Herbicidal Compounds
AssigneeSyngenta Participations AG
InventorsJames Alan MORRIS, Mangala PHADATE, Ravindra SONAWANE, Claire Janet RUSSELL, Donn Warwick MOSELEY, Adrian LONGSTAFF, Matthew Brian HOTSON, Alan Joseph HENNESSY
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Abstract
The invention relates to substituted pyrrolone derivatives of the formula (I) wherein X, A, R1, R2 and R3 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 or inhibit plant growth.
Claims23
A compound of formula (I)
- wherein
- X is selected from S and O;
- A is:
- Rb is selected from C1-C6 alkyl substituted with one or more groups independently selected from hydroxyl, halogen, cyano and C1-C6 alkoxy and, when R1 or R2 is C2-C6 alkynyl or one of R1 or R2 is C2 or C3 alkyl and the other is not H, or R1 and R2 together form a ring structure as described below, Rb can also be C1-C6 alkyl;
- Rc is selected from hydrogen, halogen, cyano, C1-C6 alkyl and C1-C6 haloalkyl;
- R1 is selected from hydrogen, C1-C6 alkyl optionally substituted with NR10R11, C1-C3 haloalkyl, C1-C6 alkoxy and C2-C6 alkynyl;
- wherein R10 and R11 are independently selected from hydrogen, C1-C6 alkyl and C1-C6 haloalkyl.
- R2 is selected from hydrogen, hydroxyl, halogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 haloalkyl, C1-C6 haloalkoxy, C1-C6 alkoxy C1-C6 alkyl, and the group —NR12R13, wherein R12 and R13 are independently selected from hydrogen and C1-C6 alkyl.
- 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, —NR5R6, or any one of the following groups
- R5 and R6 are, independently, selected from hydrogen, C1-C20 alkyl, C1-C20 haloalkyl, C2-C20 alkenyl and C2-C20 alkynyl, 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 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, or R7 and R9 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 or 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;
- or an N-oxide or salt form thereof
- with the provisos that
- (i) when R1 is methyl, A is
- Rb is C1-C6 cyanoalkyl or C1-C6 haloalkyl then R2 is not C1-C4 alkoxy or C1-C4 alkoxy-C1-C4-alkyl;
- (ii) when R1 is C1-C3 alkyl, R2 is hydrogen, hydroxyl, methyl or allyl, Rb is not C1-C6 alkyl substituted by halogen or C1-C6 alkoxy;
- (iii) when R1 is C1-C3 alkyl, R2 is H, A is
- then Rb is not C1-C6 alkyl substituted by halogen.
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Dependencies are inferred from the claim text.