KR102545866B1 - Methods for Controlling Discharged Multi-drug Resistant Plant Diseases - Google Patents

Abstract

로 나타내는 피리다진 화합물의 유효량을 식물 또는 식물을 재배하는 토양에 처리하는 공정을 포함하는, 배출형 다제 내성 식물 병해의 방제 방법을 제공한다.The present invention, having an excellent effect on the discharge-type multi-drug resistant plant disease, the following formula (1):

Provided is a method for controlling multiple drug-resistant plant diseases, including a step of treating plants or soil in which plants are grown with an effective amount of a pyridazine compound represented by .

Description

Methods for Controlling Discharged Multi-drug Resistant Plant Diseases

This patent application claims priority and benefits under the Paris Convention based on Japanese Patent Application No. 2017-091192 (filed on May 1, 2017). to be accepted in

The present invention relates to a method for controlling discharge-type multidrug-resistant plant diseases.

BACKGROUND OF THE INVENTION [0002] In recent years, due to the multi-use of plant disease control agents, bacteria that have acquired resistance to a plurality of plant disease control agents that have been used so far have appeared. It is believed that these resistance-acquiring bacteria have acquired resistance to a plurality of plant disease control agents by mutation of the action point (target protein) of the plant disease control agent or acquisition of decomposition ability of the plant disease control agent.

On the other hand, in recent years, the existence of bacteria that have acquired resistance to not only the plant disease control agents that have been used so far but also other plant disease control agents has been newly reported due to the acquisition of the extracellular excretion ability of plant disease control agents. (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 is a plant disease caused by bacteria that have acquired resistance to plant disease control agents by acquiring the extracellular excretion ability of plant disease control agents (hereinafter sometimes referred to as excretion-type multi-drug resistant bacteria) (hereinafter, It is an object to provide a control method for (sometimes described as discharge-type multidrug-resistant plant disease).

The inventors of the present invention, as a result of examining to find out a method having excellent control effect against excretory multi-drug resistant plant diseases, found that the pyridazine compound represented by the following formula (1) has an excellent control effect against excretory multi-drug resistant plant diseases. I figured it out.

That is, this invention is as follows.

[1] Equation (1) below:

[Formula 1]

A method for controlling plant diseases caused by excretion-type multidrug-resistant bacteria, comprising a step of treating plants or soil in which plants are grown with an effective amount of a pyridazine compound represented by .

[2] The plant according to [1], wherein the excretory multi-drug resistant bacteria are bacteria that have acquired resistance to plant disease control agents by over-expression of at least one membrane transporter selected from the group consisting of ABC transporters and MFS transporters. Disease control method.

[3] The plant disease control method according to [1] or [2], wherein the plant disease is at least one plant disease selected from the group consisting of wheat disease and grape disease.

[4] The plant disease control method according to [1] or [2], wherein the excretory multidrug-resistant bacteria is at least one excretory multidrug-resistant bacterium selected from the group consisting of wheat leaf blight and grape gray mold.

[5] Excretory multidrug-resistant bacteria are resistant to at least one plant disease control agent selected from the group consisting of respiratory inhibitors and sterol biosynthesis inhibitors, derived from mutations in the gene encoding the target protein of the plant disease control agent and / Or the method for controlling a plant disease according to any one of [1] to [4], which is an excreted multi-drug resistant bacterium having resistance derived from overexpression of the target protein.

[6] The plant disease control method according to any one of [1] to [5], wherein the step of treating the plant or the soil for cultivating the plant is a step of treating the seed.

[7] For the control of plant diseases caused by excretory multi-drug resistant bacteria, the following formula (1):

[Formula 2]

Use of a pyridazine compound represented by

According to the present invention, it is possible to control discharge-type multi-drug resistant plant diseases.

The method for controlling multiple-drug-resistant plant diseases of the present invention (hereinafter referred to as the method of the present invention) is to cultivate plants or plants in an effective amount of the pyridazine compound represented by the formula (1) (hereinafter referred to as the present compound (1)). It includes the process of treating the soil to

First, this compound (1) is demonstrated.

This compound (1) has the following formula (1):

[Formula 3]

It is a pyridazine compound represented by , and is described, for example, in International Publication No. 2005/121104, and can also be produced by the method described therein.

