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WO 2016/102490 Al 30 June 2016 (30.06.2016) W P O P C T

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WO 2016/102490 Al 30 June 2016 (30.06.2016) W 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 2016/102490 Al 30 June 2016 (30.06.2016) W P O P C T (51) International Patent Classification: (81) Designated States (unless otherwise indicated, for every C07D 333/12 (2006.01) A01N 43/40 (2006.01) kind of national protection available): AE, AG, AL, AM, C07D 405/12 (2006.01) A01N 43/54 (2006.01) AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, C07D 409/12 (2006.01) A01N 43/72 (2006.01) BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, A0 43/10 (2006.01) DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KN, KP, KR, (21) International Application Number: KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, MG, PCT/EP20 15/08083 1 MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, (22) International Filing Date: PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, SC, 2 1 December 2015 (21 .12.2015) 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. (25) Filing Language: English (84) Designated States (unless otherwise indicated, for every (26) Publication Language: English kind of regional protection available): ARIPO (BW, GH, (30) Priority Data: GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, 62/095,077 22 December 2014 (22. 12.2014) US TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, (71) Applicant: BASF SE [DE/DE]; 67056 Ludwigshafen DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, (DE). LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, (72) Inventors: BINDSCHADLER, Pascal; Gartenstr. 34a, GW, KM, ML, MR, NE, SN, TD, TG). 67354 Romerberg (DE). DATTA, Gopal Krishna; Klap- pergasse 11, 60594 Frankfurt (DE). VON DEYN, Published: Wolfgang; An der Bleiche 24, 67435 Neustadt (DE). — with international search report (Art. 21(3)) BRAUN, Franz Josef; 3502 Wild Harvest Ct, Durham, North Carolina 27712 (US). (74) Agent: REITSTOTTER - KINZEBACH; Im Zollhof 1, 6706 1 Ludwigshafen (DE). (54) Title: CYCLIC COMPOUNDS SUBSTITUTED BY A CONDENSED RING SYSTEM (I) o o (57) Abstract: The present invention relates to compounds of formula (I) wherein the variables are as defined in the claims and the o description. The invention further relates to the use of these compounds for controlling invertebrate pests and to plant propagation material and to an agricultural and a veterinary composition comprising said compounds. The invention also relates to novel com pounds useful as intermediate compounds in the preparation of compounds (I). Cyclic compounds substituted by a condensed ring system Description The present invention relates to cyclic compounds substituted by a condensed ring system which are useful for combating or controlling invertebrate pests, in particu lar arthropod pests and nematodes. The invention also relates to a method for control ling invertebrate pests by using these compounds and to plant propagation material and to an agricultural and a veterinary composition comprising said compounds. Invertebrate pests and in particular arthropods and nematodes destroy growing and harvested crops and attack wooden dwelling and commercial structures, causing large economic loss to the food supply and to property. While a large number of pesti cidal agents are known, due to the ability of target pests to develop resistance to said agents, there is an on-going need for new agents for combating invertebrate pests, in particular insects, arachnids and nematodes. Related compounds are described in WO201 1/101229, WO20 13/026724, WO201 3/026726, WO20 14/072480 andEP-A-1731512. However, these documents do not describe compounds having the characteristic substituents and substituents' a r rangement as claimed in the present invention. It is an object of the present invention to provide compounds that have a good pesticidal activity, in particular insecticidal activity, and show a broad activity spectrum against a large number of different invertebrate pests, especially against difficult to con trol arthropod pests and/or nematodes. The object of the present invention is moreover to provide compounds which are less persistent, bioaccumulative and/or toxic than the compounds of the prior art. Es pecially isoxazoline insecticides of the prior art show a high persistency in the soil and thus accumulate there. It has been found that these objectives can be achieved by the compounds of the formula I below, by their stereoisomers, their N-oxides and by their salts, in particular their agriculturally or veterinarily acceptable salts. Therefore, in a first as the formula I (I) wherein X1 is S, O or C ; A is a group A 1 or A 2; wherein is a group of following formula: wherein # denotes the bond to the aromatic ring of formula (I); and W is selected from O and S; and A 2 is a group -C(R7 )(R7b)-N(R )-C(=0)-R 62 B , B2, B3, B4 and B5 are independently selected from the group consisting of N and CR2, with the proviso that at most one of B , B2, B3, B4 and B5 is N; 2 R and R form together a bridging group selected from -CH2CH2CH2-, -CH2CH2CH2CH2-, -CH2CH2O-, -OCH2CH2-, -CH2OCH2-, -OCH2O-, -CH 2C H2S(0)p-, - S(0) PC H2C H2-, -CH 2S(0) PC H2-, -S(0) PC H2S(0) P-, -OCH 2S(0) P -S(0) PCH20-, -OCH2CH2CH2-, -CH2CH2CH2O-, -CH2OCH2CH2-, -CH2CH2OCH2-, -OCH2CH2O-, -OCH2OCH2-, -CH2OCH2O-, -S(0) PCH2CH2CH2-, -CH2CH2CH2S(0) P-, -CH2S(0) PCH2CH2-, -CH2CH2S(0) PCH2-, -S(0) CH2CH2S(0) -, -S(0) CH2S(0) CH2-, -CH2S(0) CH2S(0) -, -S(0) PCH2CH20-, -OCH 2CH2S(0) P-, -S(0) PCH2OCH 2-, -OCH 2S(0) PCH2-, -CH2OCH2S(0) P- and -CH2S(0) PCH20-; where p is 0 , 1 or 2 where the hydrogen atoms of the above groups may be replaced by one or more substituents selected from halogen, methyl, halogenated methyl, hydroxyl, meth oxy and halogenated methoxy; and/or one or two CH2 groups of the above groups may be replaced by a C=0 group; R is d-haloalkyl; each R2 is independently selected from the group consisting of hydrogen, halogen, Ci-C2-haloalkoxy and Ci-C2-haloalkyl; R a and R , independently of each other, are selected from hydrogen and halogen; R7a and R7 , independently of each other, are selected from hydrogen, cyano, methyl and C i-haloalkyl; R5 and R52, independently of each other, are selected from the group consisting of hydrogen, C i-C3 -alkyl, C 2-C3 -alkenyl, C 2-C3 -alkynyl, C i-C6 -alkoxymethyl and is selected from the group consisting of hydrogen, C i-C6 -alkyl, C i-C6 -haloalkyl, C i-C6 -alkyl which carries one or two radicals R8 , C i-C6 -haloalkyl which carries one radical R8 , C 2-C6 -alkenyl, C 2-C6 -haloalkenyl, C 2-C6 -alkynyl, C3-C6 -cycloalkyl which may be substituted by 1 or 2 CN substituents ; C3-C6 -halocycloalkyl; -N(R 0 )R 0 , -CH=NOR 9 1 , phenyl which may be substituted with 1, 2 , 3 , 4 , or 5 substituents R 6 , and a heterocyclic ring selected from rings E-1 to E-63 E-1 E-2 E-3 E-4 E-5 E-6 E-1 E-8 E-9 E-1 0 E-1 1 E-1 2 E-1 3 E-14 E- 5 E-1 6 E-1 7 E-1 8 E-1 9 E-60 E-61 E-62 E-63 where in rings E-1 to E-63 the zigzag line denotes the attachment point to the remainder of the molecule; k is 0 , 1, 2 or 3 ; n is 0, 1 or 2 ; and R 6 is as defined below; R62 is selected from the group consisting of hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkyl substituted by one or two radicals R82, Ci-C6-haloalkyl which carries one radical R82, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6- haloalkynyl,C3-C6-cycloalkyl which optionally carries a CN substituent, C3-C6- halocycloalkyl, -N(R 0 )R 0 b, -C(=0)N(R )R b, -CH=NOR 92, phenyl which is optionally substituted with 1, 2 , 3 , 4 or 5 substituents R 6 ; and a heterocyclic ring selected from rings of formulae E-1 to E-63 as defined above; each R8 is independently selected from OH, CN, Cs-Cs-cycloalkyl which optionally carries a CN or Ci-haloalkyl substituent, C3-C6-halocycloalkyl, Ci-C6-alkoxy, Ci- C 6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfinyl, C1-C6- 0 0 d haloalkylsulfinyl, Ci-C 6-alkylsulfonyl, Ci-C 6-haloalkylsulfonyl, -C(=O)N(R )R , phenyl, optionally substituted with 1, 2 , 3, 4 or 5 substituents R 6 , and a heterocy¬ clic ring selected from rings E-1 to E-63 as defined above; each R82 is independently selected from OH, CN, C3-C6-cycloalkyl which optionally carries a CN or Ci-haloalkyl substituent, C3-C6-halocycloalkyl, Ci-C6-alkoxy, Ci- C 6-haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfinyl, C1-C6- 0 0 d haloalkylsulfinyl, Ci-C 6-alkylsulfonyl, Ci-C 6-haloalkylsulfonyl, -C(=O)N(R )R , phenyl, optionally substituted with 1, 2 , 3 , 4 or 5 substituents R 6 , and a heterocy¬ clic ring selected from rings E-1 to E-63 as defined above; R9 and R92, independently of each other, are selected from hydrogen, Ci-C6-alkyl and d-Ce-haloalkyl; R 0 a , R 02a , R 02 and R 2a , independently of each other, are selected from hydrogen and Ci-C6-alkyl; is selected from hydrogen, -C(=0)N(R 4a)R 4 , phenyl, optionally substituted with 1, 2 , 3 , 4 or 5 substituents R 6 ; and a heterocyclic ring selected from rings of for mulae E-1 to E-42 as defined above; is selected from hydrogen, C i-C6 -alkyl, C i-C6 -haloalkyl, C -CN, C 2-C4 -alkenyl, C 2-C4 -alkynyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C3-C6-cycloalkylmethyl, Cs- C e-halocycloalkylmethyl, phenyl, optionally substituted with 1, 2 , 3, 4 or 5 substituents R 6 ; and a heterocyclic ring selected from rings of formulae
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