Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1996-07-11
1998-08-25
Daus, Donald G.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
548216, 5462714, 514340, 549330, C07D49810
Patent
active
057983763
DESCRIPTION:
BRIEF SUMMARY
The invention relates to new azatrioxaspiroalkenes, to a plurality of processes for their preparation, and to their use for combating animal pests.
It has already been disclosed that certain oxazoline derivatives have insecticidal and acaricidal properties (cf., for example, EP-A 0345775 and EP-A 0432661).
However, the activity of these prior-art compounds is not entirely satisfactory in all fields of application, in particular at low application rates and concentrations.
The new azatrioxaspiroalkenes of the formula (I) ##STR2## in which Ar.sup.1 and Ar.sup.2 are identical or different and independently of one another in each case represent optionally substituted aryl,
Furthermore, it has been found that azatrioxaspiroalkenes of the formula (I) are obtained by a process which comprises ##STR3## in which Ar.sup.2 has the abovementioned meaning, and carboxylic acids of the formula (III) appropriate in the presence of a diluent, or ##STR4## in which Ar.sup.1 and Ar.sup.2 have the abovementioned meanings, with a dehydrating agent, if appropriate in the presence of a diluent, or ##STR5## in which Ar.sup.1 and Ar.sup.2 have the abovementioned meanings and ##STR6## in which Ar.sup.1 and Ar.sup.2 have the abovementioned meanings, with a base, if appropriate in the presence of a diluent.
Furthermore, it has been found that azatrioxaspiroalkenes of the formula (I) are highly suitable for combating animal pests. They are distinguished, in particular, by a high activity against arthropods and nematodes. The azatrioxaspiroalkenes of the formula (I) can be employed as a stereoisomer mixture as well as in the form of their pure E or Z isomers.
Surprisingly, the azatrioxaspiroalkenes of the formula (I) according to the invention show a considerably better activity against animal pests than the prior-art compounds of the most similar constitution.
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 in the following text. to pentasubstituted by identical or different substituents from the series consisting of halogen, cyano, nitro, hydroxyl, 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 or C.sub.1 -C.sub.6 -halogenoalkylthio, to pentasubstituted by identical or different substituents from the series consisting of halogen, cyano, nitro, hydroxyl, C.sub.1 -.sub.18 -alkyl, C.sub.1 -C.sub.8 -halogenoalkyl, C.sub.1 -C.sub.8 -alkoxy-C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.18 -alkoxy (in which individual methylene groups are optionally replaced by oxygen atoms), C.sub.1 -C.sub.8 -halogenoalkoxy, C.sub.1 -C.sub.18 -alkylthio, C.sub.1 -C.sub.8 -halogenoalkylthio, C.sub.1 -C.sub.8 -alkyl-carbonyl, C.sub.1 -C.sub.8 -halogenoalkyl-carbonyl, C.sub.1 -C.sub.8 -alkoxy-carbonyl, C.sub.1 -C.sub.8 -halogenoalkoxy-carbonyl, C.sub.1 -C.sub.3 -alkylenedioxy, C.sub.1 -C.sub.3 -halogenoalkylenedioxy, or cyclohexyl, cyclohexylmethyl or cyclohexyloxy, each of which is optionally substituted by C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, cyclohexyl or phenyl, or pyridyloxy which is optionally monosubstituted to trisubstituted by identical or different substituents from the series consisting of halogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -halogenoalkyl, or phenyl, benzyl, benzoyl, phenoxy, phenylthio, benzyloxy or benzylthio, each of which is optionally monosubstituted to tetrasubstituted by identical or different substituents from the series consisting of halogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -halogenoalkyl, C.sub.1 -C.sub.6 -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 or C.sub.1 -C.sub.6 -halogenoalkylthio.
The hydrocarbon radicals, such as alkyl, which are mentioned above in the definition of the compounds according to the invention are, as far as thi
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Erdelen Christoph
Fischer Reiner
Mencke Norbert
Turberg Andreas
Wachendorff-Neumann Ulrike
Bayer Aktiengesellschaft
Daus Donald G.
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