Pyrazolinone derivatives

Details Pyrazolinone derivatives Pyrazolinone derivatives

2000-10-23

2001-09-25

Ramsuer, Robert W. (Department: 1626)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

C548S368700

Reexamination Certificate

active

06294567

ABSTRACT:

TECHNICAL FIELD
The present invention relates to the pyrazolinone derivatives, their uses and intermediate products.
BACKGROUND ART
The present invention aims at providing the compounds having an excellent plant disease controlling agent.
DETAILED DESCRIPTION OF THE INVENTION
As a result of extensive studies on the subject matter, the present inventors found that the pyrazolinone derivatives represented by the following formula [1] have an excellent controlling effect against plant diseases, and attained the present invention on the basis of this finding.
The present invention provides the pyrazolinone derivatives (hereinafter referred to as the present compounds) represented by the formula [I]:
[wherein R
1
, R
2
, R
3
, R
4
and R
5
may be identical or different and represent independently an hydrogen atom, a halogen atom, an alkyl group, a haloalkyl group, an alkoxy group, an alkoxyalkyl group, an alkoxyalkoxy group, a haloalkoxy group, an alkylthio group, a haloalkylthio group, a cyano group, a nitro group, an optionally substituted phenyl group or an optionally substituted phenoxyl group, or
adjacent two of R
1
, R
2
, R
3
, R
4
and R
5
are combined at the ends to represent a group of the formula CH═CH—CH═CH, a methylenedioxy group which may be substituted with a halogen atom, or an alkylene group which may contain one oxygen atom and may be substituted with an alkyl group;
R
6
represents an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted phenyl group, or an optionally substituted alicyclic hydrocarbon group;
X represents an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted phenyl group, an optionally substituted group, an optionally substituted alkenyloxy group, an optionally substituted alkynyloxy group, an optionally substituted phenoxyl group, an optionally substituted alkylthio group, an optionally substituted alkenylthio group, an optionally substituted alkynylthio group, an optionally substituted phenylthio group, or an optionally substituted alicyclic hydrocarbon group; and
Y represents an oxygen atom or a sulfur atom] and the plant disease controlling agents containing the present compound as an active ingredient.
The present invention further provides the pyrazolinone compounds represented by the following formula [II] which are useful as the intermediates for the preparation of the present compounds (these pyrazolinone compounds being hereinafter referred to as intermediates A):
[wherein R
11
, R
21
, R
31
, R
41
and R
51
may be identical or different and represent independently a hydrogen atom, a halogen atom, an alkyl group, a haloalkyl group, an alkoxy group, an alkoxyalkyl group, an alkoxyalkoxy group, a haloalkoxy group, an alkylthio group, a haloalkylthio group, a cyano group, a nitro group, an optionally substituted phenyl group or an optionally substituted phenoxyl group; or
adjacent two of R
11
, R
21
, R
31
, R
41
and R
51
are combined at the ends to represent a group of the formula CH═CH—CH═CH, a methylenedioxy group which may be substituted with a halogen atom, or an alkylene group which may contain one oxygen atom and may be substituted with an alkyl group; and
R
61
represents an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted phenyl group or an optionally substituted alicyclic hydrocarbon group]
and the pyrazolinone compounds represented by the formula [III] which are also useful as the intermediates for the preparation of the present compounds (these pyrazolinone compounds being hereinafter referred to as intermediates B):
[wherein R
12
, R
22
, R
32
, R
42
and R
52
