Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
  • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
  • C07D277/62—Benzothiazoles
  • C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
  • C07D277/82—Nitrogen atoms

Definitions

• the present invention relates to an amide compound and a plant disease controlling use thereof.
• the present invention provides a compound having an excellent controlling effect on plant diseases.
• the present inventions are as follows.
• R represents a hydrogen atom or a fluorine atom and R represents a
• a plant disease controlling composition comprising the amide compound according to any one of [1] to [30] and an inert carrier.
• a plant disease controlling method having a step of applying a plant or soil with an effective amount of the amide compound according to any one of [1] to [30].
• the compound of the present invention includes, for example, the following embodiments.
• the compound of the present invention can be produced, for example, by the following (Production Method 1) to (Production Method 3). (Production Method 1)
• the compound of the present invention can be produced by reacting a compound (III) and a compound (II) or its salt (for example, hydrochloride and hydrobromide are listed) in the presence of a condensing agent.
• R 1 and R 2 have the same meaning as defined above.
• the reaction is carried out usually in the presence of a solvent.
• ethers such as tetrahydrofuran (hereinafter, referred to as THF), ethylene glycol dimethyl ether and tert-butyl methyl ether (hereinafter, referred to as MTBE); aliphatic hydrocarbons such as hexane, heptane 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; acid amides such as N,N-dimethylformamide (hereinafter, referred to as DMF); sulfoxides such as dimethyl sulfoxide (hereinafter, referred to as DMSO); nitrogen-containing aromatic compounds such as pyridine; and mixtures thereof.
• THF tetrahydrofuran
• MTBE tert-butyl methyl ether
• Examples of the condensing agent used in the reaction include carbodiimides such as l-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (hereinafter, referred to as WSC) and 1,3-dicyclohexyl- carbodiimide, and (benzotriazol- l-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (hereinafter, referred to as BOP reagent).
• WSC l-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride
• BOP reagent 1,3-dicyclohexyl- carbodiimide
• the compound (III) is used usually in a proportion of 0.5 to 3 mol based on 1 mol of the compound (II), and the condensing agent is used usually in a proportion of 1 to 5 mol based on 1 mol of the compound (II).
• the reaction temperature of the reaction is usually in the range of from -20 0 C to 140 0 C.
• the reaction time of the reaction is usually in the range of from 1 to 24 hours.
• the compound of the present invention can be isolated by filtration. If no deposition of a solid occurs by adding water to the reaction mixture, the compound of the present invention can be isolated by extracting a mixture of the reaction mixture and water with an organic solvent and drying and concentrating the organic layer. The isolated compound of the present invention can also be further purified by chromatography, re-crystallization and so on.
• the compound of the present invention can be produced by reacting a compound (V) or its hydrochloride, and a compound (III) or its salt (for example, hydrochloride and hydrobromide are mentioned) in the presence of a base.
• R 1 and R 2 have the same meaning as defined above.
• the reaction is carried out usually in the presence of a solvent.
• solvent used in the reaction examples 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; halogenated hydrocarbons such as chlorobenzene; esters such as butyl acetate and ethyl acetate; nitriles such as acetonitrile; and mixtures thereof.
• 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
• halogenated hydrocarbons such as chlorobenzene
• esters such as butyl acetate and ethyl acetate
• nitriles such as acetonitrile
• 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.
• alkali metal carbonates such as sodium carbonate and potassium carbonate
• tertiary amines such as triethylamine and diisopropylethylamine
• nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine.
• the compound (II) is used usually in a proportion of 0.5 to 3 mol based on 1 mol of the compound (IV), and the base is used usually in a proportion of 1 to 5 mol based on 1 mol of the compound (IV).
• the reaction temperature of the reaction is usually in the range of from
• reaction time of the reaction is usually in the range of from 0.1 to 24 hours.
