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(12) STANDARD PATENT (11) Application No. AU 2016337993 B2 (19) AUSTRALIAN PATENT OFFICE

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(12) STANDARD PATENT (11) Application No. AU 2016337993 B2 (19) AUSTRALIAN PATENT OFFICE (12) STANDARD PATENT (11) Application No. AU 2016337993 B2 (19) AUSTRALIAN PATENT OFFICE (54) Title Pyrazine compound and arthropod pest control agent containing same (51) International Patent Classification(s) C07D 241/18 (2006.01) A61K 31/513 (2006.01) A01N 43/60 (2006.01) A61P 33/00 (2006.01) A01P 7/04 (2006.01) C07D 401/04 (2006.01) (21) Application No: 2016337993 (22) Date of Filing: 2016.10.13 (87) WIPO No: W017/065228 (30) Priority Data (31) Number (32) Date (33) Country 2016-149448 2016.07.29 JP 2015-208639 2015.10.23 JP 2015-204376 2015.10.16 JP (43) Publication Date: 2017.04.20 (44) Accepted Journal Date: 2020.10.08 (71) Applicant(s) Sumitomo Chemical Company, Limited (72) Inventor(s) Orimoto, Kohei;Nokura, Yoshihiko;Nakajima, Yuji;Tanabe, Takamasa;Kimura, Takahiro (74) Agent / Attorney Spruson & Ferguson, GPO BOX 3898, Sydney, NSW, 2001, AU (19)~~~10a 0 ,Pi-h . (43) MH %W0 2017 * J 20 (20.04.2017) WO 2017/065228 Al 4 WIPOIPCT (51) MRMHVF3n0: A M $1W±ii 7] RT H2 1 )Kb C07D 241/18 (2006.01) A61K31/513 (2006.01) 2 ±i$1 Hyogo (JP). 1 t4 I (KIMURA, AG1N 43/60 (2006.01) A61P 33/00 (2006.01) Takahiro); T 6658555 iro );6 78 R T H 2 A01P 7/04 (2006.01) C07D 401/04 (2006.01) 1F it ib7?* nRi h Hyogo(JP). (21) [ R9 : PCT/JP2016/080410 (74) ItT¶A:! ' rat (SAMEJIMA,Mutsumietal.); Ts530007t t ilL- T81 (22) [P, R 6t : 2016 P 10 h 13 E (13.10.2016) R E fE 4i (25) [P, A® iB: 841 Osaka(JP). (26) [P, :=3ME 8)t-- (81) tt( ®~iR.±®Ift{ _. f ' ): AE, AG, AL, AM, AO, AT, AU, AZ, BA, (30) 4ittr-9: BB, BG, BH, BN, BR, BW, BY, BZ, CA, CH, CL, CN, 4 1 2015-204376 2015 P 10 h 16 (16.10.2015) JP CO, CR, CU, CZ, DE, DJ, DK, DM, DO, DZ, EC, EE, EG, 4Ji 2015-208639 2015 P 10 h 23 (23.10.2015) JP ES, Fl, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, 4Ji 2016-149448 2016 P 7 h 29 (29.07.2016) JP IN, IR, IS, JP, KE, KG, KN, KP, KR, KW, KZ, LA, LC, (71) , it : K i4L$t $ $TA (SUMITOMO CHEMIC- LK, LR, LS, LU, LY, MA, MD, ME, MG, MK, MN, MW, AL COMPANY, LIMITED) [JP/JP]; T 1048260 JS MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PA, PE, PG, 0 ffrVIlfE* T I 2 7 # 1 F Tokyo (JP). PH, PL, PT, QA, RO, RS, RU, RW, SA, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, (72) 59BEA4: tFT* FI -!(ORIMOTO,Kohei);T6658555 UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. = *MT1 ±$=3]P RT H2 #1 _~ K (84) 0) ®tdZ L , ±r®®6D 6D K ~ihrHyogo (JP).~t Ac-i (NOKURA, Yoshi- i~f= : ARIPO (BW, GH, GM, KE, LR, LS, MW, - hiko ),6555 6658555lid!6 ] T02 1 S4T 66 8i5] Hyogo (JP).tHIT i ~ 'i,NA, RW, SD, SL, ST, SZ, TZ, UG, ZM,ZW), .-L (NAKAIYuiMA66u55;6687 '/ 7 (AM, AZ, BY, KG, KZ, RU, TJ, TM), E - 2ft(I4L, Yujii; Hyogo 66585 / (AL, AT, BE, BG, CH, CY, CZ, DE, DK, EE, PR TE2#1 i t ) ilL(TNABE TA R 68 ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, MC, - (P). mft AS '1(TANABE,Takamasa); T6658555 (54) Title: PYRAZINE COMPOUND AND ARTHROPOD PEST CONTROL AGENT CONTAINING SAME R (57) Abstract: The present invention provides: a compound represented by formula (I) [wherein A' represents a nitrogen atom or 4 4 1 CR ; R represents a hydrogen atom or the like; R represents a C2-C10 linear hydrocarbon group having at least one halogen atom, or the like; R2 represents a Cl-C6 alkyl group which may have at least one halogen atom, or the like; q represents 0, 1, 2 or 3; R3 represents a C1-C6 linear hydrocarbon group which may have at least one halogen atom, or the like; p represents 0, 1, or 2; R rep resents a C1-C6 alkyl group which may have at least one halogen atom, or the like; and n represents 0, 1, or 2] or an N-oxide com Opound thereof; and an arthropod pest control agent which comprises a compound represented by formula (I) and the like and an inert carrier and exhibits an excellent controlling effect against arthropod pests. (57) f [$YT$$] W O 2017/065228 A 1l I |I|I|VII lllI l|||||||||||||I||I|I|I||I|I||||||D||||I||||||||I| MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, hIj-/'1l"t4: TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW' ((J 21 (3)) KM, ML, MR, NE, SN, TD, TG). *59B~qit, TA ( I) [TA*, A'lIt, m"!!!!%TTR It C R 4 - L , R 4 It, 7X*T,9T* - L, R 1 It, 1 10/\mY.M&f C 2 -C 1 OMTMM*7X* -A L, R 2 It, 1 gi4-L0)/ my,>Tq T L-CLT\ tJzl\C1 -C67) 4)X L, qit, 0, 1, 2, R3 AL, R 'It, 1ELL0/\1 L'./NT LT \TiLN\C 1 -C6%2T b7X*E AL , pit, 0, 1, Rit2AL, R 6 it, 1 L®/\DY'./L L CtC1 -C167)-6) JUL, TLT, nit, 0, 1 It22t.o ]T-rLFo71 R It)Nl-/FiL , La t ( I) bi L 1 DESCRIPTION PYRAZINE COMPOUND AND ARTHROPOD PEST CONTROL AGENT CONTAINING SAME 5 TECHNICAL FIELD [0001) This application claims priority to and the benefit of Japanese Patent Application Nos. 2015-204376 filed October 10 16, 2015, 2015-208639 filed October 23, 2015, and 2016 149448 filed July 29, 2016, the entire contents of which are incorporated herein by reference. [0002] The present invention is related to a certain class of 15 pyrazine compound and its use for controlling harmful arthropods. BACKGROUND ART [0003] 20 To date, some compounds for controlling harmful arthropods have been developed and come into practical use. Also, a certain class of compounds has been known to be effective for controlling harmful organisms (see Patent Document 1). 25 2 CITATION LIST PATENT DOCUMENT £00041 Patent Document 1: JP 2000-26421 A 5 SUMMARY OF THE INVENTION (PROBLEMS TO BE SOLVED BY INVENTION) [0005) An object of the present invention is to provide a 10 compound having an excellent efficacy for controlling harmful arthropods. (MEANS TO SOLVE PROBLEMS) [0006] 15 The present invention provides, for example, the following embodiments. [1] A compound represented by formula (I) or its N oxide compound: R2 (O)oS 3 R 1-O N x(R )g (RRG 20 [wherein A represents a nitrogen atom or a CR4 ; 2 R 4 represents a hydrogen atom, a OP2, a NR R, a 3 cyano group, a nitro group, or a halogen atom; R1 represents a C2-C10 chain hydrocarbon group having one or more halogen atoms, a (Cl-C5 alkoxy)C2-C5 alkyl group having one or more halogen atoms, a (Cl-C5 alkylsulfanyl)C2 5 C5 alkyl group having one or more halogen atoms, a (Cl-C5 alkylsulfinyl)C2-C5 alkyl group having one or more halogen atoms, a (Cl-C5 alkylsulfonyl)C2-C5 alkyl group having one or more halogen atoms, a (C3-C7 cycloalkyl)Cl-C3 alkyl group having one or more substituents selected from Group G, or a 10 C3-C7 cycloalkyl group having one or more substituents selected from Group G; R 2 represents a C1-C6 alkyl group optionally having one or more halogen atoms, a cyclopropylmethyl group, or a cyclopropyl group; 15 q represents 0, 1, 2, or 3; R3 represents independently of each other, 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 20 aromatic heterocyclic group optionally having one or more substituents selected from Group D, a OR 2 , a NR"R'2, a NRiiaRi 2 a, a NR 2 9NRlRi 2 , a NR 29OR", a NR"C(O)R 3 , a NR29NR"C(O)R 3 , a NR"lC (0) OR14 , a NR2 9NR"C (0) OR1 4, a NR"lC (0) NR1 5Ris, a NR 24NR"C(0)NR1 5R'6 , a N=CHNR1 5R' 6 , a N=S(0)xR 5R 6, a S(0)yR'5, a 25 C(O)OR1 7, a C(O)NRlRi 2 , a cyano group, a nitro group, or a / n n 1 /I 1 1 \ .nI I 4 halogen atom, and when q is 2 or 3, a plurality of R3 may be identical or different; p represents 0, 1, or 2, R6 represents independently of each other, a C1-C6 alkyl 5 group optionally having one or more halogen atoms, a OR 8 , a NR18R19, a cyano group, a nitro group, or a halogen atom, and when p is 2, a plurality of R6 may be identical or different; 8 R'', R17, R' , R1 9 , R 24 and R2 9 represent independently of each other a hydrogen atom, or a C1-C6 chain hydrocarbon 10 group optionally having one or more halogen atoms; Ri 2 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 23 a S (0) 2 R ; 15 R 2 3 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; Ria and R2a combine together with a nitrogen atom to 20 which they are attached to form a 3 to 7 membered nonaromatic heterocyclic group optionally having one or more substituents selected from Group E {the 3 to 7membered nonaromatic heterocyclic group represents aziridine, azetidine, pyrrolidine, imidazoline, / n n 1 /I 1 1 \ .nI I 5 imidazolidine, piperidine, tetrahydropyrimidine, hexahydropyrimidine, piperazine, azepane, oxazolidine, isooxazolidine, 1,3-oxazinane, morpholine, 1,4-oxazepane, thiazolidine, isothiazolidine, 1,3-thiazinane, 5 thiomorpholine, or 1,4-thiazepane}; R3 represents a hydrogen atom, a Cl-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)Cl-C3 alkyl group 10 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; 15 R" represents a Cl-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)Cl-C3 alkyl group optionally having one or more halogen atoms, or a phenylCl-C3 alkyl 20 group {the phenyl moiety in the phenylCl-C3 alkyl group may optionally have one or more substituents selected from Group D}; 5 R' and R represent independently of each other, a Cl-C6 alkyl group optionally having one or more halogen 25 atoms;
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