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    • 专利摘要:
    abstract the present invention provides a composition for controlling plant disease comprising a carboxamide compound represented by a formula (i): wherein r1 represents a hydrogen atom or a methyl group, and r2 represents a methyl group, a difluoromethyl group or a trifluoromethyl group; and a compound represented by a formula (a):, which has an excellent controlling activity on plant diseases. translation of the invention patent summary summary: "composition for plant disease control and application for it". the present invention relates to a plant disease control composition comprising a carboxamide compound represented by formula (i): where r1 represents a hydrogen atom or a methyl group, and r2 represents a methyl group, a methyl difluoro group or a trifluoro methyl group; and a compound represented by a formula (a): which has an excellent control activity against plant diseases.
    公开号:BR112015001121B1
    申请号:R112015001121-7
    申请日:2013-06-18
    公开日:2020-03-10
    发明作者:Yuichi Matsuzaki
    申请人:Sumitomo Chemical Company, Limited；
    IPC主号:
    专利说明:

    Descriptive Report of the Invention Patent for "COMPOSITION AND PROCESS FOR PLANT DISEASE CONTROL".
    Field of the Invention [0001] The present invention relates to a composition for controlling plant disease and an application for it.
    Background to the Technique [0002] Until now, some compounds have been developed to control plant disease and have been applied for practical use (see, for example, patent literature 1 and 2).
    Patent Literature 1: WO 86/02641 pamphlet Patent Literature 2: WO 92/12970 pamphlet Exposure of the Invention Technical Problem [0003] An object of the present invention is to provide a composition having excellent control effectiveness over plant disease.
    Technical Solution [0004] The present inventors studied intensively to find a composition having an excellent efficacy to control plant disease. As a result, they found that a composition comprising a carboxamide compound represented by a formula (I) and a compound represented by a formula (A) shows excellent control effectiveness over plant disease and therefore the present invention has been completed. The present invention provides: [0005] [1] A plant disease control composition comprising a carboxamide compound represented by a formula (I): where [0006] R1 represents a hydrogen atom or a methyl group, and [0007] R2 represents a methyl group, a methyl difluor group or a methyl trifluor group; and [0008] a compound represented by a formula (A): [0009] [2] The plant disease control composition described in [1] where a weight ratio of the carboxamide compound to the compound represented by the formula ( A) is that of the carboxamide compound / the compound represented by the formula (A) = 0.1 / 1 to 10/1.
    [0010] [3] A process for controlling plant disease comprising applying an effective amount of each of a carboxamide compound represented by a formula (I): where [0011] R1 represents a hydrogen atom or a group methyl, and [0012] R2 represents a methyl group, a methyl fluorine group or a methyl trifluor group; and the compound represented by formula (A): to a plant or soil for plant cultivation.
    [0013] [4] The process for controlling plant disease described in [3] where a weight ratio of the carboxamide compound to the compound represented by formula (A) is that of the carbo-xamide compound / the compound represented by formula ( A) = 0.1 / 1 to 10/1.
    [0014] [5] The process for controlling plant disease described in [3] or [4] where the plant or soil for plant cultivation is soy or soil for cultivation of soy.
    Modality for Carrying Out the Invention [0015] The plant disease control composition of the present invention (hereinafter referred to as "the present composition") comprises the carboxamide compound represented by formula (I): where R1 and R2 are the same as defined above (hereinafter, referred to as "present carboxamide compound") and the compound represented by formula (A): (hereinafter referred to as "present compound (A)").
    [0016] The present carboxamide compounds are those described in, for example, WO 86/02641 pamphlet and WO 92/12970 pamphlet, and thus can be prepared according to the process described there.
    [0017] The present carboxamide compound has an asymmetric carbon, and due to the asymmetric carbon, there are both enantiomers, that is, the (R) isomer represented by the formula (1-R): where R1 and R2 are the same as defined above, and the isomer (S) represented by the formula (1-S): where R1 and R2 are the same as defined above. In the present invention, the present carboxamide compound can be used as any mixture thereof in optional enantiomeric ratio.
    [0018] Specific examples of the present carboxamide compound include the following compounds: [0019] A carboxamide compound represented by formula (I): (hereinafter, referred to as "present carboxamide compound (1)"), [0020] a carboxamide compound represented by the formula (1R): (hereinafter referred to as "the present carboxamide compound (1R)"), [0021] a carboxamide compound represented by the formula (2): (hereinafter referred to as "the present carboxamide compound (2)" ), [0022] a carboxamide compound represented by the formula (2R): (hereinafter referred to as "the present carboxamide compound (2R)"), a carboxamide compound represented by the formula (3): (hereinafter referred to as "the present compound carboxamide (3) "), [0023] a carboxamide compound represented by the formula (3R): (hereinafter referred to as" the present carboxamide compound (3R) "), [0024] a carboxamide compound represented by the formula (4): ( hereinafter referred to as "present with carboxamide (4) "), and [0025] a carboxamide compound represented by formula (5): (hereinafter referred to as" the present carboxamide compound (5) "). [0026] The present compound (A) is a publicly known compound and is described, for example, in WO 02/10101 pamphlet. The present compound (A) can be prepared according to the known process.
    [0027] Here, the present compound (A) has an asymmetric carbon, and due to the asymmetric carbon, there are both enantiomers, that is, the (R) isomer represented by the formula (A1): and the (S) isomer represented by the formula (A2): [0028] In the present invention, the present compound (A) can be used as any of its mixtures in optional enanthiomeric ratio. Enantiomers can be prepared according to the process described in WO 02/10101.
    [0029] The weight ratio of the present carboxamide compound to the present compound (A) in the present composition is, for example, that of the present carboxamide compound / the present compound (A) = 0.01 / 1 to 500/1, preferably 0.1 / 1 to 10/1, and more preferably 0.5 / 1 to 1/7.
    [0030] Although the present composition may be a mixture in itself of the present carboxamide compound and the present compound (A), and the present composition is usually prepared by mixing the present carboxamide compound, the present compound (A) and a carrier inert, and if necessary, adding a surfactant or other pharmaceutical additives, and then formulating it in the form of an oily solution, emulsifiable concentrate, flowable formulation, moistable spray, granular wet spray, powder formulation, granules and so on. Such formulations can be used by themselves or with an addition of other inert components such as an agent for controlling plant disease.
    [0031] Usually, the present composition may contain 0.1 to 99% by weight, preferably 0.2 to 90% by weight, and more preferably 1 to 80% by weight of the present carboxamide compound and the present compound (A) in total.
    [0032] Examples of a solid carrier used in the formulation include powdered or finely divided clay particles consisting of minerals (eg, kaolin clay, atapulgite clay, bento-nita, montmorillonite, acid clay, pyrophyllite, talc, diatomaceous earth, or calcite ), natural organic substances (for example, sprayed with corn cob, or sprayed with nutshells), synthetic organic substances (for example, urea), salts (for example, calcium carbonate, or ammonium sulphate), substances synthetic inorganic (for example, synthetic hydrated silicon oxide) and so on. Examples of a liquid carrier include aromatic hydrocarbons (for example, xylene, alkyl benzene, or methyl naphthalene), alcohols (for example, 2-propanol, ethylene glycol, propylene glycol, or ethylene glycol mono ethyl ether), ketones (for example, acetone, hexanone cycle, or isophorone), vegetable oils (for example, soybean oil, or cottonseed oils), petroleum-derived aliphatic hydrocarbons, esters, dimethyl sulfoxide, acetonitrile and water.
    [0033] Examples of the surfactant include anionic surfactant (for example, alkyl sulfate salts, alkyl aryl sulfonate salts, dialkyl sulfo succinate salts, polyoxyethylene alkyl aryl ether phosphate, lignin sulfonate, or polycondensation of naphthalene sulfonate formaldehyde), non-ionic surfactant (for example, polyoxyethylene alkyl aryl ether, polyoxyethylene alkyl poloioxypropylene block copolymer, or sorbitan fatty acid ester) and cationic surfactant (for example, trimethyl ammonium salts).
    [0034] Examples of the other pharmaceutical additives include water-soluble polymer (eg, polyvinyl alcohol, or polyvinyl pyrrolidone), polysaccharides (eg, arabic gum, alginic acid and its salts, CMC (carboxy methyl cellulose), or gum xanthan), inorganic substances (eg magnesium aluminum silicate, or sol-alumina), antiseptic agent, coloring agent, and PAP (isopropyl acid phosphate), and stabilizing agent (eg BHT).
    [0035] The present composition can also be prepared by means of a separate formulation of the present carboxamide compound and the present compound (A) in different formulations using the procedures mentioned above, if necessary, further diluting each of them with water, afterwards, mixing the different formulations prepared separately comprising the present carboxamide compound or the present compound (A), or the solutions diluted with each other.
    [0036] The present composition can be used to prevent plant disease.
    [0037] The plant disease that can be controlled by the present composition is exemplified below: [0038] Rice diseases: mangra (Magnaporthe grisea), brown spot (Cochliobolus miyabeanus), sheath rust (Rhizoctonia solani), and bakanae disease ( Gibberella fujikuroi);
    [0039] Wheat diseases: pulverized mildew (Erysiphe graminis), fusarium mangrove (Fusarium gaminearum, F. avenaceum, F. culmorum, Microdochium nivale), rust (Puccinia striiformis, P. graminis, P. recondita), snow mold ( Micronectriella nivale), typhula snow mangrove (Typhula sp.), Loose soot (Ustilago tritici), fetid soot (Til-letia caries), eye-shaped spot (Pseudocercosporella herpotri-choides), leaf spot (Mycosphaerella graminicola), gluma spot (Stagonospora nodorum), and brown spot (Pyrenophora tritici-repentis);
    [0040] Barley diseases: downy downy mildew (Erysiphe graminis), loose soot (Fusarium gaminearum, F. avenacerum, F. culmorum, Microdochium nivale), rust (Puccinia striiformis, P. graminis, P. hordei) loose soot (Ustilago nuda) ), burn (Rhynchosporium secalis), pure spot (Pyrenophora teres), spot spot (Co-chliobolus sativus), leaf stripe (Pyrenophora gramínea), and damping-off caused by rhizoctonia fungus (Rhizoctonia solani);
    [0041] Corn diseases: soot (Ustilago maydis), southern leaf mangrove (Cochliobolus heterostrophus), zoned leaf spot (Gloeocercospora sorghi), southern rust (Puccinia polysora), gray leaf spot (Cercospora zeae-maydis) , and damping-off caused by the rhizoctonia fungus (Rhizoctonia solani);
    [0042] Citrus diseases: melanosis (Diaporthe citri), crust (Elsi-noe fawcetti), common green mold (Penicillium digitatum), blue mold (P. italicum) and Phytophthora disease, brown rot (Phytophthora pa-rasítica, Phytophthora citrophthora );
    [0043] Apple diseases: flowering plague (Monilinia mali), cancer (Waltz ceratosperm); downy downy mildew (Podosphaera leuco-tricha), leaf spot Alternaria (patotype apple Alternaria alternata), crust (Venturia inaequalis), bitter rot (Colletotrichum acuta-tum), and colon rot (Phytophtora cactorum);
    [0044] Pear diseases: crust (Venturia nashicola, V. pirina), black spot (pear pathotype Alternaria alternate Japanese), rust (Gymnosporangium haraeanum), and colon rot and Phytophthora root (Phytophthora cactorum);
    [0045] Peach diseases: brown rot (Monilinia fructico-la), crust (Cladosporium carpophilum), and Phomopsis rot (Phomopsis sp.);
    [0046] Grape diseases: anthracnose (Elsinoe ampelina), ripe rot (Glomerella cingulata), pulverized mildew (Uncinula necator), rust (Phakopsora ampelopsidis), black rot (Guignardia bidwellii) and downy mildew (Plasmopara);
    [0047] Japanese persimmon diseases: anthracnose (Gloeosporiura ka-ki), and leaf point (Cercospora kaki, Mycosphaerella nawae);
    [0048] Cucurbitaceae diseases: anthracnose (Colletotrichum la-genarium), pulverized mildew (Sphaerotheca fuliginea), viscous trunk disease (Mycosphaerella melonis), withered Fusarium (Fusarium oxysporum), downy mildew (Pseudisyphosphorhystophthysphyrusporthusphystophylphyrusporthyrophosphorphyrustophthysphyrophysporytophthysphyrophysporytophthysphyrophysporytophthysphylphyrustophthysphylphyrustophthysphylphyrustophthysphyrophysporytophthysphyrysporthyrophosthyphosphorphyrustophthysphyrophysporytophthysphyrysporthyrophosthyphosphyrustophthysphylphyrustophthysphylphyrusphyrustophthysphylphyrusphyrusporthustophthusphyrustophylum .), and damping-off (Pythium sp.);
