CN107200790B - Chitosan oligosaccharide derivative and preparation method and application thereof - Google Patents
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- 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
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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Abstract
The invention belongs to the technology of ocean chemical engineering, and particularly relates to a chitosan oligosaccharide derivative, and a preparation method and application thereof. The chitosan oligosaccharide derivative is a dithio heterocyclic derivative of chitosan oligosaccharide and is shown in a general formula I, the invention adopts an active substructure splicing principle, takes non-toxic and easily degradable chitosan oligosaccharide as a lead compound, introduces a bioactive group of the dithio heterocyclic derivative into a natural product chitosan oligosaccharide framework, prepares a novel chitosan oligosaccharide derivative with improved thread killing activity and induced resistance, and simultaneously, the synthesized derivative can keep the characteristics of good water solubility, natural non-toxicity, easy degradation and good biocompatibility of the chitosan oligosaccharide. Therefore, the dosage of chemical pesticides is reduced, the residue is reduced, the pollution is reduced, and a new way for developing novel biological pesticides is opened up.
In the formula (I), the compound is shown in the specification,
Description
Technical Field
The invention belongs to the technology of ocean chemical engineering, and particularly relates to a chitosan oligosaccharide derivative, and a preparation method and application thereof.
Background
China is a big agricultural country, and in order to improve the grain yield and deal with the population pressure, China uses a large amount of chemical pesticides for a long time on agricultural production, thereby bringing about increasingly sharp environmental problems and ecological problems. Meanwhile, with the improvement of environmental awareness and food safety awareness of people, people are also paying more attention to the food safety problem caused by pesticide residues. China puts environmental protection and food safety into priority when national policies are set, and in order to ensure food safety of people and protect natural ecology, a sustainable development strategy is set, so that the development of efficient, low-toxicity and low-residue biopesticides is urgent.
China is also a big ocean country at the same time, and the method utilizes abundant marine organism resources to develop marine organism source pesticides, and is a new research field with wide application prospects. Chitin is derived from shells of arthropods (crustacean and insect) such as shrimp, crab and insect, shells of mollusks, and cell walls of fungi and lower algae. It is rich in content, renewable, and the second largest natural biological polysaccharide with the content second to cellulose. Chitosan can be obtained by deacetylating chitin, and chitosan oligosaccharide with polymerization degree of 2-20 can be obtained by special biological enzyme technology, chemical degradation or microwave degradation technology. The chitosan oligosaccharide has the characteristics of no toxicity, good water solubility, good biocompatibility, natural degradation and the like.
The research shows that the chitosan and the chitosan oligosaccharide can regulate the microbial population of the soil, stimulate the microorganisms in the soil to generate nematicidal substances and reduce the amount and the harm degree of nematodes in the corresponding soil. In addition, researches show that the oligosaccharide can promote the formation of plant callus, activate plant cells, promote the growth of plants and improve the biomass. Meanwhile, the chitosan oligosaccharide can promote the activation of various beneficial enzymes such as plant polysaccharase, catalase and the like, and induce plants to generate antitoxin or phytoalexin so as to resist pathogen invasion and improve the immunity. At present, a plurality of products of marine organism pesticides developed by taking chitosan and oligosaccharide as raw materials are on the market. However, chitosan oligosaccharide is a natural product, has no line killing activity, and has a large difference from chemical pesticides in indirect line killing activity, so that the popularization is difficult, and the application of the chitosan oligosaccharide is limited.
Sulfur is an important element constituting life, and many sulfur-containing compounds have various important physiological activities. In plant protection, many highly effective pesticides, herbicides, fungicides, and nematicides are sulfur-containing compounds. The dithiocarbamate compounds are high-efficiency agricultural bactericides and nematicides with wide application. If the compound is a dithiocarbamate nematicide, the compound can be degraded into methyl isothiocyanate in soil to play a fumigating role, and root-knot nematodes can be effectively killed by inhibiting biological cell division, synthesis of biomacromolecules and resistance to biological respiration. However, such a nematicide has skin toxicity, is toxic to growing plants, has few commercial varieties, and is expensive, and thus there is an urgent need for a nematicide that is environmentally friendly.
Disclosure of Invention
Aiming at the problems, the invention provides a chitosan oligosaccharide derivative with novel structure and good thread killing activity, and a preparation method and application thereof.
In order to achieve the above purpose of the present invention, the present invention adopts the following technical scheme:
a chitosan oligosaccharide derivative is a disulfide heterocyclic derivative of chitosan oligosaccharide shown in a general formula I,
in the formula (I), the compound is shown in the specification,
n＝2-20。
a process for preparing the derivative of chitosan oligosaccharide includes dissolving chitosan oligosaccharide in the mixture of alcohol and water, and reaction between chitosan oligosaccharide and dithiol at ordinary temp in the presence of alkaliCarbonizing for 5-6h, and reacting with methyl bromide or 1, 2-dibromoethane for 6-12h to obtain a reaction product shown in formula I
The chitosan oligosaccharide dithiobutane heterocycle derivative or the formula I
The chitosan oligosaccharide dithiolane heterocyclic derivative of (1); wherein, taking chitosan oligosaccharide as a reference, the molar ratio of the chitosan oligosaccharide, alkali, carbon disulfide and methyl bromide or 1, 2-dibromoethane is 1:1.5-2:1.5-2: 1.5-2.
Dissolving the reaction product in water, precipitating with ethanol, washing with alcohol, dissolving in water, and lyophilizing to obtain purified product shown in formula I
The chitosan oligosaccharide dithiobutane heterocycle derivative or the formula I
The chitosan oligosaccharide dithiolane heterocyclic derivative of (1).
The molecular weight of the chitosan oligosaccharide is 320-3200.
The mass ratio of the volume of the mixed solution to the chitosan oligosaccharide is 25: 1-2; wherein the mixed solution is alcohol and water, and the volume ratio of the alcohol to the water is 4: 0.5-1.
The alcohol is methanol or ethanol.
The alcohol in the alcohol washing is methanol or ethanol.
The application of the chitosan oligosaccharide dithio-heterocyclic derivative shown in the general formula I in preparing a nematicide.
The principle is as follows: the amino group of the chitosan oligosaccharide molecule can generate nucleophilic reaction with carbon disulfide to generate amino dithioformate, and then further generate electrophilic substitution in the presence of small molecule monobromide or polybromide to finally generate a 2-substituted disulfide ring.
The invention has the advantages that: the dithiocarbamates pesticide is a large class of agricultural pesticide for killing insects and fungi, disulfide active groups of the dithiocarbamates pesticide have high activity, and disulfide heterocycles are one of the derivatization directions of dithiocarbamates; the invention adopts the active substructure splicing principle, takes nontoxic and degradable chitosan oligosaccharide as a lead compound, introduces the bioactive group of the dithio-heterocyclic derivative into the skeleton of the natural product, namely the chitosan oligosaccharide, and prepares the chitosan oligosaccharide derivative with improved thread killing activity and induced resistance, and meanwhile, the synthesized derivative can keep the characteristics of good water solubility, naturalness, no toxicity, easy degradation and good biocompatibility of the chitosan oligosaccharide. Therefore, the dosage of chemical pesticides is reduced, the residue is reduced, the pollution is reduced, and a new way for developing biological pesticides is opened up.
Drawings
FIG. 1 is an infrared spectrum of chitosan oligosaccharide provided in the example of the present invention, which shows characteristic absorption in the infrared (cm)-1)：1650，1589，1374，1315，1024，893。
FIG. 2 is an infrared spectrum of a chitooligosaccharide derivative 1 according to an embodiment of the present invention, which shows characteristic absorption in the infrared (cm)-1)：1633，1556，1533，1372，1311，1205，938，594，576。
FIG. 3 is an infrared spectrum of chitooligosaccharide derivative 2 according to the example of the present invention, which shows characteristic absorption in the infrared (cm)-1)：1574，1506，1373，1311，1021，895，849，588，571。
Detailed Description
The present invention is further described with reference to the drawings attached to the specification, and the scope of the present invention is not limited to the following examples.
EXAMPLE 1 preparation of derivative 1
Adding 2g of chitosan oligosaccharide with the molecular weight of 1500 into 20ml of ethanol, adding 5ml of deionized water, stirring, slowly dropwise adding 2ml of 45% NaOH solution, and alkalizing for 1h after dropwise adding; slowly dripping 1.035ml of carbon disulfide into the reaction system, and reacting for 5 hours at normal temperature; adding 1.5ml of methyl bromide into the reaction system, and reacting for 6 hours at normal temperature; and after the reaction is finished, performing suction filtration, adding 10ml of deionized water into a filter cake for dissolving, adding 20ml of absolute ethyl alcohol for precipitating yellow solid, collecting the solid, washing the solid for 2 times by using the absolute ethyl alcohol, and performing freeze drying to obtain 2.2g of reddish brown particles, namely the derivative 1: chitosan oligosaccharide-2-imine-1, 3-diAnd (3) sulfur butane. The structure is shown in general formula I (
n＝2-20)
The infrared spectrum shows that: the infrared spectrum of the chitosan oligosaccharide derivative 1 (figure 2) is at 1589cm in comparison with that of the chitosan oligosaccharide (figure 1)-1A characteristic absorption peak of NH of (a) decreases, indicating that NH2 has reacted; and 1533cm-1C-N characteristic absorption peak appears; 1205cm-1An S-C-S characteristic absorption peak appears; in conclusion, the synthesis of derivative 1 was successfully demonstrated.
Example 2 preparation of derivative 2
Adding 2g of chitosan oligosaccharide with the molecular weight of 1500 into 20ml of ethanol, adding 5ml of deionized water, stirring, slowly dropwise adding 2ml of 48% NaOH solution, and alkalizing for 1h after dropwise adding; slowly dripping 2.5ml of 1, 3-dibromoethane into the reaction system, and reacting for 6 hours at normal temperature; and after the reaction is finished, performing suction filtration, adding 10ml of deionized water into a filter cake for dissolving, adding 20ml of absolute ethyl alcohol for precipitating yellow solid, collecting the solid, washing for 2 times by using the absolute ethyl alcohol, and freeze-drying to obtain 2.2g of reddish brown solid, namely the chitosan oligosaccharide-2-imine-1, 3-dithiopentane. Namely, the derivative 2: chitosan oligosaccharide-2-imine-1, 3-dithiopentane. The structure is shown in general formula I (
n＝2-20)
The infrared spectrum shows that: the infrared spectrum of the chitosan oligosaccharide derivative 1 (figure 3) is at 1589cm in comparison with that of the chitosan oligosaccharide (figure 1)-1The characteristic absorption peak of NH of (a) decreases, indicating that the amino group has reacted; and 1506cm-1C-N characteristic absorption peak appears; 895cm-1The peak appears as a characteristic peak of S-C. In conclusion, the successful synthesis of derivative 2 was demonstrated.
Determination of thread-killing Activity
The nematicidal activity of the samples against Meloidogyne incognita (melodogyne incognita) was determined by the insect-soaking method. The test was performed at 3 sample concentrations: 0.25mg/ml, 0.13mg/ml and 0.063mg/ml, and an inhibitory effect on Meloidogyne incognita.
The experiment takes ivermectin medicament with the same concentration as a positive control and takes distilled water as a negative control. The method refers to the agricultural ministry standard NY/T1833.1-2009, and comprises the following specific steps:
selecting root-knot nematode egg mass from living host plant, placing on wet filter paper of culture dish, and incubating at 20-25 deg.C to obtain second-instar larva with consistent instar. A10 mg/ml sample stock solution was prepared and diluted to 0.5mg/ml, 0.25mg/ml and 0.13mg/ml in this order. Sequentially sucking the liquid medicine and 100 mul of contrast from low concentration to high concentration by a pipette, respectively adding into a 24-well plate, sucking 100 mul of prepared nematode suspension, adding into the 24-well plate, uniformly mixing the liquid medicine and the nematode suspension in equal amount, and covering for constant-temperature culture at 25 ℃ for 24 h. And observing the death condition of the nematodes under a dissecting mirror after each treatment is repeated for 4 times, and recording the number of the investigated busworms and the number of dead wireworms. Dead nematodes are stiff and cannot move in a bending manner when touched by a hair pin.
The mortality in percent (%) was calculated for each treatment based on the root cause survey data. And (4) calculating according to the following formula, wherein the calculation result is reserved to the last two decimal points:
in the formula:
p-mortality
K-number of dead nematode
N-number of bus worms investigated
The results are shown in Table 1
Table 1 shows the inhibitory activity of chitosan oligosaccharide derivatives of general formula 1 on Meloidogyne incognita
From the above data and structural analysis it can be seen that: the derivative of the invention has obviously improved thread killing activity compared with chitosan oligosaccharide, and the activity is higher than that of the commercialized thread killing antibiotic ivermectin, especially the derivative 2 has the highest activity which is 20 percent higher than that of the ivermectin. Further, it is considered that, according to the measurement, the substitution degree of the disulfide group is about 20%, and when the derivative concentration is 0.25mg/ml, the equivalent concentration of the disulfide group is about 0.05mg/ml, which is much higher than the thread-killing activity at this concentration. Therefore, the derivative has good thread killing activity. According to the derivative, the disulfide group active group is a small molecule, is only connected to about 20% of monosaccharides, is small in steric hindrance, does not change the main structure of the chitosan oligosaccharide, and therefore does not affect the plant regulation effect of the chitosan oligosaccharide chain. Therefore, the derivative of the invention has the specific thread killing function and the plant regulating function at the same time, thereby playing double roles and improving the effect. The derivative of the invention takes chitosan oligosaccharide as a substrate. The chitosan oligosaccharide is prepared by deacetylating chitin which is a natural polysaccharide, and decomposing acid and alkali or enzyme, and has the advantages of simple preparation process, easily-obtained source, no toxicity and good biocompatibility. After the active group is connected, a large number of glucosamine skeletons cover the toxicity of the disulfide group, and the obtained product has low toxicity. More importantly, chitosan chains are not absorbed by the skin and are therefore less toxic to the skin, which is a place stronger than common dithiocarbamate pesticides. In addition, the chitosan oligosaccharide can be utilized by microorganisms as a carbon source, and the derivative is easy to degrade, can quickly exert a thread killing effect, is not easy to accumulate and has residual toxicity, so that the chitosan oligosaccharide is environment-friendly.
In addition, the current commercial nematocides are either highly toxic or water-soluble. In the case of the antibiotic ivermectin, it is insoluble in water, although it is of low toxicity. If the compound is used, the compound needs to be prepared into dosage forms such as missible oil and the like which need organic reagents, thus causing resource waste and environmental hazard invisibly. The derivative of the invention is dissolved in water, and the solubility is more than 2mg/ml, so the derivative is convenient to use in practice, does not cause additional pollution, is not easy to remain, and is safe and green.
In conclusion, the invention opens up a new way for increasing the variety of the nematocides, reducing the dosage of chemical pesticides, reducing residues and pollution and developing biological pesticides.
Claims (8)
1. A chitosan oligosaccharide derivative for use in the preparation of a nematicide, wherein: the chitosan oligosaccharide derivative is a disulfide heterocyclic derivative of chitosan oligosaccharide and is shown in a general formula I,
in the formula (I), the compound is shown in the specification,
or
，n=2-20。
2. The method for preparing a chitosan oligosaccharide derivative for the preparation of nematocides as claimed in claim 1, wherein: reacting chitosan oligosaccharide with carbon disulfide at normal temperature for 5-6h in a mixed solution of alcohol and water in the presence of alkali, and then reacting with methyl bromide or 1, 2-dibromoethane for 6-12h to obtain a reactant shown as formula I
The chitosan oligosaccharide dithiobutane heterocycle derivative or the formula I
The chitosan oligosaccharide dithiolane heterocyclic derivative of (1); wherein the molar ratio of the chitosan oligosaccharide, the alkali, the carbon disulfide and the methyl bromide or the 1, 2-dibromoethane is 1:1.5-2:1.5-2: 1.5-2.
3. The method for preparing a chitosan oligosaccharide derivative for the preparation of nematicides according to claim 2, wherein: dissolving the reaction product in water, precipitating with ethanol, washing with alcohol, dissolving in water, and lyophilizing to obtain purified product shown in formula I
The chitosan oligosaccharide dithiobutane heterocycle derivative or the formula I
The chitosan oligosaccharide dithiolane heterocyclic derivative of (1).
4. The preparation method of the chitosan oligosaccharide derivative for the preparation of nematicides according to claim 2 or 3, wherein: the molecular weight of the chitosan oligosaccharide is 320-3200.
5. The method for preparing a chitosan oligosaccharide derivative for the preparation of nematicides according to claim 2, wherein: the mass ratio of the volume of the mixed solution to the chitosan oligosaccharide is 25: 1-2; wherein the mixed solution is alcohol and water, and the volume ratio of the alcohol to the water is 4: 0.5-1.
6. The preparation method of the chitosan oligosaccharide derivative for the preparation of nematicides according to claim 2 or 5, wherein: the alcohol is methanol or ethanol.
7. The method for preparing a chitosan oligosaccharide derivative for the preparation of nematocides as claimed in claim 3, wherein: the alcohol in the alcohol washing is methanol or ethanol.
8. Use of a chitosan oligosaccharide derivative for the preparation of nematicides according to claim 1, characterized in that: the application of the chitosan oligosaccharide dithio-heterocyclic derivative shown in the general formula I in preparing a nematicide.
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