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WO2009088070A1 - Dérivé de (méthyl hétérocyclique)azolylméthylcyclopentanol et son intermédiaire, procédé de fabrication du dérivé et préparation pour l'agriculture ou l'horticulture et agent protecteur pour une substance industrielle comprenant chacun le dérivé - Google Patents

Dérivé de (méthyl hétérocyclique)azolylméthylcyclopentanol et son intermédiaire, procédé de fabrication du dérivé et préparation pour l'agriculture ou l'horticulture et agent protecteur pour une substance industrielle comprenant chacun le dérivé Download PDF

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WO2009088070A1
WO2009088070A1 PCT/JP2009/050201 JP2009050201W WO2009088070A1 WO 2009088070 A1 WO2009088070 A1 WO 2009088070A1 JP 2009050201 W JP2009050201 W JP 2009050201W WO 2009088070 A1 WO2009088070 A1 WO 2009088070A1
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group
derivative
heterocyclic
substituted
methyl
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Japanese (ja)
Inventor
Atsushi Ito
Keiichi Sudo
Eiyu Imai
Takashi Shimokawara
Toshihide Saishoji
Masaru Mori
Rie Kimura
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Kureha Corp
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Kureha Corp
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/08—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing alicyclic rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/08—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing alicyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/08—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing alicyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/08—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing alicyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/08—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing alicyclic rings

Definitions

  • the present invention relates to a (heterocyclic methyl) azolylmethylcyclopentanol derivative and an intermediate thereof, a production method thereof, and an agricultural and horticultural drug and an industrial material protective agent containing this derivative as an active ingredient.
  • Patent Document 1 discloses a structure in which an azolylmethyl group and a substituted benzyl group are bonded to adjacent carbon atoms on the cyclopentane ring.
  • Azole derivatives having the following are disclosed:
  • Patent Document 2 discloses an azole derivative having a structure in which an azolylmethyl group and a cycloalkyl group or a cycloalkylmethyl group are bonded to adjacent carbon atoms on a cyclopentane ring.
  • Japanese Patent Publication No. 6-25140 Japanese Patent Laid-Open No. 2-145576
  • the present invention provides a novel (heterocyclic methyl) azolylmethylcyclopentanol derivative useful as an antibacterial active ingredient for agricultural and horticultural agents, and the (heterocyclic methyl) azolylmethylcyclopentanol derivative as an active ingredient.
  • the main purpose is to provide a contained agricultural and horticultural chemical.
  • the present invention first provides a (heterocyclic methyl) azolylmethylcyclopentanol derivative represented by the chemical formula (I). *
  • R 1 and R 2 represent a hydrogen atom or a C1-C5 alkyl group.
  • R 3 represents a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted condensed heterocyclic group. Represents a nitrogen atom or a methine group.
  • the present invention provides an agricultural and horticultural agent characterized by containing a (heterocyclic methyl) azolylmethylcyclopentanol derivative represented by the chemical formula (I) as an active ingredient.
  • the present invention provides an industrial material protective agent characterized by containing this derivative as an active ingredient.
  • this invention is represented by Chemical formula (I) including the process of adding the azole ring of Chemical formula (VII) to the epoxy group of the oxaspiro heptane derivative represented by Chemical formula (V) in presence of a base.
  • a method for producing a (heterocyclicmethyl) azolylmethylcyclopentanol derivative is provided. (Wherein R 1 and R 2 represent a hydrogen atom or a C1-C5 alkyl group.
  • R 3 represents a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted condensed heterocyclic group.
  • A represents a nitrogen atom or a methine group.
  • This production method may further include a step of obtaining the oxaspiroheptane derivative from the cyclopentanone derivative represented by the chemical formula (IV).
  • R 1 and R 2 represent a hydrogen atom or a C1-C5 alkyl group.
  • R 3 represents a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted condensed heterocyclic group.
  • the present invention also provides an oxaspiroheptane derivative represented by the chemical formula (V) and a cyclopentanone derivative represented by the chemical formula (IV).
  • R 1 and R 2 represent a hydrogen atom or a C1-C5 alkyl group.
  • the alkyl group of C1 to C5 may be any of primary, secondary, and tertiary, for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s- Examples thereof include a butyl group, a cyclopropylmethyl group, a t-butyl group, an n-pentyl group, an isopentyl group, and a neopentyl group.
  • R 3 represents a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted condensed heterocyclic group.
  • the heterocyclic group include 3- to 8-membered saturated or unsaturated heterocyclic groups containing 1 to 4 atoms selected from the group consisting of oxygen atom, sulfur atom and nitrogen atom. A 5- or 6-membered heterocyclic group is preferable.
