WO2020241788A1 - Composition liquide comprenant du mefentrifluconazole - Google Patents

Composition liquide comprenant du mefentrifluconazole Download PDF

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Publication number
WO2020241788A1
WO2020241788A1 PCT/JP2020/021216 JP2020021216W WO2020241788A1 WO 2020241788 A1 WO2020241788 A1 WO 2020241788A1 JP 2020021216 W JP2020021216 W JP 2020021216W WO 2020241788 A1 WO2020241788 A1 WO 2020241788A1
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WO
WIPO (PCT)
Prior art keywords
mefentrifluconazole
composition
oil
present
diseases
Prior art date
Application number
PCT/JP2020/021216
Other languages
English (en)
Inventor
Atsushi Watanabe
Yoshinao Sada
Original Assignee
Sumitomo Chemical Company, Limited
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sumitomo Chemical Company, Limited filed Critical Sumitomo Chemical Company, Limited
Priority to AU2020283106A priority Critical patent/AU2020283106A1/en
Priority to US17/614,921 priority patent/US20220248674A1/en
Priority to BR112021024061A priority patent/BR112021024061A2/pt
Priority to CA3142280A priority patent/CA3142280A1/fr
Publication of WO2020241788A1 publication Critical patent/WO2020241788A1/fr

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Classifications

    • 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

Definitions

  • the present invention relates to a liquid composition for controlling plant diseases, which comprises mefentrifluconazole.
  • mefentrifluconazole is known as an active ingredient for a plant disease control agent (for example, refer to US2014/0155262A1 and WO2017/102905A1).
  • Patent Document 1 US2014/0155262A1
  • Patent Document 2 WO2017/102905A1
  • An object of the present invention is to provide a composition which is excellent in plant disease control effect.
  • a liquid composition comprising mefentrifluconazole, an oil adjuvant, and water and having a concentration of the oil adjuvant within a specific range shows a synergistic effect and is excellent in plant disease control effect. More specifically, the present invention is as described below.
  • a liquid composition comprising an effective amount of mefentrifluconazole, 0.1 to 10% by volume of an oil adjuvant, and water.
  • the oil adjuvant is Crop Oil Concentrates (COC), Methylated Seed Oils (MSO), or High Surfactant Oil Concentrates (HSOC).
  • [3] The liquid composition according to [1] or [2], wherein a concentration of mefentrifluconazole is 2000 to 10000 ppm.
  • [4] The liquid composition according to any one of [1] to [3], wherein the concentration of the oil adjuvant is 1.25 to 10 % by volume.
  • [5] A method for controlling plant diseases, comprising the steps of mixing a mefentrifluconazole-containing formulation, an oil adjuvant, and water to prepare a liquid composition comprising an effective amount of mefentrifluconazole, 0.1 to 10% by volume of an oil adjuvant, and water; and applying the liquid composition to a plant or soil for cultivating the plant.
  • Plant diseases can be controlled according to the present invention.
  • the liquid composition according to the present invention (hereinafter referred to as the composition of the present invention) comprises an effective amount of mefentrifluconazole.
  • Mefentrifluconazole is a known compound and described, for example, in US Patent Application Publication No. 2014/0155262A1 and WO2017/102905A1. Mefentrifluconazole can be synthesized by the method as described in US Patent Application Publication No. 2014/0155262A1 and WO2017/102905A1.
  • the concentration of mefentrifluconazole in the composition of the present invention is usually 100 to 10000 ppm, preferably 500 to 8000 ppm, more preferably 1000 to 7000 ppm, and most preferably 2000 to 6000 ppm.
  • Specific concentrations of mefentrifluconazole includes 150 ppm, 300 ppm, 500 ppm, 800 ppm, 1500 ppm, 3000 ppm, 5000 ppm, and 8000 ppm.
  • composition of the present invention can include mefentrifluconazole in the solid state. That is, the composition of the present invention can be an aqueous suspension which includes mefentrifluconazole in the solid state, oil adjuvant, and water.
  • the composition of the present invention comprises an oil adjuvant.
  • Adjuvants are generally known as substances to be added to enhance the action of pesticides or to modify the physical properties of mixtures for spraying (spray liquid).
  • the oil adjuvant refers to oil-containing adjuvants, which contain a surfactant to emulsify oil when they are mixed with water. Oil adjuvants are classified according to the type of oil, the type of surfactant, and contents thereof. Examples of oils contained in oil adjuvants include mineral oils and vegetable oils. Mineral oils are oils of minerals such as petroleum, and contain a mixture of hydrocarbons.
