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WO2012020777A1 - Composition de lutte contre les maladies des plantes et utilisation de celle-ci - Google Patents

Composition de lutte contre les maladies des plantes et utilisation de celle-ci Download PDF

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Publication number
WO2012020777A1
WO2012020777A1 PCT/JP2011/068199 JP2011068199W WO2012020777A1 WO 2012020777 A1 WO2012020777 A1 WO 2012020777A1 JP 2011068199 W JP2011068199 W JP 2011068199W WO 2012020777 A1 WO2012020777 A1 WO 2012020777A1
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Prior art keywords
parts
pyridazine compound
present
compound
present pyridazine
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Japanese (ja)
Inventor
雄一 松崎
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Sumitomo Chemical Co Ltd
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Sumitomo Chemical Co Ltd
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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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines

Definitions

  • the present invention relates to a plant disease control composition and its use.
  • Patent Document 1 Conventionally, many compounds have been developed and put to practical use in order to control plant diseases (see, for example, Patent Document 1).
  • An object of the present invention is to provide a composition having an excellent control effect against plant diseases.
  • the present invention provides a plant disease control composition containing a pyridazine compound represented by the following formula (I) and one or more carboxamide compounds selected from the following group (A).
  • the composition has an excellent control effect against physical diseases. That is, the present invention is as follows. [1] Formula (I) [Where, R 1 represents a chlorine atom, a bromine atom, a cyano group, a methyl group or a methoxy group, R 2 represents a fluorine atom or a hydrogen atom, R 3 represents a halogen atom, R 4 represents a halogen atom, a methoxy group or a hydrogen atom.
  • a pyridazine compound represented by A plant disease control composition comprising one or more carboxamide compounds selected from the group (A).
  • the plant disease control composition according to [1], wherein the weight ratio of the pyridazine compound and the carboxamide compound is pyridazine compound / carboxamide compound 0.1 / 1 to 10/1.
  • a pyridazine compound represented by A method for controlling plant diseases comprising a step of treating an effective amount with one or more carboxamide compounds selected from the group (A) on a plant or soil for growing plants.
  • the plant disease control method according to [3], wherein the weight ratio of the pyridazine compound to the carboxamide compound is pyridazine compound / carboxamide compound 0.1 / 1 to 10/1.
  • the plant disease control method according to [3] or [4], wherein the plant or the soil in which the plant is cultivated is wheat or soil in which the wheat is cultivated.
  • plant diseases can be controlled.
  • the plant disease control composition of the present invention (hereinafter referred to as the present composition) has the formula (I) [Where, R 1 represents a chlorine atom, a bromine atom, a cyano group, a methyl group or a methoxy group, R 2 represents a fluorine atom or a hydrogen atom, R 3 represents a halogen atom, R 4 represents a halogen atom, a methoxy group or a hydrogen atom. ] And one or more carboxamide compounds selected from the group (A) (hereinafter referred to as the present carboxamide compound).
  • examples of the halogen atom represented by each of R 3 and R 4 include a chlorine atom, a bromine atom, and a fluorine atom.
  • Examples of the present pyridazine compound include the following pyridazine compounds.
  • R 1 is a chlorine atom
  • R 2 is a fluorine atom
  • R 3 is a chlorine atom
  • R 4 is a chlorine atom
  • R 1 is a bromine atom
  • R 2 is a fluorine atom
  • R 3 is a chlorine atom
  • R 4 is a chlorine atom (hereinafter referred to as the present pyridazine compound (2)).
  • R 1 is a cyano group
  • R 2 is a fluorine atom
  • R 3 is a chlorine atom
  • R 4 is a chlorine atom
  • R 1 is a methyl group
  • R 2 is a fluorine atom
  • R 3 is a chlorine atom
  • R 4 is a chlorine atom (hereinafter referred to as the present pyridazine compound (4)).
  • R 1 is a methoxy group
  • R 2 is a fluorine atom
  • R 3 is a chlorine atom
  • R 4 is a chlorine atom
  • R 1 is a chlorine atom
  • R 2 is a hydrogen atom
  • R 3 is a chlorine atom
  • R 4 is a chlorine atom (hereinafter referred to as the present pyridazine compound (6)).
  • a pyridazine compound in which R 1 is a chlorine atom, a bromine atom, a methyl group or a methoxy group in formula (I) is produced, for example, by the method described in International Publication No. 2007/066601 pamphlet. be able to.
  • the compound (I-2) in which R 1 is a cyano group in the formula (I) is, for example, the compound in the formula (I) in which R 1 is a bromine atom. It can be produced by reacting I-1) with copper cyanide. [Wherein R 2 , R 3 and R 4 represent the same meaning as described above. ] The reaction is usually performed in the presence of a solvent. Examples of the solvent used in the reaction include aprotic polar solvents such as N, N-dimethylacetamide. The amount of copper cyanide used in the reaction is usually 1 to 1.5 mol per 1 mol of compound (I-1).
  • the reaction temperature is usually in the range of 120 to 180 ° C., and the reaction time is usually in the range of 1 to 24 hours.
  • the reaction mixture is mixed with water and an organic solvent and then filtered, the filtrate is separated, and the resulting organic layer is further washed with water, dried and concentrated.
  • Compound (I-2) can be isolated.
  • Compound (I-2) can be further purified by chromatography, recrystallization and the like.
