WO2004039156A1

WO2004039156A1 - Fungicidal compositions for the control of paddy rice diseases

Info

Publication number: WO2004039156A1
Application number: PCT/JP2003/013850
Authority: WO
Inventors: Takeshi Teraoka; Makoto Matsumura
Original assignee: Meiji Seika Kaisha, Ltd.
Priority date: 2002-10-30
Filing date: 2003-10-29
Publication date: 2004-05-13
Also published as: TW200418384A; KR100764948B1; AR041728A1; JPWO2004039156A1; CN1327768C; AU2003280600A1; TWI320305B; JP4558496B2; CN1708225A; KR20050059321A

Abstract

Fungicidal compositions effective in the control of paddy rice diseases, containing as the active ingredients both a compound represented by the general formula (1) or an acid addition salt thereof and at least one member selected from among strobilurin insecticides: (1) wherein R is hydrogen, -COR1, -COOR1 (wherein R1 is alkyl having 1 to 4 carbon atoms), -COCH2OCH3, or -COCH2OCOCH3.

Description

Ming Fungicidal composition for controlling rice disease

[Background of the invention]

Field of the invention

TECHNICAL FIELD The present invention relates to a bactericidal composition exhibiting an excellent control effect against an excellent rice disease. More specifically, the present invention relates to a fungal rice disease including rice blast.

Itoda

The present invention relates to a bactericidal composition showing an excellent control effect on germs.

Related technology

WO 01/92231 (International Publication Date: 2001/12/06) by the present applicant discloses a compound represented by the following formula (1) or an acid addition salt thereof having excellent bactericidal activity. ing,:

Wherein R is a hydrogen atom, —COIT, —COOR ¹ (where R ¹ is an alkyl group having 1 to 4 carbon atoms), —COCH ₂ OCH ₃ or one COCH ₂ OCOCH ₃ . It also describes the physicochemical properties of this compound and its control effect on rice blast. Furthermore, here, this compound not only has an excellent therapeutic effect on rice blast, but also has excellent residual and preventive effects, which means that this compound has a therapeutic effect on existing rice blast control agents. It also states that they are different.

The mechanism of action of the compound of formula (1) has not yet been clarified. However, it shows a control effect against bacteria resistant to kasugamycin, organophosphates, and stomatal viruline compounds, and shows bactericidal activity without inhibiting melanin biosynthesis in the medium. Because of that, It is presumed to have a different mechanism of action from existing rice blast control agents.

Excellent control or high bactericidal activity against multiple fungal rice diseases including rice blast, or various fungal diseases or pathogenic bacteria that cause problems in cultivation of wheat, vegetables and fruit trees. As the indicated compound, a strobilurin-based fungicide compound has been reported. Regarding the fact that strobilurin compounds have such an excellent control effect, and the mechanism of their action, for example, see the Agrochemical Handbook, 2001 edition (2001, published by the Japan Plant Protection Association), and It is described in the general contract test report (issued by the Japan Plant Protection Association).

Rice blast is the most damaging disease in rice cultivation. Blast is a type of filamentous fungus and is a plant disease caused by the infestation of Pyricularia spp. Many excellent control agents and methods for controlling rice blast have been reported so far.

However, depending on weather conditions such as cold damage and long rainy season, and cultivation conditions such as inadequate management in raising seedlings and fertilizers, rice blast can occur even when such a pesticide is used. A case was also found. For this reason, the development of a control agent having a more excellent control effect is desired. In recent years, as farmers have been part-time jobs and farmers are aging more and more, there is a need for technologies to extend the disease control period, reduce the frequency of spraying, and reduce labor. In addition, for the purpose of labor saving and reducing the amount of applied pesticides, there is a demand for the development of a drug that can simultaneously control multiple diseases.

[Overview of the invention]

The present inventors have recently evaluated the combined effect of the above-mentioned activities and the durations of the activities, and found that the compound of the above formula (1) (2,3-dimethyl-1 6-t-butyl-1 A mixed composition comprising 8-fluoro-4-quinolinol derivative) and at least one compound selected from stomatal bilulin-based insecticides not only does not impair the activity of each component but also has a synergistic effect. It was found that it exerted an excellent control effect on rice blast. At this time, the composition is applied not only when it is applied to rice blast, which is a typical rice disease, but also when it is applied at an appropriate time, and the application time is delayed. In these cases, it was found that even at low doses, excellent control effects were exhibited over a long period of time at low doses. The present invention is based on such findings.

Accordingly, an object of the present invention is to provide an agent having an excellent control effect on paddy rice diseases, which is capable of exhibiting an excellent control effect over a long period at a low dose even when the application time is delayed. I do.

The bactericidal composition according to the present invention has the following formula (1):

Where R is a hydrogen atom, one COR ^ -COOR ¹ (where R ¹ is an alkyl group having 1 to 4 carbon atoms), — COCH ₂ 〇CH ₃ or one CO CH ₂ OCOCH ₃

Or a compound or an acid addition salt thereof,

At least one compound selected from strobilurin insecticides;

As an active ingredient.

The method for controlling rice disease according to the present invention comprises applying an effective amount of the bactericidal composition to a region to be treated.

According to the present invention, there is provided use of the bactericidal composition for producing an agent for controlling rice disease.

The bactericidal composition according to the present invention is obtained by mixing two kinds of compounds having different action mechanisms and different bactericidal spectra. The bactericidal composition according to the present invention can be used for not only rice blast, butter blight, sesame leaf blight fungus, ear blight caused by fungi, etc., discolored rice caused by Curvularia spp. It also has an excellent control effect on other fungal rice diseases such as ADVANTAGE OF THE INVENTION According to this invention, each component of a bactericidal composition can act synergistically and can exhibit an unexpectedly remarkable control effect. Therefore, according to the bactericidal composition of the present invention, the amount of applied medicine per area can be reduced. The present invention According to the bactericidal composition of the present invention, an excellent control effect can be exerted by using a smaller amount of drug as compared with the case where the component is used alone. The effect is effective for a long time. For this reason, according to the bactericidal composition of the present invention, the number of times of treating the plant can be reduced, and the total amount of the drug used for the target plant during the cultivation period can be reduced. it can. The bactericidal composition of the present invention can exhibit excellent control effects not only when the control treatment is performed at an appropriate time for application but also when the application time is delayed. The bactericidal composition according to the present invention can control a plurality of diseases at the same time, and can reduce the risk of causing bacterial resistance. The fungicidal composition according to the present invention is expected to make a great contribution to labor saving of agriculture, protection of environment and stability of food production.

[Specific description of the invention]

Bactericidal composition

As described above, the fungicidal composition according to the present invention comprises, as active ingredients, a compound of the formula (1) or an acid addition salt thereof, and at least one compound selected from strobilurin-based insecticides. is there.

This fungicidal composition can be used for controlling plant diseases, preferably rice diseases, and more preferably paddy rice diseases. Such diseases include, for example, rice blast, sesame leaf blight, and ear blight of fungus, Curvularia spp., Discolored rice caused by Alte rnaria sp., Etc., rice scab, and sheath blight. Is mentioned. More preferably, the bactericidal composition according to the present invention is used for controlling rice blast.Here, "comprising as an active ingredient" may include a carrier according to a desired dosage form. Means, of course, that it includes the case of containing other drugs that can be used in combination.

Here, "rice" is used to include rice and upland rice. “Rice” refers to rice grown in paddy fields. Compound of formula (1)

The bactericidal composition according to the present invention comprises the compound of the formula (1) or an acid addition salt thereof. It is something.

In the formula (1), R represents a hydrogen atom, —COR ¹ , —COOR ¹ヽ —COCH ₂ 〇CH ₃ , or one CO CH ₂₀ COCH ₃ . Here, R ¹ is an alkyl group having 1 to 4 carbon atoms. In the present invention, the alkyl group may be in any of a linear, branched or cyclic form, and if necessary, one or more hydrogen atoms on the alkyl may be substituted with one or more hydrogen atoms. It may be substituted by a group (which may be the same or different). Specific examples of R ¹ include, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, and an n-butyl group. When R is a hydrogen atom in the formula (1), the compound of the formula (1) can have a structure represented by the following formula (2) which is a tautomer thereof. It is apparent to those skilled in the art that the compound of the formula (1) includes the compound of the formula (2).

In the present invention, the “acid addition salt” means a salt that can be generally used in the agricultural and horticultural fields, such as a hydrochloride, a nitrate, a sulfate, a phosphate, and an acetate.

The compound of the formula (1) may be in the form of a hydrate or a solvate, and in the present invention, such a hydrate and a solvate are also included in the compound of the formula (1). Included.

Specific examples of the compound of the formula (1) include compounds 1 to 11 of Examples described later. Method for producing compound of formula (1)

The compound of the formula (1) can be synthesized by any method suitable for forming a bond or introducing a substituent.

The compound of the formula (1) can be produced, for example, from 4-t-butyl-2-fluoroaniline, which can be synthesized by a known method, according to the following scheme.

[In the above scheme,

I is a hydrogen atom, —COR ¹ -COOR \ —COCH ₂ OCH ₃ , or one C OCH ₂ OCOCH ₃ ,

R ¹ is an alkyl group having 1 to 4 carbon atoms,

R ² is one, -OR \ —CH ₂ 〇CH ₃ , or one CH ₂₀ CO CH ₃ ].

In this scheme, first, a compound of the formula (2) is prepared (step (a)), and then, if necessary, the compound of the formula (2) is added to the compound of the formula (3) or (4) in a base By reacting in the presence or absence of a base (step (b)), a compound of the formula (1) is obtained.

The above scheme is specifically described as follows.

Step (a):

First, from 4-t-butyl-2-fluoroaline and 2-methylacetoacetate, for example, according to J. Am. Chem. Soc. 70, 2402 (1948), Tetrahedron Lett. 27, 5323 (1986) A compound of formula (2) is obtained. The compound of the formula (2) Corresponds to a compound of the formula (1) wherein R is a hydrogen atom. The 4-t-butyl-12-fluoroaniline used can be prepared, for example, by a known method described in Chem. Abs. 42, 2329 or J. Chem. Soc., Chem. Commun., 1992, 595. Obtainable.

Step (b):

Next, when a compound in which R is a hydrogen atom in the formula (1) is desired, the compound of the formula (3) or (4) is reacted in the presence or absence of a base to obtain a compound of the formula (1) ) Can be produced.

Here, usable bases include, for example, organic amines such as triethylamine and pyridine, and inorganic bases such as sodium carbonate, potassium carbonate and sodium hydride. It is desirable that the compound of the formula (3) or (4) is used in an amount of 1 to 50 equivalents, preferably 1 to 10 equivalents, based on the compound of the formula (2). The reaction in step (b) can be carried out without solvent or in an organic solvent which does not participate in the reaction, for example, in dimethylformamide or tetrahydrofuran, for example, at a temperature in the range of 0 to 140 ° C. Strobilurin fungicide

In the present invention, the stomatovirin-based bactericide may be any stoichiovirin-based bactericide as long as it is known in the art. For example, strobilurin fungicides can be found in the Pesticide Handbook, 2001 edition (2001, published by the Japan Plant Protection Association), and the Agrochemical Handbook (2001, published by the Japan Plant Protection Association, Japan) ) Are described as fungicides. A person skilled in the art can appropriately select a stoline virulin fungicide by referring to these documents.

Examples of strobilurin fungicide usable in the present invention, Azoki Shisutorobin (azoxystrobin), main Tominosuto port bin (metominostrobin), Kureso Kishimumechiru (kresoxim- methyl), trifloxystrobin (trifloxystrobin), Orisasutorobin _(or ysastrobin ), Fluoxastrobin, pyraclostrobin, and picoxystrobi n).

According to a preferred embodiment of the present invention, the stoma bilulin fungicide is selected from azoxystrobin, metominostrobin, or oryzastrobin.

According to a more preferred embodiment of the present invention, the stoma bilulin fungicide is selected from azoxystrobin or methinostrobin. Other ingredients

When the bactericidal composition according to the present invention is actually applied, a composition comprising only the above-mentioned active ingredient may be used as it is, but a suitable carrier or auxiliary agent may be further added to powder, granules, and packs. It can be prepared and used in any dosage form such as water-dispersible powder, wettable powder for granules, flowable preparation, liquid preparation, microcapsule, emulsion and the like. Thereby, the bactericidal composition according to the present invention can be suitably used for various applications depending on the purpose.

Formulation can be carried out in the same manner as in general pesticides, according to methods known in the art. Specifically, for example, the preparation can be carried out by mixing the active ingredient with a solid carrier, a solvent, a surfactant and other adjuvants, if necessary. These carriers and the like can be selected according to the purpose of improving the physical properties of the preparation, stabilizing the active ingredient, enhancing the efficacy and the like.

Solid carriers include, for example, clay, talc, calcium carbonate, diatomaceous earth, zeolite, bentonite, acid clay, activated clay, agar palgas clay, vermiculite, parlite, pumice, white carbon, titanium dioxide, water-soluble Salts, wood flour, corn cobs, knollemi husks, powdered cellulose, starch, dextrin, and sugars.

Solvents include, for example, xylene, C ₉ alkylbenzene, and the like. Aromatic solvents such as alkylbenzene, alkylnaphthylene, and high-boiling aromatic hydrocarbons; aliphatic solvents such as normal paraffin, isoparaffin, and naphthene; Solvents; machine oils such as high-boiling aliphatic hydrocarbons; alcohols such as ethanol, isopropanol, cyclohexanol, ethylene glycol, diethylene glycol, propylene glycol Polyhydric alcohols such as coal, hexylene glycol, polyethylene glycol, and propylene glycol; polyhydric alcohol derivatives such as propylene glycol ether; ketones such as cyclohexanone and aptyrolactone; fatty acid methyl esters Esters such as coconut oil fatty acid methyl ester and dibasic acid methyl ester (eg succinic acid dimethyl ester, glutamic acid dimethyl ester, adivic acid dimethyl ester); nitrogen-containing solvents such as N-alkylpyrrolidone; Fats and oils such as coconut oil, soybean oil, and rapeseed oil; and water.

Examples of the surfactant include sorbitan fatty acid ester, polyoxyethylene sorbin fatty acid ester, sucrose fatty acid ester, polyoxyethylene fatty acid ester, polyoxyethylene fatty acid ester, polyoxyethylene fatty acid diester, and polyoxyethylene fatty acid ester. Ethylene castor oil, polyoxyethylene hydrogenated castor oil, polyoxyethylene alkyl ether, polyoxyethylene alkylphenyl ether, polyoxyethylene dialkylphenyl ether, polyoxyethylene alkyl ether / formalin Condensate, polyoxyethylene / polyoxypropylene propylene polymer, alkylpolyxylene / polypropylene propylene block polymer, alkylphenylpolystyrene / polyoxypropylene Pyrene block polymer ether, polyoxyethylene alkylamine, polyoxyethylene fatty acid amide, polyoxyethylene bisphenyl ether, polyoxethylene benzyl phenyl ether, polyoxyethylene styryl ether, poly Nonionic surfactants such as oxyethylene ether type silicon, ester type silicon, fluorine type surfactant, alkyl sulfate, polyoxyethylene alkyl ether sulfate, polyoxyethylene alkyl phenyl ether sulfate, polyoxy Ethylene benzyl phenyl ether sulfate, polyoxyethylene / polyoxypropylene block polymer sulfate, paraffin sulfonates, AOS, dialkyl sulfosuccinates, alk Benzenesulfonates, naphthalenesulfonates, naphthalenesulfonate / formalin condensates, alkyldiphenylterdisulfonates, ligninsulfonates, polyoxyethylene alkylphenylates Sulfonates, polyoxyethylene alkyl ether sulfosuccinic acid half esters, fatty acid salts, N-methyl-fatty acid sarcosinates, resin salts, polyoxyethylene alkyl ether phosphates, polyoxyethylene alkyl ether phosphates , Polyoxyethylene benzylated phenyl ether phosphates, polyoxyethylene nopolyoxypropylene block polymer phosphates, lecithins, alkyl phosphates, alkyltrimethylammonium chlorides, methyl / polyoxy Ethylene alkyl ammonium chlorides, alkyl N-methyl-pyridinium bromides, alkyl methylated ammonium chlorides, alkyl pentyne methyl propylene diamine Kurorai de, alkyl dimethyl benzalkonium Niu skeleton Rye earths Benzeto Niumukurorai earth, dialkyl aminoethyl downy evening ynes, and alkyl di like methylbenzyl downy evening ynes.

Adjuvants include, for example, isopropyl phosphate, carboxymethyl cellulose, PVA, sodium tripolyphosphate, sodium hexanoxate, xanthan gum, guar gum, carboxymethylcellulose, sodium benzoate, sorbin Potassium acid, parahydroxybenzoic acid ester, 1,2-benzodiazoline-3-one, ethylene glycol, diethylene glycol, propylene glycol, polyvinylprovidone, urea, hexamethylenetetramine, antioxidant, ultraviolet ray absorbent, Zeolite, quicklime, magnesium oxide, hydrophobic high-boiling solvents, polyacrylic acid soda, alginic acid, kraft lignin, copolymers of methacrylic acid and vinylpropidone, glycerin, sorbitol, and water-swellable polymers Compound Things.

The above carriers, surfactants, dispersants, and auxiliaries may be used in combination of two or more selected from within each group and between groups. In the bactericidal composition according to the present invention, the compound of the formula (1) or an acid addition salt thereof and at least one compound selected from strobilurin-based insecticides are combined in a total amount (active ingredient amount) of the bactericidal composition. It is sufficient that the content is 0.1 to 90 parts by weight, preferably 1 to 70 parts by weight, in 100 parts by weight of the acidic composition. The amount of the active ingredient can be appropriately selected in consideration of the formulation of the bactericidal composition, the application method, the use environment, and other conditions. For example, when the germicidal composition is in the form of a hydrating agent, it is 5 to 50% by weight, preferably 10 to 30% by weight, and when the germicidal composition is in the form of a powder, it is 0 to 50% by weight. It is from 5 to 5.0% by weight, preferably from 1.0 to 2.0% by weight.

