CN115128202A - Method for measuring content of topramezone intermediate - Google Patents

Method for measuring content of topramezone intermediate Download PDF

Info

Publication number
CN115128202A
CN115128202A CN202210897550.2A CN202210897550A CN115128202A CN 115128202 A CN115128202 A CN 115128202A CN 202210897550 A CN202210897550 A CN 202210897550A CN 115128202 A CN115128202 A CN 115128202A
Authority
CN
China
Prior art keywords
sample
standard
methylsulfonyl
bromo
methyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN202210897550.2A
Other languages
Chinese (zh)
Inventor
许慧斌
许百红
李兰兰
杨清
王玉莹
张晓会
刘亚鲁
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Jingbo Agrochemicals Technology Co Ltd
Original Assignee
Jingbo Agrochemicals Technology Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Jingbo Agrochemicals Technology Co Ltd filed Critical Jingbo Agrochemicals Technology Co Ltd
Priority to CN202210897550.2A priority Critical patent/CN115128202A/en
Publication of CN115128202A publication Critical patent/CN115128202A/en
Pending legal-status Critical Current

Links

Images

Classifications

    • 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
    • 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
    • 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
    • G01N30/89—Inverse chromatography

Landscapes

  • Physics & Mathematics (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Analytical Chemistry (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Immunology (AREA)
  • Pathology (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)

Abstract

The invention relates to the technical field of chemical analysis, in particular to a content determination method of topramezone intermediate. The topramezone intermediate is 3-bromo-2-methyl-6-methylsulfonyl-alpha-chlorobenzaldehyde oxime, and the content determination method 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) and (2) analyzing the standard sample and the sample obtained in the step (1) by adopting a reversed-phase high performance liquid chromatography analysis method, wherein the chromatographic column is a chromatographic column VP-ODS, the mobile phase is a mixed system of acetonitrile and glacial acetic acid water solution, the flow rate of the mobile phase is 0.5-1.5 mL/min, the detection wavelength is 254-270 nm, and the mass fraction of the 3-bromo-2-methyl-6-methylsulfonyl-alpha-chlorobenzaldehyde oxime in the sample to be detected is calculated according to an external standard method formula. The method has the advantages of strong specificity, good precision and high recovery rate, and is suitable for quality control of pesticide intermediate products.

