WO2012050237A1 - Composés de pyrimidine et leur utilisation en tant que pesticides - Google Patents

Composés de pyrimidine et leur utilisation en tant que pesticides Download PDF

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Publication number
WO2012050237A1
WO2012050237A1 PCT/JP2011/074232 JP2011074232W WO2012050237A1 WO 2012050237 A1 WO2012050237 A1 WO 2012050237A1 JP 2011074232 W JP2011074232 W JP 2011074232W WO 2012050237 A1 WO2012050237 A1 WO 2012050237A1
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group
optionally substituted
halogens
group optionally
compound
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PCT/JP2011/074232
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Yoshihiko Nokura
Hiroshi Ikegami
Hiroki Tomioka
Daisuke Takaoka
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Sumitomo Chemical Company, Limited
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Publication of WO2012050237A1 publication Critical patent/WO2012050237A1/fr

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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
    • C07D403/02—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
    • 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
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings

Definitions

  • the present invention relates to a pyrimidine compound and use thereof for controlling pests.
  • Some compounds exhibiting a pest control activity have been discovered and developed as an active ingredient of a pesticidal agent.
  • some types of pyrimidine compounds are known as an active ingredient thereof (see, for example, Patent References 1 to 3) .
  • the purpose of the present invention is to provide a novel compound having a pest control activity.
  • the present inventors have extensively studied to find a compound exhibiting a pest control activity, and then have found that a pyrimidine compound of the following Formula (1) exhibits an excellent activity in controlling pests. Based upon the new findings, the present invention has been completed.
  • the present inventions are as follows.
  • a pyrimidine compound of Formula (1) [1] A pyrimidine compound of Formula (1) :
  • R 1 is C1-C3 chain hydrocarbon group optionally substituted with one or more halogens, hydrogen, halogen or amino group,
  • R 2 is C1-C3 chain hydrocarbon group optionally substituted with one or more halogens, hydrogen, halogen, hydroxy group, mercapto group or amino group,
  • R 3 is C1-C3 chain hydrocarbon group optionally substituted with one or more halogens, hydrogen, halogen, amino group, nitro group or cyano group,
  • R 4 is C1-C6 chain .
  • hydrocarbon group optionally substituted with one or more halogens, C3-C8 cycloalkyl group optionally substituted with one or more halogens, Cl- C6 alkoxy group .
  • Q is oxygen or -S(0) r - wherein r is 0, 1 or 2,
  • A is a single bond, methylene group optionally substituted with one or more atoms or groups selected from the group consisting of C1-C3 alkyl group and halogen, or ethylene group optionally substituted with one or more atoms or groups selected from the group consisting of C1-C3 alkyl group and halogen, and A is attached to the carbon atom of the ring defined as Cyc,
  • Group a consists of C1-C6 chain hydrocarbon group optionally substituted with one or more halogens, C1-C6 alkoxy group optionally substituted with one or more halogens, C1-C6 alkylthio group optionally substituted with one or more halogens, C1-C6 alkylsulfinyl group optionally substituted with one or more halogens, C1-C6 alkylsulfonyl group optionally substituted with one or more halogens, Cl- C6 alkylamino group optionally substituted with one or more halogens, C2-C8 dialkylamino group optionally substituted with one or more halogens, halogen, hydroxy group, mercapto group, amino group, cyano group and nitro group,
  • Group ⁇ consists of C1-C6 chain hydrocarbon group optionally substituted with one or more halogens, C1-C6 alkoxy group optionally substituted with one or more halogens, C1-C6 alkylthio group optionally substituted with one or more halogens, C1-C6 alkylsulfinyl group optionally substituted with one or more halogens, C1-C6 alkylsulfonyl group optionally substituted with one or more halogens, Cl- C6 alkylamino group optionally substituted with one or more halogens, C2-C8 dialkylamino group optionally substituted with one or more halogens, C2-C6 alkylcarbonylamino group optionally substituted with one or more halogens, C2-C6 alkoxycarbonylamino group optionally substituted with one or more halogens, C2-C6 alkylcarbonyl group optionally substituted with one or more halogens, C2-
  • R 7 is C1-C3 alkyl group optionally substituted with one or more halogens or hydrogen
  • X 1 and X 2 are independently selected from the group consisting of oxygen and sulfur
  • T 1 is methylene group optionally substituted with one or more halogens or ethylene group optionally substituted with one or more halogens
  • Group ⁇ 3 consists of bivalent radicals shown by -T 2 - and -X 3 -T 3 -X 4 - wherein X 3 and X 4 are independently selected from the group consisting of oxygen and sulfur, and T 2 and T 3 are independently selected from the group consisting of methylene group optionally substituted with one or more halogens,
  • R is halogen
  • R 9 and R 10 are independently selected from the group consisting of C1-C3 alkyl group optionally substituted with one or more halogens, and halogen,
  • p is an integer, of 0 to 9, provided , that when p is an integer of 2 to 9, each R 9 may be different from each other, q is an integer of 0 to 8, provided that when q is an integer of 2 to 8, each R 10 may be different from each other, and
  • R 1 , R 2 , R 3 , R 4 and G 1 are as defined above, and Z is halogen .
  • R 1 is hydrogen
  • R 2 is hydrogen or amino group
  • R 3 is hydrogen
  • R 4 is C1-C6 chain hydrocarbon group optionally substituted with one or more halogens, C1-C6 alkoxy group optionally substituted with one or more halogens, hydrogen, or halogen,
  • Cyc may be optionally substituted with one or more atoms or groups selected from the following Groups ⁇ to ⁇ 3,
  • A is a single bond, methylene group optionally substituted with C1-C3 alkyl group, or ethylene group optionally substituted with C1-C3 alkyl group,
  • Group ⁇ consists of C1-C6 chain hydrocarbon group optionally substituted with one or more halogens, C1-C6 alkoxy group optionally substituted with one or more halogens, C2-C6 alkoxycarbonyl group optionally substituted with one or more halogens, halogen, hydroxy group, and cyano group,
  • Group ⁇ 3 consists of a bivalent radical shown by -T 2 - wherein T 2 is methylene group optionally substituted with one or more halogens .
  • R 1 is hydrogen
  • R 2 is hydrogen
  • R 3 is hydrogen
  • R 4 is C1-C6 chain hydrocarbon group, hydrogen, or halogen
  • Cyc may be optionally substituted with one or more atoms or groups selected from the following Groups ⁇ to ⁇ 3,
  • A is a single bond, methylene group optionally substituted with C1-C3 alkyl group, or ethylene group optionally substituted with C1-C3 alkyl group,
  • Group ⁇ consists of C1-C6 chain hydrocarbon group optionally substituted with one or more halogens, C1-C6 alkoxy group, C2-C6 alkoxycarbonyl group, halogen, hydroxy group, and cyano group
  • Group ⁇ 3 consists of a bivalent radical shown by -T 2 - wherein T 2 is methylene group optionally substituted with one or more halogens.
  • a pesticidal composition comprising the pyrimidine compound of any one of [1] to [13] and an inert carrier.
  • a method for controlling pests which comprises a step of applying an effective amount of the pyrimidine compound of any one of [1] to [13] to pests or habitats thereof.
  • the present compound is useful as an active ingredient of a pesticidal agent because the compound has an excellent activity in controlling pests.
  • halogen used herein includes fluorine, chlorine, bromine and iodine.
  • C2-C6 in “C2-C6 alkoxycarbonyl group” means the total number of carbon atoms in the alkoxycarbonyl group.
  • C1-C3 chain hydrocarbon group used herein includes, for example, C1-C3 alkyl group such as methyl group, ethyl group, .propyl group and isopropyl group; C2-C3 alkenyl group such as vinyl group and 2-propenyl group; and C2-C3 alkynyl group such as ethynyl group and 2-propynyl group.
  • C1-C3 chain hydrocarbon group optionally substituted with one or more halogens used herein includes, for example, C1-C3 alkyl group optionally substituted with one or more halogens such as methyl group, ethyl group, propyl group, isopropyl group, difluoromethyl group, trifluoromethyl group, dichloromethyl group, trichloro- methyl group, 2, 2, 2-trifluoroethyl group, 2 , 2 , 2-trichloro- ethyl group, pentafluoroethyl group and perfluoropropyl group; C2-C3 alkenyl group optionally substituted with one or more halogens such as vinyl group, 2-propenyl group, 2 , 2-dichlorovinyl group and 3-chloro-2-propenyl group; and C2-C3 alkynyl group optionally substituted with one or more halogens such as ethynyl group and 2-propyl
  • C1-C6 chain hydrocarbon group used herein includes, for example, C1-C6 alkyl group such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, isopentyl group, 1-methylbutyl group, tert- pentyl group, neopentyl group, hexyl group and isohexyl group; C2-C6 alkenyl group such as vinyl group, 2-propenyl group, 2-butenyl group, 3-butenyl group, 2-methyl-2- propenyl group, 3-methyl-2-butenyl group, 2-pentenyl group and 2-hexenyl group; C2-C6 alkynyl group such as ethynyl group, 2-propynyl group, 2-butynyl group and 3-butynyl group .
