CA1195136A - Method of increasing the recoverable sugar from sugar beets - Google Patents
Method of increasing the recoverable sugar from sugar beetsInfo
- Publication number
- CA1195136A CA1195136A CA000418594A CA418594A CA1195136A CA 1195136 A CA1195136 A CA 1195136A CA 000418594 A CA000418594 A CA 000418594A CA 418594 A CA418594 A CA 418594A CA 1195136 A CA1195136 A CA 1195136A
- Authority
- CA
- Canada
- Prior art keywords
- sugar
- ripener
- methoxy
- hydroxy
- alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
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Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
- A01N37/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
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- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
ABSTRACT OF THE DISCLOSURE
A method :Eor increasing the recoverable suqar Erom suyar beet plants by applying to the sugar beet plants an effective amount of a compound having the structural formula:
A method :Eor increasing the recoverable suqar Erom suyar beet plants by applying to the sugar beet plants an effective amount of a compound having the structural formula:
Description
~.~9a~36 This invention relates to a method of increasiny the yield of sugar ~rom sugar beets~ More particularly, this invention relates to a method of increasing the recovera~le sugar in sugar beets by treating the suyar beet plants during their growth period with benzarnides of 2-methoxy-3,6-dichlorobenzoic acid.
The performance of this process requires the use of an e:Efective amount of the benzamide at least two weeks before haryest. The benzamides of dicamba useful in the present method have the following structural formula:
Ol /R
C N \R]
CH30 ~ ~ Cl Cl wherein R is selected from -the group consisting of hydrogen, alkyl, alkoxy, hydroxy and hydroxyalkyl and Rl is indepen-dently selected from the group consisting of alkyl, alkoxy, hydroxy and hydroxyalkyl.
It is most preferred that the alkyl substituents have a maximum of six carbon atoms.
The above described compounds can be prepared by reacting the corresponding acid chloride with the necessary amine as follows:
0 ,R
C0l Cl ~~~ \ R1 C~-130 ~ ~ R ~ / ~ \
Cl ~ + ~N-E1 - ~ ~ + ~Cl mab~
wherein R and R are as previously defined.
The following examples demonstrate the preparation of the compounds useful in performing the disclosed process.
These benzamide compounds are described in the literature.
~p rati n of N,_-di-methyl- -rnethoY~y-~,6-dichloro-benzamide __~__ Water (150 ml) and potassium carbonate (300 grams) ~ere placed in a 3-liter, 3-necked glass reaction flask equipped with stirrer, thermometer and an ice-water bath. After the exo-therm subsided, ether (70 ml) was added to the mix-ture in small portions with stirring for 10 minutes 2-methoxy-3~6-dichlorobenzoylchlor~de (300 grams, 1.25 mole) was added dropwise with stirring at a rate such that the reaction -temperature did not rise above 7~C~ The reaction mixture was stirred overnight. The salts were filtered off and the filtrate washed with soda ash (20~). The ether was dried over magnesium sulfate, fil-tered and distilled on a steam bath~ The liquid residue was distilled throu~h a Claisen head in vacuo. The desired product was collectea at 107-108~C
0.17mrn ~Ig pressure and was water white.
Preparation of N,N--(2-hydroxyethyl)-2-m thoxy-3,6-dichlorobenzamide Diethanolamine (11 grams; 0.105 mol), triethylamine (12 grams) and toluene (100 ml) were placed in a 25G ml, 3-necked glass reaction flask equipped with stirrer, thermometer and reflux condenser. 2-methoxy-3,6-dichlorobenzoic acid chloride (23.9 grams; 0.1 mol) in toluene (25 ml) were added to the reaction mixture by means of an addition funnel. The reaction rnixture was stirred for 2 hours and then filtered. The recovered solid material was heated in ethyl acetate and filtered. Toluene was added to the oily residue/ heclted to dissolve the oil and cooled. The desired product first formed as an oil and then crystallized. T}-le product
The performance of this process requires the use of an e:Efective amount of the benzamide at least two weeks before haryest. The benzamides of dicamba useful in the present method have the following structural formula:
Ol /R
C N \R]
CH30 ~ ~ Cl Cl wherein R is selected from -the group consisting of hydrogen, alkyl, alkoxy, hydroxy and hydroxyalkyl and Rl is indepen-dently selected from the group consisting of alkyl, alkoxy, hydroxy and hydroxyalkyl.
