]
[0044] Example 1. Antibacterial experiment of trans-2-heptanal
[0045] 1. Preliminary preparation of the compound: A slow filter paper with a diameter of 6 mm was prepared using a punch. The compound trans-2-heptanal was then soaked in the filter paper until it was completely submerged.
[0046] 2. Prepare 1L of PDA medium. The specific steps are as follows: slice 300g of potatoes, add 1L of distilled water and boil. Filter out the potato residue with gauze. Add 30g of glucose (Sangon Biotech, Shanghai) and 26g of agar (Sigma, USA) to the remaining liquid and bring the volume to 1L. After high temperature and high pressure sterilization at 115℃ for 20min, store at 4℃ for later use.
[0047] 3. Inoculate the center of the PDA medium with 0.5 mm diameter inoculum blocks containing three species: *Alternaria alternata*, *Fusarium solani*, and *Fusarium trifilctum*. Then, evenly place three filter paper discs containing the compound 1 cm away from the medium. Simultaneously prepare a control medium without filter paper discs. Figure 1 The mycelium was incubated at 25°C for 48 hours in a dark environment. After the experiment, photographs were taken, and mycelial growth was analyzed using ImageJ software. The experiment was repeated three times. The mycelial growth of the control plate was considered 100%. The relative growth percentage of inoculated mycelium after compound treatment was calculated, and the inhibition rate was calculated by subtracting the mycelial growth rate from 100. The results are shown in [Figure number missing]. Figure 2 Table 1-3.
[0048] Example 2.3 - Antibacterial Experiment of Furan Formaldehyde
[0049] 1. Preliminary preparation of the compound: 6 mm diameter slow-speed filter paper was prepared using a punch, and the compound 3-furancarbaldehyde was soaked in the filter paper until it was completely submerged.
[0050] 2. Prepare 1L of PDA medium. The specific steps are as follows: slice 300g of potatoes, add 1L of distilled water and boil. Filter out the potato residue with gauze. Add 30g of glucose (Sangon Biotech, Shanghai) and 26g of agar (Sigma, USA) to the remaining liquid and bring the volume to 1L. After high temperature and high pressure sterilization at 115℃ for 20min, store at 4℃ for later use.
[0051] 3. Inoculate the center of the PDA medium with 0.5 mm diameter inoculum blocks containing three species: *Alternaria alternata*, *Fusarium solani*, and *Fusarium trifilctum*. Then, evenly place three filter paper discs containing the compound 1 cm away from the medium. Simultaneously prepare a control medium without filter paper discs. Figure 1 The mycelium was incubated at 25°C for 48 hours in a dark environment. After the experiment, photographs were taken, and mycelial growth was analyzed using ImageJ software. The experiment was repeated three times. The mycelial growth of the control plate was considered 100%. The relative growth percentage of inoculated mycelium after compound treatment was calculated, and the inhibition rate was calculated by subtracting the mycelial growth rate from 100. The results are shown in [Figure number missing]. Figure 2 Table 1-3.
[0052] Example 3. Antibacterial experiment of isobutyl butyrate
[0053] 1. Preliminary preparation of the compound: A slow filter paper with a diameter of 6 mm was prepared using a punch. Isobutyl butyrate was then soaked in the filter paper until it was completely submerged.
[0054] 2. Prepare 1L of PDA medium. The specific steps are as follows: slice 300g of potatoes, add 1L of distilled water and boil. Filter out the potato residue with gauze. Add 30g of glucose (Sangon Biotech, Shanghai) and 26g of agar (Sigma, USA) to the remaining liquid and bring the volume to 1L. After high temperature and high pressure sterilization at 115℃ for 20min, store at 4℃ for later use.
[0055] 3. Inoculate the center of the PDA medium with 0.5 mm diameter inoculum blocks containing three species: *Alternaria alternata*, *Fusarium solani*, and *Fusarium trifilctum*. Then, evenly place three filter paper discs containing the compound 1 cm away from the medium. Simultaneously prepare a control medium without filter paper discs. Figure 1 The mycelium was incubated at 25°C for 48 hours in a dark environment. After the experiment, photographs were taken, and mycelial growth was analyzed using ImageJ software. The experiment was repeated three times. The mycelial growth of the control plate was considered 100%. The relative growth percentage of inoculated mycelium after compound treatment was calculated, and the inhibition rate was calculated by subtracting the mycelial growth rate from 100. The results are shown in [Figure number missing]. Figure 2 Table 1-3.
