Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1998-05-18
2000-04-25
Raymond, Richard L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
5142225, 5142238, 5142272, 5142278, A01N 4740, A01N 5100
Patent
active
060544546
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to the use of compounds of formula ##STR2## wherein
A is an unsubstituted or mono- to tetrasubstituted, aromatic or non-aromatic, monocyclic or bicyclic heterocyclic radical, where one to two of the substituents of A can be selected from the group consisting of halo-C.sub.1 -C.sub.3 alkyl, cyclopropyl, halocyclopropyl, C.sub.2 -C.sub.3 alkenyl, C.sub.2 -C.sub.3 alkynyl, halo-C.sub.2 -C.sub.3 alkenyl, halo-C.sub.2 -C.sub.3 alkynyl, halo-C.sub.1 -C.sub.3 alkoxy, C.sub.1 -C.sub.3 alkylthio, halo-C.sub.1 -C.sub.3 alkylthio, allyloxy, propargyloxy, allylthio, propargylthio, haloallyloxy, haloallylthio, cyano and nitro, and one to four of the substituents of A can be selected from the group consisting of C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkoxy and halogen;
R is hydrogen, C.sub.1 -C.sub.6 alkyl, phenyl-C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 cycloalkyl, C.sub.2 -C.sub.6 alkenyl or C.sub.2 -C.sub.6 alkynyl;
X is N--NO.sub.2 or N--CN,
in the free form or in salt form or, if appropriate, tautomers thereof, in the free form or in salt form, for controlling fish parasites, in particular sea lice. The invention also relates to a method of controlling these parasites as well as to the use of these compounds or tautomers for the preparation of corresponding antiparasitic compositions.
The compounds of formula I are known and are disclosed, inter alia, in EP-A-0 580 553.
Intensive fish farming sustains substantial economical losses through the injury of fish by parasites. Treatments against these parasites are known; the conventional active substances, however, must be used in relatively high concentrations and require long treatment periods. These active substances therefore cannot fully meet the requirements of a gentle treatment, which is why there is still a need for the provision of further compounds having fish parasite-controlling properties, in particular for controlling fish-parastic crustaceans, which object is achieved according to this invention by the use of compounds I.
Some of the compounds I can exist in the form of tautomers. If, for example, R is hydrogen, then corresponding compounds I, i.e. those having a 3-H-4-imino-perhydro-1,3,5oxadiazine part-structure, can exist in an equilibrium with the relevant tautomers, which have a 4-amino-1,2,5,6-tetrahydro-1,3,5-oxadiazine part-structure. Accordingly, the compounds I hereinabove and hereinafter are, where appropriate, also to be understood as meaning corresponding tautomers, even when no specific mention is made of the latter in each individual case.
Compounds I which have at least one basic centre can form, for example, acid addition salts. These acid addition salts are formed, for example, with strong inorganic acids, such as mineral acids, typically perchloric acid, sulfuric acid, nitric acid, nitrous acid, a phosphoric acid or a hydrohalic acid, with strong organic carboxylic acids, such as unsubstituted or substituted, for example halogen-substituted, C.sub.1 -C.sub.4 alkanecarboxylic acids, for example acetic acid, as well as unsaturated or saturated dicarboxylic acids, typically oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid or phthalic acid, or hydroxycarboxylic acids, for example ascorbic acid, lactic acid, malic acid, tartaric acid or citric acid, or benzoic acid, or with organic sulfonic acids, such as unsubstituted or substituted, for example halogen-substituted, C.sub.1 -C.sub.4 alkane- or arylsulfonic acids, typically methane- or p-toluenesulfonic acid. Compounds I which have at least one acidic group can furthermore form salts with bases. Suitable salts with bases are, for example, metal salts such as alkali metal salts or alkaline earth metal salts, typically sodium salts, potassium salts or magnesium salts, or salts with ammonia or with an organic amine, such as morpholine, piperidine, pyrrolidine, a mono-, di- or tri-lower alkylamine, for example ethyl-, diethyl-, triethyl- or dimethylpropylamine, or a mono-, di- or trihydroxy-lower alkylamine, for example mono-, di- or triethano
REFERENCES:
patent: 5504081 (1996-04-01), Lohr et al.
Hess Ernst
Schmid Hariolf
Morris Michael P.
Novartis Corporation
Raymond Richard L.
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