AU2014218412A1 - Plant disease control composition and method for controlling plant disease by applying the same - Google Patents
Plant disease control composition and method for controlling plant disease by applying the same Download PDFInfo
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- AU2014218412A1 AU2014218412A1 AU2014218412A AU2014218412A AU2014218412A1 AU 2014218412 A1 AU2014218412 A1 AU 2014218412A1 AU 2014218412 A AU2014218412 A AU 2014218412A AU 2014218412 A AU2014218412 A AU 2014218412A AU 2014218412 A1 AU2014218412 A1 AU 2014218412A1
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- 239000000203 mixture Substances 0.000 title claims abstract description 63
- 201000010099 disease Diseases 0.000 title claims abstract description 57
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 57
- 238000000034 method Methods 0.000 title claims description 22
- -1 quinoline compound Chemical class 0.000 claims abstract description 341
- 150000001875 compounds Chemical class 0.000 claims abstract description 220
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims abstract description 19
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 239000004480 active ingredient Substances 0.000 claims abstract 5
- 239000004615 ingredient Substances 0.000 claims description 31
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
- 230000000855 fungicidal effect Effects 0.000 claims description 23
- 239000000417 fungicide Substances 0.000 claims description 11
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 claims description 10
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 claims description 6
- JZFICWYCTCCINF-UHFFFAOYSA-N Thiadiazin Chemical compound S=C1SC(C)NC(C)N1CCN1C(=S)SC(C)NC1C JZFICWYCTCCINF-UHFFFAOYSA-N 0.000 claims description 6
- GGKQIOFASHYUJZ-UHFFFAOYSA-N ametoctradin Chemical compound NC1=C(CCCCCCCC)C(CC)=NC2=NC=NN21 GGKQIOFASHYUJZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000003242 anti bacterial agent Substances 0.000 claims description 6
- 150000003857 carboxamides Chemical class 0.000 claims description 6
- RXDMAYSSBPYBFW-UHFFFAOYSA-N carpropamid Chemical compound C=1C=C(Cl)C=CC=1C(C)NC(=O)C1(CC)C(C)C1(Cl)Cl RXDMAYSSBPYBFW-UHFFFAOYSA-N 0.000 claims description 6
- YEJGPFZQLRMXOI-PKEIRNPWSA-N diclocymet Chemical compound N#CC(C(C)(C)C)C(=O)N[C@H](C)C1=CC=C(Cl)C=C1Cl YEJGPFZQLRMXOI-PKEIRNPWSA-N 0.000 claims description 6
- UFHLMYOGRXOCSL-UHFFFAOYSA-N isoprothiolane Chemical compound CC(C)OC(=O)C(C(=O)OC(C)C)=C1SCCS1 UFHLMYOGRXOCSL-UHFFFAOYSA-N 0.000 claims description 6
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- NMVCBWZLCXANER-UHFFFAOYSA-N pyriofenone Chemical group COC1=C(OC)C(OC)=CC(C)=C1C(=O)C1=C(C)C(Cl)=CN=C1OC NMVCBWZLCXANER-UHFFFAOYSA-N 0.000 claims description 6
- ROZUQUDEWZIBHV-UHFFFAOYSA-N tecloftalam Chemical compound OC(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C(=O)NC1=CC=CC(Cl)=C1Cl ROZUQUDEWZIBHV-UHFFFAOYSA-N 0.000 claims description 6
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 claims description 6
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- BSMFIIDHYMHQLK-UHFFFAOYSA-N (6-tert-butyl-8-fluoro-2,3-dimethylquinolin-4-yl) 2-methoxyacetate Chemical compound C1=C(C(C)(C)C)C=C2C(OC(=O)COC)=C(C)C(C)=NC2=C1F BSMFIIDHYMHQLK-UHFFFAOYSA-N 0.000 claims description 5
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- MGNFYQILYYYUBS-UHFFFAOYSA-N 1-[3-(4-tert-butylphenyl)-2-methylpropyl]piperidine Chemical compound C=1C=C(C(C)(C)C)C=CC=1CC(C)CN1CCCCC1 MGNFYQILYYYUBS-UHFFFAOYSA-N 0.000 claims description 5
- YIKWKLYQRFRGPM-UHFFFAOYSA-N 1-dodecylguanidine acetate Chemical compound CC(O)=O.CCCCCCCCCCCCN=C(N)N YIKWKLYQRFRGPM-UHFFFAOYSA-N 0.000 claims description 5
- YTOPFCCWCSOHFV-UHFFFAOYSA-N 2,6-dimethyl-4-tridecylmorpholine Chemical compound CCCCCCCCCCCCCN1CC(C)OC(C)C1 YTOPFCCWCSOHFV-UHFFFAOYSA-N 0.000 claims description 5
- KWLVWJPJKJMCSH-UHFFFAOYSA-N 2-(4-chlorophenyl)-N-{2-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]ethyl}-2-(prop-2-yn-1-yloxy)acetamide Chemical compound C1=C(OCC#C)C(OC)=CC(CCNC(=O)C(OCC#C)C=2C=CC(Cl)=CC=2)=C1 KWLVWJPJKJMCSH-UHFFFAOYSA-N 0.000 claims description 5
- SOUGWDPPRBKJEX-UHFFFAOYSA-N 3,5-dichloro-N-(1-chloro-3-methyl-2-oxopentan-3-yl)-4-methylbenzamide Chemical compound ClCC(=O)C(C)(CC)NC(=O)C1=CC(Cl)=C(C)C(Cl)=C1 SOUGWDPPRBKJEX-UHFFFAOYSA-N 0.000 claims description 5
- DHTJFQWHCVTNRY-UHFFFAOYSA-N 3-[5-(4-chlorophenyl)-2,3-dimethyl-1,2-oxazolidin-3-yl]pyridine Chemical compound CN1OC(C=2C=CC(Cl)=CC=2)CC1(C)C1=CC=CN=C1 DHTJFQWHCVTNRY-UHFFFAOYSA-N 0.000 claims description 5
- DVFMMTVLRXUNNI-UHFFFAOYSA-N 5-(methoxymethyl)-6-octyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-amine Chemical compound NC1=C(CCCCCCCC)C(COC)=NC2=NC=NN21 DVFMMTVLRXUNNI-UHFFFAOYSA-N 0.000 claims description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 5
- 239000005964 Acibenzolar-S-methyl Substances 0.000 claims description 5
- 239000005764 Dithianon Substances 0.000 claims description 5
- 239000005765 Dodemorph Substances 0.000 claims description 5
- 239000005774 Fenamidone Substances 0.000 claims description 5
- 239000005777 Fenpropidin Substances 0.000 claims description 5
- 239000005778 Fenpropimorph Substances 0.000 claims description 5
- 239000005782 Fluopicolide Substances 0.000 claims description 5
- 239000005804 Mandipropamid Substances 0.000 claims description 5
- 239000005810 Metrafenone Substances 0.000 claims description 5
- IUOKJNROJISWRO-UHFFFAOYSA-N N-(2-cyano-3-methylbutan-2-yl)-2-(2,4-dichlorophenoxy)propanamide Chemical compound CC(C)C(C)(C#N)NC(=O)C(C)OC1=CC=C(Cl)C=C1Cl IUOKJNROJISWRO-UHFFFAOYSA-N 0.000 claims description 5
- XFOXDUJCOHBXRC-UHFFFAOYSA-N N-Ethyl-N-methyl-4-(trifluoromethyl)-2-(3,4-dimethoxyphenyl)benzamide Chemical compound CCN(C)C(=O)C1=CC=C(C(F)(F)F)C=C1C1=CC=C(OC)C(OC)=C1 XFOXDUJCOHBXRC-UHFFFAOYSA-N 0.000 claims description 5
- KYGZCKSPAKDVKC-UHFFFAOYSA-N Oxolinic acid Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC2=C1OCO2 KYGZCKSPAKDVKC-UHFFFAOYSA-N 0.000 claims description 5
- 239000005814 Pencycuron Substances 0.000 claims description 5
- 239000005824 Proquinazid Substances 0.000 claims description 5
- 239000005831 Quinoxyfen Substances 0.000 claims description 5
- QNVSXXGDAPORNA-UHFFFAOYSA-N Resveratrol Natural products OC1=CC=CC(C=CC=2C=C(O)C(O)=CC=2)=C1 QNVSXXGDAPORNA-UHFFFAOYSA-N 0.000 claims description 5
- 239000005835 Silthiofam Substances 0.000 claims description 5
- 239000005837 Spiroxamine Substances 0.000 claims description 5
- 239000005845 Tolclofos-methyl Substances 0.000 claims description 5
- LUKBXSAWLPMMSZ-OWOJBTEDSA-N Trans-resveratrol Chemical compound C1=CC(O)=CC=C1\C=C\C1=CC(O)=CC(O)=C1 LUKBXSAWLPMMSZ-OWOJBTEDSA-N 0.000 claims description 5
- 239000005863 Zoxamide Substances 0.000 claims description 5
- UELITFHSCLAHKR-UHFFFAOYSA-N acibenzolar-S-methyl Chemical group CSC(=O)C1=CC=CC2=C1SN=N2 UELITFHSCLAHKR-UHFFFAOYSA-N 0.000 claims description 5
- LFHISGNCFUNFFM-UHFFFAOYSA-N chloropicrin Chemical compound [O-][N+](=O)C(Cl)(Cl)Cl LFHISGNCFUNFFM-UHFFFAOYSA-N 0.000 claims description 5
- WURGXGVFSMYFCG-UHFFFAOYSA-N dichlofluanid Chemical group CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=CC=C1 WURGXGVFSMYFCG-UHFFFAOYSA-N 0.000 claims description 5
- PYZSVQVRHDXQSL-UHFFFAOYSA-N dithianon Chemical compound S1C(C#N)=C(C#N)SC2=C1C(=O)C1=CC=CC=C1C2=O PYZSVQVRHDXQSL-UHFFFAOYSA-N 0.000 claims description 5
- JMXKCYUTURMERF-UHFFFAOYSA-N dodemorph Chemical compound C1C(C)OC(C)CN1C1CCCCCCCCCCC1 JMXKCYUTURMERF-UHFFFAOYSA-N 0.000 claims description 5
- AWZOLILCOUMRDG-UHFFFAOYSA-N edifenphos Chemical compound C=1C=CC=CC=1SP(=O)(OCC)SC1=CC=CC=C1 AWZOLILCOUMRDG-UHFFFAOYSA-N 0.000 claims description 5
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- AMSPWOYQQAWRRM-UHFFFAOYSA-N metrafenone Chemical compound COC1=CC=C(Br)C(C)=C1C(=O)C1=C(C)C=C(OC)C(OC)=C1OC AMSPWOYQQAWRRM-UHFFFAOYSA-N 0.000 claims description 5
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- IWVCMVBTMGNXQD-PXOLEDIWSA-N oxytetracycline Chemical group C1=CC=C2[C@](O)(C)[C@H]3[C@H](O)[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-PXOLEDIWSA-N 0.000 claims description 5
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- FLVBXVXXXMLMOX-UHFFFAOYSA-N proquinazid Chemical compound C1=C(I)C=C2C(=O)N(CCC)C(OCCC)=NC2=C1 FLVBXVXXXMLMOX-UHFFFAOYSA-N 0.000 claims description 5
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- QKJJCZYFXJCKRX-HZHKWBLPSA-N 2-[(2s,3s,6r)-6-[4-amino-5-(hydroxymethyl)-2-oxopyrimidin-1-yl]-3-[[(2s)-2-amino-3-hydroxypropanoyl]amino]-3,6-dihydro-2h-pyran-2-yl]-5-(diaminomethylideneamino)-2,4-dihydroxypentanoic acid Chemical compound O1[C@H](C(O)(CC(O)CN=C(N)N)C(O)=O)[C@@H](NC(=O)[C@H](CO)N)C=C[C@@H]1N1C(=O)N=C(N)C(CO)=C1 QKJJCZYFXJCKRX-HZHKWBLPSA-N 0.000 claims description 4
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- XAMUDJHXFNRLCY-UHFFFAOYSA-N phenthoate Chemical compound CCOC(=O)C(SP(=S)(OC)OC)C1=CC=CC=C1 XAMUDJHXFNRLCY-UHFFFAOYSA-N 0.000 description 1
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 1
- 150000003017 phosphorus Chemical class 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- YFGYUFNIOHWBOB-UHFFFAOYSA-N pirimicarb Chemical compound CN(C)C(=O)OC1=NC(N(C)C)=NC(C)=C1C YFGYUFNIOHWBOB-UHFFFAOYSA-N 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 229920000447 polyanionic polymer Polymers 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229940051841 polyoxyethylene ether Drugs 0.000 description 1
- 229920000056 polyoxyethylene ether Polymers 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- FITIWKDOCAUBQD-UHFFFAOYSA-N prothiofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(Cl)C=C1Cl FITIWKDOCAUBQD-UHFFFAOYSA-N 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 235000021251 pulses Nutrition 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 229940071089 sarcosinate Drugs 0.000 description 1
- HPYNBECUCCGGPA-UHFFFAOYSA-N silafluofen Chemical compound C1=CC(OCC)=CC=C1[Si](C)(C)CCCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 HPYNBECUCCGGPA-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 235000019832 sodium triphosphate Nutrition 0.000 description 1
- YFGAFXCSLUUJRG-WCCKRBBISA-M sodium;(2s)-2-amino-5-(diaminomethylideneamino)pentanoate Chemical compound [Na+].[O-]C(=O)[C@@H](N)CCCN=C(N)N YFGAFXCSLUUJRG-WCCKRBBISA-M 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- NWWZPOKUUAIXIW-FLIBITNWSA-N thiamethoxam Chemical compound [O-][N+](=O)\N=C/1N(C)COCN\1CC1=CN=C(Cl)S1 NWWZPOKUUAIXIW-FLIBITNWSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- POFDSYGXHVPQNX-UHFFFAOYSA-N triazolo[1,5-a]pyrimidine Chemical compound C1=CC=NC2=CN=NN21 POFDSYGXHVPQNX-UHFFFAOYSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000006387 trifluoromethyl pyridyl group Chemical group 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
Landscapes
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Disclosed is a plant disease control composition which has multiple disease spectra 5 against various plant pathogenic bacteria and can exhibit an excellent control effect (a synergistic control effect) that is unpredictable from a single component. The plant disease control composition is characterized by comprising, as active ingredients, at least one 1 2 quinoline compound represented by general formula (I) [wherein R , R independently represent an alkyl group which may be substituted, an aryl group which may be substituted, or 10 the like; R3 and R4 independently represent H, an alkyl group which may be substituted, or the like; X represents a halogen atom, an alkyl group which may be substituted, or the like; Y represents a halogen atom, an alkyl group, or the like; n represents 0 to 4; and m represents 0 to 6] or a salt thereof (group a) and at least one bactericidal compound selected from the group consisting of a strobilurin compound, a triazole compound and others.
Description
- 1 SPECIFICATION PLANT DISEASE CONTROL COMPOSITION AND METHOD FOR CONTROLLING PLANT DISEASE BY APPLYING THE SAME 5 [0001] This application is a divisional of Australian Patent Application No. 2009357098 filed on 22 December 2009, the contents of which are to be taken as incorporated herein by this reference. 10 TECHNICAL FIELD [0001a] The present invention relates to a plant disease control composition which comprises (Group a) at least one quinoline compound represented by the formula (I) or a salt thereof and 15 (Group b) at least one fungicidal compound selected from the group consisting of Group 1 (b 1) to 28 (b-28) as effective ingredients and a method for controlling plant diseases by applying the composition. BACKGROUND ART 20 [0002] A number of chemical agents have heretofore been used for controlling plant diseases. However, the problem that plant pathogens have acquired resistance to the chemical agents becomes remarkable due to frequent use or excessive application, etc., of the chemical agents having similar structures and same functions for controlling the same kinds of diseases. 25 [0003] On the other hand, consumers' needs for agricultural chemical-reduced crops and social needs to reduce environmental loads due to agricultural chemicals have now increased. [0004] Also, in a farmer's field where the chemicals have been actually used, when two or 30 more kinds of chemicals are used in admixture for the treatment by the tank mix method, there are many risks to lower the effect of the other chemical to be mixed with each other or possibilities to cause chemical damages against plant materials depending on a combination of chemicals where they are not well-suited to each other. [0005] - la Under such a situation, it has been desired to develop a plant disease control composition having high effects against fungi or bacteria which are resistant to existing chemicals, and having high effects with a low amount of an effective ingredient. Moreover, for the purpose of preventing plant pathogens from obtaining resistance, it has also been desired to 5 develop a plant disease control composition comprising components (compounds) having different basic structures and different functions with well-suited to each other, and a method for controlling plant diseases. 10006 It has been described in the art that a quinoline compound represented by the 5 formula (I) shows, as a fungicide, controlling effects to rice blast (Pyricularia oryzae) and gray mold (Botrytis cinerea) of tomato, cucumber and kidney bean, etc., by an application method such as seed disinfection, foliar spray treatment, etc. (Patent Literatures I to 4). 100071 10 However, it has never been described in the art yet about a controlling effect of the quinoline compound represented by the formula (1) and the other fungicide(s) in admixture. [Patent Literature 1] WO 2005/070917A [Patent Literature 2] JP 2007-1944A 15 [Patent Literature 3] WO 07/0 11 022A [Patent Literature 41 JP 2007-217353A [0007A) The discussion of documents, acts, materials, devices, articles and the like is included in this specification solely for the purpose of providing a context for the 20 present invention. It is not suggested or represented that any or all of these matters formed part of the prior art base or were common general knowledge in the field relevant to the present invention as it existed before the priority date of each claim of this application. (0007B] 25 Where the terms "comprise", "comprises", "comprised" or "comprising" are used in this specification (including the claims) they are to be interpreted as specifying the presence of the stated features, integers, steps or components, but not precluding the presence of one or more other features, integers, steps or components, or group thereof. 30 DISCLOSURE OF THE INVENTION [00081 The present inventors have investigated a combination of the quinoline compound represented by the formula (1) and the other fungicidal component(s), and as a result, they have found that by combining the quinoline compound represented by the 35 formula (1) and a specific fungicidal compound(s), excellent controlling effects (synergistic effects) against various plant pathogens can be obtained, which could never be expected from the single component alone, stable prophylaxis effect can be obtained against the existing fungi and bacteria resistant to chemicals, and no chemical damage to plants occurred to accomplish the present invention. 5 [0009] An aspect of the present invention is to provide a novel plant disease control composition having a broad spectrum against various kinds of plant pathogens, having high plant disease controlling effects against existing fungi and bacteria resistant to chemicals, showing high activity even when amounts of effective ingredients to be 10 applied to environment where fungi or bacteria are living are low, and showing no chemical damage against plants, and a method for controlling plant disease by appling the composition. 100101 15 The present invention comprises a plant disease control composition containing (Group a) (a) at least one kind of a quinoline compound represented by the general formula (I): [Formula 1 INI 20 [wherein R' and R 2 may be the same or different from each other, and each represents a CI to C 6 alkyl group which may be substituted by the same or different 1 to 3 substituent(s) selected from the group consisting of a halogen atom, a C, to C 6 alkoxyl group, a C, to C 6 alkylthio group and a phenoxy group; an aryl group which may be substituted by the same or different I to 6 25 substituent(s) selected from the group consisting of a halogen atom, a C, to C 6 alkyl group which may be substituted by the same or different I to 3 halogen atom(s), a C, to C, alkoxyl group, an amino group which may be substituted by the same or different 1 or 2 C, to C 6 alkyl group(s) or acyl groupss, a nitro group, a cyano group, a hydroxyl group, a mercapto group and a C, to C 6 alkylthio group; 30 a heteroaryl group which may be substituted by the same or different I to 6 substituent(s) selected from the group consisting of a halogen atom, a C, to C 6 alkyl -3a group which may be substituted by the same or different I to 3 halogen atoms) and a C to C 6 alkoxyl group; or an araikyl group which may be substituted by the same or different I to 6 substituent(s) selected from the group consisting of a halogen atom, a C 1 to C 6 alkyl group which may be substituted by the same or different I to 3 halogen 5 atomss, a C 1 to C 6 alkoxyl group, an amino group which may be substituted by the same or different I or 2 CA to C 6 alkyl group(s) or acyl group(s), a nitro group, a cyano group, a hydroxyl group, a mercapto group and a C to C 6 alkylthio group, or, R' and R2 form, in combination with the carbon atoms to which they are bonded, a C 3 to G 1 o cycloalkyl ring which may be substituted by the same or different I 10 to 3 substituent(s) selected from the group consisting of a halogen atom, a C 1 to C 6 alkyl group, a C 1 to C 6 alkoxyl group and a phenoxy group, R' and R 4 may be the same or different from each other, and each represents -4 a hydrogen atom; a C 1 to C 6 alkyl group which may be substituted by the same or different 1 to 3 substituent(s) selected from the group consisting of a halogen atom, a Ci to C 6 alkoxyl group, a C, to C 6 alkylthio group and a phenoxy group; 5 a halogen atom; a Ci to C 6 alkoxyl group; or a hydroxyl group, or,
R
3 and R 4 form a C to C 6 alkylidene group or an oxo group in combination thereof; or 10 form, in combination with the carbon atoms to which they are bonded, a C 3 to Cio cycloalkyl ring which may be substituted by the same or different 1 to 3 substituent(s) selected from the group consisting of a halogen atom, a C 1 to C 6 alkyl group, a C, to C 6 alkoxyl group and a phenoxy group; X may be the same or different from each other when n is 2 to 4, and each 15 represents a halogen atom; a C 1 to C 6 alkyl group which may be substituted by the same or different 1 to 3 substituent(s) selected from the group consisting of a halogen atom, a Ci to C 6 alkoxyl group, a hydroxyl group, a C 2 to C 7 alkoxycarbonyl group and a phenoxy group; 20 a C 2 to C 6 alkenyl group which may be substituted by the same or different 1 to 3 substituent(s) selected from the group consisting of a halogen atom, a C, to C 6 alkoxyl group, a C 2 to C 7 alkoxycarbonyl group and a phenoxy group; a C 2 to C 6 alkynyl group which may be substituted by the same or different 1 to 3 substituent(s) selected from the group consisting of a halogen atom, a C to C 6 alkoxyl 25 group and a phenoxy group; an aryl group which may be substituted by the same or different 1 to 6 substituent(s) selected from the group consisting of a halogen atom, a C 1 to C 6 alkyl group which may be substituted by the same or different 1 to 3 halogen atom(s), a C 1 to