• the compound of the present invention can be isolated by filtration. If no deposition of a solid occurs by adding water to the reaction mixture, the compound of the present invention can be isolated by extracting a mixture of the reaction mixture and water with an organic solvent and drying and concentrating the organic layer. The isolated compound of the present invention can also be further purified by chromatography, re-crystallization and so on.
• the compound of the present invention can be produced by reacting an amide compound (II) and a compound (VI) in the presence of a base.
• solvent used in the reaction examples include ethers such as THF, ethylene glycol dimethyl ether and MTBE; aromatic hydrocarbons such as toluene and xylene; halogenated hydrocarbons such as chlorobenzene; nitriles such as acetonitrile; acid amides such as DMF; sulfoxides such as DMSO; ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone; water; and mixtures thereof.
• ethers such as THF, ethylene glycol dimethyl ether and MTBE
• aromatic hydrocarbons such as toluene and xylene
• halogenated hydrocarbons such as chlorobenzene
• nitriles such as acetonitrile
• acid amides such as DMF
• sulfoxides such as DMSO
• ketones such as acetone, methyl ethyl ketone and methyl isobutyl ket
• Examples of the base used in the reaction include alkali metal carbonates such as sodium carbonate, potassium carbonate and cesium carbonate; alkali metal hydroxides such as sodium hydroxide, and alkali metal hydrides such as sodium hydride.
• the compound (VI) is used usually in a proportion of 1 to 10 mol based on 1 mol of the compound (V) 5 and the base is used usually in a proportion of 1 to 5 mol based on 1 mol of the compound (V).
• the reaction temperature of the reaction is usually in the range of from
• reaction time of the reaction is usually in the range of from 0.1 to 24 hours.
• the compound of the present invention can be isolated by filtration. If no deposition of a solid occurs by adding water to the reaction mixture, the compound of the present invention can be isolated by extracting a mixture of the reaction mixture and water with an organic solvent and drying and concentrating the organic layer. The isolated compound of the present invention can also be further purified by chromatography, re-crystallization and so on.
• the compound (V) can be produced, for example, by the following (Synthesis Method ). (Synthesis Method )
• the compound (V) can be produced by de-protecting a protective group of the compound (VII).
• Z represents a protective group such as a tert-butyldimethylsilyl group, methyl group, methoxymethyl group, benzyl group and acetyl group.
• solvent used in the reaction examples include ethers such as THF, ethylene glycol dimethyl ether and MTBE, aromatic hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as chlorobenzene, nitriles such as acetonitrile, acid amides such as DMF, sulfoxides such as dimethyl sulfoxide, ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone, water, and mixtures thereof.
• ethers such as THF, ethylene glycol dimethyl ether and MTBE
• aromatic hydrocarbons such as toluene and xylene
• halogenated hydrocarbons such as chlorobenzene
• nitriles such as acetonitrile
• acid amides such as DMF
• sulfoxides such as dimethyl sulfoxide
• ketones such as acetone, methyl ethyl ketone and
• the base and fluoride used in the de-protecting reaction include alkali metal hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide, and fluorine compounds such as sodium fluoride, tetrabutylammonium hydrofluoride and hydrofluoric acid.
• the base and fluorine compound are used usually in a proportion of 1 to 10 mol with respect to 1 mol of the compound (VII).
• the reaction temperature of this reaction is usually in the range of from -20 to 100°C and the reaction time is usually in the range of from 0.1 to 24 hours.
• the compound (V) can be isolated.
• the isolated compound (V) can also be further purified by chromatography and recrystallization.
• the compound of the present invention include, specifically, N-benzothiazol-6-yl-2-(2-fluoro-3-(2-propenyloxy)phenyl)acetamide, N-benzothiazol-6-yl-2-(2-fluoro-3-(2-butenyloxy)phenyl)acetamide, N-benzothiazol-6-yl-2-(2-fluoro-3-(3-butenyloxy)phenyl)acetamide, N-benzothiazol-6-yl-2-(2-fluoro-3-(2- ⁇ entenyloxy)phenyl)acetamide, N-benzothiazol-6-yl-2-(2-fluoro-3-(3- ⁇ entenyloxy)phenyl)acetamide, N-benzothiazol-6-yl-2-(2-fluoro-3-(4- ⁇ entenyloxy)phenyl)acetamide, N-benzothiazol-6-yl-2-(2-fluoro-3-(2-
• the plant disease controlling composition of the present invention contains a compound of the present invention and an inert carrier.