may be identical or different and represent independently a hydrogen atom, a halogen atom, an alkyl group, a haloalkyl group, an alkoxy group, an alkoxyalkyl group, an alkoxyalkoxy group, a haloalkoxy group, an alkylthio group, a haloalkylthio group, a cyano group, a nitro group, an optionally substituted phenyl group or an optionally substituted phenoxyl group, or
adjacent two of R
12
, R
22
, R
32
, R
42
and R
52
are combined at the ends and represent a group of the formula CH═CH—CH═CH, a methylenedioxy group which may be substituted with a halogen atom, or an alkylene group which may contain one oxygen atom and may be substituted with an alkyl group;
X
1
represents an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted phenyl group, an optionally substituted alkoxy group, an optionally substituted alkenyloxy group, an optionally substituted alkynyloxy group, an optionally substituted phenoxyl group, an optionally substituted alkylthio group, an optionally substituted alkenylthio group, an optionally substituted alkynylthio group, an optionally substituted phenylthio group, or an optionally substituted alicyclic hydrocarbon group; and
Y
1
represents an oxygen atom or a sulfur atom].
MODES FOR CARRYING OUT THE INVENTION
In the present invention, the halogen atoms represented by R
1
, R
2
, R
3
, R
4
, R
5
, R
11
, R
21
, R
31
, R
41
, R
51
, R
12
, R
22
, R
32
, R
42
and R
52
in the formulae [I] to [III] include fluorine, chlorine, bromine and iodine.
The alkyl groups include C1-C5 alkyl groups such as methyl, ethyl, n-propyl, isopropyl, tert-butyl and n-pentyl.
The haloalkyl groups include C1-C5 haloalkyl groups such as trifluoromethyl, tetrafluoroethyl and heptafluoropropyl.
The alkoxy groups include C1-C5 alkoxy groups such as methoxy, ethoxy, normal propyloxy, isopropyloxy, n-butoxy and n-pentyloxy.
The alkoxyalkyl groups include C1-C3 alkoxy C1-C3 alkyl groups such as methoxymethyl, methoxyethyl, methoxypropyl, ethoxymethyl, ethoxyethyl and ethoxypropyl.
The alkoxyalkoxy groups include C1-C3 alkoxy C1-C3 alkoxy groups such as methoxymethoxy, methoxyethoxy, methoxypropoxy, ethoxymethoxy, ethoxyethoxy and ethoxypropoxy.
The haloalkoxy groups include C1-C5 haloalkoxy groups such as trifluoromethoxy, difluoromethoxy and tetrafluoroethoxy.
The alkylthio groups include C1-C5 alkylthio groups such as methylthio, ethylthio, n-propylthio, n-butylthio and n-pentylthio.
The haloalkylthio groups include C1-C5 haloalkylthio groups such as trifluoromethylthio.
The optionally substituted phenyl and phenoxyl groups include those which may be substituted with at least one group selected from halogen atoms, C1-C5 alkyl groups, C1-C5 alkoxy groups, C1-C5 alkylthio groups, C1-C5 haloalkyl groups, C1-C5 haloalkoxy groups, C1-C5 haloalkylthio groups and cyano groups.
Examples of the above-mentioned substituents are shown below:
Halogen atoms: fluorine, chlorine, bromine and iodine;
C1-C5 alkyl groups: methyl, ethyl, n-propyl, isopropyl, n-butyl and n-pentyl;
C1-C5 alkoxy groups: methoxy and ethoxy;
C1-C5 alkylthio groups: methylthio and ethylthio;
C1-C5 haloalkyl groups, preferably C1-C2 haloalkyl groups: trifluoromethyl;
C1-C5 haloalkoxy groups, preferably C1-C2 haloalkoxy groups: trifluoromethoxy and difluoromethoxy;
C1-C5 haloalkylthio groups, preferably C1-C2 haloalkylthio groups: trifluoromethylthio; and
Cyano groups.
Referring to the above R's, adjacent two of R
1
to R
5
, R
11
to R
51
, and R
12
to R
53
may be combined at the ends to form a methylenedioxy group which may be substituted with a halogen atom, such as difluoromethylenedioxy, or an alkylene group (such as C1-C6 alkylene group) which may contain an oxygen atom and may be substituted with an alkyl group (e.g. C1-C4 alkyl group), such as trimethylene, tetramethylene, a group of the formula OCH
2
CH
2
or a group of the formula OCH
2
CH(CH
3
).
In the present compounds in view of the controlling effect against plant diseases, it is desirable that 1 to 3 substituents selected from R
1
to R
5
is a halogen atom (especi

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