Nitroimino-nitromethylene—azole or-azine heterocyclic...

Details Nitroimino-nitromethylene—azole or-azine heterocyclic... Nitroimino-nitromethylene—azole or-azine heterocyclic...

1999-05-11

2001-10-02

Higel, Floyd D. (Department: 1626)

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

Organic compounds

Chalcogen in the nitrogen containing substituent

C504S129000, C504S130000, C504S131000, C504S136000, C504S138000, C504S139000, C504S140000, C544S333000, C544S367000, C546S269700, C546S271400, C546S274700, C548S134000, C548S202000, C548S247000

Reexamination Certificate

active

06297374

ABSTRACT:

The present invention relates to novel heterogyclic compounds, to processes for their preparation, to their use as insecticides.
It has already been disclosed that not only certain nitromethylene derivatives have insecticidal function, for instance, 1-benzyl-2-nitromethylene tetrahydropyrimidine (see DE-OS 2,514,402), but certain triazolidine derivatives have anti-tumor function against gastrointestinal tumor (see Japanese Laid-Open Patent Publication 196,877/1984).
Furthermore, 1-benzyl-2-nitroiminoimidazolidine has been described in Can. J. Chem., vol. 39, pages 1787-1796.
There have now been found novel heterocyclic compounds of the formula (I):
wherein
n represents 0 or 1,
R
1
, R
2
, R
5
and R
6
independently represent a hydrogen atom or an alkyl group, R
3
and R
4
independently represent a hydrogen atom, a hydroxy group or an alkyl group,
where n represents 1, then R
2
may form a single bond, together with R
5
,
X represents a sulfur atom, an oxygen atom,
or
wherein
R
7
represents a hydrogen atom, a halogen atom,
a hydroxy group, an alkoxy group,
a benzyloxy group, an alkyl group which may be substituted by at least one substituent selected from the class consisting of alkoxy groups, alkylthio groups, a cyano group, halogen atoms, dialkylamino groups and trialkylsilyl,
an alkenyl group which may be substituted by a halogen atom, an alkynyl group which may be substituted by a halogen atom, a phenyl group which may be substituted by an alkyl group and/or a halogen atom,
a benzyl group which may be substituted by at least one substituent selected from the class consisting of a methyl group, a methoxy group, halogen atoms, halomethyl groups, halomethoxy groups and a nitro group, a formyl group,
an alkenylcarbonyl group, an alkylcarbonyl group which may be substituted by at least one substituent selected from the class consisting of alkoxy groups, a phenoxy group, alkylthio groups, and halogen atoms, a benzoyl group which may be substituted by at least one substituent selected from the class consisting of halogen atoms, alkyl groups, halomethyl groups, alkoxy groups, haloalkoxy groups and a nitro group, a benzyl-carbonyl group which may be substituted by an alkyl group and/or a halogen atom, an alkoxycarbonyl group which may be substituted by a halogen atom, an alkylthiocarbonyl group,
a phenoxycarbonyl group which may be substituted by at least one substituent selected from the class consisting of methyl group, a methoxy group, halomethyl group, halomethoxy groups, halogen atoms and a nitro group, a phenylthiocarbonyl group which may be substituted by a halogen atom and/or an alkyl group,
a benzyloxycarbonyl group,
a monoalkyl- or dialkyl-aminocarbonyl group,
a phenylaminocarbonyl group which may be substituted by at least one substituent selected from the class consisting of alkyl groups, haloalkyl groups and halogen atoms, a benzoylaminocarbonyl group which may be substituted by an alkyl group and/or a halogen atom,
a phenylsulfonylaminocarbonyl group which may be substituted by an alkyl group and/or a halogen atom, a phenylthio group which may be substituted by an alkyl group and/or a halogen atom, an alkylsulfonyl group which may be substituted by a halogen atom, a phenylsulfonyl group which may be substituted by at least one substituent selected from the class consisting of alkyl groups, halogen atoms and a nitro group, an alkylcarbonylmethyl group,
a phenacyl group which may be substituted by a halogen atom and/or an alkyl group,
an organophosphono group, an organothionophosphono group,
—CH
2
—W or —CO—W,
 wherein
W represents a 5 to 6 membered heterocyclic group, containing at least one hetero atom selected from the class consisting of an oxygen atom, a sulfur atom and a nitrogen atom, which may be substituted by at least one substituent selected from the class consisting of halogen atoms, alkyl groups and haloalkyl groups,
