Herbicidal compounds

Patent metadata

Field	Value
Publication number	US-12043599-B2
Application number	US-201916978922-A
Country	US
Kind code	B2
Filing date	Mar 6, 2019
Priority date	Mar 8, 2018
Publication date	Jul 23, 2024
Grant date	Jul 23, 2024

Abstract

The present invention relates to compounds of Formula (I), wherein R1, R2, R3, R4 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 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:

Assignees

• Syngenta Participations Ag

Inventors

• Hennessy Alan Joseph
• Jones Elizabeth Pearl
• Hachisu Shuji
• Willetts Nigel James
• Dale Suzanna
• Gregory Alexander William
• Houlsby Ian Thomas Tinmouth
• Bhonoah Yunas
• Comas-Barcelo Julia

Classifications

• C07D417/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D413/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D405/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D401/12

  linked by a chain containing hetero atoms as chain links · CPC title

• A01N43/42

  condensed with carbocyclic rings · CPC title