    [0049] Tomato diseases: initial disease (Alternaria solani), leaf mold (Cladosporium fulvum), and late disease (Phytophthora infestans);
    [0050] Eggplant diseases: brown spot (Phomopsis vexans), and powdery mildew (Erysiphe cichoracearum);
    [0051] Diseases of the Brassica family: leaf spot of Alternaria (Alternaria japônica), white spot (Cercosporella brassicae), foal (Plasmodiophora brassicae), and downy mildew (parasitic peronospora);
    [0052] Welsh onion diseases: rust (Puccinia allii), and downy mildew (Peronospora destructor);
    [0053] Soy diseases: purple spot (Cercospora kikuchii), Sphaceloma chicharro (elsinoe glycines), stem and pod disease (Diaporthe phaseolorum var. Soye), brown septoria spot (Septo-glycines), Cercospora leaf spot ( Cercospora sojina), rust (Phakopsora pachyrhizi), stem and root rot phytophthora (Phytophthoraoyae), damping-off caused by rhizoctonia fungus (Rhi-zoctonia solani), target spot (Corynespora casiicola), and sclerum rotinia (sclerum rotinia) );
    [0054] Kindney bean diseases: leaf spot (Cercospora personata), brown leaf spot (Cercospora arachidicola), and southern disease (Sclerotium rolfsii);
    [0055] Garden pea diseases: powdery mildew (Erysiphe pisi);
    [0056] Potato diseases: initial mangrove (Alternari solani), late mangrove (Phytophthora infestans), pink rot (Phytophthora erythro-septica), and pulverized crust (Spongospora subterranean f. Sp. Subterraneous);
    [0057] Strawberry diseases: powdery mildew (Sphaerotheca humuli), and anthracnose (Glomerella cingulata);
    [0058] Tea diseases: liquid bubble spot (Exobasidium reticulatum), white crust (Elsinoe leucospila), gray mangrove (Pesta-lotiopsis sp.), And anthracnose (Colletotrichum theae-sinensis);
    [0059] Tobacco diseases: brown spot (Alternatia longipes), powdery mildew (Erysiphe cichoracearum), anthracnose (Colleto-trichum tabacum), downy mildew (Peronospora tabacina), and black stem (Phytophthora nicotianae);
    [0060] Rapeseed diseases: sclerotinia rot (Sclerotinia sclero-tiorum), and rapeseed damping-off caused by Rhizoctonia solani (Rhizoctonia solani);
    [0061] Cotton diseases: cotton seed rot caused by Rhizoctonia solani (Rhizoctonia solani);
    [0062] Sugar beet diseases: leaf spot of porpoise (Cercospora beticola), leaf mangrove (Thanatephorus cucume-ris), root rot (Thanatephorus cucumeris), and aphanomyces root rot (Aphanidermatum cochlioides);
    [0063] Rose diseases: black spot (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa), and downy mildew (Peronospo-ra sparsa);
    [0064] Vegetable diseases Crysanthemum and Asteraceae: downy mildew (Bremia lactucae), leaf mangrove (Septoria chrysanthemi-indici), and rust (Puccinia horiana);
    [0065] Various plant diseases: diseases caused by Pythium spp. (Pythium aphanidermatum, Pythium debarianum, Pythium grami-nicola, Pythium irregulare, Pythium ultimum), gray mold (Botrytis cine-rea), and Sclerotinia rot (Sclerotinia sclerotiorum);
    [0066] Japanese radish diseases: leaf spot of Alternaria (Alternaria brassicicola);
    [0067] Lawn diseases: dollar bill (Sclerotinia homeocar-pa), brown plaque, and large plaque (Rhizoctonia solani);
    [0068] Banana diseases: Sigatoka disease (Mycosphaerella fi-jiensis, Mycosphaerella musicola);
    [0069] Sunflower diseases: downy mildew (Plasmopara hals-tedii);
    [0070] Seed diseases or diseases in the early stages of growth of various plants caused by bacteria from Aspergillus spp., Penicillium spp., Fusarium spp., Gibberella spp., Tricoderma spp., Thielaviopsis spp., Rhizopus spp., Mucor spp ., Corticium spp., Phoma spp., Rhizoctonia spp., Diplodia spp .;
    [0071] Viral diseases of various plants mediated by the genus Polymixa or genus Olpidium.
    [0072] Examples of the plants to which the composition of the present invention can be applied are as follows: [0073] Crops: corn, rice, wheat, barley, rye, oats, sorghum, cotton, soy, peanuts, buckwheat, beet, rapeseed, sunflower, sugar cane, and tobacco, etc .;
    [0074] Vegetables: solanaceous vegetables (eggplant, tomato, pepper, and potato, etc.), cucurbitaceous vegetables (cucumber, pumpkin, zucchini, watermelon, melon, and pumpkin, etc.), crucifferous vegetables (Japanese radish, white turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, mustard, broccoli, and cauliflower, etc.), asteraceous vegetables (burdock, crown daisy, artichoke, and lettuce, etc.), liliaceous vegetables (welsh onion, onion, garlic, and asparagus), ammiaceous vegetables (carrots, parsley, celery, and parsnips, etc.), chenopodiaceous vegetables (spinach, Swiss chard, etc.), lamiaeous vegetables (perilla, mint, and basil, etc.), strawberry, potato sweet, glutinous yam, and taro, etc .;
    [0075] Flowers;
    [0076] Foliage plants;
    [0077] Lawns;
    [0078] Fruits: pomaceous fruits (apple, pear, Japanese pear, Chinese quince, and quince, etc.), pulpy stone fruits (peach, plum, nectarine, Japanese apricot (Prunus mume), cherry, apricot, and plum dried, etc.), citrus fruits (Citrus unshiu, orange, lemon, lime, and grapefruit, etc.), nuts (chestnut, walnuts, almonds, pistachios, cashew nuts, and macadamia nuts, etc.), berries (vací-nio, cranberry, blackberry, and raspberry, etc.), grapes, Japanese persimmon, olive, Japanese plum, banana, coffee, date palm, and coconuts, etc .; and [0079] Trees other than fruit trees: tea, mulberry, flowering plants, roadside trees (ash, birch, dogwood, eucalyptus, ginkgo (ginkgo biloba), lilac, maple, oak (quercus), mo, Judas tree, Formosan gum (Liquidambar formosana), flat tree, zelkova, Japanese arborvitae (Thuja standishii), spruce, hemlock, juniper, pine, spruce, and yew (Taxus cuspidate)), etc.
