CN111111624A - Adsorbing material and method for detecting content of pyrethroid pesticide residues in tobacco leaves - Google Patents

Adsorbing material and method for detecting content of pyrethroid pesticide residues in tobacco leaves Download PDF

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CN111111624A
CN111111624A CN202010014174.9A CN202010014174A CN111111624A CN 111111624 A CN111111624 A CN 111111624A CN 202010014174 A CN202010014174 A CN 202010014174A CN 111111624 A CN111111624 A CN 111111624A
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pyrethroid
ring
monomer
adsorbing material
adsorbing
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CN111111624B (en
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李冉
宋旭艳
魏敏
潘曦
肜霖
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China Tobacco Hubei Industrial LLC
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    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
    • B01J20/26—Synthetic macromolecular compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D15/00—Separating processes involving the treatment of liquids with solid sorbents; Apparatus therefor
    • B01D15/08—Selective adsorption, e.g. chromatography
    • B01D15/10—Selective adsorption, e.g. chromatography characterised by constructional or operational features
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Abstract

The application discloses an adsorption material and a method for detecting the content of pyrethroid pesticide residues in tobacco leaves. The adsorption material is an oxime polymer which is flanked by aromatic conjugated rings, and the aromatic conjugated rings can generate pi-pi electron stacking effect with pyrethroid groups of pyrethroid substances, so that reliable adsorption force is formed. The adsorption material firstly adsorbs pyrethroid pesticide residues contained in the tobacco sample liquid, then carries out chromatographic analysis after desorption, and avoids the problems that the content of the pyrethroid pesticide residues is trace, so that the quantitative analysis cannot be carried out and the species cannot be qualitatively analyzed.

