WO 2014/029697 Al 27 February 2014 (27.02.2014) P O P C T
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(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 2014/029697 Al 27 February 2014 (27.02.2014) P O P C T (51) International Patent Classification: (74) Common Representative: BASF SE; 67056 Ludwig A01N 25/00 (2006.01) A01N 43/56 (2006.01) shafen (DE). A0 43/40 (2006.01) A0 43/78 (2006.01) (81) Designated States (unless otherwise indicated, for every A01N 47/24 (2006.01) A0 45/02 (2006.01) kind of national protection available): AE, AG, AL, AM, A01N 43/88 (2006.01) A01P 3/00 (2006.01) AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, A0 37/50 (2006.01) 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 13/067 148 HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, (22) International Filing Date: MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, 16 August 2013 (16.08.2013) OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, (25) Filing Language: English SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, (26) Publication Language: English ZW. (30) Priority Data: (84) Designated States (unless otherwise indicated, for every 1218 13 12.5 22 August 2012 (22.08.2012) EP kind of regional protection available): ARIPO (BW, GH, (71) Applicant: BASF SE [DE/DE]; 67056 Ludwigshafen GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, SZ, TZ, (DE). UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, (72) Inventors: DIACOV, Rogerio Andrade; Rua Borba Gato, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, CEP-04747-030 Sao Paulo (BR). FRATESCHI, Alexan¬ MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, dre; Alameda Pico da Neblina, 350, CEP-06544-440 TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, Santana de Parnaiba/SP (BR). OLIVEIRA, Fabio KM, ML, MR, NE, SN, TD, TG). Eduardo Bueno; Rua Guararapes, CEP-0456 1-004 Sao Paulo (BR). ISMAEL, Marcelo; Avenida das Nacoes Uni- Published: das, n° 14. 171, CEP-04538-132 Rochavera (BR). ZAM- — with international search report (Art. 21(3)) BON, Sergio; Travessa Joao Jose Abdalla, 447, CEP- 13.417-43 1 Piracicaba - SP (BR). o o (54) Title: FUNGICIDAL TERNARY MIXTURES COMPRISING FLUAZINAM (57) Abstract: The present invention relates to fungicidal ternary mixtures comprising at least one inhibitor of complex II and at least one inhibitor of complex III at Q site as defined herein and fluazinam, to composition comprising said mixtures and to the use and to methods for combating phytopathogenic fungi. The present invention also relates to seeds treated with at least one such mix - ture. Furthermore the invention relates to processes for preparing mixtures and compositions of such mixtures. FUNGICIDAL TERNARY MIXTURES COMPRISING FLUAZINAM Description The present invention relates to fungicidal ternary mixtures comprising at least one inhibitor of complex II and at least one inhibitor of complex III at Q0 site as defined herein and fluazinam, to composition comprising said mixtures and to the use and to methods for combating phytopathogenic fungi. The present invention also relates to seeds treated with at least one such mixture. Furthermore the invention relates to processes for preparing mixtures and compositions of such mixtures. Binary mixtures of the inhibitor of complex II boscalid with one of the inhibitors of complex III at Q o site pyraclostrobin, azoxystrobin, fluoxastrobin or trifloxystrobin or with fluazinam have been mentioned in WO 98/08385 and WO 99/31981 , respectively. Further, WO 2007/017416 mentions inter alia binary fungicidal mixtures of the inhibitor of complex II fluxapyroxad with one of the inhibitors of complex III at Q0 site pyraclostrobin, azoxystrobin, fluoxastrobin or trifloxystrobin or with fluazinam. Practical agricultural experience has shown that the repeated and exclusive application of an individual active compound or a binary mixture in the control of harmful fungi leads in many cases to a rapid selection of those fungus strains which have developed natural or adapted resistance against the active compound in question. Effective control of these fungi with the active compound and/or binary mixture in question is then no longer possible. To reduce the risk of the selection of resistant fungus strains, mixtures of more than two different active compounds are employed for controlling harmful fungi. By combining at least three active compounds having different mechanisms of action, it is possible to ensure successful control over a relatively long