Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1998-02-17
2000-06-13
Clardy, S. Mark
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
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Patent
active
060750235
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to a method for controlling fish mycoses and single-cell ectoparasites on fish, which comprises using an active compound suitable for inhibiting the mitochondrial respiratory chain at the stage of the b/c.sub.1 complex.
The invention additionally relates to compounds of the formula IA or IB ##STR1## where . . . is a single or double bond and the index and the substituents have the following meanings:
R' is --C[CO.sub.2 CH.sub.3 ].dbd.CHOCH.sub.3, --C[CO.sub.2 CH.sub.3 ].dbd.NOCH.sub.3, --C[CONHCH.sub.3 ].dbd.NOCH.sub.3, --C[CO.sub.2 CH.sub.3 ].dbd.CHCH.sub.3, --C[CO.sub.2 CH.sub.3 ].dbd.CHCH.sub.2 CH.sub.3, --C[COCH.sub.3 ].dbd.NOCH.sub.3, --C[COCH.sub.2 CH.sub.3 ].dbd.NOCH.sub.3, --N(OCH.sub.3)--CO.sub.2 CH.sub.3, --N(CH.sub.3)--CO.sub.2 CH.sub.3, --N(CH.sub.2 CH.sub.3)--CO.sub.2 CH.sub.3,
R" is a C-organic radical, or alkylamino group, or an unsubst. or subst. bicyclic, partially or completely unsaturated system which, in addition to carbon ring members, can contain heteroatoms from the group consisting of oxygen, sulfur and nitrogen,
R.sup.x is --OC[CO.sub.2 CH.sub.3 ].dbd.CHOCH.sub.3, --OC[CO.sub.2 CH.sub.3 ].dbd.CHCH.sub.3, --OC[CO.sub.2 CH.sub.3 ].dbd.CHCH.sub.2 CH.sub.3, --SC[CO.sub.2 CH.sub.3 ].dbd.CHOCH.sub.3, --SC[CO.sub.2 CH.sub.3 ].dbd.CHCH.sub.3, --SC[CO.sub.2 CH.sub.3 ].dbd.CHCH.sub.2 CH.sub.3, --N(CH.sub.3)C[CO.sub.2 CH.sub.3 ].dbd.CHOCH.sub.3, --N(CH.sub.3)C[CO.sub.2 CH.sub.3 ].dbd.NOCH.sub.3, --CH.sub.2 C[CO.sub.2 CH.sub.3 ].dbd.CHOCH.sub.3, --CH.sub.2 C[CO.sub.2 CH.sub.3 ].dbd.NOCH.sub.3, --CH.sub.2 C[CONHCH.sub.3 ].dbd.NOCH.sub.3,
R.sup.y is oxygen, sulfur, .dbd.CH--or .dbd.N--,
n is 0, 1, 2 or 3, where the radicals X can be different if n>1;
X is cyano, nitro, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio or, in the case where n>1, a C.sub.3 -C.sub.5 -alkylene, C.sub.3 -C.sub.5 -alkenylene, oxy-C.sub.2 -C.sub.4 -alkylene, oxy-C.sub.1 -C.sub.3 -alkylenoxy, oxy-C.sub.2 -C.sub.4 -alkenylene, oxy-C.sub.2 -C.sub.4 -alkenylenoxy or butadienediyl group bonded to two adjacent C atoms of the phenyl ring, where these chains in turn can carry one to three of the following radicals: halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy or C.sub.1 -C.sub.4 -alkylthio,
Y is .dbd.C-- or --N--,
Q is phenyl, pyrrolyl, thienyl, furyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, thiadiazolyl, triazolyl, pyridinyl, 2-pyridonyl, pyrimidinyl or triazinyl,
T is phenyl, oxazolyl, thiazolyl, thiadiazolyl, oxadiazolyl, pyridinyl, pyrimidinyl or triazinyl, controlling fish mycoses and for controlling single-cell ectoparasites and costiasis.
To date, only a few substances are known which are suitable for controlling fish mycoses and single-cell ectoparasites.
The preparation Malachite Green used mainly until now had to be taken off the market because of its teratogenicity [cf. Meyer et al., Transactions of the American Fisheries Society, 112, 818-824] and suspicion of carcinogenicity. Other products (eg. formalin, potassium permanganate, sodium chloride) are only slightly active and in some cases have undesirably severe effects on the environment. Regarding the existing possibilities of controlling fish parasites, see W. Schaperclaus, Fischkrankheiten (2nd part), 4th edition, Akademie-Verlag Berlin, 1979 and H.-H. Reichenbach-Klinke, Reichenbach-Kline's Fish Pathology, T.S.H. Publications Inc. Ltd., 1973.
Active compounds which inhibit the mitochondrial respiratory chain at the stage of the b/c.sub.1 complex are known from the literature as fungicides [cf. Dechema monographs Vol. 129, 27-38, VCH Verlagsgemeinschaft Weinheim 1993; Natural Product Reports 1993, 565-574; Biochem. Soc. Trans. 22, 63S (1993)].
In particular, representatives of the active compounds of the formula I (or IA and IB) having fungicidal and in some cases also bioregulatory action are described in the following patents:
EP-A 178 826,
REFERENCES:
patent: 3152953 (1964-10-01), Strong et al.
patent: 4826842 (1989-05-01), Mehlhorn et al.
patent: 4829085 (1989-05-01), Wenderoth et al.
patent: 4959484 (1990-09-01), Daum et al.
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Clough, Natural Product Reports, 1993,pp. 565-574.
Roehl et al., Biochem. Soc. Trans., vol. 22, 1993, p. 63S.
Kohle et al., Biochem. Soc. Trans., vol. 22, 1993, p. 65S.
Chem. Abst., vol. 96, No. 13, 1982, Abs. No. 99524r.
Dohmen Gerhard Peter
Kunast Christoph
Munk Reinhart
Rothhaas Gerhard
BASF - Aktiengesellschaft
Clardy S. Mark
Pryor Alton
LandOfFree
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