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Patent 2625415 Summary

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(12) Patent: (11) CA 2625415
(54) English Title: ENHANCERS FOR WATER SOLUBLE SELECTIVE AUXIN TYPE HERBICIDES
(54) French Title: AGENTS AMPLIFICATEURS POUR HERBICIDES SELECTIFS HYDROSOLUBLES DU TYPE AUXINE
Status: Deemed expired
Bibliographic Data
(51) International Patent Classification (IPC):
  • A01N 37/44 (2006.01)
  • A01N 37/40 (2006.01)
  • A01N 39/04 (2006.01)
  • A01N 43/40 (2006.01)
  • A01N 43/42 (2006.01)
  • A01P 13/02 (2006.01)
(72) Inventors :
  • DIEBOLD, R. SHANE (Canada)
  • MORGAN, KIM F. (Canada)
  • WILSON, CAMERON D. (Canada)
(73) Owners :
  • W. NEUDORFF GMBH KG (Germany)
(71) Applicants :
  • W. NEUDORFF GMBH KG (Germany)
(74) Agent: AIRD & MCBURNEY LP
(74) Associate agent:
(45) Issued: 2015-05-05
(22) Filed Date: 2008-03-12
(41) Open to Public Inspection: 2008-09-14
Examination requested: 2013-01-07
Availability of licence: N/A
(25) Language of filing: English

Patent Cooperation Treaty (PCT): No

(30) Application Priority Data:
Application No. Country/Territory Date
11/686,098 United States of America 2007-03-14

Abstracts

English Abstract


A selective herbicide, as well of methods of controlling unwanted plants using

such a herbicide, are provided. A method for treating undesired vegetation can

include providing a selective herbicidal composition that includes a water-
soluble
selective auxin-type herbicide and a chelating agent complexed with at least
one
transition metal, and contacting vegetation with a herbicidally effective
amount of the
composition such that unwanted vegetation is controlled, while desired
vegetation is
unaffected.


French Abstract

On propose un herbicide sélectif ainsi que des procédés de lutte contre les plantes indésirables à laide dun tel herbicide. Un procédé pour le traitement dune végétation indésirable peut consister à utiliser une composition herbicide sélective qui comprend un herbicide sélectif de type auxine soluble dans leau et un agent chélatant complexé avec au moins un métal de transition, et à mettre en contact la végétation avec une quantité efficace sur le plan herbicide de la composition de sorte que la végétation indésirable est maîtrisée, alors que la végétation désirable nest pas touchée.

Claims

Note: Claims are shown in the official language in which they were submitted.


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We claim:
1. A method for controlling undesired vegetation susceptible to selective
auxin-type
herbicides, comprising the steps of:
providing a selective herbicidal composition comprising a water-soluble
selective
auxin-type herbicide selected from the group consisting of a phenoxyacetic
acid, a
phenoxyalkanoic acid, a benzoic acid and mixtures thereof, and a chelating
agent complexed
with at least one transition metal; and
contacting vegetation with a herbicidally effective amount of the composition
such
that the undesired vegetation is controlled, while desired vegetation is
unaffected.
2. The method of claim 1, wherein the water-soluble selective auxin-type
herbicide is
selected from the group consisting of (2,4-dichlorophenoxy)acetic acid, 3,6-
dichloro-2-
methoxybenzoic acid, (~)-2-(2,4-dichlorophenoxy)propanoic acid, (4-chloro-2-
methylphenoxy)acetic acid, (~)-2-(4-chloro-2- methylphenoxy)propanoic acid,
and
combinations thereof.
3. The method of claim 2, wherein the water-soluble selective auxin-type
herbicide is
in the form of an acid, an ester, a salt, or combination thereof.
4. The method of claim 1, wherein the water-soluble selective auxin-type
herbicide is
present within the composition at a concentration in a range of 0.00001 to 20%
by weight
when the composition is applied to the vegetation.
5. The method of claim 1, wherein the transition metal is selected from the
group
consisting of copper, iron, manganese, zinc, and combinations thereof.
6. The method of claim 5, wherein the transition metal is iron.
7. The method of claim 1, wherein the transition metal is present in the
composition at
a concentration in a range of 0.01 to 5% by weight when the composition is
applied to the
vegetation.

- 22 -
8. The method of claim 1, wherein the chelating agent is selected from the
group
consisting of an aminopolycarboxylate, an amino acid, a salicylate, and
combinations
thereof.
9. The method of claim 8, wherein the aminopolycarboxylate is selected from
the
group consisting of ethylenediaminedisuccinic acid, ethylenediaminetetraacetic
acid,
ethanoldiglycine, hydroxyethylenediaminetriacetic acid, methylglycinediacetic
acid,
glutamicaciddiacetic acid, trans-1,2-diaminocyclohexane-N,N,N',N'tetraacetic
acid,
diethylenetriaminepentaacetic acid, iminodisuccinic acid, their salts, and
combinations
thereof
10. The method of claim 1, wherein the chelating agent is present within
the
composition at a concentration in a range of 0.1 to 25% by weight when the
composition is
applied to the vegetation.
11. The method of claim 1, further comprising an additional component
selected from
the group consisting of growth regulators, fertilizers, other selective
herbicides, thickening
agents, humectants, antioxidants, surfactants, stabilizing agents, wetting
agents, herbicide
synergists, sequestrants, solvents, dyes, and combinations thereof
12. A method of controlling undesired vegetation susceptible to selective
auxin-type
herbicides, comprising:
providing a herbicidal composition comprising a water-soluble selective auxin-
type
herbicide selected from the group consisting of a phenoxyacetic acid, a
phenoxyalkanoic
acid, a benzoic acid and mixtures thereof, and an ethylenediaminedisuccinic
compound; and
contacting vegetation with a herbicidally effective amount of the composition
such
that the undesired vegetation is selectively controlled, while desired
vegetation is undamaged.
13. The method of claim 12, wherein the ethylenediaminedisuccinic compound
is in the
form of an acid or a salt.