Description

Adsorbing material and method for detecting content of pyrethroid pesticide residues in tobacco leaves
Technical Field
The invention relates to the technical field of tobacco leaf pesticide residue detection, in particular to an adsorbing material and a method for detecting the content of pyrethroid pesticide residue in tobacco leaves.
Background
The development of agricultural industrialization, the production of agricultural products increasingly depends on chemical and biological products such as pesticides, antibiotics and hormones. The unreasonable use of the substances can lead to the overproof residue in agricultural products, influence the edible safety of consumers, and cause the consumers to have diseases and abnormal development in serious cases, even directly cause poisoning and death. The method controls the harm of pesticide residue to human body, one of the most effective methods is to strengthen the supervision of chemical and biological product use, and the capability level and efficiency of pesticide residue detection in food must be improved for ensuring the supervision. The pesticide residue detection in the world develops to multi-residue and rapid analysis, and the multi-residue detection is an important trend of pesticide residue analysis and has three advantages of 'multi', 'quick' and 'accurate'. From 2006 to 2008, the multi-residue detection standard for simultaneously determining more than 100 pesticides is formulated successively for agricultural products such as fruits, vegetables, grains, tea, fruit and vegetable juice, fruit wine, milk powder, edible fungi and the like.
Tobacco is used as a special economic crop, various types of pesticides are commonly used in order to effectively control plant diseases and insect pests in the production process, the phenomenon that pesticide residues exceed standards often occurs, the pesticide residues in tobacco leaves become an important factor influencing the safety of the tobacco leaves, 3 tobacco multiple pesticide residue detection industry standards are released in 2011 in the tobacco industry, and the series of standards can detect 146 pesticides by using 4 pretreatment methods and 3 analysis methods. The 73 pesticides with larger polarity are purified by QuEChERS and then analyzed by LC/MS/MS, the 38 pesticides with non-polarity or medium polarity are treated by the QuEChERS method and then purified by silica gel and Flori silica gel small columns, and analyzed by GC/MS and GC/ECD, and the 35 pesticides with organochlorine and pyrethroid are independently used as one class, and analyzed by GC/ECD after passing through a solid phase extraction small column. The industrial standards are used for analyzing a plurality of pesticides with wide application range in tobacco, such as 6 pesticides of metalaxyl, butralin, pendimethalin, flumetralin, lambda-cyhalothrin and dimethachlon (the above 3 standards do not contain dimethachlon), 4 pretreatment methods are also needed, the time and the labor are consumed, and the efficiency is low.
In order to shorten the analysis time and improve the detection efficiency, the Chinese tobacco general company releases an enterprise standard for detecting multiple pesticide residues in tobacco and tobacco products in 2014, and gas chromatography-tandem mass spectrometry and liquid chromatography-tandem mass spectrometry are used for detection, wherein 169 pesticides are detected by a gas-mass tandem method, and 141 pesticides are detected by a liquid-mass tandem method. In both methods, a QuEChERS method is adopted for sample pretreatment, and a tandem mass spectrometry method is adopted for analysis. Compared with the prior industry standard, the working efficiency can be greatly improved, and the labor burden is reduced.
However, the content of the pyrethroid pesticide residues in the tobacco leaves reaches a trace level basically. Chromatographic peaks are difficult to separate by adopting a chromatograph, the qualitative analysis effect is not ideal, and quantitative detection is more difficult.
Disclosure of Invention
In order to solve the problems, the application provides an adsorbing material and a method for detecting the content of pyrethroid pesticide residues in tobacco leaves, so that quantitative detection and qualitative analysis of specific types of the pyrethroid pesticide residues are realized.
The inventor unexpectedly finds that an imine chain formed by alternately forming a plurality of imine groups (-C = N-) through single bonds has a larger conjugated system, when an aromatic conjugated ring is connected to the imine chain, the aromatic conjugated ring can form pi-pi conjugation with the imine chain conjugated system, so that an electron delocalized orbit of the imine chain conjugated system is remarkably expanded, and the side-connected oxime polymer formed by the method has adsorbability on pyrethroid compounds. The structure determining the adsorbability is that the pyrethroid compound has a ph-O-ph group, the diphenyl ether group forms a p-pi conjugated system by a pi orbit of a benzene ring and a p orbit of lone pair electrons of an O atom, and the electron delocalization of the p-pi conjugated system is smaller than that of the pi-pi conjugated system. Whereas oxime polymers have large pi electrons capable of forming with the p electrons of the p-pi conjugated system at such longer distances, known as pi-p electron stacking, whereby molecular stacking occurs, resulting in a wider range of electron delocalization toward more stable states. Based on this, the invention of the present application has been completed.
Pyrethroid substance
Generally refers to compounds having the general structural formula,
Figure 100002_DEST_PATH_IMAGE002
. Some of the properties of pyrethroid pesticides are shown in the table below.
Figure 100002_DEST_PATH_IMAGE004
