Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Reexamination Certificate
1998-07-31
2001-01-09
Powers, Fiona T. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
Reexamination Certificate
active
06172255
ABSTRACT:
The invention relates to novel 1H-3-aryl-pyrrolidine-2,4-dione derivatives, to a number of processes for their preparation and to their use as pesticides, especially as insecticides and acaricides.
Pharmaceutical properties of 3-acyl-pyrrolidine-2,4-diones have been described before (S. Suzuki et al. Chem. Pharm. Bull. 15 1120 (1967)). In addition, N-phenylpyrrolidine-2,4-diones have been synthesized by R. Schmierer and H. Mildenberger (Liebigs Ann. Chem. 1985 1095). No biological activity of these compounds has been described.
EP-A 0 262 399 and GB-A 2 266 888 disclose compounds of similar structure (3-aryl-pyrrolidine-2,4-diones) for which, however, no herbicidal, insecticidal or acaricidal action has been disclosed. Compounds which are known to have herbicidal, insecticidal or acaricidal action 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).
Polycyclic 3-aryl-pyrrolidine-2,4-dione derivatives (EP 442 073) and 1H-3-aryl-pyrrolidine-dione derivatives (EP 456 063 and EP 521 334) are also known.
Novel substituted 1H-3-aryl-pyrrolidine-2,4-dione derivatives have now been found of the formula (I)
in which
A represents hydrogen, in each case optionally halogeno-substituted alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl or alkylthioalkyl, cycloalkyl which is optionally interrupted by at least one heteroatom and optionally substituted, or represents in each case optionally halogen-, alkyl-, halogenoalkyl-, alkoxy- or nitro-substituted aryl, arylalkyl or hetaryl,
B represents alkyl or alkoxyalkyl, or
A and B together with the carbon atom to which they are attached represent a saturated or unsaturated, unsubstituted or substituted ring which is optionally interrupted by at least one heteroatom,
X represents alkyl or alkoxy,
Y represents hydrogen, alkyl or alkoxy,
Z represents hydrogen, alkyl or alkoxy,
G represents hydrogen (a) or represents the groups
E represents a metal ion equivalent or an ammonium ion,
L represents oxygen or sulfur,
M represents oxygen or sulfur,
R
1
represents in each case optionally halogeno-substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl or polyalkoxyalkyl, or optionally halogen- or alkyl-substituted cycloalkyl which may be interrupted by at least one heteroatom, or represents in each case optionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl,
R
2
represents in each case optionally halogeno-substituted alkyl, alkenyl, alkoxyalkyl or polyalkoxyalkyl, or represents in each case optionally substituted cycloalkyl, phenyl or benzyl,
R
3
, R
4
and R
5
independently of one another represent in each case optionally halogeno-substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio or cycloalkylthio or represent in each case optionally substituted phenyl, phenoxy or phenylthio,
R
6
and R
7
independently of one another represent hydrogen, represent in each case optionally halogeno-substituted alkyl, cycloalkyl, alkenyl, alkoxy or alkoxyalkyl, represent optionally substituted phenyl, represent optionally substituted benzyl, or together with N atom to which they are attached represent a ring which is optionally interrupted by oxygen or sulfur,
with the proviso that at least one of the substituents Y and Z represents alkoxy if X represents alkyl.
Taking into account the various meanings (a), (b), (c), (d), (e), (f) and (g) of the group G results in the following principal structures (Ia) to (Ig):
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
possess the meanings given above.
Because of one or more centres of chirality, the compounds of the formulae (Ia)-(Ig) are generally obtained as a mixture of stereoisomers, which can be separated if desired in a conventional manner. They may be used both in the form of their diastereomer mixtures and as pure diastereomers or enantiomers. For simplicity, the text below always uses the term compounds of the formula (Ia) to (Ig) although this refers not only to the pure compounds but also to the mixtures with different proportions of isomeric, enantiomeric and stereomeric compounds.
It has also been found that novel substituted 1H-3-aryl-pyrrolidine-2,4-dione derivatives of the formula (I) are obtained by one of the processes described below.
(A) 1H-3-Aryl-pyrrolidine-2,4-diones and/or their enols, of the formula (Ia)
in which
A, B, X, Y and Z have the meaning given above, are obtained if
N-acylamino acid esters of the formula (II)
in which
A, B, X, Y and Z have the meaning given above,
and
R
8
represents alkyl, especially C
1
-C
6
-alkyl
are subjected to intramolecular condensation 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 meaning given above,
are obtained if compounds of the formula (Ia)
in which
A, B, X, Y and Z have the meaning given above,
&agr;) are reacted with acid halides of the formula (III)
in which
R
1
has the meaning given above and
Hal represents halogen, especially chlorine or bromine,
optionally in the presence of a diluent and optionally in the presence of an acid-binding agent,
or
&bgr;) are reacted with carboxylic anhydrides of the formula (IV)
R
1
—CO—O—CO—R
1
(IV)
in which
R
1
has the meaning given above,
optionally in the presence of a diluent and optionally 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 meaning given above,
and
M represents oxygen or sulfur
are obtained if compounds of the formula (Ia)
in which
A, B, X, Y and Z have the meaning given above
are reacted with chloroformic esters or chloroformic thioesters of the formula (V)
R
2
—M—CO—Cl (V)
in which
R
2
and M have the meaning given above,
optionally in the presence of a diluent and optionally 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 meaning given above
and
M represents oxygen or sulfur
are obtained if compounds of the formula (Ia)
in which
A, B, X, Y and Z have the meaning given above,
&agr;) are reacted with chloromonothioformic esters or chlorodithioformic esters of the formula (VI)
in which
M and R
2
have the meaning given above
optionally in the presence of a diluent and optionally in the presence of an acid-binding agent,
or
&bgr;) are reacted with carbon disulfide and then with alkyl halides of the formula (VII)
R
2
—Hal (VII)
in which
R
2
has the meaning given above
and
Hal represents chlorine, bromine or iodine
optionally in the presence of a diluent and optionally in the presence of a base;
or
(E) compounds of the formula (Id)
in which
A, B, X, Y, Z and R
3
have the meaning given above
are obtained if compounds of the formula (Ia)
in which
A, B, X, Y and Z have the meaning given above
are reacted with sulfonyl chlorides of the formula (VIII)
R
3
—SO
2
—Cl (VIII)
in which
R
3
has the meaning given above
optionally in the presence of a diluent and optionally 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
and Rs have the meaning given above
are obtained if
1H-3-aryl-pyrrolidine-2,4-diones of the formula (Ia) and/or their enols
in which
A, B, X, Y and Z have the meaning given above
are reacted with phosphorus compounds of the formula (IX)
in which
L, R
4
and R
5
have the meaning given above
and
Hal represents halogen, especially chlorine or bromine,
optionally in the presence of a diluent and optionally in the presence of an acid-binding agent;
or
(G) compounds of the formula (If)
in which
A, B, X, Y and Z have the meaning given above
and
E represents a metal ion equivalent or an ammonium ion
are obtained if compounds of the formula (ia)
in which
A, B, X, Y and Z have the meaning given above
are reacted with metal hydroxides, metal alkoxides or amines of the formulae (X) and (XI)
in which
Me represen
Bretschneider Thomas
Dollinger Markus
Erdelen Christoph
Fischer Reiner
Kr{umlaut over (u)}ger Bernd-Wieland
Bayer Aktiengesellschaft
Norris McLaughlin & Marcus P.A.
Powers Fiona T.
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