Herbicidal compounds

Patent metadata

Field	Value
Publication number	US-9402398-B2
Application number	US-201314386564-A
Country	US
Kind code	B2
Filing date	Mar 19, 2013
Priority date	Mar 20, 2012
Publication date	Aug 2, 2016
Grant date	Aug 2, 2016

Abstract

The present invention relates to compounds of Formula (I); or an agronomically acceptable salt of said compounds wherein A 1a , A 1b , A 2 , A 3 , A 4 , X, R 1 and R 2 are as defined herein. The invention further relates to herbicidal compositions which comprise a compound of Formula (I), and 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):

or an agronomically acceptable salt thereof,
wherein:
X is O or S;
A 1a and A 1b are independently selected from CH and N, wherein A 1a and A 1b are not both CH;
A 2 is N;
A 3 is CR 4 ;
A 4 is CR 5 ;
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 hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 3 alkoxy-C 1 -C 3 alkyl, C 1 -C 3 alkoxy-C 2 -C 3 alkoxy-C 1 -C 3 -alkyl, C 1 -C 3 haloalkoxy-C 1 -C 3 -alkyl, (C 1 -C 3 alkylsulfonyl-C 1 -C 3 alkylamino)-C 1 -C 3 alkyl, (C 1 -C 3 alkylsulfonyl-C 3 -C 4 cycloalkylamino)-C 1 -C 3 alkyl, C 1 -C 6 alkylcarbonyl-C 1 -C 3 alkyl, C 3 -C 6 cycloalkyl-C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 2 -C 6 -alkenyl, C 2 -C 6 -haloalkenyl, cyano-C 1 -C 6 -alkyl, arylcarbonyl-C 1 -C 3 -alkyl, aryl-C 1 -C 6 alkyl, aryloxy-C 1 -C 6 alkyl, wherein said aryl groups may be optionally substituted with one or more substituents from the group consisting of halogen, C 1 -C 3 -alkoxy, C 1 -C 3 -alkyl, C 1 -C 3 haloalkyl, and a three- to ten-membered mono- or bicyclic ring system, which may be aromatic, saturated or partially saturated and can contain from 1 to 4 heteroatoms each independently selected from the group consisting of nitrogen, oxygen and sulphur, the ring system being optionally substituted by one or more substituents selected from the group consisting of nitro, cyano, halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 2 -C 3 alkenyl, C 2 -C 3 alkynyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 6 alkyl-S(O)p- and C 1 -C 6 haloalkyl-S(O)p-;
R 4 is selected from the group consisting of hydrogen, hydroxyl, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy-C 1 -C 6 alkyl, C 1 -C 6 haloalkoxy-C 1 -C 6 alkyl, C 1 -C 6 alkoxy-C 1 -C 6 alkoxy-C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkoxy-C 2 -C 6 alkoxy, C 1 -C 6 alkylamino, C 1 -C 6 dialkylamino-, cyano, C 1 -C 6 alkyl-S(O)p- and C 1 -C 6 haloalkyl-S(O) p —;
R 5 is selected from the group consisting of hydrogen, hydroxyl, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl and C 1 -C 6 alkoxy-C 1 -C 3 alkyl; and
p=0, 1 or 2.

2. The compound according to claim 1 , wherein A 1a and A 1b are N and R 1 is methyl or ethyl.

3. The compound according to claim 1 , wherein R 2 is selected from the group consisting of C 1 -C 6 alkyl-, C 1 -C 3 alkoxy-C 1 -C 3 alkyl-, C 1 -C 3 haloalkoxy-C 1 -C 3 alkyl-, phenyl and a 5 or 6 membered heteroaromatic ring system containing from 1 to 4 heteroatoms each independently selected from the group consisting of nitrogen, oxygen and sulphur; the phenyl or 5 or 6 heteroaromatic ring system being optionally substituted by one or more substituents selected from the group consisting of nitro, cyano, halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 2 -C 3 alkenyl, C 2 -C 3 alkynyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 6 alkyl-S(O)p- and C 1 -C 6 haloalkyl-S(O)p-.

4. The compound according to claim 1 , wherein R 4 is selected from the group consisting of hydrogen, methyl and halogen.

5. The compound according to claim 1 , wherein R 5 is hydrogen.

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

7. The herbicidal composition according to claim 6 , further comprising at least one additional pesticide.

8. The herbicidal composition according to claim 7 , wherein the additional pesticide is a herbicide or herbicide safener.

9. A method of controlling weeds at a locus comprising application to the locus of a weed controlling amount of a composition according to claim 6 .

10. The compound of claim 2 , wherein R 2 is selected from the group consisting of C 1 -C 6 alkyl-, C 1 -C 3 alkoxy-C 1 -C 3 alkyl-, C 1 -C 3 haloalkoxy-C 1 -C 3 alkyl-, phenyl and a 5 or 6 membered heteroaromatic ring system containing from 1 to 4 heteroatoms each independently selected from the group consisting of nitrogen, oxygen and sulphur; the phenyl or 5 or 6 heteroaromatic ring system being optionally substituted by one or more substituents selected from the group consisting of nitro, cyano, halogen, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl, C 2 -C 3 alkenyl, C 2 -C 3 alkynyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkoxy, C 1 -C 6 alkyl -S(O)p- and C 1 -C 6 haloalkyl-S(O)p-.

11. The compound of claim 10 , wherein R 4 is selected from the group consisting of hydrogen, methyl and halogen.

12. The compound of claim 11 , wherein R 5 is hydrogen.

Assignees

• Syngenta Participations Ag
• Syngenta Ltd

Inventors

• Mitchell Glynn

Classifications

• A01N43/713 Primary

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

• C07D403/12 Primary

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

• C07D401/14

  containing three or more hetero rings · CPC title

• A01N43/653

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