CN111567517B - Novel aqueous pesticide suspending agent and preparation method thereof - Google Patents
Novel aqueous pesticide suspending agent and preparation method thereof Download PDFInfo
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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
- A01N25/02—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 containing liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
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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
- A01N25/22—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 containing ingredients stabilising the active ingredients
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/707—1,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines
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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
- A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
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Abstract
The invention discloses a novel aqueous pesticide suspending agent and a preparation method thereof, belongs to the technical field of pesticides, and aims to solve the problems that the traditional pesticide suspending agent is easy to flocculate and agglomerate and has larger particles in the transportation and storage processes. The novel aqueous pesticide suspending agent prepared by the invention has the advantages of centrifugal stability of more than or equal to 80 percent, heat-resistant stability of more than or equal to 90 percent, simple production process, small equipment investment and stable product quality, and is suitable for industrial production.
Description
Technical Field
The invention relates to the technical field of pesticides, in particular to a novel aqueous pesticide suspending agent and a preparation method thereof.
Background
Agriculture is the foundation of national economy, pesticides occupy an extremely important position in the agricultural development process, but most of raw pesticides cannot be directly applied in agriculture and only need to be processed into pesticide preparations to enter the fields of downstream agriculture, forestry, animal husbandry, fishery, sanitation and the like; the pesticide water suspending agent gradually becomes one of the main development streams of pesticide preparations due to the advantages of safety, high efficiency, convenient production and application, good environmental compatibility and the like.
Under the action of wetting dispersant and other assistants, the traditional pesticide water suspending agent is prepared by uniformly dispersing original water-insoluble or water-insoluble pesticide in water by wet superfine grinding or coagulation to form a multiphase coarse suspension system with high suspension rate and good stability; however, in this method, a single molecule or a plurality of molecules such as a surfactant and a modifier are adsorbed on the surface of the original drug by van der waals force between the molecules of the original drug and various surfactants, and the dispersion stability of the suspending agent is liable to be undesirably changed depending on the change in external conditions (e.g., temperature, pH, etc.).
Most of raw pesticides are compounds with strong hydrophobicity, the application effect of the raw pesticides in plants or soil is directly influenced by the dispersion condition of the raw pesticides in an aqueous medium, the application aims to coat surfactant molecules containing carbon-carbon double bonds around the raw pesticides so as to carry out click chemical reaction, and the hydrophilic part in the surfactant is firmly fixed around the raw pesticides, so that the dispersion and the stability of the raw pesticides in the aqueous medium can be effectively improved. The key point of click chemistry is to complete the chemical synthesis of the molecules in different colors quickly and reliably through the splicing of small units. It is particularly emphasized that new combinatorial chemistry methods based on the synthesis of carbon-heteroatom bonds (C-X-C) are developed and that molecular diversity is obtained simply and efficiently by means of these reactions (click reactions). At present, reports of preparing pesticide suspending agents through chemical reactions are rare because part of raw pesticides are poor in heat-resistant stability and low in melting point of special raw pesticides, and the most common chemical reaction is to initiate free radicals through heating, so that the temperature becomes a limiting condition for the application of the method in the pesticide suspending agents.
Disclosure of Invention
The technical problem to be solved by the invention is to provide a novel aqueous pesticide suspending agent and a preparation method thereof, wherein a water-soluble compound containing sulfydryl (-SH) and carbon-carbon double bond (C ═ C) is used for carrying out click chemical reaction, and a light-catalyzed mode is adopted to graft a water-soluble functional group onto the surface of a raw pesticide molecule in a coating mode, so that the dispersion and the stability of the raw pesticide in an aqueous medium are improved.