Description

Content determination method of topramezone intermediate
Technical Field
The invention relates to the technical field of chemical analysis, in particular to a content determination method of topramezone intermediate. In particular, the method is used for detecting the content of 3-bromo-2-methyl-6-methylsulfonyl-alpha-chlorobenzaldehyde oxime.
Background
Topramezone is the first benzyl ester pyrazolone herbicide discovered and developed by basf corporation, has the characteristics of high safety, excellent selectivity, broad-spectrum herbicidal activity, long time effect, strong compatibility and the like, is the corn field herbicide with the highest safety, and is one of the herbicides with the lowest toxicity to mammals.
The 3-bromo-2-methyl-6-methylsulfonyl-alpha-chlorobenzaldehyde oxime is an important intermediate for synthesizing topramezone, and the structure is shown as a formula (I). In order to accurately determine the content of 3-bromo-2-methyl-6-methylsulfonyl-alpha-chlorobenzaldehyde oxime in the production process and effectively guide the adjustment of process parameters in a workshop, it is necessary to develop a quantitative detection method for 3-bromo-2-methyl-6-methylsulfonyl-alpha-chlorobenzaldehyde oxime.
Figure BDA0003769540220000011
Disclosure of Invention
Aiming at the technical blank of the existing method for detecting the content of 3-bromo-2-methyl-6-methylsulfonyl-alpha-chlorobenzaldehyde oxime, the invention provides a method for detecting the content of 3-bromo-2-methyl-6-methylsulfonyl-alpha-chlorobenzaldehyde oxime by using a high performance liquid chromatography, and the method has the advantages of strong specificity, good precision and high recovery rate, and is suitable for quality control of intermediate products of pesticides.
The technical scheme of the invention is as follows:
a method for measuring the content of a topramezone intermediate, wherein the topramezone intermediate is 3-bromo-2-methyl-6-methylsulfonyl-alpha-chlorobenzaldehyde oxime, 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) and (2) analyzing the standard sample and the sample obtained in the step (1) by adopting a reversed-phase high performance liquid chromatography analysis method, wherein the chromatographic column is a chromatographic column VP-ODS, the mobile phase is a mixed system of acetonitrile and glacial acetic acid water solution, the flow rate of the mobile phase is 0.5-1.5 mL/min, the detection wavelength is 254-270 nm, and the mass fraction of the 3-bromo-2-methyl-6-methylsulfonyl-alpha-chlorobenzaldehyde oxime in the sample to be detected is calculated according to an external standard method formula.
Further, the column length of the column was 150mm, the column inner diameter was 4.6mm, and the column particle size was 5 μm.
Furthermore, the temperature of the chromatographic column is 35-50 ℃, and preferably 40 ℃.
Further, the concentration of the glacial acetic acid in water was 0.8% by volume.
Further, the volume ratio of acetonitrile to glacial acetic acid aqueous solution is 50: 50.
further, the flow rate of the mobile phase was 1 mL/min.
Further, 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, in order to achieve better detection effect and accuracy, the volume of the sample fed in each time is 1-10 μ L, preferably 5 μ L.
Further, the external standard method formula is as follows:
Figure BDA0003769540220000021
in the formula, A 1 -the average value of the peak area of the 3-bromo-2-methyl-6-methylsulfonyl-alpha-chlorobenzaldehyde oxime in the standard sample,
A 2 average of the areas of the peaks of the 3-bromo-2-methyl-6-methylsulfonyl- α -chlorobenzaldoxime in the sample,
m 1 -the quality of the standard sample,
m 2 -the mass of the sample to be tested,
P 1 the mass fraction of 3-bromo-2-methyl-6-methylsulfonyl-alpha-chlorobenzaldehyde oxime in the standard sample,
X 1 -mass fraction of 3-bromo-2-methyl-6-methylsulfonyl- α -chlorobenzaldehyde oxime in the sample.
The method for measuring the content of 3-bromo-2-methyl-6-methylsulfonyl-alpha-chlorobenzaldehyde oxime provided by the invention can also be used for quality control of intermediate products of topramezone technical.
The invention has the beneficial effects that:
the method for measuring the content of the 3-bromo-2-methyl-6-methylsulfonyl-alpha-chlorobenzaldehyde oxime fills the technical blank that no corresponding high performance liquid chromatography detection method exists in the prior art, the method for detecting the mass fraction of the 3-bromo-2-methyl-6-methylsulfonyl-alpha-chlorobenzaldehyde oxime has the advantages of good chromatographic peak shape, accurate integral calculation result, good repeatability, more accurate and timely obtained result and high reliability, provides powerful data support for the production of a raw medicine intermediate, is particularly suitable for the quality control of a raw medicine intermediate product, and has important effect and practical significance for ensuring the quality of a final product.
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 standard in example 1.
FIG. 2 is a chromatogram of the sample in example 1.
FIG. 3 is a chromatogram of the standard in example 2.
FIG. 4 is a chromatogram of the sample in example 2.
FIG. 5 is a graph showing the linear relationship at a wavelength of 254nm in the case of the verification example 2.
FIG. 6 is a graph showing the linear relationship at a wavelength of 235nm in the case of the verification example 2.
FIG. 7 is a graph showing the linear relationship at a wavelength of 270nm in the case of the verification example 2.
In FIGS. 1 to 4, the abscissa represents time (min) and the ordinate represents absorbance; in FIGS. 6 to 7, the abscissa represents the concentration (. mu.g/mL), and the ordinate represents the peak area.
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
In the production, 360 kg of 3-bromo-2-methyl-6-methylsulfonyl-alpha-chlorobenzaldehyde oxime is obtained in 001 batches, and the content of the product is analyzed.
Chromatographic conditions are as follows: a chromatographic column VP-ODS using octadecylsilane chemically bonded silica as a filler has a column length of 150mm, a column inner diameter of 4.6mm, a column particle size of 5 μm, a chromatographic column temperature of 40 ℃, a volume ratio of 50: a mixed system of 50 parts of acetonitrile and 0.8 percent (v/v) of glacial acetic acid aqueous solution is used as a mobile phase, the flow rate of the mobile phase is 1mL/min, the detection wavelength is 254nm, and the injection volume is 5 mu L.
The detection steps are as follows:
(1) accurately weighing 0.0511g of 3-bromo-2-methyl-6-methylsulfonyl-alpha-chlorobenzaldehyde oxime standard sample, placing the standard sample in a 100mL volumetric flask, adding 80mL of methanol, ultrasonically oscillating for dissolution, cooling to room temperature, and diluting to scale with methanol to obtain the standard sample for later use;
accurately weighing 0.0588g of a 3-bromo-2-methyl-6-methylsulfonyl-alpha-chlorobenzaldehyde oxime sample, placing the sample in a 100mL volumetric flask, adding 80mL of methanol, dissolving the sample by ultrasonic oscillation, cooling the solution to room temperature, and diluting the solution to a scale with the methanol to obtain a sample for later use;
(2) after the baseline of the instrument is stable, continuously injecting a plurality of needle samples, calculating the relative response value of each needle, and after the relative response value of two adjacent needles changes by less than 1.5%, sequentially injecting samples according to the sequence of the samples, the sample and the standard sample for detection, wherein the chromatogram is shown in figures 1 and 2, and the data is shown in the following table 1:
table 1 example 1 test results
Figure BDA0003769540220000051
Substituting into external standard method formula
Figure BDA0003769540220000052
In the formula, A 1 -the average value of the peak area of the 3-bromo-2-methyl-6-methylsulfonyl-alpha-chlorobenzaldehyde oxime in the standard sample,
A 2 average of the areas of the peaks of the 3-bromo-2-methyl-6-methylsulfonyl- α -chlorobenzaldoxime in the sample,
m 1 -the quality of the standard sample,
m 2 -the mass of the sample to be tested,
P 1 the mass fraction of 3-bromo-2-methyl-6-methylsulfonyl-alpha-chlorobenzaldehyde oxime in the standard sample,
X 1 -mass fraction of 3-bromo-2-methyl-6-methylsulfonyl- α -chlorobenzaldehyde oxime in the sample;
the mass fraction of 3-bromo-2-methyl-6-methylsulfonyl- α -chlorobenzaldehyde oxime in the sample was calculated to be 92.22%.
Example 2
In the production, 003 batches of 3-bromo-2-methyl-6-methylsulfonyl-alpha-chlorobenzaldehyde oxime is obtained, 400 kg of which is subjected to content analysis.
Chromatographic conditions are as follows: a chromatographic column VP-ODS using octadecylsilane chemically bonded silica as a filler has a column length of 150mm, a column inner diameter of 4.6mm, a column particle size of 5 μm, a chromatographic column temperature of 40 ℃, a volume ratio of 50: a mixed system of 50 parts of acetonitrile and 0.8 percent (v/v) of glacial acetic acid aqueous solution is used as a mobile phase, the flow rate of the mobile phase is 1mL/min, the detection wavelength is 254nm, and the injection volume is 5 mu L.
The detection steps are as follows:
(1) accurately weighing 0.0476g of 3-bromo-2-methyl-6-methylsulfonyl-alpha-chlorobenzaldehyde oxime standard sample, placing the standard sample in a 100mL volumetric flask, adding 80mL of methanol, ultrasonically oscillating for dissolution, cooling to room temperature, and diluting to scale with methanol to obtain the standard sample for later use;
accurately weighing 0.0453g of a 3-bromo-2-methyl-6-methylsulfonyl-alpha-chlorobenzaldehyde oxime sample, placing the 0.0453g in a 100mL volumetric flask, adding 80mL of methanol, ultrasonically oscillating for dissolution, cooling to room temperature, and diluting to a scale with methanol to obtain a sample for later use;
(2) after the baseline of the instrument is stable, continuously injecting a plurality of needle samples, calculating the relative response value of each needle, and after the relative response value of two adjacent needles changes by less than 1.5%, sequentially injecting samples according to the sequence of the samples, the standard samples, the test samples and the standard samples for detection, wherein the chromatogram is shown in figures 3 and 4, and the data is shown in the following table 2:
table 2 example 2 test results
Figure BDA0003769540220000061
The mass fraction of the 3-bromo-2-methyl-6-methylsulfonyl-alpha-chlorobenzaldehyde oxime in the sample is calculated to be 92.73 percent by substituting the formula of an external standard method (the same as the example 1).
Verification example 1 stability test
The sample solution of example 1 was analyzed at two-hour intervals at room temperature, the measurement method and the chromatographic conditions were the same as those of example 1, and the peak area was recorded, and the data are shown in Table 3 below.
