CN101724112B - 二酰胺类杀虫剂分子印迹聚合物的制备方法及应用 - Google Patents
二酰胺类杀虫剂分子印迹聚合物的制备方法及应用 Download PDFInfo
- Publication number
- CN101724112B CN101724112B CN 200910227020 CN200910227020A CN101724112B CN 101724112 B CN101724112 B CN 101724112B CN 200910227020 CN200910227020 CN 200910227020 CN 200910227020 A CN200910227020 A CN 200910227020A CN 101724112 B CN101724112 B CN 101724112B
- Authority
- CN
- China
- Prior art keywords
- diamide insecticide
- imprinted polymer
- diamide
- insecticide
- molecular imprinted
- 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.)
- Active
Links
- 239000002917 insecticide Substances 0.000 title claims abstract description 68
- 229920000344 molecularly imprinted polymer Polymers 0.000 title claims abstract description 66
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 title claims abstract description 64
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 24
- 239000000178 monomer Substances 0.000 claims abstract description 21
- 239000003960 organic solvent Substances 0.000 claims abstract description 17
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 229920000642 polymer Polymers 0.000 claims abstract description 12
- 239000003999 initiator Substances 0.000 claims abstract description 11
- 230000007613 environmental effect Effects 0.000 claims abstract description 9
- 239000011259 mixed solution Substances 0.000 claims abstract description 8
- 150000007524 organic acids Chemical class 0.000 claims abstract description 6
- 230000000977 initiatory effect Effects 0.000 claims abstract description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 156
- 241000238631 Hexapoda Species 0.000 claims description 50
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 46
- 150000001408 amides Chemical class 0.000 claims description 43
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims description 30
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 27
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 27
- 239000000460 chlorine Substances 0.000 claims description 27
- 229910052801 chlorine Inorganic materials 0.000 claims description 27
- 239000003795 chemical substances by application Substances 0.000 claims description 25
- 239000005901 Flubendiamide Substances 0.000 claims description 24
- ZGNITFSDLCMLGI-UHFFFAOYSA-N flubendiamide Chemical group CC1=CC(C(F)(C(F)(F)F)C(F)(F)F)=CC=C1NC(=O)C1=CC=CC(I)=C1C(=O)NC(C)(C)CS(C)(=O)=O ZGNITFSDLCMLGI-UHFFFAOYSA-N 0.000 claims description 24
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims description 23
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 8
- 238000002414 normal-phase solid-phase extraction Methods 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 7
- 239000002689 soil Substances 0.000 claims description 7
- 239000000243 solution Substances 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 238000001291 vacuum drying Methods 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical group OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 5
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 claims description 5
- 238000011010 flushing procedure Methods 0.000 claims description 5
- 239000007791 liquid phase Substances 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- ZESXUEKAXSBANL-UHFFFAOYSA-N trifluoromethyl prop-2-enoate Chemical compound FC(F)(F)OC(=O)C=C ZESXUEKAXSBANL-UHFFFAOYSA-N 0.000 claims description 5
- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 claims description 4
- XLBGQPBFCCCZNH-QHGLUPRGSA-N CCC(=O)N[C@@H](C)C(C1=CC=CC=C1)O Chemical compound CCC(=O)N[C@@H](C)C(C1=CC=CC=C1)O XLBGQPBFCCCZNH-QHGLUPRGSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 4
- LOWXRSDGZBWVKH-UHFFFAOYSA-N benzoic acid prop-2-enamide Chemical compound NC(=O)C=C.OC(=O)C1=CC=CC=C1 LOWXRSDGZBWVKH-UHFFFAOYSA-N 0.000 claims description 4
- 229950005499 carbon tetrachloride Drugs 0.000 claims description 4
- ZZKAIKCETMSCBY-UHFFFAOYSA-N formic acid;styrene Chemical compound OC=O.C=CC1=CC=CC=C1 ZZKAIKCETMSCBY-UHFFFAOYSA-N 0.000 claims description 4
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 4
- 229910052753 mercury Inorganic materials 0.000 claims description 4
- 238000000746 purification Methods 0.000 claims description 4
- 230000005855 radiation Effects 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 claims description 3
- -1 4-vinylpridine Chemical compound 0.000 claims description 3
- 239000000945 filler Substances 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- GZBSIABKXVPBFY-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)CO GZBSIABKXVPBFY-UHFFFAOYSA-N 0.000 claims description 2
- DULCUDSUACXJJC-UHFFFAOYSA-N Ethyl phenylacetate Chemical compound CCOC(=O)CC1=CC=CC=C1 DULCUDSUACXJJC-UHFFFAOYSA-N 0.000 claims description 2
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical group CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 claims description 2
- XZKRXPZXQLARHH-UHFFFAOYSA-N buta-1,3-dienylbenzene Chemical compound C=CC=CC1=CC=CC=C1 XZKRXPZXQLARHH-UHFFFAOYSA-N 0.000 claims description 2
- 238000004587 chromatography analysis Methods 0.000 claims description 2
- 230000001186 cumulative effect Effects 0.000 claims description 2
- 238000010828 elution Methods 0.000 claims description 2
- 230000002452 interceptive effect Effects 0.000 claims description 2
- 125000000864 peroxy group Chemical group O(O*)* 0.000 claims description 2
- VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical compound NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 claims description 2
- 238000001514 detection method Methods 0.000 abstract description 9
- 238000000034 method Methods 0.000 abstract description 9
- 238000001035 drying Methods 0.000 abstract description 5
- 238000004140 cleaning Methods 0.000 abstract description 3
- 238000005406 washing Methods 0.000 abstract description 2
- 239000012472 biological sample Substances 0.000 abstract 1
- 239000003431 cross linking reagent Substances 0.000 abstract 1
- 238000000227 grinding Methods 0.000 abstract 1
- 238000002156 mixing Methods 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 239000011148 porous material Substances 0.000 abstract 1
- 238000012216 screening Methods 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 47
- 229960000583 acetic acid Drugs 0.000 description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 25
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 25
- 239000012362 glacial acetic acid Substances 0.000 description 21
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 102100023487 Lens fiber major intrinsic protein Human genes 0.000 description 9
- 239000000523 sample Substances 0.000 description 9
- 239000002245 particle Substances 0.000 description 8
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 7