    [0080] The "plants" mentioned above include plants whose resistance was provided by genetic recombination.
    [0081] Among the above, in particular, a high control effect against plant diseases that occur in soybeans is expected.
    [0082] In addition, among plant diseases occurring in these crops, examples of soybean diseases for which a particularly high control effect is expected include sowing decay caused by rhizoctonia fungus (Rhizoctonia solani), purple seed spot (Cercospora kikuchii) , brown spot septoria (Septo-ria glycines), rust (Phakopsora pachyrhizi, sclerotinia rot (Sclerotinia sclerotiorum) and leaf spot (Cercospora sojina) and so on.
    [0083] Exemplary embodiments of the present composition are as follows: [0084] a composition comprising the present carboxamide compound (1) and the present compound (A);
    [0085] a composition comprising the present carboxamide compound (1R) and the present compound (A);
    [0086] a composition comprising the present carboxamide compound (2) and the present compound (A);
    [0087] a composition comprising the present carboxamide compound (2R) and the present compound (A);
    [0088] a composition comprising the present carboxamide compound (3) and the present compound (A);
    [0089] a composition comprising the present carboxamide compound (3R) and the present compound (A);
    [0090] a composition comprising the present carboxamide compound (4) and the present compound (A);
    [0091] a composition comprising the present carboxamide compound (5) and the present compound (A);
    [0092] a composition comprising the present carboxamide compound (1), etaboxam and the present compound (A);
    [0093] a composition comprising the present compound carboxamide (1R) m, etaboxam and the present compound (A);
    [0094] a composition comprising the present carboxamide compound (2), etaboxam and the present compound (A);
    [0095] a composition comprising the present carboxamide compound (2R), etaboxam and the present compound (A);
    [0096] a composition comprising the present carboxamide compound (3), etaboxam and the present compound (A);
    [0097] a composition comprising the present carboxamide compound (3R), etaboxam and the present compound (A);
    [0098] a composition comprising the present carboxamide compound (4), etaboxam and the present compound (A);
    [0099] a composition comprising the present carboxamide compound (5), etaboxam and the present compound (A);
    [00100] a composition comprising the present carboxamide compound (1), metalaxyl and the present compound (A);
    [00101] a composition comprising the present carboxamide compound (1R), metalaxyl and the present compound (A);
    [00102] a composition comprising the present carboxamide compound (2), metalaxyl and the present compound (A);
    [00103] a composition comprising the present carboxamide compound (2R), metalaxyl and the present compound (A);
    [00104] a composition comprising the present carboxamide compound (3), metalaxyl and the present compound (A);
    [00105] a composition comprising the present carboxamide compound (3R), metalaxyl and the present compound (A);
    [00106] a composition comprising the present carboxamide compound (4), metalaxyl and the present compound (A);
    [00107] a composition comprising the present carboxamide compound (5), metalaxyl and the present compound (A);
    [00108] a composition comprising the present carboxamide compound (1), metalaxyl M and the present compound (A);
    [00109] a composition comprising the present carboxamide compound (1R), metalaxyl M and the present compound (A);
    [00110] a composition comprising the present carboxamide compound (2), metalaxyl M and the present compound (A);
    [00111] a composition comprising the present carboxamide compound (2R), metalaxyl M and the present compound (A);
    [00112] a composition comprising the present carboxamide compound (3), metalaxyl M and the present compound (A);
    [00113] a composition comprising the present carboxamide compound (3R), metalaxyl M and the present compound (A);
    [00114] a composition comprising the present carboxamide compound (4), metalaxyl M and the present compound (A);
    [00115] a composition comprising the present carboxamide compound (5), metalaxyl M and the present compound (A);
    [00116] a composition comprising the present carboxamide compound (1), clothianidim and the present compound (A);
    [00117] a composition comprising the present compound carboxamide (1R), clothianidim and the present compound (A);
    [00118] a composition comprising the present carboxamide compound (2), clothianidim and the present compound (A);
    [00119] a composition comprising the present carboxamide compound (2R), clothianidim and the present compound (A);
    [00120] a composition comprising the present carboxamide compound (3), clothianidim and the present compound (A);
    [00121] a composition comprising the present carboxamide compound (3R), clothianidim and the present compound (A);
    [00122] a composition comprising the present carboxamide compound (4), clothianidim and the present compound (A);
    [00123] a composition comprising the present carboxamide compound (5), clothianidim and the present compound (A);
    [00124] a composition comprising the present carboxamide compound (1), imidacloprid and the present compound (A);
    [00125] a composition comprising the present carboxamide compound (1R), imidacloprid and the present compound (A);
    [00126] a composition comprising the present carboxamide compound (2), imidacloprid and the present compound (A);
    [00127] a composition comprising the present carboxamide compound (2R), imidacloprid and the present compound (A);
    [00128] a composition comprising the present carboxamide compound (3), imidacloprid and the present compound (A);
    [00129] a composition comprising the present carboxamide compound (3R), imidacloprid and the present compound (A);
    [00130] a composition comprising the present carboxamide compound (4), imidacloprid and the present compound (A);
    [00131] a composition comprising the present carboxamide compound (5), imidacloprid and the present compound (A);
    [00132] a composition comprising the present carboxamide compound (1), ipconazole and the present compound (A);
    [00133] a composition comprising the present compound carboxamide (1R), ipconazole and the present compound (A);
    [00134] a composition comprising the present carboxamide compound (2), ipconazole and the present compound (A);
    [00135] a composition comprising the present carboxamide compound (2R), ipconazole and the present compound (A);
    [00136] a composition comprising the present carboxamide compound (3), ipconazole and the present compound (A);
    [00137] a composition comprising the present carboxamide compound (3R), ipconazole and the present compound (A);
    [00138] a composition comprising the present carboxamide compound (4), ipconazole and the present compound (A);
    [00139] a composition comprising the present carboxamide compound (5), ipconazole and the present compound (A);
    [00140] a composition comprising the present carboxamide compound (1), metconazole and the present compound (A);
    [00141] a composition comprising the present carboxamide compound (1R), metconazole and the present compound (A);
