CN108997235A - A kind of high-dissolvability plant growth regulator and preparation method thereof - Google Patents
A kind of high-dissolvability plant growth regulator and preparation method thereof Download PDFInfo
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- CN108997235A CN108997235A CN201810713770.9A CN201810713770A CN108997235A CN 108997235 A CN108997235 A CN 108997235A CN 201810713770 A CN201810713770 A CN 201810713770A CN 108997235 A CN108997235 A CN 108997235A
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- paclobutrazol
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- eutectic
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
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- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
Abstract
The invention discloses a kind of high-dissolvability plant growth regulator and preparation method thereof, a kind of high-dissolvability plant growth regulator is paclobutrazol nicotinamide eutectic, the paclobutrazol nicotinamide eutectic is monoclinic system, its axial length is a=7.2318, b=11.3571 and c=16.1134, shaft angle α=γ=90 ° and β=105 ° have the advantages that improve solubility.
Description
Technical field
The present invention relates to a kind of high-dissolvability plant growth regulator and preparation method thereof.
Background technique
The chemical name of paclobutrazol (Propiconazole) is (2RS, 3RS) -1- (4- chlorphenyl) -4,4- dimethyl -2-
(1H-1,2,4- triazol-1-yls) amyl- 3- alcohol, is triazole type plant growth regulator, is the inhibition of endogenous gibberellins synthesis
Agent has and delays plant growth, inhibits stem elongation, shortens internode, promote plant tillering, promote bud differentiation, increases plant
Anti-adversity improves yield and other effects.This product is suitable for rice, wheat, peanut, fruit tree, tobacco, rape, soybean, flowers, grass
(plant) object is made on level ground etc., and using effect is significant.
The study found that solubility of the paclobutrazol in 25 DEG C of water is lower than 0.01mg/ml, it is not easily dissolved when spraying,
Partly precipitated not only wastes drug and the content for being pre-designed and using also is not achieved, cause containing for dissolved paclobutrazol at the bottom
Measure standard not up to standard.
Summary of the invention
The first object of the present invention is to provide a kind of high-dissolvability plant growth regulator, has and improves the excellent of solubility
Point.
Above-mentioned technical purpose of the invention has the technical scheme that
A kind of high-dissolvability plant growth regulator, is paclobutrazol nicotinamide eutectic, and the paclobutrazol nicotinamide eutectic is
Monoclinic system, axial length areAnd c=16.1134, shaft angle α=γ=90 ° and β=105 °.
Further preferably are as follows: radiated using Cu-K α, the X-ray powder that the paclobutrazol nicotinamide eutectic is indicated with 2 θ angles
Last diffraction pattern has a following characteristics peak: 7.4 ± 0.2 °, 11.5 ± 0.2 °, 15.1 ± 0.2 °, 17.5 ± 0.2 ° and 23.4 ±
0.2°。
Further preferably are as follows: the X-ray powder diffraction figure that the paclobutrazol nicotinamide eutectic is indicated with 2 θ angles have with
Lower characteristic peak: 7.4 ± 0.2 °, 11.5 ± 0.2 °, 15.1 ± 0.2 °, 15.8 ± 0.2 °, 17.5 ± 0.2 °, 20.8 ± 0.2 °,
21.7 ± 0.2 °, 23.4 ± 0.2 ° and 25.1 ± 0.2 °.
Further preferably are as follows: the X-ray powder diffraction figure that the paclobutrazol nicotinamide eutectic is indicated with 2 θ angles have with
Lower characteristic peak: 7.4 ± 0.2 °, 8.4 ± 0.2 °, 11.5 ± 0.2 °, 15.1 ± 0.2 °, 15.8 ± 0.2 °, 17.5 ± 0.2 °, 20.8
± 0.2 °, 21.7 ± 0.2 °, 23.4 ± 0.2 °, 25.1 ± 0.2 ° and 31.3 ± 0.2 °.
Further preferably are as follows: the X-ray powder diffraction figure that the paclobutrazol nicotinamide eutectic is indicated with 2 θ angles have with
Lower characteristic peak and its relative intensity:
Further preferably are as follows: in the paclobutrazol nicotinamide eutectic, the molar ratio of paclobutrazol and niacinamide is 1: 1.
Further preferably are as follows: solubility of the paclobutrazol nicotinamide eutectic in 25 DEG C is 8~10mg/mL.
The second object of the present invention is to provide a kind of preparation method of high-dissolvability plant growth regulator.
Above-mentioned technical purpose of the invention has the technical scheme that
A kind of preparation method of high-dissolvability plant growth regulator, comprising the following steps:
(1) formation of paclobutrazol solution: taking paclobutrazol, and organic solvent is added, and ultrasonic dissolution obtains paclobutrazol solution；It presses
The amount ratio of quality meter, paclobutrazol and organic solvent is 1: 4~5；Organic solvent selects acetonitrile or acetone；
(2) formation of nicotinamide soln: taking niacinamide, and water is added, and ultrasonic disperse obtains nicotinoyl amine aqueous solution；By quality
The amount ratio of meter, niacinamide and water is 1: 12~15；
(3) formation of paclobutrazol nicotinamide eutectic: nicotinoyl amine aqueous solution being added dropwise into paclobutrazol solution, and stirring is anti-at room temperature
It answers, solid is first precipitated and is redissolved, filters to take filtrate after reacting 1.5~2hr, filtrate and ether is mixed to get mixed liquor, mixes
Solvent is evaporated off in 40~45 DEG C of backspins in liquid, obtains paclobutrazol nicotinamide eutectic；By mol, the amount ratio of paclobutrazol and niacinamide
It is 1.0~1.2: 1；By volume, filtrate and ether mixing ratio are 1: 1.5~2.0.
In conclusion the invention has the following advantages:
In 25 DEG C of water, the solubility of paclobutrazol is < 0.01mg/ml, and the solubility of paclobutrazol nicotinamide eutectic is
9.0mg/ml, solubility of the paclobutrazol nicotinamide eutectic in 25 DEG C of water are apparently higher than the solubility of paclobutrazol；Paclobutrazol nicotinoyl
Crystal form and purity of the amine eutectic at 0 DEG C/30%RH, 25 DEG C/60%RH and 40 DEG C/75%RH after placement for a long time keep steady
It is fixed, there is preferable stability；The aqueous solution of the paclobutrazol nicotinamide eutectic of various concentration is in 25 DEG C/60%RH and 40
DEG C/75%RH under for a long time place after solubility and purity keep stable, have preferable stability of solution；
Paclobutrazol can be applied by way of paclobutrazol nicotinamide eutectic, be able to maintain in preparation, crop and soil
Stable high-dissolvability value reduces a possibility that paclobutrazol is dissolved in the formulation but is precipitated in soil or crop, efficacy stability
Controllably.
Detailed description of the invention
Fig. 1 is the XRPD map of the paclobutrazol nicotinamide eutectic of the application；
Fig. 2 is the XRPD map of paclobutrazol.
Specific embodiment
Below in conjunction with attached drawing, invention is further described in detail.
This specific embodiment is only explanation of the invention, is not limitation of the present invention, those skilled in the art
Member can according to need the modification that not creative contribution is made to the present embodiment after reading this specification, but as long as at this
All by the protection of Patent Law in the protection scope of invention.
Detecting instrument and method:
Instrument used in X-ray powder diffraction (XPRD) is Bruker D8Advance diffractometer, is adopted
The K α X-ray for being 1.54nm with copper target wavelength, under the operating condition of 40kV and 40mA, θ -2 θ angular instrument, Mo monochromator,
Lynxeye detector.Instrument was detected using preceding with diamond dust.Acquisition software is Diffrac Plus XRD
Commander.Sample is tested at room temperature, and the sample that needs are detected is placed on phosphatization silicon on piece.Detailed testing conditions are such as
Under, angular range: 3-40 ° of 2 θ, step-length: 0.02 ° of 2 θ, speed: 0.2s. step -1.Unless stated otherwise, sample before detection without
Grinding.
