TW200418384A - Fungicidal composition for controlling diseases of paddy rice - Google Patents

Abstract

The present invention relates to a fungicidal composition comprising as active ingredients a compound of formula (1), wherein R represents a hydrogen atom; - COR1 or -COOR1, wherein R1 represents an alkyl group having 1 to 4 carbon atoms; -COCH2OCH3; or -COCH2OCOCH3, or an acid addition salt thereof, and at least one compound selected from the group consisting of strobilurin fungicides. This fungicidal composition is useful for controlling diseases of paddy rice.

Description

200418384 Policy and invention [Technical field to which the invention belongs] The present invention relates to a fungicidal composition having excellent control effects against rice diseases, and more particularly to rice having excellent resistance to rice blast Fungicidal composition for controlling effects of fungal diseases. [Prior Art] WO 0 1/922 3 1 (International Publication Date: 2001-12-6) filed by the applicant of this case discloses a compound of formula (1) having excellent fungicidal activity:

Wherein R represents a hydrogen atom; -COR] or -COOR1, wherein R1 represents an alkyl group having 1 to 4 carbon atoms; -COCH2OCH3; or -COCH2OCOCH3. The physico-chemical properties of the active compounds and the preventive effects of the compounds against rice fever are also described in this bulletin. Furthermore, the bulletin states that the above compounds are superior in the therapeutic effect against rice fever, as well as in their residual activity and preventive effect, and this equivalent effect is different from that of traditional rice fever control agents. -4- (2) (2) 200418384 The mechanism of action of the compound represented by formula (1) is not completely solved. However, these compounds are expected to be different, for example, the mechanism of action of conventional rice heat control agents, because the strains that are resistant to kasugamycin, organophosphorus agents and strobilurin compounds can also achieve control effects And, in addition, it can exhibit fungicidal activity without inhibiting melanin biosynthesis in the culture medium. The strobilurin fungicidal compounds have been reported to have excellent control effects or high fungicidal activity against a variety of rice fungal diseases, including rice fever, or a variety of fungal diseases or pathogenic fungi, such as for barley and wheat, plants and fruit trees. Fungal causes of these diseases that cause cultivation problems. The excellent control effects of strobilurin compounds and their mechanism of action have been planted in, for example, Noyaku Handobukku (Handbook of Agricultural Chemistry) 2001 (issued by the Japan Plant Protection Association in 2401), and Ippan Itaku Shiken Seisekisho (-General Contract Inspection Report ) (Published by the Japan Plant Protection Association). Rice fever is the most serious disease in rice cultivation. Rice fever is a plant disease caused by the fungal parasite of Pyricularia, which is a mold and belongs to the deuteromycetes. So far, many excellent control agents and methods have been reported for rice fever. However, in some cases, even after the application of these control agents, rice fever outbreaks may still occur under certain meteorological conditions, such as uncommon cold summers and very long two seasons, and unfavorable cultivation conditions Substandard management such as seedlings and fertilization. For these and other reasons, there is still a need for the development of a preventive preparation that has better control effects against rice fever. In addition, (3) (3) 200418384 outside of the recent increase in the number of farms with sideline operations and the increase in the number of elderly people engaged in agriculture has led to the extension of the period for which disease control can be carried out, and the reduction of labor applications and the number of technologies. Development needs. Furthermore, from the viewpoints of labor saving and reduction in the amount of agricultural chemicals used, there is a need to develop chemical agents that can exhibit the effects of preventing and treating various diseases simultaneously. [Summary of the invention] For the overall effect of the above-mentioned many activities, the duration of these activities, and the results of evaluations, the inventors of the present case have found that the compound (2,3-dimethyl-6-third Butyl-8-fluoro-4-quinolinol derivatives) and a mixture of at least one compound selected from the group consisting of strobilurin fungicides do not affect the activity of each ingredient and At the same time, it can develop synergistic effects against rice fever and show excellent control effects. In addition, in this regard, it was also found that the above-mentioned composition can be applied at the right time, and when the application time has continued beyond the right time, it can still exhibit resistance to rice fever at low doses for a long period of time-a Excellent control effect on representative rice diseases. The present invention has been completed based on these findings. Accordingly, an object of the present invention is to propose a chemical agent which has excellent control effect on rice diseases and can have a long-term excellent control effect at low doses even if the application time is delayed beyond the proper application timing. In one aspect of the invention, a fungicidal composition is provided, which comprises -6- (4) (4) 200418384 as an active ingredient of a compound of formula (1) or an acid addition salt thereof:

Wherein R represents a hydrogen atom; -COR1 or -COOR1, wherein RI represents an alkyl group having J to 4 carbon atoms; -C〇CH2〇CH3; or < 〇 (^ 2〇 (:: 〇 (:: 113 And at least one compound selected from the group consisting of strobilurin fungicides. According to another aspect of the present invention, a method for controlling rice diseases is proposed, which comprises applying an effective amount of the fungicidal composition described above. According to another aspect of the present invention, the amount of the fungicidal composition for producing a rice disease control agent is proposed. The fungicidal composition of the present invention includes two types of action mechanisms and fungicidal effective ranges which are different from each other The fungicidal composition of the present invention has excellent resistance to rice fever and other rice fungal diseases, such as resistance to leaf sheath fever, due to Helminthosporium leaf blight, Cercospora leaf blight Disease or similar caused by ear burn; caused by, for example, Curvularia and Alternaria ((5) 200418384

Alternaria) and discoloration of rice grains, and false smut. According to the fungicidal composition of the present invention, the ingredients in the fungicidal composition work together in a synergistic manner to provide an unexpected and significant control effect. Therefore, according to the fungicidal composition of the present invention, the required chemical application rate per area can be reduced. In addition, according to the fungicidal composition of the present invention, it is possible to achieve an excellent control effect at a lower dose than when each component of the composition is used separately. In addition, in this case, the control effectiveness can last for a long time. Therefore, according to the fungicidal composition of the present invention, the number of plant treatments required can be reduced. Furthermore, the total amount of chemicals used on a target plant during cultivation can be reduced. The fungicidal composition of the present invention can exhibit excellent control effects when applied at the right timing for control treatment, and even when the application time has been delayed beyond the right timing. The fungicidal composition of the present invention can simultaneously control and prevent many kinds of diseases, and at the same time, it can reduce the risk of developing fungal drug resistance. The fungicidal composition of the present invention is expected to greatly contribute to labor saving in agriculture, environmental protection, and stable food manufacturing. [Embodiment] The fungicidal composition As described above, the fungicidal composition of the present invention includes, as an active ingredient, a compound of formula (1) or an acid addition salt thereof and at least one compound belonging to a globulin fungicide. The fungicidal composition can be used to control plant diseases, the better to control rice diseases, and the better to control rice diseases. Examples of such diseases include: rice fever; smut disease caused by Aspergillus blight, Cercospora leaf blight, etc .; caused by, for example, -8- (6) 200418384 Curvularia and Alternaria Discoloration of rice grains; pseudosmut; and leaf sheath fever. More preferably, the fungicidal composition of the present invention is used to control rice fever in the present invention, "included as an active ingredient ..." means that a carrier suitable for the desired formulation can of course be added and, in addition, also Other chemicals can be incorporated which can be combined with the compounds of the invention. "Rice" is used here to cover rice and rice grown in dry fields, and the term "rice hoe" refers to rice cultivated in paddy fields.

