CN108689953A - A method of improving triazole type plant growth regulator paclobutrazol solubility - Google Patents
A method of improving triazole type plant growth regulator paclobutrazol solubility Download PDFInfo
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- CN108689953A CN108689953A CN201810705208.1A CN201810705208A CN108689953A CN 108689953 A CN108689953 A CN 108689953A CN 201810705208 A CN201810705208 A CN 201810705208A CN 108689953 A CN108689953 A CN 108689953A
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- paclobutrazol
- benzoic acid
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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
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
- C07D249/12—Oxygen or sulfur atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/04—Monocyclic monocarboxylic acids
- C07C63/06—Benzoic acid
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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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Abstract
The invention discloses a kind of methods improving triazole type plant growth regulator paclobutrazol solubility, this method is that paclobutrazol is prepared into paclobutrazol benzoic acid eutectic, the paclobutrazol benzoic acid eutectic is monoclinic system, its axial length is a=6.1734, b=12.3459 and c=15.2132, shaft angle α=γ=90 ° and β=100 ° have the advantages that improve solubility.
Description
Technical field
The present invention relates to a kind of methods improving triazole type plant growth regulator paclobutrazol solubility.
Background technology
The chemical name of paclobutrazol (Propiconazole) is (2RS, 3RS) -1- (4- chlorphenyls) -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 cane 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 notable.
The study found that solubility of the paclobutrazol in 25 DEG C of water is less 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
Amount standard not up to standard.
Invention content
The object of the present invention is to provide a kind of methods improving triazole type plant growth regulator paclobutrazol solubility, have
The advantages of improving solubility.
The present invention above-mentioned technical purpose technical scheme is that:
A method of triazole type plant growth regulator paclobutrazol solubility is improved, paclobutrazol is prepared into paclobutrazol benzene
Formic acid eutectic, the paclobutrazol benzoic acid eutectic are monoclinic system, and axial length is And c=
15.2132, shaft angle α=γ=90 ° and β=100 °.
Further preferably:It is radiated using Cu-K α, the X-ray powder that the paclobutrazol benzoic acid eutectic is indicated with 2 θ angles
Last diffraction pattern has following characteristics peak:5.3 ± 0.2 °, 5.7 ± 0.2 °, 7.7 ± 0.2 °, 14.2 ± 0.2 ° and 24.0 ± 0.2 °.
Further preferably:The X-ray powder diffraction figure that the paclobutrazol benzoic acid eutectic is indicated with 2 θ angles have with
Lower characteristic peak:4.6±0.2°,5.3±0.2°,5.7±0.2°,7.7±0.2°,9.5±0.2°,10.0±0.2°,14.2±
0.2 °, 18.0 ± 0.2 ° and 24.0 ± 0.2 °.
Further preferably:The X-ray powder diffraction figure that the paclobutrazol benzoic acid eutectic is indicated with 2 θ angles have with
Lower characteristic peak:4.6±0.2°,5.3±0.2°,5.7±0.2°,6.4±0.2°,7.7±0.2°,9.5±0.2°,10.0±
0.2 °, 14.2 ± 0.2 °, 18.0 ± 0.2 °, 24.0 ± 0.2 °, 27.2 ± 0.2 ° and 33.3 ± 0.2 °.
Further preferably:The X-ray powder diffraction figure that the paclobutrazol benzoic acid eutectic is indicated with 2 θ angles have with
Lower characteristic peak and its relative intensity:
Further preferably:In the paclobutrazol benzoic acid eutectic, the molar ratio of paclobutrazol and benzoic acid is 1: 1.
Further preferably:Solubility of the paclobutrazol benzoic acid eutectic in 25 DEG C of water is 10~15mg/mL.
