Pyrimidine derivatives and herbicides containing them

Details Pyrimidine derivatives and herbicides containing them Pyrimidine derivatives and herbicides containing them

2002-03-11

2004-10-19

Raymond, Richard L. (Department: 1624)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C504S225000, C544S297000, C544S298000, C544S315000, C514S256000, C514S269000, C514S274000

Reexamination Certificate

active

06806230

ABSTRACT:

TECHNICAL FIELD
The present invention relates to novel pyrimidine derivatives and herbicides containing them as active ingredients.
BACKGROUND ART
Pyrimidine derivatives are known, for example, by the specification of international application WO95/12582, the specification of international application WO96/22980 and the specification of international application WO97/12877. However, the pyrimidine derivatives of the present invention have not been known.
A herbicide to be used for crop plants is desired to be a chemical which exhibits a sufficient herbicidal effect at a low dose and yet provides selectivity between crop plants and weeds, when applied to an upland field or to a paddy field. Accordingly, it is an object of the present invention to provide a compound which has an excellent herbicidal activity and selectivity between crop plants and weeds.
DISCLOSURE OF THE INVENTION
Under these circumstances, the present inventors have synthesized various substituted pyrimidine derivatives and have studied their physiological activities. As a result, it has been found that novel substituted pyrimidine derivatives as the compounds of the present invention have excellent herbicidal activities and selectivity between crop plants and weeds, and the present invention has been accomplished. Namely, the present invention provides a pyrimidine derivative represented by the formula (I)
wherein R
1
is a hydrogen atom (except for a case where R
2
=hydrogen atom, and W═SO
2
), a halogen atom, a C
1
-C
6
alkyl group, a C
1
-C
6
alkylcarbonyl C
1
-C
6
alkyl group, a hydroxyl group, a C
2
-C
6
alkenyl group, a C
2
-C
6
alkynyl group, a C
3
-C
6
cycloalkyl group (this group may be substituted by a halogen atom, a C
1
-C
6
alkyl group, a C
1
-C
6
alkoxy group or a C
1
-C
4
haloalkyl group), a C
1
-C
4
haloalkyl group, a C
1
-C
6
alkoxy group, a C
1
-C
4
haloalkoxy group, a C
2
-C
6
alkenyloxy group, a C
2
-C
6
alkynyloxy group, a C
3
-C
6
cycloalkyloxy group, a phenyl group (this group may be substituted by a halogen atom, a C
1
-C
6
alkyl group, a C
1
-C
6
alkoxy group, a C
1
-C
4
haloalkyl group, a C
1
-C
4
haloalkoxy group, a cyano group, a cyano C
1
-C
6
alkyl group, a nitro group, a C
1
-C
6
alkylthio group, a C
1
-C
6
alkylsulfinyl group or a C
1
-C
6
alkylsulfonyl group), a C
1
-C
6
alkylthio group (except for a case where R
2
=phenyl group, and W═SO
2
), a C
2
-C
6
alkenylthio group, a C
2
-C
6
alkynylthio group, a C
3
-C
6
cycloalkylthio group, a C
1
-C
6
alkylsulfinyl group, a C
2
-C
6
alkenylsulfinyl group, a C
2
-C
6
alkynylsulfinyl group, a C
3
-C
6
cycloalkylsulfinyl group, a C
1
-C
6
alkylsulfonyl group, a C
2
-C
6
alkenylsulfonyl group, a C
2
-C
6
alkynylsulfonyl group, a C
3
-C
6
cycloalkylsulfonyl group, a C
1
-C
6
hydroxyalkyl group, a C
2
-C
7
acyl group, a C
1
-C
6
alkoxy C
1
-C
6
alkyl group, a cyano group, a C
1
-C
6
alkoxycarbonyl group, a C
1
-C
6
alkoxycarbonyl C
1
-C
6
alkyl group, a C
1
-C
6
alkoxycarbonyl C
2
-C
6
alkenyl group, a carboxyl group, a carboxyl C
1
-C
6
alkyl group, a di C
1
-C
6
alkoxy C
1
-C
6
alkyl group, a C
1
-C
6
alkoxyimino C
1
-C
6
alkyl group, a hydroxyimino C
1
-C
6
alkyl group, a dioxolanyl group (this group may be substituted by a C
1
-C
6
alkyl group), an aldehyde group, an oxiranyl group, a NR
9
R
10
group or a CONR
9
R
10
group, R
9
is a hydrogen atom, a C
1
-C
6
alkyl group, a C
2
-C
6
alkenyl group, a C
2
-C
6
alkynyl group, a C
1
-C
4
haloalkyl 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
3
-C
6
cycloalkyl group, a C
2
-C
7
acyl group or a C
1
-C
6
alkylsulfonyl group, R
10
is a C
1
-C
6
alkyl group, a C
2
-C
6
alkenyl group, a C
2
-C
6
alkynyl group, a C
1
-C
4
