1,3,4-oxadiazolin-2-ones and their use as pesticides

Details 1,3,4-oxadiazolin-2-ones and their use as pesticides 1,3,4-oxadiazolin-2-ones and their use as pesticides

1998-02-20

2000-01-11

Higel, Floyd D.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

514364, C07D27113, A01N 43824

Patent

active

060138041

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to novel 1,3,4-oxadiazolin-2-ones, to processes for their preparation and to their use for controlling animal pests.
It is already known that certain substituted 1,3,4-oxa(thia)diazolin-2-ones have insecticidal and acaricidal properties (cf. EP-A 0 270 061). However, the efficacy and/or duration of action of these prior art compounds, in particular at low application rates and concentrations, is not entirely satisfactory in all areas of use.
This invention, accordingly, provides novel 1,3,4-oxadiazolin-2-ones of the formula (I) ##STR2## in which Ar.sup.1 represents optionally substituted phenyl and
Furthermore, it has been found that 1,3,4-oxadiazolin-2-ones of the formula (I) are obtained when ##STR3## in which Ar.sup.1 and Ar.sup.2 are each as defined above appropriate, in the presence of a base, ##STR4## in which Ar.sup.1 is as defined above and in the presence of a diluent.
Furthermore, it has been found that the novel 1,3,4-oxadiazolin-2-ones of the formula (I) are highly suitable for controlling animal pests. In particular, they have high activity against arthropods.
Formula (I) provides a general definition of the 1,3,4-oxadiazolin-2-ones according to the invention.
Preferred substituents or ranges of the radicals listed in the formulae mentioned hereinabove and hereinbelow are given below. pentasubstituted by identical or different substituents from the group consisting of halogen, C.sub.1 -C.sub.6 -alkyl, 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.6 -halogenoalkoxy, C.sub.1 -C.sub.6 -halogenoalkylthio, nitro and cyano. ##STR5## in which R represents phenyl which is optionally mono- to pentasubstituted by identical or different substituents from the group consisting of CHO, cyano, halogen, C.sub.1 C.sub.12 -alkyl, C.sub.1 -C.sub.4 -halogenoalkyl, C.sub.1 -C.sub.12 -alkoxy, C.sub.1 -C.sub.6 -halogenoalkoxy, C.sub.1 -C.sub.6 -alkoxy-C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy-ethyleneoxy, C.sub.1 -C.sub.6 -alkylthio and C.sub.1 -C.sub.6 -halogenoalkylthio. mono- to trisubstituted by identical or different substituents from the group consisting of 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.2 -alkyl which is mono- to pentasubstituted by identical or different substituents from the group consisting of fluorine and chlorine, C.sub.1 -C.sub.4 -alkoxy which is mono- to pentasubstituted by identical or different substituents from the group consisting of fluorine and chlorine, SCF.sub.3, SCHF.sub.2, nitro and cyano. ##STR6## in which R represents phenyl which is optionally mono- to pentasubstituted by identical or different substituents from the group consisting of CHO, cyano, fluorine, chlorine, bromine, C.sub.1 -C.sub.12 -alkyl, C.sub.1 -C.sub.4 -alkyl which is mono- to hexasubstituted by identical or different substituents from the group consisting of fluorine and chlorine, C.sub.1 -C.sub.12 -alkoxy, C.sub.1 -C.sub.4 -alkoxy which is mono- to hexasubstituted by identical or different substituents from the group consisting of fluorine and chlorine, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy-ethyleneoxy, C.sub.1 -C.sub.4 -alkylthio and C.sub.1 -C.sub.4 -alkylthio which is mono- to hexasubstituted by identical or different substituents from the group consisting of fluorine and chlorine. trisubstituted by identical or different substituents from the group consisting of fluorine and chlorine. ##STR7## in which R represents phenyl which is optionally mono- to pentasubstituted by identical or different substituents from the group consisting of CHO, cyano, fluorine, chlorine, bromine, C.sub.1 -C.sub.12 -alkyl, C.sub.1 -C.sub.4 -alkyl which is mono- to hexasubstituted by identical or different substituents from the group consisting of fluorine and chlorine, C.sub.1 -C.sub.12 -alkoxy, C.sub.1 -C.sub.4 -alkoxy which is mono- to hexasubstituted by identical or different substituents from the group consisting of

REFERENCES:
patent: 4246403 (1981-01-01), Prossel et al.
patent: 4259104 (1981-03-01), Edwards
patent: 4943583 (1990-07-01), Luthy, I
patent: 5418246 (1995-05-01), Bettarini et al.

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