US 12,144,350 B2
Heterocyclic compound and harmful arthropod control composition containing same
Masayuki Tashiro, Takarazuka (JP); Ayaka Tanaka, Chuo-ku (JP); and Shinichiro Murakami, Chuo-ku (JP)
Assigned to SUMITOMO CHEMICAL COMPANY, LIMITED, Chuo-ku (JP)
Appl. No. 17/426,938
Filed by SUMITOMO CHEMICAL COMPANY, LIMITED, Chuo-ku (JP)
PCT Filed Jan. 30, 2020, PCT No. PCT/JP2020/003521
§ 371(c)(1), (2) Date Jul. 29, 2021,
PCT Pub. No. WO2020/158889, PCT Pub. Date Aug. 6, 2020.
Claims priority of application No. 2019-015345 (JP), filed on Jan. 31, 2019; application No. 2019-117011 (JP), filed on Jun. 25, 2019; and application No. 2019-222703 (JP), filed on Dec. 10, 2019.
Prior Publication US 2022/0095620 A1, Mar. 31, 2022
Int. Cl. C07D 519/00 (2006.01); A01N 43/90 (2006.01); A01P 7/00 (2006.01)
CPC A01N 43/90 (2013.01) [A01P 7/00 (2021.08); C07D 519/00 (2013.01)] 15 Claims
 
1. A compound represented by formula (I)

OG Complex Work Unit Chemistry
wherein:
R2 represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a cyclopropyl group, or a cyclopropylmethyl group;
n represents 0, 1, or 2;
G1 represents a nitrogen atom or CR3a;
G2 represents a nitrogen atom or CR3b;
G3 represents a nitrogen atom or CR3c;
G4 represents a nitrogen atom or CR3d;
R3a, R3b, R3c, and R3d are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group B, a C3-C7 cycloalkyl group optionally substituted with one or more substituent(s) selected from Group E, a phenyl group optionally substituted with one or more substituent(s) selected from Group H, a 5 or 6 membered aromatic heterocyclic group optionally substituted with one or more substituent(s) 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)mR23, a cyano group, a nitro group, a hydrogen atom, or a halogen atom;
p represents 0 or 1;
m represents 0, 1, or 2;
R30 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a halogen atom, OR35, NR36R37, or a hydrogen atom;
R35 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s);
R17 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a phenyl group optionally substituted with one or more substituent(s) selected from Group D, or a hydrogen atom;
R11, R24, R36, and R37 are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), or a hydrogen atom;
R12 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group F, a C3-C7 cycloalkyl group optionally substituted with one or more substituent(s) selected from Group J, a C3-C7 cycloalkenyl group optionally substituted with one or more substituent(s) selected from Group J, a phenyl group optionally substituted with one or more substituent(s) selected from Group D, a 6 membered aromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group D, a hydrogen atom, or S(O)2R23;
R23 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), or a phenyl group optionally substituted with one or more substituent(s) selected from Group D;
R11a and R12a are combined with the nitrogen atom to which they are attached to form a 3-7 membered nonaromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group E;
R13 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a C3-C7 cycloalkyl group optionally substituted with one or more halogen atom(s), a (C3-C6 cycloalkyl) C1-C3 alkyl group optionally substituted with one or more halogen atom(s), a phenyl group optionally substituted with one or more substituent(s) selected from Group D, a 5 or 6 membered aromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group D, or a hydrogen atom;
R14 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a C3-C7 cycloalkyl group optionally substituted with one or more halogen atom(s), a (C3-C6 cycloalkyl) C1-C3 alkyl group optionally substituted with one or more halogen atom(s), or a phenyl C1-C3 alkyl group, wherein the phenyl moiety in said phenyl C1-C3 alkyl group is optionally substituted with one or more substituent(s) selected from Group D;
R15 and R16 are identical to or different from each other, and each represent a C1-C6 alkyl group optionally substituted with one or more halogen atom(s);
R31 represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), or a hydrogen atom;
R32 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group F, a C3-C7 cycloalkyl group optionally substituted with one or more substituent(s) selected from Group J, S(O)2R23, or a hydrogen atom;
Q represents a group represented by Q1 or a group represented by Q2;