In the fungicidal composition according to the present invention, the compounding ratio of the compound of the formula (1) or an acid addition salt thereof to at least one compound selected from strobilurin-based insecticides is 2:50 to 50: 2. by weight, preferably from 1: 1 0~: L 0: when using the fungicidal composition according to _c present invention is one of the range, it may be directly used, as required water It can be diluted with a diluent such as, and applied to the area to be treated, such as spraying, mixing, water application, and immersion. Examples of such treatment include, for example, application to a plant itself (foliage application), application to a nursery box (application of a nursery box), application to soil (soil admixture or lateral application), Application to water (surface application or Honda application) or application to seed (seed treatment).

According to another aspect of the present invention, there is provided a method for controlling rice disease, comprising applying an effective amount of the bactericidal composition according to the present invention to a region to be treated. Here, the “region to be treated” refers to a region that needs to be treated using the bactericidal composition according to the present invention for controlling rice diseases. , Nursery boxes, soil, paddy water, or seeds. Preferably, the area to be treated is rice plants, soil, or paddy water.

The amount of the bactericidal composition according to the present invention can be appropriately changed according to the use environment, the growth state of the target plant, the mixing ratio of the active ingredients, the formulation, the application time, the application method, and the type of the disease to be controlled. Usually, the amount is such that the amount of the active ingredient per 10 ares is 1 to 1,500 g, preferably 10 to 150 g. For example, when the fungicidal composition is applied to a rice plant, the amount of the active ingredient used is 5 to 500 g per 10 ares, preferably 10 to 100 g. C The bactericidal composition according to the present invention may be used in a mixture with other fungicides, insecticides, acaricides, herbicides, plant growth regulators, fertilizers and the like.

The bactericidal composition according to the present invention is prepared and formulated in advance as described above. It is usually used, but the compound of the formula (1) or an acid addition salt thereof, which is an active ingredient in the composition, and at least one compound selected from stomatal bilulin insecticides are used. May be prepared separately, and these may be mixed in situ when used.

Thus, according to another aspect of the present invention there is provided a combination comprising a compound of formula (1) or an acid addition salt thereof, and at least one compound selected from strobilurin insecticides.

According to another preferred embodiment of the present invention, in the combination, the compound of formula (1) or an acid addition salt thereof is provided as a first composition comprising the compound as an active ingredient, and a strobilurin-based compound. At least one compound selected from pesticides is provided as a second composition comprising it as an active ingredient. In this case, the first composition and the second composition can be in any dosage form by using a suitable carrier or auxiliary agent in combination, as in the case of the above-mentioned bactericidal composition. The combination may be provided in the form of a drug set.

According to another aspect of the present invention, there is provided the use of the above-mentioned combination for producing an agent for controlling rice disease. Here, the “paddy rice disease controlling agent” comprises the bactericidal composition according to the present invention.

According to yet another aspect of the present invention, there is provided a method for controlling a rice disease, comprising: a compound of the formula (1) or an acid addition salt thereof, and at least one compound selected from a stomatal virulin insecticide. And simultaneously or separately applying to the area to be treated.

In this method, the "simultaneous" application involves applying to the area to be treated a compound of formula (1) or an acid addition salt thereof and at least one compound selected from strobilurin pesticides. Mixing before applying and applying the mixture is also included. "Separate" application includes applying the compound of formula (1) or an acid addition salt thereof prior to the other component without premixing them, and the compound of formula (1) or the acid thereof. It involves applying the addition salt after the other component.

According to yet another preferred embodiment of the present invention, (A) a first composition comprising a compound of the formula (1) or an acid addition salt thereof as an active ingredient;

(B) a second composition comprising, as an active ingredient, at least one compound selected from stomatovirin-based insecticides;

Is applied to an area to be treated, and a method for controlling rice diseases is provided.

[Example]

Hereinafter, the present invention will be described in detail with reference to the following examples, but the present invention is not limited thereto. Preparation of the compound of formula (1)

Compounds of the formula (1) having the substituents as shown in Table 1 below (compounds 1 to 11) were produced.

Substituent

RR ¹

Compound 1 H

Compound 2 -COR ¹ -CHa

Compound 3-COR ¹ -C 2 H 5

Compound 4 -COR ¹ ― C 3 H 7

Compound 5-COR ¹ ― C 4 H 9

Compound 6 -COOR ¹ CH ₃

Compound 7 -COOR ¹ ― C 2 H 5

Compound 8 -COOR ¹ C 3 H 7

Compound 9 -COOR ¹ ― C 4 H 9

Compound 10 -COCHzOCHs

Compound 11-CO CH ₂ 0 CO CH ₃ The production of Compounds 1 to 11 was specifically performed according to the following procedure. Production of 4-t-butyl 2-fluoroaniline

SELECTFLUOR (manufactured by Aldrich Chemical Company Inc) (200 ml of acetonitrile) (1-chloro monomethyl 4-fluoro-1,4-diazodiabicyclo [2,2,2] octane-bis-tetrafluoroborate) (15 g) was heated at 70 ° C for 30 minutes to dissolve. The resulting reaction solution was cooled to 60 ° C., and thereto was added 4-t-butyl acetate (5.7 g). The mixture was stirred at 100 ° C. for 1 hour and allowed to cool. Then, the reaction solution was added to water (200 ml), and extracted with ethyl acetate (100 ml, twice). The ethyl acetate layer was washed with saturated saline, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained crude product was purified using silica gel chromatography (Co-gel C-200 (manufactured by Wako Pure Chemical Industries, Ltd.), elution solvent n-hexane monoethyl acetate (10: 1)). There was obtained t-butyl-2-fluorescetanilide (3.06 g). This 4-t-butyl-2-fluoroacetanilide (3.67 g) was added to a mixture of ethanol (30 ml) and concentrated hydrochloric acid (15 ml), and the mixture was stirred at 95 ° C for 2 hours. The reaction solution was allowed to cool, poured into water, neutralized with a saturated aqueous solution of sodium hydrogen carbonate, and extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated saline, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to give 4-t-butyl-2-fluoroaniline (3. 49 g) were obtained. The ¹ H-NMR data of this compound in the form of a magnetic opening are shown below.

d (m): 7.01 (1H, dd), 6.95 (1H, dd), 6.73 (1Η, m), 1.28 (9Η, s) Compound 1: 2, 3— Dimethyl-6-t-butyl-8-fluoro-4-hydroxyquinoline