  • hydrocarbons examples include paraffinic hydrocarbons, naphthenic hydrocarbons, aromatic hydrocarbons, other unsaturated hydrocarbons and combinations thereof.
  • Vegetable oils are oils extracted from seeds, and examples of the seeds include seeds of corn, cotton, peanut, rapeseed, sunflower, canola and soybean.
  • the vegetable oil may be a vegetable oil that has been modified such as methylation.
  • oil adjuvants include COC, HSOC, and MSO.
  • COC Crop Oil Concentrates
  • COC Crop Oil Concentrates
  • HSOC High Surfactant Oil Concentrates
  • HSOC oil adjuvants containing an oil and a surfactant, wherein the total content of the oil is at least 50% by weight and the total content of the surfactant is 25 to 50% by weight.
  • MSO Methylated Seed Oils
  • COC examples include Agri-Dex (manufactured by Helena), Crop Oil Concentrate (manufactured by Helena), Herbimax (manufactured by Loveland), Ortech (manufactured by Rosens), Premium Crop Oil (manufactured by United Suppliers), Premium COC (manufactured by West Central), Prime Oil (manufactured by Winfield), Protyx Aerial (manufactured by Precision Laboratories), and ROC Crop Oil (manufactured by Wilbur-Ellis).
  • Examples of commercially available HSOC include Between (manufactured by United Suppliers), Destiny (manufactured by Winfield), Diplomat (manufactured by Rosens), Exchange (manufactured by Precision Laboratories), Hi-Load (manufactured by Simplot), High Load (manufactured by Wilbur-Ellis), Kixyt (manufactured by Precision Laboratories), Savvy (manufactured by West Central), Stake (manufactured by West Central), and Superb HC (manufactured by Winfield).
  • MSO examples include Adigor (manufactured by Syngenta), MSO Leci-Tech (manufactured by Loveland), MSO Ultra (manufactured by Precision Laboratories), Persist Ultra (manufactured by J. R. Simplot), Premium MSO (manufactured by Helena), Soy-Stik (manufactured by West Central), Succeed (manufactured by United Suppliers), Sundance II (manufactured by Rosens), Superspread MSO (manufactured by Wilbur-Ellis), and Upland MSO (manufactured by West Central).
  • the composition of the present invention usually comprises 0.1 to 10% by volume, preferably 0.2 to 10% by volume, 1 to 10% by volume or 1 to 7% by volume of an oil adjuvant.
  • the oil adjuvant is COC
  • the concentration of COC in the composition of the present invention is usually 0.2 to 10% by volume, preferably 0.4 to 10% by volume, 2 to 10% by volume, 2 to 7% by volume or 2 to 6% by volume.
  • the oil adjuvant is HSOC
  • the concentration of HSOC in the composition of the present invention is usually 0.1 to 5% by volume, preferably 0.2 to 5% by volume, 1 to 5% by volume or 1 to 3.5% by volume.
  • the concentration of MSO in the composition of the present invention is 0.1 to 10% by volume, preferably 1 to 10% by volume or 1 to 7% by volume. Specific percentages by volume of an oil adjuvant includes 0.15%, 0.3%, 0.5%, 0.75%, 1.25%, 1.5%, 3%, 6%, and 8%. Further, the weight ratio of mefentrifluconazole to the oil adjuvant in the composition of the present invention is preferably in the range of 1 : 0.1 to 1 : 650 or 1 : 10 to 1 : 160.
  • the weight ratio of mefentrifluconazole to COC in the composition of the present invention is preferably in the range of 1 : 0.2 to 1 : 650, 1 : 0.2 to 1 : 160 or 1 : 2 to 1 : 100.
  • the weight ratio of mefentrifluconazole to HSOC in the composition of the present invention is preferably in the range of 1 : 0.1 to 1 : 300, 1 : 0.1 to 1 : 100 or 1 : 1 to 1 : 60.
  • the weight ratio of mefentrifluconazole to MSO in the present composition is preferably in the range of 1 : 0.1 to 650, or 1 : 10 to 1 : 160.
  • the composition of the present invention comprises water.
  • water water generally used to prepare a mixture for spraying in ordinary pesticide spraying is used.
  • the composition of the present invention is prepared by mixing a mefentrifluconazole-containing formulation, an oil adjuvant, and water.
  • the formulation type of the mefentrifluconazole-containing formulation may be any formulation type as long as the formulation is generally mixed with water to prepare a mixture for spraying (spray liquid) so that the mixture is sprayed.
  • examples of such formulation types include emulsifiable concentrates, wettable powders, water dispersible granules, and SC (suspension concentrates), and SC are preferred.
  • the mefentrifluconazole-containing formulation can be prepared by methods known per se for the preparation of pesticide formulations, for example by mixing mefentrifluconazole, inert carriers, and surfactants, and, optionally further other auxiliary agents for formulation.
  • Examples of the inert carriers used in the preparation of the mefentrifluconazole-containing formulation include solid carriers and liquid carriers.
