CN105724429A - Preparing method for degradable modified chitosan bactericide and prepared degradable modified chitosan bactericide - Google Patents
Preparing method for degradable modified chitosan bactericide and prepared degradable modified chitosan bactericide Download PDFInfo
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- CN105724429A CN105724429A CN201610237715.8A CN201610237715A CN105724429A CN 105724429 A CN105724429 A CN 105724429A CN 201610237715 A CN201610237715 A CN 201610237715A CN 105724429 A CN105724429 A CN 105724429A
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- 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
- A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
- A01N59/06—Aluminium; Calcium; Magnesium; Compounds thereof
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- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
Abstract
The invention relates to a preparing method for a degradable modified chitosan bactericide and a prepared degradable modified chitosan bactericide.The preparing method includes the steps that 1, glucosamine, methane sulfonic acid, fumaric acid, benzoyl chloride and thionyl chloride are mixed in an ice-water bath, and then concentrated sulfuric acid is added dropwise to obtain a first mixed solution; 2, chitosan and the reaction mixed solution in the step 1 are mixed for reaction and stirred and stand to obtain a second mixed solution; 3, acetone is added into the second mixed solution in the step 2 until no precipitate is separated, separated precipitate is dissolved into water, and then ammonia water is added dropwise to obtain solid precipitate; 4, the solid precipitate obtained in the step 3, isopropanol and sodium alginate are mixed for reaction to obtain a third mixed solution; 5, the third mixed solution obtained in the step 4 is added dropwise into a calcium chloride water solution and cured to obtain the degradable modified chitosan bactericide.The prepared bactericide is easy to decompose and small in influence on environment.
Description
Technical field
The present invention relates to pesticide field, be specifically related to the preparation method of a kind of degradable modification of chitosan antibacterial and prepared degradable modification of chitosan antibacterial.
Background technology
Antibacterial is also known as biocide, Biocidal algae-killing agent, microbicide etc., it is common that refer to the chemicals of microbial bacterial, fungus and the algae that can efficiently control or kill in water system.In the world, it is common that as the general name of the medicament preventing and treating all kinds of pathogenic microorganisms.
According to investigations, the pathogenic microorganism (fungus, strong bacterium, rickettsia, mycoplasma, virus, algae etc.) of plant pest is had more than 80,000 kinds by the whole world.Agricultural is brought about great losses by plant disease, and global crops thus reduce yield every year on average and are about 500Mt.Once repeatedly occurred in history to cause serious famine because of certain plant disease epidemics, the calamity that even a large amount of populations are hungry to death.Use antibacterial is the cost-effective method of one of controlling plant diseases.
Chinese patent CN103348999B discloses a kind of composite bactericide containing Prochloraz, its component and weight content: the component B of component A and 90%～10% of 10%～90%；Component A is Prochloraz, and component B is Flutriafol.This composite bactericide can be made into emulsion-type antibacterial, powder/grain type antibacterial.This composite bactericide can be used for preventing and treating the disease of vegetable or fruit tree, for instance preventing and treating cucumber anthracnose, anthracnose of tomato, pepper anthracnose, fruit tree dry rot, bamboo rust, Strawberry anthracnose, bitter rot or anthracnose of grape, Semen Caryae Cathayensis dry rot etc..
Chinese patent CN1080995A relates to a kind of agricultural bactericidal composition, appropriate including S-Ethyl ethylthio sulfonate 2-95%, heterocyclic nitrogen-group fungicide 1-65%, auxiliary agent or auxiliary agent and filler, heterocyclic nitrogen-group fungicide therein is any in triazolone, propiconazole, Isoprothiolane or triforine.The agricultural bactericidal composition that this invention proposes, can be widely used in grain, industrial crops, woods fruit flowers, vegetable, foliage-spray, the seed treatment such as melon, waters pouring root dispenser, can effectively prevent and treat because of fungus, antibacterial, the various diseases that virus etc. causes.
But existing antibacterial exists and is difficult to decompose, soil and water source are caused the problems such as long period ground contamination, it would be highly desirable to the antibacterial of exploitation easily degraded.
