CN109762015A - A kind of avermectin B2a phosphorylation modification object and its preparation method and application - Google Patents
A kind of avermectin B2a phosphorylation modification object and its preparation method and application Download PDFInfo
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- CN109762015A CN109762015A CN201910141972.5A CN201910141972A CN109762015A CN 109762015 A CN109762015 A CN 109762015A CN 201910141972 A CN201910141972 A CN 201910141972A CN 109762015 A CN109762015 A CN 109762015A
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- CWGATOJEFAKFBK-UHFFFAOYSA-N Ac-(E)-8-Tridecen-1-ol Natural products C1C(O)C(C)C(C(C)CC)OC11OC(CC=C(C)C(OC2OC(C)C(OC3OC(C)C(O)C(OC)C3)C(OC)C2)C(C)C=CC=C2C3(C(C(=O)O4)C=C(C)C(O)C3OC2)O)CC4C1 CWGATOJEFAKFBK-UHFFFAOYSA-N 0.000 title claims abstract description 89
- SHURRSUZDBDBMX-JLSLGBNPSA-N avermectin B2a Natural products CC[C@H](C)[C@H]1O[C@@]2(C[C@@H]3C[C@@H](CC=C(/C)[C@@H](O[C@H]4C[C@H](OC)[C@@H](O[C@H]5C[C@H](OC)[C@@H](O)[C@H](C)O5)[C@H](C)O4)[C@@H](C)C=CC=C6/OC[C@@H]7[C@H](O)C(=C[C@@H](C(=O)O3)[C@]67O)C)O2)C[C@@H](O)[C@@H]1C SHURRSUZDBDBMX-JLSLGBNPSA-N 0.000 title claims abstract description 88
- CWGATOJEFAKFBK-PDVFGPFMSA-N 5-o-demethyl-22,23-dihydro-23-hydroxy-(13r,23s)-avermectin a1a Chemical compound C1[C@H](O)[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 CWGATOJEFAKFBK-PDVFGPFMSA-N 0.000 title claims abstract description 87
- 230000026731 phosphorylation Effects 0.000 title claims abstract description 60
- 238000006366 phosphorylation reaction Methods 0.000 title claims abstract description 60
- 230000004048 modification Effects 0.000 title claims abstract description 55
- 238000012986 modification Methods 0.000 title claims abstract description 55
- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- 241000219109 Citrullus Species 0.000 claims abstract description 40
- 235000012828 Citrullus lanatus var citroides Nutrition 0.000 claims abstract description 40
- 238000010894 electron beam technology Methods 0.000 claims abstract description 21
- 229910019142 PO4 Inorganic materials 0.000 claims abstract description 14
- 239000010452 phosphate Substances 0.000 claims abstract description 14
- 241000243785 Meloidogyne javanica Species 0.000 claims abstract description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims abstract description 8
- 239000003814 drug Substances 0.000 claims abstract description 6
- 229940079593 drug Drugs 0.000 claims abstract description 6
- 230000002265 prevention Effects 0.000 claims abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 46
- 239000000243 solution Substances 0.000 claims description 32
- 235000019441 ethanol Nutrition 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 230000001376 precipitating effect Effects 0.000 claims description 14
- 239000001488 sodium phosphate Substances 0.000 claims description 13
- 229910000162 sodium phosphate Inorganic materials 0.000 claims description 13
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical group [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 claims description 13
- 239000005660 Abamectin Substances 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- RRZXIRBKKLTSOM-XPNPUAGNSA-N avermectin B1a Chemical compound C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 RRZXIRBKKLTSOM-XPNPUAGNSA-N 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- 239000011259 mixed solution Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 229910001413 alkali metal ion Chemical group 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical group [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 4
- 239000001257 hydrogen Substances 0.000 abstract description 4
- 239000003905 agrochemical Substances 0.000 abstract description 2
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 241000196324 Embryophyta Species 0.000 description 10
- 238000011835 investigation Methods 0.000 description 8
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- 238000004090 dissolution Methods 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- -1 phosphate radical Chemical class 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000001291 vacuum drying Methods 0.000 description 6
- 241000238631 Hexapoda Species 0.000 description 5
- 241000219112 Cucumis Species 0.000 description 4
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 4
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000003306 harvesting Methods 0.000 description 3
