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WO 2015/000715 Al 8 January 2015 (08.01.2015) P O P C T

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WO 2015/000715 Al 8 January 2015 (08.01.2015) P O P C T (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 2015/000715 Al 8 January 2015 (08.01.2015) P O P C T (51) International Patent Classification: (30) Priority Data: C07D 471/04 (2006.01) C07D 487/04 (2006.01) 13 174698.4 2 July 201 3 (02.07.2013) EP C07D 471/12 (2006.01) C07D 498/04 (2006.01) 13 176263.5 12 July 201 3 (12.07.2013) EP 13 197069. 1 13 December 2013 (13. 12.2013) EP (21) International Application Number: PCT/CN2014/076736 4 May 2014 (04.05.2014) CN PCT/EP2014/062946 (71) Applicant: SYNGENTA PARTICIPATIONS AG (22) International Filing Date: [CH/CH]; Schwarzwaldallee 215, CH-4058 Basel (CH). 19 June 2014 (19.06.2014) (72) Inventors: EDMUNDS, Andrew; Syngenta Crop Protec (25) Filing Language: English tion Munchwilen AG, Schaffhauserstrasse, CH-4332 Stein (26) Publication Language: English (CH). MUEHLEBACH, Michel; Syngenta Crop Protec tion, Munchwilen AG, Schaffhauserstrasse, CH-4332 Stein (CH). STOLLER, Andre; Syngenta Crop Protection Munchwilen AG, Schaffhauserstrasse, CH-4332 Stein (CH). LOISELEUR, Olivier; Syngenta Crop Protection Munchwilen AG, Schaffhauserstrasse, CH-4332 Stein [Continued on nextpage] (54) Title: PESTICIDALLY ACTIVE BI- OR TRICYCLIC HETEROCYCLES WITH SULFUR CONTAINING SUBSTITUENTS _ _ (57) Abstract: Pesticidally active bi-or tricyclic heterocycles with sulphur-con - a ng substituents, stereoisomers and tautomeric torms thereot that can be used as insecticides and can be prepared in a manner known per se. (CH). BUCHHOLZ, Anke; Syngenta Crop Protection GT, HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KN, Munchwilen AG, Schaffhauserstrasse, CH-4332 Stein KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, (CH). HUETER, Ottmar Franz; Syngenta Crop Protec MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, tion, Munchwilen AG, Schaffhauserstrasse, CH-4332 NI, NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, Stein (CH). BIGOT, Aurelien; Syngenta Crop Protection RU, RW, SA, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, Munchwilen AG, Schaffhauserstrasse, CH-4332 Stein TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, (CH). HALL, Roger Graham; Syngenta Crop Protection VN, ZA, ZM, ZW. Munchwilen AG, Schaffhauserstrasse, CH-4332 Stein (84) Designated States (unless otherwise indicated, for every (CH). EMERY, Daniel; Syngenta Crop Protection AG, kind of regional protection available): ARIPO (BW, GH, Schwarzwaldallee 215, CH-4058 Basel (CH). JUNG, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, SZ, TZ, Marcel; Syngenta Crop Protection, Pierre Joseph UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, Munchwilen AG, Schaffhauserstrasse, CH-4332 Stein TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, (CH). LU, Long; Shanghai Institute of Organic Chem EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, ΓΓ, LT, LU, istry, Chinese Academy of Sciences, No. 345, Lingling LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, Road, Shanghai, 200032 (CN). WU, Yarning; Shanghai SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, Institute of Organic Chemistry, Chinese Academy of Sci GW, KM, ML, MR, NE, SN, TD, TG). ences, No. 345, Lingling Road, Shanghai, 200032 (CN). CHEN, Ruifang; Shanghai Institute of Organic Chem Declarations under Rule 4.17: istry, Chinese Academy of Sciences, No. 345, Lingling — as to applicant's entitlement to apply for and be granted Road, Shanghai, 200032 (CN). a patent (Rule 4.1 7(H)) (74) Agent: SYNGENTA INTERNATIONAL AG; Intellec — of inventorship (Rule 4.17(iv)) tual Property, WRO 1008-Z1-26, Schwarzwaldallee 215, CH-4058 Basel (CH). Published: (81) Designated States (unless otherwise indicated, for every — with international search report (Art. 21(3)) kind of national protection available): AE, AG, AL, AM, — before the expiration of the time limit for amending the AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, claims and to be republished in the event of receipt of BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, amendments (Rule 48.2(h)) DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, Pesticidally active bi- or tricyclic heterocycles with sulfur containing substituents The present invention relates to insecticidally active heterocyclic sulfur containing derivatives, to processes for their preparation, to compositions comprising those compounds, and to their use for controlling animal pests (including arthropods and in particular insects or representatives of the order Acarina). Heterocyclic compounds with pesticidal action are known and described, for example, in WO 2009/131237, WO 201 1/043404, WO 201 1/040629, WO 2010/125985, WO 2012/086848, WO 2013/018928, WO 2013/191 113, WO 2013/180193 and WO 2013/180194. There have now been found novel heterocyclic derivatives with pesticidal properties. The present invention accordingly relates to compounds of formula I, A-B (I), wherein A is a radical selected from the group consisting of formulae A to A8: Ay As wherein the arrow denotes the point of attachment to the radical B; and B is a radical selected from the group consisting of formulae B to B : B3 B B B e Br B Bg Bio Bii wherein the arrow denotes the point of attachment to the radical A ; wherein is methylene or a direct bond; V0 nitrogen or CR5; is CR is CR is CR is CR Vi nitrogen or 20; V2 nitrogen or 2i ; V3 nitrogen or 22; V4 nitrogen or 23; is is CR2 ; is is CR2 ; V5 nitrogen or CR24 ; V6 nitrogen or 5 V7 nitrogen or CR2 6; V8 nitrogen or 7 is is is C R ; V9 nitrogen, or CR2 8 10 nitrogen or CR2 ; V nitrogen or 30 G is nitrogen or C R31; G2 is nitrogen or CR32; G3 is - NR35, an oxygen atom or a sulfur atom; G4 is nitrogen or CR33; is G5 nitrogen or CR34 ; Ji, J2, 3 together form together a 5 membered heterocyclic ring, which can be saturated or unsaturated, containing one or two atoms selected from the group consisting of nitrogen, oxygen and sulfur, which ring can be mono-or polysubstituted by substituents selected from the group consisting of CrC 6alkyl, halogen and or CrC 6haloalkyl, with the proviso that if the ring contains two oxygen atoms, or two sulfur atoms, they are separated by one carbon atom; R and R2 are the same or different and each represents hydrogen, halogen, CrC 6alkyl or d - C6haloalkyl; R3 is a CrC 6alkyl, C2-C6alkenyl or C2-C6alkynyl group which can be mono-or