Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1995-04-11
1998-03-03
Berch, Mark L.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514309, 514310, 546141, 546142, 546145, 546334, 546335, 546300, 546283, 546174, 546153, 544298, 544309, 544311, 544312, 544313, 544314, 544315, 544316, 544317, 544318, 544319, 544320, 544321, 544322, 544323, 544324, 544325, 544326, 544327, 544328, 544329, 544330, 544331, 544332, 544333, 544334, 544335, 544219, 5482674, 5483751, 560 39, 549440, A01N 4742, C07D21756, C07D21762, C07D21722
Patent
active
057234736
DESCRIPTION:
BRIEF SUMMARY
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.
Fungicidal derivatives of propenoic acid including an oxime ether group, and having the general formula (I) are described in EP-A-0370629 and WO/GB92/00681 (published as WO92/18487), and these 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 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 present invention provides a compound of formula (I) wherein either: A is hydrogen, halogen, 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; and one of R.sup.1 and R.sup.2 is optionally substituted isoquinoline while the other is hydrogen, C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, halogen or cyano; or A is hydrogen, R.sup.2 is methyl and R.sup.1 is 4-tert-butylpyrid-2-yl, 4-tert-butylpyrimidin-2-yl, 5-methyl-6-iso-propoxypyrimidine-4-yl or 4-(C.sub.1-4 chlorofluoroalkyl)pyrid-2-yl (such as 4-ClF.sub.2 C-pyrid-2-yl or 4-Cl.sub.2 FC-pyrid-2-yl).
The compounds of the invention contain at least one carbon-nitrogen double bond and 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 and the oxime 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.
Substitutents which may be present in the optionally substituted isoquinoline moiety include one or more of the following: halogen, hydroxy, mercapto, C.sub.1-4 alkyl (especially methyl and ethyl), C.sub.2-4 alkenyl (especially allyl), C.sub.2-4 alkynyl (especially propargyl), C.sub.1-4 alkoxy (especially methoxy), C.sub.2-4 alkenyloxy (especially allyloxy), C.sub.2-4 alkynyloxy (especially propargyloxy), halo(C.sub.1-4)alkyl (especially trifluoromethyl), halo(C.sub.1-4)alkoxy (especially trifluoromethoxy), C.sub
REFERENCES:
patent: 5055471 (1991-10-01), De Fraine
patent: 5439910 (1995-08-01), De Fraine
Berch Mark L.
Kifle Bruck
Thomson Marian T.
Zeneca Limited
LandOfFree
Propenoic acid derivatives useful as fungicides does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Propenoic acid derivatives useful as fungicides, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Propenoic acid derivatives useful as fungicides will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2247877