Embodiment 1: a kind of high-dissolvability plant growth regulator is prepared by the following method:
(1) formation of paclobutrazol solution: taking paclobutrazol, and acetonitrile is added, and ultrasonic dissolution obtains paclobutrazol solution；By quality
The amount ratio of meter, paclobutrazol and acetonitrile is 1: 4；
(2) formation of nicotinamide soln: taking niacinamide, and water is added, and ultrasonic disperse obtains nicotinoyl amine aqueous solution；By quality
The amount ratio of meter, niacinamide and water is 1: 12；
(3) formation of paclobutrazol nicotinamide eutectic: nicotinoyl amine aqueous solution being added dropwise into paclobutrazol solution, and stirring is anti-at room temperature
Answer, solid be first precipitated and is redissolved, filters to take filtrate after reacting 1.5r, filtrate and ether are mixed to get mixed liquor, mixed liquor in
Solvent is evaporated off in 40 DEG C of backspins, obtains paclobutrazol nicotinamide eutectic；By mol, the amount ratio of paclobutrazol and niacinamide is 1.0: 1；
By volume, filtrate and ether mixing ratio are 1: 1.5.
Embodiment 2: a kind of high-dissolvability plant growth regulator is prepared by the following method:
(1) formation of paclobutrazol solution: taking paclobutrazol, and acetone is added, and ultrasonic dissolution obtains paclobutrazol solution；By quality
The amount ratio of meter, paclobutrazol and acetone is 1: 5；
(2) formation of nicotinamide soln: taking niacinamide, and water is added, and ultrasonic disperse obtains nicotinoyl amine aqueous solution；By quality
The amount ratio of meter, niacinamide and water is 1: 15；
(3) formation of paclobutrazol nicotinamide eutectic: nicotinoyl amine aqueous solution being added dropwise into paclobutrazol solution, and stirring is anti-at room temperature
It answers, solid is first precipitated and is redissolved, filters to take filtrate after reacting 2hr, filtrate and ether is mixed to get mixed liquor, mixed liquor is in 45
Solvent is evaporated off in DEG C backspin, obtains paclobutrazol nicotinamide eutectic；By mol, the amount ratio of paclobutrazol and niacinamide is 1.2: 1；It presses
Stereometer, filtrate and ether mixing ratio are 1: 2.0.
Performance characterization
1, the XRPD map of paclobutrazol nicotinamide eutectic (has obvious area with stable crystal form Fig. 2 of paclobutrazol as shown in Figure 1
Not), it is monoclinic system that simulation, which calculates discovery paclobutrazol nicotinamide eutectic, and axial length isAnd c=
16.1134, shaft angle α=γ=90 ° and β=105 °.
2, nuclear-magnetism test is found, in paclobutrazol nicotinamide eutectic, the molar ratio of paclobutrazol and niacinamide is 1: 1.
3, solubility test: being put into 100mg sample in reaction flask, is gradually added into 25 DEG C of water, each additive amount point
Not Wei 25 μ l, 25 μ l, 50 μ l, 100 μ l, 200 μ l... (summation that additive amount is front additive amount), every time add rear plug on bottle
Plug is placed in ultrasound 5min at 25 DEG C, until sample is completely dissolved.Parallel testing 5 times.Test result is as shown in table 1.Table 1 is aobvious
Show, in 25 DEG C of water, the solubility of paclobutrazol is < 0.01mg/ml, and the solubility of paclobutrazol nicotinamide eutectic is 9.0mg/
Ml, solubility of the paclobutrazol nicotinamide eutectic in 25 DEG C of water are apparently higher than the solubility of paclobutrazol.
