US 12,172,978 B2
Ether compound and harmful arthropod-controlling composition containing same
Ayaka Tanaka, Chuo-ku (JP); Yoshihiko Nokura, Takarazuka (JP); and Yuji Nakajima, Takarazuka (JP)
Assigned to SUMITOMO CHEMICAL COMPANY, LIMITED, Chuo-ku (JP)
Appl. No. 17/432,120
Filed by SUMITOMO CHEMICAL COMPANY, LIMITED, Chuo-ku (JP)
PCT Filed Feb. 19, 2020, PCT No. PCT/JP2020/006576
§ 371(c)(1), (2) Date Aug. 19, 2021,
PCT Pub. No. WO2020/171129, PCT Pub. Date Aug. 27, 2020.
Claims priority of application No. 2019-028201 (JP), filed on Feb. 20, 2019.
Prior Publication US 2022/0135537 A1, May 5, 2022
Int. Cl. C07D 401/12 (2006.01); A01N 43/40 (2006.01); A01N 43/54 (2006.01); A01N 43/58 (2006.01); A01P 7/00 (2006.01); C07D 401/14 (2006.01)
CPC C07D 401/12 (2013.01) [A01N 43/40 (2013.01); A01N 43/54 (2013.01); A01N 43/58 (2013.01); A01P 7/00 (2021.08); C07D 401/14 (2013.01)] 11 Claims
 
1. A compound represented by formula (I) or its N oxide compound:

OG Complex Work Unit Chemistry
wherein
a combination of A1 and A2 represents
a combination wherein A1 represents a nitrogen atom or CR1b and A2 represents CR1c; or
a combination wherein A1 represents CR1b and A2 represents a nitrogen atom,
R1a, R1b and R1c are identical to or different from each other and each represents a C1-C6 alkyl group which may be optionally substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be optionally substituted with one or more halogen atoms, a C1-C6 alkylamino group which may be optionally substituted with one or more halogen atoms, a di(C1-C4 alkyl)amino group which may be optionally substituted with one or more halogen atoms, a hydroxy group, an amino group, a nitro group, a cyano group, a halogen atom, or a hydrogen atom,
R2 represents a C1-C6 alkyl group which may be optionally substituted with one or more halogen atoms, a cyclopropyl group, or a cyclopropylmethyl group,
n is 0, 1 or 2,
q is 0, 1, 2 or 3,
R3 each represents a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group A, a C3-C7 cycloalkyl group which may be optionally substituted with one or more substituents selected from Group B, a phenyl group which may be optionally substituted with one or more substituents selected from Group C, a five or six membered aromatic heterocyclic group which may be optionally substituted with one or more substituents selected from Group C, a three to seven membered nonaromatic heterocyclic group which may be optionally substituted with one or more substituents selected from Group B, OR8, NR7R8, NR7NR8R9, NR7OR9, NR7C(O)R10, NR7C(O)OR11, N═CHNR7R9, C(O)R10, C(O)OR10, C(O)NR7R8, CR7═NOR9, S(O)pR12, a cyano group, a nitro group, or a halogen atom, and when q is 2 or 3, a plural of R3 may be identical to or different from each other,
p is 0, 1 or 2,
Q represents an oxygen atom or NR4, and when n is 2, two Q may be identical to or different from each other,
R4 represents a C1-C6 alkyl group which may be optionally substituted with one or more halogen atoms, a C2-C7 alkylcarbonyl group which may be optionally substituted with one or more halogen atoms, a C2-C7 alkoxycarbonyl group which may be optionally substituted with one or more halogen atoms, a cyano group, a nitro group, or a hydrogen atom,
T represents a C1-C10 chain hydrocarbon group which is substituted with one or more halogen atoms, OR6, S(O)mR6, OS(O)2R6, NR6R7, a group represented by formula T1, a group represented by formula T2, or a group represented by formula T3,

OG Complex Work Unit Chemistry
a combination of B1, B2 and B3 represents
a combination wherein B1 represents CR5a, B2 represents a nitrogen atom or CR5b, and B3 represents a nitrogen atom or CR5c; or
a combination wherein B1 represents a nitrogen atom, B2 represents CR5b, and B3 represents a nitrogen atom or CR5c; or
a combination wherein B1 and B2 represent a nitrogen atom, and B3 represents CR5c,
B4 represents a nitrogen atom or CR5d,
B5 represents a nitrogen atom or CR5e,
B6 represents a nitrogen atom or CR5f,
B7 represents a nitrogen atom or CR5g,
R5a, R5b, R5c, R5d, R5e, R5f and R5g are identical to or different from each other and each represent a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more halogen atoms, a C3-C6 cycloalkyl group which may be optionally substituted with one or more halogen atoms, a halogen atom, or a hydrogen atom,
R6a represents a C1-C5 chain hydrocarbon group which is substituted with one or more halogen atoms, OR12, OS(O)2R12, S(O)mR12, or a halogen atom,
m is 0, 1 or 2,
R12 represents a C1-C6 chain hydrocarbon group which is substituted with one or more halogen atoms,
R6 represents a C1-C10 chain hydrocarbon group which is substituted with one or more substituents selected from the group consisting of cyano group and halogen atom; or a (C3-C7 cycloalkyl) C1-C3 alkyl group which is substituted with one or more substituents selected from the group consisting of cyano group, halogen atom and C1-C6 haloalkyl group,
R7 and R9 are identical to or different from each other and each represent a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more halogen atoms, or a hydrogen atom,
R8 represents a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group A, a C3-C7 cycloalkyl group which may be optionally substituted with one or more substituents selected from Group B, a phenyl group which may be optionally substituted with one or more substituents selected from Group C, a five or six membered aromatic heterocyclic group which may be optionally substituted with one or more substituents selected from Group C, a C1-C6 alkylsulfonyl group which may be optionally substituted with one or more halogen atoms, or a hydrogen atom,
R10 represents a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more halogen atoms, a C3-C7 cycloalkyl group which may be optionally substituted with one or more halogen atoms, a (C3-C6 cycloalkyl) C1-C3 alkyl group which may be optionally substituted with one or more halogen atoms, a phenyl group which may be optionally substituted with one or more substituents selected from Group C, a five or six membered aromatic heterocyclic group which may be optionally substituted with one or more substituents selected from Group C, or a hydrogen atom,
R11 represents a C1-C6 chain hydrocarbon group which may be optionally substituted with one or more halogen atoms, a C3-C7 cycloalkyl group which may be optionally substituted with one or more halogen atoms, a (C3-C6 cycloalkyl) C1-C3 alkyl group which may be optionally substituted with one or more halogen atoms, a phenyl group which may be optionally substituted with one or more substituents selected from Group C, or a five or six membered aromatic heterocyclic group which may be optionally substituted with one or more substituents selected from Group C,
Group A is the group consisting of a C1-C6 alkoxy group which may be optionally substituted with one or more halogen atoms, a C3-C6 alkenyloxy group which may be optionally substituted with one or more halogen atoms, a C3-C6 alkynyloxy group which may be optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be optionally substituted with one or more halogen atoms, a C1-C6 alkylamino group which may be optionally substituted with one or more halogen atoms, a di(C1-C4 alkyl)amino group which may be optionally substituted with one or more halogen atoms, a C3-C6 cycloalkyl group which may be optionally substituted with one or more halogen atoms, a phenyl group, a five or six membered aromatic heterocyclic group, an amino group, a cyano group, a hydroxy group, a sulfanyl group, and a halogen atom, wherein the phenyl group and the five or six membered aromatic heterocyclic group may be optionally substituted with one or more substituents selected from the group consisting of C1-C6 alkyl group which may be optionally substituted with one or more halogen atoms, C1-C6 alkoxy group which may be optionally substituted with one or more halogen atoms, cyano group, nitro group, and halogen atom,
Group B is the group consisting of a C1-C6 alkyl group which may be optionally substituted with one or more halogen atoms, a halogen atom, and a cyano group, and
Group C is the group consisting of a C1-C6 alkyl group which may be optionally substituted with one or more halogen atoms, a C1-C6 alkoxy group which may be optionally substituted with one or more halogen atoms, a C3-C6 alkenyloxy group which may be optionally substituted with one or more halogen atoms, a C3-C6 alkynyloxy group which may be optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfanyl group which may be optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfinyl group which may be optionally substituted with one or more halogen atoms, a C1-C6 alkylsulfonyl group which may be optionally substituted with one or more halogen atoms, a C1-C6 alkylamino group which may be optionally substituted with one or more halogen atoms, a di(C1-C4 alkyl)amino group which may be optionally substituted with one or more halogen atoms, a C2-C7 alkylcarbonyl group which may be optionally substituted with one or more halogen atoms, a C2-C7 alkoxycarbonyl group which may be optionally substituted with one or more halogen atoms, an amino group, a cyano group, a nitro group, a hydroxy group, a sulfanyl group, and a halogen atom.