Use of a berberine derivative in the prevention and treatment of plant parasitic nematodes
By using berberine derivative compounds 22, 23, and 25, the problems of chemical nematicide resistance and environmental hazards have been solved, achieving highly efficient and low-toxicity control of plant parasitic nematodes, demonstrating significant nematicidal activity and development potential.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- LANZHOU UNIV
- Filing Date
- 2025-01-16
- Publication Date
- 2026-06-12
AI Technical Summary
Existing chemical nematicides have problems with resistance when controlling plant parasitic nematodes and are harmful to the environment and human health. There is a need to find highly effective and low-toxicity bio-based nematicide lead compounds.
Berberine derivative compounds 22, 23, and 25 were used to control plant parasitic nematodes. Their biological activity was improved through structural modification, and they were developed into novel nematicides.
Berberine derivatives 22, 23, and 25 exhibit significant and broad-spectrum nematicidal activity, with LC50 values lower than existing agents, showing potential to become novel nematicides that are easy to synthesize and environmentally friendly.
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Abstract
Description
Technical Field
[0001] This invention belongs to the field of natural medicinal chemistry and discloses the use of a berberine derivative in the control of plant parasitic nematodes, specifically in the control of plant nematode diseases caused by pine wood nematode Bursaphelenchus xylophilus and southern root-knot nematode Meloidogyne incongnita. Background Technology
[0002] Plant parasitic nematode diseases have become the second largest category of agricultural diseases worldwide, after fungal diseases, causing approximately US$157 billion in economic losses annually. Among the most prevalent and severe plant parasitic nematode diseases in my country are root-knot nematode disease in cucumbers, pine wilt nematode disease in pine trees, and cyst nematode disease in soybeans. Plant parasitic nematodes can damage the vast majority of food and cash crops, and their strong environmental adaptability and rapid reproduction rate make plant nematode diseases extremely difficult to control.
[0003] Currently, chemical control remains the primary method for controlling plant parasitic nematodes. However, commercially available nematicides all have varying degrees of drawbacks, and long-term use of chemical nematicides can enhance nematode resistance, posing risks to the environment and human health. Against this backdrop, screening for highly effective and low-toxicity nematicidal lead compounds from biological sources such as plants or microorganisms is one of the main approaches to developing agents for controlling plant pathogenic nematodes.
[0004] Berberine, also known as berberine alkaloid, is a class of plant-derived natural alkaloids. Berberine and its derivatives are important lead compounds widely used in drug research for anti-inflammatory, antibacterial, and antitumor purposes. Derivatization and structural modification of the berberine nucleus can further expand its applications and significantly enhance its biological activity. This study tested the anti-plant parasitic nematode activity of a series of berberine derivatives. The results showed that compounds 22, 23, and 25 possessed broad-spectrum and excellent nematicidal activity, with some nematicidal activities superior to the positive control. Summary of the Invention
[0005] The purpose of this invention is to provide a new use of berberine compounds in the control of plant parasitic nematodes, for the prevention and treatment of plant diseases caused by plant parasitic nematodes.
[0006] The chemical structural formula involved in this invention is as follows:
[0007]
[0008]
[0009]
[0010] The nematicide provided by this invention has the following advantages:
[0011] 1) This invention found that berberine compounds exhibit good nematicidal activity against two plant parasitic nematodes, especially compounds 22, 23, and 25, which show significant and broad-spectrum nematicidal activity and can be further developed as lead compounds for nematicidal activity.
[0012] 2) These compounds are easy to synthesize and have a broad spectrum of anti-nematode activity, and are expected to be developed into new nematicides. Detailed Implementation
[0013] To better understand the present invention, the following specific embodiments further illustrate the above-described content of the present invention. However, this should not be construed as a limitation of the present invention. Unless otherwise specified, the experimental methods described in the following embodiments are conventional methods.
[0014] Example 1: Determination of the toxic activity of berberine compounds against pine wood nematode
[0015] 1. Obtaining pine wood nematodes
[0016] The pine wood nematodes used in this experiment were cultured in the laboratory using potato agar-dextrose medium (PDA). The PDA medium formula was: 200g peeled potato, 20g glucose, 15g agar, and 1000mL deionized water. The medium was autoclaved at 121℃ for 20 minutes and then set aside. *Botrytis cinerea* was inoculated onto the PDA medium, and the pine wood nematodes on the *Botrytis cinerea* were collected using the Bellman funnel method for experimental use.
