JP2013151432A - Plant disease control composition and application of the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a composition exhibiting a superior controlling effect on plant diseases.SOLUTION: A plant disease control composition exhibiting a superior plant disease controlling effect includes a pyridazine compound represented by the formula (I) (wherein Ris a chlorine atom, a bromine atom, a cyano group, or a methyl group, and Ris a hydrogen atom or a fluorine atom).

Description

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

  Conventionally, many compounds have been developed to control plant diseases and are put into practical use (see, for example, Patent Document 1 and Patent Document 2).

International Publication No. 2005/121104 Pamphlet International Publication No. 2006/001175 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、シアノ基又はメチル基を表し、
Ｒ²は水素原子又はフッ素原子を表す。〕
で示されるピリダジン化合物と、群Ａ〜群Ｆより選ばれる1種以上の化合物とを含有する植物病害防除組成物。
群Ａ；殺菌剤
群Ｂ；殺虫剤
群Ｃ；殺ダニ剤
群Ｄ；殺線虫剤
群Ｅ；薬害軽減剤
群Ｆ；植物生長調節剤
［２］ 式（Ｉ）

〔式中、
Ｒ¹は塩素原子、臭素原子、シアノ基又はメチル基を表し、
Ｒ²は水素原子又はフッ素原子を表す。〕
で示されるピリダジン化合物と、群Ａ〜群Ｆより選ばれる1種以上の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；殺菌剤
群Ｂ；殺虫剤
群Ｃ；殺ダニ剤
群Ｄ；殺線虫剤
群Ｅ；薬害軽減剤
群Ｆ；植物生長調節剤
［３］ 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［２］記載の植物病害防除方法。 As a result of studying to find a composition having an excellent control effect against plant diseases, the present inventor has found that a plant disease control composition containing a pyridazine compound represented by the following formula (I) is suitable for plant diseases. It has been found that it has an excellent control effect 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 or a methyl group,
R ² represents a hydrogen atom or a fluorine atom. ]
The plant disease control composition containing the pyridazine compound shown by these, and 1 or more types of compounds chosen from the group A-group F.
Group A; fungicide group B; insecticide group C; acaricide group D; nematicide group E; safener group F; plant growth regulator [2] Formula (I)

[Where,
R ¹ represents a chlorine atom, a bromine atom, a cyano group or a methyl group,
R ² represents a hydrogen atom or a fluorine atom. ]
The plant disease control method including the process of processing the effective amount of the pyridazine compound shown by these, and 1 or more types of compounds chosen from the group A-the group F to the soil which grows a plant or a plant.
Group A; fungicide group B; insecticide group C; acaricide group D; nematicide group E; safener group F; plant growth regulator [3] plant or plant growing soil is wheat or The plant disease control method according to [2], which is soil for cultivating wheat.

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

〔式中、
Ｒ¹は塩素原子、臭素原子、シアノ基又はメチル基を表し、
Ｒ²は水素原子又はフッ素原子を表す。〕
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。）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)

[Where,
R ¹ represents a chlorine atom, a bromine atom, a cyano group or a methyl group,
R ² represents a hydrogen atom or a fluorine atom. ]
The pyridazine compound (Hereinafter, it describes as this pyridazine compound.) Shown by these.

As an aspect of this pyridazine compound used for this invention composition, the following pyridazine compounds are mentioned, for example.
A pyridazine compound represented by formula (I), wherein R ¹ is a chlorine atom or a methyl 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 ¹ is a cyano group;
A pyridazine compound represented by formula (I), wherein R ² is a hydrogen atom;
A pyridazine compound represented by formula (I), wherein R ² is a fluorine atom;
A pyridazine compound represented by formula (I), wherein R ¹ is a chlorine atom, a cyano group or a methyl group, and R ² is a hydrogen atom;
A pyridazine compound represented by formula (I), wherein R ¹ is a chlorine atom, a cyano group or a methyl group, and R ² is a fluorine atom.

Specific examples of the pyridazine compound include the following.
A pyridazine compound in which R ¹ is a chlorine atom and R ² is a hydrogen atom in formula (I) (hereinafter referred to as the present pyridazine compound (1));
A pyridazine compound in which R ¹ is a bromine atom and R ² is a hydrogen atom in formula (I) (hereinafter referred to as the present pyridazine compound (2));
A pyridazine compound in which R ¹ is a cyano group and R ² is a hydrogen atom in formula (I) (hereinafter referred to as the present pyridazine compound (3));
A pyridazine compound in which R ¹ is a methyl group and R ² is a hydrogen atom in formula (I) (hereinafter referred to as the present pyridazine compound (4));
In formula (I), R ¹ is a chlorine atom, and R ² is a fluorine atom (hereinafter referred to as the present pyridazine compound (5));
A pyridazine compound in which R ¹ is a bromine atom and R ² is a fluorine atom in formula (I) (hereinafter referred to as the present pyridazine compound (6));
In formula (I), R ¹ is a cyano group and R ² is a fluorine atom (hereinafter referred to as the present pyridazine compound (7));
A pyridazine compound in which R ¹ is a methyl group and R ² is a fluorine atom in the formula (I) (hereinafter referred to as the present pyridazine compound (8)).

Among the pyridazine compounds, a pyridazine compound in which R ¹ is a chlorine atom or a bromine atom in formula (I) can be produced, for example, by the method described in International Publication No. 2005/121104.

Among the pyridazine compounds, a pyridazine compound in which R ¹ is a methyl group in formula (I) can be produced by the method described in International Publication No. 2006/001175.

〔式中、Ｒ²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、反応混合物を水と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。単離された化合物（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 (I) in which R ¹ is a bromine atom in formula (I). -1) can be produced by reacting with copper cyanide.

[Wherein R ² represents 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, and the filtrate is separated. The obtained organic layer is further washed with water, dried, concentrated, and the like. Compound (I-2) can be isolated. The 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。該反応に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 formula (I) is the compound (I-3) in which R ¹ is a chlorine atom among the pyridazine compounds. 2)

[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 represents 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 in the reaction is usually 0.01 to 0.3 mol with respect to 1 mol of the 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.

  In the composition of the present invention, the pyridazine compound is mixed with a solid carrier, a liquid carrier, a gas carrier, a surfactant and the like, and if necessary, an auxiliary for formulation such as a fixing agent, a dispersant, a stabilizer and the like is added, and water is added. It is formulated into a powder, wettable powder, flowable powder, granule, dry flowable powder, emulsion, aqueous liquid, oil, smoke, aerosol, microcapsule and the like. These preparations contain the present pyridazine compound in a weight ratio of usually 0.1 to 99%, preferably 0.2 to 90%.

  Examples of the solid carrier include clays (for example, kaolin, diatomaceous earth, synthetic hydrous silicon oxide, fusami clay, bentonite, acidic clay), talc, and other inorganic minerals (for example, sericite, quartz powder, sulfur powder, activated carbon, Examples of the liquid carrier include water, alcohols (for example, methanol, ethanol), ketones (for example, acetone, methyl ethyl ketone), aromatic carbonization, and the like. Hydrogens (eg, benzene, toluene, xylene, ethylbenzene, methylnaphthalene), aliphatic hydrocarbons (eg, n-hexane, cyclohexanone, kerosene), esters (eg, ethyl acetate, butyl acetate), nitriles (eg, , Acetonitrile, isobutylnitrile), ethers (eg , Dioxane, diisopropyl ether), acid amides (e.g., dimethylformamide, dimethylacetamide), halogenated hydrocarbons (e.g., dichloroethane, trichlorethylene, and carbon tetrachloride), and the like.

  Examples of the surfactant include alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and polyoxyethylene compounds thereof, polyoxyethylene glycol ethers, polyhydric alcohol esters, sugar alcohol derivatives. Etc.

  Other formulation adjuvants include, for example, fixing agents and dispersants, specifically casein, gelatin, polysaccharides (eg starch, arabic gum, cellulose derivatives, alginic acid), lignin derivatives, bentonite, saccharides, synthetic water-soluble high Molecules (for example, polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids), PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (2-tert-butyl-4) -Mixtures of methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oils, mineral oils, fatty acids or esters thereof.

  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: 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 (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 polysora) 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 phytophathoropathy
Diseases of apples: Monilia mary, rot (Valsa ceratosperma), powdery mildew (Podospataera leukotrica), spotted leaf disease (Alternaria altanatal pest disease) , Phytophactora catorum.
Pear diseases: Venturia nashicola, V. pirina, Black spot (Alternaria alternata Japan pearpathotype), Red scab (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 warp (Fusarium oxysporum), por disease (u) ), 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 Diseases: Rhizoctonia solani caused by Rhizoctonia spp., Mildew fungus (Mycosphaerella areola), Black rot rot disease (Thielaviopsis basis caused by Thielaviopsis spp.).
Coffee disease: Rust (Hemileia vastatrix).
Diseases of sugarcane: rust (Puccinia melanocephela, Puccinia küehnii), smut (Ustilago scitamine).
Sunflower Disease: Rust (Puccinia helianthi).
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. (Pythium aphanidermatum, P. debarianum, P. gramicola, P. irregulare, P. ultimum), gray mold (Botrytis cinereum), roe 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, Penicillium, Fusarium, Gibberella, Tricoderma, Thielaviopsis, Rhizopus, Mucor, Corticium, Poma, and Rhizoctonia 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 bred by a hybrid technique.

That is, a plant bred by hybrid technology is a plant having hybrid characteristics (generally resulting in increased yield potential, improved resistance to biological and abiotic stress factors, etc.).

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

For example, the “plant” includes HPPD inhibitors such as isoxaflutol, ALS inhibitors such as imazetapyr and thifensulfuronmethyl, EPSP synthase inhibitors, glutamine synthase inhibitors, herbicides such as bromoxynil and dicamba. Also included is a plant to which resistance to is imparted by classical breeding methods or genetic engineering techniques.
As an example of a “plant” to which tolerance has been imparted by a classic breeding method, imidazolinone herbicide-resistant Clearfield (registered trademark) canola, such as imazetapir, and sulfonylurea-based ALS-inhibiting herbicide resistance such as thifensulfuron methyl There are STS soybeans. Examples of “plants” to which tolerance has been imparted by genetic recombination technology include glyphosate and glufosinate-resistant corn, soybean, cotton, rapeseed varieties, RoundupReady (registered trademark), RoundupReady2 (registered trademark) and LibertyLink ( It is already sold under the trade name such as registered trademark.

The “plant” includes a plant that can synthesize, for example, a selective toxin known in the genus Bacillus, using a gene recombination technique.
Toxins expressed in such genetically modified plants include insecticidal proteins from Bacillus cereus and Bacillus popilie; Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C from Bacillus thuringiensis Insecticidal proteins such as δ-endotoxin, VIP1, VIP2, VIP3 or VIP3A; nematicidal insecticidal proteins; toxins produced by animals such as scorpion toxin, spider toxin, bee toxin or insect-specific neurotoxin; filamentous fungal toxins; plants Lectin; Agglutinin; Protease inhibitor such as trypsin inhibitor, serine protease inhibitor, patatin, cystatin, papain inhibitor; Ribosome inactivating protein (RIP) such as lysine, corn-RIP, abrin, ruffin, saporin, bryodin; 3-hydroxysteroid oxidase, ecdysteroid Steroid metabolic enzymes such as UDP-glucosyltransferase and cholesterol oxidase; ecdysone inhibitor; HMG-COA reductase; ion channel inhibitor such as sodium channel and calcium channel inhibitor; juvenile hormone esterase; diuretic hormone receptor; stilbene synthase; Benzyl synthase; chitinase; glucanase and the like.
Moreover, as toxins expressed in such transgenic plants, Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, δ-endotoxin proteins such as Cry3Bb1 or Cry9C, and insecticidal protein hybrids such as VIP1, VIP2, VIP3 or VIP3A Toxins, partially defective toxins, modified toxins are also included. Hybrid toxins are produced by new combinations of different domains of these proteins using recombinant techniques. As a toxin lacking a part, Cry1Ab lacking a part of the amino acid sequence is known. In the modified toxin, one or more amino acids of the natural toxin are substituted.
Examples of these toxins and recombinant plants capable of synthesizing these toxins are EP-A-0 374 753, WO 93/07278, WO 95/34656, EP-A-0 427 529, EP-A-451 878. , WO 03/052073 and the like.
The toxins contained in these recombinant plants particularly confer resistance to Coleoptera pests, Diptera pests, and Lepidoptera pests.

  In addition, genetically modified plants that contain one or more insecticidal pest resistance genes and express one or more toxins are already known, and some are commercially available. Examples of these transgenic plants include YieldGard® (a corn variety expressing Cry1Ab toxin), YieldGard Rootworm® (a corn variety expressing Cry3Bb1 toxin), YieldGard Plus® (Cry1Ab and Cry3Bb1 Corn varieties that express toxins), Herculex I® (corn varieties that express phosphinotricin N-astilyltransferase (PAT) to confer resistance to Cry1Fa2 toxin and glufosinate), NuCOTN33B (Cry1Ac toxin) Cotton varieties expressing), Bollgard I (registered trademark) (cotton varieties expressing Cry1Ac toxin), Bollgard II (registered trademark) (cotton varieties expressing Cry1Ac and Cry2Ab toxin), VIPCOT (registered trademark) (VIP toxin) Cotton varieties), NewLeaf (registered trademark) (potato varieties expressing Cry3A toxin), NatureGard (registered trademark) Agrisure (registered trademark) GT Advant Examples include age (GA21 glyphosate resistance trait), Agrisure (registered trademark) CB Advantage (Bt11 corn borer (CB) trait), Protecta (registered trademark), and the like.

The “plant” includes those imparted with an ability to produce an anti-pathogenic substance having a selective action using a gene recombination technique.
PR proteins and the like are known as examples of anti-pathogenic substances (PRPs, EP-A-0 392 225). Such anti-pathogenic substances and genetically modified plants that produce them are described in EP-A-0 392 225, WO 95/33818, EP-A-0 353 191 and the like.
Examples of anti-pathogenic substances expressed in such genetically modified plants include, for example, sodium channel inhibitors and calcium channel inhibitors (KP1, KP4, KP6 toxins produced by viruses, etc.) are known. Ion channel inhibitors; stilbene synthase; bibenzyl synthase; chitinase; glucanase; PR protein; peptide antibiotics, heterocyclic antibiotics, protein factors involved in plant disease resistance (called plant disease resistance genes, WO No. 03/000906)) and other anti-pathogenic substances produced by microorganisms.

Moreover, the above-mentioned “plant” is a line to which two or more traits relating to herbicide resistance, pest resistance, disease resistance, etc. as described above are imparted using classical breeding techniques or genetic recombination techniques, Also included are strains to which two or more properties of the parent strain are imparted by crossing genetically modified plants having similar or different properties. Examples of such plants include Smart stax (registered trademark).

Depending on the plant species or plant varieties, their growth location and growth conditions (soil, climate, growth season, nutrient), treatment of the composition of the present invention improves plant growth, increases resistance to high or low temperatures, drought Or increased tolerance to salt in water or soil, improved flowering ability, improved harvestability, promoted maturity, increased yield, increased fruit size, increased plant height, leaves Improved green color, faster flowering, improved quality of harvested products and / or increased nutritional value, increased sugar content in fruits, improved storage stability and / or processability of harvested products Improvements may be possible.

  The composition of the present invention is obtained by mixing or mixing the present pyridazine compound with a fungicide, insecticide, acaricide, nematicide, safener, herbicide, plant growth regulator, fertilizer or soil conditioner. Can be used simultaneously.

（１１）その他の殺菌剤または植物病害防除剤
ジエトフェンカルブ、チウラム、フルアジナム、マンコゼブ、クロロタロニル、キャプタン、ジクロフルアニド、フォルペット、キノキシフェン、フェンヘキサミド、ファモキサドン、フェナミドン、ゾキサミド、エタボキサム、アミスルブロム、シアゾファミド、メトラフェノン、ピリオフェノン、シフルフェナミド、プロキナジド、フルスルファミド、フルオピコリド、フォセチル、シモキサニル、ペンシクロン、トルクロホスメチル、カルプロパミド、ジクロシメット、フェノキサニル、トリシクラゾール、ピロキロン、プロベナゾール、イソチアニル、チアジニル、テブフロキン、ジクロメジン、カスガマイシン、フェリムゾン、フサライド、バリダマイシン、ヒドロキシイソキサゾール、イミノクタジン酢酸塩、イソプロチオラン、オキソリニック酸、オキシテトラサイクリン、ストレプトマイシン、塩基性塩化銅、水酸化第二銅、塩基性硫酸銅、有機銅、硫黄、、アメトクトラジン、フェンピラザミン、下記式（ｂ）で表される化合物；

下記式（ｃ）で表される化合物；

下記式（ｄ）で表される化合物；

下記式（ｅ）で表される化合物；

等が挙げられる。
The fungicides described in group A include, for example, the azole fungicides propiconazole, prothioconazole, triadimenol, prochloraz, penconazole, teconazole, teconazole and teconazole. ), Flusilazole, diniconazole, bromconazole, epoxiconazole, difenoconazole, cyproconazole, cyproconazole, cyproconazole, and cyproconazole. triflumazole, tetraconazole, microbutanil, fenbuconazole, hexaconazole, fluquinconazole, fluconconazole, tricontazole, fluconconazole. Imazaril, flutriafol, simeconazole, ipconazole and the like;
Amine fungicides fenpropimorph, tridemorph, fenpropidin, spiroxamine, etc .;
Benzimidazole fungicides carbendazim, benomyl, thiabendazole, thiophanate-methyl, etc .;
Dicarboximide fungicides procymidone, iprodione, vinclozolin and the like;
Anilinopyrimidine fungicides cyprodinil, pyrimethanil, mepanipyrim and the like;
Phenylpyrrole fungicides fenpiclonil, fludioxonil and the like;
The strobilurin fungicides cresoxim-methyl, azoxystrobin, trifloxystrobin, floxastrobin, picoxystrobin, piroxystrobin, piraxystrobi Dimoxystrobin, pyribencarb, metminostrobin, oryzatrobin, enestrobin, pyramethostrobin, pyroxystrobin, pyroxystrobin, pyroxystrobin in), N-methyl -α- methoxyimino-2 - [(2,5-dimethylphenoxy) methyl] phenylacetamide, and the like;
Acylalanine-based fungicides metalaxyl, metalaxyl M or mefenoxam (benaxyl), benalaxyl M or venaxyl-M orkilax;
Carboxylic acid amide fungicides dimethomorph, iprovalicalb, benchavaricarb-isopropyl, mandipropamide, varifenalate, varifenate, etc.
(10) SDHI fungicides carboxin, mepronil, flutolanil, thifluzamide, furamethpyr, boscalid, penthiopurapipyramid ), Penflufen, sedaxane, isopyrazam, floxapyroxad, a compound represented by the following formula (a), etc .;

(11) Other fungicides or plant disease control agents dietofencarb, thiuram, fluazinam, mancozeb, chlorothalonil, captan, diclofluanid, phorpet, quinoxyphene, fenhexamide, famoxadone, fenamidone, zoxamide, ethaboxam, amisulbrom, cyazofamide, metolafenone , Pyriophenone, cyflufenamide, proquinazide, fursulfamide, flupicolide, fosetil, simoxanyl, pencyclon, toluclophosmethyl, carpropamide, diclocimet, phenoxanyl, tricyclazole, pyroxylone, probenazole, isothianyl, thiazinyl, tebufrodamine, diclofedamine Kisazo , Iminotadine acetate, isoprothiolane, oxolinic acid, oxytetracycline, streptomycin, basic copper chloride, cupric hydroxide, basic copper sulfate, organic copper, sulfur, amethoctrazine, fenpyrazamine, represented by the following formula (b) Compound;

A compound represented by the following formula (c);

A compound represented by the following formula (d);

A compound represented by the following formula (e);

Etc.

Examples of the insecticides described in Group B include (1) organophosphorus compounds such as acephate, aluminum phosphide, butathiofos, cadusafos, chlorethoxyphos, chlor Fenvinphos, chlorpyrifos, chloropyrifos-methyl, cyanophos: CYAP, diazinon, dipodithiophene hlorvos: DDVP), dimethoate, dimethylvinphos, disulfoton, EPN, ethion, etioprofos, etrimfos, fenthion MP MEP), fothiazate, formothion, hydrogen phosphide, isofenphos, isoxathion, malathion, mesulfenfos (mesulfenthios) thidathion (DMTP), monocrotophos, monored (BRP), oxydeprofos (ESP), parathion, fosarone, phosmet (PMP), pyrimiphosmethyl (pirimithmethyl) , Pyridafenthion, quinalphos, phentoate (PAP), profenofos, propopafos, prothiofos (pyrthiophos), pyrachlorfos (pyraclophos) rofos, tebupyrimfos, temefos, tetrachlorvinphos, terbufos, thiomethon, trichlorfon (DE), amidthione (v) cadusafos) and the like;

(2) Carbamate compounds alaniccarb, bendiocarb, benfuracarb, BPMC, carbaryl, carbofuran, carbothofen, carbotophene ), Fenobucarb, phenothiocarb, phenoxycarb, furathiocarb, isoprocarb (MIPC), metocarbyl, metolcarb thiocarb), NAC, oxamyl (oxamyl), pirimicarb (pirimicarb), propoxur (propoxur: PHC), XMC, thiodicarb (thiodicarb), xylylcarb (xylylcarb), aldicarb (aldicarb) or the like;

(3) Synthetic pyrethroid compounds Acrinathrin, Allethrin, Benfluthrin, Beta-Cyfluthrin, Bifenthrin, Cycloprothrin, Cycloprothrin (Cycloprothrin) cyhalothrin, cypermethrin, deltamethrin, esfenvalerate, etofenprox, fenpropratrin, fenvalerate, fenvalate (Flucythrinate), flufenprox, flumethrin, fluvalinate, halfenprox, imiprothrin, permethrin, praretrin, praletrin. (Resmethrin), sigma-cypermethrin, silaflufen, tefluthrin, tralomethrin, transfluthrin, tetrartrin methrin), phenothrin, cyphenothrin, alpha-cypermethrin, zeta-cypermethrin, lambda cithalthrin (lambda-thalmethrin) (Tau-flavinate), 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl (EZ)-(1RS, 3RS; 1RS, 3SR) -2,2-dimethyl-3-prop-1- Enylcyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4-methylbenzyl (EZ)-(1RS, 3RS; 1RS, 3SR) -2,2-dimethyl -3-prop-1-enylcyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl (1RS, 3RS; 1RS, 3SR) -2,2-dimethyl-3- ( 2-methyl-1-propenyl) cyclopropanecarboxylate and the like;

(4) Nereistoxin compounds Cartap, bensultap, thiocyclam, monosultap, bisultap, etc .;

(5) Neonicotinoid compounds Imidacloprid, nitenpyram, acetamiprid, thiamethoxam, thiacloprid, dinoteurine, dinotefur

(6) Benzoylurea compounds Chlorfluazuron, bistrifluron, diafenthiuron, diflubenzuron, fluazuron, flucycloxuron, flucycloxuron Sulfuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, triflumuron, etc.

(7) Phenylpyrazole compounds Acetoprole, etiprole, fipronil, vaniliprole, pyriprole, pyrafluprole, etc .;
(8) Bt toxin insecticide, live spores and produced crystal toxins derived from Bacillus thuringiensis, and mixtures thereof;
(9) Hydrazine-based compounds Chromafenozide, halofenozide, methoxyphenozide, tebufenozide and the like;
(10) Organochlorine compounds Aldrin, dieldrin, dienochlor, endosulfan, methoxychlor and the like;
(11) Natural insecticide machine oil, nicotine sulfate (nicotine-sulfate);

(12) Other insecticides avermectin (vermectin-B), bromopropyrate, buprofezin, chlorphenapyr, cyromazine, benzo (p), benzo (p) emamectin-benzoate, abamectin, fenazaquin, flupyrazofos, hydroprene, metoprene, indoxacarbine, indoxacarbine mycin-A), pymetrozine, pyridalyl, pyriproxyfen, spinosad, sulfuramid, tolfenpyram, piramidene, fluzemide lepilectin, Arsenic acid, Benclothiaz, Calcium cyanamide, Calcium polysulfide, Chlordane, DT, DSP, flune flonicamid, flurimfen, formatenate, metham-ammonium, metham-sodium, methyl bromide, nidinotefuran (ninototefuric acid) oleate, protrifen bute, spiromesifen, sulfur, metaflumizone, spirotetramat, pyrifluetramone, pyrifluin Chrantraniliprole, cyantraniprole
, Sulfoxaflor, flometoquin, flupiradifurone, etc .;

Is mentioned.

  Examples of acaricides (acaricidal active ingredients) described in Group C include, for example, acequinocyl, amitraz, benzoximate, bifenate, phenisobromolate, quinomethioate, and quinomethioate. (Chinomethionat), Chlorbenzilate, CPCBS (Chlorfenson), Clofentezine, Cyflumetofen, Cyclomethofen, thiodefine, xoxentin rb), fenpyroximate, fluacrylpyrim, fluproxyfen, hexythiazox, propargite (di), polynactin complex (py) (Tebufenpyrad), tetradiphon, spirodiclofen, spiromesifen, spirotetramat, amidoflumet, cyenopyrafen (cy) nopyrafen), and the like.

  Examples of the nematicide (nematicidal active ingredient) described in Group D include DCIP, fosthiazate, levamisole hydrochloride, methylisothiocyanate, morantel tartarate, and imisiaphos. (Imicyafos), flufensulfone and the like.

  Examples of the safeners (phytotoxicity-reducing active ingredients) described in Group E include, for example, 1,8-naphthalic hydride, chometrinyl, oxabetrilin, fluxofenin ( fluxofenim, flurazole, benoxacor, dichlormid, furilazole, fenchlorim, daimulon, cumyluronate, cumyluronate -Mexyl), fenchlorazole ethi (Fenchlorazole-ethyl), mefenpyr-diethyl (mefenpyr-diethyl), isoxadifen-ethyl (isoxadifen-ethyl), 4- oxo-4 - [(2-phenylethyl) amino] - butyric acid, and the like.

  Examples of plant growth regulators (plant growth regulation active ingredients) described in group F include etephon, chlormequat-chloride, mepiquat-chloride, and the like.

  These other fungicides, insecticides, acaricides, nematicides, safeners, herbicides, plant growth regulators and the like that can be included in the composition of the present invention can be 0 to 6 acceptable. .

  As the plant disease control method of the present invention (hereinafter referred to as the present invention control method), an effective amount of the present pyridazine compound and one or more compounds selected from groups A to F is applied to the plant or the soil where the plant is cultivated. Processing. 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 one or more compounds selected from the groups A to F may be treated separately in the same period on the plant or the soil where the plant is cultivated. From the point of view, it is processed as the composition of the present invention.

  In the control method of the present invention, the mixing ratio of the present pyridazine compound and one or more compounds selected from Group A to Group F is the type of plant to be treated, the type and frequency of occurrence of plant diseases to be controlled, and the formulation form Depending on the treatment time, treatment method, treatment location, weather conditions, etc., when treating to the foliage of plants or when treating to the soil cultivating plants, the compounds contained in group A Regardless of the presence or absence of the present pyridazine compound / one or more compounds selected from group A = 1/100 to 100/1, the compounds included in group B are from the present pyridazine compound / group B regardless of the presence or absence of other components. One or more compounds selected = 1/100 to 1/1, and for compounds included in Group C, one or more compounds selected from the present pyridazine compound / Group C regardless of the presence or absence of other components = 1/1 For compounds contained in 00 to 1/1, group D, one or more compounds selected from the present pyridazine compound / group D regardless of the presence or absence of other components = 1/100 to 1/1, contained in group E For compounds, one or more compounds selected from the present pyridazine compound / group E, regardless of the presence or absence of other components = 1/100 to 10/1, and for compounds included in group F, regardless of the presence or absence of other components One or more compounds selected from the present pyridazine compound / group F = 1/100 to 10/1.

By treating the composition of the present invention with a herbicide-tolerant crop by some method and treating certain herbicides at the same time or at different times, the effect of improving crop growth can be effectively and labor-saving. Can also be obtained. Here, the “crop growth improvement effect” means that the crop yield is increased as a result of controlling insect damage, disease, weed damage, and the like.
Specifically, crops imparted with imidazolinone herbicide resistance, such as Clearfield (registered trademark) canola, are treated with the composition of the present invention and an imidazolinone herbicide such as imazapyr at the same time or at different times. Canola growth can be improved. In addition, crops imparted with glyphosate tolerance such as Roundup Ready (registered trademark) cotton and Roundup Ready 2 soybean (registered trademark) are treated with the composition of the present invention and glyphosate at the same time or at different times to increase the growth of Roundup Ready cotton and Roundup Ready 2 soybean It can be improved. In addition, the growth of LibertyLink corn can be improved by treating the crop imparted with glufosinate tolerance, for example, LibertyLink (registered trademark) corn, with the composition of the present invention and glufosinate at the same time or at different times.

As an aspect of this invention composition, the following are mentioned, for example.

A composition comprising the present pyridazine compound (1), clothianidin, ethaboxam, metalaxyl and ipconazole;
A composition comprising the present pyridazine compound (1), clothianidin, ethaboxam, metalaxyl M, and N-methyl-α-methoxyimino-2-[(2,5-dimethylphenoxy) methyl] phenylacetamide;
A composition containing the present pyridazine compound (1), clothianidin, ethaboxam, metalaxyl and tolcrofosmethyl;
A composition comprising the present pyridazine compound (1), clothianidin, ethaboxam, metalaxyl M, and metconazole;
A composition comprising the present pyridazine compound (1), clothianidin, ethaboxam, metalaxyl M and 4-oxo-4-[(2-phenylethyl) amino] -butyric acid;
A composition comprising the present pyridazine compound (1), clothianidin, ethaboxam, metalaxyl M and fludioxonil;
A composition comprising the present pyridazine compound (1), imidacloprid, ethaboxam, metalaxyl and ipconazole;
A composition comprising the present pyridazine compound (1), imidacloprid, ethaboxam, metalaxyl M, and N-methyl-α-methoxyimino-2-[(2,5-dimethylphenoxy) methyl] phenylacetamide;
A composition comprising the present pyridazine compound (1), imidacloprid, ethaboxam, metalaxyl and tolcrofosmethyl;
A composition containing the present pyridazine compound (1), imidacloprid, ethaboxam, metalaxyl M, and metconazole;
A composition comprising the present pyridazine compound (1), imidacloprid, ethaboxam, metalaxyl M and 4-oxo-4-[(2-phenylethyl) amino] -butyric acid;
A composition comprising the present pyridazine compound (1), imidacloprid, ethaboxam, metalaxyl M and fludioxonil;
A composition comprising the present pyridazine compound (3), clothianidin, ethaboxam, metalaxyl and ipconazole;
A composition comprising the present pyridazine compound (3), clothianidin, ethaboxam, metalaxyl M, and N-methyl-α-methoxyimino-2-[(2,5-dimethylphenoxy) methyl] phenylacetamide;
A composition comprising the present pyridazine compound (3), clothianidin, ethaboxam, metalaxyl and tolcrofosmethyl;
A composition comprising the present pyridazine compound (3), clothianidin, ethaboxam, metalaxyl M, and metconazole;
A composition comprising the present pyridazine compound (3), clothianidin, ethaboxam, metalaxyl M and 4-oxo-4-[(2-phenylethyl) amino] -butyric acid;
A composition comprising the present pyridazine compound (3), clothianidin, ethaboxam, metalaxyl M and fludioxonil;
A composition comprising the present pyridazine compound (3), imidacloprid, ethaboxam, metalaxyl and ipconazole;
A composition comprising the present pyridazine compound (3), imidacloprid, ethaboxam, metalaxyl M, and N-methyl-α-methoxyimino-2-[(2,5-dimethylphenoxy) methyl] phenylacetamide;
A composition containing the present pyridazine compound (3), imidacloprid, ethaboxam, metalaxyl and tolcrofosmethyl;
A composition comprising the present pyridazine compound (3), imidacloprid, ethaboxam, metalaxyl M, and metconazole;
A composition comprising the present pyridazine compound (3), imidacloprid, ethaboxam, metalaxyl M and 4-oxo-4-[(2-phenylethyl) amino] -butyric acid;
A composition comprising the present pyridazine compound (3), imidacloprid, ethaboxam, metalaxyl M and fludioxonil;

A composition comprising the present pyridazine compound (1), clothianidin, ethaboxam, metalaxyl, 4-oxo-4-[(2-phenylethyl) amino] -butyric acid and fludioxonil;
A composition comprising the present pyridazine compound (1), imidacloprid, ethaboxam, metalaxyl, 4-oxo-4-[(2-phenylethyl) amino] -butyric acid and fludioxonil;
A composition comprising the present pyridazine compound (3), clothianidin, ethaboxam, metalaxyl, 4-oxo-4-[(2-phenylethyl) amino] -butyric acid and fludioxonil;
A composition comprising the present pyridazine compound (1), imidacloprid, ethaboxam, metalaxyl, 4-oxo-4-[(2-phenylethyl) amino] -butyric acid and fludioxonil;

  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, formulation examples are shown.

Formulation Example 1

Formulation Example 1
2.5 parts of any of the present pyridazine compounds (1) to (8), 1.25 parts of sulfoxafurol, 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 2
2.5 parts of any of the present pyridazine compounds (1) to (8), 1.25 parts of mancozeb, 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 3
2.5 parts of any of the present pyridazine compounds (1) to (8), 1.25 parts of chlorothalonil, 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 4
2.5 parts of any of the present pyridazine compounds (1) to (8), 1.25 parts of benomyl, 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 (8), 1.25 parts of dicrosimet, 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 6
2.5 parts of any one of the present pyridazine compounds (1) to (8), 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 7
2.5 parts of any of the present pyridazine compounds (1) to (8), 1.25 parts of ferrimzone, 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 (8), 1.25 parts of validamycin, 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 (8), 1.25 parts of dietofencarb, 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 (8), 1.25 parts of tolcrofosmethyl, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 76.25 xylene Each formulation is obtained by mixing the parts well.

Formulation Example 11
2.5 parts of any one of the present pyridazine compounds (1) to (8), 1.25 parts of 4-oxo-4-[(2-phenylethyl) amino] -butyric acid, polyoxyethylene styrylphenyl ether Each formulation is obtained by thoroughly mixing 14 parts, 6 parts calcium dodecylbenzenesulfonate and 76.25 parts xylene.

Formulation Example 12
2.5 parts of any one of the present pyridazine compounds (1) to (8), 1.25 parts of N-methyl-α-methoxyimino-2-[(2,5-dimethylphenoxy) methyl] phenylacetamide, poly Each formulation is obtained by thoroughly mixing 14 parts of oxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 76.25 parts of xylene.

Formulation Example 13
2.5 parts of any of the present pyridazine compounds (1) to (8), 1.25 parts of procymidone, 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 14
2.5 parts of any of the present pyridazine compounds (1) to (8), 1.25 parts of thiodicarb, 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 15
2.5 parts of any of the present pyridazine compounds (1) to (8), 1.25 parts of carbofuran, 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 16
2.5 parts of any of the present pyridazine compounds (1) to (8), 1.25 parts of fludioxonil, 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 17
2 parts of any of the present pyridazine compounds (1) to (8), 8 parts of sulfoxafur, 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 18
2 parts of any of the present pyridazine compounds (1) to (8), 8 parts of mancozeb, 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 19
2 parts of any of the present pyridazine compounds (1) to (8), 8 parts of chlorothalonil, 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and 55 parts of water Each formulation is obtained by mixing and pulverizing by a wet pulverization method.

Formulation Example 20
2 parts of any of the present pyridazine compounds (1) to (8), 8 parts of benomyl, 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 (8), 8 parts of dicrosimet, 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 (8), 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 23
2 parts of any of the present pyridazine compounds (1) to (8), 8 parts of ferrimzone, 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 24
2 parts of any of the present pyridazine compounds (1) to (8), 8 parts of validamycin, 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 (8), 8 parts of dietofencarb, 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and 55 parts of water Each formulation is obtained by mixing and pulverizing by a wet pulverization method.

Formulation Example 26
2 parts of any of the present pyridazine compounds (1) to (8), 8 parts of torquelophosmethyl, 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 27
2 parts of any of the present pyridazine compounds (1) to (8), 8 parts of 4-oxo-4-[(2-phenylethyl) amino] -butyric acid, white carbon and polyoxyethylene alkyl ether sulfate ammonium salt Each formulation is obtained by mixing 35 parts of a mixture (weight ratio 1: 1) and 55 parts of water and finely pulverizing them by a wet pulverization method.

Formulation Example 28
2 parts of any of the present pyridazine compounds (1) to (8), 8 parts of metconazole, 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 29
2 parts of any of the present pyridazine compounds (1) to (8), 8 parts of procymidone, 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 30
2 parts of any of the present pyridazine compounds (1) to (8), 8 parts of thiodicarb, 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 31
2 parts of any of the present pyridazine compounds (1) to (8), 8 parts of carbofuran, 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 32
2 parts of any of the present pyridazine compounds (1) to (8), 8 parts of fludioxonil, 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 33
5 parts of any of the pyridazine compounds (1) to (8), 10 parts of sulfoxafur, 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 34
5 parts of any of the present pyridazine compounds (1) to (8), 10 parts of mancozeb, 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 of the present pyridazine compounds (1) to (8), 10 parts of chlorothalonil, 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
5 parts of any of the present pyridazine compounds (1) to (8), 10 parts of benomyl, 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 37
5 parts of any of the present pyridazine compounds (1) to (8), 10 parts of dicrosimet, 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 (8), 10 parts of furametopir, 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 pyridazine compounds (1) to (8), 10 parts of ferrimzone, 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
5 parts of any of the present pyridazine compounds (1) to (8), 10 parts of validamycin, 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 41
5 parts of any of the present pyridazine compounds (1) to (8), 10 parts of dietofencarb, 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 42
5 parts of any one of the present pyridazine compounds (1) to (8), 10 parts of tolcrophosmethyl, 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 43
5 parts of any of the present pyridazine compounds (1) to (8), 10 parts of 4-oxo-4-[(2-phenylethyl) amino] -butyric acid, 1.5 parts of sorbitan trioleate and polyvinyl alcohol -After mixing 28.5 parts of an aqueous solution containing 2 parts of the slurry and pulverizing it by a wet grinding method, 45 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate was added thereto. Further, 10 parts of propylene glycol is added and mixed with stirring to obtain each preparation.

Formulation Example 44
5 parts of any of the present pyridazine compounds (1) to (8), 10 parts of N-methyl-α-methoxyimino-2-[(2,5-dimethylphenoxy) methyl] phenylacetamide, sorbitan trioleate After mixing 28.5 parts of an aqueous solution containing 1.5 parts and 2 parts of polyvinyl alcohol, and finely pulverizing by a wet pulverization method, 0.05 parts of xanthan gum and 0.1 parts of aluminum magnesium silicate were added thereto. An aqueous solution containing 45 parts is added, and further 10 parts of propylene glycol is added and mixed by stirring to obtain each preparation.

Formulation Example 45
5 parts of any one of the pyridazine compounds (1) to (8), 10 parts of procymidone, 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 46
5 parts of any one of the present pyridazine compounds (1) to (8), 10 parts of thiodicarb, 28.5 parts of an aqueous solution containing 1.5 parts of sorbitan trioleate and 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 47
5 parts of any of the present pyridazine compounds (1) to (8), 10 parts of carbofuran, 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 48
5 parts of any of the present pyridazine compounds (1) to (8), 10 parts of fludioxonil, 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 49
1 part of any of the pyridazine compounds (1) to (8), 4 parts of sulfoxafur, 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 50
1 part of any of the present pyridazine compounds (1) to (8), 4 parts of mancozeb, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 62 parts of kaolin clay are thoroughly mixed. After adding water and kneading well, each formulation is obtained by granulating and drying.

Formulation Example 51
1 part of any of the present pyridazine compounds (1) to (8), 4 parts of chlorothalonil, 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 52
1 part of any of the present pyridazine compounds (1) to (8), 4 parts of benomyl, 1 part of synthetic silicon hydroxide, 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 (8), 4 parts of dicrosimet, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 62 parts of kaolin clay are mixed well. After adding water and kneading well, each formulation is obtained by granulating and drying.

Formulation Example 54
1 part of any one of the present pyridazine compounds (1) to (8), 4 parts of furametopil, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 62 parts of kaolin clay are thoroughly mixed. After adding water and kneading well, each formulation is obtained by granulating and drying.

Formulation Example 55
1 part of any of the present pyridazine compounds (1) to (8), 4 parts of ferrimzone, 1 part of synthetic silicon hydroxide, 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 56
1 part of any of the present pyridazine compounds (1) to (8), 4 parts of validamycin, 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 57
1 part of any of the present pyridazine compounds (1) to (8), 4 parts of dietofencarb, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 62 parts of kaolin clay are mixed well. After adding water and kneading well, each formulation is obtained by granulating and drying.

Formulation Example 58
1 part of any one of the present pyridazine compounds (1) to (8), 4 parts of tolcrofosmethyl, 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 59
1 part of any of the present pyridazine compounds (1) to (8), 4 parts of 4-oxo-4-[(2-phenylethyl) amino] -butyric acid, 1 part of synthetic hydrous silicon oxide, calcium lignin sulfonate 2 Parts, 30 parts of bentonite and 62 parts of kaolin clay are added to each other by pulverization and mixing.

Formulation Example 60
1 part of any one of the present pyridazine compounds (1) to (8), 4 parts of N-methyl-α-methoxyimino-2-[(2,5-dimethylphenoxy) methyl] phenylacetamide, synthetic silicon hydroxide 1 Parts, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 62 parts of kaolin clay are added to each other by pulverization and mixing.

Formulation Example 61
1 part of any of the present pyridazine compounds (1) to (8), 4 parts of procymidone, 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 62
1 part of any of the present pyridazine compounds (1) to (8), 4 parts of thiodicarb, 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 63
1 part of any of the present pyridazine compounds (1) to (8), 4 parts of carbofuran, 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 64
1 part of any one of the present pyridazine compounds (1) to (8), 4 parts of fludioxonil, 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 65
1 part of any of the pyridazine compounds (1) to (8), 4 parts of sulfoxafur, 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 66
1 part of any of the present pyridazine compounds (1) to (8), 4 parts of mancozeb, 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 67
12.5 parts of any one of the pyridazine compounds (1) to (8), 37.5 parts of dicrosimet, 3 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and 45 parts of synthetic hydrous hydroxide are thoroughly pulverized and mixed. Each formulation is obtained.

Formulation Example 68
3 parts of any of the present pyridazine compounds (1) to (8), 2 parts of mancozeb, 85 parts of kaolin clay and 10 parts of talc are thoroughly pulverized and mixed to obtain a preparation.

Next, the effect of the present invention will be shown by test examples.

Test example 1
A test compound having a predetermined weight per 10 g of wheat (cultivar: 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 disease incidence is determined by the following formula (1).
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 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 (3)

Formula (I)

[Where,
R ¹ represents a chlorine atom, a bromine atom, a cyano group or a methyl group,
R ² represents a hydrogen atom or a fluorine atom. ]
The plant disease control composition containing the pyridazine compound shown by these, and 1 or more types of compounds chosen from the group A-group F.
Group A; fungicide group B; insecticide group C; acaricide group D; nematicide group E; safener group F; plant growth regulator Formula (I)

[Where,
R ¹ represents a chlorine atom, a bromine atom, a cyano group or a methyl group,
R ² represents a hydrogen atom or a fluorine atom. ]
The plant disease control method including the process of processing the effective amount of the pyridazine compound shown by these, and 1 or more types of compounds chosen from the group A-the group F to the soil which grows a plant or a plant.
Group A; fungicide group B; insecticide group C; acaricide group D; nematicide group E; safener group F; plant growth regulator   The plant disease control method according to claim 2, wherein the plant or the soil in which the plant is cultivated is wheat or soil in which the wheat is cultivated.