  • the compound (I-4) in which R 1 is a methyl group in the formula (I) is the compound (I-) in which the R 1 is a chlorine atom in the formula (I) among the pyridazine compounds. 3) is converted to formula (II) [Wherein, X represents a bromine atom or a chlorine atom. ] It can manufacture by making it react with the Grignard reagent shown by presence of an iron catalyst. [Wherein R 2 , R 3 and R 4 represent the same meaning as described above. ] The reaction is usually performed in the presence of a solvent.
  • Examples of the solvent used in the reaction include tetrahydrofuran, diethyl ether and N-methylpyrrolidone, and mixed solvents thereof.
  • the reaction solvent is a mixture of tetrahydrofuran and N-methylpyrrolidone
  • the mixing ratio of tetrahydrofuran and N-methylpyrrolidone is usually in the range of 30: 1 to 3: 1 by volume ratio.
  • Examples of the iron catalyst used in the reaction include acetylacetone iron (III) and iron (III) chloride.
  • the amount of the iron catalyst used is usually in a proportion of 0.01 to 0.3 mol per 1 mol of compound (I-3).
  • the reaction temperature of the reaction is usually in the range of ⁇ 20 ° C.
  • reaction time is usually in the range of 0.1 to 6 hours.
  • the reaction mixture is mixed with hydrochloric acid and extracted with an organic solvent, and the resulting organic layer is washed with water, dried, concentrated, and the like, so that the compound (I-4) is obtained. Can be separated.
  • the isolated compound (I-4) can be further purified by chromatography, recrystallization and the like.
  • the composition of the present invention may be a mixture of the pyridazine compound and the carboxamide compound itself, but the composition of the present invention is usually mixed with the pyridazine compound, the carboxamide compound and an inert carrier, and if necessary, a surface active agent. It is formulated into oils, emulsions, flowables, wettable powders, granular wettable powders, powders, granules and the like by adding additives and other formulation adjuvants. Such a preparation can be used as a plant disease control agent as it is or with addition of other inactive ingredients.
  • the present composition contains the present pyridazine compound and the present carboxamide compound in a total amount of usually 0.1 to 99% by weight, preferably 0.2 to 90% by weight, more preferably 1 to 80% by weight.
  • solid carriers used in formulation include kaolin clay, attapulgite clay, bentonite, montmorillonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, corn cob flour, walnut shell powder, etc.
  • Natural organic materials synthetic organic materials such as urea, salts such as calcium carbonate and ammonium sulfate, fine powders or granular materials made of synthetic inorganic materials such as synthetic silicon hydroxide, etc.
  • liquid carriers include, for example, xylene, alkylbenzene, methyl Aromatic hydrocarbons such as naphthalene, alcohols such as 2-propanol, ethylene glycol, propylene glycol and ethylene glycol monoethyl ether, ketones such as acetone, cyclohexanone and isophorone, vegetable oils such as soybean oil and cottonseed oil, petroleum fats Group hydrocarbon , Esters, dimethyl sulfoxide, acetonitrile and water.
  • surfactants include anionic interfaces such as alkyl sulfate esters, alkylaryl sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkylaryl ether phosphate esters, lignin sulfonates, naphthalene sulfonate formaldehyde polycondensates, and the like.
  • Activators, and nonionic surfactants such as polyoxyethylene alkyl aryl ethers, polyoxyethylene alkyl polyoxypropylene block copolymers, sorbitan fatty acid esters, and cationic surfactants such as alkyltrimethylammonium salts.
  • formulation adjuvants include, for example, water-soluble polymers such as polyvinyl alcohol and polyvinylpyrrolidone, gum arabic, alginic acid and its salts, polysaccharides such as CMC (carboxymethyl cellulose) and xanthan gum, aluminum magnesium silicate, alumina sol Inorganic substances such as preservatives, colorants and stabilizers such as PAP (isopropyl acid phosphate) and BHT.
  • water-soluble polymers such as polyvinyl alcohol and polyvinylpyrrolidone
  • gum arabic alginic acid and its salts
  • polysaccharides such as CMC (carboxymethyl cellulose) and xanthan gum
  • aluminum magnesium silicate such as aluminum magnesium silicate
  • alumina sol Inorganic substances such as preservatives, colorants and stabilizers such as PAP (isopropyl acid phosphate) and BHT.
  • PAP isopropyl acid phosphate
  • composition of the present invention is also prepared by formulating the present pyridazine compound and the present carboxamide compound by the above-mentioned methods, diluting with water as necessary, and mixing the respective formulations or their dilutions. You can also
  • composition of the present invention can be used to protect plants from plant diseases.
  • Examples of plant diseases for which the composition of the present invention has a controlling effect include the following.
  • Rice diseases rice blast (Magnaporthe grisea), sesame leaf blight (Cochliobolus miyabeanus), blight (Rhizoctonia solani), idiotic seedling (Gibberella fujikuruoi).
  • Wheat diseases powdery mildew (Erysiphe graminis), red mold disease (Fusarium gramaminerum, F. avenacerum, F. culmorum, Microdochium nitrid, red rust (Puccinia isp.
  • Ustilago nuda Ustilago nuda
  • cloud disease Rhynchosporium secalis
  • reticular disease Pyrenophora teres
  • spot disease Cochliobolus sativus
  • leafy leaf disease Pyrenophora graminea
  • Rhizonia a Diseases of corn: smut (Ustilago maydis), sesame leaf blight (Cochliobolus heterostrohus), leprosy (Gloeocercospora sorgi), southern rust (Puccinia polysora), gray leaf spot disease Rhizoctonia solani due to seedling.