• the inert carrier includes solid carriers, liquid carriers and gas carriers.
• the plant disease controlling composition of the present invention is usually formulated into a wettable powder, dust, water dispersible granule, flowable, granule, dry flowable, emulsiflable concentrate, aqueous liquid agent, oil solution, smoking agent, aerosol, microcapsules and so on by further addition of auxiliary agents for formulation such as a surfactant, a sticking agent, a dispersing agent and a stabilizing agent.
• the plant disease controlling composition of the present invention contains the compound of the present invention in a weight ratio of usually 0.1 to 99%, preferably 0.2 to 90%.
• the solid carrier examples include fine powders and granules of clays (for example, kaolin, diatomaceous earth, synthetic hydrated silicon oxide, Fubasami clay, bentonite and acid clay), talc, other inorganic minerals (for example, sericite, quart powder, sulfur power, activated carbon, calcium carbonate and hydrated silica) and so on, and examples of the liquid carrier include water; alcohols (for example, methanol and ethanol), ketones (for example, acetone and methyl ethyl ketone), aromatic hydrocarbons (for example, benzene, toluene, xylene, ethylbenzene and methylnaphthalene), aliphatic hydrocarbons (for example, n-hexane, cyclohexane and kerosene), esters (for example, ethyl acetate and butyl acetate), nitriles (for example, acetonitrile and isobutyronitrile
• surfactant examples include alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and their polyoxyethylenate, polyoxyethylene glycol ethers, poly-valent alcohol esters, sugar alcohol derivatives, and so on.
• auxiliary agents for formulation examples include sticking agents and dispersing agents, specifically, casein, gelatin, polysaccharides (for example, starch, gum Arabic, cellulose derivatives and alginic acid), lignin derivatives, bentonite, sugars, synthetic water-soluble polymers (for example, polyvinyl alcohol, polyvinylpyrrolidone and polyacrylic acids), PAP (acidic isopropyl phosphate), BHT (2,6-di-tert-butyl-4-methyl-phenol), BHA (a mixture of
• the use method of the plant disease controlling composition of the present invention for controlling a plant disease includes, for example, treatment on plants such as spraying on stem and leaves, treatment on cultivation ground for plant such as soil treatment, and treatment on seed such as seed disinfection.
• the plant disease controlling composition of the present invention can also be used in admixture with other fungicides, insecticides, acaricides, nematocides, herbicides, plant growth regulating agents, fertilizers or soil improvement agents, or used simultaneously with them without mixing.
