An L-tryptophanamide salt-based tobacco root-knot nematode inhibitor
By preparing L-tryptophan salt compounds, the problem of invasion of tobacco root knot nematodes is solved, and the effect of efficient killing and inhibiting nematodes is achieved. It is harmless to tobacco growth and has good biosafety.
Patent Information
- Application Number
- CN202510779084.1
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Filing Date
- 2025-06-12
- Publication Date
- 2025-08-26
- Estimated Expiration
- 2045-06-12
AI Technical Summary
The prior art is difficult to effectively inhibit the invasion of tobacco root knot nematodes, resulting in the hindered absorption of water and nutrients in the tobacco root system, weak growth of plants, and decreased yield and quality.
Tobacco root knot nematode inhibitors are prepared by specific synthesis steps using L-tryptophan salt compounds as active ingredients, including multi-step chemical reactions and mixing with chitosan to form compounds with good inhibitory and killing effects.
When directly acting on tobacco root knot nematodes, the mortality rate reached 78% in 24 hours and 86% in 48 hours. After root irrigation and application, the root knot index decreased by 77%, the SPAD value increased by 44%, and was harmless to plant growth, and the bee contact toxicity is low.
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Figure CN120283766B_ABST
Abstract
Description
Technical Field
[0001] The present invention relates to the technical field of pest repellents, in particular to an L-tryptophanamide salt-based tobacco root-knot nematode inhibitor. Background Art
[0002] Tobacco root-knot nematode disease is a major threat to tobacco production. Once the root-knot nematodes invade tobacco roots, they stimulate root cell proliferation, forming root knots of varying sizes. This severely impacts the tobacco root system's ability to absorb water and nutrients, leading to weak plant growth, yellowing leaves, reduced yield, and decreased quality. Therefore, the development of tobacco root-knot nematode inhibitors is of great significance to tobacco cultivation. Summary of the Invention
[0003] The present invention aims to provide an L-tryptophanamide salt-based tobacco root-knot nematode inhibitor, which has a good inhibitory effect on tobacco root-knot nematodes and can effectively block the parasitic channels of the root-knot nematodes and restore the normal growth of the plants.
[0004] To achieve the above object, the present invention provides the following technical solutions:
[0005] One of the technical solutions of the present invention:
[0006] An L-tryptophanamide salt-based tobacco root-knot nematode inhibitor, the structural formula of the active ingredient is:
[0007] ;
[0008] Wherein, R1 is selected from one of H and C1-C5 alkyl;
[0009] In the formula, R2 is selected from one of C1-C6 alkyl, C2-C4 acyl, C6-C9 phenyl, halogenated phenyl, C1-C3 alkoxyphenyl and nitrophenyl.
[0010] Preferably, R1 is selected from one of -H, -CH3 and -CH(CH3)2.
[0011] Preferably, R2 is selected from -CH3, 、-COCH3、 、 、 、 、 、 and One of them.
[0012] Furthermore, the synthesis method of the active ingredient comprises the following steps:
[0013] 1) L-tryptophan and R1CHO are placed in an organic solvent, and a catalytic amount of trifluoromethanesulfonic acid is added. Triethylsilane is then added dropwise to the mixed solution of L-tryptophan and R1CHO, reacted, and purified to obtain intermediate product A;
[0014] Among them, the structural formula of intermediate product A is ;
[0015] 2) placing the intermediate product A obtained in step 1) in thionyl chloride, and adding a catalytic amount of N,N-dimethylformamide, chlorinating, and purifying to obtain a chlorinated product. The chlorinated product is then placed in an organic solvent, and a solution of ammonia in tetrahydrofuran is added dropwise to the solution of the chlorinated product, reacting, and purifying to obtain an intermediate product B;
[0016] Among them, the structural formula of intermediate product B is ;
[0017] 3) placing the intermediate product B obtained in step 2) in an organic solvent, and adding a catalytic amount of potassium carbonate, then adding R2X dropwise to the solution of the intermediate product B, reacting, and purifying to obtain the intermediate product C;
[0018] Among them, the structural formula of intermediate product C is ;
[0019] 4) placing the intermediate product C obtained in step 3) in a nitrating agent for nitration to obtain a nitration product, and then mixing the nitration product, tin chloride and hydrochloric acid for reduction to obtain an intermediate product D;
[0020] Among them, the structural formula of intermediate product D is ;
[0021] 5) placing the intermediate product D obtained in step 4) in hydrochloric acid, and sequentially adding sodium nitrite and fluoroboric acid dropwise to the solution of the intermediate product D to react to obtain a diazotization product. Thereafter, a catalytic amount of silicon dioxide is added to the diazotization product and thermally decomposed to obtain the L-tryptophanamide salt-based tobacco root-knot nematode inhibitor active ingredient.
