Organic compounds -- part of the class 532-570 series – Organic compounds – Sulfur containing
Patent
1998-02-10
2000-04-25
Lee, Howard C.
Organic compounds -- part of the class 532-570 series
Organic compounds
Sulfur containing
424DIG8, 424405, 562840, 568 26, 568 38, C07C32500, A01N 2500
Patent
active
060546212
DESCRIPTION:
BRIEF SUMMARY
The invention relates to novel alkoxyacrylic thiol esters, to a plurality of processes for their preparation and to their use as fungicides, and to novel intermediates and to a plurality of processes for their preparation.
It is already known that certain alkoxyacrylic acid derivatives of a constitution similar to that of the alkoxyacrylic thiol esters described below have fungicidal properties (cf. for example EP-A 226917 or EP-A 370629 or EP-A 398692). However, in many instances, the fungicidal activity of these compounds is unsatisfactory.
This invention, accordingly, provides the novel alkoxyacrylic thiol esters of the general formula (I) ##STR1## in which Ar represents respectively optionally substituted arylene or heterorarylene, respectively optionally halogen-, hydroxyl-, alkyl-, halogenoalkyl- or cycloalkyl-substituted alkanediyl, alkenediyl, alkinediyl or one of the groupings below --, --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.3).dbd.N--O--, --C(R.sup.3).dbd.N--O--CH.sub.2 --, --N(R.sup.4)--, --CQ--N(R.sup.4)--, --N(R.sup.4)--CQ--, --Q--CQ--N(R.sup.4)--, --N.dbd.C(R.sup.3)--Q--CH.sub.2 --, --CH.sub.2 --O--N.dbd.C(R.sup.3)--, --C(CH.sub.3)--O--N.dbd.C(R.sup.3)--, --N(R.sup.4)--CQ--Q--CH.sub.2 --, --N(R.sup.4)--C(R.sup.3).dbd.N--O--CH.sub.2 --, --N.dbd.N--C(R.sup.3).dbd.N--O--CH.sub.2 --, --C(.dbd.N--O--R.sup.5)--C(R.sup.3)--O--N.dbd.CH-- -- or cycloalkylene or heterocycloalkylene (i.e. an aliphatic ring which is doubly attached and where one or more carbon atoms are replaced by hetero atoms, i.e. atoms that differ from carbon), alkyl, alkoxy, alkylthio, alkylamino, dialkylamino or cycloalkyl, and substituted alkyl, alkoxy or cycloalkyl and --CH.sub.2 --S-- or represents optionally substituted alkanediyl, cycloalkyl, aryl or heterocyclyl.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkenyl or alkinyl, are in each case straight-chain or branched, including in combination with hetero atoms, such as in alkoxy, alkylthio or alkylamino.
Halogen generally represents fluorine, chlorine, bromine or iodine, and also pseudohalogens such as, for example, cyano, preferably fluorine, chlorine, bromine or cyano, in particular fluorine or chlorine.
Ary 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, ring-shaped compounds in which at least one ring member is a hetero atom, i.e. in atom different from carbon. If the ring contains more than one hetero atom, these may be identical or different. Preferred hetero atoms are oxygen, nitrogen or sulphur. Optionally, the ring-shaped compounds 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.
Cycloalkyl represents saturated carbocyclic ring-shaped compounds which optionally form a polycyclic ring system together with further carbocyclic fused or bridged rings.
Furthermore, it has been found that the novel alkoxyacrylic thiol esters of the general formula (I) are obtained when (process a)) hydroxyacrylic thiol esters of the general formula (II) ##STR2## in which Ar, G, R.sup.1 and Z are each as defined above, the presence of a diluent.
Finally, it has been found that the novel alkoxyacrylic thiol esters of the general formula (I) have very strong fungicidal activity.
The compounds according to the invention may be present as mixtures of various possible isomeric forms, in particular of stereoisomers, such as, for example, E- and Z-. Both the E- and the Z-isomers, and any mixtures of these isomers, are claimed.
The formula (I) provides a general definition of the alkoxyacrylic thiol esters according to the invention. naphthylene, represents mono- or bicy
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Dutzmann Stefan
Gayer Herbert
Gerdes Peter
Hanssler Gerd
Heinemann Ulrich
Bayer Aktiengesellschaft
Lee Howard C.
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