• active ingredients of such other fungicides include: azole fungicidal compounds such as propiconazole, prothioconazole, triadimenol, prochloraz, penconazole, tebuconazole, flusilazole, diniconazole, bromuconazole, epoxiconazole, difenoconazole, cyproconazole, metconazole, triflumizole, tetraconazole, microbutanil, fenbuconazole, hexaconazole, fluquinconazole, triticonazole, bitertanol, imazalil, flutriafol, simeconazole and ipconazole; cyclic amine fungicidal compounds such as fenpropimorph, tridemorph and fenpropidin; benzimidazole fungicidal compounds such as carbendazim, benomyl, thiabendazole and
• active ingredients of insecticides include the following compounds:
• Organophosphorus compounds acephate, Aluminium phosphide, butathiofos, cadusafos, chlorethoxyfos, chlorfenvinphos, chlorpyrifos, chlorpyrifos-methyl, cyanophos: CYAP 5 diazinon, DCIPCdichlorodiisopropyl ether), dichlofenthion: ECP, dichlorvos: DDVP, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, etrimfos, fenthion: MPP, fenitrothion: MEP, fosthiazate, formothion, Hydrogen phosphide, isofenphos, isoxathion, malathion, mesulfenfos, methidathion: DMTP, monocrotophos, naled: BRP, oxydeprofos: ESP, parathi
• Nereistoxin compounds cartap, bensultap, thiocyclam, monosultap, bisultap, etc.;
• Neonicotinoid compounds imidacloprid, nitenpyram, acetamiprid, thiamethoxam, thiacloprid, dinotefuran, clothianidin, etc.;
• Benzoylurea compounds chlorfluazuron, bistrifluron, diafenthiuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, triazlon, etc.; (7) Phenylpyrazole compounds acetoprole, ethiprole, fipronil, vaniliprole, pyriprole, pyrafluprole, etc.;
• insecticides avermectin-B, bromopropylate, buprofezin, chlorphenapyr, cyromazine, D-D(I, 3-Dichloropropene), emamectin-benzoate, fenazaquin, flupyrazofos, hydroprene, methoprene, indoxacarb, metoxadiazone, milbemycin-A, pymetrozine, pyridalyl, pyriproxyfen, spinosad, sulfluramid, tolfenpyrad, triazamate, flubendiamide, lepimectin, Arsenic acid, benclothiaz, Calcium cyanamide, Calcium polysulfide, chlordane, DDT, DSP, flufenerim, flonicamid, flurimfen, formetanate, metam-ammonium, metam-sodium, Methyl bromide, nid
• active ingredients of acaricides include acequinocyl, amitraz, benzoximate, bifenaate, bromopropylate, chinomethionat, chlorobenzilate,
• CPCBS chlorfenson
• clofentezine cyflumetofen
• kelthane dicofol
• etoxazole fenbutatin oxide
• fenothiocarb fenpyroximate
• fluacrypyrim fluproxyfen
• hexythiazox propargite: BPPS, polynactins, pyridaben, Pyrimidifen, tebufenpyrad, tetradifon, spirodiclofen, spiromesifen, spirotetramat, amidoflumet, and cyenopyrafen.
• active ingredients of nematicides include DCIP, fosthiazate, levamisol hydrochloride, methylisothiocyanate; moraltel tartarate, and imicyafos.
• the plant disease controlling method of the present invention has a step of applying a plant or soil with an effective amount of the compound of the present invention.
• the controlling method of the present invention is usually carried out by applying a plant or soil with the plant disease controlling composition of the present invention.
• the amount of the plant disease controlling composition of the present invention when used in the plant disease controlling method of the present invention varies depending on weather conditions, formulation form, application period, application method, application site, subject disease, subject crop and so on, and the amount of the compound of the present invention in the plant disease controlling composition of the present invention is usually 1 to 500 g, preferably 2 to 200 g per 1000 m 2 .
• the emulsifiable concentrate, wettable powder, flowable and so on are usually diluted with water before application, and in this case, the concentration of the compound of the present invention after dilution is usually 0.0005 to 2 wt%, preferably 0.005 to 1 wt%, and the dust, granule and so on are usually used as they are without dilution.
• the amount of the compound of the present invention in the plant disease controlling composition of the present invention is usually 0.001 to 100 g, preferably 0.01 to 5O g based on 1 kg of the seed.
• the plant disease controlling composition of the present invention can be used as a controlling composition for plant diseases in agricultural grounds such as field, paddy field, turf and orchard.
• the plant disease controlling composition of the present invention is able to control or prevent plant diseases caused by plant diseases in crop lands for cultivating the following "crops".
• Agricultural crops corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, buckwheat, beet, rapeseed, sunflower, sugar cane, tobacco, etc.; vegetables: solanaceous vegetables (eggplant, tomato, bell pepper, pepper, potato, etc.), cucurbitaceous vegetables (cucumber, pumpkin, zucchini, water melon, melon, etc.), cruciferous vegetables (Japanese radish, white turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, leaf mustard, broccoli, cauliflower, etc.), asteraceous vegetables (burdock, crown daisy, artichoke, lettuce, etc.), liliaceous vegetables (green onion, onion, garlic, and asparagus), ammiaceous vegetables (carrot, parsley, celery, parsnip, etc.), chenopodiaceous vegetables (spinach, Swiss chard, etc.), lamiaceous vegetables (Perilla frutescens, mint
• crops include crops, to which resistance to HPPD inhibitors such as isoxaflutole, ALS inhibitors such as imazethapyr and thifensulfuron-methyl, EPSP synthetase inhibitors, glutamine synthetase inhibitors, and herbicides such as bromoxynil, has been imparted by a classical breeding method or genetically engineering technology.
• HPPD inhibitors such as isoxaflutole
• ALS inhibitors such as imazethapyr and thifensulfuron-methyl
• EPSP synthetase inhibitors such as imazethapyr and thifensulfuron-methyl
• EPSP synthetase inhibitors such as imazethapyr and thifensulfuron-methyl
• EPSP synthetase inhibitors such as imazethapyr and thifensulfuron-methyl
• EPSP synthetase inhibitors such as imazethapyr and
• Examples of “crops” to which resistance is imparted by a classical breeding method include Clearfield (registered trademark) canola that is resistant to imidazolinone herbicides such as imazethapyr, and STS soybean that is resistant to sulfonylurea ALS inhibitory herbicides such as thifensulfuron-methyl.
• examples of “crops” to which resistance is imparted by genetic recombination include corn varieties resistant to glyphosate or glufosinate. Such corn varieties have already been on the market with product names such as "RoundupReady (registered trademark)” and "LibertyLink (registered trademark).”
• crops include genetically engineered crops produced using such genetic recombination techniques, which, for example, are able to synthesize selective toxins as known in genus Bacillus.
• toxins expressed in such genetically engineered crops include: insecticidal proteins derived from Bacillus cereus or Bacillus popilliae; ⁇ -endotoxins such as CrylAb, Cryl Ac, CrylF, CrylFa2, Cry2Ab, Cry3A, Cry3Bbl or Cry9C, derived from Bacillus thuringiensis; insecticidal proteins such as VIPl, VIP2, VIP3, or VIP3A; insecticidal proteins derived from nematodes; toxins generated by animals, such as scorpion toxin, spider toxin, bee toxin, or insect-specific neurotoxins; mold fungi toxins; plant lectin; agglutinin; protease inhibitors such as a trypsin inhibitor, a serine protease inhibitor, patatin, cystatin, or a papain inhibitor; ribosome-inactivating proteins (RIP) such as lycine, corn-RIP, abrin, luffin, saporin
• toxins expressed in such genetically recombinant crops also include: hybrid toxins of ⁇ -endotoxin proteins such as CrylAb, Cry IAc, CrylF, CrylFa2, Cry2Ab, Cry 3 A, Cry 3BbI or Cry9C, and insecticidal proteins such as VIPl 5 VIP2, VIP3 or VIP3A; partially deleted toxins; and modified toxins.
• hybrid toxins are produced from a new combination of the different domains of such proteins, using a genetic recombination technique.
• Cry IAb comprising a deletion of a portion of an amino acid sequence has been known.
• a modified toxin is produced by substitution of one or multiple amino acids of natural toxins.
• Toxins contained in such recombinant plants are able to impart resistance particularly to insect pests belonging to Coleoptera, Diptera and Lepidoptera, to the plants.
• genetically recombinant plants which comprise one or multiple insecticidal pest-resistant genes and which express one or multiple toxins, have already been known, and some of such genetically recombinant plants have already been on the market.
