Herbicidal compounds

Patent metadata

Field	Value
Publication number	US-9701662-B2
Application number	US-201515120863-A
Country	US
Kind code	B2
Filing date	Feb 26, 2015
Priority date	Feb 27, 2014
Publication date	Jul 11, 2017
Grant date	Jul 11, 2017

Abstract

The present invention relates to compounds of Formula (I), or an agronomically acceptable salt of said compounds wherein A1, A2, R 1 , R 2 , R 3 and R 4 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, and to intermediates used to synthesize said compounds.

First claim

The invention claimed is:

1. A compound of Formula (I):

or an agronomically acceptable salt thereof,
wherein:
A 1 and A 2 are independently selected from CH and N, wherein A 1 and A 2 are not both CH;
R 1 is selected from the group consisting of C 1 -C 6 alkyl-, C 1 -C 6 haloalkyl- and C 1 -C 6 alkoxy-C 1 -C 3 alkyl-;
R 2 is selected from the group consisting of halogen, —NHR 5 and —O—R 6 ;
R 3 is selected from the group consisting of hydrogen, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl-, C 1 -C 6 alkoxy-C 1 -C 3 alkyl-, benzyl and phenyl, wherein the benzyl and phenyl are optionally substituted with one or more substituents selected from the group consisting of halogen, C 1 -C 6 alkyl, cyano, nitro, C 1 -C 6 haloalkyl-, C 1 -C 6 alkyl-S(O)p-, aryl-S(O)p-, C 1 -C 6 alkoxy- and C 1 -C 6 haloalkoxy-;
R 4 is selected from the group consisting of C 1 -C 6 alkyl, C 3 -C 6 -cycloalkyl and C 1 -C 6 haloalkyl-;
R 5 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 3 alkyl-, benzyl and phenyl, wherein the benzyl and phenyl groups are optionally substituted with one or more substituents selected from the group consisting of halogen, C 1 -C 6 alkyl-, cyano, nitro, C 1 -C 6 haloalkyl-, C 1 -C 6 alkyl-S(O)p-, aryl-S(O)p-, C 1 -C 6 alkoxy- and C 1 -C 6 haloalkoxy-;
R 6 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 3 alkyl; and
p=0, 1 or 2.

2. A compound according to claim 1 , wherein A 1 and A 2 are both N.

3. A compound according to claim 1 , wherein R 1 is selected from the group consisting of methyl, ethyl and propyl.

4. A compound according to claim 1 , wherein R 2 is selected from the group consisting of hydroxyl and —NHR 5 .

5. A compound according to claim 1 , wherein R 2 is chlorine.

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

7. A compound according to claim 1 , wherein R 3 is phenyl optionally substituted with one or more substituents selected from the group consisting of halogen, C 1 -C 6 alkyl, cyano, nitro, C 1 -C 6 haloalkyl-, C 1 -C 6 alkyl-S(O)p-, aryl-S(O)p-, C 1 -C 6 alkoxy- and C 1 -C 6 haloalkoxy-.

8. A compound according to claim 1 , wherein R 4 is methyl.

9. A compound according to claim 1 wherein R1 is methyl, ethyl or propyl; R2 is chlorine, hydroxyl, or —NHR 5 ; R3 is methyl or phenyl optionally substituted with one or more substituents selected from the group consisting of halogen, C 1 -C 6 alkyl, cyano, nitro, C 1 -C 6 haloalkyl-, C 1 -C 6 alkyl-S(O)p-, aryl-S(O)p-, C 1 -C 6 alkoxy- and C 1 -C 6 haloalkoxy-; and R4 is methyl.

10. A compound according to claim 1 wherein R1 is methyl, ethyl or propyl; R2 is chlorine; R3 is methyl; and R4 is methyl.

11. A compound according to claim 1 wherein R1 is methyl, ethyl or propyl; R2 is chlorine; R3 is phenyl optionally substituted with one or more substituents selected from the group consisting of halogen, C 1 -C 6 alkyl, cyano, nitro, C 1 -C 6 haloalkyl-, C 1 -C 6 alkyl-S(O)p-, aryl-S(O)p-, C 1 -C 6 alkoxy- and C 1 -C 6 haloalkoxy-; and R4 is methyl.

12. A herbicidal composition comprising a compound according to claim 1 and an agriculturally acceptable formulation adjuvant.

13. A herbicidal composition according to claim 12 , further comprising at least one additional pesticide.

14. A herbicidal composition according to claim 13 , wherein the additional pesticide is a herbicide.

15. A method of controlling weeds at a locus comprising application to the locus a weed controlling amount of the composition according to claim 12 .

Assignees

• Syngenta Participations Ag

Inventors

• Mitchell Glynn
• Mulholland Nicholas Phillip

Classifications

• A01N43/653

  1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles · CPC title

• C07D403/12 Primary

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

• A01N43/713

  having rings with four or more nitrogen atoms as the only ring hetero atoms · CPC title