CN1685815A - Beta cyclodextrin parachlorophenoxy acetic acid solid inclusion compound and its preparation and application - Google Patents

Beta cyclodextrin parachlorophenoxy acetic acid solid inclusion compound and its preparation and application Download PDF

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Publication number
CN1685815A
CN1685815A CN 200510041930 CN200510041930A CN1685815A CN 1685815 A CN1685815 A CN 1685815A CN 200510041930 CN200510041930 CN 200510041930 CN 200510041930 A CN200510041930 A CN 200510041930A CN 1685815 A CN1685815 A CN 1685815A
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Prior art keywords
chlorophenoxyacetic acid
beta
schardinger dextrin
inclusion compound
solid inclusion
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CN 200510041930
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CN100508751C (en
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张有明
魏太保
姚虹
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Northwest Normal University
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Northwest Normal University
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Abstract

An inclusion compound in the form of solid used as the plant growth regulator is prepared from beta-cyclodextrin (beta-CD) and p-chlorophenyl oxyacetic acid PcPA through reaction in aqueous solution and recrystallizing.

Description

Beta-schardinger dextrin-p-chlorophenoxyacetic acid solid inclusion compound and preparation thereof and application
Technical field
The present invention relates to a kind ofly directly act on the solid inclusion compound of generation, also relate to the application of the preparation method of this inclusion complex and this inclusion complex simultaneously as plant growth regulator by beta-schardinger dextrin-and p-chlorophenoxyacetic acid.
Background technology
Cyclodextrin (being called for short CD) is to pass through 1, the tubbiness molecule that the 4-glycosidic bond is formed by connecting by six to eight ring glucose units.Usually be called for short α-CD (6), β-CD (7), γ-CD (8).β-CD has strong hydrophobicity cavity structure, it is a representational host molecule, as guest molecule size and physicochemical property and β-when the CD cavity is complementary, can rely on Van der Waals force, hydrophobic effect power, effects such as hydrogen bond, the part of various guest molecules of inclusion or molecule forms inclusion complex, because β-CD special construction and unusual envelope function, and it is nontoxic, inexpensive should getting, therefore be widely used in chemistry, fields such as medicine and food industry, and agriculturally show specific function, as producing detoxifcation after β-CD and the action of agricultural chemicals, stable, slow release long-acting and solubilising effect.
P-chlorophenoxyacetic acid (has another name called: P CP A) be the granular crystal of a colorless and odorless, molecular weight is 200.5, absorption multifunctional plant growth regulator in belonging to, the balance that can regulate the plant corpus internal hormone stimulates ovary to expand, and replenishes growth hormone deficiency in the plant corpus, promotes the biosynthesis in the plant corpus.It also is a kind of selective herbicide, it can promote plant germination and growth, promote setting, prevent the crop fruit drop, ripen in advance, improve output, increase the crop protein content, induce the generation of seedless tomatoes and no seed glucose, and can increase the fruit of crop, especially to having the crop of many ovules, more remarkable as tomato, eggplant, fig etc.Select suitable means when also finding to use this product simultaneously, change spraying medicine concentration, time and position etc., can promote or suppress the physiology course of plant, thereby reach people's its intended purposes.This product formulation rate is minimum, and general 0.006-0.01% just can make the various different remarkable results of deposits yields of doing.But p-chlorophenoxyacetic acid dissolubility in water is little, and human body and plant are all had excitant.
Summary of the invention
The objective of the invention is to have irritating shortcoming, directly act on, be prepared into the beta-schardinger dextrin-p-chlorophenoxyacetic acid solid supermolecule inclusion complex that plant growing is had regulatory function with beta-schardinger dextrin-and p-chlorophenoxyacetic acid in order to overcome chlorophenoxyacetic acid.
Another object of the present invention provides the preparation method of beta-schardinger dextrin-p-chlorophenoxyacetic acid solid inclusion compound.
A further object of the invention: just provide of the concrete application of beta-schardinger dextrin-p-chlorophenoxyacetic acid solid inclusion compound as plant growth regulator.
Purpose of the present invention realizes by following measure:
A kind of beta-schardinger dextrin-p-chlorophenoxyacetic acid solid inclusion compound is by host molecule beta-schardinger dextrin-and guest molecule p-chlorophenoxyacetic acid P CP AThe recrystallization product that in 10～20% ethanol waters, reacts.
Described beta-schardinger dextrin-p-chlorophenoxyacetic acid solid inclusion compound is by host molecule beta-schardinger dextrin-and guest molecule p-chlorophenoxyacetic acid P CP A℃ 1～36 hour the recrystallization product of following reaction in room temperature～90.
A kind of preparation method of beta-schardinger dextrin-p-chlorophenoxyacetic acid solid inclusion compound is that p-chlorophenoxyacetic acid is added drop-wise in the aqueous solution of beta-schardinger dextrin-after with dissolve with ethanol, ℃ down separates out the white product recrystallization after 1～36 time of reaction in room temperature～90 and gets.
With the described white product of separating out respectively with distilled water and washing with acetone recrystallization and get.
The mol ratio of described beta-schardinger dextrin-and p-chlorophenoxyacetic acid is 1: 0.5～1: 2.
A kind of preparation method of beta-schardinger dextrin-p-chlorophenoxyacetic acid solid inclusion compound, be to be after 1: 0.5～1: 2 ratio is mixed in molar ratio with beta-schardinger dextrin-and p-chlorophenoxyacetic acid, join in 10～20% ethanol waters, ℃ following a stirring fully reacted it in 1～36 hour in room temperature～90; Cool off then, filter, and get with distilled water and washing with acetone recrystallized product respectively.
The technology that the present invention prepares beta-schardinger dextrin-p-chlorophenoxyacetic acid solid inclusion compound is simple, the productive rate height, as be 70-80%.
Beta-schardinger dextrin-p-chlorophenoxyacetic acid solid inclusion compound of the present invention is determined by elementary analysis, the analysis of X-ray powder diffraction that the result shows that β-CD and p-chlorophenoxyacetic acid form 1: 1 inclusion complex, and it consists of: β-CD/P CP A5H 2O, elementary analysis: H%6.275, C%42.72, the phenyl ring of p-chlorophenoxyacetic acid embeds the hydrophobic cavity of β-CD molecule.
The physical mixture of beta-schardinger dextrin-p-chlorophenoxyacetic acid solid inclusion compound of the present invention, beta-schardinger dextrin-, p-chlorophenoxyacetic acid and beta-schardinger dextrin-pair and p-chlorophenoxyacetic acid is measured the top of back discovery p-chlorophenoxyacetic acid and inferior peak through the X-ray powder diffraction, and to appear at 2 θ respectively be 34.020 ° and 22.940 °, and it is 16.120 ° and 22.90 ° that two strong peaks of beta-schardinger dextrin-appear at 2 θ respectively.Above-mentioned characteristic peak occurs in its physical mixture diffraction pattern, the crystal structure that simple physics is mixed can not be influenced separately is described, it is 14.720 ° and 7.340 ° that but two strong peaks of inclusion complex appear at 2 θ respectively, compare with the diffraction pattern of beta-schardinger dextrin-and p-chlorophenoxyacetic acid very big variation has taken place, show to have formed new material, different crystal structures is arranged with reactant.
Beta-schardinger dextrin-p-chlorophenoxyacetic acid solid inclusion compound of the present invention is as plant growth regulator.
Beta-schardinger dextrin-p-chlorophenoxyacetic acid solid inclusion compound of the present invention is as the plant growth regulator active component, because numerous hydroxyls of its molecule outside, compare with p-chlorophenoxyacetic acid and to have stronger hydrophily, soluble in water, therefore inclusion complex of the present invention is simple than the p-chlorophenoxyacetic acid method when the processing plant growth regulator, and in process, can reduce the introducing of other organic reagent as solvent, more environmental protection.Inclusion complex still has good plant growth regulating performance, when inclusion complex uses with identical metering with p-chlorophenoxyacetic acid, p-chlorophenoxyacetic acid is the part of its molecule in the inclusion complex of the present invention, and all the other are all the oligomer of natural sugar, has further reduced the pollution of chemical substance to soil.
Inclusion complex of the present invention can be determined the situation that influences that the wheat radical bud sprouts by it as the biologically active of plant growth regulator:
With inclusion complex of the present invention and auxin substance (2,4-dichlorophenoxyacetic acid, p-chlorophenoxyacetic acid) and beta-schardinger dextrin-be mixed with the aqueous solution of a series of concentration, selected wheat seed is handled the back and is sprouted at the growth hormone growth from solution of all kinds of variable concentrations, observe the sprouting situation, it is long to measure radical, root length and the bud of respectively handling seed after one week, the record of averaging is determined promotion or the inhibitory action concentration that each material has the radical bud growth and is made comparisons.Biological activity test the results are shown in Table 1 and table 2.
Table 1 biologically active example 1
Conditioning agent Concentration (mg/L) Bud long (cm) Root long (cm)
Main root Inferior main root Main root once more
2,4 dichlorophenoxyacetic acids ????10
????1 ????2.96
????0.1 ????13.95 ????1.52 ????1.36 ????1.13
????0.01 ????17.38 ????10.19 ????8.18 ????7.32
????0.001 ????18.82 ????12.17 ????12.51 ????10.33
????0.0001 ????12.31 ????3.72 ????2.68 ????2.3
Parachlorophen-oxyacetic acid ????10
????1 ????3.1
????0.1 ????14.29 ????2.35 ????1.97 ????1.74
????0.01 ????18.98 ????11.78 ????10.71 ????9.21
????0.001 ????17.67 ????13.11 ????11.25 ????9.86
????0.0001 ????12.66 ????4.09 ????3.51 ????3.04
Inclusion complex ????10
????1 ????5.86
????0.1 ????18.78 ????10.28 ????8.77 ????7.74
????0.01 ????17.8 ????13.54 ????11.7 ????10.19
????0.001 ????17.8 ????13.97 ????12.74 ????10.8
????0.0001 ????18.71 ????13.74 ????12.41 ????11.03
Running water ????16.58 ????11.15 ????8.81 ????6.45
Pure water ????18.1 ????10.2 ????9.09 ????7.97
Table 2: biologically active example 2
Conditioning agent Concentration (mg/L) Bud long (cm) Root long (cm)
Main root Inferior main root Main root once more
Inclusion complex ????10
????1 ????8.40
????0.1 ????17.42 ????7.14 ????5.94 ????5.21
????0.01 ????18.73 ????12.5 ????9.55 ????7.24
????0.001 ????17.62 ????13.28 ????11.55 ????9.46
????0.0001 ????17.82 ????13.39 ????10.82 ????8.8
Beta-schardinger dextrin- ????10 ????2.46
????1 ????16.15 ????10.67 ????9.80 ????8.44
????0.1 ????17.07 ????12.67 ????11.32 ????8.79
????0.01 ????17.10 ????11.93 ????8.82 ????6.47
????0.001 ????17.89 ????12.09 ????10.68 ????9.49
????0.0001 ????18.21 ????12.00 ????9.87 ????8.09
Running water ????17.53 ????12.57 ????11.21 ????8.66
Pure water ????17.89 ????7.63 ????5.78 ????4.75
Biological activity test is the result show:
1, inclusion complex of the present invention has certain influence for the rudiment of wheat seed bud, root, suppresses the sprouting of root and bud during high concentration, and the sprouting to root and bud during low concentration has facilitation.
2, inclusion complex of the present invention is little to the concentration gradient of seed germination influence.
3, the present invention and not the parachlorophen-oxyacetic acid of inclusion compare, cyclodextrin p-chlorophenoxyacetic acid solid inclusion compound does not embody the effect of lower promotion growth when low concentration, and compare with natural cyclodextrin, cyclodextrin p-chlorophenoxyacetic acid solid inclusion compound has embodied the effect of plant growth regulator when 10mg/L, the sprouting of radical bud is had inhibitory action.
In sum, beta-schardinger dextrin-p-chlorophenoxyacetic acid solid inclusion compound of the present invention as the plant growth regulator active component, has and important effect in the growth of plant, growth course.At first changed the solvability of guest species in the aqueous solution, formed water-soluble plant growth regulator preferably, secondly also can work to suppress growth at inclusion complex solution to plant radical bud germination process middle and high concentration, and the be hydrolyzed to plant growing of cyclodextrin molecular in system of during low concentration because inclusion complex outside provides nutriment, further promotes the growth of plant.
Beta-schardinger dextrin-p-chlorophenoxyacetic acid solid inclusion compound of the present invention can be used for the growth regulating of vegetables, cereal crops.
Beta-schardinger dextrin-p-chlorophenoxyacetic acid solid inclusion compound of the present invention can be used for preventing early stage fallen flowers, the shedding of fruit crop.
Beta-schardinger dextrin-p-chlorophenoxyacetic acid solid inclusion compound of the present invention can be used for promoting crop precocity, volume increase.
Embodiment
Example 1: the 0.13g p-chlorophenoxyacetic acid slowly is added drop-wise in 100ml β-CD aqueous solution after with the 10ml dissolve with ethanol (contains β-CD1.6g, the mol ratio of β-CD and p-chlorophenoxyacetic acid is 1: 0.5), room temperature reaction after 1 hour the adularescent material separate out, collect precipitate, use 10ml acetone and 10ml water washing precipitate respectively, water be recrystallized product 0.47g, productive rate 27%.
Example 2: the 0.13g p-chlorophenoxyacetic acid slowly is added drop-wise in 100ml β-CD aqueous solution after with the 10ml dissolve with ethanol (contains β-CD1.6g, the mol ratio of β-CD and p-chlorophenoxyacetic acid is 1: 0.5), room temperature reaction after 1 hour the adularescent material separate out, continue to stir and collect precipitate after totally 20 hours, use 10ml acetone and 10ml water washing precipitate respectively, water be recrystallized product 0.52g, productive rate 30%.
Example 3: the 0.13g p-chlorophenoxyacetic acid slowly is added drop-wise in 100ml β-CD aqueous solution after with the 10ml dissolve with ethanol (contains β-CD1.6g, the mol ratio of β-CD and p-chlorophenoxyacetic acid is 1: 0.5), room temperature reaction after 1 hour the adularescent material separate out, continue to stir and collect precipitate after totally 30 hours, use 10ml acetone and 10ml water washing precipitate respectively, water be recrystallized product 0.55g, productive rate 32%.
Example 4: after 2.3g β-CD and 0.4g p-chlorophenoxyacetic acid mixing (mol ratio of β-CD and p-chlorophenoxyacetic acid is 1: 1), be dissolved in 110ml concentration and be and be heated to 40～50 ℃ of reactions in 20% the ethanol water and stop reaction after 35 hours, whiteness is separated out in cooling, collect precipitate, use 10ml acetone and 10ml water washing precipitate respectively, water be recrystallized product 1.76g, productive rate 65%.
Example 5: after 2.3g β-CD and 0.4g p-chlorophenoxyacetic acid mixing (mol ratio of β-CD and p-chlorophenoxyacetic acid is 1: 1), be dissolved in 110ml concentration and be and be heated to 40～50 ℃ of reactions in 10% the ethanol water and stop reaction after 35 hours, whiteness is separated out in cooling, collect precipitate, use 10ml acetone and 10ml water washing precipitate respectively, water be recrystallized product 1.76g, productive rate 65%.
Example 6: after 2.3g β-CD and 0.4g p-chlorophenoxyacetic acid mixing (mol ratio of β-CD and p-chlorophenoxyacetic acid is 1: 1.5), be dissolved in 100ml concentration and be in 15% the ethanol water, be heated to 80～90 ℃ of reactions and stop reaction after 33 hours, whiteness is separated out in cooling, collect precipitate, use 10ml acetone and 10ml water washing precipitate respectively, water be recrystallized product 2.3g, productive rate 85%.
Example 7: the 0.4g p-chlorophenoxyacetic acid slowly is added drop-wise to after with the 10ml dissolve with ethanol in 90ml β-CD aqueous solution of 80 ℃ and (contains β-CD2.3g, the mol ratio of β-CD and p-chlorophenoxyacetic acid is 1: 1), be heated to 80～90 ℃ of reactions and stop reaction after 36 hours, whiteness is separated out in cooling, collect precipitate, use 10ml acetone and 10ml water washing precipitate respectively, water be recrystallized product 1.7g, productive rate 63%.
Example 8: the 0.6g p-chlorophenoxyacetic acid slowly is added drop-wise to after with the 10ml dissolve with ethanol in 90ml β-CD aqueous solution of 80 ℃ and (contains β-CD2.3g, the mol ratio of β-CD and p-chlorophenoxyacetic acid is 1: 1.5), be heated to 80～90 ℃ of reactions and stop reaction after 36 hours, whiteness is separated out in cooling, collect precipitate, use 10ml acetone and 10ml water washing precipitate respectively, water be recrystallized product 2g, productive rate 74%.
Example 9: the 0.8g p-chlorophenoxyacetic acid slowly is added drop-wise to after with the 10ml dissolve with ethanol in 90ml β-CD aqueous solution of 80 ℃ and (contains β-CD2.3g, the mol ratio of β-CD and p-chlorophenoxyacetic acid is 1: 2), be heated to 80～90 ℃ of reactions and stop reaction after 36 hours, whiteness is separated out in cooling, collect precipitate, use 10ml acetone and 10ml water washing precipitate respectively, water be recrystallized product 1.8g, productive rate 67%.
Example 10: the 0.4g p-chlorophenoxyacetic acid slowly is added drop-wise to after with the 20ml dissolve with ethanol in 100ml β-CD aqueous solution of 80 ℃ and (contains β-CD2.3g, the mol ratio of β-CD and p-chlorophenoxyacetic acid is 1: 1), be heated to 80～90 ℃ of reactions and stop reaction after 20 hours, whiteness is separated out in cooling, collect precipitate, use 10ml acetone and 10ml water washing precipitate respectively, water be recrystallized product 1.4g, productive rate 52%.
Above-mentioned experimental result shows that the productive rate of inclusion reaction mainly is subjected to following three factor affecting
Reaction time: also have product to separate out though react after 1 hour, productive rate is very low, along with the growth in reaction time, the productive rate that generates inclusion complex also improves constantly, when being reflected at more than 36 hours, productive rate improves not obvious, so the reaction time should be controlled at 30～36 hours.
Reaction rate of charge: along with the input amount increasing of chlorophenoxyacetic acid, the productive rate that generates inclusion complex improves, but the input amount of chlorophenoxyacetic acid is big, the production cost height, and being 1: 2 o'clock productive rate, the rate of charge of β-CD and p-chlorophenoxyacetic acid descends to some extent, the factor of mixed economy and two aspects of productive rate, the rate of charge of β-CD and p-chlorophenoxyacetic acid preferably adopted 1: 1.
Reaction temperature: reaction temperature is high more, and the productive rate that generates inclusion complex is high more, and general reaction temperature is advisable about 80 ℃.

Claims (7)

1, a kind of beta-schardinger dextrin-p-chlorophenoxyacetic acid solid inclusion compound is characterized in that: be by host molecule beta-schardinger dextrin-and guest molecule p-chlorophenoxyacetic acid P CP AThe recrystallization product that in 10～20% ethanol waters, reacts.
2, beta-schardinger dextrin-p-chlorophenoxyacetic acid solid inclusion compound according to claim 1 is characterized in that: be by host molecule beta-schardinger dextrin-and guest molecule p-chlorophenoxyacetic acid P CP A℃ 1～36 hour the recrystallization product of following reaction in room temperature～90.
3, a kind of preparation method of beta-schardinger dextrin-p-chlorophenoxyacetic acid solid inclusion compound, it is characterized in that: p-chlorophenoxyacetic acid is added drop-wise in the aqueous solution of beta-schardinger dextrin-after with dissolve with ethanol, ℃ down separates out the white product recrystallization after 1～36 time of reaction in room temperature～90 and get.
4, the preparation method of beta-schardinger dextrin-p-chlorophenoxyacetic acid solid inclusion compound as claimed in claim 3 is characterized in that: with the white product separated out respectively with distilled water and washing with acetone recrystallization and get.
5, as the preparation method of claim 3 or 4 described beta-schardinger dextrin-p-chlorophenoxyacetic acid solid inclusion compounds, it is characterized in that: the mol ratio of described beta-schardinger dextrin-and p-chlorophenoxyacetic acid is 1: 0.5～1: 2.
6, a kind of preparation method of beta-schardinger dextrin-p-chlorophenoxyacetic acid solid inclusion compound, it is characterized in that: with beta-schardinger dextrin-and p-chlorophenoxyacetic acid is after 1: 0.5～1: 2 ratio is mixed in molar ratio, join in 10～20% ethanol waters, ℃ following a stirring fully reacted it in 1～36 hour in room temperature～90; Cool off then, filter, and get with distilled water and washing with acetone recrystallized product respectively.
7, beta-schardinger dextrin-p-chlorophenoxyacetic acid solid inclusion compound is as the application of plant growth regulator.
CNB2005100419302A 2005-04-04 2005-04-04 Beta cyclodextrin parachlorophenoxy acetic acid solid inclusion compound and preparation and application thereof Expired - Fee Related CN100508751C (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101824144A (en) * 2010-05-15 2010-09-08 西北师范大学 Polyethylene glycol aryloxyacetate, preparation thereof and application as plant growth regulator
CN102093567A (en) * 2010-12-17 2011-06-15 西北师范大学 Cyclodextrin-polyethyleneglycol aryloxyacetate inclusion complex, and preparation and application thereof
CN103404512A (en) * 2013-07-12 2013-11-27 浙江工业大学 Multi-effect triazole cyclodextrin inclusion complex and preparation method thereof

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101824144A (en) * 2010-05-15 2010-09-08 西北师范大学 Polyethylene glycol aryloxyacetate, preparation thereof and application as plant growth regulator
CN102093567A (en) * 2010-12-17 2011-06-15 西北师范大学 Cyclodextrin-polyethyleneglycol aryloxyacetate inclusion complex, and preparation and application thereof
CN103404512A (en) * 2013-07-12 2013-11-27 浙江工业大学 Multi-effect triazole cyclodextrin inclusion complex and preparation method thereof
CN103404512B (en) * 2013-07-12 2014-12-17 浙江工业大学 Multi-effect triazole cyclodextrin inclusion complex and preparation method thereof

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