Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1996-09-24
1997-12-30
Ramsuer, Robert W.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
548204, 548205, 106 1416, 106 1833, A01N 4378, C07D41704
Patent
active
057031037
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP96/01032 filed Mar. 20, 1995.
The present invention relates to novel thiazolylpyrazolinones, a process for their preparation and their use for the protection of technical materials.
Thiazolylpyrazolinones are known and are described, e.g., in JP-2 149 617, Indian. J. Chem. 21 B, 869 (1982), Synth. Com. 23, 1855 (1993), J. heterocyclic Chem. 27, 865 (1990) and DD-150 203. However, their use for the protection of industrial materials has not been disclosed.
The application relates to novel thiazolylpyrazolinone derivatives of the formula ##STR1## in which hydrogen, alkyl or halogen, and alkinyl, cycloalkyl, cycloalkenyl, alkyl (cycloalkyl), alkenyl (cycloalkenyl), alkoxy, alkylthio, aralkoxy, aralkylthio, aralkyl, aryl, hetaryl, aryloxy, hetaryloxy, arylthio, hetarylthio, alkoxycarbonyl, alkoxycarbonalalkyl or cyanoalkyl, or their acid addition products or metal salt complexes.
In the present application:
Alkyl preferably denotes straight-chain or branched, unsubstituted or substituted alkyl having 1 to 18 C atoms, such as Me, Et, n-, i-propyl, n-, i-, s- and tert-butyl, n-, i- and tert-pentyl, n-hexyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetrad ecyl, n-pentadecyl, n-hexadecyl, n-heptodecyl or n-octadecyl or their branched structural isomers.
Suitable substituents are preferably halogen, such as chlorine and/or fluorine.
An alkyl radical can also be interrupted by 1 to 2 heteroatoms such as oxygen or sulphur, or atom groups such as N-Me, N-Et, --S(O), --SO.sub.2, without the total number of atoms changing.
Alkenyl (+alkinyl) is preferably defined as alkyl, changed only to the extent that at least one and at most three C--C single bonds have been replaced by a C--C double (triple) bond. The number of C atoms is at least three and is increased by at least two C atoms with each further double bond (triple bond) which is added.
Cycloalkyl and cycloalkenyl groups include cycloalkyl having preferably 3 (5) to 7 C atoms, such as cyclopropyl, cyclobutyl, cycloheptyl, cyclopentyl, cyclopentenyl, cyclohexenyl, cyclohexyl; preferred substituted cycloalkyl groups include cycloalkyl substituted by 1 to 3 C.sub.1 -C.sub.4 -alkyl groups or 1 to 3 halogen atoms, such as chlorine and/or fluorine, such as methylcyclohexyl, dimethylcyclohexyl, 1,3,3-trimethylcyclohexyl, 3-chlorocyclohexyl. Alkyl(cycloalkyl) (and alkyl(cycloalkenyl) groups) preferably contain 1 to 6 C atoms in the straight-chain or branched alkyl moiety and 3 (5) to 7 atoms in the cycloalkyl/alkenyl moiety; particularly (1-cyclopentyl)methyl, (1-cyclopentenyl)methyl, (1-cyclohexenyl)methyl, (1-cyclohexyl)methyl, (1-cyclopropyl)methyl.
Alkoxycarbonyl represents straight-chain or branched alkoxycarbonyl preferably having 1 to 6 C atoms in the alkoxy radical, such as methoxycarbonyl, ethoxycarbonyl, n- and i-propoxycarbonyl, n-, i-, sec- and tert-butoxycarbonyl, hexoxycarbonyl. Analogous meanings apply to the alkoxycarbonylalkyl groups.
Aralkyl preferably contains 1 to 6, in particular 1 to 4, C atoms in the straight-chain or branched alkyl moiety and preferably contains phenyl or naphthyl as aryl moiety.
Examples of aralkyl groups of this type include benzyl, .alpha.-methyl benzyl, .alpha.,.alpha.-dimethylbenzyl, 2-phenethyl, .alpha.- and .beta.-naphthylmethyl. These aralkyl radicals can bear 1 to 3 substituents selected from the group consisting of halogen (in particular chlorine and/or fluorine), nitro, cyano, nonhalogenated or halogenated C.sub.1 -C.sub.4 -alkyl or -alkoxy, such as methyl, ethyl, trifluoromethyl, difluorochloromethyl, difluoromethyl, trichloromethyl, methoxy, ethoxy, trifluoromethoxy, difluorochloromethoxy and difluoromethoxy, non-halogenated or halogenated C.sub.1 -C.sub.4 -alkylmercapto, such as methylmercapto, trifluoromethylmercapto, difluorochloromethylmercapto.
The term aryl is to be taken to mean unsubstituted or substituted aryl preferably having 6 to 12 C atoms in the aryl moiety. Preferred examples include phenyl, biphenyl and naphthyl. The aryl groups can bear 1 to 3 subs
REFERENCES:
Singh et al, Chemical Abstracts, vol. 120, No. 32 3362 (1994).
Indian J. Heterocycl. Chem 3(1), 5-8 (1993).
Singh et al, Chemical Abstracts, vol. 120, No. 8516g (1994).
Sawhney et al, Chemical Abstracts, vol. 98, No. 125958y (1983).
Richter et al, Chemical Abstracts, vol. 96, No. 52303c (1982).
Heuer Lutz
Kugler Martin
Sasse Klaus
Schrage Heinrich
Wachtler Peter
Bayer Aktiengesellschaft
Ramsuer Robert W.
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