- 23 -
14. The method of claim 13, wherein the ethylenediaminedisuccinic salt is
selected from
the group consisting of sodium salts, potassium salts, ammonium salts, and
combinations
thereof.
15. The method of claim 14, wherein a sodium ion, potassium ion or ammonium
ion
component of the ethylenediaminedisuccinic salt is present within the
composition in a range
of 0.01 to 5% by weight when the composition is applied to the vegetation.
16. The method of claim 13, wherein the ethylenediaminedisuccinic compound
of the
ethylenediaminedisuccinic salt is present within the composition at a
concentration in a range
of 0.1 to 25% by weight when the composition is applied to the vegetation.
17. The method of claim 12, further comprising an additional component
selected from
the group consisting of growth regulators, fertilizers, other selective
herbicides, thickening
agents, humectants, antioxidants, surfactants, stabilizing agents, wetting
agents, herbicide
synergists, sequestrants, solvents, dyes and combinations thereof.
18. A method for controlling undesired vegetation susceptible to selective
auxin-type
herbicides, comprising the steps of:
providing a selective herbicidal composition comprising a water-soluble
selective
auxin-type herbicide selected from the group consisting of a phenoxyacetic
acid, a
phenoxyalkanoic acid, a benzoic acid and mixtures thereof, a chelating agent
and a metal
salt; and
contacting vegetation with a herbicidally effective amount of the composition
such
that the undesired vegetation is controlled, while desired vegetation is
unaffected.
19. The method of claim 18, wherein a metal component of the metal salt is
a transition
metal.
20. The method of claim 1, wherein the vegetation susceptible to selective
auxin-type
herbicides comprises broadleaf weeds in grass or turf.

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21. The method of claim 12, wherein the vegetation susceptible to selective
auxin-type
herbicides comprises broadleaf weeds in grass or turf.
22. The method of claim 18, wherein the vegetation susceptible to selective
auxin-type
herbicides comprises broadleaf weeds in grass or turf.

Description

Note: Descriptions are shown in the official language in which they were submitted.


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ENHANCERS FOR WATER SOLUBLE SELECTIVE AUXIN TYPE HERBICIDES
10
FIELD OF THE INVENTION
The present invention relates to water-soluble selective auxin-type herbicides
and
methods for controlling unwanted vegetation.
BACKGROUND OF THE INVENTION
The control of unwanted vegetation is a continually important effort as it is
needed for reducing health problems, such as allergies, the removal of
poisonous/noxious weeds, increasing crop productivity, as well as improving
the general
aesthetics around the home. Unwanted vegetation can be controlled using
herbicides
that are either selective or non-selective. An example of a commonly used non-
selective
herbicide is glyphosate, marketed under the trade name Roundup , among others,
which
kills all vegetation it contacts. Alternatively, a selective herbicide only
affects the
undesired plant species while leaving the desired species relatively
unaffected. An
example of a well-known auxin-type selective herbicide is 2,4-
dichlorophenoxyacetic
acid (also known as "2,4-D"), which is commonly used for the removal of
broadleaf
weeds growing in grass and turf.
There are a variety of selective herbicides that are available on the market
for the
selective control of grass and broadleaf weeds growing in a variety of crops.
The
majority of these herbicides are synthetic compounds, with some herbicides
raising
concerns in recent years as to their safety to humans and the environment in
general.
Within the context of postemergent broadleaf weed control in grass, auxin-type

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herbicides are commonly used. There are four main families of synthetic auxin-
type
herbicides available on the market, including: the phenoxyacetic acid or
phenoxyalkanoic acid family (e.g. 2,4-D), the benzoic acid family (e.g.
dicamba), the
pyridine carboxylic acid or picolinic acid family (e.g. triclopyr), and the
quinolinecarboxylic acid family (e.g. quinclorac). These auxin-type herbicides
are
systemic compounds that have activity against a number of broadleaf weeds
including
perennial species. A number of registered products exist with these compounds,
some
using the individual compounds alone while others have two or three combined
together
io (e.g., Killex contains 2,4-D, mecoprop and dicamba).
A drawback of the synthetic auxin-type herbicides is their slow speed of
activity.
Often herbicidal activity is not seen for several weeks after application.
Moreover, the
products that are available for use by homeowners often do not result in
adequate weed
control with one application, resulting in the need for additional
applications in order to
achieve acceptable weed control.
Accordingly, there is a need in the art for novel methods and compositions for

the improvement and enhancement of selective auxin-type herbicides that will
benefit
both consumers and the environment.
SUMMARY OF THE INVENTION
The present invention is generally directed to methods and compositions for an

enhanced water-soluble selective herbicide. In particular, the present
invention provides
an enhanced and/or synergistic, effective, fast-acting, long-lasting water-
soluble
selective herbicide that will remove unwanted broadleaf weeds from grass and
turf. In
one embodiment, an exemplary method for treating undesired vegetation can
include
providing a selective herbicidal composition that includes a water-soluble
selective
auxin-type herbicide and a chelating agent complexed with at least one
transition metal,
and contacting vegetation with a herbicidally effective amount of the
composition such
that unwanted vegetation is controlled, while desired vegetation is
unaffected.
In one aspect, the exemplary method can provide a selective herbicidal
composition that includes a water-soluble selective auxin-type herbicide in
the form of
an acid, an ester, a salt, and combinations thereof. The metal component of
the
composition can be a transition metal selected from the group consisting of
copper, iron,

