CN104020223A - Method for analyzing mass fraction of S-methoprene - Google Patents
Method for analyzing mass fraction of S-methoprene Download PDFInfo
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Abstract
The invention discloses a method for analyzing the mass fraction of S-methoprene. The method comprises the determination of methoprene total ester (anti-form) content, an S-methoprene (S/R) proportion and mass fraction of S-methoprene. The method comprises the following steps: dissolving a sample with methylbenzene, carrying out gas chromatography separation and determination on methoprene in the sample by a capillary chromatographic column using 5% of phenyl and 95% of methylpolysilicone as stationary liquid and an FID detector, and calculating by an external standard method to obtain the methoprene total ester (anti-form) content; and dissolving the sample with normal hexane, carrying out chiral chromatography separation and determination on methoprene in the sample by a chiral liquid chromatographic column and a positive-phase elution system, and determining the S-methoprene (S/R) proportion according to peak area percentage. The product of the methoprene total ester (anti-form) content and the S body proportion in S-methoprene is the mass fraction of S-methoprene.
Description
Technical field
The present invention relates to analysis field, particularly relate to a kind of analytical approach of S-methoprene massfraction.
Background technology
S-methoprene ［ CAS:65733-16-6 ］, belongs to corpus allatum hormone analog, and structural formula is as follows:
S-methoprene belongs to insect growth regulator, IGR, and it does not directly kill larva or adult with toxicity, but acts on larva with juvenile hormone, and larva will rest on the worm pupa stage, can not successfully sprout wings and become adult.In view of the above-mentioned mechanism of action, the growth course of insect is suppressed, to reach deinsectization object.This product is applicable to mosquito, horn fly, and flea, louse, the control of grain storage pest, and effectively used and reached 30 years abroad.
In S-methoprene structure, 7 have 1 chiral center, and 2 two keys exist cis-trans-isomer, and 4 two keys exist with transconfiguration, and the trans isomerization that is transformed into cis very easily occurs 2 cis-trans isomerism types.
4 isomers tables specific as follows of S-methoprene:
In 4 isomerss, only having S-methoprene (trans) for effective ingredient, is also the S-methoprene of indication of the present invention.
Summary of the invention
An analytical approach for S-methoprene massfraction, is characterized in that: comprise following mensuration:
1) mensuration of the total ester of methoprene (trans) content
Sample dissolves with toluene, use capillary chromatographic column and fid detector that 5% phenyl-95% methyl polysiloxane is immobile liquid, methoprene in sample is carried out gas chromatography separation and measured, use external standard method to calculate the total ester of methoprene (trans) content.
2) mensuration of S-methoprene S/R ratio and S-methoprene massfraction
Sample n-hexane dissolution, is used Chiral liquid chromatography post and positive elution system, and the methoprene in sample is carried out chiral chromatogram separation and measured, and according to peak area number percent, determines S-methoprene S/R ratio.In the total ester of methoprene (trans) content and S-methoprene, the product of S body ratio is the massfraction of S-methoprene.
Described 1), its instrument condition:
Gas chromatograph: there is fid detector:
Chromatographic work station:
Chromatographic column: 30m * 0.25mm (i.d) bore capillary column, is coated with 5% phenyl-95% methyl polysiloxane immobile liquid coating of 1.0um thickness:
Ultrasonic oscillator:
Described gas chromatography operating conditions is as follows:
Column temperature: 80 ℃/0 minute-6.5 ℃/min-300 ℃/6 minutes;
Sample introduction temperature: (vaporizer temperature): 280 ℃;
Detected temperatures: (sensing chamber's temperature): 300 ℃;
Carrier gas: High Purity Nitrogen;
Nebulizer gas pressure: 25psi;
Split ratio: 10.2/1;
Air mass flow: 300ml/min;
Hydrogen flowing quantity: 30ml/min;
Sampling volume: 0.1ul;
Relative retention time: methoprene trans-isomer: 1.00;
Methoprene cis-isomer: 0.96.
Described 1) determination step is as follows:
The preparation of A, standard specimen solution:
Take 0.5g S-methoprene standard model, with dilution with toluene constant volume, to 10ml, ultrasonic concussion 1min is standby.