  • Examples of solid carriers include mineral fine powder.
  • Examples of liquid carriers include organic solvents and water.
  • Examples of the surfactants include anionic surfactants, nonionic surfactants, and cationic surfactants.
  • Examples of other auxiliary agents for formulation include thickeners, preservatives, and colorants.
  • composition of the present invention is prepared by adjusting the amounts of the mefentrifluconazole-containing formulation, the oil adjuvant, and water, such that each of the concentrations of mefentrifluconazole and the oil adjuvant in the composition of the present invention falls within the above ranges, and mixing them.
  • composition of the present invention may further comprise one or more other fungicides and/or insecticides, and the mefentrifluconazole-containing formulation may comprise fungicides and/or insecticides other than mefentrifluconazole.
  • Plant diseases can be controlled by applying the composition of the present invention to a plant or soil for cultivating the plant. Especially, without significantly increasing phytotoxicity, plant diseases can be controlled by applying the composition of the present invention.
  • Examples of the plant diseases that can be controlled by the present invention include the following plant diseases.
  • Rice diseases blast (Magnaporthe grisea), brown spot (Cochliobolus miyabeanus), sheath blight (Rhizoctonia solani), and bakanae disease (Gibberella fujikuroi); Wheat diseases: powdery mildew (Erysiphe graminis), fusarium Head blight (Fusarium graminearum, F. avenaceum, F. culmorum, Microdochium nivale), rust (for example, yellow rust (Puccinia striiformis), black rust (P. graminis), Brown rust (P.
  • Citrus diseases melanose (Diaporthe citri), scab (Elsinoe fawcetti), and fruit rot (Penicillium digitatum, P. italicum); Apple diseases: blossom blight (Monilinia mali), canker (Valsa ceratosperma), powdery mildew (Podosphaera leucotricha), Alternaria leaf spot (Alternaria alternata apple pathotype), scab (Venturia inaequalis), and bitter rot (Colletotrichum acutatum); Pear diseases: scab (Venturia nashicola, V.
  • Soybean diseases purple stain (Cercospora kikuchii), Sphaceloma scad (Elsinoe glycines), pod and stem blight (Diaporthe phaseolorum var. sojae), septoria brown spot (Septoria glycines), Cercospora leaf spot (Cercospora sojina), rust (Phakopsora pachyrhizi), damping-off caused by rhizoctonia fungus (Rhizoctonia solani), target spot (Corynespora casiicola), and sclerotinia rot (Sclerotinia sclerotiorum); Kidney bean diseases: anthracnose (Colletotrichum lindemthianum); Peanut diseases: leaf spot (Cercospora personata), brown leaf spot (Cercospora arachidicola), and southern blight (Sclerotium rolfsii); Garden pea diseases: powdery milde
  • plants to which the composition of the present invention can be applied include the following plants.
  • Crops corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, azuki bean, kidney bean, peanut, buckwheat, sugar beet, rapeseed, sunflower, sugar cane, tobacco, and the others;
  • Vegetables Solanaceous vegetables (for example, eggplant, tomato, green pepper, hot pepper, or potato), Cucurbitaceous vegetables (for example, cucumber, pumpkin, zucchini, watermelon, melon, or squash), Cruciferous vegetables (for example, Japanese radish, white turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, leaf mustard, broccoli, or cauliflower), Asteraceous vegetables (for example, burdock, garland chrysanthemum, artichoke, or lettuce), Liliaceous vegetables (for example, welsh onion, onion, garlic, or asparagus), Ammiaceous vegetables (for example, carrot, parsley, celery, or parsnip), Chenopodiaceous vegetables (for example, spinach, or Swiss
  • the plants may be plants provided with tolerance by gene recombination technology.
  • the method for controlling plant diseases according to the present invention includes the steps of: mixing a mefentrifluconazole-containing formulation, an oil adjuvant, and water to prepare the composition of the present invention; and applying the composition of the present invention to a plant or soil for cultivating the plant.
  • the step of preparing the composition of the present invention is performed by the method described above.
  • the step of applying the composition of the present invention is carried out by ground application or aerial application. In the step of applying the composition of the present invention, the composition of the present invention is applied with a ground sprayer, an aerial equipment or through a sprinkler irrigation equipment.
