JP2012036143A - Plant disease control composition and application for same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a composition exhibiting excellent controlling effects on plant diseases.SOLUTION: The plant disease control composition containing a pyridazine compound expressed by formula (I) (wherein, Rindicates a chlorine atom, a bromine atom, a cyano group, a methyl group, or a methoxy group, Rindicates a fluorine atom or a hydrogen atom; and R, Reach indicate a halogen atom or the like) and one or more kinds of carboxamide compound selected from the group (A) exhibits the excellent controlling effects on the plant diseases. The group (A) includes bixafen, isopyrazam, boscalid, fluopyram, fluxapyroxad, sedaxane, penflufen, flutolanil, mepronil, carboxin, thifluzamide, penthiopyrad and furametpyr.

Description

  The present invention relates to a plant disease control composition and use thereof.

  Conventionally, many compounds have been developed and put into practical use for controlling plant diseases (see, for example, Patent Document 1).

International Publication No. 2007/066661 Pamphlet

  An object of the present invention is to provide a composition having an excellent control effect against plant diseases.

〔式中、
Ｒ¹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、
Ｒ²はフッ素原子又は水素原子を表し、
Ｒ³はハロゲン原子を表し、
Ｒ⁴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、
群（Ａ）より選ばれる１種以上のカルボキサミド化合物とを含有する植物病害防除組成物。
群（Ａ）：
ビキサフェン（bixafen）、イソピラザム（isopyrazam）、ボスカリド（boscalid）、フルオピラム（fluopyram）、フルキサピロキサド（fluxapyroxad）、セダキサン（sedaxane）、ペンフルフェン（penflufen）、フルトラニル（flutolanil）、メプロニル（mepronil）、カルボキシン（carboxin）、チフルザミド（thifluxamide）、ペンチオピラド（penthiopyrad）及びフラメトピル（furametpyr）からなる群。
［２］ ピリダジン化合物とカルボキサミド化合物との重量比が、ピリダジン化合物／カルボキサミド化合物＝０．１／１〜１０／１である［１］記載の植物病害防除組成物。
［３］ 式（Ｉ）

〔式中、
Ｒ¹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、
Ｒ²はフッ素原子又は水素原子を表し、
Ｒ³はハロゲン原子を表し、
Ｒ⁴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、
群（Ａ）より選ばれる１種以上のカルボキサミド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。
群（Ａ）：
ビキサフェン、イソピラザム、ボスカリド、フルオピラム、フルキサピロキサド、セダキサン、ペンフルフェン、フルトラニル、メプロニル、カルボキシン、チフルザミド、ペンチオピラド及びフラメトピルからなる群。
［４］ ピリダジン化合物とカルボキサミド化合物との重量比が、ピリダジン化合物／カルボキサミド化合物＝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。 As a result of studies to find a composition having an excellent control effect against plant diseases, the present inventor has found that a pyridazine compound represented by the following formula (I) and one or more carboxamides selected from the following group (A): It has been found that a plant disease control composition containing a compound has an excellent control effect against plant diseases, and has led to the present invention.
That is, the present invention is as follows.
[1] Formula (I)

[Where,
R ¹ represents a chlorine atom, a bromine atom, a cyano group, a methyl group or a methoxy group,
R ² represents a fluorine atom or a hydrogen atom,
R ³ represents a halogen atom,
R ⁴ represents a halogen atom, a methoxy group or a hydrogen atom. ]
A pyridazine compound represented by
A plant disease control composition comprising one or more carboxamide compounds selected from the group (A).
Group (A):
Bixafen, isopyrazam, boscalid, fluopyram, fluxapyroxad, sedaxane, penflufen, flutolanil, mepronil, mepronil, mepronil (Carboxin), thifluxamide, penthiopyrad, and furametpyr.
[2] The plant disease control composition according to [1], wherein the weight ratio of the pyridazine compound and the carboxamide compound is pyridazine compound / carboxamide compound = 0.1 / 1 to 10/1.
[3] Formula (I)

[Where,
R ¹ represents a chlorine atom, a bromine atom, a cyano group, a methyl group or a methoxy group,
R ² represents a fluorine atom or a hydrogen atom,
R ³ represents a halogen atom,
R ⁴ represents a halogen atom, a methoxy group or a hydrogen atom. ]
A pyridazine compound represented by
A method for controlling plant diseases, comprising a step of treating an effective amount with one or more carboxamide compounds selected from the group (A) on a plant or soil for growing plants.
Group (A):
A group consisting of bixafen, isopyrazam, boscalid, fluopyram, floxapyroxad, sedaxane, penflufen, flutolanil, mepronyl, carboxin, tifluzamide, pentiopyrad, and furametopir.
[4] The method for controlling plant diseases according to [3], wherein the weight ratio of the pyridazine compound to the carboxamide compound is pyridazine compound / carboxamide compound = 0.1 / 1 to 10/1.
[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.

  According to the present invention, plant diseases can be controlled.

〔式中、
Ｒ¹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、
Ｒ²はフッ素原子又は水素原子を表し、
Ｒ³はハロゲン原子を表し、
Ｒ⁴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、群（Ａ）より選ばれる１種以上の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。）とを含有する。
群（Ａ）：
ビキサフェン、イソピラザム、ボスカリド、フルオピラム、フルキサピロキサド、セダキサン、ペンフルフェン、フルトラニル、メプロニル、カルボキシン、チフルザミド、ペンチオピラド及びフラメトピルからなる群。 The plant disease control composition of the present invention (hereinafter referred to as the present composition) has the formula (I)

[Where,
R ¹ represents a chlorine atom, a bromine atom, a cyano group, a methyl group or a methoxy group,
R ² represents a fluorine atom or a hydrogen atom,
R ³ represents a halogen atom,
R ⁴ represents a halogen atom, a methoxy group or a hydrogen atom. ]
And one or more carboxamide compounds selected from the group (A) (hereinafter referred to as the present carboxamide compound).
Group (A):
A group consisting of bixafen, isopyrazam, boscalid, fluopyram, floxapyroxad, sedaxane, penflufen, flutolanil, mepronyl, carboxin, tifluzamide, pentiopyrad, and furametopir.

