JPWO2018203560A1 - Eradication type multidrug-resistant plant disease control method - Google Patents

Abstract

The present invention provides an excretion type comprising a step of treating an effective amount of a pyridazine compound represented by the following formula (1) on a plant or a soil for cultivating the plant, the excretion type having excellent efficacy against an excretion type multidrug-resistant plant disease. Provided is a method for controlling a multidrug-resistant plant disease.

Description

This patent application claims the priority and benefit under the Paris Convention based on Japanese Patent Application No. 2017-091192 (filed on May 1, 2017), which is incorporated herein by reference. The entire contents of the disclosure are incorporated herein.
The present invention relates to a method for controlling an efflux type multidrug-resistant plant disease.

In recent years, bacteria that have acquired resistance to a plurality of plant disease control agents that have been used so far have emerged due to heavy use of plant disease control agents. It is said that these resistance-acquiring bacteria have acquired resistance to a plurality of plant disease controlling agents by mutation of the action point (target protein) of the plant disease controlling agent or acquisition of the resolution of the plant disease controlling agent. .
On the other hand, recently, by acquiring the ability to excrete plant disease control agents out of cells, the existence of bacteria that have acquired resistance to not only the plant disease control agents used so far but also other plant disease control agents Has been newly reported (for example, see Non-Patent Documents 1 and 2).

Pest Management Science. 2006; 62, 195-207. European Journal of Plant Pathology. 2013; 135, 683-693

  The present invention relates to a plant disease caused by a bacterium that has acquired resistance to a plant disease controlling agent by acquiring the ability to excrete a plant disease controlling agent out of cells (hereinafter sometimes referred to as an efflux type multidrug-resistant bacterium) , Which is sometimes referred to as an excretion-type multidrug-resistant plant disease).

で示されるピリダジン化合物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、排出型多剤耐性菌による植物病害の防除方法。
[２] 排出型多剤耐性菌が、ＡＢＣトランスポーターおよびＭＦＳトランスポーターからなる群から選ばれる少なくとも１つの膜輸送体の過剰発現により植物病害防除剤に対する耐性を獲得した菌である、[１]に記載の植物病害の防除方法。
[３] 植物病害が、コムギの病害およびブドウの病害からなる群から選ばれる少なくとも１つの植物病害である、[１]または[２]に記載の植物病害の防除方法。
[４] 排出型多剤耐性菌が、コムギ葉枯病菌およびブドウ灰色かび病菌からなる群から選ばれる少なくとも１つの排出型多剤耐性菌である、[１]または[２]に記載の植物病害の防除方法。
[５] 排出型多剤耐性菌が、呼吸阻害剤およびステロール生合成阻害剤からなる群から選ばれる少なくとも１つの植物病害防除剤に対して、当該植物病害防除剤の標的タンパク質をコードする遺伝子の変異に由来する耐性および／または当該標的タンパク質の過剰発現に由来する耐性を有する排出型多剤耐性菌である、[１]〜[４]のいずれか１項に記載の植物病害の防除方法。
[６] 植物または植物を栽培する土壌に処理する工程が、種子に処理する工程である、[１]〜[５]のいずれか１項に記載の植物病害の防除方法。
[７] 排出型多剤耐性菌による植物病害の防除のための、下記式（１）：

で示されるピリダジン化合物の使用。The present inventors have studied to find a method having an excellent controlling effect on efflux-type multidrug-resistant plant diseases, and as a result, have found that the pyridazine compound represented by the following formula (1) is effective against efflux-type multidrug-resistant plant diseases. It has been found that it has an excellent controlling effect.
That is, the present invention is as follows.
[1] The following formula (1):

