US 12,478,067 B2
Heterocyclic compound and harmful arthropod pest control composition containing same
Takeshi Tsuruda, Takarazuka (JP); Yoshihiko Nokura, Takarazuka (JP); and Yasumasa Saito, Takarazuka (JP)
Assigned to SUMITOMO CHEMICAL COMPANY, LIMITED, Chuo-ku (JP)
Appl. No. 17/598,744
Filed by SUMITOMO CHEMICAL COMPANY, LIMITED, Chuo-ku (JP)
PCT Filed Mar. 27, 2020, PCT No. PCT/JP2020/014004
§ 371(c)(1), (2) Date Sep. 27, 2021,
PCT Pub. No. WO2020/203763, PCT Pub. Date Oct. 8, 2020.
Claims priority of application No. 2019-066002 (JP), filed on Mar. 29, 2019; and application No. 2019-235932 (JP), filed on Dec. 26, 2019.
Prior Publication US 2022/0217979 A1, Jul. 14, 2022
Int. Cl. A01N 43/90 (2006.01); A01N 43/54 (2006.01); A01P 7/00 (2006.01); C07D 401/04 (2006.01); C07D 471/04 (2006.01); C07D 519/00 (2006.01)
CPC A01N 43/90 (2013.01) [A01N 43/54 (2013.01); A01P 7/00 (2021.08); C07D 401/04 (2013.01); C07D 471/04 (2013.01); C07D 519/00 (2013.01)] 17 Claims
 
1. A compound represented by formula (I):

OG Complex Work Unit Chemistry
wherein
Q represents a group represented by formula Q2,

OG Complex Work Unit Chemistry
Z represents an oxygen atom or a sulfur atom,
A1 represents CR4a, and A2 represents a nitrogen atom,
a combination of B1, B2, B3 and B4 represents,
a combination in which B1 represents a nitrogen atom or CR6a, B2 represents CR1, B3 represents a nitrogen atom or CR6c, and B4 represents a nitrogen atom or CR6d;
a combination in which B1 represents a nitrogen atom or CR6a, B2 represents a nitrogen atom or CR6b, B3 represents CR1, and B4 represents a nitrogen atom or CR6d;
a combination in which B1 represents a nitrogen atom or CR6a, B2 represents a nitrogen atom or CR6b, B3 represents CR6c, and B4 represents CR1;
a combination in which B1 represents a nitrogen atom or CR6a, B2 represents CR6b, B3 represents a nitrogen atom, and B4 represents CR1; or
a combination in which B1 represents CR6a, B2 represents a nitrogen atom, B3 represents a nitrogen atom, and B4 represents CR1,
R1 represents a C1-C6 chain hydrocarbon group having one or more substituents selected from the group consisting of cyano group and halogen atom, a C3-C4 cycloalkyl group optionally having one or more substituents selected from the group consisting of cyano group and halogen atom, S(O)mR8, OR8, halogen atom or OS(O)mR8,
m represents 0, 1 or 2,
R8 represents a C1-C6 chain hydrocarbon group having one or more substituents selected from the group consisting of cyano group and halogen atom; or a C3-C4 cycloalkyl group optionally having one or more substituents selected from the group consisting of cyano group and halogen atom,
R4a, R4b, R6a, R6b, R6c and R6d are identical to or different from each other and each represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, a C1-C6 alkoxy group optionally having one or more halogen atoms, NR9R10, C(O)R7, C(O)NR19R20, NR9C(O)R18, NR9C(O)OR18, NR9C(O)NR19R20, cyano group, halogen atom or a hydrogen atom,
R9 and R19 are identical to or different from each other and each represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, or a hydrogen atom,
R10 represents a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group F, a C3-C7 cycloalkyl group optionally having one or more substituents selected from Group J, a C3-C7 cycloalkenyl group optionally having one or more substituents selected from Group J, a phenyl group optionally having one or more substituents selected from Group D, a six(6) membered aromatic heterocyclic group optionally having one or more substituents selected from Group D, a hydrogen atom, or S(O)2R21,
R21 represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, or a phenyl group optionally having one or more substituents selected from Group D,
R7, R18, and R20 are identical to or different from each other and each represents a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group F, a C3-C7 cycloalkyl group optionally having one or more substituents selected from Group J, or a hydrogen atom,
n represents 0, 1 or 2,
R2 represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a cyclopropyl group, or a cyclopropylmethyl group,
G1 represents a nitrogen atom or CR3a,
G2 represents CR3b,
G3 represents a nitrogen atom or CR3c,
G4 represents a nitrogen atom or CR3d,
