CN111766313B - Chloroindole hydrazide content analysis method - Google Patents
Chloroindole hydrazide content analysis method Download PDFInfo
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- CN111766313B CN111766313B CN202010500477.1A CN202010500477A CN111766313B CN 111766313 B CN111766313 B CN 111766313B CN 202010500477 A CN202010500477 A CN 202010500477A CN 111766313 B CN111766313 B CN 111766313B
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/04—Preparation or injection of sample to be analysed
- G01N30/06—Preparation
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/26—Conditioning of the fluid carrier; Flow patterns
- G01N30/28—Control of physical parameters of the fluid carrier
- G01N30/30—Control of physical parameters of the fluid carrier of temperature
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/26—Conditioning of the fluid carrier; Flow patterns
- G01N30/28—Control of physical parameters of the fluid carrier
- G01N30/32—Control of physical parameters of the fluid carrier of pressure or speed
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/26—Conditioning of the fluid carrier; Flow patterns
- G01N30/28—Control of physical parameters of the fluid carrier
- G01N30/34—Control of physical parameters of the fluid carrier of fluid composition, e.g. gradient
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/60—Construction of the column
- G01N30/6052—Construction of the column body
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/62—Detectors specially adapted therefor
- G01N30/74—Optical detectors
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
- G01N30/26—Conditioning of the fluid carrier; Flow patterns
- G01N30/28—Control of physical parameters of the fluid carrier
- G01N30/32—Control of physical parameters of the fluid carrier of pressure or speed
- G01N2030/324—Control of physical parameters of the fluid carrier of pressure or speed speed, flow rate
Abstract
The invention relates to the technical field of production of pesticide raw medicines, in particular to a chloroindoxyl hydrazide content analysis method, which adopts a high performance liquid chromatography for analysis and comprises the steps of (1) respectively dissolving a chloroindoxyl hydrazide standard substance and a sample to be detected by using a solvent to obtain a standard sample and a test sample; (2) adopting a high performance liquid chromatograph to perform sample injection analysis in sequence according to the sequence of a standard sample, a test sample and the standard sample; (3) calculating the average peak area of the chloroindole hydrazide in the standard sample and the sample, and calculating the average peak area according to the formula X1＝(A2×m1×P1)/(A1×m2) And calculating the content of the chloroindole hydrazide in the sample to be detected. The method has the advantages of strong specificity, good precision, high recovery rate, high reliability and good repeatability, and is especially suitable for quality control of pesticide raw drug products.
Description
Technical Field
The invention relates to the technical field of production of pesticide raw medicines, and particularly relates to a chloroindole hydrazide content analysis method.
Background
The chloroindole hydrazide is a compound containing an acylhydrazone structure, and has the chemical name of (1s,3s) -n' - (4-chlorophenylmethylene) -1-methyl-2, 3,4, 9-tetrahydropyrido [3,4-b ] indole-3-formylhydrazine. The chloroindole hydrazide has good anti-tumor and anti-virus activity, and the effect is expected in the field of preventing and treating plant virus diseases.
With the wider application of the chloroindole hydrazide, how to analyze the content of the chloroindole hydrazide becomes a problem to be solved urgently. At the present stage, a simple and efficient method for analyzing the content of the chloroindole hydrazide is still lacking.
Therefore, the method for analyzing the content of the chloroindoxyl has important effect and practical significance on ensuring the quality of the chloroindoxyl product.
Disclosure of Invention
Aiming at the problem that the prior art lacks a simple and efficient chloroindole hydrazide content analysis method, the invention provides the chloroindole hydrazide content analysis method which has strong specificity, good precision, high recovery rate, high reliability and good repeatability, and is particularly suitable for quality control of pesticide raw drug products.
A chloroindole hydrazide content analysis method adopts a high performance liquid chromatography for analysis, and specifically comprises the following steps:
(1) respectively dissolving a chloroindoxyl hydrazide standard substance and a sample to be detected by using a solvent to obtain a standard sample and a test sample;
(2) adopting a high performance liquid chromatograph to perform sample injection analysis in sequence according to the sequence of a standard sample, a test sample and the standard sample, wherein the chromatographic conditions are as follows:
a chromatographic column: a stainless steel column which takes octadecylsilane chemically bonded silica with the particle size of 4-5 mu m as a filler, the column length of 15-25cm and the theoretical plate number of 3000-5000;
mobile phase: a mixed system of acetonitrile and trifluoroacetic acid aqueous solution with volume fraction of 0.1%;
(3) calculating the average peak area of the chloroindole hydrazide in the standard sample and the sample, and calculating the average peak area according to the formula X1＝(A2×m1×P1)/(A1×m2) Calculating the content of the chloroindole hydrazide in the sample to be detected, wherein the formula is as follows:
X1-the content of chloroindoxyl hydrazide in the sample to be tested;
A1-average peak area of chloroindoxyl in the standard;
A2average of chloroindole hydrazides in the samplesPeak area;
m1-mass of chloroindolohydrazide in standard substance;
m2-the mass of chloroindoxyl hydrazide in the sample to be tested;
P1content of chloroindolhydrazide in standard substance.
Further, the solvent is at least one of N, N-dimethylformamide and methanol.
Furthermore, the chromatographic column takes octadecylsilane chemically bonded silica with the particle size of 5 mu m as a filler.
Further, the volume fraction of acetonitrile in the mobile phase is 30-50%. Most of the mobile phase is water phase, which reduces analysis time, improves the detection efficiency of the instrument and reduces the detection cost while ensuring the separation degree.
Further, the volume fraction of acetonitrile in the mobile phase was 45%.
Further, the volume of each injection was 5. mu.L.
Further, the flow rate of the mobile phase was 1 mL/min.
Further, the detection wavelength of the chloroindole hydrazide is 270 nm. 270nm is the most stable UV absorption wavelength of chloroindole hydrazide.
The beneficial effect of the invention is that,
the invention provides a method for analyzing the content of chloroindoxyl, which solves the problem that a method special for detecting the content of chloroindoxyl by high performance liquid chromatography is lacked in the prior art, a main peak and an adjacent impurity peak can be completely separated, the integral calculation result is accurate, the operability is good, the more accurate and timely real-time monitoring of the content of chloroindoxyl can be realized, and the method can be widely applied to the analysis and detection of the content of chloroindoxyl.
Detailed Description
In order to make those skilled in the art better understand the technical solutions in the present invention, the technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
In the implementation process, an LC-20AT high performance liquid chromatograph of Shimadzu corporation is adopted, and an LC-20AT solution pump and an SPD-M20A ultraviolet detector are arranged.
Example 1
85g of chloroindole hydrazide prepared in a small test 030 batch is subjected to content analysis, and the analysis method comprises the following steps:
(1) weighing 0.0502g of chloroindoxyl hydrazide standard substance, placing the weighed substance in a 100mL volumetric flask, adding 10mL of dimethylbenzamide, ultrasonically oscillating for dissolution, cooling to room temperature, and diluting to scale with methanol to obtain a standard sample;
weighing 0.0506g of chloroindoxyl hydrazide to be detected, placing the sample in a 100mL volumetric flask, adding 10mL of dimethylbenzamide, ultrasonically oscillating and dissolving, cooling to room temperature, and diluting to scale with methanol to obtain a sample;
(2) after the self-checking of the starting machine is passed, under the specified operation condition, after the instrument baseline is stable, a plurality of needle standard samples are continuously injected, the relative response value of each needle is calculated, when the relative response value of two adjacent needles changes by less than 1.5%, the samples are sequentially injected and analyzed according to the sequence of the standard samples, the test sample and the standard samples, the detection wavelength is 270nm, and the chromatographic condition is as follows:
the chromatographic column is filled with a stainless steel column of octadecylsilane chemically bonded silica of 5 μm, the length of the column is 15cm, the inner diameter is 4.6mm, the temperature of the column chamber is room temperature, and the number of theoretical plates is 3000;
taking a mixed system of acetonitrile and trifluoroacetic acid aqueous solution with volume fraction of 0.1% as a mobile phase, wherein the volume ratio of the acetonitrile to the trifluoroacetic acid aqueous solution is 45: 55, the flow rate is 1 mL/min;
the sample injection volume is 5 mu L;
(3) the results are shown in Table 1 below, substituting into formula X1＝(A2×m1×P1)/(A1×m2) And calculating to obtain the mass fraction of the chloroindoxyl in 030 batches of chloroindoxyl products (samples to be detected) to be 98.28 percent.
Table 1 example 1 test results
Example 2
320g of chloroindole hydrazide prepared in 150 lots of the small test sample is subjected to content analysis, and the analysis method comprises the following steps:
(1) weighing 0.0522g of chloroindole hydrazide standard substance, placing the standard substance in a 100mL volumetric flask, adding 20mL of methanol, ultrasonically oscillating for dissolution, cooling to room temperature, and diluting to scale with methanol to obtain a standard sample;
weighing 0.0518g of chloroindoxyl hydrazide to be detected, placing the sample in a 100mL volumetric flask, adding 20mL of methanol, ultrasonically oscillating for dissolution, cooling to room temperature, and diluting to a scale with methanol to obtain a sample;
(2) after the self-checking of the starting machine is passed, under the specified operation condition, after the instrument baseline is stable, a plurality of needle standard samples are continuously injected, the relative response value of each needle is calculated, when the relative response value of two adjacent needles changes by less than 1.5%, the samples are sequentially injected and analyzed according to the sequence of the standard samples, the test sample and the standard samples, the detection wavelength is 270nm, and the chromatographic condition is as follows:
the chromatographic column is filled with a stainless steel column of 4 mu m octadecylsilane chemically bonded silica, the length of the column is 20cm, the inner diameter is 4.6mm, the temperature of the column chamber is room temperature, and the number of theoretical plates is 5000;
taking a mixed system of acetonitrile and trifluoroacetic acid aqueous solution with volume fraction of 0.1% as a mobile phase, wherein the volume ratio of the acetonitrile to the trifluoroacetic acid aqueous solution is 45: 55, the flow rate is 1 mL/min;
the sample injection volume is 5 mu L;
(3) the results are shown in Table 2 below, substituting into formula X1＝(A2×m1×P1)/(A1×m2) And calculating to obtain 98.14% of the mass fraction of the chloroindoxyl in 150 batches of chloroindoxyl hydrazide products (samples to be tested).
Table 2 example 2 test results
Verification example 1
The method is repeatedly verified, and the verification method comprises the following steps:
(1) weighing 0.0526g of chloroindole hydrazide standard substance, placing the standard substance in a 100mL volumetric flask, adding 10mL of dimethylformamide, ultrasonically oscillating for dissolution, cooling to room temperature, and diluting to scale with methanol to obtain a standard sample;
weighing 6 parts of 0.05g (with the accurate value of 0.0002g) chloroindoxyl hydrazide sample to be detected, respectively placing the weighed 6 parts in a 100mL volumetric flask, adding 10mL of dimethylformamide, ultrasonically oscillating for dissolution, cooling to room temperature, and diluting to a scale with methanol to obtain 6 groups of parallel samples;
(2) after the self-checking of the starting machine is passed, under the specified operation condition, after the baseline of the instrument is stabilized, a plurality of needle standard samples are continuously injected, the relative response value of each needle is calculated, when the relative response value of two adjacent needles is changed to be less than 1.5 percent, the samples are sequentially injected and analyzed according to the sequence of the standard samples, the test sample and the standard samples, the detection wavelength is 270nm, and the chromatographic condition is the same as that of the embodiment 1;
(3) according to formula X1＝(A2×m1×P1)/(A1×m2) And calculating the content of the chloroindoxyl hydrazide in 6 groups of samples to be detected, wherein the result is shown in the following table 3, which indicates that the method has good repeatability.
Table 3 verification example 1 test results
Verification example 2
The method of the invention is verified in a linear relationship, and the verification method comprises the following steps:
(1) weighing the chloroindoxyl hydrazide standard substance, placing the chloroindoxyl hydrazide standard substance in a 100mL volumetric flask, adding 10mL of dimethylformamide, ultrasonically shaking for dissolution, cooling to room temperature, and then diluting to a scale with methanol to obtain a group of chloroindoxyl hydrazide samples with the concentrations of 153 mu g/mL, 216 mu g/mL, 310 mu g/mL, 424 mu g/mL, 511 mu g/mL, 604 mu g/mL, 696 mu g/mL and 817 mu g/mL;
(2) after the self-checking of the starting machine is passed, under the specified operation condition and after the instrument baseline is stable, the measurement is carried out under the wavelength of 270nm, and the chromatographic condition is the same as that of the embodiment 1;
(3) linear regression of the peak area to the sample concentration gave the regression equation y 173888x +5759.6, R20.9999, the chloroindole hydrazide has good linear relation in the range of 150-800 ug/ml.
Verification example 3
The method disclosed by the invention is subjected to precision verification, and the verification method comprises the following steps:
(1) different personnel accurately weigh 0.05g (accurate to 0.0002g) of chloroindole hydrazide 6 parts in different laboratories, respectively put in 100mL volumetric flasks, add 10mL of dimethylformamide, ultrasonically oscillate and dissolve, cool to room temperature, dilute to the scale with methanol, obtain a set of samples for intermediate precision tests;
(2) after the self-checking of the starting machine is passed, under the specified operation condition and after the instrument baseline is stable, the measurement is carried out under the wavelength of 270nm, and the chromatographic condition is the same as that of the embodiment 1;
(3) according to formula X1＝(A2×m1×P1)/(A1×m2) And calculating the content of the chloroindoxyl hydrazide in 6 groups of samples to be detected, wherein the result is shown in the following table 4, which indicates that the method has good intermediate precision.
