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United States Patent Office Patented Apr 3,574,851 United States Patent Office Patented Apr. 3, 1971 2 trihexyl (4-nitrosotolyl)ammonium bromide, 3,574,851 dimethylhexyl (4-nitrosotolyl)ammonium chloride, FUNGCDAL METHOD EMPLOYING NEW dihexylmethyl (4-nitrosotolyl)ammonium iodide, QUATERNARY AMMONUM HALDES Asher A. Hyatt, Lexington, Mass., assignor to Monsanio diethylpentyl (4-nitrosotolyl)ammonium fluoride, Research Corporation, St. Louis, Mo. butyldipropyl (4-nitrosotolyl)ammonium bromide, No Drawing. Original application Dec. 3, 1965, Ser. No. butylhexylmethyl (4-nitrosotolyl)ammonium chloride, 531,320, now Patent No. 3,390,178, dated June 25, trimethyl(4-nitrosoxylyl)ammonium fluoride, 1968. Divided and this application Dec. 20, 1967, Ser. triethyl (4-nitrosoxylyl)ammonium chloride, No. 721,893 tripropyl (4-nitrosoxylyl)ammonium bromide, nt. C. AOn 9/20 O tributyl (4-nitrosoxylyl)ammonium iodide, U.S. C. 424-329 2 Claims tripentyl (4-nitrosoxylyl)ammonium fluoride, trihexyl (4-nitrosoxylyl)ammonium chloride, dimethylhexyl (4-nitrosoxylyl)ammonium fluoride, ABSTRACT OF THE DISCLOSURE dihexylmethyl (4-nitrosoxylyl)ammonium chloride, A method of controlling soil fungi employing certain 15 diethylphentyl (4-nitrosoxylyl)ammonium bromide, new nitroso substituted aryl derivatives of trialkyl ammo butyldipropyl (4-nitrosoxylyl)ammonium iodide, nium halides. butylhexylmethyl (4-nitrosoxylyl)ammonium fluoride, trimethyl(4-nitrosonaphthyl)ammonium iodide, triethyl (5-nitrosonaphthyl)ammonium fluoride, This is a division of application Ser. No. 531,320 filed tripropyl (6-nitrosonaphthyl)ammonium chloride, Dec. 3, 1965, now Patent No. 3,390,178. tributyl (4-nitrosonapththyl)ammonium bromide, This invention relates to the reaction of nitroso sub tripentyl (5-nitrosonaphthyl)ammonium iodide, stituted aromatic hydrocarbon derivatives of dialkyl trihexyl (6-nitrosonaphthyl)ammonium fluoride, amines with alkyl halides and to the products thereof. dimethylhexyl (4 - nitrosonaphthyl)ammonium chloride, It is an object of this invention to provide new nitroso 25 dihexylmethyl (4-nitroSonaphthyl)ammonium bromide, substituted aryl derivatives of trialkyl ammonium halides. diethylpentyl (6-nitrosonaphthyl)ammonium iodide, It is another object of this invention to provide com butyldipropyl (4-nitrosonaphthyl)ammonium fluoride, pounds useful as biological toxicants such as fungicides, butylhexylmethyl (5-nitrosonaphthyl)ammonium plant growth regulators, defoliants, insecticides and bromide, bactericides. 30 trimethyl(3'-nitrosobiphenlyl)ammonium chloride, According to the invention, there are prepared new triethyl (2'-nitrosobiphenylyl)ammonium fluoride, and useful compounds having the formula: tripropyl (3'-nitrosobiphenylyl)ammonium bromide, tributyl (4'-nitrosobiphenylyl)ammonium iodide, R. 69 tripentyl(4'-nitrosobiphenylyl)ammonium chloride, R-N-R, Xe 35 trihexyl (3'-nitrosobiphenylyl)ammonium fluoride, RNO dimethylhexyl (2'-nitrosobiphenylyl)ammonium. wherein R1 represents bivalent aromatic hydrocarbon bromide, radicals of from 6 to 12 carbon atoms, each of R2, R3, dihexylmethyl (4 - nitrosobiphenylyl)ammonium iodide, and R4 represents alkyl radicals free