• Examples of such genetically recombinant plants include YieldGard (registered trademark) (a corn variety for expressing Cry IAb toxin), YieldGard Rootworm (registered trademark) (a corn variety for expressing Cry3Bbl toxin), YieldGard Plus (registered trademark) (a corn variety for expressing Cry IAb and Cry3Bbl toxins), Herculex I (registered trademark) (a corn variety for expressing phosphinotricine N-acetyl transferase (PAT) so as to impart resistance to CrylFa2 toxin and gluphosinate), NuCOTN33B (a cotton variety for expressing Cry IAc toxin), Bollgard I (registered trademark) (a cotton variety for expressing CrylA
• crops also include crops produced using a genetic engineered technique, which have ability to generate antipathogenic substances having selective action.
• PRPs antipathogenic substances
• EP-A-O 392 225 Such antipathogenic substances and genetically recombinant crops that generate them are described in EP-A-O 392 225, WO 95/33818, EP-A-O 353 191, etc.
• antipathogenic substances expressed in genetically recombinant crops include: ion channel inhibitors such as a sodium channel inhibitor or a calcium channel inhibitor (KPl, KP4 and KP6 toxins, etc., which are produced by viruses, have been known); stilbene synthase; bibenzyl synthase; chitinase; glucanase; a PR protein; and antipathogenic substances generated by microorganisms, such as a peptide antibiotic, an antibiotic having a hetero ring, a protein factor associated with resistance to plant diseases (which is called a plant disease-resistant gene and is described in WO 03/000906).
• ion channel inhibitors such as a sodium channel inhibitor or a calcium channel inhibitor (KPl, KP4 and KP6 toxins, etc., which are produced by viruses, have been known)
• stilbene synthase such as a sodium channel inhibitor or a calcium channel inhibitor
• bibenzyl synthase such as a peptide antibiotic, an antibiotic
• the plant disease controlling method of the present invention is carried out usually by using a plant disease controlling composition of the present invention according to the above-described method for application of the plant disease controlling composition of the present invention.
• Rice plant Magnaporthe grisea, Cochliobolus miyabeanus, Rhizoctonia solani, Gibberella fujikuroi, Sclerophthora macrospora; Wheats, barleys and oats: Erysiphe graminis, Fusarium graminearum, F. avenacerum, F. culmorum, Microdochium nivale, Puccinia striiformis, P. graminis, P. recondita, P. hordei, Typhula sp.,Micronectriella nivalis, Ustilago tritici, U.
• pirina Alternaria alternata Japanese pear pathotype, Gymnosporangium haraeanum; Peach: Monilinia fructicola, Cladosporium carpophilum, Phomopsis sp.; Grape: Elsinoe ampelina, Glomerella cingulata, Uncinula necator, Phakopsora ampelopsidis, Guignardia bidwellii, Plasmopara viticola; Persimmon: Gloeosporium kaki, Cercospora kaki, Mycosphaerella nawae; Gourds Colletotrichum lagenarium, Sphaerotheca fuliginea, Mycosphaerella melonis, Fusarium oxysporum, Pseudoperonospora cubensis, Phytophthora sp., Pythium sp.; Tomato: Alternaria solani, Cladosporium fulvum,
• Strawberry Sphaerotheca humuli
• Tea crop Exobasidium reticulatum, Elsinoe leucospila, Pestalotiopsis sp., Colletotrichum theae-sinensis
• Tobacco Alternaria longipes, Erysiphe cichoracearum, Colletotrichum tabacum, Peronospora tabacina, Phytophthora nicotianae
• Suger beet Cercospora beticola, Thanatephorus cucumeris, Thanatephorus cucumeris, Aphanomyces sochlioides
• Rose Diplocarpon rosae, Sphaerotheca pannosa
• Crysanthemum Septoria chrysanthemi-indici, Puccinia horiana
• Onion Botrytis cinerea, B.
• Botrytis cinerea Sclerotinia sclerotiorum
• Radish Alternaria brassicicola
• Lawns Sclerotinia homeocarpa, Rhizoctonia solani
• Banana Mycosphaerella fijiensis, Mycosphaerella musicola.
