# US 2014/0194290 A1 · Fused heterocyclic compound and use thereof for pest control > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 2014/0194290 A1 - Document ID: US20140194290A1 - Status: Published application - Kind: A1 - Application number: 14/234,717 - Filed: 2012-08-03 - Published: 2014-07-10 - Earliest claimed: 2011-08-04 - Assignees: Sumitomo Chemical Company, Limited - Inventors: Masaki Takahashi; Takamasa Tanabe; Mai Ito; Yoshihiko Nokura; Atsushi Iwata - Web page: https://patentgrep.com/patent/US20140194290A1 ## CPC - C07D 213/81: Amides; Imides - A01N 43/52: condensed with carbocyclic rings, e.g. benzimidazoles - A01N 43/76: 1,3-Oxazoles; Hydrogenated 1,3-oxazoles - A01N 43/78: 1,3-Thiazoles; Hydrogenated 1,3-thiazoles - A01N 43/90: having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system - A61P 33/14: Ectoparasiticides, e.g. scabicides - C07D 401/04: directly linked by a ring-member-to-ring-member bond - C07D 413/04: directly linked by a ring-member-to-ring-member bond - C07D 417/04: directly linked by a ring-member-to-ring-member bond - C07D 471/04: Ortho-condensed systems - C07D 495/04: Ortho-condensed systems - C07D 498/04: Ortho-condensed systems - C07D 513/04: Ortho-condensed systems - C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08) - A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS - A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS ## Abstract There is provided a compound having an excellent controlling effect on pests represented by the formula (1): wherein, A1 represents —NR7—, etc., A2 represents a nitrogen atom, etc., A3 represents a nitrogen atom, etc., R1 represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X, etc., R2, R3 and R4 are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, etc., R5 and R6 are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X, etc., R7 represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group W, etc., n represents 0, 1 or 2, or an N-oxide thereof. ## Claims ### Claim 1 A compound represented by the formula (1): wherein A1 represents —NR7—, an oxygen atom or a sulfur atom, A2 represents a nitrogen atom or ═CR8—, A3 represents a nitrogen atom or ═CR9—, R1 represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X or a C3-C6 alicyclic hydrocarbon group optionally substituted by one or more atoms or groups selected from Group Y, R2, R3 and R4 are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X, a phenyl group optionally substituted by one or more atoms or groups selected from Group Z, a 5- or 6-membered heterocyclic group optionally substituted by one or more atoms or groups selected from Group Z, —OR10, —S(O)mR10, —S(O)2NR10R11, —NR10R11, —NR10CO2R11, —NR10C(O)R11, —CO2R10, —C(O)R10, —C(O)NR10R11, —SF5, a cyano group, a nitro group, a halogen atom or a hydrogen atom, R5 and R6 are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X, a phenyl group optionally substituted by one or more atoms or groups selected from Group Z, a 5- or 6-membered heterocyclic group optionally substituted by one or more atoms or groups selected from Group Z, —OR10, —S(O)mR10, —S(O)2NR10R11, —NR10R11, —NR10CO2R11, —NR10C(O)R11, —CO2R10, —C(O)R10, —C(O)NR10R11, —SF5, a cyano group, a nitro group, a halogen atom or a hydrogen atom (wherein R5 and R6 do not represents a hydrogen atom at the same time), R7 represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group W, a C1-C6 chain hydrocarbon group substituted by one phenyl group (wherein the phenyl group is optionally substituted by one or more atoms or groups selected from Group Z), a C1-C6 chain hydrocarbon group substituted by one 5- or 6-membered heterocyclic group (wherein the 5- or 6-membered heterocyclic group is optionally substituted by one or more atoms or groups selected from Group Z), —CO2R10, —C(O)R10, a C3-C6 alicyclic hydrocarbon group optionally substituted by one or more atoms or groups selected from Group Y or a hydrogen atom, R8 and R9 are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, —OR10, —S(O)mR10, —NR10R11, —CO2R10, —C(O)R10, a cyano group, a nitro group, a halogen atom or a hydrogen atom, R10 and R11 are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X, a phenyl group optionally substituted by one or more atoms or groups selected from Group Z or a hydrogen atom, each m independently represents 0, 1 or 2, and n represents 0, 1 or 2, wherein the —S(O)mR10, R10 does not a hydrogen atom when m is 1 or 2, Group X: the group consisting of a C1-C6 alkoxy group optionally substituted by one or more halogen atoms, a C2-C6 alkenyloxy group optionally substituted by one or more halogen atoms, a C2-C6 alkynyloxy group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally substituted by one or more halogen atoms, a C2-C6 alkoxycarbonyl group optionally substituted by one or more halogen atoms, a C3-C6 cycloalkyl group optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl groups, a cyano group, a hydroxy group and a halogen atom, Group Y: the group consisting of a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, a C1-C6 alkoxy group optionally substituted by one or more halogen atoms, a C2-C6 alkenyloxy group optionally substituted by one or more halogen atoms, a C2-C6 alkynyloxy group optionally substituted by one or more halogen atoms and a halogen atom, Group Z: the group consisting of a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, a C1-C6 alkoxy group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally substituted by one or more halogen atoms, a C2-C6 alkoxycarbonyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylamino group optionally substituted by one or more halogen atoms, a C2-C8 dialkylamino group optionally substituted by one or more halogen atoms, a halogen atom, a cyano group and a nitro group, Group W: the group consisting of a C1-C6 alkoxy group optionally substituted by one or more halogen atoms, a C2-C6 alkenyloxy group optionally substituted by one or more halogen atoms, a C2-C6 alkynyloxy group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally substituted by one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally substituted by one or more halogen atoms, a C2-C6 alkoxycarbonyl group optionally substituted by one or more halogen atoms, a C3-C6 cycloalkyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally substituted by one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally substituted by one or more halogen atoms, hydroxy group, a halogen atom and a cyano group, or an N-oxide thereof. ### Claim 2 (depends on 1) The compound according to claim 1, wherein A1 is —NR7—, an oxygen atom or a sulfur atom, A2 is a nitrogen atom or ═CR8—, A3 is a nitrogen atom or ═CR9—, R1 is a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X, R2, R3 and R4 are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X, a phenyl group optionally substituted by one or more atoms or groups selected from Group Z, a 5- or 6-membered heterocyclic group optionally substituted by one or more atoms or groups selected from Group Z, —OR10, —S(O)mR10, —SF5, a cyano group, a nitro group, a halogen atom or a hydrogen atom, R5 and R6 are the same or different and each represents a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group X, —OR10, —S(O)mR10, —SF5, a halogen atom or a hydrogen atom, R7 is a C1-C6 chain hydrocarbon group optionally substituted by one or more atoms or groups selected from Group W, a C1-C6 chain hydrocarbon group substituted by one phenyl group (wherein the phenyl group is optionally substituted by one or more atoms or groups selected from Group Z), a C1-C6 chain hydrocarbon group substituted by one 5- or 6-membered heterocyclic group (wherein the 5- or 6-membered heterocyclic group is optionally substituted by one or more atoms or groups selected from Group Z), or a hydrogen atom, R8 is a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, —OR10, —S(O)mR10, a halogen atom or a hydrogen atom, and R9 is a C1-C6 chain hydrocarbon group optionally substituted by one or more halogen atoms, —OR10, —S(O)mR10, a halogen atom or a hydrogen atom. ### Claim 3 (depends on 1) The compound according to claim 1, wherein A1 is —NR7—, an oxygen atom or a sulfur atom, A2 is a nitrogen atom or ═CR8—, A3 is a nitrogen atom or ═CR9—, R1 is a C1-C6 alkyl group optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom and cyclopropyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl group), a C2-C6 alkenyl group optionally substituted by one or more halogen atoms or a C2-C6 alkynyl group optionally substituted by one or more halogen atoms, R2 and R4 are the same or different each other and each represents a halogen atom or a hydrogen atom, R3 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C2-C6 alkenyl group optionally substituted by one or more halogen atoms, a C2-C6 alkynyl group optionally substituted by one or more halogen atoms, 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), —OR10, —S(O)mR10, a cyano group, a nitro group, a halogen atom or a hydrogen atom, R5 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, —OR10, —S(O)mR10, —SF5 or a halogen atom, R6 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, —OR10, —S(O)mR10, a halogen atom or a hydrogen atom, R10 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, R7 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C3-C6 alkenyl group optionally substituted by one or more halogen atoms, a C3-C6 alkynyl group optionally substituted by one or more halogen atoms, a C1-C6 alkyl group substituted by one 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), a hydrogen atom or a C2-C6 alkoxyalkyl group optionally