Herbicidal pyridazinone compounds
The present invention relates to compounds of Formula (I), or an agronomically acceptable salt of said compounds wherein R 1a , R 1b , R 2 , X, A, R a , R b , R c , R d and m are as defined herein. The invention further relates to herbicidal compositions which comprise a compound of Formula (I), to their use for controlling weeds. The invention further relates to intermediate compounds used to produce compounds of Formula (I).
1. A compound of Formula (I):
or an agronomically acceptable salt thereof,
wherein:
R 1a is selected from the group consisting of hydrogen, C 1 -C 6 alkyl and C 1 -C 6 haloalkyl;
R 1b is selected from the group consisting of hydrogen, C 1 -C 6 alkyl, C 1 -C 3 alkoxy- and C 1 -C 6 haloalkyl; or
R 1a and R 1b together are —CH 2 CH 2 CH 2 CH 2 —, —CH 2 CH 2 CH 2 CH 2 CH 2 — or —CH 2 CH 2 OCH 2 CH 2 —; and
X is selected from the group consisting of O, —CF 2 —, —C(CH 3 )— and —CH 2 —;
m is 0, 1 or 2 wherein if X is O or —CF 2 — then m is 1 or 2;
R 2 is selected from the group consisting of hydrogen, C 1 -C 6 alkyl and C 3 -C 6 cycloalkyl;
A 1 is selected from the group consisting of O, C(O) and (CR e R f ); and
R a , R b , R c , 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.
2. The compound according to claim 1 , wherein X is selected from the group consisting of O, —CF 2 — and —CH 2 —.
3. The compound according to claim 1 , wherein X is O.
4. The compound according to claim 1 , wherein X is —CH 2 —.
5. The compound according to claim 1 , wherein R 2 is methyl.
6. The compound according to claim 1 , wherein R 1a and R 1b are both C 1 -C 6 alkyl.
7. The compound according to claim 1 , wherein A 1 is (CR e R f ).
8. The compound according to claim 1 , wherein R a , R b , R c , R d , R e and R f are hydrogen.
9. A compound according to claim 1 , wherein R a , R b , R c , R d , R e are hydrogen and R f is methyl.
10. A herbicidal composition comprising a compound according to claim 1 and an agriculturally acceptable formulation adjuvant.
11. The herbicidal composition according to claim 10 , further comprising at least one pesticide.
12. The herbicidal composition according to claim 11 , wherein the pesticide is a herbicide or herbicide safener.
13. A method of controlling weeds at a locus, comprising: applying a weed controlling amount of a composition according to claim 10 to the locus of a weed.
14. A compound of Formula (IV):
wherein
R 1a is selected from the group consisting of hydrogen, C 1 -C 6 alkyl and C 1 -C 6 haloalkyl;
R 1b is selected from the group consisting of hydrogen, C 1 -C 6 alkyl, C 1 -C 3 alkoxy- and C 1 -C 6 haloalkyl; or
R 1a and R 1b together are —CH 2 CH 2 CH 2 CH 2 —, —CH 2 CH 2 CH 2 CH 2 CH 2 — or —CH 2 CH 2 OCH 2 CH 2 —; and
X is selected from the group consisting of O, —CF 2 —, —C(CH 3 )— and —CH 2 —;
m is 0, 1 or 2 wherein if X is O or —CF 2 — then m is 1 or 2;
R 2 is selected from the group consisting of hydrogen, C 1 -C 6 alkyl and C 3 -C 6 cycloalkyl.
15. A compound of formula (I)
(I)
wherein R 1a , R 1b , R 2 , X, A, R b , R a , R c , R d , and m are defined as follows:
R 1a
R 1b
R 2
X
A = A 1
R b
R a
R c
R d
m
Me
Me
Me
CH 2
CH 2
H
H
H
H
0
Me
Me
Me
CH 2
CH 2
H
H
H
H
1
—CH 2 CH 2 OCH 2 CH 2 —
Me
CH 2
CH 2
H
H
H
H
0
—CH 2 CH 2 OCH 2 CH 2 —
Me
CH 2
CH 2
H
H
H
H
1
—CH 2 CH 2 CH 2 CH 2 —
Me
CH 2
CH 2
H
H
H
H
1
Me
H
Me
CH 2
CH 2
H
H
H
H
1
Et
Et
Me
CH 2
CH 2
H
H
H
H
1
Me
H
Me
O
CH 2
H
H
H
H
2
Me
Me
Me
O
CH 2
H
H
H
H
2
Me
Me
Me
CH 2
CH(CH 3 )
H
H
H
H
1
Me
Me
Me
CH 2
C(CH 3 ) 2
H
H
H
H
1
Me
Me
Me
CH 2
CH 2
H
—CH 2 CH 2 —
H
1
Me
Et
Me
CH 2
CH 2
H
H
H
H
1
CF 3 CH 2 —
Me
Me
CH 2
CH 2
H
H
H
H
1
Me
Me
Me
O
CH 2
H
H
H
H
2
Me
Me
cPr
CH 2
CH 2
H
H
H
H
1
Me
Me
Me
CH 2
CH 2
H
H
H
H
2
Me
Me
Me
CF 2
CH 2
H
H
H
H
1
Me
MeO—
Me
CH 2
CH 2
H
H
H
H
1
Me
CF 3 CH 2
Me
CH 2
CH(CH 3 )
H
H
H
H
1
Et
Et
Me
O
CH 2
H
H
H
H
2
Me
Et
Me
O
CH 2
H
H
H
H
2
Me
CF 3 CH 2
Me
O
CH 2
H
H
H
H
2
—CH 2 CH 2 CH 2 CH 2 —
Me
O
CH 2
H
H
H
H
2
—CH 2 CH 2 OCH 2 CH 2 —
Me
O
CH 2
H
H
H
H
2
Me
Me
Me
O
CH(CH 3 )
H
H
H
H
2
Me
Me
Me
O
C(CH 3 ) 2
H
H
H
H
2
Me
Me
Me
CH(CH 3 )
CH 2
H
H
H
H
0
Me
Me
Me
CH(CH 3 )
CH 2
H
H
H
H
0