- 235000019253 formic acid Nutrition 0.000 description 7
- 230000014759 maintenance of location Effects 0.000 description 7
- 238000005303 weighing Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 238000011084 recovery Methods 0.000 description 6
- 235000013311 vegetables Nutrition 0.000 description 6
- 239000003905 agrochemical Substances 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 239000011324 bead Substances 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 150000002527 isonitriles Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000447 pesticide residue Substances 0.000 description 4
- 238000004506 ultrasonic cleaning Methods 0.000 description 4
- 230000000274 adsorptive effect Effects 0.000 description 3
- 239000012496 blank sample Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- ZXLYUNPVVODNRE-UHFFFAOYSA-N 6-ethenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=C)=N1 ZXLYUNPVVODNRE-UHFFFAOYSA-N 0.000 description 2
- 101710085496 C-X-C motif chemokine 2 Proteins 0.000 description 2
- 241000426497 Chilo suppressalis Species 0.000 description 2
- 241000098289 Cnaphalocrocis medinalis Species 0.000 description 2
- 241000008892 Cnaphalocrocis patnalis Species 0.000 description 2
- 101710087757 Lens fiber major intrinsic protein Proteins 0.000 description 2
- 241001253920 Ryania Species 0.000 description 2
- 241001249129 Scirpophaga incertulas Species 0.000 description 2
- 102100038138 WD repeat-containing protein 26 Human genes 0.000 description 2
- XBJFCYDKBDVADW-UHFFFAOYSA-N acetonitrile;formic acid Chemical compound CC#N.OC=O XBJFCYDKBDVADW-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000004454 trace mineral analysis Methods 0.000 description 2
- 101100457315 Arabidopsis thaliana MIP3 gene Proteins 0.000 description 1
- 235000006008 Brassica napus var napus Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- 102100023703 C-C motif chemokine 15 Human genes 0.000 description 1
- 102100023701 C-C motif chemokine 18 Human genes 0.000 description 1
- 102100036850 C-C motif chemokine 23 Human genes 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- 241001674939 Caulanthus Species 0.000 description 1
- 239000005886 Chlorantraniliprole Substances 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- 241000254171 Curculionidae Species 0.000 description 1
- 239000005889 Cyantraniliprole Substances 0.000 description 1
- 102100023760 Cytosolic iron-sulfur assembly component 2B Human genes 0.000 description 1
- 241001517923 Douglasiidae Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 241000258937 Hemiptera Species 0.000 description 1
- 101100382875 Homo sapiens CCL15 gene Proteins 0.000 description 1
- 101100382881 Homo sapiens CCL18 gene Proteins 0.000 description 1
- 101100005560 Homo sapiens CCL23 gene Proteins 0.000 description 1
- 101000906803 Homo sapiens Cytosolic iron-sulfur assembly component 2B Proteins 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- 241000594036 Liriomyza Species 0.000 description 1
- 101100457309 Magnaporthe oryzae (strain 70-15 / ATCC MYA-4617 / FGSC 8958) MIP11 gene Proteins 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000209094 Oryza Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 101150006573 PAN1 gene Proteins 0.000 description 1
- 241000500437 Plutella xylostella Species 0.000 description 1