4-t-Butyl-2-fluoroaniline (4.79 g) and 2-methylethylacetoacetate (4.96 g) obtained according to the above process were combined with trifluoroborolone (0.3 ml). In toluene (60 ml) in the presence of After refluxing for an hour, a reaction solution was obtained. The obtained reaction solution was washed with a saturated aqueous solution of sodium hydrogen carbonate and a saturated saline solution, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained reaction product was refluxed in diphenyl ether (80 ml) for 1 hour, allowed to cool, and the precipitated product was collected by filtration under reduced pressure to give 2,3-dimethyl-6-t-butyl. One 8-fluoro-4-hydroxyquinoline (compound 1) (1.66 g) was obtained. The ¹ H-NMR data of this compound in heavy DMSO (dimethyl sulfoxide) is shown below.

d (ppm): 11.27 (lH, br.s), 7.83 (1H, s), 7.59 (1H, br.d), 2.41 (3H, s), 1.96 ( 3H, s), 1.31 (9H, s) compound 2: 2, 3-dimethyl-6-t-butyl-8-fluoro-4-acetylquinoline

Compound 1 (50 mg) was stirred in acetic anhydride (3 ml) at 120 ° C. for 3 hours to obtain a reaction solution. Acetic anhydride was distilled off from the obtained reaction solution under reduced pressure.The obtained residue was dissolved in ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution and saturated saline, and then dried over anhydrous sodium sulfate. Thereafter, the solvent was distilled off under reduced pressure. The obtained crude product was purified by silica gel chromatography (Cogel C-200, elution solvent n-hexane-ethyl acetate (5: 1)) to give 2,3-dimethyl-6_t-butyl-1. —Fluoro-4-acetylquinoline (I-Danigo Compound 2) (35.7 mg) was obtained. A ¹ H-NMR spectrum of this compound in a double-mouthed form is shown below.

d (m): 7.43 (1H, dd), 7.37 (1H, d), 2.78 (3H, s), 2.51 (3H, s), 2.26 (3H , s), 1.38 (9 H, s) compound 3 ··· 2,3-dimethyl-1-6-t-butyl-8-fluoro-4-propionylquinoline

Suspend 60% sodium hydride (20mg) in tetrahydrofuran (3ml) Then, Compound 1 (124 mg) was added thereto under ice cooling, and the mixture was stirred for 30 minutes. Propionyl chloride (200〃1) was further added thereto, and the mixture was stirred for 3 hours. The obtained reaction solution was poured into ice water, extracted with ethyl acetate, the ethyl acetate layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and a saturated saline solution, and then dried over anhydrous sodium sulfate. The lower solvent was distilled off. The obtained crude product was purified by silica gel chromatography (ヮ co-gel C-200, elution solvent n-hexane-ethyl acetate (3: 1)) to give 2,3-dimethyl-6-t —Butyl-8-fluoro-4--4-propionylquinoline (21 mg) (Compound 3) was obtained. A ¹ H-NMR spectrum of this compound in a form of chloroform is shown below.

d (ppm): 7.42 (1H, dd), 7.36 (1H, d), 2.81 (2H, q), 2.75 (3H, s), 2.2 5 (3 H, s), 1.43 (3H, t), 1.37 (9 H, s) Compound 42,3-Dimethyl 6-t-butyl-8-fluoro-4-butyrylquinoline

60% sodium hydride (20 mg) was suspended in tetrahydrofuran (3 ml), to which Compound 1 (124 mg) was added under ice-cooling, followed by stirring for 30 minutes. To this was further added petryl chloride (200 zl), and the mixture was stirred for 3 hours. The obtained reaction solution was poured into ice water, extracted with ethyl acetate, and the ethyl acetate layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated saline, then dried over anhydrous sodium sulfate, and then dried under reduced pressure. The solvent was distilled off. The obtained crude product was purified by silica gel chromatography (ヮ -gel C-200, elution solvent n-hexane monoethyl acetate (3: 1)) to give 2,3-dimethyl-6-t- Butyl-8-fluoro-4-butyrylquinoline (Compound 4) (64 mg) was obtained. The ¹ H-NMR data of this compound in a double-mouthed form are shown below.

ά (pm): 7.43 (1H, dd), 737 (1H, d), 276 (2H, t), 2.75 (3H, s), 225 (3H, s), 1 94 (2H, m), 1.37 (9H, s), 1 15 (3H, t) Compound 5: 2,3-dimethyl-6-t-butyl-8-fluoro-4-valerylquinoline

60% sodium hydride (20 mg) was suspended in tetrahydrofuran (3 ml), to which Compound 1 (124 mg) was added under ice-cooling, followed by stirring for 30 minutes. Valeryl chloride (200/1) was further added thereto, and the mixture was stirred for 3 hours. The obtained reaction solution was poured into ice water, extracted with ethyl acetate, and the ethyl acetate layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated saline, then dried over anhydrous sodium sulfate, and then dried under reduced pressure. The solvent was distilled off. The obtained crude product was purified by silica gel chromatography (Co-gel C-200, elution solvent n-hexane-ethyl acetate (3:

1))) to give 2,3-dimethyl-6-t-butyl-8-fluoro-4-valerylquinoline (Compound 5) (12 Omg). The ¹ H-NMR spectrum of this compound in deuterated chloroform is shown below.

δ (p pm): 7.42 (1H, dd), 7.37 (1H, d), 2.

78 (2H, t), 2.75 (3 H, s), 2.25 (3 H, s), 1.

89 (2H, m), 1.56 (2H, m), 1.37 (9H, s), 1.