It is most preferred that the alkyl substituents have a maximum of six carbon atoms.
The above described compounds can be prepared by reacting the corresponding acid chloride with the necessary amine as follows:
0 ,R
C0l Cl ~~~ \ R1 C~-130 ~ ~ R ~ / ~ \
Cl ~ + ~N-E1 - ~ ~ + ~Cl mab~
wherein R and R are as previously defined.
The following examples demonstrate the preparation of the compounds useful in performing the disclosed process.
These benzamide compounds are described in the literature.
~p rati n of N,_-di-methyl- -rnethoY~y-~,6-dichloro-benzamide __~__ Water (150 ml) and potassium carbonate (300 grams) ~ere placed in a 3-liter, 3-necked glass reaction flask equipped with stirrer, thermometer and an ice-water bath. After the exo-therm subsided, ether (70 ml) was added to the mix-ture in small portions with stirring for 10 minutes 2-methoxy-3~6-dichlorobenzoylchlor~de (300 grams, 1.25 mole) was added dropwise with stirring at a rate such that the reaction -temperature did not rise above 7~C~ The reaction mixture was stirred overnight. The salts were filtered off and the filtrate washed with soda ash (20~). The ether was dried over magnesium sulfate, fil-tered and distilled on a steam bath~ The liquid residue was distilled throu~h a Claisen head in vacuo. The desired product was collectea at 107-108~C
0.17mrn ~Ig pressure and was water white.
Preparation of N,N--(2-hydroxyethyl)-2-m thoxy-3,6-dichlorobenzamide Diethanolamine (11 grams; 0.105 mol), triethylamine (12 grams) and toluene (100 ml) were placed in a 25G ml, 3-necked glass reaction flask equipped with stirrer, thermometer and reflux condenser. 2-methoxy-3,6-dichlorobenzoic acid chloride (23.9 grams; 0.1 mol) in toluene (25 ml) were added to the reaction mixture by means of an addition funnel. The reaction rnixture was stirred for 2 hours and then filtered. The recovered solid material was heated in ethyl acetate and filtered. Toluene was added to the oily residue/ heclted to dissolve the oil and cooled. The desired product first formed as an oil and then crystallized. T}-le product
2 -mab/ ~
weighed 23.6 grams representing a yield of 76~.
~ XAMPLE 3 Preparation of N-hydroxy-2-methoxy-3,6-dichloro-benzamide Potassium carbonate (359.7 grams; 2.6 moles) ~/as dissolved in wa-ter (400 ml) in a 5-liter, 3-necked glass reaction flask equipped with stirrer~ thermometer and addition Eunnel.
Ether (2.5 liters) was added to the contents of the flask which were cooled to 0-5C by use of an ice water-salt bath.
Hydroxylamine hydrochloride (181.7 grams; 2.6 moles) was added portionwise to the cooled, stirred solution. The solution was stirred Eor an additional hour after completion of the addition. 2-Methoxy-3,6-dichlorobenzoic acid chloride (479.7 grams; 2.0 moles) was added dropwise from the addition funnel while maintaining the temperature of the mi~ture at 0-5C. The mixture was stirred for an additional two (2) hours after completion of ~he addition. The white solid separated out. It was broken up by vigorous stirriny and filtered. Dilute hydrochloric acid (10%) was prepared from concentrated hydrochloric acid solution ~369 grams) and water (;L030 mls). The solid was added to -the dilute hydro-chloric acid and stirred for two (2) hours. Water was added to the Buchner fil-ter containing the solution and filtered by the use of suction. The filter cake was washed with water and dried under vacuum. The product weighed 433 grams, representing a yield of 92%.
E~PLE 4 Preparation of N--methyl-2-Methoxy-3,6-Dichloro-benzamide Methylamine (146.1 grams~ 4.70 moles) contained in 40% aqueous methyl amine solution (365.4 grams) was ~laced in a 3-liter,
weighed 23.6 grams representing a yield of 76~.