A method for controlling a plant disease caused by an excretion-type multidrug-resistant bacterium, comprising a step of treating a plant or a soil for cultivating the plant with an effective amount of a pyridazine compound represented by the formula:
[2] The efflux-type multidrug-resistant bacterium is a bacterium that has acquired resistance to a plant disease controlling agent by overexpression of at least one membrane transporter selected from the group consisting of an ABC transporter and an MFS transporter. [1] 3. The method for controlling plant diseases according to 1.).
[3] The method for controlling plant diseases according to [1] or [2], wherein the plant diseases are at least one plant disease selected from the group consisting of wheat diseases and grape diseases.
[4] The plant disease according to [1] or [2], wherein the efflux type multidrug-resistant bacterium is at least one efflux type multidrug-resistant bacterium selected from the group consisting of wheat leaf blight fungus and grape gray mold. How to control.
[5] The efflux-type multidrug-resistant bacterium is characterized in that, for at least one plant disease controlling agent selected from the group consisting of a respiratory inhibitor and a sterol biosynthesis inhibitor, a gene encoding a target protein of the plant disease controlling agent The method for controlling plant diseases according to any one of [1] to [4], which is an efflux-type multidrug-resistant bacterium having resistance derived from mutation and / or resistance derived from overexpression of the target protein.
[6] The method for controlling plant diseases according to any one of [1] to [5], wherein the step of treating the plant or the soil where the plant is grown is a step of treating the seed.
[7] The following formula (1) for controlling plant diseases caused by efflux type multidrug-resistant bacteria:

Use of a pyridazine compound represented by

  ADVANTAGE OF THE INVENTION According to this invention, the efflux type multi-drug resistant plant disease can be controlled.

  The method for controlling an efflux-type multidrug-resistant plant disease of the present invention (hereinafter, referred to as the method of the present invention) comprises an effective amount of a pyridazine compound represented by the above formula (1) (hereinafter, referred to as the present compound (1)). Treating the plant or soil where the plant is grown.

  First, the compound (1) will be described.

によって示されるピリダジン化合物であり、また、例えば、国際公開第２００５／１２１１０４号に記載されており、これに記載の方法により製造することもできる。This compound (1) has the following formula (1):

Which is described in, for example, WO 2005/121104, and can also be produced by the method described therein.

  As a form in which the present compound (1) is used, the present compound (1) may be used alone. However, usually, the present compound (1) is mixed with an inert carrier, and if necessary, a surfactant or another compound may be used. Formulation of wettable powder, wettable powder, flowable, granule, powder, dry flowable, emulsion, aqueous liquid, oil, smoke, aerosol, microcapsule, etc. (Hereinafter, referred to as the present formulation). For example, in these preparations, the present compound (1) contains usually 0.1 to 99% by weight, preferably 0.2 to 90% by weight, more preferably 5 to 50% by weight based on the total weight of the preparation. %. Such a preparation can be used as it is or with the addition of other inactive components, as an efflux-type multidrug-resistant plant disease controlling agent.

Inert carriers used in the formulation include solid carriers and liquid carriers.
As the solid carrier, for example, clays (for example, kaolin, diatomaceous earth, synthetic hydrated silicon oxide, fubasami clay, bentonite, acid clay), talc, and other inorganic minerals (for example, sericite, quartz powder, sulfur powder, activated carbon, Fine powder or granular material such as calcium carbonate and hydrated silica).
Examples of the liquid carrier include water, alcohols, ketones (eg, acetone, methyl ethyl ketone, cyclohexanone), aromatic hydrocarbons (eg, benzene, toluene, xylene, ethylbenzene, methylnaphthalene), and aliphatic hydrocarbons (eg, Examples thereof include n-hexane, kerosene), esters, nitriles, ethers, acid amides, and halogenated hydrocarbons.

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

  Examples of other pharmaceutical auxiliaries include, for example, fixing agents, dispersing agents, and stabilizers. Specifically, casein, gelatin, polysaccharides (eg, starch, gum arabic, cellulose derivatives, alginic acid), lignin derivatives, bentonite, Saccharides, synthetic water-soluble polymers (for example, polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids), PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (2 -Tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), fatty acids or esters thereof.