The preparation of B, sample solution:
Take 0.5g S-methoprene specimen sample, with dilution with toluene constant volume, to 10ml, ultrasonic concussion 1min is standby.
C, mensuration:
Under aforesaid operations condition, after instrument baseline stability, inject continuously number pin mark sample solution, until phase
Connect two pins, methoprene (trans) peak area relatively changes and is less than 5%, first injects toluene solvant as blank, then according to standard specimen solution, sample solution, sample solution, standard specimen solution, sequentially tests.
Described 1) the total ester of methoprene (trans) cubage is as follows:
A, the total ester of methoprene (trans) content C
(total ester)(%), by formula (1), calculate:
In formula:
A
1: the total ester of methoprene (trans) peak area in standard model;
A
2: the total ester of methoprene (trans) peak area in test sample;
M
1: the weigh of standard model;
M
2: the weigh of test sample;
T: the total ester of methoprene (trans) content of standard model, %, known quality mark;
Described 2), in, its instrument condition is:
High performance liquid chromatograph: there is variable wavelength UV detecting device;
Chromatographic work station;
The stainless steel column of chromatographic column: 250mm * 4.6mm (i.d), in-built Daicel chiralpak AD-H silica, 5um filling material;
Ultrasonator.
The operating conditions of described liquid chromatography:
Mobile phase: count by volume: normal hexane/isopropyl alcohol=100/0.5;
Flow: 0.5ml/min;
Detect wavelength: 254nm;
Column temperature: 25 ℃;
Sampling volume: 10.0ul;
Relative retention time: S-methoprene: 1.00;
R-methoprene: 1.06;
Described 2) determination step:
The preparation of A, standard specimen solution:
Take 20mgS-methoprene standard model, with mobile phase, dilute constant volume to 10 ml, then draw this solution 0.1ml, still with mobile phase, dilute constant volume to 10ml, ultrasonic concussion 1min, standby;
The preparation of B, sample solution:
Take 20mgS-methoprene testing sample, with mobile phase, dilute constant volume to 10ml, then draw this solution 0.1ml, still with mobile phase, dilute constant volume to 10ml, ultrasonic concussion 1min, standby;
C, mensuration:
Under aforesaid operations condition, after instrument baseline stability, inject continuously number pin mark sample solution, until two pins that are connected, S-methoprene peak area relatively changes and is less than 5%, according to standard specimen solution, sample solution, sample solution, standard specimen solution, sequentially tests.
Described 2) being calculated as follows of S-methoprene massfraction and methoprene S/R ratio E in:
(1) S-methoprene massfraction C
(S-methoprene)(%), by formula (3), calculate:
In formula:
AS:S-methoprene peak area;
AR:R-methoprene peak area;
C (total ester): the total ester of methoprene (trans) content;
(2) methoprene S/R ratio E, calculates by formula (4):
In formula:
QS:S-methoprene peak area ratio, QS=AS/ (AS+AR) * 100%;
QR:R-methoprene peak area ratio, QR=AR/ (AS+AR) * 100%.
Beneficial effect of the present invention is:
The invention provides a kind of analytical approach of S-methoprene massfraction, the method is by the effective constituent of S-methoprene, and impurity has carried out thorough anatomy, has the pioneering meaning in the world.Meanwhile, the clear and definite composition of S-methoprene, produces instructing, and system product standard provides strong foundation.
Accompanying drawing explanation
Fig. 1 is methoprene gas chromatogram;
Fig. 2 is racemization methoprene chiral separation liquid chromatography figure;
Fig. 3 is S-methoprene chiral separation liquid chromatography figure;
Fig. 4 is S-methoprene gas phase analysis linear graph.
Specific embodiment
Below by specific embodiment, the present invention is described in detail.
embodiment 1
One, instrument condition
1, instrument configuration:
Gas chromatograph: there is fid detector;
Chromatographic work station;
Chromatographic column: 30m * 0.25mm (i.d) bore capillary column, is coated with 5% phenyl-95% methyl polysiloxane immobile liquid coating of 1.0um thickness;
Ultrasonic oscillator.