- 101100457316 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) MIP6 gene Proteins 0.000 description 1
- 241000256247 Spodoptera exigua Species 0.000 description 1
- 241000985245 Spodoptera litura Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- PSOVNZZNOMJUBI-UHFFFAOYSA-N chlorantraniliprole Chemical compound CNC(=O)C1=CC(Cl)=CC(C)=C1NC(=O)C1=CC(Br)=NN1C1=NC=CC=C1Cl PSOVNZZNOMJUBI-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- DVBUIBGJRQBEDP-UHFFFAOYSA-N cyantraniliprole Chemical compound CNC(=O)C1=CC(C#N)=CC(C)=C1NC(=O)C1=CC(Br)=NN1C1=NC=CC=C1Cl DVBUIBGJRQBEDP-UHFFFAOYSA-N 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 108010069583 lens intrinsic protein MIP 21 Proteins 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 238000000899 pressurised-fluid extraction Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000002470 solid-phase micro-extraction Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000000194 supercritical-fluid extraction Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
实施例 | 氟虫酰胺分子印迹聚合物 | 模板分子 | 聚合单体 | 交联剂 | 致孔剂 | 引发剂 | 冲洗用有机溶剂 | 有机酸 |
实施例2 | MIP2 | 氟虫酰胺0.1450g | AM0.0721g | TRIM0.0727g | 二氯甲烷10mL | 偶氮二异丁腈0.2134g | ①甲醇+乙酸;②甲醇 | 冰醋酸 |
实施例3 | MIP3 | 氟虫酰胺0.2351g | TFMAA0.2354 | N,N-二甲基二丙烯酰胺2.2130g | 氯仿15mL | 偶氮二异丁腈0.3125g | ①乙腈+甲酸;②甲醇 | 甲酸 |
实施例4 | MIP4 | 氟虫酰胺0.0719g | MMA0.1411g | N,N,-1,4-亚苯基二丙烯酰胺0.5403g | 乙腈10mL | 偶氮二异丁腈0.2031g | ①氯仿+乙酸;②甲醇 | 冰醋酸 |
实施例5 | MIP5 | 氟虫酰胺0.0540g | DEAEM0.2581g | 3,5-二(丙烯酰胺)苯甲酸1.0160g | 甲醇10mL | 偶氮二异丁腈0.3029g | ①甲醇+乙酸;②甲醇 | 冰醋酸 |
实施例6 | MIP6 | 氟虫酰胺0.0552g | AP 0.2503gAM 0.2511g | DVB5.301g | 异丙醇5mL | 偶氮二异丁腈0.3102g | ①甲醇+乙酸;②甲醇 | 冰醋酸 |
实施例7 | MIP7 | 氟虫酰胺0.0561g | 4-VP0.3107g,DAMPS0.3019g | N,O-二丙酰-L-苯丙氨醇6.031g | 四氯甲烷10mL | 偶氮二异丁腈0.3145g | ①甲醇+乙酸;②甲醇 | 冰醋酸 |
实施例8 | MIP8 | 氟虫酰胺0.0286g | 2-VP0.1541g,AM0.1545g | PETRA6.0108g | 氯仿10mL | 偶氮二异丁腈0.4813g | ①甲醇+乙酸;②甲醇 | 冰醋酸 |
实施例9 | MIP9 | 氟虫酰胺0.0357g | 对乙烯苯甲酸0.3013g | PETEA6.131g | 氯仿10mL | 偶氮二异丁腈0.3001g | ①甲醇+乙酸;②甲醇 | 冰醋酸 |
实施例10 | MIP10 | 氟虫酰胺0.0401g | ITA0.6011g | EGDMA0.6100g | 氯仿15mL | 偶氮二异丁腈0.4071g | ①甲醇+乙酸;②甲醇 | 冰醋酸 |
实施例11 | MIP11 | 氟虫酰胺0.0502g | 1-乙烯基咪唑0.1231g,丙烯酸0.3007g | EGDMA0.5130g | 氯仿19mL | 偶氮二异丁腈0.6012g | ①甲醇+乙酸;②甲醇 | 冰醋酸 |
实施例12 | MIP12 | 氟虫酰胺0.4704g | NVP0.4711g | EGDMA0.4703g | 氯仿18mL | 偶氮二异丁腈0.8107g | ①甲醇+乙酸;②甲醇 | 冰醋酸 |
实施例13 | MIP13 | 氟虫酰胺0.6118g | DTA1.2309g | EGDMA2.4507g | 氯仿8mL | 偶氮二异丁腈1.3231g | ①乙腈+甲酸;②乙腈 | 甲酸 |
实施例 | 氯虫酰胺分子印迹聚合物 | 模板分子 | 聚合单体 | 交联剂 | 致孔剂 | 引发剂 | 冲洗用有机溶剂 | 有机酸 |
实施例15 | MIP15 | 氯虫酰胺0.1551g | AM0.0802g | TRIM0.0810g | 二氯甲烷10mL | 偶氮二异丁腈0.2234g | ①甲醇+乙酸;②甲醇 | 冰醋酸 |
实施例16 | MIP16 | 氯虫酰胺0.2359g | TFMAA0.2360g | N,N-二甲基二丙烯酰胺2.2211g | 氯仿15mL | 偶氮二异丁腈0.3005g | ①乙腈+甲酸;②甲醇 | 甲酸 |
实施例17 | MIP17 | 氯虫酰胺0.0720g | MMA0.1500g | N,N,-1,4-亚苯基二丙烯酰胺0.5003g | 乙腈10mL | 偶氮二异丁腈0.2133g | ①氯仿+乙酸;②甲醇 | 冰醋酸 |
实施例18 | MIP18 | 氯虫酰胺0.0573g | DEAEM0.2603g | 3,5-二(丙烯酰胺)苯甲酸1.1114g | 甲醇10mL | 偶氮二异丁腈0.3120g | ①甲醇+乙酸;②甲醇 | 冰醋酸 |
实施例19 | MIP19 | 氯虫酰胺0.0557g | AP 0.2503gAM 0.2509g | DVB5.4131g | 异丙醇8mL | 偶氮二异丁腈0.3212g | ①甲醇+乙酸;②甲醇 | 冰醋酸 |
实施例20 | MIP20 | 氯虫酰胺0.0496g | 4-VP0.3118g,DAMPS0.2919g | N,O-二丙酰-L-苯丙氨醇5.9317g | 四氯甲烷10mL | 偶氮二异丁腈0.3176g | ①甲醇+乙酸;②甲醇 | 冰醋酸 |
实施例21 | MIP21 | 氯虫酰胺0.0307g | 2-VP0.1501g,AM0.1540g | PETRA6.1128g | 氯仿10mL | 偶氮二异丁腈0.4517g | ①甲醇+乙酸;②甲醇 | 冰醋酸 |
实施例22 | MIP22 | 氯虫酰胺0.0457g | 对乙烯苯甲酸0.4017g | PETEA6.0316g | 氯仿10mL | 偶氮二异丁腈0.3001g | ①甲醇+乙酸;②甲醇 | 冰醋酸 |
实施例23 | MIP23 | 氯虫酰胺0.0423g | ITA0.7100g | EGDMA0.7201g | 氯仿15mL | 偶氮二异丁腈0.4185g | ①甲醇+乙酸;②甲醇 | 冰醋酸 |
实施例24 | MIP24 | 氯虫酰胺0.0512g | 1-乙烯基咪唑0.1403g,丙烯酸0.3105g | EGDMA0.5333g | 氯仿19mL | 偶氮二异丁腈0.5812g | ①甲醇+乙酸;②甲醇 | 冰醋酸 |
实施例25 | MIP25 | 氯虫酰胺0.4533g | NVP0.4530g | EGDMA0.4517g | 氯仿18mL | 偶氮二异丁腈0.9001g | ①甲醇+乙酸;②甲醇 | 冰醋酸 |
实施例26 | MIP26 | 氯虫酰胺0.6208g | DTA1.2549g | EGDMA2.5515g | 氯仿12mL | 偶氮二异丁腈1.5235g | ①乙腈+甲酸;②乙腈 | 甲酸 |
MI代号 | 单体 | 交联剂 | 模板分子 | 聚合物平均粒径(μm) | 模板分子通过MIP柱与对照柱的保留时间比 |
MIP1 | MAA | EGDMA | 氟虫酰胺 | 56 | 3.2 |
MIP14 | MAA | EGDMA | 氯虫酰胺 | 56 | 4.1 |
MIP27 | MAA | EGDMA | 氰虫酰胺 | 56 | 3.8 |
MIP28 | MAADAMPS | EGDMA | 氯虫酰胺+氰虫酰胺 | 56 | 4.5(氯虫酰胺)3.7(氰虫酰胺) |
Claims (3)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 200910227020 CN101724112B (zh) | 2009-11-25 | 2009-11-25 | 二酰胺类杀虫剂分子印迹聚合物的制备方法及应用 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 200910227020 CN101724112B (zh) | 2009-11-25 | 2009-11-25 | 二酰胺类杀虫剂分子印迹聚合物的制备方法及应用 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN101724112A CN101724112A (zh) | 2010-06-09 |
CN101724112B true CN101724112B (zh) | 2011-06-15 |
Family
ID=42445720
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN 200910227020 Active CN101724112B (zh) | 2009-11-25 | 2009-11-25 | 二酰胺类杀虫剂分子印迹聚合物的制备方法及应用 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN101724112B (zh) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102212167A (zh) * | 2011-02-18 | 2011-10-12 | 刘庆山 | 一种碱性成纤维生长因子分子印迹聚合物及其制备方法和应用 |
CN103842390B (zh) * | 2011-11-02 | 2015-12-09 | 英派尔科技开发有限公司 | 印迹光子聚合物及其制备方法和应用 |
CN103127920B (zh) * | 2011-12-01 | 2015-03-25 | 司法部司法鉴定科学技术研究所 | 唑吡坦分子印迹固相萃取小柱 |
CN103940932A (zh) * | 2013-01-17 | 2014-07-23 | 中国农业科学院兰州畜牧与兽药研究所 | 一种非生物学筛选抗病毒中药有效成分的方法 |
CN103936923A (zh) * | 2013-01-22 | 2014-07-23 | 刘庆山 | 一种胡黄连苷ⅱ表面印迹新材料的制备方法和应用 |
CN103772595B (zh) * | 2014-01-16 | 2016-01-20 | 昆明理工大学 | 一种多模板分子印迹整体棒的制备方法 |
CN104888740B (zh) * | 2015-06-11 | 2017-04-26 | 大理州质量技术监督综合检测中心 | 一种乌洛托品分子印迹固相萃取柱的制备方法及应用 |
US11351520B2 (en) | 2019-11-11 | 2022-06-07 | King Fahd University Of Petroleum And Minerals | Crosslinked resin, synthesis thereof, and use for removing organic dyes |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1718593A (zh) * | 2004-07-06 | 2006-01-11 | 中国科学院化学研究所 | 一种分子印迹聚合物的制备方法 |
CN1800246A (zh) * | 2005-01-05 | 2006-07-12 | 中国科学院大连化学物理研究所 | 一种苯脲类除草剂的分子印迹聚合物的制备方法 |
-
2009
- 2009-11-25 CN CN 200910227020 patent/CN101724112B/zh active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1718593A (zh) * | 2004-07-06 | 2006-01-11 | 中国科学院化学研究所 | 一种分子印迹聚合物的制备方法 |
CN1800246A (zh) * | 2005-01-05 | 2006-07-12 | 中国科学院大连化学物理研究所 | 一种苯脲类除草剂的分子印迹聚合物的制备方法 |
Also Published As
Publication number | Publication date |
---|---|
CN101724112A (zh) | 2010-06-09 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN101724112B (zh) | 二酰胺类杀虫剂分子印迹聚合物的制备方法及应用 | |
He et al. | Novel restricted access materials combined to molecularly imprinted polymers for selective solid-phase extraction of organophosphorus pesticides from honey | |
Zhou et al. | Preparation, evaluation and application of molecularly imprinted solid-phase microextraction monolith for selective extraction of pirimicarb in tomato and pear | |
CN102532390B (zh) | 三嗪类除草剂及其代谢物分子印迹聚合物微球、其制备方法及应用 | |
CN101721981B (zh) | 一种分子印迹聚合物及其制备方法与应用 | |
Bakas et al. | Molecularly imprinted polymer cartridges coupled to high performance liquid chromatography (HPLC-UV) for simple and rapid analysis of fenthion in olive oil | |
