WO2012020779A1 - Plant disease control composition and application for same - Google Patents

Plant disease control composition and application for same 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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Prior art keywords
present
compound
parts
carboxamide compound
pyridazine
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PCT/JP2011/068201
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French (fr)
Japanese (ja)
Inventor
雄一 松崎
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住友化学株式会社
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Publication of WO2012020779A1 publication Critical patent/WO2012020779A1/en

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—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.

Abstract

The present invention provides a plant disease control composition that includes a carboxamide compound indicated by formula (I) (wherein R1 indicates a hydrogen atom or a methyl group, and R2 indicates a methyl group, a difluoromethyl group, or a trifluoromethyl group) and a pyridazine compound indicated by formula (II) (wherein A1 indicates a chlorine atom, a bromine atom, a cyano group, a methyl group, or a methoxy group, A2 indicates a fluorine atom or a hydrogen atom, A3 indicates a halogen atom, and A4 indicates a halogen atom, a methoxy group, or a hydrogen atom.)　

Description

植物病害防除組成物およびその用途Plant disease control composition and use thereof
　本発明は、植物病害防除組成物およびその用途に関する。 The present invention relates to a plant disease control composition and its use.
　従来、植物病害を防除するために多くの化合物が開発され、実用に供されている（例えば、特許文献１、２及び３参照。）。 Conventionally, many compounds have been developed and put into practical use for controlling plant diseases (see, for example, Patent Documents 1, 2, and 3).
国際公開第８６／０２６４１号パンフレットInternational Publication No. 86/02641 Pamphlet 国際公開第９２／１２９７０号パンフレットInternational Publication No. 92/12970 Pamphlet 国際公開第２００７／０６６６０１号パンフレットInternational Publication No. 2007/066601 Pamphlet
　本発明は、植物病害に対して優れた防除効力を有する組成物を提供することを課題とする。 An object of the present invention is to provide a composition having an excellent control effect against plant diseases.
　本発明は、下記式（Ｉ）で示されるカルボキサミド化合物と、下記式（ＩＩ）で示されるピリダジン化合物とを含有する植物病害防除組成物等を提供する。当該組成物は、植物病害に対して優れた防除効力を有する。
　すなわち、本発明は以下の通りである。
［１］　式（Ｉ）
Figure JPOXMLDOC01-appb-I000005
〔式中、
Ｒ１は水素原子又はメチル基を表し、
Ｒ２はメチル基、ジフルオロメチル基又はトリフルオロメチル基を表す。〕
で示されるカルボキサミド化合物と、
式（ＩＩ）
Figure JPOXMLDOC01-appb-I000006
〔式中、
Ａ1は塩素原子、臭素原子、シアノ基、メチル基又はメトキシ基を表し、
Ａ2はフッ素原子又は水素原子を表し、
Ａ3はハロゲン原子を表し、
Ａ4はハロゲン原子、メトキシ基又は水素原子を表す。〕
で示されるピリダジン化合物とを含有する植物病害防除組成物。
［２］　カルボキサミド化合物とピリダジン化合物との重量比が、カルボキサミド化合物／ピリダジン化合物＝０．１／１～１０／１である［１］記載の植物病害防除組成物。
［３］　式（Ｉ）
Figure JPOXMLDOC01-appb-I000007
〔式中、
Ｒ１は水素原子又はメチル基を表し、
Ｒ２はメチル基、ジフルオロメチル基又はトリフルオロメチル基を表す。〕
で示されるカルボキサミド化合物と、
式（ＩＩ）
Figure JPOXMLDOC01-appb-I000008
〔式中、
Ａ1は塩素原子、臭素原子、シアノ基、メチル基又はメトキシ基を表し、
Ａ2はフッ素原子又は水素原子を表し、
Ａ3はハロゲン原子を表し、
Ａ4はハロゲン原子、メトキシ基又は水素原子を表す。〕
で示されるピリダジン化合物との有効量を、植物又は植物を栽培する土壌に処理する工程を含む植物病害防除方法。
［４］　カルボキサミド化合物とピリダジン化合物との重量比が、カルボキサミド化合物／ピリダジン化合物＝０．１／１～１０／１である［３］記載の植物病害防除方法。
［５］　植物又は植物を栽培する土壌が、コムギ又はコムギを栽培する土壌である［３］又は［４］記載の植物病害防除方法。 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)
Figure JPOXMLDOC01-appb-I000005
[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)
Figure JPOXMLDOC01-appb-I000006
[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 composition containing the pyridazine compound shown by these.
[2] The plant disease control composition according to [1], wherein the weight ratio of the carboxamide compound to the pyridazine compound is carboxamide compound / pyridazine compound = 0.1 / 1 to 10/1.
[3] Formula (I)
Figure JPOXMLDOC01-appb-I000007
[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)
Figure JPOXMLDOC01-appb-I000008
[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.
[4] 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.
[5] 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.
　本発明により、植物病害を防除することができる。 According to the present invention, plant diseases can be controlled.
　本発明の植物病害防除組成物（以下、本発明組成物と記す。）は、式（Ｉ）
Figure JPOXMLDOC01-appb-I000009
〔式中、Ｒ１及びＲ２は前記と同じ意味を表す。〕
で示されるカルボキサミド化合物（以下、本カルボキサミド化合物と記す。）と、式（ＩＩ）
Figure JPOXMLDOC01-appb-I000010
〔式中、
Ａ1は塩素原子、臭素原子、シアノ基、メチル基又はメトキシ基を表し、
Ａ2はフッ素原子又は水素原子を表し、
Ａ3はハロゲン原子を表し、
Ａ4はハロゲン原子、メトキシ基又は水素原子を表す。〕
で示されるピリダジン化合物（以下、本ピリダジン化合物と記す。）とを含有する。 The plant disease control composition of the present invention (hereinafter referred to as the present composition) has the formula (I)
Figure JPOXMLDOC01-appb-I000009
[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):
Figure JPOXMLDOC01-appb-I000010
[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).
　本カルボキサミド化合物は、例えば国際公開第８６／０２６４１号パンフレット及び国際公開第９２／１２９７０号パンフレットに記載された化合物であり、これらに記載の方法で製造することができる。 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.
　本カルボキサミド化合物の具体例としては、以下のものが挙げられる。
式（１）で示されるカルボキサミド化合物（以下、本カルボキサミド化合物（１）と記す。）；
Figure JPOXMLDOC01-appb-I000011
式（２）で示されるカルボキサミド化合物（以下、本カルボキサミド化合物（２）と記す。）；
Figure JPOXMLDOC01-appb-I000012
式（３）で示されるカルボキサミド化合物（以下、本カルボキサミド化合物（３）と記す。）；
Figure JPOXMLDOC01-appb-I000013
式（４）で示されるカルボキサミド化合物（以下、本カルボキサミド化合物（４）と記す。）；
Figure JPOXMLDOC01-appb-I000014
及び、
式（５）で示されるカルボキサミド化合物（以下、本カルボキサミド化合物（５）と記す。）。
Figure JPOXMLDOC01-appb-I000015
Specific examples of the present carboxamide compound include the following.
A carboxamide compound represented by the formula (1) (hereinafter referred to as the present carboxamide compound (1));
Figure JPOXMLDOC01-appb-I000011
A carboxamide compound represented by the formula (2) (hereinafter referred to as the present carboxamide compound (2));
Figure JPOXMLDOC01-appb-I000012
A carboxamide compound represented by the formula (3) (hereinafter referred to as the present carboxamide compound (3));
Figure JPOXMLDOC01-appb-I000013
A carboxamide compound represented by the formula (4) (hereinafter referred to as the present carboxamide compound (4));
Figure JPOXMLDOC01-appb-I000014
as well as,
A carboxamide compound represented by the formula (5) (hereinafter referred to as the present carboxamide compound (5)).
Figure JPOXMLDOC01-appb-I000015
　本発明組成物に用いる本ピリダジン化合物について説明する。
　式（ＩＩ）において、Ａ３及びＡ４のそれぞれで示される、ハロゲン原子としては、例えば、塩素原子、臭素原子及びフッ素原子が挙げられる。 The pyridazine compound used in the composition of the present invention will be described.
In the formula (II), 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.
　本ピリダジン化合物の態様としては、例えば以下のピリダジン化合物があげられる。 Examples of the present pyridazine compound include the following pyridazine compounds.
式（ＩＩ）において、Ａ１が塩素原子又はメトキシ基であるピリダジン化合物；
式（ＩＩ）において、Ａ１が塩素原子であるピリダジン化合物；
式（ＩＩ）において、Ａ１がメチル基であるピリダジン化合物；
式（ＩＩ）において、Ａ２がフッ素原子であるピリダジン化合物；
式（ＩＩ）において、Ａ２が水素原子であるピリダジン化合物；
式（ＩＩ）において、Ａ３が塩素原子又はフッ素原子であるピリダジン化合物；
式（ＩＩ）において、Ａ３が塩素原子であるピリダジン化合物；
式（ＩＩ）において、Ａ４が塩素原子、フッ素原子又は水素原子であるピリダジン化合物；
式（ＩＩ）において、Ａ４が塩素原子であるピリダジン化合物；
式（ＩＩ）において、Ａ３が塩素原子又はフッ素原子であり、Ａ４が塩素原子であるピリダジン化合物；
式（ＩＩ）において、Ａ３が塩素原子であり、Ａ４が塩素原子であるピリダジン化合物；
式（ＩＩ）において、Ａ１が塩素原子又はメトキシ基であり、Ａ３が塩素原子又はフッ素原子であり、Ａ４が塩素原子であるピリダジン化合物；
式（ＩＩ）において、Ａ１が塩素原子であり、Ａ３が塩素原子又はフッ素原子であり、Ａ４が塩素原子であるピリダジン化合物；
式（ＩＩ）において、Ａ１が塩素原子又はメトキシ基であり、Ａ３が塩素原子であり、Ａ４が塩素原子であるピリダジン化合物；
式（ＩＩ）において、Ａ１が塩素原子であり、Ａ３が塩素原子であり、Ａ４が塩素原子であるピリダジン化合物。 A pyridazine compound represented by formula (II), wherein A 1 is a chlorine atom or a methoxy group;
A pyridazine compound represented by formula (II), wherein A 1 is a chlorine atom;
A pyridazine compound represented by formula (II), wherein A 1 is a methyl group;
A pyridazine compound represented by formula (II), wherein A 2 is a fluorine atom;
A pyridazine compound represented by formula (II), wherein A 2 is a hydrogen atom;
A pyridazine compound represented by formula (II), wherein A 3 is a chlorine atom or a fluorine atom;
A pyridazine compound represented by formula (II), wherein A 3 is a chlorine atom;
A pyridazine compound represented by formula (II), wherein A 4 is a chlorine atom, a fluorine atom or a hydrogen atom;
A pyridazine compound represented by formula (II), wherein A 4 is a chlorine atom;
A pyridazine compound represented by formula (II), wherein A 3 is a chlorine atom or a fluorine atom, and A 4 is a chlorine atom;
A pyridazine compound represented by formula (II), wherein A 3 is a chlorine atom and A 4 is a chlorine atom;
A pyridazine compound represented by the formula (II), wherein A 1 is a chlorine atom or a methoxy group, A 3 is a chlorine atom or a fluorine atom, and A 4 is a chlorine atom;
A pyridazine compound represented by the formula (II), wherein A 1 is a chlorine atom, A 3 is a chlorine atom or a fluorine atom, and A 4 is a chlorine atom;
A pyridazine compound represented by the formula (II), wherein A 1 is a chlorine atom or a methoxy group, A 3 is a chlorine atom, and A 4 is a chlorine atom;
A pyridazine compound represented by the formula (II), wherein A 1 is a chlorine atom, A 3 is a chlorine atom, and A 4 is a chlorine atom.
　次に、本ピリダジン化合物の具体例を示す。
式（ＩＩ）において、Ａ１が塩素原子であり、Ａ２がフッ素原子であり、Ａ３が塩素原子であり、Ａ４が塩素原子であるピリダジン化合物（以下、本ピリダジン化合物（１）と記す。）；
式（ＩＩ）において、Ａ１が臭素原子であり、Ａ２がフッ素原子であり、Ａ３が塩素原子であり、Ａ４が塩素原子であるピリダジン化合物（以下、本ピリダジン化合物（２）と記す。）；
式（ＩＩ）において、Ａ１がシアノ基であり、Ａ２がフッ素原子であり、Ａ３が塩素原子であり、Ａ４が塩素原子であるピリダジン化合物（以下、本ピリダジン化合物（３）と記す。）；
式（ＩＩ）において、Ａ１がメチル基であり、Ａ２がフッ素原子であり、Ａ３が塩素原子であり、Ａ４が塩素原子であるピリダジン化合物（以下、本ピリダジン化合物（４）と記す。）；
式（ＩＩ）において、Ａ１がメトキシ基であり、Ａ２がフッ素原子であり、Ａ３が塩素原子であり、Ａ４が塩素原子であるピリダジン化合物（以下、本ピリダジン化合物（５）と記す。）；
式（ＩＩ）において、Ａ１が塩素原子であり、Ａ２が水素原子であり、Ａ３が塩素原子であり、Ａ４が塩素原子であるピリダジン化合物（以下、本ピリダジン化合物（６）と記す。）。 Next, specific examples of the pyridazine compound will be shown.
