CN108853865A - A method of degradation dinotefuran - Google Patents
A method of degradation dinotefuran Download PDFInfo
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- CN108853865A CN108853865A CN201811009647.5A CN201811009647A CN108853865A CN 108853865 A CN108853865 A CN 108853865A CN 201811009647 A CN201811009647 A CN 201811009647A CN 108853865 A CN108853865 A CN 108853865A
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- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D3/00—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances
- A62D3/02—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances by biological methods, i.e. processes using enzymes or microorganisms
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- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D2101/00—Harmful chemical substances made harmless, or less harmful, by effecting chemical change
- A62D2101/04—Pesticides, e.g. insecticides, herbicides, fungicides or nematocides
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Abstract
The present invention provides a kind of methods of dinotefuran of degrading, and described method includes following steps：(1) white-rot fungi is subjected to Liquid Culture；(2) by after Liquid Culture white-rot fungi and fluid nutrient medium mix with dinotefuran, 24~30 DEG C of standings.Method of the invention degrades to dinotefuran using white-rot fungi (YK-624), degradation efficiency reaches 31%, qualitative analysis has been carried out to the product of degradation, a kind of new compound is obtained, N- ((4aS, 7aS, E) -1- methyl hexahydro furyl [2,3-d] pyrimidine -2 (1H)-subunit) nitramide.
Description
Technical field
The present invention relates to microorganism fields, and in particular to a method of degradation dinotefuran.
Background technique
Dinotefuran (dinotefuran), chemical name are 1- methyl -2- nitro -3- (tetrahydro -3- furfuryl) guanidine, point
It is halogen-free in son with aromatic ring and using tetrahydrofuran base as substituent group, is the third generation nicotine researched and developed by Mitsui chemical company
Insecticides, with insecticidal spectrum is wide, interior suction osmosis is strong, insecticidal activity is high, the lasting period is long, to spies such as animals and plants safety height
Point, and resistance risk caused by one or two generation nicotinic insecticides can be overcome, it has a extensive future.The medicine was obtained in 2013 in China
Quasi- registration can be used for the pests such as paddy field prevention and treatment planthopper, rice smaller green leaf hopper.Currently, having existed about dinotefuran both at home and abroad
Agricultural product, paddy field, residue detection research in water body report.Although the toxicity of nicotinic insecticide is lower, with
Being widely used in agricultural production, the residual in surrounding medium are more and more paid attention to, exploitation degradation dinotefuran
Method can also seem ever more important.
Summary of the invention
The object of the present invention is to provide a kind of methods of dinotefuran of degrading.
To achieve the above object, the technical scheme is that：A method of degradation dinotefuran, the method includes with
Lower step：
(1) white-rot fungi (Phanerochaete sordida YK-624, hereinafter referred to as YK-624) is subjected to liquid training
It supports；
(2) by after Liquid Culture white-rot fungi and fluid nutrient medium mix with dinotefuran, 24~30 DEG C of standings.
The fluid nutrient medium of the Liquid Culture comprises the following components in parts by weight：9-11 parts of glucose, 0.2-0.3 portions of wine
Stone acid ammonium, 1.5-1.7 parts of anhydrous sodium acetates and 95-105 parts of Kirk salting liquids.
Wherein, the Kirk salting liquid includes following components in percentage by weight：1.8-2.2% potassium dihydrogen phosphate, 0.4-
0.6% bitter salt, 0.11-0.15% CALCIUM CHLORIDE DIHYDRATE, 0.0009-0.0011% thiamine hydrochloride, 1.5-1.8%
Kirk trace element solution.
The Kirk trace element solution includes following weight ratio ingredient：0.8-1%Nitrilotriacetate, 0.2-
0.4% bitter salt, 0.3-0.5% manganese sulfate monohydrate, 0.5-0.7% sodium chloride, seven hydrated sulfuric acid of 0.04-0.07% are sub-
Iron, 0.09-0.12% Cobalt monosulfate heptahydrate, 0.09-0.12% Zinc vitriol, 0.05-0.07% CALCIUM CHLORIDE DIHYDRATE,
0.005-0.007% Salzburg vitriol, 12 hydrazine aluminum sulfate potassium of 0.009-0.012%, 0.005-0.007% boric acid,
Bis- molybdic acid hydrate sodium of 0.006-0.008%.
