1-H-3-aryl-pyrrolidine-2, 4-dione derivatives as...

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...

Reexamination Certificate

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C514S091000, C548S413000, C548S544000

Reexamination Certificate

active

06472419

ABSTRACT:

The invention relates to new 1-H-3-aryl-pyrrolidine-2,4-dione derivatives, to a plurality of processes for their preparation, and to their use as pesticides, in particular as insecticides and acaricides.
3-Acyl-pyrrolidine-2,4-diones have previously been described as having pharmaceutical properties (S. Suzuki et al. Chem. Pharm. Bull. 15 1120 (1967)). Moreover, N-phenylpyrrolidine-2,4-diones have been synthesized by R. Schmierer and H. Mildenberger (Liebigs Ann. Chem. 1985 1095). A biological activity of these compounds has not been described.
EP-A 0 262 399 and GB-A 2 266 888 disclose compounds of a similar structure (3-aryl-pyrrolidine-2,4-diones), but nothing has been disclosed about them having a herbicidal, insecticidal or acaricidal activity. Known, and having a herbicidal, insecticidal or acaricidal activity, are unsubstituted bicyclic 3-aryl-pyrrolidine-2,4-dione derivatives (EP-A 355 599 and EP 415 211) and substituted monocyclic 3-aryl-pyrrolidine-2,4-dione derivatives (EP-A 377 893 and EP 442 077).
Substances which are furthermore known are polycyclic 3-aryl-pyrrolidine-2,4-dione derivatives (EP 442 073) and 1-H-3-aryl-pyrrolidine-dione derivatives (EP 456 063 and EP 521 334).
New substituted 1-H-3-aryl-pyrrolidine-2,4-dione derivatives have now been found, of the formula (I)
in which
A represents hydrogen, or represents alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl or alkylthioalkyl, in each case optionally substituted by halogen, or represents cycloalkyl which is optionally interrupted by at least one hetero atom, or represents aryl, arylalkyl or hetaryl, in each case optionally substituted by halogen, alkyl, halogenoalkyl, alkoxy or nitro,
B represents hydrogen, alkyl or alkoxyalkyl, or
A and B together with the carbon atom to which they are bonded represent a saturated or unsaturated, unsubstituted or substituted cycle which is optionally interrupted by at least one hetero atom,
X represents halogen or alkoxy,
Y represents hydrogen, halogen or alkoxy,
Z represents hydrogen, halogen or alkoxy,
G represents hydrogen (a) or the groups
E represents a metal ion equivalent or an ammonium ion,
L and M in each case represent oxygen or sulfur,
R
1
represents alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl or cycloalkyl which can be interrupted by hetero atoms, in each case optionally substituted by halogen, or represents optionally substituted phenyl or in each case optionally substituted phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl,
R
2
represents alkyl, alkenyl, alkoxyalkyl or polyalkoxyalkyl, in each case optionally substituted by halogen, or represents in each case optionally substituted cycloalkyl, phenyl or benzyl,
R
3
, R
4
and R
5
independently of one another represent alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio or cycloalkylthio, in each case optionally substituted by halogen, or represent in each case optionally substituted phenyl, phenoxy or phenylthio,
R
6
and R
7
independently of one another represent hydrogen, or represent alkyl, cycloalkyl, alkenyl, alkoxy or alkoxyalkyl, in each case optionally substituted by halogen, or represent optionally substituted phenyl, or represent optionally substituted benzyl, or together with the N atom to which they are bonded represent a cycle which is optionally interrupted by oxygen or sulfur, with the proviso that X and Y or X and Z do not simultaneously represent halogen.
Taking into account the various meanings (a), (b), (c), (d), (e) (f) and (g) of group G of the general formula (I), the following main structures (Ia) to (Ig) result:
in which
A, B, E, L, M, X, Y, Z, R
1
, R
2
, R
3
, R
4
, R
5
, R
6
and R
7
have the abovementioned meanings.
