US 12,250,947 B2
Substituted azaspiro-cycles as herbicides
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. 17/429,504
Filed by SYNGENTA CROP PROTECTION AG, Basel (CH)
PCT Filed Feb. 12, 2020, PCT No. PCT/EP2020/053569
§ 371(c)(1), (2) Date Aug. 9, 2021,
PCT Pub. No. WO2020/165233, PCT Pub. Date Aug. 20, 2020.
Claims priority of application No. 1901961 (GB), filed on Feb. 13, 2019.
Prior Publication US 2022/0117228 A1, Apr. 21, 2022
Int. Cl. A01N 43/42 (2006.01); A01N 43/84 (2006.01); A01P 13/00 (2006.01); C07D 221/20 (2006.01); C07D 401/10 (2006.01); C07D 401/12 (2006.01)
CPC A01N 43/42 (2013.01) [A01N 43/84 (2013.01); A01P 13/00 (2021.08); C07D 221/20 (2013.01); C07D 401/10 (2013.01); C07D 401/12 (2013.01)] 15 Claims
 
1. A compound of Formula (I)

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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 R8 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 —C(O)C(O)R5;
R5 is selected from the group consisting of C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy-, C1-C6haloalkoxy, —NR6R7, phenyl and-pyridyl, wherein the phenyl and pyridyl are optionally substituted by one, two or three substituents independently selected from the group consisting of C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C2-C3 alkenyl, C2-C3 alkynyl, halogen, cyano and nitro;
R6 is selected from the group consisting of hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C1-C6alkoxyC1-C3alkyl-, C3-C6 cycloalkyl, C1-C6haloalkyl- and C1-C6haloalkoxy-, —C(O)C1-C6alkyl, phenyl, -pyridyl, wherein the phenyl and pyridyl are optionally substituted by one, two or three substituents independently selected from the group consisting of C1-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C2-C3 alkenyl, C2-C3 alkynyl, halogen, cyano and nitro;
R7 is hydrogen or C1-C6alkyl; or
R6 and R7 together form —CH2CH2OCH2CHD2—; and
R8 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-C8alkyl, C1-C3haloalkyl, C1-C3alkoxy, C2-C3alkenyl, C2-C3alkynyl, halogen, cyano and nitro;
Rb is selected from the group consisting of C1-C3alkyl, C1-C3haloalkyl, C2-C8alkenyl, C2-C3alkynyl, 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.
 
15. A compound selected from the group consisting of:

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