Further preferably:The paclobutrazol benzoic acid eutectic is prepared by the following method:
(1) formation of paclobutrazol solution:Paclobutrazol is taken, organic solvent is added, ultrasonic dissolution obtains paclobutrazol solution;It presses
The amount ratio of quality meter, paclobutrazol and organic solvent is 1: 3~5;Organic solvent selects isopropanol or normal propyl alcohol;
(2) formation of benzoic acid solution:Benzoic acid is taken, water is added, ultrasonic disperse obtains benzoic acid aqueous solution;By quality
The amount ratio of meter, benzoic acid and water is 1: 8~10;
(3) formation of paclobutrazol benzoic acid eutectic:Benzoic acid aqueous solution is added dropwise into paclobutrazol solution, 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 ethyl alcohol is mixed to get mixed liquor, mixes
Solvent is evaporated off in 40~45 DEG C of backspins in liquid, obtains paclobutrazol benzoic acid eutectic;By mol, the amount ratio of paclobutrazol and benzoic acid
It is 1.0~1.2: 1;By volume, filtrate and ethyl alcohol mixing ratio are 1: 2.5~3.0.
In conclusion the invention has the advantages that:
In 25 DEG C of water, the solubility of paclobutrazol is < 0.01mg/ml, and the solubility of paclobutrazol benzoic acid eutectic is
13.5mg/ml, solubility of the paclobutrazol benzoic acid eutectic in 25 DEG C of water are apparently higher than the solubility of paclobutrazol;Paclobutrazol benzene first
Crystal form and purity of the sour 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 benzoic acid 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 the form of paclobutrazol benzoic acid eutectic, can be kept in preparation, crop and soil
Stable high-dissolvability value reduces the possibility that paclobutrazol is dissolved but is precipitated in soil or crop in the formulation, efficacy stability
Controllably.
Description of the drawings
Fig. 1 is the XRPD collection of illustrative plates of the paclobutrazol benzoic acid eutectic of the application;
Fig. 2 is the XRPD collection of illustrative plates of paclobutrazol.
Specific implementation mode
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, people in the art
Member can as needed make the present embodiment the modification of not creative contribution after reading this specification, but as long as at this
It is all protected by Patent Law in the protection domain of invention.
Detecting instrument and method:
Instrument used in X-ray powder diffraction (XPRD) is Bruker D8Advance diffractometer, is adopted
The K α X-rays for being 1.54nm with copper target wavelength, under the operating condition of 40kV and 40mA, θ -2 θ angular instruments, Mo monochromators,
Lynxeye detectors.Instrument was detected using preceding with diamond dust.Acquisition software is Diffrac Plus XRD
Commander.Sample is tested at ambient temperature, and the sample that needs detect 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. steps -1.Unless stated otherwise, sample before detection without
Grinding.
Embodiment 1:A kind of paclobutrazol benzoic acid eutectic, is prepared by the following method:
(1) formation of paclobutrazol solution:Paclobutrazol is taken, isopropanol is added, ultrasonic dissolution obtains paclobutrazol solution;By matter
The amount ratio of gauge, paclobutrazol and isopropanol is 1: 3;
(2) formation of benzoic acid solution:Benzoic acid is taken, water is added, ultrasonic disperse obtains benzoic acid aqueous solution;By quality
The amount ratio of meter, benzoic acid and water is 1: 8;
(3) formation of paclobutrazol benzoic acid eutectic:Benzoic acid aqueous solution is added dropwise into paclobutrazol solution, stirring is anti-at room temperature
Answer, solid be first precipitated and is redissolved, filtrate is filtered to take after reacting 1.5hr, filtrate and ethyl alcohol are mixed to get mixed liquor, mixed liquor in
Solvent is evaporated off in 40 DEG C of backspins, obtains paclobutrazol benzoic acid eutectic;By mol, the amount ratio of paclobutrazol and benzoic acid is 1.0: 1;
By volume, filtrate and ethyl alcohol mixing ratio are 1: 2.5.
Embodiment 2:A kind of paclobutrazol benzoic acid eutectic, is prepared by the following method:
(1) formation of paclobutrazol solution:Paclobutrazol is taken, normal propyl alcohol is added, ultrasonic dissolution obtains paclobutrazol solution;By matter
The amount ratio of gauge, paclobutrazol and normal propyl alcohol is 1: 5;
(2) formation of benzoic acid solution:Benzoic acid is taken, water is added, ultrasonic disperse obtains benzoic acid aqueous solution;By quality
The amount ratio of meter, benzoic acid and water is 1: 10;
(3) formation of paclobutrazol benzoic acid eutectic:Benzoic acid aqueous solution is added dropwise into paclobutrazol solution, stirring is anti-at room temperature
It answers, solid is first precipitated and is redissolved, filters to take filtrate after reacting 2hr, filtrate and ethyl alcohol is mixed to get mixed liquor, mixed liquor is in 45
Solvent is evaporated off in DEG C backspin, obtains paclobutrazol benzoic acid eutectic;By mol, the amount ratio of paclobutrazol and benzoic acid is 1.2: 1;It presses
Stereometer, filtrate and ethyl alcohol mixing ratio are 1: 3.0.
Performance characterization
1, the XRPD collection of illustrative plates of paclobutrazol benzoic acid eutectic (has apparent area with stable crystal form Fig. 2 of paclobutrazol as shown in Figure 1
Not), simulation, which calculates, finds that paclobutrazol benzoic acid eutectic monoclinic system, axial length are And c=
15.2132, shaft angle α=γ=90 ° and β=100 °.
2, nuclear-magnetism test is found, in paclobutrazol benzoic acid eutectic, the molar ratio of paclobutrazol and benzoic acid is 1: 1.
3, solubility test:It is put into 100mg samples in reaction bulb, 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, the 200 μ l... summation of front additive amount (additive amount be), add bottle in rear plug every time
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 benzoic acid eutectic is 13.5mg/
Ml, solubility of the paclobutrazol benzoic acid 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 samples are respectively put into multiple vials, respectively opening be positioned over 0 DEG C/30%RH, 25 DEG C/60%RH
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).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 benzoic acid 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.
2 stability of table is tested
5, stability of solution is tested
0.5,2.0 and 10.0mg samples/ml aqueous solutions are prepared respectively, are respectively placed in closed vial, are put respectively
It is placed in 25 DEG C/60%RH and 40 DEG C/75%RH and observes whether it has solid precipitation, the purity of test sample in lower 10 days and 60 days
(gas chromatography-mass spectrometry combination analysis).Parallel test 5 times, is averaged.Test result is as shown in table 3.The display of table 3,
The aqueous solution of paclobutrazol benzoic acid eutectic placed 10 days and 60 days at 25 DEG C/60%RH and 40 DEG C/75%RH after solubility
It keeps stable with purity, there is preferable stability.
3 stability of solution of table is tested
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 method improving triazole type plant growth regulator paclobutrazol solubility, which is characterized in that paclobutrazol to be prepared into
Paclobutrazol benzoic acid eutectic, the paclobutrazol benzoic acid eutectic are monoclinic system, and axial length is
And c=15.2132, shaft angle α=γ=90 ° and β=100 °.
2. a kind of method improving triazole type plant growth regulator paclobutrazol solubility according to claim 1, special
Sign is, is radiated using Cu-K α, the X-ray powder diffraction figure that the paclobutrazol benzoic acid eutectic is indicated with 2 θ angles have with
Lower characteristic peak:5.3 ± 0.2 °, 5.7 ± 0.2 °, 7.7 ± 0.2 °, 14.2 ± 0.2 ° and 24.0 ± 0.2 °.
3. a kind of method improving triazole type plant growth regulator paclobutrazol solubility according to claim 2, special
Sign is that the paclobutrazol benzoic acid eutectic has following characteristics peak with the X-ray powder diffraction figure that 2 θ angles indicate:4.6±
0.2°,5.3±0.2°,5.7±0.2°,7.7±0.2°,9.5±0.2°,10.0±0.2°,14.2±0.2°,18.0±0.2°
With 24.0 ± 0.2 °.