  • the fused heterocyclic group include 8- to 10-membered fused heterocyclic groups containing 1 to 4 of at least one atom selected from the group consisting of an oxygen atom, a sulfur atom and a nitrogen atom. Or the condensed heterocyclic group which the 6-membered heterocyclic ring condensed is preferable.
  • the 5-membered or 6-membered heterocyclic group include a furyl group, a tetrahydrofuryl group, a thienyl group, a pyrrolyl group, a pyrrolinyl group, a pyrrolidinyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, and an imidazolyl group.
  • Imidazolinyl group imidazolidinyl group, pyrazolyl group, pyrazolinyl group, pyrazolidinyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, tetrazolyl group and other 5-membered heterocyclic groups, pyranyl group, pyridyl group, piperidinyl group, dioxanyl group, oxazinyl group, Examples thereof include 6-membered heterocyclic groups such as morpholinyl group, thiazinyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, piperazinyl group, and triazinyl group.
  • Preferable examples of the 5-membered or 6-membered heterocyclic group include a furyl group, a thienyl group, a thiazolyl group, a pyridyl group, and a pyridazinyl group.
  • condensed heterocyclic group in which a 5- or 6-membered heterocyclic ring is condensed include a benzofuranyl group, an isobenzofuranyl group, a dihydrobenzofuranyl group, a dihydroisobenzofuranyl group, a benzothienyl group, and an isobenzothienyl group.
  • the substituent that the heterocyclic group or the condensed heterocyclic group has is not particularly limited, and examples thereof include halogeno groups such as a fluoro group, a chloro group, a bromo group, and an iodo group, a C1-C4 alkyl group, and a C1-C4 group.
  • halogeno groups such as a fluoro group, a chloro group, a bromo group, and an iodo group, a C1-C4 alkyl group, and a C1-C4 group.
  • Examples of the substituent of the phenoxy group or the phenyl group include a halogeno group such as a fluoro group, a chloro group, a bromo group, and an iodo group, a C1 to C4 alkyl group, a C1 to C4 halogenated alkyl group, and a C1 to C4 group.
  • Examples include C4 alkoxy groups.
  • the number of substituents of the heterocyclic group or the condensed heterocyclic group and the phenoxy group or the phenyl group is not particularly limited, and one or a plurality of places may be substituted. Substitution is preferred. When the number of substitutions is 2 or more, they may be substituted with the same substituent or may be substituted with different substituents.
  • the position of the substituent in the case where the heterocyclic group or the condensed heterocyclic group, and the phenoxy group or the phenyl group have a substituent is not particularly limited.
  • A represents a nitrogen atom or a methine group.
  • the (heterocyclic methyl) azolylmethylcyclopentanol derivative according to the present invention may have geometric isomers and optical isomers due to the presence of asymmetric carbon in the cyclopentane skeleton.
  • Compound (I) includes isomers and mixtures of each isomer in any ratio.
  • the (heterocyclic methyl) azolylmethylcyclopentanol derivative according to the present invention has low toxicity to humans and the like and is highly safe in handling. In addition, it exhibits excellent agricultural and horticultural disease control effects on a wide range of plant diseases, plant growth control effects and industrial material protection effects.
  • FIG. 1 is a conceptual diagram for explaining an example of a method for producing a (heterocyclic methyl) azolylmethylcyclopentanol derivative of the formula (I) It is.
  • An example of a preferred method for producing the (heterocyclicmethyl) azolylmethylcyclopentanol derivative according to the present invention will be described below with reference to the drawings.
  • the (heterocyclic methyl) azolylmethylcyclopentanol derivative of the chemical formula (I) obtained by the following production method should be appropriately selected depending on the compounds of the formulas (II) to (VII) used and reaction conditions. Shall be able to.
  • R 1 , R 2 , R 3 and A are the same as described above.
  • a heterocyclic methyl group (VI) is introduced into a ketoester derivative represented by the formula (II) to obtain a heterocyclic ketoester derivative (III) (first step).
  • the heterocyclic ketoester derivative is derived into a cyclopentanone derivative represented by the formula (IV) (second step).
  • An oxaspiroheptane derivative represented by the formula (V) is synthesized from the cyclopentanone derivative (third step), and then an azole ring represented by the formula (VII) is added to the oxaspiroheptane derivative.
  • a (heterocyclicmethyl) azolylmethylcyclopentanol derivative of the formula (I) fourth step.
  • the heterocyclic ketoester derivative represented by the formula (III) is obtained by alkylating the 1-position of the ketoester derivative represented by the formula (II) with a base and a heterocyclic methyl halide (VI).
  • the solvent to be used is not particularly limited, but a polar organic solvent is preferably used.
  • the reaction temperature in the first step is not particularly limited and can be set in a temperature range from room temperature to the boiling point of the solvent used, but is preferably 20 to 100 ° C.
