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WO 2017/213252 Al 14 December 2017 (14.12.2017) W !P O PCT

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WO 2017/213252 Al 14 December 2017 (14.12.2017) W !P O PCT (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date WO 2017/213252 Al 14 December 2017 (14.12.2017) W !P O PCT (51) International Patent Classification: TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, C07D 413/04 (2006.01) C07D 271/07 (2006.01) EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, C07D 417/10 (2006.01) A01N 43/836 (2006.01) MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, (21) International Application Number: KM, ML, MR, NE, SN, TD, TG). PCT/JP20 17/02 1473 (22) International Filing Date: Published: 09 June 2017 (09.06.2017) — with international search report (Art. 21(3)) (25) Filing Language: English (26) Publication Language: English (30) Priority Data: 2016-1 15977 10 June 2016 (10.06.2016) 2016-239161 09 December 2016 (09.12.2016) (71) Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED [JP/JP]; 27-1, Shinkawa 2-chome, Chuo-ku, Tokyo, 1048260 (JP). (72) Inventors: ARIMORI, Sadayuki; c/o SUMITOMO CHEMICAL COMPANY, LIMITED, 2-1, Takatsukasa 4-chome, Takarazuka-shi, Hyogo, 6658555 (JP). YA- MAMOTO, Masaoki; c/o SUMITOMO CHEMICAL COMPANY, LIMITED, 2-1, Takatsukasa 4-chome, Takarazuka-shi, Hyogo, 6658555 (JP). (74) Agent: SAMEJIMA, Mutsumi et al; AOYAMA & PARTNERS, Umeda Hankyu Bldg. Office Tower, 8-1, Kakuda-cho, Kita-ku, Osaka-shi, Osaka, 5300017 (JP). (81) Designated States (unless otherwise indicated, for every kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DJ, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IR, IS, JO, JP, KE, KG, KH, KN, KP, KR, KW, KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (84) Designated States (unless otherwise indicated, for every kind of regional protection available): ARIPO (BW, GH, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, (54) Title: OXADIAZOLE COMPOUND AND USE AS PESTICIDE H H (57) Abstract: The present invention provides a compound having excellent control efficacies against pests. Specifically, the present invention provides a compound rep- N. ( I ) resented by formula (I): (wherein: A is a single bond, etc.; m is any one integer of 0 to O N 3; X is a single bond, a CR4R5, a NR6, or an oxygen atom; R2, R3, R4, and R5 are in dependently of each other a hydrogen atom, etc.; R6 is a hydrogen atom, etc.; n is 0, 1, F 3 7 7 or 2; Q is an oxygen atom, a NR , a N-CN, a N-NO2, etc.; R is a hydrogen atom, etc.; o G is a benzene ring, etc.; Y is a CR R R1 , etc.; and R8, R9, and R1 are independently of each other a hydrogen atom, etc.) having excellent control efficacies against pests. Description Title of Invention: OXADIAZOLE COMPOUND AND USE AS PESTICIDE Technical Field [0001] This application claims priorities to and the benefits of Japanese Patent Application Nos. 2016-115977 filed on June 10, 2016 and 2016-239161 filed on December 9, 2016, the entire contents of which are incorporated herein by reference. The present invention relates to an oxadiazole compound and use thereof. Background Art [0002] Patent Literature 1 discloses some compounds such as a compound represented by the following formula for medical use. [Chem.l] Citation List Patent Literature [0003] PTL 1: WO 2013/008 162 pamphlet Summary of Invention Technical Problem [0004] An object of the present invention is to provide a compound having excellent control efficacies against pests. Solution to Problem [0005] The present inventors have intensively studied to find out a compound having excellent control efficacies against pests. As a result, they have found out that a compound represented by the following formula (I) has excellent control efficacies against pests. That is, the present invention provides the followings: [1] A compound represented by formula (I): [Chem.2] [wherein: A is a single bond, a NR1, or an oxygen atom; m is any one integer of 0 to 3; R1 is a C1-C6 alkyl group optionally having one or more halogen atoms, or a hydrogen atom; X is a single bond, a CR4R5, a NR6, or an oxygen atom; R2, R3, R4, and R5 are independently of each other a C1-C6 alkyl group optionally having one or more substituents selected from Group A, a C1-C6 alkoxy group op tionally having one or more substituents selected from Group B, a phenyl group op tionally having one or more substituents selected from Group D, a pyridyl group op tionally having one or more substituents selected from Group D, a C3-C6 cycloalkyl group optionally having one or more substituents