CN104926753A - Thidiazuron sulfonate and application thereof - Google Patents
Thidiazuron sulfonate and application thereof Download PDFInfo
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- CN104926753A CN104926753A CN201510134154.4A CN201510134154A CN104926753A CN 104926753 A CN104926753 A CN 104926753A CN 201510134154 A CN201510134154 A CN 201510134154A CN 104926753 A CN104926753 A CN 104926753A
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- thidiazuron
- formula
- sulfonate
- compound
- plant
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- HFCYZXMHUIHAQI-UHFFFAOYSA-N Thidiazuron Chemical compound C=1C=CC=CC=1NC(=O)NC1=CN=NS1 HFCYZXMHUIHAQI-UHFFFAOYSA-N 0.000 title claims abstract description 34
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 title claims abstract description 21
- 239000005648 plant growth regulator Substances 0.000 claims abstract description 9
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 9
- 230000032823 cell division Effects 0.000 claims abstract description 5
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 230000001737 promoting effect Effects 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 25
- 230000000694 effects Effects 0.000 abstract description 10
- 235000017060 Arachis glabrata Nutrition 0.000 abstract description 8
- 244000105624 Arachis hypogaea Species 0.000 abstract description 8
- 235000010777 Arachis hypogaea Nutrition 0.000 abstract description 8
- 235000018262 Arachis monticola Nutrition 0.000 abstract description 8
- 235000020232 peanut Nutrition 0.000 abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 8
- 238000012360 testing method Methods 0.000 abstract description 6
- 240000008067 Cucumis sativus Species 0.000 abstract description 5
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 abstract description 5
- 230000012010 growth Effects 0.000 abstract description 4
- 230000008901 benefit Effects 0.000 abstract description 2
- 231100000674 Phytotoxicity Toxicity 0.000 abstract 1
- UQHKFADEQIVWID-UHFFFAOYSA-N cytokinin Natural products C1=NC=2C(NCC=C(CO)C)=NC=NC=2N1C1CC(O)C(CO)O1 UQHKFADEQIVWID-UHFFFAOYSA-N 0.000 abstract 1
- 239000004062 cytokinin Substances 0.000 abstract 1
- 238000011981 development test Methods 0.000 abstract 1
- 230000008635 plant growth Effects 0.000 abstract 1
- 230000001105 regulatory effect Effects 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- -1 thidiazuron sulfonic acid ammonium salt Chemical class 0.000 description 9
- 238000003756 stirring Methods 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000003337 fertilizer Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 4
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000000967 suction filtration Methods 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 3
- 239000008399 tap water Substances 0.000 description 3
- 235000020679 tap water Nutrition 0.000 description 3
- GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 235000009754 Vitis X bourquina Nutrition 0.000 description 2
- 235000012333 Vitis X labruscana Nutrition 0.000 description 2
- 240000006365 Vitis vinifera Species 0.000 description 2
- 235000014787 Vitis vinifera Nutrition 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 0 *c(cc1)ccc1NC(Nc1cnn[s]1)=O Chemical compound *c(cc1)ccc1NC(Nc1cnn[s]1)=O 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- RNMDNPCBIKJCQP-UHFFFAOYSA-N 5-nonyl-7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-ol Chemical compound C(CCCCCCCC)C1=C2C(=C(C=C1)O)O2 RNMDNPCBIKJCQP-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 239000005979 Forchlorfenuron Substances 0.000 description 1
- NWBJYWHLCVSVIJ-UHFFFAOYSA-N N-benzyladenine Chemical compound N=1C=NC=2NC=NC=2C=1NCC1=CC=CC=C1 NWBJYWHLCVSVIJ-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000003416 augmentation Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000002837 defoliant Substances 0.000 description 1
- 230000035613 defoliation Effects 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000004992 fission Effects 0.000 description 1
- GPXLRLUVLMHHIK-UHFFFAOYSA-N forchlorfenuron Chemical compound C1=NC(Cl)=CC(NC(=O)NC=2C=CC=CC=2)=C1 GPXLRLUVLMHHIK-UHFFFAOYSA-N 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 230000000394 mitotic effect Effects 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229930195732 phytohormone Natural products 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A40/00—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production
- Y02A40/10—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production in agriculture
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
The invention discloses a thidiazuron sulfonate with a structure represented by a formula I, and an application thereof as a plant growth regulator. In the formula, M is selected from K, Na or NH4. As a result of a cucumber cotyledon expansion test and a peanut growth and development test, the compound represented by the formula I can significantly promote cell division and effectively regulating plant growth. As a cytokinin, the compound of the formula I has the advantages of high activity, high water solubility, less possibility of phytotoxicity, low cost, and low residue.