4. a kind of method improving triazole type plant growth regulator paclobutrazol solubility according to claim 3, special
Sign is that the paclobutrazol benzoic acid eutectic has following characteristics peak with the X-ray powder diffraction figure that 2 θ angles indicate:4.6±
0.2°,5.3±0.2°,5.7±0.2°,6.4±0.2°,7.7±0.2°,9.5±0.2°,10.0±0.2°,14.2±0.2°,
18.0 ± 0.2 °, 24.0 ± 0.2 °, 27.2 ± 0.2 ° and 33.3 ± 0.2 °.
5. a kind of method improving triazole type plant growth regulator paclobutrazol solubility according to claim 4, special
Sign is that the paclobutrazol benzoic acid eutectic has following characteristics peak and its phase with the X-ray powder diffraction figure that 2 θ angles indicate
To intensity:
6. a kind of method improving triazole type plant growth regulator paclobutrazol solubility according to claim 5, special
Sign is, in the paclobutrazol benzoic acid eutectic, the molar ratio of paclobutrazol and benzoic acid is 1: 1.
7. a kind of method improving triazole type plant growth regulator paclobutrazol solubility according to claim 6, special
Sign is that solubility of the paclobutrazol benzoic acid eutectic in 25 DEG C of water is 10~15mg/mL.
8. a kind of method improving triazole type plant growth regulator paclobutrazol solubility according to claim 7, special
Sign is that the paclobutrazol benzoic acid eutectic is prepared by the following method:
(1) formation of paclobutrazol solution:Paclobutrazol is taken, organic solvent is added, ultrasonic dissolution obtains paclobutrazol solution;By quality
The amount ratio of meter, paclobutrazol and organic solvent is 1: 3~5;Organic solvent selects isopropanol or normal propyl alcohol;
(2) formation of benzoic acid solution:Benzoic acid is taken, water is added, ultrasonic disperse obtains benzoic acid aqueous solution;By mass, benzene
The amount ratio of formic acid and water is 1: 8~10;
(3) formation of paclobutrazol benzoic acid eutectic:Benzoic acid aqueous solution is added dropwise into paclobutrazol solution, is stirred to react at room temperature,
Solid is first precipitated to be redissolved, filtrate is filtered to take after reacting 1.5~2hr, filtrate and ethyl alcohol are mixed to get mixed liquor, mixed liquor in
Solvent is evaporated off in 40~45 DEG C of backspins, obtains paclobutrazol benzoic acid eutectic;By mol, the amount ratio of paclobutrazol and benzoic acid is
1.0~1.2: 1;By volume, filtrate and ethyl alcohol mixing ratio are 1: 2.5~3.0.
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Citations (7)
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|---|---|---|---|---|
| GB2041927A (en) * | 1979-02-09 | 1980-09-17 | Ici Ltd | Enantiomers of triazole compounds |
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| CN102238870A (en) * | 2008-09-24 | 2011-11-09 | 先正达有限公司 | Co-crystals |
| CN102595879A (en) * | 2009-11-06 | 2012-07-18 | 巴斯夫欧洲公司 | Crystalline complexes of 4-hydroxy benzoic acid and selected pesticides |
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| CN105828614A (en) * | 2013-12-19 | 2016-08-03 | 日本曹达株式会社 | Co-crystal production method |
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|---|---|---|---|---|
| GB2041927A (en) * | 1979-02-09 | 1980-09-17 | Ici Ltd | Enantiomers of triazole compounds |
| GB2080795A (en) * | 1980-07-28 | 1982-02-10 | Ici Ltd | Separation of optical isomers of 1-(4-chlorophenyl)-4,4-dimethyl-2- (1,2,4-triazol-1-yl)-pentan-3-ol |
| CN102238870A (en) * | 2008-09-24 | 2011-11-09 | 先正达有限公司 | Co-crystals |
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| 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 |
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