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manganese, zinc, and combinations thereof. The chelating agent component of
the
composition can be a chelating agent selected from the group consisting of an
aminopolycarbonoxylate, an amino acid, a salicyalate, and combinations thereof
In another embodiment, an exemplary method for treating undesired
vegetation involves providing a herbicidal composition that can include a
water-
soluble selective auxin-type herbicide and an ethylenediaminedisuccinic
compound,
and contacting vegetation with a herbicidally effective amount of the
composition
such that unwanted vegetation is selectively controlled, while desired
vegetation is
undamaged.
In one aspect, the exemplary method can provide a herbicidal composition
wherein a ethylenediaminedisuccinic compound is in the form of an acid or a
salt.
When the ethylenediaminedisuccinic compound is a salt, it is selected from the
group
consisting of sodium salts, potassium salts, ammonium salts, and combinations
thereof.
In yet a further aspect the present invention resides in a method for
controlling
undesired vegetation susceptible to selective auxin-type herbicides,
comprising the
steps of: providing a selective herbicidal composition comprising a water-
soluble
selective auxin-type herbicide selected from the group consisting of
phenoxyacetic
acid, phenoxyalkanoic acid, benzoic acid and mixtures thereof, and a chelating
agent
complexed with at least one transition metal; and contacting vegetation with a

herbicidally effective amount of the composition such that the undesired
vegetation
is controlled, while desired vegetation is unaffected.
In a further aspect the present invention resides in a method of controlling
undesired vegetation susceptible to selective auxin-type herbicides,
comprising:
providing a herbicidal composition comprising a water-soluble selective auxin-
type
herbicide selected from the group consisting of phenoxyacetic acid,
phenoxyalkanoic
acid, benzoic acid and mixtures thereof, and an ethylenediaminedisuccinic
compound;
and contacting vegetation with a herbicidally effective amount of the
composition
such that the undesired vegetation is selectively controlled, while desired
vegetation is
undamaged.

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DETAILED DESCRIPTION OF THE INVENTION
Certain exemplary embodiments will now be described to provide an overall
understanding of the principles of the structure, function, manufacture, and
use of the
devices and methods disclosed herein. Those skilled in the art will understand
that
the devices and methods specifically described herein are non-limiting
exemplary
embodiments and that the scope of the present invention is defined solely by
the
claims. The features described in connection with one exemplary embodiment may

be combined with the features of other embodiments. Such modifications and
variations are intended to be included within the scope of the present
invention.
The present invention provides a more environmentally compatible selective
herbicide that is effective to remove unwanted broadleaf weeds while leaving
grasses
and other desirable plants unaffected. The composition comprises a water-
soluble
auxin-type herbicide and a chelating agent that is complexed with at least one

transition metal. The composition is useful in a method of treating undesired
vegetation in which the composition is provided and vegetation is contacted
with a
herbicidally effective amount of the composition such that unwanted vegetation
is
controlled, while desired vegetation is unaffected. The sources of the
chelating agent
and the transition metal that

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form the complex can vary, as described below. In another embodiment, the
composition used to selectively kill unwanted vegetation is an environmentally

compatible selective herbicide composition comprising the combination of a
water-
s soluble selective auxin-type herbicide and an ethylenediaminedisuccinic
compound.
One characteristic of the compositions and the methods disclosed herein is the
enhanced
and/or synergistic activity that is achieved when the composition is applied
to vegetation
to control undesired vegetation.
In one aspect, the metal component used to form the complex of the present
invention includes a transition metal. Suitable transition metal ions include,
for
example, copper ions, iron ions, manganese ions, zinc ions, and combinations
thereof.
In an exemplary embodiment, the metal component includes an iron ion, which
can be
present in a variety of ionic states. By way of non-limiting example, iron
ions used in
the present invention can be added as Fe+2 ions, Fe+3 ions, and mixtures
thereof.
The metal component of the present invention can be added in a variety of
forms.
In one embodiment, the metal ions can be added as a metal salt. Exemplary
metal salts
include metal chlorides, metal sulfates, metal nitrates, metal citrates, metal
phosphates,
metal sulfides, metal sulfites, metal succinates, metal gluconates, metal
lactates, metal
formates, metal nitrites, metal salicylates, metal carboxylic acids, and
combinations
thereof.
Another component of the herbicidal composition that forms a complex with a
transition metal is a chelating agent. A variety of chelating agents can be
used in the
water-soluble selective auxin-type herbicide compositions of the present
invention to
form a metal chelate. By way of non-limiting example, suitable chelating
agents include
aconitic acid, alanine diacetic acid (ADA), alkoyl ethylene diamine triacetic
acids (e.g.,
lauroyl ethylene diamine triacetic acids (LED3A)), aminotri
(methylenephosphonic acid)
(ATMP), asparticaciddiacetic acid (ASDA), asparticacidmonoacetic acid, diamino
cyclohexane tetraacetic acid (CDTA), citraconic acid, citric acid, 1,2-
.=
diaminopropanetetraacetic acid (DPTA-OH), 1,3-diamino-2-propanoltetraacetic
acid
(DTPA), diethanolamine, diethanol glycine (DEG), diethylenetriaminepentaacetic
acid
(DTPA), diethylene triamine pentamethylene phosphonic acid (DTPMP), diglycolic

acid, dipicolinic acid (DPA), ethanolaminediacetic acid, ethanoldiglycine
(EDG),
ethionine, ethylenediamine (EDA), ethylenediaminediglutaric acid (EDDG),