C
6 alkoxyl group, an amino group which may be substituted by the same or different 1 30 or 2 C 1 to C 6 alkyl group(s) or acyl group(s), a nitro group, a cyano group, a hydroxyl group, a mercapto group and C 1 to C 6 alkylthio group; a heteroaryl group which may be substituted by the same or different 1 to 6 substituent(s) selected from the group consisting of a halogen atom, a C 1 to C 6 alkyl group which may be substituted by the same or different 1 to 3 halogen atom(s) and a 35 CI to C 6 alkoxyl group; a Ci to C 6 alkoxyl group; - 5 an amino group which may be substituted by the same or different 1 or 2 C, to
C
6 alkyl group(s) or acyl group(s); an acyl group; a cyano group; or, 5 an N-hydroxy C 1 to C 6 alkaneimidoyl group the hydrogen atom of the hydroxyl group of which may be substituted by a substituent selected from the group consisting of a C 1 to C 6 alkyl group, a C 2 to C 6 alkenyl group, a C 2 to C 6 alkynyl group, an aralkyl group, an aryl group and a heteroaryl group, Y may be the same or different from each other when m is 2 to 6, and each 10 represents a halogen atom; a C 1 to C 6 alkyl group; a C 1 to C 6 alkoxyl group; or a hydroxyl group, n represents an integer of 0 to 4, and m represents an integer of 0 to 6] 15 or a salt thereof, and [0011] (Group b) (b) one or more fungicides selected from the group consisting of the following mentioned Groups (1) to (28): 20 Group (1) a Strobilurin series compound selected from (b-1-1) Azoxystrobin (b-1-2) Kresoxim-methyl (b-1-3) Pyraclostrobin 25 (b-1 -4) Picoxystrobin (b-1-5) Fluoxastrobin (b-1-6) Dimoxystrobin (b- 1-7) Orysastrobin (b-1-8) Metominostrobin and 30 (b-1-9) Trifloxystrobin, [00121 Group (2) a triazole series compound selected from (b-2-1) Simeconazole 35 (b-2-2) Tebuconazole (b-2-3) Fenbuconazole -6 (b-2-4) Hexaconazole (b-2-5) Imibenconazole (b-2-6) Triadimefon (b-2-7) Tetraconazole 5 (b-2-8) Prothioconazole (b-2-9) Triticonazole (b-2-10) Epoxiconazole (b-2- 11) Ipconazole (b-2-12) Metconazole 10 (b-2-13) Propiconazole (b-2-14) Cyproconazole (b-2-15) Difenoconazole (b-2-16) Diniconazole (b-2-17) Fluquinconazole 15 (b-2-18) Flusilazole (b-2-19) Penconazole (b-2-20) Bromuconazole (b-2-2 1) Triadimenol (b-2-22) Flutriafol 20 (b-2-23) Myclobutanil (b-2-24) Etaconazole and (b-2-25) Bitertanol, [00131 Group (3) 25 an imidazole series compound selected from (b-3-1) Oxpoconazole fumarate (b-3-2) Triflumizole (b-3-3) Imazalil (b-3-4) Imazalil-S 30 (b-3-5) Prochloraz (b-3-6) Pefurazoate and (b-3-7) Triazoxide, 10014] Group (4) 35 a carboxamide series compound selected from (b-4-1) Penthiopyrad -7 (b-4-2) Flutolanil (b-4-3) Furametpyr (b-4-4) Boscalid (b-4-5) Fenhexamid 5 (b-4-6) Cyflufenamid (b-4-7) Tecloftalam (b-4-8) Mandipropamid (b-4-9) Bixafen (b-4-10) Carboxin 10 (b-4-1 1) Oxycarboxin (b-4-12) Mepronil (b-4-13) Silthiofam (b-4-14) Thifluzamide (b-4-15) Flumetover 15 (b-4-16) Ethaboxam (b-4-17) Zoxamide (b-4-18) Tiadinil (b-4-19) Isotianil (b-4-20) Diclocymet 20 (b-4-21) Fenoxanil (b-4-22) Fluopicolide (b-4-23) Fluopyram (b-4-24) Carpropamid (b-4-25) Tolfenpyrad 25 (b-4-26) N-[2-(1,3-dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl- 1 H-pyrazol-4 carboxamide (b-4-27) N-{2-[1,1 '-bi(cyclopropyl)-2-yl]phenyl}-3-(difluoromethyl)-1-methyl-i H pyrazol-4-carboxamide (b-4-28) 3-(Difluoromethyl)-N-(9-isopropyl-1,2,3,4-tetrahydro-1,4-methanonaphthalen 30 5-yl)-l-methyl-IH-pyrazol-4-carboxamide (b-4-29) 3-(Difluoromethyl)-N-[4'-(3,3-dimethylbutyn- 1 -yl)biphenyl-2-yl] -1 -methyl 1 H-pyrazol-4-carboxamide (b-4-30) 3-(Difluoromethyl)-N-[4'-(3-methoxy-3-methylbutyn-1-yl)biphenyl-2-yl]-1 methyl-I H-pyrazol-4-carboxamide and 35 (b-4-31) 3 -(Difluoromethyl)- I -methyl-N-[ 1,2,3,4-tetrahydro-9-(1 -methylethyl)- 1,4 methanonaphthalen-5-yl]-1 H-pyrazol-4-carboxamide, 8 Group (5) an acylalanine series compound selected from (b-SI) Metalaxyl 5 (b-5-2) MetalaxyI-M (b-5-3) Benalaxyl (b-5-4) BenaLaxyl-M (Kiralaxyl) and (b-5-5) Furalaxyl-Mi [00161 10 Group (6) a valineamide series compound selected from (b-6-1) Benthiaivaiicarb-isopropyl and (b-6-2) Iprovalicarb; [0017] 15 Group (7) a sulfoneamide series compound selected from (b-1) Cyazolamid (b-7-2) Amisubromand (b-7-3) Flusulfamid 20 j0018J Group (8) a sulfenarnide series compound selected from (b-S-i) Tolylfluanid and (b-8-2) Dichlofluanid 25 100191 Group (9) a carbamate scales compound selected from (b-9-1) Propamocarb (b-9-2) Propamocarb hydrochloride 30 (b-9-3) Diethofencarb and (b-9-4) Pyribecearb |0020] Group (10) a dithocarbam ate series compound selected from 35 (b-10-1) Manzeb (Mancozeb) (b- 10-2) Mane!, -9 (b-10-3) Propineb (b-10-4) Zineb (b-10-5) Metiram (b-10-6) Ziram 5 (b-10-7) Thiuram and (b-10-8) Polycarbamate [00211 Group (11) a dicarboxylimide series compound selected from 10 (b-I1-1) Iprodione (b- 11-2) Procymidone (b-11-3) Captan (b-I 1-4) Vinclozolin (b-i 1-5) Chlozolinate and 15 (b-11-6) Folpet [0022] Group (12) a guanidine series compound selected from (b-12-1) Iminoctadine trialbesilate 20 (b-12-2) Iminoctadine-triacetate (b-12-3) Guazatine and (b-12-4) Dodine [0023] Group (13) 25 a pyrimidine series compound selected from (b-13-1) Mepanipyrim (b-13-2) Fenarimol (b-13-3) Ferimzone (b-13-4) Cyprodinil 30 (b-13-5) Pyrimethanil (b-13-6) Nuarimol (b-13-7) Dimethirimol (b-13-8) Bupirimate and (b-13-9) Diflumetorim 35 [0024] Group (14) - 10 a morpholine series compound selected from (b-14-1) Dimethomorph (b-14-2) Fenpropimorph (b-14-3) Tridemorph 5 (b-14-4) Dodemorph and (b-14-5) Flumorph [00251 Group (15) a benzimidazole series compound selected from 10 (b-15-1) Thiophanate (b- 15-2) Thiophanatemethyl (b-15-3) Benomyl (b-15-4) Carbendazim (b-15-5) Thiabendazole and 15 (b-15-6) Fuberidazole 100261 Group (16) a pyrrole series compound selected from (b-16-1) Fludioxonil 20 (b- 16-2) Fluoroimide and (b-16-3) Fenpiclonil [0027] Group (17) an organophosphorus series compound selected from 25 (b-17-1) Fosetyl-aluminium (b-17-2) Edifenphos (EDDP) (b-17-3) Tolclofos-methyl (b-17-4) Iprobenfos (IBP) and (b-17-5) Pyrazophos 30 [00281 Group (18) a copper series compound selected from (b-18-1) Cupric hydroxide (Copper hydroxide) (b- 18-2) Copper 35 (b-18-3) Basic copper chloride (Copper oxychloride) (b- 18-4) Basic copper sulfate (Copper sulfate (tribasic)) - 11 (b-18-5) Oxine-copper (b- 18-6) Copper sulfate pentahydrate (b-18-7) Anhydrous copper sulfate (b- 18-8) Copper nonylphenolsulfonate (Copper nonylphenylsulfate) and 5 (b-18-9) Copper dodecylbenzene sulfate bis(ethylenediamine) complex salt (DBEDC) [00291 Group (19) an antibiotics selected from (b-19-1) Kasugamycin hydrochloride hydrate 10 (b-19-2) Validamycin (b-19-3) Polyoxins A to N (b-19-4) Blastcidin-S benzylamino benzene sulfonate (b-19-5) Streptomycin (b-19-6) Natamycin 15 (b-19-7) Mildiomycin and (b- 19-8) Oxytetracycline [0030] Group (20) an organic chlorine series compound selected from 20 (b-20-1) Chlorothalonil (TPN) (b-20-2) Phthalide and (b-20-3) Quintozene [00311 Group (21) 25 a triazolopyrimidine series compound selected from (b-21-1) 5-Chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo [I,5-a]pyrimidine (b-21-2) 5-Chloro-N-[(1S)-2,2,2-trifluoro-1-methylethyl]-6-(2,4,6-trifluorophenyl) [1,2,4]triazolo[ 1,5-a]pyrimidine 30 (b-21-3) 5-Chloro-N-[(1R)-1,2-dimethylpropyl]-6-(2,4,6-trifluorophenyl)[1,2,4]tri azolo[ 1,5-a]pyrimidine (b-21-4) 5-(Methoxymethyl)-6-octyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine and (b-21-5) 5-Ethyl-6-octyl[ 1,2,4]triazolo[ 1,5-a]pyrimidin-7-amine [0032] 35 Group (22) a benzoyl compound selected from - 12 (b-22- 1) Metrafenone and (b-22-2) 3-(2,3,4-Trimethoxy-6-methylbenzoyl)-5-chloro-2-methoxy-4-methylpyridine [0033] Group (23) 5 an ethylenediamine series compound selected from (b-23-1) Isopropyl ((1S)-2-methyl-1-{[(4-methylbenzoyl)amino]methyl}propyl) carbamate (b-23 -2) Isopropyl ((1 S)-2,2-dimethyl- 1- {[(4-methylbenzoyl)amino]methyl } propyl) carbamate 10 (b-23-3) Isopropyl ((1S)-1-{[(1-benzofuran-2-ylcarbonyl)amino]methyl}-2-methyl propyl)carbamate (b-23-4) 2,2,2-Trifluoroethyl ((1 S)-2-methyl- 1-{ [(4-methylbenzoyl)amino]methyl} propyl)carbamate (b-23-5) 2,2,2-Trifluoroethyl ((1 S)-2,2-dimethyl- 1- { [(4-methylbenzoyl)amino]methyl} 15 propyl)carbamate (b-23-6) 2,2,2-Trifluoroethyl ((IS)-1-{[(1-benzofuran-2-ylcarbonyl)amino]methyl}-2 methylpropyl)carbamate (b-23-7) 2,2,2-Trifluoroethyl { (1S)-I -methyl-2-[(4-methylbenzoyl)amino] ethyl) carbamate 20 (b-23 -8) Benzyl ((1 S)-2-methyl- 1- { [(4-methylbenzoyl)amino]methyl} propyl)carbamate and (b-23-9) Isopropyl ((1 R)-2,2,2-trifluoro- 1- {[(4-methylbenzoyl)amino]methyl} ethyl) carbamate [0034] 25 Group (24) an isoxazolidin series compound selected from (b-24-1) 3-[5-(4-Chloro phenyl)-2,3-dimethylisoxazolidin-3-yl]pyridine, (b-24-2) 3-[2,3-Dimethyl-5-(4-methylphenyl)isoxazolidin-3-yl]pyridine and (b-24-3) 3-[2-Isopropyl-3-methyl-5-(4-chlorophenyl)isoxazolidin-3-yl]pyridine 30 [0035] Group (25) a quinoline series compound selected from (b-25- 1) Quinoxyfen (b-25-2) [6-(1,1-Dimethylethyl)-8-fluoro-2,3-dimethylquinoline-4-yl] acetate and 35 (b-25-3) [6-(1,1-Dimethylethyl)-8-fluoro-2,3-dimethylquinoline-4-yl] methoxyacetate [0036] - 13 Group (26) a thiazolidine series compound selected from (b-26-1) (2Z)- { [2-fluoro-5-(trifluoromethyl)phenyl]thio} [3-(2-methoxyphenyl)- 1,3 thiazolidin-2-ylidene]acetonitrile and 5 (b-26-2) (2Z)-{[2-fluoro-5-(trifluoromethyl)phenyl]thio}[3-(2-methylphenyl)-1,3 thiazolidin-2-ylidene]acetonitrile 100371 Group (27) a pyrazolinone series compound selected from 10 (b-27-1) 1-[(2-Propenylthio)carbonyl]-2-(1 -methylethyl)-4-(2-methylphenyl)-5-amino 1 H-pyrazol-3-one (b-27-2) 1-[(Ethylthio)carbonyl]-2-(1-methylethyl)-4-(2-methylphenyl)-5-amino- IH pyrazol-3-one and (b-27-3) 1 -[(Ethylthio)carbonyl] -2-(1 -methylethyl)-4-(2,6-dichlorophenyl)-5-amino 15 1 H-pyrazol-3-one, and [00381 Group (28) other fungicides and mildewcides selected from (b-28-1) Hydroxyisoxazol (Hymexazol) 20 (b-28-2) Fluazinam (b-28-3) Diclomezine (b-28-4) Tricyclazole (b-28-5) Cymoxanil (b-28-6) Famoxadone 25 (b-28-7) Fenamidone (b-28-8) Chloropicrin (b-28-9) Thiadiazine (Milneb) (b-28-1 0) Proquinazid (b-28-1 1) Spiroxamine 30 (b-28-12) Fenpropidin (b-28-13) Dithianon (b-28-14) Pencycuron (b-28-15) Isoprothiolane (b-28-16) Probenazole 35 (b-28-17) Resveratrol (b-28-18) Triforine - 14 (b-28-19) Acibenzolar-S-methyl (b-28-20) Pyroquilon (b-28-21) Dinocap (b-28-22) Nickel bis(dimethyldithiocarbamate) 5 (b-28-23) Etridiazole (Echlomezol) (b-28-24) Oxadixyl (b-28-25) Amobam (b-28-26) Pyrifenox (b-28-27) Oxolinic acid 10 (b-28-28) Phosphorous acid (b-28-29) Dazomet (b-28-30) Methyl isothiocyanate (b-28-3 1) Methasulfocarb (b-28-32) 1,3-dichloropropene 15 (b-28-33) Carbam (Metam) (b-28-34) Methyl iodide (Iodomethane) (b-28-35) Sulfur (b-28-36) Lime-sulfur mixed agent (Calcium polysulfide) (b-28-37) Fentin 20 (b-28-38) Sodium hypochlorite (b-28-39) Chinomethionat (b-28-40) Chloroneb (b-28-41) Anilazine (b-28-42) Nitrothal-isopropyl 25 (b-28-43) Fenitropan (b-28-44) Dicloran and (b-28-45) Benthiazole (2-(thiocyanatomethylthio)benzothiazole: TCMTB) as effective ingredients. Incidentally, in Compound (I), when m is 0, Ym represents a hydrogen atom, and 30 when n is 0, Xn represents a hydrogen atom. [0038a] In another aspect the present invention is a plant disease control composition comprising (Group a) (a) at least one kind of a quinoline compound selected from the group consisting of - 14a (a-14) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline, (a-18) 3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline, and (a-20) 3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline, or a salt thereof, and 5 (Group b) (b) one or more fungicides selected from the group consisting of the following Groups: Group (3) an imidazole series compound selected from (b-3-7) Triazoxide 10 Group (4) a carboxamide series compound selected from (b-4-7) Tecloftalam (b-4-8) Mandipropamid (b-4-13) Silthiofam 15 (b-4-15) Flumetover (b-4-17) Zoxamide (b-4-18) Tiadinil (b-4-19) Isotianil (b-4-20) Diclocymet 20 (b-4-21) Fenoxanil (b-4-22) Fluopicolide (b-4-24) Carpropamid (b-4-25) Tolfenpyrad (b-4-26) N-[2-(1,3-dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazol-4-carboxamide 25 (b-4-27) N-12-[1,1'-bi(cyclopropyl)-2-yl]phenyl}-3-(difluoromethyl)-1-methyl-1H-pyrazol-4 carboxamide (b-4-28) 3-(difluoromethyl)-N-(9-isopropyl-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl) 1-methyl-1 H-pyrazol-4-carboxamide (b-4-29) 3-(difluoromethyl)-N-[4'-(3,3-dimethylbutyn-1-yl)biphenyl-2-yl]-1-methyl-1H 30 pyrazol-4-carboxamide (b-4-30) 3-(difluoromethyl)-N-[4'-(3-methoxy-3-methylbutyn-1-yl)biphenyl-2-yl]-1-methyl 1H-pyrazol-4-carboxamide and (b-4-31) 3-(difluoromethyl)-1-methyl-N-[1,2,3,4-tetrahydro-9-(1-methylethyl)-1,4 methanonaphthalen-5-yl]-1H-pyrazol-4-carboxamide - 14b Group (5) an acylalanine series compound selected from (b-5-5) Furalaxyl-M Group (7) 5 a sulfoneamide series compound selected from (b-7-3) Flusulfamide Group (8) a sulfenamide series compound selected from (b-8-1) Tolylfluanid and 10 (b-8-2) Dichlofluanid Group (9) a carbamate series compound selected from (b-9-4) Pyribencarb Group (10) 15 a dithiocarbamate series compound selected from (b-10-8) Polycarbamate Group (12) a guanidine series compound selected from (b-12-4) Dodine 20 Group (13) a pyrimidine series compound selected from (b- 13-7) Dimethirimol (b-13-8) Bupirimate and (b-13-9) Diflumetorim 25 Group (14) a morpholine series compound selected from (b-14-2) Fenpropimorph (b- 14-3) Tridemorph (b- 14-4) Dodemorph and 30 Group (16) a pyrrole series compound selected from (b-16-2) Fluoroimide and Group (17) an organophosphorous series compound selected from - 14c (b-17-2) Edifenphos (b-17-3) Tolclofos-methyl (b-17-4) Iprobenfos and (b-17-5) Pyrazophos 5 Group (19) an antibiotics selected from (b-19-4) Blastcidin-S benzylamino benzenesulfonate (b-19-5) Streptomycin (b- 19-6) Natamycin 10 (b- 19-7) Mildiomycin and (b-19-8) Oxytetracycline Group (20) an organic chlorine series compound selected from (b-20-3) Quintozene 15 Group (21) a triazolopyrimidine series compound selected from (b-21-1) 5-Chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5 a]pyrimidine (b-21-2) 5-Chloro-N-[(1S)-2,2,2-trifluoro-1-methylethyl]-6-(2,4,6-trifluorophenyl) 20 [1,2,4]triazolo[1,5-a]pyrimidine (b-21-3) 5-Chloro-N-[(1R)-1,2-dimethylpropyl]-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5 a]pyrimidine (b-21-4) 5-(Methoxymethyl)-6-octyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine and (b-21-5) 5-Ethyl-6-octyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine 25 Group (22) a benzoyl compound selected from (b-22-1) Metrafenone and (b-22-2) 3-(2,3,4-Trimethoxy-6-methylbenzoyl)-5-chloro-2-methoxy-4-methylpyridine Group (24) 30 an isoxazolidin series compound selected from (b-24-1) 3-[5-(4-Chloro phenyl)-2,3-dimethylisoxazolidin-3-yl]pyridine (b-24-2) 3-[2,3-Dimethyl-5-(4-methylphenyl)isoxazolidin-3-yl]pyridine and (b-24-3) 3-[2-Isopropyl-3-methyl-5-(4-chlorophenyl)isoxazolidin-3-yl]pyridine Group (25) - 14d a quinoline series compound selected from (b-25-1) Quinoxyfen (b-25-2) [6-(1,1-Dimethylethyl)-8-fluoro-2,3-dimethyl quinoline-4-yl] acetate and (b-25-3) [6-(1,1-Dimethylethyl)-8-fluoro-2,3-dimethyl quinoline-4-yl] methoxyacetate 5 Group (26) a thiazolidine series compound selected from (b-26-1) (2Z)-{[2-fluoro-5-(trifluoromethyl)phenyl]thio}[3-(2-methoxy phenyl)-1,3 thiazolidin-2-ylidene]acetonitrile and (b-26-2) (2Z)-{[2-fluoro-5-(trifluoromethyl)phenyl]thio}[3-(2-methylphenyl)-1,3-thiazolidin 10 2-ylidene] acetonitrile Group (27) a pyrazolinone series compound selected from (b-27-1) 1- [(2-Propenylthio)carbonyl] -2- (1 -methylethyl)-4-(2-methylphenyl)-5 -amino-1H pyrazol-3-one 15 (b-27-2) 1- [(Ethylthio)carbonyl] -2- (1 -methylethyl)-4-(2-methylphenyl)-5 -amino-1 H-pyrazol 3-one and (b-27-3) 1- [(Ethylthio)carbonyl] -2- (1 -methylethyl)-4-(2,6-dichlorophenyl)-5 -amino-1H pyrazol-3-one and 20 Group (28) other fungicide- mildewcide selected from (b-28-1) Hydroxyisoxazol (b-28-7) Fenamidone (b-28-8) Chloropicrin 25 (b-28-9) Thiadiazine (b-28-10) Proquinazid (b-28-1 1) Spiroxamine (b-28-12) Fenpropidin (b-28-13) Dithianon 30 (b-28-14) Pencycuron (b-28-15) Isoprothiolane (b-28-16) Probenazole (b-28-17) Resveratrol (b-28-18) Triforine - 14e (b-28-19) Acibenzolar-S-methyl (b-28-20) Pyroquilon (b-28-21) Dinocap (b-28-22) Nickel bis(dimethyldithiocarbamate) 5 (b-28-23) Etridiazole (b-28-24) Oxadixyl (b-28-25) Amobam (b-28-26) Pyrifenox (b-28-27) Oxolinic acid 10 (b-28-28) Phosphorous acid (b-28-29) Dazomet (b-28-30) Methyl isothiocyanate (b-28-3 1) Methasulfocarb (b-28-32) 1,3-dichloropropene 15 (b-28-33) Carbam (b-28-34) Methyl iodide (b-28-35) Sulfur (b-28-36) Lime-sulfur mixed agent (b-28-37) Fentin 20 (b-28-38) Sodium hypochlorite (b-28-39) Chinomethionat (b-28-40) Chloroneb (b-28-41) Anilazine (b-28-42) Nitrothal-isopropyl 25 (b-28-43) Fenitropan (b-28-44) Dicloran and (b-28-45) Benthiazole as effective ingredients. 30 EFFECTS OF THE INVENTION [0039] The plant disease control composition of the present invention shows a broad spectrum against various plant pathogens (for example, rice blast (Pyricularia oryzae),gray mold (Botrytis cinerea) of tomato, cucumber and kidney bean, etc.) including fungi -15 and bacteria resistant to chemicals, and shows excellent controlling effects (synergistic controlling effects) which could never be expected from a single component alone. Also, it shows high plant disease controlling effects against existing fungi and bacteria resistant to chemicals, and no chemical damage against plants can be admitted. BEST MODE TO CARRY OUT THE INVENTION 00401 Respective terms used in Compound (1) in the claims and the specification of the present application mean, otherwise specifically mentioned, the definition generally 10 used in the field of chemistry and the definitions described in WO 2005/070917A, JP 20071 944A, WO 2007/01 1022A and JP 2007-217353A, In Compound (I) of the present invention, the C, to Ce alkyl portion of the "CI to C 6 alkyl group" or "C 1 to C 6 alkaneimidoyl group" can be a straight or branched alkyl group having I to 6 carbon atoms, for example, a methyl group, ethyl group, propyl 15 group, isopropyl group, butyl group, isobutyl group, s-butyi group, t-butyi group, pentyl group, isopentyl group, 2-methylbutyl group, neopentyl group, -ethylpropyl group, hexyl group, 4-methylpentyl group, 3-methylpentyl group, 2-rnmethylpentyl group, methylpentyl g group, 3,3-dimethyibutyl group, 2,2-dimethylbutyl group, Il-dimethyl butyl group, 1,2-dimethylbutyl group, 1,3-dimethylbutyl group, 2,3-dimethylbutyl 20 group, 2-ethylbutyl group, preferably a straight or branched alkyl group having I to 5 carbon atoms (C, to C, alkyl group), more preferably a straight or branched alkyl group having I to 4 carbon atoms (Ci to C 4 alkyl group), further more preferably a straight or branched alkyl group having to 3 carbon atoms (C: to C 3 alkyl group), particularly preferably a meithyl group, ethyl group or propyl group, most preferably a methyl group 25 or ethyl group. [0041] In Compound (I) of the present invention, the "C 2 to C 6 alkenyl group" may be either a straight t or branched, and can contain I or more optional number of double bondss, and there may be mentioned, for example, a vinyl group, prop-i -en-l-yl group, 30 allyl group, isopropenyl group, but-l-en-l-yI group, but-2-en-1-yl group, but-3-en-l-yl group, 2-methylprop-3-en-Ioup, group, I-methyiprop-3 -en--yl group, pent-I-en-I -yl group, pent-2-cn-I-yl group, pent-3-en-I-yl group, pent-4-en-I-yl group, 3-methylbut 2-en-l-yl group, 3-methylbut-3-en-i-yl group, hex-l-en-1-yl group, hex-2-en-I-yl group, hex-3-en-l-yl group, hex-4-en-1-yi group, hex-5-en-i-yl group or 4-methylpent 35 3-en- -yi group, preferably a vinyl group, allyl group, iso propenyl group or but-i-en-I yl group, more preferably an allyl group or isopropenyl group.