  • C1-C6 chain hydrocarbon group optionally substituted with one or more halogens used herein includes, for example, C1-C6 alkyl group optionally substituted with one or more halogens such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, isopentyl group, 1-methylbutyl group, tert-pentyl group, neopentyl group, hexyl group, isohexyl group, difluoromethyl group, trifluoromethyl group, dichloromethyl group, trichloro- methyl group, 2 , 2 , 2-trifluoroethyl group, 2 , 2 , 2-trichloro- ethyl group, pentafluoroethyl group, perfluoropropyl group, perfluorobutyl group
  • C3-C8 cycloalkyl group optionally substituted with one or more halogens used herein includes, for example, cyclopropyl group, 2 , 2-difluorocyclopropyl group, 2 , 2-dichlorocyclopropyl group, 2 , 2-dibromocyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group and cyclooctyl group.
  • C1-C6 alkoxy group optionally substituted with one or more halogens used herein includes, for example, methoxy group, trifluoromethoxy group, ethoxy group, 2,2,2- trifluoroethoxy group, propyloxy group, isopropyloxy group, butoxy group, isobutyloxy group, sec-butyloxy group, tert- butyloxy group, pentyloxy group and hexyloxy group.
  • C1-C6 alkylthio group optionally substituted with one or more halogens includes, for example, methylthio group, trifluorpmethylthio group, ethylthio group, 2 , 2 , 2-trifluoroethylthio group, propylthio group, isopropylthio group, butylthio group, isobutylthio group, sec-butylthio group, tert-butylthio group, pentylthio group and hexylthio group.
  • C1-C6 alkylsulfinyl group optionally substituted with one or more halogens includes, for example, methylsulfinyl group, trifluoromethyl sulfinyl group, ethylsulfinyl group, 2 , 2 , 2-trifluoro ethylsulfinyl group, propylsulfinyl group, isopropylsulfinyl group, butylsulfinyl group, isobutylsulfinyl group, sec- butylsulfinyl group, tert-butylsulfinyl group, pentyl- sulfinyl group and hexylsulfinyl group.
  • C1-C6 alkylsulfonyl group optionally substituted with one or more halogens includes, for example, methylsulfonyl group, trifluoromethyl sulfonyl group and ethylsulfonyl group.
  • C1-C6 alkylamino group optionally substituted with one or more halogens used herein includes, for example, methylamino group, ethylamino group, 2,2,2- trifluoroethylamino group, propylamino group, isopropyl- amino group, butylamino group, pentylamino group and hexylamino group.
  • C2-C8 dialkylamino group optionally substituted with one or more halogens used herein includes, for example, dimethylamino group, diethylamino group, , bis (2, 2, 2-trifluoroethyl ) amino group, and dipropylamino group.
  • C2-C6 alkylcarbonylamino group optionally substituted with one or more halogens used herein includes, for example, acetylamino group, propionylamino group, butanoylamino group, pentanoylamino group, 2,2,2- trifluoroacetylamino group and 2 , 2 , 2-trichloroacetylamino group.
  • C2-C6 alkoxycarbonylamino group optionally substituted with one or more halogens used .herein includes, for example, methoxycarbonylamino group, ethoxycarbonyl- amino group, propoxycarbonylamino group, tert-butoxy- carbonylamino group and 2 , 2 , 2-trichloroethoxycarbonylamino group .
  • C2-C6 alkylcarbamoyl group optionally substituted with one or more halogens used herein includes, for example, methylcarbamoyl group, ethylcarbamoyl group and 2 , 2 , 2-trifluoroethylcarbamoyl group.
  • C2-C8 . dialkylcarbamoyl group optionally substituted with one or more halogens used herein includes, for example, dimethylcarbamoyl group, diethylcarbamoyl group and dipropylcarbamoyl group.
  • methylene group optionally substituted with one or more atoms or groups selected from the group consisting of C1-C3 alkyl group and halogen used herein includes, for example, methylene group, (methyl ) methylene group, (ethyl) methylene group, difluoromethylene group and dichloromethylene group.
  • ethylene group optionally substituted with one or more atoms or groups selected from the group consisting of C1-C3 alkyl group and halogen used herein includes, for example, ethylene group, 1-methylethylene group, 2- methylethylene group, 1 , 1-dimethylethylene group and 2,2- difluoroethylene group.
  • C2-C6 alkylcarbonyl group optionally substituted with one or more halogens used herein includes, for example, acetyl group, propionyl group, butanoyl group, pentanoyl group and 2 , 2 , 2-trifluoroacetyl group.
  • C2-C6 alkoxycarbonyl group optionally substituted with one or more halogens used herein includes, for example, methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, 2 , 2 , 2-trifluoroethoxycarbonyl group and tert-butoxycarbonyl group.
  • phenyl group optionally substituted with one or more atoms or groups selected from Group a includes, for example, phenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 2-aminophenyl group, 3-aminophenyl group, 4-aminophenyl group, 2- cyanophenyl group, 3-cyanophenyl group, -cyanophenyl group, 2-nitrophenyl group, 3-nitrophenyl group, 4-nitrophenyl group, 2-methylphenyl group, 3-methylphenyl group, 4- methylphenyl group, 2- ( trifluoromethyl ) phenyl group, 3- (trifluoromethyl) phenyl group, 4- (trifluoromethyl ) phenyl group, 2-methoxyphenyl group, 3-methoxyphenyl group, 4- methoxyphenyl group, 4- (trifluoromethoxy) phenyl group, 4- (methylthio)
  • the "5- to 6-membered aromatic heterocyclic group" used herein includes, for example, 2-pyrrolyl group, 2- furyl group, 3-furyl group, 2-thienyl group, 3-thienyl group, 5-pyraz.olyl group, 4-pyrazolyl group, 2-pyridinyl group, 3-pyridinyl group, 4-pyridinyl group, pyrazinyl group, 1-pyrrolyl group and 1-pyrazolyl group.
  • the "5- to 6-membered aromatic heterocyclic group optionally substituted with one or more atoms or groups selected from Group a" used herein includes, for example, l-methyl-2-pyrrolyl group, 2-furyl group, 3-furyl group, 5- bromo-2-furyl group, 5-nitro-2-furyl group, 2-methyl-3- furyl group, 2 , 5-dimethyl-3-furyl group, 2 , 4 -dimethyl-3- furyl group, 2-thienyl group, 3-thienyl group, 5-methyl-2- thienyl group, 3-methyl-2-thienyl group, l-methyl-3- trifluoromethyl-5-pyrazolyl group, 5-chloro-l , 3-dimethyl-4- pyrazolyl group, 2-pyridinyl group, 3-pyridinyl group, 4- pyridinyl group, 2-methyl-3-pyridinyl group, 6-methyl-3- pyridinyl group, 2-chloro-3-pyridin
  • the "3- to 8-membered saturated heterocyclic group containing one atom or group selected from the group consisting of oxygen, -S( 0) n - and -NR 6 - as a .
  • ring component used herein includes, for example, epoxy group, oxetan-2-yl group, oxetan-3-yl group, tetrahydrofuran-2-yl group, tetrahydrofuran-3-yl group,, tetrahydrothiophen-2-yl group, tetrahydrothiophen-3-yl group, tetrahydropyran-2-yl group, tetrahydropyran-3-yl group, tetrahydropyran- -yl group, tetrahydrothiopyran-3-yl group, tetrahydrothiopyran- 4-yl group, l-oxotetrahydrothiophen-4 -yl group, 1,1-dio
  • C3-C8 cycloalkyl group used herein includes, for example, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group and cyclooctyl group.
  • C5-C8 cycloalkenyl group used herein is a 5- to 8-membered unsaturated carbocyclic group having one or more double bonds but less than the maximum allowable double bonds, and specific examples thereof include 1- cyclopentenyl group, 2-cyclopentenyl group, 3-cyclopentenyl group, 1-cyclohexenyl group, 2-cyclohexenyl group, 3- cyclohexenyl group, 1-cycloheptenyl group, 2-cycloheptenyl group, 3-cycloheptenyl group and 4-cycloheptenyl group.
  • the following structures are examples of a cyclohexyl group substituted with two atoms or groups selected from Group ⁇ .
  • the "5- to 8-membered saturated heterocyclic group containing two atoms or groups selected from the group consisting of oxygen, -S( 0) n - and -NR 6 - as a ring component wherein the 5- to 8-membered saturated heterocyclic group may be optionally substituted with one or more atoms or groups selected from Groups ⁇ to ⁇ 3" used herein includes, for example, 1 , 3-dioxolan-4-yl group and 2 , 2-dimethyl-l , 3-dioxolan-4-yl group..
  • C3-C8 cycloalkyl group optionally substituted with one or more atoms or groups selected from Groups ⁇ to ⁇ 3 used herein includes, for example, C3-C8 cycloalkyl group optionally substituted with one or more atoms or groups selected from Group ⁇ such as cyclopropyl group, 2 , 2-difluorocyclopropyl group, 2 , 2-dichlorocyclopropyl group, 2 , 2-dibromocyclopropyl group, cyclobutyl group, cyclopentyl group, 3 , 3-difluorocyclopentyl group, 3,3- dichlorocyclopentyl group, cyclohexyl group, 3- fluorocyclohexyl group, 3-chlorocyclohexyl group, 3,3- difluorocyclohexyl group, 3 , 3-dichlorocyclohexyl group, 4- fluorocyclohexyl group, 4-
  • C3-C8 cycloalkyl group optionally substituted with one or more groups selected from Group ⁇ 2 such as 4-oxycyclohexyl group, 1,4- dioxaspiro [ 4.5] decan-8-yl group, 1 , 4 -dithiaspiro [ 4.5 ] decan- 8-yl group and 4- (methoxyimino) cyclohexyl group;
  • C3-C8 cycloalkyl group optionally substituted with one or more groups selected from Group ⁇ 3 such as 7 , 7-difluoro- bicyclo [ 4.1.0] heptan-3-yl group and 7 , 7-difluoro- bicyclo [ 4.1.0] heptan-2-yl group.
  • the "C5-C8 cycloalkenyl . group optionally substituted with one or more atoms or groups selected from Groups ⁇ to ⁇ 3" used herein includes, for example, 2-cyclopentenyl group, 3-fluoro-2-cyclopentenyl group, 3-chloro-2- cyclopentenyl group, 2-cyclohexenyl group, 3-cyclohexenyl group, 3-fluoro-2-cyclohexenyl group, 3-chloro-2- cyclohexenyl group, 4-fluoro-3-cyclohexenyl group and 4- chloro-3-cyclohexenyl group.
  • the present compound includes, for example, the following pyrimidine compounds.
  • a pyrimidine compound of Formula (1) wherein R 1 is hydrogen, R 2 is hydrogen or amino group, G 1 is nitrogen or -CR 5 , and R 5 is hydrogen.
  • a pyrimidine compound of Formula (1) wherein R 1 is hydrogen, R 2 is hydrogen, G 1 is nitrogen or -CR 5 , and R 5 is hydrogen.
  • a pyrimidine compound of Formula (1) wherein R 1 is hydrogen, R 2 is hydrogen, G 1 is -CR 5 , and R 5 is hydrogen.
  • a pyrimidine compound of Formula (1) wherein R 4 is methyl group is a pyrimidine compound of Formula (1) wherein R 4 is methyl group .
  • a pyrimidine compound of Formula (1) wherein Cyc is 3- to 8-membered saturated heterocyclic group containing one atom or group selected from the group consisting of oxygen, -S( 0) n - and -NR 6 - as a ring component wherein R 6 is as defined above, and the 3- to 8-membered saturated heterocyclic group may be optionally substituted with one or more atoms or groups selected from Groups ⁇ to ⁇ 3; C3- C8 cycloalkyl group optionally substituted with one or more atoms or groups selected from Groups ⁇ to ⁇ 3; or C5-C8 cycloalkenyl group optionally substituted with one or more atoms or groups selected from Groups ⁇ to ⁇ 3.
  • a pyrimidine compound of Formula (1) wherein Cyc is 3- to 8-membered saturated heterocyclic group containing one atom or group selected from the group consisting of oxygen, -S( 0) n - and -NR 6 - as a ring component wherein R 6 is as defined above, and the 3- to 8-membered saturated heterocyclic group may be optionally substituted with one or more atoms or groups selected from Groups ⁇ to ⁇ 3; C3- C8 cycloalkyl group optionally substituted with one or more atoms or groups selected from Groups ⁇ to ⁇ 3; or C5-C8 cycloalkenyl group optionally substituted with one or more atoms or groups selected from Groups ⁇ to ⁇ 3.
  • a pyrimidine compound of Formula (1) wherein Cyc is 3- to 8-membered saturated heterocyclic group containing one atom or group selected from the group consisting of oxygen, -S( 0) n - and -NR 6 - as a ring component wherein R 6 is as defined above, and the 3- to 8-membered.
  • saturated heterocyclic group may be optionally substituted with one or more atoms or groups selected from the group consisting of C1-C3 alkyl group optionally substituted with one or more halogens, and halogen; C3-C8 cycloalkyl group optionally substituted with one or more halogens; or C5-C8 cycloalkenyl group optionally substituted with one or more halogens.
  • a pyrimidine compound of Formula (1) wherein Cyc is 3- to 6-membered saturated heterocyclic group containing one atom or group selected from the group consisting of oxygen, -S( 0) n - and -NR 6 - as a ring component wherein R 6 is as defined above, and the 3- to 6-membered saturated heterocyclic group may be optionally substituted with one or more atoms or groups selected from the group consisting of C.1-C3 alkyl group optionally substituted with one or more halogens, and halogen; C3-C6 cycloalkyl group optionally substituted with one or more halogens; or C5-C6 cycloalkenyl group optionally substituted with one or more halogens.
  • a pyrimidine compound of Formula (1) wherein Cyc is 3-, to 6-membered saturated heterocyclic group containing one group selected from the group consisting of -S( 0) n - and - NR 6 - as a ring component wherein R 6 is as defined above, and the 3- to 6-membered saturated heterocyclic group may be optionally substituted with one or more atoms or groups selected from the group consisting of C1-C3 alkyl group optionally substituted with one or more halogens, and halogen; C3-C6 cycloalkyl group optionally substituted with one or more halogens; or C5-C6 cycloalkenyl group optionally substituted with one or more halogens.
  • a pyrimidine compound of Formula (1) wherein Cyc is 3- to 6-membered saturated heterocyclic group containing one group selected from the group consisting of -S( 0) n - and - NR 6 - as a ring component wherein R 6 is as defined above, and the 3- to 6-membered saturated heterocyclic group may be optionally substituted with one or more atoms or groups selected from the group consisting of C1-C3 alkyl group optionally substituted with one or more fluorine atoms, fluorine and chlorine; C3-C6 cycloalkyl group optionally substituted with one or more fluorine or chlorine atoms; or C5-C6 cycloalkenyl group optionally substituted with one or more fluorine or chlorine atoms.
  • a pyrimidine compound of .Formula (1) wherein Cyc is 3- to 6-membered saturated heterocyclic group containing one - S( 0) n ⁇ as a ring component wherein the 3- to 6-membered saturated heterocyclic group may be optionally substituted with one or more atoms or groups selected from the group consisting of C1-C3 alkyl group optionally substituted with one or more fluorine atoms, fluorine and chlorine; C3-C6 cycloalkyl group optionally substituted with one or more fluorine or chlorine atoms; or C5-C6 cycloalkenyl group optionally substituted with one or more fluorine or chlorine atoms .
  • a pyrimidine compound of Formula (1) wherein Cyc is a group of Jl, p is 0, and Y is -S( 0) n -.or CR 1:L R 12 wherein n is 0, 1 or 2, R 11 is fluorine or chlorine, and R 12 is hydrogen, fluorine or chlorine.
  • a pyrimidine compound of Formula (1) wherein Cyc is a group of Jl, p is 0, Y is -S( 0) n -, and n is 0, 1 or . 2.
  • a pyrimidine compound of Formula (1) wherein Cyc is a group of Jl, p is 0, Y is -S( 0) n -, and n is 0.
  • a pyrimidine compound of Formula (1) wherein Cyc is a group of Jl, p is 0, Y is -S( 0) n -, and n is 1.
  • a pyrimidine compound of Formula (1) wherein Cyc is a group of Jl, p is 0, Y is -S( 0) n -, and n is 2.
  • a pyrimidine compound of Formula (1) wherein A is a single bond; Cyc is a group of Jl or J2; R 8 is fluorine or chlorine; R 9 and R 10 are independently selected from the group consisting of C1-C3 alkyl group. optionally substituted with fluorine or chlorine, fluorine and chlorine; and is -S( 0) n - or CR R 12 wherein is 0, 1 or 2, R 11 is fluorine or chlorine, and R 12 is hydrogen, fluorine or chlorine.
  • a pyrimidine compound of Formula (1) wherein A is a single bond; Cyc is a group of Jl; R 9 is C1-C3 alkyl group optionally substituted with fluorine or chlorine, fluorine, or chlorine; p is an integer of 0 to 2; and Y is -S( 0) n _ or -CR 1]" R 12 - wherein n is 0, 1 or 2, R 11 is fluorine or chlorine, and R 12 is hydrogen, fluorine or chlorine.
  • a pyrimidine compound of Formula (1) wherein A is a single bond; Cyc is a group of Jl; R 9 is C1-C3 alkyl group optionally substituted with fluorine or fluorine; p is an integer of 0 to 2; and Y is -S( 0) n - or -CR 1:L R 12 - wherein n is 0, 1 or 2, R 11 is fluorine, and R 12 is hydrogen or fluorine .
  • a pyrimidine compound of Formula (1) wherein A is a single bond; Cyc is a group of Jl; R 9 is C1-C3 alkyl group optionally substituted with chlorine or chlorine; p is an integer of 0 to 2; and Y is -S( 0) n - or -CR T - wherein n is 0, 1 or 2, R 11 is chlorine, and R 12 is hydrogen or chlorine.
  • a pyrimidine compound of Formula (1) wherein A is a single bond, Cyc is a group of Jl, p is 0, and Y is - S( 0) n - or CR 1:L R 12 wherein n is 0, 1 or 2, .
  • R 11 is fluorine or chlorine, and R 12 is hydrogen, fluorine or chlorine.
  • a pyrimidine compound of Formula (1) wherein A is a single bond, Cyc is a group of Jl, p is 0, Y is -S ⁇ 0) n - r and n is 0, 1 or 2.
  • R 2 is -hydrogen or amino group
  • R 3 is hydrogen
  • R 4 is C1-C6 alkyl group optionally substituted with one or more halogens, C1-C6 alkoxy group optionally substituted with one or more halogens, hydrogen, halogen, amino group, nitro group or cyano group;
  • a pyrimidine compound of Formula (1) wherein Q is oxygen; R 1 is hydrogen; R 2 is hydrogen or amino group; G 1 is nitrogen or -CR 5 wherein R 5 is hydrogen; R 3 is hydrogen; R 4 is C1-C6 alkyl group optionally substituted with one or more halogens, C1-C6 alkoxy group optionally substituted with one or more halogens, hydrogen, halogen, amino group, nitro group or cyano group; and Cyc is a group of Jl or J2.
  • R 1 is hydrogen
  • R 2 is hydrogen or amino group
  • R 3 is hydrogen
  • R 4 is hydrogen, fluorine, chlorine, bromine, iodine, amino group, methyl group, ethyl group or methoxy group
  • a pyrimidine compound of Formula (1) wherein Q is oxygen; R 1 is hydrogen; R 2 is hydrogen or amino group; G 1 is nitrogen or -CR 5 wherein R 5 is hydrogen; R 3 is hydrogen; R 4 is hydrogen, fluorine, chlorine, bromine, iodine, amino group, methyl group, ethyl group or methoxy group; A is a single bond; and Cyc is a group of Jl or J2.
  • a pyrimidine compound of Formula (1) wherein Q is oxygen; R 1 is hydrogen; R 2 is hydrogen; G 1 is nitrogen; R 3 is hydrogen; R 4 is hydrogen, chlorine or methyl group; A is a single bond; Cyc is a group of Jl; R 9 is C1-C3 alkyl group optionally substituted with fluorine or chlorine, fluorine, or chlorine; p is 0 or 1; and Y is -S( 0) n - or - CR 11 R 12 - wherein n is 0, 1 or 2, R 11 is fluorine or chlorine, and R 12 is hydrogen, fluorine or chlorine.
  • a pyrimidine compound of Formula (1-vi) is a pyrimidine compound of Formula (1-vi) :
  • R 1 , R 2 , R 3 , R 4 , G 1 and Z are as defined above.
  • the present compound can be prepared by, for example, the following Processes A to G.
  • R 1 , R 2 , R 3 , R 4 , A, Cyc and G 1 are as defined above, and Q' is oxygen or sulfur [hereinafter, referred to as the present compound (1-i)]
  • R 1 , R 2 , R 3 , R 4 and G 1 are as defined above
  • solvent used herein includes, example, water; ether such as 1,4-dioxane, diethyl ether, tetrahydrofuran, and tert-butyl methyl ether; halogenated hydrocarbon such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane, and chlorobenzene ; hydrocarbon such as toluene, benzene, and xylene; nitrile such as acetonitrile; an aprotic polar solvent such as N,N- dimethylformamide, N-methylpyrrolidone (hereinafter, referred to as NMP) , 1 , 3-dimethyl-2-imidazolidinone, and dimethylsulfoxide ; and a mixture thereof.
  • solvent used herein includes, example, water; ether such as 1,4-dioxane, diethyl ether, tetrahydrofuran, and tert-butyl
  • the amount of Compound (3) used herein is generally 1 mol to 2 mol per 1 mol of Compound (2) .
  • the reaction is generally carried out in the presence of a base.
  • the base used herein includes, for example, a nitrogen-containing heterocyclic compound such as pyridine, picoline, 2 , 6-lutidine, 1, 8-diazabicyclo [5.4.0] -undec-7-ene (hereinafter, referred to as DBU) , and 1,5- diazabicyclo [ 4.3.0 ] -non-5-ene ; tertiary amine such as triethylamine and N-ethyldiisopropylamine ; and an inorganic base such as potassium carbonate and sodium hydride.
  • the amount of the base used herein is generally 1 mol or more per 1 mol of Compound (2) .
  • the reaction temperature is generally in the range of
  • reaction time is generally in the range of 0.1 hour to 24 hours.
  • the present compound (1-i) can be isolated by pouring the reaction mixture into water, extracting the organic solvent, and then concentrating the organic layer; or by pouring the reaction mixture into water, and then collecting the resultant solid with a filter; or by collecting the solid generated in the reaction mixture with a filter.
  • the isolated present compound (1-i) can be further purified by, for example, recrystallization and chromatography.
  • the present compound (1-i) can be prepared by reacting a compound of Formula (4) :
  • R 1 , R 2 and G 1 are as defined above [hereinafter, referred to as Compound (5)].
  • the reaction is carried out in the presence or absence of a solvent.
  • the solvent used herein includes, for example, water; ether such as 1,4-dioxane, diethyl ether, tetrahydrofuran, and tert-butyl methyl ether; halogenated hydrocarbon such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane, and chlorobenzene ; hydrocarbon such as toluene, benzene, and xylene; nitrile such as acetonitrile; an aprotic polar solvent such as N,N- dimethylformamide , NMP, 1, 3-dimethyl-2-imidazolidinone, and dimethylsulfoxide; and a mixture thereof.
  • the amount of Compound (5) used herein is generally 1 mol to 2 mol per 1 mol of Compound (4) .
  • the reaction is generally carried out in the presence of a base.
  • the base used herein includes, for example, a nitrogen-containing heterocyclic compound such as pyridine, picoline, 2, 6-lutidine, DBU, and 1 , 5-diazabicyclo [ 4.3.0] - non-5-ene; tertiary amine such as triethylamine and N- ethyldiisopropylamine; and an inorganic base such as potassium carbonate and sodium hydride.
  • the amount of the base used herein is generally 1 mol or more per 1 mol. of Compound (4) .
  • the reaction temperature is generally in the range of -20°C to 100°C.
  • the reaction time is generally in the range of 0.1 hour to 24 hours.
  • the present compound (1-i) can be isolated by pouring the reaction mixture into water, extracting the organic solvent, and then concentrating the organic layer; or by pouring the reaction mixture into water, and then collecting the resultant solid with a filter; or by collecting the solid generated in the reaction mixture with a filter.
  • the isolated present compound (1-i) can be further purified by, for example, recrystallization and chromatography.
  • the present compound (1-i) can be prepared by reacting a compound of Formula (6) :
  • R 1 , R 2 , R 3 , R 4 and G 1 are as defined above [hereinafter, referred to as Compound (6)]
  • the reaction is carried out in the presence or absence of a solvent.
  • the solvent used herein includes, for example, water; ether such as 1,4-dioxane, diethyl ether, tetrahydrofuran, and tert-butyl methyl ether; halogenated hydrocarbon such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane, and chlorobenzene ; hydrocarbon such as toluene, benzene, and xylene; nitrile such as acetonitrile; an aprotic polar solvent such as N,.N- dimethylformamide, NMP, 1, 3-dimethyl-2-imidazolidinone, and dimethylsulfoxide ; and a mixture thereof.
  • the amount of Compound (3) used herein is generally 1 mol to 2 mol per 1 mol of Compound (6) .
  • the reaction is generally carried out in the .presence of a base.
  • the base used herein includes, for example, a nitrogen-containing heterocyclic compound such as pyridine, picoline, 2 , 6-lutidine, DBU, and 1 , 5-diazabicyclo [ .3.0 ] - non-5-ene; tertiary amine such as triethylamine and N- ethyldiisopropylamine ; and an inorganic base such as potassium carbonate and sodium hydride.
  • the amount of the base used herein is generally 1 mol or more per 1 mol of Compound (6) .
  • the reaction temperature is generally in the range of -20°C to 100°C.
  • the reaction time is generally in the range of 0.1 hour to 24 hours.
  • the present compound . (1-i) can be isolated by pouring the reaction mixture into water, extracting the organic solvent, and then concentrating the organic layer; or by pouring the reaction mixture into water, and then collecting the resultant solid with a filter; or by collecting the solid generated in the reaction mixture with a filter.
  • the isolated present compound (1-i) can be further purified by, for example, recrystallization and chromatography.
  • the present compound (1-i) can be prepared by reacting a compound of Formula (7) :
  • R 1 , R 2 , R 3 ,. R 4 , G 1 and Q' are as defined above [hereinafter, referred to as Compound (7)] with a compound of Formula (8) :
  • a and Cyc are as defined above, and L is a leaving group such as chlorine, bromine, iodine, p- toluenesulfonyloxy group and methanesulfonyloxy group [hereinafter, referred to as Compound (8)].
  • the reaction is carried out in the presence or absence of a solvent.
  • the solvent used herein includes, for example, water; ether such as 1,4-dioxane, diethyl ether, tetrahydrofuran, and tert-butyl methyl ether; halogenated hydrocarbon such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane, and chlorobenzene ; hydrocarbon such as toluene, benzene, and xylene; nitrile such as acetonitrile ; an aprotic polar solvent such as N,N- dimethylformamide, NMP, 1, 3-dimethyl-2-imidazolidinone, and dimethylsulfoxide ; and a mixture thereof.
  • the amount of Compound (8) used herein is generally 1 mol to 2 mol per 1 mol of Compound (7) .
  • the reaction is generally carried out in . the presence of a base.
  • the base used herein includes, for example, a nitrogen-containing heterocyclic compound such as pyridine, picoline, 2 , 6-lutidine, DBU, and 1 , 5-diazabicyclo [ 4.3.0 ] - non-5-ene; tertiary amine such as triethylamine and N- ethyldiisopropylamine ; and an inorganic base such, as potassium carbonate and sodium hydride.
  • the amount of the base used herein is generally 1 mol or more per 1 mol of Compound (7) .
  • the reaction temperature is generally in the range of -20°C to 100°C.
  • the reaction time is generally in. the range of 0.1 hour to 24 hours.
  • (1-i) can be isolated by pouring the reaction mixture into water, extracting the organic solvent, and then concentrating the organic layer; or by pouring the reaction mixture into water, and then collecting the resultant solid with a filter; or by collecting the solid generated in the reaction mixture with a filter.
  • the isolated present compound (1-i) can be further purified by, for example, recrystallization and chromatography.
  • R 1 , R 2 , R 3 , R 4 and G 1 are as defined above, and n-1 is 1 or 2 [hereinafter, referred to as the present compound (1-ii)]
  • the reaction is generally carried out in the presence of a solvent.
  • the solvent used herein includes, for example, aliphatic halogenated hydrocarbon such as dichloromethane and chloroform; alcohol such as methanol and ethanol; acetic acid; water; and a mixture thereof.
  • the oxidizing agent used herein includes, for example, hydrogen peroxide solution, sodium periodate and m- chloroperbenzoic acid.
  • the amount of oxidizing agent used herein is generally 1 mol to 1.2 mol per 1 mol of Compound (1-iii) .
  • the amount of oxidizing agent used herein is generally 2 mol to 3 mol per 1 mol of Compound (1-iii) .
  • the reaction temperature is generally in the range of -20°C to 80°C.
  • the reaction time is generally in the range W 201
  • the present compound (1-ii) can be isolated by post treatments such as extracting the reaction mixture with an organic solvent, optionally washing the organic layer with an aqueous solution of a reducing agent (e.g. sodium sulfite and sodium thiosulfate) or a base (e.g. sodium bicarbonate), and then drying and concentrating the resultant mixture.
  • a reducing agent e.g. sodium sulfite and sodium thiosulfate
  • a base e.g. sodium bicarbonate
  • R 1 , R 2 , R 3 , R 4 , Z and G 1 are as defined above [hereinafter, referred to as the present compound (l-vi)] or a compound of Formula (1-vii) :
  • R 1 , R 2 , R 3 , R 4 , Z and G 1 are as defined above [hereinafter, referred to as the present compound (1-vii)] can be prepared by reacting a compound of Formula (1-viii):
  • R 1 , R 2 , R 3 , R 4 and G 1 are as defined above [hereinafter, referred to as the present compound (1-viii)] with a halogenating agent.
  • the halogenating agent used herein is a fluorinating agent, and the fluorinating agent includes, for example, (diethylamino) sulfur trifluoride (hereinafter, referred to as DAST) , bis ( 2-methoxyethyl ) aminosulfur trifluoride and 2 , 2-difluoro-1 , 3-dimethyl-imidazolidine .
  • DAST diethylamino sulfur trifluoride
  • DAST bis ( 2-methoxyethyl ) aminosulfur trifluoride and 2 , 2-difluoro-1 , 3-dimethyl-imidazolidine .
  • the reaction is generally carried out in the presence of a solvent.
  • the solvent used herein includes, for example, 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, NMP, 1, 3-dimethyl-2-imidazolidinone, and dimethylsulfoxide; and a mixture thereof.
  • the amount of the fluorinating agent used herein is generally 1 mol to 4 mol per 1 mol of the present compound (1-viii) .
  • the reaction temperature is generally in the range of -20°C to 100°C.
  • the reaction time is generally in the range of 0.1 hour to 24 hours.
  • the present compounds (1-vi) and (1-vii) can. be isolated by pouring the reaction mixture into water and then extracting the organic solvent, or by collecting the resultant precipitate with a filter.
  • the isolated present compounds (1-vi) and (1-vii) can be further purified by, for example, recrystallization and chromatography .
  • the halogenating agent used herein is a chlorinating agent, and the chlorinating agent includes, for example, tungsten hexachloride .
  • the reaction is generally carried out in the presence of a solvent.
  • the solvent used herein includes, for example, 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, NMP, 1, 3-dimethyl-2-imidazolidinone, and dimethylsulfoxide ; and a mixture thereof.
  • the amount of the chlorinating agent used herein is generally 1 mol to 4 mol per 1 mol of the present compound ( 1-viii ) .
  • the reaction temperature is generally in the range of -20°C to 100°C.
  • the reaction time is generally in the range of 0.1 hour to 24 hours.
  • the present compounds (1-vi) and (1-vii) can be isolated by pouring the reaction mixture into water and then extracting the organic solvent, or by collecting the resultant precipitate with a filter.
  • the isolated present compounds (1-vi) and (1-vii) can be further purified by, for example, recrystallization and chromatography.
  • the halogenating agent used herein is a brominating agent, and the brominating agent includes, for example, bromine, boron tribromide, boron pentabromide , and a mixture thereof.
  • Compound (2) can be prepared by reacting a compound of Formula ( 9 ) :
  • the reaction is carried out in the presence or absence of a solvent.
  • the solvent used herein 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, NMP, 1, 3-dimethyl-2-imidazolidinone, and dimethylsulfoxide; and a mixture thereof.
  • the amount of Compound (5) used herein is generally 1 mol to 2 mol per 1 mol of Compound (9) .
  • the reaction is generally carried out in the presence of a base.
  • the base used herein includes, for example, a nitrogen-containing heterocyclic compound such as pyridine, picoline, 2, 6-lutidine, DBU, and 1 , 5-diazabicyclo [ 4.3.0 ] - ⁇ -5-ene; tertiary amine such as triethylamine and N- ethyldiisopropylamine ; and an inorganic base such as potassium carbonate and sodium hydride.
  • the amount of the base used herein is generally 1 mol or more per 1 mol of Compound (9) .
  • the reaction temperature is generally in the range of -20°C to 100°C.
  • the reaction time is generally in the range of 0.1 hour to 24 hours.
  • Compound (2) can be isolated by pouring the reaction mixture into water, extracting the organic solvent, and then concentrating the organic layer; or by pouring the reaction mixture into water, and then collecting the resultant solid with a filter; or by collecting the solid generated in the reaction mixture with a filter.
  • the isolated Compound (2) can be further purified by, for example, recrystallization and chromatography.
  • R 1"1 is C1-C3 chain hydrocarbon group optionally substituted with one or more halogens, or hydrogen; and and R 4 are as defined above [hereinafter, referred to
  • R 29 is C1-C6 alkyl group optionally substituted with one or more halogens, and R 1"1 are as defined above [hereinafter, referred to as Compound (11)].
  • the reaction is carried out in the presence or absence of a solvent.
  • the solvent used herein 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, NMP, 1 , 3-dimethyl-2-imidazolidinone , and dimethylsulfoxide; and a mixture thereof.
  • the amount of Compound (11) used herein is generally 1 mol to 2 mol per 1 mol of Compound (10) .
  • the reaction temperature is generally in the range of -20°C to 100°C.
  • the reaction time is generally in the range of 0.1 hour to 24 hours.
  • Compound (2-i) can be isolated by pouring the reaction mixture into water, extracting the organic solvent, and then concentrating the organic layer.
  • the isolated Compound (2-i) can be further purified by, for example, chromatography and distillation.
  • Compound (10) can be prepared by reacting Compound (9) with hydrazine.
  • the reaction is carried out in the presence or absence of a solvent.
  • the solvent used herein 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, NMP, 1 , 3-dimethyl-2-imidazolidinone , and dimethylsulfoxide ; and a mixture thereof.
  • the hydrazine used herein includes, for example, hydrazine and hydrazine hydrate.
  • the amount of hydrazine used herein is generally 1 mol to 10 mol per 1 mol of Compound (9) .
  • the reaction is generally carried out in the presence of a base.
  • the base used herein includes, for example, a nitrogen-containing heterocyclic compound such as pyridine, picoline, 2 , 6-lutidine, DBU, and 1 , 5-diazabicyclo [ .3.0] - non-5-ene; tertiary amine such as triethylamine and N- ethyldiisopropylamine; and an inorganic base such as potassium carbonate and sodium hydride.
  • the amount of the base used herein is generally 1 mol or more per 1 mol of Compound ( 9 ) .
  • the reaction temperature is generally in the range of 0°C to 100°C.
  • the reaction time is generally in the range of 0.1 hour to 24 hours.
  • Compound (10) can be isolated by pouring the reaction mixture into water, extracting the organic solvent, and then concentrating the organic layer; or by pouring the reaction mixture into water, and then collecting the resultant solid with a filter; or by collecting the solid generated in the reaction mixture with a filter.
  • the isolated Compound (10) can be further purified by, for example, recrystallization and chromatography.
  • Compound (4) can be prepared by reacting Compound (9) and Compound (3) .
  • the reaction is carried out in the presence or absence of a solvent.
  • the solvent used herein includes, for example, water; ethers such as 1,4-dioxane, diethyl ether, tetrahydrof.uran, 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 dimethylsulfoxide; and a mixture thereof.
  • the amount of Compound (3) used herein is generally 1 mol to 2 mol per 1 mol of Compound (9) .
  • the reaction is generally carried out in the presence of a base.
  • the base used herein includes, for example, a nitrogen-containing heterocyclic compound such as pyridine, picoline, 2 , 6-lutidine, DBU, and 1 , 5-diazabicyclo [ 4.3.0 ] - non-5-ene; tertiary amine such as triethylamine and N- ethyldiisopropylamine; and an inorganic base such as potassium carbonate and sodium hydride.
  • the amount of the base used herein is generally 1 mol or more per 1 mol of Compound (9) .
  • the reaction temperature is generally in the range of 0°C to 100°C.
  • the reaction time is generally in the range of 0.1 hour to 24 hours *
  • Compound (4) can be isolated by pouring the reaction mixture into water and then extracting the organic solvent.
  • the isolated Compound (4) can be further purified by, for example, chromatography [0069]
  • Compound (6) can be prepared by reacting Compound (9) with Compound (5) .
