Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1996-08-07
1998-03-03
Ford, John M.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
544312, 544314, C07D23946, A01N 4354
Patent
active
057234710
DESCRIPTION:
BRIEF SUMMARY
This application is a 35 U.S.C..sctn.371 national stage filing of PCT/GB95/00999 filed 27 Feb., 1996.
The present invention relates to novel pyrimidine derivatives, to processes for preparing them, to compositions containing them and to methods of using them to combat fungi, especially fungal infections of plants. are described in EP-A-0242081 together with their use as fungicides. Specifically mentioned are the compounds, methyl now been found that the corresponding compounds containing a 4-(2,2,2-trifluoroethoxy) or 4-(1,1,1-trifluoroprop-2-oxy) substituent show unexpected advantages as plant fungicides in respect of vapour activity, foliar eradicant activity, spectrum of activity and/or systemicity.
Thus according to the present invention there is provided a compound of the general formula (I) (see later page of chemical formulae) or a stereoisomer thereof, wherein R is H or CH.sub.3, A is CH or N, and D is OCH.sub.3 or NHCH.sub.3.
Because the carbon--carbon or carbon-nitrogen double bond of the group DOC.C.dbd.A.OCH.sub.3 is unsymmetrically substituted, the compounds of the invention may be obtained in the form of mixtures of the (E)- and (Z)-geometric isomers. However, these mixtures can be separated into individual isomers by well known techniques, and this invention embraces such isomers and mixtures thereof in all proportions. The (E)-isomers are the more fugicidally active and therefore form a preferred embodiment of the invention.
In particular, the group W is CH.sub.3 O.N.dbd.C.CO.sub.2 CH.sub.3, CH.sub.3 O.N.dbd.C.CONHCH.sub.3 and more particularly CH.sub.3 O.CH.dbd.C.CO.sub.2 CH.sub.3.
In one aspect the invention provides the (E)-isomer of the compound of formula (I.1). In another aspect the invention provides the (E)-isomer of the compound of formula (I.4). In other aspects the invention provides the (E)-isomers of the compounds of formulae (I.2), (I.3), (I.5) and (I.6). when W is the group DOC.C.dbd.A.OCH.sub.3 ! can be prepared by the steps illustrated in Scheme I. Throughout Scheme I, R.sup.1 is an alkyl or aryl group, R.sup.2 is CF.sub.3 CH.sub.2 or CF.sub.3 CH(CH.sub.3), X is a halogen atom (eg Cl, Br, I), M is an alkali metal (eg sodium or potassium), T is hydrogen or an alkali metal (eg sodium or potassium), Ba is a base (eg sodium hydride or potassium carbonate), Ox is an oxidising agent (eg potassium permanganate or metachloroperbenzoic acid) and W is the group DOC.C.dbd.A.OCH.sub.3 defined above or a group that can be transformed into DOC.C.dbd.A.OCH.sub.3 using methods such as those already described in the literature.
The compounds of the invention can be prepared by reaction of the phenol of formula (II) with a pyrimidinyl sulphone of general formula (III), in the presence of a suitable base Ba. Alternatively, they can be prepared by reaction of a phenolate salt of formula (II) with the sulphone (III). Phenols of the formula (II), where W is DOC.C.dbd.A.OCH.sub.3, can be prepared by methods described in, for example, EP-A-0242081, EP-A-0398692 and GB-A-2249092. The compounds of formula (III) can be prepared from the thiopyrimidine of general formula (IV) by oxidation with a suitable oxidising agent Ox in a suitable solvent such as aqueous acetic acid. The thiopyrimidine of formula (IV) can be prepared from the thiopyrimidine (V) by reaction with an alkoxide of formula R.sup.2 OM in a suitable solvent such as N,N-dimethylformamide (DMF) or tetrahydrofuran (THF). The compound (V) where X is chlorine is available commercially.
Alternatively the compound of formula (I) can be prepared from the pyrimidine of general formula (VI), by reaction with an alkoxide of formula R.sup.2 OM, in a suitable solvent such as DMF. Compounds of general formula (VI) can be prepared by treating the phenol of formula (II) with a sulphone of general formula (VII) using a base Ba in a suitable solvent such as DMF. The sulphone of formula (VII) can be prepared from the pyrimidine of formula (V) by oxidation with a suitable oxidising agent Ox in a suitable solvent such as aqueous acetic acid or dichlorometha
Ford John M.
Snyder Joseph R.
Zeneca Limited
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