(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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