haloalkyl 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
3
-C
6
cycloalkyl group, a C
2
-C
7
acyl group, a C
1
-C
6
alkylsulfonyl group, a C
1
-C
6
alkoxycarbonyl group or a benzyloxycarbonyl group, here R
9
and R
10
may, together with the carbon atom to which they are bonded, form a 5- to 7-membered saturated ring, R
2
is a hydrogen atom, a C
1
-C
6
alkyl group, a C
2
-C
6
alkenyl group, a C
2
-C
6
alkynyl group, a C
1
-C
6
alkylthio group, a C
1
-C
4
haloalkyl group, a C
1
-C
6
alkoxy 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
3
-C
6
cycloalkyl group (this group may be substituted by a halogen atom, a C
1
-C
6
alkyl group, a C
1
-C
6
alkoxy group or a C
1
-C
4
haloalkyl group), a C
2
-C
7
acyl group, a cyano group, a di C
1
-C
6
alkoxy C
1
-C
6
alkyl group, a C
1
-C
6
alkoxyimino C
1
-C
6
alkyl group, a hydroxyimino C
1
-C
6
alkyl group, a dioxolanyl group (this group may be substituted by a C
1
-C
6
alkyl group), a cyano C
1
-C
6
alkyl group, a C
1
-C
6
hydroxyalkyl group, a C
1
-C
6
alkoxycarbonyl group, a C
1
-C
6
alkoxycarbonyl C
1
-C
6
alkyl group, a CR
11
R
12
NR
9
R
10
group, a CONR
9
R
10
group, a CR
11
R
12
CONR
9
R
10
group or a group represented by any one of the formulae R
2
-1 to R
2
-13:
(wherein X is a hydrogen atom, a halogen atom, a C
1
-C
6
alkyl group, a C
2
-C
6
alkenyl group, a C
2
-C
6
alkynyl group, a C
1
-C
6
alkoxy group, a C
1
-C
6
alkoxy C
1
-C
6
alkyl group, a NR
9
R
10
group, a CONR
9
R
10
group, a C
1
-C
4
haloalkoxy group, a C
2
-C
6
alkenyloxy group, a C
3
-C
6
cycloalkyloxy group, a s C
2
-C
7
acyl group, a C
1
-C
6
alkoxycarbonyl group, a C
1
-C
6
alkylthio group, a C
1
-C
6
alkylsulfinyl group, a C
1
-C
6
alkylsufonyl group, a cyano group, a nitro group or a C
1
-C
4
haloalkyl group, n is an integer of from 1 to 3, when n is an integer of 2 or 3, the plurality of X may be the same or different, and two adjacent lower alkoxy groups may be bonded to each other to form a C
1
-C
3
alkylenedioxy group), each of R
11
and R
12
is a hydrogen atom, a C
1
-C
6
alkyl group, a C
2
-C
6
alkenyl group, a C
2
-C
6
alkynyl group or a C
1
-C
6
alkoxy group, R
3
is a hydrogen atom, a C
1
-C
6
alkyl group, a C
2
-C
6
alkenyl group, a C
2
-C
6
alkynyl group, a C
1
-C
6
alkoxy group, a di C
1
-C
6
alkylamino group, a C
3
-C
6
cycloalkyl group, a C
1
-C
6
alkoxy C
1
-C
6
alkyl group, a cyano C
1
-C
6
alkyl group, a C
3
-C
6
cycloalkyl C
1
-C
6
alkyl group, an oxiranyl C
1
-C
6
alkyl group or a C
1
-C
6
alkoxycarbonyl C
1
-C
6
alkyl group, W is a —C(═Q)Z— group or a —SO
2
— group, Q is an oxygen atom or a sulfur atom, Z is an oxygen atom, a sulfur atom, a —NR
6
— group, a —CH
2
CH
2
— group, a —CH═CH— group, a —C(R
4
)R
5
— group, a —C(R
4
)R
5
—Q— group, a —Q—C(R
4
)R
5
— group, a —C(═Q)— group, a —NR
6
NR
6a
— group or a —NR
6
C(R
4
)R
5
— group, each of R
4
and R
5
is a hydrogen atom, a C
1
-C
6
alkyl group, a halogen atom, a C
1
-C
6
alkoxy group or a C
1
-C
6
alkylthio group, each of R
6
and R
6a
is a hydrogen atom, a C
1
-C
6
alkyl group, a C
2
-C
6
alkenyl group or a C
2
-C
6
alkynyl group, here R
3
and R
6
may, together with the carbon atom to which they are bonded, form a 5- to 7-membered cyclic urea, Ar is a group represented by any one of the formulae Ar-1 to Ar-17:
(wherein X′ is a hydrogen atom, a halogen atom, a C
1
-C
6
alkyl group, a C
2
-C
6
alkenyl group, a C
2
-C
6
alkynyl group, a C
1
-C
6
alkoxy group, a C
1
-C
6
alkoxy C
1
-C
6
alkyl group, a NR
9
R
10
group, a CONR
9
R
10
group, a C
1
-C
4
haloalkoxy group, a C
2
-C
6
alkenyloxy group, a C
3
-C
6
cycloalkyloxy group, a C
2
-C
7
acyl group, a C
1
-C
6
alkoxycarbonyl group, a C
1
-C
6
alkylthio group, a C
1
-C
6
alkylsulfinyl group, a C
1
-C
6
alkylsufonyl group, a cyano group, a nitro group or a C
1
-C
4
haloalkyl group, n′ is an integer of from 1 to 3, m is an integer of from 0 to 3, when n′ is an integer of 2 or 3, the plurality of X′ may be the same or different, and two adjacent lower alkoxy groups may be bonded to each other to form a C
1
-C
3
alkylenedioxy group), R
7
is a hydrogen atom, a halogen ato

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