WO2015005355A1 - Synergistic plant disease-controlling composition comprising picolinic acid derivative - Google Patents

Abstract

The purpose of the present invention is to provide a plant disease-controlling composition or combination, said composition or combination comprising a picolinic acid derivative together with another plant disease-controlling agent. Provided is a plant disease-controlling composition or combination that comprises at least one member selected from among a compound represented by formula (I) [wherein R represents an isopropylcarbonyloxymethyl group, an acetyl group, an acetyloxymethyl group, an isobutyloxycarbonyl group or a benzo[d][1,3]dioxo-5-ylmethyl group], an enantiomer thereof, a mixture thereof or an agriculturally or horticulturally acceptable salt thereof together with at least one kind of other plant disease-controlling agent.

Description

Synergistic plant disease control composition comprising a picolinic acid derivative Reference to related applications

This patent application enjoys the benefits of Japanese Patent Application No. 2013-144633, which is a Japanese application filed on July 10, 2013. The entire disclosure of this earlier application is hereby incorporated by reference.

The present invention relates to a novel plant disease control composition or combination containing a picolinic acid derivative and at least one other plant disease control agent.

Many pest control agents have been found so far, but there are problems of reduced drug sensitivity, problems of sustaining effects, safety during use (for example, safety for workers), environment Due to safety in terms of impact, there is a need for new drugs that are still highly effective and highly safe. There is also a need for a control method that prevents plant pathogens from acquiring resistance and low sensitivity to drugs.

Patent Document 1 discloses a compound represented by the formula (I) of the present application, but there is no specific description regarding mixed use with other agents.

Patent Documents 2 and 3 show the control effect on wheat diseases by mixing with other agents of the compound represented by the formula (I) of the present application, respectively, but regarding the control of diseases such as vegetables and fruit trees, There is no description.

WO2003 / 035617 WO2011 / 044213 Publication WO2011 / 103240 gazette

The present inventors have found that a specific plant disease can be controlled synergistically by using a specific picolinic acid derivative in combination with another plant disease control agent. The present invention is based on this finding.

An object of the present invention is to provide a novel plant disease control composition or combination.

According to the present invention, the following inventions are provided.
[1] The following formula (I):

[Wherein, R represents an isopropylcarbonyloxymethyl group, an acetyl group, an acetyloxymethyl group, an isobutyloxycarbonyl group, or a benzo [d] [1,3] dioxo-5-ylmethyl group. ]
At least one of a compound represented by the following, an enantiomer thereof, or a mixture thereof, or an agriculturally and horticulturally acceptable salt thereof:
Group (II) consisting of the following (1) to (18):
(II)
(1) Nucleic acid synthesis inhibitor (2) Mitotic fission and cell division inhibitor (3) Complex I inhibitor (4) Complex II inhibitor (5) Complex III inhibitor (6) Oxidative phosphorylation Uncouplers (7) Oxidative phosphorylation inhibitors (8) ATP synthesis inhibitors (9) Amino acid and protein synthesis inhibitors (10) Signal transduction inhibitors (11) Lipid and cell membrane synthesis inhibitors (12) Membrane sterols Synthesis inhibitors (13) Cell wall biosynthesis inhibitors (14) Cell wall melanin synthesis inhibitors (15) Host plant resistance inducers (16) Multi-acting point contact activators (17) Plant disease control selected from Agent:
Simoxanyl, fosetyl, phosphorous acid, teclophthalam, triazoxide, fursulfamide, diclomedin, metasulfocarb, cyflufenamide, metolaphenone, pliophenone, dodin, flutolanil, ferrimzone, tebufloquine, oxathiapiproline, NNF-0721, MIF-1002, and NF- 171 and (18) Plant disease control agent selected from:
JP 2009-078991 A, JP 2009-073823 A, WO 2008/102678 A, JP 2010-083763 A, republished WO 2008/0666148, republished WO 2009/028280, WO 2005/115994. At least one plant disease control agent selected from the compounds described in JP-A-2006-290883, WO2007 / 072999, WO2007 / 108483, WO2008 / 062878, and WO2006 / 098128 A composition or combination for controlling plant diseases, comprising:
[2] A plant disease control agent selected from the group (II) is (3) complex I inhibitor, (4) complex II inhibitor, (5) complex III inhibitor, (10) signal transduction inhibition. A plant disease control composition or combination according to [1], selected from an agent, (12) a sterol synthesis inhibitor of membrane, and (17) tebufloquine.
[3] A plant disease control agent selected from the group (II) is diflumetrim, tolfenpyrad, benodanyl, flutolanil, mepronil, isophetamide, fluopyram, fenfram, carboxin, oxycarboxyl, tifluzamide, benzobindiflupyr, bixafen, full Xapiroxado, furametopir, isopyrazam, penflufen, penthiopyrad, sedaxane, boscalid, azoxystrobin, cumoxystrobin, enoxastrobin, fluphenoxystrobin, picoxystrobin, pyroxystrobin, pyraclostrobin, pyrame Tostrobin, Triclopyricarb, Cresoxime methyl, Trifloxystrobin, Dimoxystrobin, Phenaminostrobin, Metominostrobin, Orisastrobin, Fu Selected from moxadone, floxastrobin, mandestrobin, pyriminostrobin, phenamidon, pyribencarb, cyazofamide, amisulbrom, amethoctrazine, fludioxonil, epoxiconazole, fenbuconazole, metconazole, cimeconazole, and tebufloquine [1] The composition or combination for plant disease control as described in above.
[4] The following formula (I):

[Wherein, R represents an isopropylcarbonyloxymethyl group, an acetyl group, an acetyloxymethyl group, an isobutyloxycarbonyl group, or a benzo [d] [1,3] dioxo-5-ylmethyl group. ]
A composition for controlling plant diseases, comprising at least one of the compounds represented by the above, enantiomers thereof, mixtures thereof, or agriculturally and horticulturally acceptable salts thereof: Group (II) consisting of:
(II)
(1) Nucleic acid synthesis inhibitor (2) Mitotic fission and cell division inhibitor (3) Complex I inhibitor (4) Complex II inhibitor (5) Complex III inhibitor (6) Oxidative phosphorylation Uncouplers (7) Oxidative phosphorylation inhibitors (8) ATP synthesis inhibitors (9) Amino acid and protein synthesis inhibitors (10) Signal transduction inhibitors (11) Lipid and cell membrane synthesis inhibitors (12) Membrane sterols Synthesis inhibitors (13) Cell wall biosynthesis inhibitors (14) Cell wall melanin synthesis inhibitors (15) Host plant resistance inducers (16) Multi-acting point contact activators (17) Plant disease control selected from Agent:
Simoxanyl, fosetyl, phosphorous acid, teclophthalam, triazoxide, fursulfamide, diclomedin, metasulfocarb, cyflufenamide, metolaphenone, pliophenone, dodin, flutolanil, ferrimzone, tebufloquine, oxathiapiproline, NNF-0721, MIF-1002, and NF- 171 and (18) Plant disease control agent selected from:
JP 2009-078991 A, JP 2009-073823 A, WO 2008/102678 A, JP 2010-083763 A, republished WO 2008/0666148, republished WO 2009/028280, WO 2005/115994. At least one plant disease control agent selected from the compounds described in JP-A-2006-290883, WO2007 / 072999, WO2007 / 108483, WO2008 / 062878, and WO2006 / 098128 A composition for use in combination with.
[5] As an active ingredient, at least one compound represented by formula (I) defined in [1], an enantiomer thereof, a mixture thereof, or an agriculturally and horticulturally acceptable salt thereof; A method for controlling plant diseases comprising applying at least one plant disease control agent selected from the defined group (II) to the area to be treated, simultaneously or separately.
[6] The plant disease control composition or combination according to any one of [1] to [3] is used as a target pest, a target useful plant, a seedling of the target useful plant, a seed, a root, or a tuber of the target useful plant. A method for controlling plant diseases, which comprises applying to a bulb or rhizome, soil, or a cultivation carrier.
[7] Use of the plant disease control composition or combination according to any one of [1] to [3] for controlling plant diseases.
[8] A compound represented by the formula (I) defined in [1], an enantiomer thereof, a mixture thereof, or an agricultural and horticulturally acceptable product for producing a plant disease control composition or combination And a plant disease control agent selected from the group (II) defined in [1].

Detailed description of the invention

The picolinic acid derivative used in the present invention is a compound represented by the formula (I), an enantiomer thereof, a mixture thereof, or an agriculturally and horticulturally acceptable salt thereof (hereinafter referred to as “formula (I)”. Sometimes referred to as a picolinic acid derivative).

In the present invention, the compound represented by the formula (I) is specifically selected from the compounds A to E shown below.

The compound represented by the formula (I) is preferably the compound A described above.

Examples of the agriculturally and horticulturally acceptable salt of the compound represented by the formula (I), its enantiomer, or a mixture thereof include acid addition salts such as hydrochloride, sulfate, nitrate, phosphate and acetate.

In the present invention, the plant disease control agent used in combination with the picolinic acid derivative represented by the formula (I) is selected from the group (II) consisting of (1) to (18). (1) to (18) will be specifically described below.

(1) Nucleic acid synthesis inhibitors Examples of nucleic acid synthesis inhibitors include benalaxyl, benalaxyl-M (benalaxyl-M), furaxyl (furalaxyl), metalaxyl (metalaxyl), metalaxyl-M (metalaxyl-M), oxadixyl. (Oxadixyl), offurace, bupirimate, dimethirimol, ethirimol, hymexazole, octhilinone, oxolinic acid and the like.

(2) Mitotic fission and cell division inhibitor Examples of mitotic fission and cell division inhibitors include, for example, benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate, Examples include thiophanate-methyl, dietofencarb, zoxamide, ethaboxam, pencycuron, fluopicolide, and the like.

(3) Complex I inhibitor Examples of the complex I inhibitor include diflumetorim and tolfenpyrad.

(4) Complex II inhibitors Complex II inhibitors include, for example, benodanil, flutolanil, mepronil, isofetamid, fluopyram, fenfuram, carboxin (Carboxin), oxycarboxin, thifluzamide, benzovindiflupyr, bixafen, fluxapyroxad, furametpyr, isopyrazam, penflufen ), Penthiopyrad, sedaxane, boscalid and the like. The complex II inhibitor is preferably isofetamid, fluxapyroxad, furametpyr, penflufen, penthiopyrad, and boscalid, more preferably Isofetamid, fluxapyroxad, furametpyr, and penflufen.

(5) Complex III inhibitor Examples of the complex III inhibitor include azoxystrobin, coumoxystrobin, enoxastrobin, flufenoxystrobin, pico Xoxystrobin, pyraoxystrobin, pyraclostrobin, pyrametostrobin, triclopyricarb, cresoxim-methyl, trifloxystrobin , Dimoxystrobin, fenaminstrobin, metominostrobin, orysastrobin, famoxadone, fluoxastrobin, mandestrobin, pyriminosto Robin (pyriminostrobin), fenamidone (fenamidone), pyribencarb (pyribencarb), cyazofamid (cyazofamid), amisulbrom (amisulbrom), ametoctrazine (ametoctradin) and the like. The complex III inhibitor is preferably azoxystrobin, picoxystrobin, kresoxim-methyl, trifloxystrobin, metominostrobin, orisostrobin ( orysastrobin), famoxadone, fluoxastrobin, pyribencarb, cyazofamid, amisulbrom, ametoctradin, more preferably metinostrobin, orosminostrobin (Orysastrobin), famoxadone, fluoxastrobin, pyribencarb, cyazofamid, amisulbrom, amethoctrazine (ametoctradin).

(6) Uncoupling agent for oxidative phosphorylation Examples of the uncoupling agent for oxidative phosphorylation include binapacryl, meptyldinocap, dinocap, fluazinam and the like. .

(7) Oxidative phosphorylation inhibitor Examples of the oxidative phosphorylation inhibitor include fentin acetate, fentin chloride, fentin hydroxide, and the like.

(8) ATP synthesis inhibitor Examples of the ATP synthesis inhibitor include silthiofam.

(9) Amino acid and protein synthesis inhibitors As amino acid and protein synthesis inhibitors, for example, cyprodinil, mepanipyrim, pyrimethanil, blasticidin S (blasticidin-S), kasugamycin, Streptomycin, oxytetracycline, etc. are mentioned.

(10) Signal transduction inhibitor Examples of signal transduction inhibitors include quinoxyfen, proquinazid, fenpiclonil, fludioxonil, fludioxonil, chlozolinate, iprodione, and procymidone. , Vinclozolin and the like. The signaling inhibitor is preferably fludioxonil.

(11) Lipid and cell membrane synthesis inhibitors Examples of lipid and cell membrane synthesis inhibitors include edifenphos, iprobenfos, pyrazophos, isoprothione, biphenyl, chloroneb ( Examples include chloroneb, dicloran, quintozene, tecnazene, tolclofos-methyl, etridiazole, iodocarb, propamocarb, prothiocarb and the like.

(12) Membrane Sterol Synthesis Inhibitor Examples of the membrane sterol synthesis inhibitor include, for example, triforine, pyrifenox, pyrizoxazole, fenarimol, nuarimol, imazalil , Oxpoconazole, pefurazoate, prochloraz, triflumizole, azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole (Difenoconazole), diniconazole, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, Flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, microbutanil, penconazole, propiconazole, simeconazole , Tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, prothioconazole, aldimorph, dodemorph, phen Fenpropimorph, tridemorph, fenpropidin, piperalin, spiroxamine, fenhexamid, fenpyrazamine fenpyrazamine), pyributicarb (pyributicarb), naftifine (naftifine), terbinafine (terbinafine), and the like. The sterol synthesis inhibitor of the membrane is preferably epoxiconazole, fenbuconazole, metconazole, simeconazole, more preferably fenbuconazole, cimeconazole ( simeconazole).

(13) Cell wall biosynthesis inhibitor Cell wall biosynthesis inhibitors include, for example, validamycin, polyoxin, dimethomorph, flumorph, pyrimorph, and benchavalicarb. Iprovalicarb, valifenalate, mandipropamid and the like.

(14) Cell wall melanin synthesis inhibitor Cell wall melanin synthesis inhibitors include, for example, fthalide, pyroquilon, tricyclazole, carpropamid, diclocymet, fenoxanil, etc. Is mentioned.

(15) Host plant resistance inducer Examples of host plant resistance inducers include, for example, acibenzolar-S-methyl, probenazole, thiadinyl, isothianil, Laminarin etc. are mentioned.

(16) Multi-acting point contact activators Examples of multi-acting point contact activators include copper, sulfur, ferbam, mancozeb, maneb, metiram, Propineb, propirab, thiram, zineb, ziram, captan, captafol, folpet, chlorothalonil, dichlofluanid, tolylfluanid ), Guazatine, iminoctadine, anilazine, dithianon, quinoxaline (chinomethionat / quinomethionate), fluoroimide and the like.

(17) Other Examples of other plant disease control agents include, for example, cymoxanil, fosetyl-Al, phosphorous acid and salts, teclofthalam, triazoxide, and flusulfamide. ), Diclomezine, methasulfocarb, cyflufenamid, metrafenone, pyriofenone, dodine, flutolanil, ferimzone, tebufloquin, tebufloquin Examples include thiapiproline, NNF-0721, MIF-1002, and NF-171. Preferred is tebufloquin.

