WO2010119878A1 - Pyrimidine compound and its use for pest control - Google Patents

Pyrimidine compound and its use for pest control Download PDF

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Publication number
WO2010119878A1
WO2010119878A1 PCT/JP2010/056627 JP2010056627W WO2010119878A1 WO 2010119878 A1 WO2010119878 A1 WO 2010119878A1 JP 2010056627 W JP2010056627 W JP 2010056627W WO 2010119878 A1 WO2010119878 A1 WO 2010119878A1
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Prior art keywords
halogen
group
optionally substituted
compound
pyrimidine
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PCT/JP2010/056627
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French (fr)
Inventor
Hiroki Tomioka
Hiroshi Ikegami
Daisuke Takaoka
Yoshihiko Nokura
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Sumitomo Chemical Company, Limited
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Publication of WO2010119878A1 publication Critical patent/WO2010119878A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • the present invention relates to a pyrimidine compound and its use in pest control.
  • pyrimidine compounds are known in, for example, US 2009/005403 Al, JP-A-63-039875, WO 99/41253, US 2008/132522 Al and WO 2005/019207.
  • An object of the present invention is to provide a novel compound having a control activity against pests.
  • the present inventors have studied so as to find a compound having a control activity against pests and found that a pyrimidine compound represented by the following formula (1) has a control activity against pests, thus leading to the present invention.
  • a pyrimidine compound represented by formula (1) represented by formula (1) :
  • Q represents oxygen or -S(O) n -, n represents 0, 1 or 2
  • G 1 represents nitrogen or CR 6
  • R 7 represents hydrogen or a chain C1-C6 hydrocarbon group optionally substituted with halogen, provided that R 7 is not hydrogen when L 1 is -S(O) n - and n is 1 or 2,
  • R 8 represents hydrogen, a hydroxy group, an amino group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C1-C6 alkoxy group optionally substituted with halogen, a C1-C4 alkylamino group optionally substituted with halogen, or a C2-C8 dialkylamino group optionally substituted with halogen,
  • R 9 represents hydrogen, a chain Cl-C ⁇ hydrocarbon group optionally substituted with halogen or a C1-C6 alkylsulfonyl group optionally substituted with halogen
  • R 3 represents hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, or - L 2 R 1 °
  • L 2 represents oxygen, -S(O) n - or -NR 12 -,
  • R 10 represents hydrogen or a chain C1-C6 hydrocarbon group optionally substituted with halogen, provided that R 10 is not hydrogen when L 2 is -S(O) n - and n is 1 or 2,
  • R 11 represents hydrogen, a hydroxy group, an amino group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C1-C6 alkoxy group optionally substituted with halogen, a C1-C4 alkylamino group optionally substituted with halogen, or a C2-C8 dialkylamino group optionally substituted with halogen,
  • R 12 represents hydrogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or a C1-C6 alkylsulfonyl group optionally substituted with halogen,
  • R 5 represents a Cl-ClO alkyl group substituted with one or more members selected from Group B, or a C3-C10 alkenyl group substituted with or one or more members selected from Group B
  • Group A represents the group consisting of halogen, an amino group, a cyano group, a nitro group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a Cl- C6 alkoxy group optionally substituted with halogen, and S(0)nR 13 , in which R 13 represents a C1-C6 alkyl group optionally substituted with halogen,
  • G 1 is nitrogen or CR 6 ,
  • R 1 and R 6 are the same or different and represent hydrogen, halogen or a chain C1-C6 hydrocarbon group optionally substituted with halogen,
  • R 2 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L 1 R 7 , R 3 is hydrogen or a chain C1-C6 hydrocarbon group optionally substituted with halogen,
  • R 4 is hydrogen, halogen or a chain C1-C6 hydrocarbon group optionally substituted with halogen
  • R 5 is a Cl-ClO alkyl or C3-C10 alkenyl group substituted with halogen or -L 3 R 14 ;
  • a pest controlling agent comprising the pyrimidine compound according to any one of [1] to [12] and an inert carrier;
  • a method of controlling pests which comprises a step of applying an effective amount of the pyrimidine compound according to any one of [1] to [12] to pests or habitats of the pests.
  • R 4 represents hydrogen, halogen, or a chain C1-C6 hydrocarbon group
  • R 5 represents a Cl-ClO alkyl group substituted with one or more halogen, or a C3-C10 alkenyl group substituted with one or more halogen.
  • G 1 represents nitrogen or CR 6 ,
  • R 6 represents hydrogen
  • R 1 represents hydrogen, or halogen
  • R 2 represents hydrogen, halogen, or an amino group
  • R 3 represents hydrogen
  • R 4 represents halogen, a nitro group, a cyano group, or a chain C1-C6 hydrocarbon group optionally substituted with halogen.
  • G 1 represents nitrogen or CR 6 .
  • R 6 represents hydrogen
  • R 1 represents hydrogen, or halogen
  • R 2 represents hydrogen, halogen, or an amino group
  • R 3 represents hydrogen
  • R 4 represents halogen, a nitro group, a cyano group, or a chain C1-C6 hydrocarbon group optionally substituted with halogen.
  • the "halogen” includes fluorine, chlorine, bromine and iodine.
  • the "chain C1-C6 hydrocarbon group” includes, for example, C1-C6 alkyl groups such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isopentyl group, 1- methylbutyl group, a tert-pentyl group, a neopentyl group, a hexyl group and an isohexyl group; C2-C6 alkenyl groups such as a vinyl group, a 2-propenyl group, a 2-butenyl group, a 3-butenyl group, a 2-methyl-2- propenyl group, a 3-methyl-2-butenyl group, a 2-pentenyl group and a 2-hexenyl group; and C2-C6 alkyl groups such as
  • the "chain C1-C6 hydrocarbon group optionally substituted with halogen” includes, for example, C1-C6 alkyl groups optionally substituted with halogen, such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isopentyl group, a 1-methylbutyl group, a tert-pentyl group, a neopentyl group, a hexyl group, an isohexyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a 2, 2, 2-trifluoroethyl group, a 2, 2, 2-trichloroethyl group, a pentafluoroethyl group, a perfluor
  • the "phenyl group optionally substituted with one or more members selected from Group A” includes, for example, a phenyl group, a 2-chlorophenyl group, a 3-chlorophenyl group, a 4-chlorophenyl group, a 2- aminophenyl group, a 3-aminophenyl group, a 4-aminophenyl group, a 2-cyanophenyl group, a 3-cyanophenyl group, a 4- cyanophenyl group, a 2-nitrophenyl group, a 3-nitrophenyl group, a 4-nitrophenyl group, a 2-methylphenyl group, a 3- methylphenyl group, a 4-methylphenyl group, a 2- (trifluoromethyl) phenyl group, a 3- (trifluoromethyl) phenyl group, a 4- (trifluoromethyl) phenyl group, a 2-methoxyphenyl group, a 3-methoxypheny
  • the "5- or 6-membered aromatic heterocyclic group” includes, for example, a 2- pyrrolyl group, a 2-furyl group, a 3-furyl group, a 2- thienyl group, a 3-thienyl group, a 5-pyrazolyl group, a 4- pyrazolyl group, a 2-pyridinyl group, a 3-pyridinyl group, a 4-pyridinyl group, a pyrazinyl group, 1-pyrrolyl group and 1-pyrazolyl group.
  • the "5- or 6-membered aromatic heterocyclic group optionally substituted with one or more members selected from Group A” includes, for example, a l-methyl-2-pyrrolyl group, a 2-furyl group, a 3-furyl group, a 5-bromo-2-furyl group, a 5-nitro-2-furyl group, a 2-methyl-3-furyl group, a 2, 5-dimethyl-3-furyl group, a 2,4- dimethyl-3-furyl group, a 2-thienyl group, a 3-thienyl group, a 5-methyl-2-thienyl group, a 3-methyl-2-thienyl group, a 1- methyl-3-trifluoromethyl-5-pyrazolyl group, a 5-chloro-l, 3- dimethyl-4-pyrazolyl group, a 2-pyridinyl group, a 3- pyridinyl group, a 4-pyridinyl group, a 2-methyl-3-pyridinyl
  • the "C1-C6 alkoxy group optionally substituted with halogen” includes, for example, a methoxy group, a trifluoromethoxy group, an ethoxy group, a 2, 2, 2-trifluoroethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, an isobutyloxy group, a sec-butyloxy group, a tert-butyloxy group, a pentyloxy group and a hexyloxy group.
  • the "C1-C6 alkylsulfonyl group optionally substituted with halogen” includes, for example, a methylsulfonyl group, a trifluoromethylsulfonyl group and an ethylsulfonyl group.
  • the "C1-C4 alkylamino group optionally substituted with halogen” includes, for example, a methylamino group, an ethylamino group, a 2,2,2- trifluoroethylamino group, a propylamino group, an isopropylamino group and a butylamino group.
  • the "C2-C8 dialkylamino group optionally substituted with halogen” includes, for example, a dimethylamino group, a diethylamino group, a bis (2,2, 2- trifluoroethyl) amino group and a dipropylamino group.
  • the "C3-C8 cycloalkyl group optionally substituted with halogen” includes, for example, a cyclopropyl group, a 2, 2-difluorocyclopropyl group, a 2,2- dichlorocyclopropyl group, a 2, 2-dibromocyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group and a cyclooctyl group.
  • the "Cl-ClO alkyl group substituted with one or more members selected from Group B” includes, for example, a 2, 2-dichloropropyl group, a 2- chloro-2-methylpropyl group, a 2, 2, 2-trichloroethyl group, a l-methyl-2, 2, 2-trichloroethyl group, a monofluoromethyl group, a difluoromethyl group, a trifluoromethyl group, 1,1- difluoroethyl group, a 2, 2-difluoroethyl group, 1,2,2- trifluoroethyl group, a 2, 2, 2-trifluoroethyl group, a 1, 1, 2, 2-tetrafluoroethyl group, a 1, 1, 2, 2, 2-pentafluoroethyl group, 1-fluoropropyl group, a 2-fluoropropyl group, a 3- fluoropropyl group, 1, 1-difluoropropyl group,
  • the "C3-C10 alkenyl group substituted with one or more members selected from Group B” includes, for example, a 3, 3-dichloro-2-propenyl group, a 2, 3, 3-trichloro-2-propenyl group, a 3, 3-difluoro-2-propenyl group, a 2, 3-difluoro-2-propenyl group, a 4, 4, 4-trifluoro-2- butenyl group, a 2, 3, 4, 4, 4-pentafluoro-2-butenyl group, a 4- methoxy-2-propenyl group, a 4-methylthio-2-propenyl group and a 4-dimethylamino-2-propenyl group.
  • the "C1-C6 alkyl group optionally substituted with halogen” includes, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isopentyl group, a 1- methylbutyl group, a tert-pentyl group, a neopentyl group, a hexyl group, an isohexyl group, a 1, 1, 1-trifluoromethyl group, a 2, 2, 2-trifluoroethyl group and a 2,2,2- trichloroethyl group.
  • Examples of the present compound includes the following pyrimidine compounds.
  • a pyrimidine compound represented by formula (1), wherein R 1 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, -L 1 R 7 or a -C( O)R 8 .
  • a pyrimidine compound represented by formula (1), wherein R 2 is hydrogen, halogen, a nitro group, a cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, -L 1 R 7 or -C( 0)R 8 .
  • a pyrimidine compound represented by formula (1) wherein R 1 is hydrogen, halogen or a chain C1-C6 hydrocarbon group optionally substituted with halogen, R 2 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L 1 R 7 , G 1 is nitrogen or CR 6 , and R 6 is hydrogen.
  • R 1 is hydrogen, R 2 is hydrogen or an amino group, G 1 is nitrogen or CR 6 , and R 6 is hydrogen.
  • a pyrimidine compound represented by formula (1), wherein R 4 is hydrogen, halogen, a nitro group, a cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, or -C( O)R 11 .
  • R 4 is hydrogen, chlorine or a methyl group.
  • a pyrimidine compound represented by formula (1), wherein R 3 is hydrogen, R 4 is hydrogen, halogen, a nitro group, a cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, -L 2 R 10 or -CC O)R 11 .
  • a pyrimidine compound represented by formula (1), wherein R 1 , R 2 and R 6 are the same or different and represent hydrogen, halogen, a nitro group, a cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, -L 1 R 7 or -C( O)R 8 .
  • a pyrimidine compound represented by formula (1), wherein R 1 , R 2 and R 6 are the same or different and represent hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, -L 1 R 7 or -C( O)R 8 .
  • a pyrimidine compound represented by formula (1), wherein R 1 and R 6 are the same or different and represent hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -C( O)R 8 .
  • a pyrimidine compound represented by formula (1) wherein R 1 is hydrogen, halogen, or a chain C1-C6 hydrocarbon group optionally substituted with halogen, R 2 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L 1 R 7 , G 1 is nitrogen or CR 6 , R 6 is hydrogen, R 3 is hydrogen, and R 4 is hydrogen, halogen, A chain C1-C6 hydrocarbon group optionally substituted with halogen, or - L 2 R 10 .
  • a pyrimidine compound represented by formula (1) wherein R 5 is a 3, 3-dichloro-2-propenyl group, a 2, 3, 3-trichloro-2- propenyl group, a 3, 3-difluoro-2-propenyl group, a 4,4,4- trifluoro-2-butenyl group or a 2, 3, 4, 4, 4-pentafluoro-2- butenyl group.
  • R 5 is a 2, 2-dichloropropyl group, a 2-chloro-2-methylpropyl group, a 2, 2, 2-trichloroethyl group, a l-methyl-2, 2, 2- trichloroethyl group, a 2, 2, 3, 3-tetrafluoropropyl group, a
  • G 1 is nitrogen, or CR 6 ,
  • R 1 and R 6 are the same or different and represent hydrogen, halogen, or a chain C1-C6 hydrocarbon group optionally substituted with halogen
  • R 2 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L 1 R 7
  • R 3 is hydrogen or a chain C1-C6 hydrocarbon group optionally substituted with halogen
  • R 4 is hydrogen, halogen, or a chain C1-C6 hydrocarbon group optionally substituted with halogen
  • R 5 is a Cl-ClO alkyl or C3-C10 alkenyl group substituted with halogen or -L 3 R 14 .
  • G 1 is nitrogen or CR 6 ,
  • R 2 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L 1 R 7 ,
  • R 6 is hydrogen
  • R 3 is hydrogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L 2 R 10
  • R 4 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, or -L 2 R 10
  • R 3 is hydrogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L 2 R 10
  • R 4 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, or -L 2 R 10
  • R 5 is a Cl-ClO alkyl group substituted with one or more members selected from Group B, a C3-C10 alkenyl group substituted with or one or more members selected from Group
  • R 1 is hydrogen, halogen, or a chain C1-C6 hydrocarbon group optionally substituted with halogen,
  • R 2 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L 1 R 7 , R 6 is hydrogen,
  • R 3 is hydrogen or a chain C1-C6 hydrocarbon group optionally substituted with halogen
  • R 4 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L 2 R 10 ,
  • R 5 is a Cl-ClO alkyl or C3-C10 alkenyl group substituted with halogen or -L 3 R 14 , and
  • L 3 is oxygen, sulfur or -Si(R 17 ) 2 -•
  • G 1 is a nitrogen or CR 6 ,
  • R 1 is hydrogen, a halogen or a methyl group
  • R 2 is hydrogen, halogen, a methyl group or an amino group
  • R 6 is hydrogen
  • R 3 is hydrogen, aa cchhaaiinn CCll--CC ⁇ hhydrocarbon group optionally substituted with halogen, or -L 2 R 10 , RR 44 iiss hhyyddrrooggeenn,, hhaallooggeenn,, aa cchhaaiinn CCl1--C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, or -L 2 R 10 ,
  • R 5 is a Cl-ClO alkyl or C3-C10 alkenyl group substituted with halogen or -L 3 R 14 , and
  • L 3 is oxygen, sulfur or -Si(R 17 ) 2 -.
  • G 1 is nitrogen or CR 6 , R 1 is hydrogen or halogen, R 2 is hydrogen, halogen, a methyl group or an amino group, R 6 is hydrogen,
  • R 3 is hydrogen or a chain C1-C6 hydrocarbon group optionally substituted with halogen
  • R 4 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L 2 R 10 ,
  • R 5 is a Cl-ClO alkyl or C3-C10 alkenyl group substituted with halogen or -L 3 R 14 , and
  • L 3 is oxygen, sulfur or -Si(R 17 ) 2 --
  • the present compound can be produced, for example, in accordance with the following (Production Process A) to (Production Process E).
  • R 1 , R 2 , R 3 , R 4 , R 5 and G 1 are as defined above, and Q' represents oxygen or sulfur (hereinafter referred to as the present compound (1-i)) can be produced by reacting the compound represented by formula (2) :
  • R 1 , R 2 , R 3 , R 4 and G 1 are as defined above (hereinafter referred to as the compound (2) ) with the compound represented by formula (3) :
  • R 5 -Q'-H wherein R 5 and Q' are as defined above hereinafter referred to as the compound (3) .
  • the reaction is performed in the presence or absence of a solvent.
  • the solvent used in the reaction includes, for example, water; ethers such as 1,4-dioxane, diethylether, tetrahydrofuran and tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane and chlorobenzene; hydrocarbons such as toluene, benzene and xylene; nitriles such as acetonitrile; aprotic polar solvents such as N, N- dimethylformamide, N-methyl pyrrolidone (hereinafter referred to as NMP), 1, 3-dimethyl-2-imidazolidinone and dimethyl sulfoxide; and mixtures thereof.
  • NMP N- dimethylformamide
  • NMP 1, 3-dimethyl-2-imidazolidinone and dimethyl sulfoxide
  • the amount of the compound (3) used in the reaction is usually from 1 to 2 mol per 1 mol of the compound (2) .
  • the reaction is usually performed in the presence of a base.
  • the base used in the reaction includes, for example, nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2, 6-lutidine, 1, 8-diazabicyclo [5, 4, 0] 7-undecene (hereinafter referred to as DBU) and 1,5- diazabicyclo [4 , 3, 0] 5-nonene; tertiary amines such as triethylamine and N, N-diisopropylethylamine; and inorganic bases such as potassium carbonate and sodium hydride.
  • the amount of the base used in the reaction is usually
  • the reaction temperature of the reaction is usually within a range from -20 to 100°C.
  • the reaction time of the reaction is usually within a range from 0.1 to 24 hours.
  • the isolated present compound (1-i) can be isolated by pouring the reaction mixture into water followed by extraction with an organic solvent and subsequent concentration of the organic layer; pouring the reaction mixture into water followed by collection of the formed solid by filtration; or collecting a solid formed in the reaction mixture by filtration.
  • the isolated present compound (1-i) can also be further purified by recrystallization, chromatography and so on.
  • the compound (2) includes, for example, the following pyrimidine compounds .
  • a pyrimidine compound represented by formula (2), wherein R 4 is hydrogen, halogen, a nitro group, a cyano. group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen or -CC O)R 11 .
  • a pyrimidine compound represented by formula (2), wherein R 4 is halogen, a nitro group, a cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3- C8 cycloalkyl group optionally substituted with halogen or - CC O)R 11 .
  • a pyrimidine compound represented by formula (2), wherein R 3 is hydrogen and R 4 is hydrogen, halogen, a nitro group, A cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, -L 2 R 10 or -CC O)R 11 .
  • the present compound (1-i) can be produced by reacting the compound represented by formula (4):
  • R 4 wherein R , R r ⁇ 4 , intentionR5 and Q' are as defined above (hereinafter referred to as the compound (4)) with the compound represented by formula (5) : wherein R 1 , R 2 and G 1 are as defined above (hereinafter referred to as the compound (5)) .
  • the reaction is performed in the presence or absence of a solvent.
  • the solvent used in the reaction includes, for example, water; ethers such as 1,4-dioxane, diethylether, tetrahydrofuran and tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane and chlorobenzene; hydrocarbons such as toluene, benzene and xylene; nitriles such as acetonitrile; aprotic polar solvents such as N, N- dimethylformamide, NMP, 1, 3-dimethyl-2-imidazolidinone and dimethyl sulfoxide; and mixtures thereof.
  • the amount of the compound (5) used in the reaction is usually from 1 to 2 mol per 1 mol of the compound (4) .
  • the reaction is usually performed in the presence of a base .
  • the base used in the reaction includes, for example, nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2, 6-lutidine, DBU and 1, 5-diazabicyclo [4 , 3, 0] 5- nonene; tertiary amines such as triethylamine and N, N- diisopropylethylamine; and inorganic bases such as potassium carbonate and sodium hydride.
  • nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2, 6-lutidine, DBU and 1, 5-diazabicyclo [4 , 3, 0] 5- nonene
  • tertiary amines such as triethylamine and N, N- diisopropylethylamine
  • inorganic bases such as potassium carbonate and sodium hydride.
  • the amount of the base used in the reaction is usually 1 mol or more per 1 mol of the compound (4) .
  • the reaction temperature of the reaction is usually within a range from -20 to 100 0 C.
  • the reaction time of the reaction is usually within a range from 0.1 to 24 hours.
  • the isolated present compound (1-i) can be isolated by pouring the reaction mixture into water followed by extraction with an organic solvent and subsequent concentration of the organic layer; pouring the reaction mixture into water followed by collection of the formed solid by filtration; or collecting a solid formed in the reaction mixture by filtration.
  • the isolated present compound (1-i) can also be further purified by recrystallization, chromatography and so on.
  • the compound (4) includes, for example, the following pyrimidine compounds .
  • a pyrimidine compound represented by formula (4), wherein R 4 is hydrogen, halogen, a nitro group, a cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, or -CC O)R 11 .
  • a pyrimidine compound represented by formula (4), wherein R 3 is hydrogen, R 4 is hydrogen, halogen, a nitro group, a cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, -L 2 R 10 or -CC O)R 11 .
  • R 1 , R 2 , R 3 , R 4 and G 1 are as defined above] (hereinafter referred to as the compound (6)) with the compound (3) .
  • the reaction is performed in the presence or absence of a solvent.
  • the solvent used in the reaction includes, for example, water; ethers such as 1,4-dioxane, diethylether, tetrahydrofuran and tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane and chlorobenzene; hydrocarbons such as toluene, benzene and xylene; nitriles such as acetonitrile; aprotic polar solvents such as N, N- dimethylformamide, NMP, 1, 3-dimethyl-2-imidazolidinone and dimethyl sulfoxide; and mixtures thereof.
  • the amount of the compound (3) used in the reaction is usually from 1 to 2 mol per 1 mol of the compound (6) .
  • the reaction is usually performed in the presence of a base.
  • the base used in the reaction includes, for example, nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2, 6-lutidine, DBU and 1, 5-diazabicyclo [4, 3, 0] 5- nonene; tertiary amines such as triethylamine and N, N- diisopropylethylamine; and inorganic bases such as potassium carbonate and sodium hydride.
  • the amount of the base used in the reaction is usually 1 mol or more per 1 mol of the compound ( 6) .
  • the reaction temperature of the reaction is usually within a range from -20 to 100°C.
  • the reaction time of the reaction is usually within a range from 0.1 to 24 hours.
  • the isolated present compound (1-i) can be isolated by pouring the reaction mixture into water followed by extraction with an organic solvent and subsequent concentration of the organic layer; pouring the reaction mixture into water followed by collection of the formed solid by filtration; or collecting a solid formed in the reaction mixture by filtration.
  • the isolated present compound (1-i) can also be further purified by recrystallization, chromatography and so on.
  • the compound (6) includes, for example, the following pyrimidine compounds .
  • a pyrimidine compound represented by formula (6), wherein R 4 is hydrogen, halogen, a nitro group, a cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, or -CC O)R 11 .
  • a pyrimidine compound represented by formula (6), wherein R 4 is halogen, a nitro group, a cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3- C8 cycloalkyl group optionally substituted with halogen, or -CC O)R 11 .
  • R 4 is hydrogen, halogen, or a chain C1-C6 hydrocarbon group.
  • the present compound (1-i) can be produced by reacting the compound represented by formula (7) :
  • R 1 , R 2 , R 3 , R 4 , G 1 and Q' are as defined above
  • R 5 -L wherein R 5 is as defined above, L represents a leaving group (chlorine, bromine, iodine, a paratoluenesulfonyloxy group, a methanesulfonyloxy group and so on) (hereinafter referred to as the compound (8) ) .
  • the reaction is performed in the presence or absence of a solvent.
  • the solvent used in the reaction includes, for example, water; ethers such as 1,4-dioxane, diethylether, tetrahydrofuran and tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane and chlorobenzene; hydrocarbons such as toluene, benzene and xylene; nitriles such as acetonitrile; aprotic polar solvents such as N, N- dimethylformamide, NMP, 1, 3-dimethyl-2-imidazolidinone and dimethyl sulfoxide; and mixtures thereof.
  • the amount of the compound (8) used in the reaction is usually from 1 to 2 mol per 1 mol of the compound (7) .
  • the reaction is usually performed in the presence of a base.
  • the base used in the reaction includes, for example, nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2, 6-lutidine, DBU and 1, 5-diazabicyclo [4 , 3, 0] 5- nonene; tertiary amines such as triethylamine and N, N- diisopropylethylamine; and inorganic bases such as potassium carbonate and sodium hydride.
  • the amount of the base used in the reaction is usually 1 mol or more per 1 mol of the compound (7 ) .
  • the reaction temperature of the reaction is usually within a range from -20 to 100°C.
  • the reaction time of the reaction is usually within a range from 0.1 to 24 hours.
  • the present compound (1-i) can be isolated by pouring the reaction mixture into water followed by extraction with an organic solvent and subsequent concentration of the organic layer; ; pouring the reaction mixture into water followed by collection of the formed solid by filtration; or collecting a solid formed in the reaction mixture by filtration.
  • the isolated present compound (1-i) can also be further purified by recrystallization, chromatography and so on.
  • the compound (7) includes, for example, the following pyrimidine compounds.
  • a pyrimidine compound represented by formula (7) wherein G 1 is CR 6 , R 6 is hydrogen and R 3 is hydrogen.
  • a pyrimidine compound represented by formula (7), wherein R 4 is hydrogen, halogen, a nitro group, a cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, or -CC O)R 11 .
  • a pyrimidine compound represented by formula (7), wherein R 4 is halogen, a nitro group, a cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3- C8 cycloalkyl group optionally substituted with halogen, or -C C O)R 11 .
  • a pyrimidine compound represented by formula (7), wherein R 3 is hydrogen and R 4 is hydrogen, halogen, a nitro group, A cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, -L 2 R 10 or -CC O)R 11 .
  • R 1 , R 2 , R 3 , R 4 , R 5 and G 1 are as defined above, and Q" represents -S(O)- or -S(O) 2 - (hereinafter referred to as the present compound (1-ii)), the compound represented by formula (1-iii) :
  • R 1 , R 2 , R 3 , R 4 , R 5 and G 1 are as defined above (hereinafter referred to as the compound (1-iii)), and an oxidizing agent.
  • the compound (2) can be produced by reacting the compound represented by formula (9):
  • R 3 and R 4 are as defined above (hereinafter referred to as the compound (9)) with the compound represented by the compound (5) .
  • the reaction is performed in the presence or absence of a solvent.
  • the solvent used in the reaction includes, for example, water; ethers such as 1,4-dioxane, diethylether, tetrahydrofuran and tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane and chlorobenzene; hydrocarbons such as toluene, benzene and xylene; nitriles such as acetonitrile; aprotic polar solvents such as N, N- dimethylformamide, NMP, 1, 3-dimethyl-2-imidazolidinone and dimethyl sulfoxide; and mixtures thereof.
  • the amount of the compound (5) used in the reaction is usually from 1 to 2 mol per 1 mol of the compound (9) .
  • the reaction is usually performed in the presence of a base.
  • the base used in the reaction includes, for example, nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2, 6-lutidine, DBU and 1, 5-diazabicyclo [4, 3, 0] 5- nonene; tertiary amines such as triethylamine and N, N- diisopropylethylamine; and inorganic bases such as potassium carbonate and sodium hydride.
  • the amount of the base used in the reaction is usually 1 mol or more per 1 mol of the compound ( 9) .
  • the reaction temperature of the reaction is usually within a range from -20 to 100°C.
  • the reaction time of the reaction is usually within a range from 0.1 to 24 hours.
  • the present compound (2) can be isolated by pouring the reaction mixture into water followed by extraction with an organic solvent and subsequent concentration of the organic layer; pouring the reaction mixture into water followed by collection of the formed solid by filtration; or collecting a solid formed in the reaction mixture by filtration.
  • the isolated present compound (2) can also be further purified by recrystallization, chromatography and so on.
  • R 3 and R 4 are as defined above (hereinafter referred to as the compound (10)) with the compound represented by formula (11) :
  • R 14 represents a C1-C6 alkyl group optionally- substituted with halogen (hereinafter referred to as the compound (11) ) .
  • the reaction is performed in the presence or absence of a solvent.
  • the solvent used in the reaction includes, for example, water; ethers such as 1,4-dioxane, diethylether, tetrahydrofuran and tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane and chlorobenzene; hydrocarbons such as toluene, benzene and xylene; nitriles such as acetonitrile; aprotic polar compounds such as N, N- dimethylformamide, NMP, 1, 3-dimethyl-2-imidazolidinone and dimethyl sulfoxide; and mixtures thereof.
  • the amount of the compound (11) used in the reaction is usually from 1 to 2 mol per 1 mol of the compound (10) .
  • the reaction temperature of the reaction usually within a range from -20 to 100 0 C.
  • the reaction time of the reaction is usually within a range from 0.1 to 24 hours.
  • the compound (2- i) can be isolated by pouring the reaction mixture into water followed by extraction with an organic solvent and subsequent concentration of the organic layer. The isolated compound (2-i) can further purified by chromatography, distillation and so on.
  • the compound (10) can be produced by reacting the compound (9) with hydrazine.
  • the reaction is performed in the presence or absence of a solvent.
  • the solvent used in the reaction includes, for example, water; ethers such as 1,4-dioxane, diethylether, tetrahydrofuran and tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane and chlorobenzene; hydrocarbons such as toluene, benzene and xylene; nitriles such as acetonitrile; aprotic polar compounds such as N, N- dimethylformamide, NMP, 1, 3-dimethyl-2-imidazolidinone and dimethyl sulfoxide; and mixtures thereof.
  • the hydrazine used in the reaction includes, for example, hydrazine and hydrazine hydrate.
  • the amount of the hydrazine used in the reaction is usually from 1 to 10 mol per 1 mol of the compound (9) .
  • the reaction is usually performed in the presence of a base.
  • the base used in the reaction includes, for example, nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2, 6-lutidine, DBU and 1, 5-diazabicyclo [4 , 3, 0] 5- nonene; tertiary amines such as triethylamine and N, N- diisopropylethylamine; and inorganic bases such as potassium carbonate and sodium hydride.
  • the amount of the base used in the reaction is usually 1 mol or more per 1 mol of the compound (9) .
  • the reaction temperature of the reaction is usually within a range from 0 to 100°C.
  • the reaction time of the reaction is usually within a range from 0.1 to 24 hours.
  • the compound (10) can be isolated by pouring the reaction, mixture into water followed by extraction with an organic solvent and subsequent concentration of the organic layer; pouring the reaction mixture into water followed by collection of the formed solid by filtration; or collecting a solid formed in the reaction mixture by filtration.
  • the isolated compound (10) can further purified by chromatography, distillation and so on.
  • the compound (4) can be produced by reacting the compound (9) with the compound (3) .
  • the reaction is performed in the presence or absence of a solvent.
  • the solvent used in the reaction includes, for example, water; ethers such as 1,4-dioxane, diethylether, tetrahydrofuran and tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane and chlorobenzene; hydrocarbons such as toluene, benzene and xylene; nitriles such as acetonitrile; aprotic polar solvents such as N, N- dimethylformamide, NMP, 1, 3-dimethyl-2-imidazolidinone and dimethyl sulfoxide; and mixtures thereof.
  • the amount of the compound (3) used in the reaction is usually from 1 to 2 mol per 1 mol of the compound (9) .
  • the reaction is usually performed in the presence of a base.
  • the base used in the reaction includes, for example, nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2, 6-lutidine, DBU and 1, 5-diazabicyclo [4, 3, 0] 5- nonene; tertiary amines such as triethylamine and N, N- diisopropylethylamine; and inorganic bases such as potassium carbonate and sodium hydride.
  • the amount of the base used in the reaction is usually 1 mol or more per 1 mol of the compound ( 9 ) .
  • the reaction temperature of the reaction is usually within a range from 0 to 100°C.
  • the reaction time of the reaction is usually within a range from 0.1 to 24 hours.
  • the present compound (4) can be isolated by pouring the reaction mixture into water followed by extraction with an organic solvent and subsequent concentration of the organic layer; pouring the reaction mixture into water followed by collection of the formed solid by filtration; or collecting a solid formed in the reaction mixture by filtration.
  • the isolated present compound (4) can also be further purified by recrystallization, chromatography and so on.
  • the compound (6) can be produced by reacting the compound (9) with the compound (5).
  • the reaction is performed in the presence or absence of a solvent.
  • the solvent used in the reaction includes, for example, water; ethers such as 1,4-dioxane, diethylether, tetrahydrofuran and tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane and chlorobenzene; hydrocarbons such as toluene, benzene and xylene; nitriles such as acetonitrile; aprotic polar solvents such as N, N- dimethylformamide, NMP, 1, 3-dimethyl-2-imidazolidinone and dimethyl sulfoxide; and mixtures thereof.
  • the amount of the compound (5) used in the reaction is usually from 2 to 3 mol per 1 mol of the compound (9) .
  • the reaction is usually performed in the presence of a base.
  • the base used in the reaction includes, for example, nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2, 6-lutidine, DBU and 1, 5-diazabicyclo [4 , 3, 0] 5- nonene; tertiary amines such as triethylamine and N, N- diisopropylethylamine; and inorganic bases such as potassium carbonate and sodium hydride.
  • the amount of the base used in the reaction is usually 2 mol or more per 1 mol of the compound (9) .
  • the reaction temperature of the reaction is usually within a range from 0 to 100°C.
  • the reaction time of the reaction is usually within a range from 0.1 to 24 hours.
  • the present compound (6) can be isolated by pouring the reaction mixture into water followed by extraction with an organic solvent and subsequent concentration of the organic layer; pouring the reaction mixture into water followed by collection of the formed solid by filtration; or collecting a solid formed in the reaction mixture by filtration.
  • the isolated present compound (6) can also be further purified by recrystallization, chromatography and so on.
  • R 1 , R 2 , R 3 , R 4 and G 1 are as defined above
  • the compound (7-i) can be produced, for example, by subjecting the compound represented by formula (Y) :
  • R 1 , R 2 , R 3 , R 4 and G 1 are as defined above, to a hydrolysis reaction.
  • the reaction is usually performed in the presence of a base or an acid in water.
  • An organic solvent may be added to the reaction.
  • the organic solvent includes, for example, ethers such as 1,4-dioxane, diethylether, tetrahydrofuran, tert-butyl methyl ether and diglyme; hydrocarbons such as toluene, benzene and xylene; and nitriles such as acetonitrile.
  • the base used in the reaction includes, for example, inorganic bases such as potassium carbonate, sodium hydroxide, potassium hydroxide and sodium hydride; nitrogen- containing heterocyclic compounds such as pyridine, picoline, 2, 6-lutidine, DBU and 1, 5-diazabicyclo [4, 3, 0] 5-nonene; and tertiary amines such as triethylamine and N, N- diisopropylethylamine.
  • the amount of the based used in the reaction is usually from 0.1 to 4 mol per 1 mol of the compound ( 6) .
  • the acid used in the reaction includes, for example, inorganic acids such as hydrochloric acid, bromic acid and sulfuric acid; and organic acids such as acetic acid and paratoluenesulfonic acid.
  • inorganic acids such as hydrochloric acid, bromic acid and sulfuric acid
  • organic acids such as acetic acid and paratoluenesulfonic acid.
  • the reaction temperature of the reaction is usually within a range from 20 to 120°C.
  • the reaction time of the reaction is usually within a range from 0.1 to 24 hours.
  • the compound (7) can be isolated by pouring the reaction mixture into water followed by extraction with an organic solvent and subsequent concentration of the organic layer; pouring the reaction mixture into water followed by collection of the formed solid by filtration; or collecting a solid formed in the reaction mixture by filtration.