According to a first embodiment of the application, the adsorption material is used for adsorbing pyrethroid substances, and is an oxime polymer obtained by condensation polymerization of a monomer A with an amino group as a reactive group and a monomer B with an aldehyde group as a reactive group;
wherein monomer A has the structure shown in formula I:
Figure 100002_DEST_PATH_IMAGE006
；
monomer B has the structure shown in formula II:
Figure 100002_DEST_PATH_IMAGE008
；
in the formula I and the formula II,
Figure DEST_PATH_IMAGE010
represents an aromatic conjugated ring;
Figure DEST_PATH_IMAGE012
represents an aromatic conjugated ring; y, X is unsubstituted or substituted carboxyl or hydroxyl at any position, a and b are positive integers and are not simultaneously 1, and c and d are both positive integers.
Aromatic conjugated ring
Refers to a compound that conforms to the H ü ckel rule (Huckel rule), and refers to a compound when the pi electron number of the conjugated polyene (annulene) of a closed ring planar type is (4 n + 2), wherein n is 0 or a positive integer
Figure DEST_PATH_IMAGE014
、
Figure DEST_PATH_IMAGE016
The monocyclic ring of the five-membered or six-membered carbon heterocycle is preferably a monocyclic ring of an aromatic ring, a monocyclic ring of a five-membered or six-membered carbon heterocycle, and a condensed ring thereof, and specific examples of the monocyclic ring of the five-membered or six-membered carbon heterocycle include monocyclic rings such as a pyridine ring, a pyrimidine ring, a pyrrole ring, a furan ring, a thiophene ring, and imidazole, or condensed ring examples represented by purine, quinoline, naphthalene, and anthracene. It is understood that the aromatic conjugated ring of the present application may also be exemplified by a ring having negative or positive electricity, such as a dicyclopentadienyl ring, etc.
Regarding the number of the reactive groups in the monomer A and the monomer B, namely the values of a and B, when one of the two is 1, the obtained oxime polymer is a branched polymer; when both values are not 1, the resulting oxime polymer is a linear polymer or a bulk polymer. Branched polymers are preferred in this application, which gives the advantage of better solvent in organic solvents and lower viscosity, which sacrifices the size of the conjugated system of the imine chain.
In order to avoid the formation of a branched polymer, the oxime polymer of the present invention preferably has an average functionality of 2.2 to 3, preferably 2.4 to 2.8. Here, the average functionality is obtained from the reactive groups contained in the molecular structures of the monomers A and B and the reaction ratios of the two. Specifically, for example, if the number of reactive groups per molecule of monomer a is 3, the number of reactive groups per molecule of monomer B is 1, and the molar ratio of the reaction of monomer a and monomer B is 1.5:1, the average functionality = (1.8 × 3 +1 × 1)/(1.8 + 1) = 2.28.
The pendant group of the non-reactive group on the aromatic conjugated ring in the above-mentioned monomer A or monomer B is preferably a group having an active hydrogen, such as a carboxyl group or a hydroxyl group. The monomers A and B with the groups can form intermolecular hydrogen bonds with amino groups of the pyrethroid so as to improve the adsorption force on the pyrethroid.
There may be mentioned a relatively easily available example of the monomer A, the monomer B being melamine and the monomer B being 3, 5-dihydroxybenzaldehyde, 3, 4-dihydroxybenzaldehyde, 2-carboxybenzaldehyde or 3-carboxybenzaldehyde.
For the polycondensation reaction, the temperature of the polycondensation reaction can be 160-200 ℃, preferably 170-190 ℃, and particularly preferably 180 ℃; on the basis of the above, the time of the polycondensation reaction is 48 to 96 hours, preferably 60 to 84 hours, and particularly preferably 72 hours.
The solvent for the polycondensation reaction is an inert solvent, preferably DMSO or carbon tetrachloride.
As for the atmosphere of the reaction, it may be carried out in an inert atmosphere such as a nitrogen atmosphere, a helium atmosphere, a neon atmosphere or the like.
As for the manner of separating the reaction product from the reaction system, it can be adjusted according to the product characteristics. For reference, after the reaction is completed, the reaction mixture is washed with a mixture of DMF, methanol and THF in equal volume, dried at 60 deg.C and ground.
According to a second embodiment of the application, the application provides a method for detecting the content of pyrethroid pesticide residues in tobacco leaves by using the adsorbing material, which comprises the following steps:
(1) putting the adsorbing material into a tobacco leaf sample solution to obtain the adsorbing material adsorbing pyrethroid pesticide residues;
(2) desorbing the adsorbed pyrethroid pesticide residue into desorption liquid by using the adsorbing material to obtain sample injection liquid to be injected;
(3) and (4) enabling the sample injection liquid to pass through a chromatograph to obtain the pesticide residue content.
The stripping solution may be a solvent for pyrethroids, such as acetonitrile. As for the amount of the stripping solution, it is conceivable that the concentration of the pyrethroid type pesticide residue diluted can be within the detection accuracy of a chromatograph.
The desorption time is 10-30 min, preferably 12-20 min. The temperature of desorption may be room temperature.
The solvent of the sample solution is preferably a methanol-water solution, as a solvent for preferably dissolving the pesticide residue contained in the tobacco leaves to the maximum extent.
As regards the type of chromatograph and the chromatographic operating conditions, which are not the object of the present application, any chromatograph known in the art can carry out the present solution, for example HPLC-UV.