(18) Plant disease control agents shown below Examples of other plant disease control agents include JP2009-078991A, JP2009-073823A, WO2008 / 102678, JP2010 / 083763, Republished WO2008 / 066148, republished WO2009 / 028280, WO2005 / 115994, JP2006-290883, WO2007 / 072999, WO2007 / 108483, WO2008 / 062878, WO2006 / And compounds described in Japanese Patent No. 098128.

The plant disease control agent selected from the group (II) is preferably (3) complex I inhibitor, (4) complex II inhibitor, (5) complex III inhibitor, (10) signal transduction inhibition Agent, (12) sterol synthesis inhibitor of membrane, and (17) tebufloquine.

More preferably, the plant disease control agent selected from the group (II) is diflumetorim, tolfenpyrad, benodanil, flutolanil, mepronil, isofetamid, fluopyram fluopyram, fenfuram, carboxin, oxycarboxin, thifluzamide, benzovindiflupyr, benzovindiflupyr, bixafen, fluxapyroxad, furametpyr ), Isopyrazam, penflufen, penthiopyrad, sedaxane, boscalid, azoxystrobin, coumoxystrobin, enoxastrobin (eno) xastrobin), flufenoxystrobin, picoxystrobin, pyraoxystrobin, pyraclostrobin, pyrametostrobin, triclopyricarb, cresoxime methyl ( kresoxim-methyl, trifloxystrobin, dimoxystrobin, fenaminostrobin, metinominostrobin, orysastrobin, famoxadone, fluoxastrobin (Fluoxastrobin), mandestrobin, pyriminostrobin, fenamidone, pyribencarb, cyazofamid, amisulbrom, ametoctra Down (ametoctradin), fludioxonil (fludioxonil), epoxiconazole (epoxiconazole), fenbuconazole (fenbuconazole), is metconazole (metconazole), simeconazole (simeconazole), Tebufurokin (tebufloquin). Or diflumetorim, tolfenpyrad, benodanil, flutolanil, mepronil, isofetamid, fluopyram, fenfuram, carboxyxin, carboxin, (Oxycarboxin), thifluzamide, benzovindiflupyr, fluxapyroxad, furametpyr, penflufen, sedaxane, coumoxystrobin, enumoxystrobin Enoxastrobin, flufenoxystrobin, picoxystrobin, pyraoxystrobin, pyrametostrobin, triclopyrcarb (triclopyr) icarb), dimoxystrobin, phenaminostrobin, metominostrobin, orysastrobin, famoxadone, fluoxastrobin, mandestrobin , Pyriminostrobin, fenamidone, pyribencarb, cyazofamid, amisulbrom, ametoctradin, fludioxonil, fenbuconazole, fenbuconazole Tebufloquin.

More preferably, the plant disease control agent selected from the group (II) is diflumetorim, tolfenpyrad, isofetamid, fluxapyroxad, furametpyr, penflufen , Penthiopyrad, boscalid, azoxystrobin, picoxystrobin, kresoxim-methyl, trifloxystrobin, metominostrobin, orisatrobin (Orysastrobin), famoxadone, fluoxastrobin, pyribencarb, cyazofamid, amisulbrom, ametoctrazine, ametoctradin, fludioxonil (Fludioxonil), epoxiconazole, fenbuconazole, metconazole, simeconazole, tebufloquin.

The plant disease control agent selected from the group (II) is particularly preferably diflumetorim, tolfenpyrad, isofetamid, fluxapyroxad, furametpyr, penflufen , Metminostrobin, orysastrobin, famoxadone, fluoxastrobin, pyribencarb, cyazofamid, amethoctrazine, fludioxonil, fludioxonil, fludioxonil fenbuconazole), amisulbrom, simeconazole, tebufloquin.

According to the present invention, a plant disease control composition comprising at least one picolinic acid derivative represented by the formula (I) and at least one plant disease control agent selected from the group (II) Or a combination is provided. That is, the picolinic acid derivative represented by the formula (I) and the plant disease control agent selected from the group (II) can be provided as a composition or a combination.

In the present specification, the “plant disease control composition or combination” means a composition or combination exhibiting a synergistic control effect on plant diseases. Here, the protective effect includes not only killing the phytopathogenic microorganisms of the target plant disease, but also suppressing the growth of the phytopathogenic microorganisms and protecting the plant from being infected with the phytopathogenic microorganisms. Whether or not it has a synergistic protective effect can be determined by those skilled in the art according to a known method (for example, Colby's formula).

The composition or combination for controlling plant diseases of the present invention can be applied to vegetables, fruit trees, flowers, turf, and specifically, for example, tomato, pepper, eggplant, pepper, cucumber, pumpkin, watermelon , Melon, green beans, soybean, azuki bean, pea, broad bean, peanut, potato, sweet potato, sugar beet, rapeseed, radish, Chinese cabbage, broccoli, carrot, strawberry, leek, oyster, fig, banana, ume, sweet cherry, pear, peach, apple , Grapes, citrus, chrysanthemum, lily, tulip, cyclamen, sunflower, cosmos, crocus, freesia, shiba, turkey, bentgrass, etc., preferably tomato, cucumber, green beans, Chinese cabbage.

The plant disease control composition or combination of the present invention can also be applied to genetically modified crops and the like.