Preferably, the fluid nutrient medium of the Liquid Culture comprises the following components in parts by weight：10 parts of glucose, 0.221
Part ammonium tartrate, 1.64 parts of anhydrous sodium acetates and 100 parts of Kirk salting liquids.
Preferably, the Kirk salting liquid includes following components in percentage by weight：2% potassium dihydrogen phosphate, 0.5% 7 water
Close magnesium sulfate, 0.13% CALCIUM CHLORIDE DIHYDRATE, 0.001% thiamine hydrochloride, 1.67%Kirk trace element solution.
The Kirk trace element solution includes following weight ratio ingredient：0.9%Nitrilotriacetate, 0.3% 7
Magnesium sulfate heptahydrate, 0.42% manganese sulfate monohydrate, 0.6% sodium chloride, 0.06% green vitriol, 0.11% 7 hydrated sulfuric acid
Cobalt, 0.11% Zinc vitriol, 0.06% CALCIUM CHLORIDE DIHYDRATE, 0.006% Salzburg vitriol, 0.011% 12 hydration
Aluminum aluminum sulfate, 0.006% boric acid, 0.007% 2 molybdic acid hydrate sodium.
Preferably, the white-rot fungi (YK-624), which carries out liquid cultivating method, is：It takes in potato agar glucose culture
The white-rot fungi mycelia piece activated on base (PDA) culture medium is seeded in the fluid nutrient medium, 24~30 DEG C of progress Liquid Cultures,
Wherein, the potato glucose agar medium includes following components：Potato 20%, glucose 2%, agar 2%.
Preferably, dwell temperature described in step (2) is 30 DEG C.
Preferably, the time cultivated in step (1) is 3~5 days.
Preferably, the temperature of Liquid Culture is 24-30 DEG C in step (1).
Preferably, the concentration of the dinotefuran in liquid medium is 0.05-0.15mmol/L.
Preferably, the time of standing described in step (2) is 20 days or more.
Inventor separates the fluid nutrient medium after degradation with white-rot fungi, and ethyl acetate is added into the liquid after separation
Extraction, obtains supernatant；Concentrated supernatant, and carry out gradient elution, preparative liquid chromatography with silica gel chromatography and further separate
Purifying, obtains a kind of compound of high-purity.
The compound is identified through mass spectrum, nuclear-magnetism, shown in structural formula such as formula (I)：
Molecular formula C7H12N4O3, molecular weight 200 is named as：N- ((4aS, 7aS, E) -1- methyl hexahydro furyl [2,3-d] pyrimidine -
2 (1H)-subunits) nitramide, English is named as：N-((4aS,7aS,E)-1-methylhexahydrofuro[2,3-d]
pyrimidin-2(1H)-ylidene)nitramide。
The present invention also provides a kind of methods of dinotefuran in degradation water, the described method comprises the following steps：
(1) white-rot fungi is subjected to Liquid Culture；
(2) by after Liquid Culture white-rot fungi and fluid nutrient medium be added in the water containing dinotefuran, mix, keep
24~30 DEG C of water temperature.
The fluid nutrient medium of the Liquid Culture comprises the following components in parts by weight：9-11 parts of glucose, 0.2-0.3 portions of wine
Stone acid ammonium, 1.5-1.7 parts of anhydrous sodium acetates and 95-105 parts of Kirk salting liquids.
The accumulation of dinotefuran in water environment can be prevented or be solved to the method, prevent pollution of the dinotefuran to water environment.
The beneficial effects of the present invention are：The present invention provides a kind of method of dinotefuran of degrading, the method for invention is utilized
White-rot fungi (YK-624) degrades to dinotefuran, and degradation efficiency reaches 31%, has carried out qualitative analysis to the product of degradation,
It is prepared for a kind of new compound, N- ((4aS, 7aS, E) -1- methyl hexahydro furyl [2,3-d] pyrimidine -2 (1H)-subunit) nitryl
Amine.The accumulation of dinotefuran in water environment can be prevented or be solved to the method for dinotefuran in the degradation water, prevent dinotefuran to water
The pollution of environment.
