CN110870478B - Solid preparation containing biphenyl compounds and application thereof - Google Patents
Solid preparation containing biphenyl compounds and application thereof Download PDFInfo
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- CN110870478B CN110870478B CN201811002703.2A CN201811002703A CN110870478B CN 110870478 B CN110870478 B CN 110870478B CN 201811002703 A CN201811002703 A CN 201811002703A CN 110870478 B CN110870478 B CN 110870478B
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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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/10—Sulfones; Sulfoxides
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- Agronomy & Crop Science (AREA)
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Abstract
The invention belongs to the field of acaricides, and relates to a solid preparation containing biphenyl compounds and application thereof. The solid preparation takes the compound A as an active component and is matched with at least one carrier and at least one auxiliary agent, the weight percentage of the compound A of the active component of the solid preparation is 0.5-90%, the auxiliary agent contains a suspending aid, and the weight percentage of the suspending aid is 0.01-5%. According to the invention, under the condition of selecting and matching a proper auxiliary agent system, the auxiliary suspension substance liquiritin is added into the solid preparation in a specific proportion, so that the suspension rate of the solid preparation can be effectively improved, and the interaction between the liquiritin and the structure of the compound A is realized, thereby inhibiting the self defect of softening and dissolving of solid particles, solving the problems of easy melting and softening of low-melting-point raw drug solid preparation particles and low suspension rate in the prior art, ensuring the qualified suspension rate of the solid preparation, ensuring the product performance and realizing unexpected effects.
Description
Technical Field
The invention belongs to the field of acaricides, and relates to a solid preparation containing biphenyl compounds and application thereof.
Background
The biphenyl compound (hereinafter referred to as compound A) disclosed in Chinese invention patent CN 105541682A has excellent acaricidal control effect and wide market application prospect. The structure of compound a is as follows:
as mentioned in the aforementioned patent CN 105541682 a, the compound can be used in the form of dry powder, wettable powder, emulsifiable concentrate, microemulsion, paste, granule, solution, suspension, etc., but the use forms of the compounds described in the patent are prepared in a known manner, for example by diluting or dissolving the active substance with a solvent medium and/or a solid diluent, optionally in the presence of a surfactant, but the choice of the type of use of the compounds known in the art depends on the particular application. Meanwhile, in the process of actually developing pesticide preparation products, the form which can be prepared into the dosage form is generally applicable preparation, the suspension rate of the products cannot be controlled, and a large amount of data prove that the generally applicable preparation has low suspension rate and the suspension rate is reduced obviously under the condition of national standard thermal storage acceleration. Furthermore, solid agricultural chemical preparations can be classified into direct-use solid preparations, dispersible solid preparations and soluble solid preparations according to the national standard GBT19378-2017, and solid preparations are generally convenient to transport, store and handle, so they have been favored in recent years. The solid preparation is diluted with water at the time of use, and solid particles are dissolved and dispersed in various forms, suspended in water, and administered as a liquid medicine. The dispersion and suspension process of the solid preparation is crucial and is a system with good and bad final product performance of the solid preparation. If the liquid medicine is dispersed unevenly after the product is diluted and the suspension performance is not good, the suspension rate is unqualified, and the successful development of the preparation formula can be proved if the suspension rate is not lower than 90 percent according to the suspension rate standard of the current solid preparation. The suspension rate detection method of the solid preparation needs to be carried out according to the national standard GB/T14825.
The compound A is used as a low-melting-point active substance, the melting point of the compound A is 50-60 ℃, after the compound A is prepared into a solid preparation, due to the low-melting-point characteristic of the compound A, particularly in a storage acceleration test, solid particles can be softened, the form is changed, the action of some auxiliary agents, particularly dispersing agents, is weakened, the suspension rate of the preparation can be greatly reduced, the suspension rate is unqualified, and the use of the preparation is finally influenced. Further, there is a need for formulation types and matching systems that address the low suspension rate problem described above.
Disclosure of Invention
The invention aims to provide a solid preparation containing biphenyl compounds and application thereof.
In order to achieve the purpose, the invention adopts the technical scheme that:
a solid preparation containing biphenyl compounds takes a compound A as an active component, and is matched with at least one carrier and at least one auxiliary agent, wherein the weight percentage of the compound A of the active component of the solid preparation is 0.5-90%, and the auxiliary agent contains a suspending aid, wherein the weight percentage of the suspending aid is 0.01-5%.
The addition amount of the suspension aid is 0.05-0.5% by weight.