Examples of diseases in which the composition or combination for controlling plant diseases of the present invention exhibits a controlling effect include, for example, vegetable gray mold (Botrytis cinerea) such as tomato, cucumber, beans, strawberries, potatoes, cabbage, eggplant, lettuce, etc. , Tomatoes, cucumbers, beans, strawberries, potatoes, rapeseed, cabbage, eggplant, lettuce, etc., sclerotia sclerotia, tomatoes, cucumbers, beans, radish, watermelon, eggplant, rapeseed, peppers, spinach, sugar beet, etc. Vegetable seedling blight (Rhizoctonia spp., Phythium spp., Fusarium spp., Physophothora spp., Sclerotinia sclerotiorum, etc.), cucumber downy mildew (Pseudoperer) nospora cubensis), cucumber powdery mildew (Sphaerotheca furiginea), cucumber anthracnose (Colletotrichum lageniarum), cucumber vine disease (Dylymella bryoniae), Phytophthora melanis, Phytophthora nicotianae, Phytophthora drechsleri, Phytophthora capsici, etc., Tomato ring rot (Alternaria solifolia), Tomato leaf mold (Cladosporhumh) tans), tomato wilt disease (Phythium myriotylum), tomato anthracnose (Colletotrichoum phomosoids) Eggplant plague (Phytophthora infestans), eggplant brown rot (Phytophthora capsici), rape black spot (Alternaria brassicae), Brassicaceae black spot (Alternaria brassicae, etc.)朽病 (Leptospheria maculans), Brassicaceae clubroot (Plasmodiophora brassicae), Brassicaceae downy mildew (Peronospora brassicae)
Cabbage strain rot (Rhizoctonia solani), cabbage dwarf (Fusarium oxysporum), cabbage buttocks rot (Rhizoctonia solani), cabbage yellow rot (Verticillium dahlie) Leek white silkworm (Sclerotium rotsiii.), White leek white blight (Phytophthora umulity), Strawberry powdery rot (Sphaerotheca humulul) (Throw var.ultimum), soybean purpura (Cercospora kikuchii), soybean black scab (Elsinoe glycines), soybean sunspot (Diaporthe phaseolum), soybean rhizobonia rot (Rhizoctoniah) Downy mildew (Peronospora manchurica), Soybean rust (Phakopsora pachyrhizi), Soybean anthracnose (Colletotrichum pulmonata), Anthracnose (Colletotrichum lindemuthium pea) Brown spot disease (Cercospora arachidicola) Pea powdery mildew (Erysiphe pisi), pea downy mildew (Peronospora phijaia), black bean disease (Phytophathia rots) Rhizoctonia solani, potato epidemic (Phytophthora infestans), potato silver scab (Spandylocladium atrovirens), potato dry rot (Fusarium oxysporum), Fusarium sorghum spore nea), sugar beet brown spot (Cercospora beticola), sugar beet downy mildew (Peronospora schachtii), sugar beet black root disease (Aphanomyces cochioides), sugar beet blight (Phoma batai), grape rot a d Downy mildew (Plasmopora viticola), grape rust (Phakopsora ampelopsidis), grape powdery mildew (Uncinula necatoria), grape black rot (Elsinoe ampelina), grape late rot (Glomerella binga) ), Grape vine split disease (Phomopsis viti) ola), grape soot spot disease (Zygophiala jamaicensis), grape gray mold (Botrytis cinerea), grape shoot blight (Diaporthedium medusaea), grape purple leaf blight (Helicobasidium mompa), grape white crest wing Apple powdery mildew (Podosphaera leukotricha), apple black spot disease (Venturia inaequalis), apple spotted leaf disease (Alternaria alternari (Apple palamitype), apple red leaf disease (Gymnospora mellitus) Valsa ceratosperm a), Ringotropia berengeriana, Colletotrichum acutatum, Apple soot spot (Glyophiala maicaensis), Apple sop spot (Gloedodes pomigen) Diseases (Helicobasidium mompa), apple white coat disease (Rosellinia necatrix), apple head blight (Phomopsis mali), Diaporthe tanakae (Diplocarpon palae palae pal) , Pear scab ( Venturia nashicola), without gymnosporangium (Gymnosporangium haraeanum), without areolar disease (Physalospora piricola), pear blight (Diaporthe medusaea, Diaporthe eres), pears late blight (Phytophthora cactorum), peach scab (Cladosporium carpophilum), Momofomopushisu Spoilage disease (Phomopsis sp. ), Peach blight (Phytophthora sp.), Peach anthracnose (Gloeosporium laeticolor), sweet potato anthracnose (Glomelella kunuano), Monilinia kusanoi (Milinia kusanoi), Glooesporium kaki), oyster deciduous disease (Cercospora kaki, Mycosphaerella nawae), oyster powdery mildew (Phyllactinia kakikora), citrus black spot (Diaporthe citrus) Sick disease Elsinoe fawcettii, Chamochi rice rot (Exobasidium reticulatum), Cha white rot (Elsinoe leucospitala), Colletotrichoris teratotrophic disease, Tobacco powdery mildew (Erysiphe cichoracearum), Tobacco anthracnose (Colletotrichum tabacum), Tobacco plague (Phytophthora parasitetica), Cotton wilt (Fusarium oxysporum), Sunflower sclerotia iorum), rose black spot disease (Diplocarpon rosae), rose powdery mildew (Sphaerotheca pannosa), rose blight (Phytophthora megasperma), downy mildew (Peronospora sparsa) , Chrysanthemum rust (Puccinia horiana), chrysanthemum plague (Phytophthora cactorum), shiba brown patch disease (Rhizoctonia solani), Shivadarah spot disease (Sclerotinia homoeur ulva) Puccinia zoysiae), Shiva Helmint Sport Umm leaf blight (Cochliobolus sp. ), Rhynchosporium secalis, B. epidermis (Gaeumanomyces graminis), B. anthracnose (Colletotrichum graminicola), B. cerebellum (Typula incarnata) Ishikariensis), Shiba Snow rot large sclerotia nuclear disease (Sclerotinia borealis), Shiva Fairy ring (Marasumius oreades etc.), Shivapisium disease (Pythium aphanidermatum etc.), Shiva blast disease (Pyriculara etc.). Among these, resistance to drugs acting on the Qo site of cytochrome bc1 of complex protein III of mitochondrial electron transport system as described in Plant Protection No. 66, No. 9, pp. 481-487 (2012) And diseases showing resistance to drugs acting on the complex protein II of the mitochondrial electron transport system.

As a disease in which the composition for controlling plant diseases or the combination according to the present invention exhibits a controlling effect, preferably, vegetable gray mold (Botrytis cinerea), vegetable mycorrhizal disease (Sclerotinia sclerotiorum), cucurbitous powdery mildew ( Sphaerotheca filiginea), eggplant powdery mildew (Sphaerotheca fuliginea, etc.), strawberry powdery mildew (Sphaerotheca humuli), pea powdery mildew (Erysiphe pisci), grape powdery uinc Oyster powdery mildew (Phyllactinia kakikora), tobacco powdery mildew (Erysiphe cich) Racearum), is, more preferably, vegetables Botrytis (Botrytis cinerea), a Cucurbitaceae powdery mildew (Sphaerotheca fuliginea). Among these, resistance to drugs acting on the Qo site of cytochrome bc1 of complex protein III of mitochondrial electron transport system as described in Plant Protection, Vol. 66, No. 9, pp. 481-487 (2012) And diseases showing resistance to drugs acting on the complex protein II of the mitochondrial electron transport system.

The composition for controlling plant diseases of the present invention is selected from the group (II) and at least one of the compound represented by the formula (I), its enantiomer, or a mixture thereof, or an agriculturally and horticulturally acceptable salt thereof. In addition to at least one kind of plant disease control agent, it can be prepared using an agricultural and horticulturally acceptable carrier according to the usage.

The composition for controlling plant diseases of the present invention is usually mixed with an appropriate solid carrier, liquid carrier, gaseous carrier, surfactant, dispersant, other formulation adjuvants, emulsion, solution, suspension, It is provided in any dosage form such as wettable powder, flowable powder, powder, granule, fine granule F, microcapsule, tablet, oil, aerosol, smoke and the like. These various dosage forms can be produced by the method described in, for example, “Agricultural Chemicals Formulation Guide” (edited by the Japanese Agricultural Chemical Society / Application Method Research Group, published by the Japan Plant Protection Association, 1997).

Examples of the solid carrier include talc, bentonite, clay, kaolin, diatomaceous earth, vermiculite, white carbon, calcium carbonate and the like.

Examples of the liquid carrier include alcohols such as methanol, n-hexanol and ethylene glycol, ketones such as acetone, methyl ethyl ketone and cyclohexanone, aliphatic hydrocarbons such as n-hexane, kerosene and kerosene, toluene, xylene and methyl Aromatic hydrocarbons such as naphthalene, ethers such as diethyl ether, dioxane and tetrahydrofuran, esters such as ethyl acetate, nitriles such as acetonitrile and isobutyronitrile, acid amides such as dimethylformamide and dimethylacetamide, soybean Examples include vegetable oils such as oil and cottonseed oil, dimethyl sulfoxide, and water.

Examples of gaseous carriers include LPG, air, nitrogen, carbon dioxide, dimethyl ether and the like.

Surfactants and dispersants for emulsification, dispersion, spreading, etc. include, for example, alkyl sulfates, alkyl (aryl) sulfonates, polyoxyalkylene alkyl (aryl) ethers, polyhydric alcohol esters, A lignin sulfonate can be used.

For example, carboxymethyl cellulose, gum arabic, polyethylene glycol, calcium stearate and the like can be used as an adjuvant for improving the properties of the preparation.

The above carriers, surfactants, dispersants, and adjuvants can be used alone or in combination as necessary.

The content of the active ingredient in the preparation (that is, the total amount of the content of the picolinic acid derivative represented by the formula (I) and the content of the plant disease control agent selected from the group (II)) is particularly limited. Usually, it is 1 to 75% by weight for emulsions, 0.3 to 25% by weight for powders, 1 to 90% by weight for wettable powders, and 0.5 to 10% by weight for granules.

