CN114965820A - Content analysis method of prothioconazole intermediate - Google Patents
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Abstract
The invention relates to the technical field of chemical detection and analysis, and particularly relates to a content analysis method of a prothioconazole intermediate. The prothioconazole intermediate is 2- (1-chlorocyclopropyl) -1- (2-chlorphenyl) -3-hydrazino-2-propanol hydrochloride, and the content analysis method specifically comprises the following steps: (1) using methanol as a solvent to dissolve a standard substance and a sample to be detected respectively, and preparing a standard sample and a test sample; (2) setting the detection wavelength of the high performance liquid chromatography to be 215nm, and mixing the components in a volume ratio of 35-45: taking a mixture system of 65-55 acetonitrile and 0.1% trifluoroacetic acid aqueous solution as a mobile phase, and averaging peak areas of 2- (1-chlorocyclopropyl) -1- (2-chlorphenyl) -3-hydrazino-2-propanol hydrochloride of a standard sample and a sample respectively to obtain an average peak area; and calculating the mass fraction according to a formula. The method has the advantages of strong specificity, good precision and high recovery rate.
Description
Technical Field
The invention relates to the technical field of chemical detection and analysis, and particularly relates to a content analysis method of a prothioconazole intermediate, namely 2- (1-chlorocyclopropyl) -1- (2-chlorphenyl) -3-hydrazino-2-propanol hydrochloride.
Background
Prothioconazole is a novel broad-spectrum triazolethione bactericide, is mainly used for preventing and treating various diseases of crops such as grains, wheat and beans, has the characteristics of low toxicity, no teratogenesis, no toxicity to embryos, safety to people and environment and the like, conforms to the new trend of pesticide development in the 21 st century, and becomes a research hotspot in the pesticide field in recent years.
2- (1-chlorocyclopropyl) -1- (2-chlorphenyl) -3-hydrazino-2-propanol hydrochloride is used as a key intermediate of prothioconazole, and a quantitative detection method of the prothioconazole is still in a blank state at present after relevant documents at home and abroad are examined. The accurate quantification of the method directly influences the next reaction, so that the finding of a simple, convenient and feasible analysis method with high accuracy is an important premise for ensuring the smooth reaction at present.
Based on this, in order to meet the production requirement of the high-quality pesticide technical prothioconazole, a corresponding content analysis detection method needs to be provided.
Disclosure of Invention
Aiming at the technical problem that a quantitative detection method of 2- (1-chlorocyclopropyl) -1- (2-chlorphenyl) -3-hydrazino-2-propanol hydrochloride is still in a blank state, the invention provides a content analysis method, and particularly adopts a reversed phase high performance liquid chromatography analysis method. The method has strong specificity, good precision and high recovery rate, and is particularly suitable for the quality control of intermediate products of the original pesticide, thereby meeting the production requirement of the high-quality original pesticide prothioconazole.
The technical scheme of the invention is as follows:
a content analysis method of a prothioconazole intermediate is 2- (1-chlorocyclopropyl) -1- (2-chlorphenyl) -3-hydrazino-2-propanol hydrochloride, and specifically comprises the following steps:
(1) using methanol as a solvent to dissolve a standard substance and a sample to be detected respectively, and preparing a standard sample and a test sample;
(2) setting the detection wavelength of the high performance liquid chromatography to be 215nm, and mixing the components in a volume ratio of 35-45: a mixture system of 65-55% acetonitrile and 0.1% trifluoroacetic acid water solution is a mobile phase,
respectively averaging the peak areas of the 2- (1-chlorocyclopropyl) -1- (2-chlorphenyl) -3-hydrazino-2-propanol hydrochloride of the standard sample and the sample to obtain the average value of the peak areas;
the mass fraction of 2- (1-chlorocyclopropyl) -1- (2-chlorophenyl) -3-hydrazino-2-propanol hydrochloride was calculated as follows:
in the formula:
A 1 -average of the peak area of 2- (1-chlorocyclopropyl) -1- (2-chlorophenyl) -3-hydrazino-2-propanolate hydrochloride in the standard;
A 2 -average value of peak area for 2- (1-chlorocyclopropyl) -1- (2-chlorophenyl) -3-hydrazino-2-propanolate hydrochloride in the sample;
m 1 -the quality of the standard sample;
m 2 -the mass of the sample;
P 1 -mass fraction of 2- (1-chlorocyclopropyl) -1- (2-chlorophenyl) -3-hydrazino-2-propanol hydrochloride in the sample;
X 1 -mass fraction of 2- (1-chlorocyclopropyl) -1- (2-chlorophenyl) -3-hydrazino-2-propanol hydrochloride in the sample.
