CA1060012A - N-carbamoyl ethyl oxanilates - Google Patents
N-carbamoyl ethyl oxanilatesInfo
- Publication number
- CA1060012A CA1060012A CA247,999A CA247999A CA1060012A CA 1060012 A CA1060012 A CA 1060012A CA 247999 A CA247999 A CA 247999A CA 1060012 A CA1060012 A CA 1060012A
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- Prior art keywords
- chloro
- methyl
- compound according
- group
- compound
- 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.)
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/64—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups singly-bound to oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/16—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with acylated ring nitrogen atom
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
Abstract of the Disclosure A composition of matter is described herein which has herbicidal activity and methods of use.
The composition is defined by the following generic formula wherein X and Y are independently selected from the group consisting of chloro, bromo, and trifluoromethyl; n is either 0 or 1; m is either 0 or 1; and R and R1 are independently selected from the group consisting of lower alkyl from C1 to C3, inclusive, and lower alkoxy from C1 to C3, inclusive, or R and R1 taken together is selected from the group con-sisting of , , and
The composition is defined by the following generic formula wherein X and Y are independently selected from the group consisting of chloro, bromo, and trifluoromethyl; n is either 0 or 1; m is either 0 or 1; and R and R1 are independently selected from the group consisting of lower alkyl from C1 to C3, inclusive, and lower alkoxy from C1 to C3, inclusive, or R and R1 taken together is selected from the group con-sisting of , , and
Description
~6S)01Z
Brief Description and Background of the Invention This invention relates to a class of substituted ethyl oxani-lates and to their use as herbicides. More specifically this invention relates to N-(carbamoyl) ethyl oxanilates, which are represented by the formula Xn ~
Ym~-C-C-OC 2H5 1 0 IC=O
; / N
R
wherein X and Y are independently selected from the group con- ~7 sisting of chloro, bromo and trifluoromethyl; n is either 0 or 1;
m is either 0 or 1; and R and Rl are independently selected from -the group consisting of lower alkyl from Cl to C3, inclusive, and :
1 lower alkoxy from Cl to C3, inclusive, or R and Rl taken together 7 is selected from the group consisting of ~ -:~ :
~ 20 ~ I ~ CH3 , and ~ O . ~ :
. 9 :7 Because of the N-(carbamoyl) substitution, the generic i structure of the compound of this invention is similar to that of a tetra-substituted urea. An example of such a urea teaching a monocarbonyl radical bonded to a nitrogen atom which is also ~ `
¦ bonded to a halogenated phenyl radical is described in French :3: Patent No. 1,250,422. The compound of the present invention differs from that described in the above-mentioned patent in that it teaches the preparation and herbicidal use of a variety of oxanilates which, because of their characteristic adjacent pair of carbonyl groups, are beyond the scope of the above-mentioned patent.
, ~ ': ", . ' ';"' "' . i , . .. .
1.06~012 Detailed Description of the Invention In the practice of the present invention, the novel com-pounds of the present invention are manufactured by reacting the properly selected 1,3,3-trisubstituted urea with sodium hydride and then reacting the resulting sodium salt of the urea with ethyl-oxalyl chloride to obtain the N-(carbamoyl) ethyl oxanilate, as shown in the examples herein. Following the examples of prepara-tion is a table of compounds which are prepared according to the procedures described herein. Compound numbers have been assigned to them and are used for identification throughout the balance of the specification. These compounds are used as herbicides and can be applied by methods and means as hereinafter disclosed.
N-(dimethylcarbamoyl) ethyl-3'-trifluoromethyl oxanilate.
;Sodium hydride (21.6 g., .9 mole) was suspended in 300 ml.
- of tetrahydrofuran (dried over molecular sieve) and a solution of ~l-(m-trifluoromethylphenyl)-3,3-dimethyl urea (191 g., .823 mole) :,.j . . : .
~in 1700 ml. dry tetrahydrofuran was added dropwise under argon at .. i room temperature. The mixture was stirred one hour at room ,20 temperature and one hour at 40-45C. The solution was decanted under argon and added dropwise to a solution of ethyloxalyl chloride 120 g., (.88 mole) in 200 ml. of tetrahydrofuran. During the addition, the reactor was cooled with water to maintain the reactor temperature at 43C or below. A precipitate appeared and the mixture was stirred approximately 16 hours at room tempera-ture, then stirred for 1 hour at 45C. The volatiles were re-~,moved from the reaction mixture ln vacuo. The residue was dis-solved in 600 ml. of benzene and 200 ml. of 5% sodlum bicarbonate solution. The organic layer was washed with 200 ml. additional bicarbonate solution and dried over magnesium sulfate. The sol-vent was removed ln vacuo and the remaining crude product was '; : ' ~ 3 ~ -,, .
:- ; ' 106VOlZ
recrystallized from a benzene-hexane mixture. The yield of the product was 175.7 g. or 65% of theory. The melting point was 67-69C. The structure of the product was confirmed by infrared and NMR spectra.
N-(dimethylcarbamoyl)-ethyl-3',4'-dichlorooxanilate.
; Sodium hydride (24.5 g., 1.02 moles) was suspended in 300 ml.
; of dry tetrahydrofuran. 217 g. (.93 mole) of 1-(3,4-dichloro-phenyl)-3,3-dimethyl urea in 1600 ml. of tetrahydrofuran was added dropwise to the sodium hydride under argon at room temperature.
The mixture was then stirred for 1 hour at room temperature and for another hour at 40-45C. The solution was transferred under ` argon to an additional funnel and added dropwise to 136.5 g. (1.0 mole) of ethyloxalyl chloride which was dissolved in 180 ml.
tetrahydrofuran. The temperature was allowed to rise at 43C. -i The mixture was then stirred for 2 hours at room temperature, followed by 1.5 hours at 40-45C., and finally approximately 16 ~-hours at room temperature. The volatiles were removed in vacuo and the residue was treated with 800 ml. of benzene and 400 ml.
; 20 of 5% sodium bicarbonate solution. The insoluble material was filtered, washed with benzene, and dried. The original benzene filtrate was washed with two further 200 ml~ portions of 5% sodium bicarbonate solution and dried over magnesium sulfate. This solu-tion was concentrated in vacuo, filtered, and the filter cake , .
/l washed with hexane and dried. This was combined with the original ~ . .
filter cake to give 249.8 g. (80% of theoretical yield) of product with a melting point of 123-124C. The structure of the ' ~ product was confirmed by infrared and NMR spectra.
,s .. : -:
~ 30 ,' ~' ' ', :
" 1060012 TABLE I
Xn y ~ 1l 1l m ~-C-C-OC2H5 Cl=O :
R / \ R
COMPOUND
NUMBER n X m Y R Rl 1 0 - l 4-Cl CH3 3 , .
Brief Description and Background of the Invention This invention relates to a class of substituted ethyl oxani-lates and to their use as herbicides. More specifically this invention relates to N-(carbamoyl) ethyl oxanilates, which are represented by the formula Xn ~
Ym~-C-C-OC 2H5 1 0 IC=O
; / N
R
wherein X and Y are independently selected from the group con- ~7 sisting of chloro, bromo and trifluoromethyl; n is either 0 or 1;
m is either 0 or 1; and R and Rl are independently selected from -the group consisting of lower alkyl from Cl to C3, inclusive, and :
1 lower alkoxy from Cl to C3, inclusive, or R and Rl taken together 7 is selected from the group consisting of ~ -:~ :
~ 20 ~ I ~ CH3 , and ~ O . ~ :
. 9 :7 Because of the N-(carbamoyl) substitution, the generic i structure of the compound of this invention is similar to that of a tetra-substituted urea. An example of such a urea teaching a monocarbonyl radical bonded to a nitrogen atom which is also ~ `
¦ bonded to a halogenated phenyl radical is described in French :3: Patent No. 1,250,422. The compound of the present invention differs from that described in the above-mentioned patent in that it teaches the preparation and herbicidal use of a variety of oxanilates which, because of their characteristic adjacent pair of carbonyl groups, are beyond the scope of the above-mentioned patent.
, ~ ': ", . ' ';"' "' . i , . .. .
