Herbicidal compounds
The present invention relates to herbicidal benzyloxy-substituted phenyl diones and benzyloxy-substituted phenyl-di-oxo-thiazinone derivatives of formula (I), as well as to processes and intermediates used for the preparation of such derivatives. The invention further extends to herbicidal compositions comprising such derivatives, as well as to the use of such compounds and compositions in controlling undesirable plant growth: in particular the use in controlling weeds, such as broad-leaved dicotyledonous weeds, in crops of useful plants, or a salt or N-oxide thereof;
1. A compound of formula (I)
or a salt or N-oxide thereof;
wherein A 1 is CR 1 or N;
R 1 is hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, halogen, cyano, or hydroxyl;
A 3 is C(O) or S(O) 2 ;
G is hydrogen, or C(O)R 6 ;
X and Y are each independently hydrogen, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkyl, C 1 -C 3 haloalkoxy, or halogen;
n is an integer of 0, 1, 2, 3, 4, or 5;
each Z is independently C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkyl, C 1 -C 3 haloalkoxy, or halogen;
R 3a and R 3b are independently hydrogen, halogen, cyano, C 1 -C 8 alkyl, C 1 -C 8 alkoxy-C 1 -C 4 alkyl-, C 1 -C 8 haloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl, C 3 -C 10 ocycloalkyl, C 3 -C 10 cycloalkyl-C 1 -C 4 alkyl-, heterocyclyl, heterocyclyl-C 1 -C 4 alkyl-, or C 1 -C 8 alkoxycarbonyl-; or R 3a and R 3b together with the carbon atom they are attached to join to form a 3- to 10-membered carbocyclic ring or a 4- to 10-membered heterocyclic ring;
R 6 is selected from the group consisting of C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkyl-S—, —NR 7 R 8 and phenyl optionally substituted by one or more R 9 ;
R 7 and R 8 are independently selected from the group consisting of C 1 -C 6 alkyl and C 1 -C 6 alkoxy, or R 7 and R 8 together can form a morpholinyl ring; and,
R 9 is selected from the group consisting of halogen, cyano, nitro, C 1 -C 3 alkyl, C 1 -C 3 haloalky, C 1 -C 3 alkoxy and C 1 -C 3 haloalkoxy; and
with the proviso that when A 1 is CR 1 , A 3 is C(O).
2. The compound of claim 1 , wherein G is hydrogen, or C(O)R 6 wherein R 6 is isopropyl, tert-butyl, methyl, ethyl, propargyl or methoxy.
3. The compound of claim 1 , wherein R 3a and R 3b are each independently hydrogen, halogen, C 1 -C 8 alkyl, C 1 -C 8 haloalkyl or C 2 -C 8 alkynyl.
4. The compound according to claim 1 wherein X is C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkyl, C 1 -C 3 haloalkoxy, or halogen, and is ortho with respect to the bi-cyclic moiety.
5. The compound according to claim 1 wherein Y is C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkyl, C 1 -C 3 haloalkoxy, or halogen, and is ortho with respect to the benzyloxy moiety.
6. The compound according to claim 1 wherein A 3 is C(O).
7. The compound according to claim 1 wherein A 3 is S(O) 2 .
8. The compound according to claim 1 wherein R 1 is selected from the group consisting of hydrogen, halogen, C 1 -C 3 alkyl and C 1 -C 3 alkoxy.
9. The compound according to claim 1 wherein n is 0, 1 or 2.
10. The compound according to claim 1 wherein each Z is independently selected from halogen, methyl, methoxy, trifluoromethyl, and trifluoromethoxy.
11. The compound according to claim 1 , wherein A 1 is CR 1 .
12. The compound according to claim 1 , X and Y are each independently C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkyl, C 1 -C 3 haloalkoxy, or halogen.
13. The compound according to claim 12 , wherein X and Y are ortho with respect to each other.
14. The compound according to claim 1 , wherein X and Y are each independently C 1 -C 3 haloalkyl or halogen.
15. A herbicidal composition comprising a herbicidal compound according to claim 1 and an agriculturally acceptable formulation adjuvant.
16. A herbicidal composition according to claim 15 , further comprising at least one additional pesticide.
17. A method of controlling unwanted plant growth, comprising applying a compound of formula (I) as defined in claim 1 , to the unwanted plants or to the locus thereof.
18. A compound of formula (I)
or a salt, tautomer, or N-oxide thereof;
wherein A 1 is CR 1 or N;
R 1 is hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, halogen, cyano, or hydroxyl;
A 3 is C(O) or S(O) 2 ;
G is hydrogen, or C(O)R 6 ;
X and Y are each independently hydrogen, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkyl, C 1 -C 3 haloalkoxy, or halogen;
n is an integer of 0, 1, 2, 3, 4, or 5;
each Z is independently C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 haloalkyl, C 1 -C 3 haloalkoxy, or halogen;
R 3a and R 3b are independently hydrogen, halogen, cyano, C 1 -C 8 alkyl, C 1 -C 8 alkoxy-C 1 -C 4 alkyl-, C 1 -C 8 haloalkyl, C 2 -C 8 alkenyl, C 2 -C 8 haloalkenyl, C 2 -C 8 alkynyl, C 2 -C 8 haloalkynyl, C 3 -C 10 cycloalkyl, C 3 -C 10 cycloalkyl-C 1 -C 4 alkyl-, heterocyclyl, heterocyclyl-C 1 -C 4 alkyl-, or C 1 -C 8 alkoxycarbonyl-; or R 3a and R 3b together with the carbon atom they are attached to join to form a 3-to 10-membered carbocyclic ring or a 4-to 10-membered heterocyclic ring;
R 6 is selected from the group consisting of C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 1 -C 6 alkyl-S-, -NR 7 R 8 and phenyl optionally substituted by one or more R 9 ;
R 7 and R 8 are independently selected from the group consisting of C 1 -C 6 alkyl and C 1 -C 6 alkoxy, or R 7 and R 8 together can form a morpholinyl ring; and,
R 9 is selected from the group consisting of halogen, cyano, nitro, C 1 -C 3 alkyl, C 1 -C 3 haloalky, C 1 -C 3 alkoxy and C 1 -C 3 haloalkoxy; and
with the proviso that when A 1 is CR 1 , A 3 is C(O).
19. The compound according to claim 18 , wherein the compound is selected from the group consisting of: