CN113552115A - Method for rapidly detecting azoxystrobin by utilizing illumination and surface enhanced Raman spectroscopy - Google Patents
Method for rapidly detecting azoxystrobin by utilizing illumination and surface enhanced Raman spectroscopy Download PDFInfo
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- 239000005730 Azoxystrobin Substances 0.000 title claims abstract description 32
- WFDXOXNFNRHQEC-GHRIWEEISA-N azoxystrobin Chemical compound CO\C=C(\C(=O)OC)C1=CC=CC=C1OC1=CC(OC=2C(=CC=CC=2)C#N)=NC=N1 WFDXOXNFNRHQEC-GHRIWEEISA-N 0.000 title claims abstract description 32
- 238000000034 method Methods 0.000 title claims abstract description 25
- 238000005286 illumination Methods 0.000 title claims abstract description 13
- 238000004416 surface enhanced Raman spectroscopy Methods 0.000 title abstract description 7
- 238000001069 Raman spectroscopy Methods 0.000 claims abstract description 17
- 238000002156 mixing Methods 0.000 claims abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 10
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 10
- 239000010931 gold Substances 0.000 claims description 10
- 229910052737 gold Inorganic materials 0.000 claims description 10
- 229910052700 potassium Inorganic materials 0.000 claims description 10
- 239000011591 potassium Substances 0.000 claims description 10
- 239000001509 sodium citrate Substances 0.000 claims description 10
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 claims description 10
- 229940038773 trisodium citrate Drugs 0.000 claims description 10
- 238000010438 heat treatment Methods 0.000 claims description 8
- 235000013399 edible fruits Nutrition 0.000 claims description 7
- 235000013311 vegetables Nutrition 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 6
- 238000000605 extraction Methods 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 238000002137 ultrasound extraction Methods 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 238000003841 Raman measurement Methods 0.000 claims description 2
- 238000012512 characterization method Methods 0.000 claims description 2
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000001514 detection method Methods 0.000 abstract description 9
- 238000006303 photolysis reaction Methods 0.000 abstract description 5
- 230000015843 photosynthesis, light reaction Effects 0.000 abstract description 5
- 238000001237 Raman spectrum Methods 0.000 abstract description 4
- 238000004458 analytical method Methods 0.000 abstract description 3
- 230000035945 sensitivity Effects 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 238000005516 engineering process Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 20
- 230000000694 effects Effects 0.000 description 3
- 235000012055 fruits and vegetables Nutrition 0.000 description 3
- 229940038487 grape extract Drugs 0.000 description 3
- 239000012086 standard solution Substances 0.000 description 3
- 238000000479 surface-enhanced Raman spectrum Methods 0.000 description 3
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000010355 oscillation Effects 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- XERJKGMBORTKEO-VZUCSPMQSA-N (1e)-2-(ethylcarbamoylamino)-n-methoxy-2-oxoethanimidoyl cyanide Chemical compound CCNC(=O)NC(=O)C(\C#N)=N\OC XERJKGMBORTKEO-VZUCSPMQSA-N 0.000 description 1
- -1 2-cyanophenoxy Chemical group 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- 240000008067 Cucumis sativus Species 0.000 description 1
- 235000009849 Cucumis sativus Nutrition 0.000 description 1
- 239000005756 Cymoxanil Substances 0.000 description 1
- 241000221785 Erysiphales Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 241000257303 Hymenoptera Species 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 241000233679 Peronosporaceae Species 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 241000219094 Vitaceae Species 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- BAPJBEWLBFYGME-UHFFFAOYSA-N acrylic acid methyl ester Natural products COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 238000012271 agricultural production Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000010504 bond cleavage reaction Methods 0.000 description 1
- 230000007665 chronic toxicity Effects 0.000 description 1
- 231100000160 chronic toxicity Toxicity 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- BSDQITJYKQHXQR-UHFFFAOYSA-N methyl prop-2-eneperoxoate Chemical compound COOC(=O)C=C BSDQITJYKQHXQR-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000007699 photoisomerization reaction Methods 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N21/00—Investigating or analysing materials by the use of optical means, i.e. using sub-millimetre waves, infrared, visible or ultraviolet light
- G01N21/62—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light
- G01N21/63—Systems in which the material investigated is excited whereby it emits light or causes a change in wavelength of the incident light optically excited
- G01N21/65—Raman scattering
- G01N21/658—Raman scattering enhancement Raman, e.g. surface plasmons
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Physics & Mathematics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
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- General Physics & Mathematics (AREA)
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- Pathology (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
Abstract
The invention provides a method for rapidly detecting azoxystrobin by utilizing illumination and surface enhanced Raman spectroscopy, belonging to the field of substance analysis and detection. The method comprises the steps of carrying out ultraviolet irradiation on a solution containing a target object for a certain time, mixing the solution with a surface enhanced reagent, and testing by adopting a surface enhanced Raman technology. The invention confirms the existence of the azoxystrobin by detecting a newly added characteristic peak of a photolysis product of the azoxystrobin, the characteristic peak appears in a silent zone of a general Raman spectrum, and 2230cm is innovatively detected‑1The Raman peak at (A) is taken as a qualitative and quantitative characteristic peak. The method has the advantages of sensitivity, simplicity and low cost.
