AU2013202503B2 - Fungicidal composition and method for controlling plant diseases - Google Patents

Abstract

11:\fit\Intrwovn\NRPortbl\DCC\FMT\5030132_l.doc-28 03/2013 To provide a fungicidal composition having stable and high fungicidal effects against cultivated crops infected with plant diseases resulting from plant diseases. A fungicidal composition containing, as active ingredients, (a) a benzoylpyridine derivative represented by the formula (I) or its salt: wherein when A is -N=, B is -CX 4=; when A is -CH=, B is -N=; each of XI and X2 which are independent of each other, is a halogen atom, an alkoxy group, a hydroxyl group, an alkyl group, a CF 3 group or an alkylthio group; X3 is a hydrogen atom, a halogen atom, an alkoxy group, an alkyl group, a CF 3 group or an alkylthio group; X4 is a hydrogen atom, a halogen atom, an alkoxy group, an alkyl group, a CF3 group or an alkylthio group; R' is an alkyl group; R2' is an alkoxy group; p is 0, 1 or 2; and each of R2" and R2 is an alkoxy group, and (b) at least one additional fungicide.

Description

H:\fmt\1ntenvoven\NRPottbl\DCC\FMT5030088 I.DOC-28/03/2013 1 FUNGICIDAL COMPOSITION AND METHOD FOR CONTROLLING PLANT DISEASES This is a divisional of Australian Patent Application No. 2009266746, the entire contents of which are incorporated herein by reference. TECHNICAL FIELD 5 The present invention relates to a fungicidal composition useful as an agricultural and horticultural fungicide having remarkably improved preventive and/or curative effects against plant diseases, and a method for controlling plant diseases by using such a composition. BACKGROUND ART Patent Document 1 discloses that a benzoylpyridine derivative which is an active ingredient 10 of the fungicidal composition in the present invention is useful as a fungicide and may be used in combination with another fungicide as the case requires. Further, Patent Document 2 discloses that in combination with another fungicide, it is possible to obtain a fungicidal composition having a remarkably excellent synergic effect. However, it has not been known that the composition in the particular combination of the present invention has a remarkably excellent fungicidal effect. 15 Patent Document 1: W002/02527 Patent Document 2: W02005/041663 DISCLOSURE OF THE INVENTION Each of benzoylpyridine derivatives represented by the formula (I) given hereinafter, may be inadequate in its controlling effect against a specific plant disease, its residual effect may last 20 only a relatively short time, or its rainfastness may be weak, and thus, depending upon the application site, it may practically have only an inadequate controlling effect against plant diseases. The present inventors have conducted research and as a result, found that when a benzoylpyridine derivative represented by the formula (1) given hereinafter and a specific fungicide are used in combination, an unexpectedly excellent fungicidal effect can be obtained as compared 25 with a case where the respective compounds are used alone. That is, the present invention relates to a fungicidal composition containing, as active ingredients, (a) a benzoylpyridine derivative represented by the formula (1) or its salt: X3 X1 R O ... ( R32)p ---- /32" A R B R2' X2 wherein when A is -N=, B is -CX 4 =; when A is -CH=, B is -N=; each of X 1 and X 2 which are 30 independent of each other, is a halogen atom, an alkoxy group, a hydroxyl group, an alkyl group, a

CF

3 group or an alkylthio group; X 3 is a hydrogen atom, a halogen atom, an alkoxy group, an alkyl group, a CF 3 group or an alkylthio group; X 4 is a hydrogen atom, a halogen atom, an alkoxy group, an alkyl group, a CF 3 group or an alkylthio group; R 1 is an alkyl group; R 2 is an alkoxy H:\ec\lneneoven\NRPortb\DCC\REC5860500_.doc- 12/12/2013 -2 2" 2 group; p is 0, 1 or 2; and each of R and R is an alkoxy group, and (b) at least one fungicide selected from the group consisting of pyraclostrobin, boscalid, penthiopyrad, pyribencarb, meptyldinocap, difenoconazole, dodine, sulfur, flutianil, 6-t-butyl-8-fluoro-2,3-dimethylquinolin-4-yl acetate and a compound represented by the formula (II):