~ XAMPLE 3 Preparation of N-hydroxy-2-methoxy-3,6-dichloro-benzamide Potassium carbonate (359.7 grams; 2.6 moles) ~/as dissolved in wa-ter (400 ml) in a 5-liter, 3-necked glass reaction flask equipped with stirrer~ thermometer and addition Eunnel.
Ether (2.5 liters) was added to the contents of the flask which were cooled to 0-5C by use of an ice water-salt bath.
Hydroxylamine hydrochloride (181.7 grams; 2.6 moles) was added portionwise to the cooled, stirred solution. The solution was stirred Eor an additional hour after completion of the addition. 2-Methoxy-3,6-dichlorobenzoic acid chloride (479.7 grams; 2.0 moles) was added dropwise from the addition funnel while maintaining the temperature of the mi~ture at 0-5C. The mixture was stirred for an additional two (2) hours after completion of ~he addition. The white solid separated out. It was broken up by vigorous stirriny and filtered. Dilute hydrochloric acid (10%) was prepared from concentrated hydrochloric acid solution ~369 grams) and water (;L030 mls). The solid was added to -the dilute hydro-chloric acid and stirred for two (2) hours. Water was added to the Buchner fil-ter containing the solution and filtered by the use of suction. The filter cake was washed with water and dried under vacuum. The product weighed 433 grams, representing a yield of 92%.
E~PLE 4 Preparation of N--methyl-2-Methoxy-3,6-Dichloro-benzamide Methylamine (146.1 grams~ 4.70 moles) contained in 40% aqueous methyl amine solution (365.4 grams) was ~laced in a 3-liter,
3-necked glass reaction flask equip~ed with addition funnel, stirrer~ thermometer and reflu~ condenser and containing ether (1200 ml) cooled to 4C. 2-MethoYy-3,6-dichlorobenzoic acid chloride (375 ~rams; 1.56 moles) in ether (50 ml) ~as added dropwise with stirring maintaining the temperature below 8C
mab/~
After the completion of the addition the reaction rniY~ture was stirred for an additional two (2) hours at a temperature of between 2 and 5C. The insoluble white soli~ was filtered with suction, washed with water, transEerred to 3-liter beaker and stirred fifteen (15) minutes with 10~
sodium carbonate ~2 liters). The insoluble white solid was filtered with suction, washed with water and dried. ~rlhe product weighed 352 grams and had a melting point of 172.5 175~C~
To effect the method of this invention, sugar beet plants are -treated at a comparatively late staye of development with an effective amount of an active compound described above. This treatment is carried out during that stage of development of the sugar beet plant wherein sugar formation takes place. Thus, under normal growing conditions and common cultivation practice the active compounds described can be applied to the sugar beet plants during the period of from about 2 to about 10 weeks before harvesting and preferably during the period of from about four (~) to seven ~7) weeks before harvesting. The use of nitrogen fertilizer, when employed during the cultivation of the sugar beets, is advan~ageously discounted before the applica-tion of the active compounds of this invention.
The amount of the active compound of this invention required to effectively increase the recoverable sugar from sugar beets can vary somewhat dependiny on such factors as the time of applica-tion, the weather, crop density, and the like. Generally an amount of at least about 0.1 ounces per acre and pre~erably an amount of from about 0.5 ounces to about 20 ounces per acre can be used. While amounts greater than those mentioned can be used, -they will not result in an advantage that would warrant their e~pense ancl are therefore not practical.
ma~
For practical use in treating sugar beets, the compounds of this invention are generally incorporated into compositions or formulations which comprise an inert carrier and an effective amount of such a compound. These cornposi-tions enable the active compounds to be conveniently applie~
to the sugar beets i`n any desired quantity. I'hese forMula-tions can be liquids such as solutions, aerosols or emulsifiable concentrates or they can be solids such as dusts, yranules or wettable powders.
The pre~erred compositions are liquid formulations, particularly ernulsifiable cor.centrates. Emulsifiable concen-trates comprise an active compound according to this invention and as the inert carrier, a solventand an emulsifier.
Such emulsifiable concentration of active com?ound ~or application as sprays to -the sugar beets. The emulsifiers most commonly used in these concen-trates are nonionic or mixtures of nonionic with anionic surface-active agents.
Witn -the use of some emulsifi~er systems an inverted emulsion ~water-in-oil) can be prepared.
Solid formulations such as dusts, for example, can be prepared by grinding and blending the active co~pound with a solid inert carrier such as the talcs, clays, silicas, pyrophyllite, and the li~e. Granular formulations can be prepared by impregnating the compound, usually ~issolved in a suitable solvent, onto and into granulated carriers such as the attapulgites or the vermiculites, usually of a parti-cle size range of from about 0.3 to 1~5 mm. ~ettable powders, which can be dispersed in water or oil to any desired concentration oE the active compound, can be prepared by incorporating wetting agents into concentrated dust compositions.
Typical formulations accordin;l to the present inyention useful for increasinq the recoverable sugar in sugar beets are illustrate~d in the fol:lo~in(J e~anlples ;;~ mab/ ~l whereln the quantities are in parts by weight.
Preparation of an Emulsifiable Concentrate _ _ The following ingredients are blended thoroughly until a homogeneous liquid concentrate is obtained. This concentrate is mixed with water to give an aqueous dispersion containing the desired concentration of the active inyredients for use as a spray.
N-methyl-2 methoxy-3,6-dichlorobenzamide 25 Sodium lauryl sulfate2 Sodium lignin sulfate3 Kerosene 70 Preparation of a Wettable Powder The following components are mixed intimately in conventional mixing or blending equipment and are then ground to a powder having an average particle size of less than about 50 microns. The finished powder is dispersed in water to give the desired concentration of active compound.
N,N-dimethyl-2-methoxy-3,6-dichlorbenzamide 50 Fuller's earth 47 Sodium lauryl sulfate2.5 Methyl cellulose 0.5 EX~MPI.E 7 Preparation of a Dust The following ingredients are mixed thoroughly and are -then ground to an average particle size of less than about 50 microns to give a dust suitable for application wi-th conventional dusting equipment.
N-hydroxy-2-methoxy-3,6-dichlorobenzamide 10 Powdered talc 90 Tlle increase in the recoverable sugar from sugar beet plants by the application of the disclosed com-6mab/ ~
3~i pounds was demonstrated by tests perfo.rmed using a standard procedure. Sugar beet plants were sprayed with an approxi-mately diluted emulsifiable concentra-te of the test compourld.
The plants w~re surface i.rriyated at 2-week intervals to maintain normal growth. The crop was harvested and the recoverable sugar deter~ined and measured on a percent basis in comparison -to controls. The results of these tests are reported in Tables 1 - 4. Tables 5, 5A and 5B contain the results of a ~ecord test using the same procedures, but using four di:Eferen-t times- of applying the compound of Example 1.
Product of Exarn~le 1 -RATE OF
APPLICATlON BEET RECOVERY SUGAR RECOVERY
(Ounces/Acre) (Tons/Acre) Percent (Lbs~Acre) Percent of Check of Check 2 20.4 103.0 3~91 101.4 8 21.8 110.1 4081 103 7 26.3 132.8 5176 131.5 Check 19.8 - 3932 Product of Example _ RATE OF
APPLICATION BEET RECOVERY SUGAR RECO'VER'Y
(Ounces/Acre) (I'ons/Acre) Percent (Lbs~Arre~ cc~t of Check of Chec]c 2 ~9.3 102.1 3805.2 103.3 8 21.6 11~.3 ~178.0 113.5 22.2 117.5 ~478.3 121.6 Check 18.9 3681 7 mab/
~53~3~
Product of Example 3 RATE OF
APPLICATION BEET RECOVERY SUGAR RECOVERY
(Ounc ~ Acre) (Tons/Acre) Percent (Lbs/Acre) Percent of Check of Check 1 21.4 106.5 5188106.9 2 18.9 94.0 458894.5
mab/~
After the completion of the addition the reaction rniY~ture was stirred for an additional two (2) hours at a temperature of between 2 and 5C. The insoluble white soli~ was filtered with suction, washed with water, transEerred to 3-liter beaker and stirred fifteen (15) minutes with 10~
sodium carbonate ~2 liters). The insoluble white solid was filtered with suction, washed with water and dried. ~rlhe product weighed 352 grams and had a melting point of 172.5 175~C~
To effect the method of this invention, sugar beet plants are -treated at a comparatively late staye of development with an effective amount of an active compound described above. This treatment is carried out during that stage of development of the sugar beet plant wherein sugar formation takes place. Thus, under normal growing conditions and common cultivation practice the active compounds described can be applied to the sugar beet plants during the period of from about 2 to about 10 weeks before harvesting and preferably during the period of from about four (~) to seven ~7) weeks before harvesting. The use of nitrogen fertilizer, when employed during the cultivation of the sugar beets, is advan~ageously discounted before the applica-tion of the active compounds of this invention.