TABLE 3 stability test results
Figure BDA0003769540220000062
The RSD is less than 1 percent when the peak areas are compared, which shows that the method has good stability.
Verification example 2 Linear test
A proper amount of 3-bromo-2-methyl-6-methylsulfonyl-alpha-chlorobenzaldehyde oxime standard samples are respectively weighed, methanol is added for dissolution to prepare a group of standard sample solutions with the concentrations of 369 mu g/mL, 463 mu g/mL, 529 mu g/mL, 674 mu g/mL and 749 mu g/mL, the standard sample solutions are sequentially analyzed, the determination method and the chromatographic conditions are the same as those of example 1, and the peak area recording data are shown in the following table 4.
TABLE 4 results of the Linear test
Sample weighing g The concentration of the standard sample is mu g/mL Peak area 1 Peak area 2 Average peak area
0.0369 369 2876903 2880328 2878615.5
0.0463 463 3598892 3601125 3600009
0.0529 529 4132515 4135518 4134016.5
0.0674 674 5251514 5244643 5248078.5
0.0749 749 5838905 5840698 5839801.5
As shown in fig. 5, the peak area was linearly regressed for the sample concentration to obtain a regression equation of y 7792.1x +1476, and the correlation coefficient R was obtained 2 The method is that 1, 3-bromo-2-methyl-6-methylsulfonyl-alpha-chlorobenzaldehyde oxime has a good linear relation within a range of 369-749 mu g/mL, and the method is proved to be in line with the requirement.
In addition to the verification example 2, the detection wavelengths were adjusted, and the linearity verification was performed using 235nm and 270nm as the detection wavelengths, respectively, and the results are shown in tables 5 and 6 and fig. 6 and 7 below.
TABLE 5235 nm wavelength Linear test results
Sample weighing/g Concentration/(μ g/mL) Chromatographic Peak area 1 Chromatographic Peak area 2 Average peak area
0.0369 369 7892681 7898074 7895377.5
0.0463 463 9852367 9857258 9854812.5
0.0529 529 11289380 11301299 11295339.5
0.0674 674 14269716 14294810 14282263
0.0749 749 15833828 15853725 15843776.5
Performing linear regression on the concentration of the sample according to the average peak area obtained by detection to obtain a regression equation under the wavelength of 235 nm:
y＝20917x+187807，R 2 ＝0.9999。
TABLE 6270 nm wavelength Linear test results
Sample weighing/g Concentration/(μ g/mL) Chromatographic Peak area 1 Chromatographic Peak area 2 Average peak area
0.0369 369 3370727 3373363 3372045
0.0463 463 4216320 4221506 4218913
0.0529 529 4840795 4848174 4844484.5
0.0674 674 6146031 6156771 6151401
0.0749 749 6840663 5840698 6843668
And (3) performing linear regression on the concentration of the sample according to the average peak area obtained by detection to obtain a regression equation under the wavelength of 270 nm:
y＝9132.7x+706.47，R 2 ＝1。
it can be seen that at a wavelength of 235nm, although the linear correlation coefficient R 2 The value of (A) is also greater than 0.99, but the intercept is very large, and if the single standard comparison method is adopted for sample analysis, the error is large; correlation coefficient R at 270nm 2 The linear relation of the 1, 3-bromo-2-methyl-6-methylsulfonyl-alpha-chlorobenzaldehyde oxime in the range of 369-749 mu g/mL is good, which shows that the experiment linearity meets the requirement, so that any wavelength can be selected in the range of 254-270 nm for content analysis.
Verification example 3 precision test
Respectively weighing a 3-bromo-2-methyl-6-methylsulfonyl-alpha-chlorobenzaldehyde oxime standard sample and 5 parts of the sample (accurate to 0.0002g) in example 2, respectively placing the standard sample and the sample in a 100mL volumetric flask, adding 80mL of methanol, ultrasonically oscillating and dissolving, cooling to room temperature, and then diluting to a scale with the methanol; the analysis, measurement method and chromatographic conditions were the same as in example 1, and peak areas were recorded, and the data are shown in Table 7 below.
TABLE 7 results of precision test
Figure BDA0003769540220000081
Figure BDA0003769540220000091
And calculating and comparing the content of five parallel samples, wherein the RSD value is less than 1 percent, which shows that the method has good precision.
Verification example 4 recovery test
Separately, a 3-bromo-2-methyl-6-methylsulfonyl- α -chlorobenzaldehyde oxime standard and 5 parts of the sample from example 2 (to an accuracy of 0.0002g) were weighed and different masses of the standard were added to the sample. The chromatographic conditions and assay procedures of example 1 were followed to calculate the recovery of the added standard, and the data are shown in Table 8 below.
TABLE 8 recovery test results
Figure BDA0003769540220000092
As can be seen from Table 8, the recovery rates are all between 98% and 102%, and the average recovery rate is 99.21%, which indicates that the experimental recovery rate meets the requirements.
In conclusion, the method for analyzing the content of the 3-bromo-2-methyl-6-methylsulfonyl-alpha-chlorobenzaldehyde oxime provided by the invention has high accuracy and good operability, and can be widely applied to the analysis and detection of the content of the 3-bromo-2-methyl-6-methylsulfonyl-alpha-chlorobenzaldehyde oxime.
Although the present invention has been described in detail by referring to the drawings in connection with the 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 should be 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 disclosure and the scope of the present invention.