CH

3 F F N N'.N F 5 Cl N' N In another aspect the present invention relates to a fungicidal composition containing, as active ingredients, (a) a benzoylpyridine derivative selected from 3-(2,3,4-trimethoxy-6 methylbenzoyl)-5-chloro-2-methoxy-4-methylpyridine, 4-(2,3,4-trimethoxy-6-methylbenzoyl)-2,5 dichloro-3-trifluoromethylpyridine, and 4-(2,3,4-trimethoxy-6-methylbenzoyl)-2-chloro-3 10 trifluoromethyl-5-methoxypyridine, and (b) pyribencarb. Further, the present invention relates to a method for controlling plant diseases, which comprises applying the above fungicidal composition to plants. In the formula (1), the halogen atom is fluorine, chlorine, bromine or iodine, and it may, for example, be preferably fluorine, chlorine or bromine. 15 An alkyl moiety in the alkyl group, alkoxyl group and alkylthio group in the formula (1) is preferably C1.6 alkyl (such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl or t-butyl), and among them, C 1

-

4 alkyl is preferred. The benzoylpyridine derivative represented by the formula (1) may form a salt together with an acidic substance, and it may form, for example, an inorganic acid salt such as a hydrochloride, 20 a hydrobromide, a phosphate, a sulfate or a nitrate; or an organic acid salt such as an acetate, a benzoate, a p-toluenesulfonate, a methanesulfonate or a propanesulfonate. The benzoylpyridine derivative represented by the formula (1) may be prepared by production processes as disclosed in Patent Documents 1 and 2. Further, it may be produced also by a method in accordance with Journal of Organic Chemistry., 58, 7832 (1993), and European 25 Journal of Organic Chemistry., 7, 1371-1376 (2001). As the fungicide (b) which is mixed with the benzoylpyridine derivative represented by the above formula (1) or its salt, at least one fungicide may be mentioned which is selected from the group consisting of Pyraclostrobin, Boscalid, Penthiopyrad, Pyribencarb, Meptyldinocap, Difenoconazole, Dodine, Sulfur, flutianil, 6-t-butyl-8-fluoro-2,3-dimethylquinolin-4-y acetate and a 30 compound represented by the formula (11): H: \c\lnterwoen\NRPortbDCC\REC\S586050_Ildc-12t2/2013 - 2a