Compound of Formula (1) The fungicidal composition of the present invention includes a compound of Formula (1) or an acid addition salt thereof. In formula (1), R represents a hydrogen atom, -COR1, -COOR1, -COCH2OCH3, or -COCH2OCOCH3. In the present invention, the R1 watch

An alkyl group having 1 to 4 carbon atoms. In the present invention, the alkyl group may be any of a linear form, a branched form, and a cyclic form. Furthermore, one or more hydrogen atoms on the alkyl group may be optionally substituted with one or more substituents which may be the same or different. Specific examples of R1 include methyl, ethyl, n-propyl, isopropyl, and n-butyl. In the formula (1), "wherein R represents an ammonia atom", the compound of the formula (1) may have the structure of the formula (2) 'as a tautomer of the compound of the formula (1). To those skilled in the art, compounds of formula (1) encompass compounds of formula (2). -9- (2) (7) 200418384

F In the present invention, the term, acid addition salt, refers to salts that are generally used in the fields of agriculture and horticulture, such as hydrochloride, nitrate, sulfate, phosphate, and acetate.

It should be mentioned that the compounds of formula (I) may be in the form of hydrates or solvates. In the present invention, these hydrates and solvates are also encompassed by the compounds of formula (1). Specific examples of the compound of the formula (1) include compounds 1 to 11 in the working examples described later. Method for producing compound of formula (1) The compound of formula (1) may be introduced by any key formation or substituent

Appropriate methods for synthesis. For example, a compound of formula (丨) 'can be produced from 4-tert-butyl-2-fluoroaniline, which can be synthesized by a conventional method according to the following reaction procedure. -10- 200418384

Where R represents a hydrogen atom, -COR1, -COOR1, -COCH2OCH3, or -C0CH20-C0CH3; r1 represents a courtyard with 1 to 4 carbon atoms; and R2 represents-R1, -OR1, -CH2OCH3, or-CH2OCOCH3 . According to this reaction procedure, a compound of formula (2) (step (a)) is first provided, and if necessary, a compound of formula (2) is reacted with a compound of formula (3) or (4) in the presence or absence of a base (step ( b)) to obtain a compound of formula (1). The above reaction procedure is explained in more detail below. Step (a): First from, for example, 4-tert-butyl-2-fluoroaniline and ethyl 2-methyl-acetamidine, according to J. Am. Chem. Soc. 70, 2402 (1 948) and -11 -(9) 200418384

Tetrahedron Lett. 2 7, 53? 3 (1 9 8 6). The compound of formula (2) corresponds to the compound of formula (丨). 4-Third-butyl-fluoroaniline used here Abs. 42. 2 2 3 9 or j. Chem · Soc ·, 1992, 595 to prepare the conventional method. Step (b) Second, when it is necessary that R in Formula (1) is not a substance, the compound can be prepared by reacting a compound of Formula (2) with Formula (with or without a base. A base that can be used for this Including, for example, organic amines and inorganic bases, such as sodium carbonate, potassium carbonate 3) or (4) the amount of the compound is preferably 1 to 50 equivalents, more preferably 1 to 10 equivalents " The reaction can be carried out in the absence of a solvent or in the presence of monomethylformamide or tetrahydrofuran, which is inert to the reaction. Strobilurin fungicide In the present invention, any of strobilurin fungicides. Hydophiles are used in, for example, Noyaku Handobukku (issued by the Agrochemical Institute of Plant Protection in 2001) and the Agricultural Chemical Manual) (for the preparation of the formula (2) to combine the hydrogen atom of the R table hydrogen atom, such as in Chem C hem. Commun. 3) or (4) compound acids such as triethylamine and pyridine, and sodium hydride. The compound of formula (: (2) is a group I. The organic solvent in step (b), for example, a temperature range of 0 to 140 ° C may be known in the art as a handbook of fungicide fungicides) 200 1 ( Noyaku Yoran (this plant protection association was issued in -12- (10) (10) 200418384 2001) is described as a fungicide. Those skilled in the art can refer to these documents and choose appropriately Strobilurin fungicides. Specific examples of strobilurin fungicides that can be used in the present invention include azooxy strobilurin (azoxystrobill, metominostrobin, kresoxim-methyl, trifloxystrobin). , Orysastrobin, f 1 uoxastrobin, pyraclostrobin, and picoxystrobin. In a preferred embodiment of the present invention, the strobilurin fungicides are selected from the group consisting of white attolium, metominostrobin, and orysastrobin. In a preferred embodiment of the present invention, In the example, the strobilurin fungicide is selected from the group consisting of yatomin and metominostrobin. Other ingredients When the fungicidal composition of the present invention is actually applied, it can be composed of only the above active ingredients Alternatively, the composition can be mixed with, for example, an appropriate formulation carrier or adjuvant to prepare any appropriate formulation, such as wine powder, granules, tinctures, wettable powder, wettable powder Granules, floables, liquid formulations, microcapsules, or emulsifiable concentrates. This can make the fungicidal composition of the present invention suitable for a variety of suitable applications. The formulations can be applied by methods known in general agricultural chemistry and technology Preparation. In particular, for example, formulations can be prepared by mixing active ingredients, if necessary, for example, with solid carriers, solvents, surfactants, and other adjuvants. Carriers and the like can be selected according to the purpose of use, For example, the properties of the formulation are improved, the active ingredient is stabilized and the effectiveness is improved. -13- (11) (11) 200418384 Suitable solid carriers include, for example, clay, talc, calcium carbonate, diatomaceous earth, zeolite , Bentonite, acid clay, activated clay, activated clay, vermiculite, pearlite, pumice, white carbon, titanium dioxide, water-soluble salts, wood flour, corn cob, walnut shell, cellulose powder , Starch, dextrin, and sugars. Examples of solvents that can be used include: aromatic solvents such as xylene, C9 alkylbenzene, Cio alkylbenzene, alkylnaphthalene, and high boiling aromatic hydrocarbons; aliphatic solvents Examples are n-paraffins, isoparaffins, and naphthenes; mixed solvents such as solvents made from tinder or kerosene; motor oils such as high-boiling aliphatic hydrocarbons; alcohols such as ethanol, isopropanol, and cyclohexanol Polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexanediol, polyethylene glycol, and polypropylene glycol; polyhydric alcohol derivatives such as propylene glycol ethers; ketones such as cyclohexanone and r-butyl Lactones; esters such as fatty acid methyl esters (eg, coconut oil fatty acid methyl esters) and diprotonic acid methyl esters (eg, dimethyl succinate, dimethyl amidate, and dimethyl adipate); nitrogen-containing Solvents such as n-alkylpyrrolidone; fats and oils such as coconut oil, soybean oil, and vegetable oil; and water. Examples of surfactants that can be used herein include sorbitan fatty acid esters, sucrose fatty acid esters, polyethylene oxide fatty acid esters, polyethylene oxide fatty acid esters, polyethylene oxide fatty acid diesters, polyethylene oxide sesame oil, Polyoxyethylene hydrogenated ramie oil, polyoxyethylene alkyl ether, polyoxyethylene alkylphenyl ether, polyoxyethylene dialkylphenyl ether, polyoxyethylene alkylphenyl ether / formalin condensate, polyethylene oxide / Polypropylene oxide block polymer ether, alkylphenyl polyoxyethylene / polyoxypropylene block polymer ether, polyoxyethylene alkylamine, polyoxyethylene fatty acid ammonium amines, polyethylene oxide (12) (12) 200418384 Phenyl acid, polyethylene oxide phenyl ether, polyethylene oxide ethyl pan: pentamyl ether, polyethylene oxide ether type silicones, ester type silicones , Fluorine interface diluent or other non-ionic surfactants, alkyl sulfate salts, polyoxyalkyl ether sulfates, polyoxyethylene alkylphenyl ether sulfates, polyoxyzenylbenzylphenyl ether, Polyethylene oxide / polypropylene oxide embedded polymer®

Ictr salt, paraffin sulfonate, AOSs, dialkyl sulfosuccinate,% benzene sulfonate, Tsai sulfonate, naphthalene sulfonate / formalin condensate, Sulfophenyl ether Disulfonate, lignin sulfonate, polyoxyethylene alkyl phenyl ether sulfonate, polyoxyethylene alkyl ether sulfonate phenyl succinate, fatty acid salts, N-methyl-fatty acid muscle Amines, resinates, polyoxyethylene alkyl ether phosphates, polyoxyethylene alkylphenyl ether phosphates, polyoxyethylene benzylated phenyl ether phosphates, polyoxyethylene / polyoxypropylene inserts Segment polymer phosphate, lecithin, alkyl phosphate, alkyltrimethylammonium chloride, methyl chloride / polyoxyethylene alkylamine, alkyl bromide N-methyl-amidine, alkylmethyl Ammonium chloride, alkylpentamethylpropanediamine dichloride, alkyldimethylbenzyl ammonium chloride, phenethoxyammonium chloride, dialkyldiaminoethylbetaine, and alkane Dimethyl benzyl betaine. Adjuvants that can be used for this include, for example, isopropyl phosphate, carboxymethyl cellulose, PV A, sodium tripolyphosphate, sodium hexametaphosphate, xanthan gum, potassium sorbate, para-hydroxybenzoate Class, 1,2-benzothiazolin-3-one, ethylene glycol, diethylene glycol, propylene glycol, polyvinylpyrrolidone, urea, hexamethylenetetramine, antioxidant, ultraviolet absorber, zeolite, quicklime , Magnesium oxide, hydrophobic high boiling solvent, sodium polyacrylate, alginic acid, kraft paper lignin, methacrylic acid / vinyl pyrrolidone copolymer, glycerin, yama-15- (13) (13) 200418384 sorbitol, and water Swelling polymer compounds. The aforementioned carriers, surfactants, dispersants, and adjuvants may be used alone or in combination of two or more kinds selected from the same group or different groups.

C. In the fungicidal composition of the present invention, the mixing ratio of the compound of formula (1) or its acid salt and at least one compound selected from the group consisting of strobilurin fungicides may be such that The total amount (the total amount of the active ingredient) is 0.1 to 90 parts by weight, preferably 1 to 70 parts by weight based on 100 parts by weight of the fungicidal composition. The total amount of the active ingredient can be appropriately selected by considering the formulation of the fungicidal composition, the application method 'using environment, and other conditions. For example, when the fungicidal composition is in the form of a wettable powder, the total amount of the active ingredient is 5 to 50% by weight, preferably 10 to 30% by weight. On the other hand, when the fungicidal composition is in the form of wine powder, the total amount of active ingredients is from 0.5 to 5.0% by weight, preferably from 1.0 to 2.0% by weight. In the fungicidal composition of the present invention, the mixing ratio of the compound of formula (1) or its acid addition salt to at least one compound selected from the group consisting of strobilurin fungicides is 1: 1. 〇 to 1 〇〇: in the range of ;, preferably in the range of 1:20 to 20: 1. When the fungicidal composition of the present invention is used, these forms of the fungicidal composition can be used directly. If necessary, the fungicidal composition can be diluted with a diluent liquid, such as water, followed by treatment, for example, applied to the area to be treated, blended to the area to be treated, applied to the water surface in the area to be treated, or Immerse in the area to be treated. Specific examples of treatment include -16- (14) (14) 200418384 including application to the plant itself (to stems and leaves), to seedling box, to soil loquat (incorporated or applied to the sideband per soil), application Into field water (applied to the water table or applied to general paddy fields), and applied to seeds (seed treatment). According to another aspect of the present invention, a method for controlling rice disease is proposed, which comprises the steps of applying an effective amount of the fungicidal composition of the present invention to an area to be treated. The term `` area to be treated '' means an area which should be treated with the fungicidal composition of the present invention to control rice diseases. Examples of such areas include rice plants, cultivated seedling boxes, soil, field water, and seeds. Preferably, the area to be treated is rice plants, soil or field water. The preferred amount of the fungicidal composition of the present invention can be appropriately varied according to the use environment, the growth state of the target plant, the mixing ratio of the active ingredients, the formula, the application time, the application method, and the target disease to be controlled. Generally, the amount of the fungicidal composition is 1 to 1,500 g, preferably 10 to 150 g, based on the total amount of the active ingredient, per 10,000 square meters (10 ar es). For example, when the fungicidal composition is applied to rice plants, the amount of the fungicidal composition is 5 to 500 g, preferably 10 to 100 g, per 1,000 square meters, based on the total amount of active ingredients. meter. The fungicidal composition of the present invention can be used in the form of a mixture with, for example, other fungicides, insecticides, acaricides, herbicides, plant growth regulators, or fertilizers. Generally, the fungicidal composition of the present invention is formed into a desired formulation in advance in the manner described above. Alternatively, a method may be used in which an active ingredient in the composition is prepared in advance, that is, a compound of formula (1) -17- (15) 200418384 or an acid addition salt thereof with at least one selected from the group consisting of strobilurin A formulation of one of the compounds in the group consisting of a fungicide and a formulation including other active ingredients, and in use, these formulations are mixed together on the spot. Thus, according to another aspect of the present invention, a composition is proposed, which comprises a compound of formula (1) or an acid addition salt thereof and at least one compound selected from the group consisting of strobilurin fungicides.