R3a, R3c and R3d are identical to or different from each other and each represents a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group B, a C3-C7 cycloalkyl group optionally having one or more substituents selected from Group E, a phenyl group optionally having one or more substituents selected from Group H, a 5 or 6 membered aromatic heterocyclic group optionally having one or more substituents selected from Group H, OR12, NR11R12, NR11aR12a, NR24NR11R12, NR24OR11, NR11C(O)R13, NR24NR11C(O)R13, NR11C(O)OR14, NR24NR11C(O)OR14, NR11C(O)NR31R32, NR24NR11C(O)NR31R32, N═CHNR31R32, N═S(O)pR15R16, C(O)R13, C(O)OR17, C(O)NR31R32, C(O)NR11S(O)2R23, CR30═NOR17, NR11CR24═NOR17, S(O)qR23, a cyano group, a nitro group, a hydrogen atom, or a halogen atom,
R3b represents a halogen atom,
p represents 0 or 1,
q represents 0 or 1,
R30 represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a halogen atom OR35, NR36R37, or a hydrogen atom,
R35 represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms,
R17 represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a phenyl group optionally having one or more substituents selected from Group D, or a hydrogen atom,
R11, R24, R36 and R37 are identical to or different from each other and each represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, or a hydrogen atom,
R12 represents a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group F, a C3-C7 cycloalkyl group optionally having one or more substituents selected from Group J, a C3-C7 cycloalkenyl group optionally having one or more substituents selected from Group J, a phenyl group optionally having one or more substituents selected from Group D, a 6 membered aromatic heterocyclic group optionally having one or more substituents selected from Group D, a hydrogen atom, or S(O)2R23,
R23 represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, or a phenyl group optionally having one or more substituents selected from Group D,
R11a and R12a combined together with a nitrogen atom to which they are attached represent a 3 to 7 membered nonaromatic heterocyclic group optionally having one or more substituents selected from Group E,
R13 represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group optionally having one or more halogen atoms, a phenyl group optionally having one or more substituents selected from Group D, a 5 or 6 membered aromatic heterocyclic group optionally having one or more substituents selected from Group D, or a hydrogen atom,
R14 represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C7 cycloalkyl group optionally having one or more halogen atoms, a (C3-C6 cycloalkyl)C1-C3 alkyl group optionally having one or more halogen atoms, or a phenyl C1-C3 alkyl group {the phenyl moiety in the phenyl C1-C3 alkyl group may have optionally one or more substituents selected from Group D},
R15 and R16 are identical to or different from each other and each represents a C1-C6 alkyl group optionally having one or more halogen atoms,
R31 represents a C1-C6 alkyl group optionally having one or more halogen atoms, or a hydrogen atom,
R32 represents a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group F, a C3-C7 cycloalkyl group optionally having one or more substituents selected from Group J, or a hydrogen atom,
Group B: a group consisting of a C1-C6 alkoxy group optionally having one or more halogen atoms, a C3-C6 alkenyloxy group optionally having one or more halogen atoms, a C3-C6 alkynyloxy group optionally having one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally having one or more halogen atoms, a C3-C6 cycloalkyl group optionally having one or more halogen atoms, a C1-C6 alkylamino group optionally having one or more halogen atoms, a di(C1-C4 alkyl)amino group optionally having one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally having one or more halogen atoms, a C2-C6 alkoxycarbonyl group optionally having one or more halogen atoms, a C2-C6 alkoxycarbonyloxy group optionally having one or more halogen atoms, an aminocarbonyl group, a C1-C6 alkylaminocarbonyl group optionally having one or more halogen atoms, a di(C1-C4 alkyl)aminocarbonyl group optionally having one or more halogen atoms, a C2-C6 alkoxycarbonylamino group optionally having one or more halogen atoms, a (C2-C6 alkoxycarbonyl)(C1-C6 alkyl) amino group optionally having one or more halogen atoms, a cyano group, an amino group, a nitro group, a hydroxy group, and a halogen atom,
