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WO2019009387A1 - Procédé de production d'un composé heterocyclique condensé - Google Patents

Procédé de production d'un composé heterocyclique condensé Download PDF

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Publication number
WO2019009387A1
WO2019009387A1 PCT/JP2018/025615 JP2018025615W WO2019009387A1 WO 2019009387 A1 WO2019009387 A1 WO 2019009387A1 JP 2018025615 W JP2018025615 W JP 2018025615W WO 2019009387 A1 WO2019009387 A1 WO 2019009387A1
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group
halo
general formula
compound represented
alkoxy
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PCT/JP2018/025615
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English (en)
Japanese (ja)
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登 阿部
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日本農薬株式会社
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Publication of WO2019009387A1 publication Critical patent/WO2019009387A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles

Definitions

  • the present invention relates to a process for producing fused heterocyclic compounds useful as insecticides.
  • the fused heterocyclic compound of the present invention is useful as an insecticide, particularly as an agricultural and horticultural insecticide and an animal ectoparasite control agent.
  • a method of performing a cyclization reaction after forming an amide bond which is disclosed in Patent Document 1, etc., is reported.
  • any of the methods as to the method via the CH bond activated transition metal catalyzed cross coupling reaction of a substituted benzoxazole according to the present invention with a 2-position halogen substituted pyridine derivative, There is no disclosure or suggestion.
  • the object of the present invention is to provide a novel and industrially advantageous process for producing fused heterocyclic compounds useful as insecticides.
  • the present inventors have found that cross coupling reactions of substituted benzoxazoles and 2-position halogen substituted pyridine derivatives in the presence of a CH bond activated transition metal catalyst and subsequent reactions
  • the present inventors have completed the present invention by finding a short-step and high-yield production method of a fused heterocyclic compound useful as an insecticide by the reaction. It is industrially advantageous without requiring complicated process control.
  • R 1 is (a1) hydrogen atom; (a2) halogen atom; (a3) (C 1 -C 6 ) alkyl group; (a4) halo (C 1 -C 6 ) alkyl group; (a5) (C 1 -C 6 ) alkoxy group; (a6) halo (C 1 -C 6 ) alkoxy; (a7) halo (C 1 -C 6 ) alkylthio group; (a8) halo (C 1 -C 6 ) alkylsulfinyl group; or (a9) A halo (C 1 -C 6 ) alkylsulfonyl group is shown.
  • R 2 is (b1) hydrogen atom; (b2) halogen atom; (b3) (C 1 -C 6 ) alkyl group; (b4) (C 3 -C 6 ) cycloalkyl group; (b5) (C 1 -C 6 ) alkoxy group; (b6) halo (C 1 -C 6 ) alkyl groups; (b7) halo (C 3 -C 6 ) cycloalkyl group; (b8) halo (C 1 -C 6 ) alkoxy; (b9) halo (C 1 -C 6 ) alkylthio group; (b10) halo (C 1 -C 6 ) alkylsulfinyl group; or (b11) a halo (C 1 -C 6 ) alkylsulfonyl group is shown.
  • n an integer of 1 or 2.
  • R 1 is (a1) hydrogen atom; (a2) halogen atom; (a3) (C 1 -C 6 ) alkyl group; (a4) halo (C 1 -C 6 ) alkyl group; (a5) (C 1 -C 6 ) alkoxy group; (a6) halo (C 1 -C 6 ) alkoxy; (a7) halo (C 1 -C 6 ) alkylthio group; (a8) halo (C 1 -C 6 ) alkylsulfiny
  • R 2 is (b1) hydrogen atom; (b2) halogen atom; (b3) (C 1 -C 6 ) alkyl group; (b4) (C 3 -C 6 ) cycloalkyl group; (b5) (C 1 -C 6 ) alkoxy group; (b6) halo (C 1 -C 6 ) alkyl groups; (b7) halo (C 3 -C 6 ) cycloalkyl group; (b8) halo (C 1 -C 6 ) alkoxy; (b9) halo (C 1 -C 6 ) alkylthio group; (b10) halo (C 1 -C 6 ) alkylsulfinyl group; or (b11) a halo (C 1 -C 6 ) alkylsulfonyl group is shown.
  • n an integer of 1 or 2.
  • R 1 is (a1) hydrogen atom; (a2) halogen atom; (a3) (C 1 -C 6 ) alkyl group; (a4) halo (C 1 -C 6 ) alkyl group; (a5) (C 1 -C 6 ) alkoxy group; (a6) halo (C 1 -C 6 ) alkoxy; (a7) halo (C 1 -C 6 ) alkylthio group; (a8) halo (C 1 -C 6 ) alkylsulfinyl group; or (a9) A halo (C 1 -C 6 ) alkylsulfonyl group is shown.
  • R 2 is (b1) hydrogen atom; (b2) halogen atom; (b3) (C 1 -C 6 ) alkyl group; (b4) (C 3 -C 6 ) cycloalkyl group; (b5) (C 1 -C 6 ) alkoxy group; (b6) halo (C 1 -C 6 ) alkyl groups; (b7) halo (C 3 -C 6 ) cycloalkyl group; (b8) halo (C 1 -C 6 ) alkoxy; (b9) halo (C 1 -C 6 ) alkylthio group; (b10) halo (C 1 -C 6 ) alkylsulfinyl group; or (b11) a halo (C 1 -C 6 ) alkylsulfonyl group is shown.
  • n an integer of 1 or 2.
  • a method of producing a compound represented by General formula (2) (Wherein, R 1 and R 2 are as defined above, and Y is a halogen atom; or (C 1 -C 6 ) alkylsulfonyl group).
  • R 1 is (a1) hydrogen atom; (a2) halogen atom; (a3) (C 1 -C 6 ) alkyl group; (a4) halo (C 1 -C 6 ) alkyl group; (a5) (C 1 -C 6 ) alkoxy group; (a6) halo (C 1 -C 6 ) alkoxy; (a7) halo (C 1 -C 6 ) alkylthio group; (a8) halo (C 1 -C 6 ) alkylsulfinyl group; or (a9) A halo (C 1 -C 6 ) alkylsulfonyl group is shown.
  • R 2 is (b1) hydrogen atom; (b2) halogen atom; (b3) (C 1 -C 6 ) alkyl group; (b4) (C 3 -C 6 ) cycloalkyl group; (b5) (C 1 -C 6 ) alkoxy group; (b6) halo (C 1 -C 6 ) alkyl groups; (b7) halo (C 3 -C 6 ) cycloalkyl group; (b8) halo (C 1 -C 6 ) alkoxy; (b9) halo (C 1 -C 6 ) alkylthio group; (b10) halo (C 1 -C 6 ) alkylsulfinyl group; or (b11) a halo (C 1 -C 6 ) alkylsulfonyl group is shown.
  • n an integer of 1 or 2.
  • a method of producing a compound represented by General formula (1-1) (Wherein, R 1 and R 2 are as defined above) A process of performing an oxidation reaction on the compound represented by [5] A reaction between the compound represented by the general formula (4) and the compound represented by the general formula (3), characterized in that the reaction is performed in the presence of a transition metal catalyst,
  • R 1 is (a2) halogen atom; (a4) halo (C 1 -C 6 ) alkyl group; (a6) halo (C 1 -C 6 ) alkoxy; (a7) halo (C 1 -C 6 ) alkylthio group; (a8) halo (C 1 -C 6 ) alkylsulfinyl group; or (a9) halo (C 1 -C 6 ) alkylsulfonyl group, The manufacturing method according to any one of the above [1] to [5
  • R 2 is (b1) hydrogen atom; (b2) halogen atom; (b3) (C 1 -C 6 ) alkyl group; (b4) (C 3 -C 6 ) cycloalkyl group; (b5) (C 1 -C 6 ) alkoxy group; (b6) halo (C 1 -C 6 ) alkyl groups; (b7) halo (C 3 -C 6 ) cycloalkyl group; (b8) halo (C 1 -C 6 ) alkoxy; (b9) halo (C 1 -C 6 ) alkylthio group; (b10) halo (C 1 -C 6 ) alkylsulfinyl group; or (b11) represents a halo (C 1 -C 6 ) alkylsulfonyl group; X represents a halogen atom, Y represents a halogen atom; or (C 1
  • the target compound can be produced efficiently and economically advantageously on an industrial scale.
  • Halo means "halogen atom” and represents a chlorine atom, a bromine atom, an iodine atom or a fluorine atom.
  • the "(C 1 -C 6 ) alkyl group” is, for example, methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, isobutyl group, secondary butyl group, tertiary butyl group, normal pentyl group, isopentyl group Tertiary pentyl group, neopentyl group, 2,3-dimethylpropyl group, 1-ethylpropyl group, 1-methylbutyl group, 2-methylbutyl group, normal hexyl group, isohexyl group, 2-hexyl group, 3-hexyl group, Indicates a linear or branched alkyl group having 1 to 6 carbon atoms, such as 2-methylp
  • the “(C 3 -C 6 ) cycloalkyl group” is a cyclic alkyl group having 3 to 6 carbon atoms, such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, etc., and “(C 1 ⁇ As C 6 ) alkoxy group ”, for example, methoxy group, ethoxy group, normal propoxy group, isopropoxy group, normal butoxy group, secondary butoxy group, tertiary butoxy group, normal pentyloxy group, isopentyloxy group, tertiary Pentyloxy group, neopentyloxy group, 2,3-dimethylpropyloxy group, 1-ethylpropyloxy group, 1-methylbutyloxy group, normal hexyloxy group, isohexyloxy group, 1,1,2-trimethylpropyl group A linear or branched chain having 1 to 6 carbon atoms, such as an
  • Examples of “(C 1 -C 6 ) alkylthio group” include methylthio group, ethylthio group, normal propylthio group, isopropylthio group, normal butylthio group, secondary butylthio group, tertiary butylthio group, normal pentylthio group.
  • Examples of “(C 1 -C 6 ) alkylsulfinyl group” include methylsulfinyl group, ethylsulfinyl group, normal propylsulfinyl group, isopropylsulfinyl group, normal butylsulfinyl group, secondary butylsulfinyl group, tertiary butylsulfinyl group, Normal pentyl sulfinyl group, isopentyl sulfinyl group, tertiary pentyl sulfinyl group, neopentyl sulfinyl group, 2,3-dimethylpropyl sulfinyl group, 1-ethylpropylsulfinyl group, 1-methylbutylsulfinyl group, normal hexylsulfinyl group, iso Indicates a linear or branched C 1-6 alkyls
  • Examples of the “(C 1 -C 6 ) alkylsulfonyl group” include a methylsulfonyl group, an ethylsulfonyl group, a normal propylsulfonyl group, an isopropylsulfonyl group, a normal butylsulfonyl group, a secondary butylsulfonyl group, and a tertiary butylsulfonyl group, Normal pentyl sulfonyl group, isopentyl sulfonyl group, tertiary pentyl sulfonyl group, neopentyl sulfonyl group, 2,3-dimethylpropyl sulfonyl group, 1-ethylpropyl sulfonyl group, 1-methyl butyl sulfonyl group, normal hexyl sulfonyl group, iso
  • halogen atoms may be substituted at substitutable positions of “(C 1 -C 6 ) alkylsulfonyl group” and “(C 3 -C 6 ) cycloalkyl group”, and halogens are substituted When the number of atoms is 2 or more, the halogen atoms may be the same or different.
  • Halo (C 1 -C 6 ) alkyl group “halo (C 1 -C 6 ) alkoxy group”, “halo (C 1 -C 6 ) alkylthio group”, “halo (C 1 -C 6 )” respectively It is referred to as “alkylsulfinyl group”, “halo (C 1 -C 6 ) alkylsulfonyl group”, and “halo (C 3 -C 6 ) cycloalkyl group”.
  • (C 1 -C 6 ) “(C 1 -C 3 )” and the like indicate the range of carbon atoms in various substituents, and in the case of “(C 1 -C 6 ) alkyl group”, for example Represents a linear or branched alkyl group having 1 to 6 carbon atoms, and in the case of “(C 1 -C 3 ) alkyl group”, a linear or branched alkyl group having 1 to 3 carbon atoms Indicates
  • the compounds represented by the general formulas (1), (1-1), (2) and (3) (4) included in the production method of the present invention have one or more asymmetric groups in their structural formulae. There may be a center, and there may be two or more optical isomers and diastereomers, and the production method of the present invention includes all of each optical isomer and a mixture containing them in any ratio. It is
  • R 1 is (a2) halogen atom; (a4) halo (C 1 -C 6 ) alkyl group; (a6) halo (C 1 -C 6 ) alkoxy; (a7) halo (C 1 -C 6 ) alkylthio group; (a8) halo (C 1 -C 6 ) alkylsulfinyl group; or (a9) halo (C 1 -C 6 ) alkylsulfonyl group, More preferably, (a2) halogen atom; (a4) halo (C 1 -C 6 ) alkyl group; (a7) halo (C 1 -C 6 ) alkylthio group; (a8) halo (C 1 -C 6 ) alkylsulfinyl group; or (a9) A halo (C 1 -C 6 ) alkylsulfonyl group.
  • R 2 is (b2) halogen atom; (b3) (C 1 -C 6 ) alkyl group; (b4) (C 3 -C 6 ) cycloalkyl group; (b6) halo (C 1 -C 6 ) alkyl groups; (b8) halo (C 1 -C 6 ) alkoxy group; or (b9) a halo (C 1 -C 6 ) alkylthio group, More preferably, (b4) (C 3 -C 6 ) cycloalkyl group.
  • the compound represented by General formula (1) can be manufactured by the manufacturing method of following process [a] thru
  • Process [a] The process of manufacturing the compound represented by General formula (2) by making the compound represented by General formula (4), and the compound represented by General formula (3) react.
  • Step [b] A step of producing a compound represented by the general formula (1-1) by reacting the compound represented by the general formula (2) with ethanethiol or a salt thereof and the like.
  • Step [c] A step of producing a compound represented by the general formula (1) by oxidizing the compound represented by the general formula (1-1).
  • the compound represented by the general formula (2) is generally a compound represented by the general formula (4) and a compound represented by the general formula (3), a transition metal catalyst and It can be produced by reacting in an inert solvent in the presence of a base. This reaction may be carried out according to known methods or methods known per se.
  • palladium compounds such as available zero-valent or divalent palladium metals and salts (including complexes) thereof can be used, and may be supported on activated carbon or the like .
  • palladium (0) / carbon palladium (II) acetate, palladium (II) trifluoroacetate, palladium (II) chloride, bis (triphenyl phosphine) palladium (II) chloride, tetrakis (triphenyl phosphine) palladium ( 0), [1,1′-bis (diphenylphosphino) ferrocene] palladium dichloride, [1,1′-bis (diphenylphosphino) propane] palladium dichloride, [1,1′-bis (diphenylphosphino) butane] ] Palladiumdichloride, bis (dibenzylideneacetone) palladium, tris (dibenzylideneacetone) palladium, tri
  • phosphine ligands examples include triphenylphosphine (PPh 3 ), methyl diphenylphosphine (Ph 2 PCH 3 ), triflyl phosphine (P (2-furyl) 3 ), and triphenylphosphine (P (2-furyl) 3 ).
  • the amount of the ligand used may be appropriately selected usually from the range of 0.001 mol% to 20 mol% with respect to the compound represented by the general formula (4).
  • hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide
  • lithium carbonate lithium hydrogen carbonate, sodium hydrogen carbonate, sodium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, potassium hydrogen carbonate
  • Carbonates such as cesium, acetates such as lithium acetate, sodium acetate and potassium acetate, phosphates such as trisodium phosphate and tripotassium phosphate, sodium methoxide, sodium ethoxide, lithium tertiary butoxide, sodium tartha Metal oxides such as leavetoxide and potassium tert-butoxide, metal hydrides such as sodium hydride and potassium hydride, pyridine, picoline, lutidine, triethylamine, tributylamine, diisopropylethylamine, N, N-dicyclo And organic bases such as cyclohexyl methyl amine.
  • Preferred bases are, for example, sodium carbonate, sodium hydrogen carbonate, potassium carbonate, sodium acetate, potassium acetate.
  • the amount of the base used may be appropriately selected usually in the range of 1 mol to 10 mol with respect to 1 mol of the compound represented by the general formula (4).
  • any solvent which does not significantly inhibit this reaction may be used.
  • linear or cyclic ethers such as diethyl ether, tetrahydrofuran (THF), dioxane, etc., benzene, toluene, xylene, etc.
  • Aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, nitriles such as acetonitrile, esters such as ethyl acetate, N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, Polar solvents such as 1,3-dimethyl-2-imidazolidinone, alcohols such as methanol, ethanol and isopropanol, water and the like can be mentioned, with preference given to toluene, N, N-dimethylformamide, N, N- It is dimethylacetamide.
  • These inert solvents may be used alone or in combination of two or more. The amount thereof to be used may be appropriately selected usually in the range of 0.1 to 100 L with respect to 1 mole of the compound represented by the general formula (4).
  • reaction temperature is usually in the range of about 0 ° C. to 200 ° C.
  • reaction time varies depending on the reaction scale, reaction temperature and the like, and is not constant, but may be appropriately selected in the range of several minutes to 48 hours.
  • the desired product may be isolated from the reaction system containing the desired product by a conventional method, and the desired product can be produced by purification by recrystallization, column chromatography, etc., as necessary. It can also be used for the next reaction without isolation.
  • the compound represented by the general formula (1-1) is represented by the compound represented by the general formula (2) in the presence of a base and an inert solvent and represented by the formula (1-2) Can be produced by reacting ethanethiol or a salt thereof.
  • hydroxides such as lithium hydroxide, sodium hydroxide and potassium hydroxide
  • lithium carbonate lithium hydrogen carbonate, sodium hydrogen carbonate, sodium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, potassium hydrogen carbonate
  • Carbonates such as cesium, acetates such as lithium acetate, sodium acetate and potassium acetate, phosphates such as trisodium phosphate and tripotassium phosphate, sodium methoxide, sodium ethoxide, lithium tertiary butoxide, sodium tartha Metal oxides such as leavetoxide and potassium tert-butoxide, metal hydrides such as sodium hydride and potassium hydride, pyridine, picoline, lutidine, triethylamine, tributylamine, diisopropylethylamine, N, N-dicyclo And organic bases such as cyclohexyl methyl amine.
  • One or more species may be used. Preferred are lithium hydroxide, sodium hydroxide and potassium hydroxide.
  • the amount of the base used may be appropriately selected usually in the range of 1-fold mol to 10-fold mol with respect to 1 mol of the compound represented by the general formula (2).
  • tetra-n-butyl ammonium chloride tetra-n-butyl ammonium bromide, tetra-n-butyl ammonium iodide, tetra-n-octyl ammonium chloride, tetra-n-octyl ammonium bromide, Tetra-n-octyl ammonium iodide and the like
  • the amount thereof to be used may be appropriately selected usually from the range of 0.01 mol to 1 mol with respect to 1 mol of the compound represented by the general formula (2).
  • any solvent which does not significantly inhibit this reaction may be used.
  • linear or cyclic ethers such as diethyl ether, tetrahydrofuran (THF), dioxane, etc., benzene, toluene, xylene, etc.
  • Aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, nitriles such as acetonitrile, esters such as ethyl acetate, N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, Polar solvents such as 1,3-dimethyl-2-imidazolidinone, alcohols such as methanol, ethanol and isopropanol, water, etc. may be mentioned, and these inert solvents may be used alone or in combination of two or more. You can also The amount thereof to be used may be appropriately selected usually in the range of 0.1 to 100 L per 1 mol of the compound represented by the general formula (2).
  • reaction temperature is usually in the range of about 0 ° C. to 200 ° C.
  • reaction time varies depending on the reaction scale, reaction temperature and the like, and is not constant, but may be appropriately selected in the range of several minutes to 48 hours.
  • the desired product may be isolated from the reaction system containing the desired product by a conventional method, and the desired product can be produced by purification by recrystallization, column chromatography, etc., as necessary. It can also be used for the next reaction without isolation.
  • the compound represented by the general formula (1) can be produced by reacting the compound represented by the general formula (1-1) with an oxidizing agent in an inert solvent .
  • peroxides such as a hydrogen-peroxide solution, a perbenzoic acid, m-chloro perbenzoic acid, etc. are mentioned, for example.
  • oxidizing agents can be appropriately selected usually in the range of 1-fold mol to 5-fold mol with respect to the compound represented by General Formula (1-1).
  • any solvent which does not significantly inhibit this reaction may be used.
  • linear or cyclic ethers such as diethyl ether, tetrahydrofuran and dioxane, aromatic carbonization such as benzene, toluene and xylene Hydrogens, halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride, halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene, nitriles such as acetonitrile, esters such as ethyl acetate, formic acid, acetic acid and the like
  • polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, 1,3-dimethyl-2-imidazolidinone and water, and these inert solvents may be used alone or in combination. Two or more types can be mixed and used. The amount thereof to be used may be appropriately selected
  • the reaction temperature in this reaction may be appropriately selected usually in the range of ⁇ 10 ° C. to the reflux temperature of the inert solvent used.
  • the reaction time varies depending on the reaction scale, reaction temperature and the like, and although not constant, it may be appropriately selected usually in the range of several minutes to 48 hours.
  • the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography, etc., as necessary.
  • compound (1), compound (1-1), compound (2), compound (3) and compound (4) involved in the present invention include the case where a salt is formed.
  • salts include salts with inorganic acids such as hydrochloric acid, sulfuric acid and phosphoric acid, for example, salts with organic acids such as oxalic acid, acetic acid and succinic acid, salts with inorganic bases such as sodium and calcium, For example, salts with organic bases such as trimethylamine and triethylamine can be exemplified.
  • inorganic acids such as hydrochloric acid, sulfuric acid and phosphoric acid
  • organic acids such as oxalic acid, acetic acid and succinic acid
  • salts with inorganic bases such as sodium and calcium
  • salts with organic bases such as trimethylamine and triethylamine
  • the method for producing a fused heterocyclic compound according to the present invention can provide a fused heterocyclic compound in a short step and in a high yield, so the production method is industrially useful.

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  • Plural Heterocyclic Compounds (AREA)
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Abstract

Selon l'invention, le composé représenté par la formule générale (1) (dans laquelle R1 et R2 représentent un groupe halogéno (C1-C6) alkyle ou un groupe halogéno (C1-C6) alkylthio) est utile en tant que pesticide agricole, et il existe une forte demande portant sur le développement d'un procédé industriellement avantageux de synthèse dudit composé dans un procédé court. L'invention concerne un procédé de production du composé représenté par la formule générale (1), le procédé comprenant une étape de production d'un composé représenté par la formule générale (2) à l'aide d'une réaction de couplage d'un composé représenté par la formule générale (4) (dans laquelle R1 est tel que défini précédemment) et d'un composé représenté par la formule générale (3) (dans laquelle R2 est tel que défini précédemment, X représente un atome d'halogène, et Y représente un atome d'halogène ou un groupe halogéno (C1-C6) alkylthio).
PCT/JP2018/025615 2017-07-07 2018-07-06 Procédé de production d'un composé heterocyclique condensé WO2019009387A1 (fr)

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Cited By (2)

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Publication number Priority date Publication date Assignee Title
WO2024085224A1 (fr) * 2022-10-20 2024-04-25 住友化学株式会社 Cristal de 2-(5-cyclopropyl-3-(éthylsulfonyl)pyridin-2-yl)-5-((trifluorométhyl)sulfonyl)benzo[d]oxazole
WO2024085225A1 (fr) * 2022-10-20 2024-04-25 住友化学株式会社 Cristal de 2-(5-cyclopropyl-3-(éthylsulfonyl)pyridin-2-yl)-5-((trifluorométhyl)sulfinyl)benzo[d]oxazole

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024085224A1 (fr) * 2022-10-20 2024-04-25 住友化学株式会社 Cristal de 2-(5-cyclopropyl-3-(éthylsulfonyl)pyridin-2-yl)-5-((trifluorométhyl)sulfonyl)benzo[d]oxazole
WO2024085225A1 (fr) * 2022-10-20 2024-04-25 住友化学株式会社 Cristal de 2-(5-cyclopropyl-3-(éthylsulfonyl)pyridin-2-yl)-5-((trifluorométhyl)sulfinyl)benzo[d]oxazole
JP7489565B1 (ja) 2022-10-20 2024-05-23 住友化学株式会社 ２－（５－シクロプロピル－３－（エチルスルホニル）ピリジン－２－イル）－５－（（トリフルオロメチル）スルホニル）ベンゾ［ｄ］オキサゾールの結晶
JP7489564B1 (ja) 2022-10-20 2024-05-23 住友化学株式会社 ２－（５－シクロプロピル－３－（エチルスルホニル）ピリジン－２－イル）－５－（（トリフルオロメチル）スルフィニル）ベンゾ［ｄ］オキサゾールの結晶

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