Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1999-10-14
2000-07-18
Gerstl, Robert
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
548132, 5462691, A01N 4382
Patent
active
060908319
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to the use of sulphonyloxadiazolones, some of which are known, as microbicides in crop protection and in the protection of materials. Moreover, the invention also relates to novel sulphonyloxadiazolones and to a process for their preparation.
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), 1262-1270). However, a biological action of these compounds has hitherto not been described.
It has now been found that sulphonyloxadiazolones of the formula ##STR5## in which A represents a single bond or represents alkanediyl, alkenediyl, alkinediyl or a grouping --*O--CH.sub.2 --, --*O--CH.sub.2 --CH.sub.2 --, --*CH.sub.2 --O--, --*CH.sub.2 --O--CH.sub.2 --CH.sub.2 --, --*CH.sub.2 S--, --*S--CH.sub.2 --, ##STR6## or ##STR7## where the atom labelled by * is in each case attached to R.sup.1 and substituted cycloalkenyl, optionally substituted aryl or optionally substituted heterocyclyl and dialkylamino, aryl or heterocyclyl, protection and in the protection of materials.
Surprisingly, the sulphonyloxadiazolones of the formula (I) to be used according to the invention show considerably better activity against undesirable microorganisms, in particular fungi, than the constitutionally most similar prior-art substances of the same direction of action.
The formula (I) provides a general definition of the substances to be used according to the invention.
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 plurality of heteroatoms, these can be identical or different. Preferred heteroatoms are oxygen, nitrogen or sulphur. If the ring contains a plurality of oxygen atoms, these are not adjacent. 4 carbon atoms, alkenediyl having 2 to 4 carbon atoms, alkinediyl having 2 to 4 carbon atoms or a grouping --*O--CH.sub.2 --, --*O--CH.sub.2 --CH.sub.2 --, --*CH.sub.2 --O--, --*CH.sub.2 --O--CH.sub.2 --CH.sub.2 --, --*CH.sub.2 --S--, --*S--CH.sub.2 --, ##STR8## or ##STR9## where the atom labelled by * is in each case attached to R.sup.1. R.sup.3 preferably represents hydrogen or alkyl having 1 to 4 carbon atoms. to 8 carbon atoms or cycloalkenyl having 3 to 8 carbon atoms, each of 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 from 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. heterocyclyl radical having 5 or 6 ring members and 1 to 3 heteroatoms which may optionally 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
REFERENCES:
patent: 3994909 (1976-11-01), Pommer et al.
patent: 4420486 (1983-12-01), Ohyama et al.
Database WPI, Section Ch, Week 8722, Derwent Publications Ltd., London, GB; Class C02, AN 87-154900, XP002073605 -& JP 62 093 283 A (Idemitsu Kosan Co Ltd) siehe Zusammenfassung.
Zh. Org. Khim., 27, 1991, A.A. Ecunehko et al, pp. 1262-1270.
Synthesis, Jun. 6, 1983, Editors G. Schill, G. Sosnovsky and H.J. Ziegler, Communications pp. 483-486.
J. Heterocyclic Chem., Jun. 10, 1973, pp. 357-362, Synthesis of 4(5)-Substituted 2-Amino-5(4)-Hydroxyimino-5(4)H-imidazoles and Their Transformation into the Corresponding 3-Substituted 5-Amino-1,2,4-oxadiaoles, Bruno Cavalleri etal.
Journal of Organic Chemistry, vol. 41, Sep.-Dec. 1976, pp. 3233-3237, Babu George et al, Heterocycles from N-Ethoxycarbonylthioamides and Einucleophilic Reagents, 1. Dihydro-1,2,4-triazolones and 1,2,4-Oxadiazolones.
J. Heterocyclic Chem., 30, (5), Oct.-Nov. 1993, pp. 1253-1260, Heterocyclic Amino Acids as Synthons, Reactions with Dicarbonyl Compounds, Patrik Kolar et al.
J. Heterocyclic Chem., Aug. 1981, pp. 997-1006, Some Heterocyclic Sulfonyl Chlorides and Derivative, kRichard J. Cremlyn et al.
Assmann Lutz
Gerdes Peter
Stenzel Klaus
Bayer Aktiengesellschaft
Gerstl Robert
Gil Joseph C.
LandOfFree
Use of sulfonyloxadiazolones as microbicides does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Use of sulfonyloxadiazolones as microbicides, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Use of sulfonyloxadiazolones as microbicides will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2037500