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Fungicidal Mixtures (19) TZZ¥¥Z___T (11) EP 3 530 118 A1 (12) EUROPEAN PATENT APPLICATION (43) Date of publication: (51) Int Cl.: 28.08.2019 Bulletin 2019/35 A01P 3/00 (2006.01) A01N 43/40 (2006.01) A01N 43/56 (2006.01) (21) Application number: 18158566.2 (22) Date of filing: 26.02.2018 (84) Designated Contracting States: (72) Inventors: AL AT BE BG CH CY CZ DE DK EE ES FI FR GB • SANTOS, Paulo Sergio Jose Dos GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO 67117 Limburgerhof (DE) PL PT RO RS SE SI SK SM TR • GEWEHR, Markus Designated Extension States: 67117 Limburgerhof (DE) BA ME • VONEND, Michael Designated Validation States: 67056 Ludwigshafen (DE) MA MD TN (74) Representative: BASF IP Association (71) Applicant: BASF SE BASF SE 67056 Ludwigshafen am Rhein (DE) G-FLP-C006 67056 Ludwigshafen (DE) (54) FUNGICIDAL MIXTURES (57) The present invention relates to fungicidal mixtures comprising, as active components, Fluxapy-roxad (I) and Florylpicoxamid (II), and optionally a third fungicidal compound III, wherein compound III is selected from groups (A) to (E), as well as methods to combat phytopathogenic fungi based on such mixtures. EP 3 530 118 A1 Printed by Jouve, 75001 PARIS (FR) 1 EP 3 530 118 A1 2 Description tetralin-1-yl-pyridine-2-carboxamide, 4-[1-[2-[3-(difluoromethyl)-5-(trifluorome- [0001] The present invention relates to fungicidal mix- thyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin- tures comprising, as active components, Fluxapyroxad 1-yl-pyridine-2-carboxamide, 4-[1-[2-[5-cyclo- (I) and Florylpicoxamid (II), and optionally a third fungi- 5 propyl-3-(difluoromethyl)pyrazol-1-yl]acetyl]-4- cidal compound III, wherein compound III is selected from piperidyl]-N-tetralin-1-yl-pyridine-2-carboxam- groups (A) to (E) consisting of: ide, 4-[1-[2-[5-methyl-3-(trifluoromethyl)pyra- zol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyri- A) Respiration inhibitors dine-2-carboxamide, 4-[1-[2-[5-(difluorome- 10 thyl)-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4- - Inhibitors of complex III at Q o site: azoxystrobin, piperidyl]-N-tetralin-1-yl-pyridine-2-carboxam- dimoxystrobin, kresoxim-methyl, picoxystrobin, ide, 4-[1-[2-[3,5-bis(trifluoromethyl)pyrazol-1- pyraclostrobin, trifloxystrobin, famoxadone; yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2- carboxamide, (4-[1-[2-[5-cyclopropyl-3-(trifluor- 15 - inhibitors of complex III at Qi site: cyazofamid; omethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-te- tralin-1-yl-pyridine-2-carboxamide; - inhibitors of complex II: bixafen, boscalid, fluopyram, penthiopyrad, pydiflumetofen, inpyr- D) Inhibitors with Multi Site Action: mancozeb, me- fluxam isoflucypram, 2-(difluorome-tiram, zineb, chlorothalonil, folpet, dithianon; thyl)-N-(1,1,3-trimethyl-indan-4-yl)pyridine-3- 20 carboxamide, 2-(difluoromethyl)-N-[(3R)-1,1,3- E) Other fungicides: fosetyl, fosetyl-aluminum; met- trimethylindan-4-yl]pyridine-3-carboxamide, alaxyl, metalaxyl-M, carbendazim, thiophanate-me- 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-in- thyl, fluopicolide, metrafenone, pyrimethanil; fludiox- dan-4-yl)pyridine-3-carboxamide, 2-(difluor- onil; quinoxyfen; cymoxanil, proquinazid,N’-(4-(4- omethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4- 25 chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl- yl]pyridine-3-carboxamide,2-(difluorome- phenyl)-N-ethyl-N-methyl formamidine, N’-(4-(4- thyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyrid- fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethylphe- ine-3-carboxamide, 2-(difluoromethyl)-N-[(3R)- nyl)-N-ethyl-N-methyl formamidine, picarbutrazox, 1,1-dimethyl-3-propyl-indan-4-yl]pyridine-3- pentyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl- carboxamide, 2-(difluoromethyl)-N-(3-isobutyl- 30 methylene]amino]oxymethyl]-2-pyridyl]carbamate, 1,1-dimethyl-indan-4-yl)pyridine-3-carboxam- but-3-ynyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl- ide, 2-(difluoromethyl)-N-[(3R)-3-isobutyl-1,1- methylene]amino]oxymethyl]-2-pyridyl]carbamate. dimethyl-indan-4-yl]pyridine-3-carboxamide; [0002] Moreover, the invention relates to a method for - other respiration inhibitors: fluazinam, meptyldi- 35 controlling phytopathogenic fungi, using the inventive nocap, ametoctradin; mixtures of compounds I, II and optionally III, and to the use of compounds I, II and optionally a compound III as B) Sterol biosynthesis inhibitors (SBI fungicides): defined abovefor preparing such mixtures, and also com- difenoconazole, epoxiconazole, fluquinconazole, positions comprising such mixtures. metconazole, myclobutanil, penconazole, propico- 40 [0003] Additionally, the present invention also com- nazole, prothioconazole, mefentrifluconazole, dode- prises a method for protection of plant propagation ma- morph, fenpropimorph, tridemorph; terial (preferably seed) from phytopathogenic