  • the application rate of the composition of the present invention in the method of the present invention may be varied depending on a type of plant, a type or a frequency of an occurrence of plant diseases to be controlled, a formulation type, an application period, an application method, an application site, a climate condition and the like.
  • the application rate of the composition of the present invention is usually 10 to 100 g per hectare as an amount of mefentrifluconazole.
  • Liquid compositions comprising 150 ppm of mefentrifluconazole, 2 or 6% by volume of an oil adjuvant and water (hereinafter referred to as Present Composition 1 and Present Composition 2) were prepared by diluting mefentrifluconazole SC and an oil adjuvant (COC: Agri-Dex, containing 82% of heavy range paraffinic oil, 17% of surfactant, and 1% of other components, manufactured by Helena), respectively, with water and mixing them.
  • COC Agri-Dex
  • a liquid composition comprising 150 ppm of mefentrifluconazole and water (hereinafter referred to as Comparative Composition 1), a liquid composition comprising 2% by volume of an oil adjuvant and water (hereinafter referred to as Comparative Composition 2), and a liquid composition comprising 6% by volume of an oil adjuvant and water (hereinafter referred to as Comparative Composition 3), respectively.
  • Comparative Composition 1 a liquid composition comprising 150 ppm of mefentrifluconazole and water
  • Comparative Composition 2 a liquid composition comprising 2% by volume of an oil adjuvant and water
  • Comparative Composition 3 a liquid composition comprising 6% by volume of an oil adjuvant and water
  • the prepared liquid compositions were each sprayed to the foliage of wheat such that the application rate would be 200 L/ha. After spraying, the plant was air-dried, and an aqueous suspension of spores of Brown rust (P. recondita) was inoculated by spraying it. After inoculating, the plant was placed at 23°C under high humidity for 1 day and subsequently placed under illumination for 10 days, then the lesion area was investigated (lesion area in the treated area). On the other hand, in the non-treated area, the same operation as in the treated area was carried out except that the liquid composition was not sprayed, and the lesion area of Brown rust in the non-treated area was investigated (lesion area in the non-treated area).
  • Liquid compositions comprising 500 or 1000 ppm of mefentrifluconazole, 2 or 6% by volume of an oil adjuvant and water (hereinafter referred to as Present Composition 3, Present Composition 4, Present Composition 5, and Present Composition 6) were prepared by diluting mefentrifluconazole SC and an oil adjuvant (COC: Agri-Dex, containing 82% of heavy range paraffinic oil, 17% of surfactant, and 1% of other components, manufactured by Helena), respectively, with water and mixing them.
  • COC Agri-Dex
  • mefentrifluconazole SC was alone diluted with water to prepare a liquid composition comprising 500 or 1000 ppm of mefentrifluconazole and water (hereinafter referred to as Comparative Composition 4 and Comparative Composition 5).
  • Comparative Composition 4 mefentrifluconazole SC
  • Comparative Composition 5 mefentrifluconazole SC
  • Comparative Composition 6 Comparative Composition 7
  • Comparative Composition 8 Comparative Composition 9
  • Comparative Composition 11 Comparative Composition 11
  • Fenbuconazole SC was purchased from a public source as Indar Flowable (22% fenbuconazole) manufactured by Dow Agrosciences Japan KK.
  • a soil was filled into a plastic pot, and wheat (variety: Apogee) was seeded therein, and grown in a greenhouse for 45 days, and an aqueous suspension of spores of Septoria tritici was inoculated by spraying it. After spraying, the plant was placed at 15°C under high humidity for 1 day and subsequently placed under illumination for 6 days. The prepared liquid compositions were each sprayed to the foliage of wheat such that the application rate would be 100 L/ha. The sprayed plant was placed for further 17 days, then the lesion area was investigated (lesion area in the treated area).
  • the same operation as in the treated area was carried out except that the liquid composition was not sprayed, and the lesion area of Septoria tritici in the non-treated area was investigated (lesion area in the non-treated area). From the lesion area in each of the treated area and the non-treated area, the efficacy of the treated area was determined according to the above “Formula 1”. The results are indicated in Table 2.
  • Liquid compositions comprising 10,000 ppm of mefentrifluconazole, 1.25 or 10% by volume of an oil adjuvant and water (hereinafter referred to as Present Composition 7 and Present Composition 8) were prepared by diluting mefentrifluconazole SC and an oil adjuvant (COC: Agri-Dex, containing 82% of heavy range paraffinic oil, 17% of surfactant, and 1% of other components, manufactured by Helena), respectively, with water and mixing them.
