Substituted biphenyl oxazolines

Details Substituted biphenyl oxazolines Substituted biphenyl oxazolines

1997-03-31

1998-09-15

McKane, Joseph

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

548237, A61K 3142, C07D26310

Patent

active

058078770

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/EP95/03787 filed Sep. 25, 1995.
The invention relates to new substituted biphenyloxazolines, to a plurality of processes and intermediates for their preparation, and to their use for combating animal pests.
It has been disclosed that certain substituted biphenyloxazolines, such as 2-(2,6-difluorophenyl)-4-(4'-trifluoromethylthiobiphenyl-4)-2-oxazoline, have an insecticidal and acaricidal activity (cf. WO 95/04726).
However, the level and/or duration of action of this known compound is not entirely satisfactory in all fields of application, in particular when directed against certain organisms or in the case of low use concentrations.
There have been found new substituted biphenyloxazolines of the formula (I) ##STR3## in which R.sup.1 represents C.sub.1 -C.sub.6 -halogenoalkylthio and form a halogen-substituted 5- or 6-membered heterocyclic ring, -alkoxy, and ##STR4##
Due to one or more chiral centers, the compounds of the formula (I) are generally obtained in the form of stereoisomer mixtures. They can be used both in the form of their diastereomer mixtures and in the form of the pure diastereomers or enantiomers.
Furthermore, it has been found that the new compounds of the formula (I) are obtained when ##STR5## in which R.sup.1, R.sup.2, X and m have the abovementioned meanings, catalyst and, if appropriate, in the presence of a diluent (process A).
Furthermore, it has been found that the new substituted biphenyloxazolines of the formula (I) are highly suitable for combating animal pests, in particular insects, arachnids and nematodes, which are encountered in agriculture, in forests, in the protection of stored products and materials, and in the hygiene sector.
Formula (I) provides a general definition of the compounds according to the invention.
Preferred substituents or ranges of the radicals mentioned in the formulae given hereinabove and hereinbelow are illustrated in the following text. atoms to which they are bonded form an oxygen-containing 5- or 6-membered ring which is monosubstituted or polysubstituted by fluorine and/or chlorine, SCF.sub.2 CF.sub.2 H, SCF.sub.2 Cl, SCF.sub.2 Br, SCF.sub.2 CH.sub.2 F, SCF.sub.2 CF.sub.3, SCF.sub.2 CHCl.sub.2, SCH.sub.2 CF.sub.2 CHF.sub.2, SCH.sub.2 CF.sub.2 CF.sub.3 or SCF.sub.2 CHFCF.sub.3, and together represent --OCF.sub.2 O--, --OCF.sub.2 CF.sub.2 O--, --OCF.sub.2 CFClO--, --OCF.sub.2 OCF.sub.2 or --OCF.sub.2 CF.sub.2 --.
Very particularly preferred compounds of the formula (I) are those in which R.sup.1 is bonded in the 4-position of the phenyl ring.
In each case, the compound of the formula ##STR6## is excepted.
The abovementioned definitions of radicals or illustrations, either in general or where preferred ranges are mentioned, can be combined as desired with each other, that is to say combinations between the ranges and preferred ranges in question are also possible. They apply to the end products and, analogously, to the precursors and intermediates.
Preferred compounds of the formula (I) according to the invention are those in which there exists a combination of the meanings mentioned above as preferred.
Particularly preferred compounds of the formula (I) according to the invention are those in which there exists a combination of the meanings mentioned above as particularly preferred.
If, for example, N-(1-(4-tetrafluoroethylthiobiphenyl-4)-2-chloro-ethyl-1)-2,6-difluorobenz amide is used as starting substance, the course of the process A according to the invention can be represented by the following equation: ##STR7##
Process A) for the preparation of the compounds of the formula (I) comprises cyclizing the compounds of the formula (II) in the presence of a base, if appropriate in the presence of a catalyst and, if appropriate, in the presence of a diluent.
Cyclization is preferably carried out in the presence of a diluent.
Suitable diluents are all inert organic solvents. If appropriate, they can be used in the form of a mixture with water. Substances which are preferably used are hydrocarbons, such as toluene, xyle

REFERENCES:
patent: 3901906 (1975-08-01), Kozlik

Affiliated with

Also associated with

Rating

Substituted biphenyl oxazolines 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 biphenyl oxazolines, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Substituted biphenyl oxazolines will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-87814