Herbicidal compounds

Patent metadata

Field	Value
Publication number	US-12281081-B2
Application number	US-202017429516-A
Country	US
Kind code	B2
Filing date	Feb 10, 2020
Priority date	Feb 11, 2019
Publication date	Apr 22, 2025
Grant date	Apr 22, 2025

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 selected from the group consisting of methyl, ethynyl, 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 9 substituents;
R 2 is selected from the group consisting of methyl, ethyl, methoxy and chloro;
R 3 is selected from the group consisting of methyl, ethyl, methoxy and chloro;
R 4 is —S(O) 2 NR 5 R 6 or —S(O)(═NR 7 )R 8 ;
R 5 is hydrogen or C 1 -C 6 alkyl; and
R 6 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 5 and R 6 together form —CH 2 CH 2 OCH 2 CH 2 —, —CH 2 CH 2 S(O) 2 CH 2 CH 2 —; and
R 7 is hydrogen or 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 independently selected from the group consisting of C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, cyano and halogen;
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;
R d is hydrogen or C 1 -C 3 alkyl; and
n is independently 0, 1 or 2;
or an agriculturally acceptable salt thereof.

2. The compound of according to claim 1 , wherein R 1 is 1-propynyl, R 2 is methyl or methoxy and R 3 is methyl or methoxy.

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

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

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

6. The compound according to claim 1 , wherein R 4 is —S(O) 2 NR 5 R 6 .

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

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

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

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

11. A herbicidal composition comprising the compound of Formula (I) according to claim 1 and an agriculturally acceptable formulation adjuvant.

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

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

14. A method of controlling weeds, at a locus comprising applying to the locus of the weeds a weed controlling amount of the composition according to claim 11 .

15. A compound, or an agriculturally acceptable salt thereof, selected from the group consisting of:

16. A compound, or an agriculturally acceptable salt thereof, selected from the group consisting of:

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

Classifications

• A01N43/84

  six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4 · CPC title

• A01N43/42

  condensed with carbocyclic rings · CPC title

• A01N25/32

  Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions · CPC title

• A01P13/00

  Herbicides; Algicides · CPC title

• C07D411/12

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