4-Cyclohexylphenyl-oxazolines and their use for controlling anim

Details 4-Cyclohexylphenyl-oxazolines and their use for controlling anim 4-Cyclohexylphenyl-oxazolines and their use for controlling anim

1999-05-19

2000-01-18

Stockton, Laura L.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

548216, 548239, A01N 4376, C07D26310, C07D26314, C07D26352, C07D41310

Patent

active

060158239

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD OF THE INVENTION

The present invention relates to novel 4-cyclohexylphenyl-oxazolines, to a process for their preparation and to their use for controlling animal pests.


BACKGROUND OF THE INVENTION

It is already known that certain substituted biphenyl-oxazolines have insecticidal and acaricidal properties (cf. for example EP-A-0 432 661 or EP-A-0 696 584). However, the efficacy and/or the duration of action of these known compounds, in particular against certain organisms or at low application concentrations, is not entirely satisfactory in all areas of application.


DETAILED DESCRIPTION OF THE INVENTION

This invention, accordingly, provides novel 4-cyclohexylphenyl-oxazolines of the formula (I) ##STR2## in which X.sup.1 represents halogen, alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, amino, alkylamino or dialkylamino, hydrogen, halogen, alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, amino, alkylamino or dialkylamino, hydrogen, alkyl, alkenyl or optionally substituted benzyl, or they join with the hetero atoms to which they are attached and the carbon atom linking these to form an optionally substituted 5- or 6-membered ring; or .dbd.--NR.sup.6 R.sup.7, where optionally substituted benzyl; optionally substituted benzyl; and optionally substituted phenyl, phenylcarbonyl or benzyl or represents --CONR.sup.8 R.sup.9 or --SO.sub.2 NR.sup.8 R.sup.9 in which optionally substituted benzyl and optionally substituted phenyl, phenylcarbonyl or benzyl.
The 4-cyclohexylphenyl-oxazolines of the formula (1) can be present as optical and/or geometrical isomers, which depends, among other things, on the substituents. The present invention provides the isomer mixtures, and also the pure isomers.
Furthermore, it was found that the 4-cyclohexylphenyl-oxazolines of the formula (I) are obtained when ##STR3## in which X.sup.1, X.sup.2, X.sup.3, R.sup.1 and R.sup.2 are each as defined above, catalyst and if appropriate in the presence of a diluent; ##STR4## which are obtainable by the process (a) and in which X.sup.1, X.sup.2 and X.sup.3 are each as defined above, (IV) or compounds of the formula (V) ##STR5## in which R.sup.10 has the abovementioned meanings of R.sup.3 and/or R.sup.4 and chain, presence of a diluent; appropriate in the presence of a diluent and if appropriate in the presence of a base; it is also possible to alkylate the resulting derivatives where R.sup.5 =hydrogen subsequently; ##STR6## which are obtainable by process (a) and in which X.sup.1, X.sup.2 and X.sup.3 are each as defined above,
Furthermore, it was found that the novel 4-cyclohexylphenyl-oxazolines of the formula (I) are highly suitable for controlling animal pests, in particular insects, arachnids and nematodes, encountered in agriculture, in forestry, 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. -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, amino, C.sub.1 -C.sub.4 -alkylamino or di(C.sub.1 -C.sub.4 -alkyl)amino (in particular fluorine or chlorine, especially fluorine). represents hydrogen, fluorine, chlorine, bromine, 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, amino, C.sub.1 -C.sub.4 -alkylamino or di(C.sub.1 -C.sub.4 -alkyl)amino (where X.sup.3 in particular represents hydrogen and X.sup.2 in particular represents fluorine or chlorine, especially fluorine, in each case preferably in position 6). represent .dbd.N--OR.sup.5 or .dbd.N--NR.sup.6 R.sup.7. represents hydrogen, C.sub.1 -C.sub.4 -alkyl or benzyl which is optionally mono- to trisubstituted, preferably in the phenyl moiety, by identical or different substituents from the group consisting of halogen, C.sub.1

REFERENCES:
patent: 5141948 (1992-08-01), Miyamoto et al.
patent: 5354905 (1994-10-01), Sato et al.
patent: 5578625 (1996-11-01), Suzuki et al.

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