In order to solve the technical problems, the technical scheme adopted by the invention is as follows:
a preparation method of a novel aqueous pesticide suspending agent comprises the steps of carrying out click chemical reaction on a water-soluble compound containing sulfydryl and carbon-carbon double bonds, and grafting a water-soluble functional group onto the surface of a raw pesticide molecule in a coating mode in a light irradiation catalysis mode; the method comprises the following steps:
(1) mixing the raw pesticide and a surfactant containing sulfydryl and carbon-carbon double bonds in a proportion of 1: 0.01: 0.01-1: 1: 1, adding the solvent in an amount which is 5-20 times of the amount of the original pesticide, uniformly mixing, and dispersing the original pesticide to micron level by sanding or shearing to prepare an aqueous solution dispersion system;
(2) adding an initiator accounting for 0.1-1% of the mass of the raw pesticide into the aqueous solution dispersion system, uniformly mixing, transferring the aqueous solution dispersion system into an ultraviolet illumination box for irradiating for 24 hours, and initiating a click reaction through ultraviolet irradiation;
(3) after the reaction is finished, adding the following components in an aqueous solution dispersion system according to mass percentage: uniformly mixing 1-5% of an antifreezing agent, 0.1-0.5% of a defoaming agent, 0.1-0.5% of a viscosity regulator and 0.1-2% of a stabilizer, and then sanding or shearing until the particle size reaches the micron level;
(4) and obtaining the novel aqueous pesticide suspending agent after the reaction is finished.
The technical scheme of the invention is further improved as follows: in the step (1), the pesticide raw material is one or two of emamectin benzoate, abamectin, spinosad, indoxacarb, pymetrozine, clothianidin, dinotefuran, imidacloprid, diflubenzuron, lambda-cyhalothrin, methoxyfenozide, chlorantraniliprole, etoxazole and spirodiclofen.
The technical scheme of the invention is further improved as follows: in the step (1), the mercapto-containing surfactant is one or two of 2-mercaptoethane sodium sulfonate, 2, 3-mercaptopropane sodium sulfonate, 3-mercapto-1-propane sodium sulfonate and 3- (benzothiazole-2-mercapto) propane sodium sulfonate; the surfactant containing carbon-carbon double bonds is one or two of sodium p-styrene sulfonate, sodium allyl sulfonate, sodium methyl propylene sulfonate and sodium cumene sulfonate.
The technical scheme of the invention is further improved as follows: the solvent used in the step (1) is water.
The technical scheme of the invention is further improved as follows: in the step (1) and the step (3), the sanding or shearing is a treatment mode of a high-speed dispersion machine, a sand mill, high-pressure micro jet and ultrasonic treatment.
The technical scheme of the invention is further improved as follows: in the step (2), the initiator is inorganic peroxide, and can be one or two of ammonium persulfate, sodium persulfate and potassium persulfate.
The technical scheme of the invention is further improved as follows: in the step (3), the antifreezing agent is one of ethanol, isooctanol and urea; the defoaming agent is an organic silicon defoaming agent; the viscosity regulator is one or two of xanthan gum, organic bentonite and polyethylene glycol; the stabilizer is magnesium aluminum silicate.
The technical scheme of the invention is further improved as follows: the solvent used in the step (1) is deionized water.
A novel aqueous pesticide suspending agent overcomes the defect that the original pesticide cannot resist high temperature, and has good dispersion effect in an aqueous medium.
Due to the adoption of the technical scheme, the invention has the technical progress that:
1. the invention carries out click chemical reaction by a water-soluble compound containing sulfydryl (-SH) and carbon-carbon double bond (C ═ C), adopts a light-catalyzed mode to graft a water-soluble functional group to the surface of a raw pesticide molecule in a coating mode, thereby improving the dispersion stability of the raw pesticide in an aqueous medium.
2. The click chemical reaction is utilized, water is used as a solvent, a water-soluble surfactant containing sulfydryl and carbon-carbon double bonds is adopted to sand or shear the original pesticide to obtain a temporary stable pre-dispersion, and then the click chemical reaction of the sulfydryl and the double bonds coated on the surface of the original pesticide is initiated in a form of illumination, so that a stable pesticide suspending agent is obtained; the prepared pesticide suspending agent has good dispersion effect in aqueous medium.
3. The invention coats the surface of the original pesticide by the surfactant through click chemical reaction, and then initiates the reaction in a lighting mode, so that the hydrophilic part in the surfactant is firmly fixed around the original pesticide, and the dispersion and the stability of the original pesticide in an aqueous medium can be effectively improved; the prepared pesticide suspending agent can overcome the defect that the original pesticide cannot resist high temperature on one hand, and can show good dispersion effect in a water phase and be dispersed in an aqueous medium to be ultra-stable on the other hand.
4. The novel pesticide suspending agent prepared by the invention has good dispersion stability in an aqueous medium: the centrifugal stability is more than or equal to 80 percent, and the heat-resistant stability is more than or equal to 90 percent.
5. The invention has simple production process, small equipment investment and stable product quality, and is suitable for industrial production.
