WO2003089433A1 - 5,6-diphenylimidazo [1,2-a] pyrimidine et composition bactericide la renfermant - Google Patents

5,6-diphenylimidazo [1,2-a] pyrimidine et composition bactericide la renfermant Download PDF

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Publication number
WO2003089433A1
WO2003089433A1 PCT/JP2003/002014 JP0302014W WO03089433A1 WO 2003089433 A1 WO2003089433 A1 WO 2003089433A1 JP 0302014 W JP0302014 W JP 0302014W WO 03089433 A1 WO03089433 A1 WO 03089433A1
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group
compound
formula
atom substituted
imidazopyrimidine
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PCT/JP2003/002014
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English (en)
Japanese (ja)
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Hiroshi Ikegami
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Sumitomo Chemical Company, Limited
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Priority to AU2003211651A priority Critical patent/AU2003211651A1/en
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Definitions

  • the present invention relates to 5,6-diphenylimidazo [1,2-a] pyrimidine and a bactericidal composition containing the same.
  • Japanese Patent Application Laid-Open No. 2001_43978 discloses an imidazo [1,2-a] pyrimidine represented by the following formula:
  • ⁇ 1 ⁇ 5 is a hydrogen atom, a halogen atom, a linear, branched or cyclic alkyl group, a linear, branched or cyclic alkoxy group, a substituted or unsubstituted Ararukiru group, a substituted or unsubstituted Ariru group, a substituted or unsubstituted Ararukiruokishi group, there have represents a substituted or unsubstituted Ariruokishi group, further, X and chi 2, chi 3 and chi 4, and chi 4 with an adjacent group selected from chi 5 are each It may combine to form a substituted or unsubstituted carbocyclic aliphatic ring or a substituted or unsubstituted carbocyclic aromatic ring together with a substituted carbon atom. ],
  • An object of the present invention is to provide a novel imidazo [1,2-a] pyrimidine having excellent control activity against plant diseases. Disclosure of the invention
  • R 1 and R 2 represent a halogen atom
  • R 4 represents a halogen atom, a CI—C4 alkyl group, a C 1—C4 alkoxy group or a cyano group
  • R 5 represents a halogen atom, a nitro group, a cyano group.
  • a fungicidal composition containing the compound of the present invention as an active ingredient, and a method for controlling plant diseases by applying the compound of the present invention to plants or soil.
  • substituents represented by RR 2 , R 4 or R 5 are shown below.
  • halogen atom represented by R 1 and R 2 examples include a fluorine atom and a chlorine atom
  • Examples of the halogen atom represented by R 4 include a chlorine atom and a bromine atom, and examples of the C 1 -C 4 alkyl group include a methyl group, an ethyl group, a propyl group, and an isopropyl group; Examples of the C 1 -C 4 alkoxy group represented by include a methoxy group, an ethoxy group, a propyloxy group and an isopropyloxy group.
  • halogen atom represented by R 5 examples include a fluorine atom, a chlorine atom and a bromine atom,
  • Examples of the C 1 -C 4 alkyl group represented by R 5 include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, an isobutyl group and a tert-butyl group.
  • Examples of the C 1 -C 4 alkoxy group represented by R 5 include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, and a butoxy group.
  • Examples of the C 1 -C 4 alkylthio group represented by R 5 include a methylthio group, an ethylthio group, a propylthio group, and an isopropylthio group.
  • Examples of the C 1 -C 4 haloalkylthio group represented by R 5 include a trifluoromethylthio group and a 1,1,2,2-tetrafluoroethylthio group,
  • Examples of the C 1 -C 4 haloalkyl group represented by R 5 include a trifluoromethyl group
  • the C 1 one C 4 haloalkoxy group represented by R 5 for example Torifuruorome butoxy group and 1, 1, 2, 2-tetrafluoropropoxy O b ethoxy group, and
  • Examples of the CI—C 4 acyl group represented by R 5 include a formyl group, an acetyl group and a propionyl group.
  • the C 2 -C 5 alkoxycarbonyl group represented by R 5 includes, for example, a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, an isopropoxycarbonyl group and a butoxycarbonyl group.
  • examples of the phenyl group substituted by (R ⁇ and: 2 include 2-fluorophenyl group, 2-chlorophenyl group, 2,3-difluorophenyl group, and 2,3-dichlorophenyl Group, 2,4-difluorophenyl group, 2-chloro-4-fluorophenylinole group, 4-chlorophenyl_2-fluorophenyl group, 2,4-dichlorophenol group, 2,5-diphenylolenophenyl Nore group, 2,5-dichlorophenol group, 2,6-diphenoleno group, 2-chloro-6-phenylolephenyl group, 2,6-chlorophenol group, 2,3, 4-Mono-trifluorophenyl group, 2, 3, 5- Trifluorophenyl group, 2,4,5-trifluorophenyl group, 2,3,6-trifluorophenyl group, 2,4,6-trifluorophenyl group, 2-chloropheny
  • phenyl group substituted by (R 5 ) n in the formula (1) Is, for example, phenyl, 4-methylphenyl, 3_methylphenyl, 2-methylphenyl group, 4-ethynolephenyl group, 4-propylphenyl group, 4-isopropylphenyl group, 4-butylphenyl group, 41-sec-butynolephenyl group, 4-isobutylphenyl group, 4-tert-butynolephenyl group 2,3-Dimethylphenol group, 2,4-Dimethylphenyl group, 2,5-Dimethyl / lephenyl group, 3,4-Dimethylphenyl group, 3,5-Dimethylphenyl group, 4- Phenylphenyl group, 4-chlorophenyl group, 3-chlorophenyl group, 2-chlorophenyl group, 4-phenololenophenyl group, 3-fluorophenyl group, 2-fluorophenyl group , 2, 2,
  • m is 0, m is 1, and R 1 is a halogen atom substituted at the 4- or 6-position, or m is 2, and one R 1 is An imidazopyrimidine compound which is a halogen atom substituted at the 4-position and another R 1 is a halogen atom substituted at the 6-position;
  • m is 1 or 2, and at least one R 1 is a halogen atom substituted at the 4- or 6-position; an imidazopyrimidine compound;
  • n 0, or m is 1, and R 1 is a halogen atom substituted at the 4-position, an imidazopyrimidine compound;
  • m is 1 and R 1 is a halogen atom substituted at the 6-position, or m is 2 and one R 1 is a halogen atom substituted at the 4-position, and An imidazopyrimidine compound, wherein the other R 1 is a halogen atom substituted at the 6-position;
  • m is 1, and R 1 is a fluorine atom or a chlorine atom substituted at the 6-position, or m is 2 and one R 1 is substituted at the 4-position.