In formula (II), A 1 is a chlorine atom, A 2 is a fluorine atom, A 3 is a chlorine atom, and A 4 is a chlorine atom (hereinafter referred to as the present pyridazine compound (1)). .);
In formula (II), A 1 is a bromine atom, A 2 is a fluorine atom, A 3 is a chlorine atom, and A 4 is a chlorine atom (hereinafter referred to as the present pyridazine compound (2)). .);
In formula (II), A 1 is a cyano group, A 2 is a fluorine atom, A 3 is a chlorine atom, and A 4 is a chlorine atom (hereinafter referred to as the present pyridazine compound (3)). .);
In formula (II), A 1 is a methyl group, A 2 is a fluorine atom, A 3 is a chlorine atom, and A 4 is a chlorine atom (hereinafter referred to as the present pyridazine compound (4)). .);
In formula (II), A 1 is a methoxy group, A 2 is a fluorine atom, A 3 is a chlorine atom, and A 4 is a chlorine atom (hereinafter referred to as the present pyridazine compound (5)). .);
In formula (II), A 1 is a chlorine atom, A 2 is a hydrogen atom, A 3 is a chlorine atom, and A 4 is a chlorine atom (hereinafter referred to as the present pyridazine compound (6)). .)
　次に、本ピリダジン化合物の製造法について説明する。
　本ピリダジン化合物のうち、式（ＩＩ）において、Ａ１が塩素原子、臭素原子、メチル基又はメトキシ基であるピリダジン化合物は、例えば、国際公開第２００７／０６６６０１号パンフレットに記載された方法により製造することができる。 Next, the manufacturing method of this pyridazine compound is demonstrated.
Among the pyridazine compounds, 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.
　本ピリダジン化合物のうち、式（ＩＩ）において、Ａ１がシアノ基である化合物（ＩＩ－２）は、例えば、本ピリダジン化合物のうち、式（ＩＩ）において、Ａ１が臭素原子である化合物（ＩＩ－１）をシアン化銅と反応させることにより製造することができる。
Figure JPOXMLDOC01-appb-I000016
〔式中、Ａ２、Ａ３、Ａ４は前記と同じ意味を表す。〕
　該反応は、通常溶媒の存在下で行われる。
　反応に用いられる溶媒としては、例えば、Ｎ，Ｎ－ジメチルアセトアミドなどの非プロトン性極性溶媒が挙げられる。
　該反応に用いられるシアン化銅の量は、化合物（ＩＩ－１）１モルに対して、通常１～１．５モルの割合である。
　該反応の反応温度は通常１２０～１８０℃の範囲であり、反応時間は通常１～２４時間の範囲である。
　反応終了後は、例えば、反応混合物を水及び有機溶媒と混合してからろ過し、ろ液を分液し、得られた有機層をさらに水洗後、乾燥、濃縮する等の操作を行うことにより、化合物（ＩＩ－２）を単離することができる。化合物（ＩＩ－２）はクロマトグラフィー、再結晶等によりさらに精製することもできる。 Among the pyridazine compounds, 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.
Figure JPOXMLDOC01-appb-I000016
[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.
After completion of the reaction, for example, 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.
　本ピリダジン化合物のうち、式（ＩＩ）において、Ａ１がメチル基である化合物
（ＩＩ－４）は、本ピリダジン化合物のうち、式（ＩＩ）において、Ａ１が塩素原子である化合物（ＩＩ－３）を、式（III）
Figure JPOXMLDOC01-appb-I000017
〔式中、Ｘは臭素原子又は塩素原子を表す。〕
で示されるグリニャール試薬と鉄触媒の存在下に反応させることにより製造することができる。
Figure JPOXMLDOC01-appb-I000018
〔式中、Ａ２、Ａ３、Ａ４は前記と同じ意味を表す。〕
　該反応は、通常溶媒の存在下で行われる。
　反応に用いられる溶媒としては、例えば、テトラヒドロフラン、ジエチルエーテル及びＮ－メチルピロリドン、並びにそれらの混合溶媒が挙げられる。反応溶媒がテトラヒドロフランとＮ－メチルピロリドンとの混合物である場合、テトラヒドロフランとＮ－メチルピロリドンとの混合比は、容量比で通常３０：１から３：１の範囲である。
　該反応に用いられる鉄触媒としては、例えば、アセチルアセトン鉄（III）及び塩化鉄（III）が挙げられる。用いられる鉄触媒の量は、化合物（ＩＩ－３）１モルに対して、通常０．０１～０．３モルの割合である。
　該反応の反応温度は通常－２０℃～３０℃の範囲であり、反応時間は通常０．１～６時間の範囲である。
　反応終了後は、例えば、反応混合物を塩酸と混合してから有機溶媒抽出し、得られた有機層を水洗後、乾燥、濃縮する等の操作を行うことにより、化合物（ＩＩ－４）を単離することができる。単離された化合物（ＩＩ－４）はクロマトグラフィー、再結晶等によりさらに精製することもできる。 Among the pyridazine compounds, 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)
Figure JPOXMLDOC01-appb-I000017
[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.
Figure JPOXMLDOC01-appb-I000018
[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. When 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. to 30 ° C., and the reaction time is usually in the range of 0.1 to 6 hours.
After completion of the reaction, for example, 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.
　本発明組成物における、本カルボキサミド化合物と本ピリダジン化合物との重量比は、通常、本カルボキサミド化合物／本ピリダジン化合物＝０．０１／１～５００／１、好ましくは０．１／１～１０／１である。 The weight ratio of the present carboxamide compound to the present pyridazine compound in the composition of the present invention is usually the present carboxamide compound / the present pyridazine compound = 0.01 / 1 to 500/1, preferably 0.1 / 1 to 10/1. It is.
　本発明組成物は、本カルボキサミド化合物と本ピリダジン化合物との混合物そのものでもよいが、本発明組成物は、通常、本カルボキサミド化合物、本ピリダジン化合物及び不活性担体を混合し、必要に応じて界面活性剤やその他の製剤用補助剤を添加して、油剤、乳剤、フロアブル剤、水和剤、顆粒水和剤、粉剤、粒剤等に製剤化されている。かかる製剤は、そのまま又はその他の不活性成分を添加して植物病害防除剤として使用することができる。
　本発明組成物には、本カルボキサミド化合物及び本ピリダジン化合物が合計で、通常０．１～９９重量％、好ましくは０．２～９０重量％、より好ましくは１～８０重量％含有される。 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.
　製剤化の際に用いられる固体担体としては、例えばカオリンクレー、アッタパルジャイトクレー、ベントナイト、モンモリロナイト、酸性白土、パイロフィライト、タルク、珪藻土、方解石等の鉱物、トウモロコシ穂軸粉、クルミ殻粉等の天然有機物、尿素等の合成有機物、炭酸カルシウム、硫酸アンモニウム等の塩類、合成含水酸化珪素等の合成無機物等からなる微粉末あるいは粒状物等が挙げられ、液体担体としては、例えばキシレン、アルキルベンゼン、メチルナフタレン等の芳香族炭化水素類、２－プロパノール、エチレングリコール、プロピレングリコール、エチレングリコールモノエチルエーテル等のアルコール類、アセトン、シクロヘキサノン、イソホロン等のケトン類、ダイズ油、綿実油等の植物油、石油系脂肪族炭化水素類、エステル類、ジメチルスルホキシド、アセトニトリル及び水が挙げられる。
　界面活性剤としては、例えばアルキル硫酸エステル塩、アルキルアリールスルホン酸塩、ジアルキルスルホコハク酸塩、ポリオキシエチレンアルキルアリールエーテルリン酸エステル塩、リグニンスルホン酸塩、ナフタレンスルホネートホルムアルデヒド重縮合物等の陰イオン界面活性剤、及びポリオキシエチレンアルキルアリールエーテル、ポリオキシエチレンアルキルポリオキシプロピレンブロックコポリマー、ソルビタン脂肪酸エステル等の非イオン界面活性剤、及びアルキルトリメチルアンモニウム塩等の陽イオン界面活性剤が挙げられる。
　その他の製剤用補助剤としては、例えばポリビニルアルコール、ポリビニルピロリドン等の水溶性高分子、アラビアガム、アルギン酸及びその塩、ＣＭＣ（カルボキシメチルセルロ－ス）、キサンタンガム等の多糖類、アルミニウムマグネシウムシリケート、アルミナゾル等の無機物、防腐剤、着色剤及びＰＡＰ（酸性リン酸イソプロピル）、ＢＨＴ等の安定化剤が挙げられる。 Examples of 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., and 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.
Examples of 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.
Other 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.
　本発明組成物はまた、本カルボキサミド化合物と本ピリダジン化合物とを各々前記した方法により製剤化した上で、必要に応じて水で希釈してそれぞれの製剤又はそれらの希釈液を混合することにより調製することもできる。 The 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
　本発明組成物は、植物病害から植物を保護するために用いることができる。 The composition of the present invention can be used to protect plants from plant diseases.
　本発明組成物が防除効力を有する植物病害としては、例えば次のものが挙げられる。
　イネの病害：いもち病（Ｍａｇｎａｐｏｒｔｈｅ　ｇｒｉｓｅａ）、ごま葉枯病（Ｃｏｃｈｌｉｏｂｏｌｕｓ　ｍｉｙａｂｅａｎｕｓ）、紋枯病（Ｒｈｉｚｏｃｔｏｎｉａ　ｓｏｌａｎｉ）、馬鹿苗病（Ｇｉｂｂｅｒｅｌｌａ　ｆｕｊｉｋｕｒｏｉ）。
　コムギの病害：うどんこ病（Ｅｒｙｓｉｐｈｅ　ｇｒａｍｉｎｉｓ）、赤かび病（Ｆｕｓａｒｉｕｍ　ｇｒａｍｉｎｅａｒｕｍ、Ｆ．　ａｖｅｎａｃｅｒｕｍ、Ｆ．　ｃｕｌｍｏｒｕｍ、Ｍｉｃｒｏｄｏｃｈｉｕｍ　ｎｉｖａｌｅ）、さび病（Ｐｕｃｃｉｎｉａ　ｓｔｒｉｉｆｏｒｍｉｓ、Ｐ．　ｇｒａｍｉｎｉｓ、Ｐ．　ｒｅｃｏｎｄｉｔａ）、紅色雪腐病（Ｍｉｃｒｏｎｅｃｔｒｉｅｌｌａ　ｎｉｖａｌｅ）、雪腐小粒菌核病（Ｔｙｐｈｕｌａ　ｓｐ．）、裸黒穂病（Ｕｓｔｉｌａｇｏ　ｔｒｉｔｉｃｉ）、なまぐさ黒穂病（Ｔｉｌｌｅｔｉａ　ｃａｒｉｅｓ）、眼紋病（Ｐｓｅｕｄｏｃｅｒｃｏｓｐｏｒｅｌｌａ　ｈｅｒｐｏｔｒｉｃｈｏｉｄｅｓ）、葉枯病（Ｍｙｃｏｓｐｈａｅｒｅｌｌａ　ｇｒａｍｉｎｉｃｏｌａ）、ふ枯病（Ｓｔａｇｏｎｏｓｐｏｒａ　ｎｏｄｏｒｕｍ）、黄斑病（Ｐｙｒｅｎｏｐｈｏｒａ　ｔｒｉｔｉｃｉ－ｒｅｐｅｎｔｉｓ）。
　オオムギの病害：うどんこ病（Ｅｒｙｓｉｐｈｅ　ｇｒａｍｉｎｉｓ）、赤かび病（Ｆｕｓａｒｉｕｍ　ｇｒａｍｉｎｅａｒｕｍ、Ｆ．　ａｖｅｎａｃｅｒｕｍ、Ｆ．　ｃｕｌｍｏｒｕｍ、Ｍｉｃｒｏｄｏｃｈｉｕｍ　ｎｉｖａｌｅ）、さび病（Ｐｕｃｃｉｎｉａ　ｓｔｒｉｉｆｏｒｍｉｓ、Ｐ．ｇｒａｍｉｎｉｓ、Ｐ．ｈｏｒｄｅｉ）、裸黒穂病（Ｕｓｔｉｌａｇｏ　ｎｕｄａ）、雲形病（Ｒｈｙｎｃｈｏｓｐｏｒｉｕｍ　ｓｅｃａｌｉｓ）、網斑病（Ｐｙｒｅｎｏｐｈｏｒａ　ｔｅｒｅｓ）、斑点病（Ｃｏｃｈｌｉｏｂｏｌｕｓ　ｓａｔｉｖｕｓ）、斑葉病（Ｐｙｒｅｎｏｐｈｏｒａ　ｇｒａｍｉｎｅａ）、リゾクトニア属菌による苗立枯れ病（Ｒｈｉｚｏｃｔｏｎｉａ　ｓｏｌａｎｉ）。
　トウモロコシの病害：黒穂病（Ｕｓｔｉｌａｇｏ　ｍａｙｄｉｓ）、ごま葉枯病（Ｃｏｃｈｌｉｏｂｏｌｕｓ　ｈｅｔｅｒｏｓｔｒｏｐｈｕｓ）、ひょう紋病（Ｇｌｏｅｏｃｅｒｃｏｓｐｏｒａ　ｓｏｒｇｈｉ）、南方さび病（Ｐｕｃｃｉｎｉａ　ｐｏｌｙｓｏｒａ）、グレイリーフスポット病（Ｃｅｒｃｏｓｐｏｒａ　ｚｅａｅ－ｍａｙｄｉｓ）、リゾクトニア属菌による苗立枯れ病（Ｒｈｉｚｏｃｔｏｎｉａ　ｓｏｌａｎｉ）。 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. (Microlectriella nivale), Snow rot microspora nuclear disease (Typhula sp.), Bare smut (Ustilago tritici), Tuna scab (Pseudocercosporella herposis), Blight (Stagonospo) a nodorum), Kimadarabyo (Pyrenophora tritici-repentis).
