WO2010119879A1 - Composé de pyrimidine et son utilisation pour la lutte antiparasitaire - Google Patents

Composé de pyrimidine et son utilisation pour la lutte antiparasitaire Download PDF

Info

Publication number
WO2010119879A1
WO2010119879A1 PCT/JP2010/056629 JP2010056629W WO2010119879A1 WO 2010119879 A1 WO2010119879 A1 WO 2010119879A1 JP 2010056629 W JP2010056629 W JP 2010056629W WO 2010119879 A1 WO2010119879 A1 WO 2010119879A1
Authority
WO
WIPO (PCT)
Prior art keywords
halogen
group
optionally substituted
hydrogen
group optionally
Prior art date
Application number
PCT/JP2010/056629
Other languages
English (en)
Inventor
Hiroki Tomioka
Hajime Mizuno
Daisuke Takaoka
Hiroshi Ikegami
Yoshihiko Nokura
Original Assignee
Sumitomo Chemical Company, Limited
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Sumitomo Chemical Company, Limited filed Critical Sumitomo Chemical Company, Limited
Publication of WO2010119879A1 publication Critical patent/WO2010119879A1/fr

Links

Classifications

    • 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
    • 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, US200/0005403 Al, JP-A-63-039875 and WO 99/41253.
  • 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 formula (1) shown below 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 C1-C6 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 10
  • 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 Cl-C ⁇ hydrocarbon group optionally substituted with halogen, or a C1-C6 alkylsulfonyl group optionally substituted with halogen
  • R 5 represents a C4-C10 alkyl group or a C3-C10 alkenyl group
  • 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- C ⁇ alkoxy group optionally substituted with halogen and S(O) n R 13 , in which that R 13 represents a C1-C6 alkyl group optionally substituted with halogen (hereinafter referred to as the present compound) .
  • 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, halogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or a C3-C8 cycloalkyl group optionally substituted with halogen.
  • R 5 is a branched C4-C10 alkyl group, or a C3- ClO alkenyl group.
  • G 1 is nitrogen or CR 6 ,
  • R 1 and R 6 are the same or different and represent hydrogen, ha logen, or a chain C1-C6 hydrocarbon group optionally subst ituted with halogen,
  • R 2 is hydrogen, halogen, a chain C1-C6 hydrocarbon group opti onally substituted with halogen, or -L 1 R 7 ,
  • R 3 is hydrogen or a chain C1-C6 hydrocarbon group optionally s ubstituted with halogen
  • R 4 is hydrogen, halogen, or a chain C1-C6 hydrocarbon grou p optionally substituted with halogen, and
  • R 5 is a branched C4-C8 alkyl group, or a C3-C8 alkenyl grou
  • a pest controlling agent comprising the pyrimidine compound according to any one of [1] to [11], 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 [11] to pests or habitats of the pests.
  • examples of the "halogen” include 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, a 1- methylbutyl group, a tert-pentyl group, a neopentyl group, a hexyl group and an isohexyl group;
  • 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, a
  • 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
  • C2-C6 alkynyl groups such as an ethynyl group, a 2- propynyl group, a 2-butynyl group and a 3-butynyl group.
  • 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
  • C2-C6 alkynyl groups 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.
  • 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.
  • 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, a 1-pyrrolyl group and a 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 l-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-pyri
  • 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 "C4-C10 alkyl group” includes, for example, linear C4-C10 alkyl groups such as a butyl group, a pentyl group, a hexyl group, a heptyl group and an octyl group; and branched C4-C10 alkyl groups such as an isobutyl group, a sec-butyl group, a tert-butyl group, an isopentyl group, a 1-methylbutyl group, a tert-pentyl group, a neopentyl group, an isohexyl group and a 3, 3-dimethylpentyl group.
  • linear C4-C10 alkyl groups such as a butyl group, a pentyl group, a hexyl group, a heptyl group and an octyl group
  • branched C4-C10 alkyl groups such as an isobutyl group
  • the "C3-C10 alkenyl group” includes, for example, linear C3-C10 alkenyl groups such as a 2-propenyl group, a 2-butenyl group, a 3-butenyl group, a 2-pentenyl group, a 2-hexenyl group, a 2-heptenyl group and a 2-octenyl group; and branched C3-C10 alkenyl groups such as a l-methyl-2- propenyl group, a 2-methyl-2-propenyl group and a 1-methyl- 2-butenyl 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 -C( 0)R 8 .
  • R 3 is hydrogen, a chain C1-C6 hydrocarbon group optionally substituted with halogen, or -L 2 R 10 .
  • 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, -L 2 R 10 or -C( O)R 11 .
  • 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 -CC O)R 11 .
  • 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 -C C 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 Cl- 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 Q is oxygen, G 1 is nitrogen or CR 6 , R 1 is hydrogen, halogen, A chain C1-C6 hydrocarbon group optionally substituted with halogen, -L 1 R 7 or -C( O)R 8 , 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 , and R 5 is a C4-C10 alkyl group or a C3-C10 alkenyl group.
  • the present compound can be produced, for example, by the following (Production Process A) to (Production Process E) .
  • the compound represented by formula (1-i) wherein 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, diethyl ' ether, 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 sul
  • 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.
  • DBU 1, 8-diazabicyclo [5, 4, 0] 7-undecene
  • DBU 1, 8-diazabicyclo [4, 3, 0] 5-nonene
  • tertiary amines such as triethylamine and N, N-
  • 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.
  • 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 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 - Cl O)R 11 .
  • R 3 , R 4 , R 5 and Q' are as defined above (hereinafter referred to as the compound (4)) with the compound represented by formula (5) :
  • 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°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 (4) include, for example, the following pyrimidine compounds.
  • 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 -C C O)R 11 ;
  • R 5 is a branched C3-C10 alkenyl group.
  • the present compound (1-i) can be produced by reacting the compound represented by formula (6) :
  • 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 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 -C C O) R 1 1 .
  • 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 .
  • a pyrimidine compound represented by formula (6), 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 (7) : R 3