2, chromatographic condition:
Column temperature: 80 ℃/0 minute-6.5 ℃/min-300 ℃/6 minutes;
Sample introduction temperature: (vaporizer temperature): 280 ℃;
Detected temperatures: (sensing chamber's temperature): 300 ℃;
Carrier gas: High Purity Nitrogen;
Nebulizer gas pressure: 25psi;
Split ratio: 10.2/1;
Air mass flow: 300ml/min;
Hydrogen flowing quantity: 30ml/min;
Sampling volume: 0.1ul;
One, system suitability test
1, sample preparation:
Accurately take the S-methoprene standard model of 500mg (being accurate to 0.1mg), use dilution with toluene constant volume to 10mL.
2, sample introduction:
By the standard model solution preparing continuous sample introduction three times under the chromatographic condition of regulation, record S-methoprene each time goes out peak retention time and peak area, carries out system suitability test.
Two, linear relationship
1, sample preparation:
Take the S-methoprene standard model of following weight, use dilution with toluene constant volume to 10mL, and identified as samples is designated as to X1 ~ X6;
350mg，400mg，450mg，500mg，550mg，600mg；
2, six samples of sample introduction: X1 ~ X6 are sample introduction respectively, twice of each sample feeding;
3, sample introduction record
4, interpretation of result
Linear analysis result shows, S-methoprene sample concentration has the good range of linearity between 35.12 ~ 59.93g/L.Equation of linear regression is Y=581.68X-9582.5, coefficient R=0.9997.
Three, the confirmation of accuracy
1, sample preparation
Within the scope of 350 ~ 600mg, take at random the S-methoprene standard model of constant weight, use dilution with toluene constant volume to 10mL, and identified as samples is designated as to Z1 ~ Z6;
Choose X4 solution as standard solution;
2, six samples of sample introduction: Z1 ~ Z6 are sample introduction respectively, and each sample feeding twice, according to the order sample introduction of a pin standard solution, two sample needle solution, a pin standard solution;
3, sample introduction record
4, interpretation of result
The gained recovery, between 99.0% ~ 101.0%, meets accuracy and confirms requirement;
Four, the confirmation of system precision
1, sample preparation
Take six test samples, example weight is 500mg, uses dilution with toluene constant volume to 10mL, and identified as samples is designated as to J1 ~ J6; Choose X4 solution as standard solution;
2, six samples of sample introduction: J1 ~ J6 are sample introduction respectively, each sample feeding twice, and the order sample introduction according to a pin standard solution, two sample needle solution, a pin standard solution, carries out cubage according to formula;
3, sample introduction record
4. interpretation of result
Relative standard deviation is 0.13%, shows that the precision of system meets the requirements;
The ratio measuring of S body in S-methoprene:
One, instrument condition
High performance liquid chromatograph: there is variable wavelength UV detecting device;
Chromatographic work station;
The stainless steel column of chromatographic column: 250mm * 4.6mm (i.d), in-built Daicel chiralpak AD-H silica, 5um filling material;
Ultrasonator;
Two, the operating conditions of liquid chromatography:
Mobile phase: normal hexane/isopropyl alcohol=100/0.5 (volume ratio);
Flow: 0.5ml/min;
Detect wavelength: 254nm;
Column temperature: 25 ℃;
Sampling volume: 10.0ul;
Relative retention time: S-methoprene: 1.00;
R-methoprene: 1.06;
Three, determination step:
1, sample preparation
The preparation of A, standard specimen solution
Take 20mgS-methoprene standard model, with mobile phase, dilute constant volume to 10 ml, then draw this solution 0.1ml, still with mobile phase, dilute constant volume to 10ml, ultrasonic concussion 1min, standby;
The preparation of B, test solution
Take respectively the corresponding S-methoprene test of 20mg J1-J6 sample, with mobile phase, dilute constant volume to 10 ml, then draw this solution 0.1ml, still with mobile phase, dilute constant volume to 10ml, ultrasonic concussion 1min, and identified as samples is designated as to S1 ~ S6;
2, sample introduction:
Six samples of S1 ~ S6 are sample introduction respectively, each sample feeding twice, and according to the order sample introduction of a pin standard solution, two sample needle solution, a pin standard solution, direct reference area degree;
3. sample introduction record
S-methoprene massfraction (%)
Claims (7)
1. an analytical approach for S-methoprene massfraction, is characterized in that: comprise following mensuration:
1) mensuration of the total ester of methoprene (trans) content
Sample dissolves with toluene, use capillary chromatographic column and fid detector that 5% phenyl-95% methyl polysiloxane is immobile liquid, methoprene in sample is carried out gas chromatography separation and measured, use external standard method to calculate the total ester of methoprene (trans) content;
The mensuration of S-methoprene S/R ratio and S-methoprene massfraction
Sample n-hexane dissolution, is used Chiral liquid chromatography post and positive elution system, and the methoprene in sample is carried out chiral chromatogram separation and measured, and according to peak area number percent, determines S-methoprene S/R ratio;
In the total ester of methoprene (trans) content and S-methoprene, the product of S body ratio is the massfraction of S-methoprene.