  • COC Agri-Dex
  • liquid compositions (hereinafter referred to as Present Composition 9 and Present Composition 10) were prepared by replacing Agri-Dex with Sundance II (MSO, containing 90% of methylated seed oil and 10% of alkyl and aryl alkoxylates and phosphate esters).
  • MSO Sundance II
  • Present Composition 11 and Present Composition 12 liquid compositions (hereinafter referred to as Present Composition 11 and Present Composition 12) were prepared by replacing Agri-Dex with Destiny (HSOC, containing 50% of methylated seed oil, 42% of sorbitan fatty acid esters and high fructose corn syrup, and 8% of other ingredients).
  • mefentrifluconazole SC was alone diluted with water to prepare a liquid composition comprising 10,000 ppm of mefentrifluconazole and water (hereinafter referred to as Mefentrifluconazole no-adjuvant 10).
  • Mefentrifluconazole no-adjuvant 10 mefentrifluconazole SC with fenbuconazole SC (hereinafter referred to as Comparative Composition 12, Comparative Composition 13, Comparative Composition 14, Comparative Composition 15, Comparative Composition 16, Comparative Composition 17, and Fenbuconazole no-adjuvant 10).
  • Fenbuconazole SC was purchased from a public source as Indar Flowable (22% fenbuconazole) manufactured by Dow Agrosciences Japan KK.
  • a soil was filled into a plastic pot, and corn (variety: Pioneer) was seeded therein, and grown in a greenhouse for 4 days.
  • the prepared liquid compositions were each dripped into the whorl of emerged corn plants at a rate of 20 micro liters per plant. After dripping, the plants were placed in the greenhouse for 8 days, then the plant lengths were measured. Some plants were not dripped with any composition as a non-treated control and were handled in the same manner in the greenhouse. From the plant lengths in each of the treated plants and the non-treated plants, the relative length of the compositions was determined according to the following “Formula 2”. The results are indicated in Table 3. Mefentrifluconazole and fenbuconazole each retarded corn plant slightly without adjuvant.
  • Relative length (%) (length of the treated plant/length of the non-treated plant) ⁇ 100
  • a liquid composition comprising 2,000 ppm of mefentrifluconazole, 10% by volume of an oil adjuvant and water (hereinafter referred to as Present Composition 13) were prepared by diluting mefentrifluconazole SC and an oil adjuvant (COC: Agri-Dex, containing 82% of heavy range paraffinic oil, 17% of surfactant, and 1% of other components, manufactured by Helena) with water and mixing them.
  • COC Agri-Dex, containing 82% of heavy range paraffinic oil, 17% of surfactant, and 1% of other components, manufactured by Helena
  • a liquid compositions (hereinafter referred to as Present Composition 14) were prepared by replacing Agri-Dex with Sundance II (MSO, containing 90% of methylated seed oil and 10% of alkyl and aryl alkoxylates and phosphate esters).
  • a liquid composition (hereinafter referred to as Present Composition 15) were prepared by replacing Agri-Dex with Destiny (HSOC, containing 50% of methylated seed oil, 42% of sorbitan fatty acid esters and high fructose corn syrup, and 8% of other ingredients).
  • mefentrifluconazole SC was alone diluted with water to prepare a liquid composition comprising 2,000 ppm of mefentrifluconazole and water (hereinafter referred to as Mefentrifluconazole no-adjuvant 2).
  • Mefentrifluconazole no-adjuvant 2 mefentrifluconazole SC with fenbuconazole SC
  • Comparative Composition 18 Comparative Composition 19
  • Comparative Composition 20 Comparative Composition 20
  • Fenbuconazole no-adjuvant 2 Fenbuconazole SC was purchased from a public source as Indar Flowable (22% fenbuconazole) manufactured by Dow Agrosciences Japan KK.
  • a soil was filled into a plastic pot, and corn (variety: Pioneer) was seeded therein, and grown in a greenhouse for 4 days.
  • the prepared liquid compositions were each sprayed onto the emerged corn plants at a rate of 1000 L/ha. After spraying, the plants were placed in the greenhouse for 8 days, then the plant lengths were measured. Some plants were not sprayed with any composition as a non-treated control and were handled in the same manner in the greenhouse. From the plant lengths in each of the treated plants and the non-treated plants, the relative length of the compositions was determined according to the above “Formula 2”. The results are indicated in Table 4. Mefentrifluconazole and fenbuconazole each did not effect on plant length without adjuvant. However, the addition of oil adjuvants enhanced the retardation by fenbuconazole while the addition slightly enhance the plant length in mefentrifluconazole treatments.