selected from Group D, a hydrogen atom, a halogen atom, or a cyano group, or R2 and R3 may be combined with the carbon atom to which they are attached to form a 3 to 6 membered ring (wherein said 3 to 6 membered ring may optionally have one or more substituents selected from Group D), wherein when m is 2 or 3, two or more R2 and R3 may be identical or different; R6 is a C1-C6 alkyl group optionally having one or more substituents selected from Group A, a C3-C6 alkenyl group optionally having one or more halogen atoms, a C3-C6 alkynyl group optionally having one or more halogen atoms, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C3-C6 cycloalkyl group op tionally having one or more substituents selected from Group D, a phenyl group op tionally having one or more substituents selected from Group D, a 5 membered aromatic heterocyclic group optionally having one or more substituents selected from Group D, a 6 membered aromatic heterocyclic group optionally having one or more substituents selected from Group D, or a hydrogen atom; n is 0, 1, or 2; 7 7 7 Q is an oxygen atom, a NR , a N-CN, a N-N0 2, a N-C(0)R , a N-C(0)OR , or a N- 7 S(0) 2R (wherein when n is 2, two Q may be identical or different); R7 is a C1-C6 alkyl group optionally having one or more substituents selected from the group consisting of a halogen atom and a cyano group, or a hydrogen atom; G is a thiophene ring, a furan ring, an imidazole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an oxadiazole ring, a thiadiazole ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, or a benzene ring {wherein said thiophene ring, said furan ring, said imidazole ring, said oxazole ring, said isoxazole ring, said thiazole ring, said pyridine ring, said pyrazine ring, said pyridazine ring, and said pyrimidine ring may optionally have one or more substituents selected from Group D, and when n is 0, said benzene ring may optionally have one or more substituents selected from Group I, and when n is 1 or 2, said benzene ring may optionally have one or more substituents selected from Group D}; Y is a C3-C6 cycloalkyl group optionally having one or more substituents selected from Group D, a phenyl group optionally having one or more substituents selected from Group D, a 5 membered aromatic heterocyclic group optionally having one or more substituents selected from Group D, a 6 membered aromatic heterocyclic group optionally having one or more substituents selected from Group G, a 3 to 6 membered nonaromatic heterocyclic group optionally having one or more substituents selected from Group D , a CR R R 10 , a NR R12 , or a OR 13 ; R8, R , and R10 are independently of each other a C1-C6 alkyl group optionally having one or more substituents selected from the group consisting of Group A and Group F, a C3-C6 alkenyl group optionally having one or more halogen atoms, a C3-C6 alkynyl group optionally having one or more halogen atoms, a C1-C6 alkoxy group optionally having one or more substituents selected from Group B, a C3-C6 cycloalkyl group op tionally having one or more substituents selected from Group D, a phenyl group op tionally having one or more substituents selected from Group D, a 5 to 6 membered aromatic heterocyclic group optionally having one or more substituents selected from Group D, a hydrogen atom, a halogen atom, or a cyano group; R 1 1 and R12 are independently of each other a C1-C6 alkyl group optionally having one or more substituents selected from the group consisting of Group E and Group F, a C3-C6 alkenyl group optionally having one or more halogen atoms, a C3-C6 alkynyl group optionally having one or more halogen atoms, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C3-C6 cycloalkyl group optionally having one or more substituents selected from Group D, a phenyl group optionally having one or more substituents selected from Group D, a 5 to 6 membered aromatic heterocyclic group optionally having one or more substituents selected from Group D, or a hydrogen atom, or R 1 1 and R 12 may be combined with each other to form a 3 to 8 membered heterocyclic group (wherein said 3 to 8 membered heterocyclic group may optionally have one or more substituents selected from Group D); and R 13 is a C1-C6 alkyl group optionally having one or more substituents selected from the group consisting of Group A and Group F, a C3-C6 alkenyl group optionally having one or more halogen atoms, a C3-C6 alkynyl group optionally having one or more halogen atoms, a C3-C6 cycloalkyl group optionally having one or more sub- stituents selected
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