2. the analytical approach of a kind of S-methoprene massfraction according to claim 1, is characterized in that, described 1) in, its instrument condition:
Gas chromatograph: there is fid detector;
Chromatographic work station:
Chromatographic column: 30m * 0.25mm (i.d) bore capillary column, is coated with 5% phenyl-95% methyl polysiloxane immobile liquid coating of 1.0um thickness;
Ultrasonic oscillator;
Described gas chromatography operating conditions is as follows:
Column temperature: 80 ℃/0 minute-6.5 ℃/min-300 ℃/6 minutes;
Sample introduction temperature: (vaporizer temperature): 280 ℃;
Detected temperatures: (sensing chamber's temperature): 300 ℃;
Carrier gas: High Purity Nitrogen;
Nebulizer gas pressure: 25psi;
Split ratio: 10.2/1;
Air mass flow: 300ml/min;
Hydrogen flowing quantity: 30ml/min;
Sampling volume: 0.1ul;
Relative retention time: methoprene trans-isomer: 1.00;
Methoprene cis-isomer: 0.96.
3. the determination step analytical approach of a kind of S-methoprene massfraction according to claim 1, is characterized in that, described 1) is as follows:
The preparation of A, standard specimen solution:
Take 0.5g S-methoprene standard model, with dilution with toluene constant volume, to 10ml, ultrasonic concussion 1min is standby;
The preparation of B, sample solution:
Take 0.5g S-methoprene specimen sample, with dilution with toluene constant volume, to 10ml, ultrasonic concussion 1min is standby;
C, mensuration:
Under aforesaid operations condition, after instrument baseline stability, inject continuously number pin mark sample solution, until phase
Connect two pins, methoprene (trans) peak area relatively changes and is less than 5%, first injects toluene solvant as blank, then according to standard specimen solution, sample solution, sample solution, standard specimen solution, sequentially tests.
4. the analytical approach of a kind of S-methoprene massfraction according to claim 1, is characterized in that, described 1) the total ester of methoprene (trans) cubage is as follows:
A, the total ester of methoprene (trans) content C
(total ester)(%), by formula (1), calculate:
In formula:
A
1: the total ester of methoprene (trans) peak area in standard model;
A
2: the total ester of methoprene (trans) peak area in test sample;
M
1: the weigh of standard model;
M
2: the weigh of test sample;
T: the total ester of methoprene (trans) content of standard model, %, known quality mark.
5. the analytical approach of a kind of S-methoprene massfraction according to claim 1, is characterized in that: described 2), its instrument condition is:
High performance liquid chromatograph: there is variable wavelength UV detecting device;
Chromatographic work station;
The stainless steel column of chromatographic column: 250mm * 4.6mm (i.d), in-built Daicel chiralpak AD-H silica, 5um filling material;
Ultrasonator
The operating conditions of described liquid chromatography:
Mobile phase: count by volume: normal hexane/isopropyl alcohol=100/0.5;
Flow: 0.5ml/min;
Detect wavelength: 254nm;
Column temperature: 25 ℃;
Sampling volume: 10.0ul;
Relative retention time: S-methoprene: 1.00;
R-methoprene: 1.06.