[0056] Example 4.1 - Antibacterial test of acetylimidazole
[0057] 1. Preliminary preparation of the compound: A 6 mm diameter slow-speed filter paper was prepared using a punch. The filter paper was then soaked in a saturated solution (50 mg / mL) of the compound 1-acetylimidazole until it was completely submerged.
[0058] 2. Prepare 1L of PDA medium. The specific steps are as follows: slice 300g of potatoes, add 1L of distilled water and boil. Filter out the potato residue with gauze. Add 30g of glucose (Sangon Biotech, Shanghai) and 26g of agar (Sigma, USA) to the remaining liquid and bring the volume to 1L. After high temperature and high pressure sterilization at 115℃ for 20min, store at 4℃ for later use.
[0059] 3. Inoculate the center of the PDA medium with 0.5 mm diameter inoculum blocks containing three species: *Alternaria alternata*, *Fusarium solani*, and *Fusarium trifilctum*. Then, evenly place three filter paper discs containing the compound 1 cm away from the medium. Simultaneously prepare a control medium without filter paper discs. Figure 1 The mycelium was incubated at 25°C for 48 hours in a dark environment. After the experiment, photographs were taken, and mycelial growth was analyzed using ImageJ software. The experiment was repeated three times. The mycelial growth of the control plate was considered 100%. The relative growth percentage of inoculated mycelium after compound treatment was calculated, and the inhibition rate was calculated by subtracting the mycelial growth rate from 100. The results are shown in [Figure number missing]. Figure 2 Table 1-3.
[0060] Example 5. Antibacterial experiment of dimethyl phthalate
[0061] 4. Preliminary preparation of the compound: A slow filter paper with a diameter of 6 mm was prepared using a punch. The compound dimethyl phthalate was then soaked in the filter paper until it was completely submerged.
[0062] 5. Prepare 1L of PDA medium. Specific steps: Slice 300g of potatoes, add 1L of distilled water and boil. Filter out the potato residue with gauze. Add 30g of glucose (Sangon Biotech, Shanghai) and 26g of agar (Sigma, USA) to the remaining liquid and bring the volume to 1L. After high temperature and high pressure sterilization at 115℃ for 20min, store at 4℃ for later use.
[0063] In the center of the PDA medium, inoculate 0.5 mm diameter bacterial blocks containing three different fungi: *Alternaria alternata*, *Fusarium solani*, and *Fusarium trifiliis*. Then, evenly place three filter paper discs containing the compound 1 cm away from the medium. Simultaneously, prepare a control medium without filter paper discs. Figure 1 The mycelium was incubated at 25°C for 48 hours in a dark environment. After the experiment, photographs were taken, and mycelial growth was analyzed using ImageJ software. The experiment was repeated three times. The mycelial growth of the control plate was considered 100%. The relative growth percentage of inoculated mycelium after compound treatment was calculated, and the inhibition rate was calculated by subtracting the mycelial growth rate from 100. The results are shown in [Figure number missing]. Figure 2 Table 1-3.
[0064] Table 1. Inhibition efficiency of trans-2-heptanal, 3-furanaldehyde, isobutyl butyrate, 1-acetylimidazole, dimethyl phthalate, and commercial antibacterial agent (Runtian Nuoxin) against Alternaria alterniflora.
[0065]
[0066] Table 2. Inhibitory efficiency of trans-2-heptanal, 3-furanaldehyde, isobutyl butyrate, 1-acetylimidazole, dimethyl phthalate, and commercial antibacterial agents against Fusarium solani.
[0067]
[0068] Table 3. Inhibition efficiency of trans-2-heptanal, 3-furanaldehyde, isobutyl butyrate, 1-acetylimidazole, dimethyl phthalate, and commercial antibacterial agents against Fusarium trifidum.
[0069]
Claims
1. The use of trans-2-heptanal in at least one of the following, characterized in that, (1) Prevention and control of pathogens; (2) Improve the plant's resistance to pathogens; (3) Inhibits the pathogenicity of pathogens; (4) Inhibits the mycelial growth of pathogens; The pathogens are Alternaria alternata, Fusarium solani, and Fusarium tricinctum.
2. A method for improving the disease resistance of soybeans, characterized in that, The specific steps of the method are as follows: soybeans are treated with a reagent containing trans-2-heptanal; the disease is caused by the following pathogens: Alternaria alternata, Fusarium solani, and Fusarium tricinctum.