Phenylcarbamates, methods for preparing them and agents containi

Details Phenylcarbamates, methods for preparing them and agents containi Phenylcarbamates, methods for preparing them and agents containi

1998-11-05

2000-10-10

Geist, Gary

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Ester doai

514538, 514542, 560 9, 560 29, A01N 3752, A01N 3712, A01N 3718, C07C27126

Patent

active

061302473

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to phenylcarbamates of the formula ##STR1## where X is a direct bond, O or NR.sup.a ; C.sub.3 -C.sub.6 -alkynyl; -haloalkyl; and -C.sub.6 -alkynyl, where these groups may be partially or completely halogenated and/or may carry from one to three of the following radicals: -alkylthio, C.sub.1 -C.sub.6 -haloalkylthio, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.1 -C.sub.6 -alkylsulfoxyl, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, radicals in turn may be partially or completely halogenated and/or may carry from one to three of the following groups: cyano, nitro, amino, aminocarbonyl, aminothiocarbonyl, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkylcarbonyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -haloalkylthio, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.1 -C.sub.6 -alkylsulfoxyl, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, C.sub.1 -C.sub.6 -alkylaminocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminocarbonyl, C.sub.2 -C.sub.6 -alkenyloxy and phenyl; the following radicals: -alkylthio, C.sub.1 -C.sub.6 -haloalkylthio, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.1 -C.sub.6 -alkylsulfoxyl, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, radicals in turn may be partially or completely halogenated and/or may carry from one to three of the following groups: cyano, nitro, amino, aminocarbonyl, aminothiocarbonyl, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkylcarbonyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkoxycarbonyl, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -haloalkylthio, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.1 -C.sub.6 -alkylsulfoxyl, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, C.sub.1 -C.sub.6 -alkylaminocarbonyl, di-C.sub.1 -C.sub.6 -alkylaminocarbonyl, C.sub.2 -C.sub.6 -alkenyloxy and phenyl; completely halogenated and/or may carry from one to three of the following radicals: -alkoxy, C.sub.1 -C.sub.6 -haloalkoxy, C.sub.1 -C.sub.6 -alkylthio, C.sub.1 -C.sub.6 -haloalkylthio, C.sub.1 -C.sub.6 -alkylsulfonyl, C.sub.1 -C.sub.6 -alkylsulfoxyl, C.sub.1 -C.sub.6 -alkylamino, di-C.sub.1 -C.sub.6 -alkylamino, -C.sub.6 -alkynyl, where these groups may be partially or completely halogenated and/or may carry from one to three of the following radicals: may be partially and/or completely halogenated and/or may carry from one to three C.sub.1 -C.sub.4 -alkyl groups; and additionally hydrogen; and alkynyl, alkylcarbonyl or alkoxycarbonyl.
The present invention furthermore relates to processes for the preparation of these compounds and to agents which contain them and are suitable for controlling animal pests and harmful fungi.
The literature discloses anilides for controlling animal pests and harmful fungi (WO-A93/15,046; German Application No. P 44 41 674.1).
It is an object of the present invention to provide compounds having improved activity compared with the above.
We have found that this object is achieved by the phenylcarmamates I defined at the outset.
We have also found processes for their preparation and agents which contain them and are suitable for controlling animal pests and harmful fungi.
The compounds I are obtainable in various ways by processes known per se in the literature. In the synthesis of the compounds I, it is in principle unimportant whether the group N(OR.sup.5)--COXR.sup.4 or the group --CH.sub.2 ON.dbd.CR.sup.1 --C(ZR.sup.2).dbd.NOR.sup.3 is synthesized first. The various methods for synthesizing the N(OR.sup.5)--COXR.sup.4 group (denoted in some of the formulae below by the symbol # for short) are disclosed, for example, in the literature cited at the outset.
The group --CH.sub.2 ON.dbd.CR.sup.1 --C(ZR.sup.2).dbd.NOR.sup.3 is synthesized in general by reacting a benzyl derivative of the formula II with a hydroxyimine of the formula III. ##STR2##
In the formula II, L.sup.1 is a nucleophilically substitutable leaving g

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