  • a chlorine atom and another: an imidazopyrimidine compound in which R 1 is a fluorine atom or a chlorine atom substituted at the 6-position;
  • m is 1, and R 1 is a halogen atom substituted at the 6-position, an imidazopyrimidine compound;
  • m is 1, and R 1 is a fluorine atom substituted at the 4-position, an imidazopyrimidine compound;
  • m 2, one R 1 is a fluorine atom substituted at the 3-position, and another R 1 is a chlorine atom substituted at the 6-position.
  • m 2, one of R 1 is a chlorine atom substituted at the 4-position, imidazopyrimidine compound is a chlorine atom of another R 1 is substituted with 6-position;
  • an imidazopyrimidine compound in which R 2 is a fluorine atom In the formula (1), an imidazopyrimidine compound in which R 2 is a chlorine atom;
  • an imidazopyrimidine compound in which 1 and R 2 are each independently a fluorine atom or a chlorine atom, and m is an integer of 0 to 2;
  • m is 0, m is 1, and R 1 is a fluorine atom substituted at the 4- or 6-position or a chlorine atom substituted at the 4- or 6-position, or M is 2, one R 1 is a fluorine atom substituted at the 4-position or a chlorine atom substituted at the 4-position, and another R 1 is a fluorine atom substituted at the 6-position or substituted at the 6-position Imidazopi limidine compound, wherein R 2 is a fluorine atom or a chlorine atom;
  • m is 1 or 2
  • at least one R 1 is a fluorine atom substituted at the 4- or 6-position or a chlorine atom substituted at the 4- or 6-position
  • R 2 is fluorine Imidazopyrimidine compounds which are atoms or chlorine atoms
  • m is 1, and R 1 is a fluorine atom or a chlorine atom substituted at the 6-position, or m is 2, and one R 1 is a fluorine atom substituted at the 4-position.
  • R 1 is a fluorine atom or a chlorine atom substituted at the 6-position
  • one R 1 is a fluorine atom substituted at the 4-position.
  • an imidazopyrimidine in which a chlorine atom substituted in the 4-position, another R 1 is a fluorine atom substituted in the 6-position or a chlorine atom substituted in the 6-position, and R 2 is a fluorine atom or a chlorine atom Compound;
  • an imidazopyrimidine compound wherein m is 1, R 1 is a fluorine atom substituted at the 4-position or a chlorine atom substituted at the 4-position, and R 2 is a fluorine atom or a chlorine atom;
  • an imidazopyrimidine compound wherein m is 1, R 1 is a phthalene atom substituted at the 6-position or a chlorine atom substituted at the 6-position, and R 2 is a fluorine atom or a chlorine atom;
  • m is 2, and one R 1 is a fluorine atom substituted at the 4-position or Is a chlorine atom substituted at the 4-position, another R 1 is a fluorine atom substituted at the 6-position or a chlorine atom substituted at the 6-position, and R 2 is a fluorine atom or a chlorine atom;
  • an imidazopyrimidine compound in which R 1 and R 2 are a fluorine atom and m is an integer of 0 to 2;
  • m is 1,: force R 1 is a fluorine atom substitution in the 4-position or 6-position, or,, m is 2, one of: 1 Is a fluorine atom substituted at the 4-position, and another: an imidazopyrimidine compound in which 1 is a fluorine atom substituted at the 6-position, and further R 2 is a fluorine atom;
  • an imidazopyrimidine compound in which m is 1 or 2, at least one R 1 is a fluorine atom substituted at the 4- or 6-position, and R 2 is a fluorine atom;
  • m is 1 and R 1 is a fluorine atom substituted at the 6-position, or m is 2 and one R 1 is a fluorine atom substituted at the 4-position.
  • m is 1, R 1 is a fluorine atom substituted at the 6-position, and R 2 is a fluorine atom, an imidazopyrimidine compound;
  • m is 2, one R 1 is a fluorine atom substituted at the 4-position, another R 1 is a fluorine atom substituted at the 6-position, and R 2 is a fluorine atom An imidazopyrimidine compound;
  • m is 1, R 1 is a fluorine atom substituted at the 6-position, and R 2 is a chlorine atom, an imidazopyrimidine compound;
  • an imidazopyrimidine compound in which R 4 is a methyl group in the formula (1): an imidazopyrimidine compound in which R 4 is an alkoxy group; in the formula (1), R 4 is a methoxy group
  • m is an integer of 0 to 2
  • R 4 is a halogen atom, an imidazo pyrimidine compound
  • m is 0 or m is 1, and R 1 is a halogen atom substituted at the 4- or 6-position ⁇ or m is 2, and one R 1 is An imidazopyrimidine compound in which the halogen atom is substituted at the 4-position, another R 1 is a halogen atom substituted at the 6-position, and R 4 is a halogen atom;
  • im is an imidazopyrimidine in which m is 1 or 2, at least one R 1 is a haguchigen atom substituted at the 4-position or the 6-position, and R 4 is a no-halogen atom.
