Pyridone derivatives and herbicides

Details Pyridone derivatives and herbicides Pyridone derivatives and herbicides

2001-05-10

2002-10-29

Rotman, Alan L. (Department: 1625)

Plant protecting and regulating compositions

Plant growth regulating compositions

Plural active ingredients

C546S300000, C546S301000, C546S303000, C504S116100

Reexamination Certificate

active

06472348

ABSTRACT:

TECHNICAL FIELD
The present invention relates to pyridone derivatives and herbicides containing them as active ingredients.
BACKGROUND ART
Heretofore, some 3-(substituted)phenyl-2-pyridone derivatives have been known. However, no more than a few compounds have been known with respect to 3-(substituted)phenyl-6-(substituted)alkyl-2-pyridone derivatives, which represent the characteristic of the compounds of the present invention. For example, the specification of JP-B-46-30190 discloses 3-(4-chlorophenyl)-6-methyl-2-pyridone. Further, U.S. Pat. No. 3,720,768 discloses 3-phenyl-6-ethyl-2-pyridone. However, either specification discloses nothing about herbicidal activities. On the other hand, some 3-(substituted)phenyl-4-pyridone derivatives have been known. However, no more than a few compound have been known with respect to 3-(substituted)phenyl-6-(substituted)alkyl-4-pyridone derivatives, which represent the characteristic of the compounds of the present invention. For example, Chemical Abstract vol. 76, No. 140407, discloses 3-phenyl-6-methyl-4-pyridone, but discloses nothing about the herbicidal activities. Further, the specification of JP-A-62-167708 discloses a 3-(substituted)phenyl-6-(substituted)alkyl-4-pyridone derivative having a carbamoyl group at the 5-position, and a herbicidal activity is also disclosed. However, it is different from the compounds of the present invention.
In recent years, a herbicide is strongly desired which has selective activities to kill only weeds without giving adverse effects to crop plants even when it is applied to the crop plants and weeds simultaneously. Further, it is desired to develop an agent whereby complete effects can be obtained at a low dose, in order to prevent the agent from remaining excessively in the environment.
To solve the above problems, the present inventors have synthesized many pyridone derivatives and conducted various studies on their usefulness. As a result, it has been found that certain pyridone derivatives have excellent herbicidal activities and selectivity to solve the above problems, and the present invention has been accomplished.
DISCLOSURE OF THE INVENTION
Namely, the present invention provides a pyridone derivative represented by the general formula:
{wherein R is a C
1
-C
6
alkyl group or a C
1
-C
6
haloalkyl group, R
1
is a hydrogen atom, a C
1
-C
6
alkyl group, a C
1
-C
6
haloalkyl group, an acetyl group, a group of —N═CR
13
R
14
or a group of —NR
23
R
24
(provided that when R
1
is a hydrogen atom, R is a C
1
-C
6
haloalkyl group), each of R
13
and R
14
which are independent of each other, is a hydrogen atom, a C
1
-C
6
alkyl group, a group of —NR
23
R
24
or a phenyl group (said group may be substituted by a halogen atom, a nitro group, a C
1
-C
6
alkyl group, a C
1
-C
6
haloalkyl group or a C
1
-C
6
alkoxy group), each of R
23
and R
24
which are independent of each other, is a hydrogen atom, a C
1
-C
6
alkyl group, a C
1
-C
6
haloalkyl group, a C
1
-C
6
alkylcarbonyl group, a C
1
-C
6
alkoxycarbonyl group, a benzoyl group (said group may be substituted by a halogen atom, a nitro group, a C
1
-C
6
alkyl group, a C
1
-C
6
haloalkyl group or a C
1
-C
6
alkoxy group), a phenoxycarbonyl group (said group may be substituted by a halogen atom, a nitro group, a C
1
-C
6
alkyl group, a C
1
-C
6
haloalkyl group or a C
1
-C
6
alkoxy group), a formyl group or a C
1
-C
6
alkylsulfonyl group, R
2
is a hydrogen atom, a C
1
-C
6
alkyl group, a carboxyl group or a C
1
-C
6
alkoxycarbonyl group, R
19
is a hydrogen atom, a halogen atom, a C
1
-C
6
alkoxy group, a cyano group or a C
1
-C
6
alkyl group, and Q represents a formula of
[wherein R
3
is a hydrogen atom or a halogen atom, R
4
is a hydrogen atom, a halogen atom, a nitro group, a C
1
-C
6
alkoxycarbonyl C
1
-C
6