The adsorption material is an oxime polymer which is flanked by aromatic conjugated rings, and the aromatic conjugated rings can generate pi-pi electron stacking effect with pyrethroid groups of pyrethroid substances, so that reliable adsorption force is formed. The adsorption material firstly adsorbs pyrethroid pesticide residues contained in the tobacco sample liquid, then carries out chromatographic analysis after desorption, and avoids the problems that the content of the pyrethroid pesticide residues is trace, so that the quantitative analysis cannot be carried out and the species cannot be qualitatively analyzed.
Drawings
FIG. 1 is an infrared spectrum of the adsorbent synthesized in example 1.
Detailed Description
The following are specific examples of the present application and further describe the technical solutions of the present application, but the present application is not limited to these examples.
Example 1
And (4) synthesizing an adsorbing material. 0.126 g of melamine (molar mass 126.12), 0.245 g of 3, 5-dihydroxybenzaldehyde (molar mass 138.12) and DMSO (25 ml) were placed in a flask under a nitrogen atmosphere, and the mixture was refluxed at 180 ℃ for 72 hours, cooled, washed with a mixture of DMF (40 ml), methanol (40 ml) and THF (40 ml), dried at 60 ℃ and ground to obtain an adsorbent.
And (5) detecting pyrethroid pesticide residues. Weighing 0.3 g of tobacco leaves into a 4mL EP tube, adding 2mL of 45 vol% methanol-water solution, carrying out ultrasonic extraction for 5 min, taking 1mL of supernate, and diluting to 30 mL with 45% methanol-water solution for later use. The method comprises the steps of putting 30 mg of SNW material into 30 mL of sample solution (without adjusting pH), extracting for 50 min at the rotating speed of 600 rpm, removing the sample solution through centrifugal separation, adding 0.5 mL of acetonitrile, performing ultrasonic desorption for 15 min, performing centrifugal separation, and sampling 30 muL of sample to HPLC-UV analysis.
Example 2
And (4) synthesizing an adsorbing material. 0.252g of melamine (molar mass 126.12), 0.138 g of 3, 5-dihydroxybenzaldehyde (molar mass 138.12) and DMSO (25 ml) were placed in a flask under a nitrogen atmosphere, and the mixture was refluxed at 180 ℃ for 72 hours, cooled, washed with a mixture of DMF (40 ml), methanol (40 ml) and THF (40 ml), dried at 60 ℃ and ground to obtain an adsorbent. The pyrethroid pesticide residue was detected as in example 1.
Example 3
And (4) synthesizing an adsorbing material. 0.595g of 2,4, 6-triaminobenzene-1, 3, 5-tricarboxylic acid (molar mass 297.264), 0.138 g of 3, 4-dihydroxybenzaldehyde (molar mass 138.12) and carbon tetrachloride (25 ml) were added to a flask under a nitrogen atmosphere, and then the mixed solution was refluxed at 180 ℃ for 72 hours, cooled, washed with a mixed solution composed of DMF (40 ml), methanol (40 ml) and THF (40 ml), dried at 60 ℃ and ground to obtain an adsorbent. The pyrethroid pesticide residue was detected as in example 1.
Example 4
And (4) synthesizing an adsorbing material. 0.480g of 2, 4-diaminoquinazoline (molar mass 160.176), 0.138 g of 3, 4-dihydroxybenzaldehyde (molar mass 138.12) and carbon tetrachloride (25 ml) were added to a flask under a nitrogen atmosphere, and the mixture was refluxed at 180 ℃ for 72 hours, cooled, washed with a mixture of DMF (40 ml), methanol (40 ml) and THF (40 ml), dried at 60 ℃ and ground to obtain an adsorbent. The pyrethroid pesticide residue was detected as in example 1.
Example 5
And (4) synthesizing an adsorbing material. 0.246g of 2-aminopyrrole (molar mass 82.12), 0.138 g of 3, 4-dihydroxybenzaldehyde (molar mass 138.12) and carbon tetrachloride (25 ml) were added to the flask under a nitrogen atmosphere, and then the mixture was refluxed at 180 ℃ for 72 hours, cooled, washed with a mixture of DMF (40 ml), methanol (40 ml) and THF (40 ml), dried at 60 ℃ and ground to obtain an adsorbent. The pyrethroid pesticide residue was detected as in example 1.
Evaluation of
1. Infrared characterization
Examples of the invention1, carrying out an infrared test by a Fourier infrared spectrometer on the synthesized adsorbing material, the monomer melamine and the 3, 5-dihydroxy benzaldehyde, and obtaining an IR spectrum as shown in figure 1. As can be seen, the triazine ring is 1557 cm-1、1456cm-1The characteristic absorption peak proves that triazine environment is remained in the adsorbing material, and Ar-OH is 1200-1300 cm-1The stretching vibration peak still exists in SNWs, and-NH 2 is 3469cm-1And antisymmetric and symmetric telescopic vibration peak at 3419 cm-1, 1654 cm-1The bending vibration at (A) and the characteristic absorption band at-CHO at 2700-.
2. Adsorption Rate test
0.1g of the adsorbent synthesized in example was charged into 100ml of each adsorbent charged with C having a known concentration0Methiocarb
The concentration C of pyrethroid pesticide contained in the rest solution is detected by a chromatograph after the pyrethroid pesticide is placed in a 45vo% methanol-water solution prepared from six pyrethroid pesticides including isoprocarb, carbaryl, carbofuran, 3-hydroxy carbofuran, propoxur and methiocarb for 20min at room temperature1. Calculation of adsorption Rate = (C)0- C1）/ C0X 100%. The calculation results are shown in Table 2.
TABLE 2 test results of adsorption rates
Figure DEST_PATH_IMAGE018
3. Detection precision of residual agriculture detection in tobacco leaves
The performance of the adsorbing material synthesized in example 1 on the detection of the content of the residual agricultural crops in tobacco leaves is shown in table 3.
TABLE 3 test results for various pyrethroid pesticides
Figure DEST_PATH_IMAGE020
The specific embodiments described herein are merely illustrative of the spirit of the application. Various modifications or additions may be made to the described embodiments or alternatives may be employed by those skilled in the art without departing from the spirit or ambit of the present application as defined by the appended claims.