Description
Technical Field
The invention belongs to the field of substance analysis and detection, and particularly relates to the technical field of rapid detection of environmental and food safety. In particular to a method for rapidly detecting azoxystrobin by utilizing illumination and surface enhanced Raman spectroscopy.
Background
Azoxystrobin (azoxystrobin, (E) - [2- [6- (2-cyanophenoxy) pyrimidin-4-yloxy ] phenyl ] -3-methoxy methyl acrylate) is a methoxy acrylate fungicide synthesized by Junda corporation of Switzerland at the end of the 20 th century. The composition has effect in inhibiting fungi respiration, and can destroy energy synthesis of thallus. The azoxystrobin has the advantages of high targeting property, long effective period of action, high activity and the like, so that the azoxystrobin is widely applied to the control of diseases of crops such as cucumbers, grapes, rice, tomatoes, potatoes and the like in agricultural production in China. The bactericidal composition has broad-spectrum bactericidal activity and can achieve good control effects on most fungal diseases such as rice blast, downy mildew, stinking smut, net blotch, rust disease, powdery mildew and the like. Azoxystrobin has low acute and chronic toxicity to humans, birds, mammals and bees, but it is extremely toxic to aquatic invertebrates.
The current detection of azoxystrobin is mainly focused on liquid chromatography. Liquid chromatography has many drawbacks such as susceptibility to solvents, high cost, and long analysis time. The surface enhanced raman spectroscopy is increasingly applied to food detection because of the capability of amplifying fingerprint information, and has the characteristics of higher sensitivity, high result output speed and the like.
Disclosure of Invention
The invention aims to provide a method for rapidly detecting azoxystrobin by utilizing illumination and surface enhanced Raman spectroscopy. The invention confirms the existence of the azoxystrobin by detecting the photolysis product of the azoxystrobin, and the azoxystrobin solution which is not subjected to photolysis is 2230cm-1No raman signal; the photolyzed azoxystrobin solution, whether it is a photoisomerization reaction or a double bond cleavage, changes the state of the cyano function with the formation of photolysis product, and the changed cyano group is in the silent zone 2230cm-1To generate a stable raman signal. Therefore 2230cm-1Becomes the qualitative characteristic peak of azoxystrobin, thereby realizing rapid detection.
The technical scheme of the invention is as follows:
a method for rapidly detecting azoxystrobin by utilizing illumination and surface enhanced Raman comprises the following steps:
(1) preparing gold sol by adopting a method of reducing potassium chloroaurate with trisodium citrate: stirring and heating the potassium chloroaurate solution to boiling, quickly adding trisodium citrate solution, continuously stirring and heating until the color is stable, and stopping to obtain gold sol;
(2) preparation of two solutions to be tested: dissolving the azoxystrobin standard product in an organic solvent to obtain a to-be-detected solution of the azoxystrobin standard product; pretreating the actual sample to obtain a solution to be detected of the actual sample;
(3) photolysis: placing the two solutions to be detected under an ultraviolet light source for irradiation;
(4) raman measurement: setting working parameters of the laser Raman spectrometer: wavelength of laser, laser power and scanning time: respectively mixing the gold sol and the two photolyzed solutions to be detected according to the proportion of 10: 1 or 3: 2, and then detecting;
(5) and (3) characterization: scanning using a laser Raman spectrometer at 2230cm-1The Raman peak at (A) is taken as a qualitative characteristic peak.
The mass percentage concentration of the potassium chloroaurate solution is 0.6%, the mass percentage concentration of the trisodium citrate solution is 0.5% -2.0%, and the volume ratio of the potassium chloroaurate solution to the trisodium citrate solution is 100: 3-8; the heating temperature is 100-150 ℃; stirring at a speed of 300-900 r/min; the heating time is 10-40 min.
The organic solvent is methanol or methanol water.
The actual sample is fruit and vegetable.
The pretreatment process of the actual sample comprises the following steps: cutting 1-10 g of vegetable leaves or fruit skins into pieces, adding an extracting agent, performing oscillation extraction for 10min, performing ultrasonic extraction for 3min, transferring the extract into a volumetric flask, and performing constant volume.
