CN113519538A - Bactericidal composition preparation and application thereof - Google Patents

Bactericidal composition preparation and application thereof Download PDF

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Publication number
CN113519538A
CN113519538A CN202010320441.5A CN202010320441A CN113519538A CN 113519538 A CN113519538 A CN 113519538A CN 202010320441 A CN202010320441 A CN 202010320441A CN 113519538 A CN113519538 A CN 113519538A
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Prior art keywords
compound
preparation
tebuconazole
suspending agent
triazole
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Inventor
丑靖宇
董广新
李天一
单忠刚
遇璐
王刚
李斌
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Jiangsu Yangnong Chemical Co Ltd
Shenyang Sinochem Agrochemicals R&D Co Ltd
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Jiangsu Yangnong Chemical Co Ltd
Shenyang Sinochem Agrochemicals R&D Co Ltd
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Priority to CN202010320441.5A priority Critical patent/CN113519538A/en
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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
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles

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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 belongs to the field of bactericides and discloses a bactericidal preparation of a composition taking pyrazole amide compounds (hereinafter referred to as compound A) and triazole bactericides as active components and application thereof. The mass ratio of the two active components is 1:50-50:1, and the weight content of the active components in the composition is 10-80%. The composition comprises at least one carrier and at least one adjuvant. The composition can be prepared into missible oil, aqueous emulsion, microemulsion, suspending agent, suspoemulsion, dispersible oil suspending agent, wettable powder, water dispersible granule, dry suspending agent and other formulations. The preparation variety of the invention has excellent control effect on plant diseases caused by ascomycotina, basidiomycotina and deuteromycotina, and is safe to crops. Wherein the structural formula of the compound A is shown as the following formula, wherein R1Selected from hydrogen or methyl; r2Selected from methyl,Ethyl, propyl or isopropyl.

Description

Bactericidal composition preparation and application thereof
Technical Field
The invention belongs to the field of bactericides and relates to a bactericidal composition (containing pyrazole amide compound A and triazole bactericides) preparation and application thereof.
Background
At the present stage, the fungicide variety containing a single active ingredient has defects of different degrees in the process of preventing and treating fungal diseases: the long-term use of the bactericidal composition can easily cause the fungi to generate drug resistance, reduce the drug effect, fail to play a good control effect and have a narrow bactericidal spectrum range. Through compounding of two or more active components, the bactericidal effect can be enhanced, the service life of the medicament can be prolonged, the bactericidal spectrum can be expanded, the control effect can be improved, and the pollution to the environment can be reduced.
However, pesticides themselves are a special class of biologically active chemicals, and the selection of active ingredients and the adjuvant system to which they are matched is necessary in order to confer optimum efficacy to the active ingredient, although the formulation has a corresponding effect. According to different use methods and crops, a proper active combination and an auxiliary agent matched with the active combination are selected and then prepared into a corresponding preparation for application so as to improve the biological activity of the pesticide, reduce the dosage, reduce the cost and reduce the pollution to the environment. Wherein, the mutual matching of active ingredient raw medicines in the preparation is crucial, then different auxiliary agent systems are further matched according to different raw medicines when the preparation is prepared, and the auxiliary agent systems and the raw medicines are interacted so as to improve the pesticide effect. In the prior art, no report is found about the preparation of the compound.
Disclosure of Invention
The invention aims to solve the problems of resistance possibly caused by using a single agent of the compound A, reduction of drug effect and the like, and provides a bactericidal composition (containing pyrazole amide compound A and triazole bactericide) preparation and application thereof.
In order to realize the purpose of the invention, the technical scheme of the invention is as follows:
a sterilization composition preparation comprises active components of a compound A and a triazole bactericide, wherein the mass ratio of the two active components is 1:50-50: 1; the triazole bactericide is selected from: one or more of tebuconazole, propiconazole, difenoconazole, epoxiconazole, triadimefon, prothioconazole, flusilazole, diniconazole, myclobutanil, diniconazole, penconazole, hexaconazole, triadimenol, cyproconazole, fluquinconazole, flutriafol, metconazole, imibenconazole, ipconazole, triticonazole, bitertanol, epoxiconazole, tetraconazole, imazalil, tetraconazole, simeconazole or triflumizole; the structural formula of the compound A is shown as follows,
Figure BDA0002461190860000021
in the formula, R1Selected from hydrogen or methyl; r2Selected from methyl, ethyl, propyl or isopropyl.
Preferably, the triazole fungicide is selected from tebuconazole, propiconazole, difenoconazole, epoxiconazole, triadimefon, prothioconazole, flusilazole, myclobutanil, diniconazole, penconazole, triadimenol, cyproconazole, flutriafol, imibenconazole, triticonazole or tetraconazole.
Tebuconazole: (RS) -1- (4-chlorophenyl) -4, 4-dimethyl-3- (1H-1,2,4 triazol-1-ylmethyl) pentan-3-ol;
propiconazole: 1- [2- (2, 4-dichlorophenyl) -4-propyl-1, 3-dioxolan-2-methyl ] -1-hydro-1, 2, 4-triazole;
difenoconazole: cis, trans-3-chloro-4- [ 4-methyl-2-1H-1, 2, 4-triazol-1-ylmethyl) -1, 3-dithiapentan-2-yl) phenyl 4-chlorophenyl ether;
epoxiconazole: (2RS,3RS) -1- [3- (2-chlorophenyl) -2, 3-epoxy-2- (4-fluorophenyl) propyl [ -1H-1,2, 4-triazole;
triazolone: 1-mono (4-chlorophenoxy) -3, 3-dimethyl-1-mono (1H-1,2, 4-triazol-l-yl) - α -butanone;
prothioconazole: 2- (2- (1-chlorocyclopropyl) -3- (2-chlorophenyl) -2-hydroxypropyl-1-2-dihydro-3-1, 2, 4-triazole-3-thioxo;
flusilazole: bis (4-fluorophenyl) methyl (1H-1,2, 4-oxazol-l-ylmethylene) silane;
myclobutanil: 1- (4-chlorophenyl) -2- (1H-1,2, 4-triazole-1-methyl) hexanenitrile; 2- (4-chlorophenyl) -2- (1H,1,2, 4-triazole-1-methyl) hexanenitrile;
diniconazole: (E) - (RS) -1- (2, 4-dichlorophenyl) -4, 4-dimethyl-2- (1H-1,2, 4-triazol-1-yl) pent-1 en-3-ol;
penconazole: 1- [2- (2, 4-dichlorophenyl) pentyl ] -1H-1,2, 4-triazole;
triadimenol: 1-mono (4-chlorophenoxy) -3, 3-dimethyl-1-mono (1H-1,2, 4-triazol-l-yl) -2-butanol;
cyproconazole: (2RS,3 RS; 2RS,3SR) -2- (4-chlorophenyl) -3-cyclopropyl-1- (1H-1,2, 4-triazol-1-yl) butan-2-ol;
flutriafol: (RS) -2,4' -difluoro-a- (1H-1,2, 4-triazole-1-methyl) benzhydrol;
imibenconazole: 4-chlorobenzyl N- (2, 4-chlorophenyl) -2(1H l, 2,4 oxazol-l-yl) thioacetamide ester;
sterilizing and azole: (RS) - (E) -5- (4-chlorobenzylidene) -2, 2-dimethyl-1 (1H-1,2, 4-triazol-1-ylmethyl) cyclopentanol;
tetraconazole: 2- (2, 4-dichlorophenyl) -3- (1H-1,2, 4-triazol-1-yl) propyl 1,1,2,2, -tetrafluoroethyl ether.
The mass ratio of the compound A in the active component to the triadimefon, the triadimenol, the cyproconazole or the flutriafol in the triazole fungicide is 1:25-25: 1;
the mass ratio of the compound A in the active ingredients to tebuconazole, propiconazole, difenoconazole, epoxiconazole, imibenconazole or triticonazole in the triazole fungicide is 1:20-20: 1;
the mass ratio of the compound A in the active ingredient to prothioconazole, flusilazole, myclobutanil, penconazole or tetraconazole in the triazole fungicide is 1:10-10: 1.
Preferably, the compound a has the structural formula: r1 is selected from methyl; r2 is selected from propyl.
The dosage form of the bactericide preparation is missible oil, aqueous emulsion, microemulsion, suspending agent, suspoemulsion, dispersible oil suspending agent, wettable powder, water dispersible granule and dry suspending agent.
The preparation comprises an active ingredient, at least one auxiliary agent and at least one carrier; wherein the active ingredients in the preparation account for 10-80% of the mass of the preparation.
The auxiliary agent comprises an emulsifier and a wetting dispersant; in addition, thickeners, antifoams, preservatives, pH regulators may be included, but are not required. The carrier is a dispersion medium.
The dispersion medium includes oil, an organic solvent or water.
The thickener can be one or more of xanthan gum, hydroxymethyl cellulose, sodium hydroxymethyl cellulose, hydroxyethyl cellulose, methyl cellulose, magnesium aluminum silicate, polyvinyl alcohol, polyethylene glycol, starch, white carbon black, and organic bentonite.
The defoaming agent can be defoaming agent SAG1522, silicone, C8～10Fatty alcohol, phosphoric acid esters, C10～20Saturated fatty acids (such as capric acid) and amide or one or more of the other.
The preservative can be one or more of sodium benzoate, cason (2-methyl-4-isothiazoline-3-ketone and (B) 5-chloro-2-methyl-4-isothiazoline-3-ketone), potassium sorbate, sodium dehydroacetate or the like.
The recorded liquid preparation is missible oil, aqueous emulsion, microemulsion, suspending agent, suspoemulsion and dispersible oil suspending agent;
the missible oil comprises an active component, an emulsifier and a solvent; according to weight percentage, 1-90% of active component, 1-30% of emulsifier and 1-98% of solvent;
the aqueous emulsion, the microemulsion and the suspoemulsion comprise active components, an emulsifier, an antifreezing agent, a solvent and a carrier; the active component accounts for 1-90 percent, the emulsifier accounts for 1-20 percent, the antifreezing agent accounts for 1-30 percent, the solvent accounts for 1-30 percent, the thickening agent accounts for 0.1-5 percent, and the carrier accounts for 1-60 percent;
wherein the emulsifier in the missible oil, the aqueous emulsion, the microemulsion and the suspoemulsion is one or more of fatty alcohol-polyoxyethylene ether, alkylphenol ethoxylate, polyoxyethylene sorbitan ester, polyoxyethylene fatty acid ester, block copolymer, alkyl naphthalene sulfonate, fatty alcohol-polyoxyethylene ether, calcium alkylbenzene sulfonate, styrene polyoxyethylene ether ammonium sulfate salt, phenethyl phenol polyoxypropylene ether, No. 506, No. 600, No. 0201B, 0203B, 2201, No. 700, NP-10 phosphate, OP-10 phosphate, castor oil polyoxyethylene ether, span 80, Tween 80 and No. 602;
further optionally, the emulsifier in the emulsifiable concentrate is: 0201B, 0203B, 500#, 600#, 700#, Tween-20.
The emulsifier in the aqueous emulsion and the suspoemulsion is as follows: castor oil polyoxyethylene ether (EL-20), 0201B, polyoxyethylene (n20) phenethyl phenol ether oleate and Tween-80.
The emulsifier in the microemulsion is as follows: one or more of AEO-3, 0203B, 700#, Tween-85.
The solvents in the missible oil, the aqueous emulsion, the microemulsion and the suspoemulsion are as follows: solvent oil, toluene, xylene, methanol, ethanol, methyl oleate, cyclohexanone, vegetable oil, dimethylformamide, acetonitrile, polyethylene glycol, pelargonide, tributyl phosphate, butyrolactone, N-long-chain alkyl pyrrolidone and/or liquid paraffin.
