US 11,980,188 B2
Spiro cyclohexanedione derivates as herbicides
Alan Joseph Hennessy, Bracknell (GB); Elizabeth Pearl Jones, Bracknell (GB); Shuji Hachisu, Bracknell (GB); Nigel James Willetts, Bracknell (GB); Suzanna 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 PARTICIPATIONS AG, Basel (CH)
Appl. No. 16/979,589
Filed by SYNGENTA PARTICIPATIONS AG, Basel (CH)
PCT Filed Mar. 11, 2019, PCT No. PCT/EP2019/056049
§ 371(c)(1), (2) Date Sep. 10, 2020,
PCT Pub. No. WO2019/175117, PCT Pub. Date Sep. 19, 2019.
Claims priority of application No. 1804002 (GB), filed on Mar. 13, 2018.
Prior Publication US 2021/0000113 A1, Jan. 7, 2021
This patent is subject to a terminal disclaimer.
Int. Cl. A01N 43/54 (2006.01); A01N 25/02 (2006.01); A01N 43/42 (2006.01); A01N 43/56 (2006.01); C07D 221/20 (2006.01); C07D 401/10 (2006.01); C07D 401/14 (2006.01); C07D 405/06 (2006.01)
CPC A01N 43/54 (2013.01) [A01N 25/02 (2013.01); A01N 43/42 (2013.01); A01N 43/56 (2013.01); C07D 221/20 (2013.01); C07D 401/10 (2013.01); C07D 401/14 (2013.01); C07D 405/06 (2013.01)] 15 Claims
 
1. A compound of Formula (I)

OG Complex Work Unit Chemistry
wherein
R1 is selected from methyl, 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 R15 substituents;
R2 is methyl or methoxy;
R3 is methyl or methoxy;
R4 is selected from the group consisting of C1-C4alkyl, C1-C4alkoxy-, C1-C4haloalkyl, —C(═O)C1-C4alkyl, —C(═O)C1-C4haloalkyl, —S(O)nC1-C6alkyl, —S(O)nC1-C6haloalkyl, —S(O)n—(CH2)n—C3-C6cycloalkyl, —S(O)nC(R11)R12R13, —C(O)H, —C(O)—(CH2)n—C3-C6cycloalkyl, —C(O)C(R11)R12R13, —C(O)C2-C4alkenyl, —C(O)(CR9R10)CN, —C(O)(CR9R10)(CR9R10)CN, —C(O)CH2C(O)—C1-C6alkyl, —C(O)CH2OC(O)—C1-C6alkyl, —C(O)OC1-C6alkyl, —C(O)OC1-C6haloalkyl, —C(O)(CH2)nS(O)nC1-C6alkyl, —C(O)C1-C3alkoxyC1-C6alkyl, —C(O)C1-C3alkoxyC2-C6alkenyl, —C(O)C1-C3alkoxyC2-C6alkynyl, —C(O)C1-C3alkoxyC1-C6haloalkyl, —C(O)C1-C3alkoxyC3-C6cycloalkyl, —C(O)OC1-C3alkoxyC1-C6alkyl, —C(O)C1-C3alkoxyC1-C3alkoxyC1-C6alkyl, —C(O)(CH2)nNR5R6, —C(O)—(CH2)n—NR7C(O)R8, —C(O)—(CH2)n—O—N═CR5R5, —CN, —(CH2)n-phenyl, —C(O)—(CH2)n-phenyl, —S(O)n—(CH2)n-phenyl, -heterocyclyl, —C(O)—(CH2)n-heterocyclyl, —C(O)(CH2)nO—(CH2)n-heterocyclyl, —S(O)n—(CH2)n-heterocyclyl, wherein each heterocyclyl is a 5- or 6-membered heterocyclyl which may be aromatic, saturated or partially saturated and can contain from 1 to 4 heteroatoms each independently selected from the group consisting of oxygen, nitrogen and sulphur, and wherein said heterocyclyl or 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;
R5 is selected from the group consisting of hydrogen and C1-C6 alkyl;
R6 is selected from the group consisting of hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6haloalkyl, hydroxyl-, C1-C6 alkoxy, C3-C6 cycloalkyl, —C1-C4alkoxyC1-C6alkyl, —C1-C3alkoxyC1-C6haloalkyl, —(CR9R10)C1-C6haloalkyl, —(CR9R10)C(O)NR5R5, 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; or
R5 and R6 together form —CH2CH2OCH2CH2—; and
R7 is selected from the group consisting of hydrogen and C1-C6 alkyl;
R8 is selected from the group consisting of hydrogen, C1-C6 alkyl, C1-C6 alkoxy, C3-C6 cycloalkyl, 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;
R9 is hydrogen or methyl;
R10 is hydrogen or methyl; or
R9 and R10 together form —CH2CH2—; and
R11 is hydrogen or methyl;
R12 is selected from the group consisting of hydrogen, C1-C6 alkyl, hydroxyl and C1-C6 alkoxy-;
R13 is selected from the group consisting of hydrogen, C1-C6 alkyl, hydroxyl and C1-C6 alkoxy; or
R12 and R13 together form —CH2—X—CH2—; and
X is selected from the group consisting of O, S and N—R14;
R14 is selected from the group consisting of hydrogen, C1-C3 alkyl and C1-C3 alkoxy-;
R15 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.