Further, the column was a Durashell C18(L) stainless steel column.
Further, the column length of the column was 25 cm.
Furthermore, the chromatographic column uses octadecylsilane chemically bonded silica with a particle size of 5 μm as a filler.
Further, the temperature of the chromatographic column is 38-45 ℃.
Further, the flow rate of the mobile phase is 0.8-1.3 mL/min.
Furthermore, after the baseline of the instrument is stabilized, samples are sequentially introduced according to the sequence of the standard sample, the test sample and the standard sample.
Furthermore, for better detection effect and accuracy, the sample volume of each sample injection is 5 μ L.
The method for detecting the mass fraction of the 2- (1-chlorocyclopropyl) -1- (2-chlorophenyl) -3-hydrazino-2-propanol hydrochloride has the advantages that the method for detecting the mass fraction of the 2- (1-chlorocyclopropyl) -1- (2-chlorophenyl) -3-hydrazino-2-propanol hydrochloride has good chromatographic peak shape, accurate integral calculation result, good repeatability and high reliability of the obtained result, is particularly suitable for quality control of intermediate products of pesticide raw materials, has important action and practical significance on ensuring the quality of final products, obtains the result more accurately and timely, and provides powerful data support for the production of prothioconazole.
Drawings
In order to more clearly illustrate the embodiments or technical solutions in the prior art of the present invention, the drawings used in the description of the embodiments or prior art will be briefly described below, and it is obvious for those skilled in the art that other drawings can be obtained based on these drawings without creative efforts.
FIG. 1 is a chromatogram of the sample obtained in example 1.
FIG. 2 is a chromatogram of a sample from example 1.
FIG. 3 is a chromatogram of the sample obtained in example 2.
FIG. 4 is a chromatogram of a sample from example 2.
FIG. 5 is a chromatogram of a sample taken in comparative example 1.
FIG. 6 is a chromatogram of a sample taken in comparative example 2.
FIG. 7 is a graph showing the linear relationship in the verification example 2.
Detailed Description
In order to make those skilled in the art better understand the technical solution of the present invention, the technical solution in the embodiment of the present invention will be clearly and completely described below with reference to the drawings in the embodiment of the present invention, and it is obvious that the described embodiment is only a part of the embodiment 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.
The following examples used HPLC as LC-20AT infusion pump and SPD-20A UV detector from Shimadzu corporation.
Example 1
A small sample of 20210105 was made to give 59g of a solid which was analyzed for 2- (1-chlorocyclopropyl) -1- (2-chlorophenyl) -3-hydrazino-2-propanol hydrochloride content.
Preparation of standard sample
Accurately weighing 0.0526g of 2- (1-chlorocyclopropyl) -1- (2-chlorphenyl) -3-hydrazino-2-propanol hydrochloride standard sample, placing the standard sample in a 100mL volumetric flask, adding 80mL of methanol, dissolving the mixture by ultrasonic oscillation, cooling the mixture to room temperature, and diluting the mixture to a scale with the methanol to obtain a sample for later use.
Sample preparation
0.0512g of a sample containing 2- (1-chlorocyclopropyl) -1- (2-chlorophenyl) -3-hydrazino-2-propanol hydrochloride is accurately weighed, placed in a 100mL volumetric flask, added with 80mL of methanol, dissolved by ultrasonic oscillation, cooled to room temperature, diluted to the scale with methanol to obtain a sample for later use.
Test and data processing
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, after the relative response value of two adjacent needles is changed by less than 1.5%, the samples are sequentially injected according to the sequence of the standard samples, the test samples and the standard samples, and the volume ratio is 40: 60 parts of acetonitrile: 0.1% trifluoroacetic acid water solution is used as a mobile phase, the flow rate is 1mL/min, the detection wavelength is 215nm, and the sample injection volume is 5 mu L.
Chromatographic column conditions: a chromatographic column Durashell C18(L) using octadecylsilane chemically bonded silica having a particle size of 5 μm as a filler, the column length was 25cm, the number of theoretical plates was 5000, and the column temperature was 40 ℃.
The chromatograms of the standard and sample are shown in fig. 1 and 2, and the data obtained are as follows:
table 1 example 1 test results
Substituting into formula X 1 ＝(A 2 ×m 1 ×P 1 )/(A 1 ×m 2 ) The mass fraction of the sample was calculated to be 98.2%.
Example 2
A small sample of 20211002 lots gave 89g of a solid which was analyzed for 2- (1-chlorocyclopropyl) -1- (2-chlorophenyl) -3-hydrazino-2-propanol hydrochloride content.
Preparation of standard sample
0.0542g of 2- (1-chlorocyclopropyl) -1- (2-chlorophenyl) -3-hydrazino-2-propanol hydrochloride standard sample is accurately weighed, placed in a 100mL volumetric flask, added with 80mL of methanol, dissolved by ultrasonic oscillation, cooled to room temperature, diluted to the scale with methanol to obtain a sample for later use.
Sample preparation
Accurately weighing 0.0534g of a sample containing 2- (1-chlorocyclopropyl) -1- (2-chlorphenyl) -3-hydrazino-2-propanol hydrochloride, placing the sample in a 100mL volumetric flask, adding 80mL of methanol, ultrasonically oscillating to dissolve the sample, cooling the solution to room temperature, and diluting the solution to a scale with the methanol to obtain a sample for later use.
Test and data processing
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, after the relative response value of two adjacent needles is changed by less than 1.5%, the samples are sequentially injected according to the sequence of the standard samples, the test samples and the standard samples, and the volume ratio is 40: 60 parts of acetonitrile: 0.1% trifluoroacetic acid water solution is used as a mobile phase, the flow rate is 1mL/min, the detection wavelength is 215nm, and the sample injection volume is 5 mu L.
Chromatographic column conditions: a chromatographic column Durashell C18(L) using octadecylsilane chemically bonded silica having a particle size of 5 μm as a filler, the column length was 25cm, the number of theoretical plates was 5000, and the column temperature was 40 ℃.
The chromatograms of the standard and sample are shown in fig. 3 and 4, and the data obtained are as follows:
table 2 example 2 test results
Substituting into formula X 1 ＝(A 2 ×m 1 ×P 1 )/(A 1 ×m 2 ) The mass fraction of the sample was calculated to be 97.6%.
To verify the feasibility and accuracy of the method of the invention, the following comparative tests were carried out:
comparative example 1
Weighing 0.0520g of 2- (1-chlorocyclopropyl) -1- (2-chlorophenyl) -3-hydrazino-2-propanol hydrochloride standard substance, placing the standard substance into a 100mL volumetric flask, adding 80mL of methanol, dissolving by ultrasonic oscillation, cooling to room temperature, and diluting to a scale with the methanol to obtain a standard sample solution.
After the machine self-checking is started, and under the specified operating conditions and after the instrument baseline is stable, a plurality of needle standard samples are continuously injected, and the volume ratio of the needle standard samples is 40: 60 parts of acetonitrile: 0.8% glacial acetic acid water solution is used as a mobile phase, the flow rate is 1mL/min, the detection wavelength is 215nm, and the sample injection volume is 5 mu L.
Chromatographic column conditions: a chromatographic column Durashell C18(L) using octadecylsilane chemically bonded silica having a particle size of 5 μm as a filler, the column length was 25cm, the number of theoretical plates was 3000, and the column temperature was 40 ℃.
The chromatogram is shown in fig. 5, and the data obtained are as follows:
table 3 test results of comparative example 1
| 1 | 2 | 3 | 4 | |
| Peak area | 3195730 | 3023131 | 2960627 | 2763128 |
By adopting the detection conditions, the peak area of the sample adsorbed on the chromatographic column is changed greatly, and the content of the detected sample is influenced, so the method is not feasible.
Comparative example 2
Weighing 0.0513g of 2- (1-chlorocyclopropyl) -1- (2-chlorphenyl) -3-hydrazino-2-propanol hydrochloride standard substance, placing the standard substance into a 100mL volumetric flask, adding 80mL of methanol, ultrasonically oscillating for dissolving, cooling to room temperature, and diluting to a scale with the methanol to obtain a standard sample solution.
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 1.2%, the samples are sequentially injected and analyzed according to the sequence of the standard samples, the test samples and the standard samples, and the volume ratio is 40: 60 parts of acetonitrile: 0.1% trifluoroacetic acid water solution is used as a mobile phase, the flow rate is 1mL/min, the detection wavelength is 215nm, and the sample injection volume is 5 mu L.
Chromatographic column conditions: a chromatographic column VP-ODS using octadecylsilane chemically bonded silica as a filler has a column length of 150mm, a theoretical plate number of 3000, and a column temperature of 40 ℃.