In the present invention, a mixing ratio of a picolinic acid derivative represented by the formula (I) and a plant disease control agent selected from the group (II) (picolinic acid derivative represented by the formula (I): selected from the group (II) Plant disease control agent) in a weight ratio of 1: 250 to 250: 1, preferably 1: 100 to 100: 1, more preferably 1:50 to 50: 1, even more preferably 1: It can be 25-25: 1. In the present invention, the ratio when the picolinic acid derivative represented by the formula (I) is combined with the plant disease control agent selected from the group (II) is also 1: 250 to 250: 1 by weight, preferably It can be 1: 100 to 100: 1, more preferably 1:50 to 50: 1, and even more preferably 1:25 to 25: 1.

As a plant disease control composition further comprising an agricultural and horticulturally acceptable carrier,
(1) 0.1 to 80% by weight of a picolinic acid derivative represented by the formula (I), 0.1 to 80% by weight of a plant disease control agent selected from the group (II), 0% of a wetting agent and a dispersing agent A composition in wettable powder form, containing from 6 to 30% by weight, and from 20 to 95% by weight of filler;
(2) 0.1 to 80% by weight of a picolinic acid derivative represented by the formula (I), 0.1 to 80% by weight of a plant disease control agent selected from the group (II), a wetting agent, a dispersing agent and a binding agent A composition in the form of a water dispersible granule containing 0.6 to 30% by weight of an agent and 20 to 95% by weight of a bulking agent;
(3) 0.1 to 80% by weight of a picolinic acid derivative represented by the formula (I), 0.1 to 80% by weight of a plant disease control agent selected from the group (II), a dispersant, a thickener, A composition in the form of a flowable comprising 5 to 40% by weight of a cryoprotectant, preservative and antifoam, and 20 to 94% by weight of water;
(4) 0.1 to 80% by weight of a picolinic acid derivative represented by the formula (I), 0.1 to 80% by weight of a plant disease control agent selected from the group (II), 1 emulsifier and emulsion stabilizer A composition in the form of an emulsion containing -30% by weight, 20-97% by weight of an organic solvent,
(5) 0.1 to 80% by weight of the picolinic acid derivative represented by the formula (I), 0.1 to 80% by weight of a plant disease control agent selected from the group (II), and 70 to 99. A composition in dust form containing at 8% by weight,
(6) 0.1 to 80% by weight of a picolinic acid derivative represented by the formula (I), 0.1 to 80% by weight of a plant disease control agent selected from the group (II), and 70 to 99.99% of a bulking agent. A composition which is in the form of a DL powder containing 8% by weight,
(7) 0.1 to 80% by weight of a picolinic acid derivative represented by the formula (I), 0.1 to 80% by weight of a plant disease control agent selected from the group (II), and 0.1% of a solvent or binder. A composition in the form of a fine granule F containing from 2 to 10% by weight, and from 70 to 99.6% by weight of an extender;
(8) 0.1 to 80% by weight of a picolinic acid derivative represented by the formula (I), 0.1 to 80% by weight of a plant disease control agent selected from the group (II), a granulating aid (surfactant) Agent) and a binder containing 0.5 to 30% by weight of a binder and 20 to 98% by weight of a bulking agent,
(9) 0.1 to 80% by weight of a picolinic acid derivative represented by the formula (I), 0.1 to 80% by weight of a plant disease control agent selected from the group (II), a coating agent, an emulsifier, and a dispersant And a composition in the form of a microcapsule containing 1 to 50% by weight of a preservative and 20 to 98% by weight of water. Preferably, it is a composition of (2), (3), (4).

The composition for controlling plant diseases according to the present invention comprises at least an active ingredient in the composition, the compound represented by formula (I), an enantiomer thereof, a mixture thereof, or an agriculturally and horticulturally acceptable salt thereof. It can be prepared by mixing one species and at least one plant disease control agent selected from the group (II). Alternatively, the composition for controlling plant diseases according to the present invention comprises a compound represented by the formula (I), an enantiomer thereof, a mixture thereof, or an agriculturally and horticulturally acceptable salt thereof, which is an active ingredient in the composition. And at least one kind of a plant disease control agent selected from the group (II) is prepared in advance and used in preparation of these preparations or dilutions thereof. You may mix and use a liquid on the spot.

According to another aspect of the present invention, the active ingredient is at least one compound of the formula (I), its enantiomer, or a mixture thereof, or an agricultural and horticulturally acceptable salt thereof, and a group ( II) A compound represented by formula (I), an enantiomer thereof, or a mixture thereof as an active ingredient by preparing at least one plant disease controlling agent selected from II) as a pharmaceutical form comprising each of them alone Or a combination comprising at least one of their agriculturally and horticulturally acceptable salts and at least one plant disease control agent selected from group (II).

For example, in the combination according to the present invention, the compound represented by formula (I), its enantiomer, or a mixture thereof, or an agriculturally and horticulturally acceptable salt thereof comprises the first composition comprising it as an active ingredient The plant disease control agent provided as a product and selected from the group (II) is provided as a second composition comprising it as an active ingredient. In this case, the first composition and the second composition are used in combination with an appropriate carrier, surfactant, dispersant, and other formulation adjuvants as in the case of the above-described plant disease control composition. Thus, any dosage form can be obtained. The combination according to the invention may be provided in the form of a drug set. The combination according to the invention may also be provided as a kit.

The plant disease control combination according to the present invention comprises at least one of the compounds represented by formula (I), an enantiomer thereof, or a mixture thereof, or an agriculturally and horticulturally acceptable salt thereof (for example, the first composition). And at least one plant disease control agent selected from the group (II) (for example, as the second composition) can be used simultaneously or sequentially. When using sequentially, either may be used first.

According to yet another aspect of the present invention, there is provided a method for controlling a plant disease, comprising at least a compound of formula (I), an enantiomer thereof, or a mixture thereof, or an agriculturally and horticulturally acceptable salt thereof. There is provided a method comprising applying one and at least one plant disease control agent selected from group (II) simultaneously or separately to the area to be treated.

In this method, to be applied "simultaneously" includes at least one compound of formula (I), an enantiomer thereof, or a mixture thereof, or an agrohortically acceptable salt thereof, and group (II) It is also included to apply the mixture after mixing with at least one plant disease control agent selected from before applying to the area to be treated. For “separately” application, without premixing them, at least one of the compounds of formula (I), their enantiomers, or mixtures thereof, or their agricultural and horticulturally acceptable salts can be applied. Applying prior to the other component and applying at least one of the compound of formula (I), its enantiomers, or mixtures thereof, or their horticulturally acceptable salts after the other component Is included.

According to still another preferred embodiment of the present invention,
(1) a first composition comprising, as an active ingredient, at least one of a compound represented by formula (I), an enantiomer thereof, a mixture thereof, or an agricultural and horticulturally acceptable salt thereof;
(2) Controlling a plant disease comprising applying a second composition comprising at least one plant disease control agent selected from the group (II) as an active ingredient to an area to be treated A method is provided.

According to another aspect of the present invention, the composition or combination of the present invention may be used as it is or diluted to apply pests (for example, phytopathogenic fungi), useful plants, seedlings of useful plants, useful plants. Can be applied to seeds, roots, tubers, bulbs or rhizomes, soil, or cultivating carriers, preferably useful plants, or soil to protect useful plants from pests and control plant diseases.

When applied to useful plants, spraying treatment is preferable, and the amount of active ingredient in the composition or combination of the present invention is preferably 0.1 g to 10 kg, preferably 1 g to 1 kg per 10 ares of cultivated land. .

In the case of treating seeds, roots, tubers, bulbs or rhizomes of useful plants, for example, a dipping method, a powder coating method, a smearing method, a spraying method, a pellet method, a film method, and a fumigation method can be mentioned.

