Pyridazinone derivatives

Details Pyridazinone derivatives Pyridazinone derivatives

1999-03-23

2001-02-13

Bernhardt, Emily (Department: 1611)

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

Organic compounds

Four or more ring nitrogens in the bicyclo ring system

C544S238000, C544S237000, C504S238000, C560S168000

Reexamination Certificate

active

06187920

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to pyridazinone derivatives and the use of the said pyridazinone.
The object of the present invention is to provide compounds having excellent herbicidal activity.
SUMMARY OF THE INVENTION
The present inventor has intensely studied to seek out compounds that have excellent herbicidal activity, as a result, and has found that the pyridazinone derivatives encompassed by Chemical Formula 3 below, possess an excellent herbicidal activity, and arrived at the present invention. Accordingly, the present invention provides pyridazinone derivatives (hereinafter, the present invention compound) encompassed by the formula:
Chemical Formula 3
wherein,
R
1
represents hydrogen, halogen, C
1
-C
3
alkyl or C
1
-C
3
haloalkyl;
R
2
represents hydrogen, halogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, OR
8
, SR
9
, NHR
10
, COOR
11
, COR
12
, SO
2
R
3
, NO
2
or CN;
R
3
represents hydrogen, halogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
1
-C
3
alkoxy C
1
-C
3
alkyl, OR
8
, SR
9
, NHR
10
, COOR
11
, COR
12
, SO
2
R
13
, C(R
121
)═C(R
14
)(R
15
), NO
2
or CN;
R
4
represents hydrogen, halogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
1
-C
3
alkoxy C
1
-C
3
alkyl, OR
8
, SR
9
, NHR
10
, COOR
11
, COR
12
, SO
2
R
13
, C(R
121
)═C(R
14
)(R
15
), C(R
16
)═NOR
17
, NO
2
or CN;
R
5
represents hydrogen, halogen or C
1
-C
3
alkyl;
R
6
represents C
1
-C
3
alkyl or C
1
-C
3
haloalkyl;
R
5
and R
6
may have each end bonded to each other to form trimethylene that may be substituted with fluorine(s) or tetramethylene that may be substituted with fluorine(s);
R
7
represents hydrogen, halogen, or C
1
-C
3
alkyl; and in which;
R
8
represents hydrogen, a C
1
-C
10
alkyl, C
1
-C
10
haloalkyl, C
3
-C
8
alkenyl, C
3
-C
8
haloalkenyl, C
3
-C
8
alkynyl, C
3
-C
8
haloalkynyl, C
3
-C
10
cycloalkyl, C
3
-C
10
cyclohaloalkyl, C
3
-C
10
cycloalkenyl, C
3
-C
10
cyclohaloalkenyl, C
3
-C
10
cycloalkyl C
1
-C
3
alkyl, C
3
C
10
cyclohaloalkyl C
1
-C
3
alkyl, C
3
-C
10
cycloalkenyl C
1
-C
3
alkyl, C
3
-C
10
cyclohaloalkenyl C
1
-C
3
alkyl, C
1
-C
5
alkylcarbonyl, C
1
-C
5
haloalkylcarbonyl, C
3
-C
6
cycloalkylcarbonyl, C
3
-C
6
cyclohaloalkylcarbonyl, C
1
-C
6
alkylcarbonyl C
1
-C
6
alkyl, C
1
-C
6
haloalkylcarbonyl C
1
-C
6
alkyl, C
1
-C
6
alkoxycarbonyl, C
1
-C
6
haloalkoxycarbonyl, C
3
-C
10
cycloalkoxycarbonyl, C