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ethylenediaminedi(hydroxyphenylacetic acid (EDDHA), ethylenediaminedipropionic

acid (EDDP), ethylenediaminedisuccinate (EDDS), ethylenediaminemonosuccinic
acid
(EDMS), ethylenediaminetetraacetic acid (EDTA), ethylenediaminetetrapropionic
acid
(EDIT), ethyleneglycolaminoethylestertetraacetic acid (EGTA), gallic acid,
glucoheptonic acid, gluconic acid, glutamicaciddiacetic acid (GLDA), glutaric
acid,
glyceryliminodiacetic acid, glycinamidedisuccinic acid (GADS),
glycoletherdiaminetetraacetic acid (GEDTA), 2-hydroxyethyldiacetic acid,
hydroxyethylenediaminetriacetic acid (HEDTA), hydroxyethyldiphosphonic acid
(HEDP), 2-hydroxyethyl imino diacetic acid (HIMDA), hydroxyiminodiacetic acid
(HIDA), 2-hydroxy propylene diamine disuccinic acid (HPDDS), iminodiacetic
acid
(IDA), iminodisuccinic acid (IDS), itaconic acid, lauroyl ethylene diamine
triacetic acids
(LED3A), malic acid, malonic acid, methylglycinediacetate (MGDA),
methyliminodiacetic acid (MIDA), monoethanolamine, nitrilotripropionic acid
(NPA),
N-phosphonomethyl glycine (glyphosate), propyldiamine tetraacetic acid (PDTA),
salicylic acid, serinediacetic acid (SDA), sorbic acid, succinic acid, sugars,
tartaric acid,
tartronic acid, triethanolamine, triethylenetetraamine, triethylene tetraamine
hexaacetic
acid (TTHA), and combinations thereof. In an exemplary embodiment, the
chelating
agent is HEDTA, EDTA, CDTA, EDDS, GLDA MGDA, IDS, EDG, DTPA, isomers
thereof, and combinations thereof.
Other suitable chelating agents that can be used in the herbicidal
compositions of
the present invention to form the metal chelate include citric acid, salicylic
acid and salts
thereof, such as ammonium salicylate, and combinations thereof. Amino acids
can also
be used as chelating agents in the present invention. Suitable amino acids
include
alanine, arginine, asparagine, aspartic acid, glutamic acid, glutamine,
glycine, histidine,
isoleucine, leucine, lysine, methionine, proline, serine, threonine, tyrosine,
valine, and
combinations thereof
The chelating agent can be present in the herbicidal composition in a variety
of
forms, alone or in combination. In one embodiment, the chelating agent can be
in the
form of a free acid. In another embodiment the chelating agent can be a salt.
Exemplary
salt forms of the chelating agent include sodium salts, potassium salts,
calcium salts,
ammonium salts, amine salts, amide salts, magnesium salts, and combinations
thereof
The actual compounds that can be used to form this component of the herbicidal

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composition include those chelating agents described above.
Suitable water-soluble selective auxin-type herbicides for use with this
invention
include aminopyralid (4-amino-3,6-dichloropyridine-2-carboxylic acid),
clomeprop
((RS)-2-(2,4-dichloro-m-tolyloxy)propionanilide), clopyralid (3,6-dichloro-2-
pyridinecarboxylic acid), 2,4-D ((2,4-dichlorophenoxy)acetic acid), dicamba
(3,6-
dichloro-2-methoxybenzoic acid), dichlorprop (( )-2-(2,4-
dichlorophenoxy)propanoic
acid), fluroxypyr ([(4-amino-3,5-dichloro-6-fluoro-2-pyridinyl)oxy]acetic
acid), MCPA
((4-chloro-2-methylphenoxy)acetic acid), mecoprop (( )-2-(4-chloro-2-
methylphenoxy)propanoic acid), picloram (4-amino-3,5,6-trichloro-2-
pyridinecarboxylic
acid), quinclorac (3,7-dichloro-8-quinolinecarboxylic acid), quinmerac (7-
chloro-3-
methy1-8-quinolinecarboxylic acid), triclopyr ([(3,5,6-trichloro-2-
pyridinyl)oxy]acetic
acid), their salts, acids, esters, and combinations thereof
Some of the water-soluble selective auxin-type herbicide components of the
present invention can also be added in a variety of forms. In one embodiment,
the
auxin-type herbicide can be added as a salt, and exemplary salts include
potassium salts,
sodium salts, ammonium salts, isopropylamine salts, dimethylamine salts,
triethylamine
salts, diglycolamine salts, triisopropanolamine salts, triisopropanolammonium
salts,
monoethanolamine salts, diethanolamine salts, and combinations thereof. In
another
embodiment, the herbicide can be added as an acid. In yet another embodiment,
the
herbicide can be added as an ester such as a butoxyethyl ester, ethylhexyl
ester, isooctyl
ester, methylheptyl ester, and combinations thereof.
Where the herbicide composition includes a metal salt, a chelating agent, and
a
water-soluble selective auxin-type herbicide, the concentration of the metal
ion, the
chelating agent and the herbicide can vary significantly. By way of non-
limiting
example, the concentration of metal ions applied to the plant should be in the
range of
about 0.01 to 5% by weight, and more preferably in the range of about 0.05 to
2% by
weight; the concentration of the chelating agent applied to the plant can be
in the range
of about 0.1 to 25% by weight, and more preferably in the range of about 0.2
to 10% by
weight, the concentration of the water-soluble selective auxin-type herbicide
applied to
the plant can be in the range of about 0.00001 to 20% by weight, and more
preferably in
the range of about 0.00005 to 15% by weight.

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In another aspect, the composition comprises a water-soluble selective auxin-
type herbicide and an ethylenediaminedisuccinic compound. The
ethylenediaminedisuccinic compound can be in the form of an acid or a salt.
Exemplary
salt forms of this compound include sodium salts, potassium salts, ammonium
salts, and
combinations thereof. In this embodiment, the sodium, potassium or ammonium
ions
can be present in the composition at a concentration in the range of about
0.01 to 5% by
weight, and more preferably at a concentration in the range of about 0.05 to
2% by
weight, while the ethylenediaminedisuccinic compound can be present in the
composition at a concentration in the range of about 0.1 to 25% by weight, and
more
preferably at a concentration in the range of about 0.2 to 10 % by weight,
when the
composition is applied to vegetation. The concentration of the water-soluble
selective
auxin-type herbicide applied to the plant can be in the range of about 0.00001
to 20% by
weight, and more preferably at a concentration in the range of about 0.00005
to 15% by
weight.
Besides the ingredients described above, a variety of other components can be
added to the herbicide compositions. By way of non-limiting example, these
additives
can include fertilizers, growth regulators, selective herbicides, thickening
agents, dyes,
and combinations thereof.
A variety of fertilizers may be added to the herbicidal composition of the
present
invention. The end-use concentration of added fertilizer(s) can vary, but
preferably, the
concentration of fertilizer is in the range of about 0.1 to 5% by weight.
A variety of growth regulators may also be added to the herbicidal composition

