US 12,319,640 B2
Cyclic diones as 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); Julia Comas-Barcelo, Bracknell (GB); and Philip Michael Elves, Bracknell (GB)
Assigned to SYNGENTA CROP PROTECTION AG, Basel (CH)
Appl. No. 17/631,052
Filed by SYNGENTA CROP PROTECTION AG, Basel (CH)
PCT Filed Jul. 27, 2020, PCT No. PCT/EP2020/071131
§ 371(c)(1), (2) Date Jan. 28, 2022,
PCT Pub. No. WO2021/018834, PCT Pub. Date Feb. 4, 2021.
Claims priority of application No. 1910926 (GB), filed on Jul. 31, 2019.
Prior Publication US 2022/0281804 A1, Sep. 8, 2022
Int. Cl. C07D 213/81 (2006.01); A01N 37/18 (2006.01); A01N 37/36 (2006.01); A01N 37/42 (2006.01); A01N 37/44 (2006.01); A01N 41/06 (2006.01); A01N 43/20 (2006.01); A01N 43/40 (2006.01); A01N 43/54 (2006.01); A01N 43/58 (2006.01); A01N 43/60 (2006.01); A01N 43/76 (2006.01); A01N 43/84 (2006.01); A01N 47/06 (2006.01); C07C 233/32 (2006.01); C07C 233/56 (2006.01); C07C 233/61 (2006.01); C07C 233/76 (2006.01); C07C 235/14 (2006.01); C07C 237/24 (2006.01); C07C 255/19 (2006.01); C07C 255/29 (2006.01); C07C 259/08 (2006.01); C07C 275/26 (2006.01); C07C 275/50 (2006.01); C07C 311/07 (2006.01); C07C 311/14 (2006.01); C07D 213/61 (2006.01); C07D 213/75 (2006.01); C07D 213/85 (2006.01); C07D 237/24 (2006.01); C07D 239/30 (2006.01); C07D 241/24 (2006.01); C07D 263/34 (2006.01); C07D 265/30 (2006.01); C07D 279/12 (2006.01); C07D 305/08 (2006.01); C07D 311/14 (2006.01); C07D 319/12 (2006.01)
CPC C07C 233/32 (2013.01) [A01N 37/18 (2013.01); A01N 37/36 (2013.01); A01N 37/42 (2013.01); A01N 37/44 (2013.01); A01N 41/06 (2013.01); A01N 43/20 (2013.01); A01N 43/40 (2013.01); A01N 43/54 (2013.01); A01N 43/58 (2013.01); A01N 43/60 (2013.01); A01N 43/76 (2013.01); A01N 43/84 (2013.01); A01N 47/06 (2013.01); C07C 233/56 (2013.01); C07C 233/61 (2013.01); C07C 233/76 (2013.01); C07C 235/14 (2013.01); C07C 237/24 (2013.01); C07C 255/19 (2013.01); C07C 255/29 (2013.01); C07C 259/08 (2013.01); C07C 275/26 (2013.01); C07C 275/50 (2013.01); C07C 311/07 (2013.01); C07C 311/14 (2013.01); C07D 213/61 (2013.01); C07D 213/75 (2013.01); C07D 213/81 (2013.01); C07D 213/85 (2013.01); C07D 237/24 (2013.01); C07D 239/30 (2013.01); C07D 241/24 (2013.01); C07D 263/34 (2013.01); C07D 265/30 (2013.01); C07D 279/12 (2013.01); C07D 305/08 (2013.01); C07D 319/12 (2013.01)] 20 Claims
 
1. A compound of Formula (I)

OG Complex Work Unit Chemistry
wherein
R1 is selected from the group consisting of 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 R15 substituents;
R2 is methyl, ethyl, methoxy or chloro;
R3 is selected from the group consisting of methyl, ethyl, methoxy and chloro;
m is 0 or 1;
n is 0 or 1;
R4x is selected from the group consisting of hydrogen, C1-C6 alkyl, hydroxyl, methoxy and halogen;
R4y is selected from the group consisting of R4a, R4b and R4c:

OG Complex Work Unit Chemistry
R4aa is selected from the group consisting of hydrogen, C1-C6 alkyl and C1-C6alkoxy-;
R4ab is selected from the group consisting of hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6haloalkyl, hydroxy-, hydroxyC1-C6alkyl-, C1-C6alkoxy, C3-C6cycloalkyl, —C1-C4alkoxyC1-C6alkyl, —C1-C3alkoxyC1-C6haloalkyl, cyanoC1-C6alkyl-, C(O)R27, S(O)nR27, 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
R4aa and R4ab together form —(CH2)q—, —CH2CH2X1CH2CH2— or —C(O)CH2X1CH2CH2— wherein X1 is selected from the group consisting of O, S(O)n and N—R28; and
R4ba is selected from the group consisting of hydrogen, C1-C4 alkyl and C1-C4alkoxy-;
R4bb is selected from the group consisting of C1-C4alkyl, C1-C4alkoxy-, C1-C4haloalkyl, —C(O)C1-C4alkyl, —C(O)C1-C4haloalkyl, hydroxyC1-C6alkyl-C(O)—, —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, —S(O)2NR16R17, —S(O)(═NR18)R19, —C(O)C(O)R20, —C(O)C(R23)═N—O—R24 or —C(O)C(R23)═N—NR25R26, —(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 independently 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-C6alkoxy, 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—X2—CH2— wherein X2 is selected from the group consisting of O, S and N—R14; and
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;
R16 is hydrogen or C1-C6alkyl; and
R17 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
R16 and R17 together form —CH2CH2OCH2CH2—, —CH2CH2S(O)2CH2CH2—; and
R18 is hydrogen or C1-C6alkyl;
R19 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-C3 alkyl, C1-C3 haloalkyl, C1-C3 alkoxy, C2-C3 alkenyl, C2-C3 alkynyl, halogen, cyano and nitro;
R20 is selected from the group consisting of C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy-, C1-C6haloalkoxy, —NR21R22, 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;
R21 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;
R22 is hydrogen or C1-C6alkyl; or
R21 and R22 together form —CH2CH2OCH2CH2—; and
R23 is selected from the group consisting of hydrogen, C1-C6alkyl, C1-C6haloalkyl, C1-C6alkoxy- and C1-C6haloalkoxy-;
R24 is selected from the group consisting of hydrogen, C1-C6alkyl, C1-C6alkoxyC1-C3alkyl-, C3-C6cycloalkyl, —CH2CN, tetrahydropyranyl-, 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-C3alkyl, C1-C3haloalkyl, C1-C3alkoxy, C2-C3alkenyl, C2-C3alkynyl, halogen, cyano and nitro;
R25 is hydrogen or C1-C6 alkyl;
R26 is hydrogen or C1-C6 alkyl; and
R4ca is selected from hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, C1-C6haloalkyl, hydroxyl-, C1-C6alkoxy, C3-C6cycloalkyl, —C1-C4alkoxyC1-C6alkyl, —C1-C3alkoxyC1-C6haloalkyl, cyanoC1-C6alkyl-, C(O)R27, S(O)nR27, 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;
R4cb is selected from the group consisting of hydrogen, C1-C6 alkyl and C1-C6alkoxy-; or
R4ca and R4cb together form —(CH2)q—, —CH2CH2X1CH2CH2— or —C(O)CH2X1CH2CH2— wherein X1 is selected from the group consisting of O, S(O)n and N—R28;
R27 is selected from the group consisting of hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6alkenyl, C2-C6alkynyl, 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;
R28 is selected from the group consisting of hydrogen, C1-C3 alkyl, —C(O)C1-C3alkyl and C1-C3 alkoxy-;
q is 3, 4 or 5; and
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.