US3525603A

US3525603A - Method of increasing the sugar content of sugar cane

Info

Publication number: US3525603A
Application number: US769407A
Authority: US
Inventors: Philip C Hamm
Original assignee: Monsanto Co
Current assignee: Monsanto Co
Priority date: 1968-10-21
Filing date: 1968-10-21
Publication date: 1970-08-25
Anticipated expiration: 1987-08-25

Description

United States Patent 3,525,603 METHOD OF INCREASING THE SUGAR CONTENT OF SUGAR CANE Philip C. Hamm, Glendale, Mo., assiguor to Monsanto Company, St. Louis, Mo., a corporation of Delaware No Drawing. Continuation-impart of application Ser. No. 582,223, Sept. 27, 1966. This application Oct. 21, 1968, Ser. No. 769,407

Int. Cl. A01n 9/14 US. Cl. 71-103 12 Claims ABSTRACT OF THE DISCLOSURE Increasing the sugar content of sugar cane by contacting the sugar cane with substituted benzenesulfonyl ureas and its salts.

This application is a continuation-in-part of application Ser. No. 582,223, filed Sept. 27, 1966, now abandoned.

In accordance with this invention, the sugar content of sugar cane is increased by a method which comprises applying to maturing sugar cane one or more compounds selected from the group consisting of (I) Compounds having the formula wherein X is selected from the group consisting of chloro, bromo, iodo and fiuoro; Y is selected from the group consisting of alkyl, alkoxy, alkenyl and alkynyl each of which has a maximum of 12 carbon atoms; Z is selected from the group consisting of N0 NH NO, CN and i NHCR wherein R is selected from the group consisting of hydrogen and alkyl having a maximum of 12 carbon atoms; a is an integer from 0 to 5, inclusive; b is an integer from 0 to 3, inclusive; c is an integer from 0 to 1, inclusive; M is a salt-formnig cation selected from the group consisting of alkali metals, alkaline earth metals, ammonium and aliphatic-substituted ammoniums; and n is the valence of M, said compound being applied in an amount sufiicient to increase the sugar content of the sugar cane but in an amount insufficient to exert a herbicidal action.

In the above formula Y can be alkyl such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, amyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl and the various homologues and isomers of alkyl having not more tan 12 carbon atoms, alkenyl such as vinyl allyl, n-butenyl-l, n-butenyl-2, n-pentenyl-Z, nhexenyl-Z, 2,3-dimethylbutenyl-2, n-heptenyl, n-decenyl, n-dodecenyl and the various homologues and isomers of alkenyl having not more than 12 carbon atoms, alkynyl such as ethynyl, propargyl, 3-hexynyl and the various homologues and isomers of alkynyl having not more than 12 carbon atoms, and alkoxy such as methoxy, ethoxy, butoxy, hexoxy, heptoxy and the various homologues and isomers of alkoxy having not more than 12 carbon atoms. R as alkyl can be any of the alkyl listed above for Y.

The aliphatic-substituted ammonium salts are those prepared from low molecular aliphatic amines, i.e., having a molecular weight below about 300, and more particularly the alkyl amines, alkylene amines and alkanol amines containing not more than 2 amine groups such as methylamine, ethylamine, n-propylamine, isopropylamine, n-butylamine, isobutylamine, sec-butylamine, namylamine, iso-amylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, undecylamine, dodecylamine, tridecylamine, tetradecylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, methylethylamine, methylisopropylamine, methylhexylamine, methylnonylamine, methylpentadecylamine, methyloctadecylamine, ethylbutylamine, ethylheptylamine, ethyloctylamine, hexylheptylamine, hexyloctylamine, dimethylamine, diethylamine, di-n-propylamine, diisopropylamine, di-n-butylamine, diisobutylamine, disec-butylamine, di-n-amylamine, diisoamylamine, dihexylamine, diheptylamine, dioctylamine, trimethylamine, triethylamine, tri-n-propylamine, triisopropylamine, tri-nbutylamine, triisobutylamine, tri-sec-butylamine, tri-namylamine, ethanolamine, n-propanolamine, isopropanolamine, diethanolamine, tri-N-ethylethanolamine, N-ethylpropanolamine, N-butylethanolamine, allylamine, nbutenyl-2-amine, n-pentenyl-Z-amine, 2,3-dimethylbutenyl-Z-amine, dibutenyl-Z-amine, n-hexenyl-Z-amine, and propylenediamine.

The preferred compounds are selected from the group consisting of wherein X is selected from the group consisting of chloro, bromo, iodo and fluoro; a is an integer 0 to 2, inclusive; Y is selected from the group consisting of alkyl and alkoxy having a maximum of four carbon atoms; b is an integer 0 to l, inclusive; Z is selected from the group consisting of N0 NH and if NHCR wherein R is selected from the group consisting of hydrogen and alkyl having a maximum of 5 carbon atoms; 0 is an integer O to 1, inclusive, M is selected from the group consisting of alkali metal, alkaline earth metal, ammonium and substituted ammonium of the formula Hl 3R R R wherein R R and R are each independently selected from the group consisting of hydrogen, alkyl, alkenyl and hydroxyalkyl each having a maximum of 4 carbon atoms.

It is known that the anionic portion of the salts is a resonance hybrid having the terminology of isourea and urea depending upon the charge location. For convenience the terminology of is-ourea" will be used in this specification and appended claims to designate the salts of the resonance hybrid, and the term urea will be used to designate the free base.

The ureas and isourea salts are applied to the maturing sugar cane prior to the time the sugar cane has reached maximum sugar content or the complete ripening thereof. The application of the ureas and isourea salts to sugar cane is carried out at more than about one week prior 3 to harvest but not more than about 4 months prior to harvest. Application not more than about 2 months prior to harvest is particularly advantageous.

As mentioned hereinbefore, the ureas and isourea salts are applied in an amount suflicient to increase the sugar content of the sugar cane, but in an amount insufficient to exert a herbicidal action. Such amounts are determined by and dependent upon the particular urea or isourea salt selected, the method of application, the state and condition of growth of the sugar cane, and the climatic conditions. An increase in sugar content of sugar cane without herbicidal action is obtained in most instances by the application of the ureas or isourea salts in an amount from about 0.1 to about 10 pounds per acre. The preferred application rate is from about 3 pounds to about 7 pounds of isourea salt per acre.

The isourea salts useful in the methods of this invention and processes for making them are well known in the art. They can be prepared by reacting an arylsulfonamide with a suitable cyanate. For example, potassium 1-(p-nitrobenzenesulfonyl) isourea can be prepared by heating substantially equimolar amounts of p-nitrobenzenesulfamide and potassium cyanate in the presence of an aqueous medium under reflux for about 8 hours, cooling the reaction mixture and recovering the product by filtration. More detailed procedures for the preparation of various p-su'bstituted benzenesulfonylisourea salts are set forth in Martin et al. US. Pat. 2,411,661 (Nov. 26, 1946) and Haack US. Pat. 2,385,571 (Sept. 25, 1945), and the disclosures thereof are incorporated herein by reference.

The following examples illustrate the invention. Parts and percent are by weight unless otherwise indicated.

EXAMPLE 1 Six month old sugar cane (Finder) plants grown under greenhouse conditions at a temperature from about 70 F. to about 90 F. and 65% relative humidity are sprayed with acetone-water solutions containing a small amount of emulsifier and various amounts of calcium l-(p-nitrobenzenesulfonyl)isourea at a rate equivalent to about 70 gallons of spray per acre. The sprays are applied at rates of one and ten pounds of isourea salt per acre using Randomized Block with six replications of each application rate including control (no active ingredient). Harvesting is carried out three weeks after spraying and the amount of sucrose is measured and recorded. Results and further details are given in Table I wherein results are expressed as a percent of the control.

TABLE I Total wt. of sucrose Application rate, lb./ acre: per stalk Control 100 EXAMPLE 2 TABLE II.PERCENT FRESH WEIGHT OF SUCROSE IN STALKS Harvest Application rate, lb./acre 4 weeks 8 weeks Control (0) 100 100 .2 134 163 4 EXAMPLE 3 Repeating Example 1, using p-aminobenzenesulfonylurea (A) or potassium 1-(pbromobenzenesulfonyl)- isourea (B) in place of the calcium derivative yielded the results, in percent of the control, listed in Table III.

TABLE III Total Weight of Sucrose Per Stalk Application rate, lb./acre (A) Control (0) 100 l 117 109 121 104 128 103 calcium 1-(p-chlorobenzenesulfonyl)isourea calcium 1- (p-methylbenzenesulfonyl) isourea sodium 1-(p-nitrobenzenesulfonyl) isourea sodium 1- (p-methoxybenzene sulfonyl)isourea magnesium 1-(p-chlorobenzenesulfonyl)isourea magnesium lp-butenyl-2-benzenesulfonyl isourea calcium 1-(p-aminobenzenesulfonyl)isourea calcium 1-(p-cyanobenzenesulfonyl)isourea sodium 1-(p-chlorobenzenesulfonyl)isourea magnesium 1-(3,4-dichlorobenzenesulfonyl) isourea potassium 1-(p-nitrosobenzenesulfonyl)isourea sodium 1-(pchlorobenzenesulfonyl)isourea calcium 1-(3,4-dichlorobenzenesulfonyl)isourea calcium 1-(p-acetylaminobenzenesulfonyl)isourea magnesium 1-(p-nitrobenzenesulfonyl)isourea magnesium 1- 3 ,4,S-trichlorobenzenesulfonyl isourea barium 1-(p-a-minobnezenesulfonyl)isourea magnesium 1-(p-aminobenzenesulfonyl)isourea magnesium 1-(3-aminobenzenesulfonyl)isourea ammonium 1-(p-nitrobenzenesulfonyl)isourea ammonium l-(2,4-dimethylbenzlenesulfonyl)isourea ethylamine salt of p-nitrobenzenesulfonyl isourea diethylamine salt of p-nitrobenzenesulfonyl isourea propylamine salt of p-nitrobenzenesulfonyl isourea triethylamine salt of p-nitrobenzenesulfonyl isourea N-methylethylamine salt of p-nitrobenzenesulfonyl isourea ethanolamine salt of p-nitrobenzenesulfonyl isourea diethanolamine salt of p-nitrobenzenesulfonyl isourea ethanolamine salt of p-aminobenzenesulfonyl isourea allylamine salt of p-nitrobenzenesulfonyl isourea ethanolamine salt of p-acetylaminobenzenesulfonyl isourea diethylamine salt of n-butylcarbonylaminobenzenesul fonyl isourea p-aminobenzenesulfonyl urea p-nitrobenzenesulfonyl urea p-chlorobenzenesulfonyl urea 3 ,4-dichlorobenzenesulfonyl urea p-nitrosobenzenesulfonyl urea p-acetylbenzenesulfonyl urea p-cyanobenzenesulfonyl urea 3,4,S-trichlorobenzenesulfonyl urea p-methylbenzenesulfonyl urea p-methoxybenzenesulfonyl urea 2,4-dimethylbenzenesulfonyl urea p-n-buteny1-2-benzenesulfonyl urea For the sake of brevity, the term active ingredien is used hereinafter in this specification to describe the ureas and isourea salts useful in accordance with the methods of this invention.

In practicing the methods of this invention, the active ingredients can be used alone or in combination with an adjuvant in liquid or solid form. The compositions are prepared by admixing the active ingredient with an adjuvant including diluents, extenders, spreaders, adhesives, carriers and conditioning agents to provide compositions in the form of finely-divided particulate solids, solutions, dispersions or emulsions. Thus the active ingredient. can be used with an adjuvant such as a finelydivided particulate solid, at liquid of organic origin, water, a .wetting agent, dispersing agent, an emulsifying agent or any suitable combination of these.

Typical finely-divided solid carriers and extenders which can be used in the compositions of this invention include, for example, the tales, clays, pumice, silica, lime, calcium carbonate, diatomaceous earth, quartz, fullers earth, salt, sulfur, powdered cork, powdered wood, cotton seed hulls, wheat flour, soybean flour, walnut flour, chalk, tobacco dust, volcanic ash, charcoals and the like. Typical liquid diluents include for example, water, kerosene, Stoddard solvent, hexane, benzene, toluene, acetone, ethylene dichloride, xylene, alcohols, diesel oil, glycols and the like.

The compositions useful in this invention, particularly liquids and wettable particles, usually contain as a conditioning agent one or more surface-active agents in amounts sufficient to render a given composition readily dispersible in water or in oil. By the term surface-active agenf it is understood that wetting-agents, dispersing agents, suspending agents and emulsifying agents are included therein.

Preferred compositions containing the active ingredients have been developed so that the active ingredients can be used to the greatest advantage to increase the sugar content of sugar cane. The preferred compositions comprise certain wettable powders, aqueous suspensions, dust formulations, emulsi'fiable oils and solutions in solvents. In general these preferred compositions all contain one or more surface-active agents.

Surface-active agents which can be used in the compositions useful in this invention are set out, for example, in Searle US. Pat. 2,426,417, Todd US. Pat. 2,655,447, Jones US. Pat 2,412,510 and Lenher US. Pat. 2,139,276. A detailed list of such agents is also set forth by J. W. McCutcheon in Soap and Chemical Specialties, November 1947, page 8011 et seq., entitled Synthetic Detergents; Detergents and Emulsifiers-Up to Date (1960), by J. W. McCutcheon, Inc., and Bulletin E-607' of the Bureau of Entomology and Plant Quarantine of the U.S.D.A. In general, less than 50 parts by weight of the surface-active agents is present per 100 parts by weight of the composition.

Wettable powders are water-dispersible compositions containing one or more active ingredients, an inert solid extender and one or more wetting and dispersing agents, The inert solid extenders are usually of mineral origin such as the natural clays, diatomaceous earth and synthetic minerals derived from silica and the like. Examples of such extenders include kaolinites, attapulgite clay and synthetic magnesium silicate.

Preferred wetting agents are alkali metal alkylaryl sulfonates, sulfated fatty alcohols, amines or acid amides, long chain acid esters of sodium isethionate, esters of sodium sulfosuccinate, sulfated or sulfonated fatty acid esters, petroleum snlfonates, sulfonated vegetable oils, ditertiary acetylinic glycols, polyoxyethylene derivatives of alkylphenols (particularly isooctylphenol and nonylphenol) and polyoxyethylene derivatives of mono-higher fatty acid esters of hexitol anhydrides (e.g. sorbitan). Preferred dispersants are methyl cellulose, polyvinyl alcohol, sodium lignin sulfonates, polymeric alkyl naphthalene sulfonates, sodium naphthalene sulfonate, polymethylene bisnaphthalenesulfonate and sodium N-methyl- N-(long chain acid) taurates.

The wettable powder compositions usually contain from about to about 95 parts of active ingredient, from about 0.25 part to about 25.0 parts of wetting agent, from about 0.25 part to about 7 parts of dispersant and from about 4.5 to about 94.5 parts of inert solid extender, all parts being by weight of the total composition. Where required from about "0.1 to 2.0 parts by weight of the solid inert extender can be replaced by a corrosion inhibitor or antifoaming agent or both. If the particular active ingredient selected is water-soluble, the solution formed by admixture with water or other aqueous media can be employed in the methods of this invention without further formulation.

Emulsifiable oils are usually solutions of active ingredient in Water-immiscible solvents together with a surfactant. Suitable surfactants are anionic, cationic and nonionic such as alkylaryl polyethoxy alcohols, polyethylene sorbital or sorbitan fatty acid esters, polyethylene glycol fatty esters, fatty alkylol amide condensates, amine salts of fatty alcohol sulfates together with long chain alcohols and oil soluble petroleum sulfonates or mixtures thereof. The emulsifiable oil compositions generally contain from about 5 to parts active ingredient, about 1 to 50 parts surfactant and about 4 to 94 parts solvent, all parts being by weight based on the total weight of emulsifiable oil.

When operating in accordance with the present invention, effective amounts of the active ingredients are applied to sugar cane plants in any convenient fashion. The application of the compositions to the sugar cane can be carried out by conventional methods, e.g., power dusters, boom and hand sprayers and spray dusters. The compositions can also be applied from airplanes as a dust or a spray because of their effectiveness at low dosages.

Herbicidal compositions containing as an active ingredient therein many of the above ureas and isourea salts are disclosed and claimed in copending application Ser. Nos. 210,220 and 210,242, both filed July 16, 1962, and copending application Ser. No. 406,884, filed Oct. 25, 1964, which in turn is a division of application Ser. No. 210,217, filed July 16, 1962, and now abandoned.

The terms amine and aliphatic substituted ammonium as used herein mean only those ammonium and amine compounds wherein each valence of the nitrogen atom is attached to a different hydrogen or carbon atom.

Although the invention is described with respect to speci'fic modifications, the details thereof are not to be construed as limitations except to the extent indicated in the following claims.

While the illustrative embodiments of the invention have been described hereinbefore with particularity, it will be understood that various other modifications will be apparent to and can readily be made by those skilled in the art without departing from the scope and spirit of the invention.

What is claimed is:

1. Method of increasing the sugar content of sugar cane which comprises applying to sugar cane a compound selected from the group consisting of compounds having the formula (a) o o W LNHtN...

and

wherein R is selected from the group consisting of chloro, bromo, fluoro, iodo, nitro and NH M is a salt-forming cation selected from the group consisting of alkali metals, alkaline earth metals, ammonium and substituted ammonium of the formula wherein R R and R are each independently selected from the group consisting of hydrogen, alkyl, alkenyl and hydroxyalkyl each having a maximum of 4 carbon atoms; and n is the valence of M, said compound being wherein R is selected from the group consisting of chloro, bromo, fiuoro, iodo, nitro and NH 6. Method of claim 5 wherein the compound is paminobenzenesulfonyl urea.

7. Method in accordance with claim 1, in which the compounds have the formula ll 0 D wherein R is selected from the group consisting of chloro, bromo, fluoro, iodo, nitro and NH M is a salt-forming cation selected from the group consisting of alkali metals, alkaline earth metals, ammonium and substituted ammonium of the formula wherein R R and R are each independently selected from the group consisting of hydrogen, alkyl, alkenyl and hydroxyalkyl each having a maximum of 4 carbon atoms; and n is the valence of M.

8. Method of claim 7 wherein the compound is calcium 1-(p-nitrobenzenesulfonyl)isourea.

9. Method of claim 7 wherein the compound is calcium 1- (p-aminobenzenesulfonyl isourea.

10. Method of claim 7 wherein the compound is calcium 1-(p-chlorobenzenes'ulfonyl)isourea.

11. Method of claim 7 wherein the compound is the ethanolamine salt of p-nitrobenzenesulfonyl isourea.

12. Method of claim 7 wherein the compound is potassium 1-(p-bromobenzenesulfonyl)isourea.

References Cited UNITED STATES PATENTS 3,307,932 3/1967 Guyot 7185 FOREIGN PATENTS 634,962 l/1963 Belgium.

JAMES O. THOMAS, 111., Primary Examiner