Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1995-08-28
1998-12-29
Lambkin, Deborah C.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
544263, A61K 31505, C07D48700
Patent
active
058542523
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP94/00635 filed Mar. 3, 1994.
This invention relates to certain dihalotriazolopyrimidine derivatives, some of which are novel, processes for their preparation, compositions containing such compounds and their use as fungicides.
Chemical Abstracts (1964), 61:2941 g discloses the preparation of oxychloride for 4 hours at 100.degree. C. However, there is no indication that either of these compounds exhibits biological activity.
Applicant's co-pending European application no. 92204097.7 (EP-A-0550113) discloses compounds of the general formula. ##STR2## in which R.sup.3 represents an optionally substituted aryl group and X and Y both represent a chlorine atom or both represent a bromine atom, as intermediates in the preparation of certain fungicidally active triazolopyrimidine derivatives of the general formula ##STR3## in which R.sup.1 represents an optionally substituted alkyl, alkenyl, alkynyl, alkadienyl, cycloalkyl, bicycloalkyl or heterocyclyl group; R.sup.2 represents a hydrogen atom or an alkyl group; or R.sup.1 and R.sup.2 together with the interjacent nitrogen atom represent an optionally substituted heterocyclic ring; R.sup.3 is as defined above, and R.sup.4 represents a hydrogen or halogen atom or a group --NR.sup.5 R.sup.6 where R.sup.5 represents a hydrogen atom or an amino, alkyl, cycloalkyl or bicycloalkyl group and R.sup.6 represents a hydrogen atom or an alkyl group. However, there is no indication in this document that the compounds of formula A themselves possess any fungicidal activity.
It has now been discovered that certain compounds of formula A and certain further novel dihalotriazolopyrimidine derivatives exhibit fungicidal activity in their own right.
According to the invention there is therefore provided a fungicidal composition which comprises a carrier and, as active ingredient, a compound of the general formula ##STR4## in which R represents an optionally substituted branched or straight-chain alkyl or alkoxy group, or an optionally substituted cycloalkyl, aryl, aryloxy or heterocyclyl group, and Hal represents a fluorine, chlorine, bromine or iodine atom.
When the compounds in the compositions of this invention contain a cycloalkyl group, this may contain from 3 to 8, preferably 3 to 6, carbon atoms. An aryl group may be any aromatic hydrocarbon group, especially a phenyl or naphthyl group. A heterocyclyl group may be any saturated or unsaturated ring system containing at least one heteroatom, 3- to 6-membered rings being preferred and 5- and 6-membered rings being especially preferred. Nitrogen-, oxygen- or sulphur-containing rings, such as pyridinyl, pyrimidinyl, pyrrolidinyl, furyl, pyranyl, morpholinyl and thienyl, are particularly preferred.
When any of the foregoing substituents are designated as being optionally substituted, the substituent groups which are optionally present may be any one or more of those customarily employed in the development of pesticidal compounds and/or the modification of such compounds to influence their structure/activity, persistence, penetration or other property. Specific examples of such substituents include, for example, halogen atoms, nitro, cyano, thiocyanato, cyanato, hydroxyl, alkyl, haloalkyl, alkoxy, haloalkoxy, amino, alkylamino, dialkylamino, formyl, alkoxycarbonyl, carboxyl, alkanoyl, alkylthio, alkylsulphinyl, alkylsulphonyl, halosulphonyl, carbamoyl, alkylamido, phenyl, phenoxy, benzyl and benzyloxy, heterocyclyl, especially furyl, and cycloalkyl, especially cyclopropyl, groups. Typically, 0-3 substituents may be present.
When any of the foregoing substituents represents or contains an alkyl group, this may be linear or branched and may contain up to 12, preferably up to 6, and especially up to 4, carbon atoms. When any of the foregoing substituents represents or contains an aryl or cycloalkyl moiety, the aryl or cycloalkyl moiety may itself be substituted by one or more halogen atoms, nitro, cyano, alkyl, haloalkyl, alkoxy or haloalkoxy groups. In the case of cycloalkyl and heterocyclyl groups,
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Becher Heinz-Manfred
Pees Klaus-Jurgen
Costello, Jr. Charles F.
Lambkin Deborah C.
Shell Internationale Research Maatschappij B.V.
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