  • the isolated compound (7) can further purified by chromatography, distillation and so on.
  • R 1 , R 2 , R 3 , R 4 and G 1 are as defined above (hereinafter referred to as the compound (7-ii) ) can be produced by reacting the compound (7-i) with a sulfuration agent .
  • the reaction is performed in the presence or absence of a solvent.
  • the solvent used in the reaction includes, for example, ethers such as 1,4-dioxane, diethylether, tetrahydrofuran, tert-butyl methyl ether and diglyme; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane and chlorobenzene; hydrocarbons such as toluene, benzene and xylene; nitriles such as acetonitrile; pyridines such as pyridine, picoline and lutidine; and mixtures thereof.
  • ethers such as 1,4-dioxane, diethylether, tetrahydrofuran, tert-butyl methyl ether and diglyme
  • halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,
  • the sulfuration agent used in the reaction includes, for example, diphosphorus pentasulfide and Lawesson's reagent (2, 4-bis (4-methoxyphenyl) -1, 3-dithia-2, 4- diphosphetane 2, 4-disulfide) .
  • the amount of the sulfuration agent used in the reaction is usually 1 mol or more per 1 mol of the compound (7-i) .
  • the reaction temperature of the reaction is usually within a range from 0 0 C to 200 0 C.
  • the reaction time of the reaction is usually within a range from 1 to 24 hours.
  • the present compound (7-ii) can be isolated by pouring the reaction mixture into water followed by extraction with an organic solvent and subsequent concentration of the organic layer; or collecting a solid formed in the reaction mixture by filtration.
  • the isolated present compound (7-ii) can also be further purified by recrystallization, chromatography and so on.
  • R 1 and R 3 represent hydrogen, Q represents oxygen, and R 2 , R 5 , G 1 and R 6 represent combinations described in Table 1 to Table 6.
  • R 1 and R 3 represent hydrogen
  • Q represents oxygen
  • R 2 , R 5 , G 1 and R 6 represent any one of the combinations described in Table 1 to Table 6.
  • R 1 and R 3 represent hydrogen
  • Q represents oxygen
  • R 2 , R 5 , G 1 and R 6 represent any one of the combinations described in Table 1 to Table 6.
  • a compound represented by formula (E) wherein R 1 and R 3 represent hydrogen, Q represents oxygen, and R 2 , R 5 , G 1 and R 6 represent any one of the combinations described in Table 1 to Table 6.
  • R 1 and R 3 represent hydrogen
  • Q represents oxygen
  • R 2 , R 5 , G 1 and R 6 represent any one of the combinations described in Table 1 to Table 6.
  • R 1 and R 3 represent hydrogen
  • Q represents oxygen
  • R 2 , R 5 , G 1 and R 6 represent any one of the combinations described in Table 1 to Table 6.
  • a compound represented by formula (H) wherein R 1 and R 3 represent hydrogen, Q represents sulfur, and R 2 , R 5 , G 1 and R 6 represent any one of the combinations described in Table 1 to Table 6.
  • R 1 and R 3 represent hydrogen
  • Q represents sulfur
  • R 2 , R 5 , G 1 and R 6 represent any one of the combinations described in Table 1 to Table 6.
  • R 1 and R 3 represent hydrogen
  • Q represents sulfur
  • R 2 , R 5 , G 1 and R 6 represent any one of the combinations described in Table 1 to Table 6.
  • Pests against which the present compound has an activity include, for example, noxious arthropods such as noxious insects and noxious acarines, and nematodes. Specific examples of these pests include the following.
  • Planthoppers such as small brown planthopper (Laodelphax striatellus) , brown rice planthopper (Nilaparvata lugens), and white-backed rice planthopper (Sogatella furcifera) ; leafhoppers (Deltocephalidae) such as green rice leafhopper (Nephotettix cincticeps) , green rice leafhopper (Nephotettix virescens) , and tea green leafhopper (Empoasca onukii) ; aphids (Aphididae) such as cotton aphid (Aphis gossypii) , green peach aphid (Myzus persicae) , cabbage aphid (Brevicoryne brassicae) , piraea aphid (Aphis spiraecola) , potato aphid (Macrosiphum euphorbiae
  • Pyralid moths such as rice stem borer (Chilo suppressalis) , yellow rice borer (Tryporyza incertulas) , rice leafroller (Cnaphalocrocis medinalis) , cotton leafroller (Notarcha derogata) , Indian meal moth
  • Noctuidae such as common cutworm (Spodoptera litura) , beet armyworm (Spodoptera exigua) , armyworm (Pseudaletia separata) , cabbage armyworm (Mamestra brassicae) , black cutworm • (Agrotis ipsilon) , beet semi-looper (Plusia nigrisigna) , Thoricoplusia spp., Heliothis spp., and Helicoverpa spp.; white butterflies (Pieridae) such as common white (Pieris rapae) ; tortricid moths (Tortricidae) such as Adoxophyes spp., oriental fruit moth (Grapholita molesta) , soybean pod borer (Leguminivora glycinivorella) , azuki bean podworm (Matsumuraeses azukivora) , summer fruit tortrix (Adoxophyes or
  • Hybridae such as pink bollworm (Pectinophora gossypiella) , and potato tubeworm (Phthorimaea operculella) ; tiger moths and allies (Arctiidae) such as fall webworm
  • tineid moths such as casemaking clothes moth (Tinea translucens) , and webbing clothes moth (Tineola bisselliella) .
  • Thysanoptera
  • Thrips such as yellow citrus thrips (Frankliniella occidentalis) , melon thrips (Thrips palmi) , yellow tea thrips (Scirtothrips dorsalis) , onion thrips (Thrips tabaci) , flower thrips (Frankliniella intonsa) .
  • Diptera Culices such as common mosquito (Culex pipiens pallens) , Cluex tritaeniorhynchus, and Cluex quinquefasciatus; Aedes spp. such as yellow fever mosquito (Aedes aegypti) , and Asian tiger mosquito (Aedes albopictus) ; Anopheles spp.
  • Leafminer flies such as rice leafminer (Agromyza oryzae) , little rice leafminer (Hydrellia griseola) , tomato leafminer (Liriomyza sativae) , legume leafminer (Liriomyza trifolii) , and garden pea leafminer (Chromatomyia horticola) ;
  • Corn root worms such as Western corn root worm (Diabrotica virgifera virgifera) , and Sourthern corn root worm (Diabrotica undecimpunctata howardi) ; scarabs (Scarabaeidae) such as cupreous chafer (Anomala cuprea) , soybean beetle (Anomala rufocuprea) , and Japanese beetle (Popillia japonica); weevils such as maize weevil (Sitophilus zeamais) , rice water weevil (Lissorhoptrus oryzophilus) , azuki bean weevil (Callosobruchus chinensis), rice curculio (Echinocnemus squameus) , boll weevil (Anthonomus grandis) , and hunting billbug (Sphenophorus venatus) ; darkling beetles (Tene
  • Asiatic locust (Locusta migratoria) , African mole cricket (Gryllotalpa africana) , rice grasshopper (Oxya yezoensis) , rice grasshopper (Oxya japonica) , Gryllidae.
  • Ants such as pharaoh ant (Monomorium pharaosis) , negro ant (Formica fusca japonica), black house ant (Ochetellus glaber) , Pristomyrmex ponnes, Pheidole noda, leaf-cutting ant (Acromyrmex spp.) / and fire ant (Solenopsis spp.); hornets (Vespidae) ; bethylid wasps (Betylidae) ; sawflies (Tenthredinidae) such as cabbage sawfly (Athalia rosae) , and Athalia japonica.
  • Aphelenchoides besseyi, Nothotylenchus acris, Meloidogyne incognita, Meloidogyne hapla, Meloidogyne javanica, Heterodera glycines, Globodera rostochiensis, Pratylenchus coffeae, Pratylenchus neglectus .
  • Blattodea German cockroach (Blattella germanica) , smokybrown cockroach (Periplaneta fuliginosa) , American cockroach (Periplaneta americana) , Periplaneta brunnea, oriental cockroach (Blatta orientalis) ;
  • Spider mites such as two-spotted spider mite (Tetranychus urticae) , Kanzawa spider mite (Tetranychus kanzawai) , citrus red mite (Panonychus citri) , European red mite (Panonychus ulmi) , and Oligonychus spp.; eriophyid mites (Eriophyidae) such as pink citrus rust mite (Aculops pelekassi) , Phyllocoptruta citri, tomato rust mite (Aculops lycopersici) , purple tea mite (Calacarus carinatus), pink tea rust mite (Acaphylla theavagran) , Eriophyes chibaensis, and apple rust mite (Aculus Mattendali) ; tarosonemid mites (Tarsonemidae) such as broad mite (Polyphagotars
  • the pest controlling agent of the present invention contains the present compound and an inert carrier.
  • the pest controlling agent of the present invention is a formulation obtained by mixing the present compound and an inert carrier such as a solid carrier, a liquid carrier and a gaseous carrier, and further adding a surfactant and other adjuvant for formulation, if necessary.
  • the formulation includes, for example, an emulsion, an oil solution, a powder, a granule, a wettable powder, a flowable formulation, a microcapsule, an aerosol, a smoking agent, a poison bait, and a resin formulation.
  • the present compound is usually contained in an amount of 0.01% to 95% by weight.
  • the solid carrier used for formulation includes, for example, a fine power and a granule of clays (e.g., kaolin clay, diatomite, bentonite, Fubasami clay, and acid clay) , synthetic hydrated silicon oxide, talc, ceramic, other inorganic minerals (e.g., sericite, quartz, sulfur, activated carbon, calcium carbonate, hydrated silica) or chemical fertilizers (e.g., ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, and ammonium chloride) .
  • clays e.g., kaolin clay, diatomite, bentonite, Fubasami clay, and acid clay
  • synthetic hydrated silicon oxide talc
  • ceramic other inorganic minerals
  • other inorganic minerals e.g., sericite, quartz, sulfur, activated carbon, calcium carbonate, hydrated silica
  • chemical fertilizers e.g., ammonium sulfate,
  • the liquid carrier includes, for example, water, alcohols (e.g., methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, phenoxyethanol) , ketones (e.g., acetone, methyl ethyl ketone, cyclohexanone) , aromatic hydrocarbons (e.g., toluene, xylene, ethylbenzene, dodecylbenzene, phenylxylylethane, methylnaphthalene) , aliphatic hydrocarbons (e.g., hexane, cyclohexane, kerosine, light oil), esters (e.g., ethyl acetate, butyl acetate, isopropyl mylistate, ethyl oleate, diisopropyl adipate, diisobut
  • the gaseous carrier includes, for example, fluorocarbons, butane gas, liquefied petroleum gas (LPG) , dimethyl ether, and carbon dioxide.
  • fluorocarbons for example, fluorocarbons, butane gas, liquefied petroleum gas (LPG) , dimethyl ether, and carbon dioxide.
  • LPG liquefied petroleum gas
  • the surfactant includes, for example, nonionic surfactant, such as polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyethyleneglycol fatty acid ester; and anionic surfactant, such as alkylsulfonic acid salts, alkylbenzenesulfonic acid salts, alkylsurfic acid salts.
  • nonionic surfactant such as polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyethyleneglycol fatty acid ester
  • anionic surfactant such as alkylsulfonic acid salts, alkylbenzenesulfonic acid salts, alkylsurfic acid salts.
  • the other adjuvant for formulation includes, for example, binders, dispersants, colorants and stabilizers, and specifically for example, casein, gelatin, polysaccharides (e.g., starch, gum arabic, cellulose derivatives, alginic acid) , lignin derivatives, synthetic water-soluble polymers (e.g., polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acid), PAP (isopropyl acid phosphate), BHT (2, 6-di-t-butyl-4-methylphenol) , BHA (a mixture of 2-t-butyl-4-methoxyphenol and 3-t-butyl-4- methoxyphenol) .
  • binders e.g., dispersants, colorants and stabilizers
  • casein e.g., gelatin, polysaccharides (e.g., starch, gum arabic, cellulose derivatives, alginic acid) , lignin derivatives, synthetic water-soluble polymers
  • the method for controlling pests of the present invention is applying an effective amount of the present compound to pests directly and/or habitats of pests (e.g., plant, soil, indoor, and in-body of animals) .
  • the present compound is usually used as the pest controlling agent of the present invention for the method for controlling pests of the present invention.
  • the application amount is usually 1 to 10,000 g as the present compound per 10,000 m 2 .
  • the pest controlling agent of the present invention is a formulation of emulsions, wettable powders or flowables, they are usually applied after a dilution with water to have an active ingredient concentration of 0.01 to 10,000 ppm.
  • the pest controlling agent of the present invention is a formulation of granules or powders, they are usually applied as such.
  • formulations and the dilute aqueous solution of the formulation may be sprayed directly to the plant to be protected from pests, and may be applied to the soil to control the pests living in a soil.
  • the resin formulations of sheets or strip form can be applied by a method such as winding around plants, stretching in the vicinity of plants and laying on the soil surface at the plant bottom.
  • the application amount is usually 0.01 to 1,000 mg as the present compound per 1 m 2 in case of application for plane surface, and 0.01 to 500 mg as the present compound per 1 m 3 in case of application for space.
  • the pest controlling agent of the present invention is a formulation of emulsions, wettable powders or flowables, they are usually applied after a dilution with water to have an active ingredient concentration of 0.01 to 100,000 ppm.
  • the pest controlling agent of the present invention is a formulation of oil solutions, aerosols, smoking agents and poison baits, they are usually applied as such.
  • the pest controlling agent of the present invention could be used in farmlands on which "crops" shown below are cultivated.
  • Agricultural crops corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, sarrazin, sugar beet, rapeseed, sunflower, sugar cane, tobacco;
  • Vegetables Solanaceae vegetables (eggplant, tomato, green pepper, hot pepper, and potato) , Cucurbitaceae vegetables (cucumber, pumpkin, zucchini, watermelon, and melon ) , Cruciferae vegetables (Japanese radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, brown mustard, broccoli, and cauliflower) , Compositae vegetables (burdock, garland chrysanthemum, artichoke, and lettuce) , Liliaceae vegetables (Welsh onion, onion, garlic, and asparagus ) , Umbelliferae vegetables (carrot, parsley, celery, and parsnip), Chenopodiaceae vegetables (spinach, and Swiss chard) , Labiatae vegetables (Japanese basil, mint, and basil) , strawberry, sweat potato, yam, aroid;
  • Fruit trees pomaceous fruits (apple, common pear, Japanese pear, Chinese quince, and quince) , stone fleshy fruits (peach, plum, nectarine, Japanese plum, cherry, apricot, and prune) , citrus plants (Satsuma mandarin, orange, lemon, lime, and grapefruit) , nuts (chestnut, walnut, hazel nut, almond, pistachio, cashew nut, and macadamia nut) , berry fruits (blueberry, cranberry, blackberry, and raspberry) , grape, persimmon, olive, loquat, banana, coffee, date, coconut palm, and oil palm;
  • Trees other fruit trees tea, mulberry, flowering trees (azalea, japonica, hydrangea, sasanqua, lllicium anisatum, cherry tree, tulip poplar, crepe myetle, and orange osmanthus), street trees (ash tree, birch, dogwood, eucalyptus, ginkgo, lilac, maple tree, oak, poplar, cercis, Chinese sweet gum, plane tree, zelkova, Japanese arborvitae, fir tree, Japanese hemlock, needle juniper, pine, spruce, yew, elm, and horse-chestnut) , sweet viburnum, Podocarpus macrophyllus, Japanese cedar, Japanese cypress, croton, spindle tree, Chainese howthorn.
  • flowering trees azalea, japonica, hydrangea, sasanqua, lllicium anisatum, cherry tree, tul
  • Lawn zoysia (Japanese lawn grass, mascarene grass) , Bermuda grass (Cynodon dactylon) , bent grass (creeping bent grass, Agrostis stolonifera, Agrostis tenuis) , bluegrass (Kentucky bluegrass, rough bluegrass) , fescue (tall fescue, chewing fescue, creeping fescue) , ryegrass (darnel, perennial ryegrass) , cocksfoot, timothy grass;
  • flowers (rose, carnation, chrysanthemum, Eustoma grandiflorum Shinners (prairie gentian) , gypsophila, gerbera, pot marigold, salvia, petunia, verbena, tulip, aster, gentian, lily, pansy, cyclamen, orchid, lily of the valley, lavender, stock, ornamental kale, primula, poinsttia, gladiolus, cattleya, daisy, verbena, cymbidium, begonia) , biofuel plants (Jatropha, curcas, safflower, Camelina alyssum, switchgrass, miscanthus, reed canary grass, Arundo donax, kenaf, cassava, willow, algae), foliage plant.
  • flowers rose, carnation, chrysanthemum, Eustoma grandiflorum Shinners (prairie gentian
  • the "crops” include genetically modified crops.
  • the pest controlling agents of the present invention can be a admixture with or together with other insecticides, acaricides, nematocides, fungicides, plant growth regulators, herbicides, and synergists.
  • Organic phosphorus compounds Acephate, Aluminium phosphide, butathiofos, cadusafos, chlorethoxyfos, chlorfenvinphos, chlorpyrifos, chlorpyrifos- methyl, cyanophos: CYAP, diazinon, DCIP (dichlorodiisopropyl ether), dichlofenthion: ECP, dichlorvos (DDVP), dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, etrimfos, fenthion: MPP, fenitrothion: MEP, fosthiazate, formothion, hydrogen phosphide, isofenphos, isoxathion, malathion, mesulfenfos, methidathion: DMTP, monocrotophos, naled: BRP, oxydeprofos: ESP, parathion
  • Carbamate compounds Alanycarb, bendiocarb, benfuracarb, BPMC, carbaryl, carbofuran, carbosulfan, cloethocarb, ethiofencarb, fenobucarb, fenothiocarb, fenoxycarb, furathiocarb, isoprocarb: MIPC, metolcarb, methomyl, methiocarb, NAC, oxamyl, pirimicarb, propoxur: PHC, XMC, thiodicarb, xylylcarb, aldicarb; (3) Pyrethroid compounds:
  • Chlorfluazuron bistrifluron, diafenthiuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, triazuron;
  • Bt toxins Live spores derived from and crystal toxins produced from Bacillus thuringiesis and a mixture thereof;
  • Machine oil nicotine-sulfate; avermectin-B, bromopropylate, buprofezin, chlorphenapyr, cyantraniliprole, cyromazine, D-D (1, 3-Dichloropropene, emamectin-benzoate, fenazaquin, flupyrazofos, hydroprene, methoprene, indoxacarb, metoxadiazone, milbemycin-A, pymetrozine, pyridalyl, pyriproxyfen, spinosad, sulfluramid, tolfenpyrad, triazamate, flubendiamide, lepimectin, Arsenic acid, benclothiaz, Calcium cyanamide, Calcium polysulfide, chlordane, DDT, DSP, flufenerim, flonicamid, flurimfen, formetanate, metam- ammonium, metam-sodium, Me
  • R 100 represents chlorine, bromine or a trifluoromethyl group
  • R 200 represents chlorine, bromine or a methyl group
  • R 300 represents chlorine, bromine or a cyano group and, any compound represented by the following formula (L) :
  • R 1000 represents chlorine, bromine or iodide.
  • Active ingredients of the nematocides DCIP, fosthiazate, levamisol, methyisothiocyanate, morantel tartarate, imicyafos.
  • Azole fungicidal compounds such as propiconazole, prothioconazole, triadimenol, prochloraz, penconazole, tebuconazole, flusilazole, diniconazole, bromuconazole, epoxiconazole, difenoconazole, cyproconazole, metconazole, triflumizole, tetraconazole, myclobutanil, fenbuconazole, hexaconazole, fluquinconazole, triticonazole, bitertanol, imazalil, and flutriafol;
  • Cyclic amine fungicidal compouds such as fenpropimorph, tridemorph, and fenpropidin;
  • Benzimidazole fungicidal compounds such as carbendezim, benomyl, thiabendazole, and thiophanate-methyl; Procymidone; cyprodinil; pyrimethanil; diethofencarb; thiuram; fluazinam; mancozeb; iprodione; vinclozolin; chlorothalonil; captan; mepanipyrim; fenpiclonil; fludioxonil; dichlofluanid; folpet; kresoxim-methyl; azoxystrobin; trifloxystrobin; fluoxastrobin; picoxystrobin; pyraclostrobin; dimoxystrobin; pyribencarb; spiroxamine; quinoxyfen; fenhexamid; famoxadone; fenamidone; zoxamide; ethaboxam; amisulbrom; iprovalicarb; benthi
  • Phenoxyfatty acid herbicidal compounds 2,4-PA, MCP, MCPB, phenothiol, mecoprop, fluroxypyr, triclopyr, clomeprop, and naproanilide Phenoxyfatty acid herbicidal compounds 2,4-PA, MCP, MCPB, phenothiol, mecoprop, fluroxypyr, triclopyr, clomeprop, and naproanilide .
  • Triazine herbicidal compounds atrazine, ametoryn, cyanazine, simazine, propazine, simetryn, dimethametryn, prometryn, metribuzin, indaziflam, and triaziflam.
  • Dinitroaniline herbicidal compounds pendimethalin, prodiamine, and trifluralin.
  • Organic phosphorus herbicidal compounds amiprofos-methyl, butamifos, bensulide, piperophos, anilofos, glyphosate, glufosinate, and bialaphos.
  • Acid amide herbicidal compounds propanil, propyzamide, bromobutide, and etobenzanid.
  • Chloroacetanilide herbicidal compounds acetochlor, alachlor, butachlor, dimethenamid, propachlor, metazachlor, metolachlor, pretilachlor, thenylchlor, and pethoxamid.
  • Diphenylether herbicidal compounds acifluorfen-sodium, bifenox, oxyfluorfen, lactofen, fomesafen, chlomethoxynil, and aclonifen.
  • Cyclic imide herbicidal compounds oxadiazon, cinidon-ethyl, carfentrazone-ethyl, surfentrazone, flumiclorac-pentyl, flumioxazin, pyraflufen- ethyl, oxadiargyl, pentoxazone, fluthiacet-methyl, butafenacil, benzfendizone, and saflufenacil .
  • Triketone herbicidal compounds isoxaflutole, benzobicyclon, sulcotrione, mesotrione, tembotrione, and tefuryltrione.
  • Aryloxyphenoxypropionic acid herbicidal compounds clodinafop-propargyl, cyhalofop-butyl, diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl, and quizalofop-ethyl and metamifol.
  • Trioneoxime herbicidal compounds alloxydim-sodium, sethoxydim, butroxydim, clethodim, cloproxydim, cycloxydim, tepraloxydim, tralkoxydim, and profoxydim.
  • Sulfonylurea herbicidal compounds chlorsulfuron, sulfometuron-methyl, metsulfuron-methyl, chlorimuron-ethyl, tribenuron-methyl, triasulfuron, bensulfuron-methyl, thifensulfuron-methyl, pyrazosulfuron- ethyl, primisulfuron-methyl, nicosulfuron, amidosulfuron, cinosulfuron, imazosulfuron, rimsulfuron, halosulfuron- methyl, prosulfuron, ethametsulfuron-methyl, triflusulfuron- methyl, flazasulfuron, cyclosulfamuron, flupyrsulfuron, sulfosulfuron, azimsulfuron, ethoxysulfuron, oxasulfuron, iodosulfuron-methyl-sodium, foramsul
  • Sulfonamide herbicidal compounds flumetsulam, metosulam, diclosulam, florasulam, cloransulam-methyl, penoxsulam, and pyroxsulam.
  • Compound 91 can be also produced by the following method.
  • 1, 2, 4-triazol sodium salt was added under ice cooling. The mixture was stirred at room temperature for 3 hours, at 50 0 C for 5 hours the 130 0 C for 7 hours. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure.
  • Compound 22 can be also produced by the following method. To the mixture of 0.36 g of 4-chloro-6- ( [1, 2, 4] triazol- 1-yl) -pyrimidine, 0.24 g of 2, 2, 3, 3-tetrafluoropropanol and 4 mL NMP, 0.37 g of DBU was added. The mixture was stirred at room temperature for 30 minutes. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure.
  • R 1 , R 2 , R 3 , R 4 , R 5 , G 1 , R 6 and Q represent combinations described Table 7 to Table 14 shown below.

Abstract

A pyrimidine compound represented by formula (1) has a control effect against pests and is useful as an active ingredient of a pest controlling agent.

Description

DESCRIPTION PYRIMIDINE COMPOUND AND ITS USE FOR PEST CONTROL
Technical Field The present invention relates to a pyrimidine compound and its use in pest control.
Background Art
Compounds having control activity against pests have been found and developed as an active ingredient of a pest controlling agent. Certain pyrimidine compounds are known in, for example, US 2009/005403 Al, JP-A-63-039875, WO 99/41253, US 2008/132522 Al and WO 2005/019207.
Disclosure of the Invention
An object of the present invention is to provide a novel compound having a control activity against pests.
The present inventors have studied so as to find a compound having a control activity against pests and found that a pyrimidine compound represented by the following formula (1) has a control activity against pests, thus leading to the present invention.
That is, the present invention provides the following. [1] A pyrimidine compound represented by formula (1) :
Figure imgf000002_0001
wherein
Q represents oxygen or -S(O)n-, n represents 0, 1 or 2, G1 represents nitrogen or CR6 , R1 , R2 and R6 are the same or different and represent hydrogen, halogen, a nitro group, a cyano group, a chain Cl- C6 hydrocarbon group optionally substituted with halogen, - L1R7, -C(=O)R8, a phenyl group optionally substituted with one or more members selected from Group A, or a 5- or 6- aromatic heterocyclic group optionally substituted with one or more members selected from Group A, L1 represents oxygen, -S(O)n- or -NR9-,
R7 represents hydrogen or a chain C1-C6 hydrocarbon group optionally substituted with halogen, provided that R7 is not hydrogen when L1 is -S(O)n- and n is 1 or 2,
R8 represents hydrogen, a hydroxy group, an amino group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C1-C6 alkoxy group optionally substituted with halogen, a C1-C4 alkylamino group optionally substituted with halogen, or a C2-C8 dialkylamino group optionally substituted with halogen,
R9 represents hydrogen, a chain Cl-Cβ hydrocarbon group optionally substituted with halogen or a C1-C6 alkylsulfonyl group optionally substituted with halogen, R3 represents hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, or - L2 R1 ° , R4 represents hydrogen, halogen, a nitro group, a cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, -L2R10, -CC=O)R11, a phenyl group optionally substituted with one or more members selected from Group A, or a 5- or β-membered aromatic heterocyclic group optionally substituted with one or more members selected from Group A,
L2 represents oxygen, -S(O)n- or -NR12-,
R10 represents hydrogen or a chain C1-C6 hydrocarbon group optionally substituted with halogen, provided that R10 is not hydrogen when L2 is -S(O)n- and n is 1 or 2, R11 represents hydrogen, a hydroxy group, an amino group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C1-C6 alkoxy group optionally substituted with halogen, a C1-C4 alkylamino group optionally substituted with halogen, or a C2-C8 dialkylamino group optionally substituted with halogen,
R12 represents hydrogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or a C1-C6 alkylsulfonyl group optionally substituted with halogen,
R5 represents a Cl-ClO alkyl group substituted with one or more members selected from Group B, or a C3-C10 alkenyl group substituted with or one or more members selected from Group B, Group A represents the group consisting of halogen, an amino group, a cyano group, a nitro group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a Cl- C6 alkoxy group optionally substituted with halogen, and S(0)nR13, in which R13 represents a C1-C6 alkyl group optionally substituted with halogen,
Group B represents the group consisting of halogen, -L3R14 and -C(=O)R15 , wherein L3 represents oxygen, -S(O)n-, -NR16- or -Si(R17 )2~, R14 represents hydrogen, or a chain C1-C6 hydrocarbon group optionally substituted with halogen, provided that R14 is not hydrogen when L3 is -S(O)n- and n is 1 or 2, R15 represents hydrogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C1-C4 alkylamino group optionally substituted with halogen, a C2-C8 dialkylamino group optionally substituted with halogen, or a C1-C6 alkoxy group optionally substituted with halogen, R16 represents hydrogen, or a chain C1-C6 hydrocarbon group optionally substituted with halogen, R17S are the same or different and represents a chain C1-C6 hydrocarbon group optionally substituted with halogen (hereinafter referred to as the present compound) . [2] The pyrimidine compound according to [1] , wherein R1 , R2 and R6 are the same or different and represent hydrogen, halogen, a nitro group, a cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, -L1R7 or -C(=O)R8 ;
[3] The pyrimidine compound according to [1] or [2], wherein R1 , R2 and R6 are the same or different and represent hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, -L1R7 or -C(=O)R8; [4] The pyrimidine compound according to any one of [1] to [3], wherein R1 and R6 are the same or different and represent hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -C(=O)R8; [5] The pyrimidine compound according to any one of [1] to [4], wherein R2 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L1 R7 ;
[6] The pyrimidine compound according to any one of [1] to [5] , wherein R4 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3- C8 cycloalkyl group optionally substituted with halogen, or -L2R10;
[7] The pyrimidine compound according to any one of [1] to [6], wherein R3 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or a C3-C8 cycloalkyl group optionally substituted with halogen;
[8] The pyrimidine compound according to any one of [1] to [6], wherein R3 is hydrogen;
[9] The pyrimidine compound according to any one of [1] to [8], wherein Q is oxygen; [10] The pyrimidine compound according to any one of [1] to [9], wherein R5 is a Cl-ClO alkyl or C3-C10 alkenyl group substituted with halogen or -L3R14;
[11] The pyrimidine compound according to any one of [1] to [10], wherein R5 is a Cl-ClO alkyl or C3-C10 alkenyl group substituted with halogen;
[12] The pyrimidine compound according to [1], wherein
Q is oxygen,
G1 is nitrogen or CR6 ,
R1 and R6 are the same or different and represent hydrogen, halogen or a chain C1-C6 hydrocarbon group optionally substituted with halogen,
R2 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L1R7, R3 is hydrogen or a chain C1-C6 hydrocarbon group optionally substituted with halogen,
R4 is hydrogen, halogen or a chain C1-C6 hydrocarbon group optionally substituted with halogen, and
R5 is a Cl-ClO alkyl or C3-C10 alkenyl group substituted with halogen or -L3R14;
[13] A pest controlling agent comprising the pyrimidine compound according to any one of [1] to [12] and an inert carrier;
[14] Use of the pyrimidine compound according to any one of [1] to [12] for controlling pests; and
[15] A method of controlling pests, which comprises a step of applying an effective amount of the pyrimidine compound according to any one of [1] to [12] to pests or habitats of the pests. [16] 4- (2,2,3,3-tetrafluoropropoxy) -6- ( [1,2, 4] triazol-1-yl) - pyrimidine.
[17] 5-methyl-4- (2,2,3, 3-tetrafluoropropoxy) -6-
( [1, 2,4] triazol-1-yl) -pyrimidine.
[18] 5-chloro-4- (2,2,3, 3-tetrafluoropropoxy) -6- ([1,2,4] triazol-1-yl) -pyrimidine.
[19] 4- (2, 2, 3, 4, 4, 4-hexafluorobutyloxy) -6- ( [1, 2, 4 ] triazol-1- yl ) -pyrimidine .
[20] . 4- (2, 2, 3, 4, 4, 4-hexafluorobutyloxy) -5-methyl-6-
( [1, 2, 4] triazol-1-yl) -pyrimidine. [21] 5-chloro-4- (2,2,3,4,4, 4-hexafluorobutyloxy) -S-
( [l,2,4]triazol-l-yl) -pyrimidine.
[22] 4- (2,2,3, 3,4, 4 , 5, 5-octafluoropentyloxy) -5-methyl-6- ( [l,2,4]triazol-l-yl) -pyrimidine. [23] 5-chloro-4- (2,2, 3, 3, 4, 4, 5, 5-octafluoropentyloxy) -6- ( [l,2,4]triazol-l-yl) -pyrimidine.
[24] 4- (2-chloro-2-methylpropoxy) -5-methyl-6-
( [l,2,4]triazol-l-yl) -pyrimidine.
[25] 4- (2, 2-dichloropropoxy) -5-methyl-6- ([1,2, 4] triazol-1- yl) -pyrimidine.
[26] A compound represented by formula (4) :
Figure imgf000008_0001
wherein
Q represents oxygen, R3 represents hydrogen,
R4 represents hydrogen, halogen, or a chain C1-C6 hydrocarbon group,
R5 represents a Cl-ClO alkyl group substituted with one or more halogen, or a C3-C10 alkenyl group substituted with one or more halogen.
[27 ] A compound represented by formula (2) :
Figure imgf000008_0002
wherein G1 represents nitrogen or CR6 ,
R6 represents hydrogen,
R1 represents hydrogen, or halogen,
R2 represents hydrogen, halogen, or an amino group,
R3 represents hydrogen,
R4 represents halogen, a nitro group, a cyano group, or a chain C1-C6 hydrocarbon group optionally substituted with halogen.
[28] A compound represented by formula (6) :
Figure imgf000009_0001
wherein
G1 represents nitrogen or CR6 ,
R6 represents hydrogen,
R1 represents hydrogen, or halogen, R2 represents hydrogen, halogen, or an amino group,
R3 represents hydrogen,
R4 represents halogen, a nitro group, a cyano group, or a chain C1-C6 hydrocarbon group optionally substituted with halogen.
Mode for Carrying Out the Invention
In the present compound, the "halogen" includes fluorine, chlorine, bromine and iodine.
In the present compound, the "chain C1-C6 hydrocarbon group" includes, for example, C1-C6 alkyl groups such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isopentyl group, 1- methylbutyl group, a tert-pentyl group, a neopentyl group, a hexyl group and an isohexyl group; C2-C6 alkenyl groups such as a vinyl group, a 2-propenyl group, a 2-butenyl group, a 3-butenyl group, a 2-methyl-2- propenyl group, a 3-methyl-2-butenyl group, a 2-pentenyl group and a 2-hexenyl group; and C2-C6 alkynyl groups such as an ethynyl group, a 2-propynyl group, a 2-butynyl group and a 3-butynyl group.
In the present compound, the "chain C1-C6 hydrocarbon group optionally substituted with halogen" includes, for example, C1-C6 alkyl groups optionally substituted with halogen, such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isopentyl group, a 1-methylbutyl group, a tert-pentyl group, a neopentyl group, a hexyl group, an isohexyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a 2, 2, 2-trifluoroethyl group, a 2, 2, 2-trichloroethyl group, a pentafluoroethyl group, a perfluoropropyl group, a perfluorobutyl group and a perfluorohexyl group; C2-C6 alkenyl group optionally substituted with halogen, such as a vinyl group, a 2-propenyl group, a 3-chloro-2- propenyl group, a 2-chloro-2-propenyl group, a 3, 3-dichloro- 2-propenyl group, a 2-butenyl group, a 3-butenyl group, a 2- methyl-2-propenyl group, a 3-methyl-2-butenyl group, a 2- pentenyl group and a 2-hexenyl group; and C2-C6 alkynyl group optionally substituted with halogen, such as an ethynyl group, a 2-propynyl group, a 2-butynyl group, a 3-butynyl group, a 3-chloro-2-propynyl group and a 3-bromo-2-propynyl group. In the present compound, the "phenyl group optionally substituted with one or more members selected from Group A" includes, for example, a phenyl group, a 2-chlorophenyl group, a 3-chlorophenyl group, a 4-chlorophenyl group, a 2- aminophenyl group, a 3-aminophenyl group, a 4-aminophenyl group, a 2-cyanophenyl group, a 3-cyanophenyl group, a 4- cyanophenyl group, a 2-nitrophenyl group, a 3-nitrophenyl group, a 4-nitrophenyl group, a 2-methylphenyl group, a 3- methylphenyl group, a 4-methylphenyl group, a 2- (trifluoromethyl) phenyl group, a 3- (trifluoromethyl) phenyl group, a 4- (trifluoromethyl) phenyl group, a 2-methoxyphenyl group, a 3-methoxyphenyl group, a 4-methoxyphenyl group, a 4- (trifluoromethoxy) phenyl group, a 4- (methylthio) phenyl group, a 4- (methylsulfinyl) phenyl group and a 4- (methylsulfonyl) phenyl group. In the present compound, the "5- or 6-membered aromatic heterocyclic group" includes, for example, a 2- pyrrolyl group, a 2-furyl group, a 3-furyl group, a 2- thienyl group, a 3-thienyl group, a 5-pyrazolyl group, a 4- pyrazolyl group, a 2-pyridinyl group, a 3-pyridinyl group, a 4-pyridinyl group, a pyrazinyl group, 1-pyrrolyl group and 1-pyrazolyl group.