  • the reaction is carried out in the presence or absence of a solvent.
  • the solvent used herein includes, for example, water; ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran, and tert-butyl methyl ether; halogenated hydrocarbons .
  • the amount of Compound (5) used herein is generally 2 mol to 3 mol per 1 mol of Compound (9) .
  • the reaction is generally carried out in the presence of a base.
  • the base used herein includes, for example, a nitrogen-containing heterocyclic compound such as pyridine, picoline, 2, 6-lutidine, DBU, and 1 , 5-diazabicyclo [ 4.3.0 ] - non-5-ene; tertiary amine such as triethylamine and N- ethyldiisopropylamine; and an inorganic base such as potassium carbonate and sodium hydride.
  • the amount of the base used herein is generally 2 mol or more per 1 mol of Compound (9) .
  • the reaction temperature is generally in the range of 0°C to 100°C.
  • the reaction time is generally in the range of 0.1 hour to 24 hours.
  • Compound (6) can be isolated by pouring the reaction mixture into water, extracting the organic solvent, and then concentrating the organic layer; or by pouring the reaction mixture into water, and then collecting the resultant solid with a filter; or by collecting the solid generated in the reaction mixture with a filter.
  • the isolated Compound (.6) can be further purified by, for example, recrystallization and chromatography.
  • R 1 , R 2 , R 3 , R 4 and G 1 are as defined above.
  • the reaction is carried out in the presence of water as well as a base or an acid.
  • a solvent is optionally used herein, and the solvent includes, for example, ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran, tert-butyl methyl ether, and diglyme; hydrocarbons such as toluene, benzene, and xylene; and nitriles such as acetonitrile .
  • the base used herein includes, for example, an inorganic base such as potassium carbonate , sodium hydroxide, potassium hydroxide, and sodium hydride; a nitrogen-containing heterocyclic compound such as pyridine, picoline, 2 , 6-lutidine, DBU, and 1 , 5-diazabicyclo [ 4.3.0 ] - non-5-ene; and tertiary amine such as triethylamine and N- ethyldiisopropylamine .
  • the amount of the base used herein is generally 0.1 mol to 4 mol per 1 mol of Compound (6) .
  • the acid used herein includes, for example, an inorganic acid such as hydrochloric acid, hydrobromic acid, and sulfuric acid; and an organic acid such as acetic acid and p-toluenesulfonic acid.
  • an inorganic acid such as hydrochloric acid, hydrobromic acid, and sulfuric acid
  • an organic acid such as acetic acid and p-toluenesulfonic acid.
  • the reaction temperature is generally in the range of 20°C to 120°C.
  • the reaction time is generally in the range of 0.1 hour to 24 hours.
  • Compound (7-i) can be isolated by pouring the reaction mixture into water, extracting the organic solvent, and then concentrating the organic layer; or by pouring the reaction mixture into water, and ⁇ then collecting the resultant solid with a filter; or by collecting the solid generated in the reaction mixture with a filter.
  • the isolated Compound (7- i) can be further purified by, for example, recrystallization and chromatography.
  • the reaction is carried out in the presence or absence of a solvent.
  • the solvent used herein includes, for example, ethers such as 1,4-dioxane, diethyl ether, 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; pyridine derivatives such as pyridine, picoline, and lutidine; and a mixture thereof.
  • the sulfidizing agent used herein includes, for example, phosphorus pentasulfide and Lawesson's reagent [i.e. 2 , 4-bis- ( 4 -methoxyphenyl ) -1, 3-dithia-2, 4- diphosphetane 2 , 4-disulfide] .
  • the amount of the sulfidizing agent used herein is generally 1 mol or more per 1 mol of Compound (7-i) .
  • the reaction temperature is generally in the range of
  • reaction time is generally in the range of 1 hour to 24 hours.
  • Compound (7-ii) can be. isolated by pouring the reaction mixture into water, extracting the organic solvent, and then concentrating the organic layer; or by pouring the reaction mixture into water, and then collecting the resultant solid with a filter; or by collecting the solid generated in the reaction mixture with a filter.
  • the isolated Compound (7- ii) can be further purified by, for example, recrystallization and chromatography.
  • R 1 and R 3 are hydrogen; Q is oxygen; and Cyc, A, and R 2 are any one of the combinations listed in Tables to 6.
  • R 1 and R 3 are hydrogen; Q is oxygen; and Cyc, A, and R 2 are any one of the combinations listed in Tables to 6.
  • R 1 and R 3 are hydrogen; Q is oxygen; and Cyc, A, G 1 and R 2 are any one of the combinations listed in Tables 1 to 6.
  • R 1 and R 3 are hydrogen; Q is oxygen; and Cyc, A, G 1 and R 2 are any one of the combinations listed in Tables 1 to 6.
  • R 1 and R 3 are hydrogen; Q is oxygen; and Cyc, A, and R are any one of the combinations listed in Tables to 6.
  • R 1 and R 3 are hydrogen; Q is oxygen; and Cyc, A, G 1 and R are any one of the combinations listed in Tables 1 to 6.
  • a compound of Formula (G) W 201
  • R 1 and R 3 are hydrogen; Q is oxygen; and Cyc, A, and R 2 are any one of the combinations listed in Tables to 6.
  • R 1 and R 3 are hydrogen; Q is sulfur; and Cyc, A, G 1 and R 2 are any one of the combinations listed in Tables 1 to 6.
  • R 1 and R 3 are hydrogen; Q is sulfur; and Cyc, A, ... G 1 and R 2 are any one of the combinations listed in Tables 1 to 6. [0088] .
  • R 1 and R 3 are hydrogen; Q is sulfur;, and Cyc, A, G 1 and R 2 are any one of the combinations listed in Tables 1 to 6.
  • the present compounds are effective against pests such as harmful arthropods (e.g. harmful insects and mites), nematodes, and mollusks.
  • pests such as harmful arthropods (e.g. harmful insects and mites), nematodes, and mollusks.
  • harmful arthropods e.g. harmful insects and mites
  • nematodes e.g. nematodes
  • mollusks mollusks
  • 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) , Taiwan 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) , spirea 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 a
  • Lepidoptera Pyralid moths (Pyralidae) such as rice stem borer (Chilo suppressalis) , yellow stem 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) , rice armyworm (Pseudaletia separata) , . cabbage armyworm ⁇ Mamestra brassicae) , black cutworm (Agrotis ipsilon) , beet semi- looper (Plusia nigrisigna) , Thoricoplusia spp.
  • Noctuidae such as common cutworm ⁇ Spodoptera litura) , beet armyworm ⁇ Spodoptera exigua) , rice armyworm (Pseudaletia separata) , . cabbage armyworm ⁇ Mamestra brassicae) , black cutworm (Agrotis ipsilon) , beet semi
  • Carposinidae such as peach fruit moth ⁇ Carposina niponensis) ; lyonetiid moths ⁇ Lyonetiidae) such as Lyonetia spp.; tussock moths ⁇ Lymantriidae) such as Lymantria spp.
  • yponomeutid moths ⁇ Yponomeutidae such as diainondback moths ⁇ Plutella xylostella)
  • gelechiid moths such as pink bollworm (Pectinophora gossypiella) and potato tubeworm ⁇ Phthorimaea operculella)
  • tiger moths ⁇ Arctiidae such as fall webworm ⁇ Hyphantria cunea)
  • tineid moths (Tineidae) such as casemaking clothes moth ⁇ Tinea translucens) and webbing clothes moth (Tineola bisselliella) ; and the like.
  • Thrips ⁇ Thripidae such as yellow citrus thrip ( Frankliniella occidentalis) , melon thrip ⁇ Thrips peri) , yellow tea thrip ⁇ Scirtothrips dorsalis) , onion thrip ⁇ Thrips tabaci) , flower thrip ⁇ Frankliniella intonsa) , and the like.
  • Diptera House mosquitos (Culex) such as common house mosquito ⁇ Culex pipiens pallens) , small house mosquito
  • Anopheles spp. such as Chinese anopheles
  • Chroma tomyia horticola Chroma tomyia horticola
  • frit flies Chloropidae
  • rice stem maggot Chlorops oryzae
  • Tephritidae such as melon fly (Dacus cucurbitae) and Mediterranean fruit fly ⁇ Ceratitis capitata) ; Drosophilidae; humpbacked flies (Phoridae) such as humpbacked flies ⁇ Megaselia spiracularis) ; sand 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
  • beetles [Bostrichidae) ; spider beetles ⁇ Ptinidae) ; longhorn beetles ⁇ Cerambycidae) such as . white-spotted longicorn beetle ⁇ Anoplophora malasiaca) ; Agriotes spp.; rove beetles (Paederus fuscipes) ; and the like.
  • Orthoptera Asiatic locust (Locusta migratoria) , African mole cricket ⁇ Gryllotalpa africana) , rice grasshopper ⁇ Oxya yezoensis) , rice grasshopper ⁇ Oxya japonica) , cricket [Gry11idae) , and the like.
  • Shiphonaptera Cat flea ⁇ Ctenocephalides felis) , dog flea ⁇ Ctenocephalides canis) , human flea ⁇ Pulex irritans) , oriental rat flea ⁇ Xenopsylla cheopis) , and the like.
  • Anoplura Human body louse ⁇ Pediculus humanus corporis), crab louse ⁇ Phthirus pubis), short-nosed cattle louse ⁇ Haematopinus eurysternus) , sheep louse ⁇ Dalmalinia ovis) , hog louse ⁇ Haematopinus suis), and the like.