OG Complex Work Unit Chemistry
Z represents an oxygen atom or a sulfur atom;
the combination of A2 and A3 represents:
a combination wherein A2 represents CR4a, and A3 represents a nitrogen atom or CR4b; or
a combination wherein A2 represents a nitrogen atom, and A3 represents CR4b;
the combination of B1, B2, and B3 represents:
a combination wherein B1 represents CR1, B2 represents a nitrogen atom or CR6b, and B3 represents a nitrogen atom or CR6c;
a combination wherein B1 represents a nitrogen atom or CR6a, B2 represents CR1, and B3 represents a nitrogen atom or CR6c; or
a combination wherein B1 represents a nitrogen atom or CR6a, B2 represents a nitrogen atom or CR6b, and B3 represents CR1;
R1 represents a C1-C6 chain hydrocarbon group substituted with one or more substituent(s) selected from the group consisting of a cyano group and a halogen atom, a C3-C4 cycloalkyl group optionally substituted with one or more substituent(s) selected from the group consisting of a cyano group and a halogen atom, SR8, S(O)R8, S(O)2R8, OR8, or OS(O)2R8;
R8 represents a C1-C6 chain hydrocarbon group substituted with one or more substituent(s) selected from the group consisting of a cyano group and a halogen atom, or a C3-C4 cycloalkyl group optionally substituted with one or more substituent(s) selected from the group consisting of a cyano group and a halogen atom;
R4a, R4b, R6a, R6b, and R6c are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a C3-C7 cycloalkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), NR25R26, C(O)R7, C(O)OR7, C(O)NR19R20, NR25C(O)R18, NR25C(O)OR18, NR25C(O)NR19R20, a cyano group, a halogen atom, or a hydrogen atom;
R19 and R25 are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), or a hydrogen atom;
R26 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group L, a C3-C7 cycloalkyl group optionally substituted with one or more substituent(s) selected from Group M, a C3-C7 cycloalkenyl group optionally substituted with one or more substituent(s) selected from Group M, a phenyl group optionally substituted with one or more substituent(s) selected from Group K, a 6 membered aromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group K, a hydrogen atom, or S(O)2R27;
R27 represents a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a C3-C7 cycloalkyl group optionally substituted with one or more halogen atom(s), or a phenyl group optionally substituted with one or more substituent(s) selected from Group K; and
R7, R18, and R20 are identical to or different from each other, and each represent a C1-C6 chain hydrocarbon group optionally substituted with one or more substituent(s) selected from Group L, a C3-C7 cycloalkyl group optionally substituted with one or more substituent(s) selected from Group M, or a hydrogen atom;
Group B: a group consisting of a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C3-C6 alkenyloxy group optionally substituted with one or more halogen atom(s), a C3-C6 alkynyloxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atom(s), a C3-C6 cycloalkyl group optionally substituted with one or more halogen atom(s), a cyano group, a hydroxy group, and a halogen atom;
Group C: a group consisting of a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C3-C6 alkenyloxy group optionally substituted with one or more halogen atom(s), a C3-C6 alkynyloxy group optionally substituted with one or more halogen atom(s), and a halogen atom;
Group D: a group consisting of a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a hydroxy group, a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C3-C6 alkenyloxy group optionally substituted with one or more halogen atom(s), a C3-C6 alkynyloxy group optionally substituted with one or more halogen atom(s), a sulfanyl group, a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atom(s), an amino group, NHR21, NR21R22, C(O)R21, OC(O)R21, C(O)OR21, a cyano group, a nitro group, and a halogen atom;
R21 and R22 are identical to or different from each other, and each represent a C1-C6 alkyl group optionally substituted with one or more halogen atom(s);
Group E: a group consisting of a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C3-C6 alkenyloxy group optionally substituted with one or more halogen atom(s), a C3-C6 alkynyloxy group optionally substituted with one or more halogen atom(s), a halogen atom, an oxo group, a hydroxy group, a cyano group, and a nitro group;
Group F: a group consisting of a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a phenyl group optionally substituted with one or more substituent(s) selected from Group D, a 5 or 6 membered aromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group D, a C3-C7 cycloalkyl group optionally substituted with one or more halogen atom(s), a 3-7 membered nonaromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group C, an amino group, NHR21, NR21R22, a halogen atom, and a cyano group;
Group H: a group consisting of a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a 5 or 6 membered aromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group D, OR10, NR9R10, C(O)R10, C(O)NR9R10, OC(O)R9, OC(O)OR9, NR10C(O)R9, NR10C(O)OR9, C(O)OR10, a halogen atom, a nitro group, a cyano group, and an amino group;
R9 represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), or a C3-C6 cycloalkyl group optionally substituted with one or more halogen atom(s);
R10 represents a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C3-C6 cycloalkyl group optionally substituted with one or more halogen atom(s), or a hydrogen atom:
Group J: a group consisting of a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a halogen atom, and a cyano group;
Group K: a group consisting of a C1-C6 chain hydrocarbon group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C3-C6 alkenyloxy group optionally substituted with one or more halogen atom(s), a C3-C6 alkynyloxy group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfanyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfinyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkylsulfonyl group optionally substituted with one or more halogen atom(s), a C3-C6 cycloalkyl group optionally substituted with one or more halogen atom(s), a (C1-C6 alkyl optionally substituted with one or more halogen atom(s))amino group, a di(C1-C4 alkyl)amino group optionally substituted with one or more halogen atom(s), a C2-C6 alkylcarbonyl group optionally substituted with one or more halogen atom(s), a C2-C6 alkoxycarbonyl group optionally substituted with one or more halogen atom(s), a C2-C6 alkoxycarbonyloxy group optionally substituted with one or more halogen atom(s), an aminocarbonyl group, a (C1-C6 alkyl optionally substituted with one or more halogen atom(s))aminocarbonyl group, a [di(C1-C4 alkyl)amino optionally substituted with one or more halogen atom(s)]carbonyl group, a (C2-C6 alkoxycarbonyl optionally substituted with one or more halogen atom(s))amino group, a (C2-C6 alkoxycarbonyl)(C1-C6 alkyl)amino group optionally substituted with one or more halogen atom(s), a cyano group, an amino group, a nitro group, a hydroxy group, and a halogen atom;
Group L: a group consisting of a C3-C6 cycloalkyl group optionally substituted with one or more halogen atom(s), a phenyl group optionally substituted with one or more substituent(s) selected from Group K, a 5 or 6 membered aromatic heterocyclic group optionally substituted with one or more substituent(s) selected from Group K, a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a (C1-C6 alkyl optionally substituted with one or more halogen atom(s))amino group, a di(C1-C4 alkyl)amino group optionally substituted with one or more halogen atom(s), a cyano group, an amino group, a nitro group, a hydroxy group, and a halogen atom;
Group M: a group consisting of a C1-C6 alkyl group optionally substituted with one or more halogen atom(s), a C1-C6 alkoxy group optionally substituted with one or more halogen atom(s), a C2-C6 alkoxycarbonyl group optionally substituted with one or more halogen atom(s), an amino group, a cyano group, and a halogen atom,
or an N-oxide thereof.