  • Oyster diseases Anthracnose (Gloeosporium kaki), deciduous leaf disease (Cercospora kaki, Mycosphaerella nawae). Diseases of cucurbits: anthracnose (Colletotrichum lagenarium), powdery mildew (Sphaerotheca fuliginea), vine blight (Mycosphaerella meloniis), vine scab (Fusarium oxysporum), pori (pure disease) ), Seedling blight (Pythium sp.); Diseases of tomato: Alternaria solani, leaf mold (Cladosporium fulvum), plague (Phytophthora infestans).
  • soybean Purpura (Cercospora kikuchii), black scab (Elsinoe glycines), black spot (Diaporthe phaseolum var. Sojae), brown spot (Septoria glycines) Phytophthora sojae, Rhizoctonia solani, Corynespora casiicola, Sclerotinia sclerotiorum. Kidney disease: Anthracnose (Colletotrichum lindemthianum). Peanut disease: black astringency (Cercospora personata), brown spot (Cercospora arachidicola), white silkworm (Sclerotium rolfsii).
  • Pea disease powdery mildew (Erysiphe pisi). Potato diseases: Alternaria solani, Phytophthora infestans, Sputum rot septica, Spongosporia subteranean f.
  • Strawberry disease powdery mildew (Sphaerotheca humuli), anthracnose (Glomerella singulata). Tea diseases: net blast (Exobasidium reticulatum), white scab (Elsinoe leucospila), ring spot disease (Pestarotropis sp.), Anthracnose (Colletotrichum theae-sinensis).
  • Tobacco disease Alternaria longipes, powdery mildew (Erysiphe cichoracearum), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina), epidemic (Phytophyti. Rapeseed diseases: Sclerotinia sclerotiorum, Rhizoctonia solani, and Rhizoctonia solani. Cotton disease: Rhizoctonia solani caused by Rhizoctonia spp. Diseases of sugar beet: brown spot disease (Cercospora beticola), leaf rot (Thanatephorus cucumeris), root rot (Thanatephorus cucumeris), black root disease (Aphanomyces cochlioides).
  • Rose diseases black spot (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa), downy mildew (Peronospora sparsa).
  • Diseases of chrysanthemum and asteraceae vegetables downy mildew (Bremia lactucae), brown spot disease (Septoria chrysanthemi-indici), white rust (Puccinia horiana).
  • Diseases of various crops Diseases caused by Pythium spp.
  • Aspergillus genus Penicillium genus, Fusarium genus, Gibberella genus, Tricoderder genus, Thielaviopsis genus, Rhizopus genus, Mucor genus, Corticium genus, Phoma genus, Rhizoctonia genus Disease. Viral diseases of various crops mediated by Polymixa genus or Olpidium genus.
  • Agricultural crops corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, buckwheat, sugar beet, rapeseed, sunflower, sugarcane, tobacco, etc.
  • Vegetables Eggplant vegetables (eggplant, tomatoes, peppers, peppers, potatoes, etc.), cucurbits vegetables (cucumbers, pumpkins, zucchini, watermelon, melon, squash, etc.), cruciferous vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage) , Cabbage, mustard, broccoli, cauliflower, etc.), asteraceae vegetables (burdock, garlic, artichoke, lettuce, etc.), liliaceae vegetables (leek, onion, garlic, asparagus), celery family vegetables (carrot, parsley, celery, USA) Bowfish, etc.), red crustacean vegetables (spinach, chard, etc.), perilla vegetables (perilla, mint, basil, etc.), strawberries, sweet potatoes, yam, taros, etc.
  • Trees other than fruit trees Cha, mulberry, flowering trees, street trees (ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, oak, poplar, redwood, fu, sycamore, zelkova, black bean, peach tree, Tsuga, rat, pine, Spruce, yew) etc.
  • the above-mentioned plant may be a plant imparted with resistance by genetic recombination technology.
  • wheat diseases that are expected to have particularly high efficacy include powdery mildew (Erysiphe graminis), red mold disease (Fusarium gramaminerum, F. avenacerum, F. culmorum, Microdochium). nivale, rust disease (Puccinia striformis, P. graminis, P.
  • red snow rot (Micronetriella nivale), snow rot microspora nuclear disease (Typhula sp.), naked scab (Ustira scab) (Tilletia caries), eye spot disease (Pseudocercosporella herpotriochoides), leaf blight (Myco) sphaerella gramicola), blight (Stagonospora nodorum), macular disease (Pyrenophora tritici-repentis); Etc.
  • composition the following are mentioned, for example.
