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WO1999046247A1 - Composes a base de pyrazole et produits chimiques agricoles renfermant ces composes en tant que principe actif - Google Patents

Composes a base de pyrazole et produits chimiques agricoles renfermant ces composes en tant que principe actif Download PDF

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Publication number
WO1999046247A1
WO1999046247A1 PCT/JP1999/001160 JP9901160W WO9946247A1 WO 1999046247 A1 WO1999046247 A1 WO 1999046247A1 JP 9901160 W JP9901160 W JP 9901160W WO 9946247 A1 WO9946247 A1 WO 9946247A1
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WIPO (PCT)
Prior art keywords
group
alkyl
alkoxy
hydrogen atom
alkyl group
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PCT/JP1999/001160
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English (en)
Japanese (ja)
Inventor
Hiroki Kano
Yoshiya Ikeda
Nobuo Kyomura
Hirofumi Tomita
Toshiki Fukuchi
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Mitsubishi Chemical Corporation
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Priority to AU27470/99A priority Critical patent/AU2747099A/en
Publication of WO1999046247A1 publication Critical patent/WO1999046247A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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 to ring carbon atoms
    • 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
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • 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
    • A01N55/00—Biocides, pest repellants or attractants, or plant growth regulators, containing organic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen and sulfur

Definitions

  • the present invention relates to a novel pyrazole compound, and an agricultural and horticultural drug containing the pyrazole compound as an active ingredient, particularly an insecticide, acaricide, and fungicide for agricultural and horticultural use.
  • the present invention exhibits a high control effect on various pathogens and pests that are resistant to conventional agricultural and horticultural fungicides, insecticides, and acaricides, and is an effective component of agricultural and horticultural fungicides, insecticides, and miticides
  • the purpose is to provide useful chemical substances.
  • Another object of the present invention is to provide a safe and effective agricultural and horticultural bactericidal, insecticidal, and acaricide active ingredient having the above characteristics and having reduced problems such as residual toxicity and environmental pollution.
  • the purpose is to provide useful chemical substances.
  • the present invention provides a pyrazole compound represented by the following general formula (I), and a pesticide containing this compound as an active ingredient, particularly an insecticide, acaricidal, and fungicide for agricultural and horticultural use. is there.
  • R 1 and R 2 each independently represent a hydrogen atom or an d to C 4 alkyl group
  • Y represents a group represented by the following general formula ( ⁇ ) or a group —C ⁇ C—,
  • R 7 and R 8 are each independently a hydrogen atom, an alkyl group of up to C 4 , a halogen atom, an alkoxy group of up to C 4 , an acyl group of C 2 to C 7 , up to C 7 Represents an acyloxy group.
  • R 3 is a hydrogen atom, a C, -C 6 alkyl group, a halogen atom, a -C 4 haloalkyl group, a C 2 -C 5 alkenyl group, a C 2 -C 5 alkynyl group, a C 3 -C 6 A cycloalkyl group, a hydroxyalkyl group of C, to (: 7 and a protected form thereof,
  • C 5 or C 6 hydroxycycloalkyl group (C, to (: 4 alkylthio) d to C 4 alkyl group, C, to C 7 aminoalkyl group, (C, to (: 4 alkylamino) to C 7 alkyl group, a di (C, -C 4 Arukiruamino) -C 7 alkyl group, (C 1 ⁇ (7 Ashiruamino) C, -C 7 alkyl group, Ashiru group of C 2 to c 7,
  • C, to C 4 haloalkoxy groups Fuweniru group, full enoxy group, Ashiru group of C 2 ⁇ C 7, (C, ⁇ C 4 alkoxy) carbonyl group, selected from the group consisting of an alkylthio group, and triflate Ruo b methylthio group -C 4 A phenyl group which may be substituted with a substituent
  • R 4 is a hydrogen atom, an alkyl group of C! To C 4 , an acyl group of C 2 to C 7 ,
  • R 5 and R 6 each independently represent a hydrogen atom or an alkyl group of C, to (: 4 ,
  • A represents a group represented by the following general formulas (ma) to (! ⁇ j).