Further optionally, the solvent is one or more of mineral spirit, xylene, methanol, ethanol, methyl oleate, cyclohexanone, vegetable oil, dimethylformamide, pelargoniamide, tributyl phosphate, butyrolactone and liquid paraffin.
The antifreeze in the aqueous emulsion, the microemulsion and the suspoemulsion is one or more of ethylene glycol, glycerol, propylene glycol, urea, methanol, ethanol, isopropanol, diethylene glycol, ethylene glycol butyl ether, propylene glycol butyl ether, ethylene glycol butyl ether acetate, dimethyl sulfoxide, calcium chloride, sodium acetate, magnesium chloride and thiourea.
Further optionally, the antifreeze is one or more of ethylene glycol, glycerol, propylene glycol and urea.
The carrier in the aqueous emulsion, the microemulsion and the suspoemulsion is water.
The suspending agent and the dispersible oil suspending agent comprise active components, wetting dispersing agents and dispersing media; according to weight percentage, 1-90% of active component, 1-20% of wetting dispersant and 1-99% of dispersion medium;
the wetting dispersant in the suspending agent and the dispersible oil suspending agent is alkyl 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, sulfonate, sulfate, carboxylate, phosphate salt, succinate salt, fatty alcohol polyoxyethylene ether, alkylphenol polyoxyethylene, 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, fatty alcohol polyoxyethylene ether, polyoxyethylene alkyl ether, fatty acid polyoxyethylene ether, acid alcohol ester and polyoxyethylene ether thereof, fatty amide and polyoxyethylene ether thereof, fatty acid amide and polyoxyethylene alkyl ether thereof, block copolymer, polyoxyethylene alkyl ether, polyoxyethylene ether, fatty acid ester and polyoxyethylene ether thereof, or polyoxyethylene alkyl ether, One or more of alkyl sodium naphthalene sulfonate, fatty alcohol polyoxyethylene ether, sorbitan fatty acid ester polyoxyethylene ether and polyvinyl alcohol monooleate;
further optionally, the wetting and dispersing agent in the suspending agent is: one or more of polycarboxylate, lignosulfonate, block copolymer, carboxylate, sulfate.
The wetting dispersant in the dispersible oil suspending agent is as follows: polyvinyl alcohol monooleate, AEO-3, T-80, 1601 and Span-80.
The dispersion medium of the suspending agent is water.
The dispersing medium of the dispersible oil suspending agent is one or more of solvent oil, dimethylbenzene, methanol, vegetable oil, methyl oleate, dimethylformamide, pelargonide, tributyl phosphate, butyrolactone and liquid paraffin.
Further optionally, the dispersing medium of the dispersible oil suspending agent is one or more of solvent oil, methanol, vegetable oil, methyl oleate, pelargonide, tributyl phosphate, butyrolactone and liquid paraffin.
Compared with the liquid preparation in the prior art, the solid preparation provided by the invention realizes the development of preparation samples by adopting different technical means, combines the physical and chemical properties of active components, and completes the development and research of the composition for the solid preparation through the characteristic research of different solid preparation devices and auxiliaries, thereby obtaining better preparation effect.
The solid preparation comprises wettable powder, water dispersible granules, dry suspending agent and the like.
The wettable powder, the water dispersible granule and the dry suspending agent comprise active components, wetting dispersant and carrier; the active component accounts for 1-90 percent, the wetting dispersant accounts for 1-40 percent and the carrier accounts for 1-99 percent.
The wetting dispersant in the wettable powder, the water dispersible granule and the dry suspending agent is fatty alcohol sulfate, alkyl alcohol 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 fatty alcohol polyoxyethylene ether, alkyl naphthalene formaldehyde condensate sulfonate, fatty alcohol ethylene oxide adduct sulfonate, fatty alcohol polyoxyethylene ether, alkyl naphthalene sulfonate, polyoxyethylene alkyl ether, polyoxyethylene alkyl naphthalene sulfonate, polyoxyethylene alkyl polyoxyethylene ether, polyoxyethylene alkyl ether, alkyl polyoxyethylene ether, alkyl polyoxyethylene ether, alkyl sulfate, polyoxyethylene ether, alkyl polyoxyethylene ether, alkyl sulfate, polyoxyethylene ether, alkyl ether, polyoxyethylene ether, sorbitan ester, sorbitan, 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, sulfonate, sulfate, carboxylate, one or more of phosphate salts, succinate salts, fatty alcohol-polyoxyethylene ether, alkylphenol ethoxylates, 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 alkyl naphthalene sulfonate-fatty alcohol polyoxyethylene ether, sorbitan fatty acid ester polyoxyethylene ether and polyvinyl alcohol monooleate;
further optionally, the wetting dispersant in the wettable powder is one or more selected from fatty alcohol sulfate, alkyl alcohol polyoxyethylene ether sodium sulfate, alkylphenol polyoxyethylene ether, alkyl sodium sulfate, alkyl naphthalene sulfonate, fatty alcohol ethylene oxide adduct sulfonate, fatty alcohol polyoxyethylene ether, alkylphenol polyoxyethylene ether, polyoxyethylene polyoxypropylene ether block copolymer, polycarboxylate, lignosulfonate, block copolymer and carboxylate.
The wetting dispersant in the water dispersible granule is one or more of polycarboxylate, lignosulfonate, block copolymer, carboxylate and sulfate.
The wetting dispersant in the dry suspending agent is one or more of polycarboxylate, ether formaldehyde condensate sulfate, polyoxyethylene polyoxypropylene ether block copolymer, alkylphenol polyoxyethylene phosphate, lignosulfonate, polyvinylpyrrolidone, sodium polyacrylate, sulfonate, carboxylate and phosphate salt.