3
-C
10
cyclohaloalkoxycarbonyl, C
1
-C
10
alkoxycarbonyl C
1
-C
5
alkyl, C
1
-C
10
haloalkoxycarbonyl C
1
-C
5
alkyl, C
3
-C
10
cycloalkoxycarbonyl C
1
-C
5
alkyl, C
3
-C
10
cyclohaloalkoxycarbonyl C
1
-C
5
alkyl, C
1
-C
6
alkoxy C
1
-C
6
alkyl, C
1
-C
6
haloalkoxy C
1
-C
6
alkyl, C
1
-C
6
alkylthio C
1
-C
6
alkyl, C
1
-C
6
haloalkylthio C
1
-C
6
alkyl, cyano C
1
-C
4
alkyl, aryl that may have a substituent or substituents, aryl C
1
-C
3
alkyl that may have a substituent or substituents, arylcarbonyl that may have a substituent or substituents, SO
2
R
20
, CH
2
C(═O)CO
2
R
41
, CH(CH
3
)C(═O)CO
2
R
41
, CH
2
C(═NOR
42
)CO
2
R
41
or CH(CH
3
)C(═NOR
42
)CO
2
R
41
;
R
9
represents hydrogen, C
1
-C
10
alkyl, C
1
-C
10
haloalkyl, C
3
-C
8
alkenyl, C
3
-C
8
haloalkenyl, C
3
-C
8
alkynyl, C
3
-C
8
haloalkynyl, C
3
-C
10
cycloalkyl, C
3
-C
10
cyclohaloalkyl, C
3
-C
10
cycloalkenyl, C
3
-C
10
cyclohaloalkenyl, C
3
-C
10
cycloalkyl C
1
-C
3
alkyl, C
3
-C
10
cyclohaloalkyl C
1
-C
3
alkyl, C
3
-C
10
cycloalkenyl C
1
-C
3
alkyl, C
3
-C
10
cyclohaloalkenyl C
1
-C
3
alkyl, C
1
-C
5
alkylcarbonyl, C
1
-C
5
haloalkylcarbonyl, C
3
-C
6
cycloalkylcarbonyl, C
3
-C
6
cyclohaloalkylcarbonyl, C
1
-C
6
alkylcarbonyl C
1
-C
6
alkyl, C
1
-C
6
haloalkylcarbonyl C
1
-C
6
alkyl, C
1
-C
6
alkoxycarbonyl, C
1
-C
6
haloalkoxycarbonyl, C
3
-C
10
cycloalkoxycarbonyl, C
3
-C
10
cyclohaloalkoxycarbonyl, C
1
-C
10
alkoxycarbonyl C
1
-C
5
alkyl, C
1
-C
10
haloalkoxycarbonyl C
1
-C
5
alkyl, C
3
-C
10
cycloalkoxycarbonyl C
1
-C
5
alkyl, C
3
-C
10
cyclohaloalkoxycarbonyl C
1
-C
5
alkyl, C
1
-C
6
alkoxy C
1
-C
6
alkyl, C
1
-C
6
haloalkoxy C
1
-C
6
alkyl, C
1
-C
6
alkylthio C
1
-C
6
alkyl, C
1
-C
6
haloalkylthio C
1
-C
6
alkyl, cyano C
1
-C
4
alkyl, aryl that may have a substituent or substituents, aryl C
1
-C
3
alkyl that may have a substituent or substituents, arylcarbonyl group that may have a substituent or substituents, CH
2
C(═O)CO
2
R
41
, CH(CH
3
)C(═O)CO
2
R
41
, CH
2
C(═NOR
42
)CO
2
R
41
or CH(CH
3
)C(═NOR
42
)CO
2
R
41
;
R
10
represents hydrogen, C
1
-C
10
alkyl, C
1
-C
10
haloalkyl, C
3
-C
8
alkenyl, C
3
-C
8
haloalkenyl, C
3
-C
8
alkynyl, C
3
-C
8
haloalkynyl, C
3
-C
10
cycloalkyl, C
3
-C
10
cyclohaloalkyl, C
3
-C
10
cycloalkenyl, C
3
-C
10
cyclohaloalkenyl, C
3
-C
10
cycloalkyl C
1
-C
3
alkyl, C
3
-C
10
cyclohaloalkyl C
1
-C
3
alkyl, C
3
-C
10
cycloalkenyl C
1
-C
3
alkyl, C
3
-C
10
cyclohaloalkenyl C
1
-C
3
alkyl, C
1
-C
5
alkylcarbonyl, C
1
-C
5
haloalkylcarbonyl, C
3
-C
6
cycloalkylcarbonyl, C
3
-C
6
cyclohaloalkylcarbonyl, C
1
-C
6
alkylcarbonyl C
1
-C
6
alkyl, C
1
-C
6
haloalkylcarbonyl C
1
-C
6
alkyl, C
1
-C
6
alkoxycarbonyl, C
1
-C
6
haloalkoxycarbonyl, C
3
-C
10
cycloalkoxycarbonyl, C
3
-C
10
cyclohaloalkoxycarbonyl, C
