Substituted pyridines as noxious arthropod control agents

A compound represented by formula (I):

• or an N-oxide thereof,
• wherein:
• A1 represents N;
• Q represents formula Q1 or formula Q2:
• A2 represents CR6b or N;
• A3 represents CR6c or N;
• (i) A4 represents CR6d or N;
• and
• A5 represents CR1b;
• or
• (ii) A4 represents CR1a;
• and
• A5 represents CR6e or N;
• A6 represents CR6f or N;
• A7 represents CR6hR6i, NR6g, or O;
• Z represents O or S;
• R1a represents a C1-C6 chain hydrocarbon, OR8, OS(O)2R8, SR8, S(O)R8, S(O)2R8, or a C3-C4 cycloalkyl;
• wherein the C1-C6 chain hydrocarbon is substituted with one or more substituents independently selected from the group consisting of halogen and CN;
• and
• wherein the C3-C4 cycloalkyl is optionally substituted with one or more substituents independently selected from the group consisting of halogen and CN;
• R1b represents a C1-C6 chain hydrocarbon, OR8, OS(O)2R8, SR8, S(O)R8, S(O)2R8, or a C3-C4 cycloalkyl;
• wherein the C1-C6 chain hydrocarbon is substituted with one or more substituents independently selected from the group consisting of halogen and CN;
• and
• wherein the C3-C4 cycloalkyl is optionally substituted with one or more substituents independently selected from the group consisting of halogen and CN;
• R2 represents a C1-C6 chain hydrocarbon, CH2-cyclopropyl, or cyclopropyl, wherein the C1-C6 chain hydrocarbon is optionally substituted with one or more independently selected halogen substituents;
• each R3 independently represents halogen, CN, NO2, a C1-C6 chain hydrocarbon, CR24═NOR17, C(O)R13, C(O)NR15aR16a, C(O)NR11S(O)2R23, C(O)OR17, NR11R12, NR11aR12a, NR11CR24═NOR17, NR11C(O)R13, NR11C(O)NR15aR16a, N11C(O)OR14, NR24NR11R12, NR24NR11C(O)R13, NR24NR11C(O)NR15aR16a, NR24NR11C(O)OR14, NR24OR11, N═CR24NR15aR16a, N═S(O)xR15R16, OR12, a C3-C7 cycloalkyl, a C3-C7 cycloalkenyl, phenyl, or a 5- or 6-membered heteroaryl;
• wherein each C1-C6 chain hydrocarbon is optionally and independently substituted with one or more substituents independently selected from Group B;
• wherein each C3-C7 cycloalkyl is optionally and independently substituted with one or more substituents independently selected from Group E;
• wherein each C3-C7 cycloalkenyl is optionally and independently substituted with one or more substituents independently selected from Group J;
• and
• wherein each phenyl and 5- or 6-membered heteroaryl is optionally and independently substituted with one or more substituents independently selected from Group H;
• R6b represents H, halogen, a C1-C6 chain hydrocarbon, or a C3-C7 cycloalkyl, wherein the C1-C6 chain hydrocarbon or the C3-C7 cycloalkyl is optionally substituted with one or more independently selected halogen substituents;
• R6c represents H, halogen, CN, a C1-C6 chain hydrocarbon, C(O)R7, C(O)NR19R20, C(O)OR7, NR9R10, NR9C(O)R18, NR9C(O)NR19R20, NR9C(O)OR18, OC1-C6 alkyl, or a C3-C7 cycloalkyl, wherein the C1-C6 chain hydrocarbon, OC1-C6 alkyl, or the C3-C7 cycloalkyl is optionally substituted with one or more independently selected halogen substituents;
• R6d represents H, halogen, CN, a C1-C6 chain hydrocarbon, C(O)R7, C(O)NR19R20, C(O)OR7, NR9R10, NR9C(O)R18, NR9C(O)NR19R20, NR9C(O)OR18, OC1-C6 alkyl, or a C3-C7 cycloalkyl, wherein the C1-C6 chain hydrocarbon, OC1-C6 alkyl, or the C3-C7 cycloalkyl is optionally substituted with one or more independently selected halogen substituents;
• R6e represents H, halogen, CN, a C1-C6 chain hydrocarbon, C(O)R7, C(O)NR19R20, C(O)OR7, NR9R10, NR9C(O)R18, NR9C(O)NR19R20, NR9C(O)OR18, OC1-C6 alkyl, or a C3-C7 cycloalkyl, wherein the C1-C6 chain hydrocarbon, OC1-C6 alkyl, or the C3-C7 cycloalkyl is optionally substituted with one or more independently selected halogen substituents;
• R6f represents H, halogen, CN, a C1-C6 chain hydrocarbon, C(O)R7, C(O)NR19R20, C(O)OR7, NR9R10, NR9C(O)R18, NR9C(O)NR19R20, NR9C(O)OR18, OC1-C6 alkyl, or a C3-C7 cycloalkyl, wherein the C1-C6 chain hydrocarbon, OC1-C6 alkyl, or the C3-C7 cycloalkyl is optionally substituted with one or more independently selected halogen substituents;
