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WO 2014/177514 Al 6 November 2014 (06.11.2014) P O P C T

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WO 2014/177514 Al 6 November 2014 (06.11.2014) 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 2014/177514 Al 6 November 2014 (06.11.2014) P O P C T (51) International Patent Classification: (74) Agent: BIP PATENTS; c/o Bayer Intellectual Property A01N 37/28 (2006.01) A01N 43/56 (2006.01) GmbH, Alfred-Nobel-Str. 10, 40789 Monheim am Rhein A01N 43/08 (2006.01) A01N 43/60 (2006.01) (DE). A01N 43/10 (2006.01) C07D 241/24 (2006.01) (81) Designated States (unless otherwise indicated, for every A01N 43/40 (2006.01) A01P 5/00 (2006.01) kind of national protection available): AE, AG, AL, AM, (21) International Application Number: AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, PCT/EP2014/058594 BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, (22) International Filing Date: HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KN, KP, KR, 28 April 2014 (28.04.2014) KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, (25) Filing Language: English MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, (26) Publication Language: English SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, (30) Priority Data: TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, 13 166002.9 30 April 2013 (30.04.2013) EP zw. (71) Applicant: BAYER CROPSCIENCE AG [DE/DE]; Al- (84) Designated States (unless otherwise indicated, for every fred-Nobel-Str. 50, 40789 Monheim (DE). kind of regional protection available): ARIPO (BW, GH, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, SZ, TZ, (72) Inventors: DECOR, Anne; Solinger Strasse 117, 40764 UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, Langenfeld (DE). GREUL, Jorg Nico; Max-Schonenberg- TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, StraBe 64, 51381 Leverkusen (DE). HEILMANN, Eike EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, Kevin; Steinkribbenstr. 9, 40597 Dusseldorf (DE). MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, SCHWARZ, Hans-Georg; Auf dem Beerenkamp 82 b, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, 46282 Dorsten (DE). COQUERON, Pierre-Yves; Rue KM, ML, MR, NE, SN, TD, TG). Masaryk 22, F-69009 Lyon (FR). PORTZ, Daniela; Ost- Declarations under Rule 4.17 : str. 1, 52391 VettweiB (DE). ILG, Kerstin; Neusser Wall 32, 50670 Koln (DE). MALSAM, Olga; Vor dem Kloster- — as to applicant's entitlement to apply for and be granted a hof 19, 51503 Rosrath (DE). LOSEL, Peter; Am Schokker patent (Rule 4.1 7(H)) 5, 51371 Leverkusen (DE). LUMMEN, Peter; Lanaer Str. Published: 76, 655 10 Idstein (DE). GORGENS, Ulrich; Fester Str. 37, 40882 Ratingen (DE). DESBORDES, Philippe; 14 rue — with international search report (Art. 21(3)) du Docteur Mouisset, F-69006 Lyon (FR). (54) Title: NEMATICIDAL N-SUBSTITUTED PHENETHYLCARBOXAMIDES (57) Abstract: The present invention relates to the use of known and novel N-substituted phenethylcarboxamides for the control of nematodes in agriculture and their use as anthelmintics against endoparasites in animals or humans, compositions containing such compounds and methods for the control of nematodes and helminths and further relates to novel to N-substituted phenethylcarbox amides, processes and intermediate compounds for their preparation, their use as nematicides, compositions containing such com pounds and methods for the control of nematodes and helminths. Nematicidal N-substituted phenethylcarboxamides The present invention relates to the use of known and novel N-substituted phenethylcarboxamides for the control of nematodes in agriculture and their use as anthelmintics against endoparasites in animals or humans, compositions containing such compounds and methods for the control of nematodes and helminths. The present invention further relates to novel to N-substituted phenethylcarboxamides, processes and intermediate compounds for their preparation, their use as nematicides, compositions containing such compounds and methods for the control of nematodes and helminths. Nematodes cause a substantial loss in agricultural product including food and industrial crops and are combated with chemical compounds having nematicidal activity. To be useful in agriculture these compounds should have a high activity, a broad spectrum activity against different strains of nematodes and should not be toxic to non-target organisms. The occurrence of resistances against commercially available anthelmintics seems to be a growing problem in the area of veterinary medicine. Therefore, endoparasiticides with new molecular modes of actions are urgently desired. The new active ingredients should perform with excellent efficacy against a broad spectrum of helminths and nematodes without