JP2009096734A - Amide compound and application for controlling plant disease - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a compound exhibiting excellent controlling activity against a plant disease. <P>SOLUTION: The amide compound represented by formula (I) exhibits the excellent controlling activity against the plant disease. The amide compound is useful as an active ingredient of the controlling agent against the plant disease. <P>COPYRIGHT: (C)2009,JPO&INPIT

Description

  The present invention relates to an amide compound and its use for controlling plant diseases.

が知られている（例えば、非特許文献１参照。）。 Conventionally, many compounds have been developed and put into practical use as active ingredients of plant disease control agents. However, these compounds may not always show sufficient control efficacy.
N- (2-chlorobenzyl) -6-quinolinecarboxylic acid amide (a compound represented by the following formula (A))

Is known (see, for example, Non-Patent Document 1).

Acta Poloniae Pharmaceutica (1966), 23, p.9-17

  An object of the present invention is to provide a compound having an excellent control effect against plant diseases.

で示されるアミド化合物（以下、本発明化合物と記す。）、本発明化合物を有効成分として含有する植物病害防除剤、及び、本発明化合物の有効量を植物又は土壌に処理する工程を有してなる植物病害の防除方法を提供する。 As a result of studies to find a compound having an excellent control effect against plant diseases, the present inventors have found that the amide compound represented by the following formula (I) has an excellent control effect against plant diseases. The headline, the present invention has been reached.
That is, the present invention relates to the formula (I)

A plant disease control agent containing the compound of the present invention as an active ingredient, and a step of treating the plant or soil with an effective amount of the compound of the present invention. A method for controlling plant diseases is provided.

  Since the compound of the present invention has an excellent control effect against plant diseases, it is useful as an active ingredient of a plant disease control agent.

The manufacturing method of this invention compound is demonstrated.
The compound of the present invention can be produced, for example, by the following (Production Method 1) or (Production Method 2).

該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばテトラヒドロフラン（以下、ＴＨＦと記す場合がある。）、エチレングリコールジメチルエーテル、ｔｅｒｔ−ブチルメチルエーテル（以下、ＭＴＢＥと記す場合がある。）等のエーテル類、ヘキサン、へプタン、オクタン等の脂肪族炭化水素類、トルエン、キシレン等の芳香族炭化水素類、クロロベンゼン等のハロゲン化炭化水素類、酢酸ブチル、酢酸エチル等のエステル類、アセトニトリル等のニトリル類、Ｎ，Ｎ−ジメチルホルムアミド（以下、ＤＭＦと記す場合がある。）等の酸アミド類、ジメチルスルホキシド（以下、ＤＭＳＯと記す場合がある。）等のスルホキシド類、ピリジン等の含窒素芳香族化合物類等及びこれらの混合物が挙げられる。
反応に用いられる脱水縮合剤としては、１−エチル−３−（３−ジメチルアミノプロピル）カルボジイミド塩酸塩（以下、ＷＳＣと記す。）、（ベンゾトリアゾール−１−イルオキシ）トリス（ジメチルアミノ）ホスホニウムヘキサフルオロホスフェート（以下、ＢＯＰ試薬と記す場合がある。）及び１，３−ジシクロヘキシルカルボジイミド等のカルボジイミド類が挙げられる。必要に応じて、化合物（II）１モルに対して通常１〜１０モルの割合のトリエチルアミンなどの有機塩基を合わせて用いることができる。
化合物（II）１モルに対して、化合物（III）が通常０．５〜３モルの割合、脱水縮合剤が通常１〜５モルの割合で用いられる。
該反応の反応温度は、通常−２０℃〜１４０℃の範囲であり、反応時間は通常１〜２４時間の範囲である。
反応終了後は、水を加えた後、固体が析出した場合は、濾過することにより本発明化合物を単離することができ、また、固体が析出しない場合は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、本発明化合物を単離することができる。単離された本発明化合物は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Production method 1)
The compound of the present invention is produced by reacting compound (II) with compound (III) or a salt thereof (for example, hydrochloride and hydrobromide) in the presence of a dehydration condensing agent. Can do.