Claims (10)

1. A method for measuring the content of a topramezone intermediate, which is characterized in that the topramezone intermediate is 3-bromo-2-methyl-6-methylsulfonyl-alpha-chlorobenzaldehyde oxime, and the method for measuring the content 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) and (2) analyzing the standard sample and the sample obtained in the step (1) by adopting a reversed-phase high performance liquid chromatography analysis method, wherein the chromatographic column is a chromatographic column VP-ODS, the mobile phase is a mixed system of acetonitrile and glacial acetic acid water solution, the flow rate of the mobile phase is 0.5-1.5 mL/min, the detection wavelength is 254-270 nm, and the mass fraction of the 3-bromo-2-methyl-6-methylsulfonyl-alpha-chlorobenzaldehyde oxime in the sample to be detected is calculated according to an external standard method formula.
2. The method for assaying according to claim 1, wherein the column length of the chromatography column is 150mm, the column inner diameter is 4.6mm, and the column particle size is 5 μm.
3. The method of claim 1, wherein the column temperature is 35 to 50 ℃.
4. The assay of claim 3, wherein the column temperature is 40 ℃.
5. The assay of claim 1, wherein the aqueous glacial acetic acid solution has a concentration of 0.8% by volume.
6. The assay of claim 1, wherein the volume ratio of acetonitrile to aqueous glacial acetic acid is 50: 50.
7. the assay of claim 1, wherein the flow rate of the mobile phase is 1 mL/min.
8. The assay method according to claim 1, wherein the sample is sequentially introduced in the order of standard sample, test sample, and standard sample after the baseline of the apparatus has stabilized.
9. The assay method according to claim 1, wherein the volume of the sample per injection is 1 to 10 μ L.
10. The assay of claim 9, wherein the sample volume per injection is 5 μ L.
CN202210897550.2A 2022-07-28 2022-07-28 Method for measuring content of topramezone intermediate Pending CN115128202A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202210897550.2A CN115128202A (en) 2022-07-28 2022-07-28 Method for measuring content of topramezone intermediate