• N-benzothiazol-6-yl-2-(2-fluoro-3-hydroxyphenyl)acetamide 0.22 g of 6-bromo-l-hexene and 5 ml of DMF was added 0.43 g of cesium carbonate. The mixture was stirred at room temperature for 4 hours. Ice water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline solution, then, dried over magnesium sulfate and concentrated under reduced pressure.
• the resultant residue was subjected to silica gel column chromatography and concentrated to obtain a residue which was washed with hexane, and 0.09 g of N-benzothiazol- 6-yl-2-(2-fluoro-3-(5-hexenyloxy)phenyl)acetamide (hereinafter, referred to as the present compound (2)) was obtained.
• the present compound (2) N-benzothiazol- 6-yl-2-(2-fluoro-3-(5-hexenyloxy)phenyl)acetamide
• the resultant residue was concentrated to obtain a residue which was washed with hexane, and 0.16 g of N-benzothiazol-6-yl-2-(2-fluoro.-3- (2-pentenyloxy)phenyl)acetamide (hereinafter, referred to as the present compound (3)) was obtained.
• the present compound (3) N-benzothiazol-6-yl-2-(2-fluoro.-3- (2-pentenyloxy)phenyl)acetamide
• the resultant solid was washed sequentially with a sodium hydroxide aqueous solution, water and hexane, and 0.19 g of N-benzothiazol-6- yl-2-(3-(5-hexenyloxy)phenyl)acetamide (hereinafter, referred to as the present compound (6)) was obtained.
• the present compound (6) N-benzothiazol-6- yl-2-(3-(5-hexenyloxy)phenyl)acetamide
• the resultant solid was washed sequentially with a sodium hydroxide aqueous solution, water and hexane, and 0.20 g of N-benzothiazol-6- yl-2-(3-(7-octenyloxy)phenyl)acetamide (hereinafter, referred to as the present compound (7)) was obtained.
• the present compound (7) N-benzothiazol-6- yl-2-(3-(7-octenyloxy)phenyl)acetamide
• the resultant solid was washed sequentially with a sodium hydroxide aqueous solution, water and hexane, and 0.17 g of N-benzothiazol- 6-yl-2-(3-(2-propynyloxy)phenyl)acetamide (hereinafter, referred to as the present compound (12)) was obtained.
• the present compound (12) N-benzothiazol- 6-yl-2-(3-(2-propynyloxy)phenyl)acetamide
• the resultant solid was washed sequentially with a sodium hydroxide aqueous solution, water and hexane, and 0.15 g of N-benzothiazol- 6-yl-2-(3-(4-pentynyloxy)phenyl)acetamide (hereinafter, referred to as the present compound (13)) was obtained.
• the present compound (13) N-benzothiazol- 6-yl-2-(3-(4-pentynyloxy)phenyl)acetamide
• reaction mixture was cooled down to room temperature, then, water was added and the deposited solid was agglomerated and washed sequentially with a sodium hydroxide aqueous solution, water and hexane, and 0.16 g of N-benzothiazol-6-yl-2-(3-(5-hexynyloxy)phenyl)acetamide (hereinafter, referred to as the present compound (14)) was obtained.
• the resultant solid was washed sequentially with a sodium hydroxide aqueous solution, water and hexane, and 0.23 g of N-benzothiazol- 6-yl-2-(3-(2-butynyloxy)phenyl)acetamide (hereinafter, referred to as the present compound (15)) was obtained.
• the present compound (15) N-benzothiazol- 6-yl-2-(3-(2-butynyloxy)phenyl)acetamide
• the resultant solid was washed sequentially with a sodium hydroxide aqueous solution, water and hexane, and 0.23 g of N-benzothiazol- 6-yl-2-(3-(2-pentynyloxy)phenyl)-acetamide (hereinafter, referred to as the present compound (16)) was obtained.
