CN114766476B - Method for prolonging duration of profenofos aqueous solution - Google Patents
Method for prolonging duration of profenofos aqueous solution Download PDFInfo
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- CN114766476B CN114766476B CN202210407897.4A CN202210407897A CN114766476B CN 114766476 B CN114766476 B CN 114766476B CN 202210407897 A CN202210407897 A CN 202210407897A CN 114766476 B CN114766476 B CN 114766476B
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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
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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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/14—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing aromatic radicals
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Abstract
The invention provides a method for prolonging the duration of profenofos aqueous solution, which fully inspects the photodegradation phenomenon of profenofos aqueous solution under the conditions of sunlight and artificial light source, utilizes cornflower-3-O-glucoside to prolong the duration of profenofos, mixes the cornflower-3-O-glucoside with the profenofos aqueous solution, has the concentration of profenofos of 5 mu mol/L, the content of the cornflower-3-O-glucoside of 2.42-48.48 mg/L, has the photolytic half-life of profenofos of 98.88-247.55 h under the sunlight, prolongs the 1.09-2.75 times than that of a control group (profenofos aqueous solution without the cornflower-3-O-glucoside), does not change the main metabolic path of profenofos, and has wide agricultural application prospect.
Description
Technical Field
The invention belongs to the technical field of plant protection, and particularly relates to a method for prolonging the duration of profenofos aqueous solution.
Background
Profenofos (profenofos) is a moderately toxic systemic broad-spectrum organophosphorus insecticide, also known as bromclophos, duotoxin, widely used in the united states, china, thailand, vietnam, pakistan, australia, japan, egypt, brazil, australia and india, for controlling insect pests on cotton, coconut, green pepper, fruit, currant, tomato, shallot, okra, curry leaf, peppermint leaf, coriander leaf, and rice and vegetables. Profenofos can phosphorylate the active site of detoxification enzyme-acetylcholinesterase in insects, and phosphorylase can not function to cause accumulation of acetylcholinergic at synaptic junction, thereby causing neuronal disorder, hyperexcitability, spasm, paralysis and death of pests. The profenofos not only has high efficiency and low toxicity, but also has high insecticidal activity on pests of drug resistant crops. Because the pesticide does not generate cross resistance with most organophosphorus, carbamate and pyrethroid pesticides in the market, and the mixed application has a synergistic effect, the development prospect of profenofos is wider under the condition of phase out of high-toxicity pesticide varieties.
Cyanidin-3-O-glucoside (Cyanidin-3-glucoside) is mainly present in plants such as blood orange, rice, purple potato and blueberry, and is the most stable and easily available anthocyanin in nature. The plant anti-oxidation agent is used for the anti-oxidation defense of plants, plays an important role in growth regulation, hormone activity, antibacterial activity, pH regulation, metabolism and dormancy induction, and can protect cotton leaves from being damaged by cotton bollworms. In addition, the cyanidin-3-O-glucoside can be used as an ultraviolet absorbent to reduce direct injury caused by ultraviolet irradiation, and has various medical care effects of resisting oxidation, inflammation, cancer, protecting nerves, recovering transient vision weakness and the like. The dosage is below 500mg/L, and the cyanidin-3-O-glucoside is harmless to human body and environment.
After the profenofos is sprayed on the surface of crops, the efficacy of the profenofos is gradually weakened after photolysis and hydrolysis, and how to avoid photochemical degradation of the profenofos aqueous solution so as to prolong the pesticide duration becomes a research hot spot.
Disclosure of Invention
The invention aims to provide a method for prolonging the duration of a profenofos aqueous solution.
In order to achieve the aim of the invention, the invention provides a composition which is prepared by mixing profenofos and cyanidin-3-O-glucoside according to the mol ratio of 1:1-1:20.
Preferably, the molar ratio of profenofos to procyanidin-3-O-glucoside is 1:1, 1:5, 1:10 or 1:20.
In a second aspect, the invention provides the use of the composition in the preparation of a pesticide.
In a third aspect, the present invention provides an insecticide which is an aqueous profenofos solution containing cyanidin-3-O-glucoside, wherein the composition is formulated by dissolving the composition in an appropriate amount of an organic solvent and then using water as a solvent.
The content of procyanidin-3-O-glucoside in the profenofos aqueous solution is less than or equal to 500mg/L.
