Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1994-11-10
1996-05-28
McKane, Joseph K.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514427, 548524, 548557, 548561, 548562, A61K 31395, C07D20730
Patent
active
055212115
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP93/01231 filed May 17, 1993.
The present invention relates to novel substituted 2-arylpyrroles, intermediates for their preparation and their use for combating animal pests, in particular insects, arachnids and nematodes, encountered in agriculture, in forestry, in the protection of stored products and of materials, and in the hygiene field.
It is known already that structurally similar cyanopyrroles are effective as molluscicides, fungicides and insecticides (see in this context e.g. EP-A 0 347 488, EP-A 0 358 047, EP-A 0 312 723, DE-A 4 117 752). However, the efficacy and range of effect of these compounds is not always completely satisfactory, in particular when using low quantities and concentrations.
Novel substituted 2-arylpyrroles of the general formula (I) have now been found ##STR2## in which
R.sup.1 represents cyano or nitro,
R.sup.2 and R.sup.3, independently of each other, represent hydrogen, in each case optionally substituted alkyl, alkenyl, alkinyl, alkoxycarbonyl, alkenoxycarbonyl, alkinoxycarbonyl or alkylcarbonyl or where the radicals R.sup.2 and R.sup.3, together with the nitrogen atom enclosed by them, form a ring,
R.sup.4 represents hydrogen, phenyl or optionally substituted alkyl,
Ar represents, in each case optionally substituted, phenyl or naphthyl,
Y.sup.1 represents halogen and
Y.sup.2 represents optionally substituted alkyl or halogen.
Furthermore it has been found that the substituted 2-arylpyrroles of the general formula (I), in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, Ar, Y.sup.1 and Y.sup.2 have the abovementioned meaning, are obtained ##STR3## in which
R.sup.1, Ar, Y.sup.1 and Y.sup.2 have the abovementioned meaning, are reacted with compounds of the formula (III) ##STR4## in which
R.sup.2, R.sup.3 and R.sup.4 have the abovementioned meaning and
X represents an anionic leaving group, diluents.
Finally it was found that novel substituted 2-arylpyrroles of the formula (I) possess strongly pronounced biological properties and are suitable in particular for combating animal pests, in particular insects, arachnids and nematodes, encountered in agriculture, in forestry, in the protection of stored products and of materials, and in the hygiene field.
The novel substituted 2-arylpyrroles according to the invention are defined by the general formula (I).
2-Arylpyrroles of the above formula (I) are preferred in which
R.sup.1 represents cyano or nitro,
R.sup.2 and R.sup.3, independently of each other, either represent hydrogen, C.sub.1 -C.sub.8 -alkyl, C.sub.3 -C.sub.8 -alkenyl or C.sub.3 -C.sub.8 -alkinyl, where the alkyl, alkenyl or alkinyl radicals are optionally substituted by 1 to 6 identical or different halogen atoms, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkylthio, (C.sub.1 -C.sub.6 -alkyl)carbonyloxy, (C.sub.1 -C.sub.6 -alkoxy)-carbonyl, optionally substituted phenyl, cyano or nitro, or represent (C.sub.1 -C.sub.8 -alkoxy)-carbonyl, (C.sub.3 -C.sub.8 -alkenoxy)-carbonyl or (C.sub.3 -C.sub.8 -alkinoxy)-carbonyl, where the alkoxy, alkenoxy or alkinoxy moiety is in each case optionally substituted by 1 to 6 identical or different radicals from the series halogen, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkylthio, (C.sub.1 -C.sub.6 -alkyl)carbonyloxy, (C.sub.1 -C.sub.6 -alkoxy)-carbonyl, optionally substituted phenyl, cyano or nitro, or represent (C.sub.1 -C.sub.8 -alkyl)carbonyl, which is optionally substituted by 1-6 identical or different radicals from the series halogen, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkylthio, (C.sub.1 -C.sub.6 -alkyl)carbonyloxy, (C.sub.1 - C.sub.6 -alkoxy)-carbonyl, optionally substituted phenyl, cyano or nitro, or R.sup.2 and R.sup.3, together with the nitrogen enclosed by them, form a 4- to 8-membered ring,
R.sup.4 represents hydrogen, phenyl or C.sub.1 - to C.sub.8 -alkyl, which is optionally substituted by 1 to 6 radicals from the series halogen, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -alkylthio, (C.sub.1 -C.sub.6 -alkyl)carbonyloxy, (C.sub.1 -C.sub.6 -alkoxy)-carbonyl, phenyl, cyano or nit
REFERENCES:
patent: 4929634 (1990-05-01), Herman et al.
patent: 5010098 (1991-04-01), Brown et al.
patent: 5030735 (1991-07-01), Addor et al.
patent: 5118816 (1992-06-01), Doehner, Jr. et al.
patent: 5130328 (1992-07-01), Kameswaran
patent: 5192794 (1993-03-01), Uhr et al.
patent: 5194630 (1993-03-01), Kameswaran et al.
patent: 5233051 (1993-08-01), Uhr et al.
CA 117:212309s Preparation of . . . agents. Kameswaran et al., p. 823, 1992.
CA 120:217699r Preparation of . . . pesticides. Uhr et al., p. 1085, 1994.
Erdelen Christoph
Stendel Wilhelm
Uhr Hermann
Wachendorff-Neumann Ulrike
Bayer Aktiengesellschaft
Gerstenzang William C.
McKane Joseph K.
LandOfFree
Substituted 2-arylpyrroles does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Substituted 2-arylpyrroles, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Substituted 2-arylpyrroles will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-787262