• R6g represents H or a C1-C6 chain hydrocarbon, wherein the C1-C6 chain hydrocarbon is optionally substituted with one or more independently selected halogen substituents;
• R6h represents H, halogen, a C1-C6 chain hydrocarbon, or a C3-C7 cycloalkyl, wherein the C1-C6 chain hydrocarbon or the C3-C7 cycloalkyl is optionally substituted with one or more independently selected halogen substituents;
• R6i represents H, halogen, a C1-C6 chain hydrocarbon, or a C3-C7 cycloalkyl, wherein the C1-C6 chain hydrocarbon or the C3-C7 cycloalkyl is optionally substituted with one or more independently selected halogen substituents;
• R7 represents H, a C1-C6 chain hydrocarbon, or a C3-C7 cycloalkyl;
• wherein the C1-C6 chain hydrocarbon is optionally substituted with one or more substituents independently selected from Group F;
• and
• wherein the C3-C7 cycloalkyl is optionally substituted with one or more substituents independently selected from Group J;
• each R8 independently represents a C1-C6 chain hydrocarbon or a C3-C4 cycloalkyl;
• wherein each C1-C6 chain hydrocarbon is independently substituted with one or more substituents independently selected from the group consisting of halogen and CN;
• and
• wherein each C3-C4 cycloalkyl is optionally and independently substituted with one or more substituents independently selected from the group consisting of halogen and CN;
• R9 represents H or a C1-C6 chain hydrocarbon, wherein the C1-C6 chain hydrocarbon is optionally substituted with one or more independently selected halogen substituents;
• R10 represents H, a C1-C6 chain hydrocarbon, S(O)2R21, a C3-C7 cycloalkyl, a C3-C7 cycloalkenyl, phenyl, or a 6-membered heteroaryl;
• wherein the C1-C6 chain hydrocarbon is optionally substituted with one or more substituents independently selected from Group F;
• wherein the C3-C7 cycloalkyl or C3-C7 cycloalkenyl is optionally substituted with one or more substituents independently selected from Group J;
• and
• wherein the phenyl or 6-membered heteroaryl is optionally substituted with one or more substituents independently selected from Group D;
• each R11 independently represents H or a C1-C6 chain hydrocarbon, wherein each C1-C6 chain hydrocarbon is optionally and independently substituted with one or more independently selected halogen substituents;
• each R12 independently represents H, a C1-C6 chain hydrocarbon, S(O)2R23, a C3-C7 cycloalkyl, a C3-C7 cycloalkenyl, phenyl, or a 6-membered heteroaryl;
• wherein each C1-C6 chain hydrocarbon is optionally and independently substituted with one or more substituents independently selected from Group F;
• wherein each C3-C7 cycloalkyl and C3-C7 cycloalkenyl is optionally and independently substituted with one or more substituents independently selected from Group J;
• and
• wherein each phenyl and 6-membered heteroaryl is optionally and independently substituted with one or more substituents independently selected from Group D;
• each R11a and R12a, taken together with the nitrogen atom to which they are attached, independently forms a non-aromatic 3- to 7-membered heterocyclyl, wherein each 3- to 7-membered heterocyclyl is optionally and independently substituted with one or more substituents independently selected from Group E;
• each R13 independently represents H, a C1-C6 chain hydrocarbon, C1-C3 alkylene-C3-C6 cycloalkyl, a C3-C7 cycloalkyl, phenyl, or a 5- or 6-membered heteroaryl;
• wherein each C1-C6 chain hydrocarbon, C1-C3 alkylene-C3-C6 cycloalkyl, and C3-C7 cycloalkyl is optionally and independently substituted with one or more independently selected halogen substituents;
• and
• wherein each phenyl and 5- or 6-membered heteroaryl is optionally and independently substituted with one or more substituents independently selected from Group D;