Preferably, the content of procyanidin-3-O-glucoside in the 5. Mu. Mol/L profenofos aqueous solution is less than or equal to 48.48mg/L, more preferably 2.42-48.48 mg/L.
The corresponding procyanidin-3-O-glucoside can be increased according to the concentration of profenofos applied, and the maximum is not more than 500mg/L.
Preferably, the organic solvent may be selected from methanol, acetonitrile, acetone, and the like.
In a third aspect, the invention provides the use of procyanidin-3-O-glucoside in extending the photolytic half-life of an aqueous profenofos solution.
In a fourth aspect, the invention provides a method for prolonging the duration of a profenofos aqueous solution, wherein procyanidine-3-O-glucoside is added into the profenofos aqueous solution to ensure that the final concentration is less than or equal to 500mg/L.
Preferably, the molar ratio of profenofos to procyanidin-3-O-glucoside is from 1:1 to 1:20, more preferably 1:1, 1:5, 1:10 or 1:20.
Preferably, the final concentration of procyanidin-3-O-glucoside is less than or equal to 48.48mg/L, more preferably 2.42-48.48 mg/L, to 5. Mu. Mol/L profenofos aqueous solution.
By means of the technical scheme, the invention has at least the following advantages and beneficial effects:
the invention provides a method for prolonging the duration of profenofos by utilizing cornflower-3-O-glucoside through fully examining the photodegradation phenomenon of profenofos aqueous solution under the conditions of sunlight and artificial light source, which is characterized in that the cornflower-3-O-glucoside is mixed with profenofos aqueous solution, the content of the cornflower-3-O-glucoside is 2.42-48.48 mg/L, the photolytic half life of profenofos is 98.88-247.55 h under sunlight, and the method prolongs the main metabolism path of profenofos by 1.09-2.75 times compared with a control group (profenofos aqueous solution without the cornflower-3-O-glucoside), and has wide agricultural application prospect.
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FIG. 1 shows the degradation of DMPO-OH, DMPO-RO. Spectra (a) and TEMPO-by propylbromide phosphorescence in a preferred embodiment of the present invention 1 O 2 A spectrum (b), a profenofos cyanidin-3-O-glucoside photodegradation spectrum (c) and a profenofos cyanidin-3-O-glucoside photodegradation spectrum (d).
FIG. 2 is a graph showing the relationship between the light irradiation time and the residual concentration of profenofos at different molar ratios of profenofos (5. Mu. Mol/L) to procyanidin-3-O-glucoside in a high-pressure mercury lamp according to the preferred embodiment of the present invention.
FIG. 3 is a graph showing the relationship between the light irradiation time and the residual concentration of profenofos in different molar ratios of profenofos (5. Mu. Mol/L) to procyanidin-3-O-glucoside under sunlight in the preferred embodiment of the invention.
FIG. 4 is a graph showing the relationship between the light irradiation time and the residual concentration of profenofos (5. Mu. Mol/L) and five flavonoid compounds in a molar ratio of 1:5 under a high-pressure mercury lamp in the preferred embodiment of the present invention.
Detailed Description
In order to safely and efficiently utilize profenofos, the invention provides a method for prolonging the duration of profenofos by utilizing the procyanidine-3-O-glucoside which is most stable in nature and is easy to obtain: the cornflower-3-O-glucoside is mixed with the profenofos aqueous solution, the input amount of the cornflower-3-O-glucoside is 2.42-48.48 mg/L, the photolytic half life of profenofos is 98.88-247.55 h under sunlight, the primary metabolic path of profenofos is prolonged by 1.09-2.75 times, and the profenofos is not changed.
1. The procyanidin-3-O-glucoside can effectively prolong the half-life of the profenofos aqueous solution under the irradiation of four different light sources
The molar ratio of profenofos (5 mu mol/L) to procyanidin-3-O-glucoside is 1:0-1:20, the photodegradation half-life of profenofos under 4 light sources of high-pressure mercury lamp, ultraviolet lamp, xenon lamp and sunlight is 8.09-37.41 min, 6.12-11.28 h, 8.24-15.74 h and 89.90-247.55 h respectively, the procyanidin-3-O-glucoside has obvious inhibition effect on photodegradation of profenofos, and the photodegradation of profenofos is reduced by 1.18-4.6 times, 1.19-1.84 times, 1.12-1.91 times and 1.10-2.75 times respectively under the irradiation of the high-pressure mercury lamp, the ultraviolet lamp, the xenon lamp and the sunlight when the molar ratio of profenofos to procyanidin-3-O-glucoside is 1:1-1:20 along with the increase of the procyanidin-3-O-glucoside. Under the condition of high-pressure mercury lamp, the light quenching effect of the cyanidin-3-O-glucoside is larger than that of sunlight, ultraviolet lamp and xenon lamp irradiation.