In a preferred embodiment, in the above composition, the compound of formula (1) or an acid addition salt thereof is in the form of a first composition including the compound of formula (1) or an acid addition salt thereof as an active ingredient. Provided, and at least one compound selected from the group consisting of strobilurin fungicides is provided in the form of a second composition including the at least one compound as an active ingredient. In this case, like the fungicide composition described above, the first composition and the second composition may be of any formulation formula additionally prepared using an appropriate carrier or adjuvant. Such a composition may be provided in the form of a chemical group.

According to another aspect of the present invention, the use of the above combination for the manufacture of a rice disease control agent is proposed. '' The rice disease control agent 〃 includes the fungicidal composition of the present invention. According to yet another aspect of the present invention, a method for controlling rice diseases is provided, comprising the steps of: adding a compound of formula (1) or an acid addition salt thereof and at least one member selected from the group consisting of a strobilurin fungicide The compounds in the group are applied to the area to be treated simultaneously or separately. In this method, "simultaneous application" covers the following specific examples, that is, the compound of formula (1) or an acid addition salt thereof and at least one compound selected from the group consisting of strobilurin fungicides -18- (16) (16) 200418384, which were pre-mixed together, was prepared into a mixture and applied to the target area. '' Separate 〃 application covers the following specific examples, that is, the compound of formula (1) or its acid is not The addition salt is premixed with at least one compound selected from the group consisting of strobilurin fungicides, and the compound of formula (1) or its acid addition salt is applied earlier or slower than the other ingredient In another preferred embodiment of the present invention, a method for controlling rice diseases is proposed, which includes the following steps: (A)-a first composition, which includes a compound of formula (1) or an acid addition salt thereof as Active ingredient, and (B)-a second composition comprising at least one compound selected from the group consisting of strobilurin fungicides as an active ingredient, and applied to the area to be treated. [Embodiment] The following embodiments are The present invention is further elucidated without restricting it intentionally. Production of the compound of formula (1) The compound of formula (1) (compounds 1 to 1 1) having the composition shown in Table 1 below is prepared. -19- (17) (17) 200418384 Table 1 Components R R1 Compound 1 -H Compound 2 -COR1 -ch3 Compound 3 -COR1 — -c2h5 Compound 4 -COR1 • c3h7 Compound 5 -COR1 -C4H9 Compound 6 -COOR1 -ch3 Compound 7 -COOR1 — -C2H5 Compound 8 -COOR1 -C3H7 compound 9 -COOR1 -C4H9 compound 1 0 -COCH2OCH3 compound 1 1 -COCH2OCOCH3 compounds 1 to 1 1 are prepared according to the following procedure. 4-THIRN-butyl-2-fluoroaniline production will be SELECTFLU 0 R (made by A 1 drich Chemical Company Inc.) (1-chloro-methyl-4-fluoro-1,4-diazabicyclo [2,2,2] octane-bis-tetrafluoroborate) (15 g) was added to acetonitrile (200 ml), and the mixture was heated to 70 ° C for 30 minutes to dissolve SELECTFLU OO in acetonitrile. The reaction solution thus obtained was cooled to 60 ° C, and Tributyl-acetanilide (5.7 g) was added to the cooled reaction solution. Mix 20- (18) 200418384 mixture for one hour and then the reaction solution was left to cool. After the cooled reaction solution was added cold water (200 ml), extracted with ethyl acetate (

100 ml, 2 times). The ethyl acetate layer was washed with saturated brine, dried over anhydrous sodium sulfate, and distilled under reduced pressure to remove the solvent. The crude product thus obtained was chromatographed on silica gel (Wako Gel C-200 was manufactured by Wako Pure Chemical Industries, L td ·, and the elution solvent: Zhengjiyuan-ethyl acetate (10: 1) was purified to obtain 4 -Third-butyl-2-fluoroacetanilide (3.06 g). Add this 4-third-butyl-2-fluoroacetanilide (3.67 g) to include ethanol (30 ml) and concentrated hydrochloric acid (1 5 ml) of the mixed solution, and the mixture was stirred at 95 ° C for 2 hours. The reaction solution was left to cool, and the cooled reaction solution was poured into water, neutralized with a saturated aqueous sodium hydrogen carbonate solution, and then ethyl acetate. Extraction. The ethyl acetate layer was washed with a saturated aqueous solution of sodium bicarbonate and saturated brine, and then dehydrated with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 4-tert-butyl-2-fluoroaniline (3.49 g) The 1H-NMR data of this compound in deuterium-chloroform is shown below.

