(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 2017/016883 Al 2 February 2017 (02.02.2017) P O P C T (51) International Patent Classification: (81) Designated States (unless otherwise indicated, for every A01N 37/18 (2006.01) C07C 233/65 (2006.01) kind of national protection available): AE, AG, AL, AM, C07C 231/12 (2006.01) AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, (21) International Application Number: DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, PCT/EP20 16/066734 HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KN, KP, KR, (22) International Filing Date: KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, MG, 14 July 2016 (14.07.2016) 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, (25) Filing Language: English SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, (26) Publication Language: English TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (30) Priority Data: (84) Designated States (unless otherwise indicated, for every 62/196,3 16 24 July 2015 (24.07.2015) US kind of regional protection available): ARIPO (BW, GH, 16156568.4 1 February 2016 (19.02.2016) EP GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, (71) Applicant: BASF SE [DE/DE]; Carl-Bosch-Strasse 38, TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, 67056 Ludwigshafen am Rhein (DE). DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, (72) Inventors: KOERBER, Karsten; Hintere Lisgewann 26, SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, 69214 Eppelheim (DE). DATTA, Gopal Krishna; Im Ko- GW, KM, ML, MR, NE, SN, TD, TG). erbchen 33, 37079 Goettingen (DE). BINDSCHAEDLER, Pascal; Gartenstr. 34a, 67354 Roemerberg (DE). VON Published: DEYN, Wolfgang; An der Bleiche 24, 67435 Neustadt — with international search report (Art. 21(3)) (DE). BRAUN, Franz-Josef; 3502 Wild Harvest Ct, Durham, 27712 (US). (74) Agent: BASF IP ASSOCIATION; BASF SE, ZRX - 67056 Ludwigshafen (DE). (54) Title: PROCESS FOR PREPARATION OF CYCLOPENTENE COMPOUNDS (I) (ID M x (III) 00 00 (iv) (57) Abstract: The present invention relates to a process for preparing cyclopentene compounds of formula (I) wherein the variables o have the meaning as defined in the description, by cyclisation under basic conditions of a ketone of formula (II) which is obtained by reaction of a compound of formula (III) with a compound of formula (Γν ), novel compounds of formula (I), methods and use of these compounds and combinations for combating invertebrate pests such as insects, arachnids or nematodes in and on plants, and for protecting such plants being infested with pests, and for protecting plant propagation material as like seeds. Process for preparation of cyclopentene compounds Description The present invention relates to a process for preparing cyclopentene compounds of formula I wherein A is a group A , A2 or A3; wherein A1 is: wherein # denotes the attachment point to the remainder of the molecule; W is O, or S ; Y is H, N(R )R6, or OR9 is: wherein # denotes the attachment point to the remainder of the molecule; A3 is a 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heteromonocyclic ring containing 1, 2 , 3 , or 4 heteroatoms N, O, and/or S as ring members, or is a 8-, 9- or 10-membered saturated, partially or fully unsaturated heterobicyclic ring containing 1, 2 , 3, or 4 heteroatoms N, O, and/or S as ring members, which ring may be substituted by one or more same or different R ; B , B2 and B3 are each independently selected from N and CR2, with the proviso that at most two of B , B2, and B3 are N; G , G2, G3 and G4 are each independently selected from N and CR4, with the proviso that at most two of G , G2, G3, and G4 are N; R is Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkoxy-Ci-C4-alkyl, Ci-C4-haloalkoxy -Ci-C4-alkyl-, C 2-C4-alkenyl, C 2-C4-haloalkenyl, C 2-C4-alkynyl, C 2-C4-haloalkynyl, C 3-C6 -cycloalkyl, C3- C -halocycloalkyl, or C(=0)OR 15 ; 2 each R is independently H, halogen, CN, N3, N0 2, SCN, SF5, CrC 6-alkyl, C3-C8-cycloalkyl, C2-C6 -alkenyl, C2-C6 -alkynyl, which groups are unsubstituted, partially or fully halogenated and/or substituted by one or more same or different R8, 9 9 0a 0b Si(R )3, OR , S(0) nR , NR R , phenyl which may be partially or fully substituted by R , and a 3-, 4-, 5-, 6- 7-, 8-, 9- or 10-membered saturated, partially or fully unsaturated heteromonocyclic or heterobicyclic ring containing 1, 2 , 3 or 4 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted, or substituted by one or more same or different R , preferably the unsubstituted or substituted HET; 3a 3b 3 C i C i R , R , R are each independently H, halogen, OH, C0 2R , -C3-alkyl, -C3-haloalkyl, C 2-C3 -alkenyl, C 2-C3 -alkynyl, C i-C3 -alkoxy, C i-C3 -haloalkoxy, C i-C3 -alkylthio, C 1-C3- haloalkylthio, C i-C3 -alkylsulfonyl and C i-C3 -haloalkylsulfonyl; 3a 3b 3e or R and R together form a group =0, =C(R )2, =NOH, or =NOCH3; 3d Ci-Ce C i -Ci R is H, -alkyl, or -C3-alkyloxy -C3-alkyl; each R e is independently H, halogen, CH3, or CF3; each R4 is independently selected from the meanings mentioned for R2, or two R4 bonded to adjacent carbon atoms may form a five- or sixmembered saturated, partially or fully unsaturated carbocyclic ring; each R5 is independently H, CN, Ci-Cio-alkyl , Cs-Cs-cycloalkyl, C2-Cio-alkenyl, C2-Cio-alkynyl, which groups are unsubstituted, partially or fully halogenated and/or 8 9 8 substituted by one or more same or different R , or S(0) nR , or C(=0)R ; each R6 is independently selected from the meanings mentioned for R2; or R5 and R6, together with the nitrogen atom to which they are bound, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated, partially or fully unsaturated heterocyclic ring, which ring may contain 1, 2 , 3 or 4 heteroatoms O, S, N, C=0 and/or C=S as ring members, which heterocyclic ring is unsubstituted or partially or fully substituted by same or different halogen, CN, C i-C6 -alkyl, C i-C6 -haloalkyl, C i-C6 -alkoxy, C i-C6 -haloalkoxy, C i-C6 -alkylthio, C i-C6 -haloalkylthio, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl, C 2-C6 -alkenyl, C 2-C6- haloalkenyl, C 2-C6 -alkynyl, C 2-C6 -haloalkynyl, which groups are unsubstituted, or partially or fully substituted by same or different R8, or phenyl which may be partially or fully substituted by R ; 5 6 0 9 or R and R together form a group =C(R )2, =S(0) m(R )2, =NR , or =NOR ; a R , R are each independently H, halogen, CN, C i-C6 -alkyl, Cs-Cs-cycloalkyl, C 2-C6 -alkenyl, or C 2-C6 -alkynyl, which groups are unsubstituted, partially or fully halogenated and/or substituted by same or different R8; or R a and R4 in position G3 may together form a -ChbCI-b-chain; 8 NO2, Cs-Cs Cs-Cs each R is independently CN, N3, SCN, SF5, -cycloalkyl, -halocycloalkyl, wherein the carbon chains may be substituted by one or more radicals R 3 ; 9 OSO2R 9, 9 0 0 0 0 0 0 Si(R )3, OR , S(0) nR , N(R )R , C(=O)N(R )R , C(=S)N(R )R , C(=0)OR 9, CH=NOR 9, phenyl, which is unsubstituted or partially or fully substituted by same or different R 6 , or a 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heterocyclic ring comprising 1, 2 or 3 heteroatoms N, O, and/or S as ring members, which ring is unsubstituted or partially or fully substituted by same or different R 6 , or two R8 present on the same carbon atom of an alkyl, alkenyl, alkynyl or cycloalkyl group together form a group =0, =C(R )2; =S; =S(0) m(R )2, =S(0) mR N(R )R , =NR , =NOR9; or =NN(R 0 )R 0 ; or two radicals R8, together with the carbon atoms of the alkyl, alkenyl, alkynyl or cycloalkyl group which they are bonded to, form a 3-, 4-, 5-, 6-, 7- or 8-membered saturated or partially unsaturated carbocyclic or heterocyclic ring, which heterocyclic ring comprises 1, 2 , 3 or 4 heteroatoms N, O , and/or S as ring members, and which ring is unsubstituted, or partially or fully substituted by same or different R 6 ; and R8 as a substituent on a cycloalkyi ring may additionally be Ci-C6-alkyl, Ci-C6-haloalkyl, C2-C6- alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, and C2-C6-haloalkynyl, which groups are unsubstituted, or partially or fully substituted by same or different R 3 ; and 8 8 R in the groups C(=0)R and =C(R )2 may additionally be H, halogen, Ci-C 6-alkyl, Ci-Ce- haloalkyI, C2-C6 -alkenyl, C2-C6 -haloalkenyl, C2-C6 -alkynyl, or C2-C6 -haloalkynyl, which groups are unsubstituted, or partially or fully substituted by same or different R 3 ; each R9 is independently H, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, Cs-Cs-cycloalkyl, C3-C8- cycloalkyl-Ci-C4-alkyl-, C 3-Cs-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6- alkynyl, or C2-C6-haloalkynyl, which groups are unsubstituted, or partially or fully substituted by same or different R 3 , or 15 Ci-C 6-alkyl-C(=0)OR , C C6-alkyl-C(=S)N(R )R , Ci-C 6-alkyl-C(=NR )N(R )R , 2 15 13 Si(R )3, S(0) nR , S(0) nN(R )R , N(R )R , N=C(R )2, C(=0)R , C(=0)N(R )R , C(=S)N(R )R , C(=0)OR 15 , or phenyl, which is unsubstituted, or partially or fully substituted by R 6 ; and a 3-, 4-, 5-, 6- or 7-membered saturated, partially or fully unsaturated heterocyclic ring comprising 1, 2 or 3 heteroatoms N, O , and/or S as ring members, which ring is unsubstituted, or partially or fully substituted by same or different R 6 ; and