1,3,4-oxadiazine derivatives and their use as pesticides

Details 1,3,4-oxadiazine derivatives and their use as pesticides 1,3,4-oxadiazine derivatives and their use as pesticides

1998-09-18

2000-10-03

Shah, Mukund J.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

504130, 544 66, 544 68, 5142288, C07D27304, C07D49804, A01N 4388, C07C28102

Patent

active

061273643

DESCRIPTION:

BRIEF SUMMARY
The invention relates to novel (1,3,4)-oxadiazine derivatives, to a plurality of processes and intermediates for their preparation and to their use as pesticides, in particular as anthelmintics, insecticides, acaricides and nematicides.
Only a single representative of the 2,5-dichalkogeno-(1,3,4)-oxadiazinanes, 6,6-diphenyl-(1,3,4)-oxadiazinane-2,5-dione is hitherto known (Liebigs Ann. Chem. 1981, 1433).
This invention, accordingly, provides novel (1,3,4)-oxadiazine derivatives of the formula (I) ##STR1## in which R.sup.1 and R.sup.2 independently of one another each represent hydrogen, respectively optionally halogen-substituted alkyl, hydroxyalkyl, alkanoyloxyalkyl, alkoxyalkyl, arylalkoxyalkyl, mercaptoalkyl, alkylthioalkyl, alkylsulphinylalkyl, alkylsulphonylalkyl, carboxyalkyl, alkoxycarbonylalkyl, aryloxycarbonylalkyl, arylalkyloxycarbonylalkyl, carbamoylalkyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkoxycarbonylaminoalkyl, alkylcarbonyl, cycloalkylcarbonyl or represent respectively optionally substituted cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, arylcarbonyl, heterocyclylalkyl, hetaryl or hetarylalkyl or substituted heterocyclic ring, respectively optionally halogen-substituted alkyl, alkenyl, hydroxyalkyl, alkanoyloxyalkyl, alkoxyalkyl, arylalkoxyalkyl, mercaptoalkyl, alkylthioalkyl, alkylsulphinylalkyl, alkylsulphonylalkyl, alkoxycarbonylalkyl, aryloxycarbonylalkyl, arylalkyloxycarbonylalkyl, carbamoylalkyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkylcarbonyl, cycloalkylcarbonyl or represent respectively optionally substituted cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, hetaryl or hetarylalkyl or ##STR2##
in which respectively optionally halogen-substituted alkyl, alkenyl, hydroxyalkyl, alkanoyloxyalkyl, alkoxyalkyl, arylalkoxyalkyl, mercaptoalkyl, alkylthioalkyl, alkylsulphinylalkyl, alkylsulphonylalkyl, alkoxycarbonylalkyl, aryloxycarbonylalkyl, aminoalkyl, alkylaminoalkyl, dialkylaminoalkyl, alkylcarbonyl or represent respectively optionally substituted cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, hetaryl or hetarylalkyl and sulphur,
Depending inter alia on the nature of the substituents, the compounds of the formula (I) may be present as geometric and/or optical isomers or mixtures of isomers, in varying compositions, which can, if appropriate, be separated in a customary manner. The present invention provides both the pure isomers and the isomer mixtures, their preparation and their use and compositions comprising them. Hereinbelow, for the sake of simplicity, reference is however always made to compounds of the formula (I) although this includes both the pure isomers and, if appropriate, also mixtures having varying proportions of isomeric compounds.
Furthermore, it has been found that the novel compounds of the formula (I) are obtained by one of the processes described below. ##STR3##
in which
can be prepared by reacting carbazates of the formula (II) ##STR4##
in which
in the presence of a reaction auxiliary and a diluent and, if appropriate, in the presence of a base. ##STR5##
in which hydrogen,
can be prepared by reacting
(1,3,4)-oxadiazine derivatives of the formula (I-c) ##STR6##
in which
with compounds of the formula (III)
in which
if appropriate in the presence of a diluent and, if appropriate, in the presence of a reaction auxiliary. ##STR7##
in which ##STR8##
in which optionally substituted alkyl or aryl, or ##STR9##
in which
can be prepared by reacting
(1,3,4)-oxadiazine derivatives of the formula (I-c) ##STR10##
in which
with ketones or aldehydes of the formula (IV)
in which
if appropriate in the presence of a diluent and, if appropriate, in the presence of a reaction auxiliary, and subsequently, if appropriate, eliminating water. ##STR11##
in which hydrogen,
can be prepared by reacting (1,3,4)-oxadiazine derivatives of the formula (I-f) ##STR12##
in which
with compounds of the formula (V)
in which
if appropriate in the presence of a diluent and, if appropriate, in the presence of a reaction auxiliary. ##STR13##
in which and hydrogen,
can be prepared by

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