  • Hymenoptera Ants ⁇ Formicidae) such as pharaoh ant
  • Termitidae Japanese subterranean termite ⁇ Reticulitermes speratus) , Formosan subterranean termite ⁇ Coptotermes formosanus), western drywood termite ( Incisitermes minor), tropical drywood termite
  • 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.
  • eriophyidmites ⁇ Eriophyidae such as pink citrus rust mite ⁇ Aculops pelekassi) , pink citrus rust mite ⁇ Phyllocoptruta citri), tomato rust mite ⁇ Aculops lycopersici) , purple tea mite ⁇ Calacarus carinatus) , tea rust mite (Acaphylla theavagrans) , Japanese pear rust mite (Eriophyes chibaensis) , and apple rust .
  • mite (Aculus pointedendali) ; tarosonemid mites ⁇ Tarsonemidae) such as broad mite ⁇ Polyphagotarsonemus latus) ; false spider mites ⁇ Tenuipalpidae) such as flat mite ⁇ Brevipalpus phoenicis) ; peacock mites ⁇ Tuckerellidae) ; ticks ⁇ Ixodidae) such, as New Zealand cattle tick ⁇ Haemaphysalis .
  • acarid mites ⁇ Acaridae) such as mold mite ⁇ Tyrophagus putrescentiae) and acarid mite ⁇ Tyrophagus similis)
  • house dust mites Pyroglyphidae
  • American house dust mite ⁇ Dermatophagoides farinae and European house dust mite ⁇ Dermatophagoides ptrenyssnus
  • ⁇ Cheyletidae such as cheyletid mite ⁇ Cheyletus eruditus) , Cheyletus malaccensis and Cheyletus moorei; parasitoid mites ⁇ Dermanyssidae) such as tropical rat mite ⁇ Ornithonyssus bacoti) , northern fowl mite ⁇ Ornithonyssus sylviarum) , and poultry redmite ⁇ Dermanyssus gallinae) ; chiggers ⁇ Trombiculidae) such as Le otromj idium akamushi; spiders ⁇ Araneae) such as Japanese foliage spider ⁇ Chiracanthium japonicum) and redback spider ⁇ Latrodectus hasseltii) ; and the like.
  • parasitoid mites ⁇ Dermanyssidae such as tropical rat
  • Chilopoda House centipede ⁇ Thereuonema hilgendorfi) , Vietnam giant centipede (Scolopendra subspinipes) , and the like.
  • Diplopoda Garden millipede ⁇ Oxidus gracilis) , red millipede (Nedyopus tambanus) , and the like.
  • Isopoda Common pill bug (Armadillidium vulgare) and the like.
  • Gastropoda Tree slug (Limax marginatus) , yellow slug (Limax flavus) , and the like.
  • Nematoda Rice white-tip nematode (Aphelenchoides besseyi) , strawberry bud nematode (Nothotylenchus acris) , cotton root-knot nematode (Meloidogyne incognita) , northern root-knot nematode (Meloidogyne hapla) , tropical root-knot nematodes (Meloidogyne javanica) , soybean cyst nematode (Heterodera glycines) , potato cyst nematode (Globodera rostochiensis) , coffee root-lesion nematode (Pratylenchus coffeae) , roOt ⁇ iesion nematode (Pratylenchus neglectus) , and the like.
  • the pesticidal agent of the present invention comprises the present compound and an inert carrier.
  • the pesticidal agent of the present invention is generally formulated into, for example, an emulsion, an oil solution, a powder, a granule, a wettable powder, a flowable formulation, a microcapsule agent, an aerosol, a smoking agent, a toxic bait, or a resin formulation by mixing the present compound and an inert carrier (e.g. solid carrier, liquid carrier, and gas carrier) , and, if necessary, adding a surfactant or other formulation additives.
  • an inert carrier e.g. solid carrier, liquid carrier, and gas carrier
  • the pesticidal agent of the present invention generally contains the present compound in an amount of 0.01 wt% to 95 wt%.
  • the solid carrier used herein includes, for example, fine powders and granular materials made from, for example, clays (e.g.. kaolin clay, diatomaceous earth, bentonite, Fubasami clay, and acid clay) / synthetic hydrated silicon oxide; talc; ceramic; other inorganic minerals (e.g. sericite, quartz, sulfur, activated charcoal, calcium carbonate, and hydrated silica) ; and chemical fertilizers (e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, and ammonium chloride) .
  • clays e.g... kaolin clay, diatomaceous earth, bentonite, Fubasami clay, and acid clay
  • synthetic hydrated silicon oxide talc
  • ceramic other inorganic minerals
  • other inorganic minerals e.g. sericite, quartz, sulfur, activated charcoal, calcium carbonate, and hydrated silica
  • chemical fertilizers e.g. ammonium
  • the liquid carrier used herein includes, for example, water; alcohols (e.g. methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, and phenoxy ethanol); ketones (e.g. acetone, methyl ethyl ketone, and cyclohexanone ) ; aromatic hydrocarbons (e.g. toluene, xylene, ethylbenzene, dodecylbenzene , phenylxylylethane , and methylnaphthalene) ; aliphatic hydrocarbons (e.g.
  • esters e.g.. ethyl acetate, butyl acetate, isopropyl myristate, ethyl oleate, diisopropyl adipate, diisobutyl adipate, and. propylene glycol monomethyl ether acetate
  • nitriles e.g. acetonitrile and isobutyronitrile
  • ethers e.g.
  • acid amides e.g. ⁇ ⁇ : ⁇ N, N-dimethylformamide and N,N- dimethylacetamide
  • halogenated hydrocarbons e.g. dichloromethan
  • the gas carrier used herein includes, for example, fluorocarbon, butane gas, LPG (liquefied petroleum gas), dimethyl ether and carbon dioxide gas.
  • the surfactant used herein includes,- for example, a non-ionic surfactant such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, and polyethylene glycol fatty acid ester; and an anionic surfactant such as alkyl sulfonate, alkylbenzene sulfonate, and alkyl sulfate. - [0111]
  • the other formulation additives used herein include, fixing agents, dispersing agents, colorants, stabilizers, and the like; and more specifically, casein, gelatin, saccharides (e.g. starch, gum arabic, cellulose derivatives, and alginic acid), lignin derivatives, bentonite, synthetic water-soluble polymers (e.g.
  • polyvinyl alcohols polyvinyl pyrrolidones, and polyacrylic acids
  • PAP acidic isopropyl phosphate
  • BHT 2 , 6-di-tert-butyl- -methylphenol
  • BHA a mixture of 2-tert-butyl-4 -methoxyphenol and 3-tert-butyl-4 - methoxyphenol
  • the method for controlling pests in the present invention is performed by applying an effective amount of the present compound to pests directly and/or habitats of pests (e.g. plant body, soil, indoor, and animal body).
  • pests e.g. plant body, soil, indoor, and animal body.
  • the present compound is generally used in the form of a pesticidal agent of the present invention.
  • the habitats of pests include, for example, paddy fields, dry paddy fields, fields, tea fields, orchards, non-crop lands, houses, seedling raising trays, seedling raising boxes, seedling raising soils, seedling raising mats, and water culture solutions in water culture farms.
  • the application amount thereof is 1 g to 10, 000 g of the present compound per 10, 000 m 2 .
  • the pesticidal agent of the present invention is formulated into, for example, emulsions, wettable powders, and flowable formulations, the pesticidal agent is generally diluted with water so that the active ingredient concentration thereof can be 0.01 ppm to 10,000 ppm.
  • the pesticidal agent is formulated into, for example, granules and powders, the pesticidal agent is generally used without dilution.
  • formulations and water dilutions thereof may be directly sprayed to pests or plants (e.g. crops which need to be protected from pests), or may be applied to a soil of a cultivated land in order to control pests which inhabit the soil.
  • the pesticidal agent of the present invention can also be used in the form of a resin preparation which may be, for example, processed into a sheet or a string, and then wound around crops, or put around crops, or laid on the soil surface near the root of crops.
  • the pesticidal agent of the present invention can be used for controlling pests which live in a house. When it is used at a plain surface, the application amount thereof is generally 0.01 mg to 1, 000 mg of the present compound per 1 m 2 of the treatment area; and when it is used in an open space, the application amount thereof is generally 0.01 mg to 500 mg of the present compound per 1 m 3 of the treatment space.
  • the pesticidal agent of the present invention is formulated into, for example, emulsions, wettable powders, and flowable formulations, the pesticidal agent is generally diluted with water so that the active ingredient concentration thereof can be 0.1 ppm to 1,000 ppm.
  • the pesticidal agent is formulated into, for example, oil solution, aerosol, smoking agent and toxic bait, the pesticidal agent is generally used without dilution.
  • the pesticidal agent of the present invention can be used in farmlands where the following "crops" are cultivated.
  • Agricultural crops Corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, sarrazin, sugar beet, rapeseed, sunflower, sugar cane, tobacco, and the like.
  • Vegetables Solanaceae vegetables (e.g. eggplant, tomato, green . pepper, hot pepper, and potato) , Cucurbitaceae vegetables (e.g. cucumber, pumpkin, zucchini, watermelon, and melon), Cruciferae vegetables (e.g. Japanese radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, brown mustard, broccoli, and cauliflower) , Compositae vegetables (e.g. burdock, garland chrysanthemum, artichoke, and lettuce), Liliaceae vegetables (e.g. Welsh onion, onion, garlic, and asparagus) , Umbelliferae vegetables (e.g.
