Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1996-09-27
1998-11-03
McKane, Joseph K.
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
504283, 514 91, 514409, 514425, 548408, 548413, 548544, A01N 4336, A61K 3140, C07D20708
Patent
active
058308261
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP95/01100 filed Mar. 23, 1995.
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) ##STR2## 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, a saturated or unsaturated, unsubstituted or substituted ring which is optionally interrupted by at least one heteroatom, ##STR3## E represents a metal ion equivalent or an ammonium ion, L represents oxygen or sulfur, 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, alkenyl, alkoxyalkyl or polyalkoxyalkyl, or represents in each case optionally substituted cycloalkyl, phenyl or benzyl, case optionally halogeno-substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio or cycloalkylthio or represent in each case optionally substituted phenyl, phenoxy or phenylthio, 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, alkoxy if X represents alkyl. (g) of the group G results in the following principal structures (Ia) to (Ig): ##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 and R.sup.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) ##STR5## in which A, B, X, Y and Z have the meaning given above, are obtained if ##STR6## in which A, B, X, Y and Z have the meaning given above, and and in the presence of a base;
(B) compounds of the formula
Bretschneider Thomas
Dollinger Markus
Erdelen Christoph
Fischer Reiner
Kruger Bernd-Wieland
Bayer Aktiengesellschaft
McKane Joseph K.
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