Herbicidal Compounds

摘要

The invention relates to pyrrolone compounds of the formula (I), wherein X, R1, R2, R3, Ra, Rb, Rc and Rd are as defined in the specification. Furthermore, the present invention relates to processes and intermediates for making compounds of formula (I), to herbicidal compositions comprising these compounds and to methods of using these compounds to control plant growth.;

主权项

1. A herbicidal compound of formula (I) wherein X is selected from S and O; Ra is selected from hydrogen and halogen; Rb is selected from hydrogen, halogen, C1-C4 alkyl, C2-C4 alkenyl C1-C4 haloalkyl, C1-C6 alkoxy, C2-C4 alkenyloxy, C2-C4 alkynyloxy, C1-C4 alkoxy-C1-C4 alkyl, C1-C4 haloalkoxy, C1-C3 alkoxy-C1-C3 alkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, a group R5R6N—, a group R5C(O)N(R6)—, a group R5S(O2)N(R6)—, a group R5R6NSO2—, a group R5R6NC(O)—, aryl optionally substituted by one or more groups independently selected from halogen, nitro, cyano, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl and C1-C3 haloalkoxy, aryloxy optionally substituted by one or more groups independently selected from halogen, nitro, cyano, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl and C1-C3 haloalkoxy and heteroaryl optionally substituted by one or more groups independently selected from halogen, nitro, cyano, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl and C1-C3 haloalkoxy; Rc is selected from hydrogen, halogen, C1-C8 alkyl, C1-C6 haloalkyl, C2-C8 alkenyl, C1-C6 cyanoalkyl, C1-C6 alkoxy, C1-C4 alkoxy-C1-C4 alkyl, C1-C6 hydroxyalkyl, C2-C6 alkenyloxy C1-C6 alkyl and C3-C6 cycloalkyl optionally substituted by from 1 to 3 groups independently selected from cyano, C1-C3 alkyl and C1-C3 alkoxy; Rd is selected from hydrogen, halogen, cyano, C1-C6 alkyl and C1-C6 haloalkyl; R1 is selected from hydrogen, hydroxyl, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 cyanoalkyl, C3-C6 cycloalkyl, C1-C4 alkoxy, C1-C4 alkoxy-C1-C4 alkyl and C1-C4 haloalkyl and R2 is selected from hydrogen, hydroxyl, C1-C4 alkyl, C2-C4 alkenyl, C1-C4 alkoxy, C2-C4 alkenyloxy, C2-C4 alkynyloxy, C1-C4 alkoxy-C1-C4 alkyl, C1-C4 alkoxy-C1-C4 alkoxy, C1-C4 hydroxyalkyl, C1-C4 haloalkyl, C1-C3 haloalkoxy and C1-C4 cyanoalkyl, with the proviso that when R1 is methyl, R2 is not H; or R1 and R2 together with the nitrogen and carbon atoms to which they are attached form a 3-7 membered saturated or partially unsaturated ring optionally comprising from 1 to 3 heteroatoms independently selected from S, O and N and optionally substituted with from 1 to 3 groups independently selected from hydroxyl, ═O, C1-C6 alkyl and C1-C6 haloalkyl. R3 is selected from halogen, hydroxyl, —NR14R15, or any one of the following groups R5 and R6 are independently selected from hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 cyanoalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy and C1-C6 alkoxy-C1-C6 alkyl, or R5 and R6 together with the carbon atoms to which they are attached form a 3-6 membered saturated or partially unsaturated ring optionally comprising from 1 to 3 heteroatoms independently selected from S, O and N and optionally substituted with from 1 to 3 groups independently selected from halogen and C1-C6 alkyl; R7 and R8 are independently selected from hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, a C3-C6 cycloalkyl group optionally substituted with 1 to 3 groups independently selected from C1-C3 alkyl, C2-C4 alkenyl, C1-C3 haloalkyl and C2-C4 haloalkenyl, a C5-C10 heterocyclyl group which can be mono- or bicyclic comprising from 1 to 4 heteroatoms independently selected from N, O and S and optionally substituted with 1 to 3 groups independently selected from halogen, C1-C3 alkyl, C1-C3 haloalkyl and C1-C3 alkoxy, a C5-C10 heteroaryl group which can be mono- or bicyclic comprising from 1 to 4 heteroatoms independently selected from N, O and S and optionally substituted with 1 to 3 groups independently selected from halogen, C1-C3 alkyl, C1-C3 haloalkyl and C1-C3 alkoxy, a C6-C10 aryl group optionally substituted with 1 to 3 groups independently selected from halogen, nitro, cyano, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl and C1-C3 haloalkoxy, a C6-C10 arylalkyl group optionally substituted with 1 to 3 groups independently selected from C1-C4 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl and the group —OC(O)—C1-C4 alkyl, or R7 and R8 together with the atoms to which they are attached form a 3-6 membered saturated or partially unsaturated ring optionally comprising from 1 to 3 heteroatoms independently selected from S, O and N and optionally substituted with from 1 to 3 groups independently selected from halogen and C1-C6 alkyl; R9 is selected from C1-C6 alkyl and benzyl optionally substituted with 1 to 3 groups independently selected from halogen, nitro, cyano, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl and C1-C3 haloalkoxy; R14 and R15 are independently selected from hydrogen, C1-C20 alkyl, C1-C20 haloalkyl, C1-C20 alkoxy, C1-C20 alkoxy-C1-C20 alkyl, C2-C20 alkenyl, C2-C20 alkynyl and benzyl, or R14 and R15 together with the carbon atoms to which they are attached form a 3-6 membered saturated or partially unsaturated ring optionally comprising from 1 to 3 heteroatoms independently selected from S, O and N and optionally substituted with from 1 to 3 groups independently selected from halogen and C1-C6 alkyl; or an N-oxide or salt form thereof.