The immersion method is a method in which seeds, roots, tubers, bulbs, or rhizomes are immersed in a liquid chemical solution. The powder coating method includes dry powder coating method in which a dry powder, tuber, bulb, or rhizome is attached to a powdered drug, and a light powder soaked seed, root, tuber, bulb, or rhizome in powder. There is a wet powder coating method to attach. The smearing method is a method in which a suspended drug is applied to the surface of seeds, tubers, bulbs or rhizomes in a mixer. The spraying method is a method of spraying a drug on the surface of seeds, roots, tubers, bulbs, or rhizomes. In the pellet method, seeds, tubers, bulbs, or rhizomes are pelletized together with a filler into a certain size and shape, and then the filling is mixed with a chemical. The film method is a method in which a film containing a drug is coated on seeds, tubers, bulbs or rhizomes. The fumigation method is a method of disinfecting seeds, roots, tubers, bulbs, or rhizomes with a gasified chemical in an airtight container. Preferable treatment methods include a dipping method, a powder coating method, a smearing method, a spraying method, a pellet method, and a film method.

The amount of treatment when applied to plant seeds, roots, tubers, bulbs or rhizomes is not particularly limited, but preferably the amount of active ingredient in the composition of the present invention is seeds, roots, tubers, bulbs or rhizomes. It is desirable to apply 1 g to 10 kg, more preferably 100 g to 1 kg per 100 kg.

When applied to seedlings of useful plants, it can be applied before transplanting by spraying treatment, water surface treatment, whole treatment by immersion or one part treatment.

When applying to soil, a granule containing the composition or combination of the present invention is applied to or on the soil, and a solution obtained by emulsifying or dissolving the composition or combination of the present invention in water is applied to the soil. Treatment or irrigation.

The amount of treatment of the composition or combination of the present invention to the soil is not particularly limited, but is preferably 0.1 g to 10 kg, preferably 1 g to 1 kg per 10 ares of cultivated land as an active ingredient.

When applied to a cultivation carrier, cultivation in a hydroponic system such as hydroponics and sand cultivation, NFT (Nutrient Film Technique), rock wool cultivation and the like for the production of vegetables and flowers Application to a liquid is mentioned, and it is preferable to apply a solution obtained by emulsifying or dissolving the composition or combination of the present invention in water by spraying or irrigating the soil.

According to the present invention, there is provided a method for protecting useful plants from pests (phytopathogenic fungi), which is a compound represented by formula (I) as an active ingredient, an enantiomer thereof, a mixture thereof, or an agricultural and horticulturally acceptable method thereof. Applying at least one possible salt and at least one plant disease control agent selected from group (II) simultaneously or separately (preferably simultaneously with each component) to the area to be treated Is provided. When applied at the same time, it is selected from the group (II) with at least one of the compounds represented by formula (I) as an active ingredient, enantiomers thereof, or a mixture thereof, or an agriculturally and horticulturally acceptable salt thereof. The at least one plant disease control agent may be applied as a composition or a combination.

According to another aspect of the present invention, there is provided use of the composition or combination for controlling plant diseases of the present invention for controlling plant diseases.

According to another aspect of the present invention, a compound represented by formula (I), an enantiomer thereof, or a mixture thereof, or an agricultural or horticultural basis thereof, for producing the plant disease control composition or combination of the present invention. There is provided the use of top acceptable salts and plant disease control agents selected from group (II).

In a preferred embodiment of the present invention, the following formula (I):

[Wherein, R represents an isopropylcarbonyloxymethyl group. ]
At least one of a compound represented by the following, an enantiomer thereof, or a mixture thereof, or an agriculturally and horticulturally acceptable salt thereof:
(3) Complex I inhibitor, (4) Complex II inhibitor, (5) Complex III inhibitor, (10) Signaling inhibitor, (12) Membrane sterol synthesis inhibitor, and (17) Tebufloquine A plant disease control composition or combination comprising at least one plant disease control agent selected from the group consisting of: Here, the plant disease is preferably vegetable gray mold or cucumber powdery mildew.

As a more preferred embodiment of the present invention, the following formula (I):

[Wherein, R represents an isopropylcarbonyloxymethyl group. ]
At least one of a compound represented by the following, an enantiomer thereof, or a mixture thereof, or an agriculturally and horticulturally acceptable salt thereof:
Diflumetorim, tolfenpyrad, benodanil, flutolanil, mepronil, isofetamid, fluopyram, fenfuram, carboxyxin, carboxin, oxin oxycarboxin, thifluzamide, benzovindiflupyr, bixafen, fluxapyroxad, furametpyr, isopyrazam, isopyrazam, penflufen, thio rad (Sedaxane), boscalid, azoxystrobin, coumoxystrobin, enoxastrobin, flufenoxystrobin, picoxy Trobin (picoxystrobin), pyraoxystrobin (pyraoxystrobin), pyraclostrobin (pyrametostrobin), triclopyricarb (triclopyricarb), cresoxim-methyl (kresoxim-methyl), trifloxystrobin (trifloxystrobin), dimomo Dimoxystrobin, fenaminostrobin, metominostrobin, orysastrobin, famoxadone, fluoxastrobin, mandestrobin, pyriminosto Robin (pyriminostrobin), fenamidone (pyamidone), pyribencarb (pyribencarb), cyazofamid (cyazofamid), amisulbrom (amisulbrom), ametoctrazine (ametoctradin), fludioxonil (fludioxonil), epoxycona Plant disease control comprising at least one plant disease control agent selected from epoxiconazole, fenbuconazole, metconazole, simeconazole, and tebufloquin It is a composition or combination. Here, the plant disease is preferably vegetable gray mold or cucumber powdery mildew.

As a more preferred embodiment of the present invention, the following formula (I):

[Wherein, R represents an isopropylcarbonyloxymethyl group. ]
At least one of a compound represented by the following, an enantiomer thereof, or a mixture thereof, or an agriculturally and horticulturally acceptable salt thereof:
Diflumetorim, tolfenpyrad, isofetamid, fluxapyroxad, furametpyr, penflufen, penthiopyrad, boscalid, azoxytrobin , Picoxystrobin, kresoxim-methyl, trifloxystrobin, metinominostrobin, orysastrobin, famoxadone, fluoxastrobin, pyribencarb (Pyribencarb), cyazofamid, amisulbrom, ametoctradin, fludioxonil, epoxiconazole, fenbuconazo A plant disease control composition or combination comprising at least one plant disease control agent selected from fenbuconazole, metconazole, simeconazole, and tebufloquin. Here, the plant disease is preferably vegetable gray mold or cucumber powdery mildew.

As a particularly preferred embodiment of the present invention, the following formula (I):

[Wherein, R represents an isopropylcarbonyloxymethyl group. ]
At least one of the compounds represented by the formula:
Diflumetorim, tolfenpyrad, isofetamid, fluxapyroxad, furametpyr, furametpyr, penflufen, metominostrobin, orosaastrobin, orysastrobin, orosastrobin Fluoxastrobin, pyribencarb, cyazofamid, cyazofamid, ametoctradin, fludioxonil, fenbuconazole, amisulbrom, simeconazole teflokin A plant disease control composition or combination comprising at least one selected plant disease control agent. Here, the plant disease is preferably vegetable gray mold or cucumber powdery mildew.