The suspending aid is liquiritin.
The auxiliary agent in the solid preparation also comprises a wetting dispersant.
The wetting dispersant is one or more of polycarboxylate, lignosulfonate, block copolymer, carboxylate and sulfate.
The solid preparation dosage form is a dispersible solid preparation or a soluble solid preparation.
The solid preparation can be wettable powder, water dispersible granules, dry suspending agents, granules, water dispersible tablets or soluble granules, soluble powder, emulsifiable powder or emulsifiable granules.
The wettable powder comprises 2 to 70 percent of compound A, 1 to 20 percent of wetting dispersant, 0.01 to 5 percent of suspension aid and the balance of carrier according to the mass percentage;
the water dispersible granule comprises 2-70% of compound A, 1-20% of wetting dispersant, 0.01-5% of suspension aid and the balance of carrier by mass percentage;
the dry suspending agent comprises 2-70% of compound A, 5-70% of wetting dispersant, 0.01-5% of suspending aid and the balance of carrier by mass percentage;
the granule comprises 2-70% of compound A, 1-15% of wetting dispersant, 0.01-5% of suspension aid and the balance of carrier by mass percentage;
the water dispersible tablet comprises, by mass, 2-70% of a compound A, 1-20% of a wetting dispersant, 0.01-5% of a suspension aid, 2-20% of a tabletting aid and the balance of a carrier;
the soluble granule comprises 2-70% of compound A, 1-20% of wetting dispersant, 0.01-5% of suspension aid and the balance of carrier by mass percentage;
the soluble powder comprises 2-70% of compound A, 1-20% of wetting dispersant, 0.01-5% of suspension aid and the balance of carrier by mass percentage;
the emulsifiable powder comprises 2-70% of compound A, 1-40% of wetting dispersant, 0.01-5% of suspension aid and the balance of carrier by mass percentage;
the emulsifiable granules comprise 2-70% of compound A, 1-40% of wetting dispersant, 0.01-5% of suspension aid and the balance of carrier by mass percent.
The wetting and dispersing agent includes, but is not limited to, naphthalene formaldehyde condensate sulfonate, fatty alcohol ethylene oxide adduct sulfonate, alkylphenol polyoxyethylene ether sulfonate, polycarboxylate, fatty alcohol ethylene oxide adduct phosphate, alkylphenol polyoxyethylene, ether formaldehyde condensate sulfate, polyoxyethylene polyoxypropylene ether block copolymer, alkylphenol polyoxyethylene phosphate, lignosulfonate, polyoxyethylene alcohol, polyvinylpyrrolidone, sodium polyacrylate, sulfonates, sulfates, carboxylates, phosphates, succinate salts, fatty alcohol polyoxyethylene ether, alkylphenol polyoxyethylene ether, fatty amine polyoxyethylene ether, fatty acid polyoxyethylene ether, acid alcohol ester and polyoxyethylene ether thereof, fatty amide and polyoxyethylene ether thereof, alkanolamide and polyoxyethylene ether thereof, block copolymer, sodium alkylnaphthalene sulfonate polyoxyethylene ether, polyoxyethylene alkyl phenol, polyoxyethylene alkyl ether, polyoxyethylene alkyl naphthalene sulfonate, polyoxyethylene alkyl ether, and polyoxyethylene alkyl ether, Sorbitan fatty acid ester polyoxyethylene ether, polyvinyl alcohol monooleate, fatty alcohol sulfate, alkyl alcohol polyoxyethylene ether sodium sulfate, alkylphenol polyoxyethylene, ether sodium sulfate, alkylphenol polyoxyethylene ether formaldehyde condensate sulfate, alkyl sodium sulfate, alkyl naphthalene sulfonate, fatty alcohol ethylene oxide adduct sulfonate, alkylphenol formaldehyde condensate ethylene oxide adduct sulfonate, alkylamido sulfonate, fatty alcohol polyoxyethylene ether, alkylphenol polyoxyethylene ether, sorbitan fatty acid ester polyoxyethylene ether, polyoxyethylene polyoxypropylene ether block copolymer, alkylphenol formaldehyde condensate polyoxyethylene ether, polyoxyethylene sorbitan ester, polyoxyethylene fatty acid ester, alkyl naphthalene sulfonate sodium fatty alcohol polyoxyethylene ether. Preferably one or more of a polycarboxylate, lignosulfonate, block copolymer, carboxylate, sulphate.
