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WO 2015/014733 Al 5 February 2015 (05.02.2015) P O P C T

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WO 2015/014733 Al 5 February 2015 (05.02.2015) P O P C T (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization I International Bureau (10) International Publication Number (43) International Publication Date WO 2015/014733 Al 5 February 2015 (05.02.2015) P O P C T (51) International Patent Classification: (81) Designated States (unless otherwise indicated, for every C07D 233/64 (2006.01) C07D 403/06 (2006.01) kind of national protection available): AE, AG, AL, AM, A 43/40 (2006.01) C07D 239/26 (2006.01) AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, A 43/50 (2006.01) C07D 417/06 (2006.01) BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, A0 43/54 (2006.01) C07D 249/08' (2006.01) DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, A0 43/653 (2006.01) C07D 213/57 (2006.01) HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KN, KP, KR, C07D 401/06 (2006.01) KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, (21) International Application Number: OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, PCT/EP2014/065994 SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, (22) International Filing Date: TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, 25 July 2014 (25.07.2014) ZW. (25) Filing Language: English (84) Designated States (unless otherwise indicated, for every kind of regional protection available): ARIPO (BW, GH, (26) Publication Language: English GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, SZ, TZ, (30) Priority Data: UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, 2256/DEL/2013 29 July 2013 (29.07.2013) IN TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, (71) Applicant: SYNGENTA PARTICIPATIONS AG MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, [CH/CH]; Schwarzwaldallee 215, CH-4058 Basel (CH). TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, KM, ML, MR, NE, SN, TD, TG). (72) Inventors: JEANMART, Stephane Andre Marie; Syn- genta Crop Protection Munchwilen AG, Schaffhauser- Declarations under Rule 4.17 : strasse, CH-4332 Stein (CH). RAJAN, Ramya; Santa — as to applicant's entitlement to apply for and be granted a Monica Works, Corlim Ilhas, Goa 403 110 (IN). BON- patent (Rule 4.1 7(H)) VALOT, Damien; Syngenta Crop Protection Munchwilen AG, Schaffhauserstrasse, CH-4332 Stein (CH). PERRUC- — of inventorship (Rule 4.17(iv)) CIO, Francesca; Syngenta Crop Protection Munchwilen Published: AG, Schaffhauserstrasse, CH-4332 Stein (CH). — with international search report (Art. 21(3)) (74) Agent: SYNGENTA INTERNATIONAL AG; Intellectu al Property, WRO 1008-Z1 -26, Schwarzwaldallee 215, CH-4058 Basel (CH). (54) Title: NOVEL MICROBIOCIDES (I) (57) Abstract: Compounds of formula (I) wherein the other substituents HetAr, R 1, R2, R3, R4, R5, R6, R7 and R8 are as defined in claim 1, and their use in compositions and methods for the control and/or prevention of microbial infection, particularly fungal in fection, in plants and to processes for the preparation of these compounds. Novel Microbiocides The present invention relates to novel microbiocidally active, in particular fungicidally active, alkyl-alkyne or cycloalkyl-alkyne containing compounds their use in compositions and methods for the control and/or prevention of microbial infection, particularly fungal infection, in plants and to processes for the preparation of these compounds. The incidence of serious microbial infections, particularly fungal infections, either systemic or topical, continues to increase for plants. Fungicides are compounds, of natural or synthetic origin, which act to protect plants against damage caused by fungi. Current methods of agriculture rely heavily on the use of fungicides. In fact, some crops cannot be grown usefully without the use of fungicides. Using fungicides allows a grower to increase the yield of the crop and consequently, increase the value of the crop. Numerous fungicidal agents have been developed. However, the treatment of fungal infestations continues to be a major problem. Furthermore, fungicide resistance has become a serious problem, rendering these agents ineffective for some agricultural uses. As such, a need exists for the development of new fungicidal compounds. The present invention accordingly relates to compounds of formula (I) wherein HetAr is an optionally substituted 5 to 10 membered heteroaromatic ring system which may be monycyclic or bicyclic n is an integer with a value of 0,1 ,2 or 3 R and R2 are independently halogen or R and R2 together with the carbon atom to which they are attached form an optionally substituted 3- to 8-membered ring, optionally containing an oxygen, sulphur or nitrogen atom 3 CrC CrC (Ci-C R is hydroxy, 6alkoxy, 6haloalkoxy, cyano, halo, or -OSi 6alkyl)3 4 CrC CrC CrC R is 6alkyl, 6haloalkly, optionally substituted 8cycloalkyl or an optionally CrC substituted 8halocycloalkyl 5 Ci-C CrC R is independently alkyl, cyano, 