The pyridazine compound used in the composition of the present invention will be described.
In the formula (I), examples of the halogen atom represented by each of R ³ and R ⁴ include a chlorine atom, a bromine atom, and a fluorine atom.

  As an aspect of this pyridazine compound, the following pyridazine compounds are mention | raise | lifted, for example.

A pyridazine compound represented by formula (I), wherein R ¹ is a chlorine atom or a methoxy group;
A pyridazine compound represented by formula (I), wherein R ¹ is a chlorine atom;
A pyridazine compound represented by formula (I), wherein R ¹ is a methyl group;
A pyridazine compound represented by formula (I), wherein R ² is a fluorine atom;
A pyridazine compound represented by formula (I), wherein R ² is a hydrogen atom;
A pyridazine compound represented by formula (I), wherein R ³ is a chlorine atom or a fluorine atom;
A pyridazine compound represented by formula (I), wherein R ³ is a chlorine atom;
A pyridazine compound represented by formula (I), wherein R ⁴ is a chlorine atom, a fluorine atom or a hydrogen atom;
A pyridazine compound represented by formula (I), wherein R ⁴ is a chlorine atom;
A pyridazine compound represented by formula (I), wherein R ³ is a chlorine atom or a fluorine atom, and R ⁴ is a chlorine atom;
A pyridazine compound represented by formula (I), wherein R ³ is a chlorine atom and R ⁴ is a chlorine atom;
A pyridazine compound represented by formula (I), wherein R ¹ is a chlorine atom or a methoxy group, R ³ is a chlorine atom or a fluorine atom, and R ⁴ is a chlorine atom;
A pyridazine compound represented by formula (I), wherein R ¹ is a chlorine atom, R ³ is a chlorine atom or a fluorine atom, and R ⁴ is a chlorine atom;
A pyridazine compound represented by formula (I), wherein R ¹ is a chlorine atom or a methoxy group, R ³ is a chlorine atom, and R ⁴ is a chlorine atom;
A pyridazine compound represented by formula (I), wherein R ¹ is a chlorine atom, R ³ is a chlorine atom, and R ⁴ is a chlorine atom.

Next, specific examples of the pyridazine compound will be shown.
In formula (I), R ¹ is a chlorine atom, R ² is a fluorine atom, R ³ is a chlorine atom, and R ⁴ is a chlorine atom (hereinafter referred to as the present pyridazine compound (1)). .);
In formula (I), R ¹ is a bromine atom, R ² is a fluorine atom, R ³ is a chlorine atom, and R ⁴ is a chlorine atom (hereinafter referred to as the present pyridazine compound (2)). .);
In the formula (I), R ¹ is a cyano group, R ² is a fluorine atom, R ³ is a chlorine atom, and R ⁴ is a chlorine atom (hereinafter referred to as the present pyridazine compound (3)). .);
In formula (I), R ¹ is a methyl group, R ² is a fluorine atom, R ³ is a chlorine atom, and R ⁴ is a chlorine atom (hereinafter referred to as the present pyridazine compound (4)). .);
In formula (I), R ¹ is a methoxy group, R ² is a fluorine atom, R ³ is a chlorine atom, and R ⁴ is a chlorine atom (hereinafter referred to as the present pyridazine compound (5)). .);
In formula (I), R ¹ is a chlorine atom, R ² is a hydrogen atom, R ³ is a chlorine atom, and R ⁴ is a chlorine atom (hereinafter referred to as the present pyridazine compound (6)). .)

Next, the manufacturing method of this pyridazine compound is demonstrated.
Among the pyridazine compounds, a pyridazine compound in which R ¹ is a chlorine atom, a bromine atom, a methyl group or a methoxy group in the formula (I) is produced, for example, by the method described in International Publication No. 2007/066661 pamphlet. be able to.

〔式中、Ｒ²、Ｒ³、Ｒ⁴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（Ｉ−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（Ｉ−２）を単離することができる。化合物（Ｉ−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 (I-2) in which R ¹ is a cyano group in formula (I) is, for example, the compound in which R ¹ is a bromine atom in formula (I) among the pyridazine compounds ( It can be produced by reacting I-1) with copper cyanide.

[Wherein R ² , R ³ and R ⁴ represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used for the reaction include aprotic polar solvents such as N, N-dimethylacetamide.
The amount of copper cyanide used in the reaction is usually 1 to 1.5 mol per 1 mol of compound (I-1).
The reaction temperature of the reaction 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 (I-2) can be isolated. Compound (I-2) can be further purified by chromatography, recrystallization and the like.

〔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。

〔式中、Ｒ²、Ｒ³、Ｒ⁴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（Ｉ−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（Ｉ−４）を単離することができる。単離された化合物（Ｉ−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 (I-4) in which R ¹ is a methyl group in the formula (I) is the compound (I-) in which R ¹ is a chlorine atom in the formula (I) among the pyridazine compounds. 3) is converted to formula (II)

[Wherein, X represents a bromine atom or a chlorine atom. ]
It can manufacture by making it react with the Grignard reagent shown by presence of an iron catalyst.

[Wherein R ² , R ³ and R ⁴ represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include tetrahydrofuran, diethyl ether and N-methylpyrrolidone, and a mixed solvent 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 0.01 to 0.3 mol with respect to 1 mol of compound (I-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 obtained organic layer is washed with water, dried, concentrated, and the like, so that the compound (I-4) is obtained. Can be separated. The isolated compound (I-4) can be further purified by chromatography, recrystallization and the like.

  All of the present carboxamide compounds are known compounds. For example, “THE PESTICIDE MANUAL-14th EDITION (BCPC) ISBN 190139142”, International Publication No. 2003/077055, International Publication No. 2004/035589, International Publication No. 2004/016088 pamphlet, WO 2006/088343 pamphlet, WO 2006/015866 pamphlet and WO 2003/010149 pamphlet. These compounds can be obtained from commercial preparations or synthesized by known methods.

  The weight ratio of the present pyridazine compound to the present carboxamide compound in the composition of the present invention is usually the present pyridazine compound / the present carboxamide compound = 0.01 / 1 to 500/1, preferably 0.1 / 1 to 10/1. It is.