In the present compound, the "5- or 6-membered aromatic heterocyclic group optionally substituted with one or more members selected from Group A" includes, for example, a l-methyl-2-pyrrolyl group, a 2-furyl group, a 3-furyl group, a 5-bromo-2-furyl group, a 5-nitro-2-furyl group, a 2-methyl-3-furyl group, a 2, 5-dimethyl-3-furyl group, a 2,4- dimethyl-3-furyl group, a 2-thienyl group, a 3-thienyl group, a 5-methyl-2-thienyl group, a 3-methyl-2-thienyl group, a 1- methyl-3-trifluoromethyl-5-pyrazolyl group, a 5-chloro-l, 3- dimethyl-4-pyrazolyl group, a 2-pyridinyl group, a 3- pyridinyl group, a 4-pyridinyl group, a 2-methyl-3-pyridinyl group, a 6-methyl-3-pyridinyl group, a 2-chloro-3-pyridinyl group, a 6-chloro-3-pyridinyl group, a pyrazinyl group, a 1- pyrrolyl group and a 1-pyrazolyl group.
In the present compound, the "C1-C6 alkoxy group optionally substituted with halogen" includes, for example, a methoxy group, a trifluoromethoxy group, an ethoxy group, a 2, 2, 2-trifluoroethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, an isobutyloxy group, a sec-butyloxy group, a tert-butyloxy group, a pentyloxy group and a hexyloxy group.
In the present compound, the "C1-C6 alkylsulfonyl group optionally substituted with halogen" includes, for example, a methylsulfonyl group, a trifluoromethylsulfonyl group and an ethylsulfonyl group.
In the present compound, the "C1-C4 alkylamino group optionally substituted with halogen" includes, for example, a methylamino group, an ethylamino group, a 2,2,2- trifluoroethylamino group, a propylamino group, an isopropylamino group and a butylamino group.
In the present compound, the "C2-C8 dialkylamino group optionally substituted with halogen" includes, for example, a dimethylamino group, a diethylamino group, a bis (2,2, 2- trifluoroethyl) amino group and a dipropylamino group.
In the present compound, the "C3-C8 cycloalkyl group optionally substituted with halogen" includes, for example, a cyclopropyl group, a 2, 2-difluorocyclopropyl group, a 2,2- dichlorocyclopropyl group, a 2, 2-dibromocyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group and a cyclooctyl group.
In the present compound, the "Cl-ClO alkyl group substituted with one or more members selected from Group B" includes, for example, a 2, 2-dichloropropyl group, a 2- chloro-2-methylpropyl group, a 2, 2, 2-trichloroethyl group, a l-methyl-2, 2, 2-trichloroethyl group, a monofluoromethyl group, a difluoromethyl group, a trifluoromethyl group, 1,1- difluoroethyl group, a 2, 2-difluoroethyl group, 1,2,2- trifluoroethyl group, a 2, 2, 2-trifluoroethyl group, a 1, 1, 2, 2-tetrafluoroethyl group, a 1, 1, 2, 2, 2-pentafluoroethyl group, 1-fluoropropyl group, a 2-fluoropropyl group, a 3- fluoropropyl group, 1, 1-difluoropropyl group, a 2,2- difluoropropyl group, a 3, 3-difluoropropyl group, a 2,3,3- trifluoropropyl group, a 3, 3, 3-trifluoropropyl group, a 2, 2, 3, 3-tetrafluoropropyl group, a 2,2,3,3,3- pentafluoropropyl group, a 1, 1, 2, 3, 3, 3-hexafluoropropyl group, a 1, 1, 2, 2, 3, 3, 3-heptafluoropropyl group, a 1,1- bis (trifluoromethyl) methyl group, a perfluoroisopropyl group, a 2, 3, 3, 3-tetrafluoro-2- (trifluoromethyl) propyl group, a 4- fluorobutyl group, a 2-fluorobutyl group, a 2,2- difluorobutyl group, a 3-fluorobutyl group, a 3,3- difluorobutyl group, a 4, 4-difluorobutyl group, a 4,4,4- trifluorobutyl group, a 2, 2, 3-trifluorobutyl group, a 2, 2, 3, 3-tetrafluorobutyl group, a 2, 2, 3, 4-tetrafluorobutyl group, a 3, 3, 4, 4-tetrafluorobutyl group, a 2,2,3,4,4- pentafluorobutyl group, a 2, 2, 3, 4, 4, 4-hexafluorobutyl group, a 2,2, 3,3, 4 , 4-hexafluorobutyl group, a 2,2,3,3,4,4,4- heptafluorobutyl group, a 1, 1, 2, 2, 3, 3, 4, 4-octafluorobutyl group, a 2-methoxyethyl group, a 2-trifluoromethoxyethyl group, a 2-tert-butyloxyethyl group, a 2-(tert- butylthio) ethyl group, a 2-dimethylaminoethyl group, a 2- (dimethylamino) -2-methyl-propyl group, 1-
(trimethylsilyl) methyl group, a 2- (trimethylsilyl) ethyl group, a 2- (methylamino) ethyl group, a 2- (ethylamino) ethyl group, a 2- (2, 2, 2-trifluoroethylaπiino) ethyl group, a 2- (propylamino) ethyl group, a 2- (isopropylamino) ethyl group, a 2- (butylamino) ethyl group, a 2- (methoxycarbonyl) ethyl group and a 2- (tert-butyloxycarbonyl) ethyl group.
In the present compound, the "C3-C10 alkenyl group substituted with one or more members selected from Group B" includes, for example, a 3, 3-dichloro-2-propenyl group, a 2, 3, 3-trichloro-2-propenyl group, a 3, 3-difluoro-2-propenyl group, a 2, 3-difluoro-2-propenyl group, a 4, 4, 4-trifluoro-2- butenyl group, a 2, 3, 4, 4, 4-pentafluoro-2-butenyl group, a 4- methoxy-2-propenyl group, a 4-methylthio-2-propenyl group and a 4-dimethylamino-2-propenyl group. In the present compound, the "C1-C6 alkyl group optionally substituted with halogen" includes, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isopentyl group, a 1- methylbutyl group, a tert-pentyl group, a neopentyl group, a hexyl group, an isohexyl group, a 1, 1, 1-trifluoromethyl group, a 2, 2, 2-trifluoroethyl group and a 2,2,2- trichloroethyl group.
Examples of the present compound includes the following pyrimidine compounds.
A pyrimidine compound represented by formula (1), wherein Q is oxygen. a pyrimidine compound represented by formula (1), wherein, Q is -S(O)n-.
A pyrimidine compound represented by formula (1), wherein, n is 0.
A pyrimidine compound represented by formula (1), wherein, n is 1.
A pyrimidine compound represented by formula (1), wherein n is 2.
A pyrimidine compound represented by formula (1), wherein R1 is hydrogen, halogen, a nitro group, a cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen,
-L1R7 or a -C(=O)R8.
A pyrimidine compound represented by formula (1), wherein R1 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, -L1R7 or a -C(=O)R8. A pyrimidine compound represented by formula (1), wherein R1 is hydrogen, halogen or a chain C1-C6 hydrocarbon group optionally substituted with halogen.
A pyrimidine compound represented by formula (1), wherein R1 is hydrogen. A pyrimidine compound represented by formula (1), wherein R2 is hydrogen, halogen, a nitro group, a cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, -L1R7 or -C(=0)R8. A pyrimidine compound represented by formula (1), wherein R2 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen or -L1R7. A pyrimidine compound represented by formula (1), wherein R2 is hydrogen, halogen or a chain C1-C6 hydrocarbon group optionally substituted with halogen.
A pyrimidine compound represented by formula (1), wherein R2 is hydrogen.
A pyrimidine compound represented by formula (1), wherein R1 and R2 are the same or different and represent hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L1R7.
A pyrimidine compound represented by formula (1), wherein R1 and R2 are hydrogen.
A pyrimidine compound represented by formula (1), wherein G1 is nitrogen.
A pyrimidine compound represented by formula (1), wherein G1 is CR6. A pyrimidine compound represented by formula (1), wherein G1 is CR6 and R6 is hydrogen.
A pyrimidine compound represented by formula (1), wherein R1 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, -L1R7 or -C(=O)R8, R2 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen or -L1R7, G1 is nitrogen or CR6, and R6 is hydrogen.
A pyrimidine compound represented by formula (1), wherein R1 is hydrogen, halogen or a chain C1-C6 hydrocarbon group optionally substituted with halogen, R2 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L1R7, G1 is nitrogen or CR6, and R6 is hydrogen. A pyrimidine compound represented by formula (1), wherein R1 is hydrogen, R2 is hydrogen or an amino group, G1 is nitrogen or CR6, and R6 is hydrogen.
A pyrimidine compound represented by formula (1), wherein R3 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or a C3-C8 cycloalkyl group optionally substituted with halogen.
A pyrimidine compound represented by formula (1), wherein R3 is hydrogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L2R10.
A pyrimidine compound represented by formula (1), wherein R3 is hydrogen or a chain C1-C6 hydrocarbon group optionally substituted with halogen.
A pyrimidine compound represented by formula (1), wherein R3 is hydrogen.
A pyrimidine compound represented by formula (1), wherein R4 is hydrogen, halogen, a nitro group, a cyano group, a chain
C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen,
-L2R10 or -Ct=O)R11.
A pyrimidine compound represented by formula (1), wherein R4 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, -L2R10, or a phenyl group optionally substituted with one or more members selected from Group A. A pyrimidine compound represented by formula (1), wherein R4 is hydrogen, halogen, a nitro group, a cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, or -C(=O)R11. A pyrimidine compound represented by formula (1), wherein R4 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, or -L2R10. A pyrimidine compound represented by formula (1), wherein R4 is hydrogen, chlorine or a methyl group.
A pyrimidine compound represented by formula (1), wherein R3 is hydrogen, R4 is hydrogen, halogen, a nitro group, a cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, -L2R10 or -CC=O)R11.
A pyrimidine compound represented by formula (1), wherein R3 is hydrogen, and R4 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or - L2R10. A pyrimidine compound represented by formula (1), wherein R3 is hydrogen, and R4 is hydrogen, chlorine or a methyl group.
A pyrimidine compound represented by formula (1), wherein R1, R2 and R6 are the same or different and represent hydrogen, halogen, a nitro group, a cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, -L1R7 or -C(=O)R8.
A pyrimidine compound represented by formula (1), wherein R1, R2 and R6 are the same or different and represent hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, -L1R7 or -C(=O)R8.
A pyrimidine compound represented by formula (1), wherein R1 and R6 are the same or different and represent hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -C(=O)R8.
A pyrimidine compound represented by formula (1), wherein R1 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, -L1R7, or -C(=O)R8, R2 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L1R7, G1 is nitrogen or CR6, R6 is hydrogen, R3 is hydrogen, and R4 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen or -L2R10.
A pyrimidine compound represented by formula (1), wherein R1 is hydrogen, halogen, or a chain C1-C6 hydrocarbon group optionally substituted with halogen, R2 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L1R7, G1 is nitrogen or CR6, R6 is hydrogen, R3 is hydrogen, and R4 is hydrogen, halogen, A chain C1-C6 hydrocarbon group optionally substituted with halogen, or - L2R10. A pyrimidine compound represented by formula (1), wherein R5 is a Cl-ClO alkyl group substituted with halogen or -L3R14, and L3 is oxygen, sulfur or -Si(R17)2-.
A pyrimidine compound represented by formula (1), wherein R5 is a Cl-ClO alkyl group substituted with -L3R14.
A pyrimidine compound represented by formula (1), wherein R5 is a Cl-ClO alkyl group substituted with -L3R14, and L3 is oxygen, sulfur or -Si(R17 ) 2 -■
A pyrimidine compound represented by formula (1), wherein R5 is a Cl-ClO alkyl group substituted with halogen.
A pyrimidine compound represented by formula (1), wherein R5 is a Cl-ClO alkyl group substituted with one to eight halogen.
A pyrimidine compound represented by formula (1), wherein R5 is a C2-C6 alkyl group substituted with one to eight halogen.
A pyrimidine compound represented by formula (1), wherein R5 is a C3-C6 alkyl group substituted with one to eight halogen.
A pyrimidine compound represented by formula (1), wherein R5 is a Cl-ClO alkyl group substituted with one to eight fluorine.
A pyrimidine compound represented by formula (1), wherein R5 is a C2-C6 alkyl group substituted with one to eight fluorine.
A pyrimidine compound represented by formula (1), wherein R5 is a C3-C6 alkyl group substituted with one to eight fluorine .
A pyrimidine compound represented by formula (1), wherein R5 is a Cl-ClO alkyl group substituted with one to eight chlorine. A pyrimidine compound represented by formula (1), wherein R5 is a 2, 2-dichloropropyl group, a 2-chloro-2-methylpropyl group, a 2, 2, 2-trichloroethyl group, a l-methyl-2, 2, 2- trichloroethyl group, a 2, 2, 3, 3-tetrafluoropropyl group, a 2, 2, 3, 3, 3-pentafluoropropyl group, a 1,1- bis (trifluoromethyl) methyl group, a perfluoroisopropyl group, a 4, 4, 4-trifluorobutyl group, a 2,2,3,3,4,4,4- heptafluorobutyl group, a 2, 2, 3, 4, 4, 4-hexafluorobutyl group, a 2, 2, 3, 3, 4, 4-hexafluorobutyl group, a 2,2- bis (trifluoromethyl) propyl group, a 2-methyl-2-
(trifluoromethyl) propyl group or a 2,2,3,3,4,4,5,5- octafluoropentyl group.
A pyrimidine compound represented by formula (1), wherein R5 is a C3-C10 alkenyl group substituted with halogen or -L3R14, and L3 is oxygen, sulfur or -Si(R17J2--
A pyrimidine compound represented by formula (1), wherein R5 is a C3-C10 alkenyl group substituted with -L3R14, and L3 is oxygen, sulfur or -Si(R17J2-. A pyrimidine compound represented by formula (1), wherein R5 is a C3-C10 alkenyl group substituted with halogen.
A pyrimidine compound represented by formula (1), wherein R5 is a C3-C10 alkenyl group substituted with one to eight halogen. A pyrimidine compound represented by formula (1), wherein R5 is C3-C6 alkenyl group substituted with one to eight halogen.
A pyrimidine compound represented by formula (1), wherein R5 is C3-C10 alkenyl group substituted with one to eight fluorine . A pyrimidine compound represented by formula (1), wherein R5 is a C3-C6 alkenyl group substituted with one to eight fluorine.
A pyrimidine compound represented by formula (1), wherein R5 is a C3-C10 alkenyl group substituted with one to eight chlorine .
A pyrimidine compound represented by formula (1) , wherein R5 is a 3, 3-dichloro-2-propenyl group, a 2, 3, 3-trichloro-2- propenyl group, a 3, 3-difluoro-2-propenyl group, a 4,4,4- trifluoro-2-butenyl group or a 2, 3, 4, 4, 4-pentafluoro-2- butenyl group.
A pyrimidine compound represented by formula (1), wherein R5 is a Cl-ClO alkyl or C3-C10 alkenyl group substituted with halogen or -L3R14.
A pyrimidine compound represented by formula (1), wherein R5 is a Cl-ClO alkyl or C3-C10 alkenyl group substituted with halogen or -L3R14, L3 is oxygen, sulfur or -Si(R17) 2 -. A pyrimidine compound represented by formula (1), wherein R5 is a Cl-ClO alkyl or C3-C10 alkenyl group substituted with - L3R14, L3 is oxygen, sulfur, or -Si(R17J2-.
A pyrimidine compound represented by formula (1), wherein R5 is a Cl-ClO alkyl or C3-C10 alkenyl group substituted with halogen. A pyrimidine compound represented by formula (1), wherein Q is oxygen, R5 is a Cl-ClO alkyl or C3-C10 alkenyl group substituted with halogen or -L3R14, and L3 is oxygen, sulfur or -Si(R17 )2-. A pyrimidine compound represented by formula (1), wherein Q is oxygen, R5 is a Cl-ClO alkyl or C3-C10 alkenyl group substituted with -L3R14, and L3 is oxygen, sulfur or -
Si(R17J2--
A pyrimidine compound represented by formula (1), wherein Q is oxygen, and R5 is a Cl-ClO alkyl or C3-C10 alkenyl group substituted with halogen.
A pyrimidine compound represented by formula (1), wherein
Q is oxygen,
R5 is a 2, 2-dichloropropyl group, a 2-chloro-2-methylpropyl group, a 2, 2, 2-trichloroethyl group, a l-methyl-2, 2, 2- trichloroethyl group, a 2, 2, 3, 3-tetrafluoropropyl group, a
2, 2, 3, 3, 3-pentafluoropropyl group, a 1,1- bis (trifluoromethyl) methyl group, a perfluoroisopropyl group, a 4, 4, 4-trifluorobutyl group, a 2,2,3,3,4,4,4- heptafluorobutyl group, a 2, 2, 3, 4, 4, 4-hexafluorobutyl group, a 2, 2, 3, 3, 4, 4-hexafluorobutyl group, a 2,2- bis (trifluoromethyl) propyl group, a 2-methyl-2-
(trifluoromethyl) propyl group, a 2,2,3,3,4,4,5,5- octafluoropentyl group, a 3, 3-dichloro-2-propenyl group, a 2, 3, 3-trichloro-2-propenyl group, a 3, 3-difluoro-2-propenyl group, a 4, 4 , 4-trifluoro-2-butenyl group or a 2,3,4,4,4- pentafluoro-2-butenyl group.
A pyrimidine compound represented by formula (1), wherein, Q is oxygen,
G1 is nitrogen, or CR6 ,
R1 and R6 are the same or different and represent hydrogen, halogen, or a chain C1-C6 hydrocarbon group optionally substituted with halogen, R2 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L1R7, R3 is hydrogen or a chain C1-C6 hydrocarbon group optionally substituted with halogen, R4 is hydrogen, halogen, or a chain C1-C6 hydrocarbon group optionally substituted with halogen, and
R5 is a Cl-ClO alkyl or C3-C10 alkenyl group substituted with halogen or -L3R14.
A pyrimidine compound represented by formula (1), wherein
Q is oxygen,
G1 is nitrogen or CR6 ,
R1 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, -L1R7, or -C(=O)R8, R2 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L1R7,
R6 is hydrogen,
R3 is hydrogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L2R10, R4 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, or -L2R10, and
R5 is a Cl-ClO alkyl group substituted with one or more members selected from Group B, a C3-C10 alkenyl group substituted with or one or more members selected from Group
B.
A pyrimidine compound represented by formula (1), wherein Q is oxygen, G1 is nitrogen, or CR6 ,
R1 is hydrogen, halogen, or a chain C1-C6 hydrocarbon group optionally substituted with halogen,
R2 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L1R7, R6 is hydrogen,
R3 is hydrogen or a chain C1-C6 hydrocarbon group optionally substituted with halogen,
R4 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L2R10,
R5 is a Cl-ClO alkyl or C3-C10 alkenyl group substituted with halogen or -L3R14, and
L3 is oxygen, sulfur or -Si(R17) 2 -•
A pyrimidine compound represented by formula (1), wherein Q is oxygen,
G1 is a nitrogen or CR6 ,
R1 is hydrogen, a halogen or a methyl group, R2 is hydrogen, halogen, a methyl group or an amino group, R6 is hydrogen,
R3 is hydrogen, aa cchhaaiinn CCll--CCββ hhydrocarbon group optionally substituted with halogen, or -L2R10, RR44 iiss hhyyddrrooggeenn,, hhaallooggeenn,, aa cchhaaiinn CCl1--C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, or -L2R10,
R5 is a Cl-ClO alkyl or C3-C10 alkenyl group substituted with halogen or -L3R14, and
L3 is oxygen, sulfur or -Si(R17) 2 -. A pyrimidine compound represented by formula (1), wherein, Q is oxygen,
G1 is nitrogen or CR6 , R1 is hydrogen or halogen, R2 is hydrogen, halogen, a methyl group or an amino group, R6 is hydrogen,
R3 is hydrogen or a chain C1-C6 hydrocarbon group optionally substituted with halogen,
R4 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L2R10,
R5 is a Cl-ClO alkyl or C3-C10 alkenyl group substituted with halogen or -L3R14, and
L3 is oxygen, sulfur or -Si(R17 )2--
A pyrimidine compound represented by formula (1), wherein Q is oxygen, G1 is nitrogen or CR6 , R1 is hydrogen, R2 is hydrogen or an amino group, R6 is hydrogen, R3 is hydrogen, R4 is hydrogen, halogen, or a chain C1-C6 hydrocarbon group optionally substituted with halogen, and R5 is an Cl-ClO alkyl or C3-C10 alkenyl group substituted with halogen or - L3R14, L3 is oxygen, sulfur or -Si(R17 )2-.
A pyrimidine compound represented by formula (1), wherein Q is oxygen, G1 is nitrogen or CR6 , R1 is hydrogen or halogen, R2 is hydrogen, halogen, a methyl group, or an amino group, R6 is hydrogen, R3 is hydrogen or a chain C1-C6 hydrocarbon group optionally substituted with halogen, R4 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L2R10, and R5 is a Cl-ClO alkyl or C3-C10 alkenyl group substituted with halogen. A pyrimidine compound represented by formula (1), wherein Q is oxygen, G1 is nitrogen, R1 is hydrogen or halogen, R2 is hydrogen, halogen, or an amino group, R3 is hydrogen, R4 is hydrogen, halogen, a chain Cl-Cβ hydrocarbon group optionally substituted with halogen, and R5 is a Cl-ClO alkyl or C3-C10 alkenyl group substituted with halogen.
Production Processes of the present compound will be described below.
The present compound can be produced, for example, in accordance with the following (Production Process A) to (Production Process E).
(Production Process A)
Among the present compound, the compound represented by formula (1-i) :
Figure imgf000027_0001
wherein R1 , R2 , R3 , R4 , R5 and G1 are as defined above, and Q' represents oxygen or sulfur (hereinafter referred to as the present compound (1-i)) can be produced by reacting the compound represented by formula (2) :
Figure imgf000027_0002
wherein R1 , R2 , R3 , R4 and G1 are as defined above (hereinafter referred to as the compound (2) ) with the compound represented by formula (3) :
R5-Q'-H wherein R5 and Q' are as defined above (hereinafter referred to as the compound (3) ) .
The reaction is performed in the presence or absence of a solvent. The solvent used in the reaction includes, for example, water; ethers such as 1,4-dioxane, diethylether, tetrahydrofuran and tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane and chlorobenzene; hydrocarbons such as toluene, benzene and xylene; nitriles such as acetonitrile; aprotic polar solvents such as N, N- dimethylformamide, N-methyl pyrrolidone (hereinafter referred to as NMP), 1, 3-dimethyl-2-imidazolidinone and dimethyl sulfoxide; and mixtures thereof.
The amount of the compound (3) used in the reaction is usually from 1 to 2 mol per 1 mol of the compound (2) .
The reaction is usually performed in the presence of a base. The base used in the reaction includes, for example, nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2, 6-lutidine, 1, 8-diazabicyclo [5, 4, 0] 7-undecene (hereinafter referred to as DBU) and 1,5- diazabicyclo [4 , 3, 0] 5-nonene; tertiary amines such as triethylamine and N, N-diisopropylethylamine; and inorganic bases such as potassium carbonate and sodium hydride. The amount of the base used in the reaction is usually
1 mol or more per 1 mol of the compound (2) .
The reaction temperature of the reaction is usually within a range from -20 to 100°C. The reaction time of the reaction is usually within a range from 0.1 to 24 hours.
After completion of the reaction, the present compound
(1-i) can be isolated by pouring the reaction mixture into water followed by extraction with an organic solvent and subsequent concentration of the organic layer; pouring the reaction mixture into water followed by collection of the formed solid by filtration; or collecting a solid formed in the reaction mixture by filtration. The isolated present compound (1-i) can also be further purified by recrystallization, chromatography and so on.
The compound (2) includes, for example, the following pyrimidine compounds .
A pyrimidine compound represented by formula (2), wherein G1 is nitrogen. A pyrimidine compound represented by formula (2), wherein G1 is CR6 and R6 is hydrogen.
A pyrimidine compound represented by formula (2), wherein R1 is hydrogen;
A pyrimidine compound represented by formula (2), wherein R2 is hydrogen.
A pyrimidine compound represented by formula (2), wherein R1 and R2 are hydrogen.
A pyrimidine compound represented by formula (2), wherein G1 is nitrogen, R1 and R2 is hydrogen. A pyrimidine compound represented by formula (2), wherein R3 is hydrogen.
A pyrimidine compound represented by formula (2), wherein G1 is nitrogen and R3 is hydrogen. A pyrimidine compound represented by formula (2), wherein G1 is CR6, R6 is hydrogen and R3 is hydrogen.
A pyrimidine compound represented by formula (2), wherein R4 is hydrogen, halogen, a nitro group, a cyano. group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen or -CC=O)R11.
A pyrimidine compound represented by formula (2), wherein R4 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen or -L2R10.
A pyrimidine compound represented by formula (2), wherein R4 is halogen, a nitro group, a cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3- C8 cycloalkyl group optionally substituted with halogen or - CC=O)R11.
A pyrimidine compound represented by formula (2), wherein R3 is hydrogen and R4 is hydrogen, halogen, a nitro group, A cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, -L2R10 or -CC=O)R11.
A pyrimidine compound represented by formula (2), wherein R3 is hydrogen and R4 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen or - L2R10. A pyrimidine compound represented by formula (2), wherein R3 is hydrogen and R4 is halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen or -L2R10. A pyrimidine compound represented by formula (2), wherein R3 is hydrogen and R4 is hydrogen, chlorine or a methyl group. A pyrimidine compound represented by formula (2), wherein G1 is nitrogen or CR6' R6 is hydrogen, R1 is hydrogen or halogen, R2 is hydrogen, halogen, or an amino group, R3 is hydrogen, R4 is halogen, a nitro group, a cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen.
A pyrimidine compound represented by formula (2), wherein G1 is nitrogen, R1 is hydrogen or halogen, R2 is hydrogen, halogen, or an amino group, R3 is hydrogen, R4 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen.
A pyrimidine compound represented by formula (2), wherein G1 is nitrogen, R1 and R2 are hydrogen, R3 is hydrogen, R4 is hydrogen, chlorine, or a methyl group.
(Production Process B)
The present compound (1-i) can be produced by reacting the compound represented by formula (4):
R3
(4)
'Q1'
R4 wherein R , R r^ 4 , „R5 and Q' are as defined above (hereinafter referred to as the compound (4)) with the compound represented by formula (5) :
Figure imgf000032_0001
wherein R1 , R2 and G1 are as defined above (hereinafter referred to as the compound (5)) .
The reaction is performed in the presence or absence of a solvent. The solvent used in the reaction includes, for example, water; ethers such as 1,4-dioxane, diethylether, tetrahydrofuran and tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane and chlorobenzene; hydrocarbons such as toluene, benzene and xylene; nitriles such as acetonitrile; aprotic polar solvents such as N, N- dimethylformamide, NMP, 1, 3-dimethyl-2-imidazolidinone and dimethyl sulfoxide; and mixtures thereof. The amount of the compound (5) used in the reaction is usually from 1 to 2 mol per 1 mol of the compound (4) .
The reaction is usually performed in the presence of a base .
The base used in the reaction includes, for example, nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2, 6-lutidine, DBU and 1, 5-diazabicyclo [4 , 3, 0] 5- nonene; tertiary amines such as triethylamine and N, N- diisopropylethylamine; and inorganic bases such as potassium carbonate and sodium hydride. The amount of the base used in the reaction is usually 1 mol or more per 1 mol of the compound (4) .
The reaction temperature of the reaction is usually within a range from -20 to 1000C. The reaction time of the reaction is usually within a range from 0.1 to 24 hours.
After completion of the reaction, the present compound
(1-i) can be isolated by pouring the reaction mixture into water followed by extraction with an organic solvent and subsequent concentration of the organic layer; pouring the reaction mixture into water followed by collection of the formed solid by filtration; or collecting a solid formed in the reaction mixture by filtration. The isolated present compound (1-i) can also be further purified by recrystallization, chromatography and so on.
The compound (4) includes, for example, the following pyrimidine compounds . A pyrimidine compound represented by formula (4), wherein R3 is hydrogen.
A pyrimidine compound represented by formula (4), wherein R4 is hydrogen, halogen, a nitro group, a cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, or -CC=O)R11.
A pyrimidine compound represented by formula (4), wherein R4 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, or -L2R10.
A pyrimidine compound represented by formula (4), wherein R3 is hydrogen, R4 is hydrogen, halogen, a nitro group, a cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, -L2R10 or -CC=O)R11. A pyrimidine compound represented by formula (4), wherein R3 is hydrogen, R4 is hydrogen, halogen, or a chain C1-C6 hydrocarbon group optionally substituted with halogen. A pyrimidine compound represented by formula (4), wherein R3 is hydrogen, R4 is hydrogen, chlorine or a methyl group. A pyrimidine compound represented by formula (4), wherein R5 is a Cl-ClO alkyl or C3-C10 alkenyl group substituted with halogen or -L3R14. A pyrimidine compound represented by formula (4), wherein R5 is a Cl-ClO alkyl or C3-C10 alkenyl group substituted with halogen or -L3R14, and L3 is oxygen, sulfur or -Si(R17J2-- A pyrimidine compound represented by formula (4), wherein R5 is a Cl-ClO alkyl or C3-C10 alkenyl group substituted with - L3R14, and L3 is oxygen, sulfur or -Si(R17J2-.
A pyrimidine compound represented by formula (4), wherein R5 is a Cl-ClO alkyl or C3-C10 alkenyl group substituted with halogen.
A pyrimidine compound represented by formula (4), wherein Q is oxygen, R5 is a Cl-ClO alkyl or C3-C10 alkenyl group substituted with halogen or -L3R14, and L3 is oxygen, sulfur or -Si(R17 )2-.
A pyrimidine compound represented by formula (4), wherein Q is oxygen, R5 is a Cl-ClO alkyl or C3-C10 alkenyl group substituted with -L3R14, and L3 is oxygen, sulfur or - Si(R17)2-.
A pyrimidine compound represented by formula (4), wherein Q is oxygen, and R5 is a Cl-ClO alkyl or C3-C10 alkenyl group substituted with halogen. A pyrimidine compound represented by formula (4), wherein R4 is hydrogen, halogen, or a chain C1-C6 hydrocarbon group optionally substituted with halogen.
A pyrimidine compound represented by formula (4), wherein R5 is Cl-ClO alkyl group substituted with fluorine, or C3-C10 alkenyl group substituted with fluorine.
A pyrimidine compound represented by formula (4), wherein Q is oxygen, R3 is hydrogen, R4 is hydrogen, halogen, or a chain C1-C6 hydrocarbon group, and R5 is Cl-ClO alkyl group substituted with halogen, or C3-C10 alkenyl group substituted with halogen.
A pyrimidine compound represented by formula (4), wherein Q is oxygen, R3 is hydrogen, R4 is hydrogen, chlorine, or a methyl group, and R5 is Cl-ClO alkyl group substituted with fluorine, or C3-C10 alkenyl group substituted with fluorine. A pyrimidine compound represented by formula (4), wherein Q is oxygen, R3 is hydrogen, R4 is hydrogen, chlorine, or a methyl group, and R5 is 2, 2-dichloropropyl group, 2-chloro- 2-methylpropyl group, 2, 2, 2-trichloroethyl group, 1-methyl- 2, 2, 2-trichloroethyl group, 2, 2, 3, 3-tetrafluoropropyl group, 2, 2, 3, 3, 3-pentafluoropropyl group, 1,1- bis (trifluoromethyl) methyl group, perfluoroisopropyl group, 4, 4, 4-trifluorobutyl group, 2, 2, 3, 3, 4, 4, 4-heptafluorobutyl group, 2, 2, 3, 4, 4, 4-hexafluorobutyl group, 2,2,3,3,4,4- hexafluorobutyl group, 2, 2-bis (trifluoromethyl) propyl group, 2-methy-2- (trifluoromethyl) propyl group, . or 2,2,3,3,4,4,5,5- octafluoropentyl group.
(Production Process C) The present compound (1-i) can be produced by reacting the compound represented by formula (6) :
Figure imgf000036_0001
wherein R1 , R2 , R3 , R4 and G1 are as defined above] (hereinafter referred to as the compound (6)) with the compound (3) .
The reaction is performed in the presence or absence of a solvent. The solvent used in the reaction includes, for example, water; ethers such as 1,4-dioxane, diethylether, tetrahydrofuran and tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane and chlorobenzene; hydrocarbons such as toluene, benzene and xylene; nitriles such as acetonitrile; aprotic polar solvents such as N, N- dimethylformamide, NMP, 1, 3-dimethyl-2-imidazolidinone and dimethyl sulfoxide; and mixtures thereof.
The amount of the compound (3) used in the reaction is usually from 1 to 2 mol per 1 mol of the compound (6) . The reaction is usually performed in the presence of a base. The base used in the reaction includes, for example, nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2, 6-lutidine, DBU and 1, 5-diazabicyclo [4, 3, 0] 5- nonene; tertiary amines such as triethylamine and N, N- diisopropylethylamine; and inorganic bases such as potassium carbonate and sodium hydride. The amount of the base used in the reaction is usually 1 mol or more per 1 mol of the compound ( 6) .
The reaction temperature of the reaction is usually within a range from -20 to 100°C. The reaction time of the reaction is usually within a range from 0.1 to 24 hours.
After completion of the reaction, the present compound
(1-i) can be isolated by pouring the reaction mixture into water followed by extraction with an organic solvent and subsequent concentration of the organic layer; pouring the reaction mixture into water followed by collection of the formed solid by filtration; or collecting a solid formed in the reaction mixture by filtration. The isolated present compound (1-i) can also be further purified by recrystallization, chromatography and so on.
The compound (6) includes, for example, the following pyrimidine compounds .
A pyrimidine compound represented by formula (6), wherein G1 is nitrogen.
A pyrimidine compound represented by formula (6), wherein Gl is CR6 and R1 is hydrogen.
A pyrimidine compound represented by formula (6), wherein R1 is hydrogen. A pyrimidine compound represented by formula (6), wherein R2 is hydrogen.
A pyrimidine compound represented by formula (6), wherein R1 and R2 are hydrogen.
A pyrimidine compound represented by formula (6), wherein G1 is nitrogen, and R1 and R2 are hydrogen.
A pyrimidine compound represented by formula (6), wherein R3 is hydrogen.
A pyrimidine compound represented by formula (6), wherein G1 is nitrogen and R3 is hydrogen.
A pyrimidine compound represented by formula (6), wherein G1 is CR6, R6 is hydrogen and R3 is hydrogen.
A pyrimidine compound represented by formula (6), wherein R4 is hydrogen, halogen, a nitro group, a cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, or -CC=O)R11.
A pyrimidine compound represented by formula (6), wherein R4 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, or -L2R10. a pyrimidine compound represented by formula (6), wherein R4 is halogen, a nitro group, a cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3- C8 cycloalkyl group optionally substituted with halogen, or -CC=O)R11.
A pyrimidine compound represented by formula (6), wherein R3 is hydrogen and R4 is hydrogen, halogen, a nitro group, A cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, -L2R10 or -CC=O)R11; A pyrimidine compound represented by formula (6), wherein R3 is hydrogen and R4 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or - L2 R1 0 .
A pyrimidine compound represented by formula (6), wherein R3 is hydrogen and R4 is halogen, a chain C1-C6 hydrocarbor group optionally substituted with halogen, or -L2R10. a pyrimidine compound represented by formula (6), wherein R3 is hydrogen and R4 is hydrogen, chlorine or a methyl group. A pyrimidine compound represented by formula (6), wherein G1 is nitrogen or CR6, R6 is hydrogen, R1 is hydrogen or halogen, R2 is hydrogen, halogen, or an amino group, and R4 is halogen, a nitro group, a cyano group, or a chain C1-C6 hydrocarbon group optionally substituted with halogen. A pyrimidine compound represented by formula (6), wherein G1 is nitrogen, R1 is hydrogen or halogen, R2 is hydrogen, halogen, or an amino group, R3 is hydrogen, and R4 is hydrogen, halogen, or a chain C1-C6 hydrocarbon group.
