Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Phosphorus containing other than solely as part of an...
Patent
1991-10-18
1994-08-09
Dees, Jose G.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Phosphorus containing other than solely as part of an...
514112, 514114, 514116, 514120, 514121, 514125, 514126, 514129, 514131, C07F 954, A01N 5734
Patent
active
053366719
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to fungicidal compositions containing benzyl-tris(aryl)phosphonium compounds, some which are novel, and their use as fungicides.
It is known that many quaternary phosphonium salts are useful as bactericides (Jap. 18876/65), herbicides (U.S. Pat. No. 3,268,323; EP 73574) and nematicides (SA 67/3603). Also, U.S. Pat. No. 4,251,522 and EP 28493 disclose certain phenoxybenzylphosphonium salts and tris(aryl)alkyl phosphonium salts respectively which have fungicidal activity. However, many of these compounds, particularly alkyl-triphenyl phosphonium salts, show moderate to strong phytotoxicity when applied to plants or their activity against various fungi is too weak at non-phytotoxic concentrations. In particular, such phytopathogenic fungi as Botrytis cinerea or Plasmopara viticola are not well controlled by these compounds.
In addition, J. Org. Chem., 31(1), (1966), 334-336 discloses 4-methoxybenzyl-tris(4-methoxyphenyl)phosphonium bromide, U.S. Pat. No. 4,187,300 discloses 3,4-dichlorobenzyl-tris(3-methylphenyl)phosphonium chloride, benzyl-tris(2-methylphenyl)phosphonium chloride and 2,4-dichlorobenzyl-tris(4-methylphenyl)phosphonium phosphnium iodide and Z. anorg. allg. Chem., 551, (1987), 179-190 discloses benzyl-tris(4-t-butylphenyl)phosphonium hydrogen diiodide. However, none of these documents gives any indication that the compounds disclosed therein possess any fungicidal activity.
It has now been found that substituted benzyl-tris(aryl)phosphonium salts surprisingly exhibit excellent fungicidal activity, particularly against Botrytis cinerea and Plasmopara viticola, at low dosages and without phytotoxicity.
According to the present invention there is therefore provided a fungicidal composition which comprises a carrier and, as active ingredient, a compound of the general formula ##STR2## in which R.sup.1 represents an optionally substituted alkyl or alkoxy group; R.sup.2 represents a hydrogen atom or an optionally substituted alkyl group; R.sup.3, R.sup.4 and R.sup.5 independently represent a hydrogen or halogen atom or an optionally substituted alkyl or alkoxy group; and A.sup.- represents an anion.
When the compounds of this invention contain 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.
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, amino, alkylamino, dialkylamino, formyl, alkoxycarbonyl, carboxyl, alkanoyl, alkylthio, alkylsulphinyl, alkylsulphonyl, carbamoyl 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.
It is preferred that R.sup.1 represents a C.sub.1-6 alkyl or C.sub.1-6 alkoxy group. More preferably, R.sup.1 represents a C.sub.1-4 alkyl or C.sub.1-4 alkoxy group.
Preferably, R.sup.2 represents hydrogen atom or a C.sub.1-6 alkyl, especially a C.sub.1-4 alkyl, group.
It is preferred that R.sup.3, R.sup.4 and R.sup.5 independently represent a hydrogen or halogen, that is, a fluorine, chlorine, bromine or iodine, atom or a C.sub.1-4 alkyl or C.sub.1-4 alkoxy group.
Preferably, A.sup.- is an anion of an inorganic or organic acid. However, anions are preferred which are not phytotoxic. Examples of such anions are halides, especially chloride and iodide, thiocyanates, salicylates, saccharinares and sulphonic acid anions, especially optionally substituted alkyl or aralkyl sulphonates. Of these, chloride, iodide, thiocyanate and sulphonic acid anions are es
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CA 113(15):132186b, "Preparation of (diphenylpropyl)triazole derivatives as Aromokian Inhibitors and Plant Antiluregal Agents", (Boyl I Au), EP 354689A1, Feb. 14, 1990. Abstract only.
Johnson, A. W. et al., Chemistry Department University of North Dakota, "Chemistry of Ylids. XII. Effect of Phosphorus Substituents on the Stereochemistry of the Wittig Reaction", vol. 31, Jan. 1966, pp. 334-336.
Albert Guido
Becher Heinz-Manfred
Curtze Jurgen
Dees Jos,e G.
MacMillan Keith
Shell Research Limited
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