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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

Un objet de la présente invention est de fournir une composition qui présente un excellent effet de lutte contre les maladies des plantes. Une composition liquide comprenant une quantité efficace de mefentrifluconazole, de 0,1 à 10 % en volume d'un adjuvant huileux, et de l'eau.
PCT/JP2020/021216 2019-05-31 2020-05-28 Composition liquide comprenant du mefentrifluconazole WO2020241788A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
AU2020283106A AU2020283106A1 (en) 2019-05-31 2020-05-28 Liquid composition comprising mefentrifluconazole
US17/614,921 US20220248674A1 (en) 2019-05-31 2020-05-28 Liquid composition comprising mefentrifluconazole
BR112021024061A BR112021024061A2 (pt) 2019-05-31 2020-05-28 Composição líquida compreendendo mefentrifluconazol
CA3142280A CA3142280A1 (fr) 2019-05-31 2020-05-28 Composition liquide comprenant du mefentrifluconazole

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP2019-102242 2019-05-31
JP2019102242 2019-05-31
US201916507619A 2019-07-10 2019-07-10
US16/507619 2019-07-10

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WO2020241788A1 true WO2020241788A1 (fr) 2020-12-03

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BR (1) BR112021024061A2 (fr)
CA (1) CA3142280A1 (fr)
WO (1) WO2020241788A1 (fr)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999026472A1 (fr) * 1997-11-25 1999-06-03 Cognis Corporation Utilisation d'ethoxylates d'alcools gras a gamme etroite dans des formulations d'adjuvants et de pesticides agricoles
WO2013162725A1 (fr) * 2012-04-25 2013-10-31 Bayer Cropscience Lp Co-cristaux de métalaxyl et de prothioconazole et leurs procédés de fabrication et d'utilisation
JP2014094909A (ja) * 2012-11-08 2014-05-22 Sumitomo Chemical Co Ltd 除草用組成物
US20140155262A1 (en) * 2011-07-13 2014-06-05 Basf Se Fungicidal substituted 2-[2-halogenalkyl-4-(phenoxy)-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds
CN106359395A (zh) * 2016-08-30 2017-02-01 佛山市盈辉作物科学有限公司 一种含有苯并烯氟菌唑的杀菌组合物

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999026472A1 (fr) * 1997-11-25 1999-06-03 Cognis Corporation Utilisation d'ethoxylates d'alcools gras a gamme etroite dans des formulations d'adjuvants et de pesticides agricoles
US20140155262A1 (en) * 2011-07-13 2014-06-05 Basf Se Fungicidal substituted 2-[2-halogenalkyl-4-(phenoxy)-phenyl]-1-[1,2,4]triazol-1-yl-ethanol compounds
WO2013162725A1 (fr) * 2012-04-25 2013-10-31 Bayer Cropscience Lp Co-cristaux de métalaxyl et de prothioconazole et leurs procédés de fabrication et d'utilisation
JP2014094909A (ja) * 2012-11-08 2014-05-22 Sumitomo Chemical Co Ltd 除草用組成物
CN106359395A (zh) * 2016-08-30 2017-02-01 佛山市盈辉作物科学有限公司 一种含有苯并烯氟菌唑的杀菌组合物

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AU2020283106A1 (en) 2022-01-06
CA3142280A1 (fr) 2020-12-03

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