Application of alkyl pyridinium salt in prevention and treatment of plant parasitic nematodes
By developing alkylpyridine salt compounds, the problems of nematode resistance and environmental pollution caused by existing nematodes are solved, and efficient killing of pine nematodes and southern root knot nematodes is achieved, and the potential for development as new nematodes is achieved.
Patent Information
- Application Number
- CN202510229424.3
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2025-02-28
- Publication Date
- 2025-06-03
AI Technical Summary
After long-term large-scale use of existing chemical nematodes, they cause nematodes to develop drug resistance and have adverse effects on crops and the environment, and lack efficient and economical nematodes.
An alkyl pyridine salt compound was developed, including dodecylpyridine chloride, dodecylpyridine bromide, tetradecylpyridine chloride, hexadecylpyridine chloride monohydrate, hexadecylpyridine chloride, and bromohexadecylpyridine were found to have excellent nematicidal activity against pine nematode and nanro-knot nematode.
These alkylpyridine salt compounds show good nematodetic activity, have low toxicity and high safety, and are expected to be developed as new nematodes to effectively prevent and control plant nematode diseases caused by pine nematodes and southern root knot nematodes.
Smart Images
Figure CN120078026A_ABST
Abstract
Description
Technical Field
[0001] The present invention belongs to the field of medicinal chemistry, and discloses a new use of alkylpyridinium salts in controlling plant parasitic nematodes, specifically relating to controlling plant nematode diseases caused by Bursaphelenchus xylophilus and Meloidogyne incognita. Background Art
[0002] Plant parasitic nematode diseases are the second largest category of diseases after fungal diseases in worldwide agricultural production, seriously threatening crop production and causing huge economic losses every year. Plant parasitic nematodes have a wide range of hosts and strong adaptability to various environments, so they are very difficult to control and prevent.
[0003] At present, chemical control is still the main measure for controlling plant parasitic nematodes. However, in agricultural production practice, the long-term and large-scale use of traditional chemical nematicides will lead to nematodes developing drug resistance and have adverse effects on crops and the environment. In this context, how to develop new nematicides with brand-new chemical structures and action mechanisms has become an urgent problem to be solved.
[0004] The most common cationic surfactants at present are quaternary ammonium compounds. As cationic quaternary ammonium salt organic compounds with broad-spectrum antibacterial properties, alkylpyridinium bromides and chlorides, their quaternary ammonium pyridine surfactants have been widely used in the pharmaceutical industry due to their bactericidal properties. The present invention further develops and explores the nematicidal activity of alkylpyridinium bromides and chlorides. In the activity screening of a series of alkylpyridinium bromides and chlorides carried out by the research group, it was found that pyridinium dodecyl bromide, pyridinium dodecyl chloride, pyridinium tetradecyl chloride, cetylpyridinium chloride monohydrate, cetylpyridinium chloride, and cetylpyridinium bromide all showed excellent nematicidal activity against two major plant parasitic nematodes. Activity screening shows that these compounds can control plant nematode diseases caused by Bursaphelenchus xylophilus and Meloidogyne incognita. Therefore, the present invention aims to illustrate the use of alkylpyridinium salts in combating plant parasitic nematodes, provide a new strategy for nematode control, and make up for the gap in the types of nematicides on the market. Summary of the Invention
[0005] The purpose of the present invention is to provide a new use of alkylpyridinium salts in combating plant parasitic nematodes in view of the current lack of efficient and economical nematicidal agents.
[0006] The structure of the alkylpyridinium salt compound is as Figure 1 shown.
[0007] The nematode species with anti-nematode activity described in this application include: Bursaphelenchus xylophilus and Meloidogyne incognita.
[0008] It has the following advantages:
[0009] 1) The present invention discovers that among the tested alkylpyridine chlorides, cetylpyridinium chloride monohydrate, cetylpyridinium chloride, dodecylpyridinium chloride, and tetradecylpyridinium chloride all have good nematocidal activity. The nematocidal activity of cetylpyridinium chloride monohydrate against Bursaphelenchus xylophilus is the best, and the LC 50 value at 24 h is 4.03 μg / mL. The nematocidal activity of dodecylpyridinium chloride against Meloidogyne incognita is the best, and the LC 50 value at 24 h is 2.58 μg / mL.
[0010] 2) The present invention discovers that among the tested alkylpyridine bromides, dodecylpyridinium bromide and cetylpyridinium bromide have good nematocidal activity. Among them, the nematocidal activities of dodecylpyridinium bromide against Bursaphelenchus xylophilus and Meloidogyne incognita are both the best, and the LC 50 values at 24 h are 3.90 μg / mL and 3.02 μg / mL respectively.
[0011] 3) The present invention discovers that such high-activity alkylpyridinium salt compounds have a simple structure, low toxicity, safe to use, and excellent nematocidal activity, and are expected to be developed into new nematocides. Description of the Drawings
[0012] Figure 1 It is a schematic diagram of the compound structures of Examples 1 and 2 of the present invention. Detailed Embodiments
[0013] To better understand the present invention, the above content of the present invention is further described in detail through the following specific examples. However, this should not be construed as a limitation of the present invention. The experimental methods described in the following examples are all conventional methods unless otherwise specified.
[0014] Example 1: Determination of the Toxicity of Alkylpyridinium Salt Compounds against Bursaphelenchus xylophilus
[0015] 1. Obtaining of Bursaphelenchus xylophilus
[0016] The pine wood nematodes used in this experiment were obtained by laboratory culture, and the medium used was potato agar glucose medium (abbreviated as PDA). PDA medium formula: 200 g of potato (peeled), 20 g of glucose, 15 g of agar, 1000 mL of deionized water. After autoclaving at 121 °C for 20 min, it was taken out and reserved. Botrytis cinerea was inoculated onto the PDA medium, and the pine wood nematodes on Botrytis cinerea were collected by the Baermann funnel method for use in the experiment.
[0017] 2. Sample preparation
[0018] The alkylpyridinium salt compounds used in this example were purchased from Shanghai Macklin Biochemical Co., Ltd. and were prepared by dissolving them in DMSO (dimethyl sulfoxide).
[0019] 3. Experimental method
[0020] The nematocidal activity of the compounds was determined by the immersion method. Treatment group liquid systems made of sterile water and test compounds or control drugs at different concentrations were added to 48-well plates, with the number of nematodes per well controlled at about 50. Equal-concentration DMSO (dimethyl sulfoxide) was used as a control. Each test group was set up with three replicates and cultured at 25 °C. After 24 h, observations were made under a stereomicroscope. Nematodes that could move freely or respond to shaking the 48-well plate by moving the head and tail of their bodies were identified as live nematodes. After calculating the corrected mortality rate corresponding to each concentration, the median lethal concentration (LC 50 ) was obtained using the statistical analysis software IBM statistics SPSS27.0.
[0021]
[0022] 4. Experimental results
[0023] The nematocidal activity of the alkylpyridinium salt compounds against pine wood nematodes is shown in Table 1.
[0024] Table 1 Nematocidal activity of alkylpyridinium salt compounds against pine wood nematodes and LC 50 value
[0025]
[0026] As can be seen from the results in Table 1, pyridinium chloride dodecyl, pyridinium bromide dodecyl, pyridinium chloride tetradecyl, cetylpyridinium chloride monohydrate, cetylpyridinium chloride, and cetylpyridinium bromide involved in the present invention have good nematocidal activity against pine wood nematodes.
[0027] Example 2: Determination of the nematocidal activity of alkylpyridinium salt compounds against second-stage larvae of Meloidogyne incognita
[0028] Take the cucumber roots infected by Meloidogyne incognita. After washing the soil, cut the root knots into pieces, prepare a 1% sodium hypochlorite solution and wash the root knots thoroughly for 1 minute. Wash the remaining sodium hypochlorite solution with sterile water. Use a 500-mesh sieve to collect the eggs washed down, place the eggs in a petri dish with sterile water, and incubate them in an incubator at 28°C for 4 days. Collect the second-stage juveniles of Meloidogyne incognita obtained by hatching as experimental worms.
[0029] 2. Sample preparation
[0030] Same as Example 1.
[0031] 3. Experimental method
[0032] Same as Example 1.
[0033] 4. Experimental results
[0034] The nematicidal activities of alkylpyridinium salts against the second-stage juveniles of Meloidogyne incognita are shown in Table 2.
[0035] Table 2 Nematicidal activities of alkylpyridinium salts against the second-stage juveniles of Meloidogyne incognita at different concentrations and LC 50 value
[0036]
[0037] As can be seen from the results in Table 2, pyridinium chloride dodecyl, pyridinium bromide dodecyl, pyridinium chloride tetradecyl, cetylpyridinium chloride monohydrate, cetylpyridinium chloride, and cetylpyridinium bromide involved in the present invention have good nematicidal activities against the second-stage juveniles of Meloidogyne incognita, and their nematicidal activities are better than those of the commercial pesticide fosthiazate.
[0038] In summary, the alkylpyridinium salts described in the present invention have good nematicidal activities and have the value of further research and development as new nematicides in agriculture.
Claims
1. The present invention relates to a new use of alkyl pyridinium salt compounds (which mainly include dodecyl pyridinium chloride, dodecyl pyridinium bromide, tetradecyl pyridinium chloride, cetyl pyridinium chloride monohydrate, cetyl pyridinium chloride, and cetyl pyridinium bromide) in preventing and controlling plant parasitic nematodes.
2. The use according to claim 1, wherein The molecular structure characteristics of dodecylpyridinium chloride are as follows.
3. The use according to claim 1, wherein The molecular structure characteristics of dodecylpyridinium bromide are as follows.
4. The use according to claim 1, wherein The molecular structure characteristics of tetradecylpyridinium chloride are as follows.
5. The use according to claim 1, wherein The molecular structure characteristics of cetylpyridinium chloride monohydrate are as follows.
6. The use according to claim 1, wherein The molecular structure characteristics of hexadecylpyridinium chloride are as follows.
7. The use according to claim 1, wherein The molecular structure characteristics of cetylpyridinium bromide are as follows.
8. Use of the dodecylpyridinium chloride according to claims 1 and 2 in controlling plant parasitic nematodes: pine wood nematode Bursaphelenchusxylophilus and southern root-knot nematode Meloidogyne incongnita.
9. Use of the dodecylpyridinium bromide according to claims 1 and 3 in controlling plant parasitic nematodes: pine wood nematode Bursaphelenchusxylophilus and southern root-knot nematode Meloidogyne incongnita.
10. Use of tetradecylpyridinium chloride according to claims 1 and 4 in controlling plant parasitic nematodes: pine wood nematode Bursaphelenchusxylophilus and southern root-knot nematode Meloidogyne incongnita.
11. Use of the cetylpyridinium chloride monohydrate according to claims 1 and 5 in controlling plant parasitic nematodes: pine wood nematode Bursaphelenchusxylophilus and southern root-knot nematode Meloidogyne incongnita.
12. Use of cetylpyridinium chloride according to claims 1 and 6 in controlling plant parasitic nematodes: pine wood nematode Bursaphelenchusxylophilus and southern root-knot nematode Meloidogyne incongnita.
13. Use of cetylpyridinium bromide according to claims 1 and 7 in controlling plant parasitic nematodes: pine wood nematode Bursaphelenchusxylophilus and southern root-knot nematode Meloidogyne incongnita.