CN115316389B - Preparation and application of diglycolate antibacterial agent - Google Patents

Preparation and application of diglycolate antibacterial agent Download PDF

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Publication number
CN115316389B
CN115316389B CN202210844781.7A CN202210844781A CN115316389B CN 115316389 B CN115316389 B CN 115316389B CN 202210844781 A CN202210844781 A CN 202210844781A CN 115316389 B CN115316389 B CN 115316389B
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diglycolate
copper
antibacterial
preparation
zinc
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CN115316389A (en
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季东鑫
唐宇琪
覃慧
金志敏
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Zhejiang University of Technology ZJUT
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Zhejiang University of Technology ZJUT
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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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
    • 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
    • A01N59/16—Heavy metals; Compounds thereof
    • 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
    • A01N59/16—Heavy metals; Compounds thereof
    • A01N59/20—Copper
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P3/00—Fungicides
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Abstract

The invention belongs to the technical field of antibacterial agents, in particular to preparation and application of a diglycolate antibacterial agent, and aims to provide the preparation and application of the antibacterial agent with diglycolate as an active ingredient. The diglycolic acid salt is prepared by the meridian combination reaction of diglycolic acid and copper salt or zinc salt. The diglycolate prepared by the invention has strong antibacterial effect, broad antibacterial spectrum and the like. Indoor toxicity tests prove that the invention has high-efficiency antibacterial effect on series of plant pathogenic bacteria strains such as wheat fusarium graminearum, fusarium moniliforme, camellia anthracnose and the like; the field efficacy test proves that the invention has good safety to crops such as wheat and the like and can be used as an antibacterial agent in agriculture.