The wavelength of the ultraviolet light source is 302nm or 254nm, and the irradiation time is 10-60 min.
The wavelength of the laser is set to be 785nm, the laser power is set to be 50-300 mW, and the scanning time is set to be 5-30 s.
The invention has the beneficial effects that: the Raman spectrum is divided into fingerprint regions (wave number less than 1800 cm)-1) And a silence region (wave number) 1800cm-1) The most common of them is the information of the fingerprint area, while the silence area is less applied. In the invention, the characteristic peak is analyzed to generate a silent area, and the rich information of the Raman spectrum is utilized more deeply, thereby providing favorable evidence for the theoretical research of the functional group vibration and providing possibility for the subsequent research.
Drawings
FIG. 1 is a surface enhanced Raman spectrum of a 10ppm azoxystrobin methanol solution before and after illumination.
FIG. 2 is a surface enhanced Raman spectrum of azoxystrobin methanol solutions with different concentrations after being irradiated for 20min by a 302nm light source.
FIG. 3 is 2230cm in FIG. 1-1At wave number, different concentrationsPlot of linear relationship between the standard solution of azoxystrobin and peak intensity.
FIG. 4 is a surface enhanced Raman spectrum of a grape extract sprayed with azoxystrobin standard solution before and after illumination.
Detailed Description
The following detailed description of specific embodiments of the present invention is provided in connection with the accompanying drawings.
A novel detection method of azoxystrobin comprises the following steps: firstly, carrying out illumination treatment on a target object containing an object to be detected: thereafter, surface enhanced raman spectroscopy scans were performed: finally, at 2230cm-1The Raman peak at (A) is taken as a qualitative characteristic peak. The method comprises the following steps:
(1) preparing gold sol: a method for reducing potassium chloroaurate by trisodium citrate is adopted, 47mL of ultrapure water and 3mL of potassium chloroaurate (6-10 mg/mL) solution are mixed uniformly, stirred, heated and boiled, and 2mL of trisodium citrate solution (0.5-2.0%) is added rapidly. And continuously keeping the boiling state for 10-40 min until the color is stable, and obtaining the gold sol with a proper particle size.
(2) Setting scanning parameters of the laser Raman spectrometer: an excitation light source is 785nm, the laser power of the instrument is 50-300 mW, and the scanning time is 5-30 s.
Example 1
The azoxystrobin solid powder is prepared into a solution with the concentration of 1000mg/L by methanol, and then is diluted into 0.1, 0.5, 1, 2, 5, 10, 25, 50 and 100mg/L by methanol, and is subpackaged into 2mL centrifuge tubes. Placing the azoxystrobin in the sample under an ultraviolet light source of 302nm for 20in, taking out, mixing with gold sol according to the ratio of 1: 2, and performing Raman spectrum scanning to obtain surface enhanced Raman spectrograms of azoxystrobin with various concentrations, wherein the lowest detection concentration can be as low as 0.5 mg/L. In the range of 0.5-25mg/L, the silent zone is 2230cm-1There is a good linear relationship between the peak intensity and the logarithm of the concentration, and r can reach 0.9880.
Example 2
Cleaning the surface of grape, drying, weighing a proper amount of sample, placing the sample in a beaker, quantitatively dripping 0.5, 1.0 and 5.0mg/kg cymoxanil methanol standard solution on the surface of fruit and vegetable, and placing the fruit and vegetable in a dark environment until the solvent is completely volatilized. Towards the interior of the beakerAdding methanol for extraction, extracting for 10min under oscillation, performing ultrasonic extraction for 3min, transferring the extractive solution into volumetric flask, washing the beaker with small amount of methanol for several times, transferring all the washing solution into volumetric flask, and diluting to desired volume with methanol. Absorbing 2mL of extract liquid, irradiating for 20min under a 302nm ultraviolet light source, taking out, mixing with the gold sol according to the proportion of 1: 2 respectively, and using for Raman detection. The results are shown in FIG. 3. The grape extract after illumination is 2230cm-1There is a clear raman signal, whereas the grape extract without illumination is absent.
