Chemical synthesis method, detection method and application of 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid

Abstract

The present invention discloses a chemical synthesis method, detection method, and application of 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid. The 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid prepared by this method was applied in field efficacy trials. The compound was found to promote wheat growth and increase yield in the field while being safe for wheat and other non-target organisms. The quality of starch, protein, and soluble sugar per unit mass of wheat was not reduced, ensuring wheat quality while increasing yield.

Description

Technical Field

[0001] The present invention belongs to the technical field of pesticides, and particularly relates to a chemical synthesis method, a detection method and an application of 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid. Background Art

[0002] The information disclosed in this background technology section is only intended to enhance understanding of the overall background of the invention and should not necessarily be regarded as an admission or any form of suggestion that the information constitutes the prior art already known to those skilled in the art.

[0003] Prior research on 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid has primarily focused on its anti-tumor, monoamide oxidase inhibition, and parasiticidal activities, with limited research on its plant-based properties. The patent, "Application and Preparation Method of Compound 1-Methyl-1,2,3,4-Tetrahydro-β-carboline-3-Carboxylic Acid" (Application Number: CN202310972464.8), discloses its potential to improve crop resistance to drought stress, enhance crop resistance to plant viruses, promote plant growth and yield, and enhance tomato resistance to root-knot nematodes. It also promotes plant absorption of nutrients and enhances their utilization by combining nutrients with other nutrients.

[0004] There is currently no in-depth research published on how to further improve the effectiveness of this substance in increasing agricultural production. Summary of the Invention

[0005] In order to address the deficiencies of the prior art, the present invention provides a chemical synthesis method, a detection method and an application of 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid.

[0006] In one aspect, the present invention provides a chemical synthesis method of 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid, comprising the following steps:

[0007] S1, adding L-tryptophan and acetaldehyde in a mass ratio of 1:0.5~1 into a reactor, and the reaction temperature is 30~50℃;

[0008] S2, add hydrochloric acid to the reaction solution, stir to mix, and let it stand for 24-36 hours;

[0009] S3, after the reaction of the above steps is completed, the pH is adjusted to 7-9 with NaOH to reduce the solubility of the product in water. Alkalinity can allow the product to precipitate and increase the yield;

[0010] S4, release the reaction solution and wash the product with water 2-3 times;

[0011] S5. Collect the product and dry it at 60-100° C. to obtain the compound 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid.

[0012] The present invention also provides a method for detecting 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid, including the identification of isomers, wherein the isomer structure is:

[0013] and

[0014] The liquid chromatography conditions used for the identification of the isomers provided by the present invention are:

[0015] Column: Eclipse Plus C18, 100×4.6 mm, 3.5 micron

[0016] Mobile phase: elution procedure is:

[0017]

[0018] Injection volume: 2.0 µL Column temperature: 30 °C

[0019] Detection wavelength: 220 nm

[0020] Flow rate: 1.0 mL / min

[0021] Run time: 15.0 min

[0022] Post-run time: 5.0 min

[0023] Mass spectrometry qualitative conditions (liquid phase)

[0024] Column: Eclipse Plus C18, 100×4.6 mm, 3.5 micron

[0025] Mobile phase: methanol water

[0026] 0.00 min1090

[0027] 8.00 min2080

[0028] Injection volume: 2.0 µL

[0029] Column temperature: 30 °C

[0030] Detection wavelength: 220 nm

[0031] Flow rate: 1.0 mL / min

[0032] Run time: 12.5 minutes

[0033] Post-run time: 5.0 min

[0034] Mass spectrometry quantification conditions (mass spectrometry part)

[0035] Ion source: API-ES, negative ion detection mode;

[0036] Dry gas N2: 10 L / min

[0037] Drying gas temperature: 350℃

[0038] Fragmentation voltage: 70 V

[0039] Atomizer pressure: 35 psig

[0040] Capillary transmission voltage: 3500 V

[0041] Mass scan range: 100-1000 amu.

[0042] The detection method of the present invention also includes a content determination method, and the chromatographic conditions are:

[0043] High performance liquid chromatography: equipped with fluorescence detector;

[0044] Acclaim 120 C18 column: 4.6 × 250 mm, 5 μm (or equivalent);

[0045] Mobile phase: Mobile phase A: water, mobile phase B: methanol;

[0046] Flow rate: 1.0 mL / min;

[0047] Column temperature: 35°C;

[0048] Detection wavelength: excitation wavelength: 260 nm; emission wavelength: 340 nm;

[0049] Injection volume: 5 μL;

[0050] Gradient elution conditions:

[0051]

[0052] Determination steps:

[0053] The assay method includes sample preparation:

[0054] Preparation of standard working solution: Prepare a 5 µg / mL 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid standard working solution.

[0055] Sample pretreatment:

[0056] Weigh 0.1 g of sample into a 100 mL volumetric flask, dilute to the mark with water, and mix thoroughly. Place 1 mL into a 1.5 mL centrifuge tube and centrifuge at 12,000 rpm for 10 min. Dilute an appropriate amount of the supernatant 250-fold with water, filter through a 0.22 µm aqueous filter, and then test.

[0057] Assay

[0058] Under the above operating conditions, after the instrument baseline is stable, continuously inject several needles of mixed standard working solution, calculate the relative response value of each needle, and when the relative response value change between two adjacent needles is less than 1.5%, measure the standard working solution and sample solution in sequence, and measure each sample twice in parallel.

[0059] In the content determination method,

[0060] Mass fraction of 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid in the sample X Calculate according to formula (1):

[0061] (1)

[0062] Where:

[0063] X ——mass fraction of the component to be tested in the sample, %;

[0064] A s——peak area of ​​the component to be measured in the standard working solution;

[0065] A i——peak area of ​​the component to be measured in the sample solution;

[0066] C s——the concentration of the component to be tested in the standard working solution, in µg / mL;

[0067] f ——dilution multiple;

[0068] v ——The fixed volume of the sample, in mL;

[0069] m ——Sample mass, in g.

[0070] The present invention also provides an application of 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid, which is used in increasing wheat yield.

[0071] Among them, the concentration of 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid is 0.0085~0.0115%.

[0072] Among them, the dosage of active ingredient is 0.02~0.033 mg / kg.

[0073] Furthermore, the application is that the application method is: the test agent 0.01% methylcarbolinic acid soluble solution, the recommended preparation dosage is 3000-5000 times liquid, that is, the dosage of the active ingredient is between 0.02-0.033 mg / kg, and the pesticide is sprayed once at the early tillering stage and the booting stage of wheat, with a water consumption of 40 L / mu.

[0074] Compared with the prior art, the present invention has the following beneficial effects:

[0075] 1. The present invention provides a chemical synthesis method for 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid, which has the advantages of a simple synthesis route, cheap and easily available raw materials, high yield, and a raw material conversion rate of 80% to 90%.

[0076] 2. The present invention applied the 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid prepared by the method to a field efficacy test, and found that the synthesized compound promoted wheat growth and increased yield in the field.

[0077] 3. Using 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid on wheat can effectively increase wheat plant height and effective ear number, effectively regulating and increasing wheat yield. It is also safe for wheat and other non-target organisms.

[0078] 4. When the 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid provided by the present invention is used for wheat, the quality of starch, protein and soluble sugar per unit mass of wheat is not reduced, thereby increasing the yield while ensuring the quality of wheat. BRIEF DESCRIPTION OF THE DRAWINGS

[0079] The accompanying drawings, which constitute a part of the present invention, are used to provide a further understanding of the present invention. The exemplary embodiments of the present invention and their descriptions are used to explain the present invention and do not constitute improper limitations on the present invention.

[0080] Figure 1 This is the liquid chromatogram of 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid in Example 2;

[0081] Figure 2 This is the NMR spectrum of 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (a) in Example 2;

[0082] Figure 3 This is the NMR spectrum of 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (b) in Example 2;

[0083] Figure 4 This is the liquid chromatogram of sample 1 in Example 3;

[0084] Figure 5 This is the liquid chromatogram of sample 2 in Example 3. DETAILED DESCRIPTION

[0085] It should be noted that the following detailed descriptions are exemplary and intended to provide further explanation of the present invention. Unless otherwise specified, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the art to which the present invention belongs.

[0086] Example 1: Synthesis of 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid compound

[0087] Add L-tryptophan and acetaldehyde into the reactor at a mass ratio of 1:0.5~1, and the reaction temperature is 30~50℃.

[0088] Add 0.05 mol / L hydrochloric acid to the reaction solution, stir to mix, and let it stand for 24 to 36 hours.

[0089] After the above steps are completed, the pH is adjusted to 7-9 with NaOH.

[0090] The reaction solution was discharged and the product was washed with water 2 to 3 times.

[0091] The product was collected and dried at 60-100°C to obtain the compound 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid, with the two isomers accounting for approximately 9:1.

[0092] In one embodiment, L-tryptophan and acetaldehyde are added to a reactor at a mass ratio of 1:0.5, and the reaction temperature is 40°C.

[0093] Add 0.05 mol / L hydrochloric acid to the reaction solution, stir to mix, and let it stand for 24 to 36 hours.

[0094] After the above steps are completed, the pH is adjusted to 8 with NaOH.

[0095] The reaction solution was discharged and the product was washed with water 2 to 3 times.

[0096] The product was collected and dried at 60-100°C to obtain the compound 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid. Liquid chromatography detection was used, and the peak area response value was used by area normalization method to calculate the ratio of the two isomers to be 85:15.

[0097] In another embodiment, L-tryptophan and acetaldehyde are added to the reactor in a mass ratio of 1:1, and the reaction temperature is 40°C.

[0098] Add 0.05 mol / L hydrochloric acid to the reaction solution, stir to mix, and let it stand for 24 to 36 hours.

[0099] After the above steps are completed, the pH is adjusted to 8 with NaOH.

[0100] The reaction solution was discharged and the product was washed with water 2 to 3 times.

[0101] The product was collected and dried at 60-100°C to obtain the compound 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid. Liquid chromatography detection was used, and the peak area response value was used by area normalization method to calculate the ratio of the two isomers to be 94:6.

[0102] Example 2: Identification of the Isomer Structures of 1-Methyl-1,2,3,4-Tetrahydro-β-Carboline-3-Carboxylic Acid Compounds

[0103] Instrument: Agilent HPLC 1100

[0104] Agilent HPLC 1200 / MSD 6120,

[0105] XS 205 analytical balance (accurate to 0.01 mg)

[0106] Reagents: Methanol (chromatographic grade), Water (ultrapure water)

[0107] Experimental conditions:

[0108] Liquid chromatography quantitative conditions:

[0109] Column: Eclipse Plus C18, 100×4.6 mm, 3.5 micron

[0110] Mobile phase: methanol water 0.00 min 10 90 8.00 min 20 80

[0111] Injection volume: 2.0 µL Column temperature: 30 °C

[0112] Detection wavelength: 220 nm

[0113] Flow rate: 1.0 mL / min

[0114] Run time: 15.0 min

[0115] Post-run time: 5.0 min

[0116] Mass spectrometry qualitative conditions (liquid phase)

[0117] Column: Eclipse Plus C18, 100×4.6 mm, 3.5 micron

[0118] Mobile phase: methanol water

[0119] 0.00 min1090

[0120] 8.00 min2080

[0121] Injection volume: 2.0 µL

[0122] Column temperature: 30 °C

[0123] Detection wavelength: 220 nm

[0124] Flow rate: 1.0 mL / min

[0125] Run time: 12.5 minutes

[0126] Post-run time: 5.0 min

[0127] Mass spectrometry quantification conditions (mass spectrometry part)

[0128] Ion source: API-ES, negative ion detection mode;

[0129] Dry gas (N2): 10 L / min

[0130] Drying gas temperature: 350℃

[0131] Fragmentation voltage: 70 V

[0132] Atomizer pressure: 35 psig

[0133] Capillary transmission voltage: 3500 V

[0134] Mass scan range: 100-1000 amu

[0135] Test method:

[0136] Weigh approximately 20 mg of 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid into a 10 ml volumetric flask, dissolve it in 70% methanol-water solution, dilute to volume, shake well, and filter through a 0.45 μm filter. After the instrument stabilizes, add this solution. Figures 1 to 3 shown.