substituted by one or more halogen atoms, R8 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, —OR10, —S(O)mR10, a halogen atom or a hydrogen atom, and R9 is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, —OR10, —S(O)mR10, a halogen atom or a hydrogen atom. ### Claim 4 (depends on 1) The compound according to claim 1, wherein A1 is —NR7—. ### Claim 5 (depends on 1) The compound according to claim 1, wherein A1 is an oxygen atom. ### Claim 6 (depends on 1) The compound according to claim 1, wherein A1 is a sulfur atom. ### Claim 7 (depends on 1) The compound according to claim 1, wherein A2 is ═CR8—. ### Claim 8 (depends on 1) The compound according to claim 1, wherein A2 is ═CR8—, and A3 is a nitrogen atom. ### Claim 9 (depends on 1) The compound according to claim 1, wherein A2 is ═CR8—, A3 is ═CR9—. ### Claim 10 A compound represented by the formula (1-1): wherein A1a represents —NR7a—, an oxygen atom or a sulfur atom, A3a represents a nitrogen atom or ═CR9a—, R1a represents a C1-C6 alkyl group optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom and a cyclopropyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl groups), a C2-C6 alkenyl group optionally substituted by one or more halogen atoms or a C2-C6 alkynyl group optionally substituted by one or more halogen atoms, R2a and R4a are the same or different and each represents a halogen atom or a hydrogen atom, R3a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C2-C6 alkenyl group optionally substituted by one or more halogen atoms, a C2-C6 alkynyl group optionally substituted by one or more halogen atoms, 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), —OR20a (wherein R20a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), —S(O)mR21a (wherein R21a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a cyano group, a nitro group, a halogen atom or a hydrogen atom, R5a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, —OR22a (wherein R22a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), —S(O)mR23a (wherein R23a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), —SF5 or a halogen atom, R7a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C3-C6 alkenyl group optionally substituted by one or more halogen atoms, a C3-C6 alkynyl group optionally substituted by one or more halogen atoms or a C1-C6 alkyl group substituted by one 5- or 6-membered aromatic heterocyclic group, (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), R9a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, —OR24a (wherein R24a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), —S(O)mR25a (wherein R25a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a halogen atom or a hydrogen atom, and n represents 0, 1 or 2, or an N-oxide thereof. ### Claim 11 (depends on 10) The compound according to claim 10, wherein A1a is —NR7a—, an oxygen atom or a sulfur atom, A3a is a nitrogen atom or ═CR9a—, R1a is a C2-C6 alkyl group, a C1-C6 haloalkyl group or C4-C9 cyclopropylalkyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl groups), R2a and R4a both are a hydrogen atom, R3a is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C2-C6 alkenyl group optionally substituted by one or more halogen atoms, a C2-C6 alkynyl group optionally substituted by one or more halogen atoms, pyridyl group (wherein the pyridyl group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), a pyrimidinyl group (wherein the pyrimidinyl group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), —OR20a (wherein R20a is a C1-C6 alkyl group optionally substituted by one or more halogen atoms), —S(O)mR21a(wherein R21a is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, and m is 0, 1 or 2), a halogen atom or a hydrogen atom, R5a is a C1-C6 haloalkyl group, —OR22a (wherein R22a is a C1-C6 haloalkyl group), —S(O)mR23a (wherein R23a is a C1-C6 haloalkyl group, and m is 0, 1 or 2), —SF5 or a halogen atom, and R7a is a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C3-C6 alkenyl group optionally substituted by one or more halogen atoms, a C3-C6 alkynyl group optionally substituted by one or more halogen atoms, a C1-C6 alkyl group substituted by one thiazolyl group (wherein the thiazolyl group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms) or a C1-C6 alkyl group substituted by one pyridyl group (wherein the pyridyl group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms). ### Claim 12 (depends on 10) The compound according to claim 10, wherein A1a is —NR7a—. ### Claim 13 (depends on 10) The compound according to claim 10, wherein A1a is an oxygen atom. ### Claim 14 (depends on 10) The compound according to claim 10, wherein A1a is a sulfur atom. ### Claim 15 A compound represented by the formula (1-2): wherein A3b represents a nitrogen atom or ═CR9b— (wherein R9b represents a hydrogen atom