WO2017075777A1 - Procédé pour préparer une préparation de pesticide nanométrique à l'aide d'aérogel de silice - Google Patents

Procédé pour préparer une préparation de pesticide nanométrique à l'aide d'aérogel de silice Download PDF

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Publication number
WO2017075777A1
WO2017075777A1 PCT/CN2015/093833 CN2015093833W WO2017075777A1 WO 2017075777 A1 WO2017075777 A1 WO 2017075777A1 CN 2015093833 W CN2015093833 W CN 2015093833W WO 2017075777 A1 WO2017075777 A1 WO 2017075777A1
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Prior art keywords
drug
silica aerogel
pesticide
nano
solvent
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PCT/CN2015/093833
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English (en)
Chinese (zh)
Inventor
张旭旭
张志安
伍超
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清华大学深圳研究生院
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Priority to PCT/CN2015/093833 priority Critical patent/WO2017075777A1/fr
Publication of WO2017075777A1 publication Critical patent/WO2017075777A1/fr

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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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/12—Powders or granules
    • A01N25/14—Powders or granules wettable
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Definitions

  • the invention belongs to the technical field of pesticides, and specifically relates to the application of silica aerogel as a novel carrier in pesticide processing aids.
  • Pesticides are collectively referred to as a class of drugs used in agricultural production to protect and promote the growth of plants and crops, and to kill insecticides, sterilize, and kill harmful animals (or weeds). Specifically, it is used in agriculture to control pests and diseases, and to regulate plant growth, weeding and other agents. Pesticides play an important role in ensuring the output and quality of agricultural products and ensuring human food security. High-quality, low-toxic, low-residue, economical and easy-to-use pesticide varieties should be the direction of pesticide development.
  • Pesticide researchers have found the problem of adding organic solvents to pesticides. This is the problem of low solubility of pesticides, or that agricultural compounds are difficult to dissolve in water. This problem is prevalent in currently applied biological pesticides, biomimetic pesticides and chemical pesticides. Even new pesticides that have been on the market in recent years have not solved this problem.
  • pesticides are usually water as a dispersion medium, the usual method of use is to tens of times to thousands of times in the preparation of water on farmland, vegetable fields Orchard spray application. Therefore, the amount of solubility in water is a key factor in determining the efficacy of pesticides.
  • the most important pesticides widely used in today's pesticides are mostly poorly water-soluble drugs, which have to be added in large quantities. Adding organic solvents increases their solubility to achieve the purpose of improving the efficacy and controlling pests and diseases.
  • the avermectin has a solubility in water of about 10 ⁇ g/L; the ivermectin has a solubility in water of about 4 mg/L; the emamectin benzoate (a salt) is in the water.
  • Solubility is about 300mg / L; the solubility of azoxystrobin in water is about 6mg / L; the original drug of cyhalothrin is 0.004ppb (at 20 ° C) in solubility water, according to the classification of drug solubility, "almost Insoluble or insoluble refers to the definition that the solute 1 g (ml) cannot be completely dissolved in the solvent 10000 ml, and the original drugs of these drugs are all insoluble and almost insoluble types.
  • toxic organic solvents such as benzene, toluene and xylene of aromatic hydrocarbons are good solvents for these pesticides.
  • the avermectin has a solubility of up to 350 g/L in toluene, but only in water. 10 ⁇ g / L.
  • the avermectin preparation commonly used in pesticides is avermectin ointment, which is an accessory of avermectin refined powder, which is contained in xylene-dissolved emulsifiable concentrate, and the content is between 3 and 7%.
  • the main components of a lambda-cyhalothrin emulsion are: cyhalothrin 2.9%, methanol 20%, xylene 40%.
  • Liposomes may also leak and degenerate when they are loaded with drugs; they are only suitable for specific individual drugs, which are specific methods, and have no universality; various excipients, which bring more impurities and difficult quality control.
  • the main problem is that no suitable drug carrier has been found. material.
  • the existing traditional excipients are mostly solid granular, and there is no small-scale spatial structure for accommodating drugs. Most of them are loaded with drug molecules on the surface of the fine solid structure, so that a high drug loading amount cannot be achieved, and the formation is often the main Small-scale mixtures with low drug content and large amount of excipients are difficult to meet the basic requirements for high drug loading, large specific surface area and stable quality.
  • the present invention provides a pesticide preparation prepared by using silica aerogel and a preparation method thereof, and the technical problems of the present invention are as follows:
  • a method for preparing a pesticide preparation by using a silica aerogel wherein the application refers to a silica aerogel as a carrier for processing a nanometer preparation of a poorly soluble crude drug, and the processing steps are as follows:
  • silica aerogel using a silica aerogel to adsorb a solvent-containing liquid containing a drug solvent or mixing the pulverized original drug to form a nanoparticle drug-loading system having a diameter of less than 100 nm, the silica aerogel being hydrophilic
  • the silica aerogel or the hydrophobic silica aerogel has a hydrophilic silica aerogel after heat treatment, and the mass ratio of the pesticide original drug to the silica aerogel is 1:0.5-20,
  • the silica aerogel encapsulates the drug molecule in its nano-network structure to form a stable nano-solid dispersion of the drug.
  • the drug aqueous agent formed by the multi-fold water is transparent and has little precipitation, and The comparison of the equivalent water amount of several commercial preparations shows that the pesticide preparation prepared by the method of the invention has the least precipitation and the longest stabilization time;
  • the nanoparticle drug delivery system is uniformly dispersed with water; after this step is completed, a liquid product that can be applied has been formed.
  • the pesticide of the product can be directly diluted with water before application.
  • the pesticide is one or more selected from the group consisting of insoluble insecticides, bactericides, and herbicides.
  • the insecticide is selected from the group consisting of pyrethroids, carbamates, organic phosphorus, organic sulfur, organic choline, silkworm toxin, neonicotinoid, phenyl acyl urea, avermectin, and emamectin benzene.
  • Acid salt bismuth, cockroach, phenylpyrazole, indoxacarb or dibutyl ether urea insecticide;
  • the bactericide is selected from the group consisting of anilinopyridine, antibiotics, aromatic hydrocarbons, dinitroaniline, azoxystrobin, allylamine, benzenesulfonamide, benzimidazole, benzisothiazole, benzophenone, benzoyl Pyrimidine, benzotriazine, benzyl carbamate, carbamate, carboxamide, carboxylic acid diamide, chloronitrile, cyanoimidazole, cyclopropanecarboxamide, ethylaminothiazole carboxamide, imidazole, hydroxyanilide , imidazolinone, isobenzofuranone, methoxy acrylate, methoxy carbamate, morpholine, N-phenyl carbamate, oxazolidinedione, phenylacetamide, phenyl Amide, phenylpyrrole, phenylurea, phosphorothioate, o-
  • the herbicide is selected from the group consisting of an amide, an aryloxyphenoxypropionate, a phenoxycarboxylic acid, an organophosphorus, a benzamide, a benzofuran, a benzoic acid, a benzothiadiazinone, a carbamate, Chloroacetamide, pyridine carboxylic acid, chlorocarboxylic acid, cyclohexanedione, dinitroaniline, diphenyl ether, isoxazole, isoxazolidinone, N-phenylphthalimide, malignant Azole, oxazolidinedione, oxyacetamide, phenylcarbamate, phenylpyridazine, sulfoaminocarboxytriazolinone, sulfonyltriazolocarbamide, triazolopyrimidine, triketone, Uracil or urea herbicide;
  • silica aerogel is a novel nano-material with three-dimensional network structure, which has a particle size scale of less than 100 nanometers strictly defined by materials science, and an independent spatial structure of less than 100 nanometers. With a thickness of 10,000 nanopores per millimeter, the volume of space (air) that can be used for drug loading is over 90%, which can reach the highest drug loading rate in history. It has a large specific surface area and a stable nano-aperture necessary for improving the bioavailability of the drug to improve the efficacy of the drug, and can be nano-dispersed and loaded with drugs by means of "self-assembly" and "cross-linking".
  • silica aerogel is a new type of microstructured porous material. Using this material as a pharmaceutically acceptable carrier can realize the “nanocrystallization” of the original drug from the mesoscale physical level without destroying the molecular structure of the original drug.
  • the silica molecule aerogel encapsulates the drug molecule and physically disperses it to maintain and fully exert its original biological activity. It reflects the characteristics of small scale, high surface activity and high bioavailability, which is difficult to achieve in traditional preparations. Since this principle has universal significance, the inventors believe that a variety of pesticides can be used to prepare new nanomedicine preparations, silica aerogels, which are convenient, fast, high-quality and low-cost.
  • the drug-loading material is a technique of commonality for the nano-treatment of most poorly soluble raw materials.
  • step 4 the nanomedicine is passed through a 100 mesh to 200 mesh sieve, and in the nanopesticide final product, it is most suitable to stabilize the properties of the solid nanoformulation in a micron-sized dispersion because the fine particles are too fine. It is easy to cause dusty flying, which is not conducive to field application. It is a good choice to pass the 200 mesh or even 100 mesh mesh particles by the preparation method of this patent, because the drug nanoparticles coated by these coarse particles are in contact with water. It can be quickly decomposed, does not affect the use, and greatly reduces dust during use.
  • the temperature of the heat treatment is 300 to 1000 °C.
  • silica aerogel as a carrier material has unique technical advantages in the processing of nanometer preparations for poorly soluble prodrugs.
  • Silica aerogel as the inorganic material itself has chemical inertness and physical stability, which reflects the high bio-inert and temperature stability of the organic carrier material and the stability of the finished structure.
  • the water-soluble drug is very low in water, but It has good high temperature performance and can be decomposed and deactivated at higher temperatures.
  • the melting point of the original avermectin is: 150-155 ° C; the melting point of the crude salt of the methicillin is 141-146 ° C, suggesting that the preparation process can be carried out at a higher temperature.
  • the original drug solution is adsorbed by the silica aerogel, it is not necessary to use an expensive high-pressure homogenizer when performing the dispersion treatment, and the ordinary stirring device can be used because the silica aerogel has utilized its own nano-scale.
  • the drug-loading space automatically and highly accurately physically disperses and isolates the contained drug.
  • the drug is dried, and it is not necessary to perform low-temperature drying or freeze-drying.
  • the silica aerogel has a porosity of 95 to 99%, a pore diameter of 10 to 50 nm, a specific surface area of 200 to 1000 m 2 /g, a density of 3 to 300 kg/m 3 , and colloidal particles constituting the network.
  • the diameter is 1 to 50 nm.
  • the solvent is ethanol or ethyl acetate, and since ethanol or ethyl acetate is low in toxicity, it is more environmentally friendly.
  • the drying method comprises drying, lyophilizing and spray drying, the drying temperature is 60 ° C to 120 ° C; the lyophilization temperature is -50 ° C to -70 ° C, the pressure is 0.1 to 10 Pa; and the drying temperature is 120. °C ⁇ 220 ° C, the inventors further research found that because the pesticide is poorly soluble original drug and silica aerogel both have good heat resistance, directly use ordinary drying equipment, such as ordinary oven can get nano
  • the bulk precursor of the dried drug body can be obtained by using a common pulverizing and sieving machine to obtain nanometer-sized drug dispersions of different particle sizes, meeting the quality requirements of the pesticide products and meeting the application requirements.
  • the nanomedicine finally obtained by the processing technology can reach a specific surface area of 300 m 2 /g. When a spray dryer is used, a microspherical nanosolid dispersion is obtained with a specific surface area of 300 m 2 /g.
  • the pesticide preparation is a nano-scale pesticide solid dispersion, a suspension preparation and a water agent, and there is no difference in stability between the micro-powder and the micro-spherical nano-scale pesticide solid dispersion, and the finished product is bottled or bagged. No desiccant, no reunion for more than three years. There is no difference in the application of the two traits.
  • the carrier material is a hydrophilic silica aerogel, which is a water-soluble carrier.
  • the finished product can be highly uniformly dispersed with a little stirring with water.
  • the liquid solution with high water added before application is water-like transparent.
  • the silica aerogel drug delivery system exhibits a high degree of physical stability, and the pesticide nanosolid dispersion is a powder, a tablet, a granule or a microcapsule.
  • Nano-medicine prepared by using silica aerogel the nano drug has a drug loading of >50%; encapsulation efficiency of >90%; drug-loaded microsphere specific surface area >300 m 2 /g; drug-loaded microspheres
  • the diameter is less than 5 ⁇ m, which can cover many kinds of original drug particles; stability investigation, no agglomeration time>3 years, there is no precedent for such preparations in international and domestic.
  • the present invention has the following advantages:
  • the present invention finds a new nano-carrier material for the pesticide preparation, which is not a popular nano-particle material or nano-powder, but truly realizes a nano-scale drug-loading hole new structure. It achieves the physical drug loading standard of less than 100 nanometers that can be realized by any material in today's medicinal materials, and fills the blank of carrier materials for nanometer-level pesticides in the world. It is universally applicable as a formulation innovation for many kinds of pesticides. sexual meaning.
  • a new pesticide preparation prepared by the present invention which does not contain an organic solvent, particularly benzene. It is of great practical significance to improve the quality of agricultural products, ensure food safety and protect the ecological environment and reduce environmental pollution.
  • the nano pesticide preparation prepared by the invention solves the technical problem that the poorly soluble original drug has to use an organic solvent to disperse the original drug because the solubility is too low.
  • This patent only uses B when preparing nano pesticide formulations.
  • a low-toxic or non-toxic organic solvent such as ethyl acetate or ethanol is used as a drug for dissolving the original drug, and the organic solvent is removed in a subsequent drying process to obtain a commercial drug containing no organic solvent.
  • an organic solvent particularly an aromatic hydrocarbon solvent, is added to the preparation of the preparation. These solvents are sold with commercial drugs and used on crops.
  • Figure 1 is an electron micrograph of a silica aerogel material, from which the nanoscale spatial structure of the silica aerogel can be seen;
  • the particle size of the pesticide dispersion prepared by the present invention is 25 nm;
  • FIG. 3 is an electron micrograph of drug-loaded microspheres prepared by using silica aerogel as a carrier. It can be seen that the drug-loaded microspheres prepared by the invention have a particle size of less than 2 ⁇ m, and the drug-loaded microspheres carry a large number of nano-sized drug particles.
  • the emulsion was dried using a dry box, parameters: temperature 100 ° C, time 12 hours.
  • the semi-finished product is pulverized through a 200 mesh sieve to obtain a nano-avermectin powder.
  • the obtained drug-loaded body was placed in a beaker, and 2000 ml of purified water was added and stirred.
  • the emulsion was dried using a dry box, parameters: temperature 120 ° C, time 12 hours.
  • the semi-finished product is pulverized through a 200 mesh sieve to obtain a nano-methyl avermectin benzoate powder.
  • the obtained drug-loaded body was placed in a beaker, and 2000 ml of purified water was added and stirred.
  • the emulsion was dried using a dry box, parameters: temperature 120 ° C, time 12 hours.
  • the semi-finished product is pulverized through a 200 mesh sieve to obtain nano ivermectin powder.
  • the emulsion was dried using a dry box, parameters: temperature 80 ° C, time 12 hours.
  • the semi-finished product is pulverized through a 200 mesh sieve to obtain a nanozoxystrobin powder.
  • the obtained drug-loaded body was placed in a beaker, and 2000 ml of purified water was added and stirred.
  • the emulsion was dried using a dry box, parameters: temperature 120 ° C, time 12 hours.
  • the semi-finished product is pulverized through a 200 mesh sieve to obtain a nano-methyl avermectin benzoate powder.
  • the obtained drug-loading body was placed in a beaker, and 2000 ml of purified water was added.
  • the emulsion was dried using a dry box, parameters: temperature 100 ° C, time 12 hours.
  • the semi-finished product is pulverized through a 150 mesh sieve to obtain a nanometer high-efficiency cyfluthrin powder.
  • the obtained drug-loading body was placed in a beaker, and 2000 ml of purified water was added.
  • the semi-finished product is pulverized through a 200 mesh sieve to obtain a nano-avermectin powder.
  • the obtained drug-loaded body was placed in a beaker, and 2000 ml of purified water was added and stirred.
  • the semi-finished product is pulverized through a 200 mesh sieve to obtain a nano-methyl avermectin benzoate powder.
  • the obtained drug-loaded body was placed in a beaker, and 2000 ml of purified water was added and stirred.
  • the semi-finished product is pulverized through a 200 mesh sieve to obtain nano ivermectin powder.
  • the obtained drug-loading body was placed in a beaker, and 2000 ml of purified water was added.
  • the semi-finished product is pulverized through a 200 mesh sieve to obtain a nanometer high-efficiency cyfluthrin powder.
  • the semi-finished product is pulverized through a 200 mesh sieve to obtain a nanozoxystrobin powder.
  • the obtained drug-loading body was placed in a beaker, and 2000 ml of purified water was added.
  • the obtained drug-loaded body was placed in a beaker, and 2000 ml of purified water was added and stirred.
  • the obtained drug-loaded body was placed in a beaker, and 2000 ml of purified water was added and stirred.
  • the obtained drug-loading body was placed in a beaker, and 2000 ml of purified water was added.
  • the nano-scale pesticide prepared by the invention has achieved satisfactory results in the field efficacy experiment, and the dosage forms used are all water-dispersible granules without organic solvent, which are obtained by the drying process in the examples provided by the patent.
  • the method of use is to spray after watering.

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  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne un procédé pour préparer une préparation de pesticide nanométrique à l'aide d'aérogel de silice. La présente invention se rapport au domaine technique des pesticides, et concerne plus particulièrement une application d'aérogel de silice comme nouveau porteur dans un adjuvant de pesticide. La solution technique est la suivante : l'invention concerne l'utilisation d'aérogel de silice comme porteur pour réaliser un traitement de préparation nanométrique sur une matière technique insoluble. Les étapes de traitement sont les suivantes : dissoudre une matière technique par un solvant ou écraser la matière technique ; charger le liquide contenant un solvant dans l'aérogel de silice au moyen d'absorption ou mélanger l'aérogel de silice avec la matière technique écrasée pour former un système de transport de pesticide de nanoparticule ayant une taille de particule inférieure à 100 nm ; ajouter de l'eau au système de transport de pesticide de nanoparticule, agiter ou émulsionner pour disperser uniformément le système de transport de pesticide de nanoparticule ; sécher pour éliminer le solvant et l'humidité de façon à obtenir le pesticide nanométrique. La présente invention présente les avantages d'être écologique et de remplir un espace de matière de porteur de pesticide nanométrique à la fois dans le pays et à l'étranger.
PCT/CN2015/093833 2015-11-05 2015-11-05 Procédé pour préparer une préparation de pesticide nanométrique à l'aide d'aérogel de silice WO2017075777A1 (fr)

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CN111170323A (zh) * 2020-02-26 2020-05-19 上海特栎材料科技有限公司 一种包裹/释放油性物质的二氧化硅气凝胶微球及其制备方法

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