(5 (ppm): 7.01 (1H, dd), 6.95 (1H, dd), 6.73 (1 Η, m), 1.28 (9 Η, s). Compound 1: 2,3-dimethyl -6-Third-butyl-8-fluoro-4-hydroxy D quinoline 4-Third-butyl-2-fluoroaniline (4.79 g) and 2-methyl-acetamidine acetate will be prepared according to the above procedure The ester (4.96 g) was refluxed in toluene (60 ml) in the presence of boron trifluoride etherate (0.3 ml) for 3 hours to prepare a reaction solution. The reaction solution thus obtained was extracted with a saturated aqueous sodium hydrogen carbonate solution and a saturated saline solution. And dehydrated with anhydrous sodium sulfate. Distilled under reduced pressure to remove -21-(19) 200418384. The reaction product was refluxed in phenyl ether (80 ml) for 1 hour, and then allowed to stand for cooling. The precipitated product was collected by filtration under reduced pressure and This gave 2,3-dimethyl-6-third-butyl-8-fluoro-4-hydroxyquinoline (Compound 1, 1.66 g). 1H-NMR of this compound in deuterium-DMSO (dimethylimine) Data are shown below: δ (ppm): 11.27 (lH, br.s), 7.83 (lH, s), 7.59 (1H, br.d), 2.41 (3H, s), 1.96 (3H, s) ,

1.3 .1 (9H, s). Compound 2: 2,3-dimethyl-6-tert-butyl-8-fluoro-4-ethylamidinequinoline