Group D: a group consisting of a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C3-C6 alkenyloxy group optionally having one or more halogen atoms, a C3-C6 alkynyloxy group optionally having one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally having one or more halogen atoms, a C3-C6 cycloalkyl group optionally having one or more halogen atoms, a C1-C6 alkylamino group optionally having one or more halogen atoms, a di(C1-C4 alkyl)amino group optionally having one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally having one or more halogen atoms, a C2-C6 alkoxycarbonyl group optionally having one or more halogen atoms, a C2-C6 alkoxycarbonyloxy group optionally having one or more halogen atoms, an aminocarbonyl group, a C1-C6 alkylaminocarbonyl group optionally having one or more halogen atoms, a di(C1-C4 alkyl)aminocarbonyl group optionally having one or more halogen atoms, a C2-C6 alkoxycarbonylamino group optionally having one or more halogen atoms, a (C2-C6 alkoxycarbonyl)(C1-C6 alkyl) amino group optionally having one or more halogen atoms, a cyano group, an amino group, a nitro group, a hydroxy group, and a halogen atom,
Group E: a group consisting of a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C3-C6 alkenyloxy group optionally having one or more halogen atoms, a C3-C6 alkynyloxy group optionally having one or more halogen atoms, a C1-C6 alkylamino group optionally having one or more halogen atoms, a di(C1-C4 alkyl)amino group optionally having one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally having one or more halogen atoms, a C2-C6 alkoxycarbonyl group optionally having one or more halogen atoms, a C2-C6 alkoxycarbonyloxy group optionally having one or more halogen atoms, an aminocarbonyl group, a C1-C6 alkylaminocarbonyl group optionally having one or more halogen atoms, a di(C1-C4 alkyl)aminocarbonyl group optionally having one or more halogen atoms, a C2-C6 alkoxycarbonylamino group optionally having one or more halogen atoms, a (C2-C6 alkoxycarbonyl)(C1-C6 alkyl) amino group optionally having one or more halogen atoms, a cyano group, an amino group, a nitro group, a hydroxy group, an oxo group, and a halogen atom,
Group F: a group consisting of a C3-C7 cycloalkyl group optionally having one or more halogen atoms, a phenyl group optionally having one or more substituents selected from Group D, a 5 or 6 membered aromatic heterocyclic group optionally having one or more substituents selected from Group D, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C1-C6 alkylamino group optionally having one or more halogen atoms, a di(C1-C4 alkyl)amino group optionally having one or more halogen atoms, a cyano group, an amino group, a nitro group, a hydroxy group, and a halogen atom,
Group H: a group consisting of a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C6 cycloalkyl group optionally having one or more halogen atoms, a phenyl group optionally having one or more substituents selected from Group D, a 5 or 6 membered aromatic heterocyclic group optionally having one or more substituents selected from Group D, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C1-C6 alkylamino group optionally having one or more halogen atoms, a di(C1-C4 alkyl)amino group optionally having one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally having one or more halogen atoms, a C2-C6 alkoxycarbonyl group optionally having one or more halogen atoms, a C2-C6 alkoxycarbonyloxy group optionally having one or more halogen atoms, an aminocarbonyl group, a (C1-C6 alkyl)aminocarbonyl group optionally having one or more halogen atoms, a di(C1-C4 alkyl)aminocarbonyl group optionally having one or more halogen atoms, a C2-C6 alkoxycarbonylamino group optionally having one or more halogen atoms, a (C2-C6 alkoxycarbonyl)(C1-C6 alkyl) amino group optionally having one or more halogen atoms, a cyano group, an amino group, a nitro group, a hydroxy group, and a halogen atom,
Group I: a group consisting of a C2-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C3-C6 cycloalkyl group optionally having one or more halogen atoms, a phenyl group optionally having one or more substituents selected from Group D, a 5 or 6 membered aromatic heterocyclic group optionally having one or more substituents selected from Group D, a C2-C6 alkylcarbonyl group optionally having one or more halogen atoms, a C2-C6 alkoxycarbonyl group optionally having one or more halogen atoms, an aminocarbonyl group, a (C1-C6 alkyl)aminocarbonyl group optionally having one or more halogen atoms, and a di(C1-C4 alkyl)aminocarbonyl group optionally having one or more halogen atoms,
Group J: a group consisting of a C1-C6 alkyl group optionally having one or more halogen atoms, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C2-C6 alkoxycarbonyl group optionally having one or more halogen atoms, an amino group, a cyano group, and a halogen atom,
or N-oxide thereof.