CH

3 F F N N' F CF N Pyraclostrobin as the fungicide (b) is a compound disclosed in The Pesticide Manual (14th edition; BRITISH CROP PROTECTION COUNCIL) p.900-901. Boscalid is a compound disclosed in The Pesticide Manual (14th edition; BRITISH CROP PROTECTION COUNCIL), p.110. 5 Penthiopyrad is a compound disclosed in The Pesticide Manual (14th edition; BRITISH CROP PROTECTION COUNCIL), p.811. Pyribencarb is a compound disclosed in AG CHEM WO 2010/002026 3 PCT/JP2009/062259 NEW COMPOUND REVIEW, VOLUME 25, 2007, p.58. Meptyldinocap is a compound disclosed in The Pesticide Manual (14th edition; BRITISH CROP PROTECTION COUNCIL) p.356-358. Difenoconazole is a compound disclosed In The Pesticide Manual (14th edition; BRITISH CROP PROTECTION COUNCIL) p.323-325. Dodine is a compound disclosed in The Pesticide Manual 5 (14th edition; BRITISH CROP PROTECTION COUNCIL) p.381-382. Sulfur is a compound disclosed in The Pesticide Manual (14th edition; BRITISH CROP PROTECTION COUNCIL) p.978-979. Flutianil is a compound which Is provisionally registered as ISO 1750, and its CAS No. is 958647-10-4. 6-t-butyl-8-fluoro-2,3-dimethylqunolin-4-y acetate is described in WO 98/55460, Table 1, as compound No. 84 and is a 4-quinolinol derivative. Further, the compound 10 of the formula (II) is a compound disclosed In AG CHEM NEW COMPOUND REVIEW, VOLUME 25, 2007, page 14 as CAS No. 214706-53-3. EFFECT OF THE INVENTION The fungicidal compound of the present Invention has stable and high fungicidal effects for 15 cultivated crops infected with plant diseases, and it is possible to control the plant diseases by this composition. BEST MODE FOR CARRYING OUT THE INVENTION The compound represented by the above formula (1) may be a compound wherein A is 20 CH= and B Is -N= I.e. a compound represented by the formula (1-1): RR2 N R2' X2 wherein X 1 , X 2 , X 3 , R', R 2 ', R 2 " and R'" are as defined above, or a compound wherein A is -N= and B is -CX 4 = I.e. a compound represented by the formula (1-2): R1 X3 X10 - (R N R X4 x2 wherein X 1 , X 2 , X 3 , X 4 , R', R 2 ', R- and R 2 ' are as defined above, Among compounds represented by the above formula (1-1), it is preferred to use at least 25 one compound selected from the group consisting of 3-(2,3,4-trimethoxy-6-methylbenzoyl)-4 bromo-5-chloro-2-methoxypyridine (Compound No. 1), 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5 chloro-4-ethyl-2-methoxypyridine (Compound No. 2), 3-(4,5-dimethoxy-2-methylbenzoyl)-4,5 dichloro-2-methoxypyridine (Compound No. 3), 3-(5-ethoxy-4-methoxy-2-methylbenzoyl)-4,5 dichloro-2-methoxypyridine (Compound No. 4), 3-(2,3,4-trimethoxy-6-methylbenzoyl)-4-bromo-5 30 chloro-2-ethoxypyridine (Compound No. 5), 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-chloro-2 ethoxy-4-methylpyridine (Compound No. 6), 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-bromo-4 chloro-2-ethoxypyridine (Compound No. 7), 3-(2,3,4-trimethoxy-6-methylbenzoyl)-4-chloro-5-iodo 2-methoxypyridine (Compound No. 8), 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-lodo-2,4- WO 2010/002026 4 PCT/JP2009/062259 dimethoxypyridine (Compound No. 9), 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-chloro-2-methoxy 4-methylthiopyridine (Compound No. 10), 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-chloro-2,4 dimethoxypyridine (Compound No. 11), 3-(2,3,4-trlmethoxy-6-methylbenzoyl)-4,5-dibromo-2 methoxypyridine (Compound No. 12), 3-(2,3,4-trimethoxy-6-methylbenzoyl)-4-bromo-2-methoxy 5 5-methylpyridine (Compound No. 13), 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-bromo-4 trifluoromethyl-2-methoxypyridine (Compound No. 14), 3-(2,3,4-trimethoxy-6-methylbenzoyl)-4,5 dichloro-2-methoxypyridine (Compound No. 15), 3-(2,3,4-trimethoxy-6-methylbenzoyl)-2,4 dichloro-5-methylpyridine (Compound No. 16), 3-(2,3,4-trimethoxy-6-methylbenzoyl)-2,4-dichloro 5-lodopyridine (Compound No. 17), 3-(2,3,4-tdmethoxy-6-methylbenzoyl)-2-fluoro-4-lodo-5 10 methylpyddine (Compound No. 18), 3-(2,3,4-trimethoxy-6-methylbenzoyl)-2-fluoro-4,5 dimethylpyridine (Compound No. 19), 3-(2,3,4-tdmethoxy-6-methylbenzoyl)-2-methoxy-4,5 dimethylpyridine (Compounds No. 20), 3-(2-ethoxy-3,4-dimethoxy-6-methylbenzoyl)-2-ethoxy-4,5 dimethylpyridine (Compound No. 21), 3-(2,3,4-trimethoxy-6-methylbenzoyl)-4,5-dimethyl-2 methylthiopyridine (Compound No. 22), 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-bromo-4-chloro 15 2-methoxypyridine (Compound No. 23), 3-(2,3,4-trimethoxy-6-methylbenzoyl)-4-chloro-2 methoxy-5-methylpyridine (Compound No. 24), 3-(2,3,4-trimethoxy-6-methylbenzoyl)-2-chloro-5 trifluoromethyl-4-methylpyridine (Compound No. 25), 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5 trifluoromethyl-2-methoxy-4-methylpyridine (Compound No. 26), 3-(2,3,4-trimethoxy-6 methylbenzoyl)-2,4-dichloro-5-trifluoromethylpyridine (Compound No. 27), 3-(2,3,4-trimethoxy-6 20 methylbenzoyl)-4-chloro-5-trifluoromethyl-2-methoxypyridine (Compound No. 28), 3-(2,3,4 tdmethoxy-6-methylbenzoyl)-5-chloro-4-ethynyl-2-methoxypyridine (Compound No. 29), 3-(2,3,4 trimethoxy-6-methylbenzoyl)-5-chloro-4-fluoromethyl-2-methoxypyridine (Compound No. 30), 3 (2,3,4-trimethoxy-6-methylbenzoyl)-5-bromo-4-fluoromethyl-2-methoxypyridine (Compound No. 31), 3-(2,3,4-trimethoxy-6-methylbenzoyl)-4-fluoromethyl-2-methoxy-5-methylpyrldine (Compound 25 No. 32), 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-chloro-4-difluoromethyl-2-methoxypyd dine (Compound No. 33), 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-ethyl-4-trifluoromethyl-2 methoxypyridine (Compound No. 34), 3-(2,3,4-timethoxy-6-methylbenzoyl)-5-chloro-2-methoxy 4-methylpyridine (Compound No. 35), 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-bromo-2-methoxy 4-methylpyridine (Compound No. 36), 3-(2,3,4-trimethoxy-6-methylbenzoyl)-4-trifluoromethyl-2 30 methoxy-5-methylpyridine (Compound No. 37) and 3-(4,5-dimethoxy-2-methylbenzoyl)-5-chloro 2-methoxy-4-methylpyddine (Compound No. 38). Among them, 3-(2,3,4-trimethoxy-6 methylbenzoyl)-5-chloro-2-methoxy-4-methylpyridine Is most preferred. Among compounds represented by the above formula (1-2), it Is preferred to use at least one compound selected from the group consisting of 4-(2,3,4-trimethoxy-6-methylbenzoyl)-2,5 35 dichloro-3-trifluoromethylpyridine (Compound No. 39), 4-(2,3,4-trimethoxy-6-methylbenzoyl)-2 chloro-3-trifluoromethyl-5-methoxypyridine (Compound No. 40), 4-(2,3,4-trlmethoxy-6 methylbenzoyl)-2-bromo-3-trifluoromethyl-5-methoxypyridine (Compound No. 41), 4-(2,3,4 trimethoxy-6-methylbenzoyl)-2,3,5-trichloropyridine (Compound No. 42), 4-(2,3,4-trimethoxy-6 methylbenzoyl)-3,5-dichloropyridine (Compound No. 43), 4-(2,3,4-trimethoxy-6-methylbenzoyl)-3 40 chloro-5-methoxypyridine (Compound No. 44), 4-(2,3,4-trimethoxy-6-methylbenzoyl)-2-bromo-3 chloro-5-methoxypyridine (Compound No. 45) and 4-(2,3,4-trmethoxy-6-methylbenzoyl)-3 bromo-5-methylpyridine (Compound No. 46). Among them, it is most preferred to use at least one compound selected from the group consisting of 4-(2,3,4-trimethoxy-6-methylbenzoyl)-2,5 dichloro-3-tdfluoromethylpyridine and 4-(2,3,4-trimethoxy-6-methylbenzoyl)-2-chloro-3 45 trifluoromethyl-5-methoxypyridine. The fungicidal composition of the present invention is useful particularly as an agricultural and horticultural fungicide. As the agricultural and horticultural fungicide, it Is effective for WO 2010/002026 5 PCT/JP2009/062259 controlling diseases such as blast, brown spot or sheath blight of rice (Orvza sativa, etc.); powdery mildew, scab, rust, snow mold, snow blight, loose smut, eye spot, leaf spot or glume blotch of cereals (Hordeum vulgare, Tricum aestivum, etc.); melanose or scab of citrus (Citrus spp., etc.); blossom blight, powdery mildew, Alternarla leaf spot or scab of apple (Malus pumila); 5 scab or black spot of pear (Pyrus serotina, Pyrus ussurlensis. Pvrus communis); brown rot, scab or Phomopsis rot of peach (Prunus Dersica, etc.); anthracnose, ripe rot, powdery mildew or downy mildew of grape (Vitis vinifera spp., etc.); anthracnose or brown stem rot of Japanese persimmon (Diospyros kaki, etc.); anthracnose, powdery mildew, gummy stem blight or downy mildew of cucurbit (Cucumis mreo, etc.); early blight, leaf mold or late blight of tomato 10 (Lycopersicon esculentum); various Alternaria disease pathogens of cruciferous vegetables (Brassica sp., Raphanus sp., etc); late blight or early blight of potato (Solanum tuberosum); powdery mildew of strawberry (Fraparia, etc.); and gray mold or disease caused by Sclerotinia of various crops. It is particularly effective against powdery mildew of cereals and vegetables and blast of rice. Further, it is effective also for controlling soil diseases caused by plant pathogens 15 such as Fusarum, Pythium, Rhizoctonia, Verticillium and Plasmodlophora, The plurality of the active ingredients constituting the fungicidal composition of the present Invention are, in the same manner as conventional agricultural chemicals, mixed with various adjuvants and formulated into various formulations such as a dust, granules, water-dispersible granules, a wettable powder, a water-based suspension concentrate, an oil-based suspension 20 concentrate, water soluble granules, an emulsifiable concentrate, a soluble concentrate, a paste, an aerosol and an ultra low-volume formulation. However, so long as the purpose of the present Invention can be accomplished, any type of formulation which is commonly used in this field is applicable. Such adjuvants include solid carriers such as diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaoline, bentonite, a mixture of kaolinite and sericite, clay, 25 sodium carbonate, sodium bicarbonate, mirabilite, zeolite and starch; solvents such as water, toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane, dimethyl sulfoxide, dimethylformamide, dimethylacetamide, N methyl-2-pyrrolidone and alcohol; anionic surfactants and spreaders such as a salt of fatty acid, a benzoate, an alkylsulfosuccinate, a dialkylsulfosuccinate, a polycarboxylate, a salt of alkylsulfuric 30 acid ester, an alkyl sulfate, an alkylaryl sulfate, an alkyl diglycol ether sulfate, a salt of alcohol sulfuric acid ester, an alkyl sulfonate, an alkylaryl sulfonate, an aryl sulfonate, a lignin sulfonate, an alkyldiphenyl ether disulfonate, a polystyrene sulfonate, a salt