Diseases of barley: powdery mildew (Erysiphe graminis), red mold disease (Fusarium gramaminerum, F. avenacerum, F. culmorum, Microdochium nitrifle, black punishment) Ustilago nuda), cloud disease (Rhynchosporium secalis), reticular disease (Pyrenophora teres), spot disease (Cochliobolus sativus), leafy leaf disease (Pyrenophora graminea), and 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.
　カンキツ類の病害：黒点病（Ｄｉａｐｏｒｔｈｅ　ｃｉｔｒｉ）、そうか病（Ｅｌｓｉｎｏｅ　ｆａｗｃｅｔｔｉ）、果実腐敗病（Ｐｅｎｉｃｉｌｌｉｕｍ　ｄｉｇｉｔａｔｕｍ，　Ｐ．　ｉｔａｌｉｃｕｍ）、フィトフトラ病（Ｐｈｙｔｏｐｈｔｈｏｒａ　ｐａｒａｓｉｔｉｃａ、Ｐｈｙｔｏｐｈｔｈｏｒａ　ｃｉｔｒｏｐｈｔｈｏｒａ）。
　リンゴの病害：モニリア病（Ｍｏｎｉｌｉｎｉａ　ｍａｌｉ）、腐らん病（Ｖａｌｓａ　ｃｅｒａｔｏｓｐｅｒｍａ）、うどんこ病（Ｐｏｄｏｓｐｈａｅｒａ　ｌｅｕｃｏｔｒｉｃｈａ）、斑点落葉病（Ａｌｔｅｒｎａｒｉａ　ａｌｔｅｒｎａｔａ　ａｐｐｌｅ　ｐａｔｈｏｔｙｐｅ）、黒星病（Ｖｅｎｔｕｒｉａ　ｉｎａｅｑｕａｌｉｓ）、炭そ病（Ｃｏｌｌｅｔｏｔｒｉｃｈｕｍ　ａｃｕｔａｔｕｍ）、疫病（Ｐｈｙｔｏｐｈｔｈｏｒａ　ｃａｃｔｏｒｕｍ）。
　ナシの病害：黒星病（Ｖｅｎｔｕｒｉａ　ｎａｓｈｉｃｏｌａ，　Ｖ．　ｐｉｒｉｎａ）、黒斑病（Ａｌｔｅｒｎａｒｉａ　ａｌｔｅｒｎａｔａ　Ｊａｐａｎｅｓｅ　ｐｅａｒ　ｐａｔｈｏｔｙｐｅ）、赤星病（Ｇｙｍｎｏｓｐｏｒａｎｇｉｕｍ　ｈａｒａｅａｎｕｍ）、疫病（Ｐｈｙｔｏｐｈｔｈｏｒａ　ｃａｃｔｏｒｕｍ）；
　モモの病害：灰星病（Ｍｏｎｉｌｉｎｉａ　ｆｒｕｃｔｉｃｏｌａ）、黒星病（Ｃｌａｄｏｓｐｏｒｉｕｍ　ｃａｒｐｏｐｈｉｌｕｍ）、フォモプシス腐敗病（Ｐｈｏｍｏｐｓｉｓ　ｓｐ．）。
　ブドウの病害：黒とう病（Ｅｌｓｉｎｏｅ　ａｍｐｅｌｉｎａ）、晩腐病（Ｇｌｏｍｅｒｅｌｌａ　ｃｉｎｇｕｌａｔａ）、うどんこ病（Ｕｎｃｉｎｕｌａ　ｎｅｃａｔｏｒ）、さび病（Ｐｈａｋｏｐｓｏｒａ　ａｍｐｅｌｏｐｓｉｄｉｓ）、ブラックロット病（Ｇｕｉｇｎａｒｄｉａ　ｂｉｄｗｅｌｌｉｉ）、べと病（Ｐｌａｓｍｏｐａｒａ　ｖｉｔｉｃｏｌａ）。
　カキの病害：炭そ病（Ｇｌｏｅｏｓｐｏｒｉｕｍ　ｋａｋｉ）、落葉病（Ｃｅｒｃｏｓｐｏｒａ　ｋａｋｉ，　Ｍｙｃｏｓｐｈａｅｒｅｌｌａ　ｎａｗａｅ）。
　ウリ類の病害：炭そ病（Ｃｏｌｌｅｔｏｔｒｉｃｈｕｍ　ｌａｇｅｎａｒｉｕｍ）、うどんこ病（Ｓｐｈａｅｒｏｔｈｅｃａ　ｆｕｌｉｇｉｎｅａ）、つる枯病（Ｍｙｃｏｓｐｈａｅｒｅｌｌａ　ｍｅｌｏｎｉｓ）、つる割病（Ｆｕｓａｒｉｕｍ　ｏｘｙｓｐｏｒｕｍ）、べと病（Ｐｓｅｕｄｏｐｅｒｏｎｏｓｐｏｒａ　ｃｕｂｅｎｓｉｓ）、疫病（Ｐｈｙｔｏｐｈｔｈｏｒａ　ｓｐ．）、苗立枯病（Ｐｙｔｈｉｕｍ　ｓｐ．）；
　トマトの病害：輪紋病（Ａｌｔｅｒｎａｒｉａ　ｓｏｌａｎｉ）、葉かび病（Ｃｌａｄｏｓｐｏｒｉｕｍ　ｆｕｌｖｕｍ）、疫病（Ｐｈｙｔｏｐｈｔｈｏｒａ　ｉｎｆｅｓｔａｎｓ）。
　ナスの病害：褐紋病（Ｐｈｏｍｏｐｓｉｓ　ｖｅｘａｎｓ）、うどんこ病（Ｅｒｙｓｉｐｈｅ　ｃｉｃｈｏｒａｃｅａｒｕｍ）。
　アブラナ科野菜の病害：黒斑病（Ａｌｔｅｒｎａｒｉａ　ｊａｐｏｎｉｃａ）、白斑病（Ｃｅｒｃｏｓｐｏｒｅｌｌａ　ｂｒａｓｓｉｃａｅ）、根こぶ病（Ｐｌａｓｍｏｄｉｏｐｈｏｒａ　ｂｒａｓｓｉｃａｅ）、べと病（Ｐｅｒｏｎｏｓｐｏｒａ　ｐａｒａｓｉｔｉｃａ）。
　ネギの病害：さび病（Ｐｕｃｃｉｎｉａ　ａｌｌｉｉ）、べと病（Ｐｅｒｏｎｏｓｐｏｒａ　ｄｅｓｔｒｕｃｔｏｒ）。 Diseases of citrus: Black spot disease (Diaporthe citri), common scab (Elsinoe fawceti), fruit rot (Penicillium digitatum, P. italicum), Phytophthora paraphysitic or Phytophthora or Phytophthora parathitosis.
Diseases of apples: Monilia mary, rot (Valsa ceratosperma), powdery mildew (Podospataera leukotrica), spotted leaf disease (Alternaria altanatal pest disease) , Phytophthora catarum.
Pear diseases: black spot disease (Venturia nashicola, V. pirina), black spot disease (Alternaria alternata Japan pareopathy), red star disease (Gymnosporangium haraeumum), disease
Peach diseases: Monilinia fracticola, black scab (Cladosporium carpophilum), Phomopsis spoilage (Phomopsis sp.).
Grape diseases: black scab (Elsinoe ampelina), late rot (Glomerella cinulata), powdery mildew (Uncinula apelopidais), black rot (Gikonivaladi) .
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).
Diseases of eggplant: brown spot disease (Phomopsis vexans), powdery mildew (Erysiphe cichoacearum).
Diseases of cruciferous vegetables: black spot disease (Alternaria japonica), white spot disease (Cercosporella brassicae), clubroot (Plasmodiophora brassicae), downy mildew (Peronospora parasitica).
Diseases of leek: rust (Puccinia allii), downy mildew (Peronospora destructor).
　ダイズの病害：紫斑病（Ｃｅｒｃｏｓｐｏｒａ　ｋｉｋｕｃｈｉｉ）、黒とう病（Ｅｌｓｉｎｏｅ　ｇｌｙｃｉｎｅｓ）、黒点病（Ｄｉａｐｏｒｔｈｅ　ｐｈａｓｅｏｌｏｒｕｍ　ｖａｒ．　ｓｏｊａｅ）、褐紋病（Ｓｅｐｔｏｒｉａ　ｇｌｙｃｉｎｅｓ）、斑点病（Ｃｅｒｃｏｓｐｏｒａ　ｓｏｊｉｎａ）、さび病（Ｐｈａｋｏｐｓｏｒａ　ｐａｃｈｙｒｈｉｚｉ）、茎疫病（Ｐｈｙｔｏｐｈｔｈｏｒａ　ｓｏｊａｅ）、リゾクトニア属菌による苗立枯れ病（Ｒｈｉｚｏｃｔｏｎｉａ　ｓｏｌａｎｉ）褐色輪紋病（Ｃｏｒｙｎｅｓｐｏｒａ　ｃａｓｉｉｃｏｌａ）、菌核病（Ｓｃｌｅｒｏｔｉｎｉａ　ｓｃｌｅｒｏｔｉｏｒｕｍ）。
　インゲンの病害：炭そ病（Ｃｏｌｌｅｔｏｔｒｉｃｈｕｍ　ｌｉｎｄｅｍｔｈｉａｎｕｍ）。
　ラッカセイの病害：黒渋病（Ｃｅｒｃｏｓｐｏｒａ　ｐｅｒｓｏｎａｔａ）、褐斑病（Ｃｅｒｃｏｓｐｏｒａ　ａｒａｃｈｉｄｉｃｏｌａ）、白絹病（Ｓｃｌｅｒｏｔｉｕｍ　ｒｏｌｆｓｉｉ）。
　エンドウの病害：うどんこ病（Ｅｒｙｓｉｐｈｅ　ｐｉｓｉ）。
　ジャガイモの病害：夏疫病（Ａｌｔｅｒｎａｒｉａ　ｓｏｌａｎｉ）、疫病（Ｐｈｙｔｏｐｈｔｈｏｒａ　ｉｎｆｅｓｔａｎｓ）、緋色腐敗病（Ｐｈｙｔｏｐｈｔｈｏｒａ　ｅｒｙｔｈｒｏｓｅｐｔｉｃａ）、粉状そうか病（Ｓｐｏｎｇｏｓｐｏｒａ　ｓｕｂｔｅｒｒａｎｅａｎ　ｆ．　ｓｐ．　ｓｕｂｔｅｒｒａｎｅａ）。
　イチゴの病害：うどんこ病（Ｓｐｈａｅｒｏｔｈｅｃａ　ｈｕｍｕｌｉ）、炭そ病（Ｇｌｏｍｅｒｅｌｌａ　ｃｉｎｇｕｌａｔａ）。
　チャの病害：網もち病（Ｅｘｏｂａｓｉｄｉｕｍ　ｒｅｔｉｃｕｌａｔｕｍ）、白星病（Ｅｌｓｉｎｏｅ　ｌｅｕｃｏｓｐｉｌａ）、輪斑病（Ｐｅｓｔａｌｏｔｉｏｐｓｉｓ　ｓｐ．）、炭そ病（Ｃｏｌｌｅｔｏｔｒｉｃｈｕｍ　ｔｈｅａｅ－ｓｉｎｅｎｓｉｓ）。
　タバコの病害：赤星病（Ａｌｔｅｒｎａｒｉａ　ｌｏｎｇｉｐｅｓ）、うどんこ病（Ｅｒｙｓｉｐｈｅ　ｃｉｃｈｏｒａｃｅａｒｕｍ）、炭そ病（Ｃｏｌｌｅｔｏｔｒｉｃｈｕｍ　ｔａｂａｃｕｍ）、べと病（Ｐｅｒｏｎｏｓｐｏｒａ　ｔａｂａｃｉｎａ）、疫病（Ｐｈｙｔｏｐｈｔｈｏｒａ　ｎｉｃｏｔｉａｎａｅ）。
　ナタネの病害：菌核病（Ｓｃｌｅｒｏｔｉｎｉａ　ｓｃｌｅｒｏｔｉｏｒｕｍ）、リゾクトニア属菌による苗立枯れ病（Ｒｈｉｚｏｃｔｏｎｉａ　ｓｏｌａｎｉ）。
　ワタの病害：リゾクトニア属菌による苗立枯れ病（Ｒｈｉｚｏｃｔｏｎｉａ　ｓｏｌａｎｉ）。
　テンサイの病害：褐斑病（Ｃｅｒｃｏｓｐｏｒａ　ｂｅｔｉｃｏｌａ）、葉腐病（Ｔｈａｎａｔｅｐｈｏｒｕｓ　ｃｕｃｕｍｅｒｉｓ）、根腐病（Ｔｈａｎａｔｅｐｈｏｒｕｓ　ｃｕｃｕｍｅｒｉｓ）、黒根病（Ａｐｈａｎｏｍｙｃｅｓ　ｃｏｃｈｌｉｏｉｄｅｓ）。
　バラの病害：黒星病（Ｄｉｐｌｏｃａｒｐｏｎ　ｒｏｓａｅ）、うどんこ病（Ｓｐｈａｅｒｏｔｈｅｃａ　ｐａｎｎｏｓａ）、べと病（Ｐｅｒｏｎｏｓｐｏｒａ　ｓｐａｒｓａ）。
　キクおよびキク科野菜の病害：べと病（Ｂｒｅｍｉａ　ｌａｃｔｕｃａｅ）、褐斑病（Ｓｅｐｔｏｒｉａ　ｃｈｒｙｓａｎｔｈｅｍｉ－ｉｎｄｉｃｉ）、白さび病（Ｐｕｃｃｉｎｉａ　ｈｏｒｉａｎａ）。
　種々の作物の病害：ピシウム属菌によって引き起こされる病害（Ｐｙｔｈｉｕｍ　ａｐｈａｎｉｄｅｒｍａｔｕｍ，　Ｐｙｔｈｉｕｍ　ｄｅｂａｒｉａｎｕｍ，　Ｐｙｔｈｉｕｍ　ｇｒａｍｉｎｉｃｏｌａ，　Ｐｙｔｈｉｕｍ　ｉｒｒｅｇｕｌａｒｅ，　Ｐｙｔｈｉｕｍ　ｕｌｔｉｍｕｍ）、灰色かび病（Ｂｏｔｒｙｔｉｓ　ｃｉｎｅｒｅａ）、菌核病（Ｓｃｌｅｒｏｔｉｎｉａ　ｓｃｌｅｒｏｔｉｏｒｕｍ）。
　ダイコンの病害：黒斑病（Ａｌｔｅｒｎａｒｉａ　ｂｒａｓｓｉｃｉｃｏｌａ）。
　シバの病害：ダラースポット病（Ｓｃｌｅｒｏｔｉｎｉａ　ｈｏｍｅｏｃａｒｐａ）、ブラウンパッチ病およびラージパッチ病（Ｒｈｉｚｏｃｔｏｎｉａ　ｓｏｌａｎｉ）。
　バナナの病害：シガトカ病（Ｍｙｃｏｓｐｈａｅｒｅｌｌａ　ｆｉｊｉｅｎｓｉｓ、Ｍｙｃｏｓｐｈａｅｒｅｌｌａ　ｍｕｓｉｃｏｌａ）。
　ヒマワリの病害：べと病（Ｐｌａｓｍｏｐａｒａ　ｈａｌｓｔｅｄｉｉ）。
　Ａｓｐｅｒｇｉｌｌｕｓ属、Ｐｅｎｉｃｉｌｌｉｕｍ属、Ｆｕｓａｒｉｕｍ属、Ｇｉｂｂｅｒｅｌｌａ属、Ｔｒｉｃｏｄｅｒｍａ属、Ｔｈｉｅｌａｖｉｏｐｓｉｓ属、Ｒｈｉｚｏｐｕｓ属、Ｍｕｃｏｒ属、Ｃｏｒｔｉｃｉｕｍ属、Ｐｈｏｍａ属、Ｒｈｉｚｏｃｔｏｎｉａ属、およびＤｉｐｌｏｄｉａ属菌等によって引き起こされる、各種作物の種子病害または生育初期の病害。
　Ｐｏｌｙｍｉｘａ属またはＯｌｐｉｄｉｕｍ属等によって媒介される各種作物のウイルス病。 Diseases of 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. (Phythium aphanidermatum, Pythium debarianum, Pythium graminicola, Pythium irregulari, Pythium ultimatum), Gray mold disease (Botritris rot)
Radish disease: Alternaria brassicicola.
Diseases of buckwheat: Dollar spot disease (Sclerotinia homeocarpa), Brown patch disease and Large patch disease (Rhizotonia solani).
Banana disease: Sigatoka disease (Mycosphaerella fijiensis, Mycosphaerella musicola).
Sunflower disease: downy mildew (Plasmopara halstedii).
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.
　本発明組成物を使用できる植物としては、例えば次のものが挙げられる。
　農作物；トウモロコシ、イネ、コムギ、オオムギ、ライムギ、エンバク、ソルガム、ワタ、ダイズ、ピーナッツ、ソバ、テンサイ、ナタネ、ヒマワリ、サトウキビ、タバコ等、
　野菜；ナス科野菜（ナス、トマト、ピーマン、トウガラシ、ジャガイモ等）、ウリ科野菜（キュウリ、カボチャ、ズッキーニ、スイカ、メロン、スカッシュ等）、アブラナ科野菜（ダイコン、カブ、セイヨウワサビ、コールラビ、ハクサイ、キャベツ、カラシナ、ブロッコリー、カリフラワー等）、キク科野菜（ゴボウ、シュンギク、アーティチョーク、レタス等）、ユリ科野菜（ネギ、タマネギ、ニンニク、アスパラガス）、セリ科野菜（ニンジン、パセリ、セロリ、アメリカボウフウ等）、アカザ科野菜（ホウレンソウ、フダンソウ等）、シソ科野菜（シソ、ミント、バジル等）、イチゴ、サツマイモ、ヤマノイモ、サトイモ等、
　花卉、
　観葉植物、
　シバ、
　果樹；仁果類（リンゴ、セイヨウナシ、ニホンナシ、カリン、マルメロ等）、核果類（モモ、スモモ、ネクタリン、ウメ、オウトウ、アンズ、プルーン等）、カンキツ類（ウンシュウミカン、オレンジ、レモン、ライム、グレープフルーツ等）、堅果類（クリ、クルミ、ハシバミ、アーモンド、ピスタチオ、カシューナッツ、マカダミアナッツ等）、液果類（ブルーベリー、クランベリー、ブラックベリー、ラズベリー等）、ブドウ、カキ、オリーブ、ビワ、バナナ、コーヒー、ナツメヤシ、ココヤシ等、
　果樹以外の樹；チャ、クワ、花木、街路樹（トネリコ、カバノキ、ハナミズキ、ユーカリ、イチョウ、ライラック、カエデ、カシ、ポプラ、ハナズオウ、フウ、プラタナス、ケヤキ、クロベ、モミノキ、ツガ、ネズ、マツ、トウヒ、イチイ）等。 As a plant which can use this invention composition, the following are mentioned, for example.
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.
Bridegroom,
Foliage plant,
Shiva,
Fruit trees; pears (apples, pears, Japanese pears, quince, quince, etc.), nuclear fruits (peaches, plums, nectarines, ume, sweet cherry, apricots, prunes, etc.), citrus (satsuma mandarin, orange, lemon, lime, grapefruit) ), Nuts (chestnut, walnut, hazel, almond, pistachio, cashew nut, macadamia nut, etc.), berries (blueberry, cranberry, blackberry, raspberry, etc.), grape, oyster, olive, loquat, banana, coffee, Date palm, coconut palm, 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.
　前記した植物とは、遺伝子組換え技術により耐性を付与された植物であってもよい。 The above-mentioned plant may be a plant imparted with resistance by genetic recombination technology.
　上記のうち、特にコムギに発生する植物病害に対して高い防除効果が期待される。
　また、これらの作物に発生する植物病害のうち、特に高い効力が期待されるコムギの病害としては、さび病（Ｐｕｃｃｉｎｉａ　ｓｔｒｉｉｆｏｒｍｉｓ、Ｐ．　ｇｒａｍｉｎｉｓ、Ｐ．　ｒｅｃｏｎｄｉｔａ）、裸黒穂病（Ｕｓｔｉｌａｇｏ　ｔｒｉｔｉｃｉ）、なまぐさ黒穂病（Ｔｉｌｌｅｔｉａ　ｃａｒｉｅｓ）、葉枯病（Ｍｙｃｏｓｐｈａｅｒｅｌｌａ　ｇｒａｍｉｎｉｃｏｌａ）、ふ枯病（Ｓｔａｇｏｎｏｓｐｏｒａ　ｎｏｄｏｒｕｍ）、黄斑病（Ｐｙｒｅｎｏｐｈｏｒａ　ｔｒｉｔｉｃｉ－ｒｅｐｅｎｔｉｓ）；
等が挙げられる。 Of these, a high control effect is expected especially against plant diseases occurring in wheat.
Among the plant diseases that occur in these crops, 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.
　本発明組成物の態様としては、例えば以下のものが挙げられる。
本カルボキサミド化合物（１）と本ピリダジン化合物（１）とを含有する組成物；
本カルボキサミド化合物（１）と本ピリダジン化合物（２）とを含有する組成物；
本カルボキサミド化合物（１）と本ピリダジン化合物（３）とを含有する組成物；
本カルボキサミド化合物（１）と本ピリダジン化合物（４）とを含有する組成物；
本カルボキサミド化合物（１）と本ピリダジン化合物（５）とを含有する組成物；
本カルボキサミド化合物（１）と本ピリダジン化合物（６）とを含有する組成物； As an aspect of this invention composition, the following are mentioned, for example.
A 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);
本カルボキサミド化合物（２）と本ピリダジン化合物（１）とを含有する組成物；
本カルボキサミド化合物（２）と本ピリダジン化合物（２）とを含有する組成物；
本カルボキサミド化合物（２）と本ピリダジン化合物（３）とを含有する組成物；
本カルボキサミド化合物（２）と本ピリダジン化合物（４）とを含有する組成物；
本カルボキサミド化合物（２）と本ピリダジン化合物（５）とを含有する組成物；
本カルボキサミド化合物（２）と本ピリダジン化合物（６）とを含有する組成物； A composition comprising the present carboxamide compound (2) and the present pyridazine compound (1);
A composition containing the present carboxamide compound (2) and the present pyridazine compound (2);
A composition comprising the present carboxamide compound (2) and the present pyridazine compound (3);
A composition containing the present carboxamide compound (2) and the present pyridazine compound (4);
A composition comprising the present carboxamide compound (2) and the present pyridazine compound (5);
A composition comprising the present carboxamide compound (2) and the present pyridazine compound (6);
本カルボキサミド化合物（３）と本ピリダジン化合物（１）とを含有する組成物；
本カルボキサミド化合物（３）と本ピリダジン化合物（２）とを含有する組成物；
本カルボキサミド化合物（３）と本ピリダジン化合物（３）とを含有する組成物；
本カルボキサミド化合物（３）と本ピリダジン化合物（４）とを含有する組成物；
本カルボキサミド化合物（３）と本ピリダジン化合物（５）とを含有する組成物；
本カルボキサミド化合物（３）と本ピリダジン化合物（６）とを含有する組成物； A composition comprising the present carboxamide compound (3) and the present pyridazine compound (1);
A composition comprising the present carboxamide compound (3) and the present pyridazine compound (2);
A composition comprising the present carboxamide compound (3) and the present pyridazine compound (3);
A composition comprising the present carboxamide compound (3) and the present pyridazine compound (4);
A composition containing the present carboxamide compound (3) and the present pyridazine compound (5);
A composition comprising the present carboxamide compound (3) and the present pyridazine compound (6);
本カルボキサミド化合物（４）と本ピリダジン化合物（１）とを含有する組成物；
本カルボキサミド化合物（４）と本ピリダジン化合物（２）とを含有する組成物；
本カルボキサミド化合物（４）と本ピリダジン化合物（３）とを含有する組成物；
本カルボキサミド化合物（４）と本ピリダジン化合物（４）とを含有する組成物；
本カルボキサミド化合物（４）と本ピリダジン化合物（５）とを含有する組成物；
本カルボキサミド化合物（４）と本ピリダジン化合物（６）とを含有する組成物； A composition comprising the present carboxamide compound (4) and the present pyridazine compound (1);
A composition comprising the present carboxamide compound (4) and the present pyridazine compound (2);
A composition containing the present carboxamide compound (4) and the present pyridazine compound (3);
A composition comprising the present carboxamide compound (4) and the present pyridazine compound (4);
A composition comprising the present carboxamide compound (4) and the present pyridazine compound (5);
A composition comprising the present carboxamide compound (4) and the present pyridazine compound (6);
本カルボキサミド化合物（５）と本ピリダジン化合物（１）とを含有する組成物；
本カルボキサミド化合物（５）と本ピリダジン化合物（２）とを含有する組成物；
本カルボキサミド化合物（５）と本ピリダジン化合物（３）とを含有する組成物；
本カルボキサミド化合物（５）と本ピリダジン化合物（４）とを含有する組成物；
本カルボキサミド化合物（５）と本ピリダジン化合物（５）とを含有する組成物；
本カルボキサミド化合物（５）と本ピリダジン化合物（６）とを含有する組成物； A composition comprising the present carboxamide compound (5) and the present pyridazine compound (1);
A composition comprising the present carboxamide compound (5) and the present pyridazine compound (2);
A composition comprising the present carboxamide compound (5) and the present pyridazine compound (3);
A composition comprising the present carboxamide compound (5) and the present pyridazine compound (4);
A composition comprising the present carboxamide compound (5) and the present pyridazine compound (5);
A composition comprising the present carboxamide compound (5) and the present pyridazine compound (6);
本カルボキサミド化合物（１）と本ピリダジン化合物（１）とを本カルボキサミド化合物（１）／本ピリダジン化合物（１）＝０．１／１～１０／１の重量比で含有する組成物；
本カルボキサミド化合物（１）と本ピリダジン化合物（２）とを本カルボキサミド化合物（１）／本ピリダジン化合物（２）＝０．１／１～１０／１の重量比で含有する組成物；
本カルボキサミド化合物（１）と本ピリダジン化合物（３）とを本カルボキサミド化合物（１）／本ピリダジン化合物（３）＝０．１／１～１０／１の重量比で含有する組成物；
本カルボキサミド化合物（１）と本ピリダジン化合物（４）とを本カルボキサミド化合物（１）／本ピリダジン化合物（４）＝０．１／１～１０／１の重量比で含有する組成物；
本カルボキサミド化合物（１）と本ピリダジン化合物（５）とを本カルボキサミド化合物（１）／本ピリダジン化合物（５）＝０．１／１～１０／１の重量比で含有する組成物；
本カルボキサミド化合物（１）と本ピリダジン化合物（６）とを本カルボキサミド化合物（１）／本ピリダジン化合物（６）＝０．１／１～１０／１の重量比で含有する組成物； 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 (1) and the present pyridazine compound (5) in a weight ratio of the present carboxamide compound (1) / the present pyridazine compound (5) = 0.1 / 1 to 10/1;
A composition comprising the present carboxamide compound (1) and the present pyridazine compound (6) in a weight ratio of the present carboxamide compound (1) / the present pyridazine compound (6) = 0.1 / 1 to 10/1;
本カルボキサミド化合物（２）と本ピリダジン化合物（１）とを本カルボキサミド化合物（２）／本ピリダジン化合物（１）＝０．１／１～１０／１の重量比で含有する組成物；
本カルボキサミド化合物（２）と本ピリダジン化合物（２）とを本カルボキサミド化合物（２）／本ピリダジン化合物（２）＝０．１／１～１０／１の重量比で含有する組成物；
本カルボキサミド化合物（２）と本ピリダジン化合物（３）とを本カルボキサミド化合物（２）／本ピリダジン化合物（３）＝０．１／１～１０／１の重量比で含有する組成物；
本カルボキサミド化合物（２）と本ピリダジン化合物（４）とを本カルボキサミド化合物（２）／本ピリダジン化合物（４）＝０．１／１～１０／１の重量比で含有する組成物；
本カルボキサミド化合物（２）と本ピリダジン化合物（５）とを本カルボキサミド化合物（２）／本ピリダジン化合物（５）＝０．１／１～１０／１の重量比で含有する組成物；
本カルボキサミド化合物（２）と本ピリダジン化合物（６）とを本カルボキサミド化合物（２）／本ピリダジン化合物（６）＝０．１／１～１０／１の重量比で含有する組成物； 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 (2) and the present pyridazine compound (5) in a weight ratio of the present carboxamide compound (2) / the present pyridazine compound (5) = 0.1 / 1 to 10/1;
A composition comprising the present carboxamide compound (2) and the present pyridazine compound (6) in a weight ratio of the present carboxamide compound (2) / the present pyridazine compound (6) = 0.1 / 1 to 10/1;
本カルボキサミド化合物（３）と本ピリダジン化合物（１）とを本カルボキサミド化合物（３）／本ピリダジン化合物（１）＝０．１／１～１０／１の重量比で含有する組成物；
本カルボキサミド化合物（３）と本ピリダジン化合物（２）とを本カルボキサミド化合物（３）／本ピリダジン化合物（２）＝０．１／１～１０／１の重量比で含有する組成物；
本カルボキサミド化合物（３）と本ピリダジン化合物（３）とを本カルボキサミド化合物（３）／本ピリダジン化合物（３）＝０．１／１～１０／１の重量比で含有する組成物；
本カルボキサミド化合物（３）と本ピリダジン化合物（４）とを本カルボキサミド化合物（３）／本ピリダジン化合物（４）＝０．１／１～１０／１の重量比で含有する組成物；
本カルボキサミド化合物（３）と本ピリダジン化合物（５）とを本カルボキサミド化合物（３）／本ピリダジン化合物（５）＝０．１／１～１０／１の重量比で含有する組成物；
本カルボキサミド化合物（３）と本ピリダジン化合物（６）とを本カルボキサミド化合物（３）／本ピリダジン化合物（６）＝０．１／１～１０／１の重量比で含有する組成物； 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 (3) and the present pyridazine compound (5) in a weight ratio of the present carboxamide compound (3) / the present pyridazine compound (5) = 0.1 / 1 to 10/1;
A composition comprising the present carboxamide compound (3) and the present pyridazine compound (6) in a weight ratio of the present carboxamide compound (3) / the present pyridazine compound (6) = 0.1 / 1 to 10/1;
本カルボキサミド化合物（４）と本ピリダジン化合物（１）とを本カルボキサミド化合物（４）／本ピリダジン化合物（１）＝０．１／１～１０／１の重量比で含有する組成物；
本カルボキサミド化合物（４）と本ピリダジン化合物（２）とを本カルボキサミド化合物（４）／本ピリダジン化合物（２）＝０．１／１～１０／１の重量比で含有する組成物；
本カルボキサミド化合物（４）と本ピリダジン化合物（３）とを本カルボキサミド化合物（４）／本ピリダジン化合物（３）＝０．１／１～１０／１の重量比で含有する組成物；
本カルボキサミド化合物（４）と本ピリダジン化合物（４）とを本カルボキサミド化合物（４）／本ピリダジン化合物（４）＝０．１／１～１０／１の重量比で含有する組成物；
本カルボキサミド化合物（４）と本ピリダジン化合物（５）とを本カルボキサミド化合物（４）／本ピリダジン化合物（５）＝０．１／１～１０／１の重量比で含有する組成物；
本カルボキサミド化合物（４）と本ピリダジン化合物（６）とを本カルボキサミド化合物（４）／本ピリダジン化合物（６）＝０．１／１～１０／１の重量比で含有する組成物； 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 (4) and the present pyridazine compound (5) in a weight ratio of the present carboxamide compound (4) / the present pyridazine compound (5) = 0.1 / 1 to 10/1;
A composition comprising the present carboxamide compound (4) and the present pyridazine compound (6) in a weight ratio of the present carboxamide compound (4) / the present pyridazine compound (6) = 0.1 / 1 to 10/1;
本カルボキサミド化合物（５）と本ピリダジン化合物（１）とを本カルボキサミド化合物（５）／本ピリダジン化合物（１）＝０．１／１～１０／１の重量比で含有する組成物；
本カルボキサミド化合物（５）と本ピリダジン化合物（２）とを本カルボキサミド化合物（５）／本ピリダジン化合物（２）＝０．１／１～１０／１の重量比で含有する組成物；
本カルボキサミド化合物（５）と本ピリダジン化合物（３）とを本カルボキサミド化合物（５）／本ピリダジン化合物（３）＝０．１／１～１０／１の重量比で含有する組成物；
本カルボキサミド化合物（５）と本ピリダジン化合物（４）とを本カルボキサミド化合物（５）／本ピリダジン化合物（４）＝０．１／１～１０／１の重量比で含有する組成物；
本カルボキサミド化合物（５）と本ピリダジン化合物（５）とを本カルボキサミド化合物（５）／本ピリダジン化合物（５）＝０．１／１～１０／１の重量比で含有する組成物；
本カルボキサミド化合物（５）と本ピリダジン化合物（６）とを本カルボキサミド化合物（５）／本ピリダジン化合物（６）＝０．１／１～１０／１の重量比で含有する組成物。 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;
A composition comprising the present carboxamide compound (5) and the present pyridazine compound (5) in a weight ratio of the present carboxamide compound (5) / the present pyridazine compound (5) = 0.1 / 1 to 10/1;
A composition comprising the present carboxamide compound (5) and the present pyridazine compound (6) in a weight ratio of the present carboxamide compound (5) / the present pyridazine compound (6) = 0.1 / 1 to 10/1.
　本発明の植物病害防除方法（以下、本発明防除方法と記す。）は、本カルボキサミド化合物と本ピリダジン化合物との有効量を植物又は植物を栽培する土壌に処理することにより行われる。かかる植物としては、例えば、植物の茎葉、植物の種子及び植物の球根が挙げられる。なお、ここで球根とは、鱗茎、球茎、根茎、塊茎、塊根及び担根体を意味する。 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. In addition, a bulb means here a bulb, a bulb, a rhizome, a tuber, a tuberous root, and a root support body.
　本発明防除方法において、本カルボキサミド化合物及び本ピリダジン化合物は、同時期に別々に植物又は植物を栽培する土壌に処理されてもよいが、通常は処理時の簡便性の観点から、本発明組成物として処理される。 In the control method of the present invention, 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
　本発明防除方法において、本カルボキサミド化合物及び本ピリダジン化合物の処理方法としては、例えば、茎葉処理、土壌処理、根部処理及び種子処理が挙げられる。 In the present control method, 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.
　かかる茎葉処理としては、例えば、茎葉散布及び樹幹散布により、栽培されている植物の表面に処理する方法が挙げられる。
　かかる根部処理としては、例えば、本カルボキサミド化合物と本ピリダジン化合物とを含有する薬液に植物の全体又は根部を浸漬する方法、及び、本カルボキサミド化合物と本ピリダジン化合物と固体担体とを含有する固体製剤を植物の根部に付着させる方法が挙げられる。
　かかる土壌処理としては、例えば、土壌散布、土壌混和及び土壌への薬液潅注が挙げられる。
　かかる種子処理としては、例えば、植物病害から保護しようとする植物の種子又は球根への本発明組成物の処理が挙げられ、詳しくは、例えば本発明組成物の懸濁液を霧状にして種子表面若しくは球根表面に吹きつける吹きつけ処理、本発明組成物の水和剤、乳剤若しくはフロアブル剤に少量の水を加えるか、又はそのままで、種子又は球根に塗布する塗沫処理、本発明組成物の溶液に一定時間種子を浸漬する浸漬処理、フィルムコート処理及びペレットコート処理が挙げられる。 Examples of such foliage treatment 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.
Examples of such soil treatment 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. 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 And dipping treatment in which seeds are immersed in the solution for a certain time, film coating treatment and pellet coating treatment.
　本発明防除方法における、本カルボキサミド化合物と本ピリダジン化合物との処理量は、処理する植物の種類、防除対象である植物病害の種類や発生頻度、製剤形態、処理時期、処理方法、処理場所、気象条件等によっても異なる。例えば、植物の茎葉に処理する場合又は植物を栽培する土壌に処理する場合、上記処理量は、本カルボキサミド化合物と本ピリダジン化合物との合計量で、１０００ｍ２あたり、通常１～５００ｇ、好ましくは２～２００ｇ、より好ましくは１０～１００ｇである。また種子への処理における本カルボキサミド化合物と本ピリダジン化合物との処理量は、本カルボキサミド化合物と本ピリダジン化合物との合計量で、種子１ｋｇあたり、通常０．００１～１０ｇ、好ましくは０．０１～１ｇである。
　上記乳剤、水和剤、フロアブル剤等は通常水で希釈して散布することにより処理する。この場合、本カルボキサミド化合物及び本ピリダジン化合物の濃度は、本カルボキサミド化合物及び本ピリダジン化合物の合計での濃度で、通常０．０００５～２重量％、好ましくは０．００５～１重量％である。上記粉剤、粒剤等は通常希釈することなくそのまま処理する。 In the control method of the present invention, 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. For example, in the case of treatment on the foliage of a plant or treatment on soil for cultivating a plant, 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. In this case, 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.
　以下、本発明を製剤例及び試験例にてさらに詳しく説明するが、本発明は以下の例のみに限定されるものではない。なお、以下の例において、部は特にことわりの無い限り重量部を表す。 Hereinafter, the present invention will be described in more detail with formulation examples and test examples, but the present invention is not limited to the following examples. In the following examples, parts represent parts by weight unless otherwise specified.
　まず、本発明組成物に用いる本ピリダジン化合物の参考製造例を説明する。 First, a reference production example of the pyridazine compound used in the composition of the present invention will be described.
参考製造例１
Figure JPOXMLDOC01-appb-I000019
　２－ブロモ－４’－フルオロプロピオフェノン１．８５ｇ、３，５－ジクロロ－２－ピリジル酢酸２．０６ｇおよびアセトニトリル３０ｍＬの混合物に水浴下で、トリエチルアミン１．４１ｇを滴下し、室温で４時間攪拌した後、一晩静置した。該混合物にアセトニトリル３０ｍＬを加え、氷冷下で１，８－ジアザビシクロ[５．４．０]－７－ウンデセン（以下、ＤＢＵと記す）４．５６ｇを滴下した。該混合物を室温で１時間攪拌した。その後、得られた混合物に、室温で攪拌しながら３時間空気を吹き込んだ。反応混合物に氷および１ｍｏｌ／Ｌ塩酸を加え、酢酸エチルで抽出した。有機層を飽和重曹水溶液及び飽和食塩水で順次洗浄し、無水硫酸マグネシウムで乾燥した後、減圧下濃縮して、３－（３，５－ジクロロ－２－ピリジル）－４－（４－フルオロフェニル）－５－ヒドロキシ－５－メチル－２（５Ｈ）－フラノン２．５３ｇを得た。
1Ｈ－ＮＭＲ（ＣＤＣｌ３，ＴＭＳ）δ（ｐｐｍ）：１．７８（３Ｈ，ｓ），５．２９（１Ｈ，ｂｒ　ｓ），６．９７－７．０３（２Ｈ，ｍ），７．４７－７．５１（２Ｈ，ｍ），７．８２（１Ｈ，ｂｒ　ｓ），８．５３（１Ｈ，ｂｒ　ｓ） Reference production example 1
Figure JPOXMLDOC01-appb-I000019
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. Thereafter, air was blown into the obtained mixture for 3 hours while stirring at room temperature. Ice and 1 mol / L hydrochloric acid were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and 3- (3,5-dichloro-2-pyridyl) -4- (4-fluorophenyl). ) -5-hydroxy-5-methyl-2 (5H) -furanone 2.53 g was obtained.
1 H-NMR (CDCl 3 , TMS) δ (ppm): 1.78 (3H, s), 5.29 (1H, br s), 6.97-7.03 (2H, m), 7.47 -7.51 (2H, m), 7.82 (1H, br s), 8.53 (1H, br s)
　３－（３，５－ジクロロ－２－ピリジル）－４－（４－フルオロフェニル）－５－ヒドロキシ－５－メチル－２（５Ｈ）－フラノン２．５３ｇ及び１－ブタノール２５ｍＬの混合物にヒドラジン一水和物０．３６ｇを滴下した後、バス温１１０℃で３時間攪拌した。次いで、反応混合物を０℃まで冷却した。得られた固体を濾過することにより集めた。集められた固体をヘキサン及びｔ－ブチルメチルエーテルの混合溶媒（１：１）を用いて洗浄し、減圧下乾燥して、４－（３，５－ジクロロ－２－ピリジル）－５－（４－フルオロフェニル）－６－メチル－２Ｈ－ピリダジン－３－オン１．３５ｇを得た。
1Ｈ－ＮＭＲ（ＣＤＣｌ３，ＴＭＳ）δ（ｐｐｍ）：２．１３（３Ｈ，ｓ），６．９６－７．００（２Ｈ，ｍ），７．０－７．２（２Ｈ，ｂｒ　ｍ），７．６４（１Ｈ，ｄ，Ｊ＝２．２Ｈｚ），８．３８（１Ｈ，ｄ，Ｊ＝１．９Ｈｚ），１１．７９（１Ｈ，ｂｒ　ｓ） Add hydrazine to a mixture of 2.53 g of 3- (3,5-dichloro-2-pyridyl) -4- (4-fluorophenyl) -5-hydroxy-5-methyl-2 (5H) -furanone and 25 mL of 1-butanol. After 0.36 g of hydrate was added dropwise, the mixture was stirred at a bath temperature of 110 ° C. for 3 hours. The reaction mixture was then cooled to 0 ° C. The resulting solid was collected by filtration. The collected solid was washed with a mixed solvent of hexane and t-butyl methyl ether (1: 1) and dried under reduced pressure to give 4- (3,5-dichloro-2-pyridyl) -5- (4 -Fluorophenyl) -6-methyl-2H-pyridazin-3-one 1.35 g was obtained.
1 H-NMR (CDCl 3 , TMS) δ (ppm): 2.13 (3H, s), 6.96-7.00 (2H, m), 7.0-7.2 (2H, br m) 7.64 (1H, d, J = 2.2 Hz), 8.38 (1H, d, J = 1.9 Hz), 11.79 (1H, br s)
　４－（３，５－ジクロロ－２－ピリジル）－５－（４－フルオロフェニル）－６－メチル－２Ｈ－ピリダジン－３－オン１．１９ｇ及びオキシ塩化リン１５ｇを混合し、３時間加熱還流下に攪拌した。反応混合物を室温まで放冷してから減圧下濃縮した。残渣に酢酸エチルと氷水とを加え、分液した。有機層を飽和重曹水溶液および飽和食塩水で順次洗浄し、無水硫酸ナトリウムで乾燥した後、減圧下濃縮した。得られた残渣１．２８ｇをシリカゲルカラムクロマトグラフィーに付し、本ピリダジン化合物（１）０．８９ｇを得た。
1Ｈ－ＮＭＲ（ＣＤＣｌ３，ＴＭＳ）δ（ｐｐｍ）：２．５７（３Ｈ，ｓ），６．９８－７．０２（２Ｈ，ｍ），７．０９－７．１２（２Ｈ，ｍ），７．６９（１Ｈ，ｄ，Ｊ＝２．２Ｈｚ），８．４３（１Ｈ，ｄ，Ｊ＝２．０Ｈｚ）  4- (3,5-dichloro-2-pyridyl) -5- (4-fluorophenyl) -6-methyl-2H-pyridazin-3-one (1.19 g) and phosphorus oxychloride (15 g) were mixed and heated under reflux for 3 hours. Stir below. The reaction mixture was allowed to cool to room temperature and concentrated under reduced pressure. Ethyl acetate and ice water were added to the residue for liquid separation. The organic layer was washed successively with saturated aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. 1.28 g of the obtained residue was subjected to silica gel column chromatography to obtain 0.89 g of the present pyridazine compound (1).
1 H-NMR (CDCl 3 , TMS) δ (ppm): 2.57 (3H, s), 6.98-7.02 (2H, m), 7.09-7.12 (2H, m), 7.69 (1H, d, J = 2.2 Hz), 8.43 (1H, d, J = 2.0 Hz)
参考製造例２
Figure JPOXMLDOC01-appb-I000020
　４－（３，５－ジクロロ－２－ピリジル）－５－（４－フルオロフェニル）－６－メチル－２Ｈ－ピリダジン－３－オン２．４５ｇ及びオキシ臭化リン８．０ｇを混合し、バス温１００℃で１時間攪拌した。反応混合物を室温まで放冷してから酢酸エチル約２０ｍＬに懸濁させ、氷約１００ｇに注加した。得られた液を重曹水で中和した後、残渣を酢酸エチルで抽出し、分液した。有機層を食塩水で洗浄し、無水硫酸マグネシウムで乾燥した後、減圧下濃縮した。得られた残渣２．９５ｇをシリカゲルカラムクロマトグラフィーに付し、本ピリダジン化合物（２）１．１７ｇを得た。
1Ｈ－ＮＭＲ（ＣＤＣｌ３，ＴＭＳ）δ（ｐｐｍ）：２．５４（３Ｈ，ｓ），６．９８－７．０２（２Ｈ，ｍ），７．１０（２Ｈ，ｂｒ），７．６７（１Ｈ，ｄ，Ｊ＝２．０２Ｈｚ），８．４４（１Ｈ，ｄ，Ｊ＝２．２Ｈｚ）  Reference production example 2
Figure JPOXMLDOC01-appb-I000020
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. 2.95 g of the obtained residue was subjected to silica gel column chromatography to obtain 1.17 g of the present pyridazine compound (2).
1 H-NMR (CDCl 3 , TMS) δ (ppm): 2.54 (3H, s), 6.98-7.02 (2H, m), 7.10 (2H, br), 7.67 ( 1H, d, J = 2.02 Hz), 8.44 (1 H, d, J = 2.2 Hz)
　本ピリダジン化合物（２）０．８５ｇ、シアン化銅０．２２ｇおよびＮ，Ｎ－ジメチルアセトアミド６ｍＬを混合し、３時間加熱還流した。反応混合物を室温まで放冷してから酢酸エチルおよび水各々約５０ｍＬに加え、セライトろ過した。ろ液を分液し、有機層を食塩水で洗浄し、無水硫酸マグネシウムで乾燥した後、減圧下濃縮した。得られた残渣０．４９ｇをシリカゲルカラムクロマトグラフィーに付し、本ピリダジン化合物（３）０．２９ｇを得た。
1Ｈ－ＮＭＲ（ＣＤＣｌ３，ＴＭＳ）δ（ｐｐｍ）：２．７３（３Ｈ，ｓ），６．７０－７．０５（２Ｈ，ｍ），７．１０（２Ｈ，ｂｒ），７．７２（１Ｈ，ｄ，Ｊ＝２．０Ｈｚ），８．４９（１Ｈ，ｄ，Ｊ＝２．０Ｈｚ）  0.85 g of this pyridazine compound (2), 0.22 g of copper cyanide and 6 mL of N, N-dimethylacetamide were mixed and heated to reflux for 3 hours. The reaction mixture was allowed to cool to room temperature, added to about 50 mL each of ethyl acetate and water, and filtered through celite. The filtrate was separated, and the organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. 0.49 g of the obtained residue was subjected to silica gel column chromatography to obtain 0.29 g of the present pyridazine compound (3).
1 H-NMR (CDCl 3 , TMS) δ (ppm): 2.73 (3H, s), 6.70-7.05 (2H, m), 7.10 (2H, br), 7.72 ( 1H, d, J = 2.0 Hz), 8.49 (1H, d, J = 2.0 Hz)
参考製造例３
Figure JPOXMLDOC01-appb-I000021
　本ピリダジン化合物（１）２．２１ｇ、アセチルアセトン鉄（III）０．４２ｇ、テトラヒドロフラン６０ｍＬおよびＮ－メチルピロリドン６ｍＬを混合し、そこへ、氷冷下、攪拌しながら臭化メチルマグネシウム（３．０ｍｏｌ／Ｌジエチルエーテル溶液）６ｍＬを加えた。氷冷下、１時間攪拌した後、反応混合物に１ｍｏｌ／Ｌ塩酸水溶液３０ｍＬを滴下し、水を加えた後、酢酸エチルで抽出した。有機層を重曹水および食塩水で順次洗浄し、無水硫酸マグネシウムで乾燥した後、減圧下濃縮した。得られた残渣２．３５ｇをシリカゲルカラムクロマトグラフィーに付し、本ピリダジン化合物（４）１．１２ｇを得た。
1Ｈ－ＮＭＲ（ＣＤＣｌ３，ＴＭＳ）δ（ｐｐｍ）：２．４３（３Ｈ，ｓ），２．５４（３Ｈ，ｓ），６．９７（２Ｈ，ｂｒ），７．１１（２Ｈ，ｂｒ），７．６５（１Ｈ，ｄ，Ｊ＝２．２Ｈｚ），８．４４（１Ｈ，ｄ，Ｊ＝２．０Ｈｚ）  Reference production example 3
Figure JPOXMLDOC01-appb-I000021
The present pyridazine compound (1) (2.21 g), acetylacetone iron (III) (0.42 g), tetrahydrofuran (60 mL) and N-methylpyrrolidone (6 mL) were mixed, and the mixture was stirred under ice-cooling with methylmagnesium bromide (3.0 mol / mol). 6 mL of L diethyl ether solution) was added. After stirring for 1 hour under ice cooling, 30 mL of a 1 mol / L hydrochloric acid aqueous solution was added dropwise to the reaction mixture, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with aqueous sodium hydrogen carbonate and brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. 2.35 g of the obtained residue was subjected to silica gel column chromatography to obtain 1.12 g of the present pyridazine compound (4).