  • m is 1 and R 1 is a halogen atom substituted at the 6-position, or m is 2 and one R 1 is a halogen atom substituted at the 4-position, and An imidazopyrimidine compound in which another R 1 is a Haguchigen atom substituted at the 6-position and R 4 is a Haguchigen atom;
  • m is 1, R 1 is a halogen atom substituted at the 4-position, and R 4 is a halogen atom; an imidazopyrimidine compound;
  • m is 1, an imidazopyrimidine compound in which R 1 is a halogen atom substituted at the 6-position, and R 4 is a nitrogen atom;
  • m is 2, one R 1 is a halogen atom substituted at the 4-position, another R 1 is a halogen atom substituted at the 6-position, and R 4 is a nitrogen atom.
  • Certain imidazopyrimidine compounds In the formula (1), an imidazopyrimidine compound in which R 2 is a fluorine atom and R 4 is a halogen atom;
  • m is 2, one R 1 is a halogen atom substituted at the 4-position, another R 1 is a fluorine atom substituted at the 6-position, and R 2 is a fluorine atom.
  • m is 2, one R 1 is a halogen atom substituted at the 4-position, another R 1 is a chlorine atom substituted at the 6-position, and R 2 is a chlorine atom.
  • m is 2, one R 1 is a halogen atom substituted at the 4-position, another R 1 is a fluorine atom substituted at the 6-position, and R 2 is a chlorine atom.
  • m is 2, one of 1 is a fluorine atom substituted at the 4-position, another R 1 is a fluorine atom substituted at the 6-position, and R 2 is a fluorine atom.
  • R 4 is a halogen atom; an imidazopyrimidine compound;
  • m is 2, one R 1 is a chlorine atom substituted at the 4-position, another R 1 is a chlorine atom substituted at the 6-position, and R 2 is a chlorine atom.
  • R 2 is a fluorine atom or a chlorine atom
  • R 4 is a chlorine atom
  • a fluorine atom or a chlorine atom and R 1 and R. 2 are each independently, imidazopyrimidine compounds wherein R 4 is a chlorine atom;
  • R 1 and R 2 are each independently a fluorine atom or a chlorine atom, m is an integer of 0 to 2, and: an imidazopyrimidine compound in which R 4 is a chlorine atom;
  • m is 0, m is 1, and R 1 is a fluorine atom substituted at the 4- or 6-position or a chlorine atom substituted at the 4- or 6-position, or M is 2, one R 1 is a fluorine atom substituted at the 4-position or a chlorine atom substituted at the 4-position, and another R 1 is a fluorine atom substituted at the 6-position or substituted at the 6-position
  • m is 1 or 2
  • at least one R 1 is a fluorine atom substituted at the 4- or 6-position or a chlorine atom substituted at the 4- or 6-position
  • R 2 is An imidazo pyrimidine compound in which 4 is a chlorine atom
  • m is 1, and R 1 is a fluorine atom substituted at the 6-position or a chlorine atom substituted at the 6-position, or m is 2, and one of: R 1 is at the 4-position R 1 is a fluorine atom substituted at the 6-position or a chlorine atom substituted at the 6-position, and R 2 is a fluorine atom or a chlorine atom substituted at the 6-position.
  • m is 1, R 1 is a fluorine atom substituted at the 6-position or a chlorine atom substituted at the 6-position, R 2 is a fluorine atom or a chlorine atom, and R 4 is a chlorine atom.
  • m is 2, and one of: R 1 is a fluorine atom substituted at the 4-position or a chlorine atom substituted at the 4-position, and another R 1 is a fluorine atom substituted at the 6-position.
  • R 1 is a fluorine atom substituted at the 4-position or a chlorine atom substituted at the 4-position
  • another R 1 is a fluorine atom substituted at the 6-position.
  • an imidazopyrimidine compound which is a chlorine atom substituted at the 6-position
  • R 2 is a fluorine atom or a chlorine atom
  • R 4 is a chlorine atom
  • R 1 and R 2 are fluorine atoms, and R 4 is a chlorine atom.
  • Dazopyrimidine compounds
  • an imidazopyrimidine compound in which R 1 and R 2 are a fluorine atom, m is an integer of 0 to 2, and R 4 is a chlorine atom;
  • m is 0 or m is 1 and R 1 is a fluorine atom substituted at the 4- or 6-position ⁇ or m is 2 and one R 1 is An imidazopyrimidine compound in which a fluorine atom substituted in the 4-position, another R 1 is a fluorine atom substituted in the 6-position, R 2 is a fluorine atom, and R 4 is a chlorine atom; )), Wherein m is 1 or 2, at least one R 1 is a fluorine atom substituted at the 4- or 6-position, R 2 is a fluorine atom, and R 4 is a chlorine atom. ;
  • m 1, R 1 is a fluorine atom substituted at the 4-position, R 2 is a fluorine atom, and R 4 is a chlorine atom; an imidazopyrimidine compound; an imidazopyrimidine compound in which m is 1, R 1 is a fluorine atom substituted at the 6-position, R 2 is a fluorine atom, and is a chlorine atom; In the formula (1), m is 2; An imidazopyrimidine compound in which R 1 is a fluorine atom substituted at the 4-position, another R 1 is a fluorine atom substituted at the 6-position, and 2 is a fluorine atom and R 4 is a chlorine atom;
  • m is 1, R 1 is a halogen atom substituted at the 6-position, and R 4 is a chlorine atom, an imidazopyrimidine compound;
  • m is 2, one R 1 is a halogen atom substituted at the 4-position, another R 1 is a halogen atom substituted at the 6-position, and R 4 is a chlorine atom.