  • R 9 is a hydrogen atom, (:, to ( 8 alkyl group, to C 4 alkoxy group, halogen atom, C 1 to C 4 haloalkyl group, , a haloalkoxy group ⁇ C 4, C 3 ⁇ (: 7 cycloalkoxy group, C, alkylthio group -C 5; or C, alkyl group -C 4, Aruke alkenyl group of C 2 -C 5, C alkynyl group 2 -C 5, C, alkoxy group -C 4, haloalkyl group ⁇ C 4, C, haloalkoxy groups -C 4, Nono androgenic atom, phenyl group, Fuwenokishi group, Shiano group, a nitro group, Formyl group and protected form thereof, hydroxy group, C 2 -C 7 acyl group, group represented by the following general formula (IV), (d-C 4 alkoxy) carbony
  • R ' Represents a hydrogen atom, C, alkyl or C, Haroaru kill groups -C 3 of -C 6,
  • R ′ 1 represents a hydrogen atom, an alkyl group of CC 4 or a paratoluenesulfonyl group.
  • R 12 represents a C, to C 4 alkyl group
  • R 13 represents a hydrogen atom or a C 4 alkyl group.
  • the compound of the above general formula (I) provided by the present invention has high control activity against various pathogenic bacteria and pests which are resistant to conventional fungicides, insecticides and acaricides, and is safe. It is highly useful and is extremely useful as an agricultural and horticultural drug.
  • R ′ and R 2 are each independently a hydrogen atom or C, ⁇ C such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, etc. 4 represents a linear or branched alkyl group.
  • R 1 and R 2 are preferably C, to (: 4 alkyl groups, particularly R ′ is a methyl group, and R 2 is preferably a methyl group or an ethyl group.
  • Y represents a group represented by the following general formula ( ⁇ ) or a group —C ⁇ C—.
  • R 7 and R 8 are each independently a hydrogen atom; a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-group.
  • —C 4 to C 4 straight or branched chain alkyl group such as butyl group; halogen atom such as fluorine atom, chlorine atom, bromine atom, iodine atom; methoxy group, ethoxy Alkoxy group, n- propoxy group, Isopurobokishi group, n- butoxy group, isobutoxy group, t-C or a butoxy group, an alkoxy group -C 4; Asechiru group, a propionyl group, n- Puchiriru group, Isopuchiriru group, n- C 2 -C 7 acyl groups such as valeryl group, isopallyl group, 2-methylbutyryl group, bivaloyl group, benzoyl group; etc .; C such Benzoiruokishi group, a Ashiruokishi group -C 7. ]
  • Y is preferably one C-C-.
  • R 7 and R 8 a hydrogen atom is preferable.
  • R 3 is a hydrogen atom; methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, n-hexyl, etc. d to C S straight or branched chain alkyl group; fluorine atom, chlorine atom, bromine atom, halogen atom such as iodine atom; chloromethyl group, bromomethyl group, iodomethyl group, methyl group, difluoromethyl group, trifluoromethyl group Orthomethyl group,
  • Acetal groups such as thioacetal, monothioacetyl such as 1,3-oxothiolane; trimethylsilyl group, triethylsilyl group, triisopropylsilyl group, dimethylisopropylsilyl group, dimethylisopropylsilyl group, t-butyldimethylsilyl group trialkylsilyl groups such C 3 -C 9 the like.
  • R 3 includes a phenyl group which may be substituted.
  • substituents include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group and an s-butyl group.
  • R 3 is preferably a hydrogen atom, an alkyl group of C 1 to C 6 or a hydroxyalkyl group of C 1 to CT, and more specifically, a methyl group and a hydroxymethyl group are most preferable.
  • Y is a group —C ⁇ C—
  • R 3 is most preferably a hydrogen atom.
  • R 4 is a hydrogen atom; a C, C 4 straight or branched chain such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s_butyl, t-butyl, etc.
  • Alkyl group Alkyl group; acetyl group, propionyl group, n-butyryl group, n-valeryl group, isovaleryl group, 2-methylbutyryl group, bivaloyl group, benzoyl group, and other C 2 to (: 7 acetyl group; methoxycarbonyl group) , Ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, isobutoxycarbonyl, s-butoxycarbonyl, t-butoxycarbonyl, etc.
  • R 4 is preferably a hydrogen atom or a C 2 -C, acetyl group, and more preferably, an acetyl group.
  • R 5 and R 6 are each independently a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, etc.
  • ⁇ C 4 represents a linear or branched alkyl group.
  • R 5 and R 6 are preferably a hydrogen atom or a methyl group.
  • A represents a group represented by the following general formulas (Ha) to (! ⁇ j).