The carrier may be, but is not limited to, one or more of clay, rock flour, chalk, quartz, clay, montmorillonite, sodium sulfate, silica, diatomaceous earth, pumice, gypsum, talc, bentonite, kaolin, attapulgite, precipitated calcium carbonate, china clay, montmorillonite, magnesium aluminum silicate, activated clay, white carbon black, ammonium sulfate, benzofuran resins, perphosphates, alumina, calcite, marble, pumice, and the like. Preferably one or more of clay, rock powder, diatomite, bentonite, kaolin, attapulgite, light calcium carbonate, montmorillonite, activated clay and white carbon black.
The tabletting auxiliary agent can be starch, modified starch, cellulose, modified cellulose, various resins, polyvinylpyrrolidone and the like, and the filler refers to a mixture of one or more fillers.
The solid preparation also comprises common pH regulator, quartz sand, polyvinyl alcohol, glucose, ammonium sulfate, etc. known in the industry. And the preparation process of the solid preparation is as conventional.
The structural formula of the active component compound A is as follows,
in the formula, R1、R2Each independently selected from hydrogen and C1-C8Alkyl, halo C1-C8Alkyl radical, C2-C8Alkenyl, halo C2-C8Alkenyl radical, C2-C8Alkynyl, halo C2-C8Alkynyl, cyano C1-C8Alkyl or cyano halogeno C1-C8An alkyl group; m and n are each independently selected from 0, 1 or 2.
Preferably, the substituents of compound A are as shown in the table below
| Composition comprising a metal oxide and a metal oxide | R1 | R2 | m | n |
| A-1 | CH2CF3 | CH2CF3 | 0 | 1 |
| A-2 | CH2CF3 | CH2CF3 | 1 | 1 |
| A-3 | CH2CF3 | CH2CF3 | 1 | 2 |
| A-4 | CH2CF3 | CH2CF3 | 0 | 0 |
The application of a solid preparation containing biphenyl compounds and the application of the solid preparation as a plant acaricide.
The invention has the advantages that:
the compound A with a lower melting point is used as an active substance to prepare the solid preparation, and the obtained solid preparation solves the problems that the active substance melts into particles with various forms under the national standard specified condition of 54 +/-2 ℃ under the condition of thermal storage acceleration, and the particle form changes after the room temperature is recovered, so that the dispersion and suspension performance of the particles is influenced, and the suspension rate is greatly reduced. Furthermore, according to the invention, under the condition of selecting and matching a proper auxiliary agent system, liquiritin serving as a suspension aid is added into the solid preparation, and a specific addition amount is given, so that the suspension rate of the solid preparation can be effectively improved, and the interaction of the liquiritin and the structure of the compound A is realized, thereby inhibiting the self defect of softening and dissolving of solid particles, solving the problems of easy melting and softening of low-melting-point original drug solid preparation particles and low suspension rate in the prior art, ensuring the qualified suspension rate of the solid preparation, ensuring the product performance and realizing unexpected effects.
Detailed Description
The following specific examples are intended to illustrate the invention in further detail, but the invention is by no means limited to these examples, and methods known to those skilled in the art are included within the scope of the invention.
The acaricide solid preparation adopts the matching of the auxiliary agent system and the interaction of the raw pesticide, so that the suspension performance of the solid preparation is greatly improved and the suspension rate is qualified by the compatibility of the auxiliary agent system and the addition of the auxiliary suspension substance under the storage condition.
The percentages and parts in the following formulations are by weight. The active component compound A is prepared according to the record of the prior art (the content is 93-99%) and added after being folded, the proportion of each component is weight percent, and other raw materials are all commercial products. The structure of the compound A used is shown in Table 1.
TABLE 1 Structure of Compound A
EXAMPLE 1.20% preparation of wettable powder of Compound A-1
And (3) supplementing 100% of compound A-120%, 5% of calcium lignosulphonate, 5% of D-4253%, 5% of white carbon black and the balance of light calcium carbonate to obtain 20% of compound A-1 wettable powder with good physical properties.
EXAMPLE 2.20% preparation of Compound A-1 wettable powder
The 20 percent compound A-1 wettable powder with good physical property can be obtained by adding 100 percent of compound A-120 percent, 5 percent of calcium lignosulphonate, 5 percent of D-4253 percent of white carbon black, 0.1 percent of liquiritin and the balance of light calcium carbonate.
EXAMPLE 3.30% formulation of Compound A-2 granules
Mixing the compound A-230% and diatomite 8% to obtain mother powder, and then adding 5% PVA and quartz sand to mix to obtain 30% compound A-2 granules with good physical properties.