R
8
represents a hydrogen atom, an alkyl group, an aryl group or a benzyl group,
Y represents a nitrogen atom or
wherein
R
9
represents a hydrogen atom, a halogen atom, a hydroxy group, an alkoxy group, a benzyloxy group, an alkyl group which may be substituted by at least one substituent selected from the class consisting of halogen atoms, a hydroxy group, alkoxy groups, alkylthio groups, a cyano group, mono- or dialkylamino groups, alkylcarbonyl groups, alkoxycarbonyl groups and phenoxycarbonyl groups,
an alkenyl group which may be substituted by a halogen atom, an alkynyl group, a phenyl group which may be substituted by an alkyl group and/or a halogen atom, an alkylcarbonyl group which may be substituted by a halogen atom, an alkenylcarbonyl group, a benzoyl group which may be substituted by at least one substituent select from the class consisting of halogen atoms, alkyl groups and alkoxy groups,
an alkoxycarbonyl group which may be substituted by a halogen atom,
an alkylthiocarbonyl group,
a phenoxycarbonyl group which may be substituted by at least one substituent selected from the class consisting of halogen atoms, alkyl groups, alkoxy groups and a nitro group,
a phenylthiocarbonyl group which may be substituted by an alkyl group and/or a halogen atom, a phenylthiocarbonyl group which may be substituted by an alkyl group and/or a halogen atom, a benzyloxycarbonyl group,
a benzoylaminocarbonyl group which may be substituted by an alkyl group and/or a halogen atom, a phenylsulfonylaminocarbonyl group which may be substituted by an alkyl group and/or a halogen atom, an alkylsulfonylaminocarbonyl group,
an alkylthio group,
an alkylsulfonyl group which may be substituted by a halogen atom,
a phenylthio group which may be substituted by an alkyl group and/or a halogen atom,
a phenylsulfonyl group which may be substituted by an alkyl group and/or a halogen atom, in addition, R
9
may form a bis-form of the formula (I), via a methylene group,
R represents a hydrogen atom or an alkyl group, and
Z represents a 5 to 6 membered heterocyclic group containing at least one hetero atom selected from the class consisting of an oxygen atom, a sulfur atom and a nitrogen atom, which may be substituted by at least one substituent selected from the class consisting of halogen atoms, alkyl groups, haloalkyl groups, a nitro group, a cyano group, alkoxy groups, alkylthio groups, alkylsulfinyl groups, alkylsulfonyl groups, alkenyl groups, haloalkoxy group, haloalkylthio groups, haloalkenyl groups, acylamino groups, haloacylamino groups, alkoxycarbonyl groups,
a thiocyanato group, alkynyl groups, an amino group, alkylamino groups, dialkylamino groups, a carboxy group, a hydroxy group, a mercapto group, cycloalkyl groups, an oxo group,
a thioxo group, haloalkenylthio groups, alkoxyalkyl groups, alkoxycarbonylamino groups,
a carbamoyl group, acyl groups, alkylaminocarbonyl groups, dialkylaminocarbonyl groups, a formyl group, aryl groups optionally substituted by a substituent selected from the class consisting of halogen atoms, alkyl groups, halogenoalkyl groups, alkoxy groups, a nitro group and a cyano group, aryloxy groups optionally substituted by the substituent as that shown for the above aryl groups, and
aralkyl groups optionally substituted by the same substituent as that shown for the aryl groups, provided that where R
1
, R
2
, R
3
, R
4
, R
5
and R
6
represent hydrogen atoms simultaneouly,
X represents
and Y represents
then Z must not stand for the pyridyl group.
In the case of compounds according to the formula (I) having the following formula (Ia):
wherein
n, R
1
, R
2
, R
3
, R
4
, R
5
, R
6
, R, R
9
and Z have the same meanings as stated above,
X
1
represents a sulfur atom, a oxygen atom or the following group
R
10
means, in the definition of R
7
, other groups than acyl groups including sulfonyl groups and phosphono groups,
the compounds of the formula (Ia) are obtained when
(a) the compounds of the formula (II)
wherein n, R
1
, R
2
, R
3
, R
4
, R
5
, R
6
, R, X
1
and Z have the same meanings as stated above,
are reacted with the compounds of the formula (III)
wherein R′ represents a lower alkyl or a benzyl group, or

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