of the present invention. By way of non-limiting example, the growth
regulators added
to the herbicidal compositions can include maleic hydrazide (MH), cycocel (2-
chloroethyl-trimethyl ammonium chloride), and combinations thereof. The end-
use
concentration of the additional growth regulators can vary, but preferably,
the
concentration is between about 0.01 and 2% by weight.
The herbicidal compositions of the present invention can also include natural
growth regulators, such as ammonium salicylate, jasmonates, ethylene, auxins,
gibberellins, cytokinins, abscisic acid, and combinations thereof. The end-use

concentration of these natural growth regulators can vary, but preferably, the

concentration is in the range of about 0.001 to 5% by weight.

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Furthermore, a variety of thickening agents may be added to the herbicidal
compositions disclosed herein. Exemplary thickening agents include Rhodopol 23

(Rhodia), VanGel B (R. T. Vanderbilt), Kelzan S (C.P. Kelco), guar gum,
propylene
glycol, glycerol, and combinations thereof. The end-use concentration of added
thickening agent(s) can vary, but preferably, the concentration is in the
range of about
0.01 to 1% by weight.
Other additives may be included in the herbicidal compositions disclosed
herein
as well. By way of non-limiting example, such other additives can include
humectants,
antioxidants, stabilizing agents, wetting agents, surfactants, herbicide
synergists,
solvents, sequestrants, and combinations thereof. Suitable humectants include,
for
example, propylene glycol, glycerin, beet molasses, and combinations thereof.
Suitable
antioxidants include, for example, citric acid, while suitable stabilizing
agents include
citric acid, ammonium salts, and combinations thereof Suitable wetting agents
include,
for example, carboxylic acids and the salts thereof and silicone polymers such
as Silwe?
77 (G.E. Co. Advanced Materials Silicones). The end-use concentration of these

additives may vary, but preferably, the concentration is in the range of about
0.01 to 5%
by weight.
In use, the formulation of the water-soluble selective auxin-type herbicide of
the
present invention can vary. Preferably, the herbicidal compositions are formed
as a
ready-to-use composition, a liquid concentrate, a tank-mix, or a dry
concentrate. The
solvents used in the ready-to-use liquid composition and liquid concentrate
forms can
also vary and exemplary solvents include propylene glycol, glycerin, alcohols
such as
tetrahydrofurfuryl alcohol (THFA), and combinations thereof
The pH of the herbicidal solution can vary, but the herbicidal compositions of
the
present invention are effective over a wide range of pH values. An exemplary
pH is in
the range of about 1.5 to 10. After the formulation has been prepared, the pH
of the
solution can be measured and adjusted as necessary. The pH values can be
measured
using standard pH meters, with glass bulb electrodes.
An exemplary ready-to-use (RTU) formulation according to one embodiment of
the present invention includes FeHEDTA metal chelate with 0.4% iron and 0.6%
The ingredients used to form this composition are as follows:

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Concentration by weight
Ingredient
(,6)
Deionized water 95.4%
Na3HEDTA 2.8%
FeC13 1.2%
Killexe* 0.6%
* Killex contains 2,4-D (9.5%), mecoprop (5%) and dicamba (0.9%).
The RTU formulation shown above is prepared by adding deionized water to a
vessel, and adding ferric chloride to the water while stirring. Once
dissolved, the
Na3HEDTA is added, followed by additional stirring to dissolve the Na3HEDTA.
The
pH is then adjusted to between 6 and 8. Lastly, Killex is added, followed by
additional
stirring until thoroughly mixed. This solution can then be sprayed onto areas
of lawn
and weeds using a handheld trigger sprayer, a pump-wand sprayer, or broadcast
sprayer,
at a rate of about 200 ml/m2.
The herbicide compositions of the present invention can be applied to a
variety
o of undesired vegetation in both residential and commercial plant or crop
areas.
Preferably, the herbicide compositions are effective to selectively control
broadleaf
weeds growing in grass and turf areas. The herbicidal compositions disclosed
herein are
very effective against numerous common broadleaf weeds, mosses, liverworts,
and
algae. Grass and turf areas that are infested with undesired vegetation can be
entirely
sprayed with a herbicidal composition of the present invention to selectively
remove the
unwanted vegetation, while leaving the grass, turf and other desired plants
undamaged.
One advantageous characteristic of the herbicidal compositions of the present
invention is their relatively fast-acting nature. The herbicidal compositions
described in
this invention show signs of herbicidal activity within days compared to the
weeks
typically required for known auxin-type herbicides to achieve the same level
of activity.
In addition, an enhanced and/or synergistic level of herbicidal activity is
obtained
against the unwanted vegetation with the herbicidal compositions of the
current
invention, relative to the individual components if used alone. This
improvement in
herbicidal activity can be seen within days of treatment, lasting up to many
weeks after