polysubstituted by substituents selected from the group consisting of CrC 6alkoxy, CrC 6haloalkoxy, C2- C6alkenyloxy, C2-C6haloalkenyloxy, C2-C6alkynyloxy, C2-C6haloalkynyloxy, CrC 6alkylsulphanyl, CrC 6haloalkylsulfanyl, CrC 6 alkylsulfinyl, CrC 6haloalkylsulfinyl, CrC 6alkylsulfonyl, d - C6haloalkylsulfonyl, C2-C6alkylcarbonyl, C2-C6haloalkylcarbonyl, C2-C6alkoxycarbonyl, C2- C6haloalkoxycarbonyl, cyano, hydroxy, halogen, C3-C6 cycloalkyi, said C3-C6cycloalkyl itself can be mono- or polysubstituted by substituents selected from halogen and CrC 3alkyl; and by a 5- or 6-membered heterocyclic group, which can be mono- or polysubstituted by substituents selected from the group consisting of CrC 6alkyl, CrC 6haloalkyl, CrC 6alkoxy, CrC 6haloalkoxy, CrC 6alkylsulfanyl, CrC 6haloalkylsulfanyl, CrC 6alkylsulfinyl, CrC 6haloalkylsulfinyl, d - C6alkylsulfonyl, CrC 6haloalkylsulfonyl, C2-C6alkylcarbonyl, C2-C6haloalkylcarbonyl, C2- C6alkoxycarbonyl, C2-C6haloalkoxycarbonyl, Ci-C 6alkylamino, Ci-C 6haloalkylamino, C2- Csdialkylamino, C2-C8halodialkylamino, halogen, cyano and nitro; is or R3 -C0 2R3 6, -C(0)R 3 6 or hydrogen; or R3 is C3-C6cycloalkyl, which can be mono- or polysubstituted by substituents selected from the group consisting of CrC 6alkyl, CrC 6haloalkyl, CrC 6alkoxy, CrC 6haloalkoxy, C2- C6alkenyloxy, C2-C6haloalkenyloxy, C2-C6alkynyloxy, C2-C6haloalkynyloxy and halogen; or R3 is a 5- or 6-membered heterocyclic group, which can be mono- or polysubstituted by substituents selected from the group consisting of CrC 6alkyl, CrC 6haloalkyl, CrC 6alkoxy, d - C6haloalkoxy, CrC 6alkylsulfanyl, CrC 6haloalkylsulfanyl, CrC 6alkylsulfinyl, d - C6haloalkylsulfinyl, CrC 6alkylsulfonyl, CrC 6haloalkylsulfonyl, C2-C6alkylcarbonyl, C2- C6haloalkylcarbonyl, C2-C6alkoxycarbonyl, C2-C6haloalkoxycarbonyl, Ci-C 6alkylamino, C C6haloalkylamino, C2-C8dialkylamino, C2-C8halodialkylamino, halogen, cyano and nitro; R35 is hydrogen, CrC 6alkyl which can be mono- or polysubstituted by substituents selected from the group consisting of CrC 6alkoxy, CrC 6haloalkoxy, C2-C6alkenyloxy, C2-C6haloalkenyloxy, C2-C6 alkynyloxy, C2-C6haloalkynyloxy, CrC 6alkylsulphanyl, CrC 6haloalkylsulfanyl, d - C6alkylsulfinyl, CrC 6haloalkylsulfinyl, CrC 6alkylsulfonyl, CrC 6haloalkylsulfonyl, C2- C6alkylcarbonyl, C2-C6alkoxycarbonyl, cyano, hydroxy, halogen and C3-C6cycloalkyl, said C3- C6cycloalkyl itself can be mono- or polysubstituted by substituents selected from halogen and CrC 3alkyl; or an N-oxide thereof; R4 , R5, R2o, R21 , R22, R23, R 24 , R25, R26, R27, R28, R29 and R3o are the same or different and represents cyano, nitro, halogen, hydroxy, CrC 6alkenyloxy, CrC 6haloalkoxy, -C(0)R 3 6 - C(0)R 3 6 or hydrogen; or CrC 6alkyl which can be mono- or polysubstituted by substitents selected from the group consisting of cyano, halogen, hydroxy, CrC 6alkoxy, CrC 6haloalkoxy, C2-C6alkenyloxy, C2- C6haloalkenyloxy, C2-C6alkynyloxy, C2-C6haloalkynyloxy, CrC 6alkylsulfanyl, d - C6haloalkylsulfanyl, CrC 6alkylsulfinyl, CrC 6haloalkylsulfinyl, CrC 6alkylsulfonyl, d - C6haloalkylsulfonyl, C2-C6alkylcarbonyl, C2-C6haloalkylcarbonyl, C2-C6alkoxycarbonyl, C2- C6haloalkoxycarbonyl, cyano, hydroxy, halogen and C3-C6cycloalkyl,
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