  • a composition comprising the present pyridazine compound (4) and bixaphene; A composition containing the present pyridazine compound (4) and isopyrazam; A composition containing the pyridazine compound (4) and boscalid; A composition containing the present pyridazine compound (4) and fluopyram; A composition comprising the present pyridazine compound (4) and floxapyroxad; A composition containing the present pyridazine compound (4) and sedaxane; A composition containing the pyridazine compound (4) and penflufen; A composition containing the present pyridazine compound (4) and flutolanil; A composition containing the present pyridazine compound (4) and mepronil; A composition containing the present pyridazine compound (4) and carboxin; A composition containing the present pyridazine compound (4) and tifluzamide; A composition containing the
  • a composition comprising the present pyridazine compound (6) and bixaphene; A composition containing the present pyridazine compound (6) and isopyrazam; A composition containing the present pyridazine compound (6) and boscalid; A composition containing the present pyridazine compound (6) and fluopyram; A composition comprising the present pyridazine compound (6) and floxapyroxad; A composition containing the pyridazine compound (6) and sedaxane; A composition containing the pyridazine compound (6) and penflufen; A composition containing the present pyridazine compound (6) and flutolanil; A composition comprising the present pyridazine compound (6) and mepronil; A composition containing the present pyridazine compound (6) and carboxin; A composition containing the present pyridazine compound (6) and tifluzamide; A composition containing the
  • a composition comprising the present pyridazine compound (1) and bixaphene in a weight ratio of the present pyridazine compound (1) /bixafen 0.1/1 to 10/1;
  • a composition comprising the present pyridazine compound (1) and isopyrazam in a weight ratio of the present pyridazine compound (1) /isopyrazam 0.1/1 to 10/1;
  • a composition comprising the present pyridazine compound (1) and boscalid in a weight ratio of the present pyridazine compound (1) /boscalid 0.1/1 to 10/1;
  • a composition comprising the present pyridazine compound (1) and fluopyram in a weight ratio of the present pyridazine compound (1) /fluopyram 0.1/1 to 10/1;
  • a composition comprising the present pyridazine compound (2) and bixafen in a weight ratio of the present pyridazine compound (2) /bixafen 0.1/1 to 10/1;
  • a composition comprising the present pyridazine compound (2) and isopyrazam in a weight ratio of the present pyridazine compound (2) /isopyrazam 0.1/1 to 10/1;
  • a composition comprising the present pyridazine compound (2) and boscalid in a weight ratio of the present pyridazine compound (2) /boscalid 0.1/1 to 10/1;
  • a composition comprising the present pyridazine compound (2) and fluopyram in a weight ratio of the present pyridazine compound (2) /fluopyram 0.1/1 to 10/1;
  • a composition comprising the present pyridazine compound (3) and bixaphene in a weight ratio of the present pyridazine compound (3) /bixafen 0.1/1 to 10/1;
  • a composition comprising the present pyridazine compound (3) and isopyrazam in a weight ratio of the present pyridazine compound (3) /isopyrazam 0.1/1 to 10/1;
  • a composition comprising the present pyridazine compound (3) and boscalid in a weight ratio of the present pyridazine compound (3) /boscalid 0.1/1 to 10/1;
  • a composition comprising the present pyridazine compound (3) and fluopyram in a weight ratio of the present pyridazine compound (3) /fluopyram 0.1/1 to 10/1;
  • a composition comprising the present pyridazine compound (4) and bixaphene in a weight ratio of the present pyridazine compound (4) /bixafen 0.1/1 to 10/1;
  • a composition comprising the present pyridazine compound (4) and isopyrazam in a weight ratio of the present pyridazine compound (4) /isopyrazam 0.1/1 to 10/1;
  • a composition comprising the present pyridazine compound (4) and boscalid in a weight ratio of the present pyridazine compound (4) /boscalid 0.1/1 to 10/1;
  • a composition comprising the present pyridazine compound (4) and fluopyram in a weight ratio of the present pyridazine compound (4) /fluopyram 0.1/1 to 10/1;
  • a composition comprising the present pyridazine compound (5) and bixafen in a weight ratio of the present pyridazine compound (5) /bixafen 0.1/1 to 10/1;
  • a composition comprising the present pyridazine compound (5) and isopyrazam in a weight ratio of the present pyridazine compound (5) /isopyrazam 0.1/1 to 10/1;
  • a composition comprising the present pyridazine compound (5) and boscalid in a weight ratio of the present pyridazine compound (5) /boscalid 0.1/1 to 10/1;
  • a composition comprising the present pyridazine compound (5) and fluopyram in a weight ratio of the present pyridazine compound (5) /fluopyram 0.1/1 to 10/1;
  • a composition comprising the present pyridazine compound (6) and bixafen in a weight ratio of the present pyridazine compound (6) /bixafen 0.1/1 to 10/1;
  • a composition comprising the present pyridazine compound (6) and isopyrazam in a weight ratio of the present pyridazine compound (6) /isopyrazam 0.1/1 to 10/1;
  • a composition comprising the present pyridazine compound (6) and boscalid in a weight ratio of the present pyridazine compound (6) /boscalid 0.1/1 to 10/1;
  • a composition comprising the present pyridazine compound (6) and fluopyram in a weight ratio of the present pyridazine compound (6) /fluopyram 0.1/1 to 10/1;
  • the plant disease control method of the present invention (hereinafter referred to as the present invention control method) is carried out by treating an effective amount of the present pyridazine compound and the present carboxamide compound on the plant or the soil where the plant is grown.
  • plants include, for example, plant foliage, plant seeds and plant bulbs.
  • a bulb means here a bulb, a bulb, a rhizome, a tuber, a tuberous root, and a root support body.
  • the pyridazine compound and the carboxamide compound may be treated separately on the plant or the soil where the plant is cultivated at the same time, but the composition of the present invention is usually used from the viewpoint of simplicity during the treatment. Is processed as
  • examples of the treatment method of the pyridazine compound and the carboxamide compound include foliage treatment, soil treatment, root treatment, and seed treatment.
  • foliage treatment examples include a method of treating the surface of a plant being cultivated by foliage spraying and tree trunk spraying.
  • examples of the root treatment include a method of immersing the whole plant or root in a chemical solution containing the pyridazine compound and the carboxamide compound, and a solid preparation containing the pyridazine compound, the carboxamide compound and a solid carrier. The method of making it adhere to the root part of a plant is mentioned.
  • soil treatment examples include soil application, soil mixing, and chemical irrigation into soil.
  • seed treatment includes, for example, treatment of the seed or bulb of a plant to be protected from plant diseases, and specifically, for example, a seed of a suspension of the composition of the present invention is made into a mist.