- 16 [00421 In Compound (I) of the present invention, the "C 2 to C 6 alkynyl group" may be either a straight or branched, and can contain 1 or more optional number of triple bond(s), and there may be mentioned, for example, an ethynyl group, prop-1-yn-1-yl 5 group, prop-2-yn-1-yl group, but-I-yn-1-yl group, but-3-yn-1-yl group, 1-methylprop-2 yn-l-yl group, pent-1-yn-1-yl group, pent-4-yn-1-yl group, hex-1-yn-1-yl group or hex 5-yn- I-yl group, preferably an ethynyl group or prop-i -yn- 1 -yl group. [00431 In Compound (I) of the present invention, the "aryl group" may be a C 6 to C 16 10 aromatic hydrocarbon group (6 to 16 carbon atoms), and there may be mentioned, for example, a phenyl group, 1 -naphthyl group, 2-naphthyl group, anthracenyl group, phenanthrenyl group, acenaphthylenyl group, etc., preferably a phenyl group, 1 naphthyl group or 2-naphthyl group, more preferably a phenyl group. [00441 15 In Compound (I) of the present invention, the "heteroaryl group" may be either a monocyclic or polycyclic, and may contain 1 or 2 or more same or different ring constituting hetero atom(s). A kind of said hetero atom(s) is not particularly limited, and may be mentioned, for example, a nitrogen atom, oxygen atom or sulfur atom. The heteroaryl group may be mentioned, for example, a 5- to 7-membered monocyclic 20 heteroaryl group such as a furyl group, thienyl group, pyrrolyl group, oxazolyl group, isoxazolyl group, dihydro isoxazolyl group, thiazolyl group, isothiazolyl group, imidazolyl group, pyrazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, tetrazolyl group, pyridyl group, azepinyl group, oxazepinyl group, etc., and the polycyclic heteroaryl group constituting the heteroaryl group may be a 8 to 14-mem 25 bered polycyclic heteroaryl group such as a benzofuranyl group, isobenzofuranyl group, benzothienyl group, indolyl group, isoindolyl group, indazolyl group, benzoxazolyl group, benzisoxazolyl group, benzothiazolyl group, benzisothiazolyl group, benzoxa diazolyl group, benzothiadiazolyl group, benzotriazolyl group, quinolyl group, iso quinolyl group, cinnolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl 30 group, naphthyridinyl group, purinyl group, pteridinyl group, carbazolyl group, carbolinyl group, acridinyl group, 2-acridinyl group, 3-acridinyl group, 4-acridinyl group, 9-acridinyl group, phenoxazinyl group, phenothiazinyl group, phenadinyl group, etc., preferably a furyl group, thienyl group, oxazolyl group, pyridyl group, benzo furanyl group or iso benzofuranyl group, more preferably a furyl group, thienyl group, 35 oxazolyl group or pyridyl group, particularly preferably a furyl group or thienyl group. [0045] - 17 In Compound (I) of the present invention, the "aralkyl group" is a group in which I or 2 or more hydrogen atom(s) (preferably 1 to 3 hydrogen atom(s), more preferablyl or 2 hydrogen atom(s)) of the above-mentioned "C 1 to C 6 alkyl group" is/are substituted by the above-mentioned "aryl group", and there may be mentioned, 5 for example, a benzyl group, 1 -naphthyl methyl group, 2-naphthyl methyl group, anthracenylmethyl group, phenanthrenylmethyl group, acenaphthylenylmethyl group, diphenylmethyl group, 1-phenethyl group, 2-phenethyl group, 1-(1-naphthyl)ethyl group, 1-(2-naphthyl)ethyl group, 2-(1-naphthyl)ethyl group, 2-(2-naphthyl)ethyl group, 3-phenylpropyl group, 3-(1-naphthyl)propyl group, 3-(2-naphthyl)propyl group, 4 10 phenylbutyl group, 4-(I-naphthyl)butyl group, 4-(2-naphthyl)butyl group, 5-phenyl pentyl group, 5-(1-naphthyl)pentyl group, 5-(2-naphthyl)pentyl group, 6-phenylhexyl group, 6-(1-naphthyl)hexyl group or 6-(2-naphthyl)hexyl group, preferably a benzyl group, diphenylmethyl group, 1 -phenethyl group or 2-phenethyl group, more preferably a benzyl group. 15 [0046] In Compound (I) of the present invention, the "C 3 to Cio cycloalkyl ring" is, for example, a cyclic hydrocarbon group in which an alkylene group having 2 to 9 carbon atoms such as an ethylene group, trimethylene group, tetramethylene group, penta methylene group, hexamethylene group, heptamethylene group, octamethylene group, 20 etc., is bonded to one carbon atom, preferably a cyclic hydrocarbon group (cyclobutyl ring, cyclopentyl ring or cyclohexyl ring) in which it is formed by bonding a trimethyl ene group, tetramethylene group or pentamethylene group, more preferably a cyclic hydrocarbon group (cyclohexyl ring) in which it is formed by bonding a pentamethyl ene group. 25 [0047] In Compound (I) of the present invention, "a halogen atom" is a fluorine atom, chlorine atom, bromine atom or iodine atom, preferably a fluorine atom, chlorine atom or bromine atom, more preferably a fluorine atom or chlorine atom, most preferably a fluorine atom. 30 [00481 In Compound (I) of the present invention, the "C to C 6 alkoxyl group" is a straight or branched alkoxyl group having 1 to 6 carbon atoms, for example, a methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, s-butoxy group, t-butoxy group, pentyloxy group, isopentyloxy group, 2-methylbutoxy 35 group, neopentyloxy group, 1-ethylpropoxy group, hexyloxy group, (4-methylpentyl) oxy group, (3-methylpentyl)oxy group, (2-methylpentyl)oxy group, (1-methylpentyl)- - 18 oxy group, 3,3-dimethylbutoxy group, 2,2-dimethylbutoxy group, 1,1-dimethylbutoxy group, 1,2-dimethylbutoxy group, 1,3-dimethylbutoxy group, 2,3-dimethylbutoxy group, 2-ethylbutoxy group, preferably a straight or branched alkoxyl group having 1 to 4 carbon atoms (C, to C 4 alkoxyl group), more preferably a methoxy group, ethoxy 5 group or isopropoxy group, further more preferably a methoxy group or ethoxy group, most preferably a methoxy group. In Compound (1) of the present invention, the "C to C 6 alkylthio group" is, for example, a straight or branched alkylthio group having 1 to 6 carbon atoms such as a methylthio group, ethylthio group, propylthio group, isopropylthio group, butylthio 10 group, isopentylthio group, neopentylthio group, 3,3-dimethylbutylthio group, 2-ethyl butylthio group, preferably a straight or branched alkylthio group having 1 to 4 carbon atoms, more preferably a methylthio group. [00491 In Compound (I) of the present invention, the "acyl group" may be mentioned, 15 for example, formyl group, a carbonyl group to which the above-mentioned "C to C 6 alkyl group" is bound (C 2 to C 7 alkylcarbonyl group), a carbonyl group to which the above-mentioned "C 2 to C 6 alkenyl group" is bound (C 3 to C 7 alkenylcarbonyl group), a carbonyl group to which the above-mentioned "aryl group" is bound ("arylcarbonyl group"), a carbonyl group to which the above-mentioned "C to C 6 alkoxyl group" is 20 bound (C 2 to C 7 alkoxycarbonyl group) or a carbonyl group to which the above mentioned "C 1 to C 6 alkylthio group" is bound (C 2 to C 7 alkylthio carbonyl group), preferably a formyl group, C 2 to C 5 alkylcarbonyl group, C 3 to C 5 alkenyl carbonyl group, benzoyl group, naphthoyl group, C 2 to Cs alkoxycarbonyl group or C 2 to C 5 alkylthio carbonyl group, more preferably a formyl group, C 2 to Cs alkylcarbonyl group, 25 benzoyl group or C 2 to C 5 alkoxycarbonyl group, particularly preferably an acetyl group, methoxycarbonyl group, ethoxycarbonyl group or benzoyl group, most preferably an acetyl group. [00501 In Compound (I) of the present invention, the "C 2 to C 7 alkoxycarbonyl group" 30 may be mentioned, for example, an alkoxycarbonyl group having 2 to 7 carbon atoms and the alkoxy portion may be straight or branched such as a methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, etc., preferably an alkoxycarbonyl group having 2 to 4 carbon atoms, more preferably a methoxycarbonyl group. [00511 35 In Compound (I) of the present invention, the "C to C 6 alkyl group which may be substituted by the same or different 1 to 3 halogen atom(s)" is, in addition to the - 19 above-mentioned "C to C 6 alkyl group", there may be mentioned, for example, the above-mentioned "C 1 to C 6 alkyl group" substituted by the same or different 1 to 3 "halogen atom(s)" mentioned above such as a trifluoromethyl group, trichloromethyl group, difluoromethyl group, dichloromethyl group, dibromomethyl group, fluoro 5 methyl group, chloromethyl group, bromomethyl group, iodomethyl group, 2,2,2 trichloroethyl group, 2,2,2-trifluoroethyl group, 2-bromoethyl group, 2-chloroethyl group, 2-fluoroethyl group, 3-chloropropyl group, 3,3,3-trifluoropropyl group, 4 fluorobutyl group, 3-fluoro-2-methylpropyl group, 3,3,3-trifluoro-2-methylpropyl group, 6,6,6-trichlorohexyl group, etc., preferably the above-mentioned "C 1 to C 4 alkyl 10 group" which may be substituted by the same or different 1 to 3 "halogen atom(s)" mentioned above, more preferably the above-mentioned "CI to C 3 alkyl group" which may be substituted by the same or different 1 to 3 "fluorine atom(s) or chlorine atom(s)", further more preferably a methyl group, ethyl group, propyl group, chloromethyl group or trifluoromethyl group, particularly preferably a methyl group, 15 ethyl group or trifluoromethyl group. [0052] In Compound (I) of the present invention, the "N-hydroxy C, to C 6 alkane imidoyl group the hydrogen atom of the hydroxyl group of which may be substituted by the substituent(s) selected from the group consisting of a C 1 to C 6 alkyl group, C 2 to C 6 20 alkenyl group, C 2 to C 6 alkynyl group, aralkyl group, aryl group and heteroaryl group" may be mentioned, for example, an N-hydroxyalkaneimidoyl group having 1 to 6 carbon atoms such as a hydroxyiminomethyl group, N-hydroxyethaneimidoyl group, N hydroxypropaneimidoyl group and N-hydroxybutaneimidoyl group, and in addition to the above, a group wherein the hydroxyl group of which is substituted by the above 25 mentioned "C 1 to C 6 alkyl group", the above-mentioned "C 2 to C 6 alkenyl group", the above-mentioned "C 2 to C 6 alkynyl group", the above-mentioned "aralkyl group", the above-mentioned "aryl group" or the above-mentioned "heteroaryl group", which can be, for example, a methoxyiminomethyl group, N-methoxyethaneimidoyl group, N ethoxyethaneimidoyl group, N-butoxyethaneimidoyl group, N-allyloxyethaneimidoyl 30 group, N-propargyloxyethaneimidoyl group, N-benzyloxyethaneimidoyl group, N phenoxyethaneimidoyl group, N-pyridyloxyethaneimidoyl group, N-methoxy propaneimidoyl group, N-methoxybutaneimidoyl group or N-methoxyhexaneimidoyl group, preferably an N-hydroxyalkaneimidoyl group having I to 4 carbon atoms in which the hydrogen atom(s) of the hydroxyl group(s) of which may be substituted by a 35 substituent(s) selected from the group consisting of a C 1 to C 6 alkyl group and phenyl group, more preferably a hydroxyiminomethyl group, N-hydroxyethaneimidoyl group, - 20 methoxyiminomethyl group, N-methoxyethaneimidoyl group or N-ethoxyethaneimidoyl group, particularly preferably a methoxyiminomethyl group or N-methoxyethane imidoyl group. 100531 5 In Compound (I) of the present invention, "the C, to C 6 alkyl group which may be substituted by the same or different I to 3 substituent(s) selected from the group consisting of a halogen atom, C to C 6 alkoxyl group, Ci to C 6 alkylthio group and phenoxy group" of R', etc., may include, in addition to the above-mentioned "C 1 to C 6 alkyl group which may be substituted by the same or different 1 to 3 halogen atom(s)", 10 for example, the above-mentioned "C 1 to C 6 alkyl group" substituted by the same or different 1 to 3 "Cl to C 6 alkoxyl group(s)" mentioned above such as a methoxymethyl group, ethoxymethyl group, ethoxyethyl group, propoxymethyl group, etc., the above mentioned "C 1 to C 6 alkyl group" substituted by the same or different I to 3 "C to C 6 alkylthio group(s)" mentioned above such as a methylthio methyl group, ethylthio 15 methyl group, ethylthioethyl group, etc., or the above-mentioned "C 1 to C 6 alkyl group" substituted by the phenoxy group such as a phenoxymethyl group, phenoxyethyl group, etc., and further include the above-mentioned "C 1 to C 6 alkyl group" substituted by 2 or 3 kinds of the substituents selected from the group consisting of the above-mentioned halogen atom, the above-mentioned Ci to C 6 alkoxyl group, the above-mentioned Ci to 20 C 6 alkylthio group and phenoxy group, such as a 2-methoxy-1-chloroethyl group, 3 phenoxy-2-bromo-2-methoxypropyl group, 3-phenoxy-2-bromo-2-methylthiopropy group, etc., preferably a methyl group, ethyl group, propyl group, methoxymethyl group, ethoxymethyl group, phenoxymethyl group or methylthiomethyl group, more preferably a methyl group or ethyl group. 25 [0054] In Compound (I) of the present invention, "the C, to C 6 alkyl group which may be substituted by the same or different 1 to 3 substituent(s) selected from the group consisting of a halogen atom, C to C 6 alkoxyl group, hydroxyl group, C 2 to C 7 alkoxy carbonyl group and phenoxy group" of X, etc., may include, in addition to the above 30 mentioned "C 1 to C 6 alkyl group which may be substituted by the same or different 1 to 3 halogen atom(s)", for example, the above-mentioned "C 1 to C 6 alkyl group" substi tuted by the same or different 1 to 3 "C to C 6 alkoxyl group(s)" mentioned above such as a methoxymethyl group, ethoxymethyl group, ethoxyethyl group, propoxymethyl group, etc., the above-mentioned "C to C 6 alkyl group" substituted by I to 3 hydroxyl 35 group(s) such as a hydroxymethyl group, 2-hydroxyethyl group, 3-hydroxypropyl group, etc., the above-mentioned "C 1 to C 6 alkyl group" substituted by the same or - 21 different I to 3 "C 2 to C 7 alkoxycarbonyl group(s)" mentioned above such as a methoxycarbonylmethyl group, ethoxycarbonylmethyl group, 2-(methoxycarbonyl) ethyl group, etc., or the above-mentioned "C 1 to C 6 alkyl group" substituted by a phenoxy group(s) such as a phenoxymethyl group, phenoxyethyl group, etc., and further 5 include the above-mentioned "C 1 to C 6 alkyl group" substituted by 2 or 3 kinds of substituents selected from the group consisting of the above-mentioned halogen atom, the above-mentioned Ci to C 6 alkoxyl group, hydroxyl group, the above-mentioned C 2 to C 7 alkoxycarbonyl group and phenoxy group such as a 2-methoxy- 1 -chloroethyl group, 2-hydroxy-1-chloroethyl group, 3-phenoxy-2-bromo-2-methoxycarbonylpropy 10 group, etc., preferably a methyl group, ethyl group, propyl group, methoxymethyl group, ethoxymethyl group, phenoxymethyl group, methylthiomethyl group, methoxy carbonylmethyl group or ethoxycarbonylmethyl group, more preferably a methyl group or ethyl group. [0055] 15 In Compound (I) of the present invention, "the C 2 to C 6 alkenyl group which may be substituted by the same or different 1 to 3 substituent(s) selected from the group consisting of a halogen atom, C 1 to C 6 alkoxyl group, C 2 to C7 alkoxycarbonyl group and phenoxy group" of X, etc., may include, in addition to the above-mentioned "C 2 to
C
6 alkenyl group", for example, the above-mentioned "C 2 to C 6 alkenyl group" substi 20 tuted by the same or different 1 to 3 halogen atom(s) such as a 3-chloroallyl group, 4 bromo-2-butenyl group, etc., the above-mentioned "C 2 to C 6 alkenyl group" substituted by the same or different I to 3 "C 1 to C 6 alkoxyl group(s)" mentioned above such as a 3-methoxy-2-propenyl group, 4-ethoxy-3-butenyl group, etc., the above-mentioned "C 2 to C 6 alkenyl group" substituted by the same or different 1 to 3 "C 2 to C7 alkoxycarbon 25 yl group(s)" mentioned above such as a methoxycarbonylvinyl group, 3-(ethoxycarbon yl)-2-propenyl group, 4-(methoxycarbonyl)-2-butenyl group, etc., or the above-men tioned "C 2 to C 6 alkenyl group" substituted by a phenoxy group such as a 3-phenoxy-2 butenyl group, etc., and further include the above-mentioned "C 2 to C 6 alkenyl group" substituted by 2 or 3 kinds of substituents selected from the group consisting of the 30 above-mentioned halogen atom, the above-mentioned C 1 to C 6 alkoxyl group, the above-mentioned C 2 to C7 alkoxycarbonyl group and the phenoxy group such as a 4 methoxy-3-chloro-2-butenyl group, 4-methoxycarbonyl-3-chloro-2-buteny group, 4 phenoxy-3-chloro-2-butenyl group, etc., preferably a vinyl group, allyl group, isopropenyl group, but-1-en-1-yl group, 3-chloroallyl group, 4-bromo-2-butenyl group, 35 methoxycarbonylvinyl group or 4-methoxycarbonylbutenyl group, more preferably an allyl group or isopropenyl group.