alkoxy group, a C
1
-C
6
alkoxycarbonyl C
1
-C
6
alkylthio group, a C
1
-C
6
alkoxycarbonyl C
1
-C
6
alkylamino group, a benzyloxy group (said group may be substituted by a halogen atom, a nitro group, a C
1
-C
6
alkyl group or a C
1
-C
6
alkoxy group), a hydroxyl group, a thiol group, an amino group or a cyano group, R
5
is a hydrogen atom, a halogen atom, a C
1
-C
6
alkyl group, a C
2
-C
6
alkenyl group, a C
1
-C
6
haloalkyl group, a hydroxyl group, a thiol group, an amino group, a nitro group, a chlorosulfonyl group, an acetylthio group, a cyano group, a cyano C
1
-C
6
alkyl group, a formyl group, a hydroxymethyl group, a group of —YR
9
, a group of —CR
21
═NOR
9
, a group of —CO
2
R
10
, a group of —COSR
10
, a group of —CONR
10
R
11
, a group of —SO
2
NR
10
R
11
, a group of —NHCONHR
11
, a group of —SOR
12
, a group of —SO
2
R
12
, an acyl group, a C
1
-C
6
alkoxy C
1
-C
6
alkyl group, a group of —CO
2
N═CR
13
R
14
, a group of —CH(OH)R
21
, a group of —CH
2
YR
9
, a hetero ring group or a group of —CH
2
CH(Cl)CO
2
R
10
, Y is an oxygen atom, a sulfur atom or a group of —NR
21
—, R
21
is a hydrogen atom, a C
1
-C
6
alkyl group, a C
3
-C
6
alkenyl group or a C
3
-C
6
alkynyl group, R
9
is a C
1
-C
6
alkyl group, a C
3
-C
6
alkenyl group, a C
3
-C
6
alkynyl group, a C
3
-C
8
cycloalkyl group, a C
1
-C
6
haloalkyl group, a hydroxy C
1
-C
6
alkyl group, a C
3
-C
6
haloalkenyl group, a C
3
-C
8
cycloalkyl C
1
-C
6
alkyl group, a C
1
-C
6
alkoxy C
1
-C
6
alkyl group, a C
1
-C
6
alkoxycarbonyl group, a C
1
-C
6
alkylsulfonyl group, a C
1
-C
6
haloalkylsulfonyl group, a C
1
-C
6
alkylthio C
1
-C
6
alkyl group, a C
1
-C
6
alkylsulfinyl C
1
-C
6
alkyl group, a C
1
-C
6
alkylsulfonyl C
1
-C
6
alkyl group, a cyano C
1
-C
6
alkyl group, a group of —CH(R
15
)COYR
16
, a benzyl group (said group may be substituted by a halogen atom, a nitro group, a C
1
-C
6
alkyl group, a C
1
-C
6
haloalkyl group or a C
1
-C
6
alkoxy group), a group of —CH
2
(3-6 membered hetero ring) (the hetero ring group of said group may be substituted by a halogen atom, a nitro group, an oxo group, a C
1
-C
6
alkyl group, a C
1
-C
6
haloalkyl group or a C
1
-C
6
alkoxy group), a 3-6 membered hetero ring group (said group may be substituted by a halogen atom, a nitro group, an oxo group, a C
1
-C
6
alkyl group, a C
1
-C
6
haloalkyl group or a C
1
-C
6
alkoxy group) or a phenyl group (said group may be substituted by a halogen atom, a nitro group, a C
1
-C
6
alkyl group, a C
1
-C
6
haloalkyl group or a C
1
-C
6
alkoxy group), R
15
is a hydrogen atom, a C
1
-C
6
alkyl group or a C
3
-C
8
cycloalkyl group, R
16
is a hydrogen atom, a c
1
-C
6
alkyl group, a C
3
-C
6
alkenyl group, a C
3
-C
6
alkynyl group, a C
3
-C
8
cycloalkyl group, a C
1
-C
6
haloalkyl group, a C
3
-C
6
haloalkenyl group, a C
3
-C
8
cycloalkyl C
1
-C
6
alkyl group, a C
1
-C
6
alkoxy C
1
-C
6
alkyl group, a C
1
-C
6
alkylthio C
1
-C
6
alkyl group, a C
1
-C
6
alkylsulfinyl C
1
-C
6
alkyl group, a C
1
-C
6
alkylsulfonyl C
1
-C
6
alkyl group, a benzyl group (said group may be substituted by a halogen atom, a nitro group, a C
1
-C
6
alkyl group, a C
1
-C
6
haloalkyl group or a C
1
-C
6
alkoxy group) or a phenyl group (said group may be substituted by a halogen atom, a nitro group, a C
1
-C
6
alkyl group, a C
1
-C
6
haloalkyl group, a C
1
-C
6
alkoxycarbonyl C
1
-C
6
alkyl group or a C
1
-C
6
alkoxy group), R
10
is a hydrogen atom, a sodium atom, a C
1
-C
6
alkyl group, a C
3
-C
6
alkenyl group, a C
3
-C
6
alkynyl group, a C
3
-C
8
cycloalkyl group, a C
1
-C
6
haloalkyl group, a C
3
-C
6
haloalkenyl group, a C
3
-C
8
cycloalkyl C
1
-C
6
alkyl group, a C
1
-C
6
alkoxy C
1
-C
6
alkyl group, a C
1
-C
6
alkylthio C
1
-C
6
alkyl group, a C
1
-C
6
alkylsulfinyl C
1
-C
6
alkyl group, a C
1
-C
6
alkylsulfonyl C
1
-C
6
alkyl group, a C
1
-C
6
alkoxycarbonyl C
1
-C
6
alkyl group, a C
3
-C
6
alkenyloxycarbonyl C
1
-C
6
alkyl group, a C
3
-C
6
alkynyloxycarbonyl C
1
-C
6
alkyl group, a C
3
-C
8
cycloalkyloxycarbonyl C
1
-C
6
alkyl group, a C
1
-C
6
alkoxy C
1
-C
6
alkoxycarbonyl C
1
-C
6
alkyl group, a halo C
1
-C
6
alkoxycarbonyl C
1
-C
6
alkyl group, a halo C
3
-C
6

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