or a halogen atom), R1b represents an ethyl group or a cyclopropylmethyl group, R7b represents methyl group or a propargyl group, R3b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, —OR20b (wherein R20b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), —S(O)mR21b (wherein R21b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a halogen atom or a hydrogen atom, R5b represents a C1-C6 haloalkyl group, —OR22b (wherein R22b represents a C1-C6 haloalkyl group), —S(O)mR23b (wherein R23b represents a C1-C6 haloalkyl group, m represents 0, 1 or 2), —SF5 or a halogen atom, n represents 0, 1 or 2, or an N-oxide thereof. ### Claim 16 A compound represented by the formula (1-3): wherein A3b represents a nitrogen atom or ═CR9b— (wherein R9b represents a hydrogen atom or a halogen atom), R1b represents an ethyl group or a cyclopropylmethyl group, R3b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, —OR20b (wherein R20b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), —S(O)mR21b (wherein R21b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a halogen atom or a hydrogen atom, R5b represents a C1-C6 haloalkyl group, —OR22b (wherein R22b represents a C1-C6 haloalkyl group), —S(O)mR23b (wherein R23b represents a C1-C6 haloalkyl group, m represents 0, 1 or 2), —SF5 or a halogen atom, n represents 0, 1 or 2, or an N-oxide thereof. ### Claim 17 A compound represented by the formula (1-4): wherein A3b represents a nitrogen atom or ═CR9b— (wherein R9b represents a hydrogen atom or a halogen atom), R1b represents an ethyl group or a cyclopropylmethyl group, R3b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, —OR20b (wherein R20b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), —S(O)mR21b (wherein R21b represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a halogen atom or a hydrogen atom, R5b represents, a C1-C6 haloalkyl group, —OR22b (wherein R22b represents a C1-C6 haloalkyl group), —S(O)mR23b (wherein R23b represents a C1-C6 haloalkyl group, m represents 0, 1 or 2), —SF5 or a halogen atom, and n represents 0, 1 or 2, or an N-oxide thereof. ### Claim 18 A compound represented by the formula (1-5): wherein R70a represents hydrogen atom or a C2-C6 alkoxyalkyl group optionally substituted by one or more halogen atoms, A3a represents a nitrogen atom or ═CR9a—, R1a represents a C1-C6 alkyl group optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom and a cyclopropyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl groups), a C2-C6 alkenyl group optionally substituted by one or more halogen atoms or a C2-C6 alkynyl group optionally substituted by one or more halogen atoms, R2a and R4a are the same or different and each represents a halogen atom or a hydrogen atom, R3a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C2-C6 alkenyl group optionally substituted by one or more halogen atoms, a C2-C6 alkynyl group optionally substituted by one or more halogen atoms, 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), —OR20a (wherein R20a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), —S(O)mR21a (wherein R21a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a cyano group, a nitro group, a halogen atom or a hydrogen atom, R5a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, —OR22a (wherein R22a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), —S(O)mR23a (wherein R23a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), —SF5 or a halogen atom, R9a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, —OR24a (wherein R24a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), —S(O)mR25a (wherein R25a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a halogen atom or a hydrogen atom, and n represents 0, 1 or 2, or an N-oxide thereof. ### Claim 19 (depends on 1) A pest control composition comprising a compound according to claim 1 and an inert carrier. ### Claim 20 (depends on 1) A method for controlling a pest, which comprises applying an effective amount of the compound according to claim 1 to the pest or a habitat of the pest. ### Claim 21 A compound represented by the formula (M3-1): wherein A1a represents —NR7a—, an oxygen atom or a sulfur atom, A3a represents a nitrogen atom or ═CR9a—, R1a represents a C1-C6 alkyl group optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom and a cyclopropyl group (wherein the cyclopropyl group is optionally substituted by one or more halogen atoms or one or more C1-C3 alkyl groups), a C2-C6 alkenyl group optionally substituted by one or more halogen atoms or a C2-C6 alkynyl group optionally substituted by one or more halogen atoms, R2a and R4a are the same or different and each represents a halogen atom or a hydrogen atom, R3a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C2-C6 alkenyl group optionally substituted by one or more halogen atoms, a C2-C6 alkynyl group optionally substituted by one or more halogen atoms, 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), —OR20a (wherein R20a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), —S(O)mR21a (wherein R21a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a cyano group, a nitro group, a halogen atom or a hydrogen atom, R5a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, —OR22a (wherein R22a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), —S(O)mR23a (wherein R23a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), —SF5 or a halogen atom, R7a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C3-C6 alkenyl group optionally substituted by one or more halogen atoms, a C3-C6 alkynyl group optionally substituted by one or more halogen atoms, or a C1-C6 alkyl group substituted by one 5- or 6-membered aromatic heterocyclic group, (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), R9a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, —OR24a (wherein R24a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), —S(O)mR25a (wherein R25a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a halogen atom or a hydrogen atom, and n represents 0, 1 or 2, or an N-oxide thereof. ### Claim 22 A compound represented by the formula (M6-1): wherein V2 represents a halogen atom, A1a represents —NR7a—, an oxygen atom or a sulfur atom, A3a represents a nitrogen atom or ═CR9a—, R2a and R4a are the same or different and each represents a halogen atom or a hydrogen atom, R3a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C2-C6 alkenyl group optionally substituted by one or more halogen atoms, a C2-C6 alkynyl group optionally substituted by one or more halogen atoms, 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), —OR20a (wherein R20a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), —S(O)mR21a (wherein R21a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a cyano group, a nitro group, a halogen atom or a hydrogen atom, R5a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, —OR22a (wherein R22a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), —S(O)mR23a (wherein R23a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), —SF5 or a halogen atom, R7a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C3-C6 alkenyl group optionally substituted by one or more halogen atoms, a C3-C6 alkynyl group optionally substituted by one or more halogen atoms, or a C1-C6 alkyl group substituted by one 5- or 6-membered aromatic heterocyclic group, (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), and R9a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, —OR24a (wherein R24a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), —S(O)mR25a (wherein R25a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a halogen atom or a hydrogen atom, or an N-oxide thereof. ### Claim 23 A compound represented by the formula (M20-1): wherein V2 represents a halogen atom, A1a represents —NR7a—, an oxygen atom or a sulfur atom, A3a represents a nitrogen atom or ═CR9a—, R2a and R4a are the same or different and each represents a halogen atom or a hydrogen atom, R3a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C2-C6 alkenyl group optionally substituted by one or more halogen atoms, a C2-C6 alkynyl group optionally substituted by one or more halogen atoms, 5- or 6-membered aromatic heterocyclic group (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), —OR20a (wherein R20a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), —S(O)mR21a (wherein R21a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a cyano group, a nitro group, a halogen atom or a hydrogen atom, R5a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, —OR22a (wherein R22a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), —S(O)mR23a (wherein R23a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), —SF5 or a halogen atom, R7a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, a C3-C6 alkenyl group optionally substituted by one or more halogen atoms, a C3-C6 alkynyl group optionally substituted by one or more halogen atoms, or a C1-C6 alkyl group substituted by one 5- or 6-membered aromatic heterocyclic group, (wherein the 5- or 6-membered aromatic heterocyclic group is optionally substituted by one or more atoms or groups selected from the group consisting of a halogen atom, a C1-C3 alkyl group optionally substituted by one or more halogen atoms, and a C1-C3 alkoxy group optionally substituted by one or more halogen atoms), and R9a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, —OR24a (wherein R24a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms), —S(O)mR25a (wherein R25a represents a C1-C6 alkyl group optionally substituted by one or more halogen atoms, m represents 0, 1 or 2), a halogen atom or a hydrogen atom, or an N-oxide thereof.