Pyridazin-3-one derivatives, their use, and intermediates...

Details Pyridazin-3-one derivatives, their use, and intermediates... Pyridazin-3-one derivatives, their use, and intermediates...

2000-03-07

2002-02-19

Bernhardt, Emily (Department: 1624)

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

C544S159000, C544S162000, C546S226000, C546S231000, C548S540000, C548S566000

Reexamination Certificate

active

06348628

ABSTRACT:

TECHNICAL FIELD
The present invention relates to pyridazin-3-one derivatives, their use as herbicides, and intermediates for their production.
BACKGROUND ART
EP-A-0029123 discloses a process for the preparation of substituted anilines and novel substituted anilines. In particular, it teaches that certain substituted anilines obtained by this process are useful as important starting materials for the preparation of novel substituted pyridazin-3-one derivatives having herbicidal activity in postemergence application. These pyridazin-3-one derivatives are, however, different from those of the present invention in that they have a substituted phenoxyphenyl group as an essential structural element at position 2 of the pyridazinone ring and further have quite distinct substituents on the pyridazinone ring.
DISCLOSURE OF INVENTION
The present inventors have intensively studied to find a compound having excellent herbicidal activity. As a result, they have found that pyridazin-3-one derivatives represented by formula [1] as depicted below have excellent herbicidal activity, thereby completing the present invention.
Thus the present invention provides a compound of the formula:
wherein R
1
is C
1
-C
3
haloalkyl; R
2
and R
3
are the same or different and are hydrogen, C
1
-C
3
alkyl, C
1
-C
3
haloalkyl, or C
1
-C
3
alkoxy C
l
-C
3
alkyl; and Q is [Q-1], [Q-2], [Q-3], [Q-4], or [Q-5] of the formula:
wherein
X is hydrogen or halogen;
Y is halogen, nitro, cyano, or trifluoromethyl;
Z
1
is oxygen, sulfur, or NH;
Z
2
is oxygen or sulfur;
n is 0 or 1;
B is hydrogen, halogen, nitro, cyano, chlorosulfonyl, OR
10
, SR
10
, SO
2
—OR
10
, N(R
11
)R
12
, SO
2
N(R
11
)R
12
, NR
11
(COR
13
), NR
11
(SO
2
R
14
), N(SO
2
R
14
)—(SO
2
R
15
), N(SO
2
R
14
)(COR
13
), NHCOOR
13
, COOR
10
, CON(R
11
)R
12
, CSN(R
11
)R
12
, COR
16
, CR
17
═CR
18
COR
16
, CR
17
═CR
18
COOR
13
, CR
17
═CR
18
CON(R
11
)R
12
, CH
2
CH—WCOOR
13
, CH
2
CHWCON(R
11
)R
12
, CR
17
═NOR
33
, CR
17
═NN(R
11
)R
12
, CR
17
(Z
2
—R
34
)
2
, OCO
2
R
19
, or OCOR
19
;
R
4
is hydrogen or C
1
-C
3
alkyl;
R
5
is hydrogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
3
-C
8
cycloalkylalkyl, C
3
-C
6
alkenyl, C
3
-C
6
haloalkenyl, C
3
-C
6
alkynyl, C
3
-C
6
haloalkynyl, cyano C
1
-C
6
alkyl, C
2
-C
8
alkoxyalkyl, C
3
-C
8
alkoxyalkoxyalkyl, carboxy C
1
-C
6
alkyl, (C
1
-C
6
alkoxy)-carbonyl C
1
-C
6
alkyl, {(C
1
-C
4
alkoxy) C
1
-C
4
alkoxyl}carbonyl C