The composition of the present invention may be a mixture of the pyridazine compound and the carboxamide compound itself, but the composition of the present invention is usually mixed with the pyridazine compound, the carboxamide compound and an inert carrier, and if necessary, a surface active agent. It is formulated into oils, emulsions, flowables, wettable powders, granular wettable powders, powders, granules and the like by adding additives and other formulation adjuvants. Such a preparation can be used as a plant disease control agent as it is or with addition of other inactive ingredients.
The present composition contains the present pyridazine compound and the present carboxamide compound in a total amount of usually 0.1 to 99% by weight, preferably 0.2 to 90% by weight, more preferably 1 to 80% by weight.

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. Nonionic surfactants such as activators and polyoxyethylene alkyl aryl ethers, polyoxyethylene alkyl polyoxypropylene block copolymers, sorbitan fatty acid esters, and cationic surfactants such as alkyltrimethylammonium salts.
Examples of other adjuvants for preparation include water-soluble polymers such as polyvinyl alcohol and polyvinyl pyrrolidone, gum arabic, alginic acid and salts thereof, 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.

  The composition of the present invention is also prepared by formulating the pyridazine compound and the carboxamide compound by the above-described methods, and then diluting with water as necessary to mix the respective formulations or their dilutions. You can also

  The 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: 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 (Ustylago tritici), Tuna scab (Tilleletia carripe), Pseucercosporella morposis (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 polysoria), gray leaf spot disease Rhizoctonia solani due to seedling.

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) , Phytophactora catorum.
Pear Diseases: Black Star Disease (Venturia nashicola, V. pirina), Black Spot Disease (Alternaria alternata Japan pearpathotype), 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 gingulata), powdery mildew (Uncinula adipelodia), black rot (Gikonivaladi) .
Oyster diseases: Anthracnose (Gloeosporium kaki), deciduous leaf disease (Cercospora kaki, Mycosphaerella nawae).
Diseases of cucurbits: Anthracnose (Colletotrichum lagenarium), powdery mildew (Sphaerotheca furiginea), vine blight (Mycosphaerella meloniis), vine scab (Fusarium oxysporum), por disease (fusarium oxysporum) ), 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)

Diseases of soybean: Purcosis (Cercospora kikuchii), black scab (Elsinoe glycines), black spot (Diaporthe phasolorum 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 (Pestalotiosis 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 irregulare, Pythium ultimatum)
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.

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.

  The above-mentioned plant may be a plant to which resistance is imparted by a gene recombination technique.

Of these, a high control effect is expected especially against plant diseases occurring in wheat.
Among the plant diseases occurring in these crops, wheat diseases that are expected to have particularly high efficacy include powdery mildew (Erysiphe graminis), red mold disease (Fusarium gramaminerum, F. avenacerum, F. culmorum, Microdochium). nivale, rust disease (Puccinia striformis, P. graminis, P. recondita), red snow rot (Micronetriella nivale), snow rot microspora nuclear disease (Typhula sp.), naked scab (Ustira scab) (Tilletia caries), eye spot disease (Pseudocercosporella herpotriochoides), leaf blight (Myco) sphaerella gramicola), blight (Stagonospora nodorum), macular disease (Pyrenophora tritici-replentis);
Etc.

As an aspect of this invention composition, the following are mentioned, for example.
A composition containing the present pyridazine compound (1) and bixaphene;
A composition containing the present pyridazine compound (1) and isopyrazam;
A composition containing the pyridazine compound (1) and boscalid;
A composition containing the pyridazine compound (1) and fluopyram;
A composition containing the present pyridazine compound (1) and floxapyroxad;
A composition containing the pyridazine compound (1) and sedaxane;
A composition containing the pyridazine compound (1) and penflufen;
A composition containing the pyridazine compound (1) and flutolanil;
A composition containing the pyridazine compound (1) and mepronil;
A composition containing the pyridazine compound (1) and carboxin;
A composition containing the present pyridazine compound (1) and tifluzamide;
A composition comprising the present pyridazine compound (1) and penthiopyrad;
A composition containing the pyridazine compound (1) and furametopil;

A composition containing the present pyridazine compound (2) and bixaphene;
A composition containing the present pyridazine compound (2) and isopyrazam;
A composition containing the present pyridazine compound (2) and boscalid;
A composition containing the present pyridazine compound (2) and fluopyram;
A composition comprising the present pyridazine compound (2) and floxapyroxad;
A composition containing the pyridazine compound (2) and sedaxane;
A composition containing the present pyridazine compound (2) and penflufen;
A composition containing the present pyridazine compound (2) and flutolanil;
A composition containing the present pyridazine compound (2) and mepronil;
A composition containing the present pyridazine compound (2) and carboxin;
A composition containing the present pyridazine compound (2) and tifluzamide;
A composition containing the present pyridazine compound (2) and penthiopyrad;
A composition containing the present pyridazine compound (2) and furametopir;

A composition containing the present pyridazine compound (3) and bixaphene;
A composition containing the present pyridazine compound (3) and isopyrazam;
A composition containing the pyridazine compound (3) and boscalid;
A composition containing the present pyridazine compound (3) and fluopyram;
A composition containing the present pyridazine compound (3) and floxapyroxad;
A composition containing the pyridazine compound (3) and sedaxane;
A composition containing the pyridazine compound (3) and penflufen;
A composition containing the pyridazine compound (3) and flutolanil;
A composition containing the pyridazine compound (3) and mepronil;
A composition containing the present pyridazine compound (3) and carboxin;
A composition containing the present pyridazine compound (3) and tifluzamide;
A composition containing the present pyridazine compound (3) and penthiopyrad;
A composition containing the pyridazine compound (3) and furametopil;

A composition comprising the present pyridazine compound (4) and bixaphene;
A composition containing the present pyridazine compound (4) and isopyrazam;
A composition containing the pyridazine compound (4) and boscalid;
A composition containing the present pyridazine compound (4) and fluopyram;
A composition comprising the present pyridazine compound (4) and floxapyroxad;
A composition containing the present pyridazine compound (4) and sedaxane;
A composition containing the pyridazine compound (4) and penflufen;
A composition containing the present pyridazine compound (4) and flutolanil;
A composition containing the present pyridazine compound (4) and mepronil;
A composition containing the present pyridazine compound (4) and carboxin;
A composition containing the present pyridazine compound (4) and tifluzamide;
A composition containing the present pyridazine compound (4) and penthiopyrad;
A composition comprising the present pyridazine compound (4) and furametopir;

