Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Patent
1995-06-06
1996-10-15
Morris, Patricia L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
544 54, A01N 4386, C07D27906, C07D41712
Patent
active
055654509
DESCRIPTION:
BRIEF SUMMARY
The invention relates to new 5-aryl-1,3-thiazine derivatives, to processes for their preparation and to their use as pesticides.
Certain 5-phenyl-1,3-thiazine derivatives which are unsubstituted in the phenyl ring have already been disclosed (cf. E. Ziegler and E. Steiner, Monatsh. 95, 147 (1964), R. Ketcham, T. Kappe and E. Ziegler, J. Heterocycl. Chem. 10, 223 (1973)), but a possible use as pesticides is not mentioned for these, compounds.
There have now been found the new substituted 5-aryl-1,3-thiazine derivatives of the general formula (I) ##STR2## in which A represents an optionally substituted radical from the series consisting of alkyl, cycloalkyl, alkenyl, alkinyl, arylalkyl, aryl, hetarylalkyl and hetaryl, or represents an optionally substituted radical from the series consisting of alkoxy, cycloalkoxy, alkenyloxy, alkinyloxy, arylalkenloxy, aryloxy, hetarylalkyloxy and hetaryloxy or represents an optionally substituted radical from the series consisting of alkylthio, cycloalkylthio, alkenylthio, alkinylthio, arylalkylthio, arylthio, hetarylalkylthio and hetarylthio, or represents the groups ##STR3## and CSNR.sup.1 R.sup.2 in which R.sup.1 and R.sup.2 independently of one another represent optionally substituted radicals from the series consisting of alkyl, alkenyl, arylalkyl, aryl, hetarylalkyl and hetaryl or group which can be interrupted by one or more hetero atoms; --COR.sup.3, ##STR4## in which represents optionally substituted radicals from the series consisting of alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl, alkylthioalkyl, cycloalkyl which is optionally interrupted by one or more hetero atoms and optionally substituted, arylalkyl, aryl, hetarylalkyl, hetaryl, aryloxyalkyl and hetaryloxyalkyl; consisting of alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl, aryl and arylalkyl; optionally substituted radicals from the series consisting of alkyl, alkoxy, alkenoxy, alkylthio, alkylamino, dialkylamino, alkenylthio, alkinylthio, cycloalkylthio, aryl, aryloxy and arylthio; optionally substituted radicals from the series consisting of alkyl, alkenyl, cycloalkyl, alkoxyalkyl, aryl or arylalkyl, or together form an optionally substituted alkylene group which can be interrupted by one or more hetero atoms or hetero groups;
Depending on the substituents, the compounds of the general formula (I) can exist as geometric and/or optical isomers or variously composed mixtures of isomers. The invention claimed extends to the pure isomers as well as the isomer mixtures, their preparation, their use, and compositions containing them. For the sake of simplicity, however, the following text will always mention compounds of the formula (I), even though this is to be understood as meaning the pure compounds and, if appropriate, also mixtures containing various proportions of isomeric compounds.
Furthermore, it has been found that the new compounds of the general formula (I) display a very potent activity as pesticides, preferably as insecticides, acaricides, nematicides and herbicides, as well as ecto- and endoparasiticides.
Furthermore, it has been found that the new 5-aryl-1,3-thiazine derivatives of the general formula (I) are obtained when, the general formula (II) ##STR5## in which A has the abovementioned meaning ##STR6## in which X, Y, Z and n have the abovementioned meanings and acceptor; and represents --COR.sup.3, can be obtained by variant a)) are reacted ##STR7## in which R.sup.3 has the abovementioned meaning and ##STR8## in which R.sup.3 has the abovementioned meaning, presence of an acid-binding agent; and represents --C(L)--MR.sup.4 where L denotes oxygen and M and R.sup.4 have the abovementioned meaning, can be obtained by variant a)) ##STR9## in which R.sup.4 and M have the abovementioned meanings, presence of an acid-binding agent; and represents --C(L)--MR.sup.4 where L denotes sulphur and M and R.sup.4 have the abovementioned meaning, can be obtained by variant a)), are reacted ##STR10## in which R.sup.4 and M have the abovementioned meanings, presence of an acid-binding agent, or halides of the
REFERENCES:
Ketcham et al, "Synthesis of Heterocycles. etc", J. Heterocy. Chem (1973), 10(2), 223-224.
Ziegler et al, "Synthesis of heterocycles. etc" CA60:15863d (1964).
E. Ziegler, et al., Monatshefte F ur Chemie, vol. 95, No. 1, pp. 147-155, (1964).
Dollinger Markus
Erdelen Christoph
Fischer Reiner
L urssen Klaus
Lieb Folker
Bayer Aktiengesellschaft
Morris Patricia L.
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