The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as tetrahydrofuran (hereinafter sometimes referred to as THF), ethylene glycol dimethyl ether, tert-butyl methyl ether (hereinafter sometimes referred to as MTBE), hexane, and the like. Aliphatic hydrocarbons such as pentane and octane, aromatic hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as chlorobenzene, esters such as butyl acetate and ethyl acetate, nitriles such as acetonitrile, N, N -Acid amides such as dimethylformamide (hereinafter sometimes referred to as DMF), sulfoxides such as dimethyl sulfoxide (hereinafter sometimes referred to as DMSO), nitrogen-containing aromatic compounds such as pyridine, and the like Of the mixture.
Examples of the dehydrating condensing agent used in the reaction include 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (hereinafter referred to as WSC), (benzotriazol-1-yloxy) tris (dimethylamino) phosphonium hexa Examples thereof include carbodiimides such as fluorophosphate (hereinafter sometimes referred to as BOP reagent) and 1,3-dicyclohexylcarbodiimide. If necessary, an organic base such as triethylamine in a proportion of usually 1 to 10 moles relative to 1 mole of compound (II) can be used.
The compound (III) is usually used in a proportion of 0.5 to 3 mol and the dehydrating condensing agent is usually used in a proportion of 1 to 5 mol with respect to 1 mol of the compound (II).
The reaction temperature of the reaction is usually in the range of −20 ° C. to 140 ° C., and the reaction time is usually in the range of 1 to 24 hours.
After completion of the reaction, if a solid precipitates after adding water, the compound of the present invention can be isolated by filtration. If the solid does not precipitate, the reaction mixture is extracted with an organic solvent. The compound of the present invention can be isolated by post-treatment operations such as drying and concentration of the organic layer. The isolated compound of the present invention can be further purified by chromatography, recrystallization and the like.

該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばＴＨＦ、エチレングリコールジメチルエーテル、ＭＴＢＥ等のエーテル類、ヘキサン、へプタン、オクタン等の脂肪族炭化水素類、トルエン、キシレン等の芳香族炭化水素類、クロロベンゼン等のハロゲン化炭化水素類、酢酸ブチル、酢酸エチル等のエステル類、アセトニトリル等のニトリル類及びこれらの混合物が挙げられる。
反応に用いられる塩基としては、炭酸ナトリウム、炭酸カリウム等のアルカリ金属炭酸塩類、トリエチルアミン、ジイソプロピルエチルアミン等の第３級アミン類及びピリジン、４−ジメチルアミノピリジン等の含窒素芳香族化合物類等が挙げられる。
化合物（IV）１モルに対して、化合物（III）が通常０．５〜３モルの割合、塩基が通常１〜５モルの割合で用いられる。
該反応の反応温度は通常−２０〜１００℃の範囲であり、反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、水を加えた後、固体が析出した場合は、濾過することにより本発明化合物を単離することができ、また、固体が析出しない場合は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、本発明化合物を単離することができる。単離された本発明化合物は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Production method 2)
The compound of the present invention can be produced by reacting compound (IV) with compound (III) or a salt thereof (for example, hydrochloride and hydrobromide) in the presence of a base. .

The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, and MTBE, aliphatic hydrocarbons such as hexane, heptane, and octane, aromatic hydrocarbons such as toluene and xylene, and halogens such as chlorobenzene. Hydrocarbons, esters such as butyl acetate and ethyl acetate, nitriles such as acetonitrile, and mixtures thereof.
Examples of the base used in the reaction include alkali metal carbonates such as sodium carbonate and potassium carbonate, tertiary amines such as triethylamine and diisopropylethylamine, and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine. It is done.
The compound (III) is usually used in a proportion of 0.5 to 3 mol and the base is usually used in a proportion of 1 to 5 mol with respect to 1 mol of the compound (IV).
The reaction temperature of the reaction is usually in the range of -20 to 100 ° C, and the reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, if a solid precipitates after adding water, the compound of the present invention can be isolated by filtration. If the solid does not precipitate, the reaction mixture is extracted with an organic solvent. The compound of the present invention can be isolated by post-treatment operations such as drying and concentration of the organic layer. The isolated compound of the present invention can be further purified by chromatography, recrystallization and the like.