R4 is hydrogen, halogen, or a chain C1-C6 hydrocarbon group. A pyrimidine compound represented by formula (6), wherein G1 is nitrogen, R1 and R2 are hydrogen, R3 is hydrogen, and R4 is hydrogen, chlorine, or a methyl group.
(Production Process D)
The present compound (1-i) can be produced by reacting the compound represented by formula (7) :
Figure imgf000039_0001
wherein R1 , R2 , R3 , R4 , G1 and Q' are as defined above
(hereinafter referred to as the compound (7)) with the compound represented by formula (8) :
R5-L wherein R5 is as defined above, L represents a leaving group (chlorine, bromine, iodine, a paratoluenesulfonyloxy group, a methanesulfonyloxy group and so on) (hereinafter referred to as the compound (8) ) .
The reaction is performed in the presence or absence of a solvent. The solvent used in the reaction includes, for example, water; ethers such as 1,4-dioxane, diethylether, tetrahydrofuran and tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane and chlorobenzene; hydrocarbons such as toluene, benzene and xylene; nitriles such as acetonitrile; aprotic polar solvents such as N, N- dimethylformamide, NMP, 1, 3-dimethyl-2-imidazolidinone and dimethyl sulfoxide; and mixtures thereof.
The amount of the compound (8) used in the reaction is usually from 1 to 2 mol per 1 mol of the compound (7) . The reaction is usually performed in the presence of a base. The base used in the reaction includes, for example, nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2, 6-lutidine, DBU and 1, 5-diazabicyclo [4 , 3, 0] 5- nonene; tertiary amines such as triethylamine and N, N- diisopropylethylamine; and inorganic bases such as potassium carbonate and sodium hydride. The amount of the base used in the reaction is usually 1 mol or more per 1 mol of the compound (7 ) . The reaction temperature of the reaction is usually within a range from -20 to 100°C. The reaction time of the reaction is usually within a range from 0.1 to 24 hours.
After completion of the reaction, the present compound (1-i) can be isolated by pouring the reaction mixture into water followed by extraction with an organic solvent and subsequent concentration of the organic layer; ; pouring the reaction mixture into water followed by collection of the formed solid by filtration; or collecting a solid formed in the reaction mixture by filtration. The isolated present compound (1-i) can also be further purified by recrystallization, chromatography and so on.
The compound (7) includes, for example, the following pyrimidine compounds.
A pyrimidine compound represented by formula (7), wherein G1 is nitrogen.
A pyrimidine compound represented by formula (7), wherein G1 is CR6 and R6 is hydrogen. A pyrimidine compound represented by formula (7), wherein R1 is hydrogen.
A pyrimidine compound represented by formula (7), wherein R2 is hydrogen.
A pyrimidine compound represented by formula (7), wherein R1 and R2 are hydrogen.
A pyrimidine compound represented by formula (7), wherein G1 is nitrogen, and R1 and R2 are hydrogen.
A pyrimidine compound represented by formula (7), wherein R3 is hydrogen. A pyrimidine compound represented by formula (7), wherein G1 is nitrogen and R3 is hydrogen.
A pyrimidine compound represented by formula (7), wherein G1 is CR6, R6 is hydrogen and R3 is hydrogen. A pyrimidine compound represented by formula (7), wherein R4 is hydrogen, halogen, a nitro group, a cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, or -CC=O)R11. A pyrimidine compound represented by formula (7), wherein R4 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, or -L2R10. A pyrimidine compound represented by formula (7), wherein R4 is halogen, a nitro group, a cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3- C8 cycloalkyl group optionally substituted with halogen, or -C C=O)R11. A pyrimidine compound represented by formula (7), wherein R3 is hydrogen and R4 is hydrogen, halogen, a nitro group, A cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, -L2R10 or -CC=O)R11. A pyrimidine compound represented by formula (7), wherein R3 is hydrogen and R4 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or - L2R10.
A pyrimidine compound represented by formula (7), wherein R3 is hydrogen and R4 is halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L2R10. A pyrimidine compound represented by formula (7), wherein R3 is hydrogen and R4 is hydrogen, chlorine or a methyl group. A pyrimidine compound represented by formula (7), wherein Q' is oxygen, R3 is hydrogen and R4 is hydrogen, chlorine or a methyl group.
A pyrimidine compound represented by formula (7), wherein G1 is nitrogen, R1 and R2 are hydrogen, Q' is oxygen, R3 is hydrogen and R4 is hydrogen, chlorine or a methyl group.
(Production Process E)
Among the present compound, the compound represented by formula (1-ii) :
Figure imgf000043_0001
wherein R1, R2, R3, R4, R5 and G1 are as defined above, and Q" represents -S(O)- or -S(O)2- (hereinafter referred to as the present compound (1-ii)), the compound represented by formula (1-iii) :
Figure imgf000043_0002
wherein R1, R2, R3, R4, R5 and G1 are as defined above (hereinafter referred to as the compound (1-iii)), and an oxidizing agent.
Processes for producing intermediates in the production of the present compound will be described below.
(Reference Production Process 1)
The compound (2) can be produced by reacting the compound represented by formula (9):
Figure imgf000044_0001
wherein R3 and R4 are as defined above (hereinafter referred to as the compound (9)) with the compound represented by the compound (5) .
The reaction is performed in the presence or absence of a solvent. The solvent used in the reaction includes, for example, water; ethers such as 1,4-dioxane, diethylether, tetrahydrofuran and tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane and chlorobenzene; hydrocarbons such as toluene, benzene and xylene; nitriles such as acetonitrile; aprotic polar solvents such as N, N- dimethylformamide, NMP, 1, 3-dimethyl-2-imidazolidinone and dimethyl sulfoxide; and mixtures thereof.
The amount of the compound (5) used in the reaction is usually from 1 to 2 mol per 1 mol of the compound (9) .
The reaction is usually performed in the presence of a base. The base used in the reaction includes, for example, nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2, 6-lutidine, DBU and 1, 5-diazabicyclo [4, 3, 0] 5- nonene; tertiary amines such as triethylamine and N, N- diisopropylethylamine; and inorganic bases such as potassium carbonate and sodium hydride. The amount of the base used in the reaction is usually 1 mol or more per 1 mol of the compound ( 9) .
The reaction temperature of the reaction is usually within a range from -20 to 100°C. The reaction time of the reaction is usually within a range from 0.1 to 24 hours.
After completion of the reaction, the present compound (2) can be isolated by pouring the reaction mixture into water followed by extraction with an organic solvent and subsequent concentration of the organic layer; pouring the reaction mixture into water followed by collection of the formed solid by filtration; or collecting a solid formed in the reaction mixture by filtration. The isolated present compound (2) can also be further purified by recrystallization, chromatography and so on.
(Reference Production Process 2)
Among the compound (2), the compound represented by formula (2-i) :
Figure imgf000045_0001
wherein R1 , R3 and R4 are as defined above] (hereinafter referred to as the compound (2-i)) can be produced by reacting the compound represented by formula (10) :
Figure imgf000046_0001
wherein R3 and R4 are as defined above (hereinafter referred to as the compound (10)) with the compound represented by formula (11) :
H^OR14 wherein R14 represents a C1-C6 alkyl group optionally- substituted with halogen (hereinafter referred to as the compound (11) ) .
The reaction is performed in the presence or absence of a solvent. The solvent used in the reaction includes, for example, water; ethers such as 1,4-dioxane, diethylether, tetrahydrofuran and tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane and chlorobenzene; hydrocarbons such as toluene, benzene and xylene; nitriles such as acetonitrile; aprotic polar compounds such as N, N- dimethylformamide, NMP, 1, 3-dimethyl-2-imidazolidinone and dimethyl sulfoxide; and mixtures thereof.
The amount of the compound (11) used in the reaction is usually from 1 to 2 mol per 1 mol of the compound (10) . The reaction temperature of the reaction usually within a range from -20 to 1000C. The reaction time of the reaction is usually within a range from 0.1 to 24 hours. After the completion of the reaction, the compound (2- i) can be isolated by pouring the reaction mixture into water followed by extraction with an organic solvent and subsequent concentration of the organic layer. The isolated compound (2-i) can further purified by chromatography, distillation and so on.
(Reference Production Process 3)
The compound (10) can be produced by reacting the compound (9) with hydrazine.
The reaction is performed in the presence or absence of a solvent. The solvent used in the reaction includes, for example, water; ethers such as 1,4-dioxane, diethylether, tetrahydrofuran and tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane and chlorobenzene; hydrocarbons such as toluene, benzene and xylene; nitriles such as acetonitrile; aprotic polar compounds such as N, N- dimethylformamide, NMP, 1, 3-dimethyl-2-imidazolidinone and dimethyl sulfoxide; and mixtures thereof.
The hydrazine used in the reaction includes, for example, hydrazine and hydrazine hydrate.
The amount of the hydrazine used in the reaction is usually from 1 to 10 mol per 1 mol of the compound (9) .
The reaction is usually performed in the presence of a base. The base used in the reaction includes, for example, nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2, 6-lutidine, DBU and 1, 5-diazabicyclo [4 , 3, 0] 5- nonene; tertiary amines such as triethylamine and N, N- diisopropylethylamine; and inorganic bases such as potassium carbonate and sodium hydride. The amount of the base used in the reaction is usually 1 mol or more per 1 mol of the compound (9) .
The reaction temperature of the reaction is usually within a range from 0 to 100°C. The reaction time of the reaction is usually within a range from 0.1 to 24 hours. After the completion of the reaction, the compound (10) can be isolated by pouring the reaction, mixture into water followed by extraction with an organic solvent and subsequent concentration of the organic layer; pouring the reaction mixture into water followed by collection of the formed solid by filtration; or collecting a solid formed in the reaction mixture by filtration. The isolated compound (10) can further purified by chromatography, distillation and so on.
(Reference Production Process 4) The compound (4) can be produced by reacting the compound (9) with the compound (3) .
The reaction is performed in the presence or absence of a solvent. The solvent used in the reaction includes, for example, water; ethers such as 1,4-dioxane, diethylether, tetrahydrofuran and tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane and chlorobenzene; hydrocarbons such as toluene, benzene and xylene; nitriles such as acetonitrile; aprotic polar solvents such as N, N- dimethylformamide, NMP, 1, 3-dimethyl-2-imidazolidinone and dimethyl sulfoxide; and mixtures thereof.
The amount of the compound (3) used in the reaction is usually from 1 to 2 mol per 1 mol of the compound (9) .
The reaction is usually performed in the presence of a base. The base used in the reaction includes, for example, nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2, 6-lutidine, DBU and 1, 5-diazabicyclo [4, 3, 0] 5- nonene; tertiary amines such as triethylamine and N, N- diisopropylethylamine; and inorganic bases such as potassium carbonate and sodium hydride. The amount of the base used in the reaction is usually 1 mol or more per 1 mol of the compound ( 9 ) . The reaction temperature of the reaction is usually within a range from 0 to 100°C. The reaction time of the reaction is usually within a range from 0.1 to 24 hours.
After completion of the reaction, the present compound (4) can be isolated by pouring the reaction mixture into water followed by extraction with an organic solvent and subsequent concentration of the organic layer; pouring the reaction mixture into water followed by collection of the formed solid by filtration; or collecting a solid formed in the reaction mixture by filtration. The isolated present compound (4) can also be further purified by recrystallization, chromatography and so on.
(Reference Production Process 5)
The compound (6) can be produced by reacting the compound (9) with the compound (5).
The reaction is performed in the presence or absence of a solvent. The solvent used in the reaction includes, for example, water; ethers such as 1,4-dioxane, diethylether, tetrahydrofuran and tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane and chlorobenzene; hydrocarbons such as toluene, benzene and xylene; nitriles such as acetonitrile; aprotic polar solvents such as N, N- dimethylformamide, NMP, 1, 3-dimethyl-2-imidazolidinone and dimethyl sulfoxide; and mixtures thereof.
The amount of the compound (5) used in the reaction is usually from 2 to 3 mol per 1 mol of the compound (9) . The reaction is usually performed in the presence of a base. The base used in the reaction includes, for example, nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2, 6-lutidine, DBU and 1, 5-diazabicyclo [4 , 3, 0] 5- nonene; tertiary amines such as triethylamine and N, N- diisopropylethylamine; and inorganic bases such as potassium carbonate and sodium hydride. The amount of the base used in the reaction is usually 2 mol or more per 1 mol of the compound (9) .
The reaction temperature of the reaction is usually within a range from 0 to 100°C. The reaction time of the reaction is usually within a range from 0.1 to 24 hours.
After completion of the reaction, the present compound (6) can be isolated by pouring the reaction mixture into water followed by extraction with an organic solvent and subsequent concentration of the organic layer; pouring the reaction mixture into water followed by collection of the formed solid by filtration; or collecting a solid formed in the reaction mixture by filtration. The isolated present compound (6) can also be further purified by recrystallization, chromatography and so on.
(Reference Production Process 6)
Among the compound (7), the compound represented by formula (7-i) :
Figure imgf000051_0001
wherein R1 , R2 , R3 , R4 and G1 are as defined above
(hereinafter referred to as the compound (7-i) ) can be produced, for example, by subjecting the compound represented by formula (Y) :
Figure imgf000051_0002
wherein R1 , R2 , R3 , R4 and G1 are as defined above, to a hydrolysis reaction.
The reaction is usually performed in the presence of a base or an acid in water. An organic solvent may be added to the reaction. The organic solvent includes, for example, ethers such as 1,4-dioxane, diethylether, tetrahydrofuran, tert-butyl methyl ether and diglyme; hydrocarbons such as toluene, benzene and xylene; and nitriles such as acetonitrile.
The base used in the reaction includes, for example, inorganic bases such as potassium carbonate, sodium hydroxide, potassium hydroxide and sodium hydride; nitrogen- containing heterocyclic compounds such as pyridine, picoline, 2, 6-lutidine, DBU and 1, 5-diazabicyclo [4, 3, 0] 5-nonene; and tertiary amines such as triethylamine and N, N- diisopropylethylamine. When the reaction is performed in the presence of the base, the amount of the based used in the reaction is usually from 0.1 to 4 mol per 1 mol of the compound ( 6) .
The acid used in the reaction includes, for example, inorganic acids such as hydrochloric acid, bromic acid and sulfuric acid; and organic acids such as acetic acid and paratoluenesulfonic acid. When the reaction is performed in the presence of the acid, the amount of the acid used in the reaction is usually 0.1 mol or more per 1 mol of the compound (6) .
The reaction temperature of the reaction is usually within a range from 20 to 120°C. The reaction time of the reaction is usually within a range from 0.1 to 24 hours.
After the completion of the reaction, the compound (7) can be isolated by pouring the reaction mixture into water followed by extraction with an organic solvent and subsequent concentration of the organic layer; pouring the reaction mixture into water followed by collection of the formed solid by filtration; or collecting a solid formed in the reaction mixture by filtration. The isolated compound (7) can further purified by chromatography, distillation and so on.
(Reference Production Process 7)
Among the compound (7), the compound represented by formula (7-ii) :
Figure imgf000053_0001
wherein R1 , R2 , R3 , R4 and G1 are as defined above (hereinafter referred to as the compound (7-ii) ) can be produced by reacting the compound (7-i) with a sulfuration agent .
The reaction is performed in the presence or absence of a solvent. The solvent used in the reaction includes, for example, ethers such as 1,4-dioxane, diethylether, tetrahydrofuran, tert-butyl methyl ether and diglyme; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane and chlorobenzene; hydrocarbons such as toluene, benzene and xylene; nitriles such as acetonitrile; pyridines such as pyridine, picoline and lutidine; and mixtures thereof.
The sulfuration agent used in the reaction includes, for example, diphosphorus pentasulfide and Lawesson's reagent (2, 4-bis (4-methoxyphenyl) -1, 3-dithia-2, 4- diphosphetane 2, 4-disulfide) . The amount of the sulfuration agent used in the reaction is usually 1 mol or more per 1 mol of the compound (7-i) .
The reaction temperature of the reaction is usually within a range from 00C to 2000C. The reaction time of the reaction is usually within a range from 1 to 24 hours.
After completion of the reaction, the present compound (7-ii) can be isolated by pouring the reaction mixture into water followed by extraction with an organic solvent and subsequent concentration of the organic layer; or collecting a solid formed in the reaction mixture by filtration. The isolated present compound (7-ii) can also be further purified by recrystallization, chromatography and so on.
Specific examples of the present compound are the following.
A compound represented by formula (A) :
Figure imgf000054_0001
wherein R1 and R3 represent hydrogen, Q represents oxygen, and R2 , R5 , G1 and R6 represent combinations described in Table 1 to Table 6.
Figure imgf000055_0001
Figure imgf000056_0001
Figure imgf000057_0001
Figure imgf000058_0001
Figure imgf000059_0001
Figure imgf000060_0001
A compound represented by formula (B)
Figure imgf000061_0001
wherein R1 and R3 represent hydrogen, Q represents oxygen, and R2 , R5 , G1 and R6 represent combinations described in Table 1 to Table 6.
A compound represented by formula (C)
Figure imgf000061_0002
wherein R1 and R3 represent hydrogen, Q represents oxygen, and R2 , R5 , G1 and R6 represent any one of the combinations described in Table 1 to Table 6.
A compound represented by formula (D) :
Figure imgf000061_0003
wherein R1 and R3 represent hydrogen, Q represents oxygen, and R2 , R5 , G1 and R6 represent any one of the combinations described in Table 1 to Table 6.
A compound represented by formula (E) :
Figure imgf000062_0001
wherein R1 and R3 represent hydrogen, Q represents oxygen, and R2 , R5 , G1 and R6 represent any one of the combinations described in Table 1 to Table 6.
A compound represented by formula (F) :
Figure imgf000062_0002
wherein R1 and R3 represent hydrogen, Q represents oxygen, and R2 , R5 , G1 and R6 represent any one of the combinations described in Table 1 to Table 6.
A compound represented by formula (G)
Figure imgf000062_0003
wherein R1 and R3 represent hydrogen, Q represents oxygen, and R2 , R5 , G1 and R6 represent any one of the combinations described in Table 1 to Table 6.
A compound represented by formula (H) :
Figure imgf000063_0001
wherein R1 and R3 represent hydrogen, Q represents sulfur, and R2 , R5 , G1 and R6 represent any one of the combinations described in Table 1 to Table 6.
A compound represented by formula
Figure imgf000063_0002
wherein R1 and R3 represent hydrogen, Q represents sulfur, and R2 , R5 , G1 and R6 represent any one of the combinations described in Table 1 to Table 6. and
A compound represented by formula (J) :
Figure imgf000063_0003
wherein R1 and R3 represent hydrogen, Q represents sulfur, and R2 , R5 , G1 and R6 represent any one of the combinations described in Table 1 to Table 6.
Pests against which the present compound has an activity include, for example, noxious arthropods such as noxious insects and noxious acarines, and nematodes. Specific examples of these pests include the following.
Hemiptera: Planthoppers (Delphacidae) such as small brown planthopper (Laodelphax striatellus) , brown rice planthopper (Nilaparvata lugens), and white-backed rice planthopper (Sogatella furcifera) ; leafhoppers (Deltocephalidae) such as green rice leafhopper (Nephotettix cincticeps) , green rice leafhopper (Nephotettix virescens) , and tea green leafhopper (Empoasca onukii) ; aphids (Aphididae) such as cotton aphid (Aphis gossypii) , green peach aphid (Myzus persicae) , cabbage aphid (Brevicoryne brassicae) , piraea aphid (Aphis spiraecola) , potato aphid (Macrosiphum euphorbiae) , foxglove aphid (Aulacorthum solani) , oat bird-cherry aphid (Rhopalosiphum padi) , tropical citrus aphid (Toxoptera citricidus) , and mealy plum aphid (Hyalopterus pruni) ; stink bugs (Pentatomidae) such as green stink bug (Nezara antennata) , bean bug (Riptortus clavetus) , rice bug (Leptocorisa chinensis), white spotted spined bug
(Eysarcoris parvus), and stink bug (Halyomorpha mista) ; whiteflies (Aleyrodidae) such as greenhouse whitefly
(Trialeurodes vaporariorum) , sweetpotato whitefly (Bemisia tabaci) , citrus whitefly (Dialeurodes citri) , and citrus spiny white fly (Aleurocanthus spiniferus) ; scales (Coccidae) such as Calfornia red scale (Aonidiella aurantii) , San Jose scale (Comstockaspis perniciosa) , citrus north scale (Unaspis citri) , red wax scale (Ceroplastes rubens) , cottonycushion scale (Icerya purchasi) , Japanese mealybug (Planococcus kraunhiae) , Cosmstock mealybug (Pseudococcus longispinis) , and white peach scale (Pseudaulacaspis pentagona) ; lace bugs (Tingidae) ; cimices such as Cimex lectularius; psyllids (Psyllidae) .
Lepidoptera:
Pyralid moths (Pyralidae) such as rice stem borer (Chilo suppressalis) , yellow rice borer (Tryporyza incertulas) , rice leafroller (Cnaphalocrocis medinalis) , cotton leafroller (Notarcha derogata) , Indian meal moth
(Plodia interpunctella) , oriental corn borer (Ostrinia furnacalis) , cabbage webworm (Hellula undalis) , and bluegrass webworm (Pediasia teterrellus) ; owlet moths
(Noctuidae) such as common cutworm (Spodoptera litura) , beet armyworm (Spodoptera exigua) , armyworm (Pseudaletia separata) , cabbage armyworm (Mamestra brassicae) , black cutworm • (Agrotis ipsilon) , beet semi-looper (Plusia nigrisigna) , Thoricoplusia spp., Heliothis spp., and Helicoverpa spp.; white butterflies (Pieridae) such as common white (Pieris rapae) ; tortricid moths (Tortricidae) such as Adoxophyes spp., oriental fruit moth (Grapholita molesta) , soybean pod borer (Leguminivora glycinivorella) , azuki bean podworm (Matsumuraeses azukivora) , summer fruit tortrix (Adoxophyes orana fasciata) , smaller tea tortrix (Adoxophyes honmai.), oriental tea tortrix (Homona magnanima) , apple tortrix (Archips fuscocupreanus) , and codling moth (Cydia pomonella) ; leafblotch miners
(Gracillariidae) such as tea leafroller (Caloptilia theivora) , and apple leafminer (Phyllonorycter ringoneella) ; Carposinidae such as peach fruit moth (Carposina niponensis) ; lyonetiid moths (Lyonetiidae) such as Lyonetia spp.; tussock moths (Lymantriidae) such as Lymantria spp., and Euproctis spp.; yponomeutid moths (Yponomeutidae) such as diamondback (Plutella xylostella) ; gelechiid moths
(Gelechiidae) such as pink bollworm (Pectinophora gossypiella) , and potato tubeworm (Phthorimaea operculella) ; tiger moths and allies (Arctiidae) such as fall webworm
(Hyphantria cunea) ; tineid moths (Tineidae) such as casemaking clothes moth (Tinea translucens) , and webbing clothes moth (Tineola bisselliella) .
Thysanoptera :
Thrips (Thripidae) such as yellow citrus thrips (Frankliniella occidentalis) , melon thrips (Thrips palmi) , yellow tea thrips (Scirtothrips dorsalis) , onion thrips (Thrips tabaci) , flower thrips (Frankliniella intonsa) .
Diptera: Culices such as common mosquito (Culex pipiens pallens) , Cluex tritaeniorhynchus, and Cluex quinquefasciatus; Aedes spp. such as yellow fever mosquito (Aedes aegypti) , and Asian tiger mosquito (Aedes albopictus) ; Anopheles spp. such as Anopheles sinensis; chironomids (Chironomidae) ; house flies (Muscidae) such as Musca domestica, and Muscina stabulans; blow flies (Calliphoridae) ; flesh flies (Sarcophagidae) ; little house flies (Fanniidae) ; anthomyiid flies (Anthomyiidae) such as seedcorn fly (Delia platura) , and onion fly (Delia antiqua) ; leafminer flies (Agromyzidae) such as rice leafminer (Agromyza oryzae) , little rice leafminer (Hydrellia griseola) , tomato leafminer (Liriomyza sativae) , legume leafminer (Liriomyza trifolii) , and garden pea leafminer (Chromatomyia horticola) ; gout flies (Chloropidae) such as rice stem maggot (Chlorops oryzae) ; fruit flies (Tephritidae) such as melon fly (Dacus cucurbitae) , and Meditteranean fruit fly (Ceratitis capitata) ; Drosophilidae; humpbacked flies (Phoridae) such as Megaselia spiracularis; moth flies (Psychodidae) such as Clogmia albipunctata; Simuliidae; Tabanidae such as horsefly (Tabanus trigonus) ; stable flies.
Coleoptera:
Corn root worms (Diabrotica spp.) such as Western corn root worm (Diabrotica virgifera virgifera) , and Sourthern corn root worm (Diabrotica undecimpunctata howardi) ; scarabs (Scarabaeidae) such as cupreous chafer (Anomala cuprea) , soybean beetle (Anomala rufocuprea) , and Japanese beetle (Popillia japonica); weevils such as maize weevil (Sitophilus zeamais) , rice water weevil (Lissorhoptrus oryzophilus) , azuki bean weevil (Callosobruchus chinensis), rice curculio (Echinocnemus squameus) , boll weevil (Anthonomus grandis) , and hunting billbug (Sphenophorus venatus) ; darkling beetles (Tenebrionidae) such as yellow mealworm (Tenebrio molitor) , and red flour beetle (Tribolium castaneum) ; leaf beetles (Chrysomelidae) such as rice leaf beetle (Oulema oryzae) , cucurbit leaf beetle (Aulacophora femoralis) , striped flea beetle (Phyllotreta striolata) , and Colorado potato beetle (Leptinotarsa decemlineata) ; dermestid beetles (Dermestidae) such as varied carper beetle
(Anthrenus verbasci) , and hide beetle (Dermestes maculates) ; deathwatch beetles (Anobiidae) such as cigarette beetle
(Lasioderma serricorne) ; Epilachna such as Twenty-eight- spotted ladybird (Epilachna vigintioctopunctata) ; bark beetles (Scolytidae) such as powder-post beetle (Lyctus brunneus) , and pine shoot beetle (Tomicus piniperda) ; false powder-post beetles (Bostrychidae) ; spider beetles
(Ptinidae) ; longhorn beetles (Cerambycidae) such as white- spotted longicorn beetle (Anoplophora malasiaca) ; click beetles (Agriotes spp.); Paederus fuscipens .
Orthoptera:
Asiatic locust (Locusta migratoria) , African mole cricket (Gryllotalpa africana) , rice grasshopper (Oxya yezoensis) , rice grasshopper (Oxya japonica) , Gryllidae.
Hymenoptera:
Ants (Formicidae) such as pharaoh ant (Monomorium pharaosis) , negro ant (Formica fusca japonica), black house ant (Ochetellus glaber) , Pristomyrmex pungens, Pheidole noda, leaf-cutting ant (Acromyrmex spp.)/ and fire ant (Solenopsis spp.); hornets (Vespidae) ; bethylid wasps (Betylidae) ; sawflies (Tenthredinidae) such as cabbage sawfly (Athalia rosae) , and Athalia japonica.
Nematoda:
Aphelenchoides besseyi, Nothotylenchus acris, Meloidogyne incognita, Meloidogyne hapla, Meloidogyne javanica, Heterodera glycines, Globodera rostochiensis, Pratylenchus coffeae, Pratylenchus neglectus .
Blattodea: German cockroach (Blattella germanica) , smokybrown cockroach (Periplaneta fuliginosa) , American cockroach (Periplaneta americana) , Periplaneta brunnea, oriental cockroach (Blatta orientalis) ;
Acarina:
Spider mites (Tetranychidae) such as two-spotted spider mite (Tetranychus urticae) , Kanzawa spider mite (Tetranychus kanzawai) , citrus red mite (Panonychus citri) , European red mite (Panonychus ulmi) , and Oligonychus spp.; eriophyid mites (Eriophyidae) such as pink citrus rust mite (Aculops pelekassi) , Phyllocoptruta citri, tomato rust mite (Aculops lycopersici) , purple tea mite (Calacarus carinatus), pink tea rust mite (Acaphylla theavagran) , Eriophyes chibaensis, and apple rust mite (Aculus schlechtendali) ; tarosonemid mites (Tarsonemidae) such as broad mite (Polyphagotarsonemus latus) ; false spider mites (Tenuipalpidae) such as Brevipalpus phoenicis; Tuckerellidae; ticks (Ixodidae) such as Haemaphysalis longicornis, Haemaphysalis flava, Dermacentor taiwanicus, Ixodes ovatus, Ixodes persulcatus, black legged tick (Ixodes scapularis) , Boophilus microplus, and Rhipicephalus sanguineus; acarid mites (Acaridae) such as mold mite (Tyrophagus putrescentiae) , and Tyrophagus similis; house dust mites (Pyroglyphidae) such as Dermatophagoides farinae, and Dermatophagoides ptrenyssnus; cheyletide mites (Cheyletidae) such as Cheyletus eruditus,
Cheyletus malaccensis, and Cheyletus moorei; parasitoid mites (Dermanyssidae) such as tropical rat mite
(Ornithonyssus bacoti) , northern fowl mite (Ornithonyssus sylviarum) , and poultry red mite (Dermanyssus gallinae) ; chiggers (Trombiculidae) such as Leptotrombidium akamushi; spiders (Araneae) such as Japanese foliage spider
(Chiracanthium japonicum) , redback spider (Latrodectus hasseltii) .
The pest controlling agent of the present invention contains the present compound and an inert carrier. Generally, the pest controlling agent of the present invention is a formulation obtained by mixing the present compound and an inert carrier such as a solid carrier, a liquid carrier and a gaseous carrier, and further adding a surfactant and other adjuvant for formulation, if necessary. The formulation includes, for example, an emulsion, an oil solution, a powder, a granule, a wettable powder, a flowable formulation, a microcapsule, an aerosol, a smoking agent, a poison bait, and a resin formulation. In the pest controlling agent of the present invention, the present compound is usually contained in an amount of 0.01% to 95% by weight.
The solid carrier used for formulation includes, for example, a fine power and a granule of clays (e.g., kaolin clay, diatomite, bentonite, Fubasami clay, and acid clay) , synthetic hydrated silicon oxide, talc, ceramic, other inorganic minerals (e.g., sericite, quartz, sulfur, activated carbon, calcium carbonate, hydrated silica) or chemical fertilizers (e.g., ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, and ammonium chloride) .
The liquid carrier includes, for example, water, alcohols (e.g., methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, phenoxyethanol) , ketones (e.g., acetone, methyl ethyl ketone, cyclohexanone) , aromatic hydrocarbons (e.g., toluene, xylene, ethylbenzene, dodecylbenzene, phenylxylylethane, methylnaphthalene) , aliphatic hydrocarbons (e.g., hexane, cyclohexane, kerosine, light oil), esters (e.g., ethyl acetate, butyl acetate, isopropyl mylistate, ethyl oleate, diisopropyl adipate, diisobutyl adipate, propyleneglycol monomethyl ether acetate) , nitriles (e.g., acetonitrile, isobutyronitrile) , ethers (e.g., diisopropyl ether, 1,4-dioxane, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, 3-methoxy-3-methyl-l- butanol) , acid amides (e.g., N,N-dimethylformamide, N, N- dimethylacetamide) , halogenated hydrocarbons (e.g., dichloromethane, trichloroethane, tetrachlorocarbon) , sulfoxides (e.g., dimethylsulfoxide) , propylene carbonate, and vegetable oils (e.g., soy bean oil, cotton seed oil) .
The gaseous carrier includes, for example, fluorocarbons, butane gas, liquefied petroleum gas (LPG) , dimethyl ether, and carbon dioxide.
The surfactant includes, for example, nonionic surfactant, such as polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyethyleneglycol fatty acid ester; and anionic surfactant, such as alkylsulfonic acid salts, alkylbenzenesulfonic acid salts, alkylsurfic acid salts.
The other adjuvant for formulation includes, for example, binders, dispersants, colorants and stabilizers, and specifically for example, casein, gelatin, polysaccharides (e.g., starch, gum arabic, cellulose derivatives, alginic acid) , lignin derivatives, synthetic water-soluble polymers (e.g., polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acid), PAP (isopropyl acid phosphate), BHT (2, 6-di-t-butyl-4-methylphenol) , BHA (a mixture of 2-t-butyl-4-methoxyphenol and 3-t-butyl-4- methoxyphenol) .
The method for controlling pests of the present invention is applying an effective amount of the present compound to pests directly and/or habitats of pests (e.g., plant, soil, indoor, and in-body of animals) . The present compound is usually used as the pest controlling agent of the present invention for the method for controlling pests of the present invention.
When the pest controlling agent of the present invention is used for a control of pests in agriculture, the application amount is usually 1 to 10,000 g as the present compound per 10,000 m2. When the pest controlling agent of the present invention is a formulation of emulsions, wettable powders or flowables, they are usually applied after a dilution with water to have an active ingredient concentration of 0.01 to 10,000 ppm. When the pest controlling agent of the present invention is a formulation of granules or powders, they are usually applied as such.
These formulations and the dilute aqueous solution of the formulation may be sprayed directly to the plant to be protected from pests, and may be applied to the soil to control the pests living in a soil.
Furthermore, the resin formulations of sheets or strip form can be applied by a method such as winding around plants, stretching in the vicinity of plants and laying on the soil surface at the plant bottom.
When the pest controlling agent of the present invention is used for a control of pests in indoor, the application amount is usually 0.01 to 1,000 mg as the present compound per 1 m2 in case of application for plane surface, and 0.01 to 500 mg as the present compound per 1 m3 in case of application for space. When the pest controlling agent of the present invention is a formulation of emulsions, wettable powders or flowables, they are usually applied after a dilution with water to have an active ingredient concentration of 0.01 to 100,000 ppm. When the pest controlling agent of the present invention is a formulation of oil solutions, aerosols, smoking agents and poison baits, they are usually applied as such.
The pest controlling agent of the present invention could be used in farmlands on which "crops" shown below are cultivated.
"Crops"
Agricultural crops: corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, sarrazin, sugar beet, rapeseed, sunflower, sugar cane, tobacco;
Vegetables: Solanaceae vegetables (eggplant, tomato, green pepper, hot pepper, and potato) , Cucurbitaceae vegetables (cucumber, pumpkin, zucchini, watermelon, and melon ) , Cruciferae vegetables (Japanese radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, brown mustard, broccoli, and cauliflower) , Compositae vegetables (burdock, garland chrysanthemum, artichoke, and lettuce) , Liliaceae vegetables (Welsh onion, onion, garlic, and asparagus ) , Umbelliferae vegetables (carrot, parsley, celery, and parsnip), Chenopodiaceae vegetables (spinach, and Swiss chard) , Labiatae vegetables (Japanese basil, mint, and basil) , strawberry, sweat potato, yam, aroid;
Fruit trees: pomaceous fruits (apple, common pear, Japanese pear, Chinese quince, and quince) , stone fleshy fruits (peach, plum, nectarine, Japanese plum, cherry, apricot, and prune) , citrus plants (Satsuma mandarin, orange, lemon, lime, and grapefruit) , nuts (chestnut, walnut, hazel nut, almond, pistachio, cashew nut, and macadamia nut) , berry fruits (blueberry, cranberry, blackberry, and raspberry) , grape, persimmon, olive, loquat, banana, coffee, date, coconut palm, and oil palm;
Trees other fruit trees: tea, mulberry, flowering trees (azalea, japonica, hydrangea, sasanqua, lllicium anisatum, cherry tree, tulip poplar, crepe myetle, and orange osmanthus), street trees (ash tree, birch, dogwood, eucalyptus, ginkgo, lilac, maple tree, oak, poplar, cercis, Chinese sweet gum, plane tree, zelkova, Japanese arborvitae, fir tree, Japanese hemlock, needle juniper, pine, spruce, yew, elm, and horse-chestnut) , sweet viburnum, Podocarpus macrophyllus, Japanese cedar, Japanese cypress, croton, spindle tree, Chainese howthorn. N
Lawn: zoysia (Japanese lawn grass, mascarene grass) , Bermuda grass (Cynodon dactylon) , bent grass (creeping bent grass, Agrostis stolonifera, Agrostis tenuis) , bluegrass (Kentucky bluegrass, rough bluegrass) , fescue (tall fescue, chewing fescue, creeping fescue) , ryegrass (darnel, perennial ryegrass) , cocksfoot, timothy grass;
Others: flowers (rose, carnation, chrysanthemum, Eustoma grandiflorum Shinners (prairie gentian) , gypsophila, gerbera, pot marigold, salvia, petunia, verbena, tulip, aster, gentian, lily, pansy, cyclamen, orchid, lily of the valley, lavender, stock, ornamental kale, primula, poinsttia, gladiolus, cattleya, daisy, verbena, cymbidium, begonia) , biofuel plants (Jatropha, curcas, safflower, Camelina alyssum, switchgrass, miscanthus, reed canary grass, Arundo donax, kenaf, cassava, willow, algae), foliage plant.