    [00142] a composition comprising the present carboxamide compound (2), metconazole and the present compound (A);
    [00143] a composition comprising the present carboxamide compound (2R), metconazole and the present compound (A);
    [00144] a composition comprising the present carboxamide compound (3), metconazole and the present compound (A);
    [00145] a composition comprising the present carboxamide compound (3R), metconazole and the present compound (A);
    [00146] a composition comprising the present carboxamide compound (4), metconazole and the present compound (A);
    [00147] a composition comprising the present carboxamide compound (5), metconazole and the present compound (A);
    [00148] a composition comprising the present carboxamide compound (1), 4-oxo-4 - [(2-phenyl ethyl) amino] butyric acid and the present compound (A);
    [00149] a composition comprising the present carboxamide compound (1R), 4-oxo-4 - [(2-phenyl ethyl) amino] butyric acid and the present compound (A);
    [00150] a composition comprising the present carboxamide compound (2), 4-oxo-4 - [(2-phenyl ethyl) amino] butyric acid and the present compound (A);
    [00151] a composition comprising the present carboxamide compound (2R), 4-oxo-4 - [(2-phenyl ethyl) amino] butyric acid and the present compound (A);
    [00152] a composition comprising the present carboxamide compound (3), 4-oxo-4 - [(2-phenyl ethyl) amino] butyric acid and the present compound (A);
    [00153] a composition comprising the present carboxamide compound (3R), 4-oxo-4 - [(2-phenyl ethyl) amino] butyric acid and the present compound (A);
    [00154] a composition comprising the present carboxamide compound (4), 4-oxo-4 - [(2-phenyl ethyl) amino] butyric acid and the present compound (A);
    [00155] a composition comprising the present carboxamide compound (5), 4-oxo-4 - [(2-phenyl ethyl) amino] butyric acid and the present compound (A);
    [00156] a composition comprising the present carboxamide compound (1), tolclofos - methyl and the present compound (A);
    [00157] a composition comprising the present compound carboxamide (1R), tolclofos-methyl and the present compound (A);
    [00158] a composition comprising the present carboxamide compound (2), tolclofos - methyl and the present compound (A);
    [00159] a composition comprising the present compound carboxamide (2R), tolclofos-methyl and the present compound (A);
    [00160] a composition comprising the present carboxamide compound (3), tolclofos - methyl and the present compound (A);
    [00161] a composition comprising the present carboxamide compound (3R), tolclofos-methyl and the present compound (A);
    [00162] a composition comprising the present carboxamide compound (4), tolclofos - methyl and the present compound (A);
    [00163] a composition comprising the present carboxamide compound (5), tolclofos-methyl and the present compound (A);
    [00164] a composition comprising the present compound carboxamide (1), clothianidim, etaboxam, metalaxyl Meo the present compound (A);
    [00165] a composition comprising the present carboxamide compound (1R), clothianidim, etaboxam, metalaxyl M and the present compound (A);
    [00166] a composition comprising the present compound carboxamide (2), clothianidim, etaboxam, metalaxyl M and the present compound (A);
    [00167] a composition comprising the present compound carboxamide (2R), clothianidim, etaboxam, metalaxyl M and the present compound (A);
    [00168] a composition comprising the present compound carboxamide (3), clothianidim, etaboxam, metalaxyl M and the present compound (A);
    [00169] a composition comprising the present compound carboxamide (3R), clothianidim, etaboxam, metalaxyl M and the present compound (A);
    [00170] a composition comprising the present compound carboxamide (4), clothianidim, etaboxam, metalaxyl Meo the present compound (A);
    [00171] a composition comprising the present compound carboxamide (5), clothianidim, etaboxam, metalaxyl Meo the present compound (A);
    [00172] a composition comprising the present compound carboxamide (1), imidacloprid, etaboxam, metalaxyl M and the present compound (A);
    [00173] a composition comprising the present compound carboxamide (1R), imidacloprid, etaboxam, metalaxyl M and the present compound (A);
    [00174] a composition comprising the present compound carboxamide (2), imidacloprid, etaboxam, metalaxyl M and the present compound (A);
    [00175] a composition comprising the present carboxamide compound (2R), imidacloprid, etaboxam, metalaxyl M and the present compound (A);
    [00176] a composition comprising the present compound carboxamide (3), imidacloprid, etaboxam, metalaxyl M and the present compound (A);
    [00177] a composition comprising the present compound carboxamide (3R), imidacloprid, etaboxam, metalaxyl M and the present compound (A);
    [00178] a composition comprising the present compound carboxamide (4), imidacloprid, etaboxam, metalaxyl M and the present compound (A);
    [00179] a composition comprising the present compound carboxamide (5), imidacloprid, etaboxam, metalaxyl M and the present compound (A);
    [00180] a composition comprising the present carboxamide compound (1) and the present compound (A) where a weight ratio thereof is that of the present carboxamide compound (1) / the present compound (A) = 0.1 / 1 a 10/1;
    [00181] a composition comprising the present carboxamide compound (1R) and the present compound (A) where a weight ratio thereof is that of the present carboxamide compound (1) / the present compound (A) = 0.1 / 1 a 10/1;
    [00182] a composition comprising the present carboxamide compound (2) and the present compound (A) where a weight ratio thereof is that of the present carboxamide compound (2) / the present compound (A) = 0.1 / 1 a 10/1;
    [00183] a composition comprising the present carboxamide compound (2R) and the present compound (A) where a weight ratio of them is that of the present carboxamide compound (2) / the present compound (A) = 0.1 / 1 a 10/1;
    [00184] a composition comprising the present carboxamide compound (3) and the present compound (A) where a weight ratio thereof is that of the present carboxamide compound (3) / the present compound (A) = 0.1 / 1 a 10/1;
    [00185] a composition comprising the present carboxamide compound (3R) and the present compound (A) where a weight ratio thereof is that of the present carboxamide compound (3) / the present compound (A) = 0.1 / 1 a 10/1;
    [00186] a composition comprising the present carboxamide compound (4) and the present compound (A) where a weight ratio thereof is that of the present carboxamide compound (4) / the present compound (A) = 0.1 / 1 a 10/1;
    [00187] a composition comprising the present carboxamide compound (5) and the present compound (A) where a weight ratio thereof is that of the present carboxamide compound (5) / the present compound (A) = 0.1 / 1 a 10/1;
    [00188] The plant disease control process of the present invention (hereinafter referred to as "the present invention control process") is carried out by applying an effective amount of each of the present carboxamide compound and the present compound (A) to a plant or soil for plant cultivation. Examples of such a plant include foliage from a plant, seeds from a plant and bulbs from a plant. In addition, the bulbs described here mean discoid stems, corms, rhizomes, tubers, tubers, and tuberous roots.