[0137] According to the mass spectrometry results, the isomer structural formula of 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid compound is obtained as follows:

[0138] and

[0139] Example 3: Detection of 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid compounds

[0140] Method summary: The sample was dissolved in water and centrifuged and filtered. High performance liquid chromatography (HPLC) with a fluorescence detector was used with water and methanol as the mobile phase. The excitation and emission wavelengths were 260 nm and 340 nm, respectively. The methylcarbolinic acid in the sample was detected qualitatively by retention time and quantitatively by external standard method.

[0141] Reagents and solutions

[0142] Methanol: chromatographic grade;

[0143] Grade 1 water: meets the requirements of GB / T 6682 Grade 1 water;

[0144] 1-Methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid standard: purity ≥99.0%.

[0145] instrument

[0146] High performance liquid chromatography: equipped with fluorescence detector;

[0147] Acclaim 120 C18 column: 4.6 × 250 mm, 5 μm (or equivalent);

[0148] Analytical balance: precision 0.0001 g;

[0149] Centrifuge: Maximum speed not less than 12000 rpm / min;

[0150] Ultrasonic cleaning equipment;

[0151] Micropipette and matching tips;

[0152] Aqueous microporous membrane: 0.22 µm.

[0153] HPLC operating conditions

[0154] Mobile phase: Mobile phase A: water, mobile phase B: methanol;

[0155] Flow rate: 1.0 mL / min;

[0156] Column temperature: 35°C;

[0157] Detection wavelength: excitation wavelength: 260 nm; emission wavelength: 340 nm;

[0158] Injection volume: 5 μL;

[0159] Gradient elution conditions: see Table 1

[0160] Table 1 HPLC gradient elution conditions

[0161]

[0162] The above operating parameters are typical. According to the characteristics of different instruments, the given operating parameters can be appropriately adjusted to obtain the best results.

[0163] Measurement steps

[0164] Preparation of standard stock solutions

[0165] Accurately weigh 0.01 g (accurate to 0.0001 g) of 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid standard into a 10 mL volumetric flask, dissolve it in first-grade water and dilute to the mark. Mix well to obtain a 1 mg / mL 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid standard stock solution.

[0166] Preparation of standard intermediate solution

[0167] Accurately pipette 1 mL of the 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid standard stock solution into a 10 mL volumetric flask, dilute to the mark with water, and mix thoroughly to obtain a 100 µg / mL 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid standard intermediate solution.

[0168] Preparation of standard working solution

[0169] Accurately pipette 0.5 mL of the 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid standard intermediate solution into a 10 mL volumetric flask, dilute to the mark with water, and mix thoroughly to obtain a 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid standard working solution with a concentration of 5 µg / mL.

[0170] Sample pretreatment

[0171] Weigh 0.1 g of sample into a 100 mL volumetric flask, dilute to the mark with water, and mix thoroughly. Place 1 mL into a 1.5 mL centrifuge tube and centrifuge at 12,000 rpm for 10 min. Dilute an appropriate amount of the supernatant 250-fold with water, filter through a 0.22 µm aqueous filter, and then test.

[0172] Determination

[0173] Under the above operating conditions, after the instrument baseline is stable, inject several needles of mixed standard working solution continuously, calculate the relative response value of each needle, and when the relative response value of two adjacent needles changes by less than 1.5%, measure the standard working solution and sample solution in sequence, and measure each sample twice in parallel. The test results of the two samples are shown in Table 2 and Figure 4 、 Figure 5 shown.

[0174] calculate

[0175] Mass fraction of 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid in the sample X Calculate according to formula (1):

[0176] (1)

[0177] Where:

[0178] X ——mass fraction of the component to be tested in the sample, %;

[0179] A s ——In the standard working solution, the peak area of ​​the component to be measured is the sum of the peak areas of the two isomers;

[0180] A i ——In the sample solution, the peak area of ​​the component to be measured is the sum of the peak areas of the two isomers;

[0181] C s - the concentration of the component to be tested in the standard working solution, in micrograms per milliliter (µg / mL);

[0182] f ——dilution factor;

[0183] v ——The fixed volume of the sample, in milliliters (mL);

[0184] m ——mass of sample, in grams (g).

[0185] Table 2 Compound detection results

[0186]

[0187] Example 4: Effects of compound isomers on Arabidopsis growth

[0188] Soak an appropriate amount of Arabidopsis seeds in sterile water for 1 minute, sterilize with 5% sodium hypochlorite for 5 minutes, shake thoroughly, rinse three times with clean water, sterilize with 75% ethanol for 1 minute, rinse three to five times with sterile water, protect from light, and place in a 4°C refrigerator for vernalization for 2 days. Treatments are listed in Table 3.

[0189] Table 3 Experimental treatments

[0190]

[0191] Rosette diameter, number of bolts, bolt height, and number of pods were measured at the rosette leaf, bolting, and pod stages. After growth was complete, five plants were randomly selected from each treatment to calculate the total yield. The results are shown in Table 4.

[0192] Table 4 Effects of compound isomers on the growth and yield of Arabidopsis

[0193]

[0194] Compared with the control, when compound isomer a and compound isomer b were used at a concentration of 5 ng / mL, the leaf disk diameter, bolting height and pod quality of Arabidopsis thaliana were all improved to varying degrees, indicating that the compound isomers can promote plant growth and increase crop yield with significant effects.

[0195] Example 5: Field efficacy test of 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid soluble solution

[0196] 1-Methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid is mixed with a solvent to prepare a 0.01% soluble solution, referred to as 0.01% methylcarboline acid soluble solution.

[0197] Test site information

[0198] Experimental location: Xiagushan Village, Shangchuan Town, Yongdeng County, Lanzhou City, Gansu Province (E: 103.539921, N: 36.714567). Environmental conditions: The experimental field has a temperate continental climate with ample sunshine, mild weather, distinct seasons, moderate rainfall, flat terrain, and good irrigation conditions, making it suitable for the experiment. The previous crop was wheat. Soil type: light loam, pH 7.0, medium fertility, and complete irrigation facilities.

[0199] Application method

[0200] For spraying, the drug solution was prepared by the secondary dilution method. The blank control was first sprayed with an equal amount of clean water. The drug treatment area was sprayed uniformly one by one from low concentration to high concentration at a uniform speed, without repeated spraying or missing any spray. The sprayer was washed with clean water before spraying different drug treatments.

[0201] A total of 4 applications were made.

[0202] The first application: one application at the wheat seedling stage (treatment 5-treatment 6);

[0203] Second application: Apply once at the early stage of wheat tillering (treatments 1-4, 6);

[0204] The third application: one application at the wheat heading stage (treatments 1-4, 6);

[0205] The fourth application: apply the pesticide once during the wheat flowering period (treatment 5-treatment 6).

[0206] Community Design

[0207] The plots were arranged in random blocks, and the arrangement is shown in Table 5 .

[0208] Table 5 Cell arrangement

[0209]

[0210] Plot size and repetition

[0211] Cell area: 20 m 2 (5 m × 4 m), with 0.5 m protection rows set between cells.

[0212] Each treatment was replicated four times, for a total of 24 plots.

[0213] Experimental methods

[0214] Plant height: Sampling was conducted at 5 points per plot, with 10 plants randomly selected at each point. Number of effective ears: Sampling was conducted at 5 points per plot, with a sampling area of ​​1m 2 , investigate the number of effective ears in the sampling point. Number of grains per ear: sample 5 points in each plot, take 5 ears at each point, and investigate the number of grains per ear. Yield: harvest all the grains in each plot and dry them, measure the yield and calculate the yield per hectare (kg / hm2) 2 ), yield increase rate. Thousand-kernel weight: 1,000 kernels were randomly sampled from each plot and weighed, repeated five times. Quality measurement: 100 g of sun-dried wheat was selected from each plot and the soluble sugar (titration), starch (polarimetry), and protein (Kjeldahl method) contents were measured.

[0215] The experimental design of the test agents is shown in Table 6.

[0216] Pharmacological efficacy calculation method

[0217]

[0218] Table 6 Experimental design of test agents

[0219]

[0220] Results and Analysis

[0221] The test data were analyzed using the Duncan-New Multiple Range (DMRT) method of the DPS data processing system. The results are shown in Table 7.

[0222] Table 7 Experimental results on the effects of 0.01% methylcarbolinic acid soluble solution on wheat plant height, effective ear number, and number of grains per ear

[0223]

[0224] Note: In this table, uppercase and lowercase letters represent 1% and 5% significance levels, respectively; data are the average of 4 replicates for each treatment.