The chromatogram is shown in fig. 6, and by adopting the detection conditions, the sample chromatogram has a wide peak and a serious tailing, and a chromatographic column with a sealed end needs to be replaced.
To verify the feasibility and accuracy of the method of the invention, the following verification tests were carried out:
verification example 1 repeatability verification
Preparation of standard sample
0.0511g of 2- (1-chlorocyclopropyl) -1- (2-chlorophenyl) -3-hydrazino-2-propanolate hydrochloride standard substance are weighed and placed in a 100mL volumetric flask, 80mL of methanol is added, ultrasonic oscillation is carried out for dissolution, and after cooling to room temperature, methanol is used for dilution to the scale mark to obtain a standard sample.
Sample preparation
6 parts of 2- (1-chlorocyclopropyl) -1- (2-chlorphenyl) -3-hydrazino-2-propanol hydrochloride sample is weighed, respectively placed in a 100mL volumetric flask, added with 80mL of methanol, dissolved by ultrasonic oscillation, cooled to room temperature, diluted to the scale with the methanol, and 6 groups of parallel samples are obtained.
Test and data processing
After the machine-on self-test was passed, the baseline of the instrument was stabilized under the specified operating conditions, and then the measurement was performed at a wavelength of 215nm, and the chromatographic conditions were the same as in example 1.
According to formula X 1 ＝(A 2 ×m 1 ×P 1 )/(A 1 ×m 2 ) And calculating the content of 2- (1-chlorocyclopropyl) -1- (2-chlorphenyl) -3-hydrazino-2-propanol hydrochloride 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 repeatability.
Table 4 verification example 1 test results
Verification example 2 verification of Linear relationship
Weighing 2- (1-chlorocyclopropyl) -1- (2-chlorophenyl) -3-hydrazino-2-propanol hydrochloride standard substance, placing the standard substance into a 100mL volumetric flask, adding 80mL of methanol, dissolving the solution by ultrasonic oscillation, cooling the solution to room temperature, and diluting the solution to the scale with the methanol to obtain a group of 2- (1-chlorocyclopropyl) -1- (2-chlorophenyl) -3-hydrazino-2-propanol hydrochloride samples with the concentrations of 0.272mg/mL, 391mg/mL, 457mg/mL, 528mg/mL and 691 mg/mL.
After the machine self-test was started, the measurement was carried out at a wavelength of 215nm under the specified operating conditions and after the baseline of the instrument had stabilized, and the chromatographic conditions were the same as in example 1.
The results are shown in Table 5 below.
Table 5 verification example 2 test results
| Serial number | Sample weighing g | Concentration mg/mL | Peak area 1 | Peak area 2 | Average peak area |
| 1 | 0.0272 | 0.272 | 1687452 | 1683408 | 1685430 |
| 2 | 0.0391 | 0.391 | 2417863 | 2412825 | 2415344 |
| 3 | 0.0457 | 0.457 | 2824968 | 2831050 | 2828009 |
| 4 | 0.0528 | 0.528 | 3264237 | 3272549 | 3268393 |
| 5 | 0.0691 | 0.691 | 4280412 | 4279073 | 4279742.5 |
The peak area was used for linear regression of the sample concentration, as shown in FIG. 7, resulting in a regression equation of y 6196113.4350x-3158.1651, R 2 The p-2- (1-chlorocyclopropyl) -1- (2-chlorophenyl) -3-hydrazino-2-propanolate hydrochloride was found to be in good linear relationship within the range of 200 to 700. mu.g/mL at 1.0000.
Verification example 3 verification of precision
Different personnel accurately weigh 6 parts of 2- (1-chlorocyclopropyl) -1- (2-chlorphenyl) -3-hydrazino-2-propanol hydrochloride (accurate to 0.0002g) sample, respectively place the sample in a 100mL volumetric flask, add 80mL of methanol, dissolve the sample by ultrasonic oscillation, cool the solution to room temperature, dilute the solution to the scale with methanol, and obtain a group of samples for intermediate precision test.
After the machine self-test was started, the measurement was carried out at a wavelength of 215nm under the specified operating conditions and after the baseline of the instrument had stabilized, and the chromatographic conditions were the same as in example 1.
According to formula X 1 ＝(A 2 ×m 1 ×P 1 )/(A 1 ×m 2 ) And calculating the content of 2- (1-chlorocyclopropyl) -1- (2-chlorphenyl) -3-hydrazino-2-propanol hydrochloride in 6 groups of samples to be detected, wherein the results are shown in the following table 6, which indicates that the method has good precision.
