WO2003075662A1 - Fungicidal composition for control of rice plant disease - Google Patents

Abstract

A fungicidal composition comprising as an effective ingredient at least one compound selected from the group consisting of compounds of the following formula (1) [wherein R represents a hydrogen atom, -COR1, -COOR1 (wherein R1 is a C1-C4 alkyl), -COCH2OCH3 or -COCH2OCOCH3] or acid adducts thereof, compounds having a melanin biosynthesis inhibiting activity and Kasugamycin. This fungicidal composition is useful for control of rice plant blast.

Description

 Fungicidal composition for controlling rice disease

[Background of the invention]

Field of the invention

 The present invention relates to a bactericidal composition having an excellent rice disease controlling effect,

The present invention relates to a fungicidal composition having an effect of controlling rice blast.

Related technology

 Blast disease is one of the plant diseases. Blast is a type of filamentous fungus

It is a disease of plants caused by parasitism of Pyricularia spp. Above all, rice blast (Pyricularia oryzae) may occur during abnormal weather such as low temperature or heavy rain in summer, and is one of the important diseases in rice cultivation. WO 01/92231 (International Publication Date: 2001/12/06) discloses a compound represented by the following formula (1) or an acid addition salt thereof having excellent bactericidal activity:

[Wherein, R is a hydrogen atom, 110〇, -COOR ¹ (here, an alkyl group having 1 to 4 carbon atoms), —COCH ₂ OCH ₃ or —COCH ₂ OCOCH ₃ ]. It also describes the physicochemical properties of this compound and its control effect on rice blast. Furthermore, here, this compound has not only an excellent therapeutic effect on rice blast, but also an excellent residual and preventive effect, which is the same as the therapeutic effect of existing rice blast control agents. It also states that they are different. Compounds that have a controlling effect on several rice diseases including rice blast include fusalide (4,5,6,7-tetrachlorophthalide) and tricyclazole (5-methyl-1). , 2, 4-triazolo [3, 4-b] ben, zothiazole), diclosimette ((: RS)-2-cyano N-[(R)-1-(2, 4 dichloro phenyl) ethyl)-3, Compounds having a melanin biosynthesis inhibitory action, such as 3-dimethylbutyramide) and phenoxanyl (N- (2,3-diclo-4-hydroxyphenyl) -1-methylcyclohexanecarboxamide); and Kasugamycin has been reported and its mechanism of action has been reported. These are described, for example, in the abstracts of the 1999 Annual Meeting of the Japanese Society of Plant Pathology (1992, published by the Japanese Society of Plant Pathology), in the abstracts of the 2001 Annual Meeting of the Japanese Society of Plant Pathology (2000) 1 year, published by the Japanese Society for Plant Pathology), and the Agrochemical Handbook, 2001 edition (2010, published by the Japan Plant Protection Association). Japanese Patent Publication No. 63-503321, filed in Japan, discloses a pyrimidine derivative having a therapeutic effect on rice blast and a compound having a melanin biosynthesis inhibitory effect having a preventive effect on rice blast. An agricultural fungicidal composition comprising: It is described therein that the bactericidal composition has both a preventive effect and a therapeutic effect, and that these components exhibit a synergistic effect.

 According to the Japanese Patent Application No. Hei 2-6728 and Japanese Patent Application Laid-Open No. Hei 6-27915, the control effect of kasugamycin on rice blast is strongly therapeutic and sprayed prophylactically. In this case, the residual effect and rain resistance are not always sufficient. Therefore, a mixed composition of kasugamycin in consideration of this problem is disclosed. The purpose of these mixed compositions is to obtain a higher control effect due to a synergistic effect with other components, while having a lower concentration than when kasugamycin is used alone.

However, recently, problems such as emergence of resistant bacteria to conventional drugs have arisen. In addition, depending on climatic conditions such as cold damage and long rainy season, and cultivation conditions such as poor management of nursery and fertilizer application, rice blast can occur even when such a pesticide is used. In some cases, it was found. For this reason, the development of a control agent with even better control effect is desired. Recently, farmers have been part-time jobs and farmers are aging more and more. Need technology to mitigate,

[Overview of the invention]

 The present inventors have now comprised a compound of the following formula (1) (a 2,3-dimethyl-6-t-butyl 8-fluoro-4-quinolinol derivative), a compound having an inhibitory action on melanin biosynthesis, and kasugamycin. A mixed composition comprising one or more compounds selected from the group not only does not impair the activity of each component, but also exhibits a synergistic effect and exhibits an excellent rice blast control effect. I found it. At this time, the composition exhibits an excellent control effect over a long period of time at a low dose, not only when it is applied to rice blast at an appropriate time, but also when the application time is delayed. I understood. The present invention is based on this finding.

