Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1996-09-18
1999-08-31
Morris, Patricia L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
549 62, 549 65, 549 66, A01N 4310, C07D33332
Patent
active
059454440
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to novel 3-aryl-4-hydroxy-.DELTA..sup.3 -dihydrothiophenone derivatives, to processes for their preparation and to their use as agents for controlling pests.
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-(3-methylphenyl)-4-hydroxy-5-(4-fluorophenyl-.DELTA..sup.3 -dihydrofuran-2-one) used as starting compounds is also described in DE-A 4 014 420. The publication Campbell et al. J. Chem. Soc., Perkin Trans. 1 1985, (8) 1567-8 also discloses similarly structured compounds without indicating any insecticidal and/or acaridical activity. In addition to this, EP 528 156 discloses 3-aryl-.DELTA..sup.3 -dihydrofuranone derivatives having herbicidal, acaridical and insecticidal properties; however, the effects described in this publication are not always adequate.
Novel 3-aryl-4-hydroxy-.DELTA..sup.3 -dihydrothiophenone derivatives of the formula (I) ##STR2## have now been found in which X represents alkyl, halogen, alkoxy or halogenoalkyl, with the phenyl radical to which they are bonded, form the naphthalene radical of the formula ##STR3## in which Y has the meaning given above, A and B can be identical or different and represent alkyl, alkenyl, alkinyl, alkoxyalkyl, polyalkoxyalkyl or alkylthioalkyl which are in each case optionally substituted identically or differently once or more than once by halogen, cycloalkyl which is optionally substituted and is optionally interrupted by at least one heteroatom, or aryl, arylkyl or hetaryl which are in each case optionally substituted identically or differently once or more than once by halogen, alkyl, halogenoalkyl, alkoxy, halogenoalkoxy or nitro, saturated or unsaturated ring which is optionally interrupted by at least one heteroatom and which is optionally substituted, or in which a ring in which two substituents, together with the carbon atoms to which they are bonded, represent a saturated or unsaturated ring which is optionally substituted identically or differently once or more than once by alkyl, alkoxy or halogen and which can be interrupted by oxygen or sulfur, ##STR4## E.sup..sym. represents a metal ion equivalent or an ammonium ion, L represents oxygen or sulfur, polyalkoxyalkyl which are in each case optionally substituted identically or differently once or more than once by halogen, or cycloalkyl which is optonally substituted by halogen or alkyl and can be interrupted by at least one heteroatom, or represents in each case optionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl, and in each case optionally substituted identically or differently once or more than once by halogen, or in each case optionally substituted cycloalkyl, phenyl or benzyl. alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio, alkinylthio or cycloalkylthio which are in each case optionally substituted identically or differently once or more than once by halogen or represent in each case optionally substituted phenyl, benzyl, phenoxy or phenylthio, alkyl, alkenyl, alkoxy or alkoxyalkyl which are in each case optionally substituted identically or differently once or more than once by halogen, represent in each case optionally substituted phenyl, or benzyl, optionally interrupted by oxygen or sulfur.
When the different meanings (a), (b), (c), (d), (e), (f) and (g) of the Group G are included, the following principle structures (Ia) to (Ig) ensue: ##STR5## where 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 possess the abovementioned meanings.
In general, due to the presence of one or more centers of chirality, the compounds of the formulae (Ia)-(Ig) result as stereoisomeric mixtures which can, where appropriate, be resolved in a customary manner. The compounds can be used both in the form of their diastereomeric mixtures and as pure diastereomers or enantiomers. For the sake of simplicity, reference will always be made be
REFERENCES:
patent: 5262383 (1993-11-01), Fischer et al.
J.Chem.Soc., Chemical Communications, No. 16, 1987, Letchworth GB, pp. 1228-1230, Chambers et al. `An Asymmetric Synthesis . . . Rearrangement.`
J.of Antibiotics, vol. 36, No. 11, 1983, pp. 1589-1591, Tsuzuki et al. `Biological Activities of thiotetromycin Analogs`.
Bretschneider Thomas
Dumas Jacques
Erdelen Christoph
Fischer Reiner
Wachendorff-Neumann Ulrike
Bayer Aktiengesellschaft
Morris Patricia L.
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