WO2019090817A1 - Composition herbicide contenant le benzène-azole fluoridone et ses applications - Google Patents

Composition herbicide contenant le benzène-azole fluoridone et ses applications Download PDF

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Publication number
WO2019090817A1
WO2019090817A1 PCT/CN2017/112019 CN2017112019W WO2019090817A1 WO 2019090817 A1 WO2019090817 A1 WO 2019090817A1 CN 2017112019 W CN2017112019 W CN 2017112019W WO 2019090817 A1 WO2019090817 A1 WO 2019090817A1
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WIPO (PCT)
Prior art keywords
oxazolone
polyoxyethylene ether
acid
herbicidal composition
accession number
Prior art date
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PCT/CN2017/112019
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English (en)
Chinese (zh)
Inventor
彭学岗
赵德
刘娜
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青岛清原化合物有限公司
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Application filed by 青岛清原化合物有限公司 filed Critical 青岛清原化合物有限公司
Priority to MX2020004852A priority Critical patent/MX2020004852A/es
Publication of WO2019090817A1 publication Critical patent/WO2019090817A1/fr

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    • A—HUMAN NECESSITIES
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    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
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    • A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
    • A01N33/18—Nitro compounds
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    • A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34
    • A01N57/04—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34 containing acyclic or cycloaliphatic radicals
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
    • A01N57/14—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing aromatic radicals
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals

Definitions

  • the invention belongs to the field of pesticides, and in particular relates to a herbicidal composition containing oxazolone and its application.
  • Chemical weeding is the most economical and effective means of controlling weeds in farmland.
  • long-term continuous high-dose use of single-species or single-acting chemical herbicides is prone to problems such as weed resistance and resistance evolution.
  • oxazolone is a newly developed HPPD inhibitor herbicide for post-emergence stem and leaf treatment of corn field. It has excellent biological activity and can effectively control a variety of malignant weeds in corn fields.
  • Rational compounding or compounding of herbicide compounds has the advantages of expanding weed spectrum, improving control effect, delaying the occurrence and development of weed resistance and drug resistance, and is one of the most effective methods to solve the above problems. Therefore, the production of cockroaches requires the development of a variety of herbicidal compositions that have high safety, broad spectrum of herbicides, can produce synergistic effects and solve the problem of resistant weeds.
  • the present invention provides a herbicidal composition containing oxazolone and an application thereof.
  • the composition can effectively prevent weed problems such as wormwood and cattle larvae in crop fields, and has the characteristics of expanding herbicidal spectrum, reducing application amount, safety to crops, synergistic effect and solving resistant weeds.
  • a herbicidal composition containing oxazolone comprising a herbicidally effective amount of active ingredient A and active ingredient B, wherein active ingredient A is oxazolone, and active ingredient B may be selected from one of the following compounds or Multiple:
  • VLCFA inhibitors pretilachlor (CAS accession number: 51218-49-6), thiacillin (CAS accession number: 73250-68-7), sulfonepyrazol (CAS accession number: 447399- 55-5), samarium phosphate (CAS accession number: 64249-01-0), xylenolamine (CAS accession number: 87674-68-8), tetrazoyl oxalate (CAS accession number: 158237-07 -1), triazolamide (CAS accession number: 212201-70-2), oxadiachlor (CAS accession number: 125306-83-4), piperacine (CAS accession number: 24151-93-7) , pyrazolamide (CAS accession number: 67129-08-2), chlorfenapyr (CAS accession number: 1918-16-7), acetochlor (CAS accession number: 106700-29-2);
  • PPO inhibitors flufenacil (CAS accession number: 72178-02-0), oxaloin (CAS accession number: 19666-30-9), Propyne oxaloxone (CAS accession number: 39807-15-3), oxazolidine (CAS accession number: 158353-15-2), propiflufenic acid (CAS accession number: 103361-09-7), Cyclopentyl ketone (CAS accession number: 110956-75-7), tiafenacil (CAS accession number: 1220411-29-9), pyriprose (CAS accession number: 129630-19-9);
  • PSII inhibitors Xicaojing (CAS accession number: 1014-70-6), Tedingjing (CAS accession number: 886-50-0), isopropyl net (CAS accession number: 4147-51-7 ), harm grass net (CAS accession number: 845-52-3), diquat grass net (CAS accession number: 1014-69-3), oxazinone (CAS accession number: 64529-56-2), benzoazine Oxalone (CAS accession number: 41394-05-2), cyanazine (CAS accession number: 21725-46-2), fluroxypyr (CAS accession number: 2164-17-2), butylthiazol (CAS accession number: 34014) -18-1), Sha Plong (CAS registration number: 42609-52-9), Lv Gulong (CAS registration number: 1746-81-2), Bromo Valley (CAS registration number: 3060-89-7) , Cao Bulong (CAS accession number: 555-37-3), pyridazinol (CAS accession number:
  • ALS inhibitors pyrazosulfuron (CAS accession number: 93697-74-6), thioxasulfuron (CAS accession number: 317815-83-1), azoxysulfuron (CAS accession number: 570415 -88-2), oxazinsulfuron-methyl (CAS accession number: 868680-84-6), ethoxysulfuron (CAS accession number: 126801-58-9), cumene sulfonate (CAS accession number: 213464- 77-8), fluoxetine (CAS accession number: 96525-23-4), penoxsulam (CAS accession number: 219714-96-2), chlorosulfonamide (CAS accession number: 147150 -35-4)), imazamox (CAS accession number: 114311-32-9), methimazole nicotinic acid (CAS accession number: 104098-48-8), imidazolium nicotinic acid (CAS accession number: 81385-77
  • Microtubule assembly inhibitors trifluralin (CAS accession number: 1582-09-8), zhongdingling (CAS accession number: 33629-47-9), pendimethalin (CAS accession number: 40487- 42-1), Diltiazem (CAS accession number: 33629-47-9), flurazepam (CAS accession number: 97886-45-8), ethylenebutene fluoride (CAS accession number: 55283-68- 6), amisulpole (CAS accession number: 19044-88-3), fluramide (CAS accession number: 1861-40-1), thiabidine (CAS accession number: 117718-60-2), take Cao Te (CAS accession number: 23950-58-5), diquat (CAS accession number: 1861-32-1), and oxaloplatin (CAS accession number: 36335-67-8);
  • HPPD inhibitors sulcotrione (CAS accession number: 99105-77-8), mesotrione (CAS accession number: 104206-82-8), oxafluridone (CAS accession number: 210631-68 -8), cyclohexanone (CAS accession number: 335104-84-2), flufenicone (CAS accession number: 352010-68-5), furansulfoxone (CAS accession number: 473278-76-1) , bicyclosulfonone (CAS accession number: 156963-66-5), lancotrione (CAS accession number: 1486617-21-3), sulfonylpyrazole (CAS accession number: 365400-11-9), pyrazol (CAS Accession number: 58011-68-0), oxalofen (CAS accession number: 82692-44-2), tolpyralate (CAS accession number: 1101132-67-5), fenquinotrione (CAS accession number: 1342891-70-6)
  • PDS inhibitors flurochlorone (CAS accession number: 61213-25-0), furoserone (CAS accession number: 96525-23-4), flufenyl oxalate (CAS accession number: 113614- 08-7), fluroxypyr (CAS accession number: 27314-13-2), fluroxylin (CAS accession number: 59756-60-4);
  • Lipid synthesis (non-acetyl-CoA carboxylase) inhibitors benzathine (CAS accession number: 52888-80-9), grass herbicide (CAS accession number: 2212-67-1), grass Dan (CAS registration number: 28249-77-6), furose yellow (CAS accession number: 68505-69-1), ethoxyfurant yellow (CAS accession number: 26225-79-6), wild wheat (CAS login No.: 2303-17-5), chlorpyrifos (CAS accession number: 28249-77-6), chlorpyrifos (CAS accession number: 1929-77-7), butyl grass (CAS accession number: 2008-41 -5), ring grass enemy (CAS accession number: 1134-23-2), piperidan (CAS accession number: 61432-55-1), pento-dan (CAS accession number: 85785-20-2);
  • EPSPS inhibitors oxalate (CAS accession number: 81591-81-3);
  • GS inhibitors bialaphos (CAS accession number: 35597-43-4), glufosinate (CAS accession number: 35597-44-5);
  • PSI inhibitors paraquat (CAS accession number: 1910-42-5);
  • DHP inhibitors sulforaphane (CAS accession number: 3337-71-1);
  • the weight ratio of A and B is 1:200-200:1, preferably 1:150-150:1, more preferably 1:120-120:1; further, the weight ratio of A and B is 1:100- 100:1, preferably 1:80-80:1, more preferably 1:50-50:1; further, the weight ratio of A and B is 1:30-30:1, preferably 1:10-10:1 More preferably 1:5-5:1.
  • the mass percentage of A and B in the herbicidal composition is from 1 to 95%, preferably from 10 to 80%, based on the total amount.
  • the herbicidal composition further comprises a conventional auxiliary agent comprising a carrier and a surfactant.
  • carrier refers to an organic or inorganic, natural or synthetic material. They aid in the administration of the active ingredient which is generally inert and must be agriculturally acceptable, especially accepted by the treated plant.
  • the carrier may be solid, such as clay, natural or synthetic silicates, silica, resins, waxes, solid fertilizers, etc.; or liquid, such as water, alcohols, ketones, petroleum fractions, aromatic or waxy hydrocarbons, chlorine Hydrocarbons, liquefied gases, etc.
  • Surfactants may include emulsifiers, dispersants or wetting agents, which may be ionic or nonionic. Examples which may be mentioned are salts of polyacrylic acid, lignosulfonates, salts of phenolsulfonic or naphthalenesulfonic acid, ethylene oxide with aliphatic alcohols or with aliphatic acids or with aliphatic amines and substituted phenols (especially a polymer of an alkylphenol or an arylphenol, a sulfosuccinate, a taurine derivative (especially a taurine alkyl ester), a phosphate ester of an alcohol or a phosphate of a polyhydroxyethylated phenol, Alkyl sulfonates, alkyl aryl sulfonates, alkyl sulfates, lauryl ether sulfates, fatty alcohol sulfates, and sulfated hexadecane, hepta-
  • compositions may also contain various other components such as protective colloids, binders, thickeners, thixotropic agents, penetrants, stabilizers, chelating agents, dyes, colorants, and polymers.
  • compositions of the present invention may be diluted or used directly by the user prior to use.
  • the preparation can be prepared by a usual processing method, that is, after mixing the active material with a liquid solvent or a solid carrier, and then adding one or more of a surfactant such as a dispersing agent, a stabilizer, a wetting agent, a binder, an antifoaming agent, and the like.
  • a surfactant such as a dispersing agent, a stabilizer, a wetting agent, a binder, an antifoaming agent, and the like.
  • Specific formulations of the herbicidal compositions are dispersible oil suspending agents, aqueous suspensions, suspoemulsions, wettable powders, emulsifiable concentrates, water-dispersible granules (dry suspensions), aqueous emulsions, microemulsions.
  • compositions of the present invention can be combined with solid and liquid additives conventionally used in prior art formulations.
  • composition of Compound A and valerate and the combination of Compound A and cyclopyrimorate may be mixed with the following active substances, for example, "World Pesticide New Variety Technology Encyclopedia", China Agricultural Science and Technology Press, 2010.9 and the literature cited herein. Known substances.
  • the herbicide active substance mentioned below (remark: the name of the compound, or the common name according to the International Organization for Standardization (ISO), or the chemical name, when appropriate, the code name): acetochlor, butachlor, Alachlor, propisochlor, metolachlor, dimethoprim, pretilachlor, chlorfenapyr, acetochlor, naproxil, R-L-naproxil, enemies ,benzilin, dibenzoylamine, flufenacetamide, herbicide, flufenic acid, bromobutyramide, dimethoprim, high-performance metolachlor, ethoxy Bentochlor, flufenacet, methoxymethafen, metazachlor, isoxacillin, high-efficiency wheat straw methyl ester, high-efficiency wheat valproate, dipropenamide, acetochlor, butyrylamine, Cyclosporine, flufenacetamide, heptylacetamide, isobutach
  • the herbicidal composition further comprises a safener selected from the group consisting of dibenzoxazole acid (CAS accession number: 163520-33-0), cyprosulfamide (CAS accession number: 221667-31-8), pyrazolium ester (CAS) Accession number: 135590-91-9), detoxification quinine (CAS accession number: 99607-70-2), gibberellic acid (CAS accession number: 77-06-5), furilazole (CAS accession number: 121776- 33-8), one or more of metcamifen (CAS accession number: 129531-12-0).
  • a safener selected from the group consisting of dibenzoxazole acid (CAS accession number: 163520-33-0), cyprosulfamide (CAS accession number: 221667-31-8), pyrazolium ester (CAS) Accession number: 135590-91-9), detoxification quinine (CAS accession number: 99607-70-2), gibberellic acid (CAS accession number
  • composition of the present invention can be applied to the leaves of the plants to be treated by spraying, i.e., to the weeds, particularly on the surface which is infested or susceptible to weeds which are harmful to the growth of the crop.
  • composition of the present invention is environmentally friendly and is easily degraded in the environment, and is suitable for use in various crop fields.
  • the herbicidal composition of the invention has low cost and convenient use, and has great economic and social benefits for its popularization and application.
  • suspoemulsion processing equipment mixing tank, colloid mill, sand mill, shearing machine, and the like.
  • the water phase material is put into the mixing kettle, stirred and mixed, then passed through the colloid mill, then enters the sand mill three-stage sanding, and finally sheared uniformly in the shearing machine, and the test is transferred and ready for use;
  • the oil phase material is put into the mixing tank, the solvent oil and the emulsifier are added, and the mixture is stirred and dissolved uniformly; then the aqueous phase material is added into the shearing kettle, and the oil phase material is slowly drawn into the shearing kettle under shearing condition. Cut while feeding, continue to cut evenly, after passing the test, transfer to the tank filling.
  • the above water suspension processing equipment mixing tank, colloid mill, sand mill, shearing machine and the like.
  • the above dispersible oil suspension processing equipment mixing tank, colloid mill, sand mill, shearing machine and the like.
  • the above dispersible oil suspension agent processing process all materials are put into the mixing kettle, stirred and mixed, then passed through the colloid mill, then enter the sand mill three-stage sanding, and finally cut evenly in the shearing machine, after passing the test, transfer To the tank filling.
  • the above water dispersible granule processing equipment a jet mill, a coulter mixer, a basket granulator, a drying box, a screening machine, and the like.
  • the above water-dispersible granule processing process the above materials are uniformly mixed and pulverized by air flow, added with water to knead and granulate, then dried, and finally sieved to obtain a finished product.
  • Niu Fanyu was collected from Xinghua, Jiangsu province, and the seedlings were collected from Tai'an, Shandong.
  • the above weeds were cultured by pot culture, and placed in an enamel pan with 180 ⁇ 140mm plastic nutrient bowl.
  • the surface soil was collected from the farmland and passed through the air-screened surface (4/5).
  • the initial humidity of the soil was controlled at 20%.
  • the seeds with full and uniform grain are soaked in warm water at 25 °C for 6 hours, germinated in a 28 °C biochemical incubator (dark), and the newly weed seeds are evenly placed on the soil surface, and then the soil is covered according to the seed size. -1cm.
  • the required active ingredient B is purchased from a reagent company, and A is produced by the company.
  • the original drug was treated with acetone as a solvent, diluted with 0.1% emulsifier Tween-80 aqueous solution, and now diluted.
  • a and B In determining the ratio or content of A and active ingredient B, it should be measured from the characteristics and virulence of the two agents, and the main purpose of the formulation should be considered. Based on the preliminary pre-test, the A and B active ingredients were used alone and mixed. See the table for the quantities. Water containing no drug, the same solvent and an emulsifier was used as a blank control.
  • Each treatment was repeated 4 times, and each time 3 pots were treated, 20 seeds of weed seeds were planted per pot, and 60 plants per treatment.
  • the cultured test materials were evenly placed on a platform with an area of 0.5 m 2 , and sprayed with a 3WP-2000 type walking spray tower, and the spray amount was 30 kg/ha.
  • the spray pressure was 0.3 MPa. After all the liquid medicines have been sprayed, close the air valve. After 30 seconds, open the spray tower door and take out the nutrient bowl. Then open the gas valve, spray 50 mL of water, and clean the spray tube.
  • weed culture see 1.1, refer to the "Pesticide Indoor Bioassay Test Guidelines Herbicide”. See 2.3.2 for the method of administration, using stem and leaf treatment. After the treatment, it was transferred to a greenhouse for routine culture, and a water layer of 1-2 cm was always maintained during the test.
  • the whole seedlings of the living weeds were cut along the surface of the soil with a blade, and the fresh weight of the weeds was weighed by an analytical balance. For dead weeds, the fresh weight is zero.
  • the investigation was conducted 20 days after the treatment, and a total of 1 investigation was conducted.
  • E measured inhibition rate
  • the E-E0 value is greater than 10% for synergism, less than -10% for antagonism, and between -10% and 10% for additive effect. According to the actual control effect and the characteristics of the herbicide, the balance of the formula and other factors determine the best ratio.
  • X is the fresh weight inhibition rate when the amount of the active ingredient A is P; and Y is the fresh weight inhibition rate when the amount of the active ingredient B is Q.
  • Niu Fanyu was collected from Xinghua, Jiangsu province, and the seedlings were collected from Tai'an, Shandong.
  • the test soil was dosed to 3/4 of the pots and then watered from the bottom of the pots to completely wet the soil to saturation.
  • the pretreated weed seeds were uniformly distributed on the surface, and the soil was covered by 0.5-2 cm according to the seed size, and was used 24 hours after sowing.
  • GA10 type one ten thousand electronic balance Germany
  • ZDR2000 intelligent data recorder Hagzhou Zeda Instrument Co., Ltd.
  • SPX type intelligent biochemical incubator Naingbo Jiangnan Instrument Factory
  • the required active ingredient B is a commercially available original drug, and A is produced by the company.
  • the original drugs were all treated with acetone as a solvent, diluted with 0.1% emulsifier T-80 aqueous solution, and now diluted.
  • each group of A and active ingredient B When determining the distribution ratio or content of each group of A and active ingredient B, it should be measured from the characteristics and virulence of the two agents, and the main purpose of the formulation should be considered. On the basis of the preliminary pre-test, the A and B active ingredients used alone and mixed dosages are shown in the table. Water containing no drug, the same solvent and an emulsifier was used as a blank control.
  • Each treatment was repeated 4 times, 3 pots per treatment, and 30 seeds of weed seeds were seeded per pot.
  • Table 20A The actual control effect and combined effect evaluation of the mixed with the pyriprene ether on the seedlings (stem and leaf treatment)
  • the herbicidal composition prepared in Examples 1) to 126) was subjected to a field weed effect test.
  • the weeds that occur in the field mainly include: sage, leeks, burdock, Indian leeks and so on.
  • Soil treatment Before the weeds are germinated, hand sprayer, water volume 45 kg / 667 m 2 , evenly sprayed on the soil surface.
  • Stem and leaf treatment When the weeds are in the 3-4 leaf stage, hand sprayer, water volume 30 kg / 667 m 2 , spray evenly with stem and leaf spray.
  • test agents and dosages are shown in Table 127.
  • the plot area is 50 square meters, and each treatment is repeated 4 times. See Table 127 for investigation of the control effect 45 days after application.
  • the composition is useful for controlling weeds such as sage, amaranth, burdock, and leeks, and has surprising and unexpected synergistic effects.
  • the synergistic effect is more significant at low doses, which can reduce the dosage and reduce the pollution to the environment, and the reasonable compounding reduces the agricultural cost, and is effective for the resistance of ALS and ACCase inhibitors, and has a good application. prospect.

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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)
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  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention concerne le domaine des pesticides et se rapporte en particulier à une composition herbicide contenant le benzène-azole fluridone et ses applications. La composition herbicide comprend une quantité efficace du point de vue herbicide de l'ingrédient actif A et de l'ingrédient actif B : A est le benzène-azole fluridone ; et B peut être un ou plusieurs composés choisis parmi les suivants : des inhibiteurs de VLCFA, de PPO, de PSII, d'ALS, de l'assemblage de microtubules, de HPPD, de PDS, de la synthèse des lipides, d'EPSPS, de GS, de PSI, de DHP, des hormones de synthèse et similaires. La composition permet d'empêcher efficacement l'apparition de mauvaises herbes, et d'éliminer efficacement celles-ci, telles que la sagesse-des-chirurgiens, Malachium aquaticum, etc. dans des champs de culture ; elle est sans danger pour les cultures et permet d'étendre le spectre herbicide, de réduire la quantité appliquée, de produire une synergie et de résoudre le problème des mauvaises herbes résistantes aux herbicides.
PCT/CN2017/112019 2017-11-09 2017-11-21 Composition herbicide contenant le benzène-azole fluoridone et ses applications WO2019090817A1 (fr)

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CN106577715A (zh) * 2016-11-01 2017-04-26 广东中迅农科股份有限公司 含有苯唑氟草酮和烟嘧磺隆以及氯氟吡氧乙酸的农药组合物
CN106966983A (zh) * 2017-05-02 2017-07-21 青岛清原化合物有限公司 无定形态苯唑氟草酮及其制备方法和用途
CN107311930A (zh) * 2017-07-13 2017-11-03 青岛清原化合物有限公司 双唑草酮b晶型及其制备方法和用途

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CN114586797A (zh) * 2020-12-03 2022-06-07 青岛清原抗性杂草防治有限公司 包含灭草松和砜嘧磺隆的三元除草组合物及其应用
CN114586797B (zh) * 2020-12-03 2023-09-01 青岛清原作物科学有限公司 包含灭草松和砜嘧磺隆的三元除草组合物及其应用

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