[0022] Furthermore, in step 1), the organic solvent is trifluoroacetic acid or dichloroethane.
[0023] Furthermore, in step 1), the molar ratio of L-tryptophan, R1CHO and triethylsilane is 1:(1.1-1.3):(1.1-1.3).
[0024] Furthermore, in step 1), the reaction is specifically carried out at 0° C. and monitored by thin layer chromatography until the L-tryptophan reaction is complete.
[0025] Furthermore, in step 2), the molar ratio of the intermediate product A to thionyl chloride is 1:(1.1-1.3).
[0026] Furthermore, in step 2), the chlorination is specifically carried out at room temperature and monitored by thin layer chromatography until the reaction of the intermediate product A is complete.
[0027] Furthermore, in step 2), the molar ratio of the chlorinated product to ammonia is 1:(1.1-1.3).
[0028] Furthermore, in step 2), the organic solvent is tetrahydrofuran or diethyl ether.
[0029] Furthermore, in step 2), the reaction is specifically carried out at 0°C and monitored by thin layer chromatography until the chlorinated product reacts completely.
[0030] Furthermore, in step 3), the organic solvent is N,N-dimethylformamide or dimethyl sulfoxide.
[0031] Furthermore, in step 3), the molar ratio of the intermediate product B to R2X is 1:(2.2-2.4).
[0032] Furthermore, in step 3), the reaction is specifically carried out at 0°C and monitored by thin layer chromatography until the intermediate product B is completely reacted.
[0033] Furthermore, in step 4), the nitrating agent is prepared by mixing concentrated sulfuric acid and concentrated nitric acid in a volume ratio of 2:1.
[0034] Furthermore, in step 4), the molar ratio of the intermediate product C to the nitrating agent is 1:(1.1-1.3).
[0035] Furthermore, in step 4), the nitration is specifically: nitration at room temperature for 1 to 1.5 hours.
[0036] Furthermore, in step 4), the molar ratio of the nitration product, tin chloride and hydrochloric acid is 1: (3-4): (6-8).
[0037] Furthermore, in step 4), the reduction is specifically carried out at room temperature and monitored by thin layer chromatography until the nitro point disappears.
[0038] Furthermore, in step 5), the molar ratio of the intermediate product D, sodium nitrite and fluoroboric acid is 1:(1.1-1.3):(1.1-1.3).
[0039] Furthermore, in step 5), the reaction is specifically carried out at 0° C. for 30 to 40 minutes.
[0040] Furthermore, in step 5), the temperature of the thermal decomposition is 60-90°C.
[0041] The synthesis steps of the active ingredient of the L-tryptophanamide salt tobacco root knot nematode inhibitor of the present invention are as follows:
[0042] .
[0043] The second technical solution of the present invention:
[0044] The preparation method of the above-mentioned L-tryptophanamide salt-based tobacco root-knot nematode inhibitor comprises the following steps:
[0045] The active ingredient, chitosan and water are mixed and stirred to obtain the L-tryptophanamide salt tobacco root-knot nematode inhibitor.
[0046] Furthermore, the mass ratio of the active ingredient, chitosan and water is (5-15): (20-30): (40-60).
[0047] Furthermore, the stirring is specifically: stirring at room temperature for 1 to 3 hours.
[0048] Compared with the prior art, the present invention has the following beneficial effects:
[0049] The L-tryptophanamide salt-based tobacco root-knot nematode inhibitor provided by the present invention, when directly acting on the second-instar larvae of tobacco root-knot nematodes, can achieve a 24-hour mortality rate of 78% and a 48-hour mortality rate of 86%. Compared with the commonly used insecticide avermectin, the L-tryptophanamide salt-based tobacco root-knot nematode inhibitor provided by the present invention has a better direct killing effect on tobacco root-knot nematodes;
[0050] After root irrigation and application of the L-tryptophanamide salt-based tobacco root-knot nematode inhibitor provided by the present invention, the root knot index can reach 1, the nematode reduction rate can reach 77%, and the SPAD value can reach 44. This indicates that the L-tryptanamide salt-based tobacco root-knot nematode inhibitor provided by the present invention has a good inhibitory effect on tobacco root-knot nematodes, can effectively block the parasitic pathways of root-knot nematodes, and restore normal plant growth.
[0051] When the L-tryptophanamide salt-based tobacco root-knot nematode inhibitor provided by the present invention is directly sprayed on the surface of K326 tobacco leaves, the leaves do not suffer from symptoms such as burns and deformities, and the inhibitor has low contact toxicity to bees, indicating that the L-tryptophanamide salt-based tobacco root-knot nematode inhibitor provided by the present invention has high biosafety. DETAILED DESCRIPTION
[0052] Various exemplary embodiments of the present invention are now described in detail. This detailed description should not be considered as a limitation of the present invention, but should be understood as a more detailed description of certain aspects, features, and embodiments of the present invention. It should be understood that the terms used in the present invention are only for describing specific embodiments and are not intended to limit the present invention.
[0053] In addition, for numerical ranges in the present invention, it is understood that each intervening value between the upper and lower limits of the range is also specifically disclosed. Each smaller range between any stated value or intervening value in a stated range and any other stated value or intervening value in the stated range is also included in the present invention. The upper and lower limits of these smaller ranges may independently be included or excluded in the range.
[0054] Unless otherwise indicated, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the art. Although only preferred methods and materials are described herein, any methods and materials similar or equivalent to those described herein may also be used in the practice or testing of the present invention. All documents mentioned in this specification are incorporated by reference to disclose and describe the methods and / or materials associated with the documents. In the event of any conflict with any incorporated document, the contents of this specification shall prevail.
[0055] It will be apparent to those skilled in the art that various modifications and variations may be made to the specific embodiments described herein without departing from the scope or spirit of the invention. Other embodiments will be apparent to those skilled in the art from the description of the invention. The description and examples are intended to be exemplary only.
[0056] The words “include,” “including,” “have,” “contain,” etc. used in this document are open-ended terms, meaning including but not limited to.
[0057] In the following examples, the synthesis method of the active ingredient of the tobacco root-knot nematode inhibitor based on L-tryptophanamide salts comprises the following steps:
[0058] 1) L-tryptophan and R1CHO are placed in trifluoroacetic acid or dichloroethane, and a catalytic amount of trifluoromethanesulfonic acid is added, with the molar ratio of L-tryptophan, R1CHO, and triethylsilane being 1:(1.1-1.3):(1.1-1.3). Triethylsilane is then added dropwise to the mixed solution of L-tryptophan and R1CHO at a drip rate of 30 d / min. The reaction is incubated at 0°C and monitored by thin-layer chromatography until the reaction of L-tryptophan is complete. The reaction is then purified by column chromatography to obtain intermediate A.
[0059] 2) placing the intermediate product A obtained in step 1) in thionyl chloride at a molar ratio of 1:(1.1-1.3) and adding a catalytic amount of N,N-dimethylformamide, and chlorinating at room temperature under thin layer chromatography monitoring until the reaction of the intermediate product A is complete, followed by column chromatography purification to obtain a chlorinated product. Subsequently, placing the chlorinated product in tetrahydrofuran or diethyl ether at a molar ratio of 1:(1.1-1.3) to ammonia, and adding a solution of ammonia in tetrahydrofuran dropwise to the solution of the chlorinated product at 0°C at a drip rate of 30 d / min, under thin layer chromatography monitoring until the reaction of the chlorinated product is complete, filtering, and purifying by column chromatography to obtain an intermediate product B;
[0060] 3) The intermediate product B obtained in step 2) is placed in N,N-dimethylformamide or dimethyl sulfoxide at a molar ratio of 1:(2.2-2.4), and a catalytic amount of potassium carbonate is added. R2X is then added dropwise to the solution of the intermediate product B at a rate of 30 d / min. The reaction is incubated at 0°C, monitored by thin-layer chromatography, until the reaction of the intermediate product B is complete. The reaction is then filtered and purified by column chromatography to obtain the intermediate product C.
[0061] 4) Concentrated sulfuric acid (98%) and concentrated nitric acid (68%) are mixed at a volume ratio of 2:1 to obtain a nitrating agent. The intermediate product C obtained in step 3) is then placed in the nitrating agent at a molar ratio of 1:(1.1-1.3) to the nitrating agent and nitrated at room temperature for 1-1.5 hours to obtain a nitrated product. The nitrated product, tin chloride, and hydrochloric acid are then mixed at a molar ratio of 1:(3-4):(6-8) to obtain a nitrated product. The mixture is reduced at room temperature and monitored by thin layer chromatography until the nitro point disappears. The mixture is separated and rotary evaporated to obtain an intermediate product D.
[0062] 5) The intermediate product D obtained in step 4) is placed in 10% hydrochloric acid at a molar ratio of 1:(1.1-1.3):(1.1-1.3). Sodium nitrite (15% aqueous solution) and fluoboric acid (40% aqueous solution) are sequentially added dropwise to the solution of the intermediate product D at 0°C at a drip rate of 30 d / min. The mixture is reacted for 30-40 minutes to obtain a diazotization product. A catalytic amount of silica is then added to the diazotization product, and the mixture is thermally decomposed at 60-90°C to obtain the L-tryptophanamide salt-based tobacco root-knot nematode inhibitor active ingredient.
[0063] Example 1
[0064] An active ingredient of L-tryptophanamide salt tobacco root-knot nematode inhibitor
[0065] This example uses the following synthetic route to synthesize the active ingredient:
[0066] ;
[0067] 1) L-tryptophan and HCHO were placed in trifluoroacetic acid or dichloroethane at a molar ratio of 1:1.2:1.2, and a catalytic amount of trifluoromethanesulfonic acid was added. Triethylsilane was then added dropwise to the mixed solution of L-tryptophan and HCHO at a rate of 30 d / min. The reaction was incubated at 0°C and monitored by thin-layer chromatography until the reaction of L-tryptophan was complete. The reaction was then purified by column chromatography to obtain intermediate A.
[0068] 2) placing the intermediate product A obtained in step 1) in thionyl chloride at a molar ratio of 1:1.2, and adding a catalytic amount of N,N-dimethylformamide. Chlorination is carried out at room temperature, monitored by thin layer chromatography, until the reaction of the intermediate product A is complete, and purified by column chromatography to obtain a chlorinated product. Subsequently, placing the chlorinated product in tetrahydrofuran or diethyl ether at a molar ratio of 1:1.2 to ammonia, and adding a solution of ammonia in tetrahydrofuran dropwise to the solution of the chlorinated product at 0°C at a drip rate of 30 d / min. Monitoring by thin layer chromatography, until the reaction of the chlorinated product is complete, filtering, and purifying by column chromatography to obtain an intermediate product B.
[0069] 3) The intermediate product B obtained in step 2) was placed in N,N-dimethylformamide or dimethyl sulfoxide at a molar ratio of intermediate product B to CH3Cl of 1:2.4, and a catalytic amount of potassium carbonate was added. Then, CH3Cl was added dropwise to the solution of intermediate product B at a rate of 30 d / min. The reaction was incubated at 0°C and monitored by thin-layer chromatography until the reaction of intermediate product B was complete. The reaction was then filtered and purified by column chromatography to obtain intermediate product C.
[0070] 4) Concentrated sulfuric acid (98%) and concentrated nitric acid (68%) were mixed at a volume ratio of 2:1 to obtain a nitrating agent. The intermediate product C obtained in step 3) was then placed in the nitrating agent at a molar ratio of 1:1.2 to the intermediate product C and the nitrating agent, and nitrated at room temperature for 1.2 hours to obtain a nitrated product. The nitrated product, tin chloride, and hydrochloric acid were then mixed at a molar ratio of 1:4:8 to obtain a nitrated product. The mixture was reduced at room temperature and monitored by thin layer chromatography until the nitro point disappeared. The mixture was separated and rotary evaporated to obtain an intermediate product D.
[0071] 5) The intermediate product D obtained in step 4) was placed in 10% hydrochloric acid at a molar ratio of 1:1.2:1.2 among the intermediate product D, sodium nitrite, and fluoroboric acid. Sodium nitrite (15% aqueous solution) and fluoroboric acid (40% aqueous solution) were sequentially added dropwise to the solution of the intermediate product D at 0°C at a drip rate of 30 d / min. The mixture was reacted for 35 minutes to obtain a diazotization product. A catalytic amount of silica was then added to the diazotization product, and the mixture was thermally decomposed at 70°C to obtain the L-tryptophanamide salt-based tobacco root-knot nematode inhibitor active ingredient.
[0072] Example 2
[0073] An active ingredient of L-tryptophanamide salt tobacco root-knot nematode inhibitor
[0074] Same as Example 1, except that HCHO in step 1) is replaced by CH3CHO, and CH3Cl in step 3) is replaced by ;
[0075] The specific synthetic route is as follows:
[0076] .
[0077] Example 3
[0078] An active ingredient of L-tryptophanamide salt tobacco root-knot nematode inhibitor
[0079] Same as Example 1, except that CH3Cl in step 3) is replaced by CH3COCl;
[0080] The specific synthetic route is as follows:
[0081] .
[0082] Example 4
[0083] An active ingredient of L-tryptophanamide salt tobacco root-knot nematode inhibitor
[0084] Same as Example 1, except that HCHO in step 1) is replaced by CH3CHO, and CH3Cl in step 3) is replaced by ;
[0085] The specific synthetic route is as follows:
[0086] .
[0087] Example 5
[0088] An active ingredient of L-tryptophanamide salt tobacco root-knot nematode inhibitor
[0089] Same as Example 1, except that HCHO in step 1) is replaced by (CH3)2CHCHO, and CH3Cl in step 3) is replaced by ;
[0090] The specific synthetic route is as follows:
[0091] .
[0092] Example 6
[0093] An active ingredient of L-tryptophanamide salt tobacco root-knot nematode inhibitor
[0094] Same as Example 1, except that HCHO in step 1) is replaced by CH3CHO, and CH3Cl in step 3) is replaced by ;
[0095] The specific synthetic route is as follows:
[0096] .
[0097] Example 7
[0098] An active ingredient of L-tryptophanamide salt tobacco root-knot nematode inhibitor
[0099] Same as Example 1, except that CH3Cl in step 3) is replaced by ;
[0100] The specific synthetic route is as follows:
[0101] .
[0102] Example 8
[0103] An active ingredient of L-tryptophanamide salt tobacco root-knot nematode inhibitor
[0104] Same as Example 1, except that HCHO in step 1) is replaced by (CH3)2CHCHO, and CH3Cl in step 3) is replaced by ;
[0105] The specific synthetic route is as follows:
[0106] .
[0107] Example 9
[0108] An active ingredient of L-tryptophanamide salt tobacco root-knot nematode inhibitor
[0109] Same as Example 1, except that HCHO in step 1) is replaced by (CH3)2CHCHO, and CH3Cl in step 3) is replaced by ;
[0110] The specific synthetic route is as follows:
[0111] .
[0112] Example 10
[0113] An active ingredient of L-tryptophanamide salt tobacco root-knot nematode inhibitor
[0114] Same as Example 1, except that CH3Cl in step 3) is replaced by ;
[0115] The specific synthetic route is as follows:
[0116] .
[0117] The L-tryptophanamide salt-based tobacco root-knot nematode inhibitor was prepared using the compounds synthesized in Examples 1 to 10 as the active ingredient of the L-tryptophanamide salt-based tobacco root-knot nematode inhibitor, which specifically includes the following steps:
[0118] The active ingredient, chitosan and water are mixed according to a mass ratio of 10:25:50, and stirred at room temperature for 1 to 3 hours to obtain the L-tryptophanamide salt tobacco root-knot nematode inhibitor.
[0119] Effect verification
[0120] 1. Laboratory in vitro activity test
[0121] Second-instar larvae (J2) of tobacco root-knot nematodes were isolated from infected tobacco root knots and suspended in sterile water;
[0122] 1 mL of the test reagent (L-tryptophanamide salt-based tobacco root-knot nematode inhibitor prepared using the compounds synthesized in Examples 1 to 10 as the active ingredient, at a concentration of 100 ppm) and 100 J2 larvae were added to each well of a multi-well plate. The plates were incubated in the dark at 25°C and examined under a microscope after 24 and 48 hours. The mortality rate was calculated (stiffness was considered death). The mortality calculation results are shown in Table 1.
