Substituted azaspiro-cycles as herbicides

Patent metadata

Field	Value
Publication number	US-2022117228-A1
Application number	US-202017429504-A
Country	US
Kind code	A1
Filing date	Feb 12, 2020
Priority date	Feb 13, 2019
Publication date	Apr 21, 2022
Grant date	—

Abstract

The present invention relates to compounds of Formula (I), (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.

First claim

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 8 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 —C(O)C(O)R 5 ;
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 6 haloalkoxy, —NR 6 R 7 , phenyl and -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 6 is selected from the group consisting of hydrogen, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 1 -C 6 alkoxyC 1 -C 3 alkyl-, C 3 -C 6 cycloalkyl, C 1 -C 6 haloalkyl- and C 1 -C 6 haloalkoxy-, —C(O)C 1 -C 6 alkyl, 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 7 is hydrogen or C 1 -C 6 alkyl; or
R 6 and R 7 together form —CH 2 CH 2 OCH 2 CH 2 —; and
R 8 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′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 . A compound according to claim 1 , wherein R 1 is 1-propynyl, R 2 is methyl or methoxy and R 3 is methyl or methoxy.

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

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

5 . A compound according to claim 1 , wherein R 5 is selected from the group consisting of methyl, ethyl, t-butyl, trifluoromethyl and ethoxy.

6 . A compound according to claim 1 , wherein R 5 is —NR 6 R 7 .

7 . A compound according to claim 6 , wherein R 6 is selected from the group consisting hydrogen, methyl, t-butyl and pyridyl, and R 7 is hydrogen or methyl.

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

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

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

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

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

13 . A 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 application to the locus of a weed controlling amount of a composition according to claim 1 .

15 . A method of controlling weeds by applying a compound of Formula (I) as defined in claim 1 .

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

• A01P13/00

  Herbicides; Algicides · CPC title

• C07D401/10

  linked by a carbon chain containing aromatic rings · CPC title

• C07D221/20 Primary

  Spiro-condensed ring systems · CPC title

• A01N43/42 Primary

  condensed with carbocyclic rings · CPC title

• C07D401/12

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