CA 02625415 2008-03-12
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- 10 -
treatment. Furthermore, the improved weed activity that results from the
herbicide
compositions of the current invention also allows for a reduction in the
amount of the
auxin-type herbicide that is required to achieve comparable weed control to
the full rate
of the auxin-type herbicide on its own. Reducing auxin-type herbicide rates
while
maintaining similar weed control is beneficial for consumers and the
environment in
general, particularly since some of these auxin-type herbicides have raised
health
concerns in recent years. Although increased broadleaf weed activity results
with the
herbicide compositions of the present invention, selectivity is maintained
wherein
o treated grass species remain relatively unaffected, sometimes with less
injury seen than
when the individual components are applied on their own.
The following non-limiting examples serve to further describe the invention.
For
the greenhouse tests, plants were grown in a commercial greenhouse mix, using
supplemental lighting and heating. Plants were fertilized with an all purpose
water-
soluble fertilizer mix of 20-20-20 (N-P-K; Plant-Prod ) as needed. All
broadleaf weeds
were grown individually in a 21/4-inch pot until they were a suitable size for
herbicide
tests (actual weed size is reported in examples below). Perennial ryegrass was
also
grown in 21/4-inch pots, however many grass seeds were sown in the pot to
simulate a
small section of turf. Grass plants were continually trimmed to a height of 4
cm,
simulating that of a homeowner's lawn. For field tests, plots 1/4 m2 in size
were marked
out in areas containing the targeted broadleaf weed species growing in turf
grass. Plots
were continually mowed to simulate a homeowner's lawn. All of the tested
herbicidal
solutions were sprayed onto the plants at a rate of 200 ml/m2. In all of the
examples, the
amounts of the various herbicide components are identified as a percent on a
weight
basis.
Killex (Scotts Canada, Ltd., Ontario, Canada) is a commonly used selective
lawn herbicide and was used as the commercial herbicide for herbicide
combinations.
The labeled dilution and application rates for Killex are 6 ml into 1 L of
solution
(0.6%) applied at 200 ml/m2.
All visual plant damage assessments were made using a quantitative rating
scale;
percent control relative to the untreated check (0 = no effect; 100 = plant
death).

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EXAMPLE 1
Objective: To evaluate the combination of various iron chelates with Killee
for
herbicidal activity and grass injury.
Materials and Methods: This trial was conducted in the greenhouse. Nine pots
of white clover and 10 pots of perennial ryegrass were selected for each
treatment.
Herbicidal solutions were prepared using deionized water. The treatments were
applied
using a handheld trigger sprayer at 200 ml/m2. All treatments were applied
once.
Phytotoxicity (%) was assessed 4, 7, and 14 days after application (A4, A7,
and A14).
Table 1. Plant stages at the commencement of this study.
White clover Perennial tyegrass
Leaf # 20+
Plant Height (cm) 17-20 4
Growth Stage flower vegetative
Table 2. Phytotoxicity (%) against white clover,
White Clover Phytotoxiciiy (%)
A4 A7 Al4
Control 0 0 0
FeMGDA 0.4% Fe 4 5 2
FeIDS 0.4% Fe 7 10 13
FeEDTA 0.4% Fe 15 15 6
FeHEDTA 0.4% Fe 22 19 15
Killee 0.6% 10 11 28
FeMGDA 0.4% Fe + Killee 0.6% 18 20 38
FeIDS 0.4% Fe + Killee0.6% 36 37 53
FeEDTA 0.4% Fe + Killee0.6% 27 37 39
FeHEDTA 0.4% Fe + Kil1ee0.6% 57 66 66

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Table 3. Phytotoxicity (%) against perennial ryegrass.
Perennial ryegrass Phytotoxcily (%)
A4 A7 A 1 4
Control 0 0 0
FeMGDA 0.4% Fe 0 0 0
FeIDS 0.4% Fe 6 5 0
FeEDTA 0.4% Fe 4 2 0
FeHEDTA 0.4% Fe 8 7 1
Killexo 0.6% 1 1 0
FeMGDA 0.4% Fe + Killexe0.6% 7 5 0
FeIDS 0.4% Fe + Killexe0.6% 7 5 1
FeEDTA 0.4% Fe + Killexe 0.6% 4 2 0
FeHEDTA 0.4% Fe + Killexe 0.6% 5 4 3
EXAMPLE 2
Objective: To evaluate the combination of FeHEDTA metal chelates with
Killexe' for herbicidal activity and grass injury.
Materials and Methods: This trial was conducted in the greenhouse. Nine pots
of white clover and 10 pots of perennial ryegrass were selected for each
treatment.
Herbicide solutions were prepared using deionized water. The treatments were
applied
io using a hand-trigger sprayer at 200 ml/m2. All treatments were applied
once.
Phytotoxicity (%) was assessed 4, 7, and 14 days after application (A4, A7,
and A14).
Table 4. Plant stages at the commencement of this study.
White clover Perennial ryegrass
Leaf # 20+
Plant Height (cm) 15-19 4
Growth Stage vegetative vegetative

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Table 5. Phytotoxicity (%) against white clover.
White Clover Phytotoxicity (%)
A4 A7 Al4
Control 0 0 0
FeHEDTA 0.4% Fe 27 50 18
Killex 0.6% 11 12 28
FeHEDTA 0.4% Fe + Killex 0.6% 58 71 73
Table 6. Phytotoxicity (%) on perennial ryegrass.
Perennial ryegrass Phytotoxicity (%)
A4 A7 Al4
Control 0 0 0
FeHEDTA 0.4% Fe 2 1 2
Killex 0.6% 0 0 0
FeHEDTA 0.4% Fe + Killex 0.6% 1 1 1
EXAMPLE 3
Objective: To evaluate the combination of FeHEDTA metal chelate with
Killex at reduced rates.
Materials and Methods: This trial was conducted in the greenhouse. Ten
broadleaf plantain plants and 5 pots of perennial ryegrass were selected for
each
treatment. Herbicide solutions were prepared using deionized water. The
treatments
were applied using a hand-trigger sprayer at 200 ml/m2. All treatments were
applied
once. Phytotoxicity (%) was assessed 7 days after application (A7).
Table 7. Plant stages at the commencement of this study.
Broadleaf plantain Perennial ryegrass
Leaf # 4-7
Plant Diameter (cm) 25-45 3-5 (height)
Growth Stage vegetative vegetative