Example 4.30% formulation of Compound A-2 granules
Mixing the compound A-230%, liquiritin 0.2% and diatomite 8% to obtain mother powder, and then adding 5% PVA and quartz sand to mix to obtain 30% compound A-2 granules with good physical properties.
Example 5.40% formulation of Compound A-3 soluble granules
The 40% compound A-3 soluble granules with good physical properties can be obtained by completely supplementing compound A-340%, Morwet D4255%, Morwet EFW 2%, sodium sulfate 20%, glucose 8%, sucrose 2% and ammonium sulfate.
Example 6.40% formulation of Compound A-3 soluble granules
The 40% compound A-3 soluble granules with good physical properties can be obtained by completely supplementing compound A-340%, Morwet D4255%, Morwet EFW 2%, liquiritin 0.3%, sodium sulfate 20%, glucose 8%, sucrose 2% and ammonium sulfate.
EXAMPLE 7.50% preparation of Compound A-4 Dry suspension
The preparation method comprises the following steps of supplementing the compound A-450%, DF 222210%, lignosulfonate 20% and water to 100%, carrying out sand mill wet sanding to obtain a suspension, and further carrying out spray drying to obtain the 50% compound A-4 dry suspending agent with good physical properties.
EXAMPLE 8.50% preparation of Compound A-4 Dry suspension
The preparation method comprises the following steps of supplementing the compound A-450%, DF 222210%, lignosulfonate 20%, liquiritin 0.3% and water to 100%, carrying out wet sanding by a sand mill to obtain suspension, and further carrying out spray drying to obtain 50% of compound A-4 dry suspending agent with good physical properties.
Example 9.70% preparation of Compound A-4 Water dispersible granules
The compound A-470%, Morwet EFW 1.5%, sodium salt of alkyl naphthalene sulfonic acid polycondensate 3%, soluble starch 10%, sodium sulfate 8% and bentonite are complemented to 100%, and 70% of compound A-4 water dispersible granules with good physical properties can be obtained.
Example 10.70% preparation of Compound A-4 Water dispersible granules
The 70% compound A-4 water dispersible granule with good physical properties can be obtained by complementing compound A-270%, Morwet EFW 1.5%, sodium salt of alkyl naphthalene sulfonic acid polycondensate 3%, soluble starch 10%, sodium sulfate 8%, liquiritin 0.2% and bentonite to 100%.
The suspension percentage of the above examples was determined according to the method mentioned in the national standard GB/T14825, specifically by accurately weighing 1.5g (to 0.0002g) of the solid preparation sample and determining according to "method 1" of GB/T14825. Transferring the rest 25mL of suspension and precipitate into a 100mL volumetric flask, washing twice with 10mL of methanol each time, adding the washing solution into the volumetric flask, adding methanol to constant volume, degassing in an ultrasonic bath for 10min, and cooling to the liquid level and returning to the scale. Centrifuging, collecting supernatant, determining the mass of effective components by high performance liquid chromatography, and calculating the suspension ratio X (see Table 2), wherein the suspension ratio formula is as follows:
in the formula, m1-mass of active ingredient in sample, g, taken to prepare suspension;
m2-the mass of active ingredient, g, remaining in 25mL of suspension at the bottom of the graduated cylinder;
TABLE 2 results of suspension ratio measurement
As can be seen from Table 2, due to the low melting point of Compound A, the suspension percentage of the solid preparation of Compound A is low, and particularly after the accelerated heat storage test, the suspension percentage is reduced remarkably. However, in the examples 2, 4, 6, 8 and 10, the suspension condition of the preparation is obviously improved, the bottom sediment is obviously reduced, the suspension rate is increased, the suspension condition of the thermal storage acceleration test is good, and the suspension rate is greatly improved after the liquiritin is added. For solid preparations, the quality of suspension directly influences the suspension rate of the product and finally improves the corresponding activity, but the liquiritin which is a substance for improving the suspension performance is added into the solid preparation, and the liquiritin interacts with the structure of the compound A, so that the problem that the structure of the compound A is softened under the storage condition due to lower melting point can be effectively controlled, and the suspension condition of the solid preparation is controlled under the condition of proper compatibility of an auxiliary system, so that the problem of low suspension rate of the low-melting-point compound in the prior art is solved, and the practical significance is brought to the application of the solid preparation product.
