(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 2016/087593 Al 9 June 2016 (09.06.2016) P O P C T (51) International Patent Classification: (74) Agent: SYNGENTA INTERNATIONAL AG; Intellectu C07D 215/46 (2006.01) A01N 43/42 (2006.01) al Property, WRO 1008-Z1-26, Schwarzwaldallee 215, C07D 401/12 (2006.01) A0 43/60 (2006.01) 4058 Basel (CH). C07D 413/12 (2006.01) A0 43/76 (2006.01) (81) Designated States (unless otherwise indicated, for every C07D 405/12 (2006.01) A0 43/84 (2006.01) kind of national protection available): AE, AG, AL, AM, C07D 417/12 (2006.01) AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, (21) International Application Number: BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, PCT/EP20 15/078542 DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KN, KP, KR, (22) International Filing Date: KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, MG, 3 December 2015 (03.12.2015) MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, (25) Filing Language: English PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, (26) Publication Language: English TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (30) Priority Data: (84) Designated States (unless otherwise indicated, for every 14196542.6 5 December 2014 (05. 12.2014) EP kind of regional protection available): ARIPO (BW, GH, (71) Applicant: SYNGENTA PARTICIPATIONS AG GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, [CH/CH]; Schwarzwaldallee 215, 4058 Basel (CH). TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, (72) Inventors: JACOB, Olivier; Syngenta Crop Protection DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, Munchwilen AG, Schaffhauserstrasse, 4332 Stein (FR). LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SULZER-MOSSE, Sarah; Syngenta Crop Protection, SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, Munchwilen AG, Schaffhauserstrasse, 4332 Stein (CH). GW, KM, ML, MR, NE, SN, TD, TG). CEDERBAUM, Fredrik, Emil, Malcolm; Syngenta Crop Protection, Munchwilen AG, Schaffhauserstrasse, 4332 Declarations under Rule 4.17: Stein (CH). HOFFMAN, Thomas James; Syngenta Crop — as to applicant's entitlement to apply for and be granted a Protection, Munchwilen AG, Schaffhauserstrasse, 4332 patent (Rule 4.1 7(H)) Stein (CH). ZAMBACH, Werner; Syngenta Crop Protec — of inventorship (Rule 4.17(iv)) tion, Munchwilen AG, Schaffhauserstrasse, 4332 Stein (CH). WEISS, Matthias; Syngenta Crop Protection, Published: Munchwilen AG, Schaffhauserstrasse, 4332 Stein (CH). — with international search report (Art. 21(3)) (54) Title: NOVEL FUNGICIDAL QUINOLINYL AMIDINE S (I) ©00 (57) Abstract: The invention relates to compounds of formula (I) wherein R 1, R2, R3, R4, R5, R6, R7 and R8 are as defined in the o claims. The invention further provides compositions which comprise these compounds and to their use in agriculture or horticulture for controlling or preventing infestation of plants by phytopathogenic microorganisms, preferably fungi. NOVEL FUNGICIDAL QUINOLINYLAMIDINES The present invention relates to novel microbiocidal, in particular fungicidal, quinolinylamidine compounds. It further relates to compositions which comprise these compounds, and to their use in agriculture or horticulture for controlling or preventing infestation of plants by phytopathogenic microorganisms, preferably fungi. The present invention relates to compounds of formula (I) 2 R and R independently of each other represent hydrogen, Ci-C 4alkyl, Ci-C 4fluoroalkyl or C3- C cycloalkyl; or R and R2 together with the nitrogen atom to which they are attached form a three to six- membered saturated cyclic group which optionally contains either one oxygen atom or one sulphur atom; 3 R represents hydrogen, halogen, cyano, hydroxy, formyl, carboxy, amino, Ci-C 4 alkyl, C2- C5alkenyl, C2-C5alkynl, Ci-C 4haloalkyl, Ci-C alkoxy or C3-C cycloalkyl; 4 R represents hydrogen, halogen, cyano, hydroxy, formyl, carboxy, amino, Ci-C alkyl, C2-C alkenyl, C2-C alkynl, d-C haloalkyl, d-C alkoxy or C3-C cycloalkyl; 5 R represents R -(Z)m- ; R , R ,R8 independently of each other represent hydrogen, halogen, cyano, hydroxy, formyl, carboxy, amino, Ci-C alkyl, C2-C5alkenyl, C2-C5alkynl, Ci-C haloalkyl, Ci-C alkoxy or d - C haloalkoxy; m represents 0 , 1 or 2 ; 10 when m is 0 or 1, Z represents -C(=0)-, -0-, -S-, -S(=0)-, -S(=0) 2- , -N(R )- or d-d alkyl, wherein the alkyl is optionally substituted by one or more groups independently selected from halogen, CN, OH, Ci-C alkylcarbonyl, Ci-C alkoxycarbonyl, Ci-C -haloalkyl, CN, Ci-C -alkoxy and d-C - haloalkoxy; when m is 2 , Z represents Ci-C alkyl, wherein the alkyl is optionally substituted by one or more groups independently selected from halogen, CN, OH, Ci-C alkylcarbonyl, Ci-C alkoxycarbonyl, d - C -haloalkyl, CN, Ci-C -alkoxy and Ci-C -haloalkoxy; 9 R represents hydrogen, d-C 8alkyl, C3-C8alkenyl or C3-C8alkynyl, wherein the alkyl, alkenyl, alkynyl and cycloalkoxyare optionally substituted by one or more groups independently selected from halogen, hydroxyl, cyano, N0 2, OH, SH, d-C alkyl, C2-C alkenyl, C2-C alkynl, d-C haloalkyl, d-C alkoxy, C3-C8 cycloalkyl C3-C8 cycloalkoxy, formyl, C2-C alkylcarbonyl, Ci-C alkylthio, Ci-C alkylsulfinyl and Ci-C alkylsulfonyl; or 9 R represents D-A-Ci-C 6alkyl-, D-A-Ci-C 6alkyl-, D-A-C C alkyl-, D-A-Ci-C 6alkyl-, D-A-d- C alkyl-, D-A-Ci-C6alkyl-, D-A-C2-C alkenyl-, D-A-C2-C alkenyl-, D-A-C2-C alkenyl-, D-A-C2-C alkenyl- , D-A-C2-C alkenyl-, D-A-C2-C alkenyl-, D-A-C2-C alkynyl-, D-A-C2-C alkynyl-, D-A-C2-C alkynyl-, D-A- C2-C alkynyl-, D-A-C2-C alkynyl-, D-A-C2-C alkynyl-, D-A-C3-C cycloalkyl-, D-A-C3-C cycloalkyl-, D-A- C3-C cycloalkyl-, D-A-C3-C cycloalkyl-, D-A-C3-C cycloalkyl- or D-A-C3-C cycloalkyl-; R9 represents an three to eight membered monocyclic system which can be aromatic, partially saturated or fully saturated, which optionally contains one or two hetero atoms selected from the group consisting of N , N(R 1 1 ), O and S, optionally substituted by one or more groups independently selected from the group consisting of hydrogen, halogen, cyano, nitro, mercapto, hydroxy, -CHO, -COOH, - C(=S)NH2, -SF5, d-dalkyl, Ci-C4haloalkyl, C2-C alkenyl, C2-C5haloalkenyl, C2-C5alkynyl, C2- C5haloalkynyl, Ci-C alkoxy, Ci-C haloalkoxy, C3-C cycloalkyl, C3-C halocycloalkyl, C3-C alkenyloxy, C3-C haloalkenyloxy, C3-C5alkynyloxy, C3-C cycloalkyloxy,C2-C alkoxycarbonyl, C2- 2 13 2 13 C4haloalkoxycarbonyl, C2-C5alkylcarbonyl, C2-C5 haloalkylcarbonyl, -N(R )(R ), -C(=0)N(R )(R ), 2 13 C(=S)N(R )(R ), -C4alkylthio, d-dalkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylthio, d - 2 13 dhaloalkylsulfinyl, d-dhaloalkylsulfonyl and -S(=0) 2N(R )(R ); or R9 represents NHR 4 ; A represents -C(=0)-, -C(=S)-, -C(=NOR15 )-, -C(R )=NO-, -ON=C(R15 )-, -S(=0)(=NR 15 )-, - 15 10 15 S(=0)(R )=N-, -0-C(=0)-, -C(=0)-0-, -0-, -S-, -S(=0)-, -S(=0) 2- , -S(=0)(=NR )-, -N(R )-, -N(R )- 15 15 (C=0)-, -(C=0)-N(R )-, -N(R )-S0 2- or -S0 2-N(R )-; D represents d-dalkyl, d-dalkenyl, d-dalkynyl, d-dcycloalkyl, benzyl, phenyl each of which are optionally substituted by one or more groups independently selected from halogen, cyano, hydroxy, mercapto, d-dhaloalkyl, d-dalkoxy, formyl, C2-C5alkylcarbonyl, d-dalkoxycarbonyl, d - dalkylthio, d-dhaloalkylthio, d-dalkylsulfinyl and d-dalkylsulfonyl; 0 R represents hydrogen, formyl, d-dalkyl, d-dhaloalkyl, C3-C5alkenyl or d-dalkylcarbonyl; each R independently represents hydrogen, formyl, d-dalkyl, d-dhaloalkyl, d-dalkoxy, d-dhaloalkoxy, d-dalkenyl, C3-C5haloalkenyl, d-dalkylcarbonyl, d-dalkoxycarbonyl, d-d haloalkylcarbonyl, benzyl, phenyl, d-dalkylsulfinyl, d-dalkylsulfonyl, d-dhaloalkylsulfinyl, d - 2 13 2 13 2 13 dhaloalkylsulfonyl -C(=0)N(R )(R ), -C(=S)N(R )(R ) or -S(=0) 2N(R )(R ), wherein the alkyl, haloalkyl, alkoxy, haloalkoxy, benzyl and phenyl are optionally substituted by one or more groups independently selected from halogen, cyano, hydroxy, d-dalkyl, d-dhaloalkyl, d-dalkoxy and d - dhaloalkoxy; each R 2 and R 3 independently of each other represents hydrogen, formyl, d-dalkyl, d - dhaloalkyl, d-dalkylcarbonyl, d-dalkoxycarbonyl, benzyl or phenyl; or R 2 and R 3 together with the nitrogen atom to which they are attached form a three to six- membered saturated cyclic group which optionally contains either one oxygen atom or one sulphur atom; R 4 represents phenyl optionally substituted by fluoro, CN, OH, methyl, ethyl, n-propyl, iso- propyl, n-butyl, iso-butyl, sec-butyl, tert-butyl, CH2F, CHF2, CF3, CHF-CH3, CF2-CH3, CF2-CH3, CF2- CF3, OMe, OEt, OiPr, OPr, OCHF2 and OCF3; 5 each R independently represents hydrogen, C -C4alkyl, C -C4haloalkyl, C3-C5alkenyl, C3- C5haloalkenyl, C3-C5alkynyl, C3-C cycloalkyl, benzyl or phenyl wherein the alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, cycloalkyl, benzyl and phenyl are optionally substituted by one or more groups independently selected from halogen, cyano, hydroxy, C -C4alkyl, C -C4haloalkyl, C -C alkoxy and - C haloalkoxy; and tautomers/isomers/enantiomers/salts and N-oxides of these compounds.