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- 14 -
Table 8. Phytotoxicity (%) against broadleafplantain.
Broadleaf plantain A7 Phytotoxicity (%)
Killexe 0% Killex 0.15% Killexe 0.3% Killexe 0.6%
FeHEDTA 0% Fe 0 14 23 24
FeHEDTA 0.1% Fe 9 25 29 36
FeHEDTA 0.2% Fe 10 27 30 43
FeHEDTA 0.4% Fe 22 35 42 53
Table 9. Phytotoxicity (%) against perennial ryegrass.
Perennial ryegrass A 7 Phytotoxicity (%)
Killexe 0% Killexe 0.15% Killexe 0.3% Killex 0.6%
FeHEDTA 0% Fe 0 1 1 1
FeHEDTA 0.1% Fe 1 1 3 2
FeHEDTA 0.2% Fe 1 1 2 1
FeHEDTA 0.4% Fe 2 1 1 1
EXAMPLE 4
Objective: To evaluate the combination of NH4-, Na-, K- and Fe-EDDS with
Killex for herbicidal activity and grass injury.
Materials and Methods: This trial was conducted in the greenhouse. Ten
broadleaf plantain plants and 10 pots of perennial ryegrass were selected
for each
treatment. Herbicide solutions were prepared using deionized water. The
treatments
were applied using a hand-trigger sprayer at 200 ml/m2. All treatments were
applied
once. Phytotoxicity (%) was assessed 21 days after application (A21).
Table 10. Plant stages at the commencement of this study.
Broadleaf plantain Perennial ryegrass
Leaf # 12-18
Plant Diameter (cm) 40-50 4-5 (height)
Growth Stage flower vegetative

CA 02625415 2008-03-12
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- 15 -
Table 11. Phytotoxicio) (%) against broadleaf plantain.
Broadleaf plantain Phytotoxicity (%)
A21
Control 0
NH4EDDS 2.09% a.e.a 0
NaEDDS 2.09% a.e. 6
KEDDS 2.09% a.e. 6
FeEDDS 0.4% Fe 2
Killex 0.6% 29
NH4EDDS 2.09% a.e. + Killex 0.6% 43
NaEDDS 2.09% a.e. + Killex 0.6% 59
KEDDS 2.09% a.e. + Killex 0.6% 54
FeEDDS 0.4% Fe + Killex 0.6% 47
a abbreviation a.e. = acid equivalent
Table 12. Phytotoxicity (%) on LOLPE.
LOLPE Phytotoxicity (%)
A21
Control 0
NH4EDDS 2.09% a.e.a 0
NaEDDS 2.09% a.e. 0
KEDDS 2.09% a.e. 0
FeEDDS 0.4% Fe 0
Killex 0.6% 0
NH4EDDS 2.09% a.e. + Killex 0.6% 0
NaEDDS 2.09% a.e. + Killex 0.6% 0
KEDDS 2.09% a.e. + Killex 0.6% 0
FeEDDS 0.4% Fe + Killex 0.6% 0
a abbreviation a.e. = acid equivalent

CA 02625415 2008-03-12

22698-97
- 16 -
EXAMPLE 5
Objective: To evaluate the combination of various Fe chelates with Killex for

herbicidal activity and grass injury.
Materials and Methods: This trial was conducted in the greenhouse. Seven
dandelion plants and 10 pots of perennial ryegrass were selected for each
treatment.
Herbicide solutions were prepared using deionized water. The treatments were
applied
using a hand-trigger sprayer at 200 ml/m2. All treatments were applied once.
Phytotoxicity (%) was assessed 29 days after treatment (A29).
Table 13. Plant stages at the commencement of this study.
Dandelion Perennial ryegrass
Leaf # 15-34
Plant Diameter (cm) 25-30 3-4 (height)
Growth Stage flower vegetative
Table 14. Phytotoxicity (%) against dandelion.
Dandelion Phytotoxicity (%)
A29
Control 0
FeMGDA 0.4% Fe 12
FeIDS 0.4% Fe 28
FeHEDTA 0.4% Fe 24
Killex 0.6% 54
FeMGDA 0.4% Fe + Killex 0.6% 79
FeIDS 0.4% Fe + Killex 0.6% 98
FeHEDTA 0.4% Fe + Killex" 0.6% 92

-
CA 02625415 2008-03-12
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- 17 -
Table 15. Phytotoxicity (%) on Perennial iyegrass.
Perennial Ryegrass Phytotoxicity (%)
A29
Control 0
FeMGDA 0.4% Fe 0
FeIDS 0.4% Fe 0
FeHEDTA 0.4% Fe 0
Killex 0.6% 0
FeMGDA 0,4% Fe + Killex e 0.6% 0
FeIDS 0.4% Fe + Killex e 0.6% 0
FeHEDTA 0.4% Fe + Killex 0.6% 0
EXAMPLE 6
Objective: To evaluate the combination of FeIDS and/or FeHEDTA metal
chelates with Killex .
Materials and Methods: Plots Vs m2 in size were marked out in white clover and

Park Lawn (turfgrass mixture comprising of 65% perennial ryegrass, 25%
chewings/creeping red fescue and 10% Kentucky bluegrass) area in the field.
Herbicide
io solutions were prepared using deionized water. All treatments were
replicated twice.
The treatments were applied using a hand trigger sprayer at 200 ml/m2. All
treatments
were applied once. Phytotoxicity (%) was assessed on 7 days after treatment
(A7).
Table 16. Plant stages at the commencement of this study.
White clover Park Lawn
Leaf # 20+
Plant Height (cm) 3-12 3-11
Growth Stage vegetative vegetative
Coverage (%) 68 33

