Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1993-10-12
1995-08-08
Tsang, Cecilia
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514357, 544319, 544334, 544335, 546338, A61K 31505, A61K 3144, C07D23902, C07D21356
Patent
active
054399106
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/GB92/00681, filed Apr. 14, 1992.
This invention relates to derivatives of propenoic acid useful as fungicides, to processes for preparing them, to compositions containing them, and to methods of using them to combat fungi, especially fungal infections of plants.
There are described in EP-A-0 370 629 fungicidal derivatives of propenoic acid which have the general formula (I) wherein A is hydrogen, halo, hydroxy, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkyl, C.sub.1-4 haloalkoxy, C.sub.1-4 alkylcarbonyl, C.sub.1-4 alkoxycarbonyl, phenoxy, nitro or cyano; R.sup.1 and R.sup.2, which may be the same or different, are hydrogen, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted heterocyclylalkyl, optionally substituted cycloalkylalkyl, optionally substituted aralkyl, optionally substituted heteroarylalkyl, optionally substituted aryloxyalkyl, optionally substituted heteroaryloxyalkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted alkoxy, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted aryloxy, optionally substituted heteroaryloxy, nitro, halo, cyano, --NR.sup.3 R.sup.4, --CO.sub.2 R.sup.3, --CONR.sup.3 R.sup.4, --COR.sup.3, --S(O).sub.n R.sup.3 wherein n is 0, 1 or 2, (CH.sub.2).sub.m PO(OR.sup.3).sub.2 wherein m is 0 or 1, or and R.sup.1 and R.sup.2 join to form a carbocyclic or heterocyclic ring system; and R.sup.3 and R.sup.4, which may be the same or different, are hydrogen, optionally substituted alkyl, optionally substituted aralkyl, optionally substituted alkenyl, optionally substituted alkynyl, optionally substituted aryl or optionally substituted heteroaryl. The compounds contain at least one carbon-carbon double bond and one carbon-nitrogen double bond and exist in the form of geometric isomers. The isomers which result from the unsymmetrically substituted double bonds of the propenoate group and the oxime ether are identified by the commonly used terms, "E" and "Z".
The present invention provides a compound of formula (I) wherein R.sup.1 is: alkoxy, C.sub.1-6 haloalkyl, C.sub.1-6 haloalkoxy, C.sub.1-4 alkoxy(C.sub.1-6)alkyl or C.sub.1-4 alkoxy(C.sub.1-6)alkoxy; C.sub.1-6 alkoxy, C.sub.1-6 alkylthio, C.sub.1-6 alkylsulphinyl, C.sub.1-6 haloalkoxy, C.sub.1-6 alkoxy(C.sub.1-6)alkyl, C.sub.1-6 alkoxy(C.sub.1-6)alkoxy, C.sub.1-4 alkoxy(C.sub.1-6)alkoxy(C.sub.1-6)alkoxy, di(C.sub.1-4 alkoxy)(C.sub.1-6)alkoxy, C.sub.2-6 alkenyloxy or C.sub.2-6 alkynyloxy and Z.sup.1 is hydrogen, fluorine, chlorine or C.sub.1-6 alkyl; or Y.sup.1 is methyl and Z.sup.1 is fluorine, chlorine or C.sub.1-6 alkyl; or, haloalkyl, C.sub.2-6 alkoxy, C.sub.1-6 alkylthio, C.sub.1-6 alkylsulphinyl, C.sub.1-6 haloalkoxy or C.sub.2-4 alkynyloxy and Z.sup.2 is hydrogen, fluorine, chlorine or C.sub.1-4 alkyl; or Y.sup.2 is methyl or methoxy and Z.sup.2 is fluorine, chlorine or C.sub.1-4 alkyl.
The compounds of the invention contain at least one carbon-carbon double bond, and are sometimes obtained in the form of mixtures of geometric isomers. However these mixtures can be separated into individual isomers, and this invention embraces such isomers, and mixtures thereof in all proportions.
The individual isomers which result from the unsymmetrically substituted double bond of the propenoate group are identified by the commonly used terms "E" and "Z". These terms are defined according to the Cahn-Ingold-Prelog system which is fully described in the literature (see, for example, J March, "Advanced Organic Chemistry", 3rd edition, Wiley-Interscience, page 109 et seq).
For the carbon-carbon double bond of the propenoate group, usually one isomer is more active fungicidally than the other, the more active isomer usually being the one wherein the group --CO.sub.2 CH.sub.3 and --OCH.sub.3 are on opposite sides of the olefinic bond of the propenoate group (the (E)-isomer). These (E)-isomers form a preferred embodiment of this invention.
Halogen includes fluorine, chlorine, bromine, and iodine.
REFERENCES:
patent: 5055471 (1991-10-01), de Fraine et al.
patent: 5104872 (1992-04-01), Tsubata et al.
Clough John M.
de Fraine Paul J.
Matthews Ian R.
Pilkington Brian L.
Worthington Paul A.
Thomson Marian T.
Tsang Cecilia
Zeneca Limited
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