1.06~012 Detailed Description of the Invention In the practice of the present invention, the novel com-pounds of the present invention are manufactured by reacting the properly selected 1,3,3-trisubstituted urea with sodium hydride and then reacting the resulting sodium salt of the urea with ethyl-oxalyl chloride to obtain the N-(carbamoyl) ethyl oxanilate, as shown in the examples herein. Following the examples of prepara-tion is a table of compounds which are prepared according to the procedures described herein. Compound numbers have been assigned to them and are used for identification throughout the balance of the specification. These compounds are used as herbicides and can be applied by methods and means as hereinafter disclosed.
N-(dimethylcarbamoyl) ethyl-3'-trifluoromethyl oxanilate.
;Sodium hydride (21.6 g., .9 mole) was suspended in 300 ml.
- of tetrahydrofuran (dried over molecular sieve) and a solution of ~l-(m-trifluoromethylphenyl)-3,3-dimethyl urea (191 g., .823 mole) :,.j . . : .
~in 1700 ml. dry tetrahydrofuran was added dropwise under argon at .. i room temperature. The mixture was stirred one hour at room ,20 temperature and one hour at 40-45C. The solution was decanted under argon and added dropwise to a solution of ethyloxalyl chloride 120 g., (.88 mole) in 200 ml. of tetrahydrofuran. During the addition, the reactor was cooled with water to maintain the reactor temperature at 43C or below. A precipitate appeared and the mixture was stirred approximately 16 hours at room tempera-ture, then stirred for 1 hour at 45C. The volatiles were re-~,moved from the reaction mixture ln vacuo. The residue was dis-solved in 600 ml. of benzene and 200 ml. of 5% sodlum bicarbonate solution. The organic layer was washed with 200 ml. additional bicarbonate solution and dried over magnesium sulfate. The sol-vent was removed ln vacuo and the remaining crude product was '; : ' ~ 3 ~ -,, .
:- ; ' 106VOlZ
recrystallized from a benzene-hexane mixture. The yield of the product was 175.7 g. or 65% of theory. The melting point was 67-69C. The structure of the product was confirmed by infrared and NMR spectra.
N-(dimethylcarbamoyl)-ethyl-3',4'-dichlorooxanilate.
; Sodium hydride (24.5 g., 1.02 moles) was suspended in 300 ml.
; of dry tetrahydrofuran. 217 g. (.93 mole) of 1-(3,4-dichloro-phenyl)-3,3-dimethyl urea in 1600 ml. of tetrahydrofuran was added dropwise to the sodium hydride under argon at room temperature.
The mixture was then stirred for 1 hour at room temperature and for another hour at 40-45C. The solution was transferred under ` argon to an additional funnel and added dropwise to 136.5 g. (1.0 mole) of ethyloxalyl chloride which was dissolved in 180 ml.
tetrahydrofuran. The temperature was allowed to rise at 43C. -i The mixture was then stirred for 2 hours at room temperature, followed by 1.5 hours at 40-45C., and finally approximately 16 ~-hours at room temperature. The volatiles were removed in vacuo and the residue was treated with 800 ml. of benzene and 400 ml.
; 20 of 5% sodium bicarbonate solution. The insoluble material was filtered, washed with benzene, and dried. The original benzene filtrate was washed with two further 200 ml~ portions of 5% sodium bicarbonate solution and dried over magnesium sulfate. This solu-tion was concentrated in vacuo, filtered, and the filter cake , .
/l washed with hexane and dried. This was combined with the original ~ . .
filter cake to give 249.8 g. (80% of theoretical yield) of product with a melting point of 123-124C. The structure of the ' ~ product was confirmed by infrared and NMR spectra.
,s .. : -:
~ 30 ,' ~' ' ', :
" 1060012 TABLE I
Xn y ~ 1l 1l m ~-C-C-OC2H5 Cl=O :
R / \ R
COMPOUND
NUMBER n X m Y R Rl 1 0 - l 4-Cl CH3 3 , .
2 1 3-Cl l 4-Cl CH3 C 3
3 0 - l 3-CF3 CH3 ' 4 1 3-Cl l 5-Cl ,~ .
5 l 3-Cl l 4-Cl OCH3 CH3 6 l 3-Cl l 4-Br OCH3 3 ~i 7 l 3-Cl 1 4-C1 3 8 1 3-Cl 1 4-Cl '~
HERBICIDAL SCREENING TESTS
As previously mentioned, the herein described compounds produced in the above-described manner are phytotoxic compounds which are useful and valuable in controlling various plant species.