The carrier in the wettable powder, the water dispersible granule and the dry suspending agent is one or more of clay, rock powder, chalk, quartz, clay, montmorillonite, sodium sulfate, silicon dioxide, diatomite, pumice, gypsum, talc, bentonite, kaolin, starch, soluble starch, attapulgite, light calcium carbonate, pottery clay, montmorillonite, magnesium aluminum silicate, activated clay, white carbon black, ammonium sulfate, benzofuran resin, superphosphate, alumina, calcite, marble, pumice and the like.
Further optionally, the carrier is one or more of clay, rock powder, diatomite, bentonite, kaolin, attapulgite, light calcium carbonate, montmorillonite, activated clay and white carbon black.
The application of the bactericidal preparation is that the bactericidal preparation is used as a bactericide for plant diseases caused by ascomycotina, basidiomycotina and deuteromycotina.
The invention has the advantages that:
1. the active ingredients of the preparation of the invention mutually show excellent synergy within a certain proportion range, and compared with a single preparation, the mixed active ingredients obviously improve the sterilization effect, thereby reducing the dosage, reducing the medication cost of farmers and simultaneously reducing the influence degree on the environment.
2. The bactericidal spectrum is expanded, and the bactericidal preparation can simultaneously prevent and treat various crop diseases, thereby providing an extremely convenient and effective pesticide application means. The bactericidal composition has a good effect of treating diseases simultaneously occurring on various plants, such as tomato gray mold, leaf mold, early blight, cucumber downy mildew, scab, powdery mildew, apple alternaria leaf spot, wheat powdery mildew, rust disease, banded sclerotial blight, gibberellic disease, grape white rot and the like.
3. The application of the preparation can delay the generation and development of the resistance of a single agent.
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 percentages and parts in the formula are by weight. The active component compound A is prepared according to the record of the prior art (the content is 90-99%) and added after being folded, the proportion of each component is weight percent, and other raw materials are all commercial products.
In the following formulation examples, compound a has the following structure: r1 is selected from methyl; r2 is selected from propyl.
Formulation examples of formulations
1. Preparation of emulsifiable concentrate
EXAMPLE 1.10% preparation of Compound A. Tebuconazole emulsifiable concentrate
According to the formula requirement, 5% of compound A, 5% of tebuconazole, 8% of 0203B, 500# 1%, 5% of cyclohexanone and solvent oil S-150 are added into a mixing kettle until the mixture is 100%, the mixture is uniformly stirred and mixed, and if necessary, the mixture is heated and dissolved by a hot water bath, so that 10% of compound A-tebuconazole missible oil can be obtained.
EXAMPLE 2.30% preparation of Compound A propiconazole emulsifiable concentrate
According to the formula requirement, 10% of compound A, 20% of propiconazole, 10% of 700#, 5% of 600#, 5% of dimethylformamide and solvent oil S-200 are added into a mixing kettle until the mixture is 100%, the mixture is uniformly stirred and mixed, and if necessary, the mixture is heated and dissolved by a hot water bath, so that 30% of compound A-propiconazole missible oil can be obtained.
EXAMPLE 3.25% preparation of Compound A.Myclobutanil emulsifiable concentrate
According to the formula requirement, 5% of compound A, 20% of myclobutanil, 5% of 0201B, 22015%, 5% of dimethylformamide and solvent oil S-150 are added into a mixing kettle until the mixture is 100%, the mixture is uniformly stirred and mixed, and if necessary, the mixture is heated and dissolved by a hot water bath, so that 25% of compound A-myclobutanil missible oil is obtained.
EXAMPLE 4.30% preparation of Compound A.Triazolol emulsifiable concentrate
According to the formula requirement, 5% of compound A, 25% of triadimenol, 15% of 0201B, 500# 3%, 5% of dimethylformamide, 5% of cyclohexanone and solvent oil S-150 are added into a mixing kettle until the mixture is 100%, the mixture is uniformly stirred and mixed, and if necessary, the mixture is heated and dissolved by a hot water bath, so that 30% of compound A-triadimenol emulsifiable concentrate can be obtained.
2. Preparation of aqueous emulsion
EXAMPLE 5.15% preparation of Compound A Tebuconazole aqueous emulsion
According to the formula requirement, 5% of compound A, 10% of tebuconazole, 4% of T-8010%, S-801%, 500# 4%, 4% of ethylene glycol and 5% of pelargonide are added into a mixing kettle, stirred and mixed to be dissolved into a uniform oil phase, and the rest of deionized water (which is complemented to 100%) is added into the oil phase under high-speed shearing, so that the 15% compound A-tebuconazole aqueous emulsion with good dispersibility can be obtained.
Example 6.15% preparation of aqueous emulsion of Compound A-triadimenol
According to the formula requirements, 5% of compound A, 10% of triadimenol, EL-202%, 16012%, 500# 1%, 4% of ethylene glycol, 5% of pelargonamide and 5% of cyclohexanone are added into a mixing kettle, stirred and mixed to be dissolved into a uniform oil phase, and under high-speed shearing, the rest of deionized water (which is supplemented to 100%) is added into the oil phase, so that the 15% compound A-triadimenol water emulsion with good dispersibility can be obtained.
Example 7.20% formulation of Compound A. Difenoconazole aqueous emulsion
According to the formula requirement, 5% of compound A, 15% of difenoconazole, 4% of 700#, S-803%, 500# 1%, 4% of ethylene glycol and 10% of pelargonide are added into a mixing kettle, stirred and mixed to be dissolved into a uniform oil phase, and the rest of deionized water (which is complemented to 100%) is added into the oil phase under high-speed shearing, so that the 20% compound A-difenoconazole aqueous emulsion with good dispersibility can be obtained.