• the present compound (16) N-benzothiazol- 6-yl-2-(3-(2-pentynyloxy)phenyl)-acetamide
• the resultant residue was subjected to silica gel column chromatography, and 0.16 g of N-benzothiazol-6-yl-2-(3 -(6-hepteny loxy)phenyl)acetamide (hereinafter, referred to as the present compound (17)) was obtained.
• the present compound (17) N-benzothiazol-6-yl-2-(3 -(6-hepteny loxy)phenyl)acetamide
• Each of 20 parts of the present compound (1) to (17) and 1.5 parts of sorbitan trioleate were mixed with 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol, and the mixture was finely ground by a wet grinding method, then, into this was added 40 parts of an aqueous solution containing 0.05 parts of xanthan gum and 0.1 part of aluminium magnesium silicate, and further, 10 parts of propylene glycol was added and mixed by stirring, to obtain a flowable.
• Test Examples will show that the compound of the present invention is useful for controlling a plant disease.
• the controlling effect was evaluated by visually observing the area of a disease spot on a subject plant in investigation, and comparing the area of a disease spot of a plant treated with a compound of the present invention with the area of a disease spot of a none-treated plant.
• the present compounds (1), (7), (4) to (15) and (16) were formulated according to Preparation Example 6, and the formulations were diluted with water so that the concentration of active ingredients was 500 ppm. This dilute liquid was sprayed on stem and leaves so as to adhere sufficiently to the leaf surface of the cucumber. After spraying, the plant was air-dried, and PDA medium containing mycelia of Sclerotinia sclerotiorum was placed on the leaf surface of the cucumber. After inoculation, this was left for 4 days at 18°C under humid condition, then, the disease spot area was checked. As a result, the disease spot areas on the plants treated with the present compounds (1), (7), (4) to (15) and (16) were 10% or less of the disease spot area on the none-treated plant. Test Example 2
• the present compound (3) was formulated according to Preparation Example 6, and the formulations were diluted with water so that the concentration of active ingredients was 200 ppm. This dilute liquid was sprayed on stem and leaves so as to adhere sufficiently to the leaf surface of the cucumber. After spraying, the plant was air-dried, and PDA medium containing mycelia of Sclerotinia sclerotiorum was placed on the leaf surface of the cucumber. After inoculation, this was left for 4 days at 18°C under humid condition, then, the disease spot area was checked. As a result, the disease spot areas on the plants treated with the present compound (3) was 10% or less of the disease spot area on the none-treated plant.
• the present compound (5) and (13) were formulated according to Preparation Example 6, and the formulations were diluted with water so that the concentration of active ingredients was 500 ppm. This dilute liquid was sprayed on stem and leaves so as to adhere sufficiently to the leaf surface of the cucumber. After spraying, the plant was air-dried, and PDA medium containing spores of Botrytis cinerea was placed on the leaf surface of the cucumber. After inoculation, this was left for 5 days at 12 0 C under humid condition, then, the disease spot area was checked. As a result, the disease spot areas on the plants treated with the present compounds (5) and (13) were 10% or less of the disease spot area on the none-treated plant. Test Example 4
• Plastic pots were stuffed with seedbed soil, rice plant (plant variety; Nihonbare) was sowed on this, and allowed to grow in a greenhouse for 12 days.
• the present compounds (4), (8), (12) and (15) were formulated according to Preparation Example 6, and the formulations were diluted with water so that the concentration of active ingredients was 500 ppm. This dilute liquid was sprayed on stem and leaves so as to adhere sufficiently to the leaf surface of the rice plant. After spraying, the plant was air-dried, and pots having leaves affected by Magnaporthe grisea were allowed to stand still around the sprayed plant. All rice plants were placed under humid condition only in night, and 5 days after inoculation, the disease spot area was checked. As a result, the disease spot areas on the plants treated with the present compounds (4), (8), (12) and (15) were 10% or less of the disease spot area on the none-treated plant.
• the compound of the present invention is useful as an active ingredient of a plant disease controlling composition since the compound has a plant disease controlling effect.

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