Description
Technical field
The invention belongs to plant-growth regulator field in agricultural chemicals, be specifically related to a kind of thidiazuron sulfonate and uses thereof.
Background technology
Phytokinin, as the important kind in plant-growth regulator, has the effect promoting cell fission, increasing yield and improving quality and strengthen crop anti-adversity.Current commercial phytokinin, as 6-benzyl aminopurine, forchlorfenuron and thidiazuron etc., though activity is higher, is water-insoluble, and safety in utilization is poor and be difficult to and other active ingredient compatibilities., although have water-soluble and safety in utilization, its cell division activity is not ideal enough for the sym-diphenylurea sulfonate (formula II compound) of recent report.In the prior art, thidiazuron sulfonate (type I compound) as representative of the present invention and cell division activity thereof have no report.
Summary of the invention
The object of this invention is to provide a kind of novel structure, prepare easy, use safety, efficient and water miscible thidiazuron sulfonate plant-growth regulator, it is mainly used as phytokinin and promotes crop yield.
Thidiazuron is mainly used as cotton defoliant at present, for the cotton defoliation in cotton ripening stage, research in recent years finds, it has good cell division activity when lower concentration, but this compound pole is insoluble in water, be difficult to the aqua preparation developing greenization, also not easily combine stable aqua product with other foliage fertilizers.The present invention is by phenyl ring introducing sulfonic group in thidiazuron structure, be prepared into water miscible thidiazuron sodium sulfonate, potassium or ammonium salt, not only overcome the deficiency that thidiazuron exists, also improve its work safety, good compatibleness is had with acid, alkaline and neutral foliage fertilizer, both widen its range of application, be also conducive to the lifting of product comprehensive function.
Technical scheme of the present invention is as follows:
The invention provides a kind of thidiazuron sulfonate, structure is as shown in formula I:
In formula: M is selected from K, Na or NH
4.
Type I compound can be obtained by following reaction:
In formula, M definition is the same.
Thidiazuron generates thidiazuron sulfonic acid with chlorosulfuric acid in methylene dichloride (or ethylene dichloride), control temperature 10-20 DEG C, with 20% sodium hydroxide, 20% potassium hydroxide or ammonia neutralization to pH value 7, steam solvent, refluxing toluene dewaters to obtain white solid, obtains type I compound of the present invention through Virahol purifying.
Advantage of the present invention and positively effect:
Compared with known compound thidiazuron, type I compound of the present invention is soluble in water, the various concentration thidiazuron sulfonate aqueous solution can be configured to as required, also can with other various foliage fertilizers, rush the compatibility such as to apply fertilizer and form the functional product had good stability, this is that known compound thidiazuron is difficult to realize.
Wheat seed root test in, thidiazuron shows serious suppression and takes root and germinate under 1-30ppm concentration, type I compound of the present invention then has good growth-promoting root performance and higher percentage of germination, illustrates that type I compound of the present invention has higher safety in utilization and wider concentration use range; Compared with known formula II compound (sym-diphenylurea sulfonate), formula I Compound cellular mitotic activity is significantly better than known formula II compound (data are in table 1).Field test shows, sprays 2-3 time, can make wheat increase yield 12.3% under type I compound 5ppm concentration of the present invention in vegetative period, corn yield increasing 15.8%, peanut yield increasing 17.1%, can make grape yield increasing 25.7% and precocious 5 days, the painted and mouthfeel of grape is obviously improved.
In sum, type I compound of the present invention not only has the comprehensive function of volume increase, precocious and upgrading, and has positively effects such as producing easy, use cost is low, safe ready, is a kind of efficient plant growth regulator with commercialization and market potential.
Formula I, when using as plant-growth regulator, can be used alone, and also can combinationally use with other active ingredients or foliage fertilizer, to provide the comprehensive function of product.
When preparing aqua preparation, usually add proper amount of surfactant and agriculture or forestry acceptable carrier.
Should it is clear that, in claim limited range of the present invention, can various conversion and change be carried out.
Embodiment
Following synthetic example and raw test-results of surveying can be used to further illustrate the present invention, but do not mean that restriction the present invention.
Synthesis example:
The preparation of example 1, type I compound
(1) preparation of thidiazuron sulfonic acid potassium salt
22.00g (0.1mol) N-phenyl-N-1 is added respectively in 250mL there-necked flask, 2,3-thiadiazoles-5-urea (thidiazuron) and 100mL methylene dichloride, the solution be made up of 12.82g (0.11mol) chlorsulfonic acid and 30mL methylene dichloride is dripped under stirring at room temperature, molten complete, at 20-40 DEG C of stirring reaction 3h, with 20%KOH solution temperature control less than 20 DEG C, reaction solution is neutralized to about pH=7.Revolve and steam removing methylene chloride, refluxing toluene dehydration is extremely anhydrous, suction filtration, dry, obtain white solid, by gained solid 150mL Virahol heating for dissolving, filtering insolubles (inorganic salt) while hot, filtrate naturally cools to room temperature, suction filtration, filter cake with appropriate isopropyl alcohol wash once, suction filtration, dry, obtain white solid powder 26.50g, productive rate 88.3%.Fusing point: 224-226 DEG C.
1H NMR(500MHz,DMSO)，δ/ppm：8.201(1H，Thiazolyl-H)，7.912-7.921(4H，m，H-Ar)，6.05(2H，-NH)。
(2) preparation of thidiazuron sulfonate sodium
Replace methylene dichloride with ethylene dichloride, adopt aforesaid method to prepare thidiazuron sulfonic acid, then with 20%NaOH solution, reaction solution is neutralized to about pH=7.Revolve and steam except desolventizing ethylene dichloride, refluxing toluene dehydration is to anhydrous, and suction filtration, with recrystallisation from isopropanol, obtains white solid powder thidiazuron sodium sulfonate.
Replace sodium hydroxide with strong aqua, according to above method, thidiazuron sulfonic acid ammonium salt can be obtained.
Prepared by example 2, thidiazuron sulfonate aqua
(1) 2% thidiazuron sulfonic acid potassium salt aqua preparation
Take 2.0g thidiazuron sulfonic acid potassium salt, add 93g tap water, stirring and dissolving, to clear solution, then adds 5g tween-80, stirs and obtains 2% thidiazuron sulfonic acid potassium salt aqua.
(2) 5% thidiazuron sulfonate sodium aqua preparations
Take 5.0g thidiazuron sulfonate sodium, add 90g tap water, stirring and dissolving, then add 5gNP-10 (polyoxyethylene nonylphenol ether), namely stirring and dissolving to clear obtains 5% thidiazuron sulfonate sodium aqua.
(3) 10% thidiazuron sulfonic acid ammonium salt aqua preparations
Take 10g thidiazuron sulfonic acid ammonium salt, add 80g tap water, stirring and dissolving, to clear solution, then adds 10g alkyl glycoside, stirs and obtains 10% thidiazuron sulfonic acid ammonium salt aqua.
Biological activity determination
Example 3, cucumber cotyledons augmentation test
Supply examination cucumber variety to be that Tianjin grinds No. 4, after seed soaking, sowing is in the enamel tray with cover filling 0.7% agar, and cultivate 72h under being placed in 26 DEG C of dark situations, the cotyledon of selected size uniformity is stand-by, the filter paper enzyme in sample preparation employing phytohormone activity substance-measuring.
Specific practice is: type I compound thidiazuron sulfonate and formula II potassium Compound Salt are prepared as 100 μ gmL
-1, 10 μ gmL
-1the aqueous solution.Getting each mother liquor 0.3mL respectively evenly drips on the filter paper of Φ 6cm, after solvent is air-dry, in the culture dish of Φ 6cm, respectively puts into the filter paper 1 containing sample, adds distilled water 3mL, cotyledon 10, be 100 and 10 μ gmL
-1process.Take distilled water as contrast, be placed in 26 DEG C, cultivate under 3000Lux light intensity environment, after 72h, measure every 10 slice, thin piece leaf fresh weights.Often process and repeat for 2 times, results averaged, test-results is in table 1.
Table 1 cucumber cotyledons expansion simultaneous test
From table 1 testing data, type I compound of the present invention is significantly better than contrast II compound to cucumber cotyledons expansion activity.
Example 4, Development of Peanut are tested
At the aqueous solution of peanut seedling spraying thidiazuron sulfonate, investigate the impact on Development of Peanut, spraying concentration is 20ppm, and the results are shown in Table 2.
Table 2 Development of Peanut is tested
| Compound | Plant height (cm) | Side shoot long (cm) | Branch amount (bar) | Individual plant flower amount (piece) | Individual plant young fruit number (individual) |
| Type I compound sylvite | 14.7 | 21.6 | 12 | 34 | 26 |
| Type I compound sodium salt | 15.3 | 22.0 | 13 | 35 | 27 |
| Type I compound ammonium salt | 15.0 | 22.0 | 12 | 35 | 26 |
| Clear water contrasts | 11.8 | 17.0 | 7 | 24 | 20 |
As can be seen from Table 2, after spraying the compounds of this invention, obviously facilitate the robust growth of peanut, absolutely prove that the compounds of this invention can regulate and control peanut nutrition growth and reproductive growth, for increasing yield and improving quality has laid solid foundation effectively as plant-growth regulator.
Claims (3)
1. a thidiazuron sulfonate, structure is as shown in general formula I:
In formula: M is selected from K, Na or NH
4.
2. the purposes of a kind of thidiazuron sulfonate according to claim 1, is characterized in that formula I can be used as plant-growth regulator for promoting plant cell division and crop yield.
3. a plant growth regulator composition, containing formula I according to claim 1 as acceptable carrier in active ingredient and agricultural or forestry.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510134154.4A CN104926753A (en) | 2015-03-26 | 2015-03-26 | Thidiazuron sulfonate and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510134154.4A CN104926753A (en) | 2015-03-26 | 2015-03-26 | Thidiazuron sulfonate and application thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN104926753A true CN104926753A (en) | 2015-09-23 |
Family
ID=54114208
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510134154.4A Pending CN104926753A (en) | 2015-03-26 | 2015-03-26 | Thidiazuron sulfonate and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104926753A (en) |
-
2015
- 2015-03-26 CN CN201510134154.4A patent/CN104926753A/en active Pending
Non-Patent Citations (2)
| Title |
|---|
| -: "RN 1171964-41-2 & RN 1024322-50-6 & RN 885879-26-5 & RN 676584-88-6 & RN 675827-14-2 & RN 674788-43-3", 《STN REGISTRY》 * |
| PRIYAMVADA ACHARYA ET AL.: "Structure-Based Identification and Neutralization Mechanism of Tyrosine Sulfate Mimetics That Inhibit HIV-1 Entry", 《ACS CHEMICAL BIOLOGY》 * |
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Application publication date: 20150923 |