As the form in which the present compound (1) is used, the present compound (1) alone may be used, but usually the present compound (1) is mixed with an inert carrier, and if necessary, a surfactant or other auxiliary agent for formulation is added Thus, formulations such as wettable powders, granulated wettable powders, flowables, granules, powders, dry floorables, emulsions, aqueous liquids, oils, smokers, aerosols, microcapsules (hereinafter, It is referred to as this formulation) and used after being formulated into a formulation. For example, in these present formulations, the present compound (1) is usually contained in an amount of 0.1 to 99% by weight, preferably 0.2 to 90% by weight, and more preferably 5 to 50% by weight, based on the total weight of the formulation. . These preparations can be used as a release-type, multi-drug resistant plant disease control agent with the addition of other inactive ingredients or as is.

Solid carriers and liquid carriers are mentioned as an inactive carrier used at the time of formulation.

Examples of the solid carrier include clays (eg, kaolin, diatomaceous earth, synthetic hydrous silicon oxide, fubasami clay, bentonite, acid clay), talc, and other inorganic minerals (eg, sericite). , quartz powder, sulfur powder, activated carbon, calcium carbonate, and hydrated silica).

As the liquid carrier, for example, water, alcohols, ketones (eg, acetone, methyl ethyl ketone, cyclohexanone), aromatic hydrocarbons (eg, benzene, toluene, xylene, ethylbenzene, methyl naphthalene), aliphatic hydrocarbons (eg, n-hexane, kerosene), esters, nitriles, ethers, acid amides, and halogenated hydrocarbons.

Examples of the surfactant include alkyl sulfate esters, alkyl sulfonates, alkylaryl sulfonates, alkyl aryl ethers and polyoxyethylenates thereof, polyoxyethylene glycol ethers, polyhydric alcohol esters, and sugar alcohol derivatives. can

Other auxiliary agents for preparation include, for example, a fixing agent, a dispersing agent, and a stabilizer. Specifically, casein, gelatin, polysaccharides (eg, starch, gum arabic, cellulose derivatives, alginic acid), lignin derivatives, bentonite, Sugars, synthetic water-soluble polymers (e.g. polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids), PAP (isopropyl phosphate), BHT (2,6-di-tert-butyl-4-methylphenol) , BHA (a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), fatty acids or their esters.

Moreover, you may further mix and use this formulation with various oils, such as mineral oil and vegetable oil, and/or other surfactant. 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), Silwet L-77 (registered trademark), BreakThru ( (registered trademark), SundanceII (registered trademark), Induce (registered trademark), Penetrator (registered trademark), AgriDex (registered trademark), Lutensol A8 (registered trademark), NP-7 (registered trademark), Triton (registered trademark), Nufilm (registered trademark), Emulgator NP7 (registered trademark), Emulad (registered trademark), TRITON X 45 (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 present compound (1) may be used in combination with one or more compounds selected from other plant disease control active compounds and insecticidal active compounds.

The method of the present invention is carried out by treating a plant or the soil in which the plant is grown with an effective amount of the present compound (1). As such a plant, the foliage of a plant, the seed of a plant, and the bulb of a plant are mentioned, for example. In addition, a bulb here means a bulbous root, a bulbous root, a rhizome, a tuber, a tuber root, and a root body.

The method of application of the present compound (1) is not particularly limited as long as it is in a form in which the present compound (1) can be applied substantially. Treatment for plantation such as treatment, treatment for seeds such as seed disinfection, and the like are exemplified.

As such a foliage treatment, a method of treating the surface of a cultivated plant by, for example, foliage spreading and stem spreading is exemplified.

As such a root treatment, for example, a method of immersing the whole or root of a plant in a chemical solution containing the present compound (1), and a solid preparation containing the present compound (1) and a solid carrier of the plant A method of attaching to the root can be mentioned.

Examples of such soil treatment include soil spreading, soil mixing, and chemical irrigation to the soil.

