Application of berberine derivative in prevention and treatment of plant parasitic nematodes

Abstract

The invention discloses application of a berberine derivative to prevention and treatment of plant parasitic nematode diseases. The compound has certain poisoning activity on plant pathogenic nematodes such as Bursaphelenchus xylophilus and Meloidogyne incongnita, particularly, the compound 22, the compound 23 and the compound 25 have broad-spectrum and excellent poisoning activity, and the nematicidal activity of part of the compound 22, the compound 23 and the compound 25 is superior to that of a positive control drug. The compound disclosed by the invention is easy to synthesize and excellent in activity, and is expected to be developed into a novel natural-source agricultural nematode-resistant medicament.

Description

Technical Field

[0001] The invention belongs to the field of natural drug chemistry, discloses a use of berberine derivatives in preventing and controlling plant parasitic nematodes, and specifically relates to preventing and controlling plant nematode diseases caused by pine wood nematodes Bursaphelenchusxylophilus and southern root-knot nematodes Meloidogyne incongnita. Background Art

[0002] Plant parasitic nematode diseases have become the second largest category of diseases in agricultural production around the world, second only to fungal diseases, causing economic losses of approximately US$157 billion each year. Among them, the most common and serious plant parasitic nematode diseases in my country include root knot nematode diseases of cucumbers, pine wood nematode diseases of pine trees, and cyst nematode diseases of soybeans. Plant parasitic nematodes can harm most food and cash crops, and have strong environmental adaptability and rapid reproduction rates. These characteristics make plant nematode diseases very difficult to prevent and control.

[0003] To date, chemical control is still the main means of controlling plant parasitic nematodes, but the nematicides widely used on the market have disadvantages to varying degrees, and long-term use of chemical nematicides will enhance the drug resistance of nematodes and cause harm to the environment and human health. In this context, screening high-efficiency, low-toxic nematicide lead compounds from biological sources such as plants or microorganisms is one of the main ways to develop agents for controlling plant pathogenic nematodes.

[0004] Berberine, also known as berberine, is a natural alkaloid derived from plants. Berberine and its derivatives are an important class of lead compounds, which are widely used in anti-inflammatory, antibacterial, anti-tumor and other drug research. Derivatization and structural modification of the berberine nucleus can further expand its use and significantly improve 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 have broad-spectrum and excellent nematicidal activity, and some of them have better nematicidal activity than the positive control drug. Summary of the invention

[0005] The purpose of the present invention is to provide a new use of berberine compounds in resisting plant parasitic nematodes, which is used for preventing and controlling plant diseases caused by plant parasitic nematodes.

[0006] The chemical structural formula involved in the present invention is as follows:

[0007]

[0008]

[0009]

[0010] The nematicide provided by the present invention has the following advantages:

[0011] 1) The present invention found that berberine compounds showed good nematicidal activity against two plant parasitic nematodes, especially compounds 22, 23, and 25 showed relatively significant and broad-spectrum nematicidal activity, and can be further developed as nematicidal lead compounds.

[0012] 2) This type of compound is easy to synthesize, has a broad spectrum of anti-nematode activity, and is expected to be developed into a new type of nematicide. DETAILED DESCRIPTION

[0013] In order to better understand the present invention, the above content of the present invention is further described in detail by the following specific examples. However, this should not be construed as limiting the present invention. The experimental methods described in the following examples are conventional methods unless otherwise specified.

[0014] Example 1: Determination of the toxicity of berberine compounds against pine wood nematodes

[0015] 1. Acquisition of pine wood nematodes

[0016] The pine wood nematodes used in this experiment were obtained by laboratory culture, and the culture medium used was potato agar glucose culture medium (PDA for short). PDA culture medium formula: 200g potatoes (peeled), 20g glucose, 15g agar, 1000mL deionized water, sterilized with high pressure steam at 121℃ for 20min, then taken out for use, Botrytis cinerea was inoculated on the PDA culture medium, and the pine wood nematodes on Botrytis cinerea were collected using the Baermann funnel method for experimental worms.

[0017] 2. Sample Preparation

[0018] Berberine hydrochloride (CAS: 633-65-8) used in this example was purchased from Tianjin Xiensi Biochemical Technology Co., Ltd., and other compounds were synthesized in the laboratory.

[0019] 3. Experimental Methods

[0020] The nematicidal activity of the compound was determined by the insect immersion method. Sterile water and different concentrations of the test compound or control drug were added to the 48-well plate. The number of worms in each well was controlled at about 50. The same concentration of DMSO (dimethyl sulfoxide) was used as a control. Three replicates were set for each test group. The worms were cultured at 25°C and observed under a stereo microscope after 24 hours. Nematodes that could move freely or respond to the shaking of the 48-well plate by moving their heads and tails were identified as live worms. After calculating the corrected dead worm rate corresponding to each concentration, the statistical analysis software IBM statistics SPSS27.0 was used to calculate the median lethal concentration (LC50).50 ).

[0021]

[0022] 4. Experimental Results

[0023] The toxicity of berberine derivatives to pine wood nematodes is shown in Table 1.

[0024] Table 1 Toxic activity and LC values ​​of berberine derivatives against pine wood nematodes at different concentrations 50 value

[0025]

[0026]

[0027] Note: “-” indicates that the corrected mortality rate of this concentration was not tested.

[0028] From the results in Table 1, it can be seen that the berberine derivatives of the present invention show good nematicidal activity against pine wood nematodes, among which compounds 22, 23, 25 and 26 have the highest nematicidal activity. 50 The values ​​were all below 10ppm.

[0029] Example 2: Determination of the toxicity of berberine derivatives against the second-instar larvae of southern root-knot nematodes

[0030] 1. Obtaining the Second-Instar Larvae of the Southern Root-Knot Nematode

[0031] Take the cucumber root system infected by southern root-knot nematodes, wash the soil, cut the root knots into pieces, prepare 1% sodium hypochlorite solution and thoroughly wash the root knots for 1 minute, use sterile water to wash the residual sodium hypochlorite solution, use a 500-mesh sieve to collect the washed eggs, place the eggs in a culture dish with sterile water, incubate them in a constant temperature box at 28°C for 4 days, and collect the hatched second-instar larvae of southern root-knot nematodes as experimental worms.

[0032] 2. Sample Preparation

[0033] Same as Example 1.

[0034] 3. Experimental Methods

[0035] Same as Example 1.

[0036] 4. Experimental Results

[0037] The toxicity of berberine derivatives against the second-instar larvae of southern root-knot nematode is shown in Table 2.

[0038] Table 2 Toxic activity and LC value 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 of this concentration was not tested.

[0043] From the results in Table 2, it can be seen that the compounds involved in the present invention all show certain toxicity against the second-instar larvae of southern root-knot nematodes. Among them, the LC values ​​of compounds 21, 22, 23, and 25 are 50 The values ​​were all less than 20 ppm, especially for 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 southern root-knot nematode was better than that of the positive control drug thiazolyl (LC 50 The value is 18.396ppm).

[0044] From the results in Table 1 and Table 2, it can be seen that the compounds 22, 23, and 25 of the present invention have good toxicity against two major types of plant parasitic nematodes, and their toxicity against the second-instar larvae of southern root-knot nematodes is higher than that of the control drug thiazolyl. 50 In addition, compound 26 has significant toxicity against pine wood nematodes, with LC 50 The toxicity of compound 21 to the second-instar larvae of southern root-knot nematode was significant, and the LC 50 It is 8.359ppm.

[0045] In summary, the berberine derivatives described in the present invention exhibit certain toxic activity against two major types of plant parasitic nematodes, especially compounds 22, 23, and 25, which exhibit excellent and broad-spectrum toxic activity, and can provide candidate agents for the comprehensive prevention and control of plant pathogenic nematodes.

Claims

1. The berberine derivatives described in the present invention have the following chemical structure:

2. Use of the berberine derivatives according to claim 1 in controlling pine wood nematodes.

3. Use of the berberine derivatives according to claim 1 in controlling southern root-knot nematodes.

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