JP6922271B2 - Plant disease control composition and plant disease control method - Google Patents

Description

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

Conventionally, many compounds are known as active ingredients of plant disease control compositions (see, for example, Patent Documents 1, 2 and 3).

International Publication No. 2012/020772 International Publication No. 2011/017547 International Publication No. 2014/105845

An object of the present invention is to provide a composition having an excellent control effect on plant diseases and a method for controlling plant diseases.

〔式中、
Ｘは、フッ素原子または水素原子を表す。〕
で示されるピリダジン化合物と、
下記群（Ａ）より選ばれる1種以上の５−フルオロウラシル化合物とを含有する植物病害防除組成物。
群（Ａ）：４−アミノ−５−フルオロ−１−トシルピリミジン−２（１Ｈ）−オン、５−フルオロ−４−イミノ−３−メチル−１−トシル−３，４−ジヒドロピリミジン−２（１Ｈ）−オン及び５−フルオロ−３−メチル−４−（メチルイミノ）−１−トシル−３，４−ジヒドロピリミジン−２（１Ｈ）−オンからなる群。
［２］ピリダジン化合物が、
式（１）において、
Ｘが水素原子である
［１］に記載の植物病害防除組成物。
［３］ ピリダジン化合物と５−フルオロウラシル化合物との重量比が、１：０．０１２５〜１：５００の範囲である［１］または［２］に記載の植物病害防除組成物。
［４］ 下記式（１）

〔式中、
Ｘは、フッ素原子または水素原子を表す。〕
で示されるピリダジン化合物と、
下記群（Ａ）より選ばれる1種以上の５−フルオロウラシル化合物との有効量を植物また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）：４−アミノ−５−フルオロ−１−トシルピリミジン−２（１Ｈ）−オン、５−フルオロ−４−イミノ−３−メチル−１−トシル−３，４−ジヒドロピリミジン−２（１Ｈ）−オン及び５−フルオロ−３−メチル−４−（メチルイミノ）−１−トシル−３，４−ジヒドロピリミジン−２（１Ｈ）−オンからなる群。
［５］ 下記式（１）

〔式中、
Ｘは、フッ素原子または水素原子を表す。〕
で示されるピリダジン化合物と、
下記群（Ａ）より選ばれる1種以上の５−フルオロウラシル化合物との有効量を種子に処理する工程を含む植物病害防除方法。
群（Ａ）：４−アミノ−５−フルオロ−１−トシルピリミジン−２（１Ｈ）−オン、５−フルオロ−４−イミノ−３−メチル−１−トシル−３，４−ジヒドロピリミジン−２（１Ｈ）−オン及び５−フルオロ−３−メチル−４−（メチルイミノ）−１−トシル−３，４−ジヒドロピリミジン−２（１Ｈ）−オンからなる群。
［６］ 下記式（１）

〔式中、
Ｘは、フッ素原子または水素原子を表す。〕
で示されるピリダジン化合物と、
下記群（Ａ）より選ばれる1種以上の５−フルオロウラシル化合物との組合せの使用。
群（Ａ）：４−アミノ−５−フルオロ−１−トシルピリミジン−２（１Ｈ）−オン、５−フルオロ−４−イミノ−３−メチル−１−トシル−３，４−ジヒドロピリミジン−２（１Ｈ）−オン及び５−フルオロ−３−メチル−４−（メチルイミノ）−１−トシル−３，４−ジヒドロピリミジン−２（１Ｈ）−オンからなる群。 As a result of studies to find a composition having an excellent control effect on plant diseases and a method for controlling plant diseases, the present inventor has selected a pyridazine compound represented by the following formula (1) and one selected from the following group (A). It has been found that the composition containing the above 5-fluorouracil compound has an excellent control effect against plant diseases.
That is, the present invention is as follows.
[1] The following formula (1)

[In the formula,
X represents a fluorine atom or a hydrogen atom. ]
With the pyridazine compound indicated by
A plant disease control composition containing one or more 5-fluorouracil compounds selected from the following group (A).
Group (A): 4-amino-5-fluoro-1-tosylpyrimidine-2 (1H) -one, 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidine-2 ( A group consisting of 1H) -one and 5-fluoro-3-methyl-4- (methylimino) -1-tosyl-3,4-dihydropyrimidine-2 (1H) -one.
[2] The pyridazine compound is
In equation (1)
The plant disease control composition according to [1], wherein X is a hydrogen atom.
[3] The plant disease control composition according to [1] or [2], wherein the weight ratio of the pyridazine compound to the 5-fluorouracil compound is in the range of 1: 0.0125 to 1: 500.
[4] The following formula (1)

[In the formula,
X represents a fluorine atom or a hydrogen atom. ]
With the pyridazine compound indicated by
A plant disease control method comprising a step of treating a plant or the soil in which the plant is cultivated with an effective amount of one or more 5-fluorouracil compounds selected from the following group (A).
Group (A): 4-amino-5-fluoro-1-tosylpyrimidine-2 (1H) -one, 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidine-2 ( A group consisting of 1H) -one and 5-fluoro-3-methyl-4- (methylimino) -1-tosyl-3,4-dihydropyrimidine-2 (1H) -one.
[5] The following formula (1)

[In the formula,
X represents a fluorine atom or a hydrogen atom. ]
With the pyridazine compound indicated by
A plant disease control method comprising a step of treating seeds with an effective amount of one or more 5-fluorouracil compounds selected from the following group (A).
Group (A): 4-amino-5-fluoro-1-tosylpyrimidine-2 (1H) -one, 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidine-2 ( A group consisting of 1H) -one and 5-fluoro-3-methyl-4- (methylimino) -1-tosyl-3,4-dihydropyrimidine-2 (1H) -one.
[6] The following formula (1)

[In the formula,
X represents a fluorine atom or a hydrogen atom. ]
With the pyridazine compound indicated by
Use in combination with one or more 5-fluorouracil compounds selected from the following group (A).
Group (A): 4-amino-5-fluoro-1-tosylpyrimidine-2 (1H) -one, 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidine-2 ( A group consisting of 1H) -one and 5-fluoro-3-methyl-4- (methylimino) -1-tosyl-3,4-dihydropyrimidine-2 (1H) -one.

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

The plant disease control composition of the present invention (hereinafter referred to as the composition of the present invention) is selected from the pyridazine compound represented by the formula (1) (hereinafter referred to as the present compound 1) and the group (A). Contains one or more 5-fluorouracil compounds (hereinafter referred to as the present compound A).

First, the present compound 1 will be described.

The present compound 1 is, for example, the compound described in International Publication No. 2012/020772, and can be produced by the method described therein.

Examples of the present compound 1 include the compounds shown in Table 1.

Next, the present compound A will be described.

The present compound A is, for example, the compounds described in International Publication No. 2011/017547 and International Publication No. 2014/105845, and can be produced by the methods described therein.

Examples of the present compound A include the following compounds.
4-Amino-5-fluoro-1-tosylpyrimidine-2 (1H) -one (hereinafter referred to as this compound A-1).
5-Fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidine-2 (1H) -one (hereinafter referred to as this compound A-2).
5-Fluoro-3-methyl-4- (methylimino) -1-tosyl-3,4-dihydropyrimidine-2 (1H) -one (hereinafter referred to as this compound A-3).

The weight ratio of the present compound 1 to the present compound A in the composition of the present invention is usually 1: 0.0125 to 1: 500, preferably 1: 0.025 to 1: 100, and more preferably 1: 0.1. ~ 1:10.

The composition of the present invention may be a mixture of the present compound 1 and the present compound A itself, but the composition of the present invention is usually a mixture of the present compound 1, the present compound A and an inert carrier, and is surface-active as necessary. It is a preparation formulated into an oil, an emulsion, a flowable agent, a wettable powder, a granule wettable powder, a powder, a granule, or the like by adding an agent or other pharmaceutical auxiliary agent. Such a preparation can be used as it is or by adding other inert ingredients as a plant disease control agent.
The composition of the present invention contains the present compound 1 and the present compound A as a total of 0.1 to 99% by weight, preferably 0.2 to 90% by weight, and more preferably 1 to 80% by weight. ..

Examples of the inert carrier used in the formulation include a solid carrier and a liquid carrier, and examples of the solid carrier include kaolin clay, attapargite clay, bentonite, montmorillonite, acidic clay, pyrophyllite, talc, and diatomaceous earth. Fine powders or granules consisting of minerals such as montmorillonite, natural organic substances such as montmorillonite powder and walnut shell powder, synthetic organic substances such as urea, salts such as calcium carbonate and ammonium sulfate, and synthetic inorganic substances such as synthetic silicon hydroxide-containing silicon. Can be mentioned. Examples of the liquid carrier include aromatic hydrocarbons such as xylene, alkylbenzene and methylnaphthalene, alcohols such as 2-propanol, ethylene glycol, propylene glycol and ethylene glycol monoethyl ether, and ketones such as acetone, cyclohexanone and isophorone. Examples include vegetable oils such as soybean oil and cottonseed oil, petroleum-based aliphatic hydrocarbons, esters, dimethylsulfoxide, acetonitrile and water.
Examples of the surfactant include anionic surfactants such as alkyl sulfates, alkylaryl sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkylaryl ether phosphates, lignin sulfonates, and naphthalene sulfonate formaldehyde polycondensates. Examples thereof include activators and nonionic surfactants such as polyoxyethylene alkylaryl ethers, polyoxyethylene alkyl polyoxypropylene block copolymers and sorbitan fatty acid esters, and cationic surfactants such as alkyltrimethylammonium salts.
Other pharmaceutical auxiliary agents include, for example, water-soluble polymers such as polyvinyl alcohol and polyvinylpyrrolidone, arabic gum, alginic acid and salts thereof, polysaccharides such as CMC (carboxymethyl cellulose) and zansan gum, aluminum magnesium silicate, and alumina sol. Examples thereof include inorganic substances such as, preservatives, colorants and stabilizers such as PAP (acidic isopropyl phosphate) and BHT (2,6-di-tert-butyl-4-methylphenol).

The composition of the present invention is also prepared by formulating the present compound 1 and the present compound A by the above-mentioned methods, diluting them with water as necessary, and mixing the respective preparations or their diluted solutions. You can also do it.

The composition of the present invention may further contain one or more other fungicides and / or insecticides.

Plant diseases can be controlled by treating the composition of the present invention with a plant or the soil in which the plant is cultivated.

Examples of plant diseases that can be controlled by the present invention include, but are not limited to, the following diseases.

Rice diseases: Magnaporthe grisea, Cochliobolus miyabeanus, Rhizoctonia solani, Gibberella fujikuroi.
Wheat diseases: Udonko disease (Erysipe graminis), Fusarium graminearum, F. avenceum, F. culmorum, Microdochium nivale, rust disease (eg, yellow rust (Pyrenophora trici) black rust (Pyrenophora trici) Graminis), Fusarium head blight (P. recondita)), Monographella nivalis (Microdochium nivale), Pyrenophora sp. Blight (Pseudocercosporella herpotorichoides), leaf blight (Mycosphaerella gramicola), blight (Stagonospora nodolum), yellow spot disease (Pyrenophora tritici-repentis).
Diseases of barley: Udonko disease (Erysipe graminis), Fusarium graminearum, F. avenaceum, F. culmorum, Microdochium nivale, Rhizoctonia (Puccinia) Rhizoctonia. Ustylago nuda), cloud-shaped disease (Rhinchosporium secalis), net spot disease (Pyrenophora teres), spot disease (Cochliobolus sativus), leaf disease (Pyrenophora graminea), Rhizoctonia seedlings.
Corn diseases: corn smut (Ustilago maydis), sesame leaf blight (Cochliobolus heterostrophos), gourd scab (Gloocercospora sorghi), southern rust (Puccinia polysora), Rhizoctonia serrata, gray leaf spot Seedling blight (Rhizoctonia solani).

Diseases of citrus fruits: Black spot disease (Diaporthe citri), scab (Elsinoe phytophthora), fruit rot disease (Penicillium digitatum, P. italicum), Phytophthora psychiatrica.
Apple diseases: Monilinia mari, Valsa ceratosperma, Powdery mildew, Alternaria alternata, Apple scab, Alternaria alternata, Apple scab, Alternaria alternata, Apple scab, Alternaria alternata, Apple scab, Alternaria alternata , Plague (Phytophthora cattorum).
Pear disease: Black spot disease (Venturia nashicola, V. pilina), Black spot disease (Alternaria alternata Japane sea pear pattern), Gymnosporangium disease
Diseases of peaches: Monilinia fructicola, Cladosporium carpophilum, Phomopsis sp.
Diseases of grapes: black rot (Elsinoe ampelina), late rot (Glomerella cingulata), powdery mildew (Uncinula necator), rust (Phakopora ampelopsis), black rot disease (Guigarbia) ..
Diseases of persimmon: Anthrax (Gloeosporium kaki), Deciduous disease (Cercospora kaki, Mycosphaerella nawae).
Diseases of uris: Colletotrichum lagenarium, powdery mildew (Sphaerotheca fuliginea), vine blight (Mycosphaerella melonis), vine split disease (Fusarium oxysporum), downy mildew (Fusarium oxysporum), downy mildew (Fusarium oxysporum) ), Seedling blight (Pythium sp.);
Diseases of tomatoes: Alternaria solani, Cladosporium fullvum, Phytophthora influences.
Diseases of eggplant: Phomopsis vexans, powdery mildew (Erysiphe cichoracealum).
Diseases of cruciferous vegetables: Black spot disease (Alternaria japonica), white spot disease (Cercosporella brassicae), root-knot disease (Plasmodiophora brassicae), downy mildew (Peronospora parasita).
Welsh onion diseases: rust (Puccinia alli), downy mildew (Peronospora destructor).

Diseases of soybeans: purple spot disease (Cercospora kikuchii), black scab (Elsinoe glycines), black spot disease (Diaporthe phaseolorum var. , Phytophthora sojae, Rhizoctonia soybean, Rhizoctonia soly, Corynespora casicicola, Sclerotia sclerotiorum.
Common bean disease: Colletotrichum anthrax.
Diseases of peanuts: black astringent disease (Cercospora personata), brown spot disease (Cercospora arachidicola), white silk disease (Sclerotium lorfsii).
Pea disease: powdery mildew (Erysiphe pisi).
Potato diseases: Alternaria solani, Phytophthora underground, Phytophthora erythroseptica, Spongospora subterranean.
Strawberry diseases: powdery mildew (Sphaerotheca humuli), anthrax (Glomerella cingulata).
Diseases of tea: Exobasidium reticularatum, Elsinoe leucopilia, Pestalotiopsis sp., Colletotrichum theae-sinensis.
Tobacco diseases: Gymnosporangium (Alternaria longipes), powdery mildew (Erysiphe cichoracealum), anthrax (Collettrichum tabacum), downy mildew (Peronospora tabacina), epidemic (Phytophthora).
Diseases of rapeseed: Sclerotinia sclerotiorum, Rhizoctonia solani caused by Rhizoctonia spp.
Cotton disease; Rhizoctonia solani caused by Rhizoctonia spp.
Diseases of sugar beet: Cercospora beticola, leaf rot (Thanatephorus cucumeris), root rot (Thanatephorus cucumeris), black root disease (Aphanomyces cochlioides).
Diseases of roses: Diplocarpon rosae, powdery mildew (Sphaerotheca pannosa), downy mildew (Peronospora spursa).
Diseases of chrysanthemum and Asteraceae vegetables: downy mildew (Bremia lactucae), septoria chrysanthemi-indici, white rust (Puccinia horiana).
Diseases of various crops: Diseases caused by the genus Pythium (Pythium aphanidermatum, Pythium debarianum, Pythium glaminicola, Pythium irregulare, Pythium cinerea, Botrytis cinerea, Botrytis cinerea, Botrytis cinerea, Botrytis cinerea, Botrytis cinerea.
Radish disease: Black spot disease (Alternaria brassicola).
Diseases of Shiva: Dollar spot disease (Sclerotinia homeocarpa), Brown patch disease and Large patch disease (Rhizoctonia solani).
Banana disease: Black sigatoka (Mycosphaerella fijiensis, Mycosphaerella mycosphaerella).
Sunflower disease: Downy mildew (Plasmopara halstedii).
Aspergillus, Pencillium, Fusarium, Gibbellala, Tricoderma, Thielaviopsis, Rhizopus, Mucor, Corticium, Phoma, Early crops of Rhizoctonia, etc. Diseases.
Viral diseases of various crops transmitted by the genus Polymixa or the genus Olpidium.

Examples of plants to which the composition of the present invention can be used include, but are not limited to, the following plants.

Agricultural crops: corn, rice, wheat, barley, lime, embaku, sorghum, cotton, soybean, adzuki bean, green bean, peanut, buckwheat, sugar beet, rapeseed, sunflower, sugar beet, tobacco, etc.
Vegetables; Labiatae vegetables (nass, tomatoes, peppers, capsicum, potatoes, etc.), Uriaceae vegetables (cucumbers, pumpkins, zucchini, watermelons, melons, squash, etc.) , Cabbage, Karasina, broccoli, cauliflower, etc.), Labiatae vegetables (gobo, shungiku, artichoke, lettuce, etc.), lily vegetables (green onions, onions, garlic, asparagus), Labiatae vegetables (carrots, parsley, celery, America) Bowfu etc.), Akaza family vegetables (Horensou, Fudansou etc.), Labiatae vegetables (Shiso, Mint, Basil etc.), Strawberries, Sweet potatoes, Yamanoimo, Satoimo etc.
Flower,
Foliage plant,
Shiva,
Fruit trees: Nuts (apples, pears, Japanese pears, curins, marmelos, etc.), drupes (peaches, peaches, nectarines, sea urchins, apricots, apricots, prunes, etc.), citrus fruits (unshu mikan, orange, lemon, lime, grapefruit, etc.) Etc.), nuts (chestnuts, walnuts, hashibami, almonds, pistachios, cashew nuts, macadamia nuts, etc.), berries (blueberries, cranberries, blackberries, raspberries, etc.), grapes, oysters, olives, biwa, bananas, coffee, Nut palm, coco palm, etc.
Trees other than fruit trees; cha, mulberry, flowering tree, roadside tree (ash, kabanoki, hanamizuki, eucalyptus, ginkgo, lilac, maple, oak, poplar, hanazuou, fu, sycamore, zelkova, kurobe, mominoki, tsuga, rat, pine, Tohi, Ichii) etc.

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

Examples of aspects of the composition of the present invention include the following.

The composition of the present invention in which the combination of the present compound 1 and the present compound A is the following combination:
Combination of this compound 1-1 and this compound A-1;
Combination of this compound 1-1 and this compound A-2;
Combination of this compound 1-1 and this compound A-3;
Combination of this compound 1-2 and this compound A-1;
Combination of this compound 1-2 and this compound A-2;
Combination of this compound 1-2 and this compound A-3;

A composition containing the present compound 1-1 and any one of the present compounds A-1 to A-3 in a weight ratio of 1: 0.0125 to 1: 500;
A composition containing the present compound 1-1 and any one of the present compounds A-1 to A-3 in a weight ratio of 1: 0.025 to 1: 100;
A composition containing the present compound 1-1 and any one of the present compounds A-1 to A-3 in a weight ratio of 1: 0.1 to 1:10;
A composition containing the present compound 1-2 and any one of the present compounds A-1 to A-3 in a weight ratio of 1: 0.0125 to 1: 500;
A composition containing the present compound 1-2 and any one of the present compounds A-1 to A-3 in a weight ratio of 1: 0.025 to 1: 100;
A composition containing the present compound 1-2 and any one of the present compounds A-1 to A-3 in a weight ratio of 1: 0.1 to 1:10;

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 compound 1 and the present compound A on a plant or soil in which the plant is cultivated. Such plants include, for example, plant foliage, plant seeds and plant bulbs. Here, the bulb means a bulb, a corm, a rhizome, a tuber, a tuber, and a root-bearing body.

In the control method of the present invention, the present compound 1 and the present compound A may be separately treated on a plant or soil in which a plant is cultivated at the same time, but usually, from the viewpoint of convenience at the time of treatment, as the composition of the present invention. It is processed.

In the control method of the present invention, examples of the method for treating the present compound 1 and the present compound A include foliage treatment, soil treatment, root treatment and seed treatment.

Examples of such foliage treatment include a method of treating the present compound 1 and the present compound A on the surface of a cultivated plant by foliar spraying and tree trunk spraying.
Examples of such soil treatment include soil spraying, soil mixing, and irrigation of the soil with a chemical solution containing the present compound 1 and the present compound A.
Examples of such root treatment include a method of immersing the whole plant or the root in a chemical solution containing the present compound 1 and the present compound A, and a solid preparation containing the present compound 1, the present compound A and a solid carrier. A method of attaching to the root of a plant can be mentioned.
Examples of such seed treatment include treatment of the seeds or bulbs of a plant to be protected from plant diseases, and more specifically, for example, a suspension of the composition of the present invention is atomized into seeds. Spray treatment on the surface or bulb surface, smear treatment to apply to seeds or bulbs with or without adding a small amount of water to the wettable powder, emulsion or flowable agent of the composition of the present invention, solution of the composition of the present invention. Examples include a dipping treatment in which seeds are immersed for a certain period of time, a film coating treatment, and a pellet coating treatment.

The treatment amount of the present compound 1 and the present compound A in the control method of the present invention includes the type of plant to be treated, the type and frequency of occurrence of plant diseases to be controlled, the formulation form, the treatment time, the treatment method, the treatment place, and the weather. Although it depends on the conditions, when treating the foliage of the plant or the soil where the plant is cultivated, the total amount of the present compound 1 and the present compound A is ^{usually 1 to 500 g per 1000 m 2} , preferably 1 to 500 g. It is 2 to 200 g, more preferably 10 to 100 g. The amount of the present compound 1 and the present compound A treated in the treatment of seeds is the total amount of the present compound 1 and the present compound A, which is usually 0.001 to 10 g, preferably 0.01 to 1 g, per 1 kg of seeds. Is.
Emulsions, wettable powders, flowable agents, etc. are usually treated by diluting with water and spraying. In this case, the concentration of the present compound 1 and the present compound A is the total concentration of the present compound 1 and the present compound A, which is usually 0.0005 to 2% by weight, preferably 0.005 to 1% by weight. Powders, granules, etc. are usually treated as they are without dilution.

Hereinafter, the present invention will be described in more detail with reference to pharmaceutical examples and test examples, but the present invention is not limited to these examples.

An example of the formulation is shown. In the formulation example, the part represents a part by weight.

Pharmaceutical example 1
1-1 5 parts of this compound, 5 parts of any one of this compound A-1 to A-3, 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) And 55 parts of water are mixed and finely pulverized by a wet pulverization method to obtain a flowable preparation.

Pharmaceutical example 2
1-2 5 parts of this compound, 5 parts of any one of this compound A-1 to this compound A-3, 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) And 55 parts of water are mixed and finely pulverized by a wet pulverization method to obtain a flowable preparation.

Pharmaceutical example 3
Wet by mixing 10 parts of this compound 1-1 10 parts, 5 parts of any one compound of this compound A-1 to this compound A-3, 1.5 parts of sorbitan trioleate, and 28 parts of an aqueous solution containing 2 parts of polyvinyl alcohol. After finely pulverizing by the pulverization method, 45.50 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added thereto, and 10 parts of propylene glycol is further added and mixed by stirring to obtain a flowable preparation. ..

Pharmaceutical example 4
Wet by mixing 10 parts of this compound 1-2 10 parts, 5 parts of any one compound of this compound A-1 to this compound A-3, 1.5 parts of sorbitan trioleate, and 28 parts of an aqueous solution containing 2 parts of polyvinyl alcohol. After finely pulverizing by the pulverization method, 45.50 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added thereto, and 10 parts of propylene glycol is further added and mixed by stirring to obtain a flowable preparation. ..

Pharmaceutical example 5
10 parts of this compound 1-1 10 parts, 40 parts of any one compound of this compound A-1 to this compound A-3, 3 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate and 45 parts of synthetic silicon hydroxide-containing silicon are thoroughly pulverized and mixed. By doing so, a wettable powder is obtained.

Pharmaceutical example 6
10 parts of this compound 1-2 10 parts, 40 parts of any one compound of this compound A-1 to this compound A-3, 3 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate and 45 parts of synthetic silicon hydroxide-containing silicon are thoroughly pulverized and mixed. By doing so, a wettable powder is obtained.

Pharmaceutical example 7
1-1 5 parts of this compound, 5 parts of any one of this compound A-1 to A-3, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 70 parts of xylene. Mix well to obtain the formulation.

Pharmaceutical example 8
1-25 parts of this compound, 5 parts of any one of this compound A-1 to A-3, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 70 parts of xylene. Mix well to obtain the formulation.

Next, a test example is shown.

Test Example 1
The present compound 1-1 or the present compound 1-2 is mixed with any one of the present compounds A-1 to the present compound A-3, and each of the mixtures is dimethyl sulfoxide, respectively, of the present compound 1 and the present compound A. Dilute to a concentration of 10 ppm. After dispensing 1 μl of the obtained diluted solution into each well of the titer plate (96 wells), 150 μl of potato decoction liquid medium (PDB medium) inoculated with conidia of Zymoseptoria trichophylla in advance. Note. This plate is cultured at 18 ° C. for 4 days to grow the wheat leaf blight, and then the growth of the wheat leaf blight is measured by the absorbance at 550 nm in each well of the titer plate. Based on the growth rate of each of the treated and untreated plots, the efficacy is calculated using the following "Equation 1". As a result, it is recognized that it shows high efficacy.
"Equation 1"
Efficacy = 100 × (XY) / X
X: Growth rate of bacteria in the untreated group Y: Growth rate of bacteria in the treated group

Test Example 2
A chemical solution prepared by dissolving the present compound 1-1 and the present compound A-2 in dimethyl sulfoxide and adjusting the concentration of each compound to be 150 times the concentration shown in Table 2 was prepared on a microtiter plate (96). 1 μl was dispensed into each well of the well). A well in which 149 μl of YBG medium (10 g of yeast extract, 10 g of bactobeptone, and 20 ml of glycerol dissolved and sterilized in 1 L of water) inoculated with conidia of Zymoseptoria trichophylla in advance was dispensed with a drug solution. Dispensed to. After culturing this plate at 18 ° C. for 4 days to grow wheat leaf blight, the growth of wheat leaf blight was measured by the absorbance at 550 nm in each well of the titer plate (this is referred to as a treatment group). bottom). On the other hand, the chemical solution was replaced with dimethyl sulfoxide to grow wheat leaf blight fungi in the same manner as in the treated group, and the degree of growth was investigated (this was designated as the untreated group). The efficacy was calculated using the following "Equation 1" based on the growth rate of each of the treated group and the untreated group.
As a result, it was confirmed that the mixed use group of the present compound 1-1 and the present compound A-2 showed a synergistic effect as compared with each single use group.
"Equation 1"
Efficacy (%) = 100 × (XY) / X
X: Growth of bacteria in the untreated group Y: Growth of bacteria in the treated group

Claims (5)

The following formula (1)

[In the formula,
X represents a water atom. ]
With the pyridazine compound indicated by
A plant disease control composition containing 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidine-2 (1H) -one . The weight ratio of the pyridazine compound to 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidine-2 (1H) -one is in the range of 1: 0.0125 to 1: 500. The plant disease control composition according to claim 1. The following formula (1)

[In the formula,
X represents a water atom. ]
With the pyridazine compound indicated by
Plant disease control including the step of treating a plant or the soil in which the plant is cultivated with an effective amount of 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidine-2 (1H) -one. Method . The following formula (1)

[In the formula,
X represents a water atom]
With the pyridazine compound indicated by
A plant disease control method comprising a step of treating seeds with an effective amount of 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidine-2 (1H) -one . The following formula (1)

[In the formula,
X represents a water atom. ]
With the pyridazine compound indicated by
Use in combination with 5-fluoro-4-imino-3-methyl-1-tosyl-3,4-dihydropyrimidine-2 (1H) -one .