The amount of the active compound of this invention required to effectively increase the recoverable sugar from sugar beets can vary somewhat dependiny on such factors as the time of applica-tion, the weather, crop density, and the like. Generally an amount of at least about 0.1 ounces per acre and pre~erably an amount of from about 0.5 ounces to about 20 ounces per acre can be used. While amounts greater than those mentioned can be used, -they will not result in an advantage that would warrant their e~pense ancl are therefore not practical.
ma~
For practical use in treating sugar beets, the compounds of this invention are generally incorporated into compositions or formulations which comprise an inert carrier and an effective amount of such a compound. These cornposi-tions enable the active compounds to be conveniently applie~
to the sugar beets i`n any desired quantity. I'hese forMula-tions can be liquids such as solutions, aerosols or emulsifiable concentrates or they can be solids such as dusts, yranules or wettable powders.
The pre~erred compositions are liquid formulations, particularly ernulsifiable cor.centrates. Emulsifiable concen-trates comprise an active compound according to this invention and as the inert carrier, a solventand an emulsifier.
Such emulsifiable concentration of active com?ound ~or application as sprays to -the sugar beets. The emulsifiers most commonly used in these concen-trates are nonionic or mixtures of nonionic with anionic surface-active agents.
Witn -the use of some emulsifi~er systems an inverted emulsion ~water-in-oil) can be prepared.
Solid formulations such as dusts, for example, can be prepared by grinding and blending the active co~pound with a solid inert carrier such as the talcs, clays, silicas, pyrophyllite, and the li~e. Granular formulations can be prepared by impregnating the compound, usually ~issolved in a suitable solvent, onto and into granulated carriers such as the attapulgites or the vermiculites, usually of a parti-cle size range of from about 0.3 to 1~5 mm. ~ettable powders, which can be dispersed in water or oil to any desired concentration oE the active compound, can be prepared by incorporating wetting agents into concentrated dust compositions.
Typical formulations accordin;l to the present inyention useful for increasinq the recoverable sugar in sugar beets are illustrate~d in the fol:lo~in(J e~anlples ;;~ mab/ ~l whereln the quantities are in parts by weight.
Preparation of an Emulsifiable Concentrate _ _ The following ingredients are blended thoroughly until a homogeneous liquid concentrate is obtained. This concentrate is mixed with water to give an aqueous dispersion containing the desired concentration of the active inyredients for use as a spray.
N-methyl-2 methoxy-3,6-dichlorobenzamide 25 Sodium lauryl sulfate2 Sodium lignin sulfate3 Kerosene 70 Preparation of a Wettable Powder The following components are mixed intimately in conventional mixing or blending equipment and are then ground to a powder having an average particle size of less than about 50 microns. The finished powder is dispersed in water to give the desired concentration of active compound.
N,N-dimethyl-2-methoxy-3,6-dichlorbenzamide 50 Fuller's earth 47 Sodium lauryl sulfate2.5 Methyl cellulose 0.5 EX~MPI.E 7 Preparation of a Dust The following ingredients are mixed thoroughly and are -then ground to an average particle size of less than about 50 microns to give a dust suitable for application wi-th conventional dusting equipment.