Detailed Description
The invention provides a novel aqueous pesticide suspending agent and a preparation method thereof, which are developed aiming at the problems that the pesticide suspending agent is easy to flocculate and agglomerate and has larger particles in the transportation and storage processes.
The present invention will be described in further detail with reference to the following examples:
a preparation method of a novel aqueous pesticide suspending agent comprises the steps of carrying out click chemical reaction on a water-soluble compound containing sulfydryl and carbon-carbon double bonds, and grafting a water-soluble functional group onto the surface of a raw pesticide molecule in a coating mode in a light irradiation catalysis mode; the method comprises the following steps:
(1) mixing the raw pesticide and a surfactant containing sulfydryl and carbon-carbon double bonds in a proportion of 1: 0.01: 0.01-1: 1: 1, adding the solvent in an amount which is 5-20 times of the amount of the original pesticide, uniformly mixing, and dispersing the original pesticide to micron level by sanding or shearing to prepare an aqueous solution dispersion system;
the pesticide raw material is one or two of emamectin benzoate, abamectin, spinosad, indoxacarb, pymetrozine, clothianidin, dinotefuran, imidacloprid, diflubenzuron, high-efficiency cyhalothrin, methoxyfenozide, chlorantraniliprole, etoxazole and spirodiclofen;
the mercapto-containing surfactant is one or two of 2-mercaptoethane sodium sulfonate, 2, 3-mercaptopropane sodium sulfonate, 3-mercapto-1-propane sodium sulfonate and 3- (benzothiazole-2-mercapto) propane sodium sulfonate;
the surfactant containing carbon-carbon double bonds is one or two of sodium p-styrene sulfonate, sodium allyl sulfonate, sodium methyl propylene sulfonate and sodium cumene sulfonate;
the sanding or shearing adopts one of a high-speed dispersion machine, a sand mill, high-pressure micro jet and ultrasonic treatment.
The solvent used is water. The solvent used was deionized water.
(2) Adding an initiator accounting for 0.1-1% of the mass of the raw pesticide into the aqueous solution dispersion system, uniformly mixing, transferring the aqueous solution dispersion system into an ultraviolet illumination box for irradiating for 24 hours, and initiating a click reaction through ultraviolet irradiation;
the initiator is inorganic peroxide and can be one or two of ammonium persulfate, sodium persulfate and potassium persulfate.
(3) After the reaction is finished, adding the following components in an aqueous solution dispersion system according to mass percentage: uniformly mixing 1-5% of an antifreezing agent, 0.1-0.5% of a defoaming agent, 0.1-0.5% of a viscosity regulator and 0.1-2% of a stabilizer, and then sanding or shearing until the particle size reaches the micron level;
the antifreezing agent is one of ethanol, isooctanol and urea;
the defoaming agent is an organic silicon defoaming agent;
the viscosity regulator is one or two of xanthan gum, organic bentonite and polyethylene glycol;
the stabilizer is magnesium aluminum silicate.
The sanding or shearing adopts one of a high-speed dispersion machine, a sand mill, high-pressure micro jet and ultrasonic treatment.
(4) And obtaining the novel aqueous pesticide suspending agent after the reaction is finished.
A novel aqueous pesticide suspending agent can overcome the defect that the original pesticide cannot resist high temperature, and is ultra-stable to disperse in an aqueous medium.
The following are specific examples
Example 1
(1) Weighing 2kg of 2-mercaptoethane sodium sulfonate and 2kg of p-styrene sodium sulfonate, dissolving into 200kg of deionized water, stirring for 15min by using a stirrer, adding 40kg of dinotefuran raw drug after the surfactant is completely dissolved, and placing on a high-speed dispersion machine for dispersing for 2h to prepare an aqueous solution dispersion system;
(2) adding 1kg of ammonium persulfate into the aqueous solution dispersion system, continuously stirring for 15min, irradiating for 24h by adopting ultraviolet irradiation equipment under the condition of starting stirring, and initiating a click reaction by ultraviolet irradiation;
(3) after the reaction is finished, 6kg of ethylene glycol, 0.6kg of defoaming agent AF1500 (chemical industry in Guangzhou province, organic silicon defoaming agent), 0.2kg of xanthan gum and 0.4kg of magnesium aluminum silicate are added into an aqueous solution dispersion system, fully stirred for 15min and then transferred into a sand mill for sand milling until the particle size reaches micron level;
(4) after the reaction is finished, the 20% dinotefuran suspending agent with stable dispersion can be obtained.