  • Spraying treatment for spraying on the surface or the surface of the bulb adding a small amount of water to the wettable powder, emulsion or flowable agent of the composition of the present invention, or applying the composition to the seed or bulb as it is, composition of the present invention
  • dipping treatment in which seeds are immersed in the solution for a certain time film coating treatment and pellet coating treatment.
  • the treatment amount of the present pyridazine compound and the present carboxamide compound is the kind of plant to be treated, the kind and occurrence frequency of plant diseases to be controlled, the formulation form, the treatment time, the treatment method, the treatment place, the weather. It depends on conditions.
  • the treatment amount is a total amount of the present pyridazine compound and the present carboxamide compound, usually 1 to 500 g per 1000 m 2 , preferably 2 ⁇ 200 g, more preferably 10 ⁇ 100 g.
  • the treatment amount of the present pyridazine compound and the present carboxamide compound in the treatment of seeds is the total amount of the present pyridazine compound and the present carboxamide compound, and is usually 0.001 to 10 g, preferably 0.01 to 1 g, per 1 kg of seed. It is.
  • the above emulsion, wettable powder, flowable agent and the like are usually treated by diluting with water and spraying.
  • the concentration of the present pyridazine compound and the present carboxamide compound is generally 0.0005 to 2% by weight, preferably 0.005 to 1% by weight, as the total concentration of the present pyridazine compound and the present carboxamide compound.
  • the above powders, granules and the like are usually processed as they are without dilution.
  • Reference production example 1 1.41 g of triethylamine was added dropwise to a mixture of 1.85 g of 2-bromo-4′-fluoropropiophenone, 2.06 g of 3,5-dichloro-2-pyridylacetic acid and 30 mL of acetonitrile in a water bath at room temperature for 4 hours. After stirring, the mixture was allowed to stand overnight. 30 mL of acetonitrile was added to the mixture, and 4.56 g of 1,8-diazabicyclo [5.4.0] -7-undecene (hereinafter referred to as DBU) was added dropwise under ice cooling. The mixture was stirred at room temperature for 1 hour.
  • DBU 1,8-diazabicyclo [5.4.0] -7-undecene
  • Reference production example 2 4- (3,5-dichloro-2-pyridyl) -5- (4-fluorophenyl) -6-methyl-2H-pyridazin-3-one 2.45 g and phosphorus oxybromide 8.0 g The mixture was stirred at a temperature of 100 ° C. for 1 hour. The reaction mixture was allowed to cool to room temperature, suspended in about 20 mL of ethyl acetate, and poured into about 100 g of ice. The resulting solution was neutralized with aqueous sodium bicarbonate, and the residue was extracted with ethyl acetate and separated. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.
  • Reference production example 5 In a water bath, 1.41 g of triethylamine was added dropwise to a mixture of 1.70 g of 2-bromopropiophenone, 2.06 g of 3,5-dichloro-2-pyridylacetic acid and 30 mL of acetonitrile, and the mixture was stirred at room temperature for 4 hours. I left still overnight. 30 mL of acetonitrile was added to the mixture, and 4.56 g of DBU was added dropwise under ice cooling. The mixture was stirred at room temperature for 1 hour. Thereafter, air was blown into the obtained mixture for 3 hours while stirring at room temperature.
  • Formulation Example 1 2.5 parts of any of the present pyridazine compounds (1) to (6), 1.25 parts of bixaphene, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 76.25 parts of xylene Each formulation is obtained by mixing.
  • Formulation Example 2 2.5 parts of any one of the pyridazine compounds (1) to (6), 1.25 parts of isopyrazam, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 76.25 parts of xylene Each formulation is obtained by mixing.
  • Formulation Example 3 2.5 parts of any one of the present pyridazine compounds (1) to (6), 1.25 parts of boscalid, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 76.25 parts of xylene Each formulation is obtained by mixing.
  • Formulation Example 4 2.5 parts of any one of the pyridazine compounds (1) to (6), 1.25 parts of fluopyram, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 76.25 parts of xylene Each formulation is obtained by mixing.
  • Formulation Example 5 2.5 parts of any of the present pyridazine compounds (1) to (6), 1.25 parts of floxapyroxide, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 76.25 xylene Each formulation is obtained by mixing the parts well.
  • Formulation Example 6 2.5 parts of any one of the pyridazine compounds (1) to (6), 1.25 parts of sedaxane, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 76.25 parts of xylene Each formulation is obtained by mixing.
  • Formulation Example 7 2.5 parts of any of the present pyridazine compounds (1) to (6), 1.25 parts of penflufen, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 76.25 parts of xylene Each formulation is obtained by mixing.
  • Formulation Example 8 2.5 parts of any one of the pyridazine compounds (1) to (6), 1.25 parts of flutolanil, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 76.25 parts of xylene Each formulation is obtained by mixing.
  • Formulation Example 9 2.5 parts of any one of the pyridazine compounds (1) to (6), 1.25 parts of mepronil, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 76.25 parts of xylene Each formulation is obtained by mixing.
  • Formulation Example 10 2.5 parts of any one of the pyridazine compounds (1) to (6), 1.25 parts of carboxin, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 76.25 parts of xylene. Each formulation is obtained by mixing well.
  • Formulation Example 12 2.5 parts of any of the present pyridazine compounds (1) to (6), 1.25 parts of pentiopyrad, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 76.25 parts of xylene Each formulation is obtained by mixing.
  • Formulation Example 13 2.5 parts of any one of the pyridazine compounds (1) to (6), 1.25 parts of furametopyl, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 76.25 parts of xylene Each formulation is obtained by mixing.
