Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1997-06-06
1999-03-16
Daus, Donald G.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
544 66, 544 69, 514 63, 564 49, C07D27304, C07D41304, A01N 4388
Patent
active
058830910
DESCRIPTION:
BRIEF SUMMARY
The invention relates to new 1,3,4-oxadiazine derivatives, to a plurality of processes for their preparation, and to their use for combating animal pests.
It has already been disclosed that certain 1,3,4-oxadiazine derivatives, such as, for example, 2-(4-brormophenyl)-4-(2-fluoroeth-1-yl)-4H-5,6-dihydro-1,3,-4-oxadiazine have acaricidal properties (cf. Pesticide Biochemistry and Physiology 47, 1-7 (1993)).
However, the level and/or duration of action of these prior-art compounds is not entirely satisfactory in all fields of application, in particular when used against certain or,),anisms or at low rates.
There have now been found new 1,3,4-oxadiazine derivatives of the formula (I) ##STR2## in which Ar.sup.1 represents in each case optionally substituted aryl or hetaryl,
Furthermore, it has been found that the new 1,3,4-oxadiazine derivatives of the formula (I) are obtained when ethane derivatives of the formula (III) leaving group ##STR3## in which Ar.sup.1, Ar.sup.2, X and Y.sup.2 have the abovementioned meanings, in the presence of a base and if appropriate in the presence of a diluent; or ##STR4## in which Ar.sup.1 , Ar.sup.2 and X have the abovementioned meanings and of a diluent; or ##STR5## in which Ar.sup.1 has the abovementioned meanings meanings, and at least one of the indices m and n represents 1 or ##STR6## in which Ar.sup.1 has the abovementioned meanings and boronic acids of the formula (VIII)
Furthermore, it has been found that the new 1,3,4-oxadiazine derivatives of the formula (I) are highly suitable for combating animal pests. They are distinguished, in particular, by a potent activity against arthropods.
Surprisingly, the 1,3,4-oxadiazine derivatives of the formula (I) according to the invention display a considerably better activity against animal pests than the prior-art compounds of the most similar constitution, such as, for example, 2-(4-bromophenyl)-4-(2-fluoroethyl-1-yl)-4H-5,6-dihydro-1,3,4-oxadiazine.
Formula (I) provides a general definition of the compounds according to the invention.
Preferred substituents or ranges of the radicals mentioned in the formula given hereinabove and hereinbelow are illustrated in the following text. to pentasubstituted by identical or different substituents from the series 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 -haloogenoalkoxy, C.sub.1 -C.sub.6 -halogenoalkylthio, nitro and cyano, or represents 5- or 6-membered hetaryl having one or two identical or different hetero atoms from the series consisting of oxygen, sulphur and nitrogen which is optionally monosubstituted to trisubstituted by identical or different substituents from the series 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. to pentasubstituted by identical or different substituents from the series consisting of halogen, C.sub.1 -C.sub.18 -alkyl, C.sub.1 -C.sub.8 -alkoxy-C.sub.1 -C.sub.8 -alkyl, C.sub.1 -C.sub.8 -halogenoalkoxy, C.sub.1 -C.sub.4 -halogenoalkyl, C.sub.1 -C.sub.18 -alkoxy which is optionally interrupted by a further 1 to 3 oxygen atoms, C.sub.1 -C.sub.18 -alkylthio, C.sub.1 -C.sub.8 -halogenoalkylthio, cyclohexyl 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, pyridyloxy which is optionally monosubsutituted or disubstituted by identical or different substituents from the series consisting of halogen, C.sub.1 -C.sub.4 -alkyl and C.sub.1 -C.sub.4 -halogenoalkyl, and phenyl, benzyl, phenethyl, phenoxy, phenoxymethyl, phenylthio, benzyloxy, phenethyloxy, benzylthio or styryl, each of which is optionally monosubstituted to trisubstituted by identical or different substituents from the series consisting of C.sub.1 -C.sub.12 -alkyl, halogen, cyano, C.sub.1 -C.sub.4 -halogenoalkyl, C.sub.1 -C.sub.6 -alkoxy, C.su
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Kanellakopulos Johannes
Kleefeld Gerd
Wachendorff-Neumann Ulrike
Bayer Aktiengesellschaft
Daus Donald G.
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