Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1998-05-22
1999-12-21
Richter, Johann
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514540, 514613, 548530, 548540, 560 41, 560 51, 560174, A61K 3124, C07C 6974, C07C 69716, C07D20909
Patent
active
060049928
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to novel fluorobutenyl aminocarboxylates, 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 fluoroalkenyl compounds have insecticidal, acaricidal and nematicidal activity (cf. for example WO 92/15 555, U.S. Pat. No. 4,952,590, U.S. Pat. No. 4,950,666, U.S. Pat. No. 3,914,251). However, the efficacy and the activity spectrum of these compounds, in particular at low application rates and concentrations, is not always entirely satisfactory.
This invention, accordingly, provides novel fluorobutenyl aminocarboxylates of the formula (I) ##STR3## (b) R.sup.3 --A--CO--NR.sup.4 --CR.sup.5 R.sup.6 -- or ##STR4## in which R.sup.1 represents respectively optionally substituted alkyl, aryl or hetaryl, aryl, halogenoalkoxy, alkylthio, halogenoalkylthio or respectively optionally substituted aralkyloxy or aryl, hydrogen, alkyl or respectively optionally substituted aralkyl or aryl, or and
Taking into account the various meanings of group R, the following structures are obtained: ##STR5## --CX.dbd.CF.sub.2 (Ib) ##STR6## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, A and X are each as defined above.
The compounds of the formula (I) can be present as geometric and/or optical isomers, or isomer mixtures of varying compositions, depending inter alia on the nature of the substituents. The invention provides both the pure isomers and the isomer mixtures.
Furthermore, it has been found that, formula (II) ##STR7## in which R.sup.1 and R.sup.2 are each as defined in claim 1 base, reactive reagent, or ##STR8## in which R.sup.3, R.sup.5 and R.sup.6 are each as defined above base, and the formula (VI) ##STR9## in which R.sup.3 is as defined above reactive reagent.
Finally, it has been found that the novel fluorobutenyl aminocarboxylates 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 fluorobutenyl aminocarboxylates according to the invention.
Preferred substituents or ranges of the radicals listed in the formulae mentioned hereinabove and hereinbelow are illustrated below: ##STR10## (b) R.sup.3 --A--CO--NR.sup.4 --CR.sup.5 R.sup.6 -- or ##STR11## R.sup.1 preferably represents C.sub.1 -C.sub.6 -alkyl or phenyl which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -halogenoalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.4 -halogenoalkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.4 -halogenoalkylthio, cyano, nitro and SCN, or preferably represents thienyl, furanyl or pyridyl, each of which is optionally mono- or disubstituted by identical or different substituents from the group consisting of halogen and C.sub.1 -C.sub.4 -alkyl. -C.sub.6 -halogenoalkyl, or preferably represents phenyl which is optionally mono- to trisubstituted by identical or different substituents from the group consisting of halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.4 -halogenoalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.4 -halogenoalkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.4 -halogenoalkylthio, cyano, nitro and SCN. -C.sub.4 -halogenoalkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.4 -halogenoalkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.4 -halogenoalkylthio, benzyloxy which is optionally mono- to trisubstituted in the phenyl moiety by identical or different substituents from the group consisting of halogen and C.sub.1 -C.sub.6 -alkyl, or phenyl which is optionally mono- to trisubstituted by identical or different substituents from the group co
REFERENCES:
Chemical Abstract 119, 94 942 "Preparation of Fluoroalkenyl group-containing compounds as pesticides" Sep. 16, 1992.
Houben-Weyl, Methoden der organischen Chemie, Georg Thieme Verlag, Stuttgart, 1974, vol. XV/1, p. 315 f.
Houben-Weyl, Methoden der organischen Chemie, Georg Thieme Verlag, Stuttgart, 1974, vol. XV/1, p. 46 ff.
Andersch Wolfram
Kraatz Udo
Mencke Norbert
Turberg Andreas
Bayer Aktiengesellschaft
Oswecki Jane C.
Richter Johann
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