Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1996-05-13
1997-11-04
McKane, Joseph
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
504284, 504299, 514405, 514413, 514462, 544235, 548453, 549265, A01N 4356, A61K 31415, C07D23726
Patent
active
056839650
DESCRIPTION:
BRIEF SUMMARY
This is a filing under 35 U.S.C. .sctn. 371 of PCT/EP94/02042, filed Jun. 22, 1994.
The present invention relates to novel substituted aryl keto-enolic heterocycles, to a number of processes for their preparation and to their use as pesticides.
It is known that certain substituted .DELTA..sup.3 -dihydrofuran-2-one derivatives possess herbicidal properties (cf. DE-A 4 014 420). The synthesis of the tetronic acid derivatives (such as for example 3-(2-methyl-phenyl)-4-hydroxy-5-(4-fluorophenyl).DELTA..sup.3 -dihydrofuran-2-one) used as starting compounds is likewise described in DE-A 4 014 420. Compounds of similar structure, without the indication of insecticidal and/or acaricidal activity, are known from the publication Campbell et al., I. Chem. Soc., Perkin Trans. 1 1985, (8) 1567-76.
Pharmaceutical properties have been described previously for 3-acyl-pyrrolidine-2,4-diones (S. Suzuki et al. Chem. Pharm. Bull. 15 1120 (1967)). Furthermore, N-phenyl-pyrrolidine-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 discloses compounds of similar structure (3-aryl-pyrrolidine-2,4-diones) for which, however, no herbicidal, insecticidal or acaricidal action has become known. Known to have a herbicidal, insecticidal or acaricidal action are unsubstituted, bicyclic 3-aryl-pyrrolidine-2,4-dione derivatives (EP-A 355 599 and EP 415 211), substituted bicyclic 3-aryl-pyrrolidine-2,4-dione derivatives (EP 501 129) and substituted mono-cyclic 3-aryl-pyrrolidine-2,4-dione derivatives (EP-A 377 893, EP 442 077 and EP 497 127).
Polycyclic 3-aryl-pyrrolidine-2,4-dione derivatives (EP-A442 073), 1H-3-aryl-pyrrolidine-dione derivatives (EP 456 063 and EP 521 334) and substituted bicyclic 3-aryl-pyrrolidine-dione derivatives (EP 501 129) are also known.
Also known are tetronic acid derivatives having fungicidal, herbicidal, acaricidal and insecticidal properties (EP 528 156). 4-Arylpyrazolidine-dione derivatives having herbicidal, acaricidal and insecticidal properties are described in WO 92/16510 and EP 508 126.
Novel substituted aryl keto-enolic heterocycles have now been found of the formula (I) ##STR2## in which X represents alkyl, halogen or alkoxy, ##STR3## A and B can be identical or different and represent hydrogen, in each case optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, cycloalkyl which is optionally interrupted by at least one heteroatom, or aryl, aralkyl or hetaryl each of which is optionally substituted by halogen, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy or nitro, saturated or unsaturated ring which is optionally interrupted by at least one heteroatom and is optionally substituted, alkenyl, alkoxyalkyl, alkylthioalkyl, cycloalkyl which is optionally interrupted by at least one heteroatom, or aryl, aralkyl or hetaryl each of which is optionally substituted by halogen, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy or nitro, saturated or unsaturated monocyclic, bicyclic or tricyclic ring system which is optionally interrupted by at least one heteroatom and is optionally substituted, ##STR4## in which R.sup.1 represents hydrogen or alkyl, alkinyl, cycloalkyl, alkoxyalkyl, alkylthioalkyl, aryl or aralkyl, alkyl or phenyl, nitro, and
Depending on the substituents, the compounds of the formula (I) can be present as geometrical and/or optical isomers or isomer mixtures of varying compositions. Both the pure isomers and the isomer mixtures, the preparation and use thereof, and compositions comprising them are part of the claimed invention. However, for the sake of simplicity the text below refers always to compounds of the formula (I) although what is meant are both the pure compounds and, if appropriate, mixtures with varying proportions of isomeric compounds.
It has also been found that the novel compounds of the formula (I) have a very good activity as pesticides, preferably as arthropodicides, fungicides and herbicides.
It additionally been found that the no
REFERENCES:
patent: 4985063 (1991-01-01), Fischer et al.
patent: 5045560 (1991-09-01), Fischer et al.
patent: 5091537 (1992-02-01), Fischer et al.
patent: 5094681 (1992-03-01), Kramer et al.
patent: 5116836 (1992-05-01), Fischer et al.
patent: 5142065 (1992-08-01), Fischer et al.
patent: 5186737 (1993-02-01), Fischer et al.
patent: 5191089 (1993-03-01), Baasner et al.
patent: 5225434 (1993-07-01), Bertram et al.
patent: 5258527 (1993-11-01), Krauskopf et al.
patent: 5262383 (1993-11-01), Fischer et al.
patent: 5288874 (1994-02-01), Santel et al.
patent: 5304530 (1994-04-01), Cliff et al.
patent: 5332720 (1994-07-01), Kruger et al.
patent: 5474974 (1995-12-01), Kruger et al.
patent: 5504057 (1996-04-01), Fischer et al.
Bachmann Jurgen
Bretschneider Thomas
Dollinger Markus
Erdelen Christoph
Fischer Reiner
Bayer Aktiengesellschaft
McKane Joseph
Myers, Jr. Richard S.
LandOfFree
Substituted aryl keto-enolic heterocycles does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Substituted aryl keto-enolic heterocycles, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Substituted aryl keto-enolic heterocycles will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1832954