of aliphatic un and so forth. saturation of from 1 to 6 carbon atoms and X represents 40 Useful nitroso-substituted aromatic hydrocarbon deriv a halogen element of atomic weight below 130. atives of dialkylamines are, for example: Preparation of the presently provided novel com N,N-dimethyl-p-nitrosoaniline, pounds is effected by contacting the alkyl halide with the N,N-dihexyl-p-nitrosoaniline, nitroso substituted aromatic hydrocarbon derivative, N-hexyl-N-methyl-p-nitrosoaniline, according to the following equation: N,N-diethyl-m-nitrosoaniline, N,N-dipropyl-o-nitrosoaniline, N,N-dibutyl-m-nitrosoaniline, is N,N-dipentyl-m-nitrosoaniline, R-N-R, -- RX --> t X N-ethyl-N-pentyl-p-nitrosoaniline, RNO RNO 50 N-butyl-N-propyl-p-nitrosoaniline, wherein R1, R2, R3, R4 and X are as defined above. N-methyl-N-propyl-o-nitrosoaniline, There are shown below a number of the specific new N,N-dimethylp-nitrosotoluidine, compounds of the invention. It is not intended that this N,N-dihexyl-m-nitrosotoluidine, be a complete listing of all compounds of the invention, N-hexyl-N-methyl-o-nitrosotoluidine, but that it merely be illustrative thereof: 55 N.N-diethyl-m-nitrosotoluidine, trimethyl (p-nitrosophenyl)ammonium iodide, N,N-dipropyl-p-nitrosotoluidine, triethyl(o-nitrosophenyl)ammonium bromide, N,N-dibutyl-o-nitrosotoluidine, tripropyl (m-nitrosophenyl)ammonium chloride, N,N-dipentyl-m-nitrosotoluidine, tributyl (p-nitrosophenyl)ammonium fluoride, N-ethyl-N-pentyl-p-nitrosotoluidine, tripentyl (o-nitrosophenyl)ammonium iodide, 60 N-butyl-N-propyl-o-nitrosotoluidine, trihexyl (m-nitrosophenyl)ammonium bromide, N-methyl-N-propyl-m-nitrosotoluidine, dimethylhexyl (p-nitrosophenyl)ammonium chloride, N,N-dimethyl-p-nitrosoxylidine, dihexylmethyl (o-nitrosophenyl)ammonium fluoride, N,N-dihexyl-p-nitrosoxylidine, diethylpentyl (m-nitrosophenyl)ammonium iodide, N-hexyl-N-methyl-p-nitrosoxylidine, butyldipropyl (p-nitrosophenyl)ammonium bormide, N,N-diethyl-m-nitrosoxylidine, butylhexylmethyl (o - nitrosophenyl)ammonium chloride, N,N-dipropyl-o-nitrosoxylidine, trimethyl(4-nitrosotolyl)ammonium fluoride, N,N-dibutyl-p-nitrosoxylidine, triethyl (4-nitrosotolyl)ammonium iodide, N,N-dipentyl-m-nitrosoxylidine, tripropyl (4-nitrosotolyl)ammonium bromide, N-ethyl-N-pentyl-p-nitrosoxylidine, tributyl (4-nitrosotolyl)ammonium chloride, 70 N-butyl-N-propyl-p-nitroxylidine, tripentyl (4-nitrosotolyl)ammonium fluoride, N-methyl-N-propyl-m-nitroxylidine, 3,574,851 3 4. 4-nitroso-N,N-dimethylnaphthylamine, (ml.) of 2-propanol is gradually added 23.7 g. (about 4-nitroso-N,N-dihexylnaphthylamine, 0.17 mole) of iodomethane. The mixture is refluxed for 4-nitroso-N,N-diethylnaphthylamine, two and one-half hours to insure complete reaction and 4-nitroso-N,N-dipropylnaphthylamine, then filtered. The crude residue is washed several times 4-nitroso-N,N-dibutylnaphthylamine, with each of 2-propanol, acetone, and ether, then dried. 