1 H-NMR (CDCl 3 , TMS) δ (ppm): 2.43 (3H, s), 2.54 (3H, s), 6.97 (2H, br), 7.11 (2H, br) 7.65 (1H, d, J = 2.2 Hz), 8.44 (1H, d, J = 2.0 Hz)
参考製造例４
Figure JPOXMLDOC01-appb-I000022
　本ピリダジン化合物（１）４６．００ｇ及びメタノール２５０ｍＬの混合物にナトリウムメトキシド（２８％メタノール溶液）６２．７０ｇを５分間かけて加え、８時間加熱還流下に攪拌した。反応混合物に氷冷下６ｍｏｌ／Ｌ塩酸水溶液３５ｍＬを加えた後、内容量が約１５０ｇになるまで減圧下に濃縮した。残渣に酢酸エチルと水とを加え、分液した。有機層を飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥した後、内容量が約１２０ｇになるまで減圧下濃縮した。得られた残渣を氷冷下で１時間攪拌した。生じた沈殿を濾過することにより集めた。集められた固体を氷冷した酢酸エチル用いて洗浄し、減圧下乾燥して、本ピリダジン化合物（５）２４．１６ｇを得た。
1Ｈ－ＮＭＲ（ＣＤＣｌ３，ＴＭＳ）δ（ｐｐｍ）：２．４７（３Ｈ，ｓ），４．１１（３Ｈ，ｓ），６．９５－７．００（２Ｈ，ｍ），７．０３－７．１３（２Ｈ，ｂｒ　ｍ），７．６５（１Ｈ，ｄ，Ｊ＝２．０Ｈｚ），８．３８（１Ｈ，ｄ，Ｊ＝２．０Ｈｚ）  Reference production example 4
Figure JPOXMLDOC01-appb-I000022
To a mixture of 46.00 g of this pyridazine compound (1) and 250 mL of methanol, 62.70 g of sodium methoxide (28% methanol solution) was added over 5 minutes, and the mixture was stirred for 8 hours with heating under reflux. After adding 35 mL of a 6 mol / L hydrochloric acid aqueous solution to the reaction mixture under ice cooling, the reaction mixture was concentrated under reduced pressure until the internal volume reached about 150 g. Ethyl acetate and water were added to the residue for liquid separation. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure until the internal volume reached about 120 g. The resulting residue was stirred for 1 hour under ice cooling. The resulting precipitate was collected by filtration. The collected solid was washed with ice-cooled ethyl acetate and dried under reduced pressure to obtain 24.16 g of the present pyridazine compound (5).
1 H-NMR (CDCl 3 , TMS) δ (ppm): 2.47 (3H, s), 4.11 (3H, s), 6.95-7.00 (2H, m), 7.03- 7.13 (2H, br m), 7.65 (1H, d, J = 2.0 Hz), 8.38 (1H, d, J = 2.0 Hz)
参考製造例５
Figure JPOXMLDOC01-appb-I000023
　２－ブロモプロピオフェノン１．７０ｇ、３，５－ジクロロ－２－ピリジル酢酸２．０６ｇおよびアセトニトリル３０ｍＬの混合物に水浴下で、トリエチルアミン１．４１ｇを滴下し、室温で４時間攪拌した後、一晩静置した。該混合物にアセトニトリル３０ｍＬを加え、氷冷下でＤＢＵ４．５６ｇを滴下した。該混合物を室温で１時間攪拌した。その後、得られた混合物に室温で攪拌しながら３時間空気を吹き込んだ。反応混合物に氷および１ｍｏｌ／Ｌ塩酸を加え、酢酸エチルで抽出した。有機層を飽和重曹水溶液及び飽和食塩水で順次洗浄し、無水硫酸マグネシウムで乾燥した後、減圧下濃縮して、３－（３，５－ジクロロ－２－ピリジル）－５－ヒドロキシ－５－メチル－４－フェニル－２（５Ｈ）－フラノン２．３８ｇを得た。
1Ｈ－ＮＭＲ（ＣＤＣｌ3，ＴＭＳ）δ（ｐｐｍ）：１．８１（３Ｈ，ｓ），７．３０－７．５０（５Ｈ，ｍ），７．８２（１Ｈ，ｂｒ　ｓ），８．５３（１Ｈ，ｂｒ　ｓ） Reference production example 5
Figure JPOXMLDOC01-appb-I000023
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. Ice and 1 mol / L hydrochloric acid were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give 3- (3,5-dichloro-2-pyridyl) -5-hydroxy-5-methyl. 2.38 g of -4-phenyl-2 (5H) -furanone was obtained.
1 H-NMR (CDCl 3 , TMS) δ (ppm): 1.81 (3H, s), 7.30-7.50 (5H, m), 7.82 (1H, br s), 8.53 (1H, br s)
　３－（３，５－ジクロロ－２－ピリジル）－５－ヒドロキシ－５－メチル－４－フェニル－２（５Ｈ）－フラノン２．３８ｇ及び１－ブタノール２５ｍＬの混合物にヒドラジン一水和物０．３５ｇを滴下した後、バス温１１０℃で３時間攪拌した。次いで、反応混合物を０℃まで冷却した。得られた固体を濾過することにより集めた。集められた固体をヘキサン及びｔ－ブチルメチルエーテルの混合溶媒（１：１）を用いて洗浄し、減圧下乾燥して、４－（３，５－ジクロロ－２－ピリジル）－６－メチル－５－フェニル－２Ｈ－ピリダジン－３－オン１．２９ｇを得た。
1Ｈ－ＮＭＲ（ＣＤＣｌ３，ＴＭＳ）δ（ｐｐｍ）：２．１４（３Ｈ，ｓ），７．０３－７．４０（５Ｈ，ｍ），７．６２（１Ｈ，ｄ，Ｊ＝２．２Ｈｚ），８．３５（１Ｈ，ｄ，Ｊ＝１．９Ｈｚ），１１．５（１Ｈ，ｂｒ　ｓ） Add hydrazine monohydrate to a mixture of 2.38 g of 3- (3,5-dichloro-2-pyridyl) -5-hydroxy-5-methyl-4-phenyl-2 (5H) -furanone and 25 mL of 1-butanol. After adding 35 g dropwise, the mixture was stirred at a bath temperature of 110 ° C. for 3 hours. The reaction mixture was then cooled to 0 ° C. The resulting solid was collected by filtration. The collected solid was washed with a mixed solvent of hexane and t-butyl methyl ether (1: 1) and dried under reduced pressure to give 4- (3,5-dichloro-2-pyridyl) -6-methyl- 1.29 g of 5-phenyl-2H-pyridazin-3-one was obtained.
1 H-NMR (CDCl 3 , TMS) δ (ppm): 2.14 (3H, s), 7.03-7.40 (5H, m), 7.62 (1H, d, J = 2.2 Hz ), 8.35 (1H, d, J = 1.9 Hz), 11.5 (1H, br s)
　４－（３，５－ジクロロ－２－ピリジル）－６－メチル－５－フェニル－２Ｈ－ピリダジン－３－オン１．１２ｇ及びオキシ塩化リン１５．５ｇを混合し、３時間加熱還流下に攪拌した。反応混合物を室温まで放冷してから減圧下濃縮した。残渣に酢酸エチルと氷水とを加え、分液した。有機層を飽和重曹水溶液および飽和食塩水で順次洗浄し、無水硫酸ナトリウムで乾燥した後、減圧下濃縮した。得られた残渣１．１７ｇをシリカゲルカラムクロマトグラフィーに付し、本ピリダジン化合物（６）０．９９ｇを得た。
1Ｈ－ＮＭＲ（ＣＤＣｌ3，ＴＭＳ）δ（ｐｐｍ）：２．５７（３Ｈ，ｓ），７．１０－７．１２（２Ｈ，ｍ），７．２９－７．３０（３Ｈ，ｍ），７．６６（１Ｈ，ｄ，Ｊ＝２．２Ｈｚ），８．４０（１Ｈ，ｄ，Ｊ＝１．９Ｈｚ）  4- (3,5-dichloro-2-pyridyl) -6-methyl-5-phenyl-2H-pyridazin-3-one (1.12 g) and phosphorus oxychloride (15.5 g) were mixed and stirred for 3 hours while heating under reflux. did. The reaction mixture was allowed to cool to room temperature and concentrated under reduced pressure. Ethyl acetate and ice water were added to the residue for liquid separation. The organic layer was washed successively with saturated aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue 1.17g was attached | subjected to silica gel column chromatography, and 0.99g of this pyridazine compound (6) was obtained.
1 H-NMR (CDCl 3 , TMS) δ (ppm): 2.57 (3H, s), 7.10-7.12 (2H, m), 7.29-7.30 (3H, m), 7.66 (1H, d, J = 2.2 Hz), 8.40 (1 H, d, J = 1.9 Hz)
　次に製剤例を示す。 Next, formulation examples are shown.
製剤例１
　本カルボキサミド化合物（１）を２．５部、本ピリダジン化合物（１）～（６）のいずれかを１．２５部、ポリオキシエチレンスチリルフェニルエーテル１４部、ドデシルベンゼンスルホン酸カルシウム６部およびキシレン７６．２５部をよく混合することにより、各製剤を得る。 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.
製剤例２
　本カルボキサミド化合物（２）を２．５部、本ピリダジン化合物（１）～（６）のいずれかを１．２５部、ポリオキシエチレンスチリルフェニルエーテル１４部、ドデシルベンゼンスルホン酸カルシウム６部およびキシレン７６．２５部をよく混合することにより、各製剤を得る。 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.
製剤例３
　本カルボキサミド化合物（３）を２．５部、本ピリダジン化合物（１）～（６）のいずれかを１．２５部、ポリオキシエチレンスチリルフェニルエーテル１４部、ドデシルベンゼンスルホン酸カルシウム６部およびキシレン７６．２５部をよく混合することにより、各製剤を得る。 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.
製剤例４
　本カルボキサミド化合物（４）を２．５部、本ピリダジン化合物（１）～（６）のいずれかを１．２５部、ポリオキシエチレンスチリルフェニルエーテル１４部、ドデシルベンゼンスルホン酸カルシウム６部およびキシレン７６．２５部をよく混合することにより、各製剤を得る。 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.
製剤例５
　本カルボキサミド化合物（５）を２．５部、本ピリダジン化合物（１）～（６）のいずれかを１．２５部、ポリオキシエチレンスチリルフェニルエーテル１４部、ドデシルベンゼンスルホン酸カルシウム６部およびキシレン７６．２５部をよく混合することにより、各製剤を得る。 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.
製剤例６
　本カルボキサミド化合物（１）を２部、本ピリダジン化合物（１）～（６）のいずれかを８部、ホワイトカーボンとポリオキシエチレンアルキルエーテルサルフェートアンモニウム塩との混合物（重量割合１：１）３５部および水５５部を混合し、湿式粉砕法で微粉砕することにより、各製剤を得る。 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.
製剤例７
　本カルボキサミド化合物（２）を２部、本ピリダジン化合物（１）～（６）のいずれかを８部、ホワイトカーボンとポリオキシエチレンアルキルエーテルサルフェートアンモニウム塩との混合物（重量割合１：１）３５部および水５５部を混合し、湿式粉砕法で微粉砕することにより、各製剤を得る。 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.
製剤例８
　本カルボキサミド化合物（３）を２部、本ピリダジン化合物（１）～（６）のいずれかを８部、ホワイトカーボンとポリオキシエチレンアルキルエーテルサルフェートアンモニウム塩との混合物（重量割合１：１）３５部および水５５部を混合し、湿式粉砕法で微粉砕することにより、各製剤を得る。 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.
製剤例９
　本カルボキサミド化合物（４）を２部、本ピリダジン化合物（１）～（６）のいずれかを８部、ホワイトカーボンとポリオキシエチレンアルキルエーテルサルフェートアンモニウム塩との混合物（重量割合１：１）３５部および水５５部を混合し、湿式粉砕法で微粉砕することにより、各製剤を得る。 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.
製剤例１０
　本カルボキサミド化合物（５）を２部、本ピリダジン化合物（１）～（６）のいずれかを８部、ホワイトカーボンとポリオキシエチレンアルキルエーテルサルフェートアンモニウム塩との混合物（重量割合１：１）３５部および水５５部を混合し、湿式粉砕法で微粉砕することにより、各製剤を得る。 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.
製剤例１１
　本カルボキサミド化合物（１）を５部、本ピリダジン化合物（１）～（６）のいずれかを１０部、ソルビタントリオレエート１．５部およびポリビニルアルコール２部を含む水溶液２８．５部を混合し、湿式粉砕法で微粉砕する。得られた粉砕物にキサンタンガム０．０５部およびアルミニウムマグネシウムシリケート０．１部を含む水溶液４５部を加え、さらにプロピレングリコール１０部を加えて攪拌混合し、各製剤を得る。 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.
製剤例１２
　本カルボキサミド化合物（２）を５部、本ピリダジン化合物（１）～（６）のいずれかを１０部、ソルビタントリオレエート１．５部およびポリビニルアルコール２部を含む水溶液２８．５部を混合し、湿式粉砕法で微粉砕する。得られた粉砕物にキサンタンガム０．０５部およびアルミニウムマグネシウムシリケート０．１部を含む水溶液４５部を加え、さらにプロピレングリコール１０部を加えて攪拌混合し、各製剤を得る。 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.
製剤例１３
　本カルボキサミド化合物（３）を５部、本ピリダジン化合物（１）～（６）のいずれかを１０部、ソルビタントリオレエート１．５部およびポリビニルアルコール２部を含む水溶液２８．５部を混合し、湿式粉砕法で微粉砕する。得られた粉砕物にキサンタンガム０．０５部およびアルミニウムマグネシウムシリケート０．１部を含む水溶液４５部を加え、さらにプロピレングリコール１０部を加えて攪拌混合し、各製剤を得る。 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.