 Accordingly, an object of the present invention is to provide a drug having an excellent rice blast control effect, 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):

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

Or a compound or an acid addition salt thereof,

 A compound having an inhibitory effect on melanin biosynthesis, and one or more compounds selected from the group consisting of kasugamycin

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 a rice disease controlling agent.

 The bactericidal composition according to the present invention has an excellent control effect on rice diseases, especially on rice blast, and each component acts synergistically to exhibit an unexpected and remarkable control effect. Can be. Therefore, according to the bactericidal composition of the present invention, the amount of applied medicine per area can be reduced. ADVANTAGE OF THE INVENTION According to the bactericidal composition of this invention, compared with the case where the component is used by itself, an excellent control effect can be exhibited by using a smaller dose. The effect is effective for a long time. Therefore, according to the bactericidal composition of the present invention, the number of times of treating plants can be reduced, and the total amount of chemicals used for target plants 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 is expected to make a great contribution to labor saving of agriculture, environmental protection and stability of food production.

[Specific description of the invention]

Bactericidal composition

 As described above, the bactericidal composition according to the present invention comprises at least one compound selected from the group consisting of a compound of the formula (1) or an acid addition salt thereof, a compound having an inhibitory action on melanin biosynthesis, and kasugamycin. And a compound as an active ingredient.

 This fungicidal composition can be used for controlling plant diseases, preferably rice diseases. Such rice diseases include, for example, rice blast, wilt disease caused by sesame leaf blight fungus and streak leaf wilt fungus, discolored rice caused by Curvularia spp. And Alternaria spp. . More preferably, the bactericidal composition according to the present invention is used for controlling rice blast.

Here, “comprising as an active ingredient” includes a carrier corresponding to a desired dosage form. Of course, it may also include other drugs that can be used in combination. 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.

In the formula (1), R represents a hydrogen atom, one COR ¹ヽ -COOR ¹ , -COCH 2 OCH ₃ , or 1 C〇CH ₂ OCOCH ₃ . Where R ¹ is the carbon number :! 4 to 4 alkyl groups. 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). Examples of R ¹ include, for example, a methyl group, E Ji Le group, n- propyl group, and isopropyl building groups or n- butyl. 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. 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 suitable method for forming a bond or introducing a substituent.

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

 [In the above scheme,

R is a hydrogen atom, —COR s -C00R \ —COCH ₂ OCH ₃ , or —C OCH ₂ OCOCH ₃ ;

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

R ² _{is, -R -0R \ - CH 2 OCH} 3 or Ru one CH ₂ 0 C 0 CH ₃ der,.

 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 a compound of the formula (3) or (4) in a base The compound of the formula (1) is obtained by reacting in the presence or absence of a base (step (b)).

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) Thus, a compound of the formula (2) is obtained. The compound of the formula (2) corresponds to the compound of the formula (1) wherein R is a hydrogen atom. The 4_t-butyl-2-fluoroaniline used can be obtained, for example, by a known method described in Chem. Abs. 42, 2329 or J. Chem. Soc, Chem. Co., 1992, 595. Can be

 Step (b):

 Next, when a compound in which R is other than 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, examples of usable bases include organic amines such as triethylamine and pyridine, and inorganic bases such as sodium carbonate, carbonated lime and sodium hydride. The compound of the formula (3) or (4) is preferably 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. Compounds having melanin biosynthesis inhibitory action

As the compound having a melanin biosynthesis inhibitory activity in the present invention, any compound having a melanin biosynthesis inhibitory activity and known in the art can be used. Specifically, for example, fusalide, pyroquilon (1,2,5,6-tetrahydropyro [3,2,1-ij] quinolin-14-one), tricyclazole, carpropamide ((1RS, 3 S) 1,2,2-Dichloromethyl N— [1- (4-chlorophenyl) ethyl] —1-ethyl-3-methylcyclopropanecarboxamide), diclosimeto, phenoxanyl and the like. Preferably, Fusalide, Tricyclazole, Diclosimet, And enoxanil. 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 form such as water-dispersible powder, wettable powder, wettable powder, flowable liquid, liquid, micro capsule, 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, formulation can be carried out by mixing the active ingredient with a solid carrier, a solvent, a surfactant and other adjuvants as required. These carriers and the like can be selected according to the purpose of improving the physical properties of the preparation, stabilizing the active ingredient, and enhancing the efficacy.

 Solid carriers include, for example, clay, talc, calcium carbonate, diatomaceous earth, zeolite, bentonite, acid clay, activated clay, agar palgas clay, bamicularite, perlite, pumice, white carbon, titanium dioxide , Water-soluble salts, wood flour, corn cobs, walnut hulls, powdered cellulose, starch, dextrin, and sugars.

