US 12,221,431 B2
Heterocyclic compound
Takamasa Tanabe, Takarazuka (JP); Yoshihiko Nokura, Takarazuka (JP); Kohei Orimoto, Takarazuka (JP); and Yuji Nakajima, Takarazuka (JP)
Assigned to SUMITOMO CHEMICAL COMPANY, LIMITED, Tokyo (JP)
Filed by Sumitomo Chemical Company, Limited, Tokyo (JP)
Filed on Jul. 23, 2021, as Appl. No. 17/383,432.
Application 17/383,432 is a division of application No. 16/079,348, granted, now 11,124,492, previously published as PCT/JP2017/005837, filed on Feb. 17, 2017.
Claims priority of application No. 2016-036956 (JP), filed on Feb. 29, 2016.
Prior Publication US 2021/0347757 A1, Nov. 11, 2021
Int. Cl. C07D 401/04 (2006.01); A01N 43/40 (2006.01); A01N 43/54 (2006.01); A01N 43/58 (2006.01); A01N 43/60 (2006.01); C07D 213/32 (2006.01); C07D 213/34 (2006.01); C07D 213/38 (2006.01); C07D 213/61 (2006.01); C07D 213/70 (2006.01); C07D 213/71 (2006.01); C07D 213/74 (2006.01); C07D 213/75 (2006.01); C07D 213/82 (2006.01)
CPC C07D 401/04 (2013.01) [A01N 43/40 (2013.01); A01N 43/54 (2013.01); A01N 43/58 (2013.01); A01N 43/60 (2013.01); C07D 213/32 (2013.01); C07D 213/34 (2013.01); C07D 213/38 (2013.01); C07D 213/61 (2013.01); C07D 213/70 (2013.01); C07D 213/71 (2013.01); C07D 213/74 (2013.01); C07D 213/75 (2013.01); C07D 213/82 (2013.01)] 15 Claims
 
1. A compound represented by formula (I):

OG Complex Work Unit Chemistry
or an N-oxide compound thereof,
wherein:
A1 represents a nitrogen atom or a CR4;
R4 represents a hydrogen atom, a OR27, a NR27R28, a cyano group, a nitro group, or a halogen atom;

OG Complex Work Unit Chemistry
hereinafter referred to as “Het”, represents Het-2, Het-3, or Het-4:

OG Complex Work Unit Chemistry
wherein #1 represents a covalent bond between Het and T, and #2 represents the binding position of Het and

OG Complex Work Unit Chemistry
T represents T-1, T-2, T-3, T-4, T-5, T-6, or T-7:

OG Complex Work Unit Chemistry
R1 represents a C1-C10 chain hydrocarbon group having one or more halogen atoms, a (C1-C5 alkoxy) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfanyl) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfinyl) C2-C5 alkyl group having one or more halogen atoms, a (C1-C5 alkylsulfonyl) C2-C5 alkyl group having one or more halogen atoms, a (C3-C7 cycloalkyl) C1-C3 alkyl group having one or more substituents selected from Group G, or a C3-C7 cycloalkyl group having one or more substituents selected from Group G;
R2 represents a C1-C6 alkyl group optionally having one or more halogen atoms, a cyclopropylmethyl group, or a cyclopropyl group;
q represents 0, 1, 2, or 3;
R3 represents a C1-C6 chain hydrocarbon group optionally having one or more substituents selected from Group B, 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 OR12, a NR11R12, a NR11aR12a, a NR24NR11R12, a NR24OR11, a NR11C(O) R13, a NR24NR11C(O) R13, a NR11C(O) OR14, a NR24NR11C(O) OR14, a NR11C(O) NR15R16, a NR24NR11C(O) NR15R16, a N═CHNR15R16, a N═S(O)xR15R16, a S(O)yR15, a C(O)OR17, a C(O)NR11R12, a cyano group, a nitro group, or a halogen atom, and wherein when q is 2 or 3, two or three R3 may be identical to or different from each other;
p represents 0, 1, or 2;
R6 represents a C1-C6 alkyl group optionally having one or more halogen atoms, a OR18, a NR18R19, a cyano group, a nitro group, or a halogen atom, wherein when p represents 2, two R6 may be identical to or different from each other;
R11, R17, R18, R19, R24, and R29 represent each independently a hydrogen atom or a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;
R32 represents a hydrogen atom, a halogen atom, a OR33, a NR34R35, or a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;
R33 represents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;
R34 and R35 represent each independently a hydrogen atom or a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;
R12 represents a hydrogen atom, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 alkyl group having one substituent selected from Group F, or a 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 are combined with the nitrogen atom to which they are attached to represent a 3-7 membered nonaromatic heterocyclic group optionally having one or more substituents selected from Group E wherein said 3-7 membered nonaromatic heterocyclic group represents an aziridine ring, an azetidine ring, a pyrrolidine ring, an imidazoline ring, an imidazolidine ring, a piperidine ring, a tetrahydropyrimidine ring, a hexahydropyrimidine ring, a piperazine ring, an azepane ring, an oxazolidine ring, an isoxazolidine ring, a 1,3-oxazinane ring, a morpholine ring, a 1,4-oxazepane ring, a thiazolidine ring, an isothiazolidine ring, a 1,3-thiazinane ring, a thiomorpholine ring, or a 1,4-thiazepane ring;
R13 represents a hydrogen atom, 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, or a 5 or 6 membered aromatic heterocyclic group optionally having one or more substituents selected from Group D;
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 wherein the phenyl moiety in the phenyl C1-C3 alkyl group may optionally have one or more substituents selected from Group D;
R15 and R16 represent each independently a C1-C6 alkyl group optionally having one or more halogen atoms;
R27 and R28 represent each independently a hydrogen atom or a C1-C6 alkyl group optionally having one or more halogen atoms;
n and y represent each independently 0, 1, or 2; and
x represents 0 or 1;
Group B represents 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 cyano group, a hydroxy group, and a halogen atom;
Group D represents a group consisting of a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a hydroxy group, 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 sulfanyl group, 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, an amino group, a NHR21, a NR21R22, a C(O)R21 group, a OC(O)R21 group, a C(O)OR21 group, a cyano group, a nitro group, and a halogen atom wherein R21 and R22 represent each independently a C1-C6 alkyl group optionally having one or more halogen atoms;
Group E represents 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 halogen atom, an oxo group, a hydroxy group, a cyano group, and a nitro group;
Group F represents a group consisting of a C1-C6 alkoxy group optionally having one or more halogen atoms, an amino group, a NHR21, a NR21R22, a cyano group, 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 C3-C7 cycloalkyl group optionally having one or more halogen atoms, and a 3-7 membered nonaromatic heterocyclic group optionally having one or more substituents selected from Group C;
Group C represents 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, and a halogen atom; and
Group G represents a group consisting of a halogen atom and a C1-C6 haloalkyl group.