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US 12,319,663 B2Granted
Alkene-containing amide compound and application thereof
AssigneesShenyang Sinochem Agrochemicals R&D Co., Ltd., Jiangsu Yangnong Chemical Co., Ltd.
InventorsBing Sun, Huibin Yang, Hongjuan Ma, Junwu Ying, Dongliang Cui, Bo Qin, Shuang Liang, Gang Wang, Zhengmao Lu, Fan Zhang, Lin Chen, Heying Pei, Yan Cheng, Mingxin Wang, Bin Li
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Abstract
An alkene-containing amide compound of formula (I) and agriculturally acceptable salts thereof can be used as herbicides.
Claims9
An alkene-containing amide compound of formula I, a stereoisomer of the compound, and/or an agriculturally acceptable salt thereof,
- wherein:
- X1 and X3 are independently selected from halogen, C1-C6 alkylsulfonyl, C1-C6 alkyl, and C1-C6 haloalkyl;
- W is CX2, X2 being hydrogen, Y1 oxy, Y1 oxy C1-C6 alkyl, Y1 sulfonyl C1-C6 alkyl, 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms, 5-7 membered aromatic heterocycle containing 1-4 heteroatoms, 5-7 membered aliphatic heterocyclic C1-C6 alkyl containing 1-4 heteroatoms, or 5-7 membered aromatic heterocyclic C1-C6 alkyl containing 1-4 heteroatoms,
- wherein hydrogen on 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms or the 5-7 membered aromatic heterocycle containing 1-4 heteroatoms is unsubstituted or substituted by one or more substituents selected from nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 cycloalkyl, C3-C6 cycloalkoxy, C2-C6 alkenyl, C2-C6 alkynyl, phenyl, and halophenyl;
- Y1 is selected from C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C1-C6 alkoxy C1-C6 alkyl, phenyl, 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms, 5-7 membered aromatic heterocycle containing 1-4 heteroatoms, 5-7 membered aliphatic heterocyclic C1-C6 alkyl containing 1-4 heteroatoms, and 5-7 membered aromatic heterocyclic C1-C6 alkyl containing 1-4 heteroatoms, wherein hydrogen on the phenyl, the 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms, and the 5-7 membered the aromatic heterocycle containing 1-4 heteroatoms is unsubstituted or substituted by one or more substituents selected from nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 cycloalkyl, C3-C6 cycloalkoxy, C2-C6 alkenyl, C2-C6 alkynyl, phenyl, and halophenyl;
- Z is Z1 or Z2;
- Z2 is C3-C8 cycloalkenyl that is unsubstituted or having hydrogen on the ring thereof substituted by one or more substituents selected from nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkenyl, and C3-C6 cycloalkyl;
- Q is Q2, or Q6 group;
- B represents the carbon-carbon double bond, and the stereoisomer of the compound is a cis-stereoisomer in which hydrogen atoms are on a same side of the carbon-carbon double bond B or a trans-stereoisomer in which hydrogen atoms are on both sides of the carbon-carbon double bond B;
- R1 to R5 are independently selected from hydrogen, hydroxyl, cyano, nitro, halogen, phenyl, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, and benzyloxy, wherein
- R1 and R2 form a benzene ring, a 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms or a 5-7 membered aromatic heterocycle containing 1-4 heteroatoms together with the carbon atoms on the connected benzene ring;
- R2 and R3 form a benzene ring, a 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms or a 5-7 membered aromatic heterocycle containing 1-4 heteroatoms together with the carbon atoms on the connected benzene ring;
- R7 is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or phenyl;
- and
- R11 is selected from hydrogen, halogen, cyano, nitro, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C3 alkoxy C1-C3 alkyl, C1-C6 alkoxy C1-C3 alkoxy, C1-C6 alkoxy C1-C3 alkoxy C1-C3 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkyl C1-C3 alkoxy, and C3-C6 cycloalkyloxy.
12 more elements
An alkene-containing amide compound of formula I, a stereoisomer of the compound, and/or an agriculturally acceptable salt thereof,
- wherein:
- X1 and X3 are independently selected from halogen, C1-C6 alkylsulfonyl, C1-C6 alkyl, and C1-C6 haloalkyl;
- W is CX2, X2 being hydrogen, Y1 oxy, Y1 oxy C1-C6 alkyl, Y1 sulfonyl C1-C6 alkyl, 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms, 5-7 membered aromatic heterocycle containing 1-4 heteroatoms, 5-7 membered aliphatic heterocyclic C1-C6 alkyl containing 1-4 heteroatoms, or 5-7 membered aromatic heterocyclic C1-C6 alkyl containing 1-4 heteroatoms,
- wherein hydrogen on 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms or the 5-7 membered aromatic heterocycle containing 1-4 heteroatoms is unsubstituted or substituted by one or more substituents selected from nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 cycloalkyl, C3-C6 cycloalkoxy, C2-C6 alkenyl, C2-C6 alkynyl, phenyl, and halophenyl;
- Y1 is selected from C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C1-C6 alkoxy C1-C6 alkyl, phenyl, 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms, 5-7 membered aromatic heterocycle containing 1-4 heteroatoms, 5-7 membered aliphatic heterocyclic C1-C6 alkyl containing 1-4 heteroatoms, and 5-7 membered aromatic heterocyclic C1-C6 alkyl containing 1-4 heteroatoms, wherein hydrogen on the phenyl, the 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms, and the 5-7 membered the aromatic heterocycle containing 1-4 heteroatoms is unsubstituted or substituted by one or more substituents selected from nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C3-C6 cycloalkyl, C3-C6 cycloalkoxy, C2-C6 alkenyl, C2-C6 alkynyl, phenyl, and halophenyl;
- Z is Z2, and Z2 is C3-C8 cycloalkenyl that is unsubstituted or having hydrogen on the ring thereof substituted by one or more substituents selected from nitro, halogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkenyl, and C3-C6 cycloalkyl;
- Q is Q1 group:
- B represents the carbon-carbon double bond, and the stereoisomer of the compound is a cis-stereoisomer in which hydrogen atoms are on a same side of the carbon-carbon double bond B or a trans-stereoisomer in which hydrogen atoms are on both sides of the carbon-carbon double bond B;
- R1 to R5 are independently selected from hydrogen, hydroxyl, cyano, nitro, halogen, phenyl, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C6 alkylthio, and benzyloxy, wherein
- R1 and R2 form a benzene ring, a 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms or a 5-7 membered aromatic heterocycle containing 1-4 heteroatoms together with the carbon atoms on the connected benzene ring;
- R2 and R3 form a benzene ring, a 5-7 membered aliphatic heterocycle containing 1-4 heteroatoms or a 5-7 membered aromatic heterocycle containing 1-4 heteroatoms together with the carbon atoms on the connected benzene ring;
- R7 is hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, or phenyl;
- and
- R11 is selected from hydrogen, halogen, cyano, nitro, C1-C6 alkylsulfonyl, C1-C6 haloalkylsulfonyl, C1-C6 alkylsulfinyl, C1-C6 haloalkylsulfinyl, C1-C6 alkylthio, C1-C6 haloalkylthio, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, C1-C6 haloalkoxy, C1-C3 alkoxy C1-C3 alkyl, C1-C6 alkoxy C1-C3 alkoxy, C1-C6 alkoxy C1-C3 alkoxy C1-C3 alkyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkyl C1-C3 alkoxy, and C3-C6 cycloalkyloxy.
11 more elements
Dependencies are inferred from the claim text.