Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1995-12-28
1999-11-09
Morris, Patricia L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514 91, 548410, 548413, A01N 4390, C07D491107
Patent
active
059815671
DESCRIPTION:
BRIEF SUMMARY
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), (EP 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-arylpyrrolidine-dione derivatives (EP 456 063) and (EP 521 334).
There have now been found new substituted spirocyclic 1H-3-aryl-pyrrolidine-2,4-dione derivatives of the formula (I) ##STR2## 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, ##STR3## E represents a metal ion equivalent or an ammonium ion, L and M in each case represent oxygen or sulphur, 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, alkenyl, alkoxyalkyl, polyalkoxyalkyl or in each case optionally substituted phenyl or benzyl, 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, 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 structures (Ia) to (Ig) result: ##STR4## in which A, B, E, L, M, X, Y, Z, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.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) ##STR5## in which A, B, X, Y, Z and n have the abovementioned meaning, are obtained when N-acylamino acid esters of the formula (II) ##STR6## in which A, B, X, Y, Z and n have the abovementioned meaning and a diluent and in the presence of a base; or
(B) compounds of the formula (Ib) ##STR7## in which A, B, X, Y, Z, R.sup.1 and n have the abovementioned meaning, are obtained when compounds of the formula (Ia) ##STR8## in which A, B, X, Y, Z and n have the abovementioned meaning, ##STR9## in which R.sup.1 has the abovementioned meaning and presence of an acid-binding agent or presence of an acid-binding agent; or
(C) compounds of the form
REFERENCES:
patent: 5258527 (1993-11-01), Krauskopf et al.
patent: 5462913 (1995-10-01), Fischer et al.
Cram and Hammond, "Organic Chemistry", 2nd Ed (1964) NY: McGraw-Hill Book Co.
Bretschneider Thomas
Dollinger Markus
Erdelen Christoph
Fischer Reiner
Kruger Bernd-Wieland
Bayer Aktiengesellschaft
Morris Patricia L.
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