N-hydroxy-2-methoxy-3,6-dichlorobenzamide 10 Powdered talc 90 Tlle increase in the recoverable sugar from sugar beet plants by the application of the disclosed com-6mab/ ~
3~i pounds was demonstrated by tests perfo.rmed using a standard procedure. Sugar beet plants were sprayed with an approxi-mately diluted emulsifiable concentra-te of the test compourld.
The plants w~re surface i.rriyated at 2-week intervals to maintain normal growth. The crop was harvested and the recoverable sugar deter~ined and measured on a percent basis in comparison -to controls. The results of these tests are reported in Tables 1 - 4. Tables 5, 5A and 5B contain the results of a ~ecord test using the same procedures, but using four di:Eferen-t times- of applying the compound of Example 1.
Product of Exarn~le 1 -RATE OF
APPLICATlON BEET RECOVERY SUGAR RECOVERY
(Ounces/Acre) (Tons/Acre) Percent (Lbs~Acre) Percent of Check of Check 2 20.4 103.0 3~91 101.4 8 21.8 110.1 4081 103 7 26.3 132.8 5176 131.5 Check 19.8 - 3932 Product of Example _ RATE OF
APPLICATION BEET RECOVERY SUGAR RECO'VER'Y
(Ounces/Acre) (I'ons/Acre) Percent (Lbs~Arre~ cc~t of Check of Chec]c 2 ~9.3 102.1 3805.2 103.3 8 21.6 11~.3 ~178.0 113.5 22.2 117.5 ~478.3 121.6 Check 18.9 3681 7 mab/
~53~3~
Product of Example 3 RATE OF
APPLICATION BEET RECOVERY SUGAR RECOVERY
(Ounc ~ Acre) (Tons/Acre) Percent (Lbs/Acre) Percent of Check of Check 1 21.4 106.5 5188106.9 2 18.9 94.0 458894.5
4 . 25.5 126.9 6492133.7 8 17.3 86.1 ~39490.5 16 17.9. 8g.1 47~6g7.8 Check j20.1 - 4855 Product of Example 4 RATE OF
APPLICATION BEET RECOVERY SUGAR RECOVER~Y
~Ounces/Acre) (Tons/Acre) Percent (Lbs7Acre) Percent of Check of Check 2 19.~ 92.0 81.188.3 8 22.8 107.0 99.4108~3 2Q.3 87.595.3 Check 21.3 - 91~8 Product o Example 1 TIME OF APPLICATI~
RATE OF 80~ OF RCW 6 WEEKS BEFORE 3~$ BEFORE
APPLICATION AT PL~NrING CLOSVRE HARVEST ~RVEST
(Ounces/Acre) Pounds Of Pounds of Pounds of Pounds of Beets Beets BeetsBeets 4 185.4 182.8 183.577 8 8 170.2 168.3 174.1170.8 16 168.0 167.4 183.3172.5 32 171.8 178.9 166.9166.~
~hec]c 166.8 179.6 162.3167.5 ` - 8 mab/~
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APPLICATION BEET RECOVERY SUGAR RECOVER~Y
~Ounces/Acre) (Tons/Acre) Percent (Lbs7Acre) Percent of Check of Check 2 19.~ 92.0 81.188.3 8 22.8 107.0 99.4108~3 2Q.3 87.595.3 Check 21.3 - 91~8 Product o Example 1 TIME OF APPLICATI~
RATE OF 80~ OF RCW 6 WEEKS BEFORE 3~$ BEFORE
APPLICATION AT PL~NrING CLOSVRE HARVEST ~RVEST
(Ounces/Acre) Pounds Of Pounds of Pounds of Pounds of Beets Beets BeetsBeets 4 185.4 182.8 183.577 8 8 170.2 168.3 174.1170.8 16 168.0 167.4 183.3172.5 32 171.8 178.9 166.9166.~
~hec]c 166.8 179.6 162.3167.5 ` - 8 mab/~
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Claims (7)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. A method for increasing the recoverable sugar from sugar beets, comprising: contacting sugar beet plants during the period of from about 2 to about 10 weeks before harvest with an effective amount of a sugar ripener having the following structural formula:
wherein R is selected from the group consisting of hydrogen, hydroxy, alkyl, alkoxy and hydroxyalkyl, and R1 is, independently, selected from the group consisting of hydroxy, alkyl, alkoxy and hydroxyalkyl, wherein each alkyl group has a maximum of 6 carbon atoms
wherein R is selected from the group consisting of hydrogen, hydroxy, alkyl, alkoxy and hydroxyalkyl, and R1 is, independently, selected from the group consisting of hydroxy, alkyl, alkoxy and hydroxyalkyl, wherein each alkyl group has a maximum of 6 carbon atoms
2. The method of claim 1, wherein the sugar beet plants are contacted with at least 0.5 ounces per acre of the sugar ripener.
3. The method of claim 1 or 2, wherein the sugar ripener is N,N-dimethyl-2-methoxy-3,6-dichlorobenzamide.
A. The method of claim 1 or 2, wherein the sugar ripener is N,N-(2'-hydroxyethyl)-2-methoxy-3,6-dichlorobenzamide.
5. The method of claim 1 or 2, wherein the sugar ripener is N-hydroxy-2-methoxy-3,6-dichlorobenzamide.
6. The method of claim 1 or 2, wherein the sugar ripener is N-methyl-2-methoxy-3,6-dichlorobenzamide.
7. The method of claim 1 or 2, wherein the sugar ripener is contacted with the sugar beet plants from about 4 to about 7 weeks before harvest.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34668782A | 1982-02-08 | 1982-02-08 | |
| US346,687 | 1989-05-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1195136A true CA1195136A (en) | 1985-10-15 |
Family
ID=23360583
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000418594A Expired CA1195136A (en) | 1982-02-08 | 1982-12-24 | Method of increasing the recoverable sugar from sugar beets |
Country Status (6)
| Country | Link |
|---|---|
| CA (1) | CA1195136A (en) |
| CS (1) | CS241135B2 (en) |
| DD (1) | DD207142A5 (en) |
| DE (1) | DE3303678A1 (en) |
| FR (1) | FR2521130B1 (en) |
| GB (1) | GB2117750B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8829204D0 (en) * | 1988-12-14 | 1989-01-25 | Sandoz Ltd | Improvements in or relating to organic compounds |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1351438A (en) * | 1961-11-03 | 1964-02-07 | Velsicol Chemical Corp | Herbicidal compositions |
| GB1028976A (en) * | 1962-02-23 | 1966-05-11 | Fisons Pest Control Ltd | Plant treatment process |
| GB1021893A (en) * | 1962-02-23 | 1966-03-09 | Fisons Pest Control Ltd | Plant treatment process |
| US3474167A (en) * | 1965-06-04 | 1969-10-21 | Nippon Soda Co | Substituted benzohydroxamates and their use as acaricides |
| US3767377A (en) * | 1970-11-02 | 1973-10-23 | Velsicol Chemical Corp | Method of increasing the recoverable sugar from sugar cane |
| GB1329201A (en) * | 1971-01-15 | 1973-09-05 | Velsicol Chemical Corp | Method of increasing recoverable sugar from sugar beets |
-
1982
- 1982-12-24 CA CA000418594A patent/CA1195136A/en not_active Expired
-
1983
- 1983-01-14 CS CS83269A patent/CS241135B2/en unknown
- 1983-01-24 FR FR8301019A patent/FR2521130B1/en not_active Expired
- 1983-02-03 DE DE19833303678 patent/DE3303678A1/en not_active Withdrawn
- 1983-02-07 DD DD24774683A patent/DD207142A5/en not_active IP Right Cessation
- 1983-02-08 GB GB08303364A patent/GB2117750B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DD207142A5 (en) | 1984-02-22 |
| GB8303364D0 (en) | 1983-03-16 |
| FR2521130B1 (en) | 1988-07-15 |
| GB2117750A (en) | 1983-10-19 |
| FR2521130A1 (en) | 1983-08-12 |
| DE3303678A1 (en) | 1983-08-18 |
| CS26983A2 (en) | 1985-06-13 |
| GB2117750B (en) | 1985-07-03 |
| CS241135B2 (en) | 1986-03-13 |
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| MKEC | Expiry (correction) | ||
| MKEX | Expiry |