    [00189] In the control process of the present invention, the present carboxamide compound and the present compound (A) can be applied separately to a plant or soil for plant cultivation in the same period, but are usually applied as the composition of the present invention in terms of application convenience.
    [00190] In the control process of the present invention, examples of the process of applying the present carboxamide compound and the present compound (A) include foliage treatment, soil treatment, root treatment and seed treatment.
    [00191] Such foliage treatment includes, for example, a process of applying the composition of the present invention to the surface of a plant to be cultivated through foliar application or an application to the trunk.
    [00192] Such soil treatment includes, for example, sowing of soil, incorporation into the soil, and irrigation of the medicinal solution into a soil.
    [00193] Such a root treatment includes, for example, a process of soaking all or one root of the plant in a medicinal solution comprising the present carboxamide compound and the present compound (A), and a binding process of a solid formulation comprising the present carboxamide compound, the present compound (A) and the carrier to a plant root.
    [00194] Such a seed treatment includes, for example, an application of the composition of the present invention to a seed or a plant bulb to be prevented from plant disease, specifically, for example, spreading treatment by spreading a suspension of the composition of the present invention in a mist form on the surface of a seed or on the surface of a bulb, smear treatment through application of moisturizing spray, the emulsifiable concentrate or flowable formulation of the composition of the present invention with small amounts of water added or as itself to a seed or bulb, immersion treatment by immersing a seed in a solution of the composition of the present invention for a certain period of time, treatment of film coating by film coating of a mixture of the composition of the present invention and polymer on a semen surface te, and pellet coating treatment by formulating a mixture of the composition of the present invention and sprayed on pellet as nuclear seeds.
    [00195] Each dose of the present carboxamide compound and the present compound (A) in the process for controlling the present invention can be varied depending on the type of plant to be treated, a type or frequency of an occurrence of a plant disease such as control object, a dosage form, a treatment period, a treatment process, a treatment site, a climate condition, etc. In case of application to a plant foliage or a soil for plant cultivation, a total amount of the present carboxamide post and the present compound (A) is usually 1 to 500 g, preferably 2 to 200 g, and more preferably 10 at 100 g per 1000 m2. Each dose of the present carboxamide compound and the present compound (A) in the seed treatment is usually 0.001 to 10 g, and preferably 0.01 to 1 g, per 1 kg of seeds.
    [00196] The emulsifiable concentrate, the wet powder or the flowable formulation, etc., is usually applied by diluting them with water, and then spreading them. In this case, usually, each concentration of the present carboxamide compound and the present compound (A) contains 0.0005 to 2% by weight, and preferably 0.005 to 1% by weight of the present carboxamide compound and the present compound (A) in total. The powder formulation or granular formulation, etc., is usually applied as itself without diluting them.
    Examples [00197] In the following, the present invention is described in more detail below by Reference Preparation Examples, Formulation Examples and Test Examples.
    [00198] Reference Examples of the present carboxamide compound (1R), the present carboxamide compound (2R) and the present carboxamide compound (3R) are indicated below.
    Reference Preparation Example 1 [00199] To a solution of (R) -1,1,3-trimethyl-4-amino indane (optical purity 99% ee) 0.15 g, triethyl amine 0.13 g, 4- dimethyl amino pyridine 5 mg and THF 1 ml a solution of 0.17 g of 1-methyl-3-difluoro methyl pyrazol-4-carboxylic acid chloride in THF under ice cooling was added dropwise. The mixture was stirred at room temperature for fifteen minutes, and to the reaction mixture, ice water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated sodium chloride solution successively, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to yield amide (R) - (-) - N- (1,1,3-trimethyl indan-4-yl) -1-methyl-3-difluoro pyrazole -4-carboxylic (hereinafter referred to as "present carboxamide compound (2)) 0.20 g (99% ee optical purity).
    [00200] Present carboxamide compound (2) 1H-NMR (CDCl3) δ: 1.25 (3H, s), 1.28 (3H, d, J = 7.1 Hz), 1.34 (3H, s) , 1.67 (1H, dd, J = 12.9, 4.1 Hz), 2.24 (1H, dd, J = 12.9, 8.5 Hz), 3,323.41 (1H, m), 3.94 (3H, s), 6.88 (1H, t, J = 54.1 Hz), 6.98 (1H, d, J = 7.6 Hz), 7.22-7.27 (1H , m), 7.79 (1h, d, J = 7.8 Hz), 7.96 (1H, br s), 8.02 (1H, s).
    [a] D23 = -62o (CHCl3, c 0.99) Example Preparation Reference 2 [00201] To a solution of (R) -1,1,3-trimethyl-4-amino indane (99% ee optical purity) 0.15 g, triethyl amine 0.13 g, 4-dimethyl amino pyridine 5 mg and THF 1 ml a solution of 0.18 g 1-methyl-3-trifluoro methyl pyrazol-4-carboxylic acid chloride was added dropwise in THF under ice cooling. The mixture was stirred at room temperature for fifteen minutes, and to the reaction mixture, ice water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and a saturated solution of sodium chloride successively, dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to yield amide (R) - (-) - N- (1,1,3-trimethyl indan-4-yl) -1-methyl-3-trifluoro methyl pyrazole- 4-carboxylic (hereinafter referred to as "present carboxamide compound (1)) 0.18 g (99% ee optical purity).
    [00202] Present carboxamide compound (1) 1H-NMR (CDCl3) δ: 1.25 (3H, s), 1.28 (3H, d, J = 7.1 Hz), 1.34 (3H, s) , 1.67 (1H, dd, J = 12.8, 4.3 Hz), 2.24 (1H, dd, J = 12.9, 8.5 Hz), 3,293.37 (1H, m), 3.99 (3H, s), 7.00 (1H, d, J = 6.8 Hz), 7.23-7.27 (1H, m), 7.62 (1H, br s), 7, 76 (1H, d, J = 7.8 Hz), 8.04 (1H, s).