CN106317325B (zh) | 三唑类农药分子印迹聚合物微球,固相萃取柱及其应用 | |
Martins et al. | Design and development of molecularly imprinted polymers for the selective extraction of deltamethrin in olive oil: An integrated computational-assisted approach | |
Hu et al. | Development of sample preparation method for auxin analysis in plants by vacuum microwave-assisted extraction combined with molecularly imprinted clean-up procedure | |
Pei et al. | Graphene reinforced multiple monolithic fiber solid-phase microextraction of phenoxyacetic acid herbicides in complex samples | |
Liu et al. | Novel method for the determination of five carbamate pesticides in water samples by dispersive liquid–liquid microextraction combined with high performance liquid chromatography | |
Boulanouar et al. | Synthesis and application of molecularly imprinted polymers for the selective extraction of organophosphorus pesticides from vegetable oils | |
Yan et al. | Ionic liquid-mediated molecularly imprinted solid-phase extraction coupled with gas chromatography-electron capture detector for rapid screening of dicofol in vegetables | |
CN104502504B (zh) | 一种蔬菜和水果中氯虫苯甲酰胺残留量的测定方法 | |
CN102875730B (zh) | 拟除虫菊酯片段印迹聚合物制备方法 | |
Öter et al. | Molecularly imprinted polymer synthesis and selective solid phase extraction applications for the detection of ziram, a dithiocarbamate fungicide | |
CN102174148A (zh) | 三嗪类除草剂分子印迹固相萃取材料的制备 | |
CN101565483B (zh) | 苄嘧磺隆分子印迹聚合物的制备方法及其应用 | |
CN102371084A (zh) | 一种邻苯二甲酸二丁酯分子印迹固相萃取小柱及其制备方法和应用 | |
Liu et al. | Uniform-sized molecularly imprinted polymer for metsulfuron-methyl by one-step swelling and polymerization method | |
CN104502507A (zh) | 一种氯虫苯甲酰胺残留量的gc-nci-ms测定方法 | |
Qi et al. | Molecularly imprinted solid‐phase extraction coupled with HPLC for the selective determination of monobutyl phthalate in bottled water | |
Svoboda et al. | Synthesis of a molecularly imprinted sorbent for selective solid-phase extraction of β-N-methylamino-l-alanine | |
CN109298111A (zh) | 果蔬中多种农残同时检测的方法 | |
Guo et al. | Molecularly imprinted solid-phase extraction for the selective determination of valnemulin in feeds with high performance liquid chromatography |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20180222 Address after: 410014 Changsha Avenue 550 comprehensive building, Changsha City, Hunan Province, 101 Patentee after: Hunan addition Testing Co.,Ltd. Address before: 410007 Changsha Furong Road, Hunan, No. two, No. 251 Patentee before: HUNAN Research Institute OF CHEMICAL INDUSTRY |
|
CP01 | Change in the name or title of a patent holder | ||
CP01 | Change in the name or title of a patent holder |
Address after: 410014 101, complex building, No. 550, Changsha Avenue, Yuhua District, Changsha City, Hunan Province Patentee after: Hunan Chemical Research Institute Testing Technology Co.,Ltd. Address before: 410014 101, complex building, No. 550, Changsha Avenue, Yuhua District, Changsha City, Hunan Province Patentee before: Hunan addition Testing Co.,Ltd. |
|
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20240110 Address after: No. 251, Section 2, Furong Middle Road, Changsha City, Hunan Province, 410000 Patentee after: HUNAN RESEARCH INSTITUTE OF CHEMICAL INDUSTRY Co.,Ltd. Address before: 410014 101, complex building, No. 550, Changsha Avenue, Yuhua District, Changsha City, Hunan Province Patentee before: Hunan Chemical Research Institute Testing Technology Co.,Ltd. |