2. Light-inhibition degradation mechanism of procyanidin-3-O-glucoside on profenofos aqueous solution
In order to explore the types of active oxidized species involved in the photodegradation reaction of profenofos in ultrapure water and in aqueous solutions of procyanidin-3-O-glucoside, detection was carried out using electron spin paramagnetic capture (ESR). The 5, 5-dimethyl-1-pyrroline nitrogen oxide (DMPO) is a capturing agent of hydroxyl free radicals, a profenofos aqueous solution DMPO system does not generate signals under a dark condition, and after 1min of illumination, characteristic peaks of 1:2:2:1 appear in the system, which indicate that the profenofos aqueous solution system has OH when the illumination is carried out for 1min, and after 2min of illumination, signals of DMPO-alkoxy free radicals are superposed on the basis of DMPO-OH signals. The aqueous solution of the cornflower-3-O-glucoside and the aqueous solution of the profenofos-cornflower-3-O-glucoside have no signal in darkness and illumination for 2min, which indicates that no OH exists in the aqueous solution system of the cornflower-3-O-glucoside, and the cornflower-3-O-glucoside can remove OH and RO which are generated under the illumination condition of the aqueous solution of the profenofos, thereby inhibiting the photodegradation of the profenofos. 4-hydroxy-2, 6-tetramethyl piperidinyloxy (TEMP) is a capturing agent of singlet oxygen, a photosensitizer in the solution forms a triplet state through light excitation transition, singlet oxygen (excited oxygen molecules) can be generated by combining molecular oxygen, stable nitroxide free radical TEMPO is formed after the TEMP captures the singlet oxygen, and the generation rate and concentration change of the singlet oxygen can be obtained through ESR signal analysis of the TEMPO and combination of reaction progress. Under dark condition, the TEMP system of the profenofos aqueous solution only has the background signal of TEMPO, and after 1min of illumination, the system has characteristic peaks of 1:1:1, which indicates that the profenofos aqueous solution system has the following characteristics 1 O 2 Exists. The water solution of cyanidin-3-O-glucoside and the water solution of profenofos added with cyanidin-3-O-glucoside have no TEMPO-like effect in the dark and 1min of illumination 1 O 2 Characteristic peaks, indicating the absence of procyanidin-3-O-glucoside in aqueous systems 1 O 2 。
ESR spectrum shows that profenofos can generate hydroxyl free radical, alkoxy free radical and singlet oxygen, and the free radicals are not detected in the reaction system after the procyanidin-3-O-glucoside is added, and the photoinhibition degradation effect of the procyanidin-3-O-glucoside on profenofos aqueous solution is caused by the fact that the free radicals generated by profenofos self-sensitization reaction are removed by the procyanidin-3-O-glucoside.
The spectrum of the DMPO-OH and DMPO-RO by the phosphorescence degradation of the propyl bromide is shown in figure 1 (a), and the TEMPO-RO by the phosphorescence degradation of the propyl bromide 1 O 2 The spectrum is shown in figure 1 (b), the profenofos cornflower-3-O-glucoside photodegradation spectrum is shown in figure 1 (c), and the profenofos cornflower-3-O-glucoside photodegradation spectrum is shown in figure 1 (d).
FIG. 2 shows a spectrum (a) of DMPO-OH, DMPO-RO by phosphorescence degradation of propyl bromide and TEMPO-OH by phosphorescence degradation of propyl bromide 1 O 2 EPR spectrum (b), profenofos cornflower-3-O-glucoside photodegradation EPR spectrum (c), profenofos cornflower-3-O-glucoside photodegradation EPR spectrum (d).
3. Effect of cyanidin-3-O-glucoside on propyl bromide phosphorescence degradation products
The profenofos self photodegradation product is O- (2-chlorophenyl) -O-ethyl-S-propyl-phosphorothioate, the original photodegradation path of profenofos is not changed after the cyanidin-3-O-glucoside is added, and the photodegradation of the product can be inhibited to cause the continuous accumulation of the content of the product in a reaction system.