According to the present invention, the following inventions are also provided.
[1] Contains at least one picolinic acid derivative represented by the formula (I), an enantiomer thereof, a mixture thereof, or an acid addition salt thereof and at least one plant disease control agent represented by (II) A composition or combination for controlling plant diseases

[R represents an isopropylcarbonyloxymethyl group, an acetyl group, an acetyloxymethyl group, an isobutyloxycarbonyl group, or a benzo [d] [1,3] dioxo-5-ylmethyl group]
(II)
(1) Nucleic acid synthesis inhibitor (2) Mitotic fission and cell division inhibitor (3) Complex I inhibitor (4) Complex II inhibitor (5) Complex III inhibitor (6) Oxidative phosphorylation Uncoupling inhibitor (7) Oxidative phosphorylation inhibitor (8) ATP synthesis inhibitor (9) Amino acid and protein synthesis inhibitor (10) Signaling inhibitor (11) Lipid and cell membrane synthesis inhibitor (12) Membrane inhibitor Sterol synthesis inhibitors (13) Cell wall biosynthesis inhibitors (14) Cell wall melanin synthesis inhibitors (15) Host plant resistance induction inhibitors (16) Multi-acting point contact activators (17) Plant diseases selected from Control agents Cymoxanil, fosetyl-Al, phosphoric acid and salts, teclofthalam, triazoxide, trisulfoxide, disulfide Medlo (diclomezine), metasulfocarb (methasulfocarb), cyflufenamid (cyflufenamid), metrafenone (metrafenone), pyriofenone (pyriofenone), dodine (fludilil), ferrimzone (ferimzone), tebufloquine (tebufloquin), oxathiapi Proline (oxathiapiprolin), NNF-0721, MIF-1002, NF-171
(18) Plant disease control agent shown below JP2009-078991, JP2009-073823, WO2008 / 102678, JP2010-083763, republication WO2008 / 066148, republication WO2009 / 028280, WO2005 / 115994, special Compounds described in Open 2006-290883, WO2007 / 072999, WO2007 / 108483, WO2008 / 062878, WO2006 / 098128.
[2] An effective amount of the plant disease control composition or combination according to [1] is treated with the target pest, the target useful plant, the seed of the target useful plant, the soil, or the cultivation carrier. How to protect useful plants from pests.
[3] Use of the plant disease control composition or combination according to [1] for protecting useful plants from plant pathogens.

EXAMPLES Hereinafter, although an Example is given and this invention is demonstrated concretely, this invention is not limited to these Examples.
“Compound A” used in this example means a compound of the formula (I) in which R represents an isopropylcarbonyloxymethyl group.
[Formulation example]
Formulation Example 1 [wettable powder]
Compound A 10% by weight
Boscalid 20% by weight
50% by weight of clay
2% white carbon
Diatomaceous earth 13% by weight
Calcium lignin sulfonate 4% by weight
Sodium lauryl sulfate 1% by weight
The above ingredients were mixed uniformly and pulverized to obtain a wettable powder.

Formulation Example 2 [Granular wettable powder]
Compound A 10% by weight
Penthiopyrad 20% by weight
60% clay
Dextrin 5% by weight
Alkyl maleic acid copolymer 4% by weight
Sodium lauryl sulfate 1% by weight
The above components were uniformly pulverized and mixed, water was added and kneaded well, and then granulated and dried to obtain a granular wettable powder.

Formulation Example 3 [Flowable Agent]
Compound A 10% by weight
Azoxystrobin 20% by weight
POE polystyryl phenyl ether sulfate 5% by weight
Propylene glycol 6% by weight
Bentonite 1% by weight
Xanthan gum 1% aqueous solution 3% by weight
PRONALEX-300 (Toho Chemical Co., Ltd.) 0.05% by weight
ADDAC 827 (Kay Kasei Co., Ltd.) 0.02% by weight
100% by weight of water
The total amount excluding the 1% aqueous solution of xanthan gum and an appropriate amount of water from the above blend was premixed and then pulverized with a wet pulverizer. Thereafter, 1% aqueous solution of xanthan gum and the remaining water were added to obtain a flowable agent at 100% by weight.

Formulation Example 4 [Emulsion]
Compound A 10% by weight
Epoxyconazole 5% by weight
N, N-dimethylformamide 20% by weight
Solvesso 150 (ExxonMobil Co., Ltd.) 55% by weight
10% by weight of polyoxyethylene alkyl aryl ether
The above ingredients were uniformly mixed and dissolved to obtain an emulsion.

Formulation Example 5 [powder]
Compound A 1.5% by weight
Tebufloquine 1.5% by weight
60% clay
Talc 36% by weight
Calcium stearate 1% by weight
The said component was mixed uniformly and the powder agent was obtained.

Formulation Example 6 [DL powder]
Compound A 1% by weight
Tebufloquin 1% by weight
DL clay 95.5 wt%
2% white carbon
Light liquid paraffin 0.5% by weight
The said component was mixed uniformly and the powder agent was obtained.

Formulation Example 7 [Fine Granule F]
Compound A 1% by weight
Tebufloquin 1% by weight
Carrier 94% by weight
2% white carbon
Hyzol SAS-296 2% by weight
The said component was mixed uniformly and the powder agent was obtained.

Formulation Example 8 [Granule]
Compound A 2% by weight
Penfulfen 1% by weight
Bentonite 39% by weight
Talc 10% by weight
46% by weight clay
2% by weight calcium lignin sulfonate
The above components were pulverized and mixed uniformly, kneaded well with water, and granulated and dried to obtain granules.

Formulation Example 9 [Microcapsule]
Compound A 2% by weight
Boscalid 3% by weight
25% by weight of urethane resin
Emulsifying / dispersing agent 5% by weight
Preservative 0.2% by weight
64.8% by weight of water
A microcapsule was obtained by forming a urethane resin film on the surfaces of the compound particles represented by the chemical formula (I) and the imidacloprid particles by the interfacial polymerization method using the above components.

Formulation Example 10 (Granule)
Compound A 2% by weight
Probenazole 24% by weight
Sodium lauryl sulfate 1% by weight
Bentonite 2% by weight
Calcium stearate 1% by weight
2% by weight of PVA
68% by weight of clay
The above components were pulverized and mixed uniformly, kneaded well with water, and granulated and dried to obtain granules.

[Test example]
Test example 1
A mixture solution having a predetermined concentration of the compound represented by the formula (I) and the compound selected from the group (II) was prepared, and this was used as a spray solution. The petals of the green beans (variety Serena) on the first day of flowering were collected, 8 petals were arranged in a petri dish, and 5 mL of the spray solution was sprayed on the petals using a spray gun so as to be uniform. Naturally dried petals were suspended in water with conidia of Botrytis cinerea and spray-inoculated with a conidia suspension adjusted to 1 × 10 ⁴ cells / mL (2 mL per petri dish). . This was kept in a chamber at a temperature of 21 ° C. and a humidity of 100%, and the control value was calculated after 4 days. According to the following criteria, the strength of disease was visually determined using the elongation of hyphae formed on the petals as an index, and then the control value was calculated using Formula 1 and Formula 2 and shown in Table 1.

Strength of disease 0; no hyphal elongation 0.5; slight hyphae 1; clear hyphal elongation inhibition 2; hyphal elongation is observed, but hyphal elongation is inhibited compared to no treatment Accept 3; Recognize hyphal elongation equivalent to no treatment

Formula 1
Disease severity = (average value of disease intensity x 100) / 3
Formula 2
Control value = (Disease level of untreated area-Disease level of treated area) / Disease level of untreated area × 100
The control value expected when the mixture is sprayed is the control value X when the compound represented by (I) is sprayed alone and the control value Y when the compound selected from (II) is sprayed alone. It can be calculated from Colby's formula (Formula 3) (see Colby, SR Calculation of the synergistic and antagonistic response of herbicide combinations. Weeds 1967, 15, 20-22). If the actual control value reaches at least the expected control value, it can be determined to have a synergistic effect.
Formula 3
Expected control value = (X + Y)-XY / 100

In the same manner, Compound A and Isophetamide, Compound A and Floxapyroxad, Compound A and Framethopil, Compound A and Penflufen, Compound A and Picoxystrobin, Compound A and Cresoxime Methyl, Compound A and Trifloxystrobin, Compound A Results for and methminostrobin, Compound A and orissastrobin, Compound A and famoxadone, Compound A and pyribencarb, Compound A and cyazofamide, Compound A and amisulbrom, Compound A and amethoctrazine, Compound A and fluoxastrobin, Compound A and penthiopyrad Are shown in Table 2 and Table 3.