Claims (10)
1. A method for rapidly detecting azoxystrobin by utilizing illumination and surface enhanced Raman is characterized by comprising the following steps:
(1) preparing gold sol by adopting a method of reducing potassium chloroaurate with trisodium citrate: stirring and heating the potassium chloroaurate solution to boiling, quickly adding trisodium citrate solution, continuously stirring and heating until the color is stable, and stopping to obtain gold sol;
(2) preparation of two solutions to be tested: dissolving the azoxystrobin standard product in an organic solvent to obtain a to-be-detected solution of the azoxystrobin standard product; pretreating the actual sample to obtain a solution to be detected of the actual sample;
(3) illumination: placing the two solutions to be detected under an ultraviolet light source for irradiation;
(4) raman measurement: setting working parameters of the laser Raman spectrometer: wavelength of laser, laser power and scanning time: respectively mixing the gold sol and the two photolyzed solutions to be detected according to the proportion of 10: 1 or 3: 2, and then detecting;
(5) and (3) characterization: scanning using a laser Raman spectrometer at 2230cm-1The Raman peak at (A) is taken as a qualitative characteristic peak.
2. The method according to claim 1, wherein the mass percent concentration of the potassium chloroaurate solution is 0.6-1%, the mass percent concentration of the trisodium citrate solution is 0.5-4.0%, and the volume ratio of the potassium chloroaurate solution to the trisodium citrate solution is 100: 3-12; the heating temperature is 100-150 ℃; stirring at a speed of 300-900 r/min; the heating time is 10-40 min.
3. The method according to claim 1 or 2, wherein the organic solvent is methanol or methanol water.
4. The method according to claim 1 or 2, wherein the actual sample is fruit or vegetable.
5. The method of claim 3, wherein the physical sample is fruit or vegetable.
6. The method according to claim 4, wherein 1-10 g of vegetable leaves or fruit skins are taken in the pretreatment process of the actual sample, the vegetable leaves or fruit skins are cut into pieces, an extracting agent is added, the vibration extraction is carried out for 10min, then the ultrasonic extraction is carried out for 3min, the extract is transferred to a volumetric flask, and the volume is fixed.
7. The method according to claim 5, wherein 1-10 g of vegetable leaves or fruit skins are taken in the pretreatment process of the actual sample, the vegetable leaves or fruit skins are cut into pieces, an extracting agent is added, the vibration extraction is carried out for 10min, then the ultrasonic extraction is carried out for 3min, the extract is transferred to a volumetric flask, and the volume is fixed.
8. The method according to claim 1, 2, 5, 6 or 7, wherein the wavelength of the ultraviolet light source in the step (3) is 302nm or 254nm, and the irradiation time is 10-60 min.
9. The method according to claim 1, 2, 5, 6 or 7, wherein the wavelength of the laser is set to 785nm, the laser power is set to 50-300 mW, and the scanning time is set to 5-30 s.
10. The method according to claim 8, wherein the wavelength of the laser is set to 785nm, the laser power is set to 50-300 mW, and the scanning time is set to 5-30 s.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106841163A (en) * | 2017-02-14 | 2017-06-13 | 山东出入境检验检疫局检验检疫技术中心 | The SERS method of quick detection fluorescent whitening agent FWA199 |
| CN106979942A (en) * | 2017-05-04 | 2017-07-25 | 华中师范大学 | A kind of Raman spectrum analysis method quantitative to synthesis in solid state compound combinatorial libraries individual and application thereof |
| CN108287152A (en) * | 2018-04-03 | 2018-07-17 | 江南大学 | A method of quickly detecting ethiprole using illumination and surface-enhanced Raman |
| US20200158646A1 (en) * | 2017-07-20 | 2020-05-21 | Phansco Co., Ltd. | Surface-enhanced raman scattering detection method for rapid detection of pesticide residues |
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- 2021-08-20 CN CN202110958744.4A patent/CN113552115A/en not_active Withdrawn
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106841163A (en) * | 2017-02-14 | 2017-06-13 | 山东出入境检验检疫局检验检疫技术中心 | The SERS method of quick detection fluorescent whitening agent FWA199 |
| CN106979942A (en) * | 2017-05-04 | 2017-07-25 | 华中师范大学 | A kind of Raman spectrum analysis method quantitative to synthesis in solid state compound combinatorial libraries individual and application thereof |
| US20200158646A1 (en) * | 2017-07-20 | 2020-05-21 | Phansco Co., Ltd. | Surface-enhanced raman scattering detection method for rapid detection of pesticide residues |
| CN108287152A (en) * | 2018-04-03 | 2018-07-17 | 江南大学 | A method of quickly detecting ethiprole using illumination and surface-enhanced Raman |
Non-Patent Citations (2)
| Title |
|---|
| SHUNA MI ET AL.: "Zero-Background Surface-Enhanced Raman Scattering Detection of Cymoxanil Based on the Change of the Cyano Group after Ultraviolet Irradiation", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, vol. 69, pages 520 - 527 * |
| 朱晴 等: "橘园土壤中嘧菌酯的残留消解动态分析", 湖南农业科学, no. 02, pages 40 - 42 * |
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