The "crops" include genetically modified crops.
The pest controlling agents of the present invention can be a admixture with or together with other insecticides, acaricides, nematocides, fungicides, plant growth regulators, herbicides, and synergists.
Examples of active ingredients of the insecticide, the acaricide, the nematocide, the fungicide, the plant growth regulator, the herbicide, and the synergist are shown below.
Active ingredients of the insecticides:
(1) Organic phosphorus compounds: Acephate, Aluminium phosphide, butathiofos, cadusafos, chlorethoxyfos, chlorfenvinphos, chlorpyrifos, chlorpyrifos- methyl, cyanophos: CYAP, diazinon, DCIP (dichlorodiisopropyl ether), dichlofenthion: ECP, dichlorvos (DDVP), dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, etrimfos, fenthion: MPP, fenitrothion: MEP, fosthiazate, formothion, hydrogen phosphide, isofenphos, isoxathion, malathion, mesulfenfos, methidathion: DMTP, monocrotophos, naled: BRP, oxydeprofos: ESP, parathion, phosalone, phosmet: PMP, pirimiphos-methyl, pyridafenthion, quinalphos, phenthoate: PAP, profenofos, propaphos, prothiofos, pyraclorfos, salithion, sulprofos, tebupirimfos, temephos, tetrachlorvinphos, terbufos, thiometon, trichlorphon: DEP, vamidothion, phorate, cadusafos;
(2) Carbamate compounds: Alanycarb, bendiocarb, benfuracarb, BPMC, carbaryl, carbofuran, carbosulfan, cloethocarb, ethiofencarb, fenobucarb, fenothiocarb, fenoxycarb, furathiocarb, isoprocarb: MIPC, metolcarb, methomyl, methiocarb, NAC, oxamyl, pirimicarb, propoxur: PHC, XMC, thiodicarb, xylylcarb, aldicarb; (3) Pyrethroid compounds:
Acrinathrin, allethrin, benfluthrin, beta-cyfluthrin, bifenthrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin, deltamethrin, esfenvalerate, ethofenprox, fenpropathrin, fenvalerate, flucythrinate, flufenoprox, flumethrin, fluvalinate, halfenprox, imiprothrin, permethrin, prallethrin, pyrethrins, resmethrin, sigma-cypermethrin, silafluofen, tefluthrin, tralomethrin, transfluthrin, tetramethrin, phenothrin, cyphenothrin, alpha-cypermethrin, zeta-cypermethrin, lambda-cyhalothrin, gamma-cyhalothrin, furamethrin, tau-fluvalinate, metofluthrin, profluthrin, dimefluthrin, 2,3,5, 6-tetrafluoro-4- (methoxymethyl) benzyl (EZ) - (IRS, 3RS; IRS, 3SR) -2, 2-dimethyl-3-prop-l- enylcyclopropanecarboxylate, 2, 3, 5, 6-tetrafluoro-4- methylbenzyl (EZ) - (IRS, 3RS; IRS, 3SR) -2, 2-dimethyl-3-prop-l- enylcyclopropanecarboxylate, and 2, 3, 5, 6-tetrafluoro-4- (methoxymethyl) benzyl (IRS, 3RS; IRS, 3SR) -2, 2-dimethyl-3- (2- methyl-1-propenyl) cyclopropanecarboxylate; (4) Nereistoxin compounds:
Cartap, bensultap, thiocyclam, monosultap, bisultap; (5) Neonicotinoid compounds:
Imidacloprid, nitenpyram, acetamiprid, thiamethoxam, thiacloprid, dinotefuran, clothianidin; (6) Benzoylurea compounds:
Chlorfluazuron, bistrifluron, diafenthiuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, triazuron;
(7) Phenylpyrazole compounds:
Acetoprole, ethiprole, fipronil, vaniliprole, pyriprole, pyrafluprole;
(8) Bt toxins: Live spores derived from and crystal toxins produced from Bacillus thuringiesis and a mixture thereof;
(9) Hydrazine compounds:
Chromafenozide, halofenozide, methoxyfenozide, tebufenozide; (10) Organic chlorine compounds:
Aldrin, dieldrin, dienochlor, endosulfan, methoxychlor; (11) Other insecticidal active ingredients:
Machine oil, nicotine-sulfate; avermectin-B, bromopropylate, buprofezin, chlorphenapyr, cyantraniliprole, cyromazine, D-D (1, 3-Dichloropropene, emamectin-benzoate, fenazaquin, flupyrazofos, hydroprene, methoprene, indoxacarb, metoxadiazone, milbemycin-A, pymetrozine, pyridalyl, pyriproxyfen, spinosad, sulfluramid, tolfenpyrad, triazamate, flubendiamide, lepimectin, Arsenic acid, benclothiaz, Calcium cyanamide, Calcium polysulfide, chlordane, DDT, DSP, flufenerim, flonicamid, flurimfen, formetanate, metam- ammonium, metam-sodium, Methyl bromide, Potassium oleate, protrifenbute, spiromesifen, sulfoxaflor, Sulfur, metaflumizone, spirotetramat, pyrifluquinazone, spinetoram, chlorantraniliprole, tralopyril, cyantraniliprole, any compound represented by the following formula (K) :
Figure imgf000079_0001
wherein
R100 represents chlorine, bromine or a trifluoromethyl group,
R200 represents chlorine, bromine or a methyl group,
R300 represents chlorine, bromine or a cyano group and, any compound represented by the following formula (L) :
Figure imgf000079_0002
wherein
R1000 represents chlorine, bromine or iodide.
Active ingredients of the acardides:
Acequinocyl, amitraz, benzoximate, bifenaate, bromopropylate, chinomethionat, chlorobenzilate, CPCBS (chlorfenson) , clofentezine, cyflumetofen, dicofol, etoxazole, fenbutatin oxide, fenothiocarb, fenpyroximate, fluacrypyrim, fluproxyfen, hexythiazox, propargite: BPPS, polynactins, pyridaben, Pyrimidifen, tebufenpyrad, tetradifon, spirodiclofen, spiromesifen, spirotetramat , amidoflumet, cyenopyrafen.
Active ingredients of the nematocides : DCIP, fosthiazate, levamisol, methyisothiocyanate, morantel tartarate, imicyafos.
Active ingredients of the fungicides:
Azole fungicidal compounds such as propiconazole, prothioconazole, triadimenol, prochloraz, penconazole, tebuconazole, flusilazole, diniconazole, bromuconazole, epoxiconazole, difenoconazole, cyproconazole, metconazole, triflumizole, tetraconazole, myclobutanil, fenbuconazole, hexaconazole, fluquinconazole, triticonazole, bitertanol, imazalil, and flutriafol;
Cyclic amine fungicidal compouds such as fenpropimorph, tridemorph, and fenpropidin;
Benzimidazole fungicidal compounds such as carbendezim, benomyl, thiabendazole, and thiophanate-methyl; Procymidone; cyprodinil; pyrimethanil; diethofencarb; thiuram; fluazinam; mancozeb; iprodione; vinclozolin; chlorothalonil; captan; mepanipyrim; fenpiclonil; fludioxonil; dichlofluanid; folpet; kresoxim-methyl; azoxystrobin; trifloxystrobin; fluoxastrobin; picoxystrobin; pyraclostrobin; dimoxystrobin; pyribencarb; spiroxamine; quinoxyfen; fenhexamid; famoxadone; fenamidone; zoxamide; ethaboxam; amisulbrom; iprovalicarb; benthiavalicarb) ; cyazofamid; mandipropamid; boscalid; penthiopyrad; metrafenone; fluopiran; bixafen; cyflufenamid; proquinazid; isotianil, tiadinil.
Active ingredients of the herbicides:
(1) Phenoxyfatty acid herbicidal compounds 2,4-PA, MCP, MCPB, phenothiol, mecoprop, fluroxypyr, triclopyr, clomeprop, and naproanilide .
(2) Benzoic acid herbicidal compounds
2,3,6-TBA, dicamba, clopyralid, picloram, aminopyralid, quinclorac, and quinmerac. (3) Urea herbicidal compounds diuron, linuron, chlortoluron, isoproturon, fluometuron, isouron, tebuthiuron, methabenzthiazuron, cumyluron, daimuron, and methyl-daimuron.
(4) Triazine herbicidal compounds atrazine, ametoryn, cyanazine, simazine, propazine, simetryn, dimethametryn, prometryn, metribuzin, indaziflam, and triaziflam.
(5) Bipyridinium herbicidal compounds paraquat, and diquat. (6) Hydroxybenzonitrile herbicidal compounds bromoxynil and ioxynil.
(7) Dinitroaniline herbicidal compounds pendimethalin, prodiamine, and trifluralin.
(8) Organic phosphorus herbicidal compounds amiprofos-methyl, butamifos, bensulide, piperophos, anilofos, glyphosate, glufosinate, and bialaphos.
(9) Carbamate herbicidal compounds di-allate, tri-allate, EPTC, butylate, benthiocarb, esprocarb, molinate, dimepiperate, swep, chlorpropham, phenmedipham, phenisopham, pyributicarb, and asulam;
(10) Acid amide herbicidal compounds propanil, propyzamide, bromobutide, and etobenzanid.
(11) Chloroacetanilide herbicidal compounds acetochlor, alachlor, butachlor, dimethenamid, propachlor, metazachlor, metolachlor, pretilachlor, thenylchlor, and pethoxamid.
(12) Diphenylether herbicidal compounds acifluorfen-sodium, bifenox, oxyfluorfen, lactofen, fomesafen, chlomethoxynil, and aclonifen.
(13) Cyclic imide herbicidal compounds oxadiazon, cinidon-ethyl, carfentrazone-ethyl, surfentrazone, flumiclorac-pentyl, flumioxazin, pyraflufen- ethyl, oxadiargyl, pentoxazone, fluthiacet-methyl, butafenacil, benzfendizone, and saflufenacil .
(14) Pyrazole herbicidal compounds benzofenap, pyrazolate, pyrazoxyfen, topramezone, and pyrasulfotole .
(15) Triketone herbicidal compounds isoxaflutole, benzobicyclon, sulcotrione, mesotrione, tembotrione, and tefuryltrione.
(16) Aryloxyphenoxypropionic acid herbicidal compounds clodinafop-propargyl, cyhalofop-butyl, diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl, and quizalofop-ethyl and metamifol.
(17) Trioneoxime herbicidal compounds alloxydim-sodium, sethoxydim, butroxydim, clethodim, cloproxydim, cycloxydim, tepraloxydim, tralkoxydim, and profoxydim. (18) Sulfonylurea herbicidal compounds chlorsulfuron, sulfometuron-methyl, metsulfuron-methyl, chlorimuron-ethyl, tribenuron-methyl, triasulfuron, bensulfuron-methyl, thifensulfuron-methyl, pyrazosulfuron- ethyl, primisulfuron-methyl, nicosulfuron, amidosulfuron, cinosulfuron, imazosulfuron, rimsulfuron, halosulfuron- methyl, prosulfuron, ethametsulfuron-methyl, triflusulfuron- methyl, flazasulfuron, cyclosulfamuron, flupyrsulfuron, sulfosulfuron, azimsulfuron, ethoxysulfuron, oxasulfuron, iodosulfuron-methyl-sodium, foramsulfuron, mesosulfuron- methyl, trifloxysulfuron, tritosulfuron, orthosulfamuron, flucetosulfuron, and propyrisulfuron.
(19) Imidazolinone herbicidal compounds imazamethabenz-methyl, imazamethapyr, imazamox, imazapyr, imazaquin, and imazethapyr.
(20) Sulfonamide herbicidal compounds flumetsulam, metosulam, diclosulam, florasulam, cloransulam-methyl, penoxsulam, and pyroxsulam.
(21) Pyrimidinyloxybenzoic acid herbicidal compounds pyrithiobac-sodium, bispyribac-sodium, pyriminobac- methyl, pyribenzoxim, pyriftalid, and pyrimisulfan.
(22) Other herbicidal compounds
Bentazon, bromacil, terbacil, chlorthiamid, isoxaben, dinoseb, amitrole, cinmethylin, tridiphane, dalapon, diflufenzopyr-sodium, dithiopyr, thiazopyr, flucarbazone- sodium, propoxycarbazone-sodium, mefenacet, flufenacet, fentrazamide, cafenstrole, indanofan, oxaziclomefone, benfuresate, ACN, pyridate, chloridazon, norflurazon, flurtamone, diflufenican, picolinafen, beflubutamid, clomazone, amicarbazone, pinoxaden, pyraclonil, pyroxasulfone, thiencarbazone-methyl, aminocyclopyrachlor, ipfencarbazone, and methiozolin.
Active ingredients of the synergists:
Piperonyl butoxide, sesamex, sulfoxide, N- (2- ethylhexyl) -8, 9, 10-trinorborn-5-ene-2, 3-dicarboxyimide (MGK 264), N-declyimidazole, WARF-antiresistant, TBPT, TPP, IBP, PSCP, methyl iodide (CH3I), t-phenylbutenone, diethylmaleate, DMC, FDMC, ETP, and ETN.
Examples
The present invention will be described in more detail by way of Production Examples, Formulation Examples and Test Examples, but the present invention is not limited to these Examples .
First, Production Examples of the present compound are shown below. In the Production Examples, Ph represents a phenyl group and 2-ClPh represents a 2-chlorophenyl group.
Production Example 1
To a mixture of 27.6 g of 1, 2, 4-triazole, 100 mL of acetonitrile and 51.7 g of N, N-diisopropylethylamine, 14.9 g of 4, 6-dichloropyrimidine was added at room temperature.
The mixture was stirred at room temperature for 3 hours and then heated under reflux for 8 hours. After standing to cool, the reaction mixture was filtered and the filtrated substance was washed with acetonitrile and dried to obtain 13.8 g of 4, 6-bis ( [1, 2, 4 ] triazol-1-yl) -pyrimidine . 4, 6-bis ( [1,2,4] triazol-1-yl) -pyrimidine
Figure imgf000085_0001
1H-NMR (DMS0-D6)δ: 8. H(IH, d), 8.50(2H,s), 9.18(lH,d), 9.62 (2H,s) . To a mixture of 3.64 g of 2, 2, 3, 4 , 4, 4-hexafluoro-1- butanol and 20 mL of tetrahydrofuran, 0.81 g of sodium hydride (60% oily) was added under ice cooling, followed by stirring for 10 minutes. To the mixture, 4.28 g of 4,6- bis ( [1, 2, 4] triazol-1-yl) -pyrimidine was added, followed by stirring under ice cooling for 15 minutes and further stirring at room temperature for 2 hours. Water was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 5.17 g of 4- (2, 2, 3, 4, 4, 4- hexafluorobutyloxy) -6- ( [1,2,4] triazol-1-yl) -pyrimidine. 4- (2, 2, 3, 4, 4, 4-hexafluorobutyloxy) -6- ( [1,2, 4] triazol-1-yl) - pyrimidine <Compound 44>
Figure imgf000085_0002
Production Example 2
To a mixture of 11.1 g of 1, 2, 4-triazole, 20 mL of acetonitrile and 20.7 g of N, N-diisopropylethylamine, 7.34 g of 4 , 5, 6-trichloropyrimidine was added to room temperature. The mixture was stirred at room temperature for 2 hours. A solid was collected by filtering the reaction mixture. The solid was washed with acetonitrile and then dried to obtain 8.24 g of 5-chloro-4, 6-bis ( [1, 2, 4 ] triazol-1-yl) -pyrimidine . 5-chloro-4, 6-bis ( [1,2,4] triazol-1-yl) -pyrimidine
Figure imgf000086_0001
1H-NMR (CDCl3)δ: 8.26(2H,s), 8.98(lH,s), 9.12(2H,s) .
A mixture of 0.27 g of 5-chloro-4 , 6- bis ( [1,2, 4] triazol-1-yl) -pyrimidine, 2 mL of NMP, 0.15 g of DBU and 0.18 g of 2, 2, 3, 4, 4, 4-hexafluoro-1-butanol was stirred under ice cooling for 0.5 hour. An aqueous citric acid solution was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.20 g of 5-chloro-4- (2, 2, 3, 4, 4, 4-hexafluorobutyloxy) -6- ([1,2,4] triazol-1-yl) -pyrimidine. 5-chloro-4- (2,2,3, 4, 4, 4-hexafluorobutyloxy) -6- ( [1, 2, 4] triazol-1-yl) -pyrimidine <Compound 77>
Figure imgf000086_0002
Production Example 3 To a mixture of 8.29 g of 1, 2, 4-triazole, 50 mL of acetonitrile and 15.5 g of N, N-diisopropylethylamine, 6.70 g of 4 , 5, 6-trifluoropyrimidine was added dropwise at room temperature. The mixture was stirred at room temperature for 2 hours. A solid was collected by filtering the reaction mixture. The solid was washed subsequently with acetonitrile and water and then dried to obtain 8.95 g of 5- fluoro-4 ,6-bis( [l,2,4]triazol-l-yl) -pyrimidine. 5-fluoro-4 ,6-bis( [l,2,4]triazol-l-yl) -pyrimidine
Figure imgf000087_0001
1H-NMR (DMSO-D6)δ: 8.52(2H,s), 9.03(lH,s), 9.53(2H,s) . To a mixture of 0.46 g of 5-fluoro-4, 6- bis ( [1, 2, 4] triazol-1-yl) -pyrimidine, 4 iriL of NMP and 0.36 g of 2,2,3, 4, 4,4-hexafluoro-l-butanol, 0.30 g of DBU was added under ice cooling. The mixture was stirred under ice cooling for 0.5 hour. An aqueous citric acid solution was poured into the reaction mixture and the mixture was extracted with ethyl acetate. An aqueous citric acid solution was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.37 g of 5-fluoro-4- (2, 2, 3, 4, 4, 4-hexafluorobutyloxy) -6-
( [l,2,4]triazol-l-yl) -pyrimidine.
5-fluoro-4- (2,2,3,4,4, 4-hexafluorobutyloxy) -6- ( [1, 2, 4] triazol-1-yl) -pyrimidine <Compound 83>
Figure imgf000088_0001
Production Example 4
To a mixture of 9.0 g of 2, 2, 3, 4, 4, 4-hexafluoro-1- butanol and 50 mL of tetrahydrofuran, 2.0 g of sodium hydride (60% oily) was added under ice cooling, followed by stirring for 10 minutes. To the mixture, 7.45 g of 4,6- dichloropyrimidine was added, followed by stirring at room temperature for 1 day. Water was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 6.9 g of 6-chloro-4- (2, 2, 3, 4 , 4, 4-hexafluorobutyloxy) - pyrimidine.
6-chloro-4- (2,2,3,4,4, 4-hexafluorobutyloxy) -pyrimidine
Figure imgf000088_0002
1H-NMR (CDCl3)δ: 4.71-4.88 (2H,m) , 4.95-5.18 (IH, m) , 6.91-
6.93(lH,m), 8.62-8.64 (IH, m) . A mixture of 1.47 g of 6-chloro-4- (2, 2, 3, 4 , 4 , 4- hexafluorobutyloxy) -pyrimidine, 0.5 g of hydrazine monohydrate and 0.60 g of triethylamine was stirred at 70°C for 2 hours. The mixture was cooled to room temperature. Water was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The resultant crystal was collected by filtration and then dried to obtain 0.60 g of 4- (2, 2, 3, 4, 4, 4-hexafluorobutyloxy) -6-hydazinopyrimidine . 4-(2,2,3,4,4, 4-hexafluorobutyloxy) -6-hydazinopyrimidine
Figure imgf000089_0001
1H-NMR (CDCl3)O: 3.76(2H,s), 4.67-4.80 (2H,m) , 4.97-
5.21(lH,m) , 6.21(lH,s), 6.24(lH,s), 8.25(lH,s) .
To a mixture of 0.5 g of 4- (2, 2, 3, 4, 4, 4- hexafluorobutyloxy) -6-hydazinopyrimidine and 4 mL of acetonitrile, a mixture of 0.17 g of ethyl-N-cyano- formimidate and 2 mL of acetonitrile was added under ice cooling. The mixture was stirred at 50°C for 2 hours. Water was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 6.9 g of 6-{5-amino-[l,2, 4] triazol-1-yl }-4- (2,2, 3,4,4, 4- hexafluorobutyloxy) -pyrimidine. 6-{5-amino-[l,2,4]triazol-l-yl}-4-(2,2,3,4,4,4- hexafluorobutyloxy) -pyrimidine <Compound 87>
Figure imgf000089_0002
Production Example 5 To a mixture of 3.32 g of 1, 2, 4-triazole, 20 mL of acetonitrile and 6.20 g of N, N-diisopropylethylamine, 3.88 g of 4, 6-dichloro-5-nitropyrimidine was added at room temperature. The mixture was stirred at room temperature for 4 hours. The reaction mixture was filtered and the residue was washed with acetonitrile and dried to obtain
1.40 g of 5-nitro-4, 6-bis ( [1, 2, 4 ] triazol-1-yl) -pyrimidine. 5-nitro-4, 6-bis ( [1,2,4] triazol-1-yl) -pyrimidine
Figure imgf000090_0001
1H-NMR (DMSO-D6)δ: 8.51(2H,s), 9.33(lH,s), 9.71(2H,s). To a mixture of 1.04 g of 5-nitro-4,6- bis ( [1,2, 4] triazol-1-yl) -pyrimidine, 12 mL of NMP and 0.73 g of 2,2, 3, 4, 4, 4-hexafluoro-l-butanol, 0.61 g of DBU was added dropwise under ice cooling. The mixture was stirred under ice cooling for 0.5 hour. An aqueous citric acid solution was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.55 g of 4- (2,2,3,4,4,4-hexafluorobutyloxy) -5-nitro-6- ( [1,2, 4] triazol- 1-yl) -pyrimidine.
4- (2, 2, 3, 4, 4, 4-hexafluorobutyloxy) -5-nitro-6- ( [1, 2, 4] triazol-1-yl) -pyrimidine <Compound 90>
Figure imgf000090_0002
A mixture of 0 . 37 g of 4 - ( 2 , 2 , 3 , 4 , 4 , 4 - hexafluorobutyloxy) -5-nitro-6- ( [1,2,4] triazol-1-yl) - pyrimidine, 10 πiL of ethyl acetate and 10% Pd/C was stirred under a hydrogen atmosphere of about 1 atm at room temperature for 2 hours. The reaction mixture was filtered, and the filtrate was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.29 g of 5-amino-4- (2, 2, 3, 4, 4, 4-hexafluorobutyloxy) - 6- ( [1, 2, 4] triazol-1-yl) -pyrimidine. 5-amino-4- (2, 2,3,4,4, 4-hexafluorobutyloxy) -6- ( [1, 2, 4] triazol-1-yl) -pyrimidine <Compound 89>
Figure imgf000091_0001
Production Example 6 To a mixture of 2.65 g of 1, 2, 4-triazole, 10 mL of acetonitrile and 4.96 g of N, N-diisopropylethylamine, 2.61 g of 4, 6-dichloro-5-methylpyrimidine was added at room temperature. The mixture was heated under reflux for 14 hours. After standing to cool, a solid was collected by filtering the reaction mixture. The solid was washed with acetonitrile and then dried to obtain 2.12 g of 5-methyl- 4, 6-bis ( [1,2,4] triazol-1-yl) -pyrimidine. 5-methyl-4, 6-bis ( [1,2, 4]triazol-l-yl) -pyrimidine
Figure imgf000091_0002
1H-NMR (DMSO-D6)δ: 2.56(3H,s), 8.45(2H,s), 9. H(IH, s), 9 . 40 ( 2H , s ) .
To a mixture of 0.46 g of 5-methyl-4 , 6- bis ( [1,2,4] triazol-1-yl) -pyrimidine, 4 mL of NMP and 0.36 g of 2,2,3,4,4,4-hexafluoro-l-butanol, 0.30 g of DBU was added under ice cooling. The mixture was stirred for 1 hour. An aqueous citric acid solution was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.50 g of 4- (2, 2, 3, 4, 4, 4-hexafluorobutyloxy) -5- methyl-6- ( [l,2,4]triazol-l-yl) -pyrimidine . 4- (2, 2, 3, 4, 4, 4-hexafluorobutyloxy) -5-methyl-6- ( [1, 2, 4] triazol-1-yl) -pyrimidine <Compound 91>
Figure imgf000092_0001
Compound 91 can be also produced by the following method.
To the mixture of 5 g of 4,6-dichloro - 5- methylpyrimidine, 5.58 g of 2, 2, 3, 4 , 4, 4-hexafluorobuthanol and 30 mL NMP, 5.6 g of DBU was added under ice cooling. The mixture was stirred at room temperature for 1 day. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over magnesium salfate, and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 7.84 g of 4-chloro-6- (2, 2, 3, 4, 4, 4-hexafluorobuthoxy) -5- methylpyrimidine .
4-chloro-6- (2, 2,3,4,4, 4-hexafluorobuthoxy) -5- methylpyrimidine
Figure imgf000093_0001
1H-NMR(CDCl3) δ:2.29(3H, s ) , 4.74-4.87 (2H,m) , 4.92- 5.15 (IH, m) ,8.46(lH,s) .
The mixture of 0.62 g of 4-chloro-6- (2, 2, 3, 4, 4 , 4- hexafluorobuthoxy) -5-methylpyrimidine, 0.15 g of 1,2,4- triazol, 0.35 g of DBU and 3 mL of NMP was stirred at 50°C for 1 hour, at 100°C for 1 hour then 1300C for 6 hours.
Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.33 g of 4-
(2, 2, 3, 4, 4, 4-hexafluorobuthoxy) -5-methyl-6- ( [1,2, 4]triazol-
1-yl) -pyrimidine . <Compound 91>
To the mixture of 3.26 g of 4 , 6-dichloro-5- methylpyrimidine and 30 mL of tetrahydrofuran, 2.02 g of
1, 2, 4-triazol sodium salt was added under ice cooling. The mixture was stirred at room temperature for 3 hours, at 500C for 5 hours the 1300C for 7 hours. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure.
The residue was subjected to silica gel column chromatography to obtain 1.35 g of 4-chloro-5-methyl-6- ( [l,2,4]triazol-l-yl) -pyrimidine . 4-chloro-5-methyl-6- ( [l,2,4]triazol-l-yl) -pyrimidine
Figure imgf000094_0001
1H-NMR (CDCl3) δ: 2.76 (3H, s) , 8.17 ( IH, s) , 8.75 ( IH, s) , 9.14 ( IH, s) .
To the mixture of 0.39 g of 4-chloro-5-methyl-6- ( [1,2,4] triazol-1-yl) -pyrimidine, 0.36 g of 2,2,3,4,4,4- hexafluorobuthanol and 4 mL of NMP, 0.37 g DBU was added. The mixture was stirred at room temperature for 30 minutes. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.35g of 4- (2, 2, 3, 4, 4 , 4- hexafluorobuthoxy) -5-methy1-6- ( [1,2, 4] triazol-1-yl) - pyrimidine. <Compound 91>
Production Example 7
To a mixture of 4.14 g of 1, 2, 4-triazole, 30 mL of acetonitrile and 7.75 g of N,N-diisopropylethylamine, 3.41 g of 5-bromo-4, 6-dichloropyrimidine was added at room temperature. The mixture was stirred at room temperature for 8 hours. A solid was collected by filtering the reaction mixture. The solid was washed with acetonitrile and then dried to obtain 2.46 g of 5-bromo-4,6- bis ( [1,2,4] triazol-1-yl) -pyrimidine. 5-bromo-4, 6-bis ( [1,2, 4] triazol-1-yl) -pyrimidine
Figure imgf000095_0001
1H-NMR (DMSO-D6)δ: 8.47(2H,s), 9.26(lH,s), 9.35(2H,s).
To a mixture of 0.44 g of 5-bromo-4, 6- bis ( [1,2, 4] triazol-l-yl)-pyrimidine, 3 mL of NMP and 0.27 g of 2,2, 3, 4, 4, 4-hexafluoro-l-butanol, 0.23 g of DBU was added under ice cooling. An aqueous citric acid solution was poured into the reaction mixture. The mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.51 g of 5-bromo-4- (2,2, 3, 4, 4, 4-hexafluorobutyloxy) -6- ( [1, 2, 4 ] triazol-1-yl) - pyrimidine. 5-bromo-4- (2,2,3,4,4, 4-hexafluorobutyloxy) -6- ( [1,2, 4] triazol-1-yl) -pyrimidine <Compound 102>
Figure imgf000095_0002
Production Example 8
To a mixture of 27.6 g of 1, 2, 4-triazole, 50 mL of acetonitrile and 51.7 g of N, N-diisopropylethylamine, 16.3 g of 4 , 6-dichloro-2-methylpyrimidine was added at room temperature. The mixture was heated under reflux for 14 hours. A solid was collected by filtering the reaction mixture. The solid was washed with acetonitrile and then dried to obtain 20.3 g of 2-methyl-4, 6-bis ( [1, 2, 4] triazol-1- yl) -pyrimidine.
2-methyl-4, 6-bis ( [l,2,4]triazol-l-yl) -pyrimidine
Figure imgf000096_0001
1H-NMR (DMSO-D6)δ: 2.75(3H,s), 7.95 (IH, s) , 8.47(2H,s), 9.56(2H,s) .
To a mixture of 0.34 g of 2-methyl-4 , 6- bis ( [1,2, 4] triazol-1-yl) -pyrimidine, 3 mL of NMP and 0.27 g of 2,2,3,4,4, 4-hexafluoro-l-butanol, 0.23 g of DBU was added under ice cooling. The mixture was stirred at 60°C for 0.5 hour. After standing to cool, an aqueous citric acid solution was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.26 g of 4- (2, 2, 3, 4, 4, 4-hexafluorobutyloxy) -2-methyl-6- ( [1,2, 4] triazol-1-yl) -pyrimidine . 4- (2, 2, 3, 4, 4, 4-hexafluorobutyloxy) -2-methyl-6-
( [1, 2, 4 ] triazol-1-yl) -pyrimidine <Compound 106>
Figure imgf000096_0002
Production Example 9
A mixture of 3.48 g of 5-fluoro-4, 6- bis ( [1,2, 4] triazol-1-yl) -pyrimidine, 45 mL of NMP and 2.62 g of neopentylamine was stirred at room temperature for 6 hours. An aqueous citric acid solution was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. After pouring tert-butyl methyl ether into the residue and filtering the mixture, the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.41 g of 5-neopentylamino-4 , 6-bis ( [1, 2, 4 ] triazol-1-yl) - pyrimidine. 5-neopentylamino-4 , 6-bis ( [l,2,4]triazol-l-yl) -pyrimidine
Figure imgf000097_0001
1H-NMR (CDCl3 ) δ: 0.82 (9H, s) , 2.36 (2H,d) , 7.36 (lH, s) , 8.23 (2H, s) , 8.44 (lH, s) , 9.11 (2H, s) .
To a mixture of 0.30 g of 5-neopentylamino-4 , 6- bis ( [1, 2, 4 ] triazol-1-yl) -pyrimidine, 1 mL of NMP and 0.18 g of 2, 2, 3, 4, 4, 4-hexafluoro-l-butanol, 0.15 g of DBU was added under ice cooling. The mixture was stirred at room temperature for 12 hours. An aqueous citric acid solution was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.31 g of 4-
(2,2,3,4,4, 4-hexafluorobutyloxy) -5-neopentylamino-6- ( [1,2,4] triazol-1-yl) -pyrimidine .
4-(2,2,3,4,4, 4-hexafluorobutyloxy) -5-neopentylamino-6- ( [1, 2, 4] triazol-1-yl) -pyrimidine <Compound 112>
Figure imgf000098_0001
Production Example 10
To a mixture of 6.91 g of 1, 2, 4-triazole, 12.5 mL of acetonitrile and 12.9 g of N,N-diisopropylethylamine, 4.43 g of 4, 6-dichloro-5-ethylpyrimidine was added at room temperature. The mixture was heated under reflux for 11 hours. After standing to cool, the reaction mixture was concentrated under reduced pressure and a solid was collected by filtration. The solid was washed with acetonitrile and then dried to obtain 4.89 g of 5-ethyl-4,6- bis ( [1,2,4] triazol-1-yl) -pyrimidine.
5-ethyl-4, 6-bis ( [1,2, 4] triazol-1-yl) -pyrimidine
Figure imgf000098_0002
1H-NMR (CDCl3)O: 1.28(3H,t), 3.48(2H,q), 8.21(2H,s), 8.88(lH,s), 9.15(2H, s) . To a mixture of 0.48 g of 5-ethyl-4,6- bis ( [1, 2, 4] triazol-1-yl) -pyrimidine, 4 mL of NMP and 0.36 g of 2,2,3,4,4,4-hexafluoro-l-butanol, 0.30 g of DBU was added at room temperature. The mixture was stirred at room temperature for 2 hours. An aqueous citric acid solution was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.58 g of 5-ethyl-4- (2,2, 3,4,4,4-hexafluorobutyloxy) -6- ( [1, 2, 4] triazol-1-yl) - pyrimidine . 5-ethyl-4- (2,2, 3, 4, 4 , 4-hexafluorobutyloxy) -6-
( [1, 2, 4] triazol-1-yl) -pyrimidine <Compound 116>
Figure imgf000099_0001
Production Example 11 A mixture of 6.91 g of 1, 2, 4-triazole, 12.5 mL of acetonitrile, 12.9 g of N,N-diisopropylethylamine and 4.78 g of 4 , 6-dichloro-5-isopropylpyrimidine was heated under reflux for 18 hours. After standing to cool, the reaction mixture was concentrated under reduced pressure. A solid was collected by filtering the residue. The solid was washed with acetonitrile and then dried to obtain 4.41 g of 5-isopropyl-4, 6-bis( [1,2, 4] triazol-1-yl) -pyrimidine . 5-isopropyl-4, 6-bis ( [1,2,4] triazol-1-yl) -pyrimidine
Figure imgf000099_0002
1H-NMR (CDCl3 ) δ: 1.31 (6H,d) , 3.62-3.72 (IH, m) , 8.21 (2H, s) , 8.90 (lH, s) , 8.96 (2H, s) .
To a mixture of 0.51 g of 5-isopropyl-4, 6- bis ( [1, 2, 4] triazol-1-yl) -pyrimidine, 4 πiL of NMP and 0.36 g of 2,2,3, 4,4, 4-hexafluoro-l-butanol, 0.51 g of DBU was added at room temperature. The mixture was stirred overnight at room temperature. An aqueous citric acid solution was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.58 g of 5-isopropyl-4- (2,2,3,4,4,4-hexafluorobutyloxy) -6- ( [1,2, 4] triazol-1-yl) - pyrimidine . 5-isopropyl-4- (2,2,3,4,4, 4-hexafluorobutyloxy) -6- ( [1, 2, 4] triazol-1-yl) -pyrimidine <Compound 124>
Figure imgf000100_0001
Production Example 12 To a mixture of 0.86 g of 1, 2, 4-triazole, 6 mL of tetrahydrofuran and 1.90 g of DBU, 0.64 g of 5-tert-butyl- 4, 6-dichloropyrimidine was added at room temperature. The mixture was stirred at room temperature for 8 hours. The reaction mixture was concentrated under reduced pressure. To the residue, an aqueous citric acid solution was added and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.45 g of 5-tert-butyl-4 , 6-bis ( [1, 2, 4] triazol-1-yl) - pyrimidine . 5-tert-butyl-4, 6-bis ( [1,2,4] triazol-1-yl) -pyrimidine
Figure imgf000101_0001
1H-NMR (CDCl3)δ: 1.18(9H,s), 8.20(2H,s), 8.77(lH,s), 8.89(2H,s) . To a mixture of 0.23 g of 5-tert-butyl-4, 6- bis ( [1,2, 4] triazol-1-yl) -pyrimidine, 1.5 mL of NMP and 0.15 g of 2, 2, 3, 4, 4, 4-hexafluoro-1-butanol, 0.13 g of DBU was added at room temperature. The mixture was stirred overnight at room temperature. An aqueous citric acid solution was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.21 g of 5-tert-butyl-4- (2,2,3, 4, 4, 4-hexafluorobutyloxy) -6- ( [1,2, 4] triazol-1-yl) -pyrimidine .