1 solubility test of table
4, stability is tested
100mg sample is respectively put into multiple vials, opening is placed in 0 DEG C/30%RH, 25 DEG C/60%RH respectively
With place 30 days and 180 days under 40 DEG C/75%RH, the crystal form (XRPD) and purity (gas-chromatography of sample after test is placed respectively
Mass spectrometer combination analysis).It parallel test 5 times, is averaged.Test result is as shown in table 2.Table 2 shows, paclobutrazol and more
Imitate the crystal form after azoles nicotinamide eutectic is placed 30 days and 180 days at 0 DEG C/30%RH, 25 DEG C/60%RH and 40 DEG C/75%RH
It keeps stable with purity, there is preferable stability.
The test of 2 stability of table
5, stability of solution is tested
0.5,2.0 and 8.0mg sample/ml aqueous solution is prepared respectively, is respectively placed in closed vial, is placed respectively
Observed whether it has solid precipitation, the purity (gas of test sample in 25 DEG C/60%RH and 40 DEG C/75%RH lower 10 days and 60 days
Phase chromatograph-mass spectrometer combination analysis).It parallel test 5 times, is averaged.Test result is as shown in table 3.The display of table 3, multiple-effect
The aqueous solution of azoles nicotinamide eutectic placed 10 days and 60 days at 25 DEG C/60%RH and 40 DEG C/75%RH after solubility and pure
Degree keeps stablizing, and has preferable stability.
The test of 3 stability of solution of table
The specific implementation of the invention is not to be limited to these illustrations for the above content, and technology belonging to the present invention is led
For the those of ordinary skill in domain, without departing from the inventive concept of the premise, a number of simple deductions or replacements can also be made,
It all shall be regarded as belonging to present invention scope of patent protection determined by the appended claims.
Claims (8)
1. a kind of high-dissolvability plant growth regulator, which is characterized in that be paclobutrazol nicotinamide eutectic, the paclobutrazol nicotinoyl
Amine eutectic is monoclinic system, and axial length isAnd c=16.1134, shaft angle α=γ=90 ° and β
=105 °.
2. a kind of high-dissolvability plant growth regulator according to claim 1, which is characterized in that it is radiated using Cu-K α,
The X-ray powder diffraction figure that the paclobutrazol nicotinamide eutectic is indicated with 2 θ angles is with following characteristics peak: 7.4 ± 0.2 °,
11.5 ± 0.2 °, 15.1 ± 0.2 °, 17.5 ± 0.2 ° and 23.4 ± 0.2 °.
3. a kind of high-dissolvability plant growth regulator according to claim 2, which is characterized in that the paclobutrazol nicotinoyl
Amine eutectic has following characteristics peak: 7.4 ± 0.2 °, 11.5 ± 0.2 °, 15.1 with the X-ray powder diffraction figure that 2 θ angles indicate
± 0.2 °, 15.8 ± 0.2 °, 17.5 ± 0.2 °, 20.8 ± 0.2 °, 21.7 ± 0.2 °, 23.4 ± 0.2 ° and 25.1 ± 0.2 °.
4. a kind of high-dissolvability plant growth regulator according to claim 3, which is characterized in that the paclobutrazol nicotinoyl
The X-ray powder diffraction figure that amine eutectic is indicated with 2 θ angles has a following characteristics peak: 7.4 ± 0.2 °, 8.4 ± 0.2 °, 11.5 ±
0.2°、15.1±0.2°、15.8±0.2°、17.5±0.2°、20.8±0.2°、21.7±0.2°、23.4±0.2°、25.1±
0.2 ° and 31.3 ± 0.2 °.
5. a kind of high-dissolvability plant growth regulator according to claim 4, which is characterized in that the paclobutrazol nicotinoyl
Amine eutectic has following characteristics peak and its relative intensity with the X-ray powder diffraction figure that 2 θ angles indicate:
6. a kind of high-dissolvability plant growth regulator according to claim 5, which is characterized in that the paclobutrazol nicotinoyl
In amine eutectic, the molar ratio of paclobutrazol and niacinamide is 1: 1.
7. a kind of high-dissolvability plant growth regulator according to claim 6, which is characterized in that the paclobutrazol nicotinoyl
Solubility of the amine eutectic in 25 DEG C is 8~10mg/mL.
