Nanogel drug-loading system based on tannin compound as well as preparation method and application of nanogel drug-loading system

Abstract

The invention relates to the technical field of pesticide preparations, in particular to a tannin compound-based nanogel drug delivery system as well as a preparation method and application thereof. The preparation method of the nanogel drug-loading system comprises the steps that a water phase containing a tannin compound and an oil phase containing a drug, modified epoxidized soybean oil and an emulsifier are emulsified, the nanogel drug-loading system is obtained, and the modified epoxidized soybean oil is obtained by modifying epoxidized soybean oil through an amino boric acid compound. The nanogel drug delivery system can realize intelligent release and efficient delivery, has good environmental friendliness and ecological safety, comprehensively solves the problems of low pesticide utilization rate, high environmental risk, single function, complex preparation and the like of the existing preparation, and has remarkable economic advantages.

Description

Technical Field

[0001] The present invention relates to the technical field of pesticide preparations, and in particular to a tannin compound-based nanogel drug-carrying system, a preparation method and an application thereof. Background Art

[0002] Traditional pesticide formulations suffer from issues such as susceptibility to photolysis of active ingredients, significant losses from rainwater washout, and poor targeting, leading to low field utilization rates, wasted resources, and environmental pollution. Furthermore, conventional emulsifiable concentrate formulations, due to their extensive use of organic solvents, are prone to causing phytotoxicity and pose potential toxicity risks to non-target organisms. In recent years, nanocarrier technology has been used to improve pesticide performance, but it still faces bottlenecks such as poor biocompatibility of carrier materials, complex preparation processes, high costs, and limited functionality.

[0003] Therefore, developing a multifunctional nanogel drug delivery system based on the synergistic effect of natural compounds and modified bio-based materials, which is environmentally friendly, dual-responsive (pH / active oxygen), anti-scouring and low ecotoxicity, has become the key to improving the efficiency of pesticide utilization and reducing environmental risks. Summary of the Invention

[0004] The present invention aims to overcome the above-mentioned problems of the prior art and provide a tannin compound-based nanogel drug delivery system, its preparation method, and application. The nanogel drug delivery system is simple to prepare, can achieve intelligent release and efficient delivery, and has good environmental friendliness and ecological safety.

[0005] In order to achieve the above-mentioned objectives, the present invention provides, on the one hand, a method for preparing a nanogel drug delivery system, which comprises: emulsifying an aqueous phase containing a tannin compound with an oil phase containing a drug, modified epoxidized soybean oil and an emulsifier to obtain a nanogel drug delivery system, wherein the modified epoxidized soybean oil is obtained by modifying epoxidized soybean oil with an aminoboric acid compound.

[0006] The second aspect of the present invention provides a nanogel drug-carrying system obtained by the above preparation method.

[0007] The third aspect of the present invention provides an application of the above-mentioned nanogel drug-carrying system in pesticide formulations.

[0008] This invention achieves functional integration through molecular design, utilizing the synergistic effect of natural tannin compounds and modified bio-based materials to create a multifunctional nanogel drug delivery system. This comprehensively addresses the pain points of existing pesticide formulations, such as low utilization rate, high environmental risks, single function, and complex preparation, while also offering significant economic advantages. The nanogel drug delivery system of the present invention has the following advantages:

[0009] (1) Good environmental friendliness and biocompatibility: The encapsulation system is constructed by using natural tannin compounds (natural polyphenols) and modified epoxidized soybean oil (bio-based materials), which enables natural renewable raw materials to replace traditional petroleum-based carriers, with almost no impact on the environment and organisms.

[0010] (2) Intelligent responsive release mechanism: Based on the dynamic chemistry of boron ester bonds, a dual response mechanism of pH responsiveness and reactive oxygen species (ROS) responsiveness is realized to achieve precise targeted release of drugs, improve drug release efficiency and effective concentration, and reduce the frequency of drug administration.

[0011] (3) Excellent resistance to environmental loss: The nanogel structure can improve the UV protection factor and extend the half-life of the active ingredients of the drug; the superhydrophobic surface combined with the gel network can greatly improve the resistance to rain erosion. DETAILED DESCRIPTION

[0012] The endpoints of the ranges and any values disclosed herein are not limited to the precise ranges or values, and these ranges or values should be understood to include values close to these ranges or values. For numerical ranges, the endpoints of each range, the endpoints of each range and individual point values, and the individual point values can be combined with each other to obtain one or more new numerical ranges, which should be considered to be specifically disclosed herein.