A composition containing the pyridazine compound (5) and bixaphene;
A composition containing the present pyridazine compound (5) and isopyrazam;
A composition containing the present pyridazine compound (5) and boscalid;
A composition containing the present pyridazine compound (5) and fluopyram;
A composition comprising the present pyridazine compound (5) and fluxapilox;
A composition containing the pyridazine compound (5) and sedaxane;
A composition containing the pyridazine compound (5) and penflufen;
A composition containing the pyridazine compound (5) and flutolanil;
A composition containing the pyridazine compound (5) and mepronil;
A composition containing the present pyridazine compound (5) and carboxin;
A composition containing the present pyridazine compound (5) and tifluzamide;
A composition containing the present pyridazine compound (5) and penthiopyrad;
A composition comprising the present pyridazine compound (5) and furametopil;

A composition comprising the present pyridazine compound (6) and bixaphene;
A composition containing the present pyridazine compound (6) and isopyrazam;
A composition containing the present pyridazine compound (6) and boscalid;
A composition containing the present pyridazine compound (6) and fluopyram;
A composition comprising the present pyridazine compound (6) and floxapyroxad;
A composition containing the pyridazine compound (6) and sedaxane;
A composition containing the pyridazine compound (6) and penflufen;
A composition containing the present pyridazine compound (6) and flutolanil;
A composition comprising the present pyridazine compound (6) and mepronil;
A composition containing the present pyridazine compound (6) and carboxin;
A composition containing the present pyridazine compound (6) and tifluzamide;
A composition containing the present pyridazine compound (6) and penthiopyrad;
A composition comprising the present pyridazine compound (6) and furametopir;

A composition comprising the present pyridazine compound (1) and bixaphene in a weight ratio of the present pyridazine compound (1) /bixafen=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (1) and isopyrazam in a weight ratio of the present pyridazine compound (1) /isopyrazam=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (1) and boscalid in a weight ratio of the present pyridazine compound (1) /boscalid=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (1) and fluopyram in a weight ratio of the present pyridazine compound (1) /fluopyram=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (1) and floxapyroxad in a weight ratio of the present pyridazine compound (1) /fluxapiroxad=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (1) and sedaxane in a weight ratio of the present pyridazine compound (1) /sedaxane=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (1) and penflufen in a weight ratio of the present pyridazine compound (1) /penflufen=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (1) and flutolanil in a weight ratio of the present pyridazine compound (1) /flutranyl=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (1) and mepronil in a weight ratio of the present pyridazine compound (1) /mepronil=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (1) and carboxin in a weight ratio of the present pyridazine compound (1) /carboxyn=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (1) and tifluzamide in a weight ratio of the present pyridazine compound (1) /tifluzamide=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (1) and penthiopyrad at a weight ratio of the present pyridazine compound (1) /pentiopyrad=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (1) and flametopil in a weight ratio of the present pyridazine compound (1) /framethopyl=0.1/1 to 10/1;

A composition comprising the present pyridazine compound (2) and bixafen in a weight ratio of the present pyridazine compound (2) /bixafen=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (2) and isopyrazam in a weight ratio of the present pyridazine compound (2) /isopyrazam=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (2) and boscalid in a weight ratio of the present pyridazine compound (2) /boscalid=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (2) and fluopyram in a weight ratio of the present pyridazine compound (2) /fluopyram=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (2) and floxapyroxad in a weight ratio of the present pyridazine compound (2) /fluxapiroxad=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (2) and sedaxane in a weight ratio of the present pyridazine compound (2) /sedaxane=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (2) and penflufen in a weight ratio of the present pyridazine compound (2) /penflufen=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (2) and flutolanil in a weight ratio of the present pyridazine compound (2) /flutranyl=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (2) and mepronil in a weight ratio of the present pyridazine compound (2) /mepronil=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (2) and carboxin in a weight ratio of the present pyridazine compound (2) /carboxyn=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (2) and tifluzamide in a weight ratio of the present pyridazine compound (2) /tifluzamide=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (2) and penthiopyrad at a weight ratio of the present pyridazine compound (2) /pentiopyrad=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (2) and flametopil in a weight ratio of the present pyridazine compound (2) /framethopyl=0.1/1 to 10/1;

A composition comprising the present pyridazine compound (3) and bixafen in a weight ratio of the present pyridazine compound (3) /bixafen=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (3) and isopyrazam in a weight ratio of the present pyridazine compound (3) /isopyrazam=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (3) and boscalid in a weight ratio of the present pyridazine compound (3) /boscalid=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (3) and fluopyram in a weight ratio of the present pyridazine compound (3) /fluopyram=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (3) and floxapyroxad in a weight ratio of the present pyridazine compound (3) /floxapyroxad=0.1/1 to 10/1;
A composition containing the present pyridazine compound (3) and sedaxane in a weight ratio of the present pyridazine compound (3) /sedaxane=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (3) and penflufen in a weight ratio of the present pyridazine compound (3) /penflufen=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (3) and flutolanil in a weight ratio of the present pyridazine compound (3) /flutranyl=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (3) and mepronil in a weight ratio of the present pyridazine compound (3) /mepronil=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (3) and carboxin in a weight ratio of the present pyridazine compound (3) /carboxyn=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (3) and tifluzamide in a weight ratio of the present pyridazine compound (3) /tifluzamide=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (3) and penthiopyrad at a weight ratio of the present pyridazine compound (3) /pentiopyrad=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (3) and flametopil in a weight ratio of the present pyridazine compound (3) /framethopyl=0.1/1 to 10/1;