EXAMPLE 8.30% preparation of Compound A Prothioconazole aqueous emulsion
According to the formula requirement, 5% of compound A, 25% of prothioconazole, 6% of 600# S, T-202% of S-801%, 1% of 500# S, 4% of ethylene glycol and 20% of pelargonamide are added into a mixing kettle, stirred and mixed to be dissolved into a uniform oil phase, and the rest of deionized water (which is complemented to 100%) is added into the oil phase under high-speed shearing, so that the 30% compound A-prothioconazole aqueous emulsion with good dispersibility can be obtained.
3. Preparation of microemulsion
Example 9.12% formulation of Compound A.Tebuconazole microemulsion
According to the formula requirement, adding 3% of compound A, 9% of tebuconazole, 5% of 0201B, 3% of 601# compound, 5% of pelargonide, 10% of deionized water, 4% of glycerol and the balance of S-150 (the balance is up to 100%) into a mixing kettle, stirring and mixing to dissolve the mixture into a uniform oil phase, and obtaining the 12% compound A.tebuconazole microemulsion with good dispersibility.
EXAMPLE 10.15% preparation of Compound A propiconazole microemulsion
According to the formula requirement, 5% of compound A, 10% of propiconazole, 5% of 0201B, 3% of 601# compound, 10% of pelargonide, 10% of deionized water, 4% of glycerol and the balance of S-150 (the balance is up to 100%) are added into a mixing kettle, stirred and mixed, and dissolved into a uniform oil phase, so that the 15% compound A-propiconazole microemulsion with good dispersibility can be obtained.
4. Preparation of suspending agent
Example 11.20% preparation of Compound A. Tebuconazole suspension
According to the formula requirement, adding 4% of compound A, 16% of tebuconazole, 16% of W-6001%, D8654%, 1% of magnesium aluminum silicate, 0.2% of xanthan gum, 4% of ethylene glycol and the balance of deionized water (the balance is up to 100%) into a high-shear mixing kettle, shearing and mixing, and then sanding by using a sand mill to obtain the 20% of compound A.tebuconazole suspending agent with good dispersibility.
EXAMPLE 12.20% preparation of Compound A. Tebuconazole suspension
According to the formula requirement, adding 4% of compound A, 16% of tebuconazole, 16012% of NNO 3%, 1% of magnesium aluminum silicate, 0.2% of xanthan gum, 4% of ethylene glycol and the balance of deionized water (the balance is up to 100%) into a high-shear mixing kettle, shearing and mixing, and then sanding by using a sand mill to obtain the 20% of compound A. flutriafol suspending agent with good dispersibility.
Example 13.30% preparation of Compound A. Tebuconazole suspension
According to the formula requirement, adding 5% of compound A, 25% of tebuconazole, W-6001%, D8654%, 1% of magnesium aluminum silicate, 0.2% of xanthan gum, 4% of ethylene glycol and the balance of deionized water (the balance is up to 100%) into a high-shear mixing kettle, shearing and mixing, and then sanding by using a sand mill to obtain the 30% compound A.tebuconazole suspending agent with good dispersibility.
Example 14.15% formulation of Compound A. Difenoconazole suspension
According to the formula requirement, adding 3% of compound A, 12% of difenoconazole, 2% of EFW, 4% of D4255%, 2% of magnesium aluminum silicate, 0.1% of xanthan gum, 4% of ethylene glycol and the balance of deionized water (the balance is up to 100%) into a high-shear mixing kettle, shearing and mixing, and then sanding by using a sand mill to obtain the 15% compound A-difenoconazole suspending agent with good dispersibility.
Example 15.20% preparation of Compound A. Fluconazole suspension
According to the formula requirement, adding 5% of compound A, 15% of epoxiconazole, W-6002%, 33SC 5%, 2% of magnesium aluminum silicate, 0.1% of xanthan gum, 4% of ethylene glycol and the balance of deionized water (the balance is up to 100%) into a high-shear mixing kettle, shearing and mixing, and then sanding by using a sand mill to obtain the 20% compound A. epoxiconazole suspending agent with good dispersibility.
EXAMPLE 16.25% formulation of Compound A.triazolone suspension
According to the formula requirement, adding 5% of compound A, 20% of triazolone, W-6001%, NNO 3%, 16015%, 1% of magnesium aluminum silicate, 0.2% of xanthan gum, 4% of ethylene glycol and the balance of deionized water (the balance is up to 100%) into a high-shear mixing kettle, shearing and mixing, and then sanding by using a sand mill to obtain the 25% of compound A.triazolone suspending agent with good dispersibility.
5. Preparation of suspoemulsion
Example 17.16% formulation of Compound A. Tebuconazole suspoemulsion
According to the formula requirement, adding 2% of compound A, 14% of tebuconazole, 1% of sodium dodecyl sulfate, D-4254%, 10% of dimethyl sulfoxide, 0203B 5%, 0.2% of xanthan gum, 4% of ethylene glycol, 3% of white carbon black and the balance of deionized water (the balance is up to 100%) into a mixing kettle, mixing and stirring by using a high shear machine, and then sanding in a sand mill to obtain the 16% compound A.tebuconazole suspoemulsion with good physical properties.
6. Preparation of dispersible oil suspending agent
EXAMPLE 18.20% Compound A. Tebuconazole dispersible oil suspension formulation
According to the formula requirement, adding 2% of compound A, 18% of tebuconazole, 36% of O, 808% of S, 804% of T, 1% of organic bentonite and the balance of methyl oleate (the balance is 100%) into a mixing kettle, stirring and mixing by using a high shear machine, and then sanding by using a sand mill to obtain the 20% of compound A.tebuconazole dispersible oil suspending agent with good dispersibility.
EXAMPLE 19.20% Compound A.Triazolol dispersible oil suspension formulation
According to the formula requirement, 5% of compound A, 15% of triadimenol, 36% of O-36%, 560EP 10%, 1% of organic bentonite and the balance of methyl oleate (the balance is 100%) are added into a mixing kettle, stirred and mixed by a high-shear machine, and then sanded by a sand mill, so that the 20% compound A-triadimenol dispersible oil suspending agent with good dispersibility can be obtained.
7. Preparation of wettable powder
EXAMPLE 20.10 preparation of wettable powder of Compound A. Tebuconazole
According to the formula requirement, adding 2% of compound A, 8% of tebuconazole, 5% of sodium lignosulphonate, D-4253%, 1% of sodium dodecyl sulfate, 3% of white carbon black and the balance of light calcium carbonate (supplementing to 100) into a mixer for mixing, and then crushing by a jet mill to obtain 10% of compound A-tebuconazole wettable powder with good physical properties.
EXAMPLE 21.20% preparation of Compound A. diniconazole wettable powder
According to the formula requirement, adding 10% of compound A, 10% of diniconazole, 3% of NNO, D-4253%, 1% of sodium dodecyl sulfate, 5% of white carbon black and the balance of kaolin (supplementing to 100) into a mixer for mixing, and then crushing by a jet mill to obtain 20% of compound A-diniconazole wettable powder with good physical properties.
EXAMPLE 22.30% preparation of wettable powder of Compound A.triazolone
According to the formula requirement, 10% of compound A, 20% of triazolone, 5% of sodium lignosulfonate, 3% of NNO, 1% of sodium dodecyl sulfate, 5% of white carbon black and the balance of diatomite (supplemented to 100%) are added into a mixer for mixing, and then crushed by a jet mill, so that 30% of compound A-triazolone wettable powder with good physical properties can be obtained.
8. Preparation of water dispersible granule
Example 23.50% preparation of Compound A Tebuconazole Water dispersible granules
According to the formula requirement, 10% of compound A, 40% of tebuconazole, 2% of EFW, 10% of sodium lignosulphonate, 5% of kaolin, 2% of carboxymethyl cellulose and ammonium sulfate are complemented to 100%. The raw materials are uniformly mixed, crushed by a jet mill to obtain mother powder, then a proper amount of water is added for mixing, and a squeezing type granulator is used for granulation, so that the 50% compound A.tebuconazole water dispersible granule with good physical property can be obtained.
Example 24.50% preparation of Compound A-triadimenol Water dispersible granules
According to the formula requirement, 5% of compound A, 45% of tebuconazole, 2% of EFW, 10% of sodium lignosulphonate, 20% of kaolin and ammonium sulfate are complemented to 100%. The raw materials are uniformly mixed, crushed by a jet mill to obtain mother powder, then a proper amount of water is added for mixing, and a squeezing type granulator is used for granulation, so that the 50% compound A-triadimenol water dispersible granule with good physical property can be obtained.
9. Preparation of dry suspending agent
EXAMPLE 25.70% preparation of Compound A.Tebuconazole Dry suspension
According to the formula requirement, 5% of compound A, 20% of tebuconazole, 8% of sodium lignosulfonate, 2% of kaolin and deionized water are complemented to 100% and added into a mixing kettle, a high shear machine is used for mixing and stirring, and then the mixture enters a sand mill for sand grinding. Thus obtaining the 25 percent of compound A.tebuconazole suspending agent with good dispersibility. Then spray granulation is carried out by using 25% of compound A.tebuconazole suspending agent, and 70% of compound A.tebuconazole dry suspending agent with good physical property can be obtained.
Preparation of control preparation samples
Example 26.20% formulation of Fluxapyroxad-pentoxazolone suspension
According to the formula requirement, 4% of fluxapyroxad, 16% of tebuconazole, W-6001%, 3% of NNO, 16015%, 1% of magnesium aluminum silicate, 0.2% of xanthan gum, 4% of ethylene glycol and the balance of deionized water (the balance is up to 100%) are added into a high-shear mixing kettle, and the mixture is sheared and mixed and then sanded by a sand mill, so that the 20% fluxapyroxad-tebuconazole suspending agent with good dispersibility can be obtained.
Indoor bioassay example
Determination of pathogenic bacteria of rice sheath blight
By adopting a toxic medium-containing method, 98% of compound A raw material medicine, 97% of tebuconazole raw material medicine and a mixed preparation of the test reagent are respectively 5, 2.5, 1.25, 0.625 and 0.3125mg/L in the concentration when the pathogenic bacteria of the rice sheath blight are tested; a blank control without drug was also set and repeated 3 times per treatment. Cooling the melted PDA culture medium to 60-70 deg.C, adding quantitative chemicals according to the above concentration to obtain toxic culture medium with different dosage, respectively inoculating the above pathogenic bacteria sheets with diameter of 0.5cm after cooling, and culturing in incubator (incubator conditions set at 25 + -1 deg.C). After 4d, investigation was conducted. And (4) measuring the growth diameter of each treated pathogenic bacteria colony to be tested respectively during investigation, and calculating the bacteriostasis rate.
The hypha bacteriostasis rate (%) (control colony diameter-treated colony diameter)/control colony diameter x 100 according to the bacteriostasis rate of different dosages of medicaments, using the medicament concentration logarithm value as an independent variable x, using the bacteriostasis rate probability value as a dependent variable y, and adopting DPS statistical software to calculate a toxicity regression equation, a correlation coefficient and EC50The value is obtained. According to EC50Values were calculated for combined virulence.
Combination evaluation of the Wadley method:
R＝EC50(theoretical value)/EC50(observed value)
Evaluation: if R does not deviate too much from 1, specifically between 0.5 and 1.5, the two compounds will have an additive effect after mixing; the R is more than or equal to 1.5, which shows that the synergistic effect is achieved; r is less than or equal to 0.5, and the expression has antagonism.
Theoretical reaction EC on mixtures containing two components50The theoretical value can be calculated according to the following equation:
Figure BDA0002461190860000111
a and B represent two components, respectively, and a + B is the ratio of the contents of the components in the mixture.
EC50(observed value) is the reaction actually observedAnd (4) data.