[0013] On the one hand, the present invention provides a method for preparing a nanogel drug delivery system, which comprises: emulsifying an aqueous phase containing a tannin compound with an oil phase containing a drug, modified epoxidized soybean oil and an emulsifier to obtain a nanogel drug delivery system, wherein the modified epoxidized soybean oil is obtained by modifying epoxidized soybean oil with an aminoboric acid compound.

[0014] According to the present invention, in order to achieve better effects, preferably, the particle size of the nanogel drug delivery system is 80-350 nm, preferably 120-280 nm, for example, it can be 120 nm, 130 nm, 200 nm, 250 nm and 280 nm and any range therebetween.

[0015] According to the present invention, in order to improve the various properties of the nanogel drug delivery system, preferably, the tannin compound is selected from one or more of tannic acid, tara tannin, bayberry tannin, larch tannin, epigallocatechin, epicatechin, gallic acid, ellagic acid and hematoxylin.

[0016] Preferably, the content of the tannin compound in the aqueous phase is 0.2-5wt%, preferably 0.5-2wt%, for example, it can be 0.5wt%, 0.8wt%, 1wt%, 1.5wt% and 2wt% and any range therebetween.

[0017] According to the present invention, the preparation process of the aqueous phase may include, for example, adding the tannin compound into water, stirring and dissolving the tannin compound to obtain the aqueous phase.

[0018] According to the present invention, in order to obtain a better nanogel structure, preferably, the content of the drug in the oil phase is 5-40wt%, preferably 10-30wt%, for example, it can be 10wt%, 15wt%, 20wt%, 25wt% and 30wt% and the range of any value therebetween.

[0019] Preferably, the content of the modified epoxidized soybean oil in the oil phase is 10-60wt%, preferably 20-50wt%, for example, it can be 20wt%, 30wt%, 40wt%, 45wt% and 50wt% and any range therebetween.

[0020] Preferably, the content of the emulsifier in the oil phase is 1-30wt%, preferably 2-20wt%, for example, it can be 2wt%, 8wt%, 10wt%, 15wt% and 20wt% and any value therebetween.

[0021] According to the present invention, in order to better perform the emulsification treatment, preferably, the solvent of the oil phase is selected from one or more of xylene, cyclohexanone, dichloromethane, n-hexane, n-heptane and ethyl acetate, preferably one or more of dichloromethane, xylene and cyclohexanone.

[0022] According to the present invention, in order to achieve better synergy with tannin compounds, preferably, the preparation method of the modified epoxidized soybean oil includes: contacting and reacting the aminoboric acid compound with the epoxidized soybean oil to obtain the modified epoxidized soybean oil.

[0023] Preferably, the aminoboronic acid compound is selected from one or more of 3-aminophenylboronic acid, 4-aminophenylboronic acid and 2-aminophenylboronic acid, preferably 3-aminophenylboronic acid and / or 4-aminophenylboronic acid.

[0024] Preferably, the molar ratio of the epoxidized soybean oil to the aminoboric acid compound is 1:1-15, preferably 1:1-10, for example, it can be 1:1, 1:4, 1:6, 1:10 and any range therebetween.

[0025] Preferably, the solvent for the contact reaction is selected from one or more of xylene, cyclohexanone, dichloromethane, n-hexane, n-heptane and ethyl acetate, preferably one or more of dichloromethane, xylene and cyclohexanone.

[0026] Preferably, the amount of the solvent used in the contact reaction is 5-30 mL, preferably 5-15 mL, relative to 1 mmol of the aminoboronic acid compound, for example, 5 mL, 8 mL, 12 mL, 15 mL, and any range therebetween.

[0027] According to the present invention, in order to better carry out the contact reaction, preferably, the conditions of the contact reaction include: a temperature of 10-40°C and a time of 10-30h; more preferably, the conditions of the contact reaction include: a temperature of 20-30°C (for example, it can be a range of values such as 20°C, 25°C, 28°C and 30°C and any values therebetween), and a time of 10-20h (for example, it can be a range of values such as 10h, 12h, 16h and 18h and any values therebetween).