Detailed description of the invention
Fig. 1 is the structure of N- ((4aS, 7aS, E) -1- methyl hexahydro furyl [2,3-d] pyrimidine -2 (1H)-subunit) nitramide
Formula figure.
Fig. 2 is the mass spectrum of N- ((4aS, 7aS, E) -1- methyl hexahydro furyl [2,3-d] pyrimidine -2 (1H)-subunit) nitramide
Figure.
Fig. 3 is N- ((4aS, 7aS, E) -1- methyl hexahydro furyl [2,3-d] pyrimidine -2 (1H)-subunit) nitramide1H-
NMR(CD3OD) figure.
Fig. 4 is N- ((4aS, 7aS, E) -1- methyl hexahydro furyl [2,3-d] pyrimidine -2 (1H)-subunit) nitramide13C-
NMR(CD3OD) figure.
Fig. 5 is that N- ((4aS, 7aS, E) -1- methyl hexahydro furyl [2,3-d] pyrimidine -2 (1H)-subunit) nitramide inhibits people
The effect picture of marrow neuroblastoma cell line SH-SY5Y.
Specific embodiment
The present invention is specifically described below with reference to embodiment, but not limited to this.
Embodiment 1
1. experimental material
White-rot fungi YK-624 (Phanerochaete sordida YK-624) is used into potato glucose agar medium
(PDA, ingredient：Potato 20%, glucose 2%, agar 2%) passage expansion culture is carried out, it is saved backup in 4 DEG C of refrigerators.
2. a kind of embodiment of the method for degradation dinotefuran of the invention, the described method comprises the following steps：
(1) take at 30 DEG C of piece of white-rot fungi (YK-624) mycelia of the two panels diameter 10mm activated in PDA culture medium into
Row Liquid Culture；
(2) by after Liquid Culture white-rot fungi and fluid nutrient medium mix with dinotefuran, dinotefuran liquid medium within
In concentration be 0.1mmol/L, 30 DEG C stand 20 days.
The fluid nutrient medium of the Liquid Culture comprises the following components in parts by weight：10 parts of glucose, 0.221 part of tartaric acid
Ammonium, 1.64 parts of anhydrous sodium acetates and 100 parts of Kirk salting liquids.
The Kirk salting liquid includes following components in percentage by weight：2% potassium dihydrogen phosphate, 0.5% 7 hydrated sulfuric acid
Magnesium, 0.13% CALCIUM CHLORIDE DIHYDRATE, 0.001% thiamine hydrochloride, 1.67%Kirk trace element solution.
The Kirk trace element solution includes following weight ratio ingredient：0.9%Nitrilotriacetate, 0.3% 7
Magnesium sulfate heptahydrate, 0.42% manganese sulfate monohydrate, 0.6% sodium chloride, 0.06% green vitriol, 0.11% 7 hydrated sulfuric acid
Cobalt, 0.11% Zinc vitriol, 0.06% CALCIUM CHLORIDE DIHYDRATE, 0.006% Salzburg vitriol, 0.011% 12 hydration
Aluminum aluminum sulfate, 0.006% boric acid, 0.007% 2 molybdic acid hydrate sodium.
(3) after the completion of standing, liquid chromatography quantitative detection degradation results.
Internal standard compound is added into the culture solution after the completion of standing, and 20-30mL acetone is added, is smashed thallus with homogenizer
Matter is homogenized, and is rotated and is concentrated by evaporation after filtering, obtains sample solution.Sample solution enters high performance liquid chromatography (HPLC, chromatography
Column：5 μm of 4.6 × 250mm of Inertsil ODS-3) analysis.
The result shows that can degrade within white-rot fungi 20 days in Kirk culture medium 31% dinotefuran.
Embodiment 2
The qualitative analysis of catabolite.