Summary of the invention
In order to solve the problems referred to above that prior art exists, the invention provides the preparation method of a kind of degradable modification of chitosan antibacterial and prepared degradable modification of chitosan antibacterial, antibacterial prepared by the inventive method easily decomposes, and environmental effect is little.
The technical solution adopted in the present invention is:
The preparation method that the present invention provides a kind of degradable modification of chitosan antibacterial, it is characterized in that, the method includes: a, according to unit mol ratio 1:(0.5-5): (0.5-5): (0.5-5) is added dropwise to concentrated sulphuric acid after glucosamine, Loprazolam, fumaric acid, Benzenecarbonyl chloride. and thionyl chloride being mixed in ice-water bath, obtain the first mixed liquor；Wherein, the volume ratio of concentrated sulphuric acid and Loprazolam is 1:(2-10), the concentration of concentrated sulphuric acid is 90-98 mass %；B, according to mass ratio 1:(15-150) by mixed for gained reaction mixture in chitosan and step a be incorporated in-10 to 10 DEG C of reaction stirrings 1-12 hour after, stand 10-36 hour at-30 to-10 DEG C, obtain the second mixed liquor；C, acetone is joined in step b in gained the second mixed liquor, until no longer there being Precipitation, the precipitation of precipitation being dissolved in the ammonia of dropping 0.5-2 mol/L after water, until no longer there being Precipitation, obtaining solid sediment；D, by gained solid sediment in step c with isopropanol, sodium alginate with mass ratio 1:(10-50): (0.3-3) reacts 12-48 hour after mixing at 25-60 DEG C, obtains the 3rd mixed liquor；E, gained in step d the 3rd mixed liquor is added drop-wise in the calcium chloride water of 0.5-3 mass %, and solidifies 1-10 hour at 15-50 DEG C, obtain degradable modification of chitosan antibacterial.
Preferably, the mixing unit mol ratio of described glucosamine, Loprazolam, fumaric acid, Benzenecarbonyl chloride. and thionyl chloride is 1:(0.7-3): (0.7-3): (0.7-3).
Preferably, the volume ratio of concentrated sulphuric acid described in step a and Loprazolam is 1:(3-7), the concentration of concentrated sulphuric acid is 95-98 mass %.
Preferably, the mixing quality of chitosan described in step b and reaction mixture is than for 1:(30-120).
Preferably, the condition reacting stirring in step b is: temperature is-4 to 5 DEG C, and the time is 6-8 hour, and the condition of standing is: temperature is-20 to-15 DEG C, and the time is 12-20 hour.
Preferably, the concentration of ammonia described in step c is 0.8-1 mol/L.
Preferably, solid sediment described in step d and isopropanol, sodium alginate mixing quality than 1:(20-35): (0.5-2).
Preferably, described in step d, the condition of reaction is: temperature is 30-50 DEG C, and the time is 20-36 hour.
Preferably, the concentration of calcium chloride water described in step e is 1-2 mass %, and the time of solidification is 2-6 hour, and temperature is 30-40 DEG C.
The present invention provides the degradable modification of chitosan antibacterial prepared by preparation method of the present invention.
The invention have the benefit that
One, the antibacterial of the present invention can penetrate in organism, and forms, with the aminoacid within thalline, the purpose that complex compound sediment realizes sterilizing；
Its two, the degradable modification of chitosan antibacterial degradation time of preparation is short, environment will not be caused long lasting effect；
Its three, the present invention uses the raw materials such as chitosan, sodium alginate, calcium chloride to prepare antibacterial, and not only raw material is readily available, and environmental friendliness；
Its four, preparation method of the present invention is simple, it is easy to carry out, it is easy to industrialization and large-scale production.
Detailed description of the invention
For making the object, technical solutions and advantages of the present invention clearly, technical scheme will be described in detail below.Obviously, described embodiment is only a part of embodiment of the present invention, rather than whole embodiments.Based on the embodiment in the present invention, other embodiments all that those of ordinary skill in the art are obtained under the premise not making creative work, broadly fall into the scope that the present invention protects.
The preparation method that the present invention provides a kind of degradable modification of chitosan antibacterial, it is characterized in that, the method includes: a, according to unit mol ratio 1:(0.5-5): (0.5-5): (0.5-5) is added dropwise to concentrated sulphuric acid after glucosamine, Loprazolam, fumaric acid, Benzenecarbonyl chloride. and thionyl chloride being mixed in ice-water bath, obtain the first mixed liquor；Wherein, the volume ratio of concentrated sulphuric acid and Loprazolam is 1:(2-10), the concentration of concentrated sulphuric acid is 90-98 mass %；B, according to mass ratio 1:(15-150) by mixed for gained reaction mixture in chitosan and step a be incorporated in-10 to 10 DEG C of reaction stirrings 1-12 hour after, stand 10-36 hour at-30 to-10 DEG C, obtain the second mixed liquor；C, acetone is joined in step b in gained the second mixed liquor, until no longer there being Precipitation, the precipitation of precipitation being dissolved in the ammonia of dropping 0.5-2 mol/L after water, until no longer there being Precipitation, obtaining solid sediment；D, by gained solid sediment in step c with isopropanol, sodium alginate with mass ratio 1:(10-50): (0.3-3) reacts 12-48 hour after mixing at 25-60 DEG C, obtains the 3rd mixed liquor；E, gained in step d the 3rd mixed liquor is added drop-wise in the calcium chloride water of 0.5-3 mass %, and solidifies 1-10 hour at 15-50 DEG C, obtain degradable modification of chitosan antibacterial.
According to the present invention, the compound that a hydroxyl of glucose is replaced by an amino, molecular formula C6H13O5N; it is commonly called as amino sugar; it is called for short D-glucosamine; have another name called glucamine; be widely present in nature, 2-amino-2-deoxy-D-Glucose generally with N-acetyl derivative (such as chitin) or with N-sulfuric ester and N-acetyl-3-O-lactic acid ether (3-O-.alpha.-carboxyethyl-D-glucosamine .) form be present in microorganism, animal origin polysaccharide and in conjunction with in polysaccharide.Loprazolam is the raw material of medicine and pesticide, also acts as dehydrant, paint solidification accelerator, fibre finish, solvent, alkanisation, esterification and polymerisation catalysts.Catalyst as solvent, esterification and polyreaction.The mixing unit mol ratio of described glucosamine, Loprazolam, fumaric acid, Benzenecarbonyl chloride. and thionyl chloride is preferably 1:(0.7-3): (0.7-3): (0.7-3).
Volume ratio according to the present invention, concentrated sulphuric acid described in step a and Loprazolam is 1:(3-7), the concentration of concentrated sulphuric acid can be 95-98 mass %.
According to the present invention, chitosan (chitosan) is also known as chitosan, being that the chitin (chitin) being widely present by nature obtains through deacetylation, chemical name is Chitosan (1-4)-2-amino-B-D glucose.From 1859, after first Frenchman Rouget obtains chitosan, the premium properties such as the biological functionality of this natural polymer and the compatibility, blood compatibility, safety, microbic resolvability are by all trades and professions extensive concern, and the applied research at numerous areas such as medicine, food, chemical industry, cosmetics, water process, METAL EXTRACTION and recovery, biochemistry and biomedical engineerings achieves major progress.The mixing quality ratio of chitosan described in step b and reaction mixture can be 1:(30-120).
According to the present invention, the condition reacting stirring in step b can be: temperature is-4 to 5 DEG C, and the time is 6-8 hour, and the condition of standing is: temperature is-20 to-15 DEG C, and the time is 12-20 hour.
According to the present invention, the concentration of ammonia described in step c can be 0.8-1 mol/L.
According to the present invention, the mixing quality ratio of solid sediment described in step d and isopropanol, sodium alginate can be 1:(20-35): (0.5-2).
According to the present invention, described in step d, the condition of reaction can be: temperature is 30-50 DEG C, and the time is 20-36 hour.
According to the present invention, the concentration of calcium chloride water described in step e can be 1-2 mass %, and the time of solidification can be 2-6 hour, and temperature can be 30-40 DEG C.
The present invention provides the degradable modification of chitosan antibacterial prepared by preparation method of the present invention.
Further illustrate the present invention following by embodiment, but the present invention is not therefore subject to any restriction.
If no special instructions, instrument of the present invention and reagent are and are purchased, and the commodity of different brands do not affect specifically used.
Embodiment 1
A, according to unit mol ratio 1:0.5:0.5:0.5, glucosamine, Loprazolam, fumaric acid, Benzenecarbonyl chloride. and thionyl chloride are mixed in ice-water bath after be added dropwise to concentrated sulphuric acid, obtain the first mixed liquor；Wherein, the volume ratio of concentrated sulphuric acid and Loprazolam is 1:4, and the concentration of concentrated sulphuric acid is 98 mass %；B, according to mass ratio 1:150 by mixed for gained reaction mixture in chitosan and step a be incorporated in 10 DEG C of reaction stirrings 10 hours after, stand 36 hours at-30 DEG C, obtain the second mixed liquor；C, acetone is joined in step b in gained the second mixed liquor, until no longer there being Precipitation, after the precipitation of precipitation is dissolved in water, dripping the ammonia of 2 mol/L, until no longer there being Precipitation, obtaining solid sediment；D, gained solid sediment in step c is mixed with mass ratio 1:50:3 with isopropanol, sodium alginate after react at 40 DEG C 48 hours, obtain the 3rd mixed liquor；E, gained in step d the 3rd mixed liquor is added drop-wise in the calcium chloride water of 2 mass %, and solidifies 10 hours at 30 DEG C, obtain degradable modification of chitosan antibacterial 1.
Embodiment 2
A, according to unit mol ratio 1:5:5:5, glucosamine, Loprazolam, fumaric acid, Benzenecarbonyl chloride. and thionyl chloride are mixed in ice-water bath after be added dropwise to concentrated sulphuric acid, obtain the first mixed liquor；Wherein, the volume ratio of concentrated sulphuric acid and Loprazolam is 1:6, and the concentration of concentrated sulphuric acid is 90 mass %；B, according to mass ratio 1:100 by mixed for gained reaction mixture in chitosan and step a be incorporated in-10 DEG C of reaction stirrings 1 hour after, stand 20 hours at-10 DEG C, obtain the second mixed liquor；C, acetone is joined in step b in gained the second mixed liquor, until no longer there being Precipitation, after the precipitation of precipitation is dissolved in water, dripping the ammonia of 0.5 mol/L, until no longer there being Precipitation, obtaining solid sediment；D, gained solid sediment in step c is mixed with mass ratio 1:30:1 with isopropanol, sodium alginate after react at 30 DEG C 30 hours, obtain the 3rd mixed liquor；E, gained in step d the 3rd mixed liquor is added drop-wise in the calcium chloride water of 1 mass %, and solidifies 6 hours at 40 DEG C, obtain degradable modification of chitosan antibacterial 2.
Embodiment 3
A, according to unit mol ratio 1:3:3:3, glucosamine, Loprazolam, fumaric acid, Benzenecarbonyl chloride. and thionyl chloride are mixed in ice-water bath after be added dropwise to concentrated sulphuric acid, obtain the first mixed liquor；Wherein, the volume ratio of concentrated sulphuric acid and Loprazolam is 1:8, and the concentration of concentrated sulphuric acid is 95 mass %；B, according to mass ratio 1:15 by mixed for gained reaction mixture in chitosan and step a be incorporated in 0 DEG C of reaction stirring 4 hours after, stand 10 hours at-20 DEG C, obtain the second mixed liquor；C, acetone is joined in step b in gained the second mixed liquor, until no longer there being Precipitation, after the precipitation of precipitation is dissolved in water, dripping the ammonia of 1.5 mol/L, until no longer there being Precipitation, obtaining solid sediment；D, gained solid sediment in step c is mixed with mass ratio 1:10:0.3 with isopropanol, sodium alginate after react at 50 DEG C 12 hours, obtain the 3rd mixed liquor；E, gained in step d the 3rd mixed liquor is added drop-wise in the calcium chloride water of 3 mass %, and solidifies 3 hours at 20 DEG C, obtain degradable modification of chitosan antibacterial 3.
Application Example 1-3
Undertaken the Chinese cabbage leaf suffering from bacterial leaf spot (Herba Cichorii Pseudomonas alba) pulverizing or being applied to the Chinese cabbage seedling planted in booth (is gathered in after 60 days), then it is sprayed onto on the part Chinese cabbage seedling in farmland after the antibacterial dilution prepared by embodiment 1-3, and measure Fungicide residue amount at set intervals, sickness rate adopts counting method to add up, namely a Chinese cabbage has 10% area more than spottiness, namely predicates morbidity.
Calculate with chitosan, adopt method in " ATR/FTIR technology and IR transmission method are for the comparative study of pesticide residues in vegetables medicine assay, " infrared technique ", Xu Lin 2008,30 (12): 702-705 " to measure persticide residue.
Comparison study example
Comparison study example is essentially identical with Application Example processing mode, but is added without antibacterial.
Claims (10)
1. the preparation method of a degradable modification of chitosan antibacterial, it is characterised in that the method includes:
A, according to unit mol ratio 1:(0.5-5): (0.5-5): (0.5-5) is added dropwise to concentrated sulphuric acid after glucosamine, Loprazolam, fumaric acid, Benzenecarbonyl chloride. and thionyl chloride being mixed in ice-water bath, obtain the first mixed liquor；Wherein, the volume ratio of concentrated sulphuric acid and Loprazolam is 1:(2-10), the concentration of concentrated sulphuric acid is 90-98 mass %；
B, according to mass ratio 1:(15-150) by mixed for gained reaction mixture in chitosan and step a be incorporated in-10 to 10 DEG C of reaction stirrings 1-12 hour after, stand 10-36 hour at-30 to-10 DEG C, obtain the second mixed liquor；
C, acetone is joined in step b in gained the second mixed liquor, until no longer there being Precipitation, the precipitation of precipitation being dissolved in the ammonia of dropping 0.5-2 mol/L after water, until no longer there being Precipitation, obtaining solid sediment；
D, by gained solid sediment in step c with isopropanol, sodium alginate with mass ratio 1:(10-50): (0.3-3) reacts 12-48 hour after mixing at 25-60 DEG C, obtains the 3rd mixed liquor；
E, gained in step d the 3rd mixed liquor is added drop-wise in the calcium chloride water of 0.5-3 mass %, and solidifies 1-10 hour at 15-50 DEG C, obtain degradable modification of chitosan antibacterial.
2. preparation method according to claim 1, it is characterized in that, the mixing unit mol ratio of described glucosamine, Loprazolam, fumaric acid, Benzenecarbonyl chloride. and thionyl chloride is 1:(0.7-3): (0.7-3): (0.7-3).
3. preparation method according to claim 1, it is characterised in that the volume ratio of concentrated sulphuric acid described in step a and Loprazolam is 1:(3-7), the concentration of concentrated sulphuric acid is 95-98 mass %.
4. preparation method according to claim 1, it is characterised in that the mixing quality of chitosan described in step b and reaction mixture is than for 1:(30-120).
5. preparation method according to claim 1, it is characterised in that the condition reacting stirring in step b is: temperature is-4 to 5 DEG C, and the time is 6-8 hour, and the condition of standing is: temperature is-20 to-15 DEG C, and the time is 12-20 hour.
6. preparation method according to claim 1, it is characterised in that the concentration of ammonia described in step c is 0.8-1 mol/L.
7. preparation method according to claim 1, it is characterised in that solid sediment described in step d and isopropanol, sodium alginate mixing quality than for 1:(20-35): (0.5-2).
8. preparation method according to claim 1, it is characterised in that described in step d, the condition of reaction is: temperature is 30-50 DEG C, and the time is 20-36 hour.
9. preparation method according to claim 1, it is characterised in that the concentration of calcium chloride water described in step e is 1-2 mass %, the time of solidification is 2-6 hour, and temperature is 30-40 DEG C.
10. the degradable modification of chitosan antibacterial prepared by preparation method described in any one in claim 1-9.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108850024A (en) * | 2018-07-26 | 2018-11-23 | 合肥华盖生物科技有限公司 | A kind of composite highly effective type fungicide and preparation method thereof |
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Application publication date: 20160706 |