- 22 [00561 In Compound (I) of the present invention, "the C 2 to C 6 alkynyl group which may be substituted by the same or different I to 3 substituent(s) selected from the group consisting of a halogen atom, Ci to C 6 alkoxyl group and phenoxy group" of X, etc., 5 may include, in addition to the above-mentioned "C 2 to C 6 alkynyl group", for example, the above-mentioned "C 2 to C 6 alkynyl group" substituted by the same or different 1 to 3 halogen atom(s) such as a 3-chloro-2-propynyl group, 4-bromo-2-butynyl group, etc., the above-mentioned "C 2 to C 6 alkynyl group" substituted by the same or different 1 to 3 "Ci to C 6 alkoxyl group(s)" mentioned above such as a 3-methoxy-2-propynyl group, 10 4-ethoxy-3-butynyl group, etc., or the above-mentioned "C 2 to C 6 alkynyl group" substituted by a phenoxy group such as a 3-phenoxy-2-butynyl group, etc., and further include the above-mentioned "C 2 to C 6 alkynyl group" substituted by 2 or 3 kinds of substituents selected from the group consisting of the above-mentioned halogen atom, the above-mentioned C, to C 6 alkoxyl group and the phenoxy group such as a 4 15 methoxy-4-chloro-2-butynyl group, 4-phenoxy-4-chloro-2-butynyl group, etc., prefer ably an ethynyl group, prop-1-yn-1-yl group, 3-chloro-2-propynyl group, 3-methoxy-2 propynyl group, 4-methoxy-4-chloro-2-butynyl group or 4-phenoxy-4-chloro-2-butynyl group, preferably an ethynyl group or prop-1-yn-1-yl group. [00571 20 In Compound (I) of the present invention, "the amino group which may be substituted by the same or different 1 or 2 C 1 to C 6 alkyl group(s) or acyl group(s)" of X, etc., may include, in addition to the amino group, the amino group substituted by the same or different I or 2 "C 1 to C 6 alkyl group(s)" mentioned above or by the same or different I or 2 "acyl group(s)" mentioned above, preferably the amino group substi 25 tuted by the same or different 1 or 2 "C 1 to C 4 alkyl group(s)" mentioned above or the same or different 1 or 2 "acyl group(s)" mentioned above, more preferably a dimethyl amino group, diethylamino group or acetylamino group. (00581 In Compound (I) of the present invention, "the C 1 to C 6 alkylidene group" 30 formed by R 3 and R4 in combination, etc., may include, for example, a straight or branched alkylidene group having 1 to 6 carbon atoms such as a methylidene group (methylene group), ethylidene group, propylidene group, isopropylidene group, preferably a straight or branched alkylidene group having 1 to 4 carbon atoms, particularly preferably a methylidene group (methylene group). 35 [0059] In Compound (I) of the present invention, "an aryl group which may be - 23 substituted by the same or different 1 to 6 substituent(s) selected from the group consist ing of a halogen atom, C 1 to C 6 alkyl group which may be substituted by the same or different 1 to 3 halogen atom(s), C 1 to C 6 alkoxyl group, amino group which may be substituted by the same or different 1 or 2 C 1 to C 6 alkyl group(s) or acyl group(s), nitro 5 group, cyano group, hydroxyl group, mercapto group and C, to C 6 alkylthio group of
R
1 , etc., may include, in addition to the above-mentioned "aryl group", the above-men tioned "aryl group" substituted by the same or different 1 to 6 halogen atom(s) men tioned above, the above-mentioned "aryl group" substituted by the same or different 1 to 6 "C 1 to C 6 alkyl group(s) which may be substituted by the same or different I to 3 10 halogen atom(s)" mentioned above, the above-mentioned "aryl group" substituted by the same or different 1 to 6 "C 1 to C 6 alkoxyl group(s)" mentioned above, the above mentioned "aryl group" substituted by the same or different 1 to 6 "amino group(s) which may be substituted by the same or different 1 or 2 C, to C 6 alkyl group(s) or acyl group(s)" mentioned above, the above-mentioned "aryl group" substituted by 1 to 6 15 cyano group(s), the above-mentioned "aryl group" substituted by 1 to 6 hydroxyl group(s), the above-mentioned "aryl group" substituted by I to 6 mercapto group(s) or the above-mentioned "aryl group" substituted by the same or different 1 to 6 "C 1 to C 6 alkylthio group(s)" mentioned above, and further includes the above-mentioned "aryl group" substituted by 2 to 6 substituents selected from the above-mentioned halogen 20 atom, the above-mentioned "C 1 to C 6 alkyl group which may be substituted by the same or different I to 3 halogen atom(s)", the above-mentioned "C 1 to C 6 alkoxyl group", the above-mentioned "amino group which may be substituted by the same or different I or 2 C 1 to C 6 alkyl group(s) or acyl group(s)", nitro group, cyano group, hydroxyl group, mercapto group and the above-mentioned "C 1 to C 6 alkylthio group", preferably a 25 phenyl group, 1-naphthyl group, 2-naphthyl group, 4-fluorophenyl group, 4-chloro phenyl group, 3-methoxyphenyl group, 3-cyanophenyl group, 2-methylthiophenyl group or 2-trifluoromethylphenyl group, more preferably a phenyl group, 4-fluoro phenyl group or 4-chlorophenyl group. [0060] 30 In Compound (I) of the present invention, "a heteroaryl group which may be substituted by the same or different 1 to 6 substituent(s) selected from the group consisting of a halogen atom, C 1 to C 6 alkyl group which may be substituted by the same or different 1 to 3 halogen atom(s) and C 1 to C 6 alkoxyl group" of R 1 , etc., may include, in addition to the above-mentioned "heteroaryl group", for example, the above 35 mentioned "heteroaryl group" substituted by the same or different 1 to 6 halogen atom(s), the above-mentioned "heteroaryl group" substituted by the same or different 1 - 24 to 6 the above-mentioned "C 1 to C 6 alkyl group(s) which may be substituted by the same or different 1 to 3 halogen atom(s)" or the above-mentioned "heteroaryl group" substituted by the same or different 1 to 6 "C 1 to C 6 alkoxyl group(s)" mentioned above, further includes the above-mentioned "heteroaryl group" substituted by 2 to 6 kinds of 5 substituents selected from the group consisting of the above-mentioned halogen atom, the above-mentioned "C 1 to C 6 alkyl group" and the above-mentioned "C 1 to C 6 alkoxyl group", preferably a furyl group, thienyl group, oxazolyl group, pyridyl group, benzo furanyl group, isobenzofuranyl group, 5-bromofuryl group, 6-chloropyridyl group, 4 trifluoromethylpyridyl group, 3-fluorothienyl group or 3-methoxythienyl group, more 10 preferably a furyl group or thienyl group. [00611 In Compound (I) of the present invention, "the aralkyl group which may be substituted by the same or different 1 to 6 substituent(s) selected from the group consist ing of a halogen atom, a C 1 to C 6 alkyl group which may be substituted by the same or 15 different 1 to 3 halogen atom(s), a C 1 to C 6 alkoxyl group, an amino group which may be substituted by the same or different 1 or 2 C, to C 6 alkyl group(s) or acyl group(s), a nitro group, a cyano group, a hydroxyl group, a mercapto group and a C 1 to C 6 alkylthio group" of R', etc., may include, in addition to the above-mentioned "aralkyl group", the above-mentioned "aralkyl group" substituted by the same or different I to 6 halogen 20 atom(s), the above-mentioned "aralkyl group" substituted by the same or different 1 to 6 "Ci to C 6 alkyl group(s) which may be substituted by the same or different 1 to 3 halogen atom(s)" mentioned above, the above-mentioned "aralkyl group" substituted by the same or different 1 to 6 "C 1 to C 6 alkoxyl group(s)" mentioned above, the above mentioned "aralkyl group" substituted by the same or different 1 to 6 "amino group(s) 25 which may be substituted by the same or different 1 or 2 C 1 to C 6 alkyl group(s) or acyl groupss" mentioned above, the above-mentioned "aralkyl group" substituted byl to 6 nitro group(s), the above-mentioned "aralkyl group" substituted by 1 to 6 cyano group(s), the above-mentioned "aralkyl group" substituted by 1 to 6 hydroxyl group(s), the above-mentioned "aralkyl group" substituted by 1 to 6 mercapto group(s) or the 30 above-mentioned "aralkyl group" substituted by the same or different 1 to 6 "Ci to C 6 alkylthio group(s)" mentioned above, further include the above-mentioned "aralkyl group" substituted by 2 or more substituents selected from the group consisting of the above-mentioned halogen atom, the above-mentioned "C 1 to C 6 alkyl group which may be substituted by the same or different 1 to 3 halogen atom(s)", the above-mentioned 35 "CI to C 6 alkoxyl group", the above-mentioned "amino group which may be substituted by the same or different I or 2 C 1 to C 6 alkyl group(s) or acyl group(s)", a nitro group, a - 25 cyano group, a hydroxyl group, a mercapto group and the above-mentioned "Ci to C 6 alkylthio group", and when the aralkyl group has a substituent(s), the said substituent(s) may be bonded to either of or both of the aryl ring or the alkyl group constituting the aralkyl group, preferably a benzyl group, diphenylmethyl group, 1 -phenethyl group, 2 5 phenethyl group, 4-chlorobenzyl group, 3-cyanobenzyl group or 4-methylthio-2 phenethyl group, more preferably a benzyl group. [00621 In Compound (I) of the present invention, "the C 3 to CIO cycloalkyl ring which may be substituted by the same or different 1 to 3 substituent(s) selected from the group 10 consisting of a halogen atom, a C 1 to C 6 alkyl group, a CI to C 6 alkoxyl group and a phenoxy group, which is formed in combination with the carbon atoms to which they are bonded" of R1 and R 2 , etc., may include, in addition to the above-mentioned "C 3 to CIO cycloalkyl ring", for example, the above-mentioned "C 3 to CIO cycloalkyl ring" substituted by the same or different 1 to 3 halogen atom(s), the above-mentioned "C 3 to 15 CIO cycloalkyl ring" substituted by the same or different 1 to 3 "Ci to C 6 alkyl group(s)" mentioned above, the above-mentioned "C 3 to CIO cycloalkyl ring" substituted by the same or different 1 to 3 "C to C 6 alkoxyl group(s)" mentioned above or the above mentioned "C 3 to CIO cycloalkyl ring" substituted by the same or different 1 to 3 phenoxy group(s), further include the above-mentioned "C 3 to C 1 0 cycloalkyl ring" 20 substituted by 2 to 3 kinds of substituents selected from the group consisting of the above-mentioned halogen atom, the above-mentioned "C 1 to C 6 alkyl group", the above-mentioned "C 1 to C 6 alkoxyl group" and phenoxy group, preferably a cyclobutyl ring, cyclopentyl ring, cyclohexyl ring, 2-chlorocyclopentyl ring, 4-methylcyclohexyl ring, 3-methoxycyclohexyl ring or 3-phenoxycyclohexyl ring, more preferably a 25 cyclohexyl ring. [00631 In Compound (I) of the present invention, X can be substituted to an optional substitutable position(s) on the isoquinoline ring with I to 4 positions, and when Xs exist 2 to 4 (when n is 2 or more), these may be the same or different from each other. 30 [00641 In Compound (I) of the present invention, Y can be substituted to an optional substitutable position(s) on the quinoline ring with 1 to 6 positions, and when Ys exist 2 to 6 (when m is 2 or more), these may be the same or different from each other. [00651 35 Compound (I) in the present invention may be made, for example, a mineral acid salt such as a hydrochloride, sulfate, nitrate, etc.: a phosphate; a sulfonate such as a -26 methanesulfonate, ethanesulfonate, benzenesulfonate, p-tolusulfulfonate, etc.; or an organic carboxylate such as an acetate, benzoate, oxalate, fumarate, salicylate, etc. (preferably a hydrochloride, sulfate, nitrate, methanesulfonate, oxalate, fumarate or saicylate). 5 [0066] Compound (I) and a salt thereof of the present invention may be made a solvate, and these solvates are also contained in the present inventon. Such a solvate is preferably a hydrate. [0067] 10 In Compound (I) of the present invention, there is compound having an asymmetric carbon, and in such a case, the present nvention includes a kind of an optical isomer and a mixture of several kinds of optical isomers with an optional ratio. [0068] In Compound (I) of the present invention, 15 R, and R" are each (1a) preferably a Ci to C 6 alkyl group which may be substituted by the same or different I to 3 halogen atoms) or phenyl group which may be substituted by the same or different 1 to 5 halogen atom(s), (Ib) more preferably a methyl group, ethyl group, propyl group, trifluoromethyl group, 20 trifluoroethyl group, phenyl group, fluorophenyl group or chorophenyl group,
R
3 and R 4 are each (2a) preferably a hydrogen atom, a halogen atom or a C: to C4 alkyl group, (2b) more preferably a hydrogen atom, fluorine atom, chlorine atom, methyl group or ethyl group, 25 (2c) further rncre preferably a hydrogen atom, fluorine atom or methyl group, Xn are (3a) preferably X being a halogen atom; C; to C- alkyl group; C 2 to C 6 alkynyl group; aryl group which may be substituted by the same or different I to 6 substituent(s) selected from the group consisting of a halogen atom, CI to C, alkyl group which may 30 be substituted by the same or different I to 3 halogen atoms) and C, to C 6 alkoxyl group; heteroaryl group which may be substituted by the same or different I to 6 substituent(s) selected from the group consisting of a halogen atom, C0 to C& alkyl group which may be substituted by the same or different I to 3 halogen atoms) and C 1 to C 6 alkoxyl group; cyano group; or, N-hydroxy-CI to C 6 alkaneimidoyl group the 35 hydrogen atom of the hydroxyl group of which may be substituted by a substituent(s) selected from the group consisting ofa C 1 to C. alkyl group and phenyl group, and n is - 27 an integer of 0 to 2, (3b) more preferably X being a halogen atom; C 1 to C 4 alkyl group; C 2 to C 3 alkynyl group; phenyl group which may be substituted by the same or different I or 2 substi tuents selected from the group consisting of a fluorine atom, chlorine atom, C 1 to C 2 5 alkyl group which may be substituted by 1 to 3 fluorine atoms and C, to C 2 alkoxyl group; furyl group, thienyl group, oxazolyl group or pyridyl group each of which may be substituted by the same or different 1 to 3 substituent(s) selected from the group consisting of a fluorine atom, chlorine atom, C, to C 2 alkyl group which may be substituted by 1 to 3 fluorine atoms and C 1 to C 2 alkoxyl group; cyano group; or, N 10 hydroxy-C, to C 2 alkaneimidoyl group the hydrogen atom of the hydroxyl group of which may be substituted by a substituent selected from the group consisting of a C, to
C
2 alkyl group and phenyl group, and n is an integer of 0 to 2, (3c) further more preferably X being a fluorine atom, chlorine atom, bromine atom, methyl group, ethynyl group, furyl group, thienyl group, cyano group, methoxy 15 ethaneimidoyl group, ethoxyethaneimidoyl group or phenoxyethaneimidoyl group, and n is 0 or 1, Ym are (4a) preferably Y being a fluorine atom, chlorine atom, bromine atom or CI to C 3 alkyl group, and m is 0 to 2, 20 (4b) more preferably Y being a fluorine atom, chlorine atom or methyl group, and m is 0 or 1, (4c) further more preferably Y being a fluorine atom or methyl group, and m is 0 or 1. [00691 Also, a compound in which R' and R 2 are selected from (l a) to (Ib), R 3 and R 4 25 are selected from (2a) to (2c), Xn is selected from (3a) to (3c), Ym is selected from (4a) to (4c), and they are combined is suitable, and there may be mentioned, for example, (A1) a compound wherein R1 and R2 are each a C, to C 6 alkyl group which may be substituted by the same or different 1 to 3 halogen atom(s) or phenyl group which may be substituted by the same or different 1 to 5 halogen atom(s), 30 R 3 and R 4 are each a hydrogen atom, halogen atom or C to C 4 alkyl group, X is a halogen atom; C 1 to C 6 alkyl group; C 2 to C 6 alkynyl group; aryl group which may be substituted by the same or different 1 to 6 substituent(s) selected from the group consisting of a halogen atom, C to C 6 alkyl group which may be substituted by the same or different 1 to 3 halogen atom(s) and Ci to C 6 alkoxyl group; heteroaryl 35 group which may be substituted by the same or different 1 to 6 substituent(s) selected from the group consisting of a halogen atom, C 1 to C 6 alkyl group which may be - 28 substituted by the same or different 1 to 3 halogen atom(s) and C to C 6 alkoxyl group; cyano group; or, N-hydroxy-Ci to C 6 alkaneimidoyl group the hydrogen atom of the hydroxyl group of which may be substituted by a substituent selected from the group consisting of a C 1 to C 6 alkyl group and phenyl group, and n is an integer of 0 to 2, 5 Y is a fluorine atom, chlorine atom, bromine atom or C 1 to C 3 alkyl group, and m is 0 to 2, (A2) a compound wherein R1 and R2 are each a methyl group, ethyl group, propyl group, trifluoromethyl group, trifluoroethyl group, phenyl group, fluorophenyl group or chlorophenyl group, 10 R 3 and R 4 are each a hydrogen atom, fluorine atom, chlorine atom, methyl group or ethyl group, X is a halogen atom; C, to C 4 alkyl group; C 2 to C 3 alkynyl group; phenyl group which may be substituted by the same or different 1 or 2 substituents selected from the group consisting of a fluorine atom, chlorine atom, C to C 2 alkyl group which 15 may be substituted by 1 to 3 fluorine atoms and C to C 2 alkoxyl group; furyl group, thienyl group, oxazolyl group or pyridyl group each of which may be substituted by the same or different 1 to 3 substituent(s) selected from the group consisting of a fluorine atom, chlorine atom, C 1 to C 2 alkyl group which may be substituted by 1 to 3 fluorine atoms and C 1 to C 2 alkoxyl group; cyano group; or, N-hydroxy-Ci to C 2 alkaneimidoyl 20 group the hydrogen atom of the hydroxyl group of which may be substituted by a substituent(s) selected from the group consisting of a C, to C 2 alkyl group and phenyl group, and n is an integer of 0 to 2, Y is a fluorine atom, chlorine atom or methyl group, and m is 0 or 1, or (A3) a compound wherein R 1 and R 2 are each a methyl group, ethyl group, propyl 25 group, trifluoromethyl group, trifluoroethyl group, phenyl group, fluorophenyl group or chlorophenyl group,
R
3 and R 4 are each a hydrogen atom, fluorine atom or methyl group, X is a fluorine atom, chlorine atom, bromine atom, methyl group, ethynyl group, furyl group, thienyl group, cyano group, methoxyethaneimidoyl group, 30 ethoxyethaneimidoyl group or phenoxyethaneimidoyl group, and n is 0 or 1, Y is a fluorine atom or methyl group, and m is 0 or 1. [0070] Further preferred Compound (I) are (a-1) 3-(5-fluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline, 35 (a-2) 3-(5-chloro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline, (a-3) 3-(5-bromo-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline, - 29 (a-4) 3-(5-ethynyl-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline, (a-5) 3-(5,6-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline, (a-6) 3-(3-ethyl-5-fluoro-3-propyl-3,4-dihydroisoquinolin-1-yl)quinoline, (a-7) 3-(5-fluoro-3-methyl-3-propyl-3,4-dihydroisoquinolin-1-yl)quinoline, 5 (a-8) 3-(3-methyl-3-trifluoromethyl-3,4-dihydroisoquinolin-1-yl)quinoline (a-9) 3-[3-methyl-3-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-yl]quinoline, (a-10) 3-[3-methyl-3-phenyl-3,4-dihydroisoquinolin-1-yl]quinoline, (a-1) 3-[3-methyl-3-(4-fluorophenyl)-3,4-dihydroisoquinolin-1-yl]quinoline, (a-12) 3-[3-methyl-3-(4-chlorophenyl)-3,4-dihydroisoquinolin-1-yl]quinoline, 10 (a-13) 3-(3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline, (a-14) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline, (a-15) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)-6-fluoroquinoline, (a-16) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)-8-fluoroquinoline, (a-17) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)-8-methylquinoline, 15 (a-18) 3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline, (a-19) 3-(4,5-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline or (a-20) 3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline. [00711 The compounds (1: compound of Group a) in the present invention are known 20 compounds, and can be prepared by the methods, for example, described in WO 05/070917 pamphlet or in accordance with these methods. [0072] The compound in Group b of the present invention is selected from (B-1) preferably selected from 25 Group (1) a Strobilurin series compound selected from (b-I-1) Azoxystrobin (b- 1-2) Kresoxim-methyl (b-1-3) Pyraclostrobin 30 (b-1-4) Picoxystrobin (b-1 -5) Fluoxastrobin (b-1 -6) Dimoxystrobin (b-1 -7) Orysastrobin (b-1 -8) Metominostrobin and 35 (b-1-9) Trifloxystrobin, [0073] - 30 Group (2) a triazole series compound selected from (b-2-1) Simeconazole (b-2-2) Tebuconazole 5 (b-2-3) Fenbuconazole (b-2-4) Hexaconazole (b-2-5) Imibenconazole (b-2-6) Triadimefon (b-2-7) Tetraconazole 10 (b-2-8) Prothioconazole (b-2-9) Triticonazole (b-2-10) Epoxiconazole (b-2-1 1) Ipconazole (b-2-12) Metconazole 15 (b-2-13) Propiconazole (b-2-14) Cyproconazole (b-2-15) Difenoconazole (b-2-16) Diniconazole (b-2-17) Fluquinconazole 20 (b-2-18) Flusilazole (b-2-19) Penconazole (b-2-20) Bromuconazole (b-2-2 1) Triadimenol (b-2-22) Flutriafol 25 (b-2-23) Myclobutanil (b-2-24) Etaconazole and (b-2-25) Bitertanol, [00741 Group (3) 30 an imidazole series compound selected from (b-3-1) Oxpoconazole fumarate (b-3-2) Triflumizole (b-3-3) Imazalil (b-3-4) Imazalil-S 35 (b-3-5) Prochloraz (b-3-6) Pefurazoate and - 31 (b-3-7) Triazoxide, [0075] Group (4) a carboxamide series compound selected from 5 (b-4-1) Penthiopyrad (b-4-2) Flutolanil (b-4-3) Furametpyr (b-4-4) Boscalid (b-4-5) Fenhexamid 10 (b-4-6) Cyflufenamid (b-4-7) Tecloftalam (b-4-8) Mandipropamid (b-4-9) Bixafen (b-4-10) Carboxin 15 (b-4- 11) Oxycarboxin (b-4-12) Mepronil (b-4-13) Silthiofam (b-4-14) Thifluzamide (b-4-15) Flumetover 20 (b-4-16) Ethaboxam (b-4-17) Zoxamide (b-4-18) Tiadinil (b-4-19) Isotianil (b-4-20) Diclocymet 25 (b-4-21) Fenoxanil (b-4-22) Fluopicolide (b-4-23) Fluopyram (b-4-24) Carpropamid (b-4-25) Tolfenpyrad 30 (b-4-26) N-[2-(1,3-dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl-IH-pyrazol-4 carboxamide (b-4-27) N- {2-[ 1,1'-bi(cyclopropyl)-2-yl]phenyl} -3-(difluoromethyl)- 1-methyl-i H pyrazol-4-carboxamide (b-4-28) 3-(difluoromethyl)-N-(9-isopropyl-1,2,3,4-tetrahydro-1,4-methanonaphthalen 35 5-yl)-1 -methyl-I H-pyrazol-4-carboxamide (b-4-29) 3-(difluoromethyl)-N-[4'-(3,3-dimethylbutyn-1-yl)biphenyl-2-yl]-1-methyl- - 32 1 H-pyrazol-4-carboxamide (b-4-30) 3-(difluoromethyl)-N-[4'-(3-methoxy-3-methylbutyn-1-yl)biphenyl-2-yl]-1 methyl-I H-pyrazol-4-carboxamide and (b-4-31) 3 -(difluoromethyl)- 1 -methyl-N-[ 1,2,3,4-tetrahydro-9-(1 -methylethyl)- 1,4 5 methanonaphthalen-5-yl]-1H-pyrazol-4-carboxamide, [00761 Group (5) an acylalanine series compound selected from (b-5-1) Metalaxyl 10 (b-5-2) Metalaxyl-M (b-5-3) Benalaxyl (b-5-4) Benalaxyl-M and (b-5-5) Furalaxyl-M, [00771 15 Group (6) a valineamide series compound selected from (b-6-1) Benthiavalicarb-isopropyl and (b-6-2) Iprovalicarb; [0078] 20 Group (7) a sulfoneamide series compound selected from (b-7- 1) Cyazofamid (b-7-2) Amisulbrom and (b-7-3) Flusulfamide, 25 [00791 Group (8) a sulfenamide series compound selected from (b-8-1) Tolylfluanid and (b-8-2) Dichlofluanid, 30 [00801 Group (9) a carbamate series compound selected from (b-9- 1) Propamocarb (b-9-2) Propamocarb hydrochloride 35 (b-9-3) Diethofencarb and (b-9-4) Pyribencarb; -33 10081| Group (10) a dithiocarbam ate sees compound selected from (b-1O-I) Manzeb (Mancozeb) 5 (b-10-2) Maneb (b- 10-3) Propineb (b10-4) Zineb (b-10-5) Metiram (b 10-6) Zirar 10 (b-I0-7) Thiuram and b 10-B) Polycarbamate; 100821 Group (11) a dicarboxylimide series compound selected from 15 (b-I 1-1) liprodione (b- 1-2) Procymidone (- 1 n-3) Capto n (bM 1-4) Vinclo)zolin (b-I 1-5) Chlozolinate and 20 (bA 1-6) Folpet; 100831 Group (12) a guanidine series compound selected from (b- 12-1) Iminoctadine trialbesilate 25 (b-12-2) Iminoctadine-triacetate (b-12-3) Guazatine and (b-12-4) Dodie; 100841 Group (13) 30 a pyrimidine series compound selected from (b-13-1) Mepanipyrim (b-13-2) Fenarimol (b43-3) Ferimzone (b- 13-4) Cyprodinil 35 (b-13-5) Pyrimethani (b-3-6) Nuarimol - 34 (b-13-7) Dimethirimol (b-13-8) Bupirimate and (b-13-9) Diflumetorim; [00851 5 Group (14) a morpholine series compound selected from (b-14-1) Dimethomorph (b-14-2) Fenpropimorph (b-14-3) Tridemorph 10 (b- 14-4) Dodemorph and (b-14-5) Flumorph; [00861 Group (15) a benzimidazole series compound selected from 15 (b-15-1) Thiophanate (b- 15-2) Thiophanate-methyl (b-15-3) Benomyl (b- 15-4) Carbendazim (b-15-5) Thiabendazole and 20 (b-15-6) Fuberidazole, [00871 Group (16) a pyrrole series compound selected from (b-16-1) Fludioxonil 25 (b-16-2) Fluoroimide and (b-16-3) Fenpiclonil; 100881 Group (17) an organophosphorus series compound selected from 30 (b-17-1) Fosetyl-aluminium (b-17-2) Edifenphos (b-17-3) Tolclofos-methyl (b-17-4) Iprobenfos and (b-17-5) Pyrazophos, 35 [00891 Group (18) - 35 a copper series compound selected from (b-18-1) cupric hydroxide (b-18-2) copper (b- 18-3) basic copper chloride 5 (b-18-4) basic copper sulfate (b- 18-5) Oxine-copper (b- 18-6) copper sulfate pentahydrate (b- 18-7) anhydrous copper sulfate (b- 18-8) Copper nonylphenolsulfonate and 10 (b- 18-9) dodecyl benzene sulfonic acid bis ethylenediamine copper complex salt, [00901 Group (19) an antibiotics selected from (b-19-1) Kasugamycin hydrochloride hydrate 15 (b-19-2) Validamycin (b-19-3) Polyoxins A to N (b- 19-4) Blastcidin-S benzylamino benzene sulfonate (b- 19-5) Streptomycin (b-19-6) Natamycin 20 (b-19-7) Mildiomycin and (b-19-8) Oxytetracycline, [00911 Group (20) an organic chlorine series compound selected from 25 (b-20- 1) Chlorothalonil (b-20-2) Phthalide and (b-20-3) Quintozene, [00921 Group (21) 30 a triazolopyrimidine series compound selected from (b-21-1) 5-Chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo [1,5-a]pyrimidine (b-21-2) 5-Chloro-N-[(1 S)-2,2,2-trifluoro- 1 -methylethyl]-6-(2,4,6-trifluorophenyl) [1,2,4]triazolo[ 1,5-a]pyrimidine 35 (b-21-3) 5-Chloro-N-[(1 R)-1,2-dimethylpropyl]-6-(2,4,6-trifluorophenyl)[I,2,4]tri azolo[ 1,5-a]pyrimidine - 36 (b-21-4) 5-(Methoxymethyl)-6-octyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine and (b-21-5) 5-Ethyl-6-octyl[ 1,2,4]triazolo[ 1 ,5-a]pyrimidin-7-amine, [0093] Group (22) 5 a benzoyl compound selected from (b-22-1) Metrafenone and (b-22-2) 3-(2,3,4-Trimethoxy-6-methylbenzoyl)-5-chloro-2-methoxy-4-methyl pyridine, Group (23) an ethylene diamine series compound selected from 10 (b-23-1) Isopropyl ((IS)-2-methyl-1-{[(4-methylbenzoyl)amino]methyl}propyl) carbamate (b-23-2) Isopropyl ((1S)-2,2-dimethyl-1-{[(4-methylbenzoyl)amino]methyl}propyl) carbamate (b-23-3) Isopropyl ((1S)-1-{[(1-benzofuran-2-ylcarbonyl)amino]methyl}-2-methyl 15 propyl)carbamate (b-23-4) 2,2,2-Trifluoroethyl ((1S)-2-methyl-1-{[(4-methylbenzoyl)amino]methyl} propyl)carbamate (b-23-5) 2,2,2-Trifluoroethyl ((1 S)-2,2-dimethyl- 1- {[(4-methylbenzoyl)amino]methyl} propyl)carbamate 20 (b-23 -6) 2,2,2-Trifluoroethyl ((1 S)- 1- { [(1 -benzofuran-2-ylcarbonyl)amino]methyl} -2 methylpropyl)carbamate (b-23-7) 2,2,2-Trifluoroethyl { (1 S)- 1 -methyl-2-[(4-methylbenzoyl)amino] ethyl} carbanate (b-23-8) Benzyl ((IS)-2-methyl-1-{[(4-methylbenzoyl)amino]methyl}propyl)carbamate 25 and (b-23-9) Isopropyl ((1 R)-2,2,2-trifluoro- 1- { [(4-methylbenzoyl)amino]methyl} ethyl) carbamate, [00941 Group (24) 30 an isoxazolidin series compound selected from (b-24-1) 3-[5-(4-Chlorophenyl)-2,3-dimethylisoxazolidin-3-yl]pyridine and (b-24-2) 3-[2,3-Dimethyl-5-(4-methylphenyl)isoxazolidin-3-yl]pyridine and (b-24-3) 3-[2-Isopropyl-3-methyl-5-(4-chlorophenyl)isoxazolidin-3-yl]pyridine, [00951 35 Group (25) a quinoline series compound selected from - 37 (b-25- 1) Quinoxyfen (b-25-2) [6-(1,1 -Dimethylethyl)-8-fluoro-2,3-dimethylquinolin-4-yl] acetate and (b-25-3) [6-(1,1 -Dimethylethyl)-8-fluoro-2,3-dimethylquinolin-4-yl] methoxyacetate; 100961 5 Group (26) a thiazolidine series compound selected from (b-26-1) (2Z)-{[2-fluoro-5-(trifluoromethyl)phenyl]thio}[3-(2-methoxyphenyl)-1,3 thiazolidin-2-ylidene]acetonitrile and (b-26-2) (2Z)-{[2-fluoro-5-(trifluoromethyl)phenyl]thio}[3-(2-methylphenyl)-1,3 10 thiazolidin-2-ylidene]acetonitrile, [0097] Group (27) a pyrazolinone series compound selected from (b-27-1) 1 -[(2-Propenylthio)carbonyl]-2-(1 -methylethyl)-4-(2-methylphenyl)-5-amino 15 1H-pyrazol-3-one (b-27-2) I -[(Ethylthio)carbonyl] -2-(1 -methylethyl)-4-(2-methylphenyl)-5-amino- I H pyrazol-3-one and (b-27-3) 1- [(Ethylthio)carbonyl] -2-(1 -methylethyl)-4-(2,6-dichlorophenyl)-5-amino IH-pyrazol-3-one, and 20 [0098] Group (28) other fungicides and mildewcides selected from (b-28-1) Hydroxyisoxazol (b-28-2) Fluazinam 25 (b-28-3) Diclomezine (b-28-4) Tricyclazole (b-28-5) Cymoxanil (b-28-6) Famoxadone (b-28-7) Fenamidone 30 (b-28-8) Chloropicrin (b-28-9) Thiadiazine (b-28-10) Proquinazid (b-28-1 1) Spiroxamine (b-28-12) Fenpropidin 35 (b-28-13) Dithianon (b-28-14) Pencycuron - 38 (b-28-15) Isoprothiolane (b-28-16) Probenazole (b-28-17) Resveratrol (b-28-18) Triforine 5 (b-28-19) Acibenzolar-S-methyl (b-28-20) Pyroquilon (b-28-21) Dinocap (b-28-22) Nickel bis(dimethyl dithiocarbamate) (b-28-23) Etridiazole 10 (b-28-24) Oxadixyl (b-28-25) Amobam (b-28-26) Pyrifenox (b-28-27) Oxolinic acid and (b-28-28) Phosphorous acid 15 [00991 (B-2) further preferably selected from Group (1) a Strobilurin series compound selected from (b-I -1) Azoxystrobin 20 (b-1 -2) Kresoxim-methyl (b-1 -3) Pyraclostrobin (b-1 -4) Picoxystrobin (b-1-5) Fluoxastrobin (b-1 -6) Dimoxystrobin 25 (b-1 -7) Orysastrobin (b-1 -8) Metominostrobin and (b-1 -9) Trifloxystrobin, [0100] Group (2) 30 a triazole series compound selected from (b-2-1) Simeconazole (b-2-2) Tebuconazole (b-2-3) Fenbuconazole (b-2-4) Hexaconazole 35 (b-2-5) Imibenconazole (b-2-6) Triadimefon - 39 (b-2-7) Tetraconazole (b-2-8) Prothioconazole (b-2-9) Triticonazole (b-2- 10) Epoxiconazole 5 (b-2-1 1) Ipconazole (b-2-12) Metconazole (b-2-13) Propiconazole (b-2-14) Cyproconazole (b-2-15) Difenoconazole 10 (b-2-16) Diniconazole (b-2-17) Fluquinconazole and (b-2-18) Flusilazole [01011 Group (3) 15 an imidazole series compound selected from (b-3-1) Oxpoconazole fumarate (b-3-2) Triflumizole (b-3-3) Imazalil (b-3-4) Imazalil-S and 20 (b-3-5) Prochloraz [01021 Group (4) a carboxamide series compound selected from (b-4-1) Penthiopyrad 25 (b-4-2) Flutolanil (b-4-3) Furametpyr (b-4-4) Boscalid (b-4-5) Fenhexamid (b-4-6) Cyflufenamid 30 (b-4-7) Tecloftalam (b-4-8) Mandipropamid (b-4-9) Bixafen (b-4-10) Carboxin (b-4- 11) Oxycarboxin 35 (b-4-12) Mepronil (b-4-13) Silthiofam - 40 (b-4-14) Thifluzamide (b-4-15) Flumetover (b-4-16) Ethaboxam (b-4-17) Zoxamide 5 (b-4-18) Tiadinil (b-4-19) Isotianil (b-4-20) Diclocymet (b-4-21) Fenoxanil (b-4-22) Fluopicolide 10 (b-4-23) Fluopyram (b-4-24) Carpropamid (b-4-25) Tolfenpyrad (b-4-26) N-[2-(1,3-dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl-IH-pyrazol-4 carboxamide 15 (b-4-27) N- {2-[ 1,1'-bi(cyclopropyl)-2-yl]phenyl} -3-(difluoromethyl)- 1-methyl-I H pyrazol-4-carboxamide (b-4-28) 3-(Difluoromethyl)-N-(9-isopropyl-1,2,3,4-tetrahydro-1,4-methanonaphthalen 5-yl)-1 -methyl-i H-pyrazol-4-carboxamide (b-4-29) 3-(Difluoromethyl)-N-[4'-(3,3-dimethylbutyn-1-yl)biphenyl-2-yl)-1-methyl 20 1 H-pyrazol-4-carboxamide and (b-4-30) 3-(Difluoromethyl)-N-[4'-(3-methoxy-3-methylbutyn-1-yl)biphenyl-2-yl]-1 methyl-i H-pyrazol-4-carboxamide 10103] Group (5) 25 an acylalanine series compound selected from (b-5-1) Metalaxyl (b-5-2) Metalaxyl-M (b-5-3) Benalaxyl and (b-5-4) Benalaxyl-M 30 [0104] Group (6) a valineamide series compound selected from (b-6-1) Benthiavalicarb-isopropyl and (b-6-2) Iprovalicarb; 35 [0105] Group (7) - 41 a sulfoneamide series compound selected from (b ) Cyazofamid (b-7-2) Amisulbrom and (b-73) Flusulfainde, 5 10106 Group (8) a sulfenamide series compound selected from (b-S-I) Toiylfluanid and (b-8-2) DichloFluanid, 10 101071 Group (9) a carbamate series compound selected from (b -9- 1) Propamocarb (b-9-2) Propamocarb hydrochloride 15 (b-9-3) Diethoflencarb and (b-9-4) Pyribencarb; 10108 Group (10) a dithiocarbamate series compound selected from 20 (b-10-1) MIanzb (Mancozeb) (b-10-2) Maneb (b 10-3) Propineb (b-10-4) Zineb (b-10-5) Metim 25 (b-10-6) Ziram (b-10-7) Thiuram and (b-10-8) Polycarbamate; 10109] Group (11) 30 a dicarboxylimide series compound selected from (b-i 1-) Iprodione (b-1 -2) Procynidone (b- 1-3) Captan (b-I 1-4) Vinclozolin 35 (b- I 1-5) Chiozolinate and (b 16) Folpe:; - 42 [01101 Group (12) a guanidine series compound selected from (b-12-1) Iminoctadine trialbesilate 5 (b-12-2) hninoctadine-triacetate (b-12-3) Guazatine and (b-12-4) Dodine; [01111 Group (13) 10 a pyrimidine series compound selected from (b-13-1) Mepanipyrim (b-13-2) Fenarimol (b-I 3-3) Ferimzone (b-13-4) Cyprodinil and 15 (b-13-5) Pyrimethanil; [01121 Group (14) a morpholine series compound selected from (b-14-1) Dimethomorph 20 (b-14-2) Fenpropimorph (b-14-3) Tridemorph (b-I 4-4) Dodemorph and (b-1 4-5) Flumorph; [01131 25 Group (15) a benzimidazole series compound selected from (b-15-1) Thiophanate (b-15-2) Thiophanate-methyl (b-15-3) Benomyl 30 (b-15-4) Carbendazim (b-15-5) Thiabendazole and (b-15-6) Fuberidazole, [0114] Group (16) 35 a pyrrole series compound selected from (b-16-1) Fludioxonil - 43 (b-16-2) Fluoroimide and (b-16-3) Fenpiclonil; [01151 Group (17) 5 an organophosphorous series compound selected from (b-17-1) Fosetyl-aluminium (b-17-2) Edifenphos and (b-17-3) Tolclofos-methyl, [01161 10 Group (18) a copper series compound selected from (b-18-1) Cupric hydroxide (b-18-2) Copper (b-18-3) Basic copper chloride 15 (b-18-4) Basic copper sulfate (b-18-5) Oxine-copper (b-18-6) Copper sulfate pentahydrate and (b-18-7) Anhydrous copper sulfate, [01171 20 Group (19) an antibiotics selected from (b- 19-1) Kasugamycin hydrochloride hydrate (b-19-2) Validamycin (b-19-3) Polyoxins B and D 25 (b-19-4) Blastcidin-S benzylaminobenzene sulfonate, and (b-19-5) Streptomycin, [0118] Group (20) an organic chlorine series compound selected from 30 (b-20-1) Chlorothalonil (b-20-2) Phthalide and (b-20-3) Quintozene, [0119] Group (21) 35 a triazolopyrimidine series compound selected from (b-21-1) 5-Chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo- - 44 [1,5-a]pyrimidine (b-21-2) 5-Chloro-N-[(1S)-2,2,2-trifluoro-1-methylethyl]-6-(2,4,6-trifluorophenyl) [1,2,4]triazolo[ 1,5-a]pyrimidine (b-21-3) 5-Chloro-N-[(IR)-1,2-dimethylpropyl]-6-(2,4,6-trifluorophenyl)[1,2,4]tri 5 azolo[ l,5-a]pynmidine (b-21-4) 5-(Methoxymethyl)-6-octyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine and (b-21-5) 5-Ethyl-6-octyl[ 1,2,4]triazolo[ 1,5-a]pyrimidin-7-amine, [01201 Group (22) 10 a benzoyl compound selected from (b-22-1) Metrafenone and (b-22-2) 3-(2,3,4-Trimethoxy-6-methylbenzoyl)-5-chloro-2-methoxy-4-methylpyridine, [01211 Group (23) 15 an ethylenediamine series compound selected from (b-23 -1) Isopropyl ((1 S)-2-methyl- 1- { [(4-methylbenzoyl)amino]methyl } propyl) carbanate (b-23-2) Isopropyl ((1 S)-2,2-dimethyl- 1- {[(4-methylbenzoyl)amino]methyl} propyl) carbamate 20 (b-23-3) Isopropyl ((1S)-1-{[(1-benzofuran-2-ylcarbonyl)amino]methyl}-2-methyl propyl)carbamate (b-23-4) 2,2,2-Trifluoroethyl ((1S)-2-methyl-1-{[(4-methylbenzoyl)amino]methyl} propyl)carbamate (b-23-5) 2,2,2-Trifluoroethyl ((I S)-2,2-dimethyl-1-{[(4-methylbenzoyl)amino]methyl} 25 propyl)carbamate (b-23-6) 2,2,2-Trifluoroethyl ((1S)-1-{[(1-benzofuran-2-ylcarbonyl)amino]methyl}-2 methylpropyl)carbamate (b-23-7) 2,2,2-Trifluoroethyl ((1 S)- 1 -methyl-2-[(4-methylbenzoyl)amino] ethyl} carbamate 30 (b-23-8) Benzyl ((1S)-2-methyl-1-{[(4-methylbenzoyl)amino]methyl}propyl)carbamate and (b-23-9) Isopropyl ((1 R)-2,2,2-trifluoro- 1- { [(4-methylbenzoyl)amino]methyl } ethyl) carbanate, {01221 35 Group (24) an isoxazolidine series compound which is - 45 (b-24-1) 3-[5-(4-Chloro phenyl)-2,3-dimethylisoxazolidin-3-yl]pyridine; [0123] Group (25) a quinoline series compound selected from 5 (b-25-1) Quinoxyfen and (b-25-2) [6-(1,1-Dimethylethyl)-8-fluoro-2,3-dimethylquinoline-4-yl] acetate; [01241 Group (26) a thiazolidine series compound which is 10 (b-26-1) (2Z)-{[2-fluoro-5-(trifluoromethyl)phenyl]thio}[3-(2-methoxyphenyl)-1,3 thiazolidin-2-ylidene]acetonitrile, [0125] Group (27) a pyrazolinone series compound which is 15 (b-27-1) 1-[(2-Propenylthio)carbonyl]-2-(1-methylethyl)-4-(2-methylphenyl)-5-amino 1 H-pyrazol-3-one, and [0126] Group (28) other fungicides and mildewcides selected from 20 (b-28-1) Hydroxyisoxazol (b-28-2) Fluazinam (b-28-3) Diclomezine (b-28-4) Tricyclazole (b-28-5) Cymoxanil 25 (b-28-6) Famoxadone (b-28-7) Fenamidone (b-28-8) Chloropicrin (b-28-9) Thiadiazine (b-28-10) Proquinazid 30 (b-28-1 1) Spiroxamine (b-28-12) Fenpropidin (b-28-13) Dithianon (b-28-14) Pencycuron (b-28-15) Isoprothiolane 35 (b-28-16) Probenazole (b-28-17) Resveratrol - 46 (b-28-18) Triforine (b-28-19) Acibenzolar-S-methyl (b-28-20) Pyroquilon (b-28-21) Dinocap 5 (b-28-27) Oxolinic acid and (b-28-28) Phosphorous acid, 101271 (B-3) further more preferably selected from Group (1) 10 a Strobilurin series compound selected from (b-I-1) Azoxystrobin and (b-1-2) Kresoxim-methyl, [01281 Group (2) 15 a triazole series compound selected from (b-2-1) Simeconazole (b-2-2) Tebuconazole (b-2-3) Fenbuconazole (b-2-4) Hexaconazole 20 (b-2-5) Imibenconazole and (b-2-6) Triadimefon, 10129] Group (3) an imidazole series compound selected from 25 (b-3-1) Oxpoconazole fumarate and (b-3-2) Triflumizole, [01301 Group (4) a carboxamide series compound selected from 30 (b-4-1) Penthiopyrad (b-4-2) Flutolanil (b-4-3) Furametpyr (b-4-4) Boscalid (b-4-5) Fenhexamid 35 (b-4-6) Cyflufenamid and (b-4-7) Tecloftalam, - 47 101311 Group (5) an acylalanine series compound selected from (b-5-1) Metalaxy! (b-5-3) Benalaxyl and (b-5-4) Benalaxyl-M, [01321 Group (6) 10 a vaineamide eries compound which is (b-6-1) Benthiavallcarb-isopropyl, 101331 Group (7) a sulfoneamide series compound which is 15 (b-7- 1) Cyazofamid, 101341 Group (9) a cabamate series cmpound selected from (b-9-1 ) Propamocarb hydrochloride and 20 (b-9-2) Diethofencarb, [01351 Group (10) a dithiocarbamate series compound selected from (b-10-1) Manzeb (Mancozeb) and 25 (b- 10-2) Maneb, 101361 Group (11) a dicarboxylimide series compound selected from (b-I 1-1) Iprodione 30 (b- 11-2) Procymidone and (b- 11-3) Captan, 10137] Group (12) a guanidine series compound which is 35 (b-12-1) Iminoctadine trialbesilate, [0138] - 48 Group (13) a pyrimidine series compound selected from (b-13-1) Mepanipyrim (b-13-2) Fenarimol and 5 (b-13-3) Ferimzone, [01391 Group (14) a morpholine series compound which is (b-14-1) Dimethomorph, 10 [01401 Group (15) a benzimidazole series compound which is (b-15-I) Thiophanate-methyl, [01411 15 Group (16) a pyrrole series compound which is (b-16-1) Fludioxonil, [01421 Group (18) 20 a copper series compound which is (b-18-1) cupric hydroxide, [0143] Group (19) an antibiotics selected from 25 (b-19-1) Kasugamycin hydrochloride hydrate (b-19-2) Validamycin, and (b-19-3) Polyoxins B and D, [01441 Group (20) 30 an organic chlorine series compound selected from (b-20-1) Chlorothalonil and (b-20-2) Phthalide, [01451 Group (23) 35 an ethylenediamine series compound selected from (b-23- 1) Isopropyl ((1 S)-2-methyl- 1- { [(4-methylbenzoyl)amino]methyl)propyl)- - 49 carbamate (b-23-2) Isopropyl ((1S)-2,2-dimethyl-1-{[(4-methylbenzoyl)amino]methyl}propyl) carbamate (b-23-3) Isopropyl ((1 S)- 1- { [(1 -benzofuran-2-ylcarbonyl)amino]methyl} -2-methyl 5 propyl)carbamate (b-23-4) 2,2,2-Trifluoroethyl ((1 S)-2-methyl- 1- { [(4-methylbenzoyl)amino]methyl} propyl)carbamate (b-23-5) 2,2,2-Trifluoroethyl ((1 S)-2,2-dimethyl- 1- { [(4-methylbenzoyl)amino]methyl} propyl)carbamate 10 (b-23-6) 2,2,2-Trifluoroethyl ((1S)-1-{[(1-benzofuran-2-ylcarbonyl)amino]methyl}-2 methylpropyl)carbamate (b-23-7) 2,2,2-Trifluoroethyl {( S)- 1 -methyl-2-[(4-methylbenzoyl)amino]ethyl} carbamate (b-23-8) Benzyl ((1 S)-2-methyl- 1- { [(4-methylbenzoyl)amino] methyl} propyl)carbamate 15 and (b-23-9) Isopropyl ((1 R)-2,2,2-trifluoro- 1- { [(4-methylbenzoyl)amino]methyl} ethyl) carbamate, and 101461 Group (28) 20 other fungicides and mildewcides selected from (b-28-2) Fluazinam (b-28-3) Diclomezine (b-28-4) Tricyclazole (b-28-5) Cymoxanil and 25 (b-28-6) Famoxadone. [0147] The compounds of Group b in the present invention are known compounds, and they can be prepared by, for example, the methods described in The Pesticide Manual (14th Edition) [British Crop Protection Council Pubn., 2006], WO 97/15552A, 30 WO 03/070705A, AGROW No. 243 (1995), WO 99/024413A, WO 04/016088A, WO 03/010149A, WO 03/74491A, WO 04/35589A, WO 04/58723A, WO 99/21851A, WO 01/10825A, WO 98/46607A, JP 2000-119275A, WO 02/38565A, WO 06/87325A, WO 05/87773A, WO 02/02527A, WO 03/008372A, WO 05/042474A, WO 07/111024A, JP 2006-282508A, JP 2000-281678A, WO 01/92231A, JP 2000-319270A and JP 2000 35 226374A or in accordance with these methods. [01481 - 50 The plant disease control composition of the present invention gives synergistic controlling effects as compared to the case where each effective ingredient is used alone. [0149] 5 The plant disease control composition of the present invention may be used as such, but it is generally used by mixing with a carrier, and depending on necessity, by adding an auxiliary for preparation such as a surfactant, wetting agent, fixing agent, thickener, antiseptics, colorant, stabilizer, etc., to prepare a wettable powder, flowable, water dispersible granule, dust formulation, emulsifiable concentrate, etc., according to 10 the conventionally known method and used suitably. A content of the quinoline compound (I: compound of Group a) as an effective ingredient in these preparations is generally in the range of 0.005 to 99%, preferably in the range of 0.01 to 90%, more preferably in the range of 0.1 to 85% in a weight ratio. Also, a content of the fungicidal compound of Group b as an effective ingredient in these preparations is 15 generally in the range of 0.005 to 99%, preferably in the range of 0.1 to 90% in a weight ratio, and a sum of the quinoline compound (I: compound of Group a) and the fungicidal compound of Group b is generally in the range of 0.005 to 99%, preferably in the range of 0.01 to 90%, more preferably in the range of 0.1 to 85% in a weight ratio. A mixing ratio of the quinoline compound (1: compound of Group a) and the fungicidal 20 compound of Group b is generally 0.01 to 1000 of the fungicidal compound of Group b based on the quinoline compound as 1, preferably 0.1 to 100 of the fungicidal compound of Group b based on the quinoline compound as 1 in a weight ratio. 10150] In the plant disease control composition of the present invention, a total content 25 of the effective ingredients including the quinoline compound (I: compound of Group a) and the fungicidal compound of Group b may vary depending on the form of the preparation, and generally 0.01 to 30% by weight in the dust formulation, 0.1 to 80% by weight in the wettable powder, 0.5 to 20% by weight in the granule, 2 to 50% by weight in the emulsifiable concentrate, 1 to 50% by weight in the flowable preparation, and 1 to 30 80% by weight in the dry flowable preparation. It is preferably 0.05 to 10% by weight in the dust formulation, 5 to 60% by weight in the wettable powder, 5 to 20% by weight in the emulsifiable concentrate, 5 to 50% by weight in the flowable preparation, and 5 to 50% by weight in the dry flowable preparation. A content of the auxiliary is 0 to 80% by weight, and a content of the carrier is an amount in which total contents of the 35 compounds of the effective ingredients and the auxiliary are deducted from 100% by weight.
