(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 2014/082880 Al 5 June 2014 (05.06.2014) P O P C T (51) International Patent Classification: HADEN, Egon; Maulbronner Hof 24, 67346 Speyer (DE). C07D 249/10 (2006.01) A01N 43/653 (2006.01) ESCRIBANO CUESTA, Ana; SpelzenstraBe 16, 68167 C07D 303/22 (2006.01) C07C 217/34 (2006.01) Mannheim (DE). (21) International Application Number: (81) Designated States (unless otherwise indicated, for every PCT/EP20 13/074009 kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, (22) International Filing Date: BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, 18 November 2013 (18.1 1.2013) DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, (25) Filing Language: English HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, (26) Publication Language: English MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, (30) Priority Data: OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, 61/730,091 27 November 2012 (27. 11.2012) US SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, 12194433.4 27 November 2012 (27. 11.2012) EP TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, 13 150668.5 9 January 2013 (09.01 .2013) EP ZW. (71) Applicant: BASF SE [DE/DE]; 67056 Ludwigshafen 4 Designated States (unless otherwise indicated, for every (DE). kind of regional protection available): ARIPO (BW, GH, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, SZ, TZ, (72) Inventors: GRAMMENOS, Wassilios; Alexander-Flem- UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, ing-Str. 13, 67071 Ludwigshafen (DE). CRAIG, Ian TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, Robert; Carl-Bosch-StraBe 70, 67063 Ludwigshafen (DE). EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, BOUDET, Nadege; Auf der Au 12, 69502 Hemsbach MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, (DE). MULLER, Bernd; Stockingerstr. 7, 67227 TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, Frankenthal (DE). DIETZ, Jochen; Kaethe-Koll- KM, ML, MR, NE, SN, TD, TG). witz-Strasse 26a, 76227 Karlsruhe (DE). LAUTER- Published: WASSER, Erica May Wilson; Burklin-Wolf-Strasse 39, 67157 Wachenheim (DE). LOHMANN, Jan Klaas; — with international search report (Art. 21(3)) Muhltorstr 2a, 67245 Lambsheim (DE). GROTE, Thomas; Im Hohnhausen 18, 67157 Wachenheim (DE). (54) Title: SUBSTITUTED [1,2,4] TRIAZOLE COMPOUNDS o 00 00 o00 (57) Abstract: The present invention relates to substituted [1,2,4] triazol compounds of the formula I wherein the substituents are o defined in the claims and the description, and the N-oxides and the salts thereof for combating phytopathogenic fungi, and to the use and methods for combating phytopathogenic fungi and to seeds coated with at least one such compound. The invention also relates o to processes for preparing these compounds, intermediates, processes for preparing such intermediates, and to compositions com prising at least one compound I. Substituted [ 1 ,2,4]triazole compounds Description The present invention relates to substituted [ 1 ,2,4]triazol compounds and the N-oxides and the salts thereof for combating phytopathogenic fungi, and to the use and methods for combating phytopathogenic fungi and to seeds coated with at least one such compound. The invention also relates to processes for preparing these compounds, intermediates, processes for prepar ing such intermediates, and to compositions comprising at least one compound I. EP 0 126 430 A2 relates to a process for the preparation of 1-triazolylethylether derivatives. EP 0 113 640 A2 relates to 1-azolyl-2-aryl-3-fluoroalkan-2-ols as microbiocides. DE 3801233 re- lates to 1-phenoxyphenyl-2-triazolyl-ethanolethers as microbiocides. EP 0 275 955 A 1 relates to 1-phenoxyphenyl-1-triazolylmethyl-carbinols as microbiocides. GB 2 130 584 A is directed to microbiocidal 1-carbonyl-1-phenoxyphenyl-2-azolylethanol-derivatives. WO 2013/010862 (PCT/EP2012/063526), WO 2013/010894 (PCT/EP20 12/063635), WO 2013/010885 (PCT/EP2012/063620), WO 2013/024076 (PCT/EP20 12/065835), WO 2013/024075 (PCT/EP2012/065834), WO 2013/024082 (PCT/EP20 12/065850), WO 2013/024077 (PCT/EP2012/065836), WO 2013/024081 (PCT/EP20 12/065848), WO 2013/024080 (PCT/EP2012/065847), PCT/EP20 12/065852 (PCT/EP20 12/065852) and EP 2559688 (EP 11177556.5) are directed to specific fungicidal substituted 2-[2-halogen-4-phenoxy-phenyl]-1- [ 1 ,2,4]triazol-1-yl-ethanol compounds. EP 0 077 479 A2 relates to phenoxyphenyl-azolylmethyl- ketons and -carbinols, processes for their preparation and their use as intermediates and as fungicides. EP 0 077 479 A2 does not contain any compound, wherein at the "inner phenyl" a substituent corresponding to the inventive R3 is present. EP 0 117 378 A 1 is directed to1- carbonyl-1-phenoxyphenyl-2-azolyl-ethynol derivatives and their use as microbiocides. WO 2010/1461 14 A 1 relates to triazole compounds carrying a sulfur substituent and to precursors thereof. J. Agric. Food. Chem. 2009, 57, 4854-4860 relates to the synthesis and fungicidal eval uation of certain 2-arylphenyl ether-3-(1 H-1 ,2,4-triazol-1-yl)propan-2-ol derivatives. EP 0 440 950 A2 is directed to halgenallyl-azolyl-derivatives of the formula , wherein 1 and X2 are halogen and X3 is hydrogen or halogen. CN 101225074 A relates to compounds , i.e. to phenoxy- phenyl substituted triazole compounds, wherein the substituent corresponding to „R " of the present invention is phenylalkenyl. In many cases, in particular at low application rates, the fungicidal activity of the known fungi cidal compounds is unsatisfactory. Based on this, it was an object of the present invention to provide compounds having improved activity and/or a broader activity spectrum against phyto- pathogenic harmful fungi. Surprisingly, this object is achieved by the use of the inventive substituted [ 1 ,2,4]triazol com pounds of formula I having favorable fungicidal activity against phytopathogenic fungi. Accordingly, the present invention relates to the com ounds of formula I: wherein R is Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, C3-C8 -cycloalkyl-Ci-C6-alkyl, phenyl or phenyl-Ci-C4-alkyl; R2 is hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, Cs-Cs-cycloalkyl- Ci-C6-alkyl, phenyl, phenyl-Ci-C4-alkyl, phenyl-C2-C4-alkenyl or phenyl-C2-C4-alkynyl wherein the aliphatic moieties of R and/or R2 may carry one, two, three or up to the maximum possible number of identical or different groups R 2a which independently of one another are selected from: R 2a halogen, O H, C N, nitro, Ci-C4-alkoxy, Cs-Cs-cycloalkyl, Cs-Cs-halocycloalkyl and C1-C4- halogenalkoxy; wherein the cycloalkyl and/or phenyl moieties of R and/or R2 may carry one, two, three, four, five or up to the maximum number of identical or different groups R 2 which independently of one another are selected from: 2b R halogen, O H, C N, nitro, Ci-C 4-alkyl, Ci-C 4-alkoxy, Ci-C 4-halogenalkyl, Cs-Cs-cycloalkyl, C 3-Cs-halocycloalkyl and Ci-C4-halogenalkoxy R3 is halogen; R4 is independently selected from halogen, C N, NO2, O H, S H, Ci-C6-alkyl, Ci-C6-alkoxy, C2-C6-alkenyl, C2-C6-alkynyl, Cs-Cs-cycloalkyl, Cs-Cs-cycloalkyloxy, NH2, NH(Ci-C 4-alkyl), N(Ci-C 4-alkyl) 2, N H(C 3-C6-cycloalkyl), N(C 3-C6-cycloalkyl)2, S(0) P(Ci-C 4-alkyl), alkyl), C(=0)(OH), C(=0)(0-Ci-C 4-alkyl), C(=0)(N H(Ci-C 4-alkyl)), C(=0)(N(Ci-C 4-alkyl) 2), C(=0)(N H(C -C C(=0)-(N(C 4 is 3 6-cycloalkyl)) and 3 -C6 -cycloalkyl) 2; wherein each of R unsubsti- tuted or further substituted by one, two, three or four R4a; wherein 4a R is independently selected from halogen, C N, NO2, O H, Ci-C4-alkyl, Ci-C4-haloalkyl, C3-C8- cycloalkyl, Cs-Cs-halocycloalkyl, Ci-C4-alkoxy and Ci-C4-haloalkoxy; p is 0, 1 or 2 ; m is 0 , 1, 2 , 3 , 4 or 5 ; with the proviso that if m=1 , R4 is not para-halogen; 3 4 with the proviso that if R is C I and m=2, (R )m is not 2,4-di-halogen, wherein each halogen is selected from C I and F; and 3 4 with the proviso that if R is C I and m=3, (R )m is not 2,4,6-tri-halogen, wherein each halogen is selected from C I and F; and the N-oxides and the agriculturally acceptable salts thereof. In a particular embodiment, the provisos are as follows: with the proviso that if m=1 , R4 is not para-halogen; 3 4 with the proviso that if R is C I and m=2, (R )m is not 2,4-di-halogen; and 3 4 with the proviso that if R is C I and m=3, (R )m is not 2,4,6-tri-halogen; According to a more particular embodiment, the provisos are as follows: with the proviso that if m=1 , R4 is not para-halogen; 4 with the proviso that if m=2, (R )m is not 2,4-di-halogen; and 4 with the proviso that if m=3, (R )m is not 2,4,6-tri-halogen.