(1) fluid nutrient medium after standing is separated with white-rot fungi, isometric acetic acid second is added into the liquid after separation
Ester extracts 3 times, merges supernatant；
(2) evaporation and concentration supernatant is chosen to install, and carries out gradient elution with silica gel chromatography, thin-layered chromatography carries out metabolism production
The tracking of object；
(3) the isolated product of silica gel chromatograph is further isolated and purified by preparative liquid chromatography.
The model of the chromatographic column of the preparation chromatography：Inertsil C30S-Select 5m 20x 250mm.
(4) it is analyzed by ESI-TOF-MS, mass spectrogram [M-H]-As shown in Fig. 2, [M-H]-=199.02 know compound
Molecular weight is 200.
(5) by spectral analysis of the nuclear magnetic resonance, in CD3Hydrogen spectrogram in OD as shown in figure 3, its in CD3Carbon spectrum in OD
Figure is as shown in Figure 4.Analysis to hydrogen spectrogram dynamic respond and the analysis to carbon spectrogram dynamic respond, the results are shown in Table 1.
Table 1
By to compound1H-NMR(CD3OD) spectrogram and13C-NMR(CD3OD) the analysis of spectrogram and mass spectrogram, confirmation system
The structural formula of standby obtained compound is as follows：
Molecular formula C7H12N4O3, molecular weight 200 is named as：N- ((4aS, 7aS, E) -1- methyl hexahydro furyl [2,3-d] pyrimidine -
2 (1H)-subunits) nitramide, English is named as：N-((4aS,7aS,E)-1-methylhexahydrofuro[2,3-d]
pyrimidin-2(1H)-ylidene)nitramide(PHPF)。
Embodiment 3
As one embodiment of the method for dinotefuran in a kind of degradation water of the invention, the method includes following steps
Suddenly：
(1) white-rot fungi is subjected to Liquid Culture；
(2) by after Liquid Culture white-rot fungi and fluid nutrient medium be added in the water containing dinotefuran, mix, keep
30 DEG C of water temperature.
The fluid nutrient medium of the Liquid Culture comprises the following components in parts by weight：10 parts of glucose, 0.221 part of tartaric acid
Ammonium, 1.64 parts of anhydrous sodium acetates and 100 parts of Kirk salting liquids.
The Kirk salting liquid includes following components in percentage by weight：2% potassium dihydrogen phosphate, 0.5% 7 hydrated sulfuric acid
Magnesium, 0.13% CALCIUM CHLORIDE DIHYDRATE, 0.001% thiamine hydrochloride, 1.67%Kirk trace element solution.
The Kirk trace element solution includes following weight ratio ingredient：0.9%Nitrilotriacetate, 0.3% 7
Magnesium sulfate heptahydrate, 0.42% manganese sulfate monohydrate, 0.6% sodium chloride, 0.06% green vitriol, 0.11% 7 hydrated sulfuric acid
Cobalt, 0.11% Zinc vitriol, 0.06% CALCIUM CHLORIDE DIHYDRATE, 0.006% Salzburg vitriol, 0.011% 12 hydration
Aluminum aluminum sulfate, 0.006% boric acid, 0.007% 2 molybdic acid hydrate sodium.
(3) degradation effect detects
Water sample before taking 20 days water samples of degradation reaction and degradation to start, is detected with liquid chromatography.The result shows that described
The 20 days time of method has reached 31% to the degradation efficiency of dinotefuran in water.
Finally, it should be noted that the above embodiments are merely illustrative of the technical solutions of the present invention rather than protects to the present invention
The limitation of range is protected, although the invention is described in detail with reference to the preferred embodiments, those skilled in the art should
Understand, it can be with modification or equivalent replacement of the technical solution of the present invention are made, without departing from the essence of technical solution of the present invention
And range.
Claims (8)
1. a kind of method for dinotefuran of degrading, which is characterized in that described method includes following steps：
(1) white-rot fungi is subjected to Liquid Culture；
(2) by after Liquid Culture white-rot fungi and fluid nutrient medium mix with dinotefuran, 24~30 DEG C of standings.