8. such as a kind of described in any item preparation methods of high-dissolvability plant growth regulator of claim 1-7, feature exists
In, comprising the following steps:
(1) formation of paclobutrazol solution: taking paclobutrazol, and organic solvent is added, and ultrasonic dissolution obtains paclobutrazol solution；By quality
The amount ratio of meter, paclobutrazol and organic solvent is 1: 4~5；Organic solvent selects acetonitrile or acetone；
(2) formation of nicotinamide soln: taking niacinamide, and water is added, and ultrasonic disperse obtains nicotinoyl amine aqueous solution；By mass, cigarette
The amount ratio of amide and water is 1: 12~15；
(3) formation of paclobutrazol nicotinamide eutectic: nicotinoyl amine aqueous solution being added dropwise into paclobutrazol solution, is stirred to react at room temperature,
Solid is first precipitated to be redissolved, filters to take filtrate after reacting 1.5~2hr, filtrate and ether are mixed to get mixed liquor, mixed liquor in
Solvent is evaporated off in 40~45 DEG C of backspins, obtains paclobutrazol nicotinamide eutectic；By mol, the amount ratio of paclobutrazol and niacinamide is
1.0~1.2: 1；By volume, filtrate and ether mixing ratio are 1: 1.5~2.0.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2041927A (en) * | 1979-02-09 | 1980-09-17 | Ici Ltd | Enantiomers of triazole compounds |
| CN101679389A (en) * | 2007-03-23 | 2010-03-24 | 先正达有限公司 | co-crystals of propiconazole |
| WO2014023682A1 (en) * | 2012-08-06 | 2014-02-13 | Basf Se | Multicomponent crystalline system comprising deferasirox and isonicotinamide and a process for the preparation thereof |
| CN105828614A (en) * | 2013-12-19 | 2016-08-03 | 日本曹达株式会社 | Co-crystal production method |
| WO2018085932A1 (en) * | 2016-11-10 | 2018-05-17 | Apotex Inc. | Novel crystalline forms of lesinurad |
-
2018
- 2018-07-01 CN CN201810713770.9A patent/CN108997235A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2041927A (en) * | 1979-02-09 | 1980-09-17 | Ici Ltd | Enantiomers of triazole compounds |
| CN101679389A (en) * | 2007-03-23 | 2010-03-24 | 先正达有限公司 | co-crystals of propiconazole |
| WO2014023682A1 (en) * | 2012-08-06 | 2014-02-13 | Basf Se | Multicomponent crystalline system comprising deferasirox and isonicotinamide and a process for the preparation thereof |
| CN105828614A (en) * | 2013-12-19 | 2016-08-03 | 日本曹达株式会社 | Co-crystal production method |
| WO2018085932A1 (en) * | 2016-11-10 | 2018-05-17 | Apotex Inc. | Novel crystalline forms of lesinurad |
Non-Patent Citations (6)
| Title |
|---|
| JIAO CHEN等: "Solubility modelling and preferential solvation of paclobutrazol in co-solvent mixtures of (ethanol, n-propanol and 1,4-dioxane) + water", 《THE JOURNAL OF CHEMICAL THERMODYNAMICS》 * |
| XINBAO LI等: "Solubility determination and thermodynamic modeling of paclobutrazol in nine organic solvents from T = (278.15 to 318.15) K and mixing properties of solutions", 《THE JOURNAL OF CHEMICAL THERMODYNAMICS》 * |
| 周学良等: "《精细化学品大全 农药卷》", 31 December 2000, 浙江科学技术出版社 * |
| 孙晓伟: "药物共晶热力学相图及溶解行为研究", 《天津大学硕士学位论文》 * |
| 张瑶: "三唑类杀菌剂金属配合物的合成，表征，生物活性及缓释性能研究", 《西北大学硕士学位论文》 * |
| 施洪龙等: "《X射线粉末衍射和电子衍射 常用实验技术与数据分析》", 31 July 2014, 中央民族大学出版社 * |
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Application publication date: 20181214 |