of alkylphosphoric acid ester, an alkylaryl phosphate, a styrylaryl phosphate, a salt of polyoxyethylene alkyl ether sulfuric acid ester, a polyoxyethylene alkylaryl ether sulfate, a salt of polyoxyethylene alkylaryl ether sulfuric 35 acid ester, a polyoxyethylene alkyl ether phosphate, a salt of polyoxyethylene alkylaryl phosphoric acid ester, and a salt of a condensate of naphthalene sulfonate with formalin; nonionic surfactants and spreaders such as a sorbitan fatty acid ester, a glycerin fatty acid ester, a fatty acid polyglyceride, a fatty acid alcohol polyglycol ether, acetylene glycol, acetylene alcohol, an oxyalkylene block polymer, a polyoxyethylene alkyl ether, a polyoxyethylene alkylaryl ether, a 40 polyoxyethylene styrylaryl ether, a polyoxyethylene glycol alkyl ether, a polyoxyethylene fatty acid ester, a polyoxyethylene sorbitan fatty acid ester, a polyoxyethylene glycerin fatty acid ester, a polyoxyethylene hydrogenated castor oil, and a polyoxypropylene fatty acid ester; and vegetable and mineral oils such as olive oil, kapok oil, castor oil, palm oil, camellia oil, coconut oil, sesame oil, com oil, rice bran oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil, linseed oil, tung oil, 45 and liquid paraffins. Such adjuvants may be selected from known components so long as the purpose of the present Invention can thereby be accomplished. Further, various additives which are commonly used, such as a filler, a thickener, an anti-settling agent, an anti-freezing agent, a WO 2010/002026 6 PCT/JP2009/062259 dispersion stabilizer, a phytotoxicity reducing agent, and an anti-mold agent, may also be employed. The blend ratio of the active ingredient components to the various adjuvants is usually from 0.005:99.995 to 95:5, preferably from 0.2:99.8 to 90:10. In the actual application of such a formulation, It may be used as it is, or may be diluted to a predetermined concentration 5 with a diluent such as water, and various spreaders may be added thereto, as the case requires. A method for controlling plant diseases, which comprises applying the fungicidal composition of the present invention to agricultural and horticultural plants, is also included in the present Invention. The concentration of the fungicidal composition of the present invention can not generally be defined, as it varies depending upon the crop plants to be treated, the application 10 method, the type of the formulation, the dose, etc. However, it is applied in a concentration of the active Ingredients being usually from 0.1 to 10,000 ppm, preferably from 1 to 2,000 ppm in the case of foliage treatment, and usually from 10 to 100,000 g/ha, preferably from 200 to 20,000 g/ha in the case of soil treatment. The formulation containing the fungicidal composition of the present invention or a diluted 15 product thereof may be applied by an application method which is commonly used, such as spreading (spreading, spraying, misting, atomizing, grain diffusing or application on water surface), soil application (such as mixing or Irrigation) or surface application (such as coating, dust coating or covering). Further, It may be applied also by so-called ultra low volume. In this method, the formulation may contain 100% of the active Ingredient. 20 In the fungicidal composition of the present invention, the appropriate mixing weight ratio of the benzoylpyridine derivative (a) represented by the formula (1) or Its salt to another fungicide (b) Is usually from 1:10,000 to 10,000:1, preferably from 1:1,000 to 1,000:1, more preferably from 1:200 to 200:1. 25 EXAMPLES Now, the present Invention will be described in further detail with reference to Examples. However, it should be understood that the present Invention is by no means restricted thereto. TEST EXAMPLE 1: Test on Preventive Effect Against Wheat Powdery Mildew Wheat (cultivar: Norin-61 -go) was cultivated In a plastic pot having a diameter of 7.5 cm, 30 and when it reached 1.5-leaf stage, 10 ml of a chemical solution having each test compound adjusted to a prescribed concentration, was applied by a spray gun in an amount of 1 OOOL/ha. After the chemical solution dried, conidia of Erysiphe araminis were dusted and inoculated and maintained in a constant temperature chamber at 200C. From 6 to 8 days after the Inoculation, the area of sporulation was Investigated, and the disease rate was determined in accordance with 35 the following formula, and the results are shown in Tables 1 to 4. The average lesion area In the non-treated plot was determined in the same manner as for the treated plot except that water was applied by a spray gun Instead of the chemical solution. Disease rate = (a/b) x 100 a: average lesion area In the treated plot 40 b: average lesion area in the non-treated plot Theoretical values were calculated in accordance with the Colby's formula. The fungicidal composition of the present invention has a synergistic effect regarding the test on preventive effect against wheat powdery mildew, when the experimental value is lower than the theoretical value. Theoretical values by the Colby's formula In such cases are shown in brackets in Tables 45 1 to 4.