製剤例１４
　本カルボキサミド化合物（４）を５部、本ピリダジン化合物（１）～（６）のいずれかを１０部、ソルビタントリオレエート１．５部およびポリビニルアルコール２部を含む水溶液２８．５部を混合し、湿式粉砕法で微粉砕する。得られた粉砕物にキサンタンガム０．０５部およびアルミニウムマグネシウムシリケート０．１部を含む水溶液４５部を加え、さらにプロピレングリコール１０部を加えて攪拌混合し、各製剤を得る。 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.
製剤例１５
　本カルボキサミド化合物（５）を５部、本ピリダジン化合物（１）～（６）のいずれかを１０部、ソルビタントリオレエート１．５部およびポリビニルアルコール２部を含む水溶液２８．５部を混合し、湿式粉砕法で微粉砕する。得られた粉砕物にキサンタンガム０．０５部およびアルミニウムマグネシウムシリケート０．１部を含む水溶液４５部を加え、さらにプロピレングリコール１０部を加えて攪拌混合し、各製剤を得る。 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.
製剤例１６
　本カルボキサミド化合物（１）を１部、本ピリダジン化合物（１）～（６）のいずれかを４部、合成含水酸化珪素１部、リグニンスルホン酸カルシウム２部、ベントナイト３０部およびカオリンクレー６２部をよく粉砕混合し、水を加えてよく練り合せた後、造粒乾燥することにより、各製剤を得る。 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.
製剤例１７
　本カルボキサミド化合物（２）を１部、本ピリダジン化合物（１）～（６）のいずれかを４部、合成含水酸化珪素１部、リグニンスルホン酸カルシウム２部、ベントナイト３０部およびカオリンクレー６２部をよく粉砕混合し、水を加えてよく練り合せた後、造粒乾燥することにより、各製剤を得る。 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.
製剤例１８
　本カルボキサミド化合物（３）を１部、本ピリダジン化合物（１）～（６）のいずれかを４部、合成含水酸化珪素１部、リグニンスルホン酸カルシウム２部、ベントナイト３０部およびカオリンクレー６２部をよく粉砕混合し、水を加えてよく練り合せた後、造粒乾燥することにより、各製剤を得る。 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.
製剤例１９
　本カルボキサミド化合物（４）を１部、本ピリダジン化合物（１）～（６）のいずれかを４部、合成含水酸化珪素１部、リグニンスルホン酸カルシウム２部、ベントナイト３０部およびカオリンクレー６２部をよく粉砕混合し、水を加えてよく練り合せた後、造粒乾燥することにより、各製剤を得る。 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.
製剤例２０
　本カルボキサミド化合物（５）を１部、本ピリダジン化合物（１）～（６）のいずれかを４部、合成含水酸化珪素１部、リグニンスルホン酸カルシウム２部、ベントナイト３０部およびカオリンクレー６２部をよく粉砕混合し、水を加えてよく練り合せた後、造粒乾燥することにより、各製剤を得る。 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.
製剤例２１
　本カルボキサミド化合物（１）を１２．５部、本ピリダジン化合物（１）～（６）のいずれかを３７．５部、リグニンスルホン酸カルシウム３部、ラウリル硫酸ナトリウム２部および合成含水酸化珪素４５部をよく粉砕混合することにより、各製剤を得る。 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.
製剤例２２
　本カルボキサミド化合物（２）を１２．５部、本ピリダジン化合物（１）～（６）のいずれかを３７．５部、リグニンスルホン酸カルシウム３部、ラウリル硫酸ナトリウム２部および合成含水酸化珪素４５部をよく粉砕混合することにより、各製剤を得る。 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.
製剤例２３
　本カルボキサミド化合物（３）を１２．５部、本ピリダジン化合物（１）～（６）のいずれかを３７．５部、リグニンスルホン酸カルシウム３部、ラウリル硫酸ナトリウム２部および合成含水酸化珪素４５部をよく粉砕混合することにより、各製剤を得る。 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.
製剤例２４
　本カルボキサミド化合物（４）を１２．５部、本ピリダジン化合物（１）～（６）のいずれかを３７．５部、リグニンスルホン酸カルシウム３部、ラウリル硫酸ナトリウム２部および合成含水酸化珪素４５部をよく粉砕混合することにより、各製剤を得る。 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.
製剤例２５
　本カルボキサミド化合物（５）を１２．５部、本ピリダジン化合物（１）～（６）のいずれかを３７．５部、リグニンスルホン酸カルシウム３部、ラウリル硫酸ナトリウム２部および合成含水酸化珪素４５部をよく粉砕混合することにより、各製剤を得る。 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.
製剤例２６
　本カルボキサミド化合物（１）を３部、本ピリダジン化合物（１）～（６）のいずれかを２部、カオリンクレー８５部およびタルク１０部をよく粉砕混合することにより、各製剤を得る。 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.
製剤例２７
　本カルボキサミド化合物（２）を３部、本ピリダジン化合物（１）～（６）のいずれかを２部、カオリンクレー８５部およびタルク１０部をよく粉砕混合することにより、各製剤を得る。 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.
製剤例２８
　本カルボキサミド化合物（３）を３部、本ピリダジン化合物（１）～（６）のいずれかを２部、カオリンクレー８５部およびタルク１０部をよく粉砕混合することにより、各製剤を得る。 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.
製剤例２９
　本カルボキサミド化合物（４）を３部、本ピリダジン化合物（１）～（６）のいずれかを２部、カオリンクレー８５部およびタルク１０部をよく粉砕混合することにより、各製剤を得る。 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.
製剤例３０
　本カルボキサミド化合物（５）を３部、本ピリダジン化合物（１）～（６）のいずれかを２部、カオリンクレー８５部およびタルク１０部をよく粉砕混合することにより、各製剤を得る。 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.
　次に試験例を示す。 Next, test examples are shown.
試験例１
　プラスチックポットに土壌を詰め、この土壌にコムギ（品種；アポジー）を播種し、温室内で１４日間生育させた。供試化合物をＣＥＣカクテル（シクロヘキサノン：ソルポール（登録商標）２６８０Ｘ（東邦化学工業製）＝５：１（体積比））に溶解し製剤とした後、該製剤を水で希釈し所定濃度にし、該希釈液を上記コムギの葉面に充分に付着するように茎葉散布した。散布後植物を風乾し、２日後にコムギ葉枯病菌（Ｍｙｃｏｓｐｈａｅｒｅｌｌａ　ｇｒａｍｉｎｉｃｏｌａ）の分生胞子の水懸濁液（約１，０００，０００個／ｍｌ）を噴霧接種した。接種後はじめは１８℃多湿下に３日間置き、多湿下から出して１８℃恒温室に１４日間置くことによりコムギを栽培した（これを処理区とする。）。その後、コムギ葉枯病の病斑面積を調査した。
　一方、供試化合物の希釈液を茎葉散布しないこと以外は処理区と同様にコムギを栽培した（これを無処理区とする。）。処理区と同様にコムギ葉枯病の病斑面積を調査した。
　処理区及び無処理区それぞれの病斑面積から、下記式（１）により処理区の効力を求めた。その結果を［表１］乃至［表６］に示す。
Figure JPOXMLDOC01-appb-I000024
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. The test compound was dissolved in a CEC cocktail (cyclohexanone: Solpol (registered trademark) 2680X (manufactured by Toho Chemical Co., Ltd.) = 5: 1 (volume ratio)) to prepare a preparation, and the preparation was diluted with water to a predetermined concentration, The diluted solution was sprayed on the foliage so that the diluted solution was sufficiently attached to the leaf surface of the wheat. After spraying, the plants were air-dried, and two days later, an aqueous suspension (about 1,000,000 / ml) of conidia of wheat leaf blight fungus (Mycosphaerella gramicola) was spray-inoculated. After inoculation, the wheat was first cultivated by placing it in a humid room at 18 ° C. for 3 days, and then leaving it in a humid room at 18 ° C. for 14 days (this is referred to as a treatment zone). Thereafter, the lesion area of wheat leaf blight was investigated.
On the other hand, wheat was cultivated in the same manner as in the treated area except that the diluted solution of the test compound was not sprayed on the foliage (this was designated as an untreated area). Similar to the treatment area, the lesion area of wheat leaf blight was investigated.
The efficacy of the treated area was determined by the following formula (1) from the lesion areas of the treated area and the untreated area. The results are shown in [Table 1] to [Table 6].
Figure JPOXMLDOC01-appb-I000024
Figure JPOXMLDOC01-appb-T000025
Figure JPOXMLDOC01-appb-T000025
Figure JPOXMLDOC01-appb-T000026
Figure JPOXMLDOC01-appb-T000026
Figure JPOXMLDOC01-appb-T000027
Figure JPOXMLDOC01-appb-T000027
Figure JPOXMLDOC01-appb-T000028
Figure JPOXMLDOC01-appb-T000028
Figure JPOXMLDOC01-appb-T000029
Figure JPOXMLDOC01-appb-T000029
Figure JPOXMLDOC01-appb-T000030
Figure JPOXMLDOC01-appb-T000030

Claims (5)

  1. 　式（Ｉ）
    Figure JPOXMLDOC01-appb-I000001
    〔式中、
    Ｒ１は水素原子又はメチル基を表し、
    Ｒ２はメチル基、ジフルオロメチル基又はトリフルオロメチル基を表す。〕
    で示されるカルボキサミド化合物と、
    式（ＩＩ）
    Figure JPOXMLDOC01-appb-I000002
    〔式中、
    Ａ1は塩素原子、臭素原子、シアノ基、メチル基又はメトキシ基を表し、
    Ａ2はフッ素原子又は水素原子を表し、
    Ａ3はハロゲン原子を表し、
    Ａ4はハロゲン原子、メトキシ基又は水素原子を表す。〕
    で示されるピリダジン化合物とを含有する植物病害防除組成物。     Formula (I)
    Figure JPOXMLDOC01-appb-I000001
    [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)
    Figure JPOXMLDOC01-appb-I000002
    [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 composition containing the pyridazine compound shown by these.
  2. 　カルボキサミド化合物とピリダジン化合物との重量比が、カルボキサミド化合物／ピリダジン化合物＝０．１／１～１０／１である請求項１記載の植物病害防除組成物。 2. The plant disease control composition according to claim 1, wherein the weight ratio of the carboxamide compound to the pyridazine compound is carboxamide compound / pyridazine compound = 0.1 / 1 to 10/1.
  3. 　式（Ｉ）
    Figure JPOXMLDOC01-appb-I000003
    〔式中、
    Ｒ１は水素原子又はメチル基を表し、
    Ｒ２はメチル基、ジフルオロメチル基又はトリフルオロメチル基を表す。〕
    で示されるカルボキサミド化合物と、
    式（ＩＩ）
    Figure JPOXMLDOC01-appb-I000004
    〔式中、
    Ａ1は塩素原子、臭素原子、シアノ基、メチル基又はメトキシ基を表し、
    Ａ2はフッ素原子又は水素原子を表し、
    Ａ3はハロゲン原子を表し、
    Ａ4はハロゲン原子、メトキシ基又は水素原子を表す。〕
    で示されるピリダジン化合物との有効量を、植物又は植物を栽培する土壌に処理する工程を含む植物病害防除方法。     Formula (I)
    Figure JPOXMLDOC01-appb-I000003
    [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)
    Figure JPOXMLDOC01-appb-I000004
    [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.
  4. 　カルボキサミド化合物とピリダジン化合物との重量比が、カルボキサミド化合物／ピリダジン化合物＝０．１／１～１０／１である請求項３記載の植物病害防除方法。 The plant disease control method according to claim 3, wherein the weight ratio of the carboxamide compound to the pyridazine compound is carboxamide compound / pyridazine compound = 0.1 / 1 to 10/1.
  5. 　植物又は植物を栽培する土壌が、コムギ又はコムギを栽培する土壌である請求項３又は４記載の植物病害防除方法。 The plant disease control method according to claim 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.
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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1986002641A1 (en) * 1984-10-29 1986-05-09 Sumitomo Chemical Company, Limited Pyrazolecarboxamide derivatives, process for their preparation, and bactericides containing them as effective ingredients
JPH06505252A (en) * 1991-01-28 1994-06-16 モンサント・カンパニー 3-difluoromethylpyrazole carboxamide fungicide
WO2007066601A1 (en) * 2005-12-07 2007-06-14 Sumitomo Chemical Company, Limited Pyridazine compound and use thereof

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1986002641A1 (en) * 1984-10-29 1986-05-09 Sumitomo Chemical Company, Limited Pyrazolecarboxamide derivatives, process for their preparation, and bactericides containing them as effective ingredients
JPH06505252A (en) * 1991-01-28 1994-06-16 モンサント・カンパニー 3-difluoromethylpyrazole carboxamide fungicide
WO2007066601A1 (en) * 2005-12-07 2007-06-14 Sumitomo Chemical Company, Limited Pyridazine compound and use thereof

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