[0123] Table 1 Mortality rate (%)
[0124]
[0125] As can be seen from the data in Table 1, when the L-tryptophanamide salt-based tobacco root-knot nematode inhibitor provided by the present invention directly acts on the second-instar larvae of tobacco root-knot nematodes, the 24-hour mortality rate of the second-instar larvae of tobacco root-knot nematodes can reach 78%, and the 48-hour mortality rate can reach 86%. Compared with the commonly used insecticide avermectin, the L-tryptophanamide salt-based tobacco root-knot nematode inhibitor provided by the present invention has a better direct killing effect on tobacco root-knot nematodes.
[0126] 2. Potted Plant Experiment
[0127] K326 tobacco plants were sown in pots (5 plants per pot). Two weeks after sowing, 1000 J2 larvae were inoculated in each pot. 24 hours after inoculation, the roots were irrigated with 50 mL / plant of a pesticide (L-tryptophanamide salt-based tobacco root-knot nematode inhibitor prepared using the compound synthesized in Examples 1 to 10 as the active ingredient, at a concentration of 100 ppm; avermectin, at a concentration of 50 ppm; and clean water). Three weeks after the application, the number of nematodes and plant growth indicators were tested. The results of the potted plant experiment are shown in Table 2.
[0128] Table 2 Potted plant test results
[0129]
[0130] As can be seen from the data in Table 2, after root irrigation and application of the L-tryptophanamide salt-based tobacco root-knot nematode inhibitor provided by the present invention, the root knot index can reach 1, the nematode reduction rate can reach 77%, and the SPAD value can reach 44. This shows that the L-tryptanamide salt-based tobacco root-knot nematode inhibitor provided by the present invention has a good inhibitory effect on tobacco root-knot nematodes, and can effectively block the parasitic pathways of root-knot nematodes and restore normal growth of plants.
[0131] 3. Biosafety Testing
[0132] The L-tryptophanamide salt-based tobacco root-knot nematode inhibitor prepared in Example 7 was subjected to a biosafety test. The test showed that when the L-tryptophanamide salt-based tobacco root-knot nematode inhibitor at a concentration of 1000 ppm was sprayed on the surface of K326 tobacco leaves, the leaves showed no burns or deformities.
[0133] After testing, it was found that after bees were exposed to a tobacco root-knot nematode inhibitor of L-tryptophanamide salt at a concentration of 1000ppm, the 48-hour mortality rate was only 26%, indicating low contact toxicity to bees.
[0134] Finally, it should be noted that the above embodiments are only used to illustrate the technical solutions of the present invention and not to limit it. Although the present invention has been described in detail with reference to the above embodiments, ordinary technicians in the field should understand that the specific implementation methods of the present invention can still be modified or replaced by equivalents. Any modification or equivalent replacement that does not depart from the spirit and scope of the present invention should be covered by the scope of protection of the claims of the present invention.
Claims
1. An L-tryptophanamide salt-based tobacco root-knot nematode inhibitor, characterized in that: The structural formula of the active ingredient of the L-tryptophanamide salt tobacco root-knot nematode inhibitor is: ； Wherein, R1 is selected from one of H and C1-C5 alkyl; In the formula, R2 is selected from one of C1-C6 alkyl, C2-C4 acyl, C6-C9 carbon chain substituted phenyl, halogenated phenyl, C1-C3 alkoxyphenyl and nitrophenyl.