4-nitroso-N,N-dipentylnaphthylamine, 5 The resulting product is trimethyl (p-nitrosophenyl)- 4-nitroso-N-ethyl-N-pentylnaphthylamine, ammonium iodide, a uniformly green crystalline solid 4-nitroso-N-butyl-N-propylnaphthylamine, weighing 27 g. (about 55% theoretical yield), soluble in 4-nitroso-N-methyl-N-propylnaphthylamine, dimethylsulfoxide and melting at 154-155° C. 4'-nitroso-N,N-dimethylbiphenylylamine, Elemental analysis of this product confirms the assigned 4'-nitroso-N,N-dihexylbiphenylylamine, O empirical formula C9H13INO: '-nitroso-N-hexyl-N-methylbiphenylamine, Calculated (percent): C, 37.0; H, 4.5; I, 43.5. Found 4'-nitroso-N,N-diethylbiphenylamine, (percent): C, 36.8; H, 4.0; I, 43.5. 4'-nitroso-N,N-dipropylbiphenylylamine, 4'-nitroso-N,N-dibutylbiphenylylamine, EXAMPLE 2. 4'-nitroso-N,N-dipentyl-biphenylylamine, 15 This example describes the utilization of a compuond -nitroso-N-ethyl-N-pentylbiphenylamine, of this invention as a bactericide. 4'-nitroso-N,N-diphenyl-biphenylylamine, To test bactericidal activity, inoculations of S. aureous, 4'-nitroso-N-methyl-N-propylbiphenylylamine, S. typhosa, and A. niger, are made on agar substrates sup porting the growth of these microorganisms, to which has and so forth. been added varying amounts of trimethyl (p-nitroso Useful alkyl halides are, for example: iodomethale, phenyl)ammonium iodide. The inoculated plates are fluoroethane, 1-chloropropane, 1-bromobutane, 1-iodo maintained under conditions supporting growth of these pentane, 1-fluorohexane, 2-chloropropane, 1-bromoiso microorganisms. At concentrations of 1 part per 1,000 and butane, 2-iodo-2-methyl-propane, 2,2-dimethyl-1-fluoro 1 part per 10,000 in the agar, the ammonium compound propane, 1-bromoisopentane, and so forth. causes substantially complete suppression of growth and In carrying out the process of this invention, the nitroso compound is simply contacted with the alkyl halide until reproduction of each of the microorganism species. the reaction is complete. It is an advantage in moderat EXAMPLE 3 ing the reaction to add one of the reactants slowly and gradually to the other, though the reactants may optionally 30 To test defoliant activity, Black Valentine bean plants, be added all at once, preferably together with a solvent 4 to a pot, are grown to the stage of having 1 mature or diluent, Solvents or diluents which may be used to trifoliate and 1 partially opened trifoliate, and then sprayed moderate the reaction and to facilitate stirring, and so With trimethyl (p-nitrosophenyl)ammonium iodideasan forth, are alcohols, such as methanol, ethanol and pro aqueous emulsion, at rates of 0.1 and 1.0 pound per acre panol, for example. 35 (lbs./A.), using a dilution of 30 gallons per acre, after The ratio of reactants may very, molar ratios of the which the plants are maintained in a greenhouse within nitroso compound to the alkyl halide compound of at temperature limits of 70°-90° F. The plants are de least 1:10 to about 10:1 may be used, but since the re foliated in the 50% range at both rates. Defoliation in action is equimolar, advantageously a 1:1 ratio of re the 51.75% range is observed when the same compound actants is employed. Excess reactant may be removed 40 is applied to soybean plants at the rate of 10 lbs./A. at the end of the reaction by, for example, extraction or EXAMPLE 4 distillation. o This example illustrates the use of a compound of this Useful temperatures for conducting the preparation are, invention
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