  The control agent of the present invention may be composed only of the compound of the present invention. Usually, the compound of the present invention is mixed with a solid carrier, a liquid carrier, a gas carrier, a surfactant, etc. Additives for formulation such as powders and stabilizers, wettable powder, wettable powder, flowable powder, granules, dry flowable powder, emulsion, aqueous liquid, oil, smoke, aerosol, microcapsule It is used in the form of a preparation. In these preparations, the compound of the present invention is usually contained in an amount of 0.1 to 99%, preferably 0.2 to 90% by weight.

  Examples of the solid carrier include clays (for example, kaolin, diatomaceous earth, synthetic hydrous silicon oxide, fusami clay, bentonite, acidic clay), talc, and other inorganic minerals (for example, sericite, quartz powder, sulfur powder, activated carbon, Examples of the liquid carrier include water, alcohols (for example, methanol, ethanol), ketones (for example, acetone, methyl ethyl ketone), aromatic carbonization, and the like. Hydrogens (eg, benzene, toluene, xylene, ethylbenzene, methylnaphthalene), aliphatic hydrocarbons (eg, n-hexane, cyclohexanone, kerosene), esters (eg, ethyl acetate, butyl acetate), nitriles (eg, , Acetonitrile, isobutylnitrile), ethers (eg , Dioxane, diisopropyl ether), acid amides (e.g., dimethylformamide, dimethylacetamide), halogenated hydrocarbons (e.g., dichloroethane, trichlorethylene, and carbon tetrachloride), and the like.

  Surfactants include, for example, alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and their polyoxyethylene compounds, polyoxyethylene glycol ethers, polyhydric alcohol esters, sugar alcohol derivatives. Etc.

  Other formulation adjuvants include, for example, fixing agents and dispersants, specifically casein, gelatin, polysaccharides (eg starch, arabic gum, cellulose derivatives, alginic acid), lignin derivatives, bentonite, saccharides, synthetic water-soluble high Molecules (for example, polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acids), PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (2-tert-butyl-4) -Mixtures of methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oils, mineral oils, fatty acids or esters thereof.

  The method of applying the present control agent is not particularly limited as long as the method of the present invention can be applied substantially, but for example, treatment to plant bodies such as foliage spraying, plant such as soil treatment, etc. And the like, and the treatment of seeds such as seed disinfection.

In addition, the present control agent may be used simultaneously with or without mixing with other fungicides, insecticides, acaricides, nematicides, herbicides, plant growth regulators, fertilizers or soil conditioners. You can also.
Such other fungicides include, for example, propiconazole, prothioconazole, triazimenol, prochloraz, penconazole, tebuconazole, flusilazole, diniconazole, bromconazole, epoxiconazole, difenoconazole, cyproconazole, metconazole, triflumi Azole fungicides such as sol, tetraconazole, microbutanyl, fenbuconazole, hexaconazole, fluquinconazole, triticonazole, vitertanol, imazalyl, flutriahol; fenpropimorph, tridemorph, fenpropidin, etc. Cyclic amine bactericidal compounds: benzimidazole bactericidal compounds such as carbendazim, benomyl, thiabendazole, thiophanate methyl; procymidone; ciprodini Pyrimethanyl; Dietofencarb; Thiuram; Fluazinam; Mancozeb; Iprodione; Vinclozoline; Chlorotalonyl; Captan; Mepanipyrim; Fenpiclonyl; Fludioxonil; Xylostrobin; pyraclostrobin; dimoxystrobin; pyribencarb; spiroxamine; quinoxyphene; fenhexamide; famoxadone; fenamidone; zoxamide; ethaboxam; Metolaphenone; fluopyran; bixafen; cyflufenamide and Kinajido and the like.

  The application amount of the present control agent varies depending on weather conditions, formulation form, application time, application method, application location, target disease, target crop, etc., but per 10 ares in terms of the amount of the present compound in the present control agent, Usually 1 to 500 g, preferably 2 to 200 g. Emulsions, wettable powders, suspensions and the like are usually diluted with water and applied. In this case, the concentration of the compound of the present invention after dilution is usually 0.0005 to 2% by weight, preferably 0.005 to 1. The powder, granules and the like are usually applied as they are without dilution. In the seed treatment, the amount of the compound of the present invention in the control agent of the present invention is generally 0.001 to 100 g, preferably 0.01 to 50 g per 1 kg of seed.

  The control agent of the present invention can be used as a plant disease control agent in agricultural land such as fields, paddy fields, lawns, orchards. The control agent of the present invention can control diseases of the farmland in the farmland where the following “crop” and the like are cultivated.

Agricultural crops: corn, rice, wheat, barley, rye, oats, sorghum, cotton, soybeans, peanuts, buckwheat, sugar beet, rapeseed, sunflower, sugarcane, tobacco, vegetables, solanaceous vegetables (eggplant, tomato, pepper, pepper, potato) Cucumber, pumpkin, zucchini, watermelon, melon, etc., cruciferous vegetables (radish, turnip, horseradish, kohlrabi, cabbage, cabbage, mustard, broccoli, cauliflower, etc.), asteraceae (burdock, Shungiku, artichokes, lettuce, etc.), liliaceae vegetables (leek, onion, garlic, asparagus), celeryaceae vegetables (carrot, parsley, celery, red pepper, etc.), red crustacean vegetables (spinach, chard, etc.) (Perilla, mint, basil ), Strawberry, sweet potato, yam, taro, etc.,
Bridegroom,
Foliage plant,
Fruit trees; pears (apples, pears, Japanese pears, quince, quince, etc.), nuclear fruits (peaches, plums, nectarines, ume, sweet cherry, apricots, prunes, etc.), citrus (satsuma mandarin, orange, lemon, lime, grapefruit) ), Nuts (chestnut, walnut, hazel, almond, pistachio, cashew nut, macadamia nut, etc.), berries (blueberry, cranberry, blackberry, raspberry, etc.), grape, oyster, olive, loquat, banana, coffee, Date palm, coconut palm, etc.
Trees other than fruit trees: Cha, mulberry, flowering trees, street trees (ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, oak, poplar, redwood, fu, sycamore, zelkova, black bean, peach tree, Tsuga, rat, pine, Spruce, yew) etc.

  The above `` crop '' is resistant to HPPD inhibitors such as isoxaflutol, ALS inhibitors such as imazetapyr and thifensulfuron methyl, EPSP synthase inhibitors, glutamine synthase inhibitors, herbicides such as bromoxynil, This includes crops granted by classical breeding methods or genetic engineering techniques.

  As an example of a “crop” to which resistance has been imparted by a classic breeding method, imidazolinone herbicide-resistant Clearfield (registered trademark) canola, such as imazetapil, and sulfonylurea-based ALS-inhibiting herbicide resistance such as thifensulfuron methyl There are STS soybeans. In addition, examples of “crop” that have been given resistance by genetic engineering include maize varieties resistant to glyphosate and glufosinate, which are already sold under trade names such as RoundupReady (registered trademark) and LibertyLink (registered trademark). Has been.

The “crop” includes, for example, a crop that can synthesize selective toxins known in the genus Bacillus by using genetic recombination technology.
Toxins expressed in such genetically modified plants include insecticidal proteins from Bacillus cereus and Bacillus popirie; Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C from Bacillus thuringiensis Insecticidal protein such as δ-endotoxin, VIP1, VIP2, VIP3 or VIP3A; nematode-derived insecticidal protein; toxin produced by animals such as scorpion toxin, spider toxin, bee toxin or insect-specific neurotoxin; filamentous fungal toxin; plant Lectin; agglutinin; protease inhibitor such as trypsin inhibitor, serine protease inhibitor, patatin, cystatin, papain inhibitor; ribosome inactivating protein (RIP) such as lysine, corn-RIP, abrin, ruffin, saporin, bryodin; 3-hydroxysteroid oxidase, ecdysteroid Steroid metabolic enzymes such as UDP-glucosyltransferase and cholesterol oxidase; ecdysone inhibitor; HMG-COA reductase; ion channel inhibitor such as sodium channel and calcium channel inhibitor; juvenile hormone esterase; diuretic hormone receptor; stilbene synthase; Benzyl synthase; chitinase; glucanase and the like.

In addition, as toxins expressed in such genetically modified crops, Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, δ-endotoxin proteins such as Cry3Bb1 or Cry9C, and insecticidal protein hybrids such as VIP1, VIP2, VIP3 or VIP3A Toxins, partially defective toxins, modified toxins are also included. Hybrid toxins are produced by new combinations of different domains of these proteins using recombinant techniques. As a toxin lacking a part, Cry1Ab lacking a part of the amino acid sequence is known. In the modified toxin, one or more amino acids of the natural toxin are substituted.
Examples of these toxins and recombinant plants capable of synthesizing these toxins are EP-A-0 374 753, WO 93/07278, WO 95/34656, EP-A-0 427 529, EP-A-451 878. , WO 03/052073 and the like.
The toxins contained in these recombinant plants particularly confer resistance to Coleoptera pests, Diptera pests, and Lepidoptera pests.

  Also, genetically modified plants that contain one or more insecticidal pest resistance genes and express one or more toxins are already known, and some are commercially available. Examples of these transgenic plants include YieldGard® (a corn variety expressing Cry1Ab toxin), YieldGard Rootworm® (a corn variety expressing Cry3Bb1 toxin), YieldGard Plus® (Cry1Ab and Cry3Bb1 Corn varieties expressing toxins), Herculex I® (corn varieties expressing phosphinotricin N-astilyltransferase (PAT) to confer resistance to Cry1Fa2 toxin and glufosinate), NuCOTN33B (Cry1Ac toxin) Cotton varieties expressing), Bollgard I (registered trademark) (cotton varieties expressing Cry1Ac toxin), Bollgard II (registered trademark) (cotton varieties expressing Cry1Ac and Cry2Ab toxin), VIPCOT (registered trademark) (VIP toxin) Cotton varieties), NewLeaf (registered trademark) (potato varieties expressing Cry3A toxin), NatureGard (registered trademark) Agrisure (registered trademark) GT Advant Examples include age (GA21 glyphosate resistance trait), Agrisure (registered trademark) CB Advantage (Bt11 corn borer (CB) trait), Protecta (registered trademark), and the like.

The above “crop” includes those given the ability to produce an anti-pathogenic substance having a selective action using genetic recombination technology.
PR proteins and the like are known as examples of anti-pathogenic substances (PRPs, EP-A-0 392 225). Such anti-pathogenic substances and genetically modified plants that produce them are described in EP-A-0 392 225, WO 95/33818, EP-A-0 353 191 and the like.
Examples of anti-pathogenic substances expressed in such genetically modified plants include, for example, sodium channel inhibitors and calcium channel inhibitors (KP1, KP4, KP6 toxins produced by viruses, etc.) are known. Ion channel inhibitors; stilbene synthase; bibenzyl synthase; chitinase; glucanase; PR protein; peptide antibiotics, heterocyclic antibiotics, protein factors involved in plant disease resistance (called plant disease resistance genes, WO 03/000906)) and other anti-pathogenic substances produced by microorganisms.

Examples of plant diseases that can be controlled by the present invention include filamentous fungi and the like, and more specifically, the following diseases can be mentioned, but are not limited thereto.
Usually, this invention control method is performed by using this invention control agent by the method of applying this invention control agent mentioned above.

Rice blast (Magnaporthe grisea), sesame leaf blight (Cochliobolus miyabeanus), blight (Rhizoctonia solani), idiot seedling (Gibberella fujikuroi);
Wheat powdery mildew (Erysiphe graminis), red mold (Fusarium graminearum, F. avenacerum, F. culmorum, Microdochium nivale), rust (Puccinia striiformis, P. graminis, P. recondita, P. hordei), snow Rot (Typhula sp., Micronectriella nivalis), Bare Scarf (Ustilago tritici, U. nuda), Namahusa scab (Tilletia caries), Eye ailment (Pseudocercosporella herpotrichoides), Cloud disease (Rhynchosporium secalis), Leaf blight ( Septoria tritici), blight (Leptosphaeria nodorum), net blotch (Pyrenophora teres Drechsler), blight (Gaeumannomyces graminis);
Citrus spot disease (Diaporthe citri), scab (Elsinoe fawcetti), fruit rot (Penicillium digitatum, P. italicum);
Monilinia mali, apple rot (Valsa ceratosperma), powdery mildew (Podosphaera leucotricha), spotted leaf (Alternaria alternata apple pathotype), black rot (Venturia inaequalis), anthracnose (Glomerella cingulata);
Pear black spot disease (Venturia nashicola, V. pirina), black spot disease (Alternaria alternata Japanese pear pathotype), red star disease (Gymnosporangium haraeanum);
Peach ash scab (Monilinia fructicola), black scab (Cladosporium carpophilum), Phomopsis sp. (Phomopsis sp.);

Grapes black rot (Elsinoe ampelina), late rot (Glomerella cingulata), powdery mildew (Uncinula necator), rust (Phakopsora ampelopsidis), black lot disease (Guignardia bidwellii), downy mildew (Plasmopara viticola);
Oyster anthracnose (Gloeosporium kaki), deciduous leaf disease (Cercospora kaki, Mycosphaerella nawae);
Colletotrichum lagenarium, powdery mildew (Sphaerotheca fuliginea), vine blight (Mycosphaerella melonis), vine split (Fusarium oxysporum), downy mildew (Pseudoperonospora cubensis), plague (Phytophthora sp.) Seedling blight (Pythium sp.);
Tomato ring disease (Alternaria solani), leaf mold (Cladosporium fulvum), plague (Phytophthora infestans);
Eggplant brown spot (Phomopsis vexans), powdery mildew (Erysiphe cichoracearum);
Brassicaceae vegetable black spot (Alternaria japonica), white spot (Cercosporella brassicae);
Leek rust (Puccinia allii), soybean purpura (Cercospora kikuchii), black scab (Elsinoe glycines), black spot (Diaporthe phaseolorum var. Sojae), rust (Phakopsora pachyrhizi)
Green Bean Anthracnose (Colletotrichum lindemthianum)
Groundnut black astringency (Cercospora personata), brown spot (Cercospora arachidicola), white silkworm (Sclerotium rolfsii);
Pea powdery mildew (Erysiphe pisi);
Potato summer plague (Alternaria solani), plague (Phytophthora infestans), half body wilt (Verticillium albo-atrum, V. dahliae, V. nigrescens);
Strawberry powdery mildew (Sphaerotheca humuli);
Tea net blast (Exobasidium reticulatum); white spot (Elsinoe leucospila), ring spot (Pestalotiopsis sp.), Anthracnose (Colletotrichum theae-sinensis)
Tobacco red blight (Alternaria longipes), powdery mildew (Erysiphe cichoracearum), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina), plague (Phytophthora nicotianae);

Sugar beet brown spot (Cercospora beticola), leaf rot (Thanatephorus cucumeris), root rot (Thanatephorus cucumeris);
Rose scab (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa);
Chrysanthemum brown spot (Septoria chrysanthemi-indici), white rust (Puccinia horiana);
Onion leaf blight (Botrytis cinerea, B. byssoidea, B. squamosa), gray rot (Botrytis alli), sclerotia rot (Botrytis squamosa);
Various crops of gray mold (Botrytis cinerea), mycorrhizal disease (Sclerotinia sclerotiorum); radish black soot (Alternaria brassicicola);
Shiva dollar spot disease (Sclerotinia homeocarpa), Shiva brown patch disease and Rhizoctonia solani; and banana Sigatoka disease (Mycosphaerella fijiensis, Mycosphaerella musicola, Pseudocercospora musae).

Hereinafter, although this invention is demonstrated in more detail by a manufacture example, a formulation example, a test example, etc., this invention is not limited only to these examples.
First, the manufacture example of this invention compound is shown.

¹H-NMR (CDCl₃) δ: 4.76 (2H, d, J = 5.9 Hz), 6.73 (1H, br), 7.07-7.17 (2H), 7.27-7.33 (1H, m), 7.45-7.49 (2H), 8.05 (1H, dd, J = 8.8 Hz, 2.2 Hz), 8.15 (1H, d, J = 8.8 Hz), 8.22 (1H, dd, J = 8.5 Hz, 1.0 Hz), 8.31 (1H, d, J = 2.0 Hz), 9.08 (1H, dd, J = 4.4 Hz, 1.7 Hz)． Production Example 6 To a mixture of 5.20 g of 6-quinolinecarboxylic acid, 4.13 g of 2-fluorobenzylamine and 40 ml of DMF, 14.6 g of BOP reagent and 6.68 g of triethylamine were sequentially added and stirred at room temperature for 4 hours. Ice and water were added to the reaction mixture, and the mixture was stirred at room temperature for 1 hour and then under ice cooling for 1 hour. The resulting solid was collected by filtration and washed successively with water and tert-butyl methyl ether to obtain 9.04 g of a solid. This was recrystallized from methanol to obtain 6.51 g of the present compound.
Compound of the present invention

¹ H-NMR (CDCl ₃ ) δ: 4.76 (2H, d, J = 5.9 Hz), 6.73 (1H, br), 7.07-7.17 (2H), 7.27-7.33 (1H, m), 7.45-7.49 (2H ), 8.05 (1H, dd, J = 8.8 Hz, 2.2 Hz), 8.15 (1H, d, J = 8.8 Hz), 8.22 (1H, dd, J = 8.5 Hz, 1.0 Hz), 8.31 (1H, d, J = 2.0 Hz), 9.08 (1H, dd, J = 4.4 Hz, 1.7 Hz).

  Next, formulation examples are shown. In addition, a part represents a weight part.

Formulation Example 1
The wettable powder is obtained by thoroughly pulverizing and mixing 50 parts of the compound of the present invention, 3 parts of calcium lignin sulfonate, 2 parts of magnesium lauryl sulfate and 45 parts of synthetic silicon hydroxide.

Formulation Example 2
20 parts of the compound of the present invention and 1.5 parts of sorbitan trioleate are mixed with 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol, finely pulverized by a wet pulverization method, and then xanthan gum 0 0.05 part and 40 parts of an aqueous solution containing 0.1 part of aluminum magnesium silicate are added, and further 10 parts of propylene glycol is added and mixed by stirring to obtain a flowable preparation.

Formulation Example 3
By thoroughly pulverizing and mixing 2 parts of the compound of the present invention, 88 parts of kaolin clay and 10 parts of talc, a powder is obtained.

Formulation Example 4
An emulsion is obtained by thoroughly mixing 5 parts of the compound of the present invention, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 75 parts of xylene.