  • m is 2, one of: R 1 is a halogen atom substituted at the 3-position, and another: R 1 is a halogen atom substituted at the 6-position, and R 4 is a chlorine atom.
  • n is 1, and R 5 is an imidazopyrimidine compound
  • n is 1, and R 5 is a C 1 -C 4 alkyl group, an imidazopyrimidine compound
  • n 0, 1 or 2
  • R 5 is a halogen atom, C 1 -C 4 alkyl group, C 1 -C 4 is an imidoalkyl group or a C 1 -C 4 alkoxy group.
  • compound (2) o a compound represented by the formula (2) (hereinafter, referred to as compound (2) o)
  • R 2 , R m and n represent the same meaning as described above, and R 4 ° represents a halogen atom or a C 1 -C 4 alkyl group.
  • compound (3) Is a compound represented by the formula (3) (hereinafter, referred to as compound (3)):
  • R 1 R 2 , R 4 ° and m represent the same meaning as described above, and X 1 represents a halogen atom (for example, a chlorine atom or the like). ]
  • the reaction is usually performed in a solvent in the presence of a base.
  • the solvent used in the reaction include ethers such as methinolate tert-butyl ether, ethylene glycol dimethinole ether, tetrahydrofuran and 1,4-dioxane, and aliphatic hydrocarbons such as hexane, heptane and octane. And aromatic hydrocarbons such as toluene, xylene and the like, nitriles such as acetonitrile and butyronitrile, water and a mixture thereof.
  • Examples of the palladium catalyst used in the reaction include palladium acetate, tetrakistrifuedinolephosphine palladium, ⁇ 1,1′-bis (diphen-norephosphino) phenoctene ⁇ dioctane palladium (II) methylene chloride complex, bis chloride ( bird Phenylphosphine) palladium, salted-on ⁇ 1,4-bis (diphenylenophosphinobutane) ⁇ palladium and ⁇ 1,3-bis (diphenylphosphino) propane chloride ⁇ palladium.
  • Examples include sodium bicarbonate, potassium bicarbonate, sodium carbonate, potassium carbonate, sodium phosphate and potassium phosphate.
  • the compound (4) is usually used in an amount of 1 to 2 mol
  • the palladium catalyst is usually used in an amount of 0.001 to 0.1 monol
  • the base is usually used in an amount of 2 to 20 mol per 1 mol of the compound (3). Is done.
  • the reaction temperature of the reaction is usually in the range of 20 to 120 ° C, and the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound of the present invention represented by the formula (2) is subjected to post-treatment operations such as pouring the reaction mixture into water, extracting with an organic solvent, and drying and concentrating the obtained organic layer. Can be isolated.
  • the isolated compound of the present invention represented by the formula (2) can be further purified by chromatography, recrystallization and the like.
  • compound (5) a compound represented by the formula (5) (hereinafter referred to as compound (5)
  • the reaction may be carried out in the presence of a solvent.
  • a solvent examples include nitriles such as acetonitrinole, propionitrile, methyl-tert-butylatenoate, ethylene glycolone methinoleatenoate, tetrahydrofuran, 1 Ethers such as 1,4-dioxane; amides such as N, N-dimethylformamide; and sulfoxides such as dimethyl sulfoxide.
  • Examples of the metal cyanide used in the reaction include potassium cyanide, sodium cyanide and the like.
  • the metal cyanide is usually used in a proportion of 1 mol to 10 mol per 1 mol of the compound (6).
  • a crown ether such as 18_crown-16, dibenzo-18-crown-16, dicyclohexano 18-crown-16, 15-crown-15 may be used in the reaction, if necessary.
  • the crown ether is usually used in a proportion of 1 mol to 10 mol per 1 mol of the compound (6).
  • the reaction temperature of the reaction is usually in the range of 20 to 150 ° C, and the reaction time is usually in the range of 1 to 48 hours.
  • the reaction mixture is poured into water, extracted with an organic solvent, and the obtained organic layer is subjected to post-treatment operations such as drying and concentration to obtain the present invention represented by the formula (5).
  • the compound can be isolated.
  • the isolated compound of the present invention represented by the formula (5) can be further purified by chromatography, recrystallization and the like.
  • compound (7) a compound represented by the formula (7) (hereinafter referred to as compound (7)
  • R 1 R 2 , R 5 , m and n represent the same meaning as described above, and R 41 represents a C 1 -C 4 alkyl group.
  • the reaction is usually performed in a solvent.
  • solvent used in the reaction include ethers such as methanol, tert-butylinoleate, ethylene glycolone resin methinoleate, tetrahydrofuran, 1,4-dioxane and the like; N, N-dimethylformamide and the like.
  • ethers such as methanol, tert-butylinoleate, ethylene glycolone resin methinoleate, tetrahydrofuran, 1,4-dioxane and the like
  • N N-dimethylformamide and the like.
  • R 41 an alcohol corresponding to the metal alkoxide compound used: R 41 ⁇ H wherein R 41 has the same meaning as described above. ].
  • R 41 OM is an alcohol: R 41 OH and an alkali metal (eg, lithium, sodium, potassium) or an alkali metal hydride (eg, lithium hydride, sodium hydride, hydrogen) Chemical strength). Usually, sodium alkoxide is used.
  • the metal alkoxide compound is generally used in a proportion of 1 mol to 5 mol per 1 mol of compound (6).
  • the reaction temperature of the reaction is usually in the range of 0 to 100 ° C, and the reaction time is usually in the range of 1 to 48 hours.
  • the reaction mixture is poured into water and extracted with an organic solvent, and the obtained organic layer is subjected to a post-treatment operation such as drying and concentration to obtain the present invention represented by the formula (7).
  • the compound can be isolated.
  • the isolated compound of the present invention represented by the formula (7) can be further purified by chromatography, recrystallization and the like.
  • compound (9) a compound represented by the formula (9) (hereinafter, referred to as compound (9)) can be produced, for example, by a route shown in the following scheme.
  • R 4 2 is C: represents a C 4 alkyl group.
  • the compound represented by formula (8) (hereinafter referred to as compound (8)) can be produced by reacting compound (6) with dialkyl malonate in the presence of a base.
  • the reaction is usually performed in a solvent.
  • solvent used in the reaction include ether's such as methylenolate tert-butylinoleatene, ethylene glycolone resin methinoleatenole, tetrahydrofuran, 1,4-dioxane, and N, N-dimethylhonolemamide.
  • base used in the reaction include alkali metal hydrides such as sodium hydride.
  • the dialkyl malate is generally used in a proportion of 2 to 8 mol, and the base is usually used in a proportion of 2 to 8 mol per 1 mol of the compound (6).
  • the reaction temperature of the reaction is usually in the range of 0 to: 150 ° C, and the reaction time is usually in the range of 1 to 48 hours.
  • the reaction mixture is poured into acidic water (for example, hydrochloric acid, aqueous solution of citric acid, etc.), extracted with an organic solvent, and subjected to a post-treatment operation such as drying and concentration of the obtained organic layer.
  • acidic water for example, hydrochloric acid, aqueous solution of citric acid, etc.
  • organic solvent for example, aqueous solution of citric acid, etc.
  • the compound (8) can be isolated. Isolated compound ( 8) can be further purified by chromatography, recrystallization and the like.
  • Compound (9) can be produced by thermally decomposing compound (8).
  • the reaction is usually carried out in a strong acid aqueous solution (hydrochloric acid, sulfuric acid, etc.), the reaction temperature is usually in the range of 50 to 100 ° C, and the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound (9) can be isolated by performing post-treatment operations such as neutralizing the reaction solution, extracting with an organic solvent, and drying and concentrating the obtained organic layer.
  • the isolated compound (9) can be further purified by chromatography, recrystallization and the like.
  • the compound represented by the formula (A-3) (hereinafter, referred to as compound (A-3)) can be produced, for example, by a route shown in the following scheme.
  • the compound represented by the formula (A-2) (hereinafter, referred to as compound (A-2)) is a malonic acid ester ⁇ ⁇ conjugated compound represented by the formula (A-1) (hereinafter, referred to as compound ( ⁇ -1) ) And 2-aminoimidazole hydrochloride in the presence of a base. can do.
  • the reaction can also be performed in the presence of a solvent.
  • a solvent examples include aromatic hydrocarbons such as xylene and mesitylene and acid amides such as N, N-dimethylformamide.
  • Examples of the base used in the reaction include triptylamine, 1,8-diazabicyclo [5.4.0] indeck-17-ene (hereinafter, referred to as DBU), 1,5-diazabicyclo [4.3.0] ] Organic bases such as non-5-ene (hereinafter referred to as DBN).
  • 2-aminoimidazolone hydrochloride is usually used in a proportion of 0.5 to 2 mol, and a base is usually used in a proportion of 1.5 to 3 mol, per 1 mol of the compound (A-1).
  • the reaction temperature of the reaction is usually in the range of 50 to 200 ° C, and the reaction time is usually in the range of 0.5 to 24 hours.
  • the reaction mixture is partitioned between an organic solvent and water (or alkaline water), and a precipitate formed by adding an acid such as hydrochloric acid to the obtained aqueous layer (after concentrating as necessary).
  • the compound (A-2) can be isolated by filtering.
  • the compound (A-12) can be isolated in the form of a salt by filtering the reaction mixture as it is or, if necessary, concentrating it.
  • Step 2-1 The reaction of Step 2-1 can be carried out similarly by using 2-aminoimidazole sulfate instead of 2-aminoimidazole hydrochloride.
  • Compound (A-3) can be produced by reacting compound (A-2) with a halogenating agent.
  • the reaction can be performed in the presence of a solvent.
  • a solvent examples include aromatic hydrocarbons such as toluene and xylene, nitrinoles such as acetonitrile and propionitolinole, and halogenated hydrocarbons such as 1,2-dichloroethane.
  • halogenating agent used in the reaction for example, an organic phosphorus compound:
  • X 1 has the same meaning as described above. Specific examples include phosphorus oxychloride and the like].
  • the halogenating agent used in the reaction is usually 2 mol to an excess amount per 1 mol of the compound (A-2).
  • Organic bases such as 2-picoline, DBU, and DBN can also be allowed to coexist.
  • the amount of the base used is usually 0.1 to 5 mol per 1 mol of the compound (A-2). .
  • the reaction temperature of the reaction is usually in the range of 50 to 150 ° C, and the reaction time is usually in the range of 1 to 48 hours.
  • the reaction mixture is directly concentrated, and the obtained residue is separated with an organic solvent and a weakly basic aqueous solution (for example, aqueous sodium hydrogen carbonate).
  • a weakly basic aqueous solution for example, aqueous sodium hydrogen carbonate.
  • the compound represented by the formula (A-3) can be isolated.
  • the isolated compound represented by the formula (A-3) can be further purified by chromatography, recrystallization, or the like.
  • the compound represented by the formula (B-3) (hereinafter, referred to as compound (B-3)) can be produced, for example, by a route shown in the following scheme.
  • RR 2 , R 6 , X 1 and m represent the same meaning as described above, and R 43 represents a C1-C4 alkyl group.
