Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Acyclic nitrogen double bonded to acyclic nitrogen – acyclic...
Patent
1995-07-24
1997-05-06
Higel, Floyd D.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Acyclic nitrogen double bonded to acyclic nitrogen, acyclic...
514149, 534556, 534566, 534558, 534572, C07C29108, A01N 5100
Patent
active
056271751
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 08 PCT/EP93/03370 filed Nov. 29, 1993.
This invention relates to certain azoxycyanobenzene derivatives, processes for their preparation, compositions containing such compounds and their use as fungicides.
Eur. J. Med. Chem.-Chimica Therapeutica, 12(1), (1977), pp. 59-62 discloses, inter alia, 2-methoxy-1-azoxycyanobenzene, 3-methoxy-1-azoxycyanobenzene and 4-methoxy-1-azoxycyanobenzene which are shown to have antibacterial and antifungal properties against bacteria and fungi of interest in the medical field. However, there is no indication that these compounds have any activity against phytopathogenic fungi of agronomic importance.
It has now been discovered that certain azoxycyanobenzene derivatives exhibit good activity against certain phytopathogenic fungi.
According to the present invention there is therefore provided a compound of general formula ##STR2## in which n is 0, 1, 2 or 3; each R independently represents a halogen atom, nitro, cyano, alkyl, haloalkyl, alkoxy or haloalkoxy group; and each of R.sup.1 and R.sup.2 independently represents an optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl or aralkyl group.
When the compounds of this invention contain an alkyl or alkenyl substitutent group, this may be linear or branched and may contain up to 12, preferably up to 6 and especially up to 4, carbon atoms. Cycloalkyl groups may contain 3 to 8, preferably 3 to 6, carbon atoms. An aralkyl group comprises an alkyl group, as defined above, substituted by an aryl group. The aryl group may be any aromatic hydrocarbon group, especially a phenyl or naphthyl group. A particularly preferred example of an aralkyl group is a benzyl group.
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, hydroxyl, alkyl, haloalkyl, alkoxy, haloalkoxy, phenoxy, amino, alkylamino, dialkylamino, formyl, alkoxycarbonyl, morpholinocarbonyl, carboxyl, alkanoyl, alkylthio, alkylsulphinyl, alkylsulphonyl, carbamoyl, alkylcarbamoyl and alkylamido groups. When any of the foregoing substituents represents or contains an alkyl substituent group, this may be linear or branched and may contain up to 12, preferably up to 6, and especially up to 4, carbon atoms. Typically, 0-3 substituents may be present, most commonly 0 or 1.
Preferably, each R independently represents a halogen atom, nitro, cyano, C.sub.1-6 alkyl, C.sub.1-6 haloalkyl, C.sub.1-6 alkoxy or C.sub.1-6 haloalkoxy group.
More preferably, each R independently represents a halogen (especially fluorine or chlorine) atom, C.sub.1-4 alkyl (especially methyl) or C.sub.1-4 haloalkyl (especially trifluoromethyl) group.
It is preferred that n is 0 or 1 and especially preferred that n is 0.
It is also preferred that each of R.sup.1 and R.sup.2 independently represents a C.sub.1-8 alkyl, C.sub.2-6 alkenyl, C.sub.2-6 alkynyl, C.sub.3-8 cycloalkyl or benzyl group, each group being optionally substituted by one or more substituents selected from halogen atoms, nitro, cyano, hydroxyl, C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, C.sub.1-4 alkoxy, C.sub.1-4 haloalkoxy, phenoxy, amino, C.sub.1-4 alkylamino, di-C.sub.1-4 alkylamino, C.sub.1-4 alkoxycarbonyl, morpholinocarbonyl, and C.sub.1-4 alkylcarbamoyl groups.
More preferably, each of R.sup.1 and R.sup.2 independently represents a C.sub.1-6 alkyl, C.sub.2-4 alkenyl, C.sub.2-4 alkynyl, C.sub.3-6 cycloalkyl or benzyl group, each group being optionally substituted by one or more substituents selected from halogen atoms, hydroxy, phenoxy, C.sub.1-4 alkyl, C.sub.1-4 alkoxycarbonyl, methylcarbamoyl and morpholinocarbonyl groups.
A particularly preferred sub-group of compounds of formula I is that in which n is 0 and each of R.su
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Mortarini et al., "Synthesis, Antibacterial and Antifungal Activity of Phenylazoxycyanide Derivatives", European Journal of Medicinal Chemistry, vol. 12, No. 1, 1977, pp. 59-62.
Costello, Jr. Charles F.
Higel Floyd D.
ShellInternationale Research Maatschappij B.V.
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