CA 02625415 2008-03-12
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- 18 -
Table 17. Phytotoxicity (%) against white clover.
White clover Phytotoxicity (%)
A7
Control 0
FeIDS 0.4% Fe 15
FeHEDTA 0.4% Fe 48
FeIDS 0.2% Fe + FeHEDTA 0.2% Fe 38
Killex 0.6% 23
FeIDS 0.4% Fe + Killexe 0.6% 69
FeHEDTA 0.4% Fe + Killexe 0.6% 91
FeIDS 0.2% Fe + FeHEDTA 0.2% Fe + Killexe 0.6% 85
Table 18. Phytotoxicity (%) on Park Lawn.
Park Lawn Phytotoxicity (%)
A7
Control 0
FeIDS 0.4% Fe 0
FeHEDTA 0.4% Fe 3
FeIDS 0.2% Fe + FeHEDTA 0.2% Fe 1
Killexe 0.6% 0
FeIDS 0.4% Fe + Killexe 0.6% 0
FeHEDTA 0.4% Fe + Killex 0.6% 2
FeIDS 0.2% Fe + FeHEDTA 0.2% Fe + 0.6% 0
EXAMPLE 7
Objective: To evaluate the combination of Cu-, Mn- or ZnHEDTA metal
chelates with Killex .
Materials and Methods: This trial was conducted in the greenhouse. Ten white
io clover plants and 10 pots of perennial ryegrass were selected for each
treatment.
Herbicide solutions were prepared using deionized water. The treatments were
applied

CA 02625415 2008-03-12
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- 19 -
using a hand-trigger sprayer at 200 ml/m2. All treatments were applied once.
Phytotoxicity (%) was assessed 4 and 7 days after treatment (A4 and A7).
Table 19. Plant stages at the commencement of this study.
White clover Perennial ryegrass
Leaf # 20+
Plant Height (cm) 3-16 2
Growth Stage veg veg
Table 20. Phytotoxicity (%) against white clover.
White clover Phytotoxicity (%)
A4 A7
Control 0 0
CuHEDTA 0.4% Cu 32 62
MnHEDTA 0.4% Mn 9 12
ZnHEDTA 0.4% Zn 4 3
Killex 0.6% 18 23
CuHEDTA 0.4% Cu + Killex 0.6% 46 69
=
MnHEDTA 0.4% Mn + Killex 0.6% 33 49
ZnHEDTA 0.4% Zn + Killex 0.6% 36 44

CA 02625415 2014-04-29
- 20 -
Table 21. Phytotoxicity (%) on perennial rye grass.
Perennial ryegrass Phylotoxieity (%)
A4 A7
Control 0 0
CuHIEDTA 0.4% Cu 3 3
MnHEDTA 0.4% Mn 1 1
ZnHEDTA 0.4% Zn 1 0
Killex 0.6% 1 1
CuREDTA 0.4% Cu + Killex 0.6% 3 2
MnHEDTA 0.4% Mn + Killex 0.6% 2 3
ZnHEDTA 0.4% Zn + Killex 0.6% 2 2
One skilled in the art will appreciate further features and advantages of the
invention based on the above-described embodiments. Accordingly, the invention
is not
to be limited by what has been particularly shown and described, except as
indicated by
the appended claims.

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Administrative Status

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Administrative Status

Title Date
Forecasted Issue Date 2015-05-05
(22) Filed 2008-03-12
(41) Open to Public Inspection 2008-09-14
Examination Requested 2013-01-07
(45) Issued 2015-05-05
Deemed Expired 2020-03-12

Abandonment History

There is no abandonment history.

Payment History

Fee Type Anniversary Year Due Date Amount Paid Paid Date
Application Fee $400.00 2008-03-12
Maintenance Fee - Application - New Act 2 2010-03-12 $100.00 2010-02-23
Maintenance Fee - Application - New Act 3 2011-03-14 $100.00 2011-02-25
Maintenance Fee - Application - New Act 4 2012-03-12 $100.00 2012-02-22
Request for Examination $800.00 2013-01-07
Maintenance Fee - Application - New Act 5 2013-03-12 $200.00 2013-03-11
Maintenance Fee - Application - New Act 6 2014-03-12 $200.00 2014-02-20
Maintenance Fee - Application - New Act 7 2015-03-12 $200.00 2015-02-12
Final Fee $300.00 2015-02-13
Maintenance Fee - Patent - New Act 8 2016-03-14 $200.00 2016-02-23
Maintenance Fee - Patent - New Act 9 2017-03-13 $200.00 2017-03-03
Maintenance Fee - Patent - New Act 10 2018-03-12 $250.00 2018-02-14
Maintenance Fee - Patent - New Act 11 2019-03-12 $250.00 2019-02-21
Owners on Record

Note: Records showing the ownership history in alphabetical order.

Current Owners on Record
W. NEUDORFF GMBH KG
Past Owners on Record
DIEBOLD, R. SHANE
MORGAN, KIM F.
WILSON, CAMERON D.
Past Owners that do not appear in the "Owners on Record" listing will appear in other documentation within the application.
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Document
Description 
Date
(yyyy-mm-dd) 
Number of pages   Size of Image (KB) 
Abstract 2008-03-12 1 16
Description 2008-03-12 20 757
Claims 2008-03-12 4 120
Cover Page 2008-09-02 1 30
Abstract 2014-04-29 1 12
Description 2014-04-29 21 767
Claims 2014-04-29 4 125
Claims 2014-10-23 4 125
Cover Page 2015-04-17 1 30
Correspondence 2008-05-01 1 17
Correspondence 2008-04-14 2 69
Assignment 2008-03-12 3 101
Fees 2010-02-23 1 52
Fees 2011-02-25 1 51
Fees 2012-02-22 1 52
Prosecution-Amendment 2013-01-07 1 53
Fees 2013-03-11 1 55
Prosecution-Amendment 2013-11-05 4 202
Fees 2014-02-20 1 52
Correspondence 2015-02-13 1 57
Prosecution-Amendment 2014-04-29 20 685
Prosecution-Amendment 2014-07-14 2 57
Prosecution-Amendment 2014-10-23 7 219
Fees 2015-02-12 1 54
Correspondence 2016-11-22 3 114
Maintenance Fee Payment 2016-02-23 1 53
Change of Agent 2016-02-25 4 122
Office Letter 2016-03-16 1 20
Office Letter 2016-03-16 1 24