Table 4 verification example 3 test results
Verification example 4
The method disclosed by the invention is subjected to stability verification, and the verification method comprises the following steps:
(1) weighing 6 parts of a sample of 0.05g (accurate to 0.0002g) of chloroindole hydrazide, respectively placing the sample in a 100mL volumetric flask, adding 10mL of dimethylformamide, ultrasonically oscillating and dissolving, cooling to room temperature, and diluting to a scale with methanol to obtain a group of samples for time stability tests;
(2) after the self-checking of the starting machine is passed, under the specified operation condition and after the instrument baseline is stable, the sample introduction is respectively carried out for 0, 1, 2, 4, 8 and 24 hours, the measurement is carried out under the wavelength of 270nm, and the chromatographic condition is the same as that of the embodiment 1;
(3) the results are shown in Table 5 below, which shows that the method of the present invention is excellent in stability with time.
Table 5 verification example 4 test results
| Time | 0h | 1h | 2h | 4h | 8h | 24h | RSD％ |
| Peak area | 9111019 | 9109573 | 9113824 | 9121574 | 9128516 | 9133255 | 0.11 |
Verification example 5
The method of the invention is subjected to the benchmarking recovery rate verification, and the verification method comprises the following steps:
(1) weighing 3 parts of chloroindole hydrazide samples of 0.02g, 0.03g and 0.04g, respectively placing the samples in a volumetric flask of 100mL, adding 10mL of methanol for ultrasonic oscillation and dissolution, accurately adding standard samples of 3.0mL, 2.0mL and 1.0mL respectively with the concentration of 10.007mg/mL, and diluting the samples to a scale by using methanol to obtain a group of samples for the standard-added recovery test;
(2) after the self-checking of the starting machine is passed, under the specified operation condition and after the instrument baseline is stable, the measurement is carried out under the wavelength of 270nm, and the chromatographic condition is the same as that of the embodiment 1;
(3) the results are shown in Table 6 below, which illustrates the good recovery of the spiked samples according to the method of the present invention.
Table 6 verification example 5 test results
Although the present invention has been described in detail by way of preferred embodiments, the present invention is not limited thereto. Various equivalent modifications or substitutions can be made on the embodiments of the present invention by those skilled in the art without departing from the spirit and scope of the present invention, and these modifications or substitutions are within the scope of the present invention/any person skilled in the art can easily conceive of the changes or substitutions within the technical scope of the present invention. Therefore, the protection scope of the present invention shall be subject to the protection scope of the claims.
Claims (6)
1. The method for analyzing the content of the chloroindole hydrazide is characterized by adopting a high performance liquid chromatography for analysis, and specifically comprises the following steps:
(1) respectively dissolving a chloroindoxyl hydrazide standard substance and a sample to be detected by using a solvent to obtain a standard sample and a test sample;
(2) adopting a high performance liquid chromatograph to perform sample injection analysis in sequence according to the sequence of a standard sample, a test sample and the standard sample, wherein the chromatographic conditions are as follows:
a chromatographic column: a stainless steel column which takes octadecylsilane chemically bonded silica with the particle size of 4-5 mu m as a filler, the column length is 15-25cm, and the theoretical plate number is 3000-;
mobile phase: a mixed system of acetonitrile and trifluoroacetic acid aqueous solution with the volume fraction of 0.1 percent, wherein the volume fraction of the acetonitrile is 45 percent;
(3) calculating the average peak area of the chloroindole hydrazide in the standard sample and the sample, and calculating the average peak area according to the formula X1＝(A2×m1×P1)/(A1×m2) And calculating the content of the chloroindoxyl in the sample to be detected.
2. The analytical method of claim 1, wherein the solvent is at least one of N, N-dimethylformamide and methanol.
3. The analytical method of claim 1, wherein the chromatographic column is packed with octadecylsilane chemically bonded silica having a particle size of 5 μm.
4. The assay of claim 1, wherein the volume of each injection is 5 μ L.
5. The assay of claim 1, wherein the mobile phase flow rate is 1 mL/min.
6. The assay of claim 1, wherein the chloroindole hydrazide has a detection wavelength of 270 nm.
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| CN110622982A (en) * | 2019-08-21 | 2019-12-31 | 京博农化科技有限公司 | Sterilization composition containing zhongshengmycin |
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| JP2009525337A (en) * | 2006-01-30 | 2009-07-09 | エクセリクシス， インク． | 4-Aryl-2-amino-pyrimidines or 4-aryl-2-aminoalkyl-pyrimidines as JAK-2 modulators and methods of use |
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| WO2008124085A2 (en) * | 2007-04-03 | 2008-10-16 | Exelixis, Inc. | Methods of using combinations of mek and jak-2 inhibitors |
| CN110622982A (en) * | 2019-08-21 | 2019-12-31 | 京博农化科技有限公司 | Sterilization composition containing zhongshengmycin |
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| 4种药剂对番茄黄化曲叶病毒病的田间防效;冯晓菲等;《湖南农业科学》;20191231(第12期);48-50 * |
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