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Патент USA US2412510

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2,412,510
Patented Dec. 10, 1946
'
2,412,510 '
'. vHmrrnonsmcomosmons
» xnmcwms -.
FOB
‘Q
‘
Franklin D.,V.Ion_es, maataaamiya
,
‘
~ I
American Chemical Paintcompany, Ambler,
Pat, a corporation of Delaware
'
‘No Drawing. vApplication June 21, 1945, vSerial -
vN0. 600,841. In Canada June 2, 1944
,
1
"
'
220mm.
(c1. 187-45)
' include-both the
1 ‘The present vinventionrelates ‘to
compositions for killing growing weeds. ,-
. ~
; The term "weed’? is used in the present disclo
sure in its broadest sense, namely, a plantwhich
persists in growing where it is not wanted. ‘This
use of theterm is broad enough to include not
acids.
For practicalreasonsr'acids having one to nine
carbon atoms are preferred, but the invention is
not restricted thereto. ; As . examples of suitable
. acids-may be mentioned formic, acetic, propionic, '
butyric, valeric, hexoic, acrylic, methyl'acrylic,
only plants harmful to man or, animal, such; as
those of the Rhus family (poison ivy and poison
etc.
oak), bindweed, and plants such aswild garlic
found particularly suitable for the purposes of
..
As examples-of- compounds,~:which;haveibeen '
and Frenchpweed, which have a bad e?ect on 10 this invention maybe mentioned the amides and
dairy, products, but also otherwise desirable
plants suchas-Japanese honey suckle or lawn
thioamides of the following acids-z,
.
.
,- »
Benzoic acid (phenylformic acid), itshalogen
- Weeds, as a general rule, are able to grow un
and nitro-substitution- products such as, 2.4-di- 1'
chloro-benzoic' acid, :2.5-dichloro-.benzoic , acid,
der adverse conditions and their control presents
a very di?lcult and troublesome problem to farm
acid, 2,-chloro-5-nitro-benzolc acid, and Z-bromor
grasses growing ‘on driveways.
\
-
'
ers. Prior to the research which resulted in the‘
3.5-dich1oro-benzoic ‘acid, . 2.3.5-triiodov benzoic
3-nitrobenzoic acid.
J
.-
v,
-
.
»
Phenyl acetic acid,,its halogen substitution '
present invention, the most effective methods-in
volved the use of chemicals such as common salt,
products such as-Z-chloro-phenyl acetic acid,
carbon disulphide, ammonium sulfamate, sodium _
acetic acid, and li-iodo-phenylacetic'acid. '
dinitro-ortho-cresylate, sodium arsenite, and oil,
All of these materials are low in unit cost, but
Phenyl alpha and gamma butyric acids, and
their various derivatives, particularly 4-chloro- ' I
chlorates,v iron sulphate, ammonium sulphate, 20 4-chloro-phenyl acetic .acid, "4-bromo-phenyl
phenylalpha‘and gammabutyric acids," .
high in cost per acre when applied in su?icient
quantities to kill the weeds and they may steril 25 Phenoxyacetic acid; its alkyl substitution prod
ize the soil for long periods. Moreover, many of
them are hazardous, being poisonous or explo
sive, or both. Most of them are corrosive to the
equipment and difficult - to handle.
Moreover,
ucts such as 4-methy1 phenoxyacetic acid, 2.4
dlmethyl phenoxyacetic acid, 3.4-dimethyl phen
oxyacetic acid, 3.5-dimethyl phenoxyacetic acid,
and 2.4.5-trimethyl phenoxyacetic acid, its al
they tend'to kill the top of the plant without
killing the roots permanently.
The primary object of the invention is to im
koxy derivatives such as 4-methoxyphenoxy
acetic acid, its halogen substitution products, such
as 2-chloro-phenoxyacetic acid, 4-chloro-phen
prove chemical methods for eradicating weeds in
oxyacetic acid, 2.4-dich1oro-phenoxyacetica acid,
2.4.5-trichloro-phenoiwacetic acid, 72.4.6-trichlo
ro-phenoxyacetic acid, 2.3.4.6-tetrach1oro-phen
an active state of growth.
.
Another object of importance is to provide a 35
oxyacetic acid, pentachloro-phenoxyacetic acid,
wholly new‘ class of systemic or translocated
herbicides.