2. The L-tryptophanamide salt-based tobacco root-knot nematode inhibitor according to claim 1, characterized in that: The synthesis method of the active ingredient comprises the following steps: 1) L-tryptophan and R1CHO are placed in an organic solvent, and a catalytic amount of trifluoromethanesulfonic acid is added. Triethylsilane is then added dropwise to the mixed solution of L-tryptophan and R1CHO, reacted, and purified to obtain intermediate product A; Among them, the structural formula of intermediate product A is ; 2) placing the intermediate product A obtained in step 1) in thionyl chloride, and adding a catalytic amount of N,N-dimethylformamide, chlorinating, and purifying to obtain a chlorinated product. The chlorinated product is then placed in an organic solvent, and a solution of ammonia in tetrahydrofuran is added dropwise to the solution of the chlorinated product, reacting, and purifying to obtain an intermediate product B; Among them, the structural formula of intermediate product B is ; 3) placing the intermediate product B obtained in step 2) in an organic solvent, and adding a catalytic amount of potassium carbonate, then adding R2X dropwise to the solution of the intermediate product B, reacting, and purifying to obtain the intermediate product C; Among them, the structural formula of intermediate product C is ; 4) placing the intermediate product C obtained in step 3) in a nitrating agent for nitration to obtain a nitration product, and then mixing the nitration product, tin chloride and hydrochloric acid for reduction to obtain an intermediate product D; Among them, the structural formula of intermediate product D is ; 5) placing the intermediate product D obtained in step 4) in hydrochloric acid, and sequentially adding sodium nitrite and fluoroboric acid dropwise to the solution of the intermediate product D to react to obtain a diazotization product. Thereafter, a catalytic amount of silicon dioxide is added to the diazotization product and thermally decomposed to obtain the L-tryptophanamide salt-based tobacco root-knot nematode inhibitor active ingredient.
3. The L-tryptophanamide salt-based tobacco root-knot nematode inhibitor according to claim 2, characterized in that: In step 1), the organic solvent is trifluoroacetic acid or dichloroethane; the molar ratio of L-tryptophan, R1CHO, and triethylsilane is 1:(1.1-1.3):(1.1-1.3); and the reaction is specifically carried out at 0°C and monitored by thin layer chromatography until the L-tryptophan reaction is complete.
4. The L-tryptophanamide salt-based tobacco root-knot nematode inhibitor according to claim 2, characterized in that: In step 2), the molar ratio of the intermediate product A to thionyl chloride is 1:(1.1-1.3); the chlorination is specifically carried out at room temperature and monitored by thin layer chromatography until the intermediate product A is completely reacted; the molar ratio of the chlorinated product to ammonia is 1:(1.1-1.3); the organic solvent is tetrahydrofuran or diethyl ether; and the reaction is specifically carried out at 0°C and monitored by thin layer chromatography until the chlorinated product is completely reacted.
5. The L-tryptophanamide salt-based tobacco root-knot nematode inhibitor according to claim 2, characterized in that: In step 3), the organic solvent is N,N-dimethylformamide or dimethyl sulfoxide; the molar ratio of the intermediate product B to R2X is 1:(2.2-2.4); and the reaction is specifically carried out at 0°C and monitored by thin layer chromatography until the reaction of the intermediate product B is complete.
6. The L-tryptophanamide salt-based tobacco root-knot nematode inhibitor according to claim 2, characterized in that: In step 4), the nitrating agent is prepared by mixing concentrated sulfuric acid and concentrated nitric acid in a volume ratio of 2:1; the molar ratio of the intermediate product C to the nitrating agent is 1:(1.1-1.3); the nitration is specifically carried out at room temperature for 1-1.5 hours; the molar ratio of the nitration product, tin chloride and hydrochloric acid is 1:(3-4):(6-8); the reduction is specifically carried out at room temperature and monitored by thin layer chromatography until the nitro point disappears.
7. The L-tryptophanamide salt-based tobacco root-knot nematode inhibitor according to claim 2, characterized in that: In step 5), the molar ratio of the intermediate product D, sodium nitrite and fluoroboric acid is 1:(1.1-1.3):(1.1-1.3); the reaction is specifically: reacting at 0°C for 30-40 minutes; in step 5), the temperature of the thermal decomposition is 60-90°C.
8. A method for preparing an L-tryptophanamide salt-based tobacco root-knot nematode inhibitor according to any one of claims 1 to 7, characterized in that: The following steps are involved: The active ingredient, chitosan and water are mixed and stirred to obtain the L-tryptophanamide salt tobacco root-knot nematode inhibitor.
9. The preparation method according to claim 8, characterized in that The mass ratio of the active ingredient, chitosan and water is (5-15): (20-30): (40-60).
10. The preparation method according to claim 8, characterized in that The stirring is specifically: stirring at room temperature for 1 to 3 hours.
Citation Information
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