5-tert-butyl-4- (2,2,3,4,4, 4-hexafluorobutyloxy) -6- ( [1, 2, 4 ] triazol-1-yl) -pyrimidine <Compound 129>
Figure imgf000102_0001
Production Example 13
To a mixture of 2.76 g of 1, 2, 4-triazole, 5 mL of acetonitrile and 1.79 g of 4, β-dichloro-5-methoxypyrimidine, 5.17 g of N, N-diisopropylethylamine was added at room temperature. The mixture was heated under reflux for 6 hours. After standing to cool, a solid was collected by filtering the reaction mixture. The solid was washed with acetonitrile and then dried to obtain 0.95 g of 5-methoxy- 4,6-bis( [l,2,4]triazol-l-yl) -pyrimidine. 5-methoxy-4, 6-bis ( [1,2,4] triazol-1-yl) -pyrimidine
Figure imgf000102_0002
1H-NMR (CDCl3)δ: 3.91(3H,s), 8.28(2H,s), 8.87(lH,s), 9.26(2H,s) .
To a mixture of 0.24 g of 5-methoxy-4, 6- bis ( [1,2,4] triazol-1-yl) -pyrimidine, 2 mL of NMP and 0.18 g of 2, 2, 3, 4, 4, 4-hexafluoro-l-butanol, 0.15 g of DBU was added at room temperature. The mixture was stirred at room temperature for 0.5 hour. An aqueous citric acid solution was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.19 g of 4-
(2,2,3,4,4, 4-hexafluorobutyloxy) -5-methoxy-6-
( [1,2,4] triazol-1-yl) -pyrimidine.
4-(2,2,3,4,4, 4-hexafluorobutyloxy) -5-methoxy-6-
( [1, 2, 4] triazol-1-yl) -pyrimidine <Compound 152>
Figure imgf000103_0001
Production Example 14 To 7.21 g of isobutylaldehyde, 7.31 g of tert- butylamine was added under ice cooling. The mixture was stirred at room temperature for 2 hours. To the reaction mixture, 100 mL of chloroform was added and the mixture was dried over sodium sulfate. To the resultant solution, N- 14.0 g of chlorosuccinimide was added under ice cooling, followed by stirring at room temperature for 5 hours. Water was poured into the reaction mixture and the mixture was extracted with chloroform. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. To the resultant residue, concentrated hydrochloric acid was added. The mixture was stirred at room temperature for 5 hours. To the reaction mixture, sodium hydrogen carbonate was added and the mixture was extracted with chloroform. The residue was distilled to obtain 3.90 g of 2-chloro-2-methylpropionaldehyde . 2-chloro-2-methylpropionaldehyde
Figure imgf000104_0001
1H-NMR (CDCl3)δ: 1.64(6H,s), 9.43(lH,s) .
To a mixture of 3.90 g of 2-chloro-2- methylpropionaldehyde and 37 mL of diethylether, 1.6 g of sodium borohydride was added. The mixture was stirred at room temperature for 5 hours. Water was poured into the reaction mixture and the mixture was extracted with diethylether. The organic layer was dried over sodium sulfate and the residue was distilled to obtain 1.0 g of 2- chloro-2-methylpropan-l-ol . 2-chloro-2-methylpropan-l-ol
Figure imgf000104_0002
1H-NMR (CDCl3)O: 1.57-1.59 (6H,m) , 1.98-2.06 (IH, m) , 3.55- 3.61 (2H,m) . To a mixture of 0.23 g of 5-methyl-4, 6- bis ( [1,2,4] triazol-1-yl) -pyrimidine, 3 mL of NMP and 0.19 g of 2-chloro-2-methylpropan-l-ol, 0.16 g of DBU was added under ice cooling. The mixture was stirred at 50°C for 5 hours. After standing to cool to room temperature, water was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.14 g of 4- (2-chloro-2- methylpropoxy) -5-methyl-6- ( [1,2, 4] triazol-1-yl) -pyrimidine . 4- ( 2-chloro-2-methylpropoxy) -5-methyl-6- ( [l,2,4]triazol-l- yl) -pyrimidine <Compound 156>
Figure imgf000105_0001
Production Example 15 To a mixture of 3.32 g of 1, 2, 4-triazole, 10 mL of acetonitrile and 4.50 g of 4 , β-dichloro-5-phenylpyrimidine, 6.20 g of N, N-diisopropylethylamine was added at room temperature. The mixture was heated under reflux for 13 hours. After standing to cool to room temperature, a solid was collected by filtering the reaction mixture. The solid was washed with acetonitrile and then dried to obtain 4.72 g of 5-phenyl-4, 6-bis ( [l,2,4]triazol-l-yl) -pyrimidine. 5-phenyl-4 ,6-bis( [l,2,4]triazol-l-yl) -pyrimidine
Figure imgf000105_0002
1H-NMR (CDCl3)O: 7.16-7.18 (2H,m) , 7.40-7.50 (3H,m) , 7.91(2H,s), 8.54(2H,s), 9.16(lH,s) .
To a mixture of 0.29 g of 5-phenyl-4 , 6- bis ( [1,2, 4] triazol-1-yl) -pyrimidine, 2 mL of NMP and 0.18 g of 2,2, 3, 4, 4, 4-hexafluoro-l-butanol, 0.15 g of DBU was added at room temperature. The mixture was stirred overnight at room temperature. An aqueous citric acid solution was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.26 g of 4-
(2, 2,3,4,4, 4-hexafluorobutyloxy) -5-phenyl-6- ( [1,2,4] triazol-
1-yl) -pyrimidine.
4-(2,2,3,4,4, 4-hexafluorobutyloxy) -5-phenyl-6-
( [1, 2, 4] triazol-1-yl) -pyrimidine <Compound 161>
Figure imgf000106_0001
Production Example 16 A mixture of 1.16 g of 1, 2, 4-triazole, 5 mL of acetonitrile and 1.81 g of 5- (2-chlorophenyl) -4 , 6- dichloropyrimidine was ice-cooled and 2.56 g of DBU was added. The mixture was stirred at room temperature for 0.5 hour. A solid was collected by filtering the reaction mixture. The solid was washed with acetonitrile and then dried to obtain 1.46 g of 5- (2-chlorophenyl) -4, 6- bis ( [1,2,4] triazol-1-yl) -pyrimidine. 5- (2-chlorophenyl) -4,6-bis( [l,2,4]triazol-l-yl) -pyrimidine
Figure imgf000106_0002
1H-NMR (CDCl3)δ: 7.12-7.14 (IH, m) , 7.27-7.29 (IH, m) , 7.39- 7.46(2H,m), 7.86(2H,s), 8.90(2H,s), 9.13(lH,s) .
To a mixture of 0.32 g of 5- (2-chlorophenyl) -4 , 6- bis ( [1,2, 4] triazol-1-yl) -pyrimidine, 2 mL of NMP and 0.18 g of 2, 2, 3, 4, 4, 4-hexafluoro-l-butanol, 0.15 g of DBU was added at room temperature. The mixture was stirred overnight at room temperature. An aqueous citric acid solution was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.32 g of 5-(2- chlorophenyl) -4- (2, 2,3,4,4, 4-hexafluorobutyloxy) -6- ( [1,2, 4] triazol-1-yl) -pyrimidine .
5- (2-chlorophenyl) -4- (2, 2, 3, 4, 4, 4-hexafluorobutyloxy) -6- ( [1, 2, 4] triazol-1-yl) -pyrimidine <Compound 163>
Figure imgf000107_0001
Production Example 17
To a mixture of 1.33 g of 1, 2, 4-triazole, 4 mL of acetonitrile and 1.39 g of 4 , 6-dichloro-5-cyanopyrimidine, 2.48 g of N,N-diisopropylethylamine was added dropwise under ice cooling. Under ice cooling, the mixture was allowed to stand for 1 hour. A solid was collected by filtering the reaction mixture. The solid was washed with acetonitrile and then dried to obtain 1.67 g of 5-cyano-4,6- bis( [l,2,4]triazol-l-yl) -pyrimidine . 5-cyano-4 , 6-bis ( [l,2,4]triazol-l-yl) -pyrimidine
Figure imgf000108_0001
1H-NMR (DMSO-D6)δ: 8.58(2H,s), 9.36(lH,s), 9.63(2H,s).
To a mixture of 0.24 g of 5-cyano-4,6- bis ( [1,2, 4]triazol-l-yl) -pyrimidine, 2 iτiL of NMP and 0.18 g of 2,2, 3, 4, 4, 4-hexafluoro-l-butanol, 0.15 g of DBU was added at -20°C. To the reaction mixture, an aqueous citric acid solution was added and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.21 g of 5-cyano-4- (2, 2, 3, 4, 4, 4- hexafluorobutyloxy) -6- ( [l,2,4]triazol-l-yl) -pyrimidine. 5-cyano-4- (2,2,3,4,4, 4-hexafluorobutyloxy) -6- ( [1, 2, 4] triazol-1-yl) -pyrimidine <Compound 165>
Figure imgf000108_0002
Production Example 18
To a mixture of 7.03 g of imidazole, 30 mL of tetrahydrofuran and 5.61 g of 4, 6-dichloro-5- methylpyrimidine, 15.7 g of DBU was added at room temperature. The mixture was stirred overnight. After reaction mixture was concentrated under reduced pressure, a solid was collected by filtration. The solid was washed with acetonitrile and then dried to obtain 1.93 g of 4,6- di (imidazol-1-yl) -5-methylpyrimidine. 4, 6-di (imidazol-1-yl) -5-methylpyrimidine
Figure imgf000109_0001
1H-NMR (CDCl3 ) δ: 2.54 (3H, s) , 7.27-7.28 (2H,m) , 7.55- 7.56 (2H,m) , 8.18-8.19 (2H,m) , 8.91 (lH, s) . To a mixture of 0.23 g of 4, 6-di (imidazol-1-yl) -5- methylpyrimidine, 2 mL of NMP and 0.18 g of 2,2,3,4,4,4- hexafluoro-1-butanol, 0.15 g of DBU was added at room temperature. The mixture was stirred overnight at room temperature. An aqueous citric acid solution was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.23 g of 4- (2, 2, 3, 4, 4, 4- hexafluorobutyloxy) -6- (imidazol-1-yl) -5-methylpyrimidine. 4- (2, 2, 3, 4, 4, 4-hexafluorobutyloxy) -6- (imidazol-1-yl) -5- methylpyrimidine <Compound 167>
Figure imgf000109_0002
Production Example 19
To a mixture of 4.09 g of imidazole, 10 mL of acetonitrile and 3.67 g of 4, 5, 6-trichloropyrimidine, 7.76 g of N, N-diisopropylethylamine was added under ice cooling. The mixture was allowed to stand overnight at room temperature. A solid was collected by filtering the reaction mixture. The solid was washed with acetonitrile and then dried to obtain 3.20 g of 5-chloro-4, 6-di (imidazol- 1-yl ) -pyrimidine . 5-chloro-4, 6-di (imidazol-1-yl) -pyrimidine
Figure imgf000110_0001
1H-NMR (CDCl3)δ: 7.26-7.27 (2H,m) , 7.83-7.84 (2H,m) , 8.49- 8.50 (2H,m) ,8.89(lH,s) .
To a mixture of 0.25 g of 5-chloro-4, 6-di (imidazol-1- yl) -pyrimidine, 2 mL of NMP and 0.18 g of 2,2,3,4,4,4- hexafluoro-1-butanol, 0.15 g of DBU was added under ice cooling. The mixture was stirred under ice cooling for 0.5 hour. An aqueous citric acid solution was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.21 g of 5-chloro-4- (2, 2, 3, 4, 4, 4- hexafluorobutyloxy) -6- (imidazol-1-yl) -pyrimidine. 5-chloro-4- (2,2,3,4,4, 4-hexafluorobutyloxy) -6- (imidazol-1- yl) -pyrimidine <Compound 169>
Figure imgf000110_0002
Production Example 20
To a mixture of 8.29 g of 1, 2, 4-triazole, 25 mL of acetonitrile and 15.5 g of N, N-diisopropylethylamine, 8.20 g of 2-amino-4, 6-dichloropyrimidine was added at room temperature. The mixture was heated under reflux for 6 hours. The reaction mixture was cooled to room temperature. A solid was collected by filtering the reaction mixture. The solid was washed subsequently with acetonitrile and tetrahydrofuran and then dried to obtain 3.86 g of 2-amino- 4-chloro-6- ( [1,2, 4]triazol-l-yl) -pyrimidine . 2-amino-4-chloro-6- ( [l,2,4]triazol-l-yl) -pyrimidine
Figure imgf000111_0001
1H-NMR (DMSO-D6 )δ: 7.01(lH,s), 7.60 (2H,brs) , 8.37(lH,s), 9.20 (IH, s) .
To a mixture of 0.98 g of 2-amino-4-chloro-6- ( [1,2, 4] triazol-1-yl) -pyrimidine, 5 mL of NMP and 0.91 g of 2, 2, 3, 4, 4, 4-hexafluoro-l-butanol, 0.24 g of 60% sodium hydride (oily) was added at room temperature. The mixture was stirred at 90°C for 3 hours. After standing to cool, an aqueous citric acid solution was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.11 g of 2-amino-4- (2, 2, 3, 4, 4 , 4-hexafluorobutyloxy) - 6- ( [1,2,4] triazol-1-yl) -pyrimidine. 2-amino-4- (2,2,3,4,4, 4-hexafluorobutyloxy) -6- ( [1,2,4] triazol-1-yl) -pyrimidine <Compound 190>
Figure imgf000112_0001
Production Example 21
A mixture of 2.3 g of 4, 6-bis ( [1, 2, 4 ] triazol-1-yl) - pyrimidine and 20 mL of concentrated hydrochloric acid was heated under reflux for 4 hours. The reaction mixture was cooled to room temperature. To the reaction mixture, sodium hydrogen carbonate was added. The precipitated crystal was collected by filtration. The crystal was dried to obtain 1.6 g of 6- ( [1, 2, 4] triazol-1-yl) -pyrimidin-4-ol. 6- ( [1,2,4] triazol-1-yl) -pyrimidin-4-ol
Figure imgf000112_0002
1H-NMR (DMSO-D6)δ: 6.59(lH,s), 8.34(lH,s), 8.38(lH,s), 9.28 (IH, s) .
A mixture of 1.63 g of 6- ( [1, 2, 4] triazol-1-yl) - pyrimidin-4-ol, 10 mL of 1,4-dioxane and 3.03 g of the Lawesson' s reagent was heated under reflux for 4 hours. After standing to cool, a solid was collected by filtering the reaction mixture. The solid was washed with 1,4-dioxane and then dried to obtain 1.63 g of 6- ( [1, 2, 4 ] triazol-1-yl) - pyrimidine-4-thiol . 6- ([1,2, 4] triazol-1-yl) -pyrimidine-4-thiol
Figure imgf000113_0001
1H-NMR (DMSO-D6)O: 7.45(lH,d), 8.40(lH,s), 8.48(lH,s),
9.36(lH,s), 14.40 (IH, brs) .
To a mixture of 0.54 g of 6- ( [1, 2, 4 ] triazol-1-yl) - pyrimidine-4-thiol, 3 mL of N,N-dimethylformamide and 0.94 g of 2, 2, 3, 4, 4, 4-hexafluoro-1-butyl trifluoromethanesulfonate, 0.50 g of potassium carbonate was added at room temperature. The mixture was stirred at room temperature for 2 hours. An aqueous citric acid solution was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.88 g of 4- (2, 2, 3, 4, 4, 4-hexafluorobutyl-1-sulfanyl) - 6-([l,2,4]triazol-l-yl) -pyrimidine.
4- (2, 2, 3, 4, 4, 4-hexafluorobutyl-1-sulfanyl) -6- ( [1, 2, 4 ] triazol-1-yl) -pyrimidine <Compound 191>
Figure imgf000113_0002
To a mixture of 0.55 g of 4- (2, 2, 3, 4, 4 , 4- hexafluorobutyl-1-sulfanyl) -6- ( [1, 2, 4 ] triazol-1-yl) - pyrimidine and 5 mL of chloroform, 0.49 g of m- chloroperbenzoic acid was added under ice cooling. The mixture was stirred overnight at room temperature. An aqueous sodium hydrogen carbonate solution was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was washed with a mixed solvent (2 : 1) of hexane and t-butyl methyl ether to obtain 0.42 g of 4- (2,2, 3, 4, 4, 4-hexafluorobutyl-1-sulfinyl) -6- ( [1,2,4] triazol-1-yl) -pyrimidine. 4- (2,2,3, 4, 4, 4-hexafluorobutyl-l-sulfinyl) -6- ( [1, 2, 4] triazol-1-yl) -pyrimidine <Compound 192>
Figure imgf000114_0001
To a mixture of 0.30 g of 4- (2, 2, 3, 4, 4, 4- hexafluorobutyl-1-sulfinyl) -6- ( [1, 2, 4 ] triazol-1-yl) - pyrimidine and 5 mL of chloroform, 0.25 g of m- chloroperbenzoic acid was added. The mixture was stirred at 600C for 8 hours. After standing to cool, an aqueous sodium hydrogen carbonate solution was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.18 g of 4- (2, 2, 3, 4 , 4, 4-hexafluorobutyl-1-sulfonyl) - 6- ( [1, 2, 4] triazol-1-yl) -pyrimidine. 4- (2,2,3,4,4, 4-hexafluorobutyl-1-sulfonyl) -6- ( [1, 2, 4 ] triazol-1-yl) -pyrimidine <Compound 193>
Figure imgf000114_0002
Production Example 22
To a mixture of 0.23 g of 4 , 6-di (imidazol-1-yl) -5- methylpyrimidine, 2 πiL of NMP and 0.10 g of (trimethylsilyl) methanol, 0.04 g of sodium hydride (60% oily) was added at room temperature. The mixture was stirred at room temperature for 1 hour. An aqueous citric acid solution was poured into the reaction mixture and the mixture was extracted with ethyl acetate twice. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.12 g of 6- (imidazol-1-yl) -5-methyl-4- { (trimethylsilyl ) methoxy Jpyrimidine. 6- (imidazol-1-yl) -5-methyl-4- { (trimethylsilyl) methoxy }pyrimidine <Compound 195>
Figure imgf000115_0001
Production Example 23
To a mixture of 0.23 g of 4, 6-di (imidazol-1-yl) -5- methylpyrimidine, 2 mL of NMP and 0.12 g of 2-
(trimethylsilyl) ethanol, 0.04 g of sodium hydride (60% oily) was added at room temperature. The mixture was stirred at room temperature for 1 hour. An aqueous citric acid solution was poured into the reaction mixture and the mixture was extracted with ethyl acetate twice. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.13 g of 6- (imidazol-1-yl) -5-methyl-4-{2- (trimethylsilyl) ethoxyjpyrimidine . 6- (imidazol-1-yl) -5-methyl-4-{2- (trimethylsilyl) ethoxy Jpyrimidine <Compound 196>
Figure imgf000116_0001
Production Example 24
A mixture of 4.56 g of 5-methyl-4, 6- bis ( [1, 2, 4 ] triazol-1-yl) -pyrimidine and 10 mL of concentrated hydrochloric acid was stirred at 700C for 4 hours. The reaction mixture was ice-cooled. To the reaction mixture, an aqueous 10% sodium hydroxide solution was added. The precipitated crystal was collected by filtration. The crystal was dried to obtain 3.04 g of 5- methyl-6- ( [l,2,4]triazol-l-yl) -pyrimidin-4-ol . 5-methyl-6- ( [1,2,4] triazol-1-yl) -pyrimidin-4-ol
Figure imgf000116_0002
1H-NMR (DMSO-D6)δ: 2.17 (3H,s), 8.24 (IH, s), 8.31 (IH, s) ,9.13(lH,s) , 12.94 (IH, brs) .
A mixture of 2.84 g of 5-methyl-6- ( [1, 2, 4 ] triazol-1- yl) -pyrimidin-4-ol, 15 mL of 1,4-dioxane and 3.24 g of the Lawesson's reagent was heated under reflux for 6 hours. After standing to cool, a solid was collected by filtering the reaction mixture. The solid was washed with 1,4-dioxane and then dried to obtain 2.24 g of 5-methyl-6-
( [1, 2,4] triazol-1-yl) -pyrimidine-4-thiol .
5-methyl-6- ( [1,2, 4] triazol-1-yl) -pyrimidine-4-thiol
Figure imgf000117_0001
1H-NMR (DMSO-D6)δ: 2.41(3H,s), 8.35(lH,s), 8.38(lH,s),
9.18(lH,s), 14.52 (IH, brs) .
To a mixture of 0.19 g of 5-methyl-6- ( [1, 2, 4] triazol- 1-yl) -pyrimidine-4-thiol, 1 mL of N,N-dimethylformamide and 0.31 g of 2,2, 3, 4, 4, 4-hexafluoro-1-butyl trifluoromethanesulfonate, 0.17 g of potassium carbonate was added under ice cooling. The mixture was stirred at room temperature for 1 hour. Water was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer washed subsequently with an aqueous citric acid solution and water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.27 g of 4- (2, 2, 3, 4 , 4 , 4-hexafluorobutyl-1-sulfanyl) -5-methyl-6- ( [1,2, 4] triazol-1-yl) -pyrimidine . 4- (2, 2, 3, 4, 4, 4-hexafluorobutyl-1-sulfanyl) -5-methyl-6- ( [1, 2, 4] triazol-1-yl) -pyrimidine <Compound 197>
Figure imgf000117_0002
Production Example 25 To a mixture of 0.19 g of 5-methyl-6- ( [1, 2, 4 ] triazol- 1-yl) -pyrimidine-4-thiol, 1 mL of N, N-dimethylformamide and 0.26 g of 2,2, 3, 3-tetrafluoro-1-propyl trifluoromethanesulfonate, 0.17 g of potassium carbonate was added under ice cooling. The mixture was stirred at room temperature for 1 hour. Water was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed subsequently with an aqueous citric acid solution and water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.21 g of 5-methyl-4- (2, 2, 3, 3-tetrafluoropropyl-1-sulfanyl) - 6- ( [1,2, 4]triazol-l-yl) -pyrimidine.
5-methyl-4- (2,2,3, 3-tetrafluoropropyl-1-sulfanyl) -6- ( [1, 2, 4] triazol-1-yl) -pyrimidine <Compound 198>
Figure imgf000118_0001
Production Example 26
To a mixture of 0.39 g of 5-methyl-6- ( [1, 2, 4] triazol- 1-yl) -pyrimidine-4-thiol, 5 mL of N, N-dimethylformamide and 0.03 g of potassium hydroxide, hexafluoropropene was added at room temperature. The mixture was stirred at 60°C for 1 hour. An aqueous citric acid solution was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.26 g of (Z) -5-methyl-4- (1,2,3,3, 3-pentafluoro-1-propenyl-l-sulfanyl) -6-
( [1, 2,4] triazol-1-yl) -pyrimidine .
(Z) -5-methyl-4- (1,2,3,3, 3-pentafluoro-l-propenyl-1- sulfanyl) -6- ( [1,2, 4] triazol-1-yl) -pyrimidine <Compound 222>
Figure imgf000119_0001
Production Example 27
A mixture of 0.35 g of 5-methyl-6- ( [1, 2, 4 ] triazol-1- yl) -pyrimidin-4-ol, 0.5 g of 1, 1, 1-trifluoro-5-iodopentane, 3 mL of NMP and 0.75 g of cesium carbonate was stirred at 80°C for 7 hours. Water was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed subsequently with saturated aqueous ammonium chloride solution and water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.05 g of 4- (5,5,5- trifluoropentyloxy) -5-methyl-6- ( [1,2,4] triazol-1-yl) - pyrimidine . 4- (5, 5, 5-trifluoropentyloxy) -5-methyl-6- ([1,2, 4] triazol-1- yl) -pyrimidine <Compound 219>
Figure imgf000119_0002
Production Example 28 Under a nitrogen atmosphere, to a mixture of 10.9 g of 1, 1, 1, 3, 3, 3-hexafluoro-2-propanol and 50 inL of tetrahydrofuran, 8.4 mL of butyllithium (1.6 M) was added at 00C. The mixture was stirred at 0°C for 2 hours. To the mixture, 19.5 g of paraformaldehyde was added, followed by stirring at room temperature for 10 hours. To the reaction mixture, 100 mL of water and 3.7 g of sodium borohydride were added. The mixture was stirred at room temperature for 1 day. To the reaction mixture, 20 mL of 20% hydrochloric acid was added and the mixture was extracted with ethyl acetate. The organic layer was concentrated under reduced pressure. The residue was distilled under reduced pressure to obtain 7 g of 2, 2, 2, 4 , 4-pentafluoro-1, 3-butanediol . 2,2,2,4, 4-pentafluoro-1, 3-butanediol
Figure imgf000120_0001
To a mixture of 0.46 g of 5-methyl-4, 6- bis ( [1, 2, 4 ] triazol-1-yl) -pyrimidine, 3 mL of NMP and 0.36 g of 2, 2, 2, 4, 4-pentafluoro-1, 3-butanediol, 0.40 g of DBU was added under ice cooling. The mixture was stirred at room temperature for 5 hours. Water was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed subsequently with saturated aqueous ammonium chloride solution and water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.30 g of 4- (3-hydroxy-2, 2, 4, 4, 4- pentafluorobutyloxy) -5-methyl-6- ( [1,2,4] triazol-1-yl) - pyrimidine.
4- (3-hydroxy-2,2, 4,4, 4-pentafluorobutyloxy) -5-methyl-6-
( [1, 2, 4] triazol-1-yl) -pyrimidine <Compound 226>
Figure imgf000121_0001
Production Example 29
To a mixture of 0.17 g of 4- (3-hydroxy-2, 2, 4 , 4 , 4- pentafluorobutyloxy) -5-methyl-6- ( [l,2,4]triazol-l-yl)- pyrimidine and 3 mL of tetrahydrofuran, 0.03 g of sodium hydride (60% oily) and 0.08 g of methyl iodide were added at 00C. The mixture was stirred at room temperature for 30 minutes. Water was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and then concentrated under reduced pressure to obtain 0.18 g of 4- (2, 2, 4, 4, 4- pentafluoro-3-methoxy-butyloxy) -5-methyl-6- ( [l,2,4]triazol- 1-yl) -pyrimidine <Compound 227>.
Figure imgf000121_0002
Production Example 30
A mixture of 0.68 g of 4- (3-hydroxy-2, 2, 4, 4 , 4- pentafluorobutyloxy) -5-methyl-6- ( [l,2,4]triazol-l-yl)- pyrimidine and 3 mL of tetrahydrofuran was cooled to 00C, and 0.03 g of sodium hydride and 0.38 g of phenyl chlorothiocarbonate were added. The mixture was stirred at room temperature for 30 minutes. Water was poured into the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.82 g of the compound represented by formula (Z).
Figure imgf000122_0001
A mixture of 0.82 g of the compound represented by formula (Z), 0.58 g of tributyltin hydride, 0.07 g of azodiisobutyronitrile and 5 mL of toluene was stirred at 80°C for 1 hour and then stirred at 1100C for 1 hour. Water was poured into the reaction mixture and the mixture was extracted with ethyl acetate, dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.46 g of 4- (2, 2, 4, 4, 4-pentafluorobutyloxy) -5-methyl-6- ( [l,2,4]triazol-l-yl) -pyrimidine . 4- (2, 2, 4, 4, 4-pentafluorobutyloxy) -5-methyl-6- ( [1,2, 4] triazol-1-yl) -pyrimidine <Compound 228>
Figure imgf000122_0002
Production Example 31
To a mixture of 7.0 g of 1, 2, 4-triazol and 100 mL of tetrahydrofuran, 4g of 60% sodium hydride (in oil) was added with ice cooling. The mixture was stirred for 15 minutes with ice cooling . Fourteen point nine gram of 4,6- dichloropyrimidine was added hereto, and stirred at room temperature for 1 hour then at 70°C for 6hours. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 7.0 g of 4-chloro-6- ( [1,2,4] triazol-1-yl) -pyrimidine. 4-chloro-6-([l,2,4]triazol-l-yl) -pyrimidine
Figure imgf000123_0001
1H-NMR(CDCl3)OrV.93 (IH, s) , 8.17 (IH, s) , 8.89 (IH, s) , 9.23 (IH, s) . To a mixture of 0.25 g of 2,2- bis (trifluoromethyl) propanol and 4 mL of tetrahydrofuran, 0.06 g of 60% sodium hydride (in oil) was added. The mixture was stirred for 20 minutes. Zero point two five gram of 4-chloro-6- ( [1, 2, 4 ] triazol-1-yl) -pyrimidine was added hereto and stirred at room temperature for 1 day. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.18 g of 4- ( [1,2,4] triazol-1-yl) -6- [2, 2-bis (trifluoromethyl) propoxy] - pyrimidine. <Compound 11>
Figure imgf000124_0001
Production Example 32
To a mixture of 5 g of 4, 6-dichloropyrimidine, 4.43 g of 2, 2, 3, 3-tetrafluoropropanol and 70m L of tetrahydrofuran,
1.4 g of 60% sodium hydride (in oil) was added. The mixture was stirred for 1 hour at room temperature. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 8.1 g of 4-chloro-6-
(2,2,3, 3-tetrafluoropropoxy) -pyrimidine .
4-chloro-6- (2,2,3, 3-tetrafluoropropoxy) -pyrimidine
F N^N
F F
1H-NMR(CDCl3)O: 4.83 (2H,tt) , 5.96 (IH, tt ) , 6.92 (IH, s) , 8.62 ( IH, s) .
The mixture of 0.49 g of 4-chloro-6- (2, 2, 3, 3- tetrafluoropropoxy) -pyrimidine, 0.15 g of 1, 2, 4-triazol, 0.37 g of DBU and 3 mL of NMP was stirred at 50°C for 1 hour then at 80°C for 1 hour. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.39 g of 4- (2, 2, 3, 3-tetrafluoropropoxy) -6- ( [1, 2, 4] triazol-1-yl) -pyrimidine . <Compound 22>
Figure imgf000125_0001
Compound 22 can be also produced by the following method. To the mixture of 0.36 g of 4-chloro-6- ( [1, 2, 4] triazol- 1-yl) -pyrimidine, 0.24 g of 2, 2, 3, 3-tetrafluoropropanol and 4 mL NMP, 0.37 g of DBU was added. The mixture was stirred at room temperature for 30 minutes. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.33 g of 4- (2, 2,3,3- tetrafluoropropoxy) -6- ( [1,2,4] triazol-1-yl) -pyrimidine. <Compound 22>
Production Example 33
To the mixture of 0.5 g of 5-chloro-4, 6- bis ( [1,2, 4] triazol-1-yl) -pyrimidine, 5 mL of NMP and 0.46 g of 2,2,3, 3,4, 4, 5, 5-octafluoropentanol, 0.35 g of DBU was added under ice cooling. The mixture was stirred at room temperature for 1 hour. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.68 g of5-chloro-4- (2, 2, 3, 3, 4 , 4, 5, 5- octafluoropentyloxy) -6- ( [l,2,4]triazol-l-yl) -pyrimidine . 5-chloro-4- (2,2,3,3,4,4,5, 5-octafluoropentyloxy) -6- ( [1, 2, 4] triazol-1-yl) -pyrimidine <Compound 121>
Figure imgf000126_0001
Production Example 34
To the mixture of 0.46g of 5-methyl-4 , 6- bis ( [1, 2, 4] triazol-1-yl) -pyrimidine, 3 mL of NMP and 0.46 g of 2, 2, 3, 3, 4, 4, 5, 5-octafluoropentanol, 0.33g of DBU was added. The mixture was stirred at room temperature for 1 hour. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.68 g of 5-methyl-4- (2, 2, 3, 3, 4, 4, 5, 5-octafluoropentyloxy) -6- ( [1,2, 4] triazol-1-yl) -pyrimidine .
5-methyl-4- (2,2,3,3,4,4,5, 5-octafluorpentyloxy) -6- ( [1, 2, 4] triazol-1-yl) -pyrimidine <Compound 133>
Figure imgf000126_0002
Production Example 35
To the mixture of 0.46g of 5-methyl-4 , 6- bis ( [1,2, 4] triazol-1-yl) -pyrimidine, 3 mL of NMP and 0.25 g ethyleneglycol mono-tert-butyl ether, 0.33 g of DBU was added. The mixture was stirred at room temperature. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.68g of 5-methyl-4- (2- tert-buthoxyethoxy) -6- ( [l,2,4]triazol-l-yl) -pyrimidine. 5-methyl-4- (2-tert-buthoxyethoxy) -6- ( [1,2, 4 ] triazol-1-yl) - pyrimidine <Compound 135>
Figure imgf000127_0001
The compounds produced by the production methods described in the Production Examples are shown below.
Figure imgf000127_0002
wherein R1 , R2 , R3 , R4 , R5 , G1 , R6 and Q represent combinations described Table 7 to Table 14 shown below.
Figure imgf000128_0001
Table 8
Figure imgf000129_0001
Figure imgf000130_0001
Figure imgf000130_0002
Figure imgf000131_0001
Figure imgf000132_0001
Figure imgf000133_0001
Figure imgf000134_0001
Figure imgf000135_0001
Figure imgf000136_0001
Figure imgf000137_0001
1H-NMR data of the compound of the present invention described in Table 7 to Table 14 is shown in the following. Compound 1
1H-NMR(CDCl3) δ: 2.23(3H,s), 2.91(2H,t), 4.64(2H,t), 7.24(lH,d), 8.12(1H, s), 8.65(lH,d), 9.18(lH,s) .
Compound 2
1H-NMR(CDCl3) δ: 1.00(3H,t), 1.41(6H,s), 1.53-1.65 (2H,m) ,
2.60(2H,t), 4.41(2H,s), 7.27(lH,d), 8.12(lH,s), 8.64(lH,d), 9.18 (IH, s) .
Compound 3
1H-NMR(CDCl3) δ: 1.40(6H,s), 2.12-2.14 (3H,m) , 4.41(2H,s),
7.27(lH,s), 8.12(lH,s), 8.64(lH,s), 9.18(lH,s).
Compound 5 1H-NMR(CDCl3) δ: 1.54(6H,s), 3.02(3H,s), 4.69(2H,s),
7.26(lH,s), 8.13(1H, s), 8.69(lH,s), 9.20(lH,s) .
Compound 6
1H-NMR(CDCl3) δ: 1.73(3H,d), 6. H(IH, q), 7.36(lH,d),
8.13(1H, s), 8.68(lH,d), 9.19(lH,s) . Compound 7
1H-NMR(CDCl3) δ: 1.69-1.75 ( 3H,m) , 6.07-6.14 ( IH, m) ,
6.79(lH,s), 7.21-7.23(lH,m) , 7.59-7.64 (lH,m) , 8.43-
8.46(lH,m) , 8.68 (IH, s) .
Compound 8 1H-NMR(CDCl3) δ: 5.17(2H,s), 7.43(lH,d), 8.14(lH,s),
8.69(lH,s), 9.20(lH,s) .
Compound 9
1H-NMR(CDCl3) δ: 5.15-5.17 (2H,m) , 6.86-6.88 (IH, m) , 7.22-
7.24(lH,m), 7.62-7.65 (IH, m) , 8.45-8.47 (IH, m) , 8.68- 8.69(lH,m) .
Compound 10
1H-NMR(CDCl3) δ: 4.90(2H,q), 7.38(lH,d), 8.14(lH,s),
8.69(lH,d), 9.20(lH,s) .
