IP Library Granted Patent US 12,043,599
Granted Patent B2
US 12,043,599 · App. 16/978,922 · Granted Jul 23, 2024

Herbicidal compounds

Inventors: 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); Julia Comas-Barcelo (Bracknell, GB)
Assignee: SYNGENTA PARTICIPATIONS AG
C07D221/20A01N25/32A01N43/42C07D401/12C07D405/12C07D413/12C07D417/12
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Quick Facts
Patent No.
US 12,043,599
App. No.
16/978,922
Granted
Jul 23, 2024
Kind
B2
Abstract

The present invention relates to compounds of Formula (I), wherein R 1 , R 2 , R 3 , R 4 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.

Claims (42)

1. A compound of Formula (I)

wherein

R 1 is methyl;

R 2 is methyl or methoxy;

R 3 is methyl or methoxy;

R 4 is selected from the group consisting of —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 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)(CR 9 R 10 ) 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, —(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 contains 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 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—CH 2 —; and

X is selected from the group consisting of O, S and N—R 14 ;

R 14 is selected from the group consisting of hydrogen, C 1 -C 3 alkyl and C 1 -C 3 alkoxy-;

each n is independently 0, 1 or 2;

G is selected from the group consisting of hydrogen, —(CH 2 ) n —R a , —C(O)—R a , —C(O)—(CR c R d ) n —O—R b , —C(O)—(CR c R d ) n —S—R b , —C(O)NR a R a , —S(O) 2 —R a and C 1 -C 8 alkoxy-C 1 -C 3 alkyl-;

R a is independently selected from the group consisting of hydrogen, C 1 -C 8 alkyl, C 1 -c 3 haloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 3 -C 6 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 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 b is selected from the group consisting of C 1 -C 8 alkyl, C 1 -C 3 haloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, C 3 -C 6 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 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 c is hydrogen or C 1 -C 3 alkyl; and

R d is hydrogen or C 1 -C 3 alkyl;

or an agriculturally acceptable salt thereof.

2. The compound according to claim 1 , wherein R 2 is methyl.

3. The compound according to claim 1 , wherein R 3 is methyl.

4. The compound according to claim 1 , wherein R 3 is methoxy.

5. The compound according to claim 1 , wherein R 4 is —C(O)NR 5 R 6 .

6. The compound according to claim 1 , wherein R 4 is —C(O)NR 7 C(O)R 8 .

7. The compound according to claim 1 , wherein G is hydrogen.

8. The compound according to claim 1 , wherein G is —C(O)C 1 -C 6 alkyl.

9. The compound according to claim 1 , wherein G is —C(O)—O—C 1 -C 6 alkyl.

10. An herbicidal composition comprising a compound of Formula (I) according to claim 1 and an agriculturally acceptable formulation adjuvant.

11. The herbicidal composition according to claim 10 , further comprising at least one additional pesticide.

12. The herbicidal composition according to claim 11 , wherein the additional pesticide is an herbicide or herbicide safener.

13. A method of controlling weeds at a locus comprising applying to the locus of the weeds, the weed controlling amount of a composition according to claim 10 .

14. A method of controlling a weed, comprising: applying a weed control ling amount of a composition according to claim 10 to the weed.

15. A compound selected from:

16. A compound selected from:

Assignments (2)
MERGER AND CHANGE OF NAME Recorded Feb 28, 2025
From: SYNGENTA PARTICIPATIONS AG; SYNGENTA PARTICIPATIONS AG
To: SYNGENTA CROP PROTECTION AG
Reel/Frame 070362/0665 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 30, 2020
From: HENNESSY, ALAN JOSEPH; JONES, ELIZABETH PEARL; HACHISU, SHUJI; WILLETTS, NIGEL JAMES; DALE, SUZANNA JANE; GREGORY, ALEXANDER WILLIAM; HOULSBY, IAN THOMAS TINMOUTH; BHONOAH, YUNAS; COMAS-BARCELO, JULIA
To: SYNGENTA PARTICIPATIONS AG
Reel/Frame 054224/0305 →
Priority Claims (1)
GB 1803736 · Mar 8, 2018 · national
Continuity (1)
Related Publication 20210047274A1 · Feb 18, 2021
Cited By (1)
US 12,590,067