CN103385246B - Hydroxypropyl-beta-cyclodextrin inclusion complex of chlorpropham, preparation method and applications thereof - Google Patents
Hydroxypropyl-beta-cyclodextrin inclusion complex of chlorpropham, preparation method and applications thereof Download PDFInfo
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- CWJSHJJYOPWUGX-UHFFFAOYSA-N chlorpropham Chemical compound CC(C)OC(=O)NC1=CC=CC(Cl)=C1 CWJSHJJYOPWUGX-UHFFFAOYSA-N 0.000 title claims abstract description 80
- 239000005647 Chlorpropham Substances 0.000 title claims abstract description 77
- ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 title claims abstract description 58
- 238000002360 preparation method Methods 0.000 title claims description 7
- 235000002595 Solanum tuberosum Nutrition 0.000 claims abstract description 26
- 244000061456 Solanum tuberosum Species 0.000 claims abstract description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 230000005764 inhibitory process Effects 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 9
- 238000004108 freeze drying Methods 0.000 claims description 6
- 239000000706 filtrate Substances 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 2
- 238000000227 grinding Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 abstract description 5
- 239000002552 dosage form Substances 0.000 abstract 1
- 238000010591 solubility diagram Methods 0.000 description 7
- 229920000858 Cyclodextrin Polymers 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 229950005162 benexate Drugs 0.000 description 4
- IAXUQWSLRKIRFR-SAABIXHNSA-N chembl2104696 Chemical compound C1C[C@@H](CNC(=N)N)CC[C@@H]1C(=O)OC1=CC=CC=C1C(=O)OCC1=CC=CC=C1 IAXUQWSLRKIRFR-SAABIXHNSA-N 0.000 description 4
- 230000003381 solubilizing effect Effects 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000003905 agrochemical Substances 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000001149 thermolysis Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000035784 germination Effects 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 238000005374 membrane filtration Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 239000001116 FEMA 4028 Substances 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 1
- 235000011175 beta-cyclodextrine Nutrition 0.000 description 1
- 229960004853 betadex Drugs 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 230000005059 dormancy Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000012417 linear regression Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000302 molecular modelling Methods 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
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- Medicinal Preparation (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Abstract
The invention discloses a hydroxypropyl-beta-cyclodextrin inclusion complex, the inclusion complex is composed of host molecules and guest molecules, the host molecules are hydroxypropyl-beta-cyclodextrin, the guest molecules are chlorpropham, and the inclusion ratio of hydroxypropyl-beta-cyclodextrin to chlorpropham is 1:1. The inclusion complex perfectly solves the problems of bad water solubility and thermal stability of chlorpropham, improves the biological utilization of chlorpropham, avoids a large amount usage of other organic solvents of chlorpropham in other dosage forms, and has a very good application on potato bud inhibition.
Description
Technical field
The invention belongs to pesticide field, be specifically related to the spirit of a kind of parachloroanilinum and there is the inclusion compound of solubilizing effect, preparation method and the application in potato bud inhibition.
Background technology
Potato sprouting after dormancy will cause the reduction of potato dehydration, nutritional quality, therefore seriously constrains the development of Potato Industry.Can the germination of inhibition of potato effectively under the low temperature of 1 ~ 5 DEG C by storage of potato, but low temperature storage can make potato starch saccharification, thus cause product brown stain man-hour and affect its mouthfeel adding.Therefore, potato often uses the germination that Suckering agents carrys out inhibition of potato in storage.Chlorpropham (CIPC) is the most effective and widely used potato bud inhibition agent in the current whole world, but its poorly water-soluble (89 mg/L, 25 DEG C), use is often dissolved in methyl alcohol and is disperseed by the potato ventilation storehouse circulatory system as thermal fog, or be made into pulvis and be sprinkling upon on potato, or make missible oil and directly spray, soak potato, but these formulations all can use a large amount of organic solvents to increase the solvability of chlorpropham to improve its bioavilability, thus exacerbate the pollution to environment; Meanwhile, chlorpropham heat endurance is poor, and when using as thermal fog, high temperature is easy to make its thermolysis be harmful material; In addition, chlorpropham itself is a kind of volatile crystal, is not easy to storage, and long-time exposure is harmful to environment and human body in atmosphere.Cyclodextrin has hydrophobic cavity and hydrophilic outer wall, because of water-soluble, stability and bioavilability that it can strengthen agricultural chemicals, reduces toxicity and the Co ntrolled release etc. to agricultural chemicals, is widely used in agriculture field.The present inventor once solved the problems referred to above (see X. Ge by beta-schardinger dextrin-(β-CD) inclusion chlorpropham, J. He, F.M. Qi, Y. Yang, Z. Huang, R.H. Lu, L.Z. Huang, Inclusion complexation of chloropropham with β-cyclodextrin:preparation, characterization and molecular modeling, Spectrochimica Acta Part A, 81 (2011) 397-403.), but research finds that beta-schardinger dextrin-and chlorpropham can form a kind of controlled micro crystallization compound of indissoluble.
Summary of the invention
One of the object of the invention solves existing chlorpropham formulation to use a large amount of organic solvent, and beta-schardinger dextrin-is to the limited problem of its solubilizing effect, provides a kind of and improves the water miscible hydroxypropyl-beta-cyclodextrin inclusion of chlorpropham.
Two of the object of the invention is to provide a kind of method preparing the hydroxypropyl-beta-cyclodextrin inclusion of above-mentioned chlorpropham.
Three of the object of the invention is to provide the hydroxypropyl-beta-cyclodextrin inclusion application of above-mentioned chlorpropham.
It is as follows that the present invention realizes the technical scheme that above-mentioned purpose adopts:
A kind of hydroxypropyl-beta-cyclodextrin inclusion of chlorpropham, described inclusion compound is made up of host molecule and guest molecule, described host molecule is HP-β-CD, and described guest molecule is chlorpropham, and the Host-guest ratio of described HP-β-CD and chlorpropham is 1:1.
Further, the average substitution degree of described HP-β-CD is 4 ~ 9.
The preparation method of the hydroxypropyl-beta-cyclodextrin inclusion of above-mentioned chlorpropham: the HP-β-CD of chlorpropham and equimolar amounts is mixed, add water grinding after 1 ~ 2 hour, the hot water adding 65 ~ 75 DEG C again makes mixture dissolve, then stir 4 ~ 8 hours at 65 ~ 75 DEG C, cooling, filter, after filtrate freeze drying, namely obtain chlorpropham inclusion compound.
The application of the hydroxypropyl-beta-cyclodextrin inclusion of above-mentioned chlorpropham is the application that it can be used as potato bud inhibition agent.
Further, during storage of potato, be evenly sprinkling upon on potato by inclusion compound, the weight ratio of the hydroxypropyl-beta-cyclodextrin inclusion of potato and chlorpropham is 1000:(0.1 ~ 0.3).
Further, inclusion compound water is mixed with the soak of 3 ~ 20g/L, then potato is placed in soak immersion after 3 ~ 5 minutes, lucifuge dries storage.
Beneficial effect: the preparation method of the hydroxypropyl-beta-cyclodextrin inclusion of chlorpropham of the present invention does not use any organic solvent, avoid a large amount of uses of other formulation organic solvents of chlorpropham, and solve that chlorpropham is water-soluble, the problem of poor heat stability well, improve the bioavilability of chlorpropham, in potato bud inhibition, also have good application.
Accompanying drawing explanation
Fig. 1 is the hydroxypropyl-beta-cyclodextrin inclusion (a) of chlorpropham of the present invention and the infrared spectrum comparison diagram of chlorpropham (b) with HP-β-CD (c).
Fig. 2 is the phase solubility diagram of chlorpropham/HP-β-CD.
The phase solubility diagram of Fig. 3 chlorpropham/beta-schardinger dextrin-.
Fig. 4 is the hydroxypropyl-beta-cyclodextrin inclusion (a) of chlorpropham of the present invention and the thermogravimetric/differential thermal comparison diagram of chlorpropham (b) with HP-β-CD (c).
Embodiment
Below in conjunction with drawings and Examples, the present invention is described in further details.
Embodiment 1
By chlorpropham (8.484g, 0.04mol) with average substitution degree be 6.2 HP-β-CD (65g, 0.04mol) mix, add a small amount of water co-ground 2 hours, then proceed in closed container the hot water adding 70 DEG C said mixture is dissolved, and stir 8 hours at 70 DEG C, be cooled to normal temperature also with the membrane filtration of 0.45 μm, finally filtrate be placed in after carrying out freeze drying in freeze drying box and obtain inclusion compound.
Inclusion compound generates demonstration test: the hydroxypropyl-beta-cyclodextrin inclusion of chlorpropham, the infrared spectrogram of chlorpropham and HP-β-CD gathers with Thermo Nicolet AVATAR 360 type Fourier infrared spectrograph respectively, wave-number range: 4000-400 cm
-1, prepare sample with KBr.After generating inclusion compound as can be seen from Figure 1, in chlorpropham molecule, the C=O stretching vibration peak (Δ) of amide groups is by 1697 cm
-1be blue shifted to 1722 cm
-1, and 1597 cm
-1with 1545 cm
-1on place's phenyl ring, C=C stretching vibration peak (●) is blue shifted to 1635 cm respectively
-1with 1598 cm
-1, and intensity also reduces because of the generation of inclusion compound, 901,773 and 683 cm in addition
-1between C-H flexural vibrations peak (■) on the substituted benzene of position disappear.In addition, 3500-3000 cm in inclusion compound
-1-OH the peak at place and 1028 cm
-1the C-O-C peak at place obviously comes to a point.These phenomenons all confirm the generation of inclusion compound.The phenyl ring part that these phenomenons all demonstrate chlorpropham molecule enters the cavity of HP-β-CD and generates inclusion compound.
Phase solubility is tested: phase solubility diagram is that research cyclodextrin is to the common method of medicine or agricultural chemicals solubilizing effect.Joined in 10 mL colorimetric cylinders of same volume variable concentrations HP-β-CD solution by excessive chlorpropham (10 mg), the concentration of HP-β-CD is respectively 0, and 2,4,6,8,10,11,12 mmol/L.Fully vibrate under 25 DEG C of conditions, get the supernatant hydrophylic filter membranes of 0.45 μm and filter after reaching balance, the filtrate obtained use ultraviolet specrophotometer (Varian, Cary-100) after suitable dilution measures at 237 nm places.Equation of linear regression is A=12.465 C (mmol/L)+0.0167, R=0.9993, and HP-β-CD is noiseless in the mensuration of this wavelength place parachloroanilinum spirit.Then with the concentration of HP-β-CD for abscissa, the concentration of chlorpropham is that ordinate draws phase solubility diagram.Conditional formation constant
kccalculated by the straight line of phase solubility diagram, wherein S
0for the intrinsic concentration of chlorpropham when not adding HP-β-CD in water:
（1）
Fig. 2 is the phase solubility diagram of the chlorpropham under variable concentrations HP-β-CD exists, and as can be seen from the figure the solvability of chlorpropham linearly increases along with the increase of HP-β-CD concentration.According to the theory of Higuchi and Connors, this phase solubility diagram can be attributed to A
ltype, namely generate host-guest inclusion than for 1:1 inclusion compound (with Host-guest ratio represent guest molecule be trapped in form inclusion compound in host molecule cavity time, the molecular proportion of Subjective and Objective).Can calculate conditional formation constant according to formula (1) is 728 L/mol.When in solution, the concentration of HP-β-CD reaches 12 mmol/L, the water-soluble of chlorpropham adds about 7.7 times; And the phase solubility (Fig. 3) of parent P-cyclodextrin parachloroanilinum spirit inclusion compound was once studied by research group, find that the increase of beta-schardinger dextrin-parachloroanilinum spirit solvability is more limited, when beta-schardinger dextrin-concentration reaches 2.5 mmol/L, namely a kind of insoluble controlled micro crystallization compound is generated, now CIPC solvability increase only about 2 times, and find that this phase solubility is Ap-Bs type, host-guest inclusion is than being 2:1.This is because HP-β-CD has larger water-soluble and hydrophobic cavity than parent P-cyclodextrin, the HP-β-CD cavity of a part can hold the chlorpropham of a part, and conditional formation constant is greater than the conditional formation constant (225 L/mol) of the Benexate Hydrochloride of chlorpropham, illustrates that the hydroxypropyl-beta-cyclodextrin inclusion of chlorpropham is more stable than the Benexate Hydrochloride of chlorpropham.
Solvability strengthen test: the supersaturated solution preparing chlorpropham, the Benexate Hydrochloride of chlorpropham and the hydroxypropyl-beta-cyclodextrin inclusion of chlorpropham respectively, after abundant stirring, get supernatant filter membrane (0.45 μm) to filter, carry out the mensuration of absorbance in 237 nm places after dilution suitable multiple, according to standard working curve, the results are shown in Table 1 to record solvability.Can find out that, after chlorpropham and HP-β-CD form inclusion compound, the solvability of chlorpropham in water improves more than 4 times, better than the solubilizing effect of beta-schardinger dextrin-parachloroanilinum spirit.
。
Heat endurance strengthen test: Fig. 4 is respectively the hydroxypropyl-beta-cyclodextrin inclusion (a) of chlorpropham and the thermogravimetric/differential thermal comparison diagram of chlorpropham (b) with HP-β-CD (c).HP-β-CD occurs weightless in these 2 stages of 50 ~ 100 DEG C and 330 ~ 380 DEG C, its differential thermal curve corresponding, the former weightlessness for occurring because of dehydration, and the latter is the decomposition because of HP-β-CD and the weightlessness that occurs; Chlorpropham only has a zero-g period (150 ~ 220 DEG C), and the thermolysis that can be attributed to it is weightless; In the hydroxypropyl-beta-cyclodextrin inclusion of chlorpropham, the zero-g period is 240 ~ 280 DEG C, this illustrates that the formation of inclusion compound has delayed the loss in weight of chlorpropham in heating process, and its fusing point peak (50 DEG C) and thermolysis peak (222 DEG C) all disappear in differential thermal curve, these all prove that HP-β-CD and chlorpropham generate Host-guest inclusion complex, and enhance the heat endurance of chlorpropham.
Bud inhibition effect test: table 2 be chlorpropham concentration identical under different inclusion compounds on the impact of potato bud inhibition rate, no matter directly use or immersion treatment, the hydroxypropyl-beta-cyclodextrin inclusion of chlorpropham is all better than the Benexate Hydrochloride of chlorpropham to the bud inhibition effect of potato.
。
Embodiment 2
By chlorpropham (2.137g, 0.01mol) with average substitution degree be 8.64 HP-β-CD (18g, 0.01mol) mix, add a small amount of water co-ground 1 hour, then proceed in closed container the hot water adding 75 DEG C said mixture is dissolved, and stir 4 hours at 75 DEG C, be cooled to normal temperature also with the membrane filtration of 0.45 μm, finally filtrate be placed in after carrying out freeze drying in freeze drying box and obtain inclusion compound.
Claims (6)
1. the hydroxypropyl-beta-cyclodextrin inclusion of a chlorpropham, described inclusion compound is made up of host molecule and guest molecule, it is characterized in that: described host molecule is HP-β-CD, described guest molecule is chlorpropham, and the Host-guest ratio of described HP-β-CD and chlorpropham is 1:1.
2. the hydroxypropyl-beta-cyclodextrin inclusion of chlorpropham according to claim 1, is characterized in that: the average substitution degree of described HP-β-CD is 4 ~ 9.
3. the preparation method of the hydroxypropyl-beta-cyclodextrin inclusion of chlorpropham described in claim 1, it is characterized in that: the HP-β-CD of chlorpropham and equimolar amounts is mixed, add water grinding after 1 ~ 2 hour, the hot water adding 65 ~ 75 DEG C again makes mixture dissolve, then stir 4 ~ 8 hours at 65 ~ 75 DEG C, cooling, filters, namely obtains chlorpropham inclusion compound after filtrate freeze drying.
4. the application of the hydroxypropyl-beta-cyclodextrin inclusion of chlorpropham described in claim 1, is characterized in that: the hydroxypropyl-beta-cyclodextrin inclusion of described chlorpropham is as the application of potato bud inhibition agent.
5. the application of the hydroxypropyl-beta-cyclodextrin inclusion of chlorpropham according to claim 4, it is characterized in that: during storage of potato, be evenly sprinkling upon on potato by inclusion compound, the weight ratio of potato and inclusion compound is 1000:(0.1 ~ 0.3).
6. the application of the hydroxypropyl-beta-cyclodextrin inclusion of chlorpropham according to claim 4, is characterized in that: soak inclusion compound water being mixed with 3 ~ 20g/L, then potato is placed in soak and soaks after 3 ~ 5 minutes, and lucifuge dries storage.
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| CN104642355A (en) * | 2015-02-12 | 2015-05-27 | 鲍祖胜 | Chlorpropham pesticide serving as tobacco bud inhibitor |
| CN107926207A (en) * | 2018-01-10 | 2018-04-20 | 和县绿源蔬菜种植有限责任公司 | Germination accelerating method in a kind of seed potato room |
| US20210022335A1 (en) * | 2018-05-09 | 2021-01-28 | Adama Makhteshim Ltd. | Use of cyclodextrins as agrochemical delivery system |
| WO2019232201A1 (en) * | 2018-06-01 | 2019-12-05 | Bayer Cropscience Lp | Stabilized fungicidal composition comprising cyclodextrin |
| CN110214777A (en) * | 2019-06-05 | 2019-09-10 | 甘肃省农业科学院农产品贮藏加工研究所 | A kind of potato tubers germination regulation sustained release agent prescription and preparation method thereof |
| CN110226600B (en) * | 2019-06-05 | 2021-05-11 | 甘肃省农业科学院农产品贮藏加工研究所 | Dextro-carvone potato sprout inhibitor taking hydroxypropyl-beta-cyclodextrin as slow-release carrier |
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| CN101371660B (en) * | 2008-06-27 | 2011-06-15 | 甘肃省农业科学院农产品贮藏加工研究所 | Sprouting inhibition agent emulsifiable solution for white potato |
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