period of time. It is an object of the present invention to provide, with a view to effective resistance management and effective control of phytopathogenic harmful fungi, at application rates which are as low as possible, compositions which, at a reduced total amount of active compounds applied, have improved activity against the harmful fungi (synergistic mixtures) and a broadened activty spectrum, in particular for certain indications. We have accordingly found that this object is achieved by the mixtures and compositions, defined herein, comprising at least one compound I as defined herein, at least one compound II as defined herein and fluazinam. Moreover, we have found that simultaneous, that is joint or separate, application of a compound I, a compound II and fluazinam or successive application of a compound I, a compound II and fluazinam allows better control of harmful fungi than is possible with the binary mixtures or the individual compounds alone (synergistic mixtures). The invention also relates to a method for controlling phytopathogenic harmful fungi using mixtures of at least one inhibitor of complex II as defined herein and pyraclostrobin and fluazinam and to the use of a compound I and a compound II and fluazinam for preparing such mixtures, and to compositions comprising these mixtures and seed comprising these mixtures or coated with this this mixture. Thus, the present invention relates to mixtures comprising, as active components 1) at least one compound I selected from: fluxapyroxad, boscalid, benzovindiflupyr, bixafen, fluopyram, furametpyr, isopyrazam, penflufen, penthiopyrad, sedaxane, thifluzamide, N-(4'-trifluoromethylthiobiphenyl-2-yl)- 3-difluoromethyl-1 -methyl-1 H-pyrazole-4-carboxamide, N-(2-(1 ,3,3-trimethyl-butyl)- phenyl)-1 ,3-dimethyl-5-fluoro-1 H-pyrazole-4-carboxamide, 3-(difluoromethyl)-1 -methyl- N-(1 , 1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 3-(trifluoromethyl)-1-methyl-N- ( 1 , 1 ,3-trimethylindan-4-yl)pyrazole-4-carboxamide, 1,3-dimethyl-N-(1 , 1 ,3-trimethylindan- 4-yl)pyrazole-4-carboxamide, 3-(trifluoromethyl)-1 ,5-dimethyl-N-(1 , 1 ,3-trimethylindan- 4-yl)pyrazole-4-carboxamide, 3-(difluoromethyl)-1 ,5-dimethyl-N-(1 , 1 ,3-trimethylindan- 4-yl)pyrazole-4-carboxamide and 1,3,5-trimethyl-N-(1 , 1 ,3-trimethylindan-4-yl)pyrazole-4- carboxamide; and 2) at least one compound II selected from: pyraclostrobin, azoxystrobin, fluoxastrobin and trifloxystrobin; and 3) fluazinam. According to one embodiment, these ternary mixtures comprise the component 1), component 2) and component 3) in a synergistically effective amount. In the ternary mixtures according to the invention, i.e. compositions comprising one compound I (component 1) and one compound II (component 2) and fluazinam (component 3), the weight ratio of compound I (component 1) and compound II (component 2) depends from the properties of the active substances used, usually it is in the range of from 1:50 to 50:1 , regularly in the range of from 1:20 to 20:1 , preferably in the range of from 1:10 to 10:1 , more preferably in the range of from 1:4 to 4:1 and in particular in the range of from 1:2 to 2:1 , and the weight ratio of compound I (component 1) and fluazinam (component 3) usually it is in the range of from 1:50 to 50:1 , regularly in the range of from 1:20 to 20:1 , preferably in the range of from 1:10 to 10:1 , more preferably in the range of from 1:4 to 4:1 and in particular in the range of from 1:2 to 2:1 . According to a further embodiment, the weight ratio of component 1) and component 2) is in the range of from 20:1 to 1:20 and the weight ratio of component 1) and component 3) is in the range of from 1: 1 to 1:50. In the ternary mixtures according to the invention, i.e. compositions comprising one compound I selected from boscalid, fluxapyroxad and benzovindiflupyr (as component 1) and one compound II selected from pyraclostrobin and azoxystrobin (component 2) and fluazinam (component 3), the weight ratio of compound I (component 1) and compound II (component 2) depends from the properties of the active substances used, usually it is in the range of from 0.5:1 to 1:5, regularly in the range of from 1: 1 to 1:3, preferably in the range of from 1: 1 .5 to 1:3, and in particular in the range of 1:2, and the weight ratio of compound I (component 1) and fluazinam (component 3) usually it is in the range of from 1: 1 to 1:50, regularly in the range of from 1:5 to 1:25, preferably in the range of from 1:5 to 1:15 and in particular in the range of 1:10.