  In addition, the present preparation may be used by mixing with various oils such as mineral oil and vegetable oil, and / or other surfactants. Examples of oils and surfactants that can be specifically mixed and used include Nimbus (registered trademark), Assist (registered trademark), Aureo (registered trademark), Iharol (registered trademark), and Silwet L-77 (registered trademark). Trademark), BreakThru (registered trademark), Sundance II (registered trademark), Induce (registered trademark), Penetrator (registered trademark), AgriDex (registered trademark), Lutensol A8 (registered trademark), NP-7 (registered trademark), Triton (registered trademark) Registered trademark), Nufilm (registered trademark), Emulgator NP7 (registered trademark), Emulad (registered trademark), TRITON X45 (registered trademark), AGRAL 90 (registered trademark), AGROTIN (registered trademark), ARPON (registered trademark), EnSpray N Registered trademark), BANOLE (registered trademark), and the like.

  In the method of the present invention, the compound (1) may be used in combination with one or more compounds selected from other plant disease controlling active compounds, insecticidal active compounds and the like.

The method of the present invention is carried out by applying an effective amount of the present compound (1) to a plant or a soil where the plant is grown. 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 rhizome.
The application method of the present compound (1) is not particularly limited as long as the present compound (1) can be applied substantially, but for example, treatment of plants such as foliage application, cultivation of plants such as soil treatment and the like. Treatment of the ground, treatment of the seed such as seed disinfection, and the like are included.

Examples of such foliage treatment include a method of treating the surface of a cultivated plant by foliage application and stem application.
As the root treatment, for example, a method of immersing the whole or root of a plant in a drug solution containing the present compound (1), and a method of attaching a solid preparation containing the present compound (1) and a solid carrier to the root of a plant There is a method to make it.
Such soil treatments include, for example, soil application, soil admixture, and chemical solution irrigation into the soil.
Examples of such seed treatment include treatment of the seed or bulb of a plant to be protected from a plant disease with the present compound (1). Specifically, for example, a preparation containing the present compound (1) is mixed with water. A spraying process in which the mixture is atomized and sprayed on the surface of a seed or a bulb, and a small amount of water is added to a wettable powder, an emulsion or a flowable containing the compound (1), or applied to a seed or a bulb as it is. Coating treatment, dipping treatment of seeds in a solution of the present compound (1) for a certain period of time, film coating treatment and pellet coating treatment.

The amount of the present compound (1) to be treated in the method of the present invention also depends on the type of plant to be treated, the type and frequency of the plant disease to be controlled, the formulation, the treatment time, the treatment method, the treatment place, the weather conditions, and the like. The compound (1) is usually 1 to 500 g, preferably 5 to 50 g per 1000 m ² , when it is applied to the foliage of a plant or to the soil where the plant is grown, though different.
Emulsions, wettable powders, flowables and the like are usually processed by diluting with water and spraying. In this case, the concentration of the compound (1) is usually 0.0005 to 2% by weight, preferably 0.001 to 1% by weight. Dusts, granules and the like are usually treated without dilution.

In the present specification, the efflux-type multidrug-resistant bacterium is an overexpression of various membrane transporters present on the cell membrane, and the efflux pump function for excreting the plant disease control agent flowing into the cell to the outside of the cell is enhanced. Means a fungus that exhibits resistance to many plant disease control agents. Such membrane transporters include, but are not limited to, ABC transporters and MFS transporters. As used herein, the ABC transporter refers to an ATP-binding cassette transporters, and the MFS transporter refers to a major facilitator superfamily transporter. The overexpression of the membrane transporter is confirmed by a conventional method, for example, by measuring the amount of the membrane transporter or the amount of mRNA corresponding to the gene encoding the membrane transporter. The amount of the mRNA is measured by, for example, a quantitative reverse transcription polymerase chain reaction (qRT-PCR). More specifically, the following known literature discloses the measurement method.
Environmental Microbiology. 2015; 17 (8), 2805-2823.
Pest Management Science. 2001; 57 (5): 393-402.
PLoS Pathogen. 2009; Dec; 5 (12): e100696.
The efflux-type multidrug-resistant bacterium only needs to show resistance to the plant disease control agent as a result of overexpression of the membrane transporter regardless of the measured amount of mRNA. The measured amount of mRNA may be, for example, 20 times, 50 times, or even 100 times or more the amount of mRNA of a wild-type bacterium. Alternatively, as described later herein, EC ₅₀ values for emptying multidrug resistant strains, by dividing an EC ₅₀ value determined an EC ₅₀ value ratio against the wild-type strain, emptying multidrug resistant bacteria the indicator Is used to show that the EC ₅₀ value ratio of tolnaftate is at least 3 times, preferably at least 10 times higher.
The method of the present invention is applied to control plant diseases caused by excretion-type multidrug-resistant bacteria. As described above, the method of the present invention is carried out by applying an effective amount of the present compound (1) to a plant or a soil where the plant is grown. The plant is a plant in which a plant disease caused by the efflux type multidrug-resistant bacterium is occurring, or a plant in which a plant disease caused by the efflux type multidrug-resistant bacterium is likely to occur.

The efflux-type multidrug-resistant bacterium may have resistance derived from mutation of a gene encoding a target protein of various plant disease control agents and / or resistance derived from overexpression of the target protein. The target protein having a mutation in the gene or overexpressing the gene may be a plurality of types. However, the compound (1) does not have resistance to the compound (1) due to a mutation in the gene encoding the target protein.
Examples of the various plant disease controlling agents include nucleic acid synthesis inhibitors (eg, phenylamide-based fungicides, acylamino acid-based fungicides), mitotic and cell division inhibitors (eg, MBC fungicides, N-phenylcarbamate) Fungicides, respiratory inhibitors (eg, QoI fungicides, QiI fungicides, SDHI fungicides), inhibitors of amino acid synthesis and protein synthesis (eg, anilinopyrimidine fungicides), signal transduction inhibitors (eg, phenyl) Pyrrole fungicide, dicarboximide fungicide), inhibitor of lipid synthesis and cell membrane synthesis (for example, phosphorothiolate fungicide, dithiolane fungicide, aromatic hydrocarbon fungicide, heteroaromatic fungicide, carbamate) Fungicides), sterol biosynthesis inhibitors (eg, DMI fungicides such as triazoles, hydroxyanilides) Fungicides, aminopyrazolinone fungicides), cell wall synthesis inhibitors (eg, polyoxin fungicides, carboxylic amide fungicides), melanin synthesis inhibitors (eg, MBI-R fungicides, MBI-D fungicides) , MBI-P fungicides) and other fungicides (e.g., cyanoacetamide oxime fungicides, phenylacetamide fungicides), and are preferably selected from the group consisting of respiratory inhibitors and sterol biosynthesis inhibitors. It is at least one plant disease controlling agent. Examples of the mutation point of the gene encoding each target protein in each plant pathogen include those shown in Table 1 below.

The efflux type multidrug-resistant bacterium exhibits efflux type multidrug resistance, and is at least selected from the group consisting of the following (A), (B), (C-1), (C-2) and (C-3). It may be a wheat leaf blight fungus having one gene mutation point.
(A) Genes encoding cytochrome b: F129L, G137R, G143A;
(B) Gene encoding Cyp51: L50S, D107V, D134G, V136A / C / G, Y137F, M145L, N178S, S188N, S208T, N284H, H303Y, A311G, G312A, A379G, I381V / Δ, A410T, G410A, G412AY / D / N / S / P / Δ, G460D / Δ, Y461D / H / S, V490L, G510C, N513K, S524T;
(C-1) SDHB-encoding gene: N225I / T, H273Y, T268I / A, I269V;
(C-2) Genes encoding SDHC: I29V, N33T, N34T, T79I / N, W80S, A84V, N86K / S / A, G90R, R151T / S, H152R, I161S;
(C-3) Gene encoding SDHD: I50F, M114V, D129E.

The efflux type multidrug-resistant bacterium exhibits efflux type multidrug resistance and has at least one gene mutation selected from the group consisting of the following (D), (E-1), (E-2) and (E-3) It may be a grape gray fungus having a spot.
(D) a gene encoding cytochrome b: G143A;
(E-1) Gene encoding SDHB: P225H / F / L / T, N230I, H272L / R / V / Y;
(E-2) Gene encoding SDHC: P80H / L, A85V;
(E-3) Gene encoding SDHD: H132R.

  The present compound (1) can be used as an agent for controlling discharge-type multidrug-resistant plant diseases in agricultural lands such as fields, paddy fields, lawns, and orchards. The method of the present invention is applied to agricultural land or the like where the following “plants” are cultivated.

Agricultural crops: corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, buckwheat, sugar beet, rapeseed, sunflower, sugarcane, tobacco, etc.
Vegetables: Solanaceous vegetables (eggplant, tomato, pepper, capsicum, potato, etc.), Cucurbite vegetables (cucumber, pumpkin, zucchini, watermelon, melon etc.), Brassicaceae vegetables (daikon, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage , Mustard, broccoli, cauliflower, etc.), asteraceous vegetables (burdock, syngiku, artichoke, lettuce, etc.), lily family vegetables (leek, onion, garlic, asparagus), agaric vegetables (carrot, parsley, celery, american bob etc.) ), Akaza vegetables (spinach, chard etc.), Lamiaceae vegetables (perilla, mint, basil etc.), strawberry, sweet potato, yam, taro etc.
Flowers,
Foliage plant,
Shiva,
Fruit trees: Nuts (apples, pears, Japanese pears, karin, quince, etc.), drupes (peaches, plums, nectarines, plums, sweet cherry, apricots, prunes, etc.), citrus fruits (unshu mandarin orange, lemon, lime, grapefruit) ), Nuts (chestnut, walnut, hazelnut, 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, hanazou, fu, platanus, zelkova, kurobe, mominoki, tsuga, mouse, pine, Spruce, yew) and the like.

  The "plant" includes a genetically modified crop.

  Examples of the efflux-type multidrug-resistant plant disease that can be controlled by the present compound (1) include plant diseases caused by phytopathogenic fungi such as filamentous fungi. Specific examples include the following. However, the present invention is not limited to this.

Diseases of rice: blast (Magnaporthe grisea), sesame leaf blight (Cochliobolus miyabeanus), sheath blight (Rhizoctonia solani);
Wheat diseases: powdery mildew (Erysiphe graminis), rust (Puccinia striiformis, P. graminis, P. triticina), red snow rot (Micronectriella nivale, M. majus sclerotium, snow rot of M. majus) ), Eye spot disease (Pseudocercosporella herpotrichoides), leaf blight disease (Zymoseptoria tritici), blight disease (Stagonospora nodorum), yellow spot disease (Pyrenophora triticori zoni), and yellow spot disease (Pyrenophora tricholytica spores). Disease (Gaeumanomyces graminis);
Diseases of barley: powdery mildew (Erysiphe graminis), rust (Puccinia striiformis, P. graminis, P. hordei), scald disease (Rhynchosporium scalis), spot blotch (Pyrenophorativus spot) Leaf disease (Pyrenophora graminea), Lamularia disease (Ramularia collo-cygni), Seedling blight caused by Rhizoctonia sp. (Rhizoctonia solani);
Corn Diseases: Rust (Puccinia sorghi), Southern Rust (Puccinia polysora), Setophaeria turicica, Tropical Rust (Physopella zeoe, Leaf spot leaf blight) Cercospora zeae-maydis);
Cotton diseases: White mold (Ramuraria areola);
Diseases of coffee: rust (Hemileia vastatrix), leaf spot disease (Cercospora coffeicola);
Sugarcane diseases: rust (Puccinia melanocepela, Puccinia kuehnii);
Sunflower diseases: rust (Puccinia helianthi);
Disease of citrus: Black spot disease (Diaporthe citri), scab (Elsinoe fawcetti), fruit rot (Penicillium digitatum, P. italicum);
Diseases of apples: Monilinia mali, powdery mildew (Podosphaera leucotricha), scab (Venturia inaequalis), brown spot (Diplocarpon mali), ring spot disease (Botryaerya;
Diseases of pears: scab (Venturia nasicola, V. pirina), scab (Gymnosporangium haraeanum);
Peach diseases: Monilinia fructicola, scab (Cladosporium carpophilum), Phomopsis sp.
Grape diseases: Black scab (Elsinoe ampelina), powdery mildew (Uncinula necator), rust (Phakopsora ampelopsis), black lot disease (Guignardia bidwellii);
Oyster disease: deciduous disease (Cercospora kaki, Mycosphaerella nawae);
Diseases of cucurbits: powdery mildew (Sphaerotheca fuliginea), vine wilt (Didymella broniaiae), brown spot (Corynespora cassiicola);
Diseases of tomato: leaf mold (Cladosporium fulvum), scab (Pseudocercospora fuligena), powdery mildew (Leveillula taurica);
Diseases of eggplant: brown spot (Phomopsis vexans), powdery mildew (Erysiphe cichoracearum);
Leek diseases: rust (Puccinia allii);
Diseases of soybean: purpura (Cercospora kikuchii), rust (Phakopsora pachyrhizhi), brown ring spot (Corynespora cassiicola), leaf rot (Rhizotonia soligosa), spot blotch (Spotter) Powdery mildew (Microspaera diffusa);
Kidney diseases: Rust (Uromyces appendiculatus);
Peanut diseases: black rot (Cercospora personata), brown spot (Cercospora arachidicola);
Pea disease: powdery mildew (Erysiphe pisi);
Strawberry disease: powdery mildew (Sphaerotheca humuli);
Diseases of sugar beet: brown spot (Cercospora beticola), leaf rot (Thanatephorus cucumeris), root rot (Thanatephorus cucumeris);
Rose disease: powdery mildew (Sphaerotheca pannosa);
Chrysanthemum disease: Brown spot (Septoria chrysanthemi-indici);
Diseases of onion: Leaf spot blight (Botrytis cinerea, B. bysoidea, B. squamosa), gray rot (Botrytis alli), sclerotium rot (Botrytis squamosa);
Diseases of various crops: Botrytis cinerea;
Diseases of turf: Brown patch disease and large patch disease (Rhizoctonia solani);
Banana disease: Sigatoka disease (Mycosphaerella fijiensis, Mycosphaerella musicola).

  Hereinafter, the method of the present invention will be described in more detail with reference to formulation examples and test examples.

  The formulation examples used in the method of the present invention are shown. In the formulation examples, “parts” means “parts by weight”.

Formulation Example 1
A wettable powder is obtained by thoroughly pulverizing and mixing 50 parts of the present compound (1), 3 parts of calcium ligninsulfonate, 2 parts of magnesium lauryl sulfate and 45 parts of synthetic hydrous silicon oxide.

Formulation Example 2
20 parts of the present compound (1) and 1.5 parts of sorbitan trioleate are mixed with 28.5 parts of water containing 2 parts of polyvinyl alcohol, and finely pulverized by a wet pulverization method. And 40 parts of water containing 0.1 part of aluminum magnesium silicate, and 10 parts of propylene glycol are further added and stirred to obtain a flowable preparation.

Formulation Example 3
A powder is obtained by sufficiently pulverizing and mixing 2 parts of the present compound (1), 88 parts of kaolin clay and 10 parts of talc.

Formulation Example 4
An emulsion is obtained by thoroughly mixing 5 parts of the present compound (1), 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 75 parts of xylene.

Formulation Example 5
2 parts of the present compound (1), 1 part of synthetic hydrous silicon oxide, 2 parts of calcium ligninsulfonate, 30 parts of bentonite and 65 parts of kaolin clay are thoroughly pulverized and mixed, then water is added, kneaded well, and granulated and dried. Thus, a granule is obtained.

Formulation Example 6
20 parts of this compound (1); 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1: 1) and water are mixed to make a total amount of 100 parts, and treated using a pulverizer. As a result, a flowable preparation is obtained.

Formulation Example 7
The raw materials shown in Table 2 were mixed at the weight ratios shown in Table 2 and stirred until a uniform solution was obtained, to thereby obtain preparations. The numbers in the table indicate parts by weight.

The product names described in Table 2 above are as follows.
Agnique AMD810: a mixture of N, N-dimethyloctaneamide and N, N-dimethyldecaneamide, manufactured by BASF;
Hallcomid M-8-10: a mixture of N, N-dimethyloctaneamide and N, N-dimethyldecaneamide, manufactured by Stepan;
Agnique AMD3L: N, N-dimethyl lactamide, BASF;
Solvesso 200ND: mainly C11-14 alkylnaphthalene as an aromatic hydrocarbon, manufactured by ExxonMobil Chemical;
Calsogen 4814: calcium dodecylbenzenesulfonate, Clariant;
ATPLUS 245: polyoxyethylene polyoxypropylene alkyl ether, from Croda;
Brij O3: polyoxyethylene oleyl ether, HLB: 7, manufactured by Croda;
Atlas G5002L: butyl block copolymer, from Croda;
Toximul 8323: polyoxyethylene polyoxypropylene block copolymer, manufactured by Stepan;
Rhodiasolv Polarclean: 80-90% by weight of methyl 5- (dimethylamino) -2-methyl-5-oxopentanoate (the total amount is 100% by weight), manufactured by Solvay Nichika;
PURASOLV ML: L-methyl lactate, manufactured by Corbion purac;
PURASOLV EL: L-ethyl lactate, manufactured by Corbion purac.

  Next, test examples will be described. The excretion-type multidrug-resistant strains used in the following test examples are all strains that are maintained and managed in-house, and the Patented Microorganisms Depositary Center (NPMD) (NITE) (National Institute of Technology and Evaluation) (No. 122, Room 2-5-8 Kazusa Kamatari, Kisarazu City, Chiba Prefecture). The NITE deposit number is written for each strain name together with the in-house management code.

Test Example 1 Pest Control Test Against Efflux Multidrug-Resistant Wheat Leaf Blight Fungus (Zymoseptria tritici) The compound (1) and tolnaftate were each diluted with dimethyl sulfoxide at a predetermined concentration. After dispensing 1 μl of a drug solution containing each test compound into a titer plate (96 well), the wheat leaf blight fungus (an excretion-type multidrug-resistant strain (strain name: St106-6) or a wild-type strain) was previously separated. 150 μl of potato decoction liquid medium (PDB medium) inoculated with live spores was dispensed, and the plate was cultured at 18 ° C. for 4 days to grow each wheat leaf blight fungus. The growth of each wheat leaf blight fungus was measured by the absorbance of the control (treatment group), and the chemical solution was replaced with dimethyl sulfoxide to obtain a wild-type strain or an excretion-type multidrug-resistant wheat leaf blight strain similarly to the treatment group. The grown sections were designated as non-treated sections, and their growth degree was investigated (untreated section) Based on the growth degree, the efficacy was calculated by the following “Equation 1”, and the emission type of each compound was calculated. EC ₅₀ values were calculated for each of resistant strains and the wild type strain. Then, as shown in the following "equation 2", EC ₅₀ values for emptying multidrug resistant strains, divided with an EC ₅₀ value against the wild type strain was determined and _{EC 50} values ratio Te. the results are shown in Table 3. _{EC 50} Nehi tolnaftate was high and 19, _{EC 50} Nehi of the compound (1) was as low as 1.0. this From this, it was confirmed that the present compound (1) shows the same controlling activity as that against wild-type strains even on excretion-type multidrug-resistant strains.
"Equation 1"
Efficacy = 100 × (XY) / X
X: Growth rate of the fungus in the untreated area Y: Growth rate of the fungus in the treated area [Equation 2]
EC ₅₀ values ratio = _{The EC 50} values for _{The EC 50} values / wild-type strain for emptying multidrug-resistant strains

Test Example 2 Control test against efflux-type multidrug-resistant grape gray mold fungus (Botrytis cinerea) The present compound (1), fludioxonil (Fludioxonil), and tolnaftate (Tolnaftate) were each diluted with dimethyl sulfoxide at a predetermined concentration. After dispensing 1 μl of the drug solution containing each test compound into a titer plate (96 wells), the grape mold fungus [excretion type multidrug resistant strain (excretion type multidrug resistant strain 1: ABC transporter overexpressing strain) was prepared in advance. (Strain name: NITE deposit number (NITE BP-02676), in-house management code (Bc-56)), efflux type multidrug resistant strain 2: MFS transporter overexpressing strain (strain name: NITE deposit number (NITE BP-02678) ), In-house management code (Bc-107)), efflux-type multidrug-resistant strain 3: ABC transporter and MFS transporter overexpressing strain (strain name: NITE accession number (NITE BP-02677), in-house management code (Bc-107)) 103)))] or a potato decoction liquid medium (PDB medium) inoculated with conidia of conidia of a wild-type strain. ) Was dispensed 150μl minutes. After the plate was cultured at 18 ° C. for 2 days to grow each grape mold, each well of the titer plate was measured for the growth rate of each grape mold at an absorbance of 600 nm (treatment area). . On the other hand, in the same manner as in the treated group, the group in which the chemical solution was replaced with dimethyl sulfoxide and in which the wild-type strain or the excretion-type multidrug-resistant grape gray mold fungus strain was grown was defined as an untreated group, and the growth rate was examined (untreated group). Ward). Based on the degree of growth, the potency was calculated according to the above “Equation 1”, and the EC ₅₀ value of each compound for each of the excretion-type multidrug-resistant strain and the wild-type strain was calculated. Further, the EC ₅₀ value ratio was determined by the above “Equation 2”. Table 4 shows the results. The EC ₅₀ value ratio of fludioxonil was as high as 23, 14, and 43, and the EC ₅₀ value ratio of tolnaftate was all higher than 4.5, but the EC ₅₀ value ratio of the present compound (1) was 0. .62, 1.2, and 0.58. From this, it was confirmed that the present compound (1) shows the same control activity as that against wild-type strains even against excretion-type multidrug-resistant strains.

Claims (7)

The following equation (1):

A method for controlling a plant disease caused by an excretion-type multidrug-resistant bacterium, comprising a step of treating a plant or a soil for cultivating the plant with an effective amount of a pyridazine compound represented by the formula:   2. The efflux-type multidrug-resistant bacterium according to claim 1, wherein the bacterium has acquired resistance to a plant disease controlling agent by overexpression of at least one membrane transporter selected from the group consisting of an ABC transporter and an MFS transporter. Method of controlling plant diseases.   The method for controlling plant diseases according to claim 1 or 2, wherein the plant diseases are at least one plant disease selected from the group consisting of wheat diseases and grape diseases.   The method for controlling plant diseases according to claim 1 or 2, wherein the efflux-type multidrug-resistant bacterium is at least one efflux-type multidrug-resistant bacterium selected from the group consisting of wheat leaf blight and grape gray mold.   An efflux-type multidrug-resistant bacterium is derived from a mutation in a gene encoding a target protein of the plant disease control agent with respect to at least one plant disease control agent selected from the group consisting of a respiratory inhibitor and a sterol biosynthesis inhibitor. The method for controlling plant diseases according to any one of claims 1 to 4, wherein the method is an efflux-type multidrug-resistant bacterium having tolerance to the target protein and / or resistance derived from overexpression of the target protein.   The method for controlling plant diseases according to any one of claims 1 to 5, wherein the step of treating the plant or the soil where the plant is cultivated is a step of treating a seed. The following formula (1) for controlling plant diseases caused by excretion-type multidrug-resistant bacteria:

Use of a pyridazine compound represented by