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

2000-07-06

2002-01-29

Shah, Mukund J. (Department: 1624)

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

Organic compounds

Chalcogen in the nitrogen containing substituent

C544S066000

Reexamination Certificate

active

06342599

ABSTRACT:

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)
in which
R
1
and R
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
R
1
, R
2
and the two linking nitrogen atoms represent an optionally substituted heterocyclic ring,
R
3
and R
4
independently of one another each represent hydrogen, 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
R
3
and R
4
together represent alkylene or the radical (a)
in which
R
5
and R
6
independently of one another each represent hydrogen, 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
Q
1
and Q
2
independently of one another each represent oxygen or sulphur, except for 6,6-diphenyl-(1,3,4)-oxadiazinane-2,5-dione.
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.
A) (1,3,4)-Oxadiazine derivatives of the formula (I-a)
in which
R
1
to R
4
and Q
1
are each as defined above,
can be prepared by reacting carbazates of the formula (II)
in which
R
1
to R
4
and Q
1
are each as defined above,
in the presence of a reaction auxiliary and a diluent and, if appropriate, in the presence of a base.
B) (1,3,4)-Oxadiazine derivatives of the formula (I-b)
in which
R
1
to R
3
, Q
1
and Q
2
are each as defined above and
R
4-1
represents the same radicals as R
4
, with the exception of hydrogen,
can be prepared by reacting
(1,3,4)-oxadiazine derivatives of the formula (I-c)
in which
R
1
and R
2
have meanings other than hydrogen,
R
3
, Q
1
and Q
2
are each as defined above,
with compounds of the formula (III)
R
4-1
—E   (III),
in which
R
4-1
is as defined above and
E represents an electron-withdrawing leaving group,
if appropriate in the presence of a diluent and, if appropriate, in the presence of a reaction auxiliary.
C) (1,3,4)-Oxadiazine derivatives of the formula (I-d)
in which
R
1
to R
3
, Q
1
and Q
2
are each as defined above and
R
4-2
represents the radical (b)
in which
R
5
and R
6
independently of one another each represent hydrogen, optionally substituted alkyl or aryl, or
R
3
and R
4-2
together represent the radical (a)
in which
R
5
and R
6
are each as defined above,
can be prepared by reacting
(1,3,4)-oxadiazine derivatives of the formula (I-c)
in which
R
1
to R
3
, Q
1
and Q
2
are each as defined above with ketones or aldehydes of the formula (IV)
R
5
—CO—R
6
  (IV),
in which
R
5
and R
6
are each as defined above,
if appropriate in the presence of a diluent and, if appropriate, in the presence of a reaction auxiliary, and subsequently, if appropriate, eliminating water.
D) (1,3,4)-Oxadiazine derivatives of the formula (I-e)
in which
R
1-1
represents the same radicals as R
1
, with the exception of hydrogen,
R
2
to R
4
, Q
1
and Q
2
are each as defined above,
can be prepared by reacting (1,3,4)-oxadiazine derivatives of the formula (I-f)
in which
R
2
to R
4
, Q
1
and Q
2
are each as defined above,
with compounds of the formula (V)
R
1-1
—E   (V),
in which
R
1-1
is as defined above and
E represents an electron-withdrawing leaving group,
if appropriate in the presence of a diluent and, if appropriate, in the presence of a reaction auxiliary.
E) (1,3,4)-Oxadiazine derivatives of the formula (I-g)
in which
R
1
, R
3
, R
4
, Q
1
and Q
2
are each as defined above and
R
2-1
represents the same radicals as R
2
, with the exception of hydrogen,
can be prepared by reacting (1,3,4)-oxadiazine derivatives of the formula (I-h)
in which
R
1
, R
3
, R
4
, Q
1
and Q
2
are each as defined above,
with compounds of the formula (VI)
R
2-1
—E   (VI),
in which
R
2-1
is as defined above and
E represents an electron-withdrawing leaving group,
if appropriate in the presence of a diluent and, if appropriate, in the presence of a reaction auxiliary.
F) (1,3,4)-Oxadiazine derivatives of the formula (I)
in which
R
1
to R
4
, Q
1
and Q
2
are each as defined above,
can be prepared by reacting and cyclocondensing compounds of the formula (VII)
in which
R
1
to R
4
and Q
2
are each as defined above,
with compounds of the formula (VIII)
in which
Y
1
represents chlorine, trichloromethoxy, C
1
-C
4
-alkoxy, optionally substituted phenoxy, 1-imidazolyl or 1,2,4-triazolyl and
Y
2
represents chlorine, trichloromethoxy, 1-imidazolyl or 1,2,4-triazolyl,
Q
1
is as defined above,
if appropriate in the presence of a diluent and, if appropriate, in the presence of a reaction auxiliary.
G) (1,3,4)-Oxadiazine derivatives of the formula (I)
in which
R
1
to R
4
, Q
1
and Q
2
are each as defined above,
can be prepared by cyclocondensing compounds of the formula (IX)
in which
R
1
to R
4
, Q
1
, Q
2
and Y
1
are each as defined above,
if appropriate in the presence of a diluent and, if appropriate, in the presence of a reaction auxiliary.
H) (1,3,4)-Oxadiazine derivatives of the formula (I-i)
in which
R
1
to R
4
and Q
1
are each as defined above,
can be prepared by reacting (1,3,4)-oxadiazine derivatives of the formula (I-a)
in which
R
1
to R
4
and Q are each as defined above,
with a thionylating reagent, if appropriate in the presence of a diluent.
Furthermore, it has been found that the novel compounds of the formula (I) have very high activity as pesticides, preferably for controlling endoparasites in useful animals and for controlling insects, arachnids and nematodes encountered in agriculture, in forests, in the protection of stored products and materials and in the hygiene sector.
The formula (I) provides a general definition of the compounds according to the invention. Preferred substituents and ranges of the radicals listed in the formulae mentioned hereinabove and hereinbelow are illustra

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