The following examples are illustrative of the invention and are not intended to limit the scope of the invention. Unless otherwise indicated, the technical means used in the examples are conventional means well known to those skilled in the art, and all raw materials used are commercially available.
EXAMPLE 1 light-inhibited degradation of profenofos by procyanidin-3-O-glucoside in pure Water under high pressure mercury Lamp
Preparing a profenofos standard substance into a standard solution with the concentration of 500mg/L by using methanol, preparing a procyanidin-3-O-glucoside into a standard solution with the concentration of 1000mg/L by using methanol, transferring a proper amount of profenofos standard solution and a procyanidin-3-O-glucoside standard solution into a volumetric flask with a plug, diluting a reaction system into a mixed solution with the molar ratio of profenofos to procyanidin-3-O-glucoside of 1:0, 1:1, 1:5, 1:10 and 1:20 respectively by using pure water, wherein the concentration of profenofos is 5 mu mol/L, and uniformly mixing the mixed solution by ultrasonic treatment for 3 min. 10mL of the mixed reaction solution is taken out and placed in a quartz tube, and a high-pressure mercury lamp is placed, meanwhile, a dark control group is tightly wrapped by tinfoil paper, and 3 groups of test groups and control groups are parallel. The high-pressure mercury lamp is purchased from Wo Laibo instrument and equipment limited company, the illumination intensity is 105000 ～ 1200001x, the power is 500w, the temperature is 30 ℃, figure 2 is a graph of the effect of procyanidin-3-O-glucoside on inhibiting the phosphorescence degradation of profenofos under the high-pressure mercury lamp condition, the samples are taken and detected at the time points of illumination of 0min, 5min, 10min, 15min, 20min, 25min and 30min respectively, and the photodissociation half-life of profenofos is 8.09min, 9.54min, 14.76min, 21.74min and 37.41min respectively under the conditions that the molar ratio of profenofos to procyanidin-3-O-glucoside is 1:0, 1:1, 1:5, 1:10 and 1:20 respectively, and the photodissociation rate of profenofos in a dark control group is reduced by 1.18-4.6 times.
EXAMPLE 2 photo-inhibited degradation of profenofos by procyanidin-3-O-glucoside in pure Water under sunlight
Preparing a profenofos standard substance into a standard solution with the concentration of 500mg/L by using methanol, preparing a procyanidin-3-O-glucoside into a standard solution with the concentration of 1000mg/L by using methanol, transferring a proper amount of profenofos standard solution and a procyanidin-3-O-glucoside standard solution into a volumetric flask with a plug, diluting a reaction system into a mixed solution with the molar ratio of profenofos to procyanidin-3-O-glucoside of 1:0, 1:1, 1:5, 1:10 and 1:20 respectively by using pure water, wherein the concentration of profenofos is 5 mu mol/L, and uniformly mixing the mixed solution by ultrasonic treatment for 3 min. 10mL of the mixed reaction solution is taken out and placed in a quartz tube and placed under sunlight, meanwhile, a dark control group is tightly arranged by wrapping with tinfoil paper, and 3 groups of experimental groups and control groups are parallel. The experimental place is combined with the mountain area (N31 DEG 52', E117 DEG 17'), the date is 7-10 months 9:00-17:00, the sunlight intensity is 36000-110000lx, and the temperature is 35-47 ℃. FIG. 3 is a graph showing the effect of procyanidin-3-O-glucoside on inhibiting the phosphorescence degradation of profenofos under the sunlight condition, wherein the samples are respectively taken and detected at the time points of illumination of 0h, 4h, 8h, 12h, 16h, 20h and 24h, and the degradation half-life of profenofos is 89.90h, 98.88h, 108.64h, 180.04h and 247.55h respectively under the condition that the molar ratio of profenofos to procyanidin-3-O-glucoside is 1:0, 1:1, 1:5, 1:10 and 1:20, and the degradation amount of profenofos in a dark control group is extremely small.