Such seed treatment includes, for example, treatment of the seeds or bulbs of plants to be protected from plant diseases with the present compound (1), and specifically, for example, those containing the present compound (1) A spray treatment in which a mixture of formulation and water is sprayed on the surface of seeds or bulbs in a misty state, a coating applied to seeds or bulbs by adding a small amount of water to a wet agent, emulsion or flowable agent containing this compound (1) or as it is A soaking treatment, an immersion treatment in which seeds are immersed in a solution of the present compound (1) for a certain period of time, a film coating treatment, and a pellet coating treatment are exemplified.

In the method of the present invention, the treatment amount of the present compound (1) varies depending on the type of plant to be treated, the type and frequency of occurrence of plant diseases to be controlled, the type of formulation, treatment time, treatment method, treatment location, weather conditions, etc. However, in the case of application to the foliage of plants or to the soil in which plants are grown, the amount of this compound (1) per 1000 m 2 is usually 1 to 500 g, preferably 5 to 50 g.

Emulsions, hydration agents, flowable agents, etc. are usually treated by diluting with water and spraying. In this case, the concentration of the present compound (1) is usually 0.0005 to 2% by weight, preferably 0.001 to 1% by weight. Powders, granules, etc. are usually treated as they are without dilution.

In the present specification, excretion-type multi-drug resistant bacteria are expressed in excess of various membrane transporters present on the cell membrane, and the excretion pump function of excreting the plant disease control agent introduced into the cell to the outside of the cell is enhanced, thereby increasing the number of plant disease control agents refers to organisms that are resistant to Examples of the membrane transporter include, but are not limited to, ABC transporters and MFS transporters. In the present specification, ABC transporters refer to ATP-binding cassette transporters, and MFS transporters refer to major facilitator superfamily transporters. 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, for example, by quantitative reverse transcription polymerase chain reaction (qRT-PCR). More specifically, in the following known documents, the measuring method is disclosed.

Environmental Microbiology. 2015; 17(8), 2805-2823.

Pest Management Science. 2001; 57(5): 393-402.

PLoS Pathogen. 2009; Dec ; 5(12): e1000696.

Excretory multidrug-resistant bacteria should just show resistance to plant disease control agents as a result of excessive expression of the membrane transporter regardless of the amount of mRNA measured. The measured amount of mRNA may be, for example, 20 times, 50 times, or more than 100 times the amount of wild-type bacterial mRNA. Alternatively, as described later in this specification, the EC ₅₀ value for the excretory multi-drug resistant strain is divided by the EC ₅₀ value for the wild-type strain to obtain the EC ₅₀ value ratio, and tolnaftate known as an indicator of excretory multi-drug resistant bacteria is used. Thus, the EC ₅₀ value ratio of tolnaftate is 3 times or more, preferably 10 times or more.

The method of the present invention is applied to control plant diseases caused by excretory multi-drug resistant bacteria. As described above, the method of the present invention is carried out by treating a plant or the soil in which the plant is grown with an effective amount of the present compound (1). The plant is a plant in which plant diseases caused by excretion-type multidrug-resistant bacteria occur, and plants in which plant diseases caused by excretory-type multidrug-resistant bacteria may occur.

Excretory multidrug-resistant bacteria may have resistance derived from mutations in genes encoding target proteins of various plant disease control agents and/or resistance derived from overexpression of the target proteins. In addition, the target protein having a mutation or excessive expression in the gene may be of multiple types. However, they do not have resistance to the present compound (1) due to mutation of the gene encoding the target protein of the present compound (1).

The various plant disease control agents include, for example, nucleic acid synthesis inhibitors (eg, phenylamide-based fungicides, acylamino acid-based fungicides), mitosis and cell division inhibitors (eg, MBC fungicides, N -phenylcarbamate bactericides), respiratory inhibitors (eg QoI bactericides, QiI bactericides, SDHI bactericides), inhibitors of amino acid synthesis and protein synthesis (eg anilinopyrimidine bactericides), signal transduction inhibitors (eg For example, phenylpyrrole disinfectants, dicarboximide disinfectants), inhibitors of lipid synthesis and cell membrane synthesis (eg phosphorothiolate disinfectants, dithiolane disinfectants, aromatic hydrocarbon disinfectants, heteroaromatic disinfectants, carbamate disinfectants) , sterol biosynthesis inhibitors (eg, triazole-based DMI disinfectants, hydroxyanilide-based disinfectants, aminopyrazolinone-based disinfectants), cell wall synthesis inhibitors (eg, polyoxine-based disinfectants, carboxylic acid amide-based disinfectants), melanin synthesis inhibitors (eg, MBI-R disinfectant, MBI-D disinfectant, MBI-P disinfectant), and other disinfectants (eg, cyanoacetamide oxime disinfectant, phenylacetamide disinfectant). It is preferably at least one plant disease control agent selected from the group consisting of respiratory inhibitors and sterol biosynthesis inhibitors. Examples of mutation points of genes encoding each target protein in each plant pathogen include those shown in Table 1 below.

