Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2000-06-12
2002-01-22
Gerstl, Robert (Department: 1626)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C514S340000, C514S342000, C514S361000, C514S362000, C546S177000, C546S277100, C548S125000, C548S127000, C548S134000
Reexamination Certificate
active
06340697
ABSTRACT:
TECHNICAL FIELD
This invention relates to novel oxime derivatives and agricultural chemicals including the oxime derivatives as active ingredients and, particularly relates to control chemicals for plant diseases.
BACKGROUND ART
Regarding oxime derivatives which are effective as agricultural chemicals or pesticides, Japanese Patent Application, First Publication No. Hei 7-25224 by the present inventors discloses, for example, that 4, 5-substituted-1, 2, 3-thiadiazole derivatives are effective as control chemicals for plant diseases.
Although the above derivatives are effective as control chemicals, it is desired to develop new agricultural chemicals which are superior in effects in a lesser amount than the above thiadiazole derivatives.
DISCLOSURE OF INVENTION
The problems to be solved by the present invention are, therefore, to provide a new oxime derivative which is sufficiently effective to treat plant diseases in small amounts without causing damage or phytotoxicity to the plant and agricultural chemicals or pesticides containing the above mentioned oxime derivative as an active ingredients, particularly, as the control chemicals for plant diseases.
The inventors of the present invention have synthesized new oxime derivatives and have investigated bioactivities of these derivatives in order to solve the above problems. After a series of investigations, this invention was completed by discovering that oxime derivatives represented by general chemical formulas (1) and (2) are particularly effective, showing superior bioactivity against various bacteria causing plant diseases, and without showing any phytotoxicity.
The present invention provides the following oxime derivatives and agricultural chemicals containing said oxime derivatives as effective agents:
(1) an oxime derivative represented by the following general chemical formula (1),
wherein,
R
1
represents a hydrogen atom or a lower alkyl group; X represents a halogen atom, a nitro group, a hydroxyl group, a cyano group, a carboxyl group, an alkoxy-carbonyl group, a lower alkyl group which may be substituted with halogen atoms; a lower alkoxy group which may be substituted with halogen atoms; a lower alkylthio group which may be substituted with halogen atoms; a lower alkylsulfonyl group which may be substituted with a halogen atom; an aryl group which may be substituted with a halogen atom or a lower alkyl group; an aryloxy group which may be substituted with a halogen atom or a lower alkyl group; or an amino group which may be substituted with a lower alkyl group; and n represents an integer from 0 to 3; and
Het A represents a 6-membered aromatic nitrogen-containing ring which contains one or two nitrogen atoms or its benzo-condensation ring-type nitrogen containing aromatic ring which may be substituted with one or two substitutable groups selected from the group consisting of a halogen atom, a lower alkyl group, a lower alkylthio group, a lower alkylsulfonyl group, a lower alkoxy group, a trifluoromethyl group, and a cyano group; and
Het B represents oxime derivatives, each ring structure, expressed by the following formulas,
wherein,
Y represents a hydrogen atom, a halogen atom, or a lower alkyl group which may be substituted with a halogen atom;
(2) an oxime derivative expressed by the following general chemical formula (2);
[wherein,
R
1
,X, n, Het B, and Y are the same as those defined in the chemical formula (1), and Het C represents a 5-membered nitrogen containing aromatic ring or its benzo-condensation ring-type nitrogen containing aromatic ring which contains more than one nitrogen atom, or which may contain a sulfur atom or an oxygen atom, and which may be substituted with more than one substituting group, and the substitutable groups on a nitrogen atom of said 5-membered nitrogen containing aromatic ring are groups selected from the group consisting of a lower alkyl group, a lower alkyl-sulfonyl group, triphenylmethyl group, a lower alkoxymethyl group and a N, N-di-substituted sulfamoyl group substituted with lower alkyl groups, and the substitutable groups on a carbon atom of said 5 membered nitrogen containing aromatic ring are groups selected from the group consisting of a halogen atom, a cyano group, an alkyl group ranging from C
