1-(pyridazin-3-yl)-imidazolidin-2-one derivatives as herbicides
View Patent ↗The invention relates to pyrrolone compounds of the formula (I) wherein R 1 , R 2 , R 3 , R b , R c and R d 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.
1. A compound of formula (I)
wherein
X is selected from S and O;
R b is selected from hydrogen, halogen, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, C 1 -C 4 haloalkyl, C 1 -C 6 alkoxy, C 2 -C 4 alkenyloxy, C 2 -C 4 alkynyloxy, C 1 -C 4 alkoxy-C 1 -C 4 alkyl, C 1 -C 4 halolkoxy, C 1 -C 3 alkoxy-C 1 -C 3 alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, a group R 5 R 6 N—, a group R 5 C(O)N(R 6 )—, a group R 5 S(O 2 )N(R 6 )—, a group R 5 R 6 NSO 2 —, a group R 5 R 6 NC(O)—, aryl, aryloxy and heteroaryl, where aryl, aryloxy and heteroaryl are optionally substituted by one or more groups independently selected from halogen, nitro, cyano, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkyl and C 1 -C 3 haloalkoxy;
R c is selected from C 1 -C 6 haloalkyl or, when R b is R 5 R 6 NC(O)—, R c is selected from hydrogen, halogen, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl;
R d is selected from hydrogen, halogen, cyano, C 1 -C 6 alkyl and C 1 -C 6 haloalkyl;
or R c and R d 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, C 1 -C 6 alkyl and C 1 -C 6 haloalkyl;
R 1 is selected from hydrogen, hydroxyl, C 1 -C 6 alkyl optionally substituted with NR 10 R 11 , C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 4 cycloalkyl, C 1 -C 4 cyanoalkyl, C 1 -C 3 haloalkyl, C 1 -C 6 alkoxy and C 1 -C 4 alkoxy-C 1 -C 4 alkyl; wherein R 10 and R 11 are independently selected from hydrogen, C 1 -C 6 alkyl and C 1 -C 6 haloalkyl;
R 2 is selected from hydrogen, hydroxyl, halogen, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy, C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyloxy, C 1-C 6 haloalkyl, C 1 -C 6 haloalkoxy, C 1-C 6 alkoxy C 1 -C 6 alkyl, C 1 -C 4 alkoxy-C 1 -C 4 alkoxy, C 1 -C 4 hydroxyalkyl, C 1 -C 6 cyanoalkyl and the group —NR 12 R 13 , wherein R 12 and R 13 are independently selected from hydrogen and C 1 -C 6 alkyl;
or R 1 and R 2 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, C 1 -C 6 alkyl and C 1 -C 6 haloalkyl;
R 3 is selected from halogen, hydroxyl, —NR 14 R 15 or any one of the following groups
R 5 and R 6 are independently selected from hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 cyanoalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkoxy and C 1 -C 6 alkoxy-C 1 -C 6 alkyl or R 5 and R 6 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 C 1 -C 6 alkyl;
R 7 and R 8 are independently selected from
hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl,
a C 3 -C 6 cycloalkyl group optionally substituted with 1 to 3 groups independently selected from C 1 -C 3 alkyl, C 2 -C 4 alkenyl, C 1 -C 3 haloalkyl and C 2 -C 4 haloalkenyl,
a C 5 -C 10 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, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl and C 1 -C 3 alkoxy,
a C 5 -C 10 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, C 1 -C 3 alkyl, C 1 -C 3 haloalkyl and C 1 -C 3 alkoxy,
a C 6 -C 10 aryl group optionally substituted with 1 to 3 groups independently selected from halogen, nitro, cyano, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkyl and C 1 -C 3 haloalkoxy,
a C 6 -C 10 arylalkyl group optionally substituted with 1 to 3 groups independently selected from C 1 -C 4 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkyl and the group —OC(O)—C 1 -C 4 alkyl,
or R 7 and R 8 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 C 1 -C 6 alkyl;
R 9 is selected from C 1 -C 6 alkyl and benzyl optionally substituted with 1 to 3 groups independently selected from halogen, nitro, cyano, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkyl and C 1 -C 3 haloalkoxy;
R 14 and R 15 are, independently, selected from hydrogen, C 1 -C 20 alkyl, C 1 -C 20 haloalkyl, C 1 -C 20 alkoxy, C 1 -C 20 alkoxy-C 1 -C 20 alkyl, C 2 -C 20 alkenyl, C 2 -C 20 alkynyl and benzyl, or R 14 and R 15 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 C 1 -C 6 alkyl;
or an N-oxide or salt form thereof.
2. The compound of claim 1 , wherein X is O.
3. The compound of claim 1 , wherein R b is selected from hydrogen, halogen, methoxy, R 5 R 6 NC(O)—, heteroaryl substituted by halogen or methoxy groups and aryl substituted by halogen or methoxy groups.
4. The compound of claim 1 , wherein R c is selected from 1,1-difluoroethyl, difluoromethyl, 1-fluoro-1-methylethyl or trifluoromethyl, or, when R b is R 5 R 6 NC(O)—, R c is selected from hydrogen, Cl and trifluoromethyl.
5. The compound of claim 4 , wherein R c is selected from 1,1-difluoroethyl, 1-fluoro-1-methylethyl and trifluoromethyl.
6. The compound of claim 1 , wherein R d is hydrogen.
7. The compound of claim 1 , wherein R 1 is selected from C 1 -C 3 alkyl, C 1 -C 3 alkoxy and C 1 -C 3 haloalkyl.
8. The compound of claim 1 , wherein R 2 is selected from hydrogen, hydroxyl, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkyl and C 1 -C 3 alkoxy-C 1 -C 3 alkyl.
9. The compound of claim 1 , wherein R 3 is selected from halogen, hydroxyl, and any of the following groups
10. A herbicidal composition comprising a compound of formula I as defined in claim 1 together with an agriculturally acceptable adjuvant or diluent.
11. The composition of claim 10 further comprising an additional herbicide compound in addition to the compound of formula I.
12. The composition of claim 10 further comprising a safener.
13. A method of controlling weeds in crops of useful plants, comprising applying to said weeds or to a locus of said weeds, or to said useful plants or to a locus of said useful plants, a compound of formula I as defined in claim 1 .