A composition comprising the present pyridazine compound (4) and bixaphene in a weight ratio of the present pyridazine compound (4) /bixafen=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (4) and isopyrazam in a weight ratio of the present pyridazine compound (4) /isopyrazam=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (4) and boscalid in a weight ratio of the present pyridazine compound (4) /boscalid=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (4) and fluopyram in a weight ratio of the present pyridazine compound (4) /fluopyram=0.1/1 to 10/1;
A composition containing the present pyridazine compound (4) and floxapyroxad in a weight ratio of the present pyridazine compound (4) /floxapyroxad=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (4) and sedaxane in a weight ratio of the present pyridazine compound (4) /sedaxane=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (4) and penflufen in a weight ratio of the present pyridazine compound (4) /penflufen=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (4) and flutolanil in a weight ratio of the present pyridazine compound (4) /flutranyl=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (4) and mepronil in a weight ratio of the present pyridazine compound (4) /mepronil=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (4) and carboxin in a weight ratio of the present pyridazine compound (4) /carboxyn=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (4) and tifluzamide in a weight ratio of the present pyridazine compound (4) /tifluzamide=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (4) and penthiopyrad at a weight ratio of the present pyridazine compound (4) /pentiopyrad=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (4) and flametopil in a weight ratio of the present pyridazine compound (4) /framethopyl=0.1/1 to 10/1;

A composition comprising the present pyridazine compound (5) and bixaphene in a weight ratio of the present pyridazine compound (5) /bixafen=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (5) and isopyrazam in a weight ratio of the present pyridazine compound (5) /isopyrazam=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (5) and boscalid in a weight ratio of the present pyridazine compound (5) /boscalid=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (5) and fluopyram in a weight ratio of the present pyridazine compound (5) /fluopyram=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (5) and floxapyroxad in a weight ratio of the present pyridazine compound (5) /floxapyroxad=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (5) and sedaxane in a weight ratio of the present pyridazine compound (5) /sedaxane=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (5) and penflufen in a weight ratio of the present pyridazine compound (5) /penflufen=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (5) and flutolanil in a weight ratio of the present pyridazine compound (5) /flutranyl=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (5) and mepronil in a weight ratio of the present pyridazine compound (5) /mepronil=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (5) and carboxin in a weight ratio of the present pyridazine compound (5) /carboxyn=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (5) and tifluzamide in a weight ratio of the present pyridazine compound (5) /tifluzamide=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (5) and penthiopyrad at a weight ratio of the present pyridazine compound (5) /pentiopyrad=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (5) and flametopil in a weight ratio of the present pyridazine compound (5) /framethopyl=0.1/1 to 10/1;

A composition comprising the present pyridazine compound (6) and bixaphene in a weight ratio of the present pyridazine compound (6) /bixafen=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (6) and isopyrazam in a weight ratio of the present pyridazine compound (6) /isopyrazam=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (6) and boscalid in a weight ratio of the present pyridazine compound (6) /boscalid=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (6) and fluopyram in a weight ratio of the present pyridazine compound (6) /fluopyram=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (6) and floxapyroxad in a weight ratio of the present pyridazine compound (6) /floxapyroxad=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (6) and sedaxane in a weight ratio of the present pyridazine compound (6) /sedaxane=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (6) and penflufen in a weight ratio of the present pyridazine compound (6) /penflufen=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (6) and flutolanil in a weight ratio of the present pyridazine compound (6) /flutranyl=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (6) and mepronil in a weight ratio of the present pyridazine compound (6) /mepronil=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (6) and carboxin in a weight ratio of the present pyridazine compound (6) /carboxyn=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (6) and tifluzamide in a weight ratio of the present pyridazine compound (6) /tifluzamide=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (6) and penthiopyrad at a weight ratio of the present pyridazine compound (6) /pentiopyrad=0.1/1 to 10/1;
A composition comprising the present pyridazine compound (6) and flametopil in a weight ratio of the present pyridazine compound (6) /framethopyl=0.1/1 to 10/1.

  The plant disease control method of the present invention (hereinafter referred to as the present invention control method) is carried out by treating an effective amount of the present pyridazine compound and the present carboxamide compound on the plant or the soil where the plant is 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.

  In the control method of the present invention, the pyridazine compound and the carboxamide compound may be treated separately on the plant or the soil where the plant is cultivated at the same time, but usually from the viewpoint of simplicity during the treatment, It is processed.

  In the present control method, examples of the treatment method of the present pyridazine compound and the present carboxamide compound include foliage treatment, soil treatment, root treatment, and seed treatment.

Examples of such foliage treatment include a method of treating the surface of a plant being cultivated by foliage spraying and tree trunk spraying.
Examples of the root treatment include a method of immersing the whole plant or root in a chemical solution containing the pyridazine compound and the carboxamide compound, and a solid preparation containing the pyridazine compound, the carboxamide compound and a solid carrier. The method of making it adhere to the root part of a plant is mentioned.
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. Spray treatment for spraying on the surface or the surface of a bulb, a smearing treatment for applying to a seed or a bulb while adding a small amount of water to the wettable powder, emulsion or flowable of the composition of the present invention, or a solution of the composition of the present invention And dipping treatment for immersing seeds for a certain period of time, film coating treatment and pellet coating treatment.

In the control method of the present invention, the treatment amount of the present pyridazine compound and the present carboxamide compound is the kind of plant to be treated, the kind and occurrence frequency of plant diseases to be controlled, the formulation form, the treatment time, the treatment method, the treatment place, the weather Depending on the conditions, etc., when treated on the foliage of the plant or when treated on the soil cultivating the plant, the total amount of the pyridazine compound and the carboxamide compound is usually 1 to 500 g per 1000 m ² , preferably It is 2 to 200 g, more preferably 10 to 100 g. In addition, the treatment amount of the present pyridazine compound and the present carboxamide compound in the treatment of seeds is the total amount of the present pyridazine compound and the present carboxamide compound, and is usually 0.001 to 10 g, preferably 0.01 to 1 g, per 1 kg of seed. It is.
Emulsions, wettable powders, flowables and the like are usually treated by diluting with water and spraying. In this case, the concentration of the present pyridazine compound and the present carboxamide compound is a total concentration of the present pyridazine compound and the present carboxamide compound, and is usually 0.0005 to 2% by weight, preferably 0.005 to 1% by weight. Powders, granules, etc. are usually processed without dilution.

  Hereinafter, the present invention will be described in more detail with reference to 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.

  First, the manufacture example of this pyridazine compound used for this invention composition is demonstrated.

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１モル／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−ジクロロー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

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 for 4 hours at room temperature. After stirring, the mixture was allowed to stand 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) -4- (4-fluorophenyl). 2.53 g of -5-hydroxy-5-methyl-2 (5H) -furanone was obtained.
¹ H-NMR (CDCl ₃ , TMS) δ (ppm): 1.78 (3H, s), 5.29 (1H, brs), 6.97-7.03 (2H, m), 7.47 -7.51 (2H, m), 7.82 (1H, brs), 8.53 (1H, brs)

Hydrazine monohydrate in 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 Japanese product 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), dried under reduced pressure, and 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)

1.19 g of 4- (3,5-dichloro-2-pyridyl) -5- (4-fluorophenyl) -6-methyl-2H-pyridazin-3-one and 15 g of phosphorus oxychloride 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)

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。重層水で中和した後、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

4- (3,5-dichloro-2-pyridyl) -5- (4-fluorophenyl) -6-methyl-2H-pyridazin-3-one 2.45 g and phosphorus oxybromide 8.0 g were mixed, 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. After neutralizing with multilayer water, 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)

The pyridazine compound (2) 0.85 g, copper cyanide 0.22 g and N, N-dimethylacetamide 6 ml 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)

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。有機層を重層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

This 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 layered water 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)

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６モル／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

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 while heating under reflux. To the reaction mixture was added 35 ml of a 6 mol / L hydrochloric acid aqueous solution under ice-cooling, and the 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)

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１モル／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−ジクロロー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

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 in a water bath, 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 a saturated aqueous sodium bicarbonate solution 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)

0.35 g of hydrazine monohydrate in 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 Then, 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), dried under reduced pressure, and 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-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)

  Next, formulation examples are shown.

Formulation Example 1
2.5 parts of any of the present pyridazine compounds (1) to (6), 1.25 parts of bixaphene, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 76.25 parts of xylene Each formulation is obtained by mixing well.

Formulation Example 2
2.5 parts of any of the present pyridazine compounds (1) to (6), 1.25 parts of isopyrazam, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 76.25 parts of xylene Each formulation is obtained by mixing well.

Formulation Example 3
2.5 parts of any of the present pyridazine compounds (1) to (6), 1.25 parts of boscalid, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 76.25 parts of xylene Each formulation is obtained by mixing well.

Formulation Example 4
2.5 parts of any of the present pyridazine compounds (1) to (6), 1.25 parts of fluopyram, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 76.25 parts of xylene Each formulation is obtained by mixing well.

Formulation Example 5
2.5 parts of any of the present pyridazine compounds (1) to (6), 1.25 parts of floxapyroxide, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate and xylene 76 Each formulation is obtained by mixing well 25 parts.

Formulation Example 6
2.5 parts of any of the present pyridazine compounds (1) to (6), 1.25 parts of sedaxane, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 76.25 parts of xylene Each formulation is obtained by mixing well.

Formulation Example 7
2.5 parts of any of the present pyridazine compounds (1) to (6), 1.25 parts of penflufen, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 76.25 parts of xylene Each formulation is obtained by mixing well.

Formulation Example 8
2.5 parts of any of the present pyridazine compounds (1) to (6), 1.25 parts of flutolanil, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 76.25 parts of xylene Each formulation is obtained by mixing well.

Formulation Example 9
2.5 parts of any of the present pyridazine compounds (1) to (6), 1.25 parts of mepronil, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 76.25 parts of xylene Each formulation is obtained by mixing well.

Formulation Example 10
2.5 parts of any one of the present pyridazine compounds (1) to (6), 1.25 parts of carboxin, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 76.25 of xylene. Each formulation is obtained by mixing the parts well.

Formulation Example 11
2.5 parts of any of the present pyridazine compounds (1) to (6), 1.25 parts of tifluzamide, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 76.25 parts of xylene Each formulation is obtained by mixing well.

Formulation Example 12
2.5 parts of any one of the present pyridazine compounds (1) to (6), 1.25 parts of pentiopyrad, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 76.25 parts of xylene Each formulation is obtained by mixing well.

Formulation Example 13
2.5 parts of any of the present pyridazine compounds (1) to (6), 1.25 parts of furametopyl, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 76.25 parts of xylene Each formulation is obtained by mixing well.

Formulation Example 14
2 parts of any of the present pyridazine compounds (1) to (6), 8 parts of bixaphene, 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and 55 parts of water Each formulation is obtained by mixing and pulverizing by a wet pulverization method.

Formulation Example 15
2 parts of any of the present pyridazine compounds (1) to (6), 8 parts of isopyrazam, 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and 55 parts of water Each formulation is obtained by mixing and pulverizing by a wet pulverization method.

Formulation Example 16
2 parts of any of the present pyridazine compounds (1) to (6), 8 parts of boscalid, 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and 55 parts of water Each formulation is obtained by mixing and pulverizing by a wet pulverization method.

Formulation Example 17
2 parts of any of the present pyridazine compounds (1) to (6), 8 parts of fluopyram, 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and 55 parts of water Each formulation is obtained by mixing and pulverizing by a wet pulverization method.

Formulation Example 18
2 parts of any of the present pyridazine compounds (1) to (6), 8 parts of floxapyroxide, 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and water Each formulation is obtained by mixing 55 parts and pulverizing by a wet pulverization method.

Formulation Example 19
2 parts of any of the present pyridazine compounds (1) to (6), 8 parts of sedaxane, 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and 55 parts of water Each formulation is obtained by mixing and pulverizing by a wet pulverization method.

Formulation Example 20
2 parts of any one of the pyridazine compounds (1) to (6), 8 parts of penflufen, 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and 55 parts of water Each formulation is obtained by mixing and pulverizing by a wet pulverization method.

Formulation Example 21
2 parts of any of the present pyridazine compounds (1) to (6), 8 parts of flutolanil, 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and 55 parts of water Each formulation is obtained by mixing and pulverizing by a wet pulverization method.

Formulation Example 22
2 parts of any of the present pyridazine compounds (1) to (6), 8 parts of mepronil, 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and 55 parts of water Each formulation is obtained by mixing and pulverizing by a wet pulverization method.

Formulation Example 23
2 parts of any of the present pyridazine compounds (1) to (6), 8 parts of carboxin, 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and 55 parts of water Are mixed and pulverized by a wet pulverization method to obtain each preparation.

Formulation Example 24
2 parts of any of the present pyridazine compounds (1) to (6), 8 parts of tifluzamide, 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and 55 parts of water Each formulation is obtained by mixing and pulverizing by a wet pulverization method.

Formulation Example 25
2 parts of any of the present pyridazine compounds (1) to (6), 8 parts of pentiopyrad, 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and 55 parts of water Each formulation is obtained by mixing and pulverizing by a wet pulverization method.

Formulation Example 26
2 parts of any one of the pyridazine compounds (1) to (6), 8 parts of furametopil, 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and 55 parts of water Each formulation is obtained by mixing and pulverizing by a wet pulverization method.

Formulation Example 27
5 parts of any one of the pyridazine compounds (1) to (6), 10 parts of bixaphene, 1.5 parts of sorbitan trioleate and 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol are mixed and wetted. After finely pulverizing by a pulverization method, 45 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added thereto, and further 10 parts of propylene glycol is added and mixed by stirring. Get.

Formulation Example 28
5 parts of any of the present pyridazine compounds (1) to (6), 10 parts of isopyrazam, 1.5 parts of sorbitan trioleate and 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol are mixed and wetted. After finely pulverizing by a pulverization method, 45 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added thereto, and further 10 parts of propylene glycol is added and mixed by stirring. Get.

Formulation Example 29
5 parts of any of the present pyridazine compounds (1) to (6), 10 parts of boscalid, 1.5 parts of sorbitan trioleate and 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol are mixed and wetted. After finely pulverizing by a pulverization method, 45 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added thereto, and further 10 parts of propylene glycol is added and mixed by stirring. Get.

Formulation Example 30
5 parts of any of the present pyridazine compounds (1) to (6), 10 parts of fluopyram, 1.5 parts of sorbitan trioleate and 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol are mixed and wetted. After finely pulverizing by a pulverization method, 45 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added thereto, and further 10 parts of propylene glycol is added and mixed by stirring. Get.

Formulation Example 31
5 parts of any one of the pyridazine compounds (1) to (6), 10 parts of floxapyroxad, 1.5 parts of sorbitan trioleate and 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol are mixed. Then, after finely pulverizing by wet pulverization method, 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. Each formulation is obtained.

Formulation Example 32
5 parts of any of the present pyridazine compounds (1) to (6), 10 parts of sedaxane, 1.5 parts of sorbitan trioleate and 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol are mixed and wet After finely pulverizing by a pulverization method, 45 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added thereto, and further 10 parts of propylene glycol is added and mixed by stirring. Get.

Formulation Example 33
5 parts of any of the present pyridazine compounds (1) to (6), 10 parts of penflufen, 1.5 parts of sorbitan trioleate and 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol are mixed and wetted. After finely pulverizing by a pulverization method, 45 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added thereto, and further 10 parts of propylene glycol is added and mixed by stirring. Get.

Formulation Example 34
5 parts of any of the present pyridazine compounds (1) to (6), 10 parts of flutolanil, 1.5 parts of sorbitan trioleate and 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol are mixed and wetted. After finely pulverizing by a pulverization method, 45 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added thereto, and further 10 parts of propylene glycol is added and mixed by stirring. Get.

Formulation Example 35
5 parts of any one of the pyridazine compounds (1) to (6), 10 parts of mepronil, 1.5 parts of sorbitan trioleate and 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol are mixed and wetted. After finely pulverizing by a pulverization method, 45 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added thereto, and further 10 parts of propylene glycol is added and mixed by stirring. Get.

Formulation Example 36
58.5 of any of the present pyridazine compounds (1) to (6), 10 parts of carboxin, 1.5 parts of sorbitan trioleate and 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol are mixed, After finely pulverizing by a wet pulverization method, 45 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added thereto, and further 10 parts of propylene glycol is added and stirred and mixed. A formulation is obtained.

Formulation Example 37
5 parts of any of the present pyridazine compounds (1) to (6), 10 parts of tifluzamide, 1.5 parts of sorbitan trioleate and 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol are mixed and wetted. After finely pulverizing by a pulverization method, 45 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added thereto, and further 10 parts of propylene glycol is added and mixed by stirring. Get.

Formulation Example 38
5 parts of any of the present pyridazine compounds (1) to (6), 10 parts of pentiopyrad, 1.5 parts of sorbitan trioleate and 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol are mixed and wetted. After finely pulverizing by a pulverization method, 45 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added thereto, and further 10 parts of propylene glycol is added and mixed by stirring. Get.

Formulation Example 39
5 parts of any one of the present pyridazine compounds (1) to (6), 10 parts of furametopil, 1.5 parts of sorbitan trioleate and 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol are mixed and wetted. After finely pulverizing by a pulverization method, 45 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added thereto, and further 10 parts of propylene glycol is added and mixed by stirring. Get.

Formulation Example 40
1 part of any of the present pyridazine compounds (1) to (6), 4 parts of bixaphene, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 62 parts of kaolin clay, After adding water and kneading well, each formulation is obtained by granulating and drying.

Formulation Example 41
1 part of any of the present pyridazine compounds (1) to (6), 4 parts of isopyrazam, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 62 parts of kaolin clay are thoroughly mixed. After adding water and kneading well, each formulation is obtained by granulating and drying.

Formulation Example 42
1 part of any of the present pyridazine compounds (1) to (6), 4 parts of boscalid, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 62 parts of kaolin clay, After adding water and kneading well, each formulation is obtained by granulating and drying.

Formulation Example 43
1 part of any one of the present pyridazine compounds (1) to (6), 4 parts of fluopyram, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 62 parts of kaolin clay are thoroughly mixed. After adding water and kneading well, each formulation is obtained by granulating and drying.