Claims (8)
1. A solid preparation containing biphenyl compounds takes a compound A as an active component, and is matched with at least one carrier and at least one auxiliary agent, and is characterized in that: the weight percentage of the active component compound A of the solid preparation is 0.5 to 90 percent, and the auxiliary agent contains a suspending aid, wherein the weight percentage of the suspending aid is 0.01 to 5 percent;
the structural formula of the active component compound A is as follows,
in the formula, R1、R2Each independently selected from halogeno C1-C8An alkyl group; m and n are independently selected from 0, 1 or 2; the suspending aid is liquiritin.
2. The solid preparation containing a biphenyl compound according to claim 1, wherein: the addition amount of the suspension aid is 0.05-0.5% by weight.
3. The solid preparation containing a biphenyl compound according to any one of claims 1 or 2, wherein: the auxiliary agent in the solid preparation also comprises a wetting dispersant.
4. The solid preparation containing biphenyls as claimed in claim 3, wherein: the wetting dispersant is one or more of polycarboxylate, lignosulfonate, block copolymer, carboxylate and sulfate.
5. The solid preparation containing a biphenyl compound according to claim 1, wherein: the solid preparation dosage form is a dispersible solid preparation or a soluble solid preparation.
6. The solid preparation containing biphenyls as claimed in claim 5, wherein: the solid preparation can be wettable powder, water dispersible granules, dry suspending agents, granules, water dispersible tablets or soluble granules, soluble powder, emulsifiable powder or emulsifiable granules.
7. The solid preparation containing biphenyls as claimed in claim 6, wherein:
the wettable powder comprises 2 to 70 percent of compound A, 1 to 20 percent of wetting dispersant, 0.01 to 5 percent of suspension aid and the balance of carrier according to the mass percentage;
the water dispersible granule comprises 2-70% of compound A, 1-20% of wetting dispersant, 0.01-5% of suspension aid and the balance of carrier by mass percentage;
the dry suspending agent comprises 2-70% of compound A, 5-70% of wetting dispersant, 0.01-5% of suspending aid and the balance of carrier by mass percentage;
the granule comprises 2-70% of compound A, 1-15% of wetting dispersant, 0.01-5% of suspension aid and the balance of carrier by mass percentage;
the water dispersible tablet comprises, by mass, 2-70% of a compound A, 1-20% of a wetting dispersant, 0.01-5% of a suspension aid, 2-20% of a tabletting aid and the balance of a carrier;
the soluble granule comprises 2-70% of compound A, 1-20% of wetting dispersant, 0.01-5% of suspension aid and the balance of carrier by mass percentage;
the soluble powder comprises 2-70% of compound A, 1-20% of wetting dispersant, 0.01-5% of suspension aid and the balance of carrier by mass percentage;
the emulsifiable powder comprises 2-70% of compound A, 1-40% of wetting dispersant, 0.01-5% of suspension aid and the balance of carrier by mass percentage;
the emulsifiable granules comprise 2-70% of compound A, 1-40% of wetting dispersant, 0.01-5% of suspension aid and the balance of carrier by mass percent.
8. The use of the solid preparation containing biphenyl compounds according to claim 1, wherein: the application of the solid preparation as a plant acaricide.
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| CN110870476B (en) * | 2018-08-30 | 2021-10-01 | 沈阳中化农药化工研发有限公司 | Liquid preparation containing biphenyl compounds and application thereof |
| AU2022216691A1 (en) * | 2021-02-05 | 2023-08-24 | Shenyang University Of Chemical Technology | Biphenyl compound containing sulfide (sulfoxide) substitution and use thereof |
| CN116158429B (en) * | 2021-11-25 | 2024-06-18 | 沈阳中化农药化工研发有限公司 | Stable liquid preparation containing biphenyl compounds |
| CN116158428A (en) * | 2021-11-25 | 2023-05-26 | 沈阳中化农药化工研发有限公司 | Liquid preparation containing biphenyl structure |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1314085A (en) * | 2000-03-17 | 2001-09-26 | 韩尚吉 | Natural fruit sugar enriching agent and preparing method thereof |
| CN105541682A (en) * | 2014-10-24 | 2016-05-04 | 沈阳中化农药化工研发有限公司 | Biphenyl compound and application thereof |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1314085A (en) * | 2000-03-17 | 2001-09-26 | 韩尚吉 | Natural fruit sugar enriching agent and preparing method thereof |
| CN105541682A (en) * | 2014-10-24 | 2016-05-04 | 沈阳中化农药化工研发有限公司 | Biphenyl compound and application thereof |
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