Compound 11 1H-NMR(CDCl3) δ: 1.54(3H,s), 4.77(2H,s), 7.31(lH,s),
8.13(1H, s), 8.68(lH,s), 9.19(lH,s) .
Compound 12
1H-NMR(CDCl3) δ: 1.65-1.82 (3H,m) , 1.87-1.89 (2H,m) , 3.28(2H,t), 3.74(2H,s), 7.71(lH,d), 8.12(lH,s), 8.79(lH,d),
9.20(lH,s) .
Compound 13
1H-NMR(CDCl3) δ: 1.25(6H,s), 2.00-2.04 (2H,m) , 3.24(3H,s),
4.53-4.57 (2H,m) , 7.19(lH,d), 8.12(lH,s), 8.65(lH,d), 9.18(1H, s) .
Compound 14
1H-NMR(CDCl3) δ: 1.25(6H,s), 1.99-2.03 (2H,m) , 3.24(3H,s),
4.52-4.56(2H,m) , 6.63(lH,d), 7.20-7.21 (IH, m) , 7.60-
7.61(lH,m), 8.41-8.42 (IH, m) , 8.65(lH,d) . Compound 15
1H-NMR(CDCl3) δ: 1.23(9H,s), 3.74(2H,t), 4.55(2H,t),
7.26(lH,d), 8.12(1H, s), 8.64(lH,d), 9.18(lH,s) .
Compound 16
1H-NMR(CDCl3) δ: 1.23(9H,s), 3.73(2H,t), 4.55(2H,t), 6.71(lH,s), 7.21(lH,s), 7.60(lH,s), 8.41(lH,s), 8.64(lH,s) .
Compound 17
1H-NMR(CDCl3) δ: 5.34(2H,s), 7.46(lH,d), 8.14(lH,s),
8.69(lH,d), 9.21(lH,s) .
Compound 18 1H-NMR(CDCl3) δ: 5.33(2H,s), 6.89(lH,d), 7.23-7.25 (IH, m) ,
7.64-7.65(lH,m) , 8.46-8.47 (IH, m) , 8.69(lH,d) .
Compound 19
1H-NMR(CDCl3) δ: 1.80(6H,s), 7.18(lH,d), 8.03(lH,s),
8.55(lH,d), 9.1O(1H, s) . Compound 20
1H-NMR(CDCl3) δ: 1.14(6H,s), 3.55(2H,s), 4.28(2H,s),
7.25(lH,d), 8.12(1H, s), 8.65(lH,d), 9.18(lH,s) .
Compound 21 1H-NMR(CDCl3) δ: 1.14(6H,s), 3.55(2H,s), 4.28(2H,s),
6.69(lH,d), 7.21-7.22 (IH, m) , 7.61-7.62 (IH, m) , 8.42-
8.43 (IH, m) , 8.65 (IH, d) .
Compound 22
1H-NMR(CDCl3) δ: 4.90(2H,t), 6.02(lH,tt), 7.36(lH,s), 8.14(1H, s), 8.70(lH,s), 9.21(lH,s) .
Compound 23
1H-NMR(CDCl3) δ: 4.87-4.90 (2H,m) , 5.99 (IH, tt) , 6.80(lH,s),
7.23(lH,s), 7.62(lH,s), 8.44(lH,s), 8.69(lH,s) .
Compound 24 1H-NMR(CDCl3) δ: 1.27(9H,s), 5.30(2H,s), 6.81(lH,d), 7.20-
7.21(lH,m), 7.59-7.60(lH,m) , 8.42(lH,s), 8.55(lH,d).
Compound 25
1H-NMR(CDCl3) δ: 4.94-5.01 (2H,m) , 7.38(lH,d), 8.14(lH,s),
8.69(lH,d) , 9.20 (IH, s) . Compound 26
1H-NMR(CDCl3) δ: 4.92-4.99 (2H,m) , 6.81(lH,d), 7.22-
7.23(lH,m), 7.61-7.62 (IH, m) , 8.44-8.45 (IH, m) , 8.69(lH,d).
Compound 29
1H-NMR(CDCl3) δ: 1.17(9H,s), 5.03(lH,d), 7.39(lH,d), 8.13(1H, s), 8.55(lH,s), 9.18(lH,s), 9.73(lH,d) .
Compound 30
1H-NMR(CDCl3) δ: 1.28(9H,s), 5.31(2H,s), 7.36(lH,d),
8.12(1H, s), 8.54(lH,d), 9.17(lH,s) .
Compound 31 1H-NMR(CDCl3) δ: 4.11(2H,q), 7.80(lH,d), 8.14(lH,s),
8.85 (IH, d) , 9.21 (IH, s) .
Compound 32
1H-NMR(CDCl3) δ: 4.12(2H,q), 7.22(lH,s), 7.24(lH,d), 7.62- 7.63(lH,m), 8.44(lH,s), 8.84(lH,s).
Compound 33
1H-NMR(CDCl3) δ: 1.88(6H,d), 6.72(lH,d), 7.20-7.21 (IH, m) ,
7.59-7.60(lH,m) , 8.41-8.42 (IH, m) , 8.63(lH,d) .
Compound 34 1H-NMR(CDCl3) δ: 4.96(2H,t), 6.03(lH,tt), 8.24(lH,s),
8.51(lH,s), 9.12(lH,s).
Compound 35
1H-NMR(CDCl3) δ: 4.90-4.97 (2H,m) , 6.03 (IH, tt) , 7.24-
7.25(lH,m), 7.82-7.83 (IH, m) , 8.45(lH,s), 8.49(lH,d). Compound 36
1H-NMR(CDCl3) δ: 3.45(3H,s), 3.76-3.78 (2H,m) , 4.60-
4.63(2H,m), 7.29(lH,d), 8. H(IH, s), 8.64(lH,d), 9.18(lH,s) .
Compound 37
1H-NMR(CDCl3) δ: 3.45(3H,s), 3.75-3.77 (2H,m) , 4.60- 4.62(2H,m), 6.73(lH,s), 7.20-7.21 (IH, m) , 7.58-7.59 (IH, m) ,
8.40(lH,s), 8.64(lH,s).
Compound 38
1H-NMR(CDCl3) δ: 1.56(3H,d), 5.86-5.92 (lH,m) , 7.33(lH,d),
8.13(1H, s), 8.67(lH,d), 9.19(lH,s) . Compound 39
1H-NMR(CDCl3) δ: 1.55(3H,d), 5.84-5.91 (IH, m) , 6.76(lH,s),
7.22(lH,s), 7.61(lH,s), 8.44(lH,s), 8.66(lH,d) .
Compound 40
1H-NMR(CDCl3) δ: : 6.55-6.61 (IH, m) , 7.51(lH,d), 8.16(lH,s), 8.74(lH,d), 9.22(lH,s).
Compound 41
1H-NMR(CDCl3) δ: 6.55-6.61 (IH, m) , 6.95(lH,d), 7.24(lH,s),
7.64-7.65 (IH, m) , 8.48(lH,s), 8.73(lH,d) . Compound 42
1H-NMR(CDCl3) δ: 4.70-4.71 (2H,m) , 4.82-4.83 (2H,m) , 5.72-
5.78(lH,m), 7.33(lH,d), 8.12(lH,s), 8.65(lH,d), 9.18(lH,s) .
Compound 43
1H-NMR(CDCl3) δ: 4.70-4.71 (2H,m) , 4.82-4.83 (2H,m) , 5.71- 5.76(lH,m) , 6.77(lH,d), 7.21-7.22 (IH, m) , 7.60-7.61 (IH, m) ,
8.42-8.43(lH,m) , 8.65(lH,d) .
Compound 44
1H-NMR(CDCl3) δ: 4.84-4.89 (2H,m) , 5.06-5.17 (IH, m) ,
7.36(lH,s), 8.14(1H, s), 8.70(lH,s), 9.20(lH,s). Compound 45
1H-NMR(CDCl3) δ: 4.85-4.89 (2H,m) , 5.02-5.19 (IH, m) ,
6.80(lH,d), 7.22-7.23(lH,m) , 7.61-7.62 (IH, m) , 8.44-
8.45(lH,m), 8.69(lH,d).
Compound 46 1H-NMR(CDCl3) δ: 1.58(3H,d), 5.96-6.04 (IH, m) , 7.31(lH,d),
8.13(1H, s), 8.67(lH,d), 9.19(lH,s) .
Compound 47
1H-NMR(CDCl3) δ: 1.57(3H,d), 5.96-6.04 (IH, m) , 6.75(lH,d),
7.22(lH,s), 7.61-7.62 (IH, m) , 8.44(lH,s), 8.67(lH,s). Compound 48
1H-NMR(CDCl3) δ: 2.64-2.70 (2H,m) , 4.69(2H,t), 7.26(lH,d),
8.12(1H, s), 8.66(lH,d), 9.19(lH,s) .
Compound 49
1H-NMR(CDCl3) δ: 2.63-2.68 (2H,m) , 4.68(2H,t), 6.69(lH,d), 7.21-7.22(lH,m), 7.60-7.61 (IH, m) , 8.42-8.43 (IH, m) ,
8.66(lH,d) .
Compound 51
1H-NMR(CDCl3) δ: 0.15(9H,t), 4.13(2H,s), 7.23(lH,d), 8. H(IH, s), 8.65(lH,d), 9.18(lH,s) .
Compound 52
1H-NMR(CDCl3) δ: 0.15(9H,s), 4.13(2H,s), 6.67(lH,s),
7.21(lH,s), 7.61(lH,s), 8.42(lH,s), 8.65(lH,s) .
Compound 53 1H-NMR(CDCl3) δ: 0.10(9H,s), 1.15-1.19 (2H,m) , 4.52-
4.56(2H,m), 7.17(lH,d), 8. H(IH, s), 8.64(lH,d), 9.18(lH,s) .
Compound 54
1H-NMR(CDCl3) δ: 0.10(9H,s), 1.14-1.18 (2H,m) , 4.51-
4.55(2H,m), 6.61(lH,d), 7.20-7.21 (IH, m) , 7.59-7.60 (IH, m) , 8.40-8.41(lH,m) , 8.64(lH,d) .
Compound 55
1H-NMR(CDCl3) δ: 5.03(2H,t), 6.08 (IH, tt) , 7.38(lH,d),
8.14(1H, s), 8.69(lH,d), 9.20(lH,s) .
Compound 56 1H-NMR(CDCl3) δ: 5.01(2H,t), 6.08 (IH, tt) f 6.81(lH,d), 7.22-
7.23(lH,m), 7.62-7.63 (IH, m) , 8.44-8.45 (IH, m) , 8.69(lH,d) .
Compound 57
1H-NMR(CDCl3) δ: 4.85-4.94 (2H,m) , 5.98(lH,tt), 7.32(lH,d),
8.69(lH,d), 9.07(1H, s). Compound 58
1H-NMR(CDCl3) δ: 4.87-4.95 (2H,m) , 5.99(lH,tt), 7.43(lH,d),
8.74 (IH, d) , 9.27 (IH, s) .
Compound 59
1H-NMR(CDCl3) δ: 4.06(3H,s), 4.85-4.95 (2H,m) , 5.98(lH,tt), 7.51-7.53 (IH, m) , 8.72-8.74 (IH, m) , 9.27(lH,s) .
Compound 60
1H-NMR(CDCl3) δ: 4.85-4.94 (2H,m) , 5.98 (IH, tt) , 7.30(lH,d),
8.69(lH,d), 9.10(lH,s). Compound 61
1H-NMR(CDCl3) δ: 2.50(3H,s), 4.82-4.92 (2H,m) , 5.85-
6.12(lH,m), 7.28(lH,d), 8.65(lH,d), 9.06(lH,s) .
Compound 62
1H-NMR(CDCl3) δ: 2.94(3H,s), 4.84-4.92 (2H,m) , 6.00(lH,tt), 7.43(lH,d), 7.93(lH,s), 8.72(lH,d) .
Compound 63
1H-NMR(CDCl3) δ: 4.87-4.95 (2H,m) , 5.84-6.13 (IH, m) ,
7.53(lH,s), 8.74(lH,s), 9.31(lH,s) .
Compound 64 1H-NMR(DMSO-D6) δ: 5.08(2H,t), 6.60-6.86 (IH, m) , 7.43(lH,d),
7.85(lH,brs) , 8.12 (IH, brs) , 8.92(lH,d), 9.56(lH,s).
Compound 65
1H-NMR(CDCl3) δ: 4.83(2H,d), 6.06(lH,t), 6.77(lH,d),
7.22(lH,s), 7.61(lH,d), 8.43(lH,s), 8.66(lH,s) . Compound 66
1H-NMR(CDCl3) δ: 4.84(2H,d), 6.07(lH,t), 7.33(lH,d),
8.13(lH,s), 8.67(lH,d), 9.19(lH,s) .
Compound 67
1H-NMR(CDCl3) δ: 5.25-5.33 (2H, m) , 7.33(lH,d), 8.13(lH,s), 8.67(lH,d), 9.19(lH,s) .
Compound 68
1H-NMR(CDCl3) δ: 2.35-2.43 (2H,m) , 4.36(2H,t), 4.41(2H,t),
6.78(lH,s), 7.97(lH,s), 8.08(lH,s), 8.56(lH,s) .
Compound 69 1H-NMR(CDCl3) δ: 2.34(6H,s), 2.75(2H,t), 4.55(2H,t),
7.27(lH,d), 8. H(IH, s), 8.64(lH,d), 9.18(lH,s) .
Compound 70
1H-NMR(CDCl3) δ: 2.34(6H,s), 2.73(2H,t), 4.54(2H,t), 6.72- 6.74(lH,m), 7.19-7.21(lH,m) , 7.57-7.59 (IH, m) , 8.40(lH,s),
8.64 (IH, s) .
Compound 71
1H-NMR(DMSO-D6) δ: 5.02 (2H, t) , 6.14 (2H, brs) , 6.57-6.87 (IH, m) ,
6.94(lH,s), 8.74(lH,s), 9.01(lH,s) . Compound 72
1H-NMR(DMSO-D6) δ: 5.02(2H,t), 6.56-6.88 (IH, m) , 7.13(lH,s),
7.72(lH,s), 7.79(2H,brs) , 8.80(lH,s) .
Compound 73
1H-NMR(CDCl3) δ: 5.05-5.07 (2H, m) , 5.46-5.49 (IH, m) , 5.55- 5.58(lH,m), 7.31-7.33 (IH, m) , 8.13(lH,s), 8.66(lH,s),
9.19(1H, s) .
Compound 74
1H-NMR(CDCl3) δ: 5.04-5.06 (2H,m) , 5.47-5.49 (IH, m) , 5.56-
5.58(lH,m), 6.75(lH,s), 7.21-7.23 (IH, m) , 7.60-7.62 (lH,m) , 8.43 (IH, s) , 8.66(lH,s) .
Compound 75
1H-NMR(CDCl3) δ: 5.33(2H,s), 7.32(lH,d), 8.13(lH,s),
8.67(lH,d), 9.19(1H, s) .
Compound 76 1H-NMR(CDCl3) δ: 5.32(2H,s), 6.76(lH,d), 7.22(lH,s), 7.60-
7.62(lH,m), 8.43(lH,s), 8.67(lH,d) .
Compound 77
1H-NMR(CDCl3) δ: 4.84-4.97 (2H,m) , 5.07-5.24 (IH, m) ,
8.22(lH,s), 8.63(lH,s), 9.09(lH,s) . Compound 78
1H-NMR(CDCl3) δ: 4.92-4.96 (2H,m) , 6.06 (IH, tt) , 8.22(lH,s),
8.63 (IH, s) , 9.09(1H, s) .
Compound 79 1H-NMR(CDCl3) δ: 5.22(2H,s), 8.22(lH,s), 8.63(lH,s),
9.09(1H, s) .
Compound 80
1H-NMR(CDCl3) δ: 5.15(2H,s), 6.74 (2H, brs) , 7.37(lH,d),
7.60 (IH, s) , 8.64 (IH, d) . Compound 81
1H-NMR(CDCl3) δ: 2.93(2H,t), 4.64(2H,t), 5.54-5.56 (IH, m) ,
5.72-5.74 (IH, m) , 7.22-7.24 (IH, m) , 8.12(lH,s), 8.66(lH,s),
9.18 (IH, s) .
Compound 82 1H-NMR(CDCl3) δ: 2.92(2H,t), 4.64(2H,t), 5.56(lH,d),
5.73(lH,d), 6.67(lH,d), 7.21(lH,s), 7.59-7.61 (lH,m) ,
8.41 (IH, s) , 8.66(lH,d) .
Compound 83
1H-NMR(CDCl3) δ: 4.89-4.95 (2H,m) , 5.05-5.22 (IH, m) , 8.24(lH,s), 8.51(lH,s), 9.12(lH,s) .
Compound 84
1H-NMR(CDCl3) δ: 5.23(2H,s), 8.24(lH,s), 8.50(lH,s),
9.12 (IH, s) .
Compound 85 1H-NMR(CDCl3) δ: 2.23(3H,s), 4.86(2H,s), 7.36(lH,s),
8.13(1H, s), 8.67(lH,s), 9.19(lH,s).
Compound 86
1H-NMR(CDCl3) δ: 2.23(3H,s), 4.85(2H,s), 6.81(lH,d), 7.21-
7.24 (IH, m), 7.61-7.64 (IH, m) , 8.43-8.45 (IH, m) , 8.67(lH,d) . Compound 87
1H-NMR(CDCl3) δ: 4.78-4.91 (2H,m) , 4.99-5.21 (IH, m) ,
6.66(2H,brs) , 7.29(lH,d), 7.60(lH,s), 8.65(lH,d).
Compound 88 1H-NMR(DMSO-D6) δ: 1.50(3H,d), 5.80-5.94 (IH, m) f 6.62-
6.93(lH,m), 7.32(lH,d), 8.42(lH,s), 8.89(lH,d), 9.49(lH,s) .
Compound 89
1H-NMR(CDCl3) δ: 4.88-5.15 (3H,m) , 5.53 (2H,brs) , 8.09(lH,s),
8.17 (IH, s) , 9.23(lH,s) . Compound 90
1H-NMR(CDCl3) δ: 4.91-5.07 (3H,m) , 8.17(lH,s), 8.76(lH,s),
9.22(lH,s) .
Compound 91
1H-NMR(CDCl3) δ: 2.54(3H,d), 4.84-4.91 (2H,m) , 4.99- 5.16(lH,m), 8.15(lH,s), 8.56(lH,d), 9. H(IH, s) .
Compound 92
1H-NMR(CDCl3) δ: 2.53(3H,s), 4.87-4.90 (2H,m) , 6.00 ( IH, tt) ,
8.15(1H, s), 8.56(lH,s), 9.10(lH,s).
Compound 93 1H-NMR(CDCl3) δ: 2.60(3H,d), 5.15(2H,s), 8.15(lH,s),
8.55 (lH,d) , 9. H(IH, s) .
Compound 94
1H-NMR(CDCl3) δ: 1.70(6H,s), 4.53(2H,s), 7.31(lH,d),
8.13(lH,s), 8.65(lH,d), 9.19(lH,s). Compound 95
1H-NMR(CDCl3) δ: 1.20(6H,d), 3.64-3.71 (IH, m) f 3.79-
3.81(2H,m), 4.57-4.60 (2H,m) , 7.27(lH,d), 8. H(IH, s) ,
8.64 (IH, d) , 9.18 (IH, s) .
Compound 96 1H-NMR(CDCl3 ) δ: 0.91 (6H,d) , 1.86-1.92 (IH, m) , 3.29 (2H,d) ,
3.79-3.81 (2H,m) , 4.59-4.62 (2H,m) , 7.27 (lH,d) , 8.12 (lH, s) ,
8.64 (IH, d) , 9.18 (IH, s) .
Compound 97 1H-NMR(CDCl3) δ: 1.18(9H,s), 1.38(3H,d), 3.47-3.50 (2H,m) ,
5.43-5.45(lH,m), 7.20(lH,d), 8. H(IH, s), 8.63(lH,d),
9.17 (IH, s) .
Compound 98
1H-NMR(CDCl3) δ: 4.80-4.91 (2H,m) , 5.00-5.20 (IH, m) f 6.39(2H,brs) , 6.67(lH,s), 6.75(lH,d), 6.88(lH,d), 8.66(lH,s)
Compound 99
1H-NMR(CDCl3) δ: 4.87 (2H, tt) , 5.98(lH,tt), 6.28 (2H,brs) ,
6.67(lH,d), 6.75(lH,d), 6.89(lH,d), 8.65(lH,d) .
Compound 100 1H-NMR(CDCl3) δ: 4.81-4.94 (2H,m) , 4.99-5.20 (IH, m) ,
7.36(lH,d), 8.02(1H, s), 8.81(lH,d) .
Compound 101
1H-NMR(CDCl3) δ: 4.83-4.94 (2H,m) , 5.00-5.20 (IH, m) ,
7.37(lH,s), 8.06(1H, s), 8.81(lH,s) . Compound 102
1H-NMR(CDCl3) δ: 4.82-4.99 (2H,m) , 5.09-5.26 (IH, m) ,
8.21(lH,s), 8.64(lH,s), 9.06(lH,s) .
Compound 103
1H-NMR(CDCl3) δ: 4.90-4.96 (2H,m) , 6.08(lH,tt), 8.21(lH,s), 8.64 (IH, s) , 9.05 (IH, s) .
Compound 104
1H-NMR(CDCl3) δ: 5.21(2H,s), 8.22(lH,s), 8.63(lH,s),
9.05(1H, s) .
Compound 105 1H-NMR(CDCl3 ) δ: 1.22 (9H,s) , 3.72 (2H,t) , 4.52 (2H,t) ,
6.66 (2H,brs) , 7.19 (lH,d) , 7.58 (lH, s) , 8.59 (lH,d) .
Compound 106
1H-NMR(CDCl3) δ: 2.66(3H,s), 4.77-4.88 (2H,m) , 5.00- 5.21(lH,m), 7.16(lH,s), 8. H(IH, s), 9.19(lH,s).
Compound 107
1H-NMR(CDCl3) δ: 2.66(3H,s), 4.84-4.88 (2H,m) , 6.00(lH,tt),
7.15(1H, s), 8. H(IH, s), 9.19(lH,s) .
Compound 108 1H-NMR(CDCl3) δ: 2.66(3H,s), 5.14(2H,s), 7.23(lH,s),
8.12 (IH, s) , 9.20 (IH, s) .
Compound 109
1H-NMR(CDCl3) δ: 1.54-1.59 (3H,m) , 4.94-5.22 (IH, m) , 5.75-
5.89(lH,m), 7.31(lH,d), 8.13(lH,s), 8.68(lH,d), 9.19(lH,s) . Compound 110
1H-NMR(CDCl3) δ: 1.56(3H,t), 4.93-5.21 (IH, m) , 5.76-
5.89(lH,m), 6.73-6.76 (IH, m) , 7.22-7.24 (IH, m) , 7.60-
7.62(lH,m), 8.44(lH,s), 8.67-8.69 (IH, m) .
Compound 111 1H-NMR(CDCl3) δ: 2.25(3H,s), 5.05(2H,s), 7.37(lH,s),
8.13(1H, s), 8.59(lH,s), 9.18(lH,s) .
Compound 112
1H-NMR(CDCl3) δ: 0.96(9H,s), 3.21(2H,d), 4.83-5.16 (3H,m) ,
6.96(lH,s), 8.08(1H, s), 8.17(lH,s), 9.23(lH,s). Compound 113
1H-NMR(CDCl3) δ: 5.00(2H,t), 7.39(lH,s), 8.14(lH,s),
8.68(lH,s), 9.20(lH,s) .
Compound 114
1H-NMR(CDCl3) δ: 5.04(2H,t), 7.39(lH,s), 8.13(lH,s), 8.68 (IH, s) , 9.20 (IH, s) .
Compound 115
1H-NMR(CDCl3 ) δ: 1.70-1.78 (2H,m) , 1.82-1.91 (3H,m) ,
3.25 (2H,t) , 3.71-3.77 (2H,m) , 6.73 (2H, brs) , 7.58 (lH, s) , 7.66 (lH,d) , 8.72 (lH,d) .
Compound 116
1H-NMR(CDCl3 ) δ: 1.25 (3H,t) , 3.06 (2H,q) , 4.84-4.92 (2H,m) ,
5.01-5.12 (IH, m) , 8.15 (lH, s) , 8.56 (lH, s) , 9.12 (lH,s) .
Compound 117 1H-NMR(CDCl3 ) δ: 1.24 (3H,t) , 3.05 (2H,q) , 4.88-4.91 (2H,m) ,
5.99 (lH,tt) , 8.14 (1H, s) , 8.56 (lH, s) , 9. H (IH, s) .
Compound 118
1H-NMR(CDCl3) δ: 1.31(3H,t), 3.11(2H,q), 5.16(2H,s),
8.15 (lH, s) , 8.55 (lH, s) , 9. H (IH, s) . Compound 119
1H-NMR(CDCl3 ) δ: 4.83-4.97 (2H,m) , 6.05 (lH,t) , 7.33 (lH, s) ,
8.13 (lH, s) , 8.66 (lH, s) , 9.19 (lH, s) .
Compound 120
1H-NMR(CDCl3 ) δ: 1.60 (3H, s) , 4.81 (2H, s) , 8.21 (lH, s) , 8.61 (lH, s) , 9.07 (IH, s) .
Compound 121
1H-NMR(CDCl3 ) δ: 5.08 (2H,t) , 6.10 (IH, tt) , 8.22 (lH, s) ,
8.63 (lH, s) , 9.09 (lH, s) .
Compound 122 1H-NMR(CDCl3 ) δ: 1.62 (3H,d) , 5.77-6.20 (2H,m) , 8.21 (lH, s) ,
8.61 (IH, s) , 9.07 (IH, s) .
Compound 123
1H-NMR(CDCl3 ) δ: 1.61-1.66 (3H,m) , 4.98-5.30 (IH, m) , 5.70-
5.86 (lH,m) , 8.22 (lH, s) , 8.61-8.62 (IH, m) , 9.08 (lH, s) . Compound 124
1H-NMR(CDCl3) δ: 1.35(6H,d), 3.78-3.85 (IH, m) , 4.88-
5.16(3H,m), 8.14(lH,s), 8.56(lH,s), 8.91(lH,s) .
Compound 125 1H-NMR(CDCl3) δ: 1.35(6H,d), 3.74-3.81 (IH, m) , 4.89-
4.92(2H,m), 6.00 (IH, tt) , 8.13{lH,s), 8.56(lH,s), 8.89(lH,s).
Compound 126
1H-NMR(CDCl3) δ: 0.17(9H,s), 4.25(2H,s), 8.20(lH,s),
8.58 (IH, s) , 9.02 (IH, s) . Compound 127
1H-NMR(CDCl3) δ: 0.12(9H,s), 1.22-1.28 (2H,m) , 4.62-
4.69(2H,m), 8.20(lH,s), 8.58(lH,s), 9.02(lH,s) .
Compound 128
1H-NMR(CDCl3) δ: 1.23(9H,s), 3.79(2H,t), 4.64(2H,t), 8.20(lH,s), 8.58(lH,s), 9.03(lH,s).
Compound 129
1H-NMR(CDCl3) δ: 1.25(9H,s), 4.88-5.14 (3H,m) , 8. H(IH, s),
8.52(lH,s), 8.53(lH,s).
Compound 130 1H-NMR(CDCl3) δ: 1.24(9H,s), 4.89-4.93 (2H,m) , 5.99(lH,tt),
8. H(IH, s), 8.51(lH,s), 8.53(lH,s) .
Compound 131
1H-NMR(CDCl3) δ: 1.57(3H,s), 2.51(3H,d), 4.90-5.18 (IH, m) ,
5.77-5.89(lH,m) , 8.15(lH,s), 8.55(lH,d), 9.10(lH,d). Compound 132
1H-NMR(CDCl3) δ: 1.56(3H,s), 2.49-2.51 (3H,m) , 5.80-
6.12(2H,m), 8.14(lH,s), 8.55(lH,s), 9.09(lH,s) .
Compound 133
1H-NMR(CDCl3) δ: 2.54(3H,s), 5.01(2H,t), 6.09(lH,tt), 8.15(1H, s) , 8.56(lH,s) , 9. H(IH, s) .
Compound 134
1H-NMR(CDCl3) δ: 1.55(3H,s), 2.50(3H,s), 4.74(2H,s),
8.14(lH,s), 8.55(lH,s), 9.09(lH,s) . Compound 135
1H-NMR(CDCl3) δ: 1.24(9H,s), 2.47(3H,s), 3.76(2H,t),
4.56(2H,t), 8.13(1H, s), 8.52(lH,s), 9.04(lH,s).
Compound 136
1H-NMR(CDCl3) δ: 0.16(9H,s), 2.45(3H,s), 4.15(2H,s), 8.13(1H, s), 8.53(lH,s), 9.03(lH,s).
Compound 137
1H-NMR(CDCl3) δ: 0.10(9H,s), 1.15-1.23 (2H,m) , 2.45(3H,s),
4.52-4.58 (2H,m) , 8.13(lH,s), 8.52(lH,s), 9.03(lH,s) .
Compound 138 1H-NMR(CDCl3) δ: 1.79(3H,d), 6.10(lH,q), 8.22(lH,s),
8.62 (IH, s) , 9.08 (IH, s) .
Compound 139
1H-NMR(CDCl3) δ: 2.29(3H,s), 4.92(2H,s), 8.22(lH,s),
8.61(lH,s) , 9.08 (IH, s) . Compound 140
1H-NMR(CDCl3) δ: 1.75(3H,d), 2.54(3H,s), 6.06(lH,q),
8.15(lH,s), 8.55(lH,s), 9.09(lH,s) .
Compound 141
1H-NMR(CDCl3) δ: 2.25(3H,s), 2.56(3H,s), 4.84(2H,s), 8.15(1H, s), 8.54(lH,s), 9.09(lH,s) .
Compound 142
1H-NMR(CDCl3) δ: 2.66-2.82 (2H,m) , 4.86(2H,t), 8.21(lH,s),
8.62 (IH, s) , 9.06(lH,s) .
Compound 143 1H-NMR(CDCl3) δ: 2.48(3H,s), 2.62-2.77 (2H,m) , 4.79(2H,t),
8.14(lH,s), 8.55(lH,s), 9.07(lH,s) .
Compound 144
1H-NMR(CDCl3) δ: 2.60-2.75 (2H, m) , 4.78 (2H, t) , 7.26(lH,s), 8.12(lH,s), 8.67(lH,s), 9.19(lH,s) .
Compound 145(PC-5067)
1H-NMR(CDCl3) δ: 5.08(2H,t), 8.22(lH,s), 8.63(lH,s),
9.09(1H, s) .
Compound 146 1H-NMR(CDCl3) δ: 2.54(3H,s), 5.00(2H,t), 8.15(lH,s),
8.56(lH,s), 9. H(IH, s).
Compound 147
1H-NMR(CDCl3) δ: 5.02(2H,t), 7.38(lH,s), 8.14(lH,s),
8.69(lH,s) , 9.20 (IH, s) . Compound 148
1H-NMR(CDCl3) δ: 2.12-2.21 (2H,m) , 2.28-2.42 (2H,m) ,
4.61(2H,t), 8.21(lH,s), 8.59(lH,s), 9.05(lH,s) .
Compound 149
1H-NMR(CDCl3) δ: 2.08-2.18 (2H,m) , 2.25-2.38 (2H,m) , 2.48(3H,s), 4.53(2H,t), 8.14(lH,s), 8.53(lH,s), 9.06(lH,s) .
Compound 150
1H-NMR(CDCl3) δ: 2.05-2.14 (2H,m) , 2.23-2.37 (2H,m) ,
4.51(2H,t), 7.23(lH,s), 8.12(lH,s), 8.65(lH,s), 9.18(lH,s) .
Compound 151 1H-NMR(DMSO-D6) δ: 3.94(2H,t), 5.11(2H,t), 6.03 (lH,brs) ,
7.35(lH,s), 8.42(lH,s), 8.89(lH,s), 9.49(lH,s) .
Compound 152
1H-NMR(CDCl3) δ: 3.99(3H,s), 4.91-4.98 (2H,m) , 5.04-
5.15(lH,m), 8.20(lH,s), 8.50(lH,s), 9.09(lH,s) . Compound 153
1H-NMR(CDCl3) δ: 4.00(3H,s), 4.92-4.99 (2H,m) , 6.01 (IH, tt) ,
8.20(lH,s), 8.50(lH,s), 9.09(lH,s) .
Compound 154 1H-NMR(CDCl3) δ: 3.51(3H,s), 3.88(2H,t), 4.98(2H,t),
7.37(lH,s), 8.13(lH,s), 8.68(lH,s), 9.19(lH,s) .
Compound 155
1H-NMR(CDCl3) δ: 1.74(6H,s), 4.59(2H,s), 8.21(lH,s),
8.59(lH,s) , 9.06(lH,s) . Compound 156
1H-NMR(CDCl3) δ: 1.72(6H,s), 2.54(3H,s), 4.52(2H,s),
8.14(lH,s), 8.53(lH,s), 9.07(lH,s) .
Compound 157
1H-NMR(CDCl3) δ: 5.03(2H,t), 7.38(lH,d), 8.14(lH,s), 8.69(lH,d), 9.20(lH,s).
Compound 158
1H-NMR(CDCl3) δ: 5.03(2H,t), 7.38(lH,s), 8.14(lH,s),
8.69(lH,s) , 9.20 (IH, s) .
Compound 159 1H-NMR(CDCl3) δ: 5.03(2H,t), 7.38(lH,d), 8.14(lH,s),
8.69(lH,d) , 9.20 (IH, s) .
Compound 160
1H-NMR(CDCl3) δ: 5.03(2H,t), 7.38(lH,d), 8.14(lH,s),
8.69(lH,d), 9.20(lH,s) . Compound 161
1H-NMR(CDCl3) δ: 4.47-4.58 (IH, m) , 4.71-4.87 (2H,m) , 7.17-
7.19(2H,m), 7.43-7.45 (3H,m) , 7.90(lH,s), 8.61(lH,s),
8.77 (IH, s) .
Compound 162 1H-NMR(CDCl3 ) δ: 4.82-4.85 (2H,m) , 5.60 (IH, tt) , 7.16-
7.20 (2H,m) , 7.41-7.44 (3H,m) , 7.90 (lH,s) , 8.54 (lH,s) ,
8.77 (lH, s) .
Compound 163 1H-NMR(CDCl3 ) δ: 4.45-4.64 ( IH, m) , 4.70-4.92 (2H,m) , 7.17-
7.20 (lH,m) , 7.34-7.35 (IH, m) , 7.40-7.42 (lH,m) , 7.49-
7.51 (lH,m) , 7.84 (lH,s) , 8.78 (lH,s) , 8.99 (lH,s) .
Compound 164
1H-NMR(CDCl3 ) δ: 4.78-4.87 (2H,m) , 5.59 (IH, tt) , 7.18- 7.20 (lH,m) , 7.34 (lH,td) , 7.40 (lH,td) , 7.47-7.49 (IH, m) ,
7.83 (lH,s) , 8.78 (lH,s) , 8.95 (lH,s) .
Compound 165
1H-NMR(CDCl3 ) δ: 4.91-5.05 (2H,m) , 5.14-5.25 (IH, m) ,
8.29(lH,s) , 8.82 (lH,s) , 9.27 (lH,s) . Compound 166
1H-NMR(CDCl3 ) δ: 4.99-5.02 (2H,m) , 6.09 (IH, tt) , 8.28 (lH, s) ,
8.81 (IH, s) , 9.26 (lH,s) .
Compound 167
1H-NMR(CDCl3 ) δ: 2.33 (3H,d) , 4.85-4.92 (2H,m) , 5.01- 5.12 (lH,m) , 7.22-7.23 (IH, m) , 7.47-7.48 (lH,m) , 8.07-
8.08 (IH, m) , 8.60 (IH, d) .
Compound 168
1H-NMR(CDCl3 ) δ: 2.33 (3H,d) , 4.86-4.93 (2H,m) , 5.99(lH,tt) ,
7.22-7.23 (lH,m) , 7.46-7.47 (IH, m) , 8.07-8.08 (IH, m) , 8.60 (lH,d) .
