WO2012020779A1 - 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
WO2012020779A1
WO2012020779A1 PCT/JP2011/068201 JP2011068201W WO2012020779A1 WO 2012020779 A1 WO2012020779 A1 WO 2012020779A1 JP 2011068201 W JP2011068201 W JP 2011068201W WO 2012020779 A1 WO2012020779 A1 WO 2012020779A1
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present
compound
parts
carboxamide compound
pyridazine
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PCT/JP2011/068201
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English (en)
Japanese (ja)
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雄一 松崎
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住友化学株式会社
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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
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles

Definitions

  • the present invention relates to a plant disease control composition and its use.
  • Patent Documents 1, 2, and 3 Conventionally, many compounds have been developed and put into practical use for controlling plant diseases (see, for example, Patent Documents 1, 2, and 3).
  • 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 carboxamide compound represented by the following formula (I) and a pyridazine compound represented by the following formula (II).
  • the composition has an excellent control effect against plant diseases. That is, the present invention is as follows. [1] Formula (I) [Where, R 1 represents a hydrogen atom or a methyl group, R 2 represents a methyl group, a difluoromethyl group or a trifluoromethyl group.
  • a carboxamide compound represented by Formula (II) [Where, A 1 represents a chlorine atom, a bromine atom, a cyano group, a methyl group or a methoxy group, A 2 represents a fluorine atom or a hydrogen atom, A 3 represents a halogen atom, A 4 represents a halogen atom, a methoxy group or a hydrogen atom. ]
  • a carboxamide compound represented by Formula (II) [Where, A 1 represents a chlorine atom, a bromine atom, a cyano group, a methyl group or a methoxy group, A 2 represents a fluorine atom or a hydrogen atom, A 3 represents a halogen atom, A 4 represents a halogen atom, a methoxy group or a hydrogen atom.
  • the plant disease control method including the process of processing the effective amount with the pyridazine compound shown by the plant or the soil which grows a plant.
  • the method for controlling plant diseases according to [3], wherein the weight ratio of the carboxamide compound to the pyridazine compound is carboxamide compound / pyridazine compound 0.1 / 1 to 10/1.
  • 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) [Wherein, R 1 and R 2 represent the same meaning as described above. ]
  • a carboxamide compound (hereinafter referred to as the present carboxamide compound) represented by formula (II): [Where, A 1 represents a chlorine atom, a bromine atom, a cyano group, a methyl group or a methoxy group, A 2 represents a fluorine atom or a hydrogen atom, A 3 represents a halogen atom, A 4 represents a halogen atom, a methoxy group or a hydrogen atom. ] And a pyridazine compound (hereinafter referred to as the present pyridazine compound).
  • the present carboxamide compound is a compound described in, for example, International Publication No. 86/02641 pamphlet and International Publication No. 92/12970 pamphlet, and can be produced by the methods described therein.
  • present carboxamide compound examples include the following.
  • a carboxamide compound represented by the formula (1) hereinafter referred to as the present carboxamide compound (1)
  • a carboxamide compound represented by the formula (2) hereinafter referred to as the present carboxamide compound (2)
  • a carboxamide compound represented by the formula (3) hereinafter referred to as the present carboxamide compound (3)
  • a carboxamide compound represented by the formula (4) hereinafter referred to as the present carboxamide compound (4)
  • a carboxamide compound represented by the formula (5) hereinafter referred to as the present carboxamide compound (5).
  • examples of the halogen atom represented by each of A 3 and A 4 include a chlorine atom, a bromine atom, and a fluorine atom.
  • Examples of the present pyridazine compound include the following pyridazine compounds.
  • a 1 is a chlorine atom
  • a 2 is a fluorine atom
  • a 3 is a chlorine atom
  • a 4 is a chlorine atom
  • a 1 is a bromine atom
  • a 2 is a fluorine atom
  • a 3 is a chlorine atom
  • a 4 is a chlorine atom (hereinafter referred to as the present pyridazine compound (2)).
  • a 1 is a cyano group
  • a 2 is a fluorine atom
  • a 3 is a chlorine atom
  • a 4 is a chlorine atom
  • a 1 is a methyl group
  • a 2 is a fluorine atom
  • a 3 is a chlorine atom
  • a 4 is a chlorine atom (hereinafter referred to as the present pyridazine compound (4)).
  • a 1 is a methoxy group
  • a 2 is a fluorine atom
  • a 3 is a chlorine atom
  • a 4 is a chlorine atom
  • a 1 is a chlorine atom
  • a 2 is a hydrogen atom
  • a 3 is a chlorine atom
  • a 4 is a chlorine atom (hereinafter referred to as the present pyridazine compound (6)).
  • a pyridazine compound in which A 1 is a chlorine atom, a bromine atom, a methyl group or a methoxy group in formula (II) is produced, for example, by the method described in International Publication No. 2007/066601 pamphlet. be able to.
  • the compound (II-2) in which A 1 is a cyano group in the formula (II) is, for example, the compound (A) in the formula (II) in which A 1 is a bromine atom. It can be produced by reacting II-1) with copper cyanide. [Wherein, A 2 , A 3 and A 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 (II-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 (II-2) can be isolated.
  • Compound (II-2) can be further purified by chromatography, recrystallization and the like.
  • the compound (II-4) in which A 1 is a methyl group in the formula (II) is the compound (II-) in which the A 1 is a chlorine atom in the formula (II) among the pyridazine compounds. 3) is converted to formula (III) [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, A 2 , A 3 and A 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 (II-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, whereby the compound (II-4) is simply obtained. Can be separated.
  • the isolated compound (II-4) can be further purified by chromatography, recrystallization and the like.
  • the composition of the present invention may be a mixture of the present carboxamide compound and the present pyridazine compound, but the composition of the present invention is usually prepared by mixing the present carboxamide compound, the present pyridazine compound and an inert carrier and, if necessary, surface active. 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 composition of the present invention contains the present carboxamide compound and the present pyridazine 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 carboxamide compound and the pyridazine compound by the above-described methods, and then diluting with water as necessary to mix 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 rust disease (Puccinia strictiformis, P. graminis, P. recondita), naked smut (Ustilago tritici), and magusa. Smut (Tilletia caries), leaf blight (Mycosphaerella graminicola), blight (Stagonospora nodorum), yellow spot (Pyrenophora tritici-repentis); Etc.
  • rust disease Pierinia strictiformis, P. graminis, P. recondita
  • naked smut Ustilago tritici
  • magusa Smut (Tilletia caries), leaf blight (Mycosphaerella graminicola), blight (Stagonospora nodorum), yellow spot (Pyrenophora tritici-repentis); Etc.
  • composition comprising the present carboxamide compound (1) and the present pyridazine compound (1); A composition comprising the present carboxamide compound (1) and the present pyridazine compound (2); A composition comprising the present carboxamide compound (1) and the present pyridazine compound (3); A composition comprising the present carboxamide compound (1) and the present pyridazine compound (4); A composition comprising the present carboxamide compound (1) and the present pyridazine compound (5); A composition comprising the present carboxamide compound (1) and the present pyridazine compound (6);
  • a composition comprising the present carboxamide compound (1) and the present pyridazine compound (1) in a weight ratio of the present carboxamide compound (1) / the present pyridazine compound (1) 0.1 / 1 to 10/1;
  • a composition comprising the present carboxamide compound (1) and the present pyridazine compound (2) in a weight ratio of the present carboxamide compound (1) / the present pyridazine compound (2) 0.1 / 1 to 10/1;
  • a composition comprising the present carboxamide compound (1) and the present pyridazine compound (3) in a weight ratio of the present carboxamide compound (1) / the present pyridazine compound (3) 0.1 / 1 to 10/1;
  • a composition comprising the present carboxamide compound (1) and the present pyridazine compound (4) in a weight ratio of the present carboxamide compound (1) / the present pyridazine compound (4) 0.1 / 1 to 10/1;
  • a composition comprising the present carboxamide compound (2) and the present pyridazine compound (1) in a weight ratio of the present carboxamide compound (2) / the present pyridazine compound (1) 0.1 / 1 to 10/1;
  • a composition comprising the present carboxamide compound (2) and the present pyridazine compound (2) in a weight ratio of the present carboxamide compound (2) / the present pyridazine compound (2) 0.1 / 1 to 10/1;
  • a composition comprising the present carboxamide compound (2) and the present pyridazine compound (3) in a weight ratio of the present carboxamide compound (2) / the present pyridazine compound (3) 0.1 / 1 to 10/1;
  • a composition comprising the present carboxamide compound (2) and the present pyridazine compound (4) in a weight ratio of the present carboxamide compound (2) / the present pyridazine compound (4) 0.1 / 1 to 10/1;
  • a composition comprising the present carboxamide compound (3) and the present pyridazine compound (1) in a weight ratio of the present carboxamide compound (3) / the present pyridazine compound (1) 0.1 / 1 to 10/1;
  • a composition comprising the present carboxamide compound (3) and the present pyridazine compound (2) in a weight ratio of the present carboxamide compound (3) / the present pyridazine compound (2) 0.1 / 1 to 10/1;
  • a composition comprising the present carboxamide compound (3) and the present pyridazine compound (3) in a weight ratio of the present carboxamide compound (3) / the present pyridazine compound (3) 0.1 / 1 to 10/1;
  • a composition comprising the present carboxamide compound (3) and the present pyridazine compound (4) in a weight ratio of the present carboxamide compound (3) / the present pyridazine compound (4) 0.1 / 1 to 10/1;
  • a composition comprising the present carboxamide compound (4) and the present pyridazine compound (1) in a weight ratio of the present carboxamide compound (4) / the present pyridazine compound (1) 0.1 / 1 to 10/1;
  • a composition comprising the present carboxamide compound (4) and the present pyridazine compound (2) in a weight ratio of the present carboxamide compound (4) / the present pyridazine compound (2) 0.1 / 1 to 10/1;
  • a composition comprising the present carboxamide compound (4) and the present pyridazine compound (3) in a weight ratio of the present carboxamide compound (4) / the present pyridazine compound (3) 0.1 / 1 to 10/1;
  • a composition comprising the present carboxamide compound (4) and the present pyridazine compound (4) in a weight ratio of the present carboxamide compound (4) / the present pyridazine compound (4) 0.1 / 1 to 10/1;
  • a composition comprising the present carboxamide compound (5) and the present pyridazine compound (1) in a weight ratio of the present carboxamide compound (5) / the present pyridazine compound (1) 0.1 / 1 to 10/1;
  • a composition comprising the present carboxamide compound (5) and the present pyridazine compound (2) in a weight ratio of the present carboxamide compound (5) / the present pyridazine compound (2) 0.1 / 1 to 10/1;
  • a composition comprising the present carboxamide compound (5) and the present pyridazine compound (3) in a weight ratio of the present carboxamide compound (5) / the present pyridazine compound (3) 0.1 / 1 to 10/1;
  • a composition comprising the present carboxamide compound (5) and the present pyridazine compound (4) in a weight ratio of the present carboxamide compound (5) / the present pyridazine compound (4) 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 carboxamide compound and the present pyridazine compound on the plant or the soil where the plant is cultivated.
  • Such 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 present carboxamide compound and the present pyridazine compound may be treated separately in the same period on the plant or soil where the plant is cultivated. Is processed as
  • examples of the method for treating the present carboxamide compound and the present pyridazine 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.
  • Such root treatment includes, for example, a method of immersing the whole plant or root in a chemical solution containing the present carboxamide compound and the present pyridazine compound, and a solid preparation containing the present carboxamide compound, the present pyridazine 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.
  • Such 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.
  • 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 carboxamide compound and the present pyridazine 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 the total amount of the present carboxamide compound and the present pyridazine compound, usually 1 to 500 g, preferably 2 per 1000 m 2. ⁇ 200 g, more preferably 10 ⁇ 100 g.
  • the amount of the present carboxamide compound and the present pyridazine compound in the seed treatment is the total amount of the present carboxamide compound and the present pyridazine 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 carboxamide compound and the present pyridazine compound is generally 0.0005 to 2% by weight, preferably 0.005 to 1% by weight as the total concentration of the present carboxamide compound and the present pyridazine 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 the present carboxamide compound (1), 1.25 parts of any of the present pyridazine compounds (1) to (6), 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate and xylene 76 Each formulation is obtained by mixing well 25 parts.
  • Formulation Example 2 2.5 parts of the present carboxamide compound (2), 1.25 parts of any of the present pyridazine compounds (1) to (6), 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate and xylene 76 Each formulation is obtained by mixing well 25 parts.
  • Formulation Example 3 2.5 parts of the present carboxamide compound (3), 1.25 parts of any of the present pyridazine compounds (1) to (6), 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate and xylene 76 Each formulation is obtained by mixing well 25 parts.
  • Formulation Example 4 2.5 parts of the present carboxamide compound (4), 1.25 parts of any of the present pyridazine compounds (1) to (6), 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate, and xylene 76 Each formulation is obtained by mixing well 25 parts.
  • Formulation Example 5 2.5 parts of the present carboxamide compound (5), 1.25 parts of any of the present pyridazine compounds (1) to (6), 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate, and xylene 76 Each formulation is obtained by mixing well 25 parts.
  • Formulation Example 6 2 parts of the present carboxamide compound (1), 8 parts of any of the present pyridazine compounds (1) to (6), 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 pulverized by a wet pulverization method to obtain each preparation.
  • Formulation Example 7 2 parts of the present carboxamide compound (2), 8 parts of any of the present pyridazine compounds (1) to (6), 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 pulverized by a wet pulverization method to obtain each preparation.
  • Formulation Example 8 2 parts of the present carboxamide compound (3), 8 parts of any of the present pyridazine compounds (1) to (6), and 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 pulverized by a wet pulverization method to obtain each preparation.
  • Formulation Example 9 2 parts of the present carboxamide compound (4), 8 parts of any of the present pyridazine compounds (1) to (6), and 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 pulverized by a wet pulverization method to obtain each preparation.
  • Formulation Example 10 2 parts of the present carboxamide compound (5), 8 parts of any of the present pyridazine compounds (1) to (6), 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 pulverized by a wet pulverization method to obtain each preparation.
  • Formulation Example 11 5 parts of the present carboxamide compound (1), 10 parts of any of the present pyridazine compounds (1) to (6), 1.5 parts of sorbitan trioleate and 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol are mixed, Finely pulverize by wet pulverization 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 12 5 parts of the present carboxamide compound (2), 10 parts of any of the present pyridazine compounds (1) to (6), 1.5 parts of sorbitan trioleate and 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol are mixed, Finely pulverize by wet pulverization 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 13 5 parts of the present carboxamide compound (3), 10 parts of any of the present pyridazine compounds (1) to (6), 1.5 parts of sorbitan trioleate and 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol, Finely pulverize by wet pulverization. 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 14 5 parts of the present carboxamide compound (4), 10 parts of any of the present pyridazine compounds (1) to (6), 1.5 parts of sorbitan trioleate and 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol are mixed, Finely pulverize by wet pulverization 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 15 5 parts of the present carboxamide compound (5), 10 parts of any of the present pyridazine compounds (1) to (6), 1.5 parts of sorbitan trioleate and 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol, Finely pulverize by wet pulverization 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 16 1 part of the present carboxamide compound (1), 4 parts of any of the present pyridazine compounds (1) to (6), 1 part of synthetic silicon hydroxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 62 parts of kaolin clay Each formulation is obtained by pulverizing and mixing well, adding water, kneading well, and granulating and drying.
  • Formulation Example 17 1 part of the present carboxamide compound (2), 4 parts of any of the present pyridazine compounds (1) to (6), 1 part of synthetic silicon hydroxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 62 parts of kaolin clay Each formulation is obtained by pulverizing and mixing well, adding water, kneading well, and granulating and drying.
  • Formulation Example 18 1 part of the present carboxamide compound (3), 4 parts of any of the present pyridazine compounds (1) to (6), 1 part of synthetic silicon hydroxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 62 parts of kaolin clay Each formulation is obtained by pulverizing and mixing well, adding water, kneading well, and granulating and drying.
  • Formulation Example 19 1 part of the present carboxamide compound (4), 4 parts of any of the present pyridazine compounds (1) to (6), 1 part of synthetic silicon hydroxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 62 parts of kaolin clay Each formulation is obtained by pulverizing and mixing well, adding water, kneading well, and granulating and drying.
  • Formulation Example 20 1 part of the present carboxamide compound (5), 4 parts of any of the present pyridazine compounds (1) to (6), 1 part of synthetic silicon hydroxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 62 parts of kaolin clay Each formulation is obtained by thoroughly pulverizing and mixing, adding water, kneading well, and granulating and drying.
  • Formulation Example 21 12.5 parts of the present carboxamide compound (1), 37.5 parts of any of the present pyridazine compounds (1) to (6), 3 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and 45 parts of synthetic silicon hydroxide Each formulation is obtained by pulverizing and mixing well.
  • Formulation Example 22 12.5 parts of the present carboxamide compound (2), 37.5 parts of any of the present pyridazine compounds (1) to (6), 3 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and 45 parts of synthetic silicon hydroxide Each formulation is obtained by pulverizing and mixing well.
  • Formulation Example 23 12.5 parts of the present carboxamide compound (3), 37.5 parts of any of the present pyridazine compounds (1) to (6), 3 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and 45 parts of synthetic silicon hydroxide Each formulation is obtained by pulverizing and mixing well.
  • Formulation Example 24 12.5 parts of the present carboxamide compound (4), 37.5 parts of any of the present pyridazine compounds (1) to (6), 3 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and 45 parts of synthetic silicon hydroxide Each formulation is obtained by pulverizing and mixing well.
  • Formulation Example 25 12.5 parts of the present carboxamide compound (5), 37.5 parts of any of the present pyridazine compounds (1) to (6), 3 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and 45 parts of synthetic silicon hydroxide Each formulation is obtained by pulverizing and mixing well.
  • Formulation Example 26 Each formulation is obtained by thoroughly grinding and mixing 3 parts of the present carboxamide compound (1), 2 parts of any of the present pyridazine compounds (1) to (6), 85 parts of kaolin clay and 10 parts of talc.
  • Formulation Example 27 Each formulation is obtained by thoroughly pulverizing and mixing 3 parts of the present carboxamide compound (2), 2 parts of any of the present pyridazine compounds (1) to (6), 85 parts of kaolin clay and 10 parts of talc.
  • Formulation Example 28 Each formulation is obtained by thoroughly pulverizing and mixing 3 parts of the present carboxamide compound (3), 2 parts of any of the present pyridazine compounds (1) to (6), 85 parts of kaolin clay and 10 parts of talc.
  • Formulation Example 29 Each formulation is obtained by thoroughly pulverizing and mixing 3 parts of the present carboxamide compound (4), 2 parts of any of the present pyridazine compounds (1) to (6), 85 parts of kaolin clay and 10 parts of talc.
  • Formulation Example 30 Each formulation is obtained by thoroughly pulverizing and mixing 3 parts of the present carboxamide compound (5), 2 parts of any of the present pyridazine compounds (1) to (6), 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.

Landscapes

  • 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

L'invention concerne une composition de lutte contre les maladies des plantes, qui comprend un composé de carboxamide représenté par la formule (I) (dans laquelle R1 représente un atome d'hydrogène ou un groupe méthyle, et R2 représente un groupe méthyle, un groupe difluorométhyle ou un groupe trifluorométhyle) et un composé de pyridazine représenté par la formule (II) (dans laquelle A1 représente un atome de chlore, un atome de brome, un groupe cyano, un groupe méthyle ou un groupe méthoxy, A2 représente un atome de fluor ou un atome d'hydrogène, A3 représente un atome d'halogène et A4 représente un atome d'halogène, un groupe méthoxy ou un atome d'hydrogène).
PCT/JP2011/068201 2010-08-10 2011-08-09 Composition de lutte contre les maladies des plantes et utilisation de celle-ci WO2012020779A1 (fr)

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JP2010-179305 2010-08-10

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1986002641A1 (fr) * 1984-10-29 1986-05-09 Sumitomo Chemical Company, Limited Derives de pyrazolecarboxamide, procede de preparation et bactericides les contenant en tant qu'ingredients efficaces
JPH06505252A (ja) * 1991-01-28 1994-06-16 モンサント・カンパニー ３−ジフルオロメチルピラゾールカルボキサミド殺菌剤
WO2007066601A1 (fr) * 2005-12-07 2007-06-14 Sumitomo Chemical Company, Limited Compose de pyridazine et son emploi

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1986002641A1 (fr) * 1984-10-29 1986-05-09 Sumitomo Chemical Company, Limited Derives de pyrazolecarboxamide, procede de preparation et bactericides les contenant en tant qu'ingredients efficaces
JPH06505252A (ja) * 1991-01-28 1994-06-16 モンサント・カンパニー ３−ジフルオロメチルピラゾールカルボキサミド殺菌剤
WO2007066601A1 (fr) * 2005-12-07 2007-06-14 Sumitomo Chemical Company, Limited Compose de pyridazine et son emploi

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