  • R 9 is a hydrogen atom; methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-amyl, isoamyl, t-amyl C, ⁇ (: 8 straight or branched chain alkyl such as n-hexyl group, 1-ethyl-1-methylpropyl group, n-heptyl group, n-octyl group, 2-ethylhexyl group group; main butoxy group, Etokin group, n- propoxy group, isopropoxy opening epoxy group, n- butoxy group, isobutoxy group, s- butoxy group, t-C or a butoxy group, a -C 4 straight or branched chain alkoxy
  • a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom and an io
  • the naphthyloxy group includes a mono-naphthyloxy group or a S-naphthyloxy group.
  • Examples of the substituent of the phenoxy group or the naphthyloxy group include the following.
  • R 12 represents C, to (: 4) such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group and t-butyl group.
  • R 13 represents a hydrogen atom or a methyl, ethyl, n-propyl, isopropyl or n-butyl group.
  • group, isobutyl group, s - butyl groups, C such as t one-butyl group, a straight or branched chain alkyl group having -C 4 is a methyl group was a hydrogen atom or among these the most preferred.
  • (C, -C 4 alkoxy) carbonyl group or C, -C 4 straight chain such as methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, s-butylthio, etc. Or a branched-chain alkylthio group; or a trifluoromethylthio group.
  • the respective substituents may be the same or different.
  • the number of substitution groups is preferably one or two.
  • Examples of the substituent of the phenoxy group or the naphthyloxy group include the halogen atoms described above, d to C 4 linear or branched alkyl groups, C, to C 4 haloalkyl groups, and C, to C 4 linear or branched chains.
  • Alkylthio groups, C 2 to (: 5 alkynyl groups, oxime groups represented by the general formula (W), and C, to C 4 linear or branched alkoxy groups are preferred.
  • R 9 is preferably an optionally substituted phenoxy group or a naphthylquine group, and more preferably a substituent of the group represented by the above formula (ma-1) or (mb-1). .
  • R 9 is most preferably a phenoxy group substituted by a halogen atom.
  • R '° is a hydrogen atom; methyl, ethyl, n-propyl, isopropyl, ⁇ -butyl, isobutyl, s-butyl, a C 6 to C 6 linear or branched alkyl group such as t-butyl group, n-amyl group, isoamyl group, t-amyl group, n-hexyl group, 1-ethyl-1-methylpropyl group; fluoromethyl group , Chloromethyl, bromomethyl, difluoromethyl, dichloromethyl, dibromomethyl, trifluoromethyl, trifluoromethyl, tribromomethyl, pentafluoroethyl, heptafluoropropyl, etc.
  • C 3 represents a haloalkyl group.
  • R 11 is a hydrogen atom; methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, C of a t- butyl group and the like, -C 4 alkyl group; p-toluenesulfonyl Represents a group.
  • Groups not specifically shown in the above groups are selected in any combination from the above atoms and groups, or in accordance with generally known common sense.
  • a salt thereof is also included in the compound of the present invention.
  • the salt include commonly used agricultural and horticulturally acceptable salts known per se.
  • isomers of the compound represented by the above general formula (I) are also included in the compounds of the present invention.
  • Preferred examples of the pyrazole compound represented by the general formula (I) include a compound represented by the following general formula (I-11).
  • R 5 , R 6 and R 9 are the same as defined in the general formula (I), and W is a group CH or a nitrogen atom.
  • R 1 and R 2 are each independently an alkyl group of d to C 4 , and R 3 , R ⁇ R 5 and R 6 is a hydrogen atom at the same time, W is a group CH or a nitrogen atom, R 9 is a halogen atom, a C, -C 4 alkyl group, a C, -C 4 haloalkyl group, a C, -C 4 alkylthio group , An alkynyl group of C 2 to C 5 , an oxime group represented by the general formula (W), and a phenyl or naphthyloxy group which may be substituted with a substituent selected from the group consisting of an alkoxy group of C, to (: 4)
  • the compound is a group.
  • the compounds of the present invention represented by the general formula (I) include Hasmonyo tow, Konaga, and Tyano Lepidoptera, such as Kamakumamakimaki, Kobumemeiga, and Futaba suzuki; Dermophytes, such as Tobi-iro-jin-koku, Shiro-Gonbuka, etc., Leaf-hoppers, such as Lepidoptera, Tyanomy.
