Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Nitrogen containing other than solely as a nitrogen in an...
Patent
1998-02-09
1999-07-27
Rotman, Alan L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Nitrogen containing other than solely as a nitrogen in an...
564 78, 564 84, 564155, 564204, 514602, 514616, A61K 3118, C07C32748
Patent
active
059291184
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to novel fluorobutenic acid hydrazides, 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 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. 4,952,580, U.S. Pat. No. 4,950,666, U.S. Pat. No. 3,914,251). However, the activity 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 fluorobutenic acid hydrazides of the formula (I) ##STR2## in which Y represents C.dbd.O, C.dbd.S or SO.sub.2, cycloalkyl, alkenyl, alkenyloxy, alkoxy, cycloalkyloxy, alkylthio or respectively optionally substituted aryl, aralkyl, aralkyloxy or hetaryl.
Depending on the nature of the substituents, the compounds of the formula (I) may be present as geometrical and/or optical isomers or as mixtures of isomers in varying composition. The present invention provides both the pure isomers and the isomer mixtures.
Furthermore, it has been found that the fluorobutenic acid hydrazides of the formula (I) are obtained when the formula (III) ##STR3## in which R.sup.1 is as defined above, presence of a base, ##STR4## in which R.sup.1 is as defined above are reacted with acyl chlorides of the formula (V) presence of a base.
Finally, it has been found that the novel fluorobutenic acid hydrazides of the formula (I) have very pronounced biological properties and are particularly suitable for controlling animal pests, in particular insects, arachnids and nematodes, encountered in agriculture, in forests, in the protection of stored products and materials, and in the hygiene sector.
The formula (I) provides a general definition of the fluorobutenic acid hydrazides according to the invention.
Preferred substituents or ranges of the radicals listed in the formulae mentioned above and below are illustrated below: -halogenoalkyl, C.sub.1 -C.sub.6 -alkoxy-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkylthio-C.sub.1 -C.sub.6 -alkyl, C.sub.3 -C.sub.10 -cycloalkyl, C.sub.2 -C.sub.8 -alkenyl, C.sub.2 -C.sub.8 -alkenyloxy, C.sub.1 -C.sub.20 -alkoxy, C.sub.3 -C.sub.10 -cycloalkyloxy, C.sub.1 -C.sub.20 -alkylthio, respectively optionally halogen-, nitro-, cyano-, amino-, hydroxyl-, C.sub.1 -C.sub.6 -alkyl-, C.sub.1 -C.sub.6 -alkoxy- or C.sub.1 -C.sub.6 -alkylthio-substituted phenyl, phenyl-C.sub.1 -C.sub.4 -alkyl or phenyl-C.sub.1 -C.sub.4 -alkyloxy or optionally halogen- or C.sub.1 -C.sub.6 -alkyl-substituted 5- or 6-membered hetaryl, having one or two hetero atoms from the group oxygen, sulphur and nitrogen. -C.sub.6 -cycloalkyl, C.sub.3 -C.sub.8 -alkenyl, C.sub.3 -C.sub.8 -alkenyloxy, C.sub.1 -C.sub.6 -alkoxy, C.sub.3 -C.sub.6 -cycloalkyloxy, C.sub.1 -C.sub.6 -alkylthio, respectively optionally fluorine-, chlorine-, bromine-, hydroxyl-, C.sub.1 -C.sub.4 -alkyl- or C.sub.1 -C.sub.4 -alkoxy-substituted phenyl, phenyl-C.sub.1 -C.sub.2 -alkyl or phenyl-C.sub.1 -C.sub.2 -alkyloxy or respectively optionally C.sub.1 -C.sub.4 -alkyl-substituted furanyl, thienyl or pyridyl.
The abovementioned general or preferred radical definitions or illustrations apply to the end products and, correspondingly, to the starting materials and intermediates. These radical definitions can be combined with each other as desired, i.e. including combinations between the respective preferred ranges.
Preference according to the invention is given to the compounds of the formula (I) which contain a combination of the definitions given above as being preferred (preferable).
Particular preference according to the invention is given to the compounds of the formula (I) which contain a combination of the definitions given above as being particularly preferred.
In the radical definitions given above and below, hydrocarbon radicals such as alk
REFERENCES:
patent: 4950666 (1990-08-01), Peake et al.
patent: 5389680 (1995-02-01), Ruminski
patent: 5514717 (1996-05-01), Phillion et al.
Andersch Wolfram
Kraatz Udo
Kramer Wolfgang
Mencke Norbert
Turberg Andreas
Aulakh Charanjit S.
Bayer Aktiengesellschaft
Rotman Alan L.
LandOfFree
Fluorobutenic acid hydrazides does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Fluorobutenic acid hydrazides, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Fluorobutenic acid hydrazides will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-879218