- 239000003607 modifier Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- IBSREHMXUMOFBB-JFUDTMANSA-N 5u8924t11h Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O3)C=C[C@H](C)[C@@H](C(C)C)O4)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 IBSREHMXUMOFBB-JFUDTMANSA-N 0.000 description 2
- 241000244206 Nematoda Species 0.000 description 2
- 230000000857 drug effect Effects 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 206010067482 No adverse event Diseases 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- ZPAKHHSWIYDSBJ-QDXJZMFISA-N avermectin b2 Chemical compound O1C(C)C(O)C(OC)CC1OC1C(OC)CC(O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O[C@@H]([C@@H](C)C(O)C4)C(C)C)O3)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)OC1C ZPAKHHSWIYDSBJ-QDXJZMFISA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- 150000002016 disaccharides Chemical class 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000013401 experimental design Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000003120 macrolide antibiotic agent Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000010413 mother solution Substances 0.000 description 1
- 239000000575 pesticide 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
- 230000003449 preventive effect Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
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Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
- Saccharide Compounds (AREA)
Abstract
The present invention relates to agricultural chemicals technical fields more particularly to a kind of avermectin B2a phosphorylation modification object and its preparation method and application.The structure of the phosphorylation modification object is that the hydrogen in avermectin B2a on all hydroxyls is replaced by phosphate group.Preparation method is that solution is made in avermectin B2a and phosphate, is reacted through electron beam irradiation.Avermectin B2a phosphorylation modification object in the present invention can be used as the drug of prevention and treatment root-knot nematode, and can be improved the yield of watermelon, improve quality of watermelon.
Description
Technical field
The invention belongs to agricultural chemicals technical fields, and in particular to a kind of avermectin B2a phosphorylation modification object and its
Preparation method and application.
Background technique
Avermectin (Avermectins) and its derivative belong to biological source insecticide, have sterilization, desinsection, mite killing etc.
Effect, to people and animals and Environmental security, is widely used in biological pesticide and veterinary drug.Avermectin is ten hexa-atomic macrolide disaccharide classes
Compound.Natural avermectin shares 8 components, according to the difference of substituent group on the position C5, C22, C23 and C25 to its 8
Component is respectively designated as A1a, A2a, B1a, B2a, A1b, A2b, B1b and B2b, wherein the drug effect of avermectin B component is compared with A group
Divide by force, the active highest of B1, insecticidal spectrum is most wide, and B2 takes second place, but mammal is most safe.Avermectin B2 is that microbial fermentation is raw
The accessory during AVERMECTIN B1 is produced, is the extract of AVERMECTIN B1 crystalline mother solution, by B2a and B2b at being grouped as,
Main active is avermectin B2a.Therefore, how to efficiently use avermectin B2a in the extra price for improving avermectin
It is of great significance in terms of value.
Avermectin B2a is reported in existing research at present has certain control efficiency for root nematode, but still needs into one
Step improves, meanwhile, avermectin B2a can also make individual plant yellow occur, burn phenomena such as root, so that its use has received limit
System.
Summary of the invention
For the bad problem of current avermectin B2a application effect, the present invention provides a kind of avermectin B2a phosphorylation
Modifier.
And the present invention also provides the preparation methods of above-mentioned avermectin B2a phosphorylation modification object.
And the answering as prevention and treatment root-knot nematode drug the present invention also provides above-mentioned avermectin B2a phosphorylation modification object
With.
And the present invention also provides above-mentioned avermectin B2a phosphorylation modification objects to improve the yield of watermelon and improve watermelon
Application in quality.
To achieve the above object of the invention, the embodiment of the present invention adopts the technical scheme that
A kind of avermectin B2a phosphorylation modification object, structural formula are as follows:
Wherein the structure of X isWherein Y is hydrogen ion or alkali metal ion.
After the phosphorylated modification of avermectin B2a, it may occur that the change in terms of chemical and biological activity, bioactivity mention
Height has more significant control efficiency for root nematode, and to plant without ill-effect, makes it in industrial production, agricultural insecticidal, green
Colour circle guarantor etc. has higher practical application value.Not yet discovery is about avermectin B2a phosphorylation modification object at present
Relevant report.
And the present invention also provides the preparation methods of above-mentioned avermectin B2a phosphorylation modification object, by avermectin B2a
Solution is made with phosphate, is reacted through electron beam irradiation.
The present invention using electron beam high-energy ray in solution avermectin B2a and phosphate irradiate, can
So that the phosphate radical in phosphate is replaced the hydrogen on avermectin B2a hydroxyl, the phosphorylation of avermectin B2a is repaired to can realize
Decorations, obtain avermectin B2a phosphorylation modification object.
Preferably, the dosage of the electron beam irradiation is 0.75~5.00kGy.The irradiation dose of the range can obtain compared with
High reaction yield.
Preferably, the dosage of the electron beam irradiation is 1.00~4.00kGy.Preferred electron beam irradiation dosage can be into
One step improves reaction yield.
Preferably, the dosage of the electron beam irradiation is 1.50kGy.Preferred irradiation dose can obtain optimal reaction
Yield.
Preferably, the phosphate is sodium phosphate, the mass ratio of the avermectin B2a and the sodium phosphate is 10: 1~
9；And/or the solvent be organic solvent and water mixed solution, the organic solvent be selected from methanol, ethyl alcohol, propyl alcohol, butanol,
At least one of acetone and isopropanol；And/or the pH of the solution is 6.0~10.0；And/or the temperature of the solution is 10
~80 DEG C；And/or the time of the reaction is 0.5~2.5h.Under the reaction condition of electron beam irradiation, sodium phosphate can make Ah
The reaction yield highest for tieing up rhzomorph B2a phosphorylation modification, in preferred quality than in range, can get higher reaction yield.
The solubility of avermectin B2a and phosphate in the above solvent is larger, is conducive to the two sufficiently dissolution, and avermectin
The free radical of B2a is easier to be crosslinked with phosphate radical and realize phosphorylation in the above solvent, is conducive to improve reaction yield.Excellent
Avermectin B2a and phosphatic reaction yield are higher in the pH of choosing, temperature and/or reaction time range.Wherein, hydrogen can be used
Sodium hydroxide solution adjusts pH value of solution, and otheralkali metal impurity will not be brought into product.
Preferably, the mass ratio of the avermectin B2a and the sodium phosphate is 10: 3~9；And/or the solvent is body
The ethyl alcohol that product percentage concentration is 92~97%；And/or the pH of the solution is 7.0~10.0；And/or the temperature of the solution is
40~80 DEG C；And/or the time of the reaction is 1.0~2.5h.Preferred mass ratio, pH, temperature, reaction time range can
Obtain higher reaction yield.Solvent can be avoided problem of solvent residual using ethyl alcohol, and product is made more to meet the neck such as agricultural, farm
Requirement of the domain to safety.
Preferably, which further includes that reaction products therefrom is concentrated, and precipitating is precipitated, is separated by solid-liquid separation, by institute
Solid is obtained to be dried.The subsequent operation can obtain solid product, be readily transported, store and use.
And the embodiment of the invention also provides above-mentioned avermectin B2a phosphorylation modification objects as prevention and treatment root-knot nematode
The application of drug.Avermectin B2a phosphorylation modification object has significant effect to the prevention and treatment of watermelon root-knot and increasing yield of water melons
Fruit, also, the avermectin B2a phosphorylation modification object is using efficient and convenient, to product and ecological environment security, suitable for producing
Upper large-scale application.
And the embodiment of the invention also provides above-mentioned avermectin B2a phosphorylation modification object improve the yield of watermelon and
Improve the application in quality of watermelon.After handling watermelon with avermectin B2a phosphorylation modification object, the upgrowth situation and mouth of watermelon
Sense, pol are obviously improved, and the maturity period shifts to an earlier date.
Detailed description of the invention
Fig. 1 is the infrared spectrogram of avermectin B2a phosphorylation modification object in avermectin B2a and the present invention.
Specific embodiment
In order to make the objectives, technical solutions, and advantages of the present invention clearer, below in conjunction with specific embodiment, to this
Invention is further elaborated.It should be appreciated that specific embodiment described herein is used only for explaining the present invention, not
For limiting the present invention.
Avermectin B2a used by the present embodiment comes from Hebei Mei He pharmaceutcal corporation, Ltd.
Embodiment 1
Present embodiments provide a kind of preparation method of avermectin B2a phosphorylation modification object.
Specifically includes the following steps:
10g avermectin B2a is dissolved in the ethyl alcohol (95%v/v) of 100ml, the sodium phosphate of 3.5g is added in solution, stirs
Dissolution is mixed, with 5% sodium hydroxide solution tune pH value to 8, solution temperature is set as 60 DEG C, which is put into irradiation platform, is led to
It crosses electron beam irradiation (electron beam 10MeV), irradiation dose 1.50kGy, after irradiation, controls reaction time 2h, then exist
Ethyl alcohol is boiled off on Rotary Evaporators, precipitating is precipitated, and filtering precipitating is dried in a vacuum drying oven, and temperature is no more than 60 DEG C, will do
Solid after dry adds 30ml ethyl alcohol to be recrystallized to get avermectin B2a phosphorylation modification object is arrived.
Embodiment 2
Present embodiments provide a kind of preparation method of avermectin B2a phosphorylation modification object.
Specifically includes the following steps:
10g avermectin B2a is dissolved in the ethyl alcohol (92%v/v) of 100ml, the sodium phosphate of 7g, stirring are added in solution
Dissolution, with 5% sodium hydroxide solution tune pH value to 6, sets solution temperature as 40 DEG C, which is put into irradiation platform, is passed through
Electron beam irradiation (electron beam 10MeV), irradiation dose 1.00kGy after irradiation, control reaction time 0.5h, then exist
Ethyl alcohol is boiled off on Rotary Evaporators, precipitating is precipitated, and filtering precipitating is dried in a vacuum drying oven, and temperature is no more than 60 DEG C, will do
Solid after dry adds 30ml ethyl alcohol to be recrystallized to get avermectin B2a phosphorylation modification object is arrived.
Embodiment 3
Present embodiments provide a kind of preparation method of avermectin B2a phosphorylation modification object.
Specifically includes the following steps:
10g avermectin B2a is dissolved in the ethyl alcohol (95%v/v) of 100ml, the sodium phosphate of 3g, stirring are added in solution
Dissolution, with 5% sodium hydroxide solution tune pH value to 8, sets solution temperature as 60 DEG C, which is put into irradiation platform, is passed through
Electron beam irradiation (electron beam 10MeV), irradiation dose 1.50kGy after irradiation, control reaction time 1.5h, then exist
Ethyl alcohol is boiled off on Rotary Evaporators, precipitating is precipitated, and filtering precipitating is dried in a vacuum drying oven, and temperature is no more than 60 DEG C, will do
Solid after dry adds 30ml ethyl alcohol to be recrystallized to get avermectin B2a phosphorylation modification object is arrived.
Embodiment 4
Present embodiments provide a kind of preparation method of avermectin B2a phosphorylation modification object.
Specifically includes the following steps:
10g avermectin B2a is dissolved in the ethyl alcohol (95%v/v) of 100ml, the sodium phosphate of 5g, stirring are added in solution
Dissolution, with 5% sodium hydroxide solution tune pH value to 9, sets solution temperature as 10 DEG C, which is put into irradiation platform, is passed through
Electron beam irradiation (electron beam 10MeV), irradiation dose 4.00kGy after irradiation, control reaction time 2.5h, then exist
Ethyl alcohol is boiled off on Rotary Evaporators, precipitating is precipitated, and filtering precipitating is dried in a vacuum drying oven, and temperature is no more than 60 DEG C, will do
Solid after dry adds 30ml ethyl alcohol to be recrystallized to get avermectin B2a phosphorylation modification object is arrived.
Embodiment 5
Present embodiments provide a kind of preparation method of avermectin B2a phosphorylation modification object.