Formulation Example 44
1 part of any one of the pyridazine compounds (1) to (6), 4 parts of floxapyroxide, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 62 parts of kaolin clay After mixing, adding water and kneading well, each formulation is obtained by granulating and drying.

Formulation Example 45
1 part of any of the present pyridazine compounds (1) to (6), 4 parts of sedaxan, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 62 parts of kaolin clay are thoroughly mixed. After adding water and kneading well, each formulation is obtained by granulating and drying.

Formulation Example 46
1 part of any one of the present pyridazine compounds (1) to (6), 4 parts of penflufen, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 62 parts of kaolin clay, After adding water and kneading well, each formulation is obtained by granulating and drying.

Formulation Example 47
1 part of any one of the pyridazine compounds (1) to (6), 4 parts of flutolanil, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 62 parts of kaolin clay, After adding water and kneading well, each formulation is obtained by granulating and drying.

Formulation Example 48
1 part of any of the present pyridazine compounds (1) to (6), 4 parts of mepronil, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 62 parts of kaolin clay, After adding water and kneading well, each formulation is obtained by granulating and drying.

Formulation Example 49
1 part of any of the pyridazine compounds (1) to (6), 4 parts of carboxin, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 62 parts of kaolin clay are thoroughly mixed. After adding water and kneading well, each formulation is obtained by granulating and drying.

Formulation Example 50
1 part of any of the present pyridazine compounds (1) to (6), 4 parts of tifluzamide, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 62 parts of kaolin clay are thoroughly mixed. After adding water and kneading well, each formulation is obtained by granulating and drying.

Formulation Example 51
1 part of any one of the present pyridazine compounds (1) to (6), 4 parts of pentiopyrad, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 62 parts of kaolin clay are thoroughly mixed. After adding water and kneading well, each formulation is obtained by granulating and drying.

Formulation Example 52
1 part of any one of the pyridazine compounds (1) to (6), 4 parts of furametopil, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 62 parts of kaolin clay, After adding water and kneading well, each formulation is obtained by granulating and drying.

Formulation Example 53
1 part of any of the present pyridazine compounds (1) to (6), 4 parts of bixaphene, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 62 parts of kaolin clay, After adding water and kneading well, each formulation is obtained by granulating and drying.

Formulation Example 54
1 part of any of the present pyridazine compounds (1) to (6), 4 parts of isopyrazam, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 62 parts of kaolin clay are thoroughly mixed. After adding water and kneading well, each formulation is obtained by granulating and drying.

Formulation Example 55
12.5 parts of any one of the pyridazine compounds (1) to (6), 37.5 parts of floxapyroxad, 3 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and 45 parts of synthetic hydrous hydroxide Each formulation is obtained by grinding and mixing.

Formulation Example 56
A preparation is obtained by thoroughly pulverizing and mixing 3 parts of any of the present pyridazine compounds (1) to (6), 2 parts of isopyrazam, 85 parts of kaolin clay and 10 parts of talc.

  Next, test examples are shown.

Test example 1
A plastic pot was filled with soil, seeded with wheat (variety: Apogee), 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 Industry) = 5: 1 (volume ratio)) to prepare a preparation, diluted with water to a predetermined concentration, and the diluted solution The foliage was sprayed so as to adhere well 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, it was first placed under high humidity at 18 ° C. for 3 days, then removed from high humidity and cultivated in a constant temperature 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 is referred to 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].

Test example 2
A test compound having a predetermined weight with respect to 10 g of wheat (variety: Shirogane) seeds naturally infected with spores of a red snow rot fungus (Microdocium nivale) using a rotary seed processing machine (seed dresser, manufactured by Hans-Ulrich Hege GmbH) Apply 100 μl of cyclohexanone solution containing
One day after the treatment, the soil is packed in a plastic pot, seeds treated with the test compound are sown, and cultivated in a glass greenhouse for 20 days (this is referred to as a treatment zone). Thereafter, the presence or absence of red snow rot in seedlings sprouting from various offsprings is observed, and the incidence is determined by the following formula (2).
On the other hand, it is cultivated in the same manner as the treated section using the wheat seeds that have not been subjected to the above-mentioned smearing treatment (this is referred to as an untreated section). Then, the disease incidence is obtained in the same manner as in the treatment area.
As a result, in the seedlings budding from the wheat seeds treated with the composition of the present invention, a reduction in the disease incidence is recognized compared to the seedlings in the untreated section.

Claims (5)

Formula (I)

[Where,
R ¹ represents a chlorine atom, a bromine atom, a cyano group, a methyl group or a methoxy group,
R ² represents a fluorine atom or a hydrogen atom,
R ³ represents a halogen atom,
R ⁴ represents a halogen atom, a methoxy group or a hydrogen atom. ]
A pyridazine compound represented by
A plant disease control composition comprising one or more carboxamide compounds selected from the group (A).
Group (A):
A group consisting of bixafen, isopyrazam, boscalid, fluopyram, floxapyroxad, sedaxane, penflufen, flutolanil, mepronyl, carboxin, tifluzamide, pentiopyrad, and furametopir.   The plant disease control composition according to claim 1, wherein the weight ratio of the pyridazine compound to the carboxamide compound is pyridazine compound / carboxamide compound = 0.1 / 1 to 10/1. Formula (I)

[Where,
R ¹ represents a chlorine atom, a bromine atom, a cyano group, a methyl group or a methoxy group,
R ² represents a fluorine atom or a hydrogen atom,
R ³ represents a halogen atom,
R ⁴ represents a halogen atom, a methoxy group or a hydrogen atom. ]
A pyridazine compound represented by
A method for controlling plant diseases, comprising a step of treating an effective amount with one or more carboxamide compounds selected from the group (A) on a plant or soil for growing plants.
Group (A):
A group consisting of bixafen, isopyrazam, boscalid, fluopyram, floxapyroxad, sedaxane, penflufen, flutolanil, mepronyl, carboxin, tifluzamide, pentiopyrad, and furametopir.   The method for controlling plant diseases according to claim 3, wherein the weight ratio of the pyridazine compound to the carboxamide compound is pyridazine compound / carboxamide compound = 0.1 / 1 to 10/1.   The plant disease control method according to 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.