Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1998-04-29
1999-12-14
White, Everett
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
514361, 514364, 548100, A61K 31535
Patent
active
060018291
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to novel fluoropropenyl heterocycles, to processes for their preparation and to their use for controlling animal pests, in particular insects, arachnids and nematodes, encountered in agriculture, in forests, in the protection of stored products and of materials, and in the hygiene sector.
It is already known that certain fluorobutenyl compounds have nematicidal activity (cf. for example WO 88/00183). However, the efficacy and the activity spectrum of these compounds, in particular at low application rates and concentrations, are not always entirely satisfactory.
This invention, accordingly, provides novel compounds of the formula (I) ##STR1## and R represents respectively optionally substituted alkyl, aryl, aralkyl or hetaryl.
Furthermore, it has been found that the compounds of the formula (I) are obtained when ##STR2## in which R is as defined above presence of a base, and the resulting intermediates of the formula (IV) ##STR3## in which R and X are each as defined above of a base, compounds of the formula (VI) cyclized in the presence of a diluent and, if appropriate, in the presence of a dehydrating agent.
Finally, it has been found that the novel compounds of the formula (I) have pronounced biological properties and are suitable especially for controlling animal pests, in particular insects, arachnids and nematodes, encountered in agriculture, in forests, in the protection of stored products and of materials, and in the hygiene sector.
The formula (I) provides a general definition of the compounds according to the invention.
Preferred substituents or ranges of the radicals listed in the formulae mentioned hereinabove and hereinbelow are illustrated below. ##STR4## R preferably represents C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -halogenylalkyl, C.sub.1 -C.sub.8 -alkoxy-C.sub.1 -C8-alkyl, C.sub.1 -C.sub.8 -alkylthio-C.sub.1 -C.sub.8 -alkyl, phenoxy-C.sub.1 -C.sub.4 -alkyl which is optionally halogen-, C.sub.1 -C.sub.6 -alkyl-, C.sub.1 -C.sub.6 -alkoxy-, C.sub.1 -C.sub.6 -halogenoalkyl- or C.sub.1 -C.sub.6 -halogenoalkoxy-substituted in the phenyl moiety, C.sub.1 -C.sub.6 -alkoxy-, C.sub.1 -C.sub.6 -alkylthio-, C.sub.1 -C.sub.6 -halogenoalkyl-, C.sub.1-C.sub.8 -alkoxycarbonyl-, aminocarbonyl-, C.sub.1 -C.sub.6 -alkylaminocarbonyl-, di-C.sub.1 -C.sub.6 -alkylaminocarbonyl-, nitro-, cyano- or SCN-substituted phenyl, halogen-, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -halogenoalkyl-, C.sub.1 -C.sub.4 -alkoxy- or C.sub.1 -C.sub.4 -alkylthio-substituted in the phenyl moiety, or C.sub.1 -C.sub.6 -alkyl-, C.sub.1 -C.sub.6 -halogenoalkyl- or phenyl- (which is optionally substituted by halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -halogenoalkyl or C.sub.1 -C.sub.4 -halogenoalkoxy) substituted 5- or 6-membered heteraryl having one or two hetero atoms from the group consisting of oxygen, sulphur and nitrogen. ##STR5## R particularly preferably represents C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.3 -halogenoalkyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkylthio-C.sub.1 -C.sub.4 -alkyl, phenoxy-C.sub.1 -C.sub.2 -alkyl which is optionally fluorine-, chlorine-, C.sub.1 -C.sub.4 -alkyl-, C.sub.1 -C.sub.4 -alkoxy-, C.sub.1 -C.sub.3 -halogenoalkyl- or C.sub.1 -C.sub.3 -halogenoalkoxy-substituted in the phenyl moiety, -C.sub.4 -alkyl-, C.sub.1 -C.sub.4 -alkoxy-, C.sub.1 -C.sub.4 -alkylthio-, nitro- or cyano-substituted phenyl, optionally fluorine-, chlorine-, C.sub.1 -C.sub.4 -alkyl-, or C.sub.1 -C.sub.2 -halogenoalkyl-substituted in the phenyl moiety, or optionally fluorine-, chlorine-, C.sub.1 -C.sub.4 -alkyl-, C.sub.1 -C.sub.2 -halogenoalkyl- or phenyl- (which is optionally substituted by halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.2 -halogenoalkyl, C.sub.1 -C.sub.2 -alkoxy or C.sub.1 -C.sub.2 -halogenoalkoxy) substituted furanyl, thienyl or pyridyl. ##STR6## R very particularly preferably represents C.sub.1 -C.sub.3 -alkyl, chloromethyl, trifluoromethyl, C.sub.1 -C.sub.4 -alkoxymethyl, C.sub.1 -C.sub.4 -alkylthiomethyl, ph
REFERENCES:
patent: 4861367 (1989-08-01), Nyfeler et al.
patent: 4952580 (1990-08-01), Martinet et al.
Ando et al., "3-(3,3-Dihal-2-propenyl) . . . and photostability," Journal of Agricultural and Food Chemistry, vol. 31, No. 2 (1983) pp. 250-253.
Andersch Wolfram
Erdelen Christoph
Kraatz Udo
Kramer Wolfgang
Mencke Norbert
Bayer Aktiengesellschaft
White Everett
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