US3253904A

US3253904A - Composition and method for desuckering tobacco

Info

Publication number: US3253904A
Application number: US440015A
Authority: US
Inventors: Harrison Jean Bradley
Original assignee: EI Du Pont de Nemours and Co
Current assignee: EIDP Inc
Priority date: 1965-03-15
Filing date: 1965-03-15
Publication date: 1966-05-31
Anticipated expiration: 1983-05-31

Description

United States Patent 3,253,904 COMPOSITION AND METHOD FOR DESUCKERING TOBACCO Jean Bradley Harrison, Niagara Falls, N.Y., assignor to E. I. du Pont de Nemours and Company, Wilmington, Del., a corporation of Delaware No Drawing. Filed Mar. 15, 1965, Ser. No. 440,015 11 Claims. (Cl. 712.6)

This application is a continuation-in-part of my copending application Serial No. 236,149, filed November 7, 1962; which in turn is a continuation-in-p'art of my application Serial No. 139,595, filed September 21, 1961, both now abandoned.

This invention relates to methods for the chemical treatment of tobacco plants. More specifically, it relates to the treatment of tobacco plants in the topping stage with compositions of esters of carbanilic acids for the purpose of controlling axillary bud growth.

Sucker growth, a term given for axillary bud growth, is an age-old problem in the tobacco industry. It dates back to the growers realization that good quality smoking tobacco leaf contains a high amount of sugar and that axillary buds on tobacco plants use this sugar for growth.

The farmers problem, therefore, has been to eliminate I sucker growth economically and without any harmful side effects to the desirable tobacco leaf. Heretofore, chemical substances have been known to decrease sucker growth in tobacco plants, but with undesirable side efiects to the tobacco leaves.

The compounds used in this invention overcome this problem when sprayed on tobacco plants in the topping stage by preventing or markedly inhibiting the growth of suckers and decreasing the loss of leaf sugar without adversely affecting the leaves of the plant. The result is an increase in the amount of high quality smoking tobacco leaf.

My invention is the treating of tobacco plants in a crucial point of their development, namely in the topping stage, with a compound having the following general formula:

wherein X, Y and Z are the same or different and are each chlorine, bromine, fluorine, alkyl of 1 through 4 carbon atoms and alkoxy of 1 through 4 carbon atoms;

m, n and t are each 0 or 1';

R is vinyl, methylvinyl, chloromethylvinyl, hydroxymethylvinyl, ethynyl, methylethynyl, hydroxymethylethynyl, chloromethylethynyl, l-hydroxyalkyl, l-chloroalkyl and l-bromoalkyl where the alkyl group is 1 through 4 carbon atoms and CH Q;

Q is hydrogen, chlorine, bromine, hydroxy, alkyl, monochloroalkyl, monobromoalkyl, hydroxyalkyl, and m'ethoxyalkyl where the alkyl is 1 through 4 carbon atoms, alkoXy of 1 through 4 carbon atoms, alkoxyalkyl, alkenyl, chloralkenyl, bromoalkenyl and alkynyl of 2 through 4 carbon atoms, hydroxyalkenyl, hydroXyalkynyl, chloroalkynyl and bromoalkynyl of 3 through 4 carbon atoms and alkoxyalkenyl and alkoxyalkynyl of 3 through 6 carbon atoms; and

R is hydrogen, chlorine, bromine, alkyl, monochloroalkyl,

ice

monobromoalkyl, hydroxyalkyl, and methoxyalkyl where the alkyl is 1 through 4 carbon atoms, alkoxy of 1 through 4 carbon atoms, alkoxyalkyl, alkenyl, chloroalkenyl, bromoalkenyl and alkynyl of 2 through 4 carbon atoms, hydroxyalkenyl, hydroxyalkynyl, chloroalkynyl and bromoalkynyl of 3 through 4 carbon atoms and alkoxyalkenyl and alkoxyalkynyl of 3 through 6 carbon atoms with the limitation that R and R cannot both be an ethylenic or acetylenic unsaturation at the same time, and at least one of m, n and tmust be 1.

Although all the compounds within this application are preferred, particularly preferred compounds because of their outstanding activity in reducing sucker growth at low rates are those of the formula:

wherein X and Y are chloro or methyl;

m is 0 or 1;

R is hydrogen, methyl, ethyl, methoxymethyl, chloromethyl, l-chloroethyl, alkenyl of C -C or alkynyl of C -C and- Q is hydrogen or chlorine.

It is customary in the tobacco raising industry to break out the main stem by hand when to of the tobacco plants are in flower. This operation is called topping.

Generally, compounds used in this invention are applied to tobacco plants during the topping stage. Specifically, the compounds used in this invention are applied during the period of seven days before to four days after topping in an amount of active compound sufficient to inhibit sucker growth. Conveniently, they are applied by spraying in emulsions or powder suspensions in water. Ordinarily, application at the rate of 0.125 to 6 and preferably 2 to 5 pounds active ingredient per acre will be used. By treating tobacco plants in the above manner particularly outstanding results are achieved. Sucker growth on tobacco plants is inhibited without injury to the remainder of the tobacco plant. The net result is a larger yield of good quality smoking tobacco.

Compositions of this invention are prepared in a manner similar to the compositions described in Luckenbaugh US. Patent 2,935,393 issued May 3, 1960. The Luckenbaugh patent is herein incorporated by reference. The compositions, therefore, will contain the active agent combined with a surfactant and either an emulsifiable oil to provide a liquid media or an inert solid diluent to provide a powder form of the composition.

Additional surfactant can be added to the above formulation to increase the ratio of surfactantzactive agent up to as high as 20:1 by weight. Particularly preferred compositions contain 0.25 :1 to 5:1, surfiaotanmaotive agent by weight.

A particularly preferred composition because of its persistency on the plant and ease of dispersion is one containing 2 to 15% by weight of diethanolamine, tri ethanolamine, di-isopropanolamine or tri-isopropanolamine, 6 to 35% by weight of dodecylbenzenesulfonic acid, 30 to 60% by weight of isophorone and- 10 to 30% by weight of m-chlorocarbanilic acid, isopropyl ester or m-chlorocarbanilic acid, ester with 1,3-dichloro-2-propanol.

The compounds of this invention are prepared by methillustrated below.

Route 1, the reaction of an aromatic amine (A) with an alkyl haloformate (B) in the presence of an acid acceptor to form a carbanilate is well known to the art. The acid acceptor may be a second equivalent of the aromatic amine (Hentschel, Ber. 18, 978), pyridine (Chattaway, J. Chem. Soc., 117, 710), tertiary aliphatic organic bases such as triethylamine, as well as inorganic bases such as sodium bicarbonate, sodium carbonate (Schmidt, Ph. Ch., 58, 516) or sodium hydroxide (Brit. 780,713/57). The reaction can be run in the absence of solvent, in indifferent organic solvents (benzene, xylene, ether, petroleum, etc.), or in water (Brit. 780,713/57; Can. 522,141/56; W. J. Hickinbottom, Reactions of Organic Compounds, Longmans, Green and Co., 3rd ed., 1957, p. 403). Reaction temperatures may be from 20. to 100 with a preferred range of to 30. During the course of the reaction the acid acceptor forms an acid acceptor hydrohalide.

. Km 7 @mn +hal. o-o-e HCH2Q acid acceptor Yn R Xm fl V NHCO(|J H-CHz-Q acid acceptor hydrohalide Y. R

If the reaction is run in a solvent such as xylene, the acid acceptor hydrohalide generally precipitates and may be removed by filtration. Evaporation of the filtrate yields essentially pure product.

This product may be either a liquid or a solid at room temperature. If a solid it may generally be recrystallized. If a liquid it may generally be distilled under reduced pressure.

The haloformates (B) are prepared by Well-known literature procedures (for example, the reaction of phosgene plus an alcohol). Where Q equals Cl, it is con- 4 venient to prepare the haloformate from phosgene plus 0 ll ll C1OO1+RCHOHZ OlC-O(|3HCH:C1

are not obtained. The yield, however of in the method of Jones was markedly reduced by the pronounced tendency of the formed chloroformate to react with a second equivalent of epoxide with the formation of the symmetrical carbonate. US. 2,820,810 describes the reverse addition whereby the epoxide is added to liquid phosgene containing a catalytic amount of hydrogen halide. Under these conditions the reverse addition results in high yields of chloroformate. We have found that by the reverse addition of an epoxide to phosgene containing pyridine as a catalyst high yields of chloroformate are obtained.

Route II, the reaction of an aromatic isocyanate (C) with. an alcohol (D) to form a carbanilate is well known to the art [Saunders, Chem. Rev.,43, 203 (1948); Gumpert, I. Prakt. Chem., 31, 119 (1885); Gumpert, I. Prakt. Chem., 32, 278 (1885); Knoevenagel, Ann., 297, 148 (1897)]. The reaction may be run in the absence of solvents or in the presence of indifferent solvents (benzene, xylene, petroleum ether, ethyl ether, etc.) and at temperatures ranging from 0 to These reactions may be non-catalyzed [Baker, J. Chem. Soc., 1947, 713; Dyer, J. Am. Chem. Soc., 71, 4106 (1949)] or catalyzed by any of a number of basic catalysts, for example tertiary amines [Saunders, Chem. Rev., 43, 203 (1948)], triethylamine [Burrus, J. Am. Chem. Soc., 80, 5948 (1950)], diethyl aniline (Baker, locus cit.), or pyridine (Baker, locus cit.).

This invention will be better understood by referring to the following illustrative examples. All percentages are by weight unless otherwise stated.

Example 1 m-Chlorocarbanilic acid, ester with 1,3-dichloropropanol-2 is formulated according to the following recipe:

Percent m-Chlorocarbanilic acid, ester with 1,3-dichloropropanol-2 35 Commercial mixture of ethylenediamine salt of do- -decylbenzene sulfonic acid and polyoxyethylene sorbitan monotallate (Atlox 4600) 35 Isophorone 30 Example 2 Another method of formulating and using m-chlorocarhanilic acid, ester with 1,3-dichloropropanol-2 is as follows:

lPercen-t m-Chlorocarbanilic acid, ester with 1,3-dichloropropanol-2 20 Isooctylphenylpolyethoxyethanol (Triton X100) 20 Sodium lignin sulfonate 4 Hydrated attapulgite clay -n 2.5 Water 53.5

The compound, 2,5-dichlorocarbanilic acid, ester with 1,3-dichloro-2-propanol, may be formulated and used as the following recipe:

Percent 2,5-dichlorocarbanilic acid, ester with 1,3-dichloro- 2-propanol 30 Polyoxyethylene sorbitan monolaurate (Tween 20) 30 Cyclohexanone 40 The above components are mutually soluble when mixed together.

This formulation is used at the rate of two pounds of active ingredient per acre for the control of tobacco suckers as described in Example 1.

Example 4 2,5-dichlorocarbanilic acid, ester with 1,3-dichloro-2- propanol is also used on tobacco when formulated in the following manner:

Percent 2,5-dichlorocarbanilic acid, ester with 1,3-dichloropropanol-2 30 Sodium lauryl sulfate 30 Attapulgite clay 40 A wet-table powder is prepared from the above components by blending and micropulverizing.

When used at the rate of two to four pounds per acre of active ingredient in 60 gallons of water at topping time, excellent sucker control for an extended period is obtained on flue-cured tobacco.

Example 5 When m-chlorocarhanilic acid, ester with l-chloro-Z- propanol is blended with the formulating ingredients shown, it is useful for controlling tobacco suckers as described.

Percent m-Chlorocarbanilic acid, ester with 1-chloro-2- propanol 35 Isooctylphenylpolyethoxyethanol (Triton X-lOO) 35 Isophorone 30 When mixed together, these components form a clear solution which may readily be emulsified in water.

This formulation is used according to the technique of Example 1 to control sucker growth of topped tobacco plants.

Example 6 When o-chlorocarbanilic acid, ester with 1,3-dichloro- 2-propanol is formulated according to the following recipe, it may be used as described below.

Percent o-Chlorocarbanilic acid, ester with l,3-dichloro-2 propanol 20 Trimethylnonylether of polyethylene glycol 20 Cyclohexanone 60 These components are mutually soluble to form a clear solution which emulsifies readily in water.

The above formulation is applied in 60 gallons of water at the rate of two pounds of active ingredient per acre to air-cured tobacco before or after topping. Excellent sucker control is noted during the harvest season without apparent injury to the tobacco plants.

Example 7 The formulation and use of m-chlorocarbanilic acid, ester with 2-chloroethanol is as follows:

Percent In chlorocarbanilic acid, ester with 2 chloroethanol 35 Commercial mixture of the ethylenediamine salt of dodecylbenzenesulfonic acid and polyoxyethylene sorbitan monotallate (Atlox 4600) 20 Isophorone 45 When mixed, the above components yield a clear solution which readily emulsifies in water.

When used at the rate of 3 pounds per gallon of active ingredient in 60 gallons of water at topping time, excellent sucker control for an extended period is obtained on flue-cured tobacco.

Example 8 The formulation and use of m-chlorocarbanilic acid, ester with isopropanol for control of tobacco suckers is illustrated below.

Percent m-Chlorocarbanilic acid, ester with propanol-2 35 Polyethoxynonylphenol 20 Dibutylketone 45 An emulsifiable solution is prepared by mixing together the above components.

This formulation is applied at .the rate of 1 to 2 pounds of active ingredient per acre to control suckers on tobacco plants according to the methods of Example 1.

Example 9 m-Chlorocarbanilic acid, sec-butyl ester is formulated and used in the following manner:

Percent m-Chlorocarbanilic acid, sec-butyl ester 35 Sodium dodecylbenzene sulfonate 20 Synthetic fine silica 45 Blending and micropulverizing the above components gives a wettable powder which disperses readily in Water. This formulation is used at the rate of 2 pounds of active ingredient per acre as described in Example 4.

Example 10 2,5-dichlorocarbanilic acid, isopropyl ester is formulated and used as follows:

Percent 2,5-dichlorocarbanilic acid, isopropyl ester 30 Polyoxyethylated tall oil 15 Z-heptanone 55 A homogeneous, emulsifiable solution is prepared by mixing together the above components.

The above formulation is used at the rate of 2 pounds of active ingredient per acre in 60 gallons of water for the control of tobacco suckers. Application is made when the tobacco is topped. Good sucker control is obtained.

7 Example 11 The compound, m-chlorocarbanilic acid, ester with 1- chloro-2-propanol is used and formulated as follows:

' Percent m-Chlorocarbanilic acid, ester with 1-chloro-2-propanol 40 Dioctyl sodium sulfosuccinate condensed 85-15 with sodiumbenzoate (AerosoP OTB) 15 Attapulgite clay 45 The above wettable powder is prepared by blending and micropulverizing the components to a particle size below 50 microns.

This formulation is used for control of suckers on tobacco grown for cigar production. An application of two pounds of active ingredient per acre applied 'at or near the topping stage gives satisfactory control of suckers during the harvest period.

Example 12 m-Chlorocarbanilic acid, ester with isopropanol is formulated as follows:

Percent m-Chlorocarbanilic acid, ester with isopropanol 20 Isooctylphenylpolyethoxyethanol (Triton X- 100) 20 Sodium lignin sulfonate 4 Hydrated attapulgite clay 2.5 Water 53.5

The above ingredients except the isooctylphenylpolyethoxyethanol are mixed together and sand milled until the active component has a particle size of microns or less. After milling, the isooctylphenylpolyethoxyethanol is added With mild stirring.

This formulation is used for the control of tobacco sucker according to the procedure of Example 2.

Example 13 2,5-dichlorocarbanilic acid, sec-butyl ester is formulated as follows:

Percent 2,5-dichlorocarbanilic acid, sec-butyl ester 30 Polyoxyethylene sorbitan monolaurate (Tween 20) 30 Cyclohexanone 40 The above components are mutually soluble when mixed together.

This formulation is used at the rate of two pounds of active ingredient per acre for the control of tobacco suckers according to the procedures of Example 14.

Example 14 The above homogeneous solution is prepared by simple mixing of the mutually soluble components.