Solvents include, for example, aromatic solvents such as xylene, c ₉ alkyl benzene, c _{1 Q} alkyl benzene, alkyl naphthylene, and high boiling aromatic hydrocarbons; aliphatics such as normal paraffins, isoparaffins, and naphthenes Solvents; mixed solvents such as those produced from kerosene and kerosene; machine oils such as high-boiling aliphatic hydrocarbons; alcohols such as ethanol, isopropanol and cyclohexanol; ethylene glycol, diethylene glycol, propylene glycol Polyhydric alcohols such as propylene glycol glycol, hexylene glycol, polyethylene glycol and propylene glycol; polyhydric alcohol derivatives such as propylene glycol ether; Down like; fatty acid methyl esters (e.g. coconut oil fatty acid methyl ester), And esters such as dibasic acid methyl esters (eg, succinic acid dimethyl ester, glutamic acid dimethyl ester, adipic acid dimethyl ester); nitrogen-containing solvents such as N-alkylpyrrolidone; coconut oil, soybean oil, and rapeseed oil. Such oils and fats; and water.

Examples of the surfactant include sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, sucrose fatty acid ester, polyoxyethylene fatty acid ester, polyoxyethylene fatty acid diester, polyoxyethylene castor oil, polyoxyethylene hardened castor oil , Polyoxyethylene alkyl ether, polyoxyethylene diphenyl ether, polyoxyethylene dialkyl phenyl ether, polyoxyethylene diphenyl ether / formalin condensate, polyoxyethylene / poly Polyoxypropylene block polymer, alkylpolyoxyethylene / polyoxypropylene block polymer ether, alkylphenylpolyxethylene / polyoxypropylene block polymer ether, Polyoxyethylene alkylamine, polyoxyethylene fatty acid amide, polyoxyethylene bisphenyl ether, polyoxyethylene benzyl phenyl ether, polyoxyethylene styryl phenyl ether, polyoxyethylene ether silicon, ester type Nonionic surfactants such as silicon and fluorine-based surfactants, alkyl sulfates, polyoxyethylene alkyl ether sulfates, polyoxyethylene alkyl phenyl ether sulfates, polyoxyethylene benzyl phenyl ether sulfates, polyoxy Ethylene / polyoxypropylene block polymer sulfates, paraffin sulfonates, AOSs, dialkyl sulfosuccinates, alkylbenzene sulfonates, naphthene Sulfonates, naphthene lensulfonate / formalin condensates, alkyl diphenyl terdidisulfonates, lignin sulfonates, polyoxylene ethylene phenyl ether sulfonates, polyoxylene alkyl ether sulfosuccinic acid half esters, fatty acids Salts, N-methyl fatty acid sarcosinates, resinates, polyoxyethylene alkyl ether phosphates, polyoxyethylene alkyl phenyl ether phosphates, polyoxyethylene benzylated phenyl ether phosphates, polyoxy Styrene / polyoxypropylene block polymer phosphates, lecithins, alkyl phosphates, alkyltrimethylammonium chlorides, methyl polyoxyethylene alkylammonium chlorides, alkyl N-methyl-pyridinium Promides, alkylmethylated ammonium chlorides, alkylpentamethylpropylenediamine dichlorides, alkyldimethylbenzalconium chlorides, benzethonium chlorides, dialkyldiaminoethylbetaines, And alkyldimethylbenzyl benzoins.

 Adjuvants include, for example, isopropyl phosphate, carboxymethyl cellulose, PVA, sodium tripolyphosphate, sodium hexamethylene phosphate, xanthan gum, guar gum, carboxyethyl cellulose, sodium benzoate, Potassium sorbate, parahydroxybenzoate, 1,2-benzothiazoline-3-one, ethylene glycol, diethylene glycol, propylene glycol, polyvinylpyrrolidone, urea, hexamethylenetetramine, antioxidant, ultraviolet X-ray absorbers, zeolite, quicklime, magnesium oxide, hydrophobic high-boiling solvents, polyacrylic acid soda, alginic acid, kraft lignin, copolymers of methacrylic acid and vinylpyrrolidone, glycerin, sorbitol, and Water swellable polymer And the like.

 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, a compound having an inhibitory action on melanin biosynthesis, and at least one compound selected from the group consisting of kasugamycin, The amount (active ingredient amount) is 0.1 to 90 parts by weight, preferably 1 to 70 parts by weight, in 100 parts by weight of the bactericidal composition. Good.

The amount of the active ingredient can be appropriately selected in consideration of the preparation form, application method, use environment, and other conditions of the bactericidal composition. For example, when the bactericidal composition is in the form of a wettable powder, the content is 5 to 50% by weight, preferably 10 to 30% by weight, When the bactericidal composition is in the form of a powder, it is 0.5 to 5.0% by weight, preferably 1.0 to 2.0% by weight.

 In the bactericidal composition according to the present invention, the compounding ratio of the compound of the formula (1) or an acid addition salt thereof, a compound having an inhibitory action on melanin biosynthesis, and one or more compounds selected from the group consisting of kasugamycin is as follows: , 1: 100 to 100: 1, preferably 1:20 to 20: 1.

 When the bactericidal composition according to the present invention is used, it may be used directly as it is, but if necessary, it may be diluted with a diluent such as water and sprayed on the area to be treated, mixed, water-applied, It can be subjected to a treatment such as immersion. Examples of such treatment include, for example, application to a plant itself (spray application), application to a nursery box (application of a nursery box), application to soil (soil admixture or lateral application), paddy field Application to water (water 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 diseases, comprising applying an effective amount of the bactericidal composition according to the present invention to an area 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 box, soil, paddy water, or seed. Preferably, the area to be treated is a rice plant, 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, preferably 10 to 100 g, per 10 ares. 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 usually prepared in advance and formulated as described above, and the compound of the formula (1) or the active ingredient in the composition, A pharmaceutical form comprising the acid addition salt, one or more compounds selected from the group consisting of a melanin biosynthesis inhibiting compound, and kasugamycin alone is prepared and used. At this time, these may be mixed and used on the spot.

 Therefore, according to another aspect of the present invention, it comprises a compound of the formula (1) or an acid addition salt thereof, and one or more compounds selected from the group consisting of a compound having a melanin biosynthesis inhibitory action and kasugamycin. A combination is provided.

 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, At least one compound selected from the group consisting of a compound having a synthesis inhibitory action and kasugamycin is provided as a second composition comprising the compound 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 still another aspect of the present invention, there is provided a method for controlling rice diseases, comprising: a compound of the formula (1) or an acid addition salt thereof; a compound having a melanin biosynthesis inhibitory activity; A method is provided that comprises applying one or more selected compounds to an area to be treated.

 In this method, the compound of the formula (1) or an acid addition salt thereof, and one or more compounds selected from the group consisting of a compound having an inhibitory effect on melanin biosynthesis and kasugamycin are added to the region to be treated. The mixture may be applied before application, or the components may be applied separately to the area to be treated. Separate applications include, besides applying each of the components simultaneously to the area to be treated, without prior mixing, adding the compound of formula (1) or an acid addition salt thereof prior to the other component. This includes applying and applying the compound of formula (1) or an acid addition salt thereof after the other component.

According to still another preferred embodiment of the present invention, there is provided a method for controlling rice disease, comprising a compound of the formula (1) or an acid addition salt thereof as an active ingredient: a first composition When,

 A second composition comprising, as an active ingredient, one or more compounds selected from the group consisting of a compound having a melanin biosynthesis inhibitory action and kasugamycin, and A method 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)

 A compound of the formula (1) having a substituent as shown in Table 1 below (Compound 1) was produced.

The production of compound 11 was specifically performed according to the following procedure. Production of 4-t-butyl-1-2-fluoroaniline

To acetonitrile (200 ml) was added SELECTFLUOR (manufactured by Aldrich Chemical Company Inc) (1-methyl-1-methyl-14-fluoro-1,4-diazodiabicyclo [2,2,2] octane-1-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-chloroacetanilide (5.7 g). The mixture was stirred at 100 ° C. for 1 hour, allowed to cool, then 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.) and elution solvent n-hexane-ethyl acetate (10: 1)). 4-t-butyl- 2-fluoro-acetoanilide (3.06 g) was obtained. This 4-t-butyl-12-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 hydrogencarbonate and saturated saline, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure to give 4-t-butyl-2-fluoroaniline ( 3.49 g) were obtained. The ¹ H-NMR spectrum of this compound in a form of chloroform is shown below.

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

The 4-t-butyl-2-fluoroaniline (4.79 g) and 2-methylacetoethyl acetate (4.96 g) obtained according to the above process were added in the presence of trifluoroborolone esterate (0.3 ml). The mixture was refluxed in toluene (60 ml) for 3 hours to obtain a reaction solution. 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 the solvent was distilled off under reduced pressure. The reaction product obtained is converted to a diph: The mixture was refluxed for 1 hour, allowed to cool, and then the precipitated product was collected by filtration under reduced pressure to give 2,3-dimethyl-16-t-butyl-18-fluoro-4-hydroxyquinoline (compound 1) (1. 66 g) was obtained. The ¹ H—N MR data of this compound in heavy DMSO (dimethyl sulfoxide) is shown below.

d (ppm): 11.27 (lH, br.s) ₃ 7.83 (lH, s), 7.59 (lH, br.d) ₃ 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, and then 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 (35.7 mg) was obtained. The ¹ H-NMR data of this compound in double-mouthed form are shown below.

d (ppm): 7.43 (lH , dd), 7.37 (lH, d), 2.78 (3H, s), 2.51 (3H, s), 2.26 (3H 5 s), 1.38 (9H 5 s) Compound 3: 2 , 3-Dimethyl-6-t-butyl-8-fluoro-4-propionylquinoline

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. 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 saturated saline, and then dried over anhydrous sodium sulfate. The lower solvent was distilled off. The obtained crude product is Purified by chromatography (ヮ -gel C-200, elution solvent n-hexane-ethyl acetate (3: 1)), 2,3-dimethyl-6-t-butyl-8-fluoro-1-41 Propionylquinoline (21 mg) (compound 3) was obtained. The ¹ H-NMR data of this compound in form of a micro-mouth are shown below.

d (ppm): 7.42 (lH, dd), 7.36 (lH ₅ d), 2.81 (2H, q), 2.75 (3H, s), 2.25 (3H, s), 1.43 (3H, t), 1.37 (9H ₃ s) Compound 4: 2,3-Dimethyl-6-t-butyl-8-fluoro-4- 4-butyrylquinoline

 60% Sodium hydride (20 mg) was suspended in tetrahydrofuran (3 ml), and Compound 1 (124 mg) was added thereto under ice cooling, followed by stirring for 30 minutes. To this was further added petyryl chloride (200〃1), 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 sodium hydrogen carbonate solution 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 subjected to silica gel chromatography (ヮ -gel C-200, elution solvent n-hexane-ethyl acetate (3:

Purification was performed in 1)) to give 2,3-dimethyl-6-t-butyl-8-fluoro-4-butyrylquinoline (Compound 4) (64 mg). The ¹ H-NMR data of this compound in a double-mouthed form are shown below.

δ (ppm): 7.43 (lH, dd), 7.37 (lH, d) ₅ 2.76 (2H, t), 2.75 (3H ₃ s) ₃ 2.25 (3H ₃ s) ₃

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), and Compound 1 (124 mg) was added thereto under water 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, and then over anhydrous sodium sulfate. After drying, the solvent was distilled off under reduced pressure. 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-16-t- Butyl-8-fluoro-4-valerylquinoline (Compound 5) (12 Omg) was obtained. The ¹ H—N MR data of this compound in deuterated chloroform is shown below.

δ (ppm): 7.42 (lH , dd), 7.37 (lH, d), 2.78 (2H, t), 2.75 (3H, s), 2.25 (3H 3 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-8-fluoro-4-methoxycarbonylquinoline

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. 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 sodium hydrogen carbonate solution and saturated saline, then dried over anhydrous sodium sulfate, and then dried under reduced pressure. The solvent was distilled off. The resulting 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-methoxyethoxyquinoline (Compound 6) (10 Omg) was obtained. A ¹ H-NMR spectrum of this compound in a double-mouthed form is shown below.

5 (ppm): 7.45 (lH , br.s), 7.43 (lH, dd), 4.00 (3H 3 s), 2.76 (3H, s), 2.31 (3H, s), 1.38 (9H, s) Compound 7 : 2, 3-dimethyl-6-t-butyl-8-fluoro-4-ethoxycarbinoquinoline

60% sodium hydride (60 mg) was suspended in tetrahydrofuran (10 ml), and compound 1 (20 Omg) was added thereto under ice cooling, followed by stirring for 30 minutes. Ethyl chloroformate (20 Ojul) was further added thereto, and the mixture was stirred for 3 hours. The obtained reaction solution is poured into ice water, extracted with ethyl acetate, and the ethyl acetate layer is washed with saturated carbonated water. The extract was washed with an aqueous sodium hydrogen carbonate solution and saturated saline, and then dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. 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-1-6-t-butyl-8-fluoro-4-ethoxyethoxycarbonylquinoline (Compound 7) (22 Omg). The ¹ H-NMR data of this compound in double-mouthed form are shown below.

6 (ppm): 7.45 (lH 5 br.s), 7.43 (lH, dd), 4.40 (2H, q, J = 6.7Hz), 2.32 (3H, s,),

2.04 (3H, s), 1.44 (3H, t), 1.38 (9H, s) Compound 8: 2,3-dimethyl-6-t-butyl-8-fluoro-4 1-normal propoxycarbonylquinoline

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. This is further added poured into ice-water for 3 hours stirred _c resulting reaction solution chloroformate normal propyl (200〃1), this was extracted with acetic acid Echiru, saturated with saturated sodium hydrogen Natoriumu aqueous acetic Echiru layer 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 was purified by silica gel chromatography (ヮ -gel C-200, elution solvent n-hexane-ethyl acetate (3: 1)) to give 2,3-dimethyl-6- 4-tert-butyl-8-fluoro-1-n-propoxycarbonylquinoline (Compound 8) (96 mg) was obtained. A ¹ H-NMR spectrum of this compound in a double-mouthed form is shown below. δ (ppm): 7.45 (lH, br.s) ₃ 7.43 (lH, dd), 4.35 (2H, t, J = 6.7 Hz), 2.75 (3H, s), 2.31 (3H, s), 1.82 (2H , m), 1.38 (9H, s), 1.04 (3H 5 t) compound 9: 2, 3-dimethyl - 6- t-butyl - 8 Furuoro 4 one normal butoxycarbonyl two Rukinorin

60% sodium hydride (60 mg) was suspended in tetrahydrofuran (10 ml), and compound 1 (20 mg) was added thereto under ice-cooling, followed by stirring for 30 minutes. Normal butyl chloroformate (2001) was further added thereto and 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 sodium hydrogen carbonate solution and saturated saline, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The crude product obtained 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 mouth—4-Normal butoxycarbonylquinoline (Compound 9) (142 mg) was obtained. The ¹ H-NMR data of this compound in a double-mouthed form are shown below.

(5 (ppm): 7.45 (lH, d), 7.43 (lH, dd), 4.35 (2H, t), 2.75 (3H, s), 2.32 (3H, s) ₅ 1.77 (2H, m) ₅ 1.48 ( 2H, m), 1.38 (9H, s), 0.99 (3H, 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, and the mixture was stirred for 30 minutes. _C was added to methoxyacetyl chloride (200 l). Was added and stirred for 3 hours.c.The reaction solution obtained was poured into ice water, extracted with ethyl acetate, and the ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and saturated saline, and then anhydrous sodium sulfate. After drying on a solvent, the solvent was distilled off under reduced pressure. 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- (methoxyacetylquinoline) (Compound 10) (39 Omg) was obtained. The ¹ H-NMR data of this compound in a double-mouthed form are shown below.

 d (ppm): 7.42 (lH, dd), 7.35 (lH, d), 4.51 (2H, s), 3.62 (3H, s), 2.75 (3H, s), 2.26 (3H, s), 1.37 (9H , s) Compound 11: 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 (20 mg) was added under ice cooling, and the mixture was stirred for 30 minutes. Acetoxyacetyl chloride (1001) 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 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 Monobutyl-18-fluoro-4-acetoxyacetylquinoline (Compound 11) (140 mg) was obtained. A ¹ H-NMR spectrum of this compound in a double-mouthed form is shown below.

6 (w): 7.43 (lH , dd) 5 7.42 (lH, br.s), 5.02 (2H, s), 2.75 (3H, s) 3 2.27 (3H 3 s), 2.23 (3H, s), 1.40 (9H, s) Formulation example

 Formulation Example 1: wettable powder

 The following components were uniformly ground to obtain a wettable powder

 Compound 2 15 parts by weight

 Fusalide 20 parts by weight

 Diatomaceous earth 42 parts by weight

 White carbon 10 parts by weight

 8 parts by weight of polyoxyethylene lauryl ether

 Calcium lignin sulfonate 5 Formulation example 2: Water-dispersible powder

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

 Compound 2 10 parts by weight

 Tricyclazole 10 parts by weight

 Diatomaceous earth 57 parts by weight

 White carbon 10 parts by weight

 8 parts by weight of polyoxyethylene lauryl ether

5 parts by weight calcium lignin sulfonate Formulation Example 3: Wettable powder

The following components were uniformly ground to obtain a wettable powder

 Compound 2 10 parts by weight Diclosimet 3.5 parts by weight Diatomaceous earth 63.5 parts by weight White carbon 10 parts by weight Polyoxyethylene lauryl ether 8 parts by weight Calcium ligninsulfonate 5 parts by weight Formulation example 4: wettable powder

The following components were uniformly pulverized to obtain a wettable powder _c

 Compound 2 10 parts by weight Phenoxanil 10 parts by weight Diatomaceous earth 57 parts by weight White carbon 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 25 5 parts by weight Kasugamycin 1.2 parts by weight Diatomaceous earth 60.8 parts by weight White carbon 0 parts by weight Polyoxyethylene lauryl ether 8 parts by weight lignin sulfonate 5 parts by weight Formulation Example 6: powder

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

22 Compound 2 1.5 parts by weight Fusalide 1.5 parts by weight Clay 96 parts by weight White bonbon 0.5 parts by weight Drilles A (trade name) (manufactured by Kyo Co., Ltd.) 0.5 parts by weight Formulation Example 7: Powder

 The following components were uniformly ground to obtain a powder.

 Compound 2

 Tricyclazole 0 5 parts by weight Clay 97 5 parts by weight White Tokabon 0 5 parts by weight Drilles A (trade name) (manufactured by Sankyo Co., Ltd.) 0 5 parts by weight Formulation Example 8: Dust

 The following components were uniformly ground to obtain a powder.

 Compound 2 1 part by weight Diclosimet 0.15 part by weight Clay 97.85 parts by weight White carbon 0.5 part by weight Drilles A (trade name) (manufactured by Sankyo Co., Ltd.) 0.5 part by weight Formulation Example 9: powder

 The following components were uniformly ground to obtain a powder.

 Compound 2

Phenoxanil 0.6 parts by weight Clay 97.4 parts by weight White carbon 0.5 parts by weight Drilles A (trade name) (manufactured by Sankyo Co., Ltd.) 0.5 parts by weight Formulation Example 10: Powder

 The following components were uniformly ground to obtain a powder.

 Compound 2 1.5 parts by weight Kasugamycin 0.1 part by weight Clay 97.4 parts by weight White carb 0.5 part by weight Drilles A (trade name) (manufactured by Sankyo Co., Ltd.) 0.5 part by weight Evaluation test

 Test A: Rice blast control effect by spraying before infestation (appropriate control test)

 The culture soil was put into a plastic vat (about 30 cm x 50 cm), seeded rice seeds (variety: Koshihikari) that had been germinated, and densely cultivated 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, and when it grew at the 3-4 leaf stage, the rice blast fungus (race 037) A diseased leaf which had been inoculated and infected was 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, lesions were confirmed, and the first application of the drug was performed. The reagent solution used was 20% acetone water or 20% methanol water (as a spreading agent, a 5,000-fold solution of neoesterin (trade name) (manufactured by Kumiai Chemical Industry Co., Ltd.)) was used. The concentration was adjusted to a predetermined concentration, and 15 ml of the solution was sprayed per vat using a spray gun. After 6 to 7 days, the second spraying of the drug was performed in the same manner as the first spraying.

 After the first 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 second spraying, the lesion area on the leaf blade of the lowermost one leaf was observed for 40 strains per byte, and the lesion area ratio of the treated plot was determined. Based on the obtained results and the results obtained in the case of the untreated plot, the control value for each test drug was calculated according to the following formula.

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

 In the test, the drugs listed in the following Tables A1 to A3 were grouped as one group, and each group was completed every 7 °.

The results were as shown in Tables A1 to A3. Table A Drug Concentration (ppm) Lesion area rate Control value Compound 2 80 22. 9 61 Compound 9 80 17.0 71 Compound 10 80 17.97 70 Compound 11 80 161 173 Tricyclazole 80 14.1 76 Diclosimet 80 9.6 84 Compound 2 + Tricyclazole 40 + 40 5.591 Compound 9 + Tricyclazole 40 + 40 3.3 95 Compound 10 + Tricyclazole 40 + 40 2.196 Compound 11 + Tricyclazole 40 + 40 2.196 Compound 2 + diclosime 40 + 40 4.5 92 Compound 9 + diclosime 40 + 40 2.5 96 Compound 10 + diclosime 40 + 40 0.699 Compound 11 + diclosime 40 + 40 1. 1 98 No treatment 59.3 Table A2 Drug concentration (ppm) Lesion area rate Control value Compound 2 80 7.87 78 Compound 9 80 9.971 Compound 10 80 8.5.75 Compound 1 1 80 7.87 78 Fusaride 80 8.37 76 Phunoxanil 80 6.980 Compound 2 + Fusaride 40 + 40 3.490 Compound 9 + Fusaride 40 + 40 1.097 Compound 10 + Fusaride 40 + 40 3.5 90 Compound 1 1 + Fusaride 40 + 40 3.1 9 1 Compound 2 + phenoxanil 40 + 40 2.892 Compound 9 + phenoxanil 40 + 40 2.194 Compound 10 + phenoxanil 40 + 40 1.4 96 Compound 1 1 + phenoxanil 40 + 40 2 . 8 92 No processing 34. 5

Table A 3

Test B: Rice blast control effect by spraying after spread (spray delay test)

 The culture soil was put into a plastic vat (about 30 cm x 50 cm), seeded rice seeds (variety: Koshihikari) that had been germinated, and densely cultivated 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, and when it grew at the 3-4 leaf stage, the rice blast fungus (race 037) A diseased leaf which had been inoculated and infected was 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 lesions were confirmed 7 to 8 days later. After that, they were placed again in a humid condition for 24 hours to promote the secondary transmission and to spread the rice blast in the knots. About three to four days after the spread was promoted, the first drug spraying was performed after the tiny secondary lesions could be confirmed.

Conditions other than those described 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. . The test was performed for each group, with the drugs listed in the following Tables B1 to B4 as one group.

The results were as shown in Tables B1-B4. Table B 1 Drug concentration (ppm) Lesion area ratio Control value Compound 2 80 12.4 84 Compound 10 80 13.4 83 Tricyclazole 80 21.972 Diclosimet 80 16.1 79 Fusaride 80 30.6 61 Phanoxanil 80 17.8 77 Compound 2 + Tricyclazole 40 + 40 3.995 Compound 10 + Tricyclazole 40 + 06, 192 Compound 2 + Diclosimite 40 + 40 4.195 Compound 10 + Diclosimate 40 + 0 1.2 98 Compound 2 + Fusaride 40 + 40 7.091 Compound 10 + Fusaride 40 + 40 5.993 Compound 2 + Phenoxanil 40 + 40 5.693 Compound 10 + Phenoxanil 40 + 40 2.8 97 No processing 78.6

Table B 2 Drug Concentration () 1) Lesion Area Rate Control Value Compound 2 80 12.68 1 Compound 9 80 1 1. 683 Compound 10 80 10. 385 Compound 1 1 80 9. 886 Tricyclazole 80 26, 4 6 1 Diclosimet 80 22.4.67 Compound 2 + Tricyclazole 40 + 40 4.993 Compound 9 + Tricyclazole 40 + 40 5.192 Compound 10 + Tricyclazole 40 + 40 2.8 96 Compound 11 + Tricyclazole 40 + 40 3.195 compound 2 + diclosime 40 + 40 2.5 96 compound 9 + diclosime 40 + 402, 197 compound 10 + diclosime 40 + 40 4.693 compound 1 1 + diclosime 40 + 40 1, 3 98 No processing 67.8

Table B 3 Drug Concentration (ppm) Lesion Area Ratio Control Value Compound 9 80 10.380 Compound 1 1 80 8.88 83 Tricyclazole 80 16.4 68 Dichlosime 80 17.8 66 Fusalide 80 2 1 · 5 59 Phenoxanil 80 19.06 63 Compound 9 + Tricyclazole 40 + 40 4.6 9 1 Compound 11 + Tricyclazole 40 + 40 5.090 90 Compound 9 + Diclosime 40 + 40 1.4 97 Compound 1 1 + Diclosime 40 +40 2.9994 Compound 9 + Fusalide 40 + 40 6.4.888 Compound 11 + Fusalide 40 + 40 5.68 89 Compound 9 + Phenoxanil 40 + 40 2.196 Compound 1 1 + Phenoxanil 40 + 40 4. 1 92 No processing 5 1. 9

Table B4 Drug concentration (ppm) Lesion area rate Control value Compound 2 80 23.5.65 Compound 9 80 22.3 67 Compound 10 80 18.972 Compound 1 1 80 17.8 74 Kasugamycin 20 18.4.73 Compound 2 + Kasugamycin 40 + 10 2.397 Compound 9 + Kasugamycin 40 + 10 0.299 96 Compound 10 + Kasugamycin 40 + 10 0.997 Compound 11 + Kasugamycin 40 + 10 0.25 96 Untreated 68

Claims

Scope of request The following formula (1)

[Wherein, R is a hydrogen atom, —COR—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,

 One or more compounds selected from the group consisting of compounds having a melanin biosynthesis inhibitory action and kasugamycin

A bactericidal composition comprising, as an active ingredient.

2. The bactericidal composition according to claim 1, wherein the compound having a melanin biosynthesis inhibitory activity is selected from the group consisting of fusalide, pyroquilon, tricyclazole, carpropamide, diclosimet and phenoxanil.

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

4. The fungicidal composition according to claim 3, wherein the rice disease is rice blast.

5. The following formula (1)

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

Or a compound or an acid addition salt thereof,

 A compound having an inhibitory action on melanin biosynthesis, and one or more compounds selected from the group consisting of kasugamycin

A combination.

6. Use of a bactericidal composition according to claim 1 or 2 or a combination according to claim 5 for the manufacture of a rice disease control agent.

7. The use according to claim 6, wherein the rice disease is rice blast.

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

9. A method for controlling rice diseases,

The following equation (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 —COCH ₂ OCOCH ₃ ]

Or a compound or an acid addition salt thereof,

 One or more compounds selected from the group consisting of compounds having a melanin biosynthesis inhibitory action and kasugamycin

Applying to the area to be processed.

10. The method according to claim 9, wherein each component is applied to an area to be processed simultaneously.

11. The method according to any one of claims 8 to 10, wherein the rice disease is rice blast.

12. The method according to any one of claims 8 to 11, wherein the area to be treated is a rice plant, soil, or paddy water.