US 12,012,399 B2
Microbiocidal quinoline dihydro-(thiazine)oxazine derivatives
Farhan Bou Hamdan, Stein (CH); Matthias Weiss, Stein (CH); and Laura Quaranta, Basel (CH)
Assigned to SYNGENTA PARTICIPATIONS AG, Basel (CH)
Appl. No. 17/282,109
Filed by SYNGENTA PARTICIPATIONS AG, Basel (CH)
PCT Filed Oct. 1, 2019, PCT No. PCT/EP2019/076600
§ 371(c)(1), (2) Date Apr. 1, 2021,
PCT Pub. No. WO2020/070131, PCT Pub. Date Apr. 9, 2020.
Claims priority of application No. 18199016 (EP), filed on Oct. 6, 2018.
Prior Publication US 2021/0371408 A1, Dec. 2, 2021
Int. Cl. C07D 413/04 (2006.01); A01N 43/86 (2006.01); C07D 417/04 (2006.01)
CPC C07D 413/04 (2013.01) [A01N 43/86 (2013.01); C07D 417/04 (2013.01)] 15 Claims
 
1. A compound of formula (I)

OG Complex Work Unit Chemistry
wherein
X is O or S;
R1 is hydrogen, halogen, methyl or cyano;
R2 is hydrogen, halogen, methyl or cyano;
R3 and R4 are each independently hydrogen, halogen or methyl;
R5 and R6 are each independently selected from hydrogen, halogen, C1-C5 alkoxy, C1-C5 alkyl, C3-C5 cycloalkyl, C2-C5 alkenyl or C2-C5 alkynyl, wherein the alkyl, cycloalkyl, alkenyl and alkynyl groups may be optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3 alkoxy and C1-C3 alkylthio; or
R5 and R6 together with the carbon atom to which they are attached represent C3-C6 cycloalkyl or C4-C6 cycloalkenyl, wherein the cycloalkyl and cycloalkenyl groups may be optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3 alkoxy and C1-C3 alkylthio;
R7 is hydrogen, C1-C4 alkyl, C1-C4 haloalkyl or C3-C4 cycloalkyl, wherein the alkyl and cycloalkyl, may be optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3 alkoxy and C1-C3 alkylthio;
R8 and R9 are each independently selected from hydrogen, halogen, C1-C4 alkyl and C1-C4 alkoxy; or
R8 and R9 together with the carbon atom to which they are attached represent ═O, ═NORa, C3-C5 cycloalkyl, wherein the cycloalkyl may be optionally substituted with 1 to 3 substituents independently selected from halogen, cyano, C1-C3 alkyl, C1-C3 alkoxy and C1-C3 alkylthio;
each R10 independently represents halogen, nitro, cyano, formyl, C1-C5 alkyl, C2-C5 alkenyl, C2-C5 alkynyl, C3-C6 cycloalkyl, C1-C5 alkoxy, C3-C5 alkenyloxy, C3-C5 alkynyloxy, C1-C5 alkylthio, —C(═NORb)C1-C5 alkyl, or C1-C5 alkylcarbonyl, wherein the alkyl, cycloalkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy and alkylthio may be optionally substituted with 1 to 5 substituents independently selected from halogen, C1-C3 alkyl, C1-C3 alkoxy, cyano and C1-C3 alkylthio; n is 0, 1, 2 or 3;
Ra is independently selected from hydrogen, C1-C4 alkyl, C2-C4 alkenyl, C3-C4 alkynyl, C3-C4 cycloalkyl(C1-C2)alkyl and C3-C4 cycloalkyl, wherein the alkyl, cycloalkyl, alkenyl and alkynyl groups may be optionally substituted with 1 to 3 substituents independently selected from halogen and cyano; and
Rb is independently selected from hydrogen, C1-C4 alkyl, C2-C4 alkenyl, C3-C4 alkynyl, C3-C4 cycloalkyl(C1-C2)alkyl and C3-C4 cycloalkyl, wherein the alkyl, cycloalkyl, alkenyl and alkynyl groups may be optionally substituted with 1 to 3 substituents independently selected from halogen and cyano;
or a salt, enantiomer or N-oxide thereof.