  • Process 3-1 A compound represented by the formula (B-2) (hereinafter, referred to as compound (B-2)) is represented by the formula (B-1):] 3-ketoester compound (hereinafter, referred to as compound (B-1)) ) And 2-aminoimidazole hydrochloride in the presence of a base.
  • the reaction can be performed in the presence of a solvent.
  • a solvent examples include aromatic hydrocarbons such as xylene and mesitylene and acid amides such as N, N-dimethylformamide.
  • Examples of the base used in the reaction include organic bases such as triptylamine, DBU and DBN. '
  • 2-aminoimidazole hydrochloride is usually used in a proportion of 0.5 to 2 mol, and a base is usually used in a proportion of 1.5 to 3 mol per 1 mol of the compound (B-1).
  • the reaction temperature of the reaction is usually in the range of 50 to 200 ° C, and the reaction time is usually in the range of 0.5 to 24 hours.
  • reaction mixture is partitioned between an organic solvent and water (or alkaline water), and a precipitate formed by adding an acid such as hydrochloric acid to the obtained aqueous layer (after concentrating as necessary).
  • Compound (B-2) can be isolated by filtration.
  • the compound represented by the compound (B-12) can be isolated in the form of a salt by filtering the reaction mixture as it is or, if necessary, concentrating it.
  • Step 3-1 The reaction of Step 3-1 can be carried out in the same manner by using 2-aminoimidazole sulfate instead of 2-aminoimidazole hydrochloride.
  • Compound (B-3) can be produced by reacting compound (B-2) with a halogenating agent. '
  • the reaction can also be performed in the presence of a solvent.
  • a solvent examples include aromatic hydrocarbons such as toluene and xylene, nitriles such as acetoethryl and propionitrile, and halogenated hydrocarbons such as 1,2-dichloropropane.
  • halogenating agent used in the reaction for example, an organic phosphorus compound: ⁇ [wherein, X 1 has the same meaning as described above. More specifically, for example, can give.
  • the amount of the halogenating agent used in the reaction is usually 1 mol to an excess amount per 1 mol of the compound represented by the formula (B-2).
  • an organic base such as N, N-dimethylaniline, N, N-getylaniline, triethylamine, diisopropylethylamine, pyridine, 5-ethyl-2-picoline, DBU, or DBN may be used in the reaction.
  • the amount of the base is 0.1 to 5 monoles per 1 mol of the compound represented by the formula (B-2).
  • the reaction temperature of the reaction is usually in the range of 50 to 150 ° C, and the reaction time is usually in the range of 1 to 48 hours.
  • compound (B-3) can be isolated.
  • the isolated compound (B-3) can be further purified by chromatography, recrystallization, or the like.
  • the compound (4) can be produced, for example, according to the method described on page 68 of Org Anic Synthes Synthes Colls.
  • Compound (A-1) can be produced, for example, according to the method described in Japanese Patent Application Laid-Open No. 2-202876, Chemistry Let Lets, 1981, p. 367.
  • the compound (B-1) can be prepared, for example, according to the method described in, for example, Organic Synthesis Collective Volume 2, pp. 487-489 and 284-286, Japanese Patent Application Laid-Open No. 60-255788. It can be manufactured according to it.
  • Wheat spikelets (Erysiphe graminis), redness, rot (Gibbere ⁇ la zeae), rust (Puccinia striiformis, P. graminis, P. recondita, P. hordei), 3 ⁇ 4 rot (Typhula sp., Micronectriella nivalis), smut (Ustilago tritici, U. nuda), black smut (Tilletia caries), eye spot (Pseudocercosporella herpotrichoides), scald (Rhynchosporium secalis), leaf blight (Septoria tritic ⁇ ) (Leptosphaeria nodorum);
  • Grape scab (Elsinoe ampelina), rot (Glomerella cingulataj), powdery mildew (Unc inula necator), rust (Phakopsora ampe ⁇ opsiais), bukkake rot (Guignardia bidwellii), and bets and pings (Plasmopara viticola) );
  • Anthracnose (colletotrichum lagenarium), powdery mildew
  • Tomato no Rinhei Alternaria solani
  • Scab Shu adosporium fulvumj
  • Plague Phytophthora infestans
  • Green onion rust (Puccinia allii), soybean purpura (Cercospora kikuchii), black rot (Elsinoe glycines), black spot (Diaporthe phaseolorum var. Sojae); Kingen's anthracnose (Colletotrichum lindemthianum);
  • Potato summer plague (Alternaria solani), plague (Phytophthora infestans);
  • Gray rot (Botrytis cinerea), sclerotium (Sclerotinia sc ⁇ erotiorunv 0 ) on various crops
  • the compound of the present invention exerts a bactericidal effect even when it is applied to plants or soil, but is usually used in the form of a bactericidal composition containing the compound of the present invention and a suitable carrier.
  • the germicidal composition of the present invention is usually prepared by mixing the compound of the present invention with a solid carrier and / or a liquid carrier, and adding a surfactant or other formulation aid as necessary, to prepare an emulsion, a wettable powder, It is prepared as preparations such as wettable powders, flowables, powders, and granules. In these preparations, the compound of the present invention is usually contained at 0.1 to 90% by weight.
  • solid carrier used in the formulation examples include kaolin clay, attaparjait clay, bentonite, montmorillonite, acid clay, pyrophyllite, tanolek, diatomaceous earth, calcite and other minerals, corn cob powder, walnut shell powder, etc.
  • the liquid carrier include xylene, Aromatic hydrocarbons such as alkylbenzene, methylnaphthalene, etc., alcohols such as 2-propanol, ethylene glycol, propylene glycol, cellosolve, ketones such as acetone, cyclohexanone, isophorone, soybean oil, cottonseed oil, etc.