1
to C
6
which may be substituted with a halogen atom, and a cycloalkyl group ranging from C
3
to C
6
; and
an alkenyl group ranging from C
2
to C
6
, an alkinyl group ranging from C
2
to C
6
, an alkoxy group ranging from C
1
to C
5
which may be substituted with a halogen atom, a lower alkylthio group which may be substituted with a halogen atom, a lower alkylsulfonyl group which may be substituted with a halogen atom, a lower alkyl sulfinyl group which may be substituted with halogen atoms, an amino group which may be substituted with a lower alkyl group or a cycloalkyl group ranging from C
3
to C
6
or a triphenyl-methyl group; and
a lower alkoxy-carbonyl group, a carbamoyl group which may be substituted with lower alkyl groups, an aminomethyl group which may be substituted with lower alkyl groups, an acylaminomethyl group, N-alkoxycarbonyl-aminomethyl group, an alkyl thiomethyl group, aryl group which may be substituted with halogen atoms, and a heteroaryl group which may be substituted with halogen atoms, and
a group expressed by —N (R
2
) C (═O) R
3
(wherein, R
2
represents a hydrogen atom or a methyl group, and R represents a hydrogen atom, an alkyl group ranging from C
1
to C
10
which may be substituted with halogen atoms, a cycloalkyl group ranging from C
3
to C
8
, an alkenyl group ranging from C
2
to C
6
, an alkinyl atoms ranging from C
2
to C
4
, an aralkyl group, a lower alkyl group substituted with an amino group, an aralkyl group substituted with an amino group, a lower alkyl group substituted with an acylamino group, an aralkyl group substituted with an acylamino group, a lower alkyl group substituted with an alkoxy-carbonyl-amino group, an aralkyl group substituted with an alkoxy-carbonyl-amino group, an aryl group which may be substituted with halogen atoms, lower alkyl groups which may be substituted with halogen atoms, lower alkoxy groups, lower alkylthio groups, amino groups, nitro groups or cyano groups, a heteroaryl group, a lower alkoxy group, a cycloalkyloxy group ranging from C
3
to C
6
, a benzyloxy group and an aryloxy group)],
(3) an oxime derivative expressed by the chemical formula (1), wherein Het A is a pyridyl group which may be substituted with one halogen atom or a lower alkyl group;
(4) an oxime derivative expressed by the chemical formula (2), wherein the Het C is a thiazolyl group which is expressed by the following chemical formula,
[wherein,
R
4
represents a hydrogen atom, an amino group, an alkoxy group ranging from C
1
to C
5
which may be substituted with halogen atoms, a lower alkylthio group which may be substituted with halogen atoms, a lower alkylsulfonyl group which may be substituted with halogen atoms, a lower alkylsulfinyl group which may be substituted with halogen atoms; or
a —NHC (═O) R
3
group (wherein, R
3
represents a hydrogen atom, an alkyl group ranging from C
1
to C
10
which may be substituted with halogen atoms, a cycloalkyl group ranging from C
3
to C
8
, an alkenyl group ranging from C
2
to C
6
, an alkinyl group ranging from C
2
to C
4
, an aralkyl group, a lower alkyl group substituted with an amino group, an aralkyl group substituted with an amino group, a lower alkyl group substituted with an acylamino group, an aralkyl group substituted with an acyl-amino group,
a lower alkyl group substituted with an alkoxycarbonylamino group, an aralkyl group substituted with an alkoxycarbonylamino group; an aryl group which may be substituted with halogen atoms, lower alkyl groups which may be substituted with halogen atoms, lower alkoxy groups, lower alkylthio groups, amino groups, nitro groups, or cyano groups; a heteroaryl group, a lower alkoxy group, or a cycloalkyloxy group ranging from C
3
to C
6
, a benzyl oxy group, or a aryloxy gro
Asada Toru
Goto Takashi
Goto Tomoko
Iiyama Mika
Kobori Takeo
Armstrong Westerman Hattori McLeland & Naughton LLP
Dainippon Ink and Chemicals Inc.
Gerstl Robert
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