1
-C
6
alkyl, (C
3
-C
8
cycloalkoxy)carbonyl C
1
-C
6
alkyl, CH
2
CON(R
11
)R
12
, CH
2
COON(R
11
)R
12
, CH(C
1
-C
4
alkyl)CON(R
11
)R
12
, CH(C
1
-C
4
alkyl)COON(R
11
)R
12
, C
2
-C
8
alkylthioalkyl, or hydroxy C
1
-C
6
alkyl;
R
6
is C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, formyl, cyano, carboxyl, hydroxy C
1
-C
6
alkyl, C
1
-C
6
alkoxy C
1
-C
6
alkyl, C
1
-C
6
alkoxy C
1
-C
6
alkoxy C
1
-C
6
alkyl, (C
1
-C
6
alkyl)carbonyloxy C
1
-C
6
alkyl, (C
1
-C
6
haloalkyl)carbonyloxy C
1
-C
6
alkyl, (C
1
-C
6
alkoxy)carbonyl, or (C
1
-C
6
alkyl)carbonyl;
R
7
is hydrogen or C
1
-C
6
alkyl; and
R
8
is hydrogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, hydroxy C
1
-C
6
alkyl, C
2
-C
8
alkoxyalkyl, C
3
-C
10
alkoxyalkoxyalkyl, (C
1
-C
5
alkyl)carbonyloxy C
1
-C
6
alkyl, (C
1
-C
6
haloalkyl)carbonyloxy C
1
-C
6
alkyl, carboxyl, carboxy C
1
-C
6
alkyl, (C
1
-C
8
alkoxy)carbonyl, (C
1
-C
6
haloalkoxy)carbonyl, (C
3
-C
10
cycloalkoxy)carbonyl, (C
3
-C
8
alkenyloxy)carbonyl, (C
3
-C
8
alkynyloxy)carbonyl, aminocarbonyl, (C
1
-C
6
alkyl)aminocarbonyl, di(C
1
-C
6
alkyl)aminocarbonyl, (C
1
-C
6
alkyl)aminocarbonyloxy C
1
-C
6
alkyl, or di(C
1
-C
6
alkyl)aminocarbonyloxy C
1
-C
6
alkyl;
wherein R
10
is hydrogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
3
-C
8
cycloalkyl, benzyl, C
3
-C
6
alkenyl, C
3
-C
6
haloalkenyl, C
3
-C
6
alkynyl, C
3
-C
6
haloalkynyl, cyano C
1
-C
6
alkyl, C
2
-C
8
alkoxyalkyl, C
2
-C
8
alkylthioalkyl, carboxy C
1
-C
6
alkyl, (C
1
-C
8
alkoxy)carbonyl C
1
-C
6
alkyl, (C
1
-C
6
haloalkoxy)carbonyl C
1
-C
6
alkyl, {(C
1
-C
4
alkoxy) C
1
-C
4
alkoxy}carbonyl C
1
-C
6
alkyl, (C
3
-C
8
cycloalkoxy)carbonyl C
1
-C
6
alkyl, (C
1
-C
6
alkyl)carbonyl C
1
-C
6
alkyl, (C
1
-C
6
haloalkyl)carbonyl C
1
-C
6
alkyl, {(C
1
-C
4
alkoxy) C
1
-C
4
alkyl}carbonyl C
1
-C
6
alkyl, (C
3
-C
8
cycloalkyl)carbonyl C
1
-C
6
alkyl, CH
2
CON—(R
11
)R
12
, CH
2
COON(R
11
)R
12
, CH(C
1
-C
4
alkyl)CON(R
11
)R
12
, CH(C
1
-C
4
alkyl)—COON(R
11
)R
12
, {(C
1
-C
6
alkoxy)carbonyl C
1
-C
6
alkyl}oxycarbonyl C
1
-C
6
alkyl, or hydroxy C
1
-C
6
alkyl;
R
11
and R
12
are independently hydrogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
3
-C
6
alkenyl, C
3
-C
6
alkynyl, cyano C
1
-C
6
alkyl, C
2
-C
8
alkoxyalkyl, C
2
-C
8
alkylthioalkyl, carboxy C
1
-C
6
alkyl, (C
1
-C
6
alkoxy)carbonyl C
1
-C
6
alkyl, (C
3
-C
8
cycloalkoxy)carbonyl C
1
-C
6
alkyl, {(C
1
-C
4
alkoxy) C
1
-C
4
alkoxy}carbonyl C
1
-C
6
alkyl, or R
11
and R
12
are combined together to form tetramethylene, pentamethylene, or ethyleneoxy-ethylene;
R
13
is hydrogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
3
-C
8
cycloalkyl, or C
3
-C
6
alkenyl;
R
14
and R
15
are independently C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, or phenyl optionally substituted with methyl or nitro;
R
16
is hydrogen, 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
2
-C
8
alkoxyalkyl, or hydroxy C
1
-C
6
alkyl;
R
17
and R
18
are independently hydrogen or C
1
-C
6
alkyl;
R
19
is C
1
-C
6
alkyl;
R
33
is hydrogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
3
-C
8
cycloalkyl, C
3
-C
6
alkenyl, C
3
-C
6
haloalkenyl, C
3
-C
6
alkynyl, C
3
-C
6
haloalkynyl, cyano C
1
-C
6
alkyl, or (C
1
-C
6
alkoxy)carbonyl C
1
-C
6
alkyl;
R
34
is C
1
-C
6
alkyl, or two R
34
's are combined together to form (CH
2
)
2
or (CH
2
)
3
; and
W is hydrogen, chlorine, or bromine, (hereinafter referred to as the present compound(s)); and a herbicide containing it as an active ingredient.
The present invention also provides a compound of the formula:
wherein R
3
is as defined above, and Q
1
is [Q
1
-1], [Q-2], [Q
1
-3], [Q-4], or [Q-5] of the formula:
wherein X, Y, Z
1
, Z
2
, n, R
4
, R
5
, R
7
, and R
8
are as defined above; B
1
is hydrogen, halogen, nitro, cyano, OR
27
, SR
27
, SO
2
OR
27
, NR
11
(R
12
), SO
2
NR
11
(R
12
), NR
11
—(COR
13
), NR
11
(SO
2
R
14
), N(SO
2
R
14
)(SO
2
R
15
), N(SO
2
R
14
)(COR
13
), NHCOOR
13
, COOR
27
, CONR
11
(R
12
), CSNR
11
(R
12
), CR
17
═CR
18
COOR
13
, CR
17
═CR
18
CONR
11
—(R
12
), CH
2
CHWCOOR
13
, CH
2
CHWCONR
11
(R
12
), CR
17
═NOR
33
, CR
17
═NNR
11
—(R
12
), CR
17
(Z
2
R
34
)
2
, OCO
2
R
19
, or OCOR
19
; R
9
is C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, cyano, carboxyl, hydroxy C
1
-C
6
alkyl, C
1
-C
6
alkoxy C
1
-C
6
alkyl, C
1
-C
6
alkoxy C
1
-C
6
alkoxy C
1
-C
6
alkyl, (C
1
-C
6
alkyl)carbonyloxy C
1
-C
6
alkyl, (C
1
-C
6
haloalkyl)carbonyloxy C
1
-C
6
alkyl, (C
1
-C
6
alkoxy)carbonyl, or (C
1
-C
6
alkyl)carbonyl; wherein R
19
is as defined above; R
27
is hydrogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
3
-C
8
cycloalkyl, benzyl, C
3
-C
6
alkenyl, C
3
-C
6
haloalkenyl, C
3
-C
6
alkynyl, C
3
-C
6
haloalkynyl, cyano C
1
-C
6
alkyl, C
2
-C
8
alkoxyalkyl, C
2
-C
8
alkylthioalkyl, carboxy C
1
-C
6
alkyl, (C
1
-C
8
alkoxy)carbonyl C
1
-C
6
alkyl, (C
1
-C
6
haloalkoxy)carbonyl C
1
-C
6
alkyl, {(C
1
-C
4
alkoxy) C
1
-C
4
alkoxy}carbonyl C
1
-C
6
alkyl, (C
3
-C
8
cycloalkoxy)carbonyl C
1
-C
6
alkyl, CH
2
CON(R
11
)R
12
, CH
2
COON(R
11
)R
12
, CH(C
1
-C
4
alkyl)CON(R
11
)R
12
, CH(C
1
-C
4
alkyl)COON(R
11
)R
12
, {(C
1
-C
6
alkoxy)carbonyl C
1
-C
6
alkyl}oxycarbonyl C
1
-C
6
alkyl, or hydroxy C
1
-C
6
alkyl; and R
11
, R
12
, R
13
, R
14
, R
15
, R
17
, R
18
, R
19
, R
33
, R
34
, and Z
2
are as defined above.
In the above de

Affiliated with

Also associated with

Rating

Pyridazin-3-one derivatives, their use, and intermediates... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Pyridazin-3-one derivatives, their use, and intermediates..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Pyridazin-3-one derivatives, their use, and intermediates... will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2943212