Because of one or more chiral centers, the compounds of the formulae (Ia)-(Ig) are generally obtained in the form of a mixture of stereoisomers which, if appropriate, can be separated in the customary manner. They can be used in the form of their diastereomer mixtures as well as in the form of the pure diastereomers or enantiomers. For simplicity's sake, the following text will always mention compounds of the formulae (Ia) to (Ig), even though this is to be understood as meaning the pure compounds as well as the mixtures comprising various proportions of isomeric, enantiomeric and stereomeric compounds.
Furthermore, it has been found that the new substituted 1-H-3-aryl-pyrrolidine-2,4-dione derivatives of the formula (I) are obtained by one of the processes described below:
(A) 1-H-3-aryl-pyrrolidine-2,4-diones or their enols of the formula (Ia)
 in which
A, B, X, Y and Z have the abovementioned meanings, are obtained when
&agr;) N-acylamino acid esters of the formula (II)
 in which
A, B, X, Y and Z have the abovementioned meanings, and
R
8
represents alkyl are subjected to an intramolecular condensation reaction in the presence of a diluent and in the presence of a base; or
&bgr;) 1-H-3-aryl-pyrrolidine-2,4-diones or their enols of the formula (Ia-a)
 in which
A, B, X and Z have the abovementioned meanings, and
Y
1
represents —OR
8
, where
R
8
represents alkyl, are obtained when N-acylamino acid esters of the formula (IIa)
 in which
A, B, X and Z have the abovementioned meanings,
Y
2
represents fluorine and
R
8
represents alkyl, preferably C
1
-C
8
-alkyl, are subjected to an intramolecular condensation reaction in the presence of a diluent and in the presence of a base; or
(B) compounds of the formula (Ib)
 in which
A, B, X, Y, Z and R
1
have the abovementioned meanings, are obtained when compounds of the formula (Ia),
 in which
A, B, X, Y and Z have the abovementioned meanings, are reacted
&agr;) with acid halides of the general formula (III)
 in which
R
1
has the abovementioned meaning and
Hal represents halogen, in particular chlorine or bromine, if appropriate in the presence of a diluent and if appropriate in the presence of an acid-binding agent, or
&bgr;) with carboxylic anhydrides of the general formula (IV)
R
1
—CO—O—CO—R
1
  (IV)
 in which
R
1
has the abovementioned meaning, if appropriate in the presence of a diluent and if appropriate in the presence of an acid-binding agent; or
(C) compounds of the formula (Ic-a)
 in which
A, B, X, Y, Z and R
2
have the abovementioned meanings, and
M represents oxygen or sulfur are obtained when compounds of the formula (Ia)
 in which
A, B, X, Y and Z have the abovementioned meanings, are reacted with chloroformic esters or chloroformic thioesters of the general formula (V)
R
2
—M—CO—Cl  (V)
 in which
R
2
and M have the abovementioned meanings, if appropriate in the presence of a diluent and if appropriate in the presence of an acid-binding agent; or
(D) compounds of the formula (Ic-b)
 in which
A, B, R
2
, X, Y and Z have the abovementioned meanings and
M represents oxygen or sulfur are obtained when compounds of the formula (Ia)
 in which
A, B, X, Y and Z have the abovementioned meanings are reacted
&agr;) with chloromonothioformic esters or chlorodithioformic esters of the general formula (VI)
 in which
M and R
2
have the abovementioned meanings, if appropriate in the presence of a diluent and if appropriate in the presence of an acid-binding agent, or
&bgr;) with carbon disulfide and then with alkyl halides of the general formula (VII)
R
2
—Hal  (VII)
 in which
R
2
has the abovementioned meaning and
Hal represents chlorine, bromine or iodine; or
(E) compounds of the formula (Id)
 in which
A, B, X, Y, Z and R
3
have the abovementioned meanings are obtained when compounds of the formula (Ia)
 in which
A, B, X, Y and Z have the abovementioned meanings are reacted with sulfonyl chlorides of the general formula (VIII)
R
3
—SO
2
—Cl  (VIII)
 in which
R
3
has the abovementioned meaning, if appropriate in the presence of a diluent and if appropriate in the presence of an acid-binding agent, or
(F) 1-H-3-aryl-pyrrolidine-2,4-diones of the formula (Ie)
 in which
A, B, L, X, Y, Z, R
4
and R
5
have the abovementioned mean

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