WO 2010/002026 7 PCT/JP2009/062259 TABLE 1 Concentration of Concentration of compound No. 35 Pyraclostrobin 1.6 ppm 0.8 ppm 0 ppm 400 ppm 7.5(70) 30(70) 100 200 ppm 10(70) 50(70) 100 100 ppm 30(70) 50(70) 100 Oppm T 70 70 100 TABLE 2 Concentration of Concentration of compound No. 39 Pyraclostrobin 6.3 ppm 3.1 ppm 1.6 ppm 0 ppm 400 ppm 5(60) 10(75) 60(85) 100 200 ppm 7.5 (60) 50 (75) 70 (85) 100 100 ppm 50 (60) 60 (75) 70 (85) 100 oppm 60 75 85 100 5 TABLE 3 Concentration of Concentration of compound Pyal1toi No. 40 Pyraclostrobin 0.8 ppm 0 ppm 400 ppm 10(50) 100 200 ppm 30(50) 100 0 ppm 50 100 TABLE 4 Concentration of Concentration of compound No. 35 Difenoconazole 6.3 ppm 3.1 ppm 1.6 ppm 0.8 ppm 0 ppm 50 ppm 5(24) 10 (40) 30(40) 30(40) 40 25 ppm 5 (42) 8 (70) 50(70) 50 (70) 70 12.5 ppm 8 (51) 50 (85) 50(85) 60(85) 85 0 ppm 60 100 100 100 98 TEST EXAMPLE 2: TEST ON PREVENTIVE EFFECTAGAINST CUCUMBER POWDERY 10 MILDEW Cucumber (cultivar: Suyo) was cultivated in a plastic pot having a diameter of 7.5 cm, and when It reached 1.5-leaf stage, 10 ml of a chemical solution having the compound of the present invention adjusted to a prescribed concentration, was applied by a spray gun. After the chemical solution dried, a suspension of conidia of Sphaerotheca cucurbitae was sprayed and 15 inoculated and maintained in a constant temperature chamber at 20 0 C. From 9 to 10 days after the inoculation, the area of sporulation was investigated, and the disease rate was determined In the same manner as in Test Example 1, and the results are shown in Tables 5 to 20. The average lesion area in the non-treated plot was determined in the same manner as for the treated plot except that water was applied by a spray gun Instead of the chemical solution. 20 Further, theoretical values by the Colby's formula are shown in brackets In Tables 5 to 20. TABLE 5 Concentration of Concentration of compound No. 35 Pyribencarb 6.3 ppm 0.8 ppm 0 ppm 50 ppm 5.4 (12.3) 43.8 (58.4) 63.2 25 ppm 4.9 (12.3) 48.7 (58.4) 63.2 12.5 ppm 2.9 (14.2) 43.8 (67.5) 73.0 0 m 19.5 92.4 97.3 WO 2010/002026 8 PCT/JP2009/062259 TABLE 6 Concentration of Concentration of compound No. 39 Pyribencarb 12.5 ppm 6.3 ppm 0 ppm 50 ppm 14.6 (36.9) 24.3 (55.4) 63.2 25 ppm 19.5(36.9) 34.1 (55.4) 63.2 12.5 ppm 24.3 (42.6) 29.2 (63.9) 73.0 0 ppm 58.4 87.6 97.3 TABLE 7_______ ___ Concentration of Concentration of compound Pyribencarb -3.1 ppm No. 0 ppm 25 ppm 14.6 (24.6) 63.2 12.5 ppm 19.5 (28.4) 73.0 0 ppm 38.9 97.3 5 TABLE 8 Concentration of Concentration of compound No. 35 Boscalld 3.1 ppm 1.6 ppm 0 ppm 25 ppm 0.4 (2.2) 6.5 (12.2) 25.8 12.5 ppm 0.9 (3.7) 8.6 (20.3) 43.0 0 ppm 8.6 47.3 86.0 TABLE 9 Concentration of Concentration of compound No. 39 Boscalid 12.5 ppm 6.3 ppm 0 ppm 25 ppm 4.3 (11.1) 0(13.3) 25.8 12.5 ppm 8.6(18.5) 21.5(22.2) 43.0 0 ppm 43.0 51.6 86.0 TABLE 10 Concentration of Concentration of compound No. 40 Boscalld 3.1 ppm 1.6 ppm 0 ppm 25 ppm 0.4(2.2) 4.3(11.1) 25.8 12.5 ppm 0(3.7) 12.9 (18.5) 43.0 6.3 ppm 2.6 (3.7) 12.9 (18.5) 43.0 0 ppm 8.6 43.0 86.0 10 TABLE 11 Concentration of Concentration of compound No. 35 Penthlopyrad 3.1 ppm 1.6 ppm 0 ppm 0.8 ppm 0.4 (4.4) 17.2(24.4) 51.6 0.4 