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202210897550.2A CN115128202A (en) 2022-07-28 2022-07-28 Method for measuring content of topramezone intermediate

Publications (1)

Publication Number Publication Date
CN115128202A true CN115128202A (en) 2022-09-30

Family

ID=83385647

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202210897550.2A Pending CN115128202A (en) 2022-07-28 2022-07-28 Method for measuring content of topramezone intermediate

Country Status (1)

Country Link
CN (1) CN115128202A (en)

Similar Documents

Publication Publication Date Title
CN101101284A (en) Method for simultaneously determining multiple organic acid content of fruit
CN113671077B (en) Method for detecting acryloyl chloride and related substances
CN112697943A (en) Method for analyzing content of 2- (2-methylphenoxymethyl) benzoyl chloride
CN109696509A (en) The remaining method of dimethyl suflfate in a kind of LC-MS detection drug
CN115128202A (en) Method for measuring content of topramezone intermediate
CN112684025B (en) Method for detecting 2-amino-2, 3-dimethylbutyronitrile by high performance liquid chromatography and application thereof
CN113607836B (en) Analysis method for content of indoxacarb key intermediate
CN115684397A (en) Method for determining content of genotoxic impurity hydroxylamine hydrochloride in parecoxib
CN109541059A (en) A method of measurement TCTNB purity
CN112345663B (en) Analysis method for content of 5-chloro-2-methoxycarbonyl-1-indanone ester
CN113607833B (en) Content analysis method of indoxacarb intermediate
CN107271600A (en) The detection method of isomer impurities content in a kind of 4 (3 fluorine benzyloxy) benzaldehydes
CN101650346B (en) Analysis method of content of 2-aminosulfonyl-N,N-dimethylnicotinamide
CN112903834A (en) Detection method for morpholine residue in bulk drug and application thereof
CN114487166B (en) Method for detecting content of 2, 6-dihydroxy-3-cyano-4-trifluoromethylpyridine
CN108760937A (en) Measurement and its application of ethylenediamine are remained in caspofungin acetate
CN114088862A (en) Analysis method for content of 2, 3-dimethyl sulfide
CN114019041B (en) Method for detecting residual amount of triphosgene in industrial waste liquid
CN111398459B (en) Analysis method for content of S- (-) -p-toluenesulfonyl ethyl lactate
CN114965820A (en) Content analysis method of prothioconazole intermediate
CN115901994A (en) Method for analyzing content of flufenacet intermediate
CN101650345A (en) Analysis method of content of 2-chloronicotinic acid
CN115201383B (en) Method for simultaneously determining 5-chloro-2-nitropyridine and isomer thereof
CN117110489A (en) Method for measuring content of topramezone intermediate
CN110988175B (en) Method for determining genotoxic impurity methylglyoxal in cimetidine

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
CB02 Change of applicant information

Address after: 256500 Boxing Economic Development Zone, Shandong, Binzhou

Applicant after: Shandong Jingbo Agrochemical Technology Co.,Ltd.

Address before: 256500 Boxing Economic Development Zone, Shandong, Binzhou

Applicant before: JINGBO AGROCHEMICALS TECHNOLOGY Co.,Ltd.

CB02 Change of applicant information