  • 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 0 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 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 -C( O)R 1:L .
  • RV VS R 2 ' ⁇ 1" ⁇ wherein 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
  • 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.
  • 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 0 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 (hereinafter referred to as 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.
  • 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.
  • the compound (7) can be isolated by pouring the reaction mixture into water, extracting with an organic solvent and concentrating the organic layer; collecting a solid produced by pouring the reaction mixture into water by filtration; or collecting a solid produced in the reaction mixture by filtration.
  • the isolated compound (7) can further purified by chromatography, distillation and so on.
  • the compound represented by formula (7-ii) wherein 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°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; 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 (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 any one of the combinations shown in Table 1 to Table 3.
  • 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 3.
  • 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 3.
  • 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 3.
  • a compound represented by formula (F) is
  • 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 3.
  • 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 3.
  • 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 3.
  • a compound represented by formula (I) 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 3.
  • R 1 and R 3 represent hydrogen, Q represents sulfur, and R 2 , R 5 , G 1 and R 6 represents any one of the combinations described in Table 1 to Table 3.
  • 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
  • leafhoppers such as green rice leafhopper (Nephotettix cincticeps), green rice leafhopper (Nephotettix virescens) , and tea green leafhopper (Empoasca onukii) ; aphids (Aphididae) such as cotton aphid
  • stink bugs pests such as green stink bug (Nezara antennata) , bean bug (Riptortus clavetus) , rice bug (Leptocorisa chinensis) , white spotted spined bug
  • 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
  • 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 (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 nigrisign
  • 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) ;
  • 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.
  • 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; Simuliida
  • 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
  • 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 ponnes, Pheidole noda, leaf-cutting ant (Acromyrmex spp.) , and fire ant (Solenopsis spp.
  • 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 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 liguid 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, fluorocarbo ns, butane gas, liquefied petroleum gas (LPG) , dimethyl ether , and carbon dioxide.
  • fluorocarbo ns fluorocarbo ns
  • butane gas liquefied petroleum gas (LPG)
  • LPG liquefied petroleum gas
  • dimethyl ether dimethyl ether
  • carbon dioxide 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, and 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, and 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 10000 ppm.
  • 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.
  • 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 1000 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. "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 (J
  • 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,
  • 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 .
  • 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.
  • active ingredients of the insecticide, the acaricide, the nematocide, the fungicide, the plant growth regulator, the herbicide, and the synergist are shown below.
  • Cartap bensultap, thiocyclam, monosultap, bisultap;
  • Neonicotinoid compounds Imidacloprid, nitenpyram, acetamiprid, thiamethoxam, thiacloprid, dinotefuran, clothianidin;
  • Chlorfluazuron bistrifluron, diafenthiuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, triazuron;
  • 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.
  • 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;
  • 2,3,6-TBA dicamba, clopyralid, picloram, aminopyralid, quinclorac, and quinmerac.
  • Triazine herbicidal compounds atrazine, ametoryn, cyanazine, simazine, propazine, simetryn, dimethametryn, prometryn, metribuzin, indaziflam, and triaziflam.
  • Hydroxybenzonitrile herbicidal compounds bromoxynil and ioxynil.
  • Dinitroaniline herbicidal compounds pendimethalin, prodiamine, and trifluralin.
  • Organic phosphorus herbicidal compounds amiprofos-methyl, butamifos, bensulide, piperophos, anilofos, glyphosate, glufosinate, and bialaphos.
  • 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, forams
  • Sulfonamide herbicidal compounds flumetsulam, metosulam, diclosulam, florasulam, cloransulam-methyl, penoxsulam, and pyroxsulam.
  • 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.
  • THF tetrahydrofuran
  • 4 g of 60% sodium hydride (oily) and 14.9 g of 4, 6-dichloropyrimidine r were added under ice cooling.
  • the mixture was stirred at room temperature for 1 hour and then stirred at 70 0 C for 6 hours.
  • Water was poured into the reaction mixture which was cooled to room temperature, followed by extraction with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and then concentrated under reduced pressure.
  • NMP N-methyl pyrrolidone
  • DBU 1, 8-diazabicyclo [5, 4, 0] 7-undecene
  • R 2 wherein R 1 , R 2 , R 3 , R 4 , R 5 , G 1 , R 6 and Q represent the combinations described in Table 4 to Table 6 shown below,
  • Parts means parts by weight.
  • 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 3 To 2 parts of each of the compounds (1) to (69) 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.
  • Test Example 1 Test Example 1
  • 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
  • Tb the number of insects in a treated-section before treatment
  • Tai the number of insects in a treated-section on observation
  • Test Example 2 The formulation of each of the present compounds (1) to (3), (5) to (7), (9), (10), (15), (17) to (19), (22), (25), (26), (28), (30), (33), (34), (36), (38), (39), (41), (42), (44) to (46), (50) to (52), (54), (59), (63), (65) and (66) 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.
  • 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
  • the present compound has a control effect against pests and is useful as an active ingredient of a pest controlling agent.

