Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1999-10-13
2000-08-08
Gerstl, Robert
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
548132, A01N 43836, C07D27107
Patent
active
06100281&
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to novel sulphonyloxadiazolones, to a process for their preparation and to their use as microbicides in crop protection and in the protection of materials.
Certain sulphonyloxadiazolones, such as, for example, 4-[(4-chlorophenyl)-sulphonyl]-3-(2,4,6-trimethylphenyl)-1,2,4-oxadiazol-5 (4H)-one, are already known (cf. Zh. Org. Khim 27 (1991), 1262-70). A biological action of these compounds has hitherto not been described.
This invention, accordingly, provides novel sulphonyloxadiazolones of the formula ##STR3## in which
A represents oxygen, sulphur, --SO--, --SO.sub.2 -- or ##STR4## where
R.sup.3 represents hydrogen or alkyl,
R.sup.1 represents optionally substituted cycloalkyl, optionally substituted cycloalkenyl or optionally substituted aryl and
R.sup.2 represents in each case optionally substituted alkyl, alkenyl, dialkylamino or aryl
Furthermore, it has been found that sulphonyloxadiazolones of the formula (I) are obtained when oxadiazolones of the formula ##STR5## in which
A and R.sup.1 are as defined above,
R.sup.2 is as defined above and
X represents halogen, presence of a diluent and if appropriate in the presence of a catalyst.
Finally, it has been found that the sulphonyloxadiazolones of the formula (I) have very good microbicidal properties and can be used both in crop protection and in the protection of materials.
Surprisingly, the sulphonyloxadiazolones of the formula (I) according to the invention exhibit better activity against undesirable microorganisms, in particular fungi, than the constitutionally most similar prior-art compounds of the same direction of action.
The formula (I) provides a general definition of the substances according to the invention.
A also preferably represents oxygen, sulphur, --SO--, --SO.sub.2 -- or ##STR6##
R.sup.3 preferably represents hydrogen or alkyl having 1 to 4 carbon atoms.
R.sup.1 preferably represents cycloalkenyl having 3 to 8 carbon atoms or cycloalkyl having 3 to 8 carbon atoms which in each case is optionally mono- to trisubstituted by identical or different substituents from the group consisting of halogen and alkyl having 1 to 3 carbon atoms.
R.sup.1 furthermore preferably represents aryl having 6 to 10 carbon atoms, where each of these radicals may be mono- to trisubstituted by identical or different substituents from the group consisting of alkylsulphonyl having in each case 1 to 6 carbon atoms; each case 2 to 6 carbon atoms; halogenoalkylthio or halogenoalkylsulphonyl having in each case 1 to 6 carbon atoms and 1 to 5 identical or different halogen atoms; halogenoalkenyloxy having in each case 2 to 6 carbon atoms and 1 to 5 identical or different halogen atoms; alkylcarbonyl, alkoxycarbonyl, hydroximinoalkyl or alkoximinoalkyl having in each case 1 to 6 carbon atoms in the individual alkyl moiety; 1 to 6 carbon atoms and being in this case optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of halogen, and straight-chain or branched alkyl having 1 to 4 carbon atoms and straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms; heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylalkyl, heterocyclylalkyloxy or heterocyclylalkylthio, where these aromatic or heterocyclic radicals may be mono- to trisubstituted by identical or different substituents from the group consisting of atoms, to 5 identical or different halogen atoms, and by straight-chain or branched halogenoalkoxy having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms
R.sup.2 preferably represents alkyl having 1 to 4 carbon atoms, alkenyl having 2 to 4 carbon atoms, halogenoalkyl having in each case 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkenyl having in each case 2 to 4 carbon atoms and 1 to 5 identical or different halogen atoms or represents dialkylamino having in each case 1 to 4 carbon atoms in the two alkyl groups.
R.sup.2 preferably represents aryl having 6 to 10 carbon atoms, whe
REFERENCES:
patent: 3958000 (1976-05-01), Edwards
patent: 3994909 (1976-11-01), Pommer et al.
patent: 5292762 (1994-03-01), Hsu
Assmann Lutz
Deng Chuan-Zheng
Gerdes Peter
Stenzel Klaus
Yuan Li-Ping
Bayer Aktiengesellschaft
Gerstl Robert
Gil Joseph C.
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