    [00203] [a] D23 = -54o (CHCl3, c 1.02) Example Preparation Reference 3 [00204] To a solution of (R) -1,1,3-trimethyl-4-amino indane (optical purity 99% ee) 0.15 g, triethyl amine 0.13 g, 4-dimethyl amino pyridine 5 m and 1 ml THF 1 ml was added dropwise a solution of 1,3,5-trimethyl pyrazole-4-carboxylic acid chloride g in THF under ice cooling. The mixture was stirred at room temperature for fifteen minutes, and to the reaction mixture, ice water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated sodium chloride solution successively, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was purified by chromatography on a silica gel column to yield amide (R) - (-) - N- (1,1,3-trimethyl indan-4-yl) -1,3,5-trimethyl pyrazole-4 -carboxylic (hereinafter referred to as "present carbo-xamide compound (3)) 0.17 g (99% ee optical purity).
    [00205] Present carboxamide compound (3) 1H-NMR (CDCl3) δ: 1.25 (3H, s), 1.32 (3H, d, J = 7.1 Hz), 1.34 (3H, s) , 1.67 (1H, dd, J = 12.7, 4.6 Hz), 2.24 (1H, dd, J = 12.9, 8.5 Hz), 2.51 (3H, s), 2.53 (3H, s), 3.31-3.39 (1H, m), 3.76 (3H, s), 6.96 (1H, d, J = 7.6 Hz), 7.21 -7.26 (2H, m), 7.76 (1H, d, J = 7.8 Hz).
    [a] D23 = -57o (CHCl3, c 1.01) [00206] Next, the preparation of an intermediate for the preparation of the present carboxamide compound is indicated.
    Preparation Example reference 4 [00207] Using an HPLC process, a 1,1,3-trimethyl-4-amino indane racemate 4.8 g was separated into each of its optical isomers under the following condition to obtain (R) - 1,1,3-trimethyl-4-amino indane 1.2 g (99% ee optical purity).
    Column: CHIRACEL (trademark) optically active column OD
    Column temperature: room temperature Mobile phase: a mixed solvent of hexane and 2-propanol (99: 1) Flow rate: 10 mL / minute [00208] (R) -1, 1,3-trimethyl-4-amino indane Preparation Example Reference 5 [00209] A 1,1,3-trimethyl-4-amino indane racemate 300 g, D-tartaric acid 128 g and methanol 260 ml was mixed and the mixture was kept at 60 ° C for 1 hour. Then the mixture was allowed to cool to room temperature, and the mixture was mixed with about 0.1 g of seed crystal, and the mixture was left to stand for two days. The formed solids were filtered and washed with methanol. The resulting solids were recrystallized five times from methanol to yield 100 g 1,1,3-trimethyl-4-amino indane D-tartaric acid salt. To the 1,1,3-trimethyl-4-amino indane D-tartaric acid salt 78 g, a 5% aqueous solution of sodium hydroxide was added to bring the pH to 10 or more, and the mixture was extracted with methyl t- butyl ether three times. The resulting oily layer was washed with saturated sodium chloride solution and saturated aqueous sodium hydrogen carbonate solution successively and then dried over sodium sulfate and concentrated under reduced pressure to yield a mixture of 1,1,3-trimethyl-4- amino indane 38 g in an enantiomeric ratio of the R / isAomer S isomer of 99.6 / 0.4.
    [00210] In addition, the Formulation Examples of the present composition are indicated. Here, "parts" means "parts by weight". Formulation Example 1 [00211] Two and a half parts (2.5) of any of the present carboxamide compounds (1) to (5), 1.25 parts of the present compound (A), 14 parts of sterile polyoxyethylene phenyl ether, 6 parts of calcium salt of dodecyl benzene sulfonic acid and 76.25 parts of xylene are finely mixed to obtain each formulation.
    Formulation Example 2 [00212] Two (2) parts of any of the present carboxamide compounds (1) to (5), 8 parts of the present compound (A), 35 parts of a mixture of white carbon and polyoxyethylene alkyl ether sulfate salt of ammonium (weight ratio 1: 1), and 55 parts of water are mixed and the resulting solution is then subjected to fine grinding according to a wet grinding process to obtain each formulation.
    Formulation Example 3 [00213] Five (5) parts of any of the present carboxamide compounds (1) to (5), 10 parts of the present compound (A), 1.5 parts of sorbitan trioleate and 28.5 partsd of solution aqueous solution containing 2 parts of polyvinyl alcohol are mixed, and the resulting solution is then subjected to a fine grinding process and 45 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of silicate are added to it magnesium aluminum, followed by the addition of 10 parts of propylene glycol, and the mixture is combined by stirring to obtain each formulation.
    Formulation Example 4 [00214] One (1) part of the present carboxamide compounds (1) to (5), 4 parts of the present compound (A), 1 part of synthetic hydrated silicon oxide, 2 parts of ligne calcium sulfonate, 3 parts of bentonite and 62 parts of kaolin clay are entirely crushed and mixed, and the resulting mixture is added with water and thoroughly kneaded, and then subjected to granulation and drying to obtain each formulation.
    Formulation Example 5 [00215] Twelve and a half parts (12.5) of any of the present carboxamide compounds (1) to (5), 37.5 parts of the present compound (A), 3 parts of ligne calcium sulfonate, 2 parts of sodium laurel sulfate and 45 parts of synthetic hydrated silicon oxide are completely crushed and mixed to obtain each formulation.
    Formulation Example 6 [00216] Three (3) parts of the present carboxamide compounds (1) to (5), 2 parts of the present compound (A), 85 parts of kaolin clay and 10 parts of talc are entirely crushed and mixed to obtain of each formulation.
    [00217] Still, Test examples are indicated.
    Test Example 1 [00218] One hundred (100) microliters of hexane solution containing predetermined weights of a test compound were applied to 10 g of soybean seeds (cultivar; natto-shoryu) using a rotary seed treatment machine (seed dresser , produced by Hans-Ulrich Hege GmbH).
    [00219] One (1) day after the above treatment, a plastic pot was filled with soil contaminated with rhizoctonia fungus (Rhizoctonia solani), and the seeds treated with the test compound were sown and grown in a glass greenhouse for twenty days ( which is defined as "treated group"). Then, the presence or absence of the beginning of seed rot caused by the rhizoctonia fungus (Rhizoctonia solani) was observed in a germinated nursery plant of each seed and the incidence rate was then calculated using the following equation (1).