Formulation Example 5
By thoroughly pulverizing and mixing 2 parts of the present compound, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay, kneaded well with water, granulated and dried, Get a granule.

Formulation Example 6
A flowable preparation is obtained by mixing 35 parts of white carbon containing 10 parts of the compound of the present invention, 50 parts of polyoxyethylene alkyl ether sulfate ammonium salt and 55 parts of water and finely pulverizing them by a wet pulverization method.

Next, test examples show that the compounds of the present invention are useful for controlling plant diseases.
The control effect is obtained by visually observing the area of the lesion on the test plant at the time of the survey, and comparing the area of the lesion on the plant treated with the compound of the present invention and the area of the lesion on the untreated plant. evaluated.

をあわせて試験に供試した。 As a control, N- (2-chlorobenzyl) -quinoline-6-carboxylic acid amide (a compound represented by the following formula (A) described in Acta Poloniae Pharmaceutica (1966), 23, p.9-17. (Referred to as comparative compound (A))

Were used in the test.

Test example 1
Cucumber gray mold prevention effect test (Botrytis cinerea)
A plastic pot was filled with sandy loam, cucumber (variety: Sagamihanjiro) was sown and grown in a greenhouse for 12 days. Each of the compound of the present invention and the comparative compound (A) was made into a flowable formulation according to Formulation Example 6, diluted with water to a predetermined concentration (200 ppm), and sprayed on the foliage so as to adhere well to the cucumber leaf surface. After spraying, the plants were air-dried, and a PDA medium containing spores of cucumber gray mold was placed on the cucumber leaf surface. After inoculation, the lesion area was investigated after 5 days in a humid environment at 12 ° C. As a result, the lesion area in the plant treated with the compound of the present invention was 0%. The lesion area on the plant on which the comparative compound (A) was tested was 98% of the lesion area in the untreated group.

Test example 2
Treatment effect test of cucumber gray mold (Botrytis cinerea)
A plastic pot was filled with sand loam, sown with cucumber (Sagamihanjiro), and grown in a greenhouse for 12 days. Thereafter, a PDA medium containing spores of cucumber gray mold fungus is inoculated on the cucumber leaf surface, each of the compound of the present invention and the comparative compound (A) is flowable formulated according to Formulation Example 6, and then diluted with water to a predetermined concentration. (200 ppm), and the spray solution was sprayed on the foliage so that it sufficiently adhered to the leaf surface of the cucumber. After spraying, the plants were air-dried and placed under high humidity at 12 ° C. for 2 days, and then the control effect was investigated. As a result, the lesion area of the plant treated with the compound of the present invention was 12% of the lesion area in the untreated section. On the other hand, the lesion area on the plant treated with the comparative compound (A) was 98% of the lesion area in the untreated section.

Test example 3
Cucumber nuclear disease prevention effect test (Sclerotinia sclerotiorum)
A plastic pot was filled with sandy loam, cucumber (variety: Sagamihanjiro) was sown and grown in a greenhouse for 12 days. The compound of the present invention was made into a flowable formulation according to Formulation Example 6, diluted with water to a predetermined concentration (200 ppm), and sprayed on the foliage so as to adhere well to the cucumber leaf surface. After spraying, the plants were air-dried, and a mycelia-containing PDA medium containing mycorrhizal fungi was placed on the cucumber leaf surface. After the inoculation, the lesion area was examined after being placed at 18 ° C. under high humidity for 4 days. As a result, the lesion area in the plant treated with the compound of the present invention was 0%.

Claims (4)

Formula (I)

An amide compound represented by   A plant disease control agent comprising the amide compound according to claim 1 as an active ingredient.   A method for controlling plant diseases comprising a step of treating an effective amount of the amide compound according to claim 1 to a plant or soil.   Use of the amide compound according to claim 1 for controlling plant diseases by treating the plant or soil.