  • ketoester derivative represented by the formula (II) which is the starting material in the first step can be synthesized by a conventionally known method.
  • a specific method for example, J. Org. Med. Chem. 29, 411 (1986) and J. Org. Org. Chem. 29, 2781 (1964).
  • the cyclopentanone derivative represented by the formula (IV) can be obtained by hydrolyzing and decarboxylating the heterocyclic ketoester derivative represented by the formula (III). This hydrolysis and decarboxylation reaction can be performed under both basic and acidic conditions.
  • the solvent used is not particularly limited, but it is desirable to use a mixed solvent of water, lower alcohol and aromatic hydrocarbon.
  • the base used is not particularly limited, but sodium hydroxide or potassium hydroxide is preferably used.
  • the reaction temperature at this time is not particularly limited, but is preferably 40 ° C. to the reflux point, more preferably 70 ° C. to the reflux point.
  • the solvent used is not particularly limited, but it is preferable to use acetic acid as a solvent in addition to water.
  • an inorganic acid such as hydrochloric acid or hydrobromic acid is used.
  • the reaction temperature at this time is not particularly limited, but is preferably 50 ° C. to the reflux point, more preferably 80 ° C. to the reflux point.
  • the oxaspiroheptane derivative represented by the formula (V) is cyclized by adding a methylene group to the carbonyl group of the cyclopentanone derivative represented by the formula (IV) by sulfonium methylide or oxosulfonium methylide. Or after converting the carbonyl group to a methylene group, the methylene group is oxidized, or iodohydrin obtained by combining metal samarium and diiodomethane is cyclized by alkali treatment.
  • conventionally known methods can be used. For example, the methods described in JP-B-6-25140 and JP-A-5-271197 can be used.
  • the (heterocyclic methyl) azolylmethylcyclopentanol derivative of the formula (I) is bonded to the azole group of the formula (VII) in the presence of a base on the epoxy group of the oxaspiroheptane derivative of the formula (V).
  • the base used is not particularly limited, but sodium hydride and potassium carbonate are preferably used.
  • the solvent used in this step is not particularly limited, but an organic solvent, particularly an aprotic polar solvent such as dimethylformamide (DMF), dimethylacetamide, N-methylpyrrolidone, etc. is preferably used.
  • the reaction temperature in this step is not particularly limited, but is preferably in the range of 0 ° C to 100 ° C.
  • the (heterocyclic methyl) azolylmethylcyclopentanol derivative according to the present invention is suitably used as an active ingredient of agricultural and horticultural agents.
  • the agricultural and horticultural chemicals containing the (heterocyclic methyl) azolylmethylcyclopentanol derivative as an active ingredient will be described below.
  • the (heterocyclic methyl) azolylmethyl cyclopentanol derivative based on this invention shows the plant growth control effect which adjusts growth with respect to a wide range of crops and horticultural plants, and increases a yield and quality.
  • crops include: Wheat, barley, buckwheat and other barley, rice, rapeseed, sugar cane, corn, maize, soybeans, peas, peanuts, sugar beet, cabbage, garlic, radish, carrot, apple, pear, mandarin orange, orange, lemon and other citrus fruits, Peach, cherry peach, avocado, mango, papaya, capsicum, cucumber, melon, strawberry, tobacco, tomato, eggplant, turf, chrysanthemum, azalea and other ornamental plants.
  • the form in which the (heterocyclic methyl) azolylmethylcyclopentanol derivative according to the present invention is used as an active ingredient of an agricultural and horticultural disease control agent is not particularly limited.
  • it may be used alone without any other components.
  • it may be mixed with a solid carrier, a liquid carrier, a surfactant, and other formulation adjuvants to be used in various forms such as powders, wettable powders, granules and emulsions.
  • the (heterocyclic methyl) azolylmethylcyclopentanol derivative according to the present invention is used as an active ingredient in these preparations in an amount of 0.1 to 95% by weight, more preferably 0.5 to 90% by weight, It is preferable to formulate it so as to contain 2 to 80% by weight.
  • the substance used as the formulation adjuvant is not particularly limited, and can be appropriately selected in consideration of the purpose of use and desired effect.
  • Suitable carriers, diluents, surfactants and the like are exemplified below. .
  • solid carrier talc, kaolin, bentonite, diatomaceous earth, white carbon, clay and the like can be used.
  • liquid diluent water, xylene, toluene, chlorobenzene, cyclohexane, cyclohexanone, dimethyl sulfoxide (DMSO), dimethylformamide, alcohol or the like can be used.
  • DMSO dimethyl sulfoxide
  • the surfactant is preferably used depending on its effect, and polyoxyethylene alkylaryl ether, polyoxyethylene sorbitan monolaurate, or the like can be used as an emulsifier.