6. the analytical approach of a kind of S-methoprene massfraction according to claim 1, is characterized in that: determination step described 2):
The preparation of A, standard specimen solution:
Take 20mgS-methoprene standard model, with mobile phase, dilute constant volume to 10 ml, then draw this solution 0.1ml, still with mobile phase, dilute constant volume to 10ml, ultrasonic concussion 1min, standby;
The preparation of B, sample solution:
Take 20mgS-methoprene testing sample, with mobile phase, dilute constant volume to 10ml, then draw this solution 0.1ml, still with mobile phase, dilute constant volume to 10ml, ultrasonic concussion 1min, standby;
C, mensuration:
Under aforesaid operations condition, after instrument baseline stability, inject continuously number pin mark sample solution, until two pins that are connected, S-methoprene peak area relatively changes and is less than 5%, according to standard specimen solution, sample solution, sample solution, standard specimen solution, sequentially tests.
7. the analytical approach of a kind of S-methoprene massfraction according to claim 1, is characterized in that: being calculated as follows of S-methoprene massfraction and methoprene S/R ratio E described 2):
(1) S-methoprene massfraction C
(S-methoprene)(%), by formula (3), calculate:
In formula:
AS:S-methoprene peak area;
AR:R-methoprene peak area;
C (total ester): the total ester of methoprene (trans) content;
(2) methoprene S/R ratio E, calculates by formula (4):
In formula:
QS:S-methoprene peak area ratio, QS=AS/ (AS+AR) * 100%;
QR:R-methoprene peak area ratio, QR=AR/ (AS+AR) * 100%.
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Cited By (7)
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| CN106706824A (en) * | 2015-11-16 | 2017-05-24 | 中国科学院大连化学物理研究所 | Method for detecting insect in-vivo juvenile hormone JH II based on chromatography-mass spectrometry |
| CN108279273A (en) * | 2017-12-28 | 2018-07-13 | 常州胜杰化工有限公司 | A kind of HPLC analytical method of S- hydroprenes |
| CN109959730A (en) * | 2017-12-26 | 2019-07-02 | 广东东阳光药业有限公司 | A method of with the related substance of HPLC method measurement methoprene |
| CN112219862A (en) * | 2020-10-13 | 2021-01-15 | 博益德（北京）生物科技有限公司 | Fly and larva killing agent for farm |
| CN114460204A (en) * | 2022-02-15 | 2022-05-10 | 诺安实力可商品检验（青岛）有限公司 | Method for simultaneously detecting cyenopyrafen and methoprene pesticide residues in plant-derived food |
| CN114624365A (en) * | 2022-04-18 | 2022-06-14 | 中国测试技术研究院 | Method for simultaneously determining residues of three methoprene juvenile hormone analogues in tea |
| WO2023123194A1 (en) * | 2021-12-30 | 2023-07-06 | 浙江海正药业股份有限公司 | Analysis method for detecting chiral isomer impurities in methoprene |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106706824A (en) * | 2015-11-16 | 2017-05-24 | 中国科学院大连化学物理研究所 | Method for detecting insect in-vivo juvenile hormone JH II based on chromatography-mass spectrometry |
| CN106706824B (en) * | 2015-11-16 | 2018-04-13 | 中国科学院大连化学物理研究所 | The detection method of juvenile hormone JH II in a kind of insect bodies of application of gas chromatorgraphy/mass |
| CN109959730A (en) * | 2017-12-26 | 2019-07-02 | 广东东阳光药业有限公司 | A method of with the related substance of HPLC method measurement methoprene |
| CN108279273A (en) * | 2017-12-28 | 2018-07-13 | 常州胜杰化工有限公司 | A kind of HPLC analytical method of S- hydroprenes |
| CN112219862A (en) * | 2020-10-13 | 2021-01-15 | 博益德（北京）生物科技有限公司 | Fly and larva killing agent for farm |
| WO2023123194A1 (en) * | 2021-12-30 | 2023-07-06 | 浙江海正药业股份有限公司 | Analysis method for detecting chiral isomer impurities in methoprene |
| CN114460204A (en) * | 2022-02-15 | 2022-05-10 | 诺安实力可商品检验（青岛）有限公司 | Method for simultaneously detecting cyenopyrafen and methoprene pesticide residues in plant-derived food |
| CN114624365A (en) * | 2022-04-18 | 2022-06-14 | 中国测试技术研究院 | Method for simultaneously determining residues of three methoprene juvenile hormone analogues in tea |
| CN114624365B (en) * | 2022-04-18 | 2023-08-08 | 中国测试技术研究院 | Method for simultaneously determining residues of three methoprene juvenile hormone analogues in tea |
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