Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1998-03-12
1999-09-21
Raymond, Richard L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
546159, 546162, C07D21542, C07D40112, A01N 4342
Patent
active
059554738
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
Field of the Invention
The present invention relates to quinolines of the formula I ##STR2## where the substituents have the following meanings: R.sup.1, R.sup.2, R.sup.3, R.sup.4 in each case independently of one another are hydrogen, hydroxyl, nitro, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -haloalkylthio, C.sub.1 -C.sub.4 -alkoxyalkyl, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio; -alkylcarbonyl, C.sub.1 -C.sub.4 -alkoxycarbonyl; -alkenyl, C.sub.2 -C.sub.8 -alkynyl or C.sub.1 -C.sub.8 -alkylcarbonyl, it being possible for these groups to be partially or fully halogenated, C.sub.3 -C.sub.7 -cycloalkyl or C.sub.3 -C.sub.7 -cycloalkenyl, it being possible for these radicals to be partially or fully halogenated, them one to three of the following groups: nitro, halogen, cyano, 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, C.sub.1 -C.sub.4 -alkylamino, di-C.sub.1 -C.sub.4 -alkylamino, C.sub.1 -C.sub.4 -alkylsulfonyl, C.sub.1 -C.sub.4 -alkylsulfoxy, C.sub.1 -C.sub.4 -alkylsulfonyloxy, C.sub.1 -C.sub.4 -alkylcarbonyl, C.sub.1 -C.sub.4 -alkylcarbonyloxy, C.sub.1 -C.sub.4 -alkoxycarbonyl, aryl, aryloxy; attached to them one to three of the following groups: nitro, halogen, cyano, 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, C.sub.1 -C.sub.4 -alkylamino, di-C.sub.1 -C.sub.4 -alkylamino, C.sub.1 -C.sub.4 -alkylsulfonyl, C.sub.1 -C.sub.4 -alkylsulfoxy, C.sub.1 -C.sub.4 -alkylsulfonyloxy, C.sub.1 -C.sub.4 -alkylcarbonyl, C.sub.1 -C.sub.4 -alkylcarbonyloxy, C.sub.1 -C.sub.4 -alkoxycarbonyl, aryl or aryloxy, where the cyclic substituents, in turn, can have attached to them one to three of the following substituents: halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkylamino, di-C.sub.1 -C.sub.4 -alkylamino, C.sub.1 -C.sub.4 -alkylsulfonyl, C.sub.1 -C.sub.4 -alkylsulfoxy, C.sub.1 -C.sub.4 -alkylsulfonyloxy, C.sub.1 -C.sub.4 -alkylcarbonyl, C.sub.1 -C.sub.4 -alkylcarbonyloxy, C.sub.1 -C.sub.4 -alkoxycarbonyl, aryl, aryloxy; formula I, with the exception of the compounds where the radicals are defined as follows:
______________________________________ 1 a-d R.sup.1,2,3,4,5,6,7,8 = H; R.sup.9 = C.sub.6 H.sub.5, 4-Cl--C.sub.6
H.sub.4,
2,4-di-Cl--C.sub.6 H.sub.3, 2,4-di-Br--C.sub.6 H.sub.3,
1 e-h R.sup.1,2,3,4,5,6,7,8 = H; R.sup.9 = 4-Cl--C.sub.6 H.sub.4,
2,4-di-Cl--C.sub.6 H.sub.3, in
each case in the form of the N-oxide and the HCl salt,
1 i R.sup.1,2,3,4,5,6,7,8 = H; R.sup.9 = 4-Br--C.sub.6 H.sub.4 HBr
salt
1 j-k R.sup.1,2,3,4,6,8 = H; R.sup.5 = CH.sub.3 ; R.sup.7 = H, CH.sub.3 ;
R.sup.9 = C.sub.6 H.sub.5
1 m R.sup.1,3,4,6,7,8 = H; R.sup.2,5 = CH.sub.3 ; R.sup.9 = C.sub.6
H.sub.5,
1 n R.sup.1 = O--CH.sub.3 ; R.sup.2,3,4,6,7,8 = H; R.sup.5 = CH.sub.3 ;
R.sup.9 = C.sub.6 H.sub.5
HCl salt,
1 o-q R.sup.1,3,4,5,6,7,8 = H; R.sup.2 = CH.sub.3 ; R.sup.9 = 4-NO.sub.2
--C.sub.6 H.sub.4 ;
HCl salt, N-oxide
1 r-s R.sup.1,2,4,5,6,7,8 = H; R.sup.3 = Cl; R.sup.9 = 4-NO.sub.2
--C.sub.6 H.sub.4,
4-Cl--C.sub.6 H.sub.4
1 t-u R.sup.1,2,3,4,6,7,8 = H; R.sup.5 = Cl; R.sup.9 = 4-Cl--C.sub.6
H.sub.4,
2,4-di-Cl--C.sub.6 H.sub.3
1 v-x R.sup.1,4,6,7 = H; R.sup.3 = H,; R.sup.2 = H,CH.sub.3 O; R.sup.5 =
CH.sub.3
R.sup.8,9 = CH.sub.2 CH.sub.2 Cl HCl salt,
1 x R.sup.1,4,6,7 = H; R.sup.3 = Cl R.sup.2 = H; R.sup.5 = CH.sub.3
R.sup.8,9 =
CH.sub.2 CH.sub.2 Cl HCl salt,
1 y R.sup.1,4,6,7 = H; R.sup.3 = H; R.sup.2 = Cl; R.sup.5 = H R.sup.8,9
=
CH.sub.2 CH.sub.2 Cl HCl salt,
1 z R.sup.1,2,4,5,6,7,8 = H; R.sup.3 = Cl; R.sup.9 = CH.sub.2 -3-Py,
2 a-b R.sup.1,2,3,4,5,6,7,8 = H; R.sup.9 = quinolin-4-yl, di-N-oxide,
2
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Reznikov et al., Chemical Abstract, vol. 123, No. 17, Oct. 23, 1995, 228065u.
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Ammermann Eberhard
Eicken Karl
Lorenz Gisela
Strathmann Siegfried
Wagner Oliver
BASF - Aktiengesellschaft
Rao Deepak R.
Raymond Richard L.
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