1
-C
10
alkoxycarbonyl C
1
-C
5
alkyl, C
1
-C
10
haloalkoxycarbonyl C
1
-C
5
alkyl, C
3
-C
10
cycloalkoxycarbonyl C
1
-C
5
alkyl, C
3
-C
10
cyclohaloalkoxycarbonyl C
1
-C
5
alkyl, C
1
-C
6
alkoxy C
1
-C
6
alkyl, C
1
-C
6
haloalkoxy C
1
-C
6
alkyl, C
1
-C
6
alkylthio C
1
-C
6
alkyl, C
1
-C
6
haloalkylthio C
1
-C
6
alkyl, cyano C
1
-C
4
alkyl, aryl that may have a substituent or substituents, aryl C
1
-C
3
alkyl that may have a substituent or substituents, arylcarbonyl that may have a substituent or substituents, SR
18
, SOR
19
, SO
2
R
20
, CH
2
C(═O)CO
2
R
41
, CH(CH
3
)C(═O)CO
2
R
41
, CH
2
C(═NOR
42
)CO
2
R
41
or CH(CH
3
)C(═NOR
42
)CO
2
R
41
;
R
11
represents hydrogen, C
1
-C
10
alkyl, C
1
-C
10
haloalkyl, C
3
-C
10
alkenyl, C
3
-C
10
haloalkenyl, C
3
-C
10
alkynyl, C
3
-C
10
haloalkynyl, C
3
-C
8
cycloalkyl, C
3
-C
8
cycloharoalkyl, N(R
21
)(R
22
), N═C(R
21
)(R
22
), C
1
-C
5
alkoxycarbonyl C
1
-C
3
alkyl or C
1
-C
5
haloalkoxycarbonyl C
1
-C
3
alkyl;
R
12
represents hydrogen, chlorine, C
1
-C
5
alkyl, C
1
-C
5
haloalkyl, C
3
-C
6
cycloalkyl, C
3
-C
6
cyclohaloalkyl, or N(R
23
)(R
24
);
R
13
represents chlorine, C
1
-C
10
alkyl, C
1
-C
10
haloalkyl, N(R
25
)(R
26
) or OR
27
;
R
14
represents hydrogen, halogen or C
1
-C
3
alkyl;
R
15
represents hydrogen, COOR
28
, cyano or C
1
-C
5
alkyl;
R
16
represents hydrogen, C
1
-C
4
alkyl, C
1
-C
4
haloalkyl, C
3
-C
5
cycloalkyl or C
3
-C
5
cyclohaloalkyl;
R
17
represents hydrogen, C
1
-C
10
alkyl, C
1
-C
10
haloalkyl, C
3
-C
6
cycloalkyl, C
3
-C
6
cyclohaloalkyl, C
3
-C
10
cycloalkyl C
1
-C
3
alkyl, C
3
-C
10
cyclohaloalkyl C
1
-C
3
alkyl, C
3
C
5
alkenyl, C
3
-C
5
haloalkenyl, C
3
-C
5
alkynyl, C
3
-C
5
haloalkynyl, C
1
-C
5
alkoxycarbonyl C
1
-C
3
alkyl, C
1
-C
5
haloalkoxycarbonyl C
1
-C
3
alkyl, aryl that may have a substituent or substituents or aryl C
1
-C
3
alkyl that may have a substituent or substituents;
R
18
represents C
1
-C
10
alkyl, C
1
-C
10
haloalkyl or aryl that may have a substituent or substituents;
R
19
represents C
1
-C
10
alkyl, C
1
-C
10
haloalkyl, C
3
-C
8
cycloalkyl, C
3
-C
5
cyclohaloalkyl or aryl that may have a substituent or substituents;
R
20
represents C
1
-C
10
alkyl, C
1
-C
10
haloalkyl, C
3
-C
8
cycloalkyl, C
3
-C
8
cyclohaloalkyl or aryl that may have a substituent or substituents;
R
21
represents hydrogen or C
1
-C
5
alkyl;
R
22
represents hydrogen, C
1
-C
5
alkyl, C
1
-C
5
haloalkyl or aryl that may have a substituent or substituents;
R
23
represents hydrogen, C
1
-C
10
alkyl, C
1
-C
10
haloalkyl, C
3
-C
10
cycloalkyl, C
3
-C
10
cyclohaloalkyl or aryl that may have a substituent or substituents;
R
24
represents hydrogen, C
1
-C
10
alkyl or C
1
-C
10
haloalkyl;
R
25
repre

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