US 12,281,081 B2
Herbicidal compounds
Alan Joseph Hennessy, Bracknell (GB); Elizabeth Pearl Jones, Bracknell (GB); Suzanna Jane Dale, Bracknell (GB); Alexander William Gregory, Bracknell (GB); Ian Thomas Tinmouth Houlsby, Bracknell (GB); Yunas Bhonoah, Bracknell (GB); and Julia Comas-Barcelo, Bracknell (GB)
Assigned to SYNGENTA CROP PROTECTION AG, Basel (CH)
Appl. No. 17/429,516
Filed by SYNGENTA CROP PROTECTION AG, Basel (CH)
PCT Filed Feb. 10, 2020, PCT No. PCT/EP2020/053349
§ 371(c)(1), (2) Date Aug. 9, 2021,
PCT Pub. No. WO2020/165102, PCT Pub. Date Aug. 20, 2020.
Claims priority of application No. 1901878 (GB), filed on Feb. 11, 2019.
Prior Publication US 2022/0089543 A1, Mar. 24, 2022
Int. Cl. C07D 221/20 (2006.01); A01N 25/32 (2006.01); A01N 43/32 (2006.01); A01N 43/42 (2006.01); A01N 43/84 (2006.01); A01P 13/00 (2006.01)
CPC C07D 221/20 (2013.01) [A01N 25/32 (2013.01); A01N 43/42 (2013.01); A01N 43/84 (2013.01); A01P 13/00 (2021.08)] 16 Claims
 
1. A compound of Formula (I)

OG Complex Work Unit Chemistry
wherein
R1 is selected from the group consisting of methyl, ethynyl, 1-propynyl, phenyl and a 5 or 6 membered heteroaryl which comprises one or two nitrogen heteroatoms, said phenyl and heteroaryl optionally substituted by one or two R9 substituents;
R2 is selected from the group consisting of methyl, ethyl, methoxy and chloro;
R3 is selected from the group consisting of methyl, ethyl, methoxy and chloro;
R4 is —S(O)2NR5R6 or —S(O)(═NR7)R8;
R5 is hydrogen or C1-C6alkyl; and
R6 is selected from the group consisting of hydrogen, C1-C6alkyl, C3-C6cycloalkyl, C1-C6 alkoxy-C1-C3alkyl-, —C(O)C1-C6alkyl, —C(O)OC1-C6alkyl and CH2CN; or
R5 and R6 together form —CH2CH2OCH2CH2—, —CH2CH2S(O)2CH2CH2—; and
R7 is hydrogen or C1-C6alkyl;
R8 is selected from the group consisting of hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C3-C6cycloalkyl, phenyl,-pyridyl, wherein the phenyl and pyridyl are optionally substituted by one, two or three substituents independently selected from the group consisting of C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C2-C3alkenyl, C2-C3alkynyl, halogen, cyano and nitro;
R9 is independently selected from the group consisting of C1-C4 alkyl, C1-C4 haloalkyl, cyano and halogen;
G is selected from the group consisting of hydrogen, —(CH2)n—Ra, —C(O)—Ra, —C(O)—(CRcRd)n—O—Rb, —C(O)—(CRcRd)n—S—Rb, —C(O)NRaRa, —S(O)2—Ra and C1-C8alkoxy-C1-C3alkyl-;
Ra is independently selected from the group consisting of hydrogen, C1-C8alkyl, C1-C3haloalkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C6cycloalkyl, heterocyclyl and phenyl wherein said heterocyclyl and phenyl groups are optionally substituted by one, two or three substituents independently selected from the group consisting of C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C2-C3alkenyl, C2-C3alkynyl, halogen, cyano and nitro;
Rb is selected from the group consisting of C1-C8alkyl, C1-C3haloalkyl, C2-C8alkenyl, C2-C8alkynyl, C3-C6 cycloalkyl, heterocyclyl and phenyl wherein said heterocyclyl and phenyl groups are optionally substituted by one, two or three substituents independently selected from the group consisting of C1-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C2-C3alkenyl, C2-C3alkynyl, halogen, cyano and nitro;
Rc is hydrogen or C1-C3 alkyl;
Rd is hydrogen or C1-C3 alkyl; and
n is independently 0, 1 or 2;
or an agriculturally acceptable salt thereof.