-
4-bromo-phenoxyacetic acid, 2.4-dibromo—phen
oxyacetic acid, 2.4.6-tribromophenoxyacetic acid,
Another important object is to provide compo
4-iodo-phenoxyacetic acid, 4-?uoro-phenoxy
sitions for the purpose of eradicating growing
weeds, which are considerably less expensive, 40 acetic acid and 2.4-di?uoro-phenoxyacetic acid,
and its nitro-substitution products such as 4-m
more economical, safer to use, and more eifective
tro-phenoxyaceticiacld. As additional examples.
than previously used chemicals.
\
The invention is based in part upon‘the ob‘
servation or discovery that certain compounds,
which will hereinafter be referred to, as “com
pounds of the. invention” at certain concentra
tions, are systemic poisons for higher plant life,
and may be used as the active ingredients of
of suitable derivatives of phenoxyacetic acid may
be mentioned 3-methyl-4-chloro-phenoxyacet
amide, 2-methyl-4-chloro-phenoxyacetamide and
the corresponding thioamides;
.
Phenylimino-acetic acid (phenyl glycine) and
phenylmercaptoaacetic acid, and ‘their haloge
nated products such as 2.4-dichloro-phenylimino
The compounds of the invention are the, amides 50 acetic acid, 4-chloro-pheny1mercapto-acetic acid,
herbicides.
yimercapto, phenylimino, naphthyl, naphthoxy;
and 2.4-dichloro-phenyl-mercapto-acetic acid,
Naphthalene-l-acetic acid, itsalkyl substitu
naphthylmercapto, naphthylimino, and anthra
tion products such as 2-methyl-naphthyl-1
and the thioamides of the phenyl, phenoxy,'phen
acetic acid and é-methyl-naphthyl-l-acetic acid,
cyl, monocarboxylic aliphatic acids.
The term "aliphatic acids” is broad enough to 55 the halogen substitution products such as 4-ch1o
2,412,1510
3
4 ,.
ro-naphthyl-l-acetic acid, and'the nitro-substi
acetic acid.
'
~
.
'
the problems solved by the present invention was
to find a way for getting the insoluble compounds
of the invention into. solution or suspension, so
' as tow-render it possible to bring the necessary
-
l-‘naphthoic acid, z-naphthoic acid, and the
halogen substitution products.
‘
standards of solubility are concerned. One of
l-naphthalene-alpha-propionic acid, l-naph
thalene-beta-propionic acid. l-naphthalene
gamma-butyric acid,‘ andltheir halogen substi
a
v
Most 01 the compounds of the invention ar
practically insoluble in water as far as usual
tution derivatives such as 4-nitro-naphthyl-l
tution products.
..
concentration to bear on the plant tissue.
The present invention is based in part upon the
.
l-naphthoxyacetic acid, 2-naphthoxyacetic 10 observation or discovery that wetting, dispersing
acid, l-naphthoxy-alpha-propionic acid, i-naph
and emulsifying agents in general will dissolve or
thoxy-alpha-propionic acid, and their halogen
suspend from 1 to 50% of their weight oi.’ the
substitution products such as 2-chloro-i-naph
thoxyacetic acid and 2.4-dichloro-1-naphthoxy
acetic acid.
The naphthyl glycines, e. g. l-naphthylimino
compounds of the invention and that when such
solutions or suspensions are mixed with water in
15 any proportion, a relatively stable colloidal sus
pension or solution is formed.
acetic acid and 2-naphthylimino-acetlc acid, and
In this connection, it should be noted that gen
erally speaking it is not possible to produce stable
chloro-l-naphthylimino-acetic acid.
'
solutions of the water-insoluble compounds of the
i-naphthylmercapto-acetic acid and 2-naph 20 invention by dissolving in organic solvents those
thylmercapto-acetic acid, their halogen substi
compounds that happen to be soluble in such sol
their halogen substitution products such as 4
tution products, and the esters and salts.
Tetralyl-B-acetic acid.
_
vents, and then diluting with water. For the ad
dition of water ordinarily precipitates the com
.
Anthracyl-acetic acid, and its halogen substi
tution products.
‘
I
pounds.
25
,
'
This invention is not limited in its broad as
pects to any particular wetting, dispersing or
The foregoing list is given by way or illustra
tion only, and the corresponding derivatives of
emulsifying agent. See, for instance “A List of
the corresponding unsaturated acids, e. g. acrylic
Commercially Available Detergents, Wetting, Dis
persing and Emulsifying Agents" by H. L. Cupples,
acid and its homologues, may be used.
Some, but not. all of the foregoing compounds, 30 Division‘ of Insecticide Investigations of the
United States Department of Agriculture pub
are plant hormones; i. e. they serve to promote
plant growth, when used in very minute ctmcen
lished June, v1940, and chapter 11 on "Emulsions"
trations in the form of solutions or dusts, or in
of Mattiello’s "Protective and Decorative Coat
considerably higher concentrations in the form of
ings,” vol. IV, John Wiley 8; Sons, Inc., New York,
pastes in such materials as fats or greases (e. 8, 35 1944. Nor is the invention in its broad aspects
lanolin). For the purposes of the present inven
limited to agents of either the ionic or non-ionic
type, though I do prefer to use those of the non
tion, the aforementioned compounds, whether or
not they are plant hormones, must be used in
ionic type.
much higher concentrations than have ever been
Agents of the non-ionic type are those that are
used for plant growth promotion. The mini 40 not ailected by salts, acids, or bases. whereas those
mum effective concentration depends upon a
number of factors such as, for instance, the par
ticular species of plant to be eradicated, the par
ticular type of vehicle or medium, and whether or
not an adjuvant is used. There is no upper limit
to the concentration, except that dictated by econ
omy.
If the active herbicidal ingredient is used in an
aqueous medium without an adjuvant having pen
etrating properties, the lower effective limit ap
“pearsto be about .05%. If an adjuvant is used,
"e'. 'g. the wetting, dispersing or emulsifying agents
of the ionic type are aifected to the extent that
precipitation may occur when a salt, acid or base
is added to a solution or suspension of a compound
in an ionic agent.
Sulphonated vegetable oils (e. g. Sulphonated
castor oil, corn oil, peanut oil, soy bean oil, etc.)
are examples of ionic agents that I may use.
These have the advantage of cheapness, but be
ing ionic, they have their limitations when used
in the presence of acids, bases and salts. When
such agents are used, it is advisable to use dis
tilled or soft water for dilution purposes.
As previously stated, agents of the non-ionic
type are preferred. This type of agent will usu
least .1% concentration, whether or not an ad- - - ally dissolve or suspend from 1 to 50% of its
volume or weight of the compounds of the inven_
juvant‘ is employed. If the compound is used in
tion, and may then be diluted with water to the
the form of dusts, I prefer to use concentrations
desired concentration for application to the
of .2% or over. Considerably higher concentra
tions are generally required, if the compounds are
plant. The usual amounts of salts, acids, or al
applied in the form of pastes, mists or aerosols. 60 kalis apparently have little, if any, effect on the
resulting solution or suspension.
' It is to be noted at this point that the effective
ness of the compounds of the invention appears to
A class of non-ionic agents that I have found
particularly suitable for the purposes of this in
be due in large measure to the fact that they
have the property of being able to penetrate into
vention may be de?ned as follows:
the conducting tissue of the plant, being carried
“A water-soluble, non-ionic emulsifying agent
deep into the roots, killing the plant throughout.
containing polyether groups of the formula R. O.
It is well known that in order for a herbicide to
(C2I'I40)n-Rl, where R is an alkyl, aryl, aralkyl,
be fully effective, the herbicide must kill the roots
alkyl-aryl or acyl group of 10 carbon atoms or
as well as the top of the plant.
more, and R1 isan alkyl, aryl, aralkyl, alkyl
> to ‘be mentioned, the lower limit appears to be
in the neighborhood of .02%. I prefer to use at
The compounds of the invention, therefore,
aryl, or acyl group or a hydrogen atom, and n is
appear to ?t the de?nition oi "translocated" or
an integer greater than 2 and generally greater
than 10.”
Two commercial products answering to the
foregoing description, which have been used in
"systemic” herbicides. For they do not merely
injure the weed at the point 01' contact; they
take the normal path from leaves to roots within
, the plant and destroy it from within.
' practicing the invention, are Tween #20 made by
2,412,510
.5
'
4
\
' citric acid was-added.
Atlas Powder Company; Wilmington, Delaware,
and Triton NE made by norm and Haas 60., Phil- ,
vadelphia. Pennsylvania.“ Tween is a polyoxyal-v
up such chemicals ‘much more readily-at. ‘a pH
oi. torless.v Anrwid, may
nlene ‘derivative ‘oi’w sorbitan monolauric, and
Triton NE is apolyalkylene ether‘alcohol.
similarly useful are the polyethyleneglycols
venientto use i'or
purpose ,thanzthe liquid
acids. The acid maybe added at any tlmeberore
using the compositionhbutr-it preferably terms
on the market under the tracle-markv Carbowax.
' The following are several illustrative examples
the teachine'sfoi' the present invention:
{but solid
acids as tartaric, succin'icucitric. malic,,maleic.
suliamic ,and-iumaric are‘ generally more" con
oi molecular weight M17590 or more, ‘obtainable
of? herbicidal compositions made v according to
purpose-tistoiower
the pH, salt has beeniound _that plants take
71.0
part oi’ the stock solution.
a
compounded theinventlonmar
incorporated into
be
compositions containing
other active or inactive ingredients. ‘t.- For in
5
stance, a suitable dry compositionmaycontain
. 5 a
Tween #20 or Triton NE ..... __' .......... ___ _50
any one or more of they compounds of the inven
tion'. a wetting agent in dry formsuch as Alhanol
The three ingredients ‘are thoroughly mixed
sodium > alkylnaphthalenesulphonate), and an
to produce a stock solution. The ‘solution may
acidifying agent, such ascitricgtartariasuccinic,
Phenylacetamide vExample!
_____________ ___
- .... _..'-____
.‘
Butyi'alcohol
(sodium tetrahydronaphthalenesulphonate; or
be diluted with 940 parts or water when it is to 20 malic, maleic, Iumaric and,suliamic acid._ The
purpose of the acid is .toireduce the pH‘to‘ 4
beused.
_'
a
‘
‘
or‘less, at ‘which pH the herbicidal compositions
Example II _
Naphthylthioacetamide or
are more readily absorbed; by the plant. - An
acid, either solid or liquid, may also be added
2.4-dichlorophen
oxyacetamidev ‘is used- instead
acetamide of Example 1.‘
_ of) the
phenyl- _
to the wet compositions. ._It isadvantageous in
many cases to add; a'buiier salt (a salt oi‘any
Example’ III
weak acid or base) , particularly it the composi
tion contains suliamic acid.
‘ B-naphthoxyacetamide is substituted- for the
phenylacetamide of Example I.
I
Example‘ IV
-
4
'
'
‘
.
-
a
,,
-,
-
The following-are a few examples 01'- dry com
'
30
positions
‘
suitable v:lfor
Example‘)!
killing weeds:
'
r,
a -
1
'
Parts
'l-naphthylacetamide .......... _.| ________ -_
2
Levulinic acid ________________ ___ _____ _..'\___'_ 20
Any amide or thioamide oftheinventionm-ie
Tween #20"; ___________________________ __ '20
Aerosol
35
The. three ingredients are mixed together to
form a solution, and ?nally diluted "with _958
parts of water.
‘
e
Corp., New York), or Santomerse. (Mon? '
santo Chemical Co.,“St. Louis, Missouri)__‘_ 1
Ta1'c__'__;___'_
'
Example V
.
I'
in‘
,‘,‘98
v_
_
I
-
Parts
Talc-
Parts
2.4.5-trichlorophenoxyacetamide ____ __'____-
2 '
Carbitol '_'_ ..... _‘_ ___________ _'._-_;.__..'.__
20
Sulphonated' castor oil _____ ___ ____ __' _____ __ 100
Water ___‘ ______________________________ __‘ 878
First the amide is ‘dissolved in the carbitol
and the sulphonated castor oil, and the solution
'
.
Oil (light motor grade); ______________ _____,___ '3
v
is then mixed with the water.
r
j
Any‘amide or thioamide.oi'theinventiom-" -2
’
‘
"
"
Ea‘dmple x:
I The .levulinic acid serves not onlyas a mutual
'
~
'
solvent but also as an acidifying agent.
-i
1
(American Cy'anamid 8: ‘Chemical T" ‘
‘95
The ingredients in each of theioregoing ex
45 amples are thoroughly ground together in- a
pebble mill. The resulting compositions are in‘-v
tended to be ‘applied to the leaves? of the weeds
in the form of dusts.
I
i
.
>
The 'compositions'of the invention lend them
selves particularly to application to'w'eeds in the
'
form of ?ne mists or aerosols. If they are to be
Example VI
Bf-naphthoxy-alpha-propionamide may be sub
applied in this manner, they should be dissolved
stituted for the 2.4.5-trichlorophenoxyacetamide
drocarbons such as tetrafiuormethane, halogen
of Example V.
7
in a ‘very volatile solvent such as ?uorinated hy
'
ated hydrocarbons containing-both chlorine'and
Example VII
?uorine such as dichlorodi?uoromethane (Freon), _
or dimethyl ether.
P-chlorophenoxyacetamide may be substituted
for the phenylacetamide of Example I.
_ Example VIII
_
60
aerosols.v
4-nitro-naphthyl4l-acetamide ___________ __
2
20
_. ._
;
-v
v
.2
‘v
-
I
1. Percent
Any compound oi ,inventionv___-____;_r ______ __
Sodium lauryl sulphate ________________ __,_-.
‘5
Water _‘_ _____________________________ __'_- 873
1
Dimethyl ether___‘_‘_, _____________________ __ 90
Mutual solvent such as cyclohexanoneuqim
The amide is ?rstdissolved in the carbitol,
then mixed with the 'oil‘ and sodium lauryl
>
a.
-
Example IX
~
Example XII
Sulphonated corn oil ______ -, ___________ -_ 100
sulphate, and then with the'water.
-
Parts
Carbitol _____________________ __'-.'-___;___'_
'
The following are a few- examples of compounds
suitable for application in the form of mists or
70
l-naphthylimmoacetamide may be substituted
for the 4-nitro-naphthy1-l-acetamide of Example
»
Emample'XIII
*
v
_
‘,
7
_
9
r
-Percent,
Any compoundjof'inventionsm _____ _; ____ __
Freon
Mutual
.1
_____ __‘ ________ __1__;_H_;_‘ ____ _.v_______ 89
solvent ____ __‘____'_‘_'______ __‘ ____ __‘__ 10
The compositions-made in accordance with the
invention may beapplied for their intended’ pur
It is noted that in certain of the examples; 75
pose in severaldi?erent ways.
~
-
Y‘
--
’ ‘
‘
-8
The most advantageous and presently preferred
selected from the group consisting of the amides
way is to spray the composition on'the leaves of
the plant to be exterminated- This method takes
advantage‘ of the normal path taken by natu
rally-occurring hormones.
and thioamldes of phenyl, phenoxy, phenyimer
canto; Dhenylimlno, naphthyl, naphthoxy, naph
thylmercapto, naphthylimino, and anthracyl,
-
monocarboxylic acids. in a concentration of at
Another method is to cut of! the top of the
least .02% by weight.
stem of the plant, and then bend the stem over
5. A method for killing weeds in an active
state of growth, which‘ consists in applying to
the leaves of the weeds a composition contain
into a solution of the herbicide. The plant ab
sorbs sufficient herbicide in this manner to kill
itself.
10 ing an active ingredient, water and a water
I am not precluded from using the herbicides of
soluble, non-ionic wetting, dispersing and emul
the invention in other ways, as by applying them
sifying agent, said active ingredient being selected
to the roots.
_
>
_
'
from the group consisting of the amides and
At this point, it is to be noted that the effec
thioamides of phenyl, phenoxy. nhenylmercapto.
tiveness of a herbicide can be considerably in 15 phenylimino, naphthyl, naphthoxy, naphthyl
creased by applying it on a sunny day when the
mercapto, naphthylimino, and anthracyl, mono
temperature is over 70' F.
carboxylic aliphatic acids, and comprising at
It is also to be noted that the compositions of
least about .02% of said composition.
the invention have an accumulative effect on
6. A method for killing weeds in an active
plants, so that by spraying a plant with a com 20 state of growth, which consists in applying to the
position of half strength on two occasions, two
leaves of the weeds a composition containing a
or three weeks apart. the plant will be killed,
substance selected from the group consisting of
though the first application itself is not suf
the amides and thioamides of phenyl, phenoxy,
ncient.
phenylmercapto, phenylimino. naphthyl, naph
thoxy. naphthylmercapto, naphthylimino, and
anthracyl. monocarboxylic aliphatic acids, and
>
The compositions of this invention are much
more effective than previously-used chemicals,
comprising at least about .02% of the weight of
the composition, water and a water-soluble, non
and are capable of killing weeds, which are
noxious, insidious and persistent like poison ivy
ionic emulsifying agent containing polyether
in a period of two to three weeks. They can be
applied to large areas at relatively small expense
and have the added advantage that unlike prior
herbicides they do not render the area sterile.
Furthermore, they are not harmful to either man
or beast, and can be readily handled without any
danger.
groups of the formula R. 0. (021140) a.Ri, where
R is an alkyl, aryl, aralkyl, albl-aryl, or acyl
group of at least 10 carbon atoms, and R1 is an
alkyl, aryl, aralkyl, alkyl-aryl or acyl group or a
hydrogen atom. and n. is an integer greater
35
In conclusion, it is to be understood that the
examples have been given for illustrative pur
poses only, and that the invention is not tobe
limited thereto.
This application is a continuation-impart of 40
my prior application Serial No. 529,171 ?led April
1, 1944.
than 2.
v
7. A method for killing weeds in an active state
of growth, which consists in applying to the
leaves of the weeds a composition containing
naphthylacetamide and a wetting, dispersing and
emulsifying agent, the ‘naphthylacetamide com
prising at least about .02% of the composition.
8. A method for killing weeds in an active state
I claim:
of growth, which consists in applying to the
1. A method for killing weeds in an active
leaves of the weeds a composition containing
state of growth, which consists in applying to 45 naphthylacetamide, water and a water-soluble
the weeds a substance selected from the group
non-ionic wetting, dispersing and emulsifying
consisting of the amides and thioamides of phen
agent, the naphthylacetamide comprising at least
yl, phenoxy, phenylmercapto, phenylimino, naph
thyl,‘naphthoxy, naphthylmercapto, naphthyl
imino, and anthracyl, monocarboxylic aliphatic
50 of growth, which consists in applying to the
acids, in a concentration of at least about .05%
leaves of the weeds a composition containing
about .02% of the composition.
9. A method for. killing weeds in an active state
by weight.
2. A method for killing weeds in an active state
of growth, which consists in applying to the leaves
of the weeds a substance selected from the group 55
consisting of the amides and thioamides of phen
yl, phenoxy, phenylmercapto, phenylimino, naph
thyl, naphthoxy, naphthylmercapto, naphthyl
imino, and anthracyl, monocarboxylic aliphatic
2.4-dichlorophenoxyacetamide, and a wetting,
dispersing and emulsifying agent, the 2.4
dichlorophenoxyacetamide comprising at least
least about .02% of the composition.
10. A method for killing weeds in an active
state of growth, which consistsin applying to
the leaves of the weeds a, composition containing
2.4-dichlorophenoxyacetamide, water and a
acids, in a concentration of at least about 05% 60 water-soluble non-ionic wetting, dispersing and
by weight.
"
emulsifying agent the 2.4-clichlorophenoxyacet
3. A method for killing weeds in an active state
amide comprising at least about .02% of the
composition.
of growth, which consists in applying to the leaves
of the weeds an aqueous solution of a substance
11. A method for killing weeds in ah active
selected from the group consisting of the amides 65 state of growth, which consists in applying to
and thioamides of phenyl, phenoxy, phenylmer
capto, phenylimino, naphthyl, naphthoxy, naph
thylmercapto, naphthylimino, and anthracyl,
the leaves of the weeds a composition containing
2.4.S-trichIorophenoXyacetamide, and a wetting,
dispersing and emulsifying agent, the 2.4.5-tri
monocarboxylic aliphatic acids, in a concentra
chlorophenoxyacetamide comprising at least
tion of at least about .05% by weight.
70 about .02 of the composition.
4. A method for killing weeds in an active state
12. A method for killing weeds in an active
of growth, which consists in applying to the leaves
state of growth, which consists in applying to
of the weeds a composition containing an active
the leaves of the weeds a composition containing
ingredient, water and a wetting, dispersing and
2.4.5-trichlorophenoxyacetamide. water and a
emulsifying agent, said active ingredient being 75 water-soluble non-ionic wetting, ‘dispersing and
2,412,510
emulsifying agent, the 2.4.5-trichlorophenoxy
10
' . and emulsifying agent, the active ingredient be
acetamide comprising at least about .02% of the
ing 2.4-dichlorophenoxyacetamide, and compris
composition.
ing at least about .02% by weight of said com
13. A composition for killing weeds in an active
state of growth, said composition containing an
active ingredient, water and a wetting, dispersing
and emulsifying agent, the active ingredient being
position.
18. A composition for killing weeds in an active
state of growth, said composition containing an
active ingredient, water and a wetting, dispersing
- selected from the group consisting of the amides
and emulsifying agent, the active ingredient be
and thioamides of phenyl, phenoxy, phenylmer
capto, phenylimino, naphthyl, naphthoxy, naph
thylmercapto, naphthylimino, and anthracyl,
monocarboxylic aliphatic acids, and comprising at
ing 2.4.5-trichlorophenoxyacetamide, and com
10 prising at least about .02% by weight of said com
least about .02% by weight of said composition.
position.
19. A composition containing a substance se
lectedgrom the group consisting of the amides
and thioamides of phenyl, phenoxy, phenylmer
14. A composition for killing weeds in an active
state of growth, said composition containing an 15 capto, phenylimino, naphthyl, naphthoxy, naph
thylmercapto, naphthylimino, and anthracyl,
active ingredient, water and a water-soluble,
non-ionic wetting, dispersing and emulsifying
monocarboxylic aliphatic acids, mixed with a
agent, the active ingredient being selected from
the group consisting of the amides and thin-
amidesv of phenyl, phenoxy, phenylmercapto,
phenylimino, naphthyl,~ naphthoxy, naphthyl
wetting, dispersing and emulsifying agent, and
comprising at least one per cent of the composi
20 tion, said composition being capable of being
mercapto, naphthylimino, and anthracyl, mono
mixed with water to form a solution containing
at least .02% by weight of said substance and
carboxylic aliphatic acids, and comprising at least
about .02% by weight of said composition.
having herbicidal properties.
20. A composition containing naphthylacet
15. A composition for killing weeds in an active 25 amide mixed with a wetting, dispersing and emul
state of growth, said composition containing a
sifying agent and comprising at least one per
cent of the composition, said composition being
substance selected from the group consisting of
the amides and thioamides of phenyl, phenoxy, ‘ capable of being mixed with water to form a
phenylmercapto, ~phenylirnino, naphthyl, naph
solution containing at least .02% by weight of
thoxy, naphthylmercapto, naphthylimino, and 30 said naphthylacetamide and having herbicidal
properties.
anthracyl, inonocarboxylic aliphatic acids, and
21. A composition containing 2.4-dichloro
phenoxyacetamide mixed with a wetting, dis
ionic emulsifying agent containing polyether
persing and emulsifying agent and comprising at
groups of the formula R.O. (C2H40)n.R1, where 35 least one per cent of the composition, said compo
R is- an alkyl, aryl, aralkyl, alkyl-aryl, or acyl
sition being capable of being mixed with water
to form a solution containing at least .02%
group of at least 10 carbon atoms, and R1 is an
alkyl, aryl, aralkyl, alkyl-aryl or acyl group or a
by weight of said 2.4-dichlorophenoxyacetamide
hydrogen atom, and n is an integer greater than 2.
and having herbicidal properties.
16. A composition for killing weeds in an active 40
22. A composition containing 2.4.5-trichloro
phenoxyacetamide mixed with a wetting, dis
state of growth, said composition containing an
active ingredient, water and a wetting, dispersing
persing and emulsifying agent ‘and comprising at
and emulsifying agent, the active ingredient be
least one per cent'of the'composition, said compo
ing naphthylacetamide, and comprising at least
sition being capable of being mixed with water to
about .02% by weight of said composition.
45 form a solution containing at least 432% by weight
of said 2.4.5-trichlorophenoxyacetamide and hav
1'7. A composition for killing weeds in an active
state of growth, said composition containing an
ing herbicidal properties.
comprising at least about .02% of the weight of
i the composition, water and a water-soluble, non
active ingredient, water and a wetting, dispersing
FRANEJN 2D. JONES.
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