  • carrot, parsley, celery, and parsnip Chenopodiaceae vegetables (e.g. spinach and Swiss chard), Labiatae vegetables (e.g. Japanese basil, mint, and basil), strawberry, sweat potato, yam, aroid, and the like.
  • Chenopodiaceae vegetables e.g. spinach and Swiss chard
  • Labiatae vegetables e.g. Japanese basil, mint, and basil
  • strawberry sweat potato, yam, aroid, and the like.
  • Fruit trees Pomaceous fruits (e.g. apple, common pear, Japanese pear, Chinese quince, and quince) , stone fleshy fruits (e.g. peach, plum, nectarine, Japanese plum, cherry, apricot, and prune), citrus plants (e.g. Satsuma mandarin, orange, lemon, lime, and grapefruit), nuts (e.g. chestnut, walnut, hazel nut, almond, pistachio, cashew nut, and macadamia nut), berry fruits (e.g. blueberry, cranberry, blackberry, and raspberry) , grape, persimmon, olive, loquat, 9.7 banana, coffee, date, coconut, oil palm, and the like.
  • Pomaceous fruits e.g. apple, common pear, Japanese pear, Chinese quince, and quince
  • stone fleshy fruits e.g. peach, plum, nectarine, Japanese plum, cherry, apricot, and prune
  • citrus plants e.
  • Trees other than fruit trees Tea, mulberry, flowering trees and shrubs (e.g. Rhododendron indicum, Camellia japonica, Hydrangea, Camellia sasanqua, Illicium anisatum, Prunus subg. Cerasus, - Liriodendron tulipifera, Lagerstroemia indica, and Osmanthus fragrans var. aurantiacus ) , street trees (e.g.
  • 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, and the like.
  • Lawn Zoysia (e.g. Japanese lawn grass and mascarene grass), Bermuda grass (e.g. Cynodon dactylon) , bent grass (e.g. creeping bent grass, Agrostis stolonifera, and Agrostis tenuis), bluegrass (e.g. Kentucky bluegrass and rough bluegrass), fescue (e.g. tall fescue, chewing fescue, and creeping fescue), ryegrass (e.g. darnel and perennial. ryegrass), cocksfoot, timothy grass, and the like.
  • Zoysia e.g. Japanese lawn grass and mascarene grass
  • Bermuda grass e.g. Cynodon dactylon
  • bent grass e.g. creeping bent grass, Agrostis stolonifera, and Agrostis tenuis
  • bluegrass e.g. Kentucky bluegrass and rough bluegrass
  • fescue e.g.
  • the "crops” also include recombinant crops.
  • the pesticidal agent of the present invention can be mixed or used together with other insecticides, acaricides, nematicides, fungicides, plant growth regulators, herbicides and/or synergists.
  • insecticides acaricides, nematicides, fungicides, plant growth regulators, herbicides and/or synergists.
  • examples of the active ingredients of the above-mentioned insecticides, acaricides, nematicides, fungicides, plant growth regulators, herbicides and synergists are illustrated.
  • Methidathion (DMTP ) , Mevinphos, Monocrotophos , Naled (BRP) , Omethoate, Oxydemeton-methyl , Parathion, Parathion-methyl , Phenthoate (PAP), Phorate, Phosalone, Phosmet (PMP), Phosphamidon, Phoxim, Pirimiphos-methyl , Profenofos, Propetamphos, Prothiofos, Pyraclorfos, Pyridafenthion, Quinalphos, Sulfotep, Tebupirimfos , Temephos, Terbufos, Tetrachlorvinphos, Thiometon, Triazophos, Trichlorphon (DEP) , Vamidothion, Aluminium phosphide, Butathiofos, Dichlorodiisopropyl ether, Dichlofenthion (ECP) , Formothion, Hydrogen phosphide, Oxyde
  • Bistrifluron Chlorfluazuron, Diflubenzuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Noviflumuron, Teflubenzuron, Triflumuron, and Fluazuron.
  • Acetoprole, Ethiprole, Fipronil, Vaniliprole, Pyriprole, and Pyrafluprole are examples of the compounds listed above.
  • Chromafenozide Halofenozide , Methoxyfenozide , and Tebufenozide .
  • R is chlorine atom, bromine atom or trifluoromethyl group
  • R 200 is chlorine atom, bromine atom or methyl group
  • R 300 is chlorine atom, bromine atom or cyano group
  • R is chlorine atom, bromine atom or iodine atom, Metoxadiazone, Sulfluramid, Arsenic acid, Benclothiaz, Calcium cyanamide, Calcium polysulfide, Metarn-ammonium, Metam-sodium, Potassium oleate, Sulfur, and Tralopyril.
  • Methyl bromide, 1 3-Dichloropropene , DCIP, Fosthiazate, Levamisol, Methyisothiocyanate, Morantel tartarate, and Im cyafos .
  • sterol biosynthesis-inhibiting compounds such as Azaconazole, Bitertanol, Bromuconazole , Cyproconazole , Difenoconazole, Diniconazole-M, Epoxiconazole, Fenarimol, Fenbuconazole, Flusilazole, Fluquinconazole , Flutriafol, Hexaconazole, Imazalil, Imibenconazole , Ipconazole, Metconazole, Myclobutanil , Nuarimol, Oxpoconazole , Pefurazoate, Penconazole, Prochloraz, Propiconazole , Prothioconazole, Pyrifenox, Simeconazole , Tebuconazole , Tetraconazole, Triadimefon, Triadimenol, Triflumizole , Trifolin, Txiticonazole, Aldimorph, Dodemorph,
  • cytostatic compounds such as Benomyl,. Carbendezim, Fuberidazole, Thiabendazole, Thiphanate, thiophanate-methyl , Diethofencarb, Zoxamide, Pencycuron, and Fluopicolide;
  • signal inhibiting compounds such as Chlozolinate, Iprodione, Procymidone, Vinclozolin, Quinoxyfen,
  • amino acid biosynthesis-inhibiting compounds such as cyprodinil, pyrimethanil , and Mepanipyrim;
  • nucleic acid biosynthesis-inhibiting compounds such as Metalaxyl, Benalaxyl, and Oxolinic acid;
  • lipid/membrane synthesis-inhibiting compounds such as Isoprothiolane, Iprobenfos, Tolclofos-methyl , Prothiocarb, Dimethomorph, Benthiavalicarb-isopropyl, . Iprovalicarb, and Mandipropamid;
  • melanin biosynthesis-inhibiting compounds such as Diclocymet, Carpropamid, Fenoxanil, Fthalide, Tricyclazole , and Pyroquilon;
  • strobilurin compounds such as Azoxystrobin, Dimoxystrobin, Enestrobin, Fluoxastrobin, Kresoxim-methyl , Metominostrobin, Orysastrobin, Picoxystrobin,
  • anilide compounds such as Carboxin, Oxycarboxin,
  • Mepronil Flutoranil, Furametopyr, Thifluzamide, Boscalid, Penthiopyrad, Fluopyram, Bixafen, Isopyrazam, Penflufen, Sedaxan, and Fluxapyrox.ad;
  • resistance induced compounds such as Acibenzolar-S- methyl, Probenazole, Tiadinil, and Isotianil
  • glucan synthesis-inhibiting compounds such as Validamycin A and Polyoxin B
  • protein biosynthesis-inhibiting compounds such as Blastcidin-S , Kasugamycin, and Streptomycin;
  • Fluometuron Isouron, Tebuthiuron, Methabenzthiazuron, Cumyluron, Daimuron, and Methyl-daimuron.
  • Atrazine Ametoryn, Cyanazine, Simazine, Propazine, Simetryn, Dimethametryn, Prometryn, Metribuzin, Triaziflam, W
  • Amiprofos-methyl Butamifos, Bensulide, Piperophos, Anilofos, Glyphosate, Glufosinate, Glufosinate-P, and Bialaphos.
  • Clodinafop-propargyl Cyhalofop-butyl , Diclofop-methyl , Fenoxaprop-ethyl , Fluazifop-butyl, Haloxyfop-methyl ,
  • Imazapyr Imazaquin
  • Imazethapyr Imazethapyr
  • a compound of Formula (1) A compound of Formula (1) :
  • Gyc-A-Q group, R 1 , R 2 , R 3 , R 4 and G 1 are defined in Tables 7 to 15.

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Abstract

L'invention concerne un composé de pyrimidine de formule (1) : (1) dans laquelle R1 représente un groupe hydrocarboné à chaîne en C1-C3, éventuellement substitué par un ou plusieurs halogènes, etc. ; R2 représente un groupe hydrocarboné à chaîne en C1-C3, éventuellement substitué par un ou plusieurs halogènes, etc. ; G1 représente azote ou -CR5=, etc.; R3 représente un groupe hydrocarboné à chaîne en C1-C3, éventuellement substitué par un ou plusieurs halogènes, etc. ; R4 représente un groupe hydrocarboné à chaîne en C1-C6, éventuellement substitué par un ou plusieurs halogènes, etc. ; Q représente oxygène, etc., Cyc représente un groupe cycloalkyle en C3-C8, etc. ; et A représente une simple liaison, etc., ayant une excellente activité de lutte contre les organismes nuisibles.
PCT/JP2011/074232 2010-10-15 2011-10-14 Composés de pyrimidine et leur utilisation en tant que pesticides WO2012050237A1 (fr)

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