Compound 169
1H-NMR(CDCl3 ) δ: 4.82-4.99 (2H,m) , 5.03-5.26 (IH, m) ,
7.22 (lH,s) , 7.87-7.88 (IH, m) , 8.53 (lH,s) , 8.59(lH,s) .
Compound 170 1H-NMR(CDCl3 ) δ: 4.91-4.94 (2H,m) , 6.05 (IH, tt) f 7.21-
7.22 (lH,m) , 7.86-7.87 (IH, m) , 8.52-8.53 ( IH, m) , 8.59 (lH, s) .
Compound 171
1H-NMR(CDCl3) δ: 2.53-2.68 (2H,m) , 3.45-3.51 (2H,m) , 7.73(lH,d), 8.13(1H, s), 8.83(lH,d), 9.20(lH,s) .
Compound 172
1H-NMR(CDCl3) δ: 2.53-2.68 (2H,m) , 3.46-3.52 (2H,m) ,
8.21(lH,s), 8.80(lH,s), 9.08(lH,s) .
Compound 173 1H-NMR(CDCl3) δ: 2.53-2.68 ( 5H,m) , 3.46-3.52 (2H,m) ,
8.14(1H, s), 8.74(lH,s), 9.08(lH,s) .
Compound 174
1H-NMR(CDCl3) δ: 1.91(6H,s), 4.66(2H,s), 8.21(lH,s), 8.58-
8.60 (IH, m) , 9.05(lH,s) . Compound 175
1H-NMR(CDCl3) δ: 1.82(3H,t), 4.70(2H,t), 8.21(lH,s),
8.61(lH,s), 9.07(lH,s).
Compound 176
1H-NMR(CDCl3) δ: 5.06(2H,t), 6.14(lH,tt), 8.22(lH,s), 8.63 (IH, s) , 9.09(lH,s) .
Compound 177
1H-NMR(CDCl3) δ: 1.76(3H,t), 4.64(2H,t), 7.33-7.35 (IH, m) ,
8.13(1H, s), 8.67(lH,s), 9.19(lH,s) .
Compound 178 1H-NMR(CDCl3) δ: 5.00(2H,t), 6.09(lH,tt), 7.38(lH,s),
8.14(1H, s), 8.69(lH,s), 9.20(lH,s) .
Compound 179
1H-NMR(CDCl3) δ: 1.78(3H,t), 2.53(3H,s), 4.63(2H,t),
8.14(1H, s), 8.54(lH,s), 9.09(lH,s) . Compound 180
1H-NMR(CDCl3 ) δ: 2.54 (3H,s) , 4.99(2H,t) , 6.09 (IH, tt) ,
8.15 (1H, s) , 8.56(lH,s) , 9.10 (lH,s) .
Compound 181 1H-NMR(CDCl3 ) δ: 1.55 (1.5H, d) , 1.58 (1.5H,d) , 4.26-
4.62 (1.0H,m) , 5.49-5.60 (0.5H,m) , 5.61-5.71 (0.5H,m) , 7.15-
7.16(2. OH, m) , 7.42-7.44 (3. OH, m) , 7.88-7.89 (1. OH, m) , 8.59-
8.61 (1.0H,m) , 8.75-8.76 (1. OH, m) .
Compound 182 1H-NMR(CDCl3 ) δ: 1.29 (3H,s) , 4.70 (2H,s) , 7.14-7.16 (2H,m) ,
7.39-7.41 (3H,m) , 7.91 (lH,s) , 8.49 (lH,s) , 8.76 (lH,s) .
Compound 183
1H-NMR(CDCl3 ) δ: 5.16(2H,s) , 7.24-7.27 (2H,m) , 7.41-
7.41 (3H,m) , 7.93 (lH,s) , 8.48 (lH,s) , 8.77 (lH,s) . Compound 184
1H-NMR(CDCl3 ) δ: 1.98-2.08 ( 4H,m) , 4.49 (2H,t) , 7.16-
7.16(2H,m) , 7.40-7.41 (3H,m) , 7.90 (lH,s) , 8.43 (lH, s) ,
8.74 (IH, s) .
Compound 185 1H-NMR(CDCl3) δ: 0.87-0.97 (3H,m) , 1.30-1.41 (2H,m) , 1.43-
1.54(2H,m), 2.28-2.40 (2H,m) , 5.08-5.17 (2H,m) , 7.25(lH,s),
8.13(lH,s), 8.65-8.68 (IH, m) , 9.19(lH,s) .
Compound 186
1H-NMR(CDCl3) δ: 0.86-0.97 (3H,m) , 1.24-1.89 ( 6H,m) , 2.28- 2.44(lH,m), 4.38-5.02 (3H,m) , 7.26(lH,s), 8.13(lH,s), 8.64-
8.68(lH,m), 9.17-9.20 (IH, m) .
Compound 187
1H-NMR(CDCl3) δ: 3.97-4.14 (4H,m) , 4.85-5.03 (2H,m) ,
5.93(lH,tt), 7.37(lH,s), 8.13(lH,s), 8.68(lH,s), 9.20(lH,s) . Compound 188
1H-NMR(CDCl3 ) δ: 4.80-4.97 (2H,m) , 5.06-5.27 (IH, m) ,
6.29 (2H,brs) , 7.67 (lH,s) , 8.55 (lH,s) .
Compound 189 1H-NMR(CDCl3 ) δ: 2.54 (3H,s) , 4.80-4.90 (2H,m) , 4.96-
5.18 (lH,m) , 6.33 (2H,brs) , 7.60 (lH,s) , 8.52 (lH,s) .
Compound 190
1H-NMR(CDCl3 ) δ: 4.73-4.76 (2H,m) , 5.00-5.18 (3H,m) ,
6.71 (lH,s) , 8.08 (1H, s) , 9.07 (lH,s) . Compound 191
1H-NMR(CDCl3 ) δ: 4.08-4.17 (2H,m) , 4.90-5.10 (IH, m) ,
7.81 (lH,d) , 8.14 (1H, s) , 8.84 (lH,d) , 9.21 (lH,s) .
Compound 192
1H-NMR(CDCl3 ) δ: 3.64-3.77 (IH, m) , 3.92-4.10 (IH, m) , 5.16- 5.33 (lH,m) , 8.21-8.21 (IH, m) , 8.60-8.62 (lH,m) , 9. H (IH, s) ,
9.30 (lH,s) .
Compound 193
1H-NMR(CDCl3) δ: 4.26-4.39 (IH, m) , 4.46-4.53 (lH,m) , 5.21-
5.37 (lH,m) , 8.24 (lH, s) , 8.54 (lH,d) , 9.25 (lH,d) , 9.32 (lH, s) . Compound 194
1H-NMR(CDCl3 ) δ: 2.23 (3H, s) , 4.82-4.85 (lH,m) , 4.97-
5.07 (lH,m) , 5.39-5.54 (IH, m) , 8.21 (lH, s) , 8.53 (lH, s) ,
9.06 (1H, s) , 9.20 (IH, s) .
Compound 195 1H-NMR(CDCl3) δ: 0.16 (9H, s) , 2.25 (3H, s) , 4.14 (2H, s) , 7.21-
7.21 (lH,m) , 7.43-7.43 (lH,m) , 8.03-8.03 (IH, m) , 8.57 (lH, s) .
Compound 196
1H-NMR(CDCl3) δ: 0.11 (9H, s) , 1.17-1.21 (2H,m) , 2.25 (3H, s) ,
4.53-4.58 (2H,m) , 7.21 (lH, s) , 7.44 (lH, s) , 8.03 (lH, s) , 8.55 (lH, s) .
Compound 1973
1H-NMR(CDCl3) δ: 2.64 (3H, s) , 4.08-4.26 (2H,m) , 4.89-5.09 (IH, m) ,
8.15 (lH, s) , 8.74 (lH, s) , 9.10 (lH, s) . Compound 198
1H-NMR(CDCl3) δ: 2.63 (3H,s) , 4.06-4.15 (2H,m) , 5.90 ( IH, tt) ,
8.15 (lH, s) , 8.74 (lH,s) , 9.09 (lH, s) .
Compound 199
1H-NMR(CDCl3) δ: 1.89-2.01 (IH, m) , 2.24 (3H, s) , 2.38-2.50 (IH, m) f 3.17-3.30 (lH,m) , 4.62-4.74 (2H,m) , 7.25 (lH, s) , 8.12 (lH, s) ,
8.67 (lH, s) , 9.19 (1H, s) .
Compound 200
1H-NMR(CDCl3) δ: 1.93-2.05 (IH, m) , 2.24(3H,s), 2.42-2.52 (4H,m) ,
3.14-3.28 (IH, m) , 4.63-4.76 (2H,m) , 8.14(lH,s), 8.54(lH,s), 9.07 (IH, s) .
Compound 201
1H-NMR(CDCl3) δ: 5.08-5.15 (2H,m) , 5.95-6.07 (IH, m) , 6.53-
6.63(lH,m) , 7.31(lH,s), 8.13(lH,s), 8.67(lH,s), 9.19(lH,s) .
Compound 202 1H-NMR(CDCl3) δ: 2.54(3H,s), 5.08-5.15 (2H,m) , 5.94-6.07 (IH, m) ,
6.55-6.67 (IH, m) , 8.15(lH,s), 8.54(lH,s), 9.09(lH,s).
Compound 203
1H-NMR(CDCl3) δ: 1.04 (3H,t) , 1.57 (lH,dt) , 1.68-1.80 (IH, m) ,
1.91-2.02 (IH, m) , 2.07-2.18 (IH, m) , 2.19-2.32 ( IH, m) , 4.53 (2H,t) , 7.22 (lH, s) , 8.12 (lH, s) , 8.65 (lH, s) , 9.18 (lH, s) .
Compound 204
1H-NMR(CDCl3) δ: 1.05 (3H,t) , 1.52-1.64 (IH, m) , 1.70-1.83 (lH,m) ,
1.93-2.04 (IH, m) , 2.10-2.33 (2H,m) , 2.47 (3H, s) , 4.55 (2H,t) ,
8.13 (1H, s) , 8.53 (lH, s) , 9.06 (lH, s) . Compound 205
1H-NMR(CDCl3) δ: 2.53(3H,s), 4.84(2H,d), 6.09(lH,t),
8.14(1H, s), 8.53(lH,s), 9.09(lH,s) .
Compound 206 1H-NMR(CDCl3) δ: 2.55(3H,s), 4.89(2H,q), 8.15(lH,s),
8.55(lH,s) , 9.10 (IH, s) .
Compound 207
1H-NMR(CDCl3) δ: 2.52(3H,s), 4.72(2H,dd), 4.84(2H,dd), 5.65-
5.82(lH,m), 8.14(lH,s), 8.53(lH,s), 9.07(lH,s) . Compound 208
1H-NMR(CDCl3) δ: 1.56-1.62 (3H,m) , 2.50(3H,s), 5.90-6.03 (IH, m) ,
8.14(1H, s), 8.54(lH,s), 9.09(lH,s) .
Compound 209
1H-NMR(CDCl3) δ: 2.23(3H,s), 2.48(3H,s), 2.93(2H,t), 4.65(2H,t), 8.13(lH,s), 8.52(lH,s), 9.05(lH,s) .
Compound 210
1H-NMR(CDCl3) δ: 1.21(6H,s), 2.38(6H,s), 2.50(3H,s),
4.38(2H,s), 8.13(1H, s), 8.53(lH,s), 9.05(lH,s) .
Compound 211 1H-NMR(CDCl3) δ: 1.19(9H,s), 1.39(3H,d), 2.44(3H,d),
3.47(lH,dd), 3.62(lH,dd), 5.39-5.49 (IH, m) , 8.13(lH,s),
8.51(lHf s) , 9.02 (IH, s) .
Compound 212
1H-NMR(CDCl3) δ: 1.39(3H,d), 2.45(3H,s), 3.41(3H,s), 3.56(lH,dd), 3.65(lH,dd), 5.53-5.62 (IH, m) , 8.13(lH,s),
8.52(lH,s), 9.03(1H, s).
Compound 213
1H-NMR(CDCl3) δ: 2.54(3H,s), 4.83-4.93 (2H,m) , 4.96-5.18 (IH, m) ,
8.55(lH,s), 9.05(1H, s) . Compound 214
1H-NMR(CDCl3) δ: 2.13(3H,s), 4.80-5.14 (3H,m) , 7.57(lH,s),
8.66(lH,s) .
Compound 215 1H-NMR(CDCl3) δ: 2.57(3H,s), 4.05(3H,s), 4.83-4.95 (2H,m) ,
4.96-5.18 (IH, m) , 8.59(lH,s), 9.16(lH,s).
Compound 216
1H-NMR(CDCl3) δ: 2.53(3H,s), 4.80-4.93 (2H,m) , 4.96-5.18 (IH, m) ,
8.55(lH,s), 9. O1(1H, s). Compound 217
1H-NMR(CDCl3) δ: 2.55(3H,s), 4.82-4.95 (2H,m) , 4.97-5.18 (IH, m) ,
8.59(lH,s), 9.19(1H, s).
Compound 218
1H-NMR(CDCl3) δ: 2.11(3H,s), 4.82-4.96 (2H,m) , 4.97-5.17 (IH, m) , 7.14 (2H,s) , 8.68 (IH, s) .
Compound 219
1H-NMR(CDCl3) δ: 1.71-1.82 (2H,m) , 1.88-1.98 (2H,m) , 2.12-
2.26(2H,m), 2.47(3H,s), 4.49(2H,t), 8.13(lH,s), 8.52(lH,s),
9.05 (IH, s) . Compound 220
1H-NMR(CDCl3) δ: 2.48(3H,s), 2.62-2.75 (2H,m) , 4.70(2H,t),
8.13(lH,s), 8.54(lH,s), 9.07(lH,s).
Compound 221
1H-NMR(CDCl3) δ: 1.69-1.82 (2H,m) , 1.86-1.96 (2H,m) , 2.12- 2.26(2H,m), 4.47(2H,t), 7.22(lH,s), 8.12(lH,s), 8.64(lH,s),
9.18 (IH, s) .
Compound 222
1H-NMR(CDCl3) δ: 2.69(3H,s), 8.16(lH,s), 8.76(lH,s),
9.16(1H, s) . Compound 223
1H-NMR(CDCl3) δ: 2.09-2.19 (5H,m) , 2.47(3H,s), 2.69(2H,t),
4.57(2H,t), 8.13(lH,s), 8.52(lH,s), 9.05(lH,s) .
Compound 224 1H-NMR(CDCl3) δ: 1.31 (3H, t) , 2.48(3H,s), 2.67(2H,q),
2.95(2H,t), 4.63(2H,t), 8.13(lH,s), 8.52(lH,s), 9.05(lH,s) .
Compound 225
1H-NMR(CDCl3) δ: 1.75-1.85 (2H,m) , 1.91-2.01 (2H,m) , 2.12(3H,s),
2.46(3H,s), 2.59(2H,t), 4.48(2H,t), 8.13(lH,s), 8.52(lH,s), 9.04(1H, s) .
Compound 226
1H-NMR(CDCl3) δ: 2.51(3H,s), 4.33-4.55 (2H,m) , 4.65-4.79 (IH, m) ,
4.94-5.10 (IH, m) , 8.12(lH,s), 8.55(lH,s), 9.08(lH,s) .
Compound 227 1H-NMR(CDCl3) δ: 2.54(3H,s), 3.70(3H,s), 3.95-4.05 (IH, m) ,
4.75-4.93 (2H,m) , 8.15(lH,s), 8.56(lH,s), 9.10(lH,s).
Compound 228
1H-NMR(CDCl3) δ: 2.54(3H,s), 2.89-3.09 (2H,m) , 4.75(2H,t),
8.15(1H, s), 8.56(lH,s), 9. H(IH, s) . Compound 229
1H-NMR(CDCl3) δ: 2.45-2.57 (3H,m) , 4.53-5.37 (4H,m) ,
8.15(lH,brs) , 8.55 (IH, brs) , 9.04-9.14 (IH, m) .
Compound 230
1H-NMR(CDCl3) δ: 1.27(3H,t), 1.68(4H,dd), 2.54(3H,s), 4.23(2H,q), 5.42(lH,q), 8.13(lH,s), 8.47(lH,s), 9.05(lH,s) .
Compound 231
1H-NMR(CDCl3) δ: 1.70(3H,d), 2.55(3H,s), 3.77(3H,s),
5.46(lH,q), 8.14(lH,s), 8.48(lH,s), 9.06(lH,s) .
Compound 232 1H-NMR(CDCl3) δ: 1.12 (3H,t) , 2.02-2.12 (2H,m) , 2.55 (3H, s) ,
3.76 (3H, s) , 5.30 (lH,t) , 8.14 (lH, s) , 8.47 (lH, s) , 9.05 (lH, s) .
Compound 233
1H-NMR(CDCl3) δ: 1.01(3H,t), 1.27(3H,t), 1.51-1.64 (2H,m) , 1.91-2.11 (2H, m) , 2.54(3H,s), 4.22(2H,q), 5.32(lH,dd),
8.14(1H, s), 8.46(lH,s), 9.05(lH,s) .
Compound 234
1H-NMR(CDCl3) δ: 1.18(3H,t), 1.74(6H,s), 2.49(3H,s),
4.18(2H,q), 8.13(lH,s), 8.43(lH,s), 9.03(lH,s) . Compound 235
1H-NMR(CDCl3) δ: 1.15(3H,t), 2.53-2.58 ( 5H, m) , 5.07(2H,s),
8.14(lH,s), 8.45(lH,s), 9.06(lH,s).
Compound 236
1H-NMR(CDCl3) δ: l.ll(3H,t), 1.96-2.16 (2H,m) , 2.53(3H,s), 4.65(2H,t), 8.15(lH,s), 8.54(lH,s), 9.09(lH,s) .
Compound 237
1H-NMR(CDCl3) δ: 1.24(3H,t), 2.36(2H,q), 4.89(2H,s),
7.35(lH,s), 8.12(lH,s), 8.67(lH,s), 9.19(lH,s) .
Compound 238 1H-NMR(CDCl3) δ: 1.25(3H,t), 2.37(2H,q), 2.54(3H,s),
4.87(2H,s), 8.15(lH,s), 8.54(lH,s), 9.09(lH,s) .
Compound 239
1H-NMR(CDCl3) δ: 1.26(3H,t), 2.42(2H,q), 4.95(2H,s),
8.21(lH,s), 8.61(lH,s), 9.07(lH,s) . Compound 240
1H-NMR(CDCl3) δ: 1.22(6H,d), 2.53-2.55 (3H,m) , 2.59-2.68 (IH, m) ,
4.90(2H,s), 8.15(lH,s), 8.54(lH,s), 9.09(lH,s) .
Compound 241
1H-NMR(CDCl3) δ: 1.23(6H,d), 2.67-2.74 (IH, m) , 4.99(2H,s), 8.21 (lH, s) , 8.61 (lH, s) , 9.07 (lH, s) .
Compound 242
1H-NMR(CDCl3) δ: 1.21(6H,d), 2.57-2.67 (IH, m) , 4.92(2H,s),
7.34(lH,s), 8.13(1H, s), 8.67(lH,s), 9.19(lH,s) . Compound 243
1H-NMR(CDCl3) δ: 2.51(3H,s), 3.06(3H,s), 3.55(2H,t),
4.96(2H,t), 8.14(1H, s), 8.56(lH,s), 9.09(lH,s) .
Compound 244
1H-NMR(CDCl3) δ: 2.42(2H,dd), 2.48(3H,s), 2.98(3H,s), 3.23(2H,dd), 4.62(2H,t), 8.14(lH,s), 8.53(lH,s), 9.07(lH,s) .
Compound 245
1H-NMR(CDCl3) δ: 1.98-2.15 (4H,m) , 2.47(3H,s), 2.94(3H,s),
3.13(2H,dd), 4.51(2H,t), 8.13(lH,s), 8.52(lH,s), 9.05(lH,s) .
Compound 246 1H-NMR(CDCl3) δ: 2.49(3H,s), 2.71(3H,s), 3.09-3.18 (IH, m) ,
3.20-3.30(lH,m) , 4.86-5.01 (2H,m) , 8.14(lH,s), 8.54(lH,s),
9.07 (IH, s) .
Compound 247
1H-NMR(CDCl3) δ: 1.26(2H,t), 1.96-2.04 (2H,m) , 2.47(3H,s), 2.60(3H,s), 2.69-2.88 (2H,m) , 4.46-4.56 (2H,m) , 8.13(lH,s),
8.52 (IH, s) , 9.05(1H, s) .
Compound 248
1H-NMR(CDCl3) δ: 2.48(3H,s), 3.34(2H,t), 4.72(2H,t),
8.13(lH,s), 8.53(lH,s), 9.07(lH,s) . Compound 249
1H-NMR(CDCl3) δ: 1.23-1.30 (3H,m) , 2.54(3H,s), 3.73-3.86 (IH, m) ,
3.91-4.01 (IH, m) , 4.04-4.16 (IH, m) , 4.74-4.95 (2H,m) ,
8.15(1H, s), 8.56(lH,s), 9.10(lH,s) .
Compound 250 1H-NMR(CDCl3) δ: 1.27(3H,t), 2.13-2.22 (2H,m) , 2.46(3H,s), 2.51(2H,t), 4.16(2H,q), 4.50(2H,t), 8.13(lH,s), 8.51(lH,s), 9.04 (IH, s) . Compound 251 1H-NMR(CDCl3) δ: 1.59(3H,d), 2.24(3H,s), 2.55(3H,s), 5.44(lH,q), 8.14(lH,s), 8.45(lH,s), 9.06(lH,s).
Formulation Examples will be shown below. Parts means parts by weight. Formulation Example 1
Ten (10) parts of each of the compounds (1) to (251) is dissolved in a mixture of 35 parts of xylene and 35 parts of N, N-dimethylformamide, and 14 parts of polyoxyethylene styryl phenyl ether and 6 parts of calcium dodecylbenzenesulfonate are added thereto, followed by well stirring, to obtain 10% emulsions for each compound.
Formulation Example 2
Twenty. (20) parts of each of the compounds (1) to (251) is added to a mixture containing 4 parts of sodium lauryl sulfate, 2 parts of calcium lignin sulfonate, 20 parts of a synthetic hydrated silicone oxide fine powder and 54 parts of diatomite, followed by well stirring, to obtain 20% wettable powders for each compound.
Formulation Example 3
To 2 parts of each of the compounds (1) to (251) are added 1 part of a synthetic hydrated silicon oxide fine powder, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay, followed by well stirring, and an appropriate amount of water is added to the mixture, followed by granulating with a granulator, and air drying, to give 2% granules for each compound.
Formulation Example 4
One (1) part of each of the compounds (1) to (251) is dissolved in an appropriate amount of acetone, and 5 parts of a synthetic hydrated silicon oxide fine powder, 0.3 parts of PAP, and 93.7 parts of Fubasami clay are well stirring and mixing, and acetone is removed by evaporation from the mixture, to give 1% powders for each compound.
Formulation Example 5 , Ten (10) parts of each of the compounds (1) to (251), 35 parts of white carbon containing 50 parts of a polyoxyethylene alkyl ether sulfate ammonium salt, and 55 parts of water are mixed and pulverized by a wet grinding method to give 10% flowables for each compound.
Formulation Example 6
Zero point one (0.1) parts of each of the compounds (1) to (251) is dissolved in a mixture of 5 parts of xylene and 5 parts of trichloroethane, and the resulting solution is mixed with 89.9 parts of deodorized kerosine to give 0.1% oil solutions for each compound.
Formulation Example 7
Ten (10) mg of each of the compounds (1) to (251) is dissolved in 0.5 ml of acetone, the solution is applied to 5 g of powdery solid animal food (powdery solid animal food for bleeding CE-2; a product of CLEA Japan, Inc.) and mixed uniformly, and acetone is dried by evaporation from the mixture, to give poison baits for each compound.
It is shown by Test Examples that the present compound is effective as an active ingredient of a pest controlling agent.
Test Example 1
The formulation of each of the present compounds (8), (11), (15), (18), (21), (22), (25), (26), (33) to (35), (37), (39), (44), (45), (47) to (49), (51), (52), (55), (60), (61), (65) to (68), (73) to (75), (77), (79), (82) to (89), (91) to (94), (96), (102), (106), (107), (109), (110), (112), (114), (116), (117), (119), (120), (122), (123), (131) to (134), (140), (141), (146), (148) to (150), (152), (156), (180), (188), (189), (190), (195), (196), (199) to (202), (204), (205), (208), (220), (221), (227) to (229), (236) to (238), (240) and (241) obtained in Reference Example 5 was diluted with water so as to adjust the concentration of the active ingredient to 500 ppm, then a test solution was prepared. On a cucumber seedling at 2nd true leaf stage placed in a polyethylene cup, about thirty (30) imagoes of Aphis gossypii were inoculated. One day after inoculation, 10 m of the above test solution was sprayed on the plant.
Five days after spraying, the number of the surviving insects of Aphis gossypii parasited on the leaves of the cucumber seedling and a control value was determined by the following equation.
Control value (%) = {1 - (Cb x Tai)/(Cai x Tb)) x 100 wherein symbols have the following meanings.
Cb: the number of insects in a non-treated section before treatment
Cai: the number of insects in a non-treated section on observation Tb: the number of insects in a treated-section before treatment
Tai: the number of insects in a treated-section on observation
As a result, the treated section of the test solution of each of the present compounds (8), (11), (15), (18), (21), (22), (25), (26), (33) to (35), (37), (39), (44), (45), (47) to (49), (51), (52), (55), (60), (61), (65) to (68), (73) to (75), (77), (79), (82) to (89), (91) to (94), (96), (102), (106), (107), (109), (110), (112), (114), (116), (117), (119), (120), (122), (123), (131) to (134), (140), (141), (146), (148) to (150), (152), (156), (180), (188), (189), (190), (195), (196), (199) to (202), (204), (205), (208), (220), (221), (227) to (229), (236) to (238), (240) and (241) exhibited the control value of 90% or more.
Test Example 2
The formulation of each of the present compounds (3), (6) to (11), (14) to (16), (19) to (23), (25), (26), (33) to (35), (44) to (49), (52), (53), (55), (60), (65), (66), (71) to (73), (75), (77) to (80), (82) to (89), (91) to (95), (100) to (104), (107) to (110), (112) to (114), (116) to (128), (131) to (141), (143), (145), (148) to (150), (152), (155), (159), (162), (167), (169), (172), (176), (178) to (180), (188), (189), (194), (196), (199) to (209), (211), (219) to (221), (223) to (225), (227) to (229), (236) to (238) and (240) to (242) obtained in Reference Example 5 was diluted with water so as to adjust the concentration of the active ingredient to 500 ppm, then a test solution was prepared.
On a tomato seedling at the 3rd true leaf stage placed in a polyethylene cup, imagoes of Bemisia tabaci were released and then made to lay eggs for about 24 hours. The tomato seedling was stored in a greenhouse for 8 days. When instar larvae hatched from eggs of Bemisia tabaci, the above test solution was sprayed in the amount of 10 ml/cup. After storage in a greenhouse at 25°C for 7 days, the number of surviving instar larvae on the tomato leaves was examined and a control value was determined by the following equation. Control value (%) = {1 - (Cb x Tai)/(Cai x Tb) ) x 100 wherein symbols have the following meanings. Cb: the number of insects in a non-treated section before treatment Cai: the number of insects in a non-treated section on observation
Tb: the number of insects in a treated-section before treatment
Tai: the number of insects in a treated-section on observation The treated section of the test solution of each of the present compounds (3), (6) to (11), (14) to (16), (19) to (23), (25), (26), (33) to (35), (44) to (49), (52), (53), (55), (60), (65), (66), (71) to (73), (75), (77) to (80), (82) to (89), (91) to (95), (100) to (104), (107) to (110),
(112) to (114), (116) to (128), (131) to (141), (143), (145), (148) to (150), (152), (155), (159), (162), (167), (169), (172), (176), (178) to (180), (188), (189), (194), (196), (199) to (209), (211), (219) to (221), (223) to (225), (227) to (229), (236) to (238) and (240) to (242) exhibited the control value of 90% or more.
Industrial Applicability
The present compound has a control effect against pests and is useful as an active ingredient of a pest controlling agent.

Claims

1. A pyrimidine compound represented by formula (1) :
Figure imgf000171_0001
wherein
Q represents oxygen or -S(O)n-/ n represents 0, 1 or 2,
G1 represents nitrogen or CR6 ,
R1 , R2 and R6 are the same or different and represent hydrogen, halogen, a nitro group, a cyano group, a C1-C6 chain hydrocarbon group optionally substituted with halogen, -L1R7, -C(=O)R8, a phenyl group optionally substituted with one or more members selected from Group A, or a 5- or 6- aromatic heterocyclic group optionally substituted with one or more members selected from Group A, L1 represents oxygen, -S(O)n- or -NR9-,
R7 represents hydrogen or a chain C1-C6 hydrocarbon group optionally substituted with halogen, provided that R7 is not hydrogen when L1 is -S(O)n- and n is 1 or 2, R8 represents hydrogen, a hydroxy group, an amino group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C1-C6 alkoxy group optionally substituted with halogen, a C1-C4 alkylamino group optionally substituted with halogen, or a C2-C8 dialkylamino group optionally substituted with halogen,
R9 represents hydrogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen or a C1-C6 alkylsulfonyl group optionally substituted with halogen,
R3 represents hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, or - L2R10,
R4 represents hydrogen, halogen, a nitro group, a cyano group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, -L2R10, -Cl=O)R11, a phenyl group optionally substituted with one or more members selected from Group A, or a 5- or 6-membered aromatic heterocyclic group optionally substituted with one or more members selected from Group A, L2 represents oxygen, -S(O)n- or -NR12-,
R10 represents hydrogen or a chain C1-C6 hydrocarbon group optionally substituted with halogen, provided that R10 is not hydrogen when L2 is -S(O)n- and n is 1 or 2, R11 represents hydrogen, a hydroxy group, an amino group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C1-C6 alkoxy group optionally substituted with halogen, a C1-C4 alkylamino group optionally substituted with halogen, or a C2-C8 dialkylamino group optionally substituted with halogen, R12 represents hydrogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or a C1-C6 alkylsulfonyl group optionally substituted with halogen, R5 represents a Cl-ClO alkyl group substituted with one or more members selected from Group B, or a C3-C10 alkenyl group substituted with or one or more members selected from Group B,
Group A represents the group consisting of halogen, an amino group, a cyano group, a nitro group, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a Cl- C6 alkoxy group optionally substituted with halogen, and S(0)nR13, in which R13 represents a C1-C6 alkyl group optionally substituted with halogen, Group B represents the group consisting of halogen, -L3R14 and -C(=O)R15, wherein L3 represents oxygen, -S(O)n-, -NR16- or -Si(R17 )2-, R14 represents hydrogen, or a chain C1-C6 hydrocarbon group optionally substituted with halogen, provided that R14 is not hydrogen when L3 is -S(O)n- and n is 1 or 2, R15 represents hydrogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C1-C4 alkylamino group optionally substituted with halogen, a C2-C8 dialkylamino group optionally substituted with halogen, or a C1-C6 alkoxy group optionally substituted with halogen, R16 represents hydrogen, or a chain C1-C6 hydrocarbon group optionally substituted with halogen,
R17S are the same or different and represents a chain C1-C6 hydrocarbon group optionally substituted with halogen.
2. The pyrimidine compound according to claim 1, wherein R1 , R2 and R6 are the same or different and represent hydrogen, halogen, a nitro group, a cyano group, a chain Cl- C6 hydrocarbon group optionally substituted with halogen, - L1R7 or -C(=O)R8.
3. The pyrimidine compound according to claim 1, wherein R1 , R2 and R6 are the same or different and represent hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, -L1R7 or -C(=O)R8.
4. The pyrimidine compound according to claim 1, wherein R1 and R6 are the same or different and represent hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -C(=O)R8.
5. The pyrimidine compound according to claim 1, wherein R2 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L1R7.
6. The pyrimidine compound according to claim 1, wherein R4 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, a C3-C8 cycloalkyl group optionally substituted with halogen, or -L2R10.
7. The pyrimidine compound according to claim 1, wherein R3 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or a C3-C8 cycloalkyl group optionally substituted with halogen.
8. The pyrimidine compound according to claim 1, wherein R3 is hydrogen.
9. The pyrimidine compound according to claim 1, wherein Q i s oxygen .
10. The pyrimidine compound according to claim 1, wherein R5 is a Cl-ClO alkyl or C3-C10 alkenyl group substituted with halogen or -L3R14.
11. The pyrimidine compound according to claim 1, wherein R5 is a Cl-ClO alkyl or C3-C10 alkenyl group substituted with halogen.
12. The pyrimidine compound according to claim 1, wherein Q is oxygen,
G1 is nitrogen or CR6 ,
R1 and R6 are the same or different and represent hydrogen, halogen or a chain C1-C6 hydrocarbon group optionally substituted with halogen,
R2 is hydrogen, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L1R7,
R3 is hydrogen or a chain C1-C6 hydrocarbon group optionally substituted with halogen,
R4 is hydrogen, halogen or a chain C1-C6 hydrocarbon group optionally substituted with halogen, and
R5 is a Cl-ClO alkyl or C3-C10 alkenyl group substituted with halogen or -L3R14.
13. A pest controlling agent comprising the pyrimidine compound according to claim 1 and an inert carrier.
14. Use of the pyrimidine compound according to claim 1 for controlling pests.
15. A method of controlling pests, which comprises the step of applying an effective amount of the pyrimidine compound according to claim 1 to pests or habitats of the pests.
16. 4-(2,2,3,3-tetrafluoropropoxy) -6- ( [1, 2, 4] triazol-1-yl) - pyrimidine.
17. 5-methyl-4- (2,2,3, 3-tetrafluoropropoxy) -6- ( [1,2, 4] triazol-1-yl) -pyrimidine .
18. 5-chloro-4- (2,2,3, 3-tetrafluoropropoxy) -6- ([1,2, 4] triazol-1-yl) -pyrimidine.
19. 4- (2, 2, 3, 4,4,4-hexafluorobutyloxy)-6- ( [1,2, 4] triazol-1- yl) -pyrimidine .
20. 4- (2,2,3, 4, 4, 4-hexafluorobutyloxy) -5-methyl-6-
( [1,2, 4] triazol-1-yl) -pyrimidine.
21. 5-chloro-4- (2,2,3,4,4, 4-hexafluorobutyloxy) -6- ( [1,2, 4] triazol-1-yl) -pyrimidine .
22. 4- (2, 2, 3, 3, 4, 4, 5, 5-octafluoropentyloxy) -5-methyl-6- ( [1,2, 4] triazol-1-yl) -pyrimidine.
23. 5-chloro-4- (2, 2, 3, 3, 4, 4, 5, 5-octafluoropentyloxy) -6- ( [1, 2,4] triazol-1-yl) -pyrimidine .
24. 4- (2-chloro-2-methylpropoxy) -5-methyl-6- ([1,2, 4] triazol- 1-yl) -pyrimidine.
25. 4- (2, 2-dichloropropoxy) -5-methyl-6- ( [1, 2, 4] triazol-1- yl ) -pyrimidine .
26. A compound represented by formula (4) :
Figure imgf000177_0001
wherein
Q represents oxygen, R3 represents hydrogen,
R4 represents hydrogen, halogen, or a chain C1-C6 hydrocarbon group,
R5 represents a Cl-ClO alkyl group substituted with one or more halogen, or a C3-C10 alkenyl group substituted with one or more halogen.
27 . A compound represented by formula (2) :
Figure imgf000177_0002
wherein
G1 represents nitrogen or CR6 , R6 represents hydrogen,
R1 represents hydrogen, or halogen,
R2 represents hydrogen, halogen, or an amino group,
R3 represents hydrogen,
R4 represents halogen, a nitro group, a cyano group, or a chain C1-C6 hydrocarbon group optionally substituted with halogen.
28. A compound represented by formula (6) :
Figure imgf000178_0001
wherein
G1 represents nitrogen or CR6 , R6 represents hydrogen, R1 represents hydrogen, or halogen, R2 represents hydrogen, halogen, or an amino group, R3 represents hydrogen,
R4 represents halogen, a nitro group, a cyano group, or a chain C1-C6 hydrocarbon group optionally substituted with halogen.
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