Pyrimidin-4-one derivatives, their use, intermediates for...

Details Pyrimidin-4-one derivatives, their use, intermediates for... Pyrimidin-4-one derivatives, their use, intermediates for...

2000-05-31

2001-06-05

Raymond, Richard L. (Department: 1624)

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

Organic compounds

Nitriles

C560S009000, C560S047000, C560S055000, C560S083000, C558S389000, C558S396000, C558S398000, C558S399000, C558S406000, C558S409000, C558S410000, C564S442000, C568S025000, C568S663000

Reexamination Certificate

active

06242634

ABSTRACT:

TECHNICAL FIELD
The present invention relates to pyrimidin-4-one derivatives, their use, intermediates for their production, and processes for producing these intermediates.
DISCLOSURE OF INVENTION
The present inventors have intensively studied to find a compound having excellent herbicidal activity. As a result, they have found that pyrimidin-4-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 hydrogen or C
1
-C
3
alkyl; R
2
is C
1
-C
3
alkyl optionally substituted with one or more halogen atoms; R
3
is C
1
-C
6
alkyl optionally substituted with one or more halogen atoms, C
3
-C
6
alkenyl, or C
3
-C
6
alkynyl; and Q is substituted phenyl (herein-after referred to as the present compound(s)); and a herbicide containing it as an active ingredient.
The present invention also provides a process for producing compound [1], which comprises reacting a compound of the formula:
wherein Q, R
1
, and R
2
are as defined above, with a compound of the formula:
 R
3
-D  [3]
wherein D is chlorine, bromine, iodine, methanesulfonyloxy, trifluoromethanesulfonyloxy, or p-toluenesulfonyloxy; and R
3
is as defined above.
The present invention further provides a compound of the formula:
wherein Q and R
1
are as defined above; R
21
is C
1
-C
3
alkyl substituted with one or more halogen atoms, which is useful as an intermediate for the production of some of the present compounds; and a process for producing a compound of the formula:
wherein Q, R
1
, and R
2
are as defined above, which comprises reacting a compound of the formula:
wherein R
19
and R
20
are independently C
1
-C
3
alkyl, and Q and R
1
are as defined above, with a compound of the formula:
wherein R
2
is as defined above.
The compound [2] may be present as a compound of the formula:
which is a tautomer thereof.
Examples of Q in the present invention include [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, NH, or methylene;
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
10
)R
11
, —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
13
, —CON(R
11
)R
12
, —CSN—(R
11
)R
12
, —COR
16
, —CR
17
═CR
18
CHO, —CR
17
═CR
18
COOR
13
, CR
17
═CR
18
CON—(R
11
)R
12
, —CH
2
CHCOOR
13
, or —CH
2
CHWCON(R
11
)R
12
, wherein W is hydrogen, chlorine, or bromine; R
10
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, 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
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,
or —CH(C
1
-C
4
alkyl)COON(R
11
)R
12
; 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, or {(C
1
-C
4
alkoxy) C
1
-C
4
alkoxy}carbonyl C
1
-C
6
alkyl, or R
11
and R
12
are taken together to form tetramethylene, pentamethylene, or ethyleneoxyethylene; R
13
is hydrogen, C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, or C
3
-C
8
cycloalkyl; 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; and R
17
and R
18
are independently hydrogen or C
1
-C
6
alkyl;
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
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
alkoxy}carbonyl C
1
-C
6
alkyl, (C
3
-C
8
cycloalkoxy)carbonylC
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
8
alkylthioalkyl, C
1
-C
6
alkylsulfonyl, C
1
-C
6
haloalkylsulfonyl, (C
1
-C
8
alkyl)carbonyl, (C
1
-C
8
alkoxy)carbonyl, 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 C
1
-C
6
alkyl, C
1
-C
6
haloalkyl, C
1
-C
6
hydroxyalkyl, 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.
In the above definition of the present compounds, the respective substituents are exemplified as follows:
Examples of the C
1
-C
3
alkyl represented by R
1
include methyl, ethyl, and isopropyl.
Examples of the C
1
-C
3
alkyl optionally substituted with one or more halogen atoms, which is represented by R
2
, include methyl, ethyl, isopropyl, trichloromethyl, trifluoromethyl, difluoromethyl, chlorodifluoromethyl, and pentafluoroethyl.
Examples of the C
1
-C
6
alkyl optionally substituted with one or more halogen atoms, which is represented by R
3
, include methyl, ethyl, isopropyl, difluoromethyl, and bromodifluoromethyl.
Examples of the C
3
-C
6
alkenyl represented by R
3
include allyl and 1-methyl-2-propenyl.
Examples of the C
3
-C
6
alkynyl represented by R
3
include propargyl and 1-methyl-2-propynyl.
In the formulas [Q-1], [Q-2], [Q-3], [Q-4], and [Q-5], the respective substituents are exemplified as follows:
Examples of the halogen represented by X, Y, and B include chlorine, fluorine, bromine, and iodine.
Examples of the C
1
-C
6
alkyl represented by R
10
include methyl, ethyl, isopropyl, propyl, isobutyl, butyl, t-butyl, amyl, isoamyl, and t-amyl.
Examples of the C
1
-C
6
haloalkyl represented by R
10
include difluoromethyl, tetrafluoroethyl, and 2,2,2-trifluoroethyl.
Examples of the C
3
-C
8
cycloalkyl represented by R
10
include cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.
Examples of the C
3
-C
6
alkenyl represented by R
10
include allyl, 1-methyl-2-propenyl, 3-butenyl, 2-butenyl, 3-methyl-2-butenyl, and 2-methyl-3-butenyl.
Examples of the C
3
-C
6
haloalkenyl represented by R
10
include 2-chloro-2-propenyl and 3,3-dichloro-2-propenyl.
Examples of the C
3
-C
6
alkynyl represented by R
10
include propargyl, 1-methyl-2-propynyl, 2-butynyl, and 1,1-dimethyl-2-propynyl.
Examples of the C
3
-C
6
haloalkynyl represented by R
10
include 3-bromo-2-propynyl.
Examples of the cyano C
1
-C
6
alkyl represented by R
10
include cyanomethyl.
Examples of the C
2
-C
8
alkoxyalkyl represented by R
1

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