CN111345305A - Topramezone-containing herbicide and preparation method thereof - Google Patents

Topramezone-containing herbicide and preparation method thereof Download PDF

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Publication number
CN111345305A
CN111345305A CN202010313777.9A CN202010313777A CN111345305A CN 111345305 A CN111345305 A CN 111345305A CN 202010313777 A CN202010313777 A CN 202010313777A CN 111345305 A CN111345305 A CN 111345305A
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topramezone
herbicide
terbuthylazine
methyl
salt
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王铭
赵守明
张彩
苏跃
郭家志
绳继增
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Shandong Dehao Chemical Co ltd
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Shandong Dehao Chemical Co ltd
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    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N39/00Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
    • A01N39/02Aryloxy-carboxylic acids; Derivatives thereof
    • A01N39/04Aryloxy-acetic acids; Derivatives thereof
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/661,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
    • A01N43/681,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms directly attached to ring carbon atoms
    • A01N43/70Diamino—1,3,5—triazines with only one oxygen, sulfur or halogen atom or only one cyano, thiocyano (—SCN), cyanato (—OCN) or azido (—N3) group directly attached to a ring carbon atom

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

Abstract

The invention discloses a herbicide containing topramezone, which comprises the following effective components: topramezone, terbuthylazine, and 2-methyl-4-chlorodimethylamine salt; the weight ratio of the topramezone to the terbuthylazine to the 2-methyl-4-chlorodimethylamine salt is 1-10:10-20: 30-40. The herbicide provided by the invention is prepared by compounding different active ingredients, and the herbicide adopting the topramezone can avoid the problem of resistance caused by long-term single use and can prolong the service life of the herbicide.

Description

Topramezone-containing herbicide and preparation method thereof
Technical Field
The invention relates to the technical field of herbicides, and in particular relates to a herbicide containing topramezone and a preparation method thereof.
Background
Topramezone, the name of which is 4- [3- (4, 5-dihydroisoxazol-3-yl) -2-methyl-4-methylsulfonyl ] -1-methyl-5-hydroxy-1H-pyrazole, is the first benzyl pyrazolone herbicide developed by basf, and also belongs to a p-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitor, which has a good control effect on weeds resistant to glyphosate, triazines, acetolactate synthase (ALS) inhibitors and acetyl coenzyme A carboxylase (ACCase) inhibitors, can control main gramineous weeds and broadleaf weeds on corn crops worldwide, but is high in cost when used alone, so that the topramezone is not suitable for large-area popularization and use.
2 methyl 4 chloro dimethylamine salt is inhaled by weeds stem leaf, inhibits the synthesis of nucleic acid metabolism and protein at the weeds top, makes the growing point stop growing, and young leaf can not extend, and the photosynthesis can not normally go on, conducts the medicament of plant lower part, makes the synthesis of plant stem tissue's nucleic acid and protein increase, promotes cell abnormal division, and the root tip expands, loses the absorptive capacity, causes the stem stalk distortion, deformity, the screen pipe blocks up, phloem destruction, and organic matter transportation is obstructed to destroy the normal viability of plant.
Triazine herbicides are one of the traditional herbicides that were introduced as early as the 50 s of the 20 th century. It acts by inhibiting photosynthesis of plants through photosynthesis system II (PS II) with D1 protein as the target. The triazine product is used as a large class of herbicide, the main varieties comprise atrazine, ametryn, terbuthylazine, terbutryn, simazine, simetryn, prometryn and the like, the herbicide plays a great role in agriculture, but due to large using amount and long residue, the atrazine is suitable for preventing and killing crabgrass, barnyard grass, green bristlegrass, sedge, alopecurus, polygonum, chenopodium album, cruciferae and leguminous weeds in dry field crops such as corns, broomcorn, sugarcanes, fruit trees, nurseries, forests and the like, particularly has good selectivity on corns, and also has a certain inhibition effect on certain perennial weeds.
According to the invention, the topramezone, the 2-methyl-4-chlorodimethylamine salt and the terbuthylazine are compounded, and the synergistic effect is found in the compounding process.
Disclosure of Invention
The invention discloses a topramezone-containing herbicide and a preparation method thereof, and the herbicide comprises the following effective components: topramezone, terbuthylazine and 2-methyl-4-chlorodimethylamine salt.
The weight ratio of the topramezone to the terbuthylazine to the 2-methyl-4-chlorodimethylamine salt is 1-10:10-20: 30-40;
preferably, the weight ratio of topramezone to terbuthylazine to 2-methyl-4-chlorodimethylamine salt is 1:20: 30.
The weight percentage of the effective component in the topramezone-containing herbicide is 5-60%.
The formulation of the pyraflufen-ethyl herbicide can be any formulation known in the field, such as wettable powder, dispersible oil suspending agent, missible oil, water dispersible granules, water suspending agent and the like.
The herbicide contains various agriculturally acceptable auxiliary agents required for preparing a pesticide preparation, and comprises one or more of a solvent, an emulsifier, a wetting agent, a stabilizer, a dispersing agent, a penetrating agent, a thickening agent, an antifoaming agent, an antifreezing agent, a disintegrating agent, a binder, a filler, a carrier, a medium and a surfactant, which are known substances, can be changed according to different situations, and are not particularly limited.
Taking wettable powder as an example, the method can be implemented by adding a dispersing agent, a wetting agent and a filler into the active ingredients.
Wherein the dispersant is one or the combination of any more of alkyl naphthalene formaldehyde condensate sulfonate, 2-naphthalene sulfonic acid formaldehyde condensate sodium salt, polycarboxylate, methylene bis (methyl) naphthalene sulfonate, polyether and commonly used dispersant in the field.
The wetting agent is one or the combination of any one of alkyl naphthalene sulfonate, sodium dodecyl sulfate, sodium lignosulfonate, fatty alcohol-polyoxyethylene ether, alkylphenol polyoxyethylene polyoxypropylene ether, fatty alcohol-polyoxyethylene polyoxypropylene ether sulfate, alkylphenol polyoxyethylene polyoxypropylene ether sulfate and wetting agents commonly used in the field.
The filler is one or the combination of more of kaolin, bentonite, diatomite, white carbon black, light calcium carbonate and attapulgite.
The preparation method of the wettable powder comprises the steps of putting topramezone, terbuthylazine, 2-methyl-4-chlorodimethylamine salt dispersant, wetting agent and filler into a mixing kettle, uniformly stirring, then passing the uniformly mixed material through an airflow pulverizer, then passing the uniformly mixed material through the mixing kettle again, uniformly stirring, sieving with a 325-mesh sieve in fineness, and subpackaging after all indexes are qualified, thus obtaining the wettable powder.
The invention has the beneficial effects that:
