Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1997-07-07
1998-12-01
Ramsuer, Robert W.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
5483717, 5483725, A01N 4356, C07D23140
Patent
active
058439781
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP95/05148 filed Dec. 28, 1995.
The present invention relates to new acylated 5-aminopyrazoles, to processes for their preparation, and to their use for controlling animal pests, in particular insects, arachnids and nematodes found in agriculture, in forests, in the protection of stored products and of materials, and in the hygiene sector.
It has already been disclosed that certain 1-aryl-5-aminopyrazole derivatives (cf., for example, EP-A 0 257 479 and EP-A 0 243 636) have insecticidal and acaricidal properties.
However, efficacy and spectrum of action of these compounds is not always entirely satisfactory, in particular when low rates and concentrations are applied.
There has now been found new acylated 5-aminopyrazoles of the formula (I) ##STR2## in which R.sup.1 represents alkyl, alkoxyalkyl or halogenoalkyl, alkoxycarbonyl or alkenyloxycarbonyl,
Furthermore, it has been found that the acylated 5-aminopyrazoles of the formula (I) are obtained when ##STR3## in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the abovementioned meaning are reacted with acid halides of the formula (III) diluent; or ##STR4## in which R.sup.1, R.sup.3, R.sup.4 and R.sup.5 have the abovementioned meaning are reacted diluent and if appropriate in the presence of a catalyst, or diluent.
Finally, it has been found that the new acylated 5-aminopyrazoles of the formula (I) have pronounced biological properties and are suitable, above all, for controlling animal pests, in particular insects, arachnids and nematodes, which are found in agriculture, in forests, in the protection of stored products and of materials, and in the hygiene sector.
Formula (I) provides a general definition of the acylated 5-aminiopyrazoles according to the invention.
Preferred substituents or ranges of the radicals given in the formulae mentioned hereinabove and hereinbelow are illustrated in the following text. -alkoxy-C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -halogenoalkyl. trifluoromethylthio, difluoromethylthio, C.sub.1 -C.sub.4 -alkoxycarbonyl or C.sub.2 -C.sub.4 -alkenyloxycarbonyl. C.sub.3 -C.sub.6 -cycloalkyl which is optionally substituted by halogen or C.sub.1 -C.sub.4 -alkyl. represents C.sub.3 -C.sub.6 -cycloalkyl which is optionally substituted by halogen or C.sub.1 -C.sub.4 -alkyl. by halogen or C.sub.3 -C.sub.6 -cycloalkyl. optionally monosubstituted to trisubstituted by identical or different substituents, suitable substituents being halogen, nitro, cyano, C.sub.1 -C.sub.12 -alkyl, C.sub.1 -C.sub.12 -alkoxy, C.sub.1 -C.sub.12 -alkylthio, C.sub.1 -C.sub.12 -halogenoalkyl, C.sub.1 -C.sub.12 -halogenoalkoxy, C.sub.1 -C.sub.12 -halogenoalkylthio, C.sub.2 -C.sub.12 -alkenyl, C.sub.1 -C.sub.12 -alkoxy-C.sub.2 -C.sub.12 -alkenyl, C.sub.1 -C.sub.4 -alkylthio-C.sub.2 -C.sub.12 -alkenyl, C.sub.2 -C.sub.12 -halogenoalkenyl, and also phenyl, phenoxy, phenylthio or benzyl, each of which is optionally monosubstituted to trisubstituted by identical or different substituents from the series consisting of halogen, nitro, cyano, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -halogenoalkyl, C.sub.1 -C.sub.4 -halogenoalkoxy or C.sub.1 -C.sub.4 -halogenoalkylthio. n-, i-, s- or t-butyl; or represents methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, trifluoromethyl, difloromethyl, fluoromethyl, 1-chloro-1-ethyl or 1-fluoro-1-ethyl. bromine, cyano, nitro, trifluoromethylthio, difluoromethylthio, methoxycarbonyl. ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl or allyloxycarbonyl. i-, s- or t-butyl, or represents cyclopropyl, cyclopentyl or cyclohexyl, each of which is optionally substituted by fluorine, chlorine, methyl and/or ethyl. i-propyl, n-, i-, s- or t-butyl, or represents cyclopropyl, cyclopentyl or cyclohexyl, each of which is optionally substituted by fluorine, chlorine, methyl and/or ethyl. CH.sub.2 --, --CH(C.sub.2 H.sub.5)--, --CH(C.sub.3 H.sub.7 --i)--, --CHF--, CHCl-- or --CH(cyclopropyl)-. is optionally monosubstituted to trisubsti
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Erdelen Christoph
Heil Markus
Wernthaler Konrad
Bayer Aktiengesellschaft
Ramsuer Robert W.
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