Specifically includes the following steps:
10g avermectin B2a is dissolved in the ethyl alcohol (95%v/v) of 100ml, the sodium phosphate of 9g, stirring are added in solution
Dissolution, with 5% sodium hydroxide solution tune pH value to 10, sets solution temperature as 80 DEG C, which is put into irradiation platform, is passed through
Electron beam irradiation (electron beam 10MeV), irradiation dose 5.00kGy after irradiation, control reaction time 1h, are then revolving
Turn to boil off ethyl alcohol on evaporimeter, precipitating is precipitated, filtering precipitating is dried in a vacuum drying oven, and temperature is no more than 60 DEG C, will dry
Solid afterwards adds 30ml ethyl alcohol to be recrystallized to get avermectin B2a phosphorylation modification object is arrived.
Embodiment 6
Present embodiments provide a kind of preparation method of avermectin B2a phosphorylation modification object.
Specifically includes the following steps:
10g avermectin B2a is dissolved in the ethyl alcohol (97%v/v) of 100ml, the sodium phosphate of 1g, stirring are added in solution
Dissolution, with 5% sodium hydroxide solution tune pH value to 7, sets solution temperature as 50 DEG C, which is put into irradiation platform, is passed through
Electron beam irradiation (electron beam 10MeV), irradiation dose 0.75kGy after irradiation, control reaction time 2h, are then revolving
Turn to boil off ethyl alcohol on evaporimeter, precipitating is precipitated, filtering precipitating is dried in a vacuum drying oven, and temperature is no more than 60 DEG C, will dry
Solid afterwards adds 30ml ethyl alcohol to be recrystallized to get avermectin B2a phosphorylation modification object is arrived.
Product test
Products therefrom of the present invention is subjected to infrared analysis, and is compared with avermectin B2a, gained infrared spectrogram is such as
Shown in Fig. 1.As seen from Figure 1, in 4000~400cm-1Wave-number range in, before and after avermectin B2a phosphorylation in 3416,
2067、1618、1401、1153、618cm-1Apparent absorption peak can be detected in place, they are due to hydroxyl O-H (including phosphate radical
On H in the O and solvent that are not connect with avermectin B2a be formed by the hydroxyl in hydroxyl and solvent molecule), carbonyl C-O
Caused by equal groups stretching vibration.Containing the hydroxyl for being connected in phenyl ring in avermectin B2a, absorption peak is located at 483.91cm-1Place,
After phosphorylated modification, the hydrogen in avermectin B2a in all hydroxyls is replaced by phosphate radical, therefore avermectin B2a phosphorylation
The absorption peak disappears in modifier.
The infrared absorption peak of phosphate radical is in 1100~920cm-1Near, from figure 1 it appears that phosphorylation avermectin
The phosphate radical absorption peak of B2a is in 1066.65cm-1Left and right.891.13cm-1 locating absorption peak is caused by the stretching vibration of P-O-C
's.
The reaction yield for investigating above embodiments 1~6, the results are shown in Table 1.
The reaction yield of 1 Examples 1 to 6 of table
| Embodiment | Embodiment 1 | Embodiment 2 | Embodiment 3 | Embodiment 4 | Embodiment 5 | Embodiment 6 |
| Yield (%) | 89.50 | 82.41 | 88.70 | 83.37 | 84.25 | 81.70 |
By 1 result of table as it can be seen that preparing avermectin B2a phosphorylation modification with the preparation method of the embodiment of the present invention 1~6
Object, yield can reach 81.70%, it was demonstrated that the preparation method of avermectin B2a phosphorylation modification object provided by the present invention has
Higher yields, the large-scale production for avermectin B2a phosphorylation modification object have good feasibility and economic value.
Embodiment 7
Since harm of the root-knot nematode in watermelon is the most obvious, therefore the present embodiment is provided using watermelon as investigation object
Avermectin B2a phosphorylation modification object is as the application for preventing and treating root-knot nematode drug in the present invention.
1, experimental plot overview
Experimental plot is located in suburbs peasant household, Yuzhou of Henan city greenhouse, and soil property is clay, and plantation watermelon 10 years or more, for many years
Carry out root-knot nematode to occur seriously, individual times, which once cause to drop in production over a large area, even has no harvest.
Experimental plot watermelon is aspermous watermelon, is transplanted July, and planting density is 7000 plants/hm2。
The varieties of plant in simultaneous selection and experimental plot, fertilizer and water management and other cultivation conditions two pieces of growth of watermelon all the same
Field, respectively as control field and blank field.Between experimental plot, control field and blank field and its surrounding is respectively provided with protection row, avoids
Outside is to generation interference between watermelon field or each field.
2, test material
1 gained avermectin B2a phosphorylation modification object of avermectin B2a and embodiment without phosphorylation modification.
3, experimental design
Avermectin B2a and avermectin B2a phosphorylation modification are applied in cave when watermelon is transplanted in control field and experimental plot
Object, amount of application are 0.25g/ plants；Blank field is not administered.
4, investigation statistics
2d carries out incidence inspection before watermelon harvests (September).Using five point sampling, experimental plot, control field and sky
White field respectively investigates 10 plants, record morbidity sum of series morbidity strain number.
0 grade, root system is without insect gall；
1 grade, root system has a small amount of small insect gall；
3 grades, 2/3 root system is covered with small insect gall；
5 grades, root system is covered with small insect gall and has secondary insect gall；
7 grades, root system forms fibrous root group.
Drug effect is examined, calculation formula is as follows:
Disease index=(diseased plant numbers at different levels × relative level value)/(investigation total strain number × 7) × 100%；
Control efficiency=(check plot disease index-treatment region disease index)/check plot disease index × 100%
The root-knot nematode incidence of each piece of watermelon field is as shown in table 2.
Table 2 investigates result to the control efficiency of watermelon root-knot
As can be seen from Table 2, there are good preventive and therapeutic effect, control efficiency difference in control field and experimental plot to watermelon root-knot disease
For 83.32% and 90.07%, the two significant difference illustrates that 1 gained avermectin B2a phosphorylation modification object of embodiment is being prevented and treated
Watermelon root-knot disease aspect has the effect of better than avermectin B2a.
5, safety evaluatio
The upgrowth situation of each Tanaka's watermelon is observed after application: experimental plot does not occur phytotoxicity in watermelon seedling stage and Later growth
Symptom, leaf color is dark green, growth is vigorous.There is yellow and burn root phenomenon in individual plant after administration in control field；Blank field leaf color
Pale green, growth potential are weak, and individual plant noons wilt.Avermectin B2a and avermectin B2a phosphorylation modification object are for right
It has no adverse effects according to other pest and disease damages in field and experimental plot and non-target organism.The result illustrates that avermectin B2a phosphorylation is repaired
Jewelry is suitable for producing upper large-scale application to product and ecological environment security.
Embodiment 8
The present embodiment provides avermectin B2a phosphorylation in the present invention using the watermelon in embodiment 7 as investigation object
Modifier is improving the yield of watermelon and is improving the application in quality of watermelon.
Examine the influence in embodiment 7 after each field medication to the yield, quality of watermelon
Harvest time range estimation investigation watermelon overground part plant growing way；Meanwhile experimental plot, control field and blank field respectively take 3 west
Melon, weighing conversion the yield of watermelon, the results are shown in Table 3.
Open watermelon, range estimation investigation melon pulp color；Watermelon mouthfeel is examined by tasting；Each processing is measured with digital display saccharous detector
The pol of watermelon, the results are shown in Table 4.
The investigation result of 3 the yield of watermelon of table
| Group | Single melon weight/kg | Equivalent yield/kghm-2 | Compared with the growth rate/% in blank field |
| Compare field | 7.01 | 47784.9 | 22.62 |
| Experimental plot | 7.13 | 48876.8 | 25.43 |
| Blank field | 5.98 | 38967.4 | / |
The investigation result of 4 quality of watermelon of table
By 3 result of table as it can be seen that the yield of watermelon in control field and experimental plot is respectively 47784.9,48876.8kg/hm2,
There is obvious volume increase compared with blank field, amount of increase in production is respectively 22.62%, 25.43%, obvious effect of increasing production, and compares field and test
Effect of increasing production significant difference between field illustrates 1 gained avermectin B2a phosphorylation modification object of embodiment in terms of increasing yield of water melons
Have the effect of better than avermectin B2a.
By 4 result of table as it can be seen that experimental plot shows well in melon pulp color, maturity, mouthfeel, sugariness, it is significantly better than
Field and blank field are compareed, and the maturity period shifts to an earlier date.
The foregoing is merely illustrative of the preferred embodiments of the present invention, is not intended to limit the invention, all in essence of the invention
Made any modification, equivalent replacement or improvement etc., should all be included in the protection scope of the present invention within mind and principle.
Claims (10)
1. a kind of avermectin B2a phosphorylation modification object, which is characterized in that its structural formula is as follows:
Wherein the structure of X isWherein Y is hydrogen ion or alkali metal ion.
2. the preparation method of avermectin B2a phosphorylation modification object described in a kind of claim 1, which is characterized in that by Avermectin
Solution is made in plain B2a and phosphate, reacts through electron beam irradiation.
3. the preparation method of avermectin B2a phosphorylation modification object according to claim 2, which is characterized in that the electronics
The dosage of beam irradiation is 0.75~5.00kGy.
4. the preparation method of avermectin B2a phosphorylation modification object according to claim 3, which is characterized in that the electronics
The dosage of beam irradiation is 1.00~4.00kGy.
5. the preparation method of avermectin B2a phosphorylation modification object according to claim 4, which is characterized in that the electronics
The dosage of beam irradiation is 1.50kGy.
6. according to the preparation method of any one of the claim 2~5 avermectin B2a phosphorylation modification object, which is characterized in that
The phosphate is sodium phosphate, and the mass ratio of the avermectin B2a and the sodium phosphate is 10: 1~9；And/or
The solvent is the mixed solution of organic solvent and water, and the organic solvent is selected from methanol, ethyl alcohol, propyl alcohol, butanol, acetone
At least one of with isopropanol；And/or
The pH of the solution is 6.0~10.0；And/or
The temperature of the solution is 10~80 DEG C；And/or
The time of the reaction is 0.5~2.5h.
7. the preparation method of avermectin B2a phosphorylation modification object according to claim 6, which is characterized in that the AVM hereinafter
The mass ratio of rhzomorph B2a and the sodium phosphate is 10: 3~9；And/or
The mixed solution is the ethyl alcohol that concentration expressed in percentage by volume is 92~97%；And/or
The pH of the solution is 7.0~10.0；And/or
The temperature of the solution is 40~80 DEG C；And/or
The time of the reaction is 1.0~2.5h.
8. according to the preparation method of any one of the claim 2~5 avermectin B2a phosphorylation modification object, which is characterized in that
Further include that reaction products therefrom is concentrated, precipitating is precipitated, is separated by solid-liquid separation, obtained solid is dried.
9. application of the avermectin B2a phosphorylation modification object described in claim 1 as prevention and treatment root-knot nematode drug.
10. avermectin B2a phosphorylation modification object described in claim 1 is improving the yield of watermelon and is improving answering in quality of watermelon
With.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115624031A (en) * | 2022-10-14 | 2023-01-20 | 河北威远生物化工有限公司 | Methylamino avermectin B 2a And application of salt compound thereof |
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| US4469682A (en) * | 1983-01-28 | 1984-09-04 | Merck & Co., Inc. | Avermectin and milbemycin phosphate esters, pharmaceutical compositions, and method of use |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US4469682A (en) * | 1983-01-28 | 1984-09-04 | Merck & Co., Inc. | Avermectin and milbemycin phosphate esters, pharmaceutical compositions, and method of use |
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| YANLI DENG ET AL.: "House Fly Head GABA-Gated Chloride Channel: Toxicologically Relevant Binding Site for Avermectins Coupled to Site for Ethynylbicycloorthobenzoate", 《PESTICIDES BIOCHEMISTRY AND PHYSIOLOGY》 * |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115624031A (en) * | 2022-10-14 | 2023-01-20 | 河北威远生物化工有限公司 | Methylamino avermectin B 2a And application of salt compound thereof |
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