  • Formulation Example 14 2 parts of any of the pyridazine compounds (1) to (6), 8 parts of bixaphene, 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and 55 parts of water Each formulation is obtained by mixing and pulverizing by a wet pulverization method.
  • Formulation Example 15 2 parts of any of the pyridazine compounds (1) to (6), 8 parts of isopyrazam, 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and 55 parts of water Each formulation is obtained by mixing and pulverizing by a wet pulverization method.
  • Formulation Example 16 2 parts of any of the present pyridazine compounds (1) to (6), 8 parts of boscalid, 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and 55 parts of water Each formulation is obtained by mixing and pulverizing by a wet pulverization method.
  • Formulation Example 17 2 parts of any of the present pyridazine compounds (1) to (6), 8 parts of fluopyram, 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and 55 parts of water Each formulation is obtained by mixing and pulverizing by a wet pulverization method.
  • Formulation Example 18 2 parts of any one of the present pyridazine compounds (1) to (6), 8 parts of floxapyroxide, 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and water Each formulation is obtained by mixing 55 parts and pulverizing by a wet pulverization method.
  • Formulation Example 19 2 parts of any of the present pyridazine compounds (1) to (6), 8 parts of sedaxane, 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and 55 parts of water Each formulation is obtained by mixing and pulverizing by a wet pulverization method.
  • Formulation Example 20 2 parts of any of the present pyridazine compounds (1) to (6), 8 parts of penflufen, 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and 55 parts of water Each formulation is obtained by mixing and pulverizing by a wet pulverization method.
  • Formulation Example 21 2 parts of any of the present pyridazine compounds (1) to (6), 8 parts of flutolanil, 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and 55 parts of water Each formulation is obtained by mixing and pulverizing by a wet pulverization method.
  • Formulation Example 22 2 parts of any of the pyridazine compounds (1) to (6), 8 parts of mepronil, 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and 55 parts of water Each formulation is obtained by mixing and pulverizing by a wet pulverization method.
  • Formulation Example 23 2 parts of the pyridazine compounds (1) to (6), 8 parts of carboxin, 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and 55 parts of water Are mixed and finely pulverized by a wet pulverization method to obtain each preparation.
  • Formulation Example 24 2 parts of any of the pyridazine compounds (1) to (6), 8 parts of tifluzamide, 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and 55 parts of water Each formulation is obtained by mixing and pulverizing by a wet pulverization method.
  • Formulation Example 25 2 parts of any of the present pyridazine compounds (1) to (6), 8 parts of pentiopyrad, 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and 55 parts of water Each formulation is obtained by mixing and pulverizing by a wet pulverization method.
  • Formulation Example 26 2 parts of any of the present pyridazine compounds (1) to (6), 8 parts of furametopil, 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and 55 parts of water Each formulation is obtained by mixing and pulverizing by a wet pulverization method.
  • Formulation Example 27 5 parts of any of the pyridazine compounds (1) to (6), 10 parts of bixaphene, 1.5 parts of sorbitan trioleate and 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol are mixed and finely divided by a wet grinding method. Smash. To the obtained pulverized product, 45 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added, and 10 parts of propylene glycol is further added and stirred and mixed to obtain each preparation.
  • Formulation Example 28 5 parts of any one of the pyridazine compounds (1) to (6), 10 parts of isopyrazam, 1.5 parts of sorbitan trioleate and 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol are mixed and finely divided by a wet grinding method. Smash. To the obtained pulverized product, 45 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added, and 10 parts of propylene glycol is further added and stirred and mixed to obtain each preparation.
  • Formulation Example 29 5 parts of any one of the pyridazine compounds (1) to (6), 10 parts of boscalid, 1.5 parts of sorbitan trioleate and 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol are mixed and finely divided by a wet grinding method. Smash. To the obtained pulverized product, 45 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added, and 10 parts of propylene glycol is further added and stirred and mixed to obtain each preparation.
  • Formulation Example 30 5 parts of any one of the pyridazine compounds (1) to (6), 10 parts of fluopyram, 28.5 parts of an aqueous solution containing 1.5 parts of sorbitan trioleate and 2 parts of polyvinyl alcohol are mixed and finely divided by a wet grinding method. Smash. To the obtained pulverized product, 45 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added, and 10 parts of propylene glycol is further added and stirred and mixed to obtain each preparation.
  • Formulation Example 31 58.5 parts of any of the pyridazine compounds (1) to (6), 10 parts of floxapyroxad, 1.5 parts of sorbitan trioleate and 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol are mixed and wet-ground. Pulverize by the method. To the obtained pulverized product, 45 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added, and 10 parts of propylene glycol is further added and stirred and mixed to obtain each preparation.
  • Formulation Example 32 5 parts of any one of the pyridazine compounds (1) to (6), 10 parts of sedaxane, 1.5 parts of sorbitan trioleate and 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol are mixed and finely divided by a wet grinding method. Smash. To the obtained pulverized product, 45 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added, and 10 parts of propylene glycol is further added and stirred and mixed to obtain each preparation.
  • Formulation Example 33 5 parts of any one of the pyridazine compounds (1) to (6), 10 parts of penflufen, 1.5 parts of sorbitan trioleate and 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol are mixed and finely divided by a wet grinding method. Smash. To the obtained pulverized product, 45 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added, and 10 parts of propylene glycol is further added and stirred and mixed to obtain each preparation.
  • Formulation Example 34 5 parts of any one of the pyridazine compounds (1) to (6), 10 parts of flutolanil, 1.5 parts of sorbitan trioleate and 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol are mixed and finely divided by a wet pulverization method. Smash. To the obtained pulverized product, 45 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added, and 10 parts of propylene glycol is further added and stirred and mixed to obtain each preparation.
