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Патент USA US3020156

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ice
,_
3,626,1L’l5
Patented Fel:>.~ %, 1%62
2
1
compounds can be named as hydantoic acids or deriva
'
r
3,020,145
“
tives thereof.
-
@RBHZHDAL CGMPOSHTEON AND METHOD
EMPLOYBNG SUBSTITUTED UREAS
‘
‘
The herbicidal compositions of the invention are partic
ularly elfective because of the unique property of the
Richard J. Gobeil, Rayner S. Johnson, and Raymond W. 5 carbamidocarbonyl compounds to translocate in plants
Luckenbaugh, Wilmington, DeL, assignors to E. I. du
after application of the compositions to the foliage of the
Pont de'Nemours and Company, Wilmington, Del., a
unwanted plant. Particularly preferred for this ‘unique
corporation of Delaware
property are compounds of Formula 3 in which A is
No Drawing. Filed Dec. 22, 1955, Ser. No. 554,618
-CH2F—.
I
7 Claims. (Cl. 71-—2.6)
10
Various. methods can be used to prepare carbamido-_
carbonyl compounds used in the herbicidal compositions
This invention relates to herbicidal compositions and
and mehods of the invention. For example, the esters
of the acids represented by Formula 3 above in which R
is hydrogen are conveniently prepared by reacting a
cidal ingredient one or more members of a class of
carbamido alkanoic acids or certain derivatives thereof. 15 carbalkoxyalkyl methylamine with a phenyl isocyanate in
equimolar amounts as shown in the‘ following equation
The carbamido alkanoic acids employed in the herbi
methods. More particularly, it relates to herbicidal com
positions and methods which employ as an essential herbi
cidal compositions and methods of the invention are char
which illustrates the process with respect to speci?c re
acterized by containing the following structure
actants:
(4)
(1)
|
I
——NG(O)NACOOH
20
CHQCOOOQHs
where A represents a bivalent saturated aliphatic hydro
carbon radical containing less than 5 carbon atoms (i.e.,
OH:
0
ethylene, methylene, trimethylene, tetramethylene, ethyl
characterized by having one of the nitrogen valence bonds 25
shown in the formula attached to methyl, another of the
nitrogen valence bonds attached to phenyl or one of a
speci?ed group of substituted phenyl radicals and the re
CH3
ll
idene, a propylidene, and a butylidene) and are further
CIONHd-BIPCHQC 0 o aim
The process of the kind illustrated by Equation 4 is
suitably carried out by adding the amine reactant grad
ually to an agitated solution of the phenyl isocyanate in an
an alkyl or alkenyl radical containing less than 6 carbon 30 inert solvent such as xylene, toluene, or dioxane. The
reaction is suitably carried‘ out at a temperature in the
range of about 50° to 75° C. No catalyst is needed.
More speci?cally, the herbicidal compositions and meth
The alkaline earth and alkali metal salts of acids
ods of the invention are those which employ as an essen
represented by Formula 3 above in which R is hydrogen
tial active ingredient a compound selected from the group
consisting of the carbamido alkanoic acids represented by 35 are obtained .by a modi?cation of the process described
above. An aqueous solution of the carboxyalkyl methyl
the formulas
amine with the alkaline earth or alkali metal hydroxide is
(2)
Xu
brought together with an acetone solution of the phenyl
isocyanate reactant with stirring. Ordinarily, some 1,3
bisarylurea is' formed and this is ?ltered and the ?ltrate
evaporated to dryness whereupon the metal salt is ob
CHK——L\IT—(I%—N—A—C 0 or:
tained usually in the form of a hydrate. The free acids
and
are readily obtained by acidifying metal salts so obtained.
Esters of the acids represented by Formula 3 above
(3)
Xn
R 0 cm
45 in which R is an alkyl or alkenyl radical are prepared by
?rst reacting phosgene with an aniline reactant in an
@iPbLiFA-C 0 on
Y
inert solvent, followed by heating to re?ux until evolution
of hydrogen chloride ceases. The resulting solution of
where A, as de?ned above, is a bivalent saturated ali~
the carbamyl chloride is reacted with the desired sec
phatic hydrocarbon radical containing less than 5 carbon
atoms, R is selected from the group consisting of hydro 50 ondary amine in equimolar amounts in the presence of
gen, alkyl containing less than six carbon atoms and
an acid acceptor such as triethylamine. The following
alkenyl containing less than 6 carbon atoms, X and Y
equations, showing speci?c reactants, illustrate the process:
are selected from hydrogen, halogen, and alkyl contain
ing less than 5 carbon atoms, and n is a positive integer
(5)
(EH3
(liHs
less than 3 (i.e., one or two), the aromatic substituent 55
having hydrogen on at least one of the nuclear carbons
.
w0
CH3
CH3
ortho to the nuclear carbon to which the urea nitrogen
and
atom is linked (in other words, the benzene nucleus
should not contain substituents, other than hydrogen, in
(5a)
.
maining nitrogen valence bond attached to hydrogen or
atoms.
-
‘
H O IQ,
@mwooon —-+ <
both ortho positions); and the salts, esters, and amides 60
of said carbamido alkauoic acids.
For convenience, the class of compounds de?ned and
discussed above will be referredto in a generic sense more
brie?y as carbamidocarbouyl compounds.
'
CH9
|
/
NCCl+HN
<3
I
|
O
CHzCHzCOOCHt
+(czHrlsN —>
-
\ CH3
CH5
The preferred halogen substituent in the carbamido
>Npliol+nol
CH2GH2C O O CH3
carbonyl compounds is chlorine. The preferred alkyl or
monovalent aliphatic radical substituent is methyl or
ethyl, most preferably methyl. And A, in the above for
mulas, is most preferably methylene in which extent the
0
CH3
.
The procedure described above can be used to prepare
3,020,145
3
.
v
4.
40-45n until one equivalent of hydrogen chloride is
evolved. By addition of ammonia gas to the solution the
amide is obtained.
esters of acids represented by Formula 2 above in which R
is a monovalent aliphatic hydrocarbon radical and A, as
de?ned above, is a bivalent saturated aliphatic hydrocar
bon radical, by using the appropriate substituted aniline.
9
()
(!) /CHs
o1
—ITI—O—N\
H
+soo1, —->
011100011
01
H
01
/CH8
NH—~C--N
01110001
or
15
9
( a)
(? /CH3
o1©-Nno-N\
1
20
01
+NH: ———+
(311.0001
IO /CH:
|
onloonni
01
25
The compounds described in Formula (2) can also be
prepared by treating an anhydrous toluene solution of the
Except for the esters, some of which are viscous liquids,
the carbarnidocarbonyl compounds employed in theherbi
sodium salt of an appropriate substituted urea with the
corresponding haloalkylcarboxylic acid ester at 70°-75° 30 cidal formulations and methods of the invention are in
general white crystalline solids. The metal salts are water
C. After heating for about six hours at this temperature,
soluble but the other carbamidocarbonyl compounds are
the product is isolated from the ?ltrate by evaporation of
generally water insoluble and di?er with respect to the
the toluene.
solubility and the common organic solvents, some such as
(7)
35
O
the esters being generally quite soluble and others such as
the acids generally having low solubility.
Herbicidal compositions of the invention are prepared
by admixing one or more of the carbarnidocarbonyl com
pounds de?ned heretofore, in herbicidally effective
amounts, with a conditioning agent of the kind used and
referred to in the art as a pest control adjuvant or modi?er
to provide formulations adapted for ready and e?icien-t
application to soil or weeds =(i.e., unwanted plants) using
Cl
conventional applicator equipment.
~
C O O CzHs
The free acids or salts of compounds of the type de
scribed in Equations (5a), (6a), and (7) can be prepared
45 prepared in the form of solids or liquids. Solid composi
tions are preferably in the form of dusts and are com
pounded to give homogeneous free-?owing dusts by ad
mixing the active compound or compounds with ?nely
divided solids, preferably talcs, natural clays, pyrophyllite,
by hydrolyzing the ester with an equivalent of an alkaline
hydroxide in an aqueous solution. The resultant solution
is extracted with chloroform to remove traces of un
reacted ester or by-product aniline. The solution of the
corresponding alkaline salt can be evaporated to dryness
to obtain the salt or, if desired, the solution acidi?ed to
'
vThus the herbicidal compositions or formulations are
50 diatomaceous earth or flours such as walnut shell, wheat,
redwood, soya bean, cottonseed ?ours and other inert
solid conditioning agents or carriers‘of the kind conven
tionaly employed in preparing pest control compositions
obtain the free acid. The following equation illustrate:
in dust or powdered form.
55
Liquid compositions of the invention are prepared in
the usual way by admixing one or more of the carbamido
carbonyl compounds with a suitable liquid diluent media.
With certain solvents such as alkylated naphthalene, di
methylformamide, and cresol, relatively high, up to about
60 35% by weight or more, concentrations of the carbarnido
carbonyl compounds can be obtained in solution. Other
liquids conventionally used in preparing liquid herbicidal
compositions are for the most part less e?ective solvents.
The herbicidal compositions of the invention whether in
65 the form of dusts or liquids preferably also include a sur
face-active agent of the kind sometimes referred to in the
art as a Wetting, dispersing or emulsifying agent. These
agents which Will be referred to hereinafter more simply
as surface-active dispersing agents cause the compositions
70 to be easily dispersed in water to give aqueous sprays
which for the most part constitute a desirable composition
The amides of the compounds of Formulas 2 and 3 may
be prepared by treatment of the free acids with an equiv
for application.
The surface-active dispersing agents employed can be
of the anionic, cationic or nonionic type and include, for
alent of thionyl chloridein dry toluene is‘ warmed gently 75 example, sodium and potassium oleate, the amine salts of
1
3,020,146
5
6
grinding the mixture" to give a powder having an average;
particle size less than about 50 microns.
oleic acids such as morpholine and dimethylamine oleates,
the sulfonated animal and vegetable oils such as sulfonated
?sh and castor oils, sulfonat 2d petroleum oils, sulfonated
N - (p - chlorophenylcarbamoyl) - N - methyl-?
acyclic hydrocarbons, sodium salt of lignin sulfonic acid
(goulac), alkyl naphthalene sodium sulfonate and other
Wetting, dispersing and emulsifying agents such as those
listed in detail in articles by McCutcheon in “Soap and
Sanitary Chemicals,” August, September, and October of
alanine,
ethyl ester ____________________ ____ I
Fuller’s earth ___________________________ _l__
23.75
‘ Sodium lauryl sulfate, 50% (wetting agent) ____
1
Methyl cellulose, 15 cps. (dispersing agent)_..___
1949.
100
Generally the surface-active agent will not comprise 10
more than about 5 to 15% by weight of the composition
depending, of course, upon the particular surface-active
agent, the system in which it is placed, and the result de
sired, and in certain compositions, the percentage will be
0.25
The Water dispersible powdered composition described
above is dispersed in water to give an aqueous spray com
position containing 0.6% by weight of the active car
ibamidocarbonyl compound which is applied at a dosage
1% or less. Usually the minimum lower concentration 15 of 10 pounds of the carbamidocarbonyl compound per
will be 0.1%.
acre to kill Johnson grass and other unwanted plants.
'
The herbicidal compositions are applied either as a
Example 2
spray or a dust to the locus or area to be protected from
‘A total of 13.1 parts of ?-carbethoxymethylamine is
undesirable plant growth, commonly called weeds, i.e.,
plants growing where they are not wanted. Such appli 20 added gradually over a thirty minute period to an agi
tated solution of 13.3 parts of m-tolylisocyanate in 200
cation can be made directly’ upon the locus or area and
parts of xylene, the temperature increasing during this
the weeds thereon during the period of weed infestation
addition period to about 40° C. Agitation is continued
in order to destroy the Weeds but, if desired, the appli
for another hour and the xylene solvent is then removed
Thus the com 25 by heating under vacuo. There is obtained a 93% yield,
cation can be made in ‘advance of an anticipated weed
infestation to prevent such infestation.
the product N-methyl-N-(m-tolylcarbamoyl)-,B-alanine,
positions can be applied as aqueous foliar sprays but can
ethyl ester, an oily liquid nD25 1.5380.
also be applied as sprays directly to the surface of the
Analysis.——Calc’d for CHI-120N203: N, 10.61. Found:
N, 11.31%.
soil. Alternatively, the dried powdered compositions can
be dusted directly on the plants or on the soil.
The active compound is, of course, applied in amount 30 The compound prepared as above is formulated inv a
liquid or ?uid composition shown below by thoroughly
The
mixing and dispersing the compound and the condition
amount of the active carbarnidocarbonyl compound pres
in'g agents in the organic diluent. '
ent in the compositions as actually applied for destroying,
sufficient to exert the desired herbicidal action.
preventing or controlling weeds will vary with the man
ner of application, the particular weeds for which control 35
N - methyl - N - (m - tolylcarbamoyl) - ,3 - alanine,
is sought, the purposes for which the application is being
Long chain fatty alcohol sulfate (emulsifying agent)
made, and like variables. In general, the herbicidal com
Goulac (dispersing agent) __________________ _.;_
positions as applied in the form of a spray or a dust
Kerosene
‘
ethyl ester _______________________________ __
2
3
_________ __'______________________ __
70
will contain from about 0.5% to 85% by weight of a
carbamidocarbonyl compound or a combination of car 40
bamidocarbonyl compounds.
.
Fertilizer materials, other herbicidal agents, and other
pest control agents such as insecticides and fungicides can
be included in the herbicidal compositions of the inven
tion if desired.
,
_
In order that the invention may be better understood,
the following examples are given in addition to the ex:
100
The liquid formulation of this example is dispersed in
water to give an aqueous emulsion of the composition
containing 8% by weight of the carbamidocarbonyl com
pound.
This aqueous spray composition is sprayed on
45 the area around oil storage tanks at a rate of 50 gallons
per acre of the'spray composition to destroy and ‘control
weeds.
‘
amples already given above. The examples illustrate
'
Example 3
methods for making carbamidocarbonyl compounds, her
Gaseous
hydrogen
chloride
is bubbled into an agi
bicidal formulations employing such compounds, her 50 tated solution of 10 parts of l-(cyanomethyl)-l-methyl—
bicidal applications, and the results obtained. Parts are
3-(m-tolyl) urea in 75 parts ,of methanol. The reaction
by weight. unless otherwise speci?ed and the numbers
is exothermic and the solution warms to re?ux tempera
following tabulated ingredients in the examples represent
ture as the hydrogen chloride is added and ammonium
parts by weight of the ingredients in the combination 55 chloride by-product precipitates. The solution is satu
shown in such tabulation.
' '
rated with hydrogen chloride and then heated at re?ux
temperature for one hour. Ammonium chloride is re
Example 1
moved by ?ltration. The ?ltrate evaporatedto dryness
and then is extracted with benzene from which extract
A total of 19.6 parts of ,B-carbetho-xyethyl methylamine
in 50 parts of xylene is gradually added over a thirty 60 there is obtained a pl-(carbrnethoxymethyl)-1-methyl-3
(m-tolyl) urea, M>.P. 57.5-60.5° c.
minute period to an agitated solution of 23 parts of p
chlorophenyl isocyanatein xylene. The reaction mass
is agitated for an additional hour at about 25° C. and
then diluted with n-penetne. There is obtained an 89%
yield, the product N-(p-chlorophenylcarbarnoyl):N
for
C13H1qC1N2O3:
N,
'
a powdered composition adapted for use in the prepara
tion of a spray using either an oil, Water, or a combina
65 iton of oil and water as a liquid diluent. The powdered
methyl-p-alanine, ethyl ester, M.P. 86—87.5° C.
_ Analysis.—Calc’d
‘
_ The compound prepared as above is formulated in
composition is made by conventional mixing and grind
mg operations.
9.84%.
l-(carbmethoxymethyl)-1-methyl-3-(m-tolyl) urea __' ‘70
Found: N, 9.84%.
The carbamidocarbonyl compound prepared as above 70 Alkylated aryl polyether alcohol (wetting and dis
persing agent) _____________________________ ._t 4
is formulated to provide a Water dispersible powder
adapted for dispersion in water for application as a herbi- ,
cidal spray. The water dispersible powder composition
is made by intimately mixing the ingredients listed below
using conventional mixing or blending equipment and then 1.54
Fuller’s earth ________________ ___ ______________ __ 26
.100,
The dispersible powdered composition of this example
3,020,145
a
8
is admixed with an oil and water to give a spray com
p-chlorophenyl isocyanate reactant of that example with
position containing one part of the powdered composi
phenyl isocyanate.
tion, 80 parts of Water, and 20 parts of alkylated naph
thalene. The resulting spray composition is applied at
the rate of 100 gallons per acre to a ?eld planted with
corn, but prior to emergence of the corn, to control weed
The compound of this example is formulated to pro
vide a water dispersible powder adapted for dispersion
in water for application as a herbicidal spray. The water
infestation of the area.
dispersible powder composition is made by intimately
mixing the ingredients listed below using conventional
mixing or blending equipment and then grinding the mix
'
Example 4
ture to give a powder having an average particle size
A solution of 9 parts of sarcosine in 150 parts of 10 less than about 50 microns.
water is diluted with a solution of 4 parts of sodium
hydroxide in 40 parts of water. A solution of 15.4
3—methyl-5-phenylhydantoic acid, sodium salt mono
parts of. p-chlorophenyl isocyanate in 20 parts of dry
acetone is, added slowly with vigorous agitation to the
Sodium disulfonate-of dibutyl phenylphenol (wetting
hydrate
80:
and dispersing agent) ____________ m _________ __
alkaline sarcosine solution over a ten-minute period. The
mixture is then stirred for one hour at about room tem
Bentonite ______________________________ __, ____ __
perature. 1,3-bis-(p-chlorophenyl)urea which precipi
tates is removed by ?ltration. The ?ltrate'is evaporated
to dryness and there is obtained 24.5 parts of S-(p-chloro
,
181
100
The- water dispersible powdered composition described
20. above is dispersed in water to give an aqueous spray
phenyl)-3-methylhydantoic acid, sodium salt monohy
composition containing 0.6% by weight of the active
drate, a compound which softens at about 128° C. and
carboxyalkylurea which is applied at a dosage of 4 pounds‘
hardens to form a glossy mass.
Analysis.-—~Calc’d for C10H10N2O3ClNa-H2O: N,
9.91%; H2O, 6.37%. Found: N, 9.91%; E20, 6.4%.
The compound prepared as above is formulated in a
dust composition adapted for direct application as a
of said urea per acre as a pre-emergence spray to'crop
land planted with corn to prevent infestation of the
~ planted'area with broad leafed weeds and- grasses.
Example 7
dust. The dust is made by blending or mixing the in
gredients shown below and grinding the mix to give a
composition having an average particle size less than
To a solution of 22' parts of phosgene in 200 parts
of xylene there is added gradually a solution of 35.8
parts of N-phenylglycine, ethyl ester in 25 parts of xylene.
The resulting mixture is heated at about reflux tem
about 50 microns. ‘
5-(p-chlorophenyl)-3-methylhydantoic acid, sodium
perature for 4 hours.
salt monohydrate _________________________ __-_ 2O
After allowing the reaction mass to stand at about
Talc ________________________________________ __ 80
room temperature for approximately 17 hours, 25.5 parts
35 of triethylamine is added to the solution» and then while
100
agitating, 12.4 parts of" dimethy-lamrnonium carbonate is
gradually added.
The dust formulation of this example is applied using
Considerable foaming occurs during
this latter addition.
a conventional dusting apparatus at a dosage of 100
pounds per acre of the composition to a drainage ditch
Triethylamine hydrochloride formed in this process is
removed by ?ltration and the ?ltrate is evaporated to
to kill and inhibit regrowth of weeds.
dryness in vacuum at a pressure <1 mm. Hg.
There
is obtained a 64% yield, the liquid product 3-phenyl-5,5
Example 5
dimethylhydantoic acid, ethyl ester, nD33 1.5228.
Analysis.'—Calc’d for C13H18N2O3: N, 11.27%. Found:
N, 10.83%.
5-( 3,4-dichlorophenyl)~3-methylhydantoic acid, sodium
salt monohydrate, MP. 142-147° C. is obtained in 87%
yield by practicing the process of ‘Example 4 in which
the p-chloroisocyanate of that example is replaced by
The compound prepared as above is formulated in
a dust composition adapted for direct application as a
3,4-dichlorophenylisocyanate.
N,
dust. The dust is made by blending or mixing the in
gredients shown below and grinding the mix to give a
8.83%. Found: N, 8.98%.
A granular herbicidal composition is obtained by mix
ing the compound obtained above in combination with
composition having an average particle size less than
about 50 microns.
Analysis.—Calc’d
for
Cm-H9Cl2N2O3Na-H2O:
the ingredients shown below with water to form a paste.
3~phenyl-5,S-dimethylhydantOic acid, ethyl ester____ 5
The paste is then extruded, dried, and ground to give
Cottonseed
granules of size in the range of about 1,432 to 1%; inch
diameter.
Walnut shell ?our ___________________________ __ 91
oil _________ __ ____________________ __
4
100 >
5-(3,4-dichlorophenyl)-3-methylhydantoic acid, sodi
The dust formulation of this example is applied using
um salt monohydrate ______________________ __V_ 10
Goulac (dispersing agent) ________________ __,_____
3
Hydrocarbon oil ____________________________ __
1
60
Dextrin (binding agent) ______________________ __ 20
Fuller’s earth ______ _; _______________________ __ 66
Example 8
100v
The herbicidal composition of this example is applied
by means of a fertilizer spreader apparatus at a rate of
10 lbs./ acre of the granular formulation to a ?eld planted
a conventional dusting apparatus at a dosage of 15
pounds per acre of carboxyalkyl' urea to prevent growth
of weeds for an extended period.
By the same procedure as outlined in Examples 1 and
65
2, VN-methyl-N-(phenylcarbamoyl)-§-alanine, ethyl ester
(M.P. 43~44° C.) is prepared in 92% yield from ?-car
bethoxyethyl methylamine and phenyl isocyanate.
Analysisrgcalc’d for C13H18O3N2: N, 11.20. Found
N,
11.31.
gence of the cotton plants, to control weed growth in
The carbamidocarbonyl compound prepared as above
70
the planted ?eld.
is formulated to provide a water dispersible powder
Example 6
adapted for dispersion in water for application as a her
bicidal spray. The water dispersible powder composi
3:methyl-S-phenylhydantoic acid, sodium salt mono
tion is made by. intimately mixing the ingredients listed
hydrate, M.P. >300° C., is prepared according to the
below using conventional mixing or blending equipment
procedure of Example 4- by merely substitutingv the
with cottonseed, the application being made prior to emer
3,020,145
10
an average particle size less than about 50 microns.
pared by a procedure likelthat of Example 10. The prod
not is obtained in 80% yield, M.P. 155—158° C.
N-methyl - N - (phenylcarbarnoyl)-,B-alanine, ethyl
Found: N, 10.13.
and then grinding the mixture to give a powder having
ester
Analysis.-Calc’d vfor C1°H10C12N2O3:
_ 75
Fuller’s earth
100
10.2.
The compound prepared as above is formulated in a
dust composition adapted for direct application as a dust.
23.75
Sodium lauryl sulfate, 50% (wetting agent)_____ 1
Methyl cellulose, 15 cps. (dispersing agent)..____ 0.25
N,
The dust is made by blending or mixing the ingredients
shown below and grinding the mix to give a composi
tion having an average particle size less than about 50
microns.
10
The water dispersible powdered composition described
above is dispersed in water to give an aqueous spray
5-(3,4-dichlorophenyl)-3-methylhydantoic acid ____ __ 20
Talc
___ 80
composition containing 0.6% by weight of the active
carbamidocarbonyl compound which is applied at-a dos
100
age of 10 pounds of the carbamidocarbonyl compound 15
per acre to kill Johnson grass and other unwanted plants.
The dust formulation of this example is applied using
Example 9
a conventional dusting apparatus at a dosage of 100
5-(3,4-dichlorophenyl)-3-methylhydantoic acid, ethyl
pounds per acre of the composition to a drainage ditch
ester (M.P. 114—115° C.) is prepared in 90% yield by 20 to kill and inhibit regrowth of Weeds.
the method described in Example 1 from ethylsarcosinate
and 3,4-dichlorophenyl isocyanate.
Analysis.—c?lc’d for C12H1403N2Cl:
Found: Cl, 23.22.
Example 12
C1,
23.2.
By the same procedure outlined in Example 7, a so
“
The compound prepared as above is formulated in
a dust composition adapted for direct application as a
dust. The dust is made by blending or mixing the in
gredients shown below and grinding the mix to give a
composition having an average particle size less than
about 50 microns.
30
5 - ( 3 ,4-dichlorophenyl) -3-methylhydantoic acid, ethyl
ester
Talc
..
_
chloride is prepared from N-methy1-3,4-dichloroaniline.
When this solution is treated with the ethyl ester of sar
cosine in the presence of triethyl amine, 5-(3,4-dichloro‘
phenyl)-3,5-dimethylhydantoic acid, ethyl ester, is ob
tained in 85% yield as a clear viscous oil, nDZS 1.5480
AnalysiS.——Calc’d ‘for C13H16Cl2N2O3: N,
CI,
22.3. Found: N, 8.30; Cl, 22.08.
" '
' The, compound prepared as above is formulated in a
_______ ._ 20
_____
lution of N - (3,4 - dichlorophenyl) - N-methylcarbamyl
liquid or ?uid composition shown below by thoroughly
mixing and dispersing the compound and the condition
80
ing agents in the organic diluent.
100
'
The dust formulation of this example is applied using
5, - (3,4 - diehlorophenyl) 3,5 - dimethylhydantoic
a conventional dusting apparatus at a dosage of 100
acid ethyl ester
pounds per acre of the composition to a drainage ditch
40 Long chain fatty alcohol sulfate (emulsifying agent)
to kill and inhibit regrowth of weeds.
25
Goulac (dispersing agent) ___________________ __
Example 10
Kerosene
By the same procedure as outlined in Example 4, an
aqueous solution of 5~(p-chlorophenyl)—3-methylhydan
toic acid, sodium salt is prepared. This solution is acidi
?ed with 10% aqueous hydrogen chloride. The result
ant precipitate is ?ltered and dried. There is obtained
_________________________________ __
3
70
too
The liquid formulation of this example is dispersed in
water to give an aqueous emulsion of the composition
containing 8% by weight of the carbamidocarbonyl com
pound. This aqueous spray composition is sprayed on
15 parts of S-(p-chlorophenyl)-3-methylhydantoic acid,
M.P. 140~141° C.
Analysis.—Calc’d for C10H11ClN2O3: N, 11.5; Cl,
50 the area around oil storage tanks at a rate of 50 gallons
14.6. Found: N, 11.27; Cl, 14.69.
A granular herbicidal composition is obtained by mix
ing the compound obtained above in combination with
per acre of the spray composition‘ to destroy and control
weeds.
Example 13
the ingredients shown below with water to form a paste.
55
granules of size in the range of about 1/32 to 1%; inch
diameter.
A total of 116.5 parts of 3-(3,4-dichlorophenyl)1,1
dimethylurea is combined with 1000 parts of toluene and
distilled through a packed column until constant head.
S-(p-chlorophenyl)~3-methylhydantoic acid, sodium
temperature is reached to remove all water. The mix
ture is cooled and 28.4 parts of sodium methylate is
The paste is then extruded, dried, and ground to give.
salt _____________________ -2 _______________ _..
10
Goulac (dispersing agent) ____________________ _._
-
3
60. added, and the mixture distilled until constant tempera
ture is again reached.
I
.
After cooling the remaining liquid to 75° C., 87.6
Dextrin (binding agent) ______________________ __ 20
parts of bromoethyl acetate is added gradually. After
Fuller’s earth ________________________________ __ 66
agitating for six hours at 70-75" C., the reaction mix
65 ture is cooled and ?ltered. The toluene is evaporated
100
from the ?ltrate, the residue dissolved in ether, washed
with water, dried over anhydrous magnesium sulfate, and
The herbicidal composition of this example is applied
Hydrocarbon oil _____________________________ __
1
by means of a fertilizer spreader apparatus at a rate of
10 lbs./ acre of the granular formulation to a ?eld planted
then evaporated in' vacuum.
There is obtained 75 parts of 3-(3,4-_dichlorophenyl)
with cottonseed, the application being made prior to 70, 5,5-dimethylhydantoic acid, ethyl ester, an orange oil,
111325 1.5460.
_‘
'
emergence of the cotton plants, to control weed growth
Analysis.-'—Calc‘d for C13H16CI2N2O3: C, 48.91; H,
in planted ?eld;
5.01. Found: C, 47.35; H, 4.90.
.
'
Example 11
The compound prepared as above is formulated in a
5-(3,4-dichlorophenyl)-3emethylhydantoic acid is pre 75, liquid or‘ ?uid composition shown below by thoroughly
3,0120, 14s
12
ll
granules of size in the range of about ‘V32 to
mixing. and dispersing the compound and the condition
ing agents in the organic diluent.
inch di
ameter.
3 - (3,4 - dichlorophenyl) - 5,5 - dimethylhydantoic
acid, sodium salt _________________________ __
Goulac (dispersing agent) ___________________ __
3 - (3,4- - dichlorophenyl) - 5,5 - dimethylhydantoic
acid, ethyl ester-..“ ________________ __'______
25
Long chain fatty alcohol sulfate (emulsifying agent)-
2
Goulac
(dispersing agent) ___- ______________ _a__
Kerosene
10
3
Hydrocarbon oil ____________________________ __
l
Dextrin (binding agent) _____________________ __
20
Fuller’s
66
earth ______________________________ __
__________ _..-_ ____________________ __
10
100
100
The herbicidal composition of this example is applied
by means of a fertilizer spreader apparatus at a rate of
10 lbs./ acre of- the granular formulation to a field planted
The‘ liquid formulation of this example is dispersed in
water to give an aqueous emulsion of the composition 15 with cottonseed, the application being made prior to emer
containing 8% by weight of the carbamidocarbonyl com
gence of the cotton plants, to control weed growth in the
pound. This aqueous spray composition is sprayed on
planted ?eld.
_
the area around oil storage tanks‘ at a rate of 50 gallons
Example 16
per acre of the spray composition to‘ destroy and‘ control
weeds.
3,4-xylylisocyanate is reacted‘ with an equimolar quan
1
tity of 5-carbmethoxyethylmethylamine according to the
Example 14
method described in Example 1 to yield‘ N-rnethyl-N
(3,4-xylylcarbamoyl)-?-alanine, methyl ester. I
A mixture of 20 parts of 3'-(3,4-dichlorophenyl)-5,5
The carbami‘d‘oc'arb'onyl compound prepared as‘ above
dimethylhydantoic acid, ethyl ester, 100 parts of’ water
and 3 parts by weight of. sodium hydroxide is stirred for 25 is formulated to provide a water dispersible powder
adapted for dispersion in water‘ for application as a herb
24 hours at room temperature. The mixture is extracted
icidal spray. The water dispersible powder‘v composition
twice with chloroform and the aqueous layer acidi?ed
is made by intimately mixing the ingredients listed below
with dilute hydrogen chloride. The solid which sep
using conventional- mixing or‘ blending equipment and
arated is puri?ed by recrystallization from ether and n
then grinding the mixture‘ to give a. powder having an
pentane. The pure 3-(3,4-dichlorophenyl)-5,5-dirneth
average particle size less than about 50' microns.
ylhydantoic acidproduct obtained melts at 1795-1815 °
C
.
N-rnethyl-N-( 3 ,4'-xylylc'arbamoyl) v-/8-alanine', meth
w Analysis.—-Calc’d for C11H12Cl2N2O3: N, 9.62; NE.
ly ester ________________________________ __
291. Found: N,-9.39; NE 291.
Fuller’s earth; ____________________________ __
The compound prepared as above is formulated in a 35 Sodium lauryl sulfate, 50% (wetting agent) _____
powdered composition adapted for use in the'preparation
1
Methyl cellulose, 15 cps. (dispersing agent)____ 0.25
of a spray using either an oil, water, or a combination
of oil and water as a liquid diluent. The powdered
100'
composition is" made by conventional mixing and grind
ing operations‘.
75‘
23.75
40
The water dispersible powdered‘ composition described
above is dispersed in water to‘ give an aqueous spray com
position containing 0.6% by weight of the active carb
3 - (3,4"- dichlorophe'nyl) - 5,5‘ - dimeth'ylhydant'oic
acid
_
___
70
Alkylated aryl polyether alcohol (wetting and dis
persing
agent) ___________________________ __
4
earth ________ _g _____ __~_-.;_ ____ __; ____ __
26
45
amidocarbonyl compound which is applied at a dosage of
10 pounds of the'carbamidocarbonyl compound per acre
to kill Johnson grass and other unwanted plants.
Example 17
Phenylisocyanate is reacted with B-carbrnethoxyethyl
methylamine in equimolar portions’ according to the
100
method described in Example 1 to yield N-methyl-N‘-‘
50 (phenylcarbamoyl)-B-alanine, methyl ester.
Thedispersible powdered composition of this example
The compound prepared as above is‘ formulated in a
is admixed with an oil and water to give a spray com
liquid or fluid composition shown below by thoroughly
position containing one part of the powdered composi
mixing and dispersing the compound and the condition-'
tion, 80 parts of water, and 20 parts of alkylated naph~
ing agents-in the organic diluent.
thalene. The resulting spray composition is applied at
N-methyl-N-(phenylcarbamoyl)43-alanine, methyl es
the rate of 100 gallons per acre to a ?eld planted with
Fuller’s
corn, but prior to emergence of the corn, to control weed
infestation of- the area.
ter
______________________________________ __ 25
Long chain fatty alcohol sulfate (emulsifying agent) __
Goulac
Example 15‘
2
agent) ________ __>_ _________ __
‘
Kerosene _'__' ________________________________ __ 70
When 1.45 parts of 3- (3,4-dichlorophenyl)-5,5-di
methylhydantoic acid is combined with 20 parts of a
0.025 molar solution of aqueous sodium hydroxide and
agitated for‘ one hour a solution is obtained.
(dispersing
This so
100‘
The liquid formulation of this example is dispersed in
water to give an aqueous emulsion of the composition
lution is diluted with two’ volumes of ethyl alcohol and
then the entire solution is evaporated to dryness under
containing 8% by weight of the carbamidocarbonyl com
pound. This aqueous spray composition is sprayed on
reduced’ pressure to give 3-(3,4-dichlorophenyl-5,S-di
methylhydantoic acid, sodium salt.
the area around oil storage tanks at a rate of 50 gallons
per acre of the spray composition to destroy and control
Analysis-.~—Calc’d for CuHnClzNzOgNZil N, 8.94; 70 weeds.
NE. 313. Pound: N, 8.46; NE. 318.
A granular‘herhicidal composition is obtained by mix
ing the compound obtained above in combination with
the ingredients shown below with water to form a paste.
The paste is' then‘ extruded, dried-,7 and ground to‘ give
Example 18
Phenylisocyanate is reacted with ?-carbbutoxyethyl
methylamine is equimolar proportions according to the
method described in Example 1 to yield N~methyl~N~
(phenylcarbamoyl)-?-alanine, butyl ester.
3,020,145
14
13
The compound prepared as above is formulated in a
vide a‘ water dispersible powder adapted for dispersion in
powdered composition adapted for use in the preparation
water for application as a herbicidal spray. The water
of a spray using either an oil, water, or a combination of
dispersible powder composition is made by intimately mix
ing the ingredients listed below using conventional mixing
oil and water as a liquid diluent. The powdered compo
or blending equipment and then grinding the mixture to
give a powder having an average particle size less than
about 50 microns.
sion is made by conventional mixing and grinding opera
tions.
N-methyl-N-(phenylcarbamoyl)~?-alanine, butyl es
ter ______________________________________ .._
S-(p-cumyl)-3-methy-lhydantoic acid, sodium salt--- 80
Sodium ,disulfonate of dibutyl phenylphenol (wetting
70
Alkylated aryl polyether alcohol (wetting and dispers
4
and dispersing agent) ______________________ __
2
Fuller’s earth__-_ _____________________________ __ 26
Bentonite ______________ __. __________________ __
18
ing agent)
__
100
100
The dispersible powdered composition of this example
is admixed with an oil and water to give a spray composi
15
The water dispersible powdered composition described
above is dispersed in water to give an aqueous spray com
position containing 0.6% by weight of the active carboxy
tion containing one part of the powdered composition,
alkylurea which is applied at a dosage of 4 pounds of said
80 parts of water, and 20 parts of alkylated naphthalene.
urea per acre as a pre-emergence spray to crop land
The resulting spray compositionis applied at the rate of
100 gallons per acre to afield planted with corn, but prior 20 planted with corn to prevent infestation of the planted
area with broad leafed weeds and grasses.
to emergence of the corn, to control weed infestation of
the area.
.
Example 22
A solution of the ammonium salt of 3-(3,4-d-ichloro
-
Example 19
'3,4-dichlorophenylisocyanate is reacted with 5~methyl
aminovaleric acid, methyl ester in equimolar proportions
according to the method described in Example 1 to yield
phenyl)-5,5-dimethylhydantoic acid is prepared by dis
25 solving in an equimolar quantity of concentrated am
monium hydroxide in 25 parts of water.
5 - [3 - (3,4 - dichlorophenyl) - 1 - methylureidolvaleric
acid, methyl ester.
At.)
The water is
removed by evaporation to obtain the product.
The compound prepared as above is formulated in a
The compound prepared as above is formulated in a
dust composition adapted for direct application as atdust.
dust composition adapted for direct application as a dust. 30 The dust is made by blending or mixing the ingredients
The dust is made by blending or mixing the ingredients
shown below ‘and grinding the mix to give a composition
shown below and grinding the mix to give a composition
having an average particle size less than about 50 microns.
having an average particle size less than about 50 microns.
5 - [3 - (3,4 - dichlorophenyl) - l - methylureidol
valeric acid, methyl ester ____________________ __ 20
3-(3,4-dichlorophenyl)-5,5-dimethylhydantoic acid__
Cottonseed oil
___
, 5.
‘4
Walnut shell ?our ___________________________ __
91
Talc _______________________________________ __l 80
100
. 100
g The dust formulation of this example is applied using
The dust formulation of this exampleis applied using a 40 a conventional dusting apparatus at a dosage of 15 pounds
conventional dusting apparatus at a dosage of 100 pounds
per acre of carboxyalkyl urea to prevent growth of weeds
per acre of the composition to a drainage ditch to kill
for an extended period.
and inhibit regrowth of weeds.
Example 20
'
.
45
The procedure as described in Example 4 is followed,
Example 23
An equimolar quantity of methylamine gas is used in
the. procedure described .in- Example 7 to react with the
substituting 6.6 parts of potassium hydroxide (85% pure)
carbanilylchloride to prepare S-methyl-3-phenylhydantoic
acid, ethyl ester.
for the sodium hydroxide of that example, to prepare 5
(p-ch‘lorophenyl)~3-methylhydantoic acid, potassium salt.
The carbamidocarbonyl compound prepared as above
is formulated to provide a water dispersible powder
adapted for dispersion in water for application as a
herbicidal spray. The water dispersible powder com~
A granular herbicidal composition is obtained by mix
ing the compound obtained above in combination with the
ingredients shown below with water to form a paste. The
paste is then extruded, dried, and ground to give granules
position is made by intimately mixing the ingredients
of size in the range of about 1/32 to 1%. inch diameter.
listed below using conventional mixing or blending equip
ment and then grinding the mixture to give a powder hav
ing an average particle size less than about 50 microns.
S-(p-chlorophenyl)-3-methylhydantoic acid, potassium
salt ______________________________________ __
10
Goulac (dispersing agent) _____________________ __
3
S-methyl-3-phenylhydantoic acid, ethyl ester_____ 75
Hydrocarbon nil
1
Fuller’s
'
_____
Dextrin (binding agent) ______________________ __ 20
60
Fuller’s earth ________________________________ __ 66
100
’ The herbicidal composition of this example is applied
earth____'_ ______________ _'_ _______ __
23.75
Sodium lauryl sulfate, 50% (wetting agent)_____
Methyl cellulose, 15 cps. (dispersing agent)_____
1
0.25
100
The water dispersible powdered composition described
by means of a fertilizer spreader apparatus at a rate of 65 above is dispersed in water to give an aqueous spray com
10 lbs./ acre of the granular formulation to a ?eld planted
position containing 0.6% by weight of the active carbami
with cottonseed, the application being made prior to
docarbonyl compound which is applied at a dosage of 10
pounds of the carbamidocarbonyl compound per acre, to
kill Johnson grass and other unwanted plants.
emergence of the cotton plants, to control weed growth.
in the planted ?eld.
Example 21
70
Example 24
When p-cumylisocyanate (16.1 parts) is. used as the
isocyanate in the method described in Example 4,
_ An equimo-lar quantity of n-butylmethylamine is used
S-(p-cumyl)-3-methylhydantoic acid, sodium salt is
in the procedure described in Example 7 to react with
obtained.
the carbanilylchloride to prepare S-n-butyl-S-rnethyl
I
The compound'of this example'is formulated to .pro 75
=3_-phenylhyd_antoic acid, ethyl ester.
_
"
3,020,145‘
1%
l5
mixing and dispersing the compound and the conditioning
The compound prepared as above is formulated in a
dust composition adapted for direct application as a dust.
agents in the organic diluent.
The dust is made by blending or mixing the ingredients
shown below and grinding the mix to give a composition
2-[3-(3,4 - dichlorophenyl) - 1 - methylureido]acet
amide _____
25
having an average particle size less than about 50 microns.
Long chain fatty alcohol sulfate (emulsifying
S-n-butyl-S - methyl - 3 - phenylhydantoic acid, ethyl
Goulac (dispersing agent) ____________________ __
3
Kerosene __________________________________ __
70
agent) _
ester ________ __- ___________________________ __
20
Talc ____ _.; _________________________________ __
80
10’
100
100
The liquid formulation of this example is dispersed in
water to give an aqueous emulsion of the composition
The dust formulation of this example is applied using
containing8% by weight of the carbamidocarbonyl com
a conventional dusting apparatus at a dosage of 100
pound. This aqueous spray composition is sprayed on the
15'
pounds per acre of the composition to a drainage ditch to
area around oil storage‘ tanks at a rate of 5G gallonsper
kill and inhibit regrowth of weeds.
acreof the spray composition to destroy and control
Example 25
3-anilinoprop-ionic' acid, dodécyl ester (66.6 parts) is
Weeds.
Example 28
reacted as described in Example 7 to yield 3-(1-phenyl
To a solution of 22 parts of phosgene in 200 parts of
xylene there is added gradually a solution of 35.8‘ parts
3,3-dimethylureido)-propionic acid, dodecyl ester.
A granular herbicidal composition is obtained by mix
ing the compound obtained above in combination with
the ingredients shown below with water to form a paste.
of N-phenylglycine, ethyl ester in‘ 25 parts of xylene. The
resultant mixture is heated at re?ux temperature for four
The paste is then extruded, dried,- and ground to give
hours.
granules of size in the range of- about 1/1,? to 1%; inch
diameter.
3-(1- phenyl - 3,3 - dim'ethylureido) - propionic acid,
30'
dodecyl ester _____________________________ __
l0
Goulac (dispersing agent) ____________ __'__;_-___
3
I
I
I
I
_I
I
II
ter cooling the reaction mass, 25.5v parts‘ of triethyl
amine is added, and then 14.2 parts of N-methylallyl
amine is added gradually. The tn'ethylamine hydro
chloride is removed .by ?ltration and 5-allyl-5-Irnethyl-3
phenylhydantoic acid, ethyl ester is isolated by evapora‘
tion of the solvent in vacuum at a pressure of less than
1 mm. Hg.
I _
p
The compound prepared as above is formulated in a
Dextrin' (binding agent)’ ________________ _>____'__. 20
dust composition adapted for direct application as a' dust.
Fuller’s earth _______________________________ __
66' 351 The dust is made‘ by blending or mixing the‘ ingredients
shown below and‘ grinding the mix to give a’ composition
100
havingv an average particle size lessv than about 50 microns.
Hydrocarbon oil ____________ -_-_____'__'__' ____ -->.
1
The herbicidal composition of this example is applied
5-allyl-5-methyl-3-phenylhydantoic acid, ethyl ester__
5
Cottonseed oil-
4
____ __
by means of a fertilizer spreader apparatus at a ‘rate of’ 40 Walnut shell ?our ________________ __'___'__'___‘_"_._
10 lbs./ acre of the granular formulation to'a ?eld planted
100;
with cottonseed, the application being made prior to
emergence of the cotton plants, to control weed growth in
the planted ?eld.
Example 26
S-p-chloroanilinovzileric acid, ethyl ester (51.1 parts) is
reacted‘ as dissolved in Example 7 to yield 5'-[1-(p-chloro
91
The dust formulation of
example is applied using
. a conventional dusting apparatusat a‘dosage of 15 pounds
per acre of carboxyalkyl urea to prevent growth of weeds
for an extended period.
Example 29v
phenyl)-3,3-dimethylureido]valeric acid, ethyl ester.
By the same procedure as outlined in Example 28, 5
The compound prepared as above isformulat‘ed in a
dust composition adapted for direct application as a dust.
allyl-3-(3,4-dichlorophenyl) -5-methylhydantoic acid, ethyl
The dust. is‘ made by blending or mixing the ingredients
ester is prepared from an equal molar quantity of N-(3,4
shown below and grinding the mix to give a composition
having an average-particle size less than about 50 microns.
dichlorophenyl)-glycine, ethyl ester.
I
The compound prepared as above is formulated in a'
- liquid or ?uid composition shown below by thoroughly
S-[l-(p-chlorophenyl) - 3,3 - dimethylureido1valeric
acid, ethyl ester ___________________________ __
20
Talc _______________________________________ __
80
mixing and dispersing the compound and the conditioning
agents in the‘ organic diluent.
5-allyl-3-(3,4-dichlorophenyl) - 5 - methylhydantoic
acid, ethyl ester
25‘
100 60 Long chain fatty alcohol sulfate
agent)
____
Goulac (dispersing agent) ____________________ __
The dust formulation of this example is applied using
Kerosene
a conventional dusting apparatus at a dosage of 100
pounds per acre of the composition to a drainage ditch to
kill‘and inhibit regrowth of Weeds.
_____ _._
(emulsifying
65
_
3
70
100
Example 27
A dry toluene solution 100 parts of 5-r(3,4-dichloro—
phenyl)-3-methylhydantoic acid is warmed gently at 40
The liquid formulation of this example is dispersed in
chlorophenyl) -1-methylureido] acetamide is prepared.
Example 30
By the same procedure as outlined‘in Example 28, 3
water to give an aqueous emulsion of- the composition
containing 8% by weight of the carbamidocarbonyl com
pound. This aqueous spray composition is sprayed on
70
45° C. with an equimolar equivalent of thionyl chloride
the area around oil storage tanks at a rate of 50 gallons
until one equivalent of hydrogen chloride evolves. By
per acre of the spray composition to destroy and control
addition of ammonia gas to the solution, 2-[3-(3,4-di
weeds.
The compound'prepared as above is formulated in‘a
liquid or fluid composition .shown'below by thoroughly
8,020,145
17
'
While the invention has been described with particular
reference to speci?c embodiments, it will be appreciated
that nounnecessary limitationsare tobe understood there
(3-allyl-3-methyl-1-phenylureido) 'propionic‘ acid, ‘ethyl
ester is prepared from an equal molar quantity of 3-(3,4
dichloroanilino)-propionic acid, ethyl ester.
The compound prepared as above is formulated in a
dust composition adapted for direct application as a dust.
from. The invention is not limited to the exact details
shown and described for obvious modi?cations will occur
The dust is made by blending or mixing the ingredients
shown below and grinding the mix to give a composition
to those skilled in the art.
'
' This application is a continuation in pan" of our 'co
pending application Serial No. 505,534, ?led May 2, 1955,
having an average particle size less than about 50 microns.
now abandoned.
3-(3-allyl~3-methyl - l - phenylureido)propionic acid,
ethyl
ester
‘
510
I
Cottonseed oil___
'
Walnut shell ?our ___________________________ __
'
We claim?
.
-
_
l. A method for the control of weeds-which comprises
4
91
applying to a locus to be protected, in amount su?‘lcient
to exert a herbicidal action, a compound selected from the
100
group consisting of the carbamido alkanoic acids repre
sented by the formulas
The dust formulation of this example is applied using
15
a conventional dusting apparatus at a dosage of 15 pounds
per acre of carboxyalkyl ureato prevent growth of weeds .
for an extended period.
20
Example 31
and
A solution of N-allyl-N-(3,4-dichlorophenyl)-carbamyl
chloride is prepared from N-allyl-3,4-dichloroaniline by
the procedure described in Example 28. When this solu
tion is treated with the ethyl ester of sarcosine in the 25
presence of triethylamine, 5-allyl-5-(3,4-dichlorophenyl-3
methyl hydantoic acid, ethyl ester is obtained.
where A is a bivalent saturated aliphatic hydrocarbon
radical containing less than 5 carbon atoms, R is selected
The compound prepared as above is formulated in a
from the group consisting of hydrogen, alkyl containing
liquid or ?uid composition shown below by thoroughly
mixing and dispersing the compound and the conditioning 30 less than 6 carbon atoms and alkenyl containing less than
6 carbon atoms,‘ X and Y are selected from the group
agents in the organic diluent. "
' ‘
‘
consisting of hydrogen, halogen, and alkyl containing less
5-allyl-5-(3,4-dichlorophenyl) é 3 - methyl hydantoic
"than 5 carbon atoms, and n is a positive integer less than
_3, the aromatic substituent having hydrogen on at least
one of the nuclear carbons ortho to the nuclear carbon to
235 which the urea nitrogen atom is linked, and the salts,
acid, ethyl ester
Long chain fatty alcohol sulfate (emulsifying
agent)
'
Goulac (dispersing agent) ____________________ __
3
Kerosene __________________________________ __
70
esters, and amides of said carbamido alkanoic acids.
’‘ 2. A herbicidal composition comprising a material se
lected from the group consisting of anionic, cationic and
nonionic surface active agents and, in amount su?icient
1 100
The liquid formulation of this example is dispersed in
go, to exert herbicidal action, a compound selected from the
group consisting of the carbamido alkanoic acids repre
water to give an aqueous emulsion of the composition
sented by the formulas
containing 8% by weight of the carbamidocarbonyl com
pound. This aqueous spray composition is sprayed on
>
'
the area around oil storage tanks at a rate of 50 gallons
per acre of the spray composition to destroy and control 45
Weeds.
Illustrative of other compounds which can be similarly
prepared, formulated, and applied by the method de
scribed heretofore are:
N-methyl-N-(phenylcarbamoyl)~B-alanine, ?-chloroethyl
ester
50
'
5-(p-chlorophenyl)~3-methylhydantoic acid, butyl ester
where A is a bivalent saturated aliphatic hydrocarbon
3 -methyl-5- ( 3,4-xylyl ) hydantoic acid
5 —(p-isopropylphenyl)-3-methylhydantoic acid
3-(p-chlorophenyl)~5-methylhydantoic acid
3-(-chlorophenyl)-5,5-dimethylhydantoic acid, ethyl ester
55 radical containing less than 5 carbon atoms, R is selected
3 - ( 3,4-dichlorophenyl) -3 -n-butyl-S-methylhydantoic acid,
‘butyl ester
6 carbon atoms, X and Y are selected from the group
5- (p-chlorophenyl)—3,5-dimethylhydantoic acid, ethyl ester
S-n-butyl-S- ( 3,4~dichlorophenyl) ~3-methylhydantoic acid,
N- (p-chlorophenylcarb amoyl) -N-methyl-3 -methyl-/8-'
alanine, ethyl ester
_
2— [ l- ( p-chlorophenyl ) -3 ,3-dimethylureido] acetamide
5-(p-chlorophenyl)-3-methylhydantoic
acid,
salt
less than 6 carbon atoms and alkenyl containing less than
consisting of hydrogen, halogen, and alkyl containing less
60 than 5 carbon atoms, and n is a positive integer less than
3, the aromatic substituent having hydrogen on at least
one of the nuclear carbons ortho to the nuclear carbon
to which the urea nitrogen atom is linked, and the salts,
methyl ester
5-(3-p-chlorophenyl-l~methy1ureido)valeric acid
5-( 1-p-chlorophenyl~3,3-dimethylureido)valeric acid
from the group consisting of hydrogen, alkyl containing
esters, and amides of said carbamido alkanoic acids.
3. A herbicidal composition comprising a material se
65
lected from the group consisting of anionic, cationic and
nonionic surface active agents and, in amount sufficient
to exert herbicidal action, the compound 5-(3,4-dichloro
of
“Dowex” 50, a quaternary ammonium type ion ex
phenyl)-3-methyl hydantoic acid, sodium salt monohy
change resin made by reaction of chloromethylated 70 drate.
4. A herbicidal composition comprising a material se
polystyrene with tertiary aliphatic amine
lected from the group consisting of anionic, cationic and
S-(p-chlorophenyl)-3-methylhydantoic acid, salt of
nonionic surface active agents and, in amount sufficient
“Amberlite” IR4B, weak base anion exchange resin
to exert herbicidal action, the compound 3-(3,4-dichloro
made by the reaction of meta-phenylenediamine and
75 phenyl)-5,5-dimcthyl hydantoic acid, ethyl ester.
formaldehyde
3,020,145
19,
20
5. A herbicidal composition comprising a material se
of the‘ carbamido alkanoic acids represented by the
lected from the group consisting of anionic, cationic and
nonionic surface active agents and, in amount suf?cient
to exert herbicidal action, the compound S-(p-chloro
formulas
phenyl)-3-methyl hydantoic acid, sodium salt monohy
drate.
O
6.-A herbicidal composition comprising a powdered
solid inert carrier material and, in amount su?icient to
and
exert herbicidal action, a compound selected from the
group consisting of the carbamido alkanoic acids repre~ 10
Xn
sented by the formulas
R Ov CH:
1323- Lb-alI-A-oo OH
where A is a bivalent saturated aliphatic hydrocarbon
15 radical containing less than 5 carbon atoms, R is selected
‘from the group consisting of hydrogen, alkyl containing
less than 6 carbon atoms and alkenyl containing less than
6 carbon atoms, X and Y are selected from the group
consisting of hydrogen, halogen, and alkyl containing less
and
20 than 5 carbon atoms, and n is a positive integer less than
3, the aromatic substituent having hydrogen on at least
one of the nuclear carbons ortho to the nuclear carbon
to which the urea nitrogen atom is linked, and the salts,
esters, and amides of said carbamido alkanoic acids.
v25
‘where A is a bivalent saturated aliphatic hydrocarbon
radical containing less than 5 carbon atoms, R is selected
from the group consisting‘ of hydrogen, alkyl containing
less than 6 carbon atoms and a'lkenyl containing less than
6 carbon atoms, X and Y are selected from the group _
consisting of hydrogen, halogen, and alkyl containing less
References Cited in the ?le of this patent
UNITED STATES PATENTS
2,572,568
Glues‘e‘nkarnp ________ __ Oct. 23, 1951
2,655,445
2,704,245
Todd ________________ __ Oct. 13, 1953
Sear'le ______________ __ Mar. 15, 1955
2,705,195
Cupery et a1. ________ __ Mar. 29, 1955
Ryker'et a1. "a _______ .... May 31, 1955
Todd _________________ _. Nov. 8, 1955
than 5 carbon atoms, and n is a positive integer less than
2,709,648’
3, the aromatic substi'tuent having hydrogen on at least
2,723,192
one of the nuclear carbons ortho to the nuclear carbon
2,726,150
35
to which the urea nitrogen atom is linked, and the salts,
2,782,112
esters, and amides of said carbamido alkanoic acids.
7. ‘A herbicidal composition comprising a hydrocarbon
liquid diluent and, in amount su?icient to exert herbicidal
action, a compound selected from the group consisting
Wolter ________________ __ Dec. 6, 1955
Gilbertet a1 ___________ ._ Feb. 19, 1957 7
OTHER REFERENCES 7
Petersen et al.; in “Chemical Abstracts,” vol. 43, col
umns 168 and 169, 1949.
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