Process for increasing sugar yield in sugar cane
United States Patent [1 1 [111 3,874,872  
 Kupelian Apr. 1, 1975 PROCESS FOR INCREASING SUGAR YIELD [56] References Cited IN SUGAR CANE UNITED STATES PATENTS [75] Inventor: Robert Howard Kupelian, Yardley. 3,556,762 1/1971 Humm 71/86 Pa, 3.619.166 11/1971 Qucbcdeaux. Jr. 71/86 [73] Assignee: Amerlcan Cyanamid Company Prinmr Examiner-James 0. Thomas. Jr.  
 Stumlord, Conn.  
 Attorney. Agent, or FirmHarry H. Kline [22] Filed: Mar. 2, 1973 21 Appl. No.: 337,327 [57] ABSTRACT There is provided a novel method for increasing sucrose yield in sugar cane by treating sugar cane a few [5 }LS.CCI. 71/86 weeks prior to harvest with a polyulkylene glycol ester {2 gz&#39; of oz-hydroxy, B,B,B-trichloroethanephosphonic acid.  
 5 Claims, N0 Drawings PROCESS FOR INCREASING SUGAR YIELD IN SUGAR CANE The present invention relates to a novel method for increasing the sucrose yield of sugar cane by applying 5 H thereto an effective amount of a poly-alkylene glycol ester or mixture of esters of u-hydroxy where Ii is an integer from O to 3: and B,B,B-trichloroethanephosphonic acid having the for- 3. His-polypropylene glycol bis-a-hydrosy-3.3.3- mula: trichloroethane-diphosphonate having the structure:  
 sport neon H OH col from each of which the two hydroxyl groups have been removed. It is an integer from O to 3 and m is an integer of l to 3. or higher. CHOH OH It is known that sugar yields can be increased by L modifying the physiological process of sugar cane. C1 C1 However. none of the presently employed quaternary where I is 3 fi 3 G 3 and amines or ammomum halides as CXClTlPlillCd in US. v 4 a 2 l Pat. Nos. 3.493.361 and 3.660.072 is entirely satisfacand i from 0 to i mixtures thereof.  
 The active phosphonate or phosphonate mixture is preferably applied to cane stalks as a liquid spray. i.e..  
 wherein R R and R are residues of polyalkylene glyg 20 R OC H OC H O) 0 11 0 i-R tory as enhancing increased yields. If a class of compounds could be provided which would enhance yield activity ofsugar cane. such would fulfill a long felt need in the ML an aqueous solution or suspension prepared from a According to the process olthe invention, it has been wcmlhlc fl f 0r cmfllsmflblc conccmmtc m found that certain polyulkylunc glycul esters of amount sufficient to provide from about 1.0 pound per phahydroxy beta. beta. beta-triehloroethanephosphosacre to P of the &#34;wuvc phonic acid are unexpectedly highly effective for in- Hllwclfcrjslncc h phosphmwtcs chlphlycdilhlhc P creasing sucrose yield in field grown sugar cane. particcuss 0t thls mvcnltmh are generally hquldsh ulufly when they are dpplicd m thc youngcr growing may also be applied to cane stalks either as neat or disparts of the ripening cane stalks about tw t ten weeks solved in a small amount of solvent utilizing the ultra bet-Om hdrvcst low volume or low volume technique of application. In The phosphonates employed in the practice of the 40 hhphchhmlsthe phhsphlhhtc ls p instant invention are known. These are defined with P the lcchhlchl hlhtcrhll in thc form of discl&#39;cct particularly in the patent to Friedman. US. Pat. No. droplets having muss mcdhm dhlmctcr hclwcc&#34; 25 3 3 06 issued on Apt 2 19 4 which is incomoand 150 microns. Low volume application is similar to rated by reference herein. Illustrative of the useful low Volume hpphcmhlh cxccptlhg that the active cumpounds phosphonic i 2 2 2 phosphonate is dissolved in a minor amount. generally hydroxyethyl)-bis-[ 2-( 2-hydroxypropoxy)-lfrom about 5% to about by volume. of a relatively methylethyl] ester; phosphonic acid, (2,2,2-trichlo nonvolatile solvent. such as xylene. Panasol AN-2. Esso l-hydrnxyethyl )-bi5-[2-( Z-hydruxycthyoxy) ethyl] c3- HAN, 01&#39; Light Cycle Oil. and i8 applied US such in thC ter; phosphonic acid. (2.2.2-trichloro-l-hydroxyethyl form of discreet droplets having a mass median diame- 2-(2-hydroxypropoxy)-l-methylethyl ester. diester 5O ter of 25 to I50 I microns. Advantageously. the phoswith 1.1 &#39;-oxydi-2-propanol; phosphonic acid. (2.2.2- phonates employed in the process of the present inventriehloro-l -hydroxyethyl)-. 2-(2-hydroxyethoxy) ethyl tion can also be applied as aerosols or fogs using eonester. diester with diethylene glycol; and a compound ventional formulations and equipment. selected from the group consisting of: In general. wettablc powders are prepared bydisl. tris-polycthylene glycol bis-a-hydroxy-Bfifisolving the phosphonate in a volatile solvent, such as trichloroethane diphosphonate having the structure: acetone or methylene chloride, and spraying the thus il l where R is OC H (OC. ,H O),,, C. ,H OH and n formed solution on a finely divided carrier such as attaand :2 each represent an integer from 0. l. 2 or 3: clay. kaolin. talc, or diatomaceous earth and admixing 2. bis-polypropropylene glycol a-hydroxy-Bfifitherewith from about 1&#39;71 to 10% by weight of a surfactrichloroethanephosphonate having the structure: tant. A small amount of a dispersing agent. such as sodium lignosult&#39;omttc. may also be added. Surfactants which may be used include: polyoxyethylene sorbitan fatty acid esters. polyoxycthylene sorbitol esters and alkyl phenoxy polyoxyethylene ethanol. lt is a good practice to disperse the aforementioned wettable powder in water and then apply the same to sugar cane stalks in an amount sufficient to provide from about 0.5 pound to about 8.0 pounds per acre of the phosphonate.  
  An alternative manner in which to utilize the active compounds of the present invention is as an emulsifiablc concentrate. This is about 25% to 40% by weight of the phosphonate in about 5071 to 65% by weight of a solvent. such as xylene and admixing therewith about 571 to l()/( by weight of an emulsifier, such as a polyoxyethylated nonylphenol or a polyoxyethylene derivative ot an aliphatic or aromatic hydroxy compound. The thus prepared concentrate is then generally dispersed in water for application as a liquid spray.  
  The present invention will be further illustrated. but not limited. by the following example. Unless otherwise stated. the parts are by weight. I  
 EXAMPLE 1 The following procedure is used to determine the efficacy of test compounds for increasing sucrose yield in sugar cane.  
  An acetone: water l :l solution of the active ingredient is applied to 10 field grown sugar cane plants at a rate equivalent to 4 pounds per acre. At 4 weeks lst Harvest) and 5 weeks (2nd Harvest) after application ofthc compound designated in the table below. 5 of the plants are harvested. aggregated and a random sample removed for sugar analysis. The analytical methods for sugar content determination have been published. See. for instance. Tanimoto. The Press Mel/d ofCum&#39; Analysis. Hawaiian Planters; Record 57(2): 1 33 1964). The data is presented in Table l below.  
  Similar results are obtained when phosphonic acid. (2.2.2-trichlorol -hydroxyethyl )-his-[ 2-( 2- hydroxyethoxy) ethyl] ester; phosphonic acid. trichlorol -hydroxycthyl Z-t Z-hydroxypropoxy l methylethyl ester. diester with l.l&#39;-oxydi-Z-propanol; or phosphonic acid. t2.2.2-trichloro-l-hydroxycthyl)-. 2-(Z-hydroxyethoxy) ethyl ester. diester with diethylene glycol. is applied to field grown sugar cane at a rate equivalcntto 4 pounds per acre Sto 8 weeks before harvest.  
 I claim:  
 I. A method for increasing sugar yield in field grown.  
 ripening sugar cane comprising the step of: applying to said sugar cane about 2 to ll) weeks prior to harvest at a rate equivalent to form about 1 pound per acre to.  
 about lt) pounds per acre of the compound:  
 a. phosphonic acid. (2.2.2trichlorol hydroxyethyl )-bis-[ 2-( 2-hydroxypropoxy )-l methylethyl] ester;  
  phosphonic acid. (2.2.2-trichlorol hydroxyethyl bis-l 2-( Z-hydroxyethoxy )cthyl] es ter;  
 0 d 1st Harvest: 2nd Harvest w pol% Juice po1% Juice cane nuritv cane nuritv (HO-ZCH -o-cH CH-O) E-IHCCl 10.0 781 Untreated Control 6.2 65.5  
  i (HO-ZHCH -O-CH -H-O) a imal 12.33 81 .29 11 .65 7 .6  
 Untreated Control 9.16 753 9.65 78 .61  
 In the above table pol71 cane is a polarimetric determination and equals the percentage of sucrose. it it is the only substance in the solution which will rotate the plane of polarized light. The determination of p017! cane&#34; is a standard method for determining sucrose content of sugar cane and is accepted by the industry.  
  From the data provided above. it can be seen that the test compound. representative of its class as described above, is highly effective for increasing sucrose yield in cnnur nunn 4. The method according to claim 1 wherein the compound is phosphonic acid. (2.2,2-trichloro-lhydroxyethyl 2-( Z-hydroxypropoxy l -methylethyl ester. diester with l.l -oxydi-2-propanol.  
  5. The method according to claim I wherein the compound is phosphonic acid. (2,2.2-trichloro-lhydroxyethyl)-. 2-(2-hydroxyethoxy)ethyl ethyl ester. diester with diethylene glycol.