Description

Preparation and application of diglycolate antibacterial agent
Technical field:
the invention belongs to the technical field of antibacterial agents, and particularly relates to preparation and application of an antibacterial agent with diethylene glycol acid copper salt or diethylene glycol acid zinc salt as active components. The purpose is to provide an agricultural antibacterial agent with strong antibacterial effect, broad antibacterial spectrum, low toxicity and high efficiency.
The background technology is as follows:
diglycolic acid, also called diglycolic acid, has the chemical formula: c (C) 4 H 6 O 5 Is a white crystal, and is mainly used for complexing agents, synthetic resins, manufacturing plasticizers, organic synthesis and the like.
The copper-based bactericide has the advantages of wide antibacterial spectrum and low drug resistance, has long use history and has larger proportion in the market. Copper preparations have been used as bactericides in agricultural production for over 200 years, and have not been degraded for a long time; the treatment of copper fungicides is generally aimed at reducing or inhibiting the occurrence of bacterial and fungal diseases of plants to increase crop yield.
Copper formulation development has so far been largely divided into inorganic copper and organic copper formulations. The inorganic copper preparation belongs to a protective bactericide, the active ingredient is an inorganic copper compound, the preparation has the problem of difficult biodegradation, soil functions and plant growth environments are easy to cause after long-term use, the preparation is generally ineffective to diseases which are invaded in a latent period, and the preparation needs to be applied before bacteria invade, so that the preparation has a preventive and protective effect. The organic copper preparation is usually prepared from organic copper compounds with stable single or complex structure as main active ingredients, and is mostly prepared from bivalent copper ions and chelating agents through chelating reaction, and has the characteristics of low copper content, biodegradability, low toxicity, environmental protection, high efficiency and the like.
The zinc-based bactericide has the same bactericidal capacity as silver and copper, and can achieve the efficient bactericidal effect by only using trace amount. Zinc-based bactericides not only exhibit excellent antimicrobial properties against both gram-negative and gram-positive bacteria, but also have a certain selection preference for their resistance to eukaryotic and prokaryotic organisms. Researchers have found that zinc-based bactericides have very little effect on immune-competent human T cells when the concentration of the bactericides increases to a level that kills harmful bacteria such as staphylococcus aureus, escherichia coli, and the like.
There are two sterilization mechanisms for zinc ions: firstly, zinc ions can be used as an active catalytic center to excite oxygen in water or air to generate hydroxyl free radicals and active oxygen ions, so that oxidative stress reaction is generated, the reproductive capacity of bacteria is destroyed, and the bacteria die; secondly, zinc ions are positively charged, when excessive zinc ions reach the surface of bacteria, because the cell membrane carries negative charges, the zinc ions can be firmly adsorbed on the surface of the cell membrane by virtue of coulomb force and further penetrate through the cell wall, so that the cell wall is broken, the cell cytoplasm is caused to outflow, the cell reproduction is hindered, and the bacterial death is finally caused.
At present, the preparation of the copper diglycolate and the zinc diglycolate and the application of the copper diglycolate and the zinc diglycolate in agriculture have not been reported.
The invention comprises the following steps:
the invention aims to provide a preparation and application of an antibacterial agent with diethylene glycol acid copper salt or diethylene glycol acid zinc salt as active components, and aims to provide an agricultural antibacterial agent with strong antibacterial effect, broad antibacterial spectrum, low toxicity and high efficiency, which is used for preventing and treating plant diseases.
In order to achieve the purpose of the invention, the technical scheme of the invention is as follows:
the antibacterial agent of the invention takes copper diglycolate or zinc diglycolate as an active ingredient;
the preparation formulation of the antibacterial agent can be aqueous emulsion, wettable powder, water dispersible granules, suspending agents, granules or emulsifiable concentrates;
preferably, the antibacterial agent of the invention is in the form of a suspension;
the suspending agent disclosed by the invention takes copper diglycolate as an active ingredient and is prepared from the following components in percentage by mass: 0.5 to 90 percent of diglycol cupric acid salt, 0.5 to 5 percent of defoaming agent, 0.5 to 10 percent of wetting dispersant, 0.5 to 10 percent of surfactant, 0.5 to 10 percent of antifreezing agent, 0.5 to 10 percent of thickening agent, 0.5 to 10 percent of stabilizer, 0.5 to 10 percent of solubilizer and the balance of deionized water;
the suspending agent disclosed by the invention takes zinc diglycolate as an active ingredient and is prepared from the following components in percentage by mass: 0.5 to 90 percent of zinc diglycolate, 0.5 to 5 percent of defoamer, 0.5 to 10 percent of wetting dispersant, 0.5 to 10 percent of surfactant, 0.5 to 10 percent of antifreeze, 0.5 to 10 percent of thickener, 0.5 to 10 percent of stabilizer, 0.5 to 10 percent of solubilizer and the balance of deionized water;
the suspending agent comprises one or more auxiliary components selected from defoamer, wetting dispersant, surfactant, antifreezing agent, solubilizer and thickener;
the suspending agent disclosed by the invention adopts the following auxiliary agents: the wetting dispersant in the preparation is one or more of sodium sulfonate, sodium polycarboxylate, fatty acid block polyether and polyvinyl alcohol monooleate; the thickener is one or more of glycerol, xanthan gum, magnesium aluminum silicate, polyvinyl alcohol and hydroxymethyl cellulose; the stabilizer is white carbon black; the antifreezing agent is one or more of ethylene glycol, propylene glycol, glycerol, ethylene glycol butyl ether and ethylene glycol butyl ether acetate; the defoamer is polyether modified silicon;
the suspending agent is used for preventing and treating plant diseases.
The accompanying drawings:
fig. 1: diethylene glycol copper salt infrared spectrum
Fig. 2: zinc diglycolate infrared spectrum spectrogram
The specific embodiment is as follows:
the invention will be further described with reference to specific examples, but the scope of the invention is not limited thereto:
it should be understood that these examples are preferred embodiments of the invention and are presented for purposes of illustration only. From the foregoing discussion and these examples, one skilled in the art can ascertain the essential characteristics of this invention, and without departing from the spirit and scope thereof, can make various changes and modifications of the invention to adapt it to various usages and conditions.
The copper acetate and zinc acetate of the embodiment of the invention are purchased from Shandong Asahi photochemical Co., ltd; the 40% copper quinoline (CAS: 10380-28-6) suspension was purchased from Huinong chemical Co., ltd; the difference caused by raw material batches is avoided, and the average difference of the dissolution rates of the products produced by different batches is less than or equal to 0.05%.
The test agents adopted in the embodiment of the invention are as follows: 20% of a copper diglycolate suspending agent and 20% of a zinc diglycolate suspending agent; the control agent used was 20% zinc glycolate suspension, 20% copper glycolate suspension, 40% copper quinoline suspension. The preparation process is as follows:
example 1:
1. the formula (weight portions):
20 parts of diglycolic acid, 20 parts of copper acetate, 3 parts of fatty alcohol polyoxyethylene ether phosphate, 2 parts of nonylphenol polyoxyethylene ether phosphate, 0.2 part of xanthan gum, 2 parts of glycerol, 0.3 part of polyether modified silicon and the balance of deionized water.
2. The preparation method comprises the following steps:
(1) And (3) preparation: adding 20kg of diglycolic acid and 20kg of copper acetate into a stirring reaction kettle, adding 150L of water, stirring and reacting for 30min at a reaction temperature of 60 ℃, and obtaining blue precipitate which is the copper diglycolate salt;
(2) And (3) filtering: filtering and drying the prepared diglycol acid copper salt to obtain a product, wherein the infrared spectrogram of the product is shown in figure 1;
(3) Mixing: mixing 20% of copper diglycolate, 3% of fatty alcohol polyoxyethylene ether phosphate, 2% of nonylphenol polyoxyethylene ether phosphate, 2% of glycerol and 0.3% of polyether modified silicon, supplementing the balance with water, and stirring for 30min to obtain a mixed material;
(4) Grinding: transferring the mixed materials into a sand mill, grinding for 1h at a high speed of 2500r/min at room temperature, and grinding the mixed materials until the average particle size is smaller than 3 mu m to obtain a sand-ground material;
(5) Shearing: adding the sand grinding material into an open cup, carrying out high shearing, adding 0.2% of xanthan gum under stirring, and shearing until the viscosity is 300-1000 mpa.s, thus obtaining 20% of copper diglycolate suspending agent.
Example 2:
1. the formula (weight portions):
20 parts of diglycolic acid, 20 parts of zinc acetate, 3 parts of fatty alcohol polyoxyethylene ether phosphate, 2 parts of nonylphenol polyoxyethylene ether phosphate, 0.2 part of xanthan gum, 2 parts of glycerol, 0.3 part of polyether modified silicon and the balance of deionized water.
2. The preparation method comprises the following steps:
(1) And (3) preparation: adding 20kg of diglycolic acid and 20kg of zinc acetate into a stirring reaction kettle, adding 150L of water, stirring and reacting for 30min at a reaction temperature of 60 ℃, wherein the obtained white precipitate is the zinc diglycolate;
(2) And (3) filtering: filtering and drying the prepared zinc diglycolate to obtain a product, wherein an infrared spectrogram of the product is shown in figure 2;
(3) Mixing: mixing 20% of zinc diglycolate, 3% of fatty alcohol polyoxyethylene ether phosphate, 2% of nonylphenol polyoxyethylene ether phosphate, 2% of glycerol and 0.3% of polyether modified silicon, supplementing the balance with water, and stirring for 30min to obtain a mixed material;
(4) Grinding: transferring the mixed materials into a sand mill, grinding for 1h at a high speed of 2500r/min at room temperature, and grinding the mixed materials until the average particle size is smaller than 3 mu m to obtain a sand-ground material;
(5) Shearing: adding the sand grinding material into an open cup, carrying out high shearing, adding 0.2% of xanthan gum under stirring, and shearing until the viscosity is 300-1000 mpa.s, thus obtaining 20% of zinc diglycolate suspending agent.
Comparative example 1:
1. the formula (weight portions):
20 parts of zinc glycolate (CAS: 18919-61-4), 3 parts of fatty alcohol polyoxyethylene ether phosphate, 2 parts of nonylphenol polyoxyethylene ether phosphate, 0.2 part of xanthan gum, 2 parts of glycerol, 0.3 part of polyether modified silicon and the balance of deionized water.
2. The preparation method comprises the following steps:
(1) Mixing: mixing 20% of zinc glycolate, 3% of fatty alcohol polyoxyethylene ether phosphate, 2% of nonylphenol polyoxyethylene ether phosphate, 2% of glycerol and 0.3% of polyether modified silicon, supplementing the balance with water, and stirring for 30min to obtain a mixed material;
(2) Grinding: transferring the mixed materials into a sand mill, grinding for 2 hours at a high speed of 2500r/min at room temperature, and grinding the mixed materials until the average particle size is smaller than 3 mu m to obtain a sand-ground material;
(3) Shearing: adding the sand grinding material into an open cup, carrying out high shearing, adding 0.2% of xanthan gum under stirring, and shearing until the viscosity is 300-1000 mpa.s, thus obtaining the 20% zinc glycolate suspending agent.
Comparative example 2:
1. the formula (weight portions):
20 parts of copper glycolate (CAS: 18911-01-8), 3 parts of fatty alcohol polyoxyethylene ether phosphate, 2 parts of nonylphenol polyoxyethylene ether phosphate, 0.2 part of xanthan gum, 2 parts of glycerol, 0.3 part of polyether modified silicon and the balance of deionized water.
2. The preparation method comprises the following steps:
(1) Mixing: mixing 20% of copper glycolate, 3% of fatty alcohol polyoxyethylene ether phosphate, 2% of nonylphenol polyoxyethylene ether phosphate, 2% of glycerol and 0.3% of polyether modified silicon, supplementing the balance with water, and stirring for 30min to obtain a mixed material;
(2) Grinding: transferring the mixed materials into a sand mill, grinding for 2 hours at a high speed of 2500r/min at room temperature, and grinding the mixed materials until the average particle size is smaller than 3 mu m to obtain a sand-ground material;
(3) Shearing: adding the sand grinding material into an open cup, carrying out high shearing, adding 0.2% of xanthan gum under stirring, and shearing until the viscosity is 300-1000 mpa.s, thus obtaining the 20% copper glycolate suspending agent.
Example 3 antibacterial Activity test
The experimental object: fusarium graminearum, fusarium moniliforme, and colletotrichum camellia anthracis
The experimental method comprises the following steps: oxford cup method
The experimental steps are as follows:
(1) Preparing a solution with the concentration of 50ppm by using 10g of the test agent and the control agent with sterilized water, and carrying out parallel experiments for 5 times by additionally setting the sterilized water as a blank control;
(2) The oxford cup is clamped by a sterilizing forceps and is uniformly placed in a bacteria-containing flat-plate culture medium (the pathogen OD600 is between 0.30 and 0.36, and the pathogen content is about 10) 9 cfu/ml)；
(3) Filling 0.1ml of test reagent into the cup by using a pipetting gun, and culturing for 2 days at 37 ℃;
(4) Taking out the culture medium, and measuring the diameter of the inhibition zone by using a crisscross method.
The antibacterial activity of the test agent and the control agent is examined by measuring the diameter of the inhibition zone, and the experimental results are shown in table 1:
TABLE 1 average antibacterial circle diameter (mm) for antibacterial experiments
Test agent Fusarium graminearum Fusarium moniliforme (L.) Reng Camellia anthracnose pathogen
20% zinc diglycolate suspension 26.8mm 29.6mm 28.0mm
20% copper diglycolate suspending agent 41.4mm 37.5mm 40.3mm
20% zinc glycolate suspending agent 16.1mm 17.3mm 19.4mm
20% copper glycolate suspending agent 28.3mm 31.6mm 34.9mm
40% quinoline copper suspending agent 32.7mm 30.3mm 31.6mm
Sterile water / / /
Note that: diameter of inhibition zone (mm) =outer diameter of inhibition zone (mm) -outer diameter of oxford cup (mm)
The antibacterial zone is less than 10mm, and has no antibacterial effect; a bacteriostasis zone of more than 10mm and less than 15mm is a moderate bacteriostasis effect; the inhibition zone is more than 15mm, and has high inhibition effect.
As shown in Table 1, aiming at fusarium graminearum, fusarium moniliforme and camellia anthracis, the average inhibition zone diameters of the 20% copper diglycolate suspending agent provided by the invention are respectively as follows: 41.4mm, 37.5mm and 40.3mm are all highly bacteriostatic, and compared with 20% of copper glycolate suspending agent and 40% of copper quinolinolate suspending agent, the copper quinolinolate suspending agent has obvious improvement. Meanwhile, the bacteriostatic activity of the 20% zinc diglycolate suspending agent is obviously improved compared with that of the 20% zinc glycolate suspending agent.
Example 4, 20% diglycolate suspension agent wheat safety assay
The method takes 20% of copper diglycolate suspending agent and 20% of zinc diglycolate suspending agent as test agents, and selects 3 different wheat varieties (Yumai 34, zhongyou 9507 and Zhongmai 9) to carry out a field wheat safety test. The specific operation steps are as follows:
(1) The test sample of the test reagent, namely 20% of the copper diglycolate suspending agent and 20% of the zinc diglycolate suspending agent, is diluted by tap water, and the test dosage of the test sample is set to be 6.25 g/mu, 12.5 g/mu and 25.0 g/mu of the active ingredient.
The wheat was sprayed at the test dose using the spray method. Every 12 wheat plants are treated, and the spraying of the pesticide is uniform to leaf surfaces. When the medicament is treated, the uniform and consistent spraying is ensured, and a blank control is additionally arranged. And (3) after treatment, performing conventional management, observing plant response symptoms at regular time, and recording phytotoxicity symptoms and phytotoxicity degrees, including discoloration, necrosis, growth and development conditions, deformity and the like. The heights of 12 wheat seedlings are measured at fixed points before the medicine is taken, the heights of the wheat seedlings are measured again after 25 days, the average growth length of the wheat seedlings is calculated, and the growth rate inhibition rate is calculated. The specific test results of 20% copper diglycolate suspending agent are shown in Table 2, and the specific test results of 20% zinc diglycolate suspending agent are shown in Table 3.
TABLE 2 safety test results of wheat 25d after 20% copper diglycolate suspending agent
Note that:
the test result shows that the 20% copper diglycolate suspending agent of the test agent has no influence on the growth of 3 wheat varieties of Yumai No. 34, zhongyou No. 9507 and Zhongmai No. 9 under the dosage of 6.25-25.0 g/mu of the active ingredient, and no symptoms such as malformation, yellowing, decay, necrosis and the like of wheat plants and leaves are observed, thus the 20% copper diglycolate suspending agent is safe to use on the test wheat.
Table 3, results of the wheat safety test 25d after 20% Zinc diglycolate suspending agent
Note that:
the test result shows that the 20% zinc diglycolate suspending agent of the test agent has no influence on the growth of 3 wheat varieties of Yumai No. 34, zhongyou No. 9507 and Zhongmai No. 9 under the dosage of 6.25-25.0 g/mu of the active ingredient, and no symptoms such as malformation, yellowing, decay, necrosis and the like of wheat plants and leaves are observed, thus the 20% zinc diglycolate suspending agent is safe to use on the test wheat.
In conclusion, the test shows that the diglycol acid copper salt or diglycol acid zinc salt bactericide prepared by the invention has stronger bactericidal effect compared with the glycolate bactericide and the quinoline copper, has obvious control effect on plant diseases such as wheat gibberella, fusarium moniliforme, camellia anthracnose and the like, and is safe to non-target crops such as wheat and the like without phytotoxicity. Therefore, the bactericide disclosed by the invention has obvious creative, inventive and use values.
The above embodiment is only a preferred embodiment of the present invention, and is not limited in any way, and any modifications, substitutions, improvements, etc. made on the basis of the present invention should be included in the scope of the present invention.

Claims (1)

1. Use of copper or zinc diglycolate for controlling fusarium graminearum, fusarium moniliforme or colletotrichum camellia anthracnose.
CN202210844781.7A 2022-07-09 2022-07-09 Preparation and application of diglycolate antibacterial agent Active CN115316389B (en)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101952372A (en) * 2007-12-21 2011-01-19 3M创新有限公司 Process for producing nanoparticles
CN104903758A (en) * 2013-02-19 2015-09-09 富士胶片株式会社 Near-infrared-absorbing composition, near-infrared cut-off filter using same, camera module, and manufacturing method therefor
CN109122687A (en) * 2018-08-25 2019-01-04 浙江工业大学 Glycollate complex fungicide and its application

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101952372A (en) * 2007-12-21 2011-01-19 3M创新有限公司 Process for producing nanoparticles
CN104903758A (en) * 2013-02-19 2015-09-09 富士胶片株式会社 Near-infrared-absorbing composition, near-infrared cut-off filter using same, camera module, and manufacturing method therefor
CN109122687A (en) * 2018-08-25 2019-01-04 浙江工业大学 Glycollate complex fungicide and its application

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