fungi or comprising contacting the plant propagation materials C) Lipid and membrane synthesis inhibitors (preferably seeds) with an inventive mixture in fungicid- 45 ally effective amounts. - Phospholipid biosynthesis inhibitors: dimetho- [0004] The term "plant propagation material" is to be morph, mandipropamid, valifenalate, propamo- understood to denote all the generative parts of the plant carb, oxathiapiprolin, 2-{3-[2-(1-{[3,5-bis(dif- such as seeds and vegetative plant material such as cut- luoromethyl-1H-pyrazol-1-yl]acetyl}piperidin-4- tings and tubers (e. g. potatoes), which can be used for yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5- 50 the multiplication of the plant. This includes seeds, roots, yl}phenyl methanesulfonate 2-{3-[2-(1-{[3,5- fruits, tubers, bulbs, rhizomes, shoots, sprouts and other bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}pip- parts of plants, including seedlings and young plants, eridin-4-yl) 1,3-thiazol-4-yl]-4,5-dihydro-1,2-ox- which are to be transplanted after germination or after azol-5-yl}-3-chlorophenyl methanesul-emergence from soil. These young plants may also be fonate,4-[1-[2-[3-(difluoromethyl)-5-methyl- 55 protected before transplantation by a total or partial treat- pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl- ment by immersion or pouring. In a particularly preferred pyridine-2-carboxamide, 4-[1-[2-[3,5-bis(dif- embodiment, the term propagation material denotes luoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N- seeds. 2 3 EP 3 530 118 A1 4 [0005] Additionally, the present invention also com- [0011] Another problem encountered concerns the prises a method for protection of plant propagation ma- need to have available control agents which are effective terial (preferably seed) from phytopathogenic fungi com- against a broad spectrum of harmful fungi. prising contacting the plant propagation materials (pref- [0012] There also exists the need for control agents erably seeds) with the inventive mixture in fungicidally 5 that combine fast action with long lasting action. effective amounts. [0013] Another difficulty in relation to the use of fungi- [0006] Moreover, the invention relates to a method for cides is that the repeated and exclusive application of an controlling phytopathogenic fungi using the inventive individual compound leads in many cases to a rapid se- mixtures and to the use of the compounds present in the lection of harmful fungi, which have developed natural or inventive mixtures for preparing such mixtures, and also 10 adapted resistance against the active compound in ques- to compositions comprising such mixtures. tion. Therefore, there is a need for control agents that [0007] The present invention further relates to plant- help prevent or overcome resistance. protecting active ingredient mixtures having synergisti- [0014] Another problem underlying the present inven- cally enhanced action of improving the health of plants tion is the desire for compositions that improve plants, a and to a method of applying such inventive mixtures to 15 process which is commonly and hereinafter referred to the plants. as "plant health". [0008] Compound I , its preparation as well as its fun- [0015] The term plant health comprises various sorts giicidal is known from WO 2006/087343. Compound II, of improvements of plants that are not connected to the its preparation as well as its fungicidal activity is known control of fungi. For example, advantageous properties from WO 2016/122802. 20 that may be mentioned are improved crop characteristics [0009] Compounds III as well as their fungicidal activity including: emergence, crop yields, protein content, oil and methods for producing them are generally known content, starch content, more developed root system (im- (cf.: http://www.alanwood.net/pesticides/); these sub- proved root growth), improved stress tolerance (e.g. stances are commercially available. The compounds de- against drought, heat, salt, UV, water, cold), reduced eth- scribed by IUPAC nomenclature, their preparation and 25 ylene (reduced production and/or inhibition of reception), their pesticidal activity are also known (cf. Can. J. Plant tillering increase, increase in plant height, bigger leaf Sci. 48(6), 587-94, 1968; EP-A 141 317; EP-A 152 031; blade, less dead basal leaves, stronger tillers, greener EP-A 226 917; EP-A 243 970; EP-A 256 503; EP-A 428 leaf color, pigment content, photosynthetic activity, less 941; EP-A 532 022; EP-A 1 028 125; EP-A 1 035 122; input needed (such as fertilizers or water), less seeds EP-A 1 201 648; EP-A 1 122 244, JP 2002316902; DE 30 needed, more productive tillers, earlier flowering, early 19650197; DE 10021412; DE 102005009458; US grain maturity, less plant verse (lodging), increased shoot 3,296,272; US 3,325,503; WO 98/46608; WO 99/14187; growth, enhanced plant vigor, increased
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