Dihydro-hydantoin derivatives with herbicidal activity

A compound of formula (I)

• wherein
• X is selected from S and O;
• Ra is selected from hydrogen, C1-C6 alkyl and C1-C6 haloalkyl;
• Rb is selected from hydrogen, formyl, hydroxyl, halogen, nitro, cyano, C1-C6 alkyl, C1-C6 cyanoalkyl, C3-C6 cycloalkyl, C3-C6 cyanocycloalkyl, C1-C6 haloalkyl, C1-C6 alkylthio, C1-C6 alkoxy, C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkylthio C1-C6 alkyl, C1-C6 cyanoalkoxy, C1-C6 haloalkoxy, C1-C6 alkoxy C1-C6 alkoxy, C2-C6 alkenyl, C2-C6 alkynyl, C2-C6 cyanoalkenyl, C2-C6 cyanoalkynyl, C2-C6 alkenyloxy, C2-C6 alkynyloxy, C2-C6 haloalkenyl, C2-C6 haloalkynyl, C2-C6 haloalkenyloxy, C2-C6 haloalkynyloxy, C1-C6 alkoxy C2-C6 alkenyl, C1-C6 alkoxy C2-C6 alkynyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, C1-C6 haloalkylthio, C1-C6 haloalkylsulfinyl, C1-C6 haloalkylsulfonyl, C1-C6 alkylsulfonyloxy, C1-C6 alkylcarbonyl, C1-C6 haloalkylcarbonyl, C2-C6 alkenylcarbonyl, C2-C6 alkynylcarbonyl, C2-C6 haloalkenylcarbonyl, C2-C6 haloalkynylcarbonyl, tri C1-C6 alkylsilyl C2-C6 alkynyl, a group R5R6N—, a group R5C(O)N(R6)—, a group R5R6NC(O)—, a group R5S(O2)N(R6)—, a group R5R6NSO2—, a C6-C10 aryl group optionally substituted by from 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 aryloxy group optionally substituted by from 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 benzyl group optionally substituted by from 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 benzyloxy group optionally substituted by from 1 to 3 groups independently selected from halogen, nitro, cyano, C1-C3 alkyl, C1-C3 alkoxy, C1-C3 haloalkyl and C1-C3 haloalkoxy, a C3-C6 heterocyclyl group optionally substituted by from 1 to 3 groups independently selected from C1-C4 alkyl and a C3-C6 cycloalkyl group optionally substituted with from 1 to 3 groups independently selected from halogen or C1-C6 alkyl;
• Rc is selected from hydrogen, halogen, cyano, C1-C6 alkyl and C1-C6 haloalkyl;
• or Ra and Rb 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 halogen, C1-C6 alkyl and C1-C6 haloalkyl;
• or Rb and Rc together with the 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 halogen, C1-C6 alkyl and C1-C6 haloalkyl;
• R1 is selected from hydrogen, C1-C4 alkyl, C1-C4 alkoxy and C1-C4 haloalkyl;
• R2 is selected from hydrogen, hydroxyl, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkoxy-C1-C4 alkyl, C1-C4 haloalkyl, C1-C3 haloalkoxy and C1-C4 cyanoalkyl;
• 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 or C1-C6 haloalkyl;
• R3 is selected from halogen, hydroxyl, —NR10R11 and any one of the following groups
• R5 and R6 are independently selected from hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl and C2-C6 alkynyl;
• R7 and R8 are independently selected from hydrogen, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, 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 and a C6-C10 aryl group optionally substituted with 1 to 3 groups independently selected from halogen, nitro, cyano, C1-C3 alkyl, C1-C3 or R7 and R8 together with the atoms to alkoxy, C1-C3 haloalkyl and C1-C3 haloalkoxy, 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 or 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;
• and
• R10 and R11 are, independently, selected from hydrogen, C1-C20 alkyl, C1-C20 haloalkyl, C2-C20 alkenyl and C2-C20 alkynyl.