2. the method according to claim 1, wherein the fluid nutrient medium of the Liquid Culture includes following weight
The component of part：9-11 parts of glucose, 0.2-0.3 parts of ammonium tartrates, 1.5-1.7 parts of anhydrous sodium acetates and 95-105 portions of Kirk salt are molten
Liquid.
3. the method according to claim 1, wherein the fluid nutrient medium of the Liquid Culture includes following weight
The component of part：10 parts of glucose, 0.221 part of ammonium tartrate, 1.64 parts of anhydrous sodium acetates and 100 parts of Kirk salting liquids.
4. the method according to claim 1, wherein dwell temperature is 30 DEG C in the step (2).
5. the method according to claim 1, wherein the temperature of Liquid Culture is 24-30 in the step (1)
℃。
6. the method according to claim 1, wherein the time stood in the step (2) is 20 days or more.
7. a kind of method of dinotefuran in degradation water, which is characterized in that the described method comprises the following steps：
(1) white-rot fungi is subjected to Liquid Culture；
(2) by after Liquid Culture white-rot fungi and fluid nutrient medium be added in the water containing dinotefuran, mix, keep water temperature
24~30 DEG C.
8. the method according to the description of claim 7 is characterized in that the fluid nutrient medium of the Liquid Culture includes following weight
The component of part：9-11 parts of glucose, 0.2-0.3 parts of ammonium tartrates, 1.5-1.7 parts of anhydrous sodium acetates and 95-105 portions of Kirk salt are molten
Liquid.
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Cited By (5)
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| CN114540431A (en) * | 2022-02-18 | 2022-05-27 | 广州大学 | Method for biologically preparing 4, 4' -dihydroxy benzophenone by white rot fungi |
| CN114699705A (en) * | 2022-05-06 | 2022-07-05 | 广州大学 | Method for degrading imidaclothiz by adopting white rot fungi |
| CN114703071A (en) * | 2022-05-06 | 2022-07-05 | 广州大学 | Method for degrading imidacloprid by adopting white rot fungi |
| CN114703240A (en) * | 2022-05-06 | 2022-07-05 | 广州大学 | Method for biologically synthesizing 5-hydroxy imidacloprid and olefin imidacloprid |
| CN115944879A (en) * | 2023-01-16 | 2023-04-11 | 广州大学 | Method for degrading polycyclic aromatic hydrocarbon pyrene and benzo [ a ] pyrene by using white rot fungi |
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| CN114540431B (en) * | 2022-02-18 | 2023-08-04 | 广州大学 | Method for biologically preparing 4,4' -dihydroxybenzophenone by white rot fungi |
| CN114699705A (en) * | 2022-05-06 | 2022-07-05 | 广州大学 | Method for degrading imidaclothiz by adopting white rot fungi |
| CN114703071A (en) * | 2022-05-06 | 2022-07-05 | 广州大学 | Method for degrading imidacloprid by adopting white rot fungi |
| CN114703240A (en) * | 2022-05-06 | 2022-07-05 | 广州大学 | Method for biologically synthesizing 5-hydroxy imidacloprid and olefin imidacloprid |
| CN114699705B (en) * | 2022-05-06 | 2022-12-16 | 广州大学 | Method for degrading imidaclothiz by adopting white rot fungi |
| CN114703071B (en) * | 2022-05-06 | 2023-06-16 | 广州大学 | Method for degrading imidacloprid by using white rot fungi |
| CN114703240B (en) * | 2022-05-06 | 2023-10-13 | 广州大学 | Method for biosynthesis of 5-hydroxy imidacloprid and olefin imidacloprid |
| CN115944879A (en) * | 2023-01-16 | 2023-04-11 | 广州大学 | Method for degrading polycyclic aromatic hydrocarbon pyrene and benzo [ a ] pyrene by using white rot fungi |
| CN115944879B (en) * | 2023-01-16 | 2024-03-29 | 广州大学 | Method for degrading polycyclic aromatic hydrocarbon pyrene and benzo [ a ] pyrene by using white rot fungi |
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