Herbicidal compounds
The present invention relates to herbicidal heteroarylmethoxy/heterocyclylmethoxy substituted phenyl diones and heteroarylmethoxy/heterocyclylmethoxysubstituted phenyl-dioxo-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.
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 2 is CR 3a R 3b or NR 4 ;
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;
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 -C4alkyl-, 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 4 is hydrogen, C 1 -C 10 alkyl, C 1 -C 4 haloalkyl, C 2 -C 10 alkenyl, C 2 -C 4 haloalkenyl, 2 -C 10 alkynyl, C 2 -C 4 haloalkynyl, C 3 -C 10 cycloalkyl, C 3 -C 10 cycloalkyl-C 1 -C 6 alkyl-, C 1 -C 10 alkoxy-C 1 -C 6 alkyl-, C 1 -C 10 cyanoalkyl-, C 1 -C 10 alkoxycarbonyl-C 1 -C 6 alkyl-, N-C 1 -C 3 alkyl-aminocarbonyl-C 1 -C 6 alkyl-, N,N-di-(C 1 -C 3 alkyl)-aminocarbonyl-C 1 -C 6 alkyl-, aryl-C 1 -C 6 alkyl- or aryl-C 1 -C 6 alkyl- wherein the aryl moiety is substituted by one to three R 10 , which may be the same or different, or heterocyclyl-C 1 -C 6 alkyl- or heterocyclyl-C 1 -C 6 alkyl- wherein the heterocyclyl moiety is substituted by one to three R 10 , which may be the same or different;
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 - 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 haloalkyl, C 1 -C 3 alkoxy and C 1 -C 3 haloalkoxy; and
each R 10 is independently halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy;
Q is (i), (ii) or (iii)
wherein B designates the point of attachment to the rest of the molecule;
A 4 , A 5 , A 6 , A 7 , and A 8 , are independently CR 11 , NR 12 , N, S, O, or C(O), provided that at least one and no more than three of A 4 , A 5 , A 6 , A 7 , and A 8 is N, NR 12 , S, O, or C(O);
each R 11 is independently hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, halogen, cyano, hydroxyl, C 1 -C 4 alkoxy, or C 1 -C 4 alkylthio;
each R 12 is independently hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, hydroxyl, C 1 -C 4 alkoxy, or C 1 -C 4 alkylthio.
2. The compound of claim 1 wherein R 4 is hydrogen, C 1 -C 2 alkyl, C 1 -C 2 haloalkyl, C 2 -C 3 alkenyl or C 2 -C 3 alkynyl.
3. The compound of 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.
4. The compound according to claim 1 wherein Y is hydrogen, 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 Q-CH 2 O— moiety.
5. The compound according to claim 1 wherein A 3 is C(O).
6. The compound according to claim 1 wherein A 3 is S(O) 2 .
7. The compound according to claim 1 , wherein Q is an optionally substituted pyridyl, thiazolyl, oxazolyl, imidazolyl, isoxazolyl, isothiazolyl, pyrazolyl, pyrazinyl, pyridazinyl, pyrimidyl, or pyridone.
8. The compound according to claim 1 , wherein any two of A 4 , A 5 , A 6 , A 7 , and A 8 are independently N, NR 12 , S, O, or C(O) and all remaining A 4 , A 5 , A 6 , A 7 , and A 8 are CR 11 .
9. The compound according to claim 1 , wherein one of A 4 , A 5 , A 6 , A 7 , and A 8 is independently N and all remaining A 4 , A 5 , A 6 , A 7 , and A 8 are CR 11 .
10. The compound according to claim 1 wherein Q is (i) and is selected from the group consisting of:
11. The compound according to claim 1 wherein Q is (ii) and is selected from the group consisting of:
12. The compound according to claim 1 , wherein R 11 is independently hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, halogen, cyano, hydroxyl, C 1 -C 4 alkoxy, or C 1 -C 4 alkylthio.
13. The herbicidal composition comprising a herbicidal compound according to claim 1 and an agriculturally acceptable formulation adjuvant.
14. The herbicidal composition according to claim 13 , further comprising at least one additional pesticide.
15. 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.