    [00220] Separately, soybean seeds without the above seed treatment were grown similarly to the treated group (which is defined as "untreated group"). The incidence rate was calculated similarly to the treated group.
    [00221] Here, the carboxamide compound represented by formula (I) used in Example Test 1 and the present compound (A) using in Example Test 1 were used in a racemic mixture, respectively. [00222] From each of the incidence rates of the treated and untreated groups, the efficacy of the treated group was calculated using the following equation (2). The results are shown in Table 1 and Table 2.
    [00223] Incidence rate (%) = the number of germinated nursery plants / the total number of nursery plants x 100 (Equation (1)) [00224] Effectiveness (%) = (1 - incidence rate of the treated group / incidence rate of untreated group) x 100 (Equation (2)) Table 1 [Table 2] Example Test 2 [00225] A plastic pot was filled with soil and soybeans (cultivar; natto-shoryu) and the plants were grown in a greenhouse for fourteen (14) days. A test compound was dissolved in a CEC cocktail (hexane cycle: Sorpol (trademark) 2680X (Toho Chemical Industry Co. Ltd.) = 5: 1 (volume ratio), and the resulting mixture was formulated in an emulsifiable concentrate containing the test compound in 5% (weight / volume) in total and diluted with water to a predetermined concentration, and the diluted solution was applied by spraying on the soybean to adhere entirely on the leaf surfaces of the above soybeans. they were air dried and inoculated by spraying an aqueous suspension of soybean rust urediniospores (Phakopsora pachyrhizi) (about 10,000 / ml) 1 day after treatment.
    [00226] In initial times after inoculation, the plants were grown at 20 to 23oC in a humid condition for 1 day, and grown in a greenhouse for an additional 10 days (hereinafter referred to as "treated group"). Then, the area of lesion of soybean rust (Pha-kopsora pachyrhizi) was evaluated.
    [00227] Meanwhile, soybeans were grown similarly to the treated group except that no application to the foliage of the diluted solution above the test compound (hereinafter referred to as "untreated group"). The lesion area of soybean rust (Phakopsora pachyrhizi) was evaluated similarly to the treated group.
    [00228] Here, the carboxamide compound represented by formula (I) used in Example Test 2 and the compound represented by formula (A) used in Example Test 2 were used in racemic mixture, respectively.
    [00229] From each injury area of the treated group and the untreated group, the efficacy of the treated group was calculated using the following equation (3). The results are shown in Table 3 and Table 4.
    Effectiveness (%) = (1 - area of injury of the treated group / area of injury of the untreated group) x 100 (Equation (3)) [Table 3] '' [Table 4] '' Example Test 3 [00230] One hundred (100) microliters of hexane cycle solution containing predetermined weights of a test compound are applied through 10 g of soybean seeds (cultivar; natto-shoryu) using a rotary seed treatment machine (seed dresser, produced by Hans-Ulrich Hege GmbH).
    [00231] One (1) day after the above treatment, a plastic pot is filled with soil contaminated with fungorhizoctonia (Rhizoctonia so-lani), and the seeds treated with the test compound were sown and grown in a glass greenhouse for twenty days (which is defined as a "treated group"). Next, the presence or absence of the beginning of seed rot caused by the rhizoctonia fungus (Rhizoctonia solani) is observed in a germinated nursery plant for each seed and the incidence rate is then calculated using the following equation (4).
    [00232] Separately, soybean seeds without the above seed treatment were grown similarly to the treated group (which is defined as "untreated group"). The incidence rate is calculated similarly to the treated group.
    [00233] Here, the carboxamide compound represented by formula (I) used in Test Example 3 is used in a mixture of R: isomer S: 80:20 to 100: 0, more preferably R: isomer S: 95: 5 to 99: 1. Also, the present compound (A) used in Example Test 3 is used in a racemic mixture.
    [00234] From each of the incidence rates of the treated group and the untreated group, the efficacy of the treated group is calculated using the following equation (5).
    [00235] Incidence rate (%) = the number of germinated nursery plants / the total number of nursery plants x 100 (Equation (4)) Effectiveness (%) = (1 - incidence rate of the treated group / rate of incidence of untreated group) x 100 (Equation (5)) [Industrial Applicability] [00236] The present invention allows a plant to prevent plant diseases.
    权利要求:
    Claims (3)
    [1]
    1. Plant disease control composition characterized by comprising a carboxamide compound represented by a formula (1): a compound represented by a formula (A): where a weight ratio of the carboxamide compound represented by formula (1) to compound represented by formula (A) is that of the carboxamide compound represented by formula (1) / the compound represented by formula (A) = 0.1 / 1 to 10/1.
    [2]
    2. Plant disease control process characterized by the fact that it comprises the application of an effective amount of each of a carboxamide compound represented by formula (1): as defined in claim 1; and the compound represented by formula (A): as defined in claim 1 to a plant or soil for plant cultivation, wherein a weight ratio of the carboxamide compound represented by formula (1) to the compound represented by formula (A) be that of the carboxamide compound represented by formula (1) / the compound represented by formula (A) = 0.1 / 1 to 10.1.
    [3]
    3. Plant disease control process according to claim 2, characterized in that the plant is soy or the soil for cultivating soy.
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    法律状态:
    2018-03-06| B06F| Objections, documents and/or translations needed after an examination request according art. 34 industrial property law|
    2018-03-13| B06F| Objections, documents and/or translations needed after an examination request according art. 34 industrial property law|
    2018-03-20| B06I| Technical and formal requirements: publication cancelled|Free format text: ANULADA A PUBLICACAO CODIGO 6.6.1 NA RPI NO 2462 DE 13/03/2018 POR TER SIDO INDEVIDA. |
    2019-04-09| B07A| Technical examination (opinion): publication of technical examination (opinion)|
    2020-01-07| B09A| Decision: intention to grant|
    2020-03-10| B16A| Patent or certificate of addition of invention granted|Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 18/06/2013, OBSERVADAS AS CONDICOES LEGAIS. |
    优先权:
    申请号 | 申请日 | 专利标题
    JP2012-161709|2012-07-20|
    JP2012161709A|JP6106976B2|2012-07-20|2012-07-20|Plant disease control composition and use thereof|
    PCT/JP2013/067160|WO2014013842A1|2012-07-20|2013-06-18|Composition for controlling plant disease and application therefor|
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