Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1995-07-24
1998-01-13
Ford, John M.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514269, 514274, 544299, 544301, 544302, 544303, 544306, 544311, 544312, 544313, 544314, 544319, 544326, 544327, 544328, 544329, 544334, 544335, 544242, C07D23946, C07D23952, A01N 4354
Patent
active
057079951
DESCRIPTION:
BRIEF SUMMARY
This is a section 371 application of PCT/EP93/01880, filed Jul. 15, 1993.
The present invention relates to substituted pyrimidine compounds, their preparation and use as pesticides.
Dutch Patent Specification No. 6814057 discloses a wide range of substituted pyrimidines and their use as fungicides.
J. Indian Chem. Soc., 52(8), 1975, 774-775, and 53(9), 1976, 913-914 discloses a number of 2-amino-4,6-bis aryloxy and arylimino pyrimidines and suggests that they may have useful biological properties.
It has now been found that a group of substituted pyrimidines generically described in NL-6814057 but not specifically disclosed therein have acaricidal activity which is significantly greater than that of 2-amino-substituted analogues.
The present invention provides a compound of the general formula ##STR2## in which X.sup.1 and X.sup.2 are the same and each represents an oxygen atom; a group S(O).sub.n in which n is 0, 1 or 2; or a group CO, CH.sub.2 or NR in which R represents a hydrogen atom or an alkyl group; hydrogen atom or a halogen atom; hydrogen atom, a halogen atom or a cyano, nitro, alkyl, haloalkyl, alkoxy, alkylthio, amino, mono- or di-alkylamino, alkoxyalkyl, haloalkoxyalkyl or alkoxycarbonyl group; hydrogen atom, a chlorine atom, or an alkyl, haloalkyl, haloalkenyl, haloalkynyl, haloalkoxy, haloalkoxycarbonyl, haloalkylthio, haloalkoxyalkyl, haloalkylsulphinyl, haloalkylsulphonyl, nitro or cyano group; hydrogen atom, a halogen atom or an alkyl or alkoxy group; haloalkyl, alkoxy, alkylthio, alkylsulphinyl or phenyl group; and group; least one of R.sup.3 and R.sup.8 is other than hydrogen.
To maintain activity the phenyl rings of formula I must be either unsubstituted or at least one must be 3-substituted.
An alkyl group, unless otherwise specified, is suitably a straight chain or branched chain group containing up to 12 carbon atoms, for example up to 8 carbon atoms. Preferably an alkyl group contains up to 6 carbon atoms. Especially preferred alkyl groups are methyl, ethyl and butyl. Any alkyl moiety which forms part of another group, for example the alkyl of a haloalkyl group or each alkyl of an alkoxyalkyl group, suitably has up to 6 carbon atoms, preferably up to 4 carbon atoms. Preferred alkyl moieties are methyl and ethyl.
Halogen is fluorine, chlorine, bromine or iodine. Haloalkyl and haloalkoxy are especially trifluoromethyl, pentafluoroethyl, and trifluoromethoxy.
Preferably each of X.sup.1 and X.sup.2 represents an oxygen atom, a sulphur atom or an NH group; especially each of X.sup.1 and X.sup.2 represents an oxygen atom.
R.sup.1 and R.sup.10 are preferably the same and each represents a hydrogen or fluorine atom, especially a hydrogen atom.
R.sup.2 and R.sup.9 are preferably the same or different and each represents a hydrogen atom, a halogen atom, especially fluorine, chlorine or bromine, a nitro, alkyl or cyano group.
R.sup.3 and R.sup.8 are preferably the same or different, each representing a hydrogen, fluorine or chlorine atom, or a nitro, C.sub.1-4 alkyl, haloC.sub.1-4 alkyl, halo-C.sub.1-4 alkoxy, haloC.sub.2-4 alkenyl or (C.sub.1-4 alkoxy)carbonyl group. In especially preferred compounds each of R.sup.3 and R.sup.8 represents a hydrogen or chlorine atom or a trifluoromethyl, trifluoromethoxy, pentafluoroethyl or difluoroethenyl group or one of R.sup.3 and R.sup.8 represents a trifluoromethyl group and the other represents a hydrogen, chlorine or fluorine atom or a methyl, butyl, nitro, cyano or methoxycarbonyl group.
R.sup.4 and R.sup.7 are preferably the same or different and each represents a hydrogen or halogen atom or a C.sub.1-4 alkyl group.
The pyrimidine ring, apart from the substituents at the 4- and the 6-positions, may carry one other substituent. R.sup.5, in the 2-position, preferably represents a hydrogen or halogen atom or a halo C.sub.1-4 alkyl, C.sub.1-4 alkylthio, C.sub.1-4 alkylsulphinyl or phenyl group, especially a hydrogen, fluorine, chlorine or bromine atom or a methylthio or ethylthio group. R.sup.6, in the 5-position, preferably represents a hydrogen atom
REFERENCES:
patent: 5145856 (1992-09-01), Clough et al.
Chemical Abstracts 112:612g, vol. 112, 1990; Vainilavichius et al.
Shephard, Chemical Abstracts, vol. 72, entry 99507 (1970).
Netherlands Patent 6 81 4057 Derwent Abstract Aug. 31, 1993.
Davis Royston
Day Janet Anne
Munro David
Wilkin Jacqueline Anne
Wood William W.
American Cyanamid Company
Ford John M.
Hill Gregory M.
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