[0028] According to the present invention, in order to achieve better emulsification treatment effect, preferably, the emulsifier is selected from one or more of the Span series, Tween series, OP series, OX series, Nongru series and Ningru series, preferably one or more of Span-80, Tween-20, Tween-80, OP-10, OX-2656, Nongru-500, Nongru-Sorpol2678S, Nongru-1601, Nongru-0201B and Ningru-130.

[0029] According to the present invention, the drug can be selected from a wide range. In order to achieve better effects, preferably, the drug is selected from one or more of fungicides, herbicides, insecticides and acaricides and antivirals, preferably one or more of pyraclostrobin, azoxystrobin, difenoconazole, atrazine, mesotrione, avermectin, imidacloprid, bifenthrin and ningnanmycin.

[0030] According to the present invention, the preparation process of the oil phase may include, for example, adding the drug, the modified epoxidized soybean oil and the emulsifier into a solvent, and stirring and dissolving them to obtain the oil phase.

[0031] According to the present invention, in order to obtain a nanogel drug delivery system with better properties and performance, preferably, the weight ratio of the oil phase to the aqueous phase is 1:1-20, preferably 1:1-10, for example, it can be 1:2, 1:5, 1:8 and 1:10 and the range between any values.

[0032] Preferably, the shear rate of the emulsification treatment is 8000-25000 rpm, preferably 10000-20000 rpm, for example, it can be 10000 rpm, 15000 rpm, 18000 rpm, 20000 rpm and any range therebetween.

[0033] Preferably, the emulsification treatment time is 10-40 min, preferably 15-30 min, for example, it can be 15 min, 18 min, 20 min, 25 min, 30 min, and any range therebetween.

[0034] The second aspect of the present invention provides a nanogel drug-carrying system obtained by the above preparation method.

[0035] The third aspect of the present invention provides an application of the above-mentioned nanogel drug-carrying system in pesticide formulations.

[0036] The present invention achieves functional integration through molecular design, utilizing the synergistic effect of natural tannin compounds and modified bio-based materials to obtain a multifunctional nanogel drug delivery system, which comprehensively solves the pain points of existing pesticide formulations, such as low utilization rate, high environmental risks, single function, and complex preparation, and has significant economic advantages. The nanogel drug delivery system of the present invention has a 48-hour drug release rate of ≥80wt% under a pH of 5 environment (disease microenvironment), improves drug release efficiency in areas with overexpression of reactive oxygen species (lesion sites), and can extend the half-life of the active ingredient of the drug by 2-5 times. The encapsulation efficiency is high, and the drug residue rate after 50mm / h rainstorm is as high as 85wt% or more. It also has good wettability and extremely low ecotoxicity.

[0037] The present invention will be described in detail below through examples.

[0038] In the following examples, the devices used are all conventional experimental devices in this field, the experimental operations adopted are all conventional operations in this field, and the raw materials, reagents, etc. used can be obtained commercially.

[0039] Epoxidized soybean oil, taratannin, bayberry tannin, larch tannin, ellagic acid, epicatechin, hematoxylin, gallic acid, and OP-10 were purchased from Beijing Inokai. Tannic acid was purchased from Sigma. Pyraclostrobin, Span-80, azoxystrobin, Tween-80, Nongru-0201B, and Tween-20 were purchased from Shanghai Myril Biochemical Technology. Atrazine, Nongru-500, Ningru-130, difenoconazole, and Nongru-1601 were purchased from Xiens Biotechnology. Atrazine, Nongru-500, avermectin, Nongru-Sorpol 2678S, Ningnanmycin, mesotrione, bifenthrin, OX-2656, epigallocatechin, and imidacloprid were purchased from Shanghai Bid Pharmaceutical.

[0040] Example 1

[0041] (1) Epoxidized soybean oil and 3-aminophenylboronic acid were added to cyclohexanone in a molar ratio of 1:1, and the mixture was reacted at 25°C for 10 h to obtain 3-aminophenylboronic acid-modified epoxidized soybean oil, wherein the amount of cyclohexanone used was 5 mL relative to 1 mmol of 3-aminophenylboronic acid.

[0042] (2) Prepare a 1 wt% tannic acid aqueous solution as the aqueous phase.

[0043] (3) An oil phase was prepared with a pyraclostrobin content of 25 wt%, a 3-aminophenylboronic acid modified epoxy soybean oil content of 35 wt%, a Span-80 content of 10 wt%, and the balance being solvent cyclohexanone.

[0044] (4) The oil phase was slowly added to the water phase (the weight ratio of the oil phase to the water phase was 1:1), and emulsified at a shear rate of 15,000 rpm for 15 min to obtain a nanogel drug delivery system.

[0045] Example 2

[0046] (1) Epoxidized soybean oil and 3-aminophenylboronic acid were added to xylene in a molar ratio of 1:2 and reacted at 20°C for 12 h to obtain 3-aminophenylboronic acid-modified epoxidized soybean oil, wherein the amount of xylene used was 7.5 mL relative to 1 mmol of 3-aminophenylboronic acid.

[0047] (2) A 0.67 wt% taratanine aqueous solution was prepared as the aqueous phase.

[0048] (3) An oil phase was prepared with azoxystrobin content of 18 wt%, 3-aminophenylboronic acid modified epoxy soybean oil content of 40 wt%, Tween-80 content of 5 wt%, and the balance being solvent xylene.

[0049] (4) The oil phase was slowly added to the water phase (the weight ratio of the oil phase to the water phase was 1:2), and emulsified at a shear rate of 20,000 rpm for 20 min to obtain a nanogel drug delivery system.

[0050] Example 3

[0051] (1) Epoxidized soybean oil and 3-aminophenylboronic acid were added to dichloromethane in a molar ratio of 1:3 and reacted at 30°C for 16 h to obtain 3-aminophenylboronic acid-modified epoxidized soybean oil, wherein the amount of dichloromethane used was 10 mL relative to 1 mmol of 3-aminophenylboronic acid.

[0052] (2) Prepare a 1.3 wt% bayberry tannin aqueous solution as the aqueous phase.

[0053] (3) Prepare an oil phase with 28 wt% of atrazine, 30 wt% of 3-aminophenylboronic acid modified epoxy soybean oil, 8 wt% of Nongru-500, and the balance being solvent dichloromethane.

[0054] (4) The oil phase was slowly added to the water phase (the weight ratio of the oil phase to the water phase was 1:3), and emulsified at a shear rate of 12000 rpm for 25 min to obtain a nanogel drug delivery system.

[0055] Example 4

[0056] (1) Epoxidized soybean oil and 3-aminophenylboronic acid were added to ethyl acetate in a molar ratio of 1:4 and reacted at 25°C for 18 h to obtain 3-aminophenylboronic acid-modified epoxidized soybean oil, wherein the amount of ethyl acetate used was 15 mL relative to 1 mmol of 3-aminophenylboronic acid.

[0057] (2) A 0.5 wt% larch tannin aqueous solution was prepared as the aqueous phase.

[0058] (3) Prepare an oil phase with a content of 22 wt% of avermectin, 30 wt% of 3-aminophenylboronic acid modified epoxy soybean oil, 8 wt% of Nongru-Sorpol 2678S, and the balance being solvent ethyl acetate.

[0059] (4) The oil phase was slowly added to the water phase (the weight ratio of the oil phase to the water phase was 1:4), and emulsified at a shear rate of 20,000 rpm for 18 min to obtain a nanogel drug delivery system.

[0060] Example 5

[0061] (1) Epoxidized soybean oil and 3-aminophenylboronic acid were added to n-hexane at a molar ratio of 1:5 and reacted at 25°C for 16 h to obtain 3-aminophenylboronic acid-modified epoxidized soybean oil, wherein the amount of n-hexane used was 10 mL relative to 1 mmol of 3-aminophenylboronic acid.

[0062] (2) Prepare a 2 wt% ellagic acid aqueous solution as the aqueous phase.

[0063] (3) Prepare an oil phase with a Ningnanmycin content of 30 wt%, a 3-aminophenylboronic acid modified epoxy soybean oil content of 50 wt%, a Ningru-130 content of 2 wt%, and the remainder being solvent n-hexane.

[0064] (4) The oil phase was slowly added to the water phase (the weight ratio of the oil phase to the water phase was 1:5), and emulsified at a shear rate of 18,000 rpm for 20 min to obtain a nanogel drug delivery system.

[0065] Example 6

[0066] (1) Epoxidized soybean oil and 3-aminophenylboronic acid were added to n-heptane at a molar ratio of 1:6 and reacted at 25°C for 10 h to obtain 3-aminophenylboronic acid-modified epoxidized soybean oil, wherein the amount of n-heptane used was 7.5 mL relative to 1 mmol of 3-aminophenylboronic acid.

[0067] (2) A 0.83 wt% epicatechin aqueous solution was prepared as the aqueous phase.

[0068] (3) An oil phase was prepared with a content of 20 wt% of difenoconazole, a content of 40 wt% of 3-aminophenylboronic acid-modified epoxy soybean oil, a content of 2 wt% of OP-10, and the balance being solvent n-heptane.

[0069] (4) The oil phase was slowly added to the water phase (the weight ratio of the oil phase to the water phase was 1:6), and emulsified at a shear rate of 16,000 rpm for 22 min to obtain a nanogel drug delivery system.

[0070] Example 7

[0071] (1) Epoxidized soybean oil and 3-aminophenylboronic acid were added to ethyl acetate at a molar ratio of 1:7 and reacted at 25°C for 12 h to obtain 3-aminophenylboronic acid-modified epoxidized soybean oil, wherein the amount of ethyl acetate used was 5 mL relative to 1 mmol of 3-aminophenylboronic acid.

[0072] (2) Prepare a 1.7 wt% hematoxylin aqueous solution as the aqueous phase.

[0073] (3) Prepare an oil phase with a mesotrione content of 28 wt%, a 3-aminophenylboronic acid modified epoxy soybean oil content of 20 wt%, a Nongru-1601 content of 6 wt%, and the balance being solvent ethyl acetate.

[0074] (4) The oil phase was slowly added to the water phase (the weight ratio of the oil phase to the water phase was 1:7), and emulsified at a shear rate of 14,000 rpm for 25 min to obtain a nanogel drug delivery system.

[0075] Example 8

[0076] (1) Epoxidized soybean oil and 3-aminophenylboronic acid were added to n-hexane at a molar ratio of 1:8 and reacted at 25°C for 16 h to obtain 3-aminophenylboronic acid-modified epoxidized soybean oil, wherein the amount of n-hexane used was 5 mL relative to 1 mmol of 3-aminophenylboronic acid.

[0077] (2) Prepare a 0.56 wt% gallic acid aqueous solution as the aqueous phase.

[0078] (3) An oil phase was prepared with a content of 15 wt% of bifenthrin, 45 wt% of 3-aminophenylboronic acid-modified epoxy soybean oil, 18 wt% of OX-2656, and the remainder being solvent n-hexane.

[0079] (4) The oil phase was slowly added to the water phase (the weight ratio of the oil phase to the water phase was 1:7), and emulsified at a shear rate of 19000 rpm for 15 min to obtain a nanogel drug delivery system.

[0080] Example 9

[0081] (1) Epoxidized soybean oil and 3-aminophenylboronic acid were added to ethyl acetate in a molar ratio of 1:9 and reacted at 20°C for 18 h to obtain 3-aminophenylboronic acid-modified epoxidized soybean oil, wherein the amount of ethyl acetate used was 5 mL relative to 1 mmol of 3-aminophenylboronic acid.

[0082] (2) A 1.1 wt% epigallocatechin aqueous solution was prepared as the aqueous phase.

[0083] (3) Prepare an oil phase with an imidacloprid content of 25 wt%, a 3-aminophenylboronic acid modified epoxy soybean oil content of 20 wt%, a Nongru-0201B content of 5 wt%, and the balance being solvent ethyl acetate.

[0084] (4) The oil phase was slowly added to the water phase (the weight ratio of the oil phase to the water phase was 1:8), and emulsified at a shear rate of 17,000 rpm for 18 min to obtain a nanogel drug delivery system.

