Sulphonyloxadiazolones and their use as microbicides

Details Sulphonyloxadiazolones and their use as microbicides Sulphonyloxadiazolones and their use as microbicides

1999-10-13

2000-10-24

Gerstl, Robert

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

548132, C07D41312, A01N 43836

Patent

active

06136830&

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, substituted cycloalkenyl or optionally substituted aryl and
Furthermore, it has been found that sulphonyloxadiazolones of the formula (I) are obtained when ##STR5## in which A and R.sup.1 are as defined above, presence of a diluent.
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. ##STR6## R.sup.3 preferably represents hydrogen or alkyl having 1 to 4 carbon atoms. cycloalkyl having 3 to 8 carbon atoms which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of halogen and alkyl having 1 to 3 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 moieties; 1 to 6 carbon atoms and being in each case optionally mono- to tetrasubstituted by identical or different substituents from the group consisting of halogen, 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 1 to 9 identical or different halogen atoms. members and 1 to 3 heteroatoms, such as nitrogen, oxygen and/or, where this radical may be mono- to trisubstituted by identical or different substituents from the group consisting of halogen, cyano, nitro, amino, hydroxyl, alkyl having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogenoalkyl having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, halogenoalkoxy having 1 to 4 carbon atoms and 1 to 5 identical or different halogen atoms, alkylcarbonyl having 1 to 4 carbon atoms in the alkyl moiety, alkoxycarbonyl having 1 to 3 carbon atoms in the alkoxy moiety, carbamoyl, alkyaminocarbonyl having 1 to 4 carbon atoms in the alkyl moiety, dialkylaminocarbonyl having 1 to 4 carbon atoms in the individual alkyl moieties, hydroximinoalkyl or alkoximinoalkyl having in each case 1 to 4 carbon atoms in the individual alkyl moieties and cycloalkyl having 3 to 6 carbon atoms.
Heterocyclyl represents cyclic compounds in which at least one ring member is a heteroatom, i.e. an atom different from carbon. If the ring contains a plu

REFERENCES:
patent: 3994909 (1976-11-01), Pommer et al.
patent: 4420486 (1983-12-01), Ohyama et al.
Database WPI, Section Ch, Week 8722, Derwent Pulications Ltd., London, GB; Class C02, AN 87-154900, XP002073605, -&JP 62 093 283 A (Idemitsu Kosan Co Ltd), siehe Zusammenfassung.

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