IP Library Granted Patent US 12672655
Granted Patent B2
US 12672655 · App. 17/754,670 · Granted Jul 7, 2026

Alkene-containing carboxylate compound and use thereof

Inventors: Bing Sun (Shenyang, CN); Huibin Yang (Shenyang, CN); Hongjuan Ma (Shenyang, CN); Junwu Ying (Shenyang, CN); Dongliang Cui (Shenyang, CN); Bo Qin (Shenyang, CN); Shuang Liang (Shenyang, CN); Gang Wang (Shenyang, CN); Lu Shang (Shenyang, CN); Fan Zhang (Shenyang, CN); Lin Chen (Shenyang, CN); Heying Pei (Shenyang, CN); Zheng Wang (Shenyang, CN); Mingxin Wang (Shenyang, CN); Bin Li (Shenyang, CN)
Assignees: SHENYANG SINOCHEM AGROCHEMICALS R&D CO., LTD; JIANGSU YANGNONG CHEMICAL CO., LTD.
A01N43/56A01N43/80A01N47/06A01N47/12A01N47/30A01P13/00C07D231/20C07D231/24C07D401/06C07D401/10C07D401/12C07D403/10C07D405/12C07D405/14C07D413/10C07D413/14
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Quick Facts
Patent No.
US 12672655
App. No.
17/754,670
Granted
Jul 7, 2026
Kind
B2
Abstract

An alkene-containing carboxylic ester compound of formula (I) and its agriculturally acceptable salt can be used as a herbicide.

Claims (40)

1 . An alkene-containing carboxylic ester compound of formula 1, a stereoisomer thereof, or an agriculturally acceptable salt thereof,

wherein:

X 1 is selected from halogen, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkyl, and C 1 -C 6 haloalkyl;

W is selected from CX 2 ;

X 2 is selected from Y 1 oxy, Y 1 sulfonyl, Y 1 oxy C 1 -C 6 alkyl, Y 1 sulfonyl C 1 -C 6 alkyl, 5-7 membered alicyclic heterocycle containing 1-4 heteroatoms, 5-7 membered aromatic heterocycle containing 1-4 heteroatoms, 5-7 membered aliphatic heterocyclic C 1 -C 6 alkyl containing 1-4 heteroatoms, and 5-7 membered aromatic heterocyclic C 1 -C 6 alkyl containing 1-4 heteroatoms; wherein at least one hydrogen on the aliphatic heterocycle or the aromatic heterocycle is optionally substituted by a substituent selected from nitro, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkoxy, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, phenyl, and halophenyl;

Y 1 is selected from C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl C 1 -C 6 alkyl, C 1 -C 6 alkoxy C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, phenyl, 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms, 5-7 membered aromatic heterocycle containing 1-4 heteroatoms, 5-7 membered aliphatic heterocyclic C 1 -C 6 alkyl containing 1-4 heteroatoms, and 5-7 membered aromatic heterocyclic C 1 -C 6 alkyl containing 1-4 heteroatoms; wherein at least one hydrogen on the phenyl, the aliphatic heterocycle, or the aromatic heterocycle is substituted by a substituent selected from nitro, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkoxy, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, phenyl, and halophenyl;

X 3 is selected from halogen, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkyl, and C 1 -C 6 haloalkyl;

wherein,

when X 1 is chlorine and X 3 is methylsulfonyl, X 2 is not 2-thiazolyl;

Z 1 is selected from C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 1 -C 6 alkylsulfonyl C 1 -C 6 alkyl, and phenyl;

Z 2 is selected from H, C 1 -C 6 alkyl, C 4 -C 6 cycloalkyl, C 1 -C 6 haloalkyl, and phenyl, wherein at least one hydrogen on the phenyl ring is optionally substituted by a substitute selected from halogen, cyano, nitro, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, and C 1 -C 6 haloalkyl; and

Q is Q 2 , and Q 2 is a C 3 -C 8 cycloalkenyl in which at least one hydrogen on the ring thereof is optionally substituted by a substituent selected from nitro, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 alkenyl, and C 3 -C 6 cycloalkyl.