  • Hemiptera such as stink bugs such as blue stink bugs, Coleoptera, such as Lepidoptera, Chrysomelidae, Leaf beetles, and Azukizomushi; Diptera, such as house flies and Akajeka; It has a high control activity against eggs and larvae of the order Acarina, such as Citrus red mites, Citrus unicinus, and Cyanophoridae, and is therefore useful as an active ingredient for agricultural and horticultural insecticides and danicidal agents.
  • Acarina such as Citrus red mites, Citrus unicinus, and Cyanophoridae
  • the compound of the present invention has a high bactericidal effect against phytopathogenic fungi such as blast fungus, rust fungus and downy mildew fungus, and is useful as an active ingredient of a fungicide for agricultural and horticultural use.
  • insects, mites, phytopathogenic fungi and the like to be controlled by the compounds of the present invention are not limited to those exemplified above.
  • the compound of the present invention represented by the general formula (I) is used as an insecticide, acaricide, or fungicide for agricultural and horticultural use, it may be used alone, but it may be used alone. Preferably, it is in the form of a composition produced with the aid of an auxiliary.
  • emulsions wettable powders, powders, flowables, fine granules, granules, tablets, oils, sprays, aerosols, etc.
  • conventional pesticides for agricultural and horticultural use The form of the acaricide or fungicide is not limited. Further, one or more of the above compounds may be blended as an active ingredient.
  • the pesticide adjuvants used for producing the above-mentioned agricultural and horticultural insecticides, acaricides, and fungicides include, for example, improving, stabilizing, and dispersing the effects of agricultural and horticultural insecticides, acaricides, and fungicides. It can be used for the purpose of improving the properties. Specific examples include a carrier (diluent), an emulsifier, a spreading agent, a wetting agent, a dispersant, and a disintegrant.
  • liquid carrier examples include water, aromatic hydrocarbons such as toluene and xylene, alcohols such as methanol, butanol and glycol, ketones such as acetone, amides such as dimethylformamide, and sulfoxides such as dimethyl sulfoxide. , Methylnaphthalene, cyclohexane, animal and vegetable oils, fatty acids and the like.
  • Solid carriers include clay, kaolin, talc, diatomaceous earth, silica, calcium carbonate, Montmorite mouth, feldspar, quartz, alumina, sawdust, nitrocellulose, starch, gum arabic and the like can be used.
  • Usable surfactants can be used as emulsifiers and dispersants, for example, higher alcohol sodium sulfate, stearyltrimethylammonium chloride, polyoxyethylene alkylphenyl ether, lauryl betaine, etc.
  • Anionic surfactants, cationic surfactants, nonionic surfactants, amphoteric surfactants and the like can be used.
  • a spreading agent such as polyoxyethylene nonylphenyl ether and polyoxyethylene lauryl phenyl ether; a wetting agent such as dialkyl sulfosuccinate; a fixing agent such as carboxymethyl cellulose and polyvinyl alcohol; lignin sulfone Disintegrants such as sodium citrate and sodium lauryl sulfate can be used.
  • the content of the active ingredient in the agricultural and horticultural insecticide, acaricide, and fungicide of the present invention is as follows.
  • the amount is selected from the range of 0.1 to 99.5% by weight, and may be appropriately determined depending on various conditions such as the form of the preparation and the method of application. For example, about 0.5 to 20% by weight of the powder is preferable. It is preferably about 1 to 10% by weight, about 1 to 90% by weight for a wettable powder, preferably about 10 to 80% by weight, and about 1 to 90% by weight for an emulsion, preferably about 10 to 4% by weight. It is preferred to produce such that they contain 0% by weight of active ingredient.
  • an emulsion in the case of an emulsion, can be prepared by appropriately mixing a solvent, a surfactant and the like with the compound of the present invention as an active ingredient. May be applied after dilution.
  • a solvent e.g., a solvent, a surfactant and the like
  • the above compound of the active ingredient, the solid carrier, and a surfactant are mixed to produce a wettable powder, and the hydrated liquid is diluted with water to a predetermined concentration before use, and then applied. Is also good.
  • an auxiliary such as a solid carrier may be added to the above compound as an active ingredient, if necessary, and the mixture may be used as it is.
  • the granules may be produced by mixing the above-mentioned compound as an active ingredient, a solid carrier, a surfactant and the like and granulating the granules, and may be applied as it is.
  • the production method of each of the above-mentioned preparation forms is not limited to the above-mentioned one, and can be appropriately selected by those skilled in the art according to the kind of the active ingredient, the purpose of application, and the like.
  • the agricultural and horticultural insecticides, acaricides, and fungicides of the present invention include, in addition to the compound of the present invention, an active ingredient, other fungicides, insecticides, acaricides, herbicides, and insect growth regulators. Any active ingredient such as fertilizer, soil conditioner, etc. may be added.
  • the method for applying the fungicide for agricultural and horticultural use, the insecticide and the acaricide of the present invention is not particularly limited, and it may be applied by any method such as foliage application, water application, soil treatment, seed treatment, and soil admixture treatment. You can do this.
  • a solution having a concentration range of 5 to 100 ppm, preferably 10 to 500 ppm is applied at a rate of about 100 to 200 liters per 10 ares. It can be used in dosages.
  • the application rate is usually 1 to 10 kg per 10 ares for granules with 5 to 15% of active ingredient.
  • soil treatment it can be used in. 5 to 1 0 0 0 p pm concentration range of the solution to 1 m 2 per 1 to 1 0 rates Torr about facilities doses.
  • a solution in a concentration range of 10 to 100 ppm per 1 kg of seed weight can be applied to the solution in an amount of about 10 to 100 milliliters.
  • the compound of the present invention represented by the general formula (I) can be produced, for example, according to the following reaction formula.
  • R ′, R 2 , R 3 , R 4 , R 5 , R 6 , Y and A are as defined in the general formula (I), and Q is a halogen atom such as a chlorine atom, a bromine atom, etc.
  • Q is a halogen atom such as a chlorine atom, a bromine atom, etc.
  • the solvent may be used in a solvent-free state or in a high boiling point solvent such as N, N-dimethylformamide, N-methylpyrrolidone or dimethylsulfoxide.
  • the compound of the general formula (VI) can be obtained by reacting the compound of the general formula (VI) with the compound preferably at 200 to 250.
  • Q is a hydroxyl group in the general formula (V)
  • Compounds represented by the general formula (VI) include dicyclohexylcarbodiimide (DCC), diisopropylpropylcarbodiimide (DIPC), N-ethyl-N'-3-dimethylaminopropylcarbodiimide (WS CI), benzotriazo-l-l-lu-tris (dimethylamino) phosphoniumhexafluorophosphoride (BOT), diphenylphosphoryl azide (DPPA), etc.
  • DCC dicyclohexylcarbodiimide
  • DIPC diisopropylpropylcarbodiimide
  • WS CI N-ethyl-N'-3-dimethylaminopropylcarbodiimide
  • BOT diphenylphosphoryl azide
  • DPPA diphenylphosphoryl azide
  • the compound represented by the general formula (V) is represented by the method described in, for example, Anna 1 ender Chemie, Justus Liebig's, 536, 97 (1938), and represented by the general formula (VI). Such a compound can be produced, for example, according to the method described in Journa 1 fur Practician Chemie, 146, 95 (1936). Further, when Y is a group —c ⁇ c—, it can be produced, for example, according to the following reaction formula.
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and A are as defined in the general formula (I).
  • a compound of the general formula (W) in which X is a halogen such as a chlorine atom, a bromine atom or an iodine atom is synthesized according to a known synthesis method as described above, and an aromatic solvent such as benzene, toluene or xylene is used as a solvent.
  • Hydrocarbons such as chloroform and methylene chloride; water; esters such as methyl acetate and ethyl acetate; tetrahydrofuran, 1,2-dimethoxetane, acetonitrile, dioxane, N, N-dimethylformamid Or a polar solvent such as N-methylpyrrolidone or dimethylsulfoxide, or a mixed solvent thereof in the presence of an amine such as getylamine, butylamine, and triethylamine, or a base of an inorganic salt such as carbonate lime. Or 0-150 in amines such as getylamine, triethylamine, etc.
  • the compound (M) and the terminal acetylene compound ( ⁇ ) are combined with 0.1 to 10 Omo 1%, preferably 1 to 2 Omo 1% tetraxtriphenylphenylphosphine palladium.
  • the compound of the formula (I-a) can also be produced by the reaction using (1) and the like.
  • R ′, R 2 , R 3 , R 4 , R 5 , R 6 and A are as defined in the general formula (I).
  • a compound represented by the general formula (Ia) synthesized according to a known synthesis method is used, and a solvent is a hydrocarbon such as hexane, heptane or cyclohexane; or an aromatic such as benzene, toluene or xylene.
  • a solvent is a hydrocarbon such as hexane, heptane or cyclohexane; or an aromatic such as benzene, toluene or xylene.
  • the precipitated salts were filtered, the filtrate was concentrated, ethyl acetate was added, and the organic layer was washed with 1N hydrochloric acid, water, saturated aqueous sodium hydrogen carbonate, and saturated saline in this order, dried over anhydrous sodium sulfate, filtered, and the solvent was removed. Was distilled off to obtain a crude product.
  • mp 115-116 ° C or less
  • formulations of the insecticide, acaricide, and fungicide for agricultural and horticultural use containing the compound of the present invention as an active ingredient containing the compound of the present invention as an active ingredient.
  • the forms of acaricides and fungicides are not limited to those described below.
  • Example 1 Cabbage cut leaves (diameter 6 cm) were immersed in a water dilution of the insecticide (wettable powder) of the present invention manufactured according to the formulation of Example 1 for 1 minute. After immersion, it was air-dried and placed in a plastic cup (7 cm in inside diameter). Five third-instar larvae of the Japanese moth were released into this cup (1 concentration, 2 repetitions). After 4 days from the release, the larvae were examined for life and death and agony, and the killing rate (%) was calculated with 1/2 of the agony insects killed. Table 13 shows the results.
  • Table 1 3 Insecticidal effect on the larvae of the diamondback moth
  • Test Example 1 Acaricidal effect on adult adults
  • Preparation Example 1 A solution (3.5 mL) prepared by diluting the acaricide of the present invention (water dispersible powder) prepared according to the prescription of 1 to a predetermined concentration with water was placed on the above-mentioned cut leaves by a rotary spraying tower ( (Mizuho Rika) (1 concentration, 2 replicates). Twenty-four hours after treatment, adult mortality was examined and the kill rate (%) was determined. Table 14 shows the results.
  • Test Example 1 4 Acaricidal effect on the eggs of Nami-nada
  • Formulation Example 11 A solution (3.5 mL) prepared by diluting the acaricide (wetting agent) of the present invention to a predetermined concentration with water, prepared according to the formulation of Example 1, was spread on the above-mentioned disk by a rotary sprayer ( (Mizuho Rika)
  • Formulation of a wettable powder prepared in the same manner as in Example 1 was diluted to a prescribed concentration in 1-2-wheat wheat (cultivar: Norin 61) grown in pots with a diameter of 6 cm. Foliage was sprayed at a ratio of Om1. After air-drying with chemicals, spraying and spraying a spore suspension obtained by grinding wheat leaves infected with wheat leaf rust (Pucciniarecondita), keeping in a moist chamber at 22 ° C for 24 hours, and then in a greenhouse To? Left for ⁇ 10 days. For evaluation, the diseased area ratio of each leaf was evaluated, and the control value was calculated in the same manner as in Test Example 1. The results are shown in Table-6.
  • Tomatoes of 3 to 5 leaf stage (variety: Red Cherry) grown in pots with a diameter of 9 cm, a dilution of the prescribed concentration prepared in the same manner as in Formulation Example 1 at a ratio of 10 ml / bottom With foliage.
  • spray inoculation with a zoospore sac suspension obtained from tomato leaves infected with Phy tophthorainfestans keeping in a moist chamber at 22 ° C for 24 hours, and then in a greenhouse
  • the diseased area ratio of each leaf was evaluated, and the control value was calculated in the same manner as in Test Example 1. Table 7 shows the results.
  • novel pyrazole compound of the present invention has an extremely excellent controlling effect on various plant pathogenic bacteria, pests, etc., and is particularly useful as an agricultural and horticultural insecticide, acaricide, and fungicide. .

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne des composés à base de pyrazole, utiles comme insecticide, acaricide et bactéricide, représentés par la formule générale I. Les produits chimiques renfermant ces composés, en tant que principe actif, sont utilisés dans l'agriculture et l'horticulture, comme insecticide, acaricide et bactéricide. Dans ladite formule, R1 et R2 sont chacun hydrogène ou alkyle; Y est un groupe comportant ⊃C=C∫ ou un groupe représenté par -C C-; R3 est hydrogène ou un substituant, par exemple alkyle ou halogéno; R4 est hydrogène ou un substituant, par exemple alkyle ou acyle; R5 et R6 sont chacun hydrogène ou alkyle; et A est phényle ou un groupe hétérocyclique à cinq ou six éléments.
PCT/JP1999/001160 1998-03-11 1999-03-10 Composes a base de pyrazole et produits chimiques agricoles renfermant ces composes en tant que principe actif WO1999046247A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU27470/99A AU2747099A (en) 1998-03-11 1999-03-10 Pyrazole compounds and agricultural chemicals containing the same as active ingredient

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP5951098A JP2002187882A (ja) 1998-03-11 1998-03-11 ピラゾール化合物およびこれを有効成分とする農薬
JP10/59510 1998-03-11

Publications (1)

Publication Number Publication Date
WO1999046247A1 true WO1999046247A1 (fr) 1999-09-16

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1999/001160 WO1999046247A1 (fr) 1998-03-11 1999-03-10 Composes a base de pyrazole et produits chimiques agricoles renfermant ces composes en tant que principe actif

Country Status (3)

Country Link
JP (1) JP2002187882A (fr)
AU (1) AU2747099A (fr)
WO (1) WO1999046247A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003062222A1 (fr) * 2002-01-21 2003-07-31 Nihon Nohyaku Co., Ltd. Carboxamides de pyrazole, intermediaires associes et pesticides contenant ces derniers en tant qu'ingredient actif
WO2004026839A1 (fr) * 2002-09-19 2004-04-01 Agro-Kanesho Co.,Ltd. Procede pour produire un compose d'arylethynylpyrazole
CN1325427C (zh) * 2000-03-13 2007-07-11 陶氏环球技术公司 改良混凝土及其制备方法
CN115925681A (zh) * 2022-04-22 2023-04-07 中国农业大学 一类吡唑酰胺类化合物、其制备及作为杀虫剂和杀菌剂的应用

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH697574B1 (de) * 2003-01-07 2008-12-15 Lanxess Deutschland Gmbh Pyrazolylarylalkine.
CN101175750B (zh) * 2005-05-13 2011-09-07 拜尔农科股份公司 杀真菌剂2-吡啶基-亚甲基-羧酰胺衍生物

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0363262A (ja) * 1989-08-01 1991-03-19 Sumitomo Chem Co Ltd ブロモジフルオロメトキシベンゼン系化合物およびそれを有効成分とする殺虫、殺ダニ剤
JPH0632781A (ja) * 1992-05-13 1994-02-08 Sandoz Ag 新規ピラゾール類
JPH09278775A (ja) * 1996-04-05 1997-10-28 Mitsubishi Chem Corp ピラゾール化合物及びこれを有効成分とする殺虫、殺ダニ、殺菌剤

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0363262A (ja) * 1989-08-01 1991-03-19 Sumitomo Chem Co Ltd ブロモジフルオロメトキシベンゼン系化合物およびそれを有効成分とする殺虫、殺ダニ剤
JPH0632781A (ja) * 1992-05-13 1994-02-08 Sandoz Ag 新規ピラゾール類
JPH09278775A (ja) * 1996-04-05 1997-10-28 Mitsubishi Chem Corp ピラゾール化合物及びこれを有効成分とする殺虫、殺ダニ、殺菌剤

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1325427C (zh) * 2000-03-13 2007-07-11 陶氏环球技术公司 改良混凝土及其制备方法
WO2003062222A1 (fr) * 2002-01-21 2003-07-31 Nihon Nohyaku Co., Ltd. Carboxamides de pyrazole, intermediaires associes et pesticides contenant ces derniers en tant qu'ingredient actif
WO2004026839A1 (fr) * 2002-09-19 2004-04-01 Agro-Kanesho Co.,Ltd. Procede pour produire un compose d'arylethynylpyrazole
CN115925681A (zh) * 2022-04-22 2023-04-07 中国农业大学 一类吡唑酰胺类化合物、其制备及作为杀虫剂和杀菌剂的应用

Also Published As

Publication number Publication date
JP2002187882A (ja) 2002-07-05
AU2747099A (en) 1999-09-27

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