Example 3 comparison of the light-inhibiting degradation effects of different flavonoid compounds on profenofos in pure water under a high pressure mercury lamp
The standard substance of profenofos is prepared into standard solution with the concentration of 500mg/L by using methanol, five flavonoid compounds of catechin, epicatechin, gallic acid, procyanidine and cyanidin-3-O-glucoside are respectively prepared into standard solution with the concentration of 1000mg/L by using methanol, the standard solution with the concentration of 1000mg/L is prepared into standard solution with the concentration of 1000mg/L by using methanol, the reaction system is diluted into mixed solution with the molar ratio of profenofos and flavonoid compounds of 1:0 and 1:5 respectively by using pure water, wherein the concentration of profenofos is 5 mu mol/L, and the mixed solution is evenly mixed by ultrasonic treatment for 3 min. 10mL of the mixed reaction solution is taken out and placed in a quartz tube, and a high-pressure mercury lamp is placed, meanwhile, a dark control group is tightly wrapped by tinfoil paper, and 3 groups of test groups and control groups are parallel. The time points of illumination for 0min, 5min, 10min, 15min, 20min, 25min and 30min are respectively sampled and detected, the relation between the illumination time of profenofos (5 mu mol/L) and five flavonoid compounds and the residual concentration of profenofos under a high-pressure mercury lamp is shown as figure 4, the inhibition effect of procyanidin-3-O-glucoside in the flavonoid compounds on the phosphorescent degradation of profenofos is strongest, and the procyanidin-3-O-glucoside is the most stable and easily obtained flavonoid compound in nature and widely exists in various parts of vegetables, fruits and other plants, such as flowers, leaves, stems, buds and grains, and the antioxidant capacity of the procyanidin-3-O-glucoside is obviously stronger than that of other flavonoid compounds.
While the invention has been described in detail in the foregoing general description and with reference to specific embodiments thereof, it will be apparent to one skilled in the art that modifications and improvements can be made thereto. Accordingly, such modifications or improvements may be made without departing from the spirit of the invention and are intended to be within the scope of the invention as claimed.
Claims (2)
1. An insecticide, which is a cornflower-3-containing insecticideOAn aqueous profenofos solution of a glucoside, which is prepared from profenofos and procyanidin-3-O-glucoside in a ratio of 1:5 or 1:the composition is prepared by dissolving a composition mixed by a molar ratio of 10 or 1:20 with an organic solvent, and then taking water as a solvent, wherein the organic solvent is selected from methanol, acetonitrile and acetone, and the concentration of profenofos is 5 mu mol/L.
2. A method for prolonging the duration of a profenofos aqueous solution is characterized in that procyanidin-3-OGlucoside, 5. Mu. Mol/L aqueous profenofos and procyanidin-3-OThe molar ratio of the glucosides is 1:5 or 1:10 or 1:20.
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| EP0024731A1 (en) * | 1979-08-30 | 1981-03-11 | The Coca-Cola Company | A photostable anthocyanic colorant composition and its use in a food composition |
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| GB1592691A (en) * | 1976-10-05 | 1981-07-08 | Ici Australia Ltd | Stabilised tickicidal compositions |
| US20120164089A1 (en) * | 2007-06-21 | 2012-06-28 | Suntava, Llc | Anthocyanin pigment/dye compositions and solutions through corn extraction |
| WO2014101237A1 (en) * | 2012-12-31 | 2014-07-03 | 深圳诺普信农化股份有限公司 | Photolysis-resistant pesticide and applications thereof |
| CN105030560B (en) * | 2015-07-13 | 2018-10-12 | 暨南大学 | Cy-3-G induces UVB the protective action of HaCaT cellular damages |
| CN107950551A (en) * | 2017-12-25 | 2018-04-24 | 云南保山嘉宏农业开发（集团）有限公司 | Pure biology neem-based insecticide preparation process |
| CN108651488A (en) * | 2018-05-28 | 2018-10-16 | 徐建自 | A kind of abamectin emulsifiable concentrate preparation |
| CN113648321B (en) * | 2021-07-23 | 2023-03-24 | 南京师范大学 | cyanidin-3-O-glucoside and application of addition product of cyanidin-3-O-glucoside and acrolein as acrolein inhibitor |
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| EP0024731A1 (en) * | 1979-08-30 | 1981-03-11 | The Coca-Cola Company | A photostable anthocyanic colorant composition and its use in a food composition |
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| 黑莓汁花色苷热降解动力学及降解机理;张丽霞;周剑忠;顾振新;黄开红;刘小莉;陆卿卿;;江苏农业学报(05);第1111-1116页 * |
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