2 . The compound according to claim 1 , wherein, in formula I:

X 1 is selected from halogen and C 1 -C 6 alkyl;

W is selected from CX 2 ;

X 2 is selected from Y 1 oxy;

Y 1 is selected from C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl C 1 -C 6 alkyl, C 1 -C 6 alkoxy C 1 -C 6 alkyl, phenyl, a 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms, a 5-7 membered aromatic heterocycle containing 1-4 heteroatoms, a 5-7 membered aliphatic heterocyclic C 1 -C 6 alkyl containing 1-4 heteroatoms, and a 5-7 membered aromatic heterocyclic C 1 -C 6 alkyl containing 1-4 heteroatoms; wherein at least one hydrogen on the phenyl; the aliphatic heterocycle, or the aromatic heterocycle is substituted by one or more substituents selected from nitro, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 6 cycloalkyl, and C 3 -C 6 cycloalkoxy;

X 3 is selected from C 1 -C 6 alkylsulfonyl;

Z 1 is selected from C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl C 1 -C 6 alkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, and phenyl; and

Z 2 is selected from H, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, and phenyl, wherein at least one hydrogen on the phenyl ring is optionally substituted by a substituent selected from halogen, cyano, nitro, C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, and C 1 -C 6 haloalkyl.

3 . The compound according to claim 2 , wherein, in formula I:

X 1 is selected from halogen or C 1 -C 3 alkyl;

W is selected from CX 2 ;

X 2 is selected from Y 1 oxy;

Y 1 is selected from C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl C 1 -C 6 alkyl, C 1 -C 6 alkoxy C 1 -C 6 alkyl, a 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms, a 5-7 membered aromatic heterocycle containing 1-4 heteroatoms, a 5-7 membered aliphatic heterocyclic C 1 -C 6 alkyl containing 1-4 heteroatoms, and a 5-7 membered aromatic heterocyclic C 1 -C 6 alkyl containing 1-4 heteroatoms; wherein at least one hydrogen on the aliphatic heterocycle or the aromatic heterocycle is substituted by one or more substituents selected from nitro, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 6 cycloalkyl, and C 3 -C 6 cycloalkoxy;

X 3 is selected from C 1 -C 3 alkylsulfonyl;

Z 1 is selected from C 1 -C 6 alkyl and C 3 -C 6 cycloalkyl;

Z 2 is selected from H and C 1 -C 6 alkyl; and

Q 2 is a C 3 -C 8 cycloalkenyl in which at least one hydrogen on the ring thereof is optionally substituted by a substutuent selected from C 1 -C 6 alkyl, C 1 -C 6 alkoxy, and C 1 -C 6 alkenyl.

4 . The compound according to claim 3 , wherein, in formula I:

X 1 is selected from halogen or C 1 -C 3 alkyl;

W is selected from CX 2 ;

X 2 is selected from Y 1 oxy;

Y 1 is selected from C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl C 1 -C 6 alkyl, C 1 -C 6 alkoxy C 1 -C 6 alkyl, a 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms, a 5-7 membered aromatic heterocycle containing 1-4 heteroatoms, a 5-7 membered aliphatic heterocyclic C 1 -C 6 alkyl containing 1-4 heteroatoms, and a 5-7 membered aromatic heterocyclic C 1 -C 6 alkyl containing 1-4 heteroatoms, wherein at least one hydrogen on the aliphatic heterocycle or the aromatic heterocycle is optionally substituted by a substituent selected from nitro, halogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 3 -C 6 cycloalkyl, and C 3 -C 6 cycloalkoxy;

X 3 is selected from C 1 -C 3 alkylsulfonyl;

Z 1 is selected from C 1 -C 3 alkyl;

Z 2 is selected from H and C 1 -C 3 alkyl; and

Q 2 is selected from G1, G2, G3, G4, G5, and G6 group:

5 . A herbicidal composition, comprising an active ingredient and an agriculturally acceptable carrier, wherein the active ingredient is the compound of formula I, a stereoisomer thereof, or an agriculturally acceptable salt thereof according to claim 1 ; and the weight percentage of the active ingredient in the composition is 1-99%.

6 . A method for controlling weeds comprising applying a herbicidally effective dose of the herbicidal composition of claim 5 to a weed or a growth medium or site of the weed.