Compounds of this invention are tested as herbicides in the fol-:~ ~
~1 lowing manner.
;~ Pre-emergence Herbic de Screening Test Using an analytical balance, 20 mg. of the compound to be tested is weighed out on a piece of glassine weighing paper. The 1~1 paper and compound are placed in a 30 ml. wide-mouth bottle and 3 ml. of acetone containing 1% Tween 20 ~ (polyoxyethylene sorbitan monolaurate) is added to dissolve the compound. If the material ~ ~ .
~ - 5 -"~
': 1 ,, .
., ,.. ... . . , . , . . . ~ . . .. : : . : . . .
106~0~Z
is not soluble in acetone, another solvent such as water, alcohol or dimethylformamide (DMF) is used instead. When DMF is used, only 0.5 ml. or less is used to dissolve the compound and then another solvent is used to make the volume up to 3 ml. The 3 ml.
solution is sprayed uniformly on the soil contained in a small flat one day after planting weed seeds in the flat of soil. An atomizer is used to apply the spray using compressed air at a pressure of 5 lb/sq. inch. The rate of application is 8 lb/acre and the spray volume is 143 gallons per acre.
On the day preceding treatment, the flat which is 7 inches long, 5 inches wide and 2.75 inches deep, is filled to a depth of 2 inches with loamy sand soil. Seeds of seven different weed species are planted in individual rows using one species per row across the width of the flat. The seeds are covered with soil so that they are planted at a depth of 0.5 inch. Ample seeds are planted to give about 20 to 50 seedlings per row after emergence depending on the size of the plants.
The seeds used are foxtail (Setaria spp.), watergrass (Echinochloa crusgalli), red oat (Avena sativa), redroot pigweed ., .-~ 20 (Amaranthus retroflexus), mustard (Brassica juncea), curly dock , (Rumex crispus), and hairy crabgrass (Digitaria sanguinalis).
After treatment, the flats are placed in the greenhouse at -- 1 , . .
~ a temperature of 70 to 85F and watered by sprinkling. Two weeks .. ~ ~ -.. . .
after treatment, the degree of injury or control is determined by comparison with untreated check plants of the same age. The injury rating from 0 to 100% is recorded for each species as per ~~ cent control with 0% representing no injury and 100% representing -i complete kill. ~--~ Post-emergence Herbicide Screening Test ~-Seeds of six plant species, including hairy crabgrass, water-grass, red oat, mustard, curly dock and Pinto beans (Phaseolus .. .. ..
vulqaris), are planted in the flats as described above for pre-,' emergence screening. The flats are placed in the greenhouse at 70 to 850F and watered daily with a sprinkler. About 10 to 14 days after planting when the primary leaves of the bean plants are almost fully expanded and the first trifoliate leaves are just starting to form, the plants are sprayed. The spray is prepared by weighing out 20 mg. of the test compound, dissolving it in 5 ml. of acetone containing 1~ Tween 20 ~ (polyoxyethylene sorbi-tan monolaurate) and then adding 5 ml. of water. The solution is sprayed on the foliage using an atomizer at an air pressure of 5 lb/sq. inch. The spray concentration is 0.2~ and the rate is 8 lb/acre. The spray volume is 476 gallons per acre.
The results of these tests are shown in Table II.
TABLE II
HERBICIDAL ACTIVITY - SCREENING RESULTS
Compound Pre-emergence Post-emergence Number (Average of 7 plant species) (Average of 6 plant species) ., .
3 99.6 100 100 99 ~
!
8 55 96 -~
The compounds of the present invention are used as pre-emergence or post-emergence herbicides and are applied in a variety of ways at various concentrations. In practice, the com-` pounds are formulated with an inert carrier, utilizing methods .
well known to those skilled in the art, thereby maklng them suit-able for application as dusts, sprays, or drenches and the like, in the form and manner required. The mixtures can be dispersed ., .
, , ~ , . ~ , -.. . . ~ :
in water with the aid of a wetting agent or they can be employed in organic liquid compositions, oil and water, water in oil emulsions, with or without the addition of wetting, dispersing or emulsifying agents. An herbicidally effective amount depends upon the nature of the seeds or plants to be controlled and the rate of application varies from 0.10 to approximately 50 pounds per acre.