  • polyoxyethylene alkylaryl ether, polyoxyethylene sorbitan monolaurate, or the like can be used as an emulsifier.
  • dispersant lignin sulfonate, dibutyl naphthalene sulfonate, or the like can be used.
  • As the wetting agent an alkyl sulfonate, an alkyl phenyl sulfonate, or the like can be used. Since this compound contains a 1,2,4-triazole group or an imidazole group, it can be used in the form of an inorganic acid salt, an organic acid salt or a metal complex.
  • the method for using the agricultural and horticultural chemical according to the present invention is not particularly limited. For example, it may be used as it is, diluted to a predetermined concentration with a diluent such as water, or a plurality of types.
  • a diluent such as water, or a plurality of types.
  • the (heterocyclic methyl) azolylmethylcyclopentanol derivative according to the present invention may be mixed.
  • the concentration of the (heterocyclic methyl) azolylmethylcyclopentanol derivative according to the present invention when diluted is preferably in the range of 0.001 to 1.0%.
  • the amount of the (heterocyclic methyl) azolylmethylcyclopentanol derivative according to the present invention is 20 to 5000 g, more preferably 50 to 1000 g, per 1 ha of agricultural or horticultural land such as fields, fields, orchards and greenhouses. . Since these use concentrations and amounts vary depending on the dosage form, use time, use method, use place, target crop, etc., it is of course possible to increase or decrease without limiting to the above range.
  • the (heterocyclic methyl) azolylmethylcyclopentanol derivative according to the present invention is combined with other active ingredients such as other fungicides, insecticides, acaricides, herbicides, plant growth regulators, fertilizers, etc. Can also be used.
  • ⁇ Fungicide> Acibenzolar S methyl, 2-phenylphenol (OPP), azaconazole, azoxystrobin, amisulbrom, bixaphene, benalaxyl, benomyl, bench avaricarb-isopropyl, bicarbonate, biphenyl, viteltanol, blasticidin-S, borax, bordeaux, boscalid, Bromuconazole, bronopol, bupirimate, secbutyramine, calcium polysulfide, captafor, captan, carbendazim, carboxin, carpropamide, quinomethionate, chloronebu, chloropicrin, chlorothalonil, clozolinate, cyazofamide, cyflufenamide, simoxanil, cyproconil, cyprodiazole Dazomet, debacarb, diclofuranide, diclocimet, dichrome , Dichlorane, dieth
  • ⁇ Insecticide / Acaricide> Abamectin, Acephate, Acrinathrin, Alanicarb, Aldicarb, Alletrin, Amitraz, Avermectin, Azadirachtin, Azamethifos, Azinphos-ethyl, Azinphos-methyl, Azocycline, Bacillus filmus, Bacillus subtilis, Bacillus thuringibulbbenthulbenbencarb , Benzoxymate, Bifenazite, Bifenthrin, Bioallethrin, Bioresmethrin, Bistriflurone, Buprofezin, Butocaboxin, ButoxyCarboxin, Kazusafos, Carbaryl, Carbofuran, Carbosulfan, Cartap, CGA 50439, Chlordein, Chloretifos, Chlorphenapal Chlorfenvin foss, chlorfluazuron ,
  • ⁇ Plant growth regulator Ansimidol, 6-benzylaminopurine, paclobutrazole, diclobutrazole, uniconazole and the like.
  • the (heterocyclic methyl) azolylmethylcyclopentanol derivative according to the present invention exhibits an excellent effect of protecting the material from a wide range of harmful microorganisms that attack the industrial material.
  • microorganisms include the following. Aspergillus sp., Trichoderma sp., Penicillium sp., Geotrichum sp., Chaetomium sp., Cadhola (Cadophora sp.), Ceratostomella sp., Cladosporium sp., Corticium sp., Lentinus sp., Lenzites sp., Forma sp.
  • Polysticus sp. Pullularia sp., Stereum sp., Trichosporium sp., Aerobacter sp., Bacillus sp., Desulfobibrio (Desulfovibrio sp.), Pseudomonas sp., Flavobacterium sp., Micrococcus sp.).
  • Aspergillus sp. Penicillium Chsp., Ketotomium sp., Myrothecium sp., Curvularia sp., Gliomastixsp., Mennoniella Memnoniella sp.), Sarcopodium sp., Stschybotryssp., Stemphylium S., Zygorhynchus sp., Bacillus sp., Staphylococcus. Such.
  • Wood-modifying fungi Wood-modifying fungi, Tyromyces palustris, Kawariotake (Coriolus versicolor), Aspergillus sp., Penicillium sp., Rhizopussp., Aureobasidium sp., Aureobasidium sp. (Gliocladum sp.), Cladosporium sp., Ketomium (Spae), Trichodermasp.
  • Aspergillus sp. Penicillium sp., Ketomium (Chaetomiumsp.), Cladosporium sp., Mucor sp., Paecilomycessp., Pilobus (Pilobus) sp.), pullularia (Pullulariasp.), trichosporon (Trichosporon sp.), trichothecium (Tricothecium sp.), rubber and plastic-degrading microorganisms such as Aspergillus (sp.), Penicillium (Penicilliumsp.), Rhizopus sp.
  • Trichodermasp. Ketomium (Chaetomium sp.), Myrotheciumsp., Streptomyces sp., Pseudomonas sp., Bacillus sp., Micrococcus sp. , Sererratiasp., Margarinomyces s sp.), Monascus sp.
  • Aspergillus sp. Penicillium sp., Cladosporium sp., Aureobasidium sp., Gliocladium sp., Botrio dipro Deer (Botryodiplodiasp.), Macrosporum (Macrosporium sp.), Monilia (Monilia sp.), Forma (Phoma sp.), Pullularia ((Pullularia sp.), Sporotrichumsp.), Trichoderma sp., Bacillus (Proteus sp.), Pseudomonas sp., Serratia sp.
  • the (heterocyclic methyl) azolylmethylcyclopentanol derivative according to the present invention can be used alone as an industrial material protective agent, it is usually dissolved or dispersed in a liquid carrier, or mixed with a solid carrier, and if necessary, an emulsifier , Dispersing agents, spreading agents, penetrating agents, wetting agents, stabilizers, etc. are added and formulated into various forms such as wettable powders, powders, granules, tablets, pastes, suspensions, sprays, etc. .
  • the (heterocyclic methyl) azolylmethylcyclopentanol derivative according to the present invention is used as an active ingredient in an amount of 0.1 to 95% by weight, more preferably 0.5 to 90% by weight, and even more preferably 2%. Contains up to 80% by weight.
  • Carriers used as formulation adjuvants include, as liquid carriers, water, alcohols (eg, methyl alcohol, ethyl alcohol, ethylene glycol, cellosolve, etc.), ketones (eg, acetone, methyl ethyl ketone, etc.), ethers (eg, Dimethyl ether, diethyl ether, dioxane, tetrahydrofuran, etc.), aromatic hydrocarbons (eg, benzene, toluene, xylene, methylnaphthalene, etc.), aliphatic hydrocarbons (eg, gasoline, kerosene, kerosene, machine oil, fuel oil, etc.) Acid amides (eg, dimethylformamide, N-methylpyrrolidone, etc.), halogenated hydrocarbons (eg, chloroform, carbon tetrachloride, etc.), esters (eg, ethyl acetate, glycerin esters of fatty
  • fine powders or granular materials such as kaolin clay, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, urea, ammonium sulfate can be used.
  • emulsifiers and dispersants used as formulation adjuvants include soaps, alkylsulfonic acids, alkylarylsulfonic acids, dialkylsulfosuccinic acids, quaternary ammonium salts, oxyalkylamines, fatty acid esters, polyalkylene oxides, anhydrosorbitol Surfactants such as systems can be used.
  • the concentration of the (heterocyclic methyl) azolylmethylcyclopentanol derivative according to the present invention when used after dilution varies depending on the dosage form and purpose of use, but is 0.005 to 5% by weight, preferably 0.01 to 1% by weight. It is preferable to adjust by adding a solvent, a diluent, an extender or the like as appropriate.
  • the (heterocyclic methyl) azolylmethylcyclopentanol derivative according to the present invention should be formulated in combination with a fungicide, insecticide, acaricide, anti-degradation agent, etc., similar to the agricultural and horticultural agents described above. You can also. Thereby, the performance as an industrial material protective agent can be improved.
  • the agricultural and horticultural agents according to the present invention include those containing these isomers alone or as a mixture as active ingredients.
  • the agricultural and horticultural agent containing the (heterocyclic methyl) azolylmethylcyclopentanol derivative according to the present invention as an active ingredient can be used for foliage spraying, soil treatment, seed treatment, etc. to plant disease occurrence sites. .
  • ⁇ Measurement equipment> For the nuclear magnetic resonance spectrum (NMR) measurement, a Fourier transform nuclear magnetic resonance apparatus (400 MHz) was used, and tetramethylsilane (TMS) was used as an internal standard. The chemical shift delta ⁇ was expressed in ppm. The coupling constant J is expressed in hertz (Hz). The notations d, t, q, and m represent d (doublet), t (triplet), q (quadlet), and m (multiplet), respectively.
  • IR infrared absorption spectrum
  • IR infrared absorption spectrum
  • IR infrared spectrophotometer was used, and the solid substance was measured as a KBr disk. The wavelength unit is wave number (cm ⁇ 1 ).
  • R 1 and R 2 represent a hydrogen atom or a C1-C5 alkyl group.
  • R 3 represents a substituted or unsubstituted heterocyclic group or a substituted or unsubstituted condensed heterocyclic group. Represents a nitrogen atom or a methine group.
  • R 1 , R 2 and R 3 respectively correspond to R 1 , R 2 and R 3 in the formula (I).
  • R 1 , R 2 and R 3 respectively correspond to R 1 , R 2 and R 3 in the formula (I).
  • a wettable powder was prepared by pulverizing and mixing 50 parts by weight of Compound 3, 50 parts by weight of lignin sulfonate, 3 parts by weight of alkyl sulfonate, and 42 parts by weight of diatomaceous earth, and diluted with water for use.
  • ⁇ Test Example 1> A test was conducted on the control effect of wheat powdery mildew. Compounds of the present invention 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 26, 27, 28, 29, 30, 31, 32, 33 were used, and the wettable powder formulated according to the method of Formulation Example 2 was diluted and suspended in water to a predetermined concentration (100 mg / l). A ratio of 100 liters / 10a (Earl) to 1 to 2 leaf stage wheat (variety: Norin 64) grown using a square plastic pot (size: 6.4 cm ⁇ 6.4 cm) Scattered with.
  • the sprayed leaves were air-dried and then sprinkled with wheat powdery mildew spores on the diseased leaves and managed in a greenhouse (temperature: 20-24 ° C., relative humidity: 20-70 RH).
  • a greenhouse temperature: 20-24 ° C., relative humidity: 20-70 RH.
  • the morbidity was investigated based on the survey criteria shown in Table 10, and the control value of each compound was calculated according to the formula (1).
  • ⁇ Test Example 2> A test was conducted on the control effect of wheat red rust. Compounds of the present invention 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 26, 27, 28, 29, 30, 31, 32, 33 were used, and the wettable powder formulated according to the method of Formulation Example 2 was diluted and suspended in water to a predetermined concentration (100 mg / l). This suspension was sprayed at a rate of 100 liters / 10a (Earl) to 1 to 2 leaf wheat (variety: Abukumawase) grown using a square plastic pot (size: 6.4 cm ⁇ 6.4 cm). did.
  • Earl 100 liters / 10a
  • the sprayed leaves were air-dried and then spray-inoculated with a suspension of wheat red rust fungus summer spores collected from the diseased leaves and kept at 23-25 ° C. under high humidity conditions for 24 hours. After that, it was left in a glass greenhouse (temperature: 20 to 24 ° C., relative humidity: 20 to 70 RH), and on the 10th day after inoculation, the morbidity was investigated for 10 tubes according to the survey criteria shown in Table 11, The control value was calculated from the average morbidity by the above formula (1).
  • ⁇ Test Example 3> It tested about the control effect of green beans mold.
  • Compounds of the present invention 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 26, 27, 28, 29, 30, 31, 32, 33 were used, and the wettable powder formulated according to the method of Formulation Example 2 was diluted and suspended in water to a predetermined concentration (100 mg / l).
  • This suspension was cultivated in an unglazed pot (three-size bowl) with a diameter of 9 cm to the green beans (variety: real gold) at the time of the first true leaf at a rate of 100 liters / 10a (Earl) with a spray gun. Scattered.
  • Example 4 The effect of seed treatment on the control of wheat powdery mildew was examined.
  • Compounds of the present invention 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 26, 2 mg each of 27, 28, 29, 30, 31, 32, and 33 was weighed and dissolved in 18 ⁇ l of DMSO. This was smeared in a vial on each 1 g wheat seed.
  • 1/10 000a pots were seeded with wheat seeds subjected to the above treatment at a rate of 10 grains / pot and cultivated in the greenhouse with lower water supply.
  • diseased wheat seedlings were placed as an inoculum and kept in an infectious state at all times.
  • the morbidity was investigated according to the survey criteria shown in Table 13, and the control value was calculated by the above formula (1). Based on the control value of the treated group at the time when the untreated group became morbidity level 3 or more, it was set as the “powder control index” according to the criteria shown in Table 14.
  • control value is rounded off to the nearest decimal place.
  • the compounds 2, 5, 9, 14, 15, 21, 22, 23, 24, 26, 27, 28, 29, 31, and 32 have a control index of 3 or more against foliar powdery mildew in seed treatment. Indicated. *
  • Tests were conducted on the antibacterial activity of various plant pathogens and industrial material pests of gray mold, rice seedling fungus, wheat red mold, and wheat wilt.
  • Compounds of the present invention 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 26, 1 mg each of 27, 28, 29, 30, 31, 32, and 33 was weighed and dissolved in 2 ml of DMSO. 0.6 ml of this solution was added to 60 ml of PDA medium (potato-dextrose agar medium) at around 60 ° C.
  • a plate medium containing the compound of the present invention having a final concentration of 5 mg / l.
  • a test bacterium previously cultured on a plate medium was punched out with a cork borer having a diameter of 4 mm and inoculated on the drug-containing plate medium. After inoculation, the cells are cultured for 2 to 3 days at a suitable temperature for growth of each bacterium (for example, reference can be made to the literature LIST OF CULTURES 1996 microorganisms 10th edition Foundation Fermentation Research Institute). Was measured by the diameter of the fungus. From the obtained result and the fungus diameter on the untreated flat plate, the hyphal elongation suppression rate was calculated by the formula (2). The calculated mycelial elongation inhibition rate was evaluated in five stages according to the criteria shown in Table 15.
  • R represents the rate of inhibition of hyphal elongation (%)
  • dc represents the diameter of the fungus on the untreated plate
  • dt represents the diameter of the fungus on the treated plate.
  • the active ingredient concentration is 5 mg / l and the compounds 2, 5, 8, 9, 10, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22 , 29, 30, 31, and 33 showed a mycelium elongation inhibitory effect having a high evaluation of 5.
  • the active ingredient concentration is 5 mg / l
  • the compounds 2, 5, 8, 9, 10, 13, 14, 15, 16, 17, 19, 20, 21, 29, 30, 31, and 33 showed a high mycelial elongation inhibitory effect of evaluation 5.
  • the active ingredient concentration is 5 mg / l
  • the compounds 2, 5, 8, 9, 10, 13, 14, 15, 16, 17, 19, 20, 21, 33 are A high hyphal elongation suppression effect of evaluation 5 was shown. *
  • the active ingredient concentration is 5 mg / l, and the compounds 8, 10, 13, 14, 15, 16, 17, 19, 20, 21, 29, 30, 31, 33 are A high hyphal elongation suppression effect of evaluation 5 was shown.
  • Wheat chief prevention test A test was conducted to determine the effect of wheat chief.
  • Compounds of the present invention 1,2,3,4,5,6,7,8,9,10,13,14,15,16,17,18,19,20,21,22,23,24,26, 2 mg each of 27, 28, 29, 30, 31, 32, and 33 was weighed and dissolved in 18 ⁇ l of DMSO. This was smeared in a vial on each 1 g wheat seed.
  • 1 / 10000a pot was seeded with the above-treated wheat seeds at a rate of 10 grains / pot and cultivated in the greenhouse with lower water supply.
  • Ten days after the sowing the plant height of the seedlings in each treatment area was investigated at 10 locations, and the plant height suppression rate was determined by the following formula.
  • R 100 (hc ⁇ ht) / hc (In the formula, “R” represents the plant height inhibition rate (%), “hc” represents the average plant height of the untreated group, and “ht” represents the average plant height of the group treated with each compound.)
  • the obtained plant height inhibition rate was evaluated in five stages. As a result, a high growth control effect with an evaluation of 4 or more was observed for compounds 10, 13, 19, 26 and 33. 5: Plant height suppression rate of 50% or more 4: Plant height suppression rate of less than 50 to 30% or more 3: Plant height suppression rate of less than 30 to 20% or more 2: Plant height suppression rate of less than 20 to 10% Above 1: Plant height suppression rate is less than 10%

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Abstract

L'invention porte sur un nouveau dérivé de (méthyl hétérocyclique)azolylméthylcyclopentanol et sur un intermédiaire de celui-ci ; sur un procédé de fabrication du dérivé ; et sur une préparation pour l'agriculture ou l'horticulture et un agent protecteur pour une substance industrielle, dont chacun comprend le dérivé de (méthyl hétérocyclique)azolylméthylcyclopentanol comme ingrédient actif. De façon spécifique, l'invention porte sur un dérivé de (méthyl hétérocyclique)azolylméthylcyclopentanol représenté par la formule chimique (I). (I) dans laquelle R1 et R2 représentent indépendamment un atome d'hydrogène ou un groupe alkyle en C1-C5 ; R3 représente un groupe hétérocyclique substitué ou non substitué ou un groupe hétérocyclique condensé substitué ou non substitué ; et A représente un atome d'azote ou un groupe méthine.
