Cyclic diones as herbicidal compounds

Patent metadata

Field	Value
Publication number	US-12319640-B2
Application number	US-202017631052-A
Country	US
Kind code	B2
Filing date	Jul 27, 2020
Priority date	Jul 31, 2019
Publication date	Jun 3, 2025
Grant date	Jun 3, 2025

Abstract

The present invention relates to compounds of Formula (I), wherein R 1 , R 2 , R 3 , R 4x , R 4y , m, n and G are as defined herein. The invention further relates to herbicidal compositions which comprise a compound of Formula (I), to their use for controlling weeds, in particular in crops of useful plants.

First claim

The invention claimed is:

1. A compound of Formula (I)

wherein
R 1 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 R 15 substituents;
R 2 is methyl, ethyl, methoxy or chloro;
R 3 is selected from the group consisting of methyl, ethyl, methoxy and chloro;
m is 0 or 1;
n is 0 or 1;
R 4x is selected from the group consisting of hydrogen, C 1 -C 6 alkyl, hydroxyl, methoxy and halogen;
R 4y is selected from the group consisting of R4 a , R4 b and R4 c :

R 4aa is selected from the group consisting of hydrogen, C 1 -C 6 alkyl and C 1 -C 6 alkoxy-;
R 4ab is selected from the group consisting of hydrogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, hydroxy-, hydroxyC 1 -C 6 alkyl-, C 1 -C 6 alkoxy, C 3 -C 6 cycloalkyl, —C 1 -C 4 alkoxyC 1 -C 6 alkyl, —C 1 -C 3 alkoxyC 1 -C 6 haloalkyl, cyanoC 1 -C 6 alkyl-, C(O)R 27 , S(O) n R 27 , phenyl, -pyridyl, wherein the phenyl and pyridyl are optionally substituted by one, two or three substituents independently selected from the group consisting of C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 2 -C 3 alkenyl, C 2 -C 3 alkynyl, halogen, cyano and nitro; or
R 4aa and R 4ab together form —(CH 2 ) q —, —CH 2 CH 2 X 1 CH 2 CH 2 — or —C(O)CH 2 X 1 CH 2 CH 2 — wherein X 1 is selected from the group consisting of O, S(O) n and N—R 28 ; and
R 4ba is selected from the group consisting of hydrogen, C 1 -C 4 alkyl and C 1 -C 4 alkoxy-;
R 4bb is selected from the group consisting of C 1 -C 4 alkyl, C 1 -C 4 alkoxy-, C 1 -C 4 haloalkyl, —C(O)C 1 -C 4 alkyl, —C(O)C 1 -C 4 haloalkyl, hydroxyC 1 -C 6 alkyl-C(O)—, —S(O) n C 1 -C 6 alkyl, —S(O) n C 1 -C 6 haloalkyl, —S(O) n —(CH 2 ) n —C 3 -C 6 cycloalkyl, —S(O) n C(R 11 )R 12 R 13 , —C(O)H, —C(O)—(CH 2 ) n —C 3 -C 6 cycloalkyl, —C(O)C(R 11 )R 12 R 13 , —C(O)C 2 -C 4 alkenyl, —C(O)(CR 9 R 10 )CN, —C(O)(CR 9 R 10 )(CR 9 R 10 )CN, —C(O)CH 2 C(O)—C 1 -C 6 alkyl, —C(O)CH 2 OC(O)—C 1 -C 6 alkyl, —C(O)OC 1 -C 6 alkyl, —C(O)OC 1 -C 6 haloalkyl, —C(O)(CH 2 ) n S(O) n C 1 -C 6 alkyl, —C(O)C 1 -C 3 alkoxyC 1 -C 6 alkyl, —C(O)C 1 -C 3 alkoxyC 2 -C 6 alkenyl, —C(O)C 1 -C 3 alkoxyC 2 -C 6 alkynyl, —C(O)C 1 -C 3 alkoxyC 1 -C 6 haloalkyl, —C(O)C 1 -C 3 alkoxyC 3 -C 6 cycloalkyl, —C(O)OC 1 -C 3 alkoxyC 1 -C 6 alkyl, —C(O)C 1 -C 3 alkoxyC 1 -C 3 alkoxyC 1 -C 6 alkyl, —C(O)(CH 2 ) n NR 5 R 6 , —C(O)—(CH 2 ) n —NR 7 C(O)R 8 , —C(O)—(CH 2 ) n —O—N═CR 5 R 5 , —CN, —S(O) 2 NR 16 R 17 , —S(O)(═NR 18 )R 19 , —C(O)C(O)R 20 , —C(O)C(R 23 )═N—O—R 24 or —C(O)C(R 23 )═N—NR 25 R 26 , —(CH 2 ) n -phenyl, —C(O)—(CH 2 ) n -phenyl, —S(O) n —(CH 2 ) n —phenyl, -heterocyclyl, —C(O)—(CH 2 ) n -heterocyclyl, —C(O)(CH 2 ) n O—(CH 2 ) n -heterocyclyl, —S(O) n —(CH 2 ) 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 C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 2 -C 3 alkenyl, C 2 -C 3 alkynyl, halogen, cyano and nitro;
R 5 is independently selected from the group consisting of hydrogen and C 1 -C 6 alkyl;
R 6 is selected from the group consisting of hydrogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 haloalkyl, hydroxyl-, C 1 -C 6 alkoxy, C 3 -C 6 cycloalkyl, —C 1 -C 4 alkoxyC 1 -C 6 alkyl, —C 1 -C 3 alkoxyC 1 -C 6 haloalkyl, —(CR 9 R 10 )C 1 -C 6 haloalkyl, —(CR 9 R 10 )C(O)NR 5 R 5 , phenyl, -pyridyl, wherein the phenyl and pyridyl are optionally substituted by one, two or three substituents independently selected from the group consisting of C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 2 -C 3 alkenyl, C 2 -C 3 alkynyl, halogen, cyano and nitro; or
R 5 and R 6 together form —CH 2 CH 2 OCH 2 CH 2 —; and
R 7 is selected from the group consisting of hydrogen and C 1 -C 6 alkyl;
R 8 is selected from the group consisting of hydrogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 3 -C 6 cycloalkyl, phenyl, -pyridyl, wherein the phenyl and pyridyl are optionally substituted by one, two or three substituents independently selected from the group consisting of C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 2 -C 3 alkenyl, C 2 -C 3 alkynyl, halogen, cyano and nitro;
R 9 is hydrogen or methyl;
R 10 is hydrogen or methyl; or
R 9 and R 10 together form —CH 2 CH 2 —; and
R 11 is hydrogen or methyl;
R 12 is selected from the group consisting of hydrogen, C 1 -C 6 alkyl, hydroxyl and C 1 -C 6 alkoxy-;
R 13 is selected from the group consisting of hydrogen, C 1 -C 6 alkyl, hydroxyl and C 1 -C 6 alkoxy; or
R 12 and R 13 together form —CH 2 —X 2 —CH 2 — wherein X 2 is selected from the group consisting of O, S and N—R 14 ; and
R 14 is selected from the group consisting of hydrogen, C 1 -C 3 alkyl and C 1 -C 3 alkoxy-;
R 15 is independently selected from the group consisting of C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, cyano and halogen;
R 16 is hydrogen or C 1 -C 6 alkyl; and
R 17 is selected from the group consisting of hydrogen, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkoxy-C 1 -C 3 alkyl-, —C(O)C 1 -C 6 alkyl, —C(O)OC 1 -C 6 alkyl and CH 2 CN; or
R 16 and R 17 together form —CH 2 CH 2 OCH 2 CH 2 —, —CH 2 CH 2 S(O) 2 CH 2 CH 2 —; and
R 18 is hydrogen or C 1 -C 6 alkyl;
R 19 is selected from the group consisting of hydrogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 3 -C 6 cycloalkyl, phenyl, -pyridyl, wherein the phenyl and pyridyl are optionally substituted by one, two or three substituents independently selected from the group consisting of C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 2 -C 3 alkenyl, C 2 -C 3 alkynyl, halogen, cyano and nitro;
R 20 is selected from the group consisting of C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy-, C 1 -C 6 haloalkoxy, —NR 21 R 22 , phenyl and -pyridyl, wherein the phenyl and pyridyl are optionally substituted by one, two or three substituents independently selected from the group consisting of C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 2 -C 3 alkenyl, C 2 -C 3 alkynyl, halogen, cyano and nitro;
R 21 is selected from the group consisting of hydrogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkoxyC 1 -C 3 alkyl-, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl- and C 1 -C 6 haloalkoxy-, —C(O)C 1 -C 6 alkyl, phenyl, -pyridyl, wherein the phenyl and pyridyl are optionally substituted by one, two or three substituents independently selected from the group consisting of C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 1 -C 3 alkoxy, C 2 -C 3 alkenyl, C 2 -C 3 alkynyl, halogen, cyano and nitro;
R 22 is hydrogen or C 1 -C 6 alkyl; or
R 21 and R 22 together form —CH 2 CH 2 OCH 2 CH 2 —; and
R 23 is selected from the group consisting of hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy- and C 1 -C 6 haloalkoxy-;
R 24 is selected from the group consisting of hydrogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxyC 1 -C 3 alkyl-, C 3 -C 6 cycloalkyl, —CH 2 CN, tetrahydropyranyl-, phenyl and -pyridyl, wherein the phenyl and pyridyl are

Assignees

• Syngenta Crop Protection Ag

Inventors

• Hennessy Alan Joseph
• Jones Elizabeth Pearl
• Dale Suzanna Jane
• Gregory Alexander William
• Houlsby Ian Thomas Tinmouth
• Bhonoah Yunas
• Comas-Barcelo Julia
• Elves Philip Michael

Classifications

• C07D319/12

  not condensed with other rings · CPC title

• C07D305/08

  with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring atoms · CPC title

• C07D279/12

  not condensed with other rings · CPC title

• C07D265/30

  not condensed with other rings · CPC title

• C07D263/34

  with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms · CPC title