Excretion-type multi-drug resistant bacteria exhibit excretion-type multiple drug resistance, and at least one genetic mutation point selected from the group consisting of the following (A), (B), (C-1), (C-2) and (C-3) It may be a wheat leaf bacilli having.

(A) Genes encoding cytochrome b: F129L, G137R, G143A;

(B) Genes encoding Cyp51: L50S, D107V, D134G, V136A/C/G, Y137F, M145L, N178S, S188N, S208T, N284H, H303Y, A311G, G312A, A379G, I381V/Δ, A410T, G412A, Y4 59C /D/N/S/P/Δ, G460D/Δ, Y461D/H/S, V490L, G510C, N513K, S524T ;

(C-1) Genes encoding SDHB: 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) Genes encoding SDHD: I50F, M114V, D129E.

Excretion-type multidrug-resistant bacteria exhibit excretion-type multiple drug resistance and have at least one genetic mutation point selected from the group consisting of the following (D), (E-1), (E-2) and (E-3) grape gray It may be a fungal pathogen.

(D) Gene encoding cytochrome b: G143A;

(E-1) Genes encoding SDHB: P225H/F/L/T, N230I, H272L/R/V/Y;

(E-2) Genes encoding SDHC: P80H/L, A85V;

(E-3) Gene encoding SDHD: H132R.

This compound (1) can be used as a control agent for discharge-type multi-drug resistant plant diseases in agricultural fields such as fields, rice fields, lawns, orchards. The method of the present invention is applied to agricultural lands for cultivating "plants" and the like exemplified below.

Agricultural crops: corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, buckwheat, sugar beet, rapeseed, sunflower, sugar cane, tobacco, etc.

Vegetables: solanaceous vegetables (e.g. eggplant, tomato, bell pepper, pepper, potato), gourd vegetable (e.g. cucumber, zucchini, zucchini, watermelon, melon), cruciferous vegetable (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage) , mustard, broccoli, cauliflower, etc.), Asteraceae vegetables (burdock, crown daisy, artichoke, lettuce, etc.), liliaceae vegetables (leeks, onions, garlic, asparagus, etc.), parsley vegetables (carrots, parsley, celery, parsnips, etc.) ), Goat and vegetables (spinach, chard, etc.), Lamiaceae vegetables (perilla, mint, basil, etc.), strawberries, sweet potatoes, yams, taro, etc.;

flowers,

houseplant,

grass,

Fruit trees: Phosphorus (apple, pear, Japanese pear, quince, quince, etc.), stone fruit (peach, plum, nectarine, plum, cherry, apricot, prune, etc.), citrus (tangerine, orange, lemon, lime, grapefruit, etc.) etc.), nuts (chestnuts, walnuts, hazelnuts, almonds, pistachios, cashews, macadamia nuts, etc.), liquid fruits (blueberries, cranberries, blackberries, raspberries, etc.), grapes, persimmons, olives, loquats, bananas, coffee, date palm, coco palm, etc.;

Trees other than fruit trees: tea, mulberry, flower trees, roadside trees (ash, birch, American dogwood, eucalyptus, ginkgo, lilac, maple, oak, poplar, gourd, Taiwanese, sycamore, zelkova, Japanese Arborvitae, Fir, Hem-Fir, Juniper, Pine, Spruce and Yew), etc.

Genetically recombinant crops are also included in the above "plant".

Exhaust multidrug-resistant plant diseases that can be controlled by the present compound (1) include, for example, plant diseases caused by plant pathogens such as filamentous fungi, and specifically include the following, It is not limited to these.