Example 2
(1) Weighing 3kg of 2-mercaptoethane sodium sulfonate and 3kg of sodium allylsulfonate, dissolving into 200kg of deionized water, stirring for 15min by using a stirrer, adding 50kg of pymetrozine technical after a surfactant is completely dissolved, and placing on a high-speed dispersion machine for dispersing for 2h to prepare an aqueous solution dispersion system;
(2) adding 1.5kg of ammonium persulfate into the aqueous solution dispersion system, continuously stirring for 15min, irradiating for 24h by adopting ultraviolet irradiation equipment under the condition of starting stirring, and initiating a click reaction by ultraviolet irradiation;
(3) after the reaction is finished, 8kg of ethylene glycol, 0.5kg of defoaming agent AF1500 (chemical industry in Guangzhou province, organic silicon defoaming agent), 0.4kg of xanthan gum and 0.8kg of magnesium aluminum silicate are added into the aqueous solution dispersion system, and after the mixture is fully stirred for 15min, the mixture is transferred to a sand mill for sand milling until the particle size reaches micron level.
(4) And after the reaction is finished, obtaining the 25% pymetrozine suspending agent with stable dispersion.
Example 3
(1) Weighing 10kg of 3-mercapto-1-propane sodium sulfonate and 8kg of sodium p-styrene sulfonate, dissolving into 200kg of deionized water, stirring for 15min by using a stirrer, adding 40kg of clothianidin raw pesticide after the surfactant is completely dissolved, and placing on a high-speed dispersion machine for dispersing for 2h to prepare an aqueous solution dispersion system;
(2) adding 0.8kg of ammonium persulfate into the aqueous solution dispersion system, continuously stirring for 15min, irradiating for 24h by adopting ultraviolet irradiation equipment under the condition of starting stirring, and initiating a click reaction by ultraviolet irradiation;
(3) after the reaction is finished, adding 10kg of ethylene glycol, 0.6kg of defoaming agent AF1500 (organic silicon defoaming agent in Guangzhou's chemical industry), 0.2kg of xanthan gum and 0.6kg of magnesium aluminum silicate into the aqueous solution dispersion system, fully stirring for 15min, and then transferring the mixture into a sand mill for sand milling until the particle size reaches micron level;
(4) and after the reaction is finished, the 20% clothianidin suspending agent with stable dispersion can be obtained.
Comparative example 1: 20% dinotefuran suspending agent, adopting a traditional preparation method: the sulfonate wetting agent and the polyether nonionic surfactant are compounded, directly mixed and sanded to the micron-sized particle size, and added with other auxiliary agents to be stirred.
Comparative example 2: a25% pymetrozine suspending agent is prepared by adopting a traditional preparation method: the sulfonate wetting agent and the polyether nonionic surfactant are compounded, directly mixed and sanded to the micron-sized particle size, and added with other auxiliary agents to be stirred.
Comparative example 3: 20% clothianidin suspending agent, adopting the traditional preparation method: the sulfonate wetting agent and the polyether nonionic surfactant are compounded, directly mixed and sanded to the micron-sized particle size, and added with other auxiliary agents to be stirred.
The suspension concentrates prepared in the above examples and comparative examples were tested for centrifugal stability and thermal stability:
data processing method
1. And (3) centrifugal stability testing: each of the above examples and comparative examples was 20mL and placed in a 50mL centrifuge tube, and the centrifugal stability test was performed at 30min/8000 r. Its centrifugal stability SCCalculated by the following way:
in the formula (d)0Is the average particle size of the original sample, dCIs the average particle size of the centrifuged sample.
2. And (3) testing heat resistance stability: each of the above examples and comparative examples was 20mL each placed in a 50mL plastic bottle, and after the sealing treatment, the bottle was placed in an oven at 54 (+ -2 ℃) for 14 days. Its heat resistance stability STCalculated by the following way:
in the formula (d)0Is the average particle size of the original sample, dTIs the average particle size of the sample after 14 days in the oven.