6haloalkyl, hydroxy, 6alkoxy, halogen, or d - C6haloalkoxy; m is an integer with a value of 0, 1, 2 or 3 6 CrC CrC CrC R is hydrogen, 6alkyl, 6haloalkyl, optionally substituted 8cycloalkyl, optionally substituted 4 to 11 membered heterocyclyl, optionally substituted 6 to 10 membered aryl which may be monycyclic or bicyclic or an optionally substituted 5 to 10 membered heteroaromatic which may be monycyclic or bicyclic or R , R2 and R6 together can form a triple bond to form an optionally substituted d - C7alkynyl 7 8 CrC CrC R and R are independently hydrogen, 6alkyl or 6haloalkyl or R7 and R8 together with the carbon atoms to which they are attached form an optionally substituted 3- to 8-membered ring, optionally containing an oxygen, sulphur or nitrogen atom or a agronomically acceptable salt or a N-oxide thereof, with the proviso that if n is an integer with a value of 1,2 or 3, then R6 cannot be hydrogen, C C6alkyl or C C6haloalkyl. When present, the optional substituents on aryl and on heteroaryl include one or more of CrC CrC CrC halogen, nitro, cyano, hydroxyl, amino, 6alkyl, 6haloalkyl, 6alkoxy, d - CrC C6haloalkoxy, C3-C6cycloalkyl (itself optionally substituted with 6alkyl, halogen or d - CrC C6haloalkyl), C3-C6halocycloalkyl (itself optionally substituted with 6alkyl, halogen or d - CrC C6haloalkyl), C3-C6cycloalkyloxy (itself optionally substituted with 6alkyl, halogen or d - C6haloalkyl), optionally substituted aryl, optionally substituted heterocyclyl, optionally substituted heteroaryl. Preferred optional substituents are on aryl and on heteroaryl halogen, cyano, d-C 6alkyl, d - C6haloalkyl, d-C 6alkoxy, d-C 6haloalkoxy, C3-C6cycloalkyl, C3-C6halocycloalkyl, C3- C6cycloalkyloxy, optionally substituted aryl, optionally substituted aryl heterocyclyl, optionally substituted heteroaryl. More preferred optional substituents on aryl and on heteroaryl are halogen, cyano, d - C6alkyl, d-C 6haloalkyl, d-C 6alkoxy, d-C 6haloalkoxy, C3-C6cycloalkyl, d-C 6halocycloalkyl. When present, the optional substituents on cycloalkyi, on heterocyclyl include one or more of halogen, nitro, cyano, hydroxyl, amino, d-C 6alkyl, d-C 6haloalkyl, d-C 6alkoxy, d - C6haloalkoxy, C3-C6cycloalkyl (itself optionally substituted with d-C 6alkyl, halogen or d - C6haloalkyl), C3-C6halocycloalkyl (itself optionally substituted with d-C 6alkyl, halogen or d - C6haloalkyl), C3-C6cycloalkyloxy (itself optionally substituted with CrC 6alkyl, halogen or - C6haloalkyl), optionally substituted aryl, optionally substituted heterocyclyl, optionally X x X X x substituted heteroaryl, =0, =NR , =NOR , =NNH(R ), =NN(R )2 wherein R is an C C6alkyl. Preferred optional substituents on cycloalkyl and on heterocyclyl are halogen, cyano, C C6alkyl, CrC 6haloalkyl, CrC 6alkoxy, CrC 6haloalkoxy, C3-C6cycloalkyl, C3-C6halocycloalkyl, C3-C6cycloalkyloxy, optionally substituted aryl, optionally substituted aryl heterocyclyl, optionally substituted heteroaryl. More preferred optional substituents on cycloalkyl and on heterocyclyl are halogen, cyano, CrC 6alkyl, CrC 6haloalkyl, CrC 6alkoxy, CrC 6haloalkoxy, C3-C6cycloalkyl, C3- C6halocycloalkyl. Where substituents are indicated as being optionally substituted, this means that they may or may not carry one or more identical or different substituents, e.g. one to three substituents. Normally not more than three such optional substituents are present at the same time. Where a group is indicated as being substituted, e.g. alkyl, this includes those groups that are part of other groups, e.g. the alkyl in -C(=0)(alkyl). The term "halogen" refers to fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine and most preferably fluorine and chlorine. Alkyl substituents may be straight-chained or branched. Alkyl on its own or as part of another substituent is, depending upon the number of carbon atoms mentioned, for example, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl and the isomers thereof, for example, iso-propyl, iso-butyl, sec-butyl, tert-butyl or iso-amyl. Preferred alkyl groups are methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, iso-propyl, iso-butyl, sec-butyl, tert-butyl or iso-amyl. Haloalkyl groups may contain one or more identical or different halogen atoms and, for example, may stand for CH2CI, CHCI2, CCI3, CH2F, CHF2, CF3, CF3CH2, CH3CF2, CF3CF2 or CCI3CCI2. The preferred haloalkyl groups are CH2CI, CHCI2, CCI3, CH2F, CHF2, CF3, CF3CH2, CH3CF2, CF3CF2 or CCI3CCI2. Alkoxy means a radical -OR, where R is alkyl, e.g. as defined above. Alkoxy groups include, but are not limited to, methoxy, ethoxy, 1-methylethoxy, propoxy, butoxy, 1-methylpropoxy and 2-methylpropoxy. The preferred alkyl groups are methoxy, ethoxy, 1-methylethoxy, propoxy, butoxy, 1-methylpropoxy and 2-methylpropoxy. Haloalkoxy means a radical -OR, where R is haloalkyl, e.g. as defined above. Haloalkoxy groups include, but are not limited to, CH2CIO-, CHCI2 0-, CCI3 0-, CH2F 0-, CHF2 0-, CF3 Ο Ο Ο -, CF3CH2 -, CH3CF2 -, CF3CF2 O- or CCI3CCI2 0-.
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