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