• each R14 independently represents a C1-C6 chain hydrocarbon, C1-C3 alkylene-C3-C6 cycloalkyl, C1-C3 alkylene-phenyl, a C3-C7 cycloalkyl, or phenyl;
• wherein each C1-C6 chain hydrocarbon, C1-C3 alkylene-C3-C6 cycloalkyl, and C3-C7 cycloalkyl is optionally and independently substituted with one or more independently selected halogen substituents;
• and
• wherein each phenyl of each C1-C3 alkylene-phenyl is optionally and independently substituted with one or more substituents independently selected from Group D;
• each R15 independently represents a C1-C6 alkyl, wherein each C1-C6 alkyl is optionally and independently substituted with one or more independently selected halogen substituents;
• each R15a independently represents H or a C1-C6 chain hydrocarbon, wherein each C1-C6 chain hydrocarbon is optionally and independently substituted with one or more independently selected halogen substituents;
• each R16 independently represents a C1-C6 alkyl, wherein each C1-C6 alkyl is optionally and independently substituted with one or more independently selected halogen substituents;
• each R16a independently represents H, a C1-C6 chain hydrocarbon, or a C3-C7 cycloalkyl;
• wherein each C1-C6 chain hydrocarbon is optionally and independently substituted with one or more substituents independently selected from Group F;
• and
• wherein each C3-C7 cycloalkyl is optionally and independently substituted with one or more substituents independently selected from Group J;
• each R17 independently represents H, a C1-C6 chain hydrocarbon, or phenyl wherein each C1-C6 chain hydrocarbon is optionally and independently substituted with one or more substituents independently selected from Group F;
• and
• wherein each phenyl is optionally and independently substituted with one or more substituents independently selected from Group D;
• R18 represents H, a C1-C6 chain hydrocarbon, or a C3-C7 cycloalkyl;
• wherein the C1-C6 chain hydrocarbon is optionally substituted with one or more substituents independently selected from Group F;
• and
• wherein the C3-C7 cycloalkyl is optionally substituted with one or more substituents independently selected from Group J;
• R19 represents H or a C1-C6 chain hydrocarbon, wherein the C1-C6 chain hydrocarbon is optionally substituted with one or more independently selected halogen substituents;
• R20 represents H, a C1-C6 chain hydrocarbon, or a C3-C7 cycloalkyl;
• wherein the C1-C6 chain hydrocarbon is optionally substituted with one or more substituents independently selected from Group F;
• and
• wherein the C3-C7 cycloalkyl is optionally substituted with one or more substituents independently selected from Group J;
• R21 represents a C1-C6 chain hydrocarbon, a C3-C7 cycloalkyl, or phenyl;
• wherein the C1-C6 chain hydrocarbon or the C3-C7 cycloalkyl is optionally substituted with one or more independently selected halogen substituents;
• and
• wherein the phenyl is optionally substituted with one or more substituents independently selected from Group D;
• each R23 independently represents a C1-C6 chain hydrocarbon, a C3-C7 cycloalkyl, or phenyl;
• wherein each C1-C6 chain hydrocarbon and C3-C7 cycloalkyl is optionally and independently substituted with one or more independently selected halogen substituents;
• and
• wherein each phenyl is optionally and independently substituted with one or more substituents independently selected from Group D;
• each R24 independently represents H or a C1-C6 chain hydrocarbon, wherein each C1-C6 chain hydrocarbon is optionally and independently substituted with one or more independently selected halogen substituents;
• n is 0, 1, or 2;
• q is 0, 1, 2, or 3;
• and
• each x is independently 0 or 1;
• wherein Group B, Group D, Group E, Group F, Group G, Group H, and Group J are as follows:
• each Group B substituent is selected from the group consisting of halogen, CN, NO2, C(O)NH2, C(O)NHC1-C6 alkyl, C(O)C2-C6 alkyl, C(O)N(C1-C4 alkyl)2, C(O)OC2-C6 alkyl, NH2, NHC1-C6 alkyl, NHC(O)OC2-C6 alkyl, N(C1-C4 alkyl)2, N(C1-C6 alkyl)C(O)OC2-C6 alkyl, OH, OC1-C6 alkyl, OC3-C6 alkenyl, OC3-C6 alkynyl, OC(O)OC2-C6 alkyl, SC1-C6 alkyl, S(O)C1-C6 alkyl, S(O)2C1-C6 alkyl, and a C3-C6 cycloalkyl, wherein each C(O)NHC1-C6 alkyl, C(O)C2-C6 alkyl, C(O)N(C1-C4 alkyl)2, C(O)OC2-C6 alkyl, NHC1-C6 alkyl, NHC(O)OC2-C6 alkyl, N(C1-C4 alkyl)2, N(C1-C6 alkyl)C(O)OC2-C6 alkyl, OC1-C6 alkyl, OC3-C6 alkenyl, OC3-C6 alkynyl, OC(O)OC2-C6 alkyl, SC1-C6 alkyl, S(0)C1-C6 alkyl, S(O)2C1-C6 alkyl, and a C3-C6 cycloalkyl is optionally and independently substituted with one or more independently selected halogen substituents;
• each group D substituent is selected from the group consisting of halogen, CN, NO2, a C1-C6 hydrocarbon chain, C(O)NH2, C(O)NHC1-C6 alkyl, C(O)C2-C6 alkyl, C(O)N(C1-C4 alkyl)2, C(O)OC2-C6 alkyl, NH2, NHC1-C6 alkyl, NHC(O)OC2-C6 alkyl, N(C1-C4 alkyl)2, N(C1-C6 alkyl) C(O)OC2-C6 alkyl, OH, OC1-C6 alkyl, OC3-C6 alkenyl, OC3-C6 alkynyl, OC(O)OC2-C6 alkyl, SC1-C6 alkyl, S(0)C1-C6 alkyl, S(O)2C1-C6 alkyl, and a C3-C6 cycloalkyl, wherein each C1-C6 hydrocarbon chain, C(O)C2-C6 alkyl, C(O)NHC1-C6 alkyl, C(O)N(C1-C4 alkyl)2, C(O)OC2-C6 alkyl, NHC1-C6 alkyl, NHC(O)OC2-C6 alkyl, N(C1-C4 alkyl)2, N(C1-C6 alkyl) C(O)OC2-C6 alkyl, OC1-C6 alkyl, OC3-C6 alkenyl, OC3-C6 alkynyl, OC(O)OC2-C6 alkyl, SC1-C6 alkyl, S(0)C1-C6 alkyl, S(O)2C1-C6 alkyl, and C3-C6 cycloalkyl is optionally and independently substituted with one or more independently selected halogen substituents;
• each Group E substituent is selected from the group consisting of halogen, CN, NO2, a C1-C6 hydrocarbon chain, C(O)NH2, C(O)NHC1-C6 alkyl, C(O)C2-C6 alkyl, C(O)N(C1-C4 alkyl)2, C(O)OC2-C6 alkyl, NH2, NHC1-C6 alkyl, NHC(O)OC2-C6 alkyl, N(C1-C4 alkyl)2, N(C1-C6 alkyl)C(O)OC2-C6 alkyl, OH, OC1-C6 alkyl, OC3-C6 alkenyl, OC3-C6 alkynyl, OC(O)OC2-C6 alkyl, and ═O, wherein each C1-C6 hydrocarbon chain, C(O)C2-C6 alkyl, C(O)NHC1-C6 alkyl, C(O)N(C1-C4 alkyl)2, C(O)OC2-C6 alkyl, NHC1-C6 alkyl, NHC(O)OC2-C6 alkyl, N(C1-C4 alkyl)2, N(C1-C6 alkyl)C(O)OC2-C6 alkyl, OC1-C6 alkyl, OC3-C6 alkenyl, OC3-C6 alkynyl, and OC(O)OC2-C6 alkyl is optionally and independently substituted with one or more independently selected halogen substituents;
• each Group F substituent is selected from the group consisting of halogen, CN, NO2, NH2, NHC1-C6 alkyl, N(C1-C4 alkyl)2, OH, OC1-C6 alkyl, a C3-C6 cycloalkyl, phenyl, and a 5- or 6-membered heteroaryl;
• wherein each NHC1-C6 alkyl, N(C1-C4 alkyl)2, OC1-C6 alkyl, and C3-C6 cycloalkyl is optionally and independently substituted with one or more independently selected halogen substituents;
• and
• wherein each phenyl and 5- or 6-membered heteroaryl is optionally and independently substituted with one or more substituents independently selected from Group D;
• each Group H substituent is selected from the group consisting of halogen, CN, NO2, a C1-C6 hydrocarbon chain, C(O)NH2, C(O)NHC1-C6 alkyl, C(O)C2-C6 alkyl, C(O)N(C1-C4 alkyl)2, C(O)OC2-C6 alkyl, NH2, NHC1-C6 alkyl, NHC(O)OC2-C6 alkyl, N(C1-C4 alkyl)2, N(C1-C6alkyl)C(O)OC2-C6 alkyl, OH, OC1-C6 alkyl, OC(O)OC2-C6 alkyl, a C3-C6 cycloalkyl, phenyl, and a 5- or 6-membered heteroaryl;
• wherein each C1-C6 hydrocarbon chain, C(O)C2-C6 alkyl, C(O)NHC1-C6 alkyl, C(O)N(C1-C4 alkyl)2, C(O)OC2-C6 alkyl, NHC1-C6 alkyl, NHC(O)OC2-C6 alkyl, N(C1-C4 alkyl)2, N(C1-C6 alkyl)C(O)OC2-C6 alkyl, OC1-C6 alkyl, OC(O)OC2-C6 alkyl, and C3-C6 cycloalkyl is optionally and independently substituted with one or more independently selected halogen substituents;
• and
• wherein each phenyl and 5- or 6-membered heteroaryl is optionally and independently substituted with one or more substituents independently selected from Group D;
• and
• each Group J substituent is selected from the group consisting of halogen, CN, a C1-C6 alkyl, C(O)OC2-C6 alkyl, NH2, and OC1-C6 alkyl, wherein each C1-C6 alkyl, C(O)OC2-C6 alkyl, and OC1-C6 alkyl is optionally and independently substituted with one or more independently selected halogen substituents.