PCT/JP2009/050201 2008-01-09 2009-01-09 Dérivé de (méthyl hétérocyclique)azolylméthylcyclopentanol et son intermédiaire, procédé de fabrication du dérivé et préparation pour l'agriculture ou l'horticulture et agent protecteur pour une substance industrielle comprenant chacun le dérivé Ceased WO2009088070A1 (fr)

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Cited By (7)

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WO2010122171A1 (fr) * 2009-04-24 2010-10-28 Basf Se 5-hétéroarylméthyl-i-(b-mercapto-[1,2, 4 -triazolylméthyl)-cyclopentanol servant de fongicides
WO2012169516A1 (fr) * 2011-06-07 2012-12-13 株式会社クレハ Dérivé azole, son procédé de fabrication, composé intermédiaire et agent chimique agricole ou horticole et agent de protection de matière industrielle
WO2012169559A1 (fr) * 2011-06-07 2012-12-13 株式会社クレハ Dérivé d'azole, procédé pour produire un dérivé d'azole, et composé intermédiaire
WO2013077265A1 (fr) * 2011-11-25 2013-05-30 株式会社クレハ Dérivé d'azole et son utilisation
JPWO2013157311A1 (ja) * 2012-04-18 2015-12-21 株式会社クレハ トリアゾリルメチルシクロアルカノール誘導体の製造方法、およびトリアゾリルメチルシクロアルカノール誘導体含有組成物
US9750254B2 (en) 2013-12-05 2017-09-05 Kureha Corporation Agricultural or horticultural chemical, method of controlling plant diseases, and product for controlling plant diseases
US9814236B2 (en) 2013-12-05 2017-11-14 Kureha Corporation Agricultural or horticultural chemical, method of controlling plant diseases, and product for controlling plant diseases

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WO2010122171A1 (fr) * 2009-04-24 2010-10-28 Basf Se 5-hétéroarylméthyl-i-(b-mercapto-[1,2, 4 -triazolylméthyl)-cyclopentanol servant de fongicides
US9241488B2 (en) 2011-06-07 2016-01-26 Kureha Corporation Azole derivative, method for producing azole derivative, and intermediate compound
WO2012169516A1 (fr) * 2011-06-07 2012-12-13 株式会社クレハ Dérivé azole, son procédé de fabrication, composé intermédiaire et agent chimique agricole ou horticole et agent de protection de matière industrielle
WO2012169559A1 (fr) * 2011-06-07 2012-12-13 株式会社クレハ Dérivé d'azole, procédé pour produire un dérivé d'azole, et composé intermédiaire
EA024953B1 (ru) * 2011-06-07 2016-11-30 Куреха Корпорейшн Производное азола, способ его получения, химический агент, предназначенный для применения в сельском хозяйстве и садоводстве, и агент для защиты промышленных материалов
CN103562187A (zh) * 2011-06-07 2014-02-05 株式会社吴羽 唑衍生物、其制造方法、中间体化合物、以及农业园艺用药剂及工业用材料保护剂
EP2719695A4 (fr) * 2011-06-07 2014-10-22 Kureha Corp Dérivé d'azole, procédé pour produire un dérivé d'azole, et composé intermédiaire
JPWO2012169559A1 (ja) * 2011-06-07 2015-02-23 株式会社クレハ アゾール誘導体、アゾール誘導体の製造方法、および中間体化合物
JPWO2012169516A1 (ja) * 2011-06-07 2015-02-23 株式会社クレハ アゾール誘導体、その製造方法、中間体化合物、ならびに農園芸用薬剤および工業用材料保護剤
US9440933B2 (en) 2011-06-07 2016-09-13 Kureha Corporation Azole derivative, method for producing same, intermediate compound, and agricultural or horticultural chemical agent and industrial material protecting agent
US9035069B2 (en) 2011-06-07 2015-05-19 Kureha Corporation Azole derivative, method for producing same, intermediate compound, and agricultural or horticultural chemical agent and industrial material protecting agent
CN103562187B (zh) * 2011-06-07 2015-09-09 株式会社吴羽 唑衍生物、其制造方法、中间体化合物、以及农业园艺用药剂及工业用材料保护剂
CN103946216A (zh) * 2011-11-25 2014-07-23 株式会社吴羽 唑衍生物及其应用
US9278941B2 (en) 2011-11-25 2016-03-08 Kureha Corporation Azole derivative and uses thereof
CN103946216B (zh) * 2011-11-25 2016-07-06 株式会社吴羽 唑衍生物及其应用
JPWO2013077265A1 (ja) * 2011-11-25 2015-04-27 株式会社クレハ アゾール誘導体、およびその利用
WO2013077265A1 (fr) * 2011-11-25 2013-05-30 株式会社クレハ Dérivé d'azole et son utilisation
JPWO2013157311A1 (ja) * 2012-04-18 2015-12-21 株式会社クレハ トリアゾリルメチルシクロアルカノール誘導体の製造方法、およびトリアゾリルメチルシクロアルカノール誘導体含有組成物
US9750254B2 (en) 2013-12-05 2017-09-05 Kureha Corporation Agricultural or horticultural chemical, method of controlling plant diseases, and product for controlling plant diseases
US9814236B2 (en) 2013-12-05 2017-11-14 Kureha Corporation Agricultural or horticultural chemical, method of controlling plant diseases, and product for controlling plant diseases

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