Test example 2
A mixture solution having a predetermined concentration of the compound represented by the formula (I) and the compound selected from the group (II) was prepared, and this was used as a spray solution. On the first true leaf of the cucumber (variety 4 leaves) 12 days after sowing, a spray solution of 0.5 mL per leaf was sprayed uniformly using a spray gun. The first true leaf foliar cucumber powdery mildew spores (Sphaerotheca fuliginea) was suspended in water, and 2 × 10 ³ cells / mL to become so adjusted spore suspension 1mL per pot which was naturally dried Inoculated by spraying. This was controlled in a greenhouse, 10 days after inoculation, the number of lesions formed on the first true leaf was counted, and the control value was calculated using Formula 1 and Formula 2, and shown in Table 4.
Formula 1
Control value = {1− (number of lesions in the drug-treated group / number of lesions in the drug-untreated group)} × 100
The control value expected when the mixture is sprayed is the control value X when the compound represented by the formula (I) is sprayed alone and the compound selected from the group (II). Y can be calculated by Colby's formula (formula 2) (see Colby, SR Calculation of the synergistic and antagonistic response of herbicide combinations. Weeds 1967, 15, 20-22). If the actual control value reaches at least the expected control value, it can be determined to have a synergistic effect.
Formula 2
Expected control value = (X + Y)-XY / 100

Claims (8)

1. The following formula (I):
   

   

   [Wherein, R represents an isopropylcarbonyloxymethyl group, an acetyl group, an acetyloxymethyl group, an isobutyloxycarbonyl group, or a benzo [d] [1,3] dioxo-5-ylmethyl group. ]
   At least one of a compound represented by the following, an enantiomer thereof, or a mixture thereof, or an agriculturally and horticulturally acceptable salt thereof:
   Group (II) consisting of the following (1) to (18):
   (II)
   (1) Nucleic acid synthesis inhibitor (2) Mitotic fission and cell division inhibitor (3) Complex I inhibitor (4) Complex II inhibitor (5) Complex III inhibitor (6) Oxidative phosphorylation Uncouplers (7) Oxidative phosphorylation inhibitors (8) ATP synthesis inhibitors (9) Amino acid and protein synthesis inhibitors (10) Signal transduction inhibitors (11) Lipid and cell membrane synthesis inhibitors (12) Membrane sterols Synthesis inhibitors (13) Cell wall biosynthesis inhibitors (14) Cell wall melanin synthesis inhibitors (15) Host plant resistance inducers (16) Multi-acting point contact activators (17) Plant disease control selected from Agent:
   Simoxanyl, fosetyl, phosphorous acid, teclophthalam, triazoxide, fursulfamide, diclomedin, metasulfocarb, cyflufenamide, metolaphenone, pliophenone, dodin, flutolanil, ferrimzone, tebufloquine, oxathiapiproline, NNF-0721, MIF-1002, and NF- 171 and (18) Plant disease control agent selected from:
   JP 2009-078991 A, JP 2009-073823 A, WO 2008/102678 A, JP 2010-083763 A, republished WO 2008/0666148, republished WO 2009/028280, WO 2005/115994. At least one plant disease control agent selected from the compounds described in JP-A-2006-290883, WO2007 / 072999, WO2007 / 108483, WO2008 / 062878, and WO2006 / 098128 A composition or combination for controlling plant diseases, comprising:
2. A plant disease control agent selected from group (II) is (3) complex I inhibitor, (4) complex II inhibitor, (5) complex III inhibitor, (10) signal transduction inhibitor, The composition or combination for plant disease control according to claim 1, selected from 12) a sterol synthesis inhibitor of a membrane, and (17) tebufloquine.
3. The plant disease control agent selected from the group (II) is diflumetrim, tolfenpyrad, benodanyl, flutolanil, mepronil, isophetamide, fluopyram, fenfram, carboxin, oxycarboxyl, tifluzamide, benzovindiflupyr, bixafen, fluxapiloxad , Furametopir, isopyrazam, penflufen, penthiopyrad, sedaxane, boscalid, azoxystrobin, cumoxystrobin, enoxastrobin, fluphenoxystrobin, picoxystrobin, pyroxystrobin, pyraclostrobin, pyramethostrobin, Triclopyricarb, Cresoxime methyl, Trifloxystrobin, Dimoxystrobin, Phenaminostrobin, Metominostrobin, Orisastrobin, Phas 2. Selected from oxadone, fluoxastrobin, mandestrobin, pyriminostrobin, phenamidon, pyribencarb, cyazofamide, amisulbrom, amethoctrazine, fludioxonil, epoxiconazole, fenbuconazole, metconazole, cimeconazole, and tebufloquine. The composition or combination for plant disease control as described in above.
4. The following formula (I):
   

   

   [Wherein, R represents an isopropylcarbonyloxymethyl group, an acetyl group, an acetyloxymethyl group, an isobutyloxycarbonyl group, or a benzo [d] [1,3] dioxo-5-ylmethyl group. ]
   A composition for controlling plant diseases, comprising at least one of the compounds represented by the above, enantiomers thereof, mixtures thereof, or agriculturally and horticulturally acceptable salts thereof: Group (II) consisting of:
   (II)
   (1) Nucleic acid synthesis inhibitor (2) Mitotic fission and cell division inhibitor (3) Complex I inhibitor (4) Complex II inhibitor (5) Complex III inhibitor (6) Oxidative phosphorylation Uncouplers (7) Oxidative phosphorylation inhibitors (8) ATP synthesis inhibitors (9) Amino acid and protein synthesis inhibitors (10) Signal transduction inhibitors (11) Lipid and cell membrane synthesis inhibitors (12) Membrane sterols Synthesis inhibitors (13) Cell wall biosynthesis inhibitors (14) Cell wall melanin synthesis inhibitors (15) Host plant resistance inducers (16) Multi-acting point contact activators (17) Plant disease control selected from Agent:
   Simoxanyl, fosetyl, phosphorous acid, teclophthalam, triazoxide, fursulfamide, diclomedin, metasulfocarb, cyflufenamide, metolaphenone, pliophenone, dodin, flutolanil, ferrimzone, tebufloquine, oxathiapiproline, NNF-0721, MIF-1002, and NF- 171 and (18) Plant disease control agent selected from:
   JP 2009-078991 A, JP 2009-073823 A, WO 2008/102678 A, JP 2010-083763 A, republished WO 2008/0666148, republished WO 2009/028280, WO 2005/115994. At least one plant disease control agent selected from the compounds described in JP-A-2006-290883, WO2007 / 072999, WO2007 / 108483, WO2008 / 062878, and WO2006 / 098128 A composition for use in combination with.
5. As defined in claim 1, an active ingredient is at least one compound of formula (I) defined in claim 1, its enantiomer, or a mixture thereof, or an agricultural and horticulturally acceptable salt thereof. A method for controlling plant diseases comprising applying at least one plant disease control agent selected from the group (II) to a region to be treated, simultaneously or separately.
6. A plant disease control composition or combination according to any one of claims 1 to 3, comprising a target pest, a target useful plant, a target useful plant seedling, a target useful plant seed, a root, a tuber, a bulb, Or the control method of a plant disease which comprises applying to a rhizome, soil, or a cultivation support | carrier.
7. Use of the plant disease control composition or combination according to any one of claims 1 to 3 for controlling plant diseases.
8. A compound represented by formula (I) as defined in claim 1, its enantiomer, or a mixture thereof, or an agriculturally and horticulturally acceptable salt thereof for producing a plant disease control composition or combination Use of a plant disease control agent selected from the group (II) defined in claim 1.