Compound 1 (50 mg) was placed in acetic anhydride (3 ml) and stirred at 120 ° C for 3 hours to prepare a reaction solution. The acetic anhydride was removed from the reaction solution by distillation under reduced pressure. This solution was extracted and washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated saline solution, and then dehydrated with anhydrous sodium sulfate ', and then the solvent was distilled off under reduced pressure. The product was purified by chromatography on silica gel (Wako Gel C-200, eluent: n-hexane-ethyl acetate (5: 1)) to obtain 2,3-dimethyl-6-n-butyl- 8-Fluoro-4-ethylfluorenyl D quinoline (Compound 2, 35.7 mg). The 1H-NMR data of this compound in neon-chloroform is shown below. 5 (ppm): 7.43 (lH, dd), 7.37 (lH, d), 2.78 (3H, s), 2.51 (3H, s), 2.26 (3H, s), 1.38 (9Η, s) ° Compound 3: 2,3-dimethyl-6 tertiary butyl-8 -fluoro-4 · propionyl [1 quinone • 22- (20) (20) 200418384 morpholine suspended in tetrahydrofuran (3 ml) 60% Sodium hydride (20 mg). Compound 1 (124 mg) was added to the suspension under ice cooling, and the mixture was stirred for 30 minutes. Furthermore, propyl chloride (200 microliters) was added thereto, and the mixture was stirred for 3 hours. The reaction solution thus obtained was poured into ice water, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated aqueous solution of sodium bicarbonate and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure. The crude product was purified by chromatography on silica gel (Wako Gel C-2 00, eluent: n-hexane-ethyl acetate (3: 1)) to obtain 2,3-dimethyl-6 tert-butyl -8-Fluoro-4-propanyl D quinoline (compound 3 '21 mg). The W-NMR data of this compound in deuterium-chloroform are shown below. δ (ppm): 7.42 (lH, dd), 7.36 (lH, d), 2.81 (2H, q), 2.75 (3H, s), 225 (3H, s), 1.43 (3H, t), 1 3 7 (9H, s). Compound 4: 2,3-Dimethyl-6, tert-butyl-8-fluoro-4-butyridinofluorene, suspended in tetrahydrofuran (3 ml) at 60 ° / sodium hydride (20 mg). Compound 1 (124 mg) was added to the suspension under ice cooling, and the mixture was stirred for 30 minutes. Furthermore, butylene chloride (200 microliters) was added thereto, and the mixture was stirred for 3 hours. The reaction solution thus obtained was poured into ice water, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated aqueous solution of sodium bicarbonate and saturated brine, and then dried over anhydrous sodium sulfate -23- (21) (21) 200418384. The solvent was removed by distillation under reduced pressure. The crude product was purified by chromatography on silica gel (Wako Gel C-2 00, eluent: n-hexane-ethyl acetate (3: 1)) to obtain 2,3-dimethyl-6 tert-butyl -8 · fluoro-4-butyridinyl D quinoline (Compound 4, 64 mg). The 1 Η-N M R data for this compound in deuterium-chloroform is shown below. 5 (ppm): 7.43 (lH, dd), 7.37 (lH, d) > 2.76 (2H, t) '2.75 (3Η, s), 2.25 (3 Η5 s), 1.94 (2 Η, m ), 1.37 (9H, s), 1.15 (4H, t). Compound 5: 2,3-Dimethyl-6, tert-butyl-8-fluoro-4-pentamidine D quinoline, 60% sodium hydride (20 mg) was suspended in tetrahydrofuran (3 ml). Compound 1 (124 mg) was added to the suspension under ice cooling, and the mixture was stirred for 30 minutes. Further, pentamidine chloride (200 µl) was added thereto, and the mixture was stirred for 3 hours. The reaction solution thus obtained was poured into ice water, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated aqueous solution of sodium bicarbonate and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure. The crude product was purified by chromatography on silica gel (Wako Gel C-200, elution solvent: n-hexane-ethyl acetate (3: 1)) to obtain 2,3-dimethyl-6 tert-butyl- 8-fluoro-4-pentamylquinoline (compound 5, 120 mg). The NMR data of this compound in deuterium-chloroform are shown below. 5 (ppm): 7.42 (lH, dd), 7.37 (lH, d), 2.78 (2H, t), 2.75 (3H, s), 2.25 (3H, s), 1.89 (2Η -24- (22 ) (22) 200418384, m), 1.56 (2H, m), 1.37 (9H, s), 1.03 (3H, t). Compound 6: 2,3-dimethyl-6 tert-butyl -8-Fluoro-4-methoxycarbonyl D quinoline was suspended in tetrahydrofuran (3 ml) at 60% sodium hydride (20 mg). Compound 1 (124 mg) was added to the suspension under ice cooling, and the mixture was stirred for 30 minutes. Further, methyl chloroformate (200 µl) was added thereto, and the mixture was stirred for 3 hours. The reaction solution thus obtained was poured into ice water, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated saline solution, and then dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure. The crude product was purified by chromatography on silica gel (Wako Gel C-200, elution solvent: n-hexane-ethyl acetate (3: 1)) to obtain 2,3-dimethyl-6 tert-butyl- 8-fluoro-4-methoxycarbonylquinoline (compound 6, 100 mg). 1H-NMR data of this compound in deuterium-chloroform are shown below. 5 (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-6 tert-butyl-8-fluoro-4-ethoxycarbonyl D quinoline Suspended in 60% sodium hydride (60 mg) in tetrahydrofuran (10 ml). Compound 1 (200 mg) was added to the suspension -25- (23) (23) 200418384 'under ice cooling and the mixture was stirred for 30 minutes. Further, ethyl chloroformate (200 µl) was added thereto, and the mixture was stirred for 3 hours. The reaction solution thus obtained was poured into ice water, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated saline solution, and then dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure. The crude product was purified by decantation on silica gel (Wako Gel C-200, elution solvent: n-hexane-ethyl acetate (3: 1)) to obtain 2,3-dimethyl-6 tert-butyl- 8-fluoro-4-ethoxycarbonylzanline (compound 7, 220 mg). 1H-NMR data of this compound in deuterium-chloroform are shown below. (5 (ppm): 7.45 (1H, br.s), 7.43 (1 Η, 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 tert-butyl-8 · fluoro-4-n-propoxycarbonyl D quinoline in tetrahydrofuran (3 ml) was suspended in 60% sodium hydride (20 mg). Compound 1 (124 mg) was added to the suspension under ice cooling, and the mixture was stirred for 30 minutes. Furthermore, n-chloroformate was added thereto. Propyl ester (200 µl), and the mixture was stirred for 3 hours. The reaction solution thus obtained was poured into ice water, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was extracted with a saturated aqueous sodium hydrogen carbonate solution and a saturated saline solution, It was then dehydrated with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The crude product was purified by chromatography on silica gel (Wako Gel C-200, eluent: n-hexane-ethyl acetate (3: 1)). 2,3-Dimethyl-6 tert-butyl-8-fluoro-4--26- (24) (24) 200418384 n-propoxyquinoline (Compound 8, 96 mg). This compound is in deuterium-chloroform IH-NMR The data are shown below (5 (ppm): 7.45 (1H, br • s), 7.43 (1 43, dd), 4. 3 5 (2H, t, J: = 6.7 Hz), 2.75 (3H , S), 2.3 1 (3H, s) 1. 82 (2H ,: m;), 1 ί .38 (9H, s), 1.0 4 (3Η, t) ° Compound 9: 2, 3 -2 Methyl-6 second butyl-8-per-4-n-butoxycarbonyl D quinoline was suspended in tetrahydrofuran (10 ml). 60% sodium oxide (60 mg) was floated under ice cooling. 1 (200 mg) was added to the suspension and the mixture was stirred for 30 minutes1. Furthermore, n-butyl chloroformate (200 micro: sh) was added thereto, and the mixture was stirred for 3 hours. The reaction solution thus obtained was It was poured into ice water, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and then dehydrated with sodium sulfate. The solvent was removed under reduced pressure. The crude product was purified by chromatography on silica gel (Wak O Gel C-200, eluent: n-hexane-ethyl acetate (3: 1)) to obtain 2,3-dimethyl-6 tert-butyl -8-fluoro · 4-n-butoxycarbonyl D quinoline (Compound 9, 14 2 mg). The] H-N MR data of this compound in deuterium-chloroform are shown below. δ (ppm): 7.45 (lH, d), 7.43 (lH, dd), 4.35 (2H, t), 2.75 (3H, s), 2.32 (3H, s), 1.77 ( 2H, m), 1.48 (2H, m), 1.38 (9H, s), 0.99 (3H, t) -27- (25) (25) 200418384 compound 1 0: 2 · 3-dimethyl-6 third Butyl-8-fluoro-4 · methoxyethynylhexylline was suspended in tetrahydrofuran (10 ml) and 60% sodium hydride (165 mg) was suspended. Compound 1 (680 mg) was added to the suspension under ice cooling, and the mixture was stirred for 30 minutes. Further, methoxyacetamidine (200 µl) was added thereto, and the mixture was stirred for 3 hours. The reaction solution thus obtained was poured into ice water, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated saline solution, and then dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure. The crude product was purified by chromatography on silica gel (W ak oG e 1 C-2000, eluent: Zhengjiyuan-ethyl acetate (3: 1)) to obtain 2,3-dimethyl- 6Third-butyl-8-fluoro-4-methoxyethylfluorenyl D quinoline (Compound 10,390 mg). The H-N MR data of this compound in deuterium-chloroform are shown below. 5 (ppm): 7.42 (lH, dd), 7.35 (lH, d), 4.51 (2H, s), 3.62 (3H, s), 2.75 (3H, s), 2.26 (3Η, s), 1 .37 (9H, s). Compound 11: 2,3-Dimethyl-6, tert-butyl-8-fluoro-4-ethoxyoxyacetamidoquinoline suspended in 60% sodium tetrahydrofuran (10 mL), 60% sodium hydride (44 mg ). Compound 1 (200 mg) was added to the suspension 'under ice cooling and the mixture was stirred for 30 minutes. Furthermore, acetylammonium acetamidine chloride (100 µl) was added thereto, and the mixture was stirred for 3 hours. The reaction solution thus obtained was poured into ice water, and the mixture was extracted with ethyl acetate. The ethyl -28-(26) (26) 200418384 ethyl acetate layer was washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated saline solution, and then dehydrated with anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure. The crude product was purified by chromatography on silica gel (Wako Gel C-200, elution solvent: n-hexane-ethyl acetate (3: 1)) to obtain 2,3-dimethyl-6 tert-butyl- 8-Fluoro-4-acetamidoethyridinoline (Compound 1 1 '14 0 mg). The 1 H-NMR data of this compound in deuterium · chloroform are shown below. ό (ppm): 7.43 (1H, dd), 7.42 (1H, br.s), 5.〇2 (2H, s), 2.75 (3H, s), 2.27 (3H, s), 2.23 (3H , S), 1.40 (9H, s). Formulation Example Formulation Example 1: Wettable powder The following ingredients were uniformly honed to prepare a wettable powder. Compound 2 2 0 parts by weight Yatomin 20 0 parts by weight diatomaceous earth 2 8 parts by weight white carbon (trade name; manufactured by Shionogi & Co., Ltd.) 1 3 parts by weight polyethylene oxide lauryl ether 1 2 parts by weight 7 parts by weight of calcium ligninsulfonate Formulation Example 2: Wettable powder The following ingredients were uniformly honed to prepare a wettable powder. Compound 2 1 5 parts by weight Yatomin 5 parts by weight • 29- (27) 200418384 Diatomite 4 7 parts by weight white carbon (trade name; manufactured by Shionogi & Co. · LTD.) 1 〇 by weight polyethylene oxide 8 parts by weight of lauryl ether and 5 parts by weight of calcium lignosulfonate Formulation Example 3: Wettable powder The following ingredients were uniformly honed to prepare a wettable powder. Compound 2 2 0 parts by weight Yatomin 10 parts by weight Shixue diatomaceous earth 42 parts by weight clay 5 parts by weight white carbon (trade name; manufactured by Shionogi & Co., LTD.) 10 parts by weight polyethylene oxide lauryl 8 parts by weight of ether and 5 parts by weight of calcium lignosulfonate Formulation Example 4: Wettable powder The following ingredients were uniformly honed to prepare a wettable powder. Compound 2 2 0 parts by weight metominostrobin 2 0 parts by weight diatomaceous earth 37 7 parts by weight white carbon (trade name; manufactured by Shionogi & Co., LTD.) 1 0 parts by weight polyoxyethylene lauryl ether 8 parts by weight lignin 5 parts by weight -30- (28) 200418384 Formulation Example 5: Wettable powder 15 parts by weight 5 parts by weight 4 7 parts by weight 10 parts by weight 10 parts by weight 8 parts by weight 5 parts by weight The following ingredients were uniformly honed to prepare a wettable powder compound 2 metominostrobin diatomite clay white carbon (trade name; Shionogi & Co., LTD.). Polyoxyethylene lauryl ether lignin acid expansion formulation Example 6 : Wettable powder The following ingredients are uniformly honed to prepare a wettable compound. Compound 2 2 0 parts by weight metominostrobin 10 parts by weight 42 parts by weight 5 parts by weight 10 parts by weight 8 parts by weight 5 parts by weight Carbon (trade name; Shionogi & Co., LTD.) Polyoxyethylene lauryl ether calcium lignosulfonate preparation Example 7: Sprinkle powder The following ingredients were uniformly honed to prepare a spray powder. Compound 2 Subtomin -31 · (29) 200418384 clay calcium carbonate white carbon Trade name; manufactured by Shionogi & Co., LTD.) Driless A (trade name; manufactured by SANKYO CO., LTD. Ground honing to prepare sprinkle powder. Compound 2 Attomin clay calcium carbonate white carbon (trade name; manufactured by Shionogi & Co., LTD.) Driless A (trade name; manufactured by SANKYO CO., LTD.) 0.5 1 part by weight * 0.5 part by weight 0.5 part 97 "parts by weight G 5 parts by weight 0.4 part by weight