03 (3H, t) compound 6: 2,3-dimethyl-6_t-butyl-1-8-fluoro-4-methoxycarbonylquinoline

60% sodium hydride (20 mg) was suspended in tetrahydrofuran (3 ml), to which Compound 1 (124 mg) was added under ice-cooling, followed by stirring for 30 minutes. Methyl chloroformate (200〃1) was further added thereto, and the mixture was stirred for 3 hours. The obtained reaction solution was poured into ice water, extracted with ethyl acetate, and the ethyl acetate layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated saline, dried over anhydrous sodium sulfate, and then dried under reduced pressure. The solvent was distilled off. The crude product obtained was purified by silica gel chromatography (ヮ -gel C-200, elution solvent n-hexane monoethyl acetate (3: 1)) to give 2,3-dimethyl-6-t- Butyl-8-fluoro-4-methoxycarbonylquinoline (Compound 6) (l O Omg) was obtained. The ¹ H-NMR spectrum of this compound in double-mouthed form is shown below. d (ppm): 7.45 (1H, br.s), 7.43 (1H, dd),

4.00 (3H, s), 2.76 (3H, s), 2.31 (3H, s), 1.38 (9H, s) Compound 7: 2,3-Dimethyl-1-6-t-butyl-8 Fluoro-4-ethoxycarbonylquinoline

60% sodium hydride (6 Omg) was suspended in tetrahydrofuran (10 ml), to which Compound 1 (20 Omg) was added under ice-cooling, followed by stirring for 30 minutes. Ethyl chloroformate (200〃1) was further added thereto, and the mixture was stirred for 3 hours. The obtained reaction solution was poured into ice water, extracted with ethyl acetate, and the ethyl acetate layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated saline, and then dried over anhydrous sodium sulfate. The lower solvent was distilled off. The obtained crude product was purified by silica gel chromatography (ヮ -gel C_200, elution solvent n-hexane-ethyl acetate (3: 1)) to give 2,3-dimethyl-6-t-butyl. —8-Fluoro-4-ethoxyethoxycarbonylquinoline (Compound 7) (22 Omg) was obtained.

A ¹ H-NMR spectrum of this compound in a double-mouthed form is shown below.

δ (ppm): 7.45 (1H, br. s), 7.43 (1H, dd), 4.40 (2H, q, J = 6.7 Hz), 2.32 (3H, s,) , 2.04 (3H, s), 1.44 (3H, t), 1.38 (9 H, s) Compound 8: 2,3-dimethyl-6-t_butyl-18-fluoro-4-1-normal propoxycarbo Nilquinoline

60% sodium hydride (2 Omg) was suspended in tetrahydrofuran (3 ml), to which Compound 1 (124 mg) was added under ice-cooling, followed by stirring for 30 minutes. Normal propyl chloroformate (200/1) was further added thereto, and the mixture was stirred for 3 hours.c The reaction solution obtained was poured into ice water, extracted with ethyl acetate, and the ethyl acetate layer was saturated with an aqueous sodium hydrogen carbonate solution. After washing with a saline solution and then drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The obtained crude product is subjected to silica gel chromatography (ヮ -gel C-200, elution solvent n-hexane monoacetate). (3: 1)) to give 2,3-dimethyl-6-t-butyl-8-fluoro-1-N-propoxycarbonylcarbonylquinoline (Compound 8) (96 mg). A ¹ H-NMR spectrum of this compound in a double-mouthed form is shown below. δ (ppm): 7.45 (1H, br.s), 7.43 (1H, dd), 4.35 (2H, t, J = 6.7 Hz), 2.75 (3H, s), 2 3 l (3H, s), 1.82 (2 H, m), 1.38 (9H, s), 1.04 (3 H, t) Compound 9: 2, 3-dimethyl-6_t— Butyl-8-fluoro-4-normal butoxycarbonylquinoline

60% sodium hydride (60 mg) was suspended in tetrahydrofuran (10 ml), and compound 1 (200 mg) was added thereto under ice cooling, followed by stirring for 30 minutes. Normal butyl chloroformate (200/1) was further added thereto, and the mixture was stirred for 3 hours. The resulting reaction solution was poured into ice water, extracted with ethyl acetate, and the ethyl acetate layer was washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated sodium chloride solution. After washing with water and drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel chromatography (ヮ -gel C-200, elution solvent n-hexane monoacetate (3: 1)) to give 2,3-dimethyl-6-t —Butyl-8-fluoro-4-N-butoxycarboxyquinoline (compound 9) (142 mg) was obtained. A ¹ H-NMR spectrum of this compound in a double-mouthed form is shown below.

5- (ppm): 7.45 (1H, d), 7.43 (1H, dd), 4.35 (2H, t), 2.75 (3H, s), 2.32 (3H, s) ), 1.77 (2 H, m), 1.48 (2 H, m), 1.38 (9H, s), 0.99 (3 H, t) Compound 10: 2,3-Dimethyl_6_t— Butyl _8-fluoro-4-methoxyacetylquinoline

60% sodium hydride (165 mg) was suspended in tetrahydrofuran (10 ml), and Compound 1 (680 mg) was added thereto under ice cooling, followed by stirring for 30 minutes. Methoxyacetyl chloride (200/1) was further added thereto, and the mixture was stirred for 3 hours. The obtained reaction solution was poured into ice water, extracted with ethyl acetate, the ethyl acetate layer was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated saline, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel chromatography (ヮ -gel C-200, elution solvent n-hexane monoacetate (3: 1)) to give 2,3-dimethyl-6- There was obtained 390 mg of t-butyl-8-fluoro-4-methoxymethoxyacetylquinoline (Compound 10). The ¹ H-NMR data of this compound in a double-mouthed form are shown below.

δ (ppm): 7.42 (1H, dd), 7.35 (1H, d), 4.51 (2H, s), 3.62 (3H, s), 2.75 (3H , S), 2.26 (3H, s), 1.37 (9H, s) Compound 11 1: 2,3-dimethyl-6-t-butyl-8-fluoro-4-acetoxyacetylquinoline

60% Sodium hydride (44 mg) was suspended in tetrahydrofuran (10 ml), to which Compound 1 (200 mg) was added under ice cooling, followed by stirring for 30 minutes. Acetoxyacetyl chloride (100〃1) was further added thereto, and the mixture was stirred for 3 hours. The obtained reaction solution was poured into ice water, extracted with ethyl acetate, the ethyl acetate layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated saline, and then dried over anhydrous sodium sulfate. The lower solvent was distilled off. The resulting crude product was purified by silica gel chromatography (ヮ -gel C-200, elution solvent n-hexane monoacetate (3: 1)) to give 2,3-dimethyl-6-t- 1-Phenyl-1-fluoro-4-acetoxyacetylquinoline (Compound 11) (140 mg) was obtained. C The ¹ H—N MR data of this compound in double-mouthed form are shown below.

ό- (ppm): 7.43 (1H, dd), 7.42 (1H, br.s),

5.02 (2H, s), 2.75 (3H, s), 2.27 (3Η, s),

2.23 (3 H, s), 1.40 (9 H, s) Formulation example

Formulation example wettable powder

The following components were uniformly ground to obtain a wettable powder.