  • Formulation Example 35 5 parts of any one of the pyridazine compounds (1) to (6), 10 parts of mepronil, 1.5 parts of sorbitan trioleate and 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol are mixed and finely divided by a wet grinding method. Smash. To the obtained pulverized product, 45 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added, and 10 parts of propylene glycol is further added and stirred and mixed to obtain each preparation.
  • Formulation Example 36 58.5 parts of any one of the pyridazine compounds (1) to (6), 10 parts of carboxin, 1.5 parts of sorbitan trioleate and 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol are mixed and mixed by a wet grinding method. Finely pulverize. To the obtained pulverized product, 45 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added, and 10 parts of propylene glycol is further added and stirred and mixed to obtain each preparation.
  • Formulation Example 37 5 parts of any one of the pyridazine compounds (1) to (6), 10 parts of tifluzamide, 1.5 parts of sorbitan trioleate and 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol are mixed and finely divided by a wet grinding method. Smash. To the obtained pulverized product, 45 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added, and 10 parts of propylene glycol is further added and stirred and mixed to obtain each preparation.
  • Formulation Example 38 5 parts of any one of the pyridazine compounds (1) to (6), 10 parts of pentiopyrad, 1.5 parts of sorbitan trioleate and 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol are mixed and finely divided by a wet grinding method. Smash. To the obtained pulverized product, 45 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added, and 10 parts of propylene glycol is further added and stirred and mixed to obtain each preparation.
  • Formulation Example 39 5 parts of any one of the pyridazine compounds (1) to (6), 10 parts of furametopil, 1.5 parts of sorbitan trioleate and 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol are mixed and finely divided by a wet grinding method. Smash. To the obtained pulverized product, 45 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added, and 10 parts of propylene glycol is further added and stirred and mixed to obtain each preparation.
  • Formulation Example 40 1 part of any one of the pyridazine compounds (1) to (6), 4 parts of bixaphene, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 62 parts of kaolin clay are thoroughly mixed. After adding water and kneading well, each formulation is obtained by granulating and drying.
  • Formulation Example 41 1 part of any one of the pyridazine compounds (1) to (6), 4 parts of isopyrazam, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 62 parts of kaolin clay are thoroughly mixed. After adding water and kneading well, each formulation is obtained by granulating and drying.
  • Formulation Example 42 1 part of any of the present pyridazine compounds (1) to (6), 4 parts of boscalid, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 62 parts of kaolin clay are thoroughly mixed. After adding water and kneading well, each formulation is obtained by granulating and drying.
  • Formulation Example 43 1 part of any one of the present pyridazine compounds (1) to (6), 4 parts of fluopyram, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 62 parts of kaolin clay are thoroughly mixed. After adding water and kneading well, each formulation is obtained by granulating and drying.
  • Formulation Example 44 1 part of any one of the pyridazine compounds (1) to (6), 4 parts of floxapyroxide, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 62 parts of kaolin clay Each formulation is obtained by mixing, adding water, kneading well, and granulating and drying.
  • Formulation Example 45 1 part of any one of the pyridazine compounds (1) to (6), 4 parts of sedaxane, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 62 parts of kaolin clay are thoroughly mixed. After adding water and kneading well, each formulation is obtained by granulating and drying.
  • Formulation Example 46 1 part of any of the present pyridazine compounds (1) to (6), 4 parts of penflufen, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 62 parts of kaolin clay are thoroughly mixed. After adding water and kneading well, each formulation is obtained by granulating and drying.
  • Formulation Example 47 1 part of any one of the pyridazine compounds (1) to (6), 4 parts of flutolanil, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 62 parts of kaolin clay are thoroughly mixed. After adding water and kneading well, each formulation is obtained by granulating and drying.
  • Formulation Example 48 1 part of any one of the pyridazine compounds (1) to (6), 4 parts of mepronil, 1 part of synthetic silicon hydroxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 62 parts of kaolin clay are thoroughly mixed. After adding water and kneading well, each formulation is obtained by granulating and drying.
  • Formulation Example 49 1 part of any of the pyridazine compounds (1) to (6), 4 parts of carboxin, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 62 parts of kaolin clay are thoroughly pulverized and mixed. Each formulation is obtained by adding water and kneading well, followed by granulation drying.
  • Formulation Example 50 1 part of any one of the pyridazine compounds (1) to (6), 4 parts of tifluzamide, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 62 parts of kaolin clay are thoroughly mixed. After adding water and kneading well, each formulation is obtained by granulating and drying.
  • Formulation Example 51 1 part of any of the present pyridazine compounds (1) to (6), 4 parts of pentiopyrad, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 62 parts of kaolin clay are mixed well. After adding water and kneading well, each formulation is obtained by granulating and drying.
  • Formulation Example 52 1 part of any one of the present pyridazine compounds (1) to (6), 4 parts of furametopil, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 62 parts of kaolin clay are thoroughly mixed. After adding water and kneading well, each formulation is obtained by granulating and drying.
  • Formulation Example 53 12.5 parts of any one of the present pyridazine compounds (1) to (6), 37.5 parts of floxapyroxide, 3 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate and 45 parts of synthetic hydrous hydroxide Each formulation is obtained by grinding and mixing.
  • Formulation Example 54 A preparation is obtained by thoroughly pulverizing and mixing 3 parts of any of the present pyridazine compounds (1) to (6), 2 parts of isopyrazam, 85 parts of kaolin clay and 10 parts of talc.
  • Test example 1 A plastic pot was filled with soil, and wheat (cultivar; Apoge) was sown on the soil and grown in a greenhouse for 14 days.
  • Test example 2 Using a rotary seed processing machine (seed dresser, manufactured by Hans-Ulrich Hege GmbH), a test sample having a predetermined weight was applied to 10 g of wheat (cultivar: Shirogane) seeds naturally infected with spores of Microdochium nibale. 100 ⁇ L of the cyclohexanone solution containing the compound is smeared. One day after the treatment, the soil is packed in a plastic pot, seeds treated with the test compound are sown, and cultivated in a glass greenhouse for 20 days (this is referred to as a treatment zone). Thereafter, the presence or absence of red snow rot in seedlings sprouting from various offsprings is observed, and the incidence is determined by the following formula (2).

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

Abstract

L'invention concerne une composition de lutte contre les maladies des plantes, qui comprend un composé de pyridazine représenté par la formule (I) (dans laquelle R1 représente un atome de chlore, un atome de brome, un groupe cyano, un groupe méthyle ou un groupe méthoxy, R2 représente un atome de fluor ou un atome d'hydrogène, R3 représente un atome d'halogène et R4 représente un atome d'halogène, un groupe méthoxy ou un atome d'hydrogène) et un ou plusieurs types d'un composé de carboxamide, sélectionné(s) dans le groupe (A). Le groupe (A) comprend le bixafène, l'isopyrazam, le boscalide, le fluopyram, le fluxapyroxade, le sédaxane, le penflufène, le flutolanil, le mépronil, la carboxine, le thifluzamide, le penthiopyrade et le furametpyr.
PCT/JP2011/068199 2010-08-10 2011-08-09 Composition de lutte contre les maladies des plantes et utilisation de celle-ci Ceased WO2012020777A1 (fr)

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JP2010179302A JP2012036143A (ja) 2010-08-10 2010-08-10 植物病害防除組成物およびその用途
JP2010-179302 2010-08-10

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US9955691B2 (en) 2014-07-08 2018-05-01 Dow Agrosciences Llc Macrocyclic picolinamides as fungicides
US9974304B2 (en) 2013-12-26 2018-05-22 Dow Agrosciences Llc Use of macrocyclic picolinamides as fungicides
US10173971B2 (en) 2014-12-30 2019-01-08 Dow Agrosciences Llc Picolinamides with fungicidal activity
US10172358B2 (en) 2016-08-30 2019-01-08 Dow Agrosciences Llc Thiopicolinamide compounds with fungicidal activity
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US10173982B2 (en) 2016-08-30 2019-01-08 Dow Agrosciences Llc Picolinamides as fungicides
US10173981B2 (en) 2014-12-30 2019-01-08 Dow Agrosciences Llc Picolinamides as fungicides
US10182568B2 (en) 2014-12-30 2019-01-22 Dow Agrosciences Llc Use of picolinamide compounds as fungicides
US10188109B2 (en) 2014-12-30 2019-01-29 Dow Agrosciences Llc Picolinamide compounds with fungicidal activity
US10244754B2 (en) 2016-08-30 2019-04-02 Dow Agrosciences Llc Picolinamide N-oxide compounds with fungicidal activity
US10246417B2 (en) 2017-01-05 2019-04-02 Dow Agrosciences Llc Picolinamides as fungicides
US10334852B2 (en) 2016-08-30 2019-07-02 Dow Agrosciences Llc Pyrido-1,3-oxazine-2,4-dione compounds with fungicidal activity
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US11155520B2 (en) 2018-03-08 2021-10-26 Dow Agrosciences Llc Picolinamides as fungicides
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US11206828B2 (en) 2017-05-02 2021-12-28 Corteva Agriscience Llc Synergistic mixtures for fungal controls in cereals
US11639334B2 (en) 2018-10-15 2023-05-02 Corteva Agriscience Llc Methods for synthesis of oxypicolinamides
US11771085B2 (en) 2017-05-02 2023-10-03 Corteva Agriscience Llc Synergistic mixtures for fungal control in cereals
US12281076B2 (en) 2019-10-18 2025-04-22 Corteva Agriscience Llc Process for synthesis of picolinamides

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US10172354B2 (en) 2012-12-28 2019-01-08 Dow Agrosciences Llc Synergistic fungicidal mixtures for fungal control in cereals
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US10334852B2 (en) 2016-08-30 2019-07-02 Dow Agrosciences Llc Pyrido-1,3-oxazine-2,4-dione compounds with fungicidal activity
US10244754B2 (en) 2016-08-30 2019-04-02 Dow Agrosciences Llc Picolinamide N-oxide compounds with fungicidal activity
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US10246417B2 (en) 2017-01-05 2019-04-02 Dow Agrosciences Llc Picolinamides as fungicides
US11206828B2 (en) 2017-05-02 2021-12-28 Corteva Agriscience Llc Synergistic mixtures for fungal controls in cereals
US11191269B2 (en) 2017-05-02 2021-12-07 Dow Agrosciences Llc Use of an acyclic picolinamide compound as a fungicide for fungal diseases on turfgrasses
US11771085B2 (en) 2017-05-02 2023-10-03 Corteva Agriscience Llc Synergistic mixtures for fungal control in cereals
US11155520B2 (en) 2018-03-08 2021-10-26 Dow Agrosciences Llc Picolinamides as fungicides
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US11639334B2 (en) 2018-10-15 2023-05-02 Corteva Agriscience Llc Methods for synthesis of oxypicolinamides
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