- 51 [01511 The carrier to be used in the above-mentioned composition means a synthetic or natural inorganic or organic substance to be formulated for the purposes of helping the effective ingredients to be reached to the portion to be treated, and making storage, 5 transport and handling of the compounds of effective ingredients easy. Either of the solid or liquid carriers may be used so long as it is generally used for agricultural and horticultural chemicals, and not limited to specific materials. The solid carrier may be mentioned, for example, inorganic substance substances such as bentonite, mont morillonite, kaolinite, diatomaceous earth, white clay, talc, clay, vermiculite, gypsum, 10 calcium carbonate, amorphous silica, ammonium sulfate, etc.; vegetable organic substances such as soybean powder, wood powder, sawdust, wheat powder, lactose, sucrose, glucose, etc.; or urea, etc. The liquid carrier may be mentioned, for example, aromatic hydrocarbons and naphthenes such as toluene, xylene, cumene, etc.; paraffin series hydrocarbons such as n-paraffin, iso-paraffin, liquid paraffin, kelosine, mineral 15 oil, polybutene, etc.; ketones such as acetone, methylethyl ketone, etc.; ethers such as dioxane, diethylene glycol dimethyl ether, etc.; alcohols such as ethanol, propanol, ethylene glycol, etc.; carbonates such as ethylene carbonate, propylene carbonate, butylene carbonate, etc.; aprotic solvents such as dimethylformamide, dimethylsulf oxide, etc.; or water, etc. 20 [0152] Further, to strengthen the effect of the compounds in the composition of the present invention, an auxiliary may be used each singly or in combination depending on the purposes and considering the preparation form of the preparation, treatment methods, etc. As the auxiliary, a surfactant which is generally used for the purpose of 25 emulsifying, dispersing, spreading or/and wetting the agricultural preparation may be mentioned, for example, a nonionic surfactant such as a sorbitane fatty acid ester, polyoxyethylene sorbitane fatty acid ester, sucrose fatty acid ester, polyoxyethylene fatty acid ester, polyoxyethylene resin acid ester, polyoxyethylene fatty acid diester, polyoxyethylene castor oil, polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl 30 ether, polyoxyethylene dialkyl phenyl ether, formalin condensate of polyoxyethylene alkyl phenyl ether, polyoxyethylene polyoxypropylene block polymer, alkyl polyoxy ethylene polyoxypropylene block polymer ether, alkyl phenyl polyoxyethylene poly oxypropylene block polymer ether, polyoxyethylene alkyl amine, polyoxyethylene fatty acidamide, polyoxyethylene bisphenyl ether, polyoxyalkylene benzyl phenyl ether, 35 polyoxyalkylene styrylphenyl ether, polyoxyalkylene adduct of a higher alcohol, and polyoxyethylene ether and ester type silicone and fluorine series surfactant, etc.; an - 52 anionic surfactant such as an alkyl sulfate, polyoxyethylene alkyl ether sulfate, poly oxyethylene alkyl phenyl ether sulfate, polyoxyethylene benzyl phenyl ether sulfate, polyoxyethylene styrylphenyl ether sulfate, polyoxyethylene polyoxypropylene block polymersulfate, paraffin sulfonate, alkanesulfonate, AOS, dialkyl sulfosuccinate, alkyl 5 benzene sulfonate, naphthalene sulfonate, dialkyl naphthalene sulfonate, formalin condensate of naphthalene sulfonate, alkyl diphenyl ether disulfonate, lignin sulfonate, polyoxyethylene alkyl phenyl ether sulfonate, polyoxyethylene alkyl ether sulfosuccinic acid half ester, fatty acid salt, N-methyl-fatty acid sarcosinate, resin acid salt, polyoxy ethylene alkyl ether phosphate, polyoxyethylene phenyl ether phosphate, polyoxyethyl 10 ene dialkylphenyl ether phosphate, polyoxyethylene benzylated phenyl ether phosphate, polyoxyethylene benzylated phenyl phenyl ether phosphate, polyoxyethylene styrylated phenyl ether phosphate, polyoxyethylene styrylated phenyl phenyl ether phosphate, polyoxyethylene polyoxypropylene block polymerphosphate, phosphatidylcholine, phosphatidylethanol imine, alkyl phosphate, sodium tripolyphosphate, etc.; a cationic 15 surfactant such as a polyanion type polymer surfactant derived from acrylic acid, acrylonitrile and acrylamido methylpropane sulfonic acid, alkyl trimethyl ammonium chloride, methyl polyoxyethylene alkyl ammonium chloride, alkyl N-methyl pyridinium bromide, monomethylated ammonium chloride, dialkyl methylated ammonium chloride, alkyl penta methylpropylene amine dichloride, alkyl dimethyl benzalkonium 20 chloride, benzethonium chloride, etc.; or an amphoteric surfactant such as a dialkyl diaminoethyl betaine, alkyl dimethyl benzyl betaine, etc. A binder to be used as the auxiliary may be mentioned, for example, sodium arginate, polyvinyl alcohol, Gum Arabic, CMC sodium or bentonite, etc., a disintegrator may be mentioned, for example, CMC sodium or croscarmellose sodium sodium, and a stabilizer may be mentioned, for 25 example, a hindered phenol series antioxidant, or a benzotriazole series or hindered amine series UV absorber, etc. A pH adjuster may be mentioned, for example, phosphoric acid, acetic acid or sodium hydroxide, and an antifungal and antiseptic may be mentioned, for example, a fungicide for industrial purpose, an antifungal and antiseptic such as 1,2-benzisothiazolin-3-one, etc. A thickening agent may be 30 mentioned, for example, xanthan gum, guar gum, CMC sodium, Gum Arabic, polyvinyl alcohol or montmorillonite, etc. A defoaming agent may be mentioned, for example, a silicone series compound, and an antifreezing agent may be mentioned, for example, propylene glycol or ethylene glycol, etc. However, these auxiliaries are not limited by the above. 35 [0153J An application method of the composition of the present invention may be - 53 mentioned, for example, a foliar spray treatment to individual plants, nursery-box treatment, spray treatment onto the soil surface, soil incorporation after spray treatment onto the soil surface, injection treatment into the soil, soil incorporation after injection treatment into the soil, soil drench, soil incorporation after soil drench, spray treatment 5 to plant seeds, smear treatment to plant seeds, dip treatment to plant seeds or powder dressing treatment to plant seeds, etc., and any application methods generally utilized for a person skilled in the art can give sufficient effects. Also, a method for controlling plant disease in the present invention includes methods in which a plant disease control composition containing Compound (I) of 10 Group a and the fungicidal compound of Group b as effective ingredients is applied, a plant disease control composition containing Compound (I) of Group a as an effective ingredient and a plant disease control composition containing a fungicidal compound of Group b as an effective ingredient are simultaneously applied, and, either one of the plant disease control composition containing Compound (I) of Group a as an effective 15 ingredient or a plant disease control composition containing a fungicidal compound of Group b as an effective ingredient is firstly applied, and then, the other above-mention ed composition is applied. An hour(s) (term) after applying either one of the plant disease control composition containing Compound (I) of Group a as an effective ingredient or the plant disease control composition containing a fungicidal compound of 20 Group b as an effective ingredient is firstly applied till the other above-mentioned composition is applied is, for example, 1 minute to 2 weeks after applying either one of which is applied, preferably 5 minutes to 1 week after applying either one of which is applied, more preferably 10 minutes to 3 days after applying either one of which is applied. 25 Further, the plant disease control composition of the present invention can be prepared as a composition containing the quinoline compound (I) and the fungicidal compound of Group b with high concentrations. The high concentration composition can be used as a spreding liquid by diluting with water. The plant disease control composition of the present invention can be also prepared by mixing a composition 30 containing the quinoline compound (I) with a high concentration, and a composition containing the fungicidal compound of Group b with a high concentration at the time of use to prepare a mixture. This high concentration composition can be used as a spreding liquid by diluting with water (tank mix method). [01541 35 In the plant disease control composition containing the quinoline compound (I) of Group a and the fungicidal compound of Group b as effective ingredients, its applied - 54 amount and a concentration to be applied may vary depending on the crops to be applied, diseases to be controlled, degree of occurrence of diseases, preparation form of the compound, application method and various environmental conditions, etc., and when it is sprayed, it is generally 50 to 10,000 g per hectare, preferably 100 to 5,000 g 5 per hectare as an amount of effective ingredients. When the wettable powder, flowable agent or emulsifiable concentrate is used by diluting with water and spreading, its diluting ratio is generally 5 to 50,000-fold, preferably 10 to 20,000-fold, more preferably 15 to 10,000-fold. In case of the seed disinfection, an amount of the fungicide mixture to be used is generally 0.001 to 50 g, preferably 0.01 to 10 g per kg of 10 the seeds. When the composition of the present invention is applied to individual plants by a foliar spray treatment, spray treatment to the soil surface, injection treatment into the soil, or soil drench, the treatment may be carried out after diluting the chemical to be used by a suitable carrier with a suitable concentration. When the composition of the present invention is contacted to plant seeds, the plant seeds may be dipped into the 15 chemical as such. Also, after diluting the chemical to be used in a suitable carrier with a suitable concentration, the plant seeds may be carried out a dip, powder dressing, spray, or smear treatment. An amount of the preparation to be used for powder dressing, spray or smear treatment is generally 0.05 to 50% or so based on the weight of the dry plant seeds, preferably 0.1 to 30%, but the amount to be used is not limited by 20 these ranges, and may vary depending on the form of the preparation or a kind of plant seeds to be treated. Suitable carriers may include, for example, liquid carriers including water and organic solvents such as ethanol, etc.; inorganic substances such as bentonite, montmorillonite, kaolinite, diatomaceous earth, white clay, talc, clay, vermiculite, gypsum, calcium carbonate, amorphous silica, ammonium sulfate, etc., 25 vegetable organic substances such as soybean powder, wood powder, sawdust, wheat powder, lactose, sucrose, glucose, etc.: or solid carriers such as urea, etc., but the present invention is not limited by these. [01551 The individual plants in present specification are those which live with photo 30 synthesis without any movement, more specifically, there may be mentioned, for example, rice, wheat, barley, corn, grape, apple, pear, peach, yellow peach, persimmon, citrus, soybean, kidney bean, strawberry, potato, cabbage, lettuce, tomato, cucumber, eggplant, water melon, sugar beet, spinach, field pea, pumpkin, sugarcane, tobacco, green pepper, sweet potato, taro, konnyaku, sugar beet, cotton, sunflower, tulip, 35 chrysanthemum or turf, etc., but the present invention is not limited by these. [01561 The plant seeds in the present specification are those which store nutrients for embryo plant to germination and to be agriculturally used for breeding, more specifically, there may be mentioned, for example, seeds of corn, soybean, cotton, rice, sugar beet, wheat, barley, sunflower, tomato, cucumber, eggplant, spinach, field pea, pumpkin, 5 sugarcane, tobacco, green pepper and canola, etc.; seed tuber of taro, potato, sweet potato, konnyaku, etc.; bulb of edible Lily bulbs, tulip, etc., or seed bulb of scallion, etc.; or plants artificially generated by operating the gene, etc. Said plants may be mentioned, for example, transformed seeds such as soybean, corn, cotton, etc., to which herbicidal resistance is provided; rice, tobacco, etc., adapted to cold ground; corn, cotton, potato, etc., 10 to which insecicidal substance-producing ability is provided, etc., which are not inherently present in natural world, but the present invention is not limited by these. [0157] The composition of the present invention can be used by mixing with the other agricultural chemicals, soil conditioners or fertilizing substances such as insecticides, 15 acaricides, nematocides, herbicides and plant growth controllers, etc., as a matter of course, and also possible to use as a mixed preparation with these materials. Insecticides may be mentioned, for example, phosphorus series insecticides such as phenitrothione, diazinon, pyridaphenthi on, chlorpyrifos, malathion, phenthoate, d imethoate, methyl thiometon, prothiofos, DIDVP, acephate, salithion, EPN, etc.; carbamate series insecticides such as 20 NAC, MTMC, BPMC, pirimicarb, carbosuIfan, methomyl, etc.; pyrethroid series insecticides suth as ethofenprox, silafluofen, permethrin, fenvalerate, etc.; neonicotinoid series insecticides such as dinotefuran, ciothianidin, nitenpyram, thiamethoxam, imidacloprid, thiacioprid, acetamiprid, etc.; and fipronil and ethiprole, etc., but the present invention is not limited by these. 25 [0158] The composition and the controlling method of the present invention are effective to, for example, the following mentioned plant diseases, In the following, specific diseases and its fungi or bacteria to be controlled by the present invention may be exemplified: [0159] 30 blast (Pyricularia oryzae), sheath blight (Thanarephorus cucumeri, brown spot (Cochliobolus miyabeanus), "Bakanae" disease (Gibberela fu/ikuroi), seedling blight ( Pythium spp., Fusarium spp., Trichoderma spp Rhizopus spp., Rhizoctonia solanielc.), rice usti aginoi:iea virens (Claviceps virens) and smut (Tilletia barelOyana) of rice; powdery midew (Erysiphe grainisf sp.hordei; f spiritici), rust (Puccinia sfriifornis; 3 5 Puccinia graminis, Puccinia recondita, Puccinia hordes), mottle leaf (Pyrenophora graminea), net blotch (Pyrenop hora teres), fusarium blight (Fusarium graminearurn, Fusarium cIrorum, Fusariurn avenaceum, Microdochium nivale), snow mould ('I phu/a incarnawa, Typhula ishikariensis Micronectriella nivais), loose kernel smut (Ust/iago nuda, 5 Ustilago tr/ici Us/ago nigra, Usil/ago avenae), stinking smut ('Tilelia caries, Tiletla pancici), eye spot (Pseudocercosporella herpotricho/des), foot rot fRhisoclonia cerealis), scald ( Rhynchosporiumsea/is), leaf blight (Septoria tr/ici), giume blotch (Leptosphaeria nodorum) seed ling blight(Fusarium spp., Pyhi spp. Rhizoconia spp., Septoria nodorum, Pyrenophora spp) damping off (Gaeumannomyces graminis), anthracnose 10 (Colletotrichum gramamninicola), ergot (Claviceps purpurea) and spot bl otch (Cochliobolus sativus) of family of wheat; fusarium blight (Fusarium graminearumec.), seedling blight Fusarim avenaceum, Penicilihum spp, Pythium spp., Rhizoc/onia spp), rust (Puccinia sorghi), brown spot (Cochlobolus heterostrophus), smut (Us/ilago maydis), anthracnose (Co//etatrichugramaminicola) and Northern leaf spot (Cochliobo/us carbonum) o f corn; 15 [0160] downy mildew (Plasmopora vicola), rust (Phakopsora ampe/opsidis), powdery mildew (Unc/u/a necator), anthracnose (E/sinoe ampelina), ripe rot (GlomerelI/a cingulata), black rot (Guignardia bidwe/lli), dead arm (Phomopsis virico/a), fry speck (Zygophiala jamaicensis), gray mold (Borryis cinerea), bud blight (Diaporthe medusaea), 20 violet root rot (He//cobasidium mompa) and white root rot (Rosellinia necatrix) of grape vine; powdery mildew (Podosphaera /eucouricha), scab (Venturia aequa/is), alternaria blotch (A/l.ernaria ahternaa (Apple pathozypej, rust (Gymnosporanglum yamadae), blossom blight (Aonil/ia mali), valsa canker (1Vasa ceralosperma), ring rot (Boeryosphaeria berengeriana), anthracnose (Col/eeorichum acuitum), fry speck (Zygophia/ajamaicensis) 25 sooty blotch (Olceodes pomigena), fruit spot (Mycosphaerela pomni), violet root rot (Helicobasidium mompa), white root rot (Rose/lin/a neca/rix), diaporthe canker (Phomopsis ma/i. Diaporthe tanakae) and blotch (Dip/ocarpon mali) of apple; phoma rot (Alternaria a/ternat'a (Japonese pear paiholtype)), scab (Venturia nashicola), rust (Gymnosporangium haraeanum), Physalospora canker (Physa/ospora piricola) and canker (Diaporthe 30 medusaea, Dio porthe eres) of pear; phytophthora rot (Phyophthora cactorum) of European pear; scab (Cladosporium carpophi/um), phomopsis rot (Phomnopsis sp.), phytophthora fruit rot (Phycop hhorn sp.) and anthracnose (Gloeosporium laeticolor) of peach; anthracnose (Glomerela cingulata), young-fruit rot (MonI/n/a kusanoi) and brown rot (Mon/linia fruceicola) of cherry; anthracnose (Gloeosporium kaki), angular leaf spot (Cercospora 35 57 kaki; Mycosphaerella nawae), powdery mildew (Phyllactinia kakikora) of persimmon; melanose (Diaporthe citri), common green mold (Penic/I/umn dig/tatum), blue mold (Penicill/um talicum) and scab (Elsincefawcettii) of citrus; [0161] 5 gray rmold (Botrytis cinerea) of tomato, cucumber, pulse, strawberry, potato, cabbage, eggplant, lettuce, etc.; stem rot (Sclerotinia scieroiorumn) of tomato, cucumber, bean, strawbenry, potato, rape, cabbage, eggplant, lettuce, etc.; seedling blight (Rhizocionia spp., Pythium spp., Fusarium spp., Phythophihora spp, Sc/erotinia sc/erouiorumetc.) of various kinds of vegetables such as tomato, cucumber, bean, Japanese radish, water melon, 0 eggplant, rape, green pepper, spinach, sugar beet, etc.; downy mildew (Pseudoperonospora cubensis), powdery mildew (Sphaerothecafulignea), anthracnose (Colletoirichum lagenarium), gummy stem blight (Didymella bryoniae), fusarium wilt (Fusariun oxysporum) and plytophthora rot (Phytopht hore pares/lice, Phyzophthora melonis, Phytophthora niicctianae, Phytophthora drechs/eri, Phytophthora caps/c/etc.) of oriental 15 melon; early blight (Ahernaria so/ani), leaf mold (Cladosporumfulvam), late blight (Phytophthora infestans), fusarium wilt (Fusariurm oxysporun), root rot (Pythium myriotylurm, Pythiurm dissotocumn) and anthracnose (Co/let orchum phonimoides) of tomato; powdery mile w (Sphaerothecefuiigineaetc), leaf mold (Mycovelosielia naItressii), late blight (Phytophthora infestans) and brown rot (Phyophora caps/cl) of eggplant; alternaria 20 leaf spot (Alter nar/a brass/cae) of rapeseed; alternaria leaf spot (Alternaria brassicaefec.), white spot (Cercosporelia brass/cae), blackleg (Leptospheria maculans), clubroot (Plasmod/ophora brass/ic) and downy mildew (Peronospora brassic) of Brassica vegetables; foot rot (Rhizocronia solan!), yellows (Fuser/um oxysporum) of cabbage; bottom rot (Rhizoczonia so/ani) and yellows (Verde/iliur dahlie) of Chinese cabbage; rust 25 (Puccin/a all/i), altenaria leaf spot (Aternaria porri), southern blight (Sclerotium roIfs//. Sc/cro/iurn refsii) and white tip disease (Phytophihora porr) of wish onion; purple stain (Cercospora kikuchii), sphaceloma scab (Elsinoe glycinnes), black spot (Diapor:he phaseoklumn), rhizoctonia root rot (Rhizoctonia solani), sten rot (Phytophlhora megasperma), downy mildew (Peronospora manshurica), rust (Phakopsora pachyrhizi) and 30 ant hracnose (Co/ieoer/chutru ncaurm) of soybean; anthracnose (Co//etctr/chum lindemnuth/anum) of kidney bean; leaf spot (Mycosphaerclla personatum) and brown leaf spot (Cereospora arachidicela) of peanuts; powdery mildew (Erysiphe pisi) and downy mildew (Peronospora p/si) of pea; downy mildew (Peronospora vic/ae) and phytophthora rot (Phyophthora nicotianae) of broad bean; early blight (Alternaria so/eni), black scurf 35 (Rhizoctonia slan!), late blight (Phytophthere infestans), silver - 58 scurf (Spondylocladium atrovirens), dry spot (Fusarium oxysporum, Fusarium solani) and powdery scab (Spongospora subterranea) of potato; cercospora leaf spot (Cercospora beticola), downy mildew (Peronospora schachtii), aphanomyces root rot (Aphanomyces cochioides) and leaf spot (Phoma batae) of sugar beet; leaf blight 5 (Alternaria dauci) of carrots; powdery mildew (Sphaerotheca humuli), phytophthora rot (Phytophthora nicotianae), anthracnose (Gromerella cingulata) and soft-rotted fruits (Pythium ultimum Trow var. ultimum) of strawberry; [01621 net blister blight (Exobasidium reticulatum), white scab (Elsinoe leucospila), 10 anthracnose (Colletotrichum theae-sinensis) and gray blight (Pestalotiopsis longiseta) of green tea; brown spot (Alternaria alternata (Tobacco pathotype)), powdery mildew (Erysiphe cichoracearum), anthracnose (Colletotrichum tabacum) and black shank (Phytophthora parasitica) of tobacco; damping off (Fusarium oxysporum) of cotton; [01631 15 sclerotinia rot (Sclerotinia sclerotiorum) of sunflower; black spot (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa), phytophthora rot (Phytophthora megasperma) and downy mildew (Peronospora sparsa) of rose; leaf blight (Septoria chrysanthemi-indici), rust (Puccinia horiana) and phytophthora rot (Phytophthora cactorum) of chrysanthemum; or 20 10164] brown patch (Rhizoctonia solani), dollar spot (Sclerotinia homoeocarpa), Curvularia leaf blight (Curvularia geniculata), rust (Puccinia zoysiae), Helmintho sporium leaf blight (Cochliobolus sp.), scald (Rhynchosporium secalis), damping off (Gaeumannomyces graminis), anthracnose (Colletotrichum graminicola), typhula 25 brown snow blight (Typhula incarnata), typhula black snow blight (Typhula ishikariensis), sclerotinia snow blight (Sclerotinia borealis), fairy rings (Marasmius oreadesetc.), pythium blight (Pythium aphanidermatumetc.) and blast (Pyricularia oryzae) of turfgrass, but the present invention is not limited by these. 30 EXAMPLES [01651 In the following, the present invention is more specifically explained by referring to Preparation examples and Test examples. However, the present invention is not limited only by Preparation examples and Test examples. Incidentally, all the 35 numerical value of the formulation amounts of the respective components described in the following Preparation examples mean part(s) by weight.
- 59 101661 Compounds A (a-14), B (a-18) and C (a-20) in compound (I: Group a) to be used in the following Preparation examples and Test examples are compounds of compounds Nos. 1-866, 1-929 and 1-930 in WO 2005/070917, respectively, and 5 described in Examples 114, 177 and 178. Their chemical structures are shown in Table 1. [0167] [Table 1] Compound RI R2 R3 R4 Xn Ym A (a-14) Me Me Me Me 5-F H B (a-18) Me Me F F H H C (a-20) Me Me F F 5-F H 10 101681 Also, compounds 2001 to 2009 of the fungicidal compounds in Group b to be used in the following Preparation examples and Test examples are compounds represented by the formula (II): [Formula 2] 0 R 17 Ri H R16 O N R19 NN H (II 15 0 and R 16 to R19 are each as shown in Table 2. [0169] - 60 [Table 21 Compound No. R' R R 8 R 9 2001 ~Me (b-23-1) iPr iPr H Me 2002 i ~ ~ -zM e (b-23-2) iPr tBu H (b-20-3) iPr iPr H 2004F3CCH2 iPr H NMe (20-5) F3CCH2 tBu H M e (b26)
F
3
CCH
2 iPr H (b27)
F
3
CCH
2 Me H Me (b2-8) iPr H Me (b-2-9) i
P
r
C
F3 H Me (b-23-9) 10170] Preparation example 1 Wettable powder (al-1) 5 Either one of the compounds (10 parts) among Compounds A, B and C as Component I (Group a), either one of the following mentioned compounds (added amount) as Component II (Group b), Neogen Powder (0.5 part), Carplex (0.5 part), GOHSENOL (0.2 part), Radiolite (0.8 part) and H fine powder (used as the remainder so that the total became 100 parts) were crushed and mixed to obtain Wettable powder 10 (al-1). Compound (added amount) as Component II (Group b) was Maneb (88 parts), Oxpoconazole fumarate (5 parts), Captan (66 parts), Boscalid (25 parts), Diethofencarb (6 parts), Procymidone (25 parts), Fludioxonil (10 parts), Thiophanate-methyl (35 - 61 parts), Fenhexamid (25 parts), Fluazinam (10 parts), Iminoctadine trialbesilate (20 parts), Polyoxins complex (10 parts), Iprodione (25 parts), Penthiopyrad (5 parts), Simeconazole (5 parts), Azoxystrobin (4 parts), Kasugamycin monohydrochloride (1 part), Validamycin (5 parts), Tricyclazole (5 parts), Ferimzone (5 parts), Phthalide (5 5 parts), Diclomezine (10 parts), Flutolanil (12 parts), Furametpyr (5 parts), Hexacona zole (1 parts), Fenbuconazole (2.2 parts), Tebuconazole (10 parts), Kresoxim-methyl (10 parts), Triadimefon (5 parts), Mepanipyrim (10 parts), Imibenconazole (7.5 parts), Cyflufenamid (0.8 parts), Fenarimol (2 parts), Triflumizole (3 parts), Fosetyl-aluminium (80 parts), Cymoxanil (10 parts), cupric hydroxide (27.6 parts), TPN (20 parts), 10 Propamocarb hydrochloride (80 parts), Cyazofamid (4.7 parts), Metalaxyl (5 parts), Ethaboxam (5 parts), Mancozeb (3.7 parts), Famoxadone (5 parts), Benthiavalicarb isopropyl (5 parts), Metalaxyl M (5 parts), Dimethomorph (10 parts) or Compound 2001 to 2009 (5 parts). [0171] 15 Preparation example 2 Wettable powder (a2- 1) Either one of the compounds (5 parts) among Compounds A, B and C as Component I (Group a), either one of the compounds mentioned in Preparation example 1 as Component II (Group b), Neogen Powder (0.5 part), Carplex (0.5 part), GOHSENOL (0.2 part), Radiolite (0.8 part) and H fine powder (used as the remainder 20 so that the total became 100 parts) were crushed and mixed to obtain Wettable powder (a2-1). 101721 Preparation example 3 Dust formulation (bl-1) Either one of the compounds (2 parts) among Compounds A, B and C as 25 Component I (Group a), either one of the following mentioned compounds (added amount) as Component II (Group b) and clay (used as the remainder so that the total became 100 parts) were uniformly crushed and mixed to obtain Dust formulation (bI 1). Compounds (added amount) as Component II (Group b) were Captan (40 30 parts), Boscalid (25 parts), Procymidone (25 parts), Thiophanatemethyl (35 parts), Fluazinam (25 parts), Iminoctadine trialbesilate (15 parts), Polyoxins complex (25 parts), Iprodione (25 parts), Simeconazole (10 parts), Flutolanil (5 parts) or Validamycin (0.3 part). [01731 35 Preparation example 4 Dust formulation (b2-1) Either one of the compounds (10 parts) among Compounds A, B and C as - 62 Component I (Group a), either one of the compounds mentioned in Preparation example 3 as Component II (Group b), flocculant (Driless A: 0.3 part), clay (50 parts) and calcium carbonate (used as the remainder so that the total became 100 parts) were mixed, and pulverized by a pin mill to obtain Dust formulation (b2-1). 5 [0174] Preparation example 5 Flowable (c1) Either one of the compounds (5 parts) among Compounds A, B and C as Component I (Group a), either one of the following mentioned compounds (added amount) as Component II, propylene glycol (7 parts), sodium lignosulfate (4 parts), 10 sodium dioctylsulfosuccinate (2 parts) and water (used as the remainder so that the total became 100 parts) were wet pulverized by a sand grinder to obtain Flowable (ci). Compounds (added amount) as Component II (Group b) were Azoxystrobin (10 parts), Tricyclazole (10 parts), Ferimzone (10 parts), Phthalide (10 parts), Flutolanil (3.5 parts), Hexaconazole (10 parts), Fenbuconazole (II parts), Tebuconazole (10 15 parts), Procymidone (20 parts), Cyazofamid (4 parts), TPN (20 parts), Iminoctadine trialbesilate (5 parts) or sulfur (30 parts). 101751 Preparation example 6 Emulsifiable concentrate (d1-1) Either one of the compounds (10 parts) among Compounds A, B and C as 20 Component I (Group a), either one of the following mentioned compounds (added amount) as Component II (Group b), cyclo hexane (10 parts), Tween 20 (surfactant: 20 parts) and xylene (used as the remainder so that the total became 100 parts) were uniformly dissolved and mixed to obtain Emulsifiable concentrate (d l-1). Compounds (added amount) as Component II (Group b) were Boscalid (20 25 parts), Procymidone (20 parts), Flutolanil (3.5 parts), Fenbuconazole (II parts), Tebuconazole (10 parts), Triflumizole (15 parts), TPN (20 parts), Ipconazole (10 parts), Polyoxins complex (5 parts), Tetraconazole (10 parts), Triforine (15 parts), Triadimefon (25 parts) or Difenoconazole (25 parts). [01761 30 Preparation example 7 Granules (e1-1) Either one of the compounds (5 parts) among Compounds A, B and C as Component I (Group a), either one of the following mentioned compounds (added amount) as Component II (Group b), wetting agent (Neopelex No. 6F Powder: 0.5 part), binder (AMICOL No. 1: 3 parts), talc (15 parts) and clay (used as the remainder so that 35 the total became 100 parts) were mixed, hydrolyzed and then, molded by a pellet mill. The obtained molded product was dried and seived to obtain Granules (el-1).