[0017] 2. Sample preparation
[0018] Berberine hydrochloride (CAS: 633-65-8) used in this example was purchased from Tianjin Xiens Biochemical Technology Co., Ltd., while other compounds were synthesized in the laboratory.
[0019] 3. Experimental Methods
[0020] The nematicidal activity of the compounds was determined using the immersion method. Sterile water and treatment systems prepared with different concentrations of the test compound or control drug were added to 48-well plates. The nematode population per well was controlled to be approximately 50 nematodes. An equal concentration of DMSO (dimethyl sulfoxide) was used as a control. Each experimental group was replicated in triplicate. The nematodes were incubated at 25°C and observed under a stereomicroscope after 24 hours. Nematodes that could move freely or responded to shaking of the 48-well plate by moving their heads and tails were considered live nematodes. After calculating the corrected mortality rate for each concentration, the median lethal concentration (LC50) was determined using IBM Statistics SPSS 27.0 software.50 ).
[0021]
[0022] 4. Experimental Results
[0023] The toxic activity of berberine derivatives against pine wood nematode is shown in Table 1.
[0024] Table 1. Toxicity and LC50 of berberine derivatives against pine wood nematode at different concentrations 50 value
[0025]
[0026]
[0027] Note: "-" indicates that the corrected mortality rate for this concentration was not tested.
[0028] As shown in Table 1, the berberine derivatives involved in this invention exhibit good nematicidal activity against pine wood nematode, with compounds 22, 23, 25, and 26 showing the highest nematicidal activity (LC). 50 The values were all below 10 ppm.
[0029] Example 2: Assay of the toxic activity of berberine derivatives against second-instar larvae of the southern root-knot nematode
[0030] 1. Obtaining second-instar larvae of the southern root-knot nematode
[0031] Cucumber roots infected with southern root-knot nematodes were collected, the soil was washed away, the root knots were cut into pieces, and the root knots were thoroughly washed with a 1% sodium hypochlorite solution for 1 minute. The residual sodium hypochlorite solution was washed away with sterile water, and the washed-off nematode eggs were collected using a 500-mesh sieve. The nematode eggs were placed in a petri dish with sterile water and incubated in a constant temperature incubator at 28℃ for 4 days. The second instar larvae of southern root-knot nematodes obtained from the hatching were collected as experimental insects.
[0032] 2. Sample preparation
[0033] Same as Example 1.
[0034] 3. Experimental Methods
[0035] Same as Example 1.
[0036] 4. Experimental Results
[0037] Table 2 shows the toxic activity of berberine derivatives against second-instar larvae of the southern root-knot nematode.
[0038] Table 2. The toxic activity and LC50 of berberine derivatives against second-instar larvae of root-knot nematodes at different concentrations. 50 value
[0039]
[0040]
[0041]
[0042] Note: "-" indicates that the corrected mortality rate for this concentration was not tested.
[0043] As shown in Table 2, the compounds involved in this invention all exhibited certain toxic activity against second-instar larvae of the southern root-knot nematode. Among them, compounds 21, 22, 23, and 25 showed the following LC-15 activity. 50 The values were all less than 20 ppm, especially compounds 21 and 23, LC. 50 The values were all less than 10 ppm, and the nematicidal activity of the above four compounds against the second instar larvae of the southern root-knot nematode was superior to that of the positive control thiazophos (LC50). 50 The value was 18.396 ppm.
[0044] As shown in Tables 1 and 2, compounds 22, 23, and 25 involved in this invention exhibit good toxic activity against two major types of plant parasitic nematodes, and their toxic activity against second-instar larvae of the southern root-knot nematode is higher than that of the control drug thiazophos. Their LC50 values are [not specified in the original text]. 50 The values were slightly lower. Furthermore, compound 26 exhibited significant toxic activity against pine wood nematodes, with an LC50 value. 50 The concentration was 5.403 ppm. Compound 21 showed significant toxic activity against second-instar larvae of the southern root-knot nematode, with an LC50 concentration of 5.403 ppm. 50 It is 8.359 ppm.
[0045] In summary, the berberine derivatives described in this invention exhibit certain toxic activity against two major types of plant parasitic nematodes. In particular, compounds 22, 23, and 25 show excellent and broad-spectrum toxic activity, and can provide candidate agents for the integrated control of plant pathogenic nematodes.
Claims
1. The use of berberine derivatives in the control of pine wood nematode, wherein the berberine derivatives have the following chemical structure: 。 2. The use of berberine derivatives in the control of southern root-knot nematodes, wherein the berberine derivatives have the following chemical structure: 。