  • Vegetable oil, petroleum aliphatic hydrocarbon , Ester le include dimethyl sulfoxide, Asetonitoriru and water.
  • Surfactants include, for example, alkyl sulfates, alkylaryl sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkylaryl etherenolate phosphate, lignin snolephonate, naphthalene sulfonate polyaldehyde polycondensates And the like, and nonionic surfactants such as polyoxyethylene alkenyl oleoretinol, polyoxyethylene olenoquinole polyoxypropylene block copolymer, and sorbitan fatty acid ester.
  • Other pharmaceutical auxiliaries include, for example, water-soluble polymers such as polybutyl alcohol and polybutylpyrrolidone, gum arabic, alginic acid and its salts, polysaccharides such as CMC (Ruboxymethylcenorellose), xanthan gum, and aluminum magnesium. ⁇ Inorganic substances such as silicate and alumina sol, preservatives, coloring agents and stabilizers such as PAP (isopropyl acid phosphate) and BHT.
  • PAP isopropyl acid phosphate
  • BHT isopropyl acid phosphate
  • the amount of treatment can be varied depending on the type of crop as a plant to be controlled, the type of disease to be controlled, the degree of occurrence of the disease to be controlled, formulation, treatment time, weather conditions, etc.
  • the compound of the present invention is usually 1 to 500 g, preferably 5 to 100 g per l′ OOOO m 2 .
  • Emulsions, wettable powders, flowables, etc. are usually treated by diluting with water and spraying.
  • concentration of the compound of the present invention is generally in the range of 0.001 to 3% by weight, preferably in the range of 0.0 'to 5-1% by weight. Dusts, granules, etc. are usually processed without dilution.
  • the plant When the fungicidal composition of the present invention is applied to a plant, the plant can be protected from plant diseases by treating the plant at the seed stage.
  • a specific method for example, a method of immersing a seed in a fungicidal composition of the present invention prepared by adjusting the concentration of the compound of the present invention to 1 to 100 ppm, The method includes spraying or smearing the fungicidal composition of the present invention at a concentration of l to 100 ppm, and coating the seed of a plant with the fungicidal composition of the present invention.
  • the method for controlling plant diseases of the present invention is generally carried out by applying an effective amount of the bactericidal composition of the present invention to a plant in which the occurrence of a disease is predicted or a soil in which the plant grows.
  • the fungicidal composition of the present invention is generally used as an agricultural / horticultural fungicide, that is, a fungicide for controlling plant diseases in fields, paddy fields, orchards, tea fields, pastures, lawns, and the like.
  • the fungicidal compositions of the present invention can also be used with other fungicides, insecticides, acaricides, nematicides, herbicides, plant growth regulators and / or fertilizers.
  • Such fungicides include, for example, propiconazole, triazimenol, prochloraz, penconazo monole, tebuconazonole, funoresilazonole, dinicozonore, bromconazonole, epoxyconazo monole, difuenoconazonole, ciproconazole Azole propagating compounds such as triflumizole, tetraconazole, microbutanol, fenbuconazole, hexaconazole, fluquinconazole, triconazole, bitertanol, imazalil and flutoriaphor; fenpropimorph, tridemorph and phen Cyclic amine fungicidal compounds such as providin; benzimidazole fungicidal compounds such as carbendazim, benomyl, thiabendazole, and thiophane monomethyl; Shimidon; Shipurodi two Nore; Pyrimethanil; Jet
  • the residue was dissolved in a mouth-mouth form and washed successively with water, a 10% aqueous sodium hydroxide solution, water, a saturated aqueous sodium chloride aqueous solution, and water.
  • the organic layer was dried over anhydrous sodium sulfate and concentrated.
  • the residue was subjected to silica gel gel chromatography.
  • the obtained crude product was dissolved in ethyl alcohol (2 ml), hydrazine monohydrate (34 mg) was added, and the mixture was stirred at room temperature for 2 hours.
  • reaction solution was poured into water, and the deposited precipitate was collected by filtration and subjected to silica gel column chromatography to give 5- (4-methoxyphenyl) -16- (2,4,6-trifluorophenyl) One 7-cloth imidazo [1, 2-a] pyrimidine
  • the obtained crude product is mixed with 5 ml of ethyl alcohol and 5 ml of aqueous ammonia, and heated under reflux for 2 hours. did.
  • the reaction mixture was allowed to cool to room temperature, poured into a 10% aqueous solution of taenoic acid, and extracted with methyl tert-butyl ether.
  • the organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated.
  • the residue was subjected to silica gel gel column chromatography to give 5- (3-methylphenyl) -1-6- (2,4,6-trifluorophenyl) -7-chloroimidazo [1,2-a] pyrimidine
  • reaction mixture was allowed to cool to room temperature, poured into a 10% aqueous sodium hydroxide solution, and extracted with methyl tert-butyl ether. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated. After the residue was subjected to silica gel column chromatography, the obtained crude product was mixed with 3 ml of ethyl alcohol and 3 ml of aqueous ammonia, and heated under reflux for 1.5 hours.
  • the obtained crude product was mixed with 5 ml of ethanolic ethanol and 5 ml of aqueous ammonia, and heated under reflux for 3 hours.
  • the reaction mixture was allowed to cool to room temperature, poured into a 10% aqueous solution of citric acid, and extracted with methyl tert-butyl ether.
  • the organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated.
  • the obtained crude product was mixed with 10 ml of ethyl alcohol and 5 ml of aqueous ammonia, and heated under reflux for 18 hours. reaction The mixture was allowed to cool to room temperature, poured into a 10% aqueous solution of citric acid, and extracted with methyl-tert-butyl ether. The organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated.
