Triazolotriazinone derivatives having activity a s herbicides
The present invention relates to compounds of Formula (I), or an agronomically acceptable salt of said compounds wherein Q, R 2 and R 3 are as defined herein. The invention further relates to herbicidal compositions which comprise a compound of Formula (I), to their use for controlling weeds, in particular in crops of useful plants, and to intermediates used to synthesize said compounds.
1. A compound of Formula (I):
or an agronomically acceptable salt thereof,
wherein:
Q is Q1 or Q2
A 1 and A 2 are independently selected from CH and N, wherein A 1 and A 2 are not both CH;
X 1 is selected from the group consisting of O, C(O) and (CR e R f );
R a , R b , R e , R d , R e and R f are each independently selected from the group consisting of hydrogen and C 1 -C 4 alkyl wherein R a and R c may together form a C 1 -C 3 alkylene chain;
R 1 is selected from the group consisting of C 1 -C 6 alkyl-, C 1 -C 6 haloalkyl-, C 1 -C 6 alkoxy-C 1 -C 3 alkyl-, C 1 -C 6 haloalkoxy-C 1 -C 3 alkyl- and phenyl wherein the phenyl is optionally substituted by one or more substituents selected from the group consisting of halogen, C 1 -C 6 alkyl-, C 1 -C 6 alkoxy-, nitro and cyano;
R 2 is selected from the group consisting of C 1 -C 6 alkyl-, C 1 -C 6 haloalkyl, C 2 -C 6 alkenyl-, C 2 -C 6 haloalkenyl-, C 2 -C 6 alkynyl-, C 2 -C 6 haloalkynyl-, C 1 -C 6 alkoxyC 1 -C 3 alkyl-, C 1 -C 6 haloalkoxyC 1 -C 3 alkyl-, C 1 -C 6 alkoxyC 2 -C 3 alkoxyC 1 -C 3 alkyl-, —(CH 2 ) n —C 3 -C 6 cycloalkyl, benzyl, phenyl and a five or six-membered heteroaryl, the heteroaryl containing from one to three heteroatoms each independently selected from the group consisting of oxygen, nitrogen and sulphur, and wherein the benzyl, phenyl or heteroaryl may be optionally substituted by one or more substituents selected from the group consisting of halogen, C 1 -C 6 alkyl-, C 2 -C 6 alkenyl-, C 2 -C 6 alkynyl-, C 1 -C 6 haloalkyl-, C 1 -C 6 alkoxy-, C 1 -C 6 alkoxyC 1 -C 3 alkyl-, C 1 -C 6 alkoxyC 1 -C 3 alkoxy-, C 1 -C 6 haloalkoxy-, C 1 -C 6 alkyl-S(O)p-, cyano and nitro;
R 3 is selected from the group consisting of hydrogen, C 1 -C 4 alkyl and C 1 -C 4 haloalkyl;
n=1, 2 or 3; and
p=0, 1 or 2.
2. A compound according to claim 1 , wherein Q is Q1 and A 1 and A 2 are both N.
3. A compound according to claim 1 , wherein R 1 is selected from the group consisting of methyl, ethyl and n-propyl.
4. A compound according to claim 1 , wherein Q is Q2, X 1 is CR e R f and R a , R b , R c , R d , R e and R f are hydrogen.
5. A compound according to claim 1 , wherein R 2 is selected from the group consisting of C 1 -C 6 alkyl- and C 1 -C 6 haloalkyl-.
6. A compound according to claim 1 , wherein R 2 is phenyl which is optionally substituted by one or more substituents selected from the group consisting of halogen, C 1 -C 6 alkyl-, C 1 -C 6 alkoxy- and C 1 -C 6 alkyl-S(O)p-.
7. A compound according to claim 1 , wherein R 3 is hydrogen.
8. A compound according to claim 2 , wherein R 1 is selected from the group consisting of methyl, ethyl and n-propyl.
9. A compound according to claim 8 , wherein R 3 is hydrogen.
10. A compound according to claim 9 , wherein R 2 is phenyl which is optionally substituted by one or more substituents selected from the group consisting of halogen, C 1 -C 6 alkyl-, C 1 -C 6 haloalkyl-, C 1 -C 6 alkoxy- and C 1 -C 6 alkyl-S(O)p-.
11. A compound according to claim 9 , wherein R 2 is selected from the group consisting of C 1 -C 6 alkyl- and C 1 -C 6 haloalkyl-.
12. A herbicidal composition comprising a compound according to claim 1 and an agriculturally acceptable formulation adjuvant.
13. A herbicidal composition according to claim 12 , further comprising at least one additional pesticide.
14. A herbicidal composition according to claim 13 , wherein the additional pesticide is a herbicide or herbicide safener.
15. A method of controlling weeds at a locus comprising application to the locus of a weed controlling amount of a composition according to claim 12 .