- 63 Compounds (added amount) as Component II (Group b) were Boscalid (25 parts), Procymidone (25 parts), Fludioxonil (10 parts), Fenhexamid (25 parts), Iminoctadine trialbesilate (15 parts), Penthiopyrad (10 parts), Simeconazole (10 parts), Azoxystrobin (10 parts), Validamycin (2.5 parts), Tricyclazole (10 parts), Flutolanil (3.5 5 parts), Furametpyr (10 parts), Tebuconazole (10 parts), Metalaxyl (5 parts), Mancozeb (7 parts), Diclocymet (3 parts), Metominostrobin (10 parts), Carpropamid (15 parts), Probenazole (10 parts) or Isoprothiolane (5 parts). [01771 Comparative preparation example 1 Wettable powder (al -2) 10 Either one of the compounds (10 parts) among Compounds A, B and C as Component I (Group a), Neogen Powder (0.2 part), Carplex (0.2 part), GOHSENOL (0.1 part), Radiolite (1 part) and H fine powder (used as the remainder so that the total became 100 parts) were pulverized and mixed to obtain Wettable powder (a 1-2). [0178] 15 Comparative preparation example 2 Wettable powder (a2-2) Either one of the compounds (5 parts) among Compounds A, B and C as Component I (Group a), Neogen Powder (0.2 part), Carplex (0.2 part), GOHSENOL (0.1 part), Radiolite (1 part) and H fine powder (used as the remainder so that the total became 100 parts) were pulverized and mixed to obtain Wettable powder (a2-2). 20 [0179] Comparative preparation example 3 Dust formulation (b 1-2) Either one of the compounds (2 parts) among Compounds A, B and C as Component I (Group a) and clay (98 parts) were uniformuly pulverized and mixed to obtain Powder (bl-2). 25 [0180] Comparative preparation example 4 Dust formulation (b2-2) Either one of the compounds (10 parts) among Compounds A, B and C as Component I (Group a), flocculant (Driless A: 0.3 part), clay (50 parts), calcium carbonate (used as the remainder so that the total became 100 parts) were mixed and 30 pulverized by a pin mill to obtain Powder (b2-2). [0181] Comparative preparation example 5 Flowable (cI -1) Either one of the compounds (5 parts) among Compounds A, B and C as Component I (Group a), propylene glycol (7 parts), sodium lignosulfate (4 parts), 35 sodium dioctylsulfosuccinate (2 parts) and water (82 parts) were wet pulverized by a sand grinder to obtain Flowable (cl-1).
- 64 [0182] Comparative preparation example 6 Emulsifiable concentrate (dl-2) Either one of the compounds (10 parts) among Compounds A, B and C as Component I (Group a), cyclo hexane (10 parts), xylene (50 parts) and Tween 20 5 (surfactant: used as the remainder so that the total became 100 parts) were uniformly dissolved and mixed to obtain Emulsifiable concentrate (dl-2). [01831 Comparative preparation example 7 Granules (e 1-2) Either one of the compounds (5 parts) among Compounds A, B and C as 10 Component I (Group a), wetting agent (Neopelex No. 6F Powder: 0.5 part), binder (AMICOL No. 1: 3 parts), talc (15 parts) and clay (used as the remainder so that the total became 100 parts) were uniformly mixed, hydrolyzed, and then, molded by a pellet mill. The obtained molded product was dried and seived to obtain Granules (el-2). [0184] 15 Test example 1 Tomato gray mold preventive test (Diethofencarb-resistant strain) In a greenhouse, tomato (variety: Ohgata-Fukuju) planted in a plastic pot having a diameter of 5 cm was grown to the 2nd to 3rd-leaf stage. Wettable powder prepared according to Preparation example 1 and Preparation example 2 were diluted to a predetermined concentration with water, and sprayed with a spray gun with 10 ml per 20 2 pots. After drying the chemical liquid, a conidiospore suspension prepared from Botrytis cinerea (Diethofencarb-resistant strain) which had been previously cultured on a MY medium were inoculated by spraying. After inoculation, the pots were placed in a high-humidity chamber (20 to 22 0 C), and after 2 days, the pots were taken out and controlling effects were examined. In the examination, a ratio of lesion area occupied 25 per whole leaflet of tomato was determined according to the indexes of the following mentioned degree of diseases. Also, from the average degree of diseases of each treated district, the control value was calculated from the following numerical formula. Incidentally, as a comparison, Wettable powder prepared according to Comparative preparation example 1 and Comparative preparation example 2 were similarly tested, 30 and controlling effects were examined. The results of the spreading test and the theoretical value according to the Colby's formula are shown in Table 3. [0185] Index of degree of disease Index Degree of disease 35 0 No lesion 1 Lesion area is less than 1/3 of whole leaflet - 65 2 Lesion area is 1/3 or more and less than 2/3 of whole leaflet 3 Lesion area is 2/3 or more of whole leaflet [0186] Incidentally, average values of the each treated district and non-treated district 5 were used as the degree of diseases. [0187] The control value was calculated from the following formula. Control value = (1-Ratio of diseased leaflets in the treated district /Ratio of diseased leaflets in the non-treated district) x 100 10 [0188] Here, Colby's formula is X = P+Q-PxQ/100, wherein X is a theoretical value of the control value, P is a control value where a certain chemical is spread alone, and Q is a control value where chemicals to be used in combination are spread in admixture. [0189] - 66 [Table 3-1] Effective ingredient in the Treatment Control Theoretical preparation concentration value value prepaation(ppm) A + Maneb 10+ 177.5 90 86 A + Oxpoconazole fumarate 10 + 10 100 83 A + Captan 10+ 133.3 100 89 A + Boscalid 10+50 100 86 A + Diethofencarb 10 + 12.5 90 83 A + Procymidone 10+50 100 86 A + Fludioxonil 10 + 20 100 94 A + Thiophanate-methyl 10 + 70 100 91 A + Fenhexamid 10+50 100 92 A + Fluazinam 10+20 100 83 A + Iminoctadine trialbesilate 10 + 40 100 94 A + Polyoxins complex 10 + 20 100 93 A + Iprodione 10+50 100 94 A + Penthiopyrad 10+ 10 100 89 A + Simeconazole 10 + 10 100 89 B + Maneb 10+177.5 100 86 B + Oxpoconazole fumarate 10 + 10 100 83 B + Captan 10+ 133.3 100 89 B + Boscalid 10 + 50 100 86 B + Diethofencarb 10+ 12.5 100 83 B + Procymidone 10+50 100 86 B + Fludioxonil 10 + 20 100 94 B + Thiophanate-methyl 10 + 70 100 91 B + Fenhexamid 10+50 100 92 B + Fluazinam 10+20 95 83 B + Iminoctadine trialbesilate 10 + 40 100 94 B + Polyoxins complex 10 + 20 100 93 B + Iprodione 10+50 100 94 B + Penthiopyrad 10+ 10 100 89 B + Simeconazole 10+ 10 100 89 [0190] - 67 [Table 3-2] C + Maneb 10+ 177.5 95 83 C + Oxpoconazole fumarate 10 + 10 95 80 C + Captan 10+ 133.3 100 87 C + Boscalid 10+50 100 83 C + Diethofencarb 10 + 12.5 93 80 C + Procymidone 10 +50 93 83 C + Fludioxonil 10 + 20 100 93 C + Thiophanate-methyl 10 + 70 100 89 C + Fenhexamid 10+50 100 90 C + Fluazinam 10 + 20 90 80 C + Iminoctadine trialbesilate 10 + 40 100 93 C + Polyoxins complex 10 + 20 100 92 C + Iprodione 10+50 100 93 C + Penthiopyrad 10 + 10 100 87 C + Simeconazole 10 + 10 98 87 Maneb 177.5 17 Oxpoconazole fumarate 10 0 Captan 133.3 33 Boscalid 50 17 Diethofencarb 12.5 0 Procymidone 50 17 Fludioxonil 20 67 Thiophanate-methyl 70 43 Fenhexamid 50 50 Fluazinam 20 0 Iminoctadine trialbesilate 40 67 Polyoxins complex 20 60 Iprodione 50 67 Penthiopyrad 10 33 Simeconazole 10 33 A 10 83 B 10 83 C 10 80 [01911 From the results shown in the above-mentioned Table 3, it could be understood 5 that synergistic effects could be obtained when Compound A, B or C and the compound of Group b are used in combination. Incidentally, even when Compound A, B or C and the compound of Group b are used in combination, no chemical damage symptom was admitted in the plant material, tomato (variety: Ohgata-Fukuju). [0192] 10 Test example 2 Rice blast preventive test In a greenhouse, rice (variety: Sachikaze) planted in a plastic pot having a - 68 diameter of 5 cm was grown to the 3rd to 4th-leaf stage. Spray was carried out in the same manner as in Test example 1, and after 3 days from the spray, a conidiospore suspension prepared from Pyricularia oryzae which had been previously cultured on an oatmeal medium were inoculated by spraying. After inoculation, the pots were placed 5 in a high-humidity chamber (20 to 23*C), and taken out on the next day and transferred into a greenhouse. Controlling effects were examined after 7 days from the inoculation. In the examination, a ratio of lesion area occupied per one leaf of rice was determined according to the same index as in Test example 1, and the control value and the theoretical value according to Colby's formula were similarly calculated. The 10 results are shown in Table 4. [01931 - 69 [Table 4-1] Effective ingredient in the Treatment Control Theoretical preparation concentration value value (ppm) A + Azoxystrobin 10 + 8 67 38 A + Kasugamycin 10+2 50 38 monohydrochloride A + Validamycin 10+10 50 44 A + Tricyclazole 10+10 50 36 A + Ferimzone 10+ 10 60 38 A + Phthalide 10+ 10 60 51 A + Diclomezine 10 + 20 50 44 A + Flutolanil 10+25 50 38 A + Furametpyr 10+ 10 60 36 A + Compound 2001 10+5 67 55 A + Compound 2002 10+5 78 55 A + Compound 2003 10+5 78 66 A + Compound 2004 10+5 97 78 A + Compound 2005 10+5 98 78 A + Compound 2006 10+5 97 78 A + Compound 2007 10+5 100 78 A + Compound 2008 10+5 78 55 A + Compound 2009 10+5 100 78 B + Azoxystrobin 10 + 8 90 84 B + Kasugamycin 10+2 90 84 monohydrochloride B + Validamycin 10+10 98 86 B + Tricyclazole 10+ 10 98 84 B + Ferimzone 10+ 10 97 84 B + Phthalide 10 + 10 97 88 B + Diclomezine 10 + 20 98 86 B + Flutolanil 10 + 25 98 84 B + Furametpyr 10+ 10 97 84 B + Compound 2001 10+5 96 89 B + Compound 2002 10 + 5 96 89 B+Compound2003 10+5 98 91 B + Compound 2004 10+5 100 94 B + Compound 2005 10+5 100 94 B + Compound 2006 10+5 100 94 B + Compound 2007 10+5 100 94 B + Compound 2008 10+5 100 89 B + Compound 2009 10+5 100 94 [0194] - 70 [Table 4-2] C + Azoxystrobin 10 + 8 95 79 C + Kasugamycin 10 + 2 89 79 monohydrochloride C + Validamycin 10 + 10 98 82 C + Tricyclazole 10 + 10 95 79 C + Ferimzone 10+10 97 79 C + Phthalide 10+ 10 97 84 C + Diclomezine 10 + 20 100 82 C + Flutolanil 10 + 25 95 79 C + Furametpyr 10+ 10 97 79 C + Compound 2001 10+5 95 85 C + Compound 2002 10+5 96 85 C + Compound 2003 10+5 98 89 C + Compound 2004 10+5 100 93 C + Compound 2005 10+5 100 93 C + Compound 2006 10+5 100 93 C + Compound 2007 10+5 100 93 C + Compound 2008 10+5 100 85 C + Compound 2009 10+5 100 93 Azoxystrobin 8 6.7 Kasugamycin 2 6.7 monohydrochloride Validamycin 10 17 Tricyclazole 10 3.3 Ferimzone 10 6.7 Phthalide 10 27 Diclomezine 20 17 Flutolanil 25 6.7 Furametpyr 10 3.3 Compound 2001 5 33 Compound 2002 5 33 Compound 2003 5 50 Compound 2004 5 67 Compound 2005 5 67 Compound 2006 5 67 Compound 2007 5 67 Compound 2008 5 33 Compound 2009 5 67 A 10 33 B 10 83 C 10 78 [0195] From the results shown in the above-mentioned Table 4, it could be understood 5 that synergistic effects could be obtained when Compound A, B or C and the compound - 71 of Group b are used in combination. Incidentally, even when Compound A, B or C and the compound of Group b are used in combination, no chemical damage symptom was admitted in the plant material, rice (variety: Sachikaze). 101961 5 Test example 3 Rice blast curative test In a greenhouse, rice (variety: Sachikaze) planted in a plastic pot having a diameter of 5 cm was grown to the 3rd to 4th-leaf stage. A conidiospore suspension prepared from Pyricularia oryzae which had been previously cultured on an oatmeal medium were inoculated by spraying. After inoculation, the pots were placed in a 10 high-humidity chamber (20 to 23'C) and taken out on the next day, and spray was carried out in the same manner as in Test example 1. After drying the chemical liquid, the pots were transferred into a greenhouse, and controlling effects were examined after 7 days from the spray. In the examination, a ratio of lesion area occupied per one leaf of rice was determined according to the same index as in Test example 1, and the 15 control value and the theoretical value according to Colby's formula were similarly calculated. The results are shown in Table 5. [0197] - 72 [Table 51 Effective ingredient in the Treatment Control Theoretical preparation concentration value value prepaation(ppm) A + Azoxystrobin 10 + 8 96 79 A + Kasugamycin 10+2 96 77 monohydrochloride A + Validamycin 10+10 89 77 A + Tricyclazole 10+10 89 77 A + Ferimzone 10+ 10 89 77 A + Phthalide 10+ 10 89 77 A + Diclomezine 10 + 20 89 77 A + Flutolanil 10 + 25 89 77 A + Furametpyr 10+10 89 77 B + Azoxystrobin 10 + 8 96 86 B + Kasugamycin 10+2 96 85 monohydrochloride B + Validamycin 10+ 10 94 85 B + Tricyclazole 10+ 10 94 85 B + Ferimzone 10+10 94 85 B + Phthalide 10+10 96 85 B + Diclomezine 10 + 20 96 85 B + Flutolanil 10 + 25 94 85 B + Furametpyr 10+ 10 100 87 C + Azoxystrobin 10 + 8 94 86 C + Kasugamycin 10+2 96 85 monohydrochloride C + Validamycin 10 + 10 96 85 C + Tricyclazole 10+ 10 96 85 C + Ferimzone 10+ 10 96 85 C + Phthalide 10+10 96 85 C + Diclomezine 10 + 20 91 85 C + Flutolanil 10+25 91 85 C + Furametpyr 10+ 10 94 87 Azoxystrobin 8 1.8 Kasugamycin 2 0 monohydrochloride Validamycin 10 0 Tricyclazole 10 0 Ferimzone 10 0 Phthalide 10 0 Diclomezine 20 0 Flutolanil 25 0 Furametpyr 10 11 A 10 79 B 10 86 C 10 86 - 73 [01981 From the results shown in the above-mentioned Table 5, it could be understood that synergistic effects could be obtained when Compound A, B or C and the compound of Group b are used in combination. Incidentally, even when Compound A, B or C 5 and the compound of Group b are used in combination, no chemical damage symptom was admitted in the plant material, rice (variety: Sachikaze). [0199] Test example 4 Cucumber powdery mildew preventive test In a greenhouse, cucumber (variety: Sagamihanpalcu) planted in a plastic pot 10 having a diameter of 5 cm was grown to the 3rd to 5th-leaf stage. Spray was carried out in the same manner as in Test example 1, and 3 days after the spray, a conidiospore suspension prepared from Sphaerothecafuliginea were inoculated on the leaf surface. After inoculation, the pots were placed in a thermostatic greenhouse (20 to 25*C), and controlling effects were examined after 7 days from the inoculation. In the 15 examination, a ratio of lesion area occupied per one leaf of cucumber was determined according to the same index as in Test example 1, and the control value and the theoretical value according to Colby's formula were similarly calculated. The results are shown in Table 6. 102001 - 74 [Table 6-1] Effective ingredient in the Treatment Control Theoretical concentration vauvle preparation (ppm) value value A + Hexaconazole 10+2 67 58 A + Fenbuconazole 10 +4.4 75 63 A + Tebuconazole 10+20 75 67 A + Simeconazole 10 + 10 67 50 A + Kresoxim-methyl 10 + 20 67 58 A + Triadimefon 10+ 10 67 50 A + Mepanipyrim 10+20 60 50 A + Imibenconazole 10 + 15 73 67 A + Cyflufenamid 10 + 1.7 83 67 A + Fenarimol 10+4 93 83 A + Triflumizole 10 + 6 83 67 B + Hexaconazole 10 + 2 93 67 B + Fenbuconazole 10+4.4 83 71 B + Tebuconazole 10 + 20 100 73 B + Simeconazole 10 + 10 83 60 B + Kresoxim-methyl 10 + 20 92 67 B + Triadimefon 10 + 10 73 60 B + Mepanipyrim 10 + 20 67 60 B + Imibenconazole 10 + 15 83 73 B + Cyflufenamid 10+1.7 93 73 B + Fenarimol 10+4 92 87 B + Triflumizole 10+6 93 73 [02011 75 [Table 6-2] C + Hexaconazole 10+2 85 71 C + Fenbuconazole 10 + 4.4 88 74 C + Tebuconazole 10 + 20 100 77 C + Simeconazole 10 10 88 65 C + Kresoxim-methyl 10 + 20 90 71 C + Triadirefon 10-+ 10 76 65 C+Mepanipyrim 10+20 72 65 C +- imibenconazole 10 + 15 90 77 C Cyflufenamid 10 + 1.7 100 77 C+Fenariol 10 + 4 98 88 C + Triflumizole+ 6 98 . 77 HNexaconazole217 Fenbuconazole 4.4 27 Tebuconazole 20 33 Simeconazole 10 0 Kresoxim-imethyl 20 17 Triadimefon 10 0 Mepanipyrim 20 0 imibenconazole 15 33 Cyflufenaniid 1.7 33 Fenarimol 4 67 Triflumizole 6 33 A 10 50 B 10 60 C 10 65 [0202] From the results shown in the above-mentioned Table 6, it could be understood that 5 synergistic effects could be obtained when Compound A, B or C and the compound o Group b are used in combination. Incidentally, even when Compound A, B or C and the compound of Group b are used in combination, no chemical damage symptom was admitted in the plant material, cucumber (variety: Sagamihanpaku). [0203] 10 Test example 5 Cucumber powdery mildew curative test In a greenhouse, cucumber (variety: Sagamihanpaku) planted in a plastic pot having a diameter of 5 cm was grown to the 3rd to 5th-leaf stage. A conidiospore suspension prepared from Sphaerohecafuliginea were inoculated on the leaf surface, and the pots were transferred into a thermostatic greenhouse (20 to 25"C). Two days after inoculation, spray 15 was carried out in the same manner as in Test example 1. After drying the chemical liquid, the pots were transferred into a thermostatic greenhouse, and controlling effects were examined after 7 days from the inoculation, In the - 76 examination, a ratio of lesion area occupied per one leaf of cucumber was determined according to the same index as in Test example 1, and the control value and the theoretical value according to Colby's formula were similarly calculated. The results are shown in Table 7. 5 [02041 [Table 7-1] Effective ingredient in the Treatment Control Theoretical preparation concentration value value prepaation(ppm) A + Hexaconazole 10+2 100 92 A + Fenbuconazole 10 +4.4 100 92 A + Tebuconazole 10 +20 100 89 A + Simeconazole 10 + 10 89 78 A + Kresoxim-methyl 10 + 20 96 89 A + Triadimefon 10 + 10 96 89 A + Mepanipyrim 10+20 100 92 A + Imibenconazole 10 + 15 100 92 A + Cyflufenamid 10 + 1.7 100 89 A + Fenarimol 10+4 100 93 A + Triflumizole 10+6 100 89 B + Hexaconazole 10+2 100 93 B + Fenbuconazole 10 + 4.4 100 93 B + Tebuconazole 10 + 20 100 91 B + Simeconazole 10 + 10 100 82 B + Kresoxim-methyl 10 + 20 98 91 B + Triadimefon 10+10 100 91 B + Mepanipyrim 10+20 100 93 B + Imibenconazole 10 + 15 100 93 B + Cyflufenamid 10+ 1.7 100 91 B + Fenarimol 10+4 100 94 B + Triflumizole 10+6 100 91 [0205] - 77 [Table 7-2] C + Hexaconazole 10 + 2 100 93 C + Fenbuconazole 10 + 4.4 100 93 C + Tebuconazole 10+20 100 91 C + Simeconazole 10+10 100 82 C + Kresoxim-methyl 10 + 20 97 91 C + Triadimefon 10+ 10 100 91 C + Mepanipyrim 10+20 100 93 C + Inibenconazole 10 + 15 100 93 C + Cyflufenamid 10+1.7 100 91 C + Fenarimol 10+4 100 94 C + Triflumizole 10 + 6 97 91 Hexaconazole 2 75 Fenbuconazole 4.4 75 Tebuconazole 20 67 Simeconazole 10 33 Kresoxim-methyl 20 67 Triadimefon 10 67 Mepanipyrim 20 75 Imibenconazole 15 75 Cyflufenamid 1.7 67 Fenarimol 4 78 Triflumizole 6 67 A 10 67 B 10 73 C 10 73 [0206] From the results shown in the above-mentioned Table 7, it could be understood 5 that synergistic effects could be obtained when Compound A, B or C and the compound of Group b are used in combination. Incidentally, even when Compound A, B or C and the compound of Group b are used in combination, no chemical damage symptom was admitted in the plant material, cucumber (variety: Sagamihanpaku). [02071 10 Test example 6 Tomato late blight preventive test In a greenhouse, tomato (variety: Ohgata-Fukuju) planted in a plastic pot having a diameter of 5 cm was grown to the 2nd to 3rd-leaf stage. Spray was carried out in the same manner as in Test example 1, and after drying the chemical liquid, the pots were transferred into a greenhouse. After 3 days from the spray, a sporangium 15 suspension of Phytophthora infestans were inoculated by spraying. After inoculation, the pots were placed in a high-humidity chamber (20 to 22'C), transferred into a greenhouse on the next day, and controlling effects were examined after 7 days from the - 78 inoculation. A ratio of lesion area occupied per one leaf of tomato was determined according to the same index as in Test example 1, and the control value and the theoretical value according to Colby's formula were similarly calculated. The results are shown in Table 8. 5 102081 [Table 8-1] Effective ingredient in the Treatment Control Theoretical preparation concentration value value preparatio ppm) A + Fosetyl-aluminium 10 + 160 17 8.3 A + Cymoxanil 10+20 75 50 A + cupric hydroxide 10+55.3 33 17 A + TPN 10+40 17 0 A + Propamocarb hydrochloride 10 + 160 17 0 A + Cyazofamid 10+ 9.4 100 92 A + Metalaxyl 10+10 67 58 A + Ethaboxam 10+10 93 83 A + Mancozeb 10+7.5 83 67 A + Famoxadone 10+ 10 33 17 A + Azoxystrobin 10 + 8 83 67 A + Benthiavalicarb-isopropyl 10 + 10 93 80 A + Metalaxyl M 10+10 42 33 A + Dimethomorph 10 + 20 75 50 B + Fosetyl-aluminium 10 + 160 33 8.3 B + Cymoxanil 10+20 100 50 B + cupric hydroxide 10+55.3 33 17 B+TPN 10+40 40 0 B + Propamocarb hydrochloride 10 + 160 33 0 B + Cyazofamid 10+9.4 100 92 B + Metalaxyl 10+10 83 58 B + Ethaboxam 10+ 10 97 83 B + Mancozeb 10+7.5 83 67 B + Famoxadone 10+ 10 33 17 B + Azoxystrobin 10+8 83 67 B + Benthiavalicarb-isopropyl 10 + 10 100 80 B + Metalaxyl M 10+10 67 33 B + Dimethomorph 10+ 20 83 50 [02091 - 79 [Table 8-21 C + Fosetyl-aluminium 10 + 160 17 8.3 C + Cymoxanil 10+20 92 50 C + cupric hydroxide 10+55.3 33 17 C + TPN 10+40 33 0 C + Propamocarb hydrochloride 10 + 160 17 0 C + Cyazofamid 10 + 9.4 100 92 C + Metalaxyl 10+ 10 75 58 C + Ethaboxam 10+10 92 83 C + Mancozeb 10+7.5 83 67 C + Famoxadone 10+10 33 17 C + Azoxystrobin 10 + 8 83 67 C + Benthiavalicarb-isopropyl 10 + 10 92 80 C + Metalaxyl M 10+10 67 33 C + Dimethomorph 10 + 20 70 50 Fosetyl-aluminium 160 8.3 Cymoxanil 20 50 cupric hydroxide 55.3 17 TPN 40 0 Propamocarb hydrochloride 160 0 Cyazofamid 9.4 92 Metalaxyl 10 58 Ethaboxam 10 83 Mancozeb 7.5 67 Famoxadone 10 17 Azoxystrobin 8 67 Benthiavalicarb-isopropyl 10 80 Metalaxyl M 10 33 Dimethomorph 20 50 A 10 0 B 10 0 C 10 0 [0210] From the results shown in the above-mentioned Table 8, it could be understood 5 that synergistic effects could be obtained when Compound A, B or C and the compound of Group b are used in combination. Incidentally, even when Compound A, B or C and the compound of Group b are used in combination, no chemical damage symptom was admitted in the plant material, tomato (variety: Ohgata-Fukuju). [0211] 10 Test example 7 Tomato late blight curative test In a greenhouse, tomato (variety: Ohgata-Fukuju) planted in a plastic pot having a diameter of 5 cm was grown to the 2nd to 3rd-leaf stage. A sporangium suspension of Phytophthora infestans were inoculated, the pots were placed in a high- - 80 humidity chamber (20 to 22*C), and taken out on the next day and spray was carried out in the same manner as in Test example 1. After drying the chemical liquid, the pots were transferred into a greenhouse, and controlling effects were examined after 7 days from the inoculation. A ratio of lesion area occupied per one leaf of tomato was 5 determined according to the same index as in Test example 1, and the control value and the theoretical value according to Colby's formula were similarly calculated. The results are shown in Table 9. [0212] [Table 9-11 Effective ingredient in the Treatment Control Theoretical preparation concentration value value A + Fosetyl-aluminium 10 + 160 33 25 A + Cymoxanil 10+20 83 67 A + cupric hydroxide 10+55.3 17 0 A + TPN 10+40 6.7 0 A + Propamocarb hydrochloride 10 + 160 33 0 A + Cyazofamid 10+9.4 33 0 A + Metalaxyl 10+10 76 67 A + Ethaboxam 10+10 76 67 A + Mancozeb 10+7.5 6.7 0 A + Famoxadone 10+10 17 0 A + Azoxystrobin 10 + 8 6.7 0 A + Benthiavalicarb-isopropyl 10 + 10 70 67 A + Metalaxyl M 10 + 10 20 17 A + Dimethomorph 10+20 13 0 B + Fosetyl-aluminium 10 + 160 37 25 B + Cymoxanil 10+20 92 67 B + cupric hydroxide 10+55.3 33 0 B + TPN 10+40 33 0 B + Propamocarb hydrochloride 10 + 160 33 0 B + Cyazofamid 10+9.4 33 0 B+ Metalaxyl 10+ 10 83 67 B + Ethaboxam 10+ 10 83 67 B + Mancozeb 10+7.5 17 0 B + Famoxadone 10+ 10 17 0 B + Azoxystrobin 10+8 17 0 B + Benthiavalicarb-isopropyl 10 + 10 83 67 B + Metalaxyl M 10+10 33 17 B + Dimethomorph 10 + 20 33 0 10 [0213] - 81 [Table 9-2] C + Fosetyl-aluminium 10 + 160 33 25 C + Cymoxanil 10 + 20 73 67 C + cupric hydroxide 10 +55.3 33 0 C+TPN 10+40 33 0 C + Propamocarb hydrochloride 10 + 160 33 0 C + Cyazofamid 10 + 9.4 33 0 C + Metalaxyl 10 + 10 76 67 C + Ethaboxam 10+ 10 83 67 C + Mancozeb 10+7.5 17 0 C + Famoxadone 10+10 17 0 C + Azoxystrobin 10+8 17 0 C + Benthiavalicarb-isopropyl 10 + 10 92 67 C + Metalaxyl M 10+10 67 17 C + Dimethomorph 10 + 20 33 0 Fosetyl-aluminium 160 25 Cymoxanil 20 67 cupric hydroxide 55.3 0 TPN 40 0 Propamocarb hydrochloride 160 0 Cyazofamid 9.4 0 Metalaxyl 10 67 Ethaboxam 10 67 Mancozeb 7.5 0 Famoxadone 10 0 Azoxystrobin 8 0 Benthiavalicarb-isopropyl 10 67 Metalaxyl M 10 17 Dimethomorph 20 0 A 10 0 B 10 0 C 10 0 [0214] From the results shown in the above-mentioned Table 9, it could be understood 5 that synergistic effects could be obtained when Compound A, B or C and the compound of Group b are used in combination. Incidentally, even when Compound A, B or C and the compound of Group b are used in combination, no chemical damage symptom was admitted in the plant material, tomato (variety: Ohgata-Fukuju). [02151 10 Test example 8 Cucumber downy mildew preventive test In a greenhouse, cucumber (variety: Sagamihanpaku) planted in a plastic pot having a diameter of 5 cm was grown to the 3rd to 5th-leaf stage. Spray was carried out in the same manner as in Test example 1, and after drying the chemical liquid, the - 82 pots were transferred into a greenhouse. After 3 days from the spray, a sporangium suspension of Pseudoperonospora cubensis were inoculated. After inoculation, the pots were placed in a high-humidity chamber (20 to 2.5 0 C), transferred into a greenhouse on the next day, and controlling effects were examined after 7 days from the inoculation. A ratio of 5 lesion area occupied per one leaf of cucumber was determined according to the same index as in Test example 1, and the control value and the theoretical value according to Colby's formula were similarly calculated. The results are shown in Table 10. [02161 ITable 10-1] Trecatment Effective ingredient in the cnTratin Control Theoretical preparation (pnm value value A + Fosetyl-aluminium 10 + 160 80 68 A + Cymox anil 10 + 20 80 68 A + cuprichydroxide 10 + 55.3 60 52 A +TPN 10 + 40 100 68 A + Propamocarb hydrochloride 10 + 160 80 36 A + Cyazofamid 10 + 9.4 80 52 A + MetalaKyl 10 + 10 100 68 A + Ethaboxam 10 + 10 80 36 A +Mancozeb 10+7.5 100 68 A +Famoxadone 10+ 10 60 4 A + Azoxytrobin 10 + 8 80 68 A + Benthiavalicarb-isopropyl 10 + 10 100 52 A + MetaIaxyl M 10+ 10 100 68 A + Dimethomorph 10 + 20 100 68 B + Fosetyl-aluminium 10 + 160 92 71 B+ Cymoxanil 10 +20 100 71 B +cupric hydroxide 10+ 55,3 100 57 B + TPN 10 +40 100 71 B + Propamocarb hydrochloride 10 + 160 60 42 B + Cyazof amid 10+ 9.4 100 57 B + Metala ry, 10 + 10 100 71 B+Ethaboxam 10+ 10 100 42 B + Mancozeb 10 + 7.5 100 71 B +Famoxadone 10+ 10 100 14 B + Azoxyttrobin 10 + 8 100 71 B + Benthiavalicarb-isopropyl 10 + 10 100 57 B N- Metalaxyl M 10 + 10 100 71 B + Dtimnehomorph 10 + 20 80 7 10 j02171 - 83 [Table 10-21 C + Fosetyl-aluminium 10 + 160 95 73 C + Cymoxanil 10+20 95 73 C + cupric hydroxide 10+55.3 100 60 C + TPN 10+40 100 73 C + Propamocarb hydrochloride 10 + 160 71 46 C + Cyazofamid 10+ 9.4 100 60 C + Metalaxyl 10 + 10 100 73 C + Ethaboxam 10+10 100 46 C + Mancozeb 10+7.5 100 73 C + Famoxadone 10+ 10 100 33 C + Azoxystrobin 10 + 8 100 73 C + Benthiavalicarb-isopropyl 10 + 10 100 60 C + Metalaxyl M 10+ 10 100 73 C + Dimethomorph 10 + 20 80 73 Fosetyl-aluminium 160 60 Cymoxanil 20 60 cupric hydroxide 55.3 40 TPN 40 60 Propamocarb hydrochloride 160 20 Cyazofamid 9.4 40 Metalaxyl 10 60 Ethaboxam 10 20 Mancozeb 7.5 60 Famoxadone 10 0 Azoxystrobin 8 60 Benthiavalicarb-isopropyl 10 40 Metalaxyl M 10 60 Dimethomorph 20 60 A 10 20 B 10 28 C 10 33 [02181 From the results of the above-mentioned Table 10, it could be understood that 5 synergistic effects could be obtained when Compound A, B or C and the compound of Group b are used in combination. Incidentally, even when Compound A, B or C and the compound of Group b are used in combination, no chemical damage symptom was admitted in the plant material, cucumber (variety: Sagamihanpaku). [02191 10 Test example 9 Cucumber downy mildew curative test In a greenhouse, cucumber (variety: Sagamihanpaku) planted in a plastic pot having a diameter of 5 cm was grown to the 3rd to 5th-leaf stage. A sporangium suspension of Pseudoperonospora cubensis were inoculated, the pots were placed in a high- - 84 humidity chamber (20 to 22*C) and taken out on the next day, and spray was carried out in the same manner as in Test example 1. After drying the chemical liquid, the pots were transferred into a greenhouse, and controlling effects were examined after 7 days from the inoculation. A ratio of lesion area occupied per one leaf of cucumber was 5 determined according to the same index as in Test example 1, and the control value and the theoretical value according to Colby's formula were similarly calculated. Thr results are shown in Table 11. 10220] [Table 11-11 Effective ingredient in the Treatment Control Theoretical preparation concentration value value A + Fosetyl-aluminium 10 + 160 92 72 A + Cymoxanil 10+20 73 72 A + cupric hydroxide 10+55.3 92 58 A+TPN 10+40 93 86 A + Propamocarb hydrochloride 10 + 160 92 17 A + Cyazofamid 10 + 9.4 78 72 A + Metalaxyl 10+10 100 93 A + Ethaboxam 10+ 10 83 72 A + Mancozeb 10 + 7.5 87 72 A + Famoxadone 10+10 100 93 A + Azoxystrobin 10+8 100 93 A + Benthiavalicarb-isopropyl 10 + 10 92 72 A + Metalaxyl M 10+10 100 86 A + Dimethomorph 10 + 20 75 58 B + Fosetyl-aluminium 10 + 160 92 78 B + Cymoxanil 10+20 92 78 B + cupric hydroxide 10 +55.3 97 67 B+TPN 10+40 97 89 B + Propamocarb hydrochloride 10+160 100 33 B + Cyazofamid 10 +9.4 93 78 B + Metalaxyl 10+10 100 94 B + Ethaboxam 10+10 93 78 B + Mancozeb 10+7.5 87 78 B + Famoxadone 10+ 10 100 94 B + Azoxystrobin 10 + 8 100 94 B + Benthiavalicarb-isopropyl 10 + 10 100 78 B + Metalaxyl M 10+10 100 89 B + Dimethomorph 10 + 20 100 67 10 [02211 - 85 [Table 11-2] C + Fosetyl-aluminium 10 + 160 93 78 C + Cymoxanil 10+20 92 78 C + cupric hydroxide 10+55.3 97 67 C + TPN 10+40 97 89 C + Propamocarb hydrochloride 10 + 160 100 33 C + Cyazofamid 10+9.4 93 78 C + Metalaxyl 10+10 100 94 C + Ethaboxam 10+10 93 78 C + Mancozeb 10+7.5 87 78 C + Famoxadone 10+10 100 94 C + Azoxystrobin 10 + 8 100 94 C + Benthiavalicarb-isopropyl 10 + 10 100 78 C + Metalaxyl M 10+10 100 89 C + Dimethomorph 10 + 20 100 67 Fosetyl-aluminium 160 67 Cymoxanil 20 67 cupric hydroxide 55.3 50 TPN 40 83 Propamocarb hydrochloride 160 0 Cyazofamid 9.4 67 Metalaxyl 10 92 Ethaboxam 10 67 Mancozeb 7.5 67 Famoxadone 10 92 Azoxystrobin 8 92 Benthiavalicarb-isopropyl 10 67 Metalaxyl M 10 83 Dimethomorph 20 50 A 10 17 B 10 33 C 10 33 [0222] From the results shown in the above-mentioned Table 11, it could be 5 understood that synergistic effects could be obtained when Compound A, B or C and the compound of Group b are used in combination. Incidentally, even when Compound A, B or C and the compound of Group b are used in combination, no symptom of chemical damage was admitted in the plant material, cucumber (variety: Sagamihanpaku). 10 UTILIZABILITY IN INDUSTRY [0223] The plant disease control composition of the present invention showed a broad - 86 spectrum against various plant pathogens (for example, rice blast (Pyricularia oryzae), and gray mold (Botrytis cinerea) of tomato, cucumber and kidney bean, etc.) including fungi and bacteria resistant to chemicals, and shows excellent controlling effects (synergistic controlling effects) which could never be expected from a single component 5 alone. Also, it shows high plant disease controlling effects against existing fungi and bacteria resistant to chemicals, and no chemical damage against plants can be admitted so that it can be used as an excellent plant disease controlling agent.
Claims (3)
1. A plant disease control composition comprising (Group a) 5 (a) at least one kind of a quinoline compound selected from the group consisting of (a-14) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline, (a-18) 3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline, and (a-20) 3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline, or a salt thereof, and 10 (Group b) (b) one or more fungicides selected from the group consisting of the following Groups: Group (3) an imidazole series compound selected from (b-3-7) Triazoxide 15 Group (4) a carboxamide series compound selected from (b-4-7) Tecloftalam (b-4-8) Mandipropamid (b-4-13) Silthiofam 20 (b-4-15) Flumetover (b-4-17) Zoxamide (b-4-18) Tiadinil (b-4-19) Isotianil (b-4-20) Diclocymet 25 (b-4-21) Fenoxanil (b-4-22) Fluopicolide (b-4-24) Carpropamid (b-4-25) Tolfenpyrad (b-4-26) N-[2-(1,3-dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazol-4-carboxamide 30 (b-4-27) N-12-[1,1'-bi(cyclopropyl)-2-yl]phenyl}-3-(difluoromethyl)-1-methyl-1H-pyrazol-4 carboxamide (b-4-28) 3-(difluoromethyl)-N-(9-isopropyl-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl) 1-methyl-1 H-pyrazol-4-carboxamide (b-4-29) 3-(difluoromethyl)-N-[4'-(3,3-dimethylbutyn-1-yl)biphenyl-2-yl]-1-methyl-1H- - 88 pyrazol-4-carboxamide (b-4-30) 3-(difluoromethyl)-N-[4'-(3-methoxy-3-methylbutyn-1-yl)biphenyl-2-yl]-1-methyl 1H-pyrazol-4-carboxamide and (b-4-31) 3-(difluoromethyl)-1-methyl-N-[1,2,3,4-tetrahydro-9-(1-methylethyl)-1,4 5 methanonaphthalen-5-yl]-1H-pyrazol-4-carboxamide Group (5) an acylalanine series compound selected from (b-5-5) Furalaxyl-M Group (7) 10 a sulfoneamide series compound selected from (b-7-3) Flusulfamide Group (8) a sulfenamide series compound selected from (b-8-1) Tolylfluanid and 15 (b-8-2) Dichlofluanid Group (9) a carbamate series compound selected from (b-9-4) Pyribencarb Group (10) 20 a dithiocarbamate series compound selected from (b-10-8) Polycarbamate Group (12) a guanidine series compound selected from (b-12-4) Dodine 25 Group (13) a pyrimidine series compound selected from (b- 13-7) Dimethirimol (b-13-8) Bupirimate and (b-13-9) Diflumetorim 30 Group (14) a morpholine series compound selected from (b-14-2) Fenpropimorph (b- 14-3) Tridemorph (b- 14-4) Dodemorph and - 89 Group (16) a pyrrole series compound selected from (b-16-2) Fluoroimide and Group (17) 5 an organophosphorous series compound selected from (b-17-2) Edifenphos (b-17-3) Tolclofos-methyl (b-17-4) Iprobenfos and (b-17-5) Pyrazophos 10 Group (19) an antibiotic selected from (b-19-4) Blastcidin-S benzylamino benzenesulfonate (b-19-5) Streptomycin (b- 19-6) Natamycin 15 (b- 19-7) Mildiomycin and (b-19-8) Oxytetracycline Group (20) an organic chlorine series compound selected from (b-20-3) Quintozene 20 Group (21) a triazolopyrimidine series compound selected from (b-21-1) 5-Chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5 a]pyrimidine (b-21-2) 5-Chloro-N-[(1S)-2,2,2-trifluoro-1-methylethyl]-6-(2,4,6-trifluorophenyl) 25 [1,2,4]triazolo[1,5-a]pyrimidine (b-21-3) 5-Chloro-N-[(1R)-1,2-dimethylpropyl]-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5 a]pyrimidine (b-21-4) 5-(Methoxymethyl)-6-octyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine and (b-21-5) 5-Ethyl-6-octyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine 30 Group (22) a benzoyl compound selected from (b-22-1) Metrafenone and (b-22-2) 3-(2,3,4-Trimethoxy-6-methylbenzoyl)-5-chloro-2-methoxy-4-methylpyridine Group (24) - 90 an isoxazolidin series compound selected from (b-24-1) 3-[5-(4-Chloro phenyl)-2,3-dimethylisoxazolidin-3-yl]pyridine (b-24-2) 3-[2,3-Dimethyl-5-(4-methylphenyl)isoxazolidin-3-yl]pyridine and (b-24-3) 3-[2-Isopropyl-3-methyl-5-(4-chlorophenyl)isoxazolidin-3-yl]pyridine 5 Group (25) a quinoline series compound selected from (b-25-1) Quinoxyfen (b-25-2) [6-(1,1-Dimethylethyl)-8-fluoro-2,3-dimethyl quinoline-4-yl] acetate and (b-25-3) [6-(1,1-Dimethylethyl)-8-fluoro-2,3-dimethyl quinoline-4-yl] methoxyacetate 10 Group (26) a thiazolidine series compound selected from (b-26-1) (2Z)-{[2-fluoro-5-(trifluoromethyl)phenyl]thio}[3-(2-methoxy phenyl)-1,3 thiazolidin-2-ylidene]acetonitrile and (b-26-2) (2Z)-{[2-fluoro-5-(trifluoromethyl)phenyl]thio}[3-(2-methylphenyl)-1,3-thiazolidin 15 2-ylidene]acetonitrile Group (27) a pyrazolinone series compound selected from (b-27-1) 1-
[(2-Propenylthio)carbonyl] -2- (1 -methylethyl)-4-(2-methylphenyl)-5 -amino-1H pyrazol-3-one 20 (b-27-2) 1- [(Ethylthio)carbonyl] -2- (1 -methylethyl)-4-(2-methylphenyl)-5 -amino-1 H-pyrazol
3-one and (b-27-3) 1- [(Ethylthio)carbonyl] -2- (1 -methylethyl)-4-(2,6-dichlorophenyl)-5 -amino-1H pyrazol-3-one and 25 Group (28) other fungicide- mildewcide selected from (b-28-1) Hydroxyisoxazol (b-28-7) Fenamidone (b-28-8) Chloropicrin 30 (b-28-9) Thiadiazine (b-28-10) Proquinazid (b-28-1 1) Spiroxamine (b-28-12) Fenpropidin (b-28-13) Dithianon - 91 (b-28-14) Pencycuron (b-28-15) Isoprothiolane (b-28-16) Probenazole (b-28-17) Resveratrol 5 (b-28-18) Triforine (b-28-19) Acibenzolar-S-methyl (b-28-20) Pyroquilon (b-28-21) Dinocap (b-28-22) Nickel bis(dimethyldithiocarbamate) 10 (b-28-23) Etridiazole (b-28-24) Oxadixyl (b-28-25) Amobam (b-28-26) Pyrifenox (b-28-27) Oxolinic acid 15 (b-28-28) Phosphorous acid (b-28-29) Dazomet (b-28-30) Methyl isothiocyanate (b-28-3 1) Methasulfocarb (b-28-32) 1,3-dichloropropene 20 (b-28-33) Carbam (b-28-34) Methyl iodide (b-28-35) Sulfur (b-28-36) Lime-sulfur mixed agent (b-28-37) Fentin 25 (b-28-38) Sodium hypochlorite (b-28-39) Chinomethionat (b-28-40) Chloroneb (b-28-41) Anilazine (b-28-42) Nitrothal-isopropyl 30 (b-28-43) Fenitropan (b-28-44) Dicloran and (b-28-45) Benthiazole as effective ingredients. - 92 2. A controlling method for controlling plant diseases by applying the plant disease control composition according to claim 1. 3. A method for controlling plant diseases, which comprises simultaneously applying a plant 5 disease control composition containing the quinoline compound of Group a according to claim 1 as an active ingredient and a plant disease control composition containing the fungicidal compound of Group b according to claim 1 as an active ingredient, or after applying either one of the plant disease control composition containing the compound of Group a according to claim 1 as an active ingredient or the plant disease control composition containing the 10 fungicidal compound of Group b according to claim 1 as an active ingredient, and then applying the other above-mentioned composition.
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