US 12,479,804 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. 17/627,341
Filed by SYNGENTA CROP PROTECTION AG, Basel (CH)
PCT Filed Jul. 15, 2020, PCT No. PCT/EP2020/070007
§ 371(c)(1), (2) Date Jan. 14, 2022,
PCT Pub. No. WO2021/009232, PCT Pub. Date Jan. 21, 2021.
Claims priority of application No. 1910168 (GB), filed on Jul. 16, 2019.
Prior Publication US 2022/0259153 A1, Aug. 18, 2022
Int. Cl. C07D 221/20 (2006.01); A01N 43/38 (2006.01); A01N 43/42 (2006.01); A01N 43/44 (2006.01); A01N 43/46 (2006.01); A01N 43/72 (2006.01); A01N 43/76 (2006.01); A01N 43/82 (2006.01); A01N 43/84 (2006.01); A01N 43/86 (2006.01); A01N 43/90 (2006.01); A01P 13/00 (2006.01); C07D 205/12 (2006.01); C07D 209/54 (2006.01); C07D 223/14 (2006.01); C07D 225/00 (2006.01); C07D 265/02 (2006.01); C07D 265/36 (2006.01); C07D 279/02 (2006.01); C07D 401/06 (2006.01); C07D 401/12 (2006.01); C07D 471/04 (2006.01); C07D 498/00 (2006.01); C07D 498/04 (2006.01)
CPC C07D 221/20 (2013.01) [A01N 43/38 (2013.01); A01N 43/42 (2013.01); A01N 43/44 (2013.01); A01N 43/46 (2013.01); A01N 43/72 (2013.01); A01N 43/76 (2013.01); A01N 43/82 (2013.01); A01N 43/84 (2013.01); A01N 43/86 (2013.01); A01N 43/90 (2013.01); A01P 13/00 (2021.08); C07D 205/12 (2013.01); C07D 209/54 (2013.01); C07D 223/14 (2013.01); C07D 225/00 (2013.01); C07D 265/02 (2013.01); C07D 265/36 (2013.01); C07D 279/02 (2013.01); C07D 401/06 (2013.01); C07D 401/12 (2013.01); C07D 471/04 (2013.01); C07D 498/00 (2013.01); C07D 498/04 (2013.01)] 14 Claims
 
1. A compound of Formula (I)

OG Complex Work Unit Chemistry
wherein
R1 is 1-propynyl,
R2 is methyl;
R3 is methyl;
R4 is selected from the group consisting of D4, D5, D6, D12, D13, D14, D23, D28 and D30:

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry

OG Complex Work Unit Chemistry
Y is selected from the group consisting of O, CR27R28 and N-R29;
R4c is selected from the group consisting of hydrogen, 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, —S(O)2NR16R17S(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)nheterocyclyl, —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-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
R11 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-;
R16 is hydrogen or C1-C6alkyl; and
R17 is selected from the group consisting of hydrogen, C1-C6alkyl, C3-C6 cycloalkyl, 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—;
R18 is hydrogen or C1-C6alkyl;
R19 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;
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-CoalkoxyC1-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—;
R23 is selected from the group consisting of hydrogen, C1-C6alkyl, C1-C6haloalkyl, C1-C6 alkoxy- and C1-C6haloalkoxy-;
R24 is selected from the group consisting of hydrogen, C1-C6alkyl, C1-C6alkoxyC1-C3alkyl-, C3-C6 cycloalkyl, —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;
R27 is hydrogen or C1-C4alkyl;
R28 is hydrogen or C1-C4alkyl;
R29 is selected from the group consisting of hydrogen, C1-C4alkyl, C1-C4alkoxy-, C1-C4haloalkyl, —C(═O)C1-C4alkyl, —C(═O)C1-C4haloalkyl; and
G is selected from the group consisting of hydrogen, —(CH2)n—Ra, —C(O)—Ra, —C(O)—(CRcR4)n—O—Rb, —C(O)—(CRcR4)n—S—Rb, —C(O) NRaRa, —S(O)2—Ra and C1-C3alkoxy-C1-C3alkyl-;
Ra is independently selected from the group consisting of hydrogen, C1-C3alkyl, C1-C3haloalkyl, C2-C3alkenyl, C2-C3alkynyl, 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-C3alkyl, C1-C3haloalkyl, C2-C3alkenyl, 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.