Table 1 shows the results of the indoor tests of the compound A technical product (TC), the tebuconazole technical product (TC) and the preparations containing two technical products with different proportions on pathogenic bacteria of rice sheath blight respectively
Reagent for testing Regression equation of virulence Correlation coefficient EC50(mg/L) R value
98% of Compound A TC Y＝5.3295+0.9105x 0.98 0.43 -
97% Tebuconazole TC Y＝4.3140+1.2226x 0.96 3.63 -
Example 1 (Compound A: Tebuconazole ═ 1:1) Y＝5.8435+1.4732x 0.97 0.26 3.07
Example 5 (Compound A: Tebuconazole ═ 1:2) Y＝5.6493+1.2708x 0.95 0.31 3.36
Example 9 (Compound A: Tebuconazole ═ 1:3) Y＝5.6812+1.3701x 0.95 0.32 3.96
Example 11 (Compound A: Tebuconazole ═ 1:4) Y＝5.5919+1.3592x 0.97 0.37 3.95
Example 13 (Compound A: Tebuconazole ═ 1:5) Y＝5.3929+1.5666x 0.97 0.56 2.89
Example 17 (Compound A: Tebuconazole ═ 1:7) Y＝4.4013+1.6210x 0.99 2.35 1.58
According to the visible examples, when the ratio of the compound A to the tebuconazole in the active ingredients in the examples is 1:1, 1:2, 1:3, 1:4, 1:5 and 1:7, R is more than or equal to 1.5, and the synergistic effect is realized.
Determination of Activity against Rice sheath blight disease
Examples of the test agent preparation comprising 99% of a compound a prodrug (TC), 95% of tebuconazole prodrug (TC), 96% of propiconazole prodrug (TC), 98% of difenoconazole prodrug (TC), 97% of epoxiconazole prodrug (TC), 97% of triazolone prodrug (TC), 93% of prothioconazole prodrug (TC), 95% of myclobutanil prodrug (TC), 98% of diniconazole prodrug (TC), 99% of penconazole prodrug (TC), 97% of triadimenol prodrug (TC), 98% of flutriafol (TC), a mixture of a compound a prodrug and Tebuconazole (TC), and a fungicide composition preparation containing a and triazoles as well as a self-made control preparation example 26 were 100, 25, 6.25, 1.56, 0.39mg/L in test concentrations, a control without adding a reagent was additionally provided, and 2 times of blank treatment were repeated. And (3) selecting rice potted seedlings which are uniform in growth and same in leaf age, carrying out stem and leaf spraying treatment by using a crop sprayer according to the concentration of the pesticide, placing the sprayed seedlings in a fume hood for airing, and inoculating rice sheath blight pathogenic bacteria after 24 hours. Inoculating by clamping and inoculating bacteria block method, wherein each pot is inoculated with 3 blocks of 0.25cm2The pathogenic bacteria block of rice sheath blight is arranged at the base of the rice seedling. After inoculation, the cells were cultured in a climatic greenhouse (temperature: 28 ℃ day., 25 ℃ night., relative humidity: 95%) under light, and then investigated after 7 days. During investigation, 6 leaf sheaths of the clamped bacterium blocks are investigated in each pot, the symptom degree is represented by 100-0 according to the harmful condition of the leaf sheaths and leaves of the rice, the 100 grade represents no disease, and the 0 grade represents the most serious disease degree. The test result shows that the preparation of the compound A and the triazole bactericidal composition has very excellent control effect on diseases, the biological activity of the mixed pot culture is obviously higher than that of a single control agent, and the mixed pot culture has obvious synergistic effect, and the results are detailed in the following tables 2 and 3.
TABLE 2 indoor screening of the activity of compound A and triazole fungicide active ingredients on rice sheath blight
Figure BDA0002461190860000121
TABLE 3 indoor screening of different dosage forms of the compound A + triazole fungicide composition for rice sheath blight disease activity
Figure BDA0002461190860000131
Determination of Activity against Soybean Rust
The test agent comprises 99% of compound A technical material (TC), 95% of tebuconazole technical material (TC), 96% of propiconazole technical material (TC), 98% of difenoconazole technical material (TC), 97% of epoxiconazole technical material (TC), 97% of triazolone technical material (TC), 93% of prothioconazole technical material (TC), 95% of myclobutanil technical material (TC), 98% of diniconazole technical material (TC), 99% of penconazole technical material (TC), 97% of triadimenol technical material (TC), 98% of flutriafol technical material, compound A technical material and tebuconazole technical material mixed (TC), and the test concentration of the compound A and triazole fungicide composition preparation in the test agent example 26 and the self-made control preparation example 26 are 6.25, 3.125, 1.56, 0.78 and 0.39 mg/L; selecting potted soybean seedlings with regular and consistent growth, cutting off growth points, reserving 2 true leaves, carrying out spraying treatment on a crop sprayer according to the set concentration of a test agent, additionally arranging a blank control without applying the agent, and repeating the treatment for 3 times. Spraying, and air drying in a ventilation kitchen. Inoculating soybean rust spore suspension (1 × 106/mL) after 24h, placing in an artificial climate chamber (temperature: 25 ℃ day, 20 ℃ night, relative humidity: 95%) after inoculation, culturing for 1d, then moving to a greenhouse for normal management, culturing for 10d under the conditions (temperature: 23-28 ℃ day, 18-20 ℃ night), and investigating the control effect, wherein the investigation result is represented by 100-0, and the 100 grade represents no disease and the 0 grade represents the most serious disease degree. The test results show that the preparation of the bactericidal composition containing the compound A and the triazole has very excellent control effect on diseases, the pot biological activity of the mixed preparation is obviously higher than that of a single control preparation, and the mixed preparation has obvious synergistic effect, and the results are detailed in the following tables 4 and 5.
TABLE 4 indoor screening of Soybean Rust Activity of Compound A and original triazole fungicides
Figure BDA0002461190860000141
TABLE 5 indoor screening of soybean rust activity of different formulations of Compound A and triazole fungicide compositions
Figure BDA0002461190860000142
Activity assay for corn rust
The test reagent comprises 99% of compound A technical material (TC), 95% of tebuconazole technical material (TC), 96% of propiconazole technical material (TC), 98% of difenoconazole technical material (TC), 97% of epoxiconazole technical material (TC), 97% of triazolone technical material (TC), 93% of prothioconazole technical material (TC), 95% of myclobutanil technical material (TC), 98% of diniconazole technical material (TC), 99% of penconazole technical material (TC), 97% of triadimenol technical material (TC), 98% of flutriafol technical material (TC), test concentration of compound A technical material and tebuconazole technical material mixed (TC) and composition preparation containing compound A and triazole fungicide, and self-made control preparation examples 26 are 6.25, 3.125, 1.56, 0.78 and 0.39 mg/L; selecting potted trefoil stage corn seedlings which grow regularly and uniformly, carrying out spray treatment on the potted trefoil stage corn seedlings according to the concentration set above on a crop sprayer, inoculating a corn rust germ spore suspension (5 multiplied by 106/mL) after 24 hours, and spraying the corn rust germ spore suspension on host crops. Placing in a phytotron (temperature: 25 deg.C in the day, 20 deg.C in the night, relative humidity: 95%) after inoculation, culturing for 1d, then moving the plants to a greenhouse for normal management, investigating the prevention and treatment effect of the compound after 7d, and calculating the prevention and treatment effect by disease index. The survey results are expressed as 100-0, with "100" representing no disease and "0" representing the most severe degree of disease. The test result shows that the preparation of the compound A and the triazole bactericidal composition has very excellent control effect on diseases, the biological activity of the mixed pot culture is obviously higher than that of a single control agent, and the mixed pot culture has obvious synergistic effect, and the results are detailed in the following tables 6 and 7.
TABLE 6 indoor screening of different formulations of Compound A + Tebuconazole for corn rust activity
Figure BDA0002461190860000151
TABLE 7 indoor screening of corn rust activity by different formulations of Compound A + Tebuconazole
Figure BDA0002461190860000161
From the data, the agriculturally applicable various formulations prepared by the compound A and the triazole fungicide composition have the control range of crops far beyond rice sheath blight disease, soybean rust disease and corn rust disease mentioned in the examples, and have positive control effects on other plant diseases caused by ascomycotina, basidiomycotina and deuteromycotina. Those not described in detail in this specification are within the skill of the art.

Claims (7)

1. A germicidal composition formulation, characterized by: the active components of the sterilization composition preparation comprise a compound A and a triazole bactericide, and the mass ratio of the two active components is 1:50-50: 1; the triazole bactericide is selected from: one or more of tebuconazole, propiconazole, difenoconazole, epoxiconazole, triadimefon, prothioconazole, flusilazole, diniconazole, myclobutanil, diniconazole, penconazole, hexaconazole, triadimenol, cyproconazole, fluquinconazole, flutriafol, metconazole, imibenconazole, ipconazole, triticonazole, bitertanol, epoxiconazole, tetraconazole, imazalil, tetraconazole, simeconazole or triflumizole; the structural formula of the compound A is shown as follows,
Figure FDA0002461190850000011
in the formula, R1Selected from hydrogen or methyl; r2Selected from methyl, ethyl, propyl or isopropyl.
2. The fungicide formulation according to claim 1, wherein: the triazole fungicide is selected from tebuconazole, propiconazole, difenoconazole, epoxiconazole, triadimefon, prothioconazole, flusilazole, myclobutanil, diniconazole, penconazole, triadimenol, cyproconazole, flutriafol, imibenconazole, triticonazole or tetraconazole.
3. The fungicide formulation according to claim 1, wherein: the mass ratio of the compound A in the active component to the triazolone, the diniconazole, the triadimenol, the cyproconazole or the flutriafol in the triazole fungicide is 1:25-25: 1; the mass ratio of the compound A in the active ingredients to tebuconazole, propiconazole, difenoconazole, epoxiconazole, imibenconazole or triticonazole in the triazole fungicide is 1:20-20: 1; the mass ratio of the compound A in the active component to prothioconazole, flusilazole, myclobutanil, penconazole or tetraconazole in the triazole fungicide is 1:10-10: 1.
4. A fungicide formulation according to any one of claims 1 to 3, characterized in that: the compound A has a structural formula as follows: r1 is selected from methyl; r2 is selected from propyl.
5. The fungicide formulation according to claim 4, wherein: the dosage forms of the bactericide preparation are missible oil, aqueous emulsion, microemulsion, suspending agent, suspoemulsion, dispersible oil suspending agent, wettable powder, water dispersible granule and dry suspending agent.
6. The fungicide formulation according to claim 5, wherein: the preparation comprises an active ingredient, at least one auxiliary agent and at least one carrier; wherein the active ingredients in the preparation account for 10-80% of the mass of the preparation.
7. Use of a bactericidal formulation according to claim 1 wherein: the bactericidal preparation is used as a bactericide for plant diseases caused by ascomycotina, basidiomycotina and deuteromycotina.
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CN109805018A (en) * 2017-11-21 2019-05-28 沈阳中化农药化工研发有限公司 A kind of Fungicidal composition and application
CN109805019A (en) * 2017-11-21 2019-05-28 沈阳中化农药化工研发有限公司 Fungicidal composition and its application
CN109805017A (en) * 2017-11-21 2019-05-28 沈阳中化农药化工研发有限公司 A kind of Fungicidal composition and its application

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CN104649973A (en) * 2013-11-25 2015-05-27 中国中化股份有限公司 Pyrazole amide compound and application thereof
CN109418268A (en) * 2017-08-29 2019-03-05 沈阳中化农药化工研发有限公司 A kind of biocide preparation and its application
CN109805018A (en) * 2017-11-21 2019-05-28 沈阳中化农药化工研发有限公司 A kind of Fungicidal composition and application
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