Table 6 verification example 3 test results
Verification example 4 verification of stability
Weighing 0.0527g (accurate to 0.0002g) of 2- (1-chlorocyclopropyl) -1- (2-chlorophenyl) -3-hydrazino-2-propanol hydrochloride, placing the weighed mass in a 100mL volumetric flask, adding 80mL of methanol, dissolving the solution by ultrasonic oscillation, cooling the solution to room temperature, and diluting the solution to the scale with methanol to obtain a group of samples for time stability test.
After the machine self-checking is passed, under the specified operation condition and after the instrument base line is stabilized, the sample is respectively injected at 0, 1, 2, 4, 8 and 24h, the measurement is carried out at the wavelength of 215nm, and the chromatographic condition is the same as that of the example 1.
The results are shown in Table 7 below, which shows that the method of the present invention is excellent in stability with time.
Table 7 verification example 4 test results
| Time | 0h | 1h | 2h | 4h | 8h | 24h | RSD％ |
| Peak area | 3256676 | 3254450 | 3257506 | 3253312 | 3255189 | 3253364 | 0.07 |
Verification example 5 Bidding recovery Rate verification
20210105 batches of the small samples in example 1 are taken, 0.0526g of the standard sample is weighed, five samples to be detected with different masses are respectively weighed, and the standard samples with different masses are added.
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 215nm, and the chromatographic condition is the same as that of the example 1;
the detection results are shown in the following table 8, the recovery rates of the added standard samples are calculated to be between 98% and 102%, and the average recovery rate is 99.13%, which indicates that the experimental recovery rate meets the requirements, and indicates that the method of the invention has good recovery rate of the added standard samples.
Table 8 verification example 5 test results
Although the present invention has been described in detail in connection with the preferred embodiments with reference to the accompanying drawings, 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 (8)
1. A method for analyzing the content of a prothioconazole intermediate is characterized in that the prothioconazole intermediate is 2- (1-chlorocyclopropyl) -1- (2-chlorphenyl) -3-hydrazino-2-propanol hydrochloride, and the method for analyzing the content specifically comprises the following steps:
(1) using methanol as a solvent to dissolve a standard substance and a sample to be detected respectively, and preparing a standard sample and a test sample;
(2) setting the detection wavelength of the high performance liquid chromatography to be 215nm, and mixing the components in a volume ratio of 35-45: a mixture system of 65-55% acetonitrile and 0.1% trifluoroacetic acid water solution is a mobile phase,
respectively averaging the peak areas of the 2- (1-chlorocyclopropyl) -1- (2-chlorphenyl) -3-hydrazino-2-propanol hydrochloride of the standard sample and the sample to obtain the average value of the peak areas;
the mass fraction of 2- (1-chlorocyclopropyl) -1- (2-chlorophenyl) -3-hydrazino-2-propanol hydrochloride was calculated as follows:
in the formula:
A 1 in the sample, 2- (1-chlorocyclopropyl) -1- (2-chloro)Average of peak areas for phenyl) -3-hydrazino-2-propanoate hydrochloride;
A 2 -average value of peak area for 2- (1-chlorocyclopropyl) -1- (2-chlorophenyl) -3-hydrazino-2-propanolate hydrochloride in the sample;
m 1 -the quality of the standard sample;
m 2 -the mass of the sample;
P 1 -mass fraction of 2- (1-chlorocyclopropyl) -1- (2-chlorophenyl) -3-hydrazino-2-propanol hydrochloride in the sample;
X 1 -mass fraction of 2- (1-chlorocyclopropyl) -1- (2-chlorophenyl) -3-hydrazino-2-propanol hydrochloride in the sample.
2. The assay of claim 1 wherein the chromatographic column is a Durashell C18(L) stainless steel column.
3. The content analysis method according to claim 2, wherein the column length of the chromatography column is 25 cm.
4. The content analysis method according to claim 2, wherein the column is packed with octadecylsilane chemically bonded silica having a particle size of 5 μm.
5. The content analysis method according to claim 1, wherein the column temperature is 38 to 45 ℃.
6. The content analysis method according to claim 1, wherein the flow rate of the mobile phase is 0.8 to 1.3 mL/min.
7. The content analysis method according to claim 1, wherein the sample is sequentially introduced in the order of standard sample, test sample and standard sample after the instrument baseline is stabilized.
8. The assay of claim 1, wherein the sample volume per injection is 5 μ L.
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