any adverse toxic effects to the treated animal. Endoparasiticides are pharmaceuticals for combat or suppression of endoparasites in animals or humans. In WO 201 1/147690 Al certain fungicidal pyrazole carboxamide derivatives are generically embraced in a broad disclosure of numerous compounds of the following formula: wherein n can be 0 and R can represent hydrogen, C -C -alkyl or C -C -haloalkyl. However, this document is silent about a nematicidal efficacy of the disclosed compounds. In WO 201 0/063700 A2 certain fungicidal pyrazole carboxamide derivatives are generically embraced in a broad disclosure of numerous compounds of the following formula: wherein X can represent a direct bond, an oxygen atom or a sulfur atom and wherein n can be 0, R can represent hydrogen, C -C -alkyl or C -C -haloalkyl and R7 can represent hydrogen, halogen, C -C -alkyl, C2-C6 -alkenyl, C3-C6 -alkynyl. However, this document is silent about a nematicidal efficacy of the disclosed compounds. Pyridinecarboxylic acid derivatives which are useful in treating a viral disease are disclosed in US 201 3/01 02600. Modern crop protection compositions have to meet many demands, for example in relation to the level, duration and breadth of their action and possible use. Questions of toxicity and of combinability with other active ingredients or formulation auxiliaries play a role, as does the question of the expense that the synthesis of an active ingredient requires. In addition, resistances can occur. For all these reasons, the search for novel crop protection compositions cannot be considered to be complete, and there is a constant need for novel compounds having properties which, compared to the known compounds, are improved at least in relation to individual aspects. It was an object of the present invention to provide compounds which widen the spectrum of the pesticides in various respects. This object, and further objects which are not stated explicitly but can be discerned or derived from the connections discussed herein, are achieved by the use of compounds of formula (I) (I) wherein A represents phenyl of formula A (A ) wherein * indicates the bond which connects A to the C=0 moiety of the compounds of formula (I), 1 Y represents halogen, nitro, SH, SF5, CHO, OCHO, NHCHO, cyano, Ci-Cg-alkyl, Ci-Cg-halogenoalkyl having 1 to 5 halogen atoms, C2-Cg-alkenyl, C2-Cg-alkynyl, C3-C6 -cycloalkyl, C3-C6 -halogenocycloalkyl having 1 to 9 halogen atoms, Ci-Cg-alkylsulfanyl, -Ci-Cg -halogenoalkylsulfanyl having 1 to 5 halogen atoms, Ci-Cg-alkoxy, Ci-Cg -halogenoalkoxy having 1 to 5 halogen atoms, Ci-Cg -alkoxy-Ci-Cg -alkyl, C2- C g-alkenyloxy-Ci-Cg -alkyl, C 3-Cg-alkynyloxy-Ci-Cg -alkyl, C2-Cg-alkenyloxy, C 3-Cg-alkynyloxy, Ci-Cg- alkoxycarbonyl, Ci-Cg-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, Ci-Cg-alkylcarbonyloxy, Ci-Cg-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, Ci-Cg-alkylsulfinyl, Ci-Cg- halogenoalkylsulfinyl having 1 to 5 halogen atoms, Ci-Cg-alkylsulfonyl, Ci-Cg-halogenoalkylsulfonyl having 1 to 5 halogen atoms, Ci-Cg-alkylsulfonamide, substituted or unsubstituted tri-(Ci-Cg )-alkylsilyl, substituted or unsubstituted aryl and substituted or unsubstituted aryloxy; Y2, Y3, Y4 and Y5 independently from each other represent hydrogen or Y1; or A represents a carbo-linked heterocyclyl group optionally substituted by 1 to five groups R, wherein R independently from each other R represents hydrogen, halogen, nitro, cyano, hydroxy, amino, sulfanyl, pentafluoro^ -sulfanyl, substituted or unsubstituted (Ci-Cg -alkoxyimino)-Ci-Cg -alkyl, substituted or unsubstituted (benzyloxyimino)-Ci-Cg -alkyl, substituted or unsubstituted Ci-Cg-alkyl, Ci-Cg- halogenoalkyl having 1 to 5 halogen atoms, substituted or unsubstituted C2-Cg-alkenyl, C2-Cg- halogenoalkenyl having 1 to 5 halogen atoms, substituted or unsubstituted C2-Cg-alkynyl, C2-Cg- halogenoalkynyl having 1 to 5 halogen atoms, substituted or unsubstituted Ci-Cg -alkoxy, Ci-Cg- halogenoalkoxy having 1 to 5 halogen atoms, substituted or unsubstituted Ci-Cg -alkylsulfanyl, Ci-Cg- halogenoalkylsulfanyl having 1 to 5 halogen atoms, substituted or unsubstituted Ci-Cg -alkylsulfinyl, Ci- C g-halogenoalkylsulfinyl having 1 to 5 halogen atoms, substituted or unsubstituted Ci-Cg -alkylsulfonyl, Ci-C8 -halogenoalkylsulfonyl having 1 to 5 halogen atoms, substituted or unsubstituted Ci-Cs -alkylamino, substituted or unsubstituted di-Ci-Cs-alkylamino, substituted or unsubstituted C2-C8 -alkenyloxy, substituted or unsubstituted C3-C8 -alkynyloxy, substituted or unsubstituted C3-C7 -cycloalkyl, C3-C7- halogenocycloalkyl having 1 to 5 halogen atoms, substituted or unsubstituted tri-(Ci-C8-alkyl)-silyl, substituted or unsubstituted Ci-Cs -alkylcarbonyl, Ci-Cs -halogenoalkylcarbonyl
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