[0085] Example 10

[0086] (1) Epoxidized soybean oil and 3-aminophenylboronic acid were added to xylene in a molar ratio of 1:10 and reacted at 20°C for 12 h to obtain 3-aminophenylboronic acid-modified epoxidized soybean oil, wherein the amount of xylene used was 15 mL relative to 1 mmol of 3-aminophenylboronic acid.

[0087] (2) Prepare a 1 wt% tannic acid aqueous solution as the aqueous phase.

[0088] (3) An oil phase was prepared with a myclobutanil content of 15 wt%, a cypermethrin content of 10 wt%, a 3-aminophenylboronic acid-modified epoxy soybean oil content of 45 wt%, a Tween-20 content of 3 wt%, and the balance being solvent xylene.

[0089] (4) The oil phase was slowly added to the water phase (the weight ratio of the oil phase to the water phase was 1:9), and emulsified at a shear rate of 18,000 rpm for 20 min to obtain a nanogel drug delivery system.

[0090] Example 11

[0091] The method of Example 1 is different in that, in step (2), the concentration of the tannic acid aqueous solution is 0.2 wt %.

[0092] Example 12

[0093] The method of Example 1 is different in that, in step (2), the concentration of the tannic acid aqueous solution is 5 wt %.

[0094] Example 13

[0095] The method of Example 1 is different in that, in step (3), the content of 3-aminophenylboronic acid modified epoxidized soybean oil is 10 wt%.

[0096] Example 14

[0097] The method of Example 1 is different in that, in step (3), the content of 3-aminophenylboronic acid modified epoxy soybean oil is 60 wt%.

[0098] Example 15

[0099] The method of Example 1 is different in that in step (1), 3-aminophenylboronic acid is replaced by 4-aminophenylboronic acid.

[0100] Example 16

[0101] The method of Example 1 is different in that, in step (1), 3-aminophenylboronic acid is replaced by 2-aminophenylboronic acid.

[0102] Comparative Example 1

[0103] The method of Example 1 is different in that step (1) is not included and the 3-aminophenylboronic acid-modified epoxidized soybean oil in step (3) is replaced by epoxidized soybean oil.

[0104] Comparative Example 2

[0105] The method of Example 1 is the same as that of Example 1, except that the 1 wt % tannic acid aqueous solution in step (2) is replaced by deionized water as the aqueous phase.

[0106] Test Example 1

[0107] Encapsulation efficiency: The encapsulation efficiency of the nanogel drug delivery system was tested by high performance liquid chromatography.

[0108] Particle size: The particle size of the nanogel drug delivery system was measured by Mastersizer 3000 laser particle size analyzer.

[0109] Wettability: The leaf contact angle of the nanogel drug delivery system was tested using an OCA25 optical contact angle meter.

[0110] UV resistance: The half-life of the drug in the nanogel drug delivery system was tested by high performance liquid chromatography to reflect the UV resistance of the nanogel drug delivery system.

[0111] Anti-scouring property: The drug was washed under 10 mL / min simulated rainfall for 1-4 min, and the drug residual rate in the nanogel drug delivery system was tested by high performance liquid chromatography.

[0112] The test results are shown in Table 1.

[0113] Table 1

[0114]

[0115] Test Example 2

[0116] pH / ROS (pH / reactive oxygen species) responsiveness: The pH / ROS responsiveness of the nanogel drug delivery system was tested by high performance liquid chromatography.

[0117] Ecotoxicity: 130 rice seeds were evenly spread in a 10cm circular culture medium and soaked in a 100mg / L preparation solution. A sterile water treatment group was set as a control. The rice seed germination rate was calculated after 4 days. 8 zebrafish were placed in 2L solutions of different preparation concentrations. Pure water was set as a blank control group. After 96 hours, the median lethal concentration (96h LC) of zebrafish was 0.05. 50 ). The ecotoxicity of the nanogel drug delivery system to rice and zebrafish was tested.

[0118] The test results are shown in Table 2.

[0119] Table 2

[0120]

[0121]

[0122] As can be seen from Tables 1 and 2, the nanogel drug delivery systems obtained using Examples 1-16 of the present invention exhibit high encapsulation efficiency, good wettability, UV resistance, and rainwater resistance, as well as excellent pH / ROS responsiveness and ecocompatibility. The performance of the nanogel drug delivery systems obtained in Examples 1-16 is significantly superior to that of Comparative Examples 1-2.