Compound 220 parts by weight Azoxystrobin 20 parts by weight Diatomaceous earth 28 parts by weight White carbon (trade name) (manufactured by Shionogi & Co., Ltd.)

3 Polyoxetylene lauryl ether 2 Calcium ligninsulfonate 7 Formulation example 2: wettable powder

The following components were uniformly ground to obtain a wettable powder ₍

Compound 2 15 azoxystrobin 5 parts by weight diatomaceous earth '47 parts by weight Kureichi 10 parts by weight white carbon (trade name) (manufactured by Shionogi & Co., Ltd.)

10 parts by weight Polyoxyethylene lauryl ether 8 parts by weight Calcium ligninsulfonate 5 parts by weight Formulation example 3: wettable powder

The following components were uniformly ground to obtain a wettable powder <

Compound 2 20 parts by weight Azoxystrobin 10 parts by weight Diatomaceous earth 42 parts by weight Kureichi 5 parts by weight White carbon (trade name) (manufactured by Shionogi & Co., Ltd.) 0 parts by weight Polyoxyethylene lauryl ether 8 parts by weight Calcium ligninsulfonate 5 parts by weight Formulation Example 4: Wetting agent

The following components were uniformly ground to obtain a wettable powder <

Compound 220 parts by weight Metominostrobin 20 parts by weight Diatomaceous earth 37 parts by weight White Rikibon (brand name) (manufactured by Shionogi & Co., Ltd.)

10 parts by weight Polyoxyethylene lauryl ether 8 parts by weight Calcium ligninsulfonate 5 parts by weight Formulation example 5: wettable powder

The following components were uniformly ground to obtain a wettable powder.

Compound 2 15 parts by weight Metominostrobin 5 Diatomaceous earth 47 parts by weight Kureichi 10 parts by weight White carbon (trade name) (manufactured by Shionogi & Co., Ltd.)

10 parts by weight Polyoxyethylene lauryl ether 8 Calcium ligninsulfonate 5 Formulation example 6: wettable powder

The following components were uniformly ground to obtain a wettable powder <

Compound 220 parts by weight Metominostrobin 10 parts by weight Diatomaceous earth 42 parts by weight Clay 5 parts by weight White power bon (brand name) (manufactured by Shionogi & Co., Ltd.)

'10 parts by weight Polyoxyethylene lauryl ether 8 parts by weight Calcium ligninsulfonate 5 parts by weight Formulation example 7: Powder

The following components were uniformly ground to obtain a powder.

Compound 2 1.2 Azoxystrobin 0 · 5 Klei 97.1 Calcium carbonate 0.5 White carbon (trade name) (manufactured by Shionogi & Co., Ltd.)

0.2 parts by weight Doreless A (trade name) (manufactured by Sankyo Co., Ltd.) 0.5 parts by weight Formulation Example 8: Powder

The following components were uniformly ground to obtain a powder.

Compound 2 1 part by weight azoxystrobin 0.5 clay 97.1 calcium bicarbonate 0.5 part:] part White Ribon (brand name) (manufactured by Shionogi & Co., Ltd.)

0. Double jt part Doreless A (trade name) (manufactured by Sankyo Co., Ltd.) 0.5 Double jt part Formulation Example 9: Powder

The following components were uniformly ground to obtain a powder.

Compound 2 2

Meminostrobin 0 5

Clay 9 7

0 5 parts by weight of calcium carbonate White Rikibon (brand name) (manufactured by Shionogi & Co., Ltd.)

0.2 parts by weight Doreless A (trade name) (manufactured by Sankyo Co., Ltd.) 0.5 parts by weight Formulation Example 10 0: Powder

The following components were uniformly ground to obtain a powder.

Compound 21 1 part by weight Methominostrobin 0.5 part by weight Clay 97.1 parts by weight Calcium carbonate 0.5 part by weight White carbon (trade name) (manufactured by Shionogi & Co., Ltd.)

0.4 parts by weight Drilles A (trade name) (manufactured by Sankyo Co., Ltd.) 0.5 parts by weight Evaluation test

Test A: Control effect of rice blast by spraying before infestation

Culture soil was placed in a plastic bait (approx. 3 cm x 50 cm), and seeded rice seed (variety: Koshihikari) was sowed and densely planted. The rice was cultivated in a glass greenhouse at 25 ° C in the daytime and 20 ° C at night for about 2 weeks, and when it grew at the 3-4 leaf stage, the rice blast fungus (race 0 37 ) Was inoculated and diseased leaves were placed on the densely planted rice. This was placed in a humid condition for 24 hours to inoculate the bacteria. The rice was returned to the glass greenhouse again, and after 7 to 8 days, the lesion was confirmed, and the first spraying of the drug was performed. The reagent solution is 1 The concentration was adjusted to a predetermined concentration using 0% acetone water (a 500,000-fold solution of Neoesterin (trade name) (manufactured by Kumiai Chemical Industry Co., Ltd.) as a spreading agent), and spray gun was applied. And sprayed 15 ml per vat. When the second drug application was performed, the same procedure was applied to the first drug application and the second drug application 6 to 7 days later. After spraying, the rice was maintained in a glass greenhouse and kept humid for 24 hours at intervals of 1 to 2 days to promote disease and spread.

Ten days after the final spraying of the drug, the lesion area on the leaf blade of the lowermost leaf was observed for 40 strains per vat, and the lesion area ratio of the treated plot was determined. From the obtained results and the results obtained in the untreated plot, the control value for each test drug was calculated according to the following formula.

Control value = [1-(Lesion area ratio in treated plot / Lesion area rate in untreated plot)] X 100 The preventive and residual effects of the test drug are determined at the time after the prescribed number of days after drug treatment Thus, it can be determined whether or not the lesion area ratio increases. Therefore, the preventive effect and residual effect were determined based on whether or not the finally obtained control value was high.

The test was performed for each group, with the drugs listed in Tables A1 to A3 below as one group. The spraying of the drug was performed once or twice.