Claims (10)

1. An adsorption material is characterized in that the adsorption material is used for adsorbing pyrethroid substances, and oxime polymers are obtained by carrying out polycondensation on a monomer A taking an amino group as a reactive group and a monomer B taking an aldehyde group as a reactive group;
wherein monomer A has the structure shown in formula I:
Figure DEST_PATH_IMAGE002
；
monomer B has the structure shown in formula II:
Figure DEST_PATH_IMAGE004
；
in the formula I and the formula II,
Figure DEST_PATH_IMAGE006
represents an aromatic conjugated ring, preferably an aromatic ring monocyclic ring, a five-membered or six-membered carbon heterocyclic monocyclic ring and a condensed ring thereof;
Figure DEST_PATH_IMAGE008
represents an aromatic conjugated ring, preferably an aromatic ring monocyclic ring, a five-membered or six-membered carbon heterocyclic monocyclic ring and a condensed ring thereof; y, X is unsubstituted or substituted carboxyl or hydroxyl at any position, a and b are positive integers and are not simultaneously 1, and c and d are both positive integers.
2. The adsorbent material according to claim 1, wherein monomer a is melamine and monomer B is 3, 5-dihydroxybenzaldehyde, 3, 4-dihydroxybenzaldehyde, 2-carboxybenzaldehyde or 3-carboxybenzaldehyde.
3. The adsorption material of claim 1 or 2, wherein the oxime polymer has an average functionality of 2.2 to 3, preferably 2.4 to 2.8.
4. The adsorbing material according to any one of claims 1 to 3, wherein the oxime polymer is a branched polymer.
5. The adsorbing material according to any one of claims 1 to 4, wherein the temperature of the polycondensation reaction is 160 to 200 ℃, preferably 170 to 190 ℃, and the time of the polycondensation reaction is 48 to 96 hours, preferably 60 to 84 hours.
6. The adsorbing material according to any one of claims 1 to 5, wherein the solvent for the polycondensation reaction is an inert solvent, preferably DMSO or carbon tetrachloride.
7. A method for detecting the content of pyrethroid pesticide residues in tobacco leaves by using the adsorbing material as claimed in any one of claims 1 to 6 is characterized by comprising the following steps:
(1) putting the adsorbing material into a tobacco leaf sample solution to obtain the adsorbing material adsorbing pyrethroid pesticide residues;
(2) desorbing the adsorbed pyrethroid pesticide residue into desorption liquid by using the adsorbing material to obtain sample injection liquid to be injected;
(3) and (4) enabling the sample injection liquid to pass through a chromatograph to obtain the pesticide residue content.
8. The adsorbent material of claim 7, wherein the stripping solution is acetonitrile.
9. The adsorbent material according to claim 7, wherein the desorption time is 10 to 30min, preferably 12 to 20 min.
10. The adsorption material of claim 7, wherein the solvent of the tobacco sample fluid is a methanol-water solution.
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CN111889086A (en) * 2020-08-05 2020-11-06 西华师范大学 Fe3O4-NH2@ TpMA magnetic composite material and preparation method and application thereof
CN112525980A (en) * 2020-11-26 2021-03-19 厦门大学 Mass spectrum detection method for melamine in dairy products

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CN111889086A (en) * 2020-08-05 2020-11-06 西华师范大学 Fe3O4-NH2@ TpMA magnetic composite material and preparation method and application thereof
CN112525980A (en) * 2020-11-26 2021-03-19 厦门大学 Mass spectrum detection method for melamine in dairy products
CN112525980B (en) * 2020-11-26 2022-09-06 厦门大学 Mass spectrometry detection method for melamine in dairy products

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