CN116874541B - Plant growth regulator and preparation method thereof - Google Patents
Plant growth regulator and preparation method thereof Download PDFInfo
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- CN116874541B CN116874541B CN202310874901.2A CN202310874901A CN116874541B CN 116874541 B CN116874541 B CN 116874541B CN 202310874901 A CN202310874901 A CN 202310874901A CN 116874541 B CN116874541 B CN 116874541B
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- 238000002360 preparation method Methods 0.000 title claims abstract description 14
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- 230000001737 promoting effect Effects 0.000 claims abstract description 23
- 230000008635 plant growth Effects 0.000 claims abstract description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 26
- 239000002904 solvent Substances 0.000 claims description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 21
- 239000003617 indole-3-acetic acid Substances 0.000 claims description 16
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 14
- 230000035784 germination Effects 0.000 claims description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
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- 235000021307 Triticum Nutrition 0.000 claims description 9
- LUAQTQAFUORQHV-UHFFFAOYSA-N 2h-pyrazolo[3,4-b]pyridin-3-amine Chemical compound C1=CC=C2C(N)=NNC2=N1 LUAQTQAFUORQHV-UHFFFAOYSA-N 0.000 claims description 7
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 7
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- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 2
- 229940023877 zeatin Drugs 0.000 description 2
- IVHKSUMLZQXFPR-UHFFFAOYSA-N 1-(4-methylphenyl)-n-(2-oxo-1-propyl-3,4-dihydroquinolin-6-yl)methanesulfonamide Chemical compound C=1C=C2N(CCC)C(=O)CCC2=CC=1NS(=O)(=O)CC1=CC=C(C)C=C1 IVHKSUMLZQXFPR-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 description 1
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- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 235000004936 Bromus mango Nutrition 0.000 description 1
- 244000241235 Citrullus lanatus Species 0.000 description 1
- 235000012828 Citrullus lanatus var citroides Nutrition 0.000 description 1
- 208000035240 Disease Resistance Diseases 0.000 description 1
- 241000189458 Dothidea Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- 229930191978 Gibberellin Natural products 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 241000282414 Homo sapiens Species 0.000 description 1
- 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 1
- 240000007228 Mangifera indica Species 0.000 description 1
- 235000014826 Mangifera indica Nutrition 0.000 description 1
- 108010002519 Prolactin Receptors Proteins 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 235000009184 Spondias indica Nutrition 0.000 description 1
- 241000562516 Thisbe Species 0.000 description 1
- CYAYKKUWALRRPA-RGDJUOJXSA-N [(2r,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-bromooxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@H]1O[C@H](Br)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O CYAYKKUWALRRPA-RGDJUOJXSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
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- 238000004166 bioassay Methods 0.000 description 1
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- JIJAYWGYIDJVJI-UHFFFAOYSA-N butyl naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)OCCCC)=CC=CC2=C1 JIJAYWGYIDJVJI-UHFFFAOYSA-N 0.000 description 1
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
- 238000012272 crop production Methods 0.000 description 1
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- 230000035613 defoliation Effects 0.000 description 1
- FCRACOPGPMPSHN-UHFFFAOYSA-N desoxyabscisic acid Natural products OC(=O)C=C(C)C=CC1C(C)=CC(=O)CC1(C)C FCRACOPGPMPSHN-UHFFFAOYSA-N 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- SYELZBGXAIXKHU-UHFFFAOYSA-N dodecyldimethylamine N-oxide Chemical compound CCCCCCCCCCCC[N+](C)(C)[O-] SYELZBGXAIXKHU-UHFFFAOYSA-N 0.000 description 1
- 230000005059 dormancy Effects 0.000 description 1
- 230000024346 drought recovery Effects 0.000 description 1
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- 230000008014 freezing Effects 0.000 description 1
- IXORZMNAPKEEDV-UHFFFAOYSA-N gibberellic acid GA3 Natural products OC(=O)C1C2(C3)CC(=C)C3(O)CCC2C2(C=CC3O)C1C3(C)C(=O)O2 IXORZMNAPKEEDV-UHFFFAOYSA-N 0.000 description 1
- 239000003448 gibberellin Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 150000008131 glucosides Chemical class 0.000 description 1
- 208000037824 growth disorder Diseases 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
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- 238000001727 in vivo Methods 0.000 description 1
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- 239000010410 layer Substances 0.000 description 1
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- 239000000787 lecithin Substances 0.000 description 1
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- 238000002789 length control Methods 0.000 description 1
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- 244000052769 pathogen Species 0.000 description 1
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- 239000000575 pesticide Substances 0.000 description 1
- 230000008121 plant development Effects 0.000 description 1
- 239000003375 plant hormone Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 230000014284 seed dormancy process Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- RUQIYMSRQQCKIK-UHFFFAOYSA-M sodium;2,3-di(propan-2-yl)naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(C(C)C)C(C(C)C)=CC2=C1 RUQIYMSRQQCKIK-UHFFFAOYSA-M 0.000 description 1
- NHQVTOYJPBRYNG-UHFFFAOYSA-M sodium;2,4,7-tri(propan-2-yl)naphthalene-1-sulfonate Chemical compound [Na+].CC(C)C1=CC(C(C)C)=C(S([O-])(=O)=O)C2=CC(C(C)C)=CC=C21 NHQVTOYJPBRYNG-UHFFFAOYSA-M 0.000 description 1
- HEBRGEBJCIKEKX-UHFFFAOYSA-M sodium;2-hexadecylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O HEBRGEBJCIKEKX-UHFFFAOYSA-M 0.000 description 1
- NWZBFJYXRGSRGD-UHFFFAOYSA-M sodium;octadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCOS([O-])(=O)=O NWZBFJYXRGSRGD-UHFFFAOYSA-M 0.000 description 1
- AYFACLKQYVTXNS-UHFFFAOYSA-M sodium;tetradecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCCCS([O-])(=O)=O AYFACLKQYVTXNS-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- UZKQTCBAMSWPJD-FARCUNLSSA-N trans-zeatin Chemical compound OCC(/C)=C/CNC1=NC=NC2=C1N=CN2 UZKQTCBAMSWPJD-FARCUNLSSA-N 0.000 description 1
- 244000045561 useful plants Species 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/12—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by acids having the group -X-C(=X)-X-, or halides thereof, in which each X means nitrogen, oxygen, sulfur, selenium or tellurium, e.g. carbonic acid, carbamic acid
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P21/00—Plant growth regulators
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
-
- 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
Abstract
The invention provides a plant growth regulator and a preparation method thereof, belonging to the technical field of plant growth regulators. Has the following structure; the novel glucoside compound is synthesized by the invention, the preparation method is simple, the synthesis condition is mild, the yield is higher, the prepared compound has better effects of promoting plant growth, improving plant stress resistance and improving plant yield, and also has certain antibacterial and bacteriostatic properties, and due to the introduction of glycosyl, the compound is safer and more environment-friendly, and almost has no toxic or side effect.
Description
Technical Field
The invention relates to the technical field of plant growth regulators, in particular to a plant growth regulator and a preparation method thereof.
Background
Plant growth regulators are a class of substances used to regulate plant growth and development, including synthetic compounds and natural plant hormones extracted from organisms. In plant cultivation, the plant growth regulator with lower concentration can play different roles of promoting, delaying or inhibiting, thereby achieving the purposes of rooting, sprouting, increasing yield, improving stress resistance and the like. Meanwhile, the plant growth regulator can also effectively solve the difficult problems in the cultivation technology, and particularly plays a positive role in breaking seed dormancy, promoting plant growth, overcoming the limit of crop production environment and improving harvesting and storage conditions.
For the target plant, the plant growth regulator is an exogenous non-nutritional chemical substance which can be generally transmitted to the action part in the plant body, and can promote or inhibit certain links of the life process of the target plant at a very low concentration, so that the target plant is in line with the needs of human beings. Each plant growth regulator has specific application and quite strict application technical requirements, and can only generate specific effects on target plants under specific application conditions (including external factors). Often, varying the concentration will give the opposite result, e.g. a promoting effect at low concentrations and an inhibiting effect at high concentrations. Plant growth regulators have many uses, depending on the variety and target plant. For example: controlling germination and dormancy; promoting rooting; promoting cell elongation and division; controlling lateral buds or tillers; controlling plant type (stunting and lodging prevention); controlling flowering or sex, inducing the fruit without seed; flower thinning and fruit thinning, and fruit dropping control; controlling the shape or maturity of the fruit; enhancing stress resistance (disease resistance, drought resistance, salt resistance, freezing resistance); enhancing the fertilizer absorption capacity; increasing sugar or changing acidity; improving fragrance and color; promoting secretion of latex or resin; defoliation or estimation (for mechanical harvesting); fresh keeping, etc. Some plant growth regulators are used at high concentrations as herbicides, while some herbicides also have growth regulating effects at low concentrations. The traditional plant growth regulator has high liquid medicine residue, large pollution and low utilization rate, and does not meet the development requirement of ecological agriculture.
WO2013/148339 reports a novel ABA agonist, quinabat, which binds to the PYR/PRL receptor protein and causes an abscisic acid response in vivo. Quinabactin has been shown to induce pore closure, inhibit water division and promote drought tolerance.
Disclosure of Invention
The invention aims to provide a plant growth regulator and a preparation method thereof, the preparation method is simple, the synthesis condition is mild, the yield is higher, the prepared compound has better effects of promoting plant growth, improving plant stress resistance and plant yield, and also has certain antibacterial and bacteriostatic properties, and due to the introduction of glycosyl, the compound is safer and more environment-friendly, and almost has no toxic and side effects.
The technical scheme of the invention is realized as follows:
the invention provides a plant growth regulator, which has a structure shown in a formula I:
formula I.
As a further improvement of the invention, agriculturally acceptable formulation adjuvants are also included.
The plant growth regulator generally comprises a formulation comprising from 0.01% to 99.99% by weight of a compound of the invention and from 0.01% to 99.909% by weight of a formulation adjuvant, preferably comprising from 0 to 25% by weight of a surfactant.
Preferably, the surfactant is selected from at least one of sodium dodecyl benzene sulfonate, calcium dodecyl benzene sulfonate, sodium tetradecyl sulfonate, sodium hexadecyl benzene sulfonate, sodium octadecyl sulfate, butylnaphthalene sulfonate, sodium di-isopropyl-naphthalene sulfonate and sodium tri-isopropyl-naphthalene sulfonate, sodium laureth-3-carboxylate, betaine, propionate and glycinate, lauryl dimethylamine oxide, lecithin.
The invention further provides a preparation method of the plant growth regulator, which comprises the following steps:
s1, reacting 2,3,4, 6-tetra-acetylated-beta-D-pyranyl isothiocyanate with 3-amino-1H-pyrazolo [3,4-b ] pyridine to prepare an intermediate A, wherein the structure of the intermediate A is as follows:
；
s2, reacting the intermediate A with benzoyl chloride to prepare an intermediate B, wherein the structure is as follows:
；
s3, reacting the intermediate B with sodium methoxide, and neutralizing with hydrochloric acid to obtain a product.
As a further improvement of the invention, the molar ratio of the 2,3,4, 6-tetra-acetylated-beta-D-pyranyl isothiocyanate to the 3-amino-1H-pyrazolo [3,4-b ] pyridine in the step S1 is 1:1-1.05, the solvent is toluene or xylene, and the temperature is heated to 90-100 ℃ for 2-4H.
As a further improvement of the invention, the molar ratio of the intermediate A to the benzoyl chloride in the step S2 is 1:1-1.1, the solvent is toluene or xylene, and the solvent is heated to 50-70 ℃ for 1-3h.
As a further improvement of the invention, the molar ratio of the intermediate B to sodium methoxide in the step S3 is 1:0.005-0.015, the solvent is a mixed solvent of methanol and dichloromethane, the volume ratio is 1-2:1, the reaction time is 20-30min, and then the reaction time is washed to be neutral by 10-15wt% of diluted hydrochloric acid.
The invention further provides a mixture comprising the above plant growth regulator and an additional active ingredient.
As a further improvement of the present invention, the active ingredient is at least one selected from the group consisting of indoleacetic acid, indolebutyric acid, brassinosteroids, jasmonic acid, and naphthylacetic acid.
The invention further provides a plant growth promoting composition which contains the plant growth regulator and indoleacetic acid, wherein the mass ratio of the plant growth regulator to the indoleacetic acid is 10-12:2-3.
The invention further provides application of the plant growth regulator in promoting plant growth, improving plant stress resistance and improving crop yield.
The compounds and compositions of the invention are generally applied at a rate of from 0.1g/ha to 1000g/ha, preferably from 5g/ha to 100 g/ha. For seed treatment, the application rate is typically between 0.0001g and 50g per 100kg seed.
The compounds and compositions of the present invention can be applied to dicotyledonous plants or monocotyledonous crops. The compounds and compositions of the present invention may be used in crops of useful plants, including perennial and annual crops.
The invention has the following beneficial effects: glucosides are widely present in plants, and many of them are biologically active and are responsible for important biological functions in the life of the plant. Some hormone substances for controlling plant growth exist in the form of glycoside, for example, cytokinin, namely active part of zeatin is zeatin glycoside, and compounds exist in the form of glycoside in gibberellin, so that glycoside compounds are widely used in agricultural production and have good plant growth regulating effect.
The novel glucoside compound is synthesized by the invention, the preparation method is simple, the synthesis condition is mild, the yield is higher, the prepared compound has better effects of promoting plant growth, improving plant stress resistance and improving plant yield, and also has certain antibacterial and bacteriostatic properties, and due to the introduction of glycosyl, the compound is safer and more environment-friendly, and almost has no toxic or side effect.
In addition, the novel glucoside compound and indoleacetic acid are compounded, have a synergistic effect, promote division and elongation of plant cells, promote growth and development of root systems and stems, regulate nutrition and metabolism of plants, improve resistance of the plants to stress, regulate ion transport and water balance in the plants, and promote growth and development of plant root systems. Promote the plant to produce anther and flower column, raise pollen yield and fertilization success rate of plant and raise seed yield. The two components are compounded and used in a proper proportion range, so that better promotion effect is achieved compared with single use, and the synergistic effect is achieved.
Drawings
In order to more clearly illustrate the embodiments of the invention or the technical solutions of the prior art, the drawings which are used in the description of the embodiments or the prior art will be briefly described, it being obvious that the drawings in the description below are only some embodiments of the invention, and that other drawings can be obtained according to these drawings without inventive faculty for a person skilled in the art.
FIG. 1 is a synthetic route diagram of a plant growth regulator of the present invention.
Detailed Description
The following description of the technical solutions in the embodiments of the present invention will be clear and complete, and it is obvious that the described embodiments are only some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Synthetic method reference for 2,3,4, 6-tetra-acetylated- β -D-pyran isothiocyanate: thisbe K L, christiffer K, solvent-free Preparation of Glycosyl Isothiocyanates [ J ]. Synthesis, 1995, 31:1228-1230.
Synthetic method reference for 1-bromo-2, 3,4, 6-tetra-acetylated- α -D-pyran glucose: brian S F, antonny J H, peter W G, et al 2,3,4, 6-Tetra-O-acetyl-alpha-D-glucopyranosyl Bromide [ M ]. New York: united States with John Wiley Inc. 1989:647-648.
Example 1:
the present example provides a plant growth regulator.
As shown in fig. 1, the preparation method is as follows:
s1, 0.1mol of 2,3,4, 6-tetra-acetylated-beta-D-pyranyl isothiocyanate and 0.1mol of 3-amino-1H-pyrazolo [3,4-b]Pyridine is dissolved in 200mL of toluene, heated to 90 ℃, stirred and reacted for 2 hours, cooled to room temperature, 200mL of water is added, separated, chloroform is added for extraction, the organic layers are combined, dried, filtered, the solvent is removed under reduced pressure, acetone and petroleum ether are used for recrystallization according to the volume ratio of 1:4, and the intermediate A is prepared with the yield of 91.2%. ESI-MS calculated: c (C) 21 H 26 N 5 O 9 S (m+h) + 524.14, found: 524.1.
nuclear magnetic results: 1 H NMR(300MHz，CDCl 3 )δ13.7（br，1H），8.60（d，J=6.2Hz，1H），7.76（d，J=5.7Hz，1H），7.37（dd，J=6.1Hz，5.7Hz，1H），5.25-5.32（m，2H），4.89（m，1H），4.78（d，1H），4.65（m，1H），4.32（d，2H），4.0（br，1H），2.02（m，13H）。
s2, dissolving 0.1mol of intermediate A and 0.1mol of benzoyl chloride in 150mL of toluene, heating to the temperature of 50 ℃, stirring and reacting for 1h, cooling to room temperature, adding 200mL of water, separating liquid, extracting with chloroform, combining organic layers, drying, filtering, removing the solvent under reduced pressure, and recrystallizing with diethyl ether and methanol according to the volume ratio of 1:5 to obtain an intermediate B with the yield of 94.5%. ESI-MS calculated: c (C) 28 H 30 N 5 O 10 S (m+h) + 628.16, found: 628.1.
nuclear magnetic results: 1 H NMR(300MHz，CDCl 3 )δ8.59（d，J=6.4Hz，1H），7.82（m，2H），7.76（d，J=5.4Hz，1H），7.38（dd，J=6.4Hz，5.5Hz，1H），7.54（m，1H），7.45（m，2H），5.25-5.32（m，2H），4.90（m，1H），4.77（d，1H），4.65（m，1H），4.32（d，2H），4.0（br，1H），2.02（m，13H）。
s3, dissolving 0.1mol of intermediate B in 100mL of a solvent, wherein the solvent is a mixed solvent of methanol and dichloromethane, the volume ratio is 1:1, dissolving 0.0005mol of sodium methoxide in 20mL of methanol, dropwise adding the solution into a reaction system, stirring at room temperature for reaction for 20min, washing with 10wt% of dilute hydrochloric acid to be neutral, removing the solvent under reduced pressure, and carrying out ethanol reaction: column chromatography of methylene dichloride (volume ratio 1:5) gives the product in 97.2% yield. ESI-MS calculated: c (C) 20 H 22 N 5 O 6 S (m+h) + 460.12, found: 460.1.
example 2:
the present example provides a plant growth regulator.
As shown in fig. 1, the preparation method is as follows:
s1, dissolving 0.1mol of 2,3,4, 6-tetra-acetylated-beta-D-pyranyl isothiocyanate and 0.105mol of 3-amino-1H-pyrazolo [3,4-b ] pyridine in 200mL of toluene, heating to 100 ℃, stirring for reaction for 4H, cooling to room temperature, adding 200mL of water, separating liquid, extracting with chloroform, combining organic layers, drying, filtering, removing solvent under reduced pressure, and recrystallizing with acetone and petroleum ether according to the volume ratio of 1:4 to obtain an intermediate A with the yield of 91.7 percent.
S2, dissolving 0.1mol of intermediate A and 0.11mol of benzoyl chloride in 150mL of toluene, heating to the temperature of 70 ℃, stirring and reacting for 3 hours, cooling to room temperature, adding 200mL of water, separating liquid, extracting with chloroform, combining organic layers, drying, filtering, removing the solvent under reduced pressure, and recrystallizing with diethyl ether and methanol according to the volume ratio of 1:5 to obtain an intermediate B, wherein the yield is 95.1%.
S3, dissolving 0.1mol of intermediate B in 100mL of a solvent, wherein the solvent is a mixed solvent of methanol and dichloromethane, the volume ratio is 1:1, dissolving 0.0015mol of sodium methoxide in 20mL of methanol, dropwise adding the solution into a reaction system, stirring at room temperature for reaction for 30min, washing 15wt% of dilute hydrochloric acid to be neutral, removing the solvent under reduced pressure, and carrying out ethanol reaction: column chromatography of methylene dichloride (volume ratio 1:5) gives the product with a yield of 98.4%.
Example 3:
the present example provides a plant growth regulator.
As shown in fig. 1, the preparation method is as follows:
s1, dissolving 0.1mol of 2,3,4, 6-tetra-acetylated-beta-D-pyranyl isothiocyanate and 0.102mol of 3-amino-1H-pyrazolo [3,4-b ] pyridine in 200mL of toluene, heating to the temperature of 95 ℃, stirring for reaction for 3H, cooling to the room temperature, adding 200mL of water, separating liquid, extracting with chloroform, combining organic layers, drying, filtering, removing the solvent under reduced pressure, and recrystallizing with acetone and petroleum ether according to the volume ratio of 1:4 to obtain an intermediate A with the yield of 92.1 percent.
S2, dissolving 0.1mol of intermediate A and 0.105mol of benzoyl chloride in 150mL of toluene, heating to the temperature of 60 ℃, stirring and reacting for 2 hours, cooling to room temperature, adding 200mL of water, separating liquid, extracting with chloroform, combining organic layers, drying, filtering, removing the solvent under reduced pressure, and recrystallizing with diethyl ether and methanol according to the volume ratio of 1:5 to obtain an intermediate B, wherein the yield is 95.3%.
S3, dissolving 0.1mol of intermediate B in 100mL of a solvent, wherein the solvent is a mixed solvent of methanol and dichloromethane, the volume ratio is 1:1, dissolving 0.001mol of sodium methoxide in 20mL of methanol, dropwise adding the solution into a reaction system, stirring at room temperature for reaction for 25min, washing the solution to neutrality by 12wt% of dilute hydrochloric acid, removing the solvent under reduced pressure, and carrying out ethanol reaction: column chromatography of methylene dichloride (volume ratio 1:5) gives the product with a yield of 98.2%.
Example 4:
the present example provides a plant growth promoting composition comprising the plant growth regulator prepared in example 3 and indoleacetic acid in a mass ratio of 10:2.
Example 5:
the present example provides a plant growth promoting composition comprising the plant growth regulator prepared in example 3 and indoleacetic acid in a mass ratio of 12:3.
Example 6:
the present example provides a plant growth promoting composition comprising the plant growth regulator prepared in example 3 and indoleacetic acid in a mass ratio of 11:2.5.
Example 7:
the present example provides a plant growth promoting composition comprising the plant growth regulator prepared in example 3 and indoleacetic acid in a mass ratio of 2:10.
Example 8:
the present example provides a plant growth promoting composition comprising the plant growth regulator prepared in example 3 and indoleacetic acid in a mass ratio of 20:2.5.
Test example 1 bud initiation test
The compounds or compositions of examples 3-8 were diluted to 5wt% suspension, 5wt% indoleacetic acid suspension, 5wt% cytokinin suspension, and each diluted with distilled water to a treatment solution at a concentration of 20. Mu.g/mL. Clear water was used as a control.
Selecting wheat seeds with uniform and full grain size, sterilizing the seeds by hydrogen peroxide, soaking the seeds in the diluent in a beaker for culturing for 24 hours, treating 100 grains of the seeds in each group, repeating for 3 times, uniformly placing the seeds in a culture dish with double-layer filter paper after the treatment, keeping a certain distance between the seeds, placing the seeds after placing the seeds, preserving heat at 25 ℃ for germination acceleration treatment, spraying distilled water at regular time, keeping the filter paper moist, and keeping the germination conditions of each group.
The germination percentage of wheat seeds in each group was counted after 24 hours with the length of the embryo being about 1/2 of the length of the seeds as a standard, and the germination promotion percentage of each group was calculated, and the results are shown in Table 1.
Germination acceleration (%) = (average germination rate of treated group-average germination rate of control group)/average germination rate of control group x 100%.
TABLE 1
。
From the above table, it can be concluded that the plant growth regulator shown in formula I prepared in example 3 of the present invention has better germination promoting effect, and the compositions in examples 4-6 have better germination promoting effect, and the compositions obtained in the ratio range of the suitable compound and indoleacetic acid have better germination promoting effect, and the two have synergistic effect.
Test example 2 rooting-promoting test
The compounds or compositions of examples 3-8 were diluted to 5wt% suspension, 5wt% indoleacetic acid suspension, 5wt% cytokinin suspension, and each diluted with distilled water to a treatment solution at a concentration of 30. Mu.g/mL. The clear water treatment was used as a control.
Selecting wheat seeds with uniform and full grain size, sterilizing the seeds by hydrogen peroxide, soaking the seeds in the diluent in a beaker for culturing for 8 hours, carrying out repeated treatment for 3 times on 15 wheat grains, uniformly placing the seeds on a wet paper bed, keeping a distance between the seeds, placing embryo parts upwards and towards the same side when placing the seeds, carrying out germination accelerating treatment for 24 hours at 25 ℃ after placing the seeds, and regularly spraying distilled water to keep the paper bed moist. After the main root of wheat is exposed for about 2mm, the main root of wheat is planted in a solid culture medium and then is cultured under constant temperature and humidity. After 40h, main root, lateral root and stem heights were measured. The promotion rate is calculated.
Promotion (%) = (treatment group average length-control group average length)/control group average length×100%.
The results are shown in Table 2.
TABLE 2
。
As shown in the table above, the plant growth regulator shown in the formula I prepared in the embodiment 3 of the invention has better rooting promoting effect, and meanwhile, the compositions in the embodiments 4-6 have better rooting promoting effect and are obviously better than those in the control group.
Test example 3 peanut yield test
The compounds or compositions of examples 3-8 were diluted to 5wt% suspension, 5wt% indoleacetic acid suspension, 5wt% cytokinin suspension, and distilled water to 20mg/L treatment solutions, respectively. The clear water treatment was used as a control.
The number of the seedling protecting plants for hectare is 18-20 ten thousand, and the management mode is consistent with that of a field. The 2-year test is carried out on the leaf surfaces of the peanuts in the early flowering stage in sunny windless weather, and the spraying amount is 10L/mu. Area per cell is 16.25 m 2 Treatments and controls were each set 3 replicates. And continuously spraying 21d. The number of fruits per kg was calculated, the kernel yield and the yield increase (relative to the control group).
The results are shown in Table 3.
TABLE 3 Table 3
。
As shown in the table, the plant growth regulator shown in the formula I prepared in the embodiment 3 of the invention has better yield increasing effect, and meanwhile, the compositions in the embodiment 4-6 have better yield increasing effect, which is obviously better than that of single indoleacetic acid or cytokinin.
Test example 4 bactericidal activity test
10mg of the compound of example 3 was dissolved in 10mL of an appropriate amount of N, N-dimethylformamide, and then 5wt% of an aqueous solution of Tween-80 emulsifier was added to dilute to 5mg/L, 10mg/L, 20mg/L, 40mg/L, and the group without drug was used as a blank group. By adopting an in-vitro plate method, the pathogen to be tested comprises mango ashMould germBotrytis cinerea) Watermelon anthracnose pathogenColletotrichum orbiculare) Apple rot pathogenBotryosphaeria dothidea) Large spot germ of riceCochliobolus miyabeanus) Wheat gibberella germFusarium graminearum）。
The testing method comprises the following steps: according to the pesticide laboratory biological assay experiment rule, an in vitro plate method is adopted, 1mL of liquid medicine is sucked under the aseptic condition and added into a culture dish, 9mL of PDA culture medium is added, and the mixture is uniformly shaken to prepare a medicine-containing plate. Cutting fungus disk along the outer edge of mycelium with a puncher with diameter of 2mm, transferring onto a medicated plate, repeating each group for 3 times, maintaining constant temperature at 25+ -1deg.C, maintaining constant humidity at 70+ -5%, and maintaining constant humidity at 5+ -0.5% CO 2 Culturing for 48 hours under the condition, measuring the average bacterial disc expansion diameter, and calculating the control effect.
Control (%) = (colony diameter of blank group-colony diameter of treatment group)/(colony diameter of blank group-2) ×100%.
The test results are shown in Table 4.
TABLE 4 Table 4
。
As is clear from the above table, the compound in example 3 of the present invention has a certain bactericidal activity.
The foregoing description of the preferred embodiments of the invention is not intended to be limiting, but rather is intended to cover all modifications, equivalents, alternatives, and improvements that fall within the spirit and scope of the invention.
Claims (10)
1. A plant growth regulator compound characterized by having the structure of formula I:
formula I.
2. A plant growth regulator is characterized by comprising a structural compound shown in a formula I and an agricultural chemicalAcceptable formulation adjuvants;formula I.
3. A method of preparing a plant growth regulator compound according to claim 1, comprising the steps of:
s1, reacting 2,3,4, 6-tetra-acetylated-beta-D-pyranyl isothiocyanate with 3-amino-1H-pyrazolo [3,4-b ] pyridine to prepare an intermediate A, wherein the structure of the intermediate A is as follows:
；
s2, reacting the intermediate A with benzoyl chloride to prepare an intermediate B, wherein the structure is as follows:
；
s3, reacting the intermediate B with sodium methoxide, and neutralizing with hydrochloric acid to obtain a product.
4. The process according to claim 3, wherein the molar ratio of 2,3,4, 6-tetra-acetylated-. Beta. -D-pyran isothiocyanate to 3-amino-1H-pyrazolo [3,4-b ] pyridine in step S1 is 1:1-1.05, the solvent is toluene or xylene, and the mixture is heated to a temperature of 90-100℃for a period of 2-4 hours.
5. The process according to claim 3, wherein the molar ratio of intermediate A to benzoyl chloride in step S2 is 1:1-1.1, the solvent is toluene or xylene, and the mixture is heated to 50-70 ℃ for 1-3 hours.
6. The preparation method according to claim 3, wherein in the step S3, the molar ratio of the intermediate B to the sodium methoxide is 1:0.005-0.015, the solvent is a mixed solvent of methanol and dichloromethane, the volume ratio is 1-2:1, the reaction time is 20-30min, and then the mixture is washed to be neutral by 10-15wt% of diluted hydrochloric acid.
7. A mixture comprising the plant growth regulator compound of claim 1 and an additional active ingredient.
8. The mixture according to claim 7, wherein the active ingredient is selected from at least one of indoleacetic acid, indolebutyric acid, brassinosteroids, jasmonic acid, and naphthylacetic acid.
9. A plant growth promoting composition comprising the plant growth regulator compound of claim 1 and indoleacetic acid in a mass ratio of 10-12:2-3.
10. Use of the plant growth regulator compound according to claim 1 or the plant growth regulator according to claim 2 for promoting germination of wheat seeds, rooting of wheat seeds, and yield increase of peanuts.
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| CN103709158A (en) * | 2013-12-26 | 2014-04-09 | 青岛科技大学 | Pyrazolopyrimidine ureas compound and application thereof |
| CN110483605A (en) * | 2019-08-16 | 2019-11-22 | 郑州信联生化科技有限公司 | The preparation and its application of one plant growth regulators |
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