Diseases of rice: Magnaporthe grisea, Cochliobolus miyabeanus, Rhizoctonia solani;

Diseases of wheat: powdery mildew (Erysiphe graminis), rust (Puccinia striiformis, P. graminis, P. triticina), red snow blotch (Micronectriella nivale, M. majus), snowy mildew (Typhula sp.), eye disease (Pseudocercosporella herpotrichoides) );

Diseases of barley: powdery mildew (Erysiphe graminis), rust (Puccinia striiformis, P. graminis, P. hordei), rhynchosporium secalis (Pyrenophora teres), spot disease (Cochliobolus sativus), half leaf (Pyrenophora graminea) ), Ramularia collo-cygni, Rhizoctonia solani;

Diseases of corn: rust (Puccinia sorghi), southern rust (Puccinia polysora), black blotch (Setosphaeria turcica), tropical rust (Physopella zeae), sesame spot (Cochliobolus heterostrophus), gray blot (Cercospora zeae-maydis);

Diseases of cotton: White mold disease (Ramuraria areola);

Diseases of coffee: rust (Hemileia vastatrix), leaf spot disease (Cercospora coffeicola);

Diseases of sugarcane: rust (Puccinia melanocephela, Puccinia kuehnii);

Diseases of sunflower: Rust (Puccinia helianthi);

Diseases of citrus fruits: black spot (Diaporthe citri), window disease (Elsinoe fawcetti), fruit rot (Penicillium digitatum, P. italicum);

Diseases of apples: Monilinia mali, powdery mildew (Podosphaera leucotricha), black star disease (Venturia inaequalis), brown disease (Diplocarpon mali), Botryosphaeria berengeriana;

Diseases of the pear: black-star disease (Venturia nashicola, V. pirina), red-star disease (Gymnosporangium haraeanum);

Peach diseases: Monilinia fructicola, black star disease (Cladosporium carpophilum), Phomopsis sp.;

Diseases of grapes: Black head disease (Elsinoe ampelina), powdery mildew disease (Uncinula necator), rust disease (Phakopsora ampelopsidis), black rot disease (Guignardia bidwellii);

Diseases of Persimmon: Deciduous leaf (Cercospora kaki, Mycosphaerella nawae);

Diseases of Cucurbitaceae: Powdery mildew (Sphaerotheca fuliginea), vine blight (Didymella bryoniae), brown spot (Corynespora cassiicola);

Diseases of tomatoes: leaf mold (Cladosporium fulvum), plum disease (Pseudocercospora fuligena), powdery mildew (Leveillula taurica);

Diseases of eggplant: Phomopsis vexans, powdery mildew (Erysiphe cichoracearum);

Green onion disease: Rust (Puccinia allii);

Diseases of soybean: purpura (Cercospora kikuchii), rust (Phakopsora pachyrhizi), brown spot (Corynespora cassiicola), leaf spot (Rhizoctonia solani), brown spot (Septoria glycines), spot disease (Cercospora sojina), powdery mildew (Microspaera diffusa);

Diseases of kidney beans: Rust (Uromyces appendiculatus);

Peanut diseases: black shovel (Cercospora personata), brown blight (Cercospora arachidicola);

Diseases of peas: Powdery mildew (Erysiphe pisi);

Strawberry disease: powdery mildew (Sphaerotheca humuli);

Diseases of sugar beet: brown spot (Cercospora beticola), leaf spot (Thanatephorus cucumeris), root disease (Thanatephorus cucumeris);

Diseases of roses: Powdery mildew (Sphaerotheca pannosa);

Diseases of chrysanthemum : Septoria chrysanthemi-indici;

Diseases of onions: Vitiligo leaf blight (Botrytis cinerea, B. byssoidea, B. squamosa), gray rot (Botrytis alli), microbiological rot (Botrytis squamosa);

Several crop diseases: Gray mold (Botrytis cinerea);

Lawn diseases: Brown patch disease and large patch disease (Rhizoctonia solani);

Banana disease: Sigatoka disease (Mycosphaerella fijiensis, Mycosphaerella musicola).

Example

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

Examples of formulations used in the method of the present invention are shown. In addition, in a formulation example, a part shows a part by weight.