[0225] When the active ingredient dosage of 0.01% methylcarbolinic acid soluble solution was between 0.02 and 0.033 mg / kg, the wheat plant height was between 74.08 and 74.80 cm. The significance analysis showed that there were significant differences between the treatments and the blank control.

[0226] When the dosage of the tested agent, 0.01% methylcarbolinic acid soluble solution, was between 0.02 and 0.033 mg / kg, the number of effective wheat ears was between 406.85 and 414.60 ears / 1 m 2 A significance analysis revealed significant differences between test agent treatment 1 and blank control treatment 6, and extremely significant differences between test agent treatments 2 and 3 and blank control treatment 6. When the active ingredient dosage of the test agent, 0.01% methylcarbolinic acid soluble solution, was between 0.02 and 0.033 mg / kg, the number of filled grains per wheat ear ranged from 35.84 to 36.34 grains per ear. A significance analysis revealed no significant differences between the test agent treatments and the control agent or blank control.

[0227] Table 8 Experimental results on the effect of 0.01% methylcarbolinic acid soluble solution on wheat thousand-grain weight and yield

[0228]

[0229] Note: In this table, uppercase and lowercase letters represent 1% and 5% significance levels, respectively; data are the average of 4 replicates for each treatment.

[0230] As shown in Table 8, when the active ingredient dosage of 0.01% methylcarbolinic acid soluble solution ranged from 0.02 to 0.033 mg / kg, the thousand-grain weight ranged from 39.43 to 39.79 g. A significance analysis revealed no significant differences in thousand-grain weight between the treatments and the blank control.

[0231] When the dosage of 0.01% methylcarbolinic acid soluble solution is between 0.02 and 0.033 mg / kg, the wheat yield is between 11.15 and 11.60 kg / 20 m 2 The yield increase rate was between 8.79% and 13.17%. The significance analysis showed that there was a significant difference between the yield of wheat plots treated with each of the tested agents and the blank control.

[0232] Table 9 Test results of the effect of 0.01% methylcarbolinic acid soluble solution on wheat quality

[0233]

[0234] Note: The uppercase and lowercase letters in this table represent the 1% and 5% significance levels respectively; the data are the average of 4 replicates for each treatment

[0235] As shown in Table 9, there were no significant differences in the quality indicators among the test agents, control agents and blank control, indicating that the test agents and control agents had no significant effect on the quality of wheat.

[0236] Safety analysis: The test agent was 0.01% methylcarbolinic acid soluble solution, with a dosage of 2000-5000 times the liquid and an active ingredient dosage of 0.02-0.05 mg / kg. The agent was applied once at the early tillering stage and the heading stage of wheat. Visual inspection 3 days after each application showed that the wheat showed no signs of phytotoxicity such as leaf wilting, shrinking, and chlorosis. No effects on other non-target organisms (setaria, aphids) were observed, indicating that the test agent was safe to wheat and other non-target organisms.

[0237] Recommended application method: Taking into account various factors such as wheat yield and quality, the recommended dosage of the tested agent 0.01% methylcarbolinic acid soluble solution is 3000-5000 times, that is, the dosage of the active ingredient is between 0.02-0.033 mg / kg. Spray the pesticide once at the early tillering stage and the heading stage of wheat, with a water consumption of 40 L / mu (the amount after 0.01% methylcarbolinic acid is diluted 3000-5000 times with water). This can effectively increase the plant height and the number of effective ears of wheat, and has a good regulating and yield-increasing effect on wheat.

[0238] The foregoing description is merely a preferred embodiment of the present invention and is not intended to limit the present invention. Those skilled in the art will readily appreciate that various modifications and variations of the present invention are possible. Any modifications, equivalent substitutions, or improvements made within the spirit and principles of the present invention are intended to be within the scope of protection of the present invention.

Claims

1. Application of 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid, characterized in that: In the application of increasing wheat yield, the dosage of active ingredient is 0.02-0.033 mg / kg; the application method is: spray once at the early tillering stage and the heading stage of wheat.

2. The use according to claim 1, characterized in that The concentration of 1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid is 0.0085~0.0115%.

3. The use according to claim 1, characterized in that The application method is: water usage 40 L / mu.

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