The test results are shown in table 1:
TABLE 1 test results of examples and comparative examples
As can be seen directly from table 1, compared with the pesticide suspending agent prepared by the conventional method, the pesticide suspending agent prepared by the present invention has good appearance and dispersibility after 14 days of heat storage, and has much higher centrifugal and heat-resistant stability than the pesticide suspending agent prepared by the conventional method.
The upper and lower limit values and interval values of the process parameters (such as mass percentage, multiple, time and the like) can realize the method, and the embodiments are not listed.
In conclusion, the click chemistry reaction utilized by the invention takes water as a solvent, and the water-soluble surfactant containing sulfydryl and carbon-carbon double bonds is adopted to sand or shear the original pesticide to obtain a temporary stable pre-dispersion, and then the click chemistry reaction of the sulfydryl and the double bonds coated on the surface of the original pesticide is initiated in a form of illumination, so that the stable pesticide suspending agent is obtained; the prepared pesticide suspending agent has good dispersion effect in aqueous medium and is ultra-stable to disperse in the aqueous medium.
Claims (6)
1. A preparation method of an aqueous pesticide suspending agent is characterized by comprising the following steps: carrying out click chemical reaction on a water-soluble compound containing sulfydryl and carbon-carbon double bonds, and grafting a water-soluble functional group to the surface of a raw drug molecule in a coating mode in a light irradiation catalysis mode; the method comprises the following steps:
(1) mixing the raw pesticide and a surfactant containing sulfydryl and carbon-carbon double bonds in a proportion of 1: 0.01: 0.01-1: 1: 1, adding the solvent in an amount which is 5-20 times of the amount of the original pesticide, uniformly mixing, and dispersing the original pesticide to micron level by sanding or shearing to prepare an aqueous solution dispersion system;
the pesticide raw material is one or two of emamectin benzoate, abamectin, spinosad, indoxacarb, pymetrozine, clothianidin, dinotefuran, imidacloprid, diflubenzuron, high-efficiency cyhalothrin, methoxyfenozide, chlorantraniliprole, etoxazole and spirodiclofen;
the mercapto-containing surfactant is one or two of 2-mercaptoethane sodium sulfonate, 2, 3-mercaptopropane sodium sulfonate, 3-mercapto-1-propane sodium sulfonate and 3- (benzothiazole-2-mercapto) propane sodium sulfonate;
the surfactant containing carbon-carbon double bonds is one or two of sodium p-styrene sulfonate, sodium allyl sulfonate, sodium methyl propylene sulfonate and sodium cumene sulfonate;
the solvent is water;
(2) adding an initiator accounting for 0.1-1% of the mass of the raw pesticide into the aqueous solution dispersion system, uniformly mixing, transferring the aqueous solution dispersion system into an ultraviolet illumination box for irradiating for 24 hours, and initiating a click reaction through ultraviolet irradiation;
(3) after the reaction is finished, adding the following components in an aqueous solution dispersion system according to mass percentage: uniformly mixing 1-5% of an antifreezing agent, 0.1-0.5% of a defoaming agent, 0.1-0.5% of a viscosity regulator and 0.1-2% of a stabilizer, and then sanding or shearing until the particle size reaches the micron level;
(4) and obtaining the aqueous pesticide suspending agent after the reaction is finished.
2. The method for producing an aqueous pesticidal suspension agent according to claim 1, characterized in that: in the step (1) and the step (3), the sanding or shearing is a treatment mode of a high-speed dispersion machine, a sand mill, high-pressure micro jet and ultrasonic treatment.
3. The method for producing an aqueous pesticidal suspension agent according to claim 1, characterized in that: in the step (2), the initiator is inorganic peroxide and is one or two of ammonium persulfate, sodium persulfate and potassium persulfate.
4. The method for producing an aqueous pesticidal suspension agent according to claim 1, characterized in that: in the step (3), the antifreezing agent is one of ethanol, isooctanol and urea; the defoaming agent is an organic silicon defoaming agent; the viscosity regulator is one or two of xanthan gum, organic bentonite and polyethylene glycol; the stabilizer is magnesium aluminum silicate.
5. The method for producing an aqueous pesticidal suspension agent according to claim 1, characterized in that: the solvent used in the step (1) is deionized water.
6. An aqueous pesticidal suspension prepared by the preparation method according to any one of claims 1 to 5, characterized in that: the aqueous pesticide suspending agent overcomes the defect that the original pesticide cannot resist high temperature, and has good dispersion effect in an aqueous medium.
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