(1) the herbicide provided by the invention is compounded by three active ingredients, can avoid the problem of resistance generation caused by long-term single use, and can prolong the service life of the herbicide.
(2) Compared with a single herbicide, the herbicide provided by the invention expands the weed control spectrum and the application range, can be used in corn crop fields, and has good weeding effects on weeds such as crabgrass, barnyard grass, bindweed, sowthistle herb, and abnormal sedge.
(3) The herbicide provided by the invention has the advantages that the dosage of each single dose is greatly reduced within a specific proportion range, the medication cost is saved, and the labor intensity is reduced. The herbicide has long lasting period, still has good control effect within 60 days, and can realize the desire of once controlling most weeds in one growing season.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. The experimental methods in the following examples, which are not specified under specific conditions, were generally conducted under conventional conditions. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs.
EXAMPLE 1 an aqueous dispersion of topramezone-containing formulation
The active ingredients of the herbicide are topramezone, terbuthylazine and 2-methyl-4-chlorodimethylamine salt, the weight ratio of the topramezone to the terbuthylazine to the 2-methyl-4-chlorodimethylamine salt is 1:10:30, and the weight percentage of the active ingredients in the herbicide is 40%.
The preparation method comprises the following steps: 9.8 g of topramezone, 97.6 g of terbuthylazine, 292.6 g of 2-methyl-4-chlorodimethylamine salt, 150 g of naphthalenesulfonate formaldehyde condensate, 130 g of calcium lignosulfonate, 60 g of K12, 60 g of sodium sulfate, 60 g of polyethylene glycol and 140 g of kaolin are put into a mixer in sequence, the materials are stirred for 30 minutes to be uniformly mixed, then the materials pass through a gas flow pulverizer, and the material fineness passes through a 325-mesh sieve. Adding 100 ml of water, uniformly mixing to obtain a wet material, manufacturing 20-mesh granules by a wet method, drying in a tray in a hot air oven at 45 ℃ for 2 hours, and after drying, sieving by a 18-mesh sieve, and finishing granules to obtain the water dispersible granules.
Example 2 dispersible oil suspension containing topramezone
The active ingredients of the topramezone-terbuthylazine wettable powder are topramezone, terbuthylazine and 2-methyl-4-chlorodimethylamine salt, the weight ratio of the topramezone to the terbuthylazine to the 2-methyl-4-chlorodimethylamine salt is 10:20:40, and the weight percentage of the active ingredients in the topramezone-terbuthylazine wettable powder is 60%.
The preparation method comprises the following steps: 250 g of soybean oil, 40 g of nonylphenol polyoxyethylene ether, 30 g of castor oil polyoxyethylene ether and 40 g of calcium dodecylbenzenesulfonate are added into a container, and then 85.7 g of topramezone, 171.4 g of terbuthylazine, 342.9 g of 2-methyl-4-chlorodimethylamine salt and 40 g of white carbon black are added while stirring. Then stirred for 30 minutes to mix the materials evenly. And opening circulating water to control the sand mill to be below 40 ℃, and sanding the material to obtain the dispersible oil suspending agent with the fineness D90 of less than or equal to 5 micrometers.
Example 3 Topramezone wettable powder
The active ingredients of the topramezone-terbuthylazine wettable powder are topramezone, terbuthylazine and 2-methyl-4-chlorodimethylamine salt, the weight ratio of the topramezone to the terbuthylazine to the 2-methyl-4-chlorodimethylamine salt is 1:20:30, and the weight percentage of the active ingredients in the topramezone-terbuthylazine wettable powder is 5%.
The preparation method comprises the following steps: 0.98g of topramezone, 19.61g of terbuthylazine, 29.41g of 2-methyl-4-chlorodimethylamine salt, 430 g of white carbon black, 430 g of methylene bis-methyl naphthalene sodium sulfonate and 90 g of sodium dodecyl sulfate are sequentially put into a mixer, stirred for 30 minutes to uniformly mix the materials, then the materials pass through an airflow pulverizer, the fineness D90 of the materials is less than or equal to 15 micrometers, and then the materials are mixed and stirred in the mixer again to obtain the wettable powder.
Experimental example 1 evaluation of Effect of mixing
The invention uses the components of topramezone, terbuthylazine, 2-methyl-4-chlorodimethylamine salt and the like to carry out indoor toxicity determination research, and the specific method comprises the following steps: the stem and leaf treatment is carried out by an indoor pot culture method, and the test refers to' indoor pesticide bioassay test criteria herbicide part 4
1. The tested weeds:
herba Ixeritis Denticulatae, and herba Cyperi.
2. And (3) experimental design:
topramezone was set at 1, 4, 7, 10ug/ml4 dose treatments, terbuthylazine: 10. 4 doses of 20, 40 and 80ug/ml, 4 doses of 2-methyl-4-chlorodimethylamine salt of 10, 20, 30 and 40ug/ml, and 8 doses of 1+10+30, 1+10+40, 1+20+30, 1+20+40, 10+10+30, 10+10+40, 10+20+30 and 10+20+40ug/ml for mixed treatment of topramezone, terbuthylazine and 2-methyl-4-chlorodimethylamine salt, and 1 clear water control for four times.
3. Test method
The preparation method comprises the steps of preparing 5% of a preparation from topramezone, terbuthylazine and 2-methyl-4-chlorodimethylamine salt, using a potting culture method for culturing target weeds, carrying out air drying and sieving on soil collected from a corn field without using a herbicide, then carrying out potting, and quantifying 4/5 parts of dry soil in the pot to completely moisten the soil, wherein the pH value of the soil is 7.0, the content of organic matters is 1.1%, uniformly dibbling about 70 seeds of sowthistle and abnormal sedge collected in the field on the surface of the soil after soaking, covering 0.8-1.0cm of soil, placing the seeds in a greenhouse for conventional culture, keeping the soil moist in the culture process, setting 60 weeds in each pot after the weeds appear for a second, spraying the weeds in a spraying tower at the 3-5 leaf stage (the spraying pressure is 2.75MPa, and the spraying liquid amount is 25 Kg/mu), continuously placing the seedlings in the greenhouse for culture and observing after the application, and repeating for four times.
4. Investigation and analysis method
And (3) observing the growth state, the poisoning symptom and the phytotoxicity degree of the weeds by visual observation at regular intervals after application, shearing and treating the overground part 15d after application, weighing by adopting an electronic balance, and calculating the fresh weight control effect:
e (%) ═ X100 (fresh weight of weeds in treatment area/fresh weight of weeds in control area)
The Colby method is used to evaluate the action type of the mixed medicament.
Figure BDA0002458689000000051
In the formula: a: the actual weed fresh weight of herbicide 1 is a percentage of the control fresh weight;
b: the actual fresh weight of herbicide 2 was a percentage of the control fresh weight;
c: the actual fresh weight of herbicide 3 was a percentage of the control fresh weight;
n: the number of varieties of the compound herbicide;
E0the percentage theoretical value of the fresh weight of the reference is calculated when the medicaments are mixed;
e is the actual percentage of the control fresh weight when the medicaments are mixed.
E0﹣E>10% of the composition is synergistic effect; e0﹣E<Antagonism is found at 10%; an addition between-10 and 10.
5. Results and analysis
TABLE 1 Effect of topramezone, terbuthylazine and 2-methyl-4-chloro dimethylamine salt on Ixeris denticulata
Figure BDA0002458689000000052
Figure BDA0002458689000000061
As can be seen from table 1, when the ratio of the three is: 1-10:10-20:30-40, EOThe value of E is more than 10 percent, which indicates that the combination of the components in the proportion has synergistic effect on the control effect of the Ixeris denticulata.
TABLE 2 Effect of topramezone, terbuthylazine and 2-methyl-4-chlorodimethylamine salt on the control of sedges
Figure BDA0002458689000000062
Figure BDA0002458689000000071
As can be seen from table 2, when the ratio of the three is: 1-10:10-20:30-40, EOThe value of E is more than 10 percent, which indicates that the compound has synergistic effect on the control effect of the special-shaped cyperus rotundus.
Experimental example 2 field experiment
The specific test operations were as follows:
the herbicides obtained in examples 1 to 3;
control agent 1: topramezone wettable powder;
control agent 2: terbuthylazine wettable powder;
control pharmacology 3: 2-methyl-4-chlorodimethylamine salt wettable powder.
Test subjects: investigating the control effect of the medicament on various weeds and the control effect of the total weeds. The main weeds in the field are large crabgrass, barnyard grass, field bindweed, ixeris sonchifolia, abnormal sedge and the like.
The application method and the field management are as follows: spraying, spreading or mixing soil according to the local farming method.
Cell design: the cells were randomly arranged in groups of 30 square meters per cell, with 4 repetitions.
And (4) control effect investigation: and 4 points are randomly selected in each cell by an absolute value method, each point is sampled by 0.25 square meter, the number of weed plants is counted, and the plant control effect is determined.
Figure BDA0002458689000000072
TABLE 3 control of the plants 30 days after drug administration
Figure BDA0002458689000000073
Figure BDA0002458689000000081
As can be seen from the above table, the total weed control effect of the herbicides prepared in examples 1-3 can reach more than 93%, which is higher than that of the control agent.
And (5) sampling again 60 days after the herbicide is applied, counting the growth and growth of weeds in different agent treatment plots, calculating the fresh weight control effect of each treated weed, and evaluating the lasting period of the agent.
Figure BDA0002458689000000082
TABLE 4 fresh weight control effect 60 days after drug administration
Figure BDA0002458689000000083
As can be seen from the above table, the total fresh grass weight control effect of the herbicides prepared in examples 1-3 was over 85% higher than that of the control agents 1, 2 and 3.
Tests show that the compound has good selectivity and no obvious phytotoxicity symptoms when applied to a corn field, the growth vigor of the compound after being applied for 60 days is equivalent to that of blank control agents and control agents, the compound can normally branch/divide leaves for reproductive growth, and the plant height and the leaf age are not inhibited visually.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein. In addition, the technical solutions between the various embodiments can be combined with each other, but must be based on the realization of those skilled in the art; where combinations of features are mutually inconsistent or impractical, such combinations should not be considered as being absent and not within the scope of the claimed invention.

Claims (9)

1. A topramezone-containing herbicide, which is characterized in that: the effective components of the composition comprise: topramezone, terbuthylazine, and 2-methyl-4-chlorodimethylamine salt; the weight ratio of the topramezone to the terbuthylazine to the 2-methyl-4-chlorodimethylamine salt to the terbuthylazine is 1-10:10-20: 30-40.
2. The topramezone-containing herbicide of claim 1, wherein: the weight percentage of the effective component in the topramezone-containing herbicide is 5-60%.
3. The topramezone-containing herbicide of claim 1, wherein: the weight ratio of the topramezone to the terbuthylazine to the 2-methyl-4-chlorodimethylamine salt is 1:20: 30.
4. The topramezone-containing herbicide of claim 1, wherein: the herbicide can be wettable powder, dispersible oil suspending agent, missible oil, water dispersible granules or water suspending agent.
5. The topramezone-containing herbicide of claim 4, wherein: the herbicide is wettable powder.
6. The process for preparing a topramezone-containing herbicide according to claim 5, wherein: adding topramezone, terbuthylazine, 2-methyl-4-chlorodimethylamine salt, a dispersing agent, a wetting agent and a filler into a mixing kettle, uniformly stirring, passing the uniformly mixed material through an airflow crusher, uniformly stirring again through the mixing kettle, sieving the fineness, and subpackaging after all indexes are detected to be qualified to obtain the wettable powder.
7. The process for preparing a topramezone-containing herbicide according to claim 6, wherein: the dispersant is one or more of alkyl naphthalene formaldehyde condensate sulfonate, 2-naphthalene sulfonic acid formaldehyde polymer sodium salt, polycarboxylate, methylene bis (methyl) naphthalene sulfonate and polyether.
8. The process for preparing a topramezone-containing herbicide according to claim 6, wherein: the wetting agent is any one or more of alkyl naphthalene sulfonate, sodium dodecyl sulfate, sodium lignosulfonate, fatty alcohol-polyoxyethylene ether, alkylphenol polyoxyethylene polyoxypropylene ether, fatty alcohol-polyoxyethylene polyoxypropylene ether sulfate and alkylphenol polyoxyethylene polyoxypropylene ether sulfate.
9. The process for preparing a topramezone-containing herbicide according to claim 6, wherein: the filler is one or more of kaolin, bentonite, diatomite, white carbon black, light calcium carbonate and attapulgite.
CN202010313777.9A 2020-04-20 2020-04-20 Topramezone-containing herbicide and preparation method thereof Pending CN111345305A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112724050A (en) * 2020-12-30 2021-04-30 武汉奥克特种化学有限公司 Phosphorus-free alkali-resistant solubilizer and preparation and application thereof

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102334484A (en) * 2011-11-07 2012-02-01 河北博嘉农业有限公司 Herbicide composite
CN102763658A (en) * 2012-08-16 2012-11-07 济南绿邦化工有限公司 Safety herbicide for corn field
CN103430947A (en) * 2011-11-07 2013-12-11 河北博嘉农业有限公司 Topramezone and terbuthylazine compounded herbicide

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102334484A (en) * 2011-11-07 2012-02-01 河北博嘉农业有限公司 Herbicide composite
CN103430947A (en) * 2011-11-07 2013-12-11 河北博嘉农业有限公司 Topramezone and terbuthylazine compounded herbicide
CN102763658A (en) * 2012-08-16 2012-11-07 济南绿邦化工有限公司 Safety herbicide for corn field

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112724050A (en) * 2020-12-30 2021-04-30 武汉奥克特种化学有限公司 Phosphorus-free alkali-resistant solubilizer and preparation and application thereof

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