The results were as shown in Tables A1 to A3. Table A Twice spray test Drug concentration (ppm) Lesion area rate Control value No treatment 35.9

Compound 280.5.0 86 azoxystrobin 800.3.092 Compound 2 + azoxystrobin 40 + 400.49 Table A Double spray test Drug concentration (ppm) Lesion area rate Control value No treatment 35.8

Compound 2 80 17.9 50 Azoxystrobin 80 20.0 44 Compound 2 + Azoxystrobin 40 + 40 10.67

Table A3: Single spray test Drug concentration (ppm) Lesion area rate Control value No treatment 40. 6

Compound 2 80 15.1 63 Compound 3 80 21.4 47 Compound 11 80 18.3 55 Azoxystrobin 80 14.1 65 Methominostrobin 80 20.9 49 Compound 2 + Azoxystrobin 40 + 40 4.190 compound 3 + azoxystrobin 40 + 40 6.983 compound 11 + azoxystrobin 40 + 40 5.4.87 compound 2 + methinostrobin 40 + 40 10.973 compound 3 + Metominostrobin 40 + 40 13.66 66 Compound 11 + Metominostrobin 40 + 40 14.5 64 Test B: Rice Blast Control Effect by Spraying after Spread (Delaying Test)

Culture soil was placed in a plastic vat (about 30 cm x 50 cm), seeded rice seeds (variety: Koshihikari) that had been germinated, and densely planted were used. The rice was cultivated in a glass greenhouse at 25 ° C in the daytime and 20 ° C at night for about 2 weeks. The diseased leaves that had been diseased were placed on the densely planted rice. This was placed in a humid condition for 24 hours to inoculate the bacteria. The rice was placed again in a glass greenhouse, and lesions were confirmed 7 to 8 days later. After that, they were placed again in a humid condition for 24 hours to promote secondary transmission, and to spread rice blast in the knots. About three or four days after the spread of the disease, the first drug spraying was performed after the tiny secondary lesions could be confirmed.

Conditions other than the above, such as the reagent solution conditions, spraying method, spraying interval, disease control method after the start of spraying, calculation of lesion area ratio, and calculation of control value were performed in the same manner as in Test A. . Also, in the case of performing the second drug spraying, the drug spraying interval was the same as in Test A described above.

The test was performed for each group, with the drugs listed in Tables B1 to B listed below as one group.

The results were as shown in Tables B1 to B. Table B 1 Double spray test Drug concentration (ppm) Lesion area rate Control value No treatment 81.5

Compound 2 80 27.6 66 azoxystrobin 80 21. 4 74 Compound 2 + azoxystrobin 40 + 40 12.2 85 Table B 2 Single spray test Drug Concentration (ppm) Lesion area rate Control value No treatment 74.5

Compound 2 o υ 0 O Azoki IT-insi: Trobin ο U (Compound 2 + Azoxystrobin 4 U 10 Ω Q

4 U 7

Table B 3: Single spray test Drug concentration (ppm) Lesion area rate Control value No treatment 30.0

Compound 2 80 16.6 45 Azoxynitropin 80 10. 9 64 Compound 2 + Azoxystrobin 40 + 40 4.85 85

Table B4: Single spray test

, Kakuhachi / Drug concentration (ppm) '-Lesion area rate Control value No treatment 73, 3

Compound 2 80 19, 0 74 Compound 3 80 31.3 57 Compound 1 1 80 27.8 86 62 Azoxystrobin 80 19.0.74 Metominostrobin 80 27.4 4 63 Compound 2 + Azoxystrobin 40 + 40 14.4 80 Compound 3 + Azoxystrobin 40 + 40 13. 1 82 Compound 11 1 + Azoxystrobin 40 + 40 12.583 Compound 2 + Metominostrobin 40 + 40 11, 584 Compound 3 + Metominostrobin 40 + 40 15, 379 Compound 11 + Metominostrobin 40 + 40 15.5 79

Claims

Scope of request The following formula (1)

[Wherein, R is a hydrogen atom, one COIT-COOR ¹ (where R ¹ is an alkyl group having from L to 4 carbon atoms), one COCH ₂ 〇CH ₃ or one COCH ₂ OCOCH ₃ ]

Or a compound or an acid addition salt thereof,

At least one compound selected from stork bilulin insecticides

A bactericidal composition comprising, as an active ingredient.

2. The bactericidal composition according to claim 1, wherein the stomatovirin insecticide is selected from azoxystrobin or methinomin stoichiometric bottle.

3. The fungicidal composition _c according to claim 1 or 2, which is used for controlling rice diseases.

4. The fungicidal composition _c according to claim 1 or 2 which is used for controlling rice disease.

5. The bactericidal composition according to claim 3, wherein the disease is rice blast.

6. The following equation (1):

Wherein, I or hydrogen atom, - COR ¹ -COOR ¹ (wherein R ¹ is an alkyl group having 1 to 4 carbon atoms), _ (0011 ₂ 〇 11 ₃ or _〇_0_Rei_11 ₂ 0_Rei_rei (11 ₃ )

Or a compound or an acid addition salt thereof,

At least one compound selected from strobilurin insecticides;

A combination comprising:

7. Use of the bactericidal composition according to claim 1 or 2 for producing an agent for controlling rice disease.

8. Use of the combination according to claim 6 for producing a rice disease control agent ο

9. Use according to claims 7 and 8, wherein the disease is rice blast.

10. A method for controlling rice diseases, comprising applying an effective amount of the bactericidal composition according to claim 1 to an area to be treated.

11. A method for controlling rice diseases,

The following formula (1):

[Wherein R is a hydrogen atom, one COR ¹ -COOR ¹ (where R ¹ is an alkyl group having 1 to 4 carbon atoms), one COCH ₂ OCH ₃ or one COCH ₂ OCOCH ₃ ]

Or a compound or an acid addition salt thereof,

At least one compound selected from strobilurin insecticides;

Applying, simultaneously or separately, to the area to be treated.

12. The method c according to claim 11, wherein each component is applied to an area to be processed simultaneously.

13. The method according to any one of claims 10 to 12, wherein the strobilurin insecticide is selected from aV xoxystrobin or metminostrobin.

14. The method according to any one of claims 10 to 13, wherein the disease is a rice disease.

15. The method according to any one of claims 10 to 14, wherein the disease is rice blast.

16. The method according to any one of claims 0 to 15, wherein the area to be treated is a rice plant, soil, or paddy water.