Abstract

La présente invention concerne un composé de pyrimidine représenté par la formule (1) qui permet de lutter contre les parasites et est utile comme principe actif d'un agent de lutte antiparasitaire.
PCT/JP2010/056629 2009-04-16 2010-04-07 Composé de pyrimidine et son utilisation pour la lutte antiparasitaire WO2010119879A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2009-099737 2009-04-16
JP2009099737 2009-04-16

Publications (1)

Publication Number Publication Date
WO2010119879A1 true WO2010119879A1 (fr) 2010-10-21

Family

ID=42982540

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2010/056629 WO2010119879A1 (fr) 2009-04-16 2010-04-07 Composé de pyrimidine et son utilisation pour la lutte antiparasitaire

Country Status (3)

Country Link
JP (1) JP2010265259A (fr)
AR (1) AR076296A1 (fr)
WO (1) WO2010119879A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012050237A1 (fr) * 2010-10-15 2012-04-19 Sumitomo Chemical Company, Limited Composés de pyrimidine et leur utilisation en tant que pesticides
WO2012073995A1 (fr) * 2010-12-01 2012-06-07 住友化学株式会社 Composé cyclique hétéroaromatique et son application antiparasitaire
US20140249134A1 (en) * 2011-10-06 2014-09-04 Merck Sharp & Dohme Corp. Triazolyl pde10 inhibitors

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2012102090A (ja) * 2010-10-15 2012-05-31 Sumitomo Chemical Co Ltd ピリミジン化合物およびその有害生物防除用途

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6339875A (ja) * 1986-08-05 1988-02-20 Nissin Food Prod Co Ltd ピリミジン誘導体
JPH08503932A (ja) * 1992-09-16 1996-04-30 ゼネカ・リミテッド 駆虫活性を有する複素環式化合物
JP2003267957A (ja) * 2002-03-12 2003-09-25 Sumitomo Chem Co Ltd ピリミジン化合物およびその用途
CN101130521A (zh) * 2007-09-18 2008-02-27 中国农业科学院植物保护研究所 具有明显生物活性的新型嘧啶衍生物
JP2008526793A (ja) * 2005-01-05 2008-07-24 バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト 殺有害生物剤の形態で使用されるアルキニル−オキシピリミジン

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6339875A (ja) * 1986-08-05 1988-02-20 Nissin Food Prod Co Ltd ピリミジン誘導体
JPH08503932A (ja) * 1992-09-16 1996-04-30 ゼネカ・リミテッド 駆虫活性を有する複素環式化合物
JP2003267957A (ja) * 2002-03-12 2003-09-25 Sumitomo Chem Co Ltd ピリミジン化合物およびその用途
JP2008526793A (ja) * 2005-01-05 2008-07-24 バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト 殺有害生物剤の形態で使用されるアルキニル−オキシピリミジン
CN101130521A (zh) * 2007-09-18 2008-02-27 中国农业科学院植物保护研究所 具有明显生物活性的新型嘧啶衍生物

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
IKEDA, M.: "Synthesis and cytoprotective antiulcer activity of 2- or 4-(lH-pyrazol-1-yl)pyrimidine derivatives related to mepirizole and dulcerozine", CHEM PHARM BULL, vol. 44, no. 9, 1996, pages 1700 - 6 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012050237A1 (fr) * 2010-10-15 2012-04-19 Sumitomo Chemical Company, Limited Composés de pyrimidine et leur utilisation en tant que pesticides
WO2012073995A1 (fr) * 2010-12-01 2012-06-07 住友化学株式会社 Composé cyclique hétéroaromatique et son application antiparasitaire
US20140249134A1 (en) * 2011-10-06 2014-09-04 Merck Sharp & Dohme Corp. Triazolyl pde10 inhibitors
US9200001B2 (en) * 2011-10-06 2015-12-01 Merck Sharp & Dohme Corp. Triazolyl PDE10 inhibitors

Also Published As

Publication number Publication date
JP2010265259A (ja) 2010-11-25
AR076296A1 (es) 2011-06-01

Similar Documents

Publication Publication Date Title
EP2486035B1 (fr) Composé hétérocyclique et son utilisation pour lutter contre un arthropode nuisible
EP2646433B1 (fr) Composé pyrimidine et son utilisation pour la lutte antiparasitaire
US8273764B2 (en) Fused heterocyclic compounds and use thereof
AU2013366867B2 (en) Fused oxazole compounds and use thereof for pest control
US20120041009A1 (en) Pyrimidine compound and its use in pest control
US8796306B2 (en) Noxious arthropod controlling composition and heterocyclic compound
EP3018130A1 (fr) Composé hétérocyclique condensé et son utilisation pour lutter contre les ravageurs
CN104334552A (zh) 稠合杂环化合物
WO2012050237A1 (fr) Composés de pyrimidine et leur utilisation en tant que pesticides
CN104395300A (zh) 稠合杂环化合物
EP2955178A1 (fr) Composé hétérocyclique condensé
EP2865665B1 (fr) Composé amide et son utilisation pour la lutte contre les animaux nuisibles
SA516371932B1 (ar) مركب بيريميدين
WO2010119878A1 (fr) Composé de pyrimidine et son utilisation pour la lutte antiparasitaire
WO2011049150A1 (fr) Composé de pyrone et son utilisation pour lutter contre les organismes nuisibles
WO2010119879A1 (fr) Composé de pyrimidine et son utilisation pour la lutte antiparasitaire

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 10764463

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 10764463

Country of ref document: EP

Kind code of ref document: A1