  • each of the compounds of the present invention (1) to (24) 50 parts of each of the compounds of the present invention (1) to (24), 3 parts of calcium ligninsulfonate, 2 parts of magnesium lauryl sulfate and 45 parts of synthetic hydrous silicon dioxide are thoroughly pulverized and mixed to obtain each wettable powder. Get.
  • Each of the present compounds (1) to (24) is mixed well with 5 parts of each, 14 parts of polyoxyethylene styryl phenol olenoether, 6 parts of calcium dodecylbenzenesulfonate and 75 parts of xylene to obtain each emulsion.
  • each of the compounds (1) to (24) of the present invention 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of olcin clay, water may be added. Each granule is obtained by kneading and granulating and drying.
  • Comparative compound A Were filled with sandy loam, sown with cucumber (Sagami Hanjiro), and grown in a greenhouse for 10 days.
  • Each of the preparations of the compounds of the present invention (1) to (24) and Comparative Compound A obtained according to Formulation Example 6 was diluted with water to a concentration of 500 ppm to prepare a spray liquid.
  • Each spray solution was sprayed on the foliage so as to be sufficiently adhered to the above-mentioned cucumber cotyledon surface. After the spray solution on the foliage was air-dried, a PDA medium containing the spores of Botrytis cinerea was placed on the cotyledon of Cucumber. After leaving the cucumber in a humid environment at 12 ° C for 5 days, the lesion area of the plant was visually observed. The lesion area of untreated plants was compared with the lesion area of plants treated with the drug, and the disease control effect was determined.
  • the lesion area of cucumber treated with a spray liquid containing the present compounds (1) to (24) as an active ingredient was 30% or less of the lesion area of the untreated group.
  • the lesion area of the cucumber treated with the spray liquid containing the comparative compound was 75% or more of the lesion area of the untreated group.
  • each of the comparative compound A and the compound 22 dissolved in dimethyl sulfoxide was mixed with a PDA medium to a predetermined concentration (2 ppm), and poured into a sterile petri dish to prepare a plate medium.
  • a piece of mycelium of a fungus of gray mold was inoculated in the center of the prepared medium, and cultured at 18 ° C for 60 hours, and then the flora radius was measured.
  • the radius of the flora in the PDA medium supplemented with Compound 22 was 10% or less of the radius of the flora in the PDA medium supplemented without Compound 22.
  • Comparative compound Radish flora in PDA medium with kazuri A It was more than 80% of the radius of the flora. .
  • plant diseases can be controlled.

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  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Plant Pathology (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

L'invention concerne une imidazopyrimidine représentée par la formule (1), dans laquelle R1 et R2 désignent chacun un halogéno ; R4 désigne un halogéno, etc. ; R5 désigne un halogéno, nitro, etc. ; m est un nombre entier compris entre 0 et 4 ; n est un nombre entier compris entre 0 et 5 ; et lorsque m est un nombre entier égal ou supérieur à 2, les groupes R1 peuvent être les mêmes atomes ou des atomes différents, et lorsque n est un nombre entier égal ou supérieur à 2, les groupes R5 peuvent être les mêmes atomes ou groupes ou des atomes ou des groupes différents. Le composé de l'invention présente une excellente activité bactéricide contre les maladies des plantes.
PCT/JP2003/002014 2002-04-19 2003-02-25 5,6-diphenylimidazo [1,2-a] pyrimidine et composition bactericide la renfermant WO2003089433A1 (fr)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1431299A1 (fr) * 2001-09-04 2004-06-23 Sumitomo Chemical Company, Limited IMIDAZO(1,2-a)PYRIMIDINES ET COMPOSITIONS FONGICIDES LES CONTENANT
WO2005030218A1 (fr) * 2003-09-24 2005-04-07 Wyeth Holdings Corporation 6-aryl-7-halo-imidazo[1,2-a]pyrimidines, agents anticancereux
WO2011074677A1 (fr) * 2009-12-18 2011-06-23 石原産業株式会社 Dérivé d'imidazopyrimidine ou sel de celui-ci, et agent de lutte contre les organismes nuisibles le comprenant

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997042192A1 (fr) * 1996-05-07 1997-11-13 Basf Aktiengesellschaft Imidazoquinazolines, agents les contenant et leur utilisation dans la lutte contre les champignons nuisibles et les parasites animaux

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997042192A1 (fr) * 1996-05-07 1997-11-13 Basf Aktiengesellschaft Imidazoquinazolines, agents les contenant et leur utilisation dans la lutte contre les champignons nuisibles et les parasites animaux

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1431299A1 (fr) * 2001-09-04 2004-06-23 Sumitomo Chemical Company, Limited IMIDAZO(1,2-a)PYRIMIDINES ET COMPOSITIONS FONGICIDES LES CONTENANT
EP1431299A4 (fr) * 2001-09-04 2004-09-22 Sumitomo Chemical Co IMIDAZO(1,2-a)PYRIMIDINES ET COMPOSITIONS FONGICIDES LES CONTENANT
WO2005030218A1 (fr) * 2003-09-24 2005-04-07 Wyeth Holdings Corporation 6-aryl-7-halo-imidazo[1,2-a]pyrimidines, agents anticancereux
US7285555B2 (en) 2003-09-24 2007-10-23 Wyeth Holdings Corporation 6-aryl-7-halo-imidazo[1,2-a]pyrimidines as anticancer agents
WO2011074677A1 (fr) * 2009-12-18 2011-06-23 石原産業株式会社 Dérivé d'imidazopyrimidine ou sel de celui-ci, et agent de lutte contre les organismes nuisibles le comprenant

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