The concentration of a compound of the present invention, consti-tuting an effective amount in the best mode of administration in the utility disclosed, is readily determinable by those skilled in the art.
The phytotoxic compositions of this invention employing an herbicidally effective amount of the compound described herein are applied to the plants in the conventional manner. Thus, the dusts and liquid compositions can be applied to the plant by the use of power dusters, boom and hand sprayers and spray dusters.
The compositions can also be applied from airplanes as a dust or ,~, . . ':
a spray because they are effective in very low dosages. In order to modify or control growth of germinating seeds or emerging -~
seedlings, as a typical example, the dust and liquid compositions are applied to the soil according to conventional methods and are distributed in the soil to a depth of at least one-half inch ~-below the soil surface. It is not necessary that the phytotoxic compositions be admixed with the soil particles and these compo-' sitions can be applied merely by spraying or sprinkling the sur-j face of the soil. The phytotoxic compositions of this invention can also be applied by addition to irrigation water supplied to the field to be treated. This method of application permits the penetration of the compositions into the soil as the water is absorbed therein. Dust compositions, granular compositions or liquid formulations applied to the surface of the soil can be distributed below the surface of the soil by conventional means such as discing, dragging or mixing operations.
.
:, .
The phytotoxic compositions of this invention can also con-tain other additaments, for example, fertilizers, pesticides and the like, used as adjuvant or in combination with any of the above-described adjuvants. Other phytotoxic compounds useful in combina-tion with the above-described compounds include, for example, 2,4-dichlorophenoxyacetic acids, 2,4,5-trichlorophenoxyacetic acid, 2-methyl-4-chlorophenoxyacetic acid and the salts, esters and amides thereof; triazine derivatives, such as 2,4-bis(3-methoxy-propylamino)-6-methyl-thio-s-triazine; 2-chloro-4-ethylamino-6-isopropylamino-s-triazine, and 2-ethylamino-4-isopropylamino-6-methylmercapto-s-triazine, urea derivatives, such as 3-(3,4-di-chlorophenyl)-l,l-dimethyl urea and acetamides such as N,N-di-allyli~-chloroacetamlde, N-(~-chloroacetyl) hexamethyleneimine, and N,N-diethyl-~-bromoacetamide, and the like; benzoic acids such as 3-amino-2,5-dichlorobenzoic; S-ethyl-dipropylthiocarbamate; S-ethyl hexahydro-lH-azepine-l-carbothioate and the like. Fertili-~- zers useful in combination with the active ingredients include, for example, ammonium nitrate, urea and superphosphate. Other useful additaments include materials in which plant organisms take root and grow, such as compost, manure, humus, sand and the like.
Various changes and modifications are possible without departing from the spirit and scope of the invention described herein and will be apparent to those skilled in the art to which it pertains. It is accordingly intended that the present inven-tion shall be limited only by the scope of the claims.
., .
' ' ., :
_ g _ . , .
. . . - : . . .
5 l 3-Cl l 4-Cl OCH3 CH3 6 l 3-Cl l 4-Br OCH3 3 ~i 7 l 3-Cl 1 4-C1 3 8 1 3-Cl 1 4-Cl '~
HERBICIDAL SCREENING TESTS
As previously mentioned, the herein described compounds produced in the above-described manner are phytotoxic compounds which are useful and valuable in controlling various plant species.
Compounds of this invention are tested as herbicides in the fol-:~ ~
~1 lowing manner.
;~ Pre-emergence Herbic de Screening Test Using an analytical balance, 20 mg. of the compound to be tested is weighed out on a piece of glassine weighing paper. The 1~1 paper and compound are placed in a 30 ml. wide-mouth bottle and 3 ml. of acetone containing 1% Tween 20 ~ (polyoxyethylene sorbitan monolaurate) is added to dissolve the compound. If the material ~ ~ .
~ - 5 -"~
': 1 ,, .
., ,.. ... . . , . , . . . ~ . . .. : : . : . . .
106~0~Z
is not soluble in acetone, another solvent such as water, alcohol or dimethylformamide (DMF) is used instead. When DMF is used, only 0.5 ml. or less is used to dissolve the compound and then another solvent is used to make the volume up to 3 ml. The 3 ml.
solution is sprayed uniformly on the soil contained in a small flat one day after planting weed seeds in the flat of soil. An atomizer is used to apply the spray using compressed air at a pressure of 5 lb/sq. inch. The rate of application is 8 lb/acre and the spray volume is 143 gallons per acre.