Formulation Example 1

A wettable powder is obtained by sufficiently pulverizing and mixing 50 parts of this 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 this compound (1) and 1.5 parts of sorbitan trioleate are mixed with 28.5 parts of water containing 2 parts of polyvinyl alcohol, pulverized by wet pulverization, and then 0.05 part of xanthan gum and aluminum magnesium silicate are mixed therein. 40 parts of water containing 0.1 part is added, and further 10 parts of propylene glycol are added and stirred and mixed to obtain a flowable formulation.

Formulation Example 3

A powder agent is obtained by sufficiently pulverizing and mixing 2 parts of this compound (1), 88 parts of kaolin clay, and 10 parts of talc.

Formulation Example 4

An emulsion is obtained by sufficiently mixing 5 parts of this compound (1), 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate, and 75 parts of xylene.

Formulation Example 5

2 parts of this compound (1), 1 part of synthetic hydrous silicon oxide, 2 parts of calcium ligninsulfonate, 30 parts of bentonite, and 65 parts of kaolin clay were sufficiently pulverized and mixed, then water was added, sufficiently kneaded, and granulated and dried. , get a grain

Formulation Example 6

20 parts of this compound (1); A flowable preparation is obtained by mixing 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate ammonium salt (weight ratio 1:1) and water to make the total amount 100 parts, and processing using a grinder.

Formulation Example 7

The raw materials shown in Table 2 were mixed in the weight ratio shown in Table 2, stirred until a uniform solution was obtained, and respective formulations were obtained. In addition, the number in a table|surface represents a weight part.

The product names listed in Table 2 above are as follows.

Agnique AMD810: a mixture of N,N-dimethyloctanamide and N,N-dimethyldecanamide, manufactured by BASF;

Hallcomid M-8-10: A mixture of N,N-dimethyloctaneamide and N,N-dimethyldecanamide, manufactured by Stepan;

Agnique AMD3L: N,N-dimethyllactamide, manufactured by BASF;

Sorbeso 200ND: An aromatic hydrocarbon, mainly C11-14 alkylnaphthalene, manufactured by ExxonMobil Chemical;

Calsogen 4814: Calcium salt of dodecylbenzenesulfonate, manufactured by Clariant;

ATPLUS245: polyoxyethylene polyoxypropylene alkyl ether, manufactured by Croda;

Brij O3: polyoxyethylene oleyl ether, HLB: 7, manufactured by Croda;

Atlas G5002L: butyl block copolymer manufactured by Croda;

Toximul 8323: polyoxyethylene polyoxypropylene block copolymer, manufactured by Stepan;

Rhodiasolv Polarclean: 80 to 90% by weight of methyl 5-(dimethylamino)-2-methyl-5-oxopentanoic acid (however, the total amount is 100% by weight), manufactured by Solvainica;

PURASOLV ML: L-methyl lactate, manufactured by Corbion Purac;

PURASOLV EL: L-ethyl lactate, manufactured by Corbion purac.

Next, a test example is shown. All of the excretory multidrug-resistant strains used in the following test examples are strains maintained and managed in-house, and the Patent Microorganism Depository Center (NPMD) within the National Institute for Product Evaluation and Technology (NITE) (Kazusakamatari, Kisarazu City, Chiba Prefecture) 2-5-8 Room 122) on April 10, 2018. Each strain name is described along with the in-house management code and the NITE accession number.

Test Example 1 Control test for discharge type multi-drug resistant wheat leaf blight (Zymoseptoria tritici)

The compound (1) and tolnaftate were each diluted in dimethyl sulfoxide to a predetermined concentration. After dispensing 1 μl of the chemical solution containing each test compound into a titer plate (96 well), conidia of a wheat leaf fungus (discharge type multi-drug resistant strain (strain name: St 106-6) or wild type strain in advance) 150 μl of the potato broth (PDB medium) inoculated with the spores was dispensed, and the plate was incubated at 18 ° C. for 4 days to propagate each wheat leaf blight, and then each well of the titer plate was stained with an absorbance of 600 nm. On the other hand, the growth rate of each wheat leaf blight bacteria was measured (treated group). Based on the growth rate, the efficacy was calculated by the following "Equation 1", and the EC ₅₀ value for each of the excretory multi-drug resistant strain and the wild type strain of each compound was calculated. , As shown in "Equation 2" below, the EC ₅₀ value for the multiple-drug resistant strain was divided by the EC ₅₀ value for the wild-type strain to obtain the EC ₅₀ value ratio. The results are shown in Table 3. Although the EC ₅₀ value ratio was as high as 19, the EC ₅₀ value ratio of the present compound (1) was as low as 1.0.From this, the present compound (1) has a control activity equivalent to the control activity against the wild-type strain against the excretory multi-drug resistant strain. It was confirmed that the indicated

"Formula 1"

Effect = 100 × (X - Y)/X

X: growth rate of bacteria in the untreated area

Y: growth rate of bacteria in the treatment group

"Formula 2"

EC ₅₀ value ratio = EC ₅₀ value for excretory multi-drug resistant strain/EC ₅₀ value for wild type strain

Test Example 2 Control test for discharge type multi-drug resistant grape gray mold (Botrytis cinerea)

Compound (1), Fludioxonil and Tolnaftate were each diluted in dimethyl sulfoxide to a predetermined concentration. After dispensing 1 µl of the chemical solution containing each test compound into a titer plate (96 well), grape gray mold disease [excretion-type multidrug-resistant strain (excretion-type multidrug-resistant strain 1: ABC transporter overexpression strain (strain name: strain name: NITE accession number (NITE BP-02676), internal management code (Bc-56)), excretory multi-drug resistant strain 2: MFS transporter overexpressing strain (strain name: NITE accession number (NITE BP-02678), internal management code ( Bc-107)), excretory multi-drug resistant strain 3: ABC transporter and MFS transporter overexpressing strain (strain name: NITE accession number (NITE BP-02677), in-house management code (Bc-103))) or wild-type strain 150 μl of potato juice liquid medium (PDB medium) inoculated with conidia was dispensed. This plate was incubated at 18°C for 2 days to propagate each grape gray mold, and then the growth rate of each grape gray mold was measured by absorbance at 600 nm in each well of the titer plate (treatment group). On the other hand, the drug solution was changed to dimethyl sulfoxide, and the wild-type strain or the discharge-type multi-drug resistant grape gray mold strain was grown in the same way as the treatment group as each untreated group, and the growth rate was investigated (untreated group). Based on the growth rate, the efficacy was calculated by the above "Equation 1", and the EC ₅₀ value for each of the excretory multi-drug resistant strain and wild-type strain of each compound was calculated. In addition, the EC ₅₀ value ratio was obtained by the above “Formula 2”. The results are shown in Table 4. The EC ₅₀ values of fludioxonil were as high as 23, 14, and 43, and the EC ₅₀ values of tolnaftate were all higher than 4.5, but the EC ₅₀ values of the present compound (1) were 0.62, 1.2, and 0.58. was as low as From this, it was confirmed that the present compound (1) exhibits a control activity equivalent to that against a wild-type strain against an excretory multi-drug resistant strain.

Claims (7)

Equation (1) below:

A method for controlling plant diseases caused by excretion-type multidrug-resistant bacteria, comprising a step of treating plants or soil in which plants are grown with an effective amount of a pyridazine compound represented by . According to claim 1,
A plant disease control method, wherein the excretory multidrug-resistant bacteria are bacteria that have acquired resistance to plant disease control agents by overexpression of at least one membrane transporter selected from the group consisting of ABC transporters and MFS transporters. According to claim 1 or 2,
A method for controlling plant diseases, wherein the plant disease is at least one plant disease selected from the group consisting of wheat diseases and grape diseases. According to claim 1 or 2,
A method for controlling a plant disease, wherein the excretion type multi-drug resistant bacteria is at least one excretion type multi-drug resistant bacterium selected from the group consisting of wheat leaf blight and grape gray mold. According to claim 4,
Excretory multidrug-resistant bacteria are resistant to at least one plant disease control agent selected from the group consisting of respiratory inhibitors and sterol biosynthesis inhibitors, and/or resistance derived from mutations in the gene encoding the target protein of the plant disease control agent and/or the target. A method for controlling plant diseases, which is an excretory multi-drug resistant bacterium having resistance derived from protein overexpression. According to claim 1,
A method for controlling a plant disease wherein the step of treating a plant or soil for cultivating the plant is a step of treating a seed. delete