(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 2017/067839 Al 27 April 2017 (27.04.2017) P O P C T (51) International Patent Classification: (81) Designated States (unless otherwise indicated, for every C07D 311/76 (2006.01) C07C 257/12 (2006.01) kind of national protection available): AE, AG, AL, AM, A 37/52 (2006.01) C07D 405/04 (2006.01) AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, A 43/16 (2006.01) C07D 409/04 (2006.01) BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DJ, DK, DM, A 43/56 (2006.01) C07D 491/20 (2006.01) DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, A01N 43/90 (2006.01) HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KN, KP, KR, KW, KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, (21) International Application Number: MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, PCT/EP20 16/074545 OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, (22) International Filing Date: SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, 13 October 2016 (13.10.201 6) TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (25) Filing Language: English (84) Designated States (unless otherwise indicated, for every (26) Publication Language: English kind of regional protection available): ARIPO (BW, GH, (30) Priority Data: GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, 15 19 1178. 1 23 October 2015 (23. 10.2015) EP TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, (71) Applicant: SYNGENTA PARTICIPATIONS AG DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, [CH/CH]; Schwarzwaldallee 215, 4058 Basel (CH). LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, (72) Inventors: WEISS, Matthias; Syngenta Crop Protection GW, KM, ML, MR, NE, SN, TD, TG). AG, Schaffhauserstrasse, 4332 Stein (CH). SULZER- MOSSE, Sarah; Syngenta Crop Protection AG, Schaff Declarations under Rule 4.17 : hauserstrasse, 4332 Stein (CH). GAGNEPAIN, Julien, — as to applicant's entitlement to apply for and be granted a Daniel, Henri; Syngenta Crop Protection AG, Schaffhaus patent (Rule 4.1 7(H)) erstrasse, 4332 Stein (CH). HOFFMAN, Thomas, James; Syngenta Crop Protection AG, Schaffhauserstrasse, 4332 — of inventorship (Rule 4.17(iv)) Stein (CH). ZAMBACH, Werner; Syngenta Crop Protec Published: tion AG, Schaffhauserstrasse, 4332 Stein (CH). — with international search report (Art. 21(3)) (74) Agent: SYNGENTA INTERNATIONAL AG; Schwar zwaldallee 215 (WRO B8-Z1-30), 4058 Basel (CH). (54) Title: MICROBICIDAL PHENYL AMIDINE DERIVATIVES o (57) Abstract: Compounds of the formula (I), wherein R 1, R2, R3, Q1, Q2, Q3, R4, R5, R6, R7, R8 and R9 are as defined in claim 1. Fur o thermore, the present invention relates to agrochemical compositions which comprise compounds of formula (I), to preparation of these compositions, and to the use of the compounds or compositions in agriculture or horticulture for combating, preventing or con trolling infestation of plants, harvested food crops, seeds or non-living materials by phytopathogenic microorganisms, in particular fungi. Microbiocidal Phenylamidine Derivatives The present invention relates to novel phenylamidine derivatives, which have microbiocidal activity, e.g. as active ingredients, in particular fungicidal activity. The invention also relates to preparation of these phenylamidine derivatives, to intermediates useful in the preparation of these phenylamidine derivatives, to the preparation of these intermediates, to agrochemical compositions which comprise at least one of the phenylamidine derivatives, to preparation of these compositions and to the use of the phenylamidine derivatives or compositions in agriculture or horticulture for controlling or preventing infestation of plants, harvested food crops, seeds or non-living materials by phytopathogenic microorganisms, in particular fungi. Certain fungicidal phenylamidine compounds are described in WO 00/46184. It has now surprisingly been found that certain novel bicyclic phenylamidine derivatives have favourable fungicidal properties. The present invention therefore provides compounds of formula (I) R and R2 each independently represent hydrogen, C i-C4 alkyl, C i-C4fluoroalkyl, C2- C 2 C4 alkenyl, -C4 alkynyl or C3-C6cycloalkyl; or R and R2 together with the nitrogen atom to which they are attached form a three to six- membered saturated cyclic group