On the day preceding treatment, the flat which is 7 inches long, 5 inches wide and 2.75 inches deep, is filled to a depth of 2 inches with loamy sand soil. Seeds of seven different weed species are planted in individual rows using one species per row across the width of the flat. The seeds are covered with soil so that they are planted at a depth of 0.5 inch. Ample seeds are planted to give about 20 to 50 seedlings per row after emergence depending on the size of the plants.
The seeds used are foxtail (Setaria spp.), watergrass (Echinochloa crusgalli), red oat (Avena sativa), redroot pigweed ., .-~ 20 (Amaranthus retroflexus), mustard (Brassica juncea), curly dock , (Rumex crispus), and hairy crabgrass (Digitaria sanguinalis).
After treatment, the flats are placed in the greenhouse at -- 1 , . .
~ a temperature of 70 to 85F and watered by sprinkling. Two weeks .. ~ ~ -.. . .
after treatment, the degree of injury or control is determined by comparison with untreated check plants of the same age. The injury rating from 0 to 100% is recorded for each species as per ~~ cent control with 0% representing no injury and 100% representing -i complete kill. ~--~ Post-emergence Herbicide Screening Test ~-Seeds of six plant species, including hairy crabgrass, water-grass, red oat, mustard, curly dock and Pinto beans (Phaseolus .. .. ..
vulqaris), are planted in the flats as described above for pre-,' emergence screening. The flats are placed in the greenhouse at 70 to 850F and watered daily with a sprinkler. About 10 to 14 days after planting when the primary leaves of the bean plants are almost fully expanded and the first trifoliate leaves are just starting to form, the plants are sprayed. The spray is prepared by weighing out 20 mg. of the test compound, dissolving it in 5 ml. of acetone containing 1~ Tween 20 ~ (polyoxyethylene sorbi-tan monolaurate) and then adding 5 ml. of water. The solution is sprayed on the foliage using an atomizer at an air pressure of 5 lb/sq. inch. The spray concentration is 0.2~ and the rate is 8 lb/acre. The spray volume is 476 gallons per acre.
The results of these tests are shown in Table II.
TABLE II
HERBICIDAL ACTIVITY - SCREENING RESULTS
Compound Pre-emergence Post-emergence Number (Average of 7 plant species) (Average of 6 plant species) ., .
3 99.6 100 100 99 ~
!
8 55 96 -~
The compounds of the present invention are used as pre-emergence or post-emergence herbicides and are applied in a variety of ways at various concentrations. In practice, the com-` pounds are formulated with an inert carrier, utilizing methods .
well known to those skilled in the art, thereby maklng them suit-able for application as dusts, sprays, or drenches and the like, in the form and manner required. The mixtures can be dispersed ., .
, , ~ , . ~ , -.. . . ~ :
in water with the aid of a wetting agent or they can be employed in organic liquid compositions, oil and water, water in oil emulsions, with or without the addition of wetting, dispersing or emulsifying agents. An herbicidally effective amount depends upon the nature of the seeds or plants to be controlled and the rate of application varies from 0.10 to approximately 50 pounds per acre.
The concentration of a compound of the present invention, consti-tuting an effective amount in the best mode of administration in the utility disclosed, is readily determinable by those skilled in the art.
The phytotoxic compositions of this invention employing an herbicidally effective amount of the compound described herein are applied to the plants in the conventional manner. Thus, the dusts and liquid compositions can be applied to the plant by the use of power dusters, boom and hand sprayers and spray dusters.
The compositions can also be applied from airplanes as a dust or ,~, . . ':
a spray because they are effective in very low dosages. In order to modify or control growth of germinating seeds or emerging -~
seedlings, as a typical example, the dust and liquid compositions are applied to the soil according to conventional methods and are distributed in the soil to a depth of at least one-half inch ~-below the soil surface. It is not necessary that the phytotoxic compositions be admixed with the soil particles and these compo-' sitions can be applied merely by spraying or sprinkling the sur-j face of the soil. The phytotoxic compositions of this invention can also be applied by addition to irrigation water supplied to the field to be treated. This method of application permits the penetration of the compositions into the soil as the water is absorbed therein. Dust compositions, granular compositions or liquid formulations applied to the surface of the soil can be distributed below the surface of the soil by conventional means such as discing, dragging or mixing operations.
.
:, .
The phytotoxic compositions of this invention can also con-tain other additaments, for example, fertilizers, pesticides and the like, used as adjuvant or in combination with any of the above-described adjuvants. Other phytotoxic compounds useful in combina-tion with the above-described compounds include, for example, 2,4-dichlorophenoxyacetic acids, 2,4,5-trichlorophenoxyacetic acid, 2-methyl-4-chlorophenoxyacetic acid and the salts, esters and amides thereof; triazine derivatives, such as 2,4-bis(3-methoxy-propylamino)-6-methyl-thio-s-triazine; 2-chloro-4-ethylamino-6-isopropylamino-s-triazine, and 2-ethylamino-4-isopropylamino-6-methylmercapto-s-triazine, urea derivatives, such as 3-(3,4-di-chlorophenyl)-l,l-dimethyl urea and acetamides such as N,N-di-allyli~-chloroacetamlde, N-(~-chloroacetyl) hexamethyleneimine, and N,N-diethyl-~-bromoacetamide, and the like; benzoic acids such as 3-amino-2,5-dichlorobenzoic; S-ethyl-dipropylthiocarbamate; S-ethyl hexahydro-lH-azepine-l-carbothioate and the like. Fertili-~- zers useful in combination with the active ingredients include, for example, ammonium nitrate, urea and superphosphate. Other useful additaments include materials in which plant organisms take root and grow, such as compost, manure, humus, sand and the like.
Various changes and modifications are possible without departing from the spirit and scope of the invention described herein and will be apparent to those skilled in the art to which it pertains. It is accordingly intended that the present inven-tion shall be limited only by the scope of the claims.
., .
' ' ., :
_ g _ . , .
. . . - : . . .
Claims (32)
1. The compound having the formula wherein X and Y are independently selected from the group consis-ting of chloro, bromo and trifluoromethyl; n is either 0 or 1; m is either 0 or 1; R and R1 are independently selected from the group consisting of lower alkyl from C1 to C3, inclusive, and lower alkoxy from C1 to C3, inclusive; R and R1 taken together is selected from the group consisting of , and .
2. A compound according to Claim 1 in which Y is chloro, n is 0, m is 1, and R and R1 are independently lower alkyl.
3. A compound according to Claim 2 in which Y is 4-chloro, and R and R1 are each methyl.
4. A compound according to Claim 1 in which Y is trifluoro-methyl, n is 0, m is 1, and R and R1 are independently lower alkyl.
5. A compound according to Claim 4 in which Y is 3-trifluoro-methyl and R and R1 are each methyl.
6. A compound according to Claim 1 in which X is chloro, Y is chloro, n is 1, m is 1, and R and R1 are independently lower alkyl.
7. A compound according to Claim 6 in which X is 3-chloro, Y is 4-chloro, and R and R1 are each methyl.
8. A compound according to Claim 1 in which X and Y are independently selected from the group consisting of chloro and bromo, n is 1, m is 1, R is alkyl and R1 is alkoxy.
9. A compound according to Claim 8 in which X is 3-chloro, Y is 4-bromo, R is methyl and R1 is methoxy.
10. A compound according to Claim 8 in which X is 3-chloro, Y is 4-chloro, R is methyl and R1 is methoxy.
11. A compound according to Claim 1 in which R and R1 taken together is , X is chloro, Y is chloro, n is 1, and m is 1.
12. A compound according to Claim 11 in which X is 3-chloro, and Y is 5-chloro.
13. A compound according to Claim 1 in which R and R1 taken together is , X is chloro, Y is chloro, n is 1, and m is 1.
14. A compound according to Claim 13 in which X is 3-chloro and Y is 4-chloro.
15. A compound according to Claim 1 in which R and R1 taken together is , X is chloro, Y is chloro, n is 1, and m is 1.
16. A compound according to Claim 15 in which X is 3-chloro and Y is 4-chloro.
17. The method of controlling undesirable vegetation com-prising applying to the locus where control is desired a phyto-toxic amount of a compound having the formula wherein X and Y are independently selected from the group con-sisting of chloro, bromo and trifluoromethyl; n is either 0 or 1;
m is either 0 or 1; R and R1 are independently selected from the group consisting of lower alkyl from C1 to C3, inclusive, and lower alkoxy from C1 to C3, inclusive; R and R1 taken together is selected from the group consisting of , and .
m is either 0 or 1; R and R1 are independently selected from the group consisting of lower alkyl from C1 to C3, inclusive, and lower alkoxy from C1 to C3, inclusive; R and R1 taken together is selected from the group consisting of , and .
18. A method according to Claim 17 in which Y is chloro, n is 0, m is 1, and R and R1 are independently lower alkyl.
19. A method according to Claim 18 in which Y is 4-chloro and R and R1 are each methyl.
20. A method according to Claim 17 in which Y is trifluoro-methyl, n is 0, m is 1, and R and R1 are independently lower alkyl.
21. A method according to Claim 20 in which Y is 3-tri-fluoromethyl and R and R1 are each methyl.
22. A method according to Claim 17 in which X is chloro, Y is chloro, n is 1, m is 1, and R and R1 are independently lower alkyl.
23. A method according to Claim 22 in which X is 3-chloro, Y is 4-chloro and R and R1 are each methyl.
24. A method according to Claim 17 in which X and Y are independently selected from the group consisting of chloro and bromo, n is 1, m is 1, R is alkyl and R1 is alkoxy.
25. A method according to Claim 24 in which X is 3-chloro, Y is 4-bromo, R is methyl and R1 is methoxy.
26. A method according to Claim 24 in which X is 3-chloro, Y is 4-chloro, R is methyl and R1 is methoxy.
27. A method according to Claim 17 in which R and R1 taken together is , X is chloro, Y is chloro, n is 1, and m is 1.
28. A method according to Claim 27 in which X is 3-chloro and Y is 5-chloro.
29. A method according to Claim 17 in which R and R1 taken together is , X is chloro, Y is chloro, n is 1, and m is 1.
30. A method according to Claim 29 in which X is 3-chloro and Y is 4-chloro.
31. A method according to Claim 17 in which R and R1 taken together is , X is chloro, Y is chloro, n is 1, and m is 1.
32. A method according to Claim 31 in which X is 3-chloro and Y is 4-chloro.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US55910475A | 1975-03-17 | 1975-03-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1060012A true CA1060012A (en) | 1979-08-07 |
Family
ID=24232283
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA247,999A Expired CA1060012A (en) | 1975-03-17 | 1976-03-16 | N-carbamoyl ethyl oxanilates |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE839691A (en) |
| BR (1) | BR7600981A (en) |
| CA (1) | CA1060012A (en) |
| ES (1) | ES446125A1 (en) |
| IN (1) | IN143984B (en) |
| PL (1) | PL101469B1 (en) |
| SU (2) | SU667097A3 (en) |
| ZA (1) | ZA761011B (en) |
-
1976
- 1976-02-17 BR BR7600981A patent/BR7600981A/en unknown
- 1976-02-19 ZA ZA1011A patent/ZA761011B/en unknown
- 1976-03-05 IN IN404/CAL/76A patent/IN143984B/en unknown
- 1976-03-16 CA CA247,999A patent/CA1060012A/en not_active Expired
- 1976-03-16 ES ES446125A patent/ES446125A1/en not_active Expired
- 1976-03-17 PL PL1976188013A patent/PL101469B1/en unknown
- 1976-03-17 SU SU762333103A patent/SU667097A3/en active
- 1976-03-17 BE BE7000795A patent/BE839691A/en unknown
-
1977
- 1977-01-04 SU SU772434854A patent/SU858560A3/en active
Also Published As
| Publication number | Publication date |
|---|---|
| SU858560A3 (en) | 1981-08-23 |
| ES446125A1 (en) | 1977-10-16 |
| BR7600981A (en) | 1976-09-14 |
| ZA761011B (en) | 1977-01-26 |
| IN143984B (en) | 1978-03-04 |
| PL101469B1 (en) | 1978-12-30 |
| SU667097A3 (en) | 1979-06-05 |
| BE839691A (en) | 1976-09-17 |
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