Formulation Example 9: Powdering The following ingredients were uniformly honed to prepare a powdering. Compound 2 metominostrobin clay calcium carbonate white carbon (trade name; manufactured by Shionogi & Co., LTD.) Driless A (trade name; manufactured by SANKYO CO., LTD.) 1.2 parts by weight 0.5 parts by weight 9 7.1 0.5 parts by weight 0.2 parts by weight 0.5 parts by weight

Formulation Example 1 0: Dusting-32- (30) 200418384 The following compound 2 metominostr clay calcium carbonate white carbon (trade name Driless A (commercial evaluation test A) The rice was cultivated for about 2 weeks with a fever fungus (in densely planted rice for 1 hour. Then the presence of lesions was examined, and the tested Neo-e Industry spreader): The ingredients were uniformly honed to prepare sprinkles. 1 part by weight) bin 0.5 parts by weight 97.1 parts by weight 0.5 parts by weight; manufactured by Shionogi & Co., Ltd.) 0.4 parts by weight; manufactured by SANKYO CO., LTD.) 0.5 parts by weight Tests on the timing of prevention and control of rice fever resistance obtained after application before spreading) Compost was placed in a plastic hoe (approximately 30 cm x 50 cm). Germinated rice seeds (species: KOshihikari) were planted and cultivated in the hoe. This rice was used in the experiments. Glass greenhouses at 25 ° C during the day and 20 ° C at night. When the rice grows to the 3 or 4 leaf stage, the diseased leaves that had been inoculated with rice race 03 7) and developed a rice fever disease are placed in a humidified condition and then inoculated with rice heat fungus 24 to return the rice plants Inside a glasshouse. After 7 or 8 days' observation, the first chemical application is followed. In this case, the middle school liquid was diluted with a 10% acetone aqueous solution (5,000-fold dilution: sterin (trade name); manufactured by KUMIAI CHEMICAL CO., LTD, as an extender added thereto (> diluted to Predetermined concentration. The test-33- (31) (31) 200418384 test chemical liquid prepared in this way was applied with a spray gun in an amount of 15 ml per milliliter. The second chemical application was performed at the Six or seven days after one chemical application, the second chemical application was performed in the same manner as the first chemical application. After the chemical application, the rice was controlled in a glasshouse. During this period At one to two day intervals, the rice was placed under moist conditions for 24 hours to accelerate the development and spread of rice fever. After 10 days after the last chemical application, for each 40 plants, observe one leaf below the uppermost leaf The area of the lesion on the surface of the leaf on the surface, and the percentage of the lesion area in the treated place was determined. In addition, the percentage of the lesion area in the untreated place was also determined in the same manner as the treated place. The results obtained on the ground and the results obtained on the untreated ground were determined by the following equation. Protection 値 = [1-(Percentage of lesion area in the treated area / Percentage of lesion area in the untreated area)] χ100 of the test chemical The preventive effect and residual effect can be determined by the following method 'wherein at the end of a predetermined number of days after treatment with a chemical agent' to observe whether the percentage of lesion area has increased. Based on this, the preventive effect and residual effect are judged based on whether the final protection ratio is increased This test was performed for each group consisting of the chemical agents shown in Tables A1 to A3 below. The chemical application was performed once or twice. The results are shown in Tables A1 to A3. -34- (32) 200418384 Table A 1: Concentration of chemical agent in dual application test, ppm lesion area% Protection 値 Untreated 35.9 Compound 2 80 5.0 86 Subtomin 80 3.0 92 Compound 2 + Subtomin 40 + 40 0.4 99 Table A2: Single administration Concentration of test chemical, ppm lesion area% Protective 値 Untreated 35.8 Compound 2 80 17.9 50 Subtomin 80 20.0 44 Compound 2 + Subtomin 40 + 40 1 0.6 70 -35- (33) (33) 200418384 Table A 3: Concentration of chemical agent in single application test,% of lesion area Protected 値 Untreated 40.6 Compound 2 ------ __80 15.1 63 Compound 3 ----- — 2 1.4 47 Compound 1 1 80 1 8.3 55 Subtomin — 14.1 6 5 Metominostrobin 20.9 49 Compound 2 + Subtomin 4.1 9 0 Compound 3 + Subtomin 6.9 83 Compound 1 1 + Subtomin_1〇 ^ _4 〇5.4 8 7 Compound 2 + Metominostrobin 40 + 40 ~ -___ 10.9 73 Compound 3 + Metominostrobin ----- 40 + 40-13.6 66 Compound 1 1 + Metominostrobin I. ~-40 + 40 14.5 64 Test B: in After the rice fever was spread, the obtained rice fever resistance was applied (delayed application test). Pot compost was placed in a plastic loquat (about 30 cm x 50 cm), and forced budding rice seeds (species: Koshihikari) were planted in the loquat. , Followed by intensive planting. This rice was used in the experiments. -36- (34) 200418384 The rice was cultivated in a glass greenhouse at 25 ° C during the day and at 20 ° C at night for about 2 weeks. When the rice grows to the 3 or 4 leaf stage, the diseased leaves inoculated with the rice fever fungus (race 037) and developed the rice fever disease are placed in densely planted rice, and then placed under humid conditions to inoculate the rice heat fungus. 24 hours. The rice plants are then returned to the glasshouse. After 7 or 8 days, observe the presence of lesions. Thereafter, the rice was placed under humid conditions for another 24 hours to accelerate the second infection and spread of the rice fever in the loquat. About 3 or 4 days after the acceleration of rice fever spread, a very small secondary lesion was identified, followed by the first chemical application. Other test conditions, such as test chemical liquid conditions, application methods, application intervals, rice fever development and control methods after application initiation, and calculation of lesion area%, were the same as those in Test A. At the second chemical application, the chemical application interval was the same as in Test A. The tests were performed for each group consisting of the chemicals shown in Tables B1 to B4 below. The results are shown in Tables B1 to B4. Table B1: Concentration of chemical agent in double application test, PPm lesion area% Protective 値 Untreated 8 1.5 Compound 2 80 27.6 66 Subtomin 80 2 1.4 74 Compound 2 + Subtomin 40 + 40 12.2 85 -37- (35) 200418384 Table B 2: Chemical concentration in single application test, ppm lesion area% Protection 値 Untreated 74.5 Compound 2 80 27.8 63 Subatom 80 54.1 27 Compound 2 + Subatom 40 + 40 19.8 73 Table B 3: Single application Concentration of drug in chemical test, ppm lesion area% Protected 値 Untreated 30.0 Compound 2 80 16.6 45 Subtomin 80 10.9 64 Compound 2 + Subtomin 40 + 40 4.5 85 -38- (36) 200418384 Table B4: Single application Test chemical concentration, ppm lesion area% protection 値 untreated ^ η / J. J compound 2 80 19.0 74 compound 3 80 3 1.3 5 7 compound 1 1 80 27.8 62 subtomin 80 19.0 74 Metominostrobin 80 27.4 63 compound 2 + Subtomin 40 + 40 14.4 80 Compound 3 + Subtomin 40 + 40 13.1 82 Compound 1 1 + Subtomin 40 + 40 12.5 83 Compound 2 + Metominostrobin 40 + 40 11.5 84 Compound 3 + Metominostrobin 40 + 40 15.3 79 Compound 1 1 + Metominostrobin 40 + 40 15.5 79 -39-

Claims (1)

(1) 200418384, patent application scope 1 · A fungicidal composition, which comprises as an active ingredient a compound of formula (1) or an acid addition salt thereof: Wherein R represents a hydrogen atom; -COR1 or -COOR1, wherein R] represents an alkyl group having 1 to 4 carbon atoms; -COCH2OCH3; or -COCH2OCOCH3, and at least one selected from strobilurin fungicidal fungi Compounds in a group of agents. 2. The fungicidal composition according to item 1 of the application, wherein the compound belonging to the strobilurin fungicide is selected from azoxy strobin and metominostrobin. 3. The fungicidal composition according to item 1 or 2 of the scope of patent application, which is used for the control of rice diseases. 4. For example, the fungicidal composition in the scope of patent application No. 1 or 2 is used for the control of rice diseases. 5. The fungicidal composition according to item 3 of the patent application, wherein the disease is rice blast. 6. A composition comprising a compound of formula (1) or an acid addition salt thereof: -40- (2) (2) 200418384 Wherein R represents a gas atom '-COR or -COOR1, wherein r1 represents a fluorenyl group having 1 to 4 carbon atoms, -COCH20CH3; or _c〇CH2〇COCH3; and at least one selected from the group consisting of strobilurin fungicidal fungi Compounds in a group of agents. 7 · —The application of the fungicidal composition as described in item 1 or 2 of the scope of patent application is for the manufacture of rice disease control agents. 8.-The application of the composition as described in item 6 of the scope of patent application, which is used to manufacture rice disease control agents. 9 • Application of items 7 and 8 in the scope of the patent application, where the disease is rice fever. 10. A method for controlling rice diseases, comprising the step of applying an effective amount of a fungicidal composition as described in claim 1 or 2 to the area to be treated. 1 1 · A method for controlling rice diseases, which comprises adding a compound of formula (1) or an acid addition salt thereof: -41-(3) 200418384 Where R represents a hydrogen atom; -COR1 or -COOR1, where R1 has! Alkyl groups of up to 4 carbon atoms; -COCH20CH3; or .c0CH2ococ ::, and at least one compound from the group consisting of strobilurin fungicides, simultaneously or separately Apply to the area to be treated. 12. The method according to item 11 of the scope of patent application, wherein all ingredients are applied to the area to be treated simultaneously. 1 3. The method according to any one of items 10 to 12 in the scope of patent application, wherein the compound belonging to the strobilurin fungicide is selected from the group consisting of subtomin and metominostrobin ° 1 4. The method according to any one of 10 to 12, wherein the disease is a rice disease. 15. The method according to item 13 of the scope of patent application, wherein the disease is rice disease. 16 · The method according to any one of claims 10 to 12, in which the disease is rice fever. 17. The method according to item 13 of the scope of patent application, wherein the disease is rice fever. -42- (4) (4) 200418384 1 8. The method according to item 15 of the scope of patent application, wherein the disease is rice fever. 19. The method according to any one of claims 10 to 12 in the scope of patent application, wherein the area to be treated is the rice plant itself, soil, or field water. 20. The method according to item 13 of the scope of patent application, wherein the area to be treated is the rice plant itself, soil or field water. 2 1. The method according to item 14 of the scope of patent application, wherein the area to be treated is the rice plant itself, soil, or field water. 22. The method of claim 18, wherein the area to be treated is the rice plant itself, soil, or field water. -43- 200418384 柒. (1) The designated representative figure in this case is: None. (2) Brief description of the component representative symbols in this representative figure: 捌 If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: -3-