[0123] The preferred embodiments of the present invention have been described in detail above, but the present invention is not limited thereto. Within the technical concept of the present invention, various simple variations of the technical solution of the present invention may be made, including combining the various technical features in any other appropriate manner. These simple variations and combinations should also be regarded as disclosed in the present invention and fall within the scope of protection of the present invention.

Claims

1. A method for preparing a nanogel drug delivery system, characterized in that: The method comprises: emulsifying an aqueous phase containing a tannin compound with an oil phase containing a drug, modified epoxidized soybean oil and an emulsifier to obtain a nanogel drug-carrying system, wherein the modified epoxidized soybean oil is obtained by modifying epoxidized soybean oil with an aminoboric acid compound.

2. The method according to claim 1, wherein The particle size of the nanogel drug delivery system is 80-350 nm, preferably 120-280 nm; and / or, the tannin compound is selected from one or more of tannic acid, tara tannin, myrica tannin, larch tannin, epigallocatechin, epicatechin, gallic acid, ellagic acid and hematoxylin; And / or, the content of the tannin compound in the aqueous phase is 0.2-5 wt%, preferably 0.5-2 wt%.

3. The method according to claim 1 or 2, wherein: The content of the drug in the oil phase is 5-40wt%, preferably 10-30wt%; And / or, the content of the modified epoxidized soybean oil in the oil phase is 10-60wt%, preferably 20-50wt%; And / or, the content of the emulsifier in the oil phase is 1-30 wt%, preferably 2-20 wt%.

4. The method according to any one of claims 1 to 3, wherein: The solvent of the oil phase is selected from one or more of xylene, cyclohexanone, dichloromethane, n-hexane, n-heptane and ethyl acetate, preferably one or more of dichloromethane, xylene and cyclohexanone.

5. The method according to any one of claims 1 to 4, wherein: The preparation method of the modified epoxidized soybean oil comprises: contacting and reacting the aminoboric acid compound with the epoxidized soybean oil to obtain the modified epoxidized soybean oil; Preferably, the aminoboronic acid compound is selected from one or more of 3-aminophenylboronic acid, 4-aminophenylboronic acid and 2-aminophenylboronic acid, preferably 3-aminophenylboronic acid and / or 4-aminophenylboronic acid; Preferably, the molar ratio of the epoxidized soybean oil to the aminoboric acid compound is 1:1-15, preferably 1:1-10; Preferably, the solvent for the contact reaction is selected from one or more of xylene, cyclohexanone, dichloromethane, n-hexane, n-heptane and ethyl acetate, preferably one or more of dichloromethane, xylene and cyclohexanone; Preferably, the amount of the solvent used in the contact reaction is 5-30 mL, preferably 5-15 mL, relative to 1 mmol of the aminoboronic acid compound; Preferably, the conditions for the contact reaction include: temperature of 10-40° C., and time of 10-30 h; more preferably, the conditions for the contact reaction include: temperature of 20-30° C., and time of 10-20 h.

6. The method according to any one of claims 1 to 5, wherein: The emulsifier is selected from one or more of the Span series, Tween series, OP series, OX series, Nongru series and Ningru series, preferably one or more of Span-80, Tween-20, Tween-80, OP-10, OX-2656, Nongru-500, Nongru-Sorpol2678S, Nongru-1601, Nongru-0201B and Ningru-130.

7. The method according to any one of claims 1 to 6, wherein: The drug is selected from one or more of fungicides, herbicides, insecticides and acaricides and antivirals, preferably one or more of pyraclostrobin, azoxystrobin, difenoconazole, atrazine, mesotrione, avermectin, imidacloprid, bifenthrin and ningnanmycin.

8. The method according to any one of claims 1 to 7, wherein: The weight ratio of the oil phase to the water phase is 1:1-20, preferably 1:1-10; and / or, the shear rate of the emulsification treatment is 8000-25000 rpm, preferably 10000-20000 rpm; And / or, the emulsification treatment time is 10-40 min, preferably 15-30 min.

9. The nanogel drug delivery system prepared by the method according to any one of claims 1 to 8.

10. Use of the nanogel drug delivery system according to claim 9 in pesticide preparations.

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