Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1997-09-29
2000-11-21
Raymond, Richard L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514361, 514529, 514530, 514531, 514538, 514622, 514676, 514683, 514684, 544311, 548130, 560 35, 560 60, 560128, 564163, 564164, 564165, 564167, 564256, 568329, 568330, 568375, 568377, 568379, A01N 3750, A01N 4354, C07C25148, C07D23952
Patent
active
061503746
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP96/01309, filed Mar. 25, 1996.
The invention relates to novel substituted cycloalkenes, to a plurality of processes for their preparation, and to novel intermediates and a plurality of processes for their preparation.
Certain substituted cycloalkenes are known to have fungicidal properties [cf. for example EP-A 421102].
However, in many cases the activity of these compounds is unsatisfactory.
This invention, accordingly, provides the novel substituted cycloalkenes of the general formula (I) ##STR2## in which E represents methylidene or nitrogen, respectively optionally halogen-, hydroxyl-, alkyl-, halogenoalkyl- or cycloalkyl-substituted alkanediyl or alkynediyl or one of the groupings below --Q--CQ--, --CQ--Q--, --CH.sub.2 --Q--, --Q--CH.sub.2 --, --CQ--Q--CH.sub.2 --, --CH.sub.2 --Q--CQ--, --Q--CQ--CH.sub.2 --, --Q--CQ--Q--CH.sub.2 --, --N.dbd.N--, --S(O).sub.n --, --CH.sub.2 --S(O).sub.n --, --CQ--, --S(O).sub.n --CH.sub.2 --, --C(R.sup.1).dbd.N--O--, --C(R.sup.1).dbd.N--O--CH.sub.2 --, --N(R.sup.2)--, --CQ--N(R.sup.2)--, --N(R.sup.2)--CQ--, --Q--CQ--N(R.sup.2)--, --N.dbd.C(R.sup.1)--Q--CH.sub.2 --, --N(R.sup.2)--CQ--Q--, --CQ--N(R.sup.2)--CQ--Q--, --N(R.sup.2)--CQ--Q--CH.sub.2 --, --Q--C(R.sup.1).dbd.N--O--CH.sub.2 --, --N(R.sup.2)--C(R.sup.1).dbd.N--O--CH.sub.2 --, --O--CH.sub.2 --C(R.sup.1).dbd.N--O--CH.sub.2 --, --N.dbd.N--C(R.sup.1).dbd.N--O--CH.sub.2 --, --T--Ar.sup.1 or --T--Ar.sup.1 --Q--, where cycloalkylene or heterocycloalkylene (i.e. an aliphatic ring which is doubly attached and in which one or more carbon atoms are replaced by hetero atoms, i.e. atoms other than carbon), alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or cycloalkyl, and substituted alkyl, alkoxy or cycloalkyl and CH.sub.2 --S-- or represents optionally substituted alkanediyl, or dialkylamino. imino grouping ("azamethylene", NH, N-alkyl) and cycloalkyl, aryl or heterocyclyl, where, if alkyl-, halogenoalkyl- or cycloalkyl-substituted alkenediyl or --CH.sub.2 --O--N.dbd.C(R.sup.1)--.
Aryl represents aromatic, mono- or polycyclic hydrocarbon rings such as, for example, phenyl, naphthyl, anthranyl, phenanthryl, preferably phenyl or naphthyl, in particular phenyl.
Heterocyclyl represents saturated or unsaturated, and aromatic, compounds in the form of a ring in which at least one ring member is a hetero atom, i.e. an atom other than carbon. If the ring contains more than one hetero atom, these may be identical or different. Preferred hetero atoms are oxygen, nitrogen or sulphur. The compounds in the form of a ring may form a polycyclic ring system together with other carbocyclic or heterocyclic fused or bridged rings. Preference is given to mono- or bicyclic ring systems, in particular to mono- or bicyclic aromatic ring systems.
Furthermore, it was found that the novel substituted cycloalkenes of the general formula (I) are obtained when ##STR3## in which m, G, R, Y and Z are each as defined above thereof, or with a methoxymethyltriphenylphosphonium halide, the presence of a diluent, to react the keto compounds of the general formula (II) with hydroxylamine or acid adducts thereof to give the corresponding oximes by the method of process a), and then to methylate these by conventional methods, ##STR4## in which m, E, R and Y are each as defined above and (IV), (V) or (VI) ##STR5## in which R.sup.2 and Z are each as defined above and the presence of a diluent, ##STR6## in which m, R and Y are each as defined above, --PO(OR.sup.4).sub.2, ##STR7## in which Z is as defined above and presence of an acid acceptor, ##STR8## in which E, m, Y and R are each as defined above the presence of a diluent, or ##STR9## in which m, Ar.sup.1, E, R and Y are each as defined above and the presence of a diluent, or ##STR10## in which m, G, Y and Z are each as defined above and ##STR11## in which R.sup.7 represents hydrogen, hydroxyl or represents respectively optionally substituted alkyl or alkoxy and the presence of a diluent ##STR12## in which E, G, m, Y and Z are each as defined above, presence of an acid acc
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Dutzmann Stefan
Gayer Herbert
Gerdes Peter
Stenzel Klaus
Tiemann Ralf
Bayer Aktiengesellschaft
Raymond Richard L.
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