Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
1999-06-03
2002-11-12
Morris, Patricica L. (Department: 1625)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C544S070000
Reexamination Certificate
active
06479489
ABSTRACT:
The invention relates to new substituted spirocyclic 1H-3-aryl-pyrrolidine-2,4-dione derivatives, to a plurality of processes for their preparation, and to their use as pesticides and as herbicides.
3-Acyl-pyrrolidine-2,4-diones have already been described as having pharmaceutical properties (S. Suzuki et al. Chem. Pharm. Bull. 15 1120 (1967)). Furthermore, N-phenyl-pyrrolidine-2,4-diones were synthesized by R. Schmierer and H. Mildenberger (Liebigs Ann. Chem. 1985 1095). These compounds were not described as having a biological activity. There have also been described 5-vinyl-tetramic acids which have pharmaceutical properties (GB-A 22 66 888).
EP-A 0 262 399 discloses 3-aryl-pyrrolidine-2,4-diones, but nothing has been disclosed about them having a herbicidal, insecticidal or acaricidal action. A herbicidal, insecticidal or acaricidal action has been disclosed in the case of unsubstituted bicyclic 3-aryl-pyrrolidine-2,4-dione derivatives (EP-A 355 599) and (EP 415 211) and of substituted monocyclic 3-aryl-pyrrolidine-2,4-dione derivatives (EP-A 377 893), (EP 442 077), (FP 497 127) and substituted bicyclic 3-aryl-pyrrolidone derivatives (EP 501 129).
Other compounds which have been disclosed are polycyclic 3-arylpyrrolidine-2,4-dione derivatives (EP 442 073) and 1H-3-arylpyrrolidinedione derivatives (EP 456 063) and (EP 521 334).
There have now been found new substituted spirocylic 1H-3-aryl-pyrrolidine-2,4-dione derivatives of the formula (I)
in which
A and B together with the carbon atom to which they are bonded represent an unsubstituted or substituted 5-6 membered cycle which is interrupted by at least one hetero atom,
X represents alkyl, halogen or alkoxy,
Y represents hydrogen, alkyl, halogen, alkoxy or halogenoalkyl,
Z represents alkyl, halogen or alkoxy,
n represents a number 0, 1, 2 or 3,
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 sulphur,
R
1
represents alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl or cycloalkyl which can be interrupted by hetero atoms, each of these radicals optionally being substituted by halogen, or represents in each case optionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl,
R
2
represents in each case optionally substituted alkyl, cycloalkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl or in each case optionally substituted phenyl or benzyl,
R
3
, R
4
and R
5
independently of one another represent alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio, cycloalkylthio, each of which is 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 alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, each of which is optionally substituted by halogen, or represent optionally substituted phenyl or optionally substituted benzyl, or together with the N atom to which they are bonded represent a cycle which is optionally interrupted by oxygen or sulphur.
Taking into consideration the various meanings (a), (b), (c), (d), (e) and (f) of group G in the general formula (I), the following main struggles (Ia) to (Ig) result:
in which
A, S, E, L, M, Y, Z , R
1
, R
2
, R
3
, R
4
, R
5
, R
6
, R
7
and n
have the abovementioned meanings.
Due to one or more chiral centres, the compounds of the formula (Ia)-(Ig) are generally obtained in the form of a stereoisomer mixture. They can be used in the form of their diastereomer mixtures or as the pure diastereomers or enantiomers.
Furthermore, it has been found that the new substituted 1H-3-aryl-pyrrolidine-2,4-dione derivatives of the formula (I) are obtained by one of the processes described hereinbelow.
(A) 1H-3-Aryl-pyrrolidine-2,4-diones or their Enols of the Formula (Ia)
in which
A, B, Y, Z and n have the abovementioned meaning,
are obtained when
N-acylamino acid esters of the formula (II)
in which
A, B, X, Y, Z and n have the abovementioned meaning 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
(B) Compounds of the Formula (Ib)
in which
A, B, X, Y, Z, R
1
and n have the abovementioned meaning,
are obtained when compounds of the formula (Ia)
s in which
A, B, X Y, Z and n have the abovementioned meaning,
&agr;) are reacted with acid halides of the formula (III)
in which
R
1
has the abovementioned meaning and
Hal represents halogen, in particular chlorine and bromine,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid-binding agent
or
&bgr;) are reached with carboxylic anhydrides of the 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-1)
in which
A, B, X, Y, A R
2
and n have the abovementioned meaning,
and
M represents oxygen or sulphur
are obtained when compounds of the formula (Ia)
in which
A, B, X, Y, Z and n have the abovementioned meaning,
are reacted with chloroformic ester or chloroformic thiol ester of the formula (V)
R
2
—M—CO—Cl (V)
in which
R
2
and M have the abovementioned meaning,
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-2)
in which
A, B, R
2
, Y, Z and n have the abovementioned meaning
and
M represents oxygen or sulphur,
are obtained when compounds of the formula (Ia)
in which
A, B, X, Y, Z and n have the abovementioned meaning,
&agr;) are reacted with chloromonothioformic esters or chlorodiothioformic esters of the formula (VI)
in which
M and R
2
have the abovementioned meaning,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid-binding agent,
or
are reacted with carbon disulphide and subsequently 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,
if appropriate in the presence of a diluent and if appropriate in the presence of an auxiliary base;
or
(E) compounds of the formula (Id)
in which
A, B, X, Y, R
3
and n have the abovementioned meaning,
are obtained when compounds of the formula (Ia)
in which
A, B, X, Y, Z and n have the abovementioned meaning,
are reacted with sulphonyl chlorides of the formula (VIII)
R
3
—SO
2
—Cl (VII)
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) 3-aryl-pyrrolidine-2,4-diones of the formula (Ie)
in which
A, B, L, X, Y, Z, R
4
, R
5
and n have the abovementioned meaning,
are obtained when
1-H-3-aryl-pyrrolidine-2,4-diones of the formula (Ia) or their enols
in which
A, B, X, Y, Z and n have the abovementioned meaning,
are reacted with phosphorus compounds of the formula (IX)
in which
L, R
4
and R
5
have the abovementioned meaning
and
Hal represents halogen, in particular chlorine and bromine,
if appropriate in the presence of a diluent and if appropriate in the presence of an acid-binding agent;
or
(G) compounds of the formula (If)
in which
A, B, X, Y, Z and n have the abovementioned meaning,
and
E represents a metal ion equivalent or an ammonium ion,
are obtained when compounds of the formula (Ia)
in which
A, B, X, Y, Z and n have the abovementioned meaning,
are reacted with metal compounds or amines of the formulae (X) and (XI)
in which
Me represents mono- or divalent metal ions,
t represents the number 1 or 2,
R
10
, R
11
and R
12
independently of one another represent hydrogen or alkyl and
R
13
represents hydrogen, hydroxyl or C
1
-C
4
-alkoxy,
if appropriate in the presence of a diluent.
H) Furthermore, it has been found tat compounds of the formula (I-g)
in which
Bretschneider Thomas
Dollinger Markus
Erdelen Christoph
Fischer Reiner
Krüger Bernd-Wieland
Bayer Aktiengesellschaft
Morris Patricica L.
Norris MCLaughlin & Marcus
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