which may optionally contain one oxygen or one sulphur atom; R3 represents fluoro, chloro, bromo, cyano, C 1- C 4 alkyl, C 2- C 4 alkenyl, C 1- C 4 haloalkyl, C 1- C 4 alkoxy, C 1-C 3 fluoroalkoxy or C3-C6 cycloalkyl; Q 1, Q2 and Q3 each independently represent -C(R6)(R7)- or -0-, wherein the -Q1- Q2-Q3- linkage does not contain contiguous oxygen atoms; R4 and R5 each independently represents hydrogen, cyano, aryl (which may be substituted with one to three R8 groups), heteroaryl (which may be substituted with one or two R8 groups), heterocyclyl (which may be substituted with one or two R8 groups), hydroxy, Ci-Cs alkyl, C 2-C 8 alkenyl, C 2-C s alkynyl, Ci-Cs haloalkyl, Ci-Cs alkoxy, C3-C8 cycloalkyl (which may be substituted with one to three R8 groups); or R4 and R5 together with the carbon atom to which they are attached form a three to eight- membered saturated or partially-unsaturated carbocyclic group (which may be substituted with one to three R8 groups, and which may contain one or two oxygen atoms, one or two sulphur atoms or NR9, wherein R9 is hydrogen, C1-C4 alkoxy, C2-C4 alkynyl or Ci- C4 alkyl); R6 and R7 each independently represent hydrogen, fluoro, C1-C3 alkyl, Ci-Csfluoroalkyl 6 7 or C 3-C5 cycloalkyl ; or R and R together with carbon atom to which they are attached to form a three to six membered saturated cyclic group which may optionally contain an oxygen or sulfur atom; and Each R8 independently represents fluoro, chloro, bromo, cyano, C1-C4 alkyl, C2-C4 alkenyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C3 fluoroalkoxy, C2-C4 alkynyl or C3-C6 cycloalkyl; or two R8 groups on the same carbon atom are taken together with the carbon atom to form the radical C=X, wherein X represents CH2, CF2, O or N-0-Ci-C4alkyl; or a salt or N-oxide thereof. In a second aspect the present invention provides an agrochemical composition comprising a compound of formula (I). Compounds of formula (I) may be used to control phytopathogenic microorganisms. Thus, in order to control a phytopathogen a compound of formula (I), or a composition comprising a compound of formula (I), according to the invention may be applied directly to the phytopathogen, or to the locus of a phytopathogen, in particular to a plant susceptible to attack by phytopathogens. Thus, in a third aspect the present invention provides the use of a compound of formula (I), or a composition comprising a compound of formula (I), as described herein to control a phytopathogen. In a further aspect the present invention provides a method of controlling phytopathogens, comprising applying a compound of formula (I), or a composition comprising a compound of formula (I), as described herein to said phytopathogen, or to the locus of said phytopathogen, in particular to a plant susceptible to attack by a phytopathogen. Compounds of formula (I) are particularly effective in the control of phytopathogenic fungi. Thus, in a yet further aspect the present invention provides the use of a compound of formula (I), or a composition comprising a compound of formula (I), as described herein to control phytopathogenic fungi. In a further aspect the present invention provides a method of controlling phytopathogenic fungi, comprising applying a compound of formula (I), or a composition comprising a compound of formula (I), as described herein to said phytopathogenic fungi, or to the locus of said phytopathogenic fungi, in particular to a plant susceptible to attack by phytopathogenic fungi. 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 alkylthio. The term "halogen" refers to fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine. 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, ie -butyl or iso-amyl. Alkenyl substituents (either alone or as part of a larger group, eg. alkenyloxy) can be in the form of straight or branched chains, and the alkenyl moieties, where appropriate, can be of either the (E)- or (Z)-configuration. Examples are vinyl and allyl. The alkenyl groups are preferably C2-C6, more preferably C2-C4 and most preferably C2-C3 alkenyl groups. Alkynyl substituents (either alone or as part of a larger group, eg. alkynyloxy) can be in the form of straight or branched chains. Examples are ethynyl and propargyl. The alkynyl groups are preferably C2-C6, more preferably C2-C4 and most preferably C2-C3 alkynyl groups.