ppm 0.9 (6.7) 30.1 (36.6) 77.4 0 ppm 8.6 47.3 86.0 TABLE 12 ' Concentration of Concentration of compound Penthlopyrad 6.3 ppm No. 39 0 ppm 1.6 ppm 4.3(8.9) 17.2 0.8 ppm 8.6 (26.6) 51.6 0.4 ppm 34.4 (39.9) 77.4 0 ppm 51.6 86.0 WO 2010/002026 9 PCT/JP2009/062259 TABLE 13 Concentration of Concentration of compound Mepthyldinocap 0.4 ppm No. 35 0 ppm 1.6 ppm 25 (36) 60 0.8 ppm 30 (45) 75 0 ppm 60 100 TABLE 14 Concentration of Concentration of compound Mepthyldlnocap 6.3 ppm 0 ppm 3.1 ppm 20(27) 60 1.6ppm 15(27) 60 0 ppm 45 100 5 TABLE 15 Concentration of Concentration of compound the compound of No. 35 the formula (II) 3.1 ppm 0 ppm 1.6 ppm 5.4 (17.3) 58.7 0.8 ppm 0.5(25.9) 88.1 0 ppm 29.4 97.9 TABLE 16 Concentration of Concentration of compound the compound of No. 39 the formula (II) 12.5 ppm 0 ppm 6.3 ppm 2.2 (3.7) 8.6 3.1 ppm 4.7 (7.4) 17.2 1.6 ppm 21.5 (25.9) 60.2 oppm 43 86 TABLE 17 Concentration of Concentration of compound the compound of No. 40 the formula (II) 3.1 ppm 0 ppm 6.3 ppm 0 (0.74) 8.6 3.1 ppm 0(1.5) 17.2 1.6 ppm 4.3 (5.2) 60.2 0 ppm 8.6 86 10 TABLE 18 Concentration of Concentration of compound No. 35 sulfur 3.1 ppm 1.6 ppm 0.8 ppm 0 PPm 25 ppm 39.2 (60.5) 44.1 (67.2) 44.1 (67.2) 68.6 12.5 ppm 29.4 (77.8)- 49.0(86.4) 58.8 (86.4 88.2 6.3 ppm 29.4 (86.4) 53.9 (96.0) 88.2 (96.0) 98.0 0 ppm 88.2 98.0 98.0 98.0 WO 2010/002026 10 PCT/JP2009/062259 TABLE 19 Concentration of Concentration of compound No. 35 flutianil 6.3 ppm 3.1 ppm 0 ppm 0,025 ppm 0 (4.9) 12.5 (52.0) 65 0.0125 ppm 3 (6.4) 40 (680) 85 0.0063 ppm 3(7.1) 60 (76.0) 95 0 ppm 7.5 80 98.3 TABLE 20 Concentration of 6- Concentration of compound No. 35 t-butyl-8-fluoro-2,3 dimethylquinolin-4- 3.1 ppm 1.6 ppm 0.8 ppm 0.4 ppm 0 ppm y acetate 50 ppm 7.4 (20,3) 14.7(33.8) 29,5(33.8) 14.7 (33.8) 34.4 25 ppm 7.4 (34.8) 34.4 (58.0) 19.7 (58,0) 24.6(58.0) 59.0 12.5 ppm 7.4 (37.7) 29.5 (62.8) 39.3 (62.8) 44.2 (62.8) 63.9 6.3 ppm 29.5 (49.3) 49.2 (82.1) 68.8 (82.1) 68.8 (82.1) 83.6 0 ppm 59.0 98.3 98.3 98.3 98.3 5 Now, Formulation Examples of the present invention will be described below. However, the blend ratio, type of formulation or the like of the present Invention Is by no means restricted to the following Examples. FORMULATION EXAMPLE 1 (a) Kaolin 78 parts by weight 10 (b) Condensate of 0-naphthalenesulfonic acid sodium salt with formalin 2 parts by weight (c) Polyoxyethylene alkylaryl sulfate 5 parts by weight (d) Hydrated amorphous silicon dioxide 15 parts by weight 15 A mixture of the above components, the compound of the formula (1) and Pyraclostrobin are mixed in a weight ratio of 8:1:1 to obtain a wettable powder. FORMULATION EXAMPLE 2 (a) Compound of the formula (1) 0.5 part by weight 20 (b) Pyraclostrobin 0.5 part by weight (c) Bentonite 20 parts by weight (d) Kaolin 74 parts by weight (e) Sodium lignin sulfonate 5 parts by weight An appropriate amount of water for granulation is added to the above components and 25 mixed, and the mixture is granulated to obtain granules. FORMULATION EXAMPLE 3 (a) Compound of the formula (1) 2 parts by weight (b) Pyraclostrobin 3 parts by weight 30 (c) Talc 95 parts by weight The above components are uniformly mixed to obtain a dust.

H:\fmt\lntenvoven\NRPortb\DCC\IMm5030088_l,DOC28/03/2013 10a Throughout this specification and the claims which follow, unless the context requires otherwise, the word "comprise", and variations such as "comprises" and "comprising", will be understood to imply the inclusion of a stated integer or step or group of integers or steps but not the exclusion of any other integer or step or group of integers or steps. 5 The reference in this specification to any prior publication (or information derived from it), or to any matter which is known, is not, and should not be taken as an acknowledgment or admission or any form of suggestion that that prior publication (or information derived from it) or known matter forms part of the common general knowledge in the field of endeavour to which this specification relates.

Claims (4)

1. A fungicidal composition containing, as active ingredients, (a) a benzoylpyridine derivative selected from 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-chloro-2-methoxy-4 5 methylpyridine, 4-(2,3,4-trimethoxy-6-methylbenzoyl)-2,5-dichloro-3 trifluoromethylpyridine, and 4-(2,3,4-trimethoxy-6-methylbenzoyl)-2-chloro-3 trifluoromethyl-5-methoxypyridine, and (b) pyribencarb.

2. The fungicidal composition according to Claim 1, wherein the mixing weight ratio 10 of the benzoylpyridine derivative or its salt (a) to the activity-enhancing ingredient (b) is from 1 :10,000 to 10,000:1.

3. A method for controlling plant diseases, which comprises applying the fungicidal composition as defined in Claim 1 to plants. 15

4. The fungicidal composition according to claim I substantially as hereinbefore described with reference to any one of the Examples.