US 12,319,663 B2
Alkene-containing amide compound and application thereof
Bing Sun, Liaoning (CN); Huibin Yang, Liaoning (CN); Hongjuan Ma, Liaoning (CN); Junwu Ying, Liaoning (CN); Dongliang Cui, Liaoning (CN); Bo Qin, Liaoning (CN); Shuang Liang, Liaoning (CN); Gang Wang, Liaoning (CN); Zhengmao Lu, Liaoning (CN); Fan Zhang, Liaoning (CN); Lin Chen, Liaoning (CN); Heying Pei, Liaoning (CN); Yan Cheng, Liaoning (CN); Mingxin Wang, Liaoning (CN); and Bin Li, Liaoning (CN)
Assigned to SHENYANG SINOCHEM AGROCHEMICALS R&D CO., LTD., Liaoning (CN); and JIANGSU YANGNONG CHEMICAL CO., LTD., Jiangsu (CN)
Appl. No. 17/754,669
Filed by SHENYANG SINOCHEM AGROCHEMICALS R&D CO., LTD., Liaoning (CN); and JIANGSU YANGNONG CHEMICAL CO., LTD., Jiangsu (CN)
PCT Filed Sep. 30, 2020, PCT No. PCT/CN2020/119134
§ 371(c)(1), (2) Date Apr. 8, 2022,
PCT Pub. No. WO2021/068816, PCT Pub. Date Apr. 15, 2021.
Claims priority of application No. 201910950934.4 (CN), filed on Oct. 8, 2019; and application No. 202010174419.4 (CN), filed on Mar. 13, 2020.
Prior Publication US 2023/0037883 A1, Feb. 9, 2023
Int. Cl. C07D 257/06 (2006.01); A01N 43/713 (2006.01); A01N 43/80 (2006.01); A01N 43/82 (2006.01); A01P 13/00 (2006.01); C07D 249/14 (2006.01); C07D 271/04 (2006.01); C07D 271/113 (2006.01); C07D 285/135 (2006.01); C07D 401/12 (2006.01); C07D 401/14 (2006.01); C07D 403/12 (2006.01); C07D 405/12 (2006.01); C07D 413/12 (2006.01); C07D 413/14 (2006.01); C07D 417/12 (2006.01)
CPC C07D 257/06 (2013.01) [A01N 43/713 (2013.01); A01N 43/80 (2013.01); A01N 43/82 (2013.01); A01P 13/00 (2021.08); C07D 249/14 (2013.01); C07D 271/04 (2013.01); C07D 271/113 (2013.01); C07D 285/135 (2013.01); C07D 401/12 (2013.01); C07D 401/14 (2013.01); C07D 403/12 (2013.01); C07D 405/12 (2013.01); C07D 413/12 (2013.01); C07D 413/14 (2013.01); C07D 417/12 (2013.01)] 9 Claims
 
1. An alkene-containing amide compound of formula I, a stereoisomer of the compound, and/or an agriculturally acceptable salt thereof,

OG Complex Work Unit Chemistry
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;

OG Complex Work Unit Chemistry
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;

OG Complex Work Unit Chemistry
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.