This formulation is applied at the rate of two pounds of active ingredient per acre in 40 to 100 gallons of water per acre to tobacco before or after topping. Excellent control of suckers (axillary buds) is obtained over a period of 40 days. Control of the suckers results in in- -creased yield of tobacco leaves.

Example 15 Percent m-Chlorocarbanilic acid, ester with 1,3-dichloro-2- propanol 25 Triethanolamine 10 Dodecylbenzenesulfonic acid Isophorone 45 The m-chlorocarbanilic acid, ester with 1,3-dichloro- 2-propanol and triethanolamine are dissolved in the solvent isophorone. The dodecylbenzenesulfonic acid is then added slowly with cooling.

Since the acid strength of different lots of dodecylbenzenesulfonic acid may vary, it is necessary prior to formulation to determine by titration the amount of triethanolamine required to neutralize the dodecylbenzenesulfonic acid being used so as to obtain a mixture which is neither excessively acidic nor excessively alkaline. If

desired, xylene, toluene or other alkylated benzenes canbe substituted for part of the isophorone.

The above formulation is applied at the rate of 1 to 2 pounds per acre of active ingredient to the leaves of tobacco plants such as flue-cured and burley types. These plants are topped when approximately are in flower. The application is made with'the active emulsified in 40-' 60 gallons of water. The water acts as a carrier and as a means to facilitate contact of the active material with most of the leaves on each treated plant. This treatment gives long-lasting sucker control on tobacco plants topped just prior or immediately after treatment. An increase in the yield of tobacco leaf is noted.

Example 16 Percent m-Chlorocarbanilic acid, ester with 1-methoxy-2 propanol 20.0 Triisopropanolamine 6.2 Dodecylbenzenesulfonic acid 13.8 Isophorone 60.0

The m-chlorocarbanilic acid, ester with 1-methoxy-2- propanol and the triisopropanolamine are dissolved in the isophorone. The dodecylbenzenesulfonic acid is slowly added to this mixture with cooling. If desired, tolene, xylene, or other alkylated benzenes can be substituted for part of the isophorone.

This material is applied as a foliar spray to tobacco plants topped when 90% of the plants are in flower. By applying 1.5 pounds per acre of active ingredient in gallons of water, the spray contacts most of the leaves on each treated plant. This treatment inhibits the growth of tobacco suckers and increases the yield of smoking leaf.

Example 17 7 Percent m-Chlorocarbanilic acid, ester with 3-chlo'ro-2- butanol 30.0 Dodecyl'benzenesulfonic acid 24.1 Diisopropanolamine 11.8 Isophorone 34.1

The m-.chlorocarbanilic acid, ester with 3-chloro-2- butanol and the diisopropanolamine are dissolved in the isophorone. The dodecylbenzenesulfonic acid is slowly added to the mixture while cooling.

This compound is applied as a foliar spray at the rate of 2 to 3 pounds of active ingredient per acre in 50 gallons of water during the time that approximately 90% of the tobacco plants are in flower. Care is used to secure adequate coverage of tobacco foliage. The tobacco plants are topped the following day. The growth of tobacco suckers is prevented by this treatment. The yield of tobacco is increased.

Example 18 Percent m Chlorocarbanilic acid, ester with isopropanol 36.0 Diethanolamine 2.5 Dodecylbenzenesulfonic acid 6.5 Xylene 55.0

The m-chlorocarbanilic acid, ester with isopropanol and the diethanolamine are dissolved in the xylene. The dodecylbenzenesulfonic acid is added slowly to the mixture. A cooling bath is employed to remove the heat of neutralization. Triethanolamine at 3.3% can replace the diethanolamine in this formulation. The percent of xylene used is adjusted to correct for the increase in amine content.

The above composition is applied as a foliar spray to properly topped tobacco at the rate of two pounds per acre of active ingredient in 40 gallons of Water. Treatment with this chemical effectively inhibits the growth of tobacco suckers and results in increased yields of tobacco.

Example 19 Percent m-Chlorocarbanilic acid, ester with 3-butyn-2-ol 15 Triethanolamine 15 Dodecylbenzenesulfonic acid 30 Isophorone 40 The m-chlorocarbanilic acid, ester with 3-butyn-2-ol and the triethanolamine are dissolved in the isophorone. 'I he dodecylbenzenesulfonic acid is slowly added to the mixture. A cooling bath is used to remove the heat of neutralization.

This formulation is applied as a foliar spray at the rate of 2 to 3 pounds per acre of active ingredient in an emulsion of 50 to 75 gallons of Water. Before spraying, the tobacco plants are topped when approximately 90% of the plants are in flower. This treatment prevents the growth of the axillary buds on tobacco plants and results in an increased yield of tobacco leaf.

Example 20 Percent 2,5-dichlorcarbanilic acid, ester with 3-butyn-1-ol 15 Dodecylbenzenesulfonic acid, sodium salt 75 Synthetic fine silica The active ingredient, 2,5-dichlorocarbanilic acid, ester with 3-butyn-l-ol is ground in a hammer mill until its particle size is substantially less than 30 microns. Following the grinding, all of the ingredients are thoroughly blended in a ribbon blender.

This wettable powder formulation is applied at the rate of 4 pounds per acre of active ingredient in 50 to 75 gallons of water. When this suspension is applied as a foliar spray to topped tobacco, the growth of suckers is prevented. This inhibition of sucker growth results in increased yields of smoking leaf.

Example 21 Percent 2,5-dichlorocarbanilic acid, ester with 4-ethoxy-4- penten-l-ol 50.0 Dodecylbenzenesulfonic acid, potassium salt 12.5 Partially desulfonated sodium lignin sulfonates 0.5 Kaolinitic clay 37.0

All of the above ingredients are thoroughly blended and ground in a hammer mill until the particle size is essentially less than 30 microns.

A slurry is made 'by mixing 8 pounds of this wettable powder with a small quantity of water. The slurry is then diluted to 75 gallons with water. The mixture is applied as a foliar spray on one acre of topped tobacco. Care is used to keep the powder suspended and to obtain good coverage of the foliage. This treatment gives good sucker control on topped tobacco.

Example 22 Percent m-Chlorocarbanilic acid, ester with 6-chloro-4- hep-ten-Z-ol 40.0 Dodecylbenzenesulfonic acid, sodium salt 40.0 Partially desulfonated sodium lignin sulfonate 0.5 Kaolinitic clay 19.5

All of the ingredients are thoroughly blended together and ground in a hammer mill or other grinding equipment until the particle size is essentially less than 30 microns.

Sixteen pounds of this material is suspended in 100 to 150 gallons of water and the suspension is sprayed on two acres of tobacco. The tobacco is topped immediately following application. This foliar treatment gives good inhibition of the growth of suckers.

Example 23 Percent m-C-hlorocarbanilic acid, ester with 1,2-propanediol 25 Blend of polyalcoholcarboxylic acid ester and sulfonated oils 6 Isophorone 69 The m-chlorocarbanilic acid, ester with 1,-2-propanediol and the emulsifier, blend of polyalcoholcarboxylic acid esters and sulfonated oils, are dissolved in the isophorone.

Four pounds of the active material formulated as indicated above are emulsified in 'gallons of water. Five pounds of the triethanolamine salt of dodecylbenzenesulfonic acid are added to this mixture and dissolved by agitation. This mixture is applied as a foliar spray on an acre of topped tobacco. The growth of tobacco suckers is inhibited by the treatment.

Example 24 Percent 2,5-dichlorocarbanilic acid, ester with 3-butyn-2-ol 20 Blend of alkylaryl sulfonates and nonylphenol polyoxyethylene condensation products Xylene 34 Isophorone 40 Example 25 Percent m-Chlorocarbanilic acid, ester with 1-chloro-3-buten- 2-01 30 Blend of alkylaryl sulfonates and nonylphenol polyoxylethylene condensation products Isophorone 6 2 The ingredients are stirred together until the solid is dissolved and the solution is uniform.

If desired, benzene, toluene or xylene can be substitute-d for part of the isophorone.

Five pounds of the diethanolamine, salt of dodecylbenzene sulfonic acid are dissolved in 50 to 75 gallons of water. Alternatively, a like amount by weight of the triethanolamide salt can be used. Eight pounds of the above formulation are emulsified in the water solution and the emulsion sprayed as a foliar treatment on an acre of topped tobacco. Good sucker control is obtained.

Example 26 Percent m-Chlorocarbanilic acid, ester with 1-chloro-3-buten- 2-01 25 Dodecylbenzenesulfonic acid 20 Triisopropanolamine 9 Isophorone 23 Xylene 23 The formulation is prepared by dissolving the m-chlorocarbanilic acid, ester with 1-chloro-3-buten-2-ol and the triisopropanolamine in the isophorone and xylene. The dodecylbenzenesulfonic acid is slowly added with cooling.

Three pound-s of active ingredient in the above formulation are emulsified in 40, to 60 gallons of water and applied by foliar spray to topped tobacco. The treatment inhibits the growth of tobacco suckers during the harvest period.

Example 27 Percent m-Chlorocar-banilic acid, ester with isopropanol 25 Dodecylbenzenesulfonic acid Triethanolamine 10 Xylene 45 The m-chlorocarbanilic acid ester with isopropanol, triethanolamine and xylene are thoroughly mixed and the Example 28 Percent m-Chlorocarbanilic acid, ester with 1-chloro-2-propanol 30.0 Dodecylbenzenesulfonic acid 15.0 Triisopropanolamine 13.2 Isophorone 41.8

The m-chlorocarbanilic acid, ester with 1-chloro-2-propanol and the triisopropanolamine are dissolved in the isophorone. The dodecylbenzenesulfonic acid is added slowly with cooling.

Two to four pounds of active ingredient in the'above formulation is emulsified in 50-75 gallons of water and sprayed on an acre of tobacco such as flue-cured, burley, or dark air cured types. The tobacco is topped within 36 hours after treatment. This treatment prevents the growth of tobacco suckers and increases the yield of tobacco leaf.

Example 29 Percent m-Chlorocarbanilic acid, ester with 1-hexyn-3-ol Dodecylbenzenesulfonic acid 20 I Diethanolamine 6 Toluene 2O Isophorone 29 The m-chlorocarbanilic acid, ester with l-hexyn-3-ol and the diethanolamine are dissolved in the toluene and isophorone. The dodecylbenzenesulfonic acid is added slowly with cooling.

From 10 to 24 pounds of this formulation are added to 50 to 100 gallons of water and applied to an acre of topped tobacco, using care to obtain good coverage of the leaves. The treatment effectively inhibits the growth of suckers on the topped tobacco.

Examples -150 The following compounds are each substituted one at a time for the m-chlorocarbanilic acid, ester with 1,3-dich1oro-2-propanol of Example 15 in like amount by weight and are formulated in like manner. Like results are achieved.

30. m-Chlorocarbanilic acid, isopropyl ester 31. o-Chlorocarbanilic acid, isopropyl ester 32. 2,5-dichlorocarbanilic acid, sec-'butyl ester 33. 2,3,S-trichlorocarbanilic acid, ethyl ester 34. m-Chlorocarbanilic acid, ester with l-chloro-Z- propanol 35. m-Methylcarbanilic acid, ester with 1,3-dich1oro-2- propanol .36. .2,5-dichlorocarbanilic acid, ester with 1,3-dich1oro- 2-propanol 37. o-Chlorocarbanilic acid, ester with 1,3-dichloro- Z-pro'panol 38. p-Chlorocarbanilic acid, amyl ester 39. m-Bromocarbanilic acid, isopropyl ester 40. m-Chlorocarbanilic acid, ester with l-methoxy- Z-hydroxy-propane 41. m-Fluorocarbanilic acid, isopropyl ester 42. m-Fluorocarbanilic acid, ester with 1,3-dichloro- 2-propanol 43. 2,5-dichlorocarbanilic acid, methoxyethyl ester 44. m-Chlorocar-banilic acid, :beta-chloroethyl ester 45. o-Chlorocar-banilic acid, ester with 1,3-dimethoxy- 2-propanol 46. m-Chlorocarbanilic acid, ester with l-bromo- 2-propanol 47. m-Chlorocarbanilic acid, ester with 1,4-diisopropoxy-S-hexyn-Z-ol 48. m-Methylcarbanilic acid, isopropyl ester 49. m-Butylcarbanilic acid, 2-chloroethyl ester 50. 2--meth0xy-5-chlorocarbanilic acid, sec-amyl ester 51. 4-n-butoxy carbanilic acid, ester with 1,3-dichloro- 2-prop-anol 52. 2,5-dichlorocarbanilic acid, ester with l-methoxy- 2-propanol 53. 2,3-dichloro-5-methy1carbanilic acid, isopropyl ester 54. 2-fiuoro-5-methylcarbanilic acid, beta-chloroethyl ester 55. m-Chlorocarbanilic acid, butoxyethyl ester 56. m-Bromocarbanilic acid, ester with 1-chloro-3- methoxy-Z-propanol 57. m-Chlorocarbanilic acid, ester with 2-chloroethanol 58. m-Chlorocarbanilic acid, ester with 1-bromo-3-chlor0- 2-propano1 59. o-Brornocarbanilic acid, ester with l-methoxy-Z- propanol 60. 2,3,6-trichlorocarbanilic acid, ester with 3-chloro-2- butanol 61. p-Chlorocarbanilic acid, ester with 1-chloro-3-met-hyl- Z-butanol 62. 2-methyl-5-chlorocarbanilic acid, ester with sec-amyl alcohol 63. 2,3,6-trichlo1'ocarbanilic acid, ester with 1,3-dichlor0- 2-propanol 64. Z-chloro-S-met-hylcarbanilic acid, ester with l-chloro- 2-propanol 65. 2-chloro-S-n-butylcarbanilic acid, ester with 1,3-

dichloro-2-propanol 66. m Chlorocarbanilic acid, ester with 1,3-dimethoxy- 2-propanol 67. m-Bromocarbanilic acid, 2-chloro-ethyl ester 68. m-Fluorocarbanilic acid, ester with 2-(n-butoxy) ethanol 69. p-Chlorocarbanilic acid, ester with l-ethoxy-Z- propanol 70. o-Chlorocarbanilic acid, ester with 3-pentanol 71. m-Chlorocarbanilic acid, ester with 3-methyl-2- butanol 72. 2,5-dichlorocarbanilic acid, isopropyl ester 73. m-Chlorocarbanilic acid, sec-butyl ester 74. m-Chlorocarbanilic acid, monoester with ethylene glycol 75. m-Chlorocarbanilic acid, monoester with 1,2-

propanediol 76. o-Chlorocarbanilic acid, ester with propargyl alcohol 77. m-Chlorocarbanilic acid, ester with allyl alcohol 78. 2,5-dichlorocarbanilic acid, ester with -allyl alcohol 79. 2,5-dichlorocarbanilic acid, ester with 3-butyn-2-ol 80. m-Chlorocarbanilic acid, ester with 1-chloro-3-buteno-Chlorocarbanilic acid, ester with methallylalcohol 2,5-dichlorocarbanilic acid, ester with S-butyn-l-ol m-Chlorocar-banilic acid, ester with 4-pentyn-2-ol o-Chlorocarbanilic acid, ester with 4-pentyn-2-ol 85. o-Chlorocarbanilic acid, ester with 1-pentyn-3-ol 86. m-Chlorocarbanilic acid, ester with 1-hexyn-3-ol 87. m-Chlorocarbanilic acid, monoester with 2-butyn-1,4-

diol

88. m-Chlorocarbanilic acid, ester with 4-chloro-2-butyn- 89. 2,5-dichlorocarbanilic acid, monoester with Z-butene- 1,4-dio1 90. rn-Chlorocarbanilic acid, ester with 4-chloro-2-butenl-ol 91. o-Chlorocarbanilic acid, ester with Z-butyn-l-ol 92. m-Chlorocarbanilic acid, ester withZ-chloro-lpropanol 93. m-Chloroc-arbanilic acid, monoester with 2,5-

hexanediol 94. 2,5-dichlorocarbanilic acid, ester with 3-methylene- 2-pentanol 95. o-Chlorocarbanilic acid, ester with 5chloro-3-penten- 96. rn-Chlorocarbanilie acid, ester with 4-chloro-3-buten- 97. rn-Chlorocarbanilic acid, rnonoester with 3-hexene- 2,5-diol 98. 2,5-dichlorocarbanilic acid, ester with 1,4-dimethoxy- S-hexyn-Z-ol 99. 2,5-dichlorocarbanilic acid, ester with 4-ethoxy-3- penten-1-ol 100. o-Chlorocarbanilic acid, ester with 1-bromo-3-hexyn- 101. m-Chlorocarbanilic acid, ester with 5-chloro-3- pentyn-Z-ol 102. m-Chlorocarbanilic acid, ester with 5-bromo-3- hexyn-2-ol 103. m-Chlorocarbanilic acid, 4-ester with 2-pentyn-1,4-o1

104. m-Chlorocarbanilic acid, monoester with 3-hexyn- 2,5-diol 105. m-Chlorocarbanilic acid, ester with 6-chlor0-4- hepten-Z-ol 106. o-Chlorocarbanilic acid, ester with l-chloroethanol 107. m-Chlorocarbanilic acid, ester with l-brornoethanol 108. 2,5-dichlorocarbanilic acid, l-ester with 1,2-

pentanediol 109; 2,5-dichlorocarbanilic acid, ester with 2-chloro-1- pentanol 110. o-Chlorocarbanilic acid, ester with 2-br omo-1- propanol 111. o-Chlorocarbanilic acid, ester with 2-br0mo-1- pentanol 112. m-Chlorocarbanilic acid, ester with 1-chl0r0-3- heptanol 113. m-Chlorocarbanilic acid, ester with 6-chloro-1- hexanol 114. 2,5-dichlorcarbanilic acid, ester with -chloro-2- hexanol 115. o-Chlorocarbanilic acid, ester with 1,4-dibromo-2- butanol 116. m-Chlorocarbanilic acid, 3-ester with 4-bromo-1,3-

heptanediol 117. m-Chlorocarbanilic acid, ester with 6-brorno-1- hexanol 118. 2,5-dichlorocarbanilic acid, ester with 1-methoxy-2- chloroethanol 119. rn-Chlorocarbanilic acid, ester with 1-butoXy-2- chloroethanol 120. o-Chlorocarbanilic acid, ester with l-isopropoxy-2- propanol 121. o-Chlorocarbanilic acid, monoester with 1,6-

hexanediol 122. rn-Chlorocarbanilic acid, ester with 4-chloro-3- buten-Z-ol 123. 2,5-dichlorocarbanilic acid, ester with 3-brorno-3,5-

hexadien-Z-ol 124. m-Chlorocarbanilic acid, 4-ester with l-hexene- 3,4-diol 1 4 125. 2,5-dichlorocarbanilic acid, ester with 3,5-hexadien- 2-01 126. o-Chlorocarbanilic acid, ester with 5-bromo-3-pentyl 2-ol 127. rn-Chlorocarbanilic acid, ester with 4-methoxy-3- buten-2-o1 128. m-Chlorocarbanilic acid, ester with 5-ethoXy-3- buten-2-0l 129. m-Chlorocarbanilic acid, ester with 4-methoxy-3- butyn-2-ol 130. m-Chlorocarbanilic acid, ester with 5-ethoxy-3- buten-Z-ol 131. m-Chlorocarbanilic acid, ester with 4-penten-2-ol 132. o-Chlorocarbanilic acid, ester with 5-rnethy1-5- hexen-Z-ol 133. m-Chlorocarbanilic acid, ester with 3-methoxy-1- propanol 134. m-Chlorocarbanilic acid, ester with 3-isopropoxy-1- propanol 135. 2,5-dichlorocarbanilic acid, ester with 4-chloro-3- lbuten-l-ol 136. 2,5-dichlorocarbanilic acid, ester with 6-chloro-4- heptyn-2-ol 137. o-Chlorocarbanilic acid, ester with 4-bromo-3- 13-8. o-Chlorocarbanilic acid, ester with 6-bromo-4-hepten-2-ol 139. rn-Chlorocarbanilic acid, ester with 3-heXyn-1-ol 140. m-Ohlorocarbanilic acid, 2-ester with 5-hexene-2,4-

diol

141. m-Chlorocarbanilic acid, monoester with S-hexen 1,6-diol 142. m-Chlorocarbanilic acid, l-ester with 3-pentyn-1,5-

diol

143. rn-Chlorocarbanilic acid, monoester with 3-hexyn- 1,6-diol 144. o-Chlorocarbanilic acid, ester with 5-chloro-3- pentyn-Z-ol 145. o-Chlorocarbanilic acid, ester with 5-bromo-3- pentyn-2-ol 146. 2,5-dichlorocarbanilic acid, ester with 6-brorno-4- heptyn-Z-ol 147. m-Chlorocarbanilic acid, ester with 5-meth0Xy-4- penten-2-ol 148. m-Chlorocarbanilic acid, ester with 4-isopropoxy- 3-penten-1-ol 149. m-Chlorocarbanilic acid, ester with 5-methoXy-4- pentyn-Z-ol The invention claimed is:

1. The method comprising applying a foliar spray to tobacco plants while the plants are-in the topping stage said spray comprising a desuckering amount of a compound of the formula:

Where monobromoalkyl, hydroxyalkyl, where each alkyl is 1 through 4 carbon atoms, alkoxy of 1 through 4 carbon atoms, alkoxyalkyl, alkenyl, chloroalkenyl, bromoalkenyl, and alkynyl of 2 through 4 carbon atoms, hydroxyalkenyl, hydroxyalkynyl, chloroalkynyl and bromoalkynyl of 3 through 4 carbon atoms and alkoxyalkenyl and alkoxy alkynyl of 3 through 6 carbon atoms; and

R is selected from the group consisting of hydrogen, chlorine, bromine, alkyl, monochloroalkyl, monobromoalkyl, hydroxyalkyl, where each alkyl is 1 through 4 carbon atoms, alkoxy of 1 through 4 carbon atoms,

alkoxyalkyl, alkenyl, chloroalkenyl, bromoalkenyl and alkynyl of 2 through 4 carbon atoms, hydroxyalkenyl,

hydroxyalkynyl, chloroalkynyl and bromoalkynyl of 3 through 4 carbon atoms and alkoxyalkenyl and alkoxyalkynyl of 3 through 6 carbon atoms, with the limitation that R and R cannot both be selected from the group consisting of ethylenic and acetylenic unsaturations at the same time, and with the further limitation that one of m, n and -t must be 1.

2. The method comprising applying to tobacco plants during the period of seven days before to four days after topping a desuckering amount of a compound of the formula:

where X, Y and Z are each selected from the group consisting of chlorine, bromine, fluorine, alkyl of 1 through 4 carbon atoms, and alkoxy of 1 through 4 carbon atoms;

m, it and t are each selected from the group consisting of and 1;

R is selected from the group consisting of vinyl, methylvinyl, chloromethylvinyl, hydroxymethylvinyl, ethynyl, methylethynyl, hydroxymethylethynyl, chlorome-thylethynyl, l-hydroxyalkyl, l-chloroalkyl and l-bromoalkyl where each alkyl group is 1 through 4 carbon atoms and CH Q;

Q is selected from the group consisting of hydrogen, chlorine, bromine, hydroxy, alkyl, monochloroalkyl, monobromoalkyl, hydroxyalkyl where each alkyl is 1 through 4 carbon atoms, alkoxy of 1 through 4 carbon atoms, alkoxyalkyl, alkenyl, chloroalkenyl, bromoalkenyl, and alkynyl of 2 through 4 carbon atoms, hydroxyalkenyl, hydroxyalkynyl, chloroalkynyl and bromoalkynyl of 3 through 4 carbon atoms and alkoxyalkenyl and alkoxyalkynyl of 3 through 6 carbon atoms; and

R is selected from the group consisting of hydrogen, chlorine, bromine, alkyl, monochloroalkyl, monobromoalkyl, hydroxyalkyl, where each alkyl is 1 through 4 carbon atoms, alkoxy of 1 through 4 carbon atoms, alkoxyalkyl, alkenyl, chloroalkenyl, bromoalkenyl and alkynyl of 2 through 4 carbon atoms, hydroxyalkenyl,

hydroxyalkynyl, chloroalkynyl and bromoalkynyl of 3 through 4 carbon atoms and alkoxyalkenyl and alkoxyalkynyl of 3 through 6 carbon atoms, with the limitation that R and R cannot both be selected from the group consisting of ethyleni-c and acetylenic unsaturations at the same time, and with the further limitation that one of m, n and t must be 1.

3. A composition especially useful fior application to tobacco plants comprising 2 to 15% by weight of a compound selected from the group consisting of triethanolamine, di-ethanolamine, di-isopropanolamine and -tri-isopropanolamine, 6 to 35% by weight of dodecyl-benzenesuh fonic acid, 30 to by weight of isophorone and 10 to 30% by weight of a compound selected from the group consisting of m-chlorocarbanilic acid, isopropyl ester; and

m-chlorocarbanilic acid, ester with 1,3-dichloro-2-pro-' panel.

4. Method according to claim 1 wherein the compound applied is m-chlorocarbanilic acid, isopropyl ester.

5. Method according to claim 1 wherein the compound applied is m-chlorocarbanilic acid, ester with 1,3-dichloro- 2-propanol.

6. Method according to claim 1 wherein the compound applied is m-chlorocarbanilic acid, ester with l-methoxy- 2-propanol.

7. Method according to claim 1 wherein the compound applied is m-chlorocarbanilic acid, ester with 2-methyl-3- butyn-Z-ol.

8. Method according to claim 1 wherein the compound applied is 2,5-di-chlorocarbanilic acid, ester with 3-butynol.

9. Method according to claim 1 wherein the compound applied' is o-chlorocarbanilic acid, ester with 2-chloroethanol.

10. Method according to claim 1 wherein the compound applied is m-chlorocarbanilic acid, ester with 3-butyn-2-ol.

11. Method according to claim 1 wherein the compound applied is m-chlorocarbanilic acid, ester with l-chloro-Z- propanol.

References Cited by the Examiner UNITED STATES PATENTS 2,776,196 1/1957 Gysin et al. 7l-2.4 2,776,197 1/1957 Gysin et al. 712.4 2,935,393 5/1960 Luckenbaugh 7l-2'.6

OTHER REFERENCES Hill et al., Chemical Abstracts, vol. 50, 1956, col. 12, 388C.

LEWIS GOTTS, Primary Examiner.

Claims

1. THE METHOD COMPRISING